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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 6| June 2010| Page o1298
https://doi.org/10.1107/S1600536810016120

2-(Carb­oxy­methyl­sulfan­yl)pyridine-3-carboxylic acid monohydrate

Xiao-Juan Wanga and Yun-Long Fenga*

aZhejiang Key Laboratory for Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, Zhejiang 321004, People's Republic of China
*Correspondence e-mail: sky37@zjnu.edu.cn

(Received 23 April 2010; accepted 2 May 2010; online 8 May 2010)

The title compound, C8H7NO4S·H2O, was obtained by reaction of 2-mercaptopyridine-3-carboxylic acid with chloro­acetic acid. In the mol­ecular structure, the dihedral angle between the two least-squares planes defined by the pyridine ring and the carb­oxy group is 8.32 (9)°. The carboxy­methyl­sulfanyl group makes a torsion angle of 82.64 (12)° with the pyridine ring. An intra­molecular O—H⋯N hydrogen bond between the acidic function of the carboxy­methyl­sulfanyl group and the pyridine N atom stabilizes the conformation, whereas inter­molecular O—H⋯O hydrogen bonding with the uncoordinated water mol­ecules 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[Panagiotis, C. Z., Sotiris, K. H., Nick, H., Adonis, M., Stavroula, S., Yang, M. & Yu, X. L. (2003). Inorg. Chim. Acta, 343, 361-365.]); Smith & Sagatys (2003[Smith, G. & Sagatys, D. S. (2003). Acta Cryst. E59, o540-o541.]); Humphrey et al. (2006[Humphrey, S. M., Alberola, A., Gómez Garcíab, C. J. & Wood, P. T. (2006). Chem. Commun. pp. 1607-1609.]); Ma et al. (2004[Ma, C., Jiang, Q. & Zhang, R. F. (2004). Can. J. Chem. 82, 608-615.]); Quintal et al. (2002[Quintal, S. M. O., Nogueira, H. I. S., Félixa, V. & Drew, M. G. B. (2002). J. Chem. Soc. Dalton Trans. pp. 4479-4487.]).

[Scheme 1]

Experimental

Crystal data

  • C8H7NO4S·H2O

  • Mr = 231.22

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.853, Tmax = 0.987

  • 7375 measured reflections

  • 2217 independent reflections

  • 1910 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 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

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) x+1, y-1, z; (ii) -x-1, -y+1, -z+2; (iii) -x-1, -y, -z+3.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Crystal Impact, 2008[Crystal Impact (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare mat­erial for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016120/wm2333Isup2.hkl

checkCIF report


Comment top

2-Mercaptopyridine-3-carboxylic acid is an interesting ligand because of its potential versatile coordinate behavior. It may act as a deprotonated ligand through either the carboxylate or the thiolate group, such as 2-mercaptopyridine-3-carboxylate hydrate (Smith et al., 2003) or 2-mercapto-nicotinic acid (Panagiotis et al., 2003). Thus it can act as a monodentate (O or N), bidentate (O, O or O, N) or chelating (O, O or O, N) ligand interacting with metal ions, and a variety of coordination polymers have been characterised (Humphrey et al., 2006; Ma et al., 2004; Quintal et al., 2002). In this work, we report a new derivative, 2-(carboxymethylsulfanyl)pyridine-3-carboxylic acid, (I), which was obtained by reaction of 2-mercaptopyridine-3-carboxylic acid with chloroacetic acid.

The molecular structure of (I) is presented in Fig. 1. The carboxylate group is almost parallel to the pyridine group with a dihedral angle of 8.32 (9)°, while the carboxymethylsulfanyl group makes a torsion angle of 82.64 (12)° with the pyridine ring. The carboxylic O atoms, pyridine N atom together with lattice water molecules are involved in hydrogen-bonding interactions (Fig. 2). In detail, the structure is stabilized by an intramolecular O—H···N hydrogen bond between the carboxy function of the carboxymethylsulfanyl group and the pyridine N atom. The other carboxy function acts as a donor and acceptor group for intermolecular O—H···O hydrogen bonds with the adjacent lattice water molecules which results in the formation of a chain structure running along the c direction.

Related literature top

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

Experimental top

The mixture of 2-mercaptopyridine-3-carboxylic acid (1.552 g, 10.0 mmol) and chloroacetic acid (2.835 g, 30.0 mmol) was stirred and refluxed under basic condition in which sodium hydroxide solution was needed to keep the pH around 11. After reaction for 4 h at 328 K, the mixture was cooled to room temperature. By adjusting the pH around 3 with concentrated hydrochloric acid, a white precipitate appeared rapidly. The solid was filtered off and washed with water. Single crystals suitable for X-ray diffraction were obtained in the mother liquid after evaporation within a few days.

Refinement top

The carbon-bound H-atoms were positioned geometrically and included in the refinement using a riding model [C—H 0.93, 0.97 Å Uiso(H) = 1.2Ueq(C)]. The oxygen-bound H-atoms were located in a difference Fourier maps and refined with an O—H distance restraint of 0.83 Å [Uiso(H) = 1.2Ueq(O)].

Structure description top

2-Mercaptopyridine-3-carboxylic acid is an interesting ligand because of its potential versatile coordinate behavior. It may act as a deprotonated ligand through either the carboxylate or the thiolate group, such as 2-mercaptopyridine-3-carboxylate hydrate (Smith et al., 2003) or 2-mercapto-nicotinic acid (Panagiotis et al., 2003). Thus it can act as a monodentate (O or N), bidentate (O, O or O, N) or chelating (O, O or O, N) ligand interacting with metal ions, and a variety of coordination polymers have been characterised (Humphrey et al., 2006; Ma et al., 2004; Quintal et al., 2002). In this work, we report a new derivative, 2-(carboxymethylsulfanyl)pyridine-3-carboxylic acid, (I), which was obtained by reaction of 2-mercaptopyridine-3-carboxylic acid with chloroacetic acid.

The molecular structure of (I) is presented in Fig. 1. The carboxylate group is almost parallel to the pyridine group with a dihedral angle of 8.32 (9)°, while the carboxymethylsulfanyl group makes a torsion angle of 82.64 (12)° with the pyridine ring. The carboxylic O atoms, pyridine N atom together with lattice water molecules are involved in hydrogen-bonding interactions (Fig. 2). In detail, the structure is stabilized by an intramolecular O—H···N hydrogen bond between the carboxy function of the carboxymethylsulfanyl group and the pyridine N atom. The other carboxy function acts as a donor and acceptor group for intermolecular O—H···O hydrogen bonds with the adjacent lattice water molecules which results in the formation of a chain structure running along the c direction.

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

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the one-dimensional chain structure of (I). Intermolecular hydrogen bonds interactions are depicted by dashed lines.
2-(Carboxymethylsulfanyl)pyridine-3-carboxylic acid monohydrate top
Crystal data top
C8H7NO4S·H2OZ = 2
Mr = 231.22F(000) = 240
Triclinic, P1Dx = 1.572 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2824 (2) ÅCell parameters from 3676 reflections
b = 7.3132 (2) Åθ = 2.0–27.6°
c = 10.9090 (4) ŵ = 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
Data collection top
Bruker APEXII CCD
diffractometer		2217 independent reflections
Radiation source: fine-focus sealed tube1910 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.6°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.853, Tmax = 0.987k = −9→9
7375 measured reflectionsl = −14→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H 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 parametersΔρmax = 0.24 e Å−3
5 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C8H7NO4S·H2Oγ = 62.590 (2)°
Mr = 231.22V = 488.43 (3) Å3
Triclinic, P1Z = 2
a = 7.2824 (2) ÅMo Kα radiation
b = 7.3132 (2) ŵ = 0.33 mm−1
c = 10.9090 (4) ÅT = 296 K
α = 77.901 (2)°0.48 × 0.43 × 0.04 mm
β = 71.787 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		2217 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1910 reflections with I > 2σ(I)
Tmin = 0.853, Tmax = 0.987Rint = 0.024
7375 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0325 restraints
wR(F2) = 0.090H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.24 e Å−3
2217 reflectionsΔρmin = −0.24 e Å−3
148 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/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−0.2974−0.10471.07340.054*
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−0.74960.64901.27710.049*
H7B−0.55110.44591.22950.049*
C2−0.4654 (2)−0.2483 (2)1.36726 (15)0.0412 (3)
H2A−0.4430−0.36461.42560.049*
C1−0.3389 (3)−0.2664 (2)1.24242 (16)0.0461 (4)
H1A−0.2298−0.39311.21580.055*
O1W−0.0210 (2)0.1439 (2)1.15804 (12)0.0589 (3)
H1WA0.034 (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*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0438 (2)0.0341 (2)0.0296 (2)−0.00903 (16)−0.00324 (15)−0.00379 (14)
N10.0419 (7)0.0382 (6)0.0309 (6)−0.0151 (5)−0.0021 (5)−0.0057 (5)
O20.0511 (7)0.0457 (6)0.0380 (6)−0.0125 (5)0.0027 (5)−0.0045 (5)
O40.0775 (9)0.0477 (7)0.0319 (6)−0.0222 (6)−0.0154 (6)0.0017 (5)
C50.0334 (7)0.0354 (7)0.0301 (7)−0.0134 (6)−0.0065 (5)−0.0043 (5)
O10.0528 (7)0.0501 (6)0.0378 (6)−0.0165 (6)−0.0070 (5)0.0093 (5)
C40.0351 (7)0.0357 (7)0.0326 (7)−0.0158 (6)−0.0080 (6)−0.0020 (5)
O30.0693 (8)0.0445 (7)0.0426 (6)−0.0061 (6)−0.0137 (6)0.0073 (5)
C60.0417 (8)0.0420 (8)0.0328 (7)−0.0206 (7)−0.0102 (6)0.0008 (6)
C30.0426 (8)0.0450 (8)0.0376 (8)−0.0160 (7)0.0029 (6)−0.0121 (6)
C80.0408 (8)0.0432 (8)0.0352 (8)−0.0148 (7)−0.0052 (6)0.0031 (6)
C70.0482 (9)0.0333 (7)0.0376 (7)−0.0147 (6)−0.0123 (7)−0.0001 (6)
C20.0428 (8)0.0345 (7)0.0437 (8)−0.0154 (6)−0.0103 (7)−0.0011 (6)
C10.0414 (8)0.0369 (8)0.0504 (9)−0.0107 (6)−0.0025 (7)−0.0124 (7)
O1W0.0736 (9)0.0588 (8)0.0365 (6)−0.0272 (7)−0.0108 (6)0.0050 (6)
Geometric parameters (Å, º) top
S1—C51.7606 (14)O3—C81.2184 (18)
S1—C71.8151 (15)C3—C11.368 (2)
N1—C31.3421 (19)C3—H3A0.9300
N1—C51.3438 (18)C8—C71.507 (2)
O2—C61.2057 (18)C7—H7A0.9700
O4—C81.2949 (19)C7—H7B0.9700
O4—H40.861 (15)C2—C11.379 (2)
C5—C41.4078 (19)C2—H2A0.9300
O1—C61.3180 (18)C1—H1A0.9300
O1—H10.834 (16)O1W—H1WA0.831 (15)
C4—C21.388 (2)O1W—H1WB0.830 (15)
C4—C61.487 (2)
C5—S1—C7101.30 (7)O3—C8—O4121.27 (15)
C3—N1—C5119.77 (13)O3—C8—C7121.00 (15)
C8—O4—H4108.4 (15)O4—C8—C7117.70 (13)
N1—C5—C4120.67 (13)C8—C7—S1116.34 (11)
N1—C5—S1117.29 (10)C8—C7—H7A108.2
C4—C5—S1122.02 (11)S1—C7—H7A108.2
C6—O1—H1103.5 (16)C8—C7—H7B108.2
C2—C4—C5117.92 (13)S1—C7—H7B108.2
C2—C4—C6121.27 (13)H7A—C7—H7B107.4
C5—C4—C6120.81 (13)C1—C2—C4120.56 (14)
O2—C6—O1123.86 (14)C1—C2—H2A119.7
O2—C6—C4122.82 (13)C4—C2—H2A119.7
O1—C6—C4113.31 (13)C3—C1—C2118.13 (14)
N1—C3—C1122.77 (14)C3—C1—H1A120.9
N1—C3—H3A118.6C2—C1—H1A120.9
C1—C3—H3A118.6H1WA—O1W—H1WB101.9 (18)
C3—N1—C5—C4−3.5 (2)C2—C4—C6—O17.13 (19)
C3—N1—C5—S1174.95 (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—C4154.90 (12)O3—C8—C7—S1117.68 (15)
N1—C5—C4—C25.0 (2)O4—C8—C7—S1−64.05 (18)
S1—C5—C4—C2−173.31 (11)C5—S1—C7—C882.64 (12)
N1—C5—C4—C6−174.42 (12)C5—C4—C2—C1−2.8 (2)
S1—C5—C4—C67.24 (18)C6—C4—C2—C1176.64 (13)
C2—C4—C6—O2−171.59 (14)N1—C3—C1—C22.6 (2)
C5—C4—C6—O27.8 (2)C4—C2—C1—C3−0.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O3i0.83 (2)2.02 (2)2.8319 (18)166 (2)
O1W—H1WB···O3ii0.83 (2)1.98 (2)2.7784 (18)162 (2)
O1—H1···O1Wiii0.83 (2)1.76 (2)2.5917 (17)171 (2)
O4—H4···N10.86 (2)1.72 (2)2.5778 (17)172 (2)
Symmetry codes: (i) x+1, y−1, z; (ii) −x−1, −y+1, −z+2; (iii) −x−1, −y, −z+3.

Experimental details

Crystal data
Chemical formulaC8H7NO4S·H2O
Mr231.22
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)7.2824 (2), 7.3132 (2), 10.9090 (4)
α, β, γ (°)77.901 (2), 71.787 (2), 62.590 (2)
V (Å3)488.43 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.33
Crystal size (mm)0.48 × 0.43 × 0.04
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.853, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections		7375, 2217, 1910
Rint0.024
(sin θ/λ)max (Å−1)0.653
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.090, 1.02
No. of reflections2217
No. of parameters148
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.24, −0.24

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Crystal Impact, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O3i0.831 (15)2.018 (16)2.8319 (18)166 (2)
O1W—H1WB···O3ii0.830 (15)1.976 (17)2.7784 (18)162 (2)
O1—H1···O1Wiii0.834 (16)1.764 (16)2.5917 (17)171 (2)
O4—H4···N10.861 (15)1.722 (16)2.5778 (17)172 (2)
Symmetry codes: (i) x+1, y−1, z; (ii) −x−1, −y+1, −z+2; (iii) −x−1, −y, −z+3.
 

References

First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCrystal Impact (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationHumphrey, S. M., Alberola, A., Gómez Garcíab, C. J. & Wood, P. T. (2006). Chem. Commun. pp. 1607–1609.  Web of Science CSD CrossRef Google Scholar
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ISSN: 2056-9890
Volume 66| Part 6| June 2010| Page o1298
https://doi.org/10.1107/S1600536810016120
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