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_7245370
_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         '4(I3), 2(C5 H5 N3 S), 2(C15 H13 N9), C2 H3 N'
_chemical_formula_sum            'C42 H39 I12 N25 S2'
_chemical_formula_weight         2480.90
_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                78.700(2)
_cell_angle_beta                 89.492(2)
_cell_angle_gamma                77.193(2)
_cell_formula_units_Z            1
_cell_length_a                   8.0951(4)
_cell_length_b                   12.8879(7)
_cell_length_c                   16.9574(9)
_cell_measurement_reflns_used    9752
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.349
_cell_measurement_theta_min      2.582
_cell_volume                     1690.59(15)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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  0.0304
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            86268
_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         27.875
_diffrn_reflns_theta_min         2.246
_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    5.609
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0566 before and 0.0471 after correction.
The Ratio of minimum to maximum transmission is 0.8735.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1134
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.071
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         8055
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0163
_refine_ls_R_factor_gt           0.0139
_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^)+(0.0062P)^2^+1.6614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0277
_refine_ls_wR_factor_ref         0.0286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7488
_reflns_number_total             8055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00904h2.cif
_cod_data_source_block           mo_d8_5050_14mar21_ajp5_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               7245370
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.692
_shelx_estimated_absorpt_t_min   0.405
_olex2_refinement_description
;
1. Restrained distances
 HN5-N5 = HN1-N1 = HN7A-N7 = HN7B-N7
 0.86 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
N13 \\sim C21 \\sim C22: within 2A with sigma of 0.003 and sigma for terminal
atoms of 0.006 within 2A
3. Others
 Fixed Sof: N13(0.5) C21(0.5) C22(0.5) H21A(0.5) H21B(0.5) H21C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C18(H17), C19(H18), C20(H19), C3(H7), C4(H8A), C5(H9), C8(H14), C9(H13),
 C10(H12), C13(H4), C14(H3), C15(H2)
4.b X=CH2 refined with riding coordinates:
 N10(H1,HN10)
4.c Idealised Me refined as rotating group:
 C22(H21A,H21B,H21C)
;
_shelx_res_checksum              54114
_olex2_submission_special_instructions 'No special instructions were received'