Acta Cryst. (2008). E64, o865 [ doi:10.1107/S1600536808010118 ]
In the title compound, C17H21N3O3S, the dihedral angle between the aromatic ring planes is 84.2 (2)°. The pendant ethyl groups of the -N(C2H5)2 group are disordered over two sets of positions in a 0.84 (2):0.16 (2) ratio. The molecular conformation is stabilized by an intramolecular O-H
N hydrogen bond, and intermolecular N-HO bonds lead to [010] chains in the crystal structure.
3 mmol of p-(diethylamino)salicylaldehyde (3 mmol) was added to a solution of benzenesulfonyl hydrazide (3 mmol) in 10 ml of 95% ethanol. The mixture was continuously stirred for 4 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 67%). Colourless plates of (I) were obtained by evaporation from a methanol solution after several days.
The H atoms were placed geometrically (C—H = 0.93–0.96 Å, N—H = 0.86 Å, O—H = 0.82Å) and refined as riding with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(methyl C, O).
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 (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./hb2720fig1thm.gif)
| Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids for the non-hydrogen atoms. Only the major disorder component is shown and the hydrogen bond is indicated by a double-dashed line. |
| C17H21N3O3S | Dx = 1.331 Mg m−3 |
| Mr = 347.43 | Mo Kα radiation λ = 0.71073 Å |
| Orthorhombic, Pbcn | Cell parameters from 3546 reflections |
| a = 29.874 (3) Å | θ = 2.7–21.4º |
| b = 7.5153 (12) Å | µ = 0.21 mm−1 |
| c = 15.4456 (19) Å | T = 293 (2) K |
| V = 3467.8 (8) Å3 | Plate, colourless |
| Z = 8 | 0.43 × 0.38 × 0.04 mm |
| F000 = 1472 |
| Bruker SMART CCD diffractometer | 3052 independent reflections |
| Radiation source: fine-focus sealed tube | 2061 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.048 |
| T = 293(2) K | θmax = 25.0º |
| ω scans | θmin = 2.6º |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −35→34 |
| Tmin = 0.916, Tmax = 0.992 | k = −8→7 |
| 16321 measured reflections | l = −18→14 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.069 | H-atom parameters constrained |
| wR(F2) = 0.175 | w = 1/[σ2(Fo2) + (0.0453P)2 + 7.4306P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max = 0.001 |
| 3052 reflections | Δρmax = 0.44 e Å−3 |
| 258 parameters | Δρmin = −0.30 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C17H21N3O3S | V = 3467.8 (8) Å3 |
| Mr = 347.43 | Z = 8 |
| Orthorhombic, Pbcn | Mo Kα |
| a = 29.874 (3) Å | µ = 0.21 mm−1 |
| b = 7.5153 (12) Å | T = 293 (2) K |
| c = 15.4456 (19) Å | 0.43 × 0.38 × 0.04 mm |
| Bruker SMART CCD diffractometer | 3052 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | 2061 reflections with I > 2σ(I) |
| Tmin = 0.916, Tmax = 0.992 | Rint = 0.048 |
| 16321 measured reflections |
| R[F2 > 2σ(F2)] = 0.069 | 258 parameters |
| wR(F2) = 0.175 | H-atom parameters constrained |
| S = 1.08 | Δρmax = 0.44 e Å−3 |
| 3052 reflections | Δρmin = −0.30 e Å−3 |
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 | Occ. (<1) | |
| N1 | 0.31274 (11) | 0.2572 (5) | 0.9493 (2) | 0.0502 (9) | |
| H1 | 0.2949 | 0.3499 | 0.9363 | 0.060* | |
| N2 | 0.35710 (11) | 0.3011 (5) | 0.9253 (2) | 0.0512 (9) | |
| N3 | 0.54548 (13) | 0.6991 (6) | 0.8710 (3) | 0.0794 (14) | |
| O1 | 0.24926 (10) | 0.0597 (4) | 0.93219 (19) | 0.0596 (8) | |
| O2 | 0.32557 (10) | −0.0581 (4) | 0.9110 (2) | 0.0643 (9) | |
| O3 | 0.44009 (10) | 0.2276 (4) | 0.8794 (2) | 0.0773 (11) | |
| H3 | 0.4137 | 0.2060 | 0.8893 | 0.116* | |
| S1 | 0.29375 (3) | 0.08000 (14) | 0.89918 (7) | 0.0481 (3) | |
| C1 | 0.29054 (13) | 0.1295 (5) | 0.7887 (3) | 0.0457 (10) | |
| C2 | 0.32787 (15) | 0.1092 (6) | 0.7367 (3) | 0.0602 (12) | |
| H2 | 0.3547 | 0.0683 | 0.7601 | 0.072* | |
| C3 | 0.32493 (18) | 0.1505 (7) | 0.6499 (3) | 0.0727 (14) | |
| H3A | 0.3498 | 0.1363 | 0.6142 | 0.087* | |
| C4 | 0.28604 (19) | 0.2114 (7) | 0.6164 (3) | 0.0700 (14) | |
| H4 | 0.2846 | 0.2396 | 0.5578 | 0.084* | |
| C5 | 0.24886 (19) | 0.2323 (7) | 0.6664 (3) | 0.0693 (14) | |
| H5 | 0.2224 | 0.2744 | 0.6420 | 0.083* | |
| C6 | 0.25055 (15) | 0.1908 (6) | 0.7535 (3) | 0.0586 (12) | |
| H6 | 0.2253 | 0.2037 | 0.7882 | 0.070* | |
| C7 | 0.36859 (14) | 0.4638 (6) | 0.9325 (3) | 0.0517 (11) | |
| H7 | 0.3473 | 0.5476 | 0.9489 | 0.062* | |
| C8 | 0.41362 (13) | 0.5202 (6) | 0.9160 (3) | 0.0545 (11) | |
| C9 | 0.44774 (14) | 0.4048 (6) | 0.8899 (3) | 0.0572 (12) | |
| C10 | 0.49056 (14) | 0.4634 (6) | 0.8754 (3) | 0.0630 (13) | |
| H10 | 0.5124 | 0.3820 | 0.8588 | 0.076* | |
| C11 | 0.50227 (15) | 0.6425 (6) | 0.8849 (3) | 0.0661 (13) | |
| C12 | 0.46791 (15) | 0.7606 (7) | 0.9108 (4) | 0.0725 (15) | |
| H12 | 0.4742 | 0.8809 | 0.9179 | 0.087* | |
| C13 | 0.42560 (15) | 0.6996 (6) | 0.9256 (3) | 0.0670 (14) | |
| H13 | 0.4038 | 0.7804 | 0.9427 | 0.080* | |
| C14 | 0.5780 (8) | 0.571 (4) | 0.8341 (15) | 0.095 (6) | 0.84 (2) |
| H14A | 0.5787 | 0.4677 | 0.8715 | 0.114* | 0.84 (2) |
| H14B | 0.5666 | 0.5327 | 0.7784 | 0.114* | 0.84 (2) |
| C15 | 0.6231 (3) | 0.6286 (18) | 0.8217 (10) | 0.114 (4) | 0.84 (2) |
| H15A | 0.6242 | 0.7137 | 0.7754 | 0.171* | 0.84 (2) |
| H15B | 0.6414 | 0.5280 | 0.8074 | 0.171* | 0.84 (2) |
| H15C | 0.6339 | 0.6826 | 0.8740 | 0.171* | 0.84 (2) |
| C16 | 0.5597 (2) | 0.8789 (15) | 0.8999 (8) | 0.076 (3) | 0.84 (2) |
| H16A | 0.5912 | 0.8770 | 0.9147 | 0.092* | 0.84 (2) |
| H16B | 0.5430 | 0.9123 | 0.9513 | 0.092* | 0.84 (2) |
| C17 | 0.5517 (3) | 1.012 (2) | 0.8301 (10) | 0.107 (4) | 0.84 (2) |
| H17A | 0.5649 | 0.9712 | 0.7772 | 0.161* | 0.84 (2) |
| H17B | 0.5650 | 1.1239 | 0.8463 | 0.161* | 0.84 (2) |
| H17C | 0.5201 | 1.0281 | 0.8220 | 0.161* | 0.84 (2) |
| C14' | 0.585 (4) | 0.574 (18) | 0.870 (7) | 0.08 (2) | 0.16 (2) |
| H14C | 0.5748 | 0.4534 | 0.8813 | 0.098* | 0.16 (2) |
| H14D | 0.6063 | 0.6079 | 0.9134 | 0.098* | 0.16 (2) |
| C15' | 0.606 (2) | 0.586 (8) | 0.779 (5) | 0.11 (2) | 0.16 (2) |
| H15D | 0.5939 | 0.6879 | 0.7496 | 0.170* | 0.16 (2) |
| H15E | 0.5985 | 0.4801 | 0.7472 | 0.170* | 0.16 (2) |
| H15F | 0.6375 | 0.5966 | 0.7846 | 0.170* | 0.16 (2) |
| C16' | 0.5486 (13) | 0.875 (8) | 0.826 (4) | 0.082 (18) | 0.16 (2) |
| H16C | 0.5207 | 0.9021 | 0.7969 | 0.099* | 0.16 (2) |
| H16D | 0.5724 | 0.8723 | 0.7830 | 0.099* | 0.16 (2) |
| C17' | 0.5588 (15) | 1.015 (10) | 0.896 (4) | 0.089 (19) | 0.16 (2) |
| H17D | 0.5320 | 1.0407 | 0.9280 | 0.133* | 0.16 (2) |
| H17E | 0.5694 | 1.1224 | 0.8689 | 0.133* | 0.16 (2) |
| H17F | 0.5813 | 0.9706 | 0.9346 | 0.133* | 0.16 (2) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0406 (19) | 0.055 (2) | 0.055 (2) | 0.0017 (16) | −0.0002 (16) | −0.0013 (18) |
| N2 | 0.0378 (18) | 0.057 (2) | 0.059 (2) | 0.0001 (16) | −0.0014 (16) | −0.0042 (18) |
| N3 | 0.053 (2) | 0.065 (3) | 0.120 (4) | −0.008 (2) | 0.015 (2) | −0.019 (3) |
| O1 | 0.0506 (16) | 0.061 (2) | 0.067 (2) | −0.0052 (15) | 0.0125 (15) | −0.0017 (16) |
| O2 | 0.0634 (19) | 0.0535 (19) | 0.076 (2) | 0.0149 (15) | 0.0025 (16) | 0.0112 (17) |
| O3 | 0.0547 (19) | 0.053 (2) | 0.125 (3) | −0.0024 (16) | 0.0098 (19) | −0.022 (2) |
| S1 | 0.0427 (6) | 0.0449 (6) | 0.0566 (7) | 0.0016 (5) | 0.0036 (5) | 0.0027 (5) |
| C1 | 0.044 (2) | 0.038 (2) | 0.054 (3) | 0.0016 (18) | −0.001 (2) | −0.0076 (19) |
| C2 | 0.047 (3) | 0.069 (3) | 0.065 (3) | 0.007 (2) | 0.002 (2) | 0.002 (3) |
| C3 | 0.068 (3) | 0.085 (4) | 0.065 (4) | −0.003 (3) | 0.006 (3) | −0.001 (3) |
| C4 | 0.087 (4) | 0.066 (3) | 0.057 (3) | −0.001 (3) | −0.006 (3) | 0.000 (3) |
| C5 | 0.074 (3) | 0.063 (3) | 0.071 (3) | 0.017 (3) | −0.020 (3) | −0.005 (3) |
| C6 | 0.049 (2) | 0.062 (3) | 0.065 (3) | 0.009 (2) | −0.003 (2) | −0.007 (2) |
| C7 | 0.046 (2) | 0.048 (3) | 0.061 (3) | 0.005 (2) | 0.001 (2) | −0.003 (2) |
| C8 | 0.042 (2) | 0.053 (3) | 0.069 (3) | 0.002 (2) | 0.003 (2) | −0.003 (2) |
| C9 | 0.048 (2) | 0.051 (3) | 0.073 (3) | 0.001 (2) | −0.002 (2) | −0.011 (2) |
| C10 | 0.043 (2) | 0.055 (3) | 0.090 (4) | 0.003 (2) | 0.008 (2) | −0.018 (3) |
| C11 | 0.045 (2) | 0.068 (3) | 0.085 (4) | −0.003 (2) | 0.008 (2) | −0.009 (3) |
| C12 | 0.056 (3) | 0.053 (3) | 0.109 (4) | −0.003 (2) | 0.014 (3) | −0.011 (3) |
| C13 | 0.050 (3) | 0.054 (3) | 0.098 (4) | 0.005 (2) | 0.011 (3) | −0.009 (3) |
| C14 | 0.060 (9) | 0.096 (8) | 0.129 (17) | −0.014 (7) | 0.018 (10) | −0.045 (13) |
| C15 | 0.067 (6) | 0.131 (9) | 0.145 (11) | 0.011 (6) | −0.007 (6) | −0.040 (7) |
| C16 | 0.052 (4) | 0.075 (7) | 0.101 (8) | −0.006 (3) | 0.001 (4) | −0.019 (5) |
| C17 | 0.072 (6) | 0.097 (10) | 0.152 (11) | 0.004 (5) | 0.011 (7) | 0.011 (9) |
| C14' | 0.06 (4) | 0.08 (4) | 0.11 (7) | −0.01 (3) | 0.00 (4) | −0.02 (5) |
| C15' | 0.09 (4) | 0.11 (4) | 0.13 (6) | −0.01 (3) | 0.00 (4) | −0.03 (4) |
| C16' | 0.06 (2) | 0.08 (4) | 0.11 (5) | 0.00 (2) | 0.01 (2) | −0.02 (3) |
| C17' | 0.06 (2) | 0.08 (4) | 0.13 (5) | 0.00 (2) | 0.00 (3) | −0.02 (4) |
| N1—N2 | 1.415 (4) | C10—C11 | 1.398 (6) |
| N1—S1 | 1.642 (4) | C10—H10 | 0.9300 |
| N1—H1 | 0.9000 | C11—C12 | 1.415 (6) |
| N2—C7 | 1.275 (5) | C12—C13 | 1.363 (6) |
| N3—C11 | 1.376 (6) | C12—H12 | 0.9300 |
| N3—C14 | 1.48 (3) | C13—H13 | 0.9300 |
| N3—C16 | 1.485 (11) | C14—C15 | 1.42 (3) |
| N3—C16' | 1.50 (6) | C14—H14A | 0.9700 |
| N3—C14' | 1.50 (15) | C14—H14B | 0.9700 |
| O1—S1 | 1.432 (3) | C15—H15A | 0.9600 |
| O2—S1 | 1.419 (3) | C15—H15B | 0.9600 |
| O3—C9 | 1.361 (5) | C15—H15C | 0.9600 |
| O3—H3 | 0.8200 | C16—C17 | 1.49 (2) |
| S1—C1 | 1.750 (4) | C16—H16A | 0.9700 |
| C1—C2 | 1.382 (6) | C16—H16B | 0.9700 |
| C1—C6 | 1.391 (6) | C17—H17A | 0.9600 |
| C2—C3 | 1.380 (7) | C17—H17B | 0.9600 |
| C2—H2 | 0.9300 | C17—H17C | 0.9600 |
| C3—C4 | 1.351 (7) | C14'—C15' | 1.53 (16) |
| C3—H3A | 0.9300 | C14'—H14C | 0.9700 |
| C4—C5 | 1.362 (7) | C14'—H14D | 0.9700 |
| C4—H4 | 0.9300 | C15'—H15D | 0.9600 |
| C5—C6 | 1.383 (6) | C15'—H15E | 0.9600 |
| C5—H5 | 0.9300 | C15'—H15F | 0.9600 |
| C6—H6 | 0.9300 | C16'—C17' | 1.54 (10) |
| C7—C8 | 1.433 (6) | C16'—H16C | 0.9700 |
| C7—H7 | 0.9300 | C16'—H16D | 0.9700 |
| C8—C9 | 1.398 (6) | C17'—H17D | 0.9600 |
| C8—C13 | 1.403 (6) | C17'—H17E | 0.9600 |
| C9—C10 | 1.371 (6) | C17'—H17F | 0.9600 |
| N2—N1—S1 | 112.9 (3) | C9—C10—C11 | 121.7 (4) |
| N2—N1—H1 | 108.5 | C9—C10—H10 | 119.1 |
| S1—N1—H1 | 108.5 | C11—C10—H10 | 119.1 |
| C7—N2—N1 | 116.9 (4) | N3—C11—C10 | 121.1 (4) |
| C11—N3—C14 | 118.4 (10) | N3—C11—C12 | 122.0 (4) |
| C11—N3—C16 | 120.2 (5) | C10—C11—C12 | 116.9 (4) |
| C14—N3—C16 | 121.2 (10) | C13—C12—C11 | 120.6 (5) |
| C11—N3—C16' | 113.9 (16) | C13—C12—H12 | 119.7 |
| C14—N3—C16' | 111 (2) | C11—C12—H12 | 119.7 |
| C16—N3—C16' | 47 (2) | C12—C13—C8 | 122.8 (4) |
| C11—N3—C14' | 123 (5) | C12—C13—H13 | 118.6 |
| C14—N3—C14' | 23 (4) | C8—C13—H13 | 118.6 |
| C16—N3—C14' | 111 (4) | C15—C14—N3 | 118.4 (18) |
| C16'—N3—C14' | 120 (6) | C15—C14—H14A | 107.7 |
| C9—O3—H3 | 109.5 | N3—C14—H14A | 107.7 |
| O2—S1—O1 | 119.90 (19) | C15—C14—H14B | 107.7 |
| O2—S1—N1 | 107.52 (19) | N3—C14—H14B | 107.7 |
| O1—S1—N1 | 103.83 (18) | H14A—C14—H14B | 107.1 |
| O2—S1—C1 | 108.52 (19) | N3—C16—C17 | 110.4 (12) |
| O1—S1—C1 | 108.61 (19) | N3—C16—H16A | 109.6 |
| N1—S1—C1 | 107.86 (19) | C17—C16—H16A | 109.6 |
| C2—C1—C6 | 120.2 (4) | N3—C16—H16B | 109.6 |
| C2—C1—S1 | 119.9 (3) | C17—C16—H16B | 109.6 |
| C6—C1—S1 | 119.9 (3) | H16A—C16—H16B | 108.1 |
| C3—C2—C1 | 119.2 (4) | N3—C14'—C15' | 107 (8) |
| C3—C2—H2 | 120.4 | N3—C14'—H14C | 110.3 |
| C1—C2—H2 | 120.4 | C15'—C14'—H14C | 110.3 |
| C4—C3—C2 | 120.2 (5) | N3—C14'—H14D | 110.3 |
| C4—C3—H3A | 119.9 | C15'—C14'—H14D | 110.3 |
| C2—C3—H3A | 119.9 | H14C—C14'—H14D | 108.5 |
| C3—C4—C5 | 121.6 (5) | C14'—C15'—H15D | 109.5 |
| C3—C4—H4 | 119.2 | C14'—C15'—H15E | 109.5 |
| C5—C4—H4 | 119.2 | H15D—C15'—H15E | 109.5 |
| C4—C5—C6 | 119.7 (5) | C14'—C15'—H15F | 109.5 |
| C4—C5—H5 | 120.1 | H15D—C15'—H15F | 109.5 |
| C6—C5—H5 | 120.1 | H15E—C15'—H15F | 109.5 |
| C5—C6—C1 | 119.1 (5) | N3—C16'—C17' | 107 (6) |
| C5—C6—H6 | 120.5 | N3—C16'—H16C | 110.4 |
| C1—C6—H6 | 120.5 | C17'—C16'—H16C | 110.4 |
| N2—C7—C8 | 121.4 (4) | N3—C16'—H16D | 110.4 |
| N2—C7—H7 | 119.3 | C17'—C16'—H16D | 110.4 |
| C8—C7—H7 | 119.3 | H16C—C16'—H16D | 108.6 |
| C9—C8—C13 | 116.2 (4) | C16'—C17'—H17D | 109.5 |
| C9—C8—C7 | 123.5 (4) | C16'—C17'—H17E | 109.5 |
| C13—C8—C7 | 120.3 (4) | H17D—C17'—H17E | 109.5 |
| O3—C9—C10 | 116.9 (4) | C16'—C17'—H17F | 109.5 |
| O3—C9—C8 | 121.3 (4) | H17D—C17'—H17F | 109.5 |
| C10—C9—C8 | 121.9 (4) | H17E—C17'—H17F | 109.5 |
| S1—N1—N2—C7 | 153.6 (3) | C16'—N3—C11—C10 | 141 (3) |
| N2—N1—S1—O2 | 52.0 (3) | C14'—N3—C11—C10 | −18 (4) |
| N2—N1—S1—O1 | −179.9 (3) | C14—N3—C11—C12 | −172.9 (12) |
| N2—N1—S1—C1 | −64.8 (3) | C16—N3—C11—C12 | 12.5 (9) |
| O2—S1—C1—C2 | −31.0 (4) | C16'—N3—C11—C12 | −40 (3) |
| O1—S1—C1—C2 | −162.8 (3) | C14'—N3—C11—C12 | 161 (4) |
| N1—S1—C1—C2 | 85.2 (4) | C9—C10—C11—N3 | 179.3 (5) |
| O2—S1—C1—C6 | 149.7 (3) | C9—C10—C11—C12 | 0.4 (8) |
| O1—S1—C1—C6 | 17.8 (4) | N3—C11—C12—C13 | −178.8 (5) |
| N1—S1—C1—C6 | −94.1 (4) | C10—C11—C12—C13 | 0.1 (8) |
| C6—C1—C2—C3 | 0.0 (7) | C11—C12—C13—C8 | −0.2 (9) |
| S1—C1—C2—C3 | −179.4 (4) | C9—C8—C13—C12 | −0.1 (8) |
| C1—C2—C3—C4 | 0.6 (8) | C7—C8—C13—C12 | 179.9 (5) |
| C2—C3—C4—C5 | −0.6 (8) | C11—N3—C14—C15 | −178.5 (15) |
| C3—C4—C5—C6 | 0.0 (8) | C16—N3—C14—C15 | −4(2) |
| C4—C5—C6—C1 | 0.5 (7) | C16'—N3—C14—C15 | 48 (3) |
| C2—C1—C6—C5 | −0.5 (7) | C14'—N3—C14—C15 | −71 (15) |
| S1—C1—C6—C5 | 178.8 (4) | C11—N3—C16—C17 | −89.7 (8) |
| N1—N2—C7—C8 | 175.4 (4) | C14—N3—C16—C17 | 95.8 (13) |
| N2—C7—C8—C9 | 1.0 (7) | C16'—N3—C16—C17 | 6(2) |
| N2—C7—C8—C13 | −179.0 (5) | C14'—N3—C16—C17 | 118 (5) |
| C13—C8—C9—O3 | 179.3 (5) | C11—N3—C14'—C15' | 118 (7) |
| C7—C8—C9—O3 | −0.8 (7) | C14—N3—C14'—C15' | 32 (11) |
| C13—C8—C9—C10 | 0.6 (7) | C16—N3—C14'—C15' | −90 (6) |
| C7—C8—C9—C10 | −179.4 (5) | C16'—N3—C14'—C15' | −39 (8) |
| O3—C9—C10—C11 | −179.5 (5) | C11—N3—C16'—C17' | 101 (3) |
| C8—C9—C10—C11 | −0.8 (8) | C14—N3—C16'—C17' | −123 (2) |
| C14—N3—C11—C10 | 8.3 (13) | C16—N3—C16'—C17' | −9(2) |
| C16—N3—C11—C10 | −166.3 (7) | C14'—N3—C16'—C17' | −100 (4) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···N2 | 0.82 | 1.92 | 2.637 (4) | 146 |
| N1—H1···O1i | 0.90 | 2.06 | 2.944 (5) | 169 |
| Symmetry codes: (i) −x+1/2, y+1/2, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···N2 | 0.82 | 1.92 | 2.637 (4) | 146 |
| N1—H1···O1i | 0.90 | 2.06 | 2.944 (5) | 169 |
| Symmetry codes: (i) −x+1/2, y+1/2, z. |
The authors thank the National Natural Science Foundation of China (20671073), the National Natural Science Foundation of Shandong (Y2007B60), and the Science and Technology Foundation of Weifang and Weifang University for research grants.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Tai, X.-S., Feng, Y.-M. & Kong, F.-Y. (2008). Acta Cryst. E64, o750.
As part of our ongoing studies of aroylhydrazones as potential ligands (Tai et al., 2008), we now report the synthesis and structure of the title compound, (I), (Fig. 1).
The dihedral angle between the aromatic ring planes is 84.2 (2)°. The pendant ethyl groups of the -N(C2H5)2 grouping are disordered over two sets of positions in a 0.84 (2):0.16 (2) ratio. The molecular conformation is stabilised by an intramolecular O-H···N hydrogen bond and intermolecular N-H···O bonds lead to [010] chains in the crystal (Table 1).