data_ban17_15sn


_symmetry_space_group_name_hall   'P 2ac 2ab'
#Added by publCIF




_publ_section_figure_captions
;
The contents of the asymmetric unit are shown with the displacement ellipsoids
drawn at the 30% probability level. H atoms are shown as circles of arbitrary
radius.
;
#Added by publCIF



_publ_section_related_literature ?

_publ_contact_author_name 'Paul D. Carr'

_publ_contact_letter 
;
Please consider this CIF for publication. I certify that this contibution is the
original work of those listed as authors; that it has not been published
before (in any language or medium) and is not being considered for publication
elsewhere; that all authors concur with and are aware of the submission; that
all workers involved in the study are listed as authors or given proper credit
in the acknowledgements; that I have obtained permission for and acknowledged
the source of any excerpts from other copyright works; and that to the best of
my knowledge the paper contains no statements which are libellous, unlawful or
in any way actionable. All coauthors have made significant scientific
contributions to the work reported, including the ideas and their execution,
and share responsibility and accountability for the results.
;


_publ_requested_category ?

_publ_requested_journal ?

_publ_contact_author_fax ?

_publ_contact_author_phone ?

_publ_contact_author_email paul.carr@anu.edu.au

_publ_contact_author_address

;
Research School of Chemistry,
The Australian National University,Canberra,
ACT 2601,
Australia
;


# Loop of author details

loop_
_publ_author_name
_publ_author_address
_publ_author_footnote
_publ_author_email
'Carr, Paul D.'
;
Research School of Chemistry,
The Australian National University,Canberra,
ACT 2601,
Australia
;
.
;
paul.carr@anu.edu.au
;
'Liu, Xin'
;
Research School of Chemistry,
The Australian National University,Canberra,
ACT 2601,
Australia
;
.
.
'Banwell, Martin G.'
;
Research School of Chemistry,
The Australian National University,Canberra,
ACT 2601,
Australia
;
.
.






_publ_section_abstract
;
The structure of the title compound, C₁₃H₁₄N₂O₃, is reported and the
absolute configuration established. Data were collected at 150 K and the
crystal exhibited orthorhombic (P2₁2₁2₁) symmetry. The structure
refined with good statistics to the expected structure showing the following
chirality; R at C8, R at C9 and S at C10. The ethoxy group had rather large
displacement ellipsoids but refining them as two separate conformers did not
improve the refinement and so they were left as a single conformer in the
final model.
;


_publ_section_title
;
Structure report on compound BAN17_15SN (XL-1-13-2) C₁₃H₁₄N₂O₃
;
#Added by publCIF



# publcif _publ_body_element loop start
loop_
_publ_body_element
_publ_body_title
_publ_body_contents

 section 
;
Introduction
; 
;

;
 section 
;
Experimental
; 
;

;
 subsection 
;
Synthesis and crystallization
; 
;

;
 subsection 
;
Refinement
;
;
Crystal data, data collection and structure refinement details are summarized
in Table 1.
;

 section 
;
Results and discussion
; 
;

;
# publcif _publ_body_element loop end

_audit_update_record
;
2017-02-27 # Formatted by publCIF

;
_publcif_datablock.id '{7b9376af-dd7c-4286-9686-ff0beff9568d}'
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
'{7b9376af-dd7c-4286-9686-ff0beff9568d}' y y y

#
# add machine specifics from crysalis pro
# ban16_pc38sn_scaled.cif
#
_audit_creation_date           2017-02-17
_audit_creation_method         'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection     'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement     'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction      'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_cell_length_a                  9.26094(4) 
_cell_length_b                  9.56903(5) 
_cell_length_c                  13.38456(6) 
_cell_angle_alpha               90.0 
_cell_angle_beta                90.0 
_cell_angle_gamma               90.0 
_cell_volume                    1186.116(10) 
_cell_formula_units_Z           4
_cell_measurement_temperature   150.00(10) 
_cell_measurement_reflns_used   19989
_cell_measurement_theta_min     3.2090
_cell_measurement_theta_max     73.6650
#
# skip _cell_oxdiff_length_a  etc
#
_exptl_crystal_size_max                             0.526
_exptl_crystal_size_mid                             0.198
_exptl_crystal_size_min                             0.138
#
# add _exptl_crystal_description manually if not present
#
_exptl_crystal_description          'block'
_exptl_crystal_colour               'yellow'
#
# skip _exptl_crystal_face_index_h etc
#
_exptl_absorpt_correction_T_min                   0.76706
_exptl_absorpt_correction_T_max                   1.00000
_exptl_absorpt_correction_type            multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
#
# skip _oxdiff_exptl_absorpt_empirical_full_min   etc
#
_diffrn_ambient_temperature 150.00(10) 
_diffrn_ambient_environment N~2~
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54184
_diffrn_radiation_monochromator mirror
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector 'CCD plate'
_diffrn_detector_type EosS2
_diffrn_detector_area_resol_mean 8.1297
_diffrn_reflns_number 24123
_diffrn_reflns_av_R_equivalents 0.0373
_diffrn_reflns_av_sigmaI/netI 0.0290
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 3.3019
_diffrn_reflns_theta_max 73.8344
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_reflns_theta_full 74.3338
_diffrn_measured_fraction_theta_full 0.9875
_diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0358144000
_diffrn_orient_matrix_UB_12       0.0068485000
_diffrn_orient_matrix_UB_13       0.1123435000
_diffrn_orient_matrix_UB_21       0.0156101000
_diffrn_orient_matrix_UB_22      -0.1598935000
_diffrn_orient_matrix_UB_23       0.0073277000
_diffrn_orient_matrix_UB_31       0.1616887000
_diffrn_orient_matrix_UB_32       0.0169536000
_diffrn_orient_matrix_UB_33       0.0241732000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -104.00 -20.00   1.00    1.00    --  -36.95 -57.00-120.00   84
  2  ω     18.00 106.00   1.00    1.00    --   36.95  38.00-150.00   88
  3  ω    -32.00  56.00   1.00    1.00    --   36.95 -38.00  30.00   88
  4  ω     23.00  90.00   1.00    1.00    --   36.95-125.00 120.00   67
  5  ω    -34.00  66.00   1.00    1.00    --   36.95 -19.00  90.00  100
  6  ω      1.00  76.00   1.00    1.00    --   36.95 -99.00 -90.00   75
  7  ω      1.00  76.00   1.00    1.00    --   36.95 -99.00 150.00   75
  8  ω     20.00 104.00   1.00    1.00    --   36.95  57.00   0.00   84
  9  ω     23.00  90.00   1.00    1.00    --   36.95-125.00 -90.00   67
 10  ω    -32.00  56.00   1.00    1.00    --   36.95 -38.00   0.00   88
 11  ω      1.00  76.00   1.00    1.00    --   36.95 -99.00 -30.00   75
 12  ω     41.00 116.00   1.00    2.00    --  111.00-111.00-150.00   75
 13  ω     43.00 138.00   1.00    2.00    --  111.00 -77.00 120.00   95
 14  ω     91.00 178.00   1.00    2.00    --  111.00  64.00 -30.00   87
 15  ω     41.00 136.00   1.00    2.00    --  111.00 -25.00   0.00   95
 16  ω     42.00 146.00   1.00    2.00    --  111.00 -92.00  30.00  104
 17  ω     92.00 178.00   1.00    2.00    --  111.00  38.00 150.00   86
 18  ω    100.00 178.00   1.00    2.00    --  111.00 111.00  90.00   78
 19  ω     42.00 130.00   1.00    2.00    --  111.00 -38.00 150.00   88
 20  ω     57.00 150.00   1.00    2.00    --  111.00 178.00  30.00   93
 21  ω     43.00 128.00   1.00    2.00    --  111.00 -50.00-120.00   85
 22  ω     41.00 116.00   1.00    2.00    --  111.00-111.00   0.00   75
 23  ω     44.00 131.00   1.00    2.00    --  111.00 -64.00 -60.00   87
 24  ω     44.00 131.00   1.00    2.00    --  111.00 -64.00  30.00   87
 25  ω     42.00 130.00   1.00    2.00    --  111.00 -38.00 -30.00   88
 26  ω     43.00 128.00   1.00    2.00    --  111.00 -50.00 -30.00   85
 27  ω     43.00 138.00   1.00    2.00    --  111.00 -77.00 -60.00   95
 28  ω     42.00 146.00   1.00    2.00    --  111.00 -92.00 150.00  104
 29  ω     65.00 178.00   1.00    2.00    --  111.00  12.00 -90.00  113
 30  ω     84.00 178.00   1.00    2.00    --  111.00  77.00-150.00   94
 31  ω     86.00 178.00   1.00    2.00    --  111.00  25.00 -30.00   92
 32  ω     94.00 178.00   1.00    2.00    --  111.00  50.00 120.00   84
 33  ω     41.00 116.00   1.00    2.00    --  111.00-111.00 -60.00   75
 34  ω     44.00 131.00   1.00    2.00    --  111.00 -64.00-120.00   87
 35  ω     41.00 116.00   1.00    2.00    --  111.00-111.00  30.00   75
 36  ω     41.00 116.00   1.00    2.00    --  111.00-111.00  60.00   75
 37  ω    100.00 178.00   1.00    2.00    --  111.00 111.00 -60.00   78
 38  ω    100.00 178.00   1.00    2.00    --  111.00 111.00   0.00   78
 39  ω    100.00 178.00   1.00    2.00    --  111.00 111.00 150.00   78
 40  ω     43.00 128.00   1.00    2.00    --  111.00 -50.00-180.00   85
 41  ω     43.00 128.00   1.00    2.00    --  111.00 -50.00 -90.00   85
 42  ω     92.00 178.00   1.00    2.00    --  111.00  38.00-180.00   86
 43  ω     43.00 128.00   1.00    2.00    --  111.00 -54.00 118.23   85
 44  ω      4.00  33.00   1.00    1.00    --   36.95  89.00 144.60   29
 45  ω      3.00  32.00   1.00    1.00    --   36.95  90.00 -79.06   29
 46  ω    -32.00 106.00   1.00    1.00    --   36.95   0.00-180.00  138
 47  ω     20.00 104.00   1.00    1.00    --   36.95  57.00-120.00   84
 48  ω     10.00 105.00   1.00    1.00    --   36.95  77.00  30.00   95
 49  ω     20.00 104.00   1.00    1.00    --   36.95  57.00  90.00   84
;
_diffrn_measurement_method 'ω scans'
_symmetry_space_group_name_H-M 'P 21 21 21'
_symmetry_cell_setting orthorhombic
_space_group_IT_number 19
_space_group_crystal_system orthorhombic
#
# skip intenisty data and ins header
# finished with crysalis pro cif file
#
#------------------------------------------------------------------------
#
# data from SHELX
#
# skip first few lines
#
_chemical_formula_sum 
 'C13 H14 N2 O3' 
_chemical_formula_weight          246.26 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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' 
 'N'  'N'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
#
# already have cell_setting and H-M space group so skip
#
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
#
# skip some lines we already have
#
_exptl_crystal_density_diffrn     1.379 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              520 
_exptl_absorpt_coefficient_mu     0.821 
#
# skip some more
#
_reflns_number_total              2405 
_reflns_number_gt                 2393 
_reflns_threshold_expression      >2sigma(I) 
#
_computing_structure_solution     'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2015)' 
#
# add graphics and publication software to keep publcif happy
#
_computing_publication_material    'publCIF (Westrip, 2010)'
_computing_molecular_graphics      'SHELXLE (C. B. Hübschle et al.,2011)'
#
# rest of shelx cif file 
#
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0059(12) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    -0.01(14) 
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          2405 
_refine_ls_number_parameters      169 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0409 
_refine_ls_R_factor_gt            0.0408 
_refine_ls_wR_factor_ref          0.1196 
_refine_ls_wR_factor_gt           0.1194 
_refine_ls_goodness_of_fit_ref    1.191 
_refine_ls_restrained_S_all       1.191 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
 
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 
O1 O 0.49697(9) 0.10808(9) 0.18875(7) 0.0276(2) Uani 1 1 d . . . 
N1 N 0.97072(12) 0.48947(12) 0.11033(9) 0.0320(3) Uani 1 1 d . . . 
C1 C 1.03379(15) 0.56673(14) 0.18155(12) 0.0349(3) Uani 1 1 d . . . 
H1 H 1.1172 0.6190 0.1638 0.042 Uiso 1 1 calc R . . 
O2 O 0.41088(9) 0.27874(10) 0.08998(7) 0.0293(3) Uani 1 1 d . . . 
N2 N 0.76673(11) 0.33915(11) 0.07997(8) 0.0272(3) Uani 1 1 d . . . 
C2 C 0.98501(15) 0.57560(14) 0.28037(10) 0.0326(3) Uani 1 1 d . . . 
H2 H 1.0347 0.6330 0.3270 0.039 Uiso 1 1 calc R . . 
O3 O 0.64084(10) 0.18915(10) 0.37924(7) 0.0291(2) Uani 1 1 d . . . 
C3 C 0.86445(14) 0.50078(12) 0.31032(9) 0.0276(3) Uani 1 1 d . . . 
H3 H 0.8306 0.5050 0.3772 0.033 Uiso 1 1 calc R . . 
C4 C 0.79441(13) 0.41886(12) 0.23878(8) 0.0226(3) Uani 1 1 d . . . 
C5 C 0.85307(14) 0.42085(13) 0.14044(9) 0.0253(3) Uani 1 1 d . . . 
C6 C 0.67127(11) 0.32932(12) 0.23556(8) 0.0221(3) Uani 1 1 d . . . 
C7 C 0.66002(12) 0.28314(12) 0.13950(8) 0.0238(3) Uani 1 1 d . . . 
C8 C 0.53538(13) 0.19305(13) 0.10674(8) 0.0253(3) Uani 1 1 d . . . 
H8 H 0.5602 0.1361 0.0465 0.030 Uiso 1 1 calc R . . 
C9 C 0.44096(12) 0.20896(12) 0.25899(9) 0.0261(3) Uani 1 1 d . . . 
H9 H 0.3740 0.1634 0.3077 0.031 Uiso 1 1 calc R . . 
C10 C 0.56563(12) 0.28216(11) 0.31356(9) 0.0228(3) Uani 1 1 d . . . 
H10 H 0.5284 0.3645 0.3517 0.027 Uiso 1 1 calc R . . 
C11 C 0.35762(14) 0.31118(13) 0.18974(9) 0.0286(3) Uani 1 1 d . . . 
H11A H 0.2522 0.2953 0.1943 0.034 Uiso 1 1 calc R . . 
H11B H 0.3786 0.4095 0.2076 0.034 Uiso 1 1 calc R . . 
H22 H 0.7966(18) 0.3085(17) 0.0199(13) 0.029(4) Uiso 1 1 d . . . 
C12 C 0.58041(17) 0.17629(19) 0.47629(11) 0.0443(4) Uani 1 1 d . . . 
H12A H 0.4946 0.1146 0.4743 0.053 Uiso 1 1 calc R . . 
H12B H 0.5500 0.2691 0.5013 0.053 Uiso 1 1 calc R . . 
C13 C 0.69209(19) 0.1159(3) 0.54330(13) 0.0566(5) Uani 1 1 d . . . 
H13A H 0.7236 0.0254 0.5169 0.085 Uiso 1 1 calc R . . 
H13B H 0.6514 0.1030 0.6103 0.085 Uiso 1 1 calc R . . 
H13C H 0.7749 0.1795 0.5469 0.085 Uiso 1 1 calc R . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
O1 0.0296(5) 0.0180(4) 0.0352(4) -0.0031(3) 0.0022(3) -0.0030(3) 
N1 0.0273(5) 0.0319(6) 0.0368(6) 0.0016(4) 0.0056(4) -0.0032(4) 
C1 0.0250(6) 0.0306(6) 0.0491(7) 0.0018(6) 0.0037(6) -0.0069(5) 
O2 0.0268(5) 0.0294(5) 0.0316(5) -0.0048(3) -0.0047(3) 0.0015(3) 
N2 0.0258(5) 0.0292(6) 0.0265(5) -0.0021(4) 0.0029(4) -0.0019(4) 
C2 0.0281(6) 0.0270(6) 0.0427(7) -0.0041(5) -0.0064(5) -0.0033(5) 
O3 0.0318(4) 0.0292(4) 0.0263(4) 0.0050(3) 0.0042(3) 0.0057(4) 
C3 0.0269(6) 0.0249(6) 0.0309(6) -0.0041(4) -0.0036(5) 0.0005(4) 
C4 0.0215(6) 0.0203(5) 0.0260(5) 0.0013(4) 0.0009(4) 0.0029(4) 
C5 0.0240(6) 0.0237(5) 0.0283(5) 0.0012(4) 0.0023(4) 0.0004(5) 
C6 0.0198(5) 0.0201(5) 0.0265(5) -0.0006(4) 0.0004(4) 0.0014(4) 
C7 0.0218(5) 0.0221(5) 0.0275(5) 0.0009(4) 0.0008(4) 0.0003(4) 
C8 0.0236(6) 0.0230(5) 0.0293(5) -0.0031(4) -0.0020(4) -0.0015(4) 
C9 0.0233(5) 0.0222(5) 0.0328(6) -0.0033(4) 0.0034(4) -0.0006(4) 
C10 0.0221(5) 0.0190(5) 0.0274(5) 0.0006(4) 0.0035(4) 0.0005(4) 
C11 0.0227(5) 0.0285(6) 0.0347(6) -0.0062(5) -0.0033(5) -0.0003(5) 
C12 0.0455(8) 0.0547(9) 0.0327(7) 0.0087(6) 0.0102(6) 0.0100(7) 
C13 0.0434(8) 0.0861(13) 0.0403(7) 0.0251(8) -0.0046(7) -0.0091(9) 
 
_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_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C8 1.4115(14) . ? 
O1 C9 1.4438(14) . ? 
N1 C5 1.3344(16) . ? 
N1 C1 1.3403(19) . ? 
C1 C2 1.400(2) . ? 
C1 H1 0.9500 . ? 
O2 C8 1.4325(14) . ? 
O2 C11 1.4568(14) . ? 
N2 C7 1.3779(14) . ? 
N2 C5 1.3805(16) . ? 
N2 H22 0.900(17) . ? 
C2 C3 1.3856(19) . ? 
C2 H2 0.9500 . ? 
O3 C12 1.4198(16) . ? 
O3 C10 1.4318(14) . ? 
C3 C4 1.3972(17) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.4241(16) . ? 
C4 C6 1.4271(16) . ? 
C6 C7 1.3634(15) . ? 
C6 C10 1.5002(14) . ? 
C7 C8 1.5060(16) . ? 
C8 H8 1.0000 . ? 
C9 C10 1.5353(16) . ? 
C9 C11 1.5529(17) . ? 
C9 H9 1.0000 . ? 
C10 H10 1.0000 . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 C13 1.486(2) . ? 
C12 H12A 0.9900 . ? 
C12 H12B 0.9900 . ? 
C13 H13A 0.9800 . ? 
C13 H13B 0.9800 . ? 
C13 H13C 0.9800 . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C8 O1 C9 102.23(9) . . ? 
C5 N1 C1 114.35(12) . . ? 
N1 C1 C2 124.38(12) . . ? 
N1 C1 H1 117.8 . . ? 
C2 C1 H1 117.8 . . ? 
C8 O2 C11 104.53(9) . . ? 
C7 N2 C5 107.26(10) . . ? 
C7 N2 H22 127.6(10) . . ? 
C5 N2 H22 122.1(10) . . ? 
C3 C2 C1 120.13(12) . . ? 
C3 C2 H2 119.9 . . ? 
C1 C2 H2 119.9 . . ? 
C12 O3 C10 115.08(9) . . ? 
C2 C3 C4 117.76(12) . . ? 
C2 C3 H3 121.1 . . ? 
C4 C3 H3 121.1 . . ? 
C3 C4 C5 116.67(12) . . ? 
C3 C4 C6 136.77(11) . . ? 
C5 C4 C6 106.55(10) . . ? 
N1 C5 N2 125.07(11) . . ? 
N1 C5 C4 126.67(12) . . ? 
N2 C5 C4 108.26(11) . . ? 
C7 C6 C4 106.51(10) . . ? 
C7 C6 C10 120.59(10) . . ? 
C4 C6 C10 132.89(10) . . ? 
C6 C7 N2 111.37(10) . . ? 
C6 C7 C8 121.24(10) . . ? 
N2 C7 C8 127.15(10) . . ? 
O1 C8 O2 104.40(9) . . ? 
O1 C8 C7 107.24(9) . . ? 
O2 C8 C7 109.56(9) . . ? 
O1 C8 H8 111.8 . . ? 
O2 C8 H8 111.8 . . ? 
C7 C8 H8 111.8 . . ? 
O1 C9 C10 110.16(9) . . ? 
O1 C9 C11 102.19(10) . . ? 
C10 C9 C11 111.74(9) . . ? 
O1 C9 H9 110.8 . . ? 
C10 C9 H9 110.8 . . ? 
C11 C9 H9 110.8 . . ? 
O3 C10 C6 107.28(9) . . ? 
O3 C10 C9 111.98(9) . . ? 
C6 C10 C9 107.25(9) . . ? 
O3 C10 H10 110.1 . . ? 
C6 C10 H10 110.1 . . ? 
C9 C10 H10 110.1 . . ? 
O2 C11 C9 104.16(9) . . ? 
O2 C11 H11A 110.9 . . ? 
C9 C11 H11A 110.9 . . ? 
O2 C11 H11B 110.9 . . ? 
C9 C11 H11B 110.9 . . ? 
H11A C11 H11B 108.9 . . ? 
O3 C12 C13 108.15(12) . . ? 
O3 C12 H12A 110.1 . . ? 
C13 C12 H12A 110.1 . . ? 
O3 C12 H12B 110.1 . . ? 
C13 C12 H12B 110.1 . . ? 
H12A C12 H12B 108.4 . . ? 
C12 C13 H13A 109.5 . . ? 
C12 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C12 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
  
_refine_diff_density_max    0.272 
_refine_diff_density_min   -0.208 
_refine_diff_density_rms    0.049 
#
# end of shelx cif file
#
#--------0---------0---------0---------0---------0---------0---------0---------0
#
# add software references
#
_publ_section_references
;
Rigaku Oxford Diffraction (2015). CrysAlis PRO 1.171.38.43. Oxford
Diffraction Ltd, Abingdon, Oxfordshire, England.

Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). 'ShelXle: a Qt
graphical user interface for SHELXL' J. Appl. Cryst. 44, 1281-1284 .

Sheldrick, G. M. (2015). Acta Cryst. A71, 3--8.

Sheldrick, G. M. (2015). Acta Cryst. C71, 3--8.

Westrip, S. P. (2010). J. Appl. Cryst. 43, 920--925.
;
#
# other common references
# for list see iucr page at http://journals.iucr.org/e/services/stdswrefs.html
#SIR97
#Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., 
#Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999).
# J. Appl. Cryst. 32, 115-119.

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

#CRYSTALS
#Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin,
# D. J. (2003). J. Appl. Cryst. 36, 1487.

#SUPERFLIP
#Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.

#CrysAlis Pro
#Rigaku Oxford Diffraction (2015). CrysAlisPro 1.171.38.43. Oxford Diffraction 
#Ltd, Abingdon, Oxfordshire, England.

#SHELXT
#Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.

#SHELXL
#Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.

#PLATON
#Spek, A. L. (2009). Acta Cryst. D65, 148-155.

#PLATON SQUEEZE
#Spek, A. L. (2015). Acta Cryst. C71, 9-18.

#publCIF
#Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

#SHELXLE
# H\"bschle, C.B., Sheldrick, G.M. and Dittrich,B. (2011)
#'ShelXle: a Qt graphical user interface for SHELXL'
#J. Appl. Cryst. 44, 1281-1284 .
loop_
_publcif_info_cif.paper_type
 ?

