#------------------------------------------------------------------------------
#$Date: 2022-08-24 01:33:25 +0300 (Wed, 24 Aug 2022) $
#$Revision: 277360 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/53/7245366.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245366
loop_
_publ_author_name
'Peloquin, Andrew J.'
'McMillen, Colin'
'Pennington, William'
_publ_section_title
;
 Isolation of unique heterocycles formed from pyridine-thiocarboxamides as
 diiodine, iodide, or polyiodide salts
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00904H
_journal_year                    2022
_chemical_formula_moiety         'Bi4 I16, 4(C H4 O), 4(C10 H9 N6)'
_chemical_formula_sum            'C44 H52 Bi4 I16 N24 O4'
_chemical_formula_weight         3847.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-03-14
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                108.4490(10)
_cell_angle_beta                 99.637(2)
_cell_angle_gamma                115.4060(10)
_cell_formula_units_Z            1
_cell_length_a                   13.1812(4)
_cell_length_b                   13.8011(4)
_cell_length_c                   14.1644(5)
_cell_measurement_reflns_used    9832
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.51
_cell_volume                     2065.08(12)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 2'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            59364
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.319
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    14.528
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2 (Bruker AXS Inc., 2017)'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.094
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.078
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         2.163
_refine_diff_density_min         -1.896
_refine_diff_density_rms         0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         9485
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.241
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0320
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+20.8472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8369
_reflns_number_total             9485
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00904h2.cif
_cod_data_source_block           mo_d8_5538_11oct21_ajp6_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7245366
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_max   0.397
_shelx_estimated_absorpt_t_min   0.150
_olex2_refinement_description
;
1. Restrained distances
 HN10-N10
 0.86 with sigma of 0.02
 HN4-N4
 0.86 with sigma of 0.02
 HN7A-N7
 0.86 with sigma of 0.02
 HN1A-N1
 0.86 with sigma of 0.02
 HN1B-N1
 0.86 with sigma of 0.02
 N7-HN7B
 0.86 with sigma of 0.02
 H1O1-O1
 0.85 with sigma of 0.02
 H1O2-O2
 0.85 with sigma of 0.02
 C1-HN10 \\sim C6-HN10
 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C3(H3), C4(H4A),
 C5(H5), C8(H8), C9(H9), C10(H10A)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.60352(2) 0.20056(2) 0.34097(2) 0.01849(6) Uani 1 1 d . . . . .
Bi2 Bi 0.36275(2) 0.06301(2) 0.53600(2) 0.01758(6) Uani 1 1 d . . . . .
I1 I 0.55396(5) 0.17512(4) 0.12321(4) 0.02472(10) Uani 1 1 d . . . . .
I2 I 0.86086(5) 0.33958(5) 0.39512(4) 0.03041(11) Uani 1 1 d . . . . .
I3 I 0.57961(5) 0.40857(4) 0.43531(4) 0.02457(10) Uani 1 1 d . . . . .
I4 I 0.65376(4) 0.18975(4) 0.57154(3) 0.01885(9) Uani 1 1 d . . . . .
I5 I 0.30949(4) 0.04746(4) 0.31021(3) 0.02116(9) Uani 1 1 d . . . . .
I6 I 0.11164(4) -0.05686(5) 0.50911(4) 0.02864(11) Uani 1 1 d . . . . .
I7 I 0.43288(4) 0.06828(4) 0.75721(3) 0.02001(9) Uani 1 1 d . . . . .
I8 I 0.41030(5) 0.30829(4) 0.63400(4) 0.02369(10) Uani 1 1 d . . . . .
O1 O 0.7564(5) 0.7124(5) 0.6528(4) 0.0280(11) Uani 1 1 d D . . . .
H1O1 H 0.691(8) 0.708(16) 0.627(13) 0.15(7) Uiso 1 1 d D . . . .
C21 C 0.8418(7) 0.7479(8) 0.6031(7) 0.0339(18) Uani 1 1 d . . . . .
H21A H 0.801760 0.703885 0.525642 0.051 Uiso 1 1 calc R U . . .
H21B H 0.904230 0.730718 0.625478 0.051 Uiso 1 1 calc R U . . .
H21C H 0.878543 0.833577 0.623832 0.051 Uiso 1 1 calc R U . . .
O2 O 0.7529(5) 0.4978(5) 0.7535(5) 0.0325(12) Uani 1 1 d D . . . .
H1O2 H 0.679(3) 0.448(6) 0.715(6) 0.039 Uiso 1 1 d D U . . .
C22 C 0.8430(8) 0.5244(8) 0.7039(6) 0.0329(18) Uani 1 1 d . . . . .
H22A H 0.806735 0.512841 0.632037 0.049 Uiso 1 1 calc R U . . .
H22B H 0.874344 0.470927 0.699929 0.049 Uiso 1 1 calc R U . . .
H22C H 0.908777 0.607217 0.746384 0.049 Uiso 1 1 calc R U . . .
N1 N 0.5826(6) 0.6301(6) 0.8234(6) 0.0278(14) Uani 1 1 d D . . . .
HN1A H 0.570(12) 0.638(12) 0.765(6) 0.09(5) Uiso 1 1 d D . . . .
HN1B H 0.528(9) 0.615(12) 0.852(10) 0.10(5) Uiso 1 1 d D . . . .
N2 N 0.8681(6) 0.8171(5) 1.0313(5) 0.0215(12) Uani 1 1 d . . . . .
N3 N 0.6851(6) 0.7308(6) 1.0691(5) 0.0268(14) Uani 1 1 d . . . . .
N4 N 0.7931(6) 0.7509(5) 0.8596(5) 0.0220(12) Uani 1 1 d D . . . .
HN4 H 0.794(9) 0.743(9) 0.797(4) 0.05(3) Uiso 1 1 d D . . . .
N5 N 1.0164(6) 0.8576(6) 0.8390(5) 0.0271(14) Uani 1 1 d . . . . .
N6 N 1.1092(6) 0.9399(6) 1.0288(5) 0.0284(14) Uani 1 1 d . . . . .
C11 C 0.6955(7) 0.7050(6) 0.8892(6) 0.0230(15) Uani 1 1 d . . . . .
C12 C 0.7434(7) 0.7483(6) 1.0011(6) 0.0221(14) Uani 1 1 d . . . . .
C13 C 0.7522(8) 0.7807(7) 1.1683(6) 0.0289(17) Uani 1 1 d . . . . .
H13 H 0.713996 0.770705 1.218550 0.035 Uiso 1 1 calc R U . . .
C14 C 0.8801(8) 0.8496(7) 1.2064(6) 0.0325(18) Uani 1 1 d . . . . .
H14 H 0.924386 0.883090 1.280025 0.039 Uiso 1 1 calc R U . . .
C15 C 0.9388(7) 0.8675(7) 1.1380(6) 0.0256(15) Uani 1 1 d . . . . .
H15 H 1.024032 0.912292 1.161648 0.031 Uiso 1 1 calc R U . . .
C16 C 0.8980(7) 0.8188(6) 0.9442(6) 0.0250(15) Uani 1 1 d . . . . .
C17 C 1.0153(7) 0.8751(6) 0.9376(6) 0.0249(15) Uani 1 1 d . . . . .
C18 C 1.1257(7) 0.9085(7) 0.8327(6) 0.0265(16) Uani 1 1 d . . . . .
H18 H 1.131629 0.898130 0.764629 0.032 Uiso 1 1 calc R U . . .
C19 C 1.2300(7) 0.9753(7) 0.9204(6) 0.0266(16) Uani 1 1 d . . . . .
H19 H 1.306728 1.010597 0.914031 0.032 Uiso 1 1 calc R U . . .
C20 C 1.2178(7) 0.9886(7) 1.0186(6) 0.0296(17) Uani 1 1 d . . . . .
H20 H 1.287987 1.033402 1.080560 0.036 Uiso 1 1 calc R U . . .
N7 N 0.5733(7) 0.4218(7) 0.9206(6) 0.0354(16) Uani 1 1 d D . . . .
HN7A H 0.564(10) 0.394(9) 0.854(3) 0.05(3) Uiso 1 1 d D . . . .
HN7B H 0.526(8) 0.390(9) 0.952(8) 0.064 Uiso 1 1 d D U . . .
N8 N 0.8621(6) 0.5724(5) 1.1258(5) 0.0250(13) Uani 1 1 d . . . . .
N9 N 0.6748(6) 0.4875(6) 1.1588(6) 0.0307(15) Uani 1 1 d . . . . .
N10 N 0.7880(6) 0.5232(5) 0.9558(5) 0.0236(13) Uani 1 1 d D . . . .
HN10 H 0.7848(18) 0.514(7) 0.891(2) 0.05(3) Uiso 1 1 d D . . . .
N11 N 1.0128(6) 0.6309(6) 0.9402(5) 0.0309(15) Uani 1 1 d . . . . .
N12 N 1.1029(6) 0.6841(6) 1.1261(6) 0.0313(15) Uani 1 1 d . . . . .
C1 C 0.6899(7) 0.4787(7) 0.9852(6) 0.0286(16) Uani 1 1 d D . . . .
C2 C 0.7345(7) 0.5098(6) 1.0938(6) 0.0267(16) Uani 1 1 d . . . . .
C3 C 0.7428(8) 0.5273(7) 1.2576(7) 0.0308(17) Uani 1 1 d . . . . .
H3 H 0.703022 0.511521 1.305713 0.037 Uiso 1 1 calc R U . . .
C4 C 0.8691(9) 0.5911(8) 1.2982(7) 0.036(2) Uani 1 1 d . . . . .
H4A H 0.911738 0.617994 1.371028 0.044 Uiso 1 1 calc R U . . .
C5 C 0.9303(8) 0.6142(7) 1.2295(7) 0.0331(18) Uani 1 1 d . . . . .
H5 H 1.015554 0.656878 1.253401 0.040 Uiso 1 1 calc R U . . .
C6 C 0.8922(7) 0.5794(6) 1.0405(6) 0.0221(14) Uani 1 1 d D . . . .
C7 C 1.0110(7) 0.6354(6) 1.0350(6) 0.0224(14) Uani 1 1 d . . . . .
C8 C 1.1270(7) 0.6831(7) 0.9373(7) 0.0307(17) Uani 1 1 d . . . . .
H8 H 1.136988 0.681195 0.871938 0.037 Uiso 1 1 calc R U . . .
C9 C 1.2260(8) 0.7374(7) 1.0258(7) 0.0299(17) Uani 1 1 d . . . . .
H9 H 1.303768 0.775530 1.022254 0.036 Uiso 1 1 calc R U . . .
C10 C 1.2139(8) 0.7373(7) 1.1213(7) 0.0328(18) Uani 1 1 d . . . . .
H10A H 1.283012 0.774298 1.182775 0.039 Uiso 1 1 calc R U . . .
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'
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 I3 98.278(15) . . ?
I1 Bi1 I4 171.554(15) . . ?
I1 Bi1 I5 94.161(14) . . ?
I1 Bi1 I7 86.327(13) . 2_656 ?
I2 Bi1 I1 92.804(16) . . ?
I2 Bi1 I3 94.595(16) . . ?
I2 Bi1 I4 88.493(15) . . ?
I2 Bi1 I5 172.912(16) . . ?
I2 Bi1 I7 98.546(15) . 2_656 ?
I3 Bi1 I4 89.930(13) . . ?
I3 Bi1 I5 83.108(14) . . ?
I3 Bi1 I7 165.855(15) . 2_656 ?
I4 Bi1 I5 84.808(12) . . ?
I4 Bi1 I7 85.227(12) . 2_656 ?
I7 Bi1 I5 83.224(12) 2_656 . ?
I4 Bi2 I4 86.815(13) 2_656 . ?
I5 Bi2 I4 85.531(13) . 2_656 ?
I5 Bi2 I4 89.332(13) . . ?
I5 Bi2 I7 174.118(15) . . ?
I6 Bi2 I4 176.629(15) . . ?
I6 Bi2 I4 90.692(15) . 2_656 ?
I6 Bi2 I5 92.738(16) . . ?
I6 Bi2 I7 91.092(15) . . ?
I6 Bi2 I8 96.805(16) . . ?
I7 Bi2 I4 89.963(13) . 2_656 ?
I7 Bi2 I4 86.641(13) . . ?
I8 Bi2 I4 172.454(15) . 2_656 ?
I8 Bi2 I4 85.728(14) . . ?
I8 Bi2 I5 93.224(14) . . ?
I8 Bi2 I7 90.752(14) . . ?
Bi1 I4 Bi2 91.391(13) . . ?
Bi2 I4 Bi1 91.080(12) 2_656 . ?
Bi2 I4 Bi2 93.186(13) 2_656 . ?
Bi2 I5 Bi1 93.959(14) . . ?
Bi2 I7 Bi1 93.341(13) . 2_656 ?
C21 O1 H1O1 116(10) . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 O2 H1O2 120(6) . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
HN1A N1 HN1B 120(10) . . ?
C11 N1 HN1A 112(10) . . ?
C11 N1 HN1B 117(10) . . ?
C15 N2 C12 118.8(6) . . ?
C16 N2 C12 109.7(6) . . ?
C16 N2 C15 131.4(7) . . ?
C13 N3 C12 115.8(7) . . ?
C11 N4 HN4 128(7) . . ?
C16 N4 HN4 120(7) . . ?
C16 N4 C11 112.0(6) . . ?
C18 N5 C17 115.0(7) . . ?
C17 N6 C20 115.1(6) . . ?
N1 C11 N4 125.6(7) . . ?
N1 C11 C12 129.1(7) . . ?
N4 C11 C12 105.2(6) . . ?
N2 C12 C11 106.6(6) . . ?
N3 C12 N2 124.4(7) . . ?
N3 C12 C11 128.9(7) . . ?
N3 C13 H13 118.1 . . ?
N3 C13 C14 123.8(7) . . ?
C14 C13 H13 118.1 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(8) . . ?
C15 C14 H14 119.8 . . ?
N2 C15 H15 121.6 . . ?
C14 C15 N2 116.7(8) . . ?
C14 C15 H15 121.6 . . ?
N2 C16 C17 128.8(7) . . ?
N4 C16 N2 106.4(7) . . ?
N4 C16 C17 124.8(7) . . ?
N5 C17 C16 115.1(7) . . ?
N6 C17 N5 127.8(7) . . ?
N6 C17 C16 117.1(7) . . ?
N5 C18 H18 118.5 . . ?
N5 C18 C19 123.0(7) . . ?
C19 C18 H18 118.5 . . ?
C18 C19 H19 121.6 . . ?
C18 C19 C20 116.9(7) . . ?
C20 C19 H19 121.6 . . ?
N6 C20 C19 122.1(8) . . ?
N6 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
HN7A N7 HN7B 128(10) . . ?
C1 N7 HN7A 113(7) . . ?
C1 N7 HN7B 110(8) . . ?
C5 N8 C2 119.5(7) . . ?
C6 N8 C2 108.6(6) . . ?
C6 N8 C5 131.9(7) . . ?
C3 N9 C2 114.9(7) . . ?
C1 N10 HN10 124.9(15) . . ?
C6 N10 HN10 124.3(15) . . ?
C6 N10 C1 110.7(6) . . ?
C7 N11 C8 113.3(7) . . ?
C7 N12 C10 115.6(7) . . ?
N7 C1 N10 125.4(7) . . ?
N7 C1 C2 128.1(7) . . ?
N10 C1 C2 106.5(7) . . ?
N9 C2 N8 124.2(7) . . ?
N9 C2 C1 129.3(8) . . ?
C1 C2 N8 106.6(6) . . ?
N9 C3 H3 117.1 . . ?
N9 C3 C4 125.8(8) . . ?
C4 C3 H3 117.1 . . ?
C3 C4 H4A 120.7 . . ?
C5 C4 C3 118.6(8) . . ?
C5 C4 H4A 120.7 . . ?
N8 C5 C4 117.0(8) . . ?
N8 C5 H5 121.5 . . ?
C4 C5 H5 121.5 . . ?
N8 C6 N10 107.6(6) . . ?
N8 C6 C7 128.4(7) . . ?
N10 C6 C7 124.0(6) . . ?
N11 C7 N12 129.7(7) . . ?
N11 C7 C6 114.8(7) . . ?
N12 C7 C6 115.5(6) . . ?
N11 C8 H8 119.2 . . ?
C9 C8 N11 121.6(7) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.4(8) . . ?
C10 C9 H9 119.8 . . ?
N12 C10 C9 119.4(8) . . ?
N12 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
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 2.9166(5) . ?
Bi1 I2 2.8963(6) . ?
Bi1 I3 2.9353(5) . ?
Bi1 I4 3.2857(5) . ?
Bi1 I5 3.3912(5) . ?
Bi1 I7 3.3037(5) 2_656 ?
Bi2 I4 3.3265(5) . ?
Bi2 I4 3.2266(5) 2_656 ?
Bi2 I5 3.0744(5) . ?
Bi2 I6 2.8842(6) . ?
Bi2 I7 3.0831(5) . ?
Bi2 I8 2.9483(5) . ?
O1 H1O1 0.85(2) . ?
O1 C21 1.419(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O2 H1O2 0.85(2) . ?
O2 C22 1.451(9) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N1 HN1A 0.86(2) . ?
N1 HN1B 0.86(2) . ?
N1 C11 1.326(10) . ?
N2 C12 1.398(10) . ?
N2 C15 1.394(9) . ?
N2 C16 1.361(9) . ?
N3 C12 1.347(9) . ?
N3 C13 1.297(10) . ?
N4 HN4 0.86(2) . ?
N4 C11 1.372(9) . ?
N4 C16 1.360(10) . ?
N5 C17 1.343(9) . ?
N5 C18 1.338(10) . ?
N6 C17 1.335(10) . ?
N6 C20 1.351(10) . ?
C11 C12 1.417(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.426(12) . ?
C14 H14 0.9500 . ?
C14 C15 1.355(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.438(11) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(10) . ?
C20 H20 0.9500 . ?
N7 HN7A 0.87(2) . ?
N7 HN7B 0.87(2) . ?
N7 C1 1.361(11) . ?
N8 C2 1.425(10) . ?
N8 C5 1.369(11) . ?
N8 C6 1.352(9) . ?
N9 C2 1.332(10) . ?
N9 C3 1.317(11) . ?
N10 HN10 0.87(2) . ?
N10 C1 1.373(9) . ?
N10 C6 1.369(10) . ?
N11 C7 1.330(9) . ?
N11 C8 1.376(10) . ?
N12 C7 1.346(10) . ?
N12 C10 1.352(11) . ?
C1 C2 1.400(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.407(13) . ?
C4 H4A 0.9500 . ?
C4 C5 1.393(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.448(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.363(12) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(11) . ?
C10 H10A 0.9500 . ?
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 C11 C12 N2 175.3(7) . . . . ?
N1 C11 C12 N3 -5.2(13) . . . . ?
N2 C16 C17 N5 177.8(7) . . . . ?
N2 C16 C17 N6 -3.6(11) . . . . ?
N3 C13 C14 C15 0.7(12) . . . . ?
N4 C11 C12 N2 -0.7(7) . . . . ?
N4 C11 C12 N3 178.8(7) . . . . ?
N4 C16 C17 N5 0.7(10) . . . . ?
N4 C16 C17 N6 179.3(7) . . . . ?
N5 C18 C19 C20 -0.1(11) . . . . ?
C11 N4 C16 N2 0.0(8) . . . . ?
C11 N4 C16 C17 177.7(6) . . . . ?
C12 N2 C15 C14 -2.5(10) . . . . ?
C12 N2 C16 N4 -0.4(7) . . . . ?
C12 N2 C16 C17 -178.0(7) . . . . ?
C12 N3 C13 C14 -0.5(11) . . . . ?
C13 N3 C12 N2 -1.3(10) . . . . ?
C13 N3 C12 C11 179.4(7) . . . . ?
C13 C14 C15 N2 0.8(11) . . . . ?
C15 N2 C12 N3 2.9(10) . . . . ?
C15 N2 C12 C11 -177.7(6) . . . . ?
C15 N2 C16 N4 177.7(7) . . . . ?
C15 N2 C16 C17 0.1(12) . . . . ?
C16 N2 C12 N3 -178.8(6) . . . . ?
C16 N2 C12 C11 0.7(7) . . . . ?
C16 N2 C15 C14 179.6(7) . . . . ?
C16 N4 C11 N1 -175.8(7) . . . . ?
C16 N4 C11 C12 0.4(8) . . . . ?
C17 N5 C18 C19 -0.7(11) . . . . ?
C17 N6 C20 C19 2.1(11) . . . . ?
C18 N5 C17 N6 2.5(11) . . . . ?
C18 N5 C17 C16 -179.0(6) . . . . ?
C18 C19 C20 N6 -0.7(12) . . . . ?
C20 N6 C17 N5 -3.2(11) . . . . ?
C20 N6 C17 C16 178.4(7) . . . . ?
N7 C1 C2 N8 -177.4(8) . . . . ?
N7 C1 C2 N9 3.1(14) . . . . ?
N8 C6 C7 N11 -178.1(7) . . . . ?
N8 C6 C7 N12 1.9(11) . . . . ?
N9 C3 C4 C5 -1.0(13) . . . . ?
N10 C1 C2 N8 -0.9(8) . . . . ?
N10 C1 C2 N9 179.6(7) . . . . ?
N10 C6 C7 N11 1.2(10) . . . . ?
N10 C6 C7 N12 -178.7(6) . . . . ?
N11 C8 C9 C10 2.6(12) . . . . ?
C1 N10 C6 N8 -0.6(8) . . . . ?
C1 N10 C6 C7 179.9(7) . . . . ?
C2 N8 C5 C4 0.6(10) . . . . ?
C2 N8 C6 N10 0.0(8) . . . . ?
C2 N8 C6 C7 179.5(7) . . . . ?
C2 N9 C3 C4 1.2(12) . . . . ?
C3 N9 C2 N8 -0.4(11) . . . . ?
C3 N9 C2 C1 179.1(8) . . . . ?
C3 C4 C5 N8 0.0(11) . . . . ?
C5 N8 C2 N9 -0.5(11) . . . . ?
C5 N8 C2 C1 180.0(6) . . . . ?
C5 N8 C6 N10 -179.3(7) . . . . ?
C5 N8 C6 C7 0.2(13) . . . . ?
C6 N8 C2 N9 -179.9(7) . . . . ?
C6 N8 C2 C1 0.5(8) . . . . ?
C6 N8 C5 C4 179.9(7) . . . . ?
C6 N10 C1 N7 177.5(7) . . . . ?
C6 N10 C1 C2 0.9(8) . . . . ?
C7 N11 C8 C9 -2.6(11) . . . . ?
C7 N12 C10 C9 -0.7(11) . . . . ?
C8 N11 C7 N12 1.1(11) . . . . ?
C8 N11 C7 C6 -178.9(6) . . . . ?
C8 C9 C10 N12 -0.8(12) . . . . ?
C10 N12 C7 N11 0.5(12) . . . . ?
C10 N12 C7 C6 -179.5(7) . . . . ?
