7-p-Tolyl-10,11-dihydro­benzo[h]furo[3,4-b]quinolin-8(7H)-one

Chunling Shi

doi:10.1107/S160053681000591X

. 2010 Feb 20;66(Pt 3):o668. doi: 10.1107/S160053681000591X

7-p-Tolyl-10,11-dihydrobenzo[h]furo[3,4-b]quinolin-8(7H)-one

Chunling Shi ^a,^*

PMCID: PMC2983703 PMID: 21580416

Abstract

In the title compound, C₂₂H₁₇NO₂, the fused ring system is essentially planar (r.m.s. deviation = 0.021 Å) and the dihedral angle between the dihydropyridine and tolyl rings is 80.98 (11)°. In the crystal, the molecules are linked into chains along the b axis by intermolecular N—H⋯O and C—H⋯O hydrogen bonds. Adjacent chains are linked by π–π interactions [centroid–centroid separation = 3.5748 (15) Å].

Related literature

For the biological activity of podophyllotoxin and its derivatives, see: Bosmans et al. (1989 ▶); Eycken et al. (1989 ▶); Hitosuyanagi et al. (1997 ▶, 1999 ▶); Lienard et al. (1991 ▶); Magedov et al. (2007 ▶); Poli & Giambastiani (2002 ▶); Tomioka et al. (1989 ▶, 1993 ▶); Tratrat et al. (2002 ▶). For a related structure, see: Shi & Ji (2009 ▶).

Experimental

Crystal data

C₂₂H₁₇NO₂
M _r = 327.37
Monoclinic,
a = 10.6954 (16) Å
b = 13.0566 (18) Å
c = 12.183 (2) Å
β = 107.322 (3)°
V = 1624.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 223 K
0.60 × 0.34 × 0.30 mm

Data collection

Rigaku Mercury diffractometer
Absorption correction: multi-scan (Jacobson, 1998 ▶) T _min = 0.770, T _max = 0.975
15611 measured reflections
2978 independent reflections
2476 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.138
S = 1.18
2978 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrystalClear (Rigaku, 2000 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003 ▶); 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 datablocks global, I. DOI: 10.1107/S160053681000591X/ci5030sup1.cif

e-66-0o668-sup1.cif^{(20.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000591X/ci5030Isup2.hkl

e-66-0o668-Isup2.hkl^{(146.2KB, 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
N1—H1⋯O2ⁱ	0.87	2.00	2.802 (2)	153
C12—H12⋯O1ⁱ	0.94	2.49	3.248 (3)	137

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author thanks the Scientific Research Item of Xuzhou Institute of Technology (grant No. XKY2009114) for financial support.

supplementary crystallographic information

Comment

Podophyllotoxin is an antitumor lignan that inhibits microtubule assembly (Eycken et al., 1989; Tomioka et al., 1989; Bosmans et al., 1989). Extensive structural modifications have been performed in order to obtain more potent and less toxic anticancer agents (Tomioka et al., 1993; Lienard et al., 1991; Poli et al., 2002). Among them, 4-aza-podophllotoxin (9-aryl-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one) derivatives reported as powerful DNA topoisomerase II inhibitors, have recently attached considerable interest (Hitosuyanagi et al., 1997; Hitosuyanagi et al., 1999; Tratrat et al., 2002; Magedov et al., 2007). We report here the crystal structure of the title compound, which was synthesized by the three-component reaction of naphthalen-1-amine with 4-methylbenzaldehyde and tetronic acid catalyzed by L-proline using ethanol as solvent at 353 K.

In the title compound, the 1,4-dihydropyridine (C1–C5/N1) and furanone rings are planar (Fig. 1) and both are coplanar with the naphthalene ring system i.e the fused ring system is essentially planar (r.m.s. deviation 0.021 Å). The dihedral angle between C1–C5/N1 and C16–C21 planes is 80.98 (11)°. The conformation of the title molecule differs from that of a related molecule, 7-methyl-9-p-tolyl-4,9-dihydrofuro[3,4-b]quinolin-1(3H)-one (Shi et al., 2009).

In the crystal structure, the molecules are linked by N1—H1···O2 and C12—H12···O1 intermolecular hydrogen bonds (Table 1) to form chains (Fig. 2) along the b axis. The adjacent chains are linked through π-π interactions between O1/C14/C4/C5/C15 and C1/C2/C6-C8/C13 rings with a centroid-centroid separation of 3.5748 (15) Å.

Experimental

The title compound was prepared by the reaction of naphthalen-1-amine (1 mmol) and 4-methylbenzalhyde (1 mmol) with tetronic acid (1 mmol) in the presence of L-proline (0.1 mmol) in ethanol (2 ml) at 353 K. Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of a N,N-dimethylformamide and ethanol solution. ¹H NMR (DMSO-d₆, δ): 2.21 (3H, s, CH₃), 4.98 (1H, d, J = 16.0 Hz, CH₂), 5.07 (1H, d, J = 16.0 Hz, CH₂), 5.13 (1H, s, CH), 7.05 (2H, d, J = 8.0 Hz, ArH), 7.12 (3H, dd, J₁ = 6.4 Hz, J₂ = 8.0 Hz, ArH), 7.46 (1H, d, J = 8.8 Hz, ArH), 7.51-7.55 (1H, m, ArH), 7.60-7.64 (1H, m, ArH), 7.84 (1H, d, J = 8.0 Hz, ArH), 8.21 (1H, d, J = 8.0 Hz, ArH), 10.22 (1H, s, NH).