#------------------------------------------------------------------------------
#$Date: 2019-10-28 09:23:29 +0200 (Mon, 28 Oct 2019) $
#$Revision: 219800 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/61/2226161.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_2226161
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Ellena, Javier'
'De Simone, Carlos A.'
'Ribeiro, Leandro'
'De Almeida Santos, Regina Helena'
_publ_section_title
;
 2-[(2-Carboxyphenyl)disulfanyl]benzoic acid--4,4'-bipyridyl
 N,N'-dioxide (1/2)
;
_journal_coeditor_code           HG2676
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1442
_journal_paper_doi               10.1107/S1600536810018775
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '2C14 H10 O4 S2, C10 H8 N2 O2'
_chemical_formula_moiety         '2(C14 H10 O4 S2), C10 H8 N2 O2'
_chemical_formula_sum            'C38 H28 N2 O10 S4'
_chemical_formula_weight         800.90
_chemical_name_systematic
;
2-[(2-Carboxyphenyl)disulfanyl]benzoic acid--4,4'-bipyridyl
N,N'-dioxide (1/2)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 105.412(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.314(2)
_cell_length_b                   10.5621(8)
_cell_length_c                   16.005(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    291
_cell_measurement_theta_max      19.14
_cell_measurement_theta_min      10.25
_cell_volume                     3473.5(18)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1993)
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1993)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al.,  2006)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.0(10)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku AFC-7S diffractometer'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_sigmaI/netI    0.006
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3066
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0.87
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.951
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.473
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_gt           0.065
_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)+(0.1415P)²+4.1121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.189
_refine_ls_wR_factor_ref         0.192
_reflns_number_gt                2658
_reflns_number_total             2781
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2676.cif
_cod_data_source_block           I
_cod_depositor_comments
;

2019-10-23
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C19 H14 N O5 S2'
_cod_original_formula_weight         400.45
_cod_original_formula_moiety         'C14 H10 O4 S2, 0.5(C10 H8 N2 O2)'
_cod_original_formula_iupac          'C14 H10 O4 S2, 0.5C10 H8 N2 O2'
_cod_original_formula_units_Z            8
_cod_original_sg_symbol_Hall     '-c 2yc'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2226161
_cod_database_fobs_code          2226161
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'
'-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 S2 0.34651(3) 0.02160(7) 0.27473(5) 0.0381(3) Uani d . 1 . .
S S1 0.25516(3) -0.05076(8) 0.22805(5) 0.0389(3) Uani d . 1 . .
O O2 0.13221(10) -0.1328(3) 0.17027(17) 0.0487(6) Uani d . 1 . .
O O4 0.55073(13) 0.0281(3) 0.4215(2) 0.0761(9) Uani d . 1 . .
O O3 0.07037(11) -0.1051(3) 0.03538(17) 0.0589(7) Uani d . 1 . .
H H3 0.0408 -0.1159 0.0585 0.088 Uiso calc R 1 . .
O O5 0.46308(12) 0.1178(2) 0.3372(2) 0.0690(9) Uani d . 1 . .
H H55 0.4829 0.1832 0.3551 0.103 Uiso calc R 1 . .
C C13 0.39868(14) -0.1151(3) 0.2968(2) 0.0359(7) Uani d . 1 . .
C C17 0.41418(17) -0.3405(3) 0.2889(2) 0.0472(8) Uani d . 1 . .
H H17 0.3975 -0.4197 0.2693 0.057 Uiso calc R 1 . .
C C9 0.29901(14) -0.0579(3) 0.0790(2) 0.0374(7) Uani d . 1 . .
H H9 0.3401 -0.0404 0.1150 0.045 Uiso calc R 1 . .
C C7 0.18433(13) -0.0960(2) 0.0587(2) 0.0337(7) Uani d . 1 . .
C C14 0.46425(14) -0.1032(3) 0.3434(2) 0.0379(7) Uani d . 1 . .
C C11 0.23059(17) -0.0955(3) -0.0634(2) 0.0443(8) Uani d . 1 . .
H H11 0.2254 -0.1039 -0.1227 0.053 Uiso calc R 1 . .
C C8 0.24617(13) -0.0705(3) 0.1146(2) 0.0335(7) Uani d . 1 . .
C C10 0.29099(16) -0.0710(3) -0.0088(2) 0.0428(8) Uani d . 1 . .
H H10 0.3268 -0.0632 -0.0314 0.051 Uiso calc R 1 . .
C C18 0.37493(15) -0.2348(3) 0.2689(2) 0.0421(7) Uani d . 1 . .
H H18 0.3320 -0.2438 0.2363 0.051 Uiso calc R 1 . .
C C19 0.49747(14) 0.0205(3) 0.3733(2) 0.0441(8) Uani d . 1 . .
C C6 0.12735(14) -0.1140(3) 0.0947(2) 0.0395(8) Uani d . 1 . .
C C15 0.50222(15) -0.2117(3) 0.3643(2) 0.0455(8) Uani d . 1 . .
H H15 0.5452 -0.2041 0.3969 0.055 Uiso calc R 1 . .
C C16 0.47782(16) -0.3297(3) 0.3378(2) 0.0480(8) Uani d . 1 . .
H H16 0.5038 -0.4012 0.3527 0.058 Uiso calc R 1 . .
C C12 0.17762(15) -0.1077(3) -0.0295(2) 0.0422(8) Uani d . 1 . .
H H12 0.1368 -0.1239 -0.0665 0.051 Uiso calc R 1 . .
N N1 0.08340(11) 0.1895(2) 0.91617(17) 0.0361(6) Uani d . 1 . .
O O1 0.01985(9) 0.1677(2) 0.88364(16) 0.0460(6) Uani d . 1 . .
C C4 0.18672(14) 0.2206(3) 0.8937(2) 0.0399(7) Uani d . 1 . .
H H4 0.2127 0.2256 0.8555 0.048 Uiso calc R 1 . .
C C1 0.10782(14) 0.2062(3) 1.0006(2) 0.0449(8) Uani d . 1 . .
H H1 0.0804 0.2023 1.0371 0.054 Uiso calc R 1 . .
C C3 0.21476(12) 0.2373(2) 0.98169(19) 0.0311(6) Uani d . 1 . .
C C2 0.17312(14) 0.2295(3) 1.0351(2) 0.0436(8) Uani d . 1 . .
H H2 0.1895 0.2400 1.0946 0.052 Uiso calc R 1 . .
C C5 0.12157(14) 0.1970(3) 0.8619(2) 0.0428(7) Uani d . 1 . .
H H5 0.1038 0.1863 0.8027 0.051 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 3 0
7 3 1
6 2 3
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
C13 S2 S1 . . 104.55(10) ?
C8 S1 S2 . . 104.49(9) ?
C6 O3 H3 . . 109.5 ?
C19 O5 H55 . . 109.5 ?
C18 C13 C14 . . 118.6(3) ?
C18 C13 S2 . . 120.9(2) ?
C14 C13 S2 . . 120.6(2) ?
C16 C17 C18 . . 120.6(3) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
C10 C9 C8 . . 120.8(3) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C12 C7 C8 . . 119.3(3) ?
C12 C7 C6 . . 120.6(3) ?
C8 C7 C6 . . 120.1(3) ?
C15 C14 C13 . . 119.2(3) ?
C15 C14 C19 . . 116.4(3) ?
C13 C14 C19 . . 124.4(3) ?
C10 C11 C12 . . 119.5(3) ?
C10 C11 H11 . . 120.3 ?
C12 C11 H11 . . 120.3 ?
C9 C8 C7 . . 118.6(3) ?
C9 C8 S1 . . 121.5(2) ?
C7 C8 S1 . . 119.8(2) ?
C11 C10 C9 . . 120.6(3) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C17 C18 C13 . . 120.9(3) ?
C17 C18 H18 . . 119.5 ?
C13 C18 H18 . . 119.5 ?
O4 C19 O5 . . 123.9(3) ?
O4 C19 C14 . . 123.5(3) ?
O5 C19 C14 . . 112.5(3) ?
O2 C6 O3 . . 123.2(3) ?
O2 C6 C7 . . 123.3(3) ?
O3 C6 C7 . . 113.5(3) ?
C16 C15 C14 . . 121.7(3) ?
C16 C15 H15 . . 119.2 ?
C14 C15 H15 . . 119.2 ?
C15 C16 C17 . . 119.0(3) ?
C15 C16 H16 . . 120.5 ?
C17 C16 H16 . . 120.5 ?
C11 C12 C7 . . 121.2(3) ?
C11 C12 H12 . . 119.4 ?
C7 C12 H12 . . 119.4 ?
C1 N1 O1 . . 120.2(2) ?
C1 N1 C5 . . 120.7(3) ?
O1 N1 C5 . . 119.0(3) ?
C5 C4 C3 . . 121.4(3) ?
C5 C4 H4 . . 119.3 ?
C3 C4 H4 . . 119.3 ?
N1 C1 C2 . . 121.0(3) ?
N1 C1 H1 . . 119.5 ?
C2 C1 H1 . . 119.5 ?
C4 C3 C2 . . 116.3(3) ?
C4 C3 C3 . 7_557 122.8(3) ?
C2 C3 C3 . 7_557 120.9(3) ?
C1 C2 C3 . . 120.5(3) ?
C1 C2 H2 . . 119.8 ?
C3 C2 H2 . . 119.8 ?
N1 C5 C4 . . 120.0(3) ?
N1 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
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
S2 C13 . 1.799(3) ?
S2 S1 . 2.0397(10) ?
S1 C8 . 1.786(3) ?
O2 C6 . 1.203(4) ?
O4 C19 . 1.194(4) ?
O3 C6 . 1.331(4) ?
O3 H3 . 0.8200 ?
O5 C19 . 1.305(4) ?
O5 H55 . 0.8200 ?
C13 C18 . 1.391(4) ?
C13 C14 . 1.404(4) ?
C17 C16 . 1.379(5) ?
C17 C18 . 1.380(5) ?
C17 H17 . 0.9300 ?
C9 C10 . 1.376(5) ?
C9 C8 . 1.397(4) ?
C9 H9 . 0.9300 ?
C7 C12 . 1.386(5) ?
C7 C8 . 1.408(4) ?
C7 C6 . 1.488(4) ?
C14 C15 . 1.391(4) ?
C14 C19 . 1.502(4) ?
C11 C10 . 1.375(5) ?
C11 C12 . 1.383(5) ?
C11 H11 . 0.9300 ?
C10 H10 . 0.9300 ?
C18 H18 . 0.9300 ?
C15 C16 . 1.373(5) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C12 H12 . 0.9300 ?
N1 C1 . 1.324(4) ?
N1 O1 . 1.336(3) ?
N1 C5 . 1.340(4) ?
C4 C5 . 1.369(4) ?
C4 C3 . 1.387(5) ?
C4 H4 . 0.9300 ?
C1 C2 . 1.376(4) ?
C1 H1 . 0.9300 ?
C3 C2 . 1.389(4) ?
C3 C3 7_557 1.484(5) ?
C2 H2 . 0.9300 ?
C5 H5 . 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
O5 H55 O1 8 0.82 1.77 2.583(3) 173.8
O3 H3 O1 5_556 0.82 1.86 2.672(3) 170.1
O5 H55 N1 8 0.82 2.50 3.255(3) 153.9
C17 H17 O2 4_545 0.93 2.59 3.359(4) 139.8
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
C13 S2 S1 C8 . . . . -86.15(14) ?
S1 S2 C13 C18 . . . . 10.1(3) ?
S1 S2 C13 C14 . . . . -169.3(2) ?
C18 C13 C14 C15 . . . . -3.6(5) ?
S2 C13 C14 C15 . . . . 175.9(2) ?
C18 C13 C14 C19 . . . . 176.5(3) ?
S2 C13 C14 C19 . . . . -4.1(4) ?
C10 C9 C8 C7 . . . . -0.5(4) ?
C10 C9 C8 S1 . . . . -178.8(2) ?
C12 C7 C8 C9 . . . . -0.1(4) ?
C6 C7 C8 C9 . . . . 178.1(3) ?
C12 C7 C8 S1 . . . . 178.2(2) ?
C6 C7 C8 S1 . . . . -3.6(4) ?
S2 S1 C8 C9 . . . . 10.4(2) ?
S2 S1 C8 C7 . . . . -167.9(2) ?
C12 C11 C10 C9 . . . . -0.3(5) ?
C8 C9 C10 C11 . . . . 0.7(5) ?
C16 C17 C18 C13 . . . . 0.5(5) ?
C14 C13 C18 C17 . . . . 2.2(5) ?
S2 C13 C18 C17 . . . . -177.2(3) ?
C15 C14 C19 O4 . . . . -9.3(5) ?
C13 C14 C19 O4 . . . . 170.6(4) ?
C15 C14 C19 O5 . . . . 167.4(3) ?
C13 C14 C19 O5 . . . . -12.7(5) ?
C12 C7 C6 O2 . . . . 163.0(3) ?
C8 C7 C6 O2 . . . . -15.1(4) ?
C12 C7 C6 O3 . . . . -18.1(4) ?
C8 C7 C6 O3 . . . . 163.8(3) ?
C13 C14 C15 C16 . . . . 2.3(5) ?
C19 C14 C15 C16 . . . . -177.7(3) ?
C14 C15 C16 C17 . . . . 0.4(5) ?
C18 C17 C16 C15 . . . . -1.9(5) ?
C10 C11 C12 C7 . . . . -0.2(5) ?
C8 C7 C12 C11 . . . . 0.4(4) ?
C6 C7 C12 C11 . . . . -177.7(3) ?
O1 N1 C1 C2 . . . . -179.6(3) ?
C5 N1 C1 C2 . . . . -1.3(5) ?
C5 C4 C3 C2 . . . . -0.4(4) ?
C5 C4 C3 C3 . . . 7_557 179.8(3) ?
N1 C1 C2 C3 . . . . 0.8(5) ?
C4 C3 C2 C1 . . . . 0.1(5) ?
C3 C3 C2 C1 7_557 . . . 179.8(3) ?
C1 N1 C5 C4 . . . . 0.9(5) ?
O1 N1 C5 C4 . . . . 179.3(3) ?
C3 C4 C5 N1 . . . . -0.1(5) ?
