# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2328821'
loop_
_audit_author_name
_audit_author_address
'Ji Kangyu'
;North China Electric Power University
China
;
_audit_update_record             
;
2024-01-27 deposited with the CCDC.	2024-03-05 downloaded from the CCDC.
;
_audit_creation_date             2023-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Br6, 3(C H5 N2)'
_chemical_formula_sum            'C3 H15 Bi Br6 N6'
_chemical_formula_weight         823.65
_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'
Bi Bi -4.1077 10.2566 '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      tetragonal
_space_group_IT_number           84
_space_group_name_H-M_alt        'P 42/m'
_space_group_name_Hall           '-P 4c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z+1/2'
'y, -x, z+1/2'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z-1/2'
'-y, x, -z-1/2'

_cell_length_a                   10.3603(6)
_cell_length_b                   10.3603(6)
_cell_length_c                   9.0922(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     975.92(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5431
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      24.31
_cell_measurement_theta_min      2.78
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    21.305
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.2425
_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_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.803
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1223
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27474
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.527
_diffrn_reflns_theta_min         2.780
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                925
_reflns_number_total             1577
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.927
_refine_diff_density_rms         0.190
_refine_ls_extinction_coef       0.0154(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1577
_refine_ls_number_restraints     64
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.021
_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)+(0.0543P)²+0.9404P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1175
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 C1-N1
 1.4 with sigma of 0.01
 C1-N2
 1.35 with sigma of 0.01
 C2-N4
 1.35 with sigma of 0.01
 C2-N3
 1.4 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
N3 \\sim N4 \\sim C2: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
N1 \\sim N2 \\sim C1: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02 within 2A
Uanis(N4) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 N1, N2, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 N3, N4, C2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
5. Others
 Fixed Sof: N1(0.5) H1A(0.5) H1B(0.5) N2(0.5) H2A(0.5) H2B(0.5) C1(0.5)
 H1(0.5) N3(0.25) H3A(0.25) H3B(0.25) N4(0.25) H4A(0.25) H4B(0.25) C2(0.25)
 H2(0.25)
 Fixed Z: N3(0.50875)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
6.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B)
;
_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
Bi1 Bi 0.000000 0.500000 0.500000 0.0580(2) Uani 1 4 d S T P . .
Br1 Br -0.25465(13) 0.60107(15) 0.500000 0.0921(5) Uani 1 2 d S T P . .
Br2 Br 0.07510(11) 0.67816(10) 0.72326(11) 0.0970(4) Uani 1 1 d . . . . .
N1 N 0.387(3) 0.756(2) 0.381(3) 0.127(7) Uani 0.5 1 d D U P A -1
H1A H 0.333822 0.693245 0.368817 0.153 Uiso 0.5 1 calc R U P A -1
H1B H 0.405555 0.806256 0.309013 0.153 Uiso 0.5 1 calc R U P A -1
N2 N 0.414(3) 0.703(3) 0.632(3) 0.137(8) Uani 0.5 1 d D U P A -1
H2A H 0.361046 0.638938 0.622175 0.164 Uiso 0.5 1 calc R U P A -1
H2B H 0.448335 0.717589 0.716595 0.164 Uiso 0.5 1 calc R U P A -1
C1 C 0.441(2) 0.7777(19) 0.518(3) 0.133(6) Uani 0.5 1 d D U P A -1
H1 H 0.497727 0.846324 0.530791 0.160 Uiso 0.5 1 calc R U P A -1
N3 N -0.0823(19) 0.920(2) 0.508750 0.090(6) Uani 0.25 1 d DS U P B -1
H3A H -0.053863 0.864208 0.570923 0.108 Uiso 0.25 1 calc R U P B -1
H3B H -0.156659 0.909109 0.468445 0.108 Uiso 0.25 1 calc R U P B -1
N4 N 0.094(3) 1.002(4) 0.561(4) 0.132(11) Uani 0.25 1 d D U P B -1
H4A H 0.094263 0.933327 0.614088 0.158 Uiso 0.25 1 calc R U P B -1
H4B H 0.159174 1.053472 0.562833 0.158 Uiso 0.25 1 calc R U P B -1
C2 C -0.008(3) 1.028(2) 0.473(4) 0.118(9) Uani 0.25 1 d D U P B -1
H2 H -0.023436 1.096579 0.409414 0.141 Uiso 0.25 1 calc R U P B -1


_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
Bi1 Br1 2.8385(12) . ?
Bi1 Br1 2.8385(12) 5_566 ?
Bi1 Br2 2.8518(8) 2_565 ?
Bi1 Br2 2.8518(8) 5_566 ?
Bi1 Br2 2.8518(8) 6_556 ?
Bi1 Br2 2.8518(8) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C1 1.384(10) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N2 C1 1.327(10) . ?
C1 H1 0.9300 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C2 1.4000(11) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C2 1.350(10) . ?
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
Br1 Bi1 Br1 180.0 . 5_566 ?
Br1 Bi1 Br2 89.15(3) 5_566 6_556 ?
Br1 Bi1 Br2 90.85(3) 5_566 2_565 ?
Br1 Bi1 Br2 90.85(3) 5_566 5_566 ?
Br1 Bi1 Br2 89.15(3) 5_566 . ?
Br1 Bi1 Br2 89.15(3) . 2_565 ?
Br1 Bi1 Br2 90.85(3) . 6_556 ?
Br1 Bi1 Br2 90.85(3) . . ?
Br1 Bi1 Br2 89.15(3) . 5_566 ?
Br2 Bi1 Br2 180.00(3) 6_556 2_565 ?
Br2 Bi1 Br2 90.76(5) . 6_556 ?
Br2 Bi1 Br2 89.24(5) . 2_565 ?
Br2 Bi1 Br2 89.24(5) 5_566 6_556 ?
Br2 Bi1 Br2 90.76(5) 5_566 2_565 ?
Br2 Bi1 Br2 180.0 . 5_566 ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
N1 C1 H1 119.3 . . ?
N2 C1 N1 121(2) . . ?
N2 C1 H1 119.2 . . ?
H3A N3 H3B 120.0 . . ?
C2 N3 H3A 120.0 . . ?
C2 N3 H3B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N4 H4A 120.0 . . ?
C2 N4 H4B 120.0 . . ?
N3 C2 H2 131.2 . . ?
N4 C2 N3 98(2) . . ?
N4 C2 H2 131.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
