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In the title compound, C20H22N2O, the indole and hexylphenyl groups are connected by a C-N bond of 1.431 (2) Å. The molecule is not planar.
Supporting information
CCDC reference: 209990
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.050
- wR factor = 0.132
- Data-to-parameter ratio = 12.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_369 Alert C Long C(sp2)-C(sp2) Bond C(1) - C(2) = 1.53 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
All chemicals used were at analytical purity, namely isatin, 4-butylaniline, phosphorus pentoxide. Ethanol and methanol was distilled and dried prior to use according to methods reported in the literature. The carbon, hydrogen, and nitrogen microanalyses were carried on a Carlo Erba 1106 elemental analyser. The Fourier transformation IR spectra (FT–IR) were recorded with Unicam Mattson 1000 F T–IR spectrophotometer (in the range 400–4000 cm−1), using KBr pellet (1 mg per 100 mg) technique. The electronic spectra were recorded on a Philips PU 8700 spectrophotometer (in the region 190–700 nm) using 10−3 mol dm−3 solution in DMF and ethanol. 1H NMR data were recorded on Bruker AC 200 L. The free ligand, Schiff base, was sythesized by usual condensation reaction. The preparation of the Schiff base was conducted as follows: an ethanol solution of isatin (0.001 mol per 25 ml) was added to an ethanol solution of 4-hexylaniline (0.001 mol per 25 ml) and refluxed for 4 h on a water bath. After solution concentration, the precipitate was separated by suction filtration, washed with ethanol and dried over P2O5 in vacuum. The orange product was recrystallized from methanol. Colours, yields, melting point, and analytical data are as follows: C20H22N2O, orange, yield 75–80%, m.p. 456 K. Analysis calculated: C 78.30, H 6.98, N 9.20%; found: C 78.43, H 7.19, N 9.15%. λmax (DMF, nm): 328 440 The IR spectral data of the title compound [frequency (cm−1), KBr]: 3182 (NH), 2927–2851 (Ar—H3), 1753 (C═O), 1651 (C═N), 1600 (C═C). 1H NMR (D2O, d, p.p.m.) spectral data of the title compound: 0.85 (m, 3H, CH3), 1.23 (s, 6H, –CH2–), 1.62 (m, 2H, –CH2–), 2.6 (m, 2H, –CH2), 6.42–6.65 (two symmetric m, 2H, Ar–H), 7.00–7.40 (two m, 4H, Ar—H), 10.98 (s, 1H, NH).
All H atoms were located geometrically and their coordinates refined isotropically.
Data collection: COLLECT (Nonius, 1999); cell refinement: EVALCCD (Duisenberg, 1998); data reduction: EVALCCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C20H22N2O | F(000) = 656 |
Mr = 306.40 | Dx = 1.198 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 155 reflections |
a = 17.1506 (2) Å | θ = 6.0–20.0° |
b = 9.6464 (2) Å | µ = 0.07 mm−1 |
c = 10.4167 (2) Å | T = 294 K |
β = 99.693 (2)° | Plate, orange |
V = 1698.75 (5) Å3 | 0.52 × 0.31 × 0.05 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 2121 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.089 |
Graphite monochromator | θmax = 26.0°, θmin = 3.6° |
Detector resolution: 9 pixels mm-1 | h = −21→21 |
ϕ– and ω–scans with 2.0 ° and 120 second per frame | k = −11→11 |
30666 measured reflections | l = −12→12 |
3326 independent reflections | |
Refinement top
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | Only H-atom coordinates refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0575P)2 + 0.3745P] where P = (Fo2 + 2Fc2)/3 |
3326 reflections | (Δ/σ)max < 0.001 |
274 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Crystal data top
C20H22N2O | V = 1698.75 (5) Å3 |
Mr = 306.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.1506 (2) Å | µ = 0.07 mm−1 |
b = 9.6464 (2) Å | T = 294 K |
c = 10.4167 (2) Å | 0.52 × 0.31 × 0.05 mm |
β = 99.693 (2)° | |
Data collection top
Nonius KappaCCD diffractometer | 2121 reflections with I > 2σ(I) |
30666 measured reflections | Rint = 0.089 |
3326 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.132 | Only H-atom coordinates refined |
S = 1.05 | Δρmax = 0.14 e Å−3 |
3326 reflections | Δρmin = −0.18 e Å−3 |
274 parameters | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.00779 (9) | 0.45436 (15) | −0.33365 (15) | 0.0620 (6) | |
N1 | 0.01978 (9) | 0.61028 (17) | −0.16356 (17) | 0.0466 (6) | |
N2 | 0.11124 (9) | 0.28834 (16) | −0.18012 (16) | 0.0473 (6) | |
C1 | 0.02712 (11) | 0.4898 (2) | −0.2277 (2) | 0.0439 (7) | |
C2 | 0.09157 (10) | 0.40710 (19) | −0.14094 (18) | 0.0400 (6) | |
C3 | 0.11827 (10) | 0.49415 (18) | −0.02711 (18) | 0.0384 (6) | |
C4 | 0.07286 (10) | 0.61641 (19) | −0.04482 (19) | 0.0410 (6) | |
C5 | 0.08244 (13) | 0.7210 (2) | 0.0463 (2) | 0.0520 (8) | |
C6 | 0.13775 (13) | 0.7005 (2) | 0.1585 (2) | 0.0539 (8) | |
C7 | 0.18189 (13) | 0.5795 (2) | 0.1796 (2) | 0.0515 (7) | |
C8 | 0.17223 (11) | 0.4752 (2) | 0.0866 (2) | 0.0460 (7) | |
C9 | 0.17748 (11) | 0.21715 (18) | −0.10721 (18) | 0.0424 (6) | |
C10 | 0.25233 (12) | 0.2453 (2) | −0.1352 (2) | 0.0529 (7) | |
C11 | 0.31742 (13) | 0.1745 (2) | −0.0713 (2) | 0.0542 (8) | |
C12 | 0.31026 (12) | 0.07424 (19) | 0.0215 (2) | 0.0468 (7) | |
C13 | 0.23480 (12) | 0.0461 (2) | 0.0461 (2) | 0.0507 (7) | |
C14 | 0.16877 (12) | 0.1156 (2) | −0.0174 (2) | 0.0504 (7) | |
C15 | 0.38268 (14) | 0.0019 (2) | 0.0943 (3) | 0.0582 (8) | |
C16 | 0.43551 (14) | 0.0953 (2) | 0.1882 (3) | 0.0631 (9) | |
C17 | 0.50672 (14) | 0.0243 (3) | 0.2667 (3) | 0.0615 (9) | |
C18 | 0.55691 (15) | 0.1160 (3) | 0.3641 (3) | 0.0691 (9) | |
C19 | 0.62297 (16) | 0.0458 (3) | 0.4525 (3) | 0.0746 (10) | |
C20 | 0.67233 (18) | 0.1385 (4) | 0.5500 (3) | 0.0807 (11) | |
H1 | −0.0165 (15) | 0.672 (3) | −0.193 (2) | 0.0800* | |
H5 | 0.0509 (14) | 0.804 (3) | 0.034 (2) | 0.0800* | |
H6 | 0.1463 (14) | 0.775 (3) | 0.226 (2) | 0.0800* | |
H7 | 0.2209 (14) | 0.568 (2) | 0.262 (2) | 0.0800* | |
H8 | 0.2037 (14) | 0.393 (3) | 0.102 (2) | 0.0800* | |
H10 | 0.2591 (14) | 0.312 (3) | −0.198 (2) | 0.0800* | |
H11 | 0.3712 (15) | 0.194 (2) | −0.096 (2) | 0.0800* | |
H13 | 0.2271 (14) | −0.023 (3) | 0.110 (2) | 0.0800* | |
H14 | 0.1163 (15) | 0.095 (2) | −0.002 (2) | 0.0800* | |
H15A | 0.3649 (14) | −0.075 (3) | 0.143 (2) | 0.0800* | |
H15B | 0.4138 (14) | −0.040 (3) | 0.030 (2) | 0.0800* | |
H16A | 0.4542 (14) | 0.171 (3) | 0.141 (2) | 0.0800* | |
H16B | 0.4028 (14) | 0.139 (3) | 0.250 (2) | 0.0800* | |
H17A | 0.4876 (14) | −0.054 (3) | 0.314 (2) | 0.0800* | |
H17B | 0.5355 (15) | −0.025 (3) | 0.213 (3) | 0.0800* | |
H18A | 0.5811 (14) | 0.185 (3) | 0.310 (2) | 0.0800* | |
H18B | 0.5261 (15) | 0.166 (3) | 0.413 (2) | 0.0800* | |
H19A | 0.6549 (15) | −0.004 (3) | 0.400 (2) | 0.0800* | |
H19B | 0.5964 (14) | −0.031 (3) | 0.496 (2) | 0.0800* | |
H20A | 0.6414 (15) | 0.189 (3) | 0.602 (2) | 0.0800* | |
H20B | 0.7142 (15) | 0.084 (3) | 0.613 (2) | 0.0800* | |
H20C | 0.7006 (14) | 0.211 (3) | 0.500 (2) | 0.0800* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0568 (9) | 0.0638 (10) | 0.0562 (10) | 0.0018 (7) | −0.0170 (8) | 0.0027 (8) |
N1 | 0.0405 (9) | 0.0429 (10) | 0.0534 (11) | 0.0068 (7) | −0.0008 (8) | 0.0087 (8) |
N2 | 0.0433 (9) | 0.0434 (10) | 0.0502 (10) | 0.0000 (8) | −0.0062 (8) | −0.0018 (8) |
C1 | 0.0363 (10) | 0.0447 (12) | 0.0480 (12) | −0.0055 (8) | −0.0005 (9) | 0.0080 (10) |
C2 | 0.0343 (9) | 0.0394 (11) | 0.0444 (11) | −0.0031 (8) | 0.0013 (8) | 0.0051 (9) |
C3 | 0.0338 (9) | 0.0385 (10) | 0.0420 (11) | −0.0022 (8) | 0.0034 (8) | 0.0047 (9) |
C4 | 0.0360 (10) | 0.0411 (11) | 0.0455 (12) | −0.0015 (8) | 0.0057 (9) | 0.0081 (9) |
C5 | 0.0540 (13) | 0.0432 (12) | 0.0595 (14) | 0.0053 (10) | 0.0116 (11) | 0.0007 (11) |
C6 | 0.0568 (13) | 0.0522 (13) | 0.0527 (13) | −0.0004 (10) | 0.0093 (11) | −0.0069 (11) |
C7 | 0.0520 (12) | 0.0553 (13) | 0.0448 (13) | −0.0008 (10) | 0.0016 (10) | −0.0005 (10) |
C8 | 0.0412 (11) | 0.0474 (12) | 0.0468 (12) | 0.0012 (9) | −0.0002 (10) | 0.0027 (10) |
C9 | 0.0443 (11) | 0.0331 (10) | 0.0451 (12) | 0.0010 (8) | −0.0061 (9) | −0.0059 (9) |
C10 | 0.0500 (12) | 0.0446 (12) | 0.0614 (14) | −0.0011 (10) | 0.0015 (10) | 0.0087 (10) |
C11 | 0.0432 (12) | 0.0519 (12) | 0.0657 (15) | 0.0023 (10) | 0.0042 (11) | 0.0055 (11) |
C12 | 0.0499 (12) | 0.0347 (10) | 0.0516 (12) | 0.0028 (9) | −0.0037 (10) | −0.0055 (9) |
C13 | 0.0559 (13) | 0.0423 (12) | 0.0499 (13) | −0.0044 (10) | −0.0026 (10) | 0.0045 (10) |
C14 | 0.0451 (12) | 0.0522 (13) | 0.0508 (13) | −0.0046 (10) | −0.0013 (10) | 0.0023 (10) |
C15 | 0.0570 (13) | 0.0448 (12) | 0.0677 (16) | 0.0117 (10) | −0.0044 (12) | 0.0005 (12) |
C16 | 0.0582 (14) | 0.0485 (13) | 0.0741 (17) | 0.0082 (11) | −0.0130 (12) | −0.0014 (12) |
C17 | 0.0513 (13) | 0.0580 (14) | 0.0708 (17) | 0.0096 (11) | −0.0024 (12) | 0.0028 (13) |
C18 | 0.0591 (15) | 0.0583 (15) | 0.0820 (19) | 0.0005 (12) | −0.0107 (13) | 0.0087 (14) |
C19 | 0.0537 (14) | 0.0826 (19) | 0.082 (2) | 0.0088 (13) | −0.0047 (14) | 0.0044 (16) |
C20 | 0.0630 (17) | 0.097 (2) | 0.075 (2) | 0.0033 (15) | −0.0093 (14) | 0.0049 (17) |
Geometric parameters (Å, º) top
O1—C1 | 1.213 (3) | C18—C19 | 1.496 (4) |
N1—C1 | 1.357 (3) | C19—C20 | 1.503 (4) |
N1—C4 | 1.408 (3) | C5—H5 | 0.96 (3) |
N2—C2 | 1.280 (2) | C6—H6 | 1.00 (3) |
N2—C9 | 1.431 (2) | C7—H7 | 1.00 (2) |
N1—H1 | 0.88 (3) | C8—H8 | 0.96 (3) |
C1—C2 | 1.529 (3) | C10—H10 | 0.94 (3) |
C2—C3 | 1.462 (3) | C11—H11 | 1.02 (3) |
C3—C8 | 1.387 (3) | C13—H13 | 0.97 (2) |
C3—C4 | 1.408 (3) | C14—H14 | 0.96 (3) |
C4—C5 | 1.376 (3) | C15—H15A | 0.98 (3) |
C5—C6 | 1.390 (3) | C15—H15B | 1.01 (2) |
C6—C7 | 1.388 (3) | C16—H16A | 0.96 (3) |
C7—C8 | 1.387 (3) | C16—H16B | 1.01 (2) |
C9—C10 | 1.390 (3) | C17—H17A | 0.99 (3) |
C9—C14 | 1.380 (3) | C17—H17B | 0.94 (3) |
C10—C11 | 1.380 (3) | C18—H18A | 1.01 (3) |
C11—C12 | 1.387 (3) | C18—H18B | 0.93 (3) |
C12—C13 | 1.388 (3) | C19—H19A | 0.96 (3) |
C12—C15 | 1.512 (3) | C19—H19B | 1.02 (3) |
C13—C14 | 1.385 (3) | C20—H20A | 0.95 (3) |
C15—C16 | 1.514 (4) | C20—H20B | 1.03 (3) |
C16—C17 | 1.514 (4) | C20—H20C | 1.04 (3) |
C17—C18 | 1.503 (4) | | |
| | | |
O1···N2 | 2.862 (2) | H1···N2ii | 2.22 (3) |
O1···C5i | 3.265 (3) | H1···C2ii | 3.01 (3) |
O1···C14ii | 3.318 (3) | H5···O1ii | 2.55 (2) |
O1···H1i | 2.76 (3) | H6···N1ix | 2.85 (2) |
O1···H5i | 2.55 (2) | H6···C4ix | 3.07 (2) |
O1···H14ii | 2.68 (2) | H8···C9 | 2.74 (2) |
N1···N2ii | 3.069 (2) | H8···C10 | 3.09 (2) |
N2···O1 | 2.862 (2) | H8···C14 | 2.97 (3) |
N2···N1i | 3.069 (2) | H8···C10viii | 3.03 (2) |
N1···H6iii | 2.85 (2) | H10···C13vii | 2.96 (2) |
N2···H1i | 2.22 (2) | H11···H16Bvii | 2.40 (3) |
C1···C5iv | 3.526 (3) | H13···H15A | 2.38 (3) |
C1···C6iv | 3.546 (3) | H14···O1i | 2.68 (2) |
C2···C5iv | 3.521 (3) | H15A···H13 | 2.38 (3) |
C4···C4iv | 3.598 (3) | H15A···H17A | 2.53 (3) |
C5···C2iv | 3.521 (3) | H15A···H18Avi | 2.51 (4) |
C5···O1ii | 3.265 (3) | H15B···H17B | 2.58 (4) |
C5···C1iv | 3.526 (3) | H16A···C11 | 2.94 (2) |
C6···C1iv | 3.546 (3) | H16A···H18A | 2.56 (3) |
C8···C20v | 3.590 (4) | H16B···H18B | 2.49 (3) |
C8···C9 | 3.216 (3) | H16B···H11viii | 2.40 (3) |
C9···C8 | 3.216 (3) | H17A···H15A | 2.53 (3) |
C14···O1i | 3.318 (3) | H17A···H19B | 2.44 (3) |
C20···C8vi | 3.590 (4) | H17B···H15B | 2.58 (4) |
C2···H1i | 3.01 (3) | H17B···H19A | 2.59 (4) |
C4···H6iii | 3.07 (2) | H18A···H16A | 2.56 (3) |
C8···H19Av | 2.95 (3) | H18A···H15Av | 2.51 (4) |
C9···H8 | 2.74 (2) | H18B···H16B | 2.49 (3) |
C10···H8vii | 3.03 (2) | H18B···H20A | 2.55 (3) |
C10···H8 | 3.09 (2) | H19A···H17B | 2.59 (4) |
C11···H16A | 2.94 (2) | H19A···C8vi | 2.95 (3) |
C13···H10viii | 2.96 (2) | H19B···H17A | 2.44 (3) |
C14···H8 | 2.97 (3) | H20A···H18B | 2.55 (3) |
H1···O1ii | 2.76 (3) | | |
| | | |
C1—N1—C4 | 111.63 (16) | C3—C8—H8 | 121.9 (13) |
C2—N2—C9 | 119.23 (16) | C7—C8—H8 | 119.1 (14) |
C1—N1—H1 | 121.8 (16) | C9—C10—H10 | 120.5 (15) |
C4—N1—H1 | 126.4 (15) | C11—C10—H10 | 119.4 (15) |
N1—C1—C2 | 105.88 (16) | C10—C11—H11 | 118.8 (12) |
O1—C1—C2 | 125.99 (18) | C12—C11—H11 | 119.7 (12) |
O1—C1—N1 | 128.10 (19) | C12—C13—H13 | 120.1 (15) |
N2—C2—C3 | 135.16 (17) | C14—C13—H13 | 117.9 (15) |
C1—C2—C3 | 106.03 (15) | C9—C14—H14 | 118.1 (12) |
N2—C2—C1 | 118.78 (17) | C13—C14—H14 | 122.3 (12) |
C4—C3—C8 | 119.80 (17) | C12—C15—H15A | 108.0 (14) |
C2—C3—C4 | 106.50 (16) | C12—C15—H15B | 109.5 (13) |
C2—C3—C8 | 133.60 (17) | C16—C15—H15A | 108.8 (13) |
C3—C4—C5 | 121.64 (18) | C16—C15—H15B | 110.0 (14) |
N1—C4—C3 | 109.96 (16) | H15A—C15—H15B | 107 (2) |
N1—C4—C5 | 128.40 (17) | C15—C16—H16A | 109.6 (14) |
C4—C5—C6 | 117.46 (18) | C15—C16—H16B | 108.8 (14) |
C5—C6—C7 | 121.97 (19) | C17—C16—H16A | 108.1 (14) |
C6—C7—C8 | 120.09 (19) | C17—C16—H16B | 109.1 (13) |
C3—C8—C7 | 119.00 (18) | H16A—C16—H16B | 106 (2) |
C10—C9—C14 | 119.34 (18) | C16—C17—H17A | 108.1 (14) |
N2—C9—C14 | 122.24 (17) | C16—C17—H17B | 111.5 (18) |
N2—C9—C10 | 118.26 (16) | C18—C17—H17A | 108.3 (13) |
C9—C10—C11 | 120.17 (18) | C18—C17—H17B | 113.8 (17) |
C10—C11—C12 | 121.4 (2) | H17A—C17—H17B | 99 (2) |
C13—C12—C15 | 121.99 (19) | C17—C18—H18A | 104.8 (13) |
C11—C12—C13 | 117.37 (19) | C17—C18—H18B | 111.2 (16) |
C11—C12—C15 | 120.63 (19) | C19—C18—H18A | 107.7 (14) |
C12—C13—C14 | 122.02 (19) | C19—C18—H18B | 109.8 (14) |
C9—C14—C13 | 119.63 (19) | H18A—C18—H18B | 107 (2) |
C12—C15—C16 | 113.65 (17) | C18—C19—H19A | 108.6 (14) |
C15—C16—C17 | 114.86 (19) | C18—C19—H19B | 104.7 (14) |
C16—C17—C18 | 114.6 (2) | C20—C19—H19A | 111.7 (15) |
C17—C18—C19 | 115.9 (2) | C20—C19—H19B | 112.1 (13) |
C18—C19—C20 | 115.4 (3) | H19A—C19—H19B | 103 (2) |
C4—C5—H5 | 121.3 (13) | C19—C20—H20A | 112.6 (16) |
C6—C5—H5 | 121.3 (13) | C19—C20—H20B | 112.3 (16) |
C5—C6—H6 | 119.2 (14) | C19—C20—H20C | 108.6 (13) |
C7—C6—H6 | 118.8 (14) | H20A—C20—H20B | 107.1 (19) |
C6—C7—H7 | 119.8 (12) | H20A—C20—H20C | 107 (2) |
C8—C7—H7 | 120.1 (12) | H20B—C20—H20C | 109 (2) |
| | | |
C4—N1—C1—O1 | −177.4 (2) | N1—C4—C5—C6 | 178.12 (19) |
C4—N1—C1—C2 | 0.6 (2) | C3—C4—C5—C6 | −1.3 (3) |
C1—N1—C4—C3 | −0.2 (2) | C4—C5—C6—C7 | −0.3 (3) |
C1—N1—C4—C5 | −179.7 (2) | C5—C6—C7—C8 | 0.8 (3) |
C9—N2—C2—C1 | 172.88 (16) | C6—C7—C8—C3 | 0.2 (3) |
C9—N2—C2—C3 | −4.7 (3) | N2—C9—C10—C11 | −177.12 (17) |
C2—N2—C9—C10 | −87.2 (2) | C10—C9—C14—C13 | 1.8 (3) |
C2—N2—C9—C14 | 97.3 (2) | C14—C9—C10—C11 | −1.6 (3) |
O1—C1—C2—C3 | 177.31 (19) | N2—C9—C14—C13 | 177.20 (18) |
N1—C1—C2—N2 | −178.96 (17) | C9—C10—C11—C12 | 0.1 (3) |
N1—C1—C2—C3 | −0.7 (2) | C10—C11—C12—C15 | −177.5 (2) |
O1—C1—C2—N2 | −0.9 (3) | C10—C11—C12—C13 | 1.1 (3) |
C1—C2—C3—C8 | 176.9 (2) | C11—C12—C13—C14 | −0.8 (3) |
C1—C2—C3—C4 | 0.61 (19) | C15—C12—C13—C14 | 177.8 (2) |
N2—C2—C3—C4 | 178.4 (2) | C11—C12—C15—C16 | 69.0 (3) |
N2—C2—C3—C8 | −5.3 (4) | C13—C12—C15—C16 | −109.6 (2) |
C2—C3—C4—C5 | 179.23 (18) | C12—C13—C14—C9 | −0.6 (3) |
C8—C3—C4—N1 | −177.19 (17) | C12—C15—C16—C17 | 177.5 (2) |
C8—C3—C4—C5 | 2.3 (3) | C15—C16—C17—C18 | −177.3 (2) |
C2—C3—C8—C7 | −177.6 (2) | C16—C17—C18—C19 | 174.0 (2) |
C2—C3—C4—N1 | −0.3 (2) | C17—C18—C19—C20 | −179.6 (2) |
C4—C3—C8—C7 | −1.7 (3) | | |
Symmetry codes: (i) −x, y−1/2, −z−1/2; (ii) −x, y+1/2, −z−1/2; (iii) x, −y+3/2, z−1/2; (iv) −x, −y+1, −z; (v) −x+1, y+1/2, −z+1/2; (vi) −x+1, y−1/2, −z+1/2; (vii) x, −y+1/2, z−1/2; (viii) x, −y+1/2, z+1/2; (ix) x, −y+3/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2ii | 0.88 (3) | 2.22 (3) | 3.069 (2) | 163 (2) |
C5—H5···O1ii | 0.96 (3) | 2.55 (2) | 3.265 (3) | 131.4 (16) |
Symmetry code: (ii) −x, y+1/2, −z−1/2. |
Experimental details
Crystal data |
Chemical formula | C20H22N2O |
Mr | 306.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 17.1506 (2), 9.6464 (2), 10.4167 (2) |
β (°) | 99.693 (2) |
V (Å3) | 1698.75 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.52 × 0.31 × 0.05 |
|
Data collection |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30666, 3326, 2121 |
Rint | 0.089 |
(sin θ/λ)max (Å−1) | 0.617 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.132, 1.05 |
No. of reflections | 3326 |
No. of parameters | 274 |
H-atom treatment | Only H-atom coordinates refined |
Δρmax, Δρmin (e Å−3) | 0.14, −0.18 |
Selected geometric parameters (Å, º) topO1—C1 | 1.213 (3) | N2—C2 | 1.280 (2) |
N1—C1 | 1.357 (3) | N2—C9 | 1.431 (2) |
N1—C4 | 1.408 (3) | | |
| | | |
C1—N1—C4 | 111.63 (16) | N1—C4—C5 | 128.40 (17) |
C2—N2—C9 | 119.23 (16) | N2—C9—C14 | 122.24 (17) |
N1—C1—C2 | 105.88 (16) | N2—C9—C10 | 118.26 (16) |
O1—C1—C2 | 125.99 (18) | C15—C16—C17 | 114.86 (19) |
O1—C1—N1 | 128.10 (19) | C16—C17—C18 | 114.6 (2) |
N2—C2—C3 | 135.16 (17) | C17—C18—C19 | 115.9 (2) |
N2—C2—C1 | 118.78 (17) | C18—C19—C20 | 115.4 (3) |
N1—C4—C3 | 109.96 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2i | 0.88 (3) | 2.22 (3) | 3.069 (2) | 163 (2) |
C5—H5···O1i | 0.96 (3) | 2.55 (2) | 3.265 (3) | 131.4 (16) |
Symmetry code: (i) −x, y+1/2, −z−1/2. |
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The synthetic versality of isatin has lead to the extensive use of this compound in organic synthesis. It has stemmed from the interest in the biological and pharmacological properties of the derivatives (Silva et al., 2001; Pardasani et al., 1999). Isatin and derivatives of isatin have been used as reagents in the dye industry also. Although, it was firstly synthesized nearly hundred years ago, recently it was discovered in mamalian tissues and in body fluid. It was observed that monoamin oxidase was inhibited by isatin and derivatives in in vitro studies.
Schiff bases of isatin were reported to posses antibacterial (Sarangapani & Reddy, 1994; Varma & Nobles, 1975), antifungal (Pandeya et al., 1999), antiviral (Singh et al., 1983), anti-HIV (Pandeya et al., 2000), antiprotozoal (Varma & Khan, 1977) and antihelminthic (Sarciron et al., 1993) activities.
Our interest in this category of ligands is justified by their already proved medical and biological implications (Popp & Pajouhesh, 1982).
In this study, our purpose was to synthesize and characterize of a new Schiff base ligand, as shown in Fig 1. We reported analytical and X-ray crystallographic studies of the title compound, (I).
The C1—C2 bond length of 1.529 (3) Å is longer than the standard value for this type of bond (Allen et al., 1987). The C2—N2—C9 angle is 119.2 (2)°. In the hexyl group, the average value of the bond angle C—C—C is 115.2 (3)° and this group shows a zigzag form. The indol group is planar [maximum displacements are −0.025 (2) Å for C3 and 0.021 (2) Å for C7] and forms a dihedral angle of 88.01 (5)° with the phenyl plane.
To determine the structural and electronic parameters of the investigated isatin derivative, the conformational analyses of the compound and its quantum mechanic optimizations was performed.
The quantum-chemical calculation using the PM3 method showed that the charges at atoms N1, N2 and O1 are 0.0374, 0.0547 and −0.2933 e, respectively. The final heat of formation of the title compound is 5.53 kcal and its total energy is −3326.84 eV. The values of the HOMO and LUMO energies are −9.02078 and −1.05314 eV, respectively. The molecule dipole moment calculated is 4.467 Debye (one-dimensional = 3.33564 × 10−30 Cm) for (I).
The crystal structure is stabilized by N—H···N and C—H···O hydrogen bonds (Fig. 2), the details of which are given in Table 2.