In the title compound, C
26H
22N
2O
2S, the tetrahydropyridine ring has a conformation intermediate between half-chair and sofa. The tetrahydroquinoline mean plane makes a dihedral angle of 73.3 (1)° with the cyclopentene ring, which adopts an envelope conformation, and an angle of 45.45 (4)° with the indole best plane. The dihedral angle between the benzene and pyrrole rings is 2.6 (1)°. The orientations of the phenyl ring on the sulfonyl group and of the indole are governed by weak C—H
O interactions. The packing of the molecule in the solid state is stabilized by C—H
O and C—H
N hydrogen bonds.
Supporting information
To a solution of 4-phenylsulfonyl-3-[N-phenylformimidoyl]-indol (0.648 g,
0.018 mol) and cyclopentadiene (0.237 g, 0.036 mol) in acetonitrile (10 ml)
protected by a guard tube was added indium trichloride (0.081 g, 20 mol%) and
the mixture was stirred at room temperature for 30 min. Water (20 ml) was
added to the reaction mixture, which was then extracted with chloroform (3
× 10 ml), washed with brine (10 ml), dried over anhydrous sodium sulfate
and concentrated under reduced pressure. The crude product was purified by
column chromotography using silica gel (60–120 mesh) and eluted with
petroleum ether:ethyl acetate (90:10) to afford compound (I) (yield 83%).
All H atoms were geometrically fixed and allowed to ride on the corresponding
non-H atoms.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983b, 1995).
4-[1-(phenylsulfonyl)indol-3-yl]-3a,4,5,9
b-tetrahydro-3
H-cyclopenta[
c] quinoline
top
Crystal data top
C26H22N2O2S | F(000) = 896 |
Mr = 426.52 | Dx = 1.264 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.4515 (2) Å | Cell parameters from 8192 reflections |
b = 8.6572 (1) Å | θ = 1.5–28.3° |
c = 22.6109 (4) Å | µ = 0.17 mm−1 |
β = 90.864 (1)° | T = 293 K |
V = 2241.34 (6) Å3 | Block, pale yellow |
Z = 4 | 0.48 × 0.34 × 0.28 mm |
Data collection top
Siemens SMART CCD area detector diffractometer | 3542 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 28.3°, θmin = 1.8° |
ω scans | h = −9→15 |
14562 measured reflections | k = −11→10 |
5435 independent reflections | l = −29→29 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.02 | Calculated w = 1/[σ2(Fo2) + (0.0586P)2 + 0.9637P] where P = (Fo2 + 2Fc2)/3 |
5435 reflections | (Δ/σ)max = 0.003 |
280 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
Crystal data top
C26H22N2O2S | V = 2241.34 (6) Å3 |
Mr = 426.52 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.4515 (2) Å | µ = 0.17 mm−1 |
b = 8.6572 (1) Å | T = 293 K |
c = 22.6109 (4) Å | 0.48 × 0.34 × 0.28 mm |
β = 90.864 (1)° | |
Data collection top
Siemens SMART CCD area detector diffractometer | 3542 reflections with I > 2σ(I) |
14562 measured reflections | Rint = 0.040 |
5435 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.50 e Å−3 |
5435 reflections | Δρmin = −0.49 e Å−3 |
280 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S22 | 0.09906 (5) | 0.89569 (7) | 0.14903 (2) | 0.04548 (17) | |
N1 | 0.17275 (15) | 0.7366 (2) | −0.08121 (7) | 0.0405 (4) | |
H1 | 0.1259 | 0.6944 | −0.0566 | 0.049* | |
C1 | 0.21563 (17) | 0.6527 (2) | −0.12960 (9) | 0.0373 (5) | |
C2 | 0.1558 (2) | 0.5209 (3) | −0.14855 (10) | 0.0458 (5) | |
H2 | 0.0872 | 0.4920 | −0.1300 | 0.055* | |
C3 | 0.1979 (2) | 0.4323 (3) | −0.19494 (11) | 0.0558 (6) | |
H3 | 0.1576 | 0.3442 | −0.2070 | 0.067* | |
C4 | 0.2997 (2) | 0.4745 (3) | −0.22330 (11) | 0.0587 (7) | |
H4 | 0.3270 | 0.4166 | −0.2549 | 0.070* | |
C5 | 0.3595 (2) | 0.6031 (3) | −0.20410 (11) | 0.0555 (6) | |
H5 | 0.4281 | 0.6307 | −0.2229 | 0.067* | |
C6 | 0.32030 (19) | 0.6942 (3) | −0.15712 (9) | 0.0435 (5) | |
C7 | 0.3912 (2) | 0.8324 (3) | −0.13577 (12) | 0.0587 (7) | |
H7 | 0.3958 | 0.9108 | −0.1669 | 0.070* | |
C8 | 0.5118 (2) | 0.7827 (4) | −0.11617 (19) | 0.0909 (11) | |
H8 | 0.5718 | 0.7589 | −0.1419 | 0.109* | |
C9 | 0.5215 (2) | 0.7773 (5) | −0.05875 (19) | 0.0963 (12) | |
H9 | 0.5896 | 0.7479 | −0.0388 | 0.116* | |
C10 | 0.4104 (2) | 0.8237 (4) | −0.02762 (13) | 0.0692 (8) | |
H10A | 0.4265 | 0.8935 | 0.0051 | 0.083* | |
H10B | 0.3683 | 0.7344 | −0.0133 | 0.083* | |
C11 | 0.3436 (2) | 0.9046 (3) | −0.07785 (11) | 0.0509 (6) | |
H11 | 0.3660 | 1.0138 | −0.0773 | 0.061* | |
C12 | 0.20972 (18) | 0.8964 (2) | −0.07387 (9) | 0.0388 (5) | |
H12 | 0.1747 | 0.9592 | −0.1055 | 0.047* | |
C13 | 0.16867 (17) | 0.9554 (2) | −0.01463 (9) | 0.0367 (4) | |
C14 | 0.13398 (18) | 0.8687 (2) | 0.03160 (9) | 0.0402 (5) | |
H14 | 0.1268 | 0.7617 | 0.0312 | 0.048* | |
N15 | 0.11016 (15) | 0.9643 (2) | 0.08083 (7) | 0.0410 (4) | |
C16 | 0.13558 (17) | 1.1183 (2) | 0.06448 (9) | 0.0376 (4) | |
C17 | 0.1286 (2) | 1.2546 (3) | 0.09697 (11) | 0.0487 (6) | |
H17 | 0.1086 | 1.2545 | 0.1367 | 0.058* | |
C18 | 0.1527 (2) | 1.3904 (3) | 0.06718 (13) | 0.0598 (7) | |
H18 | 0.1488 | 1.4837 | 0.0874 | 0.072* | |
C19 | 0.1828 (2) | 1.3911 (3) | 0.00749 (13) | 0.0614 (7) | |
H19 | 0.1976 | 1.4847 | −0.0111 | 0.074* | |
C20 | 0.1910 (2) | 1.2553 (3) | −0.02437 (11) | 0.0503 (6) | |
H20 | 0.2110 | 1.2567 | −0.0641 | 0.060* | |
C21 | 0.16843 (17) | 1.1156 (2) | 0.00449 (9) | 0.0377 (4) | |
O23 | 0.05471 (16) | 0.7424 (2) | 0.14217 (8) | 0.0607 (5) | |
O24 | 0.03703 (16) | 1.0085 (2) | 0.18261 (8) | 0.0651 (5) | |
C25 | 0.2432 (2) | 0.8834 (3) | 0.17661 (9) | 0.0454 (5) | |
C26 | 0.3183 (2) | 0.7746 (3) | 0.15305 (13) | 0.0637 (7) | |
H26 | 0.2942 | 0.7123 | 0.1217 | 0.076* | |
C27 | 0.4306 (3) | 0.7602 (4) | 0.17707 (15) | 0.0758 (8) | |
H27 | 0.4818 | 0.6876 | 0.1618 | 0.091* | |
C28 | 0.4654 (3) | 0.8522 (4) | 0.22296 (15) | 0.0769 (9) | |
H28 | 0.5400 | 0.8410 | 0.2391 | 0.092* | |
C29 | 0.3917 (3) | 0.9608 (4) | 0.24543 (14) | 0.0811 (9) | |
H29 | 0.4173 | 1.0240 | 0.2763 | 0.097* | |
C30 | 0.2787 (3) | 0.9782 (3) | 0.22280 (11) | 0.0645 (7) | |
H30 | 0.2284 | 1.0516 | 0.2383 | 0.077* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S22 | 0.0463 (3) | 0.0502 (3) | 0.0401 (3) | −0.0093 (3) | 0.0072 (2) | 0.0003 (2) |
N1 | 0.0380 (9) | 0.0444 (10) | 0.0395 (9) | −0.0096 (8) | 0.0070 (7) | −0.0065 (8) |
C1 | 0.0359 (11) | 0.0421 (11) | 0.0338 (10) | 0.0011 (9) | −0.0032 (8) | 0.0005 (9) |
C2 | 0.0419 (12) | 0.0507 (13) | 0.0446 (12) | −0.0025 (10) | −0.0038 (9) | −0.0064 (10) |
C3 | 0.0636 (16) | 0.0520 (14) | 0.0517 (14) | 0.0033 (12) | −0.0091 (12) | −0.0142 (11) |
C4 | 0.0683 (17) | 0.0633 (17) | 0.0447 (13) | 0.0149 (14) | 0.0021 (12) | −0.0111 (12) |
C5 | 0.0540 (14) | 0.0652 (17) | 0.0477 (13) | 0.0087 (13) | 0.0134 (11) | 0.0035 (12) |
C6 | 0.0414 (12) | 0.0486 (13) | 0.0405 (11) | 0.0011 (10) | 0.0046 (9) | 0.0048 (10) |
C7 | 0.0491 (14) | 0.0608 (16) | 0.0669 (16) | −0.0120 (12) | 0.0206 (12) | −0.0031 (13) |
C8 | 0.0386 (15) | 0.117 (3) | 0.117 (3) | −0.0157 (17) | 0.0149 (16) | −0.038 (2) |
C9 | 0.0362 (15) | 0.130 (3) | 0.122 (3) | 0.0020 (17) | −0.0197 (17) | −0.034 (3) |
C10 | 0.0417 (14) | 0.087 (2) | 0.0782 (19) | −0.0050 (14) | −0.0117 (12) | −0.0167 (16) |
C11 | 0.0443 (13) | 0.0465 (13) | 0.0621 (15) | −0.0144 (11) | 0.0070 (10) | −0.0058 (11) |
C12 | 0.0397 (11) | 0.0376 (11) | 0.0391 (11) | −0.0012 (9) | −0.0004 (8) | 0.0001 (9) |
C13 | 0.0332 (10) | 0.0366 (10) | 0.0402 (11) | −0.0018 (9) | −0.0042 (8) | −0.0003 (9) |
C14 | 0.0456 (12) | 0.0347 (11) | 0.0401 (11) | −0.0029 (9) | −0.0017 (9) | −0.0046 (9) |
N15 | 0.0470 (10) | 0.0376 (9) | 0.0382 (9) | −0.0048 (8) | −0.0002 (8) | −0.0029 (8) |
C16 | 0.0334 (10) | 0.0336 (11) | 0.0456 (11) | −0.0001 (8) | −0.0048 (8) | −0.0009 (9) |
C17 | 0.0494 (13) | 0.0414 (13) | 0.0551 (14) | 0.0037 (10) | −0.0033 (10) | −0.0099 (11) |
C18 | 0.0648 (16) | 0.0350 (13) | 0.0793 (19) | 0.0038 (11) | −0.0043 (13) | −0.0110 (13) |
C19 | 0.0693 (17) | 0.0336 (12) | 0.0811 (19) | 0.0003 (12) | −0.0042 (14) | 0.0083 (13) |
C20 | 0.0537 (14) | 0.0413 (13) | 0.0558 (14) | 0.0006 (11) | −0.0026 (11) | 0.0084 (11) |
C21 | 0.0336 (10) | 0.0343 (11) | 0.0449 (11) | 0.0007 (9) | −0.0064 (8) | 0.0018 (9) |
O23 | 0.0629 (11) | 0.0585 (11) | 0.0607 (11) | −0.0264 (9) | 0.0002 (8) | 0.0088 (9) |
O24 | 0.0638 (11) | 0.0788 (13) | 0.0535 (10) | 0.0035 (10) | 0.0217 (9) | −0.0084 (9) |
C25 | 0.0514 (13) | 0.0461 (13) | 0.0386 (11) | −0.0091 (11) | −0.0018 (9) | 0.0051 (10) |
C26 | 0.0611 (16) | 0.0642 (17) | 0.0655 (17) | 0.0012 (14) | −0.0096 (13) | −0.0089 (14) |
C27 | 0.0642 (18) | 0.0701 (19) | 0.093 (2) | 0.0085 (15) | −0.0094 (16) | 0.0000 (17) |
C28 | 0.0699 (19) | 0.073 (2) | 0.087 (2) | −0.0109 (17) | −0.0268 (16) | 0.0141 (17) |
C29 | 0.097 (2) | 0.080 (2) | 0.0653 (19) | −0.018 (2) | −0.0340 (17) | −0.0033 (16) |
C30 | 0.0802 (19) | 0.0637 (17) | 0.0491 (14) | −0.0035 (15) | −0.0099 (13) | −0.0071 (13) |
Geometric parameters (Å, º) top
S22—O23 | 1.429 (2) | C11—H11 | 0.9800 |
S22—O24 | 1.432 (2) | C12—C13 | 1.515 (3) |
S22—N15 | 1.659 (2) | C12—H12 | 0.9800 |
S22—C25 | 1.758 (2) | C13—C14 | 1.352 (3) |
N1—C1 | 1.408 (3) | C13—C21 | 1.452 (3) |
N1—C12 | 1.456 (3) | C14—N15 | 1.417 (3) |
N1—H1 | 0.8600 | C14—H14 | 0.9300 |
C1—C2 | 1.394 (3) | N15—C16 | 1.415 (3) |
C1—C6 | 1.406 (3) | C16—C17 | 1.393 (3) |
C2—C3 | 1.392 (3) | C16—C21 | 1.413 (3) |
C2—H2 | 0.9300 | C17—C18 | 1.385 (3) |
C3—C4 | 1.387 (4) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—C19 | 1.398 (4) |
C4—C5 | 1.374 (4) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—C20 | 1.383 (3) |
C5—C6 | 1.402 (3) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C20—C21 | 1.400 (3) |
C6—C7 | 1.521 (3) | C20—H20 | 0.9300 |
C7—C8 | 1.506 (4) | C25—C30 | 1.385 (3) |
C7—C11 | 1.557 (3) | C25—C26 | 1.388 (3) |
C7—H7 | 0.9800 | C26—C27 | 1.393 (4) |
C8—C9 | 1.302 (5) | C26—H26 | 0.9300 |
C8—H8 | 0.9300 | C27—C28 | 1.363 (4) |
C9—C10 | 1.518 (4) | C27—H27 | 0.9300 |
C9—H9 | 0.9300 | C28—C29 | 1.366 (4) |
C10—C11 | 1.529 (4) | C28—H28 | 0.9300 |
C10—H10A | 0.9700 | C29—C30 | 1.392 (4) |
C10—H10B | 0.9700 | C29—H29 | 0.9300 |
C11—C12 | 1.539 (3) | C30—H30 | 0.9300 |
| | | |
O23—S22—O24 | 120.9 (1) | N1—C12—C13 | 109.1 (2) |
O23—S22—N15 | 105.3 (1) | N1—C12—C11 | 109.0 (2) |
O24—S22—N15 | 107.1 (1) | C13—C12—C11 | 111.0 (2) |
O23—S22—C25 | 108.2 (1) | N1—C12—H12 | 109.2 |
O24—S22—C25 | 108.9 (1) | C13—C12—H12 | 109.2 |
N15—S22—C25 | 105.5 (1) | C11—C12—H12 | 109.2 |
C1—N1—C12 | 118.3 (2) | C14—C13—C21 | 107.4 (2) |
C1—N1—H1 | 120.8 | C14—C13—C12 | 126.5 (2) |
C12—N1—H1 | 120.8 | C21—C13—C12 | 126.0 (2) |
C2—C1—C6 | 119.4 (2) | C13—C14—N15 | 110.22 (18) |
C2—C1—N1 | 119.0 (2) | C13—C14—H14 | 124.9 |
C6—C1—N1 | 121.5 (2) | N15—C14—H14 | 124.9 |
C3—C2—C1 | 120.6 (2) | C16—N15—C14 | 107.6 (2) |
C3—C2—H2 | 119.7 | C16—N15—S22 | 126.8 (1) |
C1—C2—H2 | 119.7 | C14—N15—S22 | 122.7 (2) |
C4—C3—C2 | 120.4 (2) | C17—C16—C21 | 122.6 (2) |
C4—C3—H3 | 119.8 | C17—C16—N15 | 130.3 (2) |
C2—C3—H3 | 119.8 | C21—C16—N15 | 107.1 (2) |
C5—C4—C3 | 119.0 (2) | C18—C17—C16 | 116.7 (2) |
C5—C4—H4 | 120.5 | C18—C17—H17 | 121.7 |
C3—C4—H4 | 120.5 | C16—C17—H17 | 121.7 |
C4—C5—C6 | 122.1 (2) | C17—C18—C19 | 121.8 (2) |
C4—C5—H5 | 118.9 | C17—C18—H18 | 119.1 |
C6—C5—H5 | 118.9 | C19—C18—H18 | 119.1 |
C5—C6—C1 | 118.5 (2) | C20—C19—C18 | 121.2 (2) |
C5—C6—C7 | 120.5 (2) | C20—C19—H19 | 119.4 |
C1—C6—C7 | 121.0 (2) | C18—C19—H19 | 119.4 |
C8—C7—C6 | 110.6 (2) | C19—C20—C21 | 118.5 (2) |
C8—C7—C11 | 101.4 (2) | C19—C20—H20 | 120.7 |
C6—C7—C11 | 113.0 (2) | C21—C20—H20 | 120.7 |
C8—C7—H7 | 110.5 | C20—C21—C16 | 119.1 (2) |
C6—C7—H7 | 110.5 | C20—C21—C13 | 133.2 (2) |
C11—C7—H7 | 110.5 | C16—C21—C13 | 107.7 (2) |
C9—C8—C7 | 111.6 (3) | C30—C25—C26 | 121.0 (2) |
C9—C8—H8 | 124.2 | C30—C25—S22 | 119.7 (2) |
C7—C8—H8 | 124.2 | C26—C25—S22 | 119.3 (2) |
C8—C9—C10 | 113.2 (3) | C25—C26—C27 | 119.0 (3) |
C8—C9—H9 | 123.4 | C25—C26—H26 | 120.5 |
C10—C9—H9 | 123.4 | C27—C26—H26 | 120.5 |
C9—C10—C11 | 101.0 (2) | C28—C27—C26 | 120.1 (3) |
C9—C10—H10A | 111.6 | C28—C27—H27 | 119.9 |
C11—C10—H10A | 111.6 | C26—C27—H27 | 119.9 |
C9—C10—H10B | 111.6 | C27—C28—C29 | 120.7 (3) |
C11—C10—H10B | 111.6 | C27—C28—H28 | 119.7 |
H10A—C10—H10B | 109.4 | C29—C28—H28 | 119.7 |
C10—C11—C12 | 115.0 (2) | C28—C29—C30 | 120.9 (3) |
C10—C11—C7 | 105.3 (2) | C28—C29—H29 | 119.5 |
C12—C11—C7 | 113.1 (2) | C30—C29—H29 | 119.5 |
C10—C11—H11 | 107.7 | C25—C30—C29 | 118.3 (3) |
C12—C11—H11 | 107.7 | C25—C30—H30 | 120.9 |
C7—C11—H11 | 107.7 | C29—C30—H30 | 120.9 |
| | | |
C12—N1—C1—C2 | −159.9 (2) | C13—C14—N15—S22 | −163.8 (2) |
C12—N1—C1—C6 | 23.4 (3) | O23—S22—N15—C16 | 171.2 (2) |
C6—C1—C2—C3 | −1.1 (3) | O24—S22—N15—C16 | 41.3 (2) |
N1—C1—C2—C3 | −177.8 (2) | C25—S22—N15—C16 | −74.5 (2) |
C1—C2—C3—C4 | −0.5 (4) | O23—S22—N15—C14 | −30.8 (2) |
C2—C3—C4—C5 | 1.4 (4) | O24—S22—N15—C14 | −160.6 (2) |
C3—C4—C5—C6 | −0.7 (4) | C25—S22—N15—C14 | 83.6 (2) |
C4—C5—C6—C1 | −0.8 (4) | C14—N15—C16—C17 | −179.0 (2) |
C4—C5—C6—C7 | 177.8 (2) | S22—N15—C16—C17 | −18.2 (3) |
C2—C1—C6—C5 | 1.7 (3) | C14—N15—C16—C21 | 3.1 (2) |
N1—C1—C6—C5 | 178.4 (2) | S22—N15—C16—C21 | 163.9 (2) |
C2—C1—C6—C7 | −177.0 (2) | C21—C16—C17—C18 | 1.6 (3) |
N1—C1—C6—C7 | −0.3 (3) | N15—C16—C17—C18 | −176.1 (2) |
C5—C6—C7—C8 | −58.8 (3) | C16—C17—C18—C19 | 0.0 (4) |
C1—C6—C7—C8 | 119.9 (3) | C17—C18—C19—C20 | −0.7 (4) |
C5—C6—C7—C11 | −171.7 (2) | C18—C19—C20—C21 | 0.0 (4) |
C1—C6—C7—C11 | 7.0 (3) | C19—C20—C21—C16 | 1.5 (3) |
C6—C7—C8—C9 | −103.0 (3) | C19—C20—C21—C13 | 179.9 (2) |
C11—C7—C8—C9 | 17.1 (4) | C17—C16—C21—C20 | −2.3 (3) |
C7—C8—C9—C10 | −0.6 (5) | N15—C16—C21—C20 | 175.8 (2) |
C8—C9—C10—C11 | −16.4 (4) | C17—C16—C21—C13 | 178.9 (2) |
C9—C10—C11—C12 | 150.9 (2) | N15—C16—C21—C13 | −3.0 (2) |
C9—C10—C11—C7 | 25.7 (3) | C14—C13—C21—C20 | −176.8 (2) |
C8—C7—C11—C10 | −26.3 (3) | C12—C13—C21—C20 | 7.7 (4) |
C6—C7—C11—C10 | 92.0 (2) | C14—C13—C21—C16 | 1.8 (2) |
C8—C7—C11—C12 | −152.7 (2) | C12—C13—C21—C16 | −173.7 (2) |
C6—C7—C11—C12 | −34.4 (3) | O23—S22—C25—C30 | −134.4 (2) |
C1—N1—C12—C13 | −171.4 (2) | O24—S22—C25—C30 | −1.3 (2) |
C1—N1—C12—C11 | −50.0 (2) | N15—S22—C25—C30 | 113.3 (2) |
C10—C11—C12—N1 | −66.1 (2) | O23—S22—C25—C26 | 43.2 (2) |
C7—C11—C12—N1 | 54.9 (3) | O24—S22—C25—C26 | 176.3 (2) |
C10—C11—C12—C13 | 54.1 (3) | N15—S22—C25—C26 | −69.0 (2) |
C7—C11—C12—C13 | 175.1 (2) | C30—C25—C26—C27 | 0.8 (4) |
N1—C12—C13—C14 | 17.7 (3) | S22—C25—C26—C27 | −176.8 (2) |
C11—C12—C13—C14 | −102.5 (2) | C25—C26—C27—C28 | −0.1 (5) |
N1—C12—C13—C21 | −167.6 (2) | C26—C27—C28—C29 | −0.9 (5) |
C11—C12—C13—C21 | 72.2 (3) | C27—C28—C29—C30 | 1.2 (5) |
C21—C13—C14—N15 | 0.2 (2) | C26—C25—C30—C29 | −0.5 (4) |
C12—C13—C14—N15 | 175.7 (2) | S22—C25—C30—C29 | 177.1 (2) |
C13—C14—N15—C16 | −2.1 (2) | C28—C29—C30—C25 | −0.5 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O24 | 0.93 | 2.51 | 3.074 (3) | 119 |
C30—H30···O24 | 0.93 | 2.54 | 2.912 (3) | 104 |
C29—H29···O23i | 0.93 | 2.66 | 3.568 (4) | 166 |
C2—H2···O23ii | 0.93 | 2.61 | 3.323 (3) | 134 |
C19—H19···N1iii | 0.93 | 2.71 | 3.602 (3) | 162 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x, −y+1, −z; (iii) x, y+1, z. |
Experimental details
Crystal data |
Chemical formula | C26H22N2O2S |
Mr | 426.52 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.4515 (2), 8.6572 (1), 22.6109 (4) |
β (°) | 90.864 (1) |
V (Å3) | 2241.34 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.17 |
Crystal size (mm) | 0.48 × 0.34 × 0.28 |
|
Data collection |
Diffractometer | Siemens SMART CCD area detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14562, 5435, 3542 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.667 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.149, 1.02 |
No. of reflections | 5435 |
No. of parameters | 280 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.50, −0.49 |
Selected geometric parameters (Å, º) topS22—O23 | 1.429 (2) | S22—O24 | 1.432 (2) |
| | | |
O23—S22—O24 | 120.9 (1) | N15—S22—C25 | 105.5 (1) |
O23—S22—N15 | 105.3 (1) | C16—N15—C14 | 107.6 (2) |
O24—S22—N15 | 107.1 (1) | C16—N15—S22 | 126.8 (1) |
O23—S22—C25 | 108.2 (1) | C14—N15—S22 | 122.7 (2) |
O24—S22—C25 | 108.9 (1) | | |
| | | |
C1—N1—C12—C13 | −171.4 (2) | N15—S22—C25—C26 | −69.0 (2) |
C7—C11—C12—C13 | 175.1 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O24 | 0.93 | 2.51 | 3.074 (3) | 119 |
C30—H30···O24 | 0.93 | 2.54 | 2.912 (3) | 104 |
C29—H29···O23i | 0.93 | 2.66 | 3.568 (4) | 166 |
C2—H2···O23ii | 0.93 | 2.61 | 3.323 (3) | 134 |
C19—H19···N1iii | 0.93 | 2.71 | 3.602 (3) | 162 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x, −y+1, −z; (iii) x, y+1, z. |
Quinolines and indoles have been of interest for many years, since a large number of natural products contain these heterocyclic nuclei, and they are found in numerous commercial products including pharmaceuticals, fragrances and dyes (Padwa et al., 1999). Tetrahydroquinoline derivatives exhibit antitumour activities (Jaton et al., 1997) and also act as potent antipsychotic agents (Norman et al., 1996), and a compound containing the tetrahydroquinoline moiety acts as an antischistosomal drug (Billings & Heidelberger, 1982). They also possess antiinflammatory (Ohnishi et al., 1981), antiamoebic (Bailey et al., 1979), antiulcer (Uchida et al., 1989) and analgesic (Shaaban et al., 1977) activities. In order to obtain detailed information on molecular conformation, the X-ray structure determination of the title compound, (I), has been carried out and the results are presented here. \scheme
The total puckering amplitude (Cremer & Pople, 1975) of the tetrahydropyridine ring, B, is QT = 0.450 (2) Å and the values of the lowest displacement asymmetry parameters (Nardelli, 1983a), Δ2(C6—C1) = 0.053 (1) and ΔS(C12) = 0.060 (1), are indicative of a conformation intermediate between half-chair and sofa. The total puckering amplitude of the cyclopentene ring, A, is QT = 0.276 (3) Å and the value ΔS(C11) = 0.004 (2) of the lowest asymmetry parameter is indicative of an envelope conformation. The cyclopentene ring makes a dihedral angle of 73.3 (1)° with the mean plane passing through the tetrahydroquinoline. The C7—C11—C12—C13 torsion angle of 175.1 (2)° is indicative of the way the indole substituent is bonded to the tetrahydroquinoline. The best plane through the tetrahydroquinoline makes a dihedral angle of 45.45 (4)° with the mean plane passing through the indole.
The indole system is not strictly planar, the dihedral angle formed by the benzo and pyrrole planes being 2.6 (1)°. Atom N15 deviates by 0.148 (2) Å from the mean plane passing through C14, C16 and S22. This slight pyramidalization behaviour is also observed in related indoles (Yokum & Fronczek, 1997; Beddoes et al., 1986). The torsion angles O23—S22—N15—C16 = 171.2 (2) and O23—S22—C25—C26 = 43.2 (2)° describe the conformation of the phenylsulfonyl group with respect to the indole system, which causes the best planes of the indole and phenyl rings to form a dihedral angle of 85.6 (1)°, as observed in similar structures (Yokum & Fronczek, 1997).
In the indole system, the endocyclic angles at C17 and C20 are contracted to 116.7 (2) and 118.5 (2)°, respectively, while those at C16 and C19 are expanded to 122.6 (2) and 121.2 (2)°, respectively. This would appear to be a real effect caused by the fusion of the smaller pyrrole ring to the six-membered benzene ring and the strain is taken up by angular distortion rather than by bond length distortions. A similar effect has also been observed by Govindasamy et al. (1999) and Sivaraman et al. (1996, 1994). The bond distances S22═O24 = 1.432 (2), S22═O23 = 1.429 (2) and S22—C25 = 1.758 (2) Å are comparable with the reported values [S═O = 1.435 (5) and S—C = 1.767 (7) Å; Govindasamy et al., 1998], whereas S22—N15 = 1.659 (2) Å varies appreciably from the reported value of 1.685 (5) Å.
The orientation of the phenyl ring, D, is conditioned by the weak interaction C30—H30···O24, while the orientation of the indole substituent is influenced by the weak interaction C17—H17···O24 (Table 2). The torsion angles O24—S22—C25—C30 = -1.3 (2), N15—S22—C25—C30 = 113.3 (2), O24—S22—N15—C16 = 41.3 (2) and S22—N15—C16—C17 = -18.2 (3)° quantitatively define these orientations.
Apart from the normal van der Waals interactions, the packing of the molecule in the solid state is stabilized by C—H···O and C—H···N type intermolecular hydrogen bonds (Table 2). O23 is involved in the formation of two hydrogen bonds by acting as an acceptor for C29—H29···O23 and C2—H2···O23 hydrogen bonds.