2-(4-Meth­oxy­phen­yl)-4-oxo-4-phenyl­butane­nitrile

Alaa A-M Abdel-Aziz; Adel S El-Azab; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812006290

. 2012 Feb 17;68(Pt 3):o737. doi: 10.1107/S1600536812006290

2-(4-Methoxyphenyl)-4-oxo-4-phenylbutanenitrile

Alaa A-M Abdel-Aziz ^a,^b,^‡, Adel S El-Azab ^a,^c, Seik Weng Ng ^d,^e, Edward R T Tiekink ^d,^*

PMCID: PMC3295506 PMID: 22412617

Abstract

The title molecule, C₁₇H₁₅NO₂, is twisted, the dihedral angle between the terminal benzene rings being 63.30 (6)°. In the crystal, C—H⋯O and C—H⋯N interactions lead to supramolecular layers in the ab plane. These are connected along the c axis via C—H⋯π interactions.

Related literature

For background to the synthetic applications of 2,4-diaryl-4-oxo-butanenitriles, see: Coudert et al. (1990 ▶), 1988 ▶); Iida et al. (2007 ▶). For the preparation of the title compound, see: Coudert et al. (1990 ▶). For the structure of the unsubstituted parent compound, see: Abdel-Aziz et al. (2012 ▶).

Experimental

Crystal data

C₁₇H₁₅NO₂
M _r = 265.30
Orthorhombic,
a = 9.5730 (2) Å
b = 8.7748 (2) Å
c = 32.0620 (7) Å
V = 2693.25 (10) Å³
Z = 8
Cu Kα radiation
μ = 0.69 mm⁻¹
T = 100 K
0.30 × 0.30 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.651, T _max = 1.000
6569 measured reflections
2764 independent reflections
2410 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.101
S = 1.02
2764 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006290/xu5470sup1.cif

e-68-0o737-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006290/xu5470Isup2.hkl

e-68-0o737-Isup2.hkl^{(135.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812006290/xu5470Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8b⋯O1ⁱ	0.99	2.44	3.3102 (16)	147
C15—H15⋯N1ⁱⁱ	0.95	2.62	3.4250 (17)	143
C4—H4⋯Cgⁱⁱⁱ	0.95	2.82	3.5787 (14)	138
C17—H17c⋯Cg^iv	0.98	2.89	3.6754 (15)	138

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

Acknowledgments

This work was supported by the Research Center of Pharmacy, King Saud University, Riyadh, Saudi Arabia. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research Scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

An important class of difunctional intermediates for both the synthesis of biologically active heterocycles, such as pyridazine derivatives, and as a source ketone (Coudert et al., 1990; Coudert et al., 1988; Iida et al., 2007) are the 2,4-diaryl-4-oxo-butanenitriles. Herein, the crystal structure of a 2,4-diaryl-4-oxo-butanenitrile derivative, 4-(4-methoxyphenyl)-4-oxo-2-phenylbutanenitrile (I), is described. The structure of the parent compound is known (Abdel-Aziz et al., 2012).

In (I), Fig. 1, the terminal benzene rings form a dihedral angle of 63.30 (6)° indicating a considerable twist in the molecule. The benzyl group is twisted out of the plane of the benzene ring to which it is connected [the C2—C1—C7—C8 torsion angle is -8.58 (17)°] and in addition there is a twist around the C8—C9 bond [the C7—C8—C9—C11 torsion angle is 173.19 (10)°]. The methoxy group is co-planar with the benzene ring to which it is connected [the C17—O2—C14—C13 torsion angle is 3.03 (17)°].

In the crystal packing, molecules are linked by C—H···O and C—H···N interactions into supramolecular layers in the ab plane, Fig. 2 and Table 1. Layers are connected along the c axis via C—H···π interactions involving the (C11–C16) ring, Fig. 3 and Table 1.

Experimental

Acetone cyanohydrin (0.045 mol) and 10% aqueous sodium carbonate (0.0015 mol and 1.5 ml water) were added to solution of 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (0.015 mol) in ethanol (50 ml). The mixture was heated at reflux temperature for 4 h. After cooling, the product which separated out was filtered off and recrystallized from methanol solution.