Acta Cryst. (2008). E64, o2026 [ doi:10.1107/S1600536808030729 ]
Crystals of the title compound, C10H8N2O2, were obtained from a condensation reaction of hydrazine hydrate with furfural. In the crystal structure, the molecule is centrosymmetric and almost planar and the furan rings are parallel by symmetry.
Hydrazine hydrate (35% solution in water, 0.71 g, 5 mmol) and furfural (0.96 g, 10 mmol) were mixed, at the same time adding 2 or 3 drops of formic acid, and stirred at room temperature in 30 ml of ethanol solution for 2 days, and then the filtrate was kept open to slowly evaporate for a few days, depositing yellow blocks of (I).
The H atoms attached were placed in geometrically idealized positions (C—H = 0.93 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).
![[Figure 1]](./hb2802fig1thm.gif)
| Fig. 1. A view of the molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level (arbitrary spheres for the H atoms). The unlabelled atoms are generated by the symmetry operation (1-x, 2-y, -z). |
| C10H8N2O2 | F(000) = 392 |
| Mr = 188.18 | Dx = 1.332 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 5207 reflections |
| a = 6.877 (2) Å | θ = 2.6–25.3° |
| b = 8.996 (3) Å | µ = 0.10 mm−1 |
| c = 15.171 (4) Å | T = 298 K |
| V = 938.6 (5) Å3 | Block, yellow |
| Z = 4 | 0.50 × 0.40 × 0.40 mm |
| Bruker SMART 1K CCD diffractometer | 829 independent reflections |
| Radiation source: fine-focus sealed tube | 677 reflections with I > 2σ(I) |
| graphite | Rint = 0.081 |
| ω scans | θmax = 25.3°, θmin = 2.6° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −8→8 |
| Tmin = 0.954, Tmax = 0.963 | k = −10→10 |
| 4129 measured reflections | l = −18→9 |
| 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.105 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0662P)2] where P = (Fo2 + 2Fc2)/3 |
| 829 reflections | (Δ/σ)max < 0.001 |
| 65 parameters | Δρmax = 0.16 e Å−3 |
| 0 restraints | Δρmin = −0.25 e Å−3 |
| C10H8N2O2 | V = 938.6 (5) Å3 |
| Mr = 188.18 | Z = 4 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 6.877 (2) Å | µ = 0.10 mm−1 |
| b = 8.996 (3) Å | T = 298 K |
| c = 15.171 (4) Å | 0.50 × 0.40 × 0.40 mm |
| Bruker SMART 1K CCD diffractometer | 829 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 677 reflections with I > 2σ(I) |
| Tmin = 0.954, Tmax = 0.963 | Rint = 0.081 |
| 4129 measured reflections | θmax = 25.3° |
| R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
| wR(F2) = 0.105 | Δρmax = 0.16 e Å−3 |
| S = 1.05 | Δρmin = −0.25 e Å−3 |
| 829 reflections | Absolute structure: ? |
| 65 parameters | Flack parameter: ? |
| 0 restraints | 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 | ||
| C1 | −0.0467 (2) | 0.88870 (18) | 0.18436 (11) | 0.0736 (5) | |
| H1 | −0.0937 | 0.8074 | 0.2157 | 0.088* | |
| C2 | −0.1336 (2) | 1.01970 (19) | 0.18094 (10) | 0.0719 (5) | |
| H2 | −0.2492 | 1.0466 | 0.2084 | 0.086* | |
| C3 | −0.0168 (2) | 1.10963 (17) | 0.12769 (10) | 0.0642 (5) | |
| H3 | −0.0400 | 1.2085 | 0.1131 | 0.077* | |
| C4 | 0.13456 (19) | 1.02755 (14) | 0.10149 (8) | 0.0529 (4) | |
| C5 | 0.2964 (2) | 1.06191 (15) | 0.04628 (9) | 0.0566 (4) | |
| H5 | 0.3049 | 1.1570 | 0.0225 | 0.068* | |
| N1 | 0.42950 (18) | 0.96866 (13) | 0.02805 (8) | 0.0613 (4) | |
| O1 | 0.12017 (16) | 0.88799 (10) | 0.13632 (7) | 0.0669 (4) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0695 (10) | 0.0698 (11) | 0.0815 (11) | −0.0135 (8) | 0.0114 (9) | 0.0137 (8) |
| C2 | 0.0637 (10) | 0.0800 (12) | 0.0721 (11) | 0.0049 (8) | 0.0084 (7) | 0.0085 (8) |
| C3 | 0.0722 (11) | 0.0589 (10) | 0.0616 (9) | 0.0093 (7) | 0.0038 (7) | 0.0082 (7) |
| C4 | 0.0639 (9) | 0.0452 (8) | 0.0496 (7) | −0.0049 (6) | −0.0044 (6) | 0.0007 (6) |
| C5 | 0.0690 (10) | 0.0485 (8) | 0.0522 (8) | −0.0055 (7) | 0.0007 (7) | 0.0013 (6) |
| N1 | 0.0649 (8) | 0.0541 (8) | 0.0649 (8) | −0.0033 (6) | 0.0084 (5) | 0.0045 (5) |
| O1 | 0.0698 (8) | 0.0479 (7) | 0.0830 (8) | −0.0029 (5) | 0.0078 (5) | 0.0057 (4) |
| C1—C2 | 1.322 (2) | C3—H3 | 0.9300 |
| C1—O1 | 1.359 (2) | C4—O1 | 1.3657 (16) |
| C1—H1 | 0.9300 | C4—C5 | 1.427 (2) |
| C2—C3 | 1.397 (2) | C5—N1 | 1.2721 (18) |
| C2—H2 | 0.9300 | C5—H5 | 0.9300 |
| C3—C4 | 1.3364 (19) | N1—N1i | 1.408 (2) |
| C2—C1—O1 | 111.39 (14) | C3—C4—O1 | 109.66 (12) |
| C2—C1—H1 | 124.3 | C3—C4—C5 | 131.47 (13) |
| O1—C1—H1 | 124.3 | O1—C4—C5 | 118.87 (12) |
| C1—C2—C3 | 106.18 (15) | N1—C5—C4 | 123.10 (13) |
| C1—C2—H2 | 126.9 | N1—C5—H5 | 118.4 |
| C3—C2—H2 | 126.9 | C4—C5—H5 | 118.4 |
| C4—C3—C2 | 107.45 (14) | C5—N1—N1i | 111.29 (15) |
| C4—C3—H3 | 126.3 | C1—O1—C4 | 105.32 (12) |
| C2—C3—H3 | 126.3 | ||
| O1—C1—C2—C3 | −0.05 (19) | O1—C4—C5—N1 | −0.4 (2) |
| C1—C2—C3—C4 | 0.23 (18) | C4—C5—N1—N1i | 179.64 (14) |
| C2—C3—C4—O1 | −0.32 (17) | C2—C1—O1—C4 | −0.14 (18) |
| C2—C3—C4—C5 | 179.42 (15) | C3—C4—O1—C1 | 0.29 (16) |
| C3—C4—C5—N1 | 179.91 (15) | C5—C4—O1—C1 | −179.49 (12) |
| Symmetry codes: (i) −x+1, −y+2, −z. |
The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 20471033), the Natural Science Foundation of Shanxi Province of China (grant No. 20051013) and the Overseas Returned Scholar Foundation of Shanxi Province of China in 2006.
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Casellato, U. & Vigato, P. A. (1977). Coord. Chem. Rev. 23, 31–50.
Fan, Z., Shan, S., Wang, S.-H. & Wang, W.-L. (2008). Acta Cryst. E64, o1341.
Shan, S., Fan, Z., Hu, W.-X. & Xu, D.-J. (2004). Acta Cryst. E60, o2473–o2475.
Shan, S., Tian, Y.-L., Wang, S.-H., Wang, W.-L. & Xu, Y.-L. (2008). Acta Cryst. E64, o1153.
Shan, S., Wang, W.-L., Xie, P.-J., Xu, Y.-L. & Wang, S.-H. (2008). Acta Cryst. E64, o1386.
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Schiff bases have been studied for decades (Casellato & Vigato 1977) and they are still one of the most prevalent mixed-donor ligands in coordination chemistry, with numerous applications including single-molecule magnetism, materials science and catalysis. Here, the synthsis and crystal structure of the title compound (I) are reported.
The molecule of (I) is centrosymmetric, with the midpoint of the N—N bond located on the inversion center. The C5—N1 double bond distance of 1.272 (2) Å is shorter than the C═N bond distance found in related hydrazone structures, i.e. 1.295 (2) Å in (E)-3-methoxyacetophenone 4-nitrophenylhydrazone (Fan et al., 2008), 1.298 (2) Å in (E)-2-furylmethylketone 2,4-dinitrophenylhydrazone (Shan, Tian et al., 2008) and 1.293 (2) Å in benzylideneacetone 2,4-dinitrophenylhydrazone (Shan et al., 2004). It is indistinguishable from the length of 1.273 (1) Å in 2-methylbenzaldehyde 2-methylbenzylidenehydrazone (Shan, Wang et al., 2008).