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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

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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.


A projection down [001] of one of the (100) sheets in the crystal structure of compound (I) showing the deep puckering of the sheet enabling inter­weaving. The C—X⋯π(arene) inter­actions (X = Cl or I) are shown as thin tapered lines, and for the sake of clarity, the H atoms have all been omitted.
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fig5: A projection down [001] of one of the (100) sheets in the crystal structure of compound (I) showing the deep puckering of the sheet enabling inter­weaving. The C—X⋯π(arene) inter­actions (X = Cl or I) are shown as thin tapered lines, and for the sake of clarity, the H atoms have all been omitted.

Mentions: Because the repeat unit of this sheet in the [010] direction spans two unit cells, there are in fact two such sheets present, related to one another by a unit translation along [010]: the deep puckering of the sheets (Fig. 5 ▸) means that the two independent sheets are inter­woven. The structure of (I) also contains a short I⋯O contact with dimension I12⋯O1i 3.058 (2) Å and C12—I12⋯O1i 170.88 (8)° [symmetry code: (i) x,  − y,  + z] which complements the C—Cl⋯Cg contact. The I⋯O distance here is significantly shorter than the sum of the van der Waals radii, 3.56 Å (Rowland & Taylor, 1996 ▸), or 3.30 Å if account is taken of the polar flattening model (Nyburg & Faerman, 1985 ▸).


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
A projection down [001] of one of the (100) sheets in the crystal structure of compound (I) showing the deep puckering of the sheet enabling inter­weaving. The C—X⋯π(arene) inter­actions (X = Cl or I) are shown as thin tapered lines, and for the sake of clarity, the H atoms have all been omitted.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5120705&req=5

fig5: A projection down [001] of one of the (100) sheets in the crystal structure of compound (I) showing the deep puckering of the sheet enabling inter­weaving. The C—X⋯π(arene) inter­actions (X = Cl or I) are shown as thin tapered lines, and for the sake of clarity, the H atoms have all been omitted.
Mentions: Because the repeat unit of this sheet in the [010] direction spans two unit cells, there are in fact two such sheets present, related to one another by a unit translation along [010]: the deep puckering of the sheets (Fig. 5 ▸) means that the two independent sheets are inter­woven. The structure of (I) also contains a short I⋯O contact with dimension I12⋯O1i 3.058 (2) Å and C12—I12⋯O1i 170.88 (8)° [symmetry code: (i) x,  − y,  + z] which complements the C—Cl⋯Cg contact. The I⋯O distance here is significantly shorter than the sum of the van der Waals radii, 3.56 Å (Rowland & Taylor, 1996 ▸), or 3.30 Å if account is taken of the polar flattening model (Nyburg & Faerman, 1985 ▸).

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.