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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1009.
Published online 2008 May 7. doi:  10.1107/S1600536808006077
PMCID: PMC2961635

(E)-N′-(2-Hydroxy­benzyl­idene)-3,4,5-trimethoxy­benzohydrazide

Abstract

The title compound, C17H18N2O5, was synthesized from 3,4,5-trimethoxy­benzohydrazide and 2-hydroxy­benzaldehyde. The dihedral angle between the planes of the two benzene rings is 29.9 (2)°. The crystal structure involves intra­molecular O—H(...)N, and inter­molecular N—H(...)O and C—H(...)O hydrogen bonds.

Related literature

For related literature, see: Yang et al. (1996 [triangle]); Nawar et al. (2000 [triangle]). Gardner et al. (1991 [triangle]); Labouta et al. (1989 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1009-scheme1.jpg

Experimental

Crystal data

  • C17H18N2O5
  • M r = 330.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1009-efi1.jpg
  • a = 15.348 (12) Å
  • b = 13.330 (11) Å
  • c = 8.299 (7) Å
  • β = 99.854 (16)°
  • V = 1673 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 273 (2) K
  • 0.10 × 0.06 × 0.04 mm

Data collection

  • Bruker APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.991, T max = 0.995
  • 8200 measured reflections
  • 2952 independent reflections
  • 1945 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.194
  • S = 1.00
  • 2952 reflections
  • 219 parameters
  • H-atom parameters constrained
  • Δρmax = 0.59 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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 I, global. DOI: 10.1107/S1600536808006077/at2541sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006077/at2541Isup2.hkl

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

Acknowledgments

This work was supported by the Natural Science Fund of Jiangsu Province (No. BK2006012).

supplementary crystallographic information

Comment

3,4,5-Trimethoxybenzohydrazide and their deviatives show moderate fungicidal and anti-bacterial activities (Gardner et al.,1991). The antibacterial activity of formylhydrazines and formylhydrazones has been reported by Labouta et al. (1989). Many derivatives of formylhydrazines have interesting biological properties. So we synthesized the title compound (I) and report here its crystal structure.

The molecular structure of (I) is shown in Fig. 1, where the dash lines indicate N–H···O and O—H···N hydrogen bonds (Table 2). The atoms C7, N1, N2, C8 and O2 almost share a same plane for its delocalized structure. The dihedral angle between the planes of the two phenyl rings is 29.9 (217)°.

In the crystal structure, there is a intramolecular O—H···N hydrogen bond and two intermolecular N—H···O and C—H···O hydrogen bonds.

Experimental

An ethanol solution (50 ml) of 3,4,5-trimethoxybenzohydrazide (0.01 mol) and 2-hydroxybenzaldehyde (0.01 mol) was refluxed and stirred for 4 h. The mixture was cooled and the resulting solid product, (I), was collected by filtration. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in THF.

Refinement

All H atoms bonded to the C atoms were placed geometrically at the distances of 0.93–0.96 Å and included in the refinement in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the carrier atom.

Figures

Fig. 1.
A view of the molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level.
Fig. 2.
The packing diagram for (I) showing three dimensional network formed via hydrogen bonding.

Crystal data

C17H18N2O5F000 = 696
Mr = 330.33Dx = 1.312 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2179 reflections
a = 15.348 (12) Åθ = 2.7–22.9º
b = 13.330 (11) ŵ = 0.10 mm1
c = 8.299 (7) ÅT = 273 (2) K
β = 99.854 (16)ºNeedle, colourless
V = 1673 (2) Å30.10 × 0.06 × 0.04 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer2952 independent reflections
Radiation source: fine-focus sealed tube1945 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.048
T = 273(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −14→18
Tmin = 0.991, Tmax = 0.995k = −14→15
8200 measured reflectionsl = −9→9

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.068  w = 1/[σ2(Fo2) + (0.09P)2 + 1.3P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.194(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.59 e Å3
2952 reflectionsΔρmin = −0.25 e Å3
219 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009 (2)
Secondary atom site location: difference Fourier map

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O10.56784 (18)0.60473 (18)0.8299 (3)0.0620 (7)
H10.60080.64240.79040.093*
O20.72936 (16)0.85318 (16)0.7297 (3)0.0523 (7)
O30.81393 (18)1.13644 (15)0.3448 (4)0.0684 (8)
O40.92560 (17)1.04300 (17)0.1799 (3)0.0613 (8)
O50.96337 (16)0.84707 (17)0.2246 (3)0.0586 (7)
N10.67460 (17)0.66256 (18)0.6249 (3)0.0390 (6)
N20.72254 (17)0.72742 (18)0.5423 (3)0.0412 (7)
H20.73670.70840.45120.049*
C10.5635 (2)0.5152 (2)0.7521 (4)0.0445 (8)
C20.6102 (2)0.4977 (2)0.6245 (4)0.0423 (8)
C30.6039 (2)0.4020 (2)0.5511 (4)0.0541 (9)
H30.63440.38880.46580.065*
C40.5525 (3)0.3270 (3)0.6047 (5)0.0643 (11)
H40.54970.26360.55740.077*
C50.5060 (3)0.3479 (3)0.7282 (5)0.0651 (11)
H50.47080.29830.76290.078*
C60.5108 (3)0.4403 (3)0.8012 (4)0.0602 (10)
H60.47850.45300.88430.072*
C70.6621 (2)0.5750 (2)0.5607 (4)0.0421 (8)
H70.68740.56020.46930.051*
C80.7475 (2)0.8195 (2)0.6011 (4)0.0379 (7)
C90.7992 (2)0.8781 (2)0.4960 (4)0.0368 (7)
C100.7841 (2)0.9807 (2)0.4799 (4)0.0441 (8)
H100.74611.01230.54000.053*
C110.8259 (2)1.0356 (2)0.3738 (4)0.0461 (8)
C120.8839 (2)0.9881 (2)0.2853 (4)0.0460 (8)
C130.9029 (2)0.8862 (2)0.3110 (4)0.0428 (8)
C140.8592 (2)0.8308 (2)0.4139 (4)0.0415 (8)
H140.87010.76240.42790.050*
C150.7580 (3)1.1888 (3)0.4353 (6)0.0807 (14)
H15A0.69951.16100.41190.121*
H15B0.75601.25840.40530.121*
H15C0.78061.18240.55010.121*
C160.8877 (3)1.0316 (3)0.0131 (6)0.0787 (14)
H16A0.88320.9615−0.01380.118*
H16B0.92431.0644−0.05380.118*
H16C0.82981.0611−0.00620.118*
C171.0023 (3)0.7532 (3)0.2783 (5)0.0656 (11)
H17A1.02690.75720.39250.098*
H17B1.04830.73750.21710.098*
H17C0.95800.70170.26130.098*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.085 (2)0.0474 (14)0.0639 (17)−0.0132 (13)0.0429 (14)−0.0088 (12)
O20.0821 (17)0.0435 (13)0.0395 (14)0.0001 (11)0.0339 (12)−0.0002 (10)
O30.0843 (19)0.0262 (12)0.108 (2)0.0009 (11)0.0555 (17)0.0053 (12)
O40.0757 (18)0.0431 (13)0.077 (2)−0.0130 (12)0.0470 (15)0.0080 (12)
O50.0677 (16)0.0472 (14)0.0734 (18)0.0114 (12)0.0475 (14)0.0096 (12)
N10.0488 (16)0.0375 (14)0.0352 (15)−0.0023 (11)0.0199 (12)0.0062 (11)
N20.0614 (17)0.0367 (14)0.0326 (15)−0.0051 (12)0.0283 (13)0.0024 (11)
C10.059 (2)0.0382 (17)0.0386 (19)−0.0069 (15)0.0148 (16)−0.0011 (14)
C20.0508 (19)0.0364 (16)0.0417 (19)−0.0023 (14)0.0135 (15)0.0034 (13)
C30.071 (2)0.0403 (18)0.054 (2)−0.0005 (17)0.0179 (18)−0.0032 (16)
C40.087 (3)0.0363 (18)0.066 (3)−0.0093 (19)0.006 (2)−0.0028 (17)
C50.086 (3)0.051 (2)0.056 (2)−0.029 (2)0.009 (2)0.0073 (18)
C60.077 (3)0.062 (2)0.046 (2)−0.0220 (19)0.0245 (19)0.0042 (17)
C70.053 (2)0.0424 (18)0.0355 (18)0.0009 (14)0.0201 (15)0.0022 (14)
C80.0511 (19)0.0370 (16)0.0299 (17)0.0027 (14)0.0188 (14)0.0058 (13)
C90.0451 (18)0.0351 (16)0.0339 (17)−0.0007 (13)0.0169 (14)0.0011 (12)
C100.051 (2)0.0367 (17)0.051 (2)−0.0017 (14)0.0265 (16)−0.0048 (14)
C110.057 (2)0.0260 (15)0.061 (2)−0.0032 (14)0.0271 (17)0.0020 (14)
C120.053 (2)0.0320 (16)0.060 (2)−0.0071 (14)0.0305 (17)0.0021 (14)
C130.0484 (19)0.0369 (17)0.050 (2)0.0004 (14)0.0271 (16)0.0015 (14)
C140.053 (2)0.0328 (16)0.0429 (19)0.0012 (14)0.0213 (15)0.0014 (13)
C150.093 (3)0.0329 (19)0.128 (4)0.0065 (19)0.053 (3)−0.003 (2)
C160.090 (3)0.079 (3)0.077 (3)−0.001 (2)0.044 (3)0.033 (2)
C170.065 (2)0.069 (2)0.070 (3)0.024 (2)0.031 (2)0.009 (2)

Geometric parameters (Å, °)

O1—C11.353 (4)C5—H50.9300
O1—H10.8200C6—H60.9300
O2—C81.233 (3)C7—H70.9300
O3—C111.373 (4)C8—C91.496 (4)
O3—C151.417 (4)C9—C141.387 (4)
O4—C121.379 (4)C9—C101.390 (4)
O4—C161.415 (5)C10—C111.384 (4)
O5—C131.369 (3)C10—H100.9300
O5—C171.424 (4)C11—C121.398 (4)
N1—C71.284 (4)C12—C131.399 (4)
N1—N21.389 (3)C13—C141.386 (4)
N2—C81.351 (4)C14—H140.9300
N2—H20.8600C15—H15A0.9600
C1—C61.389 (5)C15—H15B0.9600
C1—C21.396 (4)C15—H15C0.9600
C2—C31.410 (5)C16—H16A0.9600
C2—C71.456 (4)C16—H16B0.9600
C3—C41.393 (5)C16—H16C0.9600
C3—H30.9300C17—H17A0.9600
C4—C51.373 (5)C17—H17B0.9600
C4—H40.9300C17—H17C0.9600
C5—C61.369 (5)
C1—O1—H1109.5C10—C9—C8118.3 (3)
C11—O3—C15117.7 (3)C11—C10—C9119.6 (3)
C12—O4—C16113.9 (3)C11—C10—H10120.2
C13—O5—C17117.1 (3)C9—C10—H10120.2
C7—N1—N2114.5 (2)O3—C11—C10124.5 (3)
C8—N2—N1121.9 (2)O3—C11—C12115.4 (3)
C8—N2—H2119.1C10—C11—C12120.1 (3)
N1—N2—H2119.1O4—C12—C11120.0 (3)
O1—C1—C6118.5 (3)O4—C12—C13120.3 (3)
O1—C1—C2121.3 (3)C11—C12—C13119.6 (3)
C6—C1—C2120.2 (3)O5—C13—C14124.3 (3)
C1—C2—C3118.2 (3)O5—C13—C12115.6 (3)
C1—C2—C7122.8 (3)C14—C13—C12120.1 (3)
C3—C2—C7118.9 (3)C13—C14—C9119.5 (3)
C4—C3—C2120.8 (3)C13—C14—H14120.2
C4—C3—H3119.6C9—C14—H14120.2
C2—C3—H3119.6O3—C15—H15A109.5
C5—C4—C3119.2 (3)O3—C15—H15B109.5
C5—C4—H4120.4H15A—C15—H15B109.5
C3—C4—H4120.4O3—C15—H15C109.5
C6—C5—C4121.2 (3)H15A—C15—H15C109.5
C6—C5—H5119.4H15B—C15—H15C109.5
C4—C5—H5119.4O4—C16—H16A109.5
C5—C6—C1120.4 (3)O4—C16—H16B109.5
C5—C6—H6119.8H16A—C16—H16B109.5
C1—C6—H6119.8O4—C16—H16C109.5
N1—C7—C2122.9 (3)H16A—C16—H16C109.5
N1—C7—H7118.5H16B—C16—H16C109.5
C2—C7—H7118.5O5—C17—H17A109.5
O2—C8—N2123.5 (3)O5—C17—H17B109.5
O2—C8—C9122.3 (3)H17A—C17—H17B109.5
N2—C8—C9114.2 (2)O5—C17—H17C109.5
C14—C9—C10120.9 (3)H17A—C17—H17C109.5
C14—C9—C8120.8 (3)H17B—C17—H17C109.5
C7—N1—N2—C8−174.6 (3)C8—C9—C10—C11−175.1 (3)
O1—C1—C2—C3178.8 (3)C15—O3—C11—C103.0 (6)
C6—C1—C2—C3−1.5 (5)C15—O3—C11—C12−178.0 (3)
O1—C1—C2—C7−3.6 (5)C9—C10—C11—O3178.1 (3)
C6—C1—C2—C7176.1 (3)C9—C10—C11—C12−0.9 (5)
C1—C2—C3—C4−0.1 (5)C16—O4—C12—C11−102.2 (4)
C7—C2—C3—C4−177.8 (3)C16—O4—C12—C1381.3 (4)
C2—C3—C4—C51.5 (6)O3—C11—C12—O41.1 (5)
C3—C4—C5—C6−1.2 (6)C10—C11—C12—O4−179.9 (3)
C4—C5—C6—C1−0.4 (6)O3—C11—C12—C13177.6 (3)
O1—C1—C6—C5−178.5 (4)C10—C11—C12—C13−3.4 (5)
C2—C1—C6—C51.8 (6)C17—O5—C13—C14−18.9 (5)
N2—N1—C7—C2−177.2 (3)C17—O5—C13—C12163.4 (3)
C1—C2—C7—N15.6 (5)O4—C12—C13—O5−0.7 (5)
C3—C2—C7—N1−176.8 (3)C11—C12—C13—O5−177.1 (3)
N1—N2—C8—O2−0.7 (5)O4—C12—C13—C14−178.4 (3)
N1—N2—C8—C9179.5 (2)C11—C12—C13—C145.1 (5)
O2—C8—C9—C14143.6 (3)O5—C13—C14—C9179.9 (3)
N2—C8—C9—C14−36.7 (4)C12—C13—C14—C9−2.5 (5)
O2—C8—C9—C10−37.9 (4)C10—C9—C14—C13−1.8 (5)
N2—C8—C9—C10141.9 (3)C8—C9—C14—C13176.8 (3)
C14—C9—C10—C113.5 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.942.670 (4)147
N2—H2···O2i0.862.002.826 (4)161 (1)
C7—H7···O2i0.932.483.240 (5)139

Symmetry codes: (i) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2541).

References

  • Bruker (1997). SAINT and SMART Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Gardner, T. S., Weins, R. & Lee, J. (1991). J Org Chem 26, 1514–1530.
  • Labouta, I. M., Hassan, A. M., Aboulwafa, O. M. & Kader, O. (1989). Monatsh. Chem.120, 571–574.
  • Nawar, N. & Hosny, N. M. (2000). Transition Met. Chem.25, 1–8.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yang, Z. Y., Yang, R. D. & Yu, K. B. (1996). Polyhedron, 15, 3749–3753.

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