2-(3-Nitro­phen­yl)-4-oxo-4-phenyl­butane­nitrile

Jingya Yang; Hongyan Zhou; Zheng Li

doi:10.1107/S1600536811021052

. 2011 Jun 11;67(Pt 7):o1610. doi: 10.1107/S1600536811021052

2-(3-Nitrophenyl)-4-oxo-4-phenylbutanenitrile

Jingya Yang ^a,^*, Hongyan Zhou ^b, Zheng Li ^a

PMCID: PMC3151887 PMID: 21837018

Abstract

The structure of the title compound, C₁₆H₁₂N₂O₃, contains two aromatic rings bridged by a C₃ chain. The dihedral angle between the rings is 67.6 (1)°. No classical hydrogen bonds are not found in the crystal structure.

Related literature

For the synthesis of the title compound, see: Yang et al. (2009 ▶); Yang, Shen & Chen (2010 ▶). For a related structure, see: Yang, Wu & Chen (2010 ▶). For nitrile-containing pharmaceuticals, see: Fleming et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₂N₂O₃
M _r = 280.28
Orthorhombic,
a = 10.105 (9) Å
b = 8.485 (8) Å
c = 31.37 (3) Å
V = 2690 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.28 × 0.25 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.973, T _max = 0.977
11482 measured reflections
2470 independent reflections
1541 reflections with I > 2σ(I)
R _int = 0.064

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.122
S = 1.03
2470 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811021052/bh2356sup1.cif

e-67-o1610-sup1.cif^{(21.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811021052/bh2356Isup2.hkl

e-67-o1610-Isup2.hkl^{(121.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811021052/bh2356Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811021052/bh2356Isup4.cml

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (grant No. 20772096) for financial support and Dr Yong-Liang Shao from the Center of Testing and Analysis, Lanzhou University, for the structure determination.

supplementary crystallographic information

Comment

Nitriles are important synthetic intermediates in organic synthesis, because of their easy preparations and versatile transformations (e.g. Yang, Wu & Chen, 2010). Furthermore, nitriles usually exhibit important biological and pharmacological activity. For example, many nitrile-containing pharmaceuticals are widely used in clinical treatments (Fleming et al., 2010).

Here we report on the crystal structure of the title compound, C₁₆H₁₂N₂O₃ (Fig. 1). In the structure, two aromatic rings are planar (the mean deviation from plane of the benzene ring carrying C1 is 0.0025 Å and the corresponding value of the phenyl ring carrying C10 is 0.0043 Å), but they make a large dihedral angle of 67.6 (1)°, which may be caused by the carbon chain of the bridging section that can rotate freely. From the packing diagram (Fig. 2), it can be seen that the molecules of the title compound, which display a similar V-shaped conformation, are interlayed along the a axis to form a crab-like motif and these crab-like motifs are repeatedly arranged to generate the final crystal structure.

Experimental

After Cs₂CO₃ (0.5 mg, 0.0015 mmol), (E)-3-(3-nitrophenyl)-1-phenylprop-2-en-1-one (76.0 mg, 0.3 mmol), and dioxane (0.5 ml) were charged into a dry Schlenk tube equipped with cold finger under argon, Me₃SiCN (57 ml, 0.45 mmol) and H₂O (22 ml, 1.2 mmol) were added. The reaction mixture was refluxed until the reaction was complete (monitored by TLC). Then, H₂O (2 ml) was added at r.t. and the resulting mixture was extracted with EtOAc (5 ml). The extract was washed with H₂O (2 ml), brine (3 ml), dried (Na₂SO₄), and concentrated. The crude product was purified by flash column chromatography on silica gel (PE–EtOAc, 10:1) to afford pure title compound as a yellowish solid (75.7 mg, 90% yield), as previously reported (Yang et al., 2009; Yang, Shen & Chen, 2010). Colorless single crystals of the title compound suitable for X-ray structure determination were obtained by vapour diffusion of petroleum ether into its ethyl acetate solution at room temperature.