# Supplementary Information (SI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_apbii_auto
_database_code_depnum_ccdc_archive 'CCDC 2401299'
loop_
_audit_author_name
_audit_author_address
ap
;Fujian Normal University
China
;
_audit_update_record             
;
2024-11-08 deposited with the CCDC.	2025-11-21 downloaded from the CCDC.
;
_audit_creation_date             2024-11-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'Bi I6, I, 2(C6 H9 N3)'
_chemical_formula_sum            'C12 H18 Bi I7 N6'
_chemical_formula_weight         1343.60
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N Bi I'
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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
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'

_cell_length_a                   14.2687(6)
_cell_length_b                   14.3448(4)
_cell_length_c                   15.7364(7)
_cell_angle_alpha                90
_cell_angle_beta                 113.872(5)
_cell_angle_gamma                90
_cell_volume                     2945.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13131
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      31.1040
_cell_measurement_theta_min      2.1150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    13.333
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'dull dark black'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    3.030
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2344
_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  0.0429
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16646
_diffrn_reflns_point_group_measured_fraction_full 0.859
_diffrn_reflns_point_group_measured_fraction_max 0.667
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.818
_diffrn_reflns_theta_min         2.110
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     46.00  71.00   0.50    0.23    --   13.93 178.00   0.00   50
  2  ω    -16.00  17.00   0.50    0.23    --  -13.15 -83.00 110.00   66
  3  ω     49.00  89.00   0.50    0.23    --   13.93-178.00  60.00   80
  4  ω    -38.00  45.00   0.50    0.23    --   13.93 -83.00 110.00  166
  5  ω    -24.00  67.00   0.50    0.23    --  -13.15  19.00   0.00  182
  6  ω    -44.00  41.00   0.50    0.23    --  -13.15  83.00-128.00  170
  7  ω    -91.00 -66.00   0.50    0.23    --  -13.15-178.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0183131000
_diffrn_orient_matrix_UB_12      -0.0427012000
_diffrn_orient_matrix_UB_13      0.0236533000
_diffrn_orient_matrix_UB_21      -0.0301442000
_diffrn_orient_matrix_UB_22      0.0069863000
_diffrn_orient_matrix_UB_23      0.0258953000
_diffrn_orient_matrix_UB_31      -0.0413802000
_diffrn_orient_matrix_UB_32      -0.0239486000
_diffrn_orient_matrix_UB_33      -0.0346117000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.589
_reflns_Friedel_fraction_full    0.718
_reflns_Friedel_fraction_max     0.495
_reflns_number_gt                6018
_reflns_number_total             6710
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         3.190
_refine_diff_density_min         -1.852
_refine_diff_density_rms         0.243
_refine_ls_abs_structure_details 
;
 Flack x determined using 2121 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(5)
_refine_ls_extinction_coef       0.00022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         6710
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.038
_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)+(0.0674P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1094
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N4(H4), C5(H5), C8(H8), N1(H1A), C3(H3), C2(H2), C11(H11), C1(H1), C10(H10),
 C7(H7)
2.b X=CH2 refined with riding coordinates:
 N6(H6A,H6B), N3(H3A,H3B), N5(H5A,H5B), N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.44266(3) 0.62233(3) 0.44093(3) 0.02736(12) Uani 1 1 d . . . . .
I1 I 0.55506(7) 0.61547(6) 0.65646(7) 0.0355(2) Uani 1 1 d . . . . .
I5 I 0.31668(7) 0.45416(6) 0.45798(8) 0.0397(2) Uani 1 1 d . . . . .
I6 I 0.25990(8) 0.75262(7) 0.43069(8) 0.0415(2) Uani 1 1 d . . . . .
I3 I 0.59608(8) 0.48950(7) 0.41910(7) 0.0402(2) Uani 1 1 d . . . . .
I4 I 0.33828(8) 0.63728(7) 0.22652(7) 0.0408(2) Uani 1 1 d . . . . .
I2 I 0.58487(8) 0.79091(6) 0.46171(8) 0.0433(3) Uani 1 1 d . . . . .
I7 I -0.09117(13) 0.58911(12) 0.44704(13) 0.0763(4) Uani 1 1 d . . . . .
N6 N 0.8385(11) 0.5970(12) 0.7723(12) 0.059(4) Uani 1 1 d . . . . .
H6A H 0.7944 0.6372 0.7737 0.070 Uiso 1 1 calc R U . . .
H6B H 0.8748 0.5663 0.8217 0.070 Uiso 1 1 calc R U . . .
C4 C 0.9245(10) 0.5059(9) 0.6985(10) 0.031(3) Uani 1 1 d . . . . .
N4 N 1.0563(13) 0.3738(12) 0.6987(15) 0.070(6) Uani 1 1 d . . . . .
H4 H 1.0980 0.3302 0.6994 0.083 Uiso 1 1 calc R U . . .
N3 N 0.3290(12) 0.6168(12) 0.7000(15) 0.067(5) Uani 1 1 d . . . . .
H3A H 0.3584 0.5694 0.6879 0.080 Uiso 1 1 calc R U . . .
H3B H 0.3645 0.6560 0.7421 0.080 Uiso 1 1 calc R U . . .
N5 N 0.8014(13) 0.6236(11) 0.6222(11) 0.059(4) Uani 1 1 d . . . . .
H5A H 0.7561 0.6647 0.6184 0.070 Uiso 1 1 calc R U . . .
H5B H 0.8133 0.6105 0.5741 0.070 Uiso 1 1 calc R U . . .
C5 C 0.8947(12) 0.4399(10) 0.6321(11) 0.039(3) Uani 1 1 d . . . . .
H5 H 0.8281 0.4390 0.5867 0.047 Uiso 1 1 calc R U . . .
C8 C 0.119(2) 0.7657(14) 0.6037(15) 0.070(6) Uani 1 1 d . . . . .
H8 H 0.1022 0.7467 0.5428 0.084 Uiso 1 1 calc R U . . .
C9 C 0.1829(15) 0.7147(12) 0.6724(14) 0.050(4) Uani 1 1 d . . . . .
N1 N 0.1001(19) 0.8639(12) 0.7126(18) 0.080(6) Uani 1 1 d . . . . .
H1A H 0.0722 0.9117 0.7260 0.096 Uiso 1 1 calc R U . . .
C12 C 0.2324(18) 0.6290(14) 0.6554(17) 0.067(6) Uani 1 1 d . . . . .
N2 N 0.1771(19) 0.5686(14) 0.5903(15) 0.092(7) Uani 1 1 d . . . . .
H2A H 0.2062 0.5211 0.5780 0.111 Uiso 1 1 calc R U . . .
H2B H 0.1123 0.5771 0.5606 0.111 Uiso 1 1 calc R U . . .
C3 C 1.0237(12) 0.5050(12) 0.7684(14) 0.049(4) Uani 1 1 d . . . . .
H3 H 1.0444 0.5495 0.8154 0.058 Uiso 1 1 calc R U . . .
C6 C 0.8500(13) 0.5830(10) 0.6971(13) 0.046(4) Uani 1 1 d . . . . .
C2 C 1.0903(13) 0.4362(14) 0.7656(14) 0.061(6) Uani 1 1 d . . . . .
H2 H 1.1575 0.4341 0.8099 0.073 Uiso 1 1 calc R U . . .
C11 C 0.158(2) 0.8167(17) 0.7790(18) 0.078(7) Uani 1 1 d . . . . .
H11 H 0.1694 0.8338 0.8394 0.093 Uiso 1 1 calc R U . . .
C1 C 0.9666(17) 0.3719(12) 0.6325(15) 0.060(5) Uani 1 1 d . . . . .
H1 H 0.9493 0.3271 0.5860 0.072 Uiso 1 1 calc R U . . .
C10 C 0.206(2) 0.7397(16) 0.7642(16) 0.076(7) Uani 1 1 d . . . . .
H10 H 0.2529 0.7055 0.8135 0.091 Uiso 1 1 calc R U . . .
C7 C 0.075(2) 0.8480(14) 0.6202(18) 0.077(7) Uani 1 1 d . . . . .
H7 H 0.0341 0.8876 0.5731 0.092 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 3.1116(10) . ?
Bi1 I5 3.0843(10) . ?
Bi1 I6 3.1590(10) . ?
Bi1 I3 3.0249(10) . ?
Bi1 I4 3.0953(11) . ?
Bi1 I2 3.0879(10) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N6 C6 1.28(2) . ?
C4 C5 1.346(19) . ?
C4 C3 1.40(2) . ?
C4 C6 1.528(19) . ?
N4 H4 0.8600 . ?
N4 C2 1.32(2) . ?
N4 C1 1.28(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C12 1.28(3) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N5 C6 1.24(2) . ?
C5 H5 0.9300 . ?
C5 C1 1.41(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.32(3) . ?
C8 C7 1.41(3) . ?
C9 C12 1.50(2) . ?
C9 C10 1.39(3) . ?
N1 H1A 0.8600 . ?
N1 C11 1.24(3) . ?
N1 C7 1.37(3) . ?
C12 N2 1.33(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C3 H3 0.9300 . ?
C3 C2 1.38(2) . ?
C2 H2 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.37(3) . ?
C1 H1 0.9300 . ?
C10 H10 0.9300 . ?
C7 H7 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
I1 Bi1 I6 97.18(3) . . ?
I5 Bi1 I1 86.67(3) . . ?
I5 Bi1 I6 88.23(3) . . ?
I5 Bi1 I4 96.24(3) . . ?
I5 Bi1 I2 169.88(4) . . ?
I3 Bi1 I1 91.51(3) . . ?
I3 Bi1 I5 89.50(3) . . ?
I3 Bi1 I6 170.87(4) . . ?
I3 Bi1 I4 88.33(3) . . ?
I3 Bi1 I2 91.75(3) . . ?
I4 Bi1 I1 177.08(3) . . ?
I4 Bi1 I6 83.12(3) . . ?
I2 Bi1 I1 83.26(3) . . ?
I2 Bi1 I6 92.04(3) . . ?
I2 Bi1 I4 93.83(3) . . ?
H6A N6 H6B 120.0 . . ?
C6 N6 H6A 120.0 . . ?
C6 N6 H6B 120.0 . . ?
C5 C4 C3 120.4(13) . . ?
C5 C4 C6 119.9(12) . . ?
C3 C4 C6 119.7(12) . . ?
C2 N4 H4 117.0 . . ?
C1 N4 H4 117.0 . . ?
C1 N4 C2 126.0(15) . . ?
H3A N3 H3B 120.0 . . ?
C12 N3 H3A 120.0 . . ?
C12 N3 H3B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C6 N5 H5A 120.0 . . ?
C6 N5 H5B 120.0 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C1 118.8(15) . . ?
C1 C5 H5 120.6 . . ?
C9 C8 H8 119.1 . . ?
C9 C8 C7 122(2) . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C12 122.0(19) . . ?
C8 C9 C10 120.3(19) . . ?
C10 C9 C12 117.7(19) . . ?
C11 N1 H1A 116.6 . . ?
C11 N1 C7 126.9(19) . . ?
C7 N1 H1A 116.6 . . ?
N3 C12 C9 120(2) . . ?
N3 C12 N2 120(2) . . ?
N2 C12 C9 120(2) . . ?
C12 N2 H2A 120.0 . . ?
C12 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C4 C3 H3 120.9 . . ?
C2 C3 C4 118.2(15) . . ?
C2 C3 H3 120.9 . . ?
N6 C6 C4 116.8(16) . . ?
N5 C6 N6 125.1(17) . . ?
N5 C6 C4 118.0(16) . . ?
N4 C2 C3 118.4(16) . . ?
N4 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
N1 C11 H11 119.7 . . ?
N1 C11 C10 121(2) . . ?
C10 C11 H11 119.7 . . ?
N4 C1 C5 118.3(16) . . ?
N4 C1 H1 120.9 . . ?
C5 C1 H1 120.9 . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117(2) . . ?
C11 C10 H10 121.4 . . ?
C8 C7 H7 123.5 . . ?
N1 C7 C8 113.1(17) . . ?
N1 C7 H7 123.5 . . ?

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
C4 C5 C1 N4 3(3) . . . . ?
C4 C3 C2 N4 -2(3) . . . . ?
C5 C4 C3 C2 2(3) . . . . ?
C5 C4 C6 N6 129.2(17) . . . . ?
C5 C4 C6 N5 -47(2) . . . . ?
C8 C9 C12 N3 132(3) . . . . ?
C8 C9 C12 N2 -44(3) . . . . ?
C8 C9 C10 C11 2(4) . . . . ?
C9 C8 C7 N1 -5(4) . . . . ?
N1 C11 C10 C9 -3(4) . . . . ?
C12 C9 C10 C11 -178(2) . . . . ?
C3 C4 C5 C1 -2(3) . . . . ?
C3 C4 C6 N6 -52(2) . . . . ?
C3 C4 C6 N5 132.2(19) . . . . ?
C6 C4 C5 C1 177.1(17) . . . . ?
C6 C4 C3 C2 -177.7(19) . . . . ?
C2 N4 C1 C5 -3(4) . . . . ?
C11 N1 C7 C8 4(4) . . . . ?
C1 N4 C2 C3 2(4) . . . . ?
C10 C9 C12 N3 -48(3) . . . . ?
C10 C9 C12 N2 136(3) . . . . ?
C7 C8 C9 C12 -178(2) . . . . ?
C7 C8 C9 C10 2(4) . . . . ?
C7 N1 C11 C10 0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.077
_oxdiff_exptl_absorpt_empirical_full_min 0.508
