Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053652/sj2389sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053652/sj2389Isup2.hkl |
CCDC reference: 672839
A mixture of 3-aminophenol (1.09 g, 0.01 mol) and 4-(diethylamino)-2-hydroxybenzaldehyde (1.92 g, 0.01 mol) in 25 ml of absolute ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 4 h (Fig. 3). On cooling, the solid separated was filtered and recrystallized from acetone (m.p.: 467–473 K). The expected product was 5-(diethylamino)-2-{(E)-[(3-hydroxyphenyl)imino]methyl}phenol, but the structure observed is that of its tautomeric form, (6Z)-3-(diethylamino)-6-{[(3-hydroxyphenyl)amino]methylene}cyclohexa-2,4- dien-1-one. Analysis found: C 70.73, H 7.01, N 9.78%; C17H20N2O2 requires: C 70.81, H 7.09, N 9.85%.
The C14A–C15A ethyl group was disordered over two positions A and B and the occupancy factors refined to 0.766 (8) and 0.234 (8); the two components were constrained to have similar metrical parameters. Owing to the poor diffraction qualities of the crystal, the ratio of observed to unique reflelctions is low (38%).
All H atoms were placed in calculated positions except H1A and H1B which were found in a difference map. All H atoms were refined using a riding model with O—H = 0.82 Å, N—H = 0.86 Å and C—H = 0.93 to 0.97 Å, and with Uiso(H) = 1.0–1.5Ueq(C,O,N).
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C17H20N2O2 | F(000) = 608 |
Mr = 284.35 | Dx = 1.266 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yab | Cell parameters from 3116 reflections |
a = 7.4780 (6) Å | θ = 4.8–32.5° |
b = 15.822 (2) Å | µ = 0.08 mm−1 |
c = 12.6372 (13) Å | T = 296 K |
β = 94.149 (9)° | Chunk, pale yellow |
V = 1491.3 (3) Å3 | 0.55 × 0.43 × 0.27 mm |
Z = 4 |
Oxford Diffraction Gemini diffractometer | 4836 independent reflections |
Radiation source: fine-focus sealed tube | 1828 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.6°, θmin = 4.8° |
ϕ and ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −22→22 |
Tmin = 0.827, Tmax = 1.000 | l = −19→19 |
13075 measured reflections |
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)] = 0.083 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.270 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1294P)2] where P = (Fo2 + 2Fc2)/3 |
4836 reflections | (Δ/σ)max = 0.004 |
201 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C17H20N2O2 | V = 1491.3 (3) Å3 |
Mr = 284.35 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 7.4780 (6) Å | µ = 0.08 mm−1 |
b = 15.822 (2) Å | T = 296 K |
c = 12.6372 (13) Å | 0.55 × 0.43 × 0.27 mm |
β = 94.149 (9)° |
Oxford Diffraction Gemini diffractometer | 4836 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 1828 reflections with I > 2σ(I) |
Tmin = 0.827, Tmax = 1.000 | Rint = 0.058 |
13075 measured reflections |
R[F2 > 2σ(F2)] = 0.083 | 0 restraints |
wR(F2) = 0.270 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.37 e Å−3 |
4836 reflections | Δρmin = −0.19 e Å−3 |
201 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) | |
O1 | −0.7397 (2) | 0.07199 (13) | 1.24994 (15) | 0.0716 (6) | |
H1B | −0.7597 | 0.0388 | 1.2007 | 0.107* | |
O2 | −0.17605 (19) | 0.04039 (11) | 0.89295 (12) | 0.0577 (5) | |
N1 | −0.1930 (2) | 0.10814 (12) | 1.07924 (14) | 0.0480 (5) | |
H1A | −0.2386 | 0.0746 | 1.0310 | 0.058* | |
N2 | 0.3053 (3) | 0.11735 (17) | 0.68516 (17) | 0.0750 (7) | |
C1 | −0.5685 (3) | 0.09987 (15) | 1.25042 (18) | 0.0511 (6) | |
C2 | −0.4974 (3) | 0.14220 (17) | 1.3390 (2) | 0.0617 (7) | |
H2A | −0.5665 | 0.1500 | 1.3965 | 0.074* | |
C3 | −0.3255 (3) | 0.17289 (19) | 1.3430 (2) | 0.0713 (8) | |
H3A | −0.2794 | 0.2013 | 1.4034 | 0.086* | |
C4 | −0.2198 (3) | 0.16219 (19) | 1.2589 (2) | 0.0655 (7) | |
H4A | −0.1033 | 0.1831 | 1.2620 | 0.079* | |
C5 | −0.2913 (3) | 0.11953 (14) | 1.16938 (17) | 0.0451 (5) | |
C6 | −0.4639 (3) | 0.08804 (14) | 1.16547 (17) | 0.0474 (6) | |
H6A | −0.5101 | 0.0589 | 1.1057 | 0.057* | |
C7 | −0.0377 (3) | 0.14383 (15) | 1.06111 (18) | 0.0496 (6) | |
H7A | 0.0181 | 0.1776 | 1.1139 | 0.060* | |
C8 | 0.0459 (3) | 0.13346 (14) | 0.96764 (17) | 0.0456 (5) | |
C9 | 0.2103 (3) | 0.17529 (17) | 0.9547 (2) | 0.0616 (7) | |
H9A | 0.2616 | 0.2076 | 1.0104 | 0.074* | |
C10 | 0.2951 (3) | 0.16995 (19) | 0.8644 (2) | 0.0684 (8) | |
H10A | 0.4025 | 0.1987 | 0.8589 | 0.082* | |
C11 | 0.2219 (3) | 0.12066 (16) | 0.77704 (18) | 0.0533 (6) | |
C12 | 0.0630 (3) | 0.07688 (15) | 0.78963 (17) | 0.0499 (6) | |
H12A | 0.0153 | 0.0433 | 0.7341 | 0.060* | |
C13 | −0.0277 (3) | 0.08148 (14) | 0.88289 (17) | 0.0451 (5) | |
C14A | 0.4495 (4) | 0.1786 (2) | 0.6598 (3) | 0.0623 (12) | 0.766 (8) |
H14A | 0.4271 | 0.1989 | 0.5876 | 0.075* | 0.766 (8) |
H14B | 0.4483 | 0.2268 | 0.7072 | 0.075* | 0.766 (8) |
C15A | 0.6271 (5) | 0.1367 (4) | 0.6718 (4) | 0.1014 (19) | 0.766 (8) |
H15A | 0.7188 | 0.1767 | 0.6574 | 0.152* | 0.766 (8) |
H15B | 0.6294 | 0.0905 | 0.6228 | 0.152* | 0.766 (8) |
H15C | 0.6480 | 0.1159 | 0.7430 | 0.152* | 0.766 (8) |
C14B | 0.5209 (15) | 0.1174 (9) | 0.6931 (10) | 0.0623 (12) | 0.234 (8) |
H14C | 0.5708 | 0.1167 | 0.7661 | 0.075* | 0.234 (8) |
H14D | 0.5689 | 0.0704 | 0.6548 | 0.075* | 0.234 (8) |
C15B | 0.5501 (19) | 0.1965 (12) | 0.6427 (15) | 0.1014 (19) | 0.234 (8) |
H15D | 0.6761 | 0.2040 | 0.6356 | 0.152* | 0.234 (8) |
H15E | 0.5066 | 0.2415 | 0.6848 | 0.152* | 0.234 (8) |
H15F | 0.4873 | 0.1971 | 0.5737 | 0.152* | 0.234 (8) |
C16 | 0.2402 (3) | 0.06431 (19) | 0.5966 (2) | 0.0686 (8) | |
H16A | 0.1915 | 0.0126 | 0.6240 | 0.082* | |
H16B | 0.3401 | 0.0492 | 0.5556 | 0.082* | |
C17 | 0.0984 (4) | 0.1068 (2) | 0.5251 (2) | 0.0825 (9) | |
H17A | 0.0794 | 0.0752 | 0.4604 | 0.124* | |
H17B | 0.1366 | 0.1631 | 0.5092 | 0.124* | |
H17C | −0.0114 | 0.1094 | 0.5599 | 0.124* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0535 (10) | 0.0900 (15) | 0.0739 (12) | −0.0143 (9) | 0.0228 (8) | −0.0231 (10) |
O2 | 0.0493 (9) | 0.0725 (12) | 0.0530 (9) | −0.0226 (8) | 0.0151 (7) | −0.0032 (8) |
N1 | 0.0441 (9) | 0.0575 (12) | 0.0431 (10) | −0.0080 (9) | 0.0086 (7) | −0.0054 (9) |
N2 | 0.0532 (11) | 0.1144 (19) | 0.0599 (13) | −0.0330 (12) | 0.0211 (9) | −0.0154 (13) |
C1 | 0.0454 (12) | 0.0495 (14) | 0.0588 (14) | −0.0043 (10) | 0.0067 (10) | −0.0068 (11) |
C2 | 0.0662 (16) | 0.0635 (17) | 0.0575 (14) | 0.0039 (13) | 0.0194 (12) | −0.0164 (13) |
C3 | 0.0636 (16) | 0.091 (2) | 0.0596 (15) | −0.0096 (14) | 0.0055 (12) | −0.0296 (15) |
C4 | 0.0516 (13) | 0.0794 (19) | 0.0659 (15) | −0.0145 (13) | 0.0072 (11) | −0.0186 (14) |
C5 | 0.0497 (11) | 0.0401 (12) | 0.0461 (11) | −0.0013 (10) | 0.0069 (9) | −0.0014 (10) |
C6 | 0.0493 (11) | 0.0503 (13) | 0.0436 (11) | −0.0060 (10) | 0.0110 (9) | −0.0108 (10) |
C7 | 0.0440 (12) | 0.0531 (14) | 0.0511 (12) | −0.0028 (10) | 0.0000 (9) | 0.0023 (11) |
C8 | 0.0378 (10) | 0.0518 (13) | 0.0474 (12) | −0.0039 (10) | 0.0053 (9) | 0.0050 (10) |
C9 | 0.0496 (13) | 0.0783 (18) | 0.0561 (14) | −0.0193 (13) | −0.0019 (11) | −0.0089 (13) |
C10 | 0.0446 (12) | 0.093 (2) | 0.0675 (16) | −0.0293 (13) | 0.0037 (11) | 0.0005 (15) |
C11 | 0.0409 (11) | 0.0651 (16) | 0.0542 (13) | −0.0123 (11) | 0.0059 (9) | 0.0013 (12) |
C12 | 0.0433 (11) | 0.0593 (15) | 0.0477 (12) | −0.0139 (10) | 0.0079 (9) | −0.0013 (11) |
C13 | 0.0366 (10) | 0.0475 (13) | 0.0513 (12) | −0.0020 (9) | 0.0048 (9) | 0.0075 (10) |
C14A | 0.046 (2) | 0.075 (3) | 0.068 (2) | −0.0068 (16) | 0.0144 (15) | 0.0042 (17) |
C15A | 0.037 (2) | 0.122 (4) | 0.145 (4) | −0.001 (2) | 0.008 (2) | 0.017 (3) |
C14B | 0.046 (2) | 0.075 (3) | 0.068 (2) | −0.0068 (16) | 0.0144 (15) | 0.0042 (17) |
C15B | 0.037 (2) | 0.122 (4) | 0.145 (4) | −0.001 (2) | 0.008 (2) | 0.017 (3) |
C16 | 0.0639 (15) | 0.077 (2) | 0.0674 (17) | −0.0133 (14) | 0.0226 (13) | −0.0083 (15) |
C17 | 0.0799 (19) | 0.095 (2) | 0.0738 (19) | −0.0132 (17) | 0.0118 (15) | −0.0002 (17) |
O1—C1 | 1.353 (3) | C9—H9A | 0.9300 |
O1—H1B | 0.8200 | C10—C11 | 1.428 (3) |
O2—C13 | 1.300 (2) | C10—H10A | 0.9300 |
N1—C7 | 1.326 (3) | C11—C12 | 1.394 (3) |
N1—C5 | 1.411 (3) | C12—C13 | 1.404 (3) |
N1—H1A | 0.8600 | C12—H12A | 0.9300 |
N2—C11 | 1.358 (3) | C14A—C15A | 1.482 (5) |
N2—C16 | 1.454 (3) | C14A—H14A | 0.9700 |
N2—C14A | 1.502 (4) | C14A—H14B | 0.9700 |
N2—C14B | 1.609 (11) | C15A—H15A | 0.9600 |
C1—C2 | 1.378 (3) | C15A—H15B | 0.9600 |
C1—C6 | 1.386 (3) | C15A—H15C | 0.9600 |
C2—C3 | 1.372 (3) | C14B—C15B | 1.43 (2) |
C2—H2A | 0.9300 | C14B—H14C | 0.9700 |
C3—C4 | 1.381 (3) | C14B—H14D | 0.9700 |
C3—H3A | 0.9300 | C15B—H15D | 0.9600 |
C4—C5 | 1.390 (3) | C15B—H15E | 0.9600 |
C4—H4A | 0.9300 | C15B—H15F | 0.9600 |
C5—C6 | 1.382 (3) | C16—C17 | 1.502 (4) |
C6—H6A | 0.9300 | C16—H16A | 0.9700 |
C7—C8 | 1.386 (3) | C16—H16B | 0.9700 |
C7—H7A | 0.9300 | C17—H17A | 0.9600 |
C8—C9 | 1.416 (3) | C17—H17B | 0.9600 |
C8—C13 | 1.429 (3) | C17—H17C | 0.9600 |
C9—C10 | 1.347 (3) | ||
C1—O1—H1B | 109.5 | N2—C11—C12 | 121.7 (2) |
C7—N1—C5 | 126.78 (19) | N2—C11—C10 | 120.52 (19) |
C7—N1—H1A | 116.6 | C12—C11—C10 | 117.7 (2) |
C5—N1—H1A | 116.6 | C11—C12—C13 | 122.5 (2) |
C11—N2—C16 | 122.10 (19) | C11—C12—H12A | 118.7 |
C11—N2—C14A | 122.6 (2) | C13—C12—H12A | 118.7 |
C16—N2—C14A | 114.5 (2) | O2—C13—C12 | 121.6 (2) |
C11—N2—C14B | 117.8 (5) | O2—C13—C8 | 120.00 (19) |
C16—N2—C14B | 109.1 (5) | C12—C13—C8 | 118.40 (18) |
O1—C1—C2 | 118.1 (2) | C15A—C14A—N2 | 109.9 (3) |
O1—C1—C6 | 122.6 (2) | C15A—C14A—H14A | 109.7 |
C2—C1—C6 | 119.3 (2) | N2—C14A—H14A | 109.7 |
C3—C2—C1 | 120.5 (2) | C15A—C14A—H14B | 109.7 |
C3—C2—H2A | 119.7 | N2—C14A—H14B | 109.7 |
C1—C2—H2A | 119.7 | H14A—C14A—H14B | 108.2 |
C2—C3—C4 | 121.0 (2) | C15B—C14B—N2 | 99.1 (10) |
C2—C3—H3A | 119.5 | C15B—C14B—H14C | 112.0 |
C4—C3—H3A | 119.5 | N2—C14B—H14C | 112.0 |
C3—C4—C5 | 118.6 (2) | C15B—C14B—H14D | 112.0 |
C3—C4—H4A | 120.7 | N2—C14B—H14D | 112.0 |
C5—C4—H4A | 120.7 | H14C—C14B—H14D | 109.6 |
C6—C5—C4 | 120.49 (19) | C14B—C15B—H15D | 109.5 |
C6—C5—N1 | 117.71 (18) | C14B—C15B—H15E | 109.5 |
C4—C5—N1 | 121.78 (19) | H15D—C15B—H15E | 109.5 |
C5—C6—C1 | 120.1 (2) | C14B—C15B—H15F | 109.5 |
C5—C6—H6A | 119.9 | H15D—C15B—H15F | 109.5 |
C1—C6—H6A | 119.9 | H15E—C15B—H15F | 109.5 |
N1—C7—C8 | 123.5 (2) | N2—C16—C17 | 112.8 (2) |
N1—C7—H7A | 118.3 | N2—C16—H16A | 109.0 |
C8—C7—H7A | 118.3 | C17—C16—H16A | 109.0 |
C7—C8—C9 | 119.5 (2) | N2—C16—H16B | 109.0 |
C7—C8—C13 | 122.26 (19) | C17—C16—H16B | 109.0 |
C9—C8—C13 | 118.24 (19) | H16A—C16—H16B | 107.8 |
C10—C9—C8 | 122.3 (2) | C16—C17—H17A | 109.5 |
C10—C9—H9A | 118.9 | C16—C17—H17B | 109.5 |
C8—C9—H9A | 118.9 | H17A—C17—H17B | 109.5 |
C9—C10—C11 | 120.7 (2) | C16—C17—H17C | 109.5 |
C9—C10—H10A | 119.6 | H17A—C17—H17C | 109.5 |
C11—C10—H10A | 119.6 | H17B—C17—H17C | 109.5 |
O1—C1—C2—C3 | −179.0 (2) | C14A—N2—C11—C10 | −14.6 (4) |
C6—C1—C2—C3 | 0.4 (4) | C14B—N2—C11—C10 | 36.5 (7) |
C1—C2—C3—C4 | 0.0 (4) | C9—C10—C11—N2 | 178.2 (3) |
C2—C3—C4—C5 | 0.0 (4) | C9—C10—C11—C12 | −1.6 (4) |
C3—C4—C5—C6 | −0.5 (4) | N2—C11—C12—C13 | −178.1 (2) |
C3—C4—C5—N1 | 178.3 (2) | C10—C11—C12—C13 | 1.6 (4) |
C7—N1—C5—C6 | 169.4 (2) | C11—C12—C13—O2 | 179.8 (2) |
C7—N1—C5—C4 | −9.5 (4) | C11—C12—C13—C8 | 0.3 (3) |
C4—C5—C6—C1 | 1.0 (4) | C7—C8—C13—O2 | −1.6 (3) |
N1—C5—C6—C1 | −177.9 (2) | C9—C8—C13—O2 | 178.3 (2) |
O1—C1—C6—C5 | 178.5 (2) | C7—C8—C13—C12 | 177.9 (2) |
C2—C1—C6—C5 | −0.9 (4) | C9—C8—C13—C12 | −2.3 (3) |
C5—N1—C7—C8 | −176.0 (2) | C11—N2—C14A—C15A | 105.3 (4) |
N1—C7—C8—C9 | 178.9 (2) | C16—N2—C14A—C15A | −85.1 (4) |
N1—C7—C8—C13 | −1.3 (3) | C14B—N2—C14A—C15A | 7.5 (7) |
C7—C8—C9—C10 | −177.8 (3) | C11—N2—C14B—C15B | −115.0 (10) |
C13—C8—C9—C10 | 2.4 (4) | C16—N2—C14B—C15B | 100.1 (10) |
C8—C9—C10—C11 | −0.4 (4) | C14A—N2—C14B—C15B | −5.7 (8) |
C16—N2—C11—C12 | −3.6 (4) | C11—N2—C16—C17 | 85.9 (3) |
C14A—N2—C11—C12 | 165.2 (3) | C14A—N2—C16—C17 | −83.8 (3) |
C14B—N2—C11—C12 | −143.7 (6) | C14B—N2—C16—C17 | −131.0 (5) |
C16—N2—C11—C10 | 176.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O2i | 0.82 | 1.77 | 2.580 (2) | 172 |
N1—H1A···O2 | 0.86 | 1.92 | 2.598 (2) | 135 |
C15A—H15C···O2ii | 0.96 | 2.53 | 3.422 (5) | 155 |
Symmetry codes: (i) −x−1, −y, −z+2; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C17H20N2O2 |
Mr | 284.35 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 296 |
a, b, c (Å) | 7.4780 (6), 15.822 (2), 12.6372 (13) |
β (°) | 94.149 (9) |
V (Å3) | 1491.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.55 × 0.43 × 0.27 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.827, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13075, 4836, 1828 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.758 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.083, 0.270, 1.02 |
No. of reflections | 4836 |
No. of parameters | 201 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.19 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O2i | 0.82 | 1.77 | 2.580 (2) | 171.6 |
N1—H1A···O2 | 0.86 | 1.92 | 2.598 (2) | 135.1 |
C15A—H15C···O2ii | 0.96 | 2.53 | 3.422 (5) | 154.8 |
Symmetry codes: (i) −x−1, −y, −z+2; (ii) x+1, y, z. |
Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Some Schiff base derivatives are also known to have biological activities such as antimicrobial (El-Masry et al. 2000; Pandey et al. 1999); antifungal (Singh & Dash 1988; Varma et al. 1986); antitumor (Hodnett & Dunn 1970; Misra et al. 1981; Agarwal et al. 1983) and as herbicides (Samadhiya & Halve, 2001). The crystal structures of (E)-2-hydroxy-5-methyl-3-[(4-methyl-2 pyridyl)iminomethyl] benzaldehyde (Büyükgüngör, et al. 2007); (E)-2-hydroxy-5-methyl-3-[(2-pyridylimino) methyl]benzaldehyde (Odabaşoğlu, et al. 2007); 1-(4-{[(E)-(4-diethylamino-2-hydroxy phenyl)methylene]amino}phenyl)ethanone (Yathirajan et al. 2007) and 2-{(E)-[(2-chloro-5-nitrophenyl)imino]methyl}-5-(diethylamino)phenol (Butcher et al. 2007); 6(Z)-((2-hydroxyphenylamino)methylene)-3-(diethylamino)cyclohexyl-2,4-dien-1-one (Bohme & Fels, 2006) and N-(2-hydroxybenzylidene)-4-diethylamino-2-hydroxyaniline (Nagao et al. 2002) have been reported previously. The title compound (6Z)-3-(diethylamino)-6-{[(3-hydroxyphenyl)amino]methylene} cyclohexa-2,4-dien-1-one, (I), C17H20N2O2 was the unexpected product of an attempt to synthesize a new Schiff base, 5-(diethylamino)-2-{(E)-[(3-hydroxyphenyl)imino]methyl}phenol by enolization and its crystal structure is reported here.
The angle between the mean planes of the planar 3-hydroxyphenyl and cyclohexa-2,4-dien-1-one groups of the title molecule is 10.7 (7)° Fig. 1). These two rings are twisted slightly about the methylene amino group with torsion angles of -9.5 (4) [C7—N1—C5—C4] and 178.9 (2) [N1—C7—C8—C9], respectively. Intramolecular N1—H1A···O2 hydrogen bonding contributes to the overall planarity of the molecule. One of the ethyl arms is disordered over two conformations which are constrained to have similar metrical parameters with occupancies of 0.234 (8) [C14A] and 0.766 (8) [C15A] respectively. Crystal packing is stabilized by intermolecular C15A—H1A···O2 and O1—H1B···O2 hydrogen bonds (Fig 2) that link the molecules into chains in an alternate inverted pattern, which is parallel and oblique to the bc face and diagonal to the a axis of the unit cell (Fig. 2).