Ethyl 2-{[4-(pyridin-4-yl)pyrimidin-2-yl]sulfan-yl}acetate.

In the title mol-ecule, C(13)H(13)N(3)O(2)S, the pyridine and pyrimidine rings form a dihedral angle of 3.8 (1)°. The crystal packing exhibits weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For details of the synthesis and general background to the rational design and assembly of coordination polymers with thio­ethers, see: Dong et al. (2008 ▶, 2009 ▶). For the crystal structures of coordination complexes with related ligands, see: Du et al. (2004 ▶); Zhu et al. (2009 ▶).

Experimental

Crystal data

C13H13N3O2S

M = 275.33

Triclinic,

a = 8.6579 (8) Å

b = 9.7394 (9) Å

c = 9.9188 (8) Å

α = 62.661 (6)°

β = 71.416 (5)°

γ = 65.024 (6)°

V = 665.35 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 291 K

0.32 × 0.24 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.917, T max = 0.966

11760 measured reflections

3021 independent reflections

2387 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.115

S = 1.04

3021 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 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 datablocks I, global. DOI: 10.1107/S1600536811004272/cv5047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004272/cv5047Isup2.hkl

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

C13H13N3O2S	Z = 2
Mr = 275.33	F(000) = 288.0
Triclinic, P1	Dx = 1.374 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6579 (8) Å	Cell parameters from 3021 reflections
b = 9.7394 (9) Å	θ = 2.3–27.5°
c = 9.9188 (8) Å	µ = 0.25 mm−1
α = 62.661 (6)°	T = 291 K
β = 71.416 (5)°	Block, colorless
γ = 65.024 (6)°	0.32 × 0.24 × 0.18 mm
V = 665.35 (10) Å3

Bruker SMART CCD area-detector diffractometer	3021 independent reflections
Radiation source: fine-focus sealed tube	2387 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→10
Tmin = 0.917, Tmax = 0.966	k = −12→12
11760 measured reflections	l = −12→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0658P)2 + 0.067P] where P = (Fo2 + 2Fc2)/3
3021 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.20 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	0.21141 (18)	0.00339 (18)	0.89933 (17)	0.0411 (3)
C2	0.3174 (2)	−0.21822 (19)	1.10105 (19)	0.0496 (4)
H2	0.3517	−0.3308	1.1555	0.060*
C3	0.3336 (2)	−0.12042 (18)	1.15846 (18)	0.0459 (4)
H3	0.3793	−0.1652	1.2484	0.055*
C4	0.27871 (17)	0.04721 (17)	1.07653 (16)	0.0376 (3)
C5	0.28647 (18)	0.16653 (17)	1.12645 (16)	0.0388 (3)
C6	0.3582 (2)	0.1176 (2)	1.25464 (18)	0.0478 (4)
H6	0.4018	0.0070	1.3141	0.057*
C7	0.3641 (2)	0.2347 (2)	1.2930 (2)	0.0568 (4)
H7	0.4126	0.1991	1.3794	0.068*
C8	0.2241 (2)	0.3332 (2)	1.04370 (19)	0.0525 (4)
H8	0.1740	0.3725	0.9573	0.063*
C9	0.2372 (3)	0.4407 (2)	1.0913 (2)	0.0660 (5)
H9	0.1960	0.5521	1.0335	0.079*
C10	0.0836 (2)	0.2913 (2)	0.6641 (2)	0.0515 (4)
H10A	0.0315	0.3439	0.5718	0.062*
H10B	−0.0042	0.3227	0.7439	0.062*
C11	0.2273 (2)	0.35667 (18)	0.63290 (16)	0.0422 (3)
C12	0.2788 (2)	0.5879 (2)	0.6083 (2)	0.0620 (5)
H12A	0.3426	0.6012	0.5056	0.074*
H12B	0.3603	0.5258	0.6805	0.074*
C13	0.1774 (3)	0.7498 (3)	0.6187 (3)	0.0927 (8)
H13A	0.1014	0.8124	0.5432	0.139*
H13B	0.2542	0.8066	0.6002	0.139*
H13C	0.1108	0.7354	0.7193	0.139*
N1	0.3051 (2)	0.39441 (19)	1.21466 (18)	0.0644 (4)
N2	0.21695 (15)	0.11055 (14)	0.94434 (14)	0.0392 (3)
N3	0.25523 (17)	−0.15909 (16)	0.97173 (16)	0.0482 (3)
O1	0.37818 (15)	0.29263 (14)	0.59842 (13)	0.0516 (3)
O2	0.15904 (14)	0.50272 (13)	0.64426 (13)	0.0512 (3)
S1	0.14603 (6)	0.07492 (5)	0.72151 (5)	0.05259 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0408 (8)	0.0366 (8)	0.0520 (8)	−0.0153 (6)	−0.0068 (6)	−0.0197 (6)
C2	0.0542 (9)	0.0320 (8)	0.0601 (10)	−0.0176 (7)	−0.0095 (7)	−0.0119 (7)
C3	0.0514 (9)	0.0366 (8)	0.0489 (8)	−0.0168 (7)	−0.0111 (7)	−0.0113 (7)
C4	0.0365 (7)	0.0348 (7)	0.0428 (7)	−0.0142 (6)	−0.0023 (6)	−0.0159 (6)
C5	0.0402 (8)	0.0373 (8)	0.0415 (7)	−0.0142 (6)	−0.0015 (6)	−0.0188 (6)
C6	0.0573 (9)	0.0410 (8)	0.0463 (8)	−0.0143 (7)	−0.0124 (7)	−0.0162 (7)
C7	0.0713 (11)	0.0575 (11)	0.0533 (9)	−0.0186 (9)	−0.0167 (8)	−0.0282 (8)
C8	0.0712 (11)	0.0398 (9)	0.0521 (9)	−0.0135 (8)	−0.0201 (8)	−0.0192 (7)
C9	0.1000 (15)	0.0390 (9)	0.0678 (11)	−0.0152 (9)	−0.0285 (10)	−0.0238 (8)
C10	0.0549 (9)	0.0403 (8)	0.0677 (10)	−0.0094 (7)	−0.0271 (8)	−0.0213 (8)
C11	0.0533 (9)	0.0353 (8)	0.0405 (7)	−0.0108 (7)	−0.0175 (6)	−0.0130 (6)
C12	0.0637 (11)	0.0517 (10)	0.0791 (12)	−0.0294 (9)	−0.0024 (9)	−0.0277 (9)
C13	0.0989 (17)	0.0653 (14)	0.133 (2)	−0.0416 (13)	0.0127 (15)	−0.0589 (15)
N1	0.0889 (11)	0.0530 (9)	0.0664 (9)	−0.0200 (8)	−0.0205 (8)	−0.0321 (8)
N2	0.0434 (7)	0.0334 (6)	0.0460 (7)	−0.0143 (5)	−0.0076 (5)	−0.0172 (5)
N3	0.0534 (8)	0.0346 (7)	0.0629 (8)	−0.0176 (6)	−0.0102 (6)	−0.0199 (6)
O1	0.0513 (7)	0.0473 (7)	0.0572 (7)	−0.0104 (5)	−0.0108 (5)	−0.0241 (5)
O2	0.0521 (6)	0.0386 (6)	0.0680 (7)	−0.0148 (5)	−0.0100 (5)	−0.0237 (5)
S1	0.0670 (3)	0.0416 (2)	0.0651 (3)	−0.0161 (2)	−0.0253 (2)	−0.0246 (2)

C1—N2	1.3323 (17)	C8—H8	0.9300
C1—N3	1.3367 (19)	C9—N1	1.332 (2)
C1—S1	1.7582 (16)	C9—H9	0.9300
C2—N3	1.329 (2)	C10—C11	1.514 (2)
C2—C3	1.383 (2)	C10—S1	1.7858 (16)
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.387 (2)	C10—H10B	0.9700
C3—H3	0.9300	C11—O1	1.1984 (18)
C4—N2	1.3456 (18)	C11—O2	1.3342 (17)
C4—C5	1.4886 (19)	C12—O2	1.4529 (19)
C5—C8	1.385 (2)	C12—C13	1.479 (3)
C5—C6	1.388 (2)	C12—H12A	0.9700
C6—C7	1.381 (2)	C12—H12B	0.9700
C6—H6	0.9300	C13—H13A	0.9600
C7—N1	1.325 (2)	C13—H13B	0.9600
C7—H7	0.9300	C13—H13C	0.9600
C8—C9	1.385 (2)
N2—C1—N3	127.86 (14)	C11—C10—S1	115.61 (11)
N2—C1—S1	118.93 (11)	C11—C10—H10A	108.4
N3—C1—S1	113.18 (10)	S1—C10—H10A	108.4
N3—C2—C3	123.15 (14)	C11—C10—H10B	108.4
N3—C2—H2	118.4	S1—C10—H10B	108.4
C3—C2—H2	118.4	H10A—C10—H10B	107.4
C2—C3—C4	117.32 (15)	O1—C11—O2	124.33 (14)
C2—C3—H3	121.3	O1—C11—C10	126.61 (14)
C4—C3—H3	121.3	O2—C11—C10	109.02 (13)
N2—C4—C3	120.88 (13)	O2—C12—C13	107.85 (15)
N2—C4—C5	116.22 (12)	O2—C12—H12A	110.1
C3—C4—C5	122.90 (13)	C13—C12—H12A	110.1
C8—C5—C6	116.98 (13)	O2—C12—H12B	110.1
C8—C5—C4	120.72 (13)	C13—C12—H12B	110.1
C6—C5—C4	122.29 (13)	H12A—C12—H12B	108.5
C7—C6—C5	119.32 (15)	C12—C13—H13A	109.5
C7—C6—H6	120.3	C12—C13—H13B	109.5
C5—C6—H6	120.3	H13A—C13—H13B	109.5
N1—C7—C6	124.28 (16)	C12—C13—H13C	109.5
N1—C7—H7	117.9	H13A—C13—H13C	109.5
C6—C7—H7	117.9	H13B—C13—H13C	109.5
C9—C8—C5	119.20 (15)	C7—N1—C9	116.14 (14)
C9—C8—H8	120.4	C1—N2—C4	116.09 (12)
C5—C8—H8	120.4	C2—N3—C1	114.65 (12)
N1—C9—C8	124.07 (17)	C11—O2—C12	116.28 (12)
N1—C9—H9	118.0	C1—S1—C10	101.64 (7)
C8—C9—H9	118.0

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.52	3.383 (2)	154
C7—H7···O1ii	0.93	2.61	3.373 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.52	3.383 (2)	154
C7—H7⋯O1ii	0.93	2.61	3.373 (2)	140

Symmetry codes: (i) ; (ii) .