4-Methyl-2-[(E)-phen­yl(1,2,3,4-tetra­hydro-1-naphthyl­imino)meth­yl]phenol

Guang-You Zhang; Ting Yang; Bao-Wang Xu; Di-Juan Chen; Wan-Hui Wang

doi:10.1107/S1600536808030316

. 2008 Sep 24;64(Pt 10):o2007. doi: 10.1107/S1600536808030316

4-Methyl-2-[(E)-phenyl(1,2,3,4-tetrahydro-1-naphthylimino)methyl]phenol

Guang-You Zhang ^a, Ting Yang ^a,^*, Bao-Wang Xu ^b, Di-Juan Chen ^a, Wan-Hui Wang ^c

PMCID: PMC2959346 PMID: 21201205

Abstract

In the crystal structure of the title compound, C₂₄H₂₃NO, the phenyl ring makes dihedral angles of 81.53 (11) and 75.35 (12)°, respectively, with the methyl-substituted and the fused benzene rings. The dihedral angle between the two benzene rings is 71.10 (10)°. There is an intramolecular O—H⋯N hydrogen bond.

Related literature

For related structures, see: Elmali & Eleman (1998 ▶); Elmali et al. (1998 ▶). For general background, see: Bernaldi et al. (1996 ▶); Cavell et al. (2002 ▶); Desimani et al. (1995 ▶); Jacobsen et al. (1997 ▶); Kureshy et al. (1996 ▶); Nakayama et al. (2004 ▶); Takenaka et al. (2002 ▶); Varlamov et al. (2003 ▶).

Experimental

Crystal data

C₂₄H₂₃NO
M _r = 341.43
Triclinic,
a = 10.121 (3) Å
b = 10.370 (2) Å
c = 10.482 (2) Å
α = 95.181 (3)°
β = 112.830 (3)°
γ = 106.243 (4)°
V = 948.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 (2) K
0.41 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
5027 measured reflections
3467 independent reflections
2220 reflections with I > 2σ(I)
R _int = 0.015

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.128
S = 1.02
3467 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536808030316/is2336sup1.cif

e-64-o2007-sup1.cif^{(21KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030316/is2336Isup2.hkl

e-64-o2007-Isup2.hkl^{(170KB, 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
O1—H1⋯N1	0.82	1.81	2.541 (2)	147

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Acknowledgments

The authors are grateful to the Natural Science Foundation of Shandong Province China (grant No. G0231) and the Foundation of the Education Ministry of China for Returned Students (grant No. G0220) for financial support. The X-ray data were collected at Shandong Normal University, China.

supplementary crystallographic information

Comment

The synthesis of Schiff bases with a variety of functionalities is an important subject of research because this class of compounds are easily synthesized and have been widely used as ligands in the formation of almost all metal ions and asymmetric reactions (Elmali & Eleman, 1998; Elmali et al., 1998; Cavell et al., 2002; Nakayama et al., 2004; Varlamov et al., 2003; Takenaka et al., 2002; Desimani et al., 1995; Bernaldi et al., 1996; Kureshy et al., 1996; Jacobsen et al., 1997).

In this paper, we report the molecular structure of 4-methyl-2-[(E)-phenyl(1,2,3,4-tetrahydronaphthalen-1-ylimino)methyl]\ phenol, (I), which was initially prepared to test its catalytic activity. The Schiff base was prepared by conventional condensation of 1,2,3,4-tetrahydronaphthalen-1-amine with (2-hydroxy-5-methylphenyl)(phenyl)methanone in methanol.

There is an intramolecular O1—H1···N1 hydrogen bond (Table 1). Phenol atom O1 acts as a hydrogen-bond donor to atom N1, with O1··· N1= 2.541 (2) Å, which indicates a comparatively strong intramolecular hydrogen bond. This distance is significantly shorter than the sum (3.07 Å) of the van der Waals radii for N and O atoms. The O1—H1···N1 hydrogen bond in (I) completes a six-membered ring (C11/C18/C24/O1/H1/N1), which increases the stability of this compound. However, no aromatic π-π stacking interactions are present in the structure of (I).

The C12—C17 and C18—C24 aromatic rings are approximately vertical, the dihedral angle between their planes being 81.53 (11)°; the dihedral angle between the planes of the C4—C9 and C12—C17 aromatic rings is 75.35 (12)°, while that between the C4—C9 and C19—C24 planes is 71.1 (10)°.

Experimental

1,2,3,4-Tetrahydronaphthalen-1-amine (0.9 mmol) and (2-hydroxy-5-methylphenyl)(phenyl)methanone (0.9 mmol) were dissolved in methanol (10 ml) and reacted at room temperature for 48 h. After removal of the solvent, the yellow solid was obtained. Single crystals suitable for X-ray diffraction were grown by slow evaporation from an ethanol solution at room temperature.