#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/29/2232953.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_2232953
loop_
_publ_author_name
Ejaz
'Khan, Islam Ullah'
'Sheikh, Tahir Ali'
'Harrison, William T. A.'
_publ_section_title
;
 N,N'-Bis(3-methylbut-2-enyl)-N,N'-(1,4-phenylene)dibenzenesulfonamide
;
_journal_coeditor_code           SU2338
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3281
_journal_paper_doi               10.1107/S1600536811045661
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C28 H32 N2 O4 S2'
_chemical_formula_moiety         'C28 H32 N2 O4 S2'
_chemical_formula_sum            'C28 H32 N2 O4 S2'
_chemical_formula_weight         524.68
_chemical_name_systematic
;
N,N'-Bis(3-methylbut-2-enyl)-N,N'-(1,4-
phenylene)dibenzenesulfonamide
;
_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                 105.673(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.6574(4)
_cell_length_b                   20.8073(8)
_cell_length_c                   6.4015(2)
_cell_measurement_reflns_used    3403
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      1.96
_cell_volume                     1366.76(9)
_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)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_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'
_diffrn_measurement_method       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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11502
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0391
_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)+(0.0426P)²+0.3607P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                1931
_reflns_number_total             2667
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2338.cif
_cod_data_source_block           I
_cod_original_cell_volume        1366.76(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232953
_cod_database_fobs_code          2232953
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_symmetry_multiplicity
C C1 0.1596(2) 0.38177(9) 0.4486(3) 0.0504(5) Uani d . 1 1
C C2 0.1301(2) 0.33079(11) 0.3050(4) 0.0653(6) Uani d . 1 1
H H2 0.1735 0.2918 0.3386 0.078 Uiso calc R 1 1
C C3 0.0355(3) 0.33861(14) 0.1113(4) 0.0812(8) Uani d . 1 1
H H3 0.0168 0.3050 0.0117 0.097 Uiso calc R 1 1
C C4 -0.0307(3) 0.39525(15) 0.0648(4) 0.0864(8) Uani d . 1 1
H H4 -0.0953 0.3998 -0.0650 0.104 Uiso calc R 1 1
C C5 -0.0026(3) 0.44530(13) 0.2077(4) 0.0780(7) Uani d . 1 1
H H5 -0.0489 0.4836 0.1758 0.094 Uiso calc R 1 1
C C6 0.0940(2) 0.43918(11) 0.3987(4) 0.0617(6) Uani d . 1 1
H H6 0.1149 0.4737 0.4940 0.074 Uiso calc R 1 1
C C7 0.4581(2) 0.32309(9) 0.4971(4) 0.0563(5) Uani d . 1 1
H H7A 0.4214 0.2838 0.5369 0.068 Uiso calc R 1 1
H H7B 0.4229 0.3295 0.3422 0.068 Uiso calc R 1 1
C C8 0.6019(2) 0.31741(9) 0.5505(3) 0.0536(5) Uani d . 1 1
H H8 0.6433 0.3027 0.6892 0.064 Uiso calc R 1 1
C C9 0.6779(2) 0.33075(10) 0.4248(3) 0.0549(5) Uani d . 1 1
C C10 0.8227(3) 0.32188(14) 0.5036(4) 0.0874(8) Uani d . 1 1
H H10A 0.8445 0.3029 0.6456 0.131 Uiso calc R 1 1
H H10B 0.8650 0.3629 0.5101 0.131 Uiso calc R 1 1
H H10C 0.8513 0.2942 0.4057 0.131 Uiso calc R 1 1
C C11 0.6331(3) 0.35544(14) 0.1992(4) 0.0806(8) Uani d . 1 1
H H11A 0.5396 0.3548 0.1524 0.121 Uiso calc R 1 1
H H11B 0.6672 0.3288 0.1051 0.121 Uiso calc R 1 1
H H11C 0.6634 0.3987 0.1943 0.121 Uiso calc R 1 1
C C12 0.45972(18) 0.44109(8) 0.5560(3) 0.0407(4) Uani d . 1 1
C C13 0.41589(19) 0.46298(9) 0.3456(3) 0.0475(5) Uani d . 1 1
H H13 0.3591 0.4380 0.2412 0.057 Uiso calc R 1 1
C C14 0.54372(19) 0.47809(9) 0.7100(3) 0.0471(5) Uani d . 1 1
H H14 0.5734 0.4633 0.8519 0.057 Uiso calc R 1 1
S S1 0.28630(5) 0.37450(2) 0.68836(8) 0.05203(19) Uani d . 1 1
N N1 0.42238(16) 0.37861(7) 0.6175(2) 0.0466(4) Uani d . 1 1
O O1 0.28181(15) 0.42921(7) 0.8196(2) 0.0655(4) Uani d . 1 1
O O2 0.28035(15) 0.31145(7) 0.7724(3) 0.0727(5) Uani d . 1 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
C6 C1 C2 . . 120.1(2)
C6 C1 S1 . . 120.00(16)
C2 C1 S1 . . 119.85(17)
C3 C2 C1 . . 119.1(2)
C3 C2 H2 . . 120.5
C1 C2 H2 . . 120.5
C4 C3 C2 . . 120.5(2)
C4 C3 H3 . . 119.8
C2 C3 H3 . . 119.8
C3 C4 C5 . . 120.4(3)
C3 C4 H4 . . 119.8
C5 C4 H4 . . 119.8
C4 C5 C6 . . 120.1(2)
C4 C5 H5 . . 120.0
C6 C5 H5 . . 120.0
C5 C6 C1 . . 119.9(2)
C5 C6 H6 . . 120.1
C1 C6 H6 . . 120.1
C8 C7 N1 . . 109.54(16)
C8 C7 H7A . . 109.8
N1 C7 H7A . . 109.8
C8 C7 H7B . . 109.8
N1 C7 H7B . . 109.8
H7A C7 H7B . . 108.2
C9 C8 C7 . . 127.64(19)
C9 C8 H8 . . 116.2
C7 C8 H8 . . 116.2
C8 C9 C11 . . 125.3(2)
C8 C9 C10 . . 121.0(2)
C11 C9 C10 . . 113.7(2)
C9 C10 H10A . . 109.5
C9 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
C9 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C9 C11 H11A . . 109.5
C9 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C9 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
C14 C12 C13 . . 119.93(16)
C14 C12 N1 . . 118.85(15)
C13 C12 N1 . . 121.18(16)
C14 C13 C12 3_666 . 119.95(17)
C14 C13 H13 3_666 . 120.0
C12 C13 H13 . . 120.0
C12 C14 C13 . 3_666 120.12(16)
C12 C14 H14 . . 119.9
C13 C14 H14 3_666 . 119.9
O1 S1 O2 . . 120.08(9)
O1 S1 N1 . . 107.20(9)
O2 S1 N1 . . 106.63(9)
O1 S1 C1 . . 107.84(9)
O2 S1 C1 . . 107.89(10)
N1 S1 C1 . . 106.46(8)
C12 N1 C7 . . 115.31(14)
C12 N1 S1 . . 116.94(12)
C7 N1 S1 . . 118.15(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.378(3)
C1 C2 . 1.383(3)
C1 S1 . 1.756(2)
C2 C3 . 1.381(3)
C2 H2 . 0.9300
C3 C4 . 1.364(4)
C3 H3 . 0.9300
C4 C5 . 1.365(4)
C4 H4 . 0.9300
C5 C6 . 1.375(3)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 C8 . 1.482(3)
C7 N1 . 1.494(2)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 C9 . 1.317(3)
C8 H8 . 0.9300
C9 C11 . 1.485(3)
C9 C10 . 1.500(3)
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
C11 H11A . 0.9600
C11 H11B . 0.9600
C11 H11C . 0.9600
C12 C14 . 1.374(2)
C12 C13 . 1.379(2)
C12 N1 . 1.445(2)
C13 C14 3_666 1.378(2)
C13 H13 . 0.9300
C14 C13 3_666 1.378(2)
C14 H14 . 0.9300
S1 O1 . 1.4233(14)
S1 O2 . 1.4257(14)
S1 N1 . 1.6345(16)
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 4_565 0.93 2.52 3.398(3) 158
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_4
_geom_torsion
C6 C1 C2 C3 . 0.7(3)
S1 C1 C2 C3 . -176.16(17)
C1 C2 C3 C4 . -1.9(4)
C2 C3 C4 C5 . 1.1(4)
C3 C4 C5 C6 . 0.8(4)
C4 C5 C6 C1 . -2.0(4)
C2 C1 C6 C5 . 1.2(3)
S1 C1 C6 C5 . 178.08(17)
N1 C7 C8 C9 . -108.2(2)
C7 C8 C9 C11 . 0.7(4)
C7 C8 C9 C10 . -179.6(2)
C14 C12 C13 C14 3_666 -0.1(3)
N1 C12 C13 C14 3_666 -177.99(17)
C13 C12 C14 C13 3_666 0.1(3)
N1 C12 C14 C13 3_666 178.04(17)
C6 C1 S1 O1 . 12.14(19)
C2 C1 S1 O1 . -170.99(16)
C6 C1 S1 O2 . 143.23(16)
C2 C1 S1 O2 . -39.90(18)
C6 C1 S1 N1 . -102.63(17)
C2 C1 S1 N1 . 74.23(17)
C14 C12 N1 C7 . -119.44(19)
C13 C12 N1 C7 . 58.5(2)
C14 C12 N1 S1 . 94.90(18)
C13 C12 N1 S1 . -87.15(19)
C8 C7 N1 C12 . 65.6(2)
C8 C7 N1 S1 . -149.18(14)
O1 S1 N1 C12 . -41.56(15)
O2 S1 N1 C12 . -171.36(13)
C1 S1 N1 C12 . 73.64(15)
O1 S1 N1 C7 . 173.77(14)
O2 S1 N1 C7 . 43.97(17)
C1 S1 N1 C7 . -71.02(16)
