(±)-5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid

Wei Dai; Da-Wei Fu

doi:10.1107/S1600536808007411

. 2008 May 3;64(Pt 6):o971. doi: 10.1107/S1600536808007411

(±)-5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid

Wei Dai ^a, Da-Wei Fu ^a,^*

PMCID: PMC2961475 PMID: 21202700

Abstract

In the title compound, C₁₅H₁₉N₃O₃, owing to an intramolecular O—H⋯N hydrogen bond, the pyridine and imidazole rings are nearly coplanar and are twisted from each other by a dihedral angle of only 0.92 (9)°. The molecules are linked through intermolecular N—H⋯O hydrogen bonding, forming an infinite chain parallel to the b axis.

Related literature

For usages of nicotinic acid and imidazole in coordination chemistry and medicinal chemistry, see: Liu et al. (2005 ▶); Zhao et al. (2007 ▶); He et al. (2005 ▶); Boovanahalli et al. (2007 ▶); Song et al. (2006 ▶).

Experimental

Crystal data

C₁₅H₁₉N₃O₃
M _r = 289.33
Monoclinic,
a = 12.6916 (15) Å
b = 16.0748 (17) Å
c = 7.3801 (8) Å
β = 100.213 (7)°
V = 1481.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.25 × 0.25 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.978, T _max = 0.988
15016 measured reflections
3357 independent reflections
2413 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.136
S = 1.03
3357 reflections
195 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007411/dn2325sup1.cif

e-64-0o971-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007411/dn2325Isup2.hkl

e-64-0o971-Isup2.hkl^{(164.7KB, hkl)}

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
O1—H1⋯N2	0.82	1.68	2.4984 (18)	178
N3—H3⋯O2ⁱ	0.86	2.10	2.9330 (19)	162

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by a Start-up Grant from Southeast University to Professor Ren-Gen Xiong.

supplementary crystallographic information

Comment

The nicotinic acid and the imidazole group have found a wide range of applications in coordination chemistry as ligands, in medicinal chemistry and materials science (Liu et al. 2005; Zhao et al. 2007;He et al. 2005; Boovanahalli et al. 2007; Song et al. 2006). We report here the crystal structure of the title compound, C₁₅H₁₉N₃O₃.

Owing to an intramolecular O1-H1···N2 hydrogen, the pyridine and the imidazole rings are nearly planar, they are only twisted to each other by a dihedral angle of 0.91 (9) . In the imidazole ring, the C6=N2 bond distance of 1.282 (4) Å conforms to the value for a double bond, while the C11—N2 bond length of 1.472 (4) Å conforms to the value for a single bond. To the carboxyl group, the C9=O2 bond distance of 1.212 (4) Å conforms to the value for a double bond, while the C9—O1 bond length of 1.298 (4) Å conforms to the value for a single bond.

The molecules are linked through intermolecular N3-H3···O2 hydrogen bond forming an infinite chain parallel to the b axis. (Table 1 and Fig. 2).

Experimental

5-ethyl-2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid (3 mmol) was dissolved in ethanol (20 ml) and evaporated in the air affording colorless block crystals of this compound suitable for X-ray analysis were obtained.