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_7245364
_publ_section_title
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 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         'I3, C10 H9 N6, 0.75(C2 H3 N)'
_chemical_formula_sum            'C11.5 H11.25 I3 N6.75'
_chemical_formula_weight         624.72
_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            8
_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, 2015<i>b</i>)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015<i>a</i>)'
_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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0165P)^2^+9.9264P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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 

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C46 H45 I12 N27'
_cod_original_formula_weight         2498.89
_cod_original_formula_moiety         '4(I3), 4(C10 H9 N6), 3(C2 H3 N)'
_cod_original_formula_units_Z            2
_cod_database_code               7245364
_shelx_shelxl_version_number     2018/3
_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)
;
_shelx_res_checksum              10423
_olex2_submission_special_instructions 'No special instructions were received'