# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2293043'
loop_
_audit_author_name
_audit_author_address
'Marlena Gryl'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2023-09-05 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '4-aminopyridinium iodobismuthate'
_chemical_melting_point          ?
_chemical_formula_moiety         'Bi I4, C5 H6 N2'
_chemical_formula_sum            'C5 H6 Bi I4 N2'
_chemical_formula_weight         810.70

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.2049(2)
_cell_length_b                   14.8651(3)
_cell_length_c                   7.60690(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1380.10(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    36350
_cell_measurement_theta_min      2.7190
_cell_measurement_theta_max      32.7220

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.902
_exptl_crystal_F_000             1380
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    21.686
_shelx_estimated_absorpt_T_min   0.220
_shelx_estimated_absorpt_T_max   0.562
_exptl_absorpt_correction_T_min  0.21066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.279
_oxdiff_exptl_absorpt_empirical_full_max 3.513
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(15)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            73188
_diffrn_reflns_av_R_equivalents  0.1002
_diffrn_reflns_av_sigmaI/netI    0.1092
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.338
_diffrn_reflns_theta_max         32.874
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2471
_reflns_number_gt                2236
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT, (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury, (Macrae, 2020)'
_computing_publication_material  'WinGX, (Farrugia, 2012)'

_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)+(0.0207P)²+0.8316P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2471
_refine_ls_number_parameters     60
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0440
_refine_ls_wR_factor_gt          0.0431
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.002
_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 0.5000 0.91581(2) 0.7500 0.01202(5) Uani 1 2 d S T P . .
I2 I 0.36284(2) 0.92054(2) 0.41062(2) 0.01460(5) Uani 1 1 d . . . . .
I3 I 0.33645(2) 0.78509(2) 0.88228(2) 0.01712(5) Uani 1 1 d . . . . .
N8 N 0.5000 0.5855(3) 0.7500 0.0273(10) Uani 1 2 d S T P . .
H8 H 0.5000 0.6447 0.7500 0.033 Uiso 1 2 calc R U P . .
N4 N 0.5000 0.3115(3) 0.7500 0.0349(11) Uani 1 2 d DS T P . .
H4A H 0.546(6) 0.277(5) 0.804(12) 0.042 Uiso 0.5 1 d D U P . .
C6 C 0.5000 0.4003(3) 0.7500 0.0203(9) Uani 1 2 d S T P . .
C7 C 0.4118(3) 0.5411(2) 0.6862(4) 0.0240(6) Uani 1 1 d . . . . .
H7 H 0.3509 0.5740 0.6426 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4097(2) 0.4500(2) 0.6839(4) 0.0210(6) Uani 1 1 d . . . . .
H5 H 0.3477 0.4193 0.6379 0.025 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 I3 2.9619(2) . ?
Bi1 I3 2.9619(2) 3_656 ?
Bi1 I2 3.07772(18) 3_656 ?
Bi1 I2 3.07772(18) . ?
Bi1 I2 3.1958(2) 5_676 ?
Bi1 I2 3.1958(2) 7_576 ?
I2 Bi1 3.1958(2) 5_676 ?
N8 C7 1.353(4) 3_656 ?
N8 C7 1.353(4) . ?
N8 H8 0.8800 . ?
N4 C6 1.320(7) . ?
N4 H4A 0.87(2) . ?
C6 C5 1.418(4) 3_656 ?
C6 C5 1.418(4) . ?
C7 C5 1.355(4) . ?
C7 H7 0.9500 . ?
C5 H5 0.9500 . ?

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
I3 Bi1 I3 98.000(9) . 3_656 ?
I3 Bi1 I2 95.542(5) . 3_656 ?
I3 Bi1 I2 86.183(5) 3_656 3_656 ?
I3 Bi1 I2 86.182(5) . . ?
I3 Bi1 I2 95.542(5) 3_656 . ?
I2 Bi1 I2 177.380(8) 3_656 . ?
I3 Bi1 I2 169.204(6) . 5_676 ?
I3 Bi1 I2 90.946(5) 3_656 5_676 ?
I2 Bi1 I2 91.053(5) 3_656 5_676 ?
I2 Bi1 I2 86.953(5) . 5_676 ?
I3 Bi1 I2 90.946(5) . 7_576 ?
I3 Bi1 I2 169.204(6) 3_656 7_576 ?
I2 Bi1 I2 86.952(5) 3_656 7_576 ?
I2 Bi1 I2 91.052(5) . 7_576 ?
I2 Bi1 I2 80.857(8) 5_676 7_576 ?
Bi1 I2 Bi1 93.047(5) . 5_676 ?
C7 N8 C7 121.6(4) 3_656 . ?
C7 N8 H8 119.2 3_656 . ?
C7 N8 H8 119.2 . . ?
C6 N4 H4A 127(6) . . ?
N4 C6 C5 121.4(2) . 3_656 ?
N4 C6 C5 121.4(2) . . ?
C5 C6 C5 117.3(4) 3_656 . ?
N8 C7 C5 120.5(3) . . ?
N8 C7 H7 119.8 . . ?
C5 C7 H7 119.8 . . ?
C7 C5 C6 120.1(3) . . ?
C7 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?

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
N8 H8 I3 0.88 3.06 3.715(3) 133.0 .
N8 H8 I3 0.88 3.06 3.715(3) 133.0 3_656
N4 H4A I3 0.87(2) 2.93(5) 3.7242(18) 153(9) 5_667
C7 H7 I2 0.95 3.31 3.805(3) 114.5 2_565
C5 H5 I2 0.95 3.10 3.947(3) 149.7 8_655

_refine_diff_density_max         1.169
_refine_diff_density_min         -1.179
_refine_diff_density_rms         0.233

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2293046'
loop_
_audit_author_name
_audit_author_address
'Marlena Gryl'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2023-09-05 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '4-cyanopyridinium iodobismuthate'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Bi2 I8 N4 O'
_chemical_formula_weight         1689.47

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.9874(3)
_cell_length_b                   11.4555(2)
_cell_length_c                   20.4765(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.648(2)
_cell_angle_gamma                90
_cell_volume                     3350.12(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    30883
_cell_measurement_theta_min      2.6640
_cell_measurement_theta_max      33.7030

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.350
_exptl_crystal_F_000             2904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    17.877
_shelx_estimated_absorpt_T_min   0.124
_shelx_estimated_absorpt_T_max   0.329
_exptl_absorpt_correction_T_min  0.18323
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.571
_oxdiff_exptl_absorpt_empirical_full_max 3.630
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            106533
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0872
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.320
_diffrn_reflns_theta_max         33.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11871
_reflns_number_gt                7767
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT, (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury, (Macrae, 2020)'
_computing_publication_material  'WinGX, (Farrugia, 2012)'

_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)+(0.0424P)²+3.7282P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11871
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.46306(2) 0.40703(2) 0.59512(2) 0.04224(7) Uani 1 1 d . . . . .
Bi2 Bi 0.73196(2) 0.28598(2) 0.53551(2) 0.04926(7) Uani 1 1 d . . . . .
I3 I 0.65057(3) 0.53847(3) 0.57106(2) 0.04692(10) Uani 1 1 d . . . . .
I4 I 0.53476(3) 0.17739(3) 0.54515(2) 0.05186(11) Uani 1 1 d . . . . .
I5 I 0.60211(4) 0.35268(4) 0.37737(3) 0.06797(14) Uani 1 1 d . . . . .
I2 I 0.57474(3) 0.37900(4) 0.73714(2) 0.06085(12) Uani 1 1 d . . . . .
I6 I 0.76513(4) 0.06420(4) 0.47487(3) 0.06902(14) Uani 1 1 d . . . . .
I1 I 0.30521(4) 0.28595(5) 0.61564(3) 0.07325(15) Uani 1 1 d . . . . .
I8 I 0.82253(4) 0.20875(5) 0.67597(3) 0.07284(15) Uani 1 1 d . . . . .
I7 I 0.89811(4) 0.41080(5) 0.52413(4) 0.0900(2) Uani 1 1 d . . . . .
N1A N 0.3905(4) 0.0603(4) 0.3235(3) 0.0555(14) Uani 1 1 d . . . . .
C6A C 0.3479(5) 0.0085(6) 0.2628(4) 0.067(2) Uani 1 1 d . . . . .
H6A H 0.2828 0.0089 0.2458 0.080 Uiso 1 1 calc R U . . .
C4A C 0.4956(5) -0.0462(6) 0.2514(4) 0.0611(18) Uani 1 1 d . . . . .
C3A C 0.5379(6) 0.0069(7) 0.3138(4) 0.072(2) Uani 1 1 d . . . . .
H3A H 0.6028 0.0076 0.3320 0.087 Uiso 1 1 calc R U . . .
C2A C 0.4838(5) 0.0581(6) 0.3484(4) 0.0633(18) Uani 1 1 d . . . . .
H2A H 0.5126 0.0926 0.3907 0.076 Uiso 1 1 calc R U . . .
C5A C 0.3986(6) -0.0444(7) 0.2261(4) 0.071(2) Uani 1 1 d . . . . .
H5A H 0.3683 -0.0793 0.1842 0.086 Uiso 1 1 calc R U . . .
C8A C 0.5514(6) -0.1033(7) 0.2142(5) 0.071(2) Uani 1 1 d . . . . .
N2A N 0.5969(7) -0.1499(8) 0.1876(5) 0.099(3) Uani 1 1 d . . . . .
N2B N 0.8350(8) -0.3485(9) 0.2562(7) 0.129(4) Uani 1 1 d . . . . .
O1 O 1.0345(10) 0.2223(9) 0.4510(6) 0.161(4) Uani 1 1 d . . . . .
H1 H 1.0064 0.2837 0.4511 0.193 Uiso 1 1 calc R U . . .
C8B C 0.8546(8) -0.2598(10) 0.2794(7) 0.101(4) Uani 1 1 d . . . . .
C6B C 0.8650(7) 0.0574(10) 0.3077(6) 0.094(3) Uani 1 1 d . . . . .
H6B H 0.8349 0.1246 0.2867 0.113 Uiso 1 1 calc R U . . .
N1B N 0.9359(6) 0.0645(10) 0.3659(5) 0.098(3) Uani 1 1 d . . . . .
H1B H 0.9541 0.1322 0.3831 0.118 Uiso 1 1 calc R U . . .
C2B C 0.9781(8) -0.028(2) 0.3972(8) 0.143(6) Uani 1 1 d . . . . .
H2B H 1.0259 -0.0202 0.4384 0.171 Uiso 1 1 calc R U . . .
C3B C 0.9537(10) -0.1373(15) 0.3710(8) 0.130(5) Uani 1 1 d . . . . .
H3B H 0.9848 -0.2030 0.3934 0.156 Uiso 1 1 calc R U . . .
C4B C 0.8811(6) -0.1475(9) 0.3101(6) 0.080(3) Uani 1 1 d . . . . .
C5B C 0.8378(6) -0.0478(8) 0.2799(5) 0.076(2) Uani 1 1 d . . . . .
H5B H 0.7886 -0.0529 0.2393 0.092 Uiso 1 1 calc R U . . .
C1 C 1.1220(11) 0.2461(12) 0.4393(8) 0.154(7) Uani 1 1 d . . . . .
H1A H 1.1123 0.2993 0.4016 0.184 Uiso 1 1 calc R U . . .
H1C H 1.1482 0.1747 0.4288 0.184 Uiso 1 1 calc R U . . .
H1D H 1.1643 0.2804 0.4797 0.184 Uiso 1 1 calc R U . . .
C7A C 0.3349(6) 0.1168(8) 0.3624(5) 0.083(3) Uani 1 1 d . . . . .
H7AA H 0.2944 0.1741 0.3342 0.124 Uiso 1 1 calc R U . . .
H7AB H 0.3760 0.1541 0.4022 0.124 Uiso 1 1 calc R U . . .
H7AC H 0.2979 0.0591 0.3764 0.124 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 2.8811(5) . ?
Bi1 I2 2.9002(5) . ?
Bi1 I5 3.0301(5) 3_666 ?
Bi1 I4 3.1286(4) . ?
Bi1 I3 3.3537(4) . ?
Bi1 I3 3.3697(5) 3_666 ?
Bi2 I8 2.9206(6) . ?
Bi2 I6 2.9357(5) . ?
Bi2 I7 2.9414(6) . ?
Bi2 I4 3.2672(5) . ?
Bi2 I3 3.3049(4) . ?
Bi2 I5 3.3220(6) . ?
I3 Bi1 3.3697(5) 3_666 ?
I5 Bi1 3.0302(5) 3_666 ?
N1A C2A 1.334(9) . ?
N1A C6A 1.351(9) . ?
N1A C7A 1.468(10) . ?
C6A C5A 1.363(12) . ?
C6A H6A 0.9300 . ?
C4A C3A 1.383(11) . ?
C4A C5A 1.388(11) . ?
C4A C8A 1.448(12) . ?
C3A C2A 1.362(12) . ?
C3A H3A 0.9300 . ?
C2A H2A 0.9300 . ?
C5A H5A 0.9300 . ?
C8A N2A 1.127(11) . ?
N2B C8B 1.122(15) . ?
O1 C1 1.429(18) . ?
O1 H1 0.8200 . ?
C8B C4B 1.434(16) . ?
C6B N1B 1.337(13) . ?
C6B C5B 1.342(13) . ?
C6B H6B 0.9300 . ?
N1B C2B 1.303(18) . ?
N1B H1B 0.8600 . ?
C2B C3B 1.36(2) . ?
C2B H2B 0.9300 . ?
C3B C4B 1.389(18) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.366(12) . ?
C5B H5B 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 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 I2 92.880(16) . . ?
I1 Bi1 I5 94.876(18) . 3_666 ?
I2 Bi1 I5 91.989(16) . 3_666 ?
I1 Bi1 I4 91.234(15) . . ?
I2 Bi1 I4 94.807(15) . . ?
I5 Bi1 I4 170.622(15) 3_666 . ?
I1 Bi1 I3 177.897(15) . . ?
I2 Bi1 I3 86.699(13) . . ?
I5 Bi1 I3 87.198(14) 3_666 . ?
I4 Bi1 I3 86.750(11) . . ?
I1 Bi1 I3 92.895(15) . 3_666 ?
I2 Bi1 I3 173.971(14) . 3_666 ?
I5 Bi1 I3 85.797(13) 3_666 3_666 ?
I4 Bi1 I3 86.796(12) . 3_666 ?
I3 Bi1 I3 87.592(11) . 3_666 ?
I8 Bi2 I6 93.819(17) . . ?
I8 Bi2 I7 94.21(2) . . ?
I6 Bi2 I7 97.539(18) . . ?
I8 Bi2 I4 89.087(16) . . ?
I6 Bi2 I4 88.186(14) . . ?
I7 Bi2 I4 173.177(15) . . ?
I8 Bi2 I3 98.085(15) . . ?
I6 Bi2 I3 166.344(16) . . ?
I7 Bi2 I3 88.272(15) . . ?
I4 Bi2 I3 85.348(11) . . ?
I8 Bi2 I5 171.730(18) . . ?
I6 Bi2 I5 84.897(15) . . ?
I7 Bi2 I5 94.06(2) . . ?
I4 Bi2 I5 82.711(15) . . ?
I3 Bi2 I5 82.363(12) . . ?
Bi2 I3 Bi1 91.206(11) . . ?
Bi2 I3 Bi1 92.697(12) . 3_666 ?
Bi1 I3 Bi1 92.407(11) . 3_666 ?
Bi1 I4 Bi2 96.102(12) . . ?
Bi1 I5 Bi2 98.878(15) 3_666 . ?
C2A N1A C6A 119.5(7) . . ?
C2A N1A C7A 120.1(7) . . ?
C6A N1A C7A 120.3(6) . . ?
N1A C6A C5A 121.0(7) . . ?
N1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
C3A C4A C5A 118.3(8) . . ?
C3A C4A C8A 120.6(7) . . ?
C5A C4A C8A 121.1(8) . . ?
C2A C3A C4A 119.4(7) . . ?
C2A C3A H3A 120.3 . . ?
C4A C3A H3A 120.3 . . ?
N1A C2A C3A 121.9(7) . . ?
N1A C2A H2A 119.0 . . ?
C3A C2A H2A 119.0 . . ?
C6A C5A C4A 119.8(7) . . ?
C6A C5A H5A 120.1 . . ?
C4A C5A H5A 120.1 . . ?
N2A C8A C4A 177.3(10) . . ?
C1 O1 H1 109.5 . . ?
N2B C8B C4B 178.8(16) . . ?
N1B C6B C5B 119.4(11) . . ?
N1B C6B H6B 120.3 . . ?
C5B C6B H6B 120.3 . . ?
C2B N1B C6B 121.6(12) . . ?
C2B N1B H1B 119.2 . . ?
C6B N1B H1B 119.2 . . ?
N1B C2B C3B 121.4(14) . . ?
N1B C2B H2B 119.3 . . ?
C3B C2B H2B 119.3 . . ?
C2B C3B C4B 118.3(13) . . ?
C2B C3B H3B 120.9 . . ?
C4B C3B H3B 120.9 . . ?
C5B C4B C3B 118.2(11) . . ?
C5B C4B C8B 121.4(11) . . ?
C3B C4B C8B 120.5(11) . . ?
C6B C5B C4B 121.1(10) . . ?
C6B C5B H5B 119.5 . . ?
C4B C5B H5B 119.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
O1 C1 H1D 109.5 . . ?
H1A C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
N1A C7A H7AA 109.5 . . ?
N1A C7A H7AB 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
N1A C7A H7AC 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?

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
C2A N1A C6A C5A -1.0(11) . . . . ?
C7A N1A C6A C5A -179.9(8) . . . . ?
C5A C4A C3A C2A 0.5(11) . . . . ?
C8A C4A C3A C2A -178.8(7) . . . . ?
C6A N1A C2A C3A 1.3(11) . . . . ?
C7A N1A C2A C3A -179.8(8) . . . . ?
C4A C3A C2A N1A -1.0(12) . . . . ?
N1A C6A C5A C4A 0.5(12) . . . . ?
C3A C4A C5A C6A -0.2(11) . . . . ?
C8A C4A C5A C6A 179.0(8) . . . . ?
C5B C6B N1B C2B -1.5(15) . . . . ?
C6B N1B C2B C3B 1.9(19) . . . . ?
N1B C2B C3B C4B -1(2) . . . . ?
C2B C3B C4B C5B -0.3(17) . . . . ?
C2B C3B C4B C8B 178.1(11) . . . . ?
N1B C6B C5B C4B 0.2(14) . . . . ?
C3B C4B C5B C6B 0.7(14) . . . . ?
C8B C4B C5B C6B -177.7(9) . . . . ?

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
C6A H6A I2 0.93 3.33 4.170(8) 151.7 4_565
C3A H3A I6 0.93 3.25 4.012(8) 140.1 .
C2A H2A I4 0.93 3.23 4.100(8) 157.0 .
C2A H2A I5 0.93 3.31 3.774(7) 113.0 .
O1 H1 I7 0.82 2.91 3.597(10) 142.8 .
C6B H6B N2B 0.93 2.45 3.079(16) 125.2 2_655
N1B H1B O1 0.86 1.85 2.631(15) 149.5 .
C2B H2B I6 0.93 3.14 3.966(13) 149.2 3_756
C3B H3B I7 0.93 3.13 4.058(13) 175.4 3_756
C1 H1D I1 0.96 2.94 3.843(14) 157.1 1_655
C7A H7AB I4 0.96 3.17 4.082(10) 158.3 .

_refine_diff_density_max         1.772
_refine_diff_density_min         -1.325
_refine_diff_density_rms         0.185

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2293044'
loop_
_audit_author_name
_audit_author_address
'Marlena Gryl'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2023-09-05 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '4-methylpyridinium iodobismuthate'
_chemical_melting_point          ?
_chemical_formula_moiety         'Bi2 I9, 3(C6 H8 N)'
_chemical_formula_sum            'C18 H24 Bi2 I9 N3'
_chemical_formula_weight         1842.46

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.24430(10)
_cell_length_b                   10.64010(10)
_cell_length_c                   37.9400(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3731.79(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    134129
_cell_measurement_theta_min      2.1780
_cell_measurement_theta_max      33.427

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.279
_exptl_crystal_F_000             3184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    16.877
_exptl_absorpt_correction_T_min  0.20160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.624
_oxdiff_exptl_absorpt_empirical_full_max 2.257
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            99465
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.1009
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_theta_min         2.195
_diffrn_reflns_theta_max         33.386
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             13295
_reflns_number_gt                11821
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.887
_reflns_Friedel_fraction_full    1.000

_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT, (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury, (Macrae, 2020)'
_computing_publication_material  'WinGX, (Farrugia, 2012)'
_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)+(0.0649P)²] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 4600 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         13295
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_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 0.22393(4) 0.37324(3) 0.32976(2) 0.01715(8) Uani 1 1 d . . . . .
Bi2 Bi 0.29163(4) 0.58847(3) 0.42159(2) 0.01834(8) Uani 1 1 d . . . . .
I4 I 0.03686(7) 0.59920(6) 0.36448(2) 0.02000(12) Uani 1 1 d . . . . .
I5 I 0.49813(7) 0.55631(6) 0.35132(2) 0.01969(12) Uani 1 1 d . . . . .
I6 I 0.23406(7) 0.28701(6) 0.41199(2) 0.02058(13) Uani 1 1 d . . . . .
I9 I 0.55111(7) 0.54325(6) 0.46683(2) 0.02255(13) Uani 1 1 d . . . . .
I7 I 0.08743(8) 0.60066(7) 0.48028(2) 0.02504(14) Uani 1 1 d . . . . .
I1 I -0.04704(7) 0.24442(6) 0.31250(2) 0.02330(13) Uani 1 1 d . . . . .
I3 I 0.43650(7) 0.16874(6) 0.31514(2) 0.02422(14) Uani 1 1 d . . . . .
I2 I 0.24612(8) 0.48098(7) 0.25872(2) 0.02581(14) Uani 1 1 d . . . . .
I8 I 0.33707(8) 0.86251(7) 0.41685(3) 0.0360(2) Uani 1 1 d . . . . .
N1A N -0.0842(11) 0.9009(10) 0.4467(3) 0.031(2) Uani 1 1 d . . . . .
H1A H -0.049599 0.899533 0.468345 0.037 Uiso 1 1 calc R U . . .
C4B C 0.2264(12) 0.9701(10) 0.2529(3) 0.024(2) Uani 1 1 d . . . . .
C6A C -0.0309(12) 0.9827(10) 0.4238(3) 0.026(2) Uani 1 1 d . . . . .
H6A H 0.043864 1.038981 0.430609 0.032 Uiso 1 1 calc R U . . .
C3C C 0.8276(11) 0.3372(10) 0.4263(3) 0.023(2) Uani 1 1 d . . . . .
H3C H 0.901708 0.397536 0.430090 0.028 Uiso 1 1 calc R U . . .
C2C C 0.7607(12) 0.3318(11) 0.3948(3) 0.026(2) Uani 1 1 d . . . . .
H2C H 0.791023 0.386085 0.376295 0.031 Uiso 1 1 calc R U . . .
N1B N 0.3143(14) 0.7961(9) 0.3014(4) 0.043(3) Uani 1 1 d . . . . .
H1B H 0.345072 0.741462 0.317107 0.051 Uiso 1 1 calc R U . . .
N1C N 0.6513(12) 0.2506(10) 0.3891(3) 0.038(3) Uani 1 1 d . . . . .
H1C H 0.606861 0.250407 0.368544 0.046 Uiso 1 1 calc R U . . .
C4A C -0.1910(12) 0.9003(11) 0.3800(3) 0.025(2) Uani 1 1 d . . . . .
C3B C 0.3510(13) 0.9023(12) 0.2477(3) 0.032(2) Uani 1 1 d . . . . .
H3B H 0.407400 0.915535 0.227075 0.039 Uiso 1 1 calc R U . . .
C2A C -0.1901(13) 0.8194(10) 0.4378(3) 0.030(2) Uani 1 1 d . . . . .
H2A H -0.225766 0.762494 0.455029 0.036 Uiso 1 1 calc R U . . .
C3A C -0.2455(11) 0.8172(10) 0.4054(3) 0.026(2) Uani 1 1 d . . . . .
H3A H -0.320971 0.760173 0.399649 0.031 Uiso 1 1 calc R U . . .
C4C C 0.7891(14) 0.2550(11) 0.4535(3) 0.032(2) Uani 1 1 d . . . . .
C7A C -0.2510(18) 0.8984(14) 0.3429(3) 0.046(3) Uani 1 1 d . . . . .
H7A1 H -0.355715 0.912377 0.343623 0.069 Uiso 1 1 calc R U . . .
H7A2 H -0.230990 0.816601 0.332039 0.069 Uiso 1 1 calc R U . . .
H7A3 H -0.205106 0.964906 0.328942 0.069 Uiso 1 1 calc R U . . .
C2B C 0.3926(15) 0.8174(12) 0.2716(4) 0.040(3) Uani 1 1 d . . . . .
H2B H 0.478893 0.770951 0.267754 0.048 Uiso 1 1 calc R U . . .
C6B C 0.1908(14) 0.8582(12) 0.3068(4) 0.036(3) Uani 1 1 d . . . . .
H6B H 0.135562 0.841308 0.327323 0.044 Uiso 1 1 calc R U . . .
C6C C 0.6088(13) 0.1690(12) 0.4145(5) 0.041(3) Uani 1 1 d . . . . .
H6C H 0.532946 0.111186 0.409833 0.049 Uiso 1 1 calc R U . . .
C5A C -0.0854(13) 0.9850(10) 0.3901(3) 0.029(2) Uani 1 1 d . . . . .
H5A H -0.050326 1.045127 0.373679 0.034 Uiso 1 1 calc R U . . .
C5B C 0.1421(12) 0.9462(11) 0.2831(4) 0.029(2) Uani 1 1 d . . . . .
H5B H 0.053866 0.989796 0.286925 0.035 Uiso 1 1 calc R U . . .
C7B C 0.1808(13) 1.0708(11) 0.2279(3) 0.029(2) Uani 1 1 d . . . . .
H7B1 H 0.216935 1.152155 0.236176 0.044 Uiso 1 1 calc R U . . .
H7B2 H 0.074992 1.073195 0.226547 0.044 Uiso 1 1 calc R U . . .
H7B3 H 0.220623 1.053089 0.204450 0.044 Uiso 1 1 calc R U . . .
C5C C 0.6738(15) 0.1693(12) 0.4466(4) 0.044(4) Uani 1 1 d . . . . .
H5C H 0.642606 0.112673 0.464392 0.053 Uiso 1 1 calc R U . . .
C7C C 0.865(2) 0.2619(18) 0.4886(4) 0.062(5) Uani 1 1 d . . . . .
H7C1 H 0.969761 0.262363 0.484874 0.093 Uiso 1 1 calc R U . . .
H7C2 H 0.838097 0.188791 0.502883 0.093 Uiso 1 1 calc R U . . .
H7C3 H 0.835976 0.339007 0.500830 0.093 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 2.9296(7) . ?
Bi1 I2 2.9361(8) . ?
Bi1 I3 2.9840(8) . ?
Bi1 I4 3.2412(7) . ?
Bi1 I6 3.2532(7) . ?
Bi1 I5 3.2998(7) . ?
Bi2 I7 2.9219(8) . ?
Bi2 I8 2.9514(8) . ?
Bi2 I9 2.9885(8) . ?
Bi2 I4 3.2024(7) . ?
Bi2 I6 3.2718(7) . ?
Bi2 I5 3.2968(7) . ?
N1A C6A 1.325(15) . ?
N1A C2A 1.350(15) . ?
N1A H1A 0.8800 . ?
C4B C3B 1.374(16) . ?
C4B C5B 1.407(16) . ?
C4B C7B 1.492(16) . ?
C6A C5A 1.375(16) . ?
C6A H6A 0.9500 . ?
C3C C2C 1.348(15) . ?
C3C C4C 1.399(16) . ?
C3C H3C 0.9500 . ?
C2C N1C 1.348(16) . ?
C2C H2C 0.9500 . ?
N1B C2B 1.36(2) . ?
N1B C6B 1.335(18) . ?
N1B H1B 0.8800 . ?
N1C C6C 1.356(19) . ?
N1C H1C 0.8800 . ?
C4A C5A 1.383(17) . ?
C4A C3A 1.404(16) . ?
C4A C7A 1.513(16) . ?
C3B C2B 1.34(2) . ?
C3B H3B 0.9500 . ?
C2A C3A 1.332(17) . ?
C2A H2A 0.9500 . ?
C3A H3A 0.9500 . ?
C4C C5C 1.43(2) . ?
C4C C7C 1.506(19) . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C2B H2B 0.9500 . ?
C6B C5B 1.374(18) . ?
C6B H6B 0.9500 . ?
C6C C5C 1.36(2) . ?
C6C H6C 0.9500 . ?
C5A H5A 0.9500 . ?
C5B H5B 0.9500 . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
C5C H5C 0.9500 . ?
C7C H7C1 0.9800 . ?
C7C H7C2 0.9800 . ?
C7C H7C3 0.9800 . ?

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 I2 92.13(2) . . ?
I1 Bi1 I3 100.39(2) . . ?
I2 Bi1 I3 93.90(2) . . ?
I1 Bi1 I4 88.95(2) . . ?
I2 Bi1 I4 96.93(2) . . ?
I3 Bi1 I4 165.43(2) . . ?
I1 Bi1 I6 96.14(2) . . ?
I2 Bi1 I6 171.27(2) . . ?
I3 Bi1 I6 87.35(2) . . ?
I4 Bi1 I6 80.497(18) . . ?
I1 Bi1 I5 171.28(2) . . ?
I2 Bi1 I5 86.76(2) . . ?
I3 Bi1 I5 88.321(19) . . ?
I4 Bi1 I5 82.603(18) . . ?
I6 Bi1 I5 84.644(18) . . ?
I7 Bi2 I8 95.43(3) . . ?
I7 Bi2 I9 95.05(2) . . ?
I8 Bi2 I9 94.58(2) . . ?
I7 Bi2 I4 92.23(2) . . ?
I8 Bi2 I4 91.61(2) . . ?
I9 Bi2 I4 169.95(2) . . ?
I7 Bi2 I6 91.34(2) . . ?
I8 Bi2 I6 170.03(3) . . ?
I9 Bi2 I6 92.10(2) . . ?
I4 Bi2 I6 80.792(18) . . ?
I7 Bi2 I5 174.21(2) . . ?
I8 Bi2 I5 88.33(2) . . ?
I9 Bi2 I5 89.022(19) . . ?
I4 Bi2 I5 83.243(18) . . ?
I6 Bi2 I5 84.398(18) . . ?
Bi2 I4 Bi1 81.728(17) . . ?
Bi2 I5 Bi1 79.451(17) . . ?
Bi1 I6 Bi2 80.500(16) . . ?
C6A N1A C2A 121.8(11) . . ?
C6A N1A H1A 119.1 . . ?
C2A N1A H1A 119.1 . . ?
C3B C4B C5B 119.1(11) . . ?
C3B C4B C7B 121.5(11) . . ?
C5B C4B C7B 119.4(10) . . ?
N1A C6A C5A 119.1(10) . . ?
N1A C6A H6A 120.5 . . ?
C5A C6A H6A 120.5 . . ?
C2C C3C C4C 120.8(11) . . ?
C2C C3C H3C 119.6 . . ?
C4C C3C H3C 119.6 . . ?
N1C C2C C3C 120.9(11) . . ?
N1C C2C H2C 119.5 . . ?
C3C C2C H2C 119.5 . . ?
C2B N1B C6B 119.9(12) . . ?
C2B N1B H1B 120.0 . . ?
C6B N1B H1B 120.0 . . ?
C6C N1C C2C 120.9(11) . . ?
C6C N1C H1C 119.6 . . ?
C2C N1C H1C 119.6 . . ?
C5A C4A C3A 118.2(11) . . ?
C5A C4A C7A 121.8(12) . . ?
C3A C4A C7A 120.0(11) . . ?
C2B C3B C4B 119.9(12) . . ?
C2B C3B H3B 120.1 . . ?
C4B C3B H3B 120.1 . . ?
C3A C2A N1A 121.5(11) . . ?
C3A C2A H2A 119.3 . . ?
N1A C2A H2A 119.3 . . ?
C2A C3A C4A 119.0(11) . . ?
C2A C3A H3A 120.5 . . ?
C4A C3A H3A 120.5 . . ?
C3C C4C C5C 117.0(12) . . ?
C3C C4C C7C 120.2(14) . . ?
C5C C4C C7C 122.7(14) . . ?
C4A C7A H7A1 109.5 . . ?
C4A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C4A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
N1B C2B C3B 121.6(12) . . ?
N1B C2B H2B 119.2 . . ?
C3B C2B H2B 119.2 . . ?
N1B C6B C5B 121.2(13) . . ?
N1B C6B H6B 119.4 . . ?
C5B C6B H6B 119.4 . . ?
N1C C6C C5C 120.6(12) . . ?
N1C C6C H6C 119.7 . . ?
C5C C6C H6C 119.7 . . ?
C6A C5A C4A 120.4(11) . . ?
C6A C5A H5A 119.8 . . ?
C4A C5A H5A 119.8 . . ?
C6B C5B C4B 118.3(11) . . ?
C6B C5B H5B 120.9 . . ?
C4B C5B H5B 120.9 . . ?
C4B C7B H7B1 109.5 . . ?
C4B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
C4B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
C6C C5C C4C 119.8(12) . . ?
C6C C5C H5C 120.1 . . ?
C4C C5C H5C 120.1 . . ?
C4C C7C H7C1 109.5 . . ?
C4C C7C H7C2 109.5 . . ?
H7C1 C7C H7C2 109.5 . . ?
C4C C7C H7C3 109.5 . . ?
H7C1 C7C H7C3 109.5 . . ?
H7C2 C7C H7C3 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
_geom_hbond_publ_flag
N1A H1A I9 0.88 2.70 3.560(10) 166.0 4_466 yes
C6A H6A I6 0.95 3.25 4.085(11) 147.9 1_565 yes
C2C H2C I4 0.95 3.24 3.991(12) 137.2 1_655 yes
C2C H2C I1 0.95 3.22 3.710(11) 114.0 1_655 yes
N1B H1B I5 0.88 2.75 3.604(11) 163.6 . yes
N1C H1C I3 0.88 2.71 3.545(11) 159.0 . yes
C2A H2A I9 0.95 3.15 3.946(12) 143.0 1_455 yes
C3A H3A I5 0.95 3.30 4.187(11) 157.1 1_455 yes
C6B H6B I4 0.95 3.07 3.797(13) 134.0 . yes
C6C H6C I8 0.95 3.22 4.118(13) 158.9 1_545 yes
C5A H5A I1 0.95 3.14 4.051(12) 160.3 1_565 yes
C5B H5B I1 0.95 3.03 3.791(11) 138.7 1_565 yes
C5B H5B I2 0.95 3.27 3.941(12) 129.2 3 yes
C5C H5C I7 0.95 3.13 4.073(13) 170.1 4_556 yes

_refine_diff_density_max         3.440
_refine_diff_density_min         -3.495
_refine_diff_density_rms         0.339

####################################################################### 
# 
# 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_4dmapyBiI3
_database_code_depnum_ccdc_archive 'CCDC 2293045'
loop_
_audit_author_name
_audit_author_address
'Marlena Gryl'
;Jagiellonian University
Poland
;
_audit_update_record             
;
2023-09-05 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        '4(N,N-dimethylamino)pyridinium iodobismuthate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Bi2 I10, 4(C7 H11 N2)'
_chemical_formula_sum            'C28 H44 Bi2 I10 N8'
_chemical_formula_weight         2179.67

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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   17.9971(6)
_cell_length_b                   20.3282(7)
_cell_length_c                   13.9362(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5098.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    73204
_cell_measurement_theta_min      2.1130
_cell_measurement_theta_max      33.6490

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.840
_exptl_crystal_F_000             3856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    12.977
_shelx_estimated_absorpt_T_min   0.181
_shelx_estimated_absorpt_T_max   0.697
_exptl_absorpt_correction_T_min  0.10941
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.441
_oxdiff_exptl_absorpt_empirical_full_max 8.537
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      130.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            188105
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.102
_diffrn_reflns_theta_max         33.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9690
_reflns_number_gt                7777
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT, (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury, (Macrae, 2020)'
_computing_publication_material  'WinGX, (Farrugia, 2012)'
_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+12.5139P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.000061(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9690
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0269
_refine_ls_wR_factor_ref         0.0622
_refine_ls_wR_factor_gt          0.0579
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.019
_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 0.51895(2) 0.250000 0.78834(2) 0.01720(4) Uani 1 2 d S T P . .
Bi2 Bi 0.48200(2) 0.250000 0.44862(2) 0.01836(4) Uani 1 2 d S T P . .
I4 I 0.62571(2) 0.250000 0.59315(2) 0.02073(6) Uani 1 2 d S T P . .
I3 I 0.37821(2) 0.250000 0.64429(2) 0.02090(6) Uani 1 2 d S T P . .
I6 I 0.48578(2) 0.39987(2) 0.45940(2) 0.02688(5) Uani 1 1 d . . . . .
I8 I 0.52037(2) 0.40087(2) 0.78301(2) 0.02397(5) Uani 1 1 d . . . . .
I2 I 0.65935(2) 0.250000 0.89188(3) 0.03405(8) Uani 1 2 d S T P . .
I5 I 0.57473(2) 0.250000 0.27589(3) 0.04245(9) Uani 1 2 d S T P . .
I1 I 0.42092(3) 0.250000 0.95648(3) 0.04612(10) Uani 1 2 d S T P . .
I7 I 0.34311(2) 0.250000 0.34226(3) 0.04845(11) Uani 1 2 d S T P . .
C3A C 0.21749(18) 0.47381(16) 0.6475(2) 0.0228(6) Uani 1 1 d . . . . .
H3A H 0.165283 0.467139 0.650177 0.027 Uiso 1 1 calc R U . . .
N2A N 0.20384(15) 0.59275(14) 0.6421(2) 0.0248(5) Uani 1 1 d . . . . .
C6A C 0.36866(18) 0.48934(16) 0.6403(2) 0.0246(6) Uani 1 1 d . . . . .
H6A H 0.421199 0.493629 0.638192 0.029 Uiso 1 1 calc R U . . .
C8A C 0.2352(2) 0.65791(16) 0.6248(3) 0.0294(7) Uani 1 1 d . . . . .
H8A1 H 0.263560 0.671981 0.681142 0.044 Uiso 1 1 calc R U . . .
H8A2 H 0.194881 0.689279 0.612704 0.044 Uiso 1 1 calc R U . . .
H8A3 H 0.268058 0.656202 0.568789 0.044 Uiso 1 1 calc R U . . .
C4B C 0.79295(18) 0.51531(16) 0.6050(2) 0.0222(6) Uani 1 1 d . . . . .
N2B N 0.84081(17) 0.56469(15) 0.6000(2) 0.0301(6) Uani 1 1 d . . . . .
N1A N 0.33785(16) 0.42855(14) 0.6426(2) 0.0266(6) Uani 1 1 d . . . . .
H1A H 0.366503 0.393494 0.640899 0.032 Uiso 1 1 calc R U . . .
C4A C 0.24688(17) 0.53904(15) 0.6436(2) 0.0195(6) Uani 1 1 d . . . . .
N1B N 0.69071(17) 0.41310(15) 0.6145(2) 0.0302(6) Uani 1 1 d . . . . .
H1B H 0.658267 0.380781 0.617607 0.036 Uiso 1 1 calc R U . . .
C2B C 0.66673(19) 0.47560(18) 0.6088(2) 0.0271(7) Uani 1 1 d . . . . .
H2B H 0.614807 0.483968 0.607424 0.033 Uiso 1 1 calc R U . . .
C3B C 0.71432(18) 0.52674(16) 0.6049(2) 0.0236(6) Uani 1 1 d . . . . .
H3B H 0.695734 0.570432 0.602028 0.028 Uiso 1 1 calc R U . . .
C2A C 0.26394(19) 0.42163(16) 0.6474(2) 0.0247(6) Uani 1 1 d . . . . .
H2A H 0.243514 0.378606 0.650843 0.030 Uiso 1 1 calc R U . . .
C5B C 0.81548(19) 0.44806(17) 0.6104(2) 0.0278(7) Uani 1 1 d . . . . .
H5B H 0.866834 0.437263 0.610166 0.033 Uiso 1 1 calc R U . . .
C7A C 0.12271(19) 0.5875(2) 0.6497(3) 0.0370(9) Uani 1 1 d . . . . .
H7A1 H 0.102572 0.569834 0.589664 0.055 Uiso 1 1 calc R U . . .
H7A2 H 0.101536 0.631166 0.661644 0.055 Uiso 1 1 calc R U . . .
H7A3 H 0.109855 0.558044 0.702811 0.055 Uiso 1 1 calc R U . . .
C7B C 0.8146(3) 0.63270(19) 0.5991(3) 0.0442(10) Uani 1 1 d . . . . .
H7B1 H 0.781752 0.639419 0.543816 0.066 Uiso 1 1 calc R U . . .
H7B2 H 0.857183 0.662542 0.594414 0.066 Uiso 1 1 calc R U . . .
H7B3 H 0.787169 0.641758 0.658385 0.066 Uiso 1 1 calc R U . . .
C8B C 0.9208(2) 0.5551(2) 0.5977(4) 0.0516(12) Uani 1 1 d . . . . .
H8B1 H 0.932215 0.513600 0.565136 0.077 Uiso 1 1 calc R U . . .
H8B2 H 0.939981 0.553638 0.663499 0.077 Uiso 1 1 calc R U . . .
H8B3 H 0.944110 0.591604 0.563045 0.077 Uiso 1 1 calc R U . . .
C5A C 0.32579(17) 0.54413(15) 0.6409(2) 0.0204(6) Uani 1 1 d . . . . .
H5A H 0.348541 0.586286 0.639631 0.025 Uiso 1 1 calc R U . . .
C6B C 0.7639(2) 0.39949(17) 0.6157(3) 0.0290(7) Uani 1 1 d . . . . .
H6B H 0.779819 0.355036 0.620280 0.035 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 I2 2.9098(4) . ?
Bi1 I1 2.9331(4) . ?
Bi1 I8 3.0678(2) 8_565 ?
Bi1 I8 3.0678(2) . ?
Bi1 I3 3.2320(3) . ?
Bi1 I4 3.3304(3) . ?
Bi2 I7 2.9061(4) . ?
Bi2 I5 2.9292(4) . ?
Bi2 I6 3.0511(2) 8_565 ?
Bi2 I6 3.0511(2) . ?
Bi2 I4 3.2782(3) . ?
Bi2 I3 3.3053(3) . ?
C3A C2A 1.350(5) . ?
C3A C4A 1.429(4) . ?
C3A H3A 0.9500 . ?
N2A C4A 1.339(4) . ?
N2A C8A 1.460(4) . ?
N2A C7A 1.468(4) . ?
C6A N1A 1.355(4) . ?
C6A C5A 1.355(4) . ?
C6A H6A 0.9500 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C4B N2B 1.325(4) . ?
C4B C5B 1.428(5) . ?
C4B C3B 1.434(5) . ?
N2B C8B 1.453(5) . ?
N2B C7B 1.461(5) . ?
N1A C2A 1.339(4) . ?
N1A H1A 0.8800 . ?
C4A C5A 1.424(4) . ?
N1B C2B 1.344(5) . ?
N1B C6B 1.347(5) . ?
N1B H1B 0.8800 . ?
C2B C3B 1.348(5) . ?
C2B H2B 0.9500 . ?
C3B H3B 0.9500 . ?
C2A H2A 0.9500 . ?
C5B C6B 1.357(5) . ?
C5B H5B 0.9500 . ?
C7A H7A1 0.9800 . ?
C7A H7A2 0.9800 . ?
C7A H7A3 0.9800 . ?
C7B H7B1 0.9800 . ?
C7B H7B2 0.9800 . ?
C7B H7B3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C5A H5A 0.9500 . ?
C6B H6B 0.9500 . ?

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
I2 Bi1 I1 97.246(14) . . ?
I2 Bi1 I8 90.272(5) . 8_565 ?
I1 Bi1 I8 91.396(5) . 8_565 ?
I2 Bi1 I8 90.273(5) . . ?
I1 Bi1 I8 91.395(5) . . ?
I8 Bi1 I8 177.066(10) 8_565 . ?
I2 Bi1 I3 171.332(11) . . ?
I1 Bi1 I3 91.422(12) . . ?
I8 Bi1 I3 89.514(5) 8_565 . ?
I8 Bi1 I3 89.513(5) . . ?
I2 Bi1 I4 84.497(11) . . ?
I1 Bi1 I4 178.258(12) . . ?
I8 Bi1 I4 88.590(5) 8_565 . ?
I8 Bi1 I4 88.592(5) . . ?
I3 Bi1 I4 86.836(9) . . ?
I7 Bi2 I5 94.065(14) . . ?
I7 Bi2 I6 92.539(5) . 8_565 ?
I5 Bi2 I6 91.589(5) . 8_565 ?
I7 Bi2 I6 92.539(5) . . ?
I5 Bi2 I6 91.589(5) . . ?
I6 Bi2 I6 173.804(11) 8_565 . ?
I7 Bi2 I4 172.758(13) . . ?
I5 Bi2 I4 93.176(11) . . ?
I6 Bi2 I4 87.257(5) 8_565 . ?
I6 Bi2 I4 87.258(5) . . ?
I7 Bi2 I3 86.257(12) . . ?
I5 Bi2 I3 179.678(12) . . ?
I6 Bi2 I3 88.396(5) 8_565 . ?
I6 Bi2 I3 88.396(5) . . ?
I4 Bi2 I3 86.502(8) . . ?
Bi2 I4 Bi1 92.675(8) . . ?
Bi1 I3 Bi2 93.988(8) . . ?
C2A C3A C4A 120.0(3) . . ?
C2A C3A H3A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C4A N2A C8A 121.3(3) . . ?
C4A N2A C7A 121.0(3) . . ?
C8A N2A C7A 117.5(3) . . ?
N1A C6A C5A 121.1(3) . . ?
N1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
N2A C8A H8A1 109.5 . . ?
N2A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
N2A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
N2B C4B C5B 122.9(3) . . ?
N2B C4B C3B 121.3(3) . . ?
C5B C4B C3B 115.8(3) . . ?
C4B N2B C8B 122.9(3) . . ?
C4B N2B C7B 120.5(3) . . ?
C8B N2B C7B 116.6(3) . . ?
C2A N1A C6A 120.2(3) . . ?
C2A N1A H1A 119.9 . . ?
C6A N1A H1A 119.9 . . ?
N2A C4A C5A 121.1(3) . . ?
N2A C4A C3A 122.9(3) . . ?
C5A C4A C3A 116.0(3) . . ?
C2B N1B C6B 120.6(3) . . ?
C2B N1B H1B 119.7 . . ?
C6B N1B H1B 119.7 . . ?
N1B C2B C3B 121.8(3) . . ?
N1B C2B H2B 119.1 . . ?
C3B C2B H2B 119.1 . . ?
C2B C3B C4B 120.1(3) . . ?
C2B C3B H3B 119.9 . . ?
C4B C3B H3B 119.9 . . ?
N1A C2A C3A 122.2(3) . . ?
N1A C2A H2A 118.9 . . ?
C3A C2A H2A 118.9 . . ?
C6B C5B C4B 120.4(3) . . ?
C6B C5B H5B 119.8 . . ?
C4B C5B H5B 119.8 . . ?
N2A C7A H7A1 109.5 . . ?
N2A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
N2A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
N2B C7B H7B1 109.5 . . ?
N2B C7B H7B2 109.5 . . ?
H7B1 C7B H7B2 109.5 . . ?
N2B C7B H7B3 109.5 . . ?
H7B1 C7B H7B3 109.5 . . ?
H7B2 C7B H7B3 109.5 . . ?
N2B C8B H8B1 109.5 . . ?
N2B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
N2B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C6A C5A C4A 120.5(3) . . ?
C6A C5A H5A 119.7 . . ?
C4A C5A H5A 119.7 . . ?
N1B C6B C5B 121.3(3) . . ?
N1B C6B H6B 119.4 . . ?
C5B C6B H6B 119.4 . . ?

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
C5B C4B N2B C8B 1.0(5) . . . . ?
C3B C4B N2B C8B -178.6(4) . . . . ?
C5B C4B N2B C7B -177.2(3) . . . . ?
C3B C4B N2B C7B 3.2(5) . . . . ?
C5A C6A N1A C2A -1.3(5) . . . . ?
C8A N2A C4A C5A 8.4(5) . . . . ?
C7A N2A C4A C5A -176.9(3) . . . . ?
C8A N2A C4A C3A -171.4(3) . . . . ?
C7A N2A C4A C3A 3.3(5) . . . . ?
C2A C3A C4A N2A 179.1(3) . . . . ?
C2A C3A C4A C5A -0.8(4) . . . . ?
C6B N1B C2B C3B -0.7(5) . . . . ?
N1B C2B C3B C4B 1.2(5) . . . . ?
N2B C4B C3B C2B 179.1(3) . . . . ?
C5B C4B C3B C2B -0.5(5) . . . . ?
C6A N1A C2A C3A 1.8(5) . . . . ?
C4A C3A C2A N1A -0.8(5) . . . . ?
N2B C4B C5B C6B 179.8(3) . . . . ?
C3B C4B C5B C6B -0.6(5) . . . . ?
N1A C6A C5A C4A -0.3(5) . . . . ?
N2A C4A C5A C6A -178.5(3) . . . . ?
C3A C4A C5A C6A 1.3(5) . . . . ?
C2B N1B C6B C5B -0.5(5) . . . . ?
C4B C5B C6B N1B 1.1(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
_geom_hbond_publ_flag
C3A H3A I8 0.95 3.08 3.965(3) 155.8 6_557 yes
C6A H6A I6 0.95 3.06 3.723(3) 128.6 5_666 yes
C6A H6A I8 0.95 3.29 3.827(3) 118.0 . yes
C8A H8A2 I1 0.98 3.26 4.110(4) 146.6 2_564 yes
N1A H1A I3 0.88 2.92 3.702(3) 148.2 . yes
N1A H1A I6 0.88 3.32 3.734(3) 111.6 . yes
N1B H1B I4 0.88 2.74 3.528(3) 149.2 . yes
C2B H2B I6 0.95 3.12 3.853(3) 135.5 5_666 yes
C2A H2A I2 0.95 3.08 4.002(3) 164.2 6_557 yes
C5B H5B I8 0.95 3.22 4.090(3) 152.3 6_657 yes
C7B H7B1 I2 0.98 3.26 3.774(4) 114.2 2_664 yes
C7B H7B2 I5 0.98 3.33 3.966(4) 124.7 2_665 yes
C7B H7B3 I7 0.98 3.22 3.796(5) 119.5 5_666 yes
C5A H5A I6 0.95 3.30 3.841(3) 118.3 5_666 yes

_refine_diff_density_max         2.147
_refine_diff_density_min         -1.772
_refine_diff_density_rms         0.177

