2-(4-Bromo­phen­yl)quinoxaline

Zhi-jian Wang; Wei-min Jia; Hong-guo Yao; Hong Qiu; Wei Wang

doi:10.1107/S160053681001723X

. 2010 May 19;66(Pt 6):o1380. doi: 10.1107/S160053681001723X

2-(4-Bromophenyl)quinoxaline

Zhi-jian Wang ^a, Wei-min Jia ^a, Hong-guo Yao ^b, Hong Qiu ^b, Wei Wang ^a,^b,^*

PMCID: PMC2979498 PMID: 21579461

Abstract

In the title compound, C₁₄H₉BrN₂, the benzene and quinoxaline rings are almost coplanar [r.m.s. deviation = 0.0285 (3) Å and dihedral angle = 2.1 (2)°].

Related literature

For the synthesis of quinoxaline derivatives, see: Raw et al. (2003 ▶); Bhosale et al. (2005 ▶). For their applications, see: Brock et al. (1999 ▶); Seitz et al. (2002 ▶); He et al. (2003 ▶). For typical bond lengths in a related structure, see: Rong et al. (2006 ▶).

Experimental

Crystal data

C₁₄H₉BrN₂
M _r = 285.14
Monoclinic,
a = 13.959 (3) Å
b = 5.9031 (12) Å
c = 14.497 (3) Å
β = 109.53 (3)°
V = 1125.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 3.63 mm⁻¹
T = 153 K
0.20 × 0.18 × 0.10 mm

Data collection

Rigaku MM-OO7/Saturn 70 CCD area-detector diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T _min = 0.531, T _max = 0.713
8910 measured reflections
2683 independent reflections
1763 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.075
S = 0.96
2683 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.76 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S160053681001723X/zs2039sup1.cif

e-66-o1380-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001723X/zs2039Isup2.hkl

e-66-o1380-Isup2.hkl^{(131.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We gratefully acknowledge support of this work by the Key Laboratory Project of Liaoning Province (No. 2008S127) and the Doctoral Starting Foundation of Liaoning Province (No. 20071103).

supplementary crystallographic information

Comment

Quinoxaline derivatives are an important class of nitrogen containing heterocycles, finding use as intermediates in organic synthesis and in addition have been reported as having applications as anticancer, antiviral, and antibacterial agents (Seitz et al., 2002; He et al., 2003) and dyes (Brock et al., 1999). In recent years, many syntheses of quinoxaline derivatives have been reported (Raw et al., 2003; Bhosale et al., 2005). The title compound C₁₄H₉BrN₂ (I) is one of such quinoxaline derivates which we have synthesized and now report its crystal structure.

The molecular structure of title compound is as shown in Fig.1. The bond lengths and angles are usual for this type of compound (Rong et al., 2006). The dihedral angle between the benzene ring and quinoxaline ring is 2.1 (2)°, which means that the benzene ring and the quinoxaline ring are approximately coplanar with a r.m.s deviation of 0.0285 (3) Å, the Br atom lying in the plane of the substituent benzene ring [r.m.s deviation, 0.0271 (3) Å]. The crystal packing (Fig. 2) is stabilized by van der Waals forces.

Experimental

A suspension of hydrated 2-(4-bromophenyl)-2-oxoacetaldehyde (2.0 mmol) and benzene-1,2-diamine (3.0 mmol) in ethanol (5 ml) was stirred at room temperature with the reaction progress monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the title compound as a light yellow solid (92.5% yield: m.p. 418 K). Crystals suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).