# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_cmp1
_database_code_depnum_ccdc_archive 'CCDC 2336516'
loop_
_audit_author_name
_audit_author_address
'Guang-Ning Liu'
;University of Jinan
China
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2024-06-06 downloaded from the CCDC.
;
_audit_creation_date             2023-11-23
_chemical_oxdiff_formula         'Bi I C H N'
_diffrn_orient_matrix_UB_11      0.0815240000
_diffrn_orient_matrix_UB_12      0.0145442000
_diffrn_orient_matrix_UB_13      0.0179084000
_diffrn_orient_matrix_UB_21      0.0454125000
_diffrn_orient_matrix_UB_22      -0.0350451000
_diffrn_orient_matrix_UB_23      -0.0415464000
_diffrn_orient_matrix_UB_31      -0.0043490000
_diffrn_orient_matrix_UB_32      0.0643059000
_diffrn_orient_matrix_UB_33      -0.0459016000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_audit_creation_method           
;
FinalCif V106 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C7 H9 Bi I4 N2 O'
_chemical_formula_moiety         'Bi I4, C7 H7 N2, H2 O'
_chemical_formula_weight         853.74
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H1B-H1B_$1
 2.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4.a Free rotating group:
 O1(H1A,H1B)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7)
;
_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 1.861
_oxdiff_exptl_absorpt_empirical_full_min 0.638
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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'

_cell_length_a                   7.6459(3)
_cell_length_b                   9.8910(4)
_cell_length_c                   11.4115(5)
_cell_angle_alpha                74.820(4)
_cell_angle_beta                 86.247(3)
_cell_angle_gamma                83.582(3)
_cell_volume                     827.08(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3917
_cell_measurement_theta_min      3.7140
_cell_measurement_theta_max      28.8660
_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light red'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.428
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    18.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40915
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.122
_shelx_estimated_absorpt_T_max   0.220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_environment      ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0355
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  43.00   1.00   15.31    --   16.17 -77.00 120.00   94
  2  ω    -11.00  84.00   1.00   15.31    --   16.17  77.00-120.00   95
  3  ω    -51.00  33.00   1.00   15.31    --   16.17 -57.00   0.00   84
  4  ω    -25.00  22.00   1.00   15.31    --  -16.64 -99.00   0.00   47
  5  ω    -25.00  22.00   1.00   15.31    --  -16.64 -99.00 -90.00   47
  6  ω     -3.00  85.00   1.00   15.31    --   16.17  37.00 150.00   88
  7  ω     -3.00  85.00   1.00   15.31    --   16.17  37.00  60.00   88
  8  ω     32.00  89.00   1.00   15.31    --   16.17-178.00 -30.00   57
;
_diffrn_reflns_number            9503
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_theta_min         3.172
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3075
_reflns_number_gt                2756
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0232P)²+0.6791P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3075
_refine_ls_number_parameters     140
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0584
_refine_ls_wR_factor_gt          0.0554
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.107
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00041(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_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 0.26926(3) 0.92583(2) 0.41550(2) 0.03250(10) Uani 1 1 d . . . . .
I1 I 0.60948(5) 0.77618(4) 0.54082(5) 0.04236(13) Uani 1 1 d . . . . .
I2 I 0.15766(7) 0.65390(5) 0.41874(5) 0.05826(16) Uani 1 1 d . . . . .
I3 I 0.42502(7) 0.97696(5) 0.16916(5) 0.05398(15) Uani 1 1 d . . . . .
I4 I -0.07475(6) 1.10132(5) 0.31642(4) 0.04569(13) Uani 1 1 d . . . . .
N1 N 0.3432(10) 0.5379(9) 0.7680(9) 0.087(2) Uani 1 1 d . U . . .
H1 H 0.3884 0.6022 0.7120 0.104 Uiso 1 1 calc R . . . .
N2 N 0.2343(10) 0.3455(8) 0.8565(8) 0.077(2) Uani 1 1 d . . . . .
H2 H 0.1970 0.2641 0.8674 0.093 Uiso 1 1 calc R . . . .
C1 C 0.3073(9) 0.5446(8) 0.8865(8) 0.054(2) Uani 1 1 d . . . . .
C2 C 0.3237(11) 0.6421(9) 0.9486(11) 0.072(3) Uani 1 1 d . U . . .
H2A H 0.3681 0.7270 0.9101 0.086 Uiso 1 1 calc R . . . .
C3 C 0.2749(12) 0.6132(10) 1.0653(12) 0.084(3) Uani 1 1 d . . . . .
H3 H 0.2864 0.6781 1.1097 0.101 Uiso 1 1 calc R . . . .
C4 C 0.2055(11) 0.4848(10) 1.1231(9) 0.069(2) Uani 1 1 d . . . . .
H4 H 0.1719 0.4669 1.2051 0.083 Uiso 1 1 calc R . . . .
C5 C 0.1871(9) 0.3894(8) 1.0635(8) 0.053(2) Uani 1 1 d . . . . .
H5 H 0.1418 0.3048 1.1020 0.064 Uiso 1 1 calc R . . . .
C6 C 0.2373(9) 0.4203(7) 0.9435(7) 0.0470(18) Uani 1 1 d . . . . .
C7 C 0.2996(13) 0.4228(12) 0.7536(10) 0.090(3) Uani 1 1 d . U . . .
H7 H 0.3121 0.3967 0.6807 0.108 Uiso 1 1 calc R . . . .
O1 O 0.0760(12) 0.1016(9) 0.8986(12) 0.142(3) Uani 1 1 d . . . . .
H1A H 0.0813 0.0248 0.8776 0.213 Uiso 1 1 d G . . . .
H1B H -0.0220 0.1054 0.9378 0.213 Uiso 1 1 d DG . . . .


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 3.0855(5) . ?
Bi1 I1 3.3521(5) 2_676 ?
Bi1 I2 2.9018(5) . ?
Bi1 I3 2.9204(6) . ?
Bi1 I4 3.2720(5) 2_576 ?
Bi1 I4 3.0904(5) . ?
I1 Bi1 3.3521(5) 2_676 ?
I4 Bi1 3.2720(5) 2_576 ?
N1 H1 0.8600 . ?
N1 C1 1.379(11) . ?
N1 C7 1.275(13) . ?
N2 H2 0.8600 . ?
N2 C6 1.388(10) . ?
N2 C7 1.323(12) . ?
C1 C2 1.358(13) . ?
C1 C6 1.379(10) . ?
C2 H2A 0.9300 . ?
C2 C3 1.325(14) . ?
C3 H3 0.9300 . ?
C3 C4 1.412(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.323(11) . ?
C5 H5 0.9300 . ?
C5 C6 1.362(10) . ?
C7 H7 0.9300 . ?
O1 H1A 0.8505 . ?
O1 H1B 0.8493 . ?

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 86.966(12) . 2_676 ?
I1 Bi1 I4 89.053(14) . 2_576 ?
I1 Bi1 I4 171.842(15) . . ?
I2 Bi1 I1 171.037(17) . 2_676 ?
I2 Bi1 I1 89.498(15) . . ?
I2 Bi1 I3 95.023(17) . . ?
I2 Bi1 I4 96.215(16) . . ?
I2 Bi1 I4 88.520(16) . 2_576 ?
I3 Bi1 I1 95.151(16) . . ?
I3 Bi1 I1 93.496(15) . 2_676 ?
I3 Bi1 I4 174.517(14) . 2_576 ?
I3 Bi1 I4 90.159(15) . . ?
I4 Bi1 I1 86.531(13) . 2_676 ?
I4 Bi1 I1 83.193(14) 2_576 2_676 ?
I4 Bi1 I4 85.290(14) . 2_576 ?
Bi1 I1 Bi1 93.034(12) . 2_676 ?
Bi1 I4 Bi1 94.710(14) . 2_576 ?
C1 N1 H1 124.9 . . ?
C7 N1 H1 124.9 . . ?
C7 N1 C1 110.2(9) . . ?
C6 N2 H2 126.4 . . ?
C7 N2 H2 126.4 . . ?
C7 N2 C6 107.2(8) . . ?
N1 C1 C6 105.1(8) . . ?
C2 C1 N1 134.4(9) . . ?
C2 C1 C6 120.5(9) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 C1 118.4(9) . . ?
C3 C2 H2A 120.8 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(10) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.7(10) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 121.4 . . ?
C4 C5 C6 117.2(8) . . ?
C6 C5 H5 121.4 . . ?
C1 C6 N2 106.8(8) . . ?
C5 C6 N2 131.6(7) . . ?
C5 C6 C1 121.6(8) . . ?
N1 C7 N2 110.8(10) . . ?
N1 C7 H7 124.6 . . ?
N2 C7 H7 124.6 . . ?
H1A O1 H1B 104.5 . . ?


####################################################################### 
# 
# 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_cmp2
_database_code_depnum_ccdc_archive 'CCDC 2336517'
loop_
_audit_author_name
_audit_author_address
'Guang-Ning Liu'
;University of Jinan
China
;
_audit_update_record             
;
2024-02-29 deposited with the CCDC.	2024-06-06 downloaded from the CCDC.
;
_audit_creation_date             2023-11-23
_chemical_oxdiff_formula         'Bi I C H O N'
_diffrn_orient_matrix_UB_11      0.0454540000
_diffrn_orient_matrix_UB_12      -0.0506533000
_diffrn_orient_matrix_UB_13      -0.0357977000
_diffrn_orient_matrix_UB_21      -0.0134651000
_diffrn_orient_matrix_UB_22      0.0457531000
_diffrn_orient_matrix_UB_23      -0.0521036000
_diffrn_orient_matrix_UB_31      0.0872790000
_diffrn_orient_matrix_UB_32      0.0114377000
_diffrn_orient_matrix_UB_33      -0.0010480000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_audit_creation_method           
;
FinalCif V106 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C9 H11 Bi I4 N2'
_chemical_formula_moiety         'Bi I4, C9 H11 N2'
_chemical_formula_weight         863.78
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_chemical_melting_point          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C2(H2), C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C7(H7A,H7B,H7C)
;
_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 4.790
_oxdiff_exptl_absorpt_empirical_full_min 0.522
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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'

_cell_length_a                   7.6058(4)
_cell_length_b                   10.8679(5)
_cell_length_c                   11.5758(5)
_cell_angle_alpha                79.148(4)
_cell_angle_beta                 77.920(4)
_cell_angle_gamma                72.081(4)
_cell_volume                     882.34(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3088
_cell_measurement_theta_min      3.6370
_cell_measurement_theta_max      28.6910
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear light red'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_density_meas      ?
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.251
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    16.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.12182
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.026
_shelx_estimated_absorpt_T_max   0.630
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      293(2)
_diffrn_ambient_environment      ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_ambient_temperature_device_make ?
_diffrn_radiation_probe          x-ray
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0355
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  43.00   1.00    7.34    --   16.17 -77.00  30.00   94
  2  ω    -51.00  43.00   1.00    7.34    --   16.17 -77.00-120.00   94
  3  ω    -11.00  84.00   1.00    7.34    --   16.17  77.00 150.00   95
  4  ω    -25.00  22.00   1.00    7.34    --  -16.64 -99.00 -60.00   47
  5  ω    -33.00  51.00   1.00    7.34    --  -16.64  57.00 -60.00   84
  6  ω     -1.00  83.00   1.00    7.34    --   16.17  57.00  30.00   84
  7  ω     -1.00  24.00   1.00    7.34    --   16.17  57.00 -90.00   25
  8  ω    -53.00  35.00   1.00    7.34    --   16.17 -37.00  90.00   88
;
_diffrn_reflns_number            10152
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_theta_min         2.987
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3280
_reflns_number_gt                2774
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0243P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3280
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0654
_refine_ls_wR_factor_gt          0.0599
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.967
_refine_diff_density_min         -0.978
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

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'

_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_
_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 0.68881(3) 0.07182(3) 0.08777(2) 0.03700(11) Uani 1 1 d . . . . .
I1 I 1.05994(6) -0.08241(5) 0.18025(4) 0.04609(15) Uani 1 1 d . . . . .
I2 I 0.34090(7) 0.20592(5) -0.03189(5) 0.05103(16) Uani 1 1 d . . . . .
I3 I 0.48680(7) 0.02472(5) 0.32812(5) 0.05512(17) Uani 1 1 d . . . . .
I4 I 0.70056(7) 0.32976(5) 0.12005(5) 0.05487(17) Uani 1 1 d . . . . .
N1 N 0.9382(8) 0.2874(6) 0.4004(6) 0.0451(15) Uani 1 1 d . . . . .
N2 N 1.0053(8) 0.4490(6) 0.2743(6) 0.0434(15) Uani 1 1 d . . . . .
C6 C 0.8807(9) 0.5032(7) 0.3692(7) 0.0406(18) Uani 1 1 d . . . . .
C1 C 0.8407(9) 0.3999(7) 0.4501(7) 0.0426(19) Uani 1 1 d . . . . .
C5 C 0.8029(11) 0.6326(8) 0.3903(9) 0.058(2) Uani 1 1 d . . . . .
H5 H 0.8278 0.7019 0.3352 0.070 Uiso 1 1 calc R . . . .
C8 C 1.0337(10) 0.3222(8) 0.2966(7) 0.049(2) Uani 1 1 d . . . . .
H8 H 1.1116 0.2638 0.2456 0.059 Uiso 1 1 calc R . . . .
C2 C 0.7233(11) 0.4191(9) 0.5583(7) 0.059(2) Uani 1 1 d . . . . .
H2 H 0.6973 0.3499 0.6130 0.070 Uiso 1 1 calc R . . . .
C4 C 0.6880(12) 0.6510(10) 0.4968(10) 0.073(3) Uani 1 1 d . . . . .
H4 H 0.6342 0.7356 0.5154 0.088 Uiso 1 1 calc R . . . .
C9 C 0.9324(14) 0.1551(8) 0.4510(8) 0.077(3) Uani 1 1 d . . . . .
H9A H 0.9470 0.1403 0.5333 0.115 Uiso 1 1 calc GR . . . .
H9B H 1.0321 0.0937 0.4081 0.115 Uiso 1 1 calc GR . . . .
H9C H 0.8144 0.1440 0.4448 0.115 Uiso 1 1 calc GR . . . .
C3 C 0.6477(11) 0.5467(11) 0.5800(9) 0.074(3) Uani 1 1 d . . . . .
H3 H 0.5679 0.5644 0.6513 0.088 Uiso 1 1 calc R . . . .
C7 C 1.0885(11) 0.5199(8) 0.1670(7) 0.062(2) Uani 1 1 d . . . . .
H7A H 0.9920 0.5901 0.1348 0.093 Uiso 1 1 calc GR . . . .
H7B H 1.1495 0.4615 0.1087 0.093 Uiso 1 1 calc GR . . . .
H7C H 1.1784 0.5546 0.1870 0.093 Uiso 1 1 calc 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 I1 3.2879(6) 2_755 ?
Bi1 I1 3.0986(5) . ?
Bi1 I2 3.0734(6) . ?
Bi1 I2 3.2858(6) 2_655 ?
Bi1 I3 2.9193(6) . ?
Bi1 I4 2.9271(6) . ?
I1 Bi1 3.2879(6) 2_755 ?
I2 Bi1 3.2859(6) 2_655 ?
N1 C1 1.380(8) . ?
N1 C8 1.321(9) . ?
N1 C9 1.458(10) . ?
N2 C6 1.384(9) . ?
N2 C8 1.311(9) . ?
N2 C7 1.465(9) . ?
C6 C1 1.388(10) . ?
C6 C5 1.394(10) . ?
C1 C2 1.388(10) . ?
C5 H5 0.9300 . ?
C5 C4 1.364(12) . ?
C8 H8 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.377(12) . ?
C4 H4 0.9300 . ?
C4 C3 1.409(14) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C3 H3 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
I1 Bi1 I1 86.670(15) . 2_755 ?
I1 Bi1 I2 87.820(15) . 2_655 ?
I2 Bi1 I1 172.654(16) . . ?
I2 Bi1 I1 87.421(15) . 2_755 ?
I2 Bi1 I1 84.250(15) 2_655 2_755 ?
I2 Bi1 I2 87.250(14) . 2_655 ?
I3 Bi1 I1 172.355(16) . 2_755 ?
I3 Bi1 I1 88.951(16) . . ?
I3 Bi1 I2 89.327(17) . 2_655 ?
I3 Bi1 I2 96.431(17) . . ?
I3 Bi1 I4 93.406(17) . . ?
I4 Bi1 I1 93.291(16) . 2_755 ?
I4 Bi1 I1 96.141(17) . . ?
I4 Bi1 I2 88.549(16) . . ?
I4 Bi1 I2 175.222(16) . 2_655 ?
Bi1 I1 Bi1 93.330(14) . 2_755 ?
Bi1 I2 Bi1 92.750(15) . 2_655 ?
C1 N1 C9 126.4(7) . . ?
C8 N1 C1 107.3(6) . . ?
C8 N1 C9 126.2(7) . . ?
C6 N2 C7 126.5(6) . . ?
C8 N2 C6 107.6(6) . . ?
C8 N2 C7 125.9(7) . . ?
N2 C6 C1 106.5(6) . . ?
N2 C6 C5 131.3(8) . . ?
C1 C6 C5 122.3(8) . . ?
N1 C1 C6 106.8(7) . . ?
N1 C1 C2 131.3(8) . . ?
C6 C1 C2 121.9(7) . . ?
C6 C5 H5 122.2 . . ?
C4 C5 C6 115.6(9) . . ?
C4 C5 H5 122.2 . . ?
N1 C8 H8 124.1 . . ?
N2 C8 N1 111.8(7) . . ?
N2 C8 H8 124.1 . . ?
C1 C2 H2 122.0 . . ?
C3 C2 C1 116.0(9) . . ?
C3 C2 H2 122.0 . . ?
C5 C4 H4 118.7 . . ?
C5 C4 C3 122.5(9) . . ?
C3 C4 H4 118.7 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C3 C4 121.7(9) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?


