7-Hy-droxy-1,2,3,4-tetra-hydro-quinolin-2-one dihydrate.

The asymmetric unit of the title compound, C(9)H(9)NO(2)·2H(2)O, comprises two independent organic mol-ecules and four water mol-ecules of crystallization. The heterocyclic rings are not planar: in one mol-ecule, the C atom bearing the O atom and the adjacent methyl-ene C atom are displaced by 0.320 (3) and 0.677 (3) Å, respectively, from the other eight atoms of the fused ring system. Equivalent values of 0.243 (3) and 0.659 (3) Å apply to the second mol-ecule. In the crystal, the components are linked by N-H⋯O and O-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For background to quinolin-2-ones as drugs, see: Braun et al. (2009a ▶,b ▶).

Experimental

Crystal data

C9H9NO2·2H2O

M = 199.20

Orthorhombic,

a = 15.4597 (16) Å

b = 12.7864 (12) Å

c = 20.312 (2) Å

V = 4015.1 (7) Å3

Z = 16

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.20 × 0.17 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.980, T max = 0.985

36302 measured reflections

3659 independent reflections

3061 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.175

S = 1.30

3659 reflections

287 parameters

14 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 datablock(s) global, I. DOI: 10.1107/S1600536812025263/hb6830sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025263/hb6830Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025263/hb6830Isup3.cml

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

C9H9NO2·2H2O	Dx = 1.318 Mg m−3
Mr = 199.20	Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, Pbca	Cell parameters from 11198 reflections
a = 15.4597 (16) Å	θ = 2.8–25.3°
b = 12.7864 (12) Å	µ = 0.10 mm−1
c = 20.312 (2) Å	T = 298 K
V = 4015.1 (7) Å3	Block, colorless
Z = 16	0.20 × 0.17 × 0.15 mm
F(000) = 1696

Bruker APEXII CCD diffractometer	3659 independent reflections
Radiation source: fine-focus sealed tube	3061 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
ω scan	θmax = 25.4°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −18→18
Tmin = 0.980, Tmax = 0.985	k = −15→15
36302 measured reflections	l = −24→22

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	w = 1/[σ2(Fo2) + (0.0561P)2 + 1.7267P] where P = (Fo2 + 2Fc2)/3
3659 reflections	(Δ/σ)max < 0.001
287 parameters	Δρmax = 0.15 e Å−3
14 restraints	Δρmin = −0.17 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
H6B	0.044 (4)	0.0608 (19)	0.2751 (18)	0.17 (2)*
H6A	0.049 (3)	0.012 (3)	0.2142 (6)	0.098 (14)*
O1	0.36079 (14)	0.44183 (15)	−0.04017 (9)	0.0563 (6)
O2	0.3059 (2)	0.18779 (19)	0.26380 (11)	0.0877 (9)
H2A	0.3128	0.2485	0.2756	0.132*
O3	0.06233 (14)	0.02384 (15)	0.12063 (10)	0.0586 (6)
O4	0.06082 (19)	0.31032 (17)	−0.17569 (10)	0.0706 (7)
H4	0.0693	0.2514	−0.1903	0.106*
O5	0.29566 (19)	0.49405 (18)	0.83784 (11)	0.0750 (7)
O6	0.0409 (2)	0.00260 (19)	0.25515 (12)	0.0779 (8)
O7	0.4001 (2)	0.6303 (2)	0.76488 (14)	0.0886 (9)
O8	0.8445 (2)	0.3721 (2)	0.18171 (13)	0.0800 (8)
N1	0.35559 (16)	0.35016 (17)	0.05386 (11)	0.0456 (6)
N2	0.07165 (16)	0.11997 (17)	0.02837 (11)	0.0465 (6)
C1	0.33970 (18)	0.3603 (2)	−0.01053 (13)	0.0430 (7)
C2	0.29447 (19)	0.2720 (2)	−0.04418 (14)	0.0488 (7)
H2C	0.3106	0.2716	−0.0903	0.059*
H2B	0.2325	0.2833	−0.0417	0.059*
C3	0.3158 (2)	0.1665 (2)	−0.01435 (15)	0.0550 (8)
H3A	0.2761	0.1144	−0.0314	0.066*
H3B	0.3739	0.1463	−0.0271	0.066*
C4	0.30961 (19)	0.1692 (2)	0.05908 (14)	0.0481 (7)
C5	0.2861 (2)	0.0849 (2)	0.09787 (16)	0.0611 (9)
H5	0.2708	0.0224	0.0776	0.073*
C6	0.2847 (2)	0.0905 (3)	0.16567 (16)	0.0666 (9)
H6	0.2689	0.0324	0.1905	0.080*
C7	0.3070 (2)	0.1830 (2)	0.19654 (15)	0.0600 (9)
C8	0.3304 (2)	0.2690 (2)	0.15928 (14)	0.0547 (8)
H8	0.3453	0.3315	0.1797	0.066*
C9	0.33155 (18)	0.2613 (2)	0.09142 (13)	0.0442 (7)
C10	0.05833 (18)	0.1108 (2)	0.09337 (14)	0.0470 (7)
C11	0.0364 (2)	0.2089 (2)	0.13002 (15)	0.0596 (8)
H11A	0.0521	0.2004	0.1759	0.071*
H11B	−0.0256	0.2204	0.1279	0.071*
C12	0.0823 (2)	0.3036 (2)	0.10257 (15)	0.0559 (8)
H12A	0.0577	0.3663	0.1218	0.067*
H12B	0.1429	0.3007	0.1147	0.067*
C13	0.07463 (18)	0.3091 (2)	0.02891 (14)	0.0453 (7)
C14	0.0744 (2)	0.4010 (2)	−0.00691 (15)	0.0542 (8)
H14	0.0774	0.4645	0.0154	0.065*
C15	0.0699 (2)	0.4015 (2)	−0.07439 (15)	0.0569 (8)
H15	0.0700	0.4647	−0.0971	0.068*
C16	0.06517 (19)	0.3081 (2)	−0.10861 (14)	0.0500 (7)
C17	0.06498 (18)	0.2143 (2)	−0.07431 (14)	0.0470 (7)
H17	0.0615	0.1511	−0.0968	0.056*
C18	0.06997 (18)	0.2159 (2)	−0.00617 (13)	0.0415 (6)
H1	0.379 (2)	0.4051 (18)	0.0750 (15)	0.080*
H2	0.085 (2)	0.0608 (16)	0.0065 (15)	0.080*
H8A	0.7976 (12)	0.407 (2)	0.1786 (18)	0.080*
H5B	0.317 (2)	0.476 (2)	0.8746 (9)	0.080*
H7A	0.4461 (13)	0.595 (2)	0.7583 (18)	0.080*
H8B	0.8793 (16)	0.412 (2)	0.2025 (16)	0.080*
H5A	0.292 (2)	0.4385 (16)	0.8149 (13)	0.080*
H7B	0.3651 (16)	0.591 (2)	0.7857 (17)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0830 (15)	0.0451 (12)	0.0409 (11)	−0.0094 (11)	−0.0055 (10)	0.0034 (9)
O2	0.156 (3)	0.0627 (15)	0.0439 (14)	−0.0189 (17)	−0.0015 (15)	0.0082 (11)
O3	0.0874 (16)	0.0441 (12)	0.0443 (12)	0.0079 (11)	0.0094 (10)	0.0045 (9)
O4	0.115 (2)	0.0526 (13)	0.0444 (13)	0.0070 (14)	−0.0001 (12)	0.0085 (10)
O5	0.119 (2)	0.0561 (14)	0.0498 (14)	0.0043 (14)	−0.0149 (14)	−0.0023 (11)
O6	0.130 (2)	0.0563 (14)	0.0474 (14)	0.0020 (15)	−0.0051 (15)	−0.0005 (12)
O7	0.124 (3)	0.0710 (18)	0.0709 (18)	0.0040 (16)	0.0160 (17)	0.0059 (14)
O8	0.108 (2)	0.0669 (16)	0.0649 (16)	0.0013 (15)	−0.0148 (15)	−0.0050 (13)
N1	0.0596 (16)	0.0379 (13)	0.0392 (13)	−0.0049 (11)	−0.0025 (11)	0.0006 (10)
N2	0.0634 (16)	0.0349 (13)	0.0413 (14)	0.0017 (11)	0.0053 (11)	−0.0006 (10)
C1	0.0461 (16)	0.0432 (16)	0.0395 (16)	0.0036 (13)	0.0015 (12)	−0.0038 (12)
C2	0.0556 (17)	0.0494 (17)	0.0413 (16)	−0.0053 (14)	−0.0023 (13)	−0.0060 (13)
C3	0.071 (2)	0.0421 (16)	0.0520 (19)	−0.0070 (15)	0.0026 (15)	−0.0079 (13)
C4	0.0549 (18)	0.0424 (16)	0.0470 (17)	−0.0011 (13)	−0.0012 (14)	−0.0023 (13)
C5	0.082 (2)	0.0413 (17)	0.060 (2)	−0.0107 (16)	−0.0020 (17)	−0.0019 (14)
C6	0.092 (3)	0.0486 (19)	0.059 (2)	−0.0148 (17)	−0.0024 (18)	0.0111 (15)
C7	0.085 (2)	0.0513 (19)	0.0436 (18)	−0.0088 (17)	−0.0035 (16)	0.0070 (14)
C8	0.074 (2)	0.0465 (17)	0.0437 (17)	−0.0039 (15)	−0.0055 (15)	−0.0001 (13)
C9	0.0499 (16)	0.0404 (15)	0.0423 (16)	−0.0009 (13)	−0.0009 (13)	0.0018 (12)
C10	0.0536 (18)	0.0463 (17)	0.0412 (16)	0.0042 (14)	0.0030 (13)	0.0000 (13)
C11	0.082 (2)	0.0498 (17)	0.0472 (18)	0.0075 (16)	0.0098 (16)	−0.0024 (14)
C12	0.074 (2)	0.0450 (17)	0.0490 (18)	0.0065 (15)	−0.0014 (16)	−0.0089 (13)
C13	0.0483 (16)	0.0404 (15)	0.0471 (16)	0.0055 (13)	0.0016 (13)	−0.0021 (12)
C14	0.069 (2)	0.0369 (16)	0.0571 (19)	0.0032 (14)	0.0042 (15)	−0.0038 (13)
C15	0.073 (2)	0.0368 (16)	0.060 (2)	0.0052 (15)	0.0011 (16)	0.0072 (14)
C16	0.0597 (19)	0.0469 (16)	0.0435 (16)	0.0026 (14)	0.0017 (14)	0.0049 (13)
C17	0.0560 (18)	0.0382 (15)	0.0469 (17)	−0.0011 (13)	0.0015 (13)	−0.0012 (12)
C18	0.0449 (16)	0.0377 (15)	0.0419 (16)	−0.0012 (12)	0.0018 (12)	0.0018 (12)

O1—C1	1.247 (3)	C3—H3B	0.9700
O2—C7	1.368 (4)	C4—C5	1.384 (4)
O2—H2A	0.8200	C4—C9	1.390 (4)
O3—C10	1.244 (3)	C5—C6	1.379 (4)
O4—C16	1.364 (3)	C5—H5	0.9300
O4—H4	0.8200	C6—C7	1.382 (4)
O5—H5B	0.851 (10)	C6—H6	0.9300
O5—H5A	0.851 (10)	C7—C8	1.383 (4)
O6—H6B	0.850 (10)	C8—C9	1.382 (4)
O6—H6A	0.850 (10)	C8—H8	0.9300
O7—H7A	0.854 (10)	C10—C11	1.498 (4)
O7—H7B	0.853 (10)	C11—C12	1.509 (4)
O8—H8A	0.853 (10)	C11—H11A	0.9700
O8—H8B	0.854 (10)	C11—H11B	0.9700
N1—C1	1.337 (3)	C12—C13	1.502 (4)
N1—C9	1.419 (3)	C12—H12A	0.9700
N1—H1	0.902 (10)	C12—H12B	0.9700
N2—C10	1.341 (3)	C13—C14	1.382 (4)
N2—C18	1.414 (3)	C13—C18	1.390 (4)
N2—H2	0.902 (10)	C14—C15	1.372 (4)
C1—C2	1.494 (4)	C14—H14	0.9300
C2—C3	1.516 (4)	C15—C16	1.384 (4)
C2—H2C	0.9700	C15—H15	0.9300
C2—H2B	0.9700	C16—C17	1.387 (4)
C3—C4	1.495 (4)	C17—C18	1.386 (4)
C3—H3A	0.9700	C17—H17	0.9300
C7—O2—H2A	109.5	C9—C8—C7	119.5 (3)
C16—O4—H4	109.5	C9—C8—H8	120.3
H5B—O5—H5A	106 (2)	C7—C8—H8	120.3
H6B—O6—H6A	109 (2)	C8—C9—C4	121.9 (3)
H7A—O7—H7B	107 (2)	C8—C9—N1	118.8 (2)
H8A—O8—H8B	105 (2)	C4—C9—N1	119.2 (2)
C1—N1—C9	123.8 (2)	O3—C10—N2	120.6 (2)
C1—N1—H1	118 (2)	O3—C10—C11	122.6 (3)
C9—N1—H1	118 (2)	N2—C10—C11	116.8 (2)
C10—N2—C18	124.2 (2)	C10—C11—C12	112.4 (2)
C10—N2—H2	117 (2)	C10—C11—H11A	109.1
C18—N2—H2	119 (2)	C12—C11—H11A	109.1
O1—C1—N1	120.4 (2)	C10—C11—H11B	109.1
O1—C1—C2	122.2 (2)	C12—C11—H11B	109.1
N1—C1—C2	117.4 (2)	H11A—C11—H11B	107.8
C1—C2—C3	112.9 (2)	C13—C12—C11	111.6 (3)
C1—C2—H2C	109.0	C13—C12—H12A	109.3
C3—C2—H2C	109.0	C11—C12—H12A	109.3
C1—C2—H2B	109.0	C13—C12—H12B	109.3
C3—C2—H2B	109.0	C11—C12—H12B	109.3
H2C—C2—H2B	107.8	H12A—C12—H12B	108.0
C4—C3—C2	111.4 (2)	C14—C13—C18	117.3 (3)
C4—C3—H3A	109.4	C14—C13—C12	124.4 (3)
C2—C3—H3A	109.4	C18—C13—C12	118.3 (2)
C4—C3—H3B	109.4	C15—C14—C13	122.0 (3)
C2—C3—H3B	109.4	C15—C14—H14	119.0
H3A—C3—H3B	108.0	C13—C14—H14	119.0
C5—C4—C9	117.0 (3)	C14—C15—C16	120.0 (3)
C5—C4—C3	124.5 (3)	C14—C15—H15	120.0
C9—C4—C3	118.4 (3)	C16—C15—H15	120.0
C6—C5—C4	122.2 (3)	O4—C16—C15	119.1 (3)
C6—C5—H5	118.9	O4—C16—C17	121.3 (3)
C4—C5—H5	118.9	C15—C16—C17	119.6 (3)
C5—C6—C7	119.6 (3)	C18—C17—C16	119.2 (3)
C5—C6—H6	120.2	C18—C17—H17	120.4
C7—C6—H6	120.2	C16—C17—H17	120.4
O2—C7—C6	119.2 (3)	C17—C18—C13	121.9 (2)
O2—C7—C8	120.9 (3)	C17—C18—N2	118.9 (2)
C6—C7—C8	119.8 (3)	C13—C18—N2	119.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O5	0.85 (1)	1.95 (1)	2.800 (4)	174 (3)
O5—H5A···O2i	0.85 (1)	1.93 (1)	2.774 (3)	170 (3)
O8—H8B···O6ii	0.85 (1)	1.90 (1)	2.751 (4)	177 (4)
O7—H7A···O6iii	0.85 (1)	1.94 (1)	2.791 (4)	172 (3)
O5—H5B···O1iv	0.85 (1)	1.91 (1)	2.757 (3)	176 (3)
O8—H8A···O5v	0.85 (1)	1.95 (1)	2.790 (4)	169 (4)
N2—H2···O1vi	0.90 (1)	1.98 (1)	2.867 (3)	169 (3)
N1—H1···O3vii	0.90 (1)	1.99 (1)	2.895 (3)	177 (3)
O4—H4···O7viii	0.82	1.86	2.668 (4)	170
O2—H2A···O8ix	0.82	1.87	2.671 (4)	166
O6—H6A···O3	0.85 (1)	1.92 (1)	2.766 (3)	175 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7B⋯O5	0.85 (1)	1.95 (1)	2.800 (4)	174 (3)
O5—H5A⋯O2i	0.85 (1)	1.93 (1)	2.774 (3)	170 (3)
O8—H8B⋯O6ii	0.85 (1)	1.90 (1)	2.751 (4)	177 (4)
O7—H7A⋯O6iii	0.85 (1)	1.94 (1)	2.791 (4)	172 (3)
O5—H5B⋯O1iv	0.85 (1)	1.91 (1)	2.757 (3)	176 (3)
O8—H8A⋯O5v	0.85 (1)	1.95 (1)	2.790 (4)	169 (4)
N2—H2⋯O1vi	0.90 (1)	1.98 (1)	2.867 (3)	169 (3)
N1—H1⋯O3vii	0.90 (1)	1.99 (1)	2.895 (3)	177 (3)
O4—H4⋯O7viii	0.82	1.86	2.668 (4)	170
O2—H2A⋯O8ix	0.82	1.87	2.671 (4)	166
O6—H6A⋯O3	0.85 (1)	1.92 (1)	2.766 (3)	175 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .