2-[(2-Meth-oxy-eth-yl)sulfan-yl]-4-(2-methyl-prop-yl)-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile.

In the title compound, C(12)H(17)N(3)O(2)S, the 4-methyl-2-methyl-sulfanyl-6-oxo-1,6-dihydro-pyrimidine-5-carbonitrile part of the mol-ecule is almost planar (r.m.s deviation = 0.062 Å). In the crystal, mol-ecules form centrosymmetric dimers via pairs of N-H⋯O hydrogen bonds.

Related literature

For related pyrimidine structures, see: Yan et al. (2011 ▶); El-Brollosy et al. (2011 ▶); Nasir et al. (2010 ▶); Tiekink (1989 ▶); Al-Deeb et al. (2012 ▶); Durkaya et al. (2011 ▶).

Experimental

Crystal data

C12H17N3O2S

M = 267.35

Triclinic,

a = 5.0379 (5) Å

b = 10.5453 (10) Å

c = 13.3936 (13) Å

α = 85.274 (8)°

β = 82.170 (8)°

γ = 83.034 (8)°

V = 698.14 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.68 × 0.47 × 0.15 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.859, T max = 0.966

6663 measured reflections

2725 independent reflections

2090 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.126

S = 1.02

2725 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.22 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: WinGX (Farrugia, 1997 ▶) and SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013372/bt5854sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013372/bt5854Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013372/bt5854Isup3.cml

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

C12H17N3O2S	Z = 2
Mr = 267.35	F(000) = 284
Triclinic, P1	Dx = 1.272 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0379 (5) Å	Cell parameters from 9417 reflections
b = 10.5453 (10) Å	θ = 3.1–27.9°
c = 13.3936 (13) Å	µ = 0.23 mm−1
α = 85.274 (8)°	T = 296 K
β = 82.170 (8)°	Prism, colorless
γ = 83.034 (8)°	0.68 × 0.47 × 0.15 mm
V = 698.14 (12) Å3

Stoe IPDS 2 diffractometer	2725 independent reflections
Radiation source: fine-focus sealed tube	2090 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
rotation method scans	θmax = 26.0°, θmin = 3.1°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −6→6
Tmin = 0.859, Tmax = 0.966	k = −12→12
6663 measured reflections	l = −16→16

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0743P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2725 reflections	Δρmax = 0.28 e Å−3
164 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.059 (9)

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	0.6121 (4)	0.32542 (17)	0.13412 (14)	0.0433 (4)
C2	0.9074 (4)	0.48214 (16)	0.15109 (15)	0.0450 (4)
C3	0.8266 (4)	0.46228 (16)	0.25758 (15)	0.0442 (4)
C4	0.6474 (4)	0.37554 (16)	0.29360 (14)	0.0437 (4)
C5	0.9463 (4)	0.53342 (18)	0.32209 (16)	0.0520 (5)
C6	0.5689 (4)	0.34539 (18)	0.40400 (14)	0.0495 (5)
H6A	0.3788	0.3735	0.4212	0.059*
H6B	0.6694	0.3929	0.4421	0.059*
C7	0.6216 (4)	0.20252 (19)	0.43492 (15)	0.0479 (4)
H7	0.5092	0.1569	0.3991	0.057*
C8	0.5377 (5)	0.1782 (2)	0.54676 (17)	0.0632 (6)
H8A	0.3491	0.2060	0.5625	0.076*
H8B	0.6398	0.2249	0.5837	0.076*
H8C	0.5710	0.0883	0.5652	0.076*
C9	0.9103 (5)	0.1502 (3)	0.4063 (2)	0.0851 (9)
H9A	1.0253	0.1946	0.4393	0.102*
H9B	0.9561	0.1620	0.3344	0.102*
H9C	0.9339	0.0606	0.4267	0.102*
C10	0.3129 (4)	0.1261 (2)	0.12329 (17)	0.0566 (5)
H10A	0.1835	0.1737	0.1707	0.068*
H10B	0.2118	0.0853	0.0808	0.068*
C11	0.4729 (5)	0.0231 (2)	0.18197 (18)	0.0646 (6)
H11A	0.5673	0.0621	0.2278	0.078*
H11B	0.3517	−0.0319	0.2218	0.078*
C12	0.7991 (8)	−0.1519 (3)	0.1697 (3)	0.1020 (10)
H12A	0.6742	−0.2072	0.2050	0.122*
H12B	0.8951	−0.1190	0.2173	0.122*
H12C	0.9246	−0.1993	0.1222	0.122*
N1	0.7874 (3)	0.40967 (14)	0.09326 (12)	0.0468 (4)
H1	0.8246	0.4179	0.0286	0.056*
N2	0.5378 (3)	0.30759 (14)	0.23047 (12)	0.0452 (4)
N3	1.0420 (5)	0.5910 (2)	0.37314 (18)	0.0761 (6)
O1	1.0717 (3)	0.55469 (13)	0.11167 (11)	0.0575 (4)
O2	0.6562 (4)	−0.04885 (17)	0.11760 (15)	0.0855 (6)
S1	0.50676 (11)	0.23771 (5)	0.04486 (4)	0.0547 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0492 (9)	0.0408 (9)	0.0385 (10)	−0.0040 (7)	−0.0042 (8)	0.0019 (7)
C2	0.0564 (10)	0.0373 (9)	0.0396 (10)	−0.0048 (7)	−0.0018 (8)	0.0007 (7)
C3	0.0553 (10)	0.0365 (9)	0.0393 (10)	−0.0011 (7)	−0.0048 (8)	−0.0003 (7)
C4	0.0518 (10)	0.0375 (8)	0.0388 (10)	0.0004 (7)	−0.0015 (8)	−0.0005 (7)
C5	0.0637 (12)	0.0444 (10)	0.0473 (11)	−0.0056 (8)	−0.0067 (9)	−0.0014 (9)
C6	0.0616 (11)	0.0483 (10)	0.0365 (10)	−0.0073 (8)	0.0017 (8)	−0.0027 (8)
C7	0.0479 (10)	0.0544 (10)	0.0402 (10)	−0.0077 (8)	−0.0033 (8)	0.0033 (8)
C8	0.0734 (14)	0.0715 (14)	0.0423 (12)	−0.0143 (11)	0.0004 (10)	0.0074 (10)
C9	0.0608 (14)	0.103 (2)	0.0744 (18)	0.0151 (13)	0.0095 (12)	0.0300 (16)
C10	0.0606 (12)	0.0580 (12)	0.0512 (12)	−0.0167 (9)	0.0002 (9)	−0.0007 (9)
C11	0.0896 (16)	0.0523 (11)	0.0507 (13)	−0.0130 (11)	−0.0013 (11)	−0.0013 (10)
C12	0.127 (3)	0.0788 (18)	0.096 (3)	0.0192 (17)	−0.029 (2)	−0.0031 (17)
N1	0.0598 (9)	0.0449 (8)	0.0347 (8)	−0.0099 (7)	−0.0015 (7)	0.0027 (6)
N2	0.0537 (8)	0.0448 (8)	0.0357 (8)	−0.0073 (6)	−0.0008 (7)	0.0007 (6)
N3	0.0948 (15)	0.0671 (12)	0.0729 (15)	−0.0169 (11)	−0.0209 (12)	−0.0147 (11)
O1	0.0751 (9)	0.0526 (8)	0.0456 (8)	−0.0238 (7)	0.0009 (7)	0.0019 (6)
O2	0.1202 (15)	0.0712 (11)	0.0588 (11)	0.0131 (10)	−0.0080 (10)	−0.0074 (9)
S1	0.0701 (4)	0.0594 (3)	0.0368 (3)	−0.0201 (2)	−0.0053 (2)	−0.0007 (2)

C1—N2	1.299 (2)	C8—H8B	0.9600
C1—N1	1.359 (2)	C8—H8C	0.9600
C1—S1	1.744 (2)	C9—H9A	0.9600
C2—O1	1.232 (2)	C9—H9B	0.9600
C2—N1	1.374 (2)	C9—H9C	0.9600
C2—C3	1.434 (3)	C10—C11	1.505 (3)
C3—C4	1.376 (3)	C10—S1	1.800 (2)
C3—C5	1.425 (3)	C10—H10A	0.9700
C4—N2	1.363 (2)	C10—H10B	0.9700
C4—C6	1.496 (3)	C11—O2	1.376 (3)
C5—N3	1.139 (3)	C11—H11A	0.9700
C6—C7	1.530 (3)	C11—H11B	0.9700
C6—H6A	0.9700	C12—O2	1.417 (3)
C6—H6B	0.9700	C12—H12A	0.9600
C7—C9	1.502 (3)	C12—H12B	0.9600
C7—C8	1.510 (3)	C12—H12C	0.9600
C7—H7	0.9800	N1—H1	0.8600
C8—H8A	0.9600
N2—C1—N1	123.67 (18)	C7—C9—H9A	109.5
N2—C1—S1	122.84 (14)	C7—C9—H9B	109.5
N1—C1—S1	113.43 (14)	H9A—C9—H9B	109.5
O1—C2—N1	120.88 (18)	C7—C9—H9C	109.5
O1—C2—C3	125.26 (18)	H9A—C9—H9C	109.5
N1—C2—C3	113.85 (16)	H9B—C9—H9C	109.5
C4—C3—C5	122.88 (18)	C11—C10—S1	115.59 (16)
C4—C3—C2	120.35 (18)	C11—C10—H10A	108.4
C5—C3—C2	116.75 (17)	S1—C10—H10A	108.4
N2—C4—C3	121.83 (17)	C11—C10—H10B	108.4
N2—C4—C6	115.56 (15)	S1—C10—H10B	108.4
C3—C4—C6	122.56 (18)	H10A—C10—H10B	107.4
N3—C5—C3	179.5 (2)	O2—C11—C10	110.6 (2)
C4—C6—C7	112.75 (16)	O2—C11—H11A	109.5
C4—C6—H6A	109.0	C10—C11—H11A	109.5
C7—C6—H6A	109.0	O2—C11—H11B	109.5
C4—C6—H6B	109.0	C10—C11—H11B	109.5
C7—C6—H6B	109.0	H11A—C11—H11B	108.1
H6A—C6—H6B	107.8	O2—C12—H12A	109.5
C9—C7—C8	110.84 (19)	O2—C12—H12B	109.5
C9—C7—C6	112.29 (18)	H12A—C12—H12B	109.5
C8—C7—C6	110.23 (18)	O2—C12—H12C	109.5
C9—C7—H7	107.8	H12A—C12—H12C	109.5
C8—C7—H7	107.8	H12B—C12—H12C	109.5
C6—C7—H7	107.8	C1—N1—C2	122.62 (16)
C7—C8—H8A	109.5	C1—N1—H1	118.7
C7—C8—H8B	109.5	C2—N1—H1	118.7
H8A—C8—H8B	109.5	C1—N2—C4	117.66 (16)
C7—C8—H8C	109.5	C11—O2—C12	112.2 (2)
H8A—C8—H8C	109.5	C1—S1—C10	102.06 (10)
H8B—C8—H8C	109.5
O1—C2—C3—C4	−177.90 (18)	N2—C1—N1—C2	1.5 (3)
N1—C2—C3—C4	0.9 (3)	S1—C1—N1—C2	−175.81 (14)
O1—C2—C3—C5	0.4 (3)	O1—C2—N1—C1	177.75 (17)
N1—C2—C3—C5	179.25 (15)	C3—C2—N1—C1	−1.1 (3)
C5—C3—C4—N2	−179.28 (17)	N1—C1—N2—C4	−1.5 (3)
C2—C3—C4—N2	−1.1 (3)	S1—C1—N2—C4	175.58 (13)
C5—C3—C4—C6	−1.9 (3)	C3—C4—N2—C1	1.3 (3)
C2—C3—C4—C6	176.28 (17)	C6—C4—N2—C1	−176.22 (16)
N2—C4—C6—C7	53.7 (2)	C10—C11—O2—C12	−176.3 (2)
C3—C4—C6—C7	−123.80 (19)	N2—C1—S1—C10	−3.49 (19)
C4—C6—C7—C9	56.1 (3)	N1—C1—S1—C10	173.88 (14)
C4—C6—C7—C8	−179.82 (18)	C11—C10—S1—C1	−70.78 (19)
S1—C10—C11—O2	−59.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.89	2.747 (2)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.89	2.747 (2)	175

Symmetry code: (i) .