# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_P21
_database_code_depnum_ccdc_archive 'CCDC 2036251'
loop_
_audit_author_name
_audit_author_address
'Wei-Qiang Liao'
;Nanchang University
China
;
_audit_update_record             
;
2020-10-09 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(Bi I5), 3(C4 H14 N2)'
_chemical_formula_sum            'C12 H42 Bi3 I15 N6'
_chemical_formula_weight         2800.96

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   11.0339(9)
_cell_length_b                   8.5608(4)
_cell_length_c                   27.529(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.793(5)
_cell_angle_gamma                90
_cell_volume                     2562.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7427
_cell_measurement_theta_min      2.2523
_cell_measurement_theta_max      27.4932

_exptl_crystal_description       Block
_exptl_crystal_colour            'Dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.630
_exptl_crystal_F_000             2400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    19.327
_shelx_estimated_absorpt_T_min   0.066
_shelx_estimated_absorpt_T_max   0.068
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.003
_exptl_absorpt_correction_T_max  0.003
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18913
_diffrn_reflns_av_unetI/netI     0.1109
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.495
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             11302
_reflns_number_gt                8972
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.995

_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion 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)+(0.0077P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.002030(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.161(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         11302
_refine_ls_number_parameters     333
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.012
_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
C1 C 0.5618(13) 0.231(2) 0.0753(5) 0.076(6) Uani 1 1 d . . . . .
H1A H 0.5093 0.3194 0.0640 0.091 Uiso 1 1 d R U . . .
H1B H 0.5110 0.1520 0.0870 0.091 Uiso 1 1 d R U . . .
C5 C 0.5172(16) 0.773(2) 0.6843(5) 0.080(6) Uani 1 1 d . . . . .
H5A H 0.5874 0.8093 0.6706 0.096 Uiso 1 1 d R U . . .
H5B H 0.4802 0.8621 0.6976 0.096 Uiso 1 1 d R U . . .
N2 N 0.8674(11) 0.2908(17) -0.0384(4) 0.075(5) Uani 1 1 d . . . . .
H2A H 0.8400 0.3874 -0.0453 0.112 Uiso 1 1 calc R U . . .
H2B H 0.8942 0.2507 -0.0644 0.112 Uiso 1 1 calc R U . . .
H2C H 0.9287 0.2932 -0.0128 0.112 Uiso 1 1 calc R U . . .
C10 C 1.0368(17) 0.325(2) 0.6856(6) 0.094(5) Uani 1 1 d . U . . .
H10A H 1.0039 0.4297 0.6880 0.113 Uiso 1 1 d R U . . .
H10B H 1.1121 0.3204 0.7095 0.113 Uiso 1 1 d R U . . .
N3 N 0.5605(12) 0.6617(18) 0.7249(5) 0.083(6) Uani 1 1 d . . . . .
H3A H 0.5001 0.6435 0.7419 0.125 Uiso 1 1 calc R U . . .
H3B H 0.6246 0.7027 0.7449 0.125 Uiso 1 1 calc R U . . .
H3C H 0.5829 0.5724 0.7124 0.125 Uiso 1 1 calc R U . . .
C7 C 0.4032(16) 0.789(2) 0.5982(4) 0.072(6) Uani 1 1 d . . . . .
H7A H 0.3517 0.8770 0.6033 0.087 Uiso 1 1 d R U . . .
H7B H 0.4820 0.8309 0.5935 0.087 Uiso 1 1 d R U . . .
C2 C 0.6140(14) 0.1671(19) 0.0323(5) 0.064(6) Uani 1 1 d . . . . .
H2D H 0.5466 0.1435 0.0058 0.077 Uiso 1 1 d R U . . .
H2E H 0.6558 0.0697 0.0423 0.077 Uiso 1 1 d R U . . .
C11 C 0.9503(13) 0.221(2) 0.7027(6) 0.071(6) Uani 1 1 d . . . . .
H11A H 0.8765 0.2152 0.6780 0.085 Uiso 1 1 d R U . . .
H11B H 0.9866 0.1177 0.7059 0.085 Uiso 1 1 d R U . . .
N1 N 0.6517(13) 0.281(2) 0.1145(4) 0.101(7) Uani 1 1 d . . . . .
H1C H 0.7166 0.2177 0.1170 0.151 Uiso 1 1 calc R U . . .
H1D H 0.6211 0.2776 0.1424 0.151 Uiso 1 1 calc R U . . .
H1E H 0.6744 0.3779 0.1089 0.151 Uiso 1 1 calc R U . . .
C4 C 0.7668(12) 0.193(2) -0.0261(4) 0.054(5) Uani 1 1 d . . . . .
H4A H 0.7992 0.0937 -0.0132 0.065 Uiso 1 1 d R U . . .
H4B H 0.7072 0.1740 -0.0557 0.065 Uiso 1 1 d R U . . .
C3 C 0.7039(12) 0.276(2) 0.0122(4) 0.061(5) Uani 1 1 d . . . . .
H3D H 0.7658 0.3112 0.0393 0.074 Uiso 1 1 d R U . . .
H3E H 0.6599 0.3665 -0.0026 0.074 Uiso 1 1 d R U . . .
C6 C 0.4235(12) 0.7008(19) 0.6432(4) 0.046(4) Uani 1 1 d . . . . .
H6A H 0.4518 0.5972 0.6362 0.055 Uiso 1 1 d R U . . .
H6B H 0.3459 0.6890 0.6549 0.055 Uiso 1 1 d R U . . .
Bi1 Bi 0.43579(4) 1.23063(6) 0.80183(2) 0.03319(12) Uani 1 1 d . . . . .
Bi2 Bi 0.86750(4) 0.73057(6) 0.86541(2) 0.03191(12) Uani 1 1 d . . . . .
Bi3 Bi 0.85048(4) 0.76878(6) 0.55643(2) 0.03223(12) Uani 1 1 d . . . . .
I10 I 0.81700(9) 0.71959(14) 0.97360(3) 0.0504(3) Uani 1 1 d . . . . .
I5 I 0.37298(8) 1.22212(14) 0.90394(3) 0.0475(3) Uani 1 1 d . . . . .
I7 I 0.89134(9) 0.74413(15) 0.75712(3) 0.0514(3) Uani 1 1 d . . . . .
I8 I 1.02441(9) 1.00980(12) 0.88710(4) 0.0498(3) Uani 1 1 d . . . . .
I6 I 0.61814(9) 0.93901(13) 0.83302(4) 0.0531(3) Uani 1 1 d . . . . .
I9 I 1.06746(8) 0.50423(13) 0.88721(4) 0.0509(3) Uani 1 1 d . . . . .
I11 I 0.63856(9) 0.74537(16) 0.46282(3) 0.0587(3) Uani 1 1 d . . . . .
I14 I 1.06351(8) 0.78339(14) 0.63967(3) 0.0491(3) Uani 1 1 d . . . . .
I3 I 0.68314(9) 1.43626(13) 0.84317(4) 0.0530(3) Uani 1 1 d . . . . .
I1 I 0.29463(9) 1.52275(12) 0.77652(4) 0.0510(3) Uani 1 1 d . . . . .
I4 I 0.24904(9) 0.99983(14) 0.76432(4) 0.0556(3) Uani 1 1 d . . . . .
I2 I 0.51838(10) 1.24519(15) 0.69664(3) 0.0576(3) Uani 1 1 d . . . . .
I15 I 0.72773(9) 0.52238(13) 0.60500(4) 0.0537(3) Uani 1 1 d . . . . .
I12 I 0.72195(9) 1.03074(13) 0.59346(4) 0.0543(3) Uani 1 1 d . . . . .
I13 I 0.99646(13) 0.50626(18) 0.50296(5) 0.0746(4) Uani 1 1 d . . . . .
C12 C 0.9158(14) 0.262(3) 0.7487(5) 0.084(6) Uani 1 1 d . . . . .
H12A H 0.9899 0.2654 0.7733 0.101 Uiso 1 1 d R U . . .
H12B H 0.8828 0.3677 0.7456 0.101 Uiso 1 1 d R U . . .
N6 N 0.8304(12) 0.1670(19) 0.7665(4) 0.083(6) Uani 1 1 d . . . . .
H6C H 0.7696 0.1434 0.7420 0.124 Uiso 1 1 calc R U . . .
H6D H 0.8000 0.2172 0.7900 0.124 Uiso 1 1 calc R U . . .
H6E H 0.8672 0.0796 0.7787 0.124 Uiso 1 1 calc R U . . .
N4 N 0.3251(15) 0.8161(16) 0.5114(5) 0.101(7) Uani 1 1 d . . . . .
H4C H 0.2492 0.8542 0.5086 0.151 Uiso 1 1 calc R U . . .
H4D H 0.3317 0.7602 0.4847 0.151 Uiso 1 1 calc R U . . .
H4E H 0.3788 0.8945 0.5143 0.151 Uiso 1 1 calc R U . . .
C9 C 1.0655(9) 0.3116(15) 0.6377(5) 0.121(6) Uani 1 1 d D U . . .
H9A H 1.0959 0.4143 0.6311 0.145 Uiso 1 1 d R U . . .
H9B H 0.9905 0.2961 0.6141 0.145 Uiso 1 1 d R U . . .
C8 C 0.350(2) 0.719(3) 0.5539(5) 0.123(10) Uani 1 1 d . . . . .
H8A H 0.2736 0.6705 0.5588 0.148 Uiso 1 1 d R U . . .
H8B H 0.4045 0.6363 0.5469 0.148 Uiso 1 1 d R U . . .
N5 N 1.1655(9) 0.2092(16) 0.6274(5) 0.224(8) Uani 1 1 d D U . . .
H5C H 1.2058 0.1705 0.6556 0.336 Uiso 1 1 calc R U . . .
H5D H 1.2172 0.2640 0.6125 0.336 Uiso 1 1 calc R U . . .
H5E H 1.1340 0.1312 0.6079 0.336 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
C1 N1 1.401(18) . ?
C1 C2 1.50(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 N3 1.48(2) . ?
C5 C6 1.526(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
N2 C4 1.472(19) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C10 C9 1.41(2) . ?
C10 C11 1.44(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
C7 C8 1.39(2) . ?
C7 C6 1.436(18) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C2 C3 1.53(2) . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C11 C12 1.43(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
N1 H1C 0.8900 . ?
N1 H1D 0.8900 . ?
N1 H1E 0.8900 . ?
C4 C3 1.53(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3D 0.9700 . ?
C3 H3E 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
Bi1 I4 2.9142(12) . ?
Bi1 I1 2.9659(12) . ?
Bi1 I5 3.0081(10) . ?
Bi1 I2 3.1827(10) . ?
Bi1 I6 3.2296(11) . ?
Bi1 I3 3.2842(11) . ?
Bi2 I9 2.9210(11) . ?
Bi2 I8 2.9524(11) . ?
Bi2 I7 3.0392(10) . ?
Bi2 I10 3.1231(10) . ?
Bi2 I3 3.2306(12) 1_545 ?
Bi2 I6 3.2733(11) . ?
Bi3 I12 2.9277(12) . ?
Bi3 I15 2.9475(12) . ?
Bi3 I14 2.9933(10) . ?
Bi3 I11 3.1778(10) . ?
Bi3 I13 3.2556(15) 2_756 ?
Bi3 I13 3.2585(15) . ?
I3 Bi2 3.2307(12) 1_565 ?
I13 Bi3 3.2555(15) 2_746 ?
C12 N6 1.40(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
N6 H6C 0.8900 . ?
N6 H6D 0.8900 . ?
N6 H6E 0.8900 . ?
N4 C8 1.42(2) . ?
N4 H4C 0.8900 . ?
N4 H4D 0.8900 . ?
N4 H4E 0.8900 . ?
C9 N5 1.475(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N5 H5C 0.8900 . ?
N5 H5D 0.8900 . ?
N5 H5E 0.8900 . ?

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
N1 C1 C2 113.6(13) . . ?
N1 C1 H1A 108.6 . . ?
C2 C1 H1A 108.6 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.7 . . ?
N3 C5 C6 113.1(15) . . ?
N3 C5 H5A 109.0 . . ?
C6 C5 H5A 109.1 . . ?
N3 C5 H5B 109.0 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.8 . . ?
C4 N2 H2A 109.5 . . ?
C4 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C4 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C9 C10 C11 121.2(15) . . ?
C9 C10 H10A 106.7 . . ?
C11 C10 H10A 105.7 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 106.7 . . ?
H10A C10 H10B 106.4 . . ?
C5 N3 H3A 109.5 . . ?
C5 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C5 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C8 C7 C6 120.8(18) . . ?
C8 C7 H7A 107.0 . . ?
C6 C7 H7A 106.9 . . ?
C8 C7 H7B 107.3 . . ?
C6 C7 H7B 107.3 . . ?
H7A C7 H7B 106.9 . . ?
C1 C2 C3 114.9(14) . . ?
C1 C2 H2D 108.6 . . ?
C3 C2 H2D 108.5 . . ?
C1 C2 H2E 108.4 . . ?
C3 C2 H2E 108.6 . . ?
H2D C2 H2E 107.6 . . ?
C12 C11 C10 115.3(16) . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 108.3 . . ?
C10 C11 H11B 108.0 . . ?
H11A C11 H11B 107.5 . . ?
C1 N1 H1C 109.5 . . ?
C1 N1 H1D 109.5 . . ?
H1C N1 H1D 109.5 . . ?
C1 N1 H1E 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
N2 C4 C3 110.3(13) . . ?
N2 C4 H4A 109.6 . . ?
C3 C4 H4A 109.6 . . ?
N2 C4 H4B 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C2 C3 C4 111.6(15) . . ?
C2 C3 H3D 109.2 . . ?
C4 C3 H3D 109.3 . . ?
C2 C3 H3E 109.3 . . ?
C4 C3 H3E 109.3 . . ?
H3D C3 H3E 108.0 . . ?
C7 C6 C5 114.6(14) . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.6 . . ?
I4 Bi1 I1 100.20(3) . . ?
I4 Bi1 I5 93.06(3) . . ?
I1 Bi1 I5 92.56(3) . . ?
I4 Bi1 I2 89.93(3) . . ?
I1 Bi1 I2 88.48(3) . . ?
I5 Bi1 I2 176.62(3) . . ?
I4 Bi1 I6 86.62(3) . . ?
I1 Bi1 I6 173.11(3) . . ?
I5 Bi1 I6 87.99(3) . . ?
I2 Bi1 I6 90.59(3) . . ?
I4 Bi1 I3 169.12(4) . . ?
I1 Bi1 I3 90.10(3) . . ?
I5 Bi1 I3 89.95(3) . . ?
I2 Bi1 I3 86.82(3) . . ?
I6 Bi1 I3 83.04(3) . . ?
I9 Bi2 I8 95.68(3) . . ?
I9 Bi2 I7 92.21(3) . . ?
I8 Bi2 I7 91.25(3) . . ?
I9 Bi2 I10 92.01(3) . . ?
I8 Bi2 I10 91.44(3) . . ?
I7 Bi2 I10 174.75(3) . . ?
I9 Bi2 I3 87.18(3) . 1_545 ?
I8 Bi2 I3 176.81(3) . 1_545 ?
I7 Bi2 I3 90.04(3) . 1_545 ?
I10 Bi2 I3 87.05(3) . 1_545 ?
I9 Bi2 I6 171.16(3) . . ?
I8 Bi2 I6 92.90(3) . . ?
I7 Bi2 I6 85.47(3) . . ?
I10 Bi2 I6 89.89(3) . . ?
I3 Bi2 I6 84.29(3) 1_545 . ?
I12 Bi3 I15 95.92(3) . . ?
I12 Bi3 I14 93.74(3) . . ?
I15 Bi3 I14 92.53(3) . . ?
I12 Bi3 I11 89.85(3) . . ?
I15 Bi3 I11 89.50(3) . . ?
I14 Bi3 I11 175.67(3) . . ?
I12 Bi3 I13 91.14(4) . 2_756 ?
I15 Bi3 I13 172.94(4) . 2_756 ?
I14 Bi3 I13 87.22(3) . 2_756 ?
I11 Bi3 I13 90.30(3) . 2_756 ?
I12 Bi3 I13 172.53(4) . . ?
I15 Bi3 I13 90.68(4) . . ?
I14 Bi3 I13 89.46(3) . . ?
I11 Bi3 I13 86.69(3) . . ?
I13 Bi3 I13 82.260(12) 2_756 . ?
Bi1 I6 Bi2 161.91(4) . . ?
Bi2 I3 Bi1 160.57(4) 1_565 . ?
Bi3 I13 Bi3 174.93(6) 2_746 . ?
N6 C12 C11 117.6(17) . . ?
N6 C12 H12A 107.9 . . ?
C11 C12 H12A 107.9 . . ?
N6 C12 H12B 107.9 . . ?
C11 C12 H12B 107.8 . . ?
H12A C12 H12B 107.2 . . ?
C12 N6 H6C 109.5 . . ?
C12 N6 H6D 109.5 . . ?
H6C N6 H6D 109.5 . . ?
C12 N6 H6E 109.5 . . ?
H6C N6 H6E 109.5 . . ?
H6D N6 H6E 109.5 . . ?
C8 N4 H4C 109.5 . . ?
C8 N4 H4D 109.5 . . ?
H4C N4 H4D 109.5 . . ?
C8 N4 H4E 109.5 . . ?
H4C N4 H4E 109.5 . . ?
H4D N4 H4E 109.5 . . ?
C10 C9 N5 121.5(13) . . ?
C10 C9 H9A 103.8 . . ?
N5 C9 H9A 102.0 . . ?
C10 C9 H9B 109.6 . . ?
N5 C9 H9B 111.8 . . ?
H9A C9 H9B 106.4 . . ?
C7 C8 N4 118(2) . . ?
C7 C8 H8A 107.9 . . ?
N4 C8 H8A 108.3 . . ?
C7 C8 H8B 107.6 . . ?
N4 C8 H8B 107.7 . . ?
H8A C8 H8B 107.2 . . ?
C9 N5 H5C 109.5 . . ?
C9 N5 H5D 109.5 . . ?
H5C N5 H5D 109.5 . . ?
C9 N5 H5E 109.5 . . ?
H5C N5 H5E 109.5 . . ?
H5D N5 H5E 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
N1 C1 C2 C3 -54(2) . . . . ?
C9 C10 C11 C12 -170.9(15) . . . . ?
C1 C2 C3 C4 171.7(12) . . . . ?
N2 C4 C3 C2 -170.3(11) . . . . ?
C8 C7 C6 C5 161.1(17) . . . . ?
N3 C5 C6 C7 -164.8(14) . . . . ?
C10 C11 C12 N6 178.7(15) . . . . ?
C11 C10 C9 N5 -88.6(19) . . . . ?
C6 C7 C8 N4 175.9(16) . . . . ?

_refine_diff_density_max         1.314
_refine_diff_density_min         -1.846
_refine_diff_density_rms         0.261



####################################################################### 
# 
# 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_P21m
_database_code_depnum_ccdc_archive 'CCDC 2036252'
loop_
_audit_author_name
_audit_author_address
'Wei-Qiang Liao'
;Nanchang University
China
;
_audit_update_record             
;
2020-10-09 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(Bi I5), 3(C4 H14 N2)'
_chemical_formula_sum            'C12 H42 Bi3 I15 N6'
_chemical_formula_weight         2800.96

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

_cell_length_a                   11.180(5)
_cell_length_b                   8.575(4)
_cell_length_c                   27.548(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.185(10)
_cell_angle_gamma                90
_cell_volume                     2599(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    383(2)
_cell_measurement_reflns_used    7319
_cell_measurement_theta_min      1.5021
_cell_measurement_theta_max      27.4739

_exptl_crystal_description       Block
_exptl_crystal_colour            'Dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.579
_exptl_crystal_F_000             2400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    19.056
_shelx_estimated_absorpt_T_min   0.067
_shelx_estimated_absorpt_T_max   0.069
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.003
_exptl_absorpt_correction_T_max  0.004
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      383(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16086
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.870
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4891
_reflns_number_gt                4107
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0414P)²+69.9987P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00216(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4891
_refine_ls_number_parameters     224
_refine_ls_number_restraints     142
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_ref         0.1557
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.086
_refine_ls_shift/su_mean         0.003

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
I8' I 0.3707(2) 0.9787(3) 0.15605(11) 0.0981(5) Uani 0.5 1 d . . P . .
I8 I 0.3431(2) 1.0267(3) 0.16127(11) 0.0981(5) Uani 0.5 1 d . . P . .
Bi1 Bi 0.84725(6) 0.2500 0.55477(3) 0.04853(18) Uani 1 2 d S T P . .
Bi2 Bi 0.13939(6) 0.7500 0.13423(3) 0.0518(2) Uani 1 2 d S T P . .
Bi3 Bi 0.57102(6) 1.2500 0.19817(3) 0.0550(2) Uani 1 2 d S T P . .
C1 C 0.3180(18) 0.2500 0.5676(5) 0.213(4) Uani 1 2 d DS TU P . .
H1D H 0.2686 0.3408 0.5691 0.255 Uiso 1 1 d R U . . .
C2 C 0.406(2) 0.322(2) 0.6027(3) 0.210(3) Uani 0.5 1 d D U P . .
H2D H 0.3869 0.4311 0.6050 0.252 Uiso 0.5 1 d R U P . .
H2E H 0.4843 0.3139 0.5933 0.252 Uiso 0.5 1 d R U P . .
C3 C 0.4123(16) 0.2500 0.6485(5) 0.208(3) Uani 1 2 d DS TU P . .
H3A H 0.3707 0.1589 0.6571 0.249 Uiso 1 1 d R U . . .
C4 C 0.5236(16) 0.2500 0.6810(6) 0.205(3) Uani 1 2 d DS TU P . .
H4A H 0.5708 0.3092 0.6617 0.246 Uiso 0.5 1 d R U P . .
H4B H 0.5535 0.1449 0.6829 0.246 Uiso 0.5 1 d R U P . .
C5 C 0.0831(10) 0.2500 0.2629(3) 0.249(3) Uani 1 2 d DS TU P . .
H5D H 0.0543 0.1444 0.2621 0.299 Uiso 0.5 1 d R U P . .
H5E H 0.1542 0.2500 0.2882 0.299 Uiso 1 2 d R U P . .
C6 C 0.0263(19) 0.336(2) 0.2953(6) 0.249(3) Uani 0.5 1 d D U P . .
H6D H -0.0513 0.3397 0.2739 0.299 Uiso 0.5 1 d R U P . .
H6E H 0.0521 0.4411 0.3026 0.299 Uiso 0.5 1 d R U P . .
C7 C -0.0161(7) 0.2500 0.3312(3) 0.249(3) Uani 1 2 d DS TU P . .
H7A H 0.0520 0.2853 0.3550 0.299 Uiso 0.5 1 d R U P . .
H7B H -0.0010 0.1416 0.3260 0.299 Uiso 0.5 1 d R U P . .
C8 C -0.1002(10) 0.2500 0.3632(5) 0.250(3) Uani 1 2 d DS TU P . .
H8A H -0.0670 0.1921 0.3923 0.300 Uiso 0.5 1 d R U P . .
H8B H -0.1557 0.1792 0.3438 0.300 Uiso 0.5 1 d R U P . .
C9 C 0.7363(13) 0.7500 -0.0234(6) 0.264(6) Uani 1 2 d DS TU P . .
H9A H 0.6981 0.8407 -0.0398 0.317 Uiso 1 1 d R U . . .
C10 C 0.6925(8) 0.7500 0.0205(3) 0.263(5) Uani 1 2 d DS TU P . .
H10A H 0.6887 0.8568 0.0306 0.316 Uiso 0.5 1 d R U P . .
H10B H 0.7650 0.7061 0.0394 0.316 Uiso 0.5 1 d R U P . .
C11 C 0.5935(15) 0.676(3) 0.0346(6) 0.261(5) Uani 0.5 1 d D U P . .
H11A H 0.6182 0.5723 0.0456 0.313 Uiso 0.5 1 d R U P . .
H11B H 0.5304 0.6660 0.0062 0.313 Uiso 0.5 1 d R U P . .
C12 C 0.5506(9) 0.7500 0.0739(3) 0.257(7) Uani 1 2 d DS TU P . .
H12A H 0.4722 0.7057 0.0750 0.309 Uiso 0.5 1 d R U P . .
H12B H 0.5373 0.8569 0.0640 0.309 Uiso 0.5 1 d R U P . .
I1 I 0.64204(16) 0.2500 0.45928(7) 0.0960(6) Uani 1 2 d S T P . .
I2 I 1.0000 0.5000 0.5000 0.1090(6) Uani 1 2 d S . P . .
I3 I 1.05450(14) 0.2500 0.64043(5) 0.0745(5) Uani 1 2 d S T P . .
I4 I 0.71798(10) 0.50269(12) 0.59582(5) 0.0849(3) Uani 1 1 d . . . . .
I5 I 0.12370(17) 0.7500 0.24290(6) 0.0917(6) Uani 1 2 d S T P . .
I6 I -0.03798(10) 1.00400(13) 0.11306(5) 0.0917(4) Uani 1 1 d . . . . .
I7 I 0.18521(19) 0.7500 0.02583(6) 0.0980(6) Uani 1 2 d S T P . .
I9 I 0.63467(14) 1.2500 0.09647(6) 0.0785(5) Uani 1 2 d S T P . .
I10 I 0.73451(11) 0.98689(13) 0.22997(5) 0.0899(4) Uani 1 1 d . . . . .
I11 I 0.4877(2) 1.2500 0.30179(6) 0.1039(6) Uani 1 2 d S T P . .
N1 N 0.341(2) 0.2500 0.5199(3) 0.217(6) Uani 1 2 d DS TU P . .
H1A H 0.2796 0.2500 0.4940 0.325 Uiso 1 2 d R U P . .
H1B H 0.3872 0.3357 0.5188 0.325 Uiso 1 1 d R U . . .
N2 N 0.524(3) 0.311(4) 0.7277(6) 0.205(4) Uani 0.5 1 d D U P . .
H2A H 0.6034 0.3088 0.7414 0.307 Uiso 0.5 1 d R U P . .
H2B H 0.4977 0.4107 0.7261 0.307 Uiso 0.5 1 d R U P . .
H2C H 0.4813 0.2498 0.7463 0.307 Uiso 1 2 d R U P . .
N3 N 0.1538(18) 0.2500 0.2265(7) 0.251(6) Uani 1 2 d DS TU P . .
H3C H 0.1308 0.1877 0.2002 0.377 Uiso 0.5 1 d R U P . .
H3D H 0.1646 0.3477 0.2162 0.377 Uiso 0.5 1 d R U P . .
H3E H 0.2239 0.2145 0.2442 0.377 Uiso 0.5 1 d R U P . .
N4 N -0.1790(8) 0.3505(15) 0.3826(4) 0.252(4) Uani 0.5 1 d D U P . .
H4C H -0.1932 0.3728 0.4130 0.378 Uiso 0.5 1 d R U P . .
H4D H -0.1720 0.4397 0.3662 0.378 Uiso 0.5 1 d R U P . .
H4E H -0.2411 0.2940 0.3663 0.378 Uiso 0.5 1 d R U P . .
N5 N 0.8548(14) 0.7500 -0.0333(11) 0.263(11) Uani 1 2 d DS TU P . .
H5A H 0.8643 0.7500 -0.0650 0.395 Uiso 1 2 d R U P . .
H5B H 0.8900 0.8357 -0.0181 0.395 Uiso 1 1 d R U . . .
N6 N 0.641(2) 0.7500 0.1155(7) 0.241(12) Uani 1 2 d DS TU P . .
H6A H 0.5995 0.8036 0.1352 0.362 Uiso 0.5 1 d R U P . .
H6B H 0.6518 0.6512 0.1264 0.362 Uiso 0.5 1 d R U P . .
H6C H 0.7138 0.7952 0.1160 0.362 Uiso 0.5 1 d 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
I8' I8 0.549(4) . ?
I8' Bi2 3.216(3) . ?
I8' Bi3 3.295(3) . ?
I8 Bi3 3.206(3) . ?
I8 Bi2 3.282(3) . ?
Bi1 I4 2.9395(14) 4_565 ?
Bi1 I4 2.9395(14) . ?
Bi1 I3 3.0007(19) . ?
Bi1 I1 3.170(2) . ?
Bi1 I2 3.2710(11) . ?
Bi1 I2 3.2710(11) 2_746 ?
Bi2 I6 2.9337(15) . ?
Bi2 I6 2.9337(15) 4_575 ?
Bi2 I5 3.030(2) . ?
Bi2 I7 3.118(2) . ?
Bi2 I8' 3.216(3) 4_575 ?
Bi2 I8 3.282(3) 4_575 ?
Bi3 I10 2.9381(15) 4_585 ?
Bi3 I10 2.9381(15) . ?
Bi3 I9 3.010(2) . ?
Bi3 I11 3.155(2) . ?
Bi3 I8 3.206(3) 4_585 ?
Bi3 I8' 3.295(3) 4_585 ?
C1 N1 1.383(15) . ?
C1 C2 1.397(15) 4_565 ?
C1 C2 1.397(15) . ?
C1 H1D 0.9600 . ?
C2 C2 1.24(4) 4_565 ?
C2 C3 1.397(15) . ?
C2 H2D 0.9600 . ?
C2 H2E 0.9598 . ?
C3 C2 1.397(15) 4_565 ?
C3 C4 1.399(16) . ?
C3 H3A 0.9599 . ?
C4 N2 1.388(16) 4_565 ?
C4 N2 1.388(16) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C5 N3 1.381(16) . ?
C5 C6 1.393(16) . ?
C5 C6 1.393(16) 4_565 ?
C5 H5D 0.9600 . ?
C5 H5E 0.9600 . ?
C6 C7 1.382(15) . ?
C6 C6 1.47(4) 4_565 ?
C6 H6D 0.9601 . ?
C6 H6E 0.9600 . ?
C7 C6 1.382(15) 4_565 ?
C7 C8 1.398(11) . ?
C7 H7A 0.9601 . ?
C7 H7B 0.9600 . ?
C8 N4 1.404(8) . ?
C8 N4 1.404(8) 4_565 ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C9 C10 1.383(14) . ?
C9 N5 1.399(16) . ?
C9 H9A 0.9599 . ?
C10 C11 1.392(16) 4_575 ?
C10 C11 1.392(16) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C11 C11 1.28(4) 4_575 ?
C11 C12 1.411(16) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C12 N6 1.388(16) . ?
C12 C11 1.411(16) 4_575 ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
I2 Bi1 3.2711(11) 3_766 ?
N1 H1A 0.8998 . ?
N1 H1B 0.9000 . ?
N2 N2 1.05(7) 4_565 ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
N2 H2C 0.9248 . ?
N3 H3C 0.8999 . ?
N3 H3D 0.9000 . ?
N3 H3E 0.8999 . ?
N4 N4 1.72(3) 4_565 ?
N4 H4C 0.9001 . ?
N4 H4D 0.9000 . ?
N4 H4E 0.9000 . ?
N5 H5A 0.9002 . ?
N5 H5B 0.9000 . ?
N6 H6A 0.9001 . ?
N6 H6B 0.9000 . ?
N6 H6C 0.9000 . ?

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
I8 I8' Bi2 92.0(4) . . ?
I8 I8' Bi3 76.0(4) . . ?
Bi2 I8' Bi3 166.02(10) . . ?
I8' I8 Bi3 94.5(4) . . ?
I8' I8 Bi2 78.4(4) . . ?
Bi3 I8 Bi2 169.91(10) . . ?
I4 Bi1 I4 94.98(6) 4_565 . ?
I4 Bi1 I3 93.51(4) 4_565 . ?
I4 Bi1 I3 93.51(4) . . ?
I4 Bi1 I1 89.22(4) 4_565 . ?
I4 Bi1 I1 89.22(4) . . ?
I3 Bi1 I1 175.96(5) . . ?
I4 Bi1 I2 173.15(3) 4_565 . ?
I4 Bi1 I2 91.53(4) . . ?
I3 Bi1 I2 88.24(4) . . ?
I1 Bi1 I2 88.71(4) . . ?
I4 Bi1 I2 91.53(4) 4_565 2_746 ?
I4 Bi1 I2 173.15(3) . 2_746 ?
I3 Bi1 I2 88.24(4) . 2_746 ?
I1 Bi1 I2 88.71(4) . 2_746 ?
I2 Bi1 I2 81.90(4) . 2_746 ?
I6 Bi2 I6 95.87(6) . 4_575 ?
I6 Bi2 I5 92.36(4) . . ?
I6 Bi2 I5 92.36(4) 4_575 . ?
I6 Bi2 I7 91.68(4) . . ?
I6 Bi2 I7 91.69(4) 4_575 . ?
I5 Bi2 I7 173.96(6) . . ?
I6 Bi2 I8' 169.32(6) . 4_575 ?
I6 Bi2 I8' 94.43(6) 4_575 4_575 ?
I5 Bi2 I8' 90.02(6) . 4_575 ?
I7 Bi2 I8' 85.19(6) . 4_575 ?
I6 Bi2 I8' 94.43(6) . . ?
I6 Bi2 I8' 169.32(6) 4_575 . ?
I5 Bi2 I8' 90.02(6) . . ?
I7 Bi2 I8' 85.19(6) . . ?
I8' Bi2 I8' 75.15(10) 4_575 . ?
I6 Bi2 I8 177.92(6) . 4_575 ?
I6 Bi2 I8 85.75(6) 4_575 4_575 ?
I5 Bi2 I8 86.26(6) . 4_575 ?
I7 Bi2 I8 89.57(6) . 4_575 ?
I8' Bi2 I8 9.62(7) 4_575 4_575 ?
I8' Bi2 I8 84.02(7) . 4_575 ?
I6 Bi2 I8 85.75(6) . . ?
I6 Bi2 I8 177.92(6) 4_575 . ?
I5 Bi2 I8 86.26(6) . . ?
I7 Bi2 I8 89.57(6) . . ?
I8' Bi2 I8 84.02(7) 4_575 . ?
I8' Bi2 I8 9.62(7) . . ?
I8 Bi2 I8 92.61(10) 4_575 . ?
I10 Bi3 I10 100.33(6) 4_585 . ?
I10 Bi3 I9 92.32(4) 4_585 . ?
I10 Bi3 I9 92.32(4) . . ?
I10 Bi3 I11 89.88(4) 4_585 . ?
I10 Bi3 I11 89.87(4) . . ?
I9 Bi3 I11 176.57(5) . . ?
I10 Bi3 I8 166.14(6) 4_585 . ?
I10 Bi3 I8 93.08(6) . . ?
I9 Bi3 I8 90.59(6) . . ?
I11 Bi3 I8 86.66(7) . . ?
I10 Bi3 I8 93.08(6) 4_585 4_585 ?
I10 Bi3 I8 166.14(6) . 4_585 ?
I9 Bi3 I8 90.59(6) . 4_585 ?
I11 Bi3 I8 86.66(7) . 4_585 ?
I8 Bi3 I8 73.34(10) . 4_585 ?
I10 Bi3 I8' 84.90(6) 4_585 4_585 ?
I10 Bi3 I8' 174.57(6) . 4_585 ?
I9 Bi3 I8' 85.99(6) . 4_585 ?
I11 Bi3 I8' 91.58(6) . 4_585 ?
I8 Bi3 I8' 81.79(7) . 4_585 ?
I8 Bi3 I8' 9.56(7) 4_585 4_585 ?
I10 Bi3 I8' 174.57(6) 4_585 . ?
I10 Bi3 I8' 84.90(6) . . ?
I9 Bi3 I8' 85.99(6) . . ?
I11 Bi3 I8' 91.58(6) . . ?
I8 Bi3 I8' 9.56(7) . . ?
I8 Bi3 I8' 81.79(7) 4_585 . ?
I8' Bi3 I8' 89.83(10) 4_585 . ?
N1 C1 C2 115.5(14) . 4_565 ?
N1 C1 C2 115.5(14) . . ?
C2 C1 C2 52.8(18) 4_565 . ?
N1 C1 H1D 104.3 . . ?
C2 C1 H1D 132.1 4_565 . ?
C2 C1 H1D 87.1 . . ?
C2 C2 C3 63.6(8) 4_565 . ?
C2 C2 C1 63.6(9) 4_565 . ?
C3 C2 C1 110.2(15) . . ?
C2 C2 H2D 166.0 4_565 . ?
C3 C2 H2D 110.4 . . ?
C1 C2 H2D 109.9 . . ?
C2 C2 H2E 85.6 4_565 . ?
C3 C2 H2E 107.9 . . ?
C1 C2 H2E 110.0 . . ?
H2D C2 H2E 108.4 . . ?
C2 C3 C2 52.8(17) 4_565 . ?
C2 C3 C4 118.5(16) 4_565 . ?
C2 C3 C4 118.4(16) . . ?
C2 C3 H3A 84.9 4_565 . ?
C2 C3 H3A 129.4 . . ?
C4 C3 H3A 104.9 . . ?
N2 C4 N2 45(3) 4_565 . ?
N2 C4 C3 116.8(18) 4_565 . ?
N2 C4 C3 116.8(18) . . ?
N2 C4 H4A 143.4 4_565 . ?
N2 C4 H4A 113.7 . . ?
C3 C4 H4A 99.1 . . ?
N2 C4 H4B 69.5 4_565 . ?
N2 C4 H4B 111.1 . . ?
C3 C4 H4B 107.3 . . ?
H4A C4 H4B 107.8 . . ?
N3 C5 C6 148.1(8) . . ?
N3 C5 C6 148.1(8) . 4_565 ?
C6 C5 C6 63.6(15) . 4_565 ?
N3 C5 H5D 102.5 . . ?
C6 C5 H5D 108.8 . . ?
C6 C5 H5D 47.8 4_565 . ?
N3 C5 H5E 91.2 . . ?
C6 C5 H5E 87.0 . . ?
C6 C5 H5E 87.0 4_565 . ?
H5D C5 H5E 104.3 . . ?
C7 C6 C5 115.6(14) . . ?
C7 C6 C6 57.9(7) . 4_565 ?
C5 C6 C6 58.2(8) . 4_565 ?
C7 C6 H6D 94.1 . . ?
C5 C6 H6D 95.2 . . ?
C6 C6 H6D 92.1 4_565 . ?
C7 C6 H6E 118.7 . . ?
C5 C6 H6E 118.4 . . ?
C6 C6 H6E 160.5 4_565 . ?
H6D C6 H6E 107.5 . . ?
C6 C7 C6 64.2(15) 4_565 . ?
C6 C7 C8 143.7(9) 4_565 . ?
C6 C7 C8 143.7(9) . . ?
C6 C7 H7A 108.9 4_565 . ?
C6 C7 H7A 89.4 . . ?
C8 C7 H7A 96.4 . . ?
C6 C7 H7B 44.4 4_565 . ?
C6 C7 H7B 108.4 . . ?
C8 C7 H7B 104.5 . . ?
H7A C7 H7B 105.6 . . ?
C7 C8 N4 141.0(7) . . ?
C7 C8 N4 141.0(7) . 4_565 ?
N4 C8 N4 75.7(12) . 4_565 ?
C7 C8 H8A 108.8 . . ?
N4 C8 H8A 100.1 . . ?
N4 C8 H8A 62.6 4_565 . ?
C7 C8 H8B 95.2 . . ?
N4 C8 H8B 102.3 . . ?
N4 C8 H8B 55.7 4_565 . ?
H8A C8 H8B 104.7 . . ?
C10 C9 N5 131.6(18) . . ?
C10 C9 H9A 102.3 . . ?
N5 C9 H9A 105.5 . . ?
C9 C10 C11 131.9(10) . 4_575 ?
C9 C10 C11 131.9(10) . . ?
C11 C10 C11 54.6(18) 4_575 . ?
C9 C10 H10A 107.1 . . ?
C11 C10 H10A 53.4 4_575 . ?
C11 C10 H10A 106.1 . . ?
C9 C10 H10B 94.6 . . ?
C11 C10 H10B 131.6 4_575 . ?
C11 C10 H10B 107.8 . . ?
H10A C10 H10B 107.0 . . ?
C11 C11 C10 62.7(9) 4_575 . ?
C11 C11 C12 63.1(9) 4_575 . ?
C10 C11 C12 113.7(14) . . ?
C11 C11 H11A 157.3 4_575 . ?
C10 C11 H11A 108.2 . . ?
C12 C11 H11A 107.2 . . ?
C11 C11 H11B 94.9 4_575 . ?
C10 C11 H11B 108.4 . . ?
C12 C11 H11B 111.3 . . ?
H11A C11 H11B 107.8 . . ?
N6 C12 C11 109.7(13) . . ?
N6 C12 C11 109.7(13) . 4_575 ?
C11 C12 C11 53.8(18) . 4_575 ?
N6 C12 H12A 120.6 . . ?
C11 C12 H12A 106.3 . . ?
C11 C12 H12A 129.7 4_575 . ?
N6 C12 H12B 106.7 . . ?
C11 C12 H12B 105.7 . . ?
C11 C12 H12B 53.6 4_575 . ?
H12A C12 H12B 106.9 . . ?
Bi1 I2 Bi1 179.999(18) . 3_766 ?
C1 N1 H1A 120.3 . . ?
C1 N1 H1B 103.8 . . ?
H1A N1 H1B 109.5 . . ?
N2 N2 C4 67.7(15) 4_565 . ?
N2 N2 H2A 88.6 4_565 . ?
C4 N2 H2A 102.7 . . ?
N2 N2 H2B 161.2 4_565 . ?
C4 N2 H2B 111.4 . . ?
H2A N2 H2B 109.5 . . ?
N2 N2 H2C 55.2 4_565 . ?
C4 N2 H2C 112.2 . . ?
H2A N2 H2C 108.8 . . ?
H2B N2 H2C 111.7 . . ?
C5 N3 H3C 117.8 . . ?
C5 N3 H3D 110.8 . . ?
H3C N3 H3D 109.5 . . ?
C5 N3 H3E 99.3 . . ?
H3C N3 H3E 109.5 . . ?
H3D N3 H3E 109.5 . . ?
C8 N4 N4 52.1(6) . 4_565 ?
C8 N4 H4C 135.3 . . ?
N4 N4 H4C 102.3 4_565 . ?
C8 N4 H4D 102.3 . . ?
N4 N4 H4D 148.2 4_565 . ?
H4C N4 H4D 109.5 . . ?
C8 N4 H4E 87.7 . . ?
N4 N4 H4E 57.4 4_565 . ?
H4C N4 H4E 109.5 . . ?
H4D N4 H4E 109.5 . . ?
C9 N5 H5A 117.8 . . ?
C9 N5 H5B 105.2 . . ?
H5A N5 H5B 109.5 . . ?
C12 N6 H6A 96.9 . . ?
C12 N6 H6B 108.1 . . ?
H6A N6 H6B 109.5 . . ?
C12 N6 H6C 122.4 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 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
Bi2 I8' I8 Bi3 172.80(7) . . . . ?
Bi3 I8' I8 Bi2 -172.80(7) . . . . ?
N1 C1 C2 C2 -103.7(11) . . . 4_565 ?
N1 C1 C2 C3 -148.3(14) . . . . ?
C2 C1 C2 C3 -44.6(19) 4_565 . . . ?
C1 C2 C3 C2 45(2) . . . 4_565 ?
C2 C2 C3 C4 105.6(13) 4_565 . . . ?
C1 C2 C3 C4 150.2(13) . . . . ?
C2 C3 C4 N2 -124(2) 4_565 . . 4_565 ?
C2 C3 C4 N2 175(2) . . . 4_565 ?
C2 C3 C4 N2 -175(2) 4_565 . . . ?
C2 C3 C4 N2 124(2) . . . . ?
N3 C5 C6 C7 -168(2) . . . . ?
C6 C5 C6 C7 8(2) 4_565 . . . ?
N3 C5 C6 C6 -176(3) . . . 4_565 ?
C5 C6 C7 C6 -8(2) . . . 4_565 ?
C5 C6 C7 C8 -156.5(13) . . . . ?
C6 C6 C7 C8 -149(2) 4_565 . . . ?
C6 C7 C8 N4 -141.2(18) 4_565 . . . ?
C6 C7 C8 N4 -14(3) . . . . ?
C6 C7 C8 N4 14(3) 4_565 . . 4_565 ?
C6 C7 C8 N4 141.2(18) . . . 4_565 ?
N5 C9 C10 C11 142.0(14) . . . 4_575 ?
N5 C9 C10 C11 -142.0(14) . . . . ?
C9 C10 C11 C11 -117.6(14) . . . 4_575 ?
C9 C10 C11 C12 -156.0(10) . . . . ?
C11 C10 C11 C12 -38.5(17) 4_575 . . . ?
C11 C11 C12 N6 -100.4(8) 4_575 . . . ?
C10 C11 C12 N6 -62.1(18) . . . . ?
C10 C11 C12 C11 38.3(17) . . . 4_575 ?
C3 C4 N2 N2 101.9(13) . . . 4_565 ?
C7 C8 N4 N4 164(2) . . . 4_565 ?

_refine_diff_density_max         1.190
_refine_diff_density_min         -1.368
_refine_diff_density_rms         0.246



