Date Published: July 01, 2012
Publisher: International Union of Crystallography
Author(s): Yee Jan Chin, Ai Ling Tan, Franz L. Wimmer, Aminul Huq Mirza, David J. Young, Seik Weng Ng, Edward R. T. Tiekink.
In the title compound, C11H6N2O, the complete molecule is generated by the application of crystallographic twofold symmetry (the molecule is disordered about this axis). The prop-2-yn-1-yl residue is slightly twisted out of the plane of the benzene ring [C—O—C—C torsion angle = 173.1 (3)°] and is orientated away from the nitrile substituents. In the crystal, supramolecular chains along the a axis, arising from C—H⋯N interactions, are connected into stacks along the c axis by π–π interactions between the benzene rings [centroid–centroid distance = 3.6978 (6) Å = length of the c axis].
For the solubilization and some applications of phthanocyanine dyes, see: Jiang et al. (2011 ▶); Sleven et al. (2001 ▶). For the synthesis of substituted phthalonitriles, see: Wöhrle et al. (1993 ▶); Wu et al. (1998 ▶); Li & Lieberman (2001 ▶); Sleven et al. (2001 ▶); Li et al. (2008 ▶); Seven et al. (2009 ▶); Foo et al. (2012 ▶).