(4-Nitrophenolato)(subphthalocyaninato)boron(III)1

The main feature of the structure of the title compound, C30H16BN7O3 or NO2PhO-BsubPc, are pairs of molecules linked through π-interactions between the concave faces of the BsubPc fragments at a distance of 3.5430 (11) Å across an inversion centre. However, the angle between the planes of the five- and six-menbered rings involved in this interaction is 1.44 (10)°, causing the interacting BsubPcs units to be slightly askew rather than parallel as is typical for π-stacking interactions.

The main feature of the structure of the title compound, C 30 H 16 BN 7 O 3 or NO 2 PhO-BsubPc, are pairs of molecules linked through -interactions between the concave faces of the BsubPc fragments at a distance of 3.5430 (11) Å across an inversion centre. However, the angle between the planes of the five-and six-menbered rings involved in this interaction is 1.44 (10) , causing the interacting BsubPcs units to be slightly askew rather than parallel as is typical for -stacking interactions.

Comment
We report the crystal structure of 4-nitrophenoxy-boronsubphthalocyanine (NO 2 PhO-BsubPcs), which possesses an electron withdrawing group in the para position of the phenoxy molecular fragment. We have recently reported a study of the crystal structures of a series of para-substituted phenoxy-BsubPcs wherein most of the substituents were electron donating (alkyl, Paton et al., 2010). Contained within the study was 4-fluorophenoxy-BsubPcs (FPhO-BsubPcs). While fluorine is moderately electron withdrawing we did not observe any difference in its crystal structure compared to the baseline phenoxy-BsubPcs. We have since reported the structure of a derivative with a stronger electron withdrawing group, 4-acetylphenoxy-BsubPcs. (Paton et al., 2011) This structure was only slightly different from the typical FPhO-BsubPcs crystal packing motif. We synthesized the title compound as the next derivative in a series studying the effects of electron withdrawing groups on related compounds.
The title compound was prepared by a method described previously (Paton et al., 2010;Claessens et al., 2003), in which chloro-boronsubphthalocyanine (Cl-BsubPcs) is reacted with an excess of the appropriate phenol until substitution is complete. Further details are given in the experimental sections which accompany this article.
The molecular structure of the title compound obtained from benzene-heptane diffusion crystallization is shown in gives values of -44.7 (3)°. In contrast, the angle associated with FPhO-BsubPcs is -91.0 (2)° relative to the plane of the BsubPcs fragment (Paton et al., 2010).
The crystal structure of NO 2 PhO-BsubPcs ( Fig. 2) shows pairs of BsubPcs fragments associated through a π-interaction separated by a centroid-to-centroid distance of 3.5430 (11) Å. These pairs of molecules form one-dimensional rows aligned with the b axis. The π-interaction creating the pairs is between two sets of BsubPcs fragments whose ring planes are not perfectly parallel; the planes of the two rings (C9/C10/C11/C12/C13/C14/C15 and C9/C10/C15/C16/N3 on neighbouring molecules) are at an angle of 1.44 (10)°.