3-(3-Cyano­phen­yl)-N-phenyl­oxirane-2-carboxamide

Tai-Ran Kang

doi:10.1107/S1600536810037475

. 2010 Sep 25;66(Pt 10):o2628. doi: 10.1107/S1600536810037475

3-(3-Cyanophenyl)-N-phenyloxirane-2-carboxamide

Tai-Ran Kang ^a,^*

PMCID: PMC2983245 PMID: 21587601

Abstract

In the title compound, C₁₆H₁₂N₂O₂, both terminal benzene rings are located at the same side of the central epoxide ring, showing a cis conformation. The epoxide ring makes dihedral angles of 76.59 (10) and 62.40 (11)° with the phenyl and cyanophenyl rings, respectively. Intermolecular N—H⋯O and weak C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the use of epoxide-containing compounds as building blocks in synthesis, see: Meth-Cohn & Chen (1999 ▶); Porter & Skidmore (2000 ▶); Righi et al. (1996 ▶); Thijs et al. (1990 ▶). For related structures, see: Chen & Kang (2009a ▶,b ▶); He (2009 ▶); He et al. (2009 ▶).

Experimental

Crystal data

C₁₆H₁₂N₂O₂
M _r = 264.28
Orthorhombic,
a = 5.459 (2) Å
b = 11.141 (7) Å
c = 21.844 (5) Å
V = 1328.6 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 291 K
0.36 × 0.32 × 0.26 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
9766 measured reflections
2078 independent reflections
1378 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.072
S = 1.00
2078 reflections
181 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037475/xu5025sup1.cif

e-66-o2628-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037475/xu5025Isup2.hkl

e-66-o2628-Isup2.hkl^{(100.1KB, 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
N1—H4⋯O1ⁱ	0.86	2.46	3.239 (3)	151 (1)
C11—H11⋯O1ⁱ	0.93	2.56	3.467 (3)	165 (1)
C12—H12⋯O2ⁱⁱ	0.93	2.55	3.302 (3)	139 (1)

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

Acknowledgments

The diffraction measurements were made at the Centre for Testing and Analysis, Sichuan University. We acknowledge financial support from China West Normal University.

supplementary crystallographic information

Comment

α, β-epoxides are key intermediates for synthesizing some natural products (Porter & Skidmore, 2000; Righi et al., 1996). Selective ring opening reactions of oxiranes also provide powerful and efficient routes to a variety of useful compounds including 2,3-epoxyketone (Meth-Cohn et al., 1999), aziridinecarboxylate (Thijs et al., 1990). Various effective systems have been developed over the years for the preparation of chiral epoxides. As a part of our interest in the synthsis of epoxides ring systems (Chen & Kang, 2009a,b; He, 2009, He et al. (2009)), we synthesis the title compound by using Darzens 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 cyanophenyl ring and N-phenylformamide units adopts a cis conformation with respect to the epoxides ring, the dihedral angle between the two phenyl ring is 84.75 (6)°. Epoxide ring makes dihedral angles of 76.59 (10)° and 62.40 (11)° with phenyl rings C1—C6 and C10—C15, respectively. The crystal packing is stabilized by C—H···O and N—H···O hydrogen bonding (Table 1).

Experimental

2-Chloro-N-phenylacetamide (0.17 g, 1.0 mmol) and sodium ethanolate (0.14 g, 2.0 mmol) were dissolved in acetonitrile (2 ml). To the solution was added 3-formylbenzonitrile (0.131 g, 1.0 mmol) at 298 K, the solution was stirred for 60 min and removal of solvent under reduced pressure, the residue was purified through column chromatography on silica gel to give compound (I). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.02 g) in ethyl acetate (2 ml) and evaporating the solvent slowly at room temperature for about 1 d.