4,6-Dimeth-oxy-2-(methyl-sulfan-yl)pyrimidine.

The title compound, C(7)H(10)N(2)O(2)S, is essentially planar [maximum deviation 0.018 (4) Å]. In the crystal, mol-ecules are linked into chains by C-H⋯N hydrogen bonds and the chains are arranged in layers parallel to the ab plane.

Related literature

For general background to substituted pyrimidines, see: Salas et al. (1995 ▶); Holy et al. (1974 ▶); Hunt et al. (1980 ▶); Baker & Santi, (1965 ▶) For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C7H10N2O2S

M = 186.23

Orthorhombic,

a = 3.9537 (2) Å

b = 7.1822 (4) Å

c = 30.5723 (15) Å

V = 868.14 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 100 K

0.55 × 0.31 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.838, T max = 0.985

4467 measured reflections

1620 independent reflections

1555 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.133

S = 1.28

1620 reflections

112 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 584 Friedel pairs

Flack parameter: 0.2 (2)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027263/ci2850sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027263/ci2850Isup2.hkl

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

C7H10N2O2S	F(000) = 392
Mr = 186.23	Dx = 1.425 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3133 reflections
a = 3.9537 (2) Å	θ = 2.7–30.7°
b = 7.1822 (4) Å	µ = 0.33 mm−1
c = 30.5723 (15) Å	T = 100 K
V = 868.14 (8) Å3	Plate, yellow
Z = 4	0.55 × 0.31 × 0.05 mm

Bruker SMART APEXII CCD area-detector diffractometer	1620 independent reflections
Radiation source: fine-focus sealed tube	1555 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 26.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −4→4
Tmin = 0.838, Tmax = 0.985	k = −6→8
4467 measured reflections	l = −37→37

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + 2.7239P] where P = (Fo2 + 2Fc2)/3
S = 1.28	(Δ/σ)max = 0.001
1620 reflections	Δρmax = 0.42 e Å−3
112 parameters	Δρmin = −0.47 e Å−3
0 restraints	Absolute structure: Flack (1983), 584 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.2 (2)

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
S1	0.6163 (3)	0.16537 (16)	0.05410 (4)	0.0194 (3)
O1	0.7269 (9)	0.2088 (4)	0.21365 (10)	0.0207 (8)
O2	1.1384 (9)	−0.3287 (4)	0.14636 (9)	0.0200 (7)
N1	0.6864 (9)	0.1795 (5)	0.13848 (11)	0.0140 (8)
N2	0.8979 (11)	−0.0980 (5)	0.10377 (11)	0.0177 (8)
C1	0.7499 (12)	0.0691 (6)	0.10392 (14)	0.0163 (9)
C2	0.9874 (12)	−0.1607 (7)	0.14346 (14)	0.0190 (10)
C3	0.9362 (12)	−0.0645 (6)	0.18210 (14)	0.0184 (10)
H3A	0.9998	−0.1113	0.2092	0.022*
C4	0.7818 (11)	0.1081 (7)	0.17698 (13)	0.0159 (9)
C5	0.7262 (13)	−0.0160 (7)	0.01606 (14)	0.0206 (10)
H5A	0.6651	0.0217	−0.0130	0.031*
H5B	0.6069	−0.1279	0.0236	0.031*
H5C	0.9653	−0.0385	0.0173	0.031*
C6	0.5624 (13)	0.3873 (6)	0.20817 (14)	0.0200 (10)
H6A	0.5276	0.4436	0.2363	0.030*
H6B	0.3481	0.3699	0.1940	0.030*
H6C	0.7023	0.4670	0.1906	0.030*
C7	1.1937 (13)	−0.4273 (7)	0.10586 (14)	0.0210 (11)
H7A	1.3211	−0.5385	0.1115	0.032*
H7B	1.3170	−0.3492	0.0860	0.032*
H7C	0.9797	−0.4598	0.0931	0.032*

	U11	U22	U33	U12	U13	U23
S1	0.0226 (6)	0.0161 (5)	0.0194 (5)	0.0009 (6)	−0.0013 (5)	0.0026 (5)
O1	0.0265 (19)	0.0147 (16)	0.0207 (15)	0.0071 (14)	0.0014 (14)	−0.0017 (12)
O2	0.0249 (17)	0.0127 (14)	0.0225 (14)	0.0059 (18)	0.0005 (14)	0.0001 (13)
N1	0.0059 (18)	0.0141 (17)	0.0221 (17)	−0.0036 (16)	0.0012 (13)	0.0001 (15)
N2	0.019 (2)	0.0143 (17)	0.0200 (17)	0.0012 (19)	−0.0030 (17)	0.0004 (14)
C1	0.019 (2)	0.012 (2)	0.019 (2)	−0.006 (2)	−0.0011 (19)	0.0031 (16)
C2	0.018 (2)	0.016 (2)	0.023 (2)	0.000 (2)	0.0023 (17)	0.005 (2)
C3	0.020 (3)	0.016 (2)	0.019 (2)	0.001 (2)	0.0027 (19)	0.0040 (18)
C4	0.010 (2)	0.019 (2)	0.018 (2)	−0.0014 (19)	0.0056 (17)	0.0014 (17)
C5	0.017 (3)	0.024 (2)	0.021 (2)	0.001 (2)	−0.0007 (19)	0.0000 (19)
C6	0.022 (3)	0.012 (2)	0.026 (2)	0.010 (2)	0.003 (2)	−0.0018 (18)
C7	0.021 (3)	0.017 (2)	0.026 (2)	0.007 (2)	−0.0007 (19)	−0.0013 (18)

S1—C1	1.754 (4)	C3—C4	1.390 (7)
S1—C5	1.799 (5)	C3—H3A	0.93
O1—C4	1.352 (5)	C5—H5A	0.96
O1—C6	1.448 (5)	C5—H5B	0.96
O2—C2	1.349 (6)	C5—H5C	0.96
O2—C7	1.443 (5)	C6—H6A	0.96
N1—C4	1.338 (5)	C6—H6B	0.96
N1—C1	1.345 (6)	C6—H6C	0.96
N2—C1	1.335 (6)	C7—H7A	0.96
N2—C2	1.342 (6)	C7—H7B	0.96
C2—C3	1.384 (6)	C7—H7C	0.96
C1—S1—C5	101.7 (2)	S1—C5—H5B	109.5
C4—O1—C6	116.8 (3)	H5A—C5—H5B	109.5
C2—O2—C7	116.7 (3)	S1—C5—H5C	109.5
C4—N1—C1	114.4 (4)	H5A—C5—H5C	109.5
C1—N2—C2	114.5 (4)	H5B—C5—H5C	109.5
N2—C1—N1	127.9 (4)	O1—C6—H6A	109.5
N2—C1—S1	118.9 (3)	O1—C6—H6B	109.5
N1—C1—S1	113.2 (3)	H6A—C6—H6B	109.5
N2—C2—O2	118.4 (4)	O1—C6—H6C	109.5
N2—C2—C3	124.5 (4)	H6A—C6—H6C	109.5
O2—C2—C3	117.1 (4)	H6B—C6—H6C	109.5
C2—C3—C4	114.4 (4)	O2—C7—H7A	109.5
C2—C3—H3A	122.8	O2—C7—H7B	109.5
C4—C3—H3A	122.8	H7A—C7—H7B	109.5
N1—C4—O1	118.6 (4)	O2—C7—H7C	109.5
N1—C4—C3	124.4 (4)	H7A—C7—H7C	109.5
O1—C4—C3	117.0 (4)	H7B—C7—H7C	109.5
S1—C5—H5A	109.5
C2—N2—C1—N1	0.9 (7)	C7—O2—C2—C3	−179.4 (4)
C2—N2—C1—S1	−179.3 (3)	N2—C2—C3—C4	−0.3 (7)
C4—N1—C1—N2	−1.1 (7)	O2—C2—C3—C4	179.6 (4)
C4—N1—C1—S1	179.1 (3)	C1—N1—C4—O1	−179.7 (4)
C5—S1—C1—N2	1.6 (4)	C1—N1—C4—C3	0.4 (6)
C5—S1—C1—N1	−178.5 (3)	C6—O1—C4—N1	0.9 (6)
C1—N2—C2—O2	179.9 (4)	C6—O1—C4—C3	−179.3 (4)
C1—N2—C2—C3	−0.2 (7)	C2—C3—C4—N1	0.1 (7)
C7—O2—C2—N2	0.4 (6)	C2—C3—C4—O1	−179.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N1i	0.96	2.62	3.573 (6)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯N1i	0.96	2.62	3.573 (6)	171

Symmetry code: (i) .