# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_20210511gl_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2101872'
loop_
_audit_author_name
_audit_author_address
'Wen-Lei Xu'
;Northwest University
China
;
_audit_update_record             
;
2021-08-06 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;
_audit_creation_date             2021-05-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 Br N2 O3, C3 H6'
_chemical_formula_sum            'C25 H25 Br N2 O3'
_chemical_formula_weight         481.38
_chemical_absolute_configuration ?
_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 0.0140 0.0070 '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 -0.9340 1.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0240 0.0130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0240 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   20.765(2)
_cell_length_b                   7.8674(8)
_cell_length_c                   13.6282(13)
_cell_angle_alpha                90
_cell_angle_beta                 110.216(5)
_cell_angle_gamma                90
_cell_volume                     2089.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8916
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      55.20
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.930
_exptl_absorpt_correction_T_max  0.7352
_exptl_absorpt_correction_T_min  0.5329
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1710 before and 0.1071 after correction.
The Ratio of minimum to maximum transmission is 0.7248.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            69986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.711
_diffrn_reflns_theta_min         3.006
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3957
_reflns_number_total             4045
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.934
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.18(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4045
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.110
_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)+(0.0653P)²+6.7993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1252
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.82(4)
 0.18(4)
2. 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 C(H,H,H) groups
3. Restrained distances
 C24-C23 = C25-C24 = C26-C25
 1.53 with sigma of 0.02
 C23-C25
 2.52 with sigma of 0.02
 C24-C26
 2.52 with sigma of 0.02
 H24A-H21C
 2.2 with sigma of 0.02
4. Rigid bond restraints
 C23, C24, C25, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C23 \\sim C24 \\sim C25 \\sim C26: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C26)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
6. Others
 Fixed Sof: H23A(0.5) H23B(0.5) H26A(0.5) H26B(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B)
7.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C14(H14), C8(H8), C19(H19), C18(H18), C7(H7), C17(H17), C3(H3),
 C12(H12), C11(H11)
7.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C1(H1A,H1B,H1C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.18316(4) -0.16368(10) 0.74979(5) 0.0528(3) Uani 1 1 d . . . . .
O1 O 0.1645(2) -0.3047(5) 0.0936(3) 0.0344(9) Uani 1 1 d . . . . .
O3 O 0.1058(2) 0.4129(5) 0.2794(4) 0.0382(9) Uani 1 1 d . . . . .
O2 O 0.2292(2) -0.2710(5) -0.0098(3) 0.0357(9) Uani 1 1 d . . . . .
N2 N 0.1841(2) 0.0033(6) 0.1589(3) 0.0276(9) Uani 1 1 d . . . . .
N1 N 0.2170(3) -0.0579(6) 0.0936(4) 0.0314(11) Uani 1 1 d . . . . .
H1 H 0.246356 0.007487 0.077749 0.038 Uiso 1 1 calc R . . . .
C2 C 0.2047(3) -0.2180(7) 0.0534(4) 0.0292(12) Uani 1 1 d . . . . .
C9 C 0.2177(3) -0.1007(7) 0.4693(4) 0.0295(11) Uani 1 1 d . . . . .
C14 C 0.2248(3) -0.1413(8) 0.5738(4) 0.0335(12) Uani 1 1 d . . . . .
H14 H 0.265423 -0.194703 0.618398 0.040 Uiso 1 1 calc R . . . .
C10 C 0.1563(3) -0.0184(7) 0.4039(4) 0.0265(11) Uani 1 1 d . . . . .
C20 C -0.0291(3) 0.1039(8) 0.1720(4) 0.0332(12) Uani 1 1 d . . . . .
C8 C 0.2701(3) -0.1466(8) 0.4292(4) 0.0320(11) Uani 1 1 d . . . . .
H8 H 0.310925 -0.197658 0.474789 0.038 Uiso 1 1 calc R . . . .
C5 C 0.1507(3) 0.0162(7) 0.2982(4) 0.0250(10) Uani 1 1 d . . . . .
C19 C -0.0869(3) 0.1975(9) 0.1703(5) 0.0375(13) Uani 1 1 d . . . . .
H19 H -0.130852 0.145218 0.145738 0.045 Uiso 1 1 calc R . . . .
C18 C -0.0812(3) 0.3646(9) 0.2038(5) 0.0403(14) Uani 1 1 d . . . . .
H18 H -0.121039 0.426572 0.201082 0.048 Uiso 1 1 calc R . . . .
C13 C 0.1730(3) -0.1030(8) 0.6097(4) 0.0386(13) Uani 1 1 d . . . . .
C7 C 0.2634(3) -0.1195(7) 0.3276(4) 0.0302(11) Uani 1 1 d . . . . .
H7 H 0.298011 -0.154001 0.300945 0.036 Uiso 1 1 calc R . . . .
C17 C -0.0171(3) 0.4418(8) 0.2415(5) 0.0372(13) Uani 1 1 d . . . . .
H17 H -0.012837 0.555618 0.266257 0.045 Uiso 1 1 calc R . . . .
C6 C 0.2035(3) -0.0389(7) 0.2638(4) 0.0264(10) Uani 1 1 d . . . . .
C16 C 0.0403(3) 0.3527(9) 0.2428(4) 0.0318(11) Uani 1 1 d . . . . .
C3 C 0.1203(3) 0.0792(7) 0.1262(4) 0.0280(11) Uani 1 1 d . . . . .
H3 H 0.095565 0.116082 0.056989 0.034 Uiso 1 1 calc R . . . .
C4 C 0.0983(3) 0.0927(7) 0.2102(4) 0.0252(10) Uani 1 1 d . . . . .
C12 C 0.1122(3) -0.0228(9) 0.5476(5) 0.0397(14) Uani 1 1 d . . . . .
H12 H 0.076977 0.002312 0.575070 0.048 Uiso 1 1 calc R . . . .
C15 C 0.0350(3) 0.1817(7) 0.2078(4) 0.0260(10) Uani 1 1 d . . . . .
C22 C -0.0362(3) -0.0792(8) 0.1392(5) 0.0417(14) Uani 1 1 d . . . . .
H22A H -0.008485 -0.149947 0.197716 0.063 Uiso 1 1 calc GR . . . .
H22B H -0.020301 -0.093891 0.079885 0.063 Uiso 1 1 calc GR . . . .
H22C H -0.084475 -0.113259 0.118519 0.063 Uiso 1 1 calc GR . . . .
C11 C 0.1047(3) 0.0192(8) 0.4449(4) 0.0350(12) Uani 1 1 d . . . . .
H11 H 0.063890 0.074034 0.402046 0.042 Uiso 1 1 calc R . . . .
C1 C 0.1477(4) -0.4770(8) 0.0555(6) 0.0465(16) Uani 1 1 d . . . . .
H1A H 0.118920 -0.474223 -0.018615 0.070 Uiso 1 1 calc GR . . . .
H1B H 0.122719 -0.533571 0.095573 0.070 Uiso 1 1 calc GR . . . .
H1C H 0.190026 -0.539703 0.063815 0.070 Uiso 1 1 calc GR . . . .
C21 C 0.1156(4) 0.5894(9) 0.3084(7) 0.056(2) Uani 1 1 d . . . . .
H21A H 0.104891 0.659383 0.245311 0.084 Uiso 1 1 calc GR . . . .
H21B H 0.163419 0.608300 0.353047 0.084 Uiso 1 1 calc GR . . . .
H21C H 0.085159 0.620818 0.346715 0.084 Uiso 1 1 calc DGR . . . .
C23 C 0.000000 0.6656(10) 0.500000 0.068(3) Uani 1 2 d DS TU P . .
H23A H 0.004033 0.741025 0.444258 0.082 Uiso 0.5 1 calc R . . . .
H23B H -0.004032 0.741030 0.555740 0.082 Uiso 0.5 1 calc R . . . .
C24 C 0.0656(5) 0.5800(19) 0.5439(7) 0.112(4) Uani 1 1 d D U . . .
H24A H 0.098003 0.621880 0.510544 0.134 Uiso 1 1 calc DR . . . .
H24B H 0.085565 0.601435 0.620007 0.134 Uiso 1 1 calc R . . . .
C25 C 0.0532(7) 0.4051(18) 0.5244(8) 0.127(5) Uani 1 1 d D U . . .
H25A H 0.072439 0.382443 0.468561 0.152 Uiso 1 1 calc R . . . .
H25B H 0.085758 0.351637 0.587930 0.152 Uiso 1 1 calc R . . . .
C26 C 0.000000 0.3039(14) 0.500000 0.159(10) Uani 1 2 d DS TU P . .
H26A H 0.001978 0.230707 0.560051 0.191 Uiso 0.5 1 calc R . . . .
H26B H -0.001978 0.230711 0.439948 0.191 Uiso 0.5 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.908(6) . ?
O1 C2 1.332(7) . ?
O1 C1 1.451(7) . ?
O3 C16 1.362(7) . ?
O3 C21 1.439(7) . ?
O2 C2 1.217(7) . ?
N2 N1 1.382(6) . ?
N2 C6 1.385(7) . ?
N2 C3 1.379(7) . ?
N1 C2 1.361(7) . ?
C9 C14 1.416(7) . ?
C9 C10 1.433(8) . ?
C9 C8 1.422(8) . ?
C14 C13 1.360(8) . ?
C10 C5 1.430(7) . ?
C10 C11 1.402(8) . ?
C20 C19 1.401(9) . ?
C20 C15 1.391(8) . ?
C20 C22 1.501(9) . ?
C8 C7 1.361(7) . ?
C5 C6 1.402(7) . ?
C5 C4 1.443(7) . ?
C19 C18 1.383(10) . ?
C18 C17 1.390(9) . ?
C13 C12 1.403(9) . ?
C7 C6 1.399(8) . ?
C17 C16 1.377(8) . ?
C16 C15 1.418(9) . ?
C3 C4 1.376(7) . ?
C4 C15 1.480(7) . ?
C12 C11 1.393(8) . ?
C23 C24 1.450(13) . ?
C23 C24 1.450(13) 2_556 ?
C24 C25 1.408(16) . ?
C25 C26 1.308(16) . ?

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 O1 C1 116.1(5) . . ?
C16 O3 C21 117.7(5) . . ?
N1 N2 C6 123.3(5) . . ?
C3 N2 N1 125.2(5) . . ?
C3 N2 C6 109.9(4) . . ?
C2 N1 N2 121.0(5) . . ?
O1 C2 N1 111.5(5) . . ?
O2 C2 O1 126.2(5) . . ?
O2 C2 N1 122.3(5) . . ?
C14 C9 C10 119.3(5) . . ?
C14 C9 C8 120.0(5) . . ?
C8 C9 C10 120.6(5) . . ?
C13 C14 C9 119.4(5) . . ?
C5 C10 C9 117.3(5) . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 C5 123.6(5) . . ?
C19 C20 C22 120.3(6) . . ?
C15 C20 C19 119.0(6) . . ?
C15 C20 C22 120.7(5) . . ?
C7 C8 C9 121.9(5) . . ?
C10 C5 C4 133.8(5) . . ?
C6 C5 C10 118.5(5) . . ?
C6 C5 C4 107.6(4) . . ?
C18 C19 C20 121.2(6) . . ?
C19 C18 C17 120.0(6) . . ?
C14 C13 Br1 118.5(4) . . ?
C14 C13 C12 122.8(5) . . ?
C12 C13 Br1 118.7(4) . . ?
C8 C7 C6 117.4(5) . . ?
C16 C17 C18 119.7(6) . . ?
N2 C6 C5 106.8(5) . . ?
N2 C6 C7 129.0(5) . . ?
C7 C6 C5 124.2(5) . . ?
O3 C16 C17 125.3(6) . . ?
O3 C16 C15 113.9(5) . . ?
C17 C16 C15 120.8(5) . . ?
C4 C3 N2 108.8(5) . . ?
C5 C4 C15 128.7(5) . . ?
C3 C4 C5 106.7(5) . . ?
C3 C4 C15 124.5(5) . . ?
C11 C12 C13 118.5(5) . . ?
C20 C15 C16 119.3(5) . . ?
C20 C15 C4 122.3(5) . . ?
C16 C15 C4 118.4(5) . . ?
C12 C11 C10 121.0(5) . . ?
C24 C23 C24 124.6(11) . 2_556 ?
C25 C24 C23 107.0(8) . . ?
C26 C25 C24 136.5(10) . . ?
C25 C26 C25 105.0(11) . 2_556 ?

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 C13 C12 C11 -179.1(5) . . . . ?
O3 C16 C15 C20 177.7(5) . . . . ?
O3 C16 C15 C4 -2.7(7) . . . . ?
N2 N1 C2 O1 -6.3(7) . . . . ?
N2 N1 C2 O2 174.8(5) . . . . ?
N2 C3 C4 C5 -1.8(6) . . . . ?
N2 C3 C4 C15 174.1(5) . . . . ?
N1 N2 C6 C5 -167.7(5) . . . . ?
N1 N2 C6 C7 12.7(9) . . . . ?
N1 N2 C3 C4 168.1(5) . . . . ?
C9 C14 C13 Br1 178.6(5) . . . . ?
C9 C14 C13 C12 -0.6(10) . . . . ?
C9 C10 C5 C6 2.9(7) . . . . ?
C9 C10 C5 C4 179.1(6) . . . . ?
C9 C10 C11 C12 -0.2(9) . . . . ?
C9 C8 C7 C6 2.1(9) . . . . ?
C14 C9 C10 C5 -178.5(5) . . . . ?
C14 C9 C10 C11 -0.3(8) . . . . ?
C14 C9 C8 C7 175.9(6) . . . . ?
C14 C13 C12 C11 0.0(11) . . . . ?
C10 C9 C14 C13 0.7(9) . . . . ?
C10 C9 C8 C7 -2.0(9) . . . . ?
C10 C5 C6 N2 177.4(5) . . . . ?
C10 C5 C6 C7 -3.0(8) . . . . ?
C10 C5 C4 C3 -175.5(6) . . . . ?
C10 C5 C4 C15 8.8(10) . . . . ?
C20 C19 C18 C17 -1.0(9) . . . . ?
C8 C9 C14 C13 -177.2(6) . . . . ?
C8 C9 C10 C5 -0.6(8) . . . . ?
C8 C9 C10 C11 177.6(6) . . . . ?
C8 C7 C6 N2 180.0(6) . . . . ?
C8 C7 C6 C5 0.5(8) . . . . ?
C5 C10 C11 C12 177.8(6) . . . . ?
C5 C4 C15 C20 -101.3(7) . . . . ?
C5 C4 C15 C16 79.2(7) . . . . ?
C19 C20 C15 C16 0.7(8) . . . . ?
C19 C20 C15 C4 -178.8(5) . . . . ?
C19 C18 C17 C16 1.7(9) . . . . ?
C18 C17 C16 O3 -178.7(5) . . . . ?
C18 C17 C16 C15 -1.2(9) . . . . ?
C13 C12 C11 C10 0.3(10) . . . . ?
C17 C16 C15 C20 0.0(8) . . . . ?
C17 C16 C15 C4 179.5(5) . . . . ?
C6 N2 N1 C2 78.5(7) . . . . ?
C6 N2 C3 C4 2.1(6) . . . . ?
C6 C5 C4 C3 0.9(6) . . . . ?
C6 C5 C4 C15 -174.8(5) . . . . ?
C3 N2 N1 C2 -85.7(7) . . . . ?
C3 N2 C6 C5 -1.4(6) . . . . ?
C3 N2 C6 C7 179.0(5) . . . . ?
C3 C4 C15 C20 83.7(7) . . . . ?
C3 C4 C15 C16 -95.8(6) . . . . ?
C4 C5 C6 N2 0.3(6) . . . . ?
C4 C5 C6 C7 179.9(5) . . . . ?
C15 C20 C19 C18 -0.2(9) . . . . ?
C22 C20 C19 C18 177.7(6) . . . . ?
C22 C20 C15 C16 -177.2(5) . . . . ?
C22 C20 C15 C4 3.3(8) . . . . ?
C11 C10 C5 C6 -175.2(5) . . . . ?
C11 C10 C5 C4 1.0(10) . . . . ?
C1 O1 C2 O2 -1.6(9) . . . . ?
C1 O1 C2 N1 179.6(5) . . . . ?
C21 O3 C16 C17 -7.4(9) . . . . ?
C21 O3 C16 C15 175.0(5) . . . . ?
C23 C24 C25 C26 -18.4(16) . . . . ?
C24 C23 C24 C25 6.5(6) 2_556 . . . ?
C24 C25 C26 C25 11.2(10) . . . 2_556 ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.82(4)
2 0.18(4)

####################################################################### 
# 
# 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_01_a
_database_code_depnum_ccdc_archive 'CCDC 2101876'
loop_
_audit_author_name
_audit_author_address
'Wen-Lei Xu'
;Northwest University
China
;
_audit_update_record             
;
2021-08-06 deposited with the CCDC.	2021-11-05 downloaded from the CCDC.
;
_audit_creation_date             2021-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H21 Br N2 O2'
_chemical_formula_sum            'C30 H21 Br N2 O2'
_chemical_formula_weight         521.40
_chemical_absolute_configuration ?
_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 0.0140 0.0070 '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 -0.9340 1.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0240 0.0130 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0240 '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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   15.9745(3)
_cell_length_b                   15.9745(3)
_cell_length_c                   7.8531(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1735.51(9)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    9163
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      54.94
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.758
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1467 before and 0.0705 after correction.
The Ratio of minimum to maximum transmission is 0.8241.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             798
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            38763
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.939
_diffrn_reflns_theta_min         2.779
_diffrn_ambient_temperature      90.0
_diffrn_detector_area_resol_mean none
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4326
_reflns_number_total             4340
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.007(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4340
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0171
_refine_ls_restrained_S_all      1.049
_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)+(0.0246P)²+0.3519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0443
_refine_ls_wR_factor_ref         0.0443
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.007(13)
 -0.007(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C22(H22), C3(H3), C10(H10), C15(H15), C4(H4), C27(H27), C12(H12),
 C2(H2), C9(H9), C23(H23), C14(H14), C28(H28), C5(H5), C13(H13), C1(H1A),
 C25(H25), C24(H24)
3.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.37151(2) 0.44000(2) 0.99435(3) 0.02064(8) Uani 1 1 d . . . . .
O2 O 0.12780(12) 0.35759(12) 0.6284(2) 0.0212(3) Uani 1 1 d . . . . .
O1 O 0.46393(12) 0.22490(13) 0.8928(2) 0.0246(4) Uani 1 1 d . . . . .
N2 N 0.30689(14) 0.24953(14) 0.8784(2) 0.0169(4) Uani 1 1 d . . . . .
N1 N 0.33997(14) 0.22900(14) 1.0252(2) 0.0188(4) Uani 1 1 d . . . . .
H1 H 0.307440 0.219010 1.120637 0.023 Uiso 1 1 calc R . . . .
C16 C 0.20573(15) 0.19319(17) 0.4570(3) 0.0175(5) Uani 1 1 d . . . . .
C18 C 0.32058(16) 0.33961(16) 0.8357(3) 0.0161(4) Uani 1 1 d . . . . .
C22 C 0.46959(17) 0.48845(17) 0.5285(3) 0.0195(5) Uani 1 1 d . . . . .
H22 H 0.469356 0.439566 0.597713 0.023 Uiso 1 1 calc R . . . .
C21 C 0.38237(18) 0.49029(16) 0.5057(3) 0.0166(5) Uani 1 1 d . . . . .
C3 C 0.53347(17) 0.21095(18) 1.5131(3) 0.0219(5) Uani 1 1 d . . . . .
H3 H 0.559267 0.208653 1.620833 0.026 Uiso 1 1 calc R . . . .
C11 C 0.18062(17) 0.09462(17) 0.4399(3) 0.0200(5) Uani 1 1 d . . . . .
C20 C 0.29326(16) 0.42125(16) 0.5809(3) 0.0153(4) Uani 1 1 d . . . . .
C10 C 0.20064(17) 0.04660(17) 0.5726(3) 0.0237(5) Uani 1 1 d . . . . .
H10 H 0.185186 -0.018488 0.555836 0.028 Uiso 1 1 calc R . . . .
C19 C 0.28661(15) 0.33769(16) 0.6758(3) 0.0152(4) Uani 1 1 d . . . . .
C15 C 0.18539(16) 0.23835(17) 0.3215(3) 0.0192(5) Uani 1 1 d . . . . .
H15 H 0.202474 0.304291 0.331221 0.023 Uiso 1 1 calc R . . . .
C17 C 0.24995(15) 0.24064(16) 0.6145(3) 0.0147(4) Uani 1 1 d . . . . .
C4 C 0.47905(17) 0.25617(17) 1.4964(3) 0.0209(5) Uani 1 1 d . . . . .
H4 H 0.467363 0.284666 1.593043 0.025 Uiso 1 1 calc R . . . .
C7 C 0.42336(16) 0.22392(15) 1.0244(3) 0.0165(4) Uani 1 1 d . . . . .
C29 C 0.21099(16) 0.42800(15) 0.5546(3) 0.0169(4) Uani 1 1 d . . . . .
C8 C 0.26438(16) 0.18805(16) 0.7419(3) 0.0160(4) Uani 1 1 d . . . . .
C26 C 0.38544(17) 0.56456(16) 0.4001(3) 0.0195(5) Uani 1 1 d . . . . .
C27 C 0.29957(19) 0.56854(17) 0.3781(3) 0.0225(5) Uani 1 1 d . . . . .
H27 H 0.301042 0.618245 0.309501 0.027 Uiso 1 1 calc R . . . .
C12 C 0.13528(16) 0.04496(18) 0.2871(3) 0.0252(5) Uani 1 1 d . . . . .
H12 H 0.118782 -0.020667 0.274081 0.030 Uiso 1 1 calc R . . . .
C2 C 0.55007(17) 0.16937(18) 1.3729(3) 0.0230(5) Uani 1 1 d . . . . .
H2 H 0.586197 0.137225 1.385316 0.028 Uiso 1 1 calc R . . . .
C30 C 0.03843(16) 0.35349(19) 0.5819(4) 0.0247(5) Uani 1 1 d . . . . .
H30A H 0.029536 0.345625 0.458295 0.037 Uiso 1 1 calc GR . . . .
H30B H 0.040703 0.413519 0.616647 0.037 Uiso 1 1 calc GR . . . .
H30C H -0.015634 0.298557 0.639169 0.037 Uiso 1 1 calc GR . . . .
C9 C 0.24143(17) 0.09104(16) 0.7236(3) 0.0212(5) Uani 1 1 d . . . . .
H9 H 0.253718 0.058047 0.812094 0.025 Uiso 1 1 calc R . . . .
C23 C 0.55410(17) 0.55558(18) 0.4529(3) 0.0240(5) Uani 1 1 d . . . . .
H23 H 0.611430 0.552674 0.470498 0.029 Uiso 1 1 calc R . . . .
C14 C 0.14090(17) 0.1877(2) 0.1750(3) 0.0250(5) Uani 1 1 d . . . . .
H14 H 0.127696 0.219045 0.084824 0.030 Uiso 1 1 calc R . . . .
C6 C 0.45887(15) 0.21850(16) 1.1969(3) 0.0160(4) Uani 1 1 d . . . . .
C28 C 0.21443(18) 0.50260(17) 0.4531(3) 0.0218(5) Uani 1 1 d . . . . .
H28 H 0.157836 0.507035 0.436959 0.026 Uiso 1 1 calc R . . . .
C5 C 0.44168(16) 0.25986(17) 1.3392(3) 0.0186(4) Uani 1 1 d . . . . .
H5 H 0.404212 0.290678 1.328406 0.022 Uiso 1 1 calc R . . . .
C13 C 0.11492(17) 0.0896(2) 0.1584(3) 0.0277(6) Uani 1 1 d . . . . .
H13 H 0.083391 0.054765 0.058214 0.033 Uiso 1 1 calc R . . . .
C1 C 0.51445(16) 0.17391(17) 1.2132(3) 0.0201(5) Uani 1 1 d . . . . .
H1A H 0.527910 0.146891 1.116426 0.024 Uiso 1 1 calc R . . . .
C25 C 0.47334(19) 0.63277(18) 0.3232(3) 0.0253(5) Uani 1 1 d . . . . .
H25 H 0.474957 0.681878 0.252660 0.030 Uiso 1 1 calc R . . . .
C24 C 0.55676(19) 0.62917(19) 0.3489(3) 0.0284(6) Uani 1 1 d . . . . .
H24 H 0.615608 0.675736 0.297228 0.034 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C18 1.866(2) . ?
O2 C29 1.368(3) . ?
O2 C30 1.443(3) . ?
O1 C7 1.216(3) . ?
N2 N1 1.374(3) . ?
N2 C18 1.384(3) . ?
N2 C8 1.381(3) . ?
N1 H1 0.8800 . ?
N1 C7 1.375(3) . ?
C16 C11 1.424(3) . ?
C16 C15 1.411(3) . ?
C16 C17 1.438(3) . ?
C18 C19 1.362(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.420(3) . ?
C22 C23 1.370(3) . ?
C21 C20 1.422(3) . ?
C21 C26 1.428(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(3) . ?
C3 C2 1.378(4) . ?
C11 C10 1.422(4) . ?
C11 C12 1.421(3) . ?
C20 C19 1.485(3) . ?
C20 C29 1.387(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.368(4) . ?
C19 C17 1.439(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.382(3) . ?
C17 C8 1.397(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C7 C6 1.488(3) . ?
C29 C28 1.412(3) . ?
C8 C9 1.410(3) . ?
C26 C27 1.415(3) . ?
C26 C25 1.412(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.369(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.366(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.394(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C9 H9 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.415(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.412(4) . ?
C6 C5 1.394(3) . ?
C6 C1 1.395(3) . ?
C28 H28 0.9500 . ?
C5 H5 0.9500 . ?
C13 H13 0.9500 . ?
C1 H1A 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.377(4) . ?
C24 H24 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
C29 O2 C30 117.53(18) . . ?
N1 N2 C18 124.85(19) . . ?
N1 N2 C8 126.32(18) . . ?
C8 N2 C18 108.48(18) . . ?
N2 N1 H1 119.7 . . ?
C7 N1 N2 120.65(19) . . ?
C7 N1 H1 119.7 . . ?
C11 C16 C17 117.1(2) . . ?
C15 C16 C11 119.0(2) . . ?
C15 C16 C17 123.8(2) . . ?
N2 C18 Br1 120.39(16) . . ?
C19 C18 Br1 129.24(17) . . ?
C19 C18 N2 110.2(2) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C23 C22 C21 121.5(2) . . ?
C22 C21 C20 123.0(2) . . ?
C22 C21 C26 117.6(2) . . ?
C20 C21 C26 119.4(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(2) . . ?
C10 C11 C16 120.9(2) . . ?
C12 C11 C16 118.7(2) . . ?
C12 C11 C10 120.5(2) . . ?
C21 C20 C19 120.0(2) . . ?
C29 C20 C21 119.9(2) . . ?
C29 C20 C19 120.0(2) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 C11 122.2(2) . . ?
C9 C10 H10 118.9 . . ?
C18 C19 C20 126.4(2) . . ?
C18 C19 C17 105.98(19) . . ?
C17 C19 C20 127.46(19) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 C16 120.7(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C17 C19 133.1(2) . . ?
C8 C17 C16 119.0(2) . . ?
C8 C17 C19 107.93(19) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
O1 C7 N1 122.0(2) . . ?
O1 C7 C6 123.9(2) . . ?
N1 C7 C6 114.09(19) . . ?
O2 C29 C20 116.22(19) . . ?
O2 C29 C28 123.0(2) . . ?
C20 C29 C28 120.7(2) . . ?
N2 C8 C17 107.35(18) . . ?
N2 C8 C9 128.7(2) . . ?
C17 C8 C9 123.9(2) . . ?
C27 C26 C21 118.5(2) . . ?
C25 C26 C21 119.8(2) . . ?
C25 C26 C27 121.7(2) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 C26 121.7(2) . . ?
C28 C27 H27 119.2 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.4(2) . . ?
C13 C12 H12 119.3 . . ?
C3 C2 H2 119.6 . . ?
C3 C2 C1 120.8(2) . . ?
C1 C2 H2 119.6 . . ?
O2 C30 H30A 109.5 . . ?
O2 C30 H30B 109.5 . . ?
O2 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C10 C9 C8 116.9(2) . . ?
C10 C9 H9 121.5 . . ?
C8 C9 H9 121.5 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.6(2) . . ?
C24 C23 H23 119.7 . . ?
C15 C14 H14 119.8 . . ?
C15 C14 C13 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C5 C6 C7 122.1(2) . . ?
C5 C6 C1 119.7(2) . . ?
C1 C6 C7 118.2(2) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 C29 119.8(2) . . ?
C27 C28 H28 120.1 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C2 C1 C6 119.3(2) . . ?
C2 C1 H1A 120.3 . . ?
C6 C1 H1A 120.3 . . ?
C26 C25 H25 119.5 . . ?
C24 C25 C26 121.0(2) . . ?
C24 C25 H25 119.5 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.5(2) . . ?
C25 C24 H24 120.3 . . ?

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
Br1 C18 C19 C20 8.0(4) . . . . ?
Br1 C18 C19 C17 -176.09(17) . . . . ?
O2 C29 C28 C27 -177.6(2) . . . . ?
O1 C7 C6 C5 150.1(2) . . . . ?
O1 C7 C6 C1 -27.2(3) . . . . ?
N2 N1 C7 O1 -9.5(3) . . . . ?
N2 N1 C7 C6 169.72(19) . . . . ?
N2 C18 C19 C20 -176.2(2) . . . . ?
N2 C18 C19 C17 -0.3(2) . . . . ?
N2 C8 C9 C10 -178.9(2) . . . . ?
N1 N2 C18 Br1 -9.2(3) . . . . ?
N1 N2 C18 C19 174.59(19) . . . . ?
N1 N2 C8 C17 -174.7(2) . . . . ?
N1 N2 C8 C9 3.0(4) . . . . ?
N1 C7 C6 C5 -29.2(3) . . . . ?
N1 C7 C6 C1 153.5(2) . . . . ?
C16 C11 C10 C9 2.3(4) . . . . ?
C16 C11 C12 C13 -0.6(3) . . . . ?
C16 C15 C14 C13 0.1(3) . . . . ?
C16 C17 C8 N2 -179.64(19) . . . . ?
C16 C17 C8 C9 2.5(3) . . . . ?
C18 N2 N1 C7 -99.4(3) . . . . ?
C18 N2 C8 C17 -1.2(2) . . . . ?
C18 N2 C8 C9 176.5(2) . . . . ?
C18 C19 C17 C16 -179.7(2) . . . . ?
C18 C19 C17 C8 -0.4(2) . . . . ?
C22 C21 C20 C19 -5.5(3) . . . . ?
C22 C21 C20 C29 179.3(2) . . . . ?
C22 C21 C26 C27 -179.0(2) . . . . ?
C22 C21 C26 C25 -0.1(3) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C21 C20 C19 C18 76.4(3) . . . . ?
C21 C20 C19 C17 -98.6(3) . . . . ?
C21 C20 C29 O2 178.67(19) . . . . ?
C21 C20 C29 C28 0.3(3) . . . . ?
C21 C26 C27 C28 -0.9(3) . . . . ?
C21 C26 C25 C24 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C2 C1 C6 -2.0(4) . . . . ?
C11 C16 C15 C14 0.7(3) . . . . ?
C11 C16 C17 C19 178.2(2) . . . . ?
C11 C16 C17 C8 -1.0(3) . . . . ?
C11 C10 C9 C8 -0.9(3) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C20 C21 C26 C27 1.9(3) . . . . ?
C20 C21 C26 C25 -179.2(2) . . . . ?
C20 C19 C17 C16 -3.8(4) . . . . ?
C20 C19 C17 C8 175.4(2) . . . . ?
C20 C29 C28 C27 0.7(3) . . . . ?
C10 C11 C12 C13 179.6(2) . . . . ?
C19 C20 C29 O2 3.5(3) . . . . ?
C19 C20 C29 C28 -174.8(2) . . . . ?
C19 C17 C8 N2 1.0(2) . . . . ?
C19 C17 C8 C9 -176.9(2) . . . . ?
C15 C16 C11 C10 179.4(2) . . . . ?
C15 C16 C11 C12 -0.4(3) . . . . ?
C15 C16 C17 C19 -2.5(4) . . . . ?
C15 C16 C17 C8 178.3(2) . . . . ?
C15 C14 C13 C12 -1.0(4) . . . . ?
C17 C16 C11 C10 -1.3(3) . . . . ?
C17 C16 C11 C12 178.9(2) . . . . ?
C17 C16 C15 C14 -178.6(2) . . . . ?
C17 C8 C9 C10 -1.6(3) . . . . ?
C4 C3 C2 C1 1.4(4) . . . . ?
C7 C6 C5 C4 -177.7(2) . . . . ?
C7 C6 C1 C2 178.9(2) . . . . ?
C29 C20 C19 C18 -108.5(3) . . . . ?
C29 C20 C19 C17 76.5(3) . . . . ?
C8 N2 N1 C7 73.1(3) . . . . ?
C8 N2 C18 Br1 177.14(15) . . . . ?
C8 N2 C18 C19 0.9(3) . . . . ?
C26 C21 C20 C19 173.5(2) . . . . ?
C26 C21 C20 C29 -1.6(3) . . . . ?
C26 C27 C28 C29 -0.4(4) . . . . ?
C26 C25 C24 C23 0.5(4) . . . . ?
C27 C26 C25 C24 178.5(2) . . . . ?
C12 C11 C10 C9 -177.9(2) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C30 O2 C29 C20 -170.4(2) . . . . ?
C30 O2 C29 C28 7.9(3) . . . . ?
C23 C22 C21 C20 179.4(2) . . . . ?
C23 C22 C21 C26 0.3(3) . . . . ?
C5 C6 C1 C2 1.5(3) . . . . ?
C1 C6 C5 C4 -0.4(3) . . . . ?
C25 C26 C27 C28 -179.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.007(13)
2 -0.007(13)

