#------------------------------------------------------------------------------
#$Date: 2021-02-05 16:53:19 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261799 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022286.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_2022286
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-o-iodophenylthiourea
_chemical_name_systematic
;
1-Benzoyl-3-(2-iodophenyl)thiourea
;
_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   geom
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                84.408(9)
_cell_angle_beta                 89.142(9)
_cell_angle_gamma                65.933(8)
_cell_formula_units_Z            2
_cell_length_a                   6.2410(7)
_cell_length_b                   7.2420(8)
_cell_length_c                   16.709(2)
_cell_measurement_reflns_used    15454
_cell_measurement_temperature    125
_cell_measurement_theta_max      58.91
_cell_measurement_theta_min      5.00
_cell_volume                     686.02(14)
_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      125.0
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7847
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.976
_diffrn_reflns_theta_min         2.450
_exptl_absorpt_coefficient_mu    2.479
_exptl_absorpt_correction_T_max  0.6438
_exptl_absorpt_correction_T_min  0.4049
_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    1.850
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.384
_exptl_crystal_size_mid          0.363
_exptl_crystal_size_min          0.199
_refine_diff_density_max         0.703
_refine_diff_density_min         -0.937
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0276
_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/[σ²(Fo²)+(0.0390P)²+0.7088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                3508
_reflns_number_total             3616
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wp3011sup1.cif
_cod_data_source_block           7
_cod_depositor_comments
'Adding full bibliography for 2022286--2022290.cif.'
_cod_database_code               2022286
_cod_database_fobs_code          2022286
_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   0.450
_shelx_estimated_absorpt_t_max   0.638
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 0.90242(2) 0.02230(2) 0.15049(2) 0.03196(7) Uani d 1 . .
S S1 0.15430(10) 0.46926(10) 0.22234(3) 0.03037(13) Uani d 1 . .
O O1 0.7747(3) 0.2798(3) 0.39791(9) 0.0285(3) Uani d 1 . .
N N2 0.6016(3) 0.4070(3) 0.24851(10) 0.0211(3) Uani d 1 . .
H H2 0.723735 0.364016 0.281876 0.025 Uiso calc 1 . .
N N1 0.3991(3) 0.3503(3) 0.35827(10) 0.0220(3) Uani d 1 . .
H H1 0.265397 0.351322 0.376215 0.026 Uiso calc 1 . .
C C26 0.7606(3) 0.3342(3) 0.11447(12) 0.0228(4) Uani d 1 . .
C C22 0.5295(4) 0.6780(4) 0.14173(13) 0.0261(4) Uani d 1 . .
H H22 0.440446 0.772704 0.177811 0.031 Uiso calc 1 . .
C C11 0.5187(4) 0.2440(3) 0.49911(11) 0.0210(4) Uani d 1 . .
C C21 0.6289(3) 0.4723(3) 0.16703(11) 0.0207(4) Uani d 1 . .
C C1 0.4010(3) 0.4079(3) 0.27636(12) 0.0208(3) Uani d 1 . .
C C10 0.5784(4) 0.2919(3) 0.41490(12) 0.0210(3) Uani d 1 . .
C C12 0.7032(4) 0.1607(4) 0.55539(13) 0.0282(4) Uani d 1 . .
H H12 0.858015 0.137499 0.539275 0.034 Uiso calc 1 . .
C C25 0.7944(4) 0.4025(4) 0.03653(13) 0.0298(5) Uani d 1 . .
H H25 0.886598 0.308343 0.000756 0.036 Uiso calc 1 . .
C C23 0.5600(4) 0.7459(4) 0.06345(14) 0.0326(5) Uani d 1 . .
H H23 0.489514 0.886869 0.045740 0.039 Uiso calc 1 . .
C C16 0.2916(4) 0.2777(3) 0.52341(13) 0.0261(4) Uani d 1 . .
H H16 0.164269 0.333137 0.485342 0.031 Uiso calc 1 . .
C C24 0.6928(4) 0.6084(5) 0.01139(14) 0.0342(5) Uani d 1 . .
H H24 0.714536 0.655435 -0.041909 0.041 Uiso calc 1 . .
C C13 0.6637(5) 0.1113(4) 0.63477(14) 0.0340(5) Uani d 1 . .
H H13 0.791269 0.052973 0.672691 0.041 Uiso calc 1 . .
C C14 0.4383(5) 0.1469(4) 0.65881(13) 0.0309(5) Uani d 1 . .
H H14 0.410940 0.114186 0.713373 0.037 Uiso calc 1 . .
C C15 0.2522(4) 0.2301(4) 0.60339(14) 0.0301(4) Uani d 1 . .
H H15 0.097554 0.254730 0.620068 0.036 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
C21 N2 H2 . . 118.4 ?
C1 N2 H2 . . 118.4 ?
C1 N2 C21 . . 123.21(17) ?
C1 N1 H1 . . 115.7 ?
C10 N1 H1 . . 115.7 ?
C10 N1 C1 . . 128.69(17) ?
C21 C26 I1 . . 120.46(15) ?
C21 C26 C25 . . 120.1(2) ?
C25 C26 I1 . . 119.44(17) ?
C21 C22 H22 . . 120.0 ?
C21 C22 C23 . . 119.9(2) ?
C23 C22 H22 . . 120.0 ?
C12 C11 C10 . . 116.82(19) ?
C12 C11 C16 . . 119.26(19) ?
C16 C11 C10 . . 123.92(18) ?
C26 C21 N2 . . 121.15(19) ?
C22 C21 N2 . . 118.82(19) ?
C22 C21 C26 . . 119.98(19) ?
N2 C1 S1 . . 126.10(15) ?
N2 C1 N1 . . 116.28(17) ?
N1 C1 S1 . . 117.62(15) ?
O1 C10 N1 . . 122.48(18) ?
O1 C10 C11 . . 121.69(18) ?
N1 C10 C11 . . 115.83(18) ?
C11 C12 H12 . . 119.7 ?
C13 C12 C11 . . 120.6(2) ?
C13 C12 H12 . . 119.7 ?
C26 C25 H25 . . 120.2 ?
C24 C25 C26 . . 119.6(2) ?
C24 C25 H25 . . 120.2 ?
C22 C23 H23 . . 120.0 ?
C24 C23 C22 . . 120.0(2) ?
C24 C23 H23 . . 120.0 ?
C11 C16 H16 . . 120.0 ?
C15 C16 C11 . . 119.9(2) ?
C15 C16 H16 . . 120.0 ?
C25 C24 H24 . . 119.8 ?
C23 C24 C25 . . 120.3(2) ?
C23 C24 H24 . . 119.8 ?
C12 C13 H13 . . 120.0 ?
C14 C13 C12 . . 120.0(2) ?
C14 C13 H13 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C13 C14 C15 . . 120.1(2) ?
C15 C14 H14 . . 120.0 ?
C16 C15 H15 . . 119.9 ?
C14 C15 C16 . . 120.1(2) ?
C14 C15 H15 . . 119.9 ?
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 C26 . 2.090(2) ?
S1 C1 . 1.670(2) ?
O1 C10 . 1.224(3) ?
N2 H2 . 0.8800 ?
N2 C21 . 1.428(2) ?
N2 C1 . 1.326(3) ?
N1 H1 . 0.8800 ?
N1 C1 . 1.393(2) ?
N1 C10 . 1.376(3) ?
C26 C21 . 1.388(3) ?
C26 C25 . 1.392(3) ?
C22 H22 . 0.9500 ?
C22 C21 . 1.384(3) ?
C22 C23 . 1.390(3) ?
C11 C10 . 1.494(3) ?
C11 C12 . 1.389(3) ?
C11 C16 . 1.397(3) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.385(3) ?
C25 H25 . 0.9500 ?
C25 C24 . 1.385(4) ?
C23 H23 . 0.9500 ?
C23 C24 . 1.381(4) ?
C16 H16 . 0.9500 ?
C16 C15 . 1.391(3) ?
C24 H24 . 0.9500 ?
C13 H13 . 0.9500 ?
C13 C14 . 1.384(4) ?
C14 H14 . 0.9500 ?
C14 C15 . 1.386(3) ?
C15 H15 . 0.9500 ?
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
N2 H2 O1 . 0.88 1.97 2.659(2) 134.7 yes
