(2E)-3-[4-(Dimethyl­amino)­phen­yl]-1-(4-fluoro­phen­yl)prop-2-en-1-one

Jerry P Jasinski; Ray J Butcher; B P Siddaraju; B Narayana; H S Yathirajan

doi:10.1107/S1600536811000377

. 2011 Jan 8;67(Pt 2):o313–o314. doi: 10.1107/S1600536811000377

(2E)-3-[4-(Dimethylamino)phenyl]-1-(4-fluorophenyl)prop-2-en-1-one

Jerry P Jasinski ^a,^*, Ray J Butcher ^b, B P Siddaraju ^c, B Narayana ^d, H S Yathirajan ^c

PMCID: PMC3051752 PMID: 21523001

Abstract

The mean planes of the two benzene rings in the title compound, C₁₇H₁₆FNO, are twisted slightly, making a dihedral angle of 7.8 (1)°. The prop-2-en-1-one group is also twisted slightly with a C—C—C—O torsion angle of −11.6 (3)°. In the crystal, weak intermolecular C—H⋯O interactions link pairs of molecules, forming centrosymmetric dimers.

Related literature

Chalcones are precursors of all flavonoid-type natural products in biosynthesis, see: Marais et al. (2005 ▶). For their pharmacological activity, see: Di Carlo et al. (1999 ▶) and for their antimalarial activity, see: Ram et al. (2000 ▶); Troeberg et al. (2000 ▶). For the synthesis and biological activity of some fluorinated chalcone derivatives, see: Nakamura et al. (2002 ▶). For a review of anti-infective and anti-inflammatory chalcones, see: Nowakowska (2007 ▶) and for recent advances in therapeutic chalcones, see: Ni et al. (2004 ▶). For related structures, see: Butcher et al. (2006 ▶, 2007a ▶,b ▶); Harrison et al. (2006 ▶); Jasinski et al. (2009 ▶); Jing (2009 ▶); Sarojini et al. (2007 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₆FNO
M _r = 269.31
Monoclinic,
a = 12.8334 (3) Å
b = 12.3560 (2) Å
c = 9.3922 (2) Å
β = 105.965 (2)°
V = 1431.87 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.56 × 0.47 × 0.22 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T _min = 0.675, T _max = 1.000
6644 measured reflections
2929 independent reflections
2098 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.197
S = 1.10
2929 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000377/xu5139sup1.cif

e-67-0o313-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000377/xu5139Isup2.hkl

e-67-0o313-Isup2.hkl^{(143.8KB, 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
C17—H17A⋯O1ⁱ	0.96	2.56	3.525 (3)	180

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Symmetry code: (i) Inline graphic .

Acknowledgments

BN thanks Mangalore University for the use of research facilities and the UGC for financial assistance. HSY thanks UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

supplementary crystallographic information

Comment

Chalcones are known as the precursors of all flavonoid type natural products in biosynthesis (Marais et al., 2005). Chalcones, one of the major classes of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based foodstuff have been recently subjects of interest for their interesting pharmacological activities (Di Carlo et al., 1999). Many chalcones have been described for their high antimalarial activity, probably as a result of michael addition of nucleophilic species to the double bond of the enone (Troeberg et al., 2000 & Ram et al., 2000). Synthesis and biological activities of some fluorinated chalcone derivatives is published (Nakamura et al., 2002). A review of anti-infective and anti-inflammatory chalcones (Nowakowska, 2007) and recent advances in therapeutic chalcones have been reported (Ni et al., 2004). The crystal structures of few related fluoro chalcones viz., 3-(3,4-dimethoxyphenyl)-1-(4-fluorophenyl)prop-2-en-1-one (Butcher et al., 2006), (2E)-3-(4-fluorophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one (Butcher et al., 2007a), (2E)-3-(4-fluorophenyl)-1-(4-methylphenyl)prop-2-en-1-one (Butcher et al., 2007b), a second polymorph of (2E)-1-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Jasinski, et al., 2009), (E)-3-(4-fluorophenyl)-1-phenyl-2-propen-1-one (Jing, 2009), 1-(4-fluorophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (Harrison et al., 2006) and 3-(biphenyl-4-yl)-1-(4-fluorophenyl)prop-2-en-1-one (Sarojini et al., 2007) have been reported. In a continuation of our studies and in view of the importance of fluoro chalcones, we report the synthesis and crystal structure of a new chalcone, C₁₇H₁₆FNO, (I).

The mean planes of the two benzene rings in the title compound, C₁₇H₁₆FNO, are twisted slightly being separated by 7.8 (0)° (Fig. 2). The prop-2-en-1-one group is also twisted slightly with a C2—C1—C7—O1 torsion angle of -11.6 (3)°. Bond distances and angles are in normal ranges (Allen et al., 1987). A weak C—H···O intermolecular interaction (Table 1) contributes to crystal packing creating a centrosymmetric dimer (Fig. 3).

Experimental

4-Fluoroaetophenone (1.38 g, 0.01 mol) was mixed with 4-(dimethylamino)benzaldehyde (1.49 g, 0.01 mol) and dissolved in ethanol (40 ml) (Fig. 1). To this solution 10 ml of KOH (30%) was added at 273 K. The reaction mixture stirred for 4 h and poured on to crushed ice. The resulting crude solid was filtered, washed successively with dilute HCl solution and distilled water and finally recrystallized from ethanol (95%) to give the pure chalcone. Crystals suitable for X-ray diffraction studies were grown by the slow evaporation of the solution of the compound in ethyl acetate (M.P.: 383–388 K). Composition: Found (Calculated) for C₁₇H₁₆FNO; C: 75.77 (75.82%); H: 5.96 (5.99%); N: 5.16 (5.20%).