Table 2. Selected Geometric Bond Lengths, Bond Angles, and Dihedral Angles of the Optimized 9a–h Using B3LYP/6-311G**.
| compound | bond lengths (Å) | bond angles | dihedral angles | |||
|---|---|---|---|---|---|---|
| 9a | C18–O19 | 1.407 | C17–O19–C18 | 124.412 | C13–C14–C18–O20 | 0.000 |
| C18–O20 | 1.192 | O19–C18–O20 | 116.604 | N11–C13–C14–C15 | 0.000 | |
| C18–C14 | 1.484 | O19–C18–C14 | 115.255 | N11–C13–C14–C18 | 0.000 | |
| C13–C14 | 1.465 | C13–C14–C18 | 119.026 | S12–C13–C14–C18 | 180.000 | |
| C4–S12 | 1.748 | S12–C13–C14 | 119.697 | S12–C13–C14–C15 | 0.000 | |
| C13–N11 | 1.290 | N11–C13–C14 | 125.967 | C4–S12–C13–C14 | 180.000 | |
| C3–C4 | 1.414 | N11–C13–S12 | 38.982 | C6–C4–S12–C13 | 180.000 | |
| C2–C3 | 1.401 | C3–N11–C13 | 112.385 | C2–C3–N11–C13 | 180.000 | |
| 9b | C18–O19 | 1.408 | C17–O19–C18 | 124.351 | C13–C14–C18–O20 | 0.000 |
| C18–O20 | 1.191 | O19–C18–O20 | 121.330 | N11–C13–C14–C15 | 180.000 | |
| C18–C14 | 1.485 | O19–C18–C14 | 115.216 | N11–C13–C14–C18 | 0.000 | |
| C13–C14 | 1.466 | C13–C14–C18 | 118.955 | S12–C13–C14–C18 | 180.000 | |
| C4–S12 | 1.748 | S12–C13–C14 | 119.763 | S12–C13–C14–C15 | 0.000 | |
| C13–N11 | 1.290 | N11–C13–C14 | 125.829 | C4–S12–C13–C14 | 180.000 | |
| C3–C4 | 1.414 | N11–C13–S12 | 114.409 | C6–C4–S12–C13 | 180.000 | |
| C2–C3 | 1.401 | C3–N11–C13 | 112.339 | C2–C3–N11–C13 | 180.000 | |
| 9c | C18–O19 | 1.409 | C17–O19–C18 | 124.366 | C13–C14–C18–O20 | 0.000 |
| C18–O20 | 1.192 | O19–C18–O20 | 116.572 | N11–C13–C14–C15 | 180.000 | |
| C18–C14 | 1.484 | O19–C18–C14 | 115.207 | N11–C13–C14–C18 | 0.000 | |
| C13–C14 | 1.466 | C13–C14–C18 | 118.991 | S12–C13–C14–C18 | 180.000 | |
| C4–S12 | 1.747 | S12–C13–C14 | 119.731 | S12–C13–C14–C15 | 0.000 | |
| C13–N11 | 1.290 | N11–C13–C14 | 125.852 | C4–S12–C13–C14 | 180.000 | |
| C3–C4 | 1.414 | N11–C13–S12 | 114.417 | C6–C4–S12–C13 | 180.000 | |
| C2–C3 | 1.4015 | C3–N11–C13 | 112.335 | C2–C3–N11–C13 | 180.000 | |
| 9d | C18–O19 | 1.405 | C17–O19–C18 | 124.329 | C13–C14–C18–O20 | 0.000 |
| C18–O20 | 1.193 | O19–C18–O20 | 116.664 | N11–C13–C14–C15 | 180.000 | |
| C18–C14 | 1.484 | O19–C18–C14 | 115.265 | N11–C13–C14–C18 | 0.000 | |
| C13–C14 | 1.465 | C13–C14–C18 | 119.030 | S12–C13–C14–C18 | 180.000 | |
| C4–S12 | 1.748 | S12–C13–C14 | 119.691 | S12–C13–C14–C15 | 0.000 | |
| C13–N11 | 1.290 | N11–C13–C14 | 125.993 | C4–S12–C13–C14 | 180.000 | |
| C3–C4 | 1.414 | N11–C13–S12 | 114.316 | C6–C4–S12–C13 | 180.000 | |
| C2–C3 | 1.401 | C3–N11–C13 | 112.403 | C2–C3–N11–C13 | 180.000 | |
| 9e | C18–O19 | 1.417 | C17–O19–C18 | 124.476 | C13–C14–C18–O20 | 0.000 |
| C18–O20 | 1.189 | O19–C18–O20 | 116.236 | N11–C13–C14–C15 | 180 | |
| C18–C14 | 1.484 | O19–C18–C14 | 115.154 | N11–C13–C14–C18 | 0.000 | |
| C13–C14 | 1.4659 | C13–C14–C18 | 118.882 | S12–C13–C14–C18 | 180 | |
| C4–S12 | 1.747 | S12–C13–C14 | 119.863 | S12–C13–C14–C15 | 0.000 | |
| C13–N11 | 1.291 | N11–C13–C14 | 125.602 | C4–S12–C13–C14 | 180.000 | |
| C3–C4 | 1.415 | N11–C13–S12 | 114.535 | C6–C4–S12–C13 | 180.000 | |
| C2–C3 | 1.402 | C3–N11–C13 | 112.257 | C2–C3–N11–C13 | 180.000 | |
| 9f | C18–O19 | 1.412 | C17–O19–C18 | 124.330 | C13–C14–C18–O20 | 2.813 |
| C18–O20 | 1.195 | O19–C18–O20 | 116.547 | N11–C13–C14–C15 | ––148.804 | |
| C18–C14 | 1.473 | O19–C18–C14 | 115.271 | N11–C13–C14–C18 | 31.707 | |
| C13–C14 | 1.464 | C13–C14–C18 | 118.576 | S12–C13–C14–C18 | –148.749 | |
| C4–S12 | 1.749 | S12–C13–C14 | 119.403 | S12–C13–C14–C15 | 30.740 | |
| C13–N11 | 1.290 | N11–C13–C14 | 125.862 | C4–S12–C13–C14 | ––178.502 | |
| C3–C4 | 1.415 | N11–C13–S12 | 114.734 | C6–C4–S12–C13 | –179.552 | |
| C2–C3 | 1.401 | C3–N11–C13 | 112.047 | C2–C3–N11–C13 | 157.680 | |
| 9g | C18–O19 | 1.414 | C17–O19–C18 | 124.404 | C13–C14–C18–O20 | 0.000 |
| C18–O20 | 1.189 | O19–C18–O20 | 116.426 | N11–C13–C14–C15 | 180.000 | |
| C18–C14 | 1.483 | O19–C18–C14 | 115.021 | N11–C13–C14–C18 | 0.000 | |
| C13–C14 | 1.466 | C13–C14–C18 | 118.934 | S12–C13–C14–C18 | 180.000 | |
| C4–S12 | 1.747 | S12–C13–C14 | 119.856 | S12–C13–C14–C15 | 0.000 | |
| C13–N11 | 1.290 | N11–C13–C14 | 125.670 | C4–S12–C13–C14 | 180.000 | |
| C3–C4 | 1.415 | N11–C13–S12 | 114.475 | C6–C4–S12–C13 | 180.000 | |
| C2––C3 | 1.402 | C3–N11–C13 | 112.307 | C2–C3–N11–C13 | 180.000 | |
| 9h | C18–O19 | 1.412 | C17––O19–C18 | 124.530 | C13–C14–C18–O20 | 0.000 |
| C18–O20 | 1.190 | O19–C18–O20 | 116.481 | N11–C13–C14–C15 | 180.000 | |
| C18–C14 | 1.484 | O19–C18–C14 | 115.078 | N11–C13–C14–C18 | 0.000 | |
| C13–C14 | 1.465 | C13–C14–C18 | 118.966 | S12–C13–C14–C18 | 180.000 | |
| C4–S12 | 1.748 | S12–C13–C14 | 119.820 | S12–C13–C14–C15 | 0.000 | |
| C13–N11 | 1.290 | N11–C13–C14 | 125.716 | C4–S12–C13–C14 | 180.000 | |
| C3–C4 | 1.414 | N11–C13–S12 | 114.463 | C6–C4–S12–C13 | 180.000 | |
| C2–C3 | 1.402 | C3–N11–C13 | 112.308 | C2–C3–N11–C13 | 180.000 | |