#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/18/2231847.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_2231847
loop_
_publ_author_name
'Ramathilagam, C.'
'Saravanan, V.'
'Mohanakrishnan, A. K.'
'Umarani, P. R.'
'Manivannan, V.'
_publ_section_title
;
 2-Methyl-1-phenylsulfonyl-1H-indole-3-carbaldehyde
;
_journal_coeditor_code           CI5199
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2614
_journal_paper_doi               10.1107/S1600536811035665
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H13 N O3 S'
_chemical_formula_moiety         'C16 H13 N O3 S'
_chemical_formula_sum            'C16 H13 N O3 S'
_chemical_formula_weight         299.33
_chemical_name_systematic
;
2-Methyl-1-phenylsulfonyl-1H-indole-3-carbaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 93.1260(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6305(5)
_cell_length_b                   8.4039(4)
_cell_length_c                   14.3128(8)
_cell_measurement_reflns_used    4242
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.81
_cell_volume                     1396.87(12)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18442
_diffrn_reflns_theta_full        30.47
_diffrn_reflns_theta_max         30.47
_diffrn_reflns_theta_min         2.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_correction_T_min  0.9489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0407
_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)+(0.051P)²+0.3293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                3212
_reflns_number_total             4242
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5199.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2Ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2231847
_cod_database_fobs_code          2231847
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'
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
C C1 0.51033(11) 1.03657(16) 0.11957(9) 0.0372(3) Uani d . 1 1
C C2 0.62740(13) 1.0134(2) 0.14228(11) 0.0488(3) Uani d . 1 1
H H2 0.6794 1.0968 0.1382 0.059 Uiso calc R 1 1
C C3 0.66431(13) 0.8654(2) 0.17072(12) 0.0541(4) Uani d . 1 1
H H3 0.7420 0.8486 0.1863 0.065 Uiso calc R 1 1
C C4 0.58737(14) 0.7403(2) 0.17652(11) 0.0509(4) Uani d . 1 1
H H4 0.6148 0.6412 0.1961 0.061 Uiso calc R 1 1
C C5 0.47145(13) 0.75842(17) 0.15415(10) 0.0442(3) Uani d . 1 1
H H5 0.4203 0.6739 0.1581 0.053 Uiso calc R 1 1
C C6 0.43434(11) 0.90840(16) 0.12546(9) 0.0356(3) Uani d . 1 1
C C7 0.33085(13) 1.12984(17) 0.07792(10) 0.0429(3) Uani d . 1 1
C C8 0.44359(12) 1.17348(17) 0.08955(9) 0.0412(3) Uani d . 1 1
C C9 0.22868(16) 1.2312(2) 0.05301(14) 0.0655(5) Uani d . 1 1
H H9A 0.2527 1.3399 0.0472 0.098 Uiso calc R 1 1
H H9B 0.1747 1.2233 0.1012 0.098 Uiso calc R 1 1
H H9C 0.1929 1.1958 -0.0053 0.098 Uiso calc R 1 1
C C10 0.48781(17) 1.3321(2) 0.07368(12) 0.0559(4) Uani d . 1 1
H H10 0.4355 1.4109 0.0545 0.067 Uiso calc R 1 1
C C11 0.13200(11) 0.92243(17) 0.19354(9) 0.0395(3) Uani d . 1 1
C C12 0.18938(12) 0.90248(19) 0.27999(10) 0.0457(3) Uani d . 1 1
H H12 0.2640 0.8624 0.2845 0.055 Uiso calc R 1 1
C C13 0.13415(16) 0.9431(2) 0.35933(11) 0.0569(4) Uani d . 1 1
H H13 0.1717 0.9313 0.4180 0.068 Uiso calc R 1 1
C C14 0.02338(16) 1.0010(2) 0.35188(13) 0.0624(4) Uani d . 1 1
H H14 -0.0138 1.0270 0.4058 0.075 Uiso calc R 1 1
C C15 -0.03304(14) 1.0211(2) 0.26584(13) 0.0613(4) Uani d . 1 1
H H15 -0.1078 1.0608 0.2618 0.074 Uiso calc R 1 1
C C16 0.02108(12) 0.9824(2) 0.18524(11) 0.0516(4) Uani d . 1 1
H H16 -0.0163 0.9964 0.1267 0.062 Uiso calc R 1 1
N N1 0.32271(9) 0.96653(14) 0.09734(8) 0.0411(3) Uani d . 1 1
O O1 0.23308(10) 0.69878(14) 0.10309(9) 0.0575(3) Uani d . 1 1
O O2 0.13304(10) 0.91043(19) 0.01249(8) 0.0667(4) Uani d . 1 1
O O3 0.58819(13) 1.36833(15) 0.08380(10) 0.0742(4) Uani d . 1 1
S S1 0.20015(3) 0.86138(5) 0.09314(2) 0.04468(12) Uani d . 1 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
C2 C1 C6 119.32(13)
C2 C1 C8 133.15(13)
C6 C1 C8 107.53(12)
C3 C2 C1 118.80(14)
C3 C2 H2 120.6
C1 C2 H2 120.6
C2 C3 C4 120.88(14)
C2 C3 H3 119.6
C4 C3 H3 119.6
C5 C4 C3 121.96(15)
C5 C4 H4 119.0
C3 C4 H4 119.0
C4 C5 C6 117.02(14)
C4 C5 H5 121.5
C6 C5 H5 121.5
C5 C6 C1 122.02(12)
C5 C6 N1 131.25(12)
C1 C6 N1 106.74(12)
C8 C7 N1 108.28(12)
C8 C7 C9 128.68(14)
N1 C7 C9 123.01(14)
C7 C8 C1 108.71(12)
C7 C8 C10 125.09(14)
C1 C8 C10 126.20(14)
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O3 C10 C8 124.15(17)
O3 C10 H10 117.9
C8 C10 H10 117.9
C12 C11 C16 121.52(13)
C12 C11 S1 118.64(10)
C16 C11 S1 119.77(11)
C13 C12 C11 118.90(14)
C13 C12 H12 120.6
C11 C12 H12 120.6
C14 C13 C12 120.02(15)
C14 C13 H13 120.0
C12 C13 H13 120.0
C15 C14 C13 120.82(15)
C15 C14 H14 119.6
C13 C14 H14 119.6
C14 C15 C16 120.14(15)
C14 C15 H15 119.9
C16 C15 H15 119.9
C15 C16 C11 118.59(14)
C15 C16 H16 120.7
C11 C16 H16 120.7
C7 N1 C6 108.71(11)
C7 N1 S1 125.08(10)
C6 N1 S1 126.14(10)
O2 S1 O1 119.54(8)
O2 S1 N1 107.77(7)
O1 S1 N1 106.19(6)
O2 S1 C11 109.16(7)
O1 S1 C11 109.24(7)
N1 S1 C11 103.76(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3962(19)
C1 C6 1.3988(18)
C1 C8 1.4404(19)
C2 C3 1.370(2)
C2 H2 0.93
C3 C4 1.386(2)
C3 H3 0.93
C4 C5 1.377(2)
C4 H4 0.93
C5 C6 1.3871(19)
C5 H5 0.93
C6 N1 1.4246(16)
C7 C8 1.363(2)
C7 N1 1.4046(19)
C7 C9 1.490(2)
C8 C10 1.451(2)
C9 H9A 0.96
C9 H9B 0.96
C9 H9C 0.96
C10 O3 1.207(2)
C10 H10 0.93
C11 C12 1.3835(19)
C11 C16 1.3841(19)
C11 S1 1.7552(14)
C12 C13 1.378(2)
C12 H12 0.93
C13 C14 1.376(2)
C13 H13 0.93
C14 C15 1.374(3)
C14 H14 0.93
C15 C16 1.383(2)
C15 H15 0.93
C16 H16 0.93
N1 S1 1.6753(12)
O1 S1 1.4242(13)
O2 S1 1.4190(12)
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
C5 H5 O1 . 0.93 2.28 2.8723(19) 121 y
C12 H12 O3 2_645 0.93 2.48 3.1664(19) 131 y
C16 H16 O2 3_575 0.93 2.48 3.388(2) 167 y
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
C6 C1 C2 C3 -0.7(2)
C8 C1 C2 C3 178.78(15)
C1 C2 C3 C4 0.3(2)
C2 C3 C4 C5 0.1(2)
C3 C4 C5 C6 -0.1(2)
C4 C5 C6 C1 -0.2(2)
C4 C5 C6 N1 179.63(14)
C2 C1 C6 C5 0.6(2)
C8 C1 C6 C5 -178.94(12)
C2 C1 C6 N1 -179.26(12)
C8 C1 C6 N1 1.17(14)
N1 C7 C8 C1 -1.48(16)
C9 C7 C8 C1 176.15(15)
N1 C7 C8 C10 178.30(13)
C9 C7 C8 C10 -4.1(3)
C2 C1 C8 C7 -179.31(15)
C6 C1 C8 C7 0.18(15)
C2 C1 C8 C10 0.9(2)
C6 C1 C8 C10 -179.60(13)
C7 C8 C10 O3 -179.51(16)
C1 C8 C10 O3 0.2(3)
C16 C11 C12 C13 0.2(2)
S1 C11 C12 C13 -176.90(13)
C11 C12 C13 C14 0.6(3)
C12 C13 C14 C15 -0.8(3)
C13 C14 C15 C16 0.2(3)
C14 C15 C16 C11 0.5(3)
C12 C11 C16 C15 -0.7(2)
S1 C11 C16 C15 176.34(13)
C8 C7 N1 C6 2.23(15)
C9 C7 N1 C6 -175.57(14)
C8 C7 N1 S1 179.33(10)
C9 C7 N1 S1 1.5(2)
C5 C6 N1 C7 178.03(14)
C1 C6 N1 C7 -2.08(14)
C5 C6 N1 S1 1.0(2)
C1 C6 N1 S1 -179.15(9)
C7 N1 S1 O2 41.89(14)
C6 N1 S1 O2 -141.51(11)
C7 N1 S1 O1 171.10(11)
C6 N1 S1 O1 -12.30(13)
C7 N1 S1 C11 -73.79(13)
C6 N1 S1 C11 102.82(12)
C12 C11 S1 O2 -172.81(12)
C16 C11 S1 O2 10.03(16)
C12 C11 S1 O1 54.80(13)
C16 C11 S1 O1 -122.36(13)
C12 C11 S1 N1 -58.13(13)
C16 C11 S1 N1 124.72(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8510362
