#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/42/2234212.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2234212
loop_
_publ_author_name
'Yusof, Mohd Sukeri Mohd'
'Embong, Nur Farhana'
'Arshad, Suhana'
'Razak, Ibrahim Abdul'
_publ_section_title
;
 N-(4-Chlorobutanoyl)-N'-[2-(trifluoromethyl)phenyl]thiourea
;
_journal_coeditor_code           HB6655
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1029
_journal_paper_doi               10.1107/S1600536812008859
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H12 Cl F3 N2 O S'
_chemical_formula_moiety         'C12 H12 Cl F3 N2 O S'
_chemical_formula_sum            'C12 H12 Cl F3 N2 O S'
_chemical_formula_weight         324.75
_chemical_name_systematic
;
N-(4-Chlorobutanoyl)-N'-[2-(trifluoromethyl)phenyl]thiourea
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.6870(10)
_cell_angle_beta                 103.4190(10)
_cell_angle_gamma                95.6530(10)
_cell_formula_units_Z            2
_cell_length_a                   7.86220(10)
_cell_length_b                   8.90730(10)
_cell_length_c                   11.03410(10)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      32.58
_cell_measurement_theta_min      2.50
_cell_volume                     672.175(15)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18148
_diffrn_reflns_theta_full        32.64
_diffrn_reflns_theta_max         32.64
_diffrn_reflns_theta_min         2.11
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.471
_exptl_absorpt_correction_T_max  0.9319
_exptl_absorpt_correction_T_min  0.8294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.315
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         4884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0295
_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)+(0.0365P)²+0.3295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                4304
_reflns_number_total             4884
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6655.cif
_cod_data_source_block           I
_cod_database_code               2234212
_cod_database_fobs_code          2234212
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
Cl Cl1 1.66943(3) 0.08190(3) 0.87826(3) 0.01972(6) Uani d . 1 1
S S1 0.77778(4) 0.12238(3) 0.48626(3) 0.01851(6) Uani d . 1 1
F F1 0.97525(9) 0.59829(9) 0.65758(8) 0.02506(15) Uani d . 1 1
F F2 0.86578(9) 0.81937(8) 0.70633(8) 0.02360(14) Uani d . 1 1
F F3 0.97036(10) 0.74396(10) 0.86623(7) 0.02883(16) Uani d . 1 1
O O1 1.11812(11) 0.39045(10) 0.93786(8) 0.02277(17) Uani d . 1 1
N N1 0.83210(12) 0.36357(10) 0.74177(9) 0.01434(15) Uani d . 1 1
N N2 1.02233(11) 0.17737(10) 0.71774(9) 0.01377(15) Uani d . 1 1
C C1 0.69392(13) 0.58116(12) 0.69974(9) 0.01248(16) Uani d . 1 1
C C2 0.54109(13) 0.64135(12) 0.66718(10) 0.01409(16) Uani d . 1 1
H H2A 0.5523 0.7491 0.6683 0.017 Uiso calc R 1 1
C C3 0.37240(13) 0.54429(13) 0.63303(10) 0.01548(17) Uani d . 1 1
H H3A 0.2685 0.5864 0.6123 0.019 Uiso calc R 1 1
C C4 0.35583(14) 0.38496(13) 0.62916(10) 0.01655(18) Uani d . 1 1
H H4A 0.2404 0.3175 0.6038 0.020 Uiso calc R 1 1
C C5 0.50789(14) 0.32467(12) 0.66239(10) 0.01537(17) Uani d . 1 1
H H5A 0.4962 0.2162 0.6598 0.018 Uiso calc R 1 1
C C6 0.67708(13) 0.42288(12) 0.69935(9) 0.01262(16) Uani d . 1 1
C C7 0.87834(13) 0.22901(12) 0.65719(10) 0.01306(16) Uani d . 1 1
C C8 1.13277(14) 0.25600(12) 0.85287(10) 0.01538(17) Uani d . 1 1
C C9 1.27517(14) 0.16553(12) 0.88836(10) 0.01620(17) Uani d . 1 1
H H9A 1.2920 0.0827 0.8021 0.019 Uiso calc R 1 1
H H9B 1.2370 0.1043 0.9385 0.019 Uiso calc R 1 1
C C10 1.45172(14) 0.29236(12) 0.97903(10) 0.01529(17) Uani d . 1 1
H H10A 1.4875 0.3522 0.9272 0.018 Uiso calc R 1 1
H H10B 1.4310 0.3765 1.0628 0.018 Uiso calc R 1 1
C C11 1.60482(14) 0.21825(13) 1.02413(10) 0.01720(18) Uani d . 1 1
H H11A 1.5689 0.1538 1.0726 0.021 Uiso calc R 1 1
H H11B 1.7087 0.3100 1.0902 0.021 Uiso calc R 1 1
C C12 0.87515(13) 0.68537(12) 0.73243(11) 0.01615(17) Uani d . 1 1
H H1N2 1.050(2) 0.0918(19) 0.6625(16) 0.021(4) Uiso d . 1 1
H H1N1 0.895(2) 0.413(2) 0.8270(17) 0.026(4) Uiso d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 N1 C6 123.49(8)
C7 N1 H1N1 118.1(11)
C6 N1 H1N1 118.3(11)
C8 N2 C7 127.83(8)
C8 N2 H1N2 116.8(10)
C7 N2 H1N2 115.1(10)
C2 C1 C6 119.79(9)
C2 C1 C12 119.61(9)
C6 C1 C12 120.59(8)
C3 C2 C1 120.22(9)
C3 C2 H2A 119.9
C1 C2 H2A 119.9
C2 C3 C4 119.88(9)
C2 C3 H3A 120.1
C4 C3 H3A 120.1
C5 C4 C3 120.14(9)
C5 C4 H4A 119.9
C3 C4 H4A 119.9
C4 C5 C6 120.12(9)
C4 C5 H5A 119.9
C6 C5 H5A 119.9
C5 C6 C1 119.81(9)
C5 C6 N1 119.42(8)
C1 C6 N1 120.72(9)
N1 C7 N2 116.42(8)
N1 C7 S1 124.76(7)
N2 C7 S1 118.81(7)
O1 C8 N2 122.61(9)
O1 C8 C9 122.16(9)
N2 C8 C9 115.22(8)
C8 C9 C10 109.74(8)
C8 C9 H9A 109.7
C10 C9 H9A 109.7
C8 C9 H9B 109.7
C10 C9 H9B 109.7
H9A C9 H9B 108.2
C11 C10 C9 115.10(8)
C11 C10 H10A 108.5
C9 C10 H10A 108.5
C11 C10 H10B 108.5
C9 C10 H10B 108.5
H10A C10 H10B 107.5
C10 C11 Cl1 111.48(7)
C10 C11 H11A 109.3
Cl1 C11 H11A 109.3
C10 C11 H11B 109.3
Cl1 C11 H11B 109.3
H11A C11 H11B 108.0
F2 C12 F3 106.59(8)
F2 C12 F1 106.08(8)
F3 C12 F1 106.43(8)
F2 C12 C1 112.63(8)
F3 C12 C1 112.29(8)
F1 C12 C1 112.35(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C11 1.8038(10)
S1 C7 1.6748(10)
F1 C12 1.3455(12)
F2 C12 1.3404(12)
F3 C12 1.3430(12)
O1 C8 1.2255(12)
N1 C7 1.3358(12)
N1 C6 1.4298(12)
N1 H1N1 0.856(17)
N2 C8 1.3813(13)
N2 C7 1.3921(12)
N2 H1N2 0.849(15)
C1 C2 1.3935(13)
C1 C6 1.4011(13)
C1 C12 1.5013(14)
C2 C3 1.3888(14)
C2 H2A 0.9500
C3 C4 1.3947(14)
C3 H3A 0.9500
C4 C5 1.3904(14)
C4 H4A 0.9500
C5 C6 1.3905(14)
C5 H5A 0.9500
C8 C9 1.5112(14)
C9 C10 1.5305(14)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.5082(14)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9900
C11 H11B 0.9900
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
_geom_hbond_publ_flag
N1 H1N1 O1 . 0.855(16) 1.971(17) 2.6486(12) 135.4(16) yes
N1 H1N1 O1 2_767 0.855(16) 2.514(17) 3.2273(12) 141.6(14) yes
N2 H1N2 S1 2_756 0.849(17) 2.682(17) 3.5079(10) 164.7(14) yes
C2 H2A Cl1 1_465 0.95 2.82 3.5535(11) 135 yes
C3 H3A F1 1_455 0.95 2.47 3.2617(13) 140 yes
C9 H9A S1 2_756 0.99 2.84 3.7829(10) 159 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
C6 C1 C2 C3 -0.66(14)
C12 C1 C2 C3 178.23(9)
C1 C2 C3 C4 -1.03(14)
C2 C3 C4 C5 1.43(14)
C3 C4 C5 C6 -0.13(15)
C4 C5 C6 C1 -1.56(14)
C4 C5 C6 N1 176.03(9)
C2 C1 C6 C5 1.95(14)
C12 C1 C6 C5 -176.93(9)
C2 C1 C6 N1 -175.61(8)
C12 C1 C6 N1 5.52(13)
C7 N1 C6 C5 66.17(13)
C7 N1 C6 C1 -116.27(11)
C6 N1 C7 N2 -173.57(9)
C6 N1 C7 S1 7.24(14)
C8 N2 C7 N1 -5.61(15)
C8 N2 C7 S1 173.63(8)
C7 N2 C8 O1 -2.41(17)
C7 N2 C8 C9 178.37(9)
O1 C8 C9 C10 -40.56(14)
N2 C8 C9 C10 138.66(9)
C8 C9 C10 C11 178.93(8)
C9 C10 C11 Cl1 65.16(10)
C2 C1 C12 F2 -9.09(13)
C6 C1 C12 F2 169.80(8)
C2 C1 C12 F3 111.26(10)
C6 C1 C12 F3 -69.86(12)
C2 C1 C12 F1 -128.80(9)
C6 C1 C12 F1 50.08(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657598
