N'-(2-Hydroxy-benzyl-idene)-2-methoxy-benzohydrazide monohydrate.

In the title compound, C(15)H(14)N(2)O(3)·H(2)O, the Schiff base mol-ecule is approximately planar, with a dihedral angle between the two aromatic rings of 10.2 (3)°. The mol-ecular structure is stabilized by O-H⋯N and N-H⋯O hydrogen bonds. In the crystal structure, the Schiff base and water mol-ecules are linked together by inter-molecular O-H⋯O hydrogen bonds, forming chains parallel to the a axis.

Related literature

For general background on Schiff bases derived from condensation of aldehydes with benzohydrazides, see: Fun et al. (2008 ▶); Alhadi et al. (2008 ▶); Ali et al. (2007 ▶); Zou et al. (2004 ▶); Shan et al. (2008 ▶); Bedia et al. (2006 ▶); Terzioglu & Gürsoy (2003 ▶). For related structures, see: Nie (2008 ▶); He (2008 ▶); Shi et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14N2O3·H2O

M = 288.30

Orthorhombic,

a = 4.761 (2) Å

b = 14.035 (3) Å

c = 21.073 (4) Å

V = 1408.1 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 (2) K

0.17 × 0.16 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.983, T max = 0.985

11662 measured reflections

1808 independent reflections

1345 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.130

S = 1.06

1808 reflections

201 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.24 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 datablocks global, I. DOI: 10.1107/S1600536808024483/ci2646sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024483/ci2646Isup2.hkl

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

C15H14N2O3·H2O	F000 = 608
Mr = 288.30	Dx = 1.360 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1886 reflections
a = 4.761 (2) Å	θ = 2.5–24.3º
b = 14.035 (3) Å	µ = 0.10 mm−1
c = 21.073 (4) Å	T = 298 (2) K
V = 1408.1 (7) Å3	Block, colourless
Z = 4	0.17 × 0.16 × 0.15 mm

Bruker APEXII CCD area-detector diffractometer	1808 independent reflections
Radiation source: fine-focus sealed tube	1345 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −6→6
Tmin = 0.983, Tmax = 0.985	k = −17→17
11662 measured reflections	l = −26→26

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0693P)2 + 0.0505P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
1808 reflections	Δρmax = 0.19 e Å−3
201 parameters	Δρmin = −0.24 e Å−3
4 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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
O1	1.0565 (6)	0.25999 (15)	0.11044 (10)	0.0662 (7)
H1	0.9443	0.2516	0.1394	0.099*
O2	0.5284 (6)	0.30810 (15)	0.26095 (10)	0.0632 (7)
O3	0.4681 (5)	0.04698 (14)	0.35246 (10)	0.0600 (6)
O4	0.0300 (7)	0.40911 (16)	0.22254 (13)	0.0761 (8)
N1	0.8661 (5)	0.17231 (17)	0.21429 (11)	0.0447 (6)
N2	0.6938 (6)	0.15858 (18)	0.26624 (11)	0.0475 (6)
C1	1.2024 (6)	0.1040 (2)	0.14441 (13)	0.0430 (7)
C2	1.2117 (7)	0.1808 (2)	0.10233 (13)	0.0454 (7)
C3	1.3847 (8)	0.1756 (2)	0.04953 (14)	0.0596 (10)
H3	1.3908	0.2266	0.0214	0.072*
C4	1.5436 (8)	0.0984 (2)	0.03827 (15)	0.0614 (9)
H4	1.6573	0.0968	0.0024	0.074*
C5	1.5411 (8)	0.0215 (2)	0.07896 (15)	0.0617 (9)
H5	1.6533	−0.0314	0.0711	0.074*
C6	1.3700 (8)	0.0247 (2)	0.13124 (15)	0.0539 (8)
H6	1.3654	−0.0272	0.1586	0.065*
C7	1.0217 (7)	0.10236 (19)	0.19971 (13)	0.0450 (7)
H7	1.0197	0.0484	0.2253	0.054*
C8	0.5265 (7)	0.2299 (2)	0.28622 (13)	0.0457 (7)
C9	0.3359 (7)	0.2092 (2)	0.34123 (13)	0.0429 (7)
C10	0.3100 (7)	0.1214 (2)	0.37297 (13)	0.0470 (7)
C11	0.1233 (7)	0.1132 (3)	0.42336 (14)	0.0573 (9)
H11	0.1055	0.0553	0.4445	0.069*
C12	−0.0358 (8)	0.1904 (3)	0.44229 (15)	0.0637 (9)
H12	−0.1616	0.1838	0.4758	0.076*
C13	−0.0103 (8)	0.2763 (2)	0.41233 (14)	0.0565 (8)
H13	−0.1165	0.3283	0.4255	0.068*
C14	0.1751 (7)	0.2848 (2)	0.36233 (14)	0.0509 (8)
H14	0.1925	0.3435	0.3422	0.061*
C15	0.4542 (10)	−0.0415 (2)	0.38602 (17)	0.0750 (12)
H15A	0.4918	−0.0306	0.4302	0.112*
H15B	0.5913	−0.0847	0.3691	0.112*
H15C	0.2700	−0.0684	0.3813	0.112*
H2	0.695 (9)	0.0996 (11)	0.2825 (15)	0.080*
H4A	−0.113 (5)	0.371 (2)	0.2284 (19)	0.080*
H4B	0.169 (5)	0.373 (2)	0.2359 (18)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0823 (19)	0.0551 (13)	0.0613 (14)	0.0192 (14)	0.0190 (13)	0.0106 (10)
O2	0.0598 (15)	0.0610 (13)	0.0688 (14)	0.0056 (14)	0.0168 (14)	0.0188 (11)
O3	0.0623 (15)	0.0557 (12)	0.0621 (13)	0.0040 (12)	0.0182 (13)	0.0086 (10)
O4	0.0771 (18)	0.0626 (15)	0.0885 (18)	0.0020 (16)	0.0056 (18)	0.0012 (13)
N1	0.0417 (14)	0.0533 (15)	0.0390 (13)	−0.0045 (13)	0.0031 (12)	−0.0012 (11)
N2	0.0474 (15)	0.0540 (15)	0.0412 (13)	−0.0037 (14)	0.0074 (13)	0.0013 (11)
C1	0.0423 (17)	0.0448 (15)	0.0418 (15)	−0.0052 (14)	−0.0015 (14)	−0.0042 (13)
C2	0.0482 (18)	0.0461 (16)	0.0417 (15)	−0.0004 (16)	0.0002 (14)	−0.0049 (13)
C3	0.069 (2)	0.059 (2)	0.0506 (19)	−0.002 (2)	0.0155 (17)	0.0066 (15)
C4	0.060 (2)	0.075 (2)	0.0495 (18)	0.000 (2)	0.0131 (17)	−0.0117 (17)
C5	0.063 (2)	0.0592 (19)	0.063 (2)	0.0121 (19)	0.0074 (19)	−0.0126 (17)
C6	0.065 (2)	0.0448 (16)	0.0517 (17)	0.0021 (17)	0.0014 (17)	−0.0021 (14)
C7	0.0477 (18)	0.0438 (15)	0.0434 (15)	−0.0057 (16)	0.0056 (15)	0.0007 (12)
C8	0.0374 (17)	0.0563 (17)	0.0433 (15)	−0.0044 (17)	0.0000 (15)	−0.0030 (14)
C9	0.0359 (16)	0.0546 (17)	0.0381 (14)	−0.0061 (14)	−0.0052 (14)	−0.0049 (13)
C10	0.0400 (17)	0.0591 (18)	0.0420 (15)	−0.0043 (16)	0.0003 (14)	−0.0050 (14)
C11	0.053 (2)	0.070 (2)	0.0495 (18)	−0.0070 (19)	0.0073 (16)	0.0069 (16)
C12	0.054 (2)	0.087 (2)	0.0494 (18)	−0.005 (2)	0.0116 (18)	−0.0080 (17)
C13	0.048 (2)	0.071 (2)	0.0506 (17)	0.0055 (19)	0.0003 (18)	−0.0131 (16)
C14	0.0474 (18)	0.0572 (18)	0.0482 (17)	−0.0020 (17)	−0.0032 (17)	−0.0058 (15)
C15	0.085 (3)	0.064 (2)	0.075 (2)	0.012 (2)	0.012 (2)	0.0219 (18)

O1—C2	1.346 (4)	C5—C6	1.371 (4)
O1—H1	0.8200	C5—H5	0.93
O2—C8	1.220 (3)	C6—H6	0.93
O3—C10	1.358 (4)	C7—H7	0.93
O3—C15	1.430 (4)	C8—C9	1.501 (4)
O4—H4A	0.88 (3)	C9—C14	1.383 (4)
O4—H4B	0.88 (3)	C9—C10	1.407 (4)
N1—C7	1.268 (3)	C10—C11	1.389 (4)
N1—N2	1.381 (3)	C11—C12	1.380 (5)
N2—C8	1.347 (4)	C11—H11	0.93
N2—H2	0.897 (10)	C12—C13	1.366 (5)
C1—C6	1.397 (4)	C12—H12	0.93
C1—C2	1.397 (4)	C13—C14	1.380 (4)
C1—C7	1.449 (4)	C13—H13	0.93
C2—C3	1.386 (4)	C14—H14	0.93
C3—C4	1.343 (5)	C15—H15A	0.96
C3—H3	0.93	C15—H15B	0.96
C4—C5	1.378 (4)	C15—H15C	0.96
C4—H4	0.93
C2—O1—H1	109.5	O2—C8—N2	121.9 (3)
C10—O3—C15	119.0 (3)	O2—C8—C9	121.1 (3)
H4A—O4—H4B	101.2 (19)	N2—C8—C9	117.0 (3)
C7—N1—N2	115.5 (2)	C14—C9—C10	118.1 (3)
C8—N2—N1	119.7 (2)	C14—C9—C8	115.7 (3)
C8—N2—H2	125 (3)	C10—C9—C8	126.2 (3)
N1—N2—H2	115 (3)	O3—C10—C11	122.3 (3)
C6—C1—C2	118.1 (3)	O3—C10—C9	118.2 (3)
C6—C1—C7	119.1 (3)	C11—C10—C9	119.5 (3)
C2—C1—C7	122.8 (3)	C12—C11—C10	120.5 (3)
O1—C2—C3	118.1 (3)	C12—C11—H11	119.8
O1—C2—C1	122.7 (3)	C10—C11—H11	119.8
C3—C2—C1	119.2 (3)	C13—C12—C11	120.7 (3)
C4—C3—C2	121.3 (3)	C13—C12—H12	119.7
C4—C3—H3	119.4	C11—C12—H12	119.7
C2—C3—H3	119.4	C12—C13—C14	119.1 (3)
C3—C4—C5	121.1 (3)	C12—C13—H13	120.4
C3—C4—H4	119.4	C14—C13—H13	120.4
C5—C4—H4	119.4	C13—C14—C9	122.2 (3)
C6—C5—C4	118.7 (3)	C13—C14—H14	118.9
C6—C5—H5	120.7	C9—C14—H14	118.9
C4—C5—H5	120.7	O3—C15—H15A	109.5
C5—C6—C1	121.7 (3)	O3—C15—H15B	109.5
C5—C6—H6	119.2	H15A—C15—H15B	109.5
C1—C6—H6	119.2	O3—C15—H15C	109.5
N1—C7—C1	122.0 (3)	H15A—C15—H15C	109.5
N1—C7—H7	119.0	H15B—C15—H15C	109.5
C1—C7—H7	119.0

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.97	2.669 (3)	143
N2—H2···O3	0.90 (1)	1.97 (3)	2.629 (3)	129 (3)
O4—H4B···O2	0.88 (3)	2.01 (3)	2.880 (4)	171 (3)
O4—H4A···O2i	0.88 (3)	2.04 (2)	2.893 (4)	165 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.97	2.669 (3)	143
N2—H2⋯O3	0.90 (1)	1.97 (3)	2.629 (3)	129 (3)
O4—H4B⋯O2	0.88 (3)	2.01 (3)	2.880 (4)	171 (3)
O4—H4A⋯O2i	0.88 (3)	2.04 (2)	2.893 (4)	165 (4)

Symmetry code: (i) .