Isonicotinamide-2-naphthoic acid (1/1)

Lee G. Madeley; Demetrius C. Levendis; Andreas Lemmerer

doi:10.1107/S1600536811050057

Isonicotinamide-2-naphthoic acid (1/1)

Lee G. Madeley
, Demetrius C. Levendis
, Andreas Lemmerer

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

3 Scopus citations

Abstract

In the title 1:1 adduct, C₆H₆N₂O· C₁₁H₈O₂, the amide group is slightly twisted out of the plane of the aromatic ring, with a C-C-C-N torsion angle of 25.11 (19)°, whereas the carboxylic acid group is approximately coplanar with the bicylic ring system, with a C-C-C-O torsion angle of 10.9 (2)°. The amide groups from two isonicotinamide molecules form a dimer via N-H⋯O hydrogen bonds. In addition, the 2-naphthanoic acid molecule is hydrogen bonded to the pyridine unit of an isonicotinamide molecule via an O-H⋯N hydrogen bond. This gives rise to a centrosymmetric four-molecule chain, which is cross-linked by further N-H⋯O hydrogen bonds from the amide group.

Original language	English
Pages (from-to)	o3440
Journal	Acta Crystallographica Section E: Structure Reports Online
Volume	67
Issue number	12
DOIs	https://doi.org/10.1107/S1600536811050057
State	Published - 1 Dec 2011
Externally published	Yes

Keywords

R factor = 0.041
T = 173 K
data-to-parameter ratio = 12.3
mean σ(C-C) = 0.002 Å
single-crystal X-ray study
wR factor = 0.119

ASJC Scopus subject areas

General Chemistry
General Materials Science
Condensed Matter Physics

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10.1107/S1600536811050057

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@article{5af28c1197bc4207a92b6824260dfa0f,

title = "Isonicotinamide-2-naphthoic acid (1/1)",

abstract = "In the title 1:1 adduct, C6H6N2O· C11H8O2, the amide group is slightly twisted out of the plane of the aromatic ring, with a C-C-C-N torsion angle of 25.11 (19)°, whereas the carboxylic acid group is approximately coplanar with the bicylic ring system, with a C-C-C-O torsion angle of 10.9 (2)°. The amide groups from two isonicotinamide molecules form a dimer via N-H⋯O hydrogen bonds. In addition, the 2-naphthanoic acid molecule is hydrogen bonded to the pyridine unit of an isonicotinamide molecule via an O-H⋯N hydrogen bond. This gives rise to a centrosymmetric four-molecule chain, which is cross-linked by further N-H⋯O hydrogen bonds from the amide group.",

keywords = "R factor = 0.041, T = 173 K, data-to-parameter ratio = 12.3, mean σ(C-C) = 0.002 {\AA}, single-crystal X-ray study, wR factor = 0.119",

author = "Madeley, \{Lee G.\} and Levendis, \{Demetrius C.\} and Andreas Lemmerer",

year = "2011",

month = dec,

day = "1",

doi = "10.1107/S1600536811050057",

language = "English",

volume = "67",

pages = "o3440",

journal = "Acta Crystallographica Section E: Structure Reports Online",

issn = "1600-5368",

publisher = "International Union of Crystallography",

number = "12",

}

TY - JOUR

T1 - Isonicotinamide-2-naphthoic acid (1/1)

AU - Madeley, Lee G.

AU - Levendis, Demetrius C.

AU - Lemmerer, Andreas

PY - 2011/12/1

Y1 - 2011/12/1

N2 - In the title 1:1 adduct, C6H6N2O· C11H8O2, the amide group is slightly twisted out of the plane of the aromatic ring, with a C-C-C-N torsion angle of 25.11 (19)°, whereas the carboxylic acid group is approximately coplanar with the bicylic ring system, with a C-C-C-O torsion angle of 10.9 (2)°. The amide groups from two isonicotinamide molecules form a dimer via N-H⋯O hydrogen bonds. In addition, the 2-naphthanoic acid molecule is hydrogen bonded to the pyridine unit of an isonicotinamide molecule via an O-H⋯N hydrogen bond. This gives rise to a centrosymmetric four-molecule chain, which is cross-linked by further N-H⋯O hydrogen bonds from the amide group.

AB - In the title 1:1 adduct, C6H6N2O· C11H8O2, the amide group is slightly twisted out of the plane of the aromatic ring, with a C-C-C-N torsion angle of 25.11 (19)°, whereas the carboxylic acid group is approximately coplanar with the bicylic ring system, with a C-C-C-O torsion angle of 10.9 (2)°. The amide groups from two isonicotinamide molecules form a dimer via N-H⋯O hydrogen bonds. In addition, the 2-naphthanoic acid molecule is hydrogen bonded to the pyridine unit of an isonicotinamide molecule via an O-H⋯N hydrogen bond. This gives rise to a centrosymmetric four-molecule chain, which is cross-linked by further N-H⋯O hydrogen bonds from the amide group.

KW - R factor = 0.041

KW - T = 173 K

KW - data-to-parameter ratio = 12.3

KW - mean σ(C-C) = 0.002 Å

KW - single-crystal X-ray study

KW - wR factor = 0.119

UR - https://www.scopus.com/pages/publications/83155161150

U2 - 10.1107/S1600536811050057

DO - 10.1107/S1600536811050057

M3 - Article

AN - SCOPUS:83155161150

SN - 1600-5368

VL - 67

SP - o3440

JO - Acta Crystallographica Section E: Structure Reports Online

JF - Acta Crystallographica Section E: Structure Reports Online

IS - 12

ER -

Isonicotinamide-2-naphthoic acid (1/1)

Abstract

Keywords

ASJC Scopus subject areas

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