Acta Cryst. (2008). E64, o831 [ doi:10.1107/S1600536808009239 ]
In the molecule of the title compound, C21H20ClN, the quinoline group is nearly planar and is oriented at a dihedral angle of 77.21 (3)° with respect to the phenyl ring. The conformation of the cyclooctane ring is twist-boat. In the crystal structure, there are some weak ![[pi]](/logos/entities/pi_rmgif.gif)
- interactions [centroid-to-centroid distances of 3.7414 (11) and 3.8633 (12) Å] between the rings of the quinoline groups.
A mixture of 2-amino-5-chlorophenyl(phenyl)methanone (0.23 g, 1 mmol), cyclooctanone (1.26 g, 1 mmol) and Dewax-50 W ion exchange resin (0.3 g) was heated at 353 K. After 2 h the reaction mixture was washed with ethyl acetate (10 ml). Evaporation of the solvent followed by recrystallization from ethanol to afford the pure product (yield; 0.278 g, 75%).
H atoms were positioned geometrically with C-H = 0.93 and 0.97 Å for aromatic and methylene H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
![[Figure 1]](./hk2449fig1thm.gif)
| Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![[Figure 2]](./hk2449fig2thm.gif)
| Fig. 2. A packing diagram of (I). |
| C21H20Cl1N1 | Z = 2 |
| Mr = 321.83 | F000 = 340 |
| Triclinic, P1 | Dx = 1.298 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 9.837 (2) Å | Cell parameters from 2086 reflections |
| b = 9.980 (2) Å | θ = 2.4–28.0º |
| c = 10.175 (2) Å | µ = 0.23 mm−1 |
| α = 74.600 (17)º | T = 298 (2) K |
| β = 70.575 (16)º | Block, colorless |
| γ = 61.829 (15)º | 0.5 × 0.5 × 0.25 mm |
| V = 823.4 (3) Å3 |
| Stoe IPDSII diffractometer | Rint = 0.045 |
| rotation method scans | θmax = 28.0º |
| Absorption correction: numerical shape of crystal determined optically [PROGRAM NAME? reference? | θmin = 2.4º |
| Tmin = 0.889, Tmax = 0.949 | h = −12→11 |
| 8123 measured reflections | k = −13→10 |
| 3801 independent reflections | l = −13→13 |
| 3493 reflections with I > 2σ(I) |
| Refinement on F2 | H-atom parameters constrained |
| Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0607P)2 + 0.1883P] where P = (Fo2 + 2Fc2)/3 |
| R[F2 > 2σ(F2)] = 0.046 | (Δ/σ)max = 0.006 |
| wR(F2) = 0.126 | Δρmax = 0.25 e Å−3 |
| S = 1.04 | Δρmin = −0.19 e Å−3 |
| 3801 reflections | Extinction correction: none |
| 208 parameters |
| C21H20Cl1N1 | γ = 61.829 (15)º |
| Mr = 321.83 | V = 823.4 (3) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 9.837 (2) Å | Mo Kα |
| b = 9.980 (2) Å | µ = 0.23 mm−1 |
| c = 10.175 (2) Å | T = 298 (2) K |
| α = 74.600 (17)º | 0.5 × 0.5 × 0.25 mm |
| β = 70.575 (16)º |
| Stoe IPDSII diffractometer | 3801 independent reflections |
| Absorption correction: numerical shape of crystal determined optically [PROGRAM NAME? reference? | 3493 reflections with I > 2σ(I) |
| Tmin = 0.889, Tmax = 0.949 | Rint = 0.045 |
| 8123 measured reflections |
| R[F2 > 2σ(F2)] = 0.046 | 208 parameters |
| wR(F2) = 0.126 | H-atom parameters constrained |
| S = 1.04 | Δρmax = 0.25 e Å−3 |
| 3801 reflections | Δρmin = −0.19 e Å−3 |
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. |
| x | y | z | Uiso*/Ueq | ||
| Cl1 | 0.59962 (5) | 0.96565 (4) | 0.17975 (4) | 0.06276 (16) | |
| N1 | 0.51106 (12) | 0.54812 (13) | 0.69575 (11) | 0.0391 (2) | |
| C1 | 0.53821 (13) | 0.64045 (14) | 0.57445 (12) | 0.0354 (2) | |
| C2 | 0.42557 (15) | 0.79582 (15) | 0.56208 (15) | 0.0440 (3) | |
| H2 | 0.3377 | 0.8313 | 0.6366 | 0.053* | |
| C3 | 0.44417 (16) | 0.89348 (15) | 0.44312 (16) | 0.0462 (3) | |
| H3 | 0.3693 | 0.9949 | 0.4354 | 0.055* | |
| C4 | 0.57823 (15) | 0.83909 (14) | 0.33177 (14) | 0.0418 (3) | |
| C5 | 0.69071 (14) | 0.69125 (14) | 0.33901 (13) | 0.0392 (3) | |
| H5 | 0.7787 | 0.659 | 0.2639 | 0.047* | |
| C6 | 0.67271 (13) | 0.58733 (13) | 0.46148 (12) | 0.0333 (2) | |
| C7 | 0.78256 (13) | 0.43037 (13) | 0.47776 (12) | 0.0339 (2) | |
| C8 | 0.75403 (14) | 0.33702 (14) | 0.60027 (12) | 0.0357 (2) | |
| C9 | 0.86347 (17) | 0.16885 (15) | 0.62161 (14) | 0.0456 (3) | |
| H9A | 0.9111 | 0.1313 | 0.531 | 0.055* | |
| H9B | 0.8003 | 0.1139 | 0.6796 | 0.055* | |
| C10 | 0.99695 (16) | 0.13077 (18) | 0.69016 (16) | 0.0542 (4) | |
| H10A | 1.0455 | 0.0207 | 0.7167 | 0.065* | |
| H10B | 1.0777 | 0.1584 | 0.62 | 0.065* | |
| C11 | 0.94953 (18) | 0.2078 (2) | 0.81886 (16) | 0.0549 (4) | |
| H11A | 0.9085 | 0.3178 | 0.7909 | 0.066* | |
| H11B | 1.0445 | 0.1765 | 0.8501 | 0.066* | |
| C12 | 0.82614 (19) | 0.17430 (19) | 0.94328 (16) | 0.0553 (4) | |
| H12A | 0.8568 | 0.1606 | 1.0289 | 0.066* | |
| H12B | 0.8289 | 0.078 | 0.936 | 0.066* | |
| C13 | 0.65535 (18) | 0.29655 (18) | 0.95684 (14) | 0.0510 (3) | |
| H13A | 0.6551 | 0.3948 | 0.9529 | 0.061* | |
| H13B | 0.5927 | 0.2748 | 1.0491 | 0.061* | |
| C14 | 0.57222 (16) | 0.31198 (17) | 0.84728 (14) | 0.0470 (3) | |
| H14A | 0.5988 | 0.2101 | 0.8307 | 0.056* | |
| H14B | 0.4582 | 0.3605 | 0.8855 | 0.056* | |
| C15 | 0.61401 (13) | 0.40276 (14) | 0.70838 (12) | 0.0370 (3) | |
| C16 | 0.92569 (13) | 0.37293 (13) | 0.35925 (12) | 0.0359 (2) | |
| C17 | 0.91195 (17) | 0.34403 (19) | 0.23968 (14) | 0.0498 (3) | |
| H17 | 0.8139 | 0.3575 | 0.2335 | 0.06* | |
| C18 | 1.0449 (2) | 0.2949 (2) | 0.12879 (17) | 0.0655 (5) | |
| H18 | 1.0355 | 0.2746 | 0.0489 | 0.079* | |
| C19 | 1.1906 (2) | 0.2758 (2) | 0.13600 (18) | 0.0631 (4) | |
| H19 | 1.2792 | 0.2421 | 0.0617 | 0.076* | |
| C20 | 1.20421 (17) | 0.30678 (19) | 0.25315 (18) | 0.0564 (4) | |
| H20 | 1.302 | 0.2955 | 0.2578 | 0.068* | |
| C21 | 1.07270 (15) | 0.35483 (16) | 0.36480 (15) | 0.0453 (3) | |
| H21 | 1.083 | 0.3752 | 0.4442 | 0.054* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0600 (3) | 0.0434 (2) | 0.0641 (3) | −0.01716 (17) | −0.01096 (18) | 0.01044 (16) |
| N1 | 0.0288 (5) | 0.0426 (5) | 0.0396 (5) | −0.0107 (4) | −0.0059 (4) | −0.0076 (4) |
| C1 | 0.0271 (5) | 0.0369 (6) | 0.0400 (6) | −0.0093 (4) | −0.0084 (4) | −0.0094 (4) |
| C2 | 0.0304 (6) | 0.0392 (6) | 0.0524 (7) | −0.0063 (5) | −0.0053 (5) | −0.0130 (5) |
| C3 | 0.0367 (6) | 0.0334 (6) | 0.0607 (8) | −0.0071 (5) | −0.0131 (6) | −0.0078 (5) |
| C4 | 0.0396 (6) | 0.0357 (6) | 0.0486 (7) | −0.0157 (5) | −0.0132 (5) | −0.0006 (5) |
| C5 | 0.0327 (6) | 0.0376 (6) | 0.0426 (6) | −0.0123 (5) | −0.0068 (5) | −0.0059 (5) |
| C6 | 0.0268 (5) | 0.0346 (5) | 0.0377 (5) | −0.0102 (4) | −0.0084 (4) | −0.0083 (4) |
| C7 | 0.0277 (5) | 0.0358 (6) | 0.0366 (5) | −0.0095 (4) | −0.0080 (4) | −0.0096 (4) |
| C8 | 0.0318 (5) | 0.0346 (6) | 0.0391 (6) | −0.0103 (4) | −0.0104 (4) | −0.0074 (4) |
| C9 | 0.0475 (7) | 0.0333 (6) | 0.0455 (7) | −0.0086 (5) | −0.0103 (5) | −0.0065 (5) |
| C10 | 0.0372 (7) | 0.0478 (7) | 0.0542 (8) | −0.0030 (6) | −0.0116 (6) | 0.0008 (6) |
| C11 | 0.0457 (7) | 0.0622 (9) | 0.0552 (8) | −0.0218 (7) | −0.0207 (6) | 0.0034 (7) |
| C12 | 0.0548 (8) | 0.0573 (9) | 0.0470 (7) | −0.0206 (7) | −0.0186 (6) | 0.0057 (6) |
| C13 | 0.0531 (8) | 0.0526 (8) | 0.0366 (6) | −0.0188 (6) | −0.0069 (5) | −0.0013 (5) |
| C14 | 0.0372 (6) | 0.0509 (7) | 0.0463 (7) | −0.0197 (6) | −0.0053 (5) | −0.0001 (6) |
| C15 | 0.0301 (5) | 0.0413 (6) | 0.0387 (6) | −0.0142 (5) | −0.0091 (4) | −0.0050 (5) |
| C16 | 0.0308 (5) | 0.0325 (5) | 0.0378 (6) | −0.0083 (4) | −0.0052 (4) | −0.0085 (4) |
| C17 | 0.0420 (7) | 0.0655 (9) | 0.0450 (7) | −0.0231 (6) | −0.0054 (5) | −0.0178 (6) |
| C18 | 0.0635 (10) | 0.0914 (13) | 0.0468 (8) | −0.0362 (9) | 0.0029 (7) | −0.0309 (8) |
| C19 | 0.0472 (8) | 0.0739 (11) | 0.0574 (9) | −0.0243 (8) | 0.0123 (7) | −0.0265 (8) |
| C20 | 0.0323 (6) | 0.0617 (9) | 0.0695 (9) | −0.0167 (6) | −0.0022 (6) | −0.0190 (7) |
| C21 | 0.0348 (6) | 0.0471 (7) | 0.0513 (7) | −0.0118 (5) | −0.0087 (5) | −0.0152 (6) |
| C1—N1 | 1.3612 (16) | C11—H11A | 0.97 |
| C1—C6 | 1.4153 (16) | C11—H11B | 0.97 |
| C1—C2 | 1.4194 (17) | C12—C13 | 1.526 (2) |
| C2—C3 | 1.358 (2) | C12—H12A | 0.97 |
| C2—H2 | 0.93 | C12—H12B | 0.97 |
| C3—C4 | 1.4051 (19) | C13—C14 | 1.527 (2) |
| C3—H3 | 0.93 | C13—H13A | 0.97 |
| C4—C5 | 1.3644 (18) | C13—H13B | 0.97 |
| C4—Cl1 | 1.7405 (14) | C14—C15 | 1.5075 (18) |
| C5—C6 | 1.4143 (17) | C14—H14A | 0.97 |
| C5—H5 | 0.93 | C14—H14B | 0.97 |
| C6—C7 | 1.4255 (16) | C15—N1 | 1.3217 (17) |
| C7—C8 | 1.3777 (17) | C16—C17 | 1.3836 (18) |
| C7—C16 | 1.4969 (16) | C16—C21 | 1.3890 (18) |
| C8—C15 | 1.4353 (17) | C17—C18 | 1.390 (2) |
| C8—C9 | 1.5096 (17) | C17—H17 | 0.93 |
| C9—C10 | 1.534 (2) | C18—C19 | 1.378 (3) |
| C9—H9A | 0.97 | C18—H18 | 0.93 |
| C9—H9B | 0.97 | C19—C20 | 1.370 (2) |
| C10—C11 | 1.521 (2) | C19—H19 | 0.93 |
| C10—H10A | 0.97 | C20—C21 | 1.3857 (19) |
| C10—H10B | 0.97 | C20—H20 | 0.93 |
| C11—C12 | 1.524 (2) | C21—H21 | 0.93 |
| N1—C1—C6 | 122.66 (11) | H11A—C11—H11B | 107.4 |
| N1—C1—C2 | 117.98 (11) | C11—C12—C13 | 115.65 (13) |
| C6—C1—C2 | 119.36 (11) | C11—C12—H12A | 108.4 |
| C3—C2—C1 | 121.00 (12) | C13—C12—H12A | 108.4 |
| C3—C2—H2 | 119.5 | C11—C12—H12B | 108.4 |
| C1—C2—H2 | 119.5 | C13—C12—H12B | 108.4 |
| C2—C3—C4 | 119.00 (12) | H12A—C12—H12B | 107.4 |
| C2—C3—H3 | 120.5 | C12—C13—C14 | 116.62 (13) |
| C4—C3—H3 | 120.5 | C12—C13—H13A | 108.1 |
| C5—C4—C3 | 122.25 (12) | C14—C13—H13A | 108.1 |
| C5—C4—Cl1 | 119.37 (10) | C12—C13—H13B | 108.1 |
| C3—C4—Cl1 | 118.37 (10) | C14—C13—H13B | 108.1 |
| C4—C5—C6 | 119.61 (11) | H13A—C13—H13B | 107.3 |
| C4—C5—H5 | 120.2 | C15—C14—C13 | 114.79 (11) |
| C6—C5—H5 | 120.2 | C15—C14—H14A | 108.6 |
| C5—C6—C1 | 118.77 (11) | C13—C14—H14A | 108.6 |
| C5—C6—C7 | 123.61 (10) | C15—C14—H14B | 108.6 |
| C1—C6—C7 | 117.63 (11) | C13—C14—H14B | 108.6 |
| C8—C7—C6 | 119.53 (10) | H14A—C14—H14B | 107.5 |
| C8—C7—C16 | 122.32 (10) | N1—C15—C8 | 123.17 (11) |
| C6—C7—C16 | 118.15 (10) | N1—C15—C14 | 114.02 (11) |
| C7—C8—C15 | 118.28 (11) | C8—C15—C14 | 122.80 (11) |
| C7—C8—C9 | 121.86 (11) | C17—C16—C21 | 118.98 (11) |
| C15—C8—C9 | 119.85 (11) | C17—C16—C7 | 120.43 (11) |
| C8—C9—C10 | 115.07 (12) | C21—C16—C7 | 120.52 (11) |
| C8—C9—H9A | 108.5 | C16—C17—C18 | 119.87 (13) |
| C10—C9—H9A | 108.5 | C16—C17—H17 | 120.1 |
| C8—C9—H9B | 108.5 | C18—C17—H17 | 120.1 |
| C10—C9—H9B | 108.5 | C19—C18—C17 | 120.65 (15) |
| H9A—C9—H9B | 107.5 | C19—C18—H18 | 119.7 |
| C11—C10—C9 | 116.56 (12) | C17—C18—H18 | 119.7 |
| C11—C10—H10A | 108.2 | C20—C19—C18 | 119.70 (13) |
| C9—C10—H10A | 108.2 | C20—C19—H19 | 120.2 |
| C11—C10—H10B | 108.2 | C18—C19—H19 | 120.1 |
| C9—C10—H10B | 108.2 | C19—C20—C21 | 120.16 (14) |
| H10A—C10—H10B | 107.3 | C19—C20—H20 | 119.9 |
| C10—C11—C12 | 116.04 (14) | C21—C20—H20 | 119.9 |
| C10—C11—H11A | 108.3 | C20—C21—C16 | 120.63 (13) |
| C12—C11—H11A | 108.3 | C20—C21—H21 | 119.7 |
| C10—C11—H11B | 108.3 | C16—C21—H21 | 119.7 |
| C12—C11—H11B | 108.3 | C15—N1—C1 | 118.73 (10) |
| N1—C1—C2—C3 | −178.99 (12) | C10—C11—C12—C13 | −98.63 (17) |
| C6—C1—C2—C3 | 0.70 (19) | C11—C12—C13—C14 | 70.55 (19) |
| C1—C2—C3—C4 | −0.6 (2) | C12—C13—C14—C15 | −80.42 (17) |
| C2—C3—C4—C5 | 0.0 (2) | C7—C8—C15—N1 | 0.29 (18) |
| C2—C3—C4—Cl1 | 179.69 (11) | C9—C8—C15—N1 | −178.45 (11) |
| C3—C4—C5—C6 | 0.7 (2) | C7—C8—C15—C14 | −179.14 (11) |
| Cl1—C4—C5—C6 | −179.07 (9) | C9—C8—C15—C14 | 2.13 (18) |
| C4—C5—C6—C1 | −0.59 (18) | C13—C14—C15—N1 | −96.60 (14) |
| C4—C5—C6—C7 | 178.98 (11) | C13—C14—C15—C8 | 82.88 (16) |
| N1—C1—C6—C5 | 179.60 (10) | C8—C7—C16—C17 | 103.88 (15) |
| C2—C1—C6—C5 | −0.07 (17) | C6—C7—C16—C17 | −75.90 (16) |
| N1—C1—C6—C7 | 0.00 (17) | C8—C7—C16—C21 | −79.21 (16) |
| C2—C1—C6—C7 | −179.67 (11) | C6—C7—C16—C21 | 101.02 (14) |
| C5—C6—C7—C8 | −179.10 (11) | C21—C16—C17—C18 | 1.2 (2) |
| C1—C6—C7—C8 | 0.48 (16) | C7—C16—C17—C18 | 178.19 (15) |
| C5—C6—C7—C16 | 0.69 (17) | C16—C17—C18—C19 | −0.6 (3) |
| C1—C6—C7—C16 | −179.74 (10) | C17—C18—C19—C20 | −0.5 (3) |
| C6—C7—C8—C15 | −0.62 (17) | C18—C19—C20—C21 | 1.0 (3) |
| C16—C7—C8—C15 | 179.61 (10) | C19—C20—C21—C16 | −0.3 (2) |
| C6—C7—C8—C9 | 178.09 (11) | C17—C16—C21—C20 | −0.8 (2) |
| C16—C7—C8—C9 | −1.68 (18) | C7—C16—C21—C20 | −177.74 (13) |
| C7—C8—C9—C10 | 91.27 (15) | C8—C15—N1—C1 | 0.19 (18) |
| C15—C8—C9—C10 | −90.04 (15) | C14—C15—N1—C1 | 179.66 (10) |
| C8—C9—C10—C11 | 46.24 (18) | C6—C1—N1—C15 | −0.33 (18) |
| C9—C10—C11—C12 | 59.62 (18) | C2—C1—N1—C15 | 179.34 (11) |
I am grateful to the Islamic Azad University, Dorood Branch, for financial support.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Doube, D., Blouin, M., Brideau, C., Chan, C., Desmarais, S., Eithier, D., Falgueyert, J. P., Friesen, R. W., Girrard, M., Girrard, J., Tagari, P. & Yang, R. N. (1998). Bioorg. Med. Chem. Lett. 8, 1255–1260.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Kalluraya, B. & Sreenivasa, S. (1998). Farmaco, 53, 399–404.
Maguire, M. P., Sheets, K. R., Mevety, K., Spada, A. P. & Ziberstein, A. (1994). J. Med. Chem. 37, 2129–2137.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Stoe & Cie (2002). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.
Quinoline nucleus is a backbone of many natural products and pharmacologicallly significant compounds displaying a broad range of biological activities and many functionalized quinolines are widely used as antimalarial, antiasthmatic, antiinflamatory, antibacterial, antihypertensive and tyrosine kinase PDGF-RTK inhibiting agents (Kalluraya & Sreenivasa, 1998; Doube et al., 1998; Maguire et al., 1994). We report herein the synthesis and crystal structure of the title compound, (I).
In the molecule of the title compound, (I), (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6), B (N1/C1/C6-C8/C15) and C (C16-C21) are, of course, planar, and they are oriented at dihedral angles of A/B = 0.88 (3)°, A/C = 76.76 (4)° and B/C = 77.64 (3)°. So, rings A and B are also nearly coplanar. The dihedral angle between the coplanar ring system and ring C is 77.21 (3)°.
In the crystal structure, the weak π–π interactions between the two adjacent A rings and A and B rings, with centroid-centroid distances of 3.7414 (11) Å and 3.8633 (12) Å, may be effective in the stabilization of the structure (Fig. 2).