7-(3-Nitro­phen­yl)-9,10-dihydro-7H-benzo[h]cyclo­penta­[b]quinolin-8(11H)-one

Tuanjie Li; Honghong Zhang

doi:10.1107/S1600536811043546

. 2011 Oct 29;67(Pt 11):o3068. doi: 10.1107/S1600536811043546

7-(3-Nitrophenyl)-9,10-dihydro-7H-benzo[h]cyclopenta[b]quinolin-8(11H)-one

Tuanjie Li ^a,^*, Honghong Zhang ^a

PMCID: PMC3247459 PMID: 22220077

Abstract

In the title compound, C₂₂H₁₆N₂O₃, the naphthalene ring, the 1,4-dihydropyridine ring and the cyclopent-2-enone ring are nearly coplanar, with the dihedral angles between the neighbouring rings being 1.93 (11) and 2.30 (9)°, respectively. The benzene ring group at position 7 and the 1,4-dihydropyridine ring form a dihedral angle of 78.75 (4)°. Intermolecular N—H⋯O hydrogen bonds and C—H⋯π interactions stabilize the crystal packing.

Related literature

For the medicinal use of 1,4-dihydropyridine derivatives, see: Zheng et al. (2011 ▶); Ginsberg & Kummer (2011 ▶); Nadaraj et al. (2009 ▶); Husson et al. (2011 ▶). For the preparation of the title compound, see: Heravi et al. (2010 ▶).

Experimental

Crystal data

C₂₂H₁₆N₂O₃
M _r = 356.37
Monoclinic,
a = 10.256 (1) Å
b = 13.7570 (14) Å
c = 11.9830 (12) Å
β = 104.827 (5)°
V = 1634.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 113 K
0.24 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku/MSC, 2009 ▶) T _min = 0.977, T _max = 0.983
16937 measured reflections
3897 independent reflections
3094 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.130
S = 1.12
3897 reflections
248 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClearSM Expert (Rigaku/MSC, 2009 ▶); cell refinement: CrystalClearSM Expert; data reduction: CrystalClearSM Expert; 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/S1600536811043546/hg5109sup1.cif

e-67-o3068-sup1.cif^{(21KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043546/hg5109Isup2.hkl

e-67-o3068-Isup2.hkl^{(191KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811043546/hg5109Isup3.cml

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

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

Cg is the centroid of the ring of C11–C16.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.881 (19)	2.07 (2)	2.9307 (17)	165.9 (18)
C21—H21⋯Cgⁱⁱ	0.95	2.69	3.5090 (19)	145

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

supplementary crystallographic information

Comment

The 1,4-dihydropyridine (1,4-DHP) derivatives exhibits various bioactivities, including sedative-hypnotic activity (Zheng et al. 2011), inhibition of the α 4-integrin-paxillin interaction (Ginsberg et al. 2011), anti-microbial activities (Nadaraj et al. 2009),and antitumor activity (Husson et al. 2011). These reports inspired us to study the relationship between their structures and activities. During the synthesis of 1,4-dihydropyridine (1,4-DHP) derivatives, the title compound, (I) was isolated and its structure was determined by X-ray diffraction. Herein we report its crystal structure.

In the molecular structure (Fig. 1), the naphthalene ring, the 1,4-dihydropyridine ring and the cyclopent-2-enone ring adopt planar conformations with RMS of 0.0201 Å, 0.0235 Å and 0.0058 Å, respectively. The largest deviation of these rings are 0.033 (1) Å(C2), 0.038 (1) Å(C3), 0.008 (1) Å(C5), respectively. The fused ring system is almost coplanar, for the dihedral angle between the neighboring rings are 1.93 (0.11) ° and 2.30 (9)° respectively. The planar 3-nitrophenyl ring at position 7 and the 1,4-dihydropyridine ring forms a dihedral angle of 78.75 (4)°. The crystal packing is stablized by the intermolecular N—H···O hydrogen bond and C—H···π interactions (Fig. 2, Table 1).

Experimental

The title compound was synthesized according to the procedure (Heravi et al. 2010). A round-bottomed flask was charged with 3-nitrobenzaldehyde (1 mmol), cyclopentane-1,3-dione (1 mmol), 1-naphtylamine (1 mmol), acetic acid (5 ml), and H₆P₂W₁₈O_62.18H₂O (0.01 mmol). The reaction mixture was stirred until completion (monitored by TLC). Then the mixture was poured into ice water. The precipitated products were separated by filtration, washed with water, recrystallized in a dimethylformamide-ethanol (DMF-EtOH) solution. The recrystallization gave single-crystals suitable for X-ray diffraction.