Limits...
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.


A stereoview of part of the crystal structure of compound (XI), showing the formation of sheets parallel to (100) built from π-stacked hydrogen-bonded C(6) chains. The original atomic coordinates (Sunitha et al., 2012 ▸) have been used and, for the sake of clarity, the H atoms not involved in the motif shown have been omitted.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4555379&req=5

fig10: A stereoview of part of the crystal structure of compound (XI), showing the formation of sheets parallel to (100) built from π-stacked hydrogen-bonded C(6) chains. The original atomic coordinates (Sunitha et al., 2012 ▸) have been used and, for the sake of clarity, the H atoms not involved in the motif shown have been omitted.

Mentions: The original report on compound (XI) (Sunitha et al., 2012 ▸) provides no analysis or description of the supra­molecular assembly. Examination of the original atomic coordinates shows firstly that mol­ecules related by a c-glide plane are linked by a nearly linear C—H⋯O hydrogen bond, forming a C(6) chain running parallel to the [001] direction, and secondly that inversion-related pairs of mol­ecules are linked by a π–π stacking inter­action involving the phenyl rings of the mol­ecules at (x, y, z) and (−x + 1, −y + 1, −z), with inter­planar spacing 3.4465 (10) Å, ring-centroid separation 3.749 (3) Å and ring-centroid offset 1.475 (3) Å. The combined effect of these two types of inter­action is the formation of a sheet lying parallel to (100); see Fig. 10 ▸.


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)

A stereoview of part of the crystal structure of compound (XI), showing the formation of sheets parallel to (100) built from π-stacked hydrogen-bonded C(6) chains. The original atomic coordinates (Sunitha et al., 2012 ▸) have been used and, for the sake of clarity, the H atoms not involved in the motif shown have been omitted.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig10: A stereoview of part of the crystal structure of compound (XI), showing the formation of sheets parallel to (100) built from π-stacked hydrogen-bonded C(6) chains. The original atomic coordinates (Sunitha et al., 2012 ▸) have been used and, for the sake of clarity, the H atoms not involved in the motif shown have been omitted.
Mentions: The original report on compound (XI) (Sunitha et al., 2012 ▸) provides no analysis or description of the supra­molecular assembly. Examination of the original atomic coordinates shows firstly that mol­ecules related by a c-glide plane are linked by a nearly linear C—H⋯O hydrogen bond, forming a C(6) chain running parallel to the [001] direction, and secondly that inversion-related pairs of mol­ecules are linked by a π–π stacking inter­action involving the phenyl rings of the mol­ecules at (x, y, z) and (−x + 1, −y + 1, −z), with inter­planar spacing 3.4465 (10) Å, ring-centroid separation 3.749 (3) Å and ring-centroid offset 1.475 (3) Å. The combined effect of these two types of inter­action is the formation of a sheet lying parallel to (100); see Fig. 10 ▸.

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.