##############################################################################
###                                                                        ###
###        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/  #
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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-(4-Nitrobenzoyl)-3-phenylthiourea
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 N3 O3 S'
_chemical_formula_sum     'C14 H11 N3 O3 S'
_chemical_formula_iupac     'C14 H11 N3 O3 S'
_chemical_formula_weight     301.32
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     8.2660(10)
_cell_length_b     12.1458(9)
_cell_length_c     13.6687(16)
_cell_angle_alpha     90.00
_cell_angle_beta     92.651(10)
_cell_angle_gamma     90.00
_cell_volume     1370.8(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3023
_cell_measurement_theta_min     3.5
_cell_measurement_theta_max     25.7
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     'light brown'
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.35
_exptl_crystal_size_min     0.33
_exptl_crystal_density_diffrn     1.460
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     624
_exptl_absorpt_coefficient_mu     0.250
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(MULABS; Spek, 2003; Blessing, 1995)'
_exptl_absorpt_correction_T_min     0.9154
_exptl_absorpt_correction_T_max     0.9221
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(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     'Stoe IPDSII two-circle'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7976
_diffrn_reflns_av_R_equivalents     0.0352
_diffrn_reflns_av_sigmaI/netI     0.0283
_diffrn_reflns_theta_min     3.67
_diffrn_reflns_theta_max     25.68
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2552
_reflns_number_gt     2189
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0423
_refine_ls_R_factor_gt     0.0338
_refine_ls_wR_factor_gt     0.0823
_refine_ls_wR_factor_ref     0.0863
_refine_ls_goodness_of_fit_ref     1.021
_refine_ls_restrained_S_all     1.021
_refine_ls_number_reflns     2552
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0429P)²+0.4301P] 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     0.179
_refine_diff_density_min     -0.268
_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     'X-AREA (Stoe & Cie, 2001)'
_computing_cell_refinement     'X-AREA'
_computing_data_reduction     'X-AREA'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003) and XP (Sheldrick, 1991)'
_computing_publication_material     SHELXL97
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 0.28377(6) 0.03643(3) 0.56649(4) 0.04069(15) Uani d . 1 . .
    O O1 0.43815(14) 0.35452(9) 0.41816(8) 0.0331(3) Uani d . 1 . .
    N N1 0.43245(16) 0.16919(11) 0.44820(10) 0.0276(3) Uani d . 1 . .
    H H1 0.468(2) 0.1061(18) 0.4329(14) 0.041(5) Uiso d . 1 . .
    N N2 0.28612(16) 0.25938(11) 0.56390(10) 0.0272(3) Uani d . 1 . .
    H H2 0.318(3) 0.3148(19) 0.5309(15) 0.048(6) Uiso d . 1 . .
    N N3 0.80042(19) 0.19139(16) 0.03823(11) 0.0458(4) Uani d . 1 . .
    O O3 0.8597(2) 0.27153(16) 0.00061(11) 0.0732(5) Uani d . 1 . .
    O O4 0.8076(2) 0.09774(16) 0.00561(11) 0.0710(5) Uani d . 1 . .
    C C1 0.47242(18) 0.25966(12) 0.39415(11) 0.0249(3) Uani d . 1 . .
    C C2 0.33267(18) 0.16213(12) 0.52899(11) 0.0264(3) Uani d . 1 . .
    C C11 0.55951(18) 0.23703(12) 0.30229(11) 0.0246(3) Uani d . 1 . .
    C C12 0.5533(2) 0.13494(13) 0.25513(11) 0.0297(3) Uani d . 1 . .
    H H12 0.4948 0.0760 0.2823 0.036 Uiso calc R 1 . .
    C C13 0.6324(2) 0.11912(15) 0.16862(12) 0.0347(4) Uani d . 1 . .
    H H13 0.6300 0.0497 0.1366 0.042 Uiso calc R 1 . .
    C C14 0.71447(19) 0.20733(15) 0.13050(11) 0.0320(4) Uani d . 1 . .
    C C15 0.7210(2) 0.30996(15) 0.17389(12) 0.0336(4) Uani d . 1 . .
    H H15 0.7772 0.3691 0.1451 0.040 Uiso calc R 1 . .
    C C16 0.64315(19) 0.32438(13) 0.26103(11) 0.0293(3) Uani d . 1 . .
    H H16 0.6468 0.3940 0.2927 0.035 Uiso calc R 1 . .
    C C21 0.19553(18) 0.28671(13) 0.64695(11) 0.0256(3) Uani d . 1 . .
    C C22 0.1432(2) 0.39581(14) 0.65039(12) 0.0334(4) Uani d . 1 . .
    H H22 0.1616 0.4443 0.5975 0.040 Uiso calc R 1 . .
    C C23 0.0637(2) 0.43343(15) 0.73191(14) 0.0399(4) Uani d . 1 . .
    H H23 0.0287 0.5078 0.7343 0.048 Uiso calc R 1 . .
    C C24 0.0352(2) 0.36344(16) 0.80929(13) 0.0389(4) Uani d . 1 . .
    H H24 -0.0188 0.3895 0.8646 0.047 Uiso calc R 1 . .
    C C25 0.0864(2) 0.25506(16) 0.80501(12) 0.0360(4) Uani d . 1 . .
    H H25 0.0666 0.2068 0.8578 0.043 Uiso calc R 1 . .
    C C26 0.16682(19) 0.21546(14) 0.72428(11) 0.0313(4) Uani d . 1 . .
    H H26 0.2014 0.1409 0.7222 0.038 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0497(3) 0.0230(2) 0.0519(3) 0.00346(18) 0.0294(2) 0.00788(19)
    O1 0.0479(7) 0.0208(6) 0.0321(6) -0.0008(5) 0.0179(5) -0.0017(5)
    N1 0.0356(7) 0.0207(7) 0.0276(7) 0.0039(5) 0.0134(5) 0.0024(5)
    N2 0.0341(7) 0.0226(7) 0.0261(7) -0.0001(5) 0.0120(5) 0.0010(6)
    N3 0.0408(8) 0.0710(12) 0.0259(7) 0.0174(8) 0.0050(6) -0.0059(8)
    O3 0.0937(13) 0.0830(12) 0.0467(9) 0.0268(10) 0.0450(9) 0.0214(9)
    O4 0.0732(11) 0.0910(13) 0.0504(9) 0.0029(9) 0.0198(8) -0.0404(9)
    C1 0.0283(8) 0.0229(8) 0.0240(7) -0.0011(6) 0.0054(6) 0.0000(6)
    C2 0.0273(7) 0.0254(8) 0.0271(7) 0.0016(6) 0.0074(6) 0.0026(6)
    C11 0.0273(7) 0.0243(8) 0.0224(7) 0.0023(6) 0.0038(6) 0.0006(6)
    C12 0.0370(8) 0.0261(8) 0.0260(7) 0.0001(6) 0.0023(6) -0.0015(6)
    C13 0.0434(9) 0.0336(9) 0.0269(8) 0.0076(7) -0.0003(7) -0.0088(7)
    C14 0.0324(8) 0.0455(10) 0.0184(7) 0.0116(7) 0.0045(6) -0.0012(7)
    C15 0.0352(8) 0.0380(9) 0.0284(8) 0.0009(7) 0.0104(7) 0.0053(7)
    C16 0.0368(8) 0.0249(8) 0.0270(8) -0.0002(6) 0.0092(6) -0.0012(6)
    C21 0.0248(7) 0.0281(8) 0.0244(7) -0.0015(6) 0.0064(6) -0.0023(6)
    C22 0.0382(9) 0.0284(8) 0.0343(8) -0.0008(7) 0.0093(7) -0.0017(7)
    C23 0.0400(9) 0.0352(9) 0.0456(10) 0.0029(7) 0.0125(8) -0.0114(8)
    C24 0.0334(9) 0.0512(11) 0.0331(9) -0.0017(8) 0.0119(7) -0.0128(8)
    C25 0.0345(9) 0.0482(10) 0.0261(8) -0.0041(7) 0.0097(7) 0.0007(7)
    C26 0.0321(8) 0.0344(9) 0.0283(8) 0.0002(7) 0.0092(6) 0.0019(7)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C2 . 1.6661(15) ?
    O1 C1 . 1.2345(18) ?
    N1 C1 . 1.373(2) ?
    N1 C2 . 1.4111(18) ?
    N1 H1 . 0.85(2) ?
    N2 C2 . 1.3373(19) ?
    N2 C21 . 1.4276(19) ?
    N2 H2 . 0.86(2) ?
    N3 O3 . 1.215(2) ?
    N3 O4 . 1.224(2) ?
    N3 C14 . 1.489(2) ?
    C1 C11 . 1.501(2) ?
    C11 C12 . 1.397(2) ?
    C11 C16 . 1.399(2) ?
    C12 C13 . 1.390(2) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.383(3) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.380(3) ?
    C15 C16 . 1.391(2) ?
    C15 H15 . 0.9500 ?
    C16 H16 . 0.9500 ?
    C21 C26 . 1.395(2) ?
    C21 C22 . 1.395(2) ?
    C22 C23 . 1.397(2) ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.386(3) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.385(3) ?
    C24 H24 . 0.9500 ?
    C25 C26 . 1.399(2) ?
    C25 H25 . 0.9500 ?
    C26 H26 . 0.9500 ?
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
    C1 N1 C2 . . 129.32(13) ?
    C1 N1 H1 . . 119.7(13) ?
    C2 N1 H1 . . 111.0(13) ?
    C2 N2 C21 . . 131.25(14) ?
    C2 N2 H2 . . 114.0(14) ?
    C21 N2 H2 . . 114.8(14) ?
    O3 N3 O4 . . 124.27(16) ?
    O3 N3 C14 . . 118.18(17) ?
    O4 N3 C14 . . 117.55(18) ?
    O1 C1 N1 . . 122.69(13) ?
    O1 C1 C11 . . 121.20(13) ?
    N1 C1 C11 . . 116.11(13) ?
    N2 C2 N1 . . 114.45(13) ?
    N2 C2 S1 . . 128.43(11) ?
    N1 C2 S1 . . 117.09(11) ?
    C12 C11 C16 . . 119.68(14) ?
    C12 C11 C1 . . 122.65(13) ?
    C16 C11 C1 . . 117.59(13) ?
    C13 C12 C11 . . 120.42(15) ?
    C13 C12 H12 . . 119.8 ?
    C11 C12 H12 . . 119.8 ?
    C14 C13 C12 . . 118.12(15) ?
    C14 C13 H13 . . 120.9 ?
    C12 C13 H13 . . 120.9 ?
    C15 C14 C13 . . 123.22(14) ?
    C15 C14 N3 . . 118.07(16) ?
    C13 C14 N3 . . 118.70(16) ?
    C14 C15 C16 . . 118.10(15) ?
    C14 C15 H15 . . 120.9 ?
    C16 C15 H15 . . 120.9 ?
    C15 C16 C11 . . 120.43(15) ?
    C15 C16 H16 . . 119.8 ?
    C11 C16 H16 . . 119.8 ?
    C26 C21 C22 . . 119.99(14) ?
    C26 C21 N2 . . 124.90(14) ?
    C22 C21 N2 . . 114.98(14) ?
    C21 C22 C23 . . 119.72(16) ?
    C21 C22 H22 . . 120.1 ?
    C23 C22 H22 . . 120.1 ?
    C24 C23 C22 . . 120.73(17) ?
    C24 C23 H23 . . 119.6 ?
    C22 C23 H23 . . 119.6 ?
    C25 C24 C23 . . 119.20(15) ?
    C25 C24 H24 . . 120.4 ?
    C23 C24 H24 . . 120.4 ?
    C24 C25 C26 . . 121.15(16) ?
    C24 C25 H25 . . 119.4 ?
    C26 C25 H25 . . 119.4 ?
    C21 C26 C25 . . 119.20(16) ?
    C21 C26 H26 . . 120.4 ?
    C25 C26 H26 . . 120.4 ?
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
    C2 N1 C1 O1 . . . . 9.0(3) ?
    C2 N1 C1 C11 . . . . -170.27(15) ?
    C21 N2 C2 N1 . . . . -175.45(15) ?
    C21 N2 C2 S1 . . . . 6.5(3) ?
    C1 N1 C2 N2 . . . . -8.4(2) ?
    C1 N1 C2 S1 . . . . 169.96(13) ?
    O1 C1 C11 C12 . . . . -157.92(16) ?
    N1 C1 C11 C12 . . . . 21.4(2) ?
    O1 C1 C11 C16 . . . . 19.0(2) ?
    N1 C1 C11 C16 . . . . -161.71(14) ?
    C16 C11 C12 C13 . . . . 1.3(2) ?
    C1 C11 C12 C13 . . . . 178.13(15) ?
    C11 C12 C13 C14 . . . . -0.9(2) ?
    C12 C13 C14 C15 . . . . -0.3(3) ?
    C12 C13 C14 N3 . . . . 179.65(15) ?
    O3 N3 C14 C15 . . . . -6.6(2) ?
    O4 N3 C14 C15 . . . . 172.86(17) ?
    O3 N3 C14 C13 . . . . 173.47(17) ?
    O4 N3 C14 C13 . . . . -7.1(2) ?
    C13 C14 C15 C16 . . . . 1.0(3) ?
    N3 C14 C15 C16 . . . . -178.89(14) ?
    C14 C15 C16 C11 . . . . -0.6(2) ?
    C12 C11 C16 C15 . . . . -0.5(2) ?
    C1 C11 C16 C15 . . . . -177.50(15) ?
    C2 N2 C21 C26 . . . . 15.9(3) ?
    C2 N2 C21 C22 . . . . -168.24(16) ?
    C26 C21 C22 C23 . . . . 0.7(3) ?
    N2 C21 C22 C23 . . . . -175.42(15) ?
    C21 C22 C23 C24 . . . . -0.4(3) ?
    C22 C23 C24 C25 . . . . -0.1(3) ?
    C23 C24 C25 C26 . . . . 0.3(3) ?
    C22 C21 C26 C25 . . . . -0.5(2) ?
    N2 C21 C26 C25 . . . . 175.20(15) ?
    C24 C25 C26 C21 . . . . 0.0(3) ?
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
    N1 H1 S1 3_656 0.85(2) 2.68(2) 3.4386(14) 148.6(17)
    N2 H2 O1 . 0.86(2) 1.93(2) 2.6673(16) 143(2)
data_global
_journal_date_recd_electronic     2007-07-13
_journal_date_accepted     2007-07-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      8
_journal_page_first     o3553
_journal_page_last     o3553
_journal_paper_category     QO
_journal_coeditor_code     AT2340
_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-(4-Nitrobenzoyl)-3-phenylthiourea
;
loop_
    _publ_author_name
    _publ_author_address
    'Saeed, Aamer'
;
Department of Chemistry
Quaid-i-Azam University, Islamabad
Pakistan
;
    'Bolte, Michael'
;     Institut für Anorganische Chemie
      J. W. Goethe-Universität Frankfurt
      Max-von-Laue-Strasse 7
      60438 Frankfurt/Main
      Germany
;
