Ethyl 2-(cyclo­pentyl­oxy)-5-ethyl-4-hydroxy-6-methyl­nicotinate

Structural analysis of the title compound, C₁₆H₂₃NO₄, reveals that the pyridine ring and the ester moiety are coplanar. This conformation is stabilized by an intramolecular hydrogen bond between the hydroxyl and ester groups.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.059
• wR factor = 0.185
• Data-to-parameter ratio = 16.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_707  Alert C D...A   Calc    2.517(3), Rep    2.513(3), Dev.      1.33 Sigma
                     O21  -O17     1.555   1.555


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1992); cell refinement: CAD-4 EXPRESS; data reduction: HELENA (Spek, 2000); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97.

ethyl 2-cyclopentoxy-4-hydroxy-5-ethyl-6-methylnicotinate

Crystal data

C16H23NO4	Z = 2
Mr = 293.35	F(000) = 316
Triclinic, P1	Dx = 1.215 Mg m^−3
a = 6.312 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.571 (1) Å	Cell parameters from 25 reflections
c = 12.396 (2) Å	θ = 30.0–40.0°
α = 84.205 (7)°	µ = 0.71 mm^−1
β = 77.098 (8)°	T = 293 K
γ = 88.827 (5)°	Platelet, colourless
V = 802.1 (2) Å^3	0.21 × 0.10 × 0.09 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	1678 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 71.9°, θmin = 3.7°
θ/2θ scans	h = −5→7
Absorption correction: analytical (Alcock, 1970)	k = −13→13
Tmin = 0.865, Tmax = 0.939	l = −14→15
3449 measured reflections	3 standard reflections every 200 reflections
3147 independent reflections	intensity decay: 3.5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.185	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.076P)^2 + 0.272P] where P = (Fo^2 + 2Fc^2)/3
3147 reflections	(Δ/σ)max = 0.023
194 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 (Ų)

	x	y	z	Uiso*/Ueq
O18	0.2799 (3)	0.19478 (17)	0.89384 (16)	0.0597 (5)
O10	0.0536 (3)	0.33292 (16)	0.77986 (18)	0.0715 (6)
O21	−0.0112 (3)	−0.11607 (16)	0.81140 (17)	0.0664 (6)
O17	0.2449 (3)	−0.01468 (18)	0.90672 (18)	0.0730 (6)
N1	−0.1688 (4)	0.2399 (2)	0.68816 (19)	0.0552 (6)
C4	−0.0610 (4)	0.0022 (2)	0.7733 (2)	0.0483 (6)
C16	0.1938 (4)	0.0912 (3)	0.8713 (2)	0.0511 (7)
C3	0.0362 (4)	0.1097 (2)	0.7996 (2)	0.0456 (6)
C2	−0.0294 (4)	0.2274 (2)	0.7535 (2)	0.0510 (7)
C6	−0.2595 (4)	0.1335 (3)	0.6662 (2)	0.0524 (7)
C5	−0.2152 (4)	0.0128 (2)	0.7074 (2)	0.0513 (7)
C19	0.4424 (5)	0.1777 (3)	0.9605 (2)	0.0630 (8)
H19A	0.5662	0.1314	0.9222	0.076*
H19B	0.3817	0.1300	1.0314	0.076*
C8	−0.3176 (5)	−0.1063 (3)	0.6833 (3)	0.0644 (8)
H8A	−0.3393	−0.1673	0.7487	0.077*
H8B	−0.4591	−0.0853	0.6681	0.077*
C7	−0.4164 (5)	0.1593 (3)	0.5912 (3)	0.0727 (9)
H7A	−0.3874	0.1023	0.5340	0.109*
H7B	−0.3994	0.2455	0.5577	0.109*
H7C	−0.5625	0.1465	0.6339	0.109*
C9	−0.1810 (6)	−0.1667 (3)	0.5855 (3)	0.0819 (10)
H9A	−0.1630	−0.1077	0.5199	0.123*
H9B	−0.2521	−0.2421	0.5743	0.123*
H9C	−0.0411	−0.1885	0.6003	0.123*
C12	0.1611 (6)	0.4829 (3)	0.6220 (3)	0.0813 (10)
H12A	0.1093	0.5492	0.5743	0.098*
H12B	0.1878	0.4066	0.5838	0.098*
C11	0.0025 (6)	0.4580 (3)	0.7292 (3)	0.0729 (9)
H11	−0.1482	0.4637	0.7207	0.087*
C13	0.3618 (6)	0.5244 (4)	0.6530 (3)	0.0957 (12)
H13A	0.4526	0.4516	0.6653	0.115*
H13B	0.4443	0.5831	0.5942	0.115*
C15	0.0536 (7)	0.5541 (3)	0.8038 (3)	0.0923 (12)
H15A	−0.0372	0.6290	0.8009	0.111*
H15B	0.0316	0.5170	0.8803	0.111*
C20	0.5104 (6)	0.3063 (3)	0.9781 (3)	0.0900 (11)
H20A	0.5597	0.3548	0.9074	0.135*
H20B	0.6262	0.2987	1.0170	0.135*
H20C	0.3892	0.3486	1.0211	0.135*
C14	0.2913 (7)	0.5872 (4)	0.7560 (4)	0.1093 (14)
H14A	0.3090	0.6785	0.7400	0.131*
H14B	0.3780	0.5577	0.8090	0.131*
H21	0.0969	−0.1024	0.8585	0.113 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O18	0.0603 (12)	0.0564 (11)	0.0703 (13)	−0.0022 (9)	−0.0307 (10)	−0.0062 (9)
O10	0.0845 (15)	0.0415 (10)	0.1017 (16)	−0.0089 (10)	−0.0514 (13)	0.0008 (10)
O21	0.0779 (14)	0.0395 (10)	0.0868 (15)	−0.0010 (9)	−0.0298 (12)	−0.0034 (10)
O17	0.0771 (15)	0.0548 (12)	0.0971 (16)	0.0042 (10)	−0.0452 (13)	0.0017 (11)
N1	0.0546 (14)	0.0477 (13)	0.0676 (15)	−0.0019 (10)	−0.0242 (12)	−0.0021 (11)
C4	0.0484 (16)	0.0397 (14)	0.0549 (16)	−0.0020 (11)	−0.0070 (13)	−0.0058 (12)
C16	0.0472 (16)	0.0494 (15)	0.0580 (17)	−0.0006 (12)	−0.0150 (13)	−0.0042 (13)
C3	0.0420 (15)	0.0446 (14)	0.0511 (15)	−0.0010 (11)	−0.0124 (12)	−0.0046 (11)
C2	0.0490 (16)	0.0424 (14)	0.0645 (17)	−0.0047 (12)	−0.0181 (14)	−0.0062 (12)
C6	0.0455 (16)	0.0586 (16)	0.0548 (16)	−0.0025 (13)	−0.0134 (13)	−0.0080 (13)
C5	0.0477 (16)	0.0517 (16)	0.0550 (17)	−0.0072 (12)	−0.0100 (13)	−0.0099 (13)
C19	0.0541 (18)	0.081 (2)	0.0602 (18)	0.0013 (15)	−0.0255 (15)	−0.0080 (16)
C8	0.0623 (19)	0.0609 (18)	0.073 (2)	−0.0135 (15)	−0.0191 (16)	−0.0104 (15)
C7	0.065 (2)	0.081 (2)	0.082 (2)	−0.0023 (17)	−0.0357 (18)	−0.0087 (18)
C9	0.085 (2)	0.074 (2)	0.095 (3)	−0.0044 (18)	−0.026 (2)	−0.0338 (19)
C12	0.102 (3)	0.067 (2)	0.082 (3)	−0.0008 (19)	−0.034 (2)	−0.0112 (18)
C11	0.071 (2)	0.0489 (17)	0.104 (3)	−0.0037 (15)	−0.034 (2)	0.0008 (16)
C13	0.096 (3)	0.090 (3)	0.103 (3)	−0.024 (2)	−0.023 (2)	−0.012 (2)
C15	0.126 (3)	0.0464 (18)	0.098 (3)	0.0057 (19)	−0.007 (2)	−0.0140 (17)
C20	0.082 (3)	0.104 (3)	0.100 (3)	−0.005 (2)	−0.043 (2)	−0.033 (2)
C14	0.101 (3)	0.102 (3)	0.141 (4)	−0.017 (2)	−0.041 (3)	−0.053 (3)

Geometric parameters (Å, º)

O18—C16	1.314 (3)	C7—H7B	0.9600
O18—C19	1.452 (3)	C7—H7C	0.9600
O10—C2	1.341 (3)	C9—H9A	0.9600
O10—C11	1.468 (3)	C9—H9B	0.9600
O21—C4	1.347 (3)	C9—H9C	0.9600
O21—H21	1.0134	C12—C11	1.477 (5)
O17—C16	1.224 (3)	C12—C13	1.489 (5)
N1—C2	1.319 (3)	C12—H12A	0.9700
N1—C6	1.351 (3)	C12—H12B	0.9700
C4—C5	1.400 (4)	C11—C15	1.525 (5)
C4—C3	1.402 (3)	C11—H11	0.9800
C16—C3	1.473 (4)	C13—C14	1.475 (5)
C3—C2	1.410 (3)	C13—H13A	0.9700
C6—C5	1.374 (4)	C13—H13B	0.9700
C6—C7	1.507 (4)	C15—C14	1.519 (5)
C5—C8	1.512 (3)	C15—H15A	0.9700
C19—C20	1.486 (4)	C15—H15B	0.9700
C19—H19A	0.9700	C20—H20A	0.9600
C19—H19B	0.9700	C20—H20B	0.9600
C8—C9	1.512 (4)	C20—H20C	0.9600
C8—H8A	0.9700	C14—H14A	0.9700
C8—H8B	0.9700	C14—H14B	0.9700
C7—H7A	0.9600
C16—O18—C19	116.8 (2)	C8—C9—H9B	109.5
C2—O10—C11	120.0 (2)	H9A—C9—H9B	109.5
C4—O21—H21	104.4	C8—C9—H9C	109.5
C2—N1—C6	118.1 (2)	H9A—C9—H9C	109.5
O21—C4—C5	117.0 (2)	H9B—C9—H9C	109.5
O21—C4—C3	121.3 (2)	C11—C12—C13	104.5 (3)
C5—C4—C3	121.6 (2)	C11—C12—H12A	110.9
O17—C16—O18	121.6 (2)	C13—C12—H12A	110.9
O17—C16—C3	122.1 (2)	C11—C12—H12B	110.9
O18—C16—C3	116.3 (2)	C13—C12—H12B	110.9
C4—C3—C2	115.4 (2)	H12A—C12—H12B	108.9
C4—C3—C16	118.6 (2)	O10—C11—C12	107.3 (3)
C2—C3—C16	126.0 (2)	O10—C11—C15	105.8 (3)
N1—C2—O10	118.5 (2)	C12—C11—C15	105.9 (3)
N1—C2—C3	124.2 (2)	O10—C11—H11	112.5
O10—C2—C3	117.3 (2)	C12—C11—H11	112.5
N1—C6—C5	124.1 (2)	C15—C11—H11	112.5
N1—C6—C7	113.5 (2)	C14—C13—C12	106.8 (3)
C5—C6—C7	122.4 (2)	C14—C13—H13A	110.4
C6—C5—C4	116.5 (2)	C12—C13—H13A	110.4
C6—C5—C8	124.1 (3)	C14—C13—H13B	110.4
C4—C5—C8	119.4 (2)	C12—C13—H13B	110.4
O18—C19—C20	107.3 (2)	H13A—C13—H13B	108.6
O18—C19—H19A	110.3	C14—C15—C11	104.1 (3)
C20—C19—H19A	110.3	C14—C15—H15A	110.9
O18—C19—H19B	110.3	C11—C15—H15A	110.9
C20—C19—H19B	110.3	C14—C15—H15B	110.9
H19A—C19—H19B	108.5	C11—C15—H15B	110.9
C9—C8—C5	112.8 (2)	H15A—C15—H15B	109.0
C9—C8—H8A	109.0	C19—C20—H20A	109.5
C5—C8—H8A	109.0	C19—C20—H20B	109.5
C9—C8—H8B	109.0	H20A—C20—H20B	109.5
C5—C8—H8B	109.0	C19—C20—H20C	109.5
H8A—C8—H8B	107.8	H20A—C20—H20C	109.5
C6—C7—H7A	109.5	H20B—C20—H20C	109.5
C6—C7—H7B	109.5	C13—C14—C15	107.7 (3)
H7A—C7—H7B	109.5	C13—C14—H14A	110.2
C6—C7—H7C	109.5	C15—C14—H14A	110.2
H7A—C7—H7C	109.5	C13—C14—H14B	110.2
H7B—C7—H7C	109.5	C15—C14—H14B	110.2
C8—C9—H9A	109.5	H14A—C14—H14B	108.5
C19—O18—C16—O17	1.4 (4)	N1—C6—C5—C4	−1.9 (4)
C19—O18—C16—C3	−177.4 (2)	C7—C6—C5—C4	178.0 (3)
O21—C4—C3—C2	179.5 (2)	N1—C6—C5—C8	179.7 (3)
C5—C4—C3—C2	−1.1 (4)	C7—C6—C5—C8	−0.3 (4)
O21—C4—C3—C16	−0.7 (4)	O21—C4—C5—C6	−178.0 (2)
C5—C4—C3—C16	178.7 (2)	C3—C4—C5—C6	2.6 (4)
O17—C16—C3—C4	1.4 (4)	O21—C4—C5—C8	0.4 (4)
O18—C16—C3—C4	−179.8 (2)	C3—C4—C5—C8	−179.0 (2)
O17—C16—C3—C2	−178.8 (3)	C16—O18—C19—C20	−178.2 (3)
O18—C16—C3—C2	0.0 (4)	C6—C5—C8—C9	93.9 (3)
C6—N1—C2—O10	−176.9 (2)	C4—C5—C8—C9	−84.4 (3)
C6—N1—C2—C3	2.0 (4)	C2—O10—C11—C12	−86.2 (3)
C11—O10—C2—N1	−4.8 (4)	C2—O10—C11—C15	161.1 (3)
C11—O10—C2—C3	176.2 (3)	C13—C12—C11—O10	−79.0 (3)
C4—C3—C2—N1	−1.3 (4)	C13—C12—C11—C15	33.6 (4)
C16—C3—C2—N1	178.9 (3)	C11—C12—C13—C14	−29.8 (4)
C4—C3—C2—O10	177.6 (2)	O10—C11—C15—C14	89.2 (3)
C16—C3—C2—O10	−2.2 (4)	C12—C11—C15—C14	−24.5 (4)
C2—N1—C6—C5	−0.3 (4)	C12—C13—C14—C15	14.4 (5)
C2—N1—C6—C7	179.8 (2)	C11—C15—C14—C13	6.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O21—H21···O17	1.01	1.58	2.513 (3)	152
C19—H19A···O17^i	0.97	2.83	3.211 (4)	105

Symmetry code: (i) −x+1, −y, −z+2.