Table 1. Hydrogen bonds and short inter-ion contacts (Å, °).
Cg1, Cg2 and Cg3 represent the centroids of the rings (C31–C36), (C21–C26) and (C41–C46), respectively.
| Compound | D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|---|
| (I) | N1—H11⋯O31 | 1.02 (2) | 1.60 (2) | 2.616 (3) | 176 (2) |
| N1—H12⋯O32i | 0.92 (3) | 1.88 (3) | 2.792 (3) | 173 (2) | |
| C3—H3A⋯Cg1i | 0.97 | 2.96 | 3.881 (3) | 160 | |
| (II) | N1—H11⋯O31 | 0.89 (4) | 1.75 (4) | 2.620 (4) | 168 (3) |
| N1—H12⋯O32i | 0.88 (4) | 1.91 (4) | 2.786 (4) | 175 (4) | |
| (III) | N1—H11⋯O31 | 0.88 (2) | 1.83 (2) | 2.684 (3) | 163 (2) |
| N1—H11⋯O32 | 0.88 (2) | 2.60 (2) | 3.060 (3) | 113.6 (17) | |
| N1—H12⋯O32i | 0.91 (3) | 1.84 (3) | 2.746 (3) | 176 (3) | |
| C33—H33⋯O32ii | 0.93 | 2.57 | 3.327 (3) | 139 | |
| C2—H2B⋯Cg2iii | 0.97 | 2.77 | 3.482 (2) | 131 | |
| (IV) | N1—H11⋯O31 | 0.99 (3) | 1.72 (3) | 2.694 (4) | 167 (3) |
| N1—H11⋯O32 | 0.99 (3) | 2.51 (3) | 3.131 (4) | 120.9 (19) | |
| N1—H12⋯O32iii | 0.88 (3) | 1.83 (3) | 2.679 (4) | 161 (3) | |
| N1—H11⋯O41 | 0.99 (3) | 1.77 (5) | 2.67 (4) | 151 (3) | |
| N1—H11⋯O42 | 0.99 (3) | 2.52 (5) | 3.20 (4) | 126 (2) | |
| N1—H12⋯O42iii | 0.88 (3) | 1.83 (5) | 2.63 (4) | 151 (3) | |
| C34—H34⋯Cg2iv | 0.93 | 2.74 | 3.543 (5) | 145 | |
| C44—H44⋯Cg2iv | 0.93 | 2.99 | 3.73 (4) | 137 | |
| C26—H26⋯Cg3v | 0.93 | 2.96 | 3.754 (17) | 144 | |
| (V) | N1—H11⋯O31 | 0.97 (4) | 1.74 (3) | 2.682 (4) | 162 (3) |
| N1—H12⋯O32i | 0.92 (4) | 1.79 (4) | 2.700 (5) | 170 (4) | |
| C5—H5B⋯Cg1ii | 0.97 | 2.87 | 3.554 (4) | 128 | |
| C34—H34⋯Cg2vi | 0.93 | 2.93 | 3.658 (7) | 136 | |
| (VI) | N1—H11⋯O31 | 0.75 (4) | 1.98 (4) | 2.726 (4) | 170 (4) |
| N1—H12⋯O32vii | 0.88 (3) | 1.86 (3) | 2.712 (4) | 163(3 | |
| C25—H25⋯O32viii | 0.93 | 2.56 | 3.488 (4) | 173 | |
| C26—H26⋯Cg1viii | 0.93 | 2.93 | 3.697 (4) | 141 | |
| (VII) | N1—H11⋯O31 | 0.89 | 1.80 | 2.66 (3) | 162 |
| N1—H11⋯O33 | 0.89 | 1.93 | 2.80 (3) | 165 | |
| N1—H12⋯O31ix | 0.89 | 1.97 | 2.83 (3) | 162 | |
| N1—H12⋯O33ix | 0.89 | 1.74 | 2.60 (3) | 161 | |
| C25—H25⋯O34x | 0.93 | 2.50 | 3.43 (3) | 174 | |
| C26—H26⋯Cg1x | 0.93 | 2.93 | 3.716 (5) | 143 | |
| (VIII) | N1—H11⋯O31 | 1.010 (15) | 1.673 (15) | 2.6696 (19) | 168.6 (13) |
| N1—H12⋯O32i | 0.963 (16) | 1.745 (16) | 2.7077 (17) | 178.2 (10) | |
| (IX) | N1—H11⋯O31 | 1.068 (15) | 1.547 (15) | 2.6048 (15) | 169.7 (14) |
| N1—H12⋯O32i | 0.942 (15) | 1.861 (15) | 2.7797 (15) | 164.4 (14) | |
| N34—H34⋯O32xi | 0.914 (16) | 2.155 (16) | 3.0535 (18) | 167.5 (14) | |
| (X) | N1—H11⋯O31 | 0.974 (16) | 1.677 (16) | 2.6500 (19) | 176.8 (15) |
| N1—H11⋯O32 | 0.974 (16) | 2.581 (17) | 3.2169 (17) | 123.0 (12) | |
| N1—H12⋯O32i | 0.948 (17) | 1.837 (17) | 2.7709 (18) | 168.2 (16) | |
| (XI) | N1—H11⋯O31 | 0.929 (16) | 1.771 (16) | 2.6837 (16) | 166.8 (15) |
| N1—H12⋯O41 | 0.911 (16) | 1.939 (16) | 2.8324 (19) | 165.5 (14) | |
| O41—H41⋯O32xii | 0.84 (2) | 1.99 (2) | 2.8156 (19) | 168 (2) | |
| O41—H42⋯O51 | 0.90 (2) | 1.91 (2) | 2.810 (2) | 172 (2) | |
| O51—H51⋯O31i | 0.90 (2) | 1.91 (2) | 2.810 (2) | 172 (2) | |
| O51—H52⋯O22xii | 0.77 (2) | 2.25 (2) | 2.9544 (19) | 153 (2) | |
| C25—H25⋯O36i | 0.93 | 2.58 | 3.433 (2) | 153 | |
| (XII) | N1—H11⋯O33 | 0.868 (18) | 2.224 (18) | 2.9120 (19) | 136.1 (16) |
| N1—H12⋯O31i | 0.900 (18) | 1.833 (18) | 2.7142 (18) | 165.9 (16) | |
| N1—H12⋯O32i | 0.900 (19) | 2.593 (17) | 3.154 (2) | 121.2 (13) | |
| C6—H6A⋯O34xiii | 0.97 | 2.56 | 3.423 (2) | 148 | |
| (XIII) | O33—H33⋯O32 | 1.07 (2) | 1.37 (2) | 2.4447 (16) | 177.7 (16) |
| O43—H43⋯O42 | 1.00 (2) | 1.48 (2) | 2.4707 (17) | 174.0 (17) | |
| N11—H111⋯O32 | 0.927 (17) | 1.891 (17) | 2.8122 (18) | 172.3 (16) | |
| N11—H112⋯O41xiv | 0.930 (17) | 1.848 (17) | 2.7725 (17) | 172.9 (13) | |
| N21—H211⋯O42 | 0.975 (15) | 1.821 (15) | 2.7926 (16) | 174.5 (14) | |
| N21—H212⋯O31 | 0.895 (15) | 2.283 (15) | 2.9776 (17) | 134.4 (12) | |
| N21—H212⋯O34xv | 0.895 (15) | 2.428 (15) | 3.1170 (18) | 134.1 (12) | |
| C16—H16A⋯O34xv | 0.97 | 2.55 | 3.341 (2) | 138 | |
| C16—H16B⋯O44xv | 0.97 | 2.52 | 3.338 (2) | 141 | |
| C25—H25B⋯Cg4xvi | 0.97 | 2.92 | 3.8440 (16) | 159 | |
| (XIV) | N1—H11⋯O31 | 0.89 | 2.01 | 2.894 (5) | 171 |
| N1—H11⋯O33 | 0.89 | 1.73 | 2.584 (7) | 160 | |
| N1—H12⋯O41 | 0.89 | 1.97 | 2.8251 (15) | 161 | |
| O32—H32⋯O32xvii | 0.82 | 1.54 | 2.355 (7) | 176 | |
| O34—H34⋯O34xvii | 0.82 | 2.03 | 2.820 (9) | 161 | |
| O42—H42⋯O42xviii | 0.82 | 1.62 | 2.4352 (12) | 177 | |
| (XV) | N1—H11⋯O31 | 0.79 (4) | 2.40 (4) | 3.028 (4) | 137 (3) |
| N1—H11⋯O36xii | 0.79 (4) | 2.43 (4) | 2.977 (4) | 128 (3) | |
| N1—H11⋯O35xix | 0.79 (4) | 2.50 (3) | 2.942 (3) | 117 (3) | |
| N1—H12⋯O41 | 0.89 (4) | 1.91 (4) | 2.792 (5) | 168 (3) | |
| O33—H33⋯O34xx | 0.77 (4) | 2.14 (4) | 2.800 (3) | 144 (4) | |
| O34—H34⋯O31xx | 0.82 (4) | 2.11 (4) | 2.836 (3) | 148 (3) | |
| O36—H36⋯O32ii | 0.81 (4) | 1.68 (4) | 2.478 (3) | 167(3 | |
| O41—H41⋯O33xxi | 0.82 (5) | 1.94 (5) | 2.753 (4) | 167 (3) | |
| O41—H42⋯O31xii | 0.87 (5) | 1.90 (5) | 2.766 (4) | 169 (3) | |
| O51—H51⋯O41 | 0.98 (4) | 1.80 (5) | 2.776 (5) | 172 (9) | |
| O51—H52⋯O22xii | 0.97 (7) | 2.22 (7) | 3.054 (7) | 144 (6) | |
| O51—H52⋯N4xii | 0.97 (7) | 2.48 (6) | 3.307 (6) | 143 (5) | |
| C23—H23⋯Cg2xxii | 0.93 | 2.91 | 3.722 (4) | 147 |
Symmetry codes: (i) 1 − x, 1 − y, 1 − z; (ii) 1 + x, y, z; (iii) x, 1 − y, −
+ z; (iv) − + x, 
− y, − + z; (v) + x, − + y, z; (vi) −1 + x, y, 1 + z; (vii) + x, − y, 1 − z; (Viii) − x, 1 − y, − + z; (ix) − + x, − y, 1 − z; (x) − x, 1 − y, + z; (xi) x, − y, − + z; (xii) −1 + x, y, z; (xiii) x, 1 + y, z; (xiv) x, −1 + y, z; (xv) −x, 1 − y, 1 − z; (xvi) 1 − x, −y, −z; (xvii) 1 − x, 1 − y, 2 − z; (xviii) 1 − x, −y, 2 − z; (xix) 2 − x, + y, 1 − z; (xx) 2 − x, − + y, 1 − z; (xxi) −1 + x, 1 + y, z; (xxii) 1 − x, + y, −z.