#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/30/2223014.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_2223014
loop_
_publ_author_name
'Thenmozhi, S.'
'Ranjith, S.'
'SubbiahPandi, A.'
'Dhayalan, V.'
'MohanaKrishnan, A. K.'
_publ_section_title
;
 N-(2-Formylphenyl)benzenesulfonamide
;
_journal_coeditor_code           CI2869
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2210
_journal_paper_doi               10.1107/S1600536809032681
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H11 N1 O3 S'
_chemical_formula_moiety         'C13 H11 N1 O3 S'
_chemical_formula_sum            'C13 H11 N O3 S'
_chemical_formula_weight         261.29
_chemical_name_systematic
;
N-(2-Formylphenyl)benzenesulfonamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.2930(10)
_cell_angle_beta                 77.9120(10)
_cell_angle_gamma                68.8260(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7656(2)
_cell_length_b                   9.0080(2)
_cell_length_c                   9.5855(2)
_cell_measurement_reflns_used    3960
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.3
_cell_measurement_theta_min      2.2
_cell_volume                     611.35(2)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15490
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         31.27
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.311
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0397
_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)+(0.0582P)²+0.1353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                3228
_reflns_number_total             3960
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2869.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_formula_sum        'C13 H11 N1 O3 S'
_cod_database_code               2223014
_cod_database_fobs_code          2223014
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.19429(17) 0.98956(14) 0.61966(13) 0.0409(2) Uani d . 1 . .
C C2 0.1595(2) 1.10035(15) 0.72614(15) 0.0470(3) Uani d . 1 . .
H H2 0.1207 1.0779 0.8210 0.056 Uiso calc R 1 . .
C C3 0.1827(2) 1.24378(17) 0.69056(18) 0.0563(3) Uani d . 1 . .
H H3 0.1595 1.3170 0.7626 0.068 Uiso calc R 1 . .
C C4 0.2392(3) 1.2813(2) 0.5513(2) 0.0695(5) Uani d . 1 . .
H H4 0.2547 1.3783 0.5292 0.083 Uiso calc R 1 . .
C C5 0.2722(3) 1.1734(2) 0.44619(19) 0.0675(4) Uani d . 1 . .
H H5 0.3085 1.1987 0.3517 0.081 Uiso calc R 1 . .
C C6 0.2529(2) 1.02670(18) 0.47720(15) 0.0503(3) Uani d . 1 . .
C C7 0.2926(3) 0.9189(3) 0.35857(18) 0.0692(5) Uani d . 1 . .
H H7 0.3264 0.9554 0.2677 0.083 Uiso calc R 1 . .
C C8 0.36455(18) 0.70690(14) 0.85278(13) 0.0413(3) Uani d . 1 . .
C C9 0.5123(2) 0.57064(16) 0.79634(16) 0.0519(3) Uani d . 1 . .
H H9 0.4963 0.5055 0.7325 0.062 Uiso calc R 1 . .
C C10 0.6827(2) 0.5337(2) 0.83658(19) 0.0628(4) Uani d . 1 . .
H H10 0.7829 0.4425 0.7999 0.075 Uiso calc R 1 . .
C C11 0.7062(2) 0.6304(2) 0.93052(19) 0.0621(4) Uani d . 1 . .
H H11 0.8225 0.6047 0.9563 0.074 Uiso calc R 1 . .
C C12 0.5587(2) 0.7649(2) 0.98675(18) 0.0599(4) Uani d . 1 . .
H H12 0.5758 0.8296 1.0503 0.072 Uiso calc R 1 . .
C C13 0.3853(2) 0.80416(16) 0.94909(15) 0.0487(3) Uani d . 1 . .
H H13 0.2847 0.8941 0.9877 0.058 Uiso calc R 1 . .
N N1 0.16942(19) 0.84378(14) 0.64708(14) 0.0509(3) Uani d . 1 . .
O O1 0.00479(14) 0.85915(13) 0.90061(12) 0.0576(3) Uani d . 1 . .
O O2 0.13222(17) 0.60899(13) 0.76162(14) 0.0649(3) Uani d . 1 . .
O O3 0.2861(2) 0.78653(18) 0.36620(14) 0.0795(4) Uani d . 1 . .
S S1 0.14948(5) 0.75289(4) 0.79852(4) 0.04575(11) Uani d . 1 . .
H H1 0.199(3) 0.790(2) 0.5767(19) 0.064(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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 N1 . . 123.02(12) ?
C2 C1 C6 . . 118.86(12) ?
N1 C1 C6 . . 118.10(12) ?
C3 C2 C1 . . 119.78(14) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C4 C3 C2 . . 121.69(15) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C5 C4 C3 . . 118.78(15) ?
C5 C4 H4 . . 120.6 ?
C3 C4 H4 . . 120.6 ?
C4 C5 C6 . . 121.51(16) ?
C4 C5 H5 . . 119.2 ?
C6 C5 H5 . . 119.2 ?
C5 C6 C1 . . 119.37(14) ?
C5 C6 C7 . . 117.69(16) ?
C1 C6 C7 . . 122.94(15) ?
O3 C7 C6 . . 126.49(17) ?
O3 C7 H7 . . 116.8 ?
C6 C7 H7 . . 116.8 ?
C13 C8 C9 . . 121.35(13) ?
C13 C8 S1 . . 120.66(10) ?
C9 C8 S1 . . 117.98(11) ?
C10 C9 C8 . . 118.75(15) ?
C10 C9 H9 . . 120.6 ?
C8 C9 H9 . . 120.6 ?
C11 C10 C9 . . 120.54(15) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C12 . . 120.40(15) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C11 C12 C13 . . 120.29(16) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C13 C8 . . 118.66(14) ?
C12 C13 H13 . . 120.7 ?
C8 C13 H13 . . 120.7 ?
C1 N1 S1 . . 128.49(9) ?
C1 N1 H1 . . 112.3(14) ?
S1 N1 H1 . . 116.5(13) ?
O1 S1 O2 . . 119.76(7) ?
O1 S1 N1 . . 109.04(7) ?
O2 S1 N1 . . 103.70(7) ?
O1 S1 C8 . . 108.57(7) ?
O2 S1 C8 . . 108.83(7) ?
N1 S1 C8 . . 106.08(6) ?
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
C1 C2 . 1.3900(17) ?
C1 N1 . 1.3957(17) ?
C1 C6 . 1.4052(19) ?
C2 C3 . 1.3797(19) ?
C2 H2 . 0.93 ?
C3 C4 . 1.375(2) ?
C3 H3 . 0.93 ?
C4 C5 . 1.365(3) ?
C4 H4 . 0.93 ?
C5 C6 . 1.390(2) ?
C5 H5 . 0.93 ?
C6 C7 . 1.453(2) ?
C7 O3 . 1.208(2) ?
C7 H7 . 0.93 ?
C8 C13 . 1.3838(18) ?
C8 C9 . 1.3871(18) ?
C8 S1 . 1.7515(14) ?
C9 C10 . 1.375(2) ?
C9 H9 . 0.93 ?
C10 C11 . 1.374(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.376(2) ?
C11 H11 . 0.93 ?
C12 C13 . 1.383(2) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
N1 S1 . 1.6265(13) ?
N1 H1 . 0.798(18) ?
O1 S1 . 1.4212(10) ?
O2 S1 . 1.4241(10) ?
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
N1 H1 O3 . 0.80(2) 1.99(2) 2.6751(19) 144(2)
C2 H2 O1 . 0.93 2.46 3.0879(18) 125
C3 H3 O2 1_565 0.93 2.56 3.2691(19) 133
C5 H5 Cg1 2_676 0.93 2.80 3.700(2) 162
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
N1 C1 C2 C3 . . . . -178.37(13) ?
C6 C1 C2 C3 . . . . 0.1(2) ?
C1 C2 C3 C4 . . . . 0.2(2) ?
C2 C3 C4 C5 . . . . 0.3(3) ?
C3 C4 C5 C6 . . . . -1.1(3) ?
C4 C5 C6 C1 . . . . 1.4(3) ?
C4 C5 C6 C7 . . . . -179.47(18) ?
C2 C1 C6 C5 . . . . -0.8(2) ?
N1 C1 C6 C5 . . . . 177.67(14) ?
C2 C1 C6 C7 . . . . -179.97(14) ?
N1 C1 C6 C7 . . . . -1.4(2) ?
C5 C6 C7 O3 . . . . 178.68(18) ?
C1 C6 C7 O3 . . . . -2.2(3) ?
C13 C8 C9 C10 . . . . -0.7(2) ?
S1 C8 C9 C10 . . . . 179.30(11) ?
C8 C9 C10 C11 . . . . -0.2(2) ?
C9 C10 C11 C12 . . . . 0.6(2) ?
C10 C11 C12 C13 . . . . -0.1(2) ?
C11 C12 C13 C8 . . . . -0.9(2) ?
C9 C8 C13 C12 . . . . 1.3(2) ?
S1 C8 C13 C12 . . . . -178.76(11) ?
C2 C1 N1 S1 . . . . -16.6(2) ?
C6 C1 N1 S1 . . . . 164.92(11) ?
C1 N1 S1 O1 . . . . 52.78(14) ?
C1 N1 S1 O2 . . . . -178.56(12) ?
C1 N1 S1 C8 . . . . -63.97(14) ?
C13 C8 S1 O1 . . . . -19.79(13) ?
C9 C8 S1 O1 . . . . 160.20(10) ?
C13 C8 S1 O2 . . . . -151.70(11) ?
C9 C8 S1 O2 . . . . 28.29(13) ?
C13 C8 S1 N1 . . . . 97.27(11) ?
C9 C8 S1 N1 . . . . -82.73(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743126
