# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2206021'
loop_
_audit_author_name
_audit_author_address
'Yuyin Wang'
;Jining University
China
;
_audit_update_record             
;
2023-03-07 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_audit_creation_date             2022-09-08
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'Bi I6, 2(I1.5), 2(C5 H16 N2)'
_chemical_formula_sum            'C10 H32 Bi I9 N4'
_chemical_formula_weight         1559.47
_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'
I I -0.4742 1.8119 '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      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, 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'
'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, y, z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.8846(9)
_cell_length_b                   11.8525(8)
_cell_length_c                   23.9410(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3372.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9139
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.19
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    13.472
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    3.072
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       black
_exptl_crystal_F_000             2720
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26136
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_min         2.427
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1738
_reflns_number_total             2246
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         3.529
_refine_diff_density_min         -1.921
_refine_diff_density_rms         0.318
_refine_ls_extinction_coef       0.00275(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         2246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.093
_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)+(0.0451P)²+99.0014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1345
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C1(H1D,H1E)
2.b Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.0000 0.0000 0.5000 0.0394(3) Uani 1 4 d S T P . .
I1 I 0.25667(8) 0.0000 0.5000 0.0529(3) Uani 1 2 d S T P . .
I3 I 0.0000 -0.25571(8) 0.48538(4) 0.0449(3) Uani 1 2 d S T P . .
I2 I 0.0000 0.03873(11) 0.37227(5) 0.0657(4) Uani 1 2 d S T P . .
I5 I 0.0000 0.46917(16) 0.2500 0.0689(5) Uani 1 4 d S T P . .
I4 I 0.0000 0.46894(16) 0.37162(6) 0.0982(6) Uani 1 2 d S T P . .
N1 N 0.2341(10) 0.2478(9) 0.0964(5) 0.071(3) Uani 1 1 d . . . . .
H1A H 0.1620 0.2336 0.1037 0.107 Uiso 1 1 calc R U . . .
H1B H 0.2639 0.1896 0.0782 0.107 Uiso 1 1 calc R U . . .
H1C H 0.2393 0.3096 0.0754 0.107 Uiso 1 1 calc R U . . .
C2 C 0.2470(14) 0.2392(14) 0.1979(6) 0.086(5) Uani 1 1 d . . . . .
H2A H 0.2295 0.1593 0.1973 0.103 Uiso 1 1 calc R U . . .
H2B H 0.1759 0.2790 0.2000 0.103 Uiso 1 1 calc R U . . .
C3 C 0.307(3) 0.261(2) 0.2500 0.109(10) Uani 1 2 d S T P . .
H3A H 0.3753 0.2163 0.2500 0.131 Uiso 1 2 calc R U P . .
H3B H 0.3299 0.3400 0.2500 0.131 Uiso 1 2 calc R U P . .
C1 C 0.2939(17) 0.2650(18) 0.1481(6) 0.116(8) Uani 1 1 d . . . . .
H1D H 0.3635 0.2226 0.1454 0.139 Uiso 1 1 calc R U . . .
H1E H 0.3145 0.3442 0.1495 0.139 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 I1 3.0504(9) 9_556 ?
Bi1 I1 3.0504(9) . ?
Bi1 I3 3.0510(9) . ?
Bi1 I3 3.0509(9) 9_556 ?
Bi1 I2 3.0923(12) 9_556 ?
Bi1 I2 3.0922(12) . ?
I5 I4 2.9116(14) 10_556 ?
I5 I4 2.9116(14) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.44(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.46(2) . ?
C2 C1 1.35(2) . ?
C3 C2 1.46(2) 10_556 ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?

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
I1 Bi1 I1 180.0 9_556 . ?
I1 Bi1 I3 90.0 . 9_556 ?
I1 Bi1 I3 90.0 . . ?
I1 Bi1 I3 90.0 9_556 9_556 ?
I1 Bi1 I3 90.0 9_556 . ?
I1 Bi1 I2 90.0 9_556 . ?
I1 Bi1 I2 90.0 . 9_556 ?
I1 Bi1 I2 90.0 . . ?
I1 Bi1 I2 90.0 9_556 9_556 ?
I3 Bi1 I3 180.0 9_556 . ?
I3 Bi1 I2 88.05(3) . 9_556 ?
I3 Bi1 I2 91.95(3) . . ?
I3 Bi1 I2 88.05(3) 9_556 . ?
I3 Bi1 I2 91.95(3) 9_556 9_556 ?
I2 Bi1 I2 180.0 . 9_556 ?
I4 I5 I4 179.90(11) 10_556 . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H2A C2 H2B 106.8 . . ?
C3 C2 H2A 107.1 . . ?
C3 C2 H2B 107.1 . . ?
C1 C2 H2A 107.1 . . ?
C1 C2 H2B 107.1 . . ?
C1 C2 C3 120.7(18) . . ?
C2 C3 C2 117(3) 10_556 . ?
C2 C3 H3A 108.0 10_556 . ?
C2 C3 H3A 108.0 . . ?
C2 C3 H3B 108.0 10_556 . ?
C2 C3 H3B 108.0 . . ?
H3A C3 H3B 107.2 . . ?
N1 C1 H1D 107.0 . . ?
N1 C1 H1E 107.0 . . ?
C2 C1 N1 121.5(17) . . ?
C2 C1 H1D 107.0 . . ?
C2 C1 H1E 107.0 . . ?
H1D C1 H1E 106.7 . . ?

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 C2 C1 N1 -177.5(18) . . . . ?
C1 C2 C3 C2 175.3(16) . . . 10_556 ?


_olex2_submission_special_instructions 'No special instructions were received'
