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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o2052.
Published online 2009 July 31. doi:  10.1107/S1600536809029699
PMCID: PMC2977375

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

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 [triangle]); Bhatia et al. (1999 [triangle]); Meth-Cohn et al. (1999 [triangle]); Thijs et al. (1990 [triangle]).

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Object name is e-65-o2052-scheme1.jpg

Experimental

Crystal data

  • C15H12N2O4
  • M r = 284.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2052-efi1.jpg
  • 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
  • Δρmax = 0.12 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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.

Refinement

The H4 atom was located in a difference Fourier map and refined isotropically. The carbon-bound hydrogen atoms were placed in calculated positions with C—H = 0.93–0.98 Å, and refined using a riding model with Uiso(H) =1.2Ueq(C). Friedel pairs were merged.

Figures

Fig. 1.
The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

Crystal data

C15H12N2O4F(000) = 296
Mr = 284.27Dx = 1.421 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1633 reflections
a = 5.9800 (3) Åθ = 2.9–29.0°
b = 5.1960 (4) ŵ = 0.11 mm1
c = 21.503 (5) ÅT = 293 K
β = 96.105 (5)°Block, colorless
V = 664.35 (17) Å30.36 × 0.30 × 0.10 mm
Z = 2

Data collection

Oxford Diffraction Gemini S Ultra diffractometer821 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray SourceRint = 0.054
graphiteθmax = 26.4°, θmin = 2.9°
ω scansh = −7→7
6118 measured reflectionsk = −6→5
1515 independent reflectionsl = −26→26

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.042H atoms treated by a mixture of independent and constrained refinement
S = 1.13w = 1/[σ2(Fo2) + (0.0006P)2] where P = (Fo2 + 2Fc2)/3
1515 reflections(Δ/σ)max < 0.001
194 parametersΔρmax = 0.12 e Å3
2 restraintsΔρmin = −0.13 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O40.6579 (3)0.2311 (5)0.48448 (11)0.0686 (8)
O20.7928 (4)1.2561 (5)0.25607 (9)0.0691 (7)
N10.8102 (5)0.8270 (6)0.17913 (12)0.0573 (8)
O30.3472 (3)0.2679 (5)0.42342 (10)0.0766 (8)
N20.5421 (5)0.3314 (6)0.44030 (13)0.0566 (9)
C100.8251 (5)0.9283 (6)0.34170 (14)0.0437 (9)
C140.8515 (4)0.6302 (6)0.42748 (13)0.0459 (9)
H140.93010.56060.46320.055*
C40.7716 (6)0.6203 (7)0.13644 (14)0.0511 (10)
C150.9424 (4)0.8237 (7)0.39512 (14)0.0491 (9)
H151.08480.88610.40900.059*
O11.1883 (4)0.7951 (6)0.20507 (10)0.0919 (9)
C130.6412 (5)0.5415 (7)0.40592 (15)0.0398 (9)
C110.6126 (5)0.8330 (7)0.32131 (13)0.0524 (10)
H110.53230.90080.28560.063*
C81.0022 (6)1.1420 (7)0.24713 (14)0.0596 (10)
H81.12141.26600.24100.071*
C120.5216 (5)0.6395 (7)0.35375 (14)0.0530 (10)
H120.37940.57550.34030.064*
C90.9241 (5)1.1506 (7)0.30983 (14)0.0527 (10)
H90.99991.27860.33820.063*
C50.9264 (5)0.5501 (8)0.09757 (14)0.0604 (11)
H51.06390.63480.09960.072*
C71.0093 (7)0.9023 (7)0.20860 (15)0.0618 (11)
C60.8787 (6)0.3529 (8)0.05514 (15)0.0726 (12)
H60.98470.30640.02850.087*
C30.5675 (5)0.4925 (8)0.13414 (15)0.0646 (11)
H30.46230.53820.16110.078*
C10.6773 (6)0.2246 (7)0.05169 (15)0.0703 (12)
H10.64620.09180.02310.084*
C20.5224 (5)0.2959 (9)0.09128 (17)0.0710 (11)
H20.38500.21070.08920.085*
H40.678 (3)0.890 (6)0.1938 (12)0.087 (13)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O40.0732 (16)0.057 (2)0.0750 (16)−0.0043 (14)0.0071 (12)0.0141 (15)
O20.1047 (18)0.0473 (19)0.0558 (15)0.0221 (16)0.0106 (14)−0.0014 (16)
N10.066 (2)0.061 (3)0.0451 (18)0.019 (2)0.0055 (17)−0.004 (2)
O30.0612 (15)0.070 (2)0.0974 (17)−0.0300 (15)0.0046 (12)−0.0074 (17)
N20.062 (2)0.048 (3)0.061 (2)−0.0070 (19)0.0153 (17)−0.012 (2)
C100.054 (2)0.040 (3)0.038 (2)−0.0007 (18)0.0097 (17)−0.0077 (19)
C140.047 (2)0.045 (3)0.044 (2)−0.0014 (19)−0.0018 (16)−0.003 (2)
C40.070 (2)0.047 (3)0.036 (2)0.022 (2)0.0045 (19)0.000 (2)
C150.0508 (19)0.055 (3)0.0412 (19)−0.003 (2)0.0016 (17)−0.005 (2)
O10.0763 (16)0.104 (2)0.0930 (19)0.0260 (17)−0.0025 (14)−0.047 (2)
C130.047 (2)0.034 (3)0.040 (2)−0.0027 (17)0.0094 (17)−0.0042 (17)
C110.054 (2)0.056 (3)0.046 (2)0.012 (2)−0.0023 (17)−0.001 (2)
C80.091 (3)0.039 (3)0.050 (2)−0.005 (2)0.0143 (19)0.000 (2)
C120.046 (2)0.061 (3)0.051 (2)−0.005 (2)0.0018 (18)−0.009 (2)
C90.074 (2)0.040 (3)0.044 (2)0.003 (2)0.0054 (19)−0.007 (2)
C50.074 (2)0.065 (3)0.044 (2)0.004 (2)0.014 (2)−0.009 (2)
C70.084 (3)0.056 (3)0.046 (2)0.007 (2)0.012 (2)0.004 (2)
C60.085 (3)0.075 (4)0.058 (2)0.004 (3)0.009 (2)−0.012 (3)
C30.061 (2)0.069 (3)0.064 (3)0.015 (2)0.008 (2)0.008 (2)
C10.093 (3)0.052 (3)0.062 (3)0.012 (3)−0.008 (2)−0.004 (2)
C20.068 (3)0.065 (3)0.077 (3)−0.006 (2)−0.008 (2)0.004 (3)

Geometric parameters (Å, °)

O4—N21.230 (3)C13—C121.364 (3)
O2—C81.417 (3)C11—C121.369 (4)
O2—C91.435 (3)C11—H110.9300
N1—C71.346 (4)C8—C91.474 (4)
N1—C41.416 (4)C8—C71.499 (4)
N1—H40.940 (10)C8—H80.9800
O3—N21.229 (2)C12—H120.9300
N2—C131.477 (4)C9—H90.9800
C10—C111.391 (3)C5—C61.381 (4)
C10—C151.391 (4)C5—H50.9300
C10—C91.497 (4)C6—C11.371 (4)
C14—C151.368 (4)C6—H60.9300
C14—C131.373 (3)C3—C21.383 (5)
C14—H140.9300C3—H30.9300
C4—C51.361 (4)C1—C21.374 (4)
C4—C31.386 (4)C1—H10.9300
C15—H150.9300C2—H20.9300
O1—C71.216 (3)
C8—O2—C962.22 (18)C9—C8—H8114.1
C7—N1—C4126.9 (3)C7—C8—H8114.1
C7—N1—H4118.2 (19)C13—C12—C11119.4 (3)
C4—N1—H4113.5 (19)C13—C12—H12120.3
O3—N2—O4123.5 (3)C11—C12—H12120.3
O3—N2—C13118.0 (3)O2—C9—C858.28 (18)
O4—N2—C13118.5 (3)O2—C9—C10117.0 (3)
C11—C10—C15119.0 (3)C8—C9—C10125.1 (3)
C11—C10—C9121.5 (3)O2—C9—H9114.7
C15—C10—C9119.4 (3)C8—C9—H9114.7
C15—C14—C13118.3 (3)C10—C9—H9114.7
C15—C14—H14120.8C4—C5—C6119.9 (3)
C13—C14—H14120.8C4—C5—H5120.1
C5—C4—C3120.2 (3)C6—C5—H5120.1
C5—C4—N1121.8 (4)O1—C7—N1125.3 (4)
C3—C4—N1118.0 (3)O1—C7—C8119.5 (4)
C14—C15—C10120.9 (3)N1—C7—C8115.2 (3)
C14—C15—H15119.5C1—C6—C5121.0 (3)
C10—C15—H15119.5C1—C6—H6119.5
C12—C13—C14122.3 (3)C5—C6—H6119.5
C12—C13—N2119.0 (3)C2—C3—C4119.1 (3)
C14—C13—N2118.7 (3)C2—C3—H3120.4
C12—C11—C10120.0 (3)C4—C3—H3120.4
C12—C11—H11120.0C6—C1—C2118.8 (4)
C10—C11—H11120.0C6—C1—H1120.6
O2—C8—C959.50 (19)C2—C1—H1120.6
O2—C8—C7120.0 (3)C1—C2—C3121.0 (4)
C9—C8—C7124.1 (3)C1—C2—H2119.5
O2—C8—H8114.1C3—C2—H2119.5
C7—N1—C4—C5−32.3 (5)C7—C8—C9—C10−4.9 (6)
C7—N1—C4—C3149.1 (3)C11—C10—C9—O2−1.9 (4)
C13—C14—C15—C100.0 (4)C15—C10—C9—O2−178.1 (3)
C11—C10—C15—C14−0.1 (4)C11—C10—C9—C8−70.6 (4)
C9—C10—C15—C14176.2 (3)C15—C10—C9—C8113.2 (4)
C15—C14—C13—C120.0 (4)C3—C4—C5—C60.8 (5)
C15—C14—C13—N2179.6 (3)N1—C4—C5—C6−177.8 (3)
O3—N2—C13—C12−6.0 (4)C4—N1—C7—O1−3.5 (5)
O4—N2—C13—C12174.6 (3)C4—N1—C7—C8175.0 (3)
O3—N2—C13—C14174.4 (3)O2—C8—C7—O1−174.5 (3)
O4—N2—C13—C14−5.1 (4)C9—C8—C7—O1−103.0 (4)
C15—C10—C11—C120.1 (4)O2—C8—C7—N16.9 (4)
C9—C10—C11—C12−176.1 (3)C9—C8—C7—N178.4 (4)
C9—O2—C8—C7114.3 (4)C4—C5—C6—C1−0.4 (5)
C14—C13—C12—C110.1 (4)C5—C4—C3—C2−1.0 (5)
N2—C13—C12—C11−179.6 (3)N1—C4—C3—C2177.7 (3)
C10—C11—C12—C13−0.1 (4)C5—C6—C1—C20.1 (5)
C8—O2—C9—C10−116.3 (3)C6—C1—C2—C3−0.3 (5)
C7—C8—C9—O2−107.6 (4)C4—C3—C2—C10.7 (5)
O2—C8—C9—C10102.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.393.267 (4)158
C15—H15···O3ii0.932.533.353 (4)148

Symmetry codes: (i) x−1, y, z; (ii) x+1, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2566).

References

  • Bhatia, B., Jain, S., De, A., Bagchi, I. & Iqbal, J. (1999). Tetrahedron Lett.37, 7311–7314.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Meth-Cohn, O. & Chen, Y. (1999). Tetrahedron Lett.40, 6069–6072.
  • Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, England.
  • Righi, G., Rumboldt, G. & Bonini, C. (1996). J. Org. Chem.61, 3557–3560.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Thijs, L., Porskamp, J. J. M., van Loon, A. A. W. M., Derks, M. P. W., Feenstra, R. W., Legters, J. & Zwanenburg, B. (1990). Tetrahedron, 46, 2611–2614.

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