Crystal structures of two C,N-disubstituted acetamides: 2-(4-chlorophenyl)-N-(2-iodophenyl)acetamide and 2-(4-chlorophenyl)-N-(pyrazin-2-yl)acetamide

Badiadka Narayana; Hemmige S. Yathirajan; Ravindranath Rathore; Christopher Glidewell

doi:10.1107/S2056989016012512

Crystal structures of two C,N-disubstituted acetamides: 2-(4-chlorophenyl)-N-(2-iodophenyl)acetamide and 2-(4-chlorophenyl)-N-(pyrazin-2-yl)acetamide

Badiadka Narayana, Hemmige S. Yathirajan, Ravindranath Rathore, Christopher Glidewell

School of Chemistry

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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.

Original language	English
Pages (from-to)	1270-1275
Number of pages	6
Journal	Acta Crystallographica Section E: Crystallographic Communications
Volume	72
Issue number	9
DOIs	https://doi.org/10.1107/S2056989016012512
Publication status	Published - 1 Sept 2016

Keywords

Crystal structure
C,N-disubstituted acetamides
Molecular structure
Molecular conformation
Hydrogen bonding
C-halogen...[pi] bonding] bonding

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Glidewell_2016_ACSE_C,N-disubstitutedAcetamides_CC
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Crystal structures of two C,N-disubstituted acetamides: 2-(4-chlorophenyl)-N-(2-iodophenyl)acetamide and 2-(4-chlorophenyl)-N-(pyrazin-2-yl)acetamide (dataset)
Narayana, B. (Creator), Yathirajan, H. S. (Creator), Rathore, R. (Creator) & Glidewell, C. (Creator), Cambridge Crystallographic Data Centre, 2016
https://dx.doi.org/10.5517/ccdc.csd.cc1m83xx and one more link, https://dx.doi.org/10.5517/ccdc.csd.cc1m83yy (show fewer)
Dataset

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@article{b0db7e0abb3e466f9011d0ae4935fa22,

title = "Crystal structures of two C,N-disubstituted acetamides: 2-(4-chlorophenyl)-N-(2-iodophenyl)acetamide and 2-(4-chlorophenyl)-N-(pyrazin-2-yl)acetamide",

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.",

keywords = "Crystal structure, C,N-disubstituted acetamides, Molecular structure, Molecular conformation, Hydrogen bonding, C-halogen...[pi] bonding] bonding",

author = "Badiadka Narayana and Yathirajan, {Hemmige S.} and Ravindranath Rathore and Christopher Glidewell",

note = "BN thanks the UGC (India) for financial assistance through a BSR one-time grant for the purchase of chemicals.",

year = "2016",

month = sep,

day = "1",

doi = "10.1107/S2056989016012512",

language = "English",

volume = "72",

pages = "1270--1275",

journal = "Acta Crystallographica Section E: Crystallographic Communications ",

issn = "2056-9890",

publisher = "International Union of Crystallography",

number = "9",

}

Crystal structures of two C,N-disubstituted acetamides: 2-(4-chlorophenyl)-N-(2-iodophenyl)acetamide and 2-(4-chlorophenyl)-N-(pyrazin-2-yl)acetamide. / Narayana, Badiadka; Yathirajan, Hemmige S.; Rathore, Ravindranath et al.
In: Acta Crystallographica Section E: Crystallographic Communications , Vol. 72, No. 9, 01.09.2016, p. 1270-1275.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Crystal structures of two C,N-disubstituted acetamides: 2-(4-chlorophenyl)-N-(2-iodophenyl)acetamide and 2-(4-chlorophenyl)-N-(pyrazin-2-yl)acetamide

AU - Narayana, Badiadka

AU - Yathirajan, Hemmige S.

AU - Rathore, Ravindranath

AU - Glidewell, Christopher

N1 - BN thanks the UGC (India) for financial assistance through a BSR one-time grant for the purchase of chemicals.

PY - 2016/9/1

Y1 - 2016/9/1

N2 - 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.

AB - 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.

KW - Crystal structure

KW - C,N-disubstituted acetamides

KW - Molecular structure

KW - Molecular conformation

KW - Hydrogen bonding

KW - C-halogen...[pi] bonding] bonding

U2 - 10.1107/S2056989016012512

DO - 10.1107/S2056989016012512

M3 - Article

SN - 2056-9890

VL - 72

SP - 1270

EP - 1275

JO - Acta Crystallographica Section E: Crystallographic Communications

JF - Acta Crystallographica Section E: Crystallographic Communications

IS - 9

ER -

Crystal structures of two C,N-disubstituted acetamides: 2-(4-chlorophenyl)-N-(2-iodophenyl)acetamide and 2-(4-chlorophenyl)-N-(pyrazin-2-yl)acetamide

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Crystal structures of two C,N-disubstituted acetamides: 2-(4-chlorophenyl)-N-(2-iodophenyl)acetamide and 2-(4-chlorophenyl)-N-(pyrazin-2-yl)acetamide (dataset)

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