# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_bb125_1_p_1
_database_code_depnum_ccdc_archive 'CCDC 2293844'
loop_
_audit_author_name
_audit_author_address
'Biswajit Bhattacharya'
;BAM Federal Institute for Materials Research and Testing
Germany
;
_audit_update_record             
;
2023-09-27 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2021-11-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H14 Br2 N2'
_chemical_formula_sum            'C24 H14 Br2 N2'
_chemical_formula_weight         490.19
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.8937(2)
_cell_length_b                   5.8230(4)
_cell_length_c                   21.4091(12)
_cell_angle_alpha                88.194(2)
_cell_angle_beta                 84.820(2)
_cell_angle_gamma                87.628(2)
_cell_volume                     482.82(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    450
_cell_measurement_temperature    152.00
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   0.538
_shelx_estimated_absorpt_T_min   0.220
_exptl_absorpt_coefficient_mu    4.209
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             242
_exptl_crystal_size_max          0.515
_exptl_crystal_size_mid          0.349
_exptl_crystal_size_min          0.168
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12660
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.766
_diffrn_reflns_theta_min         2.867
_diffrn_ambient_temperature      152.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1893
_reflns_number_total             2030
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2030
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.174
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0205P)²+0.9122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0866
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C7(H7), C3(H3), C6(H6), C10(H10), C2(H2)
;
_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 0.76669(10) 0.76324(7) 0.04862(2) 0.04227(14) Uani 1 1 d . . . . .
N1 N 0.6681(8) 0.0967(4) 0.34987(13) 0.0320(6) Uani 1 1 d . . . . .
C9 C 0.1409(8) 0.4856(5) 0.43673(14) 0.0230(6) Uani 1 1 d . . . . .
C1 C 0.3685(8) 0.6405(5) 0.25925(14) 0.0226(6) Uani 1 1 d . . . . .
C5 C 0.4044(9) 0.8830(5) 0.16459(15) 0.0300(7) Uani 1 1 d . . . . .
H5 H 0.3500 1.0243 0.1437 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5969(8) 0.7115(6) 0.13303(14) 0.0279(7) Uani 1 1 d . . . . .
C11 C -0.1776(8) 0.6961(5) 0.51969(15) 0.0269(6) Uani 1 1 d . . . . .
H11 H -0.3011 0.8328 0.5329 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2416(8) 0.6268(5) 0.32521(14) 0.0243(6) Uani 1 1 d . . . . .
H7 H 0.0968 0.7544 0.3387 0.029 Uiso 1 1 calc R U . . .
C8 C 0.2910(8) 0.4666(5) 0.37106(14) 0.0227(6) Uani 1 1 d . . . . .
C3 C 0.6723(9) 0.5047(6) 0.16281(15) 0.0312(7) Uani 1 1 d . . . . .
H3 H 0.8016 0.3867 0.1405 0.037 Uiso 1 1 calc R U . . .
C12 C 0.5018(8) 0.2617(5) 0.35795(14) 0.0241(6) Uani 1 1 d . . . . .
C6 C 0.2921(8) 0.8466(5) 0.22686(15) 0.0274(6) Uani 1 1 d . . . . .
H6 H 0.1590 0.9646 0.2485 0.033 Uiso 1 1 calc R U . . .
C10 C -0.0409(9) 0.6834(5) 0.45846(15) 0.0275(7) Uani 1 1 d . . . . .
H10 H -0.0704 0.8110 0.4304 0.033 Uiso 1 1 calc R U . . .
C2 C 0.5591(8) 0.4695(5) 0.22526(15) 0.0289(7) Uani 1 1 d . . . . .
H2 H 0.6116 0.3266 0.2455 0.035 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 C4 1.887(3) . ?
N1 C12 1.145(4) . ?
C9 C11 1.400(4) 2_566 ?
C9 C8 1.479(4) . ?
C9 C10 1.396(4) . ?
C1 C7 1.454(4) . ?
C1 C6 1.402(4) . ?
C1 C2 1.399(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.380(5) . ?
C5 C6 1.378(4) . ?
C4 C3 1.378(5) . ?
C11 C9 1.400(4) 2_566 ?
C11 H11 0.9500 . ?
C11 C10 1.373(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.354(4) . ?
C8 C12 1.440(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.381(4) . ?
C6 H6 0.9500 . ?
C10 H10 0.9500 . ?
C2 H2 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
C11 C9 C8 120.9(3) 2_566 . ?
C10 C9 C11 116.9(3) . 2_566 ?
C10 C9 C8 122.3(3) . . ?
C6 C1 C7 116.3(3) . . ?
C2 C1 C7 126.6(3) . . ?
C2 C1 C6 117.1(3) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C6 C5 C4 119.1(3) . . ?
C5 C4 Br1 119.6(2) . . ?
C3 C4 Br1 119.6(2) . . ?
C3 C4 C5 120.8(3) . . ?
C9 C11 H11 118.9 2_566 . ?
C10 C11 C9 122.1(3) . 2_566 ?
C10 C11 H11 118.9 . . ?
C1 C7 H7 113.9 . . ?
C8 C7 C1 132.1(3) . . ?
C8 C7 H7 113.9 . . ?
C7 C8 C9 124.1(3) . . ?
C7 C8 C12 120.6(3) . . ?
C12 C8 C9 115.3(3) . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
N1 C12 C8 177.4(3) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 C1 121.9(3) . . ?
C5 C6 H6 119.0 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.4 . . ?

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 C4 C3 C2 177.6(3) . . . . ?
C9 C11 C10 C9 0.4(6) 2_566 . . . ?
C1 C7 C8 C9 179.1(3) . . . . ?
C1 C7 C8 C12 -0.6(5) . . . . ?
C5 C4 C3 C2 -1.1(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C3 C2 C1 -0.1(5) . . . . ?
C11 C9 C8 C7 174.2(3) 2_566 . . . ?
C11 C9 C8 C12 -6.1(4) 2_566 . . . ?
C11 C9 C10 C11 -0.4(5) 2_566 . . . ?
C7 C1 C6 C5 178.5(3) . . . . ?
C7 C1 C2 C3 -178.5(3) . . . . ?
C8 C9 C10 C11 180.0(3) . . . . ?
C6 C1 C7 C8 -173.5(3) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
C6 C5 C4 Br1 -177.7(2) . . . . ?
C6 C5 C4 C3 1.0(5) . . . . ?
C10 C9 C8 C7 -6.1(5) . . . . ?
C10 C9 C8 C12 173.6(3) . . . . ?
C2 C1 C7 C8 6.2(6) . . . . ?
C2 C1 C6 C5 -1.3(5) . . . . ?

_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_DSBr_at_473k
_database_code_depnum_ccdc_archive 'CCDC 2301266'
loop_
_audit_author_name
_audit_author_address
'Subham Ranjan and Prof. Satoshi Takamizawa'
;Yokohama City University
Japan
;
_audit_update_record             
;
2023-10-28 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2023-10-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H14 Br2 N2'
_chemical_formula_sum            'C24 H14 Br2 N2'
_chemical_formula_weight         490.19
_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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   4.113(2)
_cell_length_b                   5.888(4)
_cell_length_c                   21.884(12)
_cell_angle_alpha                93.27(2)
_cell_angle_beta                 92.161(19)
_cell_angle_gamma                94.32(2)
_cell_volume                     527.1(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    373
_cell_measurement_temperature    473(2)
_cell_measurement_theta_max      15.43
_cell_measurement_theta_min      2.80
_exptl_absorpt_coefficient_mu    3.856
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_correction_T_min  0.5213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0941 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.7005.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             242
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            1362
_diffrn_reflns_theta_full        17.71
_diffrn_reflns_theta_max         17.71
_diffrn_reflns_theta_min         1.87
_diffrn_ambient_temperature      473.15
_diffrn_detector_area_resol_mean 7.391
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                393
_reflns_number_total             676
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT (Bruker AXS Inc.)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 97-2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0779
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1868P)²+0.3210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2127
_refine_ls_wR_factor_ref         0.2799
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.068(7) 0.125(4) 0.1722(17) 0.136(8) Uani 1 1 d . . .
H3 H -0.0013 -0.0160 0.1530 0.163 Uiso 1 1 calc R . .
Br1 Br 0.2976(8) 0.2433(7) 0.05488(11) 0.220(3) Uani 1 1 d . . .
N1 N 0.517(5) 0.898(3) 0.3532(8) 0.138(7) Uani 1 1 d . . .
C12 C 0.366(6) 0.731(4) 0.3609(8) 0.090(6) Uani 1 1 d . . .
C4 C 0.219(7) 0.284(7) 0.1371(11) 0.131(8) Uani 1 1 d . . .
C5 C 0.339(6) 0.481(6) 0.1700(15) 0.142(9) Uani 1 1 d . . .
H5 H 0.4588 0.5920 0.1496 0.170 Uiso 1 1 calc R . .
C6 C 0.292(6) 0.522(3) 0.2306(13) 0.118(7) Uani 1 1 d . . .
H6 H 0.3651 0.6615 0.2505 0.142 Uiso 1 1 calc R . .
C7 C 0.071(4) 0.367(3) 0.3267(11) 0.088(6) Uani 1 1 d . . .
H7 H -0.0596 0.2432 0.3391 0.106 Uiso 1 1 calc R . .
C8 C 0.166(4) 0.526(4) 0.3727(10) 0.076(5) Uani 1 1 d . . .
C9 C 0.085(5) 0.515(5) 0.4372(9) 0.073(5) Uani 1 1 d . . .
C10 C 0.158(4) 0.688(3) 0.4837(17) 0.102(6) Uani 1 1 d . . .
H10 H 0.2688 0.8214 0.4724 0.122 Uiso 1 1 calc R . .
C11 C 0.083(6) 0.678(4) 0.5441(14) 0.100(6) Uani 1 1 d . . .
H11 H 0.1454 0.8003 0.5720 0.120 Uiso 1 1 calc R . .
C1 C 0.134(5) 0.354(5) 0.2622(10) 0.090(5) Uani 1 1 d . . .
C2 C 0.012(5) 0.156(4) 0.2309(13) 0.109(7) Uani 1 1 d . . .
H2 H -0.1080 0.0444 0.2508 0.131 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
C3 H3 0.9300 . ?
C3 C4 1.37(3) . ?
C3 C2 1.32(3) . ?
Br1 C4 1.84(2) . ?
N1 C12 1.14(2) . ?
C12 C8 1.45(3) . ?
C4 C5 1.38(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.36(3) . ?
C6 H6 0.9300 . ?
C6 C1 1.37(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.36(2) . ?
C7 C1 1.44(2) . ?
C8 C9 1.47(2) . ?
C9 C10 1.40(2) . ?
C9 C11 1.38(2) 2_566 ?
C10 H10 0.9300 . ?
C10 C11 1.37(2) . ?
C11 C9 1.38(2) 2_566 ?
C11 H11 0.9300 . ?
C1 C2 1.37(2) . ?
C2 H2 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C3 H3 117.2 . . ?
C2 C3 H3 117.2 . . ?
C2 C3 C4 126(2) . . ?
N1 C12 C8 177(2) . . ?
C3 C4 Br1 126(3) . . ?
C3 C4 C5 114(2) . . ?
C5 C4 Br1 120(3) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 C4 123(2) . . ?
C6 C5 H5 118.4 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C1 119.0(19) . . ?
C1 C6 H6 120.5 . . ?
C8 C7 H7 114.0 . . ?
C8 C7 C1 132.0(18) . . ?
C1 C7 H7 114.0 . . ?
C12 C8 C9 113(2) . . ?
C7 C8 C12 121.0(17) . . ?
C7 C8 C9 126(2) . . ?
C10 C9 C8 126(3) . . ?
C11 C9 C8 119(3) 2_566 . ?
C11 C9 C10 114.6(18) 2_566 . ?
C9 C10 H10 116.8 . . ?
C11 C10 C9 126.5(17) . . ?
C11 C10 H10 116.8 . . ?
C9 C11 H11 120.5 2_566 . ?
C10 C11 C9 118.9(16) . 2_566 ?
C10 C11 H11 120.5 . . ?
C6 C1 C7 126(2) . . ?
C2 C1 C6 119.1(18) . . ?
C2 C1 C7 115(2) . . ?
C3 C2 C1 119.0(19) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?

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
C3 C4 C5 C6 -5(4) . . . . ?
Br1 C4 C5 C6 -179.8(19) . . . . ?
N1 C12 C8 C7 141(45) . . . . ?
N1 C12 C8 C9 -38(46) . . . . ?
C12 C8 C9 C10 6(2) . . . . ?
C12 C8 C9 C11 -175.3(16) . . . 2_566 ?
C4 C3 C2 C1 -5(4) . . . . ?
C4 C5 C6 C1 4(4) . . . . ?
C5 C6 C1 C7 178(2) . . . . ?
C5 C6 C1 C2 -4(3) . . . . ?
C6 C1 C2 C3 4(3) . . . . ?
C7 C8 C9 C10 -173.9(16) . . . . ?
C7 C8 C9 C11 5(2) . . . 2_566 ?
C7 C1 C2 C3 -177.6(19) . . . . ?
C8 C7 C1 C6 -6(3) . . . . ?
C8 C7 C1 C2 175.5(16) . . . . ?
C8 C9 C10 C11 180.0(18) . . . . ?
C9 C10 C11 C9 -1(3) . . . 2_566 ?
C11 C9 C10 C11 1(3) 2_566 . . . ?
C1 C7 C8 C12 1(3) . . . . ?
C1 C7 C8 C9 -179.2(17) . . . . ?
C2 C3 C4 Br1 -179.8(18) . . . . ?
C2 C3 C4 C5 5(4) . . . . ?

_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_DSBr_at_293k
_database_code_depnum_ccdc_archive 'CCDC 2301265'
loop_
_audit_author_name
_audit_author_address
'Subham Ranjan and Prof. Satoshi Takamizawa'
;Yokohama City University
Japan
;
_audit_update_record             
;
2023-10-28 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2023-10-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H14 Br2 N2'
_chemical_formula_sum            'C24 H14 Br2 N2'
_chemical_formula_weight         490.19
_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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   3.9746(4)
_cell_length_b                   5.8533(7)
_cell_length_c                   21.594(2)
_cell_angle_alpha                92.010(4)
_cell_angle_beta                 94.227(4)
_cell_angle_gamma                93.104(4)
_cell_volume                     499.89(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1533
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.79
_cell_measurement_theta_min      2.84
_exptl_absorpt_coefficient_mu    4.066
_exptl_absorpt_correction_T_max  0.9087
_exptl_absorpt_correction_T_min  0.1516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             242
_exptl_crystal_size_max          0.745
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.024
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3865
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.84
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 7.391
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1135
_reflns_number_total             1737
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'APEX3 v2019.11 (Bruker AXS Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT (Bruker AXS Inc.)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 97-2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1737
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0409P)²+0.3150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1102
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.31126(16) 0.23854(13) 0.05120(2) 0.0961(4) Uani 1 1 d . . .
C8 C 0.1666(9) 0.5322(6) 0.37230(18) 0.0361(9) Uani 1 1 d . . .
N1 N 0.5188(10) 0.8990(7) 0.35157(18) 0.0588(10) Uani 1 1 d . . .
C9 C 0.0792(9) 0.5143(6) 0.43722(19) 0.0367(9) Uani 1 1 d . . .
C1 C 0.1320(10) 0.3571(6) 0.26100(19) 0.0414(10) Uani 1 1 d . . .
C12 C 0.3617(11) 0.7358(7) 0.35917(18) 0.0421(10) Uani 1 1 d . . .
C7 C 0.0714(11) 0.3728(7) 0.32666(19) 0.0408(10) Uani 1 1 d . . .
C10 C 0.1586(11) 0.6938(7) 0.4811(2) 0.0457(11) Uani 1 1 d . . .
C11 C 0.0815(11) 0.6795(7) 0.5412(2) 0.0477(11) Uani 1 1 d . . .
C2 C 0.0239(12) 0.1565(8) 0.2282(2) 0.0504(11) Uani 1 1 d . . .
C4 C 0.2309(11) 0.2881(9) 0.1355(2) 0.0554(12) Uani 1 1 d . . .
C3 C 0.0725(13) 0.1208(9) 0.1667(2) 0.0578(13) Uani 1 1 d . . .
C6 C 0.2903(12) 0.5252(9) 0.2275(2) 0.0544(13) Uani 1 1 d . . .
C5 C 0.3401(13) 0.4893(10) 0.1660(2) 0.0628(14) Uani 1 1 d . . .
H7 H -0.074(10) 0.245(7) 0.3390(18) 0.048(12) Uiso 1 1 d . . .
H6 H 0.373(10) 0.654(7) 0.2428(18) 0.043(12) Uiso 1 1 d . . .
H11 H 0.123(10) 0.806(7) 0.5683(19) 0.048(11) Uiso 1 1 d . . .
H5 H 0.429(11) 0.593(8) 0.147(2) 0.058(15) Uiso 1 1 d . . .
H10 H 0.260(10) 0.828(7) 0.4680(18) 0.048(12) Uiso 1 1 d . . .
H3 H -0.011(11) -0.002(8) 0.150(2) 0.058(14) Uiso 1 1 d . . .
H2 H -0.075(11) 0.040(8) 0.248(2) 0.061(15) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.887(4) . ?
C8 C9 1.475(6) . ?
C8 C12 1.435(6) . ?
C8 C7 1.352(5) . ?
N1 C12 1.136(5) . ?
C9 C10 1.398(5) . ?
C9 C11 1.384(6) 2_566 ?
C1 C7 1.456(6) . ?
C1 C2 1.381(6) . ?
C1 C6 1.391(6) . ?
C7 H7 0.98(4) . ?
C10 C11 1.358(6) . ?
C10 H10 0.93(4) . ?
C11 C9 1.384(6) 2_566 ?
C11 H11 0.93(4) . ?
C2 C3 1.365(6) . ?
C2 H2 0.90(5) . ?
C4 C3 1.361(7) . ?
C4 C5 1.362(7) . ?
C3 H3 0.83(5) . ?
C6 C5 1.369(7) . ?
C6 H6 0.85(4) . ?
C5 H5 0.83(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C8 C9 115.5(3) . . ?
C7 C8 C9 124.0(4) . . ?
C7 C8 C12 120.4(4) . . ?
C10 C9 C8 121.4(4) . . ?
C11 C9 C8 122.8(3) 2_566 . ?
C11 C9 C10 115.8(4) 2_566 . ?
C2 C1 C7 117.5(4) . . ?
C2 C1 C6 116.1(4) . . ?
C6 C1 C7 126.4(4) . . ?
N1 C12 C8 176.9(4) . . ?
C8 C7 C1 132.5(4) . . ?
C8 C7 H7 115(2) . . ?
C1 C7 H7 113(2) . . ?
C9 C10 H10 118(3) . . ?
C11 C10 C9 122.1(4) . . ?
C11 C10 H10 120(3) . . ?
C9 C11 H11 118(2) 2_566 . ?
C10 C11 C9 122.1(4) . 2_566 ?
C10 C11 H11 120(3) . . ?
C1 C2 H2 120(3) . . ?
C3 C2 C1 122.7(5) . . ?
C3 C2 H2 117(3) . . ?
C3 C4 Br1 120.2(4) . . ?
C3 C4 C5 119.6(5) . . ?
C5 C4 Br1 120.1(4) . . ?
C2 C3 H3 117(3) . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 123(3) . . ?
C1 C6 H6 125(3) . . ?
C5 C6 C1 121.2(5) . . ?
C5 C6 H6 114(3) . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 120(3) . . ?
C6 C5 H5 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 C4 C3 C2 178.2(4) . . . . ?
Br1 C4 C5 C6 -178.5(4) . . . . ?
C8 C9 C10 C11 -179.6(4) . . . . ?
C9 C8 C12 N1 12(8) . . . . ?
C9 C8 C7 C1 -179.4(4) . . . . ?
C9 C10 C11 C9 0.3(8) . . . 2_566 ?
C1 C2 C3 C4 -0.5(8) . . . . ?
C1 C6 C5 C4 0.9(8) . . . . ?
C12 C8 C9 C10 5.2(5) . . . . ?
C12 C8 C9 C11 -174.1(4) . . . 2_566 ?
C12 C8 C7 C1 1.3(7) . . . . ?
C7 C8 C9 C10 -174.2(4) . . . . ?
C7 C8 C9 C11 6.6(6) . . . 2_566 ?
C7 C8 C12 N1 -168(8) . . . . ?
C7 C1 C2 C3 -178.8(4) . . . . ?
C7 C1 C6 C5 178.6(4) . . . . ?
C11 C9 C10 C11 -0.3(7) 2_566 . . . ?
C2 C1 C7 C8 173.7(4) . . . . ?
C2 C1 C6 C5 -1.2(7) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
C6 C1 C7 C8 -6.1(8) . . . . ?
C6 C1 C2 C3 1.0(7) . . . . ?
C5 C4 C3 C2 0.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
