Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supra­moleular assembly mediated by C—H⋯π and C—Br⋯π inter­actions

Girisha, M. and Sagar, B. K. and Yathirajan, H. S. and Rathore, Ravindranath S. and Glidewell, Christopher (2017) Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supra­moleular assembly mediated by C—H⋯π and C—Br⋯π inter­actions. Acta Crystallographica Section C, 73 (2). pp. 115-120. ISSN 2053-2296

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Abstract

It has been observed that when electron-rich naphthyl rings are present in chalcones they can participate in π–π stacking inter­actions, and this can play an important role in orientating inhibitors within the active sites of enzymes, while chalcones containing heterocyclic substituents additionally exhibit fungistatic and fungicidal properties. With these considerations in mind, three new chalcones containing 2-naphthyl substituents were prepared. 3-(4-Fluoro­phen­yl)-1-(naphthalen-2-yl)prop-2-en-1-one, C19H13FO, (I), crystallizes with Z′ = 2 in the space group P[\overline{1}] and the four mol­ecules in the unit cell adopt an arrangement which resembles that in the space group P21/a. Although 3-(4-bromo­phen­yl)-1-(naphthalen-2-yl)prop-2-en-1-one, C19H13BrO, (II), with Z′ = 1, is not iso­struc­tural with (I), the mol­ecules of (I) and (II) adopt very similar conformations. In 1-(naphthalen-2-yl)-3-(thio­phen-2-yl)prop-2-en-1-one, C17H12OS, (III), the thio­phene unit is disordered over two sets of atomic sites, with occupancies of 0.780 (3) and 0.220 (3), which are related by a near 180° rotation of the thio­phene unit about its exocyclic C—C bond. The mol­ecules of compound (I) are linked by three independent C—H⋯π(arene) hydrogen bonds to form centrosymmetric octa­molecular aggregates, whereas the mol­ecules of compound (II) are linked into mol­ecular ladders by a combination of C—H⋯π(arene) and C—Br⋯π(arene) inter­actions, and those of compound (III) are linked into centrosymmetric dimers by C—H⋯π(thio­phene) inter­actions.

Item Type:	Article
Uncontrolled Keywords:	chalcones, crystal structure, pseudosymmetry, disorder, molecular conformation, molecular aggregate, hydrogen bonding, C-Br...pi bonding, Claisen-Schmidt condensation reaction
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	C Swapna Library Assistant
Date Deposited:	02 Nov 2019 09:49
Last Modified:	02 Nov 2019 09:49
URI:	http://eprints.uni-mysore.ac.in/id/eprint/9775

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