##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Bis(4-methylphenylsulfonyl)amino 4-methylbenzenesulfonate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H21 N  O7 S3'
_chemical_formula_sum     'C21 H21 N  O7 S3'
_chemical_formula_iupac     'C21 H21 N  O7 S3'
_chemical_formula_weight     495.57
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     14.6523(6)
_cell_length_b     9.9342(5)
_cell_length_c     16.0953(6)
_cell_angle_alpha     90.00
_cell_angle_beta     99.355(4)
_cell_angle_gamma     90.00
_cell_volume     2311.65(17)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4103
_cell_measurement_theta_min     3.7278
_cell_measurement_theta_max     28.7734
_cell_measurement_temperature     295(2)
_exptl_crystal_description     prisms
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.424
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1032
_exptl_absorpt_coefficient_mu     0.363
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_absorpt_correction_T_min     0.945
_exptl_absorpt_correction_T_max     0.952
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Gemini CCD S Ultra'
_diffrn_measurement_method     'ω scans, thick slices'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15723
_diffrn_reflns_av_R_equivalents     0.0681
_diffrn_reflns_av_sigmaI/netI     0.0890
_diffrn_reflns_theta_min     3.74
_diffrn_reflns_theta_max     28.84
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.891
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_reflns_number_total     5389
_reflns_number_gt     2771
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1308
_refine_ls_R_factor_gt     0.0524
_refine_ls_wR_factor_gt     0.0837
_refine_ls_wR_factor_ref     0.1021
_refine_ls_goodness_of_fit_ref     0.993
_refine_ls_restrained_S_all     0.993
_refine_ls_number_reflns     5389
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0356P)²+0.4860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.276
_refine_diff_density_min     -0.202
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'S' 'S' 0.1246 0.1234
                         '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'
_computing_data_collection     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_cell_refinement     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                            'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.64217(5) 1.05279(8) 0.84217(4) 0.0590(2) Uani d . 1 1 . .
    S S2 0.70071(5) 1.03700(7) 1.03406(4) 0.05370(19) Uani d . 1 1 . .
    S S3 0.88243(5) 1.17019(8) 0.92356(4) 0.0583(2) Uani d . 1 1 . .
    O O11 0.68307(14) 1.1219(2) 0.78017(11) 0.0757(6) Uani d . 1 1 . .
    O O21 0.55578(12) 1.0922(2) 0.86219(12) 0.0747(6) Uani d . 1 1 . .
    O O12 0.61333(12) 1.09443(18) 1.04105(11) 0.0644(5) Uani d . 1 1 . .
    O O22 0.78335(12) 1.08180(19) 1.08539(11) 0.0666(5) Uani d . 1 1 . .
    O O13 0.83000(14) 1.29006(19) 0.91856(12) 0.0741(6) Uani d . 1 1 . .
    O O23 0.95277(12) 1.1446(2) 0.99318(11) 0.0763(6) Uani d . 1 1 . .
    N N1 0.71880(13) 1.0808(2) 0.93407(12) 0.0516(5) Uani d . 1 1 . .
    C C11 0.64351(18) 0.8815(3) 0.82238(15) 0.0535(7) Uani d . 1 1 . .
    C C21 0.5743(2) 0.8003(3) 0.84448(16) 0.0642(8) Uani d . 1 1 . .
    H H21 0.5266 0.8371 0.8689 0.077 Uiso calc R 1 1 . .
    C C31 0.5776(2) 0.6633(4) 0.82941(18) 0.0760(9) Uani d . 1 1 . .
    H H31 0.5314 0.6079 0.8437 0.091 Uiso calc R 1 1 . .
    C C41 0.6481(3) 0.6076(4) 0.79354(19) 0.0793(10) Uani d . 1 1 . .
    C C51 0.7144(2) 0.6914(4) 0.77068(19) 0.0790(10) Uani d . 1 1 . .
    H H51 0.7611 0.6548 0.7449 0.095 Uiso calc R 1 1 . .
    C C61 0.7136(2) 0.8264(3) 0.78470(16) 0.0692(8) Uani d . 1 1 . .
    H H61 0.7596 0.8811 0.7692 0.083 Uiso calc R 1 1 . .
    C C71 0.6501(3) 0.4576(4) 0.7794(2) 0.1166(14) Uani d . 1 1 . .
    H H71A 0.6454 0.4396 0.7202 0.175 Uiso calc R 1 1 . .
    H H71B 0.5991 0.4163 0.8003 0.175 Uiso calc R 1 1 . .
    H H71C 0.7072 0.4214 0.8086 0.175 Uiso calc R 1 1 . .
    C C12 0.69481(17) 0.8623(3) 1.03894(14) 0.0481(6) Uani d . 1 1 . .
    C C22 0.61244(19) 0.8027(3) 1.05039(15) 0.0580(7) Uani d . 1 1 . .
    H H22 0.5605 0.8551 1.0534 0.070 Uiso calc R 1 1 . .
    C C32 0.6082(2) 0.6651(3) 1.05717(16) 0.0668(8) Uani d . 1 1 . .
    H H32 0.5531 0.6255 1.0661 0.080 Uiso calc R 1 1 . .
    C C42 0.6830(2) 0.5841(3) 1.05120(16) 0.0646(8) Uani d . 1 1 . .
    C C52 0.7645(2) 0.6458(3) 1.03959(18) 0.0725(9) Uani d . 1 1 . .
    H H52 0.8159 0.5927 1.0354 0.087 Uiso calc R 1 1 . .
    C C62 0.77195(18) 0.7825(3) 1.03406(17) 0.0655(8) Uani d . 1 1 . .
    H H62 0.8278 0.8218 1.0271 0.079 Uiso calc R 1 1 . .
    C C72 0.6760(2) 0.4331(3) 1.0568(2) 0.0937(11) Uani d . 1 1 . .
    H H72A 0.6706 0.4079 1.1134 0.141 Uiso calc R 1 1 . .
    H H72B 0.7305 0.3927 1.0416 0.141 Uiso calc R 1 1 . .
    H H72C 0.6225 0.4026 1.0191 0.141 Uiso calc R 1 1 . .
    C C13 0.92562(17) 1.1392(3) 0.83080(15) 0.0509(6) Uani d . 1 1 . .
    C C23 0.88491(19) 1.1969(3) 0.75569(17) 0.0638(8) Uani d . 1 1 . .
    H H23 0.8313 1.2479 0.7531 0.077 Uiso calc R 1 1 . .
    C C33 0.9245(2) 1.1781(3) 0.68498(16) 0.0684(8) Uani d . 1 1 . .
    H H33 0.8978 1.2184 0.6347 0.082 Uiso calc R 1 1 . .
    C C43 1.0027(2) 1.1010(3) 0.68671(17) 0.0644(8) Uani d . 1 1 . .
    C C53 1.04090(19) 1.0425(3) 0.76170(17) 0.0686(8) Uani d . 1 1 . .
    H H53 1.0935 0.9894 0.7637 0.082 Uiso calc R 1 1 . .
    C C63 1.00350(18) 1.0603(3) 0.83377(16) 0.0608(7) Uani d . 1 1 . .
    H H63 1.0303 1.0198 0.8839 0.073 Uiso calc R 1 1 . .
    C C73 1.0461(2) 1.0825(4) 0.60865(18) 0.1033(13) Uani d . 1 1 . .
    H H73A 1.0743 1.1654 0.5955 0.155 Uiso calc R 1 1 . .
    H H73B 0.9994 1.0570 0.5624 0.155 Uiso calc R 1 1 . .
    H H73C 1.0924 1.0133 0.6184 0.155 Uiso calc R 1 1 . .
    O O33 0.80876(11) 1.04082(17) 0.92177(10) 0.0543(4) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 O21 . 1.4115(19) ?
    S1 O11 . 1.4214(19) ?
    S1 N1 . 1.728(2) ?
    S1 C11 . 1.732(3) ?
    S2 O22 . 1.4218(18) ?
    S2 O12 . 1.4228(17) ?
    S2 N1 . 1.729(2) ?
    S2 C12 . 1.740(3) ?
    S3 O13 . 1.412(2) ?
    S3 O23 . 1.4167(19) ?
    S3 O33 . 1.6756(18) ?
    S3 C13 . 1.741(2) ?
    N1 O33 . 1.421(2) ?
    C11 C21 . 1.387(4) ?
    C11 C61 . 1.388(4) ?
    C21 C31 . 1.385(4) ?
    C21 H21 . 0.9300 ?
    C31 C41 . 1.379(4) ?
    C31 H31 . 0.9300 ?
    C41 C51 . 1.375(5) ?
    C41 C71 . 1.508(5) ?
    C51 C61 . 1.360(4) ?
    C51 H51 . 0.9300 ?
    C61 H61 . 0.9300 ?
    C71 H71A . 0.9600 ?
    C71 H71B . 0.9600 ?
    C71 H71C . 0.9600 ?
    C12 C22 . 1.383(3) ?
    C12 C62 . 1.393(3) ?
    C22 C32 . 1.373(4) ?
    C22 H22 . 0.9300 ?
    C32 C42 . 1.376(4) ?
    C32 H32 . 0.9300 ?
    C42 C52 . 1.382(4) ?
    C42 C72 . 1.507(4) ?
    C52 C62 . 1.367(4) ?
    C52 H52 . 0.9300 ?
    C62 H62 . 0.9300 ?
    C72 H72A . 0.9600 ?
    C72 H72B . 0.9600 ?
    C72 H72C . 0.9600 ?
    C13 C63 . 1.379(3) ?
    C13 C23 . 1.383(3) ?
    C23 C33 . 1.371(4) ?
    C23 H23 . 0.9300 ?
    C33 C43 . 1.376(4) ?
    C33 H33 . 0.9300 ?
    C43 C53 . 1.374(4) ?
    C43 C73 . 1.509(4) ?
    C53 C63 . 1.372(3) ?
    C53 H53 . 0.9300 ?
    C63 H63 . 0.9300 ?
    C73 H73A . 0.9600 ?
    C73 H73B . 0.9600 ?
    C73 H73C . 0.9600 ?
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
    O21 S1 O11 . . 121.48(13) ?
    O21 S1 N1 . . 104.00(11) ?
    O11 S1 N1 . . 103.52(11) ?
    O21 S1 C11 . . 110.62(13) ?
    O11 S1 C11 . . 109.07(13) ?
    N1 S1 C11 . . 106.88(11) ?
    O22 S2 O12 . . 121.39(11) ?
    O22 S2 N1 . . 102.55(10) ?
    O12 S2 N1 . . 104.41(10) ?
    O22 S2 C12 . . 109.26(12) ?
    O12 S2 C12 . . 110.14(12) ?
    N1 S2 C12 . . 108.01(11) ?
    O13 S3 O23 . . 121.02(13) ?
    O13 S3 O33 . . 107.63(10) ?
    O23 S3 O33 . . 105.06(11) ?
    O13 S3 C13 . . 111.73(12) ?
    O23 S3 C13 . . 109.12(12) ?
    O33 S3 C13 . . 99.95(10) ?
    O33 N1 S1 . . 108.91(14) ?
    O33 N1 S2 . . 110.21(14) ?
    S1 N1 S2 . . 125.43(12) ?
    C21 C11 C61 . . 120.5(3) ?
    C21 C11 S1 . . 119.6(2) ?
    C61 C11 S1 . . 119.9(2) ?
    C31 C21 C11 . . 118.6(3) ?
    C31 C21 H21 . . 120.7 ?
    C11 C21 H21 . . 120.7 ?
    C41 C31 C21 . . 121.2(3) ?
    C41 C31 H31 . . 119.4 ?
    C21 C31 H31 . . 119.4 ?
    C51 C41 C31 . . 118.6(3) ?
    C51 C41 C71 . . 121.7(4) ?
    C31 C41 C71 . . 119.7(4) ?
    C61 C51 C41 . . 121.9(3) ?
    C61 C51 H51 . . 119.1 ?
    C41 C51 H51 . . 119.1 ?
    C51 C61 C11 . . 119.2(3) ?
    C51 C61 H61 . . 120.4 ?
    C11 C61 H61 . . 120.4 ?
    C41 C71 H71A . . 109.5 ?
    C41 C71 H71B . . 109.5 ?
    H71A C71 H71B . . 109.5 ?
    C41 C71 H71C . . 109.5 ?
    H71A C71 H71C . . 109.5 ?
    H71B C71 H71C . . 109.5 ?
    C22 C12 C62 . . 119.8(3) ?
    C22 C12 S2 . . 118.9(2) ?
    C62 C12 S2 . . 121.2(2) ?
    C32 C22 C12 . . 119.2(3) ?
    C32 C22 H22 . . 120.4 ?
    C12 C22 H22 . . 120.4 ?
    C22 C32 C42 . . 122.0(3) ?
    C22 C32 H32 . . 119.0 ?
    C42 C32 H32 . . 119.0 ?
    C32 C42 C52 . . 117.8(3) ?
    C32 C42 C72 . . 121.0(3) ?
    C52 C42 C72 . . 121.2(3) ?
    C62 C52 C42 . . 122.0(3) ?
    C62 C52 H52 . . 119.0 ?
    C42 C52 H52 . . 119.0 ?
    C52 C62 C12 . . 119.2(3) ?
    C52 C62 H62 . . 120.4 ?
    C12 C62 H62 . . 120.4 ?
    C42 C72 H72A . . 109.5 ?
    C42 C72 H72B . . 109.5 ?
    H72A C72 H72B . . 109.5 ?
    C42 C72 H72C . . 109.5 ?
    H72A C72 H72C . . 109.5 ?
    H72B C72 H72C . . 109.5 ?
    C63 C13 C23 . . 120.2(2) ?
    C63 C13 S3 . . 119.0(2) ?
    C23 C13 S3 . . 120.8(2) ?
    C33 C23 C13 . . 119.3(2) ?
    C33 C23 H23 . . 120.4 ?
    C13 C23 H23 . . 120.4 ?
    C23 C33 C43 . . 121.5(2) ?
    C23 C33 H33 . . 119.3 ?
    C43 C33 H33 . . 119.3 ?
    C53 C43 C33 . . 118.2(3) ?
    C53 C43 C73 . . 120.9(3) ?
    C33 C43 C73 . . 120.9(3) ?
    C63 C53 C43 . . 121.8(3) ?
    C63 C53 H53 . . 119.1 ?
    C43 C53 H53 . . 119.1 ?
    C53 C63 C13 . . 119.1(2) ?
    C53 C63 H63 . . 120.5 ?
    C13 C63 H63 . . 120.5 ?
    C43 C73 H73A . . 109.5 ?
    C43 C73 H73B . . 109.5 ?
    H73A C73 H73B . . 109.5 ?
    C43 C73 H73C . . 109.5 ?
    H73A C73 H73C . . 109.5 ?
    H73B C73 H73C . . 109.5 ?
    N1 O33 S3 . . 113.13(14) ?
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
    C22 H22 O21 3_677 0.93 2.40 3.205(3) 144.4
    C63 H63 O23 3_777 0.93 2.55 3.425(3) 157.8
data_global
_journal_date_recd_electronic     2012-07-20
_journal_date_accepted     2012-09-09
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2012
_journal_volume     68
_journal_issue     10
_journal_page_first     o417
_journal_page_last     o420
_journal_paper_category     FO
_journal_paper_doi     10.1107/S0108270112039182
_journal_coeditor_code     DT3015
_publ_contact_author
;
Sebastián Suarez
Departamento de Química Inorgánica, Analítica y Química
Física/INQUIMAE--CONICET,
Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires
Buenos Aires
Argentina
;
_publ_contact_author_email     seba@qi.fcen.uba.ar
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Bis(4-methylphenylsulfonyl)amino 4-methylbenzenesulfonate: a new member of the
(RSO₂)ON(SO₂R)₂ family
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Suarez, Sebastián' .
;
Departamento de Química Inorgánica, Analítica y Química Física
INQUIMAE-CONICET
Facultad de Ciencias Exactas y Naturales
Universidad de Buenos Aires
Buenos Aires
Argentina
;
    'Doctorovich, Fabio'
;
Author to whom enquires should be addressed, e-mail: doctorovich@qi.fcen.uba.ar.
;
;
Departamento de Química Inorgánica, Analítica y Química Física
INQUIMAE-CONICET
Facultad de Ciencias Exactas y Naturales
Universidad de Buenos Aires
Buenos Aires
Argentina
;
    'Baggio, Ricardo' .
;
Gerencia de Investigación y Aplicaciones
Centro Atómico Constituyentes
Comisión Nacional de Energía Atómica
Buenos Aires
Argentina
;
