#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/43/2224324.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_2224324
loop_
_publ_author_name
'Khan, Islam Ullah'
'Haider, Zeeshan'
'Zia-ur-Rehman, Muhammad'
'Arshad, Muhammad Nadeem'
'Shafiq, Muhammad'
_publ_section_title
;
 N-Cyclohexyl-N-(prop-2-en-1-yl)benzenesulfonamide
;
_journal_coeditor_code           IS2487
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3102
_journal_paper_doi               10.1107/S1600536809048077
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C15 H21 N O2 S'
_chemical_formula_moiety         'C15 H21 N O2 S'
_chemical_formula_sum            'C15 H21 N O2 S'
_chemical_formula_weight         279.39
_chemical_name_systematic
;
N-Cyclohexyl-N-(prop-2-en-1-yl)benzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.188(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4911(5)
_cell_length_b                   11.4176(6)
_cell_length_c                   15.6274(10)
_cell_measurement_reflns_used    3312
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.31
_cell_measurement_theta_min      2.21
_cell_volume                     1511.00(15)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and Mercury (Macrae et al.,  2006)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16559
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.9237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'Light yellow'
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.341
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0516
_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)+(0.0594P)²+0.3938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                2179
_reflns_number_total             3746
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2487.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224324
_cod_database_fobs_code          2224324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.27668(7) 0.31209(5) 0.25071(4) 0.0519(2) Uani d . 1 . .
O O1 0.3713(2) 0.21435(17) 0.27943(11) 0.0744(6) Uani d . 1 . .
O O2 0.3425(2) 0.42730(16) 0.25495(14) 0.0776(6) Uani d . 1 . .
N N1 0.1228(2) 0.31154(15) 0.30554(12) 0.0460(5) Uani d . 1 . .
C C1 0.2123(2) 0.28696(18) 0.14300(14) 0.0438(5) Uani d . 1 . .
C C2 0.1843(3) 0.3808(2) 0.08789(19) 0.0714(8) Uani d . 1 . .
H H2 0.2024 0.4570 0.1073 0.086 Uiso calc R 1 . .
C C3 0.1297(4) 0.3605(3) 0.0047(2) 0.0942(11) Uani d . 1 . .
H H3 0.1097 0.4233 -0.0324 0.113 Uiso calc R 1 . .
C C4 0.1044(4) 0.2497(4) -0.02421(19) 0.0881(10) Uani d . 1 . .
H H4 0.0692 0.2370 -0.0812 0.106 Uiso calc R 1 . .
C C5 0.1303(3) 0.1558(3) 0.03010(18) 0.0744(8) Uani d . 1 . .
H H5 0.1110 0.0801 0.0101 0.089 Uiso calc R 1 . .
C C6 0.1849(3) 0.1740(2) 0.11428(16) 0.0534(6) Uani d . 1 . .
H H6 0.2032 0.1108 0.1513 0.064 Uiso calc R 1 . .
C C7 0.0098(2) 0.41024(18) 0.29605(14) 0.0416(5) Uani d . 1 . .
H H7 0.0635 0.4740 0.2679 0.050 Uiso calc R 1 . .
C C8 -0.0307(3) 0.45575(19) 0.38291(14) 0.0485(6) Uani d . 1 . .
H H8A 0.0654 0.4776 0.4164 0.058 Uiso calc R 1 . .
H H8B -0.0819 0.3943 0.4136 0.058 Uiso calc R 1 . .
C C9 -0.1402(3) 0.5618(2) 0.37271(16) 0.0584(7) Uani d . 1 . .
H H9A -0.1702 0.5861 0.4287 0.070 Uiso calc R 1 . .
H H9B -0.0841 0.6263 0.3482 0.070 Uiso calc R 1 . .
C C10 -0.2872(3) 0.5350(2) 0.31574(16) 0.0573(6) Uani d . 1 . .
H H10A -0.3497 0.4769 0.3433 0.069 Uiso calc R 1 . .
H H10B -0.3503 0.6055 0.3078 0.069 Uiso calc R 1 . .
C C11 -0.2460(3) 0.4895(2) 0.22941(16) 0.0621(7) Uani d . 1 . .
H H11A -0.1928 0.5504 0.1993 0.074 Uiso calc R 1 . .
H H11B -0.3421 0.4689 0.1953 0.074 Uiso calc R 1 . .
C C12 -0.1393(3) 0.3822(2) 0.23980(15) 0.0539(6) Uani d . 1 . .
H H12A -0.1959 0.3190 0.2655 0.065 Uiso calc R 1 . .
H H12B -0.1109 0.3563 0.1838 0.065 Uiso calc R 1 . .
C C13 0.0737(3) 0.20179(19) 0.34549(16) 0.0566(6) Uani d . 1 . .
H H13A 0.1046 0.1358 0.3114 0.068 Uiso calc R 1 . .
H H13B -0.0404 0.2007 0.3464 0.068 Uiso calc R 1 . .
C C14 0.1475(4) 0.1896(2) 0.4359(2) 0.0795(9) Uani d . 1 . .
H H14 0.2546 0.2069 0.4439 0.095 Uiso calc R 1 . .
C C15 0.0842(6) 0.1601(3) 0.4985(3) 0.1242(14) Uani d . 1 . .
H H15A -0.0228 0.1417 0.4943 0.149 Uiso calc R 1 . .
H H15B 0.1420 0.1557 0.5513 0.149 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'
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 S1 O2 . . 119.70(12) ?
O1 S1 N1 . . 106.79(11) ?
O2 S1 N1 . . 107.95(10) ?
O1 S1 C1 . . 107.60(10) ?
O2 S1 C1 . . 106.76(12) ?
N1 S1 C1 . . 107.52(10) ?
C13 N1 C7 . . 119.21(17) ?
C13 N1 S1 . . 119.58(14) ?
C7 N1 S1 . . 119.19(14) ?
C6 C1 C2 . . 120.3(2) ?
C6 C1 S1 . . 119.87(17) ?
C2 C1 S1 . . 119.82(19) ?
C3 C2 C1 . . 119.4(3) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C4 C3 C2 . . 120.7(3) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 120.5(3) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.0(3) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C5 C6 C1 . . 119.2(2) ?
C5 C6 H6 . . 120.4 ?
C1 C6 H6 . . 120.4 ?
N1 C7 C8 . . 111.04(17) ?
N1 C7 C12 . . 113.81(17) ?
C8 C7 C12 . . 110.80(18) ?
N1 C7 H7 . . 106.9 ?
C8 C7 H7 . . 106.9 ?
C12 C7 H7 . . 106.9 ?
C7 C8 C9 . . 110.76(19) ?
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 . . 111.75(18) ?
C10 C9 H9A . . 109.3 ?
C8 C9 H9A . . 109.3 ?
C10 C9 H9B . . 109.3 ?
C8 C9 H9B . . 109.3 ?
H9A C9 H9B . . 107.9 ?
C11 C10 C9 . . 111.2(2) ?
C11 C10 H10A . . 109.4 ?
C9 C10 H10A . . 109.4 ?
C11 C10 H10B . . 109.4 ?
C9 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
C10 C11 C12 . . 110.8(2) ?
C10 C11 H11A . . 109.5 ?
C12 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.1 ?
C7 C12 C11 . . 110.82(19) ?
C7 C12 H12A . . 109.5 ?
C11 C12 H12A . . 109.5 ?
C7 C12 H12B . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 108.1 ?
N1 C13 C14 . . 111.3(2) ?
N1 C13 H13A . . 109.4 ?
C14 C13 H13A . . 109.4 ?
N1 C13 H13B . . 109.4 ?
C14 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
C15 C14 C13 . . 127.5(4) ?
C15 C14 H14 . . 116.2 ?
C13 C14 H14 . . 116.2 ?
C14 C15 H15A . . 120.0 ?
C14 C15 H15B . . 120.0 ?
H15A C15 H15B . . 120.0 ?
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 O1 . 1.4283(18) ?
S1 O2 . 1.4289(17) ?
S1 N1 . 1.6136(19) ?
S1 C1 . 1.755(2) ?
N1 C13 . 1.474(3) ?
N1 C7 . 1.481(2) ?
C1 C6 . 1.380(3) ?
C1 C2 . 1.385(3) ?
C2 C3 . 1.368(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.355(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.375(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.378(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.516(3) ?
C7 C12 . 1.522(3) ?
C7 H7 . 0.9800 ?
C8 C9 . 1.528(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.511(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.510(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.525(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.509(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.198(4) ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9300 ?
C15 H15B . 0.9300 ?
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
O1 S1 N1 C13 . . . . -22.4(2) ?
O2 S1 N1 C13 . . . . -152.36(18) ?
C1 S1 N1 C13 . . . . 92.80(18) ?
O1 S1 N1 C7 . . . . 173.87(15) ?
O2 S1 N1 C7 . . . . 43.96(19) ?
C1 S1 N1 C7 . . . . -70.88(17) ?
O1 S1 C1 C6 . . . . 32.0(2) ?
O2 S1 C1 C6 . . . . 161.62(18) ?
N1 S1 C1 C6 . . . . -82.75(19) ?
O1 S1 C1 C2 . . . . -150.1(2) ?
O2 S1 C1 C2 . . . . -20.4(2) ?
N1 S1 C1 C2 . . . . 95.2(2) ?
C6 C1 C2 C3 . . . . -0.2(4) ?
S1 C1 C2 C3 . . . . -178.1(2) ?
C1 C2 C3 C4 . . . . -0.6(5) ?
C2 C3 C4 C5 . . . . 1.3(5) ?
C3 C4 C5 C6 . . . . -1.1(5) ?
C4 C5 C6 C1 . . . . 0.3(4) ?
C2 C1 C6 C5 . . . . 0.3(4) ?
S1 C1 C6 C5 . . . . 178.25(19) ?
C13 N1 C7 C8 . . . . 64.3(2) ?
S1 N1 C7 C8 . . . . -131.93(17) ?
C13 N1 C7 C12 . . . . -61.5(3) ?
S1 N1 C7 C12 . . . . 102.2(2) ?
N1 C7 C8 C9 . . . . 176.87(18) ?
C12 C7 C8 C9 . . . . -55.6(2) ?
C7 C8 C9 C10 . . . . 55.1(3) ?
C8 C9 C10 C11 . . . . -55.4(3) ?
C9 C10 C11 C12 . . . . 56.1(3) ?
N1 C7 C12 C11 . . . . -177.19(19) ?
C8 C7 C12 C11 . . . . 56.8(3) ?
C10 C11 C12 C7 . . . . -56.9(3) ?
C7 N1 C13 C14 . . . . -104.9(2) ?
S1 N1 C13 C14 . . . . 91.5(2) ?
N1 C13 C14 C15 . . . . 134.8(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743861
