1,3-Dicyclohexylimidazolidine-2,4,5-trione

Abstract

The title compound, C15H22N2O3, has been isolated as a by-product of an oxidative cleavage of the C—C bond linking two five-membered rings of 1,3-dicyclo­hexyl-5-(3-oxo-2,3-dihydro­benzofuran-2-yl)imidazolidine-2,4-dione. Individual mol­ecular units are engaged in weak C=O⋯C=O inter­actions [O⋯C = 2.814 (10) and 2.871 (11) Å], leading to the formation of supra­molecular chains which close pack, mediated by van der Waals contacts, in the bc plane.

1,3-Dicyclohexylimidazolidine-2,4,5-trione: a second polymorph

“…The two cyclohexyl substituent groups appear exhibiting the chair typical conformation and their medium planes subtend slightly different angles with the aforementioned central plane, being one almost perpendicular [88.73 (5)°] and the other of 74.15 (6)°. We note that the observed angles for these two planes are larger than those registered for polymorph I in which the analogous values are ca 81 and 87° (Talhi et al, 2011). Remarkably the four possible N-C-C-C groups involving three adjacent carbon atoms of the cyclohexyl moieties are also very near the planarity [largest deviation of 0.019 1…”

“…Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT-Plus (Bruker, 2005); data reduction: SAINT-Plus (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008). In a previous publication (Talhi et al, 2011) we described the crystal structure (polymorph I) of 1,3-dicyclohexylparabanic acid (see chemical diagram and Figure 1) obtained as a by-product of the oxidative cleavage of the C2′-C5 single bond of 1,3-dicyclohexyl-(3-oxo-2,3-dihydrobenzofuran-2-yl)imidazolidine-2,4-dione, using catalytic I 2 /DMSO system at 463 K. Following our interest on the structural features of compounds having biological activity Loughzail et al 2011;Talhi et al, 2011), particularly in our quest for novel polymorphic forms of pharmaceutic products, we wish to report the structure of a second crystalline polymorph of the title compound (polymorph II) obtained when applying a different crystallization procedure from that previously reported by us: while polymorph I was obtained by slow evaporation of an ethanolic solution at room temperature, polymorph II was obtained instead by cooling overnight the same solution at 253 K.…”

“…For the structure of the orthorhombic polymorph and further background information to the study, see: Talhi et al (2011). For general background on crystallographic studies by our research group of related compounds having biological activity, see: Fernandes et al (2011); Loughzail et al (2011).…”

“…The title compound was prepared following the procedure described previously (Talhi et al, 2011), except for the crystallization process in which the raw compound was dissolved in ethanol and crystallized at 253 K overnight.…”

“…Herein, we report the crystal structure of a second polymorph, which was obtained by crystallization from an ethanol solution at 253 K, instead of slow evaporation of the same solvent at room temperature. While the first polymorph [Talhi et al (2011). Acta Cryst.…”