#------------------------------------------------------------------------------
#$Date: 2021-02-05 16:53:19 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261799 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022288.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_2022288
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-p-iodophenylthiourea
_chemical_name_systematic
;
1-Benzoyl-3-(4-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                61.622(7)
_cell_angle_beta                 86.203(9)
_cell_angle_gamma                85.241(9)
_cell_formula_units_Z            2
_cell_length_a                   4.4279(5)
_cell_length_b                   13.0767(14)
_cell_length_c                   13.4410(14)
_cell_measurement_reflns_used    17633
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      3.00
_cell_volume                     682.06(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      120.0
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9681
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         3.001
_exptl_absorpt_coefficient_mu    2.493
_exptl_absorpt_correction_T_max  0.9317
_exptl_absorpt_correction_T_min  0.7340
_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    1.861
_exptl_crystal_description       needle
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.800
_refine_diff_density_min         -0.392
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0209
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0365P)²+0.1682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0542
_reflns_number_gt                3348
_reflns_number_total             3617
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wp3011sup1.cif
_cod_data_source_block           9
_cod_depositor_comments
'Adding full bibliography for 2022286--2022290.cif.'
_cod_original_cell_volume        682.06(13)
_cod_database_code               2022288
_cod_database_fobs_code          2022288
_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   0.490
_shelx_estimated_absorpt_t_max   0.892
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 1.54166(3) 0.97722(2) 0.30315(2) 0.02325(5) Uani d 1 . .
S S1 0.69441(13) 0.63634(4) 0.85377(4) 0.02636(10) Uani d 1 . .
O O1 0.4225(3) 0.43021(12) 0.68414(11) 0.0242(3) Uani d 1 . .
N N2 0.7238(4) 0.60053(13) 0.67111(13) 0.0195(3) Uani d 1 . .
H H2 0.659541 0.556723 0.644375 0.023 Uiso calc 1 . .
N N1 0.4100(4) 0.48760(13) 0.82067(13) 0.0198(3) Uani d 1 . .
H H1 0.322999 0.474879 0.886008 0.024 Uiso calc 1 . .
C C24 1.2997(4) 0.84543(15) 0.43373(15) 0.0191(3) Uani d 1 . .
C C21 0.9269(4) 0.68403(15) 0.59760(14) 0.0176(3) Uani d 1 . .
C C23 1.1904(4) 0.86015(16) 0.52524(16) 0.0221(3) Uani d 1 . .
H H23 1.243847 0.925496 0.531840 0.026 Uiso calc 1 . .
C C22 1.0024(4) 0.77975(16) 0.60781(16) 0.0220(3) Uani d 1 . .
H H22 0.926668 0.790207 0.670373 0.026 Uiso calc 1 . .
C C11 0.1253(4) 0.32291(15) 0.85074(14) 0.0178(3) Uani d 1 . .
C C12 0.0857(4) 0.23904(16) 0.81704(16) 0.0214(3) Uani d 1 . .
H H12 0.183570 0.245258 0.749489 0.026 Uiso calc 1 . .
C C1 0.6126(4) 0.57668(15) 0.77422(15) 0.0195(3) Uani d 1 . .
C C25 1.2329(4) 0.74801(16) 0.42476(15) 0.0212(3) Uani d 1 . .
H H25 1.314542 0.736362 0.363510 0.025 Uiso calc 1 . .
C C26 1.0454(4) 0.66836(16) 0.50665(15) 0.0209(3) Uani d 1 . .
H H26 0.996650 0.602062 0.500796 0.025 Uiso calc 1 . .
C C10 0.3288(4) 0.41730(15) 0.77783(15) 0.0182(3) Uani d 1 . .
C C14 -0.2385(5) 0.13765(17) 0.98032(16) 0.0239(4) Uani d 1 . .
H H14 -0.361951 0.074328 1.024676 0.029 Uiso calc 1 . .
C C16 -0.0220(4) 0.31351(16) 0.94942(15) 0.0216(3) Uani d 1 . .
H H16 0.000485 0.370853 0.972299 0.026 Uiso calc 1 . .
C C15 -0.2017(5) 0.22064(17) 1.01444(16) 0.0241(4) Uani d 1 . .
H H15 -0.299221 0.213934 1.082217 0.029 Uiso calc 1 . .
C C13 -0.0951(5) 0.14698(17) 0.88137(17) 0.0246(4) Uani d 1 . .
H H13 -0.121186 0.090296 0.857955 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'
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0390
0 -1 -1 0.0210
0 1 0 0.0430
0 -14 1 0.0360
17 6 -2 0.1330
-28 -10 -9 0.2560
0 6 29 0.0440
0 -7 -33 0.0460
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 . . 114.5 ?
C1 N2 H2 . . 114.5 ?
C1 N2 C21 . . 131.06(16) ?
C1 N1 H1 . . 115.7 ?
C10 N1 H1 . . 115.7 ?
C10 N1 C1 . . 128.66(15) ?
C23 C24 I1 . . 119.07(13) ?
C23 C24 C25 . . 120.57(17) ?
C25 C24 I1 . . 120.23(13) ?
C22 C21 N2 . . 124.91(16) ?
C22 C21 C26 . . 119.73(17) ?
C26 C21 N2 . . 115.30(15) ?
C24 C23 H23 . . 119.8 ?
C24 C23 C22 . . 120.46(17) ?
C22 C23 H23 . . 119.8 ?
C21 C22 C23 . . 119.28(17) ?
C21 C22 H22 . . 120.4 ?
C23 C22 H22 . . 120.4 ?
C12 C11 C10 . . 116.82(16) ?
C16 C11 C12 . . 119.22(17) ?
C16 C11 C10 . . 123.95(16) ?
C11 C12 H12 . . 119.8 ?
C13 C12 C11 . . 120.50(17) ?
C13 C12 H12 . . 119.8 ?
N2 C1 S1 . . 128.09(15) ?
N2 C1 N1 . . 114.60(16) ?
N1 C1 S1 . . 117.28(13) ?
C24 C25 H25 . . 120.6 ?
C26 C25 C24 . . 118.89(16) ?
C26 C25 H25 . . 120.6 ?
C21 C26 H26 . . 119.5 ?
C25 C26 C21 . . 121.00(16) ?
C25 C26 H26 . . 119.5 ?
O1 C10 N1 . . 122.06(17) ?
O1 C10 C11 . . 121.19(16) ?
N1 C10 C11 . . 116.74(15) ?
C15 C14 H14 . . 119.9 ?
C15 C14 C13 . . 120.15(18) ?
C13 C14 H14 . . 119.9 ?
C11 C16 H16 . . 119.9 ?
C15 C16 C11 . . 120.28(17) ?
C15 C16 H16 . . 119.9 ?
C14 C15 C16 . . 119.97(17) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C12 C13 C14 . . 119.86(18) ?
C12 C13 H13 . . 120.1 ?
C14 C13 H13 . . 120.1 ?
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 C24 . 2.0930(18) ?
S1 C1 . 1.6656(19) ?
O1 C10 . 1.236(2) ?
N2 H2 . 0.8800 ?
N2 C21 . 1.413(2) ?
N2 C1 . 1.336(2) ?
N1 H1 . 0.8800 ?
N1 C1 . 1.400(2) ?
N1 C10 . 1.375(2) ?
C24 C23 . 1.384(2) ?
C24 C25 . 1.392(3) ?
C21 C22 . 1.392(2) ?
C21 C26 . 1.395(2) ?
C23 H23 . 0.9500 ?
C23 C22 . 1.394(3) ?
C22 H22 . 0.9500 ?
C11 C12 . 1.398(2) ?
C11 C10 . 1.488(2) ?
C11 C16 . 1.394(2) ?
C12 H12 . 0.9500 ?
C12 C13 . 1.384(3) ?
C25 H25 . 0.9500 ?
C25 C26 . 1.385(3) ?
C26 H26 . 0.9500 ?
C14 H14 . 0.9500 ?
C14 C15 . 1.388(3) ?
C14 C13 . 1.391(3) ?
C16 H16 . 0.9500 ?
C16 C15 . 1.389(3) ?
C15 H15 . 0.9500 ?
C13 H13 . 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 1.87 2.620(2) 141.9 yes
N1 H1 S1 2_667 0.88 3.08 3.8864(17) 152.8 yes
C22 H22 S1 . 0.95 2.54 3.200(2) 126.3 yes
