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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o971.
Published online 2008 May 3. doi:  10.1107/S1600536808007411
PMCID: PMC2961475

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

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 [triangle]); Zhao et al. (2007 [triangle]); He et al. (2005 [triangle]); Boovanahalli et al. (2007 [triangle]); Song et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o971-scheme1.jpg

Experimental

Crystal data

  • C15H19N3O3
  • M r = 289.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o971-efi2.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.20 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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.

Refinement

All H atoms attached to C, N and O atoms were fixed geometrically and treated as riding with C–H = 0.98 Å (methine), 0.97Å(methylene), 0.96Å (methyl) and N–H= 0.86Å or O–H= 0.82 Å with Uiso(H) = 1.2Ueq(C, N) or Uiso(H) = 1.5Ueq(O, methyl).

Figures

Fig. 1.
Molecular view of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.H bond is shown as dashed line
Fig. 2.
Partial packing view of the title compound sgowing the formation of the chain parallel to the b axis. H bonds are shown as dashed lines. H atoms not involved in hydrogen bondins have been omitted for clarty.[Symmetry code: (i) 1-x, 1/2+y, 1/2-z]

Crystal data

C15H19N3O3F000 = 616
Mr = 289.33Dx = 1.297 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2685 reflections
a = 12.6916 (15) Åθ = 3.0–27.5º
b = 16.0748 (17) ŵ = 0.09 mm1
c = 7.3801 (8) ÅT = 293 (2) K
β = 100.213 (7)ºBlock, colorless
V = 1481.8 (3) Å30.25 × 0.25 × 0.20 mm
Z = 4

Data collection

Rigaku Mercury2 (2x2 bin mode) diffractometer3357 independent reflections
Radiation source: fine-focus sealed tube2413 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.045
Detector resolution: 13.6612 pixels mm-1θmax = 27.4º
T = 293(2) Kθmin = 3.0º
ω scansh = −16→16
Absorption correction: Multi-scan(CrystalClear; Rigaku, 2005)k = −20→20
Tmin = 0.978, Tmax = 0.988l = −9→9
15016 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.136  w = 1/[σ2(Fo2) + (0.0611P)2 + 0.3777P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3357 reflectionsΔρmax = 0.20 e Å3
195 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.56210 (12)0.92867 (8)0.3216 (2)0.0442 (4)
N20.31126 (10)0.86524 (8)0.06785 (19)0.0358 (3)
N30.38168 (11)0.99041 (8)0.1425 (2)0.0419 (4)
H30.42931.02590.19010.050*
O10.36104 (10)0.71477 (7)0.09236 (19)0.0484 (4)
H10.34500.76420.08170.073*
O20.48765 (11)0.63866 (7)0.2486 (2)0.0590 (4)
O30.24362 (11)1.07812 (8)0.0169 (2)0.0626 (4)
C10.65661 (14)0.90689 (11)0.4182 (3)0.0465 (5)
H1A0.70230.94910.47020.056*
C20.69167 (13)0.82543 (11)0.4465 (2)0.0385 (4)
C30.62079 (13)0.76450 (10)0.3712 (2)0.0354 (4)
H3A0.64090.70900.38830.042*
C40.51990 (12)0.78314 (9)0.2704 (2)0.0304 (3)
C50.49432 (12)0.86849 (9)0.2486 (2)0.0328 (4)
C60.39348 (13)0.90513 (9)0.1502 (2)0.0337 (4)
C70.80073 (15)0.80620 (13)0.5550 (3)0.0508 (5)
H7A0.81170.74650.55590.061*
H7B0.80350.82400.68130.061*
C80.89069 (16)0.84795 (14)0.4789 (3)0.0624 (6)
H8A0.88710.83210.35250.094*
H8B0.95830.83090.54920.094*
H8C0.88370.90720.48680.094*
C90.45278 (13)0.70696 (10)0.2013 (2)0.0366 (4)
C100.28196 (14)1.00956 (10)0.0468 (3)0.0429 (4)
C110.22886 (13)0.92565 (10)−0.0124 (2)0.0373 (4)
C120.12537 (15)0.91484 (12)0.0676 (3)0.0492 (5)
H120.07540.95830.01330.059*
C130.0711 (2)0.83164 (17)0.0180 (4)0.0788 (8)
H13A0.11610.78760.07570.118*
H13B0.05920.8244−0.11310.118*
H13C0.00380.83030.06020.118*
C140.1441 (2)0.92685 (19)0.2749 (3)0.0857 (9)
H14A0.07720.92240.31770.128*
H14B0.17450.98090.30500.128*
H14C0.19240.88490.33290.128*
C150.21042 (17)0.91982 (12)−0.2218 (3)0.0527 (5)
H15A0.27700.9283−0.26380.079*
H15B0.16000.9617−0.27370.079*
H15C0.18270.8658−0.25960.079*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0384 (8)0.0285 (7)0.0620 (10)−0.0038 (6)−0.0019 (7)−0.0006 (7)
N20.0334 (8)0.0269 (7)0.0458 (8)0.0002 (5)0.0031 (6)−0.0001 (6)
N30.0331 (8)0.0247 (7)0.0644 (10)−0.0015 (5)−0.0008 (7)−0.0006 (6)
O10.0437 (7)0.0250 (6)0.0718 (9)−0.0017 (5)−0.0033 (6)−0.0029 (6)
O20.0513 (8)0.0237 (6)0.0970 (11)0.0032 (5)−0.0003 (7)0.0047 (6)
O30.0492 (8)0.0285 (7)0.1029 (12)0.0087 (6)−0.0057 (8)0.0011 (7)
C10.0397 (10)0.0354 (9)0.0593 (12)−0.0075 (7)−0.0049 (8)0.0004 (8)
C20.0355 (9)0.0396 (9)0.0395 (9)−0.0003 (7)0.0046 (7)0.0054 (7)
C30.0386 (9)0.0292 (8)0.0400 (9)0.0040 (7)0.0113 (7)0.0051 (7)
C40.0324 (8)0.0261 (7)0.0344 (8)0.0009 (6)0.0105 (6)0.0024 (6)
C50.0317 (8)0.0266 (8)0.0403 (9)−0.0008 (6)0.0072 (7)0.0011 (7)
C60.0349 (9)0.0251 (8)0.0421 (9)−0.0004 (6)0.0091 (7)0.0006 (7)
C70.0420 (10)0.0496 (11)0.0555 (12)0.0018 (8)−0.0059 (9)0.0090 (9)
C80.0375 (11)0.0660 (14)0.0808 (16)0.0043 (9)0.0022 (10)−0.0005 (11)
C90.0375 (9)0.0255 (8)0.0482 (10)0.0001 (7)0.0112 (8)−0.0016 (7)
C100.0386 (10)0.0300 (9)0.0593 (11)0.0029 (7)0.0064 (8)0.0006 (8)
C110.0334 (9)0.0291 (8)0.0476 (10)0.0020 (6)0.0021 (7)0.0004 (7)
C120.0350 (10)0.0503 (11)0.0615 (12)−0.0035 (8)0.0063 (8)−0.0040 (9)
C130.0650 (15)0.0823 (18)0.0907 (19)−0.0356 (13)0.0180 (13)−0.0154 (14)
C140.0713 (17)0.122 (2)0.0717 (17)−0.0306 (15)0.0344 (13)−0.0326 (16)
C150.0595 (13)0.0493 (11)0.0468 (11)0.0068 (9)0.0029 (9)0.0032 (9)

Geometric parameters (Å, °)

N1—C11.329 (2)C7—H7A0.9700
N1—C51.342 (2)C7—H7B0.9700
N2—C61.282 (2)C8—H8A0.9600
N2—C111.472 (2)C8—H8B0.9600
N3—C101.370 (2)C8—H8C0.9600
N3—C61.379 (2)C10—C111.536 (2)
N3—H30.8600C11—C151.524 (3)
O1—C91.298 (2)C11—C121.543 (3)
O1—H10.8200C12—C141.518 (3)
O2—C91.2118 (19)C12—C131.519 (3)
O3—C101.209 (2)C12—H120.9800
C1—C21.387 (2)C13—H13A0.9600
C1—H1A0.9300C13—H13B0.9600
C2—C31.378 (2)C13—H13C0.9600
C2—C71.503 (2)C14—H14A0.9600
C3—C41.395 (2)C14—H14B0.9600
C3—H3A0.9300C14—H14C0.9600
C4—C51.412 (2)C15—H15A0.9600
C4—C91.527 (2)C15—H15B0.9600
C5—C61.477 (2)C15—H15C0.9600
C7—C81.515 (3)
C1—N1—C5118.60 (14)O2—C9—O1120.50 (15)
C6—N2—C11108.73 (13)O2—C9—C4118.47 (15)
C10—N3—C6109.15 (14)O1—C9—C4121.02 (13)
C10—N3—H3125.4O3—C10—N3127.14 (17)
C6—N3—H3125.4O3—C10—C11127.32 (16)
C9—O1—H1109.5N3—C10—C11105.54 (13)
N1—C1—C2124.36 (16)N2—C11—C15109.74 (14)
N1—C1—H1A117.8N2—C11—C10102.72 (13)
C2—C1—H1A117.8C15—C11—C10108.85 (15)
C3—C2—C1116.18 (15)N2—C11—C12111.34 (14)
C3—C2—C7122.83 (16)C15—C11—C12113.15 (15)
C1—C2—C7120.99 (16)C10—C11—C12110.51 (14)
C2—C3—C4122.28 (15)C14—C12—C13109.8 (2)
C2—C3—H3A118.9C14—C12—C11112.33 (16)
C4—C3—H3A118.9C13—C12—C11112.79 (17)
C3—C4—C5116.13 (14)C14—C12—H12107.2
C3—C4—C9114.27 (14)C13—C12—H12107.2
C5—C4—C9129.60 (14)C11—C12—H12107.2
N1—C5—C4122.43 (15)C12—C13—H13A109.5
N1—C5—C6110.34 (13)C12—C13—H13B109.5
C4—C5—C6127.23 (14)H13A—C13—H13B109.5
N2—C6—N3113.84 (14)C12—C13—H13C109.5
N2—C6—C5126.50 (14)H13A—C13—H13C109.5
N3—C6—C5119.66 (14)H13B—C13—H13C109.5
C2—C7—C8113.25 (16)C12—C14—H14A109.5
C2—C7—H7A108.9C12—C14—H14B109.5
C8—C7—H7A108.9H14A—C14—H14B109.5
C2—C7—H7B108.9C12—C14—H14C109.5
C8—C7—H7B108.9H14A—C14—H14C109.5
H7A—C7—H7B107.7H14B—C14—H14C109.5
C7—C8—H8A109.5C11—C15—H15A109.5
C7—C8—H8B109.5C11—C15—H15B109.5
H8A—C8—H8B109.5H15A—C15—H15B109.5
C7—C8—H8C109.5C11—C15—H15C109.5
H8A—C8—H8C109.5H15A—C15—H15C109.5
H8B—C8—H8C109.5H15B—C15—H15C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.682.4984 (18)178
N3—H3···O2i0.862.102.9330 (19)162

Symmetry codes: (i) −x+1, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2325).

References

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  • He, X., Ye, J.-W., Xu, J.-N., Fan, Y., Wang, L., Zhang, P. & Wang, Y. (2005). J. Mol. Struct.749, 9–12.
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