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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2316.
Published online 2009 September 5. doi:  10.1107/S1600536809033236
PMCID: PMC2970457

N′-(3-Eth­oxy-2-hydroxy­benzyl­idene)-4-hydr­oxy-3-methoxy­benzohydrazide monohydrate

Abstract

In the title compound, C17H18N2O5·H2O, the dihedral angle between the two aromatic rings is 7.86 (7)° and an intra­molecular O—H(...)N hydrogen bond is observed. In the crystal structure, mol­ecules are linked into a three-dimensional network by inter­molecular O—H(...)O and N—H(...)O hydrogen bonds.

Related literature

For related structures, see: Lu et al. (2008a [triangle],b [triangle],c [triangle]); Abdul Alhadi et al. (2009 [triangle]); Mohd Lair et al. (2009 [triangle]); Narayana et al. (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2316-scheme1.jpg

Experimental

Crystal data

  • C17H18N2O5·H2O
  • M r = 348.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2316-efi1.jpg
  • a = 9.4063 (11) Å
  • b = 10.0598 (12) Å
  • c = 17.667 (2) Å
  • β = 93.702 (2)°
  • V = 1668.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 K
  • 0.23 × 0.20 × 0.20 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.976, T max = 0.979
  • 9554 measured reflections
  • 3606 independent reflections
  • 2530 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.111
  • S = 1.05
  • 3606 reflections
  • 239 parameters
  • 4 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033236/ci2887sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033236/ci2887Isup2.hkl

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

Acknowledgments

The author thanks the Scientific Research Foundation of Shaanxi University of Technology for financial support (project No. SLGQD0708).

supplementary crystallographic information

Comment

Schiff bases and their metal complexes have received much attention in recent years. As part of our investigation on crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b,c), we report herein the crystal structure of the title new Schiff base compound.

The asymmetric unit of the title compound (Fig. 1), consists of a Schiff base molecule and a water molecule of crystallization. The bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Abdul Alhadi et al., 2009; Mohd Lair et al., 2009; Narayana et al., 2007). The dihedral angle between the two aromatic rings is 7.86 (7)°, indicating that they are approximately coplanar. The methoxy and ethoxy groups are coplanar with the attached rings [C17—O4—C11—C10 = 4.6 (2)°, C15—O2—C3—C4 = -2.6 (2)° and C3—O2—C15—C16 = 177.98 (14)]. An intramolecular O—H···N hydrogen bond is observed (Table 1 and Fig. 1).

In the crystal structure, molecules are linked into a three-dimensional network (Fig. 2) by intermolecular O—H···O and N—H···O hydrogen bonds (Table 1).

Experimental

The title compound was prepared by the Schiff base condensation of 2-hydroxy-3-ethoxybenzaldehyde (0.1 mol) and 4-hydroxy-3-methoxybenzohydrazide (0.1 mmol) in 95% 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 obtained by slow evaporation of a 95% ethanol solution at room temperature.

Refinement

The imino and water H atoms were located in a difference map and refined with N-H, O-H, and H···H distance restraints of 0.90 (1), 0.85 (1) and 1.37 (2) Å, respectively. Other H atoms were positioned geometrically (C-H = 0.93-0.97 Å, O-H = 0.82 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl and O).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The dashed line indicates a hydrogen bond.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C17H18N2O5·H2OF(000) = 736
Mr = 348.35Dx = 1.387 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2358 reflections
a = 9.4063 (11) Åθ = 2.3–24.5°
b = 10.0598 (12) ŵ = 0.11 mm1
c = 17.667 (2) ÅT = 298 K
β = 93.702 (2)°Block, colourless
V = 1668.3 (3) Å30.23 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer3606 independent reflections
Radiation source: fine-focus sealed tube2530 reflections with I > 2σ(I)
graphiteRint = 0.022
ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −12→6
Tmin = 0.976, Tmax = 0.979k = −12→12
9554 measured reflectionsl = −19→22

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0506P)2 + 0.153P] where P = (Fo2 + 2Fc2)/3
3606 reflections(Δ/σ)max = 0.001
239 parametersΔρmax = 0.14 e Å3
4 restraintsΔρmin = −0.18 e Å3

Special details

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)

xyzUiso*/Ueq
N10.10205 (14)0.58113 (13)0.92228 (7)0.0430 (3)
N20.02746 (14)0.49793 (13)0.87165 (7)0.0439 (3)
O10.33352 (11)0.69470 (12)0.98717 (7)0.0540 (3)
H10.28970.63770.96210.081*
O20.44363 (11)0.88030 (11)1.07376 (6)0.0500 (3)
O30.22665 (12)0.38467 (12)0.84788 (6)0.0540 (3)
O4−0.35636 (11)0.22118 (12)0.71623 (6)0.0519 (3)
O5−0.21352 (12)0.07248 (12)0.62606 (6)0.0495 (3)
H5−0.18320.08030.58380.074*
O60.87031 (16)0.12628 (18)0.49098 (7)0.0831 (5)
C10.09270 (16)0.76123 (14)1.00984 (8)0.0386 (4)
C20.23985 (16)0.77422 (14)1.02122 (8)0.0381 (3)
C30.29798 (17)0.87517 (15)1.06851 (8)0.0401 (4)
C40.20833 (19)0.95870 (16)1.10488 (9)0.0461 (4)
H40.24631.02601.13610.055*
C50.06202 (19)0.94300 (17)1.09513 (9)0.0491 (4)
H5A0.00240.99861.12070.059*
C60.00461 (18)0.84627 (16)1.04808 (9)0.0455 (4)
H6−0.09380.83711.04150.055*
C70.02778 (17)0.66469 (15)0.95732 (8)0.0432 (4)
H7−0.07080.66360.94890.052*
C80.09772 (16)0.40175 (15)0.83586 (8)0.0384 (4)
C90.01099 (15)0.31662 (14)0.78123 (8)0.0351 (3)
C10−0.13784 (16)0.31459 (14)0.77666 (8)0.0365 (3)
H10−0.18780.36860.80840.044*
C11−0.21102 (15)0.23219 (15)0.72488 (8)0.0366 (3)
C12−0.13654 (17)0.15245 (14)0.67632 (8)0.0377 (3)
C130.01011 (17)0.15321 (15)0.68193 (8)0.0420 (4)
H130.06020.09850.65060.050*
C140.08347 (16)0.23511 (15)0.73412 (8)0.0397 (4)
H140.18250.23510.73740.048*
C150.50926 (19)0.98456 (17)1.11853 (11)0.0572 (5)
H15A0.47960.98011.17010.069*
H15B0.48171.07051.09740.069*
C160.66733 (19)0.9667 (2)1.11801 (12)0.0642 (5)
H16A0.69310.88051.13790.096*
H16B0.71441.03401.14890.096*
H16C0.69580.97401.06700.096*
C17−0.44022 (17)0.30663 (19)0.75946 (10)0.0555 (5)
H17A−0.41950.28980.81250.083*
H17B−0.53940.29020.74660.083*
H17C−0.41840.39750.74840.083*
H2−0.0640 (12)0.519 (2)0.8616 (11)0.080*
H6A0.8271 (18)0.119 (2)0.4483 (7)0.080*
H6B0.9512 (13)0.161 (2)0.4869 (11)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0430 (8)0.0417 (7)0.0424 (7)−0.0028 (6)−0.0102 (6)−0.0046 (6)
N20.0378 (7)0.0425 (7)0.0495 (7)−0.0006 (6)−0.0130 (6)−0.0076 (6)
O10.0423 (7)0.0555 (7)0.0638 (8)0.0032 (6)−0.0008 (6)−0.0259 (6)
O20.0426 (7)0.0509 (7)0.0560 (7)−0.0028 (5)−0.0007 (5)−0.0188 (5)
O30.0348 (6)0.0661 (8)0.0591 (7)0.0020 (6)−0.0115 (5)−0.0130 (6)
O40.0321 (6)0.0615 (7)0.0616 (7)−0.0057 (5)−0.0012 (5)−0.0146 (6)
O50.0477 (7)0.0577 (7)0.0426 (6)−0.0144 (6)0.0003 (5)−0.0110 (5)
O60.0632 (9)0.1350 (14)0.0491 (7)−0.0436 (9)−0.0107 (7)0.0188 (8)
C10.0404 (9)0.0381 (8)0.0367 (8)0.0013 (7)−0.0030 (7)0.0019 (6)
C20.0421 (9)0.0359 (8)0.0360 (7)0.0038 (7)0.0012 (7)−0.0027 (6)
C30.0393 (9)0.0415 (8)0.0391 (8)0.0004 (7)−0.0014 (7)−0.0028 (7)
C40.0549 (11)0.0411 (9)0.0420 (8)0.0016 (8)−0.0001 (8)−0.0104 (7)
C50.0500 (10)0.0490 (10)0.0488 (9)0.0113 (8)0.0060 (8)−0.0058 (7)
C60.0416 (9)0.0481 (9)0.0465 (9)0.0043 (8)0.0008 (7)0.0004 (7)
C70.0396 (9)0.0448 (9)0.0442 (9)0.0001 (7)−0.0061 (7)0.0000 (7)
C80.0367 (9)0.0412 (9)0.0362 (8)−0.0015 (7)−0.0055 (7)0.0024 (6)
C90.0349 (8)0.0366 (8)0.0328 (7)−0.0019 (7)−0.0047 (6)0.0039 (6)
C100.0364 (8)0.0378 (8)0.0350 (7)0.0002 (7)−0.0006 (6)−0.0010 (6)
C110.0302 (8)0.0400 (8)0.0391 (8)−0.0041 (7)−0.0017 (6)0.0048 (6)
C120.0408 (8)0.0382 (8)0.0334 (7)−0.0085 (7)−0.0024 (6)0.0001 (6)
C130.0399 (9)0.0457 (9)0.0407 (8)−0.0014 (7)0.0057 (7)−0.0030 (7)
C140.0314 (8)0.0449 (9)0.0422 (8)−0.0019 (7)−0.0009 (7)0.0017 (7)
C150.0513 (11)0.0513 (10)0.0682 (11)−0.0078 (9)−0.0016 (9)−0.0219 (9)
C160.0497 (11)0.0614 (12)0.0804 (13)−0.0063 (9)−0.0032 (10)−0.0139 (10)
C170.0362 (9)0.0684 (12)0.0622 (11)0.0030 (9)0.0043 (8)−0.0016 (9)

Geometric parameters (Å, °)

N1—C71.278 (2)C5—H5A0.93
N1—N21.3827 (17)C6—H60.93
N2—C81.352 (2)C7—H70.93
N2—H20.891 (9)C8—C91.493 (2)
O1—C21.3589 (18)C9—C141.380 (2)
O1—H10.82C9—C101.397 (2)
O2—C31.3681 (19)C10—C111.384 (2)
O2—C151.4296 (18)C10—H100.93
O3—C81.2297 (18)C11—C121.396 (2)
O4—C111.3703 (17)C12—C131.377 (2)
O4—C171.422 (2)C13—C141.387 (2)
O5—C121.3700 (17)C13—H130.93
O5—H50.82C14—H140.93
O6—H6A0.836 (9)C15—C161.498 (2)
O6—H6B0.844 (9)C15—H15A0.97
C1—C21.392 (2)C15—H15B0.97
C1—C61.395 (2)C16—H16A0.96
C1—C71.450 (2)C16—H16B0.96
C2—C31.403 (2)C16—H16C0.96
C3—C41.378 (2)C17—H17A0.96
C4—C51.385 (2)C17—H17B0.96
C4—H40.93C17—H17C0.96
C5—C61.368 (2)
C7—N1—N2116.17 (13)C10—C9—C8123.32 (13)
C8—N2—N1119.54 (13)C11—C10—C9120.03 (14)
C8—N2—H2124.6 (13)C11—C10—H10120.0
N1—N2—H2115.6 (13)C9—C10—H10120.0
C2—O1—H1109.5O4—C11—C10124.89 (14)
C3—O2—C15117.38 (12)O4—C11—C12114.95 (12)
C11—O4—C17118.38 (12)C10—C11—C12120.16 (13)
C12—O5—H5109.5O5—C12—C13122.36 (14)
H6A—O6—H6B110.4 (17)O5—C12—C11118.08 (13)
C2—C1—C6119.25 (14)C13—C12—C11119.53 (13)
C2—C1—C7121.93 (14)C12—C13—C14120.30 (14)
C6—C1—C7118.79 (14)C12—C13—H13119.8
O1—C2—C1123.22 (13)C14—C13—H13119.8
O1—C2—C3116.79 (14)C9—C14—C13120.67 (14)
C1—C2—C3119.97 (14)C9—C14—H14119.7
O2—C3—C4125.84 (14)C13—C14—H14119.7
O2—C3—C2114.69 (13)O2—C15—C16107.56 (14)
C4—C3—C2119.48 (15)O2—C15—H15A110.2
C3—C4—C5120.36 (15)C16—C15—H15A110.2
C3—C4—H4119.8O2—C15—H15B110.2
C5—C4—H4119.8C16—C15—H15B110.2
C6—C5—C4120.45 (15)H15A—C15—H15B108.5
C6—C5—H5A119.8C15—C16—H16A109.5
C4—C5—H5A119.8C15—C16—H16B109.5
C5—C6—C1120.45 (16)H16A—C16—H16B109.5
C5—C6—H6119.8C15—C16—H16C109.5
C1—C6—H6119.8H16A—C16—H16C109.5
N1—C7—C1121.97 (14)H16B—C16—H16C109.5
N1—C7—H7119.0O4—C17—H17A109.5
C1—C7—H7119.0O4—C17—H17B109.5
O3—C8—N2121.72 (14)H17A—C17—H17B109.5
O3—C8—C9121.55 (14)O4—C17—H17C109.5
N2—C8—C9116.73 (13)H17A—C17—H17C109.5
C14—C9—C10119.27 (13)H17B—C17—H17C109.5
C14—C9—C8117.40 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.942.6529 (16)144
O5—H5···O6i0.821.812.6177 (17)170
O6—H6A···O3ii0.84 (1)1.96 (1)2.7908 (17)176 (2)
O6—H6B···O1iii0.84 (1)2.08 (1)2.8714 (18)157 (2)
N2—H2···O4iv0.89 (1)2.54 (2)3.1181 (17)123 (2)
N2—H2···O5iv0.89 (1)2.19 (1)3.0496 (18)163 (2)

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x−1/2, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2887).

References

  • Abdul Alhadi, A. A., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o908. [PMC free article] [PubMed]
  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • 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]
  • Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o189. [PMC free article] [PubMed]
  • Narayana, B., Siddaraju, B. P., Raju, C. R., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o3522.
  • Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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