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Acta Cryst. (2008). E64, o1695    [ doi:10.1107/S160053680802521X ]

2-Methoxy-N'-(2-methoxybenzylidene)benzohydrazide

J.-F. Lu, S.-T. Min, X.-H. Ji and Z.-H. Dang

Abstract top

The title Schiff base compound, C16H16N2O3, was derived from the condensation of 2-methoxybenzaldehyde with 2-methoxybenzohydrazide in an ethanol solution. The dihedral angle between the two aromatic rings is 87.5 (3)°. In the crystal structure, the molecules are linked into chains running parallel to the a axis by intermolecular N-H...O hydrogen bonds.

Comment top

As part of our investigation of the crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b), we report here the crystal structure of the title new Schiff base compound.

In the title molecule (Fig. 1). the bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in related compounds (Nie, 2008; He, 2008; Shi et al., 2007). The dihedral angle between the two aromatic rings is 87.5 (3)°, indicating that they are almost perpendicular to one another.

In the crystal structure, the molecules are linked into chains (Fig. 2) running parallel to the a axis by intermolecular N–H···O hydrogen bonds (Table 1).

Related literature top

For related literature, see: Lu et al. (2008a,b); Nie (2008); He (2008); Shi et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the Schiff base condensation of 2-methoxybenzaldehyde (0.1 mol) and 2-methoxybenzohydrazide (0.1 mmol) in ethanol (50 ml). The excess ethanol was removed by distillation. The colorless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obatined by slow evaporation of an ethanol solution at room temperature.

Refinement top

The imino H atom was located in a difference map and refined with a N–H distance restraint of 0.90 (1) Å. The other H atoms were positioned geometrically (C–H = 0.93-0.96 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl). In the absence of significant anomalous scattering, Friedel pairs were merged.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the b axis. Dashed lines indicate hydrogen bonds.
2-Methoxy-N'-(2-methoxybenzylidene)benzohydrazide top
Crystal data top
C16H16N2O3F000 = 300
Mr = 284.31Dx = 1.297 Mg m−3
Monoclinic, P21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 744 reflections
a = 4.9998 (13) Åθ = 2.5–24.0º
b = 13.475 (4) ŵ = 0.09 mm−1
c = 10.824 (3) ÅT = 298 (2) K
β = 93.674 (4)ºBlock, colourless
V = 727.7 (4) Å30.30 × 0.30 × 0.28 mm
Z = 2
Data collection top
Bruker APEXII CCD area-detector
diffractometer		1647 independent reflections
Radiation source: fine-focus sealed tube1229 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.055
T = 298(2) Kθmax = 27.0º
ω scansθmin = 1.9º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −6→6
Tmin = 0.973, Tmax = 0.975k = −17→16
6081 measured reflectionsl = −13→13
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.095  w = 1/[σ2(Fo2) + (0.0297P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
1647 reflectionsΔρmax = 0.16 e Å−3
195 parametersΔρmin = −0.14 e Å−3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C16H16N2O3V = 727.7 (4) Å3
Mr = 284.31Z = 2
Monoclinic, P21Mo Kα
a = 4.9998 (13) ŵ = 0.09 mm−1
b = 13.475 (4) ÅT = 298 (2) K
c = 10.824 (3) Å0.30 × 0.30 × 0.28 mm
β = 93.674 (4)º
Data collection top
Bruker APEXII CCD area-detector
diffractometer		1647 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		1229 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.975Rint = 0.055
6081 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of
independent and constrained refinement
wR(F2) = 0.095Δρmax = 0.16 e Å−3
S = 1.11Δρmin = −0.14 e Å−3
1647 reflectionsAbsolute structure: ?
195 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Special details top

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) top
xyzUiso*/Ueq
O10.4130 (5)0.5063 (2)1.0258 (2)0.0579 (8)
O21.2673 (4)0.71624 (19)0.6930 (2)0.0436 (6)
O30.6361 (5)0.7245 (2)0.4683 (2)0.0513 (6)
N10.8931 (5)0.5916 (2)0.7771 (2)0.0357 (7)
N20.8339 (5)0.67811 (19)0.7116 (3)0.0354 (7)
C10.7337 (7)0.4561 (2)0.8904 (3)0.0371 (9)
C20.5766 (7)0.4321 (3)0.9892 (3)0.0426 (9)
C30.6008 (7)0.3398 (3)1.0439 (3)0.0501 (10)
H30.49530.32331.10860.060*
C40.7794 (8)0.2725 (3)1.0032 (4)0.0549 (11)
H40.79280.21021.04000.066*
C50.9407 (8)0.2954 (3)0.9081 (4)0.0537 (10)
H51.06450.24980.88180.064*
C60.9142 (7)0.3876 (3)0.8529 (3)0.0455 (9)
H61.02160.40360.78870.055*
C70.6996 (7)0.5520 (2)0.8295 (3)0.0377 (8)
H70.53530.58440.82910.045*
C81.0305 (6)0.7328 (2)0.6674 (3)0.0296 (7)
C90.9390 (6)0.8198 (2)0.5913 (3)0.0343 (8)
C100.7391 (6)0.8162 (3)0.4959 (3)0.0358 (8)
C110.6635 (7)0.9012 (3)0.4321 (3)0.0518 (10)
H110.52570.89900.37030.062*
C120.7913 (8)0.9890 (3)0.4597 (4)0.0606 (12)
H120.73841.04620.41680.073*
C130.9946 (8)0.9936 (3)0.5493 (4)0.0617 (12)
H131.08351.05330.56590.074*
C141.0677 (7)0.9096 (3)0.6151 (4)0.0478 (10)
H141.20590.91310.67670.057*
C150.2563 (8)0.4878 (4)1.1267 (4)0.0653 (12)
H15A0.14950.42951.11050.098*
H15B0.14100.54351.13850.098*
H15C0.37140.47781.20010.098*
C160.4372 (8)0.7167 (4)0.3692 (3)0.0712 (12)
H16A0.28210.75420.38850.107*
H16B0.38840.64830.35730.107*
H16C0.50660.74220.29490.107*
H20.662 (3)0.696 (3)0.696 (3)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0577 (16)0.0581 (19)0.0601 (19)0.0064 (15)0.0196 (15)0.0132 (15)
O20.0265 (12)0.0451 (14)0.0586 (14)0.0050 (12)−0.0024 (10)0.0062 (13)
O30.0604 (15)0.0471 (15)0.0439 (13)−0.0052 (14)−0.0149 (11)0.0053 (14)
N10.0391 (16)0.0318 (15)0.0356 (15)0.0028 (13)−0.0030 (13)0.0079 (13)
N20.0271 (14)0.0357 (16)0.0428 (16)0.0036 (13)−0.0018 (13)0.0124 (13)
C10.037 (2)0.038 (2)0.0354 (19)−0.0036 (16)−0.0070 (16)0.0053 (16)
C20.041 (2)0.046 (2)0.040 (2)−0.0060 (18)−0.0050 (18)0.0062 (18)
C30.054 (2)0.051 (3)0.045 (2)−0.011 (2)−0.0020 (18)0.0176 (19)
C40.069 (3)0.035 (2)0.058 (3)0.000 (2)−0.016 (2)0.018 (2)
C50.061 (3)0.043 (2)0.056 (3)0.0023 (19)−0.001 (2)0.001 (2)
C60.049 (2)0.042 (2)0.045 (2)−0.0021 (19)0.0002 (18)0.0085 (18)
C70.0336 (18)0.043 (2)0.0357 (19)0.0002 (16)−0.0008 (16)0.0078 (16)
C80.0279 (17)0.0279 (18)0.0332 (16)−0.0013 (15)0.0026 (13)−0.0029 (15)
C90.0317 (17)0.0346 (19)0.0377 (18)0.0046 (15)0.0098 (14)0.0017 (16)
C100.0368 (19)0.0353 (19)0.0357 (19)0.0037 (16)0.0051 (15)0.0015 (17)
C110.055 (2)0.056 (3)0.044 (2)0.008 (2)0.001 (2)0.013 (2)
C120.065 (3)0.046 (3)0.071 (3)0.007 (2)0.009 (2)0.027 (2)
C130.072 (3)0.039 (2)0.076 (3)−0.010 (2)0.014 (3)0.008 (2)
C140.048 (2)0.037 (2)0.058 (2)−0.0087 (19)0.0060 (19)0.003 (2)
C150.060 (3)0.083 (3)0.054 (3)−0.002 (3)0.012 (2)0.009 (2)
C160.077 (3)0.078 (3)0.055 (2)−0.014 (3)−0.023 (2)0.009 (3)
Geometric parameters (Å, °) top
O1—C21.367 (4)C6—H60.93
O1—C151.407 (4)C7—H70.93
O2—C81.220 (3)C8—C91.488 (4)
O3—C101.364 (4)C9—C141.387 (5)
O3—C161.419 (4)C9—C101.391 (4)
N1—C71.270 (4)C10—C111.378 (5)
N1—N21.387 (3)C11—C121.368 (5)
N2—C81.341 (4)C11—H110.93
N2—H20.901 (10)C12—C131.360 (5)
C1—C61.370 (5)C12—H120.93
C1—C21.405 (5)C13—C141.375 (5)
C1—C71.456 (4)C13—H130.93
C2—C31.380 (5)C14—H140.93
C3—C41.365 (5)C15—H15A0.96
C3—H30.93C15—H15B0.96
C4—C51.383 (5)C15—H15C0.96
C4—H40.93C16—H16A0.96
C5—C61.381 (5)C16—H16B0.96
C5—H50.93C16—H16C0.96
C2—O1—C15118.0 (3)C14—C9—C10118.1 (3)
C10—O3—C16118.0 (3)C14—C9—C8117.5 (3)
C7—N1—N2115.9 (3)C10—C9—C8124.3 (3)
C8—N2—N1120.5 (2)O3—C10—C11123.8 (3)
C8—N2—H2120 (3)O3—C10—C9115.9 (3)
N1—N2—H2120 (3)C11—C10—C9120.3 (3)
C6—C1—C2118.8 (3)C12—C11—C10120.0 (4)
C6—C1—C7121.6 (3)C12—C11—H11120.0
C2—C1—C7119.6 (3)C10—C11—H11120.0
O1—C2—C3125.0 (3)C13—C12—C11120.8 (4)
O1—C2—C1115.3 (3)C13—C12—H12119.6
C3—C2—C1119.7 (4)C11—C12—H12119.6
C4—C3—C2120.1 (4)C12—C13—C14119.6 (4)
C4—C3—H3120.0C12—C13—H13120.2
C2—C3—H3119.9C14—C13—H13120.2
C3—C4—C5121.1 (3)C13—C14—C9121.2 (4)
C3—C4—H4119.5C13—C14—H14119.4
C5—C4—H4119.5C9—C14—H14119.4
C6—C5—C4118.6 (4)O1—C15—H15A109.5
C6—C5—H5120.7O1—C15—H15B109.5
C4—C5—H5120.7H15A—C15—H15B109.5
C1—C6—C5121.6 (4)O1—C15—H15C109.5
C1—C6—H6119.2H15A—C15—H15C109.5
C5—C6—H6119.2H15B—C15—H15C109.5
N1—C7—C1120.3 (3)O3—C16—H16A109.5
N1—C7—H7119.9O3—C16—H16B109.5
C1—C7—H7119.9H16A—C16—H16B109.5
O2—C8—N2122.8 (3)O3—C16—H16C109.5
O2—C8—C9122.0 (3)H16A—C16—H16C109.5
N2—C8—C9115.1 (3)H16B—C16—H16C109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.90 (1)1.99 (1)2.873 (3)167 (4)
Symmetry codes: (i) x−1, y, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.90 (1)1.99 (1)2.873 (3)167 (4)
Symmetry codes: (i) x−1, y, z.
Acknowledgements top

The authors acknowledge Shaanxi University of Technology for the research fund.

references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.

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Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008b). Acta Cryst. E64, o???? (CI2647).

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Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.

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

Shi, X.-F., Liu, C.-Y., Liu, B. & Yuan, C.-C. (2007). Acta Cryst. E63, o1295–o1296.