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#$Date: 2023-01-12 12:12:16 +0200 (Thu, 12 Jan 2023) $
#$Revision: 280298 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106448.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106448
loop_
_publ_author_name
'El-Hiti, Gamal A.'
'Smith, Keith'
'Alshammari, Mohammed B.'
'Hegazy, Amany S.'
'Kariuki, Benson M.'
_publ_section_title
;
 Crystal structure of 3-(4-chlorophenyl)-1,1-dimethylthiourea, C9H11ClN2S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              105
_journal_page_last               107
_journal_paper_doi               10.1515/ncrs-2016-0171
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C9 H11 Cl N2 S'
_chemical_formula_sum            'C9 H11 Cl N2 S'
_chemical_formula_weight         214.71
_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
_cell_angle_alpha                90
_cell_angle_beta                 99.733(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.8440(4)
_cell_length_b                   7.2002(2)
_cell_length_c                   10.0920(2)
_cell_measurement_reflns_used    3682
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      73.6920
_cell_measurement_theta_min      6.0300
_cell_volume                     1063.11(5)
_computing_cell_refinement       'CrysAlis PRO [20]'
_computing_data_collection       'CrysAlis PRO [20]'
_computing_data_reduction        'CrysAlis PRO [20]'
_computing_molecular_graphics    'ORTEP-3 for Windows [22]'
_computing_publication_material  'WinGX [22] and CHEMDRAW Ultra [23]'
_computing_structure_refinement  'SHELXS2013 [21]'
_computing_structure_solution    'SHELXS2013 [21]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6796
_diffrn_reflns_point_group_measured_fraction_full 0.626
_diffrn_reflns_point_group_measured_fraction_max 0.607
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.102
_diffrn_reflns_theta_min         6.049
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.655
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 423 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.09(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0399
_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)+(0.0657P)²+0.2278P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.237
_reflns_Friedel_fraction_full    0.252
_reflns_Friedel_fraction_max     0.233
_reflns_number_gt                2459
_reflns_number_total             2624
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0171_suppl.cif
_cod_data_source_block           ks1408b
_cod_original_cell_volume        1063.10(5)
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               8106448
_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   0.257
_shelx_estimated_absorpt_t_max   0.710
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3472(3) 0.5692(6) 0.5499(4) 0.0567(9) Uani 1 1 d . . . . .
C2 C 0.3470(4) 0.7518(7) 0.5039(5) 0.0683(12) Uani 1 1 d . . . . .
H2 H 0.3841 0.7853 0.4423 0.082 Uiso 1 1 calc R U . . .
C3 C 0.2915(4) 0.8835(8) 0.5499(5) 0.0796(15) Uani 1 1 d . . . . .
H3 H 0.2906 1.0051 0.5185 0.096 Uiso 1 1 calc R U . . .
C4 C 0.2380(4) 0.8326(9) 0.6421(6) 0.0788(16) Uani 1 1 d . . . . .
C5 C 0.2370(4) 0.6512(11) 0.6874(7) 0.0873(19) Uani 1 1 d . . . . .
H5 H 0.1999 0.6185 0.7494 0.105 Uiso 1 1 calc R U . . .
C6 C 0.2910(3) 0.5191(8) 0.6403(5) 0.0700(12) Uani 1 1 d . . . . .
H6 H 0.2896 0.3966 0.6692 0.084 Uiso 1 1 calc R U . . .
C7 C 0.4626(3) 0.3173(5) 0.5665(4) 0.0470(8) Uani 1 1 d . . . . .
C8 C 0.4746(5) 0.1813(6) 0.3474(5) 0.0721(14) Uani 1 1 d . . . . .
H8A H 0.4092 0.1721 0.3253 0.108 Uiso 1 1 calc R U . . .
H8B H 0.5018 0.0723 0.3164 0.108 Uiso 1 1 calc R U . . .
H8C H 0.4948 0.2891 0.3047 0.108 Uiso 1 1 calc R U . . .
C9 C 0.5743(4) 0.0710(7) 0.5525(5) 0.0688(12) Uani 1 1 d . . . . .
H9A H 0.5915 0.0984 0.6465 0.103 Uiso 1 1 calc R U . . .
H9B H 0.6263 0.0863 0.5084 0.103 Uiso 1 1 calc R U . . .
H9C H 0.5528 -0.0548 0.5417 0.103 Uiso 1 1 calc R U . . .
C10 C 0.8885(3) 0.9278(6) 0.1826(4) 0.0539(9) Uani 1 1 d . . . . .
C11 C 0.9454(3) 0.9755(6) 0.3009(5) 0.0595(10) Uani 1 1 d . . . . .
H11 H 0.9479 1.0977 0.3310 0.071 Uiso 1 1 calc R U . . .
C12 C 0.9989(3) 0.8400(7) 0.3744(6) 0.0680(12) Uani 1 1 d . . . . .
H12 H 1.0369 0.8707 0.4544 0.082 Uiso 1 1 calc R U . . .
C13 C 0.9950(3) 0.6572(7) 0.3270(5) 0.0619(11) Uani 1 1 d . . . . .
C14 C 0.9412(4) 0.6117(7) 0.2098(5) 0.0685(12) Uani 1 1 d . . . . .
H14 H 0.9405 0.4905 0.1778 0.082 Uiso 1 1 calc R U . . .
C15 C 0.8872(4) 0.7461(6) 0.1374(4) 0.0628(10) Uani 1 1 d . . . . .
H15 H 0.8495 0.7140 0.0574 0.075 Uiso 1 1 calc R U . . .
C16 C 0.7738(3) 1.1821(4) 0.1435(4) 0.0451(8) Uani 1 1 d . . . . .
C17 C 0.6630(4) 1.4272(7) 0.0756(5) 0.0661(11) Uani 1 1 d . . . . .
H17A H 0.6418 1.3906 0.1565 0.099 Uiso 1 1 calc R U . . .
H17B H 0.6133 1.4214 0.0013 0.099 Uiso 1 1 calc R U . . .
H17C H 0.6860 1.5520 0.0853 0.099 Uiso 1 1 calc R U . . .
C18 C 0.7619(4) 1.3199(6) -0.0812(5) 0.0686(13) Uani 1 1 d . . . . .
H18A H 0.8272 1.3293 -0.0714 0.103 Uiso 1 1 calc R U . . .
H18B H 0.7344 1.4293 -0.1250 0.103 Uiso 1 1 calc R U . . .
H18C H 0.7414 1.2126 -0.1343 0.103 Uiso 1 1 calc R U . . .
N1 N 0.4026(3) 0.4389(5) 0.4958(3) 0.0609(9) Uani 1 1 d . . . . .
H1 H 0.3979 0.4363 0.4097 0.073 Uiso 1 1 calc R U . . .
N2 N 0.5016(3) 0.1974(4) 0.4929(4) 0.0531(8) Uani 1 1 d . . . . .
N3 N 0.8341(3) 1.0604(5) 0.1022(3) 0.0583(8) Uani 1 1 d . . . . .
H3A H 0.8395 1.0649 0.0187 0.070 Uiso 1 1 calc R U . . .
N4 N 0.7356(3) 1.3025(4) 0.0511(3) 0.0514(7) Uani 1 1 d . . . . .
S1 S 0.48905(8) 0.32265(14) 0.73619(9) 0.0591(3) Uani 1 1 d . . . . .
S2 S 0.74814(8) 1.17450(14) 0.30027(9) 0.0570(3) Uani 1 1 d . . . . .
Cl1 Cl 0.16859(13) 0.9989(3) 0.6997(2) 0.1229(8) Uani 1 1 d . . . . .
Cl2 Cl 1.06072(11) 0.4871(2) 0.42090(16) 0.0923(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 119.8(4) . .
C6 C1 N1 122.4(4) . .
C2 C1 N1 117.7(4) . .
C3 C2 C1 120.1(5) . .
C3 C2 H2 119.9 . .
C1 C2 H2 119.9 . .
C4 C3 C2 119.3(6) . .
C4 C3 H3 120.4 . .
C2 C3 H3 120.4 . .
C3 C4 C5 121.1(5) . .
C3 C4 Cl1 119.0(5) . .
C5 C4 Cl1 119.9(5) . .
C6 C5 C4 119.8(6) . .
C6 C5 H5 120.1 . .
C4 C5 H5 120.1 . .
C5 C6 C1 119.9(5) . .
C5 C6 H6 120.1 . .
C1 C6 H6 120.1 . .
N2 C7 N1 115.6(3) . .
N2 C7 S1 122.0(3) . .
N1 C7 S1 122.3(3) . .
N2 C8 H8A 109.5 . .
N2 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N2 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N2 C9 H9A 109.5 . .
N2 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N2 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C15 C10 C11 119.5(4) . .
C15 C10 N3 118.3(4) . .
C11 C10 N3 122.2(4) . .
C10 C11 C12 119.7(4) . .
C10 C11 H11 120.1 . .
C12 C11 H11 120.1 . .
C11 C12 C13 119.4(5) . .
C11 C12 H12 120.3 . .
C13 C12 H12 120.3 . .
C14 C13 C12 120.8(4) . .
C14 C13 Cl2 120.0(4) . .
C12 C13 Cl2 119.3(4) . .
C13 C14 C15 119.8(5) . .
C13 C14 H14 120.1 . .
C15 C14 H14 120.1 . .
C14 C15 C10 120.8(4) . .
C14 C15 H15 119.6 . .
C10 C15 H15 119.6 . .
N4 C16 N3 115.3(3) . .
N4 C16 S2 122.8(3) . .
N3 C16 S2 121.9(3) . .
N4 C17 H17A 109.5 . .
N4 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
N4 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N4 C18 H18A 109.5 . .
N4 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N4 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C7 N1 C1 126.5(3) . .
C7 N1 H1 116.7 . .
C1 N1 H1 116.7 . .
C7 N2 C9 122.3(4) . .
C7 N2 C8 122.7(4) . .
C9 N2 C8 115.0(4) . .
C16 N3 C10 126.7(3) . .
C16 N3 H3A 116.7 . .
C10 N3 H3A 116.7 . .
C16 N4 C17 121.6(4) . .
C16 N4 C18 123.4(3) . .
C17 N4 C18 115.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.384(7) .
C1 C2 1.394(7) .
C1 N1 1.417(5) .
C2 C3 1.386(7) .
C2 H2 0.9300 .
C3 C4 1.372(9) .
C3 H3 0.9300 .
C4 C5 1.385(9) .
C4 Cl1 1.742(5) .
C5 C6 1.379(8) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 N2 1.333(5) .
C7 N1 1.362(5) .
C7 S1 1.692(4) .
C8 N2 1.460(6) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 N2 1.461(6) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 C15 1.384(6) .
C10 C11 1.384(7) .
C10 N3 1.415(5) .
C11 C12 1.390(7) .
C11 H11 0.9300 .
C12 C13 1.398(7) .
C12 H12 0.9300 .
C13 C14 1.351(7) .
C13 Cl2 1.743(4) .
C14 C15 1.384(6) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 N4 1.328(5) .
C16 N3 1.367(5) .
C16 S2 1.690(4) .
C17 N4 1.456(6) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 N4 1.459(5) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
N1 H1 0.8600 .
N3 H3A 0.8600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 S1 0.86 2.95 3.549(4) 128.3 2_564
N3 H3A S2 0.86 2.94 3.530(4) 127.1 2_574
