4-Benz­yloxy-3-methoxy­benzonitrile

Muhammad Hanif; Muhammad Rafiq; Muhammad Saleem; Ghulam Qadeer; Wai-Yeung Wong

doi:10.1107/S1600536809005613

. 2009 Feb 21;65(Pt 3):o572. doi: 10.1107/S1600536809005613

4-Benzyloxy-3-methoxybenzonitrile

Muhammad Hanif ^a, Muhammad Rafiq ^a, Muhammad Saleem ^b, Ghulam Qadeer ^a,^*, Wai-Yeung Wong ^c,^‡

PMCID: PMC2968475 PMID: 21582227

Abstract

In the molecule of the title compound, C₁₅H₁₃NO₂, the aromatic rings are oriented at a dihedral angle of 81.65 (3)°. In the crystal structure, weak intermolecular C—H⋯N hydrogen bonds link the molecules into chains along the b axis.

Related literature

For the potential application of highly conjugated molecules in nanoelectronics, see: Tour (2003 ▶) and in optoelectronics, see: Lind et al. (2004 ▶); Ornelas et al. (2005 ▶, 2008 ▶). Terminal cyano groups provide the ability to coordinate to transition metal centres such as RuCp, see: Garcia et al. (2001 ▶); Ornelas et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₃NO₂
M _r = 239.26
Monoclinic,
a = 14.9434 (12) Å
b = 9.5469 (8) Å
c = 8.8522 (7) Å
β = 102.663 (2)°
V = 1232.16 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.32 × 0.25 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.864, T _max = 0.980
7286 measured reflections
2983 independent reflections
2499 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.114
S = 1.02
2983 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2009 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005613/hk2626sup1.cif

e-65-0o572-sup1.cif^{(15.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005613/hk2626Isup2.hkl

e-65-0o572-Isup2.hkl^{(146.4KB, 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
C14—H14B⋯N1ⁱ	0.98	2.58	3.5170 (17)	160

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge the financial support of the Higher Education Commission, Islamabad, Pakistan.

supplementary crystallographic information

Comment

Schiff base compounds have attracted great attention for many years. They play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, photochromism and thermochromism. We report herein the crystal structure of the title compound.

In the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C8-C13) are, of course, planar, and they are oriented at a dihedral angle of 81.65 (3)°.

In the crystal structure, weak intermolecular C-H···N hydrogen bonds (Table 1) link the molecules into chains along the b axis (Fig. 2), in which they may be effective in the stabilization of the structure.

The preparation of highly conjugated molecules has been of great interest for their potential applications in fields such as nanoelectronics (Tour, 2003) or optoelectronics (Ornelas et al., 2005, 2008; Lind et al., 2004). Terminal cyano groups provide the ability to coordinate to transition metal centres such as RuCp (Cp = cyclopentadienyl); (Garcia et al., 2001; Ornelas et al., 2005) which should result in an increase of the physical properties such as the first molecular hyperpolarizability β, which is reported to rise with the coordination to cyclopentadienylruthenium type centres (Ornelas et al., 2005, 2008). As such the preparation of the π-conjugated title compound was intended for the preparation of dinuclear ruthenium complexes for nanoelectronic application.

Experimental

For the preparation of the title compound, 4-(benzyloxy)-3-methoxy benzenamine (2.29 g, 10 mmol) was treated with sodium nitrite (0.7 g, 10 mmol) in the presence of concentrated hydrochloric acid (10 ml) at 273-278 K. Aqueous cupreous cyanate solution (48%, 1.05 g, 10 mmol) was added into the resulting diazonnium salt (1.95 g, 8 mmol). The obtained title compound was separated and recrystallized in ethanol/THF mixture (yield; 65%, m.p. 411-412 K).