Ethyl 5-cyano-8-nitro-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline-5-carboxylate

Yapi Marcellin Yapo; Kouakou Michel Konan; Ané Adjou; Adéyolé Timotou; Jules A Tenon

doi:10.1107/S160053681002283X

. 2010 Jun 23;66(Pt 7):o1735. doi: 10.1107/S160053681002283X

Ethyl 5-cyano-8-nitro-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline-5-carboxylate

Yapi Marcellin Yapo ^a,^*, Kouakou Michel Konan ^a, Ané Adjou ^b, Adéyolé Timotou ^b, Jules A Tenon ^a

PMCID: PMC3006821 PMID: 21587952

Abstract

In the title compound, C₁₇H₁₉N₃O₄, the piperidine ring adopts a chair conformation. The crystal structure features inversion dimers linked by pairs of weak C—H⋯N hydrogen bonds.

Related literature

For the therapeutic properties of quinoline derivatives, see: Dalla Via et al. (2008 ▶); Gasparotto et al. (2006 ▶); Ferlin et al. (2000 ▶). A similar heterocyclic structure, Mitomycin C, is used in cancer therapy, see: Crooke & Bradner (1976 ▶); Danishefsky & Ciufolini (1984 ▶); Remers (1980 ▶). For related structures, see: Zhuravleva et al. (2009 ▶); Oliveira et al. (2006 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₇H₁₉N₃O₄
M _r = 329.36
Triclinic,
a = 8.8257 (4) Å
b = 9.2256 (5) Å
c = 10.5011 (6) Å
α = 88.246 (4)°
β = 75.089 (2)°
γ = 83.289 (3)°
V = 820.57 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 223 K
0.20 × 0.20 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
10064 measured reflections
4189 independent reflections
2794 reflections with I > 2σ(I)
R _int = 0.04

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.096
S = 1.04
2503 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: CRYSTALS.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002283X/bq2218sup1.cif

e-66-o1735-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002283X/bq2218Isup2.hkl

e-66-o1735-Isup2.hkl^{(209.3KB, 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
C7—H72⋯N3ⁱ	0.97	2.56	3.492 (3)	161

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors wish to thank the Laboratoire de Physique des Interactions Ioniques et Moléculaires of Provence University (France) for the use of the diffractometer.

supplementary crystallographic information

Comment

Tricyclic quinoline derivatives have diverse and important therapeutic properties (Dalla Via et al., 2008; Gasparotto et al., 2006; Ferlin et al., 2000). These heterocyclic are similar to Mitomycin C which is a powerful antibiotic used in cancerous chemotherapy (Crooke et al., 1976; Remers et al., 1980; Danishefsky et al., 1984). They are also used as intermediate compound to elaborate keratic fiber colorings. Here, we report the single X-ray determination of the title compound C₁₇H₁₉N₃O₄, (I), in order to have a best insight of its structure and then to undertake a study of its possible therapeutic activity. The molecular structure of this compound and its atomic labeling scheme are shown in Figure 1. The bond lenghts distances are within the accepted range (Allen et al., 1987). In (I), there are two coupled rings: quinoline and piperidine rings. The geometrical characteristics relating bond distances in quinoline ring are consistent and present no particularity with the recently reported (Oliveira et al., 2006; Zhuravleva et al., 2009). By least squares planes method, it is observed that carbon atom C8 deviates of -0.4074Å to quinoline cycle plane what proves that quinoline ring is not veritably plane. Concerning piperidine ring, it assumes a chair conformation which the puckering parameters (Cremer & Pople, 1975): θ=7.78°, Q=0.6147Å and Φ=42.46°. The crystal packing is due to the weak hydrogen bonds C-H···N which ensure crystal cohesion (Table 1 and Figure 2).

Experimental

3.5 g, 10 mmol of malonic arylidene was dissolved in 10 ml of dimethylformamide. The melange was heated to reflux during 24 h. After cooling to ambient temperature, 20 ml of water was added to the melange. After extraction to ethyl acetate (150 ml), the organic layers were dried on magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel using hexane/ethyl acetate (80/20) to obtain yellow crystals with 45% yields. The melting point is 424 K