#------------------------------------------------------------------------------
#$Date: 2022-08-24 01:33:25 +0300 (Wed, 24 Aug 2022) $
#$Revision: 277360 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/53/7245364.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_7245364
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         '4(I3), 4(C10 H9 N6), 3(C2 H3 N)'
_chemical_formula_sum            'C46 H45 I12 N27'
_chemical_formula_weight         2498.89
_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                93.901(2)
_cell_angle_beta                 101.189(2)
_cell_angle_gamma                91.407(2)
_cell_formula_units_Z            2
_cell_length_a                   13.5105(5)
_cell_length_b                   14.6827(7)
_cell_length_c                   17.4311(8)
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      2.57
_cell_volume                     3381.7(3)
_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      100.0
_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  0.0510
_diffrn_reflns_av_unetI/netI     0.0239
_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       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            143131
_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         27.877
_diffrn_reflns_theta_min         2.113
_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    5.550
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5653
_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    2.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2292
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.097
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         1.465
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     817
_refine_ls_number_reflns         16112
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0241
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0165P)²+9.9264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0567
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13684
_reflns_number_total             16112
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00904h2.cif
_cod_data_source_block           mo_d8_5046_14mar21_ajp1_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               7245364
_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   0.615
_shelx_estimated_absorpt_t_min   0.422
_olex2_refinement_description
;
1. Restrained distances
 HN3-N3
 0.86 with sigma of 0.02
 HN7B-N7
 0.86 with sigma of 0.02
 HN15-N15
 0.86 with sigma of 0.02
 HN19-N19
 0.86 with sigma of 0.02
 N19-H2
 0.86 with sigma of 0.02
 HN7A-N7
 0.86 with sigma of 0.02
 HN9-N9
 0.86 with sigma of 0.02
 HN13-N13
 0.86 with sigma of 0.02
 H1-N13
 0.86 with sigma of 0.02
 N21-HN21
 0.86 with sigma of 0.02
2. Restrained planarity
 N3, HN3, C3, C4
 with sigma of 0.1
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C4(H4), C7(H7), C8(H8), C9(H9), C44(H44), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C46(H46), C20(H20), C21(H21A), C22(H22),
 C25(H25), C26(H26), C27(H27), C30(H30), C31(H31), C32(H32), C35(H35), C36(H36),
  C37(H37)
3.b Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C41(H41A,H41B,H41C), C43(H43A,H43B,H43C)
;
_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
I1 I 0.86100(2) 0.06915(2) 0.60307(2) 0.01906(5) Uani 1 1 d . . . . .
I2 I 0.86361(2) 0.04408(2) 0.43604(2) 0.01749(5) Uani 1 1 d . . . . .
I3 I 0.87008(2) 0.01960(2) 0.26874(2) 0.01989(5) Uani 1 1 d . . . . .
I4 I 0.58652(2) 0.14605(2) 0.46354(2) 0.02356(5) Uani 1 1 d . . . . .
I5 I 0.59745(2) 0.13966(2) 0.29500(2) 0.02064(5) Uani 1 1 d . . . . .
I6 I 0.61490(2) 0.13089(2) 0.13210(2) 0.02455(6) Uani 1 1 d . . . . .
I7 I 0.31097(2) 0.54608(2) 0.08248(2) 0.02664(6) Uani 1 1 d . . . . .
I8 I 0.34318(2) 0.74518(2) 0.08372(2) 0.02286(5) Uani 1 1 d . . . . .
I9 I 0.37707(2) 0.94233(2) 0.09695(2) 0.03036(6) Uani 1 1 d . . . . .
I10 I 1.05096(2) 0.65150(2) -0.03293(2) 0.02442(6) Uani 1 1 d . . . . .
I11 I 0.86502(2) 0.72654(2) -0.11850(2) 0.02158(5) Uani 1 1 d . . . . .
I12 I 0.67838(2) 0.79566(2) -0.20718(2) 0.02627(6) Uani 1 1 d . . . . .
N1 N 0.8449(3) 0.3018(2) 0.5276(2) 0.0257(7) Uani 1 1 d . . . . .
HN1B H 0.843(3) 0.255(3) 0.544(3) 0.018(11) Uiso 1 1 d . . . . .
HN1A H 0.838(4) 0.305(3) 0.478(3) 0.033(13) Uiso 1 1 d . . . . .
N2 N 0.9021(2) 0.4762(2) 0.68344(18) 0.0170(6) Uani 1 1 d . . . . .
N3 N 0.8916(2) 0.3516(2) 0.7922(2) 0.0215(7) Uani 1 1 d D . . . .
HN3 H 0.885(3) 0.309(3) 0.822(3) 0.042(15) Uiso 1 1 d D . . . .
N4 N 0.8792(2) 0.4598(2) 0.55250(19) 0.0189(6) Uani 1 1 d . . . . .
N5 N 0.9234(2) 0.6707(2) 0.67955(19) 0.0207(6) Uani 1 1 d . . . . .
N6 N 0.9165(2) 0.7433(2) 0.53368(19) 0.0194(6) Uani 1 1 d . . . . .
C1 C 0.8682(3) 0.3757(2) 0.5774(2) 0.0183(7) Uani 1 1 d . . . . .
C2 C 0.8821(3) 0.3814(2) 0.6609(2) 0.0181(7) Uani 1 1 d . . . . .
C3 C 0.8774(3) 0.3215(2) 0.7168(2) 0.0192(7) Uani 1 1 d . . . . .
H3A H 0.863975 0.258247 0.701969 0.023 Uiso 1 1 calc R U . . .
C4 C 0.9130(3) 0.4434(3) 0.8155(2) 0.0221(8) Uani 1 1 d . . . . .
H4 H 0.923670 0.462934 0.869642 0.027 Uiso 1 1 calc R U . . .
C5 C 0.8990(3) 0.5188(2) 0.6171(2) 0.0168(7) Uani 1 1 d . . . . .
C6 C 0.9110(3) 0.6174(2) 0.6125(2) 0.0165(7) Uani 1 1 d . . . . .
C7 C 0.9082(3) 0.6532(2) 0.5399(2) 0.0192(7) Uani 1 1 d . . . . .
H7 H 0.900245 0.612748 0.494069 0.023 Uiso 1 1 calc R U . . .
C8 C 0.9283(3) 0.7965(2) 0.6007(2) 0.0210(8) Uani 1 1 d . . . . .
H8 H 0.934832 0.860844 0.598927 0.025 Uiso 1 1 calc R U . . .
C9 C 0.9314(3) 0.7607(2) 0.6722(2) 0.0220(8) Uani 1 1 d . . . . .
H9 H 0.939492 0.801392 0.717975 0.026 Uiso 1 1 calc R U . . .
C44 C 0.9190(3) 0.5050(2) 0.7633(2) 0.0195(7) Uani 1 1 d . . . . .
H44 H 0.934453 0.567542 0.780131 0.023 Uiso 1 1 calc R U . . .
N7 N 0.5895(3) 0.3822(2) 0.4092(2) 0.0273(7) Uani 1 1 d D . . . .
HN7B H 0.584(4) 0.3271(17) 0.421(3) 0.034(13) Uiso 1 1 d D . . . .
HN7A H 0.581(3) 0.390(3) 0.3600(12) 0.020(11) Uiso 1 1 d D . . . .
N8 N 0.6455(2) 0.5502(2) 0.57036(19) 0.0211(7) Uani 1 1 d . . . . .
N9 N 0.6370(3) 0.4181(2) 0.6731(2) 0.0265(7) Uani 1 1 d D . . . .
HN9 H 0.629(4) 0.376(3) 0.704(3) 0.046(15) Uiso 1 1 d D . . . .
N10 N 0.6208(2) 0.5408(2) 0.4391(2) 0.0217(7) Uani 1 1 d . . . . .
N11 N 0.6803(2) 0.7437(2) 0.57440(19) 0.0233(7) Uani 1 1 d . . . . .
N12 N 0.6494(3) 0.8269(2) 0.4325(2) 0.0257(7) Uani 1 1 d . . . . .
C10 C 0.6122(3) 0.4544(3) 0.4610(2) 0.0213(8) Uani 1 1 d . . . . .
C11 C 0.6260(3) 0.4561(2) 0.5440(2) 0.0211(8) Uani 1 1 d . . . . .
C12 C 0.6224(3) 0.3924(3) 0.5963(2) 0.0235(8) Uani 1 1 d . . . . .
H12 H 0.609585 0.329805 0.578571 0.028 Uiso 1 1 calc R U . . .
C13 C 0.6553(3) 0.5092(3) 0.7000(2) 0.0271(9) Uani 1 1 d . . . . .
H13 H 0.664834 0.525563 0.754721 0.033 Uiso 1 1 calc R U . . .
C14 C 0.6542(3) 0.6954(3) 0.5054(2) 0.0201(7) Uani 1 1 d . . . . .
C15 C 0.6401(3) 0.7364(3) 0.4346(2) 0.0246(8) Uani 1 1 d . . . . .
H15 H 0.623555 0.699174 0.386849 0.030 Uiso 1 1 calc R U . . .
C16 C 0.6734(3) 0.8759(3) 0.5013(2) 0.0249(8) Uani 1 1 d . . . . .
H16 H 0.679863 0.940601 0.502158 0.030 Uiso 1 1 calc R U . . .
C17 C 0.6892(3) 0.8344(3) 0.5715(2) 0.0249(8) Uani 1 1 d . . . . .
H17 H 0.707082 0.871533 0.619197 0.030 Uiso 1 1 calc R U . . .
C45 C 0.6409(3) 0.5961(2) 0.5051(2) 0.0192(7) Uani 1 1 d . . . . .
C46 C 0.6600(3) 0.5747(3) 0.6506(2) 0.0242(8) Uani 1 1 d . . . . .
H46 H 0.673008 0.636760 0.669999 0.029 Uiso 1 1 calc R U . . .
N13 N 0.6321(3) 0.8794(2) 0.2698(2) 0.0270(7) Uani 1 1 d D . . . .
HN13 H 0.640(4) 0.871(3) 0.3199(13) 0.037(14) Uiso 1 1 d D . . . .
H1 H 0.649(4) 0.931(2) 0.255(3) 0.043(15) Uiso 1 1 d D . . . .
N14 N 0.6164(2) 0.7082(2) 0.11259(19) 0.0199(6) Uani 1 1 d . . . . .
N15 N 0.6246(3) 0.8383(3) 0.0091(2) 0.0305(8) Uani 1 1 d D . . . .
HN15 H 0.625(4) 0.881(3) -0.023(3) 0.048(16) Uiso 1 1 d D . . . .
N16 N 0.6171(2) 0.7202(2) 0.24127(19) 0.0197(6) Uani 1 1 d . . . . .
N17 N 0.6012(2) 0.5123(2) 0.1113(2) 0.0226(7) Uani 1 1 d . . . . .
N18 N 0.5725(3) 0.4356(2) 0.2485(2) 0.0239(7) Uani 1 1 d . . . . .
C18 C 0.6257(3) 0.8057(3) 0.2191(2) 0.0222(8) Uani 1 1 d . . . . .
C19 C 0.6256(3) 0.8026(3) 0.1372(2) 0.0217(8) Uani 1 1 d . . . . .
C20 C 0.6290(3) 0.8658(3) 0.0838(3) 0.0260(8) Uani 1 1 d . . . . .
H20 H 0.634515 0.929162 0.100080 0.031 Uiso 1 1 calc R U . . .
C21 C 0.6144(3) 0.7461(3) -0.0163(3) 0.0292(9) Uani 1 1 d . . . . .
H21A H 0.610120 0.728538 -0.070349 0.035 Uiso 1 1 calc R U . . .
C22 C 0.6105(3) 0.6819(3) 0.0333(2) 0.0244(8) Uani 1 1 d . . . . .
H22 H 0.603869 0.619159 0.015148 0.029 Uiso 1 1 calc R U . . .
C23 C 0.6110(3) 0.6632(2) 0.1766(2) 0.0194(7) Uani 1 1 d . . . . .
C24 C 0.5987(3) 0.5642(2) 0.1773(2) 0.0175(7) Uani 1 1 d . . . . .
C25 C 0.5861(3) 0.5259(2) 0.2460(2) 0.0216(8) Uani 1 1 d . . . . .
H25 H 0.587202 0.564734 0.292095 0.026 Uiso 1 1 calc R U . . .
C26 C 0.5716(3) 0.3843(3) 0.1819(2) 0.0243(8) Uani 1 1 d . . . . .
H26 H 0.559590 0.320162 0.180706 0.029 Uiso 1 1 calc R U . . .
C27 C 0.5878(3) 0.4225(3) 0.1145(2) 0.0252(8) Uani 1 1 d . . . . .
H27 H 0.589293 0.383301 0.069147 0.030 Uiso 1 1 calc R U . . .
N19 N 0.8895(3) 0.7877(2) 0.3666(2) 0.0241(7) Uani 1 1 d D . . . .
HN19 H 0.897(3) 0.784(3) 0.4152(12) 0.024(12) Uiso 1 1 d D . . . .
H2 H 0.901(3) 0.8390(18) 0.351(3) 0.027(12) Uiso 1 1 d D . . . .
N20 N 0.8512(2) 0.61046(19) 0.21265(18) 0.0171(6) Uani 1 1 d . . . . .
N21 N 0.8648(2) 0.7351(2) 0.10461(19) 0.0212(7) Uani 1 1 d D . . . .
HN21 H 0.867(4) 0.773(3) 0.069(2) 0.046(16) Uiso 1 1 d D . . . .
N22 N 0.8640(2) 0.6281(2) 0.34301(19) 0.0178(6) Uani 1 1 d . . . . .
N23 N 0.8312(2) 0.4160(2) 0.21735(19) 0.0203(6) Uani 1 1 d . . . . .
N24 N 0.8309(2) 0.3443(2) 0.3618(2) 0.0213(7) Uani 1 1 d . . . . .
C28 C 0.8741(3) 0.7125(2) 0.3180(2) 0.0167(7) Uani 1 1 d . . . . .
C29 C 0.8668(3) 0.7056(2) 0.2350(2) 0.0165(7) Uani 1 1 d . . . . .
C30 C 0.8739(3) 0.7653(2) 0.1794(2) 0.0194(7) Uani 1 1 d . . . . .
H30 H 0.885404 0.828701 0.194197 0.023 Uiso 1 1 calc R U . . .
C31 C 0.8476(3) 0.6427(2) 0.0815(2) 0.0197(7) Uani 1 1 d . . . . .
H31 H 0.840834 0.622916 0.027605 0.024 Uiso 1 1 calc R U . . .
C32 C 0.8405(3) 0.5811(2) 0.1334(2) 0.0190(7) Uani 1 1 d . . . . .
H32 H 0.828299 0.518164 0.116643 0.023 Uiso 1 1 calc R U . . .
C33 C 0.8503(3) 0.5685(2) 0.2790(2) 0.0167(7) Uani 1 1 d . . . . .
C34 C 0.8390(3) 0.4702(2) 0.2838(2) 0.0173(7) Uani 1 1 d . . . . .
C35 C 0.8381(3) 0.4345(2) 0.3554(2) 0.0192(7) Uani 1 1 d . . . . .
H35 H 0.842720 0.474975 0.401010 0.023 Uiso 1 1 calc R U . . .
C36 C 0.8232(3) 0.2907(2) 0.2958(2) 0.0202(7) Uani 1 1 d . . . . .
H36 H 0.817440 0.226330 0.297817 0.024 Uiso 1 1 calc R U . . .
C37 C 0.8236(3) 0.3265(2) 0.2243(2) 0.0239(8) Uani 1 1 d . . . . .
H37 H 0.818235 0.285796 0.178776 0.029 Uiso 1 1 calc R U . . .
N25 N 0.8953(3) 0.1674(2) 0.8340(2) 0.0327(8) Uani 1 1 d . . . . .
C38 C 0.8857(3) 0.0911(3) 0.8293(2) 0.0241(8) Uani 1 1 d . . . . .
C39 C 0.8736(4) -0.0088(3) 0.8237(3) 0.0341(10) Uani 1 1 d . . . . .
H39A H 0.921820 -0.035268 0.793907 0.051 Uiso 1 1 calc R U . . .
H39B H 0.804705 -0.027257 0.796945 0.051 Uiso 1 1 calc R U . . .
H39C H 0.886404 -0.030611 0.876484 0.051 Uiso 1 1 calc R U . . .
N26 N 0.6295(3) 0.2302(3) 0.6996(2) 0.0419(10) Uani 1 1 d . . . . .
C40 C 0.6131(3) 0.1540(3) 0.6873(2) 0.0294(9) Uani 1 1 d . . . . .
C41 C 0.5916(4) 0.0564(3) 0.6702(3) 0.0331(10) Uani 1 1 d . . . . .
H41A H 0.641196 0.030545 0.641461 0.050 Uiso 1 1 calc R U . . .
H41B H 0.523667 0.046073 0.638198 0.050 Uiso 1 1 calc R U . . .
H41C H 0.595605 0.026911 0.719402 0.050 Uiso 1 1 calc R U . . .
N27 N 0.8750(3) 0.9207(2) 0.0519(2) 0.0326(8) Uani 1 1 d . . . . .
C42 C 0.8775(3) 0.9974(3) 0.0501(2) 0.0258(8) Uani 1 1 d . . . . .
C43 C 0.8815(3) 1.0976(3) 0.0496(3) 0.0316(9) Uani 1 1 d . . . . .
H43A H 0.823757 1.116883 0.011775 0.047 Uiso 1 1 calc R U . . .
H43B H 0.944380 1.117548 0.034524 0.047 Uiso 1 1 calc R U . . .
H43C H 0.879160 1.124951 0.101997 0.047 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'
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 I2 I3 178.989(11) . . ?
I6 I5 I4 178.036(12) . . ?
I9 I8 I7 175.952(13) . . ?
I12 I11 I10 178.090(12) . . ?
HN1B N1 HN1A 119(5) . . ?
C1 N1 HN1B 119(3) . . ?
C1 N1 HN1A 122(3) . . ?
C5 N2 C2 106.9(3) . . ?
C5 N2 C44 134.5(3) . . ?
C44 N2 C2 118.6(3) . . ?
C3 N3 HN3 112(4) . . ?
C3 N3 C4 121.1(3) . . ?
C4 N3 HN3 127(4) . . ?
C1 N4 C5 106.8(3) . . ?
C9 N5 C6 115.6(3) . . ?
C7 N6 C8 116.3(3) . . ?
N1 C1 N4 122.0(4) . . ?
N1 C1 C2 128.1(3) . . ?
N4 C1 C2 109.8(3) . . ?
N2 C2 C1 104.3(3) . . ?
C3 C2 N2 119.7(3) . . ?
C3 C2 C1 135.9(3) . . ?
N3 C3 C2 120.1(3) . . ?
N3 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
N3 C4 H4 119.3 . . ?
C44 C4 N3 121.4(4) . . ?
C44 C4 H4 119.3 . . ?
N2 C5 N4 112.1(3) . . ?
N2 C5 C6 125.6(3) . . ?
N4 C5 C6 122.3(3) . . ?
N5 C6 C5 117.6(3) . . ?
N5 C6 C7 122.3(3) . . ?
C7 C6 C5 120.1(3) . . ?
N6 C7 C6 121.4(3) . . ?
N6 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
N6 C8 H8 119.0 . . ?
N6 C8 C9 122.1(3) . . ?
C9 C8 H8 119.0 . . ?
N5 C9 C8 122.4(3) . . ?
N5 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
N2 C44 H44 120.4 . . ?
C4 C44 N2 119.2(3) . . ?
C4 C44 H44 120.4 . . ?
HN7B N7 HN7A 116(4) . . ?
C10 N7 HN7B 125(3) . . ?
C10 N7 HN7A 119(3) . . ?
C45 N8 C11 106.2(3) . . ?
C45 N8 C46 135.2(3) . . ?
C46 N8 C11 118.5(3) . . ?
C12 N9 HN9 117(4) . . ?
C12 N9 C13 121.0(3) . . ?
C13 N9 HN9 122(4) . . ?
C45 N10 C10 106.9(3) . . ?
C14 N11 C17 115.9(3) . . ?
C16 N12 C15 116.9(4) . . ?
N7 C10 N10 122.6(4) . . ?
N7 C10 C11 127.8(4) . . ?
N10 C10 C11 109.6(3) . . ?
C10 C11 N8 104.7(3) . . ?
C12 C11 N8 120.3(4) . . ?
C12 C11 C10 135.0(4) . . ?
N9 C12 C11 119.7(4) . . ?
N9 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
N9 C13 H13 119.2 . . ?
C46 C13 N9 121.5(4) . . ?
C46 C13 H13 119.2 . . ?
N11 C14 C15 122.1(4) . . ?
N11 C14 C45 118.2(3) . . ?
C15 C14 C45 119.6(3) . . ?
N12 C15 C14 121.4(4) . . ?
N12 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
N12 C16 H16 119.3 . . ?
N12 C16 C17 121.3(4) . . ?
C17 C16 H16 119.3 . . ?
N11 C17 C16 122.4(4) . . ?
N11 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
N8 C45 C14 124.4(3) . . ?
N10 C45 N8 112.6(3) . . ?
N10 C45 C14 123.0(3) . . ?
N8 C46 H46 120.5 . . ?
C13 C46 N8 118.9(4) . . ?
C13 C46 H46 120.5 . . ?
HN13 N13 H1 120(5) . . ?
C18 N13 HN13 118(3) . . ?
C18 N13 H1 118(4) . . ?
C22 N14 C19 118.8(3) . . ?
C23 N14 C19 106.7(3) . . ?
C23 N14 C22 134.5(3) . . ?
C20 N15 HN15 116(4) . . ?
C20 N15 C21 121.2(4) . . ?
C21 N15 HN15 122(4) . . ?
C23 N16 C18 106.9(3) . . ?
C27 N17 C24 116.2(3) . . ?
C26 N18 C25 116.7(3) . . ?
N13 C18 N16 122.2(4) . . ?
N13 C18 C19 128.1(4) . . ?
N16 C18 C19 109.7(3) . . ?
N14 C19 C18 104.5(3) . . ?
C20 C19 N14 120.1(4) . . ?
C20 C19 C18 135.4(4) . . ?
N15 C20 C19 119.5(4) . . ?
N15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
N15 C21 H21A 119.2 . . ?
C22 C21 N15 121.5(4) . . ?
C22 C21 H21A 119.2 . . ?
N14 C22 H22 120.5 . . ?
C21 C22 N14 118.9(4) . . ?
C21 C22 H22 120.5 . . ?
N14 C23 C24 125.0(3) . . ?
N16 C23 N14 112.2(3) . . ?
N16 C23 C24 122.7(3) . . ?
N17 C24 C23 118.4(3) . . ?
N17 C24 C25 121.8(3) . . ?
C25 C24 C23 119.7(3) . . ?
N18 C25 C24 121.4(4) . . ?
N18 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
N18 C26 H26 119.2 . . ?
N18 C26 C27 121.6(4) . . ?
C27 C26 H26 119.2 . . ?
N17 C27 C26 122.2(4) . . ?
N17 C27 H27 118.9 . . ?
C26 C27 H27 118.9 . . ?
HN19 N19 H2 118(4) . . ?
C28 N19 HN19 121(3) . . ?
C28 N19 H2 121(3) . . ?
C32 N20 C29 118.7(3) . . ?
C33 N20 C29 106.6(3) . . ?
C33 N20 C32 134.8(3) . . ?
C30 N21 HN21 120(4) . . ?
C30 N21 C31 120.9(3) . . ?
C31 N21 HN21 119(4) . . ?
C33 N22 C28 107.0(3) . . ?
C37 N23 C34 116.3(3) . . ?
C36 N24 C35 116.7(3) . . ?
N19 C28 N22 122.8(3) . . ?
N19 C28 C29 127.8(3) . . ?
N22 C28 C29 109.4(3) . . ?
N20 C29 C28 104.7(3) . . ?
C30 C29 N20 119.6(3) . . ?
C30 C29 C28 135.7(3) . . ?
N21 C30 C29 120.3(3) . . ?
N21 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
N21 C31 H31 119.3 . . ?
C32 C31 N21 121.4(3) . . ?
C32 C31 H31 119.3 . . ?
N20 C32 H32 120.5 . . ?
C31 C32 N20 119.1(3) . . ?
C31 C32 H32 120.5 . . ?
N20 C33 C34 125.3(3) . . ?
N22 C33 N20 112.3(3) . . ?
N22 C33 C34 122.4(3) . . ?
N23 C34 C33 118.0(3) . . ?
N23 C34 C35 121.6(3) . . ?
C35 C34 C33 120.4(3) . . ?
N24 C35 C34 121.5(3) . . ?
N24 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
N24 C36 H36 119.1 . . ?
N24 C36 C37 121.7(3) . . ?
C37 C36 H36 119.1 . . ?
N23 C37 C36 122.1(4) . . ?
N23 C37 H37 118.9 . . ?
C36 C37 H37 118.9 . . ?
N25 C38 C39 179.5(6) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N26 C40 C41 179.1(5) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N27 C42 C43 178.9(5) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 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
I1 I2 2.9169(4) . ?
I2 I3 2.9325(4) . ?
I4 I5 2.9653(4) . ?
I5 I6 2.8890(4) . ?
I7 I8 2.9429(4) . ?
I8 I9 2.9061(4) . ?
I10 I11 2.9419(4) . ?
I11 I12 2.9333(4) . ?
N1 HN1B 0.75(5) . ?
N1 HN1A 0.86(5) . ?
N1 C1 1.335(5) . ?
N2 C2 1.425(4) . ?
N2 C5 1.345(5) . ?
N2 C44 1.400(5) . ?
N3 HN3 0.851(19) . ?
N3 C3 1.333(5) . ?
N3 C4 1.388(5) . ?
N4 C1 1.350(4) . ?
N4 C5 1.353(5) . ?
N5 C6 1.342(5) . ?
N5 C9 1.340(5) . ?
N6 C7 1.339(4) . ?
N6 C8 1.341(5) . ?
C1 C2 1.426(5) . ?
C2 C3 1.367(5) . ?
C3 H3A 0.9500 . ?
C4 H4 0.9500 . ?
C4 C44 1.338(5) . ?
C5 C6 1.463(5) . ?
C6 C7 1.395(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.378(5) . ?
C9 H9 0.9500 . ?
C44 H44 0.9500 . ?
N7 HN7B 0.855(19) . ?
N7 HN7A 0.859(19) . ?
N7 C10 1.334(5) . ?
N8 C11 1.427(5) . ?
N8 C45 1.353(5) . ?
N8 C46 1.395(5) . ?
N9 HN9 0.861(19) . ?
N9 C12 1.342(5) . ?
N9 C13 1.387(5) . ?
N10 C10 1.357(5) . ?
N10 C45 1.342(5) . ?
N11 C14 1.334(5) . ?
N11 C17 1.339(5) . ?
N12 C15 1.336(5) . ?
N12 C16 1.335(5) . ?
C10 C11 1.421(5) . ?
C11 C12 1.357(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C46 1.343(6) . ?
C14 C15 1.391(5) . ?
C14 C45 1.464(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.386(6) . ?
C17 H17 0.9500 . ?
C46 H46 0.9500 . ?
N13 HN13 0.876(19) . ?
N13 H1 0.854(19) . ?
N13 C18 1.339(5) . ?
N14 C19 1.417(5) . ?
N14 C22 1.396(5) . ?
N14 C23 1.348(5) . ?
N15 HN15 0.864(19) . ?
N15 C20 1.328(6) . ?
N15 C21 1.391(6) . ?
N16 C18 1.347(5) . ?
N16 C23 1.345(5) . ?
N17 C24 1.342(5) . ?
N17 C27 1.334(5) . ?
N18 C25 1.339(5) . ?
N18 C26 1.338(5) . ?
C18 C19 1.426(6) . ?
C19 C20 1.364(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9500 . ?
C21 C22 1.328(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.460(5) . ?
C24 C25 1.394(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.387(6) . ?
C27 H27 0.9500 . ?
N19 HN19 0.840(19) . ?
N19 H2 0.844(19) . ?
N19 C28 1.330(5) . ?
N20 C29 1.424(4) . ?
N20 C32 1.398(5) . ?
N20 C33 1.349(5) . ?
N21 HN21 0.859(19) . ?
N21 C30 1.329(5) . ?
N21 C31 1.389(5) . ?
N22 C28 1.354(4) . ?
N22 C33 1.349(5) . ?
N23 C34 1.346(5) . ?
N23 C37 1.332(5) . ?
N24 C35 1.340(5) . ?
N24 C36 1.334(5) . ?
C28 C29 1.428(5) . ?
C29 C30 1.366(5) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C31 C32 1.338(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.457(5) . ?
C34 C35 1.388(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C36 C37 1.385(6) . ?
C37 H37 0.9500 . ?
N25 C38 1.120(5) . ?
C38 C39 1.467(5) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
N26 C40 1.134(6) . ?
C40 C41 1.453(6) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
N27 C42 1.128(5) . ?
C42 C43 1.471(6) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 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 -178.0(4) . . . . ?
N1 C1 C2 C3 -0.4(7) . . . . ?
N2 C2 C3 N3 -0.1(5) . . . . ?
N2 C5 C6 N5 -2.0(5) . . . . ?
N2 C5 C6 C7 178.8(3) . . . . ?
N3 C4 C44 N2 0.7(6) . . . . ?
N4 C1 C2 N2 0.1(4) . . . . ?
N4 C1 C2 C3 177.7(4) . . . . ?
N4 C5 C6 N5 175.3(3) . . . . ?
N4 C5 C6 C7 -3.9(5) . . . . ?
N5 C6 C7 N6 -0.9(6) . . . . ?
N6 C8 C9 N5 0.4(6) . . . . ?
C1 N4 C5 N2 0.4(4) . . . . ?
C1 N4 C5 C6 -177.2(3) . . . . ?
C1 C2 C3 N3 -177.4(4) . . . . ?
C2 N2 C5 N4 -0.3(4) . . . . ?
C2 N2 C5 C6 177.2(3) . . . . ?
C2 N2 C44 C4 -1.9(5) . . . . ?
C3 N3 C4 C44 0.8(6) . . . . ?
C4 N3 C3 C2 -1.1(5) . . . . ?
C5 N2 C2 C1 0.1(4) . . . . ?
C5 N2 C2 C3 -178.0(3) . . . . ?
C5 N2 C44 C4 177.5(4) . . . . ?
C5 N4 C1 N1 178.0(3) . . . . ?
C5 N4 C1 C2 -0.3(4) . . . . ?
C5 C6 C7 N6 178.3(3) . . . . ?
C6 N5 C9 C8 -0.7(5) . . . . ?
C7 N6 C8 C9 -0.3(5) . . . . ?
C8 N6 C7 C6 0.5(5) . . . . ?
C9 N5 C6 C5 -178.3(3) . . . . ?
C9 N5 C6 C7 0.9(5) . . . . ?
C44 N2 C2 C1 179.7(3) . . . . ?
C44 N2 C2 C3 1.6(5) . . . . ?
C44 N2 C5 N4 -179.8(4) . . . . ?
C44 N2 C5 C6 -2.3(6) . . . . ?
N7 C10 C11 N8 -178.1(4) . . . . ?
N7 C10 C11 C12 0.4(7) . . . . ?
N8 C11 C12 N9 0.2(6) . . . . ?
N9 C13 C46 N8 0.3(6) . . . . ?
N10 C10 C11 N8 -1.0(4) . . . . ?
N10 C10 C11 C12 177.5(4) . . . . ?
N11 C14 C15 N12 -1.9(6) . . . . ?
N11 C14 C45 N8 5.5(5) . . . . ?
N11 C14 C45 N10 -175.8(3) . . . . ?
N12 C16 C17 N11 -0.8(6) . . . . ?
C10 N10 C45 N8 -0.4(4) . . . . ?
C10 N10 C45 C14 -179.2(3) . . . . ?
C10 C11 C12 N9 -178.2(4) . . . . ?
C11 N8 C45 N10 -0.3(4) . . . . ?
C11 N8 C45 C14 178.5(3) . . . . ?
C11 N8 C46 C13 0.1(5) . . . . ?
C12 N9 C13 C46 -0.5(6) . . . . ?
C13 N9 C12 C11 0.3(6) . . . . ?
C14 N11 C17 C16 -0.6(6) . . . . ?
C15 N12 C16 C17 0.8(6) . . . . ?
C15 C14 C45 N8 -174.9(4) . . . . ?
C15 C14 C45 N10 3.7(6) . . . . ?
C16 N12 C15 C14 0.5(6) . . . . ?
C17 N11 C14 C15 1.9(5) . . . . ?
C17 N11 C14 C45 -178.6(3) . . . . ?
C45 N8 C11 C10 0.8(4) . . . . ?
C45 N8 C11 C12 -178.0(3) . . . . ?
C45 N8 C46 C13 176.9(4) . . . . ?
C45 N10 C10 N7 178.1(4) . . . . ?
C45 N10 C10 C11 0.9(4) . . . . ?
C45 C14 C15 N12 178.6(3) . . . . ?
C46 N8 C11 C10 178.4(3) . . . . ?
C46 N8 C11 C12 -0.3(5) . . . . ?
C46 N8 C45 N10 -177.4(4) . . . . ?
C46 N8 C45 C14 1.4(7) . . . . ?
N13 C18 C19 N14 -179.5(4) . . . . ?
N13 C18 C19 C20 -1.8(7) . . . . ?
N14 C19 C20 N15 -0.6(6) . . . . ?
N14 C23 C24 N17 5.9(5) . . . . ?
N14 C23 C24 C25 -175.0(3) . . . . ?
N15 C21 C22 N14 0.3(6) . . . . ?
N16 C18 C19 N14 -0.1(4) . . . . ?
N16 C18 C19 C20 177.6(4) . . . . ?
N16 C23 C24 N17 -174.8(3) . . . . ?
N16 C23 C24 C25 4.3(5) . . . . ?
N17 C24 C25 N18 -2.3(6) . . . . ?
N18 C26 C27 N17 -2.6(6) . . . . ?
C18 N16 C23 N14 0.7(4) . . . . ?
C18 N16 C23 C24 -178.6(3) . . . . ?
C18 C19 C20 N15 -178.0(4) . . . . ?
C19 N14 C22 C21 0.4(5) . . . . ?
C19 N14 C23 N16 -0.8(4) . . . . ?
C19 N14 C23 C24 178.5(3) . . . . ?
C20 N15 C21 C22 -1.2(6) . . . . ?
C21 N15 C20 C19 1.4(6) . . . . ?
C22 N14 C19 C18 177.8(3) . . . . ?
C22 N14 C19 C20 -0.3(5) . . . . ?
C22 N14 C23 N16 -177.5(4) . . . . ?
C22 N14 C23 C24 1.8(6) . . . . ?
C23 N14 C19 C18 0.5(4) . . . . ?
C23 N14 C19 C20 -177.6(3) . . . . ?
C23 N14 C22 C21 176.9(4) . . . . ?
C23 N16 C18 N13 179.1(4) . . . . ?
C23 N16 C18 C19 -0.4(4) . . . . ?
C23 C24 C25 N18 178.6(3) . . . . ?
C24 N17 C27 C26 0.3(6) . . . . ?
C25 N18 C26 C27 2.4(6) . . . . ?
C26 N18 C25 C24 0.0(6) . . . . ?
C27 N17 C24 C23 -178.8(3) . . . . ?
C27 N17 C24 C25 2.1(5) . . . . ?
N19 C28 C29 N20 179.5(4) . . . . ?
N19 C28 C29 C30 1.6(7) . . . . ?
N20 C29 C30 N21 1.0(5) . . . . ?
N20 C33 C34 N23 1.7(5) . . . . ?
N20 C33 C34 C35 -179.4(3) . . . . ?
N21 C31 C32 N20 -0.4(5) . . . . ?
N22 C28 C29 N20 0.2(4) . . . . ?
N22 C28 C29 C30 -177.7(4) . . . . ?
N22 C33 C34 N23 -176.4(3) . . . . ?
N22 C33 C34 C35 2.5(5) . . . . ?
N23 C34 C35 N24 0.9(6) . . . . ?
N24 C36 C37 N23 -0.2(6) . . . . ?
C28 N22 C33 N20 0.1(4) . . . . ?
C28 N22 C33 C34 178.5(3) . . . . ?
C28 C29 C30 N21 178.7(4) . . . . ?
C29 N20 C32 C31 1.6(5) . . . . ?
C29 N20 C33 N22 0.0(4) . . . . ?
C29 N20 C33 C34 -178.3(3) . . . . ?
C30 N21 C31 C32 -0.5(6) . . . . ?
C31 N21 C30 C29 0.2(5) . . . . ?
C32 N20 C29 C28 179.8(3) . . . . ?
C32 N20 C29 C30 -1.9(5) . . . . ?
C32 N20 C33 N22 -179.8(4) . . . . ?
C32 N20 C33 C34 1.9(6) . . . . ?
C33 N20 C29 C28 -0.1(4) . . . . ?
C33 N20 C29 C30 178.2(3) . . . . ?
C33 N20 C32 C31 -178.6(4) . . . . ?
C33 N22 C28 N19 -179.5(3) . . . . ?
C33 N22 C28 C29 -0.2(4) . . . . ?
C33 C34 C35 N24 -177.9(3) . . . . ?
C34 N23 C37 C36 0.3(5) . . . . ?
C35 N24 C36 C37 0.5(5) . . . . ?
C36 N24 C35 C34 -0.8(5) . . . . ?
C37 N23 C34 C33 178.3(3) . . . . ?
C37 N23 C34 C35 -0.6(5) . . . . ?
