N-Isopropyl-6-methyl-2-phenyl­quinoline-3-carboxamide

Saida Benzerka; Abdelmalek Bouraiou; Sofiane Bouacida; Thierry Roisnel; Ali Belfaitah

doi:10.1107/S1600536810031582

. 2010 Aug 18;66(Pt 9):o2304–o2305. doi: 10.1107/S1600536810031582

N-Isopropyl-6-methyl-2-phenylquinoline-3-carboxamide

Saida Benzerka ^a, Abdelmalek Bouraiou ^a, Sofiane Bouacida ^b,^*, Thierry Roisnel ^c, Ali Belfaitah ^a

PMCID: PMC3008085 PMID: 21588654

Abstract

In the title compound, C₂₀H₂₀N₂O, the dihedral angle between the quinoline ring system and the phenyl ring is 49.40 (5)°. In the crystal structure, zigzag layers of molecules, in which the quinoline units are parallel to the ( Inline graphic 10) plane, are arranged perpendicular to the b axis. Intermolecular N—H⋯O hydrogen bonds connect the molecules into chains along [010], reinforcing the cohesion between the layers of the structure.

Related literature

For our previous work on the preparation of quinoline derivatives, see: Benzerka et al. (2008 ▶); Ladraa et al. (2009 ▶); Bouraiou et al. (2006 ▶, 2008 ▶). For the evaluation of their biological activity, see: Atwell et al. (1988 ▶,1989 ▶); Denny et al. (1990 ▶); Toshima et al. (1999 ▶); Mikata et al. (1998 ▶); Henriksen et al. (1991 ▶). For the synthetic procedure, see: Saudi et al. (2003 ▶).

Experimental

Crystal data

C₂₀H₂₀N₂O
M _r = 304.38
Orthorhombic,
a = 12.0007 (3) Å
b = 9.6314 (2) Å
c = 29.4627 (8) Å
V = 3405.40 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 150 K
0.32 × 0.11 × 0.08 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.747, T _max = 0.994
15315 measured reflections
3906 independent reflections
2839 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.157
S = 1.04
3906 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536810031582/lh5101sup1.cif

e-66-o2304-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031582/lh5101Isup2.hkl

e-66-o2304-Isup2.hkl^{(187.7KB, 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
N2—H2N⋯O1ⁱ	0.88	1.95	2.804 (3)	164

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Symmetry code: (i) Inline graphic .

Acknowledgments

We are grateful to all personel of the PHYSYNOR laboratory, Université Mentouri-Constantine, Algeria, for their assistance.

supplementary crystallographic information

Comment

Since Atwell et al. (1988) and Denny et al. (1990) demonstrated the efficacy of 2 + 1 unfused tricyclic aromatic systems such as phenylquinolines as a minimal intercalators, 2-phenylquinoline (Mikata et al., 1998; Henriksen et al., 1991) was selected as the DNA intercalator. The conjugated C=N bond in the 2-phenylquinoline unit was also expected to generate the photoexcited ³(n→π*) state upon photoirradiation, which may have a radical character and could be capable of cleaving DNA (Toshima et al., 1999). On the other hand, certain 2-phenylquinoline carboxamide derivatives have been shown to possess DNA binding capability and a broad-spectrum activity in both leukemia and solid-tumor assays (Atwell et al., 1989). As part of our program related to the synthesis of some new heterocyclic compounds with medicinal potential (Bouraiou et al.,2006, 2008; Benzerka et al., 2008; Ladraa et al., 2009), we report here the synthesis and crystal structure of the title compound (I). The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The asymmetric unit of title compound contains a quinolyl unit bearing a phenyl ring at position C-2, amide group at C-3 and methyl at C-6. The two rings of the quinolyl moiety are fused in an axial fashion and form a dihedral angle of 3.13 (4)°. The dihedral angle between the phenyl ring quinoline ring system is 49.40 (5)°. The amide group is essentially planar. The r.m.s deviation for atoms C2/C17/O1/N2/C18 is 0.007Å and the maximum deviation is -0.0131 (15)Å for C17. The C—N [1.3260 (17) Å] bond length to the carbonyl group is closer to that of a standard C═N double bond (1.27 Å) than to that of a single bond (1.49 Å). This is because the lone pair electrons on nitrogen of the amide are delocalized into the carbonyl group. The crystal packing can be described as layers in zig zag perpendicular to b axis which quinoline rings are parallel to the (-110) plane (Fig. 2). The crystal packing is stabilized by intermolecular hydrogen bond (N—H···O), resulting in the formation of infinite one-dimensional chain along the b axis linked these layers reinforce the cohesion of the structure (Fig. 2).

Experimental

Compound (I) was obtained from 6-methyl-2-phenylquinoline-3-carboxylic acid and ethyl chloroformate in presence triethylamine in chloroform (Saudi et al., 2003). Suitable crystals for X-ray diffraction were obtained by slow evaporation of a solution of (I) in diisopropylether at room temperature.