4-(4-Carb­oxy-1,3-thia­zol-2-yl)pyridinium 3-carb­oxy-4-hydroxy­benzene­sulfonate dihydrate

Du, Z.-X.; Li, J.-X.

doi:10.1107/S1600536808030924

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o2044

doi:10.1107/S1600536808030924

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4-(4-Carboxy-1,3-thiazol-2-yl)pyridinium 3-carboxy-4-hydroxybenzenesulfonate dihydrate

Zhong-Xiang Du ^a ^* and Jun-Xia Li ^a

^aDepartment of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, Henan 471022, People's Republic of China
^*Correspondence e-mail: dzx6281@126.com

(Received 1 September 2008; accepted 25 September 2008; online 30 September 2008)

In the crystal structure of the title compound, C₉H₇N₂O₂S⁺·C₇H₅O₆S⁻·2H₂O, an H atom from the 5-sulfosalicylic acid is transferred to the pyridyl N atom, forming a salt. The dihedral angle between the thiazole and pyridinium rings is 5.909 (5)°. The crystal packing is determined by O—H⋯O and N—H⋯O hydrogen bonds involving water molecules.

Related literature

For related structures, see: Chen et al. (2007 ); Ellsworth et al. (2006 ); Su et al. (2004 ).

Experimental

Crystal data

C₉H₇N₂O₂S⁺·C₇H₅O₆S⁻·2H₂O
M_r = 460.43
Triclinic, $[P \overline 1]$
a = 8.6234 (14) Å
b = 10.6065 (17) Å
c = 10.7979 (17) Å
α = 97.799 (2)°
β = 94.479 (2)°
γ = 99.885 (2)°
V = 958.7 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 291 (2) K
0.44 × 0.29 × 0.24 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.867, T_max = 0.924
7016 measured reflections
3494 independent reflections
3095 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.092
S = 1.03
3494 reflections
275 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.88	2.599 (2)	146
O3—H3⋯O9	0.82	1.71	2.5269 (17)	171
O8—H8⋯O4ⁱ	0.82	1.89	2.6979 (18)	171
O9—H1W⋯O6ⁱⁱ	0.84	1.93	2.753 (2)	165
O9—H2W⋯O5ⁱⁱⁱ	0.83	1.89	2.713 (2)	172
O10—H3W⋯O2	0.81	2.32	2.9001 (19)	129
O10—H4W⋯O7^iv	0.81	2.27	2.835 (2)	128
N2—H2D⋯O10^v	0.86	1.86	2.689 (2)	162
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y+1, z; (iii) -x, -y+1, -z+1; (iv) x, y+1, z+1; (v) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808030924/kp2193sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030924/kp2193Isup2.hkl

checkCIF report

Comment top

2-(4-Pyridyl)thiazole-4-carboxylic acid (HPTCA), which is an asymmetric, chelating ligand, has been studied in recent years. Five of its transition metal complexes (Chen et al., 2007; Ellsworth et al., 2006; Su et al., 2004) were reported. In this paper we describe its salt with 5-sulfosalicylic acid (H₃SSA), (I).

The crystal structure of the title molecule comprises 2-(4-pyridylomium)thiazole-4-carboxylic acid, a 5-sulfosalicylic acid anion and two water molecules (Fig.1). The H atom of the 5-sulfosalicylic acid is transferred to the pyridyl N-atom of 2-(4-pyridyl)thiazole-4-carboxylic acid, thus forming a salt. The dihedral angle between the thiazole and pyridinium rings is 5.909 (5)°. The N—H and O—H groups are involved in intra- and intermolecular hydrogen bonds with water molecules generating the 3-dimensional hydrogen bond network (Table 1 and Fig. 2).

Related literature top

For related literature, see: Chen et al. (2007); Ellsworth et al. (2006); Su et al. (2004).

Experimental top

The ligand HPTCA (1 mmol, 0.21 g) and H₃SSA.2H₂O (1 mmol, 0.25 g) were dissolved in solvent mixture of water and methanol (20 mL, v/v 1:1). To this solution, Cu(CH₃COO)₂.4H₂O (1 mmol, 0.26 g) was added and the resulting mixture was stirred and refluxed at 353 K for 3 h, then cooled to room temperature. After filtration and evaporation in air for five days, colourless claviform-shaped crystals were obtained in a yield of 43%. Analysis, found (%): C, 41.75; H, 3.51; N, 6.02; S,13.87. C₁₆H₁₆N₂O₁₀S₂ requires (%): C,41.70; H,3.47; N,6.08; S,13.90. (The elemental analysis indicates that the copper(II) is not coordinated by the ligands) (CCDC number 685021)

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal packing of (I), showing hydrogen bonds as dashed lines. For the sake of clarity, H atoms on C atoms have been omitted.

4-(4-Carboxy-1,3-thiazol-2-yl)pyridinium 3-carboxy-4-hydroxybenzenesulfonate dihydrate top

Crystal data top

C₉H₇N₂O₂S⁺·C₇H₅O₆S⁻·2H₂O	Z = 2
M_r = 460.43	F(000) = 476
Triclinic, P1	D_x = 1.595 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6234 (14) Å	Cell parameters from 4068 reflections
b = 10.6065 (17) Å	θ = 2.4–28.1°
c = 10.7979 (17) Å	µ = 0.34 mm⁻¹
α = 97.799 (2)°	T = 291 K
β = 94.479 (2)°	Claviform, colourless
γ = 99.885 (2)°	0.44 × 0.29 × 0.24 mm
V = 958.7 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3494 independent reflections
Radiation source: fine-focus sealed tube	3095 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.867, T_max = 0.924	k = −12→12
7016 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0504P)² + 0.314P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3494 reflections	Δρ_max = 0.31 e Å⁻³
275 parameters	Δρ_min = −0.29 e Å⁻³
6 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (2)

Crystal data top

C₉H₇N₂O₂S⁺·C₇H₅O₆S⁻·2H₂O	γ = 99.885 (2)°
M_r = 460.43	V = 958.7 (3) Å³
Triclinic, P1	Z = 2
a = 8.6234 (14) Å	Mo Kα radiation
b = 10.6065 (17) Å	µ = 0.34 mm⁻¹
c = 10.7979 (17) Å	T = 291 K
α = 97.799 (2)°	0.44 × 0.29 × 0.24 mm
β = 94.479 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3494 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3095 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.924	R_int = 0.014
7016 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	6 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.03	Δρ_max = 0.31 e Å⁻³
3494 reflections	Δρ_min = −0.29 e Å⁻³
275 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell e.s.d.'s are taken

into account individually in the estimation of e.s.d.'s in distances, angles

and torsion angles; correlations between e.s.d.'s in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F², conventional R-factors R are based

on F, with F set to zero for negative F². The threshold expression of

F² > σ(F²) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F² are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.25056 (5)	0.11285 (4)	0.35763 (4)	0.03667 (14)
S2	1.01768 (5)	0.41512 (5)	0.19381 (4)	0.04482 (15)
O1	0.52983 (18)	0.53943 (14)	0.76634 (12)	0.0532 (4)
H1	0.4963	0.6058	0.7574	0.080*
O2	0.34176 (16)	0.67695 (12)	0.67191 (12)	0.0472 (3)
O3	0.18259 (15)	0.59188 (11)	0.49653 (12)	0.0432 (3)
H3	0.1683	0.6667	0.4998	0.065*
O4	0.30140 (18)	0.15439 (12)	0.24126 (12)	0.0513 (4)
O5	0.07938 (16)	0.09571 (14)	0.35499 (15)	0.0595 (4)
O6	0.31219 (19)	0.00026 (13)	0.38592 (14)	0.0577 (4)
O7	0.61923 (18)	0.12933 (14)	−0.10879 (16)	0.0643 (4)
O8	0.81979 (18)	0.03591 (13)	−0.04892 (13)	0.0525 (4)
H8	0.7748	−0.0241	−0.1027	0.079*
O9	0.11825 (18)	0.81397 (13)	0.48548 (15)	0.0566 (4)
H1W	0.1851	0.8757	0.4688	0.085*
H2W	0.0648	0.8431	0.5397	0.085*
O10	0.35251 (19)	0.94663 (14)	0.77184 (18)	0.0746 (5)
H3W	0.3066	0.8901	0.7160	0.112*
H4W	0.4477	0.9618	0.7742	0.112*
N1	0.77420 (17)	0.36608 (13)	0.03035 (13)	0.0356 (3)
N2	0.7588 (2)	0.83610 (15)	0.15551 (16)	0.0488 (4)
H2D	0.7349	0.9120	0.1660	0.059*
C1	0.33096 (19)	0.24035 (15)	0.48162 (15)	0.0324 (4)
C2	0.4457 (2)	0.22332 (18)	0.57360 (17)	0.0398 (4)
H2	0.4793	0.1444	0.5709	0.048*
C3	0.5089 (2)	0.32448 (19)	0.66860 (17)	0.0428 (4)
H3A	0.5849	0.3130	0.7300	0.051*
C4	0.4600 (2)	0.44306 (17)	0.67308 (15)	0.0368 (4)
C5	0.34238 (19)	0.46005 (15)	0.58262 (14)	0.0310 (3)
C6	0.27899 (19)	0.35698 (15)	0.48679 (15)	0.0312 (3)
H6	0.2013	0.3672	0.4261	0.037*
C7	0.28871 (19)	0.58539 (16)	0.58768 (15)	0.0336 (4)
C8	0.7104 (2)	0.62363 (17)	0.04650 (16)	0.0396 (4)
H8A	0.6538	0.5612	−0.0173	0.048*
C9	0.6759 (2)	0.74537 (19)	0.06439 (18)	0.0473 (5)
H9	0.5946	0.7655	0.0132	0.057*
C10	0.8772 (3)	0.81171 (18)	0.23019 (19)	0.0517 (5)
H10	0.9334	0.8769	0.2917	0.062*
C11	0.9166 (2)	0.69063 (18)	0.21681 (18)	0.0456 (4)
H11	0.9993	0.6738	0.2688	0.055*
C12	0.8314 (2)	0.59344 (16)	0.12459 (15)	0.0342 (4)
C13	0.8626 (2)	0.46044 (16)	0.10910 (15)	0.0336 (4)
C14	0.8288 (2)	0.25269 (16)	0.03559 (15)	0.0354 (4)
C15	0.9591 (2)	0.26100 (18)	0.11859 (17)	0.0420 (4)
H15	1.0088	0.1921	0.1320	0.050*
C16	0.7430 (2)	0.13402 (17)	−0.04781 (17)	0.0402 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0437 (3)	0.0231 (2)	0.0418 (3)	0.00772 (17)	0.00411 (18)	−0.00162 (17)
S2	0.0427 (3)	0.0475 (3)	0.0405 (3)	0.0097 (2)	−0.01003 (19)	0.0000 (2)
O1	0.0644 (9)	0.0472 (8)	0.0389 (7)	0.0037 (7)	−0.0181 (6)	−0.0035 (6)
O2	0.0590 (8)	0.0326 (7)	0.0432 (7)	0.0049 (6)	−0.0022 (6)	−0.0095 (6)
O3	0.0501 (7)	0.0283 (6)	0.0480 (7)	0.0111 (5)	−0.0082 (6)	−0.0028 (5)
O4	0.0753 (10)	0.0361 (7)	0.0368 (7)	0.0011 (6)	0.0047 (6)	−0.0024 (5)
O5	0.0440 (8)	0.0457 (8)	0.0774 (10)	0.0017 (6)	0.0034 (7)	−0.0207 (7)
O6	0.0805 (10)	0.0317 (7)	0.0647 (9)	0.0235 (7)	0.0058 (8)	0.0046 (6)
O7	0.0581 (9)	0.0427 (8)	0.0821 (11)	0.0191 (7)	−0.0240 (8)	−0.0207 (7)
O8	0.0696 (9)	0.0377 (7)	0.0499 (8)	0.0260 (7)	−0.0084 (7)	−0.0067 (6)
O9	0.0660 (9)	0.0342 (7)	0.0736 (10)	0.0169 (6)	0.0145 (7)	0.0081 (7)
O10	0.0556 (9)	0.0383 (8)	0.1174 (14)	0.0034 (7)	0.0108 (9)	−0.0263 (8)
N1	0.0414 (8)	0.0307 (7)	0.0332 (7)	0.0090 (6)	−0.0031 (6)	0.0001 (6)
N2	0.0659 (11)	0.0289 (8)	0.0519 (10)	0.0092 (7)	0.0134 (8)	0.0022 (7)
C1	0.0370 (9)	0.0281 (8)	0.0322 (8)	0.0062 (7)	0.0051 (7)	0.0034 (7)
C2	0.0419 (10)	0.0378 (9)	0.0430 (10)	0.0134 (8)	0.0039 (8)	0.0106 (8)
C3	0.0404 (10)	0.0505 (11)	0.0380 (9)	0.0094 (8)	−0.0043 (7)	0.0126 (8)
C4	0.0390 (9)	0.0404 (9)	0.0278 (8)	0.0010 (7)	0.0002 (7)	0.0039 (7)
C5	0.0338 (8)	0.0298 (8)	0.0281 (8)	0.0026 (7)	0.0052 (6)	0.0028 (6)
C6	0.0342 (8)	0.0295 (8)	0.0285 (8)	0.0053 (6)	−0.0008 (6)	0.0027 (6)
C7	0.0359 (8)	0.0297 (8)	0.0321 (8)	0.0002 (7)	0.0055 (7)	0.0003 (7)
C8	0.0465 (10)	0.0344 (9)	0.0352 (9)	0.0076 (8)	−0.0003 (7)	−0.0023 (7)
C9	0.0567 (12)	0.0403 (10)	0.0457 (11)	0.0141 (9)	0.0041 (9)	0.0033 (8)
C10	0.0633 (13)	0.0330 (10)	0.0494 (11)	−0.0050 (9)	0.0027 (10)	−0.0075 (8)
C11	0.0500 (11)	0.0388 (10)	0.0412 (10)	0.0005 (8)	−0.0061 (8)	−0.0026 (8)
C12	0.0398 (9)	0.0319 (9)	0.0286 (8)	0.0022 (7)	0.0049 (7)	0.0009 (7)
C13	0.0374 (9)	0.0341 (9)	0.0277 (8)	0.0054 (7)	0.0006 (7)	0.0024 (7)
C14	0.0416 (9)	0.0334 (9)	0.0325 (8)	0.0118 (7)	0.0026 (7)	0.0036 (7)
C15	0.0448 (10)	0.0421 (10)	0.0411 (10)	0.0171 (8)	0.0002 (8)	0.0043 (8)
C16	0.0475 (10)	0.0329 (9)	0.0407 (10)	0.0147 (8)	0.0007 (8)	−0.0001 (7)

Geometric parameters (Å, º) top

S1—O6	1.4469 (14)	C1—C6	1.382 (2)
S1—O5	1.4535 (14)	C1—C2	1.398 (2)
S1—O4	1.4613 (14)	C2—C3	1.383 (3)
S1—C1	1.7731 (17)	C2—H2	0.9300
S2—C15	1.6968 (19)	C3—C4	1.390 (3)
S2—C13	1.7334 (17)	C3—H3A	0.9300
O1—C4	1.355 (2)	C4—C5	1.404 (2)
O1—H1	0.8200	C5—C6	1.401 (2)
O2—C7	1.234 (2)	C5—C7	1.476 (2)
O3—C7	1.308 (2)	C6—H6	0.9300
O3—H3	0.8200	C8—C9	1.366 (3)
O7—C16	1.199 (2)	C8—C12	1.397 (2)
O8—C16	1.325 (2)	C8—H8A	0.9300
O8—H8	0.8200	C9—H9	0.9300
O9—H1W	0.8436	C10—C11	1.376 (3)
O9—H2W	0.8319	C10—H10	0.9300
O10—H3W	0.8145	C11—C12	1.393 (2)
O10—H4W	0.8065	C11—H11	0.9300
N1—C13	1.308 (2)	C12—C13	1.471 (2)
N1—C14	1.371 (2)	C14—C15	1.365 (2)
N2—C10	1.333 (3)	C14—C16	1.487 (2)
N2—C9	1.342 (3)	C15—H15	0.9300
N2—H2D	0.8600

O6—S1—O5	113.03 (9)	C1—C6—H6	119.7
O6—S1—O4	112.45 (9)	C5—C6—H6	119.7
O5—S1—O4	110.37 (9)	O2—C7—O3	122.98 (16)
O6—S1—C1	106.53 (8)	O2—C7—C5	121.86 (16)
O5—S1—C1	106.90 (8)	O3—C7—C5	115.17 (14)
O4—S1—C1	107.15 (8)	C9—C8—C12	119.66 (17)
C15—S2—C13	89.46 (8)	C9—C8—H8A	120.2
C4—O1—H1	109.5	C12—C8—H8A	120.2
C7—O3—H3	109.5	N2—C9—C8	120.27 (18)
C16—O8—H8	109.5	N2—C9—H9	119.9
H1W—O9—H2W	108.7	C8—C9—H9	119.9
H3W—O10—H4W	115.9	N2—C10—C11	120.40 (17)
C13—N1—C14	110.35 (14)	N2—C10—H10	119.8
C10—N2—C9	121.80 (17)	C11—C10—H10	119.8
C10—N2—H2D	119.1	C10—C11—C12	119.39 (18)
C9—N2—H2D	119.1	C10—C11—H11	120.3
C6—C1—C2	120.15 (15)	C12—C11—H11	120.3
C6—C1—S1	119.39 (12)	C11—C12—C8	118.45 (16)
C2—C1—S1	120.46 (13)	C11—C12—C13	122.13 (16)
C3—C2—C1	119.70 (16)	C8—C12—C13	119.41 (15)
C3—C2—H2	120.2	N1—C13—C12	122.45 (15)
C1—C2—H2	120.2	N1—C13—S2	114.42 (13)
C2—C3—C4	120.60 (16)	C12—C13—S2	123.13 (12)
C2—C3—H3A	119.7	N1—C14—C15	115.53 (16)
C4—C3—H3A	119.7	N1—C14—C16	118.19 (14)
O1—C4—C3	117.74 (15)	C15—C14—C16	126.27 (16)
O1—C4—C5	122.23 (16)	C14—C15—S2	110.25 (13)
C3—C4—C5	120.04 (16)	C14—C15—H15	124.9
C4—C5—C6	118.92 (15)	S2—C15—H15	124.9
C4—C5—C7	120.28 (15)	O7—C16—O8	124.15 (17)
C6—C5—C7	120.79 (15)	O7—C16—C14	123.19 (16)
C1—C6—C5	120.57 (15)	O8—C16—C14	112.65 (15)

O6—S1—C1—C6	−173.04 (13)	C12—C8—C9—N2	0.8 (3)
O5—S1—C1—C6	−51.93 (16)	C9—N2—C10—C11	−0.9 (3)
O4—S1—C1—C6	66.39 (15)	N2—C10—C11—C12	−0.1 (3)
O6—S1—C1—C2	6.85 (17)	C10—C11—C12—C8	1.5 (3)
O5—S1—C1—C2	127.96 (15)	C10—C11—C12—C13	−177.15 (17)
O4—S1—C1—C2	−113.72 (15)	C9—C8—C12—C11	−1.8 (3)
C6—C1—C2—C3	−1.1 (3)	C9—C8—C12—C13	176.87 (16)
S1—C1—C2—C3	179.01 (13)	C14—N1—C13—C12	−179.49 (15)
C1—C2—C3—C4	−0.3 (3)	C14—N1—C13—S2	0.04 (18)
C2—C3—C4—O1	−178.07 (16)	C11—C12—C13—N1	173.78 (16)
C2—C3—C4—C5	1.7 (3)	C8—C12—C13—N1	−4.8 (2)
O1—C4—C5—C6	178.11 (15)	C11—C12—C13—S2	−5.7 (2)
C3—C4—C5—C6	−1.6 (2)	C8—C12—C13—S2	175.67 (13)
O1—C4—C5—C7	−0.9 (3)	C15—S2—C13—N1	−0.04 (14)
C3—C4—C5—C7	179.36 (15)	C15—S2—C13—C12	179.49 (15)
C2—C1—C6—C5	1.1 (2)	C13—N1—C14—C15	0.0 (2)
S1—C1—C6—C5	−178.97 (12)	C13—N1—C14—C16	−179.94 (15)
C4—C5—C6—C1	0.2 (2)	N1—C14—C15—S2	0.0 (2)
C7—C5—C6—C1	179.24 (14)	C16—C14—C15—S2	179.90 (15)
C4—C5—C7—O2	−1.7 (2)	C13—S2—C15—C14	0.02 (14)
C6—C5—C7—O2	179.26 (15)	N1—C14—C16—O7	−8.5 (3)
C4—C5—C7—O3	177.84 (15)	C15—C14—C16—O7	171.6 (2)
C6—C5—C7—O3	−1.2 (2)	N1—C14—C16—O8	170.21 (15)
C10—N2—C9—C8	0.6 (3)	C15—C14—C16—O8	−9.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.88	2.599 (2)	146
O3—H3···O9	0.82	1.71	2.5269 (17)	171
O8—H8···O4ⁱ	0.82	1.89	2.6979 (18)	171
O9—H1W···O6ⁱⁱ	0.84	1.93	2.753 (2)	165
O9—H2W···O5ⁱⁱⁱ	0.83	1.89	2.713 (2)	172
O10—H3W···O2	0.81	2.32	2.9001 (19)	129
O10—H4W···O7^iv	0.81	2.27	2.835 (2)	128
N2—H2D···O10^v	0.86	1.86	2.689 (2)	162

Symmetry codes: (i) −x+1, −y, −z; (ii) x, y+1, z; (iii) −x, −y+1, −z+1; (iv) x, y+1, z+1; (v) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₉H₇N₂O₂S⁺·C₇H₅O₆S⁻·2H₂O
M_r	460.43
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	8.6234 (14), 10.6065 (17), 10.7979 (17)
α, β, γ (°)	97.799 (2), 94.479 (2), 99.885 (2)
V (Å³)	958.7 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.44 × 0.29 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.867, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	7016, 3494, 3095
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.092, 1.03
No. of reflections	3494
No. of parameters	275
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.29

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.88	2.599 (2)	145.5
O3—H3···O9	0.82	1.71	2.5269 (17)	170.9
O8—H8···O4ⁱ	0.82	1.89	2.6979 (18)	170.8
O9—H1W···O6ⁱⁱ	0.84	1.93	2.753 (2)	164.8
O9—H2W···O5ⁱⁱⁱ	0.83	1.89	2.713 (2)	172.2
O10—H3W···O2	0.81	2.32	2.9001 (19)	128.5
O10—H4W···O7^iv	0.81	2.27	2.835 (2)	127.9
N2—H2D···O10^v	0.86	1.86	2.689 (2)	161.5

Symmetry codes: (i) −x+1, −y, −z; (ii) x, y+1, z; (iii) −x, −y+1, −z+1; (iv) x, y+1, z+1; (v) −x+1, −y+2, −z+1.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20471026) and the Natural Science Foundation of Henan Province (No. 0311021200).

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, X. D., Wu, H. F., Zhao, X. H., Zhao, X. J. & Du, M. (2007). Cryst. Growth Des. 7, 124–131. Web of Science CSD CrossRef Google Scholar
Ellsworth, J. M., Su, C. Y., Khaliq, Z., Hipp, R. E., Goforth, A. M., Smith, M. D. & Loye, H. C. (2006). J. Mol. Struct. 796, 86–94. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Su, C. Y., Smith, M. D., Goforth, A. M. & Loye, H. C. (2004). Inorg. Chem. 43, 6881–6883. Web of Science CSD CrossRef PubMed CAS Google Scholar

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Volume 64| Part 10| October 2008| Page o2044

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