Acta Cryst. (2009). E65, o29 [ doi:10.1107/S1600536808040117 ]
Single crystals of the title compound, C16H14N2O5·H2O, were obtained from a condensation reaction of 1,3-benzodioxole-5-carbohydrazide and 3-methoxysalicylaldehyde in a 95% ethanol solution. The asymmetric unit consists of a Schiff base molecule, which assumes an E configuration with respect to the C=N bond, and a water molecule of crystallization. The dihedral angle between the two substituted benzene rings is 12.7 (2)°. In the crystal structure, molecules are linked through intermolecular N-H
O and O-HO hydrogen bonds, forming layers parallel to the bc plane.
The title compound was prepared by Schiff base condensation reaction of 1,3-benzodioxole-5-carbohydrazide (1.0 mmol) and 3-methoxysalicylaldehyde (1.0 mmol) in a 95% ethanol solution (50 ml). Needle colorless crystals were formed by gradual evaporation of the solution in air for a few days.
The imino H atom was located in a difference map and refined with a N–H distance restraint of 0.90 (1) Å. The water H atoms were also located in a difference map and refined with O–H and H···H distances restraints of 0.85 (1) and 1.37 (2) Å, respectively. The other H atoms were positioned geometrically [C–H = 0.93–0.97 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl). A rotating group model was used for the methyl group. In the absence of significant anomalous scattering effects, 1034 Friedel pairs were merged.
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: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./sj2559fig1thm.gif)
| Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
![[Figure 2]](./sj2559fig2thm.gif)
| Fig. 2. The crystal packing of the title compound, viewed down the a axis. |
| C16H14N2O5·H2O | F(000) = 696 |
| Mr = 332.31 | Dx = 1.486 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 3222 reflections |
| a = 4.792 (2) Å | θ = 2.4–25.6° |
| b = 12.916 (3) Å | µ = 0.12 mm−1 |
| c = 24.002 (6) Å | T = 298 K |
| V = 1485.6 (7) Å3 | Cut from needle, colorless |
| Z = 4 | 0.23 × 0.20 × 0.20 mm |
| Bruker SMART 1K CCD area-detector diffractometer | 1907 independent reflections |
| Radiation source: fine-focus sealed tube | 1639 reflections with I > 2σ(I) |
| graphite | Rint = 0.030 |
| ω scans | θmax = 27.0°, θmin = 1.7° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
| Tmin = 0.974, Tmax = 0.977 | k = −16→13 |
| 8595 measured reflections | l = −30→28 |
| 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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0385P)2 + 0.1335P] where P = (Fo2 + 2Fc2)/3 |
| 1907 reflections | (Δ/σ)max < 0.001 |
| 228 parameters | Δρmax = 0.13 e Å−3 |
| 4 restraints | Δρmin = −0.13 e Å−3 |
| C16H14N2O5·H2O | V = 1485.6 (7) Å3 |
| Mr = 332.31 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα radiation |
| a = 4.792 (2) Å | µ = 0.12 mm−1 |
| b = 12.916 (3) Å | T = 298 K |
| c = 24.002 (6) Å | 0.23 × 0.20 × 0.20 mm |
| Bruker SMART 1K CCD area-detector diffractometer | 1907 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1639 reflections with I > 2σ(I) |
| Tmin = 0.974, Tmax = 0.977 | Rint = 0.030 |
| 8595 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.076 | Δρmax = 0.13 e Å−3 |
| S = 1.05 | Δρmin = −0.13 e Å−3 |
| 1907 reflections | Absolute structure: ? |
| 228 parameters | Flack parameter: ? |
| 4 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 | ||
| O1 | 0.9802 (3) | 0.80320 (10) | 0.83305 (6) | 0.0447 (4) | |
| H1 | 0.8775 | 0.8121 | 0.8061 | 0.067* | |
| O2 | 0.3794 (4) | 0.78499 (11) | 0.69933 (6) | 0.0563 (5) | |
| O3 | 1.3470 (3) | 0.79317 (11) | 0.91162 (6) | 0.0489 (4) | |
| O4 | −0.3191 (4) | 0.81446 (12) | 0.53841 (6) | 0.0599 (5) | |
| O5 | −0.3991 (3) | 0.98897 (11) | 0.52200 (6) | 0.0490 (4) | |
| O6 | 0.4857 (4) | 0.67908 (12) | 0.79533 (6) | 0.0528 (4) | |
| N1 | 0.7019 (4) | 0.92306 (13) | 0.75678 (6) | 0.0368 (4) | |
| N2 | 0.5153 (4) | 0.95059 (13) | 0.71517 (7) | 0.0374 (4) | |
| C1 | 1.0510 (4) | 0.98797 (15) | 0.82015 (7) | 0.0349 (4) | |
| C2 | 1.1069 (4) | 0.89400 (14) | 0.84647 (8) | 0.0330 (4) | |
| C3 | 1.3082 (4) | 0.88967 (15) | 0.88912 (8) | 0.0360 (4) | |
| C4 | 1.4481 (5) | 0.97831 (16) | 0.90522 (8) | 0.0415 (5) | |
| H4 | 1.5789 | 0.9754 | 0.9338 | 0.050* | |
| C5 | 1.3937 (5) | 1.07197 (16) | 0.87871 (8) | 0.0449 (5) | |
| H5 | 1.4897 | 1.1314 | 0.8893 | 0.054* | |
| C6 | 1.1978 (5) | 1.07680 (15) | 0.83680 (8) | 0.0418 (5) | |
| H6 | 1.1624 | 1.1397 | 0.8193 | 0.050* | |
| C7 | 0.8453 (5) | 0.99888 (16) | 0.77596 (8) | 0.0388 (5) | |
| H7 | 0.8163 | 1.0643 | 0.7608 | 0.047* | |
| C8 | 0.3608 (5) | 0.87806 (15) | 0.68878 (7) | 0.0371 (5) | |
| C9 | 0.1638 (5) | 0.91647 (14) | 0.64528 (7) | 0.0330 (4) | |
| C10 | 0.0244 (5) | 0.84061 (15) | 0.61392 (8) | 0.0383 (5) | |
| H10 | 0.0559 | 0.7705 | 0.6200 | 0.046* | |
| C11 | −0.1597 (5) | 0.87353 (15) | 0.57404 (8) | 0.0385 (5) | |
| C12 | −0.2088 (5) | 0.97742 (15) | 0.56457 (7) | 0.0359 (4) | |
| C13 | −0.0799 (5) | 1.05292 (15) | 0.59480 (8) | 0.0412 (5) | |
| H13 | −0.1162 | 1.1227 | 0.5885 | 0.049* | |
| C14 | 0.1088 (5) | 1.02087 (15) | 0.63555 (8) | 0.0386 (5) | |
| H14 | 0.2004 | 1.0705 | 0.6568 | 0.046* | |
| C15 | −0.4686 (6) | 0.88603 (18) | 0.50433 (8) | 0.0497 (6) | |
| H15A | −0.6678 | 0.8746 | 0.5080 | 0.060* | |
| H15B | −0.4179 | 0.8765 | 0.4655 | 0.060* | |
| C16 | 1.5697 (5) | 0.78022 (19) | 0.95022 (9) | 0.0522 (6) | |
| H16A | 1.5365 | 0.8226 | 0.9824 | 0.078* | |
| H16B | 1.7421 | 0.8005 | 0.9330 | 0.078* | |
| H16C | 1.5806 | 0.7089 | 0.9613 | 0.078* | |
| H2 | 0.499 (7) | 1.0186 (9) | 0.7078 (10) | 0.080* | |
| H6A | 0.474 (6) | 0.7133 (18) | 0.7649 (6) | 0.080* | |
| H6B | 0.366 (5) | 0.706 (2) | 0.8170 (8) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0460 (9) | 0.0381 (8) | 0.0500 (9) | −0.0062 (7) | −0.0165 (7) | −0.0011 (7) |
| O2 | 0.0772 (12) | 0.0351 (8) | 0.0567 (9) | 0.0061 (9) | −0.0217 (9) | 0.0055 (7) |
| O3 | 0.0506 (10) | 0.0414 (8) | 0.0548 (8) | −0.0064 (8) | −0.0222 (8) | 0.0105 (7) |
| O4 | 0.0706 (12) | 0.0453 (8) | 0.0638 (10) | 0.0007 (9) | −0.0276 (10) | −0.0127 (8) |
| O5 | 0.0524 (10) | 0.0516 (9) | 0.0430 (8) | 0.0055 (8) | −0.0141 (8) | −0.0009 (7) |
| O6 | 0.0684 (12) | 0.0394 (8) | 0.0505 (9) | 0.0050 (9) | −0.0110 (9) | 0.0016 (7) |
| N1 | 0.0366 (9) | 0.0429 (9) | 0.0308 (8) | 0.0065 (8) | −0.0034 (8) | 0.0020 (7) |
| N2 | 0.0394 (10) | 0.0373 (9) | 0.0356 (8) | 0.0034 (8) | −0.0070 (8) | 0.0044 (7) |
| C1 | 0.0326 (11) | 0.0389 (10) | 0.0333 (9) | 0.0042 (9) | 0.0022 (8) | −0.0020 (8) |
| C2 | 0.0319 (10) | 0.0339 (9) | 0.0332 (9) | −0.0007 (9) | −0.0005 (8) | −0.0039 (8) |
| C3 | 0.0357 (11) | 0.0380 (10) | 0.0344 (9) | −0.0002 (10) | −0.0025 (9) | 0.0003 (8) |
| C4 | 0.0389 (12) | 0.0462 (11) | 0.0393 (10) | −0.0042 (10) | −0.0058 (10) | −0.0047 (9) |
| C5 | 0.0442 (13) | 0.0380 (11) | 0.0525 (12) | −0.0065 (10) | −0.0029 (11) | −0.0063 (9) |
| C6 | 0.0450 (13) | 0.0335 (10) | 0.0469 (11) | 0.0031 (10) | 0.0012 (11) | 0.0001 (9) |
| C7 | 0.0418 (12) | 0.0381 (10) | 0.0365 (10) | 0.0068 (11) | −0.0019 (9) | 0.0038 (8) |
| C8 | 0.0424 (12) | 0.0366 (10) | 0.0323 (10) | 0.0055 (10) | 0.0005 (9) | 0.0019 (8) |
| C9 | 0.0356 (11) | 0.0333 (9) | 0.0302 (9) | 0.0016 (9) | 0.0021 (8) | 0.0020 (7) |
| C10 | 0.0446 (12) | 0.0325 (10) | 0.0377 (10) | 0.0031 (10) | −0.0014 (10) | 0.0007 (8) |
| C11 | 0.0419 (13) | 0.0376 (10) | 0.0360 (10) | −0.0013 (10) | −0.0009 (9) | −0.0064 (8) |
| C12 | 0.0357 (11) | 0.0438 (11) | 0.0283 (9) | 0.0039 (9) | 0.0002 (9) | 0.0030 (8) |
| C13 | 0.0508 (13) | 0.0314 (10) | 0.0414 (10) | 0.0050 (10) | −0.0056 (10) | 0.0021 (9) |
| C14 | 0.0442 (12) | 0.0345 (10) | 0.0372 (10) | −0.0001 (9) | −0.0066 (10) | −0.0010 (8) |
| C15 | 0.0480 (14) | 0.0602 (14) | 0.0410 (11) | −0.0083 (13) | −0.0079 (11) | 0.0006 (10) |
| C16 | 0.0456 (13) | 0.0630 (14) | 0.0478 (12) | −0.0021 (12) | −0.0128 (11) | 0.0145 (11) |
| O1—C2 | 1.359 (2) | C4—H4 | 0.9300 |
| O1—H1 | 0.8200 | C5—C6 | 1.377 (3) |
| O2—C8 | 1.232 (2) | C5—H5 | 0.9300 |
| O3—C3 | 1.371 (2) | C6—H6 | 0.9300 |
| O3—C16 | 1.423 (2) | C7—H7 | 0.9300 |
| O4—C11 | 1.377 (2) | C8—C9 | 1.492 (3) |
| O4—C15 | 1.427 (3) | C9—C14 | 1.394 (3) |
| O5—C12 | 1.378 (2) | C9—C10 | 1.405 (3) |
| O5—C15 | 1.435 (3) | C10—C11 | 1.369 (3) |
| O6—H6A | 0.857 (10) | C10—H10 | 0.9300 |
| O6—H6B | 0.848 (10) | C11—C12 | 1.381 (3) |
| N1—C7 | 1.282 (3) | C12—C13 | 1.363 (3) |
| N1—N2 | 1.387 (2) | C13—C14 | 1.395 (3) |
| N2—C8 | 1.352 (3) | C13—H13 | 0.9300 |
| N2—H2 | 0.899 (10) | C14—H14 | 0.9300 |
| C1—C2 | 1.394 (3) | C15—H15A | 0.9700 |
| C1—C6 | 1.404 (3) | C15—H15B | 0.9700 |
| C1—C7 | 1.455 (3) | C16—H16A | 0.9600 |
| C2—C3 | 1.408 (3) | C16—H16B | 0.9600 |
| C3—C4 | 1.382 (3) | C16—H16C | 0.9600 |
| C4—C5 | 1.392 (3) | ||
| C2—O1—H1 | 109.5 | N2—C8—C9 | 116.35 (16) |
| C3—O3—C16 | 117.72 (17) | C14—C9—C10 | 119.66 (18) |
| C11—O4—C15 | 105.99 (16) | C14—C9—C8 | 123.96 (18) |
| C12—O5—C15 | 105.81 (15) | C10—C9—C8 | 116.36 (17) |
| H6A—O6—H6B | 105.5 (19) | C11—C10—C9 | 117.68 (18) |
| C7—N1—N2 | 114.10 (16) | C11—C10—H10 | 121.2 |
| C8—N2—N1 | 120.86 (16) | C9—C10—H10 | 121.2 |
| C8—N2—H2 | 122.6 (19) | C10—C11—O4 | 128.26 (18) |
| N1—N2—H2 | 116.6 (19) | C10—C11—C12 | 121.75 (19) |
| C2—C1—C6 | 119.08 (18) | O4—C11—C12 | 109.99 (18) |
| C2—C1—C7 | 123.01 (19) | C13—C12—O5 | 128.10 (17) |
| C6—C1—C7 | 117.90 (18) | C13—C12—C11 | 122.03 (18) |
| O1—C2—C1 | 123.91 (17) | O5—C12—C11 | 109.86 (17) |
| O1—C2—C3 | 116.37 (16) | C12—C13—C14 | 117.03 (17) |
| C1—C2—C3 | 119.72 (17) | C12—C13—H13 | 121.5 |
| O3—C3—C4 | 125.24 (18) | C14—C13—H13 | 121.5 |
| O3—C3—C2 | 114.56 (17) | C9—C14—C13 | 121.83 (18) |
| C4—C3—C2 | 120.20 (18) | C9—C14—H14 | 119.1 |
| C3—C4—C5 | 120.09 (19) | C13—C14—H14 | 119.1 |
| C3—C4—H4 | 120.0 | O4—C15—O5 | 108.32 (17) |
| C5—C4—H4 | 120.0 | O4—C15—H15A | 110.0 |
| C6—C5—C4 | 120.1 (2) | O5—C15—H15A | 110.0 |
| C6—C5—H5 | 120.0 | O4—C15—H15B | 110.0 |
| C4—C5—H5 | 120.0 | O5—C15—H15B | 110.0 |
| C5—C6—C1 | 120.83 (19) | H15A—C15—H15B | 108.4 |
| C5—C6—H6 | 119.6 | O3—C16—H16A | 109.5 |
| C1—C6—H6 | 119.6 | O3—C16—H16B | 109.5 |
| N1—C7—C1 | 123.44 (18) | H16A—C16—H16B | 109.5 |
| N1—C7—H7 | 118.3 | O3—C16—H16C | 109.5 |
| C1—C7—H7 | 118.3 | H16A—C16—H16C | 109.5 |
| O2—C8—N2 | 122.73 (19) | H16B—C16—H16C | 109.5 |
| O2—C8—C9 | 120.92 (19) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.82 | 2.04 | 2.743 (2) | 143 |
| O1—H1···O6 | 0.82 | 2.56 | 3.001 (2) | 115 |
| N2—H2···O6i | 0.90 (1) | 2.08 (1) | 2.962 (2) | 168 (3) |
| O6—H6A···O2 | 0.86 (1) | 1.88 (1) | 2.728 (2) | 170 (3) |
| O6—H6B···O1ii | 0.85 (1) | 2.27 (2) | 3.043 (2) | 152 (2) |
| O6—H6B···O3ii | 0.85 (1) | 2.54 (2) | 3.226 (2) | 139 (2) |
| Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.82 | 2.04 | 2.743 (2) | 143 |
| O1—H1···O6 | 0.82 | 2.56 | 3.001 (2) | 115 |
| N2—H2···O6i | 0.90 (1) | 2.08 (1) | 2.962 (2) | 168 (3) |
| O6—H6A···O2 | 0.86 (1) | 1.88 (1) | 2.728 (2) | 170 (3) |
| O6—H6B···O1ii | 0.85 (1) | 2.27 (2) | 3.043 (2) | 152 (2) |
| O6—H6B···O3ii | 0.85 (1) | 2.54 (2) | 3.226 (2) | 139 (2) |
| Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z. |
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Yehye, W. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o960.
Hydrazone compounds, derived from the condensation reactions of aldehydes with hydrazides, show interesting biological properties (Okabe et al., 1993; Bedia et al., 2006; Rollas et al., 2002). Recently, a large number of hydrazone derivatives have been reported (Shan et al., 2008; Fun et al., 2008; Qu et al., 2008; Yehye et al., 2008). We report here the structure of a new hydrazone compound, I, Fig. 1, with a Schiff base molecule, which assumes an E configuration with respect to the C═N bond and a water molecule in the asymmetric unit. The dihedral angle between the two substituted benzene rings is 12.7 (2)°. All the bond lengths are within normal ranges (Allen et al., 1987).
In the crystal structure, molecules are linked through intermolecular N—H···O and O—H···O hydrogen bonds (Table 1), forming layers parallel to the bc direction (Fig. 2).