#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/83/2218362.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_2218362
loop_
_publ_author_name
'Zhang, Xinli'
'Li, Zongxiao'
_publ_section_title
;
 (E)-4-[(2-Hydroxybenzylidene)amino]benzenesulfonic acid
;
_journal_coeditor_code           CI2596
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1159
_journal_paper_doi               10.1107/S1600536808015407
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C13 H11 N O4 S'
_chemical_formula_moiety         'C13 H11 N O4 S'
_chemical_formula_sum            'C13 H11 N O4 S'
_chemical_formula_weight         277.29
_chemical_name_systematic
;
(E)-4-[(2-Hydroxybenzylidene)amino]benzenesulfonic acid
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.223(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8711(5)
_cell_length_b                   29.022(3)
_cell_length_c                   9.0356(17)
_cell_measurement_reflns_used    1329
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.9
_cell_measurement_theta_min      2.671
_cell_volume                     1267.2(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3185
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.9614
_exptl_absorpt_correction_T_min  0.8970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.301
_refine_ls_abs_structure_details 'Flack (1983), 822 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.06(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         1952
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0495
_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)+(0.0495P)²+1.7913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1207
_reflns_number_gt                1656
_reflns_number_total             1952
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2596.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'C c'
_cod_database_code               2218362
_cod_database_fobs_code          2218362
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, 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 0.75870(18) 0.76105(3) 0.47671(13) 0.0372(3) Uani d . 1 B .
N N1 0.6129(9) 0.96320(13) 0.4070(4) 0.0490(10) Uani d . 1 B .
O O1 0.6035(6) 0.73963(10) 0.3515(3) 0.0470(8) Uani d . 1 . .
O O2 0.6306(8) 0.74475(13) 0.6247(5) 0.0663(11) Uani d . 1 . .
H H2 0.4678 0.7526 0.6185 0.099 Uiso calc R 1 . .
O O3 1.0490(7) 0.75204(11) 0.5021(4) 0.0501(8) Uani d . 1 . .
O O4 0.387(2) 1.0337(3) 0.2463(11) 0.0675(18) Uani d P 0.528(8) A 1
H H4 0.4579 1.0080 0.2483 0.101 Uiso calc PR 0.528(8) A 1
O O4' 0.285(2) 1.0279(4) 0.3133(12) 0.0675(18) Uani d P 0.472(8) A 2
H H4' 0.3138 1.0031 0.3557 0.101 Uiso calc PR 0.472(8) A 2
C C1 0.7196(9) 0.82135(14) 0.4573(5) 0.0365(11) Uani d . 1 . .
C C2 0.585(3) 0.8377(3) 0.3264(16) 0.042(3) Uani d P 0.510(16) B 1
H H2A 0.5178 0.8179 0.2493 0.051 Uiso calc PR 0.510(16) B 1
C C3 0.554(3) 0.8837(3) 0.3133(16) 0.045(3) Uani d P 0.510(16) B 1
H H3 0.4598 0.8955 0.2254 0.055 Uiso calc PR 0.510(16) B 1
C C2' 0.470(3) 0.8413(3) 0.3925(16) 0.042(3) Uani d P 0.490(16) B 2
H H2' 0.3224 0.8223 0.3586 0.051 Uiso calc PR 0.490(16) B 2
C C3' 0.439(3) 0.8887(3) 0.3777(16) 0.044(3) Uani d P 0.490(16) B 2
H H3' 0.2733 0.9015 0.3339 0.053 Uiso calc PR 0.490(16) B 2
C C4 0.6589(11) 0.91570(17) 0.4298(6) 0.0426(11) Uani d . 1 . .
C C5 0.805(3) 0.8949(4) 0.5579(16) 0.046(3) Uani d P 0.510(16) B 1
H H5 0.8868 0.9136 0.6346 0.056 Uiso calc PR 0.510(16) B 1
C C6 0.829(3) 0.8473(4) 0.5726(16) 0.043(3) Uani d P 0.510(16) B 1
H H6 0.9179 0.8339 0.6592 0.052 Uiso calc PR 0.510(16) B 1
C C5' 0.909(3) 0.8993(4) 0.4909(19) 0.047(3) Uani d P 0.490(16) B 2
H H5' 1.0547 0.9193 0.5213 0.056 Uiso calc PR 0.490(16) B 2
C C6' 0.941(3) 0.8522(4) 0.5065(17) 0.047(3) Uani d P 0.490(16) B 2
H H6' 1.1100 0.8403 0.5497 0.057 Uiso calc PR 0.490(16) B 2
C C7 0.7682(15) 0.99282(16) 0.4771(9) 0.0655(13) Uani d . 1 . .
H H7 0.9180 0.9826 0.5429 0.079 Uiso calc R 1 B .
C C8 0.7245(14) 1.04208(16) 0.4601(8) 0.0570(14) Uani d . 1 A .
C C9 0.5144(14) 1.0594(2) 0.3606(8) 0.0771(19) Uani d . 1 . .
C C10 0.488(2) 1.1068(2) 0.3501(10) 0.107(3) Uani d . 1 A .
H H10 0.3437 1.1187 0.2843 0.129 Uiso calc R 1 . .
C C11 0.6584(18) 1.1363(2) 0.4287(9) 0.0768(18) Uani d . 1 . .
H H11 0.6321 1.1679 0.4172 0.092 Uiso calc R 1 A .
C C12 0.863(2) 1.1202(2) 0.5224(11) 0.102(3) Uani d . 1 A .
H H12 0.9840 1.1404 0.5776 0.122 Uiso calc R 1 . .
C C13 0.8992(19) 1.0729(2) 0.5393(10) 0.111(3) Uani d . 1 . .
H H13 1.0455 1.0618 0.6059 0.133 Uiso calc R 1 A .
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
O1 S1 O3 117.6(2)
O1 S1 O2 108.0(2)
O3 S1 O2 106.9(2)
O1 S1 C1 108.29(19)
O3 S1 C1 106.8(2)
O2 S1 C1 108.9(2)
C7 N1 C4 121.3(4)
S1 O2 H2 109.5
C9 O4 H4 109.5
C9 O4' H4' 109.5
C6 C1 C2 125.4(8)
C6 C1 C2' 109.3(8)
C2 C1 C6' 108.3(7)
C2' C1 C6' 116.8(7)
C6 C1 S1 116.8(6)
C2 C1 S1 117.7(5)
C2' C1 S1 121.8(5)
C6' C1 S1 121.4(5)
C3 C2 C1 117.3(10)
C3 C2 H2A 121.4
C1 C2 H2A 121.4
C2 C3 C4 123.0(10)
C2 C3 H3 118.5
C4 C3 H3 118.5
C3' C2' C1 121.9(9)
C3' C2' H2' 119.0
C1 C2' H2' 119.0
C4 C3' C2' 117.6(10)
C4 C3' H3' 121.2
C2' C3' H3' 121.2
C5' C4 C3' 124.4(8)
C5' C4 N1 121.3(6)
C3' C4 N1 114.1(6)
C3' C4 C5 109.2(8)
N1 C4 C5 126.3(6)
C5' C4 C3 106.8(8)
N1 C4 C3 119.1(6)
C5 C4 C3 114.6(7)
C6 C5 C4 122.0(10)
C6 C5 H5 119.0
C4 C5 H5 119.0
C1 C6 C5 117.5(10)
C1 C6 H6 121.2
C5 C6 H6 121.2
C4 C5' C6' 118.2(11)
C4 C5' H5' 120.9
C6' C5' H5' 120.9
C5' C6' C1 121.1(11)
C5' C6' H6' 119.5
C1 C6' H6' 119.5
N1 C7 C8 123.2(6)
N1 C7 H7 118.4
C8 C7 H7 118.4
C9 C8 C13 117.8(6)
C9 C8 C7 121.3(6)
C13 C8 C7 120.9(6)
O4 C9 C8 121.9(6)
O4 C9 C10 117.7(7)
C8 C9 C10 117.7(6)
C8 C9 O4' 116.2(6)
C10 C9 O4' 122.7(7)
C11 C10 C9 123.8(7)
C11 C10 H10 118.1
C9 C10 H10 118.1
C12 C11 C10 119.1(7)
C12 C11 H11 120.5
C10 C11 H11 120.5
C11 C12 C13 119.9(8)
C11 C12 H12 120.0
C13 C12 H12 120.0
C8 C13 C12 121.7(8)
C8 C13 H13 119.2
C12 C13 H13 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.422(3)
S1 O3 1.428(3)
S1 O2 1.615(4)
S1 C1 1.767(4)
N1 C7 1.262(7)
N1 C4 1.408(6)
O2 H2 0.82
O4 C9 1.359(10)
O4 H4 0.82
O4' C9 1.465(12)
O4' H4' 0.82
C1 C6 1.340(11)
C1 C2 1.363(12)
C1 C2' 1.405(12)
C1 C6' 1.430(13)
C2 C3 1.348(13)
C2 H2A 0.93
C3 C4 1.448(13)
C3 H3 0.93
C2' C3' 1.387(14)
C2' H2' 0.93
C3' C4 1.364(12)
C3' H3' 0.93
C4 C5' 1.359(15)
C4 C5 1.415(14)
C5 C6 1.392(15)
C5 H5 0.93
C6 H6 0.93
C5' C6' 1.382(15)
C5' H5' 0.93
C6' H6' 0.93
C7 C8 1.451(6)
C7 H7 0.93
C8 C9 1.370(8)
C8 C13 1.372(9)
C9 C10 1.382(8)
C10 C11 1.333(11)
C10 H10 0.93
C11 C12 1.310(10)
C11 H11 0.93
C12 C13 1.390(9)
C12 H12 0.93
C13 H13 0.93
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
O2 H2 O3 1_455 0.82 2.17 2.917(5) 151
O4 H4 N1 . 0.82 2.01 2.665(10) 136
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
O1 S1 C1 C6 173.5(9)
O3 S1 C1 C6 -58.9(9)
O2 S1 C1 C6 56.3(9)
O1 S1 C1 C2 -7.4(9)
O3 S1 C1 C2 120.2(8)
O2 S1 C1 C2 -124.6(8)
O1 S1 C1 C2' 35.0(9)
O3 S1 C1 C2' 162.6(8)
O2 S1 C1 C2' -82.2(9)
O1 S1 C1 C6' -144.8(9)
O3 S1 C1 C6' -17.2(9)
O2 S1 C1 C6' 98.0(9)
C6 C1 C2 C3 -1.7(17)
C2' C1 C2 C3 72.3(14)
C6' C1 C2 C3 -38.2(14)
S1 C1 C2 C3 179.3(9)
C1 C2 C3 C4 1.0(18)
C6 C1 C2' C3' 38.5(15)
C2 C1 C2' C3' -85.4(15)
C6' C1 C2' C3' -0.5(16)
S1 C1 C2' C3' 179.7(9)
C1 C2' C3' C4 -0.6(17)
C2' C3' C4 C5' 2.1(17)
C2' C3' C4 N1 178.4(9)
C2' C3' C4 C5 -34.2(14)
C2' C3' C4 C3 71.5(13)
C7 N1 C4 C5' -19.9(12)
C7 N1 C4 C3' 163.7(9)
C7 N1 C4 C5 22.8(12)
C7 N1 C4 C3 -156.4(9)
C2 C3 C4 C5' 38.7(16)
C2 C3 C4 C3' -87.5(16)
C2 C3 C4 N1 -179.1(10)
C2 C3 C4 C5 1.5(17)
C5' C4 C5 C6 -88.1(15)
C3' C4 C5 C6 34.7(15)
N1 C4 C5 C6 177.2(9)
C3 C4 C5 C6 -3.6(16)
C2 C1 C6 C5 -0.2(17)
C2' C1 C6 C5 -37.8(14)
C6' C1 C6 C5 71.4(15)
S1 C1 C6 C5 178.8(9)
C4 C5 C6 C1 3.0(18)
C3' C4 C5' C6' -2.4(19)
N1 C4 C5' C6' -178.4(10)
C5 C4 C5' C6' 71.8(15)
C3 C4 C5' C6' -37.3(15)
C4 C5' C6' C1 1(2)
C6 C1 C6' C5' -86.4(17)
C2 C1 C6' C5' 39.1(16)
C2' C1 C6' C5' 0.2(17)
S1 C1 C6' C5' 180.0(10)
C4 N1 C7 C8 -178.4(6)
N1 C7 C8 C9 -2.7(11)
N1 C7 C8 C13 179.9(8)
C13 C8 C9 O4 159.1(9)
C7 C8 C9 O4 -18.5(11)
C13 C8 C9 C10 -1.8(11)
C7 C8 C9 C10 -179.4(8)
C13 C8 C9 O4' -161.6(8)
C7 C8 C9 O4' 20.9(11)
O4 C9 C10 C11 -160.3(10)
C8 C9 C10 C11 1.4(14)
O4' C9 C10 C11 159.7(10)
C9 C10 C11 C12 -0.2(15)
C10 C11 C12 C13 -0.4(14)
C9 C8 C13 C12 1.3(13)
C7 C8 C13 C12 178.9(9)
C11 C12 C13 C8 -0.2(14)
