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

The asymmetric unit of the title compound, C(7)H(10)N(2)O(4)S, comprises of two independent mol-ecules (A and B) which differ in the orientation of the methyl-sulfonyl group [C-S-C-N = 157.98 (13)° in mol-ecule A and 6.09 (18)° in mol-ecule B]. In the crystal structure, mol-ecules of type A are linked into chains along the a axis by inter-molecular C-H⋯O hydrogen bonds. The B mol-ecules are linked to these chains by C-H⋯O hydrogen bonds.

Related literature

For general background and applications of 4,6-dimeth­oxy­pyrimidin-2-yl derivatives, see: Xi et al. (2006 ▶); He et al. (2007 ▶); Li et al. (2006 ▶); Gerorge (1983 ▶).

Experimental

Crystal data

C7H10N2O4S

M = 218.23

Triclinic,

a = 8.349 (2) Å

b = 11.067 (3) Å

c = 11.438 (3) Å

α = 108.457 (8)°

β = 92.774 (8)°

γ = 98.504 (8)°

V = 986.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.38 × 0.30 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.889, T max = 0.974

29277 measured reflections

7063 independent reflections

4866 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.156

S = 1.08

7063 reflections

259 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536810025067/ci5121sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025067/ci5121Isup2.hkl

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

C7H10N2O4S	Z = 4
Mr = 218.23	F(000) = 456
Triclinic, P1	Dx = 1.470 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.349 (2) Å	Cell parameters from 8362 reflections
b = 11.067 (3) Å	θ = 2.2–32.1°
c = 11.438 (3) Å	µ = 0.32 mm−1
α = 108.457 (8)°	T = 296 K
β = 92.774 (8)°	Plate, colourless
γ = 98.504 (8)°	0.38 × 0.30 × 0.08 mm
V = 986.4 (4) Å3

Bruker APEXII DUO CCD area-detector diffractometer	7063 independent reflections
Radiation source: fine-focus sealed tube	4866 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 32.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.889, Tmax = 0.974	k = −16→16
29277 measured reflections	l = −17→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0771P)2 + 0.1962P] where P = (Fo2 + 2Fc2)/3
7063 reflections	(Δ/σ)max = 0.001
259 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.50 e Å−3

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
S1A	−0.01034 (4)	0.04422 (4)	0.19330 (4)	0.03856 (12)
O1A	−0.02361 (19)	0.10070 (16)	0.32304 (15)	0.0632 (4)
O2A	−0.08995 (15)	0.09457 (13)	0.10934 (15)	0.0518 (3)
O3A	0.50597 (16)	0.29863 (13)	0.14202 (15)	0.0528 (3)
O4A	0.51835 (16)	−0.11116 (13)	0.16945 (16)	0.0543 (3)
N1A	0.26662 (16)	0.17382 (13)	0.16027 (13)	0.0362 (3)
N2A	0.27464 (15)	−0.03547 (13)	0.17789 (13)	0.0364 (3)
C1A	0.20400 (17)	0.06224 (14)	0.17287 (14)	0.0334 (3)
C2A	0.43408 (19)	−0.01755 (16)	0.16718 (16)	0.0386 (3)
C3A	0.51867 (19)	0.09495 (18)	0.15559 (17)	0.0435 (4)
H3AA	0.6304	0.1068	0.1502	0.052*
C4A	0.42742 (19)	0.18858 (16)	0.15246 (15)	0.0378 (3)
C5A	0.4131 (3)	0.3951 (2)	0.1326 (3)	0.0608 (5)
H5AA	0.4838	0.4653	0.1194	0.091*
H5AB	0.3635	0.4268	0.2078	0.091*
H5AC	0.3300	0.3577	0.0642	0.091*
C6A	0.4289 (3)	−0.2300 (2)	0.1768 (3)	0.0630 (6)
H6AA	0.5032	−0.2872	0.1814	0.095*
H6AB	0.3525	−0.2704	0.1045	0.095*
H6AC	0.3714	−0.2116	0.2494	0.095*
C7A	−0.0758 (2)	−0.12239 (17)	0.1485 (2)	0.0476 (4)
H7AA	−0.1909	−0.1400	0.1536	0.071*
H7AB	−0.0197	−0.1571	0.2024	0.071*
H7AC	−0.0529	−0.1618	0.0648	0.071*
S1B	0.91824 (6)	0.54889 (4)	0.18573 (4)	0.04122 (12)
O1B	1.0732 (2)	0.63051 (15)	0.21079 (16)	0.0655 (4)
O2B	0.8041 (2)	0.56321 (17)	0.09628 (13)	0.0639 (4)
O3B	0.7212 (2)	0.42513 (15)	0.54172 (14)	0.0673 (5)
O4B	0.6688 (2)	0.83263 (14)	0.52687 (15)	0.0629 (4)
N1B	0.78624 (19)	0.69578 (14)	0.36974 (14)	0.0437 (3)
N2B	0.81160 (19)	0.48548 (14)	0.37722 (13)	0.0414 (3)
C1B	0.8263 (2)	0.57971 (16)	0.32927 (15)	0.0382 (3)
C2B	0.7173 (2)	0.71868 (18)	0.47615 (17)	0.0471 (4)
C3B	0.6896 (3)	0.6287 (2)	0.53590 (18)	0.0574 (5)
H3BA	0.6383	0.6454	0.6084	0.069*
C4B	0.7415 (3)	0.51237 (18)	0.48331 (17)	0.0479 (4)
C5B	0.7711 (4)	0.3023 (2)	0.4853 (2)	0.0658 (6)
H5BA	0.7710	0.2564	0.5438	0.099*
H5BB	0.8787	0.3163	0.4607	0.099*
H5BC	0.6967	0.2525	0.4138	0.099*
C6B	0.7263 (4)	0.9364 (2)	0.4804 (2)	0.0717 (7)
H6BA	0.7075	1.0168	0.5370	0.108*
H6BB	0.6689	0.9210	0.4009	0.108*
H6BC	0.8408	0.9406	0.4725	0.108*
C7B	0.9425 (3)	0.38667 (19)	0.1441 (2)	0.0596 (6)
H7BA	0.9860	0.3620	0.0655	0.089*
H7BB	0.8389	0.3332	0.1384	0.089*
H7BC	1.0160	0.3758	0.2058	0.089*

	U11	U22	U33	U12	U13	U23
S1A	0.02471 (18)	0.03529 (19)	0.0583 (3)	0.00757 (13)	0.01261 (15)	0.01667 (17)
O1A	0.0498 (8)	0.0687 (9)	0.0636 (9)	0.0117 (7)	0.0238 (7)	0.0079 (7)
O2A	0.0291 (6)	0.0482 (7)	0.0888 (10)	0.0116 (5)	0.0074 (6)	0.0351 (7)
O3A	0.0338 (6)	0.0503 (7)	0.0794 (10)	−0.0034 (5)	0.0040 (6)	0.0332 (7)
O4A	0.0313 (6)	0.0516 (7)	0.0890 (10)	0.0153 (5)	0.0114 (6)	0.0311 (7)
N1A	0.0264 (6)	0.0368 (6)	0.0450 (7)	0.0026 (5)	0.0036 (5)	0.0143 (5)
N2A	0.0255 (6)	0.0385 (6)	0.0472 (7)	0.0077 (5)	0.0063 (5)	0.0156 (6)
C1A	0.0226 (6)	0.0364 (7)	0.0410 (8)	0.0041 (5)	0.0052 (5)	0.0126 (6)
C2A	0.0265 (7)	0.0440 (8)	0.0473 (9)	0.0093 (6)	0.0055 (6)	0.0159 (7)
C3A	0.0235 (7)	0.0518 (9)	0.0575 (10)	0.0048 (6)	0.0060 (6)	0.0216 (8)
C4A	0.0283 (7)	0.0419 (8)	0.0433 (8)	0.0003 (6)	0.0034 (6)	0.0167 (6)
C5A	0.0500 (11)	0.0536 (11)	0.0890 (16)	0.0007 (9)	0.0077 (10)	0.0411 (11)
C6A	0.0476 (11)	0.0511 (11)	0.1001 (18)	0.0169 (9)	0.0138 (11)	0.0339 (11)
C7A	0.0319 (8)	0.0385 (8)	0.0761 (13)	0.0027 (6)	0.0102 (8)	0.0249 (8)
S1B	0.0485 (2)	0.0379 (2)	0.0431 (2)	0.01011 (16)	0.01501 (17)	0.01859 (16)
O1B	0.0583 (9)	0.0610 (9)	0.0768 (10)	−0.0036 (7)	0.0250 (8)	0.0258 (8)
O2B	0.0830 (12)	0.0751 (10)	0.0444 (7)	0.0300 (9)	0.0083 (7)	0.0269 (7)
O3B	0.1028 (14)	0.0552 (8)	0.0543 (8)	0.0157 (8)	0.0304 (8)	0.0283 (7)
O4B	0.0800 (11)	0.0481 (8)	0.0605 (9)	0.0220 (7)	0.0250 (8)	0.0102 (7)
N1B	0.0480 (8)	0.0403 (7)	0.0440 (8)	0.0111 (6)	0.0096 (6)	0.0132 (6)
N2B	0.0465 (8)	0.0401 (7)	0.0396 (7)	0.0060 (6)	0.0089 (6)	0.0160 (6)
C1B	0.0382 (8)	0.0395 (8)	0.0376 (8)	0.0067 (6)	0.0064 (6)	0.0134 (6)
C2B	0.0506 (10)	0.0433 (9)	0.0442 (9)	0.0100 (7)	0.0103 (7)	0.0084 (7)
C3B	0.0775 (15)	0.0518 (11)	0.0430 (10)	0.0119 (10)	0.0243 (9)	0.0126 (8)
C4B	0.0593 (11)	0.0450 (9)	0.0394 (9)	0.0040 (8)	0.0115 (8)	0.0151 (7)
C5B	0.0955 (19)	0.0489 (11)	0.0579 (13)	0.0094 (11)	0.0111 (12)	0.0255 (10)
C6B	0.104 (2)	0.0477 (11)	0.0687 (14)	0.0285 (12)	0.0197 (13)	0.0182 (10)
C7B	0.0803 (15)	0.0423 (10)	0.0653 (13)	0.0231 (9)	0.0347 (11)	0.0206 (9)

S1A—O1A	1.4334 (16)	S1B—O1B	1.4234 (16)
S1A—O2A	1.4356 (14)	S1B—O2B	1.4260 (16)
S1A—C7A	1.7429 (18)	S1B—C7B	1.751 (2)
S1A—C1A	1.8059 (15)	S1B—C1B	1.8018 (17)
O3A—C4A	1.338 (2)	O3B—C4B	1.333 (2)
O3A—C5A	1.436 (3)	O3B—C5B	1.441 (3)
O4A—C2A	1.342 (2)	O4B—C2B	1.342 (2)
O4A—C6A	1.443 (2)	O4B—C6B	1.442 (3)
N1A—C1A	1.322 (2)	N1B—C1B	1.320 (2)
N1A—C4A	1.339 (2)	N1B—C2B	1.339 (2)
N2A—C1A	1.321 (2)	N2B—C1B	1.317 (2)
N2A—C2A	1.334 (2)	N2B—C4B	1.340 (2)
C2A—C3A	1.386 (2)	C2B—C3B	1.375 (3)
C3A—C4A	1.382 (2)	C3B—C4B	1.381 (3)
C3A—H3AA	0.93	C3B—H3BA	0.93
C5A—H5AA	0.96	C5B—H5BA	0.96
C5A—H5AB	0.96	C5B—H5BB	0.96
C5A—H5AC	0.96	C5B—H5BC	0.96
C6A—H6AA	0.96	C6B—H6BA	0.96
C6A—H6AB	0.96	C6B—H6BB	0.96
C6A—H6AC	0.96	C6B—H6BC	0.96
C7A—H7AA	0.96	C7B—H7BA	0.96
C7A—H7AB	0.96	C7B—H7BB	0.96
C7A—H7AC	0.96	C7B—H7BC	0.96
O1A—S1A—O2A	117.87 (10)	O1B—S1B—O2B	117.30 (11)
O1A—S1A—C7A	109.37 (10)	O1B—S1B—C7B	110.02 (12)
O2A—S1A—C7A	109.13 (9)	O2B—S1B—C7B	109.13 (12)
O1A—S1A—C1A	107.07 (8)	O1B—S1B—C1B	107.47 (9)
O2A—S1A—C1A	108.07 (8)	O2B—S1B—C1B	107.25 (9)
C7A—S1A—C1A	104.49 (8)	C7B—S1B—C1B	104.92 (9)
C4A—O3A—C5A	118.66 (14)	C4B—O3B—C5B	118.20 (16)
C2A—O4A—C6A	117.66 (14)	C2B—O4B—C6B	117.81 (17)
C1A—N1A—C4A	113.74 (14)	C1B—N1B—C2B	113.47 (15)
C1A—N2A—C2A	113.88 (14)	C1B—N2B—C4B	113.85 (15)
N2A—C1A—N1A	130.25 (14)	N2B—C1B—N1B	130.63 (16)
N2A—C1A—S1A	115.13 (11)	N2B—C1B—S1B	115.98 (12)
N1A—C1A—S1A	114.55 (11)	N1B—C1B—S1B	113.38 (13)
N2A—C2A—O4A	119.16 (15)	N1B—C2B—O4B	119.64 (18)
N2A—C2A—C3A	123.00 (15)	N1B—C2B—C3B	122.83 (17)
O4A—C2A—C3A	117.83 (15)	O4B—C2B—C3B	117.51 (17)
C4A—C3A—C2A	116.11 (15)	C2B—C3B—C4B	116.88 (17)
C4A—C3A—H3AA	121.9	C2B—C3B—H3BA	121.6
C2A—C3A—H3AA	121.9	C4B—C3B—H3BA	121.6
O3A—C4A—N1A	119.54 (15)	O3B—C4B—N2B	119.62 (17)
O3A—C4A—C3A	117.47 (15)	O3B—C4B—C3B	118.09 (17)
N1A—C4A—C3A	122.99 (15)	N2B—C4B—C3B	122.29 (17)
O3A—C5A—H5AA	109.5	O3B—C5B—H5BA	109.5
O3A—C5A—H5AB	109.5	O3B—C5B—H5BB	109.5
H5AA—C5A—H5AB	109.5	H5BA—C5B—H5BB	109.5
O3A—C5A—H5AC	109.5	O3B—C5B—H5BC	109.5
H5AA—C5A—H5AC	109.5	H5BA—C5B—H5BC	109.5
H5AB—C5A—H5AC	109.5	H5BB—C5B—H5BC	109.5
O4A—C6A—H6AA	109.5	O4B—C6B—H6BA	109.5
O4A—C6A—H6AB	109.5	O4B—C6B—H6BB	109.5
H6AA—C6A—H6AB	109.5	H6BA—C6B—H6BB	109.5
O4A—C6A—H6AC	109.5	O4B—C6B—H6BC	109.5
H6AA—C6A—H6AC	109.5	H6BA—C6B—H6BC	109.5
H6AB—C6A—H6AC	109.5	H6BB—C6B—H6BC	109.5
S1A—C7A—H7AA	109.5	S1B—C7B—H7BA	109.5
S1A—C7A—H7AB	109.5	S1B—C7B—H7BB	109.5
H7AA—C7A—H7AB	109.5	H7BA—C7B—H7BB	109.5
S1A—C7A—H7AC	109.5	S1B—C7B—H7BC	109.5
H7AA—C7A—H7AC	109.5	H7BA—C7B—H7BC	109.5
H7AB—C7A—H7AC	109.5	H7BB—C7B—H7BC	109.5
C2A—N2A—C1A—N1A	−0.7 (3)	C4B—N2B—C1B—N1B	1.4 (3)
C2A—N2A—C1A—S1A	−177.62 (12)	C4B—N2B—C1B—S1B	−179.50 (13)
C4A—N1A—C1A—N2A	−0.6 (3)	C2B—N1B—C1B—N2B	−1.2 (3)
C4A—N1A—C1A—S1A	176.33 (12)	C2B—N1B—C1B—S1B	179.75 (13)
O1A—S1A—C1A—N2A	91.31 (14)	O1B—S1B—C1B—N2B	−110.99 (15)
O2A—S1A—C1A—N2A	−140.77 (13)	O2B—S1B—C1B—N2B	122.06 (15)
C7A—S1A—C1A—N2A	−24.64 (15)	C7B—S1B—C1B—N2B	6.09 (18)
O1A—S1A—C1A—N1A	−86.07 (14)	O1B—S1B—C1B—N1B	68.23 (16)
O2A—S1A—C1A—N1A	41.86 (14)	O2B—S1B—C1B—N1B	−58.72 (16)
C7A—S1A—C1A—N1A	157.98 (13)	C7B—S1B—C1B—N1B	−174.69 (15)
C1A—N2A—C2A—O4A	−179.19 (16)	C1B—N1B—C2B—O4B	−179.21 (18)
C1A—N2A—C2A—C3A	1.8 (2)	C1B—N1B—C2B—C3B	−0.8 (3)
C6A—O4A—C2A—N2A	3.3 (3)	C6B—O4B—C2B—N1B	−14.0 (3)
C6A—O4A—C2A—C3A	−177.70 (18)	C6B—O4B—C2B—C3B	167.5 (2)
N2A—C2A—C3A—C4A	−1.6 (3)	N1B—C2B—C3B—C4B	2.1 (3)
O4A—C2A—C3A—C4A	179.42 (16)	O4B—C2B—C3B—C4B	−179.4 (2)
C5A—O3A—C4A—N1A	−3.4 (3)	C5B—O3B—C4B—N2B	−2.2 (3)
C5A—O3A—C4A—C3A	177.06 (19)	C5B—O3B—C4B—C3B	178.3 (2)
C1A—N1A—C4A—O3A	−178.65 (15)	C1B—N2B—C4B—O3B	−179.31 (19)
C1A—N1A—C4A—C3A	0.8 (2)	C1B—N2B—C4B—C3B	0.2 (3)
C2A—C3A—C4A—O3A	179.63 (16)	C2B—C3B—C4B—O3B	177.7 (2)
C2A—C3A—C4A—N1A	0.1 (3)	C2B—C3B—C4B—N2B	−1.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3AA···O2Ai	0.93	2.42	3.336 (2)	169
C5A—H5AC···O2Bii	0.96	2.55	3.303 (3)	135
C7A—H7AA···O4Aiii	0.96	2.50	3.426 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3A—H3AA⋯O2Ai	0.93	2.42	3.336 (2)	169
C5A—H5AC⋯O2Bii	0.96	2.55	3.303 (3)	135
C7A—H7AA⋯O4Aiii	0.96	2.50	3.426 (2)	161

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