7-Hy­droxy-1,2,3,4-tetra­hydro­quinolin-2-one dihydrate

Zong, Q.-S.; Wu, J.-Y.

doi:10.1107/S1600536812025263

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2036

https://doi.org/10.1107/S1600536812025263

Open

access

7-Hydroxy-1,2,3,4-tetrahydroquinolin-2-one dihydrate

Qian-Shou Zong ^a ^* and Jian-Yi Wu ^a

^aCollege of Biology and Chemical Engineering, Jiaxing University, Jiaxing Zhejiang 314001, People's Republic of China
^*Correspondence e-mail: zongqianshou@163.com

(Received 30 May 2012; accepted 3 June 2012; online 13 June 2012)

The asymmetric unit of the title compound, C₉H₉NO₂·2H₂O, comprises two independent organic molecules and four water molecules of crystallization. The heterocyclic rings are not planar: in one molecule, the C atom bearing the O atom and the adjacent methylene 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 molecule. 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_r = 199.20
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.084
wR(F²) = 0.175
S = 1.30
3659 reflections
287 parameters
14 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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⋯O1^iv	0.85 (1)	1.91 (1)	2.757 (3)	176 (3)
O8—H8A⋯O5^v	0.85 (1)	1.95 (1)	2.790 (4)	169 (4)
N2—H2⋯O1^vi	0.90 (1)	1.98 (1)	2.867 (3)	169 (3)
N1—H1⋯O3^vii	0.90 (1)	1.99 (1)	2.895 (3)	177 (3)
O4—H4⋯O7^viii	0.82	1.86	2.668 (4)	170
O2—H2A⋯O8^ix	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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iv) x, y, z+1; (v) -x+1, -y+1, -z+1; (vi) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (vii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (viii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-1]$ ; (ix) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025263/hb6830sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025263/hb6830Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025263/hb6830Isup3.cml

checkCIF report

Comment top

7-Hydroxy-3,4-dihydro-1H-quinolin-2-one is an important intermediate for the preparation of non-typical antipsychotic drugs (Braun et al., 2009a,b). In this paper, the author reports the structure of the compound.

The asymmetric unit of the title compound comprises two independent 7-hydroxy-3,4-dihydro-1H-quinolin-2-one moleclues and four water molecules of crystallization (Fig. 1). In the crystal, 7-hydroxy-3,4-dihydro-1H-quinolin-2-one moleclues are linked by water molecules through hydrogen bonds (Table 1), to form a 3D network (Fig. 2).

Related literature top

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

Experimental top

7-Hydroxy-3,4-dihydro-1H-quinolin-2-one was obtained from Jiaxing Taixin Pharmaceutical Chemical Co., Ltd, and recrystallized from aqueous solution as colourless blocks.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecule of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal structure of the title compound, viewed along b axis. Hydrogen bonds are shown as dashed lines.

7-Hydroxy-1,2,3,4-tetrahydroquinolin-2-one dihydrate top

Crystal data top

C₉H₉NO₂·2H₂O	D_x = 1.318 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0561P)² + 1.7267P] where P = (F_o² + 2F_c²)/3
3659 reflections	(Δ/σ)_max < 0.001
287 parameters	Δρ_max = 0.15 e Å⁻³
14 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₉H₉NO₂·2H₂O	V = 4015.1 (7) Å³
M_r = 199.20	Z = 16
Orthorhombic, Pbca	Mo Kα radiation
a = 15.4597 (16) Å	µ = 0.10 mm⁻¹
b = 12.7864 (12) Å	T = 298 K
c = 20.312 (2) Å	0.20 × 0.17 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	3659 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3061 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.985	R_int = 0.058
36302 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	14 restraints
wR(F²) = 0.175	H atoms treated by a mixture of independent and constrained refinement
S = 1.30	Δρ_max = 0.15 e Å⁻³
3659 reflections	Δρ_min = −0.17 e Å⁻³
287 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.85 (1)	1.91 (1)	2.757 (3)	176 (3)
O8—H8A···O5^v	0.85 (1)	1.95 (1)	2.790 (4)	169 (4)
N2—H2···O1^vi	0.90 (1)	1.98 (1)	2.867 (3)	169 (3)
N1—H1···O3^vii	0.90 (1)	1.99 (1)	2.895 (3)	177 (3)
O4—H4···O7^viii	0.82	1.86	2.668 (4)	170
O2—H2A···O8^ix	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) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) x+1/2, −y+1/2, −z+1; (iv) x, y, z+1; (v) −x+1, −y+1, −z+1; (vi) −x+1/2, y−1/2, z; (vii) −x+1/2, y+1/2, z; (viii) −x+1/2, y−1/2, z−1; (ix) x−1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₉H₉NO₂·2H₂O
M_r	199.20
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	15.4597 (16), 12.7864 (12), 20.312 (2)
V (Å³)	4015.1 (7)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.17 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.980, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	36302, 3659, 3061
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.175, 1.30
No. of reflections	3659
No. of parameters	287
No. of restraints	14
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O5	0.853 (10)	1.950 (12)	2.800 (4)	174 (3)
O5—H5A···O2ⁱ	0.851 (10)	1.931 (12)	2.774 (3)	170 (3)
O8—H8B···O6ⁱⁱ	0.854 (10)	1.898 (11)	2.751 (4)	177 (4)
O7—H7A···O6ⁱⁱⁱ	0.854 (10)	1.943 (12)	2.791 (4)	172 (3)
O5—H5B···O1^iv	0.851 (10)	1.907 (10)	2.757 (3)	176 (3)
O8—H8A···O5^v	0.853 (10)	1.948 (13)	2.790 (4)	169 (4)
N2—H2···O1^vi	0.902 (10)	1.977 (13)	2.867 (3)	169 (3)
N1—H1···O3^vii	0.902 (10)	1.993 (11)	2.895 (3)	177 (3)
O4—H4···O7^viii	0.82	1.86	2.668 (4)	170
O2—H2A···O8^ix	0.82	1.87	2.671 (4)	166
O6—H6A···O3	0.850 (10)	1.918 (11)	2.766 (3)	175 (4)

Acknowledgements

We thank the Excellent Yong Teachers Program (No. 00511024) for financial support.

References

Braun, D. E., Gelbrich, T., Kahlenberg, V., Tessadri, R., Wieser, J. & Griesser, U. J. (2009a). Cryst. Growth Des., 9, 1054–1065. Web of Science CSD CrossRef CAS Google Scholar
Braun, D. E., Gelbrich, T., Kahlenberg, V., Tessadri, R., Wieser, J. & Griesser, U. J. (2009b). J. Pharm. Sci., 98, 2010–2026. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar