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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.


Related in: MedlinePlus

Part of the crystal structure of compound (I) showing the formation of a hydrogen-bonded chain of rings running parallel to the [001] direction. Hydrogen bonds are shown as dashed lines and, for the sake of clarity, the H atoms bonded to the C atoms which are not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x,  − y,  + z) and (x,  − y, − + z), respectively.
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fig3: Part of the crystal structure of compound (I) showing the formation of a hydrogen-bonded chain of rings running parallel to the [001] direction. Hydrogen bonds are shown as dashed lines and, for the sake of clarity, the H atoms bonded to the C atoms which are not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x,  − y,  + z) and (x,  − y, − + z), respectively.

Mentions: The hydrogen-bonded assembly in compound (I) is very simple: a combination of N—H⋯O and C—H⋯O hydrogen bonds (Table 1 ▸) links the mol­ecules into a C(4)C(4)[(6)] chain of rings. This chain contains mol­ecules which are related by a c-glide plane, producing a chain running parallel to the [001] direction (Fig. 3 ▸). There is also a C—H⋯π(arene) contact in compound (I) (Table 1 ▸), lying within the [001] chain, but the dimensions make it unlikely that this has any structural significance. Two chains of this type, which are related to one another by inversion, pass through each unit cell, and a combination of C—I⋯π(arene) and C—Cl⋯π(arene) inter­actions links the chains into a sheet in the form of a (4,4) net lying parallel to (100) (Fig. 4 ▸). The dimensions of these inter­actions are: for C12—I12⋯Cg1i [symmetry code: (i) x,  − y,  + z, where Cg1 represents the centroid of the C11–C16] ring, I⋯Cg 3.7977 (14), C⋯Cg 5.082 (3) Å and C—I⋯Cg 116.34 (8)°; for C24—Cl24⋯Cg2ii [symmetry code: (ii) x, − − y, − + z, where Cg2 represents the centroid of the C21–C26 ring], Cl⋯Cg 3.4557 (8), C⋯Cg 4.504 (3) Å and C—Cl⋯Cg 116.19 (11)°. The metrics of the C—Cl⋯Cg inter­action are well within the normal range, as deduced using database analysis (Imai et al., 2008 ▸).


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
Part of the crystal structure of compound (I) showing the formation of a hydrogen-bonded chain of rings running parallel to the [001] direction. Hydrogen bonds are shown as dashed lines and, for the sake of clarity, the H atoms bonded to the C atoms which are not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x,  − y,  + z) and (x,  − y, − + z), respectively.
© Copyright Policy - open-access
Related In: Results  -  Collection

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

fig3: Part of the crystal structure of compound (I) showing the formation of a hydrogen-bonded chain of rings running parallel to the [001] direction. Hydrogen bonds are shown as dashed lines and, for the sake of clarity, the H atoms bonded to the C atoms which are not involved in the motif shown have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x,  − y,  + z) and (x,  − y, − + z), respectively.
Mentions: The hydrogen-bonded assembly in compound (I) is very simple: a combination of N—H⋯O and C—H⋯O hydrogen bonds (Table 1 ▸) links the mol­ecules into a C(4)C(4)[(6)] chain of rings. This chain contains mol­ecules which are related by a c-glide plane, producing a chain running parallel to the [001] direction (Fig. 3 ▸). There is also a C—H⋯π(arene) contact in compound (I) (Table 1 ▸), lying within the [001] chain, but the dimensions make it unlikely that this has any structural significance. Two chains of this type, which are related to one another by inversion, pass through each unit cell, and a combination of C—I⋯π(arene) and C—Cl⋯π(arene) inter­actions links the chains into a sheet in the form of a (4,4) net lying parallel to (100) (Fig. 4 ▸). The dimensions of these inter­actions are: for C12—I12⋯Cg1i [symmetry code: (i) x,  − y,  + z, where Cg1 represents the centroid of the C11–C16] ring, I⋯Cg 3.7977 (14), C⋯Cg 5.082 (3) Å and C—I⋯Cg 116.34 (8)°; for C24—Cl24⋯Cg2ii [symmetry code: (ii) x, − − y, − + z, where Cg2 represents the centroid of the C21–C26 ring], Cl⋯Cg 3.4557 (8), C⋯Cg 4.504 (3) Å and C—Cl⋯Cg 116.19 (11)°. The metrics of the C—Cl⋯Cg inter­action are well within the normal range, as deduced using database analysis (Imai et al., 2008 ▸).

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.


Related in: MedlinePlus