#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/11/2231178.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_2231178
loop_
_publ_author_name
'Md Nasir, Mohd Faizal'
'Hassan, Ibrahim N.'
'M. Yamin, Bohari'
'Daud, W. R. W'
'Kassim, Mohammad B.'
_publ_section_title
;
 3-(3-Methoxybenzoyl)-1,1-diphenylthiourea
;
_journal_coeditor_code           JH2306
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1947
_journal_page_last               o1948
_journal_paper_doi               10.1107/S1600536811025785
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H18 N2 O2 S'
_chemical_formula_moiety         'C21 H18 N2 O2 S'
_chemical_formula_sum            'C21 H18 N2 O2 S'
_chemical_formula_weight         362.43
_chemical_melting_point_gt       412.15
_chemical_melting_point_lt       410.15
_chemical_name_systematic
;
3-(3-Methoxybenzoyl)-1,1-diphenylthiourea
;
_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                112.796(9)
_cell_angle_beta                 100.336(10)
_cell_angle_gamma                97.951(10)
_cell_formula_units_Z            2
_cell_length_a                   6.056(3)
_cell_length_b                   12.895(7)
_cell_length_c                   13.344(7)
_cell_measurement_reflns_used    3612
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      55.182
_cell_measurement_theta_min      6.396
_cell_volume                     919.9(8)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10189
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_correction_T_min  0.9062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0379
_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)+(0.0578P)²+0.1546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                2663
_reflns_number_total             3612
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jh2306.cif
_cod_data_source_block           I
_cod_original_cell_volume        920.0(8)
_cod_database_code               2231178
_cod_database_fobs_code          2231178
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
S S1 0.28578(10) 0.32442(4) 0.43411(4) 0.05684(19) Uani d . 1 1
O O1 0.0958(3) 0.92764(11) 0.40494(14) 0.0667(4) Uani d . 1 1
O O2 -0.0666(2) 0.49768(10) 0.27758(12) 0.0554(4) Uani d . 1 1
N N1 0.2897(3) 0.47668(11) 0.34630(12) 0.0403(4) Uani d . 1 1
N N2 0.0990(2) 0.28974(11) 0.22465(10) 0.0372(3) Uani d . 1 1
C C6 0.4600(3) 0.67429(15) 0.30353(15) 0.0458(4) Uani d . 1 1
H H6 0.5408 0.6164 0.2821 0.055 Uiso calc R 1 1
C C5 0.5442(3) 0.78217(16) 0.30918(17) 0.0504(5) Uani d . 1 1
H H5 0.6817 0.7962 0.2898 0.060 Uiso calc R 1 1
C C4 0.4287(3) 0.86899(15) 0.34293(15) 0.0458(4) Uani d . 1 1
H H4 0.4889 0.9413 0.3471 0.055 Uiso calc R 1 1
C C3 0.2235(3) 0.84874(14) 0.37065(15) 0.0438(4) Uani d . 1 1
C C2 0.1354(3) 0.74050(14) 0.36416(14) 0.0430(4) Uani d . 1 1
H H2 -0.0031 0.7264 0.3827 0.052 Uiso calc R 1 1
C C1 0.2519(3) 0.65424(13) 0.33049(13) 0.0380(4) Uani d . 1 1
C C21 0.1482(4) 1.03154(16) 0.39139(19) 0.0595(5) Uani d . 1 1
H H21A 0.2992 1.0754 0.4378 0.089 Uiso calc R 1 1
H H21B 0.0366 1.0762 0.4132 0.089 Uiso calc R 1 1
H H21C 0.1443 1.0132 0.3141 0.089 Uiso calc R 1 1
C C7 0.1389(3) 0.53717(14) 0.31542(14) 0.0405(4) Uani d . 1 1
C C8 0.2192(3) 0.36345(13) 0.33048(13) 0.0376(4) Uani d . 1 1
C C9 0.1204(3) 0.31150(13) 0.12858(13) 0.0369(4) Uani d . 1 1
C C14 -0.0742(3) 0.29310(16) 0.04667(14) 0.0476(4) Uani d . 1 1
H H14 -0.2192 0.2659 0.0529 0.057 Uiso calc R 1 1
C C13 -0.0526(4) 0.31537(19) -0.04475(16) 0.0610(6) Uani d . 1 1
H H13 -0.1836 0.3029 -0.1002 0.073 Uiso calc R 1 1
C C12 0.1610(4) 0.35575(19) -0.05447(17) 0.0618(6) Uani d . 1 1
H H12 0.1745 0.3719 -0.1155 0.074 Uiso calc R 1 1
C C11 0.3535(4) 0.37199(18) 0.02626(18) 0.0579(5) Uani d . 1 1
H H11 0.4983 0.3987 0.0195 0.070 Uiso calc R 1 1
C C10 0.3355(3) 0.34923(15) 0.11738(15) 0.0464(4) Uani d . 1 1
H H10 0.4675 0.3592 0.1712 0.056 Uiso calc R 1 1
C C15 -0.0664(3) 0.18826(13) 0.20578(13) 0.0388(4) Uani d . 1 1
C C16 -0.2480(3) 0.20071(17) 0.25501(16) 0.0523(5) Uani d . 1 1
H H16 -0.2582 0.2736 0.3035 0.063 Uiso calc R 1 1
C C17 -0.4148(4) 0.1046(2) 0.2320(2) 0.0697(6) Uani d . 1 1
H H17 -0.5374 0.1125 0.2654 0.084 Uiso calc R 1 1
C C18 -0.4001(4) -0.0022(2) 0.16034(19) 0.0757(8) Uani d . 1 1
H H18 -0.5141 -0.0668 0.1442 0.091 Uiso calc R 1 1
C C19 -0.2184(4) -0.01469(17) 0.11210(17) 0.0691(7) Uani d . 1 1
H H19 -0.2089 -0.0879 0.0640 0.083 Uiso calc R 1 1
C C20 -0.0481(4) 0.08113(14) 0.13453(14) 0.0505(5) Uani d . 1 1
H H20 0.0756 0.0729 0.1020 0.061 Uiso calc R 1 1
H H1A 0.416(3) 0.5170(16) 0.3974(17) 0.049(5) Uiso d . 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O1 C21 118.49(16)
C8 N1 C7 122.68(15)
C8 N1 H1A 116.5(13)
C7 N1 H1A 117.1(13)
C8 N2 C9 122.38(13)
C8 N2 C15 119.92(13)
C9 N2 C15 117.62(12)
C5 C6 C1 118.54(17)
C5 C6 H6 120.7
C1 C6 H6 120.7
C4 C5 C6 121.22(18)
C4 C5 H5 119.4
C6 C5 H5 119.4
C5 C4 C3 119.88(16)
C5 C4 H4 120.1
C3 C4 H4 120.1
O1 C3 C4 124.89(15)
O1 C3 C2 115.53(16)
C4 C3 C2 119.57(17)
C1 C2 C3 120.20(17)
C1 C2 H2 119.9
C3 C2 H2 119.9
C2 C1 C6 120.58(15)
C2 C1 C7 117.72(16)
C6 C1 C7 121.53(16)
O1 C21 H21A 109.5
O1 C21 H21B 109.5
H21A C21 H21B 109.5
O1 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
O2 C7 N1 123.01(15)
O2 C7 C1 122.65(16)
N1 C7 C1 114.33(15)
N2 C8 N1 114.68(14)
N2 C8 S1 124.04(12)
N1 C8 S1 121.26(12)
C14 C9 C10 119.92(16)
C14 C9 N2 119.86(15)
C10 C9 N2 120.21(15)
C9 C14 C13 119.56(18)
C9 C14 H14 120.2
C13 C14 H14 120.2
C12 C13 C14 120.52(19)
C12 C13 H13 119.7
C14 C13 H13 119.7
C11 C12 C13 119.54(18)
C11 C12 H12 120.2
C13 C12 H12 120.2
C12 C11 C10 120.76(19)
C12 C11 H11 119.6
C10 C11 H11 119.6
C11 C10 C9 119.66(18)
C11 C10 H10 120.2
C9 C10 H10 120.2
C20 C15 C16 120.88(16)
C20 C15 N2 119.82(16)
C16 C15 N2 119.20(16)
C15 C16 C17 119.6(2)
C15 C16 H16 120.2
C17 C16 H16 120.2
C18 C17 C16 120.1(2)
C18 C17 H17 120.0
C16 C17 H17 120.0
C17 C18 C19 120.30(19)
C17 C18 H18 119.9
C19 C18 H18 119.9
C18 C19 C20 120.5(2)
C18 C19 H19 119.8
C20 C19 H19 119.8
C15 C20 C19 118.6(2)
C15 C20 H20 120.7
C19 C20 H20 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.6503(17)
O1 C3 1.351(2)
O1 C21 1.421(2)
O2 C7 1.210(2)
N1 C8 1.384(2)
N1 C7 1.387(2)
N1 H1A 0.87(2)
N2 C8 1.352(2)
N2 C9 1.438(2)
N2 C15 1.439(2)
C6 C5 1.382(2)
C6 C1 1.389(3)
C6 H6 0.9300
C5 C4 1.373(3)
C5 H5 0.9300
C4 C3 1.378(3)
C4 H4 0.9300
C3 C2 1.387(2)
C2 C1 1.371(3)
C2 H2 0.9300
C1 C7 1.489(2)
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C9 C14 1.378(2)
C9 C10 1.381(3)
C14 C13 1.381(3)
C14 H14 0.9300
C13 C12 1.373(3)
C13 H13 0.9300
C12 C11 1.368(3)
C12 H12 0.9300
C11 C10 1.375(3)
C11 H11 0.9300
C10 H10 0.9300
C15 C20 1.374(3)
C15 C16 1.376(3)
C16 C17 1.377(3)
C16 H16 0.9300
C17 C18 1.365(4)
C17 H17 0.9300
C18 C19 1.369(4)
C18 H18 0.9300
C19 C20 1.389(3)
C19 H19 0.9300
C20 H20 0.9300
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
N1 H1A S1 2_666 0.87(2) 2.54(2) 3.380(2) 163.6(17) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656855
