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_7245374
_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(I3), C12 H10 N4 S, C12 H8 N4 S'
_chemical_formula_sum            'C24 H18 I6 N8 S2'
_chemical_formula_weight         1243.98
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 99.309(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7763(6)
_cell_length_b                   25.918(2)
_cell_length_c                   17.0369(13)
_cell_measurement_reflns_used    9328
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.42
_cell_volume                     3388.5(5)
_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      100.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0496
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            52923
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_min         2.423
_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    5.653
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4307
_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    2.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.511
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.116
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         1.056
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         6943
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0217
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0149P)^2^+6.1469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0505
_refine_ls_wR_factor_ref         0.0531
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6369
_reflns_number_total             6943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00904h2.cif
_cod_data_source_block           mo_d8_4091_18feb20_ajp1_0m_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_database_code               7245374
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.560
_shelx_estimated_absorpt_t_min   0.160
_olex2_refinement_description
;
1. Restrained distances
 S1A-N3A \\sim S1B-N3B
 with sigma of 0.01
 C1-S1B \\sim C7-S1A
 with sigma of 0.01
 C13-N7A \\sim C19-N7B
 with sigma of 0.01
 C13-S2B \\sim C19-S2A
 with sigma of 0.01
 S2A-N7A \\sim S2B-N7B
 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
S1A \\sim N3A: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C19 \\sim N7B: within 2A with sigma of 0.007 and sigma for terminal atoms of
0.014 within 2A
C13 \\sim S2B: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
3. Others
 Sof(S1B)=Sof(N3B)=1-FVAR(1)
 Sof(S1A)=Sof(N3A)=FVAR(1)
 Sof(S2B)=Sof(N7B)=1-FVAR(2)
 Sof(S2A)=Sof(N7A)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_res_checksum              70750
_olex2_submission_special_instructions 'No special instructions were received'