(E)-1-[4-(Methyl­sulfan­yl)phen­yl]-3-phenyl­prop-2-en-1-one

A Thiruvalluvar; M Subramanyam; R J Butcher; T Karabasanagouda; A V Adhikari

doi:10.1107/S1600536808017200

. 2008 Jun 13;64(Pt 7):o1263. doi: 10.1107/S1600536808017200

(E)-1-[4-(Methylsulfanyl)phenyl]-3-phenylprop-2-en-1-one

A Thiruvalluvar ^a,^*, M Subramanyam ^a, R J Butcher ^b, T Karabasanagouda ^c, A V Adhikari ^c

PMCID: PMC2961704 PMID: 21202897

Abstract

In the title molecule, C₁₆H₁₄OS, the dihedral angle between the phenyl and benzene rings is 3.81 (15)°. The H atoms of the central enone group are trans. The propenone unit makes dihedral angles of 11.73 (18) and 11.62 (17)° with the benzene and phenyl rings, respectively. The crystal structure is stabilized by weak C—H⋯O and C—H⋯π interactions.

Related literature

For related crystal structures, see Sathiya Moorthi et al. (2005 ▶); Moorthi et al. (2005 ▶); Thiruvalluvar et al. (2007a ▶,b ▶).

Experimental

Crystal data

C₁₆H₁₄OS
M _r = 254.34
Orthorhombic,
a = 5.6106 (4) Å
b = 7.6239 (7) Å
c = 30.477 (2) Å
V = 1303.64 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 200 (2) K
0.49 × 0.18 × 0.15 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.849, T _max = 1.000 (expected range = 0.820–0.966)
8924 measured reflections
4060 independent reflections
3180 reflections with I > 2σ(I)
R _int = 0.069

Refinement

R[F ² > 2σ(F ²)] = 0.077
wR(F ²) = 0.181
S = 1.11
4060 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.38 e Å⁻³
Absolute structure: Flack (1983 ▶), 1314 Friedel pairs
Flack parameter: 0.11 (16)

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017200/wn2267sup1.cif

e-64-o1263-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017200/wn2267Isup2.hkl

e-64-o1263-Isup2.hkl^{(195KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1	0.95	2.42	2.781 (4)	102
C12—H12⋯Cg1ⁱ	0.95	2.99	3.704 (3)	133
C15—H15⋯Cg1ⁱⁱ	0.95	2.89	3.488 (3)	122
C25—H25⋯Cg2ⁱⁱⁱ	0.95	2.90	3.562 (3)	127

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) . Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively.

Acknowledgments

RJB acknowledges the NSF–MRI program for funding to purchase the X-ray CCD diffractometer. AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007].

supplementary crystallographic information

Comment

The title compound (Fig. 1) has been analysed as part of our crystallographic studies on chalcones (Thiruvalluvar et al. 2007a,b). The dihedral angle between the phenyl and benzene rings is 3.81 (15)°; the two rings are essentially coplanar. The H atoms of the central enone group are trans. The propenone unit makes dihedral angles of 11.73 (18)° and 11.62 (17)° with the benzene and phenyl rings, respectively.

The crystal structure is stabilized by a weak C3—H3···O1 intramolecular interaction. Furthermore, C12—H12···π, C15—H15···π and C25—H25···π interactions are also found. In similar structures, such as 1-(4-aminophenyl)-3-(3-bromophenyl)-prop-2-en-1-one (Sathiya Moorthi, et al. 2005) and 1-(4-bromophenyl)-3-(3-hydroxy phenyl)prop-2-en-1-one (Moorthi, et al. 2005), the dihedral angles between the two rings are 9.6 (1)° and 10.2 (2)°, respectively.

Experimental

Benzaldehyde (2.12 g, 0.02 mol) in ethanol (22 ml) was mixed with 4'-(methylthio)acetophenone (3.32 g, 0.02 mol) in 40 ml ethanol and the mixture was treated with 10 ml of 10% sodium hydroxide solution at 283 K and stirred at 303–305 K for 8 h. The precipitate obtained was filtered, washed with chilled ethanol and dried. Pale yellow rods of the title compound were grown from toluene by slow evaporation. The yield of the isolated product was 3.4 g (70%).