2-[(E)-1-(4-Meth­oxy­phen­yl)pent-1-en-3-yl­idene]malononitrile

Lian-Mei Chen; Tai-Ran Kang

doi:10.1107/S1600536810045381

. 2010 Nov 13;66(Pt 12):o3148. doi: 10.1107/S1600536810045381

2-[(E)-1-(4-Methoxyphenyl)pent-1-en-3-ylidene]malononitrile

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

PMCID: PMC3011700 PMID: 21589447

Abstract

In the title compound, C₁₅H₁₄N₂O, the molecule skeleton displays an approximately planar structure except for the ethyl group [maximum deviation = 0.042 (1) Å]. The methoxyphenyl ring and butanylidenemalononitrile groups are located on opposite sides of the C=C bond, showing an E configuration. Weak intermolecular C—H⋯N hydrogen bonding is present in the crystal structure.

Related literature

For the use of malononitrile-containing compounds as building blocks in synthesis, see: Liu et al. (2002 ▶); Sepiol & Milart (1985 ▶); Zhang et al. (2003 ▶). For a related structure, see: Kang & Chen (2009 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O
M _r = 238.28
Monoclinic,
a = 12.3371 (3) Å
b = 8.8832 (2) Å
c = 12.8554 (3) Å
β = 108.050 (2)°
V = 1339.53 (5) Å³
Z = 4
Cu Kα radiation
μ = 0.60 mm⁻¹
T = 291 K
0.42 × 0.40 × 0.36 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.787, T _max = 0.813
9020 measured reflections
2456 independent reflections
2266 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.112
S = 1.05
2456 reflections
165 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.14 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/S1600536810045381/xu5082sup1.cif

e-66-o3148-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045381/xu5082Isup2.hkl

e-66-o3148-Isup2.hkl^{(120.7KB, 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
C2—H2⋯N1ⁱ	0.93	2.62	3.5285 (19)	167 (1)

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

The chemistry of ylidene malononitrile have been studied extensively, from the ring closure reactions, the comounds containing newly formed five or six-membered rings, such as indans (Zhang et al.2003), naphthalenes (Liu, et al.2002), benzenes (Sepiol et al.1985) were obtained. Some crystal structures involving ylidene malononitrile groups have been published, including a recent report from our labratory (Kang et al., 2009). As a part of our interest in the synthsis of some complex ring systems, we investigated the title compound (I), which is a diene reagent in Diels-Alder reaction. We report herein the crystal structure of the title compound.

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The phenyl ring with two double bond and triple bond is co-planar. The crystal packing is stabilized by C—H···N hydrogen bonding (Table 1).

Experimental

2-(Butan-2-ylidene)malononitrile (0.24 g 2 mmol) and 4-methoxy -benzaldehyde (0.272 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 343 K. Then the solution was cooled to room temperature, and was filtered to obtain a yellow 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.