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Acta Cryst. (2007). E63, o2864    [ doi:10.1107/S1600536807021277 ]

4-Hydroxy-N'-(2-hydroxybenzylidene)benzohydrazide

X.-C. Lin, H. Yin and Y. Lin

Abstract top

In the title molecule, C14H12N2O3, the -N-C(=O)- and 2-(iminomethyl)phenol fragments are almost coplanar, with an r.m.s. deviation of 0.0308 Å. The dihedral angle between the mean planes of p-phenol and N'-(2-hydroxybenzylidene)formohydrazide is 20.95 (7)°. Intermolecular O-H...O hydrogen bonds link the molecules into zigzag chains running along the b axis. Weak intermolecular N-H...O hydrogen bonds stabilize these chains into a three-dimensional packing.

Comment top

The chemistry of aroylhydrazone compounds have recently attracted great interest(Xue et al., 2006), owing to their biological activities (Yang & Pan, 2004) and potential chelating functions (Qiu et al., 2006). We report here the synthesis and crystal structure of the title compound (I), obtained by the condensation of salicylhydrazide with 4-Hydroxybenzohydrazine.

The molecule structure of (I) is shown in Fig. 1. The N1, C7, O1 fragment is almost coplanar with the 2-(iminomethyl)phenol (C8—C13, O3, C14, N2) with an r.m.s. deviation of 0.0309 Å. The dihedral angle between the phenol (C1—C6, O2) and N'-(2-hydroxybenzylidene) formohydrazide (C8—C13, O3, C14, N2, N1, C7, O1) is 20.95 (7)°. There are one intramolecular hydrogen bond (O3—H03A···N2) and two intermolecular hydrogen bonds (O2—H02A···O1i (i: -x, y - 1/2, -z + 3/2) and N1—H1N···O3i (i: x, -y + 1/2, z - 1/2)) (Table 1). The intermolecular O—H···O hydrogen bonds link the molecules into zigzag chains running along the b axis. The weak intermolecular N—H···O hydrogen bonds stabilize the chains into a three-dimensional packing. (Fig. 2).

Related literature top

The chemistry of aroylhydrazone compounds, their biological activities and potential chelating functions were recently discussed by Xue & Liu (2006), Yang & Pan (2004) and Qiu et al. (2006), respectively.

Experimental top

An equimolar mixture of salicylhydrazide (15 mmol) and 4-Hydroxybenzohydrazine (15 mmol) in ethanol was refluxed in a round-bottomed flask for about 3 h. The resulting precipitate was collected by filtration and washed with methanol and diethylether. The product (0.0358 g) was dissolved in methanol (15 ml), and kept at room temperature for 8 d to obtain yellow single crystals.

Refinement top

Atoms H02A, H03A and H1N were located on a difference Fourier map and refined isotropically with bond restraints O—H =0.85 (2) Å and N—H =0.86 (2) Å. All other H atoms were positioned geometrically and treated as riding [C—H =0.93Å and Uiso(H)=1.2Ueq(C)].

Computing details top

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and 50% probability displacement ellipsoids. The intramolecular hydrogen bonds are shown as dashed lines.
[Figure 2] Fig. 2. Packing diagram of (I), viewed down the b axis, showing hydrogen-bonded three-dimensional network. Hydrogen bonds are indicated by dashed lines.
N'-(2-hydroxybenzylidene)-4-hydroxybenzohydrazide top
Crystal data top
C14H12N2O3F(000) = 536
Mr = 256.26Dx = 1.404 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 6169 reflections
a = 13.583 (8) Åθ = 3.1–27.5°
b = 8.237 (4) ŵ = 0.10 mm−1
c = 11.499 (8) ÅT = 293 K
β = 109.53 (2)°Needle, yellow
V = 1212.5 (13) Å30.26 × 0.10 × 0.08 mm
Z = 4
Data collection top
Rigaku Weissenberg IP
diffractometer		2776 independent reflections
Radiation source: rotor target1342 reflections with I > 2σ(I)
graphiteRint = 0.096
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(TEXRAY; Molecular Structure Corporation, 1999)		h = −17→17
Tmin = 0.988, Tmax = 0.992k = −10→9
11461 measured reflectionsl = −14→14
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)] = 0.058H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0481P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
2776 reflectionsΔρmax = 0.18 e Å−3
185 parametersΔρmin = −0.19 e Å−3
3 restraintsExtinction correction: SHELXL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0057 (16)
Crystal data top
C14H12N2O3V = 1212.5 (13) Å3
Mr = 256.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.583 (8) ŵ = 0.10 mm−1
b = 8.237 (4) ÅT = 293 K
c = 11.499 (8) Å0.26 × 0.10 × 0.08 mm
β = 109.53 (2)°
Data collection top
Rigaku Weissenberg IP
diffractometer		1342 reflections with I > 2σ(I)
Absorption correction: multi-scan
(TEXRAY; Molecular Structure Corporation, 1999)		Rint = 0.096
Tmin = 0.988, Tmax = 0.992θmax = 27.5°
11461 measured reflectionsStandard reflections: none
2776 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.058H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127Δρmax = 0.18 e Å−3
S = 0.99Δρmin = −0.19 e Å−3
2776 reflectionsAbsolute structure: ?
185 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
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
C10.17334 (16)−0.0018 (3)0.2802 (2)0.0383 (6)
C20.18908 (18)−0.0299 (3)0.1686 (2)0.0507 (7)
H2A0.24720.01440.15490.061*
C30.11982 (18)−0.1225 (3)0.0780 (2)0.0545 (7)
H3A0.1313−0.13970.00360.065*
C40.03341 (17)−0.1898 (3)0.0972 (2)0.0434 (6)
C50.01702 (17)−0.1645 (3)0.2085 (2)0.0451 (6)
H5A−0.0407−0.21010.22230.054*
C60.08618 (16)−0.0720 (3)0.2981 (2)0.0412 (6)
H6A0.0747−0.05580.37260.049*
C70.24335 (16)0.0966 (3)0.3817 (2)0.0385 (6)
C80.57374 (16)0.3308 (3)0.5743 (2)0.0358 (6)
C90.54584 (18)0.4014 (3)0.6690 (2)0.0397 (6)
C100.6200 (2)0.4887 (3)0.7614 (2)0.0506 (7)
H10A0.60170.53620.82470.061*
C110.7198 (2)0.5046 (3)0.7592 (3)0.0550 (7)
H11A0.76890.56200.82180.066*
C120.7483 (2)0.4377 (3)0.6669 (3)0.0554 (8)
H12A0.81600.45070.66580.067*
C130.67605 (17)0.3508 (3)0.5753 (2)0.0472 (7)
H13A0.69580.30440.51270.057*
C140.50090 (17)0.2387 (3)0.4760 (2)0.0388 (6)
H14A0.52170.19840.41230.047*
O10.21602 (11)0.1535 (2)0.46486 (16)0.0491 (5)
O2−0.03193 (14)−0.2793 (2)0.00421 (18)0.0579 (5)
H02A−0.087 (2)−0.303 (4)0.021 (3)0.118 (14)*
O30.44705 (14)0.3907 (2)0.67470 (18)0.0525 (5)
H03A0.4119 (18)0.337 (3)0.612 (2)0.058 (9)*
N10.34201 (14)0.1221 (3)0.3811 (2)0.0424 (5)
H1N0.3640 (18)0.088 (3)0.322 (2)0.057 (8)*
N20.40823 (14)0.2122 (2)0.47586 (17)0.0381 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0326 (12)0.0429 (14)0.0403 (15)0.0015 (11)0.0134 (11)0.0067 (12)
C20.0384 (13)0.0720 (18)0.0465 (17)−0.0132 (13)0.0206 (12)−0.0032 (15)
C30.0463 (14)0.080 (2)0.0426 (16)−0.0140 (14)0.0224 (12)−0.0061 (15)
C40.0363 (13)0.0486 (15)0.0448 (16)−0.0020 (12)0.0131 (11)−0.0029 (13)
C50.0373 (13)0.0503 (15)0.0538 (18)−0.0060 (12)0.0233 (12)−0.0014 (14)
C60.0388 (13)0.0471 (14)0.0412 (15)0.0002 (11)0.0178 (11)0.0024 (12)
C70.0340 (12)0.0462 (14)0.0360 (15)0.0008 (11)0.0128 (11)0.0070 (12)
C80.0359 (12)0.0409 (13)0.0309 (13)0.0018 (11)0.0115 (10)0.0002 (11)
C90.0452 (13)0.0423 (13)0.0363 (15)0.0036 (12)0.0199 (11)0.0059 (12)
C100.0715 (18)0.0478 (15)0.0346 (16)−0.0013 (14)0.0204 (14)−0.0052 (13)
C110.0545 (16)0.0611 (17)0.0409 (16)−0.0129 (14)0.0046 (13)−0.0038 (14)
C120.0444 (14)0.0650 (18)0.0537 (19)−0.0068 (14)0.0121 (14)−0.0076 (15)
C130.0384 (13)0.0575 (16)0.0466 (16)−0.0038 (12)0.0155 (12)−0.0084 (13)
C140.0386 (13)0.0450 (14)0.0366 (15)−0.0008 (11)0.0175 (11)−0.0044 (11)
O10.0383 (9)0.0713 (12)0.0406 (11)−0.0005 (8)0.0169 (8)−0.0042 (9)
O20.0492 (11)0.0751 (13)0.0523 (13)−0.0176 (10)0.0208 (10)−0.0174 (10)
O30.0529 (11)0.0667 (13)0.0468 (12)−0.0032 (10)0.0287 (9)−0.0084 (11)
N10.0357 (11)0.0536 (13)0.0392 (13)−0.0056 (10)0.0144 (10)−0.0074 (11)
N20.0350 (10)0.0467 (12)0.0324 (11)−0.0026 (9)0.0111 (9)−0.0012 (10)
Geometric parameters (Å, °) top
C1—C21.389 (4)C8—C141.443 (3)
C1—C61.393 (3)C9—O31.368 (3)
C1—C71.477 (3)C9—C101.395 (3)
C2—C31.377 (3)C10—C111.370 (4)
C2—H2A0.9300C10—H10A0.9300
C3—C41.381 (3)C11—C121.362 (4)
C3—H3A0.9300C11—H11A0.9300
C4—O21.356 (3)C12—C131.377 (3)
C4—C51.386 (3)C12—H12A0.9300
C5—C61.370 (3)C13—H13A0.9300
C5—H5A0.9300C14—N21.277 (3)
C6—H6A0.9300C14—H14A0.9300
C7—O11.229 (3)O2—H02A0.851 (18)
C7—N11.359 (3)O3—H03A0.847 (17)
C8—C91.394 (3)N1—N21.376 (3)
C8—C131.396 (3)N1—H1N0.875 (17)
C2—C1—C6117.9 (2)O3—C9—C8122.5 (2)
C2—C1—C7124.3 (2)O3—C9—C10117.8 (2)
C6—C1—C7117.8 (2)C8—C9—C10119.6 (2)
C3—C2—C1121.0 (2)C11—C10—C9120.1 (3)
C3—C2—H2A119.5C11—C10—H10A119.9
C1—C2—H2A119.5C9—C10—H10A119.9
C2—C3—C4120.2 (3)C12—C11—C10121.1 (2)
C2—C3—H3A119.9C12—C11—H11A119.4
C4—C3—H3A119.9C10—C11—H11A119.4
O2—C4—C3117.3 (2)C11—C12—C13119.4 (3)
O2—C4—C5123.0 (2)C11—C12—H12A120.3
C3—C4—C5119.7 (2)C13—C12—H12A120.3
C6—C5—C4119.8 (2)C12—C13—C8121.4 (3)
C6—C5—H5A120.1C12—C13—H13A119.3
C4—C5—H5A120.1C8—C13—H13A119.3
C5—C6—C1121.5 (2)N2—C14—C8120.6 (2)
C5—C6—H6A119.3N2—C14—H14A119.7
C1—C6—H6A119.3C8—C14—H14A119.7
O1—C7—N1120.0 (2)C4—O2—H02A110 (3)
O1—C7—C1122.8 (2)C9—O3—H03A105.8 (19)
N1—C7—C1117.1 (2)C7—N1—N2117.6 (2)
C9—C8—C13118.3 (2)C7—N1—H1N123.3 (16)
C9—C8—C14122.4 (2)N2—N1—H1N119.0 (16)
C13—C8—C14119.2 (2)C14—N2—N1118.5 (2)
C6—C1—C2—C30.9 (4)C13—C8—C9—C10−0.2 (3)
C7—C1—C2—C3−179.6 (2)C14—C8—C9—C10179.9 (2)
C1—C2—C3—C4−0.3 (4)O3—C9—C10—C11−179.2 (2)
C2—C3—C4—O2179.8 (2)C8—C9—C10—C11−0.2 (4)
C2—C3—C4—C5−0.3 (4)C9—C10—C11—C120.7 (4)
O2—C4—C5—C6−179.7 (2)C10—C11—C12—C13−0.9 (4)
C3—C4—C5—C60.5 (4)C11—C12—C13—C80.6 (4)
C4—C5—C6—C10.1 (4)C9—C8—C13—C120.0 (4)
C2—C1—C6—C5−0.8 (3)C14—C8—C13—C12179.9 (2)
C7—C1—C6—C5179.7 (2)C9—C8—C14—N2−3.3 (4)
C2—C1—C7—O1161.2 (2)C13—C8—C14—N2176.8 (2)
C6—C1—C7—O1−19.3 (3)O1—C7—N1—N20.1 (3)
C2—C1—C7—N1−19.4 (3)C1—C7—N1—N2−179.32 (19)
C6—C1—C7—N1160.1 (2)C8—C14—N2—N1−179.2 (2)
C13—C8—C9—O3178.8 (2)C7—N1—N2—C14−179.3 (2)
C14—C8—C9—O3−1.1 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H02A···O1i0.85 (2)1.85 (2)2.698 (3)172 (4)
O3—H03A···N20.85 (2)1.86 (2)2.620 (3)149 (3)
N1—H1N···O3ii0.88 (2)2.33 (2)3.153 (3)156 (2)
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H02A···O1i0.85 (2)1.85 (2)2.698 (3)172 (4)
O3—H03A···N20.85 (2)1.86 (2)2.620 (3)149 (3)
N1—H1N···O3ii0.88 (2)2.33 (2)3.153 (3)156 (2)
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2.
Acknowledgements top

The authors acknowledge financial support from the Science Foundation of Fujian Province, China (grant No. 2001BA804A26–09) and the Foundation of Fuzhou University (grant No. 2006-XY-3).

references
References top

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