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Acta Cryst. (2009). E65, o2098    [ doi:10.1107/S1600536809030797 ]

N'-(2-Chlorobenzylidene)-4-hydroxybenzohydrazide

Y.-M. Hao

Abstract top

In the molecule of the title compound, C14H11ClN2O2, the dihedral angle between the benzene rings is 30.53 (4)°. In the crystal structure, intermolecular O-H...O and N-H...O hydrogen bonds link the molecules into a two-dimensional network. [pi]-[pi] contacts between benzene rings [centroid-centroid distance = 3.619 (1) Å] may further stabilize the structure. The crystal studied was found to be an inversion twin.

Comment top

Schiff base compounds are a class of important materials used in pharmaceutical and medicinal fields (Dao et al., 2000; Sriram et al., 2006; Karthikeyan et al., 2006). Schiff bases have also been used as versatile ligands in coordination chemistry (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). Recently, the crystal structures of a large number of Schiff base compounds have been reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). As a part of our ongoing investigation (Hao, 2009), we report herein the crystal structure of the title new Schiff base compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and B (C9-C14) are, of course, planar and the dihedral angle between them is A/B = 30.53 (4)°.

In the crystal structure, intermolecular O-H···O and N-H···O hydrogen bonds (Table 1) link the molecules into a two-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure. The π–π contact between the benzene rings, Cg1—Cg2i [symmetry code: (i) 1/2 + x, 1/2 - y, 1 - z, where Cg1 and Cg2 are centroids of the rings A (C1-C6) and B (C9-C14), respectively] may further stabilize the structure, with centroid-centroid distance of 3.619 (1) Å.

Related literature top

For general background, see: Ali et al. (2008); Dao et al. (2000); Kargar et al. (2009); Karthikeyan et al. (2006); Sriram et al. (2006); Yeap et al. (2009). For related structures, see: Eltayeb et al. (2008); Fun et al. (2009); Hao (2009); Nadeem et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, 2-chlorobenzaldehyde (0.1 mmol, 14.1 mg) and 4-hydroxybenzohydrazide (0.1 mmol, 15.2 mg) were refluxed in a methanol solution (30 ml) for 30 min to give a clear orange solution. Yellow block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.

Refinement top

Atom H2A (for NH) was located in a difference Fourier map and refined as riding in as-found relative position, Uiso(H) = 1.82Ueq(N). The remaining H atoms were positioned geometrically with O-H = 0.82 Å (for OH) and C-H = 0.93 for aromatic H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.5 for OH H and x = 1.2 for aromatic H atoms.

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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level
[Figure 2] Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.
N'-(2-Chlorobenzylidene)-4-hydroxybenzohydrazide top
Crystal data top
C14H11ClN2O2F(000) = 568
Mr = 274.70Dx = 1.427 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1016 reflections
a = 7.2851 (17) Åθ = 2.4–24.5°
b = 11.716 (3) ŵ = 0.30 mm−1
c = 14.978 (3) ÅT = 298 K
V = 1278.4 (5) Å3Block, yellow
Z = 40.20 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		2360 independent reflections
Radiation source: fine-focus sealed tube1617 reflections with I > 2σ(I)
graphiteRint = 0.045
ω scansθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −8→8
Tmin = 0.943, Tmax = 0.948k = −14→13
6989 measured reflectionsl = −16→18
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)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.0042P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2360 reflectionsΔρmax = 0.15 e Å−3
176 parametersΔρmin = −0.26 e Å−3
1 restraintAbsolute structure: Flack (1983), 963 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.45 (12)
Crystal data top
C14H11ClN2O2V = 1278.4 (5) Å3
Mr = 274.70Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 7.2851 (17) ŵ = 0.30 mm−1
b = 11.716 (3) ÅT = 298 K
c = 14.978 (3) Å0.20 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		2360 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1617 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 0.948Rint = 0.045
6989 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105Δρmax = 0.15 e Å−3
S = 1.02Δρmin = −0.26 e Å−3
2360 reflectionsAbsolute structure: Flack (1983), 963 Friedel pairs
176 parametersFlack parameter: 0.45 (12)
1 restraint
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cl10.01997 (17)0.34021 (7)1.00869 (6)0.0874 (4)
O10.1624 (4)0.92529 (17)1.04651 (12)0.0549 (6)
O20.1212 (3)1.16180 (18)0.67205 (12)0.0510 (6)
H20.18811.13580.63300.077*
N10.1278 (4)0.69987 (19)1.04360 (14)0.0437 (7)
N20.1146 (4)0.7642 (2)0.96676 (14)0.0440 (7)
C10.1105 (4)0.5194 (2)1.11448 (19)0.0410 (7)
C20.0682 (4)0.4040 (3)1.1104 (2)0.0512 (9)
C30.0627 (4)0.3368 (3)1.1861 (3)0.0616 (10)
H30.03350.25971.18170.074*
C40.1006 (5)0.3842 (3)1.2681 (2)0.0640 (10)
H40.09490.33941.31920.077*
C50.1472 (5)0.4985 (3)1.2746 (2)0.0588 (10)
H50.17490.53031.32980.071*
C60.1523 (4)0.5648 (3)1.19849 (19)0.0473 (8)
H60.18410.64151.20320.057*
C70.1054 (4)0.5933 (2)1.03614 (19)0.0439 (8)
H70.08550.56170.98000.053*
C80.1310 (4)0.8794 (2)0.97441 (17)0.0377 (7)
C90.1139 (4)0.9470 (2)0.89145 (17)0.0352 (7)
C100.1551 (4)0.9036 (2)0.80756 (17)0.0394 (7)
H100.18140.82630.80120.047*
C110.1576 (4)0.9737 (2)0.73349 (18)0.0416 (8)
H110.18760.94430.67770.050*
C120.1154 (4)1.0875 (2)0.74280 (16)0.0364 (7)
C130.0671 (4)1.1313 (2)0.82502 (17)0.0412 (7)
H130.03351.20750.83060.049*
C140.0692 (4)1.0614 (2)0.89873 (18)0.0409 (8)
H140.04011.09150.95440.049*
H2A0.074 (5)0.729 (3)0.9172 (14)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1341 (10)0.0427 (5)0.0854 (7)−0.0074 (6)−0.0095 (7)−0.0113 (5)
O10.0965 (19)0.0376 (12)0.0307 (11)0.0005 (12)−0.0119 (12)−0.0021 (10)
O20.0687 (16)0.0474 (13)0.0370 (11)0.0128 (13)0.0090 (11)0.0133 (10)
N10.0627 (18)0.0340 (15)0.0344 (13)−0.0020 (13)−0.0077 (14)0.0041 (11)
N20.067 (2)0.0337 (14)0.0308 (13)−0.0053 (13)−0.0059 (15)0.0026 (11)
C10.0396 (19)0.0398 (18)0.0435 (17)0.0050 (15)0.0051 (16)0.0050 (14)
C20.054 (2)0.0396 (19)0.0604 (19)0.0031 (15)0.0022 (18)0.0074 (16)
C30.052 (2)0.043 (2)0.089 (3)−0.0012 (18)0.008 (2)0.026 (2)
C40.057 (2)0.068 (3)0.067 (2)0.0149 (19)0.011 (2)0.0335 (19)
C50.064 (2)0.065 (3)0.048 (2)0.011 (2)0.0036 (19)0.0125 (18)
C60.049 (2)0.049 (2)0.0434 (18)0.0043 (16)0.0009 (17)0.0087 (16)
C70.056 (2)0.0378 (18)0.0378 (16)0.0035 (16)0.0009 (17)−0.0018 (14)
C80.0477 (19)0.0360 (16)0.0294 (15)−0.0026 (14)−0.0012 (15)0.0003 (12)
C90.0418 (18)0.0320 (16)0.0317 (14)−0.0026 (13)−0.0054 (15)0.0005 (12)
C100.052 (2)0.0340 (17)0.0325 (15)0.0014 (15)0.0012 (15)−0.0014 (13)
C110.052 (2)0.0432 (19)0.0297 (16)0.0042 (16)0.0012 (15)−0.0009 (13)
C120.0416 (18)0.0381 (17)0.0295 (15)0.0000 (15)−0.0015 (15)0.0083 (13)
C130.055 (2)0.0309 (16)0.0377 (16)0.0052 (14)0.0017 (15)0.0004 (13)
C140.057 (2)0.0345 (17)0.0316 (15)−0.0006 (14)0.0032 (15)−0.0025 (13)
Geometric parameters (Å, °) top
Cl1—C21.732 (3)C5—C61.380 (4)
O1—C81.228 (3)C5—H50.9300
O2—C121.372 (3)C6—H60.9300
O2—H20.8200C7—H70.9300
N1—N21.379 (3)C8—C91.479 (4)
N1—C71.264 (3)C9—C141.383 (4)
N2—C81.360 (3)C9—C101.388 (4)
N2—H2A0.90 (3)C10—C111.381 (4)
C1—C21.388 (4)C10—H100.9300
C1—C61.400 (4)C11—C121.375 (4)
C1—C71.459 (4)C11—H110.9300
C2—C31.381 (4)C12—C131.380 (4)
C3—C41.376 (5)C13—C141.375 (4)
C3—H30.9300C13—H130.9300
C4—C51.384 (5)C14—H140.9300
C4—H40.9300
C12—O2—H2109.5N1—C7—H7119.6
C7—N1—N2117.2 (2)C1—C7—H7119.6
N1—N2—H2A118 (2)O1—C8—N2121.7 (2)
C8—N2—N1117.8 (2)O1—C8—C9121.4 (2)
C8—N2—H2A123 (2)N2—C8—C9117.0 (2)
C2—C1—C6117.3 (3)C14—C9—C10118.5 (2)
C2—C1—C7122.5 (3)C14—C9—C8118.2 (2)
C6—C1—C7120.2 (3)C10—C9—C8123.1 (3)
C3—C2—C1121.7 (3)C11—C10—C9120.8 (3)
C3—C2—Cl1118.0 (3)C11—C10—H10119.6
C1—C2—Cl1120.3 (2)C9—C10—H10119.6
C4—C3—C2119.8 (3)C12—C11—C10119.5 (2)
C4—C3—H3120.1C12—C11—H11120.2
C2—C3—H3120.1C10—C11—H11120.2
C3—C4—C5120.2 (3)O2—C12—C11122.0 (2)
C3—C4—H4119.9O2—C12—C13117.5 (2)
C5—C4—H4119.9C11—C12—C13120.5 (2)
C6—C5—C4119.6 (3)C14—C13—C12119.5 (3)
C6—C5—H5120.2C14—C13—H13120.2
C4—C5—H5120.2C12—C13—H13120.2
C5—C6—C1121.5 (3)C13—C14—C9121.1 (3)
C5—C6—H6119.2C13—C14—H14119.5
C1—C6—H6119.2C9—C14—H14119.5
N1—C7—C1120.8 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.842.657 (3)179
N2—H2A···O2ii0.90 (3)2.11 (2)2.951 (3)157 (3)
Symmetry codes: (i) −x+1/2, −y+2, z−1/2; (ii) −x, y−1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.842.657 (3)179
N2—H2A···O2ii0.90 (3)2.11 (2)2.951 (3)157 (3)
Symmetry codes: (i) −x+1/2, −y+2, z−1/2; (ii) −x, y−1/2, −z+3/2.
Acknowledgements top

No acknowledgements.

references
References top

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