#------------------------------------------------------------------------------
#$Date: 2021-02-05 16:53:19 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261799 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022287.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_2022287
loop_
_publ_author_name
'Rosiak, Damian'
'Okuniewski, Andrzej'
'Chojnacki, Jarosław'
_publ_section_title
;
 The influence of the type of halogen substituent and its position on the
 molecular conformation, intermolecular interactions and crystal packing
 for a series of 1-benzoyl-3-(halogenophenyl)thioureas
;
_journal_coeditor_code           WP3011
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              11
_journal_page_last               19
_journal_paper_doi               10.1107/S2053229620015594
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C14 H11 I N2 O S'
_chemical_formula_moiety         'C14 H11 I N2 O S'
_chemical_formula_sum            'C14 H11 I N2 O S'
_chemical_formula_weight         382.21
_chemical_name_common            1-Benzoyl-3-m-iodophenylthiourea
_chemical_name_systematic
;
1-Benzoyl-3-(3-iodophenyl)thiourea
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.404(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.5639(5)
_cell_length_b                   15.375(3)
_cell_length_c                   19.355(2)
_cell_measurement_reflns_used    2158
_cell_measurement_temperature    125
_cell_measurement_theta_max      29.36
_cell_measurement_theta_min      2.53
_cell_volume                     1357.7(3)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2009)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2009)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2009)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      125
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  Stoe_IPDS_2T
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13551
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.487
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.505
_exptl_absorpt_correction_T_max  0.8853
_exptl_absorpt_correction_T_min  0.3932
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
[X-RED32 (Stoe & Cie, 2009), by Gaussian integration,
analogous to Coppens (1970)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.870
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.238
_refine_diff_density_min         -1.275
_refine_ls_abs_structure_details
;
Flack (1983), 2156 Friedel pairs
;
_refine_ls_abs_structure_Flack   0.30(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         5820
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1066P)²+0.9908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1381
_refine_ls_wR_factor_ref         0.1476
_reflns_number_gt                5398
_reflns_number_total             5820
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wp3011sup1.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 2022286--2022290.cif.'
_cod_database_code               2022287
_cod_database_fobs_code          2022287
_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   0.273
_shelx_estimated_absorpt_t_max   0.885
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, 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 I1A 0.87867(10) 0.35387(4) 0.39772(4) 0.0328(2) Uani d 1 . .
I I1 0.14942(12) 0.40415(4) 0.61116(4) 0.0338(2) Uani d 1 . .
S S1 0.7822(7) -0.05110(18) 0.57618(16) 0.0368(6) Uani d 1 . .
S S1A 0.1700(7) 0.80028(19) 0.41313(17) 0.0393(7) Uani d 1 . .
O O1A -0.1126(19) 0.5770(6) 0.5497(4) 0.0330(17) Uani d 1 . .
O O1 1.123(2) 0.1767(5) 0.4527(4) 0.0341(17) Uani d 1 . .
N N2A 0.189(2) 0.6285(7) 0.4449(5) 0.0280(19) Uani d 1 . .
H H2A 0.124794 0.589646 0.474320 0.034 Uiso calc 1 . .
C C12 1.478(3) 0.1371(8) 0.3423(6) 0.030(2) Uani d 1 . .
H H12 1.395714 0.193753 0.345652 0.036 Uiso calc 1 . .
N N2 0.794(2) 0.1221(7) 0.5524(5) 0.0288(19) Uani d 1 . .
H H2 0.868530 0.162280 0.525647 0.035 Uiso calc 1 . .
N N1 1.101(2) 0.0358(6) 0.4888(5) 0.0282(18) Uani d 1 . .
H H1 1.179490 -0.015895 0.482922 0.034 Uiso calc 1 . .
N N1A -0.130(2) 0.7143(6) 0.5053(5) 0.0306(18) Uani d 1 . .
H H1A -0.220421 0.764534 0.508664 0.037 Uiso calc 1 . .
C C25A 0.666(3) 0.5976(7) 0.2925(6) 0.032(2) Uani d 1 . .
H H25A 0.717177 0.625646 0.250752 0.038 Uiso calc 1 . .
C C23 0.299(2) 0.2779(7) 0.6325(6) 0.029(2) Uani d 1 . .
C C21 0.591(2) 0.1540(7) 0.6007(6) 0.027(2) Uani d 1 . .
C C22 0.494(2) 0.2395(7) 0.5876(6) 0.029(2) Uani d 1 . .
H H22 0.560848 0.270554 0.548633 0.035 Uiso calc 1 . .
C C24A 0.788(3) 0.5167(8) 0.3096(7) 0.033(2) Uani d 1 . .
H H24A 0.923610 0.489731 0.279989 0.040 Uiso calc 1 . .
C C10 1.201(3) 0.1003(8) 0.4464(6) 0.029(2) Uani d 1 . .
C C22A 0.508(2) 0.5159(7) 0.4143(6) 0.027(2) Uani d 1 . .
H H22A 0.453406 0.487322 0.455542 0.033 Uiso calc 1 . .
C C26A 0.468(3) 0.6375(9) 0.3372(7) 0.032(3) Uani d 1 . .
H H26A 0.387924 0.692794 0.325606 0.039 Uiso calc 1 . .
C C1 0.891(2) 0.0417(7) 0.5403(6) 0.028(2) Uani d 1 . .
C C11A -0.418(2) 0.6775(7) 0.6071(6) 0.026(2) Uani d 1 . .
C C14 1.788(2) 0.0358(8) 0.2847(6) 0.032(2) Uani d 1 . .
H H14 1.919888 0.023232 0.248821 0.038 Uiso calc 1 . .
C C23A 0.707(2) 0.4762(7) 0.3703(5) 0.027(2) Uani d 1 . .
C C13 1.660(3) 0.1178(9) 0.2890(6) 0.033(2) Uani d 1 . .
H H13 1.698782 0.160457 0.254936 0.040 Uiso calc 1 . .
C C11 1.411(3) 0.0736(7) 0.3919(6) 0.027(2) Uani d 1 . .
C C21A 0.388(3) 0.5969(6) 0.3980(6) 0.029(2) Uani d 1 . .
C C16A -0.573(2) 0.7558(7) 0.6067(6) 0.031(2) Uani d 1 . .
H H16A -0.549717 0.795796 0.569802 0.037 Uiso calc 1 . .
C C24 0.199(3) 0.2334(8) 0.6895(6) 0.033(2) Uani d 1 . .
H H24 0.065033 0.259819 0.719880 0.039 Uiso calc 1 . .
C C15 1.722(3) -0.0272(8) 0.3328(6) 0.035(2) Uani d 1 . .
H H15 1.803195 -0.083840 0.328833 0.042 Uiso calc 1 . .
C C25 0.300(3) 0.1495(7) 0.7013(6) 0.032(2) Uani d 1 . .
H H25 0.236230 0.118764 0.740804 0.039 Uiso calc 1 . .
C C15A -0.760(2) 0.7754(8) 0.6592(6) 0.032(2) Uani d 1 . .
H H15A -0.866389 0.828518 0.658524 0.038 Uiso calc 1 . .
C C13A -0.635(3) 0.6399(8) 0.7136(7) 0.034(3) Uani d 1 . .
H H13A -0.658159 0.599928 0.750468 0.041 Uiso calc 1 . .
C C14A -0.792(3) 0.7163(8) 0.7139(6) 0.034(2) Uani d 1 . .
H H14A -0.919502 0.728911 0.750532 0.041 Uiso calc 1 . .
C C16 1.538(3) -0.0082(7) 0.3870(6) 0.032(2) Uani d 1 . .
H H16 1.499738 -0.051296 0.420745 0.038 Uiso calc 1 . .
C C10A -0.210(3) 0.6517(7) 0.5523(6) 0.030(2) Uani d 1 . .
C C12A -0.447(3) 0.6194(9) 0.6618(6) 0.030(2) Uani d 1 . .
H H12A -0.338093 0.566679 0.663213 0.036 Uiso calc 1 . .
C C1A 0.078(2) 0.7089(7) 0.4525(6) 0.029(2) Uani d 1 . .
C C26 0.492(3) 0.1092(9) 0.6568(7) 0.033(3) Uani d 1 . .
H H26 0.554691 0.051109 0.665226 0.039 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'
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'
O O 0.0106 0.0060 '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
C1A N2A C21A . . 130.3(10) ?
C13 C12 C11 . . 120.4(11) ?
C1 N2 C21 . . 131.3(11) ?
C10 N1 C1 . . 128.3(9) ?
C10A N1A C1A . . 129.0(9) ?
C24A C25A C26A . . 120.0(11) ?
C22 C23 I1 . . 118.8(8) ?
C24 C23 I1 . . 120.1(8) ?
C24 C23 C22 . . 121.1(10) ?
C22 C21 N2 . . 114.4(10) ?
C26 C21 N2 . . 125.4(11) ?
C26 C21 C22 . . 120.2(11) ?
C23 C22 C21 . . 119.2(10) ?
C23A C24A C25A . . 119.1(11) ?
O1 C10 N1 . . 122.0(11) ?
O1 C10 C11 . . 121.3(11) ?
N1 C10 C11 . . 116.7(10) ?
C21A C22A C23A . . 120.6(10) ?
C21A C26A C25A . . 120.7(11) ?
N2 C1 S1 . . 127.9(9) ?
N2 C1 N1 . . 114.8(9) ?
N1 C1 S1 . . 117.2(8) ?
C16A C11A C10A . . 123.8(10) ?
C12A C11A C16A . . 120.0(11) ?
C12A C11A C10A . . 116.3(10) ?
C15 C14 C13 . . 119.7(10) ?
C24A C23A I1A . . 120.6(8) ?
C24A C23A C22A . . 120.6(10) ?
C22A C23A I1A . . 118.8(8) ?
C12 C13 C14 . . 120.3(10) ?
C12 C11 C10 . . 116.2(11) ?
C16 C11 C12 . . 118.9(11) ?
C16 C11 C10 . . 124.9(11) ?
N2A C21A C22A . . 115.1(10) ?
N2A C21A C26A . . 125.9(10) ?
C26A C21A C22A . . 119.0(11) ?
C15A C16A C11A . . 120.5(11) ?
C23 C24 C25 . . 118.4(10) ?
C14 C15 C16 . . 120.4(11) ?
C24 C25 C26 . . 121.6(10) ?
C16A C15A C14A . . 119.4(11) ?
C12A C13A C14A . . 122.3(12) ?
C13A C14A C15A . . 119.1(11) ?
C15 C16 C11 . . 120.2(11) ?
O1A C10A N1A . . 121.4(10) ?
O1A C10A C11A . . 120.8(10) ?
N1A C10A C11A . . 117.8(10) ?
C13A C12A C11A . . 118.7(12) ?
N2A C1A S1A . . 129.0(9) ?
N2A C1A N1A . . 113.2(10) ?
N1A C1A S1A . . 117.6(8) ?
C21 C26 C25 . . 119.4(12) ?
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
I1A C23A . 2.101(11) ?
I1 C23 . 2.095(11) ?
S1 C1 . 1.668(11) ?
S1A C1A . 1.658(11) ?
O1A C10A . 1.232(15) ?
O1 C10 . 1.233(15) ?
N2A C21A . 1.388(14) ?
N2A C1A . 1.345(15) ?
C12 C13 . 1.374(17) ?
C12 C11 . 1.408(16) ?
N2 C21 . 1.420(14) ?
N2 C1 . 1.335(16) ?
N1 C10 . 1.371(14) ?
N1 C1 . 1.403(14) ?
N1A C10A . 1.380(14) ?
N1A C1A . 1.414(13) ?
C25A C24A . 1.399(17) ?
C25A C26A . 1.406(18) ?
C23 C22 . 1.389(15) ?
C23 C24 . 1.385(15) ?
C21 C22 . 1.408(16) ?
C21 C26 . 1.373(17) ?
C24A C23A . 1.389(15) ?
C10 C11 . 1.501(16) ?
C22A C23A . 1.399(14) ?
C22A C21A . 1.392(15) ?
C26A C21A . 1.389(17) ?
C11A C16A . 1.397(15) ?
C11A C10A . 1.494(15) ?
C11A C12A . 1.394(16) ?
C14 C13 . 1.393(18) ?
C14 C15 . 1.382(16) ?
C11 C16 . 1.391(16) ?
C16A C15A . 1.376(15) ?
C24 C25 . 1.388(16) ?
C15 C16 . 1.390(15) ?
C25 C26 . 1.390(18) ?
C15A C14A . 1.405(17) ?
C13A C14A . 1.374(17) ?
C13A C12A . 1.374(17) ?
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
_geom_hbond_publ_flag
N2A H2A O1A . 0.88 1.85 2.602(13) 142.4 yes
N2 H2 O1 . 0.88 1.86 2.614(13) 141.9 yes
N1 H1 S1A 1_645 0.88 3.13 3.922(10) 150.4 yes
N1A H1A S1 1_465 0.88 3.12 3.884(10) 146.2 yes
