1-Methyl-3-(naphthalen-1-yl)-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile

Abstract

In the title compound, C22H18N2O2, the pyran ring of the chromene unit is fused with an isoxazole ring, which adopts an N-envelope conformation with the N atom lying 1.3291 (14) Å from the mean plane of the remaining ring atoms [maximum deviation = 0.341 (2) Å]. The dihedral angle between the isoxazole and chromene units is 43.74 (8)° and that between the iosxazole ring and the naphthalene ring system is 58.82 (8)°. In the crystal, the molecules are linked by weak C—H⋯π inter­actions.

3-(2-Methylphenyl)-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbonitrile

“…The isoxazole ring also forms a dihedral angle of 74.6 (2)° with the the benzene ring (C11-C16). The geometric parameters of the title molecule agree well with those reported for closely related structures (Gangadharan et al, 2011;Swaminathan et al, 2011).…”

“…For the biological importance of 4H-chromene derivatives, see: Cai (2007Cai ( , 2008; Cai et al (2006); Gabor (1988); Brooks (1998); Valenti et al (1993); Hyana & Saimoto (1987); Tang et al (2007). For related structures, see: Gangadharan et al (2011); Swaminathan et al (2011). Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).…”

Crystal structures of methyl 3-(4-isopropylphenyl)-1-methyl-1,2,3,3a,4,9b-hexahydrothiochromeno[4,3-b]pyrrole-3a-carboxylate, methyl 1-methyl-3-(o-tolyl)-1,2,3,3a,4,9b-hexahydrothiochromeno[4,3-b]pyrrole-3a-carboxylate and methyl 1-methyl-3-(o-tolyl)-3,3a,4,9b-tetrahydro-1H-thiochromeno[4,3-c]isoxazole-3a-carboxylate

“…The dihedral angles between the mean plane of the isoxazole ring and the thiopyran ring mean plane and the benzene ring are 60.34 (12) and 61.30 14, respectively. The geometric parameters of molecule (III) agree well with those reported for (I) and (II), and a closely related structure, 1-methyl-3-(naphthalen-1-yl)-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile (Gangadharan et al, 2011).…”

1-Methyl-3-p-tolyl-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile

“…The geometric parameters of the title compound agree well with reported structure (Gangadharan et al, 2011).…”

“…For a related structure, see: Gangadharan et al (2011). For puckering parameters, see: Cremer & Pople (1975).…”