##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
1-(3-Methoxyphenyl)-3-(4-methylbenzoyl)thiourea
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H16 N2 O2 S'
_chemical_formula_sum     'C16 H16 N2 O2 S'
_chemical_formula_iupac     'C16 H16 N2 O2 S'
_chemical_formula_weight     300.37
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     5.3031(6)
_cell_length_b     21.159(2)
_cell_length_c     13.2837(14)
_cell_angle_alpha     90.00
_cell_angle_beta     90.027(15)
_cell_angle_gamma     90.00
_cell_volume     1490.5(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1407
_cell_measurement_theta_min     2.49
_cell_measurement_theta_max     21.20
_cell_measurement_temperature     120(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.52
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.339
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     632
_exptl_absorpt_coefficient_mu     0.223
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2002)'
_exptl_absorpt_correction_T_min     0.8929
_exptl_absorpt_correction_T_max     0.9802
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     'Bruker SMART APEX'
_diffrn_measurement_method     'φ and ω'
_diffrn_reflns_number     12383
_diffrn_reflns_av_R_equivalents     0.0910
_diffrn_reflns_av_sigmaI/netI     0.1001
_diffrn_reflns_theta_min     1.81
_diffrn_reflns_theta_max     27.86
_diffrn_reflns_theta_full     27.86
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -27
_diffrn_reflns_limit_k_max     27
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     1438
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     430
_diffrn_standards_decay_%     0
_reflns_number_total     3535
_reflns_number_gt     2050
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0995
_refine_ls_R_factor_gt     0.0450
_refine_ls_wR_factor_gt     0.1030
_refine_ls_wR_factor_ref     0.1149
_refine_ls_goodness_of_fit_ref     0.879
_refine_ls_restrained_S_all     0.879
_refine_ls_number_reflns     3535
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'calc w = 1/[σ²(Fo²)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.324
_refine_diff_density_min     -0.327
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 2002)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Bruker, 2002)'
_computing_structure_refinement     'SHELXTL'
_computing_molecular_graphics     'SHELXTL'
_computing_publication_material     'SHELXTL'
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_disorder_assembly
    _atom_site_disorder_group
    S S1 0.32324(14) 1.01213(3) 0.85607(5) 0.0443(2) Uani d . 1 . .
    O O1 0.6061(3) 0.81054(7) 0.82493(11) 0.0427(5) Uani d . 1 . .
    O O2 0.0758(3) 0.86111(8) 0.42661(12) 0.0484(5) Uani d . 1 . .
    N N1 0.3031(3) 0.90015(8) 0.76221(13) 0.0325(5) Uani d . 1 . .
    H H1 0.3542 0.8606 0.7636 0.039 Uiso calc R 1 . .
    N N2 0.5727(3) 0.90797(8) 0.89643(13) 0.0326(5) Uani d . 1 . .
    H H2 0.6253 0.9309 0.9476 0.039 Uiso calc R 1 . .
    C C1 0.1346(4) 0.91542(10) 0.68283(16) 0.0302(5) Uani d . 1 . .
    C C2 -0.0701(5) 0.95549(10) 0.69401(18) 0.0371(6) Uani d . 1 . .
    H H2A -0.1001 0.9767 0.7559 0.044 Uiso calc R 1 . .
    C C3 -0.2299(5) 0.96387(11) 0.6126(2) 0.0447(7) Uani d . 1 . .
    H H3A -0.3706 0.9913 0.6194 0.054 Uiso calc R 1 . .
    C C4 -0.1907(5) 0.93341(11) 0.52169(19) 0.0421(7) Uani d . 1 . .
    H H4A -0.3028 0.9398 0.4668 0.050 Uiso calc R 1 . .
    C C5 0.0128(5) 0.89387(10) 0.51231(17) 0.0348(6) Uani d . 1 . .
    C C6 0.1752(4) 0.88476(9) 0.59290(17) 0.0321(6) Uani d . 1 . .
    H H6A 0.3154 0.8572 0.5860 0.039 Uiso calc R 1 . .
    C C7 -0.0996(5) 0.86212(13) 0.34504(18) 0.0579(8) Uani d . 1 . .
    H H7A -0.2651 0.8480 0.3689 0.087 Uiso calc R 1 . .
    H H7B -0.0407 0.8338 0.2916 0.087 Uiso calc R 1 . .
    H H7C -0.1132 0.9052 0.3187 0.087 Uiso calc R 1 . .
    C C8 0.3948(4) 0.93659(10) 0.83449(16) 0.0304(5) Uani d . 1 . .
    C C9 0.6782(5) 0.84850(10) 0.88869(16) 0.0322(5) Uani d . 1 . .
    C C10 0.8808(4) 0.83358(9) 0.96113(15) 0.0278(5) Uani d . 1 . .
    C C11 0.9470(5) 0.77047(10) 0.97489(16) 0.0360(6) Uani d . 1 . .
    H H11A 0.8625 0.7384 0.9378 0.043 Uiso calc R 1 . .
    C C12 1.1343(5) 0.75421(10) 1.04196(16) 0.0362(6) Uani d . 1 . .
    H H12A 1.1783 0.7110 1.0500 0.043 Uiso calc R 1 . .
    C C13 1.2603(4) 0.79982(10) 1.09818(15) 0.0317(5) Uani d . 1 . .
    C C14 1.1956(5) 0.86231(10) 1.08289(17) 0.0381(6) Uani d . 1 . .
    H H14A 1.2806 0.8943 1.1198 0.046 Uiso calc R 1 . .
    C C15 1.0105(4) 0.87923(10) 1.01519(16) 0.0342(6) Uani d . 1 . .
    H H15A 0.9714 0.9226 1.0055 0.041 Uiso calc R 1 . .
    C C16 1.4626(5) 0.78203(11) 1.17233(17) 0.0431(6) Uani d . 1 . .
    H H16A 1.6214 0.8024 1.1532 0.065 Uiso calc R 1 . .
    H H16B 1.4848 0.7360 1.1722 0.065 Uiso calc R 1 . .
    H H16C 1.4133 0.7960 1.2398 0.065 Uiso calc R 1 . .
_geom_special_details
;
 ?
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 C8 . 1.668(2) ?
    O1 C9 . 1.228(2) ?
    O2 C5 . 1.374(3) ?
    O2 C7 . 1.428(3) ?
    N1 C8 . 1.324(3) ?
    N1 C1 . 1.419(3) ?
    N1 H1 . 0.8800 no
    N2 C9 . 1.381(3) ?
    N2 C8 . 1.391(3) ?
    N2 H2 . 0.8800 no
    C1 C6 . 1.376(3) ?
    C1 C2 . 1.385(3) ?
    C2 C3 . 1.385(3) ?
    C2 H2A . 0.9500 no
    C3 C4 . 1.385(3) ?
    C3 H3A . 0.9500 no
    C4 C5 . 1.371(3) ?
    C4 H4A . 0.9500 no
    C5 C6 . 1.387(3) ?
    C6 H6A . 0.9500 no
    C7 H7A . 0.9800 no
    C7 H7B . 0.9800 no
    C7 H7C . 0.9800 no
    C9 C10 . 1.477(3) ?
    C10 C15 . 1.386(3) ?
    C10 C11 . 1.393(3) ?
    C11 C12 . 1.378(3) ?
    C11 H11A . 0.9500 no
    C12 C13 . 1.391(3) ?
    C12 H12A . 0.9500 no
    C13 C14 . 1.381(3) ?
    C13 C16 . 1.504(3) ?
    C14 C15 . 1.379(3) ?
    C14 H14A . 0.9500 no
    C15 H15A . 0.9500 no
    C16 H16A . 0.9800 no
    C16 H16B . 0.9800 no
    C16 H16C . 0.9800 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C5 O2 C7 . . 117.6(2) ?
    C8 N1 C1 . . 129.59(18) ?
    C8 N1 H1 . . 115.2 no
    C1 N1 H1 . . 115.2 no
    C9 N2 C8 . . 128.87(18) ?
    C9 N2 H2 . . 115.6 no
    C8 N2 H2 . . 115.6 no
    C6 C1 C2 . . 120.3(2) ?
    C6 C1 N1 . . 116.0(2) ?
    C2 C1 N1 . . 123.6(2) ?
    C3 C2 C1 . . 118.3(2) ?
    C3 C2 H2A . . 120.9 no
    C1 C2 H2A . . 120.9 no
    C2 C3 C4 . . 122.0(2) ?
    C2 C3 H3A . . 119.0 no
    C4 C3 H3A . . 119.0 no
    C5 C4 C3 . . 118.8(2) ?
    C5 C4 H4A . . 120.6 no
    C3 C4 H4A . . 120.6 no
    C4 C5 O2 . . 125.0(2) ?
    C4 C5 C6 . . 120.2(2) ?
    O2 C5 C6 . . 114.7(2) ?
    C1 C6 C5 . . 120.5(2) ?
    C1 C6 H6A . . 119.8 no
    C5 C6 H6A . . 119.8 no
    O2 C7 H7A . . 109.5 no
    O2 C7 H7B . . 109.5 no
    H7A C7 H7B . . 109.5 no
    O2 C7 H7C . . 109.5 no
    H7A C7 H7C . . 109.5 no
    H7B C7 H7C . . 109.5 no
    N1 C8 N2 . . 115.12(18) ?
    N1 C8 S1 . . 126.83(17) ?
    N2 C8 S1 . . 118.03(16) ?
    O1 C9 N2 . . 121.4(2) ?
    O1 C9 C10 . . 122.4(2) ?
    N2 C9 C10 . . 116.18(19) ?
    C15 C10 C11 . . 118.4(2) ?
    C15 C10 C9 . . 123.34(19) ?
    C11 C10 C9 . . 118.28(19) ?
    C12 C11 C10 . . 120.4(2) ?
    C12 C11 H11A . . 119.8 no
    C10 C11 H11A . . 119.8 no
    C11 C12 C13 . . 121.3(2) ?
    C11 C12 H12A . . 119.3 no
    C13 C12 H12A . . 119.3 no
    C14 C13 C12 . . 117.8(2) ?
    C14 C13 C16 . . 120.9(2) ?
    C12 C13 C16 . . 121.4(2) ?
    C15 C14 C13 . . 121.4(2) ?
    C15 C14 H14A . . 119.3 no
    C13 C14 H14A . . 119.3 no
    C14 C15 C10 . . 120.7(2) ?
    C14 C15 H15A . . 119.7 no
    C10 C15 H15A . . 119.7 no
    C13 C16 H16A . . 109.5 no
    C13 C16 H16B . . 109.5 no
    H16A C16 H16B . . 109.5 no
    C13 C16 H16C . . 109.5 no
    H16A C16 H16C . . 109.5 no
    H16B C16 H16C . . 109.5 no
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C8 N1 C1 C6 . . . . 144.9(2) no
    C8 N1 C1 C2 . . . . -39.0(3) no
    C6 C1 C2 C3 . . . . -0.3(3) no
    N1 C1 C2 C3 . . . . -176.2(2) no
    C1 C2 C3 C4 . . . . 0.2(3) no
    C2 C3 C4 C5 . . . . -0.1(4) no
    C3 C4 C5 O2 . . . . -179.4(2) no
    C3 C4 C5 C6 . . . . 0.1(3) no
    C7 O2 C5 C4 . . . . -8.0(3) no
    C7 O2 C5 C6 . . . . 172.4(2) no
    C2 C1 C6 C5 . . . . 0.4(3) no
    N1 C1 C6 C5 . . . . 176.56(19) no
    C4 C5 C6 C1 . . . . -0.3(3) no
    O2 C5 C6 C1 . . . . 179.32(18) no
    C1 N1 C8 N2 . . . . -175.1(2) no
    C1 N1 C8 S1 . . . . 3.5(4) no
    C9 N2 C8 N1 . . . . 4.8(3) no
    C9 N2 C8 S1 . . . . -173.97(18) no
    C8 N2 C9 O1 . . . . -5.4(4) no
    C8 N2 C9 C10 . . . . 174.6(2) no
    O1 C9 C10 C15 . . . . 162.5(2) no
    N2 C9 C10 C15 . . . . -17.5(3) no
    O1 C9 C10 C11 . . . . -16.7(3) no
    N2 C9 C10 C11 . . . . 163.3(2) no
    C15 C10 C11 C12 . . . . 1.0(3) no
    C9 C10 C11 C12 . . . . -179.7(2) no
    C10 C11 C12 C13 . . . . 0.6(4) no
    C11 C12 C13 C14 . . . . -1.5(4) no
    C11 C12 C13 C16 . . . . 179.2(2) no
    C12 C13 C14 C15 . . . . 0.8(4) no
    C16 C13 C14 C15 . . . . -180.0(2) no
    C13 C14 C15 C10 . . . . 0.9(4) no
    C11 C10 C15 C14 . . . . -1.7(3) no
    C9 C10 C15 C14 . . . . 179.1(2) no
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 S1 3_677 0.88 2.89 3.7376(19) 163.3
    N1 H1 O1 . 0.88 1.89 2.621(2) 139.5
data_global
_journal_date_recd_electronic     2007-05-31
_journal_date_accepted     2007-07-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      9
_journal_page_first     o3695
_journal_page_last     o3695
_journal_paper_category     QO
_journal_coeditor_code     CS2042
_publ_contact_author_name     'Dr Aamer Saeed'
_publ_contact_author_address
;
Department of Chemistry
Quaid-i-Azam University
Islamabad 45320
Pakistan
;
_publ_contact_author_email     aamersaeed@yahoo.com
_publ_contact_author_fax     '+92 51 2873869'
_publ_contact_author_phone     '+92 51 90642128'
_publ_section_title
;
1-(3-Methoxyphenyl)-3-(4-methylbenzoyl)thiourea
;
loop_
    _publ_author_name
    _publ_author_address
    'Saeed, Aamer'
;
Department of Chemistry
Quaid-i-Azam University
Islamabad 45320
Pakistan
;
    'Flörke, Ulrich'
;
Department Chemie
Fakultät für Naturwissenschaften
Universität Paderborn
Warburgerstrasse 100
D-33098 Paderborn
Germany
;
