Table 2. Selected geometric parameters (Å, °) calculated with X-RAY, AM1, PM3, HF and DFT .
| Parameters | X-RAY | AM1 | PM3 | HFa | DFT/B3LYPa |
|---|---|---|---|---|---|
| C8—N1 | 1.276 (19) | 1.292 | 1.302 | 1.262 | 1.293 |
| C2—O1 | 1.355418) | 1.368 | 1.357 | 1.336 | 1.344 |
| C1—C6 | 1.396 (2) | 1.406 | 1.401 | 1.393 | 1.406 |
| C1—C8 | 1.448 (2) | 1.466 | 1.459 | 1.467 | 1.449 |
| C1—C2 | 1.397 (2) | 1.408 | 1.411 | 1.402 | 1.423 |
| N1—C9 | 1.418 (19) | 1.409 | 1.431 | 1.408 | 1.406 |
| C9—C10 | 1.384 (2) | 1.414 | 1.401 | 1.391 | 1.403 |
| C12—Cl1 | 1.734 (15) | 1.699 | 1.684 | 1.743 | 1.758 |
| C5—O2 | 1.3756 (18) | 1.385 | 1.386 | 1.355 | 1.371 |
| C11—C12—Cl1 | 120.72 (12) | 119.860 | 119.505 | 119.595 | 119.538 |
| C6—C5—O2 | 115.56 (14) | 114.847 | 113.926 | 116.374 | 116.232 |
| C6—C1—C8 | 119.18 (13) | 116.153 | 118.078 | 118.004 | 119.327 |
| C9—N1 —C8 | 121.22 (13) | 121.780 | 122.176 | 120.342 | 121.253 |
| C14—C9—N1 | 124.68 (13) | 123.445 | 122.813 | 122.881 | 123.392 |
| N1—C8—C1 | 122.35 (14) | 123.800 | 119.635 | 123.408 | 122.250 |
| N1—C9—C10 | 117.10 (13) | 117.991 | 116.829 | 118.015 | 117.770 |
| C8—C1—C2—O1 | −0.9 (2) | −0.050 | −0.030 | −0.111 | −0.085 |
| C6—C5—O2—C7 | −172.96 (15) | 179.476 | 179.983 | 179.698 | −179.874 |
| C10—C9—N1—C8 | −172.84 (13) | −149.450 | 179.999 | 62.793 | −147.450 |
| N1—C8—C1—C6 | 177.90 (14) | −177.484 | −0.066 | −179.307 | −179.448 |
| C1—C8—N1—C9 | −178.85 (13) | −179.157 | 179.991 | −178.540 | −177.303 |
Notes: (a) 6-31G(d,p).