Acta Cryst. (2008). E64, o1864 [ doi:10.1107/S1600536808027426 ]
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-HO and N-HO hydrogen bonds into a two-dimensional polymeric structure parallel to the ab plane.
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.
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).
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./gk2164fig1thm.gif)
| 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. |
![[Figure 2]](./gk2164fig2thm.gif)
| Fig. 2. Packing diagram, viewed along the a axis. Hydrogen bonds are shown as dashed lines. |
| C14H12N2O3 | F(000) = 1072 |
| Mr = 256.26 | Dx = 1.366 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 3092 reflections |
| a = 14.405 (2) Å | θ = 2.7–26.0° |
| b = 9.661 (1) Å | µ = 0.10 mm−1 |
| c = 17.905 (2) Å | T = 298 K |
| V = 2491.8 (5) Å3 | Block, colorless |
| Z = 8 | 0.23 × 0.20 × 0.20 mm |
| Bruker SMART 1000 CCD area-detector diffractometer | 2720 independent reflections |
| Radiation source: fine-focus sealed tube | 1869 reflections with I > 2σ(I) |
| graphite | Rint = 0.039 |
| ω scans | θmax = 27.0°, θmin = 2.3° |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −15→18 |
| Tmin = 0.978, Tmax = 0.981 | k = −11→12 |
| 13415 measured reflections | l = −22→22 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0535P)2 + 0.3997P] where P = (Fo2 + 2Fc2)/3 |
| 2720 reflections | (Δ/σ)max < 0.001 |
| 177 parameters | Δρmax = 0.13 e Å−3 |
| 1 restraint | Δρmin = −0.18 e Å−3 |
| C14H12N2O3 | V = 2491.8 (5) Å3 |
| Mr = 256.26 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 14.405 (2) Å | µ = 0.10 mm−1 |
| b = 9.661 (1) Å | T = 298 K |
| c = 17.905 (2) Å | 0.23 × 0.20 × 0.20 mm |
| Bruker SMART 1000 CCD area-detector diffractometer | 2720 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1869 reflections with I > 2σ(I) |
| Tmin = 0.978, Tmax = 0.981 | Rint = 0.039 |
| 13415 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.119 | Δρmax = 0.13 e Å−3 |
| S = 1.03 | Δρmin = −0.18 e Å−3 |
| 2720 reflections | Absolute structure: ? |
| 177 parameters | Flack parameter: ? |
| 1 restraint | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.16163 (8) | 1.20579 (14) | 0.04590 (8) | 0.0677 (4) | |
| H1 | 0.1829 | 1.1427 | 0.0713 | 0.102* | |
| O2 | 0.33625 (7) | 0.98665 (12) | 0.15618 (6) | 0.0524 (3) | |
| O3 | 0.56381 (7) | 0.66767 (12) | 0.27314 (7) | 0.0548 (3) | |
| H3 | 0.5826 | 0.6036 | 0.2991 | 0.082* | |
| N1 | 0.15527 (8) | 0.98711 (13) | 0.13048 (7) | 0.0419 (3) | |
| N2 | 0.19669 (8) | 0.88568 (13) | 0.17276 (8) | 0.0436 (3) | |
| C1 | 0.01929 (10) | 1.09152 (16) | 0.08195 (8) | 0.0409 (4) | |
| C2 | 0.06764 (12) | 1.19810 (18) | 0.04586 (9) | 0.0493 (4) | |
| C3 | 0.01833 (15) | 1.3000 (2) | 0.00834 (11) | 0.0668 (5) | |
| H3A | 0.0501 | 1.3716 | −0.0152 | 0.080* | |
| C4 | −0.07686 (16) | 1.2964 (2) | 0.00557 (11) | 0.0709 (6) | |
| H4 | −0.1089 | 1.3653 | −0.0200 | 0.085* | |
| C5 | −0.12534 (13) | 1.1922 (2) | 0.04022 (11) | 0.0663 (6) | |
| H5 | −0.1898 | 1.1900 | 0.0380 | 0.080* | |
| C6 | −0.07735 (11) | 1.0909 (2) | 0.07839 (9) | 0.0533 (4) | |
| H6 | −0.1102 | 1.0207 | 0.1022 | 0.064* | |
| C7 | 0.06694 (10) | 0.98419 (16) | 0.12381 (9) | 0.0423 (4) | |
| H7 | 0.0331 | 0.9131 | 0.1458 | 0.051* | |
| C8 | 0.28882 (10) | 0.89504 (16) | 0.18561 (8) | 0.0411 (4) | |
| C9 | 0.32990 (9) | 0.78911 (16) | 0.23665 (9) | 0.0396 (4) | |
| C10 | 0.42602 (10) | 0.77388 (16) | 0.23447 (9) | 0.0402 (4) | |
| H10 | 0.4612 | 0.8302 | 0.2033 | 0.048* | |
| C11 | 0.46926 (9) | 0.67575 (16) | 0.27832 (9) | 0.0407 (4) | |
| C12 | 0.41777 (11) | 0.59119 (18) | 0.32492 (9) | 0.0474 (4) | |
| H12 | 0.4468 | 0.5240 | 0.3538 | 0.057* | |
| C13 | 0.32267 (11) | 0.6079 (2) | 0.32798 (10) | 0.0561 (5) | |
| H13 | 0.2878 | 0.5519 | 0.3596 | 0.067* | |
| C14 | 0.27860 (11) | 0.70631 (19) | 0.28484 (9) | 0.0517 (4) | |
| H14 | 0.2146 | 0.7172 | 0.2880 | 0.062* | |
| H2 | 0.1622 (12) | 0.8175 (16) | 0.1921 (11) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0516 (7) | 0.0702 (10) | 0.0815 (10) | −0.0133 (6) | 0.0067 (6) | 0.0162 (7) |
| O2 | 0.0375 (6) | 0.0518 (7) | 0.0680 (8) | −0.0079 (5) | −0.0066 (5) | 0.0050 (6) |
| O3 | 0.0286 (5) | 0.0524 (7) | 0.0835 (9) | 0.0054 (5) | −0.0026 (5) | 0.0072 (6) |
| N1 | 0.0331 (6) | 0.0436 (8) | 0.0488 (7) | 0.0030 (5) | −0.0044 (5) | −0.0028 (6) |
| N2 | 0.0297 (6) | 0.0423 (8) | 0.0586 (8) | 0.0007 (5) | −0.0060 (6) | 0.0025 (6) |
| C1 | 0.0378 (8) | 0.0462 (9) | 0.0387 (8) | 0.0039 (7) | −0.0007 (6) | −0.0018 (7) |
| C2 | 0.0507 (10) | 0.0523 (10) | 0.0448 (9) | −0.0009 (8) | 0.0011 (7) | −0.0004 (8) |
| C3 | 0.0846 (15) | 0.0592 (12) | 0.0566 (11) | 0.0036 (10) | 0.0013 (10) | 0.0144 (9) |
| C4 | 0.0794 (14) | 0.0749 (14) | 0.0583 (12) | 0.0259 (11) | −0.0111 (11) | 0.0105 (10) |
| C5 | 0.0491 (10) | 0.0885 (15) | 0.0614 (12) | 0.0206 (10) | −0.0073 (9) | 0.0031 (11) |
| C6 | 0.0401 (9) | 0.0672 (12) | 0.0525 (10) | 0.0064 (8) | −0.0014 (7) | 0.0054 (9) |
| C7 | 0.0359 (8) | 0.0434 (9) | 0.0476 (9) | −0.0005 (6) | 0.0000 (7) | 0.0001 (7) |
| C8 | 0.0312 (7) | 0.0424 (9) | 0.0497 (9) | −0.0003 (7) | −0.0027 (6) | −0.0081 (7) |
| C9 | 0.0286 (7) | 0.0440 (9) | 0.0461 (8) | −0.0005 (6) | −0.0040 (6) | −0.0075 (7) |
| C10 | 0.0296 (7) | 0.0395 (8) | 0.0516 (9) | −0.0022 (6) | 0.0002 (6) | −0.0050 (7) |
| C11 | 0.0275 (7) | 0.0417 (8) | 0.0529 (9) | 0.0026 (6) | −0.0050 (7) | −0.0113 (7) |
| C12 | 0.0414 (8) | 0.0540 (10) | 0.0467 (9) | 0.0054 (7) | −0.0046 (7) | 0.0004 (8) |
| C13 | 0.0394 (9) | 0.0740 (13) | 0.0548 (10) | −0.0012 (8) | 0.0048 (7) | 0.0130 (9) |
| C14 | 0.0282 (7) | 0.0729 (12) | 0.0541 (10) | 0.0016 (7) | 0.0006 (7) | 0.0026 (9) |
| O1—C2 | 1.356 (2) | C4—H4 | 0.9300 |
| O1—H1 | 0.8200 | C5—C6 | 1.380 (3) |
| O2—C8 | 1.2360 (18) | C5—H5 | 0.9300 |
| O3—C11 | 1.3673 (17) | C6—H6 | 0.9300 |
| O3—H3 | 0.8200 | C7—H7 | 0.9300 |
| N1—C7 | 1.2784 (18) | C8—C9 | 1.494 (2) |
| N1—N2 | 1.3745 (18) | C9—C14 | 1.389 (2) |
| N2—C8 | 1.3499 (18) | C9—C10 | 1.3928 (19) |
| N2—H2 | 0.895 (9) | C10—C11 | 1.379 (2) |
| C1—C6 | 1.394 (2) | C10—H10 | 0.9300 |
| C1—C2 | 1.401 (2) | C11—C12 | 1.383 (2) |
| C1—C7 | 1.452 (2) | C12—C13 | 1.380 (2) |
| C2—C3 | 1.388 (2) | C12—H12 | 0.9300 |
| C3—C4 | 1.373 (3) | C13—C14 | 1.380 (2) |
| C3—H3A | 0.9300 | C13—H13 | 0.9300 |
| C4—C5 | 1.373 (3) | C14—H14 | 0.9300 |
| C2—O1—H1 | 109.5 | N1—C7—C1 | 120.20 (14) |
| C11—O3—H3 | 109.5 | N1—C7—H7 | 119.9 |
| C7—N1—N2 | 117.88 (13) | C1—C7—H7 | 119.9 |
| C8—N2—N1 | 118.21 (13) | O2—C8—N2 | 121.25 (14) |
| C8—N2—H2 | 122.0 (13) | O2—C8—C9 | 122.15 (13) |
| N1—N2—H2 | 119.8 (13) | N2—C8—C9 | 116.60 (13) |
| C6—C1—C2 | 118.60 (15) | C14—C9—C10 | 119.03 (14) |
| C6—C1—C7 | 119.53 (15) | C14—C9—C8 | 124.29 (13) |
| C2—C1—C7 | 121.86 (14) | C10—C9—C8 | 116.68 (13) |
| O1—C2—C3 | 118.19 (16) | C11—C10—C9 | 120.37 (14) |
| O1—C2—C1 | 122.45 (15) | C11—C10—H10 | 119.8 |
| C3—C2—C1 | 119.36 (17) | C9—C10—H10 | 119.8 |
| C4—C3—C2 | 120.71 (19) | O3—C11—C10 | 116.77 (14) |
| C4—C3—H3A | 119.6 | O3—C11—C12 | 122.77 (14) |
| C2—C3—H3A | 119.6 | C10—C11—C12 | 120.46 (13) |
| C3—C4—C5 | 120.68 (18) | C13—C12—C11 | 119.15 (15) |
| C3—C4—H4 | 119.7 | C13—C12—H12 | 120.4 |
| C5—C4—H4 | 119.7 | C11—C12—H12 | 120.4 |
| C4—C5—C6 | 119.29 (18) | C14—C13—C12 | 120.98 (16) |
| C4—C5—H5 | 120.4 | C14—C13—H13 | 119.5 |
| C6—C5—H5 | 120.4 | C12—C13—H13 | 119.5 |
| C5—C6—C1 | 121.34 (18) | C13—C14—C9 | 119.98 (14) |
| C5—C6—H6 | 119.3 | C13—C14—H14 | 120.0 |
| C1—C6—H6 | 119.3 | C9—C14—H14 | 120.0 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.82 | 1.88 | 2.6010 (19) | 146. |
| O3—H3···O2i | 0.82 | 1.81 | 2.5946 (16) | 159. |
| N2—H2···O3ii | 0.90 (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. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.82 | 1.88 | 2.6010 (19) | 146. |
| O3—H3···O2i | 0.82 | 1.81 | 2.5946 (16) | 159. |
| N2—H2···O3ii | 0.90 (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. |
We acknowledge Changsha University of Science and Technology for research grants.
Ali, H. M., Kamalul Aripin, N. F. & Ng, S. W. (2005). Acta Cryst. E61, m433–m434.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Eltayeb, N. E., Teoh, S. G., Chantrapromma, S., Fun, H.-K. & Adnan, R. (2008). Acta Cryst. E64, m912–m913.
Habibi, M. H., Montazerozohori, M., Lalegani, A., Mokhtari, R., Harrington, R. W. & Clegg, W. (2007). Acta Cryst. E63, m2933–m2934.
Jing, Z.-L., Zhao, Y.-L., Chen, X. & Yu, M. (2006). Acta Cryst. E62, o4087–o4088.
Ling, C.-H., Chen, Y.-B., Huang, J.-A., Ji, C. & Liu, P. (2008). Acta Cryst. E64, o948.
Peng, S.-J., Ping, W.-J. & Song, L.-B. (2007). Z. Kristallogr. New Cryst. Struct. 222, 425–426.
Peng, S.-J., Yang, T. & Zhou, C.-S. (2006). Acta Cryst. E62, m235–m236.
Peng, S.-J. & You, Z.-L. (2007). J. Chem. Crystallogr. 37, 415–419.
Peng, S.-J. & Zhou, C.-S. (2007). Acta Cryst. E63, m3185.
Peng, S.-J., Zhou, C.-S. & Yang, T. (2006). Acta Cryst. E62, m1147–m1149.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Yehye, W. A., Ariffin, A. & Ng, S. W. (2008a). Acta Cryst. E64, o960.
Yehye, W. A., Ariffin, A. & Ng, S. W. (2008b). Acta Cryst. E64, o1452.
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).