Copyright © Hassan et al. 2008
Quinoxalin-2-yl o-tolyl ether
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng/at/um.edu.my
Received August 12, 2008; Accepted August 19, 2008.
This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The dihedral angle between the two aromatic ring systems in the title compound, C15H12N2O, is 85.9 (1)°; The angle at the O atom is widened to 118.2 (2)°. The quinoxalinyloxy part of the molecule lies on a mirror plane and the tolyl group is disordered over two positions about the mirror plane.
Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).
We thank the University of Malaya for supporting this study (grant No. F2358/2008 A).
supplementary crystallographic information
o-Cresol (0.54 g, 5 mmol) was dissolved in a small volume of water containing potassium hydroxide (0.20 g, 5 mmol). The mixture was heated to remove the water to give a brown compound. The compound and 2-chloroquinoxaline (0.82, g, 5 mmol) were heated in THF (15 ml) for 8 h. The mixture was in 1 N sodium hydroxide; the aqueous solution was extracted with dichloromethane. The organic phase was dried over sodium sulfate. Evaporation of the solvent gave a yellow product, which was was washed with chloroform to remove impurities. Crystals were obtained upon recrystallization from an ethyl acetate/hexane mixture.
The tolyl group is disordered about a mirror plane; the phenylene ring was refined as a rigid hexagon. The seven carbon atoms were allowed to refine off the symmetry element; the atoms were all given 0.5 site occupancy.
H-atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) fixed at 1.2–1.5U(C).
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, °)
Symmetry codes: (i) x, −y+1/2, z.