organic compounds
In the title compound, C11H13NOS, the thiophene ring is planar while the central six-membered ring has a half-chair conformation and the second ring of the quinolizine moiety is in a chair conformation. The angles at the N atom sum to 331.22°, indicating pyramidalization of this atom.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003454/kp6040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003454/kp6040Isup2.hkl |
CCDC reference: 269802
Computing details top
Data collection: KM-4 Software (Kuma, 1992); cell refinement: KM-4 Software; data reduction: KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
5,6,7,8-tetrahydro-4aH-thieno[3,2-b]quinolizin-4(10H)-one top
Crystal data top
C11H13NOS | F(000) = 440 |
Mr = 207.28 | Dx = 1.357 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2238 reflections |
a = 6.808 (2) Å | θ = 2.3–34.1° |
b = 18.770 (9) Å | µ = 0.28 mm−1 |
c = 8.256 (3) Å | T = 298 K |
β = 105.84 (3)° | Prism, colorless |
V = 1014.9 (7) Å3 | 0.60 × 0.50 × 0.30 mm |
Z = 4 |
Data collection top
Kuma KM-4 CCD diffractometer | 1765 reflections with F2 > 2σ(F2) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 27.1°, θmin = 2.2° |
ω scans | h = −8→8 |
8775 measured reflections | k = −24→0 |
2238 independent reflections | l = −10→5 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0629P)2 + 0.1855P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
2238 reflections | Δρmax = 0.40 e Å−3 |
128 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0060 (19) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C2 | 0.2977 (3) | 0.03415 (9) | 0.1691 (2) | 0.0562 (4) | |
H2 | 0.3072 | −0.0149 | 0.1858 | 0.067* | |
C3 | 0.1215 (3) | 0.07026 (8) | 0.1324 (2) | 0.0462 (4) | |
H3 | −0.0055 | 0.0494 | 0.1211 | 0.055* | |
C4 | −0.0034 (2) | 0.19918 (8) | 0.05778 (18) | 0.0373 (3) | |
C5 | −0.0812 (2) | 0.32880 (8) | 0.0739 (2) | 0.0441 (4) | |
H5A | −0.2122 | 0.3218 | −0.0080 | 0.053* | |
H5B | −0.0994 | 0.3212 | 0.1851 | 0.053* | |
C6 | −0.0091 (3) | 0.40474 (9) | 0.0610 (2) | 0.0512 (4) | |
H6A | −0.0072 | 0.4146 | −0.0539 | 0.061* | |
H6B | −0.1027 | 0.4379 | 0.0909 | 0.061* | |
C7 | 0.2027 (3) | 0.41451 (8) | 0.1781 (2) | 0.0537 (4) | |
H7A | 0.1971 | 0.4104 | 0.2939 | 0.064* | |
H7B | 0.2525 | 0.4618 | 0.1628 | 0.064* | |
C8 | 0.3481 (3) | 0.35896 (8) | 0.1435 (2) | 0.0475 (4) | |
H8A | 0.3627 | 0.3659 | 0.0309 | 0.057* | |
H8B | 0.4815 | 0.3650 | 0.2227 | 0.057* | |
C9 | 0.4245 (2) | 0.23644 (8) | 0.1264 (2) | 0.0398 (3) | |
H9A | 0.5553 | 0.2436 | 0.2084 | 0.048* | |
H9B | 0.4419 | 0.2448 | 0.0151 | 0.048* | |
C10 | 0.1524 (2) | 0.14472 (7) | 0.11284 (17) | 0.0360 (3) | |
C11 | 0.0714 (2) | 0.27471 (7) | 0.04268 (16) | 0.0339 (3) | |
H11 | 0.0813 | 0.2813 | −0.0726 | 0.041* | |
C13 | 0.3526 (2) | 0.16222 (8) | 0.13807 (17) | 0.0370 (3) | |
S1 | 0.50491 (7) | 0.08858 (2) | 0.18172 (7) | 0.05591 (18) | |
O14 | −0.18523 (17) | 0.18518 (7) | 0.0166 (2) | 0.0637 (4) | |
N12 | 0.27451 (17) | 0.28635 (6) | 0.15825 (14) | 0.0346 (3) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0660 (11) | 0.0333 (8) | 0.0708 (12) | 0.0014 (7) | 0.0210 (9) | 0.0036 (7) |
C3 | 0.0536 (9) | 0.0372 (7) | 0.0512 (9) | −0.0082 (6) | 0.0201 (7) | −0.0042 (6) |
C4 | 0.0343 (7) | 0.0402 (7) | 0.0393 (7) | −0.0027 (6) | 0.0134 (6) | −0.0047 (6) |
C5 | 0.0414 (8) | 0.0435 (8) | 0.0486 (8) | 0.0084 (6) | 0.0144 (6) | 0.0038 (6) |
C6 | 0.0604 (10) | 0.0385 (8) | 0.0556 (10) | 0.0109 (7) | 0.0172 (8) | 0.0067 (7) |
C7 | 0.0681 (11) | 0.0340 (8) | 0.0561 (10) | 0.0007 (7) | 0.0118 (8) | −0.0035 (7) |
C8 | 0.0469 (8) | 0.0355 (8) | 0.0579 (10) | −0.0073 (6) | 0.0105 (7) | 0.0010 (7) |
C9 | 0.0317 (6) | 0.0381 (7) | 0.0507 (8) | −0.0014 (6) | 0.0127 (6) | 0.0000 (6) |
C10 | 0.0405 (7) | 0.0333 (7) | 0.0361 (7) | −0.0030 (6) | 0.0134 (6) | −0.0042 (5) |
C11 | 0.0342 (7) | 0.0375 (7) | 0.0305 (6) | 0.0009 (5) | 0.0097 (5) | 0.0007 (5) |
C13 | 0.0366 (7) | 0.0350 (7) | 0.0393 (7) | 0.0026 (5) | 0.0105 (6) | −0.0010 (5) |
S1 | 0.0456 (3) | 0.0408 (3) | 0.0784 (4) | 0.00987 (16) | 0.0120 (2) | 0.00354 (19) |
O14 | 0.0330 (6) | 0.0544 (7) | 0.1013 (11) | −0.0064 (5) | 0.0145 (6) | −0.0049 (7) |
N12 | 0.0341 (6) | 0.0310 (6) | 0.0375 (6) | −0.0019 (4) | 0.0077 (5) | −0.0011 (4) |
Geometric parameters (Å, º) top
C2—C3 | 1.339 (2) | C7—C8 | 1.518 (2) |
C2—S1 | 1.7214 (19) | C7—H7A | 0.9700 |
C2—H2 | 0.9300 | C7—H7B | 0.9700 |
C3—C10 | 1.429 (2) | C8—N12 | 1.4687 (19) |
C3—H3 | 0.9300 | C8—H8A | 0.9700 |
C4—O14 | 1.2196 (18) | C8—H8B | 0.9700 |
C4—C10 | 1.454 (2) | C9—N12 | 1.4617 (18) |
C4—C11 | 1.523 (2) | C9—C13 | 1.489 (2) |
C5—C6 | 1.521 (2) | C9—H9A | 0.9700 |
C5—C11 | 1.524 (2) | C9—H9B | 0.9700 |
C5—H5A | 0.9700 | C10—C13 | 1.362 (2) |
C5—H5B | 0.9700 | C11—N12 | 1.4660 (18) |
C6—C7 | 1.512 (3) | C11—H11 | 0.9800 |
C6—H6A | 0.9700 | C13—S1 | 1.7062 (16) |
C6—H6B | 0.9700 | ||
C3—C2—S1 | 112.47 (13) | N12—C8—H8A | 109.3 |
C3—C2—H2 | 123.8 | C7—C8—H8A | 109.3 |
S1—C2—H2 | 123.8 | N12—C8—H8B | 109.3 |
C2—C3—C10 | 111.71 (15) | C7—C8—H8B | 109.3 |
C2—C3—H3 | 124.1 | H8A—C8—H8B | 108.0 |
C10—C3—H3 | 124.1 | N12—C9—C13 | 109.25 (11) |
O14—C4—C10 | 122.28 (14) | N12—C9—H9A | 109.8 |
O14—C4—C11 | 120.97 (14) | C13—C9—H9A | 109.8 |
C10—C4—C11 | 116.63 (12) | N12—C9—H9B | 109.8 |
C6—C5—C11 | 111.40 (13) | C13—C9—H9B | 109.8 |
C6—C5—H5A | 109.3 | H9A—C9—H9B | 108.3 |
C11—C5—H5A | 109.3 | C13—C10—C3 | 113.01 (13) |
C6—C5—H5B | 109.3 | C13—C10—C4 | 119.51 (13) |
C11—C5—H5B | 109.3 | C3—C10—C4 | 127.28 (13) |
H5A—C5—H5B | 108.0 | N12—C11—C4 | 111.26 (11) |
C7—C6—C5 | 109.77 (13) | N12—C11—C5 | 110.86 (12) |
C7—C6—H6A | 109.7 | C4—C11—C5 | 110.33 (11) |
C5—C6—H6A | 109.7 | N12—C11—H11 | 108.1 |
C7—C6—H6B | 109.7 | C4—C11—H11 | 108.1 |
C5—C6—H6B | 109.7 | C5—C11—H11 | 108.1 |
H6A—C6—H6B | 108.2 | C10—C13—C9 | 123.30 (13) |
C6—C7—C8 | 110.69 (14) | C10—C13—S1 | 111.23 (11) |
C6—C7—H7A | 109.5 | C9—C13—S1 | 125.47 (11) |
C8—C7—H7A | 109.5 | C13—S1—C2 | 91.57 (8) |
C6—C7—H7B | 109.5 | C9—N12—C11 | 111.62 (11) |
C8—C7—H7B | 109.5 | C9—N12—C8 | 107.99 (12) |
H7A—C7—H7B | 108.1 | C11—N12—C8 | 111.51 (12) |
N12—C8—C7 | 111.53 (14) | ||
S1—C2—C3—C10 | 0.24 (19) | C4—C10—C13—C9 | 5.4 (2) |
C11—C5—C6—C7 | −54.44 (19) | C3—C10—C13—S1 | 1.17 (16) |
C5—C6—C7—C8 | 54.5 (2) | C4—C10—C13—S1 | −173.98 (10) |
C6—C7—C8—N12 | −56.8 (2) | N12—C9—C13—C10 | 24.4 (2) |
C2—C3—C10—C13 | −0.9 (2) | N12—C9—C13—S1 | −156.27 (11) |
C2—C3—C10—C4 | 173.78 (15) | C10—C13—S1—C2 | −0.88 (12) |
O14—C4—C10—C13 | 172.27 (15) | C9—C13—S1—C2 | 179.76 (14) |
C11—C4—C10—C13 | −3.84 (19) | C3—C2—S1—C13 | 0.36 (15) |
O14—C4—C10—C3 | −2.1 (2) | C13—C9—N12—C11 | −56.30 (16) |
C11—C4—C10—C3 | −178.23 (13) | C13—C9—N12—C8 | −179.20 (12) |
O14—C4—C11—N12 | 156.36 (14) | C4—C11—N12—C9 | 58.75 (14) |
C10—C4—C11—N12 | −27.47 (16) | C5—C11—N12—C9 | −178.07 (11) |
O14—C4—C11—C5 | 32.89 (19) | C4—C11—N12—C8 | 179.63 (11) |
C10—C4—C11—C5 | −150.94 (13) | C5—C11—N12—C8 | −57.20 (16) |
C6—C5—C11—N12 | 55.82 (17) | C7—C8—N12—C9 | −178.92 (14) |
C6—C5—C11—C4 | 179.53 (13) | C7—C8—N12—C11 | 58.11 (18) |
C3—C10—C13—C9 | −179.45 (14) |