Acta Cryst. (2010). E66, o1423 [ doi:10.1107/S1600536810017769 ]
In the crystal structure of the title compound, C28H21Cl2N, ![[pi]](/logos/entities/pi_rmgif.gif)
- interactions link pairs of molecules into centrosymmetric dimers with a distance of 3.756 (3) Å between the centroids of the pyridine rings. Weak intermolecular C-H
Cl hydrogen bonds further link these dimers into chains propagating along [
01]. The pyridine ring forms dihedral angles of 21.52 (1) and 55.87 (2)°, respectively, with the phenyl ring and the 4-chlorophenyl ring.
The title compound was synthesized by reaction of (Z)-2,6-dibenzylidenecyclohexanone (0.343 g, 1 mmol),ammonium acetate (3.0 g, 0.039 mol) and N-phenacylpyridinium bromide (0.280 g, 1.2 mmol) in refluxing methanol (15 ml) under stirring for 7 h. Single crystals suitable for x-ray measurements were obtained by recrystallization from ethanol at room temperature.
C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93-0.97 Å and Uiso(H)=1.2-1.5Ueq(C).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: NRCVAX (Gabe et al., 1989); 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: WinGX (Farrugia, 1999).
![[Figure 1]](./cv2704fig1thm.gif)
| Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
| C28H21Cl2N | Z = 2 |
| Mr = 442.36 | F(000) = 460 |
| Triclinic, P1 | Dx = 1.345 Mg m−3 |
| Hall symbol: -P 1 | Melting point: 446 K |
| a = 10.0583 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 10.6483 (10) Å | Cell parameters from 25 reflections |
| c = 10.8792 (10) Å | θ = 4–14° |
| α = 82.028 (2)° | µ = 0.31 mm−1 |
| β = 89.345 (1)° | T = 295 K |
| γ = 71.335 (2)° | Block, colorless |
| V = 1092.53 (18) Å3 | 0.23 × 0.20 × 0.19 mm |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.014 |
| Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.9° |
| graphite | h = −10→11 |
| ω scans | k = −10→12 |
| 5765 measured reflections | l = −12→12 |
| 3810 independent reflections | 3 standard reflections every 100 reflections |
| 3211 reflections with I > 2σ(I) | intensity decay: none |
| 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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.102 | H-atom parameters constrained |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.049P)2 + 0.2862P] where P = (Fo2 + 2Fc2)/3 |
| 3810 reflections | (Δ/σ)max < 0.001 |
| 280 parameters | Δρmax = 0.20 e Å−3 |
| 0 restraints | Δρmin = −0.30 e Å−3 |
| C28H21Cl2N | γ = 71.335 (2)° |
| Mr = 442.36 | V = 1092.53 (18) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 10.0583 (10) Å | Mo Kα radiation |
| b = 10.6483 (10) Å | µ = 0.31 mm−1 |
| c = 10.8792 (10) Å | T = 295 K |
| α = 82.028 (2)° | 0.23 × 0.20 × 0.19 mm |
| β = 89.345 (1)° |
| Enraf–Nonius CAD-4 diffractometer | Rint = 0.014 |
| 5765 measured reflections | θmax = 25.0° |
| 3810 independent reflections | 3 standard reflections every 100 reflections |
| 3211 reflections with I > 2σ(I) | intensity decay: none |
| R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
| wR(F2) = 0.102 | Δρmax = 0.20 e Å−3 |
| S = 1.06 | Δρmin = −0.30 e Å−3 |
| 3810 reflections | Absolute structure: ? |
| 280 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
| Cl1 | 0.76136 (6) | −0.12681 (6) | −0.49616 (5) | 0.06911 (19) | |
| Cl2 | −0.44155 (6) | 0.60618 (5) | 0.38242 (6) | 0.0742 (2) | |
| N1 | 0.17509 (14) | −0.06763 (13) | 0.09541 (12) | 0.0368 (3) | |
| C1 | 0.45331 (19) | −0.14359 (18) | −0.27005 (16) | 0.0451 (4) | |
| H1B | 0.3983 | −0.1989 | −0.2522 | 0.054* | |
| C2 | 0.5506 (2) | −0.17024 (19) | −0.36113 (17) | 0.0489 (4) | |
| H2A | 0.5600 | −0.2415 | −0.4049 | 0.059* | |
| C3 | 0.63328 (18) | −0.09032 (19) | −0.38617 (16) | 0.0458 (4) | |
| C4 | 0.61789 (19) | 0.0167 (2) | −0.32375 (17) | 0.0499 (5) | |
| H4A | 0.6740 | 0.0710 | −0.3420 | 0.060* | |
| C5 | 0.51923 (19) | 0.04352 (18) | −0.23411 (16) | 0.0451 (4) | |
| H5A | 0.5089 | 0.1167 | −0.1928 | 0.054* | |
| C6 | 0.43443 (17) | −0.03640 (16) | −0.20368 (15) | 0.0374 (4) | |
| C7 | 0.33130 (17) | −0.02208 (16) | −0.10601 (15) | 0.0379 (4) | |
| H7A | 0.2986 | −0.0948 | −0.0881 | 0.045* | |
| C8 | 0.27524 (16) | 0.07649 (16) | −0.03750 (15) | 0.0350 (4) | |
| C9 | 0.30828 (19) | 0.20661 (17) | −0.04971 (16) | 0.0416 (4) | |
| H9A | 0.2820 | 0.2535 | −0.1333 | 0.050* | |
| H9B | 0.4088 | 0.1863 | −0.0380 | 0.050* | |
| C10 | 0.23390 (19) | 0.29860 (17) | 0.04218 (17) | 0.0441 (4) | |
| H10A | 0.2800 | 0.2652 | 0.1235 | 0.053* | |
| H10B | 0.2405 | 0.3873 | 0.0166 | 0.053* | |
| C11 | 0.08054 (18) | 0.30767 (16) | 0.05054 (16) | 0.0424 (4) | |
| H11A | 0.0344 | 0.3694 | 0.1073 | 0.051* | |
| H11B | 0.0336 | 0.3405 | −0.0305 | 0.051* | |
| C12 | 0.07233 (17) | 0.17042 (16) | 0.09631 (14) | 0.0355 (4) | |
| C13 | 0.17015 (16) | 0.05872 (16) | 0.05496 (14) | 0.0345 (4) | |
| C14 | 0.08518 (17) | −0.08920 (16) | 0.18078 (15) | 0.0369 (4) | |
| C15 | 0.09818 (18) | −0.23138 (16) | 0.22446 (15) | 0.0386 (4) | |
| C16 | 0.2229 (2) | −0.33247 (17) | 0.21094 (17) | 0.0473 (4) | |
| H16A | 0.2978 | −0.3108 | 0.1735 | 0.057* | |
| C17 | 0.2370 (2) | −0.46471 (19) | 0.25232 (19) | 0.0578 (5) | |
| H17A | 0.3211 | −0.5313 | 0.2426 | 0.069* | |
| C18 | 0.1272 (3) | −0.4986 (2) | 0.30786 (19) | 0.0610 (6) | |
| H18A | 0.1370 | −0.5877 | 0.3361 | 0.073* | |
| C19 | 0.0030 (2) | −0.3998 (2) | 0.32122 (18) | 0.0578 (5) | |
| H19A | −0.0716 | −0.4223 | 0.3585 | 0.069* | |
| C20 | −0.0120 (2) | −0.26712 (18) | 0.27962 (16) | 0.0469 (4) | |
| H20A | −0.0968 | −0.2011 | 0.2887 | 0.056* | |
| C21 | −0.01285 (18) | 0.01573 (17) | 0.22810 (15) | 0.0399 (4) | |
| H21A | −0.0728 | −0.0021 | 0.2887 | 0.048* | |
| C22 | −0.02151 (17) | 0.14700 (16) | 0.18517 (15) | 0.0369 (4) | |
| C23 | −0.12942 (17) | 0.25829 (16) | 0.23450 (15) | 0.0380 (4) | |
| C24 | −0.13747 (19) | 0.26296 (18) | 0.36124 (16) | 0.0460 (4) | |
| H24A | −0.0763 | 0.1944 | 0.4158 | 0.055* | |
| C25 | −0.2349 (2) | 0.3679 (2) | 0.40779 (18) | 0.0513 (5) | |
| H25A | −0.2389 | 0.3706 | 0.4929 | 0.062* | |
| C26 | −0.32574 (19) | 0.46814 (18) | 0.32692 (18) | 0.0467 (4) | |
| C27 | −0.32402 (19) | 0.46397 (18) | 0.20151 (17) | 0.0472 (4) | |
| H27A | −0.3884 | 0.5307 | 0.1478 | 0.057* | |
| C28 | −0.22516 (19) | 0.35909 (18) | 0.15609 (16) | 0.0444 (4) | |
| H28A | −0.2230 | 0.3563 | 0.0710 | 0.053* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0586 (3) | 0.0873 (4) | 0.0505 (3) | −0.0087 (3) | 0.0250 (2) | −0.0108 (3) |
| Cl2 | 0.0743 (4) | 0.0533 (3) | 0.0875 (4) | −0.0030 (3) | 0.0244 (3) | −0.0288 (3) |
| N1 | 0.0408 (8) | 0.0361 (7) | 0.0351 (7) | −0.0139 (6) | 0.0084 (6) | −0.0076 (6) |
| C1 | 0.0467 (10) | 0.0434 (10) | 0.0459 (10) | −0.0140 (8) | 0.0093 (8) | −0.0106 (8) |
| C2 | 0.0527 (11) | 0.0490 (11) | 0.0418 (10) | −0.0086 (9) | 0.0090 (8) | −0.0146 (8) |
| C3 | 0.0396 (9) | 0.0550 (11) | 0.0329 (9) | −0.0034 (8) | 0.0076 (7) | −0.0024 (8) |
| C4 | 0.0466 (10) | 0.0575 (11) | 0.0476 (10) | −0.0201 (9) | 0.0113 (8) | −0.0067 (9) |
| C5 | 0.0487 (10) | 0.0481 (10) | 0.0433 (10) | −0.0199 (8) | 0.0123 (8) | −0.0129 (8) |
| C6 | 0.0365 (9) | 0.0383 (9) | 0.0341 (8) | −0.0079 (7) | 0.0044 (7) | −0.0047 (7) |
| C7 | 0.0384 (9) | 0.0370 (9) | 0.0394 (9) | −0.0139 (7) | 0.0063 (7) | −0.0058 (7) |
| C8 | 0.0359 (8) | 0.0346 (8) | 0.0340 (8) | −0.0112 (7) | 0.0044 (7) | −0.0043 (7) |
| C9 | 0.0459 (10) | 0.0403 (9) | 0.0420 (9) | −0.0179 (8) | 0.0111 (8) | −0.0083 (7) |
| C10 | 0.0540 (11) | 0.0386 (9) | 0.0459 (10) | −0.0221 (8) | 0.0124 (8) | −0.0107 (8) |
| C11 | 0.0495 (10) | 0.0340 (9) | 0.0435 (10) | −0.0126 (8) | 0.0118 (8) | −0.0075 (7) |
| C12 | 0.0390 (9) | 0.0358 (8) | 0.0335 (8) | −0.0138 (7) | 0.0046 (7) | −0.0068 (7) |
| C13 | 0.0375 (8) | 0.0347 (8) | 0.0324 (8) | −0.0128 (7) | 0.0042 (7) | −0.0061 (7) |
| C14 | 0.0412 (9) | 0.0366 (9) | 0.0341 (8) | −0.0140 (7) | 0.0048 (7) | −0.0060 (7) |
| C15 | 0.0501 (10) | 0.0369 (9) | 0.0318 (8) | −0.0172 (8) | 0.0051 (7) | −0.0079 (7) |
| C16 | 0.0546 (11) | 0.0410 (10) | 0.0474 (10) | −0.0159 (9) | 0.0080 (8) | −0.0092 (8) |
| C17 | 0.0697 (13) | 0.0384 (10) | 0.0611 (12) | −0.0105 (10) | 0.0032 (10) | −0.0101 (9) |
| C18 | 0.0920 (16) | 0.0391 (10) | 0.0557 (12) | −0.0284 (11) | −0.0012 (11) | −0.0016 (9) |
| C19 | 0.0783 (14) | 0.0561 (12) | 0.0498 (11) | −0.0386 (11) | 0.0104 (10) | −0.0032 (9) |
| C20 | 0.0570 (11) | 0.0467 (10) | 0.0413 (10) | −0.0223 (9) | 0.0104 (8) | −0.0075 (8) |
| C21 | 0.0427 (9) | 0.0415 (9) | 0.0376 (9) | −0.0163 (8) | 0.0123 (7) | −0.0071 (7) |
| C22 | 0.0380 (9) | 0.0380 (9) | 0.0351 (9) | −0.0116 (7) | 0.0053 (7) | −0.0081 (7) |
| C23 | 0.0385 (9) | 0.0375 (9) | 0.0413 (9) | −0.0156 (7) | 0.0098 (7) | −0.0089 (7) |
| C24 | 0.0453 (10) | 0.0474 (10) | 0.0414 (10) | −0.0088 (8) | 0.0056 (8) | −0.0087 (8) |
| C25 | 0.0536 (11) | 0.0579 (12) | 0.0438 (10) | −0.0153 (9) | 0.0106 (9) | −0.0192 (9) |
| C26 | 0.0459 (10) | 0.0398 (10) | 0.0579 (11) | −0.0161 (8) | 0.0174 (9) | −0.0149 (8) |
| C27 | 0.0452 (10) | 0.0391 (10) | 0.0522 (11) | −0.0094 (8) | 0.0067 (8) | 0.0004 (8) |
| C28 | 0.0490 (10) | 0.0446 (10) | 0.0387 (9) | −0.0144 (8) | 0.0093 (8) | −0.0049 (8) |
| Cl1—C3 | 1.7366 (17) | C12—C22 | 1.397 (2) |
| Cl2—C26 | 1.7367 (17) | C12—C13 | 1.405 (2) |
| N1—C14 | 1.337 (2) | C14—C21 | 1.389 (2) |
| N1—C13 | 1.342 (2) | C14—C15 | 1.487 (2) |
| C1—C2 | 1.378 (2) | C15—C20 | 1.387 (2) |
| C1—C6 | 1.395 (2) | C15—C16 | 1.389 (2) |
| C1—H1B | 0.9300 | C16—C17 | 1.380 (3) |
| C2—C3 | 1.368 (3) | C16—H16A | 0.9300 |
| C2—H2A | 0.9300 | C17—C18 | 1.376 (3) |
| C3—C4 | 1.373 (3) | C17—H17A | 0.9300 |
| C4—C5 | 1.375 (2) | C18—C19 | 1.373 (3) |
| C4—H4A | 0.9300 | C18—H18A | 0.9300 |
| C5—C6 | 1.393 (2) | C19—C20 | 1.383 (3) |
| C5—H5A | 0.9300 | C19—H19A | 0.9300 |
| C6—C7 | 1.465 (2) | C20—H20A | 0.9300 |
| C7—C8 | 1.343 (2) | C21—C22 | 1.386 (2) |
| C7—H7A | 0.9300 | C21—H21A | 0.9300 |
| C8—C13 | 1.489 (2) | C22—C23 | 1.487 (2) |
| C8—C9 | 1.513 (2) | C23—C28 | 1.382 (2) |
| C9—C10 | 1.518 (2) | C23—C24 | 1.387 (2) |
| C9—H9A | 0.9700 | C24—C25 | 1.382 (2) |
| C9—H9B | 0.9700 | C24—H24A | 0.9300 |
| C10—C11 | 1.517 (2) | C25—C26 | 1.372 (3) |
| C10—H10A | 0.9700 | C25—H25A | 0.9300 |
| C10—H10B | 0.9700 | C26—C27 | 1.371 (3) |
| C11—C12 | 1.505 (2) | C27—C28 | 1.382 (2) |
| C11—H11A | 0.9700 | C27—H27A | 0.9300 |
| C11—H11B | 0.9700 | C28—H28A | 0.9300 |
| C14—N1—C13 | 118.91 (14) | N1—C13—C8 | 116.56 (13) |
| C2—C1—C6 | 122.23 (17) | C12—C13—C8 | 120.52 (14) |
| C2—C1—H1B | 118.9 | N1—C14—C21 | 121.64 (15) |
| C6—C1—H1B | 118.9 | N1—C14—C15 | 116.46 (14) |
| C3—C2—C1 | 119.02 (17) | C21—C14—C15 | 121.88 (14) |
| C3—C2—H2A | 120.5 | C20—C15—C16 | 118.21 (16) |
| C1—C2—H2A | 120.5 | C20—C15—C14 | 121.62 (16) |
| C2—C3—C4 | 120.79 (16) | C16—C15—C14 | 120.16 (15) |
| C2—C3—Cl1 | 119.54 (14) | C17—C16—C15 | 120.80 (18) |
| C4—C3—Cl1 | 119.66 (15) | C17—C16—H16A | 119.6 |
| C3—C4—C5 | 119.74 (18) | C15—C16—H16A | 119.6 |
| C3—C4—H4A | 120.1 | C18—C17—C16 | 120.35 (19) |
| C5—C4—H4A | 120.1 | C18—C17—H17A | 119.8 |
| C4—C5—C6 | 121.59 (17) | C16—C17—H17A | 119.8 |
| C4—C5—H5A | 119.2 | C19—C18—C17 | 119.53 (18) |
| C6—C5—H5A | 119.2 | C19—C18—H18A | 120.2 |
| C5—C6—C1 | 116.61 (15) | C17—C18—H18A | 120.2 |
| C5—C6—C7 | 126.52 (15) | C18—C19—C20 | 120.41 (19) |
| C1—C6—C7 | 116.83 (15) | C18—C19—H19A | 119.8 |
| C8—C7—C6 | 131.97 (16) | C20—C19—H19A | 119.8 |
| C8—C7—H7A | 114.0 | C19—C20—C15 | 120.70 (19) |
| C6—C7—H7A | 114.0 | C19—C20—H20A | 119.7 |
| C7—C8—C13 | 117.97 (14) | C15—C20—H20A | 119.7 |
| C7—C8—C9 | 124.69 (14) | C22—C21—C14 | 120.16 (15) |
| C13—C8—C9 | 117.31 (13) | C22—C21—H21A | 119.9 |
| C8—C9—C10 | 113.80 (13) | C14—C21—H21A | 119.9 |
| C8—C9—H9A | 108.8 | C21—C22—C12 | 118.56 (15) |
| C10—C9—H9A | 108.8 | C21—C22—C23 | 119.49 (14) |
| C8—C9—H9B | 108.8 | C12—C22—C23 | 121.95 (14) |
| C10—C9—H9B | 108.8 | C28—C23—C24 | 118.10 (16) |
| H9A—C9—H9B | 107.7 | C28—C23—C22 | 121.24 (15) |
| C11—C10—C9 | 111.40 (14) | C24—C23—C22 | 120.66 (16) |
| C11—C10—H10A | 109.3 | C25—C24—C23 | 121.08 (17) |
| C9—C10—H10A | 109.3 | C25—C24—H24A | 119.5 |
| C11—C10—H10B | 109.3 | C23—C24—H24A | 119.5 |
| C9—C10—H10B | 109.3 | C26—C25—C24 | 119.17 (17) |
| H10A—C10—H10B | 108.0 | C26—C25—H25A | 120.4 |
| C12—C11—C10 | 108.64 (14) | C24—C25—H25A | 120.4 |
| C12—C11—H11A | 110.0 | C27—C26—C25 | 121.19 (17) |
| C10—C11—H11A | 110.0 | C27—C26—Cl2 | 118.83 (15) |
| C12—C11—H11B | 110.0 | C25—C26—Cl2 | 119.95 (15) |
| C10—C11—H11B | 110.0 | C26—C27—C28 | 119.02 (17) |
| H11A—C11—H11B | 108.3 | C26—C27—H27A | 120.5 |
| C22—C12—C13 | 117.77 (14) | C28—C27—H27A | 120.5 |
| C22—C12—C11 | 123.25 (14) | C23—C28—C27 | 121.37 (16) |
| C13—C12—C11 | 118.81 (14) | C23—C28—H28A | 119.3 |
| N1—C13—C12 | 122.92 (14) | C27—C28—H28A | 119.3 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C7—H7A···N1 | 0.93 | 2.34 | 2.760 (2) | 107 |
| C20—H20A···Cl1i | 0.93 | 2.80 | 3.476 (2) | 130 |
| Symmetry codes: (i) x−1, y, z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C20—H20A···Cl1i | 0.93 | 2.80 | 3.476 (2) | 130 |
| Symmetry codes: (i) x−1, y, z+1. |
The authors thank the Natural Science Foundation of Shandong Province (grant Nos. Y2006B08 & Z2007B01).
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The pyridyl heterocyclic core occurs in many natural products (Barton & Ollis, 1979; Katritzky & Marson, 1984). It also plays an important role in various coordinating ligands (Constable et al., 1994; Eryazici et al., 2006)˙ Recently, the structure of 5,6,7,8-tetrahydroquinoline derivative has been reported (Yan et al., 2007). Herein, we report the crystal structure of the title compound.
In (I) (Fig. 1), the bond lengths and angles are in a good agreement with those reported previously (Yan et al., 2007). Rings N1/C13/C12/C22/C21/C14 (p1), C15-C20 (p2), C23-C28 (p3) and C1-C6 (p4) form the following dihedral angles - p1/p2 21.52 (1)°, p1/p3 55.87 (2)°, p1/p4 33.74 (1)°, p2/p3 67.85 (1)°, p2/p4 44.53 (2)° and p3/p4 81.57 (1)°.
The crystal packing is stabilized by hydrogen bonds and π-π interactions. π-π interaction link two molecules into centrosymmetric dimer with the distance of 3.756 (3) Å between the centroids of pyridine rings. Weak intermolecular C—H···Cl hydrogen bonds (Table 1) link further these dimers into chains propagated in direction [-101].