# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_c-659-Cl
_database_code_depnum_ccdc_archive 'CCDC 2171465'
loop_
_audit_author_name
_audit_author_address
'Chengmin Ji' 'FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE'
_audit_update_record             
;
2022-05-09 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_audit_creation_date             2022-05-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'Bi Cl5, 2(C5 H13 N)'
_chemical_formula_sum            'C10 H26 Bi Cl5 N2'
_chemical_formula_weight         560.57
_chemical_oxdiff_formula         'C H N Bi Cl'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.98376 10.58997 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   5.56500(10)
_cell_length_b                   18.5529(5)
_cell_length_c                   18.7630(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.124(2)
_cell_angle_gamma                90
_cell_volume                     1922.27(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6497
_cell_measurement_temperature    229.7(7)
_cell_measurement_theta_max      28.9730
_cell_measurement_theta_min      3.8820
_exptl_absorpt_coefficient_mu    9.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.9368
_exptl_crystal_F_000             1059.9641
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12886
_diffrn_reflns_theta_full        26.3674
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.46
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      229.7(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9985
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   90.00   1.0000    2.9600
omega____ theta____ kappa____ phi______ frames
    -       11.3879   77.0000   90.0000 112

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00   90.00   1.0000    2.9600
omega____ theta____ kappa____ phi______ frames
    -       11.3879   77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
  3 omega   34.00   71.00   1.0000    2.9600
omega____ theta____ kappa____ phi______ frames
    -       11.3879 -178.0000  150.0000 37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1250006000
_diffrn_orient_matrix_UB_12      -0.0074923000
_diffrn_orient_matrix_UB_13      -0.0000293000
_diffrn_orient_matrix_UB_21      -0.0295586000
_diffrn_orient_matrix_UB_22      0.0306785000
_diffrn_orient_matrix_UB_23      -0.0218953000
_diffrn_orient_matrix_UB_31      0.0014275000
_diffrn_orient_matrix_UB_32      -0.0215460000
_diffrn_orient_matrix_UB_33      -0.0311748000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -6
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3438
_reflns_number_total             3903
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         1.1718
_refine_diff_density_min         -3.6648
_refine_diff_density_rms         0.3724
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             5.8855
_refine_ls_goodness_of_fit_ref   0.9305
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      0.9305
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0761P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.1021
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2), N1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C9(H9a,H9b), C10(H10a,H10b), C4(H4a,H4b), C3(H3a,H3b), C5(H5a,H5b)
2.c Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C7(H7a,H7b,H7c), C2(H2a,H2b,H2c), C1(H1a,H1b,H1c)
;
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_refinement_flags_posn
Bi1 Bi 0.11512(3) 0.782379(11) 0.224430(10) 0.01337(11) Uani 1.000000 .
Cl4 Cl 0.1776(3) 0.68416(9) 0.33572(8) 0.0280(4) Uani 1.000000 .
Cl3 Cl 0.1422(3) 0.88848(9) 0.31541(9) 0.0302(4) Uani 1.000000 .
Cl1 Cl 0.0788(3) 0.66431(8) 0.13028(8) 0.0241(3) Uani 1.000000 .
Cl2 Cl 0.0587(3) 0.86657(9) 0.11246(9) 0.0330(4) Uani 1.000000 .
Cl5 Cl 0.5736(3) 0.78344(10) 0.22645(11) 0.0422(6) Uani 1.000000 .
N2 N 0.4792(8) 0.5577(3) 0.2726(3) 0.0202(10) Uani 1.000000 .
H2 H 0.3809(8) 0.5965(3) 0.2814(3) 0.0243(13) Uiso 1.000000 R
C8 C 0.6160(11) 0.5365(4) 0.3433(3) 0.0306(15) Uani 1.000000 .
H8a H 0.7285(11) 0.4968(4) 0.3355(3) 0.0367(18) Uiso 1.000000 R
H8b H 0.7140(11) 0.5780(4) 0.3633(3) 0.0367(18) Uiso 1.000000 R
C9 C 0.4510(13) 0.5126(4) 0.3969(4) 0.0342(16) Uani 1.000000 .
H9a H 0.3124(13) 0.5463(4) 0.3953(4) 0.0410(19) Uiso 1.000000 R
H9b H 0.3863(13) 0.4641(4) 0.3835(4) 0.0410(19) Uiso 1.000000 R
C6 C 0.6479(11) 0.5837(4) 0.2221(3) 0.0283(15) Uani 1.000000 .
H6a H 0.750(5) 0.5436(6) 0.2099(17) 0.042(2) Uiso 1.000000 GR
H6b H 0.5539(11) 0.602(2) 0.1783(10) 0.042(2) Uiso 1.000000 GR
H6c H 0.750(5) 0.6222(15) 0.2450(9) 0.042(2) Uiso 1.000000 GR
C7 C 0.3191(11) 0.5007(4) 0.2385(4) 0.0326(16) Uani 1.000000 .
H7a H 0.4151(17) 0.4576(9) 0.232(2) 0.049(2) Uiso 1.000000 GR
H7b H 0.195(5) 0.4891(17) 0.2694(12) 0.049(2) Uiso 1.000000 GR
H7c H 0.241(6) 0.5177(10) 0.1918(11) 0.049(2) Uiso 1.000000 GR
C10 C 0.5817(13) 0.5103(4) 0.4725(3) 0.0356(17) Uani 1.000000 .
H10a H 0.7161(13) 0.4751(4) 0.4743(3) 0.043(2) Uiso 1.000000 R
H10b H 0.6529(13) 0.5583(4) 0.4848(3) 0.043(2) Uiso 1.000000 R
N1 N -0.3268(10) 0.7149(3) 0.0031(3) 0.0240(13) Uani 1.000000 .
H1 H -0.2126(10) 0.7049(3) 0.0424(3) 0.0288(15) Uiso 1.000000 R
C4 C -0.3125(13) 0.5835(4) -0.0280(4) 0.0408(18) Uani 1.000000 .
H4a H -0.2401(13) 0.5914(4) -0.0730(4) 0.049(2) Uiso 1.000000 R
H4b H -0.1789(13) 0.5795(4) 0.0119(4) 0.049(2) Uiso 1.000000 R
C2 C -0.4871(13) 0.7724(4) 0.0252(4) 0.0323(17) Uani 1.000000 .
H2a H -0.3886(14) 0.8133(11) 0.045(2) 0.048(2) Uiso 1.000000 GR
H2b H -0.598(6) 0.7882(18) -0.0165(7) 0.048(2) Uiso 1.000000 GR
H2c H -0.580(6) 0.7537(8) 0.0622(18) 0.048(2) Uiso 1.000000 GR
C3 C -0.4682(11) 0.6470(4) -0.0148(4) 0.0302(15) Uani 1.000000 .
H3a H -0.5618(11) 0.6354(4) 0.0253(4) 0.0363(18) Uiso 1.000000 R
H3b H -0.5853(11) 0.6554(4) -0.0581(4) 0.0363(18) Uiso 1.000000 R
C5 C -0.4582(14) 0.5126(4) -0.0340(4) 0.0391(18) Uani 1.000000 .
H5a H -0.6015(14) 0.5192(4) -0.0703(4) 0.047(2) Uiso 1.000000 R
H5b H -0.3565(14) 0.4745(4) -0.0518(4) 0.047(2) Uiso 1.000000 R
C1 C -0.1944(14) 0.7407(5) -0.0552(4) 0.0411(18) Uani 1.000000 .
H1a H -0.3089(19) 0.749(3) -0.0984(9) 0.062(3) Uiso 1.000000 GR
H1b H -0.110(8) 0.7856(16) -0.0404(12) 0.062(3) Uiso 1.000000 GR
H1c H -0.076(7) 0.7042(13) -0.066(2) 0.062(3) Uiso 1.000000 GR


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 Cl4 2.7608(16) . ?
Bi1 Cl3 2.5976(16) . ?
Bi1 Cl1 2.8056(15) . ?
Bi1 Cl2 2.6054(16) . ?
Bi1 Cl5 2.5472(18) . ?
N2 C8 1.497(8) . ?
N2 C6 1.493(7) . ?
N2 C7 1.477(8) . ?
C8 C9 1.511(9) . ?
C9 C10 1.511(9) . ?
C10 C10 1.508(13) 3_666 ?
N1 C2 1.482(8) . ?
N1 C3 1.502(8) . ?
N1 C1 1.472(8) . ?
C4 C3 1.500(9) . ?
C4 C5 1.542(10) . ?
C5 C5 1.487(14) 3_465 ?

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
Cl3 Bi1 Cl4 90.66(5) . . ?
Cl1 Bi1 Cl4 87.33(5) . . ?
Cl1 Bi1 Cl3 177.73(5) . . ?
Cl2 Bi1 Cl4 175.47(5) . . ?
Cl2 Bi1 Cl3 93.84(5) . . ?
Cl2 Bi1 Cl1 88.18(5) . . ?
Cl5 Bi1 Cl4 87.82(6) . . ?
Cl5 Bi1 Cl3 90.46(6) . . ?
Cl5 Bi1 Cl1 90.53(5) . . ?
Cl5 Bi1 Cl2 91.59(6) . . ?
C6 N2 C8 110.9(4) . . ?
C7 N2 C8 114.1(5) . . ?
C7 N2 C6 110.4(5) . . ?
C9 C8 N2 112.5(5) . . ?
C10 C9 C8 111.8(6) . . ?
C10 C10 C9 112.9(8) 3_666 . ?
C3 N1 C2 110.5(5) . . ?
C1 N1 C2 110.4(5) . . ?
C1 N1 C3 113.8(6) . . ?
C5 C4 C3 111.9(6) . . ?
C4 C3 N1 113.5(5) . . ?
C5 C5 C4 115.1(8) 3_465 . ?

_olex2_submission_special_instructions 'No special instructions were received'
