Synthesis and Crystal Structure of 5-2-(6-bromonaphthalenyloxymethyl)]3-(4-morpholinomethyl)-1,3,4-oxadi azole-2(3H)-thione

Jasinski, Jerry P. and Butcher, Ray J. and Mayekar, Anil N. and Yathirajan, H. S. and Narayana, B. and Sarojini, B. K. (2009) Synthesis and Crystal Structure of 5-2-(6-bromonaphthalenyloxymethyl)]3-(4-morpholinomethyl)-1,3,4-oxadi azole-2(3H)-thione. JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 39 (10). pp. 761-765. ISSN 1572-8854

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The title compound, C18H18BrN3O3S, a derivative of 1,3,4-oxadiazole, crystallizes in the triclinic space group P-1 with unit cell parameters a = 6.8731(3), b = 8.9994(4), c = 15.7099(6) angstrom, alpha = 92.779(3)degrees, beta = 130.575(3)degrees, gamma = 107.868(4)degrees, Z = 2. The dihedral angle between the mean planes of the planar naphthyl and morpholine (chair) rings with the planar oxadiazol ring is 50.1(8) and 76.8(6)degrees, respectively. The planar naphthyl ring is twisted 52.2(5)degrees with the mean plane of the morpholine ring. A group of four intermolecular close contacts are observed between a bromine atom and hydrogen atoms from the closely packed naphthyl, morpholine and oxy-methyl groups in the unit cell. These molecular interactions in concert with an additional series of pi-pi stacking interactions that occur between the center of gravity of the two 6-membered rings of the naphthalene group influence the twist angles of each of these three groups. A MOPAC AM1 calculation of the conformation energy of the crystal structure 226.0128(9) kcal] compared to that of the minimum energy structure after geometry optimization 29.9744(1) kcal] reveals a significantly reduced value. The twist angles of the three groups above also change after the AM1 calculation giving support to the influence of both intermolecular C-H center dot center dot center dot Br short-range interactions and Cg pi-pi stacking interactions on these angles which therefore play a role in stabilizing crystal packing.

Item Type: Article
Uncontrolled Keywords: Naphthyl; Oxadiazol; Morpholine; pi-pi stacking interactions; MOPAC
Subjects: C Chemical Science > Chemistry
Divisions: Department of > Chemistry
Depositing User: Users 19 not found.
Date Deposited: 17 Aug 2019 10:41
Last Modified: 17 Aug 2019 10:41

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