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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o1864.
Published online 2008 September 6. doi:  10.1107/S1600536808027426
PMCID: PMC2959272

3-Hydr­oxy-N′-(2-hydroxy­benzyl­idene)benzohydrazide

Abstract

The title compound, C14H12N2O3, was synthesized by the condensation of salicylaldehyde with 3-hydroxy­benzo­hydrazide. The dihedral angle between the two benzene rings is 12.4 (2)°. The 2-hydr­oxy group forms an intra­molecular O—H(...)N hydrogen bond with the imide N atom. Mol­ecules are linked through inter­molecular O—H(...)O and N—H(...)O hydrogen bonds into a two-dimensional polymeric structure parallel to the ab plane.

Related literature

For related literature, see: Ali et al. (2005 [triangle]); Eltayeb et al. (2008 [triangle]); Habibi et al. (2007 [triangle]); Jing et al. (2006 [triangle]); Ling et al. (2008 [triangle]); Peng & You (2007 [triangle]); Peng & Zhou (2007 [triangle]); Peng, Ping & Song (2007 [triangle]); Peng, Yang & Zhou (2006 [triangle]); Peng, Zhou & Yang (2006 [triangle]); Yehye et al. (2008a [triangle],b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1864-scheme1.jpg

Experimental

Crystal data

  • C14H12N2O3
  • M r = 256.26
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1864-efi1.jpg
  • a = 14.405 (2) Å
  • b = 9.661 (1) Å
  • c = 17.905 (2) Å
  • V = 2491.8 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 (2) K
  • 0.23 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.978, T max = 0.981
  • 13415 measured reflections
  • 2720 independent reflections
  • 1869 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.118
  • S = 1.03
  • 2720 reflections
  • 177 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027426/gk2164sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027426/gk2164Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We acknowledge Changsha University of Science and Technology for research grants.

supplementary crystallographic information

Comment

Schiff bases derived from the condensation of aldehydes with primary amines play an important role in coordination chemistry (Ali et al., 2005; Eltayeb et al., 2008; Habibi et al., 2007). Recently, we have reported synthesis and crystal structure of some Schiff base complexes (Peng, Yang & Zhou, 2006; Peng, Zhou & Yang, 2006; Peng et al., 2007; Peng & You, 2007; Peng & Zhou, 2007). We report herein the crystal structure of the title compound, Fig. 1.

All the bond lengths are comparable to those observed in other similar compounds (Yehye et al., 2008a,b; Jing et al., 2006; Ling et al., 2008). The molecule is not planar and the dihedral angle between the two benzene rings is 12.4 (2)°. There is an intramolecular O–H···N hydrogen bond (Table 1) in each molecule of the compound. The molecules are linked through intermolecular O–H···O and N–H···O hydrogen bonds (Table 1), forming layers parallel to the ab plane (Fig. 2).

Experimental

3-Hydroxybenzohydrazide (0.1 mmol, 15.2 mg) and salicylaldehyde (0.1 mmol, 12.2 mg) were stirred at 318 K in methanol (10 ml) for 30 min. The filtrate was kept open to slowly evaporate for a few days, depositing colorless block-like crystals of the title compound.

Refinement

The atom H2 attached to N2 was located in a difference Fourier map and refined with N–H distance restrained to 0.90 (1) Å, and with Uiso set to 0.08 Å2. All H atoms bound to carbon and oxygen were refined using riding models with d(C–H) = 0.93 Å, d(O–H) = 0.82 Å, Uiso = 1.2Ueq(C) and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme and 30% probability displacement ellipsoids. H atoms are shown as spheres of arbitrary radii.
Fig. 2.
Packing diagram, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C14H12N2O3F(000) = 1072
Mr = 256.26Dx = 1.366 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3092 reflections
a = 14.405 (2) Åθ = 2.7–26.0°
b = 9.661 (1) ŵ = 0.10 mm1
c = 17.905 (2) ÅT = 298 K
V = 2491.8 (5) Å3Block, colorless
Z = 80.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer2720 independent reflections
Radiation source: fine-focus sealed tube1869 reflections with I > 2σ(I)
graphiteRint = 0.039
ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −15→18
Tmin = 0.978, Tmax = 0.981k = −11→12
13415 measured reflectionsl = −22→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0535P)2 + 0.3997P] where P = (Fo2 + 2Fc2)/3
2720 reflections(Δ/σ)max < 0.001
177 parametersΔρmax = 0.13 e Å3
1 restraintΔρmin = −0.18 e Å3

Special details

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)

xyzUiso*/Ueq
O10.16163 (8)1.20579 (14)0.04590 (8)0.0677 (4)
H10.18291.14270.07130.102*
O20.33625 (7)0.98665 (12)0.15618 (6)0.0524 (3)
O30.56381 (7)0.66767 (12)0.27314 (7)0.0548 (3)
H30.58260.60360.29910.082*
N10.15527 (8)0.98711 (13)0.13048 (7)0.0419 (3)
N20.19669 (8)0.88568 (13)0.17276 (8)0.0436 (3)
C10.01929 (10)1.09152 (16)0.08195 (8)0.0409 (4)
C20.06764 (12)1.19810 (18)0.04586 (9)0.0493 (4)
C30.01833 (15)1.3000 (2)0.00834 (11)0.0668 (5)
H3A0.05011.3716−0.01520.080*
C4−0.07686 (16)1.2964 (2)0.00557 (11)0.0709 (6)
H4−0.10891.3653−0.02000.085*
C5−0.12534 (13)1.1922 (2)0.04022 (11)0.0663 (6)
H5−0.18981.19000.03800.080*
C6−0.07735 (11)1.0909 (2)0.07839 (9)0.0533 (4)
H6−0.11021.02070.10220.064*
C70.06694 (10)0.98419 (16)0.12381 (9)0.0423 (4)
H70.03310.91310.14580.051*
C80.28882 (10)0.89504 (16)0.18561 (8)0.0411 (4)
C90.32990 (9)0.78911 (16)0.23665 (9)0.0396 (4)
C100.42602 (10)0.77388 (16)0.23447 (9)0.0402 (4)
H100.46120.83020.20330.048*
C110.46926 (9)0.67575 (16)0.27832 (9)0.0407 (4)
C120.41777 (11)0.59119 (18)0.32492 (9)0.0474 (4)
H120.44680.52400.35380.057*
C130.32267 (11)0.6079 (2)0.32798 (10)0.0561 (5)
H130.28780.55190.35960.067*
C140.27860 (11)0.70631 (19)0.28484 (9)0.0517 (4)
H140.21460.71720.28800.062*
H20.1622 (12)0.8175 (16)0.1921 (11)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0516 (7)0.0702 (10)0.0815 (10)−0.0133 (6)0.0067 (6)0.0162 (7)
O20.0375 (6)0.0518 (7)0.0680 (8)−0.0079 (5)−0.0066 (5)0.0050 (6)
O30.0286 (5)0.0524 (7)0.0835 (9)0.0054 (5)−0.0026 (5)0.0072 (6)
N10.0331 (6)0.0436 (8)0.0488 (7)0.0030 (5)−0.0044 (5)−0.0028 (6)
N20.0297 (6)0.0423 (8)0.0586 (8)0.0007 (5)−0.0060 (6)0.0025 (6)
C10.0378 (8)0.0462 (9)0.0387 (8)0.0039 (7)−0.0007 (6)−0.0018 (7)
C20.0507 (10)0.0523 (10)0.0448 (9)−0.0009 (8)0.0011 (7)−0.0004 (8)
C30.0846 (15)0.0592 (12)0.0566 (11)0.0036 (10)0.0013 (10)0.0144 (9)
C40.0794 (14)0.0749 (14)0.0583 (12)0.0259 (11)−0.0111 (11)0.0105 (10)
C50.0491 (10)0.0885 (15)0.0614 (12)0.0206 (10)−0.0073 (9)0.0031 (11)
C60.0401 (9)0.0672 (12)0.0525 (10)0.0064 (8)−0.0014 (7)0.0054 (9)
C70.0359 (8)0.0434 (9)0.0476 (9)−0.0005 (6)0.0000 (7)0.0001 (7)
C80.0312 (7)0.0424 (9)0.0497 (9)−0.0003 (7)−0.0027 (6)−0.0081 (7)
C90.0286 (7)0.0440 (9)0.0461 (8)−0.0005 (6)−0.0040 (6)−0.0075 (7)
C100.0296 (7)0.0395 (8)0.0516 (9)−0.0022 (6)0.0002 (6)−0.0050 (7)
C110.0275 (7)0.0417 (8)0.0529 (9)0.0026 (6)−0.0050 (7)−0.0113 (7)
C120.0414 (8)0.0540 (10)0.0467 (9)0.0054 (7)−0.0046 (7)0.0004 (8)
C130.0394 (9)0.0740 (13)0.0548 (10)−0.0012 (8)0.0048 (7)0.0130 (9)
C140.0282 (7)0.0729 (12)0.0541 (10)0.0016 (7)0.0006 (7)0.0026 (9)

Geometric parameters (Å, °)

O1—C21.356 (2)C4—H40.9300
O1—H10.8200C5—C61.380 (3)
O2—C81.2360 (18)C5—H50.9300
O3—C111.3673 (17)C6—H60.9300
O3—H30.8200C7—H70.9300
N1—C71.2784 (18)C8—C91.494 (2)
N1—N21.3745 (18)C9—C141.389 (2)
N2—C81.3499 (18)C9—C101.3928 (19)
N2—H20.895 (9)C10—C111.379 (2)
C1—C61.394 (2)C10—H100.9300
C1—C21.401 (2)C11—C121.383 (2)
C1—C71.452 (2)C12—C131.380 (2)
C2—C31.388 (2)C12—H120.9300
C3—C41.373 (3)C13—C141.380 (2)
C3—H3A0.9300C13—H130.9300
C4—C51.373 (3)C14—H140.9300
C2—O1—H1109.5N1—C7—C1120.20 (14)
C11—O3—H3109.5N1—C7—H7119.9
C7—N1—N2117.88 (13)C1—C7—H7119.9
C8—N2—N1118.21 (13)O2—C8—N2121.25 (14)
C8—N2—H2122.0 (13)O2—C8—C9122.15 (13)
N1—N2—H2119.8 (13)N2—C8—C9116.60 (13)
C6—C1—C2118.60 (15)C14—C9—C10119.03 (14)
C6—C1—C7119.53 (15)C14—C9—C8124.29 (13)
C2—C1—C7121.86 (14)C10—C9—C8116.68 (13)
O1—C2—C3118.19 (16)C11—C10—C9120.37 (14)
O1—C2—C1122.45 (15)C11—C10—H10119.8
C3—C2—C1119.36 (17)C9—C10—H10119.8
C4—C3—C2120.71 (19)O3—C11—C10116.77 (14)
C4—C3—H3A119.6O3—C11—C12122.77 (14)
C2—C3—H3A119.6C10—C11—C12120.46 (13)
C3—C4—C5120.68 (18)C13—C12—C11119.15 (15)
C3—C4—H4119.7C13—C12—H12120.4
C5—C4—H4119.7C11—C12—H12120.4
C4—C5—C6119.29 (18)C14—C13—C12120.98 (16)
C4—C5—H5120.4C14—C13—H13119.5
C6—C5—H5120.4C12—C13—H13119.5
C5—C6—C1121.34 (18)C13—C14—C9119.98 (14)
C5—C6—H6119.3C13—C14—H14120.0
C1—C6—H6119.3C9—C14—H14120.0

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.882.6010 (19)146.
O3—H3···O2i0.821.812.5946 (16)159.
N2—H2···O3ii0.90 (1)2.12 (1)3.0062 (18)171.(2)

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x−1/2, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2164).

References

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