D. Tranqui et al., CRYSTAL-STRUCTURE STUDY OF (E)-3-(4-NITROBENZYLOXYIMINO)HEXAHYDROAZEPIN-2-ONE USING SYNCHROTRON-RADIATION, Journal of synchrotron radiation, 4, 1997, pp. 78-82
NOHA, 3-(4-nitrobenzyloxyimino)hexahydroazepin-2-one, is a potent anti
convulsive agent. It occurs in two stereoisomers. the Z and E forms. (
E)-NOHA is about 1.5 times more active than (Z)-NOHA. While accurate s
tructural data are available for (Z)-NOHA, those for the E form hare r
emained, until recently, highly speculative due to the lack of single
crystals of suitable size for X-ray analysis and to the instability of
the E isomer under radiation exposure. For structure-activity correla
tion purposes, efforts have been made to solve the crystal structure o
f the E isomer. Data collection from tiny needle crystals has been per
formed using synchrotron radiation. An initial molecular-packing model
of this compound was obtained by energy-based and X-ray data modellin
g and successfully refined by molecular-dynamics methods: space group
P2(1)/c, a = 6.225 (5), b = 17.885 (5), c = 12.157(5)Angstrom, beta =
92.35(5)degrees, R factor = 3.5% for 343 reflections. In this contribu
tion the crystal and molecular structure of (E)-NOHA is reported and t
he role of the hydrogen bond acting as the driving force in the interm
olecular assembly in the (E)-NOHA crystal is highlighted.