2-(3,4-Dichloro­phen­yl)-4-phenyl­benzo[h]quinoline

Nan Wu; Zhou Xu

doi:10.1107/S1600536811040049

. 2011 Oct 5;67(Pt 11):o2850. doi: 10.1107/S1600536811040049

2-(3,4-Dichlorophenyl)-4-phenylbenzo[h]quinoline

Nan Wu ^a, Zhou Xu ^b,^*

PMCID: PMC3247588 PMID: 22219893

Abstract

In the title compound, C₂₅H₁₅Cl₂N, the benzo[h]quinoline system exhibits an approximately planar conformation with an r.m.s. deviation of 0.0202Å and a maximum deviation of 0.039 (1) Å. The aryl group at position 2 is nearly coplanar with the parent ring [dihedral angle = 6.68 (7)°] while the parent ring and the phenyl subsitituent at position 4 form a dihedral angle of 67.11 (4)°. Intermolecular C—H⋯π interactions stabilize the crystal packing.

Related literature

For the uses of metal complexes of benzo[h]quinoline as electronic materials and organic electronic devices, see: Cho et al. (2010 ▶). For the medicinal uses of benzo[h]quinoline and its complexes, see: Pantoom et al. (2011 ▶); Liu et al. (2011 ▶). For the preparation of the title compound, see: Zhang et al. (2010 ▶).

Experimental

Crystal data

C₂₅H₁₅Cl₂N
M _r = 400.28
Monoclinic,
a = 10.6066 (14) Å
b = 9.5667 (12) Å
c = 18.824 (2) Å
β = 94.264 (7)°
V = 1904.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002) ▶ T _min = 0.933, T _max = 0.959
23687 measured reflections
4523 independent reflections
3630 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.110
S = 1.07
4523 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2002) ▶; cell refinement: CrystalClear ▶; data reduction: CrystalClear ▶; 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) I, global. DOI: 10.1107/S1600536811040049/hg5101sup1.cif

e-67-o2850-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040049/hg5101Isup2.hkl

e-67-o2850-Isup2.hkl^{(221.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811040049/hg5101Isup3.cml

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

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

Cg1, Cg2 and Cg3 are the centroids of the C20–C25, C14–C19 and N1/C1/C10–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯Cg1ⁱ	0.95	2.98	3.8577 (19)	154
C22—H22⋯Cg2ⁱⁱ	0.95	2.94	3.8204 (19)	156
C25—H25⋯Cg3ⁱⁱⁱ	0.95	2.63	3.4738 (17)	148

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

Acknowledgments

We are grateful to the Special Presidential Foundation of Xuzhou Medical College (2010KJZ15) for financial support.

supplementary crystallographic information

Comment

The benzo[h]quinoline derivatives and their complexes can be used as electronic material and organic electronic device (Cho et al. ,2010), potent family-18 chitinase inhibitors (Pantoom et al., 2011), topoisomerase IIα poisons (Liu et al., 2011). Besides, They can also treat Alzheimer's disease. These properties arouse our interset in the relationship between their structures and activities. During the synthesis of benzo[h]quinoline derivatives, the title compound, (I) was isolated and its structure was determined by X-ray diffraction. Herein we shall report its crystal structure. The molecular structure of (I) is shown in Fig. 1. In the molecular structure, the benzo[h]quinoline exhibits a planar conformation with RMS of 0.0202Å and the largest deviation is 0.039 (1) Å. The 3,4-dichlorophenyl is almost coplanar with benzo[h]quinoline, since the dihedral angle between them is only 6.68 (7)°. The parent ring and the phenyl subsitituent at position 4 form a dihedral angle of 67.11 (4)°. In addition, there is a non-classical intramolecular hydrogen bond (C19—H19···N1). The crystal packing is stabilized by the intermolecular C—H···π interactions (Fig. 2, Table 1).

Experimental

The title compound was synthesized according to the reported procedure (Zhang et al., 2010). Under an air atmosphere, a 10 ml of sealable reaction tube equipped with a magnetic stir bar was charged with an 3,4-dichlorobenzaldehyde (1.00 mmol), naphthalen-1-amine (1.00 mmol), and the mixture was heated and stirred in an oil bath at 333 K for 1 h. Then FeCl₃ (16.2 mg, 0.10 mmol), ethynylbenzene (1.10 mmol) were added. The reaction mixture was then stirred in an oil bath at 393 K until the substrates were consumed completely (about 12 h), and then it was cooled to room temperature and the solvent was evaporated, the residue was purified by flash chromatography(hexane/AcOEt = 15:1) to afford the desired product.The single-crystal suitable for X-ray diffraction was obtained through the evaporation of ethanol solution.