N'-(3,4-Dihydroxy-benzyl-idene)acetohydrazide monohydrate.

In the title compound, C(9)H(10)N(2)O(3)·H(2)O, the Schiff base mol-ecule is approximately planar, the dihedral angle between the benzene and acetohydrazide planes being 5.40 (7)°. An intra-molecular O-H⋯O hydrogen bond is observed. In the crystal, mol-ecules are linked into a two-dimensional network parallel to (100) by O-H⋯O, N-H⋯O, O-H⋯N and C-H⋯O hydrogen bonds, and by π-π inter-actions between symmetry-related benzene rings [centroid-centroid distance = 3.543 (2) Å].

Related literature

For general background to Schiff bases, see: Cimerman et al. (1997 ▶); Offe et al. (1952 ▶); Richardson et al. (1988 ▶). For related structures, see: Li & Jian (2008 ▶); Tamboura et al. (2009 ▶).

Experimental

Crystal data

C9H10N2O3·H2O

M = 212.21

Monoclinic,

a = 9.325 (4) Å

b = 13.877 (7) Å

c = 8.210 (4) Å

β = 106.435 (5)°

V = 1019.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 223 K

0.25 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.977, T max = 0.979

5060 measured reflections

1765 independent reflections

1640 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.102

S = 1.03

1765 reflections

148 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536809027299/ci2851sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027299/ci2851Isup2.hkl

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

C9H10N2O3·H2O	F(000) = 448
Mr = 212.21	Dx = 1.383 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1765 reflections
a = 9.325 (4) Å	θ = 2.3–25.0°
b = 13.877 (7) Å	µ = 0.11 mm−1
c = 8.210 (4) Å	T = 223 K
β = 106.435 (5)°	Block, colourless
V = 1019.0 (8) Å3	0.25 × 0.22 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1765 independent reflections
Radiation source: fine-focus sealed tube	1640 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −10→11
Tmin = 0.977, Tmax = 0.979	k = −16→15
5060 measured reflections	l = −9→9

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.061P)2 + 0.2305P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
1765 reflections	Δρmax = 0.17 e Å−3
148 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (5)

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
H1E	0.587 (2)	0.2853 (17)	0.445 (3)	0.074 (7)*
H1F	0.708 (3)	0.3160 (19)	0.554 (4)	0.098 (9)*
O1	0.52471 (13)	0.68267 (7)	0.22048 (14)	0.0454 (3)
H1	0.4899	0.6582	0.2919	0.068*
O2	0.56486 (12)	0.50802 (7)	0.36246 (13)	0.0457 (3)
H2	0.5820	0.4528	0.3981	0.068*
O3	0.95803 (14)	0.14282 (8)	0.12355 (14)	0.0552 (4)
C1	0.70188 (15)	0.45382 (10)	0.16721 (16)	0.0341 (3)
H1A	0.7158	0.3923	0.2140	0.041*
C6	0.75933 (14)	0.47698 (10)	0.03162 (16)	0.0338 (3)
C2	0.62483 (15)	0.52199 (9)	0.23148 (16)	0.0328 (3)
C3	0.60346 (15)	0.61461 (10)	0.16033 (17)	0.0345 (3)
C7	0.84173 (15)	0.40745 (10)	−0.04047 (17)	0.0366 (3)
H7	0.8769	0.4262	−0.1309	0.044*
C8	0.99310 (16)	0.17592 (10)	0.00126 (17)	0.0375 (3)
C4	0.66068 (17)	0.63811 (11)	0.02822 (19)	0.0418 (4)
H4	0.6473	0.6998	−0.0179	0.050*
C5	0.73807 (16)	0.56971 (11)	−0.03575 (18)	0.0412 (4)
H5	0.7765	0.5859	−0.1251	0.049*
N1	0.86712 (13)	0.32131 (8)	0.01702 (14)	0.0364 (3)
N2	0.94966 (13)	0.26400 (9)	−0.06162 (14)	0.0380 (3)
H2A	0.9728	0.2846	−0.1497	0.046*
C9	1.08651 (18)	0.12110 (13)	−0.08811 (19)	0.0483 (4)
H9A	1.1843	0.1107	−0.0117	0.072*
H9B	1.0949	0.1573	−0.1846	0.072*
H9C	1.0403	0.0601	−0.1254	0.072*
O1W	0.62190 (16)	0.32929 (8)	0.51868 (17)	0.0472 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0601 (7)	0.0354 (6)	0.0490 (6)	0.0077 (5)	0.0288 (5)	0.0011 (4)
O2	0.0665 (7)	0.0386 (6)	0.0438 (6)	0.0082 (5)	0.0350 (5)	0.0048 (4)
O3	0.0887 (9)	0.0445 (6)	0.0447 (6)	0.0080 (6)	0.0390 (6)	0.0052 (5)
C1	0.0409 (7)	0.0310 (7)	0.0331 (7)	0.0005 (5)	0.0148 (6)	0.0008 (5)
C6	0.0349 (7)	0.0369 (7)	0.0319 (7)	−0.0028 (5)	0.0133 (5)	−0.0022 (5)
C2	0.0366 (7)	0.0349 (7)	0.0295 (6)	−0.0026 (5)	0.0138 (5)	−0.0019 (5)
C3	0.0365 (7)	0.0322 (7)	0.0362 (7)	−0.0008 (5)	0.0127 (5)	−0.0031 (5)
C7	0.0399 (7)	0.0420 (8)	0.0324 (7)	−0.0034 (6)	0.0175 (6)	−0.0014 (6)
C8	0.0438 (8)	0.0430 (8)	0.0273 (6)	0.0011 (6)	0.0126 (6)	−0.0035 (5)
C4	0.0499 (8)	0.0342 (8)	0.0461 (8)	0.0014 (6)	0.0213 (7)	0.0073 (6)
C5	0.0457 (8)	0.0443 (8)	0.0401 (8)	−0.0023 (6)	0.0229 (6)	0.0055 (6)
N1	0.0408 (6)	0.0401 (7)	0.0336 (6)	0.0012 (5)	0.0191 (5)	−0.0028 (5)
N2	0.0478 (7)	0.0425 (7)	0.0317 (6)	0.0049 (5)	0.0242 (5)	0.0012 (5)
C9	0.0533 (9)	0.0556 (10)	0.0388 (8)	0.0155 (7)	0.0177 (7)	0.0000 (7)
O1W	0.0532 (7)	0.0412 (6)	0.0542 (7)	0.0047 (5)	0.0265 (6)	−0.0013 (5)

O1—C3	1.3713 (17)	C7—H7	0.93
O1—H1	0.82	C8—N2	1.3439 (19)
O2—C2	1.3591 (17)	C8—C9	1.496 (2)
O2—H2	0.82	C4—C5	1.383 (2)
O3—C8	1.2296 (18)	C4—H4	0.93
C1—C2	1.3799 (19)	C5—H5	0.93
C1—C6	1.4025 (19)	N1—N2	1.3868 (16)
C1—H1A	0.93	N2—H2A	0.86
C6—C5	1.392 (2)	C9—H9A	0.96
C6—C7	1.4592 (19)	C9—H9B	0.96
C2—C3	1.4025 (19)	C9—H9C	0.96
C3—C4	1.377 (2)	O1W—H1E	0.85 (3)
C7—N1	1.2823 (19)	O1W—H1F	0.80 (3)
C3—O1—H1	109.5	N2—C8—C9	115.35 (12)
C2—O2—H2	109.5	C3—C4—C5	119.80 (13)
C2—C1—C6	120.24 (12)	C3—C4—H4	120.1
C2—C1—H1A	119.9	C5—C4—H4	120.1
C6—C1—H1A	119.9	C4—C5—C6	120.95 (13)
C5—C6—C1	118.93 (13)	C4—C5—H5	119.5
C5—C6—C7	118.82 (12)	C6—C5—H5	119.5
C1—C6—C7	122.25 (12)	C7—N1—N2	115.60 (11)
O2—C2—C1	125.46 (12)	C8—N2—N1	119.30 (11)
O2—C2—C3	114.74 (12)	C8—N2—H2A	120.3
C1—C2—C3	119.80 (12)	N1—N2—H2A	120.3
O1—C3—C4	119.15 (12)	C8—C9—H9A	109.5
O1—C3—C2	120.57 (12)	C8—C9—H9B	109.5
C4—C3—C2	120.28 (13)	H9A—C9—H9B	109.5
N1—C7—C6	122.05 (12)	C8—C9—H9C	109.5
N1—C7—H7	119.0	H9A—C9—H9C	109.5
C6—C7—H7	119.0	H9B—C9—H9C	109.5
O3—C8—N2	122.18 (13)	H1E—O1W—H1F	103 (2)
O3—C8—C9	122.47 (14)
C2—C1—C6—C5	0.4 (2)	O1—C3—C4—C5	−178.86 (13)
C2—C1—C6—C7	179.90 (12)	C2—C3—C4—C5	0.7 (2)
C6—C1—C2—O2	−179.73 (12)	C3—C4—C5—C6	0.0 (2)
C6—C1—C2—C3	0.3 (2)	C1—C6—C5—C4	−0.5 (2)
O2—C2—C3—O1	−1.26 (18)	C7—C6—C5—C4	179.97 (13)
C1—C2—C3—O1	178.75 (12)	C6—C7—N1—N2	−178.62 (11)
O2—C2—C3—C4	179.15 (12)	O3—C8—N2—N1	2.4 (2)
C1—C2—C3—C4	−0.8 (2)	C9—C8—N2—N1	−177.75 (12)
C5—C6—C7—N1	179.01 (13)	C7—N1—N2—C8	173.80 (12)
C1—C6—C7—N1	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	2.22	2.6694 (18)	115
O1—H1···O1Wi	0.82	2.11	2.8529 (18)	151
O1W—H1F···O3ii	0.80 (3)	2.31 (3)	3.031 (2)	152 (3)
O1W—H1F···N1ii	0.80 (3)	2.48 (3)	3.101 (2)	135 (2)
O2—H2···O1W	0.82	1.96	2.7736 (18)	171
N2—H2A···O3iii	0.86	2.09	2.9110 (19)	160
C7—H7···O3iii	0.93	2.53	3.311 (2)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	2.22	2.6694 (18)	115
O1—H1⋯O1Wi	0.82	2.11	2.8529 (18)	151
O1W—H1F⋯O3ii	0.80 (3)	2.31 (3)	3.031 (2)	152 (3)
O1W—H1F⋯N1ii	0.80 (3)	2.48 (3)	3.101 (2)	135 (2)
O2—H2⋯O1W	0.82	1.96	2.7736 (18)	171
N2—H2A⋯O3iii	0.86	2.09	2.9110 (19)	160
C7—H7⋯O3iii	0.93	2.53	3.311 (2)	142

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