The reaction of thiourea and 1,3-dimethylthiourea towards organoiodines: oxidative bond formation and halogen bonding
Peloquin, Andrew J.; Ragusa, Arianna C.; McMillen, Colin D.; Pennington, William T.; Acta Crystallographica Section C 77 (2021) –; doi:10.1107/S205322962100869X

data_2022444
_publ_section_title
;
 The reaction of thiourea and 1,3-dimethylthiourea towards organoiodines:
 oxidative bond formation and halogen bonding
;
_journal_coeditor_code           VP3021
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322962100869X
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C6 F3 I3, C3 H8 N2 S'
_chemical_formula_moiety         'C6 F3 I3, C3 H8 N2 S'
_chemical_formula_sum            'C9 H8 F3 I3 N2 S'
_chemical_formula_weight         613.93
_chemical_name_systematic
;
1,3-Dimethylthiourea--1,3,5-trifluoro-2,4,6-triiodobenzene (1/1)
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                79.871(3)
_cell_angle_beta                 83.011(3)
_cell_angle_gamma                74.410(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5014(6)
_cell_length_b                   9.1065(8)
_cell_length_c                   11.8534(10)
_cell_measurement_reflns_used    9841
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.35
_cell_volume                     765.41(11)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>, 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010) and OLEX2 (Dolomanov <i>et al.</i>,
2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_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  0.0235
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19222
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.433
_diffrn_reflns_theta_min         2.348
_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    6.277
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.112
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.258
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0108
_refine_ls_R_factor_gt           0.0105
_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^)+(0.0027P)^2^+0.5036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0242
_refine_ls_wR_factor_ref         0.0244
_reflns_number_gt                3075
_reflns_number_total             3136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vp3021sup1.cif
_cod_data_source_block           7
_cod_database_code               2022444
_shelx_estimated_absorpt_t_min   0.443
_shelx_estimated_absorpt_t_max   0.540
_shelx_hkl_checksum              37034
_shelx_res_checksum              44667
_cod_database_fobs_code 2022444