#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220460.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_2220460
loop_
_publ_author_name
'Li, Zhu-Bo'
'Li, Jing'
'Dong, Wen-Liang'
'Zuo, Hua'
'He, Xiao-Yan'
_publ_section_title
;
 N-Cyclohexyl-2-(2,3-dichlorophenylsulfanyl)acetamide
;
_journal_coeditor_code           CS2098
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o32
_journal_paper_doi               10.1107/S1600536808040464
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H17 Cl2 N O S'
_chemical_formula_moiety         'C14 H17 Cl2 N O S'
_chemical_formula_sum            'C14 H17 Cl2 N O S'
_chemical_formula_weight         318.25
_chemical_name_systematic
;
N-Cyclohexyl-2-(2,3-dichlorophenylsulfanyl)acetamide
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.849(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.427(2)
_cell_length_b                   12.877(2)
_cell_length_c                   9.1807(16)
_cell_measurement_reflns_used    1963
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.31
_cell_measurement_theta_min      2.79
_cell_volume                     1534.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7968
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.551
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.268
_refine_ls_extinction_coef       0.0083(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0364P)²+0.4415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                1972
_reflns_number_total             2712
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cs2098.cif
_cod_data_source_block           I
_cod_original_cell_volume        1534.3(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220460
_cod_database_fobs_code          2220460
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 0.85908(5) 0.72227(5) 0.05020(7) 0.0493(2) Uani d . 1 . .
Cl Cl1 1.06216(5) 0.73736(6) -0.03167(9) 0.0719(3) Uani d . 1 . .
Cl Cl2 1.24245(6) 0.58238(7) 0.09765(11) 0.0941(3) Uani d . 1 . .
O O1 0.66239(12) 0.81810(13) -0.02975(18) 0.0506(4) Uani d . 1 . .
C C1 1.04846(17) 0.64033(18) 0.0911(3) 0.0455(6) Uani d . 1 . .
C C2 1.12759(19) 0.5724(2) 0.1488(3) 0.0549(7) Uani d . 1 . .
C C3 1.1172(2) 0.4955(2) 0.2479(3) 0.0647(8) Uani d . 1 . .
H H3 1.1712 0.4502 0.2875 0.078 Uiso calc R 1 . .
C C4 1.0261(2) 0.4870(2) 0.2872(3) 0.0639(7) Uani d . 1 . .
H H4 1.0184 0.4352 0.3541 0.077 Uiso calc R 1 . .
C C5 0.94551(19) 0.55371(19) 0.2295(3) 0.0528(6) Uani d . 1 . .
H H5 0.8838 0.5460 0.2567 0.063 Uiso calc R 1 . .
C C6 0.95562(17) 0.63200(17) 0.1317(3) 0.0409(5) Uani d . 1 . .
C C7 0.75922(16) 0.69227(18) 0.1412(3) 0.0436(6) Uani d . 1 . .
H H7A 0.7322 0.6232 0.1129 0.052 Uiso calc R 1 . .
H H7B 0.7862 0.6945 0.2498 0.052 Uiso calc R 1 . .
C C8 0.67521(16) 0.77252(17) 0.0911(3) 0.0395(5) Uani d . 1 . .
N N1 0.61760(14) 0.78834(15) 0.1866(2) 0.0483(5) Uani d . 1 . .
H H1 0.6331 0.7557 0.2711 0.058 Uiso calc R 1 . .
C C9 0.52927(17) 0.85822(19) 0.1558(3) 0.0461(6) Uani d . 1 . .
H H9 0.5418 0.9135 0.0893 0.055 Uiso calc R 1 . .
C C10 0.5189(2) 0.9077(2) 0.2997(3) 0.0596(7) Uani d . 1 . .
H H10A 0.5807 0.9472 0.3443 0.072 Uiso calc R 1 . .
H H10B 0.5121 0.8539 0.3704 0.072 Uiso calc R 1 . .
C C11 0.4258(3) 0.9791(3) 0.2719(4) 0.0849(10) Uani d . 1 . .
H H11A 0.4185 1.0055 0.3676 0.102 Uiso calc R 1 . .
H H11B 0.4368 1.0379 0.2118 0.102 Uiso calc R 1 . .
C C12 0.3288(3) 0.9245(3) 0.1922(4) 0.0917(11) Uani d . 1 . .
H H12A 0.2721 0.9736 0.1706 0.110 Uiso calc R 1 . .
H H12B 0.3133 0.8707 0.2571 0.110 Uiso calc R 1 . .
C C13 0.3393(2) 0.8767(3) 0.0481(4) 0.0904(11) Uani d . 1 . .
H H13A 0.3477 0.9311 -0.0210 0.108 Uiso calc R 1 . .
H H13B 0.2772 0.8383 0.0015 0.108 Uiso calc R 1 . .
C C14 0.4319(2) 0.8039(3) 0.0773(4) 0.0812(10) Uani d . 1 . .
H H14A 0.4203 0.7460 0.1386 0.097 Uiso calc R 1 . .
H H14B 0.4389 0.7763 -0.0178 0.097 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 0.0033 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 S1 C7 . . 102.52(11) ?
C2 C1 C6 . . 120.3(2) ?
C2 C1 Cl1 . . 120.80(19) ?
C6 C1 Cl1 . . 118.90(18) ?
C1 C2 C3 . . 120.9(2) ?
C1 C2 Cl2 . . 120.3(2) ?
C3 C2 Cl2 . . 118.8(2) ?
C4 C3 C2 . . 118.9(2) ?
C4 C3 H3 . . 120.6 ?
C2 C3 H3 . . 120.6 ?
C3 C4 C5 . . 121.1(3) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C4 C5 C6 . . 120.5(2) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C5 C6 C1 . . 118.3(2) ?
C5 C6 S1 . . 125.10(18) ?
C1 C6 S1 . . 116.58(17) ?
C8 C7 S1 . . 107.41(15) ?
C8 C7 H7A . . 110.2 ?
S1 C7 H7A . . 110.2 ?
C8 C7 H7B . . 110.2 ?
S1 C7 H7B . . 110.2 ?
H7A C7 H7B . . 108.5 ?
O1 C8 N1 . . 123.6(2) ?
O1 C8 C7 . . 121.53(19) ?
N1 C8 C7 . . 114.8(2) ?
C8 N1 C9 . . 123.41(19) ?
C8 N1 H1 . . 118.3 ?
C9 N1 H1 . . 118.3 ?
N1 C9 C14 . . 111.9(2) ?
N1 C9 C10 . . 110.20(19) ?
C14 C9 C10 . . 110.7(2) ?
N1 C9 H9 . . 108.0 ?
C14 C9 H9 . . 108.0 ?
C10 C9 H9 . . 108.0 ?
C9 C10 C11 . . 111.5(2) ?
C9 C10 H10A . . 109.3 ?
C11 C10 H10A . . 109.3 ?
C9 C10 H10B . . 109.3 ?
C11 C10 H10B . . 109.3 ?
H10A C10 H10B . . 108.0 ?
C12 C11 C10 . . 111.9(3) ?
C12 C11 H11A . . 109.2 ?
C10 C11 H11A . . 109.2 ?
C12 C11 H11B . . 109.2 ?
C10 C11 H11B . . 109.2 ?
H11A C11 H11B . . 107.9 ?
C11 C12 C13 . . 110.9(3) ?
C11 C12 H12A . . 109.4 ?
C13 C12 H12A . . 109.4 ?
C11 C12 H12B . . 109.4 ?
C13 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 110.7(3) ?
C12 C13 H13A . . 109.5 ?
C14 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
C14 C13 H13B . . 109.5 ?
H13A C13 H13B . . 108.1 ?
C9 C14 C13 . . 111.7(2) ?
C9 C14 H14A . . 109.3 ?
C13 C14 H14A . . 109.3 ?
C9 C14 H14B . . 109.3 ?
C13 C14 H14B . . 109.3 ?
H14A C14 H14B . . 107.9 ?
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 C6 . 1.759(2) ?
S1 C7 . 1.794(2) ?
Cl1 C1 . 1.724(2) ?
Cl2 C2 . 1.728(3) ?
O1 C8 . 1.228(2) ?
C1 C2 . 1.373(3) ?
C1 C6 . 1.394(3) ?
C2 C3 . 1.376(4) ?
C3 C4 . 1.365(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.377(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(3) ?
C5 H5 . 0.9300 ?
C7 C8 . 1.512(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 N1 . 1.325(3) ?
N1 C9 . 1.457(3) ?
N1 H1 . 0.8600 ?
C9 C14 . 1.495(4) ?
C9 C10 . 1.505(3) ?
C9 H9 . 0.9800 ?
C10 C11 . 1.520(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.496(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.499(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.524(4) ?
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
N H0A O2 4_576 0.86 2.01 2.867(2) 177
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
S1 C7 C8 O1 . . . . 25.9(3) ?
S1 C7 C8 N1 . . . . -154.55(17) ?
O1 C8 N1 C9 . . . . 3.0(4) ?
C7 C8 N1 C9 . . . . -176.6(2) ?
C8 N1 C9 C14 . . . . 89.3(3) ?
C8 N1 C9 C10 . . . . -147.0(2) ?
N1 C9 C10 C11 . . . . -178.6(2) ?
C14 C9 C10 C11 . . . . -54.3(3) ?
C9 C10 C11 C12 . . . . 54.7(4) ?
C10 C11 C12 C13 . . . . -55.3(4) ?
C11 C12 C13 C14 . . . . 55.8(4) ?
N1 C9 C14 C13 . . . . 178.9(3) ?
C10 C9 C14 C13 . . . . 55.5(3) ?
C12 C13 C14 C9 . . . . -56.5(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741318
