data_General
_audit_creation_date                    2018-09-21
_audit_creation_method                 'by CrystalStructure 4.0'
_audit_update_record                    ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic           ?
_journal_date_from_coeditor             ?
_journal_date_accepted                  ?
_journal_coeditor_code                  ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name              'ENTER NAME'
_publ_contact_author_email             'ENTER EMAIL ADDRESS'
_publ_contact_author_fax               'ENTER FAX NUMBER'
_publ_contact_author_phone             'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal                'ENTER JOURNAL NAME HERE'
_publ_requested_category               'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name           ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
    ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2010). CrystalStructure. Version 4.0. 
    Rigaku Corporation, Tokyo, Japan.

    Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., 
    Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. 
    SIR92

    Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122.

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_AA945_HPLC1_0am

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum                  'C12 H13 Cl N2 O3'
_chemical_formula_moiety               'C12 H13 Cl N2 O3'
_chemical_formula_weight                268.70
_chemical_melting_point                 ?
_chemical_absolute_configuration        ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M         'P 1 21 1'
_symmetry_space_group_name_Hall        'P 2yb'
_symmetry_Int_Tables_number             4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1   '+X,+Y,+Z'
2   '-X,1/2+Y,-Z'
#------------------------------------------------------------------------------
_cell_length_a                          7.5174(6)
_cell_length_b                          10.8721(9)
_cell_length_c                          7.6231(6)
_cell_angle_alpha                       90.0000
_cell_angle_beta                        92.3519(10)
_cell_angle_gamma                       90.0000
_cell_volume                            622.51(9)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           2942
_cell_measurement_theta_min             2.712
_cell_measurement_theta_max             28.735
_cell_measurement_temperature           90
#------------------------------------------------------------------------------
_exptl_crystal_description              NONE
_exptl_crystal_colour                   NONE
_exptl_crystal_size_max                 0.288
_exptl_crystal_size_mid                 0.212
_exptl_crystal_size_min                 0.153
_exptl_crystal_density_diffrn           1.433
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method          'not measured'
_exptl_crystal_F_000                    280.00
_exptl_absorpt_coefficient_mu           0.308
_exptl_absorpt_correction_type          none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature             90
_diffrn_radiation_type                 'Mo K\a'
_diffrn_radiation_wavelength            0.71069
_diffrn_measurement_device_type        'CCD area detector'
_diffrn_reflns_number                   3491
_diffrn_reflns_av_R_equivalents         0.0166
_diffrn_reflns_theta_max                27.10
_diffrn_reflns_theta_full               27.10
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full    0.994
_diffrn_reflns_limit_h_min             -9
_diffrn_reflns_limit_h_max              9
_diffrn_reflns_limit_k_min             -13
_diffrn_reflns_limit_k_max              11
_diffrn_reflns_limit_l_min             -9
_diffrn_reflns_limit_l_max              8
_diffrn_standards_number                0
_diffrn_standards_interval_count        .
_diffrn_standards_decay_%               ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total                    2190
_reflns_number_gt                       2163
_reflns_threshold_expression            F²>2.0σ(F²)
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_R_factor_gt                  0.0227
_refine_ls_wR_factor_ref                0.0612
_refine_ls_number_restraints            1
_refine_ls_hydrogen_treatment           constr
_refine_ls_number_reflns                2190
_refine_ls_number_parameters            163
_refine_ls_goodness_of_fit_ref          1.055
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
           'w = 1/[σ²(Fo²)+(0.0392P)²+0.0528P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_refine_ls_shift/su_max                 0.001
_refine_diff_density_max                0.170
_refine_diff_density_min               -0.220
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?
_refine_ls_abs_structure_details
            'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  755 Friedel Pairs'
_refine_ls_abs_structure_Flack          0.49(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
  'C' 'C'  0.0033 0.0016 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.0000 0.0000 
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
  'Cl' 'Cl'  0.1484 0.1585 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'N' 'N'  0.0061 0.0033 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'O' 'O'  0.0106 0.0060 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
 Cl1 Cl 0.13652(4) 0.51337(3) 0.10711(4) 0.01548(9) Uani 1.0 2 d . . .
 O2 O 0.16475(14) 0.16409(11) 0.18234(14) 0.0174(3) Uani 1.0 2 d . . .
 O3 O 0.47970(13) 0.38265(11) 0.30331(13) 0.0144(3) Uani 1.0 2 d . . .
 O4 O -0.06816(14) 0.26659(12) 0.04458(14) 0.0216(3) Uani 1.0 2 d . . .
 N6 N 0.33013(16) 0.19576(12) 0.26257(16) 0.0158(3) Uani 1.0 2 d . . .
 N19 N 0.08123(17) 0.27483(13) 0.11833(15) 0.0152(3) Uani 1.0 2 d . . .
 C7 C 0.92174(18) 0.33415(15) 0.5431(2) 0.0144(3) Uani 1.0 2 d . . .
 C8 C 1.23354(19) 0.36191(15) 0.69360(19) 0.0128(3) Uani 1.0 2 d . . .
 C9 C 1.37779(19) 0.43560(15) 0.74839(19) 0.0155(3) Uani 1.0 2 d . . .
 C10 C 0.18961(18) 0.36667(13) 0.15760(18) 0.0122(3) Uani 1.0 2 d . . .
 C11 C 1.53333(19) 0.26042(16) 0.87332(18) 0.0168(3) Uani 1.0 2 d . . .
 C12 C 0.34250(19) 0.31523(14) 0.24618(18) 0.0129(3) Uani 1.0 2 d . . .
 C13 C 1.5253(2) 0.38635(16) 0.83799(19) 0.0169(3) Uani 1.0 2 d . . .
 C14 C 0.62442(18) 0.31267(15) 0.38952(19) 0.0149(3) Uani 1.0 2 d . . .
 C15 C 1.07157(19) 0.42096(14) 0.60237(19) 0.0146(3) Uani 1.0 2 d . . .
 C16 C 1.24435(19) 0.23547(14) 0.72778(18) 0.0142(3) Uani 1.0 2 d . . .
 C17 C 1.39360(19) 0.18566(15) 0.81650(18) 0.0170(3) Uani 1.0 2 d . . .
 C18 C 0.76973(19) 0.40155(15) 0.44450(19) 0.0148(3) Uani 1.0 2 d . . .
 H7A H 0.8757 0.2935 0.6451 0.0172 Uiso 1.0 2 calc R . .
 H7B H 0.9689 0.2714 0.4674 0.0172 Uiso 1.0 2 calc R . .
 H9 H 1.3747 0.5194 0.7242 0.0186 Uiso 1.0 2 calc R . .
 H11 H 1.6316 0.2271 0.9344 0.0201 Uiso 1.0 2 calc R . .
 H13 H 1.6191 0.4372 0.8746 0.0203 Uiso 1.0 2 calc R . .
 H14A H 0.6695 0.2520 0.3093 0.0178 Uiso 1.0 2 calc R . .
 H14B H 0.5817 0.2701 0.4914 0.0178 Uiso 1.0 2 calc R . .
 H15A H 1.1106 0.4650 0.5002 0.0175 Uiso 1.0 2 calc R . .
 H15B H 1.0235 0.4812 0.6815 0.0175 Uiso 1.0 2 calc R . .
 H16 H 1.1511 0.1842 0.6910 0.0170 Uiso 1.0 2 calc R . .
 H17 H 1.3992 0.1015 0.8376 0.0203 Uiso 1.0 2 calc R . .
 H18A H 0.7220 0.4645 0.5196 0.0178 Uiso 1.0 2 calc R . .
 H18B H 0.8146 0.4415 0.3415 0.0178 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection              Unknown
_computing_cell_refinement              Unknown
_computing_data_reduction               Unknown
_computing_structure_solution          'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement        'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material        'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics          'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cl1 C10 1.6848(15) yes . .
O2 N6 1.4056(16) yes . .
O2 N19 1.4341(18) yes . .
O3 C12 1.3243(18) yes . .
O3 C14 1.4614(18) yes . .
O4 N19 1.2383(17) yes . .
N6 C12 1.309(2) yes . .
N19 C10 1.315(2) yes . .
C7 C15 1.524(2) yes . .
C7 C18 1.529(2) yes . .
C8 C9 1.398(2) yes . .
C8 C15 1.519(2) yes . .
C8 C16 1.401(3) yes . .
C9 C13 1.386(2) yes . .
C10 C12 1.423(2) yes . .
C11 C13 1.396(3) yes . .
C11 C17 1.384(3) yes . .
C14 C18 1.505(2) yes . .
C16 C17 1.395(2) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N6 O2 N19 108.03(11) yes . . .
C12 O3 C14 114.52(13) yes . . .
O2 N6 C12 105.47(12) yes . . .
O2 N19 O4 118.03(13) yes . . .
O2 N19 C10 107.54(12) yes . . .
O4 N19 C10 134.42(15) yes . . .
C15 C7 C18 112.17(13) yes . . .
C9 C8 C15 119.45(14) yes . . .
C9 C8 C16 117.93(14) yes . . .
C15 C8 C16 122.62(13) yes . . .
C8 C9 C13 121.40(15) yes . . .
Cl1 C10 N19 121.86(11) yes . . .
Cl1 C10 C12 131.26(12) yes . . .
N19 C10 C12 106.87(13) yes . . .
C13 C11 C17 119.31(14) yes . . .
O3 C12 N6 125.13(13) yes . . .
O3 C12 C10 122.77(14) yes . . .
N6 C12 C10 112.09(13) yes . . .
C9 C13 C11 120.08(15) yes . . .
O3 C14 C18 108.02(13) yes . . .
C7 C15 C8 116.27(13) yes . . .
C8 C16 C17 120.68(14) yes . . .
C11 C17 C16 120.58(15) yes . . .
C7 C18 C14 110.40(13) yes . . .



#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
data_global
_audit_creation_method                  'APEX3 v2017.3-0'

_publ_requested_journal                 ?

_publ_contact_author_name               ?
_publ_contact_author_address            
;
;
_publ_contact_author_email              ?
_publ_contact_author_fax                ?
_publ_contact_author_phone              ?

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_HH121_3a
_chemical_name_systematic               ?
_chemical_name_common                   furoxan
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C8 H5 Cl N2 O3'
_chemical_formula_iupac                 ?
_chemical_formula_weight                212.59
_chemical_absolute_configuration        ?

_chemical_melting_point                 ?

_space_group_crystal_system             monoclinic
_space_group_name_H-M_alt               'P 1 21 1'
_space_group_name_Hall                  'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'

_cell_length_a                          6.5586(13)
_cell_length_b                          7.4628(14)
_cell_length_c                          8.5758(17)
_cell_angle_alpha                       90
_cell_angle_beta                        92.046(3)
_cell_angle_gamma                       90
_cell_volume                            419.48(14)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           1212
_cell_measurement_theta_min             2.3764
_cell_measurement_theta_max             27.4883
_cell_measurement_temperature           90.(2)

_exptl_crystal_description              block
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.067
_exptl_crystal_size_mid                 0.039
_exptl_crystal_size_min                 0.019
_exptl_crystal_density_diffrn           1.683
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    216

_exptl_absorpt_coefficient_mu           0.434
_exptl_absorpt_correction_type          Multi-Scan
_exptl_absorpt_process_details          
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min         0.89
_exptl_absorpt_correction_T_max         0.99

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             90.(2)

_diffrn_source                          'rotating-anode X-ray tube'
_diffrn_source_type                     'Bruker Turbo X-ray Source'

_diffrn_radiation_type                  MoK\a
_diffrn_radiation_source                'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_monochromator         'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type         'Bruker APEXII CCD area detector'
_diffrn_measurement_method              'phi and omega scans'

_diffrn_detector_area_resol_mean        8.3333

_diffrn_reflns_number                   2452
_diffrn_reflns_av_R_equivalents         0.0288
_diffrn_reflns_av_unetI/netI            0.0501
_diffrn_reflns_theta_min                2.38
_diffrn_reflns_theta_max                27.47
_diffrn_reflns_theta_full               27.47
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full    0.995
_diffrn_reflns_limit_h_min              -6
_diffrn_reflns_limit_h_max              8
_diffrn_reflns_limit_k_min              -9
_diffrn_reflns_limit_k_max              6
_diffrn_reflns_limit_l_min              -11
_diffrn_reflns_limit_l_max              11

_refine_special_details                 
;
;

_reflns_number_total                    1663
_reflns_number_gt                       1555
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0345
_refine_ls_R_factor_gt                  0.0312
_refine_ls_wR_factor_gt                 0.0734
_refine_ls_wR_factor_ref                0.0760
_refine_ls_goodness_of_fit_ref          1.030
_refine_ls_restrained_S_all             1.029
_refine_ls_number_reflns                1663
_refine_ls_number_parameters            127
_refine_ls_number_restraints            1
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0375P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.000
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.274
_refine_diff_density_min                -0.219
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?
_refine_ls_abs_structure_details        
;

Flack x determined using 564 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack          0.03(6)

loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    Cl Cl 0.1484 0.1585
     'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection              ?
_computing_cell_refinement              'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction               'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution           'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement         'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics           'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material         ?

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.08626(10) 0.42860(10) 0.13108(8) 0.01835(18) Uani d . . . 1 . .
    N N1 0.3826(4) 0.6391(4) 0.0445(3) 0.0164(5) Uani d . . . 1 . .
    O O1 0.3128(4) 0.7002(3) -0.0803(3) 0.0214(5) Uani d . . . 1 . .
    C C1 0.3163(4) 0.5265(4) 0.1495(3) 0.0136(6) Uani d . . . 1 . .
    O O2 0.5819(4) 0.6965(3) 0.0962(3) 0.0181(5) Uani d . . . 1 . .
    N N2 0.6292(4) 0.6130(3) 0.2390(3) 0.0162(5) Uani d . . . 1 . .
    C C2 0.4716(4) 0.5136(4) 0.2682(3) 0.0130(6) Uani d . . . 1 . .
    C C3 0.6270(4) 0.4035(4) 0.4979(3) 0.0144(6) Uani d . . . 1 . .
    O O3 0.4525(3) 0.4115(3) 0.3942(2) 0.0157(4) Uani d . . . 1 . .
    C C4 0.7970(5) 0.3093(4) 0.4533(4) 0.0156(6) Uani d . . . 1 . .
    H H4 0.800463 0.253225 0.354027 0.019 Uiso calc U . R 1 . .
    C C5 0.9629(5) 0.2994(4) 0.5590(3) 0.0163(6) Uani d . . . 1 . .
    H H5 1.082769 0.237394 0.531227 0.02 Uiso calc U . R 1 . .
    C C6 0.9541(5) 0.3798(4) 0.7048(3) 0.0172(7) Uani d . . . 1 . .
    H H6 1.068072 0.373447 0.776143 0.021 Uiso calc U . R 1 . .
    C C7 0.7790(5) 0.4690(4) 0.7461(3) 0.0177(7) Uani d . . . 1 . .
    H H7 0.772941 0.522318 0.846375 0.021 Uiso calc U . R 1 . .
    C C8 0.6126(5) 0.4812(4) 0.6427(3) 0.0155(7) Uani d . . . 1 . .
    H H8 0.491803 0.541612 0.670952 0.019 Uiso calc U . R 1 . .


_geom_special_details                   
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C1 . 1.679(3) ?
    N1 O1 . 1.236(3) ?
    N1 C1 . 1.317(4) ?
    N1 O2 . 1.431(3) ?
    C1 C2 . 1.418(4) ?
    O2 N2 . 1.399(3) ?
    N2 C2 . 1.304(4) ?
    C2 O3 . 1.331(3) ?
    C3 C8 . 1.377(4) ?
    C3 C4 . 1.384(4) ?
    C3 O3 . 1.425(3) ?
    C4 C5 . 1.393(4) ?
    C4 H4 . 0.95 ?
    C5 C6 . 1.390(4) ?
    C5 H5 . 0.95 ?
    C6 C7 . 1.384(4) ?
    C6 H6 . 0.95 ?
    C7 C8 . 1.384(4) ?
    C7 H7 . 0.95 ?
    C8 H8 . 0.95 ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 N1 C1 . . 134.9(3) ?
    O1 N1 O2 . . 117.7(2) ?
    C1 N1 O2 . . 107.4(2) ?
    N1 C1 C2 . . 106.8(3) ?
    N1 C1 Cl1 . . 122.1(2) ?
    C2 C1 Cl1 . . 131.2(2) ?
    N2 O2 N1 . . 108.0(2) ?
    C2 N2 O2 . . 105.7(2) ?
    N2 C2 O3 . . 125.4(3) ?
    N2 C2 C1 . . 112.2(3) ?
    O3 C2 C1 . . 122.4(3) ?
    C8 C3 C4 . . 123.0(3) ?
    C8 C3 O3 . . 117.8(3) ?
    C4 C3 O3 . . 119.1(2) ?
    C2 O3 C3 . . 115.7(2) ?
    C3 C4 C5 . . 117.8(3) ?
    C3 C4 H4 . . 121.1 ?
    C5 C4 H4 . . 121.1 ?
    C6 C5 C4 . . 120.4(3) ?
    C6 C5 H5 . . 119.8 ?
    C4 C5 H5 . . 119.8 ?
    C7 C6 C5 . . 119.9(3) ?
    C7 C6 H6 . . 120.0 ?
    C5 C6 H6 . . 120.0 ?
    C8 C7 C6 . . 120.7(3) ?
    C8 C7 H7 . . 119.6 ?
    C6 C7 H7 . . 119.6 ?
    C3 C8 C7 . . 118.1(3) ?
    C3 C8 H8 . . 120.9 ?
    C7 C8 H8 . . 120.9 ?



data_General
_audit_creation_date                    2018-03-19
_audit_creation_method                 'by CrystalStructure 4.0'
_audit_update_record                    ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic           ?
_journal_date_from_coeditor             ?
_journal_date_accepted                  ?
_journal_coeditor_code                  ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name              'ENTER NAME'
_publ_contact_author_email             'ENTER EMAIL ADDRESS'
_publ_contact_author_fax               'ENTER FAX NUMBER'
_publ_contact_author_phone             'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal                'ENTER JOURNAL NAME HERE'
_publ_requested_category               'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name           ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
    ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2010). CrystalStructure. Version 4.0. 
    Rigaku Corporation, Tokyo, Japan.

    M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, 
    G.L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, 
    D. Siliqi, R. Spagna (2007) 
    SIR2008

    Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122.

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_AA834_PTLC_b_0am

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum                  'C3 H3 Br N2 O3'
_chemical_formula_moiety               'C3 H3 Br N2 O3'
_chemical_formula_weight                194.97
_chemical_melting_point                 ?
_chemical_absolute_configuration        ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M         'P 1 21 1'
_symmetry_space_group_name_Hall        'P 2yb'
_symmetry_Int_Tables_number             4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1   '+X,+Y,+Z'
2   '-X,1/2+Y,-Z'
#------------------------------------------------------------------------------
_cell_length_a                          6.849(6)
_cell_length_b                          6.272(5)
_cell_length_c                          7.042(6)
_cell_angle_alpha                       90.0000
_cell_angle_beta                        106.901(10)
_cell_angle_gamma                       90.0000
_cell_volume                            289.4(4)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           1360
_cell_measurement_theta_min             3.1075
_cell_measurement_theta_max             28.582
_cell_measurement_temperature           90
#------------------------------------------------------------------------------
_exptl_crystal_description              NONE
_exptl_crystal_colour                   NONE
_exptl_crystal_size_max                 0.511
_exptl_crystal_size_mid                 0.314
_exptl_crystal_size_min                 0.166
_exptl_crystal_density_diffrn           2.237
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method          'not measured'
_exptl_crystal_F_000                    188.00
_exptl_absorpt_coefficient_mu           7.050
_exptl_absorpt_correction_type          Multi-Scan
_exptl_absorpt_process_details          
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min         0.42
_exptl_absorpt_correction_T_max         0.75

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature             90
_diffrn_radiation_type                 'Mo K\a'
_diffrn_radiation_wavelength            0.71069
_diffrn_measurement_device_type        'CCD area detector'
_diffrn_reflns_number                   1556
_diffrn_reflns_av_R_equivalents         0.0242
_diffrn_reflns_theta_max                27.50
_diffrn_reflns_theta_full               27.50
_diffrn_measured_fraction_theta_max     0.983
_diffrn_measured_fraction_theta_full    0.983
_diffrn_reflns_limit_h_min             -8
_diffrn_reflns_limit_h_max              8
_diffrn_reflns_limit_k_min             -8
_diffrn_reflns_limit_k_max              7
_diffrn_reflns_limit_l_min             -9
_diffrn_reflns_limit_l_max              7
_diffrn_standards_number                0
_diffrn_standards_interval_count        .
_diffrn_standards_decay_%               ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total                    1113
_reflns_number_gt                       1085
_reflns_threshold_expression            F²>2.0σ(F²)
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_R_factor_gt                  0.0255
_refine_ls_wR_factor_ref                0.0673
_refine_ls_number_restraints            1
_refine_ls_hydrogen_treatment           constr
_refine_ls_number_reflns                1113
_refine_ls_number_parameters            82
_refine_ls_goodness_of_fit_ref          1.117
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
           'w = 1/[σ²(Fo²)+(0.0376P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_refine_ls_shift/su_max                 0.054
_refine_diff_density_max                1.020
_refine_diff_density_min               -1.280
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?
_refine_ls_abs_structure_details
            'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  402 Friedel Pairs'
_refine_ls_abs_structure_Flack          0.14(10)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
  'C' 'C'  0.0033 0.0016 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.0000 0.0000 
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
  'N' 'N'  0.0061 0.0033 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'O' 'O'  0.0106 0.0060 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'Br' 'Br'  -0.2901 2.4595 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
 Br1 Br 0.35104(4) 0.8101 0.47737(3) 0.01112(13) Uani 1.0 2 d . . .
 O1 O 0.0732(4) 0.8097(19) -0.0011(3) 0.0146(5) Uani 1.0 2 d . . .
 O2 O 0.5834(4) 0.8112(18) 0.0133(3) 0.0145(5) Uani 1.0 2 d . . .
 O5 O 0.7701(4) 0.8119(19) 0.3412(4) 0.0173(5) Uani 1.0 2 d . . .
 N1 N 0.3743(4) 0.8090(18) -0.0946(4) 0.0136(6) Uani 1.0 2 d . . .
 N7 N 0.5979(4) 0.810(2) 0.2223(4) 0.0119(5) Uani 1.0 2 d . . .
 C3 C 0.4086(5) 0.815(3) 0.2371(5) 0.0101(7) Uani 1.0 2 d . . .
 C4 C -0.0349(5) 0.814(3) -0.2129(5) 0.0171(7) Uani 1.0 2 d . . .
 C6 C 0.2749(5) 0.807(3) 0.0379(5) 0.0114(6) Uani 1.0 2 d . . .
 H4A H -0.1790 0.8031 -0.2314 0.0205 Uiso 1.0 2 calc R . .
 H4B H 0.0092 0.6962 -0.2774 0.0205 Uiso 1.0 2 calc R . .
 H4C H -0.0058 0.9453 -0.2692 0.0205 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection              Unknown
_computing_cell_refinement              Unknown
_computing_data_reduction               Unknown
_computing_structure_solution          'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement        'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material        'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics          'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C3 1.845(4) yes . .
O1 C4 1.460(4) yes . .
O1 C6 1.328(4) yes . .
O2 N1 1.413(4) yes . .
O2 N7 1.446(4) yes . .
O5 N7 1.232(3) yes . .
N1 C6 1.305(5) yes . .
N7 C3 1.331(5) yes . .
C3 C6 1.436(4) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C4 O1 C6 113.5(3) yes . . .
N1 O2 N7 107.8(3) yes . . .
O2 N1 C6 105.9(3) yes . . .
O2 N7 O5 117.4(3) yes . . .
O2 N7 C3 107.4(2) yes . . .
O5 N7 C3 135.1(3) yes . . .
Br1 C3 N7 123.0(2) yes . . .
Br1 C3 C6 130.5(3) yes . . .
N7 C3 C6 106.4(3) yes . . .
O1 C6 N1 125.4(3) yes . . .
O1 C6 C3 122.1(3) yes . . .
N1 C6 C3 112.4(3) yes . . .



#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
data_General
_audit_creation_date                    2019-09-04
_audit_creation_method                 'by CrystalStructure 4.0'
_audit_update_record                    ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic           ?
_journal_date_from_coeditor             ?
_journal_date_accepted                  ?
_journal_coeditor_code                  ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name              'ENTER NAME'
_publ_contact_author_email             'ENTER EMAIL ADDRESS'
_publ_contact_author_fax               'ENTER FAX NUMBER'
_publ_contact_author_phone             'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal                'ENTER JOURNAL NAME HERE'
_publ_requested_category               'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name           ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
    ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2010). CrystalStructure. Version 4.0. 
    Rigaku Corporation, Tokyo, Japan.

    M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, 
    G.L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, 
    D. Siliqi, R. Spagna (2007) 
    SIR2008

    Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122.

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_AA990PTLCb2_0ama

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum                  'C6 H11 Cl N2 O2'
_chemical_formula_moiety               'C6 H11 Cl N2 O2'
_chemical_formula_weight                178.62
_chemical_melting_point                 ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting                  triclinic
_symmetry_space_group_name_H-M         'P -1'
_symmetry_space_group_name_Hall        '-P 1'
_symmetry_Int_Tables_number             2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1   '+X,+Y,+Z'
2   '-X,-Y,-Z'
#------------------------------------------------------------------------------
_cell_length_a                          5.360(7)
_cell_length_b                          9.166(14)
_cell_length_c                          18.17(3)
_cell_angle_alpha                       94.47(3)
_cell_angle_beta                        94.802(14)
_cell_angle_gamma                       101.150(16)
_cell_volume                            869(2)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           1510
_cell_measurement_theta_min             2.2605
_cell_measurement_theta_max             26.456
_cell_measurement_temperature           90
#------------------------------------------------------------------------------
_exptl_crystal_description              NONE
_exptl_crystal_colour                   NONE
_exptl_crystal_size_max                 0.140
_exptl_crystal_size_mid                 0.052
_exptl_crystal_size_min                 0.046
_exptl_crystal_density_diffrn           1.366
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method          'not measured'
_exptl_crystal_F_000                    376.00
_exptl_absorpt_coefficient_mu           0.395
_exptl_absorpt_correction_type          none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature             90
_diffrn_radiation_type                 'Mo K\a'
_diffrn_radiation_wavelength            0.71069
_diffrn_measurement_device_type        'CCD area detector'
_diffrn_reflns_number                   7234
_diffrn_reflns_av_R_equivalents         0.0191
_diffrn_reflns_theta_max                25.34
_diffrn_reflns_theta_full               25.34
_diffrn_measured_fraction_theta_max     0.949
_diffrn_measured_fraction_theta_full    0.949
_diffrn_reflns_limit_h_min             -6
_diffrn_reflns_limit_h_max              6
_diffrn_reflns_limit_k_min             -11
_diffrn_reflns_limit_k_max              6
_diffrn_reflns_limit_l_min             -18
_diffrn_reflns_limit_l_max              21
_diffrn_standards_number                0
_diffrn_standards_interval_count        .
_diffrn_standards_decay_%               ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total                    3023
_reflns_number_gt                       2469
_reflns_threshold_expression            F²>2.0σ(F²)
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_R_factor_gt                  0.1346
_refine_ls_wR_factor_ref                0.4165
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_number_reflns                3023
_refine_ls_number_parameters            199
_refine_ls_goodness_of_fit_ref          1.082
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
          'w = 1/[σ²(Fo²)+(0.1727P)²+26.4447P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_refine_ls_shift/su_max                 0.000
_refine_diff_density_max                1.940
_refine_diff_density_min               -0.880
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
  'C' 'C'  0.0033 0.0016 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.0000 0.0000 
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
  'Cl' 'Cl'  0.1484 0.1585 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'N' 'N'  0.0061 0.0033 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'O' 'O'  0.0106 0.0060 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
 Cl1 Cl 0.3007(5) 0.2930(3) 0.40257(14) 0.0224(7) Uani 1.0 2 d . . .
 Cl2 Cl 0.3817(5) 0.8193(3) 1.09719(15) 0.0239(7) Uani 1.0 2 d . . .
 O1 O 0.2067(13) -0.0026(8) 0.5744(4) 0.0198(16) Uani 1.0 2 d . . .
 O2 O 0.8320(15) 1.0086(9) 1.0706(5) 0.0277(18) Uani 1.0 2 d . . .
 O17 O 0.7806(15) 0.4885(9) 0.4290(5) 0.0280(18) Uani 1.0 2 d . . .
 O18 O 0.1519(14) 0.4625(8) 0.9241(4) 0.0205(16) Uani 1.0 2 d . . .
 N3 N 0.2408(16) 0.5861(9) 0.9776(5) 0.0169(18) Uani 1.0 2 d . . .
 N14 N 0.2518(16) 0.1009(9) 0.5206(5) 0.0169(18) Uani 1.0 2 d . . .
 N15 N 0.7477(16) 0.3909(9) 0.4850(5) 0.0212(19) Uani 1.0 2 d . . .
 N16 N 0.7585(16) 0.8907(9) 1.0123(5) 0.0194(19) Uani 1.0 2 d . . .
 C2 C 0.604(2) 0.6434(12) 0.8988(7) 0.022(3) Uani 1.0 2 d . . .
 C3 C 0.5543(19) 0.7997(11) 1.0215(6) 0.018(2) Uani 1.0 2 d . . .
 C4 C 0.4739(19) 0.1859(11) 0.5324(7) 0.021(3) Uani 1.0 2 d . . .
 C5 C 0.4542(19) 0.6698(11) 0.9636(6) 0.019(3) Uani 1.0 2 d . . .
 C6 C 0.5316(19) 0.2965(11) 0.4768(6) 0.019(3) Uani 1.0 2 d . . .
 C7 C 0.569(2) 0.7490(13) 0.8375(7) 0.025(3) Uani 1.0 2 d . . .
 C8 C 0.637(3) 0.2883(12) 0.6644(7) 0.027(3) Uani 1.0 2 d . . .
 C9 C 0.871(3) 0.3140(13) 0.7248(7) 0.029(3) Uani 1.0 2 d . . .
 C10 C 0.293(3) 0.7183(13) 0.7994(7) 0.028(3) Uani 1.0 2 d . . .
 C11 C 0.254(3) 0.8344(14) 0.7445(7) 0.034(3) Uani 1.0 2 d . . .
 C12 C 0.947(3) 0.1712(14) 0.7505(7) 0.030(3) Uani 1.0 2 d . . .
 C13 C 0.673(2) 0.1841(12) 0.5960(6) 0.020(2) Uani 1.0 2 d . . .
 H2A H 0.5495 0.5405 0.8776 0.0267 Uiso 1.0 2 calc R . .
 H2B H 0.7843 0.6587 0.9164 0.0267 Uiso 1.0 2 calc R . .
 H7A H 0.6137 0.8518 0.8595 0.0302 Uiso 1.0 2 calc R . .
 H7B H 0.6853 0.7369 0.8004 0.0302 Uiso 1.0 2 calc R . .
 H8A H 0.4835 0.2443 0.6859 0.0324 Uiso 1.0 2 calc R . .
 H8B H 0.6142 0.3838 0.6484 0.0324 Uiso 1.0 2 calc R . .
 H9A H 1.0170 0.3730 0.7054 0.0348 Uiso 1.0 2 calc R . .
 H9B H 0.8328 0.3723 0.7678 0.0348 Uiso 1.0 2 calc R . .
 H10A H 0.2542 0.6193 0.7729 0.0341 Uiso 1.0 2 calc R . .
 H10B H 0.1749 0.7204 0.8370 0.0341 Uiso 1.0 2 calc R . .
 H11A H 0.0806 0.8116 0.7220 0.0412 Uiso 1.0 2 calc R . .
 H11B H 0.2888 0.9324 0.7707 0.0412 Uiso 1.0 2 calc R . .
 H11C H 0.3681 0.8314 0.7067 0.0412 Uiso 1.0 2 calc R . .
 H12A H 1.0919 0.1978 0.7873 0.0356 Uiso 1.0 2 calc R . .
 H12B H 0.8066 0.1130 0.7714 0.0356 Uiso 1.0 2 calc R . .
 H12C H 0.9912 0.1137 0.7088 0.0356 Uiso 1.0 2 calc R . .
 H13A H 0.8418 0.2167 0.5806 0.0236 Uiso 1.0 2 calc R . .
 H13B H 0.6594 0.0829 0.6098 0.0236 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection              Unknown
_computing_cell_refinement              Unknown
_computing_data_reduction               Unknown
_computing_structure_solution          'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement        'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material        'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics          'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cl1 C6 1.747(11) yes . .
Cl2 C3 1.738(12) yes . .
O1 N14 1.418(12) yes . .
O2 N16 1.426(11) yes . .
O17 N15 1.407(13) yes . .
O18 N3 1.413(10) yes . .
N3 C5 1.304(13) yes . .
N14 C4 1.282(12) yes . .
N15 C6 1.294(12) yes . .
N16 C3 1.273(13) yes . .
C2 C5 1.512(16) yes . .
C2 C7 1.554(17) yes . .
C3 C5 1.508(14) yes . .
C4 C6 1.494(16) yes . .
C4 C13 1.509(15) yes . .
C7 C10 1.546(15) yes . .
C8 C9 1.566(17) yes . .
C8 C13 1.555(16) yes . .
C9 C12 1.539(19) yes . .
C10 C11 1.545(19) yes . .
C2 H2A 0.970 no . .
C2 H2B 0.970 no . .
C7 H7A 0.970 no . .
C7 H7B 0.970 no . .
C8 H8A 0.970 no . .
C8 H8B 0.970 no . .
C9 H9A 0.970 no . .
C9 H9B 0.970 no . .
C10 H10A 0.970 no . .
C10 H10B 0.970 no . .
C11 H11A 0.960 no . .
C11 H11B 0.960 no . .
C11 H11C 0.960 no . .
C12 H12A 0.960 no . .
C12 H12B 0.960 no . .
C12 H12C 0.960 no . .
C13 H13A 0.970 no . .
C13 H13B 0.970 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O18 N3 C5 113.2(9) yes . . .
O1 N14 C4 112.7(9) yes . . .
O17 N15 C6 114.4(9) yes . . .
O2 N16 C3 113.2(9) yes . . .
C5 C2 C7 112.3(10) yes . . .
Cl2 C3 N16 123.1(8) yes . . .
Cl2 C3 C5 118.1(7) yes . . .
N16 C3 C5 118.8(10) yes . . .
N14 C4 C6 114.8(10) yes . . .
N14 C4 C13 126.2(10) yes . . .
C6 C4 C13 119.0(8) yes . . .
N3 C5 C2 126.2(9) yes . . .
N3 C5 C3 113.7(10) yes . . .
C2 C5 C3 120.1(8) yes . . .
Cl1 C6 N15 122.3(9) yes . . .
Cl1 C6 C4 118.0(7) yes . . .
N15 C6 C4 119.7(10) yes . . .
C2 C7 C10 112.6(9) yes . . .
C9 C8 C13 111.8(10) yes . . .
C8 C9 C12 115.4(9) yes . . .
C7 C10 C11 112.0(10) yes . . .
C4 C13 C8 111.0(10) yes . . .
C5 C2 H2A 109.149 no . . .
C5 C2 H2B 109.155 no . . .
C7 C2 H2A 109.149 no . . .
C7 C2 H2B 109.153 no . . .
H2A C2 H2B 107.871 no . . .
C2 C7 H7A 109.063 no . . .
C2 C7 H7B 109.072 no . . .
C10 C7 H7A 109.076 no . . .
C10 C7 H7B 109.075 no . . .
H7A C7 H7B 107.828 no . . .
C9 C8 H8A 109.244 no . . .
C9 C8 H8B 109.247 no . . .
C13 C8 H8A 109.254 no . . .
C13 C8 H8B 109.252 no . . .
H8A C8 H8B 107.927 no . . .
C8 C9 H9A 108.432 no . . .
C8 C9 H9B 108.435 no . . .
C12 C9 H9A 108.431 no . . .
C12 C9 H9B 108.429 no . . .
H9A C9 H9B 107.473 no . . .
C7 C10 H10A 109.217 no . . .
C7 C10 H10B 109.219 no . . .
C11 C10 H10A 109.223 no . . .
C11 C10 H10B 109.212 no . . .
H10A C10 H10B 107.914 no . . .
C10 C11 H11A 109.469 no . . .
C10 C11 H11B 109.479 no . . .
C10 C11 H11C 109.465 no . . .
H11A C11 H11B 109.472 no . . .
H11A C11 H11C 109.472 no . . .
H11B C11 H11C 109.470 no . . .
C9 C12 H12A 109.473 no . . .
C9 C12 H12B 109.468 no . . .
C9 C12 H12C 109.462 no . . .
H12A C12 H12B 109.479 no . . .
H12A C12 H12C 109.472 no . . .
H12B C12 H12C 109.473 no . . .
C4 C13 H13A 109.430 no . . .
C4 C13 H13B 109.431 no . . .
C8 C13 H13A 109.424 no . . .
C8 C13 H13B 109.423 no . . .
H13A C13 H13B 108.039 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O18 N3 C5 C2 -0.9(14) no . . . .
O18 N3 C5 C3 -178.5(7) no . . . .
O1 N14 C4 C6 179.6(7) no . . . .
O1 N14 C4 C13 -1.2(14) no . . . .
O17 N15 C6 Cl1 -0.6(14) no . . . .
O17 N15 C6 C4 179.5(8) no . . . .
O2 N16 C3 Cl2 0.7(14) no . . . .
O2 N16 C3 C5 179.8(8) no . . . .
C5 C2 C7 C10 -66.0(10) no . . . .
C7 C2 C5 N3 103.7(11) no . . . .
C7 C2 C5 C3 -78.9(11) no . . . .
Cl2 C3 C5 N3 0.9(13) no . . . .
Cl2 C3 C5 C2 -176.9(7) no . . . .
N16 C3 C5 N3 -178.3(9) no . . . .
N16 C3 C5 C2 3.9(15) no . . . .
N14 C4 C6 Cl1 -2.2(14) no . . . .
N14 C4 C6 N15 177.7(9) no . . . .
N14 C4 C13 C8 -88.3(12) no . . . .
C6 C4 C13 C8 90.9(11) no . . . .
C13 C4 C6 Cl1 178.6(8) no . . . .
C13 C4 C6 N15 -1.5(15) no . . . .
C2 C7 C10 C11 174.1(8) no . . . .
C9 C8 C13 C4 -168.3(8) no . . . .
C13 C8 C9 C12 -53.4(12) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Cl1 O17 2.817(8) no . .
Cl1 N14 2.877(10) no . .
Cl2 O2 2.788(9) no . .
Cl2 N3 2.870(9) no . .
O1 C8 3.378(12) no . .
O1 C13 2.721(12) no . .
O18 C2 2.756(13) no . .
O18 C10 3.410(15) no . .
N3 N16 3.512(11) no . .
N3 C7 3.483(15) no . .
N3 C10 3.558(16) no . .
N14 N15 3.518(12) no . .
N14 C8 3.326(13) no . .
N15 C8 3.528(16) no . .
N15 C13 2.874(15) no . .
N16 C2 2.887(14) no . .
N16 C7 3.332(15) no . .
C3 C7 3.347(17) no . .
C5 C10 3.126(17) no . .
C6 C8 3.416(17) no . .
C12 C13 3.079(16) no . .
Cl1 O1 3.496(8) no . 2_556
Cl1 N15 3.477(10) no . 2_666
Cl2 O18 3.436(8) no . 2_567
Cl2 N16 3.596(10) no . 2_677
Cl2 C12 3.408(14) no . 2_667
O1 Cl1 3.496(8) no . 2_556
O1 O1 3.359(11) no . 2_556
O1 N14 2.833(11) no . 2_556
O1 C4 3.268(14) no . 2_656
O1 C6 3.374(14) no . 2_656
O1 C11 3.546(16) no . 1_545
O1 C13 3.567(13) no . 2_656
O2 O2 3.268(13) no . 2_777
O2 N16 2.815(13) no . 2_777
O2 C3 3.385(14) no . 2_677
O2 C10 3.504(15) no . 2_677
O17 O17 3.309(12) no . 2_766
O17 N15 2.836(11) no . 2_766
O17 C4 3.559(14) no . 2_666
O17 C6 3.293(14) no . 2_666
O18 Cl2 3.436(8) no . 2_567
O18 O18 3.409(12) no . 2_567
O18 N3 2.865(12) no . 2_567
O18 C3 3.288(14) no . 2_667
O18 C5 3.278(14) no . 2_667
N3 O18 2.865(12) no . 2_567
N3 N3 2.965(12) no . 2_567
N3 N3 3.520(13) no . 2_667
N3 C2 3.355(15) no . 2_667
N3 C5 3.300(15) no . 2_667
N14 O1 2.833(11) no . 2_556
N14 N14 2.964(11) no . 2_556
N14 C4 3.367(15) no . 2_656
N14 C13 3.342(14) no . 2_656
N15 Cl1 3.477(10) no . 2_666
N15 O17 2.836(11) no . 2_766
N15 N15 3.017(12) no . 2_766
N15 C6 3.529(15) no . 2_666
N16 Cl2 3.596(10) no . 2_677
N16 O2 2.815(13) no . 2_777
N16 N16 3.040(12) no . 2_777
C2 N3 3.355(15) no . 2_667
C3 O2 3.385(14) no . 2_677
C3 O18 3.288(14) no . 2_667
C4 O1 3.268(14) no . 2_656
C4 O17 3.559(14) no . 2_666
C4 N14 3.367(15) no . 2_656
C4 C4 3.588(15) no . 2_656
C5 O18 3.278(14) no . 2_667
C5 N3 3.300(15) no . 2_667
C5 C5 3.577(16) no . 2_667
C6 O1 3.374(14) no . 2_656
C6 O17 3.293(14) no . 2_666
C6 N15 3.529(15) no . 2_666
C10 O2 3.504(15) no . 2_677
C11 O1 3.546(16) no . 1_565
C12 Cl2 3.408(14) no . 2_667
C13 O1 3.567(13) no . 2_656
C13 N14 3.342(14) no . 2_656
O1 H8A 2.9857 no . .
O1 H13A 3.5914 no . .
O1 H13B 2.4169 no . .
O18 H2A 2.3610 no . .
O18 H2B 3.5363 no . .
O18 H10A 3.2354 no . .
O18 H10B 2.9344 no . .
N3 H2A 2.6209 no . .
N3 H2B 3.1745 no . .
N3 H10B 2.9457 no . .
N14 H8A 3.2282 no . .
N14 H8B 3.4990 no . .
N14 H13A 3.2029 no . .
N14 H13B 2.6480 no . .
N15 H8B 3.1133 no . .
N15 H13A 2.5330 no . .
N16 H2B 2.6744 no . .
N16 H7A 2.7948 no . .
C2 H10A 2.8003 no . .
C2 H10B 2.7165 no . .
C3 H2A 3.3874 no . .
C3 H2B 2.7314 no . .
C3 H7A 3.0503 no . .
C4 H8A 2.7943 no . .
C4 H8B 2.6288 no . .
C5 H7A 2.7028 no . .
C5 H7B 3.3635 no . .
C5 H10A 3.5079 no . .
C5 H10B 2.7592 no . .
C6 H8B 3.1291 no . .
C6 H13A 2.6480 no . .
C6 H13B 3.3335 no . .
C7 H11A 3.3824 no . .
C7 H11B 2.7474 no . .
C7 H11C 2.7473 no . .
C8 H12A 3.4327 no . .
C8 H12B 2.8180 no . .
C8 H12C 2.8180 no . .
C9 H13A 2.6835 no . .
C9 H13B 2.8510 no . .
C10 H2A 2.7321 no . .
C10 H2B 3.3990 no . .
C11 H7A 2.6956 no . .
C11 H7B 2.7800 no . .
C12 H8A 2.8783 no . .
C12 H8B 3.4329 no . .
C12 H13A 3.1661 no . .
C12 H13B 2.8476 no . .
C13 H9A 2.8218 no . .
C13 H9B 3.4038 no . .
C13 H12B 3.3476 no . .
C13 H12C 2.7523 no . .
H2A H7A 2.8545 no . .
H2A H7B 2.4063 no . .
H2A H10A 2.6062 no . .
H2A H10B 2.9184 no . .
H2B H7A 2.4054 no . .
H2B H7B 2.3298 no . .
H7A H10A 2.8480 no . .
H7A H10B 2.4121 no . .
H7A H11A 3.5772 no . .
H7A H11B 2.5295 no . .
H7A H11C 2.9478 no . .
H7B H10A 2.3478 no . .
H7B H10B 2.8481 no . .
H7B H11B 3.0748 no . .
H7B H11C 2.6185 no . .
H8A H9A 2.8556 no . .
H8A H9B 2.3459 no . .
H8A H12B 2.7389 no . .
H8A H12C 3.1873 no . .
H8A H13A 2.8541 no . .
H8A H13B 2.3310 no . .
H8B H9A 2.3386 no . .
H8B H9B 2.3974 no . .
H8B H13A 2.4564 no . .
H8B H13B 2.8538 no . .
H9A H12A 2.3405 no . .
H9A H12B 2.8320 no . .
H9A H12C 2.3597 no . .
H9A H13A 2.5869 no . .
H9A H13B 3.2422 no . .
H9B H12A 2.3405 no . .
H9B H12B 2.3597 no . .
H9B H12C 2.8321 no . .
H9B H13A 3.5920 no . .
H10A H11A 2.3610 no . .
H10A H11B 2.8441 no . .
H10A H11C 2.3726 no . .
H10B H11A 2.3609 no . .
H10B H11B 2.3726 no . .
H10B H11C 2.8439 no . .
H12B H13B 2.9531 no . .
H12C H13A 2.6988 no . .
H12C H13B 2.3816 no . .
Cl1 H8B 3.1324 no . 2_666
Cl1 H11A 2.8897 no . 2_566
Cl1 H11C 3.0678 no . 2_666
Cl1 H13B 3.4846 no . 2_656
Cl2 H2A 3.4501 no . 2_667
Cl2 H7A 3.0510 no . 2_677
Cl2 H9B 3.2847 no . 2_667
Cl2 H11B 3.3085 no . 2_677
Cl2 H12A 3.4149 no . 2_667
Cl2 H12A 3.4092 no . 2_767
Cl2 H12B 2.7425 no . 2_667
O1 H11A 3.3337 no . 1_545
O1 H11C 3.0929 no . 1_545
O1 H12C 2.9956 no . 1_455
O1 H13A 3.0660 no . 1_455
O1 H13A 3.2658 no . 2_656
O1 H13B 3.2799 no . 1_455
O1 H13B 3.5323 no . 2_656
O2 H2B 3.3115 no . 2_777
O2 H7A 3.2245 no . 2_677
O2 H7A 3.1179 no . 2_777
O2 H10B 2.8958 no . 2_677
O2 H11B 3.0381 no . 2_677
O2 H12A 3.3597 no . 2_767
O17 H8B 2.9218 no . 2_666
O17 H9A 3.0223 no . 2_766
O17 H11C 3.5980 no . 2_666
O17 H13A 3.0730 no . 2_766
O18 H2A 3.4904 no . 1_455
O18 H2B 2.9155 no . 1_455
O18 H2B 3.1997 no . 2_667
O18 H9B 3.1542 no . 1_455
O18 H12A 3.2852 no . 1_455
N3 H2A 3.1655 no . 2_667
N3 H2B 2.8210 no . 1_455
N3 H2B 3.0600 no . 2_667
N14 H13A 2.8748 no . 1_455
N14 H13A 3.2483 no . 2_656
N14 H13B 2.9245 no . 2_656
C2 H10B 3.3126 no . 1_655
C4 H13B 3.3564 no . 2_656
C5 H2A 3.5917 no . 2_667
C6 H11C 3.5656 no . 2_666
C7 H10B 3.3084 no . 1_655
C7 H11A 3.5764 no . 1_655
C9 H8A 3.5792 no . 1_655
C9 H10A 3.1471 no . 1_655
C10 H2B 3.5805 no . 1_455
C10 H7B 3.2951 no . 1_455
C10 H9A 3.4713 no . 1_455
C10 H9B 3.5950 no . 1_455
C11 H7B 3.2750 no . 1_455
C11 H12B 3.4890 no . 1_565
C11 H12C 3.2334 no . 1_465
C12 H8A 3.1666 no . 1_655
C12 H11A 3.5135 no . 1_645
C12 H11B 3.1362 no . 1_645
H2A Cl2 3.4501 no . 2_667
H2A O18 3.4904 no . 1_655
H2A N3 3.1655 no . 2_667
H2A C5 3.5917 no . 2_667
H2A H9B 3.0981 no . .
H2B O2 3.3115 no . 2_777
H2B O18 2.9155 no . 1_655
H2B O18 3.1997 no . 2_667
H2B N3 2.8210 no . 1_655
H2B N3 3.0600 no . 2_667
H2B C10 3.5805 no . 1_655
H2B H10B 2.6380 no . 1_655
H7A Cl2 3.0510 no . 2_677
H7A O2 3.2245 no . 2_677
H7A O2 3.1179 no . 2_777
H7A H10B 3.4919 no . 1_655
H7A H12B 3.0469 no . 1_565
H7B C10 3.2951 no . 1_655
H7B C11 3.2750 no . 1_655
H7B H9B 3.5965 no . .
H7B H10A 3.4857 no . 1_655
H7B H10B 2.6882 no . 1_655
H7B H11A 2.6612 no . 1_655
H7B H11B 3.4887 no . 1_655
H7B H12B 3.4730 no . 1_565
H8A C9 3.5792 no . 1_455
H8A C12 3.1666 no . 1_455
H8A H9A 2.9986 no . 1_455
H8A H11B 3.3810 no . 1_545
H8A H12A 2.8990 no . 1_455
H8A H12C 2.7589 no . 1_455
H8B Cl1 3.1324 no . 2_666
H8B O17 2.9218 no . 2_666
H8B H9A 3.4316 no . 1_455
H9A O17 3.0223 no . 2_766
H9A C10 3.4713 no . 1_655
H9A H8A 2.9986 no . 1_655
H9A H8B 3.4316 no . 1_655
H9A H10A 2.5332 no . 1_655
H9B Cl2 3.2847 no . 2_667
H9B O18 3.1542 no . 1_655
H9B C10 3.5950 no . 1_655
H9B H2A 3.0981 no . .
H9B H7B 3.5965 no . .
H9B H10A 2.8615 no . 1_655
H9B H10B 3.4424 no . 1_655
H10A C9 3.1471 no . 1_455
H10A H7B 3.4857 no . 1_455
H10A H9A 2.5332 no . 1_455
H10A H9B 2.8615 no . 1_455
H10B O2 2.8958 no . 2_677
H10B C2 3.3126 no . 1_455
H10B C7 3.3084 no . 1_455
H10B H2B 2.6380 no . 1_455
H10B H7A 3.4919 no . 1_455
H10B H7B 2.6882 no . 1_455
H10B H9B 3.4424 no . 1_455
H11A Cl1 2.8897 no . 2_566
H11A O1 3.3337 no . 1_565
H11A C7 3.5764 no . 1_455
H11A C12 3.5135 no . 1_465
H11A H7B 2.6612 no . 1_455
H11A H12B 3.4635 no . 1_465
H11A H12C 2.9239 no . 1_465
H11B Cl2 3.3085 no . 2_677
H11B O2 3.0381 no . 2_677
H11B C12 3.1362 no . 1_465
H11B H7B 3.4887 no . 1_455
H11B H8A 3.3810 no . 1_565
H11B H12A 2.8377 no . 1_465
H11B H12B 3.3286 no . 1_465
H11B H12B 2.9421 no . 1_565
H11B H12C 2.7540 no . 1_465
H11C Cl1 3.0678 no . 2_666
H11C O1 3.0929 no . 1_565
H11C O17 3.5980 no . 2_666
H11C C6 3.5656 no . 2_666
H11C H12B 3.2076 no . 1_565
H11C H12C 3.5777 no . 1_465
H11C H13B 3.2490 no . 1_565
H12A Cl2 3.4149 no . 2_667
H12A Cl2 3.4092 no . 2_767
H12A O2 3.3597 no . 2_767
H12A O18 3.2852 no . 1_655
H12A H8A 2.8990 no . 1_655
H12A H11B 2.8377 no . 1_645
H12B Cl2 2.7425 no . 2_667
H12B C11 3.4890 no . 1_545
H12B H7A 3.0469 no . 1_545
H12B H7B 3.4730 no . 1_545
H12B H11A 3.4635 no . 1_645
H12B H11B 2.9421 no . 1_545
H12B H11B 3.3286 no . 1_645
H12B H11C 3.2076 no . 1_545
H12C O1 2.9956 no . 1_655
H12C C11 3.2334 no . 1_645
H12C H8A 2.7589 no . 1_655
H12C H11A 2.9239 no . 1_645
H12C H11B 2.7540 no . 1_645
H12C H11C 3.5777 no . 1_645
H13A O1 3.0660 no . 1_655
H13A O1 3.2658 no . 2_656
H13A O17 3.0730 no . 2_766
H13A N14 2.8748 no . 1_655
H13A N14 3.2483 no . 2_656
H13B Cl1 3.4846 no . 2_656
H13B O1 3.2799 no . 1_655
H13B O1 3.5323 no . 2_656
H13B N14 2.9245 no . 2_656
H13B C4 3.3564 no . 2_656
H13B H11C 3.2490 no . 1_545

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
data_global
_audit_creation_method                  'APEX3 v2017.3-0'

_publ_requested_journal                 ?

_publ_contact_author_name               ?
_publ_contact_author_address            
;
;
_publ_contact_author_email              ?
_publ_contact_author_fax                ?
_publ_contact_author_phone              ?

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_AA1010
_chemical_name_systematic               ?
_chemical_name_common                   furoxan
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C10 H5 Cl N2 O2'
_chemical_formula_iupac                 ?
_chemical_formula_weight                220.61

_chemical_melting_point                 ?

_space_group_crystal_system             triclinic
_space_group_name_H-M_alt               'P -1'
_space_group_name_Hall                  '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'

_cell_length_a                          6.6670(13)
_cell_length_b                          6.7899(14)
_cell_length_c                          11.050(2)
_cell_angle_alpha                       81.39(3)
_cell_angle_beta                        86.15(3)
_cell_angle_gamma                       75.78(3)
_cell_volume                            479.18(18)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           479
_cell_measurement_theta_min             3.14
_cell_measurement_theta_max             25.196
_cell_measurement_temperature           90.(2)

_exptl_crystal_description              block
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.154
_exptl_crystal_size_mid                 0.028
_exptl_crystal_size_min                 0.028
_exptl_crystal_density_diffrn           1.529
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    224

_exptl_absorpt_coefficient_mu           0.376
_exptl_absorpt_correction_type          Multi-Scan
_exptl_absorpt_process_details          
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min         0.34
_exptl_absorpt_correction_T_max         0.99

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             90.(2)

_diffrn_source                          'rotating-anode X-ray tube'
_diffrn_source_type                     'Bruker Turbo X-ray Source'

_diffrn_radiation_type                  MoK\a
_diffrn_radiation_source                'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_monochromator         'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type         'Bruker APEXII CCD area detector'
_diffrn_measurement_method              'phi and omega scans'

_diffrn_detector_area_resol_mean        8.3333

_diffrn_reflns_number                   2171
_diffrn_reflns_av_R_equivalents         0.0458
_diffrn_reflns_av_unetI/netI            0.0888
_diffrn_reflns_theta_min                1.86
_diffrn_reflns_theta_max                24.40
_diffrn_reflns_theta_full               24.40
_diffrn_measured_fraction_theta_max     0.982
_diffrn_measured_fraction_theta_full    0.982
_diffrn_reflns_limit_h_min              -7
_diffrn_reflns_limit_h_max              4
_diffrn_reflns_limit_k_min              -7
_diffrn_reflns_limit_k_max              7
_diffrn_reflns_limit_l_min              -11
_diffrn_reflns_limit_l_max              12

_refine_special_details                 
;
;

_reflns_number_total                    1548
_reflns_number_gt                       969
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.2031
_refine_ls_R_factor_gt                  0.1618
_refine_ls_wR_factor_gt                 0.3953
_refine_ls_wR_factor_ref                0.4356
_refine_ls_goodness_of_fit_ref          1.550
_refine_ls_restrained_S_all             1.579
_refine_ls_number_reflns                1548
_refine_ls_number_parameters            136
_refine_ls_number_restraints            186
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 4.284
_refine_ls_shift/su_mean                0.095
_refine_diff_density_max                2.454
_refine_diff_density_min                -1.035
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    Cl Cl 0.1484 0.1585
     'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection              ?
_computing_cell_refinement              'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_reduction               'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution           'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement         'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics           'shelXle (C.B. Huebschle, rev 833)'
_computing_publication_material         ?

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.6053(4) 0.1504(5) 0.8591(2) 0.0461(12) Uani d U . . 1 . .
    C C1 0.3738(17) 0.2147(15) 0.8214(8) 0.031(2) Uani d U . . 1 . .
    O O1 0.0385(13) 0.2998(11) 0.8437(6) 0.043(2) Uani d U . . 1 . .
    N N1 0.0821(16) 0.3120(13) 0.7158(9) 0.043(2) Uani d U . . 1 . .
    O O2 -0.0526(8) 0.3636(7) 0.6376(4) 0.0050(13) Uani d U . . 1 . .
    C C2 0.3004(17) 0.2605(14) 0.7065(9) 0.033(2) Uani d U . . 1 . .
    N N2 0.2269(14) 0.2374(12) 0.9082(7) 0.033(2) Uani d U . . 1 . .
    C C5 0.6100(14) 0.2485(13) 0.3813(8) 0.021(2) Uani d U . . 1 . .
    C C4 0.5019(15) 0.2510(13) 0.4942(8) 0.023(2) Uani d U . . 1 . .
    C C3 0.4125(17) 0.2557(15) 0.5927(9) 0.032(2) Uani d U . . 1 . .
    C C8 0.8174(18) 0.2361(16) 0.1571(10) 0.040(3) Uani d U . . 1 . .
    H H8 0.88908 0.230661 0.079929 0.049 Uiso calc U . R 1 . .
    C C7 0.9241(17) 0.1907(18) 0.2585(11) 0.044(3) Uani d U . . 1 . .
    H H7 1.070962 0.152886 0.252237 0.052 Uiso calc U . R 1 . .
    C C6 0.8267(16) 0.1968(16) 0.3752(10) 0.035(2) Uani d U . . 1 . .
    H H6 0.905053 0.167044 0.447163 0.042 Uiso calc U . R 1 . .
    C C9 0.6073(18) 0.2902(16) 0.1616(9) 0.037(2) Uani d U . . 1 . .
    H H9 0.533422 0.32278 0.087769 0.045 Uiso calc U . R 1 . .
    C C10 0.5011(16) 0.2979(15) 0.2723(8) 0.030(2) Uani d U . . 1 . .
    H H10 0.354047 0.33674 0.275007 0.035 Uiso calc U . R 1 . .


_geom_special_details                   
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C1 . 1.565(12) ?
    C1 N2 . 1.321(11) ?
    C1 C2 . 1.357(15) ?
    O1 N1 . 1.419(11) ?
    O1 N2 . 1.426(12) ?
    N1 O2 . 1.238(12) ?
    N1 C2 . 1.411(15) ?
    C2 C3 . 1.419(12) ?
    C5 C4 . 1.399(11) ?
    C5 C6 . 1.400(14) ?
    C5 C10 . 1.403(14) ?
    C4 C3 . 1.206(13) ?
    C8 C7 . 1.324(16) ?
    C8 C9 . 1.358(16) ?
    C8 H8 . 0.95 ?
    C7 C6 . 1.405(14) ?
    C7 H7 . 0.95 ?
    C6 H6 . 0.95 ?
    C9 C10 . 1.373(13) ?
    C9 H9 . 0.95 ?
    C10 H10 . 0.95 ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 C1 C2 . . 113.6(10) ?
    N2 C1 Cl1 . . 118.8(8) ?
    C2 C1 Cl1 . . 127.5(8) ?
    N1 O1 N2 . . 109.9(7) ?
    O2 N1 C2 . . 132.3(8) ?
    O2 N1 O1 . . 123.9(8) ?
    C2 N1 O1 . . 103.8(9) ?
    C1 C2 N1 . . 108.1(9) ?
    C1 C2 C3 . . 128.9(10) ?
    N1 C2 C3 . . 123.0(10) ?
    C1 N2 O1 . . 104.5(8) ?
    C4 C5 C6 . . 120.9(9) ?
    C4 C5 C10 . . 120.0(9) ?
    C6 C5 C10 . . 119.2(8) ?
    C3 C4 C5 . . 178.3(11) ?
    C4 C3 C2 . . 177.8(12) ?
    C7 C8 C9 . . 121.1(9) ?
    C7 C8 H8 . . 119.5 ?
    C9 C8 H8 . . 119.5 ?
    C8 C7 C6 . . 122.0(10) ?
    C8 C7 H7 . . 119.0 ?
    C6 C7 H7 . . 119.0 ?
    C5 C6 C7 . . 117.5(11) ?
    C5 C6 H6 . . 121.2 ?
    C7 C6 H6 . . 121.2 ?
    C8 C9 C10 . . 120.3(11) ?
    C8 C9 H9 . . 119.9 ?
    C10 C9 H9 . . 119.9 ?
    C9 C10 C5 . . 119.9(10) ?
    C9 C10 H10 . . 120.0 ?
    C5 C10 H10 . . 120.1 ?



data_General
_audit_creation_date                    2019-09-04
_audit_creation_method                 'by CrystalStructure 4.0'
_audit_update_record                    ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic           ?
_journal_date_from_coeditor             ?
_journal_date_accepted                  ?
_journal_coeditor_code                  ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name              'ENTER NAME'
_publ_contact_author_email             'ENTER EMAIL ADDRESS'
_publ_contact_author_fax               'ENTER FAX NUMBER'
_publ_contact_author_phone             'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal                'ENTER JOURNAL NAME HERE'
_publ_requested_category               'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name           ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
    ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2010). CrystalStructure. Version 4.0. 
    Rigaku Corporation, Tokyo, Japan.

    M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, 
    G.L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, 
    D. Siliqi, R. Spagna (2007) 
    SIR2008

    Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122.

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_AA1010_PTLC_b_0am

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum                  'C10 H6 Cl2 N2 O2'
_chemical_formula_moiety               'C10 H6 Cl2 N2 O2'
_chemical_formula_weight                257.08
_chemical_melting_point                 ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting                  triclinic
_symmetry_space_group_name_H-M         'P -1'
_symmetry_space_group_name_Hall        '-P 1'
_symmetry_Int_Tables_number             2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1   '+X,+Y,+Z'
2   '-X,-Y,-Z'
#------------------------------------------------------------------------------
_cell_length_a                          5.5643(19)
_cell_length_b                          9.865(4)
_cell_length_c                          10.798(4)
_cell_angle_alpha                       112.164(5)
_cell_angle_beta                        95.909(6)
_cell_angle_gamma                       103.111(5)
_cell_volume                            522.8(4)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           802
_cell_measurement_theta_min             2.328
_cell_measurement_theta_max             27.59
_cell_measurement_temperature           90
#------------------------------------------------------------------------------
_exptl_crystal_description              NONE
_exptl_crystal_colour                   NONE
_exptl_crystal_size_max                 0.331
_exptl_crystal_size_mid                 0.041
_exptl_crystal_size_min                 0.040
_exptl_crystal_density_diffrn           1.633
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method          'not measured'
_exptl_crystal_F_000                    260.00
_exptl_absorpt_coefficient_mu           0.603
_exptl_absorpt_correction_type          none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature             90
_diffrn_radiation_type                 'Mo K\a'
_diffrn_radiation_wavelength            0.71069
_diffrn_measurement_device_type        'CCD area detector'
_diffrn_reflns_number                   2303
_diffrn_reflns_av_R_equivalents         0.0276
_diffrn_reflns_theta_max                23.81
_diffrn_reflns_theta_full               23.82
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full    0.989
_diffrn_reflns_limit_h_min             -6
_diffrn_reflns_limit_h_max              6
_diffrn_reflns_limit_k_min             -10
_diffrn_reflns_limit_k_max              11
_diffrn_reflns_limit_l_min             -12
_diffrn_reflns_limit_l_max              7
_diffrn_standards_number                0
_diffrn_standards_interval_count        .
_diffrn_standards_decay_%               ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total                    1590
_reflns_number_gt                       1261
_reflns_threshold_expression            F²>2.0σ(F²)
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_R_factor_gt                  0.0373
_refine_ls_wR_factor_ref                0.0889
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_number_reflns                1590
_refine_ls_number_parameters            153
_refine_ls_goodness_of_fit_ref          1.042
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
           'w = 1/[σ²(Fo²)+(0.0377P)²+0.0569P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_refine_ls_shift/su_max                 0.003
_refine_diff_density_max                0.280
_refine_diff_density_min               -0.300
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
  'C' 'C'  0.0033 0.0016 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.0000 0.0000 
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
  'Cl' 'Cl'  0.1484 0.1585 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'N' 'N'  0.0061 0.0033 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'O' 'O'  0.0106 0.0060 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
 Cl1 Cl 0.38545(13) 0.26090(8) -0.16471(8) 0.0176(3) Uani 1.0 2 d . . .
 Cl2 Cl -0.24604(14) 0.02780(8) -0.38089(9) 0.0225(3) Uani 1.0 2 d . . .
 O1 O -0.1668(4) 0.0931(2) -0.0667(3) 0.0170(5) Uani 1.0 2 d . . .
 O13 O 0.0844(4) -0.2638(3) -0.3757(3) 0.0226(6) Uani 1.0 2 d . . .
 N11 N -0.0966(5) -0.2169(3) -0.4345(3) 0.0210(7) Uani 1.0 2 d . . .
 N12 N 0.2252(5) -0.1475(3) -0.2531(3) 0.0171(6) Uani 1.0 2 d . . .
 C2 C 0.0877(6) 0.5433(4) 0.2546(4) 0.0186(8) Uani 1.0 2 d . . .
 C3 C 0.3739(6) 0.3402(4) 0.1877(4) 0.0149(7) Uani 1.0 2 d . . .
 C4 C 0.3103(6) 0.5712(4) 0.3438(4) 0.0174(8) Uani 1.0 2 d . . .
 C5 C 0.1349(6) -0.0325(3) -0.2338(4) 0.0132(7) Uani 1.0 2 d . . .
 C6 C 0.1487(5) 0.3100(3) 0.0992(3) 0.0112(7) Uani 1.0 2 d . . .
 C7 C 0.4519(6) 0.4686(4) 0.3096(4) 0.0183(8) Uani 1.0 2 d . . .
 C8 C 0.0047(6) 0.4137(3) 0.1343(4) 0.0146(7) Uani 1.0 2 d . . .
 C9 C -0.0630(6) -0.0767(3) -0.3478(4) 0.0142(7) Uani 1.0 2 d . . .
 C10 C 0.2470(6) 0.1135(3) -0.1111(4) 0.0126(7) Uani 1.0 2 d . . .
 C14 C 0.0526(6) 0.1679(3) -0.0270(4) 0.0128(7) Uani 1.0 2 d . . .
 H2 H -0.0069 0.6133 0.2806 0.0298 Uiso 1.0 2 calc R . .
 H3 H 0.4726 0.2683 0.1664 0.0095 Uiso 1.0 2 calc R . .
 H4 H 0.3637 0.6581 0.4258 0.0208 Uiso 1.0 2 calc R . .
 H7 H 0.6002 0.4864 0.3692 0.0219 Uiso 1.0 2 calc R . .
 H8 H -0.1462 0.3949 0.0762 0.0175 Uiso 1.0 2 calc R . .
 H10 H 0.3794 0.1011 -0.0526 0.0151 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection              Unknown
_computing_cell_refinement              Unknown
_computing_data_reduction               Unknown
_computing_structure_solution          'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement        'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material        'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics          'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cl1 C10 1.806(4) yes . .
Cl2 C9 1.705(4) yes . .
O1 C14 1.210(4) yes . .
O13 N11 1.390(4) yes . .
O13 N12 1.385(3) yes . .
N11 C9 1.301(4) yes . .
N12 C5 1.298(5) yes . .
C2 C4 1.391(5) yes . .
C2 C8 1.375(4) yes . .
C3 C6 1.394(5) yes . .
C3 C7 1.379(4) yes . .
C4 C7 1.386(5) yes . .
C5 C9 1.420(5) yes . .
C5 C10 1.484(4) yes . .
C6 C8 1.405(5) yes . .
C6 C14 1.475(4) yes . .
C10 C14 1.543(5) yes . .
C2 H2 0.939 no . .
C3 H3 0.967 no . .
C4 H4 0.930 no . .
C7 H7 0.930 no . .
C8 H8 0.930 no . .
C10 H10 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N11 O13 N12 110.9(2) yes . . .
O13 N11 C9 103.8(3) yes . . .
O13 N12 C5 106.4(3) yes . . .
C4 C2 C8 120.7(4) yes . . .
C6 C3 C7 120.4(3) yes . . .
C2 C4 C7 119.6(3) yes . . .
N12 C5 C9 107.6(3) yes . . .
N12 C5 C10 120.4(3) yes . . .
C9 C5 C10 132.0(3) yes . . .
C3 C6 C8 119.2(3) yes . . .
C3 C6 C14 121.3(3) yes . . .
C8 C6 C14 119.4(3) yes . . .
C3 C7 C4 120.3(3) yes . . .
C2 C8 C6 119.8(3) yes . . .
Cl2 C9 N11 119.9(3) yes . . .
Cl2 C9 C5 128.8(3) yes . . .
N11 C9 C5 111.3(3) yes . . .
Cl1 C10 C5 108.9(3) yes . . .
Cl1 C10 C14 107.4(3) yes . . .
C5 C10 C14 113.3(3) yes . . .
O1 C14 C6 123.8(3) yes . . .
O1 C14 C10 119.1(3) yes . . .
C6 C14 C10 117.1(3) yes . . .
C4 C2 H2 118.150 no . . .
C8 C2 H2 121.103 no . . .
C6 C3 H3 120.221 no . . .
C7 C3 H3 119.293 no . . .
C2 C4 H4 120.218 no . . .
C7 C4 H4 120.210 no . . .
C3 C7 H7 119.858 no . . .
C4 C7 H7 119.852 no . . .
C2 C8 H8 120.113 no . . .
C6 C8 H8 120.124 no . . .
Cl1 C10 H10 109.027 no . . .
C5 C10 H10 109.024 no . . .
C14 C10 H10 109.032 no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N11 O13 N12 C5 0.9(4) no . . . .
N12 O13 N11 C9 -0.3(3) no . . . .
O13 N11 C9 Cl2 179.2(3) no . . . .
O13 N11 C9 C5 -0.4(4) no . . . .
O13 N12 C5 C9 -1.1(4) no . . . .
O13 N12 C5 C10 -179.1(3) no . . . .
C4 C2 C8 C6 -1.4(6) no . . . .
C8 C2 C4 C7 1.1(6) no . . . .
C6 C3 C7 C4 -1.7(6) no . . . .
C7 C3 C6 C8 1.4(5) no . . . .
C7 C3 C6 C14 -175.6(3) no . . . .
C2 C4 C7 C3 0.5(6) no . . . .
N12 C5 C9 Cl2 -178.5(3) no . . . .
N12 C5 C9 N11 1.0(4) no . . . .
N12 C5 C10 Cl1 115.1(4) no . . . .
N12 C5 C10 C14 -125.4(4) no . . . .
C9 C5 C10 Cl1 -62.3(5) no . . . .
C9 C5 C10 C14 57.2(5) no . . . .
C10 C5 C9 Cl2 -0.9(6) no . . . .
C10 C5 C9 N11 178.7(4) no . . . .
C3 C6 C8 C2 0.2(5) no . . . .
C3 C6 C14 O1 138.1(4) no . . . .
C3 C6 C14 C10 -41.6(5) no . . . .
C8 C6 C14 O1 -38.9(6) no . . . .
C8 C6 C14 C10 141.3(3) no . . . .
C14 C6 C8 C2 177.2(3) no . . . .
Cl1 C10 C14 O1 118.9(3) no . . . .
Cl1 C10 C14 C6 -61.4(4) no . . . .
C5 C10 C14 O1 -1.5(5) no . . . .
C5 C10 C14 C6 178.3(3) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Cl1 C3 3.595(4) no . .
Cl1 C6 3.180(4) no . .
Cl1 C9 3.387(3) no . .
Cl2 O1 3.167(3) no . .
Cl2 C10 3.489(4) no . .
Cl2 C14 3.597(4) no . .
O1 C3 3.530(3) no . .
O1 C5 2.737(4) no . .
O1 C8 2.941(3) no . .
O1 C9 3.053(4) no . .
O13 C10 3.571(3) no . .
N12 C14 3.559(4) no . .
C2 C3 2.769(5) no . .
C3 C10 3.046(4) no . .
C4 C6 2.784(4) no . .
C7 C8 2.778(5) no . .
C9 C14 3.282(4) no . .
Cl1 O1 3.566(3) no . 1_655
Cl1 C2 3.564(4) no . 2_665
Cl1 C4 3.342(4) no . 2_665
Cl1 C7 3.569(4) no . 2_665
Cl2 Cl2 3.4119(15) no . 2_454
O1 Cl1 3.566(3) no . 1_455
O1 O1 3.449(4) no . 2_555
O1 N12 3.532(3) no . 1_455
O1 N12 3.351(4) no . 2_555
O1 C5 3.509(5) no . 2_555
O1 C10 3.310(4) no . 1_455
O1 C10 3.280(5) no . 2_555
O1 C14 3.261(5) no . 2_555
O13 C2 3.465(5) no . 2_555
O13 C3 3.541(5) no . 2_555
O13 C4 3.376(5) no . 1_544
O13 C4 3.473(5) no . 2_555
O13 C6 3.515(5) no . 2_555
O13 C7 3.505(4) no . 2_555
O13 C8 3.475(5) no . 2_555
N11 C4 3.530(4) no . 1_444
N11 C7 3.484(4) no . 1_444
N11 C7 3.569(5) no . 2_555
N12 O1 3.532(3) no . 1_655
N12 O1 3.351(4) no . 2_555
N12 C3 3.420(5) no . 2_655
N12 C6 3.296(5) no . 2_555
N12 C8 3.396(5) no . 2_555
N12 C14 3.585(5) no . 2_555
C2 Cl1 3.564(4) no . 2_665
C2 O13 3.465(5) no . 2_555
C3 O13 3.541(5) no . 2_555
C3 N12 3.420(5) no . 2_655
C3 C8 3.571(5) no . 1_655
C4 Cl1 3.342(4) no . 2_665
C4 O13 3.376(5) no . 1_566
C4 O13 3.473(5) no . 2_555
C4 N11 3.530(4) no . 1_666
C5 O1 3.509(5) no . 2_555
C6 O13 3.515(5) no . 2_555
C6 N12 3.296(5) no . 2_555
C7 Cl1 3.569(4) no . 2_665
C7 O13 3.505(4) no . 2_555
C7 N11 3.484(4) no . 1_666
C7 N11 3.569(5) no . 2_555
C8 O13 3.475(5) no . 2_555
C8 N12 3.396(5) no . 2_555
C8 C3 3.571(5) no . 1_455
C10 O1 3.310(4) no . 1_655
C10 O1 3.280(5) no . 2_555
C14 O1 3.261(5) no . 2_555
C14 N12 3.585(5) no . 2_555
C14 C14 3.507(5) no . 2_555
Cl1 H3 3.5290 no . .
O1 H8 2.7564 no . .
O1 H10 3.0090 no . .
N12 H10 2.4685 no . .
C2 H7 3.2401 no . .
C3 H4 3.2372 no . .
C3 H8 3.2555 no . .
C3 H10 2.7795 no . .
C4 H3 3.2672 no . .
C4 H8 3.2432 no . .
C6 H2 3.2620 no . .
C6 H7 3.2436 no . .
C6 H10 2.7686 no . .
C7 H2 3.2373 no . .
C8 H3 3.2924 no . .
C8 H4 3.2415 no . .
C9 H10 3.3923 no . .
C10 H3 2.7909 no . .
C14 H3 2.6810 no . .
C14 H8 2.6408 no . .
H2 H4 2.3027 no . .
H2 H8 2.3272 no . .
H3 H7 2.3157 no . .
H3 H10 2.2354 no . .
H4 H7 2.3173 no . .
Cl1 H2 3.0594 no . 2_565
Cl1 H4 3.5407 no . 2_665
Cl1 H8 3.1232 no . 1_655
Cl2 H2 3.1975 no . 2_565
Cl2 H4 3.4788 no . 1_444
Cl2 H4 3.5000 no . 2_565
O1 H3 3.5608 no . 1_455
O1 H3 3.2772 no . 2_555
O1 H10 2.5623 no . 1_455
O1 H10 2.8067 no . 2_555
O13 H2 3.3819 no . 1_544
O13 H3 3.1885 no . 2_655
O13 H4 2.7544 no . 1_544
O13 H7 3.3549 no . 1_444
O13 H7 3.1221 no . 2_655
N11 H2 3.0542 no . 1_544
N11 H4 2.9664 no . 1_444
N11 H4 3.3439 no . 1_544
N11 H7 2.8720 no . 1_444
N12 H3 2.5595 no . 2_655
N12 H4 3.5357 no . 1_544
N12 H7 3.5011 no . 2_655
N12 H10 3.5848 no . 2_655
C2 H7 3.1194 no . 1_455
C3 H8 3.0605 no . 1_655
C4 H7 3.3636 no . 2_666
C7 H2 3.1280 no . 1_655
C7 H7 3.3778 no . 2_666
C7 H8 3.5208 no . 1_655
C8 H3 3.0993 no . 1_455
C8 H7 3.5433 no . 1_455
C8 H8 3.5049 no . 2_565
C9 H4 3.5746 no . 1_444
C14 H10 3.5790 no . 2_555
H2 Cl1 3.0594 no . 2_565
H2 Cl2 3.1975 no . 2_565
H2 O13 3.3819 no . 1_566
H2 N11 3.0542 no . 1_566
H2 C7 3.1280 no . 1_455
H2 H7 2.7119 no . 1_455
H3 O1 3.5608 no . 1_655
H3 O1 3.2772 no . 2_555
H3 O13 3.1885 no . 2_655
H3 N12 2.5595 no . 2_655
H3 C8 3.0993 no . 1_655
H3 H8 2.6734 no . 1_655
H4 Cl1 3.5407 no . 2_665
H4 Cl2 3.4788 no . 1_666
H4 Cl2 3.5000 no . 2_565
H4 O13 2.7544 no . 1_566
H4 N11 3.3439 no . 1_566
H4 N11 2.9664 no . 1_666
H4 N12 3.5357 no . 1_566
H4 C9 3.5746 no . 1_666
H4 H7 3.0650 no . 2_666
H7 O13 3.3549 no . 1_666
H7 O13 3.1221 no . 2_655
H7 N11 2.8720 no . 1_666
H7 N12 3.5011 no . 2_655
H7 C2 3.1194 no . 1_655
H7 C4 3.3636 no . 2_666
H7 C7 3.3778 no . 2_666
H7 C8 3.5433 no . 1_655
H7 H2 2.7119 no . 1_655
H7 H4 3.0650 no . 2_666
H7 H7 3.0827 no . 2_666
H7 H8 3.4869 no . 1_655
H8 Cl1 3.1232 no . 1_455
H8 C3 3.0605 no . 1_455
H8 C7 3.5208 no . 1_455
H8 C8 3.5049 no . 2_565
H8 H3 2.6734 no . 1_455
H8 H7 3.4869 no . 1_455
H8 H8 3.3554 no . 2_565
H8 H10 3.1674 no . 1_455
H10 O1 2.5623 no . 1_655
H10 O1 2.8067 no . 2_555
H10 N12 3.5848 no . 2_655
H10 C14 3.5790 no . 2_555
H10 H8 3.1674 no . 1_655
H10 H10 3.1114 no . 2_655

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
data_General
_audit_creation_date                    2018-12-12
_audit_creation_method                 'by CrystalStructure 4.0'
_audit_update_record                    ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic           ?
_journal_date_from_coeditor             ?
_journal_date_accepted                  ?
_journal_coeditor_code                  ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name              'ENTER NAME'
_publ_contact_author_email             'ENTER EMAIL ADDRESS'
_publ_contact_author_fax               'ENTER FAX NUMBER'
_publ_contact_author_phone             'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal                'ENTER JOURNAL NAME HERE'
_publ_requested_category               'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name           ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
    ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2010). CrystalStructure. Version 4.0. 
    Rigaku Corporation, Tokyo, Japan.

    M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, 
    G.L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, 
    D. Siliqi, R. Spagna (2007) 
    SIR2008

    Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122.

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_AA1000_2_0ama

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum                  'C64 H40 Cl8 N16 O16'
_chemical_formula_moiety               'C64 H40 Cl8 N16 O16'
_chemical_formula_weight                1572.74
_chemical_melting_point                 ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M         'P b c a'
_symmetry_space_group_name_Hall        '-P 2ac 2ab'
_symmetry_Int_Tables_number             61
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1   '+X,+Y,+Z'
2   '1/2-X,1/2+Y,+Z'
3   '+X,1/2-Y,1/2+Z'
4   '1/2-X,-Y,1/2+Z'
5   '-X,-Y,-Z'
6   '1/2+X,1/2-Y,-Z'
7   '-X,1/2+Y,1/2-Z'
8   '1/2+X,+Y,1/2-Z'
#------------------------------------------------------------------------------
_cell_length_a                          12.5251(19)
_cell_length_b                          7.7888(12)
_cell_length_c                          16.980(3)
_cell_angle_alpha                       90.0000
_cell_angle_beta                        90.0000
_cell_angle_gamma                       90.0000
_cell_volume                            1656.5(5)
_cell_formula_units_Z                   1
_cell_measurement_reflns_used           1842
_cell_measurement_theta_min             2.8985
_cell_measurement_theta_max             27.635
_cell_measurement_temperature           90
#------------------------------------------------------------------------------
_exptl_crystal_description              NONE
_exptl_crystal_colour                   NONE
_exptl_crystal_size_max                 0.168
_exptl_crystal_size_mid                 0.081
_exptl_crystal_size_min                 0.070
_exptl_crystal_density_diffrn           1.576
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method          'not measured'
_exptl_crystal_F_000                    800.00
_exptl_absorpt_coefficient_mu           0.423
_exptl_absorpt_correction_type          none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature             90
_diffrn_radiation_type                 'Mo K\a'
_diffrn_radiation_wavelength            0.71069
_diffrn_measurement_device_type        'CCD area detector'
_diffrn_reflns_number                   8812
_diffrn_reflns_av_R_equivalents         0.0516
_diffrn_reflns_theta_max                27.50
_diffrn_reflns_theta_full               27.50
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full    0.995
_diffrn_reflns_limit_h_min             -16
_diffrn_reflns_limit_h_max              14
_diffrn_reflns_limit_k_min             -10
_diffrn_reflns_limit_k_max              10
_diffrn_reflns_limit_l_min             -11
_diffrn_reflns_limit_l_max              21
_diffrn_standards_number                0
_diffrn_standards_interval_count        .
_diffrn_standards_decay_%               ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total                    1891
_reflns_number_gt                       1392
_reflns_threshold_expression            F²>2.0σ(F²)
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_R_factor_gt                  0.0365
_refine_ls_wR_factor_ref                0.0908
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           constr
_refine_ls_number_reflns                1889
_refine_ls_number_parameters            118
_refine_ls_goodness_of_fit_ref          1.012
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
           'w = 1/[σ²(Fo²)+(0.0389P)²+0.7279P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_refine_ls_shift/su_max                 0.000
_refine_diff_density_max                0.360
_refine_diff_density_min               -0.240
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
  'C' 'C'  0.0033 0.0016 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.0000 0.0000 
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
  'Cl' 'Cl'  0.1484 0.1585 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'N' 'N'  0.0061 0.0033 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'O' 'O'  0.0106 0.0060 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
 Cl1 Cl 0.40549(4) 0.33479(6) 0.45144(3) 0.02123(14) Uani 1.0 8 d . . .
 O1 O 0.36118(10) -0.10497(19) 0.53820(7) 0.0232(4) Uani 1.0 8 d . . .
 O2 O 0.34420(11) -0.30340(18) 0.43973(8) 0.0246(4) Uani 1.0 8 d . . .
 N1 N 0.35858(11) -0.1508(2) 0.45519(9) 0.0188(4) Uani 1.0 8 d . . .
 N2 N 0.37947(12) 0.0699(3) 0.54309(10) 0.0226(4) Uani 1.0 8 d . . .
 C1 C 0.37402(13) -0.0078(3) 0.32713(11) 0.0179(4) Uani 1.0 8 d . . .
 C2 C 0.45026(15) 0.0878(3) 0.28605(12) 0.0225(5) Uani 1.0 8 d . . .
 C3 C 0.37364(13) -0.0092(3) 0.41369(11) 0.0165(4) Uani 1.0 8 d . . .
 C4 C 0.29798(15) -0.1018(3) 0.28536(11) 0.0230(5) Uani 1.0 8 d . . .
 C5 C 0.29733(16) -0.0983(3) 0.20389(12) 0.0274(5) Uani 1.0 8 d . . .
 C6 C 0.44911(16) 0.0889(3) 0.20442(12) 0.0274(5) Uani 1.0 8 d . . .
 C7 C 0.38615(13) 0.1231(3) 0.47026(11) 0.0179(4) Uani 1.0 8 d . . .
 C8 C 0.37291(15) -0.0033(3) 0.16344(12) 0.0261(5) Uani 1.0 8 d . . .
 H2 H 0.5015 0.1504 0.3134 0.0270 Uiso 1.0 8 calc R . .
 H4 H 0.2476 -0.1670 0.3123 0.0276 Uiso 1.0 8 calc R . .
 H5 H 0.2460 -0.1600 0.1762 0.0328 Uiso 1.0 8 calc R . .
 H6 H 0.5000 0.1521 0.1770 0.0329 Uiso 1.0 8 calc R . .
 H8 H 0.3724 -0.0014 0.1087 0.0313 Uiso 1.0 8 calc R . .



#==============================================================================
_computing_data_collection              Unknown
_computing_cell_refinement              Unknown
_computing_data_reduction               Unknown
_computing_structure_solution          'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement        'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material        'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics          'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Cl1 C7 1.697(2) yes . .
O1 N1 1.454(2) yes . .
O1 N2 1.383(3) yes . .
O2 N1 1.230(3) yes . .
N1 C3 1.323(3) yes . .
N2 C7 1.307(3) yes . .
C1 C2 1.397(3) yes . .
C1 C3 1.470(3) yes . .
C1 C4 1.395(3) yes . .
C2 C6 1.386(3) yes . .
C3 C7 1.417(3) yes . .
C4 C5 1.384(3) yes . .
C5 C8 1.384(3) yes . .
C6 C8 1.382(3) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N1 O1 N2 107.67(13) yes . . .
O1 N1 O2 116.56(15) yes . . .
O1 N1 C3 107.97(15) yes . . .
O2 N1 C3 135.47(17) yes . . .
O1 N2 C7 105.43(16) yes . . .
C2 C1 C3 120.34(17) yes . . .
C2 C1 C4 119.50(18) yes . . .
C3 C1 C4 120.16(17) yes . . .
C1 C2 C6 119.68(19) yes . . .
N1 C3 C1 122.63(17) yes . . .
N1 C3 C7 105.13(17) yes . . .
C1 C3 C7 132.24(18) yes . . .
C1 C4 C5 120.13(19) yes . . .
C4 C5 C8 120.17(19) yes . . .
C2 C6 C8 120.50(19) yes . . .
Cl1 C7 N2 119.71(16) yes . . .
Cl1 C7 C3 126.47(15) yes . . .
N2 C7 C3 113.80(18) yes . . .
C5 C8 C6 120.01(19) yes . . .



#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
data_General
_audit_creation_date                    2019-09-04
_audit_creation_method                 'by CrystalStructure 4.0'
_audit_update_record                    ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic           ?
_journal_date_from_coeditor             ?
_journal_date_accepted                  ?
_journal_coeditor_code                  ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name              'ENTER NAME'
_publ_contact_author_email             'ENTER EMAIL ADDRESS'
_publ_contact_author_fax               'ENTER FAX NUMBER'
_publ_contact_author_phone             'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal                'ENTER JOURNAL NAME HERE'
_publ_requested_category               'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name           ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
    ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2010). CrystalStructure. Version 4.0. 
    Rigaku Corporation, Tokyo, Japan.

    Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., 
    Burla, M., Polidori, G., and Camalli, M. (1994) J. Appl. Cryst., 27, 435. 
    SIR92

    Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122.

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_AA1046_PTLCa_0am

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum                  'C12 H15 Br N2 O2'
_chemical_formula_moiety               'C12 H15 Br N2 O2'
_chemical_formula_weight                299.17
_chemical_melting_point                 ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting                  monoclinic
_symmetry_space_group_name_H-M         'P 1 21/m 1'
_symmetry_space_group_name_Hall        '-P 2yb'
_symmetry_Int_Tables_number             11
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1   '+X,+Y,+Z'
2   '-X,1/2+Y,-Z'
3   '-X,-Y,-Z'
4   '+X,1/2-Y,+Z'
#------------------------------------------------------------------------------
_cell_length_a                          9.2209
_cell_length_b                          6.6668
_cell_length_c                          9.3831
_cell_angle_alpha                       90.0000
_cell_angle_beta                        99.2121
_cell_angle_gamma                       90.0000
_cell_volume                            569.3762
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           2653
_cell_measurement_theta_min             2.8775
_cell_measurement_theta_max             28.7025
_cell_measurement_temperature           90
#------------------------------------------------------------------------------
_exptl_crystal_description              NONE
_exptl_crystal_colour                   NONE
_exptl_crystal_size_max                 0.237
_exptl_crystal_size_mid                 0.159
_exptl_crystal_size_min                 0.102
_exptl_crystal_density_diffrn           1.745
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method          'not measured'
_exptl_crystal_F_000                    304.00
_exptl_absorpt_coefficient_mu           3.611
_exptl_absorpt_correction_type          Multi-Scan
_exptl_absorpt_process_details          
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min         0.58
_exptl_absorpt_correction_T_max         0.75

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature             90
_diffrn_radiation_type                 'Mo K\a'
_diffrn_radiation_wavelength            0.71069
_diffrn_measurement_device_type        'CCD area detector'
_diffrn_reflns_number                   2833
_diffrn_reflns_av_R_equivalents         0.0193
_diffrn_reflns_theta_max                25.35
_diffrn_reflns_theta_full               25.36
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full    0.996
_diffrn_reflns_limit_h_min             -9
_diffrn_reflns_limit_h_max              11
_diffrn_reflns_limit_k_min             -6
_diffrn_reflns_limit_k_max              8
_diffrn_reflns_limit_l_min             -8
_diffrn_reflns_limit_l_max              11
_diffrn_standards_number                0
_diffrn_standards_interval_count        .
_diffrn_standards_decay_%               ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total                    1137
_reflns_number_gt                       1104
_reflns_threshold_expression            F²>2.0σ(F²)
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_R_factor_gt                  0.0178
_refine_ls_wR_factor_ref                0.0465
_refine_ls_number_restraints            0
_refine_ls_hydrogen_treatment           refxyz
_refine_ls_number_reflns                1137
_refine_ls_number_parameters            128
_refine_ls_goodness_of_fit_ref          1.077
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
           'w = 1/[σ²(Fo²)+(0.0218P)²+0.3543P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_refine_ls_shift/su_max                 0.001
_refine_diff_density_max                0.440
_refine_diff_density_min               -0.260
_refine_ls_extinction_method            SHELXL
_refine_ls_extinction_coef              0.0020(17)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
  'C' 'C'  0.0033 0.0016 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.0000 0.0000 
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
  'Br' 'Br'  -0.2901 2.4595 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'N' 'N'  0.0061 0.0033 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'O' 'O'  0.0106 0.0060 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
 Br1 Br 0.66940(2) 0.2500 0.61975(2) 0.01357(11) Uani 1.0 2 d . . .
 O2 O 0.33419(18) 0.2500 0.30708(18) 0.0154(4) Uani 1.0 2 d . . .
 O3 O 0.11560(19) 0.2500 0.38937(19) 0.0183(4) Uani 1.0 2 d . . .
 N4 N 0.2494(2) 0.2500 0.4246(2) 0.0128(4) Uani 1.0 2 d . . .
 N5 N 0.4804(2) 0.2500 0.3671(2) 0.0147(5) Uani 1.0 2 d . . .
 C6 C 0.2834(2) 0.2500 0.6909(2) 0.0105(5) Uani 1.0 2 d . . .
 C7 C 0.4834(3) 0.2500 0.5063(3) 0.0117(5) Uani 1.0 2 d . . .
 C8 C 0.3422(3) 0.2500 0.5495(2) 0.0113(5) Uani 1.0 2 d . . .
 C9 C 0.3429(3) 0.2500 0.9627(3) 0.0134(5) Uani 1.0 2 d . . .
 C10 C 0.12428(18) 0.0621(3) 0.83982(18) 0.0153(4) Uani 1.0 4 d . . .
 C11 C 0.4079(3) 0.2500 0.8216(3) 0.0128(5) Uani 1.0 2 d . . .
 C12 C 0.0299(3) 0.2500 0.8442(3) 0.0180(6) Uani 1.0 2 d . . .
 C13 C 0.24842(19) 0.0626(3) 0.96909(18) 0.0149(4) Uani 1.0 4 d . . .
 C14 C 0.18899(18) 0.0601(3) 0.69881(17) 0.0135(4) Uani 1.0 4 d . . .
 H15 H -0.047(4) 0.2500 0.763(4) 0.023(8) Uiso 1.0 2 d . . .
 H16 H -0.010(4) 0.2500 0.931(4) 0.022(8) Uiso 1.0 2 d . . .
 H17 H 0.109(3) 0.055(3) 0.615(2) 0.017(5) Uiso 1.0 4 d . . .
 H18 H 0.250(2) -0.055(3) 0.697(2) 0.010(5) Uiso 1.0 4 d . . .
 H19 H 0.465(2) 0.136(3) 0.818(2) 0.015(5) Uiso 1.0 4 d . . .
 H20 H 0.424(3) 0.2500 1.039(3) 0.011(7) Uiso 1.0 2 d . . .
 H21 H 0.306(3) -0.056(3) 0.966(2) 0.014(5) Uiso 1.0 4 d . . .
 H22 H 0.208(3) 0.062(3) 1.059(3) 0.017(5) Uiso 1.0 4 d . . .
 H23 H 0.069(3) -0.051(3) 0.843(2) 0.015(5) Uiso 1.0 4 d . . .



#==============================================================================
_computing_data_collection              Unknown
_computing_cell_refinement              Unknown
_computing_data_reduction               Unknown
_computing_structure_solution          'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement        'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material        'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics          'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C7 1.868(3) yes . .
O2 N4 1.450(3) yes . .
O2 N5 1.375(3) yes . .
O3 N4 1.225(3) yes . .
N4 C8 1.336(3) yes . .
N5 C7 1.302(4) yes . .
C6 C8 1.511(3) yes . .
C6 C11 1.540(3) yes . .
C6 C14 1.545(2) yes . .
C6 C14 1.545(2) yes . 4_555
C7 C8 1.424(4) yes . .
C9 C11 1.538(5) yes . .
C9 C13 1.530(3) yes . .
C9 C13 1.530(3) yes . 4_555
C10 C12 1.530(3) yes . .
C10 C13 1.529(3) yes . .
C10 C14 1.536(3) yes . .
C9 H20 0.95(3) no . .
C10 H23 0.91(2) no . .
C11 H19 0.93(2) no . .
C11 H19 0.93(2) no . 4_555
C12 H15 0.96(3) no . .
C12 H16 0.95(4) no . .
C13 H21 0.96(2) no . .
C13 H22 0.98(3) no . .
C14 H17 0.990(19) no . .
C14 H18 0.95(2) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N4 O2 N5 107.52(15) yes . . .
O2 N4 O3 115.92(17) yes . . .
O2 N4 C8 108.63(18) yes . . .
O3 N4 C8 135.5(3) yes . . .
O2 N5 C7 105.8(2) yes . . .
C8 C6 C11 111.88(19) yes . . .
C8 C6 C14 109.04(11) yes . . .
C8 C6 C14 109.04(11) yes . . 4_555
C11 C6 C14 108.41(12) yes . . .
C11 C6 C14 108.41(12) yes . . 4_555
C14 C6 C14 110.06(15) yes . . 4_555
Br1 C7 N5 116.2(2) yes . . .
Br1 C7 C8 129.5(2) yes . . .
N5 C7 C8 114.3(3) yes . . .
N4 C8 C6 120.0(3) yes . . .
N4 C8 C7 103.7(2) yes . . .
C6 C8 C7 136.3(2) yes . . .
C11 C9 C13 109.66(15) yes . . .
C11 C9 C13 109.66(15) yes . . 4_555
C13 C9 C13 109.5(2) yes . . 4_555
C12 C10 C13 109.51(16) yes . . .
C12 C10 C14 109.35(16) yes . . .
C13 C10 C14 109.80(14) yes . . .
C6 C11 C9 110.0(3) yes . . .
C10 C12 C10 110.0(2) yes . . 4_555
C9 C13 C10 109.23(16) yes . . .
C6 C14 C10 109.51(14) yes . . .
C11 C9 H20 106.2(19) no . . .
C13 C9 H20 110.9(9) no . . .
C13 C9 H20 110.9(9) no 4_555 . .
C12 C10 H23 110.6(13) no . . .
C13 C10 H23 109.0(12) no . . .
C14 C10 H23 108.6(13) no . . .
C6 C11 H19 109.0(12) no . . .
C6 C11 H19 109.0(12) no . . 4_555
C9 C11 H19 109.5(13) no . . .
C9 C11 H19 109.5(13) no . . 4_555
H19 C11 H19 109.8(17) no . . 4_555
C10 C12 H15 109.4(11) no . . .
C10 C12 H16 108.9(9) no . . .
C10 C12 H15 109.4(11) no 4_555 . .
C10 C12 H16 108.9(9) no 4_555 . .
H15 C12 H16 110(3) no . . .
C9 C13 H21 110.5(13) no . . .
C9 C13 H22 109.8(12) no . . .
C10 C13 H21 108.7(11) no . . .
C10 C13 H22 110.0(11) no . . .
H21 C13 H22 108.5(17) no . . .
C6 C14 H17 110.3(12) no . . .
C6 C14 H18 109.0(12) no . . .
C10 C14 H17 110.1(13) no . . .
C10 C14 H18 109.2(12) no . . .
H17 C14 H18 108.8(16) no . . .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N4 O2 N5 C7 0.0 no . . . .
N5 O2 N4 O3 180.0 no . . . .
N5 O2 N4 C8 0.0 no . . . .
O2 N4 C8 C6 180.0 no . . . .
O2 N4 C8 C7 0.0 no . . . .
O3 N4 C8 C6 0.0 no . . . .
O3 N4 C8 C7 180.0 no . . . .
O2 N5 C7 Br1 180.0 no . . . .
O2 N5 C7 C8 0.0 no . . . .
C8 C6 C11 C9 180.0 no . . . .
C11 C6 C8 N4 180.0 no . . . .
C11 C6 C8 C7 0.0 no . . . .
C8 C6 C14 C10 -178.08(13) no . . . .
C14 C6 C8 N4 60.10(11) no . . . .
C14 C6 C8 C7 -119.90(11) no . . . .
C8 C6 C14 C10 178.08(13) no . . 4_555 4_555
C14 C6 C8 N4 -60.10(11) no 4_555 . . .
C14 C6 C8 C7 119.90(11) no 4_555 . . .
C11 C6 C14 C10 59.90(17) no . . . .
C14 C6 C11 C9 -59.72(12) no . . . .
C11 C6 C14 C10 -59.90(17) no . . 4_555 4_555
C14 C6 C11 C9 59.72(12) no 4_555 . . .
C14 C6 C14 C10 58.51(16) no . . 4_555 4_555
C14 C6 C14 C10 -58.51(16) no 4_555 . . .
Br1 C7 C8 N4 180.0 no . . . .
Br1 C7 C8 C6 0.0 no . . . .
N5 C7 C8 N4 0.0 no . . . .
N5 C7 C8 C6 180.0 no . . . .
C11 C9 C13 C10 -59.7(2) no . . . .
C13 C9 C11 C6 60.15(14) no . . . .
C11 C9 C13 C10 59.7(2) no . . 4_555 4_555
C13 C9 C11 C6 -60.15(14) no 4_555 . . .
C13 C9 C13 C10 -60.7(3) no . . 4_555 4_555
C13 C9 C13 C10 60.7(3) no 4_555 . . .
C12 C10 C13 C9 -59.79(19) no . . . .
C13 C10 C12 C10 59.4(3) no . . . 4_555
C12 C10 C14 C6 59.38(16) no . . . .
C14 C10 C12 C10 -61.0(2) no . . . 4_555
C13 C10 C14 C6 -60.79(16) no . . . .
C14 C10 C13 C9 60.28(17) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
Br1 C11 3.296(3) no . .
O3 N5 3.403(3) no . .
O3 C6 3.000(3) no . .
O3 C7 3.393(4) no . .
O3 C14 3.140(3) no . .
O3 C14 3.140(3) no . 4_555
N4 C14 2.999(3) no . .
N4 C14 2.999(3) no . 4_555
C6 C10 2.516(3) no . 4_555
C6 C12 2.934(4) no . .
C6 C13 2.958(3) no . .
C6 C13 2.958(3) no . 4_555
C7 C11 3.146(5) no . .
C9 C10 2.494(3) no . 4_555
C9 C12 2.922(4) no . .
C9 C14 2.936(3) no . .
C9 C14 2.936(3) no . 4_555
C10 C11 2.929(3) no . .
C10 C13 2.932(3) no . 4_555
C10 C14 2.950(3) no . 4_555
C11 C12 3.526(4) no . .
C12 C13 2.498(3) no . 4_555
C12 C14 2.501(4) no . 4_555
C13 C14 3.552(3) no . 4_555
Br1 O2 3.4046(4) no . 2_646
Br1 O2 3.4046(4) no . 2_656
Br1 N4 3.4562(6) no . 2_646
Br1 N4 3.4562(6) no . 2_656
O2 Br1 3.4046(4) no . 2_646
O2 Br1 3.4046(4) no . 2_656
O2 C9 3.245(4) no . 1_554
O2 C13 3.383(3) no . 1_554
O2 C13 3.383(3) no . 4_554
O3 C10 3.510(2) no . 2_556
O3 C10 3.510(2) no . 3_556
O3 C14 3.479(3) no . 2_556
O3 C14 3.479(3) no . 3_556
N4 Br1 3.4562(6) no . 2_646
N4 Br1 3.4562(6) no . 2_656
N5 C7 3.5365(11) no . 2_646
N5 C7 3.5365(11) no . 2_656
C7 N5 3.5365(11) no . 2_646
C7 N5 3.5365(11) no . 2_656
C7 C7 3.3512(5) no . 2_646
C7 C7 3.3512(5) no . 2_656
C9 O2 3.245(4) no . 1_556
C10 O3 3.510(2) no . 2_546
C13 O2 3.383(3) no . 1_556
C14 O3 3.479(3) no . 2_546
Br1 H19 2.95(2) no . .
Br1 H19 2.95(2) no . 4_555
O3 H17 2.49(2) no . .
O3 H17 2.49(2) no . 4_555
O3 H18 3.589(18) no . .
O3 H18 3.589(18) no . 4_555
N4 H17 2.70(3) no . .
N4 H17 2.70(3) no . 4_555
N4 H18 3.271(19) no . .
N4 H18 3.271(19) no . 4_555
C6 H15 3.23(4) no . .
C6 H17 2.10(2) no . 4_555
C6 H18 2.06(2) no . 4_555
C6 H20 3.32(3) no . .
C6 H21 3.27(2) no . .
C6 H21 3.27(2) no . 4_555
C6 H23 3.30(2) no . .
C6 H23 3.30(2) no . 4_555
C7 H19 3.05(2) no . .
C7 H19 3.05(2) no . 4_555
C8 H17 2.67(3) no . .
C8 H17 2.67(3) no . 4_555
C8 H18 2.68(2) no . .
C8 H18 2.68(2) no . 4_555
C8 H19 2.701(19) no . .
C8 H19 2.701(19) no . 4_555
C9 H16 3.22(3) no . .
C9 H18 3.225(19) no . .
C9 H18 3.225(19) no . 4_555
C9 H21 2.07(2) no . 4_555
C9 H22 2.08(3) no . 4_555
C9 H23 3.28(2) no . .
C9 H23 3.28(2) no . 4_555
C10 H17 3.30(2) no . 4_555
C10 H19 3.22(2) no . .
C10 H20 3.33(3) no . .
C10 H22 3.26(2) no . 4_555
C10 H23 3.30(2) no . 4_555
C11 H17 3.368(19) no . .
C11 H17 3.368(19) no . 4_555
C11 H18 2.663(19) no . .
C11 H18 2.663(19) no . 4_555
C11 H21 2.70(2) no . .
C11 H21 2.70(2) no . 4_555
C11 H22 3.36(3) no . .
C11 H22 3.36(3) no . 4_555
C12 H17 2.71(2) no . .
C12 H17 2.71(2) no . 4_555
C12 H18 3.32(2) no . .
C12 H18 3.32(2) no . 4_555
C12 H21 3.32(2) no . .
C12 H21 3.32(2) no . 4_555
C12 H22 2.70(2) no . .
C12 H22 2.70(2) no . 4_555
C12 H23 2.04(2) no . 4_555
C13 H15 3.33(3) no . .
C13 H16 2.66(3) no . .
C13 H17 3.367(19) no . .
C13 H18 2.670(19) no . .
C13 H19 2.68(2) no . .
C13 H19 3.31(2) no . 4_555
C13 H21 3.34(2) no . 4_555
C13 H22 2.69(2) no . 4_555
C14 H15 2.67(3) no . .
C14 H16 3.32(4) no . .
C14 H17 2.75(2) no . 4_555
C14 H18 3.35(2) no . 4_555
C14 H19 2.661(18) no . .
C14 H19 3.308(19) no . 4_555
C14 H21 2.678(19) no . .
C14 H22 3.36(3) no . .
H15 H17 2.52(4) no . .
H15 H17 2.52(4) no . 4_555
H15 H18 3.54(4) no . .
H15 H18 3.54(4) no . 4_555
H15 H22 3.57(4) no . .
H15 H22 3.57(4) no . 4_555
H15 H23 2.34(3) no . .
H15 H23 2.34(3) no . 4_555
H16 H17 3.57(4) no . .
H16 H17 3.57(4) no . 4_555
H16 H21 3.53(4) no . .
H16 H21 3.53(4) no . 4_555
H16 H22 2.50(3) no . .
H16 H22 2.50(3) no . 4_555
H16 H23 2.33(3) no . .
H16 H23 2.33(3) no . 4_555
H17 H17 2.61(3) no . 4_555
H17 H19 3.57(3) no . .
H17 H21 3.57(3) no . .
H17 H23 2.34(3) no . .
H18 H19 2.48(3) no . .
H18 H19 3.51(3) no . 4_555
H18 H21 2.49(3) no . .
H18 H22 3.56(3) no . .
H18 H23 2.32(3) no . .
H19 H20 2.30(4) no . .
H19 H21 2.52(3) no . .
H19 H21 3.55(3) no . 4_555
H19 H22 3.57(3) no . .
H20 H21 2.36(3) no . .
H20 H21 2.36(3) no . 4_555
H20 H22 2.39(4) no . .
H20 H22 2.39(4) no . 4_555
H21 H22 3.57(3) no . 4_555
H21 H23 2.30(3) no . .
H22 H22 2.51(3) no . 4_555
H22 H23 2.34(3) no . .
Br1 H15 2.74(3) no . 1_655
Br1 H18 3.44(2) no . 2_656
Br1 H18 3.44(2) no . 3_656
O2 H19 3.48(2) no . 2_656
O2 H19 3.48(2) no . 3_656
O2 H20 2.77(3) no . 1_554
O2 H22 2.74(2) no . 1_554
O2 H22 2.74(2) no . 4_554
O3 H17 2.90(2) no . 2_556
O3 H17 2.90(2) no . 3_556
O3 H18 3.578(19) no . 2_556
O3 H18 3.578(19) no . 3_556
O3 H22 3.57(3) no . 1_554
O3 H22 3.57(3) no . 4_554
O3 H23 2.868(19) no . 2_556
O3 H23 2.868(19) no . 3_556
N5 H18 2.95(2) no . 2_656
N5 H18 2.95(2) no . 3_656
N5 H19 3.19(2) no . 2_656
N5 H19 3.19(2) no . 3_656
N5 H20 3.04(3) no . 1_554
C7 H18 3.59(2) no . 2_656
C7 H18 3.59(2) no . 3_656
C9 H19 3.579(19) no . 2_657
C9 H19 3.579(19) no . 3_657
C9 H21 3.45(2) no . 2_657
C9 H21 3.45(2) no . 3_657
C10 H16 3.28(3) no . 2_547
C10 H22 3.45(2) no . 3_557
C10 H23 3.45(2) no . 4_545
C11 H21 3.303(19) no . 2_657
C11 H21 3.303(19) no . 3_657
C12 H22 3.25(2) no . 2_557
C12 H22 3.25(2) no . 3_557
C12 H23 3.47(2) no . 2_557
C12 H23 3.47(2) no . 3_557
C13 H16 3.27(3) no . 2_547
C13 H19 3.320(18) no . 3_657
C13 H21 3.42(2) no . 4_545
C14 H18 3.41(2) no . 4_545
H15 Br1 2.74(3) no . 1_455
H15 H22 3.18(4) no . 2_557
H15 H22 3.18(4) no . 3_557
H16 C10 3.28(3) no . 2_557
H16 C10 3.28(3) no . 3_557
H16 C13 3.27(3) no . 2_557
H16 C13 3.27(3) no . 3_557
H16 H16 3.570(17) no . 2_547
H16 H16 3.570(17) no . 2_557
H16 H21 3.30(4) no . 2_557
H16 H21 3.30(4) no . 3_557
H16 H22 2.78(3) no . 2_557
H16 H22 2.78(3) no . 3_557
H16 H23 2.63(4) no . 2_557
H16 H23 2.63(4) no . 3_557
H17 O3 2.90(2) no . 2_546
H17 H17 2.80(3) no . 3_556
H18 Br1 3.44(2) no . 2_646
H18 O3 3.578(19) no . 2_546
H18 N5 2.95(2) no . 2_646
H18 C7 3.59(2) no . 2_646
H18 C14 3.41(2) no . 4_545
H18 H18 2.59(3) no . 4_545
H18 H21 3.59(3) no . 4_545
H18 H23 3.50(3) no . 4_545
H19 O2 3.48(2) no . 2_646
H19 N5 3.19(2) no . 2_646
H19 C9 3.579(19) no . 2_647
H19 C13 3.320(18) no . 3_657
H19 H20 3.00(3) no . 2_647
H19 H21 3.38(3) no . 2_657
H19 H21 2.73(3) no . 3_657
H19 H22 3.32(3) no . 3_657
H20 O2 2.77(3) no . 1_556
H20 N5 3.04(3) no . 1_556
H20 H19 3.00(3) no . 2_657
H20 H19 3.00(3) no . 3_657
H20 H21 2.81(4) no . 2_657
H20 H21 2.81(4) no . 3_657
H21 C9 3.45(2) no . 2_647
H21 C11 3.303(19) no . 2_647
H21 C13 3.42(2) no . 4_545
H21 H16 3.30(4) no . 2_547
H21 H18 3.59(3) no . 4_545
H21 H19 3.38(3) no . 2_647
H21 H19 2.73(3) no . 3_657
H21 H20 2.81(4) no . 2_647
H21 H21 2.58(3) no . 4_545
H21 H23 3.49(3) no . 4_545
H22 O2 2.74(2) no . 1_556
H22 O3 3.57(3) no . 1_556
H22 C10 3.45(2) no . 3_557
H22 C12 3.25(2) no . 2_547
H22 H15 3.18(4) no . 2_547
H22 H16 2.78(3) no . 2_547
H22 H19 3.32(3) no . 3_657
H22 H23 2.85(3) no . 3_557
H23 O3 2.868(19) no . 2_546
H23 C10 3.45(2) no . 4_545
H23 C12 3.47(2) no . 2_547
H23 H16 2.63(4) no . 2_547
H23 H18 3.50(3) no . 4_545
H23 H21 3.49(3) no . 4_545
H23 H22 2.85(3) no . 3_557
H23 H23 3.46(3) no . 3_557
H23 H23 2.65(3) no . 4_545

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
data_General
_audit_creation_date                    2018-01-26
_audit_creation_method                 'by CrystalStructure 4.0'
_audit_update_record                    ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic           ?
_journal_date_from_coeditor             ?
_journal_date_accepted                  ?
_journal_coeditor_code                  ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name              'ENTER NAME'
_publ_contact_author_email             'ENTER EMAIL ADDRESS'
_publ_contact_author_fax               'ENTER FAX NUMBER'
_publ_contact_author_phone             'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal                'ENTER JOURNAL NAME HERE'
_publ_requested_category               'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name           ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
    ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2010). CrystalStructure. Version 4.0. 
    Rigaku Corporation, Tokyo, Japan.

    M.C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, 
    G.L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, 
    D. Siliqi, R. Spagna (2007) 
    SIR2008

    Sheldrick, G.M. (2008), Acta Cryst. A64, 112-122.

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_AA807_1_5_b_0am

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum                  'C2 Br2 N2 O2'
_chemical_formula_moiety               'C2 Br2 N2 O2'
_chemical_formula_weight                243.84
_chemical_melting_point                 ?
_chemical_absolute_configuration        ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting                  orthorhombic
_symmetry_space_group_name_H-M         'P 21 21 21'
_symmetry_space_group_name_Hall        'P 2ac 2ab'
_symmetry_Int_Tables_number             19
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1   '+X,+Y,+Z'
2   '1/2+X,1/2-Y,-Z'
3   '-X,1/2+Y,1/2-Z'
4   '1/2-X,-Y,1/2+Z'
#------------------------------------------------------------------------------
_cell_length_a                          5.9208(10)
_cell_length_b                          7.7879(13)
_cell_length_c                          12.680(2)
_cell_angle_alpha                       90.0000
_cell_angle_beta                        90.0000
_cell_angle_gamma                       90.0000
_cell_volume                            584.67(17)
_cell_formula_units_Z                   4
_cell_measurement_reflns_used           2376
_cell_measurement_theta_min             3.0695
_cell_measurement_theta_max             28.579
_cell_measurement_temperature           90
#------------------------------------------------------------------------------
_exptl_crystal_description              NONE
_exptl_crystal_colour                   NONE
_exptl_crystal_size_max                 0.236
_exptl_crystal_size_mid                 0.122
_exptl_crystal_size_min                 0.090
_exptl_crystal_density_diffrn           2.770
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method          'not measured'
_exptl_crystal_F_000                    448.00
_exptl_absorpt_coefficient_mu           13.811
_exptl_absorpt_correction_type          Multi-Scan
_exptl_absorpt_process_details          
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min         0.45
_exptl_absorpt_correction_T_max         0.75

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature             90
_diffrn_radiation_type                 'Mo K\a'
_diffrn_radiation_wavelength            0.71069
_diffrn_measurement_device_type        'CCD area detector'
_diffrn_reflns_number                   3463
_diffrn_reflns_av_R_equivalents         0.0487
_diffrn_reflns_theta_max                28.63
_diffrn_reflns_theta_full               28.62
_diffrn_measured_fraction_theta_max     0.959
_diffrn_measured_fraction_theta_full    0.959
_diffrn_reflns_limit_h_min             -7
_diffrn_reflns_limit_h_max              7
_diffrn_reflns_limit_k_min             -8
_diffrn_reflns_limit_k_max              10
_diffrn_reflns_limit_l_min             -14
_diffrn_reflns_limit_l_max              16
_diffrn_standards_number                0
_diffrn_standards_interval_count        .
_diffrn_standards_decay_%               ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total                    1389
_reflns_number_gt                       1331
_reflns_threshold_expression            F²>2.0σ(F²)
_refine_ls_structure_factor_coef        Fsqd
_refine_ls_R_factor_gt                  0.0273
_refine_ls_wR_factor_ref                0.0646
_refine_ls_number_restraints            0
_refine_ls_number_reflns                1389
_refine_ls_number_parameters            73
_refine_ls_goodness_of_fit_ref          0.477
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details
          'w = 1/[σ²(Fo²)+(0.0556P)²+12.9089P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary            direct
_atom_sites_solution_secondary          difmap
_refine_ls_shift/su_max                 0.006
_refine_diff_density_max                0.890
_refine_diff_density_min               -0.670
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?
_refine_ls_abs_structure_details
            'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  528 Friedel Pairs'
_refine_ls_abs_structure_Flack          0.06(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
  'C' 'C'  0.0033 0.0016 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'N' 'N'  0.0061 0.0033 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'O' 'O'  0.0106 0.0060 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'Br' 'Br'  -0.2901 2.4595 
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
 Br1 Br 0.43774(6) 0.14645(5) 0.58657(3) 0.01531(11) Uani 1.0 4 d . . .
 Br2 Br 0.07917(6) -0.14460(6) 0.73946(3) 0.01292(11) Uani 1.0 4 d . . .
 O1 O 0.5957(5) -0.3449(4) 0.5765(3) 0.0137(6) Uani 1.0 4 d . . .
 O2 O 0.3467(6) -0.4991(4) 0.6768(3) 0.0146(7) Uani 1.0 4 d . . .
 N4 N 0.4034(6) -0.3551(5) 0.6455(3) 0.0097(6) Uani 1.0 4 d . . .
 N5 N 0.6258(7) -0.1736(5) 0.5488(3) 0.0139(7) Uani 1.0 4 d . . .
 C1 C 0.4673(7) -0.0887(5) 0.5982(4) 0.0103(7) Uani 1.0 4 d . . .
 C3 C 0.3290(7) -0.1973(5) 0.6593(3) 0.0094(8) Uani 1.0 4 d . . .



#==============================================================================
_computing_data_collection              Unknown
_computing_cell_refinement              Unknown
_computing_data_reduction               Unknown
_computing_structure_solution          'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement        'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material        'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics          'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Br1 C1 1.846(4) yes . .
Br2 C3 1.841(4) yes . .
O1 N4 1.439(5) yes . .
O1 N5 1.391(5) yes . .
O2 N4 1.236(5) yes . .
N4 C3 1.317(6) yes . .
N5 C1 1.307(6) yes . .
C1 C3 1.409(6) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
N4 O1 N5 107.9(3) yes . . .
O1 N4 O2 117.4(4) yes . . .
O1 N4 C3 107.1(3) yes . . .
O2 N4 C3 135.5(4) yes . . .
O1 N5 C1 105.8(4) yes . . .
Br1 C1 N5 122.1(3) yes . . .
Br1 C1 C3 125.7(3) yes . . .
N5 C1 C3 112.2(4) yes . . .
Br2 C3 N4 123.3(3) yes . . .
Br2 C3 C1 129.6(3) yes . . .
N4 C3 C1 107.0(4) yes . . .



#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
