##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
N,N-Dimethyl-1-phenylsulfonyl-1H-pyrrole-3-sulfonamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H14 N2 O4 S2'
_chemical_formula_sum     'C12 H14 N2 O4 S2'
_chemical_formula_iupac     'C12 H14 N2 O4 S2'
_chemical_formula_weight     314.37
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     8.1322(7)
_cell_length_b     11.1027(9)
_cell_length_c     16.0757(14)
_cell_angle_alpha     90.00
_cell_angle_beta     100.680(2)
_cell_angle_gamma     90.00
_cell_volume     1426.3(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5103
_cell_measurement_theta_min     2.24
_cell_measurement_theta_max     28.28
_cell_measurement_temperature     173(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.26
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.464
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     656
_exptl_absorpt_coefficient_mu     0.387
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS in SAINT-Plus; Bruker, 2003)'
_exptl_absorpt_correction_T_min     0.7544
_exptl_absorpt_correction_T_max     0.92
_exptl_special_details
;
;
_diffrn_ambient_temperature     173(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     'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     15246
_diffrn_reflns_av_R_equivalents     0.0285
_diffrn_reflns_av_sigmaI/netI     0.0241
_diffrn_reflns_theta_min     2.24
_diffrn_reflns_theta_max     28.25
_diffrn_reflns_theta_full     28.25
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3534
_reflns_number_gt     3357
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0497
_refine_ls_R_factor_gt     0.0469
_refine_ls_wR_factor_gt     0.1069
_refine_ls_wR_factor_ref     0.1086
_refine_ls_goodness_of_fit_ref     1.198
_refine_ls_restrained_S_all     1.198
_refine_ls_number_reflns     3534
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0424P)²+1.2568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.515
_refine_diff_density_min     -0.301
_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'
    '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'
_computing_data_collection     'SMART (Bruker, 2002)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2003)'
_computing_data_reduction     'SAINT-Plus'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEX (McArdle, 1995)'
_computing_publication_material
                                'OSCAIL (McArdle, 1995) and PLATON (Spek, 2003)'
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
    S S1 0.76003(6) 0.14377(4) 0.06525(3) 0.01749(13) Uani d . 1 . .
    S S2 1.12146(6) 0.53927(4) 0.18637(3) 0.01793(13) Uani d . 1 . .
    O O1 0.74294(18) 0.04472(13) 0.11930(9) 0.0236(3) Uani d . 1 . .
    O O3 1.12617(18) 0.57871(13) 0.10194(9) 0.0242(3) Uani d . 1 . .
    O O4 1.07297(19) 0.62177(13) 0.24590(10) 0.0267(3) Uani d . 1 . .
    N N1 0.8467(2) 0.25417(15) 0.13011(10) 0.0180(3) Uani d . 1 . .
    O O2 0.86055(17) 0.13591(14) 0.00161(9) 0.0242(3) Uani d . 1 . .
    N N2 1.3090(2) 0.49114(15) 0.22630(10) 0.0203(3) Uani d . 1 . .
    C C8 0.5610(2) 0.19798(18) 0.02032(12) 0.0181(4) Uani d . 1 . .
    C C3 0.9852(2) 0.41716(17) 0.17857(12) 0.0174(4) Uani d . 1 . .
    C C9 0.4222(2) 0.14403(19) 0.04319(13) 0.0215(4) Uani d . 1 . .
    C C5 0.8208(2) 0.27053(19) 0.21248(12) 0.0213(4) Uani d . 1 . .
    C C2 0.9465(2) 0.34516(17) 0.10874(12) 0.0180(4) Uani d . 1 . .
    C C4 0.9060(3) 0.37005(19) 0.24382(13) 0.0215(4) Uani d . 1 . .
    C C12 0.3880(3) 0.3310(2) -0.07406(14) 0.0309(5) Uani d . 1 . .
    C C11 0.2481(3) 0.2764(2) -0.05285(14) 0.0285(5) Uani d . 1 . .
    C C10 0.2645(3) 0.1832(2) 0.00492(15) 0.0260(4) Uani d . 1 . .
    C C6 1.3342(3) 0.4506(2) 0.31501(14) 0.0301(5) Uani d . 1 . .
    C C13 0.5469(3) 0.2912(2) -0.03821(13) 0.0254(4) Uani d . 1 . .
    C C7 1.3836(3) 0.4085(2) 0.17229(15) 0.0275(5) Uani d . 1 . .
    H H4 0.909(3) 0.401(2) 0.2954(15) 0.023(6) Uiso d . 1 . .
    H H7B 1.360(3) 0.435(2) 0.1139(16) 0.023(6) Uiso d . 1 . .
    H H2 0.974(3) 0.351(2) 0.0543(16) 0.022(6) Uiso d . 1 . .
    H H9 0.439(3) 0.086(2) 0.0823(16) 0.026(6) Uiso d . 1 . .
    H H5 0.749(3) 0.216(2) 0.2350(15) 0.025(6) Uiso d . 1 . .
    H H10 0.169(3) 0.148(2) 0.0193(17) 0.032(7) Uiso d . 1 . .
    H H13 0.637(4) 0.324(2) -0.0526(17) 0.034(7) Uiso d . 1 . .
    H H6B 1.292(3) 0.511(3) 0.3475(17) 0.032(7) Uiso d . 1 . .
    H H6A 1.278(4) 0.373(3) 0.3226(18) 0.042(8) Uiso d . 1 . .
    H H7C 1.502(4) 0.407(3) 0.1948(18) 0.044(8) Uiso d . 1 . .
    H H7A 1.337(3) 0.326(3) 0.1725(17) 0.033(7) Uiso d . 1 . .
    H H11 0.142(4) 0.302(3) -0.0781(17) 0.036(7) Uiso d . 1 . .
    H H12 0.374(4) 0.398(3) -0.1135(19) 0.043(8) Uiso d . 1 . .
    H H6C 1.450(4) 0.442(3) 0.3323(17) 0.036(7) Uiso d . 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
 Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)
  6.1806 (0.0054) x - 6.1783 (0.0093) y + 3.0396 (0.0162) z = 4.0526 (0.0072)
 *    0.0058 (0.0012)  N1
 *   -0.0047 (0.0012)  C2
 *    0.0018 (0.0012)  C3
 *    0.0018 (0.0013)  C4
 *   -0.0047 (0.0012)  C5
 Rms deviation of fitted atoms =   0.0041
 - 0.9721 (0.0071) x + 7.3615 (0.0076) y + 12.0299 (0.0098) z = 1.1592 (0.0038)
 Angle to previous plane (with approximate esd) = 77.78 ( 0.07 )
 *   -0.0027 (0.0014)  C8
 *    0.0102 (0.0014)  C9
 *   -0.0082 (0.0015)  C10
 *   -0.0015 (0.0016)  C11
 *    0.0091 (0.0017)  C12
 *   -0.0069 (0.0016)  C13
 Rms deviation of fitted atoms =   0.0072
;
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 O1 . 1.4243(15) y
    S1 O2 . 1.4255(14) y
    S1 N1 . 1.6775(16) y
    S1 C8 . 1.7524(19) y
    S2 O4 . 1.4318(15) y
    S2 O3 . 1.4335(15) y
    S2 N2 . 1.6309(17) y
    S2 C3 . 1.7409(19) y
    N1 C2 . 1.378(2) y
    N1 C5 . 1.391(2) y
    N2 C7 . 1.470(3) y
    N2 C6 . 1.473(3) y
    C8 C9 . 1.386(3) n
    C8 C13 . 1.389(3) n
    C3 C2 . 1.366(3) y
    C3 C4 . 1.428(3) y
    C9 C10 . 1.386(3) n
    C9 H9 . 0.90(3) n
    C5 C4 . 1.351(3) y
    C5 H5 . 0.96(3) n
    C2 H2 . 0.94(2) n
    C4 H4 . 0.90(2) n
    C12 C13 . 1.386(3) n
    C12 C11 . 1.386(3) n
    C12 H12 . 0.97(3) n
    C11 C10 . 1.380(3) n
    C11 H11 . 0.93(3) n
    C10 H10 . 0.94(3) n
    C6 H6B . 0.95(3) n
    C6 H6A . 1.00(3) n
    C6 H6C . 0.94(3) n
    C13 H13 . 0.89(3) n
    C7 H7B . 0.97(2) n
    C7 H7C . 0.96(3) n
    C7 H7A . 0.99(3) n
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
    O1 S1 O2 . . 121.63(9) y
    O1 S1 N1 . . 105.21(8) y
    O2 S1 N1 . . 105.07(8) y
    O1 S1 C8 . . 109.24(9) y
    O2 S1 C8 . . 109.51(9) y
    N1 S1 C8 . . 104.77(9) y
    O4 S2 O3 . . 119.76(9) y
    O4 S2 N2 . . 107.45(9) y
    O3 S2 N2 . . 106.59(9) y
    O4 S2 C3 . . 107.21(9) y
    O3 S2 C3 . . 107.34(9) y
    N2 S2 C3 . . 108.03(9) y
    C2 N1 C5 . . 109.96(16) y
    C2 N1 S1 . . 125.42(13) y
    C5 N1 S1 . . 124.53(14) y
    C7 N2 C6 . . 112.49(18) y
    C7 N2 S2 . . 115.50(14) y
    C6 N2 S2 . . 115.69(14) y
    C9 C8 C13 . . 122.18(18) y
    C9 C8 S1 . . 118.52(15) y
    C13 C8 S1 . . 119.28(15) y
    C2 C3 C4 . . 108.83(17) y
    C2 C3 S2 . . 124.14(15) y
    C4 C3 S2 . . 126.88(15) y
    C8 C9 C10 . . 118.6(2) n
    C8 C9 H9 . . 118.5(16) n
    C10 C9 H9 . . 122.9(16) n
    C4 C5 N1 . . 107.72(17) y
    C4 C5 H5 . . 133.1(15) n
    N1 C5 H5 . . 119.2(15) n
    C3 C2 N1 . . 106.29(16) y
    C3 C2 H2 . . 131.6(15) n
    N1 C2 H2 . . 122.1(15) n
    C5 C4 C3 . . 107.18(17) y
    C5 C4 H4 . . 126.1(16) n
    C3 C4 H4 . . 126.7(16) n
    C13 C12 C11 . . 120.2(2) n
    C13 C12 H12 . . 120.5(17) n
    C11 C12 H12 . . 119.4(17) n
    C10 C11 C12 . . 120.8(2) n
    C10 C11 H11 . . 119.5(17) n
    C12 C11 H11 . . 119.7(17) n
    C11 C10 C9 . . 120.0(2) n
    C11 C10 H10 . . 120.0(16) n
    C9 C10 H10 . . 120.0(16) n
    N2 C6 H6B . . 108.4(16) n
    N2 C6 H6A . . 113.5(17) n
    H6B C6 H6A . . 109(2) n
    N2 C6 H6C . . 105.7(17) n
    H6B C6 H6C . . 111(2) n
    H6A C6 H6C . . 109(2) n
    C12 C13 C8 . . 118.2(2) n
    C12 C13 H13 . . 120.7(18) n
    C8 C13 H13 . . 121.1(18) n
    N2 C7 H7B . . 110.8(15) n
    N2 C7 H7C . . 106.3(18) n
    H7B C7 H7C . . 112(2) n
    N2 C7 H7A . . 112.1(16) n
    H7B C7 H7A . . 106(2) n
    H7C C7 H7A . . 110(2) n
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
    O1 S1 N1 C2 . . . . 152.01(16) ?
    O2 S1 N1 C2 . . . . 22.53(18) ?
    C8 S1 N1 C2 . . . . -92.85(17) ?
    O1 S1 N1 C5 . . . . -31.49(18) ?
    O2 S1 N1 C5 . . . . -160.97(16) ?
    C8 S1 N1 C5 . . . . 83.65(17) ?
    O4 S2 N2 C7 . . . . -177.60(15) ?
    O3 S2 N2 C7 . . . . -48.07(17) ?
    C3 S2 N2 C7 . . . . 67.02(17) ?
    O4 S2 N2 C6 . . . . 47.99(18) ?
    O3 S2 N2 C6 . . . . 177.53(16) ?
    C3 S2 N2 C6 . . . . -67.38(17) ?
    O1 S1 C8 C9 . . . . 1.74(19) ?
    O2 S1 C8 C9 . . . . 137.21(16) ?
    N1 S1 C8 C9 . . . . -110.55(16) ?
    O1 S1 C8 C13 . . . . -176.78(16) ?
    O2 S1 C8 C13 . . . . -41.32(19) ?
    N1 S1 C8 C13 . . . . 70.93(18) ?
    O4 S2 C3 C2 . . . . 153.46(17) ?
    O3 S2 C3 C2 . . . . 23.6(2) ?
    N2 S2 C3 C2 . . . . -91.01(18) ?
    O4 S2 C3 C4 . . . . -31.5(2) ?
    O3 S2 C3 C4 . . . . -161.35(17) ?
    N2 S2 C3 C4 . . . . 84.05(19) ?
    C13 C8 C9 C10 . . . . 1.3(3) ?
    S1 C8 C9 C10 . . . . -177.20(16) ?
    C2 N1 C5 C4 . . . . -1.1(2) ?
    S1 N1 C5 C4 . . . . -178.02(15) ?
    C4 C3 C2 N1 . . . . -0.6(2) ?
    S2 C3 C2 N1 . . . . 175.20(14) ?
    C5 N1 C2 C3 . . . . 1.0(2) ?
    S1 N1 C2 C3 . . . . 177.97(14) ?
    N1 C5 C4 C3 . . . . 0.6(2) ?
    C2 C3 C4 C5 . . . . 0.0(2) ?
    S2 C3 C4 C5 . . . . -175.69(15) ?
    C13 C12 C11 C10 . . . . 1.0(4) ?
    C12 C11 C10 C9 . . . . 0.7(3) ?
    C8 C9 C10 C11 . . . . -1.8(3) ?
    C11 C12 C13 C8 . . . . -1.5(3) ?
    C9 C8 C13 C12 . . . . 0.3(3) ?
    S1 C8 C13 C12 . . . . 178.80(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
    _geom_hbond_publ_flag
    C4 H4 O1 4_665 0.89(2) 2.57(2) 3.325(3) 143(2) n
    C6 H6B O4 . 0.95(3) 2.51(3) 2.913(3) 105.9(19) n
    C7 H7B O3 . 0.97(3) 2.46(2) 2.891(3) 106.5(17) n
    C9 H9 O1 . 0.89(2) 2.48(2) 2.887(2) 108.6(19) n
    C10 H10 O2 1_455 0.94(2) 2.48(3) 3.317(3) 150(2) n
    C11 H11 O3 3_665 0.93(3) 2.52(3) 3.404(3) 160(2) n
    C13 H13 O3 3_765 0.89(3) 2.46(3) 3.349(3) 176(2) n
data_global
_journal_date_recd_electronic     2006-01-19
_journal_date_accepted     2006-02-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue      3
_journal_page_first     o980
_journal_page_last     o982
_journal_paper_category     EO
_journal_coeditor_code     FL2003
_publ_contact_author_name     'Dr David A. Grossie'
_publ_contact_author_address
;
Department of Chemistry
Wright State University
Dayton
Ohio 45435
USA
;
_publ_contact_author_email     david.grossie@wright.edu
_publ_contact_author_fax     '937 775 2717'
_publ_contact_author_phone     '937 775 2210'
_publ_section_title
;
N,N-Dimethyl-1-phenylsulfonyl-1H-pyrrole-3-sulfonamide
;
loop_
    _publ_author_name
    _publ_author_address
    'Grossie, David A.'
;
Department of Chemistry
Wright State University
Dayton
Ohio 45435
USA
;
    'Malwitz, David J.'
;
Department of Chemistry
Wright State University
Dayton
Ohio 45435
USA
;
    'Ketcha, Daniel M.'
;
Department of Chemistry
Wright State University
Dayton
Ohio 45435
USA
;
