Isolation of unique heterocycles formed from pyridine-thiocarboxamides as diiodine, iodide, or polyiodide salts
Peloquin, Andrew J.; McMillen, Colin; Pennington, William; CrystEngComm  (2022) –; doi:10.1039/D2CE00904H

data_7245369
_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
'2(Bi6 I22), 4.5(I2), 3(C18 H15 N6), 3(C2 H3 N), 2(H2 O)'
_chemical_formula_sum            'C60 H58 Bi12 I53 N21 O2'
_chemical_formula_weight         10338.73
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-04-18
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-27 deposited with the CCDC.	2022-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                92.184(2)
_cell_angle_beta                 93.977(2)
_cell_angle_gamma                106.355(2)
_cell_formula_units_Z            1
_cell_length_a                   11.3588(6)
_cell_length_b                   11.5129(6)
_cell_length_c                   34.8748(17)
_cell_measurement_reflns_used    9712
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.35
_cell_volume                     4357.7(4)
_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    'Mercury (Macrae <i>et al.</i>, 2008)'
_computing_publication_material  'Olex2 1.5 (Dolomanov <i>et al.</i>, 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015<i>b</i>)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015<i>a</i>)'
_diffrn_ambient_temperature      100.01
_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       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            86802
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.127
_diffrn_source                   'Incoatec I\mS'
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    21.491
_exptl_absorpt_correction_T_max  0.0206
_exptl_absorpt_correction_T_min  0.0048
_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    3.940
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             4386
_exptl_crystal_size_max          0.071
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         2.226
_refine_diff_density_min         -1.452
_refine_diff_density_rms         0.274
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.208(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1349
_refine_ls_number_reflns         34387
_refine_ls_number_restraints     71
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0458
_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/[\s^2^(Fo^2^)+(0.0488P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                27768
_reflns_number_total             34387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00904h2.cif
_cod_data_source_block           mo_d8_4601_21sep20_ajp3_0m_b
_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               7245369
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.537
_shelx_estimated_absorpt_t_min   0.311
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.792(6)
 0.208(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 O1-H1O1 = O1-H2O1
 0.84 with sigma of 0.01
 O2-H1O2 = O2-H2O2
 0.84 with sigma of 0.01
 H1O1-H2O1
 1.33 with sigma of 0.02
 H1O2-H2O2
 1.33 with sigma of 0.02
 H1O2-N12 \\sim H1O2-N13
 with sigma of 0.02
 H2O2-N12 \\sim H2O2-N13
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
N18 \\sim C43 \\sim C45: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
N21 \\sim C59 \\sim C60: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
N19 \\sim C49 \\sim C50 \\sim C51 \\sim C52: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 2A
C57 \\sim C58: within 2A with sigma of 0.02 and sigma for terminal atoms of
0.04 within 2A
N20 \\sim C55 \\sim C56: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
5.a Aromatic/amide H refined with riding coordinates:
 N4(HN4), N5(HN5), N6(HN6), C3(H3), C4(H4A), C5(H5A), C6(H6A), C8(H8), C9(H9),
 C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18), N11(HN11),
 N12(HN12), N13(HN13), C23(H23), C24(H24), C25(H25), C26(H26), C29(H29),
 C30(H30), C31(H31), C32(H32), C35(H35), C36(H36), C37(H37), C38(H38), N18(HN8),
  N19(HN19), N20(HN20), C43(H43), C44(H44), C45(H45), C46(H46), C49(H49),
 C50(H50), C51(H51), C52(H52), C55(H55), C56(H56), C57(H57), C58(H58)
5.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C40(H40A,H40B,H40C), C60(H60A,H60B,H60C)
;
_shelx_res_checksum              43057
_olex2_submission_special_instructions 'No special instructions were received'