Crystal structure of 13-(2-methoxyphenyl)-3,4-dihydro-2H-indazolo[1,2-b]phthalazine-1,6,11(13H)-trione

Abstract

In the title compound, C22H18N2O4, the three fused rings of the pyrazolo­phthalazine moiety are coplanar (r.m.s. deviation = 0.027 Å). The cyclo­hexene ring fused to the pyrazolidine ring, so forming the indazolophthalazine unit, has a half-chair conformation. The benzene ring is almost normal to the mean plane of the pyrazolo­phthalazine moiety, with a dihedral angle of 87.21 (6)° between their planes. In the crystal, mol­ecules are linked by pairs of C—H⋯O hydrogen bonds forming inversion dimers. The dimers are linked via C—H⋯π inter­actions, forming slabs parallel to (100). Between the slabs there are weak π–π inter­actions [shortest inter-centroid distance = 3.6664 (9) Å], leading to the formation of a three-dimensional structure.

Crystal structure of 13-phenyl-2,3,4,13-tetrahydro-1H-indazolo[1,2-b]phthalazine-1,6,11-trione

“…For application of phthalazine derivatives see: Mosaddegh & Hassankhani (2011); Hasaninejed et al (2012); Keshipour et al (2012). For the synthesis of this class of compounds, see: Carling et al (2004); Cashman & Ghirmai (2009); Hall et al (1992Hall et al ( , 2001; Bouraiou et al (2015); Nomoto et al (1990). For the synthesis of the title compound, see: Bouraiou et al (2015); Khurana & Magoo (2009); Nagarapu et al (2009 Table 1 Hydrogen-bond geometry (Å , ).…”

“…Therefore, a number of synthetic methods have been developed in recent years to uncover a variety of new reagents for the synthesis of phthalazine derivatives (Mosaddegh & Hassankhani, 2011;Hasaninejed et al, 2012;Keshipour et al, 2012). In previous work, we have reported the synthesis and structure heterocyclic compounds bearing a phthalazine unit (Bouraiou et al, 2015). Herein, we describe the synthesis and crystal structure of the title indazolo phthalazine-trione derivative, resulting from the reaction of phthalhydrazide, cyclohexa-1,3-dione and benzaldehyde in the presence of catalytic amounts of sulfuric acid.…”

“…The title compound was synthesized in accordance with established methods (Khurana & Magoo, 2009;Bouraiou et al, 2015). Spectroscopic results and physical properties are in agreement with literature reports (Nagarapu et al, 2009 192.6, 156.1, 154.3, 152.3, 136.4, 134.6, 133.6, 129.1, 129.0, 128.7, 128.0, 127.8, 127.2, 119.7, 65.0, 37.0, 24.6, 22.3.…”