# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_PhaseI
_database_code_depnum_ccdc_archive 'CCDC 2105339'
loop_
_audit_author_name
_audit_author_address
'Anna Gagor'
;ILT SR PAS Wroclaw Poland
Poland
;
_audit_update_record             
;
2021-08-25 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H30 I18 N12 Sb4'
_chemical_formula_weight         3185.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'x+1/2, -y+1/2, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   8.7193(6)
_cell_length_b                   17.2789(10)
_cell_length_c                   22.2537(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3352.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    285.00(10)
_cell_measurement_reflns_used    2605
_cell_measurement_theta_min      3.1950
_cell_measurement_theta_max      27.3330

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.156
_exptl_crystal_F_000             2760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    9.907
_exptl_absorpt_correction_T_min  0.16038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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 3.055
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      285.00(10)
_diffrn_ambient_environment      air
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            8952
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.985
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.678
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1741
_reflns_number_gt                1127
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1100P)²+100.0000P] 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         1741
_refine_ls_number_parameters     40
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0780
_refine_ls_wR_factor_ref         0.2514
_refine_ls_wR_factor_gt          0.2111
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.282
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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
Sb1 Sb 0.000000 0.33757(9) 0.34394(8) 0.0885(6) Uani 1 2 d S T P . .
I2 I 0.000000 0.47852(15) 0.250000 0.1120(10) Uani 1 4 d S T P . .
I3 I 0.24236(17) 0.40706(9) 0.41591(7) 0.1146(7) Uani 1 1 d . . . . .
I4 I 0.2443(2) 0.26887(11) 0.250000 0.1033(7) Uani 1 2 d S T P . .
I5 I 0.000000 0.19549(12) 0.41435(9) 0.1340(10) Uani 1 2 d S T P . .
N1 N 0.000000 0.7222(19) 0.4367(15) 0.326(16) Uiso 1 2 d DGS . P . .
H1 H 0.001909 0.762687 0.459167 0.391 Uiso 1 2 calc R U P . .
C2 C 0.0014(9) 0.7182(18) 0.3764(15) 0.326(16) Uiso 1 2 d DG . P . .
H2 H 0.004731 0.759241 0.349389 0.391 Uiso 0.5 2 calc R U P . .
C3 C -0.0030(7) 0.6410(18) 0.3631(14) 0.326(16) Uiso 0.5 2 d DG . P . .
H3 H -0.013447 0.623467 0.323781 0.391 Uiso 0.5 1 calc R U P . .
C4 C 0.0085(14) 0.5911(18) 0.4101(13) 0.326(16) Uiso 0.5 2 d DG . P . .
H4 H 0.021327 0.537706 0.412028 0.391 Uiso 0.5 1 calc R U P . .
N5 N -0.0052(12) 0.6465(19) 0.4537(14) 0.326(16) Uiso 0.5 2 d DG . P . .
H5 H -0.016782 0.633877 0.490824 0.391 Uiso 0.5 1 calc R U P . .
C6 C 0.4693(17) 0.5770(17) 0.2514(4) 0.236(17) Uiso 0.5 2 d DG . P . .
H6 H 0.432660 0.627405 0.254718 0.283 Uiso 0.25 1 calc R U P . .
C7 C 0.465(2) 0.5361(18) 0.2031(3) 0.236(17) Uiso 0.5 1 d DG . P . .
H7 H 0.448957 0.554615 0.164372 0.283 Uiso 0.5 1 calc R U P . .
N8 N 0.490(2) 0.4578(18) 0.2195(2) 0.236(17) Uiso 0.5 2 d DG . P . .
H8 H 0.492042 0.418342 0.195903 0.283 Uiso 0.5 2 calc R U P . .


_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
Sb1 I3 2.9107(18) . ?
Sb1 I3 2.9107(18) 12 ?
Sb1 I5 2.912(3) . ?
Sb1 I2 3.210(3) . ?
Sb1 I4 3.2119(19) 3 ?
Sb1 I4 3.2119(19) . ?
N1 C2 1.345(2) . ?
N1 N5 1.362(2) . ?
N1 H1 0.8600 . ?
C2 C3 1.366(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(2) . ?
C3 H3 0.9300 . ?
C3 H3 0.937(3) 12 ?
C4 N5 1.368(2) . ?
C4 H4 0.9300 . ?
C4 H4 0.959(10) 12 ?
N5 H5 0.8600 . ?
N5 H5 0.875(8) 12 ?
C6 C7 1.2870(19) . ?
C6 C7 1.361(8) 3_655 ?
C6 H6 0.9300 . ?
C6 H6 0.937(4) 10_556 ?
C7 N8 1.419(2) . ?
C7 H7 0.9300 . ?
N8 N8 1.370(8) 3_655 ?
N8 H8 0.8600 . ?

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 Sb1 I3 93.11(8) . 12 ?
I3 Sb1 I5 92.96(6) . . ?
I3 Sb1 I5 92.96(6) 12 . ?
I3 Sb1 I2 92.60(5) . . ?
I3 Sb1 I2 92.60(5) 12 . ?
I5 Sb1 I2 171.91(8) . . ?
I3 Sb1 I4 172.77(7) . 3 ?
I3 Sb1 I4 91.67(5) 12 3 ?
I5 Sb1 I4 92.21(6) . 3 ?
I2 Sb1 I4 81.75(5) . 3 ?
I3 Sb1 I4 91.67(5) . . ?
I3 Sb1 I4 172.77(7) 12 . ?
I5 Sb1 I4 92.21(6) . . ?
I2 Sb1 I4 81.75(5) . . ?
I4 Sb1 I4 83.08(7) 3 . ?
Sb1 I2 Sb1 81.28(8) . 10_556 ?
Sb1 I4 Sb1 81.22(7) . 10_556 ?


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
N1 H1 I5 0.86 2.91 3.61(3) 139.9 9_566 yes
N5 H5 I3 0.86 2.95 3.68(3) 144.7 9_566 yes


_refine_diff_density_max         1.148
_refine_diff_density_min         -1.477
_refine_diff_density_rms         0.238

####################################################################### 
# 
# 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_PhaseI_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2105341'
loop_
_audit_author_name
_audit_author_address
'Anna Gagor'
;ILT SR PAS Wroclaw Poland
Poland
;
_audit_update_record             
;
2021-08-25 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H30 Bi4 I18 N12'
_chemical_formula_weight         3534.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y+1/2, -z-1/2'
'x+1/2, -y+1/2, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   8.7327(6)
_cell_length_b                   17.1518(10)
_cell_length_c                   22.4125(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3357.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    281(1)
_cell_measurement_reflns_used    2796
_cell_measurement_theta_min      3.0140
_cell_measurement_theta_max      24.7840

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.497
_exptl_crystal_F_000             3016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    18.755
_exptl_absorpt_correction_T_min  0.09784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.388
_oxdiff_exptl_absorpt_empirical_full_max 4.245
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      281(1)
_diffrn_ambient_environment      air
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            9694
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.991
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.681
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1750
_reflns_number_gt                1166
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.6000P] 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       0.00027(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1750
_refine_ls_number_parameters     55
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.2158
_refine_ls_wR_factor_gt          0.1926
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_restrained_S_all      1.289
_refine_ls_shift/su_max          0.003
_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 0.000000 0.33808(5) 0.34445(4) 0.0818(5) Uani 1 2 d S T P . .
I2 I 0.000000 0.48028(13) 0.250000 0.1006(8) Uani 1 4 d S T P . .
I3 I 0.24731(14) 0.40990(8) 0.41738(6) 0.1048(6) Uani 1 1 d . . . . .
I4 I 0.24419(18) 0.26798(11) 0.250000 0.0944(6) Uani 1 2 d S T P . .
I5 I 0.000000 0.19140(11) 0.41547(8) 0.1255(8) Uani 1 2 d S T P . .
N1 N 0.000000 0.7243(14) 0.4371(16) 0.236(13) Uani 1 2 d DS T P . .
H1 H 0.000000 0.765118 0.459398 0.283 Uiso 1 2 calc R U P . .
C2 C 0.000000 0.7245(17) 0.3759(16) 0.236(13) Uani 1 2 d DS T P . .
H2 H 0.000000 0.768131 0.351263 0.283 Uiso 1 2 calc R U P . .
C3 C 0.000000 0.648(2) 0.3582(11) 0.236(13) Uani 1 2 d DS T P . .
H3 H 0.000000 0.630771 0.318860 0.283 Uiso 1 2 calc R U P . .
C4 C 0.000000 0.6020(12) 0.4075(15) 0.236(13) Uani 1 2 d DS T P . .
H4 H 0.000000 0.547741 0.407601 0.283 Uiso 1 2 calc R U P . .
N5 N 0.000000 0.6488(18) 0.4570(11) 0.236(13) Uani 1 2 d DS T P . .
H5 H 0.000000 0.633683 0.493622 0.283 Uiso 1 2 calc R U P . .
C6 C 0.486(3) 0.5773(19) 0.250000 0.215(14) Uiso 0.5 2 d DS . P . .
H6 H 0.470551 0.630905 0.250675 0.258 Uiso 0.25 2 calc R U P . .
C7 C 0.479(4) 0.5309(19) 0.2007(4) 0.215(14) Uiso 0.5 1 d D . P . .
H7 H 0.461954 0.547196 0.161615 0.258 Uiso 0.5 1 calc R U P . .
N8 N 0.500000 0.4555(19) 0.2196(2) 0.215(14) Uiso 1 2 d DS . P . .
H8 H 0.511425 0.415380 0.197011 0.258 Uiso 0.5 2 calc R U P . .


_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 2.9755(14) . ?
Bi1 I3 2.9755(13) 12 ?
Bi1 I5 2.977(2) . ?
Bi1 I2 3.2295(19) . ?
Bi1 I4 3.2364(13) . ?
Bi1 I4 3.2364(13) 3 ?


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 93.07(6) . 12 ?
I3 Bi1 I5 93.22(4) . . ?
I3 Bi1 I5 93.22(4) 12 . ?
I3 Bi1 I2 92.72(4) . . ?
I3 Bi1 I2 92.72(4) 12 . ?
I5 Bi1 I2 171.37(6) . . ?
I3 Bi1 I4 92.00(4) . . ?
I3 Bi1 I4 172.47(4) 12 . ?
I5 Bi1 I4 92.05(4) . . ?
I2 Bi1 I4 81.48(4) . . ?
I3 Bi1 I4 172.47(4) . 3 ?
I3 Bi1 I4 92.00(4) 12 3 ?
I5 Bi1 I4 92.05(4) . 3 ?
I2 Bi1 I4 81.48(4) . 3 ?
I4 Bi1 I4 82.43(5) . 3 ?
Bi1 I2 Bi1 81.91(6) 10_556 . ?
Bi1 I4 Bi1 81.70(4) 10_556 . ?



_refine_diff_density_max         1.122
_refine_diff_density_min         -1.588
_refine_diff_density_rms         0.225

####################################################################### 
# 
# 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_PhaseII
_database_code_depnum_ccdc_archive 'CCDC 2105340'
loop_
_audit_author_name
_audit_author_address
'Anna Gagor'
;ILT SR PAS Wroclaw Poland
Poland
;
_audit_update_record             
;
2021-08-25 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H15 Bi2 I9 N6'
_chemical_formula_weight         1767.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.874(2)
_cell_length_b                   14.249(3)
_cell_length_c                   22.430(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.211(15)
_cell_angle_gamma                90
_cell_volume                     3155.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    109.8(3)
_cell_measurement_reflns_used    2399
_cell_measurement_theta_min      2.7060
_cell_measurement_theta_max      26.6240

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.720
_exptl_crystal_F_000             3016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    19.951
_exptl_absorpt_correction_T_min  0.59589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.493
_oxdiff_exptl_absorpt_empirical_full_max 2.402
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      109.8(3)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.6249
_diffrn_reflns_number            17109
_diffrn_reflns_av_unetI/netI     0.4969
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.510
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.000
_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             17109
_reflns_number_gt                5314
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)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_number_reflns         17109
_refine_ls_number_parameters     164
_refine_ls_number_restraints     90
_refine_ls_R_factor_all          0.2316
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.1805
_refine_ls_wR_factor_gt          0.1529
_refine_ls_goodness_of_fit_ref   0.782
_refine_ls_restrained_S_all      0.780
_refine_ls_shift/su_max          0.000
_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 0.49300(16) 0.82766(12) 0.15667(8) 0.0244(4) Uani 1 1 d . . . . .
Bi2 Bi 0.49332(15) 0.82749(11) 0.34334(8) 0.0231(4) Uani 1 1 d . . . . .
I1 I 0.3117(2) 0.71608(17) 0.24997(14) 0.0268(7) Uani 1 1 d . . . . .
I2 I 0.7255(3) 0.76260(18) 0.25035(14) 0.0290(7) Uani 1 1 d . . . . .
I3 I 0.4687(3) 0.99567(17) 0.24992(16) 0.0314(7) Uani 1 1 d . . . . .
I4 I 0.6900(3) 0.94244(19) 0.41434(13) 0.0290(7) Uani 1 1 d . . . . .
I5 I 0.2610(3) 0.89504(19) 0.41639(13) 0.0301(8) Uani 1 1 d . . . . .
I6 I 0.5230(3) 0.6594(2) 0.42013(14) 0.0299(8) Uani 1 1 d . . . . .
I7 I 0.5225(3) 0.6593(2) 0.07985(15) 0.0320(8) Uani 1 1 d . . . . .
I8 I 0.2610(3) 0.89497(19) 0.08346(13) 0.0297(8) Uani 1 1 d . . . . .
I9 I 0.6900(3) 0.94232(19) 0.08563(13) 0.0292(7) Uani 1 1 d . . . . .
N1 N 0.581(3) 0.859(2) -0.0521(18) 0.042(5) Uani 1 1 d . U . . .
H1 H 0.627324 0.885599 -0.024440 0.051 Uiso 1 1 calc R U . . .
N2 N 0.467(3) 0.817(2) -0.0463(19) 0.042(5) Uani 1 1 d . U . . .
H2 H 0.424317 0.809222 -0.013425 0.051 Uiso 1 1 calc R U . . .
C3 C 0.425(5) 0.785(3) -0.102(2) 0.042(5) Uani 1 1 d . U . . .
H3 H 0.343581 0.754997 -0.111029 0.051 Uiso 1 1 calc R U . . .
C4 C 0.511(4) 0.805(3) -0.137(2) 0.042(5) Uani 1 1 d . U . . .
H4 H 0.509633 0.789867 -0.177164 0.051 Uiso 1 1 calc R U . . .
C5 C 0.612(4) 0.852(3) -0.109(2) 0.042(5) Uani 1 1 d . U . . .
H5 H 0.690119 0.876011 -0.126861 0.051 Uiso 1 1 calc R U . . .
N6 N 0.469(3) 0.825(2) 0.5434(19) 0.046(5) Uani 1 1 d . U . . .
H6 H 0.430263 0.823168 0.509147 0.055 Uiso 1 1 calc R U . . .
N7 N 0.581(3) 0.862(2) 0.5540(18) 0.046(5) Uani 1 1 d . U . . .
H7 H 0.630659 0.890639 0.528291 0.055 Uiso 1 1 calc R U . . .
C8 C 0.612(4) 0.851(3) 0.613(2) 0.046(5) Uani 1 1 d . U . . .
H8 H 0.689960 0.871540 0.632514 0.055 Uiso 1 1 calc R U . . .
C9 C 0.510(4) 0.804(3) 0.636(2) 0.046(5) Uani 1 1 d . U . . .
H9 H 0.506499 0.787399 0.676139 0.055 Uiso 1 1 calc R U . . .
C10 C 0.415(5) 0.784(3) 0.598(2) 0.046(5) Uani 1 1 d . U . . .
H10 H 0.334347 0.752592 0.604458 0.055 Uiso 1 1 calc R U . . .
N11 N 0.605(3) 0.509(3) 0.2208(18) 0.048(5) Uani 1 1 d . U . . .
H11 H 0.661218 0.537352 0.197657 0.058 Uiso 1 1 calc R U . . .
N12 N 0.617(3) 0.510(3) 0.2816(18) 0.048(5) Uani 1 1 d . U . . .
H12 H 0.680553 0.532295 0.303573 0.058 Uiso 1 1 calc R U . . .
C13 C 0.505(4) 0.466(3) 0.297(3) 0.048(5) Uani 1 1 d . U . . .
H13 H 0.479627 0.453940 0.336575 0.058 Uiso 1 1 calc R U . . .
C14 C 0.436(5) 0.442(3) 0.251(2) 0.048(5) Uani 1 1 d . U . . .
H14 H 0.350593 0.414671 0.252097 0.058 Uiso 1 1 calc R U . . .
C15 C 0.503(4) 0.463(3) 0.201(3) 0.048(5) Uani 1 1 d . U . . .
H15 H 0.480354 0.447886 0.162312 0.058 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 I7 2.968(3) . ?
Bi1 I8 2.972(3) . ?
Bi1 I9 3.002(3) . ?
Bi1 I1 3.184(3) . ?
Bi1 I3 3.189(3) . ?
Bi1 I2 3.242(3) . ?
Bi2 I6 2.965(3) . ?
Bi2 I5 2.984(3) . ?
Bi2 I4 2.995(3) . ?
Bi2 I1 3.177(3) . ?
Bi2 I3 3.192(3) . ?
Bi2 I2 3.240(3) . ?
N1 N2 1.28(4) . ?
N1 C5 1.32(6) . ?
N1 H1 0.8600 . ?
N2 C3 1.40(6) . ?
N2 H2 0.8600 . ?
C3 C4 1.19(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.36(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
N6 N7 1.25(4) . ?
N6 C10 1.46(6) . ?
N6 H6 0.8600 . ?
N7 C8 1.36(6) . ?
N7 H7 0.8600 . ?
C8 C9 1.32(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.29(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
N11 C15 1.28(5) . ?
N11 N12 1.37(5) . ?
N11 H11 0.8600 . ?
N12 C13 1.32(5) . ?
N12 H12 0.8600 . ?
C13 C14 1.29(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.33(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I7 Bi1 I8 90.98(9) . . ?
I7 Bi1 I9 93.82(9) . . ?
I8 Bi1 I9 91.75(9) . . ?
I7 Bi1 I1 91.98(9) . . ?
I8 Bi1 I1 95.18(9) . . ?
I9 Bi1 I1 170.88(10) . . ?
I7 Bi1 I3 174.41(11) . . ?
I8 Bi1 I3 93.47(9) . . ?
I9 Bi1 I3 89.43(9) . . ?
I1 Bi1 I3 84.25(9) . . ?
I7 Bi1 I2 94.27(9) . . ?
I8 Bi1 I2 173.11(10) . . ?
I9 Bi1 I2 92.35(9) . . ?
I1 Bi1 I2 80.19(8) . . ?
I3 Bi1 I2 81.04(8) . . ?
I6 Bi2 I5 90.93(9) . . ?
I6 Bi2 I4 94.04(9) . . ?
I5 Bi2 I4 91.71(9) . . ?
I6 Bi2 I1 91.92(9) . . ?
I5 Bi2 I1 95.16(9) . . ?
I4 Bi2 I1 170.82(10) . . ?
I6 Bi2 I3 174.41(11) . . ?
I5 Bi2 I3 93.52(9) . . ?
I4 Bi2 I3 89.21(9) . . ?
I1 Bi2 I3 84.32(9) . . ?
I6 Bi2 I2 94.28(9) . . ?
I5 Bi2 I2 173.21(10) . . ?
I4 Bi2 I2 92.26(9) . . ?
I1 Bi2 I2 80.33(8) . . ?
I3 Bi2 I2 81.03(8) . . ?
Bi2 I1 Bi1 82.33(7) . . ?
Bi2 I2 Bi1 80.48(7) . . ?
Bi1 I3 Bi2 82.02(7) . . ?
N2 N1 C5 106(4) . . ?
N2 N1 H1 127.0 . . ?
C5 N1 H1 127.0 . . ?
N1 N2 C3 109(4) . . ?
N1 N2 H2 125.6 . . ?
C3 N2 H2 125.6 . . ?
C4 C3 N2 107(5) . . ?
C4 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
C3 C4 C5 110(6) . . ?
C3 C4 H4 124.8 . . ?
C5 C4 H4 124.8 . . ?
N1 C5 C4 108(4) . . ?
N1 C5 H5 126.2 . . ?
C4 C5 H5 126.2 . . ?
N7 N6 C10 109(4) . . ?
N7 N6 H6 125.3 . . ?
C10 N6 H6 125.3 . . ?
N6 N7 C8 109(4) . . ?
N6 N7 H7 125.3 . . ?
C8 N7 H7 125.3 . . ?
C9 C8 N7 106(4) . . ?
C9 C8 H8 127.1 . . ?
N7 C8 H8 127.1 . . ?
C10 C9 C8 114(5) . . ?
C10 C9 H9 123.0 . . ?
C8 C9 H9 123.0 . . ?
C9 C10 N6 102(4) . . ?
C9 C10 H10 129.2 . . ?
N6 C10 H10 129.2 . . ?
C15 N11 N12 114(4) . . ?
C15 N11 H11 123.1 . . ?
N12 N11 H11 123.1 . . ?
C13 N12 N11 101(4) . . ?
C13 N12 H12 129.3 . . ?
N11 N12 H12 129.3 . . ?
N12 C13 C14 110(5) . . ?
N12 C13 H13 124.8 . . ?
C14 C13 H13 124.8 . . ?
C13 C14 C15 111(5) . . ?
C13 C14 H14 124.6 . . ?
C15 C14 H14 124.6 . . ?
N11 C15 C14 103(5) . . ?
N11 C15 H15 128.5 . . ?
C14 C15 H15 128.5 . . ?

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
N1 H1 I9 0.86 2.67 3.48(4) 157.4 . yes
N2 H2 I7 0.86 3.14 3.65(4) 120.4 . yes
N2 H2 I8 0.86 2.97 3.73(4) 147.8 . yes
N6 H6 I5 0.86 2.85 3.65(4) 154.5 . yes
N7 H7 I4 0.86 2.73 3.51(4) 151.9 . yes
N11 H11 I4 0.86 3.21 3.77(4) 125.0 2_645 yes
N12 H12 I9 0.86 3.07 3.66(4) 127.5 2_645 yes


_refine_diff_density_max         3.082
_refine_diff_density_min         -2.180
_refine_diff_density_rms         0.566

