Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011291/ya6043sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011291/ya6043Isup2.hkl |
CCDC reference: 170919
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.130
- Data-to-parameter ratio = 18.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.072 Value of mu given = 0.070 PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(7) - C(8) = 1.43 Ang. PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(7) - C(9) = 1.43 Ang. PLAT_601 Alert C Structure Contains Solvent Accessible VOIDS of 37.00 A 3
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
4 Alert Level C = Please check
The title compound was synthesized according to the general procedure described by Lemke (1970). The preparation of the starting compound, [3,5,5-trimethyl(cyclohex-2-enylidene)]malonodinitrile, C12H14N2, is described in one of our previous papers (Kolev et al., 2001). The starting compound (6 mmol, 20% excess) was dissolved in 80 ml of dry toluene under continuous stirring. Indole-3-aldehyde (5 mmol Across), dissolved in 50 ml of dry toluene, was added to the solution. Nearly 1 ml of triethylamine was used as a catalyst. The solution became dark-red after a few minutes and the resulting compound started precipitating. After 16 h reaction time, the solution was cooled and the resulting title compound was isolated and recrystallized twice from glacial acetic acid and from dry toluene [m.p. 519–521 K; literature m.p. 520–522 K (Lemke, 1970)]. The purity of the compound was confirmed by elemental analysis, IR, UV-vis and mass spectrometry. Crystals were grown from a glacial acetic acid solution by slow evaporation at room temperature over a period of several weeks.
H atoms were placed in calculated positions with Uiso constrained to be 1.5Ueq of the carrier atom for the methyl H atoms and 1.2Ueq for the remaining H atoms.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) PLATON (Spek, 2001).
Fig. 1. View of the title compound showing the labelling of all non-H atoms. Displacement ellipsoids are shown at 50% probability levels. H atoms are drawn as circles of arbitrary radii. |
C21H19N3 | F(000) = 664 |
Mr = 313.39 | Dx = 1.195 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 15.5033 (3) Å | Cell parameters from 15212 reflections |
b = 7.5309 (2) Å | θ = 3.0–27.5° |
c = 15.9609 (4) Å | µ = 0.07 mm−1 |
β = 110.774 (1)° | T = 291 K |
V = 1742.34 (7) Å3 | Plate, red |
Z = 4 | 0.40 × 0.30 × 0.05 mm |
Nonius KappaCCD diffractometer | 1785 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
Detector resolution: 10 vertical, 18 horizontal pixels mm-1 | h = −20→20 |
292 frames via ω–rotation (Δω=1°) with 3 sets at different κ–angles and two times 20 s per frame scans | k = −9→9 |
3946 measured reflections | l = −20→18 |
3946 independent 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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0595P)2] where P = (Fo2 + 2Fc2)/3 |
3946 reflections | (Δ/σ)max < 0.001 |
219 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C21H19N3 | V = 1742.34 (7) Å3 |
Mr = 313.39 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.5033 (3) Å | µ = 0.07 mm−1 |
b = 7.5309 (2) Å | T = 291 K |
c = 15.9609 (4) Å | 0.40 × 0.30 × 0.05 mm |
β = 110.774 (1)° |
Nonius KappaCCD diffractometer | 1785 reflections with I > 2σ(I) |
3946 measured reflections | Rint = 0.027 |
3946 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 0.92 | Δρmax = 0.13 e Å−3 |
3946 reflections | Δρmin = −0.18 e Å−3 |
219 parameters |
Experimental. The data collection covered the whole sphere of reciprocal space. The crystal-to-detector distance was 34 mm. Crystal decay was monitored by repeating the initial frames at the end of data collection and analysing the duplicate reflections. |
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 | ||
N1 | 0.77182 (14) | 0.7498 (3) | 0.33635 (14) | 0.1010 (7) | |
N2 | 0.92484 (13) | 0.2631 (3) | 0.36515 (14) | 0.0878 (6) | |
N3 | 1.31308 (10) | 0.3652 (2) | −0.01387 (11) | 0.0607 (5) | |
H3 | 1.3479 | 0.3771 | −0.0452 | 0.073* | |
C1 | 1.03138 (11) | 0.5987 (2) | 0.14831 (11) | 0.0422 (4) | |
C2 | 0.98908 (11) | 0.5345 (2) | 0.20362 (11) | 0.0454 (5) | |
H2 | 1.0038 | 0.4203 | 0.2264 | 0.054* | |
C3 | 0.92340 (11) | 0.6330 (2) | 0.22840 (12) | 0.0446 (5) | |
C4 | 0.89425 (11) | 0.8097 (2) | 0.18518 (12) | 0.0478 (5) | |
H4A | 0.8739 | 0.8831 | 0.2245 | 0.057* | |
H4B | 0.8421 | 0.7931 | 0.1299 | 0.057* | |
C5 | 0.97066 (11) | 0.9071 (2) | 0.16431 (11) | 0.0433 (5) | |
C6 | 1.00848 (12) | 0.7823 (2) | 0.10977 (12) | 0.0476 (5) | |
H6A | 0.9632 | 0.7728 | 0.0496 | 0.057* | |
H6B | 1.0637 | 0.8349 | 0.1051 | 0.057* | |
C7 | 0.88658 (12) | 0.5679 (2) | 0.28792 (13) | 0.0513 (5) | |
C8 | 0.82267 (15) | 0.6688 (3) | 0.31439 (14) | 0.0672 (6) | |
C9 | 0.90860 (13) | 0.3979 (3) | 0.32954 (14) | 0.0608 (6) | |
C10 | 0.93022 (13) | 1.0729 (2) | 0.10920 (13) | 0.0588 (5) | |
H10A | 0.8823 | 1.0389 | 0.0544 | 0.088* | |
H10B | 0.9779 | 1.1345 | 0.0957 | 0.088* | |
H10C | 0.9051 | 1.1494 | 0.1429 | 0.088* | |
C11 | 1.04724 (12) | 0.9601 (2) | 0.25218 (13) | 0.0590 (5) | |
H11A | 1.0221 | 1.0361 | 0.2861 | 0.088* | |
H11B | 1.0950 | 1.0220 | 0.2390 | 0.088* | |
H11C | 1.0725 | 0.8554 | 0.2864 | 0.088* | |
C12 | 1.09727 (11) | 0.4906 (2) | 0.12729 (11) | 0.0467 (5) | |
H12 | 1.1090 | 0.3790 | 0.1538 | 0.056* | |
C13 | 1.14364 (11) | 0.5335 (2) | 0.07342 (11) | 0.0485 (5) | |
H13 | 1.1312 | 0.6453 | 0.0471 | 0.058* | |
C14 | 1.21002 (11) | 0.4295 (2) | 0.05107 (12) | 0.0460 (5) | |
C15 | 1.24434 (11) | 0.2509 (2) | 0.07679 (11) | 0.0444 (5) | |
C16 | 1.22783 (12) | 0.1170 (3) | 0.12974 (12) | 0.0535 (5) | |
H16 | 1.1869 | 0.1360 | 0.1596 | 0.064* | |
C17 | 1.27243 (13) | −0.0424 (3) | 0.13735 (13) | 0.0637 (6) | |
H17 | 1.2606 | −0.1318 | 0.1720 | 0.076* | |
C18 | 1.33486 (14) | −0.0740 (3) | 0.09456 (14) | 0.0692 (6) | |
H18 | 1.3640 | −0.1837 | 0.1009 | 0.083* | |
C19 | 1.35395 (13) | 0.0548 (3) | 0.04322 (14) | 0.0650 (6) | |
H19 | 1.3963 | 0.0351 | 0.0151 | 0.078* | |
C20 | 1.30800 (12) | 0.2156 (3) | 0.03455 (12) | 0.0510 (5) | |
C21 | 1.25459 (12) | 0.4895 (3) | −0.00406 (12) | 0.0569 (5) | |
H21 | 1.2457 | 0.6008 | −0.0310 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.1147 (17) | 0.1093 (17) | 0.1101 (17) | 0.0341 (13) | 0.0783 (15) | 0.0100 (13) |
N2 | 0.1057 (15) | 0.0763 (15) | 0.1108 (17) | 0.0105 (12) | 0.0747 (14) | 0.0251 (12) |
N3 | 0.0642 (10) | 0.0671 (12) | 0.0694 (12) | −0.0082 (9) | 0.0467 (9) | −0.0109 (10) |
C1 | 0.0467 (10) | 0.0404 (11) | 0.0433 (11) | 0.0001 (9) | 0.0208 (9) | −0.0008 (9) |
C2 | 0.0530 (11) | 0.0398 (11) | 0.0506 (13) | 0.0008 (9) | 0.0272 (10) | 0.0008 (9) |
C3 | 0.0455 (10) | 0.0441 (11) | 0.0476 (12) | −0.0033 (9) | 0.0207 (9) | −0.0032 (9) |
C4 | 0.0500 (10) | 0.0462 (11) | 0.0522 (12) | 0.0031 (9) | 0.0242 (9) | 0.0003 (9) |
C5 | 0.0483 (10) | 0.0384 (10) | 0.0467 (12) | 0.0016 (8) | 0.0211 (9) | −0.0001 (9) |
C6 | 0.0535 (11) | 0.0469 (11) | 0.0478 (12) | −0.0003 (9) | 0.0246 (9) | 0.0000 (9) |
C7 | 0.0555 (11) | 0.0500 (12) | 0.0610 (13) | 0.0014 (10) | 0.0363 (11) | 0.0006 (10) |
C8 | 0.0755 (14) | 0.0720 (15) | 0.0717 (16) | 0.0094 (12) | 0.0479 (13) | 0.0080 (12) |
C9 | 0.0675 (13) | 0.0628 (15) | 0.0723 (15) | −0.0005 (11) | 0.0495 (12) | 0.0060 (13) |
C10 | 0.0698 (12) | 0.0455 (12) | 0.0654 (14) | 0.0057 (10) | 0.0293 (11) | 0.0042 (10) |
C11 | 0.0638 (12) | 0.0567 (13) | 0.0577 (14) | −0.0048 (10) | 0.0232 (11) | −0.0073 (10) |
C12 | 0.0545 (11) | 0.0420 (11) | 0.0499 (12) | 0.0041 (9) | 0.0264 (10) | −0.0001 (9) |
C13 | 0.0584 (11) | 0.0463 (12) | 0.0486 (12) | −0.0002 (9) | 0.0285 (10) | −0.0013 (9) |
C14 | 0.0497 (10) | 0.0471 (12) | 0.0494 (12) | −0.0056 (9) | 0.0275 (9) | −0.0045 (9) |
C15 | 0.0421 (10) | 0.0498 (12) | 0.0436 (12) | −0.0041 (9) | 0.0181 (9) | −0.0072 (9) |
C16 | 0.0523 (11) | 0.0565 (13) | 0.0545 (13) | 0.0003 (10) | 0.0223 (10) | 0.0000 (10) |
C17 | 0.0651 (13) | 0.0589 (14) | 0.0625 (15) | 0.0031 (11) | 0.0172 (11) | 0.0058 (11) |
C18 | 0.0653 (14) | 0.0623 (15) | 0.0700 (16) | 0.0147 (11) | 0.0115 (12) | −0.0073 (12) |
C19 | 0.0533 (12) | 0.0767 (16) | 0.0665 (15) | 0.0080 (12) | 0.0234 (11) | −0.0165 (12) |
C20 | 0.0471 (10) | 0.0578 (13) | 0.0514 (13) | −0.0052 (10) | 0.0216 (10) | −0.0109 (10) |
C21 | 0.0688 (13) | 0.0521 (12) | 0.0621 (14) | −0.0065 (11) | 0.0384 (11) | −0.0059 (10) |
N1—C8 | 1.146 (2) | C10—H10B | 0.9600 |
N2—C9 | 1.147 (2) | C10—H10C | 0.9600 |
N3—C21 | 1.350 (2) | C11—H11A | 0.9600 |
N3—C20 | 1.384 (2) | C11—H11B | 0.9600 |
N3—H3 | 0.8600 | C11—H11C | 0.9600 |
C1—C2 | 1.362 (2) | C12—C13 | 1.341 (2) |
C1—C12 | 1.436 (2) | C12—H12 | 0.9300 |
C1—C6 | 1.504 (2) | C13—C14 | 1.436 (2) |
C2—C3 | 1.425 (2) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C21 | 1.374 (2) |
C3—C7 | 1.361 (2) | C14—C15 | 1.451 (2) |
C3—C4 | 1.493 (2) | C15—C16 | 1.397 (2) |
C4—C5 | 1.527 (2) | C15—C20 | 1.404 (2) |
C4—H4A | 0.9700 | C16—C17 | 1.370 (3) |
C4—H4B | 0.9700 | C16—H16 | 0.9300 |
C5—C10 | 1.528 (2) | C17—C18 | 1.389 (3) |
C5—C6 | 1.532 (2) | C17—H17 | 0.9300 |
C5—C11 | 1.535 (2) | C18—C19 | 1.368 (3) |
C6—H6A | 0.9700 | C18—H18 | 0.9300 |
C6—H6B | 0.9700 | C19—C20 | 1.387 (3) |
C7—C8 | 1.426 (3) | C19—H19 | 0.9300 |
C7—C9 | 1.427 (3) | C21—H21 | 0.9300 |
C10—H10A | 0.9600 | ||
C21—N3—C20 | 109.03 (15) | H10A—C10—H10C | 109.5 |
C21—N3—H3 | 125.5 | H10B—C10—H10C | 109.5 |
C20—N3—H3 | 125.5 | C5—C11—H11A | 109.5 |
C2—C1—C12 | 119.74 (16) | C5—C11—H11B | 109.5 |
C2—C1—C6 | 119.60 (15) | H11A—C11—H11B | 109.5 |
C12—C1—C6 | 120.66 (15) | C5—C11—H11C | 109.5 |
C1—C2—C3 | 123.42 (17) | H11A—C11—H11C | 109.5 |
C1—C2—H2 | 118.3 | H11B—C11—H11C | 109.5 |
C3—C2—H2 | 118.3 | C13—C12—C1 | 126.93 (17) |
C7—C3—C2 | 121.61 (17) | C13—C12—H12 | 116.5 |
C7—C3—C4 | 120.68 (15) | C1—C12—H12 | 116.5 |
C2—C3—C4 | 117.70 (15) | C12—C13—C14 | 128.49 (18) |
C3—C4—C5 | 113.43 (14) | C12—C13—H13 | 115.8 |
C3—C4—H4A | 108.9 | C14—C13—H13 | 115.8 |
C5—C4—H4A | 108.9 | C21—C14—C13 | 123.19 (18) |
C3—C4—H4B | 108.9 | C21—C14—C15 | 105.60 (15) |
C5—C4—H4B | 108.9 | C13—C14—C15 | 131.22 (16) |
H4A—C4—H4B | 107.7 | C16—C15—C20 | 117.69 (17) |
C4—C5—C10 | 109.05 (14) | C16—C15—C14 | 135.48 (16) |
C4—C5—C6 | 108.20 (14) | C20—C15—C14 | 106.83 (16) |
C10—C5—C6 | 109.61 (14) | C17—C16—C15 | 119.46 (18) |
C4—C5—C11 | 109.53 (14) | C17—C16—H16 | 120.3 |
C10—C5—C11 | 109.86 (14) | C15—C16—H16 | 120.3 |
C6—C5—C11 | 110.56 (13) | C16—C17—C18 | 121.6 (2) |
C1—C6—C5 | 114.44 (14) | C16—C17—H17 | 119.2 |
C1—C6—H6A | 108.6 | C18—C17—H17 | 119.2 |
C5—C6—H6A | 108.6 | C19—C18—C17 | 120.66 (19) |
C1—C6—H6B | 108.6 | C19—C18—H18 | 119.7 |
C5—C6—H6B | 108.6 | C17—C18—H18 | 119.7 |
H6A—C6—H6B | 107.6 | C18—C19—C20 | 117.79 (19) |
C3—C7—C8 | 121.46 (18) | C18—C19—H19 | 121.1 |
C3—C7—C9 | 123.89 (16) | C20—C19—H19 | 121.1 |
C8—C7—C9 | 114.64 (16) | N3—C20—C19 | 129.62 (18) |
N1—C8—C7 | 179.5 (2) | N3—C20—C15 | 107.62 (16) |
N2—C9—C7 | 177.5 (2) | C19—C20—C15 | 122.76 (19) |
C5—C10—H10A | 109.5 | N3—C21—C14 | 110.92 (18) |
C5—C10—H10B | 109.5 | N3—C21—H21 | 124.5 |
H10A—C10—H10B | 109.5 | C14—C21—H21 | 124.5 |
C5—C10—H10C | 109.5 | ||
C12—C1—C2—C3 | 179.59 (15) | C12—C13—C14—C15 | 1.9 (3) |
C6—C1—C2—C3 | −0.5 (3) | C21—C14—C15—C16 | −179.28 (19) |
C1—C2—C3—C7 | −176.18 (16) | C13—C14—C15—C16 | 0.2 (3) |
C1—C2—C3—C4 | 5.2 (3) | C21—C14—C15—C20 | −0.09 (19) |
C7—C3—C4—C5 | 148.38 (16) | C13—C14—C15—C20 | 179.40 (18) |
C2—C3—C4—C5 | −33.0 (2) | C20—C15—C16—C17 | −1.0 (3) |
C3—C4—C5—C10 | 172.35 (15) | C14—C15—C16—C17 | 178.10 (19) |
C3—C4—C5—C6 | 53.19 (19) | C15—C16—C17—C18 | 0.9 (3) |
C3—C4—C5—C11 | −67.40 (19) | C16—C17—C18—C19 | 0.1 (3) |
C2—C1—C6—C5 | 23.8 (2) | C17—C18—C19—C20 | −0.9 (3) |
C12—C1—C6—C5 | −156.27 (15) | C21—N3—C20—C19 | 178.82 (19) |
C4—C5—C6—C1 | −48.67 (19) | C21—N3—C20—C15 | −0.8 (2) |
C10—C5—C6—C1 | −167.48 (14) | C18—C19—C20—N3 | −178.82 (18) |
C11—C5—C6—C1 | 71.28 (18) | C18—C19—C20—C15 | 0.7 (3) |
C2—C3—C7—C8 | 178.32 (17) | C16—C15—C20—N3 | 179.87 (15) |
C4—C3—C7—C8 | −3.1 (3) | C14—C15—C20—N3 | 0.51 (19) |
C2—C3—C7—C9 | −0.8 (3) | C16—C15—C20—C19 | 0.2 (3) |
C4—C3—C7—C9 | 177.77 (18) | C14—C15—C20—C19 | −179.11 (17) |
C2—C1—C12—C13 | 179.10 (17) | C20—N3—C21—C14 | 0.7 (2) |
C6—C1—C12—C13 | −0.8 (3) | C13—C14—C21—N3 | −179.92 (15) |
C1—C12—C13—C14 | 179.81 (16) | C15—C14—C21—N3 | −0.4 (2) |
C12—C13—C14—C21 | −178.73 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N2i | 0.86 | 2.41 | 3.168 (3) | 148 |
C21—H21···N1ii | 0.93 | 2.55 | 3.301 (3) | 138 |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C21H19N3 |
Mr | 313.39 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 291 |
a, b, c (Å) | 15.5033 (3), 7.5309 (2), 15.9609 (4) |
β (°) | 110.774 (1) |
V (Å3) | 1742.34 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.40 × 0.30 × 0.05 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3946, 3946, 1785 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.130, 0.92 |
No. of reflections | 3946 |
No. of parameters | 219 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.18 |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1991), SHELXL97, PARST95 (Nardelli, 1995) PLATON (Spek, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N2i | 0.86 | 2.41 | 3.168 (3) | 148 |
C21—H21···N1ii | 0.93 | 2.55 | 3.301 (3) | 138 |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+3/2, z−1/2. |
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