Abstract
The benzo-pyran ring of the title com-pound, C16H11ClN2O2, is planar [maximum deviation = 0.079 (2) Å] and is almost perpendicular to the chloro-phenyl ring [dihedral angle = 86.85 (6)°]. In the crystal, N-H⋯O, O-H⋯N, C-H⋯O and C-H⋯Cl hydrogen bonds form inter- and intra-molecular inter-actions. The DFT/B3LYP/6-311G(d,p) method was used to determine the HOMO-LUMO energy levels. The mol-ecular electrostatic potential surfaces were investigated by Hirshfeld surface analysis and two-dimensional fingerprint plots were used to analyse the inter-molecular inter-actions in the mol-ecule.
Highlights
The benzopyran ring of the title compound, C16H11ClN2O2, is planar [maximum deviation = 0.079 (2) A ] and is almost perpendicular to the chlorophenyl ring [dihedral angle = 86.85 (6)]
The molecular electrostatic potential surfaces were investigated by Hirshfeld surface analysis and two-dimensional fingerprint plots were used to analyse the intermolecular interactions in the molecule
Numerous naturally-occurring compounds containing pyrans and benzopyrans show fascinating therapeutic activities, which include their use as antimicrobial (Khafagy et al, 2002), antiviral (Smith et al, 1998; Martınez-Grau & Marco, 1997), mutagenicity (Hiramoto et al, 1997), antiproliferative (Dell & Smith, 1993), antitumour (Mohr et al, 1975), antituberculosis (Ferreira et al, 2010), anti-HIV (He et al, 2011), antifungal (Schiller et al, 2010), antidiabetic (Bisht et al, 2011) and antiinflammatory agents (Wang et al, 1996, 2005)
Summary
Pyran is an oxygen-containing heterocyclic group that exhibits various pharmacological activities. Numerous naturally-occurring compounds containing pyrans and benzopyrans show fascinating therapeutic activities, which include their use as antimicrobial (Khafagy et al, 2002), antiviral (Smith et al, 1998; Martınez-Grau & Marco, 1997), mutagenicity (Hiramoto et al, 1997), antiproliferative (Dell & Smith, 1993), antitumour (Mohr et al, 1975), antituberculosis (Ferreira et al, 2010), anti-HIV (He et al, 2011), antifungal (Schiller et al, 2010), antidiabetic (Bisht et al, 2011) and antiinflammatory agents (Wang et al, 1996, 2005) They are used in cancer chemotherapy (Anderson et al, 2005), in sex pheromone therapy (Bianchi & Tava, 1987) to control central nervous system activities (Eiden & Denk, 1991) and as calcium-channel antagonists (Shahrisa et al, 2011), These attributes have prompted considerable research work in the synthetic field and interest in their structures, reactivities and biological properties. The sum of the bond angles around atom N1 of the pyran ring is in accordance with the sp2-hybridization state (360; Beddoes et al, 1986)
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