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

Rajni Kant; Vivek K Gupta; Kamini Kapoor; Madhukar B Deshmukh; D R Patil; P V Anbhule

doi:10.1107/S160053681204202X

. 2012 Oct 13;68(Pt 11):o3110. doi: 10.1107/S160053681204202X

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

Rajni Kant ^a,^*, Vivek K Gupta ^a, Kamini Kapoor ^a, Madhukar B Deshmukh ^b, D R Patil ^b, P V Anbhule ^b

PMCID: PMC3515216 PMID: 23284436

Abstract

In the title compound, C₁₁H₁₂FNO, the dihedral angle between the prop-2-en-1-one group and the benzene ring is 19.33 (6)°. The configuration of the keto group with respect to the olefinic double bond is s-cis. In the crystal, the molecules form dimers through aromatic π–π stacking interactions [centroid–centroid distance = 3.667 (1) Å] and are linked via C—H⋯O interactions into chains along the b axis.

Related literature

For the synthesis and pharmaceutical activity of enaminones, see: Kantevari et al. (2007 ▶); Ke et al. (2009 ▶); Omran et al. (1997 ▶); Eddington et al. (2003 ▶). For a related structure, see: Deng et al. (2010 ▶).

Experimental

Crystal data

C₁₁H₁₂FNO
M _r = 193.22
Monoclinic,
a = 13.2832 (6) Å
b = 5.8530 (2) Å
c = 14.2995 (8) Å
β = 116.086 (6)°
V = 998.49 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.824, T _max = 1.000
14183 measured reflections
1952 independent reflections
1430 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.133
S = 1.04
1952 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(19.3KB, cif)}

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681204202X/gk2520sup1.cif

e-68-o3110-sup1.cif^{(19.3KB, cif)}

Click here for additional data file.^{(94.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204202X/gk2520Isup2.hkl

e-68-o3110-Isup2.hkl^{(94.1KB, hkl)}

Click here for additional data file.^{(4.1KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681204202X/gk2520Isup3.cml

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
C6—H6B⋯O1ⁱ	0.96	2.59	3.531 (3)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. He is also thankful to the University of Jammu, Jammu, India, for financial support.

supplementary crystallographic information

Comment

(2E)-3-(Dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one is a versatile substrate used for synthesis of number of heterocyclic compounds and drug intermediates (Kantevari et al., 2007; Ke et al., 2009; Omran et al., 1997; Eddington et al., 2003).

The molecular structure of the title compound (I) is shown in Fig.1. The bond lengths and angles observed in (I) show normal values and are comparable with a related structure (Deng et al., 2010). The dihedral angle between prop-2-en-1-one group and the phenyl ring is 19.33 (6) °. Molecules in the unit cell are packed together to form one dimensional assembly along the b axis (Fig.2) through intermolecular C6—H6B···O1 interactions (Table 1). The crystal structure is further stabilized by π–π interactions between the benzene ring (C7—C12) of the molecule at (x, y, z) and the benzene ring of an inversion related molecule at (- x, - y, -z)[centroid separation = 3.667 (1) Å, interplanar spacing = 3.535 Å and centroid shift = 0.97 Å].

Experimental

In a 50 ml round bottom flask charged with 5 mmole of 4-methyl acetophenone and 5 mmole of dimethylformamide dimethyl acetal. Then 10 ml toulene was added and the reaction mixture was stirred for 3 h at 110°C. The reaction was monitored by TLC. After completion of reaction and cooling the reaction mixture was evaporated under vacuum. Finally, the product was isolated by column chromatography using ethyl acetate and n-hexane(2/8 vol.). Yield: 85%. IR(KBr): 1643, 1598, 1550,1439 cm-1. ¹H NMR (300 MHz, CDCl3): 2.93(s, 3H, N—CH3), 3.15(s, 3H, N—CH3), 5.65–5.69 (d, 1H, =CH), 7.79–7.83(d, 1H,=CH), 7.05–7.11(m, 2H, Ar—H), 7.89–7.94 (m, 2H, Ar—H).