Methyl 2-(4-hy-droxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)acetate.

In the title compound, C(13)H(13)NO(4), the bicyclic quinolone fragment and the ester group are approximately orthogonal, making a dihedral angle of 83.3 (2)° and an intramolecular C-H⋯O interaction occurs. In the crystal, inter-molecular O-H⋯O hydrogen bonding generates a zigzag chain along the c axis.

Related literature

Esters of 4-hy­droxy-2-oxo-1,2-dihydro­quinolin-3-acetic acids reveal appreciable biological activity, see: Ukrainets et al. (2010 ▶). For a related structure, see: Ukrainets et al. (2009 ▶). For van der Waals radii, see: Zefirov (1997 ▶). For reference bond lengths, see: Bürgi & Dunitz (1994 ▶).

Experimental

Crystal data

C13H13NO4

M = 247.24

Monoclinic,

a = 9.0792 (6) Å

b = 11.4904 (6) Å

c = 11.4071 (7) Å

β = 105.272 (7)°

V = 1148.00 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Oxford Xcalibur3 diffractometer

11774 measured reflections

3295 independent reflections

1454 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.082

S = 0.72

3295 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis RED; data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP (Siemens, 1998 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810046453/kp2282sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046453/kp2282Isup2.hkl

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

C13H13NO4	F(000) = 520
Mr = 247.24	Dx = 1.431 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.0792 (6) Å	Cell parameters from 3049 reflections
b = 11.4904 (6) Å	θ = 2.9–32.1°
c = 11.4071 (7) Å	µ = 0.11 mm−1
β = 105.272 (7)°	T = 293 K
V = 1148.00 (12) Å3	Block, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Oxford Xcalibur3 diffractometer	1454 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	Rint = 0.031
graphite	θmax = 30.0°, θmin = 2.9°
Detector resolution: 16.1827 pixels mm-1	h = −12→12
ω scans	k = −15→16
11774 measured reflections	l = −16→16
3295 independent reflections

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)] = 0.035	Hydrogen site location: difference Fourier map
wR(F2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 0.72	w = 1/[σ2(Fo2) + (0.044P)2] where P = (Fo2 + 2Fc2)/3
3295 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.27207 (11)	0.49052 (8)	0.49471 (8)	0.0442 (3)
O1	0.39749 (11)	0.33292 (7)	0.44953 (8)	0.0582 (3)
O2	0.26304 (11)	0.34913 (8)	0.82386 (8)	0.0565 (3)
H2O	0.3143 (18)	0.2811 (15)	0.8511 (15)	0.100 (6)*
O3	0.19057 (12)	0.11214 (7)	0.58965 (9)	0.0613 (3)
O4	0.41580 (10)	0.02233 (7)	0.61834 (8)	0.0576 (3)
C1	0.19562 (14)	0.54717 (10)	0.56935 (11)	0.0412 (3)
C2	0.11931 (15)	0.65295 (10)	0.53520 (13)	0.0538 (4)
H2	0.1204	0.6877	0.4618	0.065*
C3	0.04276 (16)	0.70527 (12)	0.61044 (14)	0.0615 (4)
H3	−0.0073	0.7755	0.5873	0.074*
C4	0.03911 (16)	0.65520 (11)	0.71953 (14)	0.0591 (4)
H4	−0.0132	0.6916	0.7693	0.071*
C5	0.11239 (14)	0.55205 (11)	0.75432 (12)	0.0500 (3)
H5	0.1093	0.5183	0.8277	0.060*
C6	0.19244 (13)	0.49640 (9)	0.68027 (10)	0.0404 (3)
C7	0.27042 (13)	0.38819 (10)	0.71437 (10)	0.0411 (3)
C8	0.34114 (14)	0.33278 (9)	0.63922 (11)	0.0416 (3)
C9	0.33855 (14)	0.38309 (10)	0.52337 (11)	0.0433 (3)
C10	0.42339 (14)	0.21863 (10)	0.66808 (12)	0.0487 (3)
H10B	0.5113	0.2192	0.6348	0.058*
H10A	0.4607	0.2112	0.7556	0.058*
C11	0.32703 (16)	0.11471 (10)	0.61955 (11)	0.0439 (3)
C12	0.33896 (18)	−0.08538 (12)	0.57708 (14)	0.0681 (4)
H12C	0.2641	−0.1004	0.6209	0.102*
H12B	0.4120	−0.1477	0.5910	0.102*
H12A	0.2895	−0.0800	0.4918	0.102*
C13	0.27996 (17)	0.54417 (12)	0.38000 (11)	0.0600 (4)
H13C	0.3199	0.6217	0.3953	0.090*
H13B	0.1795	0.5472	0.3254	0.090*
H13A	0.3456	0.4988	0.3442	0.090*

	U11	U22	U33	U12	U13	U23
N1	0.0566 (7)	0.0417 (6)	0.0338 (6)	−0.0103 (5)	0.0112 (5)	−0.0002 (4)
O1	0.0705 (6)	0.0588 (6)	0.0493 (6)	−0.0083 (5)	0.0230 (5)	−0.0177 (4)
O2	0.0725 (7)	0.0558 (6)	0.0474 (6)	0.0058 (5)	0.0269 (5)	0.0123 (5)
O3	0.0581 (6)	0.0474 (6)	0.0775 (7)	−0.0025 (5)	0.0159 (5)	−0.0014 (4)
O4	0.0650 (6)	0.0387 (5)	0.0674 (6)	0.0057 (4)	0.0144 (5)	−0.0046 (4)
C1	0.0428 (7)	0.0371 (7)	0.0410 (7)	−0.0088 (5)	0.0064 (5)	−0.0028 (5)
C2	0.0580 (9)	0.0469 (8)	0.0511 (9)	−0.0068 (7)	0.0049 (7)	0.0062 (6)
C3	0.0560 (9)	0.0444 (8)	0.0781 (11)	0.0047 (7)	0.0071 (8)	−0.0007 (7)
C4	0.0554 (9)	0.0539 (9)	0.0672 (10)	0.0045 (7)	0.0150 (7)	−0.0136 (7)
C5	0.0506 (8)	0.0524 (8)	0.0467 (8)	−0.0019 (6)	0.0125 (6)	−0.0069 (6)
C6	0.0444 (7)	0.0354 (6)	0.0403 (7)	−0.0057 (5)	0.0090 (5)	−0.0048 (5)
C7	0.0478 (7)	0.0382 (7)	0.0375 (7)	−0.0080 (6)	0.0117 (6)	−0.0002 (5)
C8	0.0464 (7)	0.0355 (6)	0.0435 (7)	−0.0070 (5)	0.0127 (6)	−0.0027 (5)
C9	0.0468 (7)	0.0417 (7)	0.0423 (8)	−0.0117 (6)	0.0131 (6)	−0.0099 (5)
C10	0.0529 (8)	0.0414 (7)	0.0537 (8)	0.0001 (6)	0.0174 (6)	−0.0016 (6)
C11	0.0577 (9)	0.0385 (7)	0.0377 (7)	0.0003 (7)	0.0164 (6)	0.0019 (5)
C12	0.0916 (11)	0.0384 (8)	0.0681 (10)	0.0022 (7)	0.0100 (8)	−0.0086 (6)
C13	0.0731 (10)	0.0644 (9)	0.0426 (8)	−0.0146 (7)	0.0152 (7)	0.0062 (6)

N1—C9	1.3751 (15)	C4—H4	0.9300
N1—C1	1.3936 (15)	C5—C6	1.4049 (16)
N1—C13	1.4652 (15)	C5—H5	0.9300
O1—C9	1.2512 (14)	C6—C7	1.4330 (16)
O2—C7	1.3454 (14)	C7—C8	1.3574 (16)
O2—H2O	0.921 (17)	C8—C9	1.4370 (17)
O3—C11	1.1957 (14)	C8—C10	1.5023 (15)
O4—C11	1.3351 (14)	C10—C11	1.4975 (17)
O4—C12	1.4378 (15)	C10—H10B	0.9700
C1—C6	1.4005 (16)	C10—H10A	0.9700
C1—C2	1.4025 (17)	C12—H12C	0.9600
C2—C3	1.3766 (19)	C12—H12B	0.9600
C2—H2	0.9300	C12—H12A	0.9600
C3—C4	1.379 (2)	C13—H13C	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.3660 (17)	C13—H13A	0.9600
C9—N1—C1	122.15 (10)	C7—C8—C10	124.17 (11)
C9—N1—C13	117.93 (11)	C9—C8—C10	116.07 (11)
C1—N1—C13	119.90 (11)	O1—C9—N1	119.49 (11)
C7—O2—H2O	116.9 (10)	O1—C9—C8	121.83 (12)
C11—O4—C12	116.46 (10)	N1—C9—C8	118.66 (11)
N1—C1—C6	119.31 (11)	C11—C10—C8	114.01 (10)
N1—C1—C2	121.62 (11)	C11—C10—H10B	108.8
C6—C1—C2	119.06 (12)	C8—C10—H10B	108.8
C3—C2—C1	119.92 (13)	C11—C10—H10A	108.8
C3—C2—H2	120.0	C8—C10—H10A	108.8
C1—C2—H2	120.0	H10B—C10—H10A	107.6
C2—C3—C4	121.09 (13)	O3—C11—O4	124.09 (11)
C2—C3—H3	119.5	O3—C11—C10	125.86 (11)
C4—C3—H3	119.5	O4—C11—C10	110.01 (11)
C5—C4—C3	119.90 (13)	O4—C12—H12C	109.5
C5—C4—H4	120.1	O4—C12—H12B	109.5
C3—C4—H4	120.1	H12C—C12—H12B	109.5
C4—C5—C6	120.65 (13)	O4—C12—H12A	109.5
C4—C5—H5	119.7	H12C—C12—H12A	109.5
C6—C5—H5	119.7	H12B—C12—H12A	109.5
C1—C6—C5	119.38 (11)	N1—C13—H13C	109.5
C1—C6—C7	118.71 (11)	N1—C13—H13B	109.5
C5—C6—C7	121.91 (11)	H13C—C13—H13B	109.5
O2—C7—C8	125.26 (11)	N1—C13—H13A	109.5
O2—C7—C6	113.55 (10)	H13C—C13—H13A	109.5
C8—C7—C6	121.18 (11)	H13B—C13—H13A	109.5
C7—C8—C9	119.75 (11)
C9—N1—C1—C6	3.30 (16)	O2—C7—C8—C9	178.97 (10)
C13—N1—C1—C6	−178.30 (10)	C6—C7—C8—C9	0.14 (17)
C9—N1—C1—C2	−175.55 (11)	O2—C7—C8—C10	−0.41 (19)
C13—N1—C1—C2	2.85 (17)	C6—C7—C8—C10	−179.24 (10)
N1—C1—C2—C3	178.85 (11)	C1—N1—C9—O1	175.57 (11)
C6—C1—C2—C3	−0.01 (17)	C13—N1—C9—O1	−2.86 (16)
C1—C2—C3—C4	−0.2 (2)	C1—N1—C9—C8	−5.80 (16)
C2—C3—C4—C5	0.0 (2)	C13—N1—C9—C8	175.77 (11)
C3—C4—C5—C6	0.3 (2)	C7—C8—C9—O1	−177.38 (11)
N1—C1—C6—C5	−178.52 (11)	C10—C8—C9—O1	2.05 (17)
C2—C1—C6—C5	0.36 (16)	C7—C8—C9—N1	4.03 (17)
N1—C1—C6—C7	0.99 (15)	C10—C8—C9—N1	−176.54 (10)
C2—C1—C6—C7	179.87 (11)	C7—C8—C10—C11	93.90 (14)
C4—C5—C6—C1	−0.53 (18)	C9—C8—C10—C11	−85.50 (13)
C4—C5—C6—C7	179.98 (11)	C12—O4—C11—O3	0.54 (18)
C1—C6—C7—O2	178.39 (10)	C12—O4—C11—C10	178.27 (11)
C5—C6—C7—O2	−2.12 (16)	C8—C10—C11—O3	−19.67 (18)
C1—C6—C7—C8	−2.65 (16)	C8—C10—C11—O4	162.65 (10)
C5—C6—C7—C8	176.84 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1i	0.921 (17)	1.760 (17)	2.6456 (12)	160.2 (15)
C10—H10A···O1i	0.97	2.48	3.3335 (16)	147
C5—H5···O2	0.93	2.40	2.7138 (16)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1i	0.921 (17)	1.760 (17)	2.6456 (12)	160.2 (15)
C10—H10A⋯O1i	0.97	2.48	3.3335 (16)	147

Symmetry code: (i) .