#------------------------------------------------------------------------------
#$Date: 2022-08-24 01:33:25 +0300 (Wed, 24 Aug 2022) $
#$Revision: 277360 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/53/7245368.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_7245368
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, 2(I2), 2(C28 H28 N8), 4(C2 H3 N)'
_chemical_formula_sum            'C64 H68 Bi4 I20 N20'
_chemical_formula_weight         4491.30
_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                109.244(2)
_cell_angle_beta                 91.431(2)
_cell_angle_gamma                97.814(2)
_cell_formula_units_Z            1
_cell_length_a                   11.1882(5)
_cell_length_b                   14.4203(6)
_cell_length_c                   17.1240(8)
_cell_measurement_reflns_used    9595
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      2.34
_cell_volume                     2576.9(2)
_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      100.01
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0500
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            127858
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.645
_diffrn_reflns_theta_min         2.155
_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    12.844
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4212
_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    2.894
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.157
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.086
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         2.745
_refine_diff_density_min         -3.268
_refine_diff_density_rms         0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         14514
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0096P)²+22.2653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12797
_reflns_number_total             14514
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00904h2.cif
_cod_data_source_block           mo_d8_5481_26sep21_ajp3_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               7245368
_shelx_shelxl_version_number     2018/3
_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   0.405
_shelx_estimated_absorpt_t_min   0.238
_olex2_refinement_description
;
1. Restrained distances
 N5-HN5
 0.86 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 N6(HN6), C3(H3), C4(H4A), C5(H5), C10(H10), C11(H11), C12(H12), C17(H17),
 C18(H18), C19(H19), C24(H24), C25(H25), C26(H26)
2.b X=CH2 refined with riding coordinates:
 N7(HN7A,HN7B)
2.c Idealised Me refined as rotating group:
 C7(H7C,H7D,H7E), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C28(H28A,H28B,
 H28C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C)
;
_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 0.58758(2) 0.44685(2) 0.86655(2) 0.01602(4) Uani 1 1 d . . . . .
Bi2 Bi 0.32433(2) 0.68981(2) 0.92618(2) 0.01970(4) Uani 1 1 d . . . . .
I1 I 0.58716(3) 0.25704(3) 0.73993(2) 0.02701(8) Uani 1 1 d . . . . .
I2 I 0.81239(3) 0.42905(3) 0.96246(2) 0.02266(7) Uani 1 1 d . . . . .
I3 I 0.73236(3) 0.55220(3) 0.77446(2) 0.02623(8) Uani 1 1 d . . . . .
I4 I 0.57499(3) 0.66235(2) 1.01702(2) 0.01739(6) Uani 1 1 d . . . . .
I5 I 0.34092(3) 0.47268(2) 0.79682(2) 0.02257(7) Uani 1 1 d . . . . .
I6 I 0.33167(6) 0.89683(3) 1.03293(3) 0.05460(15) Uani 1 1 d . . . . .
I7 I 0.08356(4) 0.67343(4) 0.85003(3) 0.04166(11) Uani 1 1 d . . . . .
I8 I 0.46777(4) 0.76593(3) 0.81059(3) 0.02948(8) Uani 1 1 d . . . . .
I9 I 0.37382(4) 0.65714(3) 0.61412(3) 0.03986(11) Uani 1 1 d . . . . .
I10 I 0.32083(4) 0.58592(4) 0.44457(4) 0.04637(12) Uani 1 1 d . . . . .
N1 N 0.7701(4) 0.0136(3) 0.4598(3) 0.0188(8) Uani 1 1 d . . . . .
N2 N 0.7504(4) 0.0492(3) 0.6741(3) 0.0158(8) Uani 1 1 d . . . . .
N3 N 0.8771(4) 0.1054(3) 0.5957(3) 0.0180(8) Uani 1 1 d . . . . .
N4 N 0.9629(4) 0.1284(4) 0.8018(3) 0.0254(10) Uani 1 1 d . . . . .
N5 N 0.9541(4) 0.1114(3) 0.4481(3) 0.0195(8) Uani 1 1 d D . . . .
HN5 H 0.962(6) 0.142(4) 0.5006(14) 0.022(16) Uiso 1 1 d D . . . .
N6 N 0.8167(4) 0.1026(4) 0.3001(3) 0.0231(9) Uani 1 1 d . . . . .
HN6 H 0.852633 0.160863 0.333408 0.028 Uiso 1 1 calc R U . . .
N7 N 1.0557(3) 0.0734(3) 0.3312(2) 0.0116(7) Uani 1 1 d . . . . .
HN7A H 0.994552 0.027009 0.305795 0.014 Uiso 1 1 calc R U . . .
HN7B H 1.119596 0.083328 0.304372 0.014 Uiso 1 1 calc R U . . .
N8 N 1.1413(4) 0.2320(3) 0.5342(3) 0.0227(9) Uani 1 1 d . . . . .
C1 C 0.7857(4) 0.0384(4) 0.5448(3) 0.0178(9) Uani 1 1 d . . . . .
C2 C 0.7032(4) 0.0018(3) 0.5925(3) 0.0158(9) Uani 1 1 d . . . . .
C3 C 0.6898(5) 0.0385(4) 0.7407(3) 0.0208(10) Uani 1 1 d . . . . .
H3 H 0.723374 0.072574 0.795957 0.025 Uiso 1 1 calc R U . . .
C4 C 0.5820(5) -0.0214(4) 0.7259(3) 0.0229(10) Uani 1 1 d . . . . .
H4A H 0.538573 -0.028962 0.770891 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5330(5) -0.0733(4) 0.6426(4) 0.0227(10) Uani 1 1 d . . . . .
H5 H 0.457420 -0.115754 0.633316 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5908(5) -0.0640(4) 0.5763(3) 0.0201(10) Uani 1 1 d . . . . .
C7 C 0.5415(5) -0.1204(4) 0.4885(3) 0.0239(11) Uani 1 1 d . . . . .
H7C H 0.545338 -0.074964 0.456567 0.036 Uiso 1 1 calc R U . . .
H7D H 0.457166 -0.150036 0.488191 0.036 Uiso 1 1 calc R U . . .
H7E H 0.589681 -0.173113 0.463442 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8560(4) 0.1109(4) 0.6725(3) 0.0178(9) Uani 1 1 d . . . . .
C9 C 0.9324(4) 0.1725(4) 0.7462(3) 0.0192(10) Uani 1 1 d . . . . .
C10 C 1.0295(6) 0.1783(5) 0.8733(4) 0.0332(13) Uani 1 1 d . . . . .
H10 H 1.047244 0.144646 0.910473 0.040 Uiso 1 1 calc R U . . .
C11 C 1.0719(5) 0.2775(5) 0.8929(4) 0.0352(14) Uani 1 1 d . . . . .
H11 H 1.118663 0.313452 0.943638 0.042 Uiso 1 1 calc R U . . .
C12 C 1.0455(5) 0.3242(4) 0.8376(4) 0.0304(13) Uani 1 1 d . . . . .
H12 H 1.075694 0.392772 0.850487 0.036 Uiso 1 1 calc R U . . .
C13 C 0.9755(5) 0.2738(4) 0.7630(3) 0.0224(10) Uani 1 1 d . . . . .
C14 C 0.9441(6) 0.3268(4) 0.7056(4) 0.0294(12) Uani 1 1 d . . . . .
H14A H 0.985843 0.303517 0.654657 0.044 Uiso 1 1 calc R U . . .
H14B H 0.969412 0.398446 0.732457 0.044 Uiso 1 1 calc R U . . .
H14C H 0.856502 0.313200 0.691828 0.044 Uiso 1 1 calc R U . . .
C15 C 0.8464(4) 0.0472(4) 0.4169(3) 0.0178(9) Uani 1 1 d . . . . .
C16 C 0.8072(5) 0.0244(4) 0.3288(3) 0.0188(9) Uani 1 1 d . . . . .
C17 C 0.7748(6) 0.0959(5) 0.2247(4) 0.0295(12) Uani 1 1 d . . . . .
H17 H 0.785416 0.152766 0.207737 0.035 Uiso 1 1 calc R U . . .
C18 C 0.7166(5) 0.0070(5) 0.1719(4) 0.0303(12) Uani 1 1 d . . . . .
H18 H 0.683534 0.001935 0.118763 0.036 Uiso 1 1 calc R U . . .
C19 C 0.7064(5) -0.0757(4) 0.1969(4) 0.0279(12) Uani 1 1 d . . . . .
H19 H 0.667131 -0.137961 0.159996 0.033 Uiso 1 1 calc R U . . .
C20 C 0.7530(5) -0.0694(4) 0.2761(3) 0.0224(10) Uani 1 1 d . . . . .
C21 C 0.7505(5) -0.1588(4) 0.3014(4) 0.0254(11) Uani 1 1 d . . . . .
H21A H 0.825855 -0.153484 0.334098 0.038 Uiso 1 1 calc R U . . .
H21B H 0.742243 -0.218392 0.251874 0.038 Uiso 1 1 calc R U . . .
H21C H 0.681714 -0.163517 0.334968 0.038 Uiso 1 1 calc R U . . .
C22 C 1.0520(4) 0.1236(4) 0.4029(3) 0.0183(9) Uani 1 1 d . . . . .
C23 C 1.1487(5) 0.2060(4) 0.4525(3) 0.0202(10) Uani 1 1 d . . . . .
C24 C 1.2233(5) 0.3062(4) 0.5844(4) 0.0262(11) Uani 1 1 d . . . . .
H24 H 1.220147 0.323711 0.642810 0.031 Uiso 1 1 calc R U . . .
C25 C 1.3127(5) 0.3577(4) 0.5526(4) 0.0311(13) Uani 1 1 d . . . . .
H25 H 1.370368 0.409616 0.588755 0.037 Uiso 1 1 calc R U . . .
C26 C 1.3158(5) 0.3324(4) 0.4689(4) 0.0302(13) Uani 1 1 d . . . . .
H26 H 1.374966 0.368700 0.446921 0.036 Uiso 1 1 calc R U . . .
C27 C 1.2344(5) 0.2546(4) 0.4145(4) 0.0221(10) Uani 1 1 d . . . . .
C28 C 1.2372(6) 0.2302(4) 0.3222(4) 0.0297(12) Uani 1 1 d . . . . .
H28A H 1.295417 0.280276 0.310455 0.045 Uiso 1 1 calc R U . . .
H28B H 1.156539 0.230035 0.298396 0.045 Uiso 1 1 calc R U . . .
H28C H 1.261328 0.164536 0.297689 0.045 Uiso 1 1 calc R U . . .
N9 N 0.9471(5) 0.3004(4) 0.3771(4) 0.0346(12) Uani 1 1 d . . . . .
C29 C 0.9506(6) 0.3822(5) 0.3836(4) 0.0345(14) Uani 1 1 d . . . . .
C30 C 0.9505(7) 0.4852(5) 0.3898(6) 0.0490(19) Uani 1 1 d . . . . .
H30A H 0.910605 0.487626 0.339068 0.074 Uiso 1 1 calc R U . . .
H30B H 1.034043 0.519358 0.396992 0.074 Uiso 1 1 calc R U . . .
H30C H 0.906798 0.518118 0.437589 0.074 Uiso 1 1 calc R U . . .
N10 N 1.0556(7) 0.0394(5) 0.1395(4) 0.0532(17) Uani 1 1 d . . . . .
C31 C 1.1119(7) 0.0900(5) 0.1117(4) 0.0388(15) Uani 1 1 d . . . . .
C32 C 1.1866(7) 0.1551(6) 0.0766(5) 0.0473(18) Uani 1 1 d . . . . .
H32A H 1.203163 0.117132 0.020028 0.071 Uiso 1 1 calc R U . . .
H32B H 1.263044 0.182290 0.110780 0.071 Uiso 1 1 calc R U . . .
H32C H 1.143765 0.209641 0.075515 0.071 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
I1 Bi1 I2 93.259(12) . . ?
I1 Bi1 I3 92.688(13) . . ?
I1 Bi1 I4 90.637(11) . 2_667 ?
I1 Bi1 I4 177.019(11) . . ?
I1 Bi1 I5 92.606(12) . . ?
I2 Bi1 I4 86.925(10) . 2_667 ?
I2 Bi1 I4 87.801(10) . . ?
I2 Bi1 I5 170.648(11) . . ?
I3 Bi1 I2 91.883(12) . . ?
I3 Bi1 I4 176.527(12) . 2_667 ?
I3 Bi1 I4 90.061(11) . . ?
I3 Bi1 I5 95.113(12) . . ?
I4 Bi1 I4 86.635(9) . 2_667 ?
I5 Bi1 I4 85.732(10) . 2_667 ?
I5 Bi1 I4 85.995(10) . . ?
I2 Bi2 I4 84.753(10) 2_667 . ?
I5 Bi2 I2 85.192(11) . 2_667 ?
I5 Bi2 I4 84.699(10) . . ?
I6 Bi2 I2 101.504(14) . 2_667 ?
I6 Bi2 I4 93.938(15) . . ?
I6 Bi2 I5 173.036(15) . . ?
I6 Bi2 I8 87.737(15) . . ?
I7 Bi2 I2 84.813(12) . 2_667 ?
I7 Bi2 I4 167.726(13) . . ?
I7 Bi2 I5 88.001(14) . . ?
I7 Bi2 I6 94.462(18) . . ?
I7 Bi2 I8 98.733(13) . . ?
I8 Bi2 I2 169.868(12) . 2_667 ?
I8 Bi2 I4 90.524(11) . . ?
I8 Bi2 I5 85.449(12) . . ?
Bi1 I2 Bi2 97.482(11) . 2_667 ?
Bi1 I4 Bi1 93.365(10) . 2_667 ?
Bi2 I4 Bi1 90.648(9) . 2_667 ?
Bi2 I4 Bi1 91.254(9) . . ?
Bi1 I5 Bi2 97.644(11) . . ?
C15 N1 C1 123.2(5) . . ?
C3 N2 C2 122.3(4) . . ?
C3 N2 C8 130.1(4) . . ?
C8 N2 C2 107.4(4) . . ?
C8 N3 C1 107.1(4) . . ?
C10 N4 C9 123.0(5) . . ?
C15 N5 HN5 116(4) . . ?
C22 N5 HN5 118(4) . . ?
C22 N5 C15 125.5(4) . . ?
C16 N6 HN6 118.0 . . ?
C17 N6 HN6 118.0 . . ?
C17 N6 C16 123.9(5) . . ?
HN7A N7 HN7B 120.0 . . ?
C22 N7 HN7A 120.0 . . ?
C22 N7 HN7B 120.0 . . ?
C23 N8 C24 118.8(5) . . ?
N1 C1 C2 123.9(4) . . ?
N3 C1 N1 126.1(4) . . ?
N3 C1 C2 109.9(4) . . ?
N2 C2 C1 104.7(4) . . ?
N2 C2 C6 119.1(4) . . ?
C1 C2 C6 136.1(5) . . ?
N2 C3 H3 120.6 . . ?
C4 C3 N2 118.7(5) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4A 119.9 . . ?
C3 C4 C5 120.2(5) . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.1(5) . . ?
C6 C5 H5 119.0 . . ?
C2 C6 C7 120.1(5) . . ?
C5 C6 C2 117.5(5) . . ?
C5 C6 C7 122.4(5) . . ?
C6 C7 H7C 109.5 . . ?
C6 C7 H7D 109.5 . . ?
C6 C7 H7E 109.5 . . ?
H7C C7 H7D 109.5 . . ?
H7C C7 H7E 109.5 . . ?
H7D C7 H7E 109.5 . . ?
N2 C8 C9 123.8(4) . . ?
N3 C8 N2 110.9(4) . . ?
N3 C8 C9 125.3(4) . . ?
N4 C9 C8 117.5(5) . . ?
N4 C9 C13 118.9(5) . . ?
C13 C9 C8 123.6(5) . . ?
N4 C10 H10 119.9 . . ?
N4 C10 C11 120.2(6) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.6(6) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.0 . . ?
C11 C12 C13 122.1(6) . . ?
C13 C12 H12 119.0 . . ?
C9 C13 C14 121.6(5) . . ?
C12 C13 C9 117.2(5) . . ?
C12 C13 C14 121.1(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 N5 125.8(5) . . ?
N1 C15 C16 115.7(5) . . ?
N5 C15 C16 118.0(4) . . ?
N6 C16 C15 116.7(4) . . ?
N6 C16 C20 118.9(5) . . ?
C20 C16 C15 124.3(5) . . ?
N6 C17 H17 120.2 . . ?
N6 C17 C18 119.6(5) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.1(5) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.3(5) . . ?
C20 C19 H19 119.4 . . ?
C16 C20 C19 117.1(5) . . ?
C16 C20 C21 121.1(5) . . ?
C19 C20 C21 121.8(5) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 C23 112.3(4) . . ?
N7 C22 N5 122.5(5) . . ?
N7 C22 C23 125.1(5) . . ?
N8 C23 C22 114.1(4) . . ?
N8 C23 C27 123.8(5) . . ?
C27 C23 C22 122.0(5) . . ?
N8 C24 H24 119.3 . . ?
N8 C24 C25 121.4(6) . . ?
C25 C24 H24 119.3 . . ?
C24 C25 H25 120.6 . . ?
C26 C25 C24 118.8(5) . . ?
C26 C25 H25 120.6 . . ?
C25 C26 H26 119.1 . . ?
C25 C26 C27 121.8(5) . . ?
C27 C26 H26 119.1 . . ?
C23 C27 C28 123.9(5) . . ?
C26 C27 C23 115.3(5) . . ?
C26 C27 C28 120.8(5) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N9 C29 C30 177.7(8) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N10 C31 C32 178.9(8) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
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 2.8769(4) . ?
Bi1 I2 3.0556(4) . ?
Bi1 I3 2.9079(4) . ?
Bi1 I4 3.3519(4) 2_667 ?
Bi1 I4 3.3430(4) . ?
Bi1 I5 3.0965(4) . ?
Bi2 I2 3.2406(4) 2_667 ?
Bi2 I4 3.3063(4) . ?
Bi2 I5 3.2175(4) . ?
Bi2 I6 2.9306(5) . ?
Bi2 I7 2.9088(5) . ?
Bi2 I8 2.9681(4) . ?
I9 I10 2.7602(8) . ?
N1 C1 1.380(6) . ?
N1 C15 1.287(6) . ?
N2 C2 1.391(6) . ?
N2 C3 1.383(6) . ?
N2 C8 1.385(6) . ?
N3 C1 1.368(6) . ?
N3 C8 1.321(6) . ?
N4 C9 1.365(7) . ?
N4 C10 1.342(7) . ?
N5 HN5 0.86(2) . ?
N5 C15 1.390(6) . ?
N5 C22 1.382(6) . ?
N6 HN6 0.8800 . ?
N6 C16 1.363(7) . ?
N6 C17 1.331(7) . ?
N7 HN7A 0.8800 . ?
N7 HN7B 0.8800 . ?
N7 C22 1.207(6) . ?
N8 C23 1.332(7) . ?
N8 C24 1.346(7) . ?
C1 C2 1.409(7) . ?
C2 C6 1.429(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.349(8) . ?
C4 H4A 0.9500 . ?
C4 C5 1.429(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.355(7) . ?
C6 C7 1.503(8) . ?
C7 H7C 0.9800 . ?
C7 H7D 0.9800 . ?
C7 H7E 0.9800 . ?
C8 C9 1.454(7) . ?
C9 C13 1.405(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.370(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(10) . ?
C12 H12 0.9500 . ?
C12 C13 1.398(8) . ?
C13 C14 1.493(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.475(7) . ?
C16 C20 1.399(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.366(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(9) . ?
C19 H19 0.9500 . ?
C19 C20 1.410(8) . ?
C20 C21 1.488(8) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.497(7) . ?
C23 C27 1.409(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.393(8) . ?
C25 H25 0.9500 . ?
C25 C26 1.360(9) . ?
C26 H26 0.9500 . ?
C26 C27 1.395(8) . ?
C27 C28 1.504(8) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N9 C29 1.142(8) . ?
C29 C30 1.454(9) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N10 C31 1.129(10) . ?
C31 C32 1.457(10) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
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 N2 -176.9(4) . . . . ?
N1 C1 C2 C6 0.4(9) . . . . ?
N1 C15 C16 N6 128.6(5) . . . . ?
N1 C15 C16 C20 -46.2(7) . . . . ?
N2 C2 C6 C5 2.9(7) . . . . ?
N2 C2 C6 C7 -176.6(4) . . . . ?
N2 C3 C4 C5 0.8(8) . . . . ?
N2 C8 C9 N4 48.5(7) . . . . ?
N2 C8 C9 C13 -131.3(5) . . . . ?
N3 C1 C2 N2 -0.7(5) . . . . ?
N3 C1 C2 C6 176.7(5) . . . . ?
N3 C8 C9 N4 -131.2(5) . . . . ?
N3 C8 C9 C13 49.0(8) . . . . ?
N4 C9 C13 C12 -1.5(7) . . . . ?
N4 C9 C13 C14 -179.1(5) . . . . ?
N4 C10 C11 C12 -0.4(9) . . . . ?
N5 C15 C16 N6 -44.1(7) . . . . ?
N5 C15 C16 C20 141.1(5) . . . . ?
N5 C22 C23 N8 18.8(6) . . . . ?
N5 C22 C23 C27 -157.6(5) . . . . ?
N6 C16 C20 C19 -2.9(7) . . . . ?
N6 C16 C20 C21 174.3(5) . . . . ?
N6 C17 C18 C19 -2.5(9) . . . . ?
N7 C22 C23 N8 -162.4(5) . . . . ?
N7 C22 C23 C27 21.3(8) . . . . ?
N8 C23 C27 C26 1.6(8) . . . . ?
N8 C23 C27 C28 -175.3(5) . . . . ?
N8 C24 C25 C26 0.4(9) . . . . ?
C1 N1 C15 N5 0.4(8) . . . . ?
C1 N1 C15 C16 -171.7(4) . . . . ?
C1 N3 C8 N2 -0.8(6) . . . . ?
C1 N3 C8 C9 178.9(5) . . . . ?
C1 C2 C6 C5 -174.2(5) . . . . ?
C1 C2 C6 C7 6.3(9) . . . . ?
C2 N2 C3 C4 1.1(7) . . . . ?
C2 N2 C8 N3 0.4(5) . . . . ?
C2 N2 C8 C9 -179.4(4) . . . . ?
C3 N2 C2 C1 175.0(4) . . . . ?
C3 N2 C2 C6 -2.9(7) . . . . ?
C3 N2 C8 N3 -173.8(5) . . . . ?
C3 N2 C8 C9 6.4(8) . . . . ?
C3 C4 C5 C6 -0.8(8) . . . . ?
C4 C5 C6 C2 -1.1(8) . . . . ?
C4 C5 C6 C7 178.3(5) . . . . ?
C8 N2 C2 C1 0.2(5) . . . . ?
C8 N2 C2 C6 -177.7(4) . . . . ?
C8 N2 C3 C4 174.5(5) . . . . ?
C8 N3 C1 N1 177.1(5) . . . . ?
C8 N3 C1 C2 0.9(6) . . . . ?
C8 C9 C13 C12 178.3(5) . . . . ?
C8 C9 C13 C14 0.7(8) . . . . ?
C9 N4 C10 C11 -1.1(9) . . . . ?
C10 N4 C9 C8 -177.7(5) . . . . ?
C10 N4 C9 C13 2.1(8) . . . . ?
C10 C11 C12 C13 0.9(9) . . . . ?
C11 C12 C13 C9 0.0(8) . . . . ?
C11 C12 C13 C14 177.7(5) . . . . ?
C15 N1 C1 N3 4.7(8) . . . . ?
C15 N1 C1 C2 -179.7(5) . . . . ?
C15 N5 C22 N7 -4.9(8) . . . . ?
C15 N5 C22 C23 173.9(4) . . . . ?
C15 C16 C20 C19 171.8(5) . . . . ?
C15 C16 C20 C21 -11.0(8) . . . . ?
C16 N6 C17 C18 1.2(9) . . . . ?
C17 N6 C16 C15 -173.5(5) . . . . ?
C17 N6 C16 C20 1.6(8) . . . . ?
C17 C18 C19 C20 1.1(9) . . . . ?
C18 C19 C20 C16 1.6(8) . . . . ?
C18 C19 C20 C21 -175.5(5) . . . . ?
C22 N5 C15 N1 158.8(5) . . . . ?
C22 N5 C15 C16 -29.2(7) . . . . ?
C22 C23 C27 C26 177.6(5) . . . . ?
C22 C23 C27 C28 0.6(8) . . . . ?
C23 N8 C24 C25 2.0(8) . . . . ?
C24 N8 C23 C22 -179.3(5) . . . . ?
C24 N8 C23 C27 -3.1(8) . . . . ?
C24 C25 C26 C27 -1.9(9) . . . . ?
C25 C26 C27 C23 1.0(8) . . . . ?
C25 C26 C27 C28 178.0(5) . . . . ?
