2-{[4-(Pyridin-2-yl)pyrimidin-2-yl]sulfan-yl}acetic acid.

In the title mol-ecule, C(11)H(9)N(3)O(2)S, the pyridine and pyrimidine rings are almost parallel [dihedral angle = 6.7 (1)°]. In the crystal, adjacent mol-ecules are joined by O-H⋯N and C-H⋯O hydrogen bonds, leading to the formation of a sheet parallel to (10[Formula: see text]).

Related literature

For details of the synthesis and general background, see: Dong et al. (2009 ▶); Wang (2011 ▶). For the crystal structures of coord­ination complexes with related ligands, see: Du et al. (2004 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C11H9N3O2S

M = 247.28

Monoclinic,

a = 6.5722 (2) Å

b = 22.4650 (8) Å

c = 7.4314 (2) Å

β = 93.237 (2)°

V = 1095.45 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 291 K

0.28 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.920, T max = 0.950

10868 measured reflections

2524 independent reflections

2116 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.05

2524 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811039791/kj2186sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811039791/kj2186Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811039791/kj2186Isup3.cml

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

C11H9N3O2S	F(000) = 512.0
Mr = 247.28	Dx = 1.499 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2524 reflections
a = 6.5722 (2) Å	θ = 1.8–27.5°
b = 22.4650 (8) Å	µ = 0.29 mm−1
c = 7.4314 (2) Å	T = 291 K
β = 93.237 (2)°	Block, pale yellow
V = 1095.45 (6) Å3	0.28 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2524 independent reflections
Radiation source: fine-focus sealed tube	2116 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.920, Tmax = 0.950	k = −24→29
10868 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0449P)2 + 0.289P] where P = (Fo2 + 2Fc2)/3
2524 reflections	(Δ/σ)max = 0.001
155 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses.

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
C1	−0.0901 (2)	0.34978 (6)	0.26132 (19)	0.0342 (3)
C2	−0.3668 (2)	0.39680 (7)	0.1300 (2)	0.0412 (4)
H2A	−0.4973	0.3959	0.0747	0.049*
C3	−0.2718 (2)	0.45062 (7)	0.1562 (2)	0.0391 (3)
H3	−0.3370	0.4860	0.1229	0.047*
C4	−0.0745 (2)	0.45042 (6)	0.23433 (19)	0.0327 (3)
C5	0.0431 (2)	0.50633 (6)	0.25998 (19)	0.0333 (3)
C6	0.2462 (2)	0.50591 (7)	0.3208 (2)	0.0427 (4)
H6	0.3120	0.4702	0.3493	0.051*
C7	0.3493 (3)	0.55934 (8)	0.3385 (2)	0.0511 (4)
H7	0.4862	0.5602	0.3778	0.061*
C8	0.2464 (3)	0.61115 (7)	0.2972 (2)	0.0493 (4)
H8	0.3113	0.6478	0.3096	0.059*
C9	0.0444 (3)	0.60757 (7)	0.2367 (3)	0.0490 (4)
H9	−0.0242	0.6428	0.2078	0.059*
C10	0.2527 (2)	0.30146 (7)	0.4321 (2)	0.0380 (3)
H10A	0.3269	0.3242	0.3463	0.046*
H10B	0.2369	0.3259	0.5380	0.046*
C11	0.3674 (2)	0.24555 (7)	0.4832 (2)	0.0365 (3)
N1	0.01710 (17)	0.39939 (5)	0.28821 (16)	0.0340 (3)
N2	−0.27844 (18)	0.34541 (6)	0.18112 (18)	0.0391 (3)
N3	−0.0580 (2)	0.55666 (6)	0.21748 (19)	0.0432 (3)
O1	0.30963 (19)	0.19622 (5)	0.4458 (2)	0.0623 (4)
O2	0.53762 (17)	0.25707 (5)	0.57657 (19)	0.0544 (3)
H2	0.5945	0.2257	0.6057	0.082*
S1	0.00702 (6)	0.280700 (17)	0.33349 (6)	0.04496 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0331 (7)	0.0315 (7)	0.0371 (8)	−0.0008 (6)	−0.0044 (6)	0.0020 (6)
C2	0.0329 (7)	0.0395 (8)	0.0500 (9)	0.0000 (6)	−0.0100 (6)	0.0044 (7)
C3	0.0357 (7)	0.0329 (8)	0.0477 (9)	0.0046 (6)	−0.0053 (6)	0.0035 (6)
C4	0.0344 (7)	0.0297 (7)	0.0338 (7)	0.0004 (5)	0.0004 (6)	0.0001 (5)
C5	0.0373 (7)	0.0279 (7)	0.0345 (7)	0.0011 (6)	−0.0004 (6)	−0.0005 (6)
C6	0.0425 (8)	0.0330 (8)	0.0512 (9)	−0.0010 (6)	−0.0106 (7)	0.0027 (7)
C7	0.0470 (9)	0.0454 (10)	0.0591 (11)	−0.0091 (7)	−0.0137 (8)	−0.0012 (8)
C8	0.0612 (10)	0.0321 (8)	0.0543 (10)	−0.0104 (7)	0.0000 (8)	−0.0057 (7)
C9	0.0564 (10)	0.0281 (8)	0.0628 (11)	0.0042 (7)	0.0045 (8)	−0.0008 (7)
C10	0.0340 (7)	0.0297 (8)	0.0491 (9)	0.0002 (6)	−0.0078 (6)	0.0004 (6)
C11	0.0324 (7)	0.0313 (8)	0.0452 (8)	0.0003 (6)	−0.0041 (6)	−0.0005 (6)
N1	0.0328 (6)	0.0284 (6)	0.0399 (7)	−0.0004 (5)	−0.0052 (5)	0.0024 (5)
N2	0.0347 (6)	0.0331 (7)	0.0482 (7)	−0.0028 (5)	−0.0096 (5)	0.0040 (5)
N3	0.0418 (7)	0.0286 (7)	0.0587 (8)	0.0041 (5)	0.0000 (6)	0.0007 (6)
O1	0.0526 (7)	0.0291 (6)	0.1011 (11)	−0.0001 (5)	−0.0329 (7)	−0.0024 (6)
O2	0.0424 (6)	0.0322 (6)	0.0852 (9)	0.0028 (5)	−0.0269 (6)	−0.0038 (6)
S1	0.0384 (2)	0.0272 (2)	0.0670 (3)	−0.00354 (15)	−0.01691 (18)	0.00762 (17)

C1—N1	1.3276 (18)	C7—C8	1.372 (2)
C1—N2	1.3466 (18)	C7—H7	0.9300
C1—S1	1.7507 (15)	C8—C9	1.380 (2)
C2—N2	1.3377 (19)	C8—H8	0.9300
C2—C3	1.369 (2)	C9—N3	1.331 (2)
C2—H2A	0.9300	C9—H9	0.9300
C3—C4	1.3909 (19)	C10—C11	1.503 (2)
C3—H3	0.9300	C10—S1	1.7964 (14)
C4—N1	1.3453 (17)	C10—H10A	0.9700
C4—C5	1.4815 (19)	C10—H10B	0.9700
C5—N3	1.3401 (18)	C11—O1	1.1991 (18)
C5—C6	1.385 (2)	C11—O2	1.3085 (17)
C6—C7	1.381 (2)	O2—H2	0.8200
C6—H6	0.9300
N1—C1—N2	126.48 (13)	C7—C8—C9	118.45 (15)
N1—C1—S1	121.11 (10)	C7—C8—H8	120.8
N2—C1—S1	112.41 (10)	C9—C8—H8	120.8
N2—C2—C3	122.31 (13)	N3—C9—C8	123.84 (15)
N2—C2—H2A	118.8	N3—C9—H9	118.1
C3—C2—H2A	118.8	C8—C9—H9	118.1
C2—C3—C4	117.60 (13)	C11—C10—S1	108.22 (10)
C2—C3—H3	121.2	C11—C10—H10A	110.1
C4—C3—H3	121.2	S1—C10—H10A	110.1
N1—C4—C3	121.20 (13)	C11—C10—H10B	110.1
N1—C4—C5	117.57 (12)	S1—C10—H10B	110.1
C3—C4—C5	121.23 (13)	H10A—C10—H10B	108.4
N3—C5—C6	122.60 (14)	O1—C11—O2	123.76 (14)
N3—C5—C4	115.89 (12)	O1—C11—C10	124.47 (13)
C6—C5—C4	121.49 (13)	O2—C11—C10	111.76 (12)
C7—C6—C5	118.94 (15)	C1—N1—C4	116.48 (12)
C7—C6—H6	120.5	C2—N2—C1	115.86 (12)
C5—C6—H6	120.5	C9—N3—C5	117.29 (14)
C8—C7—C6	118.87 (15)	C11—O2—H2	109.5
C8—C7—H7	120.6	C1—S1—C10	101.46 (7)
C6—C7—H7	120.6

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2i	0.82	1.87	2.694 (2)	178
C2—H2A···O1ii	0.93	2.58	3.230 (2)	127
C8—H8···O2iii	0.93	2.48	3.392 (2)	165
C9—H9···O1iv	0.93	2.45	3.296 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2i	0.82	1.87	2.694 (2)	178
C2—H2A⋯O1ii	0.93	2.58	3.230 (2)	127
C8—H8⋯O2iii	0.93	2.48	3.392 (2)	165
C9—H9⋯O1iv	0.93	2.45	3.296 (2)	151

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