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Two new glycoluril derivatives, namely 6-phenyl-1,4-dioxo-2,2a,3,4,6,7-hexahydro-1H,5H-2,3,4a,6,7a-pentaazacyclopenta[cd]indene-2a,7b-dicarboxylate (1), and diethyl 6-(2,4-dichorophenyl)-1,4-dioxo-2,2a,3,4,6,7-hexahydro-1H,5H-2,3,4a,6,7a-pentaazacyclopenta[cd]indene-2a,7b-dicarboxylate (2) have been synthesized and structurally determined by X-ray diffraction analysis. Compound 1 is, monoclinic, space group C2/c, with a = 20.0784(7), b = 9.0316(3), c = 23.0980(8) A, β = 98.3930(10), V = 4143.7(2) A3, with Z = 8 for d calc = 1.338 Mg/m3. The analog 2 is, Triclinic, space group P-1, with a = 8.9353(18), b = 10.466(2), c = 14.679(3) A, β = 73.60(3), V = 1268.1(4) A3, with Z = 2 for d calc = 1.533 Mg/m3. X-ray analysis reveals that both glycoluril derivatives bearing two free syn-urea NH groups and two ureidyl C=O, assemble the same one-dimensional chains in the solid-state running parallel to the [110], [1–10] and [010] directions via N–H···O hydrogen bonds. Two new glycoluril derivatives, namely 6-phenyl-1,4-dioxo-2,2a,3,4,6,7-hexahydro-1H,5H-2,3,4a,6,7a-pentaazacyclopenta[cd]indene-2a,7b-dicarboxylate (1), and diethyl 6-(2,4-dichorophenyl)-1,4-dioxo-2,2a,3,4,6,7-hexahydro-1H,5H-2,3,4a,6,7a-pentaazacyclopenta[cd]indene-2a,7b-dicarboxylate (2), both bearing two free syn-urea NH groups and two ureidyl C=O, assemble the same one-dimensional chains in the solid-state running parallel to the [110], [1–10] and [010] directions via R 2 2 (8) N–H···O hydrogen bonds.

The title compound, C15H12F3N5O3, is a by-product isolated from the preparation of di-2-pyridiylglycoluril. The mol­ecule contains two classical intra­molecular N—H⋯N and N—H⋯O hydrogen bonds, and its crystal structure is stabilized mostly by inter­molecular N—H⋯O hydrogen bonds.

In the structure of the title compound, C33H26N2O4, two phthalimide units are symmetrically linked by a bis­(3,5-dimethyl­phen­yl)methane bridge. The methyl­ene C atom of this bridge lies on a twofold rotation axis. The dihedral angle between the planes of the two central benzene rings is 61.4 (4)°. The terminal isoindole group is approximately planar, with an r.m.s. deviation of atoms from the mean plane of 0.012 A and a dihedral angle of 75.3 (14)° with the attached benzene ring. An extensive network of C—H⋯O hydrogen bonds stabilizes the crystal structure.

The title compound, C14H18N4O8, is a glycoluril derivative, composed of two five-membered rings in envelope conformations and two six-membered rings in chair conformations. In the crystal structure, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional network. One methyl group and the H atoms on the adjacent C atom are disordered over two positions; the site-occupancy factors are ca 0.62 and 0.38.