Open AccessConformations of three heterocyclic perhydropyrrolobenzofurans and polymeric assembly via co‐operative intermolecular C—H⋯O hydrogen bonds
Author(s) -
Yathirajan H. S.,
Narasegowda R. S.,
Lynch D. E.,
Narasimhamurthy T.,
Rathore R. S.
Publication year - 2006
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s010827010601119x
Subject(s) - intramolecular force , chemistry , pyrrolidine , intermolecular force , pyrrole , ring (chemistry) , hydrogen bond , substituent , molecule , stereochemistry , crystallography , organic chemistry
In 1‐cyclohexyl‐6,6,8a‐trimethyl‐3a,6,7,8a‐tetrahydro‐1 H ‐1‐benzofuro[2,3‐ b ]pyrrole‐2,4(3 H ,5 H )‐dione, C 19 H 27 NO 3 , (I), and the isomorphous compounds 6,6,8a‐trimethyl‐1‐phenyl‐3a,6,7,8a‐tetrahydro‐1 H ‐1‐benzofuro[2,3‐ b ]pyrrole‐2,4(3 H ,5 H )‐dione, C 19 H 21 NO 3 , (II), and 6,6,8a‐trimethyl‐1‐(3‐pyridyl)‐3a,6,7,8a‐tetrahydro‐1 H ‐1‐benzofuro[2,3‐ b ]pyrrole‐2,4(3 H ,5 H )‐dione, C 18 H 20 N 2 O 3 , (III), the tetrahydrobenzo–dihydrofuro–pyrrolidine ring systems are folded at the cis junction of the five‐membered rings, giving rise to a non‐planar shape of the tricyclic cores. The dihydrofuran and pyrrolidine rings in (I) are puckered and adopt an envelope conformation. The cyclohexene rings adopt a half‐chair conformation in all the molecules, while the substituent N ‐cyclohexyl ring in (I) assumes a chair form. Short intramolecular C—H⋯O contacts form S (5) and S (6) motifs. The isomorphous compounds (II) and (III) are effectively isostructural, and aggregate into chains via intermolecular C—H⋯O hydrogen bonds.