#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/57/2225760.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_2225760
loop_
_publ_author_name
'Saeed, Sohail'
'Rashid, Naghmana'
'Wong, Wing-Tak'
_publ_section_title
;
 N-Cyclohexyl-N'-(4-nitrobenzoyl)thiourea
;
_journal_coeditor_code           BH2277
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1031
_journal_page_last               o1032
_journal_paper_doi               10.1107/S1600536810012249
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H17 N3 O3 S'
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.37
_chemical_melting_point          389
_chemical_name_systematic
;
N-Cyclohexyl-N'-(4-nitrobenzoyl)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                 101.4930(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7865(7)
_cell_length_b                   6.9218(4)
_cell_length_c                   20.6788(13)
_cell_measurement_reflns_used    10042
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      1.93
_cell_volume                     1512.96(16)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'SMART (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω
_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  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10042
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.9433
_exptl_absorpt_correction_T_min  0.9086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.196
_refine_ls_extinction_coef       0.0071(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SAINT (Bruker, 2006)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0570P)²+0.3039P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                3177
_reflns_number_total             3683
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2277.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225760
_cod_database_fobs_code          2225760
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
S S1 1.03975(3) 0.73010(6) 0.436999(18) 0.05209(13) Uani d . 1 . .
O O1 0.47704(13) 0.08216(19) 0.65091(7) 0.0781(4) Uani d . 1 . .
O O2 0.44185(17) 0.3242(2) 0.70892(8) 0.1000(5) Uani d . 1 . .
O O3 0.67743(10) 0.91616(15) 0.49838(6) 0.0595(3) Uani d . 1 . .
N N1 0.48457(12) 0.2530(2) 0.66423(7) 0.0597(3) Uani d . 1 . .
N N2 0.83598(10) 0.70331(17) 0.49038(5) 0.0439(2) Uani d . 1 . .
N N3 0.83313(11) 0.94898(16) 0.41468(6) 0.0474(3) Uani d . 1 . .
C C1 0.55199(11) 0.3817(2) 0.62577(6) 0.0469(3) Uani d . 1 . .
C C2 0.56593(15) 0.5738(2) 0.64356(7) 0.0554(3) Uani d . 1 . .
H H2 0.5347 0.6211 0.6792 0.066 Uiso calc R 1 . .
C C3 0.62757(15) 0.6938(2) 0.60694(7) 0.0543(3) Uani d . 1 . .
H H3 0.6368 0.8244 0.6174 0.065 Uiso calc R 1 . .
C C4 0.67605(11) 0.61980(19) 0.55443(6) 0.0429(3) Uani d . 1 . .
C C5 0.66178(11) 0.42564(19) 0.53834(6) 0.0437(3) Uani d . 1 . .
H H5 0.6951 0.3766 0.5035 0.052 Uiso calc R 1 . .
C C6 0.59808(12) 0.30409(19) 0.57394(7) 0.0461(3) Uani d . 1 . .
H H6 0.5868 0.1740 0.5631 0.055 Uiso calc R 1 . .
C C7 0.72985(13) 0.76095(18) 0.51229(6) 0.0440(3) Uani d . 1 . .
C C8 0.89672(11) 0.80319(18) 0.44630(6) 0.0404(3) Uani d . 1 . .
C C9 0.87497(12) 1.07460(18) 0.36608(6) 0.0450(3) Uani d . 1 . .
H H9 0.9669 1.0915 0.3785 0.054 Uiso calc R 1 . .
C C10 0.81166(18) 1.2697(2) 0.36788(8) 0.0581(4) Uani d . 1 . .
H H10A 0.8380 1.3263 0.4114 0.070 Uiso calc R 1 . .
H H10B 0.7206 1.2526 0.3598 0.070 Uiso calc R 1 . .
C C11 0.84568(19) 1.4059(2) 0.31634(8) 0.0675(4) Uani d . 1 . .
H H11A 0.7997 1.5262 0.3168 0.081 Uiso calc R 1 . .
H H11B 0.9354 1.4348 0.3275 0.081 Uiso calc R 1 . .
C C12 0.81434(18) 1.3191(3) 0.24797(8) 0.0660(4) Uani d . 1 . .
H H12A 0.7234 1.3052 0.2346 0.079 Uiso calc R 1 . .
H H12B 0.8429 1.4054 0.2170 0.079 Uiso calc R 1 . .
C C13 0.87599(18) 1.1253(3) 0.24606(8) 0.0650(4) Uani d . 1 . .
H H13A 0.9671 1.1419 0.2539 0.078 Uiso calc R 1 . .
H H13B 0.8492 1.0695 0.2025 0.078 Uiso calc R 1 . .
C C14 0.84263(16) 0.9873(2) 0.29742(7) 0.0567(4) Uani d . 1 . .
H H14A 0.7529 0.9581 0.2866 0.068 Uiso calc R 1 . .
H H14B 0.8888 0.8673 0.2967 0.068 Uiso calc R 1 . .
H H2N 0.8739(16) 0.605(3) 0.5076(8) 0.056(4) Uiso d . 1 . .
H H3N 0.7671(16) 0.977(2) 0.4261(8) 0.054(4) Uiso d . 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'
S S 0.1246 0.1234 '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
O1 N1 O2 . . 123.31(14) ?
O1 N1 C1 . . 118.89(13) ?
O2 N1 C1 . . 117.78(15) ?
C7 N2 C8 . . 126.77(11) ?
C7 N2 H2N . . 117.8(12) ?
C8 N2 H2N . . 115.1(12) ?
C8 N3 C9 . . 126.38(11) ?
C8 N3 H3N . . 115.9(11) ?
C9 N3 H3N . . 117.4(11) ?
C6 C1 C2 . . 123.12(12) ?
C6 C1 N1 . . 118.42(13) ?
C2 C1 N1 . . 118.46(12) ?
C1 C2 C3 . . 118.19(12) ?
C1 C2 H2 . . 120.9 ?
C3 C2 H2 . . 120.9 ?
C2 C3 C4 . . 120.20(13) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C5 C4 C3 . . 120.17(12) ?
C5 C4 C7 . . 121.95(11) ?
C3 C4 C7 . . 117.52(12) ?
C4 C5 C6 . . 120.26(12) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 118.04(12) ?
C1 C6 H6 . . 121.0 ?
C5 C6 H6 . . 121.0 ?
O3 C7 N2 . . 123.77(12) ?
O3 C7 C4 . . 119.66(11) ?
N2 C7 C4 . . 116.56(11) ?
N3 C8 N2 . . 115.75(11) ?
N3 C8 S1 . . 125.16(10) ?
N2 C8 S1 . . 119.09(9) ?
N3 C9 C10 . . 108.03(11) ?
N3 C9 C14 . . 111.11(11) ?
C10 C9 C14 . . 110.89(12) ?
N3 C9 H9 . . 108.9 ?
C10 C9 H9 . . 108.9 ?
C14 C9 H9 . . 108.9 ?
C9 C10 C11 . . 111.20(13) ?
C9 C10 H10A . . 109.4 ?
C11 C10 H10A . . 109.4 ?
C9 C10 H10B . . 109.4 ?
C11 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
C12 C11 C10 . . 111.65(13) ?
C12 C11 H11A . . 109.3 ?
C10 C11 H11A . . 109.3 ?
C12 C11 H11B . . 109.3 ?
C10 C11 H11B . . 109.3 ?
H11A C11 H11B . . 108.0 ?
C13 C12 C11 . . 111.23(14) ?
C13 C12 H12A . . 109.4 ?
C11 C12 H12A . . 109.4 ?
C13 C12 H12B . . 109.4 ?
C11 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 111.98(13) ?
C12 C13 H13A . . 109.2 ?
C14 C13 H13A . . 109.2 ?
C12 C13 H13B . . 109.2 ?
C14 C13 H13B . . 109.2 ?
H13A C13 H13B . . 107.9 ?
C9 C14 C13 . . 111.10(12) ?
C9 C14 H14A . . 109.4 ?
C13 C14 H14A . . 109.4 ?
C9 C14 H14B . . 109.4 ?
C13 C14 H14B . . 109.4 ?
H14A C14 H14B . . 108.0 ?
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 C8 . 1.6707(13) ?
O1 N1 . 1.2132(19) ?
O2 N1 . 1.2162(19) ?
O3 C7 . 1.2213(15) ?
N1 C1 . 1.4785(17) ?
N2 C7 . 1.3717(16) ?
N2 C8 . 1.4058(16) ?
N2 H2N . 0.835(18) ?
N3 C8 . 1.3182(16) ?
N3 C9 . 1.4665(15) ?
N3 H3N . 0.817(17) ?
C1 C6 . 1.3774(18) ?
C1 C2 . 1.379(2) ?
C2 C3 . 1.380(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.3932(17) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.3857(18) ?
C4 C7 . 1.5008(17) ?
C5 C6 . 1.3869(17) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C9 C10 . 1.5173(19) ?
C9 C14 . 1.518(2) ?
C9 H9 . 0.9800 ?
C10 C11 . 1.521(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.511(2) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.501(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.524(2) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
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
N3 H3N O3 . 0.817(17) 1.981(17) 2.6507(17) 138.8(14) yes
N2 H2N S1 3_766 0.84(2) 2.67(2) 3.4999(12) 171.3(16) yes
C6 H6 O3 1_545 0.93 2.54 3.3041(17) 140 no
C9 H9 S1 . 0.98 2.82 3.1555(13) 101 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 806260
