Abstract
The hydrated and anhydrous 1:2 cocrystals of oxyresveratrol (4-[(E)-2-(3,5-di-hydroxy-phen-yl)ethen-yl]benzene-1,3-diol; OXY; C14H12O4) and proline [(S)-pyrrolidine-2-carb-oxy-lic acid; PRO; C5H9NO2], namely, 4-[(E)-2-(3,5-di-hydroxy-phen-yl)ethen-yl]benzene-1,3-diol bis-[(S)-pyrrolidin-1-ium-2-carboxyl-ate] monohydrate, C14H12O4·2C5H9NO2·H2O, and the anhydrous form, C14H12O4·2C5H9NO2, were obtained by crystallization at different temperatures. Both of them crystallize with ortho-rhom-bic (P212121) symmetry. The structures display N-H⋯O and O-H⋯O hydrogen-bonding inter-actions between PRO and PRO, OXY and OXY, and OXY and PRO. In the hydrated cocrystal, these types of contacts are also observed between the OXY, PRO and water mol-ecules. A combination of these inter-actions leads to a three-dimensional supra-molecular assembly in each case. Hirshfeld surfaces were used to gain further insight into the inter-molecular inter-actions in the packing, including the relative percentage contributions of the significant inter-molecular H⋯H and H⋯O/O⋯H contacts.
Highlights
Oxyresveratrol (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol; OXY; C14H12O4) is a natural stilbenoid found in various plants, such as Morus alba L. (Lu et al, 2017)
The PRO 1 and PRO 2 molecules form a three-dimensional network of N—HÁ Á ÁO hydrogen bonds between the H atoms of NH2 groups and O atoms of carboxylate groups: N1— H1AÁ Á ÁO6iii, N2—H2AÁ Á ÁO8v and N2—H2BÁ Á ÁO5vi for (I) and N1—H1BÁ Á ÁO5iii, N1—H1AÁ Á ÁO8iv and N2—H2BÁ Á ÁO6vi for (II)
The phenolic hydroxyl groups from the OXY molecule interact with O atoms of the carboxylate groups of the PRO
Summary
Oxyresveratrol (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol; OXY; C14H12O4) is a natural stilbenoid found in various plants, such as Morus alba L. (Lu et al, 2017). Oxyresveratrol (4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,3-diol; OXY; C14H12O4) is a natural stilbenoid found in various plants, such as Morus alba L. Proline [(S)-pyrrolidine-2-carboxylic acid; PRO,; C5H9NO2] is a natural amino acid that has a secondary amino group in the form of a pyrrolydinic ring. It is an osmoprotectant and is used frequently in many pharmacological and biotechnological applications (Panday, 2011). PRO could form a cocrystal with resveratrol [(E)-5-(4-hydroxystyryl)benzene1,3-diol; RES; C14H12O3], which is a close analogue of OXY. PRO is a good candidate as a cocrystal former for cocrystallization with OXY and we describe the syntheses and structures of hydrated and anhydrous 1:2 cocrystals of OXY and PRO, hereafter (I) and (II)
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