3-(4-Chloro­phen­yl)-1-(4-nitro­phen­yl)benzo[f]quinoline

Shu-Liang Wang; Qing Li; Xiang-Shan Wang; Shu-Jiang Tu

doi:10.1107/S1600536809031122

. 2009 Aug 12;65(Pt 9):o2137. doi: 10.1107/S1600536809031122

3-(4-Chlorophenyl)-1-(4-nitrophenyl)benzo[f]quinoline

Shu-Liang Wang ^a,^*, Qing Li ^a, Xiang-Shan Wang ^a, Shu-Jiang Tu ^a

PMCID: PMC2970097 PMID: 21577547

Abstract

In the title compound, C₂₅H₁₅ClN₂O₂, the pyridine ring is inclined at angles of 6.89 (7), 4.24 (9) and 66.98 (4)° with respect to the naphthalene, chlorophenyl and nitrophenyl rings, respectively. The two substituent aromatic rings make a dihedral angle of 71.1 (1)° with one another. C—H⋯π and π–π stacking are present in the crystal structure; the π–π stacking [centroid–centroid distance between the pyridyl rings of adjacent molecules= 3.7838 (11) Å] links the molecules into dimers, while the C—H⋯Cg type π–ring interactons link the molecules into a chain structure along c.

Related literature

Quinoline and its derivatives are intermediates in organic synthesis and are useful dyes, see: Brock et al. (1999 ▶). They possess a broad spectrum of biological activity, such as antiasthmatic, antiinflammatory and antimalarial, see: Fokialakis et al. (2002 ▶); Ma et al. (2004 ▶); Sawada et al. (2004 ▶). In addition, quinoline derivatives have been evaluated as anticancer and anthelmintic agents, see: Sakata et al. (1988 ▶). For related structures, see: Tu et al. (2006 ▶); Xie et al. (2009 ▶).

Experimental

Crystal data

C₂₅H₁₅ClN₂O₂
M _r = 410.84
Triclinic,
a = 9.1390 (12) Å
b = 9.5350 (11) Å
c = 11.9668 (17) Å
α = 108.182 (4)°
β = 105.366 (4)°
γ = 92.739 (3)°
V = 945.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 113 K
0.34 × 0.32 × 0.22 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 1999 ▶) T _min = 0.926, T _max = 0.952
11798 measured reflections
4467 independent reflections
3779 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.129
S = 1.06
4467 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Data collection: CrystalClear (Rigaku, 1999 ▶); 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: CrystalStructure/MSC (Rigaku/MSC (2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809031122/pv2192sup1.cif

e-65-o2137-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031122/pv2192Isup2.hkl

e-65-o2137-Isup2.hkl^{(218.8KB, 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
C24—H24⋯Cgⁱ	0.95	2.72	3.510 (12)	142

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Symmetry code: (i) Inline graphic . Cg is the centroid of the C14–C19 ring.

Acknowledgments

We are grateful to the Natural Science Foundation (08KJD150019) and the Qing Lan Project (08QLT001) of Jiangsu Education Committee for financial support.

supplementary crystallographic information

Comment

Quinoline and its derivatives represent an important class of nitrogen-containing heterocycles as they constitute useful intermediates in organic synthesis and are useful dyes (Brock et al., 1999). They are well known in the pharmaceutical industry and have been shown to possess a broad spectrum of biological activities including such as antiasthmatic, antiinflammatory and antimalarial activity (Sawada, et al., 2004; Ma et al., 2004; Fokialakis et al., 2002). In addition, quinoline derivatives have been evaluated as anticancer and anthelmintic agents (Sakata et al., 1988). We report here the preparation and crystal structure of 3-(4-chlorophenyl)-1-(4-nitrophenyl)benzo[f]quinoline, (I).

In the structure of (I) (Fig. 1), the benzoquinoline moiety is not quite planar as C3 deviates by 0.169 (1) Å from the mean-plane formed by the atoms N1/C1–C13. The pyridine ring is inclined at angles 6.89 (7), 4.24 (9) and 66.98 (4) ° with respect to the naphthalene (C4–C13), and phenyl rings C14–C19 and C20–C25, respectively. The two phenyl rings make a dihedral angle of 71.1 (1) °.

The C—H···π and π–π stacking are present in the crystal structure of (I). The π–π stacking (Cg···Cg distance 3.7838 (11) Å between the pyridyl rings of adjacent molecules) links the molecules into dimmers, while the C24—H24A···Cg stacking links the molecules into polymers (Figure 2).

The following crystal structures of compounds closely related to (I) have been reported: 13-(4-fluorophenyl)-12H-benzo[f]indeno[1,2-b]quinolin-12-one (Tu et al., 2006) and 5-(4-bromophenyl)-1,2,3,4-tetrahydrobenzo[a]phenanthridine (Xie et al., 2009).

Experimental

The title compound, (I), was prepared by the reaction of 4-chlorobenzaldehyde (2 mmol, 0.281 g), naphthalen-2-amine (2 mmol, 0.283 g) and 2-bromoacetophenone (2 mmol, 0.498 g) in THF (10 ml) at 338 K catalyzed by iodine. m.p. 559–561 K. The single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution of (I).