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Crystal structures of ethyl {2-[4-(4-iso ­ propyl ­ phen ­ yl)thia ­ zol-2-yl]phen ­ yl}carbamate and ethyl {2-[4-(3-nitro ­ phen ­ yl)thia ­ zol-2-yl]phen ­ yl}carbamate

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ABSTRACT

The title compounds, C21H22N2O2S (I) and C18H15N3O4S (II), are structural analogs of the alkaloid Thio­sporine B. Both mol­ecules adopt a near-planar V-shaped conformation, which is consolidated by intra­molecular N—H⋯N and C—H⋯O hydrogen bonds. The crystal structure of (I) consists of mlecular stacks along the a axis, in which the mol­ecules are linked to each other by π(S)⋯π(C) inter­actions. In the crystal of (II), mol­ecules are linked into chains by C—H⋯O hydrogen bonds and the chains are cross-linked into (100) sheets by π–π stacking inter­actions.

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The mol­ecular structure of (II). Displacement ellipsoids are shown at the 50% probability level. Dashed lines indicate the intra­molecular hydrogen bonds. H atoms are presented as small spheres of arbitrary radius.
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fig2: The mol­ecular structure of (II). Displacement ellipsoids are shown at the 50% probability level. Dashed lines indicate the intra­molecular hydrogen bonds. H atoms are presented as small spheres of arbitrary radius.

Mentions: Compounds (I), C21H22N2O2S, and (II), C18H15N3O4S, have very similar mol­ecular geometries (Figs. 1 ▸ and 2 ▸), allowing for the different substituents on the benzene rings. Both mol­ecules adopt a near-planar V-shaped conformation, which is consolidated by intra­molecular N7—H7⋯N3 and C8—H8⋯O1 hydrogen bonds (Tables 1 ▸ and 2 ▸, Figs. 1 ▸ and 2 ▸) as well as an inter­molecular π–π inter­actions (see Section 3 below). There exists a small twist of 10.27 (15)° between the central thia­zole and 4-benzene rings in (I) only. Surprisingly, the ethyl (phen­yl)carbamate substituents (with the exception of some hydrogen atoms of the ethyl fragment) are perfectly coplanar with the thia­zole ring in both mol­ecules.


Crystal structures of ethyl {2-[4-(4-iso ­ propyl ­ phen ­ yl)thia ­ zol-2-yl]phen ­ yl}carbamate and ethyl {2-[4-(3-nitro ­ phen ­ yl)thia ­ zol-2-yl]phen ­ yl}carbamate
The mol­ecular structure of (II). Displacement ellipsoids are shown at the 50% probability level. Dashed lines indicate the intra­molecular hydrogen bonds. H atoms are presented as small spheres of arbitrary radius.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5120716&req=5

fig2: The mol­ecular structure of (II). Displacement ellipsoids are shown at the 50% probability level. Dashed lines indicate the intra­molecular hydrogen bonds. H atoms are presented as small spheres of arbitrary radius.
Mentions: Compounds (I), C21H22N2O2S, and (II), C18H15N3O4S, have very similar mol­ecular geometries (Figs. 1 ▸ and 2 ▸), allowing for the different substituents on the benzene rings. Both mol­ecules adopt a near-planar V-shaped conformation, which is consolidated by intra­molecular N7—H7⋯N3 and C8—H8⋯O1 hydrogen bonds (Tables 1 ▸ and 2 ▸, Figs. 1 ▸ and 2 ▸) as well as an inter­molecular π–π inter­actions (see Section 3 below). There exists a small twist of 10.27 (15)° between the central thia­zole and 4-benzene rings in (I) only. Surprisingly, the ethyl (phen­yl)carbamate substituents (with the exception of some hydrogen atoms of the ethyl fragment) are perfectly coplanar with the thia­zole ring in both mol­ecules.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The title compounds, C21H22N2O2S (I) and C18H15N3O4S (II), are structural analogs of the alkaloid Thio­sporine B. Both mol­ecules adopt a near-planar V-shaped conformation, which is consolidated by intra­molecular N—H⋯N and C—H⋯O hydrogen bonds. The crystal structure of (I) consists of mlecular stacks along the a axis, in which the mol­ecules are linked to each other by π(S)⋯π(C) inter­actions. In the crystal of (II), mol­ecules are linked into chains by C—H⋯O hydrogen bonds and the chains are cross-linked into (100) sheets by π–π stacking inter­actions.

No MeSH data available.