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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 6| June 2008| Page o971
doi:10.1107/S1600536808007411

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

Wei Daia and Da-Wei Fua*

aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: fudavid88@yahoo.com.cn

(Received 15 March 2008; accepted 18 March 2008; online 3 May 2008)

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[Liu, F.-C., Zeng, Y.-F., Li, J.-R., Bu, X.-H., Zhang, H.-J. & Ribas, J. (2005). Inorg. Chem. 44, 7298-7300.]); Zhao et al. (2007[Zhao, Y.-H., Su, Z.-M., Wang, Y., Fu, Y.-M., Liu, S.-D. & Li, P. (2007). Inorg. Chem. Commun. 10, 410-414.]); He et al. (2005[He, X., Ye, J.-W., Xu, J.-N., Fan, Y., Wang, L., Zhang, P. & Wang, Y. (2005). J. Mol. Struct. 749, 9-12.]); Boovanahalli et al. (2007[Boovanahalli, S. K., Jin, X., Jin, Y., Kim, J. H., Dat, N. T., Hong, Y. S. & Lee, J. H. (2007). Bioorg. Med. Chem. Lett. 17, 6305-6310.]); Song et al. (2006[Song, L., Li, J., Lin, P., Li, Z., Li, T., Du, S.-W. & Wu, X.-T. (2006). Inorg. Chem. 45, 10155-10161.]).

[Scheme 1]

Experimental

Crystal data

  • C15H19N3O3

  • Mr = 289.33

  • Monoclinic, P 21 /c

  • 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[Rigaku (2005). CrystalClear. Version 1.4.0. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.978, Tmax = 0.988

  • 15016 measured reflections

  • 3357 independent reflections

  • 2413 reflections with I > 2σ(I)

  • Rint = 0.045
Refinement

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 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

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
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Version 1.4.0. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]), ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information

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

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

checkCIF report


Comment top

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).

Related literature top

For usages of nicotinic acid and imidazole in coordination chemisty 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 top

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 top

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).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top
[Figure 1] 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
[Figure 2] 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]
(±)-5-Ethyl-2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2- yl)nicotinic acid top
Crystal data top
C15H19N3O3F(000) = 616
Mr = 289.33Dx = 1.297 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2685 reflections
a = 12.6916 (15) Åθ = 3.0–27.5°
b = 16.0748 (17) ŵ = 0.09 mm−1
c = 7.3801 (8) ÅT = 293 K
β = 100.213 (7)°Block, colorless
V = 1481.8 (3) Å30.25 × 0.25 × 0.20 mm
Z = 4
Data collection top
Rigaku Mercury2 (2x2 bin mode)
diffractometer		3357 independent reflections
Radiation source: fine-focus sealed tube2413 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 13.6612 pixels mm-1θmax = 27.4°, θmin = 3.0°
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 top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0611P)2 + 0.3777P]
where P = (Fo2 + 2Fc2)/3
3357 reflections(Δ/σ)max < 0.001
195 parametersΔρmax = 0.20 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C15H19N3O3V = 1481.8 (3) Å3
Mr = 289.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.6916 (15) ŵ = 0.09 mm−1
b = 16.0748 (17) ÅT = 293 K
c = 7.3801 (8) Å0.25 × 0.25 × 0.20 mm
β = 100.213 (7)°
Data collection top
Rigaku Mercury2 (2x2 bin mode)
diffractometer		3357 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)		2413 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.988Rint = 0.045
15016 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.136H-atom parameters constrained
S = 1.03Δρmax = 0.20 e Å−3
3357 reflectionsΔρmin = −0.20 e Å−3
195 parameters
Special details top

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) top
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) top
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, º) top
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, º) top
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 code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC15H19N3O3
Mr289.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.6916 (15), 16.0748 (17), 7.3801 (8)
β (°) 100.213 (7)
V (Å3)1481.8 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.25 × 0.25 × 0.20
Data collection
DiffractometerRigaku Mercury2 (2x2 bin mode)
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.978, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections		15016, 3357, 2413
Rint0.045
(sin θ/λ)max (Å−1)0.647
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.136, 1.03
No. of reflections3357
No. of parameters195
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.20, −0.20

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.682.4984 (18)177.9
N3—H3···O2i0.862.102.9330 (19)161.5
Symmetry code: (i) −x+1, y+1/2, −z+1/2.
 

Acknowledgements

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

References

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ISSN: 2056-9890
Volume 64| Part 6| June 2008| Page o971
doi:10.1107/S1600536808007411
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