Synthesis and Crystal Structure of 5-[2-(6-bromonaphthalenyloxymethyl)]-3-(4-morpholinomethyl)-1,3,4-oxadiazole-2(3<Emphasis Type="Italic">H</Emphasis>)-thione |
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Authors: | Jerry P Jasinski Ray J Butcher Anil N Mayekar H S Yathirajan B Narayana B K Sarojini |
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Institution: | (1) Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA;(2) Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA;(3) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore, 570 006, India;(4) Department of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India;(5) Department of Chemistry, P.A. College of Engineering, Mangalore, 574 153, India |
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Abstract: | Abstract 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) ?, α = 92.779(3)°, β = 130.575(3)°, γ = 107.868(4)°, 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)°, respectively. The planar naphthyl ring is twisted 52.2(5)° 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 π–π 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···Br short-range interactions and Cg π–π stacking interactions on these
angles which therefore play a role in stabilizing crystal packing.
Graphical Abstract Crystal structure of 5-{(6-bromonaphthalen-2-yl)oxy]methyl}-3-(morpholin-4-ylmethyl)-1,3,4-oxadiazole-2(3H)-thione, C18H18BrN3O3S, is reported and its geometric and packing parameters described and compared to a MOPAC computational calculation.
Electronic supplementary material The online version of this article (doi:) contains supplementary material, which is available to authorized users. |
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Keywords: | Naphthyl Oxadiazol Morpholine π – π stacking interactions MOPAC |
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