Table 2. Experimental and Calculated Geometric Parameters for the Heterocyclic Derivatives Calculated at the M06-2X/6-311++G(d,p) and the MP2/aug-cc-pVTZ Level of Theory.
| atoms | azepane (X-ray) | M06-2X/6-311++G(d,p) | MP2/aug-ccPVTZ | oxepane (X-ray) | M06-2X/6-311++G(d,p) | MP2/aug-ccPVTZ | thiepane (X-ray) | M06-2X/6-311++G(d,p) | MP2/aug-ccPVTZ |
|---|---|---|---|---|---|---|---|---|---|
| C1–C2 | 1.527 | 1.5335 | 1.5297 | 1.546 | 1.5283 | 1.5239 | 1.5391 | 1.5341 | 1.5303 |
| C1–C4 | 1.527 | 1.5328 | 1.5289 | 1.510 | 1.5331 | 1.5285 | 1.5418 | 1.5368 | 1.5332 |
| C2–C3 | 1.528 | 1.5297 | 1.5255 | 1.511 | 1.5389 | 1.5285 | 1.5348 | 1.5288 | 1.5253 |
| C3–C5 | 1.526 | 1.5343 | 1.5294 | 1.511 | 1.5348 | 1.5312 | 1.5336 | 1.5293 | 1.5261 |
| C4–C6 | 1.528 | 1.5395 | 1.5351 | 1.434 | 1.529 | 1.5248 | 1.532 | 1.5277 | 1.5241 |
| C5–X | 1.456 | 1.459 | 1.4602 | 1.434 | 1.4159 | 1.4225 | 1.8423 | 1.8226 | 1.8157 |
| C6–X | 1.459 | 1.4587 | 1.4593 | 1.363 | 1.4102 | 1.4164 | 1.852 | 1.8291 | 1.8204 |
| N19–H20 | 1.02 | 1.0124 | 1.0122 | ||||||
| RMSD | 0.007 | 0.004 | 0.044 | 0.043 | 0.012 | 0.017 | |||
| Bond Angle (Ǻ) | |||||||||
| C2–C1–C4 | 111.167 | 112.9414 | 112.6682 | 109.158 | 113.6749 | 113.4912 | 113.695 | 113.2515 | |
| C3–C5–C–N19 | 112.168 | 114.4365 | 114.1215 | 114.519 | 115.6218 | 115.463 | 116.2287 | 115.7837 | |
| C4–C6–N19 | 109.062 | 117.1339 | 117.089 | 111.080 | 112.5323 | 112.4612 | 114.0879 | 113.5635 | |
| C–C–H | 109.556 | 109.7392 | 109.3667 | 109.510 | 109.5672 | 109.5859 | 109.5322 | 109.3938 | |
| RMSD | 4.286 | 4.199 | 2.436 | 2.323 | |||||
| Dihedral Angles | |||||||||
| C1C4C6N19 | –41.612 | –39.3082 | –39.8087 | –73.612 | 52.1585 | –72.2138 | –72.3498 | –72.2894 | |
| C2–C1–C4–H16 | –74.232 | –153.0755 | –152.5683 | –177.707 | –157.5784 | –156.3957 | –142.2856 | –141.4007 | |
| C1C4C6H12 | 168.626 | –162.7305 | –163.133 | 164.936 | –163.8118 | –163.7655 | –46.7798 | –45.7234 | |