2011
DOI: 10.1107/s1600536811016977
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(2E)-3-(3-Benzyloxyphenyl)-1-(2-hydroxy-5-methylphenyl)prop-2-en-1-one

Abstract: In the mol­ecule of the title compound, C23H20O3, an intra­molecular O—H⋯O hydrogen bond generates an S(6) ring. The central benzene ring makes dihedral angles of 80.17 (8) and 16.99 (7)°, respectively, with the benz­yloxy and hy­droxy­methyl phenyl rings. In the crystal, mol­ecules are linked via inter­molecular C—H⋯O hydrogen bonds to form dimers. The dimers are connected by C—H⋯O hydrogen bonds and C—H⋯π inter­actions to form columns down the b axis.

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Cited by 5 publications
(4 citation statements)
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“…The C2-C1-N1-N2, C1-N1-N2-C7, N1-N2-C7-C8, N2-C7-C8-Cl1, N2-C7-C8-Cl2, Cl1-C8-C7-C9 and C8-C7-C9-C14 torsion angles are À1.1 (2), 178.86 (13), 174.62 14, À176.19 (11), 2.9 (2), 5.1 (2) and 63.4 (2) , respectively. Bond lengths (Allen et al, 1987) and angles are within normal ranges and are comparable to those observed in related structures, viz: (2E)-1-(2-hydroxy-5-methylphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (Fun et al, 2011a), (2E)-3-(3-benzyloxyphenyl)-1-(2-hydroxy-5-methylphenyl)prop-2en-1-one (Fun et al, 2011b), (2E)-3-[3-(benzyloxy)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one (Fun et al, 2011c), (2E)-1-(2,5-dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one (Fun et al, 2011d) and (2E)-3-(3-nitrophenyl)-1-[4-(piperidin-1-yl)phenyl]prop-2-en-1-one (Fun et al, 2012).…”
Section: Structural Commentarysupporting
confidence: 78%
“…The C2-C1-N1-N2, C1-N1-N2-C7, N1-N2-C7-C8, N2-C7-C8-Cl1, N2-C7-C8-Cl2, Cl1-C8-C7-C9 and C8-C7-C9-C14 torsion angles are À1.1 (2), 178.86 (13), 174.62 14, À176.19 (11), 2.9 (2), 5.1 (2) and 63.4 (2) , respectively. Bond lengths (Allen et al, 1987) and angles are within normal ranges and are comparable to those observed in related structures, viz: (2E)-1-(2-hydroxy-5-methylphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (Fun et al, 2011a), (2E)-3-(3-benzyloxyphenyl)-1-(2-hydroxy-5-methylphenyl)prop-2en-1-one (Fun et al, 2011b), (2E)-3-[3-(benzyloxy)phenyl]-1-(2-hydroxyphenyl)prop-2-en-1-one (Fun et al, 2011c), (2E)-1-(2,5-dimethoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one (Fun et al, 2011d) and (2E)-3-(3-nitrophenyl)-1-[4-(piperidin-1-yl)phenyl]prop-2-en-1-one (Fun et al, 2012).…”
Section: Structural Commentarysupporting
confidence: 78%
“…At the beginning of amore comprehensive study aimed at structure-property relationships of as eries of compounds similar to the title compound, its structure was redetermined at 200 Ktoallow for comparisons of metrical parameters with other members of the series to be researched. Apartfrom the title compound, thecrystal structures of 2-(2-benzyloxyphenyl)-1H-benzimidazole [2]a nd (2E)-3-(3-benzyloxyphenyl)-1-(2-hydroxy-5-methylphenyl)-prop-2-en-1-one [3] areapparent in the literature. The molecule features a( phenylmethyloxy)benzene core that bearsa halogenated carbonyl-derived substituent in para-position.…”
Section: Discussionmentioning
confidence: 99%
“…For background to 1-((3-(benzyloxy)-2-nitrophenoxy)methyl)benzene derivatives, see: Altmann et al (2004); Ohkubo et al (1997). For related structures, see: Naveenkumar et al (2009); Fun et al (2011); Ren & Wang (2012). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).…”
Section: Related Literaturementioning
confidence: 99%
“…1), consists of two crystallographically independent molecules, A and B. Bond lengths and angles are within normal ranges (Naveenkumar et al, 2009;Fun et al, 2011;Ren & Wang, 2012). In molecule A, the central benzene ring (C8A-C13A) forms dihedral angles of 2.26 (6) and 58.68 (6)°, respectively, with the terminal benzene rings (C1A-C6A & C15A-C20A).…”
Section: -[(3-benzyloxy-2-nitrophenoxy)methyl]benzenementioning
confidence: 99%