# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 2523773'
loop_
_audit_author_name
_audit_author_address
'Guangxin Yang'
;Shanghai JiaoTong University
China
;
_audit_update_record             
;
2026-01-18 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 N O2'
_chemical_formula_sum            'C18 H13 N O2'
_chemical_formula_weight         275.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.8308(5)
_cell_length_b                   12.1154(10)
_cell_length_c                   8.1913(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.093(4)
_cell_angle_gamma                90
_cell_volume                     654.51(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2679
_cell_measurement_theta_min      5.59
_cell_measurement_theta_max      68.07

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.736
_shelx_estimated_absorpt_T_min   0.891
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6071
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.594
_diffrn_reflns_theta_max         68.348
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1260
_reflns_number_gt                1025
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.1515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0092(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1260
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7770(3) 0.750000 0.7546(3) 0.0484(5) Uani 1 2 d S T P . .
H1 H 0.888(5) 0.750000 0.837(4) 0.073 Uiso 1 2 d S U P . .
C1 C 0.6805(2) 0.65431(14) 0.6870(2) 0.0454(4) Uani 1 1 d . . . . .
C2 C 0.4928(2) 0.68643(12) 0.54996(18) 0.0378(4) Uani 1 1 d . . . . .
H2 H 0.502360 0.658482 0.440023 0.045 Uiso 1 1 calc R U . . .
C3 C 0.29576(19) 0.64288(11) 0.59037(17) 0.0345(3) Uani 1 1 d . . . . .
H3 H 0.290238 0.562059 0.591392 0.041 Uiso 1 1 calc R U . . .
C4 C 0.12041(19) 0.69249(11) 0.45756(16) 0.0337(3) Uani 1 1 d . . . . .
C5 C -0.0301(2) 0.63484(13) 0.34371(19) 0.0417(4) Uani 1 1 d . . . . .
H5 H -0.029264 0.558084 0.342433 0.050 Uiso 1 1 calc R U . . .
C6 C -0.1823(2) 0.69308(14) 0.2315(2) 0.0492(4) Uani 1 1 d . . . . .
H6 H -0.285116 0.655023 0.155614 0.059 Uiso 1 1 calc R U . . .
C7 C 0.28921(18) 0.69229(12) 0.75860(17) 0.0341(3) Uani 1 1 d . . . . .
C8 C 0.2795(2) 0.63484(15) 0.90261(19) 0.0460(4) Uani 1 1 d . . . . .
H8 H 0.281448 0.558089 0.903469 0.055 Uiso 1 1 calc R U . . .
C9 C 0.2667(2) 0.69306(17) 1.0458(2) 0.0577(5) Uani 1 1 d . . . . .
H9 H 0.258121 0.654950 1.142276 0.069 Uiso 1 1 calc R U . . .
O1 O 0.73560(18) 0.56202(11) 0.73140(19) 0.0707(4) 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
N1 C1 1.3767(19) 4_575 ?
N1 C1 1.3767(19) . ?
C1 O1 1.205(2) . ?
C1 C2 1.518(2) . ?
C2 C2 1.540(3) 4_575 ?
C2 C3 1.5597(19) . ?
C3 C7 1.5137(19) . ?
C3 C4 1.5169(18) . ?
C4 C5 1.3839(19) . ?
C4 C4 1.394(3) 4_575 ?
C5 C6 1.388(2) . ?
C6 C6 1.379(3) 4_575 ?
C7 C8 1.386(2) . ?
C7 C7 1.398(3) 4_575 ?
C8 C9 1.391(3) . ?
C9 C9 1.380(4) 4_575 ?

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 N1 C1 114.73(18) 4_575 . ?
O1 C1 N1 125.48(15) . . ?
O1 C1 C2 126.75(15) . . ?
N1 C1 C2 107.77(14) . . ?
C1 C2 C2 104.86(8) . 4_575 ?
C1 C2 C3 111.44(12) . . ?
C2 C2 C3 109.78(7) 4_575 . ?
C7 C3 C4 106.93(11) . . ?
C7 C3 C2 106.92(11) . . ?
C4 C3 C2 106.12(11) . . ?
C5 C4 C4 120.31(9) . 4_575 ?
C5 C4 C3 126.34(13) . . ?
C4 C4 C3 113.34(7) 4_575 . ?
C4 C5 C6 119.12(15) . . ?
C6 C6 C5 120.56(9) 4_575 . ?
C8 C7 C7 120.14(10) . 4_575 ?
C8 C7 C3 126.55(14) . . ?
C7 C7 C3 113.30(8) 4_575 . ?
C7 C8 C9 119.38(17) . . ?
C9 C9 C8 120.47(10) 4_575 . ?

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
C1 N1 C1 O1 -177.62(12) 4_575 . . . ?
C1 N1 C1 C2 1.6(2) 4_575 . . . ?
O1 C1 C2 C2 178.30(15) . . . 4_575 ?
N1 C1 C2 C2 -0.88(14) . . . 4_575 ?
O1 C1 C2 C3 59.6(2) . . . . ?
N1 C1 C2 C3 -119.58(15) . . . . ?
C1 C2 C3 C7 59.00(15) . . . . ?
C2 C2 C3 C7 -56.72(10) 4_575 . . . ?
C1 C2 C3 C4 172.88(11) . . . . ?
C2 C2 C3 C4 57.16(10) 4_575 . . . ?
C7 C3 C4 C5 -125.52(14) . . . . ?
C2 C3 C4 C5 120.61(14) . . . . ?
C7 C3 C4 C4 54.43(10) . . . 4_575 ?
C2 C3 C4 C4 -59.44(10) . . . 4_575 ?
C4 C4 C5 C6 -0.93(16) 4_575 . . . ?
C3 C4 C5 C6 179.02(13) . . . . ?
C4 C5 C6 C6 0.93(16) . . . 4_575 ?
C4 C3 C7 C8 124.20(14) . . . . ?
C2 C3 C7 C8 -122.46(14) . . . . ?
C4 C3 C7 C7 -54.40(10) . . . 4_575 ?
C2 C3 C7 C7 58.93(10) . . . 4_575 ?
C7 C7 C8 C9 0.94(16) 4_575 . . . ?
C3 C7 C8 C9 -177.58(12) . . . . ?
C7 C8 C9 C9 -0.95(16) . . . 4_575 ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_t_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2523775'
loop_
_audit_author_name
_audit_author_address
'Guangxin Yang'
;Shanghai JiaoTong University
China
;
_audit_update_record             
;
2026-01-18 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 Br2 N O2'
_chemical_formula_sum            'C18 H11 Br2 N O2'
_chemical_formula_weight         433.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.5007(14)
_cell_length_b                   9.0346(13)
_cell_length_c                   15.407(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.696(11)
_cell_angle_gamma                90
_cell_volume                     1507.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9287
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      68.35

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.909
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   0.5269
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    6.902
_shelx_estimated_absorpt_T_min   0.339
_shelx_estimated_absorpt_T_max   0.405
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9990
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.769
_diffrn_reflns_theta_max         68.264
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2691
_reflns_number_gt                2680
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+2.1787P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2691
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0614
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.69403(3) 0.08100(3) 0.34813(2) 0.03256(10) Uani 1 1 d . . . . .
H1 H 0.959(3) 0.092(4) 0.696(2) 0.037(9) Uiso 1 1 d . . . . .
C1 C 0.74241(19) 0.3947(2) 0.37777(15) 0.0187(4) Uani 1 1 d . . . . .
N1 N 0.93664(19) 0.1490(2) 0.65163(15) 0.0236(4) Uani 1 1 d . . . . .
O1 O 0.8873(2) -0.0306(2) 0.53990(14) 0.0448(5) Uani 1 1 d . . . . .
Br2 Br 0.85261(2) 0.65273(2) 0.61646(2) 0.02151(9) Uani 1 1 d . . . . .
C2 C 0.7136(2) 0.4109(3) 0.28300(16) 0.0260(5) Uani 1 1 d . . . . .
H2 H 0.692148 0.327060 0.243550 0.031 Uiso 1 1 calc R U . . .
O2 O 0.97938(17) 0.36693(18) 0.73357(11) 0.0290(4) Uani 1 1 d . . . . .
C5 C 0.77822(19) 0.6585(2) 0.39974(16) 0.0192(4) Uani 1 1 d . . . . .
H5 H 0.800488 0.742386 0.439101 0.023 Uiso 1 1 calc R U . . .
C4 C 0.7479(2) 0.6743(3) 0.30427(17) 0.0240(5) Uani 1 1 d . . . . .
H4 H 0.748756 0.769754 0.278688 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7165(2) 0.5520(3) 0.24659(17) 0.0288(5) Uani 1 1 d . . . . .
H3 H 0.697003 0.564209 0.181989 0.035 Uiso 1 1 calc R U . . .
C7 C 0.80388(18) 0.4787(2) 0.53819(14) 0.0151(4) Uani 1 1 d . . . . .
C6 C 0.77524(18) 0.5179(2) 0.43611(14) 0.0162(4) Uani 1 1 d . . . . .
C8 C 0.91310(19) 0.3669(2) 0.56345(15) 0.0167(4) Uani 1 1 d . . . . .
H8 H 0.987444 0.416734 0.557075 0.020 Uiso 1 1 calc R U . . .
C9 C 0.8787(2) 0.2319(2) 0.49752(15) 0.0188(4) Uani 1 1 d . . . . .
H9 H 0.936078 0.226129 0.461227 0.023 Uiso 1 1 calc R U . . .
C10 C 0.7429(2) 0.2513(2) 0.43039(15) 0.0196(4) Uani 1 1 d . . . . .
C11 C 0.65941(19) 0.2738(2) 0.48784(15) 0.0192(4) Uani 1 1 d . . . . .
C12 C 0.69240(19) 0.3982(2) 0.54603(14) 0.0170(4) Uani 1 1 d . . . . .
C13 C 0.6255(2) 0.4363(3) 0.60251(15) 0.0209(5) Uani 1 1 d . . . . .
H13 H 0.648624 0.519668 0.642187 0.025 Uiso 1 1 calc R U . . .
C14 C 0.5239(2) 0.3506(3) 0.60035(17) 0.0273(5) Uani 1 1 d . . . . .
H14 H 0.477383 0.375706 0.638840 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4902(2) 0.2295(3) 0.54261(18) 0.0296(6) Uani 1 1 d . . . . .
H15 H 0.420277 0.172587 0.541421 0.036 Uiso 1 1 calc R U . . .
C16 C 0.5575(2) 0.1897(3) 0.48603(17) 0.0262(5) Uani 1 1 d . . . . .
H16 H 0.533981 0.105939 0.446685 0.031 Uiso 1 1 calc R U . . .
C17 C 0.94674(19) 0.3010(2) 0.66078(15) 0.0195(4) Uani 1 1 d . . . . .
C18 C 0.8988(2) 0.0982(3) 0.56168(17) 0.0255(5) 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 C10 1.952(2) . ?
C1 C2 1.392(3) . ?
C1 C6 1.400(3) . ?
C1 C10 1.528(3) . ?
N1 C17 1.381(3) . ?
N1 C18 1.383(3) . ?
N1 H1 0.83(3) . ?
O1 C18 1.206(3) . ?
Br2 C7 1.945(2) . ?
C2 C3 1.398(4) . ?
C2 H2 0.9500 . ?
O2 C17 1.212(3) . ?
C5 C6 1.393(3) . ?
C5 C4 1.400(3) . ?
C5 H5 0.9500 . ?
C4 C3 1.387(4) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C7 C12 1.514(3) . ?
C7 C6 1.536(3) . ?
C7 C8 1.556(3) . ?
C8 C17 1.537(3) . ?
C8 C9 1.551(3) . ?
C8 H8 1.0000 . ?
C9 C18 1.528(3) . ?
C9 C10 1.565(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.523(3) . ?
C11 C16 1.389(3) . ?
C11 C12 1.408(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.393(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
C2 C1 C6 120.5(2) . . ?
C2 C1 C10 127.1(2) . . ?
C6 C1 C10 112.44(18) . . ?
C17 N1 C18 114.8(2) . . ?
C17 N1 H1 123(2) . . ?
C18 N1 H1 122(2) . . ?
C1 C2 C3 119.2(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C12 C7 C6 107.30(16) . . ?
C12 C7 C8 107.58(16) . . ?
C6 C7 C8 106.40(16) . . ?
C12 C7 Br2 114.43(15) . . ?
C6 C7 Br2 111.47(14) . . ?
C8 C7 Br2 109.28(13) . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 C7 126.6(2) . . ?
C1 C6 C7 113.10(18) . . ?
C17 C8 C9 105.01(17) . . ?
C17 C8 C7 114.34(17) . . ?
C9 C8 C7 109.91(16) . . ?
C17 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
C18 C9 C8 104.37(18) . . ?
C18 C9 C10 114.59(18) . . ?
C8 C9 C10 108.79(17) . . ?
C18 C9 H9 109.6 . . ?
C8 C9 H9 109.6 . . ?
C10 C9 H9 109.6 . . ?
C11 C10 C1 107.76(18) . . ?
C11 C10 C9 108.36(17) . . ?
C1 C10 C9 105.67(17) . . ?
C11 C10 Br1 112.50(15) . . ?
C1 C10 Br1 112.04(15) . . ?
C9 C10 Br1 110.21(14) . . ?
C16 C11 C12 119.6(2) . . ?
C16 C11 C10 127.4(2) . . ?
C12 C11 C10 112.92(18) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 C7 126.5(2) . . ?
C11 C12 C7 112.74(19) . . ?
C12 C13 C14 119.1(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 119.2(2) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
O2 C17 N1 124.9(2) . . ?
O2 C17 C8 127.6(2) . . ?
N1 C17 C8 107.50(19) . . ?
O1 C18 N1 124.5(2) . . ?
O1 C18 C9 127.2(2) . . ?
N1 C18 C9 108.30(19) . . ?

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
C6 C1 C2 C3 -0.6(3) . . . . ?
C10 C1 C2 C3 179.2(2) . . . . ?
C6 C5 C4 C3 -0.7(3) . . . . ?
C5 C4 C3 C2 0.7(4) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C5 C6 C7 -179.27(19) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C10 C1 C6 C5 -179.23(19) . . . . ?
C2 C1 C6 C7 -180.0(2) . . . . ?
C10 C1 C6 C7 0.2(2) . . . . ?
C12 C7 C6 C5 124.0(2) . . . . ?
C8 C7 C6 C5 -121.0(2) . . . . ?
Br2 C7 C6 C5 -2.0(3) . . . . ?
C12 C7 C6 C1 -55.3(2) . . . . ?
C8 C7 C6 C1 59.6(2) . . . . ?
Br2 C7 C6 C1 178.67(14) . . . . ?
C12 C7 C8 C17 -59.0(2) . . . . ?
C6 C7 C8 C17 -173.76(17) . . . . ?
Br2 C7 C8 C17 65.76(19) . . . . ?
C12 C7 C8 C9 58.8(2) . . . . ?
C6 C7 C8 C9 -56.0(2) . . . . ?
Br2 C7 C8 C9 -176.44(14) . . . . ?
C17 C8 C9 C18 -1.7(2) . . . . ?
C7 C8 C9 C18 -125.14(19) . . . . ?
C17 C8 C9 C10 121.06(18) . . . . ?
C7 C8 C9 C10 -2.4(2) . . . . ?
C2 C1 C10 C11 -125.2(2) . . . . ?
C6 C1 C10 C11 54.7(2) . . . . ?
C2 C1 C10 C9 119.1(2) . . . . ?
C6 C1 C10 C9 -61.0(2) . . . . ?
C2 C1 C10 Br1 -0.9(3) . . . . ?
C6 C1 C10 Br1 178.93(14) . . . . ?
C18 C9 C10 C11 61.4(2) . . . . ?
C8 C9 C10 C11 -55.0(2) . . . . ?
C18 C9 C10 C1 176.63(18) . . . . ?
C8 C9 C10 C1 60.3(2) . . . . ?
C18 C9 C10 Br1 -62.1(2) . . . . ?
C8 C9 C10 Br1 -178.50(14) . . . . ?
C1 C10 C11 C16 123.4(2) . . . . ?
C9 C10 C11 C16 -122.7(2) . . . . ?
Br1 C10 C11 C16 -0.6(3) . . . . ?
C1 C10 C11 C12 -54.8(2) . . . . ?
C9 C10 C11 C12 59.1(2) . . . . ?
Br1 C10 C11 C12 -178.77(14) . . . . ?
C16 C11 C12 C13 1.0(3) . . . . ?
C10 C11 C12 C13 179.30(19) . . . . ?
C16 C11 C12 C7 -178.93(19) . . . . ?
C10 C11 C12 C7 -0.6(2) . . . . ?
C6 C7 C12 C13 -124.7(2) . . . . ?
C8 C7 C12 C13 121.2(2) . . . . ?
Br2 C7 C12 C13 -0.4(3) . . . . ?
C6 C7 C12 C11 55.3(2) . . . . ?
C8 C7 C12 C11 -58.9(2) . . . . ?
Br2 C7 C12 C11 179.50(14) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C7 C12 C13 C14 179.2(2) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C12 C11 C16 C15 -0.5(3) . . . . ?
C10 C11 C16 C15 -178.5(2) . . . . ?
C14 C15 C16 C11 -0.3(4) . . . . ?
C18 N1 C17 O2 -179.4(2) . . . . ?
C18 N1 C17 C8 -1.0(3) . . . . ?
C9 C8 C17 O2 180.0(2) . . . . ?
C7 C8 C17 O2 -59.4(3) . . . . ?
C9 C8 C17 N1 1.7(2) . . . . ?
C7 C8 C17 N1 122.2(2) . . . . ?
C17 N1 C18 O1 178.3(3) . . . . ?
C17 N1 C18 C9 -0.2(3) . . . . ?
C8 C9 C18 O1 -177.2(3) . . . . ?
C10 C9 C18 O1 63.9(3) . . . . ?
C8 C9 C18 N1 1.2(2) . . . . ?
C10 C9 C18 N1 -117.7(2) . . . . ?

_refine_diff_density_max         0.661
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_t_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2523774'
loop_
_audit_author_name
_audit_author_address
'Guangxin Yang'
;Shanghai JiaoTong University
China
;
_audit_update_record             
;
2026-01-18 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 Br N O2'
_chemical_formula_sum            'C19 H14 Br N O2'
_chemical_formula_weight         368.22

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'
Br Br -0.6763 1.2805 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.011(3)
_cell_length_b                   17.559(4)
_cell_length_c                   10.817(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.964(14)
_cell_angle_gamma                90
_cell_volume                     1462.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7488
_cell_measurement_theta_min      4.94
_cell_measurement_theta_max      68.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.672
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   0.6007
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    3.910
_shelx_estimated_absorpt_T_min   0.540
_shelx_estimated_absorpt_T_max   0.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14304
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.942
_diffrn_reflns_theta_max         68.532
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2661
_reflns_number_gt                2267
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1381P)²+4.1064P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2661
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0821
_refine_ls_wR_factor_ref         0.2634
_refine_ls_wR_factor_gt          0.2574
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.77727(13) 0.75613(7) 0.64349(11) 0.1075(5) Uani 1 1 d . . . . .
C1 C 0.7043(8) 0.8827(4) 0.8572(6) 0.0625(15) Uani 1 1 d . . . . .
N1 N 0.6013(7) 0.9276(3) 0.9095(4) 0.0551(11) Uani 1 1 d . . . . .
H1 H 0.618252 0.975667 0.922173 0.066 Uiso 1 1 calc R U . . .
O1 O 0.8284(7) 0.9055(4) 0.8254(6) 0.0954(18) Uani 1 1 d . . . . .
O2 O 0.3677(5) 0.9169(2) 0.9924(4) 0.0566(10) Uani 1 1 d . . . . .
C2 C 0.6353(7) 0.8019(3) 0.8469(5) 0.0493(12) Uani 1 1 d . . . . .
H2 H 0.721910 0.767893 0.901249 0.059 Uiso 1 1 calc R U . . .
C4 C 0.4687(7) 0.8892(3) 0.9400(5) 0.0480(12) Uani 1 1 d . . . . .
C3 C 0.4739(7) 0.8069(3) 0.8984(5) 0.0443(11) Uani 1 1 d . . . . .
H3 H 0.488046 0.773068 0.972601 0.053 Uiso 1 1 calc R U . . .
C6 C 0.3386(8) 0.7043(3) 0.7538(5) 0.0539(13) Uani 1 1 d . . . . .
C5 C 0.3049(7) 0.7850(3) 0.7906(5) 0.0484(12) Uani 1 1 d . . . . .
C7 C 0.4813(8) 0.6958(3) 0.7090(5) 0.0524(13) Uani 1 1 d . . . . .
C9 C 0.5240(10) 0.6244(4) 0.6695(6) 0.0731(19) Uani 1 1 d . . . . .
H9 H 0.619464 0.618101 0.637274 0.088 Uiso 1 1 calc R U . . .
C8 C 0.5774(8) 0.7710(3) 0.7071(5) 0.0539(13) Uani 1 1 d . . . . .
C10 C 0.4176(12) 0.5620(4) 0.6801(7) 0.082(2) Uani 1 1 d . . . . .
H10 H 0.443786 0.513913 0.654697 0.098 Uiso 1 1 calc R U . . .
C11 C 0.2786(11) 0.5708(3) 0.7263(7) 0.075(2) Uani 1 1 d . . . . .
H11 H 0.212181 0.528490 0.733609 0.090 Uiso 1 1 calc R U . . .
C12 C 0.2328(9) 0.6415(3) 0.7629(6) 0.0632(15) Uani 1 1 d . . . . .
H12 H 0.135212 0.647504 0.792712 0.076 Uiso 1 1 calc R U . . .
C13 C 0.4459(8) 0.8281(3) 0.6298(5) 0.0559(14) Uani 1 1 d . . . . .
C14 C 0.2996(7) 0.8347(3) 0.6751(5) 0.0501(12) Uani 1 1 d . . . . .
C15 C 0.1704(10) 0.8836(4) 0.6154(7) 0.0754(19) Uani 1 1 d . . . . .
H15 H 0.072354 0.889034 0.644778 0.090 Uiso 1 1 calc R U . . .
C16 C 0.1869(16) 0.9259(4) 0.5088(8) 0.100(3) Uani 1 1 d . . . . .
H16 H 0.097670 0.958523 0.467117 0.121 Uiso 1 1 calc R U . . .
C17 C 0.3280(18) 0.9201(5) 0.4662(8) 0.103(3) Uani 1 1 d . . . . .
H17 H 0.336194 0.948333 0.395324 0.124 Uiso 1 1 calc R U . . .
C18 C 0.4593(12) 0.8730(4) 0.5267(6) 0.079(2) Uani 1 1 d . . . . .
H18 H 0.559304 0.870573 0.499118 0.095 Uiso 1 1 calc R U . . .
C19 C 0.1145(12) 0.7898(6) 0.8344(13) 0.117(4) Uani 1 1 d . . . . .
H19A H 0.033532 0.822075 0.775423 0.176 Uiso 1 1 calc R U . . .
H19B H 0.137432 0.810310 0.919732 0.176 Uiso 1 1 calc R U . . .
H19C H 0.066153 0.739639 0.832638 0.176 Uiso 1 1 calc R U . . .


_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 C8 1.927(6) . ?
C1 O1 1.206(8) . ?
C1 N1 1.371(8) . ?
C1 C2 1.514(9) . ?
N1 C4 1.373(7) . ?
O2 C4 1.210(7) . ?
C2 C3 1.544(7) . ?
C2 C8 1.553(8) . ?
C4 C3 1.517(7) . ?
C3 C5 1.572(7) . ?
C6 C7 1.367(9) . ?
C6 C12 1.409(8) . ?
C6 C5 1.517(7) . ?
C5 C14 1.514(8) . ?
C5 C19 1.720(10) . ?
C7 C9 1.398(8) . ?
C7 C8 1.531(9) . ?
C9 C10 1.411(12) . ?
C8 C13 1.526(9) . ?
C10 C11 1.349(12) . ?
C11 C12 1.383(10) . ?
C13 C14 1.394(9) . ?
C13 C18 1.393(9) . ?
C14 C15 1.364(9) . ?
C15 C16 1.407(13) . ?
C16 C17 1.337(15) . ?
C17 C18 1.357(14) . ?

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
O1 C1 N1 124.3(6) . . ?
O1 C1 C2 127.0(6) . . ?
N1 C1 C2 108.7(5) . . ?
C1 N1 C4 114.2(5) . . ?
C1 C2 C3 104.2(4) . . ?
C1 C2 C8 113.9(5) . . ?
C3 C2 C8 108.4(4) . . ?
O2 C4 N1 125.1(5) . . ?
O2 C4 C3 126.8(5) . . ?
N1 C4 C3 108.1(5) . . ?
C4 C3 C2 104.8(4) . . ?
C4 C3 C5 111.4(4) . . ?
C2 C3 C5 110.7(4) . . ?
C7 C6 C12 121.1(5) . . ?
C7 C6 C5 114.9(5) . . ?
C12 C6 C5 124.0(6) . . ?
C6 C5 C14 106.8(4) . . ?
C6 C5 C3 104.1(4) . . ?
C14 C5 C3 107.1(4) . . ?
C6 C5 C19 110.6(5) . . ?
C14 C5 C19 112.0(6) . . ?
C3 C5 C19 115.6(5) . . ?
C6 C7 C9 120.3(6) . . ?
C6 C7 C8 112.6(5) . . ?
C9 C7 C8 127.1(6) . . ?
C7 C9 C10 117.8(7) . . ?
C13 C8 C7 107.5(5) . . ?
C13 C8 C2 106.2(4) . . ?
C7 C8 C2 107.8(5) . . ?
C13 C8 Br1 114.1(4) . . ?
C7 C8 Br1 111.0(4) . . ?
C2 C8 Br1 109.9(4) . . ?
C11 C10 C9 121.3(6) . . ?
C10 C11 C12 121.3(7) . . ?
C11 C12 C6 118.0(7) . . ?
C14 C13 C18 119.5(6) . . ?
C14 C13 C8 112.4(5) . . ?
C18 C13 C8 128.1(7) . . ?
C15 C14 C13 119.2(6) . . ?
C15 C14 C5 126.8(6) . . ?
C13 C14 C5 114.0(5) . . ?
C14 C15 C16 119.4(8) . . ?
C17 C16 C15 121.4(8) . . ?
C16 C17 C18 119.8(8) . . ?
C17 C18 C13 120.8(9) . . ?

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
O1 C1 N1 C4 -179.2(6) . . . . ?
C2 C1 N1 C4 1.0(7) . . . . ?
O1 C1 C2 C3 -178.7(7) . . . . ?
N1 C1 C2 C3 1.2(6) . . . . ?
O1 C1 C2 C8 -60.8(9) . . . . ?
N1 C1 C2 C8 119.1(5) . . . . ?
C1 N1 C4 O2 176.4(5) . . . . ?
C1 N1 C4 C3 -2.8(6) . . . . ?
O2 C4 C3 C2 -175.8(5) . . . . ?
N1 C4 C3 C2 3.3(5) . . . . ?
O2 C4 C3 C5 64.4(7) . . . . ?
N1 C4 C3 C5 -116.4(5) . . . . ?
C1 C2 C3 C4 -2.7(5) . . . . ?
C8 C2 C3 C4 -124.3(5) . . . . ?
C1 C2 C3 C5 117.5(5) . . . . ?
C8 C2 C3 C5 -4.1(6) . . . . ?
C7 C6 C5 C14 53.6(6) . . . . ?
C12 C6 C5 C14 -125.9(6) . . . . ?
C7 C6 C5 C3 -59.6(6) . . . . ?
C12 C6 C5 C3 121.0(6) . . . . ?
C7 C6 C5 C19 175.7(6) . . . . ?
C12 C6 C5 C19 -3.8(8) . . . . ?
C4 C3 C5 C6 175.6(4) . . . . ?
C2 C3 C5 C6 59.5(5) . . . . ?
C4 C3 C5 C14 62.8(5) . . . . ?
C2 C3 C5 C14 -53.4(5) . . . . ?
C4 C3 C5 C19 -62.8(7) . . . . ?
C2 C3 C5 C19 -178.9(6) . . . . ?
C12 C6 C7 C9 0.8(8) . . . . ?
C5 C6 C7 C9 -178.7(5) . . . . ?
C12 C6 C7 C8 -180.0(5) . . . . ?
C5 C6 C7 C8 0.6(7) . . . . ?
C6 C7 C9 C10 -1.2(9) . . . . ?
C8 C7 C9 C10 179.7(6) . . . . ?
C6 C7 C8 C13 -54.6(6) . . . . ?
C9 C7 C8 C13 124.5(6) . . . . ?
C6 C7 C8 C2 59.5(6) . . . . ?
C9 C7 C8 C2 -121.3(6) . . . . ?
C6 C7 C8 Br1 179.9(4) . . . . ?
C9 C7 C8 Br1 -0.9(7) . . . . ?
C1 C2 C8 C13 -54.9(6) . . . . ?
C3 C2 C8 C13 60.6(6) . . . . ?
C1 C2 C8 C7 -169.8(5) . . . . ?
C3 C2 C8 C7 -54.4(6) . . . . ?
C1 C2 C8 Br1 69.1(5) . . . . ?
C3 C2 C8 Br1 -175.5(3) . . . . ?
C7 C9 C10 C11 0.2(10) . . . . ?
C9 C10 C11 C12 1.2(10) . . . . ?
C10 C11 C12 C6 -1.6(10) . . . . ?
C7 C6 C12 C11 0.6(9) . . . . ?
C5 C6 C12 C11 -180.0(5) . . . . ?
C7 C8 C13 C14 53.7(6) . . . . ?
C2 C8 C13 C14 -61.5(6) . . . . ?
Br1 C8 C13 C14 177.2(4) . . . . ?
C7 C8 C13 C18 -128.0(6) . . . . ?
C2 C8 C13 C18 116.8(6) . . . . ?
Br1 C8 C13 C18 -4.5(8) . . . . ?
C18 C13 C14 C15 1.6(8) . . . . ?
C8 C13 C14 C15 -179.9(5) . . . . ?
C18 C13 C14 C5 -177.7(5) . . . . ?
C8 C13 C14 C5 0.8(6) . . . . ?
C6 C5 C14 C15 126.8(6) . . . . ?
C3 C5 C14 C15 -122.2(6) . . . . ?
C19 C5 C14 C15 5.5(8) . . . . ?
C6 C5 C14 C13 -54.0(6) . . . . ?
C3 C5 C14 C13 57.1(5) . . . . ?
C19 C5 C14 C13 -175.2(5) . . . . ?
C13 C14 C15 C16 0.6(9) . . . . ?
C5 C14 C15 C16 179.7(6) . . . . ?
C14 C15 C16 C17 -1.2(11) . . . . ?
C15 C16 C17 C18 -0.3(13) . . . . ?
C16 C17 C18 C13 2.6(12) . . . . ?
C14 C13 C18 C17 -3.2(10) . . . . ?
C8 C13 C18 C17 178.6(7) . . . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -1.233
_refine_diff_density_rms         0.117

####################################################################### 
# 
# 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_t_a_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2523776'
loop_
_audit_author_name
_audit_author_address
'Guangxin Yang'
;Shanghai JiaoTong University
China
;
_audit_update_record             
;
2026-01-18 deposited with the CCDC.	2026-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H11 Br2 N O2'
_chemical_formula_sum            'C18 H11 Br2 N O2'
_chemical_formula_weight         433.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Br Br -0.6763 1.2805 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.654(3)
_cell_length_b                   7.375(2)
_cell_length_c                   17.626(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.48(2)
_cell_angle_gamma                90
_cell_volume                     1592.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6430
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      68.21

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    6.531
_shelx_estimated_absorpt_T_min   0.441
_shelx_estimated_absorpt_T_max   0.508
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21175
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.607
_diffrn_reflns_theta_max         68.594
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2920
_reflns_number_gt                2338
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+1.1261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2920
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0917
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.15665(4) 0.63854(6) 0.63685(3) 0.05423(15) Uani 1 1 d . . . . .
C1 C 0.2983(3) 0.1077(5) 0.5516(2) 0.0336(7) Uani 1 1 d . . . . .
N1 N 0.3552(3) 0.5295(4) 0.51625(19) 0.0426(7) Uani 1 1 d . . . . .
H1 H 0.384311 0.573637 0.481119 0.051 Uiso 1 1 calc R U . . .
O1 O 0.1787(2) 0.6141(4) 0.46009(16) 0.0495(7) Uani 1 1 d . . . . .
Br2 Br 0.39668(4) 0.48284(8) 0.73360(3) 0.06190(17) Uani 1 1 d . . . . .
C2 C 0.3610(3) 0.0057(5) 0.5139(2) 0.0429(9) Uani 1 1 d . . . . .
H2 H 0.428073 -0.040677 0.541294 0.051 Uiso 1 1 calc R U . . .
O2 O 0.5094(2) 0.3997(4) 0.59264(17) 0.0518(7) Uani 1 1 d . . . . .
C6 C 0.1970(3) 0.1738(5) 0.5111(2) 0.0324(7) Uani 1 1 d . . . . .
C5 C 0.1589(3) 0.1416(5) 0.4316(2) 0.0405(8) Uani 1 1 d . . . . .
H5 H 0.091556 0.186448 0.404139 0.049 Uiso 1 1 calc R U . . .
C4 C 0.2233(4) 0.0410(6) 0.3936(2) 0.0499(10) Uani 1 1 d . . . . .
H4 H 0.199033 0.019343 0.340097 0.060 Uiso 1 1 calc R U . . .
C3 C 0.3221(4) -0.0263(6) 0.4345(2) 0.0498(10) Uani 1 1 d . . . . .
H3 H 0.363718 -0.094720 0.408333 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1402(3) 0.1935(5) 0.6348(2) 0.0335(7) Uani 1 1 d . . . . .
C7 C 0.1424(2) 0.2927(5) 0.56039(18) 0.0310(7) Uani 1 1 d . . . . .
H7 H 0.069424 0.331842 0.531415 0.037 Uiso 1 1 calc R U . . .
C9 C 0.0488(3) 0.1635(5) 0.6631(2) 0.0421(8) Uani 1 1 d . . . . .
H9 H -0.019421 0.205765 0.635869 0.050 Uiso 1 1 calc R U . . .
C10 C 0.0611(3) 0.0690(6) 0.7329(3) 0.0532(11) Uani 1 1 d . . . . .
H10 H 0.000627 0.048740 0.752769 0.064 Uiso 1 1 calc R U . . .
C11 C 0.1615(4) 0.0051(6) 0.7729(2) 0.0539(11) Uani 1 1 d . . . . .
H11 H 0.167952 -0.059853 0.819077 0.065 Uiso 1 1 calc R U . . .
C12 C 0.2536(3) 0.0364(6) 0.7452(2) 0.0450(9) Uani 1 1 d . . . . .
H12 H 0.321755 -0.004872 0.772960 0.054 Uiso 1 1 calc R U . . .
C13 C 0.2417(3) 0.1294(5) 0.6761(2) 0.0345(7) Uani 1 1 d . . . . .
C14 C 0.3321(3) 0.1719(5) 0.6364(2) 0.0350(7) Uani 1 1 d . . . . .
H14 H 0.402258 0.120420 0.664744 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3368(3) 0.3812(5) 0.62984(19) 0.0341(7) Uani 1 1 d . . . . .
C16 C 0.2221(3) 0.4554(5) 0.5843(2) 0.0320(7) Uani 1 1 d . . . . .
C17 C 0.2440(3) 0.5469(5) 0.5119(2) 0.0365(8) Uani 1 1 d . . . . .
C18 C 0.4142(3) 0.4384(5) 0.5796(2) 0.0369(8) 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 C16 1.937(3) . ?
C1 C2 1.379(5) . ?
C1 C6 1.389(5) . ?
C1 C14 1.524(5) . ?
N1 C18 1.356(5) . ?
N1 C17 1.396(5) . ?
O1 C17 1.176(4) . ?
Br2 C15 1.946(3) . ?
C2 C3 1.383(6) . ?
O2 C18 1.203(4) . ?
C6 C5 1.383(5) . ?
C6 C7 1.518(5) . ?
C5 C4 1.391(5) . ?
C4 C3 1.371(6) . ?
C8 C9 1.388(5) . ?
C8 C13 1.392(5) . ?
C8 C7 1.508(5) . ?
C7 C16 1.556(5) . ?
C9 C10 1.388(6) . ?
C10 C11 1.373(7) . ?
C11 C12 1.390(6) . ?
C12 C13 1.373(5) . ?
C13 C14 1.515(4) . ?
C14 C15 1.550(5) . ?
C15 C18 1.535(5) . ?
C15 C16 1.572(4) . ?
C16 C17 1.529(5) . ?

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
C2 C1 C6 120.8(3) . . ?
C2 C1 C14 126.0(3) . . ?
C6 C1 C14 113.0(3) . . ?
C18 N1 C17 115.6(3) . . ?
C1 C2 C3 118.6(4) . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 C7 125.8(3) . . ?
C1 C6 C7 113.7(3) . . ?
C6 C5 C4 118.8(4) . . ?
C3 C4 C5 120.5(4) . . ?
C4 C3 C2 121.1(4) . . ?
C9 C8 C13 120.1(3) . . ?
C9 C8 C7 126.0(3) . . ?
C13 C8 C7 113.9(3) . . ?
C8 C7 C6 109.1(3) . . ?
C8 C7 C16 106.9(3) . . ?
C6 C7 C16 104.1(2) . . ?
C8 C9 C10 118.7(4) . . ?
C11 C10 C9 120.8(4) . . ?
C10 C11 C12 120.8(4) . . ?
C13 C12 C11 118.6(4) . . ?
C12 C13 C8 121.0(3) . . ?
C12 C13 C14 125.9(3) . . ?
C8 C13 C14 113.1(3) . . ?
C13 C14 C1 109.3(3) . . ?
C13 C14 C15 106.7(3) . . ?
C1 C14 C15 104.0(3) . . ?
C18 C15 C14 111.0(3) . . ?
C18 C15 C16 104.5(3) . . ?
C14 C15 C16 109.7(3) . . ?
C18 C15 Br2 106.4(2) . . ?
C14 C15 Br2 109.1(2) . . ?
C16 C15 Br2 116.0(2) . . ?
C17 C16 C7 110.8(3) . . ?
C17 C16 C15 104.1(3) . . ?
C7 C16 C15 108.9(3) . . ?
C17 C16 Br1 106.3(2) . . ?
C7 C16 Br1 110.0(2) . . ?
C15 C16 Br1 116.7(2) . . ?
O1 C17 N1 125.8(3) . . ?
O1 C17 C16 126.5(3) . . ?
N1 C17 C16 107.7(3) . . ?
O2 C18 N1 126.5(3) . . ?
O2 C18 C15 125.2(3) . . ?
N1 C18 C15 108.1(3) . . ?

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
C6 C1 C2 C3 1.4(5) . . . . ?
C14 C1 C2 C3 -173.8(3) . . . . ?
C2 C1 C6 C5 -1.7(5) . . . . ?
C14 C1 C6 C5 174.1(3) . . . . ?
C2 C1 C6 C7 -176.4(3) . . . . ?
C14 C1 C6 C7 -0.6(4) . . . . ?
C1 C6 C5 C4 0.6(5) . . . . ?
C7 C6 C5 C4 174.7(3) . . . . ?
C6 C5 C4 C3 0.6(6) . . . . ?
C5 C4 C3 C2 -0.9(6) . . . . ?
C1 C2 C3 C4 -0.2(6) . . . . ?
C9 C8 C7 C6 -127.1(4) . . . . ?
C13 C8 C7 C6 52.8(4) . . . . ?
C9 C8 C7 C16 120.9(4) . . . . ?
C13 C8 C7 C16 -59.2(4) . . . . ?
C5 C6 C7 C8 133.6(3) . . . . ?
C1 C6 C7 C8 -51.9(4) . . . . ?
C5 C6 C7 C16 -112.6(4) . . . . ?
C1 C6 C7 C16 61.9(4) . . . . ?
C13 C8 C9 C10 0.0(6) . . . . ?
C7 C8 C9 C10 179.9(4) . . . . ?
C8 C9 C10 C11 -0.5(6) . . . . ?
C9 C10 C11 C12 1.2(7) . . . . ?
C10 C11 C12 C13 -1.3(6) . . . . ?
C11 C12 C13 C8 0.8(6) . . . . ?
C11 C12 C13 C14 -178.5(4) . . . . ?
C9 C8 C13 C12 -0.2(6) . . . . ?
C7 C8 C13 C12 179.9(3) . . . . ?
C9 C8 C13 C14 179.2(3) . . . . ?
C7 C8 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 C1 127.3(4) . . . . ?
C8 C13 C14 C1 -52.1(4) . . . . ?
C12 C13 C14 C15 -120.8(4) . . . . ?
C8 C13 C14 C15 59.9(4) . . . . ?
C2 C1 C14 C13 -131.6(4) . . . . ?
C6 C1 C14 C13 52.8(4) . . . . ?
C2 C1 C14 C15 114.6(4) . . . . ?
C6 C1 C14 C15 -60.9(3) . . . . ?
C13 C14 C15 C18 -171.6(3) . . . . ?
C1 C14 C15 C18 -56.1(3) . . . . ?
C13 C14 C15 C16 -56.6(3) . . . . ?
C1 C14 C15 C16 58.9(3) . . . . ?
C13 C14 C15 Br2 71.5(3) . . . . ?
C1 C14 C15 Br2 -173.0(2) . . . . ?
C8 C7 C16 C17 171.0(3) . . . . ?
C6 C7 C16 C17 55.6(3) . . . . ?
C8 C7 C16 C15 57.1(3) . . . . ?
C6 C7 C16 C15 -58.3(3) . . . . ?
C8 C7 C16 Br1 -71.9(3) . . . . ?
C6 C7 C16 Br1 172.7(2) . . . . ?
C18 C15 C16 C17 0.4(3) . . . . ?
C14 C15 C16 C17 -118.7(3) . . . . ?
Br2 C15 C16 C17 117.2(3) . . . . ?
C18 C15 C16 C7 118.6(3) . . . . ?
C14 C15 C16 C7 -0.5(4) . . . . ?
Br2 C15 C16 C7 -124.6(2) . . . . ?
C18 C15 C16 Br1 -116.2(3) . . . . ?
C14 C15 C16 Br1 124.6(3) . . . . ?
Br2 C15 C16 Br1 0.5(3) . . . . ?
C18 N1 C17 O1 -176.6(4) . . . . ?
C18 N1 C17 C16 0.9(4) . . . . ?
C7 C16 C17 O1 59.8(5) . . . . ?
C15 C16 C17 O1 176.7(4) . . . . ?
Br1 C16 C17 O1 -59.6(4) . . . . ?
C7 C16 C17 N1 -117.6(3) . . . . ?
C15 C16 C17 N1 -0.8(4) . . . . ?
Br1 C16 C17 N1 123.0(3) . . . . ?
C17 N1 C18 O2 175.7(4) . . . . ?
C17 N1 C18 C15 -0.5(4) . . . . ?
C14 C15 C18 O2 -58.1(5) . . . . ?
C16 C15 C18 O2 -176.3(4) . . . . ?
Br2 C15 C18 O2 60.4(4) . . . . ?
C14 C15 C18 N1 118.2(3) . . . . ?
C16 C15 C18 N1 0.0(4) . . . . ?
Br2 C15 C18 N1 -123.2(3) . . . . ?

_refine_diff_density_max         0.624
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.070

