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Acta Cryst. (2008). E64, o1693    [ doi:10.1107/S1600536808024483 ]

N'-(2-Hydroxybenzylidene)-2-methoxybenzohydrazide monohydrate

J.-F. Lu, S.-T. Min, X.-H. Ji and Z.-H. Dang

Abstract top

In the title compound, C15H14N2O3·H2O, the Schiff base molecule is approximately planar, with a dihedral angle between the two aromatic rings of 10.2 (3)°. The molecular structure is stabilized by O-H...N and N-H...O hydrogen bonds. In the crystal structure, the Schiff base and water molecules are linked together by intermolecular O-H...O hydrogen bonds, forming chains parallel to the a axis.

Comment top

Schiff bases derived from the condensation of aldehydes with benzohydrazides have been widely investigated, either for their structures (Fun et al., 2008; Alhadi et al., 2008; Ali et al., 2007; Zou et al., 2004; Shan et al., 2008) or for their biological properties (Bedia et al., 2006; Terzioglu & Gürsoy, 2003). This study extends the structural study on such compounds. We report here the crystal structure of the title new Schiff base compound.

The asymmetric unit of the title compound consists of a Schiff base molecule and a water molecule of crystallization (Fig. 1). The bond lengths are within normal values (Allen et al., 1987), and are comparable to the values observed in similar compounds (Nie, 2008; He, 2008; Shi et al., 2007). The dihedral angle between the two aromatic rings in the Schiff base molecule is 10.2 (3)°, indicating that the molecule is approximately coplanar. The molecular structure is stabilized by O—H···N and N—H···O hydrogen bonds.

In the crystal structure (Fig. 2), the Schiff base and water molecules are linked into chains running parallel to the a axis by intermolecular O—H···O hydrogen bonds (Table 1).

Related literature top

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 top

The title compound was prepared by the Schiff base condensation of salicylaldehyde (0.1 mol) and 2-methoxybenzohydrazide (0.1 mmol) in ethanol (50 ml). The excess ethanol was removed by distillation. The colourless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were grown by slow evaporation from an ethanol solution at room temperature.

Refinement top

The imino and water H atoms were located in a difference map and refined with N–H, O–H, and H···H distances restrained to 0.90 (1), 0.85 (1), and 1.37 (2) Å, respectively. The other H atoms were positioned geometrically [C–H = 0.93-0.96 Å and O–H = 0.82 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C15 and O1). In the absence of significant anomalous scattering, Friedel pairs were merged.

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed approximately along the b axis.
N'-(2-Hydroxybenzylidene)-2-methoxybenzohydrazide monohydrate top
Crystal data top
C15H14N2O3·H2OF000 = 608
Mr = 288.30Dx = 1.360 Mg m−3
Orthorhombic, P212121Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1886 reflections
a = 4.761 (2) Åθ = 2.5–24.3º
b = 14.035 (3) ŵ = 0.10 mm−1
c = 21.073 (4) ÅT = 298 (2) K
V = 1408.1 (7) Å3Block, colourless
Z = 40.17 × 0.16 × 0.15 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		1808 independent reflections
Radiation source: fine-focus sealed tube1345 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
T = 298(2) Kθmax = 27.0º
ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −6→6
Tmin = 0.983, Tmax = 0.985k = −17→17
11662 measured reflectionsl = −26→26
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H 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 reflectionsΔρmax = 0.19 e Å−3
201 parametersΔρmin = −0.24 e Å−3
4 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C15H14N2O3·H2OV = 1408.1 (7) Å3
Mr = 288.30Z = 4
Orthorhombic, P212121Mo Kα
a = 4.761 (2) ŵ = 0.10 mm−1
b = 14.035 (3) ÅT = 298 (2) K
c = 21.073 (4) Å0.17 × 0.16 × 0.15 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		1808 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		1345 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 0.985Rint = 0.047
11662 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.130Δρmax = 0.19 e Å−3
S = 1.06Δρmin = −0.24 e Å−3
1808 reflectionsAbsolute structure: ?
201 parametersFlack parameter: ?
4 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
O11.0565 (6)0.25999 (15)0.11044 (10)0.0662 (7)
H10.94430.25160.13940.099*
O20.5284 (6)0.30810 (15)0.26095 (10)0.0632 (7)
O30.4681 (5)0.04698 (14)0.35246 (10)0.0600 (6)
O40.0300 (7)0.40911 (16)0.22254 (13)0.0761 (8)
N10.8661 (5)0.17231 (17)0.21429 (11)0.0447 (6)
N20.6938 (6)0.15858 (18)0.26624 (11)0.0475 (6)
C11.2024 (6)0.1040 (2)0.14441 (13)0.0430 (7)
C21.2117 (7)0.1808 (2)0.10233 (13)0.0454 (7)
C31.3847 (8)0.1756 (2)0.04953 (14)0.0596 (10)
H31.39080.22660.02140.072*
C41.5436 (8)0.0984 (2)0.03827 (15)0.0614 (9)
H41.65730.09680.00240.074*
C51.5411 (8)0.0215 (2)0.07896 (15)0.0617 (9)
H51.6533−0.03140.07110.074*
C61.3700 (8)0.0247 (2)0.13124 (15)0.0539 (8)
H61.3654−0.02720.15860.065*
C71.0217 (7)0.10236 (19)0.19971 (13)0.0450 (7)
H71.01970.04840.22530.054*
C80.5265 (7)0.2299 (2)0.28622 (13)0.0457 (7)
C90.3359 (7)0.2092 (2)0.34123 (13)0.0429 (7)
C100.3100 (7)0.1214 (2)0.37297 (13)0.0470 (7)
C110.1233 (7)0.1132 (3)0.42336 (14)0.0573 (9)
H110.10550.05530.44450.069*
C12−0.0358 (8)0.1904 (3)0.44229 (15)0.0637 (9)
H12−0.16160.18380.47580.076*
C13−0.0103 (8)0.2763 (2)0.41233 (14)0.0565 (8)
H13−0.11650.32830.42550.068*
C140.1751 (7)0.2848 (2)0.36233 (14)0.0509 (8)
H140.19250.34350.34220.061*
C150.4542 (10)−0.0415 (2)0.38602 (17)0.0750 (12)
H15A0.4918−0.03060.43020.112*
H15B0.5913−0.08470.36910.112*
H15C0.2700−0.06840.38130.112*
H20.695 (9)0.0996 (11)0.2825 (15)0.080*
H4A−0.113 (5)0.371 (2)0.2284 (19)0.080*
H4B0.169 (5)0.373 (2)0.2359 (18)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0823 (19)0.0551 (13)0.0613 (14)0.0192 (14)0.0190 (13)0.0106 (10)
O20.0598 (15)0.0610 (13)0.0688 (14)0.0056 (14)0.0168 (14)0.0188 (11)
O30.0623 (15)0.0557 (12)0.0621 (13)0.0040 (12)0.0182 (13)0.0086 (10)
O40.0771 (18)0.0626 (15)0.0885 (18)0.0020 (16)0.0056 (18)0.0012 (13)
N10.0417 (14)0.0533 (15)0.0390 (13)−0.0045 (13)0.0031 (12)−0.0012 (11)
N20.0474 (15)0.0540 (15)0.0412 (13)−0.0037 (14)0.0074 (13)0.0013 (11)
C10.0423 (17)0.0448 (15)0.0418 (15)−0.0052 (14)−0.0015 (14)−0.0042 (13)
C20.0482 (18)0.0461 (16)0.0417 (15)−0.0004 (16)0.0002 (14)−0.0049 (13)
C30.069 (2)0.059 (2)0.0506 (19)−0.002 (2)0.0155 (17)0.0066 (15)
C40.060 (2)0.075 (2)0.0495 (18)0.000 (2)0.0131 (17)−0.0117 (17)
C50.063 (2)0.0592 (19)0.063 (2)0.0121 (19)0.0074 (19)−0.0126 (17)
C60.065 (2)0.0448 (16)0.0517 (17)0.0021 (17)0.0014 (17)−0.0021 (14)
C70.0477 (18)0.0438 (15)0.0434 (15)−0.0057 (16)0.0056 (15)0.0007 (12)
C80.0374 (17)0.0563 (17)0.0433 (15)−0.0044 (17)0.0000 (15)−0.0030 (14)
C90.0359 (16)0.0546 (17)0.0381 (14)−0.0061 (14)−0.0052 (14)−0.0049 (13)
C100.0400 (17)0.0591 (18)0.0420 (15)−0.0043 (16)0.0003 (14)−0.0050 (14)
C110.053 (2)0.070 (2)0.0495 (18)−0.0070 (19)0.0073 (16)0.0069 (16)
C120.054 (2)0.087 (2)0.0494 (18)−0.005 (2)0.0116 (18)−0.0080 (17)
C130.048 (2)0.071 (2)0.0506 (17)0.0055 (19)0.0003 (18)−0.0131 (16)
C140.0474 (18)0.0572 (18)0.0482 (17)−0.0020 (17)−0.0032 (17)−0.0058 (15)
C150.085 (3)0.064 (2)0.075 (2)0.012 (2)0.012 (2)0.0219 (18)
Geometric parameters (Å, °) top
O1—C21.346 (4)C5—C61.371 (4)
O1—H10.8200C5—H50.93
O2—C81.220 (3)C6—H60.93
O3—C101.358 (4)C7—H70.93
O3—C151.430 (4)C8—C91.501 (4)
O4—H4A0.88 (3)C9—C141.383 (4)
O4—H4B0.88 (3)C9—C101.407 (4)
N1—C71.268 (3)C10—C111.389 (4)
N1—N21.381 (3)C11—C121.380 (5)
N2—C81.347 (4)C11—H110.93
N2—H20.897 (10)C12—C131.366 (5)
C1—C61.397 (4)C12—H120.93
C1—C21.397 (4)C13—C141.380 (4)
C1—C71.449 (4)C13—H130.93
C2—C31.386 (4)C14—H140.93
C3—C41.343 (5)C15—H15A0.96
C3—H30.93C15—H15B0.96
C4—C51.378 (4)C15—H15C0.96
C4—H40.93
C2—O1—H1109.5O2—C8—N2121.9 (3)
C10—O3—C15119.0 (3)O2—C8—C9121.1 (3)
H4A—O4—H4B101.2 (19)N2—C8—C9117.0 (3)
C7—N1—N2115.5 (2)C14—C9—C10118.1 (3)
C8—N2—N1119.7 (2)C14—C9—C8115.7 (3)
C8—N2—H2125 (3)C10—C9—C8126.2 (3)
N1—N2—H2115 (3)O3—C10—C11122.3 (3)
C6—C1—C2118.1 (3)O3—C10—C9118.2 (3)
C6—C1—C7119.1 (3)C11—C10—C9119.5 (3)
C2—C1—C7122.8 (3)C12—C11—C10120.5 (3)
O1—C2—C3118.1 (3)C12—C11—H11119.8
O1—C2—C1122.7 (3)C10—C11—H11119.8
C3—C2—C1119.2 (3)C13—C12—C11120.7 (3)
C4—C3—C2121.3 (3)C13—C12—H12119.7
C4—C3—H3119.4C11—C12—H12119.7
C2—C3—H3119.4C12—C13—C14119.1 (3)
C3—C4—C5121.1 (3)C12—C13—H13120.4
C3—C4—H4119.4C14—C13—H13120.4
C5—C4—H4119.4C13—C14—C9122.2 (3)
C6—C5—C4118.7 (3)C13—C14—H14118.9
C6—C5—H5120.7C9—C14—H14118.9
C4—C5—H5120.7O3—C15—H15A109.5
C5—C6—C1121.7 (3)O3—C15—H15B109.5
C5—C6—H6119.2H15A—C15—H15B109.5
C1—C6—H6119.2O3—C15—H15C109.5
N1—C7—C1122.0 (3)H15A—C15—H15C109.5
N1—C7—H7119.0H15B—C15—H15C109.5
C1—C7—H7119.0
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.972.669 (3)143
N2—H2···O30.90 (1)1.97 (3)2.629 (3)129 (3)
O4—H4B···O20.88 (3)2.01 (3)2.880 (4)171 (3)
O4—H4A···O2i0.88 (3)2.04 (2)2.893 (4)165 (4)
Symmetry codes: (i) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.972.669 (3)143
N2—H2···O30.90 (1)1.97 (3)2.629 (3)129 (3)
O4—H4B···O20.88 (3)2.01 (3)2.880 (4)171 (3)
O4—H4A···O2i0.88 (3)2.04 (2)2.893 (4)165 (4)
Symmetry codes: (i) x−1, y, z.
Acknowledgements top

The authors acknowledge Shaanxi University of Technology for the research fund.

references
References top

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