Table 3. Halogen- and chalcogen-bond geometries (Å, °).
| Compound | d(D⋯A) | R XB i | θ(C—D⋯A) | θ(D⋯A—C) | θ1 – θ2 ii | ψiii | |
|---|---|---|---|---|---|---|---|
| 2(IT)·(1,3-F4DIB) | I1⋯S1 | 3.2265 (6) | 0.85 | 174.51 (4) | 113.51 (5) | 61.00 | 0.79 |
| I2⋯S1 | 3.2860 (5) | 0.87 | 176.10 (4) | 99.67 (5) | 76.43 | 0.03 | |
| (IT)·(1,3,5-F3I3B) | I1⋯I3 | 3.8376 (6) | 0.97 | 162.95 (8) | 106.24 (7) | 56.71 | 0.64 |
| I2⋯S1 | 3.1505 (8) | 0.83 | 171.86 (7) | 101.89 (10) | 69.97 | 0.48 | |
| I3⋯S1 | 3.1754 (8) | 0.84 | 177.68 (8) | 90.59 (9) | 87.09 | 0.18 | |
| 4(MBZIM)·3(1,3-F4DIB) | I1⋯S3 | 3.3361 (10) | 0.88 | 172.18 (8) | 136.86 (8) | 35.32 | 0.83 |
| I6⋯S2 | 3.2150 (9) | 0.85 | 166.06 (8) | 134.24 (8) | 31.82 | 0.74 | |
| (MBZIM)·(1,4-F4DIB) | I1⋯S1 | 3.2573 (9) | 0.86 | 168.29 (6) | 131.28 (8) | 37.01 | 0.57 |
| (MBZIM)·(TIE) | I1⋯S1 | 3.5368 (14) | 0.94 | 173.83 (17) | 71.37 (16) | 102.46 | 0.66 |
| I3⋯S1 | 3.2702 (14) | 0.87 | 177.05 (17) | 118.15 (17) | 58.90 | 0.64 | |
| (MMBZIM)·(1,2-F4DIB) | I1⋯S1 | 3.6404 (10) | 0.96 | 154.63 (12) | 95.76 (13) | 58.87 | 0.47 |
| I2⋯S1 | 3.2307 (11) | 0.85 | 169.63 (11) | 106.66 (15) | 62.97 | 0.04 | |
| 2(MMBZIM)·(1,4-F4DIB)·2(H2O) | I1⋯S1 | 3.2516 (4) | 0.86 | 169.16 (4) | 96.12 (4) | 73.04 | 0.37 |
| (MMBZIM)·(1,3,5-F3I3B) | I2⋯S1 | 3.474 (2) | 0.92 | 164.1 (3) | 92.1 (3) | 72.0 | 0.71 |
| I3⋯S1 | 3.463 (2) | 0.92 | 176.7 (3) | 96.5 (3) | 80.2 | 0.50 | |
| (MBZOX)·(1,2-F4DIB) | I2⋯S1 | 3.2853 (19) | 0.87 | 166.65 (19) | 105.4 (3) | 61.3 | 0.19 |
| (MBZOX)·(1,3-F4DIB) | I1⋯S1 | 3.4132 (7) | 0.90 | 174.53 (6) | 105.63 (8) | 68.90 | 0.19 |
| I2⋯S1 | 3.6787 (6) | 0.97 | 159.40 (6) | 92.48 (7) | 66.92 | 0.66 | |
| S1⋯I1 | 3.7536 (7) | 0.99 | 160.34 (7) | 105.80 (6) | 54.54 | 0.53 | |
| 2(MBZOX)·(1,4-F4DIB) | I1⋯S1 | 3.2287 (11) | 0.85 | 174.60 (9) | 109.39 (13) | 65.21 | 0.74 |
| (MBZOX)·(1,3,5-F3I3B) | I1⋯S1 | 3.4114 (14) | 0.90 | 171.55 (13) | 100.14 (19) | 71.41 | 0.14 |
| I2⋯I3 | 3.9110 (7) | 0.99 | 147.22 (13) | 79.55 (13) | 67.67 | 0.62 | |
| I3⋯S1 | 3.6774 (13) | 0.97 | 157.67 (15) | 95.79 (16) | 61.88 | 0.67 | |
| S1⋯I1 | 3.7385 (14) | 0.99 | 163.12 (17) | 98.99 (14) | 64.13 | 0.44 | |
| 3(MBZTH)·4(1,2-F4DIB) | I1⋯S5 | 3.380 (4) | 0.89 | 177.9 (4) | 113.3 (5) | 64.6 | 0.81 |
| I2⋯S5 | 3.353 (4) | 0.89 | 163.7 (4) | 128.9 (5) | 34.8 | 0.61 | |
| I3⋯S3 | 3.371 (5) | 0.89 | 169.0 (4) | 96.4 (7) | 72.6 | 0.02 | |
| I4⋯S3 | 3.754 (4) | 0.99 | 173.7 (4) | 100.5 (6) | 73.2 | 0.76 | |
| I5⋯S1 | 3.380 (4) | 0.89 | 177.9 (4) | 113.3 (5) | 64.6 | 0.81 | |
| I6⋯I7 | 3.8766 (14) | 0.95 | 170.5 (4) | 118.1 (4) | 52.4 | 0.73 | |
| I6⋯S1 | 3.391 (5) | 0.90 | 168.1 (4) | 111.3 (6) | 56.8 | 0.76 | |
| (MBZTH)·(1,3-F4DIB) | I1⋯S1 | 3.3724 (5) | 0.89 | 168.06 (6) | 120.18 (6) | 47.88 | 0.64 |
| I2⋯S1 | 3.4140 (5) | 0.90 | 157.68 (4) | 106.00 (5) | 51.68 | 0.66 | |
| (MBZTH)·2(1,3-F4DIB) | I1⋯S3 | 3.3426 (17) | 0.88 | 168.34 (18) | 103.3 (2) | 65.0 | 0.25 |
| I2⋯S2 | 3.7429 (17) | 0.99 | 152.94 (18) | 121.7 (4)iii | 31.2 | 0.23 | |
| I3⋯S1 | 3.3548 (18) | 0.89 | 166.60 (17) | 100.3 (2) | 66.3 | 0.64 | |
| I4⋯S4 | 3.6744 (17) | 0.97 | 148.74 (18) | 118.4 (4)iii | 30.4 | 0.65 | |
| I5⋯I4 | 3.7971 (10) | 0.96 | 163.30 (19) | 82.92 (18) | 80.38 | 0.52 | |
| I8⋯I2 | 3.7950 (9) | 0.96 | 170.03 (18) | 84.69 (18) | 85.34 | 0.71 | |
| 2(MBZTH)·(1,4-F4DIB) | I1⋯S1 | 3.3013 (7) | 0.87 | 178.16 (7) | 103.84 (10) | 74.32 | 0.60 |
| (MBZTH)·(1,3,5-F3I3B) | I1⋯S1 | 3.4551 (10) | 0.91 | 169.01 (9) | 97.89 (13) | 71.12 | 0.71 |
| S2⋯I3 | 3.7777 (10) | 1.00 | 158.73 (12) | 117.64 (10) | 41.09 | 0.52 | |
| (MBZTH)·(TIE) | I1⋯I3 | 3.9459 (7) | 1.00 | 171.07 (14) | 70.7 (3) | 100.4 | 0.55 |
| I3⋯S1 | 3.2826 (13) | 0.87 | 162.1 (3) | 122.51 (19) | 39.6 | 0.41 | |
| I4⋯S1 | 3.6514 (19) | 0.97 | 161.9 (3) | 77.0 (2) | 84.9 | 0.46 |
Notes: (i) R XB = d(X⋯Y)/Σd(vdW), the ratio of the distance between the donor atom (i.e. I) and the acceptor atom (i.e. S) to the sum of their van der Waals (vdW) radii (S = 1.80 Å and I = 1.98 Å) (Auffinger et al., 2004 ▸). (ii) θ1 – θ2 = |{[θ(C—D⋯A)] – [θ(D⋯A—C)]}|. (iii) Linearity parameter (Setter et al., 2020 ▸).