1-[4-(4-Fluoro­phen­yl)-6-methyl-2-sulfanyl­idene-1,2,3,4-tetra­hydro­pyrimidin-5-yl]ethanone

Anuradha, N.; Thiruvalluvar, A.; Chitra, S.; Devanathan, D.; Butcher, R.J.

doi:10.1107/S1600536812033727

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2625

doi:10.1107/S1600536812033727

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1-[4-(4-Fluorophenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl]ethanone

N. Anuradha,^a A. Thiruvalluvar,^a ^* S. Chitra,^b D. Devanathan ^c and R. J. Butcher ^d

^aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, ^bDepartment of Chemistry, K.S.R. College of Engineering, K.S.R. Kalvi Nagar, Tiruchengode 637 215, Tamilnadu, India, ^cDepartment of Chemistry, Government Arts College, C. Mutlur 608 102, Chidambaram, Tamilnadu, India, and ^dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA.
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

(Received 24 July 2012; accepted 26 July 2012; online 1 August 2012)

In the title molecule, C₁₃H₁₃FN₂OS, the heterocyclic ring adopts a slightly distorted flattened boat conformation, and the plane through the four coplanar atoms makes a dihedral angle of 87.45 (14)° with the benzene ring. The thione, acetyl and methyl groups lie on the opposite side of the heterocyclic mean plane to the fluorophenyl group, which has an axial orientation. N—H⋯O, N—H⋯S, C—H⋯F and C—H⋯O intermolecular hydrogen bonds and a weak C—H⋯π interaction involving the benzene ring are found in the crystal structure.

Related literature

For chemical and biological applications of dihydropyrimidine derivatives and for the closely related crystal structure of the chloro derivative, see: Anuradha et al. (2009 ).

Experimental

Crystal data

C₁₃H₁₃FN₂OS
M_r = 264.32
Triclinic, $[P \overline 1]$
a = 7.1775 (11) Å
b = 8.1099 (13) Å
c = 12.490 (2) Å
α = 103.529 (15)°
β = 91.933 (14)°
γ = 106.971 (14)°
V = 672.0 (2) Å³
Z = 2
Cu Kα radiation
μ = 2.17 mm⁻¹
T = 123 K
0.59 × 0.36 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2012 ) T_min = 0.515, T_max = 0.891
3949 measured reflections
2629 independent reflections
2109 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.233
S = 1.12
2629 reflections
173 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C41–C46 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O15ⁱ	0.82 (5)	2.10 (5)	2.867 (5)	156 (5)
N3—H3⋯S2ⁱⁱ	0.85 (6)	2.50 (6)	3.350 (4)	174 (6)
C16—H16A⋯F4ⁱⁱⁱ	0.98	2.50	3.358 (6)	146
C61—H61A⋯F4ⁱⁱⁱ	0.98	2.47	3.319 (6)	145
C61—H61B⋯O15ⁱ	0.98	2.54	3.383 (5)	144
C16—H16C⋯Cg2^iv	0.98	2.92	3.633 (5)	130
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z; (iv) x, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: DIRDIF2008 (Beurskens et al., 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812033727/wn2486sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812033727/wn2486Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812033727/wn2486Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812033727/wn2486Isup4.cml

checkCIF report

Comment top

As part of our investigations of dihydropyrimidine derivatives (Anuradha et al., 2009) to compare their chemical and biological activities, we have undertaken the X-ray cryatal structure analysis of the title compound.

In the title molecule, C₁₃H₁₃FN₂OS (Fig.1), the heterocyclic ring adopts a slightly distorted flattened boat conformation, and the plane through the four coplanar atoms (C2,N3,C5 and C6) makes a dihedral angle of 87.45 (14)° with the benzene ring. The thione, acetyl and methyl groups have equatorial orientations and the fluorophenyl group has an axial orientation. N1—H1···O15, N3—H3···S2, C16—H16A···F4, and C61—H61B···O15 intermolecular hydrogen bonds and a weak C16—H16C···π interaction involving the benzene (C41—C46) ring are found in the crystal structure (Fig.2, Table 1).

Related literature top

For chemical and biological applications of dihydropyrimidine derivatives and for the closely related crystal structure of the chloro derivative, see: Anuradha et al. (2009).

Experimental top

A solution of acetylacetone (1.0012 g, 0.01 mol), 4-fluorobenzaldehyde (1.25 g, 0.01 mol) and thiourea (1.14 g, 0.015 mol) was heated under reflux in the presence of calcium fluoride (0.07 g, 0.001 mol) for 2 h (monitored by TLC). After completion of the reaction, the reaction mixture was cooled to room temperature and poured into crushed ice. The solid product was filtered under suction and purified by recrystallization from hot methanol to give the product in the pure form. Yield 1.92 g (96%).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: DIRDIF2008 (Beurskens et al., 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The packing of the title compound, viewed along the b axis. Dashed lines indicate hydrogen bonds. H atoms not involved in hydrogen bonding have been omitted.

1-[4-(4-Fluorophenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin- 5-yl]ethanone top

Crystal data top

C₁₃H₁₃FN₂OS	Z = 2
M_r = 264.32	F(000) = 276
Triclinic, P1	D_x = 1.306 Mg m⁻³
Hall symbol: -P 1	Melting point: 509 K
a = 7.1775 (11) Å	Cu Kα radiation, λ = 1.54184 Å
b = 8.1099 (13) Å	Cell parameters from 1186 reflections
c = 12.490 (2) Å	θ = 3.7–75.9°
α = 103.529 (15)°	µ = 2.17 mm⁻¹
β = 91.933 (14)°	T = 123 K
γ = 106.971 (14)°	Plate, colourless
V = 672.0 (2) Å³	0.59 × 0.36 × 0.06 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2629 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2109 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 10.5081 pixels mm^-1	θ_max = 76.1°, θ_min = 3.7°
ω scans	h = −7→8
Absorption correction: analytical (CrysAlis PRO; Agilent, 2012)	k = −8→10
T_min = 0.515, T_max = 0.891	l = −15→11
3949 measured reflections

Refinement top

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.233	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.1003P)² + 1.2879P] where P = (F_o² + 2F_c²)/3
2629 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₃H₁₃FN₂OS	γ = 106.971 (14)°
M_r = 264.32	V = 672.0 (2) Å³
Triclinic, P1	Z = 2
a = 7.1775 (11) Å	Cu Kα radiation
b = 8.1099 (13) Å	µ = 2.17 mm⁻¹
c = 12.490 (2) Å	T = 123 K
α = 103.529 (15)°	0.59 × 0.36 × 0.06 mm
β = 91.933 (14)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2629 independent reflections
Absorption correction: analytical (CrysAlis PRO; Agilent, 2012)	2109 reflections with I > 2σ(I)
T_min = 0.515, T_max = 0.891	R_int = 0.055
3949 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	0 restraints
wR(F²) = 0.233	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.82 e Å⁻³
2629 reflections	Δρ_min = −0.37 e Å⁻³
173 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S2	0.18125 (14)	0.34721 (13)	0.46715 (10)	0.0405 (3)
F4	0.7221 (6)	0.3280 (5)	−0.0587 (3)	0.0829 (16)
O15	0.7912 (4)	−0.1016 (4)	0.3039 (3)	0.0520 (12)
N1	0.2057 (5)	0.0276 (4)	0.3682 (3)	0.0387 (10)
N3	0.4983 (5)	0.2512 (4)	0.4147 (3)	0.0349 (10)
C2	0.3046 (5)	0.2035 (5)	0.4140 (3)	0.0351 (11)
C4	0.6032 (5)	0.1414 (5)	0.3474 (3)	0.0344 (11)
C5	0.4912 (5)	−0.0550 (5)	0.3312 (3)	0.0346 (11)
C6	0.2961 (6)	−0.1043 (5)	0.3369 (3)	0.0352 (11)
C15	0.6152 (6)	−0.1729 (5)	0.3037 (4)	0.0394 (14)
C16	0.5357 (6)	−0.3717 (6)	0.2740 (4)	0.0455 (14)
C41	0.6337 (6)	0.1890 (5)	0.2361 (4)	0.0380 (11)
C42	0.4755 (7)	0.1672 (6)	0.1611 (4)	0.0450 (14)
C43	0.5034 (8)	0.2138 (7)	0.0611 (4)	0.0521 (17)
C44	0.6923 (9)	0.2814 (7)	0.0386 (4)	0.0581 (17)
C45	0.8513 (8)	0.3036 (7)	0.1095 (5)	0.0604 (17)
C46	0.8225 (7)	0.2573 (6)	0.2092 (4)	0.0473 (14)
C61	0.1533 (5)	−0.2885 (5)	0.3148 (4)	0.0403 (13)
H1	0.087 (7)	0.005 (6)	0.370 (4)	0.036 (12)*
H3	0.572 (8)	0.356 (8)	0.446 (4)	0.051 (14)*
H4	0.73478	0.16638	0.38822	0.0414*
H16A	0.45343	−0.41343	0.20285	0.0679*
H16B	0.45700	−0.40981	0.33158	0.0679*
H16C	0.64443	−0.42238	0.26819	0.0679*
H42	0.34597	0.11967	0.17837	0.0543*
H43	0.39509	0.19929	0.00998	0.0629*
H45	0.98007	0.35005	0.09089	0.0727*
H46	0.93223	0.27237	0.25940	0.0573*
H61A	0.15509	−0.35405	0.23847	0.0604*
H61B	0.02124	−0.28040	0.32542	0.0604*
H61C	0.19019	−0.35119	0.36620	0.0604*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S2	0.0293 (5)	0.0314 (5)	0.0635 (7)	0.0129 (4)	0.0089 (4)	0.0121 (4)
F4	0.093 (3)	0.086 (3)	0.062 (2)	0.003 (2)	0.0100 (18)	0.0354 (18)
O15	0.0259 (14)	0.0370 (16)	0.099 (3)	0.0146 (12)	0.0106 (15)	0.0218 (16)
N1	0.0226 (16)	0.0336 (17)	0.061 (2)	0.0104 (13)	0.0064 (14)	0.0118 (15)
N3	0.0276 (16)	0.0267 (16)	0.052 (2)	0.0093 (13)	0.0063 (14)	0.0114 (14)
C2	0.0295 (18)	0.0285 (18)	0.051 (2)	0.0105 (15)	0.0064 (16)	0.0149 (16)
C4	0.0245 (17)	0.0282 (18)	0.053 (2)	0.0101 (14)	0.0051 (15)	0.0127 (16)
C5	0.0275 (18)	0.0242 (17)	0.054 (2)	0.0083 (14)	0.0037 (15)	0.0133 (15)
C6	0.0305 (18)	0.0291 (18)	0.050 (2)	0.0115 (15)	0.0048 (15)	0.0148 (16)
C15	0.0275 (19)	0.040 (2)	0.059 (3)	0.0162 (16)	0.0079 (17)	0.0208 (18)
C16	0.033 (2)	0.038 (2)	0.072 (3)	0.0183 (17)	0.0082 (19)	0.017 (2)
C41	0.037 (2)	0.0273 (18)	0.054 (2)	0.0138 (15)	0.0089 (17)	0.0129 (16)
C42	0.039 (2)	0.043 (2)	0.056 (3)	0.0142 (18)	0.0075 (19)	0.0161 (19)
C43	0.056 (3)	0.049 (3)	0.053 (3)	0.017 (2)	0.000 (2)	0.016 (2)
C44	0.073 (3)	0.051 (3)	0.047 (3)	0.010 (2)	0.011 (2)	0.017 (2)
C45	0.055 (3)	0.059 (3)	0.059 (3)	0.001 (2)	0.015 (2)	0.019 (2)
C46	0.037 (2)	0.046 (2)	0.057 (3)	0.0072 (18)	0.0087 (19)	0.016 (2)
C61	0.0263 (18)	0.0289 (19)	0.067 (3)	0.0078 (15)	0.0098 (17)	0.0148 (18)

Geometric parameters (Å, º) top

S2—C2	1.692 (4)	C41—C42	1.390 (7)
F4—C44	1.360 (6)	C42—C43	1.392 (7)
O15—C15	1.226 (5)	C43—C44	1.372 (9)
N1—C2	1.366 (5)	C44—C45	1.363 (8)
N1—C6	1.395 (5)	C45—C46	1.388 (8)
N3—C2	1.329 (5)	C4—H4	1.0000
N3—C4	1.466 (5)	C16—H16A	0.9800
N1—H1	0.82 (5)	C16—H16B	0.9800
N3—H3	0.85 (6)	C16—H16C	0.9800
C4—C41	1.534 (6)	C42—H42	0.9500
C4—C5	1.522 (6)	C43—H43	0.9500
C5—C6	1.349 (6)	C45—H45	0.9500
C5—C15	1.479 (6)	C46—H46	0.9500
C6—C61	1.501 (6)	C61—H61A	0.9800
C15—C16	1.494 (6)	C61—H61B	0.9800
C41—C46	1.391 (7)	C61—H61C	0.9800

C2—N1—C6	124.1 (4)	C43—C44—C45	122.8 (5)
C2—N3—C4	124.0 (3)	F4—C44—C45	118.6 (6)
C2—N1—H1	113 (3)	C44—C45—C46	119.1 (5)
C6—N1—H1	123 (3)	C41—C46—C45	120.3 (5)
C2—N3—H3	123 (4)	N3—C4—H4	108.00
C4—N3—H3	113 (4)	C5—C4—H4	108.00
S2—C2—N3	123.5 (3)	C41—C4—H4	108.00
N1—C2—N3	116.3 (3)	C15—C16—H16A	110.00
S2—C2—N1	120.3 (3)	C15—C16—H16B	109.00
N3—C4—C5	109.7 (3)	C15—C16—H16C	109.00
N3—C4—C41	110.6 (3)	H16A—C16—H16B	109.00
C5—C4—C41	111.5 (3)	H16A—C16—H16C	109.00
C4—C5—C15	113.3 (3)	H16B—C16—H16C	109.00
C6—C5—C15	127.3 (4)	C41—C42—H42	119.00
C4—C5—C6	119.3 (3)	C43—C42—H42	119.00
N1—C6—C5	118.9 (4)	C42—C43—H43	121.00
N1—C6—C61	112.2 (4)	C44—C43—H43	121.00
C5—C6—C61	128.9 (4)	C44—C45—H45	120.00
C5—C15—C16	123.3 (4)	C46—C45—H45	120.00
O15—C15—C5	117.4 (4)	C41—C46—H46	120.00
O15—C15—C16	119.3 (4)	C45—C46—H46	120.00
C4—C41—C46	120.0 (4)	C6—C61—H61A	109.00
C42—C41—C46	118.8 (4)	C6—C61—H61B	109.00
C4—C41—C42	121.2 (4)	C6—C61—H61C	109.00
C41—C42—C43	121.2 (5)	H61A—C61—H61B	109.00
C42—C43—C44	117.9 (5)	H61A—C61—H61C	110.00
F4—C44—C43	118.6 (5)	H61B—C61—H61C	109.00

C6—N1—C2—S2	−170.5 (3)	C4—C5—C6—C61	174.5 (4)
C6—N1—C2—N3	8.8 (6)	C15—C5—C6—N1	177.7 (4)
C2—N1—C6—C5	−13.1 (6)	C15—C5—C6—C61	−1.6 (7)
C2—N1—C6—C61	166.4 (4)	C4—C5—C15—O15	4.4 (6)
C4—N3—C2—S2	−165.1 (3)	C4—C5—C15—C16	−174.3 (4)
C4—N3—C2—N1	15.6 (5)	C6—C5—C15—O15	−179.3 (4)
C2—N3—C4—C5	−31.5 (5)	C6—C5—C15—C16	1.9 (7)
C2—N3—C4—C41	91.8 (4)	C4—C41—C42—C43	178.7 (4)
N3—C4—C5—C6	25.6 (5)	C46—C41—C42—C43	−0.6 (7)
N3—C4—C5—C15	−157.8 (3)	C4—C41—C46—C45	−178.9 (4)
C41—C4—C5—C6	−97.2 (4)	C42—C41—C46—C45	0.4 (7)
C41—C4—C5—C15	79.4 (4)	C41—C42—C43—C44	0.3 (8)
N3—C4—C41—C42	−61.6 (5)	C42—C43—C44—F4	−179.9 (5)
N3—C4—C41—C46	117.7 (4)	C42—C43—C44—C45	0.2 (8)
C5—C4—C41—C42	60.6 (5)	F4—C44—C45—C46	179.7 (5)
C5—C4—C41—C46	−120.1 (4)	C43—C44—C45—C46	−0.4 (9)
C4—C5—C6—N1	−6.2 (5)	C44—C45—C46—C41	0.1 (8)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C41–C46 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O15ⁱ	0.82 (5)	2.10 (5)	2.867 (5)	156 (5)
N3—H3···S2ⁱⁱ	0.85 (6)	2.50 (6)	3.350 (4)	174 (6)
C16—H16A···F4ⁱⁱⁱ	0.98	2.50	3.358 (6)	146
C61—H61A···F4ⁱⁱⁱ	0.98	2.47	3.319 (6)	145
C61—H61B···O15ⁱ	0.98	2.54	3.383 (5)	144
C16—H16C···Cg2^iv	0.98	2.92	3.633 (5)	130

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃FN₂OS
M_r	264.32
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	7.1775 (11), 8.1099 (13), 12.490 (2)
α, β, γ (°)	103.529 (15), 91.933 (14), 106.971 (14)
V (Å³)	672.0 (2)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.17
Crystal size (mm)	0.59 × 0.36 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Analytical (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.515, 0.891
No. of measured, independent and observed [I > 2σ(I)] reflections	3949, 2629, 2109
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.233, 1.12
No. of reflections	2629
No. of parameters	173
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.37

Computer programs: CrysAlis PRO (Agilent, 2012), DIRDIF2008 (Beurskens et al., 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C41–C46 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O15ⁱ	0.82 (5)	2.10 (5)	2.867 (5)	156 (5)
N3—H3···S2ⁱⁱ	0.85 (6)	2.50 (6)	3.350 (4)	174 (6)
C16—H16A···F4ⁱⁱⁱ	0.98	2.50	3.358 (6)	146
C61—H61A···F4ⁱⁱⁱ	0.98	2.47	3.319 (6)	145
C61—H61B···O15ⁱ	0.98	2.54	3.383 (5)	144
C16—H16C···Cg2^iv	0.98	2.92	3.633 (5)	130

Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z; (iv) x, y−1, z.

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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Beurskens, P. T., Beurskens, G., de Gelder, R., García-Granda, S., Gould, R. O. & Smits, J. M. M. (2008). The DIRDIF2008 Program System. Crystallography Laboratory, University of Nijmegen, The Netherlands. Google Scholar
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Volume 68| Part 9| September 2012| Page o2625

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[4-(4-Fluoro­phen­yl)-6-methyl-2-sulfanyl­­idene-1,2,3,4-tetra­hydro­pyrimidin-5-yl]ethanone

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Experimental

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organic compounds

1-[4-(4-Fluorophenyl)-6-methyl-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-5-yl]ethanone