2-(2-Pyridylsulfan-yl)acetic acid.

Abstract

All non-H atoms of the title compound, C(7)H(7)NO(2)S, lie on a crystallographic mirror plane, with the two methyl-ene H atoms bis-ected by this plane. The crystal packing is characterized by inter-molecular C-H⋯O and O-H⋯N contacts, which link the mol-ecules into infinite zigzag chains parallel to [010].

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2-(2-Pyridylsulfanyl)acetic acid
Xiao-Feng Li, Yan An,* Hui-Guo Chen, Li-Hua Dong and
Wei Yan
Institute of Marine Materials Science and Engineering, Shanghai Maritime University,
Shanghai 201306, People’s Republic of China.
Correspondence e-mail: smuchem@yahoo.com.cn
Received 14 December 2009; accepted 16 December 2009
Key indicators: single-crystal X-ray study; T = 293 K; mean ?(C–C) = 0.006 A ˚;
R factor = 0.050; wR factor = 0.140; data-to-parameter ratio = 12.0.
All non-H atoms of the title compound, C7H7NO2S, lie on a
crystallographic mirror plane, with the two methylene H
atoms bisected by this plane. The crystal packing is
characterized by intermolecular C—H???O and O—H???N
contacts, which link the molecules into infinite zigzag chains
parallel to [010].
Related literature
For background to the design of similar ligands, see: Akrivos
(2001); Ye et al. (2005). For bond-length data, see: Allen et al.
(1987).
Experimental
Crystal data
C7H7NO2S
Mr= 169.20
Orthorhombic, Pnma
a = 14.5521 (19) A˚
b = 6.6774 (13) A˚
c = 7.7212 (19) A˚
V = 750.3 (3) A˚3
Z = 4
Mo K? radiation
? = 0.37 mm?1
T = 293 K
0.37 ? 0.35 ? 0.27 mm
Data collection
Bruker APEXII CCD
diffractometer
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
Tmin= 0.875, Tmax= 0.906
1160 measured reflections
805 independent reflections
473 reflections with I > 2?(I)
Rint= 0.066
Refinement
R[F2> 2?(F2)] = 0.050
wR(F2) = 0.140
S = 1.00
805 reflections
67 parameters
H-atom parameters constrained
??max= 0.27 e A˚?3
??min= ?0.35 e A˚?3
Table 1
Hydrogen-bond geometry (A˚,?).
D—H???A
O2—H2B???N1i
C2—H2A???O2ii
C3—H3A???O1iii
Symmetry codes: (i) x ?1
D—HH???AD???AD—H???A
0.82
0.93
0.93
1.79
2.50
2.46
2.606 (5)
3.410 (6)
3.229 (5)
175
167
140
2;y;?z þ1
2; (ii) x þ1
2;y;?z þ3
2; (iii) x;y;z þ 1.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT
(Bruker, 2004); data reduction: SAINT; program(s) used to solve
structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
structure:SHELXL97 (Sheldrick,
SHELXTL (Sheldrick, 2008); software used to prepare material for
publication: SHELXTL.
2008);moleculargraphics:
The authors thank the Project of the Shanghai Municipal
EducationCommission (2008080,
10YZ111, 10ZZ98), the ‘Chen Guang’ project supported by
the Shanghai Municipal Education Commission and the
Shanghai Education Development Foundation (09 C G52),
the Innovative Activities of University Students in Shanghai
Maritime University Project (090503) and the State Key
Laboratory of Pollution Control and Resource Re-use Foun-
dation (PCRRF09001) for financial support.
2008068,09YZ245,
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: SJ2712).
References
Akrivos, P. D. (2001). Coord. Chem. Rev. 213, 181–210.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor,
R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,
USA.
Sheldrick, G. M. (2004). SADABS. University of Go ¨ttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Ye, B. H., Tong, M. L. & Chen, X. M. (2005). Coord. Chem. Rev. 249, 545–565.
organic compounds
o234
Li et al.
doi:10.1107/S1600536809054373
Acta Cryst. (2010). E66, o234
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368

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supplementary materials

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supplementary materials
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Acta Cryst. (2010). E66, o234 [ doi:10.1107/S1600536809054373 ]
2-(2-Pyridylsulfanyl)acetic acid
X.-F. Li, Y. An, H.-G. Chen, L.-H. Dong and W. Yan
Comment
Compounds involving heterocyclic thiolate groups are ambidentate ligands which can form various metal-organic coordina-
tion structures via coordination of the exocyclic sulfur or the endocyclic nitrogen atoms (Akrivos, 2001). Similarly, carboxyl-
ic acids also exhibit diverse coordination modes in different metal complexes (Ye et al., 2005). In attempts to develop novel
coordination frameworks, we have designed and synthesized the title compound, 2-(pyridin-2-ylthio)acetic acid (I), as a
potentially multidentate ligand. Its crystal structure is reported here.
The single-crystal X-ray analysis of I reveals that all the bond lengths in compound I are within normal ranges (Allen
et al., 1987). All the non-hydrogen atoms in each molecule are coplanar with the methylene hydrogen atoms related by
mirror symmetry (Fig. 1). In the crystal structure molecules are linked into infinite, one dimensional, zigzag chains due to
intermolecular H-bonding (Fig. 2, Table 2).
Experimental
The title compound was prepared by heating a mixture of 2-pyridinethione (0.335 g, 3 mmol), chloroacetic acid (0.292 g, 3.1
mmol) and sodium hydroxide (0.248 g, 6.2 mmol) in ethanol at 353 K with magnetic stirring for 8 h. The pH of the solution
was adjusted to 6 with hydrochloric acid. Yellow crystals were obtained after being recrystrallized twice from the ethanol
solution (yield 78%). Analysis, calculated for C7H7NO2S: C 49.69, H 4.17, N 8.28%; Found: C 50.06, H 4.27, N 8.06%.
Refinement
All H-atoms were positioned geometrically and refined using a riding model with d(C-H) = 0.93Å, Uiso=1.2Ueq (C) for
aromatic 0.97Å, Uiso = 1.2Ueq (C) for CH2, and 0.82Å, Uiso = 1.5Ueq (O) for the OH group.
Figures
Fig. 1. View of the structure of I. Displacement ellipsoids are drawn at the 30% probability
level.
Fig. 2. Crystal packin of the title compound viewed down the b axis.

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supplementary materials
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2-(2-Pyridylsulfanyl)acetic acid
Crystal data
C7H7NO2S
F(000) = 352
Dx = 1.498 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 343 reflections
θ = 2.8–28.0°
µ = 0.37 mm−1
T = 293 K
Mr = 169.20
Orthorhombic, Pnma
Hall symbol: -P 2ac 2n
a = 14.5521 (19) Å
b = 6.6774 (13) Å
c = 7.7212 (19) Å
V = 750.3 (3) Å3
Z = 4
Block, yellow
0.37 × 0.35 × 0.27 mm
Data collection
Bruker APEXII CCD
diffractometer
Radiation source: fine-focus sealed tube
graphite
φ and ω scans
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
Tmin = 0.875, Tmax = 0.906
1160 measured reflections
805 independent reflections
473 reflections with I > 2σ(I)
Rint = 0.066
θmax = 26.0°, θmin = 2.8°
h = −17→1
k = −1→8
l = −9→1
Refinement
Refinement on F2
Primary atom site location: structure-invariant direct
methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring
sites
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.050
wR(F2) = 0.140
H-atom parameters constrained
S = 1.00
w = 1/[σ2(Fo2) + (0.0634P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.003
Δρmax = 0.27 e Å−3
Δρmin = −0.35 e Å−3
805 reflections
67 parameters
0 restraints
Special details
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 mat-
rix. 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.

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supplementary materials
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Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, convention-
al 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)
x
0.34558 (7)
0.5342 (3)
0.5981
0.4919 (3)
0.5262
0.3973 (3)
0.3668
0.3481 (3)
0.2842
0.3950 (3)
0.2251 (2)
0.2093
0.2093
0.1723 (3)
0.4877 (2)
0.2095 (2)
0.08419 (18)
0.0569
y
0.2500
0.2500
0.2500
0.2500
0.2500
0.2500
0.2500
0.2500
0.2500
0.2500
0.2500
0.1322
0.3678
0.2500
0.2500
0.2500
0.2500
0.2500
z
0.33858 (14)
0.6916 (6)
0.6879
0.8503 (6)
0.9520
0.8547 (6)
0.9605
0.7029 (5)
0.7050
0.5463 (5)
0.3861 (5)
0.4533
0.4533
0.2160 (6)
0.5405 (5)
0.0775 (4)
0.2437 (4)
0.1508
Uiso*/Ueq
0.0562 (6)
0.0583 (19)
0.070*
0.0560 (17)
0.067*
0.0545 (17)
0.065*
0.0484 (15)
0.058*
0.0452 (15)
0.0459 (15)
0.055*
0.055*
0.0454 (15)
0.0474 (13)
0.0638 (13)
0.0557 (12)
0.084*
Occ. (<1)
S1
C1
H1A
C2
H2A
C3
H3A
C4
H4A
C5
C6
H6A
H6B
C7
N1
O1
O2
H2B
0.50
0.50
Atomic displacement parameters (Å2)
U11
0.0240 (6)
0.025 (2)
0.042 (3)
0.041 (3)
0.028 (2)
0.023 (2)
0.0196 (19)
0.027 (2)
0.0240 (17)
0.0268 (15)
0.0211 (16)
U22
0.1177 (15)
0.109 (6)
0.095 (5)
0.099 (5)
0.086 (5)
0.083 (5)
0.088 (5)
0.080 (5)
0.088 (4)
0.134 (4)
0.112 (4)
U33
0.0269 (6)
0.041 (3)
0.031 (2)
0.023 (2)
0.031 (2)
0.030 (2)
0.030 (2)
0.029 (2)
0.0304 (18)
0.0310 (16)
0.0345 (16)
U12
0.000
0.000
0.000
0.000
0.000
0.000
0.000
0.000
0.000
0.000
0.000
U13
−0.0001 (5)
−0.0074 (19)
−0.007 (2)
0.006 (2)
0.0029 (18)
−0.0021 (17)
−0.0003 (17)
0.0009 (18)
−0.0001 (15)
−0.0006 (13)
−0.0018 (13)
U23
0.000
0.000
0.000
0.000
0.000
0.000
0.000
0.000
0.000
0.000
0.000
S1
C1
C2
C3
C4
C5
C6
C7
N1
O1
O2
Geometric parameters (Å, °)
S1—C5
S1—C6
C1—N1
C1—C2
1.757 (4)
1.791 (4)
1.348 (5)
1.372 (6)
C4—C5
C4—H4A
C5—N1
C6—C7
1.389 (6)
0.9300
1.350 (5)
1.522 (6)