Table 2. Comparison of selected (X-ray and DFT bond lengths and angles (Å, °) in the title compound and related structures.
| X-ray | B3LYP/6–311G(d,p) | (III)a | (IV)b | |
|---|---|---|---|---|
| O1—N2 | 1.413 (3) | 1.3949 | 1.417 | 1.4100 |
| O1—C5 | 1.339 (4) | 1.3481 | 1.356 | 1.3526 |
| N2—C3 | 1.299 (3) | 1.3115 | 1.304 | 1.3044 |
| C3—C6 | 1.488 (4) | 1.5065 | 1.501 | 1.504 |
| C5—C17 | 1.485 (4) | 1.4868 | 1.476 | 1.478 |
| C6—C7 | 1.488 (4) | 1.5026 | 1.498 | 1.494 |
| C7—N8 | 1.349 (3) | 1.3755 | 1.377 | 1.3720 |
| C7—N15 | 1.320 (3) | 1.3092 | 1.312 | 1.3079 |
| N8—C9 | 1.371 (3) | 1.3814 | 1.386 | 1.3840 |
| C11—C16 | 1.500 (4) | 1.5112 | 1.504 | – |
| C14—N15 | 1.391 (3) | 1.388 | 1.400 | 1.3880 |
| C5—O1—N2 | 108.2 (2) | 109.1398 | 108.37 | 108.57 |
| C3—N2—O1 | 105.5 (2) | 106.0707 | 105.15 | 105.28 |
| N2—C3—C4 | 111.3 (2) | 111.0906 | 112.00 | 111.51 |
| N2—C3—C6 | 118.9 (2) | 120.8172 | 120.16 | 119.88 |
| O1—C5—C17 | 117.0 (3) | 116.8621 | 116.33 | 115.90 |
| C4—C5—O1 | 109.5 (3) | 109.3513 | 109.34 | 109.15 |
| N8—C7—C6 | 121.7 (2) | 122.8089 | 123.02 | 122.62 |
| N15—C7—C6 | 125.6 (2) | 123.8733 | 123.28 | 124.10 |
| N15—C7—N8 | 112.7 (2) | 113.2373 | 113.69 | 113.28 |
| C7—N8—C9 | 107.59 (19) | 106.9514 | 106.09 | 106.49 |
| N8—C9—C14 | 105.29 (19) | 104.6015 | 105.63 | 105.05 |
| C13—C14—N15 | 130.8 (2) | 130.4265 | 129.98 | 129.63 |
| N15—C14—C9 | 109.67 (19) | 110.2891 | 110.23 | 110.42 |
| C7—N15—C14 | 104.72 (19) | 104.9141 | 104.36 | 104.75 |
Notes: (a) Results of the previous DFT-optimized geometry of 5,6-dimethyl-2-[(5-methyl-1,2-oxazol-3-yl)methyl]-1-(prop-2-en-1-yl)-1H-benzimidazole (Benyahya et al., 2017 ▸); (b) results of the previous crystallographic study of 5-methyl-3-(1-(2-pyridylmethyl)-1H-benzimidazol-2-ylmethyl)isoxazole (Doumbia et al., 2009 ▸)