3-Ethyl-4-hy-droxy-8-meth-oxy-quinolin-2(1H)-one.

In the title compound, C(12)H(13)NO(3), the quinoline ring system is approximately planar with a maximum deviation from the least-squares plane of 0.058 (2) Å. In the crystal, N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into chains running along the b-axis direction. The chains also feature π-π inter-actions between pyridine and benzene rings of inversion-related mol-ecules [centroid-centroid distance = 3.609 (2) Å].

Related literature

For naturally occurring 3-alkyl-4-hy­droxy­quinolin-2-ones, see: Paul & Bose (1968 ▶); Faizutdinova et al. (1969 ▶); Jurd et al. (1983 ▶); Chen et al. (1994 ▶); Yamamoto & Harimaya (2004 ▶); Jain et al. (2006 ▶). For the first published synthesis of the title compound, see: Rapoport & Holden (1959 ▶). For recent synthetic utilization of 3-alkyl-4-hy­droxy­quinolin-2-ones, see, for example: Kimmel et al. (2010 ▶).

Experimental

Crystal data

C12H13NO3

M = 219.23

Monoclinic,

a = 11.4824 (4) Å

b = 6.9072 (2) Å

c = 14.4978 (5) Å

β = 113.1283 (15)°

V = 1057.42 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.35 × 0.25 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.966, T max = 0.992

4558 measured reflections

2403 independent reflections

1734 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.272

S = 1.14

2403 reflections

151 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.29 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812043279/tk5161sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043279/tk5161Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043279/tk5161Isup3.cml

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

C12H13NO3	F(000) = 464
Mr = 219.23	Dx = 1.377 Mg m−3
Monoclinic, P21/c	Melting point = 496–498 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.4824 (4) Å	Cell parameters from 2554 reflections
b = 6.9072 (2) Å	θ = 0.4–27.5°
c = 14.4978 (5) Å	µ = 0.10 mm−1
β = 113.1283 (15)°	T = 293 K
V = 1057.42 (6) Å3	Prism, colourless
Z = 4	0.35 × 0.25 × 0.08 mm

Nonius KappaCCD area-detector diffractometer	2403 independent reflections
Radiation source: fine-focus sealed tube	1734 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ scans + ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −14→14
Tmin = 0.966, Tmax = 0.992	k = −8→8
4558 measured reflections	l = −18→18

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.272	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ2(Fo2) + (0.1076P)2 + 1.7454P] where P = (Fo2 + 2Fc2)/3
2403 reflections	(Δ/σ)max = 0.0001
151 parameters	Δρmax = 0.37 e Å−3
1 restraint	Δρmin = −0.29 e Å−3

Experimental. 279 frames in 4 sets of φ scans + ω scans. Rotation/frame = 1.6 °. Crystal-detector distance = 32 mm. Measuring time = 150 s/°.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.0025 (3)	0.7822 (4)	0.0870 (2)	0.0373 (7)
H1N	−0.045 (3)	0.880 (4)	0.064 (3)	0.045*
O1	0.1611 (2)	0.9727 (3)	0.0836 (2)	0.0482 (7)
O2	0.2406 (2)	0.3155 (4)	0.1696 (2)	0.0506 (7)
H2	0.1991	0.2151	0.1570	0.076*
O3	−0.2344 (2)	0.7758 (4)	0.0700 (2)	0.0584 (8)
C1	0.1260 (3)	0.8088 (5)	0.1009 (3)	0.0362 (7)
C2	0.2089 (3)	0.6432 (5)	0.1318 (3)	0.0370 (8)
C3	0.3448 (3)	0.6709 (6)	0.1462 (3)	0.0437 (9)
H3A	0.3497	0.7733	0.1020	0.052*
H3B	0.3757	0.5528	0.1275	0.052*
C4	0.4286 (4)	0.7222 (9)	0.2532 (4)	0.0740 (15)
H4A	0.4028	0.8447	0.2702	0.111*
H4B	0.5150	0.7303	0.2599	0.111*
H4C	0.4212	0.6241	0.2975	0.111*
C5	0.1612 (3)	0.4696 (5)	0.1440 (2)	0.0359 (7)
C6	0.0321 (3)	0.4481 (5)	0.1348 (2)	0.0356 (7)
C7	−0.0181 (3)	0.2749 (5)	0.1554 (3)	0.0407 (8)
H7	0.0325	0.1651	0.1758	0.049*
C8	−0.1418 (4)	0.2694 (6)	0.1450 (3)	0.0473 (9)
H8	−0.1749	0.1547	0.1580	0.057*
C9	−0.2195 (3)	0.4337 (6)	0.1151 (3)	0.0469 (9)
H9	−0.3035	0.4269	0.1080	0.056*
C10	−0.1721 (3)	0.6033 (6)	0.0964 (3)	0.0412 (8)
C11	−0.0451 (3)	0.6117 (5)	0.1052 (2)	0.0353 (7)
C12	−0.3645 (4)	0.7815 (8)	0.0518 (4)	0.0780 (16)
H12A	−0.4091	0.6864	0.0022	0.117*
H12B	−0.3977	0.9078	0.0281	0.117*
H12C	−0.3753	0.7540	0.1129	0.117*

	U11	U22	U33	U12	U13	U23
N1	0.0334 (14)	0.0319 (14)	0.0455 (16)	0.0049 (11)	0.0145 (12)	0.0054 (12)
O1	0.0463 (14)	0.0305 (13)	0.0695 (18)	−0.0029 (10)	0.0246 (13)	0.0036 (12)
O2	0.0354 (13)	0.0334 (13)	0.0717 (18)	0.0040 (10)	0.0091 (12)	−0.0001 (13)
O3	0.0389 (14)	0.0581 (18)	0.081 (2)	0.0121 (12)	0.0263 (14)	0.0145 (15)
C1	0.0368 (16)	0.0330 (17)	0.0390 (17)	−0.0012 (13)	0.0150 (14)	−0.0018 (13)
C2	0.0339 (16)	0.0361 (17)	0.0394 (17)	−0.0012 (13)	0.0127 (13)	−0.0042 (14)
C3	0.0351 (17)	0.0407 (19)	0.055 (2)	−0.0013 (14)	0.0170 (15)	−0.0026 (16)
C4	0.040 (2)	0.103 (4)	0.073 (3)	−0.020 (2)	0.016 (2)	−0.031 (3)
C5	0.0339 (16)	0.0325 (16)	0.0357 (16)	0.0027 (13)	0.0078 (13)	−0.0011 (13)
C6	0.0377 (16)	0.0358 (17)	0.0291 (15)	−0.0024 (13)	0.0084 (13)	−0.0026 (13)
C7	0.0445 (19)	0.0371 (18)	0.0388 (18)	−0.0023 (14)	0.0144 (14)	0.0037 (15)
C8	0.050 (2)	0.046 (2)	0.048 (2)	−0.0106 (17)	0.0208 (17)	0.0061 (17)
C9	0.0376 (18)	0.059 (2)	0.047 (2)	−0.0065 (16)	0.0197 (15)	0.0021 (18)
C10	0.0362 (17)	0.048 (2)	0.0388 (17)	0.0028 (15)	0.0143 (14)	0.0013 (15)
C11	0.0349 (16)	0.0359 (17)	0.0330 (16)	−0.0012 (13)	0.0110 (13)	−0.0006 (13)
C12	0.039 (2)	0.083 (4)	0.108 (4)	0.017 (2)	0.025 (2)	0.000 (3)

N1—C1	1.364 (4)	C4—H4B	0.9600
N1—C11	1.367 (4)	C4—H4C	0.9600
N1—H1N	0.852 (19)	C5—C6	1.443 (4)
O1—C1	1.260 (4)	C6—C11	1.396 (5)
O2—C5	1.355 (4)	C6—C7	1.409 (5)
O2—H2	0.8200	C7—C8	1.369 (5)
O3—C10	1.365 (5)	C7—H7	0.9300
O3—C12	1.412 (5)	C8—C9	1.403 (6)
C1—C2	1.442 (5)	C8—H8	0.9300
C2—C5	1.359 (5)	C9—C10	1.363 (5)
C2—C3	1.503 (4)	C9—H9	0.9300
C3—C4	1.512 (6)	C10—C11	1.415 (5)
C3—H3A	0.9700	C12—H12A	0.9600
C3—H3B	0.9700	C12—H12B	0.9600
C4—H4A	0.9600	C12—H12C	0.9600
C1—N1—C11	123.9 (3)	C2—C5—C6	122.1 (3)
C1—N1—H1N	115 (3)	C11—C6—C7	119.3 (3)
C11—N1—H1N	121 (3)	C11—C6—C5	116.7 (3)
C5—O2—H2	109.5	C7—C6—C5	123.9 (3)
C10—O3—C12	118.4 (3)	C8—C7—C6	119.5 (3)
O1—C1—N1	119.1 (3)	C8—C7—H7	120.2
O1—C1—C2	123.4 (3)	C6—C7—H7	120.2
N1—C1—C2	117.4 (3)	C7—C8—C9	121.2 (3)
C5—C2—C1	119.3 (3)	C7—C8—H8	119.4
C5—C2—C3	123.0 (3)	C9—C8—H8	119.4
C1—C2—C3	117.7 (3)	C10—C9—C8	120.1 (3)
C2—C3—C4	112.3 (3)	C10—C9—H9	120.0
C2—C3—H3A	109.1	C8—C9—H9	120.0
C4—C3—H3A	109.1	C9—C10—O3	126.9 (3)
C2—C3—H3B	109.1	C9—C10—C11	119.7 (3)
C4—C3—H3B	109.1	O3—C10—C11	113.4 (3)
H3A—C3—H3B	107.9	N1—C11—C6	120.2 (3)
C3—C4—H4A	109.5	N1—C11—C10	119.6 (3)
C3—C4—H4B	109.5	C6—C11—C10	120.1 (3)
H4A—C4—H4B	109.5	O3—C12—H12A	109.5
C3—C4—H4C	109.5	O3—C12—H12B	109.5
H4A—C4—H4C	109.5	H12A—C12—H12B	109.5
H4B—C4—H4C	109.5	O3—C12—H12C	109.5
O2—C5—C2	117.8 (3)	H12A—C12—H12C	109.5
O2—C5—C6	120.0 (3)	H12B—C12—H12C	109.5
C11—N1—C1—O1	−178.8 (3)	C5—C6—C7—C8	179.6 (3)
C11—N1—C1—C2	3.3 (5)	C6—C7—C8—C9	−0.6 (5)
O1—C1—C2—C5	−176.7 (3)	C7—C8—C9—C10	−0.4 (6)
N1—C1—C2—C5	1.0 (5)	C8—C9—C10—O3	−177.8 (4)
O1—C1—C2—C3	1.6 (5)	C8—C9—C10—C11	1.4 (5)
N1—C1—C2—C3	179.4 (3)	C12—O3—C10—C9	−5.3 (6)
C5—C2—C3—C4	−89.5 (5)	C12—O3—C10—C11	175.5 (4)
C1—C2—C3—C4	92.3 (4)	C1—N1—C11—C6	−3.5 (5)
C1—C2—C5—O2	177.8 (3)	C1—N1—C11—C10	174.7 (3)
C3—C2—C5—O2	−0.5 (5)	C7—C6—C11—N1	178.6 (3)
C1—C2—C5—C6	−5.1 (5)	C5—C6—C11—N1	−0.5 (5)
C3—C2—C5—C6	176.7 (3)	C7—C6—C11—C10	0.3 (5)
O2—C5—C6—C11	−178.1 (3)	C5—C6—C11—C10	−178.8 (3)
C2—C5—C6—C11	4.8 (5)	C9—C10—C11—N1	−179.6 (3)
O2—C5—C6—C7	2.8 (5)	O3—C10—C11—N1	−0.3 (5)
C2—C5—C6—C7	−174.3 (3)	C9—C10—C11—C6	−1.3 (5)
C11—C6—C7—C8	0.6 (5)	O3—C10—C11—C6	178.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (2)	2.27 (3)	2.976 (4)	140 (3)
O2—H2···O1ii	0.82	1.94	2.665 (4)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (2)	2.27 (3)	2.976 (4)	140 (3)
O2—H2⋯O1ii	0.82	1.94	2.665 (4)	147

Symmetry codes: (i) ; (ii) .