2-(Pyrimidin-2-ylsulfan-yl)acetic acid.

The mol-ecule of the title compound, C(6)H(6)N(2)O(2)S, lies on a crystallographic mirror plane with the methyl-ene H atoms related by mirror symmetry. In the crystal packing, mol-ecules are linked into layers by inter-molecular O-H⋯N and C-H⋯O hydrogen bonds.

Related literature

For the coordination chemistry of thio­ether ligands, see: Li & Bu (2008 ▶); Bu et al. (2003 ▶); Chen et al. (2003 ▶); Demadis & Coucouvanis (1995 ▶); Peng et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H6N2O2S

M = 170.19

Orthorhombic,

a = 14.660 (6) Å

b = 6.579 (2) Å

c = 7.664 (3) Å

V = 739.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.38 mm−1

T = 153 K

0.22 × 0.20 × 0.07 mm

Data collection

Bruker P4 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.920, T max = 0.974

5392 measured reflections

911 independent reflections

828 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.086

S = 1.07

911 reflections

70 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1994 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006400/rz2292sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006400/rz2292Isup2.hkl

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

C6H6N2O2S	F(000) = 352
Mr = 170.19	Dx = 1.529 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 2019 reflections
a = 14.660 (6) Å	θ = 4.3–27.5°
b = 6.579 (2) Å	µ = 0.38 mm−1
c = 7.664 (3) Å	T = 153 K
V = 739.2 (5) Å3	Prism, colorless
Z = 4	0.22 × 0.20 × 0.07 mm

Bruker P4 diffractometer	911 independent reflections
Radiation source: fine-focus sealed tube	828 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 4.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.920, Tmax = 0.974	k = −8→7
5392 measured reflections	l = −9→9

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) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.2357P] where P = (Fo2 + 2Fc2)/3
911 reflections	(Δ/σ)max < 0.001
70 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.36018 (3)	0.2500	0.16539 (6)	0.0429 (2)
O2	0.09853 (9)	0.2500	0.24621 (18)	0.0421 (4)
H1	0.067 (2)	0.2500	0.345 (4)	0.088 (10)*
O1	0.21943 (9)	0.2500	0.42130 (18)	0.0516 (4)
N2	0.50091 (10)	0.2500	−0.0392 (2)	0.0373 (4)
C2	0.24089 (12)	0.2500	0.1111 (3)	0.0415 (5)
H2A	0.2262	0.3696	0.0426	0.050*	0.50
H2B	0.2262	0.1304	0.0426	0.050*	0.50
C3	0.40934 (12)	0.2500	−0.0428 (2)	0.0334 (4)
C4	0.54355 (13)	0.2500	−0.1933 (3)	0.0408 (5)
H4	0.6070	0.2500	−0.1960	0.049*
C1	0.18678 (12)	0.2500	0.2774 (2)	0.0349 (4)
N1	0.35745 (10)	0.2500	−0.1845 (2)	0.0395 (4)
C6	0.40261 (14)	0.2500	−0.3361 (2)	0.0437 (5)
H6	0.3690	0.2500	−0.4390	0.052*
C5	0.49614 (14)	0.2500	−0.3477 (3)	0.0446 (5)
H5	0.5259	0.2500	−0.4549	0.054*

	U11	U22	U33	U12	U13	U23
S1	0.0244 (3)	0.0774 (4)	0.0270 (3)	0.000	−0.00018 (16)	0.000
O2	0.0221 (6)	0.0738 (10)	0.0304 (7)	0.000	−0.0008 (5)	0.000
O1	0.0293 (7)	0.0959 (12)	0.0298 (7)	0.000	−0.0031 (5)	0.000
N2	0.0246 (7)	0.0571 (10)	0.0304 (8)	0.000	0.0002 (6)	0.000
C2	0.0251 (8)	0.0698 (14)	0.0298 (9)	0.000	−0.0004 (7)	0.000
C3	0.0262 (8)	0.0448 (10)	0.0292 (8)	0.000	−0.0004 (7)	0.000
C4	0.0284 (9)	0.0549 (12)	0.0391 (10)	0.000	0.0054 (7)	0.000
C1	0.0254 (8)	0.0481 (11)	0.0311 (9)	0.000	−0.0012 (7)	0.000
N1	0.0293 (8)	0.0593 (11)	0.0299 (8)	0.000	−0.0015 (6)	0.000
C6	0.0403 (11)	0.0632 (13)	0.0277 (9)	0.000	−0.0041 (8)	0.000
C5	0.0416 (10)	0.0624 (14)	0.0299 (9)	0.000	0.0075 (8)	0.000

S1—C3	1.7507 (19)	C2—H2B	0.9700
S1—C2	1.7976 (19)	C3—N1	1.326 (2)
O2—C1	1.316 (2)	C4—C5	1.372 (3)
O2—H1	0.89 (3)	C4—H4	0.9300
O1—C1	1.202 (2)	N1—C6	1.337 (2)
N2—C4	1.336 (2)	C6—C5	1.374 (3)
N2—C3	1.343 (2)	C6—H6	0.9300
C2—C1	1.501 (3)	C5—H5	0.9300
C2—H2A	0.9700
C3—S1—C2	100.92 (9)	N2—C4—H4	119.2
C1—O2—H1	111 (2)	C5—C4—H4	119.2
C4—N2—C3	116.72 (16)	O1—C1—O2	123.91 (17)
C1—C2—S1	108.51 (13)	O1—C1—C2	124.65 (16)
C1—C2—H2A	110.0	O2—C1—C2	111.44 (16)
S1—C2—H2A	110.0	C3—N1—C6	115.33 (17)
C1—C2—H2B	110.0	N1—C6—C5	123.38 (18)
S1—C2—H2B	110.0	N1—C6—H6	118.3
H2A—C2—H2B	108.4	C5—C6—H6	118.3
N1—C3—N2	126.17 (17)	C4—C5—C6	116.72 (18)
N1—C3—S1	120.70 (14)	C4—C5—H5	121.6
N2—C3—S1	113.13 (13)	C6—C5—H5	121.6
N2—C4—C5	121.68 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···N2i	0.89 (3)	1.78 (3)	2.663 (2)	178 (3)
C6—H6···O1ii	0.93	2.44	3.266 (3)	148
C5—H5···O2iii	0.93	2.47	3.403 (3)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯N2i	0.89 (3)	1.78 (3)	2.663 (2)	178 (3)
C6—H6⋯O1ii	0.93	2.44	3.266 (3)	148
C5—H5⋯O2iii	0.93	2.47	3.403 (3)	178

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