3-{[4-(4-Pyrid-yl)pyrimidin-2-yl]sulfanylmeth-yl}benzoic acid.

The title compound, C(17)H(13)N(3)O(2)S, was prepared by reaction of 4-(4-pyrid-yl)pyrimidine-2-thiol with 3-(bromo-meth-yl)benzoic acid under basic conditions. Each pair of mol-ecules is mutually linked via O-H⋯N hydrogen bonds, forming a dimer. The packing of the dimers is stablized by C-H⋯π inter-actions involving the methyl-ene unit of the -CH(2)S- linkage and benzene rings.

Related literature

For monodentate and chelating ligands, see: Raper (1996 ▶). For the structures of binuclear and polynuclear complexes with bridging heterocyclic thio­nate ligands, see: Raper (1997 ▶). For O—H⋯N inter­actions, see: Han et al. (2008 ▶). For C—H⋯π inter­actions, see: Choi et al. (2008 ▶).

Experimental

Crystal data

C17H13N3O2S

M = 323.36

Triclinic,

a = 4.4130 (9) Å

b = 10.458 (2) Å

c = 16.432 (3) Å

α = 87.79 (3)°

β = 89.90 (3)°

γ = 80.48 (3)°

V = 747.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 298 (2) K

0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.934, T max = 0.977

3108 measured reflections

2724 independent reflections

1685 reflections with I > 2σ(I)

R int = 0.048

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.170

S = 1.04

2724 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036799/si2127sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036799/si2127Isup2.hkl

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

C17H13N3O2S	Z = 2
Mr = 323.36	F000 = 336
Triclinic, P1	Dx = 1.437 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 4.4130 (9) Å	Cell parameters from 25 reflections
b = 10.458 (2) Å	θ = 9–12º
c = 16.432 (3) Å	µ = 0.23 mm−1
α = 87.79 (3)º	T = 298 (2) K
β = 89.90 (3)º	Prism, colorless
γ = 80.48 (3)º	0.30 × 0.10 × 0.10 mm
V = 747.4 (3) Å3

Enraf–Nonius CAD-4 diffractometer	Rint = 0.048
Radiation source: fine-focus sealed tube	θmax = 25.3º
Monochromator: graphite	θmin = 1.2º
T = 298(2) K	h = 0→5
ω/2θ scans	k = −12→12
Absorption correction: ψ scan(North et al., 1968)	l = −19→19
Tmin = 0.934, Tmax = 0.977	3 standard reflections
3108 measured reflections	every 200 reflections
2724 independent reflections	intensity decay: 1%
1685 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071	H-atom parameters constrained
wR(F2) = 0.170	w = 1/[σ2(Fo2) + (0.05P)2 + P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2724 reflections	Δρmax = 0.35 e Å−3
208 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S	0.1838 (3)	0.34695 (12)	0.92472 (7)	0.0633 (4)
O1	0.6060 (10)	0.6024 (3)	0.5857 (2)	0.0916 (13)
O2	0.6987 (9)	0.7953 (3)	0.61531 (19)	0.0795 (11)
H2A	0.7614	0.7948	0.5683	0.119*
N1	1.0847 (10)	0.1910 (4)	0.5353 (2)	0.0737 (12)
N2	0.5470 (7)	0.2426 (3)	0.80536 (18)	0.0457 (8)
N3	0.5608 (9)	0.1325 (4)	0.9366 (2)	0.0597 (10)
C1	1.1506 (13)	0.0803 (5)	0.5789 (3)	0.0832 (17)
H1B	1.2665	0.0098	0.5544	0.100*
C2	0.9037 (14)	0.2874 (5)	0.5702 (3)	0.0819 (17)
H2B	0.8459	0.3649	0.5403	0.098*
C3	0.7973 (11)	0.2779 (4)	0.6488 (3)	0.0635 (13)
H3B	0.6757	0.3490	0.6713	0.076*
C4	0.8710 (10)	0.1634 (4)	0.6942 (2)	0.0506 (10)
C5	1.0591 (12)	0.0636 (5)	0.6570 (3)	0.0693 (14)
H5A	1.1230	−0.0148	0.6854	0.083*
C6	0.7669 (10)	0.1494 (4)	0.7790 (2)	0.0470 (10)
C7	0.4682 (9)	0.2307 (4)	0.8824 (2)	0.0462 (10)
C8	0.7742 (11)	0.0419 (4)	0.9077 (2)	0.0577 (12)
H8A	0.8544	−0.0276	0.9425	0.069*
C9	0.8839 (10)	0.0436 (4)	0.8303 (3)	0.0558 (11)
H9A	1.0315	−0.0232	0.8123	0.067*
C10	0.0460 (9)	0.4535 (4)	0.8386 (3)	0.0566 (11)
H10A	0.0430	0.4012	0.7912	0.068*
H10B	−0.1644	0.4929	0.8493	0.068*
C11	0.2261 (8)	0.5595 (4)	0.8179 (2)	0.0449 (9)
C12	0.3212 (9)	0.5779 (4)	0.7389 (2)	0.0448 (9)
H12A	0.2784	0.5227	0.6991	0.054*
C13	0.4809 (10)	0.6787 (4)	0.7186 (2)	0.0516 (11)
C14	0.5392 (10)	0.7623 (4)	0.7761 (2)	0.0516 (10)
H14A	0.6428	0.8305	0.7619	0.062*
C15	0.4440 (10)	0.7455 (4)	0.8553 (3)	0.0544 (11)
H15A	0.4859	0.8015	0.8948	0.065*
C16	0.2852 (10)	0.6446 (4)	0.8758 (3)	0.0575 (12)
H16A	0.2182	0.6343	0.9290	0.069*
C17	0.5941 (11)	0.6869 (4)	0.6328 (3)	0.0579 (12)

	U11	U22	U33	U12	U13	U23
S	0.0761 (8)	0.0604 (8)	0.0493 (7)	−0.0024 (6)	0.0165 (5)	0.0109 (5)
O1	0.161 (4)	0.067 (2)	0.0460 (19)	−0.016 (2)	0.026 (2)	−0.0079 (18)
O2	0.125 (3)	0.060 (2)	0.054 (2)	−0.019 (2)	0.0138 (19)	0.0092 (16)
N1	0.104 (3)	0.062 (3)	0.051 (2)	0.000 (2)	0.025 (2)	0.003 (2)
N2	0.056 (2)	0.0419 (19)	0.0373 (18)	−0.0057 (16)	0.0016 (15)	0.0116 (14)
N3	0.087 (3)	0.049 (2)	0.040 (2)	−0.006 (2)	−0.0012 (18)	0.0092 (17)
C1	0.119 (5)	0.054 (3)	0.067 (3)	0.015 (3)	0.027 (3)	0.000 (3)
C2	0.136 (5)	0.057 (3)	0.042 (3)	0.012 (3)	0.011 (3)	0.013 (2)
C3	0.091 (4)	0.048 (3)	0.047 (3)	0.002 (2)	0.010 (2)	0.005 (2)
C4	0.063 (3)	0.041 (2)	0.045 (2)	−0.002 (2)	−0.0035 (19)	0.0036 (18)
C5	0.094 (4)	0.054 (3)	0.051 (3)	0.013 (3)	0.017 (2)	0.011 (2)
C6	0.062 (3)	0.039 (2)	0.039 (2)	−0.007 (2)	−0.0010 (18)	0.0058 (17)
C7	0.056 (2)	0.041 (2)	0.041 (2)	−0.0115 (19)	0.0064 (18)	0.0108 (18)
C8	0.085 (3)	0.046 (3)	0.040 (2)	−0.007 (2)	−0.010 (2)	0.013 (2)
C9	0.074 (3)	0.037 (2)	0.052 (3)	0.004 (2)	−0.002 (2)	0.0017 (19)
C10	0.040 (2)	0.060 (3)	0.065 (3)	0.001 (2)	0.007 (2)	0.009 (2)
C11	0.033 (2)	0.046 (2)	0.051 (2)	0.0036 (17)	−0.0046 (17)	0.0045 (19)
C12	0.049 (2)	0.041 (2)	0.040 (2)	0.0058 (18)	−0.0048 (17)	0.0020 (17)
C13	0.064 (3)	0.040 (2)	0.044 (2)	0.011 (2)	−0.0021 (19)	0.0105 (19)
C14	0.065 (3)	0.039 (2)	0.048 (2)	0.000 (2)	0.001 (2)	0.0047 (19)
C15	0.069 (3)	0.043 (2)	0.049 (3)	−0.002 (2)	−0.006 (2)	−0.0028 (19)
C16	0.064 (3)	0.060 (3)	0.040 (2)	0.016 (2)	0.008 (2)	0.002 (2)
C17	0.074 (3)	0.044 (3)	0.050 (3)	0.005 (2)	0.001 (2)	0.010 (2)

S—C7	1.759 (4)	C5—H5A	0.9300
S—C10	1.809 (4)	C6—C9	1.393 (5)
O1—C17	1.191 (5)	C8—C9	1.360 (6)
O2—C17	1.314 (5)	C8—H8A	0.9300
O2—H2A	0.8200	C9—H9A	0.9300
N1—C2	1.327 (6)	C10—C11	1.496 (6)
N1—C1	1.327 (6)	C10—H10A	0.9700
N2—C7	1.318 (5)	C10—H10B	0.9700
N2—C6	1.341 (5)	C11—C12	1.379 (5)
N3—C8	1.323 (5)	C11—C16	1.382 (6)
N3—C7	1.344 (5)	C12—C13	1.392 (6)
C1—C5	1.358 (6)	C12—H12A	0.9300
C1—H1B	0.9300	C13—C14	1.365 (6)
C2—C3	1.380 (6)	C13—C17	1.499 (6)
C2—H2B	0.9300	C14—C15	1.381 (5)
C3—C4	1.378 (5)	C14—H14A	0.9300
C3—H3B	0.9300	C15—C16	1.390 (6)
C4—C5	1.383 (6)	C15—H15A	0.9300
C4—C6	1.476 (5)	C16—H16A	0.9300
C7—S—C10	103.54 (19)	C8—C9—H9A	121.3
C17—O2—H2A	109.5	C6—C9—H9A	121.3
C2—N1—C1	116.5 (4)	C11—C10—S	116.1 (3)
C7—N2—C6	115.9 (3)	C11—C10—H10A	108.3
C8—N3—C7	113.1 (3)	S—C10—H10A	108.3
N1—C1—C5	124.1 (4)	C11—C10—H10B	108.3
N1—C1—H1B	118.0	S—C10—H10B	108.3
C5—C1—H1B	118.0	H10A—C10—H10B	107.4
N1—C2—C3	123.0 (4)	C12—C11—C16	118.9 (4)
N1—C2—H2B	118.5	C12—C11—C10	120.0 (4)
C3—C2—H2B	118.5	C16—C11—C10	121.0 (4)
C4—C3—C2	120.1 (4)	C11—C12—C13	120.4 (4)
C4—C3—H3B	119.9	C11—C12—H12A	119.8
C2—C3—H3B	119.9	C13—C12—H12A	119.8
C3—C4—C5	116.3 (4)	C14—C13—C12	120.4 (4)
C3—C4—C6	122.1 (4)	C14—C13—C17	122.4 (4)
C5—C4—C6	121.6 (4)	C12—C13—C17	117.1 (4)
C1—C5—C4	119.9 (4)	C13—C14—C15	119.8 (4)
C1—C5—H5A	120.1	C13—C14—H14A	120.1
C4—C5—H5A	120.1	C15—C14—H14A	120.1
N2—C6—C9	120.2 (4)	C14—C15—C16	119.8 (4)
N2—C6—C4	117.1 (3)	C14—C15—H15A	120.1
C9—C6—C4	122.6 (4)	C16—C15—H15A	120.1
N2—C7—N3	128.7 (4)	C11—C16—C15	120.6 (4)
N2—C7—S	120.5 (3)	C11—C16—H16A	119.7
N3—C7—S	110.6 (3)	C15—C16—H16A	119.7
N3—C8—C9	124.3 (4)	O1—C17—O2	122.4 (4)
N3—C8—H8A	117.9	O1—C17—C13	124.5 (4)
C9—C8—H8A	117.9	O2—C17—C13	113.0 (4)
C8—C9—C6	117.5 (4)
C2—N1—C1—C5	−3.9 (9)	N3—C8—C9—C6	1.3 (7)
C1—N1—C2—C3	2.9 (9)	N2—C6—C9—C8	−2.2 (6)
N1—C2—C3—C4	−1.9 (9)	C4—C6—C9—C8	179.0 (4)
C2—C3—C4—C5	1.6 (7)	C7—S—C10—C11	−84.7 (3)
C2—C3—C4—C6	178.9 (5)	S—C10—C11—C12	129.7 (3)
N1—C1—C5—C4	3.9 (9)	S—C10—C11—C16	−53.9 (5)
C3—C4—C5—C1	−2.5 (8)	C16—C11—C12—C13	1.6 (5)
C6—C4—C5—C1	−179.9 (5)	C10—C11—C12—C13	178.1 (4)
C7—N2—C6—C9	4.1 (6)	C11—C12—C13—C14	−1.5 (6)
C7—N2—C6—C4	−177.0 (4)	C11—C12—C13—C17	176.1 (4)
C3—C4—C6—N2	13.3 (6)	C12—C13—C14—C15	1.1 (6)
C5—C4—C6—N2	−169.5 (4)	C17—C13—C14—C15	−176.3 (4)
C3—C4—C6—C9	−167.9 (4)	C13—C14—C15—C16	−1.0 (6)
C5—C4—C6—C9	9.3 (7)	C12—C11—C16—C15	−1.4 (6)
C6—N2—C7—N3	−5.8 (6)	C10—C11—C16—C15	−177.8 (4)
C6—N2—C7—S	179.7 (3)	C14—C15—C16—C11	1.1 (6)
C8—N3—C7—N2	4.8 (7)	C14—C13—C17—O1	163.6 (5)
C8—N3—C7—S	179.7 (3)	C12—C13—C17—O1	−14.0 (7)
C10—S—C7—N2	4.9 (4)	C14—C13—C17—O2	−12.5 (6)
C10—S—C7—N3	−170.5 (3)	C12—C13—C17—O2	170.0 (4)
C7—N3—C8—C9	−2.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1i	0.82	1.84	2.659 (5)	174
C10—H10B···Cg3ii	0.97	2.56	3.398 (5)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1i	0.82	1.84	2.659 (5)	174
C10—H10B⋯Cg3ii	0.97	2.56	3.398 (5)	145

Symmetry codes: (i) ; (ii) . Cg3 is the centroid of the phenyl ring.