In the present study, we build on these previous works by demonstrating the use of CSP in screening a large set of molecules with mixed hydrogen bond donors and acceptors as candidates for small molecule crystalline organic semiconductors. Our study is motivated by the recent report of (pyrido [2,3-b]pyrido [3 ,2 :4,5]pyrrolo[3,2-g]indole) (1, Fig. ), a planar, extended aromatic molecule with C 2v symmetry. 1 adopts a γ-type crystal packing, which features columns of π-stacked molecules, with two orientations of such columns forming a 'cruciform' arrangement. The crystal packing in 1 is directed by hydrogen bonds between the two hydrogen bond donors (-NH from the pyrrole rings) and acceptors (N from pyridine rings). Charge transport calculations on this structure suggested good carrier mobility in the directions of the molecular stacks.