3-Hydr-oxy-7,8-dimethoxy-quinolin-2(1H)-one.

In the crystal structure of the title compound, C(11)H(11)NO(4), intra-molecular O-H⋯O hydrogen bonding results in the formation of a planar five-membered ring, which is nearly coplanar with the quinoline group. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For general background, see: Beak (1977 ▶); Nimlos et al. (1987 ▶); Rajnikant et al. (2002 ▶); Johnson (1996 ▶). For related literature, see: Lin et al. (2000 ▶); Song et al. (2006 ▶).

Experimental

Crystal data

C11H11NO4

M = 221.21

Monoclinic,

a = 4.9655 (16) Å

b = 14.084 (5) Å

c = 14.888 (5) Å

β = 96.208 (6)°

V = 1035.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 294 (2) K

0.60 × 0.37 × 0.31 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.937, T max = 0.967

6788 measured reflections

2228 independent reflections

1761 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.174

S = 1.08

2228 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 1999 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011549/hk2455sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011549/hk2455Isup2.hkl

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

C11H11NO4	F000 = 464
Mr = 221.21	Dx = 1.420 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 886 reflections
a = 4.9655 (16) Å	θ = 3.1–27.1º
b = 14.084 (5) Å	µ = 0.11 mm−1
c = 14.888 (5) Å	T = 294 (2) K
β = 96.208 (6)º	Block, colorless
V = 1035.1 (6) Å3	0.60 × 0.37 × 0.31 mm
Z = 4

Bruker CCD area-detector diffractometer	2228 independent reflections
Radiation source: fine-focus sealed tube	1761 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.015
T = 294(2) K	θmax = 27.1º
φ and ω scans	θmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −6→5
Tmin = 0.937, Tmax = 0.967	k = −17→15
6788 measured reflections	l = −18→18

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.174	w = 1/[σ2(Fo2) + (0.0907P)2 + 0.3738P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2228 reflections	Δρmax = 0.50 e Å−3
150 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2sigma(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
O1	−0.1615 (3)	0.39255 (11)	1.01266 (11)	0.0616 (5)
O2	−0.2273 (3)	0.20136 (9)	0.97741 (9)	0.0514 (4)
H2	−0.2816	0.2327	1.0182	0.077*
O3	0.6647 (4)	0.48962 (12)	0.67193 (12)	0.0681 (5)
O4	0.3678 (3)	0.54717 (9)	0.80367 (10)	0.0498 (4)
N1	0.1136 (3)	0.41905 (11)	0.90243 (11)	0.0439 (4)
H1	0.119 (5)	0.481 (2)	0.9155 (17)	0.068 (7)*
C1	−0.0380 (4)	0.36225 (14)	0.95063 (13)	0.0458 (5)
C2	−0.0452 (4)	0.26212 (14)	0.92587 (13)	0.0483 (5)
C3	0.0957 (4)	0.22783 (14)	0.86147 (14)	0.0500 (5)
H3A	0.0912	0.1632	0.8488	0.060*
C4	0.2532 (4)	0.28997 (13)	0.81204 (13)	0.0442 (4)
C5	0.2543 (4)	0.38754 (13)	0.83327 (12)	0.0404 (4)
C6	0.4035 (5)	0.26022 (15)	0.74343 (15)	0.0535 (5)
H6A	0.4079	0.1960	0.7290	0.064*
C7	0.5456 (5)	0.32376 (16)	0.69650 (15)	0.0544 (5)
H7A	0.6462	0.3021	0.6514	0.065*
C8	0.5392 (4)	0.42049 (15)	0.71632 (14)	0.0490 (5)
C9	0.3942 (4)	0.45222 (12)	0.78474 (13)	0.0427 (4)
C10	0.6032 (5)	0.58783 (16)	0.85291 (18)	0.0617 (6)
H10A	0.5711	0.6538	0.8638	0.093*
H10B	0.7547	0.5816	0.8184	0.093*
H10C	0.6416	0.5554	0.9095	0.093*
C11	0.8222 (6)	0.4614 (2)	0.60194 (19)	0.0789 (8)
H11A	0.8986	0.5166	0.5766	0.118*
H11B	0.7088	0.4286	0.5557	0.118*
H11C	0.9653	0.4200	0.6265	0.118*

	U11	U22	U33	U12	U13	U23
O1	0.0712 (10)	0.0546 (9)	0.0639 (9)	−0.0102 (7)	0.0302 (8)	−0.0133 (7)
O2	0.0809 (10)	0.0349 (7)	0.0397 (7)	−0.0015 (6)	0.0119 (6)	−0.0009 (5)
O3	0.0819 (12)	0.0579 (10)	0.0713 (10)	0.0009 (8)	0.0395 (9)	0.0048 (7)
O4	0.0549 (8)	0.0341 (7)	0.0615 (8)	0.0020 (6)	0.0117 (6)	−0.0013 (6)
N1	0.0498 (9)	0.0337 (8)	0.0496 (9)	−0.0009 (6)	0.0118 (7)	−0.0058 (6)
C1	0.0491 (10)	0.0431 (10)	0.0463 (10)	−0.0035 (8)	0.0096 (8)	−0.0056 (8)
C2	0.0559 (12)	0.0403 (10)	0.0488 (10)	−0.0069 (8)	0.0063 (9)	0.0001 (8)
C3	0.0620 (12)	0.0332 (9)	0.0552 (11)	−0.0018 (8)	0.0076 (9)	−0.0039 (8)
C4	0.0489 (10)	0.0360 (9)	0.0480 (10)	0.0022 (8)	0.0058 (8)	−0.0042 (7)
C5	0.0415 (9)	0.0371 (9)	0.0427 (9)	0.0037 (7)	0.0045 (7)	−0.0038 (7)
C6	0.0606 (13)	0.0398 (10)	0.0611 (12)	0.0061 (9)	0.0115 (10)	−0.0110 (9)
C7	0.0580 (12)	0.0521 (12)	0.0557 (11)	0.0083 (9)	0.0177 (9)	−0.0081 (9)
C8	0.0507 (11)	0.0471 (11)	0.0507 (11)	0.0033 (8)	0.0129 (9)	0.0029 (8)
C9	0.0452 (10)	0.0353 (9)	0.0480 (10)	0.0039 (7)	0.0061 (8)	−0.0005 (7)
C10	0.0622 (14)	0.0469 (11)	0.0779 (15)	−0.0108 (10)	0.0157 (11)	−0.0078 (10)
C11	0.0848 (18)	0.0863 (19)	0.0728 (16)	−0.0045 (15)	0.0419 (14)	0.0001 (14)

O2—H2	0.8200	C5—C4	1.410 (3)
O3—C11	1.425 (3)	C6—C7	1.376 (3)
O4—C9	1.376 (2)	C6—C4	1.393 (3)
O4—C10	1.430 (3)	C6—H6A	0.9300
N1—C1	1.356 (3)	C7—H7A	0.9300
N1—C5	1.379 (2)	C8—O3	1.365 (3)
N1—H1	0.90 (3)	C8—C9	1.384 (3)
C1—O1	1.238 (2)	C8—C7	1.395 (3)
C1—C2	1.457 (3)	C10—H10A	0.9600
C2—O2	1.513 (2)	C10—H10B	0.9600
C3—C2	1.337 (3)	C10—H10C	0.9600
C3—C4	1.430 (3)	C11—H11A	0.9600
C3—H3A	0.9300	C11—H11B	0.9600
C5—C9	1.394 (3)	C11—H11C	0.9600
C2—O2—H2	109.5	C4—C6—H6A	119.3
C8—O3—C11	118.1 (2)	C6—C7—C8	120.21 (19)
C9—O4—C10	113.78 (16)	C6—C7—H7A	119.9
C1—N1—C5	124.09 (16)	C8—C7—H7A	119.9
C1—N1—H1	117.9 (17)	O3—C8—C9	115.29 (18)
C5—N1—H1	118.0 (17)	O3—C8—C7	124.92 (19)
O1—C1—N1	122.64 (18)	C9—C8—C7	119.78 (19)
O1—C1—C2	121.43 (18)	O4—C9—C8	122.25 (17)
N1—C1—C2	115.93 (17)	O4—C9—C5	117.72 (17)
C3—C2—C1	122.03 (18)	C8—C9—C5	119.91 (17)
C3—C2—O2	123.18 (17)	O4—C10—H10A	109.5
C1—C2—O2	114.78 (17)	O4—C10—H10B	109.5
C2—C3—C4	120.40 (18)	H10A—C10—H10B	109.5
C2—C3—H3A	119.8	O4—C10—H10C	109.5
C4—C3—H3A	119.8	H10A—C10—H10C	109.5
C6—C4—C5	117.91 (18)	H10B—C10—H10C	109.5
C6—C4—C3	124.03 (18)	O3—C11—H11A	109.5
C5—C4—C3	118.06 (17)	O3—C11—H11B	109.5
N1—C5—C9	119.87 (16)	H11A—C11—H11B	109.5
N1—C5—C4	119.41 (17)	O3—C11—H11C	109.5
C9—C5—C4	120.72 (17)	H11A—C11—H11C	109.5
C7—C6—C4	121.43 (18)	H11B—C11—H11C	109.5
C7—C6—H6A	119.3
C10—O4—C9—C8	−77.3 (2)	C9—C5—C4—C3	−177.13 (18)
C10—O4—C9—C5	106.8 (2)	N1—C5—C9—O4	−5.1 (3)
C5—N1—C1—O1	179.73 (19)	C4—C5—C9—O4	174.46 (17)
C5—N1—C1—C2	0.4 (3)	N1—C5—C9—C8	178.93 (17)
C1—N1—C5—C9	176.93 (18)	C4—C5—C9—C8	−1.6 (3)
C1—N1—C5—C4	−2.6 (3)	C7—C6—C4—C5	−1.1 (3)
O1—C1—C2—C3	−177.3 (2)	C7—C6—C4—C3	178.2 (2)
N1—C1—C2—C3	2.0 (3)	C4—C6—C7—C8	−0.7 (3)
O1—C1—C2—O2	3.7 (3)	C9—C8—O3—C11	178.7 (2)
N1—C1—C2—O2	−176.97 (16)	C7—C8—O3—C11	−2.2 (4)
C4—C3—C2—C1	−2.1 (3)	O3—C8—C7—C6	−177.6 (2)
C4—C3—C2—O2	176.75 (17)	C9—C8—C7—C6	1.4 (3)
C2—C3—C4—C6	−179.4 (2)	O3—C8—C9—O4	3.0 (3)
C2—C3—C4—C5	−0.1 (3)	C7—C8—C9—O4	−176.09 (19)
N1—C5—C4—C6	−178.29 (18)	O3—C8—C9—C5	178.85 (17)
C9—C5—C4—C6	2.2 (3)	C7—C8—C9—C5	−0.3 (3)
N1—C5—C4—C3	2.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.90 (3)	2.07 (3)	2.938 (2)	161 (2)
O2—H2···O1	0.82	2.33	2.756 (2)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.90 (3)	2.07 (3)	2.938 (2)	161 (2)
O2—H2⋯O1	0.82	2.33	2.756 (2)	113

Symmetry code: (i) .