title: A chalcone showing positional disorder, two related diarylcyclohexenones showing enantiomeric disorder and a related hydroxyterphenyl, all derived from simple carbonyl precursors.
abstract: Four compounds are reported, all of which lie along a versatile reaction pathway which leads from simple carbonyl compounds to terphenyls. (2E)-1-(2,4-Dichlorophenyl)-3- [4-(prop-1-en-2-yl)phenyl]prop-2-en-1-one, C18H14Cl2O, (I), prepared from 4-(prop-1-en-2-yl)benzaldehyde and 2,4-dichloroacetophenone, exhibits disorder over two sets of atomic sites having occupancies of 0.664 (6) and 0.336 (6). The related chalcone (2E)-3-(4-chlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one reacts with acetone to produce (5RS)-3-(4-chlorophenyl)-5-[4-(propan-2-yl)phenyl]cyclohex-2-en-1-one, C21H21ClO, (II), which exhibits enantiomeric disorder with occupancies at the reference site of 0.662 (4) and 0.338 (4) for the (5R) and (5S) forms; the same chalcone reacts with methyl 3-oxobutanoate to give methyl (1RS,6SR)-4-(4-chlorophenyl)-6-[4-(propan-2-yl)phenyl]-2-oxocyclohex-3-ene-1-carboxylate, C23H23ClO3, (III), where the reference site contains both (1R,6S) and (1S,6R) forms with occupancies of 0.923 (3) and 0.077 (3), respectively. Oxidation, using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, of ethyl (1RS,6SR)-6-(4-bromophenyl)-4-(4-fluorophenyl)-2-oxocyclohex-3-ene-1-carboxylate, prepared in a similar manner to (II) and (III), produces ethyl 4''-bromo-4-fluoro-5'-hydroxy-1,1':3',1''-terphenyl-4'-carboxylate, C21H16BrFO3, (IV), which crystallizes with Z' = 2 in the space group P-1. There are no significant intermolecular interactions in the structures of compounds (I) and (II), but for the major disorder component of compound (III), the molecules are linked into sheets by a combination of C-H...O and C-H...π(arene) hydrogen bonds. The two independent molecules of compound (IV) form two different centrosymmetric dimers, one built from inversion-related pairs of C-H...O hydrogen bonds and the other from inversion-related pairs of C-H...π(arene) hydrogen bonds. Comparisons are made with related compounds.
authors.affiliation: Department of Studies in Chemistry, Mangalore University, Mangalagangothri 574 199, India.
authors.forename: Vinutha V
authors.initials: VV
authors.lastname: Salian
authors.affiliation: Department of Studies in Chemistry, Mangalore University, Mangalagangothri 574 199, India.
authors.forename: Badiadka
authors.initials: B
authors.lastname: Narayana
authors.affiliation: Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.
authors.forename: Hemmige S
authors.initials: HS
authors.lastname: Yathirajan
authors.affiliation: Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
authors.forename: Mehmet
authors.initials: M
authors.lastname: Akkurt
authors.affiliation: Department of Physics, Faculty of Education, Dicle University, 21280 Diyarbakir, Turkey.
authors.forename: Ömer
authors.initials: Ö
authors.lastname: Çelik
authors.affiliation: Department of Physics, Faculty of Arts and Sciences, Sinop University, 57010 Sinop, Turkey.
authors.forename: Cem Cüneyt
authors.initials: CC
authors.lastname: Ersanlı
authors.affiliation: School of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland.
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry*; D002599:Chalcone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003512:Cyclohexanones / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D006860:Hydrogen Bonding; D015394:Molecular Structure; D011407:Propane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C000598534:1-(2,4-dichlorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one; C000602410:4-(4-chlorophenyl)-6-(4-(propan-2-yl)phenyl)-2-oxocyclohex-3-ene-1-carboxylate; C000602409:4-(prop-1-en-2-yl)benzaldehyde; D001547:Benzaldehydes; D003512:Cyclohexanones; D006843:Hydrocarbons, Chlorinated; D002599:Chalcone; D011407:Propane
keywords: chalcones; crystal structure; diarylcyclohexenones; enantiomeric disorder; hydrogen bonding; supramolecular aggregation; terphenyls