#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/43/2204399.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_2204399
loop_
_publ_author_name
'M. Sukeri M. Yusof'
'Bohari M. Yamin'
_publ_section_title
;
 N-(4-Methoxybenzoyl)-N'-o-tolylthiourea
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1687
_journal_page_last               o1688
_journal_paper_doi               10.1107/S1600536804021373
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H16 N2 O2 S'
_chemical_formula_moiety         'C16 H16 N2 O2 S'
_chemical_formula_sum            'C16 H16 N2 O2 S'
_chemical_formula_weight         300.37
_chemical_name_systematic
;
N-(p-Methoxybenzoyl)-N'-o-tolylthiourea
;
_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                94.492(3)
_cell_angle_beta                 102.639(3)
_cell_angle_gamma                113.064(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4923(14)
_cell_length_b                   7.7866(14)
_cell_length_c                   14.406(3)
_cell_measurement_reflns_used    893
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.9
_cell_volume                     741.8(2)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT and SADABS (Sheldrick, 1996)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_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  0.013
_diffrn_reflns_av_sigmaI/netI    0.014
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7569
_diffrn_reflns_theta_full        26.0
_diffrn_reflns_theta_max         26.0
_diffrn_reflns_theta_min         2.9
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.22
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.49
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.21
_refine_ls_extinction_coef       0.023(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.041
_refine_ls_R_factor_gt           0.038
_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)+(0.0615P)²+0.1424P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.107
_refine_ls_wR_factor_ref         0.110
_reflns_number_gt                2681
_reflns_number_total             2896
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wk6026.cif
_cod_data_source_block           I
_cod_database_code               2204399
_cod_database_fobs_code          2204399
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
S1 0.39806(7) 1.00233(5) 0.85178(3) 0.05868(17) Uani d . 1 S
O1 0.1883(2) 0.37063(15) 0.84889(8) 0.0645(3) Uani d . 1 O
O2 0.1875(2) 0.26807(18) 1.27889(8) 0.0701(4) Uani d . 1 O
N1 0.30212(18) 0.68141(17) 0.91595(9) 0.0468(3) Uani d . 1 N
H1 0.3386 0.7570 0.9702 0.056 Uiso calc R 1 H
N2 0.2637(2) 0.64815(17) 0.75211(9) 0.0497(3) Uani d . 1 N
H2 0.2214 0.5304 0.7572 0.060 Uiso calc R 1 H
C1 0.2280(2) 0.5559(2) 1.09465(11) 0.0482(3) Uani d . 1 C
H1A 0.2369 0.6767 1.0884 0.058 Uiso calc R 1 H
C2 0.2142(2) 0.4944(2) 1.18054(11) 0.0540(4) Uani d . 1 C
H2A 0.2147 0.5743 1.2322 0.065 Uiso calc R 1 H
C3 0.1994(2) 0.3142(2) 1.19100(11) 0.0514(4) Uani d . 1 C
C4 0.1976(3) 0.1951(2) 1.11394(12) 0.0561(4) Uani d . 1 C
H4 0.1868 0.0737 1.1201 0.067 Uiso calc R 1 H
C5 0.2118(2) 0.2583(2) 1.02783(12) 0.0535(4) Uani d . 1 C
H5 0.2099 0.1779 0.9760 0.064 Uiso calc R 1 H
C6 0.2289(2) 0.4388(2) 1.01674(10) 0.0450(3) Uani d . 1 C
C7 0.2377(2) 0.4916(2) 0.92097(11) 0.0475(3) Uani d . 1 C
C8 0.3164(2) 0.7678(2) 0.83517(10) 0.0437(3) Uani d . 1 C
C9 0.2656(2) 0.6825(2) 0.65711(10) 0.0467(3) Uani d . 1 C
C10 0.2758(2) 0.5425(2) 0.59439(11) 0.0523(4) Uani d . 1 C
C11 0.2752(3) 0.5703(3) 0.50043(13) 0.0667(5) Uani d . 1 C
H11 0.2811 0.4784 0.4575 0.080 Uiso calc R 1 H
C12 0.2663(3) 0.7282(3) 0.46900(13) 0.0752(5) Uani d . 1 C
H12 0.2683 0.7441 0.4058 0.090 Uiso calc R 1 H
C13 0.2546(3) 0.8634(3) 0.53120(13) 0.0735(5) Uani d . 1 C
H13 0.2483 0.9712 0.5101 0.088 Uiso calc R 1 H
C14 0.2520(3) 0.8405(2) 0.62495(12) 0.0611(4) Uani d . 1 C
H14 0.2411 0.9313 0.6664 0.073 Uiso calc R 1 H
C15 0.1679(3) 0.0833(3) 1.29285(16) 0.0797(6) Uani d . 1 C
H15A 0.0486 -0.0102 1.2470 0.120 Uiso calc R 1 H
H15B 0.1579 0.0684 1.3573 0.120 Uiso calc R 1 H
H15C 0.2838 0.0670 1.2837 0.120 Uiso calc R 1 H
C16 0.2865(3) 0.3668(3) 0.62586(14) 0.0706(5) Uani d . 1 C
H16A 0.3934 0.4017 0.6842 0.106 Uiso calc R 1 H
H16B 0.3121 0.2978 0.5760 0.106 Uiso calc R 1 H
H16C 0.1608 0.2884 0.6375 0.106 Uiso calc R 1 H
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
_geom_angle_publ_flag
C3 O2 C15 118.04(15) ?
C7 N1 C8 128.91(12) ?
C7 N1 H1 115.5 ?
C8 N1 H1 115.5 ?
C8 N2 C9 130.91(12) ?
C8 N2 H2 114.5 ?
C9 N2 H2 114.5 ?
C2 C1 C6 120.53(14) ?
C2 C1 H1A 119.7 ?
C6 C1 H1A 119.7 ?
C1 C2 C3 120.55(14) ?
C1 C2 H2A 119.7 ?
C3 C2 H2A 119.7 ?
O2 C3 C4 124.54(15) ?
O2 C3 C2 115.76(15) ?
C4 C3 C2 119.70(14) ?
C5 C4 C3 119.31(15) ?
C5 C4 H4 120.3 ?
C3 C4 H4 120.3 ?
C4 C5 C6 121.59(15) ?
C4 C5 H5 119.2 ?
C6 C5 H5 119.2 ?
C5 C6 C1 118.31(13) ?
C5 C6 C7 117.57(13) ?
C1 C6 C7 124.05(13) ?
O1 C7 N1 121.55(14) ?
O1 C7 C6 121.17(14) ?
N1 C7 C6 117.27(12) ?
N2 C8 N1 114.51(12) yes
N2 C8 S1 127.60(11) yes
N1 C8 S1 117.89(10) yes
C14 C9 C10 120.40(14) ?
C14 C9 N2 123.44(13) ?
C10 C9 N2 116.14(13) ?
C11 C10 C9 117.65(15) ?
C11 C10 C16 120.26(15) ?
C9 C10 C16 122.09(15) ?
C12 C11 C10 122.13(16) ?
C12 C11 H11 118.9 ?
C10 C11 H11 118.9 ?
C11 C12 C13 119.47(17) ?
C11 C12 H12 120.3 ?
C13 C12 H12 120.3 ?
C12 C13 C14 120.41(17) ?
C12 C13 H13 119.8 ?
C14 C13 H13 119.8 ?
C13 C14 C9 119.91(16) ?
C13 C14 H14 120.0 ?
C9 C14 H14 120.0 ?
O2 C15 H15A 109.5 ?
O2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C10 C16 H16A 109.5 ?
C10 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C10 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 1.6608(15) yes
O1 C7 1.2282(18) yes
O2 C3 1.3549(19) ?
O2 C15 1.423(2) ?
N1 C7 1.3767(18) yes
N1 C8 1.3925(19) yes
N1 H1 0.8600 ?
N2 C8 1.3365(18) yes
N2 C9 1.4170(19) yes
N2 H2 0.8600 ?
C1 C2 1.371(2) ?
C1 C6 1.392(2) ?
C1 H1A 0.9300 ?
C2 C3 1.387(2) ?
C2 H2A 0.9300 ?
C3 C4 1.384(2) ?
C4 C5 1.380(2) ?
C4 H4 0.9300 ?
C5 C6 1.386(2) ?
C5 H5 0.9300 ?
C6 C7 1.478(2) ?
C9 C14 1.380(2) ?
C9 C10 1.397(2) ?
C10 C11 1.387(2) ?
C10 C16 1.500(2) ?
C11 C12 1.363(3) ?
C11 H11 0.9300 ?
C12 C13 1.371(3) ?
C12 H12 0.9300 ?
C13 C14 1.379(2) ?
C13 H13 0.9300 ?
C14 H14 0.9300 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
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
C14 H14 S1 1_555 0.93 2.59 3.1895(18) 123 yes
N2 H2 O1 1_555 0.86 1.87 2.6063(17) 142 yes
N1 H1 S1 2_677 0.86 2.85 3.6596(15) 158 yes
C1 H1A S1 2_677 0.93 2.78 3.3712(17) 122 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130389
