3-Ethyl-3-hy-droxy-8-meth-oxy-quinoline-2,4(1H,3H)-dione monohydrate.

In the title hydrate, C(12)H(13)NO(4)·H(2)O, the piperidine ring that is fused to the benzene ring is in a sofa conformation with the chiral C atom lying 0.4084 (18) Å out of the plane of the nine fused-ring atoms. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the organic mol-ecules and water mol-ecules into chains running along the b-axis direction. The chains are further connected into layers parallel to the bc plane by π-π inter-actions between inversion-related benzene rings [centroid-centroid distance = 3.8846 (9) Å].

Related literature

For methods of preparation of 3-alkyl- or 3-aryl-3-hy­droxy­quinoline-2,4-diones by oxidation of the corresponding 3-alkyl- or 3-aryl­quinolin-2-ones, see: Stadlbauer & Kappe (1982 ▶); Stadlbauer et al. (1992 ▶). For naturally occurring 3-hy­droxy­quinoline-2,4-diones, see: Neuenhaus & Budzikiewicz (1979 ▶); Luo et al. (2009 ▶). For the biological activity of 3-hy­droxy­quinoline-2,4-diones, see: Prisyazhnyuk et al. (1984 ▶); Luo et al. (2009 ▶). For a related structure, see: Kafka et al. (2012 ▶).

Experimental

Crystal data

C12H13NO4·H2O

M = 253.25

Orthorhombic,

a = 16.5055 (4) Å

b = 8.8068 (2) Å

c = 16.6690 (4) Å

V = 2423.02 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.50 × 0.25 × 0.20 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.948, T max = 0.979

5200 measured reflections

2779 independent reflections

1963 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 1.03

2779 reflections

175 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.23 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: SIR92 (Altomare et al., 1994 ▶); 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/S1600536812043280/tk5162sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043280/tk5162Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043280/tk5162Isup3.cml

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

C12H13NO4·H2O	Dx = 1.388 Mg m−3
Mr = 253.25	Melting point = 371–372 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3161 reflections
a = 16.5055 (4) Å	θ = 1.0–27.5°
b = 8.8068 (2) Å	µ = 0.11 mm−1
c = 16.6690 (4) Å	T = 293 K
V = 2423.02 (10) Å3	Prism, yellow
Z = 8	0.50 × 0.25 × 0.20 mm
F(000) = 1072

Nonius KappaCCD area-detector diffractometer	2779 independent reflections
Radiation source: fine-focus sealed tube	1963 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ scans + ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	h = −21→21
Tmin = 0.948, Tmax = 0.979	k = −11→11
5200 measured reflections	l = −21→21

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0662P)2 + 0.4669P] where P = (Fo2 + 2Fc2)/3
2779 reflections	(Δ/σ)max = 0.0001
175 parameters	Δρmax = 0.26 e Å−3
3 restraints	Δρmin = −0.23 e Å−3

Experimental. 211 frames in 4 sets of φ scans + ω scans. Rotation/frame = 2 °. Crystal-detector distance = 31 mm. Measuring time = 20 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
O1	0.08014 (8)	0.56475 (12)	0.75104 (6)	0.0505 (3)
O2	0.04557 (8)	0.18242 (13)	0.56925 (8)	0.0576 (4)
O3	0.05871 (8)	0.26982 (13)	0.72594 (7)	0.0527 (3)
H3	0.0359	0.1965	0.7058	0.079*
O4	0.14902 (8)	0.81485 (13)	0.51080 (7)	0.0542 (3)
N1	0.11348 (8)	0.61105 (15)	0.62211 (7)	0.0395 (3)
H1N	0.1065 (10)	0.7068 (16)	0.6299 (11)	0.047*
C1	0.09586 (9)	0.51728 (17)	0.68405 (8)	0.0374 (3)
C2	0.10269 (9)	0.34757 (17)	0.66669 (9)	0.0392 (4)
C3	0.07607 (9)	0.30617 (16)	0.58203 (10)	0.0408 (4)
C4	0.09477 (9)	0.41692 (17)	0.51912 (9)	0.0381 (3)
C5	0.09051 (10)	0.3782 (2)	0.43780 (10)	0.0481 (4)
H5	0.0777	0.2795	0.4227	0.058*
C6	0.10534 (11)	0.4863 (2)	0.38047 (10)	0.0527 (4)
H6	0.1023	0.4608	0.3264	0.063*
C7	0.12485 (10)	0.6336 (2)	0.40285 (9)	0.0492 (4)
H7	0.1344	0.7062	0.3634	0.059*
C8	0.13022 (9)	0.67423 (18)	0.48253 (9)	0.0410 (4)
C9	0.11398 (9)	0.56549 (17)	0.54186 (8)	0.0358 (3)
C10	0.19372 (10)	0.3023 (2)	0.67026 (10)	0.0523 (4)
H10A	0.1986	0.1950	0.6581	0.063*
H10B	0.2228	0.3579	0.6291	0.063*
C11	0.23315 (12)	0.3326 (3)	0.74990 (11)	0.0683 (6)
H11A	0.2035	0.2817	0.7915	0.102*
H11B	0.2333	0.4399	0.7602	0.102*
H11C	0.2879	0.2957	0.7490	0.102*
C12	0.16490 (14)	0.9320 (2)	0.45424 (12)	0.0670 (6)
H12A	0.1179	0.9477	0.4214	0.101*
H12B	0.2099	0.9033	0.4210	0.101*
H12C	0.1777	1.0243	0.4822	0.101*
O1W	0.06321 (11)	0.90745 (16)	0.66799 (10)	0.0752 (5)
H1W	0.0478 (14)	0.978 (3)	0.6301 (13)	0.090*
H2W	0.0132 (11)	0.900 (3)	0.6914 (14)	0.090*

	U11	U22	U33	U12	U13	U23
O1	0.0709 (8)	0.0477 (7)	0.0329 (6)	0.0008 (5)	0.0073 (5)	−0.0009 (5)
O2	0.0692 (8)	0.0379 (6)	0.0657 (8)	−0.0052 (5)	−0.0121 (6)	−0.0034 (5)
O3	0.0674 (8)	0.0436 (6)	0.0472 (7)	−0.0100 (6)	0.0055 (6)	0.0084 (5)
O4	0.0786 (9)	0.0454 (6)	0.0386 (6)	−0.0116 (6)	0.0060 (6)	0.0066 (5)
N1	0.0543 (8)	0.0341 (6)	0.0301 (6)	−0.0024 (5)	0.0009 (5)	−0.0008 (5)
C1	0.0403 (8)	0.0402 (8)	0.0318 (7)	0.0000 (6)	0.0002 (6)	0.0013 (6)
C2	0.0440 (8)	0.0380 (8)	0.0357 (8)	0.0022 (6)	0.0002 (6)	0.0046 (6)
C3	0.0398 (8)	0.0368 (8)	0.0457 (9)	0.0065 (6)	−0.0034 (7)	−0.0034 (6)
C4	0.0369 (7)	0.0427 (8)	0.0346 (7)	0.0054 (6)	−0.0030 (6)	−0.0040 (6)
C5	0.0512 (9)	0.0533 (10)	0.0399 (9)	0.0082 (8)	−0.0058 (7)	−0.0118 (7)
C6	0.0588 (10)	0.0682 (11)	0.0312 (8)	0.0108 (9)	−0.0013 (7)	−0.0079 (8)
C7	0.0531 (9)	0.0626 (11)	0.0319 (8)	0.0079 (8)	0.0049 (7)	0.0053 (7)
C8	0.0429 (8)	0.0451 (9)	0.0349 (8)	0.0033 (6)	0.0040 (6)	0.0024 (7)
C9	0.0360 (7)	0.0418 (8)	0.0295 (7)	0.0037 (6)	−0.0001 (6)	0.0000 (6)
C10	0.0496 (9)	0.0584 (10)	0.0490 (10)	0.0130 (8)	−0.0069 (8)	0.0009 (8)
C11	0.0583 (11)	0.0913 (16)	0.0553 (11)	0.0106 (11)	−0.0155 (9)	−0.0012 (10)
C12	0.0872 (15)	0.0552 (11)	0.0587 (12)	−0.0077 (10)	0.0127 (10)	0.0164 (9)
O1W	0.0992 (11)	0.0548 (8)	0.0715 (10)	0.0047 (8)	0.0365 (9)	0.0061 (7)

O1—C1	1.2202 (17)	C6—C7	1.388 (3)
O2—C3	1.2193 (19)	C6—H6	0.9300
O3—C2	1.4040 (18)	C7—C8	1.378 (2)
O3—H3	0.8200	C7—H7	0.9300
O4—C8	1.361 (2)	C8—C9	1.402 (2)
O4—C12	1.422 (2)	C10—C11	1.502 (2)
N1—C1	1.3537 (19)	C10—H10A	0.9700
N1—C9	1.3966 (18)	C10—H10B	0.9700
N1—H1N	0.861 (14)	C11—H11A	0.9600
C1—C2	1.527 (2)	C11—H11B	0.9600
C2—C3	1.522 (2)	C11—H11C	0.9600
C2—C10	1.555 (2)	C12—H12A	0.9600
C3—C4	1.465 (2)	C12—H12B	0.9600
C4—C9	1.399 (2)	C12—H12C	0.9600
C4—C5	1.399 (2)	O1W—H1W	0.923 (16)
C5—C6	1.371 (3)	O1W—H2W	0.916 (16)
C5—H5	0.9300
C2—O3—H3	109.5	C8—C7—H7	119.5
C8—O4—C12	118.23 (14)	C6—C7—H7	119.5
C1—N1—C9	123.82 (13)	O4—C8—C7	125.75 (15)
C1—N1—H1N	117.0 (12)	O4—C8—C9	114.89 (13)
C9—N1—H1N	115.2 (12)	C7—C8—C9	119.34 (15)
O1—C1—N1	122.32 (14)	N1—C9—C4	121.80 (13)
O1—C1—C2	121.64 (13)	N1—C9—C8	118.71 (13)
N1—C1—C2	115.90 (12)	C4—C9—C8	119.41 (13)
O3—C2—C3	112.71 (13)	C11—C10—C2	114.01 (15)
O3—C2—C1	107.81 (12)	C11—C10—H10A	108.8
C3—C2—C1	112.89 (12)	C2—C10—H10A	108.8
O3—C2—C10	110.35 (13)	C11—C10—H10B	108.8
C3—C2—C10	104.65 (12)	C2—C10—H10B	108.8
C1—C2—C10	108.35 (13)	H10A—C10—H10B	107.6
O2—C3—C4	123.84 (15)	C10—C11—H11A	109.5
O2—C3—C2	119.69 (14)	C10—C11—H11B	109.5
C4—C3—C2	116.32 (13)	H11A—C11—H11B	109.5
C9—C4—C5	120.10 (14)	C10—C11—H11C	109.5
C9—C4—C3	118.46 (13)	H11A—C11—H11C	109.5
C5—C4—C3	121.38 (14)	H11B—C11—H11C	109.5
C6—C5—C4	119.83 (16)	O4—C12—H12A	109.5
C6—C5—H5	120.1	O4—C12—H12B	109.5
C4—C5—H5	120.1	H12A—C12—H12B	109.5
C5—C6—C7	120.20 (15)	O4—C12—H12C	109.5
C5—C6—H6	119.9	H12A—C12—H12C	109.5
C7—C6—H6	119.9	H12B—C12—H12C	109.5
C8—C7—C6	121.09 (16)	H1W—O1W—H2W	95 (2)
C9—N1—C1—O1	−165.15 (15)	C4—C5—C6—C7	0.2 (2)
C9—N1—C1—C2	19.1 (2)	C5—C6—C7—C8	0.4 (3)
O1—C1—C2—O3	22.8 (2)	C12—O4—C8—C7	−0.1 (3)
N1—C1—C2—O3	−161.35 (13)	C12—O4—C8—C9	−178.93 (16)
O1—C1—C2—C3	147.98 (15)	C6—C7—C8—O4	179.85 (16)
N1—C1—C2—C3	−36.19 (18)	C6—C7—C8—C9	−1.4 (2)
O1—C1—C2—C10	−96.60 (17)	C1—N1—C9—C4	0.9 (2)
N1—C1—C2—C10	79.22 (16)	C1—N1—C9—C8	177.65 (14)
O3—C2—C3—O2	−26.4 (2)	C5—C4—C9—N1	175.61 (14)
C1—C2—C3—O2	−148.87 (14)	C3—C4—C9—N1	−1.8 (2)
C10—C2—C3—O2	93.51 (17)	C5—C4—C9—C8	−1.1 (2)
O3—C2—C3—C4	157.87 (13)	C3—C4—C9—C8	−178.52 (14)
C1—C2—C3—C4	35.42 (18)	O4—C8—C9—N1	3.8 (2)
C10—C2—C3—C4	−82.20 (16)	C7—C8—C9—N1	−175.08 (14)
O2—C3—C4—C9	167.10 (15)	O4—C8—C9—C4	−179.40 (14)
C2—C3—C4—C9	−17.4 (2)	C7—C8—C9—C4	1.7 (2)
O2—C3—C4—C5	−10.3 (2)	O3—C2—C10—C11	−58.1 (2)
C2—C3—C4—C5	165.20 (14)	C3—C2—C10—C11	−179.62 (16)
C9—C4—C5—C6	0.1 (2)	C1—C2—C10—C11	59.70 (19)
C3—C4—C5—C6	177.47 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1i	0.82	2.35	2.9430 (17)	130
N1—H1N···O1W	0.86 (1)	2.01 (2)	2.8438 (19)	163 (2)
O1W—H1W···O2ii	0.92 (2)	2.07 (2)	2.9425 (19)	158 (2)
O1W—H2W···O3iii	0.92 (2)	2.15 (2)	2.9401 (19)	144 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1i	0.82	2.35	2.9430 (17)	130
N1—H1N⋯O1W	0.86 (1)	2.01 (2)	2.8438 (19)	163 (2)
O1W—H1W⋯O2ii	0.92 (2)	2.07 (2)	2.9425 (19)	158 (2)
O1W—H2W⋯O3iii	0.92 (2)	2.15 (2)	2.9401 (19)	144 (2)

Symmetry codes: (i) ; (ii) ; (iii) .