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A new class of substituted 1,2,4-triazolo-1,3,4-thiadiazepines

, : A new class of substituted 1,2,4-triazolo-1,3,4-thiadiazepines. Acta Crystallographica. Section C, Crystal Structure Communications 50: 1608-1612

A series of 3-aryloxymethyl-(5-nitro-2-furyl)-6-phenyl-1,2,4- triazolo[3,4-b][1,3,4]thiadiazepine compounds have been synthesized recently by a new route. Reported here are the structures of two such compounds with para-substituted aryloxymethyl groups: one has a chloro group, 3-(4-chlorophenyl-oxymethyl)-8-(5-nitro-2-furyl)-6-phenyl-1,2,4- triazolo[3,4-b][1,3,4]thiadiazepine, C22H14C1N5O4S, TD1, and the other a methyl group, 3-(p-tolyloxy-methyl)-8-(5-nitro-2-furyl)-6-phenyl-1,2,4- triazolo-[3,4-b][1,3,4]thiadiazepine, C23H17N5O4S, TD7. The nitrofuryl and phenyl groups on the thiadiazepine ring are each found to adopt a similar conformation in the two structures, whereas the aryloxymethyl substituents on the triazole rings are conformationally different from each other. Each thiadiazepine ring adopts a boat conformation with the S atom at the apex. The interplanar angle between the triazole ring and the thiadiazepine ring is 30 degrees for both compounds. The conformation of the aryloxy-methyl group is dependent on the intermolecular interactions that arise as a result of the polarity of the para substituent. The Cl group in TD1 is involved in a C-Cl...O non-bonded interaction with a Cl...O distance of 3.100 (3) A and a C-Cl...O angle of 138.4 (1) degree. TD7 has a stacking interaction involving the nitrofuryl groups.


PMID: 7986428

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