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Acta Cryst. (2009). E65, o189    [ doi:10.1107/S1600536808042888 ]

(E)-4-Hydroxy-N'-(2-hydroxy-4-methoxybenzylidene)benzohydrazide monohydrate

N. Mohd Lair, H. Mohd Ali and S. W. Ng

Abstract top

The Schiff base molecule of the title compound, C15H14N2O4·H2O, adopts a trans configuration with respect to the C=N double bond; the Schiff base itself is almost planar (r.m.s. deviation for all non-H atoms = 0.040 Å). The amido N atom is the hydrogen-bond donor to the water molecule, which is the hydrogen-bond donor to the hydroxy groups of two neighboring molecules. One of the hydroxyl groups acts as an intramolecular and the other as an intermolecular hydrogen-bond donor.

Related literature top

For (E)-4-chloro-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide, which crystallizes as a monohydrate, see: Cui et al. (2007). For a set of similar compounds, see: Lu et al. (2008a,b,c). For compounds with antimalarial properties, see: Melnyk et al. (2006).

Experimental top

2-Hydroxy-3-methoxybenzaldehyde (0.30 g, 2 mmol) and 4-hydroxybenzohydrazide (0.30 g, 2 mmol) were heated in an ethanol-methanol mixture (50 ml) for 2 h. The solvent was removed and the resulting compound recrystallized from ethanol.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The oxygen- and nitrogen-bound ones were located in a difference Fourier map, and were refined with distance restraints (O–H 0.84±0.01, N–H 0.88±0.01 Å); their isotropic displacement parameters were freely refined.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C15H14N2O4.H2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
(E)-4-Hydroxy-N'-(2-hydroxy-4-methoxybenzylidene)benzohydrazide monohydrate top
Crystal data top
C15H14N2O4·H2OF(000) = 640
Mr = 304.30Dx = 1.402 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1918 reflections
a = 7.1763 (2) Åθ = 2.4–27.3°
b = 16.6507 (5) ŵ = 0.11 mm−1
c = 12.1828 (4) ÅT = 100 K
β = 98.022 (2)°Prism, yellow
V = 1441.48 (8) Å30.16 × 0.04 × 0.04 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		1903 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
graphiteθmax = 27.5°, θmin = 2.1°
ω scansh = −9→9
13327 measured reflectionsk = −21→21
3315 independent reflectionsl = −15→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0687P)2 + 1.4764P]
where P = (Fo2 + 2Fc2)/3
3315 reflections(Δ/σ)max = 0.001
200 parametersΔρmax = 0.66 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
C15H14N2O4·H2OV = 1441.48 (8) Å3
Mr = 304.30Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.1763 (2) ŵ = 0.11 mm−1
b = 16.6507 (5) ÅT = 100 K
c = 12.1828 (4) Å0.16 × 0.04 × 0.04 mm
β = 98.022 (2)°
Data collection top
Bruker SMART APEX
diffractometer		1903 reflections with I > 2σ(I)
13327 measured reflectionsRint = 0.053
3315 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.180Δρmax = 0.66 e Å−3
S = 1.05Δρmin = −0.43 e Å−3
3315 reflectionsAbsolute structure: ?
200 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7450 (3)0.31702 (12)1.09538 (15)0.0271 (5)
H10.77450.26981.11500.041*
O20.3884 (3)0.32742 (11)0.58919 (15)0.0246 (5)
O30.1758 (3)0.41831 (13)0.32215 (18)0.0444 (6)
H30.22620.40670.38660.067*
O4−0.1014 (3)0.59721 (14)0.05179 (16)0.0359 (6)
O50.4249 (4)0.61425 (14)0.73043 (18)0.0495 (7)
H510.40270.63630.78920.074*
H520.54200.61080.73170.074*
N10.3620 (3)0.45875 (14)0.62786 (18)0.0208 (5)
H110.38000.49870.67540.025*
N20.2800 (3)0.47111 (14)0.51985 (17)0.0218 (5)
C10.4997 (3)0.36829 (15)0.7739 (2)0.0174 (5)
C20.5351 (4)0.42869 (16)0.8536 (2)0.0204 (6)
H20.50120.48260.83450.024*
C30.6192 (4)0.41082 (16)0.9602 (2)0.0216 (6)
H3A0.64490.45241.01350.026*
C40.6653 (3)0.33229 (16)0.9886 (2)0.0197 (6)
C50.6322 (4)0.27144 (16)0.9108 (2)0.0214 (6)
H5A0.66550.21760.93050.026*
C60.5504 (4)0.28976 (16)0.8043 (2)0.0208 (6)
H60.52840.24810.75080.025*
C70.4134 (3)0.38292 (16)0.6579 (2)0.0191 (6)
C80.2221 (4)0.54217 (18)0.4913 (2)0.0231 (6)
H80.23620.58480.54360.028*
C90.1350 (4)0.55631 (18)0.3780 (2)0.0235 (6)
C100.1117 (4)0.49462 (18)0.2982 (2)0.0289 (7)
C110.0295 (4)0.5107 (2)0.1905 (2)0.0329 (7)
H11A0.01250.46890.13710.040*
C12−0.0278 (4)0.5882 (2)0.1614 (2)0.0281 (7)
C13−0.0097 (4)0.64983 (19)0.2380 (2)0.0290 (7)
H13−0.05190.70250.21770.035*
C140.0714 (4)0.63284 (18)0.3450 (2)0.0270 (6)
H140.08430.67490.39820.032*
C15−0.1581 (4)0.6759 (2)0.0151 (3)0.0385 (8)
H15A−0.20260.6749−0.06470.058*
H15B−0.05080.71270.02990.058*
H15C−0.25980.69440.05490.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0379 (11)0.0266 (11)0.0146 (9)0.0096 (9)−0.0039 (8)0.0015 (8)
O20.0309 (10)0.0230 (10)0.0188 (10)−0.0048 (8)−0.0008 (8)−0.0005 (8)
O30.0701 (17)0.0318 (13)0.0264 (12)−0.0012 (12)−0.0107 (11)0.0029 (10)
O40.0320 (12)0.0538 (15)0.0203 (10)0.0041 (10)−0.0018 (9)0.0118 (10)
O50.0772 (18)0.0431 (14)0.0259 (12)0.0265 (13)−0.0009 (12)−0.0119 (11)
N10.0228 (12)0.0233 (12)0.0152 (11)0.0005 (9)−0.0016 (9)0.0003 (9)
N20.0209 (11)0.0306 (13)0.0132 (11)−0.0014 (10)0.0004 (9)0.0039 (9)
C10.0136 (12)0.0223 (13)0.0164 (13)−0.0033 (10)0.0020 (10)−0.0001 (11)
C20.0201 (13)0.0213 (14)0.0197 (13)0.0023 (10)0.0027 (10)0.0031 (11)
C30.0260 (14)0.0207 (14)0.0172 (13)0.0012 (11)0.0001 (10)−0.0035 (11)
C40.0192 (13)0.0249 (14)0.0144 (12)0.0032 (11)0.0007 (10)0.0034 (11)
C50.0221 (13)0.0201 (14)0.0214 (13)0.0022 (11)0.0006 (11)0.0011 (11)
C60.0217 (13)0.0228 (14)0.0170 (13)−0.0005 (11)−0.0004 (11)−0.0033 (11)
C70.0173 (13)0.0225 (14)0.0176 (13)−0.0027 (10)0.0029 (10)0.0000 (11)
C80.0197 (13)0.0303 (15)0.0195 (14)0.0004 (11)0.0035 (11)0.0013 (12)
C90.0184 (13)0.0327 (16)0.0198 (14)−0.0033 (11)0.0043 (11)0.0066 (12)
C100.0333 (16)0.0286 (16)0.0242 (14)−0.0018 (13)0.0013 (12)0.0074 (13)
C110.0371 (17)0.0391 (18)0.0211 (15)−0.0053 (14)−0.0013 (12)0.0008 (13)
C120.0192 (14)0.0471 (19)0.0177 (14)−0.0008 (13)0.0011 (11)0.0108 (13)
C130.0237 (14)0.0358 (17)0.0269 (16)0.0055 (12)0.0018 (12)0.0123 (13)
C140.0235 (14)0.0327 (16)0.0249 (15)0.0039 (12)0.0043 (12)0.0033 (12)
C150.0314 (17)0.057 (2)0.0263 (16)0.0062 (16)0.0018 (13)0.0173 (16)
Geometric parameters (Å, °) top
O1—C41.370 (3)C3—H3A0.9500
O1—H10.8400C4—C51.385 (4)
O2—C71.243 (3)C5—C61.382 (4)
O3—C101.369 (4)C5—H5A0.9500
O3—H30.8400C6—H60.9500
O4—C121.374 (3)C8—C91.452 (4)
O4—C151.426 (4)C8—H80.9500
O5—H510.8400C9—C141.394 (4)
O5—H520.8400C9—C101.408 (4)
N1—C71.351 (3)C10—C111.387 (4)
N1—N21.380 (3)C11—C121.385 (4)
N1—H110.8800C11—H11A0.9500
N2—C81.286 (4)C12—C131.381 (4)
C1—C61.393 (4)C13—C141.381 (4)
C1—C21.396 (4)C13—H130.9500
C1—C71.482 (3)C14—H140.9500
C2—C31.386 (4)C15—H15A0.9800
C2—H20.9500C15—H15B0.9800
C3—C41.381 (4)C15—H15C0.9800
C4—O1—H1119.9N1—C7—C1118.3 (2)
C10—O3—H3120.0N2—C8—C9119.1 (3)
C12—O4—C15117.3 (3)N2—C8—H8120.5
H51—O5—H52108.8C9—C8—H8120.5
C7—N1—N2117.5 (2)C14—C9—C10117.7 (3)
C7—N1—H11121.3C14—C9—C8120.2 (3)
N2—N1—H11121.3C10—C9—C8122.1 (3)
C8—N2—N1118.3 (2)O3—C10—C11117.8 (3)
C6—C1—C2118.4 (2)O3—C10—C9121.7 (3)
C6—C1—C7117.8 (2)C11—C10—C9120.4 (3)
C2—C1—C7123.8 (2)C12—C11—C10119.6 (3)
C3—C2—C1120.7 (2)C12—C11—H11A120.2
C3—C2—H2119.7C10—C11—H11A120.2
C1—C2—H2119.7O4—C12—C13124.3 (3)
C4—C3—C2119.8 (2)O4—C12—C11114.2 (3)
C4—C3—H3A120.1C13—C12—C11121.5 (3)
C2—C3—H3A120.1C12—C13—C14118.3 (3)
O1—C4—C3117.9 (2)C12—C13—H13120.9
O1—C4—C5121.5 (2)C14—C13—H13120.9
C3—C4—C5120.5 (2)C13—C14—C9122.5 (3)
C6—C5—C4119.4 (2)C13—C14—H14118.7
C6—C5—H5A120.3C9—C14—H14118.7
C4—C5—H5A120.3O4—C15—H15A109.5
C5—C6—C1121.2 (2)O4—C15—H15B109.5
C5—C6—H6119.4H15A—C15—H15B109.5
C1—C6—H6119.4O4—C15—H15C109.5
O2—C7—N1120.3 (2)H15A—C15—H15C109.5
O2—C7—C1121.4 (2)H15B—C15—H15C109.5
C7—N1—N2—C8176.8 (2)N2—C8—C9—C14−179.9 (3)
C6—C1—C2—C30.2 (4)N2—C8—C9—C100.0 (4)
C7—C1—C2—C3−178.9 (2)C14—C9—C10—O3177.7 (3)
C1—C2—C3—C4−1.2 (4)C8—C9—C10—O3−2.2 (4)
C2—C3—C4—O1−178.8 (2)C14—C9—C10—C110.6 (4)
C2—C3—C4—C51.5 (4)C8—C9—C10—C11−179.3 (3)
O1—C4—C5—C6179.6 (2)O3—C10—C11—C12−176.4 (3)
C3—C4—C5—C6−0.7 (4)C9—C10—C11—C120.8 (4)
C4—C5—C6—C1−0.3 (4)C15—O4—C12—C131.6 (4)
C2—C1—C6—C50.6 (4)C15—O4—C12—C11−178.2 (3)
C7—C1—C6—C5179.7 (2)C10—C11—C12—O4178.0 (3)
N2—N1—C7—O20.7 (4)C10—C11—C12—C13−1.8 (4)
N2—N1—C7—C1−179.3 (2)O4—C12—C13—C14−178.4 (3)
C6—C1—C7—O2−0.7 (4)C11—C12—C13—C141.4 (4)
C2—C1—C7—O2178.4 (2)C12—C13—C14—C90.0 (4)
C6—C1—C7—N1179.3 (2)C10—C9—C14—C13−1.0 (4)
C2—C1—C7—N1−1.6 (4)C8—C9—C14—C13178.9 (3)
N1—N2—C8—C9−179.8 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.841.862.621 (3)150
O3—H3···N20.841.942.575 (3)132
O5—H51···O1ii0.842.032.833 (3)160
O5—H52···O3iii0.842.273.070 (4)160
N1—H11···O50.882.052.883 (3)158
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.841.862.621 (3)150
O3—H3···N20.841.942.575 (3)132
O5—H51···O1ii0.842.032.833 (3)160
O5—H52···O3iii0.842.273.070 (4)160
N1—H11···O50.882.052.883 (3)158
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1.
Acknowledgements top

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031, 12–02-03–2051).

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Cui, J., Yin, H. & Qiao, Y. (2007). Acta Cryst. E63, o3548.

Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008a). Acta Cryst. E64, o1693.

Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008b). Acta Cryst. E64, o1694.

Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008c). Acta Cryst. E64, o1695.

Melnyk, P., Leroux, V., Sergheraert, C. & Grellier, P. (2006). Bioorg. & Med. Chem. Lett. 16, 31–35.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.