organic compounds
4-(Diethylamino)salicylaldehyde phenylsulfonylhydrazone
aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: taixishi@lzu.edu.cn
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—H⋯O bonds lead to [010] chains in the crystal structure.
Experimental
Crystal data
|
Refinement
|
Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; 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.
Supporting information
10.1107/S1600536808010118/hb2720sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010118/hb2720Isup2.hkl
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
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).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 = 2.7–21.4° |
b = 7.5153 (12) Å | µ = 0.21 mm−1 |
c = 15.4456 (19) Å | T = 293 K |
V = 3467.8 (8) Å3 | Plate, colourless |
Z = 8 | 0.43 × 0.38 × 0.04 mm |
F(000) = 1472 |
Bruker SMART CCD diffractometer | 3052 independent reflections |
Radiation source: fine-focus sealed tube | 2061 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ω scans | θmax = 25.0°, θmin = 2.6° |
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 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.175 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0453P)2 + 7.4306P] where P = (Fo2 + 2Fc2)/3 |
3052 reflections | (Δ/σ)max = 0.001 |
258 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C17H21N3O3S | V = 3467.8 (8) Å3 |
Mr = 347.43 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 29.874 (3) Å | µ = 0.21 mm−1 |
b = 7.5153 (12) Å | T = 293 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 | 0 restraints |
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 |
258 parameters |
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 code: (i) −x+1/2, y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C17H21N3O3S |
Mr | 347.43 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 293 |
a, b, c (Å) | 29.874 (3), 7.5153 (12), 15.4456 (19) |
V (Å3) | 3467.8 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.43 × 0.38 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.916, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16321, 3052, 2061 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.175, 1.08 |
No. of reflections | 3052 |
No. of parameters | 258 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.30 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
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 code: (i) −x+1/2, y+1/2, z. |
Acknowledgements
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.
References
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tai, X.-S., Feng, Y.-M. & Kong, F.-Y. (2008). Acta Cryst. E64, o750. Web of Science CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).