# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_002
_database_code_depnum_ccdc_archive 'CCDC 1858658'
loop_
_audit_author_name
_audit_author_address
'Zhenjie Su'
;Yangzhou University
China
;
_audit_update_record             
;
2018-07-27 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Cl N2 O'
_chemical_formula_sum            'C18 H13 Cl N2 O'
_chemical_formula_weight         308.75

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3411(18)
_cell_length_b                   7.109(2)
_cell_length_c                   16.557(5)
_cell_angle_alpha                93.165(9)
_cell_angle_beta                 92.574(9)
_cell_angle_gamma                92.317(10)
_cell_volume                     743.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    5375
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      27.15

_exptl_crystal_description       blocker
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11288
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3420
_reflns_number_gt                2482
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0562P)²+0.2564P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3353
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_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
Cl1 Cl 0.22275(12) 0.84406(10) 0.01443(4) 0.0788(3) Uani 1 1 d . . .
O1 O 0.02604(19) 0.15838(16) 0.39098(7) 0.0371(3) Uani 1 1 d . . .
C4 C 0.1372(3) 0.7270(3) 0.16129(12) 0.0429(4) Uani 1 1 d . . .
H4 H 0.2734 0.7724 0.1768 0.052 Uiso 1 1 calc R . .
C1 C -0.1192(3) 0.2573(2) 0.42969(10) 0.0341(4) Uani 1 1 d . . .
C5 C 0.0121(3) 0.6421(2) 0.21694(11) 0.0365(4) Uani 1 1 d . . .
N2 N -0.3568(3) 0.6990(3) 0.45181(12) 0.0595(5) Uani 1 1 d . . .
C2 C -0.1232(3) 0.4358(2) 0.40262(10) 0.0349(4) Uani 1 1 d . . .
C3 C -0.2533(3) 0.5795(3) 0.43014(11) 0.0402(4) Uani 1 1 d . . .
C6 C 0.1197(3) 0.2775(2) 0.33673(10) 0.0349(4) Uani 1 1 d . . .
C7 C 0.1015(3) 0.6233(2) 0.30203(11) 0.0395(4) Uani 1 1 d . . .
H7A H 0.2545 0.6288 0.3008 0.047 Uiso 1 1 calc R . .
H7B H 0.0616 0.7315 0.3353 0.047 Uiso 1 1 calc R . .
C8 C 0.2883(3) 0.1972(2) 0.29053(11) 0.0356(4) Uani 1 1 d . . .
C9 C -0.1902(3) 0.5792(3) 0.19263(12) 0.0459(5) Uani 1 1 d . . .
H9 H -0.2760 0.5221 0.2291 0.055 Uiso 1 1 calc R . .
C10 C 0.0349(3) 0.4481(2) 0.34248(10) 0.0340(4) Uani 1 1 d . . .
C11 C 0.4255(3) 0.0723(3) 0.32480(12) 0.0436(5) Uani 1 1 d . . .
H11 H 0.4054 0.0343 0.3768 0.052 Uiso 1 1 calc R . .
C12 C 0.0596(4) 0.7439(3) 0.08347(12) 0.0489(5) Uani 1 1 d . . .
C13 C 0.4827(4) 0.1754(3) 0.16952(14) 0.0581(6) Uani 1 1 d . . .
H13 H 0.5012 0.2092 0.1167 0.070 Uiso 1 1 calc R . .
C14 C 0.3167(3) 0.2442(3) 0.21140(12) 0.0493(5) Uani 1 1 d . . .
H14 H 0.2230 0.3227 0.1865 0.059 Uiso 1 1 calc R . .
C15 C -0.1418(4) 0.6819(3) 0.05915(13) 0.0577(6) Uani 1 1 d . . .
H15 H -0.1929 0.6948 0.0063 0.069 Uiso 1 1 calc R . .
C16 C 0.5905(3) 0.0049(3) 0.28224(14) 0.0513(5) Uani 1 1 d . . .
H16 H 0.6821 -0.0771 0.3060 0.062 Uiso 1 1 calc R . .
C17 C -0.2665(4) 0.6006(3) 0.11424(14) 0.0573(6) Uani 1 1 d . . .
H17 H -0.4041 0.5592 0.0987 0.069 Uiso 1 1 calc R . .
N1 N -0.2212(2) 0.1690(2) 0.48693(10) 0.0452(4) Uani 1 1 d . . .
H1A H -0.1922 0.0553 0.4971 0.054 Uiso 1 1 calc R . .
H1B H -0.3156 0.2260 0.5135 0.054 Uiso 1 1 calc R . .
C18 C 0.6212(4) 0.0574(3) 0.20496(15) 0.0559(6) Uani 1 1 d . . .
H18 H 0.7348 0.0135 0.1769 0.067 Uiso 1 1 calc R . .


_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
Cl1 C12 1.738(2) . ?
O1 C1 1.345(2) . ?
O1 C6 1.4027(19) . ?
C4 C12 1.372(3) . ?
C4 C5 1.389(2) . ?
C1 N1 1.341(2) . ?
C1 C2 1.370(2) . ?
C5 C9 1.376(3) . ?
C5 C7 1.510(3) . ?
N2 C3 1.146(2) . ?
C2 C3 1.408(2) . ?
C2 C10 1.448(2) . ?
C6 C10 1.347(2) . ?
C6 C8 1.459(2) . ?
C7 C10 1.502(2) . ?
C8 C14 1.388(3) . ?
C8 C11 1.393(3) . ?
C9 C17 1.383(3) . ?
C11 C16 1.375(3) . ?
C12 C15 1.370(3) . ?
C13 C18 1.374(3) . ?
C13 C14 1.378(3) . ?
C15 C17 1.370(3) . ?
C16 C18 1.373(3) . ?

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
C1 O1 C6 107.32(13) . . ?
C12 C4 C5 119.98(19) . . ?
N1 C1 O1 116.33(15) . . ?
N1 C1 C2 133.56(16) . . ?
O1 C1 C2 110.04(14) . . ?
C9 C5 C4 118.70(18) . . ?
C9 C5 C7 122.23(16) . . ?
C4 C5 C7 119.07(17) . . ?
C1 C2 C3 126.01(16) . . ?
C1 C2 C10 106.73(15) . . ?
C3 C2 C10 127.24(16) . . ?
N2 C3 C2 178.6(2) . . ?
C10 C6 O1 109.91(14) . . ?
C10 C6 C8 134.37(16) . . ?
O1 C6 C8 115.65(14) . . ?
C10 C7 C5 116.40(15) . . ?
C14 C8 C11 118.30(17) . . ?
C14 C8 C6 120.75(16) . . ?
C11 C8 C6 120.94(16) . . ?
C5 C9 C17 120.36(19) . . ?
C6 C10 C2 106.00(15) . . ?
C6 C10 C7 128.05(16) . . ?
C2 C10 C7 125.69(16) . . ?
C16 C11 C8 120.50(19) . . ?
C15 C12 C4 121.45(19) . . ?
C15 C12 Cl1 119.67(17) . . ?
C4 C12 Cl1 118.88(18) . . ?
C18 C13 C14 120.6(2) . . ?
C13 C14 C8 120.44(19) . . ?
C12 C15 C17 118.7(2) . . ?
C18 C16 C11 120.64(19) . . ?
C15 C17 C9 120.8(2) . . ?
C16 C18 C13 119.39(19) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.045
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_001_a
_database_code_depnum_ccdc_archive 'CCDC 1880678'
loop_
_audit_author_name
_audit_author_address
'Zhenjie Su' 'Yangzhou University'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 Br N2 O S'
_chemical_formula_sum            'C16 H11 Br N2 O S'
_chemical_formula_weight         359.23

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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Triclinic'
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.73(1)
_cell_length_b                   10.20(2)
_cell_length_c                   16.80(2)
_cell_angle_alpha                77.0(1)
_cell_angle_beta                 86.0(1)
_cell_angle_gamma                77.3(1)
_cell_volume                     770(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    2908
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      22.22

_exptl_crystal_description       blocker
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    2.804
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7961
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11664
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0968
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.24
_diffrn_reflns_theta_max         27.43
_reflns_number_total             3502
_reflns_number_gt                1755
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1371P)²+0.9928P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3436
_refine_ls_number_parameters     190
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1723
_refine_ls_R_factor_gt           0.0803
_refine_ls_wR_factor_ref         0.2648
_refine_ls_wR_factor_gt          0.2162
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_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
Br01 Br -0.4343(2) 0.71966(9) 0.55619(5) 0.0729(5) Uani 1 1 d . . .
S1 S 0.7639(6) 0.4502(3) 0.26320(17) 0.0836(8) Uani 1 1 d U . .
C14 C 0.8004(11) 0.4758(5) 0.1011(3) 0.0158(10) Uani 1 1 d U . .
H14 H 0.7638 0.5008 0.0456 0.019 Uiso 1 1 calc R . .
O1 O 0.4451(10) 0.9687(5) 0.2425(3) 0.0459(12) Uani 1 1 d . . .
N1 N 0.7301(15) 1.0936(6) 0.1548(4) 0.0589(18) Uani 1 1 d . . .
H1A H 0.8359 1.1087 0.1115 0.071 Uiso 1 1 calc R . .
H1B H 0.7024 1.1493 0.1875 0.071 Uiso 1 1 calc R . .
N2 N 0.8657(17) 0.8525(7) -0.0041(4) 0.0643(19) Uani 1 1 d . . .
C8 C 0.4295(14) 0.7901(7) 0.1822(4) 0.0385(16) Uani 1 1 d . . .
C9 C 0.6100(15) 0.8783(7) 0.1333(4) 0.0415(16) Uani 1 1 d . . .
C7 C 0.3359(15) 0.8467(7) 0.2488(4) 0.0417(16) Uani 1 1 d . . .
C13 C 0.6295(14) 0.5401(7) 0.1703(4) 0.0402(15) Uani 1 1 d U . .
C11 C 0.7523(16) 0.8628(7) 0.0563(5) 0.0441(17) Uani 1 1 d . . .
C10 C 0.6109(14) 0.9855(7) 0.1712(4) 0.0397(16) Uani 1 1 d . . .
C6 C 0.1519(15) 0.8180(7) 0.3207(4) 0.0420(16) Uani 1 1 d . . .
C12 C 0.3749(16) 0.6634(7) 0.1576(4) 0.0448(17) Uani 1 1 d . . .
H12A H 0.3252 0.6879 0.1005 0.054 Uiso 1 1 calc R . .
H12B H 0.2090 0.6361 0.1887 0.054 Uiso 1 1 calc R . .
C5 C 0.0333(17) 0.9191(8) 0.3668(4) 0.0501(19) Uani 1 1 d . . .
H5 H 0.0747 1.0065 0.3507 0.060 Uiso 1 1 calc R . .
C2 C -0.0971(18) 0.6593(8) 0.4156(5) 0.057(2) Uani 1 1 d . . .
H2 H -0.1462 0.5735 0.4315 0.068 Uiso 1 1 calc R . .
C4 C -0.1390(18) 0.8910(8) 0.4337(5) 0.060(2) Uani 1 1 d . . .
H4 H -0.2148 0.9593 0.4624 0.071 Uiso 1 1 calc R . .
C1 C 0.0816(18) 0.6869(8) 0.3479(5) 0.053(2) Uani 1 1 d . . .
H1 H 0.1571 0.6178 0.3198 0.064 Uiso 1 1 calc R . .
C3 C -0.2027(16) 0.7612(8) 0.4596(4) 0.0484(18) Uani 1 1 d . . .
C15 C 1.0340(19) 0.3662(9) 0.1433(6) 0.065(2) Uani 1 1 d U . .
H15 H 1.1752 0.3152 0.1147 0.079 Uiso 1 1 calc R . .
C16 C 1.033(2) 0.3438(9) 0.2246(8) 0.082(3) Uani 1 1 d . . .
H16 H 1.1680 0.2759 0.2567 0.098 Uiso 1 1 calc R . .


_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
Br01 C3 1.913(8) . ?
S1 C16 1.68(3) . ?
S1 C13 1.709(8) . ?
C14 C15 1.48(3) . ?
C14 C13 1.554(9) . ?
C14 H14 0.9300 . ?
O1 C10 1.384(9) . ?
O1 C7 1.429(9) . ?
N1 C10 1.31(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C11 1.13(3) . ?
C8 C7 1.38(3) . ?
C8 C9 1.46(3) . ?
C8 C12 1.520(11) . ?
C9 C10 1.38(3) . ?
C9 C11 1.44(3) . ?
C7 C6 1.46(3) . ?
C13 C12 1.52(3) . ?
C6 C1 1.417(11) . ?
C6 C5 1.42(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C5 C4 1.36(3) . ?
C5 H5 0.9300 . ?
C2 C1 1.39(3) . ?
C2 C3 1.39(3) . ?
C2 H2 0.9300 . ?
C4 C3 1.390(12) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C15 C16 1.34(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
C16 S1 C13 94.9(5) . . ?
C15 C14 C13 104.7(5) . . ?
C15 C14 H14 127.7 . . ?
C13 C14 H14 127.7 . . ?
C10 O1 C7 107.3(10) . . ?
C10 N1 H1A 120.0 . . ?
C10 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C7 C8 C9 105.8(6) . . ?
C7 C8 C12 131.6(9) . . ?
C9 C8 C12 122.6(6) . . ?
C10 C9 C11 125.0(11) . . ?
C10 C9 C8 108.4(6) . . ?
C11 C9 C8 126.7(12) . . ?
C8 C7 O1 109.6(12) . . ?
C8 C7 C6 137.3(13) . . ?
O1 C7 C6 113.1(10) . . ?
C12 C13 C14 125.2(5) . . ?
C12 C13 S1 124.7(9) . . ?
C14 C13 S1 110.0(5) . . ?
N2 C11 C9 178.8(8) . . ?
N1 C10 C9 134.9(14) . . ?
N1 C10 O1 116.2(10) . . ?
C9 C10 O1 108.9(6) . . ?
C1 C6 C5 116.9(7) . . ?
C1 C6 C7 121.1(8) . . ?
C5 C6 C7 122.0(7) . . ?
C8 C12 C13 114.8(6) . . ?
C8 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
C8 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C4 C5 C6 121.4(7) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C2 C3 119.4(15) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C5 C4 C3 120.6(9) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C2 C1 C6 121.5(9) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C4 C3 C2 120.3(7) . . ?
C4 C3 Br01 120.5(8) . . ?
C2 C3 Br01 119.2(6) . . ?
C16 C15 C14 116.9(11) . . ?
C16 C15 H15 121.6 . . ?
C14 C15 H15 121.6 . . ?
C15 C16 S1 113.4(12) . . ?
C15 C16 H16 123.3 . . ?
S1 C16 H16 123.3 . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        27.43
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         1.353
_refine_diff_density_min         -0.896
_refine_diff_density_rms         0.134
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_001_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1908517'
loop_
_audit_author_name
_audit_author_address
'Zhenjie Su' 'Yangzhou University'
_audit_update_record             
;
2019-04-08 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Br N2 O'
_chemical_formula_sum            'C18 H13 Br N2 O'
_chemical_formula_weight         353.20

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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic'
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.192(5)
_cell_length_b                   7.311(2)
_cell_length_c                   16.718(3)
_cell_angle_alpha                87.67(2)
_cell_angle_beta                 85.16(3)
_cell_angle_gamma                86.34(2)
_cell_volume                     752.1(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    5046
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.31

_exptl_crystal_description       blocker
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    2.736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9835
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.22
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2646
_reflns_number_gt                2114
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0474P)²+5.1536P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2632
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.1831
_refine_ls_wR_factor_gt          0.1719
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_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
Br1 Br 0.31506(19) 0.25165(12) 0.47961(5) 0.0786(4) Uani 1 1 d . . .
C3 C 0.4278(13) 0.3027(9) 0.5770(4) 0.0497(17) Uani 1 1 d . . .
C2 C 0.6336(13) 0.2348(9) 0.5927(4) 0.0502(18) Uani 1 1 d . . .
H2 H 0.7193 0.1676 0.5546 0.060 Uiso 1 1 calc R . .
C1 C 0.7104(11) 0.2669(9) 0.6646(4) 0.0444(16) Uani 1 1 d . . .
H1 H 0.8486 0.2201 0.6754 0.053 Uiso 1 1 calc R . .
C6 C 0.5872(10) 0.3673(8) 0.7215(4) 0.0356(13) Uani 1 1 d . . .
C7 C 0.6747(11) 0.3942(8) 0.8009(4) 0.0406(14) Uani 1 1 d . . .
H7A H 0.6434 0.2883 0.8358 0.049 Uiso 1 1 calc R . .
H7B H 0.8314 0.3973 0.7924 0.049 Uiso 1 1 calc R . .
C8 C 0.5893(9) 0.5624(8) 0.8434(4) 0.0362(13) Uani 1 1 d . . .
C9 C 0.6721(9) 0.7284(8) 0.8390(3) 0.0316(12) Uani 1 1 d . . .
C10 C 0.8533(10) 0.8102(8) 0.7927(4) 0.0364(13) Uani 1 1 d . . .
C11 C 0.9824(11) 0.9294(9) 0.8262(4) 0.0453(16) Uani 1 1 d . . .
H11 H 0.9486 0.9630 0.8790 0.054 Uiso 1 1 calc R . .
C12 C 1.1579(12) 0.9988(10) 0.7835(5) 0.0538(18) Uani 1 1 d . . .
H12 H 1.2412 1.0797 0.8072 0.065 Uiso 1 1 calc R . .
C13 C 1.2108(11) 0.9507(9) 0.7072(5) 0.0536(19) Uani 1 1 d . . .
H13 H 1.3336 0.9948 0.6788 0.064 Uiso 1 1 calc R . .
C5 C 0.3809(11) 0.4360(9) 0.7036(4) 0.0446(15) Uani 1 1 d . . .
H5 H 0.2954 0.5050 0.7411 0.054 Uiso 1 1 calc R . .
C4 C 0.3015(12) 0.4038(9) 0.6315(4) 0.0487(17) Uani 1 1 d . . .
H4 H 0.1637 0.4505 0.6201 0.058 Uiso 1 1 calc R . .
C17 C 0.4090(10) 0.5711(9) 0.9035(4) 0.0375(14) Uani 1 1 d . . .
C18 C 0.4009(10) 0.7424(9) 0.9326(4) 0.0387(14) Uani 1 1 d . . .
O1 O 0.5574(7) 0.8416(6) 0.8951(2) 0.0391(10) Uani 1 1 d . . .
C15 C 0.9057(11) 0.7664(9) 0.7144(4) 0.0443(16) Uani 1 1 d . . .
H15 H 0.8198 0.6885 0.6901 0.053 Uiso 1 1 calc R . .
C14 C 1.0818(12) 0.8350(9) 0.6709(4) 0.0510(17) Uani 1 1 d . . .
H14 H 1.1149 0.8044 0.6176 0.061 Uiso 1 1 calc R . .
N2 N 0.2759(9) 0.8282(8) 0.9903(3) 0.0511(15) Uani 1 1 d . . .
H2A H 0.2987 0.9391 1.0011 0.061 Uiso 1 1 calc R . .
H2B H 0.1727 0.7726 1.0167 0.061 Uiso 1 1 calc R . .
C16 C 0.2723(11) 0.4288(9) 0.9298(4) 0.0426(15) Uani 1 1 d . . .
N1 N 0.1643(11) 0.3120(9) 0.9496(4) 0.0648(18) Uani 1 1 d . . .


_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
Br1 C3 1.885(10) . ?
C3 C4 1.359(11) . ?
C3 C2 1.380(12) . ?
C2 C1 1.363(11) . ?
C2 H2 0.9300 . ?
C1 C6 1.373(10) . ?
C1 H1 0.9300 . ?
C6 C5 1.394(11) . ?
C6 C7 1.500(10) . ?
C7 C8 1.490(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.344(10) . ?
C8 C17 1.438(10) . ?
C9 O1 1.394(8) . ?
C9 C10 1.455(10) . ?
C10 C15 1.367(10) . ?
C10 C11 1.385(10) . ?
C11 C12 1.362(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.344(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(12) . ?
C13 H13 0.9300 . ?
C5 C4 1.374(11) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C17 C18 1.358(10) . ?
C17 C16 1.416(10) . ?
C18 N2 1.336(9) . ?
C18 O1 1.344(8) . ?
C15 C14 1.369(11) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C16 N1 1.139(9) . ?

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
C4 C3 C2 121.1(7) . . ?
C4 C3 Br1 118.8(7) . . ?
C2 C3 Br1 120.0(6) . . ?
C1 C2 C3 119.5(6) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C1 C6 121.1(7) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C6 C5 118.1(6) . . ?
C1 C6 C7 119.5(6) . . ?
C5 C6 C7 122.4(6) . . ?
C8 C7 C6 116.0(6) . . ?
C8 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C9 C8 C17 106.6(6) . . ?
C9 C8 C7 128.0(6) . . ?
C17 C8 C7 125.1(6) . . ?
C8 C9 O1 109.8(6) . . ?
C8 C9 C10 135.0(6) . . ?
O1 C9 C10 115.2(6) . . ?
C15 C10 C11 117.6(6) . . ?
C15 C10 C9 120.5(6) . . ?
C11 C10 C9 121.9(6) . . ?
C12 C11 C10 121.5(7) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 120.2(7) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.9(7) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C4 C5 C6 121.3(6) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C3 C4 C5 118.8(7) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C18 C17 C16 126.6(6) . . ?
C18 C17 C8 106.0(6) . . ?
C16 C17 C8 127.4(6) . . ?
N2 C18 O1 115.2(6) . . ?
N2 C18 C17 133.8(6) . . ?
O1 C18 C17 111.0(6) . . ?
C18 O1 C9 106.6(5) . . ?
C10 C15 C14 121.4(7) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C14 C13 119.3(7) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C18 N2 H2A 120.0 . . ?
C18 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C16 C17 178.5(7) . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C3 C2 C1 1.1(10) . . . . ?
Br1 C3 C2 C1 -177.6(5) . . . . ?
C3 C2 C1 C6 -0.6(10) . . . . ?
C2 C1 C6 C5 -0.1(9) . . . . ?
C2 C1 C6 C7 178.0(6) . . . . ?
C1 C6 C7 C8 153.7(6) . . . . ?
C5 C6 C7 C8 -28.3(9) . . . . ?
C6 C7 C8 C9 -91.7(9) . . . . ?
C6 C7 C8 C17 94.3(8) . . . . ?
C17 C8 C9 O1 1.7(7) . . . . ?
C7 C8 C9 O1 -173.2(6) . . . . ?
C17 C8 C9 C10 178.8(7) . . . . ?
C7 C8 C9 C10 3.9(12) . . . . ?
C8 C9 C10 C15 37.1(11) . . . . ?
O1 C9 C10 C15 -145.9(6) . . . . ?
C8 C9 C10 C11 -140.9(8) . . . . ?
O1 C9 C10 C11 36.2(8) . . . . ?
C15 C10 C11 C12 -1.1(10) . . . . ?
C9 C10 C11 C12 176.9(6) . . . . ?
C10 C11 C12 C13 -0.6(11) . . . . ?
C11 C12 C13 C14 2.3(11) . . . . ?
C1 C6 C5 C4 0.4(9) . . . . ?
C7 C6 C5 C4 -177.6(6) . . . . ?
C2 C3 C4 C5 -0.9(11) . . . . ?
Br1 C3 C4 C5 177.9(5) . . . . ?
C6 C5 C4 C3 0.1(10) . . . . ?
C9 C8 C17 C18 -1.6(7) . . . . ?
C7 C8 C17 C18 173.5(6) . . . . ?
C9 C8 C17 C16 -179.4(6) . . . . ?
C7 C8 C17 C16 -4.3(10) . . . . ?
C16 C17 C18 N2 0.5(13) . . . . ?
C8 C17 C18 N2 -177.3(7) . . . . ?
C16 C17 C18 O1 178.7(6) . . . . ?
C8 C17 C18 O1 1.0(7) . . . . ?
N2 C18 O1 C9 178.6(5) . . . . ?
C17 C18 O1 C9 0.0(7) . . . . ?
C8 C9 O1 C18 -1.1(7) . . . . ?
C10 C9 O1 C18 -178.9(5) . . . . ?
C11 C10 C15 C14 1.2(10) . . . . ?
C9 C10 C15 C14 -176.8(6) . . . . ?
C10 C15 C14 C13 0.3(10) . . . . ?
C12 C13 C14 C15 -2.1(11) . . . . ?
C18 C17 C16 N1 175(100) . . . . ?
C8 C17 C16 N1 -8(34) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.595
_refine_diff_density_rms         0.096
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_001_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1908518'
loop_
_audit_author_name
_audit_author_address
'Zhenjie Su' 'Yangzhou University'
_audit_update_record             
;
2019-04-08 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 Br Cl2 N2 O'
_chemical_formula_sum            'C18 H11 Br Cl2 N2 O'
_chemical_formula_weight         422.09

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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic'
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.722(5)
_cell_length_b                   9.677(6)
_cell_length_c                   11.637(8)
_cell_angle_alpha                101.028(14)
_cell_angle_beta                 103.348(17)
_cell_angle_gamma                112.332(11)
_cell_volume                     840.4(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    298
_cell_measurement_reflns_used    7027
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      26.95

_exptl_crystal_description       blocker
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    2.770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13120
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         27.63
_reflns_number_total             3910
_reflns_number_gt                3130
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0381P)²+0.3614P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3873
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_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
Br1 Br 0.84317(4) -0.03464(3) 0.73135(3) 0.06695(12) Uani 1 1 d . . .
Cl1 Cl 0.41106(9) 0.64442(8) 0.55185(6) 0.0668(2) Uani 1 1 d . . .
Cl2 Cl -0.20183(10) 0.17569(10) 0.24266(6) 0.0788(2) Uani 1 1 d . . .
O1 O 0.3412(2) 0.24591(18) 0.96691(13) 0.0453(4) Uani 1 1 d . . .
N1 N 0.1598(3) 0.2841(3) 1.0687(2) 0.0630(6) Uani 1 1 d . . .
H1A H 0.1824 0.2273 1.1123 0.076 Uiso 1 1 calc R . .
H1B H 0.0897 0.3236 1.0813 0.076 Uiso 1 1 calc R . .
C6 C 0.2283(3) 0.3922(2) 0.61375(18) 0.0368(4) Uani 1 1 d . . .
C1 C 0.2333(3) 0.4657(2) 0.52282(19) 0.0402(5) Uani 1 1 d . . .
C8 C 0.3358(3) 0.3818(2) 0.83113(18) 0.0406(5) Uani 1 1 d . . .
N2 N 0.0142(3) 0.5204(3) 0.8645(2) 0.0621(6) Uani 1 1 d . . .
C5 C 0.0850(3) 0.2490(3) 0.5848(2) 0.0471(5) Uani 1 1 d . . .
H5 H 0.0778 0.1960 0.6436 0.056 Uiso 1 1 calc R . .
C7 C 0.3721(3) 0.4662(3) 0.73849(19) 0.0435(5) Uani 1 1 d . . .
H7A H 0.4803 0.4710 0.7267 0.052 Uiso 1 1 calc R . .
H7B H 0.3905 0.5732 0.7722 0.052 Uiso 1 1 calc R . .
C16 C 0.2334(3) 0.3107(3) 0.9820(2) 0.0449(5) Uani 1 1 d . . .
C17 C 0.2217(3) 0.3942(3) 0.90029(19) 0.0426(5) Uani 1 1 d . . .
C9 C 0.4033(3) 0.2885(3) 0.87160(18) 0.0424(5) Uani 1 1 d . . .
C10 C 0.5147(3) 0.2198(3) 0.83998(19) 0.0424(5) Uani 1 1 d . . .
C3 C -0.0361(3) 0.2608(3) 0.38568(19) 0.0461(5) Uani 1 1 d . . .
C13 C 0.7130(3) 0.0720(3) 0.7769(2) 0.0496(5) Uani 1 1 d . . .
C18 C 0.1090(3) 0.4655(3) 0.8820(2) 0.0461(5) Uani 1 1 d . . .
C2 C 0.1030(3) 0.4021(3) 0.4089(2) 0.0477(5) Uani 1 1 d . . .
H2 H 0.1094 0.4539 0.3493 0.057 Uiso 1 1 calc R . .
C14 C 0.6934(3) 0.0874(3) 0.8908(2) 0.0511(6) Uani 1 1 d . . .
H14 H 0.7460 0.0483 0.9467 0.061 Uiso 1 1 calc R . .
C4 C -0.0469(3) 0.1828(3) 0.4721(2) 0.0506(6) Uani 1 1 d . . .
H4 H -0.1424 0.0863 0.4546 0.061 Uiso 1 1 calc R . .
C15 C 0.5955(3) 0.1609(3) 0.9223(2) 0.0476(5) Uani 1 1 d . . .
H15 H 0.5827 0.1717 1.0003 0.057 Uiso 1 1 calc R . .
C11 C 0.5379(3) 0.2021(3) 0.7246(2) 0.0549(6) Uani 1 1 d . . .
H11 H 0.4852 0.2400 0.6677 0.066 Uiso 1 1 calc R . .
C12 C 0.6372(4) 0.1297(3) 0.6933(2) 0.0592(6) Uani 1 1 d . . .
H12 H 0.6530 0.1197 0.6163 0.071 Uiso 1 1 calc R . .


_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
Br1 C13 1.896(3) . ?
Cl1 C1 1.734(2) . ?
Cl2 C3 1.731(2) . ?
O1 C16 1.338(3) . ?
O1 C9 1.406(3) . ?
N1 C16 1.331(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C6 C5 1.381(3) . ?
C6 C1 1.383(3) . ?
C6 C7 1.507(3) . ?
C1 C2 1.374(3) . ?
C8 C9 1.350(3) . ?
C8 C17 1.441(3) . ?
C8 C7 1.492(3) . ?
N2 C18 1.142(3) . ?
C5 C4 1.370(3) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C16 C17 1.370(3) . ?
C17 C18 1.401(3) . ?
C9 C10 1.443(3) . ?
C10 C11 1.392(3) . ?
C10 C15 1.394(3) . ?
C3 C2 1.364(3) . ?
C3 C4 1.367(3) . ?
C13 C14 1.362(4) . ?
C13 C12 1.373(4) . ?
C2 H2 0.9300 . ?
C14 C15 1.369(3) . ?
C14 H14 0.9300 . ?
C4 H4 0.9300 . ?
C15 H15 0.9300 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

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
C16 O1 C9 107.68(16) . . ?
C16 N1 H1A 120.0 . . ?
C16 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C5 C6 C1 116.74(19) . . ?
C5 C6 C7 121.94(18) . . ?
C1 C6 C7 121.32(18) . . ?
C2 C1 C6 122.6(2) . . ?
C2 C1 Cl1 118.14(16) . . ?
C6 C1 Cl1 119.25(16) . . ?
C9 C8 C17 106.63(19) . . ?
C9 C8 C7 129.5(2) . . ?
C17 C8 C7 123.8(2) . . ?
C4 C5 C6 121.9(2) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C8 C7 C6 114.48(18) . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N1 C16 O1 117.15(19) . . ?
N1 C16 C17 132.6(2) . . ?
O1 C16 C17 110.2(2) . . ?
C16 C17 C18 125.9(2) . . ?
C16 C17 C8 106.4(2) . . ?
C18 C17 C8 127.50(19) . . ?
C8 C9 O1 109.0(2) . . ?
C8 C9 C10 136.8(2) . . ?
O1 C9 C10 114.10(18) . . ?
C11 C10 C15 117.6(2) . . ?
C11 C10 C9 121.69(19) . . ?
C15 C10 C9 120.7(2) . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 Cl2 119.54(17) . . ?
C4 C3 Cl2 118.85(18) . . ?
C14 C13 C12 121.2(2) . . ?
C14 C13 Br1 119.55(18) . . ?
C12 C13 Br1 119.24(19) . . ?
N2 C18 C17 178.2(3) . . ?
C3 C2 C1 118.12(19) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C14 C15 C10 121.3(2) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 119.3(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.63
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.049
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_002_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1893325'
loop_
_audit_author_name
_audit_author_address
'Zhenjie Su' 'Yangzhou University'
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 N2 O3'
_chemical_formula_sum            'C20 H14 N2 O3'
_chemical_formula_weight         330.33

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.542(4)
_cell_length_b                   12.009(4)
_cell_length_c                   14.738(5)
_cell_angle_alpha                100.009(11)
_cell_angle_beta                 105.015(10)
_cell_angle_gamma                117.020(10)
_cell_volume                     1653.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7375
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.57

_exptl_crystal_description       blocker
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20658
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0858
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         27.66
_reflns_number_total             7716
_reflns_number_gt                4187
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1635P)²+1.2962P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7426
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.1032
_refine_ls_wR_factor_ref         0.3322
_refine_ls_wR_factor_gt          0.2930
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_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
C32 C 0.6224(4) 0.1748(4) 0.4100(3) 0.0474(9) Uani 1 1 d . . .
H32 H 0.7102 0.1841 0.4351 0.057 Uiso 1 1 calc R . .
O2 O -0.4289(3) 0.6450(3) 0.1196(3) 0.0714(9) Uani 1 1 d . . .
C12 C -0.2250(4) 0.7208(4) 0.0844(3) 0.0485(9) Uani 1 1 d . . .
H12 H -0.2428 0.7820 0.0631 0.058 Uiso 1 1 calc R . .
O3 O -0.3700(3) 0.4671(3) 0.1958(2) 0.0727(9) Uani 1 1 d . . .
O6 O 0.2501(3) -0.0872(3) 0.2946(2) 0.0693(9) Uani 1 1 d . . .
O1 O 0.2050(3) 1.0381(3) 0.0320(3) 0.0774(10) Uani 1 1 d . . .
C13 C -0.3135(4) 0.6369(4) 0.1198(3) 0.0504(9) Uani 1 1 d . . .
C10 C -0.0197(4) 0.8064(4) 0.0372(3) 0.0495(9) Uani 1 1 d . . .
H10 H -0.0193 0.8895 0.0471 0.059 Uiso 1 1 calc R . .
C31 C 0.6147(4) 0.2869(4) 0.4096(3) 0.0449(8) Uani 1 1 d . . .
C11 C -0.1084(4) 0.7161(4) 0.0796(3) 0.0475(9) Uani 1 1 d . . .
O5 O 0.5195(3) -0.0535(3) 0.3784(3) 0.0750(9) Uani 1 1 d . . .
C34 C 0.3710(4) 0.0346(4) 0.3336(3) 0.0516(9) Uani 1 1 d . . .
C30 C 0.7477(4) 0.4166(4) 0.4519(3) 0.0469(9) Uani 1 1 d . . .
H30 H 0.8283 0.4122 0.4460 0.056 Uiso 1 1 calc R . .
O4 O 0.9856(3) 0.6414(4) 0.4488(3) 0.0876(11) Uani 1 1 d . . .
C33 C 0.5035(4) 0.0513(4) 0.3742(3) 0.0510(9) Uani 1 1 d . . .
C14 C -0.2864(4) 0.5487(4) 0.1564(3) 0.0559(10) Uani 1 1 d . . .
C29 C 0.7841(4) 0.5174(4) 0.5510(3) 0.0491(9) Uani 1 1 d . . .
C9 C -0.0172(4) 0.7526(4) -0.0645(3) 0.0503(9) Uani 1 1 d . . .
C40 C 0.6755(4) 0.4923(4) 0.5910(3) 0.0537(9) Uani 1 1 d . . .
C27 C 0.8811(4) 0.6485(4) 0.4391(3) 0.0541(10) Uani 1 1 d . . .
C6 C 0.3781(4) 0.9861(4) 0.0900(3) 0.0510(9) Uani 1 1 d . . .
C35 C 0.3631(4) 0.1448(4) 0.3316(3) 0.0590(11) Uani 1 1 d . . .
H35 H 0.2753 0.1349 0.3043 0.071 Uiso 1 1 calc R . .
C36 C 0.4817(4) 0.2689(4) 0.3690(3) 0.0549(10) Uani 1 1 d . . .
H36 H 0.4735 0.3421 0.3673 0.066 Uiso 1 1 calc R . .
C26 C 0.8703(4) 0.7573(4) 0.4139(3) 0.0539(10) Uani 1 1 d . . .
C28 C 0.7574(4) 0.5435(4) 0.4510(3) 0.0513(9) Uani 1 1 d . . .
H28 H 0.6677 0.5379 0.4212 0.062 Uiso 1 1 calc R . .
C19 C -0.0277(5) 0.8191(5) -0.1365(3) 0.0633(11) Uani 1 1 d . . .
C7 C 0.2317(4) 0.9549(4) 0.0495(3) 0.0538(10) Uani 1 1 d . . .
C15 C -0.1696(5) 0.5453(4) 0.1532(4) 0.0647(11) Uani 1 1 d . . .
H15 H -0.1502 0.4861 0.1766 0.078 Uiso 1 1 calc R . .
C20 C -0.0851(5) 0.6112(5) -0.1090(3) 0.0612(11) Uani 1 1 d . . .
C8 C 0.1133(4) 0.8209(4) 0.0329(3) 0.0524(10) Uani 1 1 d . . .
H8 H 0.1402 0.7623 0.0583 0.063 Uiso 1 1 calc R . .
N4 N 0.5883(4) 0.4692(4) 0.6193(3) 0.0739(11) Uani 1 1 d . . .
C1 C 0.4847(4) 1.1173(5) 0.1321(3) 0.0630(11) Uani 1 1 d . . .
H1 H 0.4626 1.1828 0.1334 0.076 Uiso 1 1 calc R . .
C16 C -0.0817(5) 0.6278(4) 0.1158(3) 0.0627(11) Uani 1 1 d . . .
H16 H -0.0031 0.6244 0.1149 0.075 Uiso 1 1 calc R . .
C39 C 0.9247(5) 0.5861(4) 0.6262(3) 0.0639(11) Uani 1 1 d . . .
C5 C 0.4104(5) 0.8889(5) 0.0859(4) 0.0676(12) Uani 1 1 d . . .
H5 H 0.3394 0.7996 0.0571 0.081 Uiso 1 1 calc R . .
N1 N -0.0408(5) 0.8676(5) -0.1949(4) 0.0935(14) Uani 1 1 d . . .
C17 C -0.4968(5) 0.5786(6) 0.1800(4) 0.0802(14) Uani 1 1 d . . .
H17A H -0.5908 0.5642 0.1611 0.096 Uiso 1 1 calc R . .
H17B H -0.4438 0.6344 0.2497 0.096 Uiso 1 1 calc R . .
N3 N 1.0329(5) 0.6388(5) 0.6859(4) 0.1008(16) Uani 1 1 d . . .
C2 C 0.6242(5) 1.1538(6) 0.1725(4) 0.0794(15) Uani 1 1 d . . .
H2 H 0.6954 1.2430 0.2016 0.095 Uiso 1 1 calc R . .
C3 C 0.6555(5) 1.0580(6) 0.1690(4) 0.0816(15) Uani 1 1 d . . .
H3 H 0.7492 1.0822 0.1967 0.098 Uiso 1 1 calc R . .
C21 C 0.9501(6) 0.8257(5) 0.3651(4) 0.0789(14) Uani 1 1 d . . .
H21 H 1.0106 0.8029 0.3482 0.095 Uiso 1 1 calc R . .
C25 C 0.7832(5) 0.7937(5) 0.4410(4) 0.0781(14) Uani 1 1 d . . .
H25 H 0.7287 0.7481 0.4736 0.094 Uiso 1 1 calc R . .
C38 C 0.2699(5) -0.1822(5) 0.3317(4) 0.0790(14) Uani 1 1 d . . .
H38A H 0.1878 -0.2704 0.2938 0.095 Uiso 1 1 calc R . .
H38B H 0.2799 -0.1631 0.4010 0.095 Uiso 1 1 calc R . .
C18 C -0.5058(5) 0.4509(5) 0.1671(4) 0.0802(15) Uani 1 1 d . . .
H18A H -0.5536 0.4072 0.2072 0.096 Uiso 1 1 calc R . .
H18B H -0.5611 0.3944 0.0977 0.096 Uiso 1 1 calc R . .
C37 C 0.3952(6) -0.1788(5) 0.3242(5) 0.0812(15) Uani 1 1 d . . .
H37A H 0.4052 -0.2451 0.3488 0.097 Uiso 1 1 calc R . .
H37B H 0.3828 -0.2018 0.2545 0.097 Uiso 1 1 calc R . .
N2 N -0.1407(5) 0.4993(5) -0.1421(4) 0.0874(13) Uani 1 1 d . . .
C4 C 0.5533(6) 0.9270(6) 0.1262(4) 0.0841(16) Uani 1 1 d . . .
H4 H 0.5773 0.8627 0.1234 0.101 Uiso 1 1 calc R . .
C23 C 0.8558(11) 0.9649(7) 0.3710(7) 0.147(5) Uani 1 1 d . . .
H23 H 0.8521 1.0366 0.3580 0.176 Uiso 1 1 calc R . .
C22 C 0.9403(10) 0.9268(6) 0.3414(5) 0.129(3) Uani 1 1 d . . .
H22 H 0.9904 0.9700 0.3055 0.155 Uiso 1 1 calc R . .
C24 C 0.7786(7) 0.8976(6) 0.4190(7) 0.130(3) Uani 1 1 d . . .
H24 H 0.7205 0.9228 0.4375 0.156 Uiso 1 1 calc R . .


_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
C32 C33 1.365(5) . ?
C32 C31 1.390(5) . ?
O2 C13 1.378(5) . ?
O2 C17 1.443(6) . ?
C12 C13 1.361(5) . ?
C12 C11 1.391(5) . ?
O3 C14 1.363(5) . ?
O3 C18 1.423(6) . ?
O6 C34 1.362(5) . ?
O6 C38 1.429(6) . ?
O1 C7 1.220(4) . ?
C13 C14 1.387(5) . ?
C10 C11 1.474(5) . ?
C10 C8 1.485(5) . ?
C10 C9 1.539(6) . ?
C31 C36 1.392(5) . ?
C31 C30 1.471(5) . ?
C11 C16 1.383(5) . ?
O5 C33 1.361(5) . ?
O5 C37 1.410(6) . ?
C34 C35 1.371(5) . ?
C34 C33 1.395(5) . ?
C30 C28 1.480(5) . ?
C30 C29 1.543(5) . ?
O4 C27 1.221(5) . ?
C14 C15 1.381(6) . ?
C29 C39 1.441(6) . ?
C29 C40 1.452(6) . ?
C29 C28 1.543(6) . ?
C9 C20 1.438(6) . ?
C9 C19 1.447(6) . ?
C9 C8 1.533(5) . ?
C40 N4 1.127(5) . ?
C27 C26 1.467(5) . ?
C27 C28 1.494(5) . ?
C6 C1 1.373(6) . ?
C6 C5 1.374(6) . ?
C6 C7 1.475(5) . ?
C35 C36 1.368(6) . ?
C26 C21 1.380(6) . ?
C26 C25 1.381(7) . ?
C19 N1 1.137(6) . ?
C7 C8 1.486(5) . ?
C15 C16 1.371(6) . ?
C20 N2 1.132(6) . ?
C1 C2 1.382(7) . ?
C39 N3 1.120(6) . ?
C5 C4 1.412(7) . ?
C17 C18 1.464(7) . ?
C2 C3 1.351(8) . ?
C3 C4 1.359(8) . ?
C21 C22 1.364(9) . ?
C25 C24 1.363(8) . ?
C38 C37 1.462(7) . ?
C23 C24 1.348(13) . ?
C23 C22 1.382(13) . ?

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
C33 C32 C31 121.3(3) . . ?
C13 O2 C17 113.9(3) . . ?
C13 C12 C11 121.0(3) . . ?
C14 O3 C18 112.8(3) . . ?
C34 O6 C38 111.8(3) . . ?
C12 C13 O2 117.5(3) . . ?
C12 C13 C14 120.9(4) . . ?
O2 C13 C14 121.5(4) . . ?
C11 C10 C8 125.1(3) . . ?
C11 C10 C9 120.9(3) . . ?
C8 C10 C9 60.9(2) . . ?
C32 C31 C36 117.8(3) . . ?
C32 C31 C30 117.8(3) . . ?
C36 C31 C30 124.4(3) . . ?
C16 C11 C12 118.0(4) . . ?
C16 C11 C10 123.8(4) . . ?
C12 C11 C10 118.2(3) . . ?
C33 O5 C37 114.3(3) . . ?
O6 C34 C35 119.3(3) . . ?
O6 C34 C33 122.2(4) . . ?
C35 C34 C33 118.6(4) . . ?
C31 C30 C28 124.1(3) . . ?
C31 C30 C29 119.7(3) . . ?
C28 C30 C29 61.3(3) . . ?
O5 C33 C32 117.9(3) . . ?
O5 C33 C34 121.8(4) . . ?
C32 C33 C34 120.3(3) . . ?
O3 C14 C15 119.4(4) . . ?
O3 C14 C13 122.4(4) . . ?
C15 C14 C13 118.2(4) . . ?
C39 C29 C40 114.1(4) . . ?
C39 C29 C28 120.6(3) . . ?
C40 C29 C28 116.0(3) . . ?
C39 C29 C30 118.8(3) . . ?
C40 C29 C30 118.8(3) . . ?
C28 C29 C30 57.3(2) . . ?
C20 C9 C19 113.6(4) . . ?
C20 C9 C8 116.8(3) . . ?
C19 C9 C8 121.0(3) . . ?
C20 C9 C10 117.9(3) . . ?
C19 C9 C10 118.9(3) . . ?
C8 C9 C10 57.8(2) . . ?
N4 C40 C29 177.8(5) . . ?
O4 C27 C26 122.2(4) . . ?
O4 C27 C28 120.3(4) . . ?
C26 C27 C28 117.5(3) . . ?
C1 C6 C5 119.6(4) . . ?
C1 C6 C7 118.1(4) . . ?
C5 C6 C7 122.3(4) . . ?
C36 C35 C34 121.3(3) . . ?
C35 C36 C31 120.7(4) . . ?
C21 C26 C25 119.7(4) . . ?
C21 C26 C27 119.8(4) . . ?
C25 C26 C27 120.4(4) . . ?
C30 C28 C27 119.6(3) . . ?
C30 C28 C29 61.4(2) . . ?
C27 C28 C29 117.2(3) . . ?
N1 C19 C9 177.5(5) . . ?
O1 C7 C6 121.5(4) . . ?
O1 C7 C8 118.7(3) . . ?
C6 C7 C8 119.7(3) . . ?
C16 C15 C14 121.0(4) . . ?
N2 C20 C9 177.8(5) . . ?
C10 C8 C7 118.9(3) . . ?
C10 C8 C9 61.3(2) . . ?
C7 C8 C9 118.2(3) . . ?
C6 C1 C2 121.3(5) . . ?
C15 C16 C11 120.8(4) . . ?
N3 C39 C29 178.7(6) . . ?
C6 C5 C4 118.8(5) . . ?
O2 C17 C18 110.8(4) . . ?
C3 C2 C1 119.0(5) . . ?
C2 C3 C4 121.5(5) . . ?
C22 C21 C26 120.1(7) . . ?
C24 C25 C26 118.9(6) . . ?
O6 C38 C37 110.9(4) . . ?
O3 C18 C17 111.6(4) . . ?
O5 C37 C38 112.7(4) . . ?
C3 C4 C5 119.8(5) . . ?
C24 C23 C22 119.6(7) . . ?
C21 C22 C23 119.8(7) . . ?
C23 C24 C25 121.8(8) . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        27.66
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.070
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_001
_database_code_depnum_ccdc_archive 'CCDC 1891524'
loop_
_audit_author_name
_audit_author_address
'Zhenjie Su' 'Yangzhou University'
_audit_update_record             
;
2019-01-17 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H15 Br N2 O'
_chemical_formula_sum            'C19 H15 Br N2 O'
_chemical_formula_weight         367.23

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5956(17)
_cell_length_b                   5.0269(7)
_cell_length_c                   33.000(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.159(4)
_cell_angle_gamma                90.00
_cell_volume                     1922.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1667
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      21.18

_exptl_crystal_description       blocker
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.143
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7664
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_sigmaI/netI    0.1299
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3352
_reflns_number_gt                1698
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0736P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3256
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_restrained_S_all      0.891
_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
Br1 Br 0.91756(5) -0.42933(12) 0.222912(19) 0.0570(3) Uani 1 1 d . . .
O1 O 0.7499(3) 0.5305(7) 0.08537(11) 0.0533(10) Uani 1 1 d . . .
C8 C 0.4238(4) 0.5567(10) 0.16346(16) 0.0419(14) Uani 1 1 d . . .
H8 H 0.4996 0.6160 0.1626 0.050 Uiso 1 1 calc R . .
C6 C 0.4611(4) 0.2472(10) 0.10445(17) 0.0461(15) Uani 1 1 d . . .
H6A H 0.4849 0.0725 0.1141 0.055 Uiso 1 1 calc R . .
H6B H 0.4144 0.2214 0.0798 0.055 Uiso 1 1 calc R . .
C3 C 0.5663(5) 0.3970(10) 0.09393(16) 0.0431(14) Uani 1 1 d . . .
C4 C 0.6772(5) 0.3607(10) 0.10656(17) 0.0457(15) Uani 1 1 d . . .
C10 C 0.2432(5) 0.5677(14) 0.1940(2) 0.0717(19) Uani 1 1 d . . .
H10 H 0.1951 0.6352 0.2135 0.086 Uiso 1 1 calc R . .
C15 C 0.6787(4) 0.0698(11) 0.16743(17) 0.0480(15) Uani 1 1 d . . .
H15 H 0.6028 0.1187 0.1718 0.058 Uiso 1 1 calc R . .
C18 C 0.9071(5) -0.0650(12) 0.15664(18) 0.0534(15) Uani 1 1 d . . .
H18 H 0.9843 -0.1078 0.1535 0.064 Uiso 1 1 calc R . .
C16 C 0.7314(5) -0.1079(10) 0.19259(17) 0.0473(15) Uani 1 1 d . . .
H16 H 0.6914 -0.1836 0.2136 0.057 Uiso 1 1 calc R . .
C14 C 0.7352(5) 0.1817(11) 0.13514(17) 0.0424(14) Uani 1 1 d . . .
C2 C 0.5681(5) 0.6027(11) 0.06379(17) 0.0468(15) Uani 1 1 d . . .
C13 C 0.3993(5) 0.8676(11) 0.22291(18) 0.0606(17) Uani 1 1 d . . .
H13A H 0.3583 0.8522 0.2475 0.091 Uiso 1 1 calc R . .
H13B H 0.3879 1.0424 0.2117 0.091 Uiso 1 1 calc R . .
H13C H 0.4801 0.8385 0.2286 0.091 Uiso 1 1 calc R . .
C7 C 0.3861(5) 0.3688(10) 0.13563(18) 0.0467(15) Uani 1 1 d . . .
N2 N 0.3963(5) 0.7862(12) 0.02192(17) 0.0801(17) Uani 1 1 d . . .
C1 C 0.6799(6) 0.6746(12) 0.05963(18) 0.0559(16) Uani 1 1 d . . .
C11 C 0.2011(6) 0.3781(14) 0.1676(2) 0.085(2) Uani 1 1 d . . .
H11 H 0.1262 0.3144 0.1695 0.102 Uiso 1 1 calc R . .
C19 C 0.8518(5) 0.1118(11) 0.13116(18) 0.0542(16) Uani 1 1 d . . .
H19 H 0.8927 0.1888 0.1105 0.065 Uiso 1 1 calc R . .
C5 C 0.4742(6) 0.7076(13) 0.04048(18) 0.0572(17) Uani 1 1 d . . .
C9 C 0.3543(5) 0.6612(10) 0.19259(17) 0.0460(15) Uani 1 1 d . . .
C17 C 0.8461(5) -0.1775(10) 0.18684(18) 0.0466(15) Uani 1 1 d . . .
C12 C 0.2721(5) 0.2824(14) 0.1379(2) 0.076(2) Uani 1 1 d . . .
H12 H 0.2431 0.1585 0.1193 0.091 Uiso 1 1 calc R . .
N1 N 0.7351(4) 0.8494(10) 0.03634(15) 0.0708(16) Uani 1 1 d . . .
H1A H 0.6966 0.9466 0.0192 0.085 Uiso 1 1 calc R . .
H1B H 0.8090 0.8640 0.0386 0.085 Uiso 1 1 calc R . .


_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
Br1 C17 1.906(5) . ?
O1 C1 1.361(6) . ?
O1 C4 1.405(6) . ?
C8 C7 1.377(7) . ?
C8 C9 1.382(7) . ?
C6 C3 1.486(7) . ?
C6 C7 1.502(7) . ?
C3 C4 1.349(7) . ?
C3 C2 1.435(7) . ?
C4 C14 1.451(7) . ?
C10 C11 1.369(8) . ?
C10 C9 1.374(8) . ?
C15 C16 1.350(7) . ?
C15 C14 1.391(7) . ?
C18 C19 1.366(7) . ?
C18 C17 1.366(7) . ?
C16 C17 1.395(7) . ?
C14 C19 1.408(7) . ?
C2 C1 1.357(8) . ?
C2 C5 1.412(8) . ?
C13 C9 1.520(7) . ?
C7 C12 1.396(8) . ?
N2 C5 1.142(7) . ?
C1 N1 1.346(7) . ?
C11 C12 1.388(9) . ?

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
C1 O1 C4 106.2(5) . . ?
C7 C8 C9 123.1(5) . . ?
C3 C6 C7 117.1(4) . . ?
C4 C3 C2 105.8(5) . . ?
C4 C3 C6 129.8(5) . . ?
C2 C3 C6 124.1(5) . . ?
C3 C4 O1 110.3(5) . . ?
C3 C4 C14 134.3(5) . . ?
O1 C4 C14 115.3(5) . . ?
C11 C10 C9 121.9(6) . . ?
C16 C15 C14 121.5(5) . . ?
C19 C18 C17 118.3(5) . . ?
C15 C16 C17 119.6(5) . . ?
C15 C14 C19 116.9(5) . . ?
C15 C14 C4 121.9(5) . . ?
C19 C14 C4 121.2(6) . . ?
C1 C2 C5 124.4(6) . . ?
C1 C2 C3 107.5(5) . . ?
C5 C2 C3 128.0(6) . . ?
C8 C7 C12 117.0(6) . . ?
C8 C7 C6 123.9(5) . . ?
C12 C7 C6 119.0(5) . . ?
N1 C1 C2 135.1(6) . . ?
N1 C1 O1 114.7(6) . . ?
C2 C1 O1 110.2(6) . . ?
C10 C11 C12 119.0(6) . . ?
C18 C19 C14 122.3(6) . . ?
N2 C5 C2 178.0(7) . . ?
C10 C9 C8 117.8(6) . . ?
C10 C9 C13 120.7(6) . . ?
C8 C9 C13 121.5(5) . . ?
C18 C17 C16 121.2(5) . . ?
C18 C17 Br1 120.4(4) . . ?
C16 C17 Br1 118.4(5) . . ?
C11 C12 C7 121.2(6) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.095
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_002_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1875320'
loop_
_audit_author_name
_audit_author_address
'Zhenjie Su'
;Yangzhou University
China
;
_audit_update_record             
;
2018-10-25 deposited with the CCDC.	2019-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2 O3'
_chemical_formula_sum            'C20 H16 N2 O3'
_chemical_formula_weight         332.35

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8735(10)
_cell_length_b                   11.1925(13)
_cell_length_c                   16.3751(18)
_cell_angle_alpha                104.559(3)
_cell_angle_beta                 102.943(3)
_cell_angle_gamma                102.875(3)
_cell_volume                     1630.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    9234
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      27.44

_exptl_crystal_description       blocker
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25810
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0427
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         27.55
_reflns_number_total             7544
_reflns_number_gt                4850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0870P)²+0.6021P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7477
_refine_ls_number_parameters     451
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1904
_refine_ls_wR_factor_gt          0.1675
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_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
O3 O 1.11775(15) 0.33816(14) 0.37990(9) 0.0452(4) Uani 1 1 d . . .
C2 C 1.0954(2) 0.4210(2) 0.33011(13) 0.0424(5) Uani 1 1 d . . .
C3 C 1.2048(2) 0.4487(2) 0.28495(13) 0.0425(5) Uani 1 1 d . . .
C4 C 0.7274(2) 0.3602(2) 0.17290(14) 0.0468(5) Uani 1 1 d . . .
H4 H 0.7316 0.3085 0.2093 0.056 Uiso 1 1 calc R . .
C5 C 1.0112(2) 0.3230(2) 0.41851(13) 0.0446(5) Uani 1 1 d . . .
N2 N 1.0189(2) 0.2504(2) 0.47245(13) 0.0578(5) Uani 1 1 d . . .
H2A H 1.0891 0.2169 0.4805 0.069 Uiso 1 1 calc R . .
H2B H 0.9536 0.2375 0.4989 0.069 Uiso 1 1 calc R . .
C7 C 0.8134(2) 0.4870(2) 0.20534(14) 0.0445(5) Uani 1 1 d . . .
C8 C 0.7949(2) 0.4004(2) 0.42267(14) 0.0492(5) Uani 1 1 d . . .
O1 O 0.55306(19) 0.18158(17) 0.05924(11) 0.0676(5) Uani 1 1 d . . .
O2 O 0.53430(19) 0.33981(19) -0.05104(11) 0.0695(5) Uani 1 1 d . . .
N1 N 0.6936(2) 0.4082(2) 0.44363(15) 0.0693(6) Uani 1 1 d . . .
C12 C 0.9761(2) 0.4569(2) 0.33849(13) 0.0427(5) Uani 1 1 d . . .
C13 C 1.1896(2) 0.5150(2) 0.22394(15) 0.0524(6) Uani 1 1 d . . .
H13 H 1.1066 0.5412 0.2102 0.063 Uiso 1 1 calc R . .
C14 C 0.6270(2) 0.3854(2) 0.03344(14) 0.0505(5) Uani 1 1 d . . .
C15 C 0.9101(2) 0.5466(2) 0.30012(14) 0.0497(5) Uani 1 1 d . . .
H15A H 0.9880 0.6194 0.3033 0.060 Uiso 1 1 calc R . .
H15B H 0.8533 0.5799 0.3366 0.060 Uiso 1 1 calc R . .
C16 C 0.6349(2) 0.3081(2) 0.08746(14) 0.0468(5) Uani 1 1 d . . .
C17 C 1.2956(3) 0.5427(2) 0.18326(16) 0.0557(6) Uani 1 1 d . . .
H17 H 1.2836 0.5878 0.1429 0.067 Uiso 1 1 calc R . .
C18 C 0.9199(2) 0.3924(2) 0.39515(13) 0.0439(5) Uani 1 1 d . . .
C19 C 1.3294(3) 0.4097(3) 0.30272(17) 0.0597(6) Uani 1 1 d . . .
H19 H 1.3419 0.3639 0.3426 0.072 Uiso 1 1 calc R . .
C20 C 0.7143(3) 0.5108(3) 0.06467(17) 0.0599(6) Uani 1 1 d . . .
H20 H 0.7112 0.5620 0.0279 0.072 Uiso 1 1 calc R . .
C21 C 0.8062(3) 0.5618(2) 0.14955(16) 0.0543(6) Uani 1 1 d . . .
H21 H 0.8642 0.6473 0.1698 0.065 Uiso 1 1 calc R . .
C22 C 1.4188(3) 0.5041(2) 0.20200(16) 0.0583(6) Uani 1 1 d . . .
H22 H 1.4901 0.5224 0.1745 0.070 Uiso 1 1 calc R . .
C23 C 1.4346(3) 0.4382(3) 0.26189(19) 0.0689(7) Uani 1 1 d . . .
H23 H 1.5178 0.4122 0.2752 0.083 Uiso 1 1 calc R . .
C24 C 0.4328(5) 0.2208(3) -0.0688(3) 0.1295(17) Uani 1 1 d D . .
H24A H 0.3477 0.2383 -0.0542 0.155 Uiso 1 1 calc R . .
H24B H 0.4034 0.1785 -0.1321 0.155 Uiso 1 1 calc R . .
C25 C 0.4665(5) 0.1350(4) -0.0301(2) 0.1239(16) Uani 1 1 d D . .
H25A H 0.5164 0.0866 -0.0644 0.149 Uiso 1 1 calc R . .
H25B H 0.3762 0.0744 -0.0342 0.149 Uiso 1 1 calc R . .
O6 O 0.66997(16) 0.79447(15) 0.40036(11) 0.0554(4) Uani 1 1 d . . .
C27 C 0.3718(2) 0.9884(2) 0.25512(16) 0.0524(6) Uani 1 1 d . . .
O4 O 0.0941(2) 0.7159(2) 0.08434(12) 0.0786(6) Uani 1 1 d . . .
C29 C 0.3302(3) 0.8214(2) 0.43335(15) 0.0538(6) Uani 1 1 d . . .
C30 C 0.5274(2) 0.9190(2) 0.37117(14) 0.0477(5) Uani 1 1 d . . .
N3 N 0.5580(2) 0.6744(2) 0.47418(15) 0.0690(6) Uani 1 1 d . . .
H3A H 0.6299 0.6426 0.4813 0.083 Uiso 1 1 calc R . .
H3B H 0.4874 0.6503 0.4948 0.083 Uiso 1 1 calc R . .
C32 C 0.2763(2) 0.8677(2) 0.20971(15) 0.0520(5) Uani 1 1 d . . .
H32 H 0.2718 0.8036 0.2366 0.062 Uiso 1 1 calc R . .
C33 C 0.6509(2) 0.8917(2) 0.36256(15) 0.0500(5) Uani 1 1 d . . .
C34 C 0.1865(3) 0.8390(3) 0.12488(16) 0.0575(6) Uani 1 1 d . . .
C35 C 0.5559(2) 0.7608(2) 0.43110(15) 0.0517(5) Uani 1 1 d . . .
C36 C 0.7660(2) 0.9394(2) 0.32634(15) 0.0511(5) Uani 1 1 d . . .
N4 N 0.2213(2) 0.8135(2) 0.44773(16) 0.0728(6) Uani 1 1 d . . .
C38 C 0.4639(2) 0.8326(2) 0.41395(14) 0.0493(5) Uani 1 1 d . . .
C39 C 0.4665(3) 1.0216(2) 0.34880(16) 0.0572(6) Uani 1 1 d . . .
H39A H 0.5471 1.0976 0.3607 0.069 Uiso 1 1 calc R . .
H39B H 0.4099 1.0446 0.3884 0.069 Uiso 1 1 calc R . .
C40 C 0.7509(3) 1.0178(2) 0.27330(17) 0.0600(6) Uani 1 1 d . . .
H40 H 0.6659 1.0415 0.2612 0.072 Uiso 1 1 calc R . .
C41 C 0.8949(3) 0.9068(3) 0.34330(19) 0.0690(7) Uani 1 1 d . . .
H41 H 0.9083 0.8551 0.3790 0.083 Uiso 1 1 calc R . .
O5 O 0.1083(3) 0.9097(3) -0.00064(16) 0.1035(8) Uani 1 1 d . . .
C43 C 0.8597(3) 1.0610(3) 0.23832(19) 0.0675(7) Uani 1 1 d . . .
H43 H 0.8479 1.1137 0.2031 0.081 Uiso 1 1 calc R . .
C44 C 0.1922(3) 0.9338(3) 0.08434(19) 0.0703(8) Uani 1 1 d . . .
C45 C 0.3769(3) 1.0829(3) 0.2142(2) 0.0726(8) Uani 1 1 d . . .
H45 H 0.4410 1.1654 0.2436 0.087 Uiso 1 1 calc R . .
C46 C 0.2874(4) 1.0549(4) 0.1301(2) 0.0859(10) Uani 1 1 d . . .
H46 H 0.2912 1.1195 0.1036 0.103 Uiso 1 1 calc R . .
C47 C 1.0029(3) 0.9501(3) 0.3080(2) 0.0829(9) Uani 1 1 d . . .
H47 H 1.0885 0.9272 0.3201 0.100 Uiso 1 1 calc R . .
C48 C 0.9859(3) 1.0263(3) 0.2553(2) 0.0776(8) Uani 1 1 d . . .
H48 H 1.0589 1.0546 0.2312 0.093 Uiso 1 1 calc R . .
C49 C -0.0075(6) 0.7927(5) -0.0293(3) 0.1420(19) Uani 1 1 d . . .
H49A H -0.0855 0.8116 -0.0064 0.170 Uiso 1 1 calc R . .
H49B H -0.0440 0.7667 -0.0932 0.170 Uiso 1 1 calc R . .
C50 C 0.0217(4) 0.6860(5) -0.0062(2) 0.1202(15) Uani 1 1 d . . .
H50A H 0.0809 0.6522 -0.0406 0.144 Uiso 1 1 calc R . .
H50B H -0.0694 0.6187 -0.0217 0.144 Uiso 1 1 calc R . .


_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
O3 C5 1.345(2) . ?
O3 C2 1.402(2) . ?
C2 C12 1.350(3) . ?
C2 C3 1.461(3) . ?
C3 C13 1.388(3) . ?
C3 C19 1.390(3) . ?
C4 C7 1.378(3) . ?
C4 C16 1.383(3) . ?
C5 N2 1.343(3) . ?
C5 C18 1.367(3) . ?
C7 C21 1.387(3) . ?
C7 C15 1.516(3) . ?
C8 N1 1.142(3) . ?
C8 C18 1.418(3) . ?
O1 C16 1.366(3) . ?
O1 C25 1.414(4) . ?
O2 C14 1.372(3) . ?
O2 C24 1.394(4) . ?
C12 C18 1.442(3) . ?
C12 C15 1.500(3) . ?
C13 C17 1.381(3) . ?
C14 C20 1.370(3) . ?
C14 C16 1.386(3) . ?
C17 C22 1.377(3) . ?
C19 C23 1.378(3) . ?
C20 C21 1.374(3) . ?
C22 C23 1.370(3) . ?
C24 C25 1.338(5) . ?
O6 C35 1.350(3) . ?
O6 C33 1.407(3) . ?
C27 C32 1.371(3) . ?
C27 C45 1.385(3) . ?
C27 C39 1.511(3) . ?
O4 C34 1.371(3) . ?
O4 C50 1.411(4) . ?
C29 N4 1.141(3) . ?
C29 C38 1.412(3) . ?
C30 C33 1.349(3) . ?
C30 C38 1.444(3) . ?
C30 C39 1.495(3) . ?
N3 C35 1.334(3) . ?
C32 C34 1.384(3) . ?
C33 C36 1.456(3) . ?
C34 C44 1.384(4) . ?
C35 C38 1.369(3) . ?
C36 C41 1.389(3) . ?
C36 C40 1.389(3) . ?
C40 C43 1.379(3) . ?
C41 C47 1.376(4) . ?
O5 C44 1.375(3) . ?
O5 C49 1.423(6) . ?
C43 C48 1.376(4) . ?
C44 C46 1.374(5) . ?
C45 C46 1.374(4) . ?
C47 C48 1.367(4) . ?
C49 C50 1.409(6) . ?

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
C5 O3 C2 107.76(15) . . ?
C12 C2 O3 109.30(16) . . ?
C12 C2 C3 136.43(19) . . ?
O3 C2 C3 114.25(17) . . ?
C13 C3 C19 117.70(19) . . ?
C13 C3 C2 121.90(19) . . ?
C19 C3 C2 120.41(19) . . ?
C7 C4 C16 121.48(19) . . ?
N2 C5 O3 116.04(19) . . ?
N2 C5 C18 134.18(19) . . ?
O3 C5 C18 109.71(17) . . ?
C4 C7 C21 118.2(2) . . ?
C4 C7 C15 121.84(19) . . ?
C21 C7 C15 119.9(2) . . ?
N1 C8 C18 178.6(2) . . ?
C16 O1 C25 114.7(2) . . ?
C14 O2 C24 112.9(2) . . ?
C2 C12 C18 106.23(18) . . ?
C2 C12 C15 129.52(19) . . ?
C18 C12 C15 124.24(18) . . ?
C17 C13 C3 121.1(2) . . ?
C20 C14 O2 118.7(2) . . ?
C20 C14 C16 119.4(2) . . ?
O2 C14 C16 121.8(2) . . ?
C12 C15 C7 115.25(18) . . ?
O1 C16 C4 118.55(19) . . ?
O1 C16 C14 122.1(2) . . ?
C4 C16 C14 119.4(2) . . ?
C22 C17 C13 120.5(2) . . ?
C5 C18 C8 126.25(19) . . ?
C5 C18 C12 106.99(18) . . ?
C8 C18 C12 126.8(2) . . ?
C23 C19 C3 120.7(2) . . ?
C14 C20 C21 120.9(2) . . ?
C20 C21 C7 120.6(2) . . ?
C23 C22 C17 118.9(2) . . ?
C22 C23 C19 121.1(2) . . ?
C25 C24 O2 120.7(3) . . ?
C24 C25 O1 118.2(3) . . ?
C35 O6 C33 107.85(17) . . ?
C32 C27 C45 118.4(2) . . ?
C32 C27 C39 121.9(2) . . ?
C45 C27 C39 119.7(2) . . ?
C34 O4 C50 115.4(3) . . ?
N4 C29 C38 178.6(3) . . ?
C33 C30 C38 106.1(2) . . ?
C33 C30 C39 129.8(2) . . ?
C38 C30 C39 123.96(19) . . ?
C27 C32 C34 121.7(2) . . ?
C30 C33 O6 109.37(19) . . ?
C30 C33 C36 135.8(2) . . ?
O6 C33 C36 114.78(19) . . ?
O4 C34 C44 122.5(2) . . ?
O4 C34 C32 117.9(2) . . ?
C44 C34 C32 119.6(3) . . ?
N3 C35 O6 117.1(2) . . ?
N3 C35 C38 133.6(2) . . ?
O6 C35 C38 109.2(2) . . ?
C41 C36 C40 117.7(2) . . ?
C41 C36 C33 120.8(2) . . ?
C40 C36 C33 121.5(2) . . ?
C35 C38 C29 125.7(2) . . ?
C35 C38 C30 107.46(19) . . ?
C29 C38 C30 126.8(2) . . ?
C30 C39 C27 116.66(19) . . ?
C43 C40 C36 121.1(2) . . ?
C47 C41 C36 120.9(3) . . ?
C44 O5 C49 111.3(3) . . ?
C48 C43 C40 120.1(3) . . ?
C46 C44 O5 119.3(3) . . ?
C46 C44 C34 118.7(3) . . ?
O5 C44 C34 122.1(3) . . ?
C46 C45 C27 120.1(3) . . ?
C44 C46 C45 121.5(3) . . ?
C48 C47 C41 120.7(3) . . ?
C47 C48 C43 119.5(2) . . ?
C50 C49 O5 118.2(3) . . ?
C49 C50 O4 113.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.043
