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#$Date: 2021-09-11 04:56:19 +0300 (Sat, 11 Sep 2021) $
#$Revision: 269097 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022445.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022445
loop_
_publ_author_name
'Peloquin, Andrew J.'
'Ragusa, Arianna C.'
'McMillen, Colin D.'
'Pennington, William T.'
_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 H16 N4 S2, C2 I4'
_chemical_formula_moiety         'C6 H16 N4 S2, C2 I4'
_chemical_formula_sum            'C5 H8 I4 N2 S'
_chemical_formula_weight         635.79
_chemical_name_systematic
;
1,3-Dimethylthiourea--1,1,2,2-tetraiodoethene (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 107.2430(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.3783(3)
_cell_length_b                   4.32943(5)
_cell_length_c                   14.67541(19)
_cell_measurement_reflns_used    37161
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      29.1490
_cell_measurement_theta_min      1.4410
_cell_volume                     1357.93(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010) and OLEX2 (Dolomanov et al.,
2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.103
_diffrn_reflns_theta_min         1.906
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    9.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    3.110
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.137
_refine_diff_density_max         0.877
_refine_diff_density_min         -1.006
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1797
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.234
_refine_ls_R_factor_all          0.0154
_refine_ls_R_factor_gt           0.0151
_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/[σ²(Fo²)+(0.0137P)²+3.9553P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0365
_refine_ls_wR_factor_ref         0.0366
_reflns_number_gt                1776
_reflns_number_total             1797
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vp3021sup1.cif
_cod_data_source_block           8
_cod_database_code               2022445
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.240
_shelx_estimated_absorpt_t_max   0.362
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.36502(2) 0.37698(4) 0.52220(2) 0.01435(5) Uani d 1 . .
I I2 0.26092(2) 0.51778(4) 0.65643(2) 0.01395(5) Uani d 1 . .
C C1 0.27321(11) 0.3197(6) 0.53236(17) 0.0141(5) Uani d 1 . .
S S1 0.500000 0.500000 0.500000 0.0385(3) Uani d 1 . .
N N1 0.5420(2) 0.0670(13) 0.6392(4) 0.0225(10) Uani d 0.5 A -1
H H1N1 0.529(3) -0.058(14) 0.592(4) 0.027 Uiso d 0.5 . .
N N2 0.5657(2) 0.5580(13) 0.6987(4) 0.0256(11) Uani d 0.5 A -1
H H1N2 0.584(3) 0.466(16) 0.752(3) 0.031 Uiso d 0.5 . .
C C2 0.5394(2) 0.3734(14) 0.6253(4) 0.0205(11) Uani d 0.5 A -1
C C3 0.5765(7) -0.081(4) 0.7279(8) 0.034(3) Uani d 0.5 A -1
H H3A 0.571723 -0.300528 0.721438 0.051 Uiso calc 0.5 A -1
H H3B 0.620053 -0.028150 0.742732 0.051 Uiso calc 0.5 A -1
H H3C 0.560676 -0.010635 0.778399 0.051 Uiso calc 0.5 A -1
C C4 0.5669(6) 0.897(4) 0.6936(8) 0.035(3) Uani d 0.5 A -1
H H4A 0.588450 0.978598 0.755401 0.053 Uiso calc 0.5 A -1
H H4B 0.588231 0.958376 0.648646 0.053 Uiso calc 0.5 A -1
H H4C 0.524827 0.973899 0.673502 0.053 Uiso calc 0.5 A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
I2 C1 I1 . . 113.06(11) ?
C1 C1 I1 7_556 . 124.9(2) ?
C1 C1 I2 7_556 . 122.0(2) ?
C2 N1 H1N1 . . 121(5) ?
C2 N1 C3 . . 124.0(7) ?
C3 N1 H1N1 . . 114(5) ?
C2 N2 H1N2 . . 116(5) ?
C2 N2 C4 . . 124.7(7) ?
C4 N2 H1N2 . . 120(5) ?
N1 C2 S1 . . 115.2(4) ?
N2 C2 S1 . . 125.9(5) ?
N2 C2 N1 . . 118.9(5) ?
N1 C3 H3A . . 109.5 ?
N1 C3 H3B . . 109.5 ?
N1 C3 H3C . . 109.5 ?
H3A C3 H3B . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N2 C4 H4A . . 109.5 ?
N2 C4 H4B . . 109.5 ?
N2 C4 H4C . . 109.5 ?
H4A C4 H4B . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C1 . 2.118(2) ?
I2 C1 . 2.103(2) ?
C1 C1 7_556 1.327(5) ?
S1 C2 . 1.871(6) ?
N1 H1N1 . 0.86(2) ?
N1 C2 . 1.341(8) ?
N1 C3 . 1.451(12) ?
N2 H1N2 . 0.86(2) ?
N2 C2 . 1.330(7) ?
N2 C4 . 1.468(17) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N1 C2 S1 . . . . 172.7(9) ?
C3 N1 C2 N2 . . . . -5.5(12) ?
C4 N2 C2 S1 . . . . 1.5(11) ?
C4 N2 C2 N1 . . . . 179.4(8) ?

_cod_database_fobs_code 2022445
