#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/31/2213191.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_2213191
loop_
_publ_author_name
'Roy, Sujata'
'Gribble, Gordon W.'
'Jasinski, Jerry P.'
_publ_section_title
;
 2-Nitro-1-(phenylsulfonyl)-1H-indole
;
_journal_coeditor_code           BV2055
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2628
_journal_page_last               o2629
_journal_paper_doi               10.1107/S160053680701896X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H10 N2 O4 S'
_chemical_formula_moiety         'C14 H10 N2 O4 S'
_chemical_formula_sum            'C14 H10 N2 O4 S'
_chemical_formula_weight         302.30
_chemical_name_systematic
;
2-Nitro-1-(phenylsulfonyl)-1H-indole
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.7613(16)
_cell_length_b                   7.4192(5)
_cell_length_c                   20.856(2)
_cell_measurement_reflns_used    10523
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.0360
_cell_measurement_theta_min      2.9140
_cell_volume                     2593.6(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17003
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        26.30
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0.01
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.9312
_exptl_absorpt_correction_T_min  0.8958
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.469
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0283P)²+2.3886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1238
_reflns_number_gt                3766
_reflns_number_total             4394
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2055.cif
_cod_data_source_block           I
_cod_database_code               2213191
_cod_database_fobs_code          2213191
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -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_occupancy
S S1 0.94799(2) 0.08864(5) 0.16209(2) 0.01707(11) Uani d 1
O O1 0.94218(8) -0.08211(16) 0.13062(7) 0.0234(3) Uani d 1
O O2 0.97904(8) 0.09802(19) 0.22576(6) 0.0238(3) Uani d 1
O O3 0.86464(8) 0.12276(18) 0.03387(7) 0.0244(3) Uani d 1
O O4 0.74991(9) -0.0158(2) 0.03487(7) 0.0318(3) Uani d 1
N N1 0.85413(9) 0.17471(19) 0.16669(7) 0.0176(3) Uani d 1
N N2 0.80306(9) 0.0728(2) 0.06086(8) 0.0213(3) Uani d 1
C C2 0.79086(10) 0.1226(2) 0.12643(9) 0.0189(3) Uani d 1
C C3 0.71886(11) 0.1504(2) 0.15417(10) 0.0209(3) Uani d 1
C C4 0.68306(12) 0.2796(2) 0.26571(11) 0.0259(4) Uani d 1
C C5 0.71648(13) 0.3447(3) 0.32136(11) 0.0280(4) Uani d 1
C C6 0.79960(13) 0.3558(3) 0.32882(10) 0.0262(4) Uani d 1
C C7 0.85161(12) 0.3023(2) 0.28069(9) 0.0227(4) Uani d 1
C C8 0.73420(11) 0.2226(2) 0.21660(9) 0.0203(3) Uani d 1
C C9 0.81784(10) 0.2354(2) 0.22471(9) 0.0182(3) Uani d 1
C C10 1.00010(10) 0.2430(2) 0.11379(8) 0.0168(3) Uani d 1
C C11 1.04467(11) 0.1783(2) 0.06261(9) 0.0201(3) Uani d 1
C C12 1.08910(11) 0.3005(2) 0.02668(9) 0.0220(4) Uani d 1
C C13 1.08692(11) 0.4834(2) 0.04158(9) 0.0222(4) Uani d 1
C C14 1.04190(11) 0.5454(2) 0.09313(9) 0.0209(3) Uani d 1
C C15 0.99858(11) 0.4248(2) 0.13027(9) 0.0187(3) Uani d 1
H H1 0.6707(15) 0.133(3) 0.1325(11) 0.023(6) Uiso d 1
H H2 0.6295(16) 0.272(3) 0.2594(13) 0.034(7) Uiso d 1
H H3 0.6857(16) 0.384(3) 0.3565(12) 0.029(6) Uiso d 1
H H4 0.8192(16) 0.404(3) 0.3699(12) 0.030(6) Uiso d 1
H H5 0.9073(15) 0.313(3) 0.2855(11) 0.027(6) Uiso d 1
H H6 1.0411(14) 0.056(3) 0.0498(11) 0.023(6) Uiso d 1
H H7 1.1203(15) 0.261(3) -0.0072(12) 0.029(6) Uiso d 1
H H8 1.1155(14) 0.570(3) 0.0155(11) 0.023(6) Uiso d 1
H H9 1.0422(14) 0.677(3) 0.1044(11) 0.022(6) Uiso d 1
H H10 0.9713(14) 0.466(3) 0.1665(11) 0.020(5) Uiso 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 0.0000 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
O2 S1 O1 119.66(8)
O2 S1 N1 105.44(8)
O1 S1 N1 107.19(8)
O2 S1 C10 108.67(8)
O1 S1 C10 110.37(8)
N1 S1 C10 104.32(8)
C2 N1 C9 105.75(14)
C2 N1 S1 124.09(12)
C9 N1 S1 124.10(12)
O4 N2 O3 124.38(17)
O4 N2 C2 117.03(16)
O3 N2 C2 118.58(15)
C3 C2 N1 112.02(16)
C3 C2 N2 125.09(17)
N1 C2 N2 122.25(15)
C2 C3 C8 106.59(16)
C2 C3 H1 122.8(15)
C8 C3 H1 130.4(15)
C5 C4 C8 118.27(18)
C5 C4 H2 123.1(17)
C8 C4 H2 118.6(17)
C4 C5 C6 121.17(19)
C4 C5 H3 122.8(16)
C6 C5 H3 116.1(16)
C7 C6 C5 121.8(2)
C7 C6 H4 121.6(16)
C5 C6 H4 116.6(16)
C6 C7 C9 117.02(18)
C6 C7 H5 121.4(15)
C9 C7 H5 121.6(15)
C4 C8 C9 119.89(18)
C4 C8 C3 131.94(18)
C9 C8 C3 108.17(16)
C7 C9 C8 121.87(16)
C7 C9 N1 130.66(16)
C8 C9 N1 107.44(15)
C11 C10 C15 122.33(16)
C11 C10 S1 118.85(13)
C15 C10 S1 118.74(13)
C10 C11 C12 118.43(16)
C10 C11 H6 120.9(14)
C12 C11 H6 120.4(14)
C11 C12 C13 120.04(17)
C11 C12 H7 120.3(16)
C13 C12 H7 119.6(16)
C14 C13 C12 120.57(17)
C14 C13 H8 118.9(14)
C12 C13 H8 120.6(14)
C15 C14 C13 120.11(16)
C15 C14 H9 120.0(13)
C13 C14 H9 119.9(13)
C14 C15 C10 118.50(16)
C14 C15 H10 119.7(14)
C10 C15 H10 121.7(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4280(14)
S1 O1 1.4301(13)
S1 N1 1.7006(15)
S1 C10 1.7576(17)
O3 N2 1.233(2)
O4 N2 1.233(2)
N1 C2 1.407(2)
N1 C9 1.427(2)
N2 C2 1.431(2)
C2 C3 1.354(2)
C3 C8 1.431(3)
C3 H1 0.93(3)
C4 C5 1.376(3)
C4 C8 1.401(3)
C4 H2 0.91(3)
C5 C6 1.404(3)
C5 H3 0.94(3)
C6 C7 1.387(3)
C6 H4 0.98(3)
C7 C9 1.389(3)
C7 H5 0.94(3)
C8 C9 1.415(2)
C10 C11 1.389(2)
C10 C15 1.392(2)
C11 C12 1.392(3)
C11 H6 0.95(2)
C12 C13 1.393(3)
C12 H7 0.93(3)
C13 C14 1.392(3)
C13 H8 0.97(2)
C14 C15 1.389(3)
C14 H9 1.01(2)
C15 H10 0.94(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9252645
