##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-07-01
_journal_date_accepted     2010-08-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     o2241
_journal_page_last     o2241
_journal_paper_category     QO
_journal_coeditor_code     DN2588
_publ_contact_author_name     'Yamin, Bohari M.'
_publ_contact_author_address
;
      School of Chemical Sciences and Food Technology
      Univeriti  Kebangsaan Malaysia
      UKM 43500 Bangi Selangor. Malaysia
;
_publ_contact_author_email     'bohari@ukm.my'
_publ_contact_author_fax     '03 89215410'
_publ_contact_author_phone     '03 89213993'
_publ_section_title
;
N-(4-Chlorobenzoyl)-N'-(3-fluorophenyl)thiourea
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Othman, Nur Eliyanti A.' ?
;     School of Chemical Sciences and Food Technology
      Universiti Kebangsaan Malaysia
      UKM 43500 Bangi Selangor
      Malaysia
;
    'Tahir, M. Ibrahim M.' ?
;     Department of Chemistry
      Faculty of Science
      Universiti Putra Malaysia
      43400 UPM Serdang, Selangor
      Malaysia
;
    'Yamin, Bohari M.' ?
;     School of Chemical Sciences and Food Technology
      Universiti Kebangsaan Malaysia
      UKM 43500 Bangi Selangor
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-(4-Chlorobenzoyl)-N'-(3-fluorophenyl)thiourea
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C14 H10 Cl F N2 O S'
_chemical_formula_sum     'C14 H10 Cl F N2 O S'
_chemical_formula_iupac     'C14 H10 Cl F N2 O S'
_chemical_formula_weight     308.75
_chemical_melting_point     459
_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     8.57780(10)
_cell_length_b     11.7584(2)
_cell_length_c     13.4069(2)
_cell_angle_alpha     90.00
_cell_angle_beta     92.448(2)
_cell_angle_gamma     90.00
_cell_volume     1351.00(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     24507
_cell_measurement_theta_min     5.00
_cell_measurement_theta_max     72.71
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.29
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.518
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     632
_exptl_absorpt_coefficient_mu     4.033
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2010)
;
_exptl_absorpt_correction_T_min     0.2376
_exptl_absorpt_correction_T_max     0.4321
_exptl_special_details
;
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm,
CrysAlisPro (Oxford Diffraction, 2010)
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur Eos Gemini
;
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.1952
_diffrn_reflns_number     33403
_diffrn_reflns_av_R_equivalents     0.0267
_diffrn_reflns_av_sigmaI/netI     0.0085
_diffrn_reflns_theta_min     5.00
_diffrn_reflns_theta_max     72.71
_diffrn_reflns_theta_full     72.7
_diffrn_measured_fraction_theta_max     0.99
_diffrn_measured_fraction_theta_full     0.99
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     10
_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     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_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 >
σ(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     2685
_reflns_number_gt     2628
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0329
_refine_ls_R_factor_gt     0.0324
_refine_ls_wR_factor_gt     0.0899
_refine_ls_wR_factor_ref     0.0904
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_restrained_S_all     1.062
_refine_ls_number_reflns     2685
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0565P)²+0.5662P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.31
_refine_diff_density_min     -0.27
_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' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'F' 'F' 0.0727 0.0534
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.3331 0.5567
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.3639 0.7018
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CrysAlis Pro (Oxford Diffraction, 2010)'
_computing_cell_refinement     'CrysAlis Pro (Oxford Diffraction, 2010)'
_computing_data_reduction     'CrysAlis Pro (Oxford Diffraction, 2010)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
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
    Cl Cl1 0.68504(4) 0.20726(4) 0.98436(3) 0.03536(13) Uani d . 1 . .
    S S1 1.21472(5) 0.03202(3) 0.43885(3) 0.03022(13) Uani d . 1 . .
    F F1 1.42690(13) 0.17249(11) 0.12225(8) 0.0484(3) Uani d . 1 . .
    O O1 1.06117(13) 0.36258(8) 0.58155(8) 0.0294(2) Uani d . 1 . .
    N N1 1.06930(14) 0.17096(10) 0.55597(9) 0.0236(3) Uani d . 1 . .
    H H1A 1.0313 0.1078 0.5764 0.028 Uiso calc R 1 . .
    N N2 1.20911(14) 0.26185(10) 0.43716(9) 0.0244(3) Uani d . 1 . .
    H H2A 1.1773 0.3206 0.4686 0.029 Uiso calc R 1 . .
    C C1 0.94098(17) 0.14201(12) 0.75021(11) 0.0247(3) Uani d . 1 . .
    H H1B 0.9950 0.0807 0.7247 0.030 Uiso calc R 1 . .
    C C2 0.86286(18) 0.12932(13) 0.83788(11) 0.0278(3) Uani d . 1 . .
    H H2B 0.8634 0.0600 0.8712 0.033 Uiso calc R 1 . .
    C C3 0.78396(17) 0.22191(13) 0.87489(10) 0.0255(3) Uani d . 1 . .
    C C4 0.78102(18) 0.32590(13) 0.82683(11) 0.0284(3) Uani d . 1 . .
    H H4A 0.7276 0.3871 0.8530 0.034 Uiso calc R 1 . .
    C C5 0.85897(18) 0.33731(12) 0.73923(11) 0.0265(3) Uani d . 1 . .
    H H5A 0.8578 0.4069 0.7062 0.032 Uiso calc R 1 . .
    C C6 0.93944(16) 0.24564(11) 0.69979(10) 0.0216(3) Uani d . 1 . .
    C C7 1.02701(16) 0.26641(12) 0.60795(10) 0.0226(3) Uani d . 1 . .
    C C8 1.16519(16) 0.16253(12) 0.47485(10) 0.0220(3) Uani d . 1 . .
    C C9 1.29923(16) 0.28669(12) 0.35414(11) 0.0245(3) Uani d . 1 . .
    C C10 1.35933(19) 0.39669(14) 0.34964(13) 0.0330(3) Uani d . 1 . .
    H H10A 1.3439 0.4479 0.4012 0.040 Uiso calc R 1 . .
    C C11 1.4424(2) 0.42933(16) 0.26764(15) 0.0414(4) Uani d . 1 . .
    H H11A 1.4825 0.5027 0.2651 0.050 Uiso calc R 1 . .
    C C12 1.46672(19) 0.35550(16) 0.19007(14) 0.0398(4) Uani d . 1 . .
    H H12A 1.5221 0.3776 0.1352 0.048 Uiso calc R 1 . .
    C C13 1.40591(18) 0.24824(16) 0.19719(12) 0.0333(4) Uani d . 1 . .
    C C14 1.32205(17) 0.21067(13) 0.27676(11) 0.0274(3) Uani d . 1 . .
    H H14A 1.2824 0.1371 0.2784 0.033 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
    Cl1 0.0334(2) 0.0521(3) 0.02125(19) -0.00362(16) 0.00978(15) -0.00270(15)
    S1 0.0401(2) 0.01980(19) 0.0323(2) -0.00030(13) 0.01862(16) -0.00299(13)
    F1 0.0517(6) 0.0658(7) 0.0294(5) 0.0014(5) 0.0214(4) 0.0013(5)
    O1 0.0390(6) 0.0187(5) 0.0315(6) -0.0022(4) 0.0119(5) -0.0016(4)
    N1 0.0312(6) 0.0176(5) 0.0228(6) -0.0027(5) 0.0098(5) -0.0013(4)
    N2 0.0294(6) 0.0201(6) 0.0243(6) -0.0004(5) 0.0085(5) -0.0008(4)
    C1 0.0313(7) 0.0213(6) 0.0219(7) 0.0031(5) 0.0034(5) -0.0026(5)
    C2 0.0347(8) 0.0268(7) 0.0220(7) -0.0002(6) 0.0024(6) 0.0018(5)
    C3 0.0235(7) 0.0366(8) 0.0165(6) -0.0032(6) 0.0030(5) -0.0035(5)
    C4 0.0304(7) 0.0287(7) 0.0263(7) 0.0042(6) 0.0051(6) -0.0075(6)
    C5 0.0328(8) 0.0213(7) 0.0256(7) 0.0015(6) 0.0039(6) -0.0029(5)
    C6 0.0237(6) 0.0216(6) 0.0194(6) -0.0008(5) 0.0024(5) -0.0028(5)
    C7 0.0250(7) 0.0205(7) 0.0223(7) 0.0001(5) 0.0028(5) -0.0025(5)
    C8 0.0242(6) 0.0217(6) 0.0202(6) -0.0013(5) 0.0037(5) -0.0009(5)
    C9 0.0206(6) 0.0269(7) 0.0262(7) 0.0007(5) 0.0031(5) 0.0077(5)
    C10 0.0328(8) 0.0265(7) 0.0400(9) -0.0007(6) 0.0041(6) 0.0072(6)
    C11 0.0337(8) 0.0351(9) 0.0558(11) -0.0053(7) 0.0077(8) 0.0205(8)
    C12 0.0295(8) 0.0516(10) 0.0393(9) 0.0025(7) 0.0121(7) 0.0224(8)
    C13 0.0264(7) 0.0474(9) 0.0267(8) 0.0051(7) 0.0072(6) 0.0090(7)
    C14 0.0243(7) 0.0327(8) 0.0258(7) -0.0003(6) 0.0062(6) 0.0048(6)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    Cl1 C3 . 1.7350(14) ?
    S1 C8 . 1.6691(14) ?
    F1 C13 . 1.360(2) ?
    O1 C7 . 1.2243(18) ?
    N1 C7 . 1.3778(18) ?
    N1 C8 . 1.3949(17) ?
    N1 H1A . 0.8600 ?
    N2 C8 . 1.3332(18) ?
    N2 C9 . 1.4125(18) ?
    N2 H2A . 0.8600 ?
    C1 C2 . 1.386(2) ?
    C1 C6 . 1.393(2) ?
    C1 H1B . 0.9300 ?
    C2 C3 . 1.385(2) ?
    C2 H2B . 0.9300 ?
    C3 C4 . 1.382(2) ?
    C4 C5 . 1.383(2) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.396(2) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.4896(19) ?
    C9 C14 . 1.390(2) ?
    C9 C10 . 1.395(2) ?
    C10 C11 . 1.390(2) ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.377(3) ?
    C11 H11A . 0.9300 ?
    C12 C13 . 1.370(3) ?
    C12 H12A . 0.9300 ?
    C13 C14 . 1.384(2) ?
    C14 H14A . 0.9300 ?
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
    C7 N1 C8 . . 128.98(12) ?
    C7 N1 H1A . . 115.5 ?
    C8 N1 H1A . . 115.5 ?
    C8 N2 C9 . . 130.76(13) ?
    C8 N2 H2A . . 114.6 ?
    C9 N2 H2A . . 114.6 ?
    C2 C1 C6 . . 120.71(13) ?
    C2 C1 H1B . . 119.6 ?
    C6 C1 H1B . . 119.6 ?
    C3 C2 C1 . . 118.74(14) ?
    C3 C2 H2B . . 120.6 ?
    C1 C2 H2B . . 120.6 ?
    C2 C3 C4 . . 121.87(13) ?
    C2 C3 Cl1 . . 119.29(12) ?
    C4 C3 Cl1 . . 118.84(11) ?
    C5 C4 C3 . . 118.83(14) ?
    C5 C4 H4A . . 120.6 ?
    C3 C4 H4A . . 120.6 ?
    C4 C5 C6 . . 120.77(14) ?
    C4 C5 H5A . . 119.6 ?
    C6 C5 H5A . . 119.6 ?
    C1 C6 C5 . . 119.09(13) ?
    C1 C6 C7 . . 123.35(12) ?
    C5 C6 C7 . . 117.48(13) ?
    O1 C7 N1 . . 122.32(13) ?
    O1 C7 C6 . . 121.72(12) ?
    N1 C7 C6 . . 115.94(12) ?
    N2 C8 N1 . . 114.77(12) ?
    N2 C8 S1 . . 128.04(11) ?
    N1 C8 S1 . . 117.17(10) ?
    C14 C9 C10 . . 120.01(14) ?
    C14 C9 N2 . . 123.68(13) ?
    C10 C9 N2 . . 116.20(14) ?
    C11 C10 C9 . . 119.56(16) ?
    C11 C10 H10A . . 120.2 ?
    C9 C10 H10A . . 120.2 ?
    C12 C11 C10 . . 121.50(16) ?
    C12 C11 H11A . . 119.2 ?
    C10 C11 H11A . . 119.2 ?
    C13 C12 C11 . . 117.22(15) ?
    C13 C12 H12A . . 121.4 ?
    C11 C12 H12A . . 121.4 ?
    F1 C13 C12 . . 119.25(15) ?
    F1 C13 C14 . . 116.73(16) ?
    C12 C13 C14 . . 124.02(17) ?
    C13 C14 C9 . . 117.68(15) ?
    C13 C14 H14A . . 121.2 ?
    C9 C14 H14A . . 121.2 ?
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(2) ?
    C1 C2 C3 C4 . . . . 0.1(2) ?
    C1 C2 C3 Cl1 . . . . 179.79(11) ?
    C2 C3 C4 C5 . . . . 0.1(2) ?
    Cl1 C3 C4 C5 . . . . -179.56(11) ?
    C3 C4 C5 C6 . . . . 0.0(2) ?
    C2 C1 C6 C5 . . . . 0.5(2) ?
    C2 C1 C6 C7 . . . . 177.04(13) ?
    C4 C5 C6 C1 . . . . -0.3(2) ?
    C4 C5 C6 C7 . . . . -177.01(13) ?
    C8 N1 C7 O1 . . . . 6.6(2) ?
    C8 N1 C7 C6 . . . . -172.23(13) ?
    C1 C6 C7 O1 . . . . -158.63(14) ?
    C5 C6 C7 O1 . . . . 17.9(2) ?
    C1 C6 C7 N1 . . . . 20.2(2) ?
    C5 C6 C7 N1 . . . . -163.19(13) ?
    C9 N2 C8 N1 . . . . -177.20(13) ?
    C9 N2 C8 S1 . . . . 4.6(2) ?
    C7 N1 C8 N2 . . . . -7.1(2) ?
    C7 N1 C8 S1 . . . . 171.32(12) ?
    C8 N2 C9 C14 . . . . 20.2(2) ?
    C8 N2 C9 C10 . . . . -163.45(15) ?
    C14 C9 C10 C11 . . . . -0.3(2) ?
    N2 C9 C10 C11 . . . . -176.72(14) ?
    C9 C10 C11 C12 . . . . 0.2(3) ?
    C10 C11 C12 C13 . . . . -0.2(3) ?
    C11 C12 C13 F1 . . . . 179.93(15) ?
    C11 C12 C13 C14 . . . . 0.3(3) ?
    F1 C13 C14 C9 . . . . 180.00(13) ?
    C12 C13 C14 C9 . . . . -0.3(2) ?
    C10 C9 C14 C13 . . . . 0.3(2) ?
    N2 C9 C14 C13 . . . . 176.49(13) ?
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
    C14 H14A S1 . . 1_555 0.93 2.57 3.1865(15) 124 yes
    N2 H2A O1 . . 1_555 0.86 1.91 2.6402(16) 141 yes
    N1 H1A S1 . . 3_756 0.86 2.68 3.4134(13) 145 yes
    C2 H2B O1 . . 2_746 0.93 2.48 3.3717(18) 160 yes
