#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/24/2222414.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_2222414
loop_
_publ_author_name
'Sun, Shu-Wen'
'Zhou, Fu-Lin'
'Wang, Gao-Feng'
'Cui, Gui-Hua'
_publ_section_title
;
 6,6'-Dihydroxy-3,3'-dithiodibenzoic acid
;
_journal_coeditor_code           NG2599
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1701
_journal_paper_doi               10.1107/S1600536809023757
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H10 O6 S2'
_chemical_formula_moiety         'C14 H10 O6 S2'
_chemical_formula_sum            'C14 H10 O6 S2'
_chemical_formula_weight         338.34
_chemical_melting_point          523
_chemical_name_common            '5,5'-dithiodisalicylic acid'
_chemical_name_systematic
;
6,6'-Dihydroxy-3,3'-dithiodibenzoic acid
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3065(6)
_cell_length_b                   11.1657(13)
_cell_length_c                   23.906(2)
_cell_measurement_reflns_used    2489
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.478
_cell_measurement_theta_min      2.498
_cell_volume                     1416.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 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  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            6436
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.70
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_T_max  0.9458
_exptl_absorpt_correction_T_min  0.9095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.282
_refine_ls_abs_structure_details 'Flack (1983), 1007 Friedel pairs'
_refine_ls_abs_structure_Flack   0.49(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2502
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0448
_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)+(0.0345P)²+0.9484P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1027
_reflns_number_gt                2060
_reflns_number_total             2502
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2599.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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_cell_volume        1416.5(3)
_cod_database_code               2222414
_cod_database_fobs_code          2222414
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O O1 -0.4934(6) 0.8216(2) 0.21892(11) 0.0439(7) Uani d . 1 . .
O O2 -0.6036(6) 0.6399(3) 0.18732(11) 0.0439(8) Uani d D 1 . .
H H2 -0.717(6) 0.643(4) 0.2123(14) 0.066 Uiso d D 1 . .
O O3 -0.1299(6) 0.9391(3) 0.16941(13) 0.0519(8) Uani d D 1 . .
H H3 -0.254(6) 0.934(5) 0.1911(17) 0.078 Uiso d D 1 . .
O O4 -0.1551(7) 0.3528(3) 0.20456(12) 0.0505(8) Uani d D 1 . .
H H4 -0.269(7) 0.338(4) 0.2286(15) 0.076 Uiso d D 1 . .
O O5 -0.0215(6) 0.1743(3) 0.23556(11) 0.0438(7) Uani d . 1 . .
O O6 0.3765(6) 0.0759(3) 0.18767(12) 0.0503(8) Uani d D 1 . .
H H6 0.252(6) 0.080(5) 0.2099(17) 0.075 Uiso d D 1 . .
S S1 -0.0244(2) 0.52404(9) 0.01641(4) 0.0370(3) Uani d . 1 . .
S S2 0.34345(19) 0.46809(9) 0.01989(4) 0.0360(2) Uani d . 1 . .
C C1 -0.4622(8) 0.7376(4) 0.18627(14) 0.0343(9) Uani d . 1 . .
C C2 -0.2645(7) 0.7386(3) 0.14288(15) 0.0303(9) Uani d . 1 . .
C C3 -0.1095(8) 0.8396(3) 0.13723(15) 0.0360(10) Uani d . 1 . .
C C4 0.0804(8) 0.8402(4) 0.09698(16) 0.0391(10) Uani d . 1 . .
H H4A 0.1880 0.9057 0.0942 0.047 Uiso calc R 1 . .
C C5 0.1095(8) 0.7447(3) 0.06154(16) 0.0391(10) Uani d . 1 . .
H H5 0.2337 0.7470 0.0341 0.047 Uiso calc R 1 . .
C C6 -0.0443(8) 0.6441(3) 0.06607(15) 0.0324(9) Uani d . 1 . .
C C7 -0.2280(8) 0.6406(3) 0.10693(15) 0.0339(9) Uani d . 1 . .
H H7 -0.3285 0.5729 0.1107 0.041 Uiso calc R 1 . .
C C8 -0.0058(8) 0.2582(4) 0.20199(16) 0.0367(9) Uani d . 1 . .
C C9 0.1795(7) 0.2604(3) 0.15645(15) 0.0314(9) Uani d . 1 . .
C C10 0.3593(8) 0.1685(3) 0.15118(15) 0.0356(9) Uani d . 1 . .
C C11 0.5317(8) 0.1726(3) 0.10729(16) 0.0404(10) Uani d . 1 . .
H H11 0.6534 0.1130 0.1041 0.048 Uiso calc R 1 . .
C C12 0.5236(8) 0.2640(3) 0.06854(16) 0.0387(9) Uani d . 1 . .
H H12 0.6396 0.2651 0.0394 0.046 Uiso calc R 1 . .
C C13 0.3440(8) 0.3550(3) 0.07246(14) 0.0312(9) Uani d . 1 . .
C C14 0.1790(8) 0.3533(3) 0.11681(15) 0.0350(9) Uani d . 1 . .
H H14 0.0637 0.4155 0.1207 0.042 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'
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
C1 O2 H2 . . 113(3) ?
C3 O3 H3 . . 111(4) ?
C8 O4 H4 . . 108(4) ?
C10 O6 H6 . . 108(4) ?
C6 S1 S2 . . 104.89(14) yes
C13 S2 S1 . . 104.24(14) yes
O1 C1 O2 . . 122.6(4) ?
O1 C1 C2 . . 122.4(4) ?
O2 C1 C2 . . 115.0(3) ?
C3 C2 C7 . . 119.1(3) ?
C3 C2 C1 . . 119.4(3) ?
C7 C2 C1 . . 121.5(3) ?
O3 C3 C4 . . 116.4(4) ?
O3 C3 C2 . . 123.9(4) ?
C4 C3 C2 . . 119.6(4) ?
C5 C4 C3 . . 120.3(4) ?
C5 C4 H4A . . 119.9 ?
C3 C4 H4A . . 119.9 ?
C4 C5 C6 . . 120.9(4) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 119.4(3) ?
C7 C6 S1 . . 119.3(3) ?
C5 C6 S1 . . 121.1(3) ?
C6 C7 C2 . . 120.6(4) ?
C6 C7 H7 . . 119.7 ?
C2 C7 H7 . . 119.7 ?
O5 C8 O4 . . 122.4(4) ?
O5 C8 C9 . . 122.7(4) ?
O4 C8 C9 . . 115.0(4) ?
C14 C9 C10 . . 118.6(3) ?
C14 C9 C8 . . 120.8(4) ?
C10 C9 C8 . . 120.6(3) ?
O6 C10 C11 . . 117.7(4) ?
O6 C10 C9 . . 123.0(3) ?
C11 C10 C9 . . 119.3(4) ?
C12 C11 C10 . . 120.6(4) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C11 C12 C13 . . 121.0(4) ?
C11 C12 H12 . . 119.5 ?
C13 C12 H12 . . 119.5 ?
C14 C13 C12 . . 118.4(4) ?
C14 C13 S2 . . 123.6(3) ?
C12 C13 S2 . . 118.0(3) ?
C13 C14 C9 . . 121.9(4) ?
C13 C14 H14 . . 119.0 ?
C9 C14 H14 . . 119.0 ?
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
O1 C1 . 1.231(4) ?
O2 C1 . 1.324(5) ?
O2 H2 . 0.848(10) ?
O3 C3 . 1.356(5) ?
O3 H3 . 0.842(10) ?
O4 C8 . 1.322(5) ?
O4 H4 . 0.848(10) ?
O5 C8 . 1.236(5) ?
O6 C10 . 1.356(4) ?
O6 H6 . 0.849(10) ?
S1 C6 . 1.793(4) yes
S1 S2 . 2.0511(15) yes
S2 C13 . 1.781(4) yes
C1 C2 . 1.476(5) ?
C2 C3 . 1.402(5) ?
C2 C7 . 1.404(5) ?
C3 C4 . 1.394(5) ?
C4 C5 . 1.371(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.393(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.380(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.467(5) ?
C9 C14 . 1.405(5) ?
C9 C10 . 1.407(6) ?
C10 C11 . 1.393(5) ?
C11 C12 . 1.380(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.396(5) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.375(5) ?
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
O2 H2 O5 3_455 0.85(3) 1.90(3) 2.739(4) 171(4) yes
O3 H3 O1 . 0.84(4) 1.91(5) 2.616(4) 142(5) yes
O3 H3 O6 1_465 0.84(4) 2.52(4) 3.063(5) 123(4) yes
O4 H4 O1 3_445 0.85(4) 1.79(4) 2.636(4) 175(4) yes
O6 H6 O5 . 0.85(4) 1.90(4) 2.642(4) 146(5) 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
C6 S1 S2 C13 . . . . 89.96(17) yes
O1 C1 C2 C3 . . . . -1.7(5) ?
O2 C1 C2 C3 . . . . 178.1(3) ?
O1 C1 C2 C7 . . . . 178.4(4) ?
O2 C1 C2 C7 . . . . -1.7(5) ?
C7 C2 C3 O3 . . . . 179.5(3) ?
C1 C2 C3 O3 . . . . -0.3(6) ?
C7 C2 C3 C4 . . . . -1.3(6) ?
C1 C2 C3 C4 . . . . 178.9(3) ?
O3 C3 C4 C5 . . . . -178.1(4) ?
C2 C3 C4 C5 . . . . 2.7(6) ?
C3 C4 C5 C6 . . . . -1.9(6) ?
C4 C5 C6 C7 . . . . -0.2(6) ?
C4 C5 C6 S1 . . . . 174.9(3) ?
S2 S1 C6 C7 . . . . -127.2(3) ?
S2 S1 C6 C5 . . . . 57.7(3) ?
C5 C6 C7 C2 . . . . 1.5(6) ?
S1 C6 C7 C2 . . . . -173.7(3) ?
C3 C2 C7 C6 . . . . -0.8(6) ?
C1 C2 C7 C6 . . . . 179.0(3) ?
O5 C8 C9 C14 . . . . 175.4(4) ?
O4 C8 C9 C14 . . . . -4.7(5) ?
O5 C8 C9 C10 . . . . -3.8(6) ?
O4 C8 C9 C10 . . . . 176.1(4) ?
C14 C9 C10 O6 . . . . 179.2(4) ?
C8 C9 C10 O6 . . . . -1.6(6) ?
C14 C9 C10 C11 . . . . 0.4(6) ?
C8 C9 C10 C11 . . . . 179.5(4) ?
O6 C10 C11 C12 . . . . 179.7(4) ?
C9 C10 C11 C12 . . . . -1.4(6) ?
C10 C11 C12 C13 . . . . 0.4(6) ?
C11 C12 C13 C14 . . . . 1.8(6) ?
C11 C12 C13 S2 . . . . -178.8(3) ?
S1 S2 C13 C14 . . . . -29.0(3) ?
S1 S2 C13 C12 . . . . 151.6(3) ?
C12 C13 C14 C9 . . . . -2.9(6) ?
S2 C13 C14 C9 . . . . 177.8(3) ?
C10 C9 C14 C13 . . . . 1.8(6) ?
C8 C9 C14 C13 . . . . -177.4(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 81766
