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Acta Cryst. (2007). E63, o3672    [ doi:10.1107/S1600536807037014 ]

(E)-2-Hydroxy-N'-(3-hydroxy-4-methoxybenzylidene)benzohydrazide

Z.-G. Luo

Abstract top

The molecule of the title compound, C15H14N2O4, is roughly planar, except for the methyl H atoms, and displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two rings is 3.7 (2)°. The crystal structure is stabilized by intermolecular O-H...O and N-H...O hydrogen bonds.

Comment top

Recently, we have reported a few Schiff base complexes (Qiu, Luo et al., 2006; Qiu, Fang et al., 2006), As an extension of our work on the structural characterization of Schiff base compounds, the crystal structure of the title compound is reported here.

In the title compound, all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The C8═N2 bond length of 1.275 (2) Å conforms to the value for a double bond. The bond length of 1.337 (2) Å between N1 and C7 is greater than the value for a double bond, and less than the value for a single bond, because of conjugation in the molecule. The dihedral angle between the two rings is 3.7 (2)°.

The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen bonds. (Table 1 and Fig. 2)

Related literature top

For related literature, see: Allen et al. (1987); Qiu, Fang, Liu & Zhu (2006); Qiu, Luo, Yang & Liu (2006).

Experimental top

The reagents were commercial products and were used without further purification. 3-Hydroxy-4-methoxybenzaldehyde (0.1 mmol, 15.2 mg) and 2-hydroxybenzhydrazide (0.1 mmol, 15.2 mg) were dissolved in ethanol (15 ml). The reaction mixture was stirred for 30 minutes to give a clear solution. After allowing the resulting clear solution to stand at room temperature in air for 9 d, large colourless crystals were formed at the bottom of the vessel on slow evaporation of the solvent. The crystals were isolated, washed three times with ethanol and dried in a vacuum desiccator using anhydrous CaCl2 (yield 66%).

Refinement top

Atom H2, attached to O1, was located in a difference Fourier map and refined with an O—H distance restraint of 1.00 (2) Å. The other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H, N—H and O—H, distances of 0.93–0.96, 0.86 and 0.82 Å, respectively. and with Uiso(H) = 1.2Ueq(Csp2, N) or 1.5Ueq(methyl C, O).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

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 intramolecular hydrogen bonds.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the a axis. Dashed lines indicate intermolecular hydrogen bonds.
(E)—N'-(3-Hydroxy-4-methoxybenzylidene)-2-hydroxybenzohydrazide top
Crystal data top
C15H14N2O4F000 = 600
Mr = 286.28Dx = 1.446 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2865 reflections
a = 12.436 (3) Åθ = 4.2–26º
b = 7.1581 (14) ŵ = 0.11 mm−1
c = 15.048 (3) ÅT = 298 (2) K
β = 100.95 (3)ºBlock, colourless
V = 1315.2 (5) Å30.34 × 0.15 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX area-detector
diffractometer		3288 independent reflections
Radiation source: fine-focus sealed tube2008 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.030
T = 298(2) Kθmax = 28.5º
ω scansθmin = 2.8º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −16→16
Tmin = 0.96, Tmax = 0.99k = −9→9
11560 measured reflectionsl = −19→20
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of
independent and constrained refinement
R[F2 > 2σ(F2)] = 0.049  w = 1/[σ2(Fo2) + (0.0815P)2 + 0.0205P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.166(Δ/σ)max < 0.001
S = 1.10Δρmax = 0.28 e Å−3
3288 reflectionsΔρmin = −0.26 e Å−3
196 parametersExtinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009 (3)
Secondary atom site location: difference Fourier map
Crystal data top
C15H14N2O4V = 1315.2 (5) Å3
Mr = 286.28Z = 4
Monoclinic, P21/cMo Kα
a = 12.436 (3) ŵ = 0.11 mm−1
b = 7.1581 (14) ÅT = 298 (2) K
c = 15.048 (3) Å0.34 × 0.15 × 0.06 mm
β = 100.95 (3)º
Data collection top
Bruker SMART APEX area-detector
diffractometer		3288 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2008 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.99Rint = 0.030
11560 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049196 parameters
wR(F2) = 0.166H atoms treated by a mixture of
independent and constrained refinement
S = 1.10Δρmax = 0.28 e Å−3
3288 reflectionsΔρmin = −0.26 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 > 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
C11.19143 (13)0.11923 (19)0.43668 (9)0.0383 (3)
C21.30560 (13)0.1048 (2)0.46186 (11)0.0455 (4)
C31.35507 (15)0.1122 (2)0.55284 (12)0.0585 (5)
H31.43080.10220.56950.070*
C41.29249 (16)0.1342 (2)0.61828 (12)0.0569 (5)
H41.32660.13960.67880.068*
C51.18013 (14)0.1484 (2)0.59570 (10)0.0482 (4)
H51.13840.16310.64040.058*
C61.13091 (13)0.1405 (2)0.50587 (10)0.0426 (4)
H61.05510.14960.49040.051*
C71.13998 (13)0.10751 (19)0.34001 (9)0.0396 (4)
C80.87839 (12)0.1348 (2)0.20923 (9)0.0408 (4)
H80.84000.14610.25630.049*
C90.81933 (12)0.12816 (19)0.11589 (9)0.0384 (3)
C100.87688 (12)0.11754 (19)0.04428 (9)0.0382 (3)
H100.95300.11310.05670.046*
C110.82212 (12)0.11374 (19)−0.04359 (9)0.0364 (3)
C120.70753 (13)0.1193 (2)−0.06330 (10)0.0423 (4)
C130.64983 (13)0.1286 (2)0.00710 (11)0.0511 (4)
H130.57370.1317−0.00540.061*
C140.70586 (13)0.1333 (2)0.09602 (11)0.0470 (4)
H140.66680.14000.14290.056*
C210.54812 (16)0.1023 (3)−0.17878 (14)0.0823 (7)
H21A0.5231−0.0063−0.15120.123*
H21B0.52800.0921−0.24340.123*
H21C0.51500.2119−0.15890.123*
H21.3208 (19)0.093 (3)0.3393 (15)0.084 (7)*
N11.03213 (10)0.13674 (18)0.31683 (8)0.0444 (3)
H10.99410.16240.35740.053*
N20.98266 (11)0.12502 (17)0.22650 (8)0.0448 (4)
O11.37067 (10)0.08214 (18)0.39977 (9)0.0628 (4)
O21.19532 (9)0.06595 (17)0.28146 (7)0.0521 (3)
O30.88194 (8)0.10779 (14)−0.11127 (7)0.0461 (3)
H110.84030.1059−0.16050.069*
O40.66287 (9)0.11568 (16)−0.15360 (7)0.0558 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0423 (8)0.0413 (8)0.0314 (7)0.0009 (6)0.0073 (6)0.0002 (6)
C20.0432 (9)0.0495 (9)0.0437 (9)−0.0010 (7)0.0083 (7)0.0026 (6)
C30.0445 (10)0.0752 (12)0.0513 (10)−0.0006 (8)−0.0020 (8)0.0011 (8)
C40.0639 (12)0.0638 (11)0.0377 (9)−0.0005 (8)−0.0035 (8)0.0007 (7)
C50.0609 (10)0.0502 (9)0.0336 (8)0.0018 (7)0.0096 (7)−0.0002 (6)
C60.0441 (8)0.0483 (9)0.0357 (8)0.0017 (6)0.0080 (6)−0.0003 (6)
C70.0433 (8)0.0446 (8)0.0323 (8)0.0014 (6)0.0107 (6)0.0015 (6)
C80.0440 (9)0.0489 (9)0.0311 (7)−0.0006 (6)0.0112 (6)−0.0023 (6)
C90.0423 (8)0.0425 (8)0.0315 (7)−0.0020 (6)0.0094 (6)−0.0020 (6)
C100.0352 (8)0.0453 (8)0.0343 (8)−0.0006 (6)0.0072 (6)0.0011 (6)
C110.0375 (8)0.0395 (8)0.0337 (7)−0.0003 (6)0.0103 (6)0.0016 (5)
C120.0401 (8)0.0514 (9)0.0337 (8)0.0025 (6)0.0024 (6)−0.0034 (6)
C130.0347 (8)0.0733 (11)0.0461 (9)−0.0006 (7)0.0100 (7)−0.0076 (8)
C140.0410 (8)0.0640 (10)0.0385 (8)−0.0023 (7)0.0143 (7)−0.0058 (7)
C210.0435 (11)0.143 (2)0.0542 (12)0.0125 (11)−0.0075 (9)−0.0168 (11)
N10.0432 (7)0.0644 (9)0.0259 (6)0.0056 (6)0.0076 (5)−0.0030 (5)
N20.0479 (8)0.0582 (9)0.0281 (7)0.0047 (6)0.0068 (5)−0.0014 (5)
O10.0413 (7)0.0958 (10)0.0534 (8)0.0035 (6)0.0142 (6)0.0052 (6)
O20.0480 (7)0.0753 (8)0.0357 (6)0.0072 (5)0.0147 (5)−0.0020 (5)
O30.0422 (6)0.0685 (7)0.0285 (5)−0.0020 (5)0.0093 (4)0.0001 (4)
O40.0415 (7)0.0885 (9)0.0347 (6)0.0068 (5)0.0001 (5)−0.0039 (5)
Geometric parameters (Å, °) top
C1—C21.402 (2)C9—C101.404 (2)
C1—C61.404 (2)C10—C111.3678 (19)
C1—C71.476 (2)C10—H100.9300
C2—O11.357 (2)C11—O31.3712 (16)
C2—C31.391 (2)C11—C121.400 (2)
C3—C41.375 (2)C12—O41.3671 (18)
C3—H30.9300C12—C131.389 (2)
C4—C51.378 (3)C13—C141.387 (2)
C4—H40.9300C13—H130.9300
C5—C61.375 (2)C14—H140.9300
C5—H50.9300C21—O41.409 (2)
C6—H60.9300C21—H21A0.9600
C7—O21.2524 (16)C21—H21B0.9600
C7—N11.337 (2)C21—H21C0.9600
C8—N21.275 (2)N1—N21.3840 (17)
C8—C91.457 (2)N1—H10.8600
C8—H80.9300O1—H21.00 (2)
C9—C141.386 (2)O3—H110.8200
C2—C1—C6117.74 (14)C11—C10—H10119.7
C2—C1—C7119.30 (14)C9—C10—H10119.7
C6—C1—C7122.95 (14)C10—C11—O3118.55 (12)
O1—C2—C3118.17 (15)C10—C11—C12120.27 (13)
O1—C2—C1121.90 (14)O3—C11—C12121.17 (13)
C3—C2—C1119.93 (15)O4—C12—C13125.99 (14)
C4—C3—C2120.29 (16)O4—C12—C11114.52 (13)
C4—C3—H3119.9C13—C12—C11119.49 (14)
C2—C3—H3119.9C14—C13—C12119.95 (15)
C3—C4—C5121.15 (16)C14—C13—H13120.0
C3—C4—H4119.4C12—C13—H13120.0
C5—C4—H4119.4C9—C14—C13120.79 (14)
C6—C5—C4118.73 (15)C9—C14—H14119.6
C6—C5—H5120.6C13—C14—H14119.6
C4—C5—H5120.6O4—C21—H21A109.5
C5—C6—C1122.15 (15)O4—C21—H21B109.5
C5—C6—H6118.9H21A—C21—H21B109.5
C1—C6—H6118.9O4—C21—H21C109.5
O2—C7—N1120.78 (13)H21A—C21—H21C109.5
O2—C7—C1120.90 (14)H21B—C21—H21C109.5
N1—C7—C1118.29 (13)C7—N1—N2118.93 (12)
N2—C8—C9120.12 (13)C7—N1—H1120.5
N2—C8—H8119.9N2—N1—H1120.5
C9—C8—H8119.9C8—N2—N1116.24 (13)
C14—C9—C10118.82 (14)C2—O1—H2105.6 (12)
C14—C9—C8120.88 (14)C11—O3—H11109.5
C10—C9—C8120.30 (14)C12—O4—C21117.93 (14)
C11—C10—C9120.68 (14)
C6—C1—C2—O1179.36 (13)C8—C9—C10—C11−179.14 (13)
C7—C1—C2—O10.7 (2)C9—C10—C11—O3178.47 (11)
C6—C1—C2—C3−0.1 (2)C9—C10—C11—C12−0.4 (2)
C7—C1—C2—C3−178.83 (13)C10—C11—C12—O4179.66 (12)
O1—C2—C3—C4−179.71 (15)O3—C11—C12—O40.8 (2)
C1—C2—C3—C4−0.2 (2)C10—C11—C12—C130.0 (2)
C2—C3—C4—C50.3 (3)O3—C11—C12—C13−178.86 (13)
C3—C4—C5—C6−0.1 (2)O4—C12—C13—C14−179.32 (14)
C4—C5—C6—C1−0.2 (2)C11—C12—C13—C140.3 (2)
C2—C1—C6—C50.4 (2)C10—C9—C14—C13−0.2 (2)
C7—C1—C6—C5179.01 (13)C8—C9—C14—C13179.45 (13)
C2—C1—C7—O27.4 (2)C12—C13—C14—C9−0.2 (2)
C6—C1—C7—O2−171.25 (13)O2—C7—N1—N2−1.6 (2)
C2—C1—C7—N1−174.64 (12)C1—C7—N1—N2−179.59 (11)
C6—C1—C7—N16.7 (2)C9—C8—N2—N1178.54 (12)
N2—C8—C9—C14178.18 (13)C7—N1—N2—C8172.94 (13)
N2—C8—C9—C10−2.2 (2)C13—C12—O4—C21−6.4 (2)
C14—C9—C10—C110.5 (2)C11—C12—O4—C21173.87 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.262.9616 (16)138
O1—H2···O21.00 (2)1.65 (2)2.5424 (19)146.3 (19)
O3—H11···O2ii0.822.172.8451 (16)140
O3—H11···O40.822.232.6781 (17)115
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y, −z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.262.9616 (16)138
O1—H2···O21.00 (2)1.65 (2)2.5424 (19)146.3 (19)
O3—H11···O2ii0.822.172.8451 (16)140
O3—H11···O40.822.232.6781 (17)115
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y, −z.
Acknowledgements top

The author acknowledges the support of JingGangShan University.

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. S1–19.

Bruker (1998). SMART (Version 5.628) and SAINT (Version 6.02). Bruker AXS Inc., Madison, Winconsin, USA.

Qiu, X.-Y., Fang, X.-N., Liu, W.-S. & Zhu, H.-L. (2006). Acta Cryst. E62, o2685–o2686.

Qiu, X.-Y., Luo, Z.-G., Yang, S.-L. & Liu, W.-S. (2006). Acta Cryst. E62, o3531–o3532.

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

Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.