Acta Cryst. (2010). E66, o539 [ doi:10.1107/S1600536810002916 ]
In the title compound, C24H24N2O4·H2O, the dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 65.06 (9) and 3.02 (9)°. Strong intramolecular O-H
N hydrogen bonds generate S(6) ring motifs. The H atoms of the water molecule act as donors in the formation of bifurcated O-H(O,O) intermolecular hydrogen bonds with the O atoms of the hydroxy and methoxy groups with R12(5) ring motifs; these may influence the molecular conformation.
The title compound was synthesized by adding 3-methoxy-salicylaldehyde (4 mmol) to a solution of 4,5-dimethyl-o-phenylenediamine (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant yellow solution was filtered. Yellow single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.
H atoms of the hydroxy groups of the Schiff base and water were located in a difference Fourier map. Initially the O-H distances were restrained to 0.96 (1) and 0.98 (1) Å, respectively and in the final cycles of refinement these H atoms were allowed to ride on the parent O atom with Uiso(H) = 1.5 Ueq(O), see Table 1. The remaining H atoms were positioned geometrically with C-H = 0.93-0.96 Å and included in a riding model approximation with Uiso (H) = 1.2 or 1.5 Ueq (C). A rotating group model was used for the methyl groups.
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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) and PLATON (Spek, 2009).
![[Figure 1]](./lh2982fig1thm.gif)
| Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. Intra- and intermolecular hydrogen bonds are drawn as dashed lines. |
![[Figure 2]](./lh2982fig2thm.gif)
| Fig. 2. The crystal packing of the title compound wieved along the a-axis. Hydrogen bonds are shown as dashed lines. |
| C24H24N2O4·H2O | Z = 2 |
| Mr = 422.47 | F(000) = 448 |
| Triclinic, P1 | Dx = 1.292 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 8.7431 (5) Å | Cell parameters from 5124 reflections |
| b = 10.3049 (6) Å | θ = 2.2–25.0° |
| c = 13.6614 (7) Å | µ = 0.09 mm−1 |
| α = 69.556 (3)° | T = 296 K |
| β = 83.846 (3)° | Block, yellow |
| γ = 70.280 (3)° | 0.30 × 0.20 × 0.15 mm |
| V = 1085.6 (1) Å3 |
| Bruker SMART APEXII CCD area-detector diffractometer | 5369 independent reflections |
| Radiation source: fine-focus sealed tube | 2912 reflections with I > 2˘I) |
| graphite | Rint = 0.031 |
| φ and ω scans | θmax = 28.3°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | h = −11→11 |
| Tmin = 0.973, Tmax = 0.987 | k = −12→13 |
| 23270 measured reflections | l = −18→18 |
| 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.141 | H-atom parameters constrained |
| S = 1.00 | w = 1/[σ2(Fo2) + (0.0622P)2 + 0.1326P] where P = (Fo2 + 2Fc2)/3 |
| 5369 reflections | (Δ/σ)max < 0.001 |
| 284 parameters | Δρmax = 0.20 e Å−3 |
| 0 restraints | Δρmin = −0.18 e Å−3 |
| C24H24N2O4·H2O | γ = 70.280 (3)° |
| Mr = 422.47 | V = 1085.6 (1) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 8.7431 (5) Å | Mo Kα radiation |
| b = 10.3049 (6) Å | µ = 0.09 mm−1 |
| c = 13.6614 (7) Å | T = 296 K |
| α = 69.556 (3)° | 0.30 × 0.20 × 0.15 mm |
| β = 83.846 (3)° |
| Bruker SMART APEXII CCD area-detector diffractometer | 5369 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2912 reflections with I > 2˘I) |
| Tmin = 0.973, Tmax = 0.987 | Rint = 0.031 |
| 23270 measured reflections | θmax = 28.3° |
| R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
| wR(F2) = 0.141 | Δρmax = 0.20 e Å−3 |
| S = 1.00 | Δρmin = −0.18 e Å−3 |
| 5369 reflections | Absolute structure: ? |
| 284 parameters | Flack parameter: ? |
| 0 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 | 0.48196 (13) | 0.46281 (13) | 0.27727 (9) | 0.0574 (3) | |
| H1 | 0.5531 | 0.4027 | 0.3362 | 0.086* | |
| O2 | 0.58907 (14) | 0.10375 (12) | 0.31399 (9) | 0.0563 (3) | |
| H2 | 0.6463 | 0.1102 | 0.3678 | 0.084* | |
| O3 | 0.34071 (17) | 0.62867 (15) | 0.09838 (10) | 0.0749 (4) | |
| O4 | 0.45471 (16) | 0.01221 (14) | 0.20011 (10) | 0.0692 (4) | |
| N1 | 0.74540 (15) | 0.32782 (13) | 0.39027 (10) | 0.0436 (3) | |
| N2 | 0.74691 (15) | 0.04912 (14) | 0.47979 (10) | 0.0438 (3) | |
| C1 | 0.5789 (2) | 0.51020 (17) | 0.19880 (12) | 0.0465 (4) | |
| C2 | 0.5055 (2) | 0.59934 (18) | 0.10105 (13) | 0.0549 (5) | |
| C3 | 0.5987 (3) | 0.6496 (2) | 0.01908 (14) | 0.0687 (6) | |
| H3A | 0.5502 | 0.7081 | −0.0459 | 0.082* | |
| C4 | 0.7642 (3) | 0.6143 (2) | 0.03171 (15) | 0.0733 (6) | |
| H4A | 0.8262 | 0.6484 | −0.0249 | 0.088* | |
| C5 | 0.8378 (2) | 0.5294 (2) | 0.12719 (14) | 0.0630 (5) | |
| H5A | 0.9489 | 0.5076 | 0.1354 | 0.076* | |
| C6 | 0.7458 (2) | 0.47583 (17) | 0.21197 (12) | 0.0469 (4) | |
| C7 | 0.8237 (2) | 0.38539 (17) | 0.31301 (13) | 0.0466 (4) | |
| H7A | 0.9335 | 0.3692 | 0.3214 | 0.056* | |
| C8 | 0.82177 (17) | 0.24595 (16) | 0.48957 (11) | 0.0401 (4) | |
| C9 | 0.88484 (19) | 0.30867 (18) | 0.54329 (13) | 0.0475 (4) | |
| H9A | 0.8844 | 0.4046 | 0.5110 | 0.057* | |
| C10 | 0.94858 (19) | 0.2329 (2) | 0.64369 (13) | 0.0496 (4) | |
| C11 | 0.95310 (19) | 0.0878 (2) | 0.69018 (12) | 0.0507 (4) | |
| C12 | 0.88856 (19) | 0.02546 (18) | 0.63693 (12) | 0.0493 (4) | |
| H12A | 0.8914 | −0.0712 | 0.6685 | 0.059* | |
| C13 | 0.81949 (17) | 0.10333 (17) | 0.53748 (12) | 0.0410 (4) | |
| C14 | 0.74023 (18) | −0.08139 (17) | 0.51154 (13) | 0.0467 (4) | |
| H14A | 0.7864 | −0.1459 | 0.5759 | 0.056* | |
| C15 | 0.66348 (18) | −0.13050 (17) | 0.45037 (13) | 0.0455 (4) | |
| C16 | 0.6581 (2) | −0.27411 (18) | 0.48757 (15) | 0.0563 (5) | |
| H16A | 0.7039 | −0.3370 | 0.5524 | 0.068* | |
| C17 | 0.5870 (2) | −0.32238 (19) | 0.43002 (16) | 0.0605 (5) | |
| H17A | 0.5842 | −0.4179 | 0.4556 | 0.073* | |
| C18 | 0.5181 (2) | −0.2296 (2) | 0.33301 (16) | 0.0589 (5) | |
| H18A | 0.4699 | −0.2637 | 0.2940 | 0.071* | |
| C19 | 0.5206 (2) | −0.08833 (19) | 0.29418 (14) | 0.0517 (4) | |
| C20 | 0.59181 (18) | −0.03598 (17) | 0.35303 (13) | 0.0458 (4) | |
| C21 | 0.2574 (3) | 0.7227 (2) | 0.00270 (16) | 0.0918 (8) | |
| H21A | 0.1438 | 0.7335 | 0.0106 | 0.138* | |
| H21B | 0.3006 | 0.6814 | −0.0514 | 0.138* | |
| H21C | 0.2715 | 0.8168 | −0.0157 | 0.138* | |
| C22 | 0.4007 (3) | −0.0392 (3) | 0.13155 (17) | 0.0840 (7) | |
| H22A | 0.3546 | 0.0412 | 0.0697 | 0.126* | |
| H22B | 0.3198 | −0.0834 | 0.1654 | 0.126* | |
| H22C | 0.4908 | −0.1104 | 0.1129 | 0.126* | |
| C23 | 1.0072 (2) | 0.3092 (2) | 0.70012 (15) | 0.0693 (6) | |
| H23A | 0.9946 | 0.4077 | 0.6554 | 0.104* | |
| H23B | 1.1198 | 0.2580 | 0.7188 | 0.104* | |
| H23C | 0.9447 | 0.3106 | 0.7622 | 0.104* | |
| C24 | 1.0284 (2) | −0.0036 (3) | 0.79731 (14) | 0.0789 (7) | |
| H24A | 0.9768 | 0.0447 | 0.8466 | 0.118* | |
| H24B | 1.1423 | −0.0157 | 0.7950 | 0.118* | |
| H24C | 1.0137 | −0.0977 | 0.8183 | 0.118* | |
| O1W | 0.25045 (16) | 0.32247 (16) | 0.23580 (10) | 0.0795 (4) | |
| H1W | 0.2953 | 0.4012 | 0.2238 | 0.119* | |
| H2W | 0.3547 | 0.2463 | 0.2467 | 0.119* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0557 (7) | 0.0600 (8) | 0.0444 (7) | −0.0177 (6) | −0.0123 (6) | −0.0001 (6) |
| O2 | 0.0718 (8) | 0.0398 (7) | 0.0541 (7) | −0.0176 (6) | −0.0099 (6) | −0.0094 (5) |
| O3 | 0.0744 (9) | 0.0733 (9) | 0.0556 (8) | −0.0061 (7) | −0.0298 (7) | −0.0043 (7) |
| O4 | 0.0853 (9) | 0.0595 (8) | 0.0662 (9) | −0.0225 (7) | −0.0143 (7) | −0.0214 (7) |
| N1 | 0.0496 (8) | 0.0390 (7) | 0.0354 (7) | −0.0115 (6) | −0.0089 (6) | −0.0044 (6) |
| N2 | 0.0436 (7) | 0.0394 (8) | 0.0416 (8) | −0.0102 (6) | 0.0013 (6) | −0.0088 (6) |
| C1 | 0.0625 (10) | 0.0373 (9) | 0.0362 (9) | −0.0140 (8) | −0.0068 (8) | −0.0078 (7) |
| C2 | 0.0712 (12) | 0.0433 (10) | 0.0424 (10) | −0.0082 (9) | −0.0148 (9) | −0.0104 (8) |
| C3 | 0.1010 (17) | 0.0537 (12) | 0.0371 (10) | −0.0130 (11) | −0.0127 (10) | −0.0058 (9) |
| C4 | 0.0947 (17) | 0.0735 (14) | 0.0409 (11) | −0.0281 (12) | 0.0079 (10) | −0.0076 (10) |
| C5 | 0.0733 (12) | 0.0650 (12) | 0.0466 (11) | −0.0248 (10) | 0.0049 (9) | −0.0125 (9) |
| C6 | 0.0592 (10) | 0.0412 (9) | 0.0377 (9) | −0.0143 (8) | −0.0039 (8) | −0.0108 (7) |
| C7 | 0.0499 (9) | 0.0434 (9) | 0.0439 (10) | −0.0111 (8) | −0.0065 (8) | −0.0130 (8) |
| C8 | 0.0354 (8) | 0.0404 (9) | 0.0347 (8) | −0.0052 (6) | −0.0040 (6) | −0.0064 (7) |
| C9 | 0.0458 (9) | 0.0467 (10) | 0.0458 (10) | −0.0111 (7) | −0.0050 (7) | −0.0125 (8) |
| C10 | 0.0394 (9) | 0.0627 (11) | 0.0426 (9) | −0.0089 (8) | −0.0027 (7) | −0.0192 (9) |
| C11 | 0.0405 (9) | 0.0648 (12) | 0.0348 (9) | −0.0055 (8) | −0.0033 (7) | −0.0123 (8) |
| C12 | 0.0457 (9) | 0.0437 (9) | 0.0400 (9) | −0.0032 (7) | −0.0007 (7) | −0.0026 (7) |
| C13 | 0.0352 (8) | 0.0433 (9) | 0.0363 (8) | −0.0057 (7) | −0.0001 (6) | −0.0099 (7) |
| C14 | 0.0420 (9) | 0.0428 (10) | 0.0437 (9) | −0.0084 (7) | 0.0034 (7) | −0.0064 (8) |
| C15 | 0.0383 (8) | 0.0391 (9) | 0.0527 (10) | −0.0088 (7) | 0.0081 (7) | −0.0132 (8) |
| C16 | 0.0506 (10) | 0.0421 (10) | 0.0660 (12) | −0.0133 (8) | 0.0086 (9) | −0.0099 (9) |
| C17 | 0.0549 (11) | 0.0407 (10) | 0.0834 (14) | −0.0200 (8) | 0.0131 (10) | −0.0169 (10) |
| C18 | 0.0511 (10) | 0.0542 (11) | 0.0801 (14) | −0.0199 (9) | 0.0106 (10) | −0.0329 (11) |
| C19 | 0.0472 (9) | 0.0464 (10) | 0.0590 (11) | −0.0115 (8) | 0.0041 (8) | −0.0190 (9) |
| C20 | 0.0415 (9) | 0.0387 (9) | 0.0554 (10) | −0.0116 (7) | 0.0079 (8) | −0.0171 (8) |
| C21 | 0.1047 (17) | 0.0766 (15) | 0.0687 (14) | 0.0037 (13) | −0.0514 (13) | −0.0104 (12) |
| C22 | 0.1109 (18) | 0.0963 (17) | 0.0642 (14) | −0.0490 (14) | 0.0015 (12) | −0.0350 (13) |
| C23 | 0.0644 (12) | 0.0936 (16) | 0.0568 (12) | −0.0233 (11) | −0.0064 (9) | −0.0333 (11) |
| C24 | 0.0728 (13) | 0.0990 (17) | 0.0419 (11) | −0.0162 (12) | −0.0161 (9) | −0.0021 (11) |
| O1W | 0.0693 (9) | 0.0887 (11) | 0.0677 (9) | −0.0254 (8) | −0.0075 (7) | −0.0086 (8) |
| O1—C1 | 1.3511 (19) | C11—C12 | 1.385 (2) |
| O1—H1 | 0.9574 | C11—C24 | 1.512 (2) |
| O2—C20 | 1.3422 (18) | C12—C13 | 1.394 (2) |
| O2—H2 | 0.9642 | C12—H12A | 0.9300 |
| O3—C2 | 1.371 (2) | C14—C15 | 1.432 (2) |
| O3—C21 | 1.422 (2) | C14—H14A | 0.9300 |
| O4—C19 | 1.372 (2) | C15—C16 | 1.402 (2) |
| O4—C22 | 1.411 (2) | C15—C20 | 1.404 (2) |
| N1—C7 | 1.271 (2) | C16—C17 | 1.356 (3) |
| N1—C8 | 1.4186 (18) | C16—H16A | 0.9300 |
| N2—C14 | 1.281 (2) | C17—C18 | 1.389 (3) |
| N2—C13 | 1.411 (2) | C17—H17A | 0.9300 |
| C1—C6 | 1.396 (2) | C18—C19 | 1.372 (2) |
| C1—C2 | 1.403 (2) | C18—H18A | 0.9300 |
| C2—C3 | 1.367 (3) | C19—C20 | 1.401 (2) |
| C3—C4 | 1.382 (3) | C21—H21A | 0.9600 |
| C3—H3A | 0.9300 | C21—H21B | 0.9600 |
| C4—C5 | 1.373 (3) | C21—H21C | 0.9600 |
| C4—H4A | 0.9300 | C22—H22A | 0.9600 |
| C5—C6 | 1.395 (2) | C22—H22B | 0.9600 |
| C5—H5A | 0.9300 | C22—H22C | 0.9600 |
| C6—C7 | 1.453 (2) | C23—H23A | 0.9600 |
| C7—H7A | 0.9300 | C23—H23B | 0.9600 |
| C8—C9 | 1.385 (2) | C23—H23C | 0.9600 |
| C8—C13 | 1.391 (2) | C24—H24A | 0.9600 |
| C9—C10 | 1.387 (2) | C24—H24B | 0.9600 |
| C9—H9A | 0.9300 | C24—H24C | 0.9600 |
| C10—C11 | 1.394 (2) | O1W—H1W | 0.9731 |
| C10—C23 | 1.502 (2) | O1W—H2W | 0.9664 |
| C1—O1—H1 | 105.3 | N2—C14—H14A | 119.2 |
| C20—O2—H2 | 101.6 | C15—C14—H14A | 119.2 |
| C2—O3—C21 | 117.48 (16) | C16—C15—C20 | 119.09 (16) |
| C19—O4—C22 | 117.25 (15) | C16—C15—C14 | 120.16 (16) |
| C7—N1—C8 | 120.70 (13) | C20—C15—C14 | 120.75 (15) |
| C14—N2—C13 | 123.85 (14) | C17—C16—C15 | 120.75 (17) |
| O1—C1—C6 | 122.82 (14) | C17—C16—H16A | 119.6 |
| O1—C1—C2 | 117.44 (16) | C15—C16—H16A | 119.6 |
| C6—C1—C2 | 119.74 (16) | C16—C17—C18 | 120.21 (17) |
| C3—C2—O3 | 125.95 (16) | C16—C17—H17A | 119.9 |
| C3—C2—C1 | 119.61 (18) | C18—C17—H17A | 119.9 |
| O3—C2—C1 | 114.44 (16) | C19—C18—C17 | 120.71 (18) |
| C2—C3—C4 | 120.71 (17) | C19—C18—H18A | 119.6 |
| C2—C3—H3A | 119.6 | C17—C18—H18A | 119.6 |
| C4—C3—H3A | 119.6 | C18—C19—O4 | 125.26 (17) |
| C5—C4—C3 | 120.52 (19) | C18—C19—C20 | 119.90 (17) |
| C5—C4—H4A | 119.7 | O4—C19—C20 | 114.83 (15) |
| C3—C4—H4A | 119.7 | O2—C20—C19 | 118.51 (15) |
| C4—C5—C6 | 119.97 (19) | O2—C20—C15 | 122.17 (15) |
| C4—C5—H5A | 120.0 | C19—C20—C15 | 119.32 (15) |
| C6—C5—H5A | 120.0 | O3—C21—H21A | 109.5 |
| C5—C6—C1 | 119.44 (15) | O3—C21—H21B | 109.5 |
| C5—C6—C7 | 120.03 (16) | H21A—C21—H21B | 109.5 |
| C1—C6—C7 | 120.54 (15) | O3—C21—H21C | 109.5 |
| N1—C7—C6 | 121.65 (15) | H21A—C21—H21C | 109.5 |
| N1—C7—H7A | 119.2 | H21B—C21—H21C | 109.5 |
| C6—C7—H7A | 119.2 | O4—C22—H22A | 109.5 |
| C9—C8—C13 | 119.56 (14) | O4—C22—H22B | 109.5 |
| C9—C8—N1 | 121.60 (14) | H22A—C22—H22B | 109.5 |
| C13—C8—N1 | 118.58 (14) | O4—C22—H22C | 109.5 |
| C8—C9—C10 | 122.06 (16) | H22A—C22—H22C | 109.5 |
| C8—C9—H9A | 119.0 | H22B—C22—H22C | 109.5 |
| C10—C9—H9A | 119.0 | C10—C23—H23A | 109.5 |
| C9—C10—C11 | 118.54 (16) | C10—C23—H23B | 109.5 |
| C9—C10—C23 | 119.63 (17) | H23A—C23—H23B | 109.5 |
| C11—C10—C23 | 121.82 (15) | C10—C23—H23C | 109.5 |
| C12—C11—C10 | 119.41 (14) | H23A—C23—H23C | 109.5 |
| C12—C11—C24 | 119.24 (17) | H23B—C23—H23C | 109.5 |
| C10—C11—C24 | 121.35 (17) | C11—C24—H24A | 109.5 |
| C11—C12—C13 | 121.97 (16) | C11—C24—H24B | 109.5 |
| C11—C12—H12A | 119.0 | H24A—C24—H24B | 109.5 |
| C13—C12—H12A | 119.0 | C11—C24—H24C | 109.5 |
| C8—C13—C12 | 118.37 (15) | H24A—C24—H24C | 109.5 |
| C8—C13—N2 | 116.34 (13) | H24B—C24—H24C | 109.5 |
| C12—C13—N2 | 125.28 (15) | H1W—O1W—H2W | 95.0 |
| N2—C14—C15 | 121.63 (15) | ||
| C21—O3—C2—C3 | −1.7 (3) | C10—C11—C12—C13 | 0.3 (2) |
| C21—O3—C2—C1 | 177.79 (17) | C24—C11—C12—C13 | −179.15 (15) |
| O1—C1—C2—C3 | −179.75 (16) | C9—C8—C13—C12 | −3.1 (2) |
| C6—C1—C2—C3 | 1.2 (3) | N1—C8—C13—C12 | −177.31 (14) |
| O1—C1—C2—O3 | 0.7 (2) | C9—C8—C13—N2 | 177.27 (13) |
| C6—C1—C2—O3 | −178.33 (15) | N1—C8—C13—N2 | 3.0 (2) |
| O3—C2—C3—C4 | 178.97 (18) | C11—C12—C13—C8 | 2.5 (2) |
| C1—C2—C3—C4 | −0.5 (3) | C11—C12—C13—N2 | −177.89 (14) |
| C2—C3—C4—C5 | −0.7 (3) | C14—N2—C13—C8 | 177.54 (14) |
| C3—C4—C5—C6 | 1.1 (3) | C14—N2—C13—C12 | −2.1 (2) |
| C4—C5—C6—C1 | −0.4 (3) | C13—N2—C14—C15 | 179.30 (14) |
| C4—C5—C6—C7 | 179.75 (18) | N2—C14—C15—C16 | −179.90 (15) |
| O1—C1—C6—C5 | −179.76 (16) | N2—C14—C15—C20 | −0.3 (2) |
| C2—C1—C6—C5 | −0.7 (2) | C20—C15—C16—C17 | 1.0 (2) |
| O1—C1—C6—C7 | 0.1 (2) | C14—C15—C16—C17 | −179.45 (16) |
| C2—C1—C6—C7 | 179.11 (15) | C15—C16—C17—C18 | 0.0 (3) |
| C8—N1—C7—C6 | −176.84 (14) | C16—C17—C18—C19 | −0.2 (3) |
| C5—C6—C7—N1 | −175.85 (16) | C17—C18—C19—O4 | −179.23 (16) |
| C1—C6—C7—N1 | 4.3 (2) | C17—C18—C19—C20 | −0.6 (3) |
| C7—N1—C8—C9 | 61.2 (2) | C22—O4—C19—C18 | −9.5 (3) |
| C7—N1—C8—C13 | −124.72 (17) | C22—O4—C19—C20 | 171.84 (16) |
| C13—C8—C9—C10 | 0.9 (2) | C18—C19—C20—O2 | −178.50 (15) |
| N1—C8—C9—C10 | 174.99 (14) | O4—C19—C20—O2 | 0.3 (2) |
| C8—C9—C10—C11 | 1.9 (2) | C18—C19—C20—C15 | 1.5 (2) |
| C8—C9—C10—C23 | −176.79 (15) | O4—C19—C20—C15 | −179.69 (14) |
| C9—C10—C11—C12 | −2.5 (2) | C16—C15—C20—O2 | 178.33 (14) |
| C23—C10—C11—C12 | 176.17 (15) | C14—C15—C20—O2 | −1.3 (2) |
| C9—C10—C11—C24 | 176.97 (16) | C16—C15—C20—C19 | −1.7 (2) |
| C23—C10—C11—C24 | −4.4 (3) | C14—C15—C20—C19 | 178.70 (15) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.96 | 1.72 | 2.5929 (18) | 150 |
| O1W—H1W···O1 | 0.97 | 2.21 | 3.050 (2) | 144 |
| O1W—H1W···O3 | 0.97 | 2.50 | 3.366 (2) | 148 |
| O2—H2···N2 | 0.96 | 1.66 | 2.5704 (18) | 156 |
| O1W—H2W···O2 | 0.97 | 2.15 | 3.079 (2) | 160 |
| O1W—H2W···O4 | 0.97 | 2.55 | 3.271 (2) | 131 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.96 | 1.72 | 2.5929 (18) | 150 |
| O1W—H1W···O1 | 0.97 | 2.21 | 3.050 (2) | 144 |
| O1W—H1W···O3 | 0.97 | 2.50 | 3.366 (2) | 148 |
| O2—H2···N2 | 0.96 | 1.66 | 2.5704 (18) | 156 |
| O1W—H2W···O2 | 0.97 | 2.15 | 3.079 (2) | 160 |
| O1W—H2W···O4 | 0.97 | 2.55 | 3.271 (2) | 131 |
HK and AJ thank PNU for financial support. IUK thanks GC University of Lahore, Pakistan, for the research facilities.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
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Schiff base ligands are one of the most prevalent systems in coordination chemistry. They can show thermochromic and photochromic properties (Hajioudis et al. (1987). As part of a general study of tetradenate Schiff bases (Kargar et al. 2009), we have determined the crystal structure of the title compound.
The asymmetric unit of the title compound, Fig. 1, comprises a Schiff base ligand and a water molecule of crystallization. The bond lengths (Allen et al., 1987) and angles are within the normal ranges and comparable to previously reported structures (Eltayeb & Ahmed, 2005; Eltayeb et al., 2007; Cakir et al. 2002; Kargar et al., 2009 ). The dihedral angles between the central benzene ring and the two outer benzene rings of the Schiff base are 65.06 (9) and 3.02 (9)°. Strong intramolecular O—H···N hydrogen bonds generate S(6) ring motifs (Bernstein et al., 1995). The hydrogen atoms of the water molecule form bifurcated intermolecular hydrogen bonds with the oxygen atoms of the hydroxy and methoxy groups with R21(5) ring motifs (Bernstein et al., 1995), which may, in part, influence the molecular configuration (Table 1). A view of part of the crystal structure is shown in Fig .2.