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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1999.
Published online 2008 September 24. doi:  10.1107/S1600536808029334
PMCID: PMC2959369

(E)-N′-(4-Hydroxy­benzyl­idene)-2-methoxy­benzohydrazide

Abstract

The title compound, C15H14N2O3, exists in the E configuration with respect to the central methyl­idene unit. The dihedral angle between the two substituted benzene rings is 22.0 (2)°. Within the mol­ecule there is an intra­molecular N—H(...)O hydrogen bond involving the hydro­zide H atom and the O atom of the meth­oxy substituent on the adjacent phenyl ring. In the crystal structure, mol­ecules are linked through inter­molecular O—H(...)O hydrogen bonds, forming zigzag chains along the b direction.

Related literature

For bond-length data, see: Allen et al. (1987 [triangle]). For background on the biological properties of hydrazones, see: El-Tabl et al. (2008 [triangle]); Chen et al. (2008 [triangle]); Alvarez et al. (2008 [triangle]); Ventura & Martins (2008 [triangle]); Kalinowski et al. (2008 [triangle]). For related structures, see: Diao & Yu (2006 [triangle]); Shan et al. (2008 [triangle]); Fun et al. (2008 [triangle]); Yehye et al. (2008 [triangle]); Ejsmont et al. (2008 [triangle]); Han et al. (2006 [triangle]); Lu et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1999-scheme1.jpg

Experimental

Crystal data

  • C15H14N2O3
  • M r = 270.28
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1999-efi1.jpg
  • a = 13.113 (3) Å
  • b = 9.189 (2) Å
  • c = 22.110 (4) Å
  • V = 2664.2 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 (2) K
  • 0.10 × 0.10 × 0.08 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.991, T max = 0.992
  • 20705 measured reflections
  • 2899 independent reflections
  • 1656 reflections with I > 2σ(I)
  • R int = 0.084

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.136
  • S = 1.02
  • 2899 reflections
  • 186 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; 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/S1600536808029334/su2061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029334/su2061Isup2.hkl

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

Acknowledgments

The author gratefully acknowledges support from the National Natural Science Foundation of China (grant No. 50774016).

supplementary crystallographic information

Comment

Hydrazones derived from the reactions of aldehydes with hydrazides show potential biological properties (El-Tabl et al., 2008; Chen et al., 2008; Alvarez et al., 2008; Ventura & Martins, 2008; Kalinowski et al., 2008). In the last few years, a large number of hydrazones have been reported (Diao & Yu, 2006; Shan et al., 2008; Fun et al., 2008; Yehye et al., 2008; Ejsmont et al., 2008). As a continuous study, the crystal structure of the title compound, (I), is reported in this paper.

Compound (I) was prepared by the reaction of 4-hydroxybenzaldehyde and 2-methoxybenzohydrazide in methanol. The molecular structure of compound (I) is illustrated in Fig. 1. The C7—N1 bond length of 1.272 (3) Å indicates the presence of a typical C═N double bond. The molecule exists in the E configuration with respect to the methylidene unit (C7═N1), as observed in similar compounds (Han et al., 2006; Lu et al., 2008). The dihedral angle between the two substituted benzene rings is 22.02 (12)°, indicating that the molecule is not planar. In the 2-methoxyphenyl unit atom C15 deviates slightly from the mean plane of the benzene ring (C9–C14) by 0.097 (3) Å. The bond lengths are in normal ranges (Allen et al., 1987).

In the molecule there is an intramolecular N—H···O hydrogen bond (Table 1), and in the crystal structure symmetry related molecules are linked through intermolecular O—H···O hydrogen bonds (Table 1), forming zig-zag chains along the b direction (Fig. 2).

Experimental

2-Methoxybenzohydrazide (0.166 g, 1 mmol) was dissolved in ethanol (50 ml), then 4-hydroxybenzaldehyde (0.122 g, 1 mmol) was added slowly to the solution, and the mixture was heated at reflux with continuous stirring for 1 h. The solution was cooled to room temperature, yielding colorless crystallites. Recrystallization from absolute ethanol yielded block-like single crytals of compound (I).

Refinement

The NH H-atom (H2A) was located in a difference Fourier map and freely refined, with the N—H distance restrained to 0.90 (1) Å, and Uiso = 0.08 Å2. The remaining OH and C-bound H-atoms were included in calculated positions and treated as riding atoms: O—H = 0.82 Å with Uiso(H) = 1.5Ueq(O), and C—H = 0.93–0.96 Å, with Uiso(H) = 1.2 or 1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of compound (I), with 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The crystal packing of compound (I), viewed along the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C15H14N2O3F(000) = 1136
Mr = 270.28Dx = 1.348 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1422 reflections
a = 13.113 (3) Åθ = 2.4–24.5°
b = 9.189 (2) ŵ = 0.10 mm1
c = 22.110 (4) ÅT = 298 K
V = 2664.2 (10) Å3Block, colourless
Z = 80.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer2899 independent reflections
Radiation source: fine-focus sealed tube1656 reflections with I > 2σ(I)
graphiteRint = 0.084
ω scansθmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −16→16
Tmin = 0.991, Tmax = 0.992k = −11→11
20705 measured reflectionsl = −28→28

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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0456P)2 + 0.6248P] where P = (Fo2 + 2Fc2)/3
2899 reflections(Δ/σ)max < 0.001
186 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = −0.16 e Å3

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
O10.05041 (12)0.41453 (19)0.87757 (7)0.0566 (5)
H1−0.00770.44220.88500.085*
O20.12254 (12)1.04261 (19)0.58301 (7)0.0603 (5)
O30.43319 (11)1.01975 (19)0.60152 (7)0.0565 (5)
N10.18804 (13)0.8432 (2)0.66327 (8)0.0445 (5)
N20.25132 (14)0.9141 (2)0.62338 (8)0.0460 (5)
C10.18233 (16)0.6684 (2)0.74406 (10)0.0423 (6)
C20.23796 (17)0.5671 (3)0.77706 (10)0.0488 (6)
H20.30710.55550.76900.059*
C30.19308 (17)0.4837 (3)0.82142 (10)0.0493 (6)
H30.23190.41680.84300.059*
C40.09138 (16)0.4992 (2)0.83370 (9)0.0413 (6)
C50.03475 (17)0.5996 (3)0.80141 (11)0.0537 (7)
H5−0.03430.61120.80970.064*
C60.07971 (17)0.6823 (3)0.75726 (10)0.0527 (7)
H60.04050.74890.73580.063*
C70.23330 (17)0.7529 (3)0.69767 (10)0.0467 (6)
H70.30320.74040.69280.056*
C80.21358 (17)1.0145 (2)0.58522 (9)0.0415 (5)
C90.28755 (16)1.0927 (2)0.54622 (9)0.0409 (5)
C100.39297 (17)1.1018 (3)0.55572 (10)0.0440 (6)
C110.4525 (2)1.1908 (3)0.51948 (11)0.0585 (7)
H110.52241.19710.52630.070*
C120.4087 (2)1.2695 (3)0.47368 (12)0.0667 (8)
H120.44891.33050.45010.080*
C130.3060 (2)1.2592 (3)0.46224 (12)0.0642 (7)
H130.27691.31100.43050.077*
C140.24661 (19)1.1715 (3)0.49838 (10)0.0532 (6)
H140.17711.16470.49050.064*
C150.53806 (18)1.0379 (3)0.61787 (12)0.0671 (8)
H15A0.58051.01370.58400.101*
H15B0.55400.97500.65120.101*
H15C0.54991.13720.62940.101*
H2A0.3188 (8)0.900 (3)0.6214 (12)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0478 (10)0.0620 (11)0.0600 (10)0.0031 (9)0.0133 (8)0.0151 (9)
O20.0392 (10)0.0760 (13)0.0656 (11)0.0092 (9)0.0079 (8)0.0192 (10)
O30.0400 (9)0.0684 (12)0.0611 (10)−0.0044 (8)−0.0049 (8)0.0097 (9)
N10.0417 (11)0.0500 (12)0.0419 (10)−0.0011 (9)0.0048 (9)0.0008 (10)
N20.0366 (10)0.0537 (13)0.0477 (11)0.0013 (10)0.0096 (9)0.0093 (10)
C10.0372 (12)0.0498 (14)0.0400 (12)0.0021 (11)0.0026 (10)−0.0010 (11)
C20.0329 (12)0.0626 (17)0.0509 (14)0.0050 (11)0.0069 (10)0.0057 (13)
C30.0444 (14)0.0528 (16)0.0508 (14)0.0087 (12)0.0029 (11)0.0081 (12)
C40.0412 (13)0.0441 (14)0.0386 (12)−0.0025 (11)0.0044 (10)−0.0017 (11)
C50.0340 (12)0.0695 (18)0.0575 (15)0.0055 (12)0.0067 (11)0.0122 (13)
C60.0430 (14)0.0646 (18)0.0506 (14)0.0104 (12)0.0004 (11)0.0132 (13)
C70.0394 (13)0.0546 (16)0.0460 (13)0.0040 (12)0.0080 (10)0.0026 (12)
C80.0407 (13)0.0460 (14)0.0377 (12)0.0023 (11)0.0025 (10)−0.0014 (11)
C90.0436 (13)0.0385 (13)0.0407 (12)0.0015 (11)0.0049 (10)−0.0015 (11)
C100.0482 (14)0.0440 (14)0.0399 (12)−0.0019 (11)0.0030 (10)−0.0025 (11)
C110.0566 (16)0.0604 (18)0.0584 (16)−0.0162 (13)0.0065 (13)−0.0018 (14)
C120.083 (2)0.0601 (18)0.0573 (16)−0.0179 (16)0.0138 (15)0.0089 (15)
C130.082 (2)0.0573 (18)0.0537 (15)0.0071 (16)0.0087 (14)0.0144 (14)
C140.0518 (14)0.0564 (17)0.0514 (14)0.0062 (13)0.0036 (12)0.0038 (13)
C150.0461 (15)0.076 (2)0.0793 (19)−0.0062 (14)−0.0128 (14)−0.0078 (16)

Geometric parameters (Å, °)

O1—C41.355 (2)C5—H50.9300
O1—H10.8200C6—H60.9300
O2—C81.222 (3)C7—H70.9300
O3—C101.368 (3)C8—C91.484 (3)
O3—C151.432 (3)C9—C141.389 (3)
N1—C71.272 (3)C9—C101.401 (3)
N1—N21.375 (2)C10—C111.386 (3)
N2—C81.344 (3)C11—C121.371 (4)
N2—H2A0.895 (10)C11—H110.9300
C1—C61.383 (3)C12—C131.373 (4)
C1—C21.389 (3)C12—H120.9300
C1—C71.450 (3)C13—C141.377 (3)
C2—C31.377 (3)C13—H130.9300
C2—H20.9300C14—H140.9300
C3—C41.368 (3)C15—H15A0.9600
C3—H30.9300C15—H15B0.9600
C4—C51.383 (3)C15—H15C0.9600
C5—C61.370 (3)
C4—O1—H1109.5O2—C8—N2122.0 (2)
C10—O3—C15119.53 (19)O2—C8—C9120.8 (2)
C7—N1—N2114.27 (18)N2—C8—C9117.2 (2)
C8—N2—N1120.36 (19)C14—C9—C10117.7 (2)
C8—N2—H2A115.6 (18)C14—C9—C8116.2 (2)
N1—N2—H2A124.1 (18)C10—C9—C8125.9 (2)
C6—C1—C2117.5 (2)O3—C10—C11122.4 (2)
C6—C1—C7123.3 (2)O3—C10—C9117.3 (2)
C2—C1—C7119.2 (2)C11—C10—C9120.3 (2)
C3—C2—C1121.5 (2)C12—C11—C10120.1 (3)
C3—C2—H2119.2C12—C11—H11119.9
C1—C2—H2119.2C10—C11—H11119.9
C4—C3—C2120.0 (2)C11—C12—C13120.8 (3)
C4—C3—H3120.0C11—C12—H12119.6
C2—C3—H3120.0C13—C12—H12119.6
O1—C4—C3118.0 (2)C12—C13—C14119.2 (3)
O1—C4—C5122.7 (2)C12—C13—H13120.4
C3—C4—C5119.4 (2)C14—C13—H13120.4
C6—C5—C4120.4 (2)C13—C14—C9121.9 (2)
C6—C5—H5119.8C13—C14—H14119.0
C4—C5—H5119.8C9—C14—H14119.0
C5—C6—C1121.2 (2)O3—C15—H15A109.5
C5—C6—H6119.4O3—C15—H15B109.5
C1—C6—H6119.4H15A—C15—H15B109.5
N1—C7—C1123.9 (2)O3—C15—H15C109.5
N1—C7—H7118.1H15A—C15—H15C109.5
C1—C7—H7118.1H15B—C15—H15C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.90 (1)1.91 (2)2.620 (2)135 (2)
O1—H1···O2i0.821.902.700 (2)164

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2061).

References

  • 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.
  • Alvarez, C., Alvarez, R., Corchete, P., Lopez, J. L., Perez-Melero, C., Pelaez, R. & Medarde, M. (2008). Bioorg. Med. Chem.16, 5952–5961. [PubMed]
  • Bruker (2001). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Chen, J., Liu, F., Song, B.-A., Yang, S., Hu, D.-Y., Jin, H.-H., Chen, Z. & Xue, W. (2008). Chin. J. Org. Chem.28, 894–898.
  • Diao, C.-H. & Yu, M. (2006). Acta Cryst. E62, o5278–o5279.
  • Ejsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128. [PMC free article] [PubMed]
  • El-Tabl, A. S., El-Saied, F. A. & Al-Hakimi, A. N. (2008). J. Coord. Chem.61, 2380–2401.
  • Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707. [PMC free article] [PubMed]
  • Han, J.-R., Wang, X.-F., Zhen, X.-L., Tian, X. & Liu, S.-X. (2006). Acta Cryst. E62, o5572–o5573.
  • Kalinowski, D. S., Sharpe, P. C., Bernhardt, P. V. & Richardson, D. R. (2008). J. Med. Chem.51, 331–344. [PubMed]
  • Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008). Acta Cryst. E64, o1695. [PMC free article] [PubMed]
  • Shan, S., Tian, Y.-L., Wang, S.-H., Wang, W.-L. & Xu, Y.-L. (2008). Acta Cryst. E64, o1363. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Ventura, C. & Martins, F. (2008). J. Med. Chem.51, 612–624. [PubMed]
  • Yehye, W. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o960. [PMC free article] [PubMed]

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