(2Z)-2-(4-Methyl­phen­yl)-3-(2-naphth­yl)prop-2-enenitrile

Abdullah Mohamed Asiri; Mehmet Akkurt; Islam Ullah Khan; Muhammad N Arshad; Salman A Khan

doi:10.1107/S1600536809034229

. 2009 Sep 9;65(Pt 10):o2409. doi: 10.1107/S1600536809034229

(2Z)-2-(4-Methylphenyl)-3-(2-naphthyl)prop-2-enenitrile

Abdullah Mohamed Asiri ^a, Mehmet Akkurt ^b,^*, Islam Ullah Khan ^c, Muhammad N Arshad ^c, Salman A Khan ^a

PMCID: PMC2970233 PMID: 21577869

Abstract

In the title compound, C₂₀H₁₅N, the dihedral angle between the naphthalene and benzene rings is 60.30 (16)°. The crystal packing features very weak intermolecular C—H⋯π interactions.

Related literature

For background on the commercial importance and applications of styryl dyes, see: Haidekker et al. (2001 ▶); Hamer (1964 ▶); Li et al. (1998 ▶); Makoto et al. (2000a ▶,b ▶); Mousnier et al. (2004 ▶); Park et al. (2001 ▶); Pommeret et al. (1995 ▶); Spalletti (2004 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₀H₁₅N
M _r = 269.33
Orthorhombic,
a = 12.3194 (11) Å
b = 16.4796 (16) Å
c = 7.2596 (7) Å
V = 1473.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.37 × 0.28 × 0.13 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: none
16248 measured reflections
3659 independent reflections
1549 reflections with I > 2σ(I)
R _int = 0.092

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.174
S = 0.95
3659 reflections
192 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809034229/hb5070sup1.cif

e-65-o2409-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034229/hb5070Isup2.hkl

e-65-o2409-Isup2.hkl^{(175.8KB, 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
C2—H2⋯Cg1ⁱ	0.93	2.98	3.682 (4)	134
C7—H7⋯Cg2ⁱⁱ	0.93	2.93	3.695 (4)	140
C9—H9⋯Cg1ⁱⁱ	0.93	2.78	3.473 (4)	133

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Symmetry codes: (i) Inline graphic ; (ii) . Cg1 and Cg2 are the centroids of the C1–C3/C8–C10 and C3–C8 rings, respectively.

Acknowledgments

AMA acknowledges the Chemistry Department, Faculty of Science, King Abdul-Aziz University, for providing the laboratories and facilities.

supplementary crystallographic information

Comment

Styryl dyes are of commercial importance, not only because of their applications as pigment, but also due to their high technology applications, such as sensitizers formerly (Hamer, 1964), electroluminescence (Makoto et al., 2000a,b), photochromism (Spalletti, 2004), photography (Li et al., 1998), fluorescent probes (Haidekker et al., 2001), optical recording materials (Park et al., 2001), laser dyes (Pommeret et al., 1995) and in the field of medication (Mousnier et al., 2004).

The structure of the title compound (I) is shown in Fig. 1. All bond lengths (Allen et al., 1987) and bond angles in (I) may be regarded as normal. The naphthalene ring in (I) is almost planar, with the maximum deviations of -0.008 (3), 0.015 (3), -0.009 (4) and -0.008 (4) Å for atoms C1, C2, C5 and C8, respectively. The mean plane of the naphthalene ring makes a dihedral angle of 60.30 (16)° with the benzene ring of the 2-(4-methylphenyl) group.

The crystal packing is stabilized by weak intermolecular C—H···π interactions between the centroids of the two six-membered rings (C1–C3/C8–C10) and (C3–C8) of naphthalene of the adjacent molecules (Table 1). Fig. 2 shows the packing arrangement in the unit cell, as viewed down the a axis.

Experimental

A mixture of 4-methyl benzylcyanide (1.00 g, 0.0076 mol) and 2-napthaldehyde (1.18 g, 0.0076 mol) in anhydrous ethanol (15 ml), in the presence of pyridine was refluxed at 353 K for 3 h with continuous stirring. Progress of reaction was monitored by TLC. After completion of the reaction solution was cooled. The heavy precipitate thus obtained was collected by filtration and purified by recrystallization from methanol and chloroform [m.p.: 412 K, yield: 57%] to yield pale yellow prisms of (I).