# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_B
_database_code_depnum_ccdc_archive 'CCDC 2183662'
loop_
_audit_author_name
_audit_author_address
'Bo Zhang'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2023-01-14 deposited with the CCDC.	2023-01-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H36 Bi2 Cu2 I12 N4'
_chemical_formula_weight         2352.33

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_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                   28.132(3)
_cell_length_b                   9.2296(9)
_cell_length_c                   16.8237(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.638(2)
_cell_angle_gamma                90
_cell_volume                     4353.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3886
_cell_measurement_theta_min      2.323
_cell_measurement_theta_max      28.3075

_exptl_crystal_description       sheet
_exptl_crystal_colour            dark-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.589
_exptl_crystal_F_000             4080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    17.548
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9841
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.323
_diffrn_reflns_theta_max         25.017
_diffrn_reflns_theta_full        25.017
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3801
_reflns_number_gt                2843
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1019P)²+79.4173P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00091(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3801
_refine_ls_number_parameters     166
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1825
_refine_ls_wR_factor_gt          0.1689
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
Bi1 Bi 0.36853(3) 0.97819(8) 0.12137(5) 0.0296(3) Uani 1 1 d . . . . .
I1 I 0.42664(4) 0.95059(14) 0.29958(8) 0.0319(4) Uani 1 1 d . . . . .
I2 I 0.31118(6) 1.22028(18) 0.17598(11) 0.0514(5) Uani 1 1 d . . . . .
I3 I 0.29467(5) 0.76069(17) 0.15349(10) 0.0452(5) Uani 1 1 d . . . . .
I4 I 0.45691(5) 1.17527(18) 0.08685(12) 0.0607(6) Uani 1 1 d . . . . .
I5 I 0.44434(5) 0.71488(15) 0.09739(9) 0.0383(4) Uani 1 1 d . . . . .
I6 I 0.32694(5) 1.00974(13) -0.04300(9) 0.0342(4) Uani 1 1 d . . . . .
Cu1 Cu 0.51765(11) 0.9452(4) 0.3237(2) 0.0668(10) Uani 1 1 d . . . . .
N1 N 0.3364(6) 0.4769(15) 0.9250(10) 0.026(4) Uani 1 1 d . . . . .
N2 N 0.4064(5) 0.5283(17) 0.8467(10) 0.028(4) Uani 1 1 d . . . . .
C1 C 0.2931(8) 0.448(2) 0.9699(13) 0.040(5) Uani 1 1 d . . . . .
H1A H 0.2957 0.5008 1.0192 0.061 Uiso 1 1 calc R U . . .
H1B H 0.2911 0.3460 0.9809 0.061 Uiso 1 1 calc R U . . .
H1C H 0.2650 0.4781 0.9382 0.061 Uiso 1 1 calc R U . . .
C2 C 0.3446(7) 0.6323(18) 0.9170(13) 0.033(5) Uani 1 1 d . . . . .
H2A H 0.3485 0.6755 0.9696 0.039 Uiso 1 1 calc R U . . .
H2B H 0.3167 0.6759 0.8887 0.039 Uiso 1 1 calc R U . . .
C3 C 0.3811(7) 0.4088(19) 0.9651(12) 0.031(5) Uani 1 1 d . . . . .
H3A H 0.3761 0.3054 0.9708 0.037 Uiso 1 1 calc R U . . .
H3B H 0.3875 0.4497 1.0180 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3266(7) 0.415(2) 0.8417(11) 0.033(5) Uani 1 1 d . . . . .
H4A H 0.2977 0.4563 0.8161 0.040 Uiso 1 1 calc R U . . .
H4B H 0.3226 0.3105 0.8445 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3693(7) 0.451(2) 0.7938(13) 0.035(5) Uani 1 1 d . . . . .
H5A H 0.3826 0.3631 0.7734 0.042 Uiso 1 1 calc R U . . .
H5B H 0.3590 0.5126 0.7488 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3868(7) 0.666(2) 0.8739(12) 0.033(5) Uani 1 1 d . U . . .
H6A H 0.3780 0.7278 0.8286 0.040 Uiso 1 1 calc R U . . .
H6B H 0.4105 0.7158 0.9090 0.040 Uiso 1 1 calc R U . . .
C7 C 0.4243(6) 0.435(2) 0.9160(12) 0.031(5) Uani 1 1 d . . . . .
H7A H 0.4496 0.4843 0.9482 0.038 Uiso 1 1 calc R U . . .
H7B H 0.4366 0.3442 0.8975 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4489(9) 0.553(4) 0.7985(19) 0.079(10) Uani 1 1 d . . . . .
H8A H 0.4742 0.5977 0.8317 0.118 Uiso 1 1 calc R U . . .
H8B H 0.4398 0.6157 0.7543 0.118 Uiso 1 1 calc R U . . .
H8C H 0.4597 0.4622 0.7791 0.118 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
Bi1 I6 2.9288(16) . ?
Bi1 I2 2.9460(16) . ?
Bi1 I3 2.9698(15) . ?
Bi1 I4 3.1721(16) . ?
Bi1 Cu1 3.274(3) 2_655 ?
Bi1 I5 3.2798(16) . ?
Bi1 I1 3.3066(16) . ?
I1 Cu1 2.560(3) . ?
I1 Cu1 2.700(4) 2_655 ?
I4 Cu1 2.666(4) 2_655 ?
I5 Cu1 2.682(4) 2_655 ?
Cu1 Cu1 2.597(8) 2_655 ?
Cu1 I4 2.666(4) 2_655 ?
Cu1 I5 2.682(4) 2_655 ?
Cu1 I1 2.700(4) 2_655 ?
Cu1 Bi1 3.274(3) 2_655 ?
N1 C2 1.46(2) . ?
N1 C1 1.51(3) . ?
N1 C3 1.51(2) . ?
N1 C4 1.52(2) . ?
N2 C6 1.47(2) . ?
N2 C5 1.50(2) . ?
N2 C7 1.50(2) . ?
N2 C8 1.51(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C6 1.47(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C7 1.54(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.54(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
I6 Bi1 I2 91.83(5) . . ?
I6 Bi1 I3 90.41(4) . . ?
I2 Bi1 I3 92.70(5) . . ?
I6 Bi1 I4 91.68(5) . . ?
I2 Bi1 I4 94.55(5) . . ?
I3 Bi1 I4 172.39(5) . . ?
I6 Bi1 Cu1 125.62(8) . 2_655 ?
I2 Bi1 Cu1 122.02(8) . 2_655 ?
I3 Bi1 Cu1 124.65(7) . 2_655 ?
I4 Bi1 Cu1 48.83(7) . 2_655 ?
I6 Bi1 I5 99.88(4) . . ?
I2 Bi1 I5 168.05(5) . . ?
I3 Bi1 I5 89.60(4) . . ?
I4 Bi1 I5 82.83(4) . . ?
Cu1 Bi1 I5 48.32(7) 2_655 . ?
I6 Bi1 I1 173.85(4) . . ?
I2 Bi1 I1 91.08(4) . . ?
I3 Bi1 I1 94.87(4) . . ?
I4 Bi1 I1 82.69(4) . . ?
Cu1 Bi1 I1 48.44(7) 2_655 . ?
I5 Bi1 I1 77.04(4) . . ?
Cu1 I1 Cu1 59.10(15) . 2_655 ?
Cu1 I1 Bi1 124.07(10) . . ?
Cu1 I1 Bi1 65.15(8) 2_655 . ?
Cu1 I4 Bi1 67.59(8) 2_655 . ?
Cu1 I5 Bi1 65.73(8) 2_655 . ?
I1 Cu1 Cu1 63.13(13) . 2_655 ?
I1 Cu1 I4 107.08(13) . 2_655 ?
Cu1 Cu1 I4 127.12(9) 2_655 2_655 ?
I1 Cu1 I5 116.58(14) . 2_655 ?
Cu1 Cu1 I5 125.37(10) 2_655 2_655 ?
I4 Cu1 I5 105.91(14) 2_655 2_655 ?
I1 Cu1 I1 120.85(15) . 2_655 ?
Cu1 Cu1 I1 57.76(14) 2_655 2_655 ?
I4 Cu1 I1 105.84(13) 2_655 2_655 ?
I5 Cu1 I1 99.30(12) 2_655 2_655 ?
I1 Cu1 Bi1 170.29(16) . 2_655 ?
Cu1 Cu1 Bi1 124.0(2) 2_655 2_655 ?
I4 Cu1 Bi1 63.59(8) 2_655 2_655 ?
I5 Cu1 Bi1 65.95(8) 2_655 2_655 ?
I1 Cu1 Bi1 66.41(8) 2_655 2_655 ?
C2 N1 C1 111.1(15) . . ?
C2 N1 C3 108.6(14) . . ?
C1 N1 C3 112.2(16) . . ?
C2 N1 C4 107.7(15) . . ?
C1 N1 C4 107.5(14) . . ?
C3 N1 C4 109.6(15) . . ?
C6 N2 C5 109.5(15) . . ?
C6 N2 C7 111.2(16) . . ?
C5 N2 C7 111.4(15) . . ?
C6 N2 C8 111.6(18) . . ?
C5 N2 C8 107.3(18) . . ?
C7 N2 C8 105.8(17) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C6 113.0(16) . . ?
N1 C2 H2A 109.0 . . ?
C6 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C6 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C7 111.0(16) . . ?
N1 C3 H3A 109.4 . . ?
C7 C3 H3A 109.4 . . ?
N1 C3 H3B 109.4 . . ?
C7 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C5 108.0(15) . . ?
N1 C4 H4A 110.1 . . ?
C5 C4 H4A 110.1 . . ?
N1 C4 H4B 110.1 . . ?
C5 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
N2 C5 C4 109.3(16) . . ?
N2 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
N2 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N2 C6 C2 108.1(15) . . ?
N2 C6 H6A 110.1 . . ?
C2 C6 H6A 110.1 . . ?
N2 C6 H6B 110.1 . . ?
C2 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
N2 C7 C3 106.0(14) . . ?
N2 C7 H7A 110.5 . . ?
C3 C7 H7A 110.5 . . ?
N2 C7 H7B 110.5 . . ?
C3 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
C1 H1A I3 0.96 3.30 4.23(2) 163.3 1_556
C1 H1B I6 0.96 3.30 4.16(2) 150.9 1_546
C1 H1C I2 0.96 3.31 3.98(2) 128.8 7_566
C1 H1C I3 0.96 3.25 4.10(2) 148.2 7_566
C1 H1C I6 0.96 3.25 3.71(2) 111.5 7_566
C2 H2A I5 0.97 3.33 4.04(2) 131.4 1_556
C2 H2B I3 0.97 3.21 4.120(19) 156.9 7_566
C3 H3A I6 0.97 3.06 3.984(18) 159.5 1_546
C3 H3B I5 0.97 3.16 3.93(2) 137.6 1_556
C5 H5A I1 0.97 3.17 4.04(2) 151.2 6_566
C5 H5B I2 0.97 3.02 3.91(2) 152.6 6_576
C6 H6A I1 0.97 3.32 3.948(19) 124.1 6_576
C6 H6A I2 0.97 3.09 3.95(2) 147.5 6_576
C6 H6B I5 0.97 3.24 4.00(2) 136.6 1_556
C7 H7A I5 0.97 3.30 4.00(2) 130.4 1_556
C7 H7B I1 0.97 3.18 4.07(2) 152.8 6_566
C8 H8A I4 0.96 3.10 4.02(3) 162.5 5_676

_refine_diff_density_max         4.960
_refine_diff_density_min         -2.158
_refine_diff_density_rms         0.450


# start Validation Reply Form
_vrf_PLAT342_B                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03 Ang.  
RESPONSE:This is due to the relatively weak diffraction of crystal which 
resulted in relatively low ratio of observed reflections and parametes.
;
# end Validation Reply Form
