(E)-Ethyl 2-cyano-3-(furan-2-yl)acrylate

Rajesh G Kalkhambkar; D Gayathri; Vivek K Gupta; Rajni Kant; Yeon Tae Jeong

doi:10.1107/S1600536812016510

. 2012 Apr 21;68(Pt 5):o1482. doi: 10.1107/S1600536812016510

(E)-Ethyl 2-cyano-3-(furan-2-yl)acrylate

Rajesh G Kalkhambkar ^a, D Gayathri ^b, Vivek K Gupta ^c, Rajni Kant ^c, Yeon Tae Jeong ^d,^*

PMCID: PMC3344592 PMID: 22590354

Abstract

There are two independent molecules in the asymmetric unit of the title compound, C₁₀H₉NO₃, in both of which, all non-H atoms except for the methyl C atom lie nearly in the same plane [maximum deviations = 0.094 (3) and 0.043 (2) Å]. In the crystal, each independent molecules is linked by pairs of C—H⋯O interactions, generating inversion dimers with R ₂ ²(10) ring motifs.

Related literature

For the synthesis of related compounds, see: Yadav et al. (2004 ▶). For related structures, see: Wang & Jian (2008 ▶); Zhang et al. (2009 ▶); Ye et al. (2009 ▶); Yuvaraj et al. (2011 ▶).

Experimental

Crystal data

C₁₀H₉NO₃
M _r = 191.18
Monoclinic,
a = 4.6611 (2) Å
b = 19.8907 (9) Å
c = 20.9081 (9) Å
β = 91.988 (4)°
V = 1937.28 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T _min = 0.933, T _max = 0.990
12870 measured reflections
4568 independent reflections
2407 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.209
S = 1.04
4568 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016510/is5119sup1.cif

e-68-o1482-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016510/is5119Isup2.hkl

e-68-o1482-Isup2.hkl^{(219.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812016510/is5119Isup3.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
C5A—H5A⋯O2Aⁱ	0.93	2.40	3.242 (3)	151
C5B—H5B⋯O2Bⁱⁱ	0.93	2.46	3.320 (3)	153

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

YTJ is thankful for the support provided by the second stage of the BK-21 program. The authors thank the Director, USIC University of Jammu, Jammu Tawi, India, for the X-ray data collection.

supplementary crystallographic information

Comment

Knoevenagel condensation is an important carbon-carbon bond forming reaction in organic synthesis (Yadav et al., 2004). In continuation of our work on nitrogen and oxygen based heterocycles, we herein report the crystal structure of the title compound.

The title compound crystallizes in monoclinic system with two molecules in the asymmetric unit. Bond lengths and bond angles are comparable with the similar crystal structures solved earlier (Zhang et al., 2009; Wang & Jian, 2008; Ye et al., 2009; Yuvaraj et al., 2011). All the non-hydrogen atoms, except the methyl group, lie nearly in the same plane with a maximum out-of-plane deviation of 0.094 (3) and 0.043 (2) Å (r.m.s deviation = 0.04 and 0.024 Å), respectively, for molecules A and B. Difference in the torsion angles C7A—O3A—C8A—C9A [-167.4 (3)°] and C7B—O3B—C8B—C9B [125.3 (4)°] has been observed, indicating the flexibility of the methyl group. The crystal packing is stabilized by C—H···O intermolecular interactions generating the centrosymmetric dimer of R₂²(10) ring motif.

Experimental

A solution of furan-2-aldehyde (1 mol), ethyl cyanoacetate (1.2 mol) and piperidine (0.1 ml) in ethanol (20 ml) was stirred at room temperature for 8 h. After removal of the volatiles in vacuo, orange solid was obtained in quantitative yield. A sample for analysis was obtained by recrystallization from EtOAc as pale yellow needles: ¹H NMR (300 MHz, CDCl₃) δ p.p.m.: 1.42 (t, 3H, CH₃), 4.40 (q, 2H, CH₂), 6.61 (m, 1H, CH), 6.80 (m, 1H, CH), 7.28 (m, 1H, CH), 7.98 (s, 1H, HC=C).