##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1841479'
_audit_creation_method     SHELXL-2014
_journal_date_recd_electronic     2018-04-16
_journal_date_accepted     2018-05-04
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2018
_journal_volume     74
_journal_issue      6
_journal_page_first     820
_journal_page_last     824
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989018006916
_journal_coeditor_code     YK2114
_publ_contact_author_name     'Thomas Albrecht-Schmitt'
_publ_contact_author_address
;
Department of Chemistry and Biochemistry, Florida State University,
95 Chieftan Way Tallahassee, FL 32306, USA
;
_publ_contact_author_email     'albrecht-schmitt@chem.fsu.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
A rare positively charged nicotinic acid disulfide: 2,2'-dithiodinicotinic acid
hydrochloride monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Chemey, Alexander T.' .
;
Department of Chemistry and Biochemistry, Florida State University,
95 Chieftan Way Tallahassee, FL 32306, USA
;
    'McGuire, Chad M.' .
;
Department of Chemistry and Biochemistry, Florida State University,
95 Chieftan Way Tallahassee, FL 32306, USA
;
    'Albrecht-Schmitt, Thomas E.' .
;
Department of Chemistry and Biochemistry, Florida State University,
95 Chieftan Way Tallahassee, FL 32306, USA
;
_publ_section_synopsis
;
An unexpected product was obtained from slow evaporation in acidic media, as a
protonated nitrogen is combined with a disulfide bond between a pair of
2-mercaptonicotinic acid moieties.
;
_chemical_name_systematic
;
3-Carboxy-2-[2-(3-carboxypyridin-2-yl)disulfan-1-yl)]pyridin-1-ium chloride
monohydrate
;
_chemical_name_common
;
2,2'-Dithiodinicotinic acid hydrochloride monohydrate
;
_chemical_formula_moiety     'C12 H9 N2 O4 S2 +, Cl -, H2 O'
_chemical_formula_sum     'C12 H11 Cl N2 O5 S2'
_chemical_formula_iupac     'C12 H9 N2 O4 S2 +, Cl -, H2 O'
_chemical_formula_weight     362.80
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.9906(12)
_cell_length_b     9.7081(14)
_cell_length_c     10.2704(15)
_cell_angle_alpha     86.727(3)
_cell_angle_beta     73.088(3)
_cell_angle_gamma     73.538(3)
_cell_volume     730.73(19)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2974
_cell_measurement_theta_min     2.775
_cell_measurement_theta_max     27.873
_cell_measurement_temperature     120(2)
_exptl_crystal_description     'truncated column'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.050
_exptl_crystal_size_mid     0.050
_exptl_crystal_size_min     0.030
_exptl_crystal_density_diffrn     1.649
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     372
_exptl_absorpt_coefficient_mu     0.572
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_shelx_estimated_absorpt_T_min     0.972
_shelx_estimated_absorpt_T_max     0.983
_exptl_absorpt_correction_T_min     0.6883
_exptl_absorpt_correction_T_max     0.7468
_exptl_special_details     ?
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker D8 Quest'
_diffrn_measurement_method     '0.5° wide /w exposures'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11750
_diffrn_reflns_av_R_equivalents     0.0312
_diffrn_reflns_theta_min     2.775
_diffrn_reflns_theta_max     27.873
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_decay_%     0
_refine_special_details     ?
_reflns_number_total     3483
_reflns_number_gt     2974
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0412
_refine_ls_R_factor_gt     0.0319
_refine_ls_wR_factor_gt     0.0712
_refine_ls_wR_factor_ref     0.0746
_refine_ls_goodness_of_fit_ref     1.064
_refine_ls_restrained_S_all     1.064
_refine_ls_number_reflns     3483
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0280P)²+0.4761P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.342
_refine_diff_density_min     -0.285
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX3 (Bruker, 2015)
;
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_reduction
;
SAINT (Bruker, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
SHELXP2014 (Sheldrick, 2015) and
VESTA (Momma & Izumi, 2011)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.55285(6) 0.73261(4) -0.03978(4) 0.01593(10) Uani d 1 . .
    S S2 0.34334(6) 0.84956(5) 0.11499(4) 0.01655(10) Uani d 1 . .
    O O4 1.03798(18) 0.38461(14) -0.23492(13) 0.0231(3) Uani d 1 . .
    N N1 0.6456(2) 0.88005(16) 0.15917(15) 0.0183(3) Uani d 1 . .
    O O3 0.81335(18) 0.58125(14) -0.24563(12) 0.0241(3) Uani d 1 . .
    O O2 0.09614(18) 1.16658(15) 0.45610(14) 0.0249(3) Uani d 1 . .
    C C12 0.8861(2) 0.48353(18) -0.18308(17) 0.0160(3) Uani d 1 . .
    N N2 0.5831(2) 0.55966(15) 0.17321(14) 0.0137(3) Uani d 1 . .
    H H2A 0.495(3) 0.625(3) 0.219(2) 0.033(6) Uiso d 1 . .
    O O1 0.07437(17) 1.04648(14) 0.28410(14) 0.0243(3) Uani d 1 . .
    C C9 0.8823(2) 0.35342(18) 0.03531(18) 0.0164(3) Uani d 1 . .
    H H9A 0.987(3) 0.286(2) -0.013(2) 0.015(5) Uiso d 1 . .
    C C10 0.8052(2) 0.33966(19) 0.17376(18) 0.0181(4) Uani d 1 . .
    H H10 0.854(3) 0.263(2) 0.220(2) 0.022(5) Uiso d 1 . .
    C C11 0.6531(2) 0.44517(19) 0.24083(18) 0.0169(3) Uani d 1 . .
    H H11 0.596(3) 0.443(2) 0.334(2) 0.016(5) Uiso d 1 . .
    C C5 0.7374(2) 0.93776(19) 0.22147(19) 0.0196(4) Uani d 1 . .
    H H5A 0.869(3) 0.901(2) 0.192(2) 0.021(5) Uiso d 1 . .
    C C7 0.6516(2) 0.57744(17) 0.03867(16) 0.0129(3) Uani d 1 . .
    C C1 0.4649(2) 0.92968(17) 0.19882(17) 0.0148(3) Uani d 1 . .
    C C4 0.6562(2) 1.04237(18) 0.32312(18) 0.0174(3) Uani d 1 . .
    H H4A 0.723(3) 1.075(2) 0.364(2) 0.025(6) Uiso d 1 . .
    C C3 0.4674(2) 1.09120(18) 0.36465(17) 0.0160(3) Uani d 1 . .
    H H3A 0.408(3) 1.162(2) 0.430(2) 0.014(5) Uiso d 1 . .
    C C2 0.3676(2) 1.03471(17) 0.30221(17) 0.0148(3) Uani d 1 . .
    C C8 0.8054(2) 0.46990(17) -0.03376(16) 0.0139(3) Uani d 1 . .
    C C6 0.1649(2) 1.08231(18) 0.34541(18) 0.0168(3) Uani d 1 . .
    H H4 1.093(4) 0.396(3) -0.336(3) 0.058(8) Uiso d 1 . .
    H H3 -0.028(4) 1.198(3) 0.478(3) 0.059(9) Uiso d 1 . .
    O O5 1.20128(19) 1.41990(16) 0.52156(14) 0.0237(3) Uani d 1 . .
    H H1 1.173(4) 1.400(3) 0.453(3) 0.064(9) Uiso d 1 . .
    H H2 1.232(4) 1.501(3) 0.504(3) 0.062(9) Uiso d 1 . .
    Cl Cl1 0.68897(6) 1.29911(4) 0.55204(4) 0.01899(11) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    S1 C7 . 1.7602(17) ?
    S1 S2 . 2.0491(6) ?
    S2 C1 . 1.8113(17) ?
    O4 C12 . 1.304(2) ?
    O4 H4 . 1.01(3) ?
    N1 C1 . 1.330(2) ?
    N1 C5 . 1.345(2) ?
    O3 C12 . 1.219(2) ?
    O2 C6 . 1.324(2) ?
    O2 H3 . 0.91(3) ?
    C12 C8 . 1.495(2) ?
    N2 C11 . 1.348(2) ?
    N2 C7 . 1.351(2) ?
    N2 H2A . 0.84(2) ?
    O1 C6 . 1.214(2) ?
    C9 C8 . 1.388(2) ?
    C9 C10 . 1.391(2) ?
    C9 H9A . 0.93(2) ?
    C10 C11 . 1.374(3) ?
    C10 H10 . 0.91(2) ?
    C11 H11 . 0.94(2) ?
    C5 C4 . 1.377(3) ?
    C5 H5A . 0.97(2) ?
    C7 C8 . 1.408(2) ?
    C1 C2 . 1.402(2) ?
    C4 C3 . 1.388(2) ?
    C4 H4A . 0.90(2) ?
    C3 C2 . 1.390(2) ?
    C3 H3A . 0.912(19) ?
    C2 C6 . 1.489(2) ?
    O5 H1 . 0.85(3) ?
    O5 H2 . 0.88(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
    C7 S1 S2 . . 104.35(6) ?
    C1 S2 S1 . . 101.27(6) ?
    C12 O4 H4 . . 113.0(16) ?
    C1 N1 C5 . . 116.90(15) ?
    C6 O2 H3 . . 111.6(18) ?
    O3 C12 O4 . . 125.39(16) ?
    O3 C12 C8 . . 120.99(15) ?
    O4 C12 C8 . . 113.61(15) ?
    C11 N2 C7 . . 123.70(15) ?
    C11 N2 H2A . . 117.0(16) ?
    C7 N2 H2A . . 119.2(16) ?
    C8 C9 C10 . . 120.68(16) ?
    C8 C9 H9A . . 118.4(12) ?
    C10 C9 H9A . . 120.9(12) ?
    C11 C10 C9 . . 118.45(16) ?
    C11 C10 H10 . . 120.2(13) ?
    C9 C10 H10 . . 121.4(13) ?
    N2 C11 C10 . . 120.19(16) ?
    N2 C11 H11 . . 117.2(12) ?
    C10 C11 H11 . . 122.6(12) ?
    N1 C5 C4 . . 124.23(16) ?
    N1 C5 H5A . . 116.2(12) ?
    C4 C5 H5A . . 119.6(12) ?
    N2 C7 C8 . . 117.59(15) ?
    N2 C7 S1 . . 120.27(12) ?
    C8 C7 S1 . . 122.13(12) ?
    N1 C1 C2 . . 123.81(15) ?
    N1 C1 S2 . . 116.31(13) ?
    C2 C1 S2 . . 119.85(13) ?
    C5 C4 C3 . . 118.05(17) ?
    C5 C4 H4A . . 121.2(14) ?
    C3 C4 H4A . . 120.7(14) ?
    C4 C3 C2 . . 119.45(16) ?
    C4 C3 H3A . . 121.1(12) ?
    C2 C3 H3A . . 119.4(12) ?
    C3 C2 C1 . . 117.55(15) ?
    C3 C2 C6 . . 121.11(15) ?
    C1 C2 C6 . . 121.33(15) ?
    C9 C8 C7 . . 119.36(15) ?
    C9 C8 C12 . . 120.77(15) ?
    C7 C8 C12 . . 119.86(15) ?
    O1 C6 O2 . . 124.40(16) ?
    O1 C6 C2 . . 122.64(16) ?
    O2 C6 C2 . . 112.96(15) ?
    H1 O5 H2 . . 107(3) ?
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
    N2 H2A Cl1 2_676 0.84(2) 2.41(2) 3.1228(15) 143(2)
    C10 H10 O1 1_645 0.91(2) 2.53(2) 3.405(2) 162.0(18)
    C11 H11 Cl1 1_545 0.94(2) 2.74(2) 3.4776(18) 135.7(15)
    C4 H4A O1 1_655 0.90(2) 2.63(2) 3.259(2) 128.5(17)
    C4 H4A Cl1 . 0.90(2) 2.89(2) 3.6340(19) 141.1(17)
    O4 H4 O5 1_544 1.01(3) 1.52(3) 2.5164(19) 169(3)
    O2 H3 Cl1 1_455 0.91(3) 2.12(3) 3.0197(15) 170(3)
    O5 H1 O3 2_775 0.85(3) 2.10(3) 2.8709(19) 151(3)
    O5 H2 Cl1 2_786 0.88(3) 2.20(3) 3.0848(16) 177(3)
_shelxl_version_number        2.014
