2-[3-(2-Chloro­phen­yl)-5-oxo-1,5-diphenyl­pentyl­idene]malononitrile

Bai-Xiang Du; Jie Zhou; Yu-Ling Li; Xiang-Shan Wang

doi:10.1107/S1600536810050622

. 2010 Dec 11;67(Pt 1):o62. doi: 10.1107/S1600536810050622

2-[3-(2-Chlorophenyl)-5-oxo-1,5-diphenylpentylidene]malononitrile

Bai-Xiang Du ^a,^*, Jie Zhou ^a, Yu-Ling Li ^a, Xiang-Shan Wang ^a

PMCID: PMC3050168 PMID: 21522773

Abstract

In the title compound, C₂₆H₁₉ClN₂O, the 2-chlorophenyl group forms dihedral angles of 59.6 (1) and 31.9 (1)° with the phenyl rings. The two phenyl rings are inclined at a dihedral angle of 32.9 (1)° with respect to each other. In the crystal, an intermolecular C—H⋯N hydrogen bond links the molecules into a polymeric chain running along the c axis.

Related literature

For water as an attractive medium for organic reactions, see: Breslow (1991 ▶). For a related structure, see: Zhou et al. (2007 ▶).

Experimental

Crystal data

C₂₆H₁₉ClN₂O
M _r = 410.88
Orthorhombic,
a = 12.4450 (3) Å
b = 14.3866 (3) Å
c = 24.1913 (5) Å
V = 4331.24 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.50 × 0.39 × 0.29 mm

Data collection

Bruker SMART CCD area-detector diffractometer
34193 measured reflections
5019 independent reflections
2972 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.153
S = 1.04
5019 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810050622/pv2363sup1.cif

e-67-00o62-sup1.cif^{(21.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050622/pv2363Isup2.hkl

e-67-00o62-Isup2.hkl^{(245.9KB, 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
C8—H8A⋯N1ⁱ	0.97	2.62	3.502 (3)	152

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to the Natural Science Foundation (08KJD150019) and the Qing Lan Project (08QLT001) of the Jiangsu Education Committee for financial support.

supplementary crystallographic information

Comment

There has been a growing recognition that water has become an attractive medium for many organic reactions (Breslow, 1991). Recently, we have demonstrated the Michal addition reaction between 2-(1-phenylethylidene)malononitrile and 1-phenyl-3-(2-chlorophenyl)propen-1-one in water without a catalyst and synthesized the title compound which is reported in this article.

In the title compound (Fig. 1), 2-chlorophenyl group forms dihedral angles of 59.6 (1) and 31.9 (1) ° with benzene rings (C1—C6) and (C15—C20), respectively. The two benzene rings are inclined with respect to each other at a dihedral angle of 32.9 (1) °. There is an intermolecular hydrogen bond C8—H8A···N1 (Table 1) resulting in a polymeric chain along the c-axis. In addition, two intramolecular interactions further stabilize the structure (Fig. 2).

Experimental

The title compound was prepared by the reaction of 2-(1-phenylethylidene)malononitrile (0.168 g, 1.0 mmol) and 1-phenyl-3-(2-chlorophenyl)propen-1-one (0.242 g, 1.0 mmol) in water (10 ml) at reflux for 14 h (yield 82%, mp. 438–439 K). Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a dimethylformamide solution.