#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/98/2229858.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_2229858
loop_
_publ_author_name
'Rodrigues, Vinola Z.'
'Foro, Sabine'
'Gowda, B. Thimme'
_publ_section_title
;
 N,N'-Bis(2-chlorophenylsulfonyl)suberamide
;
_journal_coeditor_code           TK2727
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o884
_journal_paper_doi               10.1107/S1600536811009196
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H22 Cl2 N2 O6 S2'
_chemical_formula_moiety         'C20 H22 Cl2 N2 O6 S2'
_chemical_formula_sum            'C20 H22 Cl2 N2 O6 S2'
_chemical_formula_weight         521.42
_chemical_name_common
;
N,N'-Bis(2-chlorophenylsulfonyl)suberamide
;
_chemical_name_systematic
;
N,N'-Bis(2-chlorophenylsulfonyl)octanediamide
;
_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                 94.575(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.8737(9)
_cell_length_b                   9.7170(10)
_cell_length_c                   14.616(2)
_cell_measurement_reflns_used    1476
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.74
_cell_measurement_theta_min      2.59
_cell_volume                     1114.7(2)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using 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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4126
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.60
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_T_max  0.9498
_exptl_absorpt_correction_T_min  0.8349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0377
_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)+(0.0588P)²+0.1117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                1744
_reflns_number_total             2276
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2727.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229858
_cod_database_fobs_code          2229858
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
C C1 0.3294(3) -0.0856(2) 0.61075(13) 0.0301(5) Uani d . 1 . .
C C2 0.2763(3) -0.0520(2) 0.52035(14) 0.0329(5) Uani d . 1 . .
C C3 0.3042(3) -0.1437(3) 0.45110(15) 0.0449(6) Uani d . 1 . .
H H3 0.2664 -0.1228 0.3908 0.054 Uiso calc R 1 . .
C C4 0.3873(4) -0.2654(3) 0.47050(17) 0.0499(7) Uani d . 1 . .
H H4 0.4073 -0.3258 0.4232 0.060 Uiso calc R 1 . .
C C5 0.4412(3) -0.2986(3) 0.55920(18) 0.0479(6) Uani d . 1 . .
H H5 0.4977 -0.3813 0.5719 0.057 Uiso calc R 1 . .
C C6 0.4118(3) -0.2096(2) 0.62958(16) 0.0381(5) Uani d . 1 . .
H H6 0.4473 -0.2327 0.6898 0.046 Uiso calc R 1 . .
C C7 0.0104(3) -0.0734(2) 0.75061(14) 0.0306(5) Uani d . 1 . .
C C8 -0.1521(3) -0.0352(2) 0.79001(14) 0.0347(5) Uani d . 1 . .
H H8A -0.2460 -0.0863 0.7594 0.042 Uiso calc R 1 . .
H H8B -0.1743 0.0622 0.7808 0.042 Uiso calc R 1 . .
C C9 -0.1371(3) -0.0685(2) 0.89303(14) 0.0385(6) Uani d . 1 . .
H H9A -0.2477 -0.0554 0.9167 0.046 Uiso calc R 1 . .
H H9B -0.1066 -0.1647 0.9011 0.046 Uiso calc R 1 . .
C C10 -0.0071(3) 0.0185(3) 0.94906(14) 0.0394(6) Uani d . 1 . .
H H10A -0.0384 0.1147 0.9422 0.047 Uiso calc R 1 . .
H H10B 0.1034 0.0065 0.9252 0.047 Uiso calc R 1 . .
N N1 0.1046(2) 0.03505(19) 0.72033(12) 0.0316(4) Uani d D 1 . .
H H1N 0.066(3) 0.1134(18) 0.7259(16) 0.038 Uiso d D 1 . .
O O1 0.3959(2) -0.03761(18) 0.78343(10) 0.0456(4) Uani d . 1 . .
O O2 0.3555(2) 0.16371(17) 0.68236(10) 0.0415(4) Uani d . 1 . .
O O3 0.0630(2) -0.19135(16) 0.74794(11) 0.0437(4) Uani d . 1 . .
Cl Cl1 0.17624(9) 0.10214(7) 0.49044(4) 0.0505(2) Uani d . 1 . .
S S1 0.31012(7) 0.02626(6) 0.70503(3) 0.03155(17) Uani d . 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'
Cl Cl 0.1484 0.1585 '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
C6 C1 C2 . . 119.5(2) ?
C6 C1 S1 . . 116.55(16) ?
C2 C1 S1 . . 123.79(17) ?
C3 C2 C1 . . 119.4(2) ?
C3 C2 Cl1 . . 118.01(18) ?
C1 C2 Cl1 . . 122.59(17) ?
C4 C3 C2 . . 120.5(2) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C5 C4 C3 . . 120.4(2) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.1(2) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C5 C6 C1 . . 120.1(2) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
O3 C7 N1 . . 120.9(2) ?
O3 C7 C8 . . 123.3(2) ?
N1 C7 C8 . . 115.66(19) ?
C7 C8 C9 . . 108.97(18) ?
C7 C8 H8A . . 109.9 ?
C9 C8 H8A . . 109.9 ?
C7 C8 H8B . . 109.9 ?
C9 C8 H8B . . 109.9 ?
H8A C8 H8B . . 108.3 ?
C10 C9 C8 . . 114.08(18) ?
C10 C9 H9A . . 108.7 ?
C8 C9 H9A . . 108.7 ?
C10 C9 H9B . . 108.7 ?
C8 C9 H9B . . 108.7 ?
H9A C9 H9B . . 107.6 ?
C9 C10 C10 . 3_557 112.9(2) ?
C9 C10 H10A . . 109.0 ?
C10 C10 H10A 3_557 . 109.0 ?
C9 C10 H10B . . 109.0 ?
C10 C10 H10B 3_557 . 109.0 ?
H10A C10 H10B . . 107.8 ?
C7 N1 S1 . . 124.07(16) ?
C7 N1 H1N . . 117.4(17) ?
S1 N1 H1N . . 115.6(17) ?
O1 S1 O2 . . 118.86(10) ?
O1 S1 N1 . . 108.65(10) ?
O2 S1 N1 . . 104.39(10) ?
O1 S1 C1 . . 107.08(11) ?
O2 S1 C1 . . 110.79(10) ?
N1 S1 C1 . . 106.41(10) ?
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
C1 C6 . 1.385(3) ?
C1 C2 . 1.393(3) ?
C1 S1 . 1.771(2) ?
C2 C3 . 1.379(3) ?
C2 Cl1 . 1.732(2) ?
C3 C4 . 1.370(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.370(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.378(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O3 . 1.221(3) ?
C7 N1 . 1.381(3) ?
C7 C8 . 1.492(3) ?
C8 C9 . 1.535(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.516(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C10 3_557 1.527(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
N1 S1 . 1.6532(19) ?
N1 H1N . 0.826(16) ?
O1 S1 . 1.4250(16) ?
O2 S1 . 1.4282(17) ?
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 O3 2_556 0.826(16) 2.200(16) 3.020(2) 172(2)
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
C6 C1 C2 C3 . . . . 1.0(3) ?
S1 C1 C2 C3 . . . . 176.93(18) ?
C6 C1 C2 Cl1 . . . . -178.69(17) ?
S1 C1 C2 Cl1 . . . . -2.8(3) ?
C1 C2 C3 C4 . . . . -1.7(4) ?
Cl1 C2 C3 C4 . . . . 178.1(2) ?
C2 C3 C4 C5 . . . . 1.1(4) ?
C3 C4 C5 C6 . . . . 0.1(4) ?
C4 C5 C6 C1 . . . . -0.7(4) ?
C2 C1 C6 C5 . . . . 0.2(3) ?
S1 C1 C6 C5 . . . . -176.03(19) ?
O3 C7 C8 C9 . . . . 64.1(3) ?
N1 C7 C8 C9 . . . . -113.0(2) ?
C7 C8 C9 C10 . . . . 66.2(3) ?
C8 C9 C10 C10 . . . 3_557 -179.1(2) ?
O3 C7 N1 S1 . . . . -17.2(3) ?
C8 C7 N1 S1 . . . . 160.00(15) ?
C7 N1 S1 O1 . . . . -46.8(2) ?
C7 N1 S1 O2 . . . . -174.61(16) ?
C7 N1 S1 C1 . . . . 68.16(19) ?
C6 C1 S1 O1 . . . . 2.7(2) ?
C2 C1 S1 O1 . . . . -173.29(18) ?
C6 C1 S1 O2 . . . . 133.79(17) ?
C2 C1 S1 O2 . . . . -42.2(2) ?
C6 C1 S1 N1 . . . . -113.32(17) ?
C2 C1 S1 N1 . . . . 70.6(2) ?
