2-(2-p-Tolyl­benzo[g]quinolin-3-yl)ethanol

Nan Wu; Rongli Zhang; Yumei Wang; Xin Xu; Zhou Xu

doi:10.1107/S1600536811038736

. 2011 Sep 30;67(Pt 10):o2770. doi: 10.1107/S1600536811038736

2-(2-p-Tolylbenzo[g]quinolin-3-yl)ethanol

Nan Wu ^a, Rongli Zhang ^b, Yumei Wang ^a, Xin Xu ^a, Zhou Xu ^b,^*

PMCID: PMC3201341 PMID: 22064791

Abstract

In the title compound, C₂₂H₁₉NO, the pyridine ring and the adjacent naphthalene ring system are nearly coplanar, making a dihedral angle of 3.3 (1)°, while the pyridine and benzene rings are perpendicular to each other, with a dihedral angle of 89.9 (1)°. The crystal packing is stabilized by intermolecular O—H⋯N hydrogen bonds and C—H⋯π interactions.

Related literature

For the biological activity of quinoline derivatives, see: Faber et al. (1984 ▶); Johnson et al. (1989 ▶); Nesterova et al. (1995 ▶); Yamada et al. (1992 ▶).

Experimental

Crystal data

C₂₂H₁₉NO
M _r = 313.38
Triclinic,
a = 7.2044 (4) Å
b = 10.1704 (4) Å
c = 12.1194 (3) Å
α = 108.125 (3)°
β = 98.115 (4)°
γ = 99.370 (5)°
V = 815.08 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.49 × 0.21 × 0.07 mm

Data collection

Bruker APEXII area-detector diffractometer
10164 measured reflections
2879 independent reflections
2232 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.127
S = 1.03
2879 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811038736/hg5076sup1.cif

e-67-o2770-sup1.cif^{(20KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811038736/hg5076Isup2.hkl

e-67-o2770-Isup2.hkl^{(141.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811038736/hg5076Isup3.cml

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

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

Cg is the centroid of the N1,C1–C5 pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.93 (3)	1.98 (3)	2.9110 (18)	174 (2)
C21—H21A⋯Cgⁱⁱ	0.93	2.97	3.7358 (19)	140

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

Acknowledgments

We are grateful to the Special Presidential Foundation of Xuzhou Medical College (2010KJZ15) for financial support. We thank Su Hong of Zhejiang Normal University for the data collection.

supplementary crystallographic information

Comment

Quinoline derivatives possess varies of biological properties, such as psychotropic activity (Nesterova, et al., 1995), anti-allergic (Yamada et al., 1992) and anti-inflammatory activity (Faber et al., 1984 and Johnson et al., 1989). Therefore, the title compound (Fig. 1), may be used as a new precursor for obtaining bioactive molecules. Herein, we report the crystal structure of the title compound, (I).

In the crystal structure of (I), there are four aromatic rings and the pyridine ring is the new formed ring. The pyridine ring is a coplanar conformation. The pyridine ring and the adjacent naphthalene ring are nearly coplanar, with a dihedral angle of 3.3 (1)°. While the pyridine ring and the benzene ring are vertical with each other, with a dihedral angle of 89.9 (1)°. The molecules are connected by the O1—H1···N1 intermolecular hydrogen bond and C—H···π interactions (Figure 2). Besides, there is intermolecular π-π interaction between the two neighboring benzene rings (C4C5C6C7C8C13), symmetry code: (1-X, 2-Y, –Z). The two rings are parallel to each other. The centroid distance, plane-plane distance and displacement distance are 3.642, 3.499 and 1.010 Å, respectively, which strongly indicate the existence of intermolecular π-π interactions.

Experimental

The title compound, (I), was prepared by the reaction of 4-methylbenzaldehyde (0.240 g, 2.0 mmol), naphthalen-2-amine (0.286 g, 2.0 mmol) and I₂ (0.051 g, 0.2 mmol) in THF (10 ml) at reflux for 40 h (yield 86%, mp. 486–487 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a THF solution.