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The crystal structures of six (2E)-3-aryl-1-(5-halogeno-thio-phen-2-yl)prop-2-en-1-ones.

Naik VS, Yathirajan HS, Jasinski JP, Smolenski VA, Glidewell C - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The structures of six chalcones containing 5-halogeno-thio-phen-2-yl substituents are reported: (2E)-1-(5-chloro-thio-phen-2-yl)-3-(4-ethyl-phen-yl)prop-2-en-1-one, C15H13ClOS, (I), and (2E)-1-(5-bromo-thio-phen-2-yl)-3-(4-ethyl-phen-yl)prop-2-en-1-one, C15H13BrOS, (II), are isostructural in space group P-1, while (2E)-1-(5-chloro-thio-phen-2-yl)-3-(4-eth-oxy-phen-yl)prop-2-en-1-one, C15H13ClO2S, (III), and (2E)-1-(5-bromo-thio-phen-2-yl)-3-(4-eth-oxy-phen-yl)prop-2-en-1-one C15H13BrO2S, (IV), are isostructural in space group P21/c.In each of compounds (I)-(VI), the mol-ecular skeletons are close to planarity, and there are short halogen⋯halogen contacts in the structures of compounds (II) and (V) and a short Br⋯O contact in the structure of compound (VI).Comparisons are made with the structures of some similar compounds.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Physics, Government First Grade College, Kumta 581 343, India, Research and Development Centre, Bharathiar University, Coimbatore 641 046, India.

ABSTRACT
The structures of six chalcones containing 5-halogeno-thio-phen-2-yl substituents are reported: (2E)-1-(5-chloro-thio-phen-2-yl)-3-(4-ethyl-phen-yl)prop-2-en-1-one, C15H13ClOS, (I), and (2E)-1-(5-bromo-thio-phen-2-yl)-3-(4-ethyl-phen-yl)prop-2-en-1-one, C15H13BrOS, (II), are isostructural in space group P-1, while (2E)-1-(5-chloro-thio-phen-2-yl)-3-(4-eth-oxy-phen-yl)prop-2-en-1-one, C15H13ClO2S, (III), and (2E)-1-(5-bromo-thio-phen-2-yl)-3-(4-eth-oxy-phen-yl)prop-2-en-1-one C15H13BrO2S, (IV), are isostructural in space group P21/c. There are no hydrogen bonds of any kind in the structures of compounds (I) and (II), but in the structures of compounds (III) and (IV), the mol-ecules are linked into C(7) chains by means of C-H⋯O hydrogen bonds. In the structure of (2E)-3-(4-bromo-phen-yl)-1-(5-chloro-thio-phen-2-yl)prop-2-en-1-one, C13H8BrClOS, (V), there are again no hydrogen bonds nor π-π stacking inter-actions but in that of (2E)-1-(5-bromo-thio-phen-2-yl)-3-(3-meth-oxy-phen-yl)prop-2-en-1-one, C14H11BrO2S, (VI), the mol-ecules are linked into C(5) chains by C-H⋯O hydrogen bonds. In each of compounds (I)-(VI), the mol-ecular skeletons are close to planarity, and there are short halogen⋯halogen contacts in the structures of compounds (II) and (V) and a short Br⋯O contact in the structure of compound (VI). Comparisons are made with the structures of some similar compounds.

No MeSH data available.


The mol­ecular structure of compound (VI), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
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fig6: The mol­ecular structure of compound (VI), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Mentions: Chalcones are important constituents of many natural products, and they are abundant in edible plants where they are considered to be precursors of flavonoids and isoflavonoids. They display a wide range of pharmacological properties including anti­bacterial (Tang et al., 2008 ▸; Kumar et al., 2013a ▸), anti­cancer (Shin et al., 2013 ▸), anti­fungal (Domínguez et al., 2001 ▸; Kumar et al., 2013a ▸,b ▸), anti­malarial (Li et al., 1995 ▸) and anti­tubercular (Lin et al., 2002 ▸) activity. In addition, chalcone derivatives are also important materials in photonic applications because of their excellent blue-light transmittance and good crystallization ability (Goto et al., 1991 ▸; Uchida et al.,1998 ▸; Indira et al., 2002 ▸; Sarojini et al., 2006 ▸). In a continuation of our work on chalcones containing a thio­phen moiety (Naik et al., 2015 ▸), six new chalcones of this type, compounds (I)–(VI) (Figs. 1 ▸–6 ▸ ▸ ▸ ▸ ▸) have now been synthesized and we report herein on their mol­ecular structures and supra­molecular assembly. Compounds (I)–(VI) were all prepared using condensation reactions, under basic conditions, between 2-acetyl-5-halogeno­thio­phens and substituted benzaldehydes.


The crystal structures of six (2E)-3-aryl-1-(5-halogeno-thio-phen-2-yl)prop-2-en-1-ones.

Naik VS, Yathirajan HS, Jasinski JP, Smolenski VA, Glidewell C - Acta Crystallogr E Crystallogr Commun (2015)

The mol­ecular structure of compound (VI), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4555379&req=5

fig6: The mol­ecular structure of compound (VI), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
Mentions: Chalcones are important constituents of many natural products, and they are abundant in edible plants where they are considered to be precursors of flavonoids and isoflavonoids. They display a wide range of pharmacological properties including anti­bacterial (Tang et al., 2008 ▸; Kumar et al., 2013a ▸), anti­cancer (Shin et al., 2013 ▸), anti­fungal (Domínguez et al., 2001 ▸; Kumar et al., 2013a ▸,b ▸), anti­malarial (Li et al., 1995 ▸) and anti­tubercular (Lin et al., 2002 ▸) activity. In addition, chalcone derivatives are also important materials in photonic applications because of their excellent blue-light transmittance and good crystallization ability (Goto et al., 1991 ▸; Uchida et al.,1998 ▸; Indira et al., 2002 ▸; Sarojini et al., 2006 ▸). In a continuation of our work on chalcones containing a thio­phen moiety (Naik et al., 2015 ▸), six new chalcones of this type, compounds (I)–(VI) (Figs. 1 ▸–6 ▸ ▸ ▸ ▸ ▸) have now been synthesized and we report herein on their mol­ecular structures and supra­molecular assembly. Compounds (I)–(VI) were all prepared using condensation reactions, under basic conditions, between 2-acetyl-5-halogeno­thio­phens and substituted benzaldehydes.

Bottom Line: The structures of six chalcones containing 5-halogeno-thio-phen-2-yl substituents are reported: (2E)-1-(5-chloro-thio-phen-2-yl)-3-(4-ethyl-phen-yl)prop-2-en-1-one, C15H13ClOS, (I), and (2E)-1-(5-bromo-thio-phen-2-yl)-3-(4-ethyl-phen-yl)prop-2-en-1-one, C15H13BrOS, (II), are isostructural in space group P-1, while (2E)-1-(5-chloro-thio-phen-2-yl)-3-(4-eth-oxy-phen-yl)prop-2-en-1-one, C15H13ClO2S, (III), and (2E)-1-(5-bromo-thio-phen-2-yl)-3-(4-eth-oxy-phen-yl)prop-2-en-1-one C15H13BrO2S, (IV), are isostructural in space group P21/c.In each of compounds (I)-(VI), the mol-ecular skeletons are close to planarity, and there are short halogen⋯halogen contacts in the structures of compounds (II) and (V) and a short Br⋯O contact in the structure of compound (VI).Comparisons are made with the structures of some similar compounds.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Physics, Government First Grade College, Kumta 581 343, India, Research and Development Centre, Bharathiar University, Coimbatore 641 046, India.

ABSTRACT
The structures of six chalcones containing 5-halogeno-thio-phen-2-yl substituents are reported: (2E)-1-(5-chloro-thio-phen-2-yl)-3-(4-ethyl-phen-yl)prop-2-en-1-one, C15H13ClOS, (I), and (2E)-1-(5-bromo-thio-phen-2-yl)-3-(4-ethyl-phen-yl)prop-2-en-1-one, C15H13BrOS, (II), are isostructural in space group P-1, while (2E)-1-(5-chloro-thio-phen-2-yl)-3-(4-eth-oxy-phen-yl)prop-2-en-1-one, C15H13ClO2S, (III), and (2E)-1-(5-bromo-thio-phen-2-yl)-3-(4-eth-oxy-phen-yl)prop-2-en-1-one C15H13BrO2S, (IV), are isostructural in space group P21/c. There are no hydrogen bonds of any kind in the structures of compounds (I) and (II), but in the structures of compounds (III) and (IV), the mol-ecules are linked into C(7) chains by means of C-H⋯O hydrogen bonds. In the structure of (2E)-3-(4-bromo-phen-yl)-1-(5-chloro-thio-phen-2-yl)prop-2-en-1-one, C13H8BrClOS, (V), there are again no hydrogen bonds nor π-π stacking inter-actions but in that of (2E)-1-(5-bromo-thio-phen-2-yl)-3-(3-meth-oxy-phen-yl)prop-2-en-1-one, C14H11BrO2S, (VI), the mol-ecules are linked into C(5) chains by C-H⋯O hydrogen bonds. In each of compounds (I)-(VI), the mol-ecular skeletons are close to planarity, and there are short halogen⋯halogen contacts in the structures of compounds (II) and (V) and a short Br⋯O contact in the structure of compound (VI). Comparisons are made with the structures of some similar compounds.

No MeSH data available.