2-(Carboxy-methyl-sulfan-yl)pyridine-3-carboxylic acid monohydrate.

The title compound, C(8)H(7)NO(4)S·H(2)O, was obtained by reaction of 2-mercaptopyridine-3-carboxylic acid with chloro-acetic acid. In the mol-ecular structure, the dihedral angle between the two least-squares planes defined by the pyridine ring and the carb-oxy group is 8.32 (9)°. The carboxy-methyl-sulfanyl group makes a torsion angle of 82.64 (12)° with the pyridine ring. An intra-molecular O-H⋯N hydrogen bond between the acidic function of the carboxy-methyl-sulfanyl group and the pyridine N atom stabilizes the conformation, whereas inter-molecular O-H⋯O hydrogen bonding with the uncoordinated water mol-ecules is responsible for packing of the structure, leading to chains propagating in [001].

Related literature

For derivatives of 2-mercaptopyridine-3-carboxylic acid and compounds with 2-mercaptopyridine-3-carboxyl­ate ligands, see: Panagiotis et al. (2003 ▶); Smith & Sagatys (2003 ▶); Humphrey et al. (2006 ▶); Ma et al. (2004 ▶); Quintal et al. (2002 ▶).

Experimental

Crystal data

C8H7NO4S·H2O

M = 231.22

Triclinic,

a = 7.2824 (2) Å

b = 7.3132 (2) Å

c = 10.9090 (4) Å

α = 77.901 (2)°

β = 71.787 (2)°

γ = 62.590 (2)°

V = 488.43 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.48 × 0.43 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.853, T max = 0.987

7375 measured reflections

2217 independent reflections

1910 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.090

S = 1.02

2217 reflections

148 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Crystal Impact, 2008 ▶); software used to prepare mat­erial for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016120/wm2333sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016120/wm2333Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H7NO4S·H2O	Z = 2
Mr = 231.22	F(000) = 240
Triclinic, P1	Dx = 1.572 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2824 (2) Å	Cell parameters from 3676 reflections
b = 7.3132 (2) Å	θ = 2.0–27.6°
c = 10.9090 (4) Å	µ = 0.33 mm−1
α = 77.901 (2)°	T = 296 K
β = 71.787 (2)°	Sheet, colourless
γ = 62.590 (2)°	0.48 × 0.43 × 0.04 mm
V = 488.43 (3) Å3

Bruker APEXII CCD diffractometer	2217 independent reflections
Radiation source: fine-focus sealed tube	1910 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.853, Tmax = 0.987	k = −9→9
7375 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.088P] where P = (Fo2 + 2Fc2)/3
2217 reflections	(Δ/σ)max = 0.001
148 parameters	Δρmax = 0.24 e Å−3
5 restraints	Δρmin = −0.24 e Å−3

Geometry. 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.

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.

	x	y	z	Uiso*/Ueq
S1	−0.82738 (6)	0.36814 (5)	1.36087 (3)	0.04015 (13)
N1	−0.5286 (2)	0.09443 (18)	1.19465 (11)	0.0391 (3)
O2	−0.92675 (19)	0.12020 (17)	1.57117 (11)	0.0515 (3)
O4	−0.6871 (2)	0.41454 (18)	1.04260 (11)	0.0545 (3)
C5	−0.6485 (2)	0.1157 (2)	1.31717 (13)	0.0336 (3)
O1	−0.7165 (2)	−0.20956 (19)	1.61482 (11)	0.0523 (3)
C4	−0.6261 (2)	−0.0580 (2)	1.40665 (13)	0.0344 (3)
O3	−0.8462 (2)	0.74565 (18)	1.07003 (11)	0.0612 (4)
C6	−0.7717 (2)	−0.0376 (2)	1.53873 (14)	0.0381 (3)
C3	−0.3782 (3)	−0.0926 (2)	1.15876 (15)	0.0446 (4)
H3A	−0.2974	−0.1047	1.0734	0.054*
C8	−0.7529 (2)	0.5679 (2)	1.11102 (15)	0.0431 (3)
C7	−0.7046 (3)	0.5195 (2)	1.24178 (14)	0.0408 (3)
H7A	−0.7496	0.6490	1.2771	0.049*
H7B	−0.5511	0.4459	1.2295	0.049*
C2	−0.4654 (2)	−0.2483 (2)	1.36726 (15)	0.0412 (3)
H2A	−0.4430	−0.3646	1.4256	0.049*
C1	−0.3389 (3)	−0.2664 (2)	1.24242 (16)	0.0461 (4)
H1A	−0.2298	−0.3931	1.2158	0.055*
O1W	−0.0210 (2)	0.1439 (2)	1.15804 (12)	0.0589 (3)
H1WA	0.034 (3)	0.020 (2)	1.145 (2)	0.071*
H1WB	−0.081 (3)	0.200 (3)	1.0980 (19)	0.071*
H4	−0.626 (3)	0.302 (3)	1.087 (2)	0.071*
H1	−0.809 (3)	−0.177 (3)	1.6845 (18)	0.071*

	U11	U22	U33	U12	U13	U23
S1	0.0438 (2)	0.0341 (2)	0.0296 (2)	−0.00903 (16)	−0.00324 (15)	−0.00379 (14)
N1	0.0419 (7)	0.0382 (6)	0.0309 (6)	−0.0151 (5)	−0.0021 (5)	−0.0057 (5)
O2	0.0511 (7)	0.0457 (6)	0.0380 (6)	−0.0125 (5)	0.0027 (5)	−0.0045 (5)
O4	0.0775 (9)	0.0477 (7)	0.0319 (6)	−0.0222 (6)	−0.0154 (6)	0.0017 (5)
C5	0.0334 (7)	0.0354 (7)	0.0301 (7)	−0.0134 (6)	−0.0065 (5)	−0.0043 (5)
O1	0.0528 (7)	0.0501 (6)	0.0378 (6)	−0.0165 (6)	−0.0070 (5)	0.0093 (5)
C4	0.0351 (7)	0.0357 (7)	0.0326 (7)	−0.0158 (6)	−0.0080 (6)	−0.0020 (5)
O3	0.0693 (8)	0.0445 (7)	0.0426 (6)	−0.0061 (6)	−0.0137 (6)	0.0073 (5)
C6	0.0417 (8)	0.0420 (8)	0.0328 (7)	−0.0206 (7)	−0.0102 (6)	0.0008 (6)
C3	0.0426 (8)	0.0450 (8)	0.0376 (8)	−0.0160 (7)	0.0029 (6)	−0.0121 (6)
C8	0.0408 (8)	0.0432 (8)	0.0352 (8)	−0.0148 (7)	−0.0052 (6)	0.0031 (6)
C7	0.0482 (9)	0.0333 (7)	0.0376 (7)	−0.0147 (6)	−0.0123 (7)	−0.0001 (6)
C2	0.0428 (8)	0.0345 (7)	0.0437 (8)	−0.0154 (6)	−0.0103 (7)	−0.0011 (6)
C1	0.0414 (8)	0.0369 (8)	0.0504 (9)	−0.0107 (6)	−0.0025 (7)	−0.0124 (7)
O1W	0.0736 (9)	0.0588 (8)	0.0365 (6)	−0.0272 (7)	−0.0108 (6)	0.0050 (6)

S1—C5	1.7606 (14)	O3—C8	1.2184 (18)
S1—C7	1.8151 (15)	C3—C1	1.368 (2)
N1—C3	1.3421 (19)	C3—H3A	0.9300
N1—C5	1.3438 (18)	C8—C7	1.507 (2)
O2—C6	1.2057 (18)	C7—H7A	0.9700
O4—C8	1.2949 (19)	C7—H7B	0.9700
O4—H4	0.861 (15)	C2—C1	1.379 (2)
C5—C4	1.4078 (19)	C2—H2A	0.9300
O1—C6	1.3180 (18)	C1—H1A	0.9300
O1—H1	0.834 (16)	O1W—H1WA	0.831 (15)
C4—C2	1.388 (2)	O1W—H1WB	0.830 (15)
C4—C6	1.487 (2)
C5—S1—C7	101.30 (7)	O3—C8—O4	121.27 (15)
C3—N1—C5	119.77 (13)	O3—C8—C7	121.00 (15)
C8—O4—H4	108.4 (15)	O4—C8—C7	117.70 (13)
N1—C5—C4	120.67 (13)	C8—C7—S1	116.34 (11)
N1—C5—S1	117.29 (10)	C8—C7—H7A	108.2
C4—C5—S1	122.02 (11)	S1—C7—H7A	108.2
C6—O1—H1	103.5 (16)	C8—C7—H7B	108.2
C2—C4—C5	117.92 (13)	S1—C7—H7B	108.2
C2—C4—C6	121.27 (13)	H7A—C7—H7B	107.4
C5—C4—C6	120.81 (13)	C1—C2—C4	120.56 (14)
O2—C6—O1	123.86 (14)	C1—C2—H2A	119.7
O2—C6—C4	122.82 (13)	C4—C2—H2A	119.7
O1—C6—C4	113.31 (13)	C3—C1—C2	118.13 (14)
N1—C3—C1	122.77 (14)	C3—C1—H1A	120.9
N1—C3—H3A	118.6	C2—C1—H1A	120.9
C1—C3—H3A	118.6	H1WA—O1W—H1WB	101.9 (18)
C3—N1—C5—C4	−3.5 (2)	C2—C4—C6—O1	7.13 (19)
C3—N1—C5—S1	174.95 (11)	C5—C4—C6—O1	−173.44 (13)
C7—S1—C5—N1	−23.50 (12)	C5—N1—C3—C1	−0.4 (2)
C7—S1—C5—C4	154.90 (12)	O3—C8—C7—S1	117.68 (15)
N1—C5—C4—C2	5.0 (2)	O4—C8—C7—S1	−64.05 (18)
S1—C5—C4—C2	−173.31 (11)	C5—S1—C7—C8	82.64 (12)
N1—C5—C4—C6	−174.42 (12)	C5—C4—C2—C1	−2.8 (2)
S1—C5—C4—C6	7.24 (18)	C6—C4—C2—C1	176.64 (13)
C2—C4—C6—O2	−171.59 (14)	N1—C3—C1—C2	2.6 (2)
C5—C4—C6—O2	7.8 (2)	C4—C2—C1—C3	−0.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3i	0.83 (2)	2.02 (2)	2.8319 (18)	166 (2)
O1W—H1WB···O3ii	0.83 (2)	1.98 (2)	2.7784 (18)	162 (2)
O1—H1···O1Wiii	0.83 (2)	1.76 (2)	2.5917 (17)	171 (2)
O4—H4···N1	0.86 (2)	1.72 (2)	2.5778 (17)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O3i	0.83 (2)	2.02 (2)	2.8319 (18)	166 (2)
O1W—H1WB⋯O3ii	0.83 (2)	1.98 (2)	2.7784 (18)	162 (2)
O1—H1⋯O1Wiii	0.83 (2)	1.76 (2)	2.5917 (17)	171 (2)
O4—H4⋯N1	0.86 (2)	1.72 (2)	2.5778 (17)	172 (2)

Symmetry codes: (i) ; (ii) ; (iii) .