#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/69/2226903.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_2226903
loop_
_publ_author_name
'John, Peter'
'Anwar, Faiza'
'Khan, Islam Ullah'
'Sharif, Shahzad'
'Tiekink, Edward R. T.'
_publ_section_title
;
 4-Bromo-N-cyclohexylbenzenesulfonamide
;
_journal_coeditor_code           HB5542
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1989
_journal_paper_doi               10.1107/S1600536810026796
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H16 Br N O2 S'
_chemical_formula_moiety         'C12 H16 Br N O2 S'
_chemical_formula_sum            'C12 H16 Br N O2 S'
_chemical_formula_weight         318.24
_chemical_name_systematic
;
4-Bromo-N-cyclohexylbenzenesulfonamide
;
_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
_cell_angle_beta                 97.214(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2539(5)
_cell_length_b                   6.2575(3)
_cell_length_c                   19.9743(10)
_cell_measurement_reflns_used    2185
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.1
_cell_measurement_theta_min      2.6
_cell_volume                     1395.48(12)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker 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  0.048
_diffrn_reflns_av_sigmaI/netI    0.062
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12505
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.8
_exptl_absorpt_coefficient_mu    3.086
_exptl_absorpt_correction_T_max  0.529
_exptl_absorpt_correction_T_min  0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.52
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         3199
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.01
_refine_ls_R_factor_all          0.122
_refine_ls_R_factor_gt           0.048
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0552P)²+0.4435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.107
_refine_ls_wR_factor_ref         0.132
_reflns_number_gt                1620
_reflns_number_total             3199
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5542.cif
_cod_data_source_block           I
_cod_original_cell_volume        1395.48(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226903
_cod_database_fobs_code          2226903
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
Br Br1 0.03064(5) 1.13493(9) 0.90414(3) 0.1022(3) Uani d . 1 . .
S S1 0.32555(8) 0.51051(14) 0.73331(5) 0.0523(3) Uani d . 1 . .
O O1 0.4205(2) 0.4370(4) 0.78229(16) 0.0763(9) Uani d . 1 . .
O O2 0.2437(2) 0.3587(3) 0.70013(15) 0.0685(8) Uani d . 1 . .
N N1 0.3875(3) 0.6368(4) 0.67782(17) 0.0497(8) Uani d D 1 . .
H H1N 0.450(2) 0.714(5) 0.6936(17) 0.060 Uiso d D 1 . .
C C1 0.2414(3) 0.6900(5) 0.77706(17) 0.0435(8) Uani d . 1 . .
C C2 0.1289(3) 0.6312(6) 0.7906(2) 0.0584(10) Uani d . 1 . .
H H2 0.0958 0.5019 0.7746 0.070 Uiso calc R 1 . .
C C3 0.0658(3) 0.7644(7) 0.8278(2) 0.0660(11) Uani d . 1 . .
H H3 -0.0102 0.7259 0.8372 0.079 Uiso calc R 1 . .
C C4 0.1155(3) 0.9538(6) 0.8508(2) 0.0582(10) Uani d . 1 . .
C C5 0.2265(4) 1.0149(6) 0.8369(2) 0.0597(10) Uani d . 1 . .
H H5 0.2586 1.1454 0.8524 0.072 Uiso calc R 1 . .
C C6 0.2899(3) 0.8824(6) 0.8000(2) 0.0555(10) Uani d . 1 . .
H H6 0.3655 0.9223 0.7904 0.067 Uiso calc R 1 . .
C C7 0.3239(3) 0.7049(5) 0.61271(19) 0.0515(9) Uani d . 1 . .
H H7 0.2584 0.6039 0.6000 0.062 Uiso calc R 1 . .
C C8 0.4105(5) 0.6910(9) 0.5601(3) 0.0944(16) Uani d . 1 . .
H H8A 0.4799 0.7797 0.5739 0.113 Uiso calc R 1 . .
H H8B 0.4376 0.5446 0.5569 0.113 Uiso calc R 1 . .
C C9 0.3511(6) 0.7641(13) 0.4915(3) 0.121(2) Uani d . 1 . .
H H9A 0.4100 0.7639 0.4599 0.146 Uiso calc R 1 . .
H H9B 0.2886 0.6634 0.4751 0.146 Uiso calc R 1 . .
C C10 0.2986(5) 0.9797(11) 0.4935(3) 0.1082(19) Uani d . 1 . .
H H10A 0.2572 1.0147 0.4493 0.130 Uiso calc R 1 . .
H H10B 0.3623 1.0833 0.5043 0.130 Uiso calc R 1 . .
C C11 0.2126(5) 0.9940(9) 0.5448(3) 0.1004(17) Uani d . 1 . .
H H11A 0.1436 0.9042 0.5310 0.121 Uiso calc R 1 . .
H H11B 0.1848 1.1402 0.5474 0.121 Uiso calc R 1 . .
C C12 0.2716(4) 0.9235(7) 0.6137(2) 0.0770(13) Uani d . 1 . .
H H12A 0.3344 1.0241 0.6297 0.092 Uiso calc R 1 . .
H H12B 0.2126 0.9260 0.6452 0.092 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 0.0030 0.0020 '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'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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
O2 S1 O1 . . 119.11(17) ?
O2 S1 N1 . . 108.71(17) ?
O1 S1 N1 . . 106.31(17) ?
O2 S1 C1 . . 107.33(16) ?
O1 S1 C1 . . 105.45(17) ?
N1 S1 C1 . . 109.69(15) ?
C7 N1 S1 . . 123.6(2) ?
C7 N1 H1N . . 116(2) ?
S1 N1 H1N . . 115(2) ?
C6 C1 C2 . . 120.3(3) ?
C6 C1 S1 . . 120.4(3) ?
C2 C1 S1 . . 119.3(3) ?
C3 C2 C1 . . 119.7(3) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C2 C3 C4 . . 119.5(4) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
C5 C4 C3 . . 121.3(4) ?
C5 C4 Br1 . . 119.0(3) ?
C3 C4 Br1 . . 119.7(3) ?
C6 C5 C4 . . 119.4(4) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C5 C6 C1 . . 119.9(3) ?
C5 C6 H6 . . 120.1 ?
C1 C6 H6 . . 120.1 ?
N1 C7 C12 . . 113.8(3) ?
N1 C7 C8 . . 108.2(3) ?
C12 C7 C8 . . 110.5(4) ?
N1 C7 H7 . . 108.1 ?
C12 C7 H7 . . 108.1 ?
C8 C7 H7 . . 108.1 ?
C9 C8 C7 . . 111.0(4) ?
C9 C8 H8A . . 109.4 ?
C7 C8 H8A . . 109.4 ?
C9 C8 H8B . . 109.4 ?
C7 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
C10 C9 C8 . . 112.5(5) ?
C10 C9 H9A . . 109.1 ?
C8 C9 H9A . . 109.1 ?
C10 C9 H9B . . 109.1 ?
C8 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.8 ?
C9 C10 C11 . . 111.6(5) ?
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 . . 110.9(4) ?
C10 C11 H11A . . 109.5 ?
C12 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
C12 C11 H11B . . 109.5 ?
H11A C11 H11B . . 108.0 ?
C7 C12 C11 . . 112.5(4) ?
C7 C12 H12A . . 109.1 ?
C11 C12 H12A . . 109.1 ?
C7 C12 H12B . . 109.1 ?
C11 C12 H12B . . 109.1 ?
H12A C12 H12B . . 107.8 ?
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
Br1 C4 . 1.893(4) ?
S1 O2 . 1.427(3) ?
S1 O1 . 1.431(3) ?
S1 N1 . 1.591(3) ?
S1 C1 . 1.769(3) ?
N1 C7 . 1.467(5) ?
N1 H1N . 0.88(3) ?
C1 C6 . 1.376(5) ?
C1 C2 . 1.378(5) ?
C2 C3 . 1.372(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.366(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.369(5) ?
C5 C6 . 1.368(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C12 . 1.490(5) ?
C7 C8 . 1.523(5) ?
C7 H7 . 0.9800 ?
C8 C9 . 1.518(8) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.475(8) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.499(7) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.517(6) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 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
C2 H2 O2 1_555 0.93 2.53 2.903(4) 104
C7 H7 O2 1_555 0.98 2.54 2.992(4) 108
N1 H1n O1 2_656 0.88(3) 2.03(3) 2.898(4) 169(3)
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
O2 S1 N1 C7 . . . . 39.2(3) ?
O1 S1 N1 C7 . . . . 168.6(3) ?
C1 S1 N1 C7 . . . . -77.8(3) ?
O2 S1 C1 C6 . . . . -164.1(3) ?
O1 S1 C1 C6 . . . . 68.0(3) ?
N1 S1 C1 C6 . . . . -46.1(3) ?
O2 S1 C1 C2 . . . . 18.8(4) ?
O1 S1 C1 C2 . . . . -109.1(3) ?
N1 S1 C1 C2 . . . . 136.8(3) ?
C6 C1 C2 C3 . . . . -0.8(6) ?
S1 C1 C2 C3 . . . . 176.3(3) ?
C1 C2 C3 C4 . . . . 0.1(6) ?
C2 C3 C4 C5 . . . . 0.8(7) ?
C2 C3 C4 Br1 . . . . -178.4(3) ?
C3 C4 C5 C6 . . . . -1.0(6) ?
Br1 C4 C5 C6 . . . . 178.2(3) ?
C4 C5 C6 C1 . . . . 0.3(6) ?
C2 C1 C6 C5 . . . . 0.6(6) ?
S1 C1 C6 C5 . . . . -176.5(3) ?
S1 N1 C7 C12 . . . . 91.1(4) ?
S1 N1 C7 C8 . . . . -145.7(3) ?
N1 C7 C8 C9 . . . . -178.8(4) ?
C12 C7 C8 C9 . . . . -53.5(6) ?
C7 C8 C9 C10 . . . . 54.4(7) ?
C8 C9 C10 C11 . . . . -55.0(7) ?
C9 C10 C11 C12 . . . . 54.5(7) ?
N1 C7 C12 C11 . . . . 176.7(4) ?
C8 C7 C12 C11 . . . . 54.8(5) ?
C10 C11 C12 C7 . . . . -55.3(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 690039
