Crystal structures of four organic salts of trihexyphenidyl at 90 K

Vinaya and Basavaraju, Y. B. and Yathirajan, H. S. and Parkin, Sean (2023) Crystal structures of four organic salts of trihexyphenidyl at 90 K. Acta Crystallographica Section E, 79 (8). pp. 730-735. ISSN 2056-9890

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Official URL: https://doi.org/10.1107/S2056989023005960

Abstract

The syntheses and crystal structure studies of four organic salts of trihexyphenidyl, viz., trihexyphenidylium [1-(3-cyclo­hexyl-3-hy­droxy-3-phenyl­prop­yl)piperidin-1-ium] 4-nitro­benzoate, C20H32NO+·C7H4NO4− (I), trihexyphenidylium 4-hy­droxy­benzoate, C20H32NO+·C7H5O− (II), trihexyphenidylium 4-bromo­benzoate, C20H32NO+·C7H4BrO2− (III), and trihexyphenidylium thio­phene-2-carboxyl­ate hemihydrate, 2C20H32NO+·2C5H3O2S−·H2O (IV), con­ducted at 90 K are described. Structures I, II, and III are solvent free with one cation–anion pair per asymmetric unit, while IV crystallizes as a hemihydrate, having two cation–anion pairs and one water of crystallization in its asymmetric unit. Structures I and III exhibit configurational disorder of the cation. Structure IV also exhibits disorder, but only of the thio­phene-2-carboxyl­ate anions. Structure II is a non-merohedric twin by a twofold rotation about [403]. The main supra­molecular motifs in I, II, and III are similar R22(10) rings between cation–anion pairs, although their packing within the crystals is distinct. As a consequence of having two cation–anion pairs and a water mol­ecule in its asymmetric unit, the packing in IV is by far the most complex of the four structures, its hydrogen-bonding patterns being quite different from I, II, or III. In all the crystals studied, N—H⋯O, O—H⋯O, and C—H⋯O inter­actions are observed, plus C—H⋯Br close contacts for III.

Item Type: Article
Uncontrolled Keywords: trihexyphenidyl, trihexyphenidylium cation, crystal structure, disorder, twinning, non-merohedry, hydrogen bonding
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: C Swapna Library Assistant
Date Deposited: 01 Aug 2023 09:04
Last Modified: 01 Aug 2023 09:04
URI: http://eprints.uni-mysore.ac.in/id/eprint/17674

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