#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/34/2233461.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_2233461
loop_
_publ_author_name
'Al-Najjar, Belal O.'
'Tengku Muhammad, Tengku Sifzizul'
'Wahab, Habibah A.'
'Rosli, Mohd Mustaqim'
'Fun, Hoong-Kun'
_publ_section_title
;
 4-(3-Methylbenzenesulfonamido)phenyl 3-methylbenzenesulfonate
;
_journal_coeditor_code           HB6544
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o258
_journal_paper_doi               10.1107/S1600536811054808
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C20 H19 N O5 S2'
_chemical_formula_moiety         'C20 H19 N O5 S2'
_chemical_formula_sum            'C20 H19 N O5 S2'
_chemical_formula_weight         417.48
_chemical_name_systematic
;
4-(3-Methylbenzenesulfonamido)phenyl 3-methylbenzenesulfonate
;
_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                 109.7000(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.43520(10)
_cell_length_b                   9.12500(10)
_cell_length_c                   15.4402(2)
_cell_measurement_reflns_used    9887
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      32.79
_cell_measurement_theta_min      2.69
_cell_volume                     1914.76(4)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART 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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21937
_diffrn_reflns_theta_full        32.95
_diffrn_reflns_theta_max         32.95
_diffrn_reflns_theta_min         2.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  0.9255
_exptl_absorpt_correction_T_min  0.8831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.403
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0310
_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)+(0.0485P)²+1.0937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                3249
_reflns_number_total             3533
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6544.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2233461
_cod_database_fobs_code          2233461
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 0.261632(15) 0.38804(2) 0.813408(15) 0.01868(7) Uani d . 1 1
O O1 0.30077(5) 0.33201(8) 0.73257(5) 0.01910(13) Uani d P 0.50 1
N N1 0.30077(5) 0.33201(8) 0.73257(5) 0.01910(13) Uani d P 0.50 1
H H1 0.2719 0.2309 0.7120 0.023 Uiso d PR 0.50 1
O O2 0.15974(5) 0.34770(9) 0.78153(5) 0.02715(16) Uani d . 1 1
O O3 0.28871(6) 0.53930(8) 0.83108(6) 0.02607(15) Uani d . 1 1
C C1 0.43833(8) 0.12376(12) 1.06033(7) 0.02529(19) Uani d . 1 1
H H1A 0.4772 0.0678 1.1116 0.030 Uiso calc R 1 1
C C2 0.46090(8) 0.27063(12) 1.05424(7) 0.0268(2) Uani d . 1 1
H H2A 0.5145 0.3140 1.1012 0.032 Uiso calc R 1 1
C C3 0.40519(7) 0.35443(11) 0.97948(7) 0.02235(17) Uani d . 1 1
H H3A 0.4195 0.4552 0.9750 0.027 Uiso calc R 1 1
C C4 0.32808(6) 0.28698(9) 0.91157(6) 0.01695(15) Uani d . 1 1
C C5 0.30453(7) 0.14007(10) 0.91733(6) 0.01931(16) Uani d . 1 1
H H5A 0.2511 0.0969 0.8701 0.023 Uiso calc R 1 1
C C6 0.35980(8) 0.05647(10) 0.99286(7) 0.02188(17) Uani d . 1 1
C C7 0.33362(11) -0.10114(11) 1.00160(9) 0.0333(2) Uani d . 1 1
H H7A 0.3116 -0.1471 0.9407 0.050 Uiso calc R 1 1
H H7B 0.2807 -0.1058 1.0279 0.050 Uiso calc R 1 1
H H7C 0.3915 -0.1531 1.0419 0.050 Uiso calc R 1 1
C C8 0.40253(6) 0.33636(9) 0.74375(6) 0.01551(14) Uani d . 1 1
C C9 0.45112(6) 0.20366(9) 0.74745(6) 0.01958(16) Uani d . 1 1
H H9A 0.4176 0.1138 0.7465 0.023 Uiso calc R 1 1
C C12 0.45042(6) 0.46948(9) 0.74605(6) 0.01721(15) Uani d . 1 1
H H12A 0.4160 0.5593 0.7423 0.021 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
O2 S1 O3 . . 119.64(5)
O2 S1 O1 . . 103.82(4)
O3 S1 O1 . . 107.89(4)
O2 S1 C4 . . 111.11(4)
O3 S1 C4 . . 107.83(5)
O1 S1 C4 . . 105.59(4)
C8 O1 S1 . . 120.90(6)
C8 O1 H1 . . 111.2
S1 O1 H1 . . 108.3
C2 C1 C6 . . 121.55(9)
C2 C1 H1A . . 119.2
C6 C1 H1A . . 119.2
C1 C2 C3 . . 120.17(9)
C1 C2 H2A . . 119.9
C3 C2 H2A . . 119.9
C4 C3 C2 . . 118.32(9)
C4 C3 H3A . . 120.8
C2 C3 H3A . . 120.8
C3 C4 C5 . . 121.92(8)
C3 C4 S1 . . 118.94(7)
C5 C4 S1 . . 119.08(7)
C4 C5 C6 . . 119.72(9)
C4 C5 H5A . . 120.1
C6 C5 H5A . . 120.1
C1 C6 C5 . . 118.30(9)
C1 C6 C7 . . 121.23(9)
C5 C6 C7 . . 120.45(10)
C6 C7 H7A . . 109.5
C6 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C6 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
C9 C8 C12 . . 121.29(8)
C9 C8 O1 . . 117.85(7)
C12 C8 O1 . . 120.78(8)
C9 C9 C8 2_656 . 119.46(5)
C9 C9 H9A 2_656 . 120.3
C8 C9 H9A . . 120.3
C8 C12 C12 . 2_656 119.23(5)
C8 C12 H12A . . 120.4
C12 C12 H12A 2_656 . 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 O2 . 1.4329(8)
S1 O3 . 1.4354(8)
S1 O1 . 1.6167(7)
S1 C4 . 1.7572(9)
O1 C8 . 1.4206(10)
O1 H1 . 1.0188
C1 C2 . 1.3899(15)
C1 C6 . 1.3968(15)
C1 H1A . 0.9500
C2 C3 . 1.3922(14)
C2 H2A . 0.9500
C3 C4 . 1.3894(13)
C3 H3A . 0.9500
C4 C5 . 1.3931(12)
C5 C6 . 1.3969(13)
C5 H5A . 0.9500
C6 C7 . 1.5046(14)
C7 H7A . 0.9800
C7 H7B . 0.9800
C7 H7C . 0.9800
C8 C9 . 1.3909(12)
C8 C12 . 1.3921(12)
C9 C9 2_656 1.3866(18)
C9 H9A . 0.9500
C12 C12 2_656 1.3949(16)
C12 H12A . 0.9500
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
N1 H1 O3 4_546 1.02 1.97 2.9854(11) 178 yes
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
O2 S1 O1 C8 . -172.37(7)
O3 S1 O1 C8 . 59.70(8)
C4 S1 O1 C8 . -55.39(7)
C6 C1 C2 C3 . -0.35(16)
C1 C2 C3 C4 . -0.71(15)
C2 C3 C4 C5 . 1.11(14)
C2 C3 C4 S1 . -176.24(8)
O2 S1 C4 C3 . -144.83(8)
O3 S1 C4 C3 . -11.90(9)
O1 S1 C4 C3 . 103.24(8)
O2 S1 C4 C5 . 37.75(8)
O3 S1 C4 C5 . 170.68(7)
O1 S1 C4 C5 . -74.19(8)
C3 C4 C5 C6 . -0.44(13)
S1 C4 C5 C6 . 176.91(7)
C2 C1 C6 C5 . 1.03(15)
C2 C1 C6 C7 . -177.82(10)
C4 C5 C6 C1 . -0.63(14)
C4 C5 C6 C7 . 178.23(9)
S1 O1 C8 C9 . 113.82(8)
S1 O1 C8 C12 . -69.45(10)
C12 C8 C9 C9 2_656 -0.70(16)
O1 C8 C9 C9 2_656 176.01(10)
C9 C8 C12 C12 2_656 -1.20(15)
O1 C8 C12 C12 2_656 -177.81(10)
