r-2,c-6-Bis(2-chlorophenyl)-t-3,t-5-dimethyl-1-nitrosopiperidin-4-one oxime

Abstract

In the title compound, C19H19Cl2N3O2, the piperidine ring adopts a distorted boat conformation. In the solid state, the mol­ecules exist as O—H⋯N‐hydrogen‐bonded centrosymmetric dimers.

t-3-Methyl-1-nitroso-r-2,c-6-diphenylpiperidin-4-one oxime monohydrate

“…For comparison, the matrix of the r.m.s. deviations for the superposition of the non-H atoms common to the structures of (I), (II), r-2,c-6-bis(2-chlorophenyl)-t-3,t-5-dimethyl-1-nitrosopiperidin-4-one oxime, (III) (Hema, Parthasarathi, Ravikumar, Sridhar, Pandiarajan & Muthukumaran, 2005), and r-2,c-6-bis(4-chlorophenyl)-t-3,t-5-dimethyl-1-nitrosopiperidin-4-one oxime, (IV) is given in Table 1, with the superposition shown in Fig. 2.…”

Synthesis and structural study of 3t-isopropyl-2r,6c-diphenyl-4-oxopiperidinium nitrate and N-benzoyl-3t-isopropyl-2r,6c-diphenylpiperidin-4-one oxime

“…Though N-nitroso-3t-methyl-2r,6c-diphenylpiperidine-4-one oxime (6) has been shown [12] to adopt boat conformation 6B2 with NO group anti to C-2 recently [16], the corresponding ketone 7 has been shown to adopt boat conformation 7B1 with NO group Symmetry transformations used to generate equivalent atoms: #1 Àx + 2,Ày + 1, z À 1/2 #2 x, y, z À 1. syn to C-2, in the solid state. Thus, it seems that in the case of Nnitroso compounds piperidin-4-ones and their oximes may adopt different conformations in the solid state.…”

“…The crystal structure of 3t-isopropyl-2r,6c-diphenylpiperidin-4-one (1) has been reported [9]. Crystal structures of N-nitroso-2r,6c-diarylpiperidin-4-one oximes have been reported [10][11][12].…”

r-2,c-6-Bis(4-chlorophenyl)-t-3,t-5-dimethyl-1-nitrosopiperidin-4-one oxime

“…These N-nitroso compounds are often found in a variety of environmental samples. Even though the unsubstituted N-nitrosopiperidines are potential carcinogens, when an alkyl group is substituted at the position C2, it reduces the carcinogenicity (Hema et al, 2005). Most of the piperidine precursors are known to exist in chair conformations (Sekar & Parthasarathy, 1993).…”

“…Compound (I) is analogous to a related structure, r-2,c-6bis(2-chlorophenyl)-t-3,t-5-dimethyl-1-nitrosopiperidin-4-one oxime, (II) (Hema et al, 2005), except for the substitution of Cl atoms at the para-positions of the two benzene rings in (I) instead of the ortho-positions in (II). Superposition of non-H atoms common to the structures of (I) and (II) gives an r.m.s.…”