1-(6-Methyl-4-phenyl-2-sulfanyl-idene-1,2,3,4-tetrahydro-pyrimidin-5-yl)ethanone.

In the title compound, C(13)H(14)N(2)OS, the heterocyclic ring adopts a flattened boat conformation with the plane through the four coplanar atoms making a dihedral angle of 86.90 (13)° with the phenyl ring, which adopts an axial orientation. The thionyl, acetyl and methyl groups all have equatorial orientations. Inter-molecular N-H⋯O, N-H⋯S and C-H⋯O hydrogen bonds are found in the crystal structure.

Related literature

For chemical and biological applications of dihydro­pyrimidinone derivatives, see: Chitra et al. (2010 ▶). For their applications and for related structures, see: Anuradha et al. (2008 ▶, 2009a ▶,b ▶,c ▶).

Experimental

Crystal data

C13H14N2OS

M = 246.33

Monoclinic,

a = 7.8849 (10) Å

b = 7.2054 (5) Å

c = 21.555 (3) Å

β = 94.401 (12)°

V = 1221.0 (2) Å3

Z = 4

Cu Kα radiation

μ = 2.23 mm−1

T = 295 K

0.44 × 0.31 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.307, T max = 1.000

4776 measured reflections

2531 independent reflections

2226 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.236

S = 1.22

2531 reflections

164 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031296/hg2697sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031296/hg2697Isup2.hkl

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

C13H14N2OS	F(000) = 520
Mr = 246.33	Dx = 1.340 Mg m−3
Monoclinic, P21/c	Melting point: 523.5 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54184 Å
a = 7.8849 (10) Å	Cell parameters from 3041 reflections
b = 7.2054 (5) Å	θ = 5.6–77.1°
c = 21.555 (3) Å	µ = 2.23 mm−1
β = 94.401 (12)°	T = 295 K
V = 1221.0 (2) Å3	Prism, colourless
Z = 4	0.44 × 0.31 × 0.16 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2531 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2226 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 10.5081 pixels mm-1	θmax = 77.3°, θmin = 5.6°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −5→9
Tmin = 0.307, Tmax = 1.000	l = −24→27
4776 measured reflections

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.236	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	w = 1/[σ2(Fo2) + (0.0912P)2 + 1.9142P] where P = (Fo2 + 2Fc2)/3
2531 reflections	(Δ/σ)max = 0.001
164 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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
S2	0.49206 (14)	−0.24803 (15)	0.06167 (5)	0.0540 (4)
O15	0.7124 (6)	0.5124 (5)	0.21330 (16)	0.0771 (13)
N1	0.6473 (5)	−0.1160 (5)	0.16583 (16)	0.0512 (11)
N3	0.5890 (4)	0.0977 (5)	0.08897 (16)	0.0456 (10)
C2	0.5819 (5)	−0.0771 (5)	0.10664 (18)	0.0444 (11)
C4	0.6849 (5)	0.2449 (5)	0.12284 (18)	0.0441 (11)
C5	0.7078 (5)	0.1972 (5)	0.19220 (17)	0.0432 (11)
C6	0.6954 (5)	0.0179 (6)	0.21040 (18)	0.0461 (11)
C15	0.7438 (6)	0.3575 (6)	0.23320 (19)	0.0516 (14)
C16	0.8242 (9)	0.3391 (8)	0.2982 (2)	0.080 (2)
C41	0.8574 (5)	0.2795 (5)	0.09762 (17)	0.0444 (11)
C42	0.9599 (6)	0.1317 (7)	0.0816 (2)	0.0585 (16)
C43	1.1194 (6)	0.1664 (8)	0.0619 (2)	0.0673 (17)
C44	1.1803 (6)	0.3452 (9)	0.0582 (2)	0.0661 (16)
C45	1.0782 (6)	0.4909 (8)	0.0726 (2)	0.0617 (16)
C46	0.9178 (6)	0.4592 (7)	0.0921 (2)	0.0548 (12)
C61	0.7244 (7)	−0.0627 (6)	0.27457 (19)	0.0603 (14)
H1	0.642 (7)	−0.225 (8)	0.173 (2)	0.061 (15)*
H3	0.565 (5)	0.118 (6)	0.049 (2)	0.047 (11)*
H4	0.61861	0.35972	0.11825	0.0528*
H16A	0.86487	0.45818	0.31279	0.1193*
H16B	0.91778	0.25375	0.29855	0.1193*
H16C	0.74161	0.29367	0.32496	0.1193*
H42	0.92086	0.01038	0.08427	0.0701*
H43	1.18682	0.06759	0.05095	0.0807*
H44	1.28923	0.36677	0.04607	0.0796*
H45	1.11727	0.61201	0.06913	0.0739*
H46	0.84985	0.55915	0.10164	0.0657*
H61A	0.84360	−0.05933	0.28748	0.0904*
H61B	0.68524	−0.18890	0.27422	0.0904*
H61C	0.66278	0.00853	0.30303	0.0904*

	U11	U22	U33	U12	U13	U23
S2	0.0612 (7)	0.0456 (6)	0.0530 (6)	−0.0106 (5)	−0.0089 (4)	−0.0029 (4)
O15	0.128 (3)	0.0362 (17)	0.065 (2)	0.0011 (19)	−0.007 (2)	−0.0031 (14)
N1	0.070 (2)	0.0316 (17)	0.0496 (18)	−0.0030 (16)	−0.0112 (15)	0.0024 (14)
N3	0.0482 (17)	0.0417 (18)	0.0448 (17)	−0.0042 (14)	−0.0101 (13)	0.0047 (14)
C2	0.0420 (18)	0.041 (2)	0.049 (2)	−0.0012 (15)	−0.0037 (15)	−0.0004 (16)
C4	0.049 (2)	0.0365 (19)	0.0455 (19)	−0.0013 (15)	−0.0050 (15)	0.0027 (15)
C5	0.0472 (19)	0.0370 (19)	0.0447 (19)	0.0005 (15)	−0.0002 (15)	0.0012 (15)
C6	0.053 (2)	0.041 (2)	0.0433 (19)	−0.0006 (17)	−0.0027 (15)	0.0009 (16)
C15	0.069 (3)	0.036 (2)	0.050 (2)	−0.0061 (18)	0.0050 (18)	−0.0008 (16)
C16	0.123 (5)	0.055 (3)	0.058 (3)	−0.021 (3)	−0.015 (3)	−0.006 (2)
C41	0.0477 (19)	0.045 (2)	0.0390 (17)	0.0012 (16)	−0.0063 (14)	0.0027 (15)
C42	0.062 (3)	0.050 (2)	0.063 (3)	0.004 (2)	0.001 (2)	0.005 (2)
C43	0.055 (3)	0.075 (3)	0.072 (3)	0.013 (2)	0.005 (2)	−0.001 (3)
C44	0.048 (2)	0.093 (4)	0.057 (2)	−0.008 (2)	0.0027 (19)	0.005 (3)
C45	0.061 (3)	0.068 (3)	0.055 (2)	−0.014 (2)	−0.002 (2)	0.003 (2)
C46	0.060 (2)	0.052 (2)	0.052 (2)	−0.006 (2)	0.0009 (18)	0.0023 (18)
C61	0.087 (3)	0.044 (2)	0.048 (2)	−0.005 (2)	−0.007 (2)	0.0057 (18)

S2—C2	1.689 (4)	C42—C43	1.381 (7)
O15—C15	1.214 (6)	C43—C44	1.379 (8)
N1—C2	1.368 (5)	C44—C45	1.373 (8)
N1—C6	1.394 (5)	C45—C46	1.382 (7)
N3—C2	1.318 (5)	C4—H4	0.9800
N3—C4	1.465 (5)	C16—H16A	0.9600
N1—H1	0.80 (6)	C16—H16B	0.9600
N3—H3	0.88 (4)	C16—H16C	0.9600
C4—C41	1.524 (6)	C42—H42	0.9300
C4—C5	1.531 (5)	C43—H43	0.9300
C5—C6	1.356 (6)	C44—H44	0.9300
C5—C15	1.469 (6)	C45—H45	0.9300
C6—C61	1.501 (6)	C46—H46	0.9300
C15—C16	1.499 (6)	C61—H61A	0.9600
C41—C46	1.388 (6)	C61—H61B	0.9600
C41—C42	1.396 (6)	C61—H61C	0.9600
S2···N3i	3.436 (4)	C16···H61C	2.7100
S2···H45ii	3.1400	C16···H61A	2.8900
S2···H16Ciii	3.1900	C42···H16Aix	2.8600
S2···H3i	2.57 (4)	C43···H16Aix	3.0800
S2···H44iv	3.1200	C45···H61Aviii	3.0500
O15···N1v	2.898 (5)	C46···H61Aviii	3.0900
O15···C41	3.283 (5)	C61···H16B	2.7700
O15···C46	3.201 (6)	C61···H16C	2.7900
O15···C61v	3.333 (6)	H1···O15vi	2.14 (6)
O15···H1v	2.14 (6)	H1···H61B	2.2000
O15···H4	2.3900	H3···S2i	2.57 (4)
O15···H46	2.7400	H4···O15	2.3900
O15···H61Bv	2.5400	H4···H46	2.3700
N1···O15vi	2.898 (5)	H16A···C42viii	2.8600
N3···S2i	3.436 (4)	H16A···C43viii	3.0800
N3···H42	2.7000	H16B···C6	3.0100
C2···C42	3.418 (6)	H16B···C61	2.7700
C15···C46	3.509 (6)	H16B···H61A	2.3400
C16···C61	3.033 (7)	H16C···C61	2.7900
C41···O15	3.283 (5)	H16C···H61C	2.1900
C42···C2	3.418 (6)	H16C···S2x	3.1900
C44···C46vii	3.563 (6)	H42···N3	2.7000
C44···C45vii	3.552 (7)	H42···C2	2.8200
C45···C46vii	3.571 (6)	H44···S2iv	3.1200
C45···C61viii	3.555 (6)	H45···S2xi	3.1400
C45···C44vii	3.552 (7)	H46···O15	2.7400
C45···C45vii	3.277 (6)	H46···H4	2.3700
C46···C15	3.509 (6)	H61A···C16	2.8900
C46···O15	3.201 (6)	H61A···H16B	2.3400
C46···C45vii	3.571 (6)	H61A···C45ix	3.0500
C46···C44vii	3.563 (6)	H61A···C46ix	3.0900
C61···C45ix	3.555 (6)	H61B···O15vi	2.5400
C61···C16	3.033 (7)	H61B···H1	2.2000
C61···O15vi	3.333 (6)	H61C···C15	3.0200
C2···H42	2.8200	H61C···C16	2.7100
C6···H16B	3.0100	H61C···H16C	2.1900
C15···H61C	3.0200
C2—N1—C6	124.4 (3)	C44—C45—C46	120.6 (5)
C2—N3—C4	125.4 (3)	C41—C46—C45	120.6 (5)
C2—N1—H1	111 (3)	N3—C4—H4	108.00
C6—N1—H1	124 (3)	C5—C4—H4	108.00
C2—N3—H3	116 (3)	C41—C4—H4	108.00
C4—N3—H3	116 (3)	C15—C16—H16A	109.00
S2—C2—N1	119.8 (3)	C15—C16—H16B	109.00
S2—C2—N3	123.8 (3)	C15—C16—H16C	110.00
N1—C2—N3	116.4 (3)	H16A—C16—H16B	109.00
N3—C4—C5	110.0 (3)	H16A—C16—H16C	109.00
C5—C4—C41	110.1 (3)	H16B—C16—H16C	109.00
N3—C4—C41	112.4 (3)	C41—C42—H42	120.00
C4—C5—C6	119.4 (3)	C43—C42—H42	120.00
C4—C5—C15	114.5 (3)	C42—C43—H43	119.00
C6—C5—C15	126.2 (4)	C44—C43—H43	119.00
C5—C6—C61	128.7 (4)	C43—C44—H44	120.00
N1—C6—C5	118.8 (4)	C45—C44—H44	120.00
N1—C6—C61	112.4 (4)	C44—C45—H45	120.00
O15—C15—C16	118.1 (4)	C46—C45—H45	120.00
C5—C15—C16	122.8 (4)	C41—C46—H46	120.00
O15—C15—C5	119.0 (4)	C45—C46—H46	120.00
C4—C41—C42	120.9 (3)	C6—C61—H61A	110.00
C4—C41—C46	120.3 (3)	C6—C61—H61B	109.00
C42—C41—C46	118.8 (4)	C6—C61—H61C	109.00
C41—C42—C43	119.7 (5)	H61A—C61—H61B	109.00
C42—C43—C44	121.1 (5)	H61A—C61—H61C	109.00
C43—C44—C45	119.2 (5)	H61B—C61—H61C	109.00
C6—N1—C2—S2	−167.7 (3)	C4—C5—C6—N1	−5.6 (6)
C6—N1—C2—N3	10.2 (6)	C4—C5—C6—C61	175.5 (4)
C2—N1—C6—C5	−12.3 (6)	C15—C5—C6—N1	175.0 (4)
C2—N1—C6—C61	166.8 (4)	C15—C5—C6—C61	−3.9 (7)
C4—N3—C2—S2	−171.4 (3)	C4—C5—C15—O15	17.8 (6)
C4—N3—C2—N1	10.9 (6)	C4—C5—C15—C16	−159.8 (5)
C2—N3—C4—C5	−25.7 (5)	C6—C5—C15—O15	−162.8 (5)
C2—N3—C4—C41	97.4 (4)	C6—C5—C15—C16	19.6 (7)
N3—C4—C5—C6	22.0 (5)	C4—C41—C42—C43	−176.7 (4)
N3—C4—C5—C15	−158.6 (3)	C46—C41—C42—C43	1.3 (6)
C41—C4—C5—C6	−102.5 (4)	C4—C41—C46—C45	176.3 (4)
C41—C4—C5—C15	77.0 (4)	C42—C41—C46—C45	−1.6 (6)
N3—C4—C41—C42	−42.5 (5)	C41—C42—C43—C44	0.5 (7)
N3—C4—C41—C46	139.6 (4)	C42—C43—C44—C45	−2.0 (7)
C5—C4—C41—C42	80.5 (4)	C43—C44—C45—C46	1.6 (7)
C5—C4—C41—C46	−97.4 (4)	C44—C45—C46—C41	0.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O15vi	0.80 (6)	2.14 (6)	2.898 (5)	158 (5)
N3—H3···S2i	0.88 (4)	2.57 (4)	3.436 (4)	168 (4)
C61—H61B···O15vi	0.96	2.54	3.333 (6)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O15i	0.80 (6)	2.14 (6)	2.898 (5)	158 (5)
N3—H3⋯S2ii	0.88 (4)	2.57 (4)	3.436 (4)	168 (4)
C61—H61B⋯O15i	0.96	2.54	3.333 (6)	140

Symmetry codes: (i) ; (ii) .