Isonicotinamide–2-naphthoic acid (1/1)

Lee G Madeley; Demetrius C Levendis; Andreas Lemmerer

doi:10.1107/S1600536811050057

. 2011 Nov 25;67(Pt 12):o3440. doi: 10.1107/S1600536811050057

Isonicotinamide–2-naphthoic acid (1/1)

Lee G Madeley ^a, Demetrius C Levendis ^a, Andreas Lemmerer ^a,^*

PMCID: PMC3239073 PMID: 22199921

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.

Related literature

For related compounds, see: Lemmerer et al. (2008 ▶); Aakeröy et al. (2002 ▶); Báthori et al. (2010 ▶). The carboxylic acid–pyridine hydrogen bond is an often used supramolecular synthon, see: Aakeröy & Beatty (2001 ▶).

Experimental

Crystal data

C₆H₆N₂O·C₁₁H₈O₂
M _r = 294.3
Monoclinic,
a = 8.6665 (17) Å
b = 23.752 (5) Å
c = 7.3793 (15) Å
β = 110.33 (3)°
V = 1424.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.48 × 0.45 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: integration (XPREP; Bruker, 2007 ▶) T _min = 0.956, T _max = 0.993
7507 measured reflections
2605 independent reflections
2130 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.119
S = 1.01
2605 reflections
211 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050057/fj2462sup1.cif

e-67-o3440-sup1.cif^{(21.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050057/fj2462Isup2.hkl

e-67-o3440-Isup2.hkl^{(125.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811050057/fj2462Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811050057/fj2462Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1S⋯O1ⁱ	0.904 (19)	2.012 (19)	2.914 (2)	176 (2)
N1—H1A⋯O3ⁱⁱ	0.862 (18)	2.123 (18)	2.9755 (17)	170 (2)
O2—H2⋯N2	1.05 (3)	1.56 (3)	2.5999 (18)	170 (2)

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the University of the Witwatersrand, which is thanked for providing the infrastructure required to do this work.

supplementary crystallographic information

Comment

This co-crystal is part of a larger crystal engineering project involving carboxylic acids and the anti-tuberculosis agent isoniazid. In this project, the pyridine N atom of either nicotinamide, isonicotinamide or isoniazid acts as a hydrogen bond acceptor for carboxylic acid group protons. The carboxylic acid-pyridine hydrogen bond is an often used supramolecular synthon (Aakeröy et al., 2001; Aakeröy et al., 2002; Lemmerer et al., 2008). The co-crystal former ability of isonicotinamide and nicotinamide was investigated by performing density functional theory calculations in a related study (Báthori et al., 2010).

The asymmetric unit of (I) consists of one molecule of isonicotinamide and one molecule of 2-naphthanoic acid, sitting on general positions (Fig. 1). The asymmetric unit is connected by a O—H···N hydrogen bond. The combination of O—H···N and N—H···O hydrogen bonds gives rise to centrosymmetric 4-molecule chains, which are cross-linked by the N—H···O hydrogen bonds (Fig. 2).

Experimental

The compound was prepared by dissolving equimolar amounts of isonicotinamide (0.218 g) and 2-naphthanoic acid (0.308 g) in distilled methanol (15 ml). The mixture was stirred at room temperature under a standard atmosphere for 24 h. Colourless crystals were grown by slow evaporation at ambient conditions from the methanol solvent over a few days.