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#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/36/2223642.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_2223642
loop_
_publ_author_name
'Haider, Zeeshan'
'Khan, Islam Ullah'
'Arshad, Muhammad Nadeem'
'Shafiq, Muhammad'
'Niu, Caoyuan'
_publ_section_title
;
 N-Cyclohexyl-N-methylbenzenesulfonamide
;
_journal_coeditor_code           BT5092
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2892
_journal_paper_doi               10.1107/S1600536809041762
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H19 N O2 S'
_chemical_formula_moiety         'C13 H19 N O2 S'
_chemical_formula_sum            'C13 H19 N O2 S'
_chemical_formula_weight         253.35
_chemical_name_systematic
;
N-Cyclohexyl-N-methylbenzenesulfonamide
;
_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                 109.103(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2729(5)
_cell_length_b                   12.1182(7)
_cell_length_c                   12.5801(7)
_cell_measurement_reflns_used    3617
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.32
_cell_volume                     1335.79(13)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics
;
'SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD detector'
_diffrn_measurement_method       'phi and omega 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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12741
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_correction_T_min  0.9376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0375
_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)+(0.0559P)²+0.2086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                1864
_reflns_number_total             2489
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5092.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223642
_cod_database_fobs_code          2223642
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
C C1 0.67239(19) 0.36402(15) 0.21562(15) 0.0443(5) Uani d . 1 . .
C C2 0.6576(2) 0.33212(18) 0.31729(17) 0.0556(5) Uani d . 1 . .
H H2 0.7103 0.2710 0.3556 0.067 Uiso calc R 1 . .
C C3 0.5644(2) 0.3918(2) 0.3605(2) 0.0694(7) Uani d . 1 . .
H H3 0.5552 0.3717 0.4294 0.083 Uiso calc R 1 . .
C C4 0.4849(3) 0.4804(2) 0.3038(2) 0.0738(7) Uani d . 1 . .
H H4 0.4200 0.5192 0.3332 0.089 Uiso calc R 1 . .
C C5 0.5005(3) 0.51236(19) 0.2034(2) 0.0732(7) Uani d . 1 . .
H H5 0.4467 0.5731 0.1652 0.088 Uiso calc R 1 . .
C C6 0.5951(2) 0.45494(17) 0.15921(18) 0.0568(5) Uani d . 1 . .
H H6 0.6070 0.4772 0.0918 0.068 Uiso calc R 1 . .
C C7 1.0474(2) 0.29629(15) 0.33830(14) 0.0424(4) Uani d . 1 . .
H H7 0.9836 0.2401 0.3570 0.051 Uiso calc R 1 . .
C C8 1.0716(2) 0.38752(18) 0.42469(16) 0.0568(5) Uani d . 1 . .
H H8A 0.9739 0.4194 0.4203 0.068 Uiso calc R 1 . .
H H8B 1.1338 0.4452 0.4084 0.068 Uiso calc R 1 . .
C C9 1.1495(2) 0.3434(2) 0.54232(16) 0.0632(6) Uani d . 1 . .
H H9A 1.1678 0.4037 0.5958 0.076 Uiso calc R 1 . .
H H9B 1.0829 0.2907 0.5610 0.076 Uiso calc R 1 . .
C C10 1.2988(2) 0.2885(2) 0.55192(17) 0.0651(6) Uani d . 1 . .
H H10A 1.3416 0.2563 0.6262 0.078 Uiso calc R 1 . .
H H10B 1.3701 0.3434 0.5430 0.078 Uiso calc R 1 . .
C C11 1.2786(3) 0.1995(2) 0.46425(18) 0.0679(7) Uani d . 1 . .
H H11A 1.2203 0.1392 0.4805 0.082 Uiso calc R 1 . .
H H11B 1.3780 0.1710 0.4682 0.082 Uiso calc R 1 . .
C C12 1.1976(2) 0.24159(18) 0.34615(16) 0.0546(5) Uani d . 1 . .
H H12A 1.1787 0.1805 0.2936 0.065 Uiso calc R 1 . .
H H12B 1.2625 0.2943 0.3255 0.065 Uiso calc R 1 . .
C C13 1.0145(3) 0.4353(2) 0.18252(19) 0.0719(7) Uani d . 1 . .
H H13A 0.9857 0.4965 0.2197 0.108 Uiso calc R 1 . .
H H13B 0.9659 0.4421 0.1027 0.108 Uiso calc R 1 . .
H H13C 1.1233 0.4350 0.1996 0.108 Uiso calc R 1 . .
N N1 0.96659(17) 0.33232(13) 0.22141(13) 0.0485(4) Uani d . 1 . .
O O1 0.78750(17) 0.17730(12) 0.18902(14) 0.0710(5) Uani d . 1 . .
O O2 0.75416(18) 0.32058(15) 0.04381(11) 0.0769(5) Uani d . 1 . .
S S1 0.79429(6) 0.29004(4) 0.15969(4) 0.0523(2) Uani 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
C6 C1 C2 . . 120.5(2) ?
C6 C1 S1 . . 119.68(16) ?
C2 C1 S1 . . 119.84(15) ?
C3 C2 C1 . . 119.1(2) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C4 C3 C2 . . 120.8(2) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C3 C4 C5 . . 120.1(2) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C6 C5 C4 . . 120.2(2) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C1 . . 119.4(2) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
N1 C7 C8 . . 113.90(15) ?
N1 C7 C12 . . 110.43(15) ?
C8 C7 C12 . . 110.80(15) ?
N1 C7 H7 . . 107.1 ?
C8 C7 H7 . . 107.1 ?
C12 C7 H7 . . 107.1 ?
C7 C8 C9 . . 110.76(17) ?
C7 C8 H8A . . 109.5 ?
C9 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
C9 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.1 ?
C10 C9 C8 . . 111.50(17) ?
C10 C9 H9A . . 109.3 ?
C8 C9 H9A . . 109.3 ?
C10 C9 H9B . . 109.3 ?
C8 C9 H9B . . 109.3 ?
H9A C9 H9B . . 108.0 ?
C9 C10 C11 . . 111.51(18) ?
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 ?
C10 C11 C12 . . 112.27(18) ?
C10 C11 H11A . . 109.2 ?
C12 C11 H11A . . 109.1 ?
C10 C11 H11B . . 109.1 ?
C12 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.9 ?
C11 C12 C7 . . 111.14(17) ?
C11 C12 H12A . . 109.4 ?
C7 C12 H12A . . 109.4 ?
C11 C12 H12B . . 109.4 ?
C7 C12 H12B . . 109.4 ?
H12A C12 H12B . . 108.0 ?
N1 C13 H13A . . 109.5 ?
N1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C13 N1 C7 . . 118.27(15) ?
C13 N1 S1 . . 118.12(13) ?
C7 N1 S1 . . 118.92(12) ?
O1 S1 O2 . . 119.63(10) ?
O1 S1 N1 . . 107.52(9) ?
O2 S1 N1 . . 107.13(10) ?
O1 S1 C1 . . 107.27(10) ?
O2 S1 C1 . . 106.79(9) ?
N1 S1 C1 . . 108.06(8) ?
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
C1 C6 . 1.378(3) ?
C1 C2 . 1.385(3) ?
C1 S1 . 1.760(2) ?
C2 C3 . 1.369(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.364(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.374(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.372(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.481(2) ?
C7 C8 . 1.515(3) ?
C7 C12 . 1.516(3) ?
C7 H7 . 0.9800 ?
C8 C9 . 1.516(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.505(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.509(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.517(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 N1 . 1.462(3) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
N1 S1 . 1.6144(16) ?
O1 S1 . 1.4218(16) ?
O2 S1 . 1.4302(15) ?
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
C2 H2 O2 4_566 0.93 2.52 3.268(3) 137 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 581999
