#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/09/2200932.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_2200932
loop_
_publ_author_name
'Sethu Sankar, K.'
'Suresh Babu, N.'
'Velmurugan, D.'
'Shanmuga Sundara Raj, S.'
'Fun, H.-K.'
_publ_section_title
;
 1,2-Bis(1-phenylsulfonyl-3-phenylthioindol-2-yl)ethane
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o134
_journal_page_last               o136
_journal_paper_doi               10.1107/S1600536802000405
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C42 H32 N2 O4 S4'
_chemical_formula_moiety         'C42 H32 N2 O4 S4'
_chemical_formula_sum            'C42 H32 N2 O4 S4'
_chemical_formula_weight         756.94
_chemical_name_systematic
;
1,2-Bis(1'-Phenylsulfonyl-3-phenylthioindole-2-yl)ethane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.8810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.5439(4)
_cell_length_b                   8.3686(2)
_cell_length_c                   18.9898(6)
_cell_measurement_reflns_used    13390
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.33
_cell_measurement_theta_min      1.74
_cell_volume                     1907.55(10)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1999)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1983, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0859
_diffrn_reflns_av_sigmaI/netI    .1130
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12921
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        <2
_exptl_absorpt_coefficient_mu    .294
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             788
_exptl_crystal_size_max          .46
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .12
_refine_diff_density_max         .238
_refine_diff_density_min         -.310
_refine_ls_extinction_coef       .0046(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   .928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .928
_refine_ls_R_factor_all          .1455
_refine_ls_R_factor_gt           .0563
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0499P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1180
_refine_ls_wR_factor_ref         .1442
_reflns_number_gt                2139
_reflns_number_total             4615
_reflns_threshold_expression     I>2\sa(I)
_cod_data_source_file            na6129.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2200932
_cod_database_fobs_code          2200932
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
S1 .29178(6) .55196(9) .04830(5) .0586(3) Uani d . 1 . . S
S2 -.07563(6) .76266(10) -.16165(5) .0645(3) Uani d . 1 . . S
N1 .20069(16) .5642(2) -.03547(12) .0420(6) Uani d . 1 . . N
O1 .38114(17) .4551(2) .04055(14) .0829(8) Uani d . 1 . . O
O2 .23027(19) .5045(3) .09667(12) .0828(8) Uani d . 1 . . O
C1 .0170(2) .5885(3) .00010(14) .0429(7) Uani d . 1 . . C
H1A -.0497 .6537 -.0155 .051 Uiso calc R 1 . . H
H1B .0573 .6197 .0499 .051 Uiso calc R 1 . . H
C2 .0879(2) .6209(3) -.04908(14) .0392(6) Uani d . 1 . . C
C3 .0575(2) .6885(3) -.11646(15) .0428(7) Uani d . 1 . . C
C4 .1481(2) .6820(3) -.14851(15) .0459(7) Uani d . 1 . . C
C5 .1604(3) .7321(4) -.21518(19) .0723(10) Uani d . 1 . . C
H5 .1015 .7808 -.2500 .087 Uiso calc R 1 . . H
C6 .2603(4) .7089(5) -.2293(2) .0881(12) Uani d . 1 . . C
H6 .2690 .7423 -.2741 .106 Uiso calc R 1 . . H
C7 .3480(3) .6370(5) -.1783(2) .0834(12) Uani d . 1 . . C
H7 .4150 .6226 -.1892 .100 Uiso calc R 1 . . H
C8 .3388(3) .5856(4) -.1114(2) .0663(9) Uani d . 1 . . C
H8 .3986 .5380 -.0769 .080 Uiso calc R 1 . . H
C9 .2370(2) .6075(3) -.09721(15) .0440(7) Uani d . 1 . . C
C10 .3400(2) .7488(4) .06822(16) .0543(8) Uani d . 1 . . C
C11 .4469(3) .7877(4) .0712(2) .0890(12) Uani d . 1 . . C
H11 .4952 .7100 .0632 .107 Uiso calc R 1 . . H
C12 .4831(4) .9437(5) .0862(3) .1051(15) Uani d . 1 . . C
H12 .5568 .9697 .0907 .126 Uiso calc R 1 . . H
C13 .4118(4) 1.0582(5) .0943(2) .0965(13) Uani d . 1 . . C
H13 .4366 1.1630 .1036 .116 Uiso calc R 1 . . H
C14 .3047(4) 1.0221(5) .0890(3) .1148(17) Uani d . 1 . . C
H14 .2558 1.1023 .0935 .138 Uiso calc R 1 . . H
C15 .2682(3) .8669(5) .0770(2) .0937(13) Uani d . 1 . . C
H15 .1951 .8415 .0749 .112 Uiso calc R 1 . . H
C16 -.0470(2) .9670(3) -.17332(16) .0478(7) Uani d . 1 . . C
C17 -.1249(3) 1.0488(4) -.22860(17) .0619(9) Uani d . 1 . . C
H17 -.1873 .9956 -.2577 .074 Uiso calc R 1 . . H
C18 -.1101(3) 1.2062(5) -.2403(2) .0765(11) Uani d . 1 . . C
H18 -.1632 1.2598 -.2772 .092 Uiso calc R 1 . . H
C19 -.0196(4) 1.2866(4) -.1994(2) .0762(11) Uani d . 1 . . C
H19 -.0106 1.3942 -.2086 .091 Uiso calc R 1 . . H
C20 .0590(3) 1.2085(4) -.14413(19) .0681(10) Uani d . 1 . . C
H20 .1216 1.2629 -.1160 .082 Uiso calc R 1 . . H
C21 .0443(3) 1.0487(4) -.13063(17) .0572(8) Uani d . 1 . . C
H21 .0963 .9963 -.0926 .069 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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
O2 S1 O1 . . 120.01(15) ?
O2 S1 N1 . . 106.50(10) y
O1 S1 N1 . . 106.10(10) y
O2 S1 C10 . . 110.0(2) y
O1 S1 C10 . . 108.80(10) y
N1 S1 C10 . . 104.20(10) y
C3 S2 C16 . . 101.75(13) ?
C9 N1 C2 . . 107.5(2) y
C9 N1 S1 . . 120.41(18) ?
C2 N1 S1 . . 123.7(2) y
C2 C1 C1 . 3_565 112.9(3) ?
C2 C1 H1A . . 109.0 ?
C1 C1 H1A 3_565 . 109.0 ?
C2 C1 H1B . . 109.0 ?
C1 C1 H1B 3_565 . 109.0 ?
H1A C1 H1B . . 107.8 ?
C3 C2 N1 . . 107.5(2) y
C3 C2 C1 . . 127.9(2) y
N1 C2 C1 . . 124.1(2) ?
C2 C3 C4 . . 110.2(2) ?
C2 C3 S2 . . 125.4(2) ?
C4 C3 S2 . . 124.3(2) ?
C5 C4 C9 . . 119.6(3) ?
C5 C4 C3 . . 133.4(3) ?
C9 C4 C3 . . 106.9(2) ?
C6 C5 C4 . . 119.2(3) ?
C6 C5 H5 . . 120.4 ?
C4 C5 H5 . . 120.4 ?
C5 C6 C7 . . 120.9(3) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C6 C7 C8 . . 121.5(3) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C7 C8 C9 . . 117.7(3) ?
C7 C8 H8 . . 121.2 ?
C9 C8 H8 . . 121.2 ?
C8 C9 C4 . . 121.0(3) ?
C8 C9 N1 . . 131.1(3) ?
C4 C9 N1 . . 107.8(2) ?
C11 C10 C15 . . 119.5(3) ?
C11 C10 S1 . . 120.4(3) ?
C15 C10 S1 . . 120.1(3) ?
C10 C11 C12 . . 119.5(4) ?
C10 C11 H11 . . 120.2 ?
C12 C11 H11 . . 120.2 ?
C13 C12 C11 . . 120.3(4) ?
C13 C12 H12 . . 119.8 ?
C11 C12 H12 . . 119.8 ?
C14 C13 C12 . . 120.7(4) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C15 . . 120.0(4) ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C14 C15 C10 . . 120.0(4) ?
C14 C15 H15 . . 120.0 ?
C10 C15 H15 . . 120.0 ?
C21 C16 C17 . . 118.8(3) ?
C21 C16 S2 . . 124.6(2) ?
C17 C16 S2 . . 116.5(2) ?
C18 C17 C16 . . 120.2(3) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C19 C18 C17 . . 121.4(3) ?
C19 C18 H18 . . 119.3 ?
C17 C18 H18 . . 119.3 ?
C18 C19 C20 . . 119.7(3) ?
C18 C19 H19 . . 120.1 ?
C20 C19 H19 . . 120.1 ?
C19 C20 C21 . . 119.7(3) ?
C19 C20 H20 . . 120.2 ?
C21 C20 H20 . . 120.2 ?
C16 C21 C20 . . 120.2(3) ?
C16 C21 H21 . . 119.9 ?
C20 C21 H21 . . 119.9 ?
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
S1 O2 . 1.417(2) ?
S1 O1 . 1.425(2) ?
S1 N1 . 1.671(2) ?
S1 C10 . 1.758(3) ?
S2 C3 . 1.754(3) y
S2 C16 . 1.774(3) y
N1 C9 . 1.423(3) y
N1 C2 . 1.442(3) y
C1 C2 . 1.490(3) ?
C1 C1 3_565 1.542(5) ?
C1 H1A . .9700 ?
C1 H1B . .9700 ?
C2 C3 . 1.349(3) ?
C3 C4 . 1.438(4) ?
C4 C5 . 1.384(4) ?
C4 C9 . 1.397(4) ?
C5 C6 . 1.371(5) ?
C5 H5 . .9300 ?
C6 C7 . 1.375(5) ?
C6 H6 . .9300 ?
C7 C8 . 1.378(5) ?
C7 H7 . .9300 ?
C8 C9 . 1.391(4) ?
C8 H8 . .9300 ?
C10 C11 . 1.365(4) ?
C10 C15 . 1.380(5) ?
C11 C12 . 1.384(5) ?
C11 H11 . .9300 ?
C12 C13 . 1.349(5) ?
C12 H12 . .9300 ?
C13 C14 . 1.352(5) ?
C13 H13 . .9300 ?
C14 C15 . 1.374(5) ?
C14 H14 . .9300 ?
C15 H15 . .9300 ?
C16 C21 . 1.378(4) ?
C16 C17 . 1.389(4) ?
C17 C18 . 1.357(4) ?
C17 H17 . .9300 ?
C18 C19 . 1.353(5) ?
C18 H18 . .9300 ?
C19 C20 . 1.379(5) ?
C19 H19 . .9300 ?
C20 C21 . 1.384(4) ?
C20 H20 . .9300 ?
C21 H21 . .9300 ?
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
_geom_hbond_publ_flag
C1 H1A S2 1_555 .97 2.85 3.292(3) 109 y
C1 H1B O2 1_555 .97 2.30 2.857(3) 115 y
C8 H8 O1 1_555 .93 2.41 2.985(4) 120 y
C11 H11 O1 1_555 .93 2.54 2.913(4) 105 y
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
_geom_torsion_publ_flag
O2 S1 N1 C9 . -179.1(2) ?
O1 S1 N1 C9 . -50.1(2) ?
C10 S1 N1 C9 . 64.7(2) y
O2 S1 N1 C2 . 36.7(2) ?
O1 S1 N1 C2 . 165.7(2) ?
C10 S1 N1 C2 . -79.5(2) y
C9 N1 C2 C3 . 2.2(3) y
S1 N1 C2 C3 . 150.3(2) y
C9 N1 C2 C1 . 175.1(2) ?
S1 N1 C2 C1 . -36.8(3) y
C1 C1 C2 C3 3_565 102.7(3) ?
C1 C1 C2 N1 3_565 -68.7(4) ?
N1 C2 C3 C4 . -1.2(3) ?
C1 C2 C3 C4 . -173.7(2) ?
N1 C2 C3 S2 . 175.1(2) y
C1 C2 C3 S2 . 2.5(4) ?
C16 S2 C3 C2 . 119.5(3) ?
C16 S2 C3 C4 . -64.8(3) ?
C2 C3 C4 C5 . 179.5(3) ?
S2 C3 C4 C5 . 3.2(5) ?
C2 C3 C4 C9 . -.3(3) ?
S2 C3 C4 C9 . -176.6(2) ?
C9 C4 C5 C6 . -.7(5) ?
C3 C4 C5 C6 . 179.5(3) ?
C4 C5 C6 C7 . .0(6) ?
C5 C6 C7 C8 . .0(6) ?
C6 C7 C8 C9 . .7(5) ?
C7 C8 C9 C4 . -1.3(4) ?
C7 C8 C9 N1 . 178.0(3) ?
C5 C4 C9 C8 . 1.4(4) ?
C3 C4 C9 C8 . -178.8(3) ?
C5 C4 C9 N1 . -178.1(3) ?
C3 C4 C9 N1 . 1.8(3) ?
C2 N1 C9 C8 . 178.1(3) ?
S1 N1 C9 C8 . 28.8(4) y
C2 N1 C9 C4 . -2.5(3) ?
S1 N1 C9 C4 . -151.8(2) y
O2 S1 C10 C11 . 135.7(3) y
O1 S1 C10 C11 . 2.4(3) ?
N1 S1 C10 C11 . -110.5(3) ?
O2 S1 C10 C15 . -47.8(3) ?
O1 S1 C10 C15 . 178.9(3) ?
N1 S1 C10 C15 . 66.0(3) ?
C15 C10 C11 C12 . 2.8(6) ?
S1 C10 C11 C12 . 179.3(3) ?
C10 C11 C12 C13 . -3.2(7) ?
C11 C12 C13 C14 . 1.0(7) ?
C12 C13 C14 C15 . 1.6(7) ?
C13 C14 C15 C10 . -1.9(7) ?
C11 C10 C15 C14 . -.3(6) ?
S1 C10 C15 C14 . -176.8(3) ?
C3 S2 C16 C21 . -23.4(3) ?
C3 S2 C16 C17 . 158.2(2) ?
C21 C16 C17 C18 . .4(5) ?
S2 C16 C17 C18 . 178.9(3) ?
C16 C17 C18 C19 . .7(5) ?
C17 C18 C19 C20 . -.7(6) ?
C18 C19 C20 C21 . -.4(5) ?
C17 C16 C21 C20 . -1.5(5) ?
S2 C16 C21 C20 . -179.9(2) ?
C19 C20 C21 C16 . 1.5(5) ?
