##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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/  #
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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2004-08-17
_journal_date_accepted     2004-10-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue     11
_journal_page_first     o1998
_journal_page_last     o1999
_journal_paper_category     EO
_publ_contact_author_name     'Prof. Bohari M. Yamin'
_publ_contact_author_address
;
      X-ray Crystallography Labotary
      School of Chemical Sciences and Food Technology
      Universiti Kebangsaan Malaysia
      43600 Bangi, Selangor
      MALAYSIA
;
_publ_contact_author_email     bohari@pkrisc.cc.ukm.my
_publ_contact_author_fax     '6 03 89212410 '
_publ_contact_author_phone     '6 03 89213880'
_publ_section_title
;
N-(2-Chlorophenyl)-N-(4-methoxybenzoyl)thiourea
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'M. Sukeri M. Yusof' ?
;
School of Chemical Sciences and Food Technology
Universiti Kebangsaan Malaysia
43600 Bangi
Selangor
Malaysia
;
    'Bohari M. Yamin' ?
;
School of Chemical Sciences and Food Technology
Universiti Kebangsaan Malaysia
43600 Bangi
Selangor
Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-(2-Chlorophenyl)-N-(4-methoxybenzoyl)thiourea
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H13 Cl N2 O2 S'
_chemical_formula_sum     'C15 H13 Cl N2 O2 S'
_chemical_formula_iupac     'C15 H13 Cl N2 O2 S'
_chemical_formula_weight     320.78
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
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     13.438(3)
_cell_length_b     3.9893(9)
_cell_length_c     27.727(6)
_cell_angle_alpha     90.00
_cell_angle_beta     99.508(4)
_cell_angle_gamma     90.00
_cell_volume     1466.0(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2167
_cell_measurement_theta_min     1.50
_cell_measurement_theta_max     27.0
_cell_measurement_temperature     273(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.453
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.408
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9156
_exptl_absorpt_correction_T_max     0.9376
_exptl_special_details
;
;
_diffrn_ambient_temperature     273(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     83.66
_diffrn_reflns_number     7879
_diffrn_reflns_av_R_equivalents     0.0236
_diffrn_reflns_av_sigmaI/netI     0.0302
_diffrn_reflns_theta_min     1.49
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.0
_diffrn_measured_fraction_theta_max     0.99
_diffrn_measured_fraction_theta_full     0.99
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -5
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -35
_diffrn_reflns_limit_l_max     27
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
;
_reflns_number_total     3162
_reflns_number_gt     2649
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.074
_refine_ls_R_factor_gt     0.059
_refine_ls_wR_factor_gt     0.133
_refine_ls_wR_factor_ref     0.140
_refine_ls_goodness_of_fit_ref     1.19
_refine_ls_restrained_S_all     1.19
_refine_ls_number_reflns     3162
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0589P)²+0.3777P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.33
_refine_diff_density_min     -0.18
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXTL (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 1997)'
_computing_molecular_graphics     SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Cl1 0.41573(6) -0.2117(2) 0.04847(3) 0.0738(3) Uani d . 1 . . Cl
    S1 0.19169(4) -0.16876(18) 0.18381(2) 0.0447(2) Uani d . 1 . . S
    O1 0.51528(14) 0.1285(6) 0.17833(7) 0.0692(6) Uani d . 1 . . O
    O2 0.74579(13) -0.0232(6) 0.39513(6) 0.0591(5) Uani d . 1 . . O
    N1 0.38261(14) -0.0358(6) 0.21388(7) 0.0447(5) Uani d . 1 . . N
    H1 0.3662 -0.0932 0.2414 0.054 Uiso calc R 1 . . H
    N2 0.32877(15) 0.0564(6) 0.13186(7) 0.0461(5) Uani d . 1 . . N
    H2 0.3907 0.1115 0.1321 0.055 Uiso calc R 1 . . H
    C1 0.52146(17) -0.1171(6) 0.30500(9) 0.0431(6) Uani d . 1 . . C
    H1A 0.4575 -0.2097 0.3034 0.052 Uiso calc R 1 . . H
    C2 0.58848(19) -0.1278(7) 0.34809(9) 0.0479(6) Uani d . 1 . . C
    H2A 0.5693 -0.2264 0.3755 0.057 Uiso calc R 1 . . H
    C3 0.68438(17) 0.0068(7) 0.35105(8) 0.0425(6) Uani d . 1 . . C
    C4 0.71249(18) 0.1590(7) 0.31041(9) 0.0434(6) Uani d . 1 . . C
    H4 0.7762 0.2540 0.3122 0.052 Uiso calc R 1 . . H
    C5 0.64447(17) 0.1672(7) 0.26735(9) 0.0435(6) Uani d . 1 . . C
    H5 0.6636 0.2670 0.2400 0.052 Uiso calc R 1 . . H
    C6 0.54857(17) 0.0317(6) 0.26356(8) 0.0391(5) Uani d . 1 . . C
    C7 0.48254(18) 0.0471(7) 0.21546(9) 0.0456(6) Uani d . 1 . . C
    C8 0.30453(17) -0.0402(6) 0.17439(8) 0.0394(5) Uani d . 1 . . C
    C9 0.26362(18) 0.0783(6) 0.08634(8) 0.0410(6) Uani d . 1 . . C
    C10 0.29672(19) -0.0371(7) 0.04432(9) 0.0484(6) Uani d . 1 . . C
    C11 0.2368(2) -0.0077(8) -0.00068(9) 0.0596(7) Uani d . 1 . . C
    H11 0.2599 -0.0835 -0.0286 0.072 Uiso calc R 1 . . H
    C12 0.1427(2) 0.1335(9) -0.00446(10) 0.0639(8) Uani d . 1 . . C
    H12 0.1018 0.1509 -0.0349 0.077 Uiso calc R 1 . . H
    C13 0.1088(2) 0.2491(8) 0.03648(10) 0.0591(8) Uani d . 1 . . C
    H13 0.0449 0.3437 0.0338 0.071 Uiso calc R 1 . . H
    C14 0.16971(19) 0.2252(7) 0.08169(9) 0.0495(6) Uani d . 1 . . C
    H14 0.1471 0.3090 0.1092 0.059 Uiso calc R 1 . . H
    C15 0.8456(2) 0.1038(9) 0.39970(10) 0.0648(9) Uani d . 1 . . C
    H15A 0.8808 -0.0104 0.3771 0.097 Uiso calc R 1 . . H
    H15B 0.8801 0.0681 0.4325 0.097 Uiso calc R 1 . . H
    H15C 0.8433 0.3394 0.3926 0.097 Uiso calc R 1 . . H
_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
    Cl1 C10 . 1.731(3) yes
    S1 C8 . 1.662(2) yes
    O1 C7 . 1.228(3) ?
    O2 C3 . 1.362(3) ?
    O2 C15 . 1.419(3) ?
    N1 C7 . 1.377(3) yes
    N1 C8 . 1.386(3) yes
    N1 H1 . 0.8600 ?
    N2 C8 . 1.331(3) yes
    N2 C9 . 1.415(3) yes
    N2 H2 . 0.8600 ?
    C1 C2 . 1.373(3) ?
    C1 C6 . 1.394(3) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.386(3) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.386(3) ?
    C4 C5 . 1.379(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.385(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.476(3) ?
    C9 C14 . 1.378(3) ?
    C9 C10 . 1.392(3) ?
    C10 C11 . 1.374(4) ?
    C11 C12 . 1.372(4) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.371(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.382(4) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
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
    C3 O2 C15 . . 118.2(2) ?
    C7 N1 C8 . . 129.5(2) ?
    C7 N1 H1 . . 115.3 ?
    C8 N1 H1 . . 115.3 ?
    C8 N2 C9 . . 127.0(2) ?
    C8 N2 H2 . . 116.5 ?
    C9 N2 H2 . . 116.5 ?
    C2 C1 C6 . . 120.5(2) ?
    C2 C1 H1A . . 119.8 ?
    C6 C1 H1A . . 119.8 ?
    C1 C2 C3 . . 120.6(2) ?
    C1 C2 H2A . . 119.7 ?
    C3 C2 H2A . . 119.7 ?
    O2 C3 C2 . . 116.0(2) ?
    O2 C3 C4 . . 124.2(2) ?
    C2 C3 C4 . . 119.8(2) ?
    C5 C4 C3 . . 118.9(2) ?
    C5 C4 H4 . . 120.5 ?
    C3 C4 H4 . . 120.5 ?
    C4 C5 C6 . . 122.1(2) ?
    C4 C5 H5 . . 118.9 ?
    C6 C5 H5 . . 118.9 ?
    C5 C6 C1 . . 118.0(2) ?
    C5 C6 C7 . . 117.7(2) ?
    C1 C6 C7 . . 124.2(2) ?
    O1 C7 N1 . . 121.3(2) ?
    O1 C7 C6 . . 121.6(2) ?
    N1 C7 C6 . . 117.2(2) ?
    N2 C8 N1 . . 115.6(2) ?
    N2 C8 S1 . . 126.28(18) ?
    N1 C8 S1 . . 118.11(16) ?
    C14 C9 C10 . . 118.5(2) ?
    C14 C9 N2 . . 122.1(2) ?
    C10 C9 N2 . . 119.3(2) ?
    C11 C10 C9 . . 120.8(3) ?
    C11 C10 Cl1 . . 119.4(2) ?
    C9 C10 Cl1 . . 119.80(19) ?
    C12 C11 C10 . . 119.9(3) ?
    C12 C11 H11 . . 120.0 ?
    C10 C11 H11 . . 120.0 ?
    C13 C12 C11 . . 120.2(2) ?
    C13 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C12 C13 C14 . . 120.0(3) ?
    C12 C13 H13 . . 120.0 ?
    C14 C13 H13 . . 120.0 ?
    C9 C14 C13 . . 120.7(3) ?
    C9 C14 H14 . . 119.7 ?
    C13 C14 H14 . . 119.7 ?
    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 ?
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
    C6 C1 C2 C3 . . . . -0.4(4) ?
    C15 O2 C3 C2 . . . . 178.6(3) ?
    C15 O2 C3 C4 . . . . -1.2(4) ?
    C1 C2 C3 O2 . . . . -178.6(2) ?
    C1 C2 C3 C4 . . . . 1.1(4) ?
    O2 C3 C4 C5 . . . . 178.5(2) ?
    C2 C3 C4 C5 . . . . -1.2(4) ?
    C3 C4 C5 C6 . . . . 0.8(4) ?
    C4 C5 C6 C1 . . . . -0.1(4) ?
    C4 C5 C6 C7 . . . . -178.6(2) ?
    C2 C1 C6 C5 . . . . -0.1(4) ?
    C2 C1 C6 C7 . . . . 178.4(2) ?
    C8 N1 C7 O1 . . . . -1.1(5) ?
    C8 N1 C7 C6 . . . . 179.3(2) ?
    C5 C6 C7 O1 . . . . 11.0(4) ?
    C1 C6 C7 O1 . . . . -167.4(3) ?
    C5 C6 C7 N1 . . . . -169.4(2) ?
    C1 C6 C7 N1 . . . . 12.2(4) ?
    C9 N2 C8 N1 . . . . -179.3(2) yes
    C9 N2 C8 S1 . . . . 1.8(4) ?
    C7 N1 C8 N2 . . . . -1.6(4) ?
    C7 N1 C8 S1 . . . . 177.4(2) yes
    C8 N2 C9 C14 . . . . 46.2(4) ?
    C8 N2 C9 C10 . . . . -137.0(3) ?
    C14 C9 C10 C11 . . . . -0.6(4) ?
    N2 C9 C10 C11 . . . . -177.5(3) ?
    C14 C9 C10 Cl1 . . . . 178.1(2) ?
    N2 C9 C10 Cl1 . . . . 1.2(3) ?
    C9 C10 C11 C12 . . . . -0.7(5) ?
    Cl1 C10 C11 C12 . . . . -179.3(2) ?
    C10 C11 C12 C13 . . . . 0.8(5) ?
    C11 C12 C13 C14 . . . . 0.4(5) ?
    C10 C9 C14 C13 . . . . 1.7(4) ?
    N2 C9 C14 C13 . . . . 178.5(2) ?
    C12 C13 C14 C9 . . . . -1.6(4) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    N2 H2 O1 . . 1_555 0.86 1.93 2.638(3) 138 yes
    C14 H14 S1 . . 1_555 0.93 2.80 3.209(3) 107 yes
    C1 H1A S1 . . 2_545 0.93 2.78 3.666(3) 159 yes
