#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/71/2237198.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_2237198
loop_
_publ_author_name
'Rauf, M. Khawar'
'Ebihara, Masahiro'
'Badshah, Amin'
_publ_section_title
;
 1-(2-Chlorobenzoyl)-3-(3-methoxyphenyl)thiourea
;
_journal_coeditor_code           MW2100
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o19
_journal_paper_doi               10.1107/S1600536812048830
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C15 H13 Cl N2 O2 S'
_chemical_formula_moiety         'C15 H13 Cl N2 O2 S'
_chemical_formula_sum            'C15 H13 Cl N2 O2 S'
_chemical_formula_weight         320.78
_chemical_name_common            1-(2-Chlorobenzoyl)-3-(3-methoxyphenyl)thiourea
_chemical_name_systematic
;
1-(2-Chlorobenzoyl)-3-(3-methoxyphenyl)thiourea
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.541(7)
_cell_angle_beta                 93.305(6)
_cell_angle_gamma                96.918(7)
_cell_formula_units_Z            2
_cell_length_a                   6.276(3)
_cell_length_b                   10.202(5)
_cell_length_c                   11.411(5)
_cell_measurement_reflns_used    2546
_cell_measurement_temperature    123.1500
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.2751
_cell_volume                     721.4(6)
_computing_cell_refinement
'CrystalClear (Molecular Structure Corporation & Rigaku, 2001)'
_computing_data_collection
'CrystalClear (Molecular Structure Corporation & Rigaku, 2001)'
_computing_data_reduction
'CrystalClear (Molecular Structure Corporation & Rigaku, 2001)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material
'Yadokari-XG (Wakita, 2001; Kabuto et al., 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 14.62
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5698
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.336
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3222
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0309P)²+0.5054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0877
_reflns_number_gt                3071
_reflns_number_total             3222
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            mw2100.cif
_cod_data_source_block           I
_cod_original_cell_volume        721.3(6)
_cod_database_code               2237198
_cod_database_fobs_code          2237198
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.6542(2) 0.57142(13) 0.79707(12) 0.0144(3) Uani d . 1 1
O O1 0.58303(17) 0.56062(10) 0.89370(9) 0.0186(2) Uani d . 1 1
N N1 0.56572(19) 0.49567(12) 0.69582(11) 0.0155(2) Uani d . 1 1
H H1 0.6364 0.5052 0.6320 0.019 Uiso calc R 1 1
C C2 0.3774(2) 0.40595(13) 0.68314(13) 0.0147(3) Uani d . 1 1
S S1 0.28505(7) 0.34880(4) 0.54559(3) 0.02392(12) Uani d . 1 1
N N2 0.28727(18) 0.37856(12) 0.78283(10) 0.0148(2) Uani d . 1 1
H H2 0.3660 0.4085 0.8479 0.018 Uiso calc R 1 1
C C3 0.8470(2) 0.66726(14) 0.77733(12) 0.0149(3) Uani d . 1 1
C C4 0.8823(2) 0.79519(14) 0.83489(13) 0.0168(3) Uani d . 1 1
C C5 1.0642(3) 0.88129(15) 0.81696(14) 0.0217(3) Uani d . 1 1
H H5 1.0863 0.9678 0.8566 0.026 Uiso calc R 1 1
C C6 1.2135(2) 0.84109(16) 0.74122(15) 0.0236(3) Uani d . 1 1
H H6 1.3379 0.9001 0.7292 0.028 Uiso calc R 1 1
C C7 1.1816(2) 0.71488(16) 0.68298(14) 0.0219(3) Uani d . 1 1
H H7 1.2837 0.6875 0.6309 0.026 Uiso calc R 1 1
C C8 0.9996(2) 0.62846(15) 0.70116(13) 0.0179(3) Uani d . 1 1
H H8 0.9787 0.5420 0.6614 0.021 Uiso calc R 1 1
Cl Cl1 0.69817(6) 0.85411(4) 0.92737(3) 0.02243(11) Uani d . 1 1
C C9 0.0829(2) 0.30814(13) 0.79995(12) 0.0141(3) Uani d . 1 1
C C10 -0.0238(2) 0.20764(14) 0.72013(13) 0.0166(3) Uani d . 1 1
H H10 0.0399 0.1801 0.6503 0.020 Uiso calc R 1 1
C C11 -0.2262(2) 0.14852(14) 0.74534(13) 0.0164(3) Uani d . 1 1
C C12 -0.3209(2) 0.18776(14) 0.84774(13) 0.0181(3) Uani d . 1 1
H H12 -0.4605 0.1482 0.8627 0.022 Uiso calc R 1 1
C C13 -0.2092(2) 0.28502(15) 0.92748(13) 0.0186(3) Uani d . 1 1
H H13 -0.2712 0.3107 0.9984 0.022 Uiso calc R 1 1
C C14 -0.0068(2) 0.34540(14) 0.90434(13) 0.0169(3) Uani d . 1 1
H H14 0.0697 0.4116 0.9595 0.020 Uiso calc R 1 1
O O2 -0.34498(17) 0.04884(11) 0.67328(10) 0.0236(3) Uani d . 1 1
C C15 -0.2488(3) 0.00094(16) 0.57046(14) 0.0243(3) Uani d . 1 1
H H15C -0.2194 0.0732 0.5197 0.037 Uiso calc R 1 1
H H15A -0.3473 -0.0710 0.5274 0.037 Uiso calc R 1 1
H H15B -0.1138 -0.0322 0.5937 0.037 Uiso calc R 1 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
O1 C1 N1 123.20(13)
O1 C1 C3 122.98(12)
N1 C1 C3 113.82(12)
C1 N1 C2 127.64(12)
C1 N1 H1 116.2
C2 N1 H1 116.2
N2 C2 N1 115.74(12)
N2 C2 S1 127.15(11)
N1 C2 S1 117.08(11)
C2 N2 C9 129.80(12)
C2 N2 H2 115.1
C9 N2 H2 115.1
C4 C3 C8 118.29(13)
C4 C3 C1 121.86(13)
C8 C3 C1 119.84(13)
C5 C4 C3 120.81(14)
C5 C4 Cl1 117.49(12)
C3 C4 Cl1 121.67(11)
C6 C5 C4 120.05(14)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C7 120.15(14)
C5 C6 H6 119.9
C7 C6 H6 119.9
C6 C7 C8 119.81(15)
C6 C7 H7 120.1
C8 C7 H7 120.1
C7 C8 C3 120.88(14)
C7 C8 H8 119.6
C3 C8 H8 119.6
C14 C9 C10 120.87(13)
C14 C9 N2 115.32(12)
C10 C9 N2 123.81(13)
C11 C10 C9 118.42(13)
C11 C10 H10 120.8
C9 C10 H10 120.8
O2 C11 C12 115.39(13)
O2 C11 C10 123.32(13)
C12 C11 C10 121.30(13)
C13 C12 C11 119.29(13)
C13 C12 H12 120.4
C11 C12 H12 120.4
C12 C13 C14 120.44(13)
C12 C13 H13 119.8
C14 C13 H13 119.8
C9 C14 C13 119.61(13)
C9 C14 H14 120.2
C13 C14 H14 120.2
C11 O2 C15 117.13(12)
O2 C15 H15C 109.5
O2 C15 H15A 109.5
H15C C15 H15A 109.5
O2 C15 H15B 109.5
H15C C15 H15B 109.5
H15A C15 H15B 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2213(18)
C1 N1 1.3862(18)
C1 C3 1.5007(19)
N1 C2 1.3981(18)
N1 H1 0.8800
C2 N2 1.3334(19)
C2 S1 1.6758(16)
N2 C9 1.4243(18)
N2 H2 0.8800
C3 C4 1.401(2)
C3 C8 1.401(2)
C4 C5 1.389(2)
C4 Cl1 1.7370(16)
C5 C6 1.387(2)
C5 H5 0.9500
C6 C7 1.388(2)
C6 H6 0.9500
C7 C8 1.392(2)
C7 H7 0.9500
C8 H8 0.9500
C9 C14 1.392(2)
C9 C10 1.3948(19)
C10 C11 1.394(2)
C10 H10 0.9500
C11 O2 1.3713(17)
C11 C12 1.394(2)
C12 C13 1.385(2)
C12 H12 0.9500
C13 C14 1.393(2)
C13 H13 0.9500
C14 H14 0.9500
O2 C15 1.4288(19)
C15 H15C 0.9800
C15 H15A 0.9800
C15 H15B 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
N2 H2 O1 . 0.88 1.95 2.6500(17) 135
N1 H1 S1 2_666 0.88 2.64 3.4080(17) 146
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
O1 C1 N1 C2 6.0(2)
C3 C1 N1 C2 -174.52(13)
C1 N1 C2 N2 -8.8(2)
C1 N1 C2 S1 169.20(12)
N1 C2 N2 C9 169.91(13)
S1 C2 N2 C9 -7.9(2)
O1 C1 C3 C4 -39.5(2)
N1 C1 C3 C4 141.05(14)
O1 C1 C3 C8 139.31(15)
N1 C1 C3 C8 -40.16(18)
C8 C3 C4 C5 -0.1(2)
C1 C3 C4 C5 178.72(13)
C8 C3 C4 Cl1 177.95(11)
C1 C3 C4 Cl1 -3.24(19)
C3 C4 C5 C6 0.1(2)
Cl1 C4 C5 C6 -178.03(12)
C4 C5 C6 C7 0.1(2)
C5 C6 C7 C8 -0.3(2)
C6 C7 C8 C3 0.3(2)
C4 C3 C8 C7 -0.1(2)
C1 C3 C8 C7 -178.91(13)
C2 N2 C9 C14 -151.59(15)
C2 N2 C9 C10 28.9(2)
C14 C9 C10 C11 2.3(2)
N2 C9 C10 C11 -178.27(13)
C9 C10 C11 O2 -179.88(14)
C9 C10 C11 C12 -0.2(2)
O2 C11 C12 C13 177.99(13)
C10 C11 C12 C13 -1.7(2)
C11 C12 C13 C14 1.6(2)
C10 C9 C14 C13 -2.4(2)
N2 C9 C14 C13 178.10(13)
C12 C13 C14 C9 0.4(2)
C12 C11 O2 C15 -176.82(14)
C10 C11 O2 C15 2.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 770004
