tert-Butyl 2-(3-acetyl-amino-2-oxo-1,2-dihydro-1-pyrid-yl)acetate.

The title compound, C(13)H(18)N(2)O(4), crystallizes as discrete mol-ecules associated as N-H⋯O hydrogen-bonded dimers disposed about a crystallographic inversion centre. The structure is the first solid-state structure for a 3-acetyl-pyridone without C-4 to C-6 substituents. The amide subsituent at C-3 is coplanar with the pyridone ring, while the tert-butyl ester group is orthogonal to the pyridine ring. The amide and ester carbonyl O atoms are not involved in strong hydrogen bonding with only a number of intramolecular and intermolecular C-H⋯O inter-actions apparent in the structure.

Related literature

For general background, see: Bernstein et al. (1994 ▶); Dragovich et al. (2002 ▶); Hu et al. (2008 ▶); Karis et al. (2007 ▶); Kim et al. (2008 ▶); Loughlin et al. (2004 ▶); Reiner et al. (1999 ▶); Semple et al. (1998 ▶); Veale et al. (1995 ▶). For the synthesis, see: Sanderson et al. (1997 ▶); Tamura et al. (1996 ▶). For related structures. see: Karis et al. (2006 ▶); Yang & Craven (1998 ▶).

Experimental

Crystal data

C13H18N2O4

M = 266.29

Monoclinic,

a = 13.9417 (15) Å

b = 5.585 (1) Å

c = 17.861 (2) Å

β = 97.039 (9)°

V = 1380.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 (2) K

0.40 × 0.30 × 0.20 mm

Data collection

Rigaku AFC-7R diffractometer

Absorption correction: none

2731 measured reflections

2428 independent reflections

1482 reflections with I > 2σ(I)

R int = 0.046

3 standard reflections every 150 reflections intensity decay: 0.6%

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.162

S = 1.02

2428 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

Data collection: MSC/AFC7 Diffractometer Control Software (Molecular Structure Corporation, 1999 ▶); cell refinement: MSC/AFC7 Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001 ▶); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039810/bt2816sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039810/bt2816Isup2.hkl

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

C13H18N2O4	F000 = 568
Mr = 266.29	Dx = 1.281 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 13.9417 (15) Å	θ = 12.6–17.5º
b = 5.585 (1) Å	µ = 0.10 mm−1
c = 17.861 (2) Å	T = 295 (2) K
β = 97.039 (9)º	Block, red
V = 1380.3 (3) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Rigaku AFC-7R diffractometer	Rint = 0.046
Radiation source: Rigaku rotating anode	θmax = 25.0º
Monochromator: graphite	θmin = 2.6º
T = 295 K	h = −16→16
ω–2θ scans	k = −6→0
Absorption correction: none	l = −21→10
2731 measured reflections	3 standard reflections
2428 independent reflections	every 150 reflections
1482 reflections with I > 2σ(I)	intensity decay: 0.6%

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.0906P)2 + 0.0473P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
2428 reflections	Δρmax = 0.27 e Å−3
176 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The scan width was (1.79 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O2	0.93631 (11)	0.2790 (3)	0.03272 (10)	0.0595 (6)
O3	1.26910 (13)	0.2449 (4)	0.15628 (14)	0.0940 (9)
O11	0.79117 (14)	0.2673 (4)	0.16249 (13)	0.0868 (9)
O12	0.66171 (11)	0.0894 (3)	0.09995 (9)	0.0520 (6)
N1	0.91347 (13)	−0.0488 (3)	0.10449 (11)	0.0487 (6)
N3	1.12376 (12)	0.3204 (4)	0.08928 (11)	0.0497 (7)
C2	0.97001 (15)	0.1321 (4)	0.08098 (12)	0.0450 (7)
C3	1.06936 (15)	0.1361 (4)	0.11623 (12)	0.0450 (7)
C4	1.10110 (17)	−0.0279 (5)	0.16998 (14)	0.0546 (8)
C5	1.0390 (2)	−0.2076 (5)	0.19027 (15)	0.0634 (10)
C6	0.94768 (18)	−0.2158 (5)	0.15792 (15)	0.0580 (9)
C11	0.81146 (16)	−0.0501 (4)	0.07545 (14)	0.0508 (8)
C12	0.75508 (16)	0.1222 (4)	0.11859 (14)	0.0505 (8)
C13	0.58947 (17)	0.2243 (5)	0.13832 (15)	0.0569 (9)
C14	0.4945 (2)	0.1252 (7)	0.1020 (2)	0.0982 (15)
C15	0.6042 (2)	0.1659 (8)	0.22108 (18)	0.0934 (14)
C16	0.5968 (3)	0.4858 (6)	0.1224 (3)	0.1150 (18)
C31	1.21909 (17)	0.3673 (5)	0.11050 (15)	0.0577 (9)
C32	1.25913 (17)	0.5768 (6)	0.07310 (16)	0.0683 (10)
H3	1.09400	0.41360	0.05580	0.0590*
H4	1.16570	−0.02040	0.19410	0.0650*
H5	1.06240	−0.32280	0.22700	0.0750*
H6	0.90590	−0.33820	0.17180	0.0690*
H14A	0.44270	0.19330	0.12570	0.1480*
H14B	0.49430	−0.04570	0.10780	0.1480*
H14C	0.48610	0.16470	0.04930	0.1480*
H15A	0.66300	0.23860	0.24400	0.1400*
H15B	0.60820	−0.00460	0.22760	0.1400*
H15C	0.55080	0.22640	0.24460	0.1400*
H16A	0.65600	0.54750	0.14840	0.1730*
H16B	0.54300	0.56810	0.13940	0.1730*
H16C	0.59610	0.50990	0.06910	0.1730*
H32A	1.31990	0.53370	0.05670	0.1030*
H32B	1.26860	0.70740	0.10820	0.1030*
H32C	1.21470	0.62420	0.03030	0.1030*
H111	0.78650	−0.20760	0.07980	0.0610*
H112	0.80430	−0.00530	0.02370	0.0610*

	U11	U22	U33	U12	U13	U23
O2	0.0418 (9)	0.0716 (12)	0.0638 (10)	−0.0042 (9)	0.0008 (8)	0.0138 (10)
O3	0.0447 (10)	0.1068 (17)	0.1239 (19)	−0.0035 (11)	−0.0167 (11)	0.0397 (15)
O11	0.0571 (12)	0.0988 (16)	0.1066 (16)	−0.0158 (11)	0.0190 (11)	−0.0554 (14)
O12	0.0417 (9)	0.0507 (10)	0.0646 (10)	0.0020 (7)	0.0110 (7)	−0.0070 (9)
N1	0.0405 (10)	0.0493 (11)	0.0577 (12)	−0.0012 (9)	0.0119 (9)	−0.0033 (10)
N3	0.0332 (10)	0.0621 (13)	0.0531 (11)	0.0032 (9)	0.0028 (8)	0.0019 (10)
C2	0.0375 (11)	0.0517 (14)	0.0468 (12)	0.0008 (11)	0.0096 (10)	−0.0036 (12)
C3	0.0375 (11)	0.0528 (14)	0.0461 (12)	0.0056 (10)	0.0111 (10)	−0.0059 (11)
C4	0.0445 (13)	0.0635 (16)	0.0555 (14)	0.0082 (12)	0.0052 (11)	−0.0015 (13)
C5	0.0629 (16)	0.0598 (17)	0.0673 (17)	0.0109 (14)	0.0076 (13)	0.0107 (14)
C6	0.0583 (15)	0.0487 (15)	0.0680 (16)	0.0000 (12)	0.0118 (13)	0.0020 (13)
C11	0.0404 (12)	0.0517 (14)	0.0614 (14)	−0.0088 (11)	0.0112 (11)	−0.0087 (12)
C12	0.0421 (13)	0.0530 (14)	0.0575 (14)	−0.0060 (11)	0.0100 (11)	−0.0062 (12)
C13	0.0495 (14)	0.0502 (15)	0.0751 (17)	0.0081 (11)	0.0243 (12)	0.0020 (13)
C14	0.0472 (16)	0.105 (3)	0.142 (3)	0.0181 (17)	0.0101 (18)	−0.018 (2)
C15	0.083 (2)	0.122 (3)	0.083 (2)	0.014 (2)	0.0411 (18)	0.010 (2)
C16	0.127 (3)	0.0546 (19)	0.180 (4)	0.024 (2)	0.085 (3)	0.024 (2)
C31	0.0377 (13)	0.0680 (17)	0.0671 (16)	0.0021 (12)	0.0049 (12)	−0.0023 (14)
C32	0.0407 (13)	0.081 (2)	0.0817 (19)	−0.0074 (13)	0.0020 (13)	0.0100 (16)

O2—C2	1.240 (3)	C31—C32	1.489 (4)
O3—C31	1.218 (3)	C4—H4	0.9500
O11—C12	1.195 (3)	C5—H5	0.9500
O12—C12	1.316 (3)	C6—H6	0.9500
O12—C13	1.490 (3)	C11—H111	0.9500
N1—C2	1.378 (3)	C11—H112	0.9500
N1—C6	1.377 (3)	C14—H14A	0.9600
N1—C11	1.453 (3)	C14—H14B	0.9600
N3—C3	1.399 (3)	C14—H14C	0.9600
N3—C31	1.362 (3)	C15—H15A	0.9600
N3—H3	0.8600	C15—H15B	0.9600
C2—C3	1.450 (3)	C15—H15C	0.9600
C3—C4	1.361 (3)	C16—H16A	0.9600
C4—C5	1.402 (4)	C16—H16B	0.9600
C5—C6	1.333 (4)	C16—H16C	0.9600
C11—C12	1.512 (3)	C32—H32A	0.9600
C13—C14	1.507 (4)	C32—H32B	0.9600
C13—C16	1.494 (4)	C32—H32C	0.9600
C13—C15	1.503 (4)
O2···N3	2.694 (2)	C31···H4	2.7800
O2···C12	3.233 (3)	C32···H112i	3.0200
O2···C32i	3.222 (3)	H3···O2	2.3100
O2···N3i	3.164 (3)	H3···H32C	2.1500
O3···C4	2.830 (3)	H3···O2i	2.3400
O11···C2	3.130 (3)	H4···O3	2.2300
O11···N1	2.744 (3)	H4···C31	2.7800
O11···C15	2.980 (4)	H4···O11vi	2.8200
O11···C16	2.978 (5)	H5···O11vi	2.7100
O11···C5ii	3.319 (4)	H5···C5vi	3.0500
O11···C4ii	3.379 (3)	H5···C6vi	3.0200
O2···H3	2.3100	H6···O11vii	2.7200
O2···H32Ci	2.3300	H6···H111	2.3100
O2···H112	2.4200	H6···C4vi	3.0300
O2···H3i	2.3400	H14A···O3viii	2.5600
O3···H4	2.2300	H14A···H15C	2.4600
O3···H14Aiii	2.5600	H14A···H16B	2.5100
O3···H15Bii	2.8800	H14B···C16vii	2.9800
O11···H16A	2.4400	H14B···H15B	2.5100
O11···H6iv	2.7200	H14B···H16Bvii	2.3100
O11···H15A	2.4400	H14C···H16C	2.4600
O11···H4ii	2.8200	H15A···O11	2.4400
O11···H5ii	2.7100	H15A···C12	2.7900
N1···O11	2.744 (3)	H15A···H16A	2.4200
N3···O2	2.694 (2)	H15B···C12	3.0800
N3···O2i	3.164 (3)	H15B···H14B	2.5100
N3···H112v	2.9400	H15B···O3vi	2.8800
C2···O11	3.130 (3)	H15C···H14A	2.4600
C2···C2v	3.441 (3)	H16A···O11	2.4400
C4···O3	2.830 (3)	H16A···C12	2.8300
C4···O11vi	3.379 (3)	H16A···H15A	2.4200
C5···O11vi	3.319 (4)	H16B···H14A	2.5100
C12···O2	3.233 (3)	H16B···H14Biv	2.3100
C15···O11	2.980 (4)	H16C···H14C	2.4600
C16···O11	2.978 (5)	H32B···C4iv	3.0800
C32···O2i	3.222 (3)	H32C···H3	2.1500
C4···H32Bvii	3.0800	H32C···O2i	2.3300
C4···H6ii	3.0300	H32C···C11i	3.0300
C5···H5ii	3.0500	H32C···C12i	3.0900
C6···H5ii	3.0200	H32C···H112i	2.3400
C11···H32Ci	3.0300	H111···H6	2.3100
C12···H15A	2.7900	H112···O2	2.4200
C12···H32Ci	3.0900	H112···N3v	2.9400
C12···H16A	2.8300	H112···C32i	3.0200
C12···H15B	3.0800	H112···H32Ci	2.3400
C16···H14Biv	2.9800
C12—O12—C13	121.10 (18)	C6—C5—H5	120.00
C2—N1—C6	123.04 (19)	N1—C6—H6	120.00
C2—N1—C11	117.79 (18)	C5—C6—H6	120.00
C6—N1—C11	119.00 (19)	N1—C11—H111	109.00
C3—N3—C31	126.7 (2)	N1—C11—H112	109.00
C3—N3—H3	117.00	C12—C11—H111	109.00
C31—N3—H3	117.00	C12—C11—H112	109.00
N1—C2—C3	115.51 (19)	H111—C11—H112	109.00
O2—C2—N1	120.98 (19)	C13—C14—H14A	109.00
O2—C2—C3	123.5 (2)	C13—C14—H14B	109.00
N3—C3—C2	113.04 (19)	C13—C14—H14C	109.00
N3—C3—C4	126.5 (2)	H14A—C14—H14B	110.00
C2—C3—C4	120.5 (2)	H14A—C14—H14C	109.00
C3—C4—C5	120.4 (2)	H14B—C14—H14C	109.00
C4—C5—C6	120.0 (3)	C13—C15—H15A	110.00
N1—C6—C5	120.6 (2)	C13—C15—H15B	109.00
N1—C11—C12	111.23 (19)	C13—C15—H15C	110.00
O11—C12—C11	124.2 (2)	H15A—C15—H15B	109.00
O11—C12—O12	125.7 (2)	H15A—C15—H15C	109.00
O12—C12—C11	110.02 (19)	H15B—C15—H15C	109.00
O12—C13—C15	108.9 (2)	C13—C16—H16A	109.00
O12—C13—C14	103.0 (2)	C13—C16—H16B	109.00
C14—C13—C16	110.8 (3)	C13—C16—H16C	109.00
C15—C13—C16	113.3 (3)	H16A—C16—H16B	109.00
O12—C13—C16	109.9 (2)	H16A—C16—H16C	109.00
C14—C13—C15	110.5 (2)	H16B—C16—H16C	109.00
N3—C31—C32	115.7 (2)	C31—C32—H32A	109.00
O3—C31—N3	122.5 (2)	C31—C32—H32B	109.00
O3—C31—C32	121.8 (2)	C31—C32—H32C	109.00
C3—C4—H4	120.00	H32A—C32—H32B	109.00
C5—C4—H4	120.00	H32A—C32—H32C	109.00
C4—C5—H5	120.00	H32B—C32—H32C	110.00
C13—O12—C12—O11	−5.0 (4)	C31—N3—C3—C4	1.5 (4)
C13—O12—C12—C11	175.59 (19)	C3—N3—C31—O3	1.4 (4)
C12—O12—C13—C14	−177.9 (2)	C3—N3—C31—C32	−179.6 (2)
C12—O12—C13—C15	−60.6 (3)	O2—C2—C3—N3	−1.0 (3)
C12—O12—C13—C16	64.0 (3)	O2—C2—C3—C4	178.7 (2)
C6—N1—C2—O2	−180.0 (2)	N1—C2—C3—N3	178.89 (19)
C6—N1—C2—C3	0.2 (3)	N1—C2—C3—C4	−1.4 (3)
C11—N1—C2—O2	−4.9 (3)	N3—C3—C4—C5	−178.3 (2)
C11—N1—C2—C3	175.25 (19)	C2—C3—C4—C5	2.0 (4)
C2—N1—C6—C5	0.6 (4)	C3—C4—C5—C6	−1.3 (4)
C11—N1—C6—C5	−174.5 (2)	C4—C5—C6—N1	0.0 (4)
C2—N1—C11—C12	−81.1 (2)	N1—C11—C12—O11	11.0 (3)
C6—N1—C11—C12	94.2 (2)	N1—C11—C12—O12	−169.61 (18)
C31—N3—C3—C2	−178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2i	0.8600	2.3400	3.164 (3)	161.00
C4—H4···O3	0.9500	2.2300	2.830 (3)	120.00
C14—H14A···O3viii	0.96	2.56	3.465 (4)	157
C15—H15A···O11	0.96	2.44	2.980 (4)	115
C16—H16A···O11	0.96	2.44	2.978 (5)	115
C32—H32C···O2i	0.96	2.33	3.222 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2i	0.86	2.34	3.164 (3)	161
C4—H4⋯O3	0.95	2.23	2.830 (3)	120
C14—H14A⋯O3ii	0.96	2.56	3.465 (4)	157
C15—H15A⋯O11	0.96	2.44	2.980 (4)	115
C16—H16A⋯O11	0.96	2.44	2.978 (5)	115
C32—H32C⋯O2i	0.96	2.33	3.222 (3)	155

Symmetry codes: (i) ; (ii) .