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 ?



