1-Benzyl-3-methyl­quinoxalin-2(1H)-one

Youssef Ramli; Ahmed Moussaif; Hafid Zouihri; Saïd Lazar; E M Essassi

doi:10.1107/S1600536810025614

. 2010 Jul 7;66(Pt 8):o1922. doi: 10.1107/S1600536810025614

1-Benzyl-3-methylquinoxalin-2(1H)-one

Youssef Ramli ^a,^*,^‡, Ahmed Moussaif ^a,^§, Hafid Zouihri ^b, Saïd Lazar ^c, E M Essassi ^a

PMCID: PMC3007303 PMID: 21588252

Abstract

The asymmetric unit of the title compound, C₁₆H₁₄N₂O, contains three independent molecules. The dihedral angles between the quinoxaline and phenyl planes in the three molecules are 82.58 (8), 85.66 (9) and 85.36 (9)°. The crystal packing is stabilized by C—H⋯O and C—H⋯N hydrogen bonds.

Related literature

For the biological activity of quinoxaline derivatives, see: Kleim et al. (1995 ▶); Abasolo et al. (1987 ▶); Rodrigo et al. (2002 ▶); Jampilek et al. (2005 ▶); Sashidhara et al. (2009 ▶); Watkins et al. (2009 ▶).

Experimental

Crystal data

C₁₆H₁₄N₂O
M _r = 250.29
Triclinic,
a = 7.4433 (2) Å
b = 17.5444 (5) Å
c = 18.0598 (7) Å
α = 118.034 (2)°
β = 100.217 (2)°
γ = 92.726 (1)°
V = 2025.27 (11) Å³
Z = 6
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.25 × 0.21 × 0.15 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer
46425 measured reflections
9750 independent reflections
6445 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.166
S = 1.09
9750 reflections
516 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025614/pv2301sup1.cif

e-66-o1922-sup1.cif^{(31.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025614/pv2301Isup2.hkl

e-66-o1922-Isup2.hkl^{(476.8KB, 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
C125—H125⋯N12ⁱ	0.93	2.62	3.423 (2)	145
C321—H321⋯O1ⁱⁱ	0.93	2.56	3.320 (3)	140
C325—H325⋯N32ⁱⁱⁱ	0.93	2.51	3.380 (3)	155

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

Acknowledgments

The authors thank the CNRST of Morocco for making this work possible.

supplementary crystallographic information

Comment

Quinoxaline derivatives are an important class of nitrogen containing heterocycles in medicinal chemistry. They exhibit antimicrobial (Kleim et al., 1995), antitumor (Abasolo et al., 1987), and antituberculous activity (Rodrigo et al., 2002]. They also exhibit antifungal, herbicidal, antidyslipidemic and antioxidative activities (Jampilek et al., 2005; Sashidhara et al., 2009; Watkins et al., 2009). In this paper, the synthesis and crystal structure of the title compound is presented.

The asymmetric unit of the title compound contains three independent molecules (Fig. 1). The dihedral angles between the quinoxaline and phenyl planes in the three molecules are 82.58 (8), 85.66 (9) and 85.36 (9)°. The crystal structure is devoid of classical hydrogen bonds. However, the crystal packing is stabilized by C—H···O and C—H···N hydrogen bonds (Tab. 1 & Fig. 2).

Experimental

To a solution of 3-methylquinoxali-2(1H)-one (1 g) in 20 ml of dimethylformamide were added benzylchloride (0.72 ml), K₂CO₃ (0.90 g) and catalytic amont of tetrabutylammonium bromide. The mixture was stirred at room temperature for 24 h. The solvent was removed under reduce pressure and the residue was crystallized in ethanol to afford the crystals of the title compound which were suitable for X-ray analysis.