N'-(4-Hydr-oxy-3-methoxy-benzyl-idene)acetohydrazide monohydrate.

In the title compound, C(10)H(12)N(2)O(3)·H(2)O, the Schiff base mol-ecule is approximately planar [within 0.189 (1) Å]. The inter-planar angle between the benzene and acetohydrazide planes is 8.50 (10)°. In the crystal, mol-ecules are linked into a three-dimensional network by strong and weak O-H⋯O and strong N-H⋯O hydrogen bonds. The hydr-oxy H atom deviates from the 4-hydr-oxy-3-methoxy-phenyl mean plane by 0.319 (2) Å, probably due to the involvement of this H atom in the O-H⋯O hydrogen bond. The weak O-H⋯O hydrogen bond is involved in a bifurcated hydrogen bond with R(1) (2)(4) motif. A weak C-H⋯π inter-action is also present.

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 ▶). For hydrogen bonds, see: Desiraju & Steiner (1999 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C10H12N2O3·H2O

M = 226.23

Orthorhombic,

a = 7.892 (2) Å

b = 16.374 (5) Å

c = 18.334 (6) Å

V = 2369.3 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 223 K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

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

11089 measured reflections

2138 independent reflections

1484 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.07

2138 reflections

159 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.19 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/S1600536809037489/fb2165sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037489/fb2165Isup2.hkl

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

C10H12N2O3·H2O	Dx = 1.268 Mg m−3
Mr = 226.23	Melting point = 492–494 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2085 reflections
a = 7.892 (2) Å	θ = 2.2–25.0°
b = 16.374 (5) Å	µ = 0.10 mm−1
c = 18.334 (6) Å	T = 223 K
V = 2369.3 (13) Å3	Block, colourless
Z = 8	0.24 × 0.20 × 0.18 mm
F(000) = 960

Bruker SMART CCD area-detector diffractometer	2138 independent reflections
Radiation source: fine-focus sealed tube	1484 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 25.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→8
Tmin = 0.977, Tmax = 0.979	k = −19→19
11089 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0602P)2 + 0.0171P] where P = (Fo2 + 2Fc2)/3
2138 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.18 e Å−3
41 constraints

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
O2	0.44998 (15)	0.16677 (8)	0.62044 (7)	0.0551 (4)
O1	0.58987 (17)	0.08238 (8)	0.51886 (7)	0.0548 (4)
H1	0.661 (3)	0.0446 (14)	0.4961 (12)	0.082*
N2	1.03345 (18)	0.42155 (9)	0.73839 (8)	0.0446 (4)
H2	1.131 (2)	0.4257 (11)	0.7207 (10)	0.053*
O3	0.85188 (16)	0.45567 (8)	0.82838 (7)	0.0593 (4)
N1	0.92032 (17)	0.36650 (8)	0.70786 (7)	0.0414 (4)
C7	0.8701 (2)	0.26735 (10)	0.61434 (9)	0.0400 (4)
C3	0.6871 (2)	0.14216 (10)	0.54766 (9)	0.0404 (4)
C4	0.7033 (2)	0.25087 (10)	0.63651 (9)	0.0415 (4)
H4	0.6540	0.2817	0.6735	0.050*
C2	0.6124 (2)	0.18899 (10)	0.60350 (9)	0.0399 (4)
C9	0.9926 (2)	0.46154 (11)	0.79905 (10)	0.0471 (5)
C8	0.9721 (2)	0.32982 (10)	0.65066 (9)	0.0427 (5)
H8	1.0776	0.3432	0.6315	0.051*
C5	0.8503 (2)	0.15935 (11)	0.52546 (9)	0.0453 (5)
H5	0.8992	0.1293	0.4879	0.054*
C6	0.9417 (2)	0.22132 (10)	0.55890 (9)	0.0452 (5)
H6	1.0521	0.2321	0.5440	0.054*
C10	1.1285 (3)	0.51521 (13)	0.83054 (11)	0.0679 (6)
H10A	1.2178	0.5219	0.7955	0.102*
H10B	1.1732	0.4904	0.8739	0.102*
H10C	1.0815	0.5676	0.8423	0.102*
C1	0.3699 (3)	0.20816 (14)	0.67877 (12)	0.0760 (7)
H1A	0.2576	0.1868	0.6854	0.114*
H1B	0.3636	0.2654	0.6679	0.114*
H1C	0.4342	0.2003	0.7227	0.114*
O1W	0.75904 (19)	−0.03511 (8)	0.45548 (8)	0.0579 (4)
H9A	0.791 (3)	−0.0175 (14)	0.4128 (12)	0.087*
H9B	0.676 (3)	−0.0698 (15)	0.4498 (13)	0.087*

	U11	U22	U33	U12	U13	U23
O2	0.0375 (8)	0.0614 (9)	0.0665 (9)	−0.0106 (6)	0.0067 (7)	−0.0210 (6)
O1	0.0473 (9)	0.0537 (8)	0.0635 (8)	−0.0095 (7)	0.0024 (7)	−0.0189 (6)
N2	0.0254 (8)	0.0517 (9)	0.0566 (10)	−0.0096 (7)	0.0013 (7)	−0.0094 (7)
O3	0.0361 (8)	0.0803 (10)	0.0615 (9)	−0.0070 (7)	0.0040 (7)	−0.0184 (7)
N1	0.0317 (9)	0.0435 (8)	0.0489 (9)	−0.0073 (6)	−0.0042 (7)	−0.0020 (7)
C7	0.0381 (11)	0.0419 (10)	0.0398 (9)	−0.0054 (8)	−0.0028 (8)	0.0050 (7)
C3	0.0413 (11)	0.0396 (9)	0.0402 (9)	−0.0029 (8)	−0.0045 (8)	0.0004 (8)
C4	0.0366 (11)	0.0447 (10)	0.0431 (9)	−0.0001 (8)	−0.0025 (8)	−0.0032 (7)
C2	0.0322 (10)	0.0421 (10)	0.0454 (10)	−0.0015 (8)	−0.0025 (8)	0.0005 (8)
C9	0.0324 (11)	0.0516 (11)	0.0571 (12)	−0.0013 (9)	−0.0033 (9)	−0.0094 (9)
C8	0.0339 (10)	0.0473 (10)	0.0469 (11)	−0.0060 (8)	0.0008 (8)	0.0020 (8)
C5	0.0478 (12)	0.0494 (11)	0.0387 (10)	−0.0036 (9)	0.0053 (8)	−0.0012 (8)
C6	0.0394 (11)	0.0502 (11)	0.0459 (10)	−0.0095 (8)	0.0068 (8)	0.0046 (8)
C10	0.0428 (13)	0.0720 (14)	0.0890 (16)	−0.0084 (11)	−0.0020 (11)	−0.0344 (12)
C1	0.0428 (13)	0.0937 (17)	0.0913 (16)	−0.0117 (12)	0.0174 (12)	−0.0392 (13)
O1W	0.0526 (10)	0.0591 (9)	0.0620 (8)	−0.0126 (7)	0.0080 (7)	−0.0117 (7)

O2—C2	1.368 (2)	C4—H4	0.9300
O2—C1	1.415 (2)	C9—C10	1.502 (3)
O1—C3	1.351 (2)	C8—H8	0.9300
O1—H1	0.93 (2)	C5—C6	1.388 (2)
N2—C9	1.330 (2)	C5—H5	0.9300
N2—N1	1.3868 (19)	C6—H6	0.9300
N2—H2	0.837 (15)	C10—H10A	0.9600
O3—C9	1.238 (2)	C10—H10B	0.9600
N1—C8	1.276 (2)	C10—H10C	0.9600
C7—C6	1.386 (2)	C1—H1A	0.9600
C7—C4	1.403 (2)	C1—H1B	0.9600
C7—C8	1.462 (2)	C1—H1C	0.9600
C3—C5	1.380 (3)	O1W—H9A	0.87 (2)
C3—C2	1.408 (2)	O1W—H9B	0.87 (3)
C4—C2	1.381 (2)
C2—O2—C1	117.56 (14)	N1—C8—H8	119.1
C3—O1—H1	108.4 (15)	C7—C8—H8	119.1
C9—N2—N1	120.09 (15)	C3—C5—C6	120.27 (16)
C9—N2—H2	120.5 (13)	C3—C5—H5	119.9
N1—N2—H2	119.1 (13)	C6—C5—H5	119.9
C8—N1—N2	115.58 (14)	C7—C6—C5	120.65 (16)
C6—C7—C4	119.35 (16)	C7—C6—H6	119.7
C6—C7—C8	119.34 (16)	C5—C6—H6	119.7
C4—C7—C8	121.25 (16)	C9—C10—H10A	109.5
O1—C3—C5	124.23 (16)	C9—C10—H10B	109.5
O1—C3—C2	116.17 (16)	H10A—C10—H10B	109.5
C5—C3—C2	119.60 (16)	C9—C10—H10C	109.5
C2—C4—C7	120.09 (16)	H10A—C10—H10C	109.5
C2—C4—H4	120.0	H10B—C10—H10C	109.5
C7—C4—H4	120.0	O2—C1—H1A	109.5
O2—C2—C4	125.62 (15)	O2—C1—H1B	109.5
O2—C2—C3	114.35 (14)	H1A—C1—H1B	109.5
C4—C2—C3	120.02 (16)	O2—C1—H1C	109.5
O3—C9—N2	122.85 (16)	H1A—C1—H1C	109.5
O3—C9—C10	121.28 (17)	H1B—C1—H1C	109.5
N2—C9—C10	115.87 (17)	H9A—O1W—H9B	109 (2)
N1—C8—C7	121.84 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1W	0.93 (2)	1.69 (2)	2.614 (2)	170 (2)
O1W—H9B···O1i	0.87 (3)	2.19 (3)	2.899 (2)	139 (2)
O1W—H9B···O2i	0.87 (3)	2.27 (2)	3.0506 (19)	148 (2)
N2—H2···O3ii	0.84 (2)	2.02 (2)	2.851 (2)	170 (2)
O1W—H9A···O3iii	0.87 (2)	1.91 (2)	2.768 (2)	167 (2)
C10—H10C···Cg1iv	0.96	2.91	3.581 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1W	0.93 (2)	1.69 (2)	2.614 (2)	170 (2)
O1W—H9B⋯O1i	0.87 (3)	2.19 (3)	2.899 (2)	139 (2)
O1W—H9B⋯O2i	0.87 (3)	2.27 (2)	3.0506 (19)	148 (2)
N2—H2⋯O3ii	0.837 (15)	2.023 (15)	2.851 (2)	169.6 (18)
O1W—H9A⋯O3iii	0.87 (2)	1.91 (2)	2.768 (2)	167 (2)
C10—H10C⋯Cg1iv	0.96	2.91	3.581 (3)	128

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C2–C7 ring.