3,5,6-Trimethyl-thieno[2,3-d]pyrimidin-4(3H)-one.

In the title compound, C(9)H(10)N(2)OS, the thienopyrimidine ring system is almost planar [greatest deviation from the mean plane = 0.0318 (13) Å for the S atom]. The crystal packing features C-H⋯O hydrogen bonds and π-π stacking inter-actions between inversion-related pairs of mol-ecules with a centroid-centroid distance of 3.530 (3) Å.

Related literature

For the synthesis, properties and biological activity of pyrim­idinone derivatives, see: Litvinov (2004 ▶); Al-Taisan et al. (2010 ▶). For the crystal and mol­ecular structures of related compounds, see: Tashkhodzhaev et al. (2002 ▶).

Experimental

Crystal data

C9H10N2OS

M = 194.25

Monoclinic,

a = 8.027 (3) Å

b = 10.706 (5) Å

c = 10.907 (3) Å

β = 97.333 (3)°

V = 929.7 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.77 mm−1

T = 293 K

0.42 × 0.36 × 0.28 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.324, T max = 1.000

2983 measured reflections

1588 independent reflections

1208 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.151

S = 1.05

1588 reflections

122 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035416/aa2064sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035416/aa2064Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035416/aa2064Isup3.cml

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

C9H10N2OS	F(000) = 408
Mr = 194.25	Dx = 1.388 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 185 reflections
a = 8.027 (3) Å	θ = 4.1–43.7°
b = 10.706 (5) Å	µ = 2.77 mm−1
c = 10.907 (3) Å	T = 293 K
β = 97.333 (3)°	Block, colourless
V = 929.7 (6) Å3	0.42 × 0.36 × 0.28 mm
Z = 4

Oxford Diffraction Xcalibur Ruby diffractometer	1588 independent reflections
Radiation source: fine-focus sealed tube	1208 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.2576 pixels mm-1	θmax = 67.2°, θmin = 5.6°
ω scans	h = −8→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.324, Tmax = 1.000	l = −13→11
2983 measured reflections

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.151	w = 1/[σ2(Fo2) + (0.1022P)2 + 0.0132P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1588 reflections	Δρmax = 0.27 e Å−3
122 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: 0.0070 (14)

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
C1	0.3074 (3)	0.1156 (2)	0.4761 (3)	0.0448 (7)
C2	0.4524 (4)	0.1684 (3)	0.6555 (3)	0.0559 (8)
H2	0.5198	0.2239	0.7052	0.067*
C3	0.3198 (3)	−0.0372 (3)	0.6401 (2)	0.0467 (7)
C4	0.2664 (3)	−0.0020 (2)	0.5153 (2)	0.0396 (6)
C5	0.1683 (3)	−0.0728 (2)	0.4196 (2)	0.0446 (7)
C6	0.1362 (4)	−0.0066 (3)	0.3125 (2)	0.0498 (7)
C7	0.4735 (4)	0.0352 (4)	0.8380 (3)	0.0693 (10)
H7A	0.3808	0.0084	0.8791	0.104*
H7B	0.5195	0.1109	0.8754	0.104*
H7C	0.5584	−0.0285	0.8454	0.104*
C8	0.1125 (4)	−0.2045 (3)	0.4345 (3)	0.0615 (8)
H8A	0.0263	−0.2062	0.4879	0.092*
H8B	0.2062	−0.2539	0.4699	0.092*
H8C	0.0690	−0.2379	0.3551	0.092*
C9	0.0413 (4)	−0.0454 (4)	0.1917 (3)	0.0694 (9)
H9A	−0.0690	−0.0091	0.1831	0.104*
H9B	0.0319	−0.1348	0.1890	0.104*
H9C	0.0998	−0.0173	0.1254	0.104*
N1	0.4025 (3)	0.2028 (2)	0.5443 (2)	0.0537 (6)
N2	0.4153 (3)	0.0576 (2)	0.7075 (2)	0.0505 (6)
O1	0.2922 (3)	−0.13487 (19)	0.69116 (18)	0.0595 (6)
S1	0.22443 (10)	0.14187 (7)	0.32561 (6)	0.0543 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0458 (16)	0.0418 (14)	0.0482 (15)	0.0049 (11)	0.0116 (12)	−0.0006 (11)
C2	0.0553 (19)	0.0501 (17)	0.062 (2)	0.0007 (13)	0.0055 (14)	−0.0163 (14)
C3	0.0443 (16)	0.0495 (16)	0.0468 (15)	0.0075 (12)	0.0074 (12)	−0.0022 (12)
C4	0.0368 (14)	0.0398 (14)	0.0430 (14)	0.0064 (10)	0.0081 (11)	0.0000 (10)
C5	0.0427 (16)	0.0448 (15)	0.0470 (15)	0.0027 (11)	0.0083 (12)	−0.0010 (11)
C6	0.0476 (17)	0.0553 (17)	0.0458 (15)	0.0063 (13)	0.0036 (12)	−0.0013 (12)
C7	0.073 (2)	0.088 (3)	0.0436 (17)	0.0157 (18)	−0.0037 (15)	−0.0115 (15)
C8	0.067 (2)	0.0505 (17)	0.067 (2)	−0.0105 (14)	0.0080 (16)	−0.0035 (14)
C9	0.072 (2)	0.083 (2)	0.0512 (18)	−0.0023 (18)	−0.0023 (15)	−0.0075 (16)
N1	0.0568 (15)	0.0428 (13)	0.0613 (16)	0.0001 (11)	0.0071 (12)	−0.0060 (11)
N2	0.0519 (14)	0.0564 (15)	0.0419 (13)	0.0091 (11)	0.0006 (10)	−0.0089 (10)
O1	0.0688 (15)	0.0553 (13)	0.0531 (12)	0.0013 (10)	0.0025 (10)	0.0164 (9)
S1	0.0631 (6)	0.0502 (5)	0.0493 (5)	0.0040 (3)	0.0068 (3)	0.0099 (3)

C1—N1	1.365 (4)	C6—C9	1.494 (4)
C1—C4	1.382 (4)	C6—S1	1.739 (3)
C1—S1	1.714 (3)	C7—N2	1.461 (4)
C2—N1	1.282 (4)	C7—H7A	0.9600
C2—N2	1.364 (4)	C7—H7B	0.9600
C2—H2	0.9300	C7—H7C	0.9600
C3—O1	1.218 (3)	C8—H8A	0.9600
C3—N2	1.419 (4)	C8—H8B	0.9600
C3—C4	1.424 (4)	C8—H8C	0.9600
C4—C5	1.441 (3)	C9—H9A	0.9600
C5—C6	1.362 (4)	C9—H9B	0.9600
C5—C8	1.495 (4)	C9—H9C	0.9600
N1—C1—C4	126.3 (3)	N2—C7—H7C	109.5
N1—C1—S1	122.1 (2)	H7A—C7—H7C	109.5
C4—C1—S1	111.6 (2)	H7B—C7—H7C	109.5
N1—C2—N2	125.8 (3)	C5—C8—H8A	109.5
N1—C2—H2	117.1	C5—C8—H8B	109.5
N2—C2—H2	117.1	H8A—C8—H8B	109.5
O1—C3—N2	119.6 (3)	C5—C8—H8C	109.5
O1—C3—C4	127.9 (3)	H8A—C8—H8C	109.5
N2—C3—C4	112.4 (2)	H8B—C8—H8C	109.5
C1—C4—C3	118.9 (2)	C6—C9—H9A	109.5
C1—C4—C5	112.6 (2)	C6—C9—H9B	109.5
C3—C4—C5	128.5 (2)	H9A—C9—H9B	109.5
C6—C5—C4	112.0 (2)	C6—C9—H9C	109.5
C6—C5—C8	123.8 (3)	H9A—C9—H9C	109.5
C4—C5—C8	124.2 (2)	H9B—C9—H9C	109.5
C5—C6—C9	129.1 (3)	C2—N1—C1	113.8 (3)
C5—C6—S1	112.0 (2)	C2—N2—C3	122.6 (2)
C9—C6—S1	118.9 (2)	C2—N2—C7	119.2 (3)
N2—C7—H7A	109.5	C3—N2—C7	118.2 (3)
N2—C7—H7B	109.5	C1—S1—C6	91.90 (13)
H7A—C7—H7B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.32	3.250 (4)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.32	3.250 (4)	173

Symmetry code: (i) .