4-(4-Bromo­phen­yl)-2,3,3a,4,5,11c-hexa­hydro­benzo[f]furo[3,2-c]quinoline

Nan Wu; Rongli Zhang; Xinnian Li; Xin Xu; Zhou Xu

doi:10.1107/S1600536811031084

. 2011 Aug 11;67(Pt 9):o2285. doi: 10.1107/S1600536811031084

4-(4-Bromophenyl)-2,3,3a,4,5,11c-hexahydrobenzo[f]furo[3,2-c]quinoline

Nan Wu ^a, Rongli Zhang ^b, Xinnian Li ^a, Xin Xu ^a, Zhou Xu ^b,^*

PMCID: PMC3200627 PMID: 22065710

Abstract

In the title compound, C₂₁H₁₈BrNO, both heterocyclic rings, viz. the hydropyridine ring and the adjacent hydrofuran ring, adopt envelope conformations. These two heterocycles make a dihedral angle of 37.3 (1)°. The dihedral angle between the hydropyridine and benzene rings is 69.6 (1)°. In the crystal, adjacent molecules are linked by pairs of intermolecular C—H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For the biological properties of quinoline derivatives, see: Nesterova et al. (1995 ▶); Yamada et al. (1992 ▶); Faber et al. (1984 ▶); Johnson et al. (1989 ▶). For related structures, see: Ramesh et al. (2008 ▶); Zhao & Teng (2008 ▶); Bai et al. (2009 ▶); Du et al. (2010 ▶); Wang et al. (2010 ▶).

Experimental

Crystal data

C₂₁H₁₈BrNO
M _r = 380.27
Triclinic,
a = 9.4019 (2) Å
b = 9.6025 (2) Å
c = 10.4660 (2) Å
α = 103.888 (1)°
β = 114.075 (1)°
γ = 92.469 (1)°
V = 826.81 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.49 mm⁻¹
T = 296 K
0.20 × 0.09 × 0.04 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.793, T _max = 0.899
10901 measured reflections
2921 independent reflections
2301 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.076
S = 1.04
2921 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536811031084/zb2015sup1.cif

e-67-o2285-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031084/zb2015Isup2.hkl

e-67-o2285-Isup2.hkl^{(143.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811031084/zb2015Isup3.cml

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
C9—H9⋯O1ⁱ	0.93	2.69	3.462 (3)	141

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to the Special Presidential Foundation of Xuzhou Medical College (2010KJZ24) for financial support.

supplementary crystallographic information

Comment

Quinoline derivatives has been extensively studied due to its 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). 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), the hydropyridine ring of the furoquinoline moiety adopts an envelope conformation (Fig. 1). The atom C1 deviates from the plane defined by the atoms C2/C5/C6/C15/N1 by 0.646 (3) Å. This conformation is different from those reported in other hydropyridine derivatives (For related structrues, see Ramesh, et al., 2008; Zhao & Teng, 2008; Bai et al., 2009; Du, et al., 2010). In the adjacent hydrofuran ring, the atoms C2—C4 and O1 are coplanar, while the atom C5 deviates from the plane by 0.522 (3) Å. This data indicates that the above hydrofuran ring also adopts an envelope conformation. These two heterocycles make a dihedral angle of 37.3 (1)°. The basal plane of the hydropyridine ring is nearly coplanar to the naphthalene ring C6—C15, forming a dihedral angle of 6.0 (1)°. The dihedral angle between the phenyl and the hydropyridine ring is 69.6 (1)°. The hydrogen bond of C9—H9···O1 links the adjacent moleclues forming dimmers along a axis (Figure 2). This hydrogen bonding pattern is same with the one reported in literature (Wang et al., 2010).

Experimental

The title compound, (I), was prepared by the reaction of 4-bromobenzaldehyde (0.361 g, 2.0 mmol), naphthalen-2-amine (0.286 g, 2.0 mmol), 2,3-dihydrofuran (0.252 g, 3.0 mmol), I₂ (0.026 g, 0.1 mmol) and THF (10 ml) for 18 h (yield 87%, mp. 523–525 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a DMF solution.