3-(6-Methyl-2-pyridyl)-2-phenoxy-3,4-dihydro-1,3,2-benzoxazaphosphirine 2-oxide

Abstract

In the title compound, C19H17N2O3P, the six-membered 1,3,2-oxaza­phospho­rine ring adopts a twist-boat conformation with the phosphoryl O atom in an equatorial position. The P=O(oxide) bond length is 1.457 (1) Å and the average value of the P—O distances is 1.588 Å. The crystal structure is stabilized by C—H⋯O and C—H⋯π inter­actions.

3-(6-Methyl-2-pyridyl)-2-phenyl-3,4-dihydro-1,3,2-benzoxazaphosphinine 2-oxide

“…1), the oxazaphosphinine ring exhibits a boat conformation where atoms C6/C7/C12/O4 are almost coplanar and atoms P1 and N2 displaced in the same direction by 0.936 (1) and 0.936 (1) Å, respectively. The single and double bond lengths of P and O atoms are in good agreement with the similar structures reported previously (Brzozowski et al, 1990;Angelov et al, 2002;Kant et al, 2009). The P-N bond length, 1.6702 (14) Å, and the P-N-C bond angle, 120.30 (13)°, are comparable with the related structure of [1,3,2]-oxazaphosphorine-6-sulfide (Radha Krishna et al, 2007), but the bond distance shows relatively higher value when compared with the similar benzoxazaphosphorine structures (Yang et al, 1988;Subramanian et al, 1989;Selladurai & Subramanian, 1990;Selladurai et al, 1991).…”

“…For the biological activity of organophosphorus compounds, see: Hoagland (1988); Smith (1983); Molodykh et al (1990). For P-O and P O bond lengths in related structures, see: Brzozowski et al (1990); Angelov et al (2002); Kant et al (2009). For P-N bond lengths in related structures, see: Radha Krishna et al (2007); Yang et al (1988); Subramanian et al (1989); Selladurai & Subramanian (1990); Selladurai et al (1991).…”

6-Bromo-2-(4-nitrophenoxy)-3-(1-phenylethyl)-3,4-dihydro-1,3,2-benzoxazaphosphinine 2-oxide

“…The nitrophenoxy and phenylethyl rings are at axially and equatorially orientated with dihedral angles of 27.2 (1)° and 71.0 (1)° to the mean plane of heterocyclic ring. The P=O(2) distance of 1.456 (2)Å is in good agreement with the values in related structures (Kant et al, 2009;Krishnaiah et al, 2007)…”

“…For background information on organophosphorus heterocyclic compounds containing O and N in the six membered ring, see: Srinivasulu et al (2008); Hill (1975); Reddy et al (2004); Prasad et al (2006); Sosnovsky & Paul (1983). For related structures, see: Krishnaiah et al (2007); Pattabhi (1975); Radha Krishna et al (2007); Symes et al (1988); Hay & Mackay (1979); Kant et al (2009); Selladurai et al (1989).…”