Two-dimensional hydrogen-bonded networks in two novel glycoluril derivatives

Abstract

Two new glycoluril derivatives, namely diethyl 6-ethyl-1,4-dioxo-1,2,2a,3,4,6,7,7b-octahydro-5H-2,3,4a,6,7a-pentaazacyclopenta[cd]indene-2a,7b-dicarboxylate, C(14)H(21)N(5)O(6), (I), and 6-ethyl-2a,7b-diphenyl-1,2,2a,3,4,6,7,7b-octahydro-5H-2,3,4a,6,7a-pentaazacyclopenta[cd]indene-1,4-dione, C(20)H(21)N(5)O(2), (II), both bearing two free syn-urea NH groups and two ureidyl C=O groups, assemble the same one-dimensional chains in the solid state running parallel to the [010] direction via N-H...O hydrogen bonds. Furthermore, the chains of (I) are linked together into two-dimensional networks via C-H...O hydrogen bonds.

Diethyl 2,6-(2,4-dichlorophenyl)-4,8-dioxo-2,3,6,7-tetrahydro-1H,5H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-8b,8c-dicarboxylate

“…For the preparation of the title compound, see: Li et al (2006). For general background to glycoluril and its derivatives, see: Freeman et al (1981); Rebek (2005); Rowan et al (1999); Wu et al (2002); Cao et al (2008).…”

Novel Molecular Clip: Synthesis, Structure and Encapsulation of Small Solvent Molecule in the Crystal State

“…The geometrical features of this new molecular clip are similar to those reported previously. 18,28,29,31 For example, the =O…O= distance is 5.44 Å.…”

“…19 As part of our interest in the crystal engineering using the glycoluril skeleton as a building block, 20,21 we designed a number of fascinating molecular clips. 23,24,31,32 Furthermore, we obtained structural details for a wide variety of compounds by X-ray crystallography. We considered that glycoluril derivatives might be good building blocks for studies of crystal engineering because of their potential to engage in H-bonding and π-π interactions.…”