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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 10| October 2008| Page o1999
doi:10.1107/S1600536808029334

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

Xue-Hui Zhana*

aCollege of Chemistry and Biological Engineering, Changsha University of Science and Technology, Changsha 410076, People's Republic of China
*Correspondence e-mail: zhanxueh@163.com

(Received 4 September 2008; accepted 12 September 2008; online 24 September 2008)

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[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.]). For background on the biological properties of hydrazones, see: El-Tabl et al. (2008[El-Tabl, A. S., El-Saied, F. A. & Al-Hakimi, A. N. (2008). J. Coord. Chem. 61, 2380-2401.]); Chen et al. (2008[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.]); Alvarez et al. (2008[Alvarez, C., Alvarez, R., Corchete, P., Lopez, J. L., Perez-Melero, C., Pelaez, R. & Medarde, M. (2008). Bioorg. Med. Chem. 16, 5952-5961.]); Ventura & Martins (2008[Ventura, C. & Martins, F. (2008). J. Med. Chem. 51, 612-624.]); Kalinowski et al. (2008[Kalinowski, D. S., Sharpe, P. C., Bernhardt, P. V. & Richardson, D. R. (2008). J. Med. Chem. 51, 331-344.]). For related structures, see: Diao & Yu (2006[Diao, C.-H. & Yu, M. (2006). Acta Cryst. E62, o5278-o5279.]); Shan et al. (2008[Shan, S., Tian, Y.-L., Wang, S.-H., Wang, W.-L. & Xu, Y.-L. (2008). Acta Cryst. E64, o1363.]); Fun et al. (2008[Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707.]); Yehye et al. (2008[Yehye, W. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o960.]); Ejsmont et al. (2008[Ejsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128.]); Han et al. (2006[Han, J.-R., Wang, X.-F., Zhen, X.-L., Tian, X. & Liu, S.-X. (2006). Acta Cryst. E62, o5572-o5573.]); Lu et al. (2008[Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008). Acta Cryst. E64, o1695.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14N2O3

  • Mr = 270.28

  • Orthorhombic, P b c a

  • 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[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.991, Tmax = 0.992

  • 20705 measured reflections

  • 2899 independent reflections

  • 1656 reflections with I > 2σ(I)

  • Rint = 0.084
Refinement

  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2A⋯O3 0.895 (10) 1.91 (2) 2.620 (2) 135 (2)
O1—H1⋯O2i 0.82 1.90 2.700 (2) 164
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029334/su2061sup1.cif

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

checkCIF report


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 compound (I), with 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The crystal packing of compound (I), viewed along the a axis. Hydrogen bonds are shown as dashed lines.
(E)-N'-(4-Hydroxybenzylidene)-2-methoxybenzohydrazide top
Crystal data top
C15H14N2O3F(000) = 1136
Mr = 270.28Dx = 1.348 Mg m−3
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 mm−1
c = 22.110 (4) ÅT = 298 K
V = 2664.2 (10) Å3Block, colourless
Z = 80.10 × 0.10 × 0.08 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		2899 independent reflections
Radiation source: fine-focus sealed tube1656 reflections with I > 2σ(I)
Graphite monochromatorRint = 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 top
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 = 1.02 w = 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 Å−3
1 restraintΔρmin = −0.16 e Å−3
Crystal data top
C15H14N2O3V = 2664.2 (10) Å3
Mr = 270.28Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 13.113 (3) ŵ = 0.10 mm−1
b = 9.189 (2) ÅT = 298 K
c = 22.110 (4) Å0.10 × 0.10 × 0.08 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		2899 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		1656 reflections with I > 2σ(I)
Tmin = 0.991, Tmax = 0.992Rint = 0.084
20705 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0551 restraint
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.15 e Å−3
2899 reflectionsΔρmin = −0.16 e Å−3
186 parameters
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
O10.05041 (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) top
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, º) top
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, º) top
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 code: (i) −x, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC15H14N2O3
Mr270.28
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)13.113 (3), 9.189 (2), 22.110 (4)
V (Å3)2664.2 (10)
Z8
Radiation typeMo Kα
µ (mm−1)0.10
Crystal size (mm)0.10 × 0.10 × 0.08
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.991, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections		20705, 2899, 1656
Rint0.084
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.136, 1.02
No. of reflections2899
No. of parameters186
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.15, −0.16

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.895 (10)1.91 (2)2.620 (2)135 (2)
O1—H1···O2i0.821.902.700 (2)164
Symmetry code: (i) −x, y−1/2, −z+3/2.
 

Acknowledgements

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

References

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ISSN: 2056-9890
Volume 64| Part 10| October 2008| Page o1999
doi:10.1107/S1600536808029334
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