#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/50/2015094.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_2015094
loop_
_publ_author_name
'Graham Smith'
'Urs D. Wermuth'
'Peter C. Healy'
_publ_section_title
;
 Layered structures in proton-transfer compounds of 5-sulfosalicylic
 acid with the aromatic polyamines 2,6-diaminopyridine and
 1,4-phenylenediamine
;
_journal_coeditor_code           TA1503
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o555
_journal_page_last               o558
_journal_paper_doi               10.1107/S010827010502439X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C6 H10 N2 2+, C7 H4 O6 S 2-'
_chemical_formula_moiety         'C6 H10 N2 2+, C7 H4 O6 S 2-'
_chemical_formula_sum            'C13 H14 N2 O6 S'
_chemical_formula_weight         326.32
_chemical_melting_point          ' greater than 555 K '
_chemical_name_common            '1,4-phenylenediaminium 5-sulfosalicylate'
_chemical_name_systematic
;
1,4-phenylenediaminium 3-carboxylato-4-hydroxybenzenesolfonate
;
_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           'SHELXL97 (Sheldrick, 1997)'
_cell_angle_alpha                84.618(14)
_cell_angle_beta                 97.698(16)
_cell_angle_gamma                102.879(14)
_cell_formula_units_Z            2
_cell_length_a                   6.9800(14)
_cell_length_b                   9.1573(15)
_cell_length_c                   10.849(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      17.2
_cell_measurement_theta_min      12.7
_cell_volume                     668.4(2)
_computing_cell_refinement
;
MSC/AFC Diffractometer Control Software
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
1999)
;
_computing_data_reduction
;
TeXsan for Windows (Molecular Structure Corporation, 1999)
;
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  PLATON
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC 7R'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3477
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.87
_diffrn_standards_decay_%        0.83
_diffrn_standards_interval_time  150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale brown'
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.297
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.826
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.826
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1P)²+2.7752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                2678
_reflns_number_total             3067
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            ta1503.cif
_cod_data_source_block           II
_cod_database_code               2015094
_cod_database_fobs_code          2015094
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
_atom_site_type_symbol
S5 0.24133(6) -0.07178(5) 0.17261(4) 0.02200(10) Uani 1.000 S
O2 0.2200(2) 0.53368(17) 0.30520(17) 0.0382(5) Uani 1.000 O
O51 0.0443(2) -0.16497(16) 0.18292(15) 0.0332(4) Uani 1.000 O
O52 0.3917(2) -0.12624(16) 0.25917(15) 0.0338(4) Uani 1.000 O
O53 0.2911(2) -0.05407(17) 0.04508(14) 0.0345(5) Uani 1.000 O
O71 0.7443(2) 0.38757(18) 0.38199(16) 0.0382(5) Uani 1.000 O
O72 0.5953(2) 0.58001(17) 0.36193(16) 0.0389(5) Uani 1.000 O
C1 0.4086(3) 0.3451(2) 0.29678(17) 0.0214(5) Uani 1.000 C
C2 0.2298(3) 0.3953(2) 0.27685(18) 0.0244(5) Uani 1.000 C
C3 0.0565(3) 0.3015(2) 0.2271(2) 0.0288(6) Uani 1.000 C
C4 0.0594(3) 0.1595(2) 0.19590(19) 0.0269(5) Uani 1.000 C
C5 0.2359(3) 0.1086(2) 0.21482(17) 0.0220(5) Uani 1.000 C
C6 0.4085(3) 0.2011(2) 0.26493(17) 0.0228(5) Uani 1.000 C
C7 0.5962(3) 0.4427(2) 0.35162(18) 0.0256(5) Uani 1.000 C
N1A 0.0053(3) 0.29317(19) 0.56513(18) 0.0282(5) Uani 1.000 N
C1A 0.0033(3) 0.1417(2) 0.53136(17) 0.0232(5) Uani 1.000 C
C2A 0.1793(3) 0.0934(2) 0.54190(19) 0.0263(5) Uani 1.000 C
C3A 0.1758(3) -0.0505(2) 0.51007(19) 0.0272(5) Uani 1.000 C
N1B 0.3612(3) 0.21705(19) -0.10300(18) 0.0269(5) Uani 1.000 N
C1B 0.4327(3) 0.3632(2) -0.04953(17) 0.0230(5) Uani 1.000 C
C2B 0.3014(3) 0.4556(2) -0.0464(2) 0.0289(6) Uani 1.000 C
C3B 0.3700(3) 0.5945(2) 0.0037(2) 0.0296(6) Uani 1.000 C
H2 0.343(6) 0.578(4) 0.331(4) 0.080(12) Uiso 1.000 H
H3 -0.064500 0.335800 0.213300 0.0340 Uiso 1.000 H
H4 -0.059900 0.095800 0.162100 0.0310 Uiso 1.000 H
H6 0.528700 0.166000 0.278300 0.0270 Uiso 1.000 H
H2A 0.301300 0.157800 0.570100 0.0300 Uiso 1.000 H
H3A 0.301100 -0.081600 0.518300 0.0210 Uiso 1.000 H
H11A 0.143(5) 0.349(4) 0.583(3) 0.062(9) Uiso 1.000 H
H12A -0.072(4) 0.340(3) 0.507(3) 0.041(7) Uiso 1.000 H
H13A -0.041(5) 0.287(3) 0.639(3) 0.051(8) Uiso 1.000 H
H2B 0.165400 0.424400 -0.077900 0.0340 Uiso 1.000 H
H3B 0.288200 0.662200 0.017400 0.0210 Uiso 1.000 H
H11B 0.370(5) 0.136(4) -0.041(3) 0.054(8) Uiso 1.000 H
H12B 0.425(5) 0.201(4) -0.165(3) 0.063(10) Uiso 1.000 H
H13B 0.240(4) 0.203(3) -0.130(3) 0.041(7) Uiso 1.000 H
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
O51 S5 O52 . . 111.82(9) no
O51 S5 O53 . . 112.17(9) no
O51 S5 C5 . . 106.72(9) no
O52 S5 O53 . . 111.75(9) no
O52 S5 C5 . . 107.23(9) no
O53 S5 C5 . . 106.75(9) no
C2 O2 H2 . . 105(2) no
H12A N1A H13A . . 109(3) no
H11A N1A H12A . . 115(3) no
C1A N1A H12A . . 111.1(18) no
C1A N1A H13A . . 109.0(17) no
C1A N1A H11A . . 110(2) no
H11A N1A H13A . . 103(3) no
H11B N1B H13B . . 104(3) no
C1B N1B H11B . . 111(2) no
H12B N1B H13B . . 107(3) no
C1B N1B H12B . . 115(2) no
C1B N1B H13B . . 111.7(19) no
H11B N1B H12B . . 106(3) no
C2 C1 C7 . . 121.28(16) no
C2 C1 C6 . . 118.74(18) no
C6 C1 C7 . . 119.98(19) no
C1 C2 C3 . . 120.17(17) no
O2 C2 C1 . . 121.69(18) no
O2 C2 C3 . . 118.14(18) no
C2 C3 C4 . . 120.25(19) no
C3 C4 C5 . . 120.12(19) no
S5 C5 C4 . . 120.31(15) no
S5 C5 C6 . . 119.80(16) no
C4 C5 C6 . . 119.87(17) no
C1 C6 C5 . . 120.84(19) no
O72 C7 C1 . . 117.39(18) no
O71 C7 O72 . . 123.64(19) no
O71 C7 C1 . . 118.95(17) no
C2 C3 H3 . . 120.10 no
C4 C3 H3 . . 119.64 no
C5 C4 H4 . . 120.09 no
C3 C4 H4 . . 119.79 no
C1 C6 H6 . . 119.36 no
C5 C6 H6 . . 119.80 no
N1A C1A C2A . . 119.39(18) no
N1A C1A C3A . 2_556 118.80(19) no
C2A C1A C3A . 2_556 121.82(17) no
C1A C2A C3A . . 118.96(19) no
C1A C3A C2A 2_556 . 119.22(19) no
C3A C2A H2A . . 120.31 no
C1A C2A H2A . . 120.73 no
C2A C3A H3A . . 117.33 no
C1A C3A H3A 2_556 . 123.45 no
N1B C1B C2B . . 119.32(19) no
N1B C1B C3B . 2_665 119.07(18) no
C2B C1B C3B . 2_665 121.62(17) no
C1B C2B C3B . . 119.15(19) no
C1B C3B C2B 2_665 . 119.23(19) no
C1B C2B H2B . . 120.57 no
C3B C2B H2B . . 120.28 no
C2B C3B H3B . . 125.22 no
C1B C3B H3B 2_665 . 115.25 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S5 O51 . . 1.4602(15) no
S5 O52 . . 1.4538(16) no
S5 O53 . . 1.4570(16) no
S5 C5 . . 1.7646(19) no
O2 C2 . . 1.350(2) no
O71 C7 . . 1.242(3) no
O72 C7 . . 1.274(2) no
O2 H2 . . 0.88(4) no
N1A C1A . . 1.464(3) no
N1A H13A . . 0.90(3) no
N1A H12A . . 0.91(3) no
N1A H11A . . 0.99(4) no
N1B C1B . . 1.465(3) no
N1B H12B . . 0.89(3) no
N1B H11B . . 0.96(3) no
N1B H13B . . 0.84(3) no
C1 C2 . . 1.407(3) no
C1 C7 . . 1.496(3) no
C1 C6 . . 1.394(3) no
C2 C3 . . 1.393(3) no
C3 C4 . . 1.379(3) no
C4 C5 . . 1.396(3) no
C5 C6 . . 1.386(3) no
C3 H3 . . 0.9539 no
C4 H4 . . 0.9539 no
C6 H6 . . 0.9524 no
C1A C3A . 2_556 1.384(3) no
C1A C2A . . 1.383(3) no
C2A C3A . . 1.387(3) no
C2A H2A . . 0.9522 no
C3A H3A . . 0.9692 no
C1B C2B . . 1.384(3) no
C1B C3B . 2_665 1.382(3) no
C2B C3B . . 1.390(3) no
C2B H2B . . 0.9540 no
C3B H3B . . 0.9645 no
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 O72 . 0.88(4) 1.74(4) 2.558(2) 152(4) yes
N1A H11A O71 2_666 0.99(4) 2.41(4) 3.114(2) 128(3) yes
N1A H11A O72 2_666 0.99(4) 1.84(4) 2.808(3) 168(3) yes
N1B H11B O53 . 0.96(3) 1.90(3) 2.812(2) 157(3) yes
N1A H12A O71 1_455 0.91(3) 1.83(3) 2.725(3) 166(3) yes
N1B H12B O52 2_655 0.89(3) 2.01(4) 2.868(3) 161(3) yes
N1A H13A O2 2_566 0.90(3) 2.43(3) 3.015(3) 123(2) yes
N1A H13A O51 2_556 0.90(3) 2.14(3) 2.905(3) 143(3) yes
N1B H13B O51 2_555 0.84(3) 1.95(3) 2.794(3) 177(3) yes
C2A H2A O72 2_666 0.95 2.50 3.249(2) 136 no
C3 H3 O71 1_455 0.95 2.54 3.192(3) 126 no
C4 H4 O53 2_555 0.95 2.59 3.385(3) 141 no
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O51 S5 C5 C4 . . . -28.54(18) no
O51 S5 C5 C6 . . . 152.61(15) no
O52 S5 C5 C4 . . . -148.51(16) no
O52 S5 C5 C6 . . . 32.64(18) no
O53 S5 C5 C4 . . . 91.59(17) no
O53 S5 C5 C6 . . . -87.26(17) no
C6 C1 C2 O2 . . . -179.73(18) no
C6 C1 C2 C3 . . . 0.5(3) no
C2 C1 C6 C5 . . . -0.1(3) no
C7 C1 C6 C5 . . . 179.55(17) no
C7 C1 C2 C3 . . . -179.18(18) no
C6 C1 C7 O72 . . . 169.88(18) no
C2 C1 C7 O71 . . . 171.06(19) no
C7 C1 C2 O2 . . . 0.6(3) no
C2 C1 C7 O72 . . . -10.4(3) no
C6 C1 C7 O71 . . . -8.6(3) no
C1 C2 C3 C4 . . . -0.7(3) no
O2 C2 C3 C4 . . . 179.57(18) no
C2 C3 C4 C5 . . . 0.4(3) no
C3 C4 C5 C6 . . . -0.1(3) no
C3 C4 C5 S5 . . . -178.92(16) no
S5 C5 C6 C1 . . . 178.78(14) no
C4 C5 C6 C1 . . . -0.1(3) no
C3A C1A C2A C3A 2_556 . . 0.0(3) no
N1A C1A C2A C3A . . . 179.79(19) no
C2A C1A C3A C2A . 2_556 2_556 0.0(3) no
N1A C1A C3A C2A . 2_556 2_556 -179.79(18) no
C1A C2A C3A C1A . . 2_556 0.0(3) no
N1B C1B C2B C3B . . . -179.62(19) no
C2B C1B C3B C2B . 2_665 2_665 -0.2(3) no
C3B C1B C2B C3B 2_665 . . 0.2(3) no
N1B C1B C3B C2B . 2_665 2_665 179.62(18) no
C1B C2B C3B C1B . . 2_665 -0.2(3) no
