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Acta Cryst. (2008). E64, o1009    [ doi:10.1107/S1600536808006077 ]

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

Y.-M. Wang, Z.-D. Zhao, Y.-X. Chen and L.-W. Bi

Abstract top

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.

Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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. A view of the molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. The packing diagram for (I) showing three dimensional network formed via hydrogen bonding.
(E)-N'-(2-Hydroxybenzylidene)-3,4,5-trimethoxybenzohydrazide top
Crystal data top
C17H18N2O5F000 = 696
Mr = 330.33Dx = 1.312 Mg m−3
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 mm−1
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 top
Bruker APEX CCD area-detector
diffractometer		2952 independent reflections
Radiation source: fine-focus sealed tube1945 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.048
T = 273(2) Kθmax = 25.0º
φ 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 top
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 Å−3
2952 reflectionsΔρmin = −0.25 e Å−3
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
Crystal data top
C17H18N2O5V = 1673 (2) Å3
Mr = 330.33Z = 4
Monoclinic, P21/cMo Kα
a = 15.348 (12) ŵ = 0.10 mm−1
b = 13.330 (11) ÅT = 273 (2) K
c = 8.299 (7) Å0.10 × 0.06 × 0.04 mm
β = 99.854 (16)º
Data collection top
Bruker APEX CCD area-detector
diffractometer		2952 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1945 reflections with I > 2σ(I)
Tmin = 0.991, Tmax = 0.995Rint = 0.048
8200 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.068219 parameters
wR(F2) = 0.194H-atom parameters constrained
S = 1.00Δρmax = 0.59 e Å−3
2952 reflectionsΔρmin = −0.25 e Å−3
Special details top

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) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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

references
References top

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