Limits...
Crystal structures of two C,N-disubstituted acetamides: 2-(4-chloro ­ phen ­ yl)- N -(2-iodo ­ phen ­ yl)acetamide and 2-(4-chloro ­ phen ­ yl)- N -(pyrazin-2-yl)acetamide

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the crystal of 2-(4-chloro­phen­yl)-N-(2-iodo­phen­yl)acetamide, C14H11ClINO, mol­ecules are linked by a combination of N—H⋯O and C—H⋯O hydrogen bonds to form a C(4)C(4)[R21(7)] chain of rings and chains of this type are linked by a combination of C—Cl⋯π(arene) and C—I⋯π(arene) inter­actions to form deeply puckered twofold inter­woven sheets. In the crystal of 2-(4-chloro­phen­yl)-N-(pyrazin-2-yl)acetamide, C12H10ClN3O, mol­ecules are linked into complex sheets by N—H⋯N, C—H⋯N and C—H⋯O hydrogen bonds, and by C—H⋯π(arene) inter­actions.

No MeSH data available.


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

License
getmorefigures.php?uid=PMC5120705&req=5

fig2: The mol­ecular structure of compound (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Mentions: The mol­ecular conformations of compounds (I) and (II), illustrated in Figs. 1 ▸ and 2 ▸, respectively, can be defined in terms of the torsional angles N1—C1—C2—C21, 141.8 (3) and 129.22 (18)° respectively, and by the dihedral angles between the central spacer unit, atoms N1,C1,O1,C2, and the two independent rings. The dihedral angles to the chlorinated ring (C21–C26) are 80.02 (11) and 61.74 (6)° in (I) and (II); those to the iodinated ring in (I) and the pyrazinyl ring in (II) are 67.48 (11) and 5.86 (11)°, respectively. This difference is probably associated with the participation in the inter­molecular hydrogen bond of both N atoms of the pyrazinyl ring in (II), as discussed below. The mol­ecules of (I) and (II) do not therefore exhibit any inter­nal symmetry, so that they are conformationally chiral: the centrosymmetric space groups confirm that each compound has crystallized as a conformational racemate.


Crystal structures of two C,N-disubstituted acetamides: 2-(4-chloro ­ phen ­ yl)- N -(2-iodo ­ phen ­ yl)acetamide and 2-(4-chloro ­ phen ­ yl)- N -(pyrazin-2-yl)acetamide
The mol­ecular structure of compound (II), 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=PMC5120705&req=5

fig2: The mol­ecular structure of compound (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
Mentions: The mol­ecular conformations of compounds (I) and (II), illustrated in Figs. 1 ▸ and 2 ▸, respectively, can be defined in terms of the torsional angles N1—C1—C2—C21, 141.8 (3) and 129.22 (18)° respectively, and by the dihedral angles between the central spacer unit, atoms N1,C1,O1,C2, and the two independent rings. The dihedral angles to the chlorinated ring (C21–C26) are 80.02 (11) and 61.74 (6)° in (I) and (II); those to the iodinated ring in (I) and the pyrazinyl ring in (II) are 67.48 (11) and 5.86 (11)°, respectively. This difference is probably associated with the participation in the inter­molecular hydrogen bond of both N atoms of the pyrazinyl ring in (II), as discussed below. The mol­ecules of (I) and (II) do not therefore exhibit any inter­nal symmetry, so that they are conformationally chiral: the centrosymmetric space groups confirm that each compound has crystallized as a conformational racemate.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

In the crystal of 2-(4-chloro­phen­yl)-N-(2-iodo­phen­yl)acetamide, C14H11ClINO, mol­ecules are linked by a combination of N—H⋯O and C—H⋯O hydrogen bonds to form a C(4)C(4)[R21(7)] chain of rings and chains of this type are linked by a combination of C—Cl⋯π(arene) and C—I⋯π(arene) inter­actions to form deeply puckered twofold inter­woven sheets. In the crystal of 2-(4-chloro­phen­yl)-N-(pyrazin-2-yl)acetamide, C12H10ClN3O, mol­ecules are linked into complex sheets by N—H⋯N, C—H⋯N and C—H⋯O hydrogen bonds, and by C—H⋯π(arene) inter­actions.

No MeSH data available.