# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# 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_4BrAzo_trans_alpha
_database_code_depnum_ccdc_archive 'CCDC 2295252'
loop_
_audit_author_name
_audit_author_address
'Yasuo Norikane'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2023-09-15 deposited with the CCDC.	2023-12-11 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         ?
_chemical_formula_sum            'C12 H6 Br4 N2'
_chemical_formula_weight         497.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.64(4)
_cell_length_b                   12.14(3)
_cell_length_c                   8.31(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.61(3)
_cell_angle_gamma                90
_cell_volume                     1457(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    1475
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.270
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    11.035
_shelx_estimated_absorpt_T_min   0.073
_shelx_estimated_absorpt_T_max   0.405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.190
_exptl_absorpt_correction_T_max  0.331
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6993
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.356
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1658
_reflns_number_gt                1141
_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    ?
_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)+(0.1000P)²] 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         1658
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1846
_refine_ls_wR_factor_gt          0.1711
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.42858(6) 0.62265(8) 0.49496(12) 0.0556(4) Uani 1 1 d . . . . .
Br2 Br 0.37559(7) 0.98874(7) 0.03997(12) 0.0526(4) Uani 1 1 d . . . . .
N4 N 0.4873(4) 0.7993(4) 0.3122(7) 0.0320(12) Uani 1 1 d . . . . .
C5 C 0.3294(5) 0.8770(6) 0.1429(9) 0.0379(17) Uani 1 1 d . . . . .
C6 C 0.3885(5) 0.8012(5) 0.2592(9) 0.0304(14) Uani 1 1 d . . . . .
C7 C 0.2562(5) 0.7244(7) 0.3006(11) 0.0442(19) Uani 1 1 d . . . . .
H7 H 0.231109 0.672359 0.355792 0.053 Uiso 1 1 calc R U . . .
C8 C 0.3510(5) 0.7270(6) 0.3372(9) 0.0364(16) Uani 1 1 d . . . . .
C9 C 0.2006(6) 0.7983(8) 0.1842(11) 0.049(2) Uani 1 1 d . . . . .
H9 H 0.135654 0.796395 0.155723 0.058 Uiso 1 1 calc R U . . .
C10 C 0.2364(6) 0.8750(7) 0.1074(11) 0.050(2) Uani 1 1 d . . . . .
H10 H 0.196662 0.927293 0.028984 0.061 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 1.890(8) . ?
Br2 C5 1.888(9) . ?
N4 N4 1.241(12) 2_655 ?
N4 C6 1.436(10) . ?
C5 C10 1.369(13) . ?
C5 C6 1.396(10) . ?
C6 C8 1.367(10) . ?
C7 C9 1.360(13) . ?
C7 C8 1.394(11) . ?
C9 C10 1.366(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 N4 C6 113.3(7) 2_655 . ?
C10 C5 C6 120.2(8) . . ?
C10 C5 Br2 118.3(6) . . ?
C6 C5 Br2 121.4(6) . . ?
C8 C6 C5 118.2(7) . . ?
C8 C6 N4 116.9(6) . . ?
C5 C6 N4 124.8(7) . . ?
C9 C7 C8 118.5(8) . . ?
C6 C8 C7 121.7(7) . . ?
C6 C8 Br1 119.5(6) . . ?
C7 C8 Br1 118.8(6) . . ?
C7 C9 C10 121.1(8) . . ?
C5 C10 C9 120.3(8) . . ?

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
C10 C5 C6 C8 -0.9(11) . . . . ?
Br2 C5 C6 C8 175.9(5) . . . . ?
C10 C5 C6 N4 -176.8(7) . . . . ?
Br2 C5 C6 N4 0.0(10) . . . . ?
N4 N4 C6 C8 132.1(5) 2_655 . . . ?
N4 N4 C6 C5 -52.0(7) 2_655 . . . ?
C5 C6 C8 C7 1.2(11) . . . . ?
N4 C6 C8 C7 177.4(7) . . . . ?
C5 C6 C8 Br1 179.8(5) . . . . ?
N4 C6 C8 Br1 -4.0(9) . . . . ?
C9 C7 C8 C6 0.0(12) . . . . ?
C9 C7 C8 Br1 -178.6(6) . . . . ?
C8 C7 C9 C10 -1.5(12) . . . . ?
C6 C5 C10 C9 -0.6(12) . . . . ?
Br2 C5 C10 C9 -177.5(6) . . . . ?
C7 C9 C10 C5 1.9(13) . . . . ?

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
C7 H7 Br2 0.95 3.10 4.036(11) 168.5 4_545 yes
C10 H10 Br1 0.95 3.03 3.839(11) 143.5 4 yes

_refine_diff_density_max         1.201
_refine_diff_density_min         -1.239
_refine_diff_density_rms         0.215

####################################################################### 
# 
# 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_4BrAzo_cis
_database_code_depnum_ccdc_archive 'CCDC 2295253'
loop_
_audit_author_name
_audit_author_address
'Yasuo Norikane'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2023-09-15 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT341_4BrAzo_cis          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02667 Ang.
RESPONSE: Due to the thermal instability of the cis isomer it is not possible to grow completely ideal crystals. This may explain the lower C-C bond precision. However, given the similarities in the simulated powder XRD pattern generated from this structure with the measured diffraction pattern we believe the currently solved structure is reasonable.
;
# Added during the CSD deposition process: Friday 15 September 2023 12:21 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 Br4 N2'
_chemical_formula_weight         497.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   11.13(2)
_cell_length_b                   7.520(13)
_cell_length_c                   16.82(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.223(19)
_cell_angle_gamma                90
_cell_volume                     1329(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2192
_cell_measurement_theta_min      3.30
_cell_measurement_theta_max      27.50

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.488
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    12.091
_shelx_estimated_absorpt_T_min   0.196
_shelx_estimated_absorpt_T_max   0.378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.222
_exptl_absorpt_correction_T_max  0.297
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13295
_diffrn_reflns_av_unetI/netI     0.1142
_diffrn_reflns_av_R_equivalents  0.1363
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.331
_diffrn_reflns_theta_max         27.805
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3124
_reflns_number_gt                1837
_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    ?
_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)+(0.0898P)²+21.0366P] 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         3124
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1802
_refine_ls_R_factor_gt           0.1144
_refine_ls_wR_factor_ref         0.2757
_refine_ls_wR_factor_gt          0.2395
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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 0.44262(19) 0.3103(3) 0.42281(13) 0.0603(6) Uani 1 1 d . . . . .
Br2 Br 0.78966(19) 0.2398(3) 0.54427(11) 0.0579(6) Uani 1 1 d . . . . .
Br3 Br 0.9090(2) 0.5326(3) 0.27054(12) 0.0602(6) Uani 1 1 d . . . . .
Br4 Br 0.78117(19) 0.0847(3) 0.25571(13) 0.0616(6) Uani 1 1 d . . . . .
N9 N 0.6374(15) 0.3601(18) 0.3449(9) 0.047(4) Uani 1 1 d . . . . .
N12 N 0.7406(15) 0.439(2) 0.3682(10) 0.052(4) Uani 1 1 d . . . . .
C5 C 0.6713(13) 0.041(2) 0.3141(10) 0.042(4) Uani 1 1 d . . . . .
C6 C 0.6214(14) 0.176(2) 0.3504(9) 0.036(3) Uani 1 1 d . . . . .
C7 C 0.4885(17) -0.038(2) 0.3850(11) 0.048(4) Uani 1 1 d . . . . .
H7 H 0.422438 -0.065349 0.407235 0.057 Uiso 1 1 calc R U . . .
C8 C 0.8607(18) 0.359(2) 0.4051(10) 0.043(4) Uani 1 1 d . . . . .
C10 C 0.5513(19) -0.177(3) 0.3558(11) 0.060(6) Uani 1 1 d . . . . .
H10 H 0.531394 -0.298354 0.362153 0.072 Uiso 1 1 calc R U . . .
C11 C 1.0252(19) 0.210(2) 0.5179(13) 0.055(5) Uani 1 1 d . . . . .
H11 H 1.049399 0.144894 0.569119 0.066 Uiso 1 1 calc R U . . .
C14 C 0.5241(16) 0.129(2) 0.3804(9) 0.047(4) Uani 1 1 d . . . . .
C15 C 0.6341(16) -0.138(3) 0.3211(10) 0.049(4) Uani 1 1 d . . . . .
H15 H 0.672080 -0.231397 0.299427 0.058 Uiso 1 1 calc R U . . .
C18 C 0.9031(18) 0.267(2) 0.4823(11) 0.048(4) Uani 1 1 d . . . . .
C20 C 1.0776(18) 0.333(3) 0.4033(11) 0.051(5) Uani 1 1 d . . . . .
H20 H 1.136346 0.344277 0.373501 0.061 Uiso 1 1 calc R U . . .
C21 C 0.9537(19) 0.403(2) 0.3697(11) 0.050(5) Uani 1 1 d . . . . .
C22 C 1.1121(18) 0.248(2) 0.4796(12) 0.055(5) Uani 1 1 d . . . . .
H22 H 1.198423 0.214890 0.506227 0.066 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 C14 1.900(19) . ?
Br2 C18 1.894(18) . ?
Br3 C21 1.855(18) . ?
Br4 C5 1.833(16) . ?
N9 N12 1.237(19) . ?
N9 C6 1.40(2) . ?
N12 C8 1.41(2) . ?
C5 C6 1.39(2) . ?
C5 C15 1.43(2) . ?
C6 C14 1.38(2) . ?
C7 C14 1.33(2) . ?
C7 C10 1.43(3) . ?
C8 C21 1.39(2) . ?
C8 C18 1.41(2) . ?
C10 C15 1.28(2) . ?
C11 C22 1.36(2) . ?
C11 C18 1.36(3) . ?
C20 C22 1.37(3) . ?
C20 C21 1.41(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N9 C6 125.4(16) . . ?
N9 N12 C8 125.4(15) . . ?
C6 C5 C15 119.0(14) . . ?
C6 C5 Br4 122.4(12) . . ?
C15 C5 Br4 118.6(14) . . ?
C14 C6 C5 116.6(15) . . ?
C14 C6 N9 114.0(15) . . ?
C5 C6 N9 127.9(14) . . ?
C14 C7 C10 118.9(17) . . ?
C21 C8 C18 116.1(18) . . ?
C21 C8 N12 116.2(15) . . ?
C18 C8 N12 126.7(16) . . ?
C15 C10 C7 119.7(18) . . ?
C22 C11 C18 119.3(18) . . ?
C7 C14 C6 123.1(18) . . ?
C7 C14 Br1 118.0(14) . . ?
C6 C14 Br1 118.9(14) . . ?
C10 C15 C5 121.9(18) . . ?
C11 C18 C8 122.9(17) . . ?
C11 C18 Br2 118.3(14) . . ?
C8 C18 Br2 118.6(15) . . ?
C22 C20 C21 119.0(16) . . ?
C8 C21 C20 120.6(17) . . ?
C8 C21 Br3 119.4(15) . . ?
C20 C21 Br3 119.7(12) . . ?
C11 C22 C20 121.2(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 N9 N12 C8 -1(3) . . . . ?
C15 C5 C6 C14 -9(2) . . . . ?
Br4 C5 C6 C14 169.6(11) . . . . ?
C15 C5 C6 N9 -174.4(15) . . . . ?
Br4 C5 C6 N9 4(2) . . . . ?
N12 N9 C6 C14 135.2(16) . . . . ?
N12 N9 C6 C5 -59(2) . . . . ?
N9 N12 C8 C21 129.5(17) . . . . ?
N9 N12 C8 C18 -63(2) . . . . ?
C14 C7 C10 C15 -4(3) . . . . ?
C10 C7 C14 C6 -2(3) . . . . ?
C10 C7 C14 Br1 -178.1(12) . . . . ?
C5 C6 C14 C7 8(2) . . . . ?
N9 C6 C14 C7 175.4(16) . . . . ?
C5 C6 C14 Br1 -175.2(11) . . . . ?
N9 C6 C14 Br1 -8.0(19) . . . . ?
C7 C10 C15 C5 3(3) . . . . ?
C6 C5 C15 C10 4(2) . . . . ?
Br4 C5 C15 C10 -175.0(14) . . . . ?
C22 C11 C18 C8 2(3) . . . . ?
C22 C11 C18 Br2 -171.9(13) . . . . ?
C21 C8 C18 C11 -5(2) . . . . ?
N12 C8 C18 C11 -172.6(16) . . . . ?
C21 C8 C18 Br2 169.1(11) . . . . ?
N12 C8 C18 Br2 1(2) . . . . ?
C18 C8 C21 C20 10(2) . . . . ?
N12 C8 C21 C20 178.5(15) . . . . ?
C18 C8 C21 Br3 -177.3(11) . . . . ?
N12 C8 C21 Br3 -8.4(19) . . . . ?
C22 C20 C21 C8 -12(2) . . . . ?
C22 C20 C21 Br3 175.4(12) . . . . ?
C18 C11 C22 C20 -4(3) . . . . ?
C21 C20 C22 C11 9(3) . . . . ?

_refine_diff_density_max         1.685
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.230

####################################################################### 
# 
# 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_4BrAzo_trans_beta
_database_code_depnum_ccdc_archive 'CCDC 2295254'
loop_
_audit_author_name
_audit_author_address
'Yasuo Norikane'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2023-09-15 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_audit_creation_date             2023-04-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C12 H6 Br4 N2)'
_chemical_formula_sum            'C12 H6 Br4 N2'
_chemical_formula_weight         497.83
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   23.3728(11)
_cell_length_b                   8.6091(4)
_cell_length_c                   14.1715(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.079(5)
_cell_angle_gamma                90
_cell_volume                     2788.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12013
_cell_measurement_temperature    170.15
_cell_measurement_theta_max      32.5880
_cell_measurement_theta_min      2.6640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    11.528
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.50a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35288
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.418
_diffrn_reflns_theta_min         2.528
_diffrn_ambient_temperature      170.15
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 120.00   1.00   16.00    --   30.00  54.00   0.00  180
  2  ω    -60.00 120.00   1.00   16.00    --   30.00  54.00 120.00  180
  3  ω    -60.00 120.00   1.00   16.00    --   30.00  54.00 240.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0278704000
_diffrn_orient_matrix_UB_12      0.0237082000
_diffrn_orient_matrix_UB_13      -0.0069772000
_diffrn_orient_matrix_UB_21      0.0077258000
_diffrn_orient_matrix_UB_22      0.0236881000
_diffrn_orient_matrix_UB_23      0.0489601000
_diffrn_orient_matrix_UB_31      0.0112179000
_diffrn_orient_matrix_UB_32      -0.0752875000
_diffrn_orient_matrix_UB_33      0.0132205000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6579
_reflns_number_total             9693
_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       'CrysAlisPro 1.171.43.50a (Rigaku OD, 2022)'
_computing_data_collection       
'DTREK_VERSION=d*TREK version 9.9.9.4 W9RSSI -- Mar 27 2012'
_computing_data_reduction        'CrysAlisPro 1.171.43.50a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.901
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     416
_refine_ls_number_reflns         9693
_refine_ls_number_restraints     222
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.005
_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)+(0.0431P)²+0.9475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0947
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Br7 \\sim Br8 \\sim C21 \\sim C19 \\sim C20 \\sim C23 \\sim C22 \\sim C24 \\sim
N4: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
N4A \\sim Br8A \\sim C24A \\sim C19A \\sim C20A \\sim C21A \\sim C22A \\sim
C23A \\sim Br7A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
3. Rigid body (RIGU) restrains
 Br7, Br8, C21, C19, C20, C23, C22, C24, N4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N4A, Br8A, C24A, C19A, C20A, C21A, C22A, C23A, Br7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(N4A)=Sof(N3A)=Sof(Br8A)=Sof(C24A)=Sof(C19A)=Sof(C20A)=Sof(C21A)=Sof(H21A)=
 Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(Br7A)=1-FVAR(1)
 Sof(Br7)=Sof(Br8)=Sof(N3)=Sof(C21)=Sof(H21)=Sof(C19)=Sof(C20)=Sof(C23)=
 Sof(H23)=Sof(C22)=Sof(H22)=Sof(C24)=Sof(N4)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C4(H4), C11(H11), C9(H9), C21(H21), C17(H17), C10(H10),
 C15(H15), C16(H16), C23(H23), C22(H22), C21A(H21A), C22A(H22A), C23A(H23A)
;
_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 0.42906(2) 0.43312(4) 0.70694(2) 0.02859(8) Uani 1 1 d . . . . .
Br2 Br 0.46985(2) 0.85006(4) 0.41456(2) 0.02677(8) Uani 1 1 d . . . . .
Br3 Br 0.34963(2) 1.08104(4) 0.60262(3) 0.03238(9) Uani 1 1 d . . . . .
Br4 Br 0.28656(2) 0.45104(4) 0.50941(3) 0.03630(10) Uani 1 1 d . . . . .
Br5 Br 0.12375(2) 0.29626(5) 0.44491(3) 0.04091(10) Uani 1 1 d . . . . .
Br6 Br 0.02143(2) 0.54369(5) 0.74964(3) 0.04241(11) Uani 1 1 d . . . . .
Br7 Br 0.13942(13) 0.9238(6) 0.69592(19) 0.0372(5) Uani 0.555(14) 1 d . U P A 1
Br8 Br 0.2282(3) 0.3022(4) 0.7593(3) 0.0505(6) Uani 0.555(14) 1 d . U P A 1
N1 N 0.39683(12) 0.6783(3) 0.53100(18) 0.0220(5) Uani 1 1 d . . . . .
N2 N 0.37121(12) 0.7392(3) 0.58991(19) 0.0221(6) Uani 1 1 d . . . . .
C1 C 0.45782(14) 0.6517(3) 0.5703(2) 0.0194(6) Uani 1 1 d . . . . .
C3 C 0.53936(15) 0.5301(4) 0.6796(2) 0.0249(7) Uani 1 1 d . . . . .
H3 H 0.553433 0.462529 0.732328 0.030 Uiso 1 1 calc R U . . .
C7 C 0.31045(14) 0.7741(4) 0.5480(2) 0.0207(6) Uani 1 1 d . . . . .
C2 C 0.48000(14) 0.5525(3) 0.6475(2) 0.0205(6) Uani 1 1 d . . . . .
C6 C 0.49802(14) 0.7230(3) 0.5238(2) 0.0206(6) Uani 1 1 d . . . . .
C5 C 0.55774(15) 0.7035(4) 0.5553(2) 0.0265(7) Uani 1 1 d . . . . .
H5 H 0.584267 0.755310 0.523615 0.032 Uiso 1 1 calc R U . . .
C4 C 0.57858(15) 0.6073(4) 0.6339(2) 0.0264(7) Uani 1 1 d . . . . .
H4 H 0.619520 0.594212 0.656437 0.032 Uiso 1 1 calc R U . . .
C8 C 0.29338(15) 0.9293(4) 0.5502(2) 0.0225(6) Uani 1 1 d . . . . .
C13 C 0.06881(16) 0.4061(4) 0.5952(2) 0.0277(7) Uani 1 1 d . . . . .
C12 C 0.26826(15) 0.6646(4) 0.5105(2) 0.0243(7) Uani 1 1 d . . . . .
C11 C 0.21051(15) 0.7091(4) 0.4738(2) 0.0298(7) Uani 1 1 d . . . . .
H11 H 0.181692 0.633203 0.449481 0.036 Uiso 1 1 calc R U . . .
C9 C 0.23675(16) 0.9764(4) 0.5118(2) 0.0284(7) Uani 1 1 d . . . . .
H9 H 0.226321 1.083027 0.511943 0.034 Uiso 1 1 calc R U . . .
N3 N 0.1265(6) 0.4572(11) 0.6250(10) 0.030(2) Uani 0.555(14) 1 d . . P A 1
C18 C 0.02119(16) 0.4162(4) 0.6403(2) 0.0277(7) Uani 1 1 d . . . . .
C14 C 0.06273(16) 0.3096(4) 0.5140(2) 0.0294(7) Uani 1 1 d . . . . .
C21 C 0.2592(9) 0.825(2) 0.760(2) 0.029(3) Uani 0.555(14) 1 d . U P A 1
H21 H 0.267771 0.933378 0.760020 0.035 Uiso 0.555(14) 1 calc R U P A 1
C19 C 0.1914(7) 0.6230(16) 0.7191(14) 0.029(2) Uani 0.555(14) 1 d . U P A 1
C17 C -0.03016(17) 0.3354(4) 0.6059(3) 0.0326(8) Uani 1 1 d . . . . .
H17 H -0.062340 0.345714 0.636820 0.039 Uiso 1 1 calc R U . . .
C10 C 0.19540(16) 0.8657(5) 0.4731(3) 0.0325(8) Uani 1 1 d . . . . .
H10 H 0.156455 0.896828 0.445869 0.039 Uiso 1 1 calc R U . . .
C15 C 0.01210(18) 0.2272(4) 0.4798(3) 0.0335(8) Uani 1 1 d . . . . .
H15 H 0.009051 0.162264 0.424790 0.040 Uiso 1 1 calc R U . . .
C16 C -0.03438(18) 0.2395(5) 0.5262(3) 0.0369(9) Uani 1 1 d . . . . .
H16 H -0.069214 0.182017 0.503296 0.044 Uiso 1 1 calc R U . . .
C20 C 0.2026(10) 0.7821(18) 0.728(2) 0.029(3) Uani 0.555(14) 1 d . U P A 1
C23 C 0.2958(9) 0.5674(16) 0.7904(16) 0.031(3) Uani 0.555(14) 1 d . U P A 1
H23 H 0.326806 0.496984 0.813890 0.037 Uiso 0.555(14) 1 calc R U P A 1
C22 C 0.3050(8) 0.7256(16) 0.7914(16) 0.027(2) Uani 0.555(14) 1 d . U P A 1
H22 H 0.343302 0.765797 0.814174 0.033 Uiso 0.555(14) 1 calc R U P A 1
C24 C 0.2383(6) 0.514(2) 0.7528(12) 0.030(2) Uani 0.555(14) 1 d . U P A 1
N4 N 0.1320(3) 0.5731(10) 0.6788(6) 0.0320(18) Uani 0.555(14) 1 d . U P A 1
N4A N 0.1443(4) 0.5006(12) 0.7056(6) 0.027(2) Uani 0.445(14) 1 d . U P A 2
N3A N 0.1203(7) 0.5117(12) 0.6215(11) 0.023(2) Uani 0.445(14) 1 d . . P A 2
Br8A Br 0.2468(3) 0.2944(5) 0.7774(5) 0.0523(8) Uani 0.445(14) 1 d . U P A 2
C24A C 0.2504(8) 0.521(3) 0.7665(16) 0.029(3) Uani 0.445(14) 1 d . U P A 2
C19A C 0.1970(9) 0.5912(18) 0.7269(16) 0.024(2) Uani 0.445(14) 1 d . U P A 2
C20A C 0.2002(11) 0.753(2) 0.727(2) 0.022(3) Uani 0.445(14) 1 d . U P A 2
C21A C 0.2517(10) 0.847(3) 0.759(3) 0.027(3) Uani 0.445(14) 1 d . U P A 2
H21A H 0.251028 0.957749 0.756527 0.032 Uiso 0.445(14) 1 calc R U P A 2
C22A C 0.3017(11) 0.764(2) 0.793(2) 0.028(3) Uani 0.445(14) 1 d . U P A 2
H22A H 0.337766 0.816253 0.815268 0.034 Uiso 0.445(14) 1 calc R U P A 2
C23A C 0.2995(11) 0.604(2) 0.795(2) 0.030(3) Uani 0.445(14) 1 d . U P A 2
H23A H 0.334968 0.548900 0.817118 0.036 Uiso 0.445(14) 1 calc R U P A 2
Br7A Br 0.13140(18) 0.8757(8) 0.6957(2) 0.0359(6) Uani 0.445(14) 1 d . U P A 2


_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 C2 1.898(3) . ?
Br2 C6 1.898(3) . ?
Br3 C8 1.892(3) . ?
Br4 C12 1.888(3) . ?
Br5 C14 1.895(4) . ?
Br6 C18 1.897(3) . ?
Br7 C20 1.90(2) . ?
Br8 C24 1.84(2) . ?
N1 N2 1.241(4) . ?
N1 C1 1.436(4) . ?
N2 C7 1.452(4) . ?
C1 C2 1.399(4) . ?
C1 C6 1.397(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.380(5) . ?
C3 C4 1.397(5) . ?
C7 C8 1.396(4) . ?
C7 C12 1.387(5) . ?
C6 C5 1.384(5) . ?
C5 H5 0.9500 . ?
C5 C4 1.391(5) . ?
C4 H4 0.9500 . ?
C8 C9 1.382(5) . ?
C13 N3 1.398(14) . ?
C13 C18 1.398(5) . ?
C13 C14 1.402(5) . ?
C13 N3A 1.492(14) . ?
C12 C11 1.395(5) . ?
C11 H11 0.9500 . ?
C11 C10 1.393(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(5) . ?
N3 N4 1.246(13) . ?
C18 C17 1.385(5) . ?
C14 C15 1.378(5) . ?
C21 H21 0.9500 . ?
C21 C20 1.36(3) . ?
C21 C22 1.374(16) . ?
C19 C20 1.395(15) . ?
C19 C24 1.445(18) . ?
C19 N4 1.452(17) . ?
C17 H17 0.9500 . ?
C17 C16 1.387(5) . ?
C10 H10 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.386(6) . ?
C16 H16 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.379(13) . ?
C23 C24 1.414(17) . ?
C22 H22 0.9500 . ?
N4A N3A 1.209(19) . ?
N4A C19A 1.44(2) . ?
Br8A C24A 1.96(2) . ?
C24A C19A 1.39(2) . ?
C24A C23A 1.34(2) . ?
C19A C20A 1.397(18) . ?
C20A C21A 1.44(3) . ?
C20A Br7A 1.90(3) . ?
C21A H21A 0.9500 . ?
C21A C22A 1.37(2) . ?
C22A H22A 0.9500 . ?
C22A C23A 1.381(16) . ?
C23A H23A 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
N2 N1 C1 112.7(3) . . ?
N1 N2 C7 112.4(3) . . ?
C2 C1 N1 125.2(3) . . ?
C6 C1 N1 117.3(3) . . ?
C6 C1 C2 117.4(3) . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C8 C7 N2 116.6(3) . . ?
C12 C7 N2 124.9(3) . . ?
C12 C7 C8 118.4(3) . . ?
C1 C2 Br1 120.9(2) . . ?
C3 C2 Br1 117.3(2) . . ?
C3 C2 C1 121.7(3) . . ?
C1 C6 Br2 119.0(2) . . ?
C5 C6 Br2 119.2(2) . . ?
C5 C6 C1 121.8(3) . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C7 C8 Br3 119.4(2) . . ?
C9 C8 Br3 118.8(2) . . ?
C9 C8 C7 121.8(3) . . ?
N3 C13 C18 130.8(6) . . ?
N3 C13 C14 111.1(6) . . ?
C18 C13 C14 117.3(3) . . ?
C18 C13 N3A 121.7(6) . . ?
C14 C13 N3A 120.3(7) . . ?
C7 C12 Br4 121.4(3) . . ?
C7 C12 C11 120.7(3) . . ?
C11 C12 Br4 117.9(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
N4 N3 C13 113.9(10) . . ?
C13 C18 Br6 122.9(3) . . ?
C17 C18 Br6 115.6(3) . . ?
C17 C18 C13 121.5(3) . . ?
C13 C14 Br5 120.1(3) . . ?
C15 C14 Br5 118.1(3) . . ?
C15 C14 C13 121.7(3) . . ?
C20 C21 H21 117.4 . . ?
C20 C21 C22 125(2) . . ?
C22 C21 H21 117.4 . . ?
C20 C19 C24 119.4(17) . . ?
C20 C19 N4 118.2(12) . . ?
C24 C19 N4 122.4(12) . . ?
C18 C17 H17 120.2 . . ?
C18 C17 C16 119.6(4) . . ?
C16 C17 H17 120.2 . . ?
C11 C10 H10 119.7 . . ?
C9 C10 C11 120.5(3) . . ?
C9 C10 H10 119.7 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.6(4) . . ?
C16 C15 H15 120.2 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.2(4) . . ?
C15 C16 H16 119.9 . . ?
C21 C20 Br7 124.0(14) . . ?
C21 C20 C19 117(2) . . ?
C19 C20 Br7 119.2(14) . . ?
C22 C23 H23 121.4 . . ?
C22 C23 C24 117.3(16) . . ?
C24 C23 H23 121.4 . . ?
C21 C22 C23 120.3(15) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C19 C24 Br8 124.2(10) . . ?
C23 C24 Br8 115.0(12) . . ?
C23 C24 C19 120.6(17) . . ?
N3 N4 C19 116.4(10) . . ?
N3A N4A C19A 111.4(12) . . ?
N4A N3A C13 112.4(11) . . ?
C19A C24A Br8A 114.4(14) . . ?
C23A C24A Br8A 123.7(15) . . ?
C23A C24A C19A 122(2) . . ?
C24A C19A N4A 120.4(15) . . ?
C24A C19A C20A 113(2) . . ?
C20A C19A N4A 125.8(16) . . ?
C19A C20A C21A 127(2) . . ?
C19A C20A Br7A 120.9(16) . . ?
C21A C20A Br7A 111.8(16) . . ?
C20A C21A H21A 122.9 . . ?
C22A C21A C20A 114(2) . . ?
C22A C21A H21A 122.9 . . ?
C21A C22A H22A 120.1 . . ?
C21A C22A C23A 119.9(19) . . ?
C23A C22A H22A 120.1 . . ?
C24A C23A C22A 124(2) . . ?
C24A C23A H23A 118.0 . . ?
C22A C23A H23A 118.0 . . ?

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
Br2 C6 C5 C4 -178.4(2) . . . . ?
Br3 C8 C9 C10 179.9(3) . . . . ?
Br4 C12 C11 C10 -179.8(3) . . . . ?
Br5 C14 C15 C16 -177.3(3) . . . . ?
Br6 C18 C17 C16 179.9(3) . . . . ?
N1 N2 C7 C8 -121.3(3) . . . . ?
N1 N2 C7 C12 61.8(4) . . . . ?
N1 C1 C2 Br1 2.3(4) . . . . ?
N1 C1 C2 C3 178.3(3) . . . . ?
N1 C1 C6 Br2 0.8(4) . . . . ?
N1 C1 C6 C5 -179.3(3) . . . . ?
N2 N1 C1 C2 63.4(4) . . . . ?
N2 N1 C1 C6 -121.0(3) . . . . ?
N2 C7 C8 Br3 1.9(4) . . . . ?
N2 C7 C8 C9 179.6(3) . . . . ?
N2 C7 C12 Br4 -0.6(4) . . . . ?
N2 C7 C12 C11 178.4(3) . . . . ?
C1 N1 N2 C7 176.6(2) . . . . ?
C1 C6 C5 C4 1.7(5) . . . . ?
C7 C8 C9 C10 2.2(5) . . . . ?
C7 C12 C11 C10 1.3(5) . . . . ?
C2 C1 C6 Br2 176.8(2) . . . . ?
C2 C1 C6 C5 -3.3(4) . . . . ?
C2 C3 C4 C5 -1.4(5) . . . . ?
C6 C1 C2 Br1 -173.3(2) . . . . ?
C6 C1 C2 C3 2.6(4) . . . . ?
C6 C5 C4 C3 0.7(5) . . . . ?
C4 C3 C2 Br1 175.8(2) . . . . ?
C4 C3 C2 C1 -0.3(5) . . . . ?
C8 C7 C12 Br4 -177.4(2) . . . . ?
C8 C7 C12 C11 1.6(4) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C13 N3 N4 C19 174.6(10) . . . . ?
C13 C18 C17 C16 1.4(5) . . . . ?
C13 C14 C15 C16 0.2(6) . . . . ?
C12 C7 C8 Br3 179.0(2) . . . . ?
C12 C7 C8 C9 -3.4(5) . . . . ?
C12 C11 C10 C9 -2.4(5) . . . . ?
N3 C13 C18 Br6 12.5(8) . . . . ?
N3 C13 C18 C17 -169.1(7) . . . . ?
N3 C13 C14 Br5 -12.1(6) . . . . ?
N3 C13 C14 C15 170.5(6) . . . . ?
C18 C13 N3 N4 -29.0(15) . . . . ?
C18 C13 C14 Br5 177.2(3) . . . . ?
C18 C13 C14 C15 -0.3(5) . . . . ?
C18 C13 N3A N4A 59.7(13) . . . . ?
C18 C17 C16 C15 -1.5(6) . . . . ?
C14 C13 N3 N4 161.8(9) . . . . ?
C14 C13 C18 Br6 -179.0(2) . . . . ?
C14 C13 C18 C17 -0.6(5) . . . . ?
C14 C13 N3A N4A -130.2(11) . . . . ?
C14 C15 C16 C17 0.7(6) . . . . ?
C20 C21 C22 C23 2(4) . . . . ?
C20 C19 C24 Br8 172.3(17) . . . . ?
C20 C19 C24 C23 -3(3) . . . . ?
C20 C19 N4 N3 142.4(18) . . . . ?
C22 C21 C20 Br7 174.1(18) . . . . ?
C22 C21 C20 C19 -6(4) . . . . ?
C22 C23 C24 Br8 -177.0(14) . . . . ?
C22 C23 C24 C19 -1(2) . . . . ?
C24 C19 C20 Br7 -173.6(16) . . . . ?
C24 C19 C20 C21 7(3) . . . . ?
C24 C19 N4 N3 -40(2) . . . . ?
C24 C23 C22 C21 2(2) . . . . ?
N4 C19 C20 Br7 4(3) . . . . ?
N4 C19 C20 C21 -176(2) . . . . ?
N4 C19 C24 Br8 -6(2) . . . . ?
N4 C19 C24 C23 179.1(16) . . . . ?
N4A C19A C20A C21A 172(3) . . . . ?
N4A C19A C20A Br7A -1(3) . . . . ?
N3A C13 C18 Br6 -8.6(8) . . . . ?
N3A C13 C18 C17 169.8(7) . . . . ?
N3A C13 C14 Br5 6.6(7) . . . . ?
N3A C13 C14 C15 -170.8(7) . . . . ?
N3A N4A C19A C24A -123(2) . . . . ?
N3A N4A C19A C20A 68(2) . . . . ?
Br8A C24A C19A N4A 5(2) . . . . ?
Br8A C24A C19A C20A 175.4(18) . . . . ?
Br8A C24A C23A C22A -175.7(19) . . . . ?
C24A C19A C20A C21A 3(4) . . . . ?
C24A C19A C20A Br7A -170(2) . . . . ?
C19A N4A N3A C13 174.1(10) . . . . ?
C19A C24A C23A C22A 4(3) . . . . ?
C19A C20A C21A C22A -1(5) . . . . ?
C20A C21A C22A C23A 0(4) . . . . ?
C21A C22A C23A C24A -2(3) . . . . ?
C23A C24A C19A N4A -174(2) . . . . ?
C23A C24A C19A C20A -4(3) . . . . ?
Br7A C20A C21A C22A 172.9(19) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.277
_oxdiff_exptl_absorpt_empirical_full_min 0.516
