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

In the title compound, C(15)H(19)N(3)O(3), owing to an intra-molecular 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 mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonding, forming an infinite chain parallel to the b axis.

Related literature

For usages of nicotinic acid and n class="Chemical">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 = 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

Δρmax = 0.20 e Å−3

Δρmin = −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.

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

C15H19N3O3	F000 = 616
Mr = 289.33	Dx = 1.297 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2685 reflections
a = 12.6916 (15) Å	θ = 3.0–27.5º
b = 16.0748 (17) Å	µ = 0.09 mm−1
c = 7.3801 (8) Å	T = 293 (2) K
β = 100.213 (7)º	Block, colorless
V = 1481.8 (3) Å3	0.25 × 0.25 × 0.20 mm
Z = 4

Rigaku Mercury2 (2x2 bin mode) diffractometer	3357 independent reflections
Radiation source: fine-focus sealed tube	2413 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
Detector resolution: 13.6612 pixels mm-1	θmax = 27.4º
T = 293(2) K	θmin = 3.0º
ω scans	h = −16→16
Absorption correction: Multi-scan(CrystalClear; Rigaku, 2005)	k = −20→20
Tmin = 0.978, Tmax = 0.988	l = −9→9
15016 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-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 reflections	Δρmax = 0.20 e Å−3
195 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
N1	0.56210 (12)	0.92867 (8)	0.3216 (2)	0.0442 (4)
N2	0.31126 (10)	0.86524 (8)	0.06785 (19)	0.0358 (3)
N3	0.38168 (11)	0.99041 (8)	0.1425 (2)	0.0419 (4)
H3	0.4293	1.0259	0.1901	0.050*
O1	0.36104 (10)	0.71477 (7)	0.09236 (19)	0.0484 (4)
H1	0.3450	0.7642	0.0817	0.073*
O2	0.48765 (11)	0.63866 (7)	0.2486 (2)	0.0590 (4)
O3	0.24362 (11)	1.07812 (8)	0.0169 (2)	0.0626 (4)
C1	0.65661 (14)	0.90689 (11)	0.4182 (3)	0.0465 (5)
H1A	0.7023	0.9491	0.4702	0.056*
C2	0.69167 (13)	0.82543 (11)	0.4465 (2)	0.0385 (4)
C3	0.62079 (13)	0.76450 (10)	0.3712 (2)	0.0354 (4)
H3A	0.6409	0.7090	0.3883	0.042*
C4	0.51990 (12)	0.78314 (9)	0.2704 (2)	0.0304 (3)
C5	0.49432 (12)	0.86849 (9)	0.2486 (2)	0.0328 (4)
C6	0.39348 (13)	0.90513 (9)	0.1502 (2)	0.0337 (4)
C7	0.80073 (15)	0.80620 (13)	0.5550 (3)	0.0508 (5)
H7A	0.8117	0.7465	0.5559	0.061*
H7B	0.8035	0.8240	0.6813	0.061*
C8	0.89069 (16)	0.84795 (14)	0.4789 (3)	0.0624 (6)
H8A	0.8871	0.8321	0.3525	0.094*
H8B	0.9583	0.8309	0.5492	0.094*
H8C	0.8837	0.9072	0.4868	0.094*
C9	0.45278 (13)	0.70696 (10)	0.2013 (2)	0.0366 (4)
C10	0.28196 (14)	1.00956 (10)	0.0468 (3)	0.0429 (4)
C11	0.22886 (13)	0.92565 (10)	−0.0124 (2)	0.0373 (4)
C12	0.12537 (15)	0.91484 (12)	0.0676 (3)	0.0492 (5)
H12	0.0754	0.9583	0.0133	0.059*
C13	0.0711 (2)	0.83164 (17)	0.0180 (4)	0.0788 (8)
H13A	0.1161	0.7876	0.0757	0.118*
H13B	0.0592	0.8244	−0.1131	0.118*
H13C	0.0038	0.8303	0.0602	0.118*
C14	0.1441 (2)	0.92685 (19)	0.2749 (3)	0.0857 (9)
H14A	0.0772	0.9224	0.3177	0.128*
H14B	0.1745	0.9809	0.3050	0.128*
H14C	0.1924	0.8849	0.3329	0.128*
C15	0.21042 (17)	0.91982 (12)	−0.2218 (3)	0.0527 (5)
H15A	0.2770	0.9283	−0.2638	0.079*
H15B	0.1600	0.9617	−0.2737	0.079*
H15C	0.1827	0.8658	−0.2596	0.079*

	U11	U22	U33	U12	U13	U23
N1	0.0384 (8)	0.0285 (7)	0.0620 (10)	−0.0038 (6)	−0.0019 (7)	−0.0006 (7)
N2	0.0334 (8)	0.0269 (7)	0.0458 (8)	0.0002 (5)	0.0031 (6)	−0.0001 (6)
N3	0.0331 (8)	0.0247 (7)	0.0644 (10)	−0.0015 (5)	−0.0008 (7)	−0.0006 (6)
O1	0.0437 (7)	0.0250 (6)	0.0718 (9)	−0.0017 (5)	−0.0033 (6)	−0.0029 (6)
O2	0.0513 (8)	0.0237 (6)	0.0970 (11)	0.0032 (5)	−0.0003 (7)	0.0047 (6)
O3	0.0492 (8)	0.0285 (7)	0.1029 (12)	0.0087 (6)	−0.0057 (8)	0.0011 (7)
C1	0.0397 (10)	0.0354 (9)	0.0593 (12)	−0.0075 (7)	−0.0049 (8)	0.0004 (8)
C2	0.0355 (9)	0.0396 (9)	0.0395 (9)	−0.0003 (7)	0.0046 (7)	0.0054 (7)
C3	0.0386 (9)	0.0292 (8)	0.0400 (9)	0.0040 (7)	0.0113 (7)	0.0051 (7)
C4	0.0324 (8)	0.0261 (7)	0.0344 (8)	0.0009 (6)	0.0105 (6)	0.0024 (6)
C5	0.0317 (8)	0.0266 (8)	0.0403 (9)	−0.0008 (6)	0.0072 (7)	0.0011 (7)
C6	0.0349 (9)	0.0251 (8)	0.0421 (9)	−0.0004 (6)	0.0091 (7)	0.0006 (7)
C7	0.0420 (10)	0.0496 (11)	0.0555 (12)	0.0018 (8)	−0.0059 (9)	0.0090 (9)
C8	0.0375 (11)	0.0660 (14)	0.0808 (16)	0.0043 (9)	0.0022 (10)	−0.0005 (11)
C9	0.0375 (9)	0.0255 (8)	0.0482 (10)	0.0001 (7)	0.0112 (8)	−0.0016 (7)
C10	0.0386 (10)	0.0300 (9)	0.0593 (11)	0.0029 (7)	0.0064 (8)	0.0006 (8)
C11	0.0334 (9)	0.0291 (8)	0.0476 (10)	0.0020 (6)	0.0021 (7)	0.0004 (7)
C12	0.0350 (10)	0.0503 (11)	0.0615 (12)	−0.0035 (8)	0.0063 (8)	−0.0040 (9)
C13	0.0650 (15)	0.0823 (18)	0.0907 (19)	−0.0356 (13)	0.0180 (13)	−0.0154 (14)
C14	0.0713 (17)	0.122 (2)	0.0717 (17)	−0.0306 (15)	0.0344 (13)	−0.0326 (16)
C15	0.0595 (13)	0.0493 (11)	0.0468 (11)	0.0068 (9)	0.0029 (9)	0.0032 (9)

N1—C1	1.329 (2)	C7—H7A	0.9700
N1—C5	1.342 (2)	C7—H7B	0.9700
N2—C6	1.282 (2)	C8—H8A	0.9600
N2—C11	1.472 (2)	C8—H8B	0.9600
N3—C10	1.370 (2)	C8—H8C	0.9600
N3—C6	1.379 (2)	C10—C11	1.536 (2)
N3—H3	0.8600	C11—C15	1.524 (3)
O1—C9	1.298 (2)	C11—C12	1.543 (3)
O1—H1	0.8200	C12—C14	1.518 (3)
O2—C9	1.2118 (19)	C12—C13	1.519 (3)
O3—C10	1.209 (2)	C12—H12	0.9800
C1—C2	1.387 (2)	C13—H13A	0.9600
C1—H1A	0.9300	C13—H13B	0.9600
C2—C3	1.378 (2)	C13—H13C	0.9600
C2—C7	1.503 (2)	C14—H14A	0.9600
C3—C4	1.395 (2)	C14—H14B	0.9600
C3—H3A	0.9300	C14—H14C	0.9600
C4—C5	1.412 (2)	C15—H15A	0.9600
C4—C9	1.527 (2)	C15—H15B	0.9600
C5—C6	1.477 (2)	C15—H15C	0.9600
C7—C8	1.515 (3)
C1—N1—C5	118.60 (14)	O2—C9—O1	120.50 (15)
C6—N2—C11	108.73 (13)	O2—C9—C4	118.47 (15)
C10—N3—C6	109.15 (14)	O1—C9—C4	121.02 (13)
C10—N3—H3	125.4	O3—C10—N3	127.14 (17)
C6—N3—H3	125.4	O3—C10—C11	127.32 (16)
C9—O1—H1	109.5	N3—C10—C11	105.54 (13)
N1—C1—C2	124.36 (16)	N2—C11—C15	109.74 (14)
N1—C1—H1A	117.8	N2—C11—C10	102.72 (13)
C2—C1—H1A	117.8	C15—C11—C10	108.85 (15)
C3—C2—C1	116.18 (15)	N2—C11—C12	111.34 (14)
C3—C2—C7	122.83 (16)	C15—C11—C12	113.15 (15)
C1—C2—C7	120.99 (16)	C10—C11—C12	110.51 (14)
C2—C3—C4	122.28 (15)	C14—C12—C13	109.8 (2)
C2—C3—H3A	118.9	C14—C12—C11	112.33 (16)
C4—C3—H3A	118.9	C13—C12—C11	112.79 (17)
C3—C4—C5	116.13 (14)	C14—C12—H12	107.2
C3—C4—C9	114.27 (14)	C13—C12—H12	107.2
C5—C4—C9	129.60 (14)	C11—C12—H12	107.2
N1—C5—C4	122.43 (15)	C12—C13—H13A	109.5
N1—C5—C6	110.34 (13)	C12—C13—H13B	109.5
C4—C5—C6	127.23 (14)	H13A—C13—H13B	109.5
N2—C6—N3	113.84 (14)	C12—C13—H13C	109.5
N2—C6—C5	126.50 (14)	H13A—C13—H13C	109.5
N3—C6—C5	119.66 (14)	H13B—C13—H13C	109.5
C2—C7—C8	113.25 (16)	C12—C14—H14A	109.5
C2—C7—H7A	108.9	C12—C14—H14B	109.5
C8—C7—H7A	108.9	H14A—C14—H14B	109.5
C2—C7—H7B	108.9	C12—C14—H14C	109.5
C8—C7—H7B	108.9	H14A—C14—H14C	109.5
H7A—C7—H7B	107.7	H14B—C14—H14C	109.5
C7—C8—H8A	109.5	C11—C15—H15A	109.5
C7—C8—H8B	109.5	C11—C15—H15B	109.5
H8A—C8—H8B	109.5	H15A—C15—H15B	109.5
C7—C8—H8C	109.5	C11—C15—H15C	109.5
H8A—C8—H8C	109.5	H15A—C15—H15C	109.5
H8B—C8—H8C	109.5	H15B—C15—H15C	109.5

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

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) .