A top-down approach to crystal engineering of a racemic Δ2-isoxazoline.
The crystal structure of racemic dimethyl (4RS,5RS)-3-(4-nitrophenyl)-4,5-dihydroisoxazole-4,5-dicarboxylate, C13H12N2O7, has been determined by single-crystal X-ray diffraction. By analysing the degree of growth of the morphologically important crystal faces, a ranking of the most relevant non-covalent interactions determining the crystal structure can be inferred. The morphological information is considered with an approach opposite to the conventional one: instead of searching inside the structure for the potential key interactions and using them to calculate the crystal habit, the observed crystal morphology is used to define the preferential lines of growth of the crystal, and then this information is interpreted by means of density functional theory (DFT) calculations. Comparison with the X-ray structure confirms the validity of the strategy, thus suggesting this top-down approach to be a useful tool for crystal engineering.
Dipartimento di Scienze del Farmaco, Università degli Studi di Catania, Viale Andrea Doria, 6, 95125 Catania, Italy.
Giuseppe M
GM
Lombardo
Dipartimento di Scienze del Farmaco, Università degli Studi di Catania, Viale Andrea Doria, 6, 95125 Catania, Italy.
Antonio
A
Rescifina
Dipartimento di Scienze del Farmaco, Università degli Studi di Catania, Viale Andrea Doria, 6, 95125 Catania, Italy.
Ugo
U
Chiacchio
Dipartimento di Chimica, Università degli Studi di Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy.
Alessia
A
Bacchi
Dipartimento di Scienze del Farmaco, Università degli Studi di Catania, Viale Andrea Doria, 6, 95125 Catania, Italy.
Francesco
F
Punzo
Wulff plot; crystal morphology; density functional theory; periodic bond chain theory