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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o189.
Published online 2008 December 20. doi:  10.1107/S1600536808042888
PMCID: PMC2968097

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

Abstract

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

For the structure of (E)-4-chloro-N′-(2-hydr­oxy-3-methoxy­benzyl­idene)benzo­hydrazide, which crystallizes as a monohydrate, see: Cui et al. (2007 [triangle]). For a series of similar compounds, see: Lu et al. (2008a [triangle],b [triangle],c [triangle]). For this and other compounds with anti­malarial properties, see: Melnyk et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o189-scheme1.jpg

Experimental

Crystal data

  • C15H14N2O4·H2O
  • M r = 304.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o189-efi1.jpg
  • a = 7.1763 (2) Å
  • b = 16.6507 (5) Å
  • c = 12.1828 (4) Å
  • β = 98.022 (2)°
  • V = 1441.48 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 100 (2) K
  • 0.16 × 0.04 × 0.04 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 13327 measured reflections
  • 3315 independent reflections
  • 1903 reflections with I > 2σ(I)
  • R int = 0.053

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.180
  • S = 1.05
  • 3315 reflections
  • 200 parameters
  • H-atom parameters constrained
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.43 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042888/bt2836sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042888/bt2836Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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.

Figures

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.

Crystal data

C15H14N2O4·H2OF(000) = 640
Mr = 304.30Dx = 1.402 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer1903 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

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 = 1.05w = 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 Å3
0 restraintsΔρmin = −0.43 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2836).

References

  • 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. [PMC free article] [PubMed]
  • Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008b). Acta Cryst. E64, o1694. [PMC free article] [PubMed]
  • Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008c). Acta Cryst. E64, o1695. [PMC free article] [PubMed]
  • Melnyk, P., Leroux, V., Sergheraert, C. & Grellier, P. (2006). Bioorg. & Med. Chem. Lett.16, 31–35. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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