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Comparison of crystal structures of 4-(benzo[b]thio-phen-2-yl)-5-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole and 4-(benzo[b]thio-phen-2-yl)-2-methyl-5-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole.

Penthala NR, Madadi NR, Bommagani S, Parkin S, Crooks PA - Acta Crystallogr Sect E Struct Rep Online (2014)

Bottom Line: In (I) and (II), the triazole rings make dihedral angles of 32.68 (5) and 10.43 (8)°, respectively, with the mean planes of the benzo-thio-phene ring systems.The trimeth-oxy phenyl rings make dihedral angles with the benzo-thio-phene rings of 38.48 (4) in (I) and 60.43 (5)° in (II).After the N-methyl-ation of structure (I), no hydrogen-bonding inter-actions were observed for structure (II).

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.

ABSTRACT
The title compound, C19H17N3O3S (I), was prepared by a [3 + 2]cyclo-addition azide condensation reaction using sodium azide and l-proline as a Lewis base catalyst. N-Methyl-ation of compound (I) using CH3I gave compound (II), C20H19N3O3S. The benzo-thio-phene ring systems in (I) and (II) are almost planar, with r.m.s deviations from the mean plane = 0.0205 (14) in (I) and 0.016 (2) Å in (II). In (I) and (II), the triazole rings make dihedral angles of 32.68 (5) and 10.43 (8)°, respectively, with the mean planes of the benzo-thio-phene ring systems. The trimeth-oxy phenyl rings make dihedral angles with the benzo-thio-phene rings of 38.48 (4) in (I) and 60.43 (5)° in (II). In the crystal of (I), the mol-ecules are linked into chains by N-H⋯O hydrogen bonds with R (2) 1(5) ring motifs. After the N-methyl-ation of structure (I), no hydrogen-bonding inter-actions were observed for structure (II). The crystal structure of (II) has a minor component of disorder that corresponds to a 180° flip of the benzo-thio-phene ring system [occupancy ratio 0.9363 (14):0.0637 (14)].

No MeSH data available.


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The mol­ecular structure of (II), with displacement ellipsoids drawn at the 50% probability level.
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fig2: The mol­ecular structure of (II), with displacement ellipsoids drawn at the 50% probability level.

Mentions: In order to obtain detailed information on the structural conformations of (I) and (II) for analysis of structure–activity relationships (SAR), including the position of the hydrogen atom in the triazole ring system of (I) and the position of methyl­ation on the triazole ring system in (II), we determined the X-ray crystal structures of (I) and (II); see Figs. 1 ▶ and 2 ▶, respectively.


Comparison of crystal structures of 4-(benzo[b]thio-phen-2-yl)-5-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole and 4-(benzo[b]thio-phen-2-yl)-2-methyl-5-(3,4,5-tri-meth-oxy-phen-yl)-2H-1,2,3-triazole.

Penthala NR, Madadi NR, Bommagani S, Parkin S, Crooks PA - Acta Crystallogr Sect E Struct Rep Online (2014)

The mol­ecular structure of (II), with displacement ellipsoids drawn at the 50% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4257340&req=5

fig2: The mol­ecular structure of (II), with displacement ellipsoids drawn at the 50% probability level.
Mentions: In order to obtain detailed information on the structural conformations of (I) and (II) for analysis of structure–activity relationships (SAR), including the position of the hydrogen atom in the triazole ring system of (I) and the position of methyl­ation on the triazole ring system in (II), we determined the X-ray crystal structures of (I) and (II); see Figs. 1 ▶ and 2 ▶, respectively.

Bottom Line: In (I) and (II), the triazole rings make dihedral angles of 32.68 (5) and 10.43 (8)°, respectively, with the mean planes of the benzo-thio-phene ring systems.The trimeth-oxy phenyl rings make dihedral angles with the benzo-thio-phene rings of 38.48 (4) in (I) and 60.43 (5)° in (II).After the N-methyl-ation of structure (I), no hydrogen-bonding inter-actions were observed for structure (II).

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.

ABSTRACT
The title compound, C19H17N3O3S (I), was prepared by a [3 + 2]cyclo-addition azide condensation reaction using sodium azide and l-proline as a Lewis base catalyst. N-Methyl-ation of compound (I) using CH3I gave compound (II), C20H19N3O3S. The benzo-thio-phene ring systems in (I) and (II) are almost planar, with r.m.s deviations from the mean plane = 0.0205 (14) in (I) and 0.016 (2) Å in (II). In (I) and (II), the triazole rings make dihedral angles of 32.68 (5) and 10.43 (8)°, respectively, with the mean planes of the benzo-thio-phene ring systems. The trimeth-oxy phenyl rings make dihedral angles with the benzo-thio-phene rings of 38.48 (4) in (I) and 60.43 (5)° in (II). In the crystal of (I), the mol-ecules are linked into chains by N-H⋯O hydrogen bonds with R (2) 1(5) ring motifs. After the N-methyl-ation of structure (I), no hydrogen-bonding inter-actions were observed for structure (II). The crystal structure of (II) has a minor component of disorder that corresponds to a 180° flip of the benzo-thio-phene ring system [occupancy ratio 0.9363 (14):0.0637 (14)].

No MeSH data available.


Related in: MedlinePlus