2-Eth­oxy-4-(4-methyl­phen­yl)-6-phenyl­pyridine-3-carbonitrile

Shaaban K Mohamed; Mehmet Akkurt; Antar A Abdelhamid; Kuldip Singh; Mahoud A A El-Remaily

doi:10.1107/S1600536812032163

. 2012 Jul 18;68(Pt 8):o2495–o2496. doi: 10.1107/S1600536812032163

2-Ethoxy-4-(4-methylphenyl)-6-phenylpyridine-3-carbonitrile

Shaaban K Mohamed ^a, Mehmet Akkurt ^b,^*, Antar A Abdelhamid ^a, Kuldip Singh ^c, Mahoud A A El-Remaily ^d

PMCID: PMC3414949 PMID: 22904936

Abstract

The title compound, C₂₁H₁₈N₂O, crystallized with two independent molecules (A and B) in the asymmetric unit. In molecule A, the central pyridine ring forms dihedral angles of 14.55 (13) and 39.14 (12)° with the terminal phenyl and benzene rings, respectively. The latter rings make a dihedral angle of 33.06 (13)° with each other. The corresponding values for molecule B are 26.86 (13), 41.82 (12) and 38.99 (13)°, respectively. In the crystal, the B molecules are linked via a pair of weak C—H⋯N hydrogen bonds, forming inversion dimers. In addition, C—H⋯π interactions and π–π [centroid–centroid distances = 3.5056 (16) and 3.8569 (17) Å] stacking interactions are observed.

Related literature

For the bioactivity of pyridine compounds, see: Cook et al. (2004 ▶); Upton et al. (2000 ▶); Ellefson et al. (1978 ▶). For the synthesis of bioactive molecules, see: El-Sawy et al. (2012 ▶); Soliman et al. (2012 ▶). For a similar structure, see: Patel et al. (2002 ▶).

Experimental

Crystal data

C₂₁H₁₈N₂O
M _r = 314.37
Monoclinic,
a = 14.786 (3) Å
b = 14.634 (3) Å
c = 15.399 (3) Å
β = 92.288 (4)°
V = 3329.4 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 150 K
0.35 × 0.15 × 0.11 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.986, T _max = 0.991
25600 measured reflections
6846 independent reflections
3334 reflections with I > 2σ(I)
R _int = 0.105

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.157
S = 0.81
6846 reflections
433 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032163/su2474sup1.cif

e-68-o2495-sup1.cif^{(40.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032163/su2474Isup2.hkl

e-68-o2495-Isup2.hkl^{(335KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812032163/su2474Isup3.cml

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

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

Cg2, Cg5 and Cg6 are the centroids of the C6–C11, C6A–C11A and C12A–C17A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13A—H13A⋯N2A ⁱ	0.93	2.59	3.353 (3)	139
C19—H19A⋯Cg6ⁱⁱ	0.97	2.72	3.622 (3)	155
C20—H20B⋯Cg5	0.96	2.76	3.693 (3)	163
C20A—H20E⋯Cg2	0.96	2.83	3.746 (3)	159

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

Acknowledgments

The authors are grateful to the Higher Education Ministry of Egypt in collaboration with Manchester Metropolitan University for their financial support of this project. They also thank Erciyes University and the University of Leicester for facilitating this study.

supplementary crystallographic information

Comment

Pyridine containing compounds possess a wide range of biological properties (Cook et al., 2004; Upton et al., 2000; Ellefson et al., 1978). Functionalized pyridine derivatives can act as antifungal (Cook et al., 2004), antifertility (Upton et al., 2000) and antiarrhythmic agents (Ellefson et al., 1978). We herein report on the synthesis and crystal structure of the title compound as a part of our on-going project on the synthesis of bioactive molecules (El-Sawy et al., 2012; Soliman et al., 2012).

The molecular structures of the two independent molecules (A and B) of the title compound have similar conformations (Figs. 1 & 2). In molecule A the N1/C1–C5 pyridine ring forms dihedral angles of 14.55 (13) and 39.14 (12)° with the C6–C11 phenyl and C12–C17 benzene rings, respectively. The latter rings make a dihedral angle of 33.06 (13)° with each other. The corresponding values for the B molecule are 26.86 (13), 41.82 (12) and 38.99 (13)°, respectively. The values of the bond lengths and bond angles are in the normal range and are comparable to those reported for a similar structure (Patel et al., 2002).

In the crystal, the B molecules are linked via pairs of C—H···N hydrogen bonds to form inversion dimers that stack together with the A molecules along the c axis direction (Table 1 and Fig. 3). Inter- and intra-molecular C—H···π interactions (Table 1) and π-π [Cg1···Cg4(x, y, z) = 3.5056 (16) Å and Cg2···Cg4(x, 1/2 - y, -1/2 + z) = 3.8569 (17) Å; where Cg1, Cg2 and Cg4 are the centroids of the N1/C1–C5, C6–C11 and N1A/C1A–C5A rings, respectively] interactions contribute to the stabilization of the crystal packing.

Experimental

The title compound was prepared by heating a mixture of (2E)-3-(4-methylphenyl)-1-phenylprop-2-en-1-one (222 mg, 1 mmol), propanedinitrile (66 mg, 1 mmol) and sodium methoxide (10 mg) as a catalyst in 50 ml e thanol at 350 K for 7 h. The solid product that resulted on cooling was filtered off, dried and recrystallized from acetone. Single crystals suitable for X-ray analyses were grown by slow evaporation of an acetone solution of the title compound over 24 h [M.p. 383 K].