# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_NK693_pl
_database_code_depnum_ccdc_archive 'CCDC 2141780'
loop_
_audit_author_name
_audit_author_address
'Pavel Abramov'
;Nikolaev Institute of Inorganic Chemistry SB RAS
Russia
;
_audit_update_record             
;
2022-01-13 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT972_NK693_pl            
;
PROBLEM: Check Calcd Resid. Dens.  1.49Ang From C12            -3.88 eA-3
RESPONSE: The complecated disordering of TMA cations has been modelled using restraints to keep right geometry of the cations.
;
_vrf_PLAT971_NK693_pl            
;
PROBLEM: Check Calcd Resid. Dens.  0.86Ang From C13             3.38 eA-3
RESPONSE: The complecated disordering of TMA cations has been modelled using restraints to keep right geometry of the cations.
;
# Added during the CSD deposition process: Thursday 13 January 2022 10:01 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H36 Bi2 Cl11 N3'
_chemical_formula_weight         1030.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'

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

_cell_length_a                   9.1792(3)
_cell_length_b                   9.1792(3)
_cell_length_c                   21.9776(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1603.69(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.5622
_cell_measurement_theta_max      29.5495

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.134
_exptl_crystal_F_000             964
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    11.882
_shelx_estimated_absorpt_T_min   0.330
_shelx_estimated_absorpt_T_max   0.648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5241
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            16530
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.1101
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.562
_diffrn_reflns_theta_max         25.661
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             621
_reflns_number_gt                615
_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       'APEX3 (Bruker-AXS, 2016)'
_computing_cell_refinement       'SAINT (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT (Bruker-AXS, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+50.5902P] 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         621
_refine_ls_number_parameters     50
_refine_ls_number_restraints     94
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1409
_refine_ls_goodness_of_fit_ref   1.449
_refine_ls_restrained_S_all      1.343
_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 0.333333 0.666667 0.16278(6) 0.0339(4) Uani 1 6 d S T P . .
Cl1 Cl 0.0519(8) 0.1038(16) 0.0260(5) 0.035(3) Uani 0.3334 2 d S T P . .
Cl3 Cl 0.0600(10) 0.5300(5) 0.250000 0.078(3) Uani 1 4 d S T P . .
Cl2A Cl 0.189(2) 0.379(5) 0.1108(15) 0.053(9) Uiso 0.2 2 d S . P . .
Cl2B Cl 0.2449(12) 0.4071(12) 0.0959(4) 0.042(2) Uiso 0.4 1 d . . P . .
N1 N -0.333333 0.333333 0.0883(9) 0.036(5) Uani 1 6 d DS T P . .
C11 C -0.184(3) 0.318(4) 0.068(3) 0.036(5) Uani 0.1667 1 d D . P A -1
H11A H -0.084261 0.395399 0.091645 0.054 Uiso 0.1667 1 calc R U P A -1
H11B H -0.207747 0.202307 0.074391 0.054 Uiso 0.1667 1 calc R U P A -1
H11C H -0.162104 0.346122 0.024632 0.054 Uiso 0.1667 1 calc R U P A -1
C12 C -0.487(4) 0.213(4) 0.052(2) 0.036(5) Uani 0.1667 1 d D . P A -1
H12A H -0.465565 0.241507 0.008231 0.054 Uiso 0.1667 1 calc R U P A -1
H12B H -0.511326 0.097758 0.058029 0.054 Uiso 0.1667 1 calc R U P A -1
H12C H -0.583793 0.223412 0.064623 0.054 Uiso 0.1667 1 calc R U P A -1
C13 C -0.367(7) 0.290(5) 0.1553(13) 0.036(5) Uani 0.1667 1 d D . P A -1
H13A H -0.267216 0.367402 0.178997 0.054 Uiso 0.1667 1 calc R U P A -1
H13B H -0.463245 0.299926 0.168409 0.054 Uiso 0.1667 1 calc R U P A -1
H13C H -0.390778 0.174271 0.161815 0.054 Uiso 0.1667 1 calc R U P A -1
C14 C -0.296(4) 0.512(3) 0.078(3) 0.036(5) Uani 0.1667 1 d D . P A -1
H14A H -0.196477 0.589843 0.101933 0.054 Uiso 0.1667 1 calc R U P A -1
H14B H -0.274252 0.540540 0.034910 0.054 Uiso 0.1667 1 calc R U P A -1
H14C H -0.392478 0.522433 0.091304 0.054 Uiso 0.1667 1 calc R U P A -1
N2 N 0.000000 0.000000 0.250000 0.038(8) Uani 1 12 d DS T P . .
C21 C -0.080(10) -0.137(7) 0.298(2) 0.038(8) Uani 0.0833 1 d D . P B -1
H21A H -0.065004 -0.231680 0.286533 0.057 Uiso 0.0833 1 calc R U P B -1
H21B H -0.025792 -0.091930 0.337357 0.057 Uiso 0.0833 1 calc R U P B -1
H21C H -0.200097 -0.174675 0.300971 0.057 Uiso 0.0833 1 calc R U P B -1
C22 C -0.023(8) 0.147(5) 0.268(3) 0.038(8) Uani 0.0833 1 d D . P B -1
H22A H -0.143140 0.109137 0.270702 0.057 Uiso 0.0833 1 calc R U P B -1
H22B H 0.031243 0.191961 0.307040 0.057 Uiso 0.0833 1 calc R U P B -1
H22C H 0.028628 0.235321 0.236660 0.057 Uiso 0.0833 1 calc R U P B -1
C23 C -0.084(9) -0.069(9) 0.1890(19) 0.038(8) Uani 0.0833 1 d D . P B -1
H23A H -0.069004 -0.164440 0.177584 0.057 Uiso 0.0833 1 calc R U P B -1
H23B H -0.204046 -0.107375 0.192033 0.057 Uiso 0.0833 1 calc R U P B -1
H23C H -0.032255 0.018813 0.158004 0.057 Uiso 0.0833 1 calc R U P B -1
C24 C 0.186(3) 0.059(8) 0.245(4) 0.038(8) Uani 0.0833 1 d D . P B -1
H24A H 0.200936 -0.036342 0.233877 0.057 Uiso 0.0833 1 calc R U P B -1
H24B H 0.237734 0.146917 0.214281 0.057 Uiso 0.0833 1 calc R U P B -1
H24C H 0.240349 0.103557 0.284661 0.057 Uiso 0.0833 1 calc R U P B -1


_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 Cl2A 2.56(3) 5_565 ?
Bi1 Cl2A 2.56(3) . ?
Bi1 Cl2A 2.56(3) 3_665 ?
Bi1 Cl2B 2.562(9) . ?
Bi1 Cl2B 2.562(9) 5_565 ?
Bi1 Cl2B 2.562(9) 24_565 ?
Bi1 Cl2B 2.562(9) 20 ?
Bi1 Cl2B 2.562(9) 3_665 ?
Bi1 Cl2B 2.562(9) 22_665 ?
Bi1 Cl3 2.897(6) 3_665 ?
Bi1 Cl3 2.897(6) . ?
Bi1 Cl3 2.898(6) 14_566 ?
Cl1 Cl1 1.41(2) 17 ?
Cl1 Cl1 1.41(2) 15 ?
Cl1 Cl1 1.43(2) 3 ?
Cl1 Cl1 1.43(2) 5 ?
Cl1 Cl1 2.01(2) 13 ?
Cl2A Cl2B 0.55(3) . ?
Cl2A Cl2B 0.55(3) 20 ?
Cl2B Cl2B 0.759(19) 20 ?
N1 C12 1.52(2) . ?
N1 C13 1.52(2) . ?
N1 C14 1.52(2) . ?
N1 C11 1.52(2) . ?
N2 C22 1.52(2) . ?
N2 C24 1.52(2) . ?
N2 C21 1.52(2) . ?
N2 C23 1.52(2) . ?

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
Cl2A Bi1 Cl2A 101.6(10) 5_565 . ?
Cl2A Bi1 Cl2A 101.6(10) 5_565 3_665 ?
Cl2A Bi1 Cl2A 101.6(10) . 3_665 ?
Cl2A Bi1 Cl2B 102.7(6) 5_565 . ?
Cl2A Bi1 Cl2B 12.3(6) . . ?
Cl2A Bi1 Cl2B 89.4(6) 3_665 . ?
Cl2A Bi1 Cl2B 12.3(6) 5_565 5_565 ?
Cl2A Bi1 Cl2B 89.4(6) . 5_565 ?
Cl2A Bi1 Cl2B 102.7(6) 3_665 5_565 ?
Cl2B Bi1 Cl2B 90.4(3) . 5_565 ?
Cl2A Bi1 Cl2B 12.3(6) 5_565 24_565 ?
Cl2A Bi1 Cl2B 102.7(6) . 24_565 ?
Cl2A Bi1 Cl2B 89.4(6) 3_665 24_565 ?
Cl2B Bi1 Cl2B 101.0(3) . 24_565 ?
Cl2B Bi1 Cl2B 17.0(4) 5_565 24_565 ?
Cl2A Bi1 Cl2B 89.4(6) 5_565 20 ?
Cl2A Bi1 Cl2B 12.3(6) . 20 ?
Cl2A Bi1 Cl2B 102.7(6) 3_665 20 ?
Cl2B Bi1 Cl2B 17.0(4) . 20 ?
Cl2B Bi1 Cl2B 77.2(5) 5_565 20 ?
Cl2B Bi1 Cl2B 90.4(3) 24_565 20 ?
Cl2A Bi1 Cl2B 89.4(6) 5_565 3_665 ?
Cl2A Bi1 Cl2B 102.7(6) . 3_665 ?
Cl2A Bi1 Cl2B 12.3(6) 3_665 3_665 ?
Cl2B Bi1 Cl2B 90.4(3) . 3_665 ?
Cl2B Bi1 Cl2B 90.4(3) 5_565 3_665 ?
Cl2B Bi1 Cl2B 77.2(5) 24_565 3_665 ?
Cl2B Bi1 Cl2B 101.0(3) 20 3_665 ?
Cl2A Bi1 Cl2B 102.7(6) 5_565 22_665 ?
Cl2A Bi1 Cl2B 89.4(6) . 22_665 ?
Cl2A Bi1 Cl2B 12.3(6) 3_665 22_665 ?
Cl2B Bi1 Cl2B 77.2(5) . 22_665 ?
Cl2B Bi1 Cl2B 101.0(3) 5_565 22_665 ?
Cl2B Bi1 Cl2B 90.4(3) 24_565 22_665 ?
Cl2B Bi1 Cl2B 90.4(3) 20 22_665 ?
Cl2B Bi1 Cl2B 17.0(4) 3_665 22_665 ?
Cl2A Bi1 Cl3 165.1(8) 5_565 3_665 ?
Cl2A Bi1 Cl3 87.7(6) . 3_665 ?
Cl2A Bi1 Cl3 87.7(6) 3_665 3_665 ?
Cl2B Bi1 Cl3 88.93(19) . 3_665 ?
Cl2B Bi1 Cl3 169.62(19) 5_565 3_665 ?
Cl2B Bi1 Cl3 169.62(19) 24_565 3_665 ?
Cl2B Bi1 Cl3 100.0(2) 20 3_665 ?
Cl2B Bi1 Cl3 100.0(2) 3_665 3_665 ?
Cl2B Bi1 Cl3 88.93(19) 22_665 3_665 ?
Cl2A Bi1 Cl3 87.7(6) 5_565 . ?
Cl2A Bi1 Cl3 87.7(6) . . ?
Cl2A Bi1 Cl3 165.1(8) 3_665 . ?
Cl2B Bi1 Cl3 100.0(2) . . ?
Cl2B Bi1 Cl3 88.93(19) 5_565 . ?
Cl2B Bi1 Cl3 100.0(2) 24_565 . ?
Cl2B Bi1 Cl3 88.93(19) 20 . ?
Cl2B Bi1 Cl3 169.62(19) 3_665 . ?
Cl2B Bi1 Cl3 169.62(19) 22_665 . ?
Cl3 Bi1 Cl3 80.99(17) 3_665 . ?
Cl2A Bi1 Cl3 87.7(6) 5_565 14_566 ?
Cl2A Bi1 Cl3 165.1(8) . 14_566 ?
Cl2A Bi1 Cl3 87.7(6) 3_665 14_566 ?
Cl2B Bi1 Cl3 169.62(19) . 14_566 ?
Cl2B Bi1 Cl3 100.0(2) 5_565 14_566 ?
Cl2B Bi1 Cl3 88.93(19) 24_565 14_566 ?
Cl2B Bi1 Cl3 169.62(19) 20 14_566 ?
Cl2B Bi1 Cl3 88.93(19) 3_665 14_566 ?
Cl2B Bi1 Cl3 100.0(2) 22_665 14_566 ?
Cl3 Bi1 Cl3 81.00(17) 3_665 14_566 ?
Cl3 Bi1 Cl3 81.00(17) . 14_566 ?
Cl1 Cl1 Cl1 60.9(12) 17 15 ?
Cl1 Cl1 Cl1 59.6(6) 17 3 ?
Cl1 Cl1 Cl1 89.996(1) 15 3 ?
Cl1 Cl1 Cl1 89.996(1) 17 5 ?
Cl1 Cl1 Cl1 59.6(6) 15 5 ?
Cl1 Cl1 Cl1 59.999(1) 3 5 ?
Cl1 Cl1 Cl1 45.4(5) 17 13 ?
Cl1 Cl1 Cl1 45.4(5) 15 13 ?
Cl1 Cl1 Cl1 44.6(5) 3 13 ?
Cl1 Cl1 Cl1 44.6(5) 5 13 ?
Bi1 Cl3 Bi1 82.8(2) 14_566 . ?
Cl2B Cl2A Cl2B 87(6) . 20 ?
Cl2B Cl2A Bi1 84(4) . . ?
Cl2B Cl2A Bi1 84(4) 20 . ?
Cl2A Cl2B Cl2B 46(3) . 20 ?
Cl2A Cl2B Bi1 84(4) . . ?
Cl2B Cl2B Bi1 81.5(2) 20 . ?
C12 N1 C13 109.5(6) . . ?
C12 N1 C14 109.5(6) . . ?
C13 N1 C14 109.4(6) . . ?
C12 N1 C11 109.5(6) . . ?
C13 N1 C11 109.5(6) . . ?
C14 N1 C11 109.4(6) . . ?
C22 N2 C24 109.5(6) . . ?
C22 N2 C21 109.5(6) . . ?
C24 N2 C21 109.5(6) . . ?
C22 N2 C23 109.5(6) . . ?
C24 N2 C23 109.5(6) . . ?
C21 N2 C23 109.4(6) . . ?

_refine_diff_density_max         1.758
_refine_diff_density_min         -2.463
_refine_diff_density_rms         0.189


_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_detector                 PIXEL

