(E)-3-(4-Fluoro­phen­yl)-1-[4-(methyl­sulfan­yl)phen­yl]prop-2-en-1-one

N Anuradha; A Thiruvalluvar; M Mahalinga; R J Butcher

doi:10.1107/S1600536808032807

. 2008 Oct 15;64(Pt 11):o2118–o2119. doi: 10.1107/S1600536808032807

(E)-3-(4-Fluorophenyl)-1-[4-(methylsulfanyl)phenyl]prop-2-en-1-one

N Anuradha ^a, A Thiruvalluvar ^a,^*, M Mahalinga ^b, R J Butcher ^c

PMCID: PMC2959522 PMID: 21580981

Abstract

In the title molecule, C₁₆H₁₃FOS, the dihedral angle between the two benzene rings is 8.68 (6)°. The H atoms of the central enone group are trans and one H atom is involved in a close intramolecular C—H⋯O contact. The crystal structure is stabilized by weak C—H⋯π interactions.

Related literature

For related crystal structures, see: Moorthi et al. (2005 ▶); Sathiya Moorthi, et al. (2005 ▶); Thiruvalluvar, Subramanyam, Butcher, Adhikari & Wagle (2007 ▶); Thiruvalluvar, Subramanyam, Butcher, Adhikari & Karabasanagouda (2007 ▶); Thiruvalluvar, Subramanyam, Butcher, Karegoudar & Holla (2008 ▶); Thiruvalluvar, Subramanyam, Butcher, Karabasanagouda & Adhikari (2008 ▶). For biological activities of chalcones, see: Anto et al. (1995 ▶); Vaya et al. (1997 ▶); Mukherjee et al. (2001 ▶); Indyah et al. (2000 ▶); Chen et al. (1997 ▶); Nielsen et al. (1998 ▶); Hsin et al. (1998 ▶); Kumar et al. (2003 ▶); Prasad et al. (2005 ▶).

Experimental

Crystal data

C₁₆H₁₃FOS
M _r = 272.33
Monoclinic,
a = 29.7846 (9) Å
b = 5.7070 (3) Å
c = 7.7071 (4) Å
β = 90.781 (3)°
V = 1309.94 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 200 (2) K
0.44 × 0.41 × 0.31 mm

Data collection

Oxford Diffraction R Gemini diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T _min = 0.945, T _max = 1.000 (expected range = 0.876–0.926)
11708 measured reflections
4318 independent reflections
2944 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.118
S = 1.05
4318 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; 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/S1600536808032807/lh2707sup1.cif

e-64-o2118-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032807/lh2707Isup2.hkl

e-64-o2118-Isup2.hkl^{(207.3KB, 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	2.7860 (18)	102
C12—H12⋯Cg1ⁱ	0.95	2.95	3.6803 (16)	134
C15—H15⋯Cg1ⁱⁱ	0.95	2.87	3.5494 (16)	129
C25—H25⋯Cg2ⁱⁱⁱ	0.95	2.88	3.5407 (15)	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.

Acknowledgments

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]. RJB acknowledges the NSF–MRI program for funding to purchase the X-ray CCD diffractometer.

supplementary crystallographic information

Comment

Chalcones either natural or synthetic are known to exhibit various biological activities. They have been reported to possess antioxidant (Anto et al., 1995; Vaya et al., 1997; Mukherjee et al., 2001; Indyah et al., 2000), antimalarial (Chen et al., 1997), antileishmanial(Nielsen et al., 1998), antiinflammatory(Hsin et al., 1998), antitumor(Kumar et al., 2003) and antibacterial activity(Prasad et al., 2005). The presence of a reactive unsaturated keto function in chalcones is found to be responsible for their antimicrobial activity, which may be altered depending on the type and position of substituent on the aromatic rings.

The title compound (Fig. 1) has been analysed as part of our crystallographic studies on chalcones (Thiruvalluvar, Subramanyam, Butcher, Adhikari & Wagle, 2007; Thiruvalluvar, Subramanyam, Butcher, Adhikari & Karabasanagouda, 2007; Thiruvalluvar, Subramanyam, Butcher, Karegoudar & Holla, 2008; Thiruvalluvar, Subramanyam, Butcher, Karabasanagouda & Adhikari, 2008). The dihedral angle between the two benzene rings is 8.68 (6)°. In similar structures, such as 1-(4-aminophenyl)-3-(3-bromophenyl)-prop-2-en-1-one (Sathiya Moorthi et al., 2005), 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. The H atoms of the central enone group are trans and one H atom is involved in a close intramolecular C-H···O contact. The crystal structure is stabilized by weak C12—H12···π, C15—H15···π and C25—H25···π interactions (Table 1).

Experimental

A mixture of 4-acetylthioanisole(16.6 g, 0.1 mol) and 4-fluorobenzaldehyde(12.4 g, 0.1 mol) was stirred in ethanol (30 ml) and then an aqueous solution of KOH (40%, 15 ml) added to it. The mixture was kept overnight at room temperature and then it was poured into crushed ice and acidified with HCl. The solid separated was filtered and crystallized from ethanol. Yield obtained was 85%(23.1 g).