#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/96/2209627.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_2209627
loop_
_publ_author_name
'Saeed, Aamer'
'Flörke, Ulrich'
_publ_section_title
;
 1-(4-Chlorophenyl)-3-(4-methylbenzoyl)thiourea
;
_journal_coeditor_code           OM2022
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2924
_journal_page_last               o2925
_journal_paper_doi               10.1107/S1600536806022501
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C15 H13 Cl N2 O S'
_chemical_formula_moiety         'C15 H13 Cl N2 O S'
_chemical_formula_sum            'C15 H13 Cl N2 O S'
_chemical_formula_weight         304.78
_chemical_name_systematic
;
1-(4-Chlorophenyl)-3-(4-methylbenzoyl)thiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.3370(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0097(8)
_cell_length_b                   6.3118(4)
_cell_length_c                   18.8101(13)
_cell_measurement_reflns_used    3569
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.20
_cell_volume                     1402.72(16)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2002)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX-I'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13563
_diffrn_reflns_theta_full        28.08
_diffrn_reflns_theta_max         28.08
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.417
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_correction_T_min  0.8249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.5904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1093
_reflns_number_gt                2905
_reflns_number_total             3401
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2022.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209627
_cod_database_fobs_code          2209627
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_refinement_flags
_atom_site_occupancy
Cl Cl1 0.48119(5) 0.01325(7) 0.19470(3) 0.03474(15) Uani d . 1
S S1 0.09352(4) 0.85729(8) 0.08769(2) 0.02765(14) Uani d . 1
O O1 0.34926(11) 1.0711(2) -0.04939(7) 0.0289(3) Uani d . 1
N N1 0.29415(12) 0.7946(2) 0.04500(7) 0.0203(3) Uani d . 1
H H1A 0.3420 0.8504 0.0199 0.024 Uiso calc R 1
N N2 0.18287(13) 1.0696(2) -0.00688(8) 0.0210(3) Uani d . 1
H H2B 0.1172 1.1347 -0.0115 0.025 Uiso calc R 1
C C1 0.33294(15) 0.6059(3) 0.08288(9) 0.0192(3) Uani d . 1
C C2 0.26801(16) 0.4793(3) 0.11994(10) 0.0259(4) Uani d . 1
H H2A 0.1923 0.5181 0.1221 0.031 Uiso calc R 1
C C3 0.31430(17) 0.2959(3) 0.15380(10) 0.0274(4) Uani d . 1
H H3A 0.2707 0.2100 0.1800 0.033 Uiso calc R 1
C C4 0.42318(16) 0.2387(3) 0.14937(9) 0.0230(4) Uani d . 1
C C5 0.48776(16) 0.3606(3) 0.11171(10) 0.0269(4) Uani d . 1
H H5A 0.5625 0.3182 0.1082 0.032 Uiso calc R 1
C C6 0.44256(15) 0.5460(3) 0.07896(10) 0.0243(4) Uani d . 1
H H6A 0.4871 0.6325 0.0537 0.029 Uiso calc R 1
C C7 0.19736(14) 0.9009(3) 0.04119(9) 0.0198(3) Uani d . 1
C C8 0.25655(15) 1.1501(3) -0.04845(9) 0.0208(3) Uani d . 1
C C9 0.21392(14) 1.3399(3) -0.09208(9) 0.0191(3) Uani d . 1
C C10 0.13269(15) 1.4750(3) -0.07303(9) 0.0214(4) Uani d . 1
H H10A 0.1024 1.4475 -0.0307 0.026 Uiso calc R 1
C C11 0.09570(15) 1.6494(3) -0.11535(9) 0.0221(4) Uani d . 1
H H11A 0.0395 1.7394 -0.1020 0.027 Uiso calc R 1
C C12 0.13973(15) 1.6949(3) -0.17722(9) 0.0219(4) Uani d . 1
C C13 0.22205(16) 1.5610(3) -0.19544(9) 0.0254(4) Uani d . 1
H H13A 0.2536 1.5906 -0.2372 0.031 Uiso calc R 1
C C14 0.25896(15) 1.3849(3) -0.15374(9) 0.0234(4) Uani d . 1
H H14A 0.3150 1.2947 -0.1672 0.028 Uiso calc R 1
C C15 0.09912(19) 1.8846(3) -0.22293(10) 0.0313(4) Uani d . 1
H H15A 0.0494 1.9703 -0.1985 0.047 Uiso calc R 1
H H15B 0.0573 1.8373 -0.2698 0.047 Uiso calc R 1
H H15C 0.1643 1.9699 -0.2303 0.047 Uiso calc R 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'
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C7 N1 C1 130.71(15) y
C7 N1 H1A 114.6 ?
C1 N1 H1A 114.6 ?
C8 N2 C7 129.34(15) y
C8 N2 H2B 115.3 ?
C7 N2 H2B 115.3 ?
C6 C1 C2 119.65(16) ?
C6 C1 N1 115.53(15) ?
C2 C1 N1 124.78(16) ?
C1 C2 C3 119.70(17) ?
C1 C2 H2A 120.1 ?
C3 C2 H2A 120.1 ?
C4 C3 C2 119.89(17) ?
C4 C3 H3A 120.1 ?
C2 C3 H3A 120.1 ?
C3 C4 C5 121.03(16) ?
C3 C4 Cl1 119.15(14) ?
C5 C4 Cl1 119.79(14) ?
C4 C5 C6 119.25(17) ?
C4 C5 H5A 120.4 ?
C6 C5 H5A 120.4 ?
C1 C6 C5 120.46(17) ?
C1 C6 H6A 119.8 ?
C5 C6 H6A 119.8 ?
N1 C7 N2 115.31(15) ?
N1 C7 S1 127.95(13) ?
N2 C7 S1 116.73(12) ?
O1 C8 N2 122.47(16) ?
O1 C8 C9 122.92(15) ?
N2 C8 C9 114.61(15) ?
C10 C9 C14 118.98(15) ?
C10 C9 C8 122.61(15) ?
C14 C9 C8 118.40(15) ?
C11 C10 C9 120.48(16) ?
C11 C10 H10A 119.8 ?
C9 C10 H10A 119.8 ?
C10 C11 C12 120.92(16) ?
C10 C11 H11A 119.5 ?
C12 C11 H11A 119.5 ?
C13 C12 C11 118.35(16) ?
C13 C12 C15 121.03(16) ?
C11 C12 C15 120.62(16) ?
C14 C13 C12 121.16(16) ?
C14 C13 H13A 119.4 ?
C12 C13 H13A 119.4 ?
C13 C14 C9 120.10(16) ?
C13 C14 H14A 120.0 ?
C9 C14 H14A 120.0 ?
C12 C15 H15A 109.5 ?
C12 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C12 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.7393(17) y
S1 C7 1.6696(18) y
O1 C8 1.223(2) y
N1 C7 1.333(2) y
N1 C1 1.422(2) y
N1 H1A 0.8800 ?
N2 C8 1.379(2) y
N2 C7 1.388(2) y
N2 H2B 0.8800 ?
C1 C6 1.384(2) ?
C1 C2 1.388(2) ?
C2 C3 1.389(2) ?
C2 H2A 0.9500 ?
C3 C4 1.373(3) ?
C3 H3A 0.9500 ?
C4 C5 1.376(3) ?
C5 C6 1.387(2) ?
C5 H5A 0.9500 ?
C6 H6A 0.9500 ?
C8 C9 1.490(2) ?
C9 C10 1.390(2) ?
C9 C14 1.394(2) ?
C10 C11 1.384(2) ?
C10 H10A 0.9500 ?
C11 C12 1.392(2) ?
C11 H11A 0.9500 ?
C12 C13 1.389(3) ?
C12 C15 1.504(2) ?
C13 C14 1.386(2) ?
C13 H13A 0.9500 ?
C14 H14A 0.9500 ?
C15 H15A 0.9800 ?
C15 H15B 0.9800 ?
C15 H15C 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
N1 H1A O1 . 0.88 1.92 2.6567(19) 140.2
N2 H2B S1 3_575 0.88 2.68 3.4250(15) 143.8
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
_geom_torsion_publ_flag
C7 N1 C1 C6 -175.68(17) ?
C7 N1 C1 C2 6.7(3) ?
C6 C1 C2 C3 1.1(3) ?
N1 C1 C2 C3 178.67(16) ?
C1 C2 C3 C4 -1.2(3) ?
C2 C3 C4 C5 0.0(3) ?
C2 C3 C4 Cl1 177.84(14) ?
C3 C4 C5 C6 1.2(3) ?
Cl1 C4 C5 C6 -176.63(14) ?
C2 C1 C6 C5 0.1(3) ?
N1 C1 C6 C5 -177.69(15) ?
C4 C5 C6 C1 -1.2(3) ?
C1 N1 C7 N2 -174.03(15) ?
C1 N1 C7 S1 6.8(3) ?
C8 N2 C7 N1 -3.8(3) y
C8 N2 C7 S1 175.44(14) ?
C7 N2 C8 O1 2.5(3) y
C7 N2 C8 C9 -177.62(16) ?
O1 C8 C9 C10 -155.54(18) ?
N2 C8 C9 C10 24.6(2) y
O1 C8 C9 C14 23.4(3) ?
N2 C8 C9 C14 -156.45(16) ?
C14 C9 C10 C11 1.1(3) ?
C8 C9 C10 C11 -179.96(15) ?
C9 C10 C11 C12 -0.8(3) ?
C10 C11 C12 C13 -0.1(3) ?
C10 C11 C12 C15 179.99(16) ?
C11 C12 C13 C14 0.7(3) ?
C15 C12 C13 C14 -179.43(17) ?
C12 C13 C14 C9 -0.3(3) ?
C10 C9 C14 C13 -0.6(3) ?
C8 C9 C14 C13 -179.53(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 794531
