#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/50/2215049.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_2215049
loop_
_publ_author_name
'Yue Meng'
'Guang-Xiang Zhong'
'Wei-Xiao Hu'
_publ_section_title
;
 N-(2-Bromo-1-phenylethyl)-4-methylbenzenesulfonamide
;
_journal_coeditor_code           CI2421
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3744
_journal_page_last               o3744
_journal_paper_doi               10.1107/S1600536807038445
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H16 Br N O2 S'
_chemical_formula_moiety         'C15 H16 Br N O2 S'
_chemical_formula_sum            'C15 H16 Br N O2 S'
_chemical_formula_weight         354.26
_chemical_name_systematic
;
N-(2-Bromo-1-phenylethyl)-4-methylbenzenesulfonamide
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 97.280(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8866(13)
_cell_length_b                   9.5474(16)
_cell_length_c                   10.2881(16)
_cell_measurement_reflns_used    1415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.33
_cell_measurement_theta_min      2.6
_cell_volume                     768.4(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2005)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Bruker SMART 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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4943
_diffrn_reflns_theta_full        28.38
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.811
_exptl_absorpt_correction_T_max  0.56
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1873
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0374
_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)+(0.0375P)²+0.4403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                1211
_reflns_number_total             1873
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2421.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2215049
_cod_database_fobs_code          2215049
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
Br Br1 0.83529(7) 0.2500 0.77727(4) 0.0852(2) Uani d S 1
S S1 0.39919(13) 0.2500 0.45965(10) 0.0614(3) Uani d S 1
O O1 0.3345(5) 0.1259(2) 0.5024(2) 0.1211(11) Uani d . 1
N N1 0.5905(5) 0.1825(4) 0.5114(4) 0.0517(10) Uani d P 0.50
H H1N 0.6121 0.0939 0.5025 0.047(14) Uiso d PR 0.50
C C1 0.3791(5) 0.2500 0.2874(3) 0.0509(9) Uani d S 1
C C2 0.3740(4) 0.1250(3) 0.2209(3) 0.0626(7) Uani d . 1
H H2 0.3767 0.0405 0.2662 0.075 Uiso calc R 1
C C3 0.3647(4) 0.1264(4) 0.0858(3) 0.0696(8) Uani d . 1
H H3 0.3601 0.0419 0.0406 0.084 Uiso calc R 1
C C4 0.3621(5) 0.2500 0.0166(4) 0.0640(11) Uani d S 1
C C5 0.3536(7) 0.2500 -0.1320(4) 0.0944(17) Uani d S 1
H H5A 0.4675 0.2500 -0.1557 0.142 Uiso d SR 1
H H5B 0.2941 0.3321 -0.1670 0.142 Uiso d PR 0.50
H H5C 0.2941 0.1679 -0.1670 0.142 Uiso d PR 0.50
C C6 0.7406(5) 0.2500 0.4975(4) 0.0647(11) Uani d S 1
H H6 0.7030 0.3453 0.5021 0.078 Uiso d PR 0.50
C C7 0.8864(6) 0.2500 0.5997(4) 0.0940(17) Uani d S 1
H H7A 0.9556 0.3319 0.5875 0.113 Uiso calc PR 0.50
H H7B 0.9556 0.1681 0.5875 0.113 Uiso calc PR 0.50
C C8 0.8036(5) 0.2500 0.3641(4) 0.0576(10) Uani d S 1
C C9 0.8369(4) 0.1261(4) 0.3045(3) 0.0771(9) Uani d . 1
H H9 0.8145 0.0414 0.3436 0.093 Uiso calc R 1
C C10 0.9037(4) 0.1267(5) 0.1866(3) 0.0924(11) Uani d . 1
H H10 0.9256 0.0424 0.1466 0.111 Uiso calc R 1
C C11 0.9375(6) 0.2500 0.1287(4) 0.0878(17) Uani d S 1
H H11 0.9836 0.2500 0.0498 0.105 Uiso calc SR 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'
Br Br -0.2901 2.4595 '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
O1 S1 O1 4_565 . 117.9(2)
O1 S1 N1 4_565 4_565 85.6(2)
O1 S1 N1 . 4_565 125.8(2)
O1 S1 N1 4_565 . 125.8(2)
O1 S1 N1 . . 85.6(2)
O1 S1 C1 4_565 . 109.29(12)
O1 S1 C1 . . 109.29(12)
N1 S1 C1 4_565 . 106.52(18)
N1 S1 C1 . . 106.52(18)
N1 N1 C6 4_565 . 61.97(19)
N1 N1 S1 4_565 . 67.23(15)
C6 N1 S1 . . 123.0(3)
N1 N1 H1N 4_565 . 166.5
C6 N1 H1N . . 105.3
S1 N1 H1N . . 121.6
C2 C1 C2 . 4_565 120.6(3)
C2 C1 S1 . . 119.67(17)
C2 C1 S1 4_565 . 119.67(17)
C1 C2 C3 . . 119.1(3)
C1 C2 H2 . . 120.4
C3 C2 H2 . . 120.4
C4 C3 C2 . . 121.6(3)
C4 C3 H3 . . 119.2
C2 C3 H3 . . 119.2
C3 C4 C3 4_565 . 117.9(4)
C3 C4 C5 4_565 . 121.03(19)
C3 C4 C5 . . 121.03(19)
C4 C5 H5A . . 109.3
C4 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
C4 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
N1 C6 N1 . 4_565 56.1(4)
N1 C6 C7 . . 122.5(3)
N1 C6 C7 4_565 . 122.5(3)
N1 C6 C8 . . 118.7(3)
N1 C6 C8 4_565 . 118.7(3)
C7 C6 C8 . . 109.5(3)
N1 C6 H6 . . 99.5
C7 C6 H6 . . 100.6
C8 C6 H6 . . 100.6
C6 C7 Br1 . . 116.4(3)
C6 C7 H7A . . 108.2
Br1 C7 H7A . . 108.2
C6 C7 H7B . . 108.2
Br1 C7 H7B . . 108.2
H7A C7 H7B . . 107.3
C9 C8 C9 4_565 . 119.0(4)
C9 C8 C6 4_565 . 120.44(19)
C9 C8 C6 . . 120.44(19)
C8 C9 C10 . . 120.2(4)
C8 C9 H9 . . 119.9
C10 C9 H9 . . 119.9
C11 C10 C9 . . 120.4(4)
C11 C10 H10 . . 119.8
C9 C10 H10 . . 119.8
C10 C11 C10 4_565 . 119.8(4)
C10 C11 H11 4_565 . 120.1
C10 C11 H11 . . 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C7 . 1.920(4)
S1 O1 4_565 1.384(2)
S1 O1 . 1.384(2)
S1 N1 4_565 1.665(4)
S1 N1 . 1.665(4)
S1 C1 . 1.759(4)
N1 N1 4_565 1.289(8)
N1 C6 . 1.371(5)
N1 H1N . 0.87
C1 C2 . 1.374(3)
C1 C2 4_565 1.374(3)
C2 C3 . 1.382(4)
C2 H2 . 0.93
C3 C4 . 1.377(4)
C3 H3 . 0.93
C4 C3 4_565 1.377(4)
C4 C5 . 1.522(6)
C5 H5A . 0.96
C5 H5B . 0.96
C5 H5C . 0.96
C6 N1 4_565 1.371(5)
C6 C7 . 1.457(6)
C6 C8 . 1.518(5)
C6 H6 . 0.96
C7 H7A . 0.97
C7 H7B . 0.97
C8 C9 4_565 1.373(4)
C8 C9 . 1.373(4)
C9 C10 . 1.383(4)
C9 H9 . 0.93
C10 C11 . 1.361(5)
C10 H10 . 0.93
C11 C10 4_565 1.361(5)
C11 H11 . 0.93
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
N1 H1N O1 3_656 0.87 2.14 3.010(5) 175
C11 H11 Br1 1_554 0.93 2.90 3.603(4) 134
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_4
_geom_torsion
O1 S1 N1 N1 4_565 4_565 -32.58(15)
O1 S1 N1 N1 . 4_565 -154.03(12)
C1 S1 N1 N1 . 4_565 97.15(9)
O1 S1 N1 C6 4_565 . -61.0(4)
O1 S1 N1 C6 . . 177.6(3)
N1 S1 N1 C6 4_565 . -28.4(4)
C1 S1 N1 C6 . . 68.8(3)
O1 S1 C1 C2 4_565 . -156.1(3)
O1 S1 C1 C2 . . -25.8(4)
N1 S1 C1 C2 4_565 . 112.8(3)
N1 S1 C1 C2 . . 65.2(3)
O1 S1 C1 C2 4_565 4_565 25.8(4)
O1 S1 C1 C2 . 4_565 156.1(3)
N1 S1 C1 C2 4_565 4_565 -65.2(3)
N1 S1 C1 C2 . 4_565 -112.8(3)
C2 C1 C2 C3 4_565 . 0.4(6)
S1 C1 C2 C3 . . -177.6(2)
C1 C2 C3 C4 . . 0.6(5)
C2 C3 C4 C3 . 4_565 -1.6(6)
C2 C3 C4 C5 . . 179.4(3)
S1 N1 C6 N1 . 4_565 29.8(4)
N1 N1 C6 C7 4_565 . 109.9(3)
S1 N1 C6 C7 . . 139.6(3)
N1 N1 C6 C8 4_565 . -107.0(3)
S1 N1 C6 C8 . . -77.2(3)
N1 C6 C7 Br1 . . -33.9(3)
N1 C6 C7 Br1 4_565 . 33.9(3)
C8 C6 C7 Br1 . . 180.0
N1 C6 C8 C9 . 4_565 124.2(3)
N1 C6 C8 C9 4_565 4_565 59.4(5)
C7 C6 C8 C9 . 4_565 -88.2(3)
N1 C6 C8 C9 . . -59.4(5)
N1 C6 C8 C9 4_565 . -124.2(3)
C7 C6 C8 C9 . . 88.2(3)
C9 C8 C9 C10 4_565 . 0.3(6)
C6 C8 C9 C10 . . -176.3(3)
C8 C9 C10 C11 . . 0.2(6)
C9 C10 C11 C10 . 4_565 -0.7(7)
