#------------------------------------------------------------------------------
#$Date: 2021-09-11 04:56:19 +0300 (Sat, 11 Sep 2021) $
#$Revision: 269097 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/24/2022444.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_2022444
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 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 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      99.99
_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       'φ and ω 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/[σ²(Fo²)+(0.0027P)²+0.5036P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            vp3021sup1.cif
_cod_data_source_block           7
_cod_database_code               2022444
_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   0.443
_shelx_estimated_absorpt_t_max   0.540
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.75725(2) 0.31998(2) 0.81611(2) 0.01463(3) Uani d 1 . .
I I2 0.79515(2) 0.87867(2) 0.45987(2) 0.01644(3) Uani d 1 . .
I I3 0.72964(2) 0.29766(2) 0.30857(2) 0.01354(3) Uani d 1 . .
F F1 0.79845(14) 0.65146(12) 0.69756(9) 0.0170(2) Uani d 1 . .
F F2 0.75836(15) 0.63852(12) 0.30796(9) 0.0192(2) Uani d 1 . .
F F3 0.70683(15) 0.21127(12) 0.58317(9) 0.0173(2) Uani d 1 . .
C C1 0.7551(2) 0.4277(2) 0.64448(15) 0.0130(3) Uani d 1 . .
C C2 0.7765(2) 0.5763(2) 0.61403(15) 0.0133(3) Uani d 1 . .
C C3 0.7750(2) 0.65157(19) 0.50197(15) 0.0135(3) Uani d 1 . .
C C4 0.7571(2) 0.5695(2) 0.41807(15) 0.0133(3) Uani d 1 . .
C C5 0.7379(2) 0.4196(2) 0.44187(15) 0.0127(3) Uani d 1 . .
C C6 0.7335(2) 0.35391(19) 0.55622(15) 0.0132(3) Uani d 1 . .
S S1 0.24620(6) 0.85328(5) 0.91900(4) 0.01561(9) Uani d 1 . .
N N2 0.4476(2) 1.05856(19) 0.85184(13) 0.0156(3) Uani d 1 . .
H H1N1 0.459(3) 1.144(3) 0.8489(19) 0.020(6) Uiso d 1 . .
N N1 0.1924(2) 1.13121(18) 0.97550(14) 0.0164(3) Uani d 1 . .
H H1N2 0.099(3) 1.113(3) 1.0041(19) 0.019(6) Uiso d 1 . .
C C9 0.5780(2) 0.9580(2) 0.77948(15) 0.0171(4) Uani d 1 . .
H H7A 0.535590 0.978718 0.701895 0.026 Uiso calc 1 . .
H H7B 0.585126 0.850100 0.812051 0.026 Uiso calc 1 . .
H H7C 0.701019 0.977451 0.775811 0.026 Uiso calc 1 . .
C C7 0.2992(2) 1.0268(2) 0.91426(15) 0.0142(3) Uani d 1 . .
C C8 0.2193(3) 1.2827(2) 0.97788(17) 0.0197(4) Uani d 1 . .
H H9A 0.199510 1.345672 0.902228 0.030 Uiso calc 1 . .
H H9B 0.346003 1.272022 0.997090 0.030 Uiso calc 1 . .
H H9C 0.130395 1.332740 1.035916 0.030 Uiso calc 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'
F F 0.0171 0.0103 '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
C2 C1 I1 . . 121.34(13) ?
C2 C1 C6 . . 116.81(16) ?
C6 C1 I1 . . 121.85(13) ?
F1 C2 C1 . . 118.46(15) ?
F1 C2 C3 . . 118.46(15) ?
C3 C2 C1 . . 123.08(16) ?
C2 C3 I2 . . 122.17(13) ?
C2 C3 C4 . . 116.88(16) ?
C4 C3 I2 . . 120.95(13) ?
F2 C4 C3 . . 118.33(15) ?
F2 C4 C5 . . 118.43(15) ?
C3 C4 C5 . . 123.24(16) ?
C4 C5 I3 . . 120.86(13) ?
C6 C5 I3 . . 122.43(12) ?
C6 C5 C4 . . 116.64(15) ?
F3 C6 C1 . . 118.35(15) ?
F3 C6 C5 . . 118.38(15) ?
C5 C6 C1 . . 123.27(16) ?
C9 N2 H1N1 . . 117.6(16) ?
C7 N2 H1N1 . . 116.3(16) ?
C7 N2 C9 . . 125.76(16) ?
C7 N1 H1N2 . . 115.5(16) ?
C7 N1 C8 . . 125.52(16) ?
C8 N1 H1N2 . . 118.2(17) ?
N2 C9 H7A . . 109.5 ?
N2 C9 H7B . . 109.5 ?
N2 C9 H7C . . 109.5 ?
H7A C9 H7B . . 109.5 ?
H7A C9 H7C . . 109.5 ?
H7B C9 H7C . . 109.5 ?
N2 C7 S1 . . 121.44(14) ?
N1 C7 S1 . . 119.86(14) ?
N1 C7 N2 . . 118.69(17) ?
N1 C8 H9A . . 109.5 ?
N1 C8 H9B . . 109.5 ?
N1 C8 H9C . . 109.5 ?
H9A C8 H9B . . 109.5 ?
H9A C8 H9C . . 109.5 ?
H9B C8 H9C . . 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 . 2.0975(17) ?
I2 C3 . 2.0821(17) ?
I3 C5 . 2.1007(17) ?
F1 C2 . 1.3470(19) ?
F2 C4 . 1.346(2) ?
F3 C6 . 1.3445(19) ?
C1 C2 . 1.385(2) ?
C1 C6 . 1.386(2) ?
C2 C3 . 1.383(2) ?
C3 C4 . 1.384(2) ?
C4 C5 . 1.386(2) ?
C5 C6 . 1.382(2) ?
S1 C7 . 1.7200(18) ?
N2 H1N1 . 0.80(2) ?
N2 C9 . 1.457(2) ?
N2 C7 . 1.330(2) ?
N1 H1N2 . 0.78(2) ?
N1 C7 . 1.328(2) ?
N1 C8 . 1.453(2) ?
C9 H7A . 0.9800 ?
C9 H7B . 0.9800 ?
C9 H7C . 0.9800 ?
C8 H9A . 0.9800 ?
C8 H9B . 0.9800 ?
C8 H9C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H1N1 I1 1_565 0.80(2) 3.04(2) 3.6907(16) 140.8(19)
N1 H1N2 S1 2_577 0.78(2) 2.60(2) 3.3493(17) 162(2)
C9 H7A I2 2_676 0.98 3.17 4.0382(19) 148.1
C9 H7B F1 . 0.98 2.54 3.090(2) 115.4
C8 H9A F2 2_676 0.98 2.46 3.331(2) 148.3
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
I1 C1 C2 F1 . . . . -0.2(2) ?
I1 C1 C2 C3 . . . . -179.69(13) ?
I1 C1 C6 F3 . . . . 2.4(2) ?
I1 C1 C6 C5 . . . . -177.70(13) ?
I2 C3 C4 F2 . . . . 1.9(2) ?
I2 C3 C4 C5 . . . . -178.13(13) ?
I3 C5 C6 F3 . . . . -5.9(2) ?
I3 C5 C6 C1 . . . . 174.17(13) ?
F1 C2 C3 I2 . . . . -2.4(2) ?
F1 C2 C3 C4 . . . . 178.36(15) ?
F2 C4 C5 I3 . . . . 4.2(2) ?
F2 C4 C5 C6 . . . . -178.76(15) ?
C1 C2 C3 I2 . . . . 177.08(13) ?
C1 C2 C3 C4 . . . . -2.1(3) ?
C2 C1 C6 F3 . . . . -178.02(15) ?
C2 C1 C6 C5 . . . . 1.9(3) ?
C2 C3 C4 F2 . . . . -178.87(15) ?
C2 C3 C4 C5 . . . . 1.1(3) ?
C3 C4 C5 I3 . . . . -175.80(13) ?
C3 C4 C5 C6 . . . . 1.3(3) ?
C4 C5 C6 F3 . . . . 177.09(15) ?
C4 C5 C6 C1 . . . . -2.8(3) ?
C6 C1 C2 F1 . . . . -179.79(15) ?
C6 C1 C2 C3 . . . . 0.7(3) ?
C9 N2 C7 S1 . . . . 1.6(2) ?
C9 N2 C7 N1 . . . . -179.53(16) ?
C8 N1 C7 S1 . . . . -178.90(14) ?
C8 N1 C7 N2 . . . . 2.3(3) ?

_cod_database_fobs_code 2022444
