(E)-N-Benzyl-2-cyano-3-phenyl­acryl­amide

Tai-Ran Kang; Lian-Mei Chen

doi:10.1107/S1600536810049548

. 2010 Dec 4;67(Pt 1):o8. doi: 10.1107/S1600536810049548

(E)-N-Benzyl-2-cyano-3-phenylacrylamide

Tai-Ran Kang ^a,^*, Lian-Mei Chen ^a

PMCID: PMC3050274 PMID: 21522791

Abstract

In the title compound, C₁₇H₁₄N₂O, the N-benzylformamide and phenyl groups are located on the opposite sides of the C=C bond, showing an E configuration; the terminal phenyl rings are twisted to each other at a dihedral angle of 63.61 (7)°. Intermolecular classical N—H⋯N and weak C—H⋯O hydrogen bonds occur in the crystal structure.

Related literature

For the use of malononitrile-containing compounds as building blocks in syntheses, see: Lee et al. (2002 ▶); Rajan et al. (2001 ▶); Yingyongnarongkul et al. (2006 ▶). For a related structure, see: Kang & Chen (2009 ▶).

Experimental

Crystal data

C₁₇H₁₄N₂O
M _r = 262.30
Triclinic,
a = 5.8956 (3) Å
b = 9.9224 (5) Å
c = 12.1400 (7) Å
α = 94.508 (5)°
β = 99.544 (4)°
γ = 98.895 (4)°
V = 687.95 (6) Å³
Z = 2
Cu Kα radiation
μ = 0.64 mm⁻¹
T = 291 K
0.36 × 0.35 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.803, T _max = 0.832
5416 measured reflections
2407 independent reflections
2202 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.096
S = 1.05
2407 reflections
185 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.12 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049548/xu5098sup1.cif

e-67-000o8-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049548/xu5098Isup2.hkl

e-67-000o8-Isup2.hkl^{(115.8KB, 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
N2—H4⋯N1ⁱ	0.88 (1)	2.24 (1)	3.0687 (14)	157 (1)
C3—H3⋯O1ⁱⁱ	0.93	2.36	3.2672 (16)	164

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

Acknowledgments

The authors thank the Testing Centre of the Sichuan University for the diffraction measurements and are grateful for financial support from China West Normal University (No. 412374).

supplementary crystallographic information

Comment

The phenylacrylamide derivatives have broad application for the preparation of heterocyclic ring compounds. The phenylacrylamide derivatives was studied extensively, Rajan (Rajan et al.,2001) synthesized a series of phenylacrylamide derivatives and evaluated their antioxidant properties as lipid peroxidation inhibitors. Some phenylacrylamide derivatives and analogues were synthesized and studied antibacterial activity against S. aureus (Yingyongnarongkul et al.,2006). Some phenylacrylamide derivatives were synthesized for the purpose of simplifying the structure of L-chicoric acid as new HIV-1 integrase inhibitors (Lee et al., 2002).As an extension of this research, we report the synthesis and the crystal structure of the title compound (I), namely, (E)—N-benzyl-2-cyano-3-phenylacrylamide.

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The dihedral angle between the C1—C6 and C12—C17 benzene planes is 63.62 (5)°. The crystal packing is stabilized by N—H···N an C—H···O hydrogen bonding (Table 1).

Experimental

N-Benzyl-2-cyanoacetamide (0.258 g, 2 mmol) and benzaldehyde (0.212 g, 2 mmol) were dissolved in 2-propanol (2 ml). To the solution was added piperidine (0.017 g, 0.2 mmol),the solution was stirred for 24 h at 273 K and the solution was filtered to obtain a solid. Recrystallization from hot ethanol afforded the pure compound. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation ethanol solvent.