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_7245372
_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         '10.144(I2), 2.856(C2 H3 N), C36 H26 Fe N12'
_chemical_formula_sum            'C41.71 H34.57 Fe I20.29 N14.86'
_chemical_formula_weight         3374.55
_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
_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                103.605(2)
_cell_angle_beta                 96.773(2)
_cell_angle_gamma                111.876(2)
_cell_formula_units_Z            2
_cell_length_a                   13.3176(6)
_cell_length_b                   16.6001(7)
_cell_length_c                   19.8556(8)
_cell_measurement_reflns_used    9599
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.58
_cell_volume                     3855.0(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      100.00
_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  0.0405
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            145950
_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         26.372
_diffrn_reflns_theta_min         1.985
_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    8.359
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4265
_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    2.907
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2980
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.208
_exptl_crystal_size_min          0.092
_exptl_transmission_factor_max   'not measured'
_exptl_transmission_factor_min   'not measured'
_refine_diff_density_max         4.522
_refine_diff_density_min         -3.633
_refine_diff_density_rms         0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     759
_refine_ls_number_reflns         15754
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0167P)^2^+50.5551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14074
_reflns_number_total             15754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00904h2.cif
_cod_data_source_block           mo_d8_4596_20sep20_ajp4_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_original_cell_volume        3854.9(3)
_cod_database_code               7245372
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.513
_shelx_estimated_absorpt_t_min   0.193
_olex2_refinement_description
;
1. Restrained distances
 HN6-N6
 0.86 with sigma of 0.02
 HN12-N12
 0.86 with sigma of 0.02
 C43-C44
 1.45 with sigma of 0.02
 N16-C44
 0.001 with sigma of 2.6
2. Uiso/Uaniso restraints and constraints
C43 \\sim C44: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
N15 \\sim C41 \\sim C42: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
Uanis(C41) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C42) \\sim Ueq, Uanis(C44) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N16) = Uanis(C43)
3. Others
 1*[Sof(I22A)+Sof(I23A)]+1*[Sof(N15)+Sof(C41)+Sof(C42)+Sof(H42A)+Sof(H42B)+
 Sof(H42C)]+1*[Sof(N16)+Sof(C43)+Sof(C44)+Sof(H44A)+Sof(H44B)+Sof(H44C)]=1 with
 esd of 0.0001
 Sof(I22A)=Sof(I23A)=FVAR(1)
 Sof(N15)=Sof(C41)=Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(H42C)=FVAR(2)
 Sof(N16)=Sof(C43)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(3)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6A), C9(H9), C10(H10), C11(H11), C12(H12A),
 C15(H15), C16(H16), C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24),
  C27(H27), C28(H28), C29(H29), C30(H30), C33(H33), C34(H34), C35(H35), C36(H36)
4.b Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C44(H44A,H44B,H44C), C38(H38A,H38B,H38C), C40(H40A,H40B,
 H40C)
;
_shelx_res_checksum              73215
_olex2_submission_special_instructions 'No special instructions were received'