1-(2-Methyl-6-nitro-4-phenyl-3-quinol­yl)ethanone

Wan-Sin Loh; Hoong-Kun Fun; K Kiran; S Sarveswari; V Vijayakumar

doi:10.1107/S1600536810015473

. 2010 Apr 30;66(Pt 5):o1237. doi: 10.1107/S1600536810015473

1-(2-Methyl-6-nitro-4-phenyl-3-quinolyl)ethanone

Wan-Sin Loh ^a,^‡, Hoong-Kun Fun ^a,^*,^§, K Kiran ^b, S Sarveswari ^b, V Vijayakumar ^b

PMCID: PMC2979093 PMID: 21579257

Abstract

In the title compound, C₁₈H₁₄N₂O₃, the quinoline ring system is almost planar [maximum deviation = 0.013 (2) Å] and forms a dihedral angle of 60.36 (7)° with the benzene ring. The nitro group is slightly twisted from the attached quinoline ring system, forming a dihedral angle of 9.06 (19)°. In the crystal packing, intermolecular C—H⋯O hydrogen bonds link the molecules into chains propagating in [010].

Related literature

For related structures, see: Fun et al. (2009 ▶); Loh et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₈H₁₄N₂O₃
M _r = 306.31
Monoclinic,
a = 13.297 (2) Å
b = 7.7689 (12) Å
c = 17.9430 (19) Å
β = 129.099 (7)°
V = 1438.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.48 × 0.33 × 0.24 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.954, T _max = 0.977
14926 measured reflections
4148 independent reflections
3310 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.061
wR(F ²) = 0.232
S = 1.13
4148 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015473/hb5399sup1.cif

e-66-o1237-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015473/hb5399Isup2.hkl

e-66-o1237-Isup2.hkl^{(203.3KB, 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
C3—H3A⋯O2ⁱ	0.93	2.56	3.208 (3)	127

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). WSL thanks the Malaysian Government and USM for the award of a Research Fellowship. VV is grateful to DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

supplementary crystallographic information

Comment

In continuation of our interest in the synthesis and structures of quinolines (Fun et al., 2009; Loh et al., 2009), we now report the title compound, (I).

In the title compound (Fig. 1), the quinoline ring system (C1/N1/C2–C9) is approximately planar with a maximum deviation of 0.013 (2) Å at atom C5. This mean plane of the quinoline ring forms a dihedral angle of 60.36 (7)° with the benzene ring (C10–C15). The nitro group (N2/O2/O3) is slightly twisted from the attached quinoline ring system, forming a dihedral angle of 9.06 (19)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to closely related structures (Fun et al., 2009; Loh et al., 2009).

In the crystal packing (Fig. 2), intermolecular C3—H3A···O2 hydrogen bonds (Table 1) linked the molecules into chains linking down the b axis.

Experimental

A mixture of 5-nitro-2-amino-benzophenone (0.01 M) acetylacetone (0.01 M) and 0.15 ml of concentrated HCl was irradiated under microwave for about 8 min at 240 W. The resultant solid was filtered, dried and purified by column chromatography using 1:1 mixture of ethyl acetate and petroleum ether. M.P.: 403 K. Yield: 60%. Yellow blocks of (I) were recrystallised from chloroform.