#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/55/2235576.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_2235576
loop_
_publ_author_name
'Al-Mohammed, Nassir N.'
'Alias, Yatimah'
'Abdullah, Zanariah'
'Khaledi, Hamid'
_publ_section_title
;
 N,N'-{[Ethane-1,2-diylbis(oxy)]bis(ethane-2,1-diyl)}bis(4-methylbenzenesulfonamide)
;
_journal_coeditor_code           PV2551
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1983
_journal_paper_doi               10.1107/S1600536812024324
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C20 H28 N2 O6 S2'
_chemical_formula_moiety         'C20 H28 N2 O6 S2'
_chemical_formula_sum            'C20 H28 N2 O6 S2'
_chemical_formula_weight         456.56
_chemical_name_systematic
;
N,N'-{[Ethane-1,2-diylbis(oxy)]bis(ethane-2,1-diyl)}bis(4-
methylbenzenesulfonamide)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 93.680(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.135(7)
_cell_length_b                   9.220(6)
_cell_length_c                   21.452(15)
_cell_measurement_reflns_used    1589
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.65
_cell_measurement_theta_min      2.87
_cell_volume                     2198(3)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0554
_diffrn_reflns_av_sigmaI/netI    0.0666
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5135
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.357
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1983
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0533
_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)+(0.0846P)²+0.5056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1504
_reflns_number_gt                1558
_reflns_number_total             1983
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            pv2551.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235576
_cod_database_fobs_code          2235576
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_symmetry_multiplicity
S S1 0.51163(5) 0.03617(7) 0.64470(3) 0.0440(3) Uani d . 1 1
O O1 0.48265(19) -0.0655(2) 0.59612(9) 0.0590(6) Uani d . 1 1
O O2 0.41953(16) 0.0823(2) 0.68398(9) 0.0561(5) Uani d . 1 1
O O3 0.87638(18) 0.0318(2) 0.72055(10) 0.0567(6) Uani d . 1 1
N N1 0.6163(2) -0.0329(2) 0.69058(11) 0.0464(6) Uani d D 1 1
H H1 0.614(3) 0.002(3) 0.7255(9) 0.056 Uiso d D 1 1
C C1 0.7115(3) 0.5726(4) 0.52722(19) 0.0769(10) Uani d . 1 1
H H1A 0.7314 0.6430 0.5592 0.115 Uiso calc R 1 1
H H1B 0.6528 0.6126 0.4973 0.115 Uiso calc R 1 1
H H1C 0.7827 0.5473 0.5066 0.115 Uiso calc R 1 1
C C2 0.6609(2) 0.4389(3) 0.55625(15) 0.0518(7) Uani d . 1 1
C C3 0.6610(2) 0.4248(3) 0.62001(15) 0.0533(7) Uani d . 1 1
H H3 0.6933 0.4992 0.6452 0.064 Uiso calc R 1 1
C C4 0.6151(2) 0.3047(3) 0.64781(13) 0.0488(7) Uani d . 1 1
H H4 0.6153 0.2980 0.6911 0.059 Uiso calc R 1 1
C C5 0.5681(2) 0.1927(3) 0.60972(12) 0.0398(6) Uani d . 1 1
C C6 0.5678(2) 0.2038(3) 0.54560(13) 0.0512(7) Uani d . 1 1
H H6 0.5374 0.1288 0.5202 0.061 Uiso calc R 1 1
C C7 0.6131(3) 0.3270(3) 0.51958(14) 0.0594(8) Uani d . 1 1
H H7 0.6116 0.3352 0.4763 0.071 Uiso calc R 1 1
C C8 0.7215(3) -0.1019(3) 0.66646(15) 0.0578(8) Uani d . 1 1
H H8A 0.6986 -0.1426 0.6257 0.069 Uiso calc R 1 1
H H8B 0.7461 -0.1816 0.6939 0.069 Uiso calc R 1 1
C C9 0.8272(3) -0.0037(4) 0.66034(14) 0.0566(8) Uani d . 1 1
H H9A 0.8873 -0.0518 0.6369 0.068 Uiso calc R 1 1
H H9B 0.8019 0.0839 0.6381 0.068 Uiso calc R 1 1
C C10 0.9623(3) 0.1465(3) 0.72024(14) 0.0570(8) Uani d . 1 1
H H10A 0.9210 0.2387 0.7150 0.068 Uiso calc R 1 1
H H10B 1.0129 0.1338 0.6855 0.068 Uiso calc R 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
O1 S1 O2 . . 119.26(13)
O1 S1 N1 . . 108.00(13)
O2 S1 N1 . . 106.01(13)
O1 S1 C5 . . 107.33(13)
O2 S1 C5 . . 107.22(13)
N1 S1 C5 . . 108.68(12)
C9 O3 C10 . . 112.9(2)
C8 N1 S1 . . 121.6(2)
C8 N1 H1 . . 124(2)
S1 N1 H1 . . 110(2)
C2 C1 H1A . . 109.5
C2 C1 H1B . . 109.5
H1A C1 H1B . . 109.5
C2 C1 H1C . . 109.5
H1A C1 H1C . . 109.5
H1B C1 H1C . . 109.5
C3 C2 C7 . . 118.2(3)
C3 C2 C1 . . 120.8(3)
C7 C2 C1 . . 121.0(3)
C4 C3 C2 . . 122.2(3)
C4 C3 H3 . . 118.9
C2 C3 H3 . . 118.9
C3 C4 C5 . . 118.6(3)
C3 C4 H4 . . 120.7
C5 C4 H4 . . 120.7
C6 C5 C4 . . 120.3(2)
C6 C5 S1 . . 120.5(2)
C4 C5 S1 . . 119.1(2)
C7 C6 C5 . . 119.2(3)
C7 C6 H6 . . 120.4
C5 C6 H6 . . 120.4
C6 C7 C2 . . 121.5(3)
C6 C7 H7 . . 119.2
C2 C7 H7 . . 119.2
N1 C8 C9 . . 114.9(2)
N1 C8 H8A . . 108.5
C9 C8 H8A . . 108.5
N1 C8 H8B . . 108.5
C9 C8 H8B . . 108.5
H8A C8 H8B . . 107.5
O3 C9 C8 . . 108.8(2)
O3 C9 H9A . . 109.9
C8 C9 H9A . . 109.9
O3 C9 H9B . . 109.9
C8 C9 H9B . . 109.9
H9A C9 H9B . . 108.3
O3 C10 C10 . 2_756 109.8(2)
O3 C10 H10A . . 109.7
C10 C10 H10A 2_756 . 109.7
O3 C10 H10B . . 109.7
C10 C10 H10B 2_756 . 109.7
H10A C10 H10B . . 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O1 . 1.423(2)
S1 O2 . 1.433(2)
S1 N1 . 1.608(2)
S1 C5 . 1.761(3)
O3 C9 . 1.409(3)
O3 C10 . 1.426(3)
N1 C8 . 1.457(4)
N1 H1 . 0.816(17)
C1 C2 . 1.507(4)
C1 H1A . 0.9600
C1 H1B . 0.9600
C1 H1C . 0.9600
C2 C3 . 1.374(4)
C2 C7 . 1.383(4)
C3 C4 . 1.372(4)
C3 H3 . 0.9300
C4 C5 . 1.398(4)
C4 H4 . 0.9300
C5 C6 . 1.379(4)
C6 C7 . 1.376(4)
C6 H6 . 0.9300
C7 H7 . 0.9300
C8 C9 . 1.497(4)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C10 2_756 1.482(6)
C10 H10A . 0.9700
C10 H10B . 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
N1 H1 O2 2_656 0.816(17) 2.135(18) 2.944(3) 171(3)
C6 H6 O1 5_656 0.93 2.56 3.311(4) 138.2
