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Acta Cryst. (2008). E64, o1682    [ doi:10.1107/S160053680802360X ]

N'-(4-Hydroxybenzylidene)-4-methoxybenzohydrazide

X. Bao and Y.-J. Wei

Abstract top

The title compound, C15H14N2O3, was prepared by the reaction of 4-hydroxybenzaldehyde and 4-methoxybenzohydrazide in methanol. The dihedral angle between the two benzene rings is 6.8 (1)°. The methoxy group is disordered over two orientations with occupancies of ca 0.63 and 0.37. In the major disorder component, the methoxy group is coplanar with the attached ring. In the crystal structure, the molecules are linked into a three-dimensional framework by intermolecular O-H...O and N-H...O hydrogen bonds.

Comment top

Schiff bases are readily synthesized by the reaction of aldehydes with primary amines (Akitsu & Einaga, 2006; Pradeep, 2005; Butcher et al., 2005; Habibi et al., 2007). We have reported a few Schiff bases and their complexes (Wei et al., 2008a,b; Wei et al., 2006; Wei & Wang, 2006; Zhu et al., 2007; Wang et al., 2006). In this paper, we report the crystal structure of a new Schiff base compound.

Bond lengths and angles in the title compound (Fig. 1) are comparable with those observed in other Schiff bases (Yehye et al., 2008; Odabaşoğlu et al., 2007; Yathirajan et al., 2007). The dihedral angle between the C1–C6 and C9–C14 phenyl rings is 6.8 (1)°, indicating that they are nearly coplanar. In the major disorder component, the methoxy group is coplanar with the attached ring [C15—O3—C12—C11 = -2.6 (6)°].

The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen bonds (Table 1). These hydrogen bonds link the molecules into a three-dimensional framework (Fig. 2).

Related literature top

For the synthesis of Schiff bases, see: Akitsu & Einaga (2006); Butcher et al. (2005); Habibi et al. (2007); Pradeep (2005). For related Schiff base compounds, see: Wang et al. (2006); Wei et al. (2006, 2008a,b); Wei & Wang (2006); Zhu et al. (2007). For related structures, see: Odabaşoğlu et al. (2007); Yathirajan et al. (2007); Yehye et al. (2008).

Experimental top

4-Hydroxybenzaldehyde (1.0 mmol, 122.1 mg) and 4-methoxybenzohydrazide (1.0 mmol, 166.2 mg) were added to methanol (30 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. After keeping the solution in air for 12 d, colourless needle-shaped crystals were formed.

Refinement top

H atoms were positioned geometrically (C–H = 0.93–0.96 Å, O–H = 0.82 Å, N–H = 0.86 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(O,Cmethyl). The methoxy group is disordered over two sites with occupancies of 0.630 (2) and 0.370 (2). The corresponding C—O distances in both disorder components were restrained to be equal. The displacement parameters of atoms O3, O3A, C15 and C15A were restrained to an approximate isotropic behaviour. The low resolution is caused by weak diffraction of the crystal.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 compounnd, showing 30% probability displacement ellipsoids. Both disorder components are shown.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed approximately along the a axis. Hydrogen bonds are shown as dashed lines. Only the major disorder component is shown.
N'-(4-Hydroxybenzylidene)-4-methoxybenzohydrazide top
Crystal data top
C15H14N2O3F000 = 1136
Mr = 270.28Dx = 1.328 Mg m−3
Orthorhombic, PbcaMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2798 reflections
a = 12.342 (2) Åθ = 2.4–24.1º
b = 7.854 (2) ŵ = 0.09 mm−1
c = 27.889 (3) ÅT = 296 (2) K
V = 2703.4 (9) Å3Cut from needle, colourless
Z = 80.23 × 0.20 × 0.20 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		2308 independent reflections
Radiation source: fine-focus sealed tube1591 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 296(2) Kθmax = 24.7º
ω scansθmin = 1.5º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→12
Tmin = 0.979, Tmax = 0.981k = −9→9
12214 measured reflectionsl = −32→29
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)] = 0.049H-atom parameters constrained
wR(F2) = 0.135  w = 1/[σ2(Fo2) + (0.0514P)2 + 1.0313P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2308 reflectionsΔρmax = 0.24 e Å−3
201 parametersΔρmin = −0.24 e Å−3
26 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C15H14N2O3V = 2703.4 (9) Å3
Mr = 270.28Z = 8
Orthorhombic, PbcaMo Kα
a = 12.342 (2) ŵ = 0.09 mm−1
b = 7.854 (2) ÅT = 296 (2) K
c = 27.889 (3) Å0.23 × 0.20 × 0.20 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer		2308 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1591 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.981Rint = 0.033
12214 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04926 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.04Δρmax = 0.24 e Å−3
2308 reflectionsΔρmin = −0.24 e Å−3
201 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*/UeqOcc. (<1)
O10.91965 (15)−0.0226 (3)0.86782 (6)0.0813 (6)
H10.97790.01150.87820.122*
O20.61634 (13)0.0498 (2)0.59539 (5)0.0645 (5)
N10.76203 (15)0.1620 (2)0.65728 (6)0.0591 (5)
N20.74642 (15)0.2399 (2)0.61337 (6)0.0599 (5)
H2A0.78480.32650.60510.072*
C10.86057 (18)0.1561 (3)0.73055 (8)0.0588 (6)
C20.7901 (2)0.0470 (3)0.75378 (8)0.0700 (7)
H20.72710.01230.73830.084*
C30.8111 (2)−0.0109 (4)0.79911 (8)0.0752 (8)
H30.7623−0.08380.81410.090*
C40.90430 (19)0.0382 (3)0.82278 (8)0.0596 (6)
C50.9763 (2)0.1447 (3)0.80018 (8)0.0653 (6)
H51.04010.17680.81550.078*
C60.9535 (2)0.2038 (3)0.75471 (8)0.0701 (7)
H61.00200.27770.73990.084*
C70.8374 (2)0.2223 (3)0.68288 (8)0.0673 (7)
H70.87920.31130.67090.081*
C80.67021 (18)0.1775 (3)0.58398 (7)0.0546 (6)
C90.65325 (19)0.2623 (3)0.53725 (8)0.0605 (6)
C100.5570 (2)0.2357 (4)0.51343 (10)0.0882 (9)
H100.50310.16930.52740.106*
C110.5400 (3)0.3083 (4)0.46835 (11)0.1097 (12)
H110.47470.29010.45250.132*
C120.6183 (4)0.4056 (4)0.44727 (10)0.1047 (12)
C130.7138 (3)0.4305 (4)0.47006 (9)0.0938 (10)
H130.76780.49530.45560.113*
C140.7314 (2)0.3606 (3)0.51443 (8)0.0735 (7)
H140.79730.37950.52970.088*
O30.6249 (4)0.4882 (5)0.40185 (13)0.0866 (14)0.630 (7)
C150.5326 (4)0.4557 (6)0.37318 (19)0.0891 (18)0.630 (7)
H15A0.53970.51420.34310.134*0.630 (7)
H15B0.46890.49530.38950.134*0.630 (7)
H15C0.52660.33550.36750.134*0.630 (7)
O3A0.5470 (5)0.4517 (9)0.40930 (19)0.092 (2)0.370 (7)
C15A0.6242 (10)0.5249 (18)0.3782 (4)0.123 (5)0.370 (7)
H15D0.58890.56320.34950.185*0.370 (7)
H15E0.67810.44160.37020.185*0.370 (7)
H15F0.65820.61990.39380.185*0.370 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0866 (13)0.0986 (14)0.0586 (10)−0.0037 (11)−0.0139 (9)0.0213 (10)
O20.0700 (10)0.0642 (10)0.0593 (9)−0.0056 (9)−0.0002 (8)0.0010 (8)
N10.0716 (12)0.0616 (12)0.0440 (10)−0.0018 (10)−0.0069 (9)0.0074 (9)
N20.0738 (12)0.0587 (11)0.0472 (10)−0.0070 (10)−0.0092 (10)0.0078 (8)
C10.0698 (15)0.0560 (13)0.0507 (12)−0.0037 (12)−0.0085 (11)0.0039 (11)
C20.0712 (16)0.0746 (17)0.0641 (14)−0.0120 (14)−0.0162 (12)0.0100 (13)
C30.0751 (16)0.0836 (19)0.0668 (15)−0.0157 (14)−0.0104 (13)0.0229 (14)
C40.0702 (15)0.0594 (14)0.0491 (13)0.0066 (12)−0.0070 (11)0.0040 (11)
C50.0717 (15)0.0651 (15)0.0591 (14)−0.0069 (13)−0.0155 (12)0.0025 (12)
C60.0786 (17)0.0702 (17)0.0615 (14)−0.0191 (13)−0.0114 (13)0.0109 (12)
C70.0794 (17)0.0673 (16)0.0553 (14)−0.0134 (13)−0.0090 (12)0.0096 (12)
C80.0612 (13)0.0529 (13)0.0498 (12)0.0038 (11)−0.0007 (11)−0.0037 (10)
C90.0812 (17)0.0507 (13)0.0495 (12)0.0051 (12)−0.0145 (12)−0.0050 (10)
C100.104 (2)0.0766 (19)0.0841 (19)−0.0048 (16)−0.0388 (17)0.0022 (15)
C110.142 (3)0.087 (2)0.099 (2)0.010 (2)−0.075 (2)−0.0072 (19)
C120.193 (4)0.0605 (18)0.0604 (18)0.013 (2)−0.040 (2)−0.0018 (14)
C130.155 (3)0.0744 (19)0.0519 (15)0.0010 (19)−0.0118 (18)0.0050 (13)
C140.103 (2)0.0662 (16)0.0512 (13)−0.0025 (15)−0.0111 (13)0.0014 (12)
O30.105 (3)0.090 (3)0.064 (2)−0.025 (2)−0.024 (2)0.0248 (19)
C150.115 (4)0.090 (3)0.063 (3)0.003 (3)−0.032 (3)0.010 (2)
O3A0.101 (5)0.116 (5)0.059 (4)0.009 (4)−0.019 (3)0.019 (3)
C15A0.137 (8)0.137 (8)0.095 (7)−0.006 (6)0.002 (7)0.043 (6)
Geometric parameters (Å, °) top
O1—C41.357 (2)C9—C101.377 (3)
O1—H10.82C9—C141.389 (3)
O2—C81.245 (3)C10—C111.396 (4)
N1—C71.265 (3)C10—H100.93
N1—N21.382 (2)C11—C121.365 (5)
N2—C81.340 (3)C11—H110.93
N2—H2A0.86C12—C131.354 (5)
C1—C61.382 (3)C12—O3A1.424 (6)
C1—C21.382 (3)C12—O31.426 (4)
C1—C71.456 (3)C13—C141.371 (3)
C2—C31.368 (3)C13—H130.93
C2—H20.93C14—H140.93
C3—C41.381 (3)O3—C151.415 (5)
C3—H30.93C15—H15A0.96
C4—C51.373 (3)C15—H15B0.96
C5—C61.379 (3)C15—H15C0.96
C5—H50.93O3A—C15A1.412 (8)
C6—H60.93C15A—H15D0.96
C7—H70.93C15A—H15E0.96
C8—C91.479 (3)C15A—H15F0.96
C4—O1—H1109.5C9—C10—C11120.1 (3)
C7—N1—N2115.9 (2)C9—C10—H10120.0
C8—N2—N1118.51 (19)C11—C10—H10120.0
C8—N2—H2A120.7C12—C11—C10120.7 (3)
N1—N2—H2A120.7C12—C11—H11119.6
C6—C1—C2117.5 (2)C10—C11—H11119.6
C6—C1—C7120.7 (2)C13—C12—C11119.7 (3)
C2—C1—C7121.7 (2)C13—C12—O3A148.3 (4)
C3—C2—C1121.3 (2)C11—C12—O3A91.4 (4)
C3—C2—H2119.3C13—C12—O3107.6 (3)
C1—C2—H2119.3C11—C12—O3132.7 (3)
C2—C3—C4120.5 (2)C12—C13—C14120.2 (3)
C2—C3—H3119.8C12—C13—H13119.9
C4—C3—H3119.8C14—C13—H13119.9
O1—C4—C5123.3 (2)C13—C14—C9121.8 (3)
O1—C4—C3117.4 (2)C13—C14—H14119.1
C5—C4—C3119.3 (2)C9—C14—H14119.1
C4—C5—C6119.7 (2)C15—O3—C12111.9 (4)
C4—C5—H5120.2O3—C15—H15A109.5
C6—C5—H5120.2O3—C15—H15B109.5
C5—C6—C1121.7 (2)H15A—C15—H15B109.5
C5—C6—H6119.1O3—C15—H15C109.5
C1—C6—H6119.1H15A—C15—H15C109.5
N1—C7—C1121.7 (2)H15B—C15—H15C109.5
N1—C7—H7119.1C15A—O3A—C1298.2 (8)
C1—C7—H7119.1O3A—C15A—H15D109.5
O2—C8—N2120.9 (2)O3A—C15A—H15E109.5
O2—C8—C9120.8 (2)H15D—C15A—H15E109.5
N2—C8—C9118.3 (2)O3A—C15A—H15F109.5
C10—C9—C14117.5 (2)H15D—C15A—H15F109.5
C10—C9—C8118.6 (2)H15E—C15A—H15F109.5
C14—C9—C8123.8 (2)
C7—N1—N2—C8177.7 (2)N2—C8—C9—C1423.2 (3)
C6—C1—C2—C30.4 (4)C14—C9—C10—C11−0.9 (4)
C7—C1—C2—C3−178.2 (2)C8—C9—C10—C11−177.4 (2)
C1—C2—C3—C4−0.3 (4)C9—C10—C11—C120.2 (5)
C2—C3—C4—O1179.4 (2)C10—C11—C12—C130.8 (5)
C2—C3—C4—C5−0.6 (4)C10—C11—C12—O3A−173.0 (4)
O1—C4—C5—C6−178.6 (2)C10—C11—C12—O3177.2 (4)
C3—C4—C5—C61.4 (4)C11—C12—C13—C14−1.0 (5)
C4—C5—C6—C1−1.3 (4)O3A—C12—C13—C14167.1 (6)
C2—C1—C6—C50.4 (4)O3—C12—C13—C14−178.3 (3)
C7—C1—C6—C5179.0 (2)C12—C13—C14—C90.3 (4)
N2—N1—C7—C1178.0 (2)C10—C9—C14—C130.6 (4)
C6—C1—C7—N1169.3 (2)C8—C9—C14—C13176.9 (2)
C2—C1—C7—N1−12.1 (4)C13—C12—O3—C15174.2 (4)
N1—N2—C8—O2−1.7 (3)C11—C12—O3—C15−2.5 (7)
N1—N2—C8—C9179.47 (18)O3A—C12—O3—C15−17.1 (5)
O2—C8—C9—C1020.6 (3)C13—C12—O3A—C15A22.4 (11)
N2—C8—C9—C10−160.5 (2)C11—C12—O3A—C15A−167.9 (7)
O2—C8—C9—C14−155.7 (2)O3—C12—O3A—C15A1.4 (8)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.153.007 (3)172
O1—H1···O2ii0.821.882.696 (2)170
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x+1/2, y, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.153.007 (3)172
O1—H1···O2ii0.821.882.696 (2)170
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x+1/2, y, −z+3/2.
Acknowledgements top

The authors thank the Natural Science Foundation, Education Office of Anhui Province, People's Republic of China, for research grant No. KJ2007A126ZC.

references
References top

Akitsu, T. & Einaga, Y. (2006). Acta Cryst. E62, o4315–o4317.

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Butcher, R. J., Basu Baul, T. S., Singh, K. S. & Smith, F. E. (2005). Acta Cryst. E61, o1007–o1009.

Habibi, M. H., Mokhtari, R., Harrington, R. W. & Clegg, W. (2007). Acta Cryst. E63, o2881.

Odabaşoğlu, M., Büyükgüngör, O., Narayana, B., Vijesh, A. M. & Yathirajan, H. S. (2007). Acta Cryst. E63, o1916–o1918.

Pradeep, C. P. (2005). Acta Cryst. E61, o3825–o3827.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

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

Wang, F.-W., Wei, Y.-J. & Zhu, Q.-Y. (2006). Chin. J. Struct. Chem. 25, 1179–1182.

Wei, Y.-J. & Wang, F.-W. (2006). Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 36, 723–727.

Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2006). Chin. J. Struct. Chem. 25, 1090–1094.

Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2008a). Acta Cryst. E64, m859–m860.

Wei, Y.-J., Wang, F.-W. & Zhu, Q.-Y. (2008b). Transition Met. Chem. 33, 543–546.

Yathirajan, H. S., Vijesh, A. M., Narayana, B., Sarojini, B. K. & Bolte, M. (2007). Acta Cryst. E63, o936–o938.

Yehye, W. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o1452.

Zhu, C.-G., Wei, Y.-J. & Wang, F.-W. (2007). Acta Cryst. E63, m3197–m3198.