#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/12/2221220.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_2221220
loop_
_publ_author_name
'Seshadri, P. R.'
'Balakrishnan, B.'
'Ilangovan, K.'
'Sureshbabu, R.'
'Mohanakrishnan, A. K.'
_publ_section_title
;
 2,5-Dimethyl-1-phenylsulfonyl-1H-pyrrole-3,4-dicarbaldehyde
;
_journal_coeditor_code           WN2307
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o531
_journal_paper_doi               10.1107/S1600536809004425
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H13 N O4 S'
_chemical_formula_moiety         'C14 H13 N O4 S'
_chemical_formula_sum            'C14 H13 N O4 S'
_chemical_formula_weight         291.31
_chemical_name_systematic
;
2,5-Dimethyl-1-phenylsulfonyl-1H-pyrrole-3,4-dicarbaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.700(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0257(3)
_cell_length_b                   12.6240(5)
_cell_length_c                   11.9914(5)
_cell_measurement_reflns_used    6814
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.23
_cell_measurement_theta_min      2.35
_cell_volume                     1353.99(9)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEXII (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)
;
_computing_publication_material  'PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Kappa-APEXII area-detector'
_diffrn_measurement_method       ω
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19609
_diffrn_reflns_theta_full        32.23
_diffrn_reflns_theta_max         32.23
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.9515
_exptl_absorpt_correction_T_min  0.9398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.416
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         4736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0787P)²+0.2246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1537
_reflns_number_gt                3164
_reflns_number_total             4736
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2307.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221220
_cod_database_fobs_code          2221220
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'
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_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
_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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741714
