#------------------------------------------------------------------------------
#$Date: 2022-08-24 01:33:25 +0300 (Wed, 24 Aug 2022) $
#$Revision: 277360 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/53/7245371.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_7245371
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         '3(I5), 2(C2 H3 N), C18 H15 N6'
_chemical_formula_sum            'C22 H21 I15 N8'
_chemical_formula_weight         2300.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 94.853(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3464(2)
_cell_length_b                   26.9370(4)
_cell_length_c                   24.3715(5)
_cell_measurement_reflns_used    117800
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.371
_cell_measurement_theta_min      1.512
_cell_volume                     4805.59(18)
_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(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            117800
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.512
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    9.686
_exptl_absorpt_correction_T_max  0.732
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.58a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4016
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.071
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         3.074
_refine_diff_density_min         -2.431
_refine_diff_density_rms         0.170
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         9825
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0260
_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)+(0.0107P)²+17.2779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0454
_refine_ls_wR_factor_ref         0.0477
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8421
_reflns_number_total             9825
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00904h2.cif
_cod_data_source_block           nicotin_a
_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_original_cell_volume        4805.58(18)
_cod_database_code               7245371
_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   0.546
_shelx_estimated_absorpt_t_min   0.224
_olex2_refinement_description
;
1. Restrained distances
 HN6-N6 = HN4-N4 = HN5-N5
 0.85 with sigma of 0.02
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5A), C6(H6A), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.13475(5) 0.95792(2) 0.43209(2) 0.03392(9) Uani 1 1 d . . . . .
I2 I 0.31819(5) 0.94896(2) 0.53533(2) 0.02845(9) Uani 1 1 d . . . . .
I3 I 0.50730(5) 0.94663(2) 0.66035(2) 0.02736(8) Uani 1 1 d . . . . .
I4 I 0.47906(4) 0.83421(2) 0.68503(2) 0.02464(8) Uani 1 1 d . . . . .
I5 I 0.44726(5) 0.73109(2) 0.69936(2) 0.02931(9) Uani 1 1 d . . . . .
N8 N 0.7812(7) 0.85651(17) 0.5516(2) 0.0375(12) Uani 1 1 d . . . . .
C21 C 0.8718(8) 0.8759(2) 0.5858(3) 0.0331(14) Uani 1 1 d . . . . .
C22 C 0.9801(7) 0.8965(2) 0.6326(2) 0.0349(14) Uani 1 1 d . . . . .
H22A H 0.923093 0.889086 0.665708 0.052 Uiso 1 1 calc R U . . .
H22B H 0.988802 0.931832 0.628450 0.052 Uiso 1 1 calc R U . . .
H22C H 1.100238 0.882240 0.634879 0.052 Uiso 1 1 calc R U . . .
I6 I -0.12719(5) 0.51319(2) 0.78739(2) 0.02905(9) Uani 1 1 d . . . . .
I7 I 0.16652(5) 0.54909(2) 0.73616(2) 0.02520(8) Uani 1 1 d . . . . .
I8 I 0.51325(5) 0.59317(2) 0.67372(2) 0.02715(8) Uani 1 1 d . . . . .
I9 I 0.31308(4) 0.61289(2) 0.56180(2) 0.02406(8) Uani 1 1 d . . . . .
I10 I 0.12607(5) 0.63510(2) 0.45841(2) 0.03093(9) Uani 1 1 d . . . . .
I11 I 0.25921(5) 0.77001(2) 0.55218(2) 0.03353(9) Uani 1 1 d . . . . .
I12 I 0.13104(4) 0.79739(2) 0.44613(2) 0.02209(8) Uani 1 1 d . . . . .
I13 I 0.00432(5) 0.82214(2) 0.32321(2) 0.02556(8) Uani 1 1 d . . . . .
I14 I -0.04157(4) 0.71005(2) 0.30787(2) 0.02334(8) Uani 1 1 d . . . . .
I15 I -0.08421(4) 0.60585(2) 0.29595(2) 0.02530(8) Uani 1 1 d . . . . .
N1 N 0.6547(5) 0.67006(14) 0.47460(16) 0.0177(9) Uani 1 1 d . . . . .
N2 N 0.6752(5) 0.75796(14) 0.48317(16) 0.0177(9) Uani 1 1 d . . . . .
N3 N 0.5579(5) 0.72223(14) 0.39838(16) 0.0157(9) Uani 1 1 d . . . . .
N4 N 0.7972(5) 0.74962(16) 0.58877(18) 0.0222(9) Uani 1 1 d D . . . .
HN4 H 0.765(7) 0.7756(13) 0.570(2) 0.036(17) Uiso 1 1 d D . . . .
N5 N 0.6367(6) 0.84935(15) 0.43984(19) 0.0228(10) Uani 1 1 d D . . . .
HN5 H 0.681(8) 0.845(2) 0.4729(12) 0.06(2) Uiso 1 1 d D . . . .
N6 N 0.5811(6) 0.58931(15) 0.41195(18) 0.0214(9) Uani 1 1 d D . . . .
HN6 H 0.630(7) 0.589(2) 0.4447(11) 0.034(17) Uiso 1 1 d D . . . .
C1 C 0.6967(6) 0.71183(17) 0.50288(19) 0.0166(10) Uani 1 1 d . . . . .
C2 C 0.6073(6) 0.76064(17) 0.4308(2) 0.0179(11) Uani 1 1 d . . . . .
C3 C 0.5854(6) 0.67800(17) 0.4231(2) 0.0167(10) Uani 1 1 d . . . . .
C4 C 0.7748(6) 0.70702(18) 0.5598(2) 0.0189(11) Uani 1 1 d . . . . .
C5 C 0.8754(7) 0.7512(2) 0.6400(2) 0.0265(12) Uani 1 1 d . . . . .
H5A H 0.887949 0.781437 0.658462 0.032 Uiso 1 1 calc R U . . .
C6 C 0.9380(7) 0.7082(2) 0.6659(2) 0.0284(13) Uani 1 1 d . . . . .
H6A H 0.993932 0.709110 0.701588 0.034 Uiso 1 1 calc R U . . .
C7 C 0.9161(7) 0.6636(2) 0.6378(2) 0.0259(12) Uani 1 1 d . . . . .
H7 H 0.956702 0.634175 0.654579 0.031 Uiso 1 1 calc R U . . .
C8 C 0.8329(6) 0.66323(19) 0.5845(2) 0.0219(11) Uani 1 1 d . . . . .
H8 H 0.816707 0.633412 0.565433 0.026 Uiso 1 1 calc R U . . .
C9 C 0.5845(6) 0.81081(17) 0.4064(2) 0.0173(10) Uani 1 1 d . . . . .
C10 C 0.6233(7) 0.89649(19) 0.4231(2) 0.0282(13) Uani 1 1 d . . . . .
H10 H 0.661503 0.922167 0.446900 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5518(7) 0.9066(2) 0.3699(2) 0.0318(14) Uani 1 1 d . . . . .
H11 H 0.539690 0.939277 0.357803 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4989(7) 0.8684(2) 0.3351(2) 0.0284(13) Uani 1 1 d . . . . .
H12 H 0.451347 0.874954 0.299212 0.034 Uiso 1 1 calc R U . . .
C13 C 0.5166(6) 0.81950(18) 0.3536(2) 0.0213(11) Uani 1 1 d . . . . .
H13 H 0.482607 0.793214 0.330186 0.026 Uiso 1 1 calc R U . . .
C14 C 0.5353(6) 0.63384(17) 0.38948(19) 0.0175(10) Uani 1 1 d . . . . .
C15 C 0.5423(7) 0.54620(18) 0.3857(2) 0.0246(12) Uani 1 1 d . . . . .
H15 H 0.575449 0.516106 0.402396 0.029 Uiso 1 1 calc R U . . .
C16 C 0.4528(7) 0.54735(19) 0.3339(2) 0.0252(12) Uani 1 1 d . . . . .
H16 H 0.425252 0.517850 0.315141 0.030 Uiso 1 1 calc R U . . .
C17 C 0.4036(6) 0.59229(18) 0.3095(2) 0.0217(11) Uani 1 1 d . . . . .
H17 H 0.342374 0.593214 0.274505 0.026 Uiso 1 1 calc R U . . .
C18 C 0.4462(6) 0.63570(18) 0.3377(2) 0.0180(11) Uani 1 1 d . . . . .
H18 H 0.414749 0.666169 0.321597 0.022 Uiso 1 1 calc R U . . .
N7 N 0.7535(7) 0.54046(18) 0.5074(2) 0.0380(12) Uani 1 1 d . . . . .
C19 C 0.8310(7) 0.52495(19) 0.5452(2) 0.0271(12) Uani 1 1 d . . . . .
C20 C 0.9323(8) 0.5059(2) 0.5947(2) 0.0344(14) Uani 1 1 d . . . . .
H20A H 0.873448 0.516275 0.626455 0.052 Uiso 1 1 calc R U . . .
H20B H 1.054746 0.518683 0.596942 0.052 Uiso 1 1 calc R U . . .
H20C H 0.935485 0.470349 0.593199 0.052 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 174.480(16) . . ?
I4 I3 I2 99.851(13) . . ?
I5 I4 I3 175.922(16) . . ?
N8 C21 C22 174.1(6) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
I6 I7 I8 179.095(16) . . ?
I9 I8 I7 98.243(13) . . ?
I10 I9 I8 177.859(16) . . ?
I11 I12 I13 175.794(16) . . ?
I14 I13 I12 85.847(12) . . ?
I15 I14 I13 178.850(16) . . ?
C3 N1 C1 113.8(4) . . ?
C2 N2 C1 114.7(4) . . ?
C2 N3 C3 113.6(4) . . ?
C4 N4 HN4 114(4) . . ?
C5 N4 HN4 123(4) . . ?
C5 N4 C4 122.8(5) . . ?
C9 N5 HN5 123(4) . . ?
C10 N5 HN5 115(4) . . ?
C10 N5 C9 122.4(5) . . ?
C14 N6 HN6 117(4) . . ?
C15 N6 HN6 120(4) . . ?
C15 N6 C14 122.6(5) . . ?
N1 C1 C4 117.9(4) . . ?
N2 C1 N1 125.4(4) . . ?
N2 C1 C4 116.7(4) . . ?
N2 C2 N3 125.9(4) . . ?
N2 C2 C9 117.0(4) . . ?
N3 C2 C9 117.1(4) . . ?
N1 C3 N3 126.6(4) . . ?
N1 C3 C14 116.9(4) . . ?
N3 C3 C14 116.5(4) . . ?
N4 C4 C1 116.2(4) . . ?
N4 C4 C8 118.8(5) . . ?
C8 C4 C1 125.0(5) . . ?
N4 C5 H5A 119.9 . . ?
N4 C5 C6 120.1(5) . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 H6A 120.6 . . ?
C5 C6 C7 118.8(5) . . ?
C7 C6 H6A 120.6 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(5) . . ?
C8 C7 H7 120.2 . . ?
C4 C8 C7 119.8(5) . . ?
C4 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
N5 C9 C2 116.2(4) . . ?
N5 C9 C13 120.0(4) . . ?
C13 C9 C2 123.8(4) . . ?
N5 C10 H10 120.5 . . ?
N5 C10 C11 119.0(5) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.9(5) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.7(5) . . ?
C13 C12 H12 120.2 . . ?
C9 C13 C12 119.1(5) . . ?
C9 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N6 C14 C3 116.8(4) . . ?
N6 C14 C18 119.2(4) . . ?
C18 C14 C3 124.0(4) . . ?
N6 C15 H15 120.5 . . ?
N6 C15 C16 118.9(5) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.1(5) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.2(5) . . ?
C18 C17 H17 120.4 . . ?
C14 C18 C17 119.8(5) . . ?
C14 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
N7 C19 C20 178.7(6) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 2.7626(5) . ?
I2 I3 3.2406(5) . ?
I3 I4 3.0976(5) . ?
I4 I5 2.8118(5) . ?
N8 C21 1.147(7) . ?
C21 C22 1.446(8) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
I6 I7 2.7578(5) . ?
I7 I8 3.2969(5) . ?
I8 I9 3.0341(5) . ?
I9 I10 2.8301(5) . ?
I11 I12 2.7747(5) . ?
I12 I13 3.1327(5) . ?
I13 I14 3.0576(5) . ?
I14 I15 2.8364(5) . ?
N1 C1 1.342(6) . ?
N1 C3 1.332(6) . ?
N2 C1 1.337(6) . ?
N2 C2 1.333(6) . ?
N3 C2 1.333(6) . ?
N3 C3 1.342(6) . ?
N4 HN4 0.855(19) . ?
N4 C4 1.350(6) . ?
N4 C5 1.331(6) . ?
N5 HN5 0.85(2) . ?
N5 C9 1.355(6) . ?
N5 C10 1.334(6) . ?
N6 HN6 0.848(19) . ?
N6 C14 1.349(6) . ?
N6 C15 1.344(6) . ?
C1 C4 1.462(7) . ?
C2 C9 1.480(6) . ?
C3 C14 1.473(6) . ?
C4 C8 1.375(6) . ?
C5 H5A 0.9300 . ?
C5 C6 1.380(7) . ?
C6 H6A 0.9300 . ?
C6 C7 1.384(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.390(7) . ?
C8 H8 0.9300 . ?
C9 C13 1.361(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.394(7) . ?
C13 H13 0.9300 . ?
C14 C18 1.374(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.378(7) . ?
C18 H18 0.9300 . ?
N7 C19 1.122(6) . ?
C19 C20 1.455(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C22 H22A I15 0.96 3.18 4.048(6) 150.9 4_676 yes
C22 H22B I6 0.96 3.11 3.807(5) 130.5 2_656 yes
C22 H22C I4 0.96 3.22 4.134(6) 160.9 1_655 yes
N4 HN4 N8 0.855(19) 2.23(3) 3.018(6) 153(5) . yes
N4 HN4 N2 0.855(19) 2.22(5) 2.662(6) 112(4) . yes
N5 HN5 N8 0.85(2) 2.02(3) 2.845(7) 164(6) . yes
N6 HN6 N7 0.848(19) 2.15(4) 2.872(6) 142(5) . yes
C6 H6A I13 0.93 3.08 3.910(5) 150.1 4_676 yes
C11 H11 I3 0.93 3.12 4.038(5) 169.6 3_676 yes
C13 H13 I5 0.93 3.24 3.990(5) 138.7 4_575 yes
C16 H16 I6 0.93 3.29 3.990(5) 133.9 3_566 yes
C16 H16 I8 0.93 3.03 3.799(5) 140.7 3_666 yes
C20 H20C I10 0.96 3.12 4.025(6) 156.9 3_666 yes
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 C4 N4 -173.2(4) . . . . ?
N1 C1 C4 C8 9.8(7) . . . . ?
N1 C3 C14 N6 -6.5(6) . . . . ?
N1 C3 C14 C18 173.4(4) . . . . ?
N2 C1 C4 N4 7.5(6) . . . . ?
N2 C1 C4 C8 -169.5(4) . . . . ?
N2 C2 C9 N5 0.6(6) . . . . ?
N2 C2 C9 C13 -179.8(4) . . . . ?
N3 C2 C9 N5 -179.5(4) . . . . ?
N3 C2 C9 C13 0.1(7) . . . . ?
N3 C3 C14 N6 172.9(4) . . . . ?
N3 C3 C14 C18 -7.2(7) . . . . ?
N4 C4 C8 C7 -1.2(7) . . . . ?
N4 C5 C6 C7 -0.7(8) . . . . ?
N5 C9 C13 C12 -1.2(7) . . . . ?
N5 C10 C11 C12 -1.1(8) . . . . ?
N6 C14 C18 C17 0.5(7) . . . . ?
N6 C15 C16 C17 -0.2(7) . . . . ?
C1 N1 C3 N3 0.8(6) . . . . ?
C1 N1 C3 C14 -179.8(4) . . . . ?
C1 N2 C2 N3 1.5(6) . . . . ?
C1 N2 C2 C9 -178.7(4) . . . . ?
C1 C4 C8 C7 175.8(4) . . . . ?
C2 N2 C1 N1 -0.6(6) . . . . ?
C2 N2 C1 C4 178.6(4) . . . . ?
C2 N3 C3 N1 -0.1(6) . . . . ?
C2 N3 C3 C14 -179.5(4) . . . . ?
C2 C9 C13 C12 179.2(4) . . . . ?
C3 N1 C1 N2 -0.4(6) . . . . ?
C3 N1 C1 C4 -179.6(4) . . . . ?
C3 N3 C2 N2 -1.2(6) . . . . ?
C3 N3 C2 C9 179.0(4) . . . . ?
C3 C14 C18 C17 -179.4(4) . . . . ?
C4 N4 C5 C6 0.1(7) . . . . ?
C5 N4 C4 C1 -176.3(4) . . . . ?
C5 N4 C4 C8 0.9(7) . . . . ?
C5 C6 C7 C8 0.3(7) . . . . ?
C6 C7 C8 C4 0.6(7) . . . . ?
C9 N5 C10 C11 0.7(7) . . . . ?
C10 N5 C9 C2 -179.9(4) . . . . ?
C10 N5 C9 C13 0.5(7) . . . . ?
C10 C11 C12 C13 0.3(8) . . . . ?
C11 C12 C13 C9 0.8(7) . . . . ?
C14 N6 C15 C16 0.1(7) . . . . ?
C15 N6 C14 C3 179.6(4) . . . . ?
C15 N6 C14 C18 -0.3(7) . . . . ?
C15 C16 C17 C18 0.4(7) . . . . ?
C16 C17 C18 C14 -0.5(7) . . . . ?
