# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_221220e_0m
_database_code_depnum_ccdc_archive 'CCDC 2261847'
loop_
_audit_author_name
_audit_author_address
'Jin-Ming Yang'
;University
China
;
_audit_update_record             
;
2023-05-10 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_audit_creation_date             2023-02-16
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Br N O3'
_chemical_formula_sum            'C20 H14 Br N O3'
_chemical_formula_weight         396.23
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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. 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.1673(15)
_cell_length_b                   15.976(4)
_cell_length_c                   16.479(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1623.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8979
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.20
_cell_measurement_theta_min      3.35
_shelx_estimated_absorpt_T_max   0.796
_shelx_estimated_absorpt_T_min   0.763
_exptl_absorpt_coefficient_mu    2.385
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.5418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS, Madison WI for PHOTON III'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24321
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         70.461
_diffrn_reflns_theta_min         3.352
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon III 28 detector'
_diffrn_detector_area_resol_mean ' 7.39 for PHOTON III'
_diffrn_detector_type            'Bruker Photon III 28'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       'Profile data from θ/2θ scans'
_diffrn_radiation_monochromator  'Metaljet Helios MX'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_xray_symbol    'Ga K\a'
_diffrn_source                   'METALJET liquid metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_target            Ga
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                4390
_reflns_number_total             4582
_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. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_molecular_graphics    
'Bruker SHELXTL Bruker-AXS, Madison WI and local programs'
_computing_publication_material  'Bruker SHELXTL Bruker-AXS, Madison WI'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.879
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1714 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.013(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4582
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.7207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0988
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All O(H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C7(H7A,H7B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17), 
 C18(H18), C20(H20), N1(H1) 
2.c Idealised tetrahedral OH refined as rotating group: 
 O3(H3) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.38210(7) 0.72827(2) 0.34262(2) 0.03270(12) Uani 1 1 d . . . . .
C1 C -0.1513(6) 0.66062(18) 0.38065(19) 0.0259(6) Uani 1 1 d . . . . .
C2 C -0.0498(6) 0.60736(18) 0.32573(17) 0.0248(6) Uani 1 1 d . . . . .
H2 H -0.091257 0.607749 0.270205 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1137(6) 0.55313(16) 0.35258(17) 0.0231(5) Uani 1 1 d . . . . .
C4 C 0.1737(6) 0.55618(17) 0.43451(18) 0.0232(6) Uani 1 1 d . . . . .
C5 C 0.0741(6) 0.61035(19) 0.48817(18) 0.0289(7) Uani 1 1 d . . . . .
H5 H 0.119213 0.611722 0.543278 0.035 Uiso 1 1 calc R U . . .
C6 C -0.0919(7) 0.6630(2) 0.46211(19) 0.0297(7) Uani 1 1 d . . . . .
H6 H -0.162856 0.699551 0.499003 0.036 Uiso 1 1 calc R U . . .
C7 C 0.4938(6) 0.48436(19) 0.40122(18) 0.0248(6) Uani 1 1 d . . . . .
H7A H 0.602735 0.445086 0.423516 0.030 Uiso 1 1 calc R U . . .
H7B H 0.569782 0.536484 0.385524 0.030 Uiso 1 1 calc R U . . .
C8 C 0.3880(7) 0.44533(17) 0.32581(17) 0.0244(6) Uani 1 1 d . . . . .
C9 C 0.5565(6) 0.43315(19) 0.25974(18) 0.0245(6) Uani 1 1 d . . . . .
C10 C 0.5884(7) 0.49296(19) 0.19949(19) 0.0291(7) Uani 1 1 d . . . . .
H10 H 0.500204 0.541675 0.197864 0.035 Uiso 1 1 calc R U . . .
C11 C 0.7509(7) 0.4811(2) 0.1413(2) 0.0322(7) Uani 1 1 d . . . . .
H11 H 0.772603 0.521890 0.100148 0.039 Uiso 1 1 calc R U . . .
C12 C 0.8804(7) 0.4101(2) 0.14333(18) 0.0317(7) Uani 1 1 d . . . . .
H12 H 0.990615 0.402337 0.103746 0.038 Uiso 1 1 calc R U . . .
C13 C 0.8484(6) 0.3503(2) 0.20355(19) 0.0285(7) Uani 1 1 d . . . . .
H13 H 0.935881 0.301333 0.204349 0.034 Uiso 1 1 calc R U . . .
C14 C 0.6882(6) 0.36143(18) 0.26318(18) 0.0228(6) Uani 1 1 d . . . . .
C15 C 0.6412(6) 0.29874(17) 0.32593(16) 0.0230(6) Uani 1 1 d . . . . .
C16 C 0.4402(6) 0.30170(18) 0.36496(17) 0.0228(6) Uani 1 1 d . . . . .
C17 C 0.3759(6) 0.23875(18) 0.41779(17) 0.0264(6) Uani 1 1 d . . . . .
H17 H 0.237209 0.240465 0.442808 0.032 Uiso 1 1 calc R U . . .
C18 C 0.5189(6) 0.17269(18) 0.43358(18) 0.0264(6) Uani 1 1 d . . . . .
H18 H 0.476521 0.129053 0.469391 0.032 Uiso 1 1 calc R U . . .
C19 C 0.7214(6) 0.17034(19) 0.39753(19) 0.0270(6) Uani 1 1 d . . . . .
C20 C 0.7845(6) 0.23311(18) 0.34390(19) 0.0266(6) Uani 1 1 d . . . . .
H20 H 0.924142 0.231513 0.319581 0.032 Uiso 1 1 calc R U . . .
N1 N 0.2165(6) 0.49816(17) 0.29998(16) 0.0280(6) Uani 1 1 d . . . . .
H1 H 0.173928 0.495984 0.249046 0.034 Uiso 1 1 calc R U . . .
O1 O 0.3353(4) 0.50300(13) 0.46264(13) 0.0257(5) Uani 1 1 d . . . . .
O2 O 0.2921(4) 0.36492(12) 0.34873(15) 0.0258(4) Uani 1 1 d . . . . .
O3 O 0.8704(5) 0.10779(16) 0.41114(16) 0.0393(6) Uani 1 1 d . . . . .
H3 H 0.819428 0.073272 0.444523 0.059 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 C1 1.894(3) . ?
C1 C2 1.391(4) . ?
C1 C6 1.392(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(5) . ?
C3 C4 1.401(4) . ?
C3 N1 1.387(4) . ?
C4 C5 1.382(4) . ?
C4 O1 1.389(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(5) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.536(4) . ?
C7 O1 1.438(4) . ?
C8 C9 1.518(5) . ?
C8 N1 1.419(4) . ?
C8 O2 1.464(4) . ?
C9 C10 1.392(4) . ?
C9 C14 1.405(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.400(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.392(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.405(5) . ?
C14 C15 1.468(4) . ?
C15 C16 1.397(5) . ?
C15 C20 1.403(4) . ?
C16 C17 1.388(4) . ?
C16 O2 1.388(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(5) . ?
C19 C20 1.392(4) . ?
C19 O3 1.376(4) . ?
C20 H20 0.9500 . ?
N1 H1 0.8800 . ?
O3 H3 0.8400 . ?

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 Br1 118.2(2) . . ?
C2 C1 C6 121.7(3) . . ?
C6 C1 Br1 120.1(3) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 118.2(3) . . ?
N1 C3 C2 121.5(3) . . ?
N1 C3 C4 120.2(3) . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 O1 119.2(3) . . ?
O1 C4 C3 119.3(3) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
O1 C7 H7A 109.4 . . ?
O1 C7 H7B 109.4 . . ?
O1 C7 C8 111.4(3) . . ?
C9 C8 C7 110.0(3) . . ?
N1 C8 C7 108.5(2) . . ?
N1 C8 C9 111.8(2) . . ?
N1 C8 O2 107.4(3) . . ?
O2 C8 C7 108.6(2) . . ?
O2 C8 C9 110.4(2) . . ?
C10 C9 C8 121.4(3) . . ?
C10 C9 C14 120.4(3) . . ?
C14 C9 C8 118.1(3) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C15 118.1(3) . . ?
C13 C14 C9 118.8(3) . . ?
C13 C14 C15 123.0(3) . . ?
C16 C15 C14 118.4(3) . . ?
C16 C15 C20 119.1(3) . . ?
C20 C15 C14 122.3(3) . . ?
C17 C16 C15 121.2(3) . . ?
O2 C16 C15 121.3(3) . . ?
O2 C16 C17 117.4(3) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.9(3) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 120.4(3) . . ?
O3 C19 C18 123.5(3) . . ?
O3 C19 C20 116.1(3) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 C15 119.7(3) . . ?
C19 C20 H20 120.1 . . ?
C3 N1 C8 122.0(2) . . ?
C3 N1 H1 119.0 . . ?
C8 N1 H1 119.0 . . ?
C4 O1 C7 112.3(2) . . ?
C16 O2 C8 115.0(3) . . ?
C19 O3 H3 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O1 0.84 1.96 2.740(3) 154.3 2_556 yes

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
Br1 C1 C2 C3 -176.6(2) . . . . ?
Br1 C1 C6 C5 178.0(3) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
C1 C2 C3 N1 179.0(3) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 O1 179.9(3) . . . . ?
C2 C3 N1 C8 177.5(3) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C3 C4 O1 C7 31.0(4) . . . . ?
C4 C3 N1 C8 -1.9(5) . . . . ?
C4 C5 C6 C1 -1.2(5) . . . . ?
C5 C4 O1 C7 -149.7(3) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
C7 C8 C9 C10 -94.3(4) . . . . ?
C7 C8 C9 C14 82.5(3) . . . . ?
C7 C8 N1 C3 -23.6(4) . . . . ?
C7 C8 O2 C16 -71.3(3) . . . . ?
C8 C7 O1 C4 -57.4(3) . . . . ?
C8 C9 C10 C11 177.6(3) . . . . ?
C8 C9 C14 C13 -178.5(3) . . . . ?
C8 C9 C14 C15 5.7(4) . . . . ?
C9 C8 N1 C3 -145.0(3) . . . . ?
C9 C8 O2 C16 49.3(3) . . . . ?
C9 C10 C11 C12 0.0(5) . . . . ?
C9 C14 C15 C16 16.1(4) . . . . ?
C9 C14 C15 C20 -168.3(3) . . . . ?
C10 C9 C14 C13 -1.6(5) . . . . ?
C10 C9 C14 C15 -177.5(3) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 -0.9(5) . . . . ?
C12 C13 C14 C9 1.7(5) . . . . ?
C12 C13 C14 C15 177.3(3) . . . . ?
C13 C14 C15 C16 -159.5(3) . . . . ?
C13 C14 C15 C20 16.1(5) . . . . ?
C14 C9 C10 C11 0.8(5) . . . . ?
C14 C15 C16 C17 172.4(3) . . . . ?
C14 C15 C16 O2 -3.7(4) . . . . ?
C14 C15 C20 C19 -172.9(3) . . . . ?
C15 C16 C17 C18 1.9(4) . . . . ?
C15 C16 O2 C8 -30.5(4) . . . . ?
C16 C15 C20 C19 2.6(5) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C17 C16 O2 C8 153.3(3) . . . . ?
C17 C18 C19 C20 -1.0(5) . . . . ?
C17 C18 C19 O3 179.2(3) . . . . ?
C18 C19 C20 C15 -0.5(5) . . . . ?
C20 C15 C16 C17 -3.4(4) . . . . ?
C20 C15 C16 O2 -179.4(3) . . . . ?
N1 C3 C4 C5 180.0(3) . . . . ?
N1 C3 C4 O1 -0.7(5) . . . . ?
N1 C8 C9 C10 26.3(4) . . . . ?
N1 C8 C9 C14 -156.8(3) . . . . ?
N1 C8 O2 C16 171.5(2) . . . . ?
O1 C4 C5 C6 -178.5(3) . . . . ?
O1 C7 C8 C9 175.3(2) . . . . ?
O1 C7 C8 N1 52.7(3) . . . . ?
O1 C7 C8 O2 -63.7(3) . . . . ?
O2 C8 C9 C10 145.8(3) . . . . ?
O2 C8 C9 C14 -37.3(4) . . . . ?
O2 C8 N1 C3 93.7(3) . . . . ?
O2 C16 C17 C18 178.1(3) . . . . ?
O3 C19 C20 C15 179.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_124311
_database_code_depnum_ccdc_archive 'CCDC 2283919'
loop_
_audit_author_name
_audit_author_address
'Jin-Ming Yang'
;University
China
;
_audit_update_record             
;
2023-07-24 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_audit_creation_date             2023-07-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 Br N O3'
_chemical_formula_sum            'C23 H16 Br N O3'
_chemical_formula_weight         434.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.11122(19)
_cell_length_b                   11.90270(16)
_cell_length_c                   26.9246(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.0778(14)
_cell_angle_gamma                90
_cell_volume                     4366.61(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    19341
_cell_measurement_temperature    99.97(14)
_cell_measurement_theta_max      73.8230
_cell_measurement_theta_min      3.2340
_shelx_estimated_absorpt_T_max   0.811
_shelx_estimated_absorpt_T_min   0.700
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22661
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         3.244
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  29.00   0.50    0.50    --    0.00 -82.00 120.00  120
  2  ω    -79.00 -30.00   0.50    0.50    --    0.00 -57.00-120.00   98
  3  ω      6.00 114.00   0.50    0.50    --   95.80 -45.00  90.00  216
  4  ω     87.00 127.00   0.50    0.50    --   95.80 -82.00-120.00   80
  5  ω     24.00 122.00   0.50    0.50    --   95.80 -82.00-180.00  196
  6  ω    104.00 129.00   0.50    0.50    --   95.80  82.00 120.00   50
  7  ω     20.00 100.00   0.50    0.50    --   95.80 -45.00   0.00  160
  8  ω    -44.00   8.00   0.50    0.50    --    0.00 -77.00-120.00  104
  9  ω     87.00 114.00   0.50    0.50    --   95.80 -82.00-150.00   54
 10  ω    110.00 136.00   0.50    0.50    --   95.80  30.00 -90.00   52
 11  ω     20.00  58.00   0.50    0.50    --   95.80 -82.00-150.00   76
 12  ω    -88.00 -61.00   0.50    0.50    --    0.00 -38.00 -60.00   54
 13  ω      5.00  31.00   0.50    0.50    --    0.00 -82.00  90.00   52
 14  ω    -24.00   2.00   0.50    0.50    --    0.00 -82.00-150.00   52
 15  ω    -42.00 -16.00   0.50    0.50    --    0.00 -38.00 -60.00   52
 16  ω    -31.00  -5.00   0.50    0.50    --    0.00 -82.00-180.00   52
 17  ω    -28.00  -3.00   0.50    0.50    --    0.00 -82.00  90.00   50
 18  ω    125.00 179.00   0.50    0.50    --   95.80  45.00-180.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0060943000
_diffrn_orient_matrix_UB_12      0.0306367000
_diffrn_orient_matrix_UB_13      -0.0563262000
_diffrn_orient_matrix_UB_21      -0.1128600000
_diffrn_orient_matrix_UB_22      -0.0069403000
_diffrn_orient_matrix_UB_23      -0.0129454000
_diffrn_orient_matrix_UB_31      -0.0047047000
_diffrn_orient_matrix_UB_32      0.1254986000
_diffrn_orient_matrix_UB_33      0.0130548000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6477
_reflns_number_total             7498
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL n/a (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+4.4237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0922
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C23(H23A,H23B), C30(H30A,H30B), C46(H46A,H46B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C17(H17),
 C18(H18), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28), C33(H33),
  C34(H34), C36(H36), C40(H40), C41(H41), C44(H44), C45(H45)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.18147(2) 0.16795(3) 0.89946(2) 0.03521(9) Uani 1 1 d . . . . .
O1 O 0.35066(12) 0.05332(15) 0.63041(6) 0.0252(4) Uani 1 1 d . . . . .
O2 O 0.35480(12) 0.24967(14) 0.69132(6) 0.0226(4) Uani 1 1 d . . . . .
O3 O 0.68882(12) 0.25746(16) 0.85184(7) 0.0299(4) Uani 1 1 d . . . . .
N1 N 0.19861(16) 0.18568(19) 0.64921(8) 0.0229(5) Uani 1 1 d . . . . .
H1 H 0.169(2) 0.243(3) 0.6530(10) 0.028(8) Uiso 1 1 d . . . . .
C1 C 0.27541(18) 0.0920(2) 0.59003(9) 0.0237(6) Uani 1 1 d . . . . .
C2 C 0.2789(2) 0.0649(2) 0.54046(10) 0.0315(6) Uani 1 1 d . . . . .
H2 H 0.331110 0.020351 0.534992 0.038 Uiso 1 1 calc R U . . .
C3 C 0.2061(2) 0.1029(3) 0.49907(11) 0.0370(7) Uani 1 1 d . . . . .
H3 H 0.207925 0.084246 0.465024 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1304(2) 0.1681(2) 0.50729(10) 0.0326(6) Uani 1 1 d . . . . .
H4 H 0.079967 0.193587 0.478781 0.039 Uiso 1 1 calc R U . . .
C5 C 0.12756(19) 0.1966(2) 0.55670(10) 0.0265(6) Uani 1 1 d . . . . .
H5 H 0.075566 0.241861 0.561934 0.032 Uiso 1 1 calc R U . . .
C6 C 0.20071(18) 0.1591(2) 0.59882(9) 0.0219(5) Uani 1 1 d . . . . .
C7 C 0.32473(18) 0.0489(2) 0.67831(9) 0.0223(5) Uani 1 1 d . . . . .
H7A H 0.383736 0.030832 0.706256 0.027 Uiso 1 1 calc R U . . .
H7B H 0.275978 -0.011574 0.676941 0.027 Uiso 1 1 calc R U . . .
C8 C 0.28178(18) 0.1607(2) 0.69014(9) 0.0220(5) Uani 1 1 d . . . . .
C9 C 0.25755(18) 0.1572(2) 0.74142(9) 0.0212(5) Uani 1 1 d . . . . .
C10 C 0.16299(18) 0.1315(2) 0.74465(10) 0.0240(5) Uani 1 1 d . . . . .
H10 H 0.113629 0.114092 0.714230 0.029 Uiso 1 1 calc R U . . .
C11 C 0.14004(19) 0.1312(2) 0.79157(10) 0.0256(6) Uani 1 1 d . . . . .
H11 H 0.075794 0.112608 0.793798 0.031 Uiso 1 1 calc R U . . .
C12 C 0.21284(19) 0.1584(2) 0.83510(10) 0.0249(6) Uani 1 1 d . . . . .
C13 C 0.30776(18) 0.1826(2) 0.83323(10) 0.0229(5) Uani 1 1 d . . . . .
H13 H 0.356093 0.201646 0.863821 0.027 Uiso 1 1 calc R U . . .
C14 C 0.33226(18) 0.1790(2) 0.78626(10) 0.0214(5) Uani 1 1 d . . . . .
C15 C 0.43080(18) 0.2081(2) 0.78069(9) 0.0202(5) Uani 1 1 d . . . . .
C16 C 0.43695(18) 0.2470(2) 0.73269(9) 0.0217(5) Uani 1 1 d . . . . .
C17 C 0.52326(18) 0.2893(2) 0.72468(10) 0.0243(5) Uani 1 1 d . . . . .
H17 H 0.525267 0.314483 0.691489 0.029 Uiso 1 1 calc R U . . .
C18 C 0.60649(19) 0.2946(2) 0.76535(10) 0.0260(6) Uani 1 1 d . . . . .
H18 H 0.665633 0.325205 0.760525 0.031 Uiso 1 1 calc R U . . .
C19 C 0.60283(18) 0.2549(2) 0.81310(10) 0.0244(6) Uani 1 1 d . . . . .
C20 C 0.51769(18) 0.2066(2) 0.82135(10) 0.0226(5) Uani 1 1 d . . . . .
C21 C 0.52839(19) 0.1485(2) 0.87033(10) 0.0271(6) Uani 1 1 d . . . . .
H21 H 0.481268 0.094298 0.873987 0.032 Uiso 1 1 calc R U . . .
C22 C 0.60440(19) 0.1722(2) 0.90963(10) 0.0313(6) Uani 1 1 d . . . . .
H22 H 0.613625 0.133578 0.941422 0.038 Uiso 1 1 calc R U . . .
C23 C 0.6751(2) 0.2604(3) 0.90299(10) 0.0333(7) Uani 1 1 d . . . . .
H23A H 0.650196 0.335278 0.909476 0.040 Uiso 1 1 calc R U . . .
H23B H 0.739023 0.248423 0.928404 0.040 Uiso 1 1 calc R U . . .
Br2 Br 0.42957(2) 0.43424(3) 0.93013(2) 0.04142(10) Uani 1 1 d . . . . .
O4 O 0.08697(14) 0.59914(16) 0.63743(8) 0.0359(5) Uani 1 1 d . . . . .
O5 O 0.12940(12) 0.39648(14) 0.69357(7) 0.0242(4) Uani 1 1 d . . . . .
O6 O -0.12600(12) 0.38084(15) 0.81706(7) 0.0271(4) Uani 1 1 d . . . . .
N2 N 0.26157(15) 0.47102(18) 0.66900(8) 0.0253(5) Uani 1 1 d . . . . .
H2A H 0.317478 0.503959 0.679402 0.030 Uiso 1 1 d R U . . .
C24 C 0.1329(2) 0.5583(2) 0.60209(11) 0.0355(7) Uani 1 1 d . . . . .
C25 C 0.0904(3) 0.5809(3) 0.55048(13) 0.0493(9) Uani 1 1 d . . . . .
H25 H 0.032867 0.625771 0.540702 0.059 Uiso 1 1 calc R U . . .
C26 C 0.1323(3) 0.5379(3) 0.51330(13) 0.0574(11) Uani 1 1 d . . . . .
H26 H 0.103483 0.553758 0.478010 0.069 Uiso 1 1 calc R U . . .
C27 C 0.2152(3) 0.4726(3) 0.52724(12) 0.0512(10) Uani 1 1 d . . . . .
H27 H 0.243402 0.443251 0.501556 0.061 Uiso 1 1 calc R U . . .
C28 C 0.2578(2) 0.4492(3) 0.57873(11) 0.0371(7) Uani 1 1 d . . . . .
H28 H 0.314785 0.403317 0.588110 0.045 Uiso 1 1 calc R U . . .
C29 C 0.2176(2) 0.4927(2) 0.61660(10) 0.0292(6) Uani 1 1 d . . . . .
C30 C 0.1468(2) 0.6002(2) 0.68894(10) 0.0290(6) Uani 1 1 d . . . . .
H30A H 0.105091 0.614086 0.712736 0.035 Uiso 1 1 calc R U . . .
H30B H 0.194805 0.662399 0.693030 0.035 Uiso 1 1 calc R U . . .
C31 C 0.20171(18) 0.4892(2) 0.70311(10) 0.0230(5) Uani 1 1 d . . . . .
C32 C 0.25823(18) 0.4852(2) 0.75882(10) 0.0234(5) Uani 1 1 d . . . . .
C33 C 0.35857(19) 0.5070(2) 0.77438(10) 0.0271(6) Uani 1 1 d . . . . .
H33 H 0.392219 0.528994 0.749633 0.033 Uiso 1 1 calc R U . . .
C34 C 0.4099(2) 0.4969(2) 0.82566(10) 0.0301(6) Uani 1 1 d . . . . .
H34 H 0.478229 0.512488 0.836425 0.036 Uiso 1 1 calc R U . . .
C35 C 0.3592(2) 0.4636(2) 0.86066(10) 0.0306(6) Uani 1 1 d . . . . .
C36 C 0.25894(19) 0.4440(2) 0.84651(10) 0.0259(6) Uani 1 1 d . . . . .
H36 H 0.226055 0.421622 0.871521 0.031 Uiso 1 1 calc R U . . .
C37 C 0.20662(18) 0.4576(2) 0.79515(10) 0.0229(5) Uani 1 1 d . . . . .
C38 C 0.10149(18) 0.4292(2) 0.77681(10) 0.0229(5) Uani 1 1 d . . . . .
C39 C 0.06828(18) 0.3932(2) 0.72608(10) 0.0224(5) Uani 1 1 d . . . . .
C40 C -0.02499(19) 0.3484(2) 0.70695(10) 0.0265(6) Uani 1 1 d . . . . .
H40 H -0.045675 0.323315 0.672307 0.032 Uiso 1 1 calc R U . . .
C41 C -0.08733(19) 0.3407(2) 0.73868(10) 0.0266(6) Uani 1 1 d . . . . .
H41 H -0.150360 0.307618 0.726300 0.032 Uiso 1 1 calc R U . . .
C42 C -0.05800(18) 0.3811(2) 0.78867(10) 0.0239(5) Uani 1 1 d . . . . .
C43 C 0.03462(18) 0.4298(2) 0.80800(10) 0.0231(5) Uani 1 1 d . . . . .
C44 C 0.05081(19) 0.4891(2) 0.85719(10) 0.0257(6) Uani 1 1 d . . . . .
H44 H 0.103157 0.541418 0.867287 0.031 Uiso 1 1 calc R U . . .
C45 C -0.00803(19) 0.4696(2) 0.88767(10) 0.0255(6) Uani 1 1 d . . . . .
H45 H -0.001185 0.510916 0.918589 0.031 Uiso 1 1 calc R U . . .
C46 C -0.08516(19) 0.3810(2) 0.87207(10) 0.0284(6) Uani 1 1 d . . . . .
H46A H -0.056139 0.306470 0.883201 0.034 Uiso 1 1 calc R U . . .
H46B H -0.138044 0.394812 0.889316 0.034 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 C12 1.900(3) . ?
O1 C1 1.386(3) . ?
O1 C7 1.430(3) . ?
O2 C8 1.472(3) . ?
O2 C16 1.383(3) . ?
O3 C19 1.379(3) . ?
O3 C23 1.440(3) . ?
N1 H1 0.82(3) . ?
N1 C6 1.401(3) . ?
N1 C8 1.417(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.391(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.530(3) . ?
C8 C9 1.507(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.405(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(4) . ?
C12 C13 1.384(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(3) . ?
C14 C15 1.478(3) . ?
C15 C16 1.397(3) . ?
C15 C20 1.416(3) . ?
C16 C17 1.386(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(4) . ?
C19 C20 1.401(4) . ?
C20 C21 1.462(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.326(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.492(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
Br2 C35 1.908(3) . ?
O4 C24 1.372(4) . ?
O4 C30 1.424(3) . ?
O5 C31 1.479(3) . ?
O5 C39 1.380(3) . ?
O6 C42 1.373(3) . ?
O6 C46 1.443(3) . ?
N2 H2A 0.8600 . ?
N2 C29 1.410(3) . ?
N2 C31 1.417(3) . ?
C24 C25 1.389(4) . ?
C24 C29 1.396(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.373(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.388(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.389(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.529(4) . ?
C31 C32 1.505(3) . ?
C32 C33 1.392(4) . ?
C32 C37 1.402(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.388(4) . ?
C34 H34 0.9500 . ?
C34 C35 1.381(4) . ?
C35 C36 1.387(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.397(4) . ?
C37 C38 1.476(3) . ?
C38 C39 1.392(3) . ?
C38 C43 1.417(3) . ?
C39 C40 1.389(4) . ?
C40 H40 0.9500 . ?
C40 C41 1.380(4) . ?
C41 H41 0.9500 . ?
C41 C42 1.387(4) . ?
C42 C43 1.400(4) . ?
C43 C44 1.465(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.331(4) . ?
C45 H45 0.9500 . ?
C45 C46 1.495(4) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?

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 C7 113.32(18) . . ?
C16 O2 C8 115.88(18) . . ?
C19 O3 C23 114.41(19) . . ?
C6 N1 H1 117(2) . . ?
C6 N1 C8 118.9(2) . . ?
C8 N1 H1 115(2) . . ?
O1 C1 C6 121.1(2) . . ?
C2 C1 O1 117.8(2) . . ?
C2 C1 C6 121.0(2) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 N1 120.2(2) . . ?
C1 C6 C5 118.6(2) . . ?
C5 C6 N1 121.2(2) . . ?
O1 C7 H7A 109.4 . . ?
O1 C7 H7B 109.4 . . ?
O1 C7 C8 111.4(2) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
O2 C8 C7 108.49(19) . . ?
O2 C8 C9 108.95(19) . . ?
N1 C8 O2 107.4(2) . . ?
N1 C8 C7 108.3(2) . . ?
N1 C8 C9 112.3(2) . . ?
C9 C8 C7 111.3(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 C14 120.2(2) . . ?
C14 C9 C8 118.9(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.4(2) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 Br1 119.31(19) . . ?
C11 C12 C13 122.1(2) . . ?
C13 C12 Br1 118.56(19) . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C15 118.1(2) . . ?
C13 C14 C9 118.5(2) . . ?
C13 C14 C15 123.1(2) . . ?
C16 C15 C14 117.3(2) . . ?
C16 C15 C20 118.0(2) . . ?
C20 C15 C14 124.6(2) . . ?
O2 C16 C15 120.8(2) . . ?
O2 C16 C17 116.9(2) . . ?
C17 C16 C15 122.2(2) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.5(2) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.4(2) . . ?
C19 C18 H18 120.3 . . ?
O3 C19 C18 117.2(2) . . ?
O3 C19 C20 120.8(2) . . ?
C18 C19 C20 121.9(2) . . ?
C15 C20 C21 124.7(2) . . ?
C19 C20 C15 118.6(2) . . ?
C19 C20 C21 116.5(2) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 120.6 . . ?
C21 C22 C23 118.8(3) . . ?
C23 C22 H22 120.6 . . ?
O3 C23 C22 111.0(2) . . ?
O3 C23 H23A 109.4 . . ?
O3 C23 H23B 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C24 O4 C30 114.3(2) . . ?
C39 O5 C31 115.32(18) . . ?
C42 O6 C46 114.89(19) . . ?
C29 N2 H2A 111.7 . . ?
C29 N2 C31 116.1(2) . . ?
C31 N2 H2A 111.7 . . ?
O4 C24 C25 117.8(3) . . ?
O4 C24 C29 121.9(3) . . ?
C25 C24 C29 120.3(3) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.8(3) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.3(3) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.9 . . ?
C27 C28 C29 120.3(3) . . ?
C29 C28 H28 119.9 . . ?
C24 C29 N2 120.3(3) . . ?
C28 C29 N2 120.6(3) . . ?
C28 C29 C24 119.1(3) . . ?
O4 C30 H30A 109.3 . . ?
O4 C30 H30B 109.3 . . ?
O4 C30 C31 111.6(2) . . ?
H30A C30 H30B 108.0 . . ?
C31 C30 H30A 109.3 . . ?
C31 C30 H30B 109.3 . . ?
O5 C31 C30 108.6(2) . . ?
O5 C31 C32 108.21(19) . . ?
N2 C31 O5 105.90(19) . . ?
N2 C31 C30 108.6(2) . . ?
N2 C31 C32 113.0(2) . . ?
C32 C31 C30 112.2(2) . . ?
C33 C32 C31 121.9(2) . . ?
C33 C32 C37 120.4(2) . . ?
C37 C32 C31 117.8(2) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 C32 120.7(2) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 H34 120.8 . . ?
C35 C34 C33 118.4(2) . . ?
C35 C34 H34 120.8 . . ?
C34 C35 Br2 119.5(2) . . ?
C34 C35 C36 122.2(3) . . ?
C36 C35 Br2 118.2(2) . . ?
C35 C36 H36 120.3 . . ?
C35 C36 C37 119.4(2) . . ?
C37 C36 H36 120.3 . . ?
C32 C37 C38 118.7(2) . . ?
C36 C37 C32 118.7(2) . . ?
C36 C37 C38 122.1(2) . . ?
C39 C38 C37 116.8(2) . . ?
C39 C38 C43 118.5(2) . . ?
C43 C38 C37 124.6(2) . . ?
O5 C39 C38 120.5(2) . . ?
O5 C39 C40 117.6(2) . . ?
C40 C39 C38 121.8(2) . . ?
C39 C40 H40 120.3 . . ?
C41 C40 C39 119.4(2) . . ?
C41 C40 H40 120.3 . . ?
C40 C41 H41 120.0 . . ?
C40 C41 C42 120.0(2) . . ?
C42 C41 H41 120.0 . . ?
O6 C42 C41 117.6(2) . . ?
O6 C42 C43 120.9(2) . . ?
C41 C42 C43 121.2(2) . . ?
C38 C43 C44 124.5(2) . . ?
C42 C43 C38 118.6(2) . . ?
C42 C43 C44 116.5(2) . . ?
C43 C44 H44 120.1 . . ?
C45 C44 C43 119.8(2) . . ?
C45 C44 H44 120.1 . . ?
C44 C45 H45 120.8 . . ?
C44 C45 C46 118.4(2) . . ?
C46 C45 H45 120.8 . . ?
O6 C46 C45 110.9(2) . . ?
O6 C46 H46A 109.5 . . ?
O6 C46 H46B 109.5 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 108.1 . . ?

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
Br1 C12 C13 C14 -178.40(19) . . . . ?
O1 C1 C2 C3 -179.2(2) . . . . ?
O1 C1 C6 N1 -2.2(4) . . . . ?
O1 C1 C6 C5 179.3(2) . . . . ?
O1 C7 C8 O2 -58.3(2) . . . . ?
O1 C7 C8 N1 58.0(3) . . . . ?
O1 C7 C8 C9 -178.15(19) . . . . ?
O2 C8 C9 C10 145.1(2) . . . . ?
O2 C8 C9 C14 -35.6(3) . . . . ?
O2 C16 C17 C18 176.5(2) . . . . ?
O3 C19 C20 C15 178.8(2) . . . . ?
O3 C19 C20 C21 -6.9(4) . . . . ?
N1 C8 C9 C10 26.2(3) . . . . ?
N1 C8 C9 C14 -154.5(2) . . . . ?
C1 O1 C7 C8 -51.4(3) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C1 C6 N1 -179.9(2) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 N1 -179.2(2) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C6 N1 C8 O2 79.5(3) . . . . ?
C6 N1 C8 C7 -37.5(3) . . . . ?
C6 N1 C8 C9 -160.8(2) . . . . ?
C6 C1 C2 C3 -1.4(4) . . . . ?
C7 O1 C1 C2 -158.6(2) . . . . ?
C7 O1 C1 C6 23.6(3) . . . . ?
C7 C8 C9 C10 -95.3(3) . . . . ?
C7 C8 C9 C14 84.0(3) . . . . ?
C8 O2 C16 C15 -32.2(3) . . . . ?
C8 O2 C16 C17 150.6(2) . . . . ?
C8 N1 C6 C1 11.2(4) . . . . ?
C8 N1 C6 C5 -170.3(2) . . . . ?
C8 C9 C10 C11 -178.3(2) . . . . ?
C8 C9 C14 C13 176.0(2) . . . . ?
C8 C9 C14 C15 1.9(3) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C9 C14 C15 C16 20.1(3) . . . . ?
C9 C14 C15 C20 -164.6(2) . . . . ?
C10 C9 C14 C13 -4.7(4) . . . . ?
C10 C9 C14 C15 -178.8(2) . . . . ?
C10 C11 C12 Br1 176.02(19) . . . . ?
C10 C11 C12 C13 -1.9(4) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C9 3.7(4) . . . . ?
C12 C13 C14 C15 177.5(2) . . . . ?
C13 C14 C15 C16 -153.7(2) . . . . ?
C13 C14 C15 C20 21.6(4) . . . . ?
C14 C9 C10 C11 2.4(4) . . . . ?
C14 C15 C16 O2 -4.9(3) . . . . ?
C14 C15 C16 C17 172.1(2) . . . . ?
C14 C15 C20 C19 -168.7(2) . . . . ?
C14 C15 C20 C21 17.5(4) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C15 C20 C21 C22 -165.3(3) . . . . ?
C16 O2 C8 N1 172.67(19) . . . . ?
C16 O2 C8 C7 -70.5(2) . . . . ?
C16 O2 C8 C9 50.8(3) . . . . ?
C16 C15 C20 C19 6.6(4) . . . . ?
C16 C15 C20 C21 -167.2(2) . . . . ?
C16 C17 C18 C19 1.6(4) . . . . ?
C17 C18 C19 O3 177.2(2) . . . . ?
C17 C18 C19 C20 1.7(4) . . . . ?
C18 C19 C20 C15 -5.9(4) . . . . ?
C18 C19 C20 C21 168.5(2) . . . . ?
C19 O3 C23 C22 49.1(3) . . . . ?
C19 C20 C21 C22 20.7(4) . . . . ?
C20 C15 C16 O2 179.5(2) . . . . ?
C20 C15 C16 C17 -3.5(4) . . . . ?
C20 C21 C22 C23 2.0(4) . . . . ?
C21 C22 C23 O3 -36.4(4) . . . . ?
C23 O3 C19 C18 155.7(2) . . . . ?
C23 O3 C19 C20 -28.7(3) . . . . ?
Br2 C35 C36 C37 -175.76(19) . . . . ?
O4 C24 C25 C26 -177.7(3) . . . . ?
O4 C24 C29 N2 -3.1(4) . . . . ?
O4 C24 C29 C28 176.8(2) . . . . ?
O4 C30 C31 O5 -55.3(3) . . . . ?
O4 C30 C31 N2 59.4(3) . . . . ?
O4 C30 C31 C32 -174.9(2) . . . . ?
O5 C31 C32 C33 141.1(2) . . . . ?
O5 C31 C32 C37 -38.3(3) . . . . ?
O5 C39 C40 C41 178.2(2) . . . . ?
O6 C42 C43 C38 -179.1(2) . . . . ?
O6 C42 C43 C44 -5.8(4) . . . . ?
N2 C31 C32 C33 24.1(3) . . . . ?
N2 C31 C32 C37 -155.3(2) . . . . ?
C24 O4 C30 C31 -46.3(3) . . . . ?
C24 C25 C26 C27 0.4(5) . . . . ?
C25 C24 C29 N2 179.1(3) . . . . ?
C25 C24 C29 C28 -1.0(4) . . . . ?
C25 C26 C27 C28 -0.1(5) . . . . ?
C26 C27 C28 C29 -0.7(4) . . . . ?
C27 C28 C29 N2 -178.9(2) . . . . ?
C27 C28 C29 C24 1.2(4) . . . . ?
C29 N2 C31 O5 72.4(3) . . . . ?
C29 N2 C31 C30 -44.1(3) . . . . ?
C29 N2 C31 C32 -169.4(2) . . . . ?
C29 C24 C25 C26 0.2(4) . . . . ?
C30 O4 C24 C25 -163.5(2) . . . . ?
C30 O4 C24 C29 18.7(4) . . . . ?
C30 C31 C32 C33 -99.1(3) . . . . ?
C30 C31 C32 C37 81.5(3) . . . . ?
C31 O5 C39 C38 -32.3(3) . . . . ?
C31 O5 C39 C40 150.4(2) . . . . ?
C31 N2 C29 C24 18.0(3) . . . . ?
C31 N2 C29 C28 -161.9(2) . . . . ?
C31 C32 C33 C34 -176.5(2) . . . . ?
C31 C32 C37 C36 174.6(2) . . . . ?
C31 C32 C37 C38 2.6(3) . . . . ?
C32 C33 C34 C35 0.7(4) . . . . ?
C32 C37 C38 C39 22.1(3) . . . . ?
C32 C37 C38 C43 -161.9(2) . . . . ?
C33 C32 C37 C36 -4.8(4) . . . . ?
C33 C32 C37 C38 -176.8(2) . . . . ?
C33 C34 C35 Br2 173.8(2) . . . . ?
C33 C34 C35 C36 -2.3(4) . . . . ?
C34 C35 C36 C37 0.4(4) . . . . ?
C35 C36 C37 C32 3.2(4) . . . . ?
C35 C36 C37 C38 174.9(2) . . . . ?
C36 C37 C38 C39 -149.6(2) . . . . ?
C36 C37 C38 C43 26.3(4) . . . . ?
C37 C32 C33 C34 2.9(4) . . . . ?
C37 C38 C39 O5 -7.0(3) . . . . ?
C37 C38 C39 C40 170.2(2) . . . . ?
C37 C38 C43 C42 -168.0(2) . . . . ?
C37 C38 C43 C44 19.3(4) . . . . ?
C38 C39 C40 C41 0.9(4) . . . . ?
C38 C43 C44 C45 -168.8(3) . . . . ?
C39 O5 C31 N2 175.0(2) . . . . ?
C39 O5 C31 C30 -68.5(3) . . . . ?
C39 O5 C31 C32 53.6(3) . . . . ?
C39 C38 C43 C42 7.9(4) . . . . ?
C39 C38 C43 C44 -164.8(2) . . . . ?
C39 C40 C41 C42 2.3(4) . . . . ?
C40 C41 C42 O6 174.1(2) . . . . ?
C40 C41 C42 C43 -0.3(4) . . . . ?
C41 C42 C43 C38 -4.9(4) . . . . ?
C41 C42 C43 C44 168.4(2) . . . . ?
C42 O6 C46 C45 48.8(3) . . . . ?
C42 C43 C44 C45 18.4(4) . . . . ?
C43 C38 C39 O5 176.8(2) . . . . ?
C43 C38 C39 C40 -6.1(4) . . . . ?
C43 C44 C45 C46 4.2(4) . . . . ?
C44 C45 C46 O6 -37.1(3) . . . . ?
C46 O6 C42 C41 157.0(2) . . . . ?
C46 O6 C42 C43 -28.6(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.500 0.500 0.500 514.8 104.1 ?
2 -0.500 0.000 0.000 514.8 104.1 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.936
_oxdiff_exptl_absorpt_empirical_full_min 0.643
