Acta Cryst. (2009). E65, o2301 [ doi:10.1107/S1600536809034242 ]
In the title compound, C16H16N2O4·H2O, the dihedral angle between the two aromatic rings is 19.6 (2)°. In the crystal structure, molecules are linked into a three-dimensional network by intermolecular N-H
O, O-HN and O-HO hydrogen bonds.
The title compound was prepared by the Schiff base condensation of 4-hydroxy-3-methoxybenzaldehyde (0.1 mol) and 4-methoxybenzohydrazide (0.1 mmol) in 95% ethanol (50 ml). The excess ethanol was removed by distillation. The colourless solid obtained was filtered and washed with ethanol. Colourless blokcs of (I) were obatined by slow evaporation of a 95% ethanol solution at room temperature.
The imino H atom and water H atoms were located in a difference map and refined with N—H, O—H, and H···H distance restraint of 0.90 (1), 0.85 (1), and 1.37 (2) Å, respectively. Other H atoms were positioned geometrically (C—H = 0.93-0.97 Å, O—H = 0.82 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl and O).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./hb5071fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids. |
![[Figure 2]](./hb5071fig2thm.gif)
| Fig. 2. The crystal packing of (I) viewed along the a axis. Intermolecular hydrogen bonds are drawn by dashed lines. H atoms unrelated to the hydrogen bonding are omitted for clarity. |
| C16H16N2O4·H2O | F(000) = 672 |
| Mr = 318.32 | Dx = 1.274 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 2203 reflections |
| a = 7.942 (1) Å | θ = 2.3–24.6° |
| b = 21.273 (2) Å | µ = 0.10 mm−1 |
| c = 10.246 (1) Å | T = 298 K |
| β = 106.596 (2)° | Block, colourless |
| V = 1659.0 (3) Å3 | 0.32 × 0.30 × 0.30 mm |
| Z = 4 |
| Bruker APEXII CCD diffractometer | 3338 independent reflections |
| Radiation source: fine-focus sealed tube | 2291 reflections with I > 2σ(I) |
| graphite | Rint = 0.024 |
| ω scans | θmax = 26.3°, θmin = 1.9° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −9→9 |
| Tmin = 0.970, Tmax = 0.972 | k = −26→25 |
| 9533 measured reflections | l = −12→11 |
| 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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.04 | w = 1/[σ2(Fo2) + (0.0586P)2 + 0.2417P] where P = (Fo2 + 2Fc2)/3 |
| 3338 reflections | (Δ/σ)max = 0.001 |
| 220 parameters | Δρmax = 0.20 e Å−3 |
| 4 restraints | Δρmin = −0.18 e Å−3 |
| C16H16N2O4·H2O | V = 1659.0 (3) Å3 |
| Mr = 318.32 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 7.942 (1) Å | µ = 0.10 mm−1 |
| b = 21.273 (2) Å | T = 298 K |
| c = 10.246 (1) Å | 0.32 × 0.30 × 0.30 mm |
| β = 106.596 (2)° |
| Bruker APEXII CCD diffractometer | 3338 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 2291 reflections with I > 2σ(I) |
| Tmin = 0.970, Tmax = 0.972 | Rint = 0.024 |
| 9533 measured reflections | θmax = 26.3° |
| R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.127 | Δρmax = 0.20 e Å−3 |
| S = 1.04 | Δρmin = −0.18 e Å−3 |
| 3338 reflections | Absolute structure: ? |
| 220 parameters | Flack parameter: ? |
| 4 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.45414 (18) | 0.25435 (6) | −0.34503 (15) | 0.0726 (4) | |
| O2 | 0.25510 (15) | 0.15740 (6) | −0.42933 (13) | 0.0570 (3) | |
| H2 | 0.1742 | 0.1332 | −0.4638 | 0.085* | |
| O3 | 0.32814 (18) | 0.47213 (6) | 0.11553 (15) | 0.0682 (4) | |
| O4 | −0.1311 (2) | 0.60007 (7) | 0.46039 (15) | 0.0791 (4) | |
| O5 | 0.01680 (17) | 0.08043 (6) | 0.43784 (15) | 0.0612 (4) | |
| N1 | 0.16872 (18) | 0.37019 (6) | −0.01397 (14) | 0.0489 (4) | |
| N2 | 0.10078 (19) | 0.40488 (7) | 0.07401 (15) | 0.0508 (4) | |
| C1 | 0.1256 (2) | 0.28010 (8) | −0.15935 (17) | 0.0477 (4) | |
| C2 | 0.2726 (2) | 0.29018 (8) | −0.20479 (17) | 0.0487 (4) | |
| H2A | 0.3435 | 0.3251 | −0.1744 | 0.058* | |
| C3 | 0.3135 (2) | 0.24897 (8) | −0.29416 (17) | 0.0475 (4) | |
| C4 | 0.2067 (2) | 0.19639 (8) | −0.34092 (17) | 0.0456 (4) | |
| C5 | 0.0626 (2) | 0.18616 (9) | −0.29573 (19) | 0.0562 (5) | |
| H5 | −0.0079 | 0.1511 | −0.3256 | 0.067* | |
| C6 | 0.0218 (2) | 0.22785 (9) | −0.2059 (2) | 0.0600 (5) | |
| H6 | −0.0768 | 0.2207 | −0.1762 | 0.072* | |
| C7 | 0.5593 (3) | 0.30919 (11) | −0.3109 (3) | 0.0894 (8) | |
| H7A | 0.4872 | 0.3458 | −0.3389 | 0.134* | |
| H7B | 0.6494 | 0.3084 | −0.3565 | 0.134* | |
| H7C | 0.6125 | 0.3105 | −0.2142 | 0.134* | |
| C8 | 0.0764 (2) | 0.32266 (8) | −0.06566 (18) | 0.0512 (4) | |
| H8 | −0.0267 | 0.3149 | −0.0425 | 0.061* | |
| C9 | 0.1854 (2) | 0.45679 (8) | 0.13293 (18) | 0.0507 (4) | |
| C10 | 0.1005 (2) | 0.49380 (8) | 0.21918 (18) | 0.0510 (4) | |
| C11 | 0.1991 (3) | 0.53788 (10) | 0.3066 (2) | 0.0729 (6) | |
| H11 | 0.3163 | 0.5435 | 0.3099 | 0.087* | |
| C12 | 0.1273 (3) | 0.57418 (10) | 0.3899 (2) | 0.0757 (6) | |
| H12 | 0.1966 | 0.6033 | 0.4491 | 0.091* | |
| C13 | −0.0457 (3) | 0.56687 (9) | 0.38450 (19) | 0.0602 (5) | |
| C14 | −0.1466 (3) | 0.52298 (9) | 0.2976 (2) | 0.0623 (5) | |
| H14 | −0.2638 | 0.5174 | 0.2945 | 0.075* | |
| C15 | −0.0741 (3) | 0.48746 (8) | 0.21579 (19) | 0.0568 (5) | |
| H15 | −0.1440 | 0.4584 | 0.1566 | 0.068* | |
| C16 | −0.0366 (4) | 0.64796 (11) | 0.5474 (2) | 0.0959 (8) | |
| H16A | 0.0642 | 0.6299 | 0.6119 | 0.144* | |
| H16B | −0.1111 | 0.6672 | 0.5951 | 0.144* | |
| H16C | 0.0012 | 0.6791 | 0.4941 | 0.144* | |
| H2B | 0.0004 (18) | 0.3933 (10) | 0.090 (2) | 0.080* | |
| H5B | 0.064 (2) | 0.0464 (7) | 0.421 (2) | 0.080* | |
| H5A | −0.064 (2) | 0.0719 (9) | 0.473 (2) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0662 (8) | 0.0727 (9) | 0.0998 (10) | −0.0254 (7) | 0.0572 (8) | −0.0298 (8) |
| O2 | 0.0520 (7) | 0.0565 (7) | 0.0720 (8) | −0.0056 (6) | 0.0329 (7) | −0.0161 (6) |
| O3 | 0.0697 (9) | 0.0606 (8) | 0.0880 (10) | −0.0194 (7) | 0.0443 (8) | −0.0096 (7) |
| O4 | 0.1010 (11) | 0.0712 (9) | 0.0694 (9) | 0.0105 (8) | 0.0311 (8) | −0.0178 (8) |
| O5 | 0.0558 (8) | 0.0502 (7) | 0.0862 (10) | −0.0013 (6) | 0.0342 (7) | −0.0118 (7) |
| N1 | 0.0522 (8) | 0.0479 (8) | 0.0549 (8) | −0.0001 (7) | 0.0285 (7) | −0.0016 (7) |
| N2 | 0.0560 (9) | 0.0487 (8) | 0.0582 (9) | −0.0065 (7) | 0.0329 (7) | −0.0072 (7) |
| C1 | 0.0480 (9) | 0.0491 (9) | 0.0524 (10) | −0.0014 (7) | 0.0249 (8) | −0.0019 (8) |
| C2 | 0.0498 (10) | 0.0460 (9) | 0.0557 (10) | −0.0071 (8) | 0.0241 (8) | −0.0036 (8) |
| C3 | 0.0423 (9) | 0.0515 (9) | 0.0561 (10) | −0.0040 (7) | 0.0259 (8) | −0.0023 (8) |
| C4 | 0.0455 (9) | 0.0455 (9) | 0.0509 (10) | 0.0010 (7) | 0.0219 (8) | −0.0026 (7) |
| C5 | 0.0515 (10) | 0.0550 (10) | 0.0704 (12) | −0.0125 (8) | 0.0307 (9) | −0.0129 (9) |
| C6 | 0.0529 (11) | 0.0630 (11) | 0.0772 (13) | −0.0131 (9) | 0.0397 (10) | −0.0128 (10) |
| C7 | 0.0736 (14) | 0.0922 (16) | 0.125 (2) | −0.0380 (13) | 0.0656 (15) | −0.0365 (15) |
| C8 | 0.0509 (10) | 0.0531 (10) | 0.0587 (11) | −0.0051 (8) | 0.0304 (8) | −0.0027 (8) |
| C9 | 0.0588 (11) | 0.0451 (9) | 0.0536 (10) | −0.0068 (8) | 0.0247 (8) | 0.0040 (8) |
| C10 | 0.0649 (11) | 0.0415 (9) | 0.0511 (10) | −0.0042 (8) | 0.0238 (9) | 0.0016 (8) |
| C11 | 0.0790 (14) | 0.0676 (13) | 0.0817 (14) | −0.0244 (11) | 0.0383 (12) | −0.0179 (11) |
| C12 | 0.0937 (17) | 0.0644 (13) | 0.0748 (14) | −0.0245 (12) | 0.0335 (12) | −0.0234 (11) |
| C13 | 0.0831 (14) | 0.0490 (10) | 0.0522 (11) | 0.0069 (10) | 0.0252 (10) | −0.0008 (8) |
| C14 | 0.0600 (12) | 0.0637 (12) | 0.0634 (12) | 0.0082 (9) | 0.0179 (10) | −0.0075 (10) |
| C15 | 0.0593 (11) | 0.0528 (10) | 0.0574 (11) | 0.0019 (8) | 0.0151 (9) | −0.0089 (9) |
| C16 | 0.136 (2) | 0.0756 (14) | 0.0731 (15) | 0.0114 (15) | 0.0258 (15) | −0.0260 (13) |
| O1—C3 | 1.3654 (19) | C5—H5 | 0.9300 |
| O1—C7 | 1.419 (2) | C6—H6 | 0.9300 |
| O2—C4 | 1.3622 (19) | C7—H7A | 0.9600 |
| O2—H2 | 0.8200 | C7—H7B | 0.9600 |
| O3—C9 | 1.241 (2) | C7—H7C | 0.9600 |
| O4—C13 | 1.365 (2) | C8—H8 | 0.9300 |
| O4—C16 | 1.419 (3) | C9—C10 | 1.482 (2) |
| O5—H5B | 0.856 (9) | C10—C11 | 1.376 (3) |
| O5—H5A | 0.846 (9) | C10—C15 | 1.384 (3) |
| N1—C8 | 1.272 (2) | C11—C12 | 1.388 (3) |
| N1—N2 | 1.3878 (18) | C11—H11 | 0.9300 |
| N2—C9 | 1.343 (2) | C12—C13 | 1.369 (3) |
| N2—H2B | 0.895 (9) | C12—H12 | 0.9300 |
| C1—C6 | 1.385 (2) | C13—C14 | 1.378 (3) |
| C1—C2 | 1.391 (2) | C14—C15 | 1.372 (2) |
| C1—C8 | 1.452 (2) | C14—H14 | 0.9300 |
| C2—C3 | 1.372 (2) | C15—H15 | 0.9300 |
| C2—H2A | 0.9300 | C16—H16A | 0.9600 |
| C3—C4 | 1.403 (2) | C16—H16B | 0.9600 |
| C4—C5 | 1.369 (2) | C16—H16C | 0.9600 |
| C5—C6 | 1.382 (2) | ||
| C3—O1—C7 | 117.57 (14) | H7B—C7—H7C | 109.5 |
| C4—O2—H2 | 109.5 | N1—C8—C1 | 122.59 (15) |
| C13—O4—C16 | 117.99 (19) | N1—C8—H8 | 118.7 |
| H5B—O5—H5A | 109.9 (17) | C1—C8—H8 | 118.7 |
| C8—N1—N2 | 114.08 (13) | O3—C9—N2 | 120.79 (16) |
| C9—N2—N1 | 119.46 (14) | O3—C9—C10 | 122.43 (15) |
| C9—N2—H2B | 120.1 (14) | N2—C9—C10 | 116.78 (15) |
| N1—N2—H2B | 120.5 (14) | C11—C10—C15 | 117.57 (17) |
| C6—C1—C2 | 118.84 (15) | C11—C10—C9 | 118.60 (17) |
| C6—C1—C8 | 118.80 (15) | C15—C10—C9 | 123.83 (16) |
| C2—C1—C8 | 122.36 (15) | C10—C11—C12 | 121.5 (2) |
| C3—C2—C1 | 120.41 (15) | C10—C11—H11 | 119.3 |
| C3—C2—H2A | 119.8 | C12—C11—H11 | 119.3 |
| C1—C2—H2A | 119.8 | C13—C12—C11 | 119.72 (19) |
| O1—C3—C2 | 125.22 (15) | C13—C12—H12 | 120.1 |
| O1—C3—C4 | 114.67 (14) | C11—C12—H12 | 120.1 |
| C2—C3—C4 | 120.11 (14) | O4—C13—C12 | 125.08 (18) |
| O2—C4—C5 | 123.37 (15) | O4—C13—C14 | 115.25 (19) |
| O2—C4—C3 | 117.03 (14) | C12—C13—C14 | 119.67 (18) |
| C5—C4—C3 | 119.59 (15) | C15—C14—C13 | 120.01 (19) |
| C4—C5—C6 | 120.06 (16) | C15—C14—H14 | 120.0 |
| C4—C5—H5 | 120.0 | C13—C14—H14 | 120.0 |
| C6—C5—H5 | 120.0 | C14—C15—C10 | 121.56 (17) |
| C5—C6—C1 | 120.98 (16) | C14—C15—H15 | 119.2 |
| C5—C6—H6 | 119.5 | C10—C15—H15 | 119.2 |
| C1—C6—H6 | 119.5 | O4—C16—H16A | 109.5 |
| O1—C7—H7A | 109.5 | O4—C16—H16B | 109.5 |
| O1—C7—H7B | 109.5 | H16A—C16—H16B | 109.5 |
| H7A—C7—H7B | 109.5 | O4—C16—H16C | 109.5 |
| O1—C7—H7C | 109.5 | H16A—C16—H16C | 109.5 |
| H7A—C7—H7C | 109.5 | H16B—C16—H16C | 109.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O5—H5A···N1i | 0.85 (1) | 2.49 (2) | 3.1257 (18) | 133 (2) |
| O5—H5A···O3i | 0.85 (1) | 2.11 (1) | 2.8927 (18) | 154 (2) |
| O5—H5B···O3ii | 0.86 (1) | 1.88 (1) | 2.7401 (17) | 179 (2) |
| N2—H2B···O2i | 0.90 (1) | 2.19 (1) | 3.0398 (18) | 160 (2) |
| O2—H2···O5iii | 0.82 | 1.77 | 2.5775 (17) | 170 |
| Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y, z−1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O5—H5A···N1i | 0.85 (1) | 2.49 (2) | 3.1257 (18) | 133 (2) |
| O5—H5A···O3i | 0.85 (1) | 2.11 (1) | 2.8927 (18) | 154 (2) |
| O5—H5B···O3ii | 0.86 (1) | 1.88 (1) | 2.7401 (17) | 179 (2) |
| N2—H2B···O2i | 0.90 (1) | 2.19 (1) | 3.0398 (18) | 160 (2) |
| O2—H2···O5iii | 0.82 | 1.77 | 2.5775 (17) | 170 |
| Symmetry codes: (i) x−1/2, −y+1/2, z+1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, y, z−1. |
The authors acknowledge the Scientific Research Foundation of Shaanxi University of Technology (Project No. SLGQD0708).
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Schiff bases and their metal complexes have received much attention in recent years. As part of our investigation on the crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b,c), we report herein the crystal structure of the title new Schiff base compound, (I).
The title compound (Fig. 1), consists of a Schiff base molecule and a water molecule of crystallization. The bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Abdul Alhadi et al., 2009; Mohd Lair et al., 2009; Narayana et al., 2007). The dihedral angle between the two aromatic rings is 19.6 (2)°, indicating that they the molecule is twisted.
In the crystal structure, the molecules are linked into a three-dimensional network by intermolecular N—H···O, O—H···N and O—H···O hydrogen bonds (Table 1 and Fig. 2).