2-[(Cyclohex-3-en-1-ylmethoxy)methyl]-6-phenyl-1,2,4-triazine-3,5(2H,4H)-dione

Abstract

In the title 1,2,4-triazine derivative, C17H19N3O3, the heterocyclic ring is planar (r.m.s. deviation = 0.040 Å) and effectively coplanar with the adjacent phenyl ring [dihedral angle = 4.5 (2)°] but almost perpendicular to the (cyclohex-3-en-1-ylmethoxy)methyl residue [N—N—C—O torsion angle = 71.6 (5)°], so that the molecule has an `L' shape. Supramolecular chains along [001] are formed in the crystal via N—H...O hydrogen bonds where the acceptor O atom is the ether O atom. The adjacent carbonyl O atom forms a complementary C—H...O contact resulting in the formation of a seven-membered {...HNCO...HCO} heterosynthon; the second carbonyl O atom forms an intramolecular C—H...O contact. Chains are connected into a supramolecular layer in the ac plane by π–π interactions [ring centroid–centroid distance = 3.488 (3) Å]. The central atom in the –CH2CH2C(H)= residue of the cyclohexene ring is disordered over two sites, with the major component having a site-occupancy factor of 0.51 (2).