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

Long He; Hong-Mei Qin; Lian-Mei Chen

doi:10.1107/S1600536809045929

. 2009 Nov 4;65(Pt 12):o2999. doi: 10.1107/S1600536809045929

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

Long He ^a,^*, Hong-Mei Qin ^b, Lian-Mei Chen ^a

PMCID: PMC2972056 PMID: 21578739

Abstract

In the molecule of the title compound, C₁₅H₁₂BrNO₂, the two benzene rings adopt a syn configuration with respect to the epoxy ring; the dihedral angles between the epoxy ring and the two benzene rings are 59.90 (13) and 68.01 (12)°. Intermolecular N—H⋯O and C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For epoxide-containing compounds used as building blocks in synthesis, see: Flisak et al. (1993 ▶); Watanabe et al. (1998 ▶); Zhu & Espenson (1995 ▶). For related structures, see: He (2009 ▶); He & Chen (2009 ▶). graphic file with name e-65-o2999-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₂BrNO₂
M _r = 318.17
Orthorhombic,
a = 6.71700 (10) Å
b = 10.0370 (2) Å
c = 20.4287 (3) Å
V = 1377.27 (4) Å³
Z = 4
Cu Kα radiation
μ = 4.05 mm⁻¹
T = 295 K
0.40 × 0.40 × 0.36 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 ▶) T _min = 0.294, T _max = 0.324
17721 measured reflections
2701 independent reflections
2675 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.028
wR(F ²) = 0.069
S = 1.01
2701 reflections
177 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.42 e Å⁻³
Absolute structure: Flack (1983 ▶), 1104 Friedel pairs
Flack parameter: −0.008 (18)

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/S1600536809045929/xu2664sup1.cif

e-65-o2999-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045929/xu2664Isup2.hkl

e-65-o2999-Isup2.hkl^{(129.9KB, 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
N1—H1⋯O2ⁱ	0.79 (3)	2.22 (3)	2.971 (2)	161 (2)
C15—H15⋯O1ⁱⁱ	0.93	2.59	3.442 (3)	153

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

Acknowledgments

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

supplementary crystallographic information

Comment

Epoxides are important intermediates in organic synthesis. Glycidic esters and amides are particularly useful as they can be further transformed to key intermediates of several pharmaceutical products (Flisak et al. 1993; Watanabe et al. 1998). The Darzens reaction, is one of the most powerful methodologies for the synthesis of α, β-epoxy carbonyl and related compounds (Zhu & Espenson, 1995). 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. In the molecule, the two phenyl ring adopts a cis configuration about the epoxides ring. The dihedral angle between the C1—C6 and C10—C15 is 77.05 (7)°, O1/C7/C8 epoxide ring makes dihedral angles of 59.90 (13)° and 68.01 (12)° with C6 and C15 phenyl ring, respectively, which is similar to that found in a related structure (He & Chen, 2009). The crystal packing is stabilized by N—H···0 and C—H···0 hydrogen bonding (Table 1).

Experimental

2-Chloro-N-phenylacetamide (0.17 g, 1.0 mmol) and potassium hydroxide (0.112 g, 2.0 mmol) were dissolved in acetonitrile (2 ml). To the solution was added 2-bromophenylaldehyde (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. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature for 1 d.