#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/73/2227372.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227372
loop_
_publ_author_name
'Othman, Nur Eliyanti A.'
'Tahir, M. Ibrahim M.'
'Yamin, Bohari M.'
_publ_section_title
;
 N-(4-Chlorobenzoyl)-N'-(3-fluorophenyl)thiourea
;
_journal_coeditor_code           DN2588
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2241
_journal_paper_doi               10.1107/S1600536810030965
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H10 Cl F N2 O S'
_chemical_formula_moiety         'C14 H10 Cl F N2 O S'
_chemical_formula_sum            'C14 H10 Cl F N2 O S'
_chemical_formula_weight         308.75
_chemical_melting_point          459
_chemical_name_systematic
;
N-(4-Chlorobenzoyl)-N'-(3-fluorophenyl)thiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.448(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.57780(10)
_cell_length_b                   11.7584(2)
_cell_length_c                   13.4069(2)
_cell_measurement_reflns_used    24507
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.71
_cell_measurement_theta_min      5.00
_cell_volume                     1351.00(3)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis Pro (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON
(Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1952
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur Eos Gemini
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0085
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33403
_diffrn_reflns_theta_full        72.7
_diffrn_reflns_theta_max         72.71
_diffrn_reflns_theta_min         5.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.033
_exptl_absorpt_correction_T_max  0.4321
_exptl_absorpt_correction_T_min  0.2376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis Pro; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0324
_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)+(0.0565P)²+0.5662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                2628
_reflns_number_total             2685
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2588.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227372
_cod_database_fobs_code          2227372
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'
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_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'
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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21305870
