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Abstract top

In the title compound, C₁₅H₁₉N₃O₃, owing to an intramolecular O-HN 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-HO hydrogen bonding, forming an infinite chain parallel to the b axis.

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

Crystal data top

C₁₅H₁₉N₃O₃	F₀₀₀ = 616
M_r = 289.33	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0611P)² + 0.3777P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3357 reflections	Δρ_max = 0.20 e Å⁻³
195 parameters	Δρ_min = −0.20 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Crystal data top

C₁₅H₁₉N₃O₃	V = 1481.8 (3) Å³
M_r = 289.33	Z = 4
Monoclinic, P2₁/c	Mo Kα
a = 12.6916 (15) Å	µ = 0.09 mm⁻¹
b = 16.0748 (17) Å	T = 293 (2) K
c = 7.3801 (8) Å	0.25 × 0.25 × 0.20 mm
β = 100.213 (7)º

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)
T_min = 0.978, T_max = 0.988	R_int = 0.045
15016 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	195 parameters
wR(F²) = 0.136	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
3357 reflections	Δρ_min = −0.20 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, °) top

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

Hydrogen-bond geometry (Å, °) top

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 codes: (i) −x+1, y+1/2, −z+1/2.

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

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 codes: (i) −x+1, y+1/2, −z+1/2.

supplementary materials

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

W. Dai and D.-W. Fu

	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]