3-(4-Nitro­phen­yl)-N-phenyl­oxirane-2-carboxamide

Long He

doi:10.1107/S1600536809029699

. 2009 Jul 31;65(Pt 8):o2052. doi: 10.1107/S1600536809029699

3-(4-Nitrophenyl)-N-phenyloxirane-2-carboxamide

Long He ^a,^*

PMCID: PMC2977375 PMID: 21583714

Abstract

The molecule of the title compound, C₁₅H₁₂N₂O₄, adopts a syn conformation with the terminal benzene rings located on the same sides of the central epoxide ring. The epoxide ring makes dihedral angles of 71.08 (18) and 60.83 (17)° with the two benzene rings. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For epoxide-containing compounds used as building blocks in synthesis, see: Righi et al. (1996 ▶); Bhatia et al. (1999 ▶); Meth-Cohn et al. (1999 ▶); Thijs et al. (1990 ▶).

Experimental

Crystal data

C₁₅H₁₂N₂O₄
M _r = 284.27
Monoclinic,
a = 5.9800 (3) Å
b = 5.1960 (4) Å
c = 21.503 (5) Å
β = 96.105 (5)°
V = 664.35 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.36 × 0.30 × 0.10 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: none
6118 measured reflections
1515 independent reflections
821 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.042
S = 1.13
1515 reflections
194 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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 (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029699/xu2566sup1.cif

e-65-o2052-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029699/xu2566Isup2.hkl

e-65-o2052-Isup2.hkl^{(74.7KB, 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
C3—H3⋯O1ⁱ	0.93	2.39	3.267 (4)	158
C15—H15⋯O3ⁱⁱ	0.93	2.53	3.353 (4)	148

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

Acknowledgments

The diffraction measurements were made at the Centre for Testing and Analysis, Chengdu Branch, Chinese Academy of Sciences. We acknowledge financial support from China West Normal University.

supplementary crystallographic information

Comment

Oxiranecarboxamides are the key building blocks in the synthesis of natural products such as the Taxol side chain (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). isoserine derivatives (Bhatia et al. 1999). The crystal structure of the title compound is reported here.

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The two phenyl ring is the cis conformation, the dihedral angle between the two phenyl ring is 77.34 (8)°. Epoxide ring makes dihedral angles of 71.08 (18)° and 60.83 (17)° with phenyl rings C1—C6 and C10—C15, respectively. The crystal packing is stabilized by C—H···0 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 4-nitrophenylaldehyde (0.15 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 (0.01 g) in ethanol (2 ml) and evaporating the solvent slowly at room temperature for about 3 d.