Abstract
The title compound, C16H18N2O3, is constructed about a central oxopyridazinyl ring (r.m.s. deviation = 0.0047 Å), which is connected to an ethyl-acetate group at the N atom closest to the carbonyl group, and benzyl and methyl groups second furthest and furthest from the carbonyl group, respectively. An approximately orthogonal relationship exists between the oxopyridazinyl ring and the best plane through the ethyl-acetate group [dihedral angle = 77.48 (3)°]; the latter lies to one side of the central plane [the Nr-Nr-Cm-Cc (r = ring, m = methyl-ene, c = carbon-yl) torsion angle being 104.34 (9)°]. In the crystal, both H atoms of the N-bound methyl-ene group form methyl-ene-C-H⋯O(ring carbon-yl) or N(pyridazin-yl) inter-actions, resulting in the formation of a supra-molecular tape along the a-axis direction. The tapes are assembled into a three-dimensional architecture by methyl- and phenyl-C-H⋯O(ring carbon-yl) and phenyl-C-H⋯O(ester carbon-yl) inter-actions. The analysis of the calculated Hirshfeld surface indicates the dominance of H⋯H contacts to the overall surface (i.e. 52.2%). Reflecting other identified points of contact between mol-ecules noted above, O⋯H/H⋯O (23.3%), C⋯H/H⋯C (14.7%) and N⋯H/H⋯N (6.6%) contacts also make significant contributions to the surface.
Highlights
The molecular structure of (I), Fig. 1, comprises a central oxopyridazinyl ring connected to an ethylacetate group at the N1 atom, a methyl group at the C2 position and a benzyl residue at the C3 atom
The benzyl ring forms a dihedral angle of 76.94 (3) with the central ring, indicating an approximately orthogonal relationship but, in this case, the benzyl ring is bisected by the pseudo mirror plane passing through the oxopyridazinyl ring
The intense blue and red regions corresponding to positive and negative electrostatic potentials on the Hirshfeld surfaces mapped over electrostatic potential in Fig. 4 represent the donors and acceptors of the above intermolecular interactions, respectively
Summary
Pyridazin-3(2H)-ones are pyridazine derivatives, being constructed about a six-membered ring which contains two adjacent nitrogen atoms, at positions one and two, and with a carbonyl group at position three. The interest in these nitrogen-rich heterocyclic derivatives arises from the fact that they exhibit a number of promising pharmacological and biological activities. Given the interest in this class of compound and the paucity in structural data (see Database survey), the crystal and molecular structures of the the title pyridazin-3(2H)-one derivative, (I), has. E75, 392–396 research communications been undertaken along with an analysis of the calculated Hirshfeld surface in order to gain further insight into the molecular packing. Symmetry codes: (i) Àx þ 2; Ày þ 1; Àz þ 1; (ii) Àx þ 1; Ày þ 1; Àz þ 1
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