#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/48/2214820.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_2214820
loop_
_publ_author_name
'B. Thimme Gowda'
'K. S. Babitha'
'Miroslav Tokarčík'
'Jozef Kožíšek'
'Hartmut Fuess'
_publ_section_title
;
 4,6-Dimethylbenzene-1,3-disulfonamide
;
_journal_coeditor_code           OM2140
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3361
_journal_page_last               o3361
_journal_paper_doi               10.1107/S1600536807031297
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H12 N2 O4 S2'
_chemical_formula_moiety         'C8 H12 N2 O4 S2'
_chemical_formula_sum            'C8 H12 N2 O4 S2'
_chemical_formula_weight         264.32
_chemical_name_systematic
;
4,6-Dimethylbenzene-1,3-disulfonamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4793(2)
_cell_length_b                   8.05200(10)
_cell_length_c                   19.1935(4)
_cell_measurement_reflns_used    14260
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      29.5292
_cell_measurement_theta_min      2.9959
_cell_volume                     2237.72(6)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002)
;
_computing_publication_material
;
SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33751
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         5.1
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.476
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(Clark & Reid, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.282
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2183
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0661P)²+0.0106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.096
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                1693
_reflns_number_total             2183
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om2140.cif
_cod_data_source_block           I
_cod_database_code               2214820
_cod_database_fobs_code          2214820
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
C C1 0.23215(12) 0.4353(2) 0.44644(10) 0.0325(4) Uani d . 1
C C2 0.32502(12) 0.4435(2) 0.42955(10) 0.0320(4) Uani d . 1
H H2 0.3683 0.4692 0.4637 0.038 Uiso calc R 1
C C3 0.35327(13) 0.4134(2) 0.36175(10) 0.0337(4) Uani d . 1
C C4 0.28991(14) 0.3696(2) 0.30997(11) 0.0421(5) Uani d . 1
C C5 0.19745(14) 0.3675(3) 0.32909(12) 0.0470(5) Uani d . 1
H H5 0.1541 0.342 0.295 0.056 Uiso calc R 1
C C6 0.16569(12) 0.4010(2) 0.39580(11) 0.0376(5) Uani d . 1
C C7 0.31541(17) 0.3244(3) 0.23612(12) 0.0656(7) Uani d . 1
H H7A 0.3575 0.2323 0.2366 0.098 Uiso calc R 1
H H7B 0.3443 0.4179 0.214 0.098 Uiso calc R 1
H H7C 0.2607 0.2943 0.2109 0.098 Uiso calc R 1
C C8 0.06333(14) 0.3980(3) 0.41059(13) 0.0535(6) Uani d . 1
H H8A 0.0466 0.4947 0.437 0.08 Uiso calc R 1
H H8B 0.0484 0.3001 0.4368 0.08 Uiso calc R 1
H H8C 0.0299 0.3972 0.3674 0.08 Uiso calc R 1
N N1 0.28772(11) 0.4730(2) 0.58211(9) 0.0397(4) Uani d D 1
H H1A 0.3209(14) 0.556(2) 0.5760(12) 0.048 Uiso d D 1
H H1B 0.3178(13) 0.387(2) 0.5829(12) 0.048 Uiso d D 1
N N2 0.51984(14) 0.2642(3) 0.33063(11) 0.0569(5) Uani d D 1
H H2A 0.5078(17) 0.213(3) 0.2941(11) 0.068 Uiso d D 1
H H2B 0.5402(18) 0.217(3) 0.3656(11) 0.068 Uiso d D 1
O O1 0.14493(9) 0.32605(15) 0.55488(7) 0.0451(4) Uani d . 1
O O2 0.15455(9) 0.62787(16) 0.53936(7) 0.0440(4) Uani d . 1
O O3 0.51437(10) 0.50240(18) 0.40649(8) 0.0507(4) Uani d . 1
O O4 0.48035(12) 0.5335(2) 0.28186(9) 0.0664(5) Uani d . 1
S S1 0.19779(3) 0.46871(5) 0.53417(2) 0.03266(18) Uani d . 1
S S2 0.47313(3) 0.43915(6) 0.34460(3) 0.03907(19) 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 0 '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 0.006 '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
C2 C1 C6 121.07(18)
C2 C1 S1 119.12(15)
C6 C1 S1 119.81(14)
C1 C2 C3 119.88(18)
C1 C2 H2 120.1
C3 C2 H2 120.1
C2 C3 C4 121.20(18)
C2 C3 S2 116.20(14)
C4 C3 S2 122.58(15)
C5 C4 C3 116.63(19)
C5 C4 C7 118.76(19)
C3 C4 C7 124.61(19)
C6 C5 C4 124.15(18)
C6 C5 H5 117.9
C4 C5 H5 117.9
C5 C6 C1 116.93(17)
C5 C6 C8 119.74(18)
C1 C6 C8 123.33(18)
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
S1 N1 H1A 114.1(16)
S1 N1 H1B 115.1(16)
H1A N1 H1B 112(2)
S2 N2 H2A 119.5(18)
S2 N2 H2B 114.9(19)
H2A N2 H2B 122(3)
O2 S1 O1 117.66(8)
O2 S1 N1 107.33(9)
O1 S1 N1 107.02(9)
O2 S1 C1 108.94(8)
O1 S1 C1 106.88(8)
N1 S1 C1 108.76(9)
O3 S2 O4 118.87(10)
O3 S2 N2 106.27(10)
O4 S2 N2 107.38(11)
O3 S2 C3 107.26(9)
O4 S2 C3 106.83(9)
N2 S2 C3 110.12(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.385(2)
C1 C6 1.395(3)
C1 S1 1.776(2)
C2 C3 1.386(3)
C2 H2 0.93
C3 C4 1.398(3)
C3 S2 1.7785(19)
C4 C5 1.388(3)
C4 C7 1.509(3)
C5 C6 1.387(3)
C5 H5 0.93
C6 C8 1.509(3)
C7 H7A 0.96
C7 H7B 0.96
C7 H7C 0.96
C8 H8A 0.96
C8 H8B 0.96
C8 H8C 0.96
N1 S1 1.5949(18)
N1 H1A 0.829(15)
N1 H1B 0.821(15)
N2 S2 1.586(2)
N2 H2A 0.830(17)
N2 H2B 0.825(17)
O1 S1 1.4364(13)
O2 S1 1.4297(13)
O3 S2 1.4236(15)
O4 S2 1.4275(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
N1 H1A O1 8_665 0.829(15) 2.269(16) 3.050(2) 157(2)
N1 H1B O2 8_655 0.821(15) 2.279(17) 3.016(2) 149(2)
N2 H2A O4 3_645 0.830(17) 2.062(19) 2.848(3) 158(2)
N2 H2B O1 4_556 0.825(17) 2.18(2) 2.939(2) 153(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
C6 C1 C2 C3 -1.6(3)
S1 C1 C2 C3 178.28(12)
C1 C2 C3 C4 -1.9(3)
C1 C2 C3 S2 176.44(12)
C2 C3 C4 C5 3.6(3)
S2 C3 C4 C5 -174.66(15)
C2 C3 C4 C7 -176.00(19)
S2 C3 C4 C7 5.7(3)
C3 C4 C5 C6 -1.9(3)
C7 C4 C5 C6 177.7(2)
C4 C5 C6 C1 -1.4(3)
C4 C5 C6 C8 179.01(19)
C2 C1 C6 C5 3.2(3)
S1 C1 C6 C5 -176.68(14)
C2 C1 C6 C8 -177.22(18)
S1 C1 C6 C8 2.9(3)
C2 C1 S1 O2 106.92(14)
C6 C1 S1 O2 -73.16(15)
C2 C1 S1 O1 -124.98(14)
C6 C1 S1 O1 54.94(16)
C2 C1 S1 N1 -9.76(16)
C6 C1 S1 N1 170.16(15)
C2 C3 S2 O3 -5.20(16)
C4 C3 S2 O3 173.16(16)
C2 C3 S2 O4 -133.67(15)
C4 C3 S2 O4 44.69(19)
C2 C3 S2 N2 110.03(16)
C4 C3 S2 N2 -71.62(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 482784
