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###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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/  #
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data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2,5-Dimethyl-1-phenylsulfonyl-1H-pyrrole-3,4-dicarbaldehyde
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H13 N O4 S'
_chemical_formula_sum     'C14 H13 N O4 S'
_chemical_formula_iupac     'C14 H13 N O4 S'
_chemical_formula_weight     291.31
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
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     9.0257(3)
_cell_length_b     12.6240(5)
_cell_length_c     11.9914(5)
_cell_angle_alpha     90.00
_cell_angle_beta     97.700(2)
_cell_angle_gamma     90.00
_cell_volume     1353.99(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6814
_cell_measurement_theta_min     2.35
_cell_measurement_theta_max     32.23
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.429
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     608
_exptl_absorpt_coefficient_mu     0.251
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2001)'
_exptl_absorpt_correction_T_min     0.9398
_exptl_absorpt_correction_T_max     0.9515
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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 Kappa-APEXII area-detector'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     19609
_diffrn_reflns_av_R_equivalents     0.0317
_diffrn_reflns_av_sigmaI/netI     0.0254
_diffrn_reflns_theta_min     2.35
_diffrn_reflns_theta_max     32.23
_diffrn_reflns_theta_full     32.23
_diffrn_measured_fraction_theta_max     0.989
_diffrn_measured_fraction_theta_full     0.989
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     ?
_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 >
σ(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     4736
_reflns_number_gt     3164
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0749
_refine_ls_R_factor_gt     0.0482
_refine_ls_wR_factor_gt     0.1323
_refine_ls_wR_factor_ref     0.1537
_refine_ls_goodness_of_fit_ref     1.003
_refine_ls_restrained_S_all     1.003
_refine_ls_number_reflns     4736
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
       'calc w = 1/[σ²(Fo²)+(0.0787P)²+0.2246P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.194
_refine_diff_density_min     -0.416
_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     'APEXII (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)
;
_computing_publication_material     'PARST (Nardelli, 1995)'
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 0.51190(5) 0.21083(3) 0.25629(3) 0.05026(14) Uani d . 1 . .
    N N 0.56878(14) 0.29263(9) 0.36572(10) 0.0417(3) Uani d . 1 . .
    O O1 0.64275(15) 0.17150(11) 0.21659(11) 0.0704(4) Uani d . 1 . .
    O O3 0.82639(16) 0.54763(12) 0.58440(12) 0.0777(4) Uani d . 1 . .
    O O2 0.40939(17) 0.13956(10) 0.29555(12) 0.0743(4) Uani d . 1 . .
    O O4 0.49857(19) 0.36086(17) 0.70677(12) 0.1023(6) Uani d . 1 . .
    C C1 0.51247(15) 0.29778(11) 0.46937(11) 0.0422(3) Uani d . 1 . .
    C C2 0.59280(15) 0.37280(11) 0.53213(11) 0.0404(3) Uani d . 1 . .
    C C3 0.69918(14) 0.41747(11) 0.46621(11) 0.0383(3) Uani d . 1 . .
    C C4 0.68371(15) 0.36717(11) 0.36473(11) 0.0412(3) Uani d . 1 . .
    C C5 0.80621(18) 0.50177(13) 0.49571(14) 0.0524(4) Uani d . 1 . .
    H H5 0.8646 0.5223 0.4412 0.063 Uiso calc R 1 . .
    C C6 0.57651(19) 0.40278(16) 0.64774(13) 0.0579(4) Uani d . 1 . .
    H H6 0.6327 0.4602 0.6779 0.069 Uiso calc R 1 . .
    C C7 0.3863(2) 0.23246(17) 0.50008(16) 0.0661(5) Uani d . 1 . .
    H H7A 0.3587 0.2571 0.5702 0.099 Uiso calc R 1 . .
    H H7B 0.4168 0.1597 0.5075 0.099 Uiso calc R 1 . .
    H H7C 0.3022 0.2386 0.4423 0.099 Uiso calc R 1 . .
    C C8 0.7684(2) 0.38292(17) 0.26769(14) 0.0662(5) Uani d . 1 . .
    H H8A 0.8349 0.4421 0.2825 0.099 Uiso calc R 1 . .
    H H8B 0.6997 0.3965 0.2009 0.099 Uiso calc R 1 . .
    H H8C 0.8253 0.3203 0.2571 0.099 Uiso calc R 1 . .
    C C9 0.41822(17) 0.29562(12) 0.15557(12) 0.0455(3) Uani d . 1 . .
    C C10 0.4612(2) 0.29939(16) 0.04944(14) 0.0604(4) Uani d . 1 . .
    H H10 0.5403 0.2583 0.0315 0.072 Uiso calc R 1 . .
    C C11 0.3837(3) 0.3659(2) -0.02973(16) 0.0767(6) Uani d . 1 . .
    H H11 0.4104 0.3696 -0.1019 0.092 Uiso calc R 1 . .
    C C12 0.2683(3) 0.42608(17) -0.00229(17) 0.0780(6) Uani d . 1 . .
    H H12 0.2176 0.4707 -0.0561 0.094 Uiso calc R 1 . .
    C C13 0.2260(3) 0.42188(16) 0.10310(18) 0.0744(6) Uani d . 1 . .
    H H13 0.1476 0.4638 0.1207 0.089 Uiso calc R 1 . .
    C C14 0.3000(2) 0.35534(13) 0.18281(14) 0.0579(4) Uani d . 1 . .
    H H14 0.2708 0.3507 0.2541 0.069 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0664(3) 0.0385(2) 0.0462(2) -0.00334(15) 0.00855(17) -0.00739(14)
    N 0.0513(6) 0.0408(6) 0.0347(5) -0.0058(5) 0.0120(5) -0.0013(4)
    O1 0.0800(8) 0.0655(8) 0.0655(8) 0.0209(7) 0.0084(6) -0.0213(6)
    O3 0.0858(9) 0.0823(10) 0.0652(8) -0.0240(7) 0.0105(7) -0.0272(7)
    O2 0.1039(10) 0.0500(7) 0.0681(8) -0.0305(7) 0.0080(7) 0.0000(6)
    O4 0.1016(12) 0.1637(17) 0.0496(8) -0.0353(11) 0.0398(8) -0.0136(9)
    C1 0.0459(7) 0.0463(7) 0.0362(6) -0.0003(5) 0.0121(5) 0.0061(5)
    C2 0.0429(6) 0.0467(7) 0.0333(6) 0.0049(5) 0.0115(5) 0.0032(5)
    C3 0.0418(6) 0.0389(7) 0.0347(6) 0.0024(5) 0.0074(5) 0.0024(5)
    C4 0.0465(7) 0.0430(7) 0.0358(6) -0.0019(5) 0.0123(5) 0.0015(5)
    C5 0.0560(8) 0.0535(9) 0.0480(8) -0.0081(7) 0.0078(6) -0.0012(7)
    C6 0.0595(9) 0.0796(12) 0.0366(7) 0.0025(8) 0.0143(6) -0.0055(7)
    C7 0.0662(10) 0.0772(12) 0.0595(10) -0.0208(9) 0.0248(8) 0.0053(9)
    C8 0.0784(12) 0.0817(13) 0.0445(9) -0.0255(10) 0.0295(8) -0.0068(8)
    C9 0.0551(8) 0.0435(7) 0.0379(7) -0.0089(6) 0.0067(6) -0.0098(5)
    C10 0.0643(10) 0.0774(12) 0.0411(8) -0.0095(8) 0.0134(7) -0.0091(8)
    C11 0.0942(15) 0.0952(16) 0.0402(9) -0.0202(12) 0.0072(9) 0.0005(9)
    C12 0.1054(16) 0.0665(12) 0.0567(11) -0.0007(11) -0.0086(11) 0.0022(9)
    C13 0.0900(14) 0.0586(11) 0.0710(12) 0.0162(10) -0.0029(10) -0.0134(9)
    C14 0.0742(11) 0.0527(9) 0.0472(9) 0.0036(8) 0.0099(8) -0.0136(7)
_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 O2 . 1.4155(13) ?
    S1 O1 . 1.4209(13) ?
    S1 N . 1.6945(12) ?
    S1 C9 . 1.7452(17) ?
    N C4 . 1.4018(17) ?
    N C1 . 1.4060(17) ?
    O3 C5 . 1.203(2) ?
    O4 C6 . 1.187(2) ?
    C1 C2 . 1.358(2) ?
    C1 C7 . 1.492(2) ?
    C2 C3 . 1.4382(18) ?
    C2 C6 . 1.463(2) ?
    C3 C4 . 1.3631(19) ?
    C3 C5 . 1.449(2) ?
    C4 C8 . 1.4890(19) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 H7A . 0.9600 ?
    C7 H7B . 0.9600 ?
    C7 H7C . 0.9600 ?
    C8 H8A . 0.9600 ?
    C8 H8B . 0.9600 ?
    C8 H8C . 0.9600 ?
    C9 C10 . 1.380(2) ?
    C9 C14 . 1.381(2) ?
    C10 C11 . 1.385(3) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.364(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.370(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.376(3) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
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 . . 119.94(9) ?
    O2 S1 N . . 105.88(7) ?
    O1 S1 N . . 107.05(7) ?
    O2 S1 C9 . . 110.02(8) ?
    O1 S1 C9 . . 109.26(8) ?
    N S1 C9 . . 103.33(7) ?
    C4 N C1 . . 109.39(11) ?
    C4 N S1 . . 123.39(9) ?
    C1 N S1 . . 127.22(10) ?
    C2 C1 N . . 107.03(11) ?
    C2 C1 C7 . . 128.14(13) ?
    N C1 C7 . . 124.83(14) ?
    C1 C2 C3 . . 108.37(12) ?
    C1 C2 C6 . . 126.27(13) ?
    C3 C2 C6 . . 125.35(14) ?
    C4 C3 C2 . . 108.18(12) ?
    C4 C3 C5 . . 123.06(13) ?
    C2 C3 C5 . . 128.76(13) ?
    C3 C4 N . . 107.02(11) ?
    C3 C4 C8 . . 129.31(14) ?
    N C4 C8 . . 123.67(13) ?
    O3 C5 C3 . . 125.90(15) ?
    O3 C5 H5 . . 117.1 ?
    C3 C5 H5 . . 117.1 ?
    O4 C6 C2 . . 126.33(18) ?
    O4 C6 H6 . . 116.8 ?
    C2 C6 H6 . . 116.8 ?
    C1 C7 H7A . . 109.5 ?
    C1 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C1 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    C4 C8 H8A . . 109.5 ?
    C4 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C4 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C10 C9 C14 . . 121.40(16) ?
    C10 C9 S1 . . 119.29(14) ?
    C14 C9 S1 . . 119.29(12) ?
    C9 C10 C11 . . 118.31(18) ?
    C9 C10 H10 . . 120.8 ?
    C11 C10 H10 . . 120.8 ?
    C12 C11 C10 . . 120.27(18) ?
    C12 C11 H11 . . 119.9 ?
    C10 C11 H11 . . 119.9 ?
    C11 C12 C13 . . 121.2(2) ?
    C11 C12 H12 . . 119.4 ?
    C13 C12 H12 . . 119.4 ?
    C12 C13 C14 . . 119.66(19) ?
    C12 C13 H13 . . 120.2 ?
    C14 C13 H13 . . 120.2 ?
    C13 C14 C9 . . 119.18(16) ?
    C13 C14 H14 . . 120.4 ?
    C9 C14 H14 . . 120.4 ?
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
    O2 S1 N C4 . . . . 172.55(12) ?
    O1 S1 N C4 . . . . 43.51(14) ?
    C9 S1 N C4 . . . . -71.78(13) ?
    O2 S1 N C1 . . . . -7.23(15) ?
    O1 S1 N C1 . . . . -136.28(13) ?
    C9 S1 N C1 . . . . 108.43(13) ?
    C4 N C1 C2 . . . . -1.03(16) ?
    S1 N C1 C2 . . . . 178.78(10) ?
    C4 N C1 C7 . . . . 178.16(15) ?
    S1 N C1 C7 . . . . -2.0(2) ?
    N C1 C2 C3 . . . . 1.33(16) ?
    C7 C1 C2 C3 . . . . -177.83(16) ?
    N C1 C2 C6 . . . . -177.86(14) ?
    C7 C1 C2 C6 . . . . 3.0(3) ?
    C1 C2 C3 C4 . . . . -1.18(16) ?
    C6 C2 C3 C4 . . . . 178.02(14) ?
    C1 C2 C3 C5 . . . . 178.14(14) ?
    C6 C2 C3 C5 . . . . -2.7(2) ?
    C2 C3 C4 N . . . . 0.53(15) ?
    C5 C3 C4 N . . . . -178.84(13) ?
    C2 C3 C4 C8 . . . . -179.04(17) ?
    C5 C3 C4 C8 . . . . 1.6(3) ?
    C1 N C4 C3 . . . . 0.29(16) ?
    S1 N C4 C3 . . . . -179.53(10) ?
    C1 N C4 C8 . . . . 179.88(15) ?
    S1 N C4 C8 . . . . 0.1(2) ?
    C4 C3 C5 O3 . . . . -178.68(17) ?
    C2 C3 C5 O3 . . . . 2.1(3) ?
    C1 C2 C6 O4 . . . . 5.9(3) ?
    C3 C2 C6 O4 . . . . -173.12(19) ?
    O2 S1 C9 C10 . . . . -122.33(14) ?
    O1 S1 C9 C10 . . . . 11.30(15) ?
    N S1 C9 C10 . . . . 125.00(13) ?
    O2 S1 C9 C14 . . . . 55.92(14) ?
    O1 S1 C9 C14 . . . . -170.46(12) ?
    N S1 C9 C14 . . . . -56.75(13) ?
    C14 C9 C10 C11 . . . . 0.7(3) ?
    S1 C9 C10 C11 . . . . 178.93(14) ?
    C9 C10 C11 C12 . . . . 0.3(3) ?
    C10 C11 C12 C13 . . . . -0.4(3) ?
    C11 C12 C13 C14 . . . . -0.5(3) ?
    C12 C13 C14 C9 . . . . 1.4(3) ?
    C10 C9 C14 C13 . . . . -1.6(2) ?
    S1 C9 C14 C13 . . . . -179.77(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
    _geom_hbond_publ_flag
    C6 H6 O3 . 0.93 2.46 3.077(2) 124.0 yes
    C7 H7A O4 . 0.96 2.33 3.021(3) 128.0 yes
    C11 H11 O4 1_554 0.93 2.53 3.456(2) 174.0 yes
    C13 H13 O2 2-555 0.93 2.52 3.304(2) 143.0 yes
    C14 H14 O3 3_666 0.93 2.57 3.383(2) 146.0 yes
data_global
_journal_date_recd_electronic     2009-01-20
_journal_date_accepted     2009-02-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      3
_journal_page_first     o531
_journal_page_last     o531
_journal_paper_category     QO
_journal_coeditor_code     WN2307
_publ_contact_author_name     'Dr P. R. Seshadri'
_publ_contact_author_address
;
Postgraduate and Research Department of Physics
Agurchand Manmull Jain College
Chennai 600 114
India
;
_publ_contact_author_email     seshadri_pr@yahoo.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '044 22246056'
_publ_section_title
;
2,5-Dimethyl-1-phenylsulfonyl-1H-pyrrole-3,4-dicarbaldehyde
;
loop_
    _publ_author_name
    _publ_author_address
    'Seshadri, P. R.'
;
Postgraduate and Research Department of Physics
Agurchand Manmull Jain College
Chennai 600 114
India
;
    'Balakrishnan, B.'
;
Department of Physics
P. T. Lee Chengalvaraya Naicker College of Engineering and Technology
Kancheepuram 631 502
India
;
    'Ilangovan, K.'
;
Postgraduate and Research Department of Physics
RKM Vivekananda College
Chennai 600 004
India
;
    'Sureshbabu, R.'
;
Department of Organic Chemistry
University of Madras
Guindy Campus
Chennai 600 025
India
;
    'Mohanakrishnan, A. K.'
;
Department of Organic Chemistry
University of Madras
Guindy Campus
Chennai 600 025
India
;
