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Four related benzazepine derivatives in a reaction pathway leading to a benzazepine carboxylic acid: hydrogen‐bonded assembly in zero, one, two and three dimensions
Author(s) -
Guerrero Sergio A.,
Sanabría Carlos M.,
Palma Alirio,
Cobo Justo,
Glidewell Christopher
Publication year - 2014
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229614006007
Subject(s) - benzazepine , chemistry , mathematics , stereochemistry
(2 R *,4 S *)‐Methyl 2,3,4,5‐tetrahydro‐1,4‐epoxy‐1 H ‐benz[ b ]azepine‐2‐carboxylate, C 12 H 13 NO 3 , (I), and its reduction product (2 R *,4 S *)‐methyl 4‐hydroxy‐2,3,4,5‐tetrahydro‐1 H ‐benz[ b ]azepine‐2‐carboxylate, C 12 H 15 NO 3 , (II), both crystallize as single enantiomers in the space group P 2 1 2 1 2 1 , while the hydrolysis product (2 RS ,4 SR )‐4‐hydroxy‐2,3,4,5‐tetrahydro‐1 H ‐benz[ b ]azepine‐2‐carboxylic acid, C 11 H 13 NO 3 , (III), and the lactone (2 RS ,5 SR )‐8‐(trifluoromethoxy)‐5,6‐dihydro‐1 H ‐2,5‐methanobenz[ e ][1,4]oxazocin‐3(2 H )‐one, C 12 H 10 F 3 NO 3 , (IV), both crystallize as racemic mixtures in the space group P 2 1 / c . The molecules of compound (IV) are linked into centrosymmetric R 2 2 (10) dimers by N—H...O hydrogen bonds, and those of compound (I) are linked into chains by C—H...π(arene) hydrogen bonds. A combination of O—H...O and O—H...N hydrogen bonds links the molecules of compound (III) into sheets containing equal numbers of R 4 4 (14) and R 4 4 (26) rings, and a combination of C—H...π(arene) hydrogen bonds and three‐centre O—H...(N,O) hydrogen bonds links the molecules of compound (II) into a three‐dimensional framework structure. Comparisons are made with some related compounds.