Structural studies of organoboron compounds. LIII. N,N-Diethylhydroxylamine-(O-B)1,7-dimethyl-3,5-diphenyl-2,4,6-trioxa-7-aza-1-azonia-3-bora-5- boratabicyclo[3.3.0]octane

Reaction of the condensation product of N,N′-dimethyl-N,N′-dihydroxymethanediamine and phenylboronic acid with N,N-diethylhydroxylamine gives N,N-diethylhydroxylamine(O-B)1,7-dimethyl-3,5-diphenyl-2,4,6-trioxa-7-aza-1-azonia-3-bora-5-boratabicyclo[3.3.0]octane [3-(2-ethyl-1-oxa-2-azoniabutyl)-1,7-dimethyl-3,5-diphenyl-2,4,6-trioxa-7-aza-1-azonia-3,5-diboratabicyclo[3.3.0]octane, 3] in high yield. Crystals of 3 are orthorhombic, a = 11.8132(11), b = 15.4768(11), c = 11.7325(16) Å, Z = 4, space group P2 1 2 1 2 1 . The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R = 0.039 and R w  = 0.044 for 1729 reflections with I ≥ 2σ(I). The title compound is the second example of this recently characterized class of O-B coordinated hydroxylamine complexes, stabilized by an intramolecular [Formula: see text] hydrogen bond [Formula: see text]. Bond lengths about boron are: B—O(N) = 1.482(4)–1.526(4), B—O(B) = 1.412(4) and 1.420(4), B—N = 1.712(4), B—C = 1.591(5) and 1.602(5) Å.