Acta Cryst. (2010). E66, m1025 [ doi:10.1107/S1600536810029181 ]
In the title complex, [Ni(C27H27N7)(C3H7NO)(H2O)](C6H2N3O7)2, the NiII ion is coordinated in a slightly distorted octahedral coordination evironment by an NiN4O2 ligand set. The tris(N-methylbenzimidazol-2-ylmethyl)amine ligand is in a tetradentate mode while a coordinated water molecule and a dimethylformamide ligand complete the coordination. In the crystal structure, intermolecular O-H
O hydrogen bonds link the cation and one of the pictrate anions into four-component centrosymmetric clusters.
To a stirred solution of tris(N-methylbenzimidazol-2-ylmethyl)amine (0.0899 g, 0.2 mmol) in hot MeOH (10 ml) was added Ni(C6H2N3O7)2 (0.0103 g, 0.2 mmol) in MeOH (5 ml). A pale green crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF to form a pale green solution that was allowed to evaporate at room temperature. Green crystals suitable for X-ray diffraction studies were obtained after three weeks (Yield, 62%). Elemental analysis found: C, 47.79%; H, 3.82%; N, 18.58%; calcd. for C42 H40 N14 O16 Ni: C, 47.82%; H, 3.79%; N, 18.51%.
H atoms bonded to C atoms were placed in calculated positions and included in a riding-model approximation with C—H distances ranging from 0.95 to 0.99 Å and Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl). The water H atoms were located in a difference Fourier map and refined with the restraint O-H = 0.85 (2)Å.
Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./lh5085fig1thm.gif)
| Fig. 1. The asymmetric unit of the title compound. Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level. |
![[Figure 2]](./lh5085fig2thm.gif)
| Fig. 2. Part of the crystal structure of the title compound, showing hydrogen bonds as dashed lines. Only H atoms involved in hydrogen bonging are shown. |
| [Ni(C27H27N7)(C3H7NO)(H2O)](C6H2N3O7)2 | Z = 2 |
| Mr = 1055.57 | F(000) = 1092 |
| Triclinic, P1 | Dx = 1.545 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 12.0768 (3) Å | Cell parameters from 8420 reflections |
| b = 13.2619 (4) Å | θ = 2.4–28.2° |
| c = 15.3544 (4) Å | µ = 0.52 mm−1 |
| α = 108.583 (1)° | T = 153 K |
| β = 95.703 (1)° | Block, green |
| γ = 99.506 (1)° | 0.25 × 0.22 × 0.11 mm |
| V = 2268.36 (11) Å3 |
| Bruker SMART APEXII diffractometer | 8420 independent reflections |
| Radiation source: fine-focus sealed tube | 5743 reflections with I > 2σ(I) |
| graphite | Rint = 0.041 |
| ω scans | θmax = 25.5°, θmin = 3.1° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
| Tmin = 0.882, Tmax = 0.945 | k = −16→16 |
| 18738 measured reflections | l = −17→18 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.159 | w = 1/[σ2(Fo2) + (0.0452P)2 + 5.4011P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.18 | (Δ/σ)max = 0.001 |
| 8420 reflections | Δρmax = 1.01 e Å−3 |
| 667 parameters | Δρmin = −1.24 e Å−3 |
| 2 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0026 (5) |
| [Ni(C27H27N7)(C3H7NO)(H2O)](C6H2N3O7)2 | γ = 99.506 (1)° |
| Mr = 1055.57 | V = 2268.36 (11) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 12.0768 (3) Å | Mo Kα radiation |
| b = 13.2619 (4) Å | µ = 0.52 mm−1 |
| c = 15.3544 (4) Å | T = 153 K |
| α = 108.583 (1)° | 0.25 × 0.22 × 0.11 mm |
| β = 95.703 (1)° |
| Bruker SMART APEXII diffractometer | 8420 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5743 reflections with I > 2σ(I) |
| Tmin = 0.882, Tmax = 0.945 | Rint = 0.041 |
| 18738 measured reflections | θmax = 25.5° |
| R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.159 | Δρmax = 1.01 e Å−3 |
| S = 1.18 | Δρmin = −1.24 e Å−3 |
| 8420 reflections | Absolute structure: ? |
| 667 parameters | Flack parameter: ? |
| 2 restraints | Rogers parameter: ? |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| Ni | 0.46074 (4) | 0.67214 (4) | 0.72572 (4) | 0.02153 (16) | |
| O1 | 0.3577 (2) | 0.7136 (2) | 0.63281 (19) | 0.0281 (7) | |
| O2 | 0.5213 (3) | 0.5564 (3) | 0.6231 (2) | 0.0274 (7) | |
| O3 | 0.6467 (3) | 0.6084 (3) | 0.5008 (2) | 0.0476 (10) | |
| O4 | 0.5367 (3) | 0.6964 (4) | 0.3971 (3) | 0.0792 (14) | |
| O5 | 0.5862 (5) | 0.8686 (5) | 0.4310 (4) | 0.108 (2) | |
| O6 | 0.9546 (4) | 1.0643 (3) | 0.5816 (3) | 0.0661 (13) | |
| O7 | 1.0726 (4) | 0.9877 (4) | 0.6429 (3) | 0.0731 (14) | |
| O8 | 0.9680 (4) | 0.6105 (4) | 0.5949 (4) | 0.0919 (17) | |
| O9 | 0.7967 (4) | 0.5556 (4) | 0.6107 (4) | 0.0843 (15) | |
| O10 | 0.2350 (3) | 0.3427 (3) | 0.9903 (2) | 0.0412 (8) | |
| O11 | 0.3778 (3) | 0.5213 (3) | 0.9850 (2) | 0.0486 (10) | |
| O12 | 0.2960 (3) | 0.6577 (4) | 1.0118 (3) | 0.0670 (12) | |
| O13 | −0.0696 (3) | 0.6005 (3) | 0.8309 (3) | 0.0503 (9) | |
| O14 | −0.1952 (3) | 0.4559 (3) | 0.8155 (2) | 0.0456 (9) | |
| O15 | −0.0703 (4) | 0.2009 (4) | 0.9669 (3) | 0.0758 (14) | |
| O16 | 0.0677 (4) | 0.1511 (3) | 0.8988 (4) | 0.0825 (16) | |
| N1 | 0.6052 (3) | 0.7868 (3) | 0.7367 (2) | 0.0237 (7) | |
| N2 | 0.7876 (3) | 0.8539 (3) | 0.7984 (2) | 0.0234 (8) | |
| N3 | 0.3619 (3) | 0.5380 (3) | 0.7390 (2) | 0.0237 (8) | |
| N4 | 0.3585 (3) | 0.3892 (3) | 0.7762 (2) | 0.0248 (8) | |
| N5 | 0.4158 (3) | 0.7756 (3) | 0.8396 (2) | 0.0237 (8) | |
| N6 | 0.4450 (3) | 0.8522 (3) | 0.9935 (2) | 0.0251 (8) | |
| N7 | 0.5741 (3) | 0.6426 (3) | 0.8305 (2) | 0.0206 (7) | |
| N8 | 0.2926 (3) | 0.7234 (3) | 0.4929 (2) | 0.0321 (9) | |
| N9 | 0.6035 (4) | 0.7845 (5) | 0.4381 (3) | 0.0539 (13) | |
| N10 | 0.9804 (4) | 0.9860 (4) | 0.5993 (3) | 0.0495 (12) | |
| N11 | 0.8678 (4) | 0.6177 (4) | 0.5921 (3) | 0.0481 (11) | |
| N12 | 0.2919 (3) | 0.5600 (4) | 0.9830 (3) | 0.0397 (10) | |
| N13 | −0.0966 (3) | 0.5105 (3) | 0.8384 (3) | 0.0349 (9) | |
| N14 | 0.0128 (4) | 0.2193 (4) | 0.9307 (3) | 0.0484 (12) | |
| C1 | 0.6383 (3) | 0.8840 (3) | 0.7211 (3) | 0.0231 (9) | |
| C2 | 0.5753 (4) | 0.9402 (3) | 0.6782 (3) | 0.0281 (10) | |
| H2B | 0.4972 | 0.9119 | 0.6520 | 0.034* | |
| C3 | 0.6314 (4) | 1.0377 (4) | 0.6758 (3) | 0.0357 (11) | |
| H3A | 0.5911 | 1.0781 | 0.6477 | 0.043* | |
| C4 | 0.7468 (4) | 1.0795 (4) | 0.7138 (4) | 0.0380 (11) | |
| H4A | 0.7826 | 1.1472 | 0.7103 | 0.046* | |
| C5 | 0.8102 (4) | 1.0252 (4) | 0.7563 (3) | 0.0339 (11) | |
| H5A | 0.8883 | 1.0535 | 0.7822 | 0.041* | |
| C6 | 0.7524 (3) | 0.9264 (3) | 0.7589 (3) | 0.0255 (9) | |
| C7 | 0.6969 (3) | 0.7732 (3) | 0.7840 (3) | 0.0232 (9) | |
| C8 | 0.6925 (3) | 0.6766 (3) | 0.8150 (3) | 0.0250 (9) | |
| H8A | 0.7136 | 0.6163 | 0.7667 | 0.030* | |
| H8B | 0.7468 | 0.6956 | 0.8733 | 0.030* | |
| C9 | 0.5451 (3) | 0.5244 (3) | 0.8168 (3) | 0.0262 (9) | |
| H9A | 0.5623 | 0.5127 | 0.8768 | 0.031* | |
| H9B | 0.5903 | 0.4844 | 0.7727 | 0.031* | |
| C10 | 0.4205 (3) | 0.4843 (3) | 0.7788 (3) | 0.0248 (9) | |
| C11 | 0.2494 (3) | 0.3800 (3) | 0.7303 (3) | 0.0230 (9) | |
| C12 | 0.1523 (4) | 0.2984 (4) | 0.7074 (3) | 0.0305 (10) | |
| H12A | 0.1515 | 0.2337 | 0.7218 | 0.037* | |
| C13 | 0.0562 (4) | 0.3171 (4) | 0.6622 (3) | 0.0318 (10) | |
| H13A | −0.0127 | 0.2640 | 0.6453 | 0.038* | |
| C14 | 0.0588 (4) | 0.4132 (4) | 0.6410 (3) | 0.0318 (10) | |
| H14A | −0.0084 | 0.4232 | 0.6100 | 0.038* | |
| C15 | 0.1555 (3) | 0.4924 (3) | 0.6637 (3) | 0.0265 (9) | |
| H15A | 0.1565 | 0.5572 | 0.6496 | 0.032* | |
| C16 | 0.2530 (3) | 0.4742 (3) | 0.7088 (3) | 0.0232 (9) | |
| C17 | 0.5556 (4) | 0.7092 (4) | 0.9249 (3) | 0.0279 (10) | |
| H17A | 0.5276 | 0.6601 | 0.9585 | 0.033* | |
| H17B | 0.6291 | 0.7560 | 0.9610 | 0.033* | |
| C18 | 0.4724 (3) | 0.7786 (3) | 0.9191 (3) | 0.0221 (9) | |
| C19 | 0.3643 (3) | 0.8988 (3) | 0.9595 (3) | 0.0263 (9) | |
| C20 | 0.3085 (4) | 0.9796 (4) | 1.0048 (3) | 0.0350 (11) | |
| H20A | 0.3210 | 1.0117 | 1.0707 | 0.042* | |
| C21 | 0.2339 (4) | 1.0103 (4) | 0.9487 (3) | 0.0344 (11) | |
| H21A | 0.1947 | 1.0658 | 0.9765 | 0.041* | |
| C22 | 0.2151 (4) | 0.9617 (4) | 0.8520 (3) | 0.0360 (11) | |
| H22A | 0.1627 | 0.9845 | 0.8158 | 0.043* | |
| C23 | 0.2704 (3) | 0.8811 (4) | 0.8072 (3) | 0.0313 (10) | |
| H23A | 0.2569 | 0.8482 | 0.7413 | 0.038* | |
| C24 | 0.3464 (3) | 0.8508 (3) | 0.8632 (3) | 0.0233 (9) | |
| C25 | 0.9037 (4) | 0.8644 (4) | 0.8443 (3) | 0.0360 (11) | |
| H25A | 0.9067 | 0.8029 | 0.8661 | 0.054* | |
| H25B | 0.9253 | 0.9326 | 0.8975 | 0.054* | |
| H25C | 0.9567 | 0.8648 | 0.7999 | 0.054* | |
| C26 | 0.3955 (4) | 0.3098 (4) | 0.8132 (3) | 0.0334 (10) | |
| H26A | 0.4758 | 0.3358 | 0.8419 | 0.050* | |
| H26B | 0.3863 | 0.2402 | 0.7625 | 0.050* | |
| H26C | 0.3494 | 0.2999 | 0.8600 | 0.050* | |
| C27 | 0.4860 (4) | 0.8732 (4) | 1.0919 (3) | 0.0327 (10) | |
| H27A | 0.5429 | 0.8297 | 1.0971 | 0.049* | |
| H27B | 0.4221 | 0.8534 | 1.1220 | 0.049* | |
| H27C | 0.5205 | 0.9506 | 1.1226 | 0.049* | |
| C28 | 0.3449 (3) | 0.6785 (3) | 0.5465 (3) | 0.0247 (9) | |
| H28A | 0.3740 | 0.6161 | 0.5172 | 0.030* | |
| C29 | 0.2483 (7) | 0.8196 (6) | 0.5310 (4) | 0.088 (3) | |
| H29A | 0.2621 | 0.8427 | 0.5992 | 0.132* | |
| H29B | 0.1662 | 0.8037 | 0.5087 | 0.132* | |
| H29C | 0.2862 | 0.8778 | 0.5112 | 0.132* | |
| C30 | 0.2785 (4) | 0.6789 (4) | 0.3916 (3) | 0.0319 (10) | |
| H30A | 0.3109 | 0.6136 | 0.3730 | 0.048* | |
| H30B | 0.3177 | 0.7333 | 0.3682 | 0.048* | |
| H30C | 0.1973 | 0.6598 | 0.3656 | 0.048* | |
| C31 | 0.7227 (4) | 0.6930 (4) | 0.5180 (3) | 0.0322 (10) | |
| C32 | 0.7101 (4) | 0.7865 (4) | 0.4924 (3) | 0.0310 (10) | |
| C33 | 0.7918 (4) | 0.8803 (4) | 0.5177 (3) | 0.0354 (11) | |
| H33A | 0.7775 | 0.9406 | 0.5010 | 0.042* | |
| C34 | 0.8956 (4) | 0.8854 (4) | 0.5681 (3) | 0.0311 (10) | |
| C35 | 0.9189 (4) | 0.7981 (4) | 0.5902 (3) | 0.0323 (10) | |
| H35A | 0.9920 | 0.8014 | 0.6216 | 0.039* | |
| C36 | 0.8360 (4) | 0.7063 (4) | 0.5667 (3) | 0.0302 (10) | |
| C37 | 0.1626 (4) | 0.3812 (4) | 0.9551 (3) | 0.0298 (10) | |
| C38 | 0.1809 (3) | 0.4884 (4) | 0.9463 (3) | 0.0313 (10) | |
| C39 | 0.0991 (4) | 0.5297 (4) | 0.9091 (3) | 0.0294 (10) | |
| H39A | 0.1170 | 0.6003 | 0.9048 | 0.035* | |
| C40 | −0.0101 (3) | 0.4675 (4) | 0.8779 (3) | 0.0275 (10) | |
| C41 | −0.0389 (4) | 0.3658 (4) | 0.8866 (3) | 0.0326 (11) | |
| H41A | −0.1149 | 0.3250 | 0.8678 | 0.039* | |
| C42 | 0.0447 (4) | 0.3260 (4) | 0.9229 (3) | 0.0291 (10) | |
| H2D | 0.569 (4) | 0.575 (5) | 0.590 (4) | 0.07 (2)* | |
| H2C | 0.479 (5) | 0.496 (3) | 0.590 (4) | 0.10 (3)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni | 0.0232 (3) | 0.0219 (3) | 0.0210 (3) | 0.0076 (2) | 0.0037 (2) | 0.0080 (2) |
| O1 | 0.0310 (15) | 0.0346 (17) | 0.0204 (15) | 0.0126 (13) | 0.0020 (12) | 0.0098 (13) |
| O2 | 0.0276 (16) | 0.0270 (17) | 0.0267 (16) | 0.0038 (14) | 0.0095 (14) | 0.0075 (14) |
| O3 | 0.054 (2) | 0.044 (2) | 0.0298 (18) | −0.0176 (18) | 0.0120 (16) | 0.0046 (16) |
| O4 | 0.042 (2) | 0.099 (4) | 0.079 (3) | 0.006 (3) | −0.011 (2) | 0.017 (3) |
| O5 | 0.125 (5) | 0.082 (4) | 0.100 (4) | 0.054 (4) | −0.051 (3) | 0.014 (3) |
| O6 | 0.102 (3) | 0.024 (2) | 0.072 (3) | −0.002 (2) | 0.042 (3) | 0.0137 (19) |
| O7 | 0.061 (3) | 0.074 (3) | 0.059 (3) | −0.031 (2) | −0.011 (2) | 0.018 (2) |
| O8 | 0.082 (3) | 0.098 (4) | 0.131 (5) | 0.051 (3) | 0.016 (3) | 0.070 (4) |
| O9 | 0.105 (4) | 0.055 (3) | 0.112 (4) | 0.008 (3) | 0.020 (3) | 0.058 (3) |
| O10 | 0.0372 (18) | 0.059 (2) | 0.0392 (19) | 0.0253 (17) | 0.0060 (15) | 0.0247 (17) |
| O11 | 0.0251 (17) | 0.081 (3) | 0.045 (2) | 0.0168 (18) | 0.0085 (15) | 0.025 (2) |
| O12 | 0.043 (2) | 0.049 (3) | 0.102 (4) | −0.0030 (19) | 0.006 (2) | 0.025 (2) |
| O13 | 0.051 (2) | 0.055 (2) | 0.059 (2) | 0.0289 (19) | 0.0080 (18) | 0.030 (2) |
| O14 | 0.0326 (18) | 0.056 (2) | 0.043 (2) | 0.0185 (17) | −0.0091 (15) | 0.0090 (17) |
| O15 | 0.099 (4) | 0.049 (3) | 0.073 (3) | −0.007 (3) | 0.019 (3) | 0.022 (2) |
| O16 | 0.064 (3) | 0.041 (2) | 0.135 (4) | 0.026 (2) | −0.011 (3) | 0.019 (3) |
| N1 | 0.0284 (18) | 0.0211 (18) | 0.0252 (18) | 0.0109 (15) | 0.0071 (15) | 0.0093 (15) |
| N2 | 0.0169 (16) | 0.0262 (19) | 0.0242 (18) | 0.0012 (14) | 0.0002 (14) | 0.0071 (15) |
| N3 | 0.0206 (16) | 0.0245 (19) | 0.0245 (18) | 0.0066 (14) | 0.0024 (14) | 0.0058 (15) |
| N4 | 0.0297 (18) | 0.0213 (18) | 0.0274 (19) | 0.0073 (15) | 0.0054 (15) | 0.0125 (15) |
| N5 | 0.0228 (17) | 0.0254 (19) | 0.0249 (18) | 0.0103 (15) | 0.0053 (14) | 0.0080 (15) |
| N6 | 0.0285 (18) | 0.0266 (19) | 0.0189 (17) | 0.0102 (15) | 0.0052 (14) | 0.0033 (15) |
| N7 | 0.0196 (16) | 0.0240 (18) | 0.0198 (17) | 0.0060 (14) | 0.0024 (13) | 0.0091 (14) |
| N8 | 0.040 (2) | 0.033 (2) | 0.0263 (19) | 0.0138 (18) | 0.0021 (16) | 0.0118 (17) |
| N9 | 0.051 (3) | 0.071 (4) | 0.035 (2) | 0.027 (3) | 0.004 (2) | 0.006 (2) |
| N10 | 0.067 (3) | 0.030 (2) | 0.042 (3) | −0.010 (2) | 0.019 (2) | 0.007 (2) |
| N11 | 0.065 (3) | 0.036 (3) | 0.051 (3) | 0.015 (2) | 0.011 (2) | 0.023 (2) |
| N12 | 0.032 (2) | 0.052 (3) | 0.041 (2) | 0.008 (2) | 0.0115 (18) | 0.022 (2) |
| N13 | 0.042 (2) | 0.043 (2) | 0.027 (2) | 0.025 (2) | 0.0044 (17) | 0.0135 (18) |
| N14 | 0.051 (3) | 0.035 (3) | 0.050 (3) | 0.011 (2) | −0.013 (2) | 0.007 (2) |
| C1 | 0.022 (2) | 0.020 (2) | 0.026 (2) | 0.0019 (17) | 0.0052 (17) | 0.0065 (17) |
| C2 | 0.035 (2) | 0.027 (2) | 0.026 (2) | 0.0087 (19) | 0.0065 (19) | 0.0117 (19) |
| C3 | 0.045 (3) | 0.030 (3) | 0.037 (3) | 0.013 (2) | 0.008 (2) | 0.015 (2) |
| C4 | 0.040 (3) | 0.025 (2) | 0.051 (3) | 0.001 (2) | 0.010 (2) | 0.019 (2) |
| C5 | 0.032 (2) | 0.028 (2) | 0.039 (3) | 0.004 (2) | 0.006 (2) | 0.008 (2) |
| C6 | 0.029 (2) | 0.024 (2) | 0.023 (2) | 0.0092 (18) | 0.0070 (18) | 0.0060 (18) |
| C7 | 0.030 (2) | 0.024 (2) | 0.021 (2) | 0.0123 (18) | 0.0068 (17) | 0.0095 (17) |
| C8 | 0.022 (2) | 0.031 (2) | 0.025 (2) | 0.0084 (18) | 0.0023 (17) | 0.0122 (18) |
| C9 | 0.028 (2) | 0.026 (2) | 0.032 (2) | 0.0118 (18) | 0.0046 (18) | 0.0161 (19) |
| C10 | 0.028 (2) | 0.024 (2) | 0.025 (2) | 0.0130 (18) | 0.0053 (17) | 0.0083 (18) |
| C11 | 0.028 (2) | 0.024 (2) | 0.021 (2) | 0.0064 (17) | 0.0108 (17) | 0.0094 (17) |
| C12 | 0.032 (2) | 0.025 (2) | 0.038 (3) | 0.0050 (19) | 0.013 (2) | 0.013 (2) |
| C13 | 0.029 (2) | 0.029 (2) | 0.040 (3) | 0.0050 (19) | 0.011 (2) | 0.014 (2) |
| C14 | 0.024 (2) | 0.036 (3) | 0.035 (2) | 0.0061 (19) | 0.0025 (19) | 0.012 (2) |
| C15 | 0.027 (2) | 0.023 (2) | 0.033 (2) | 0.0069 (18) | 0.0065 (18) | 0.0112 (19) |
| C16 | 0.029 (2) | 0.021 (2) | 0.023 (2) | 0.0065 (17) | 0.0099 (17) | 0.0100 (17) |
| C17 | 0.033 (2) | 0.033 (2) | 0.020 (2) | 0.0121 (19) | 0.0049 (18) | 0.0085 (18) |
| C18 | 0.024 (2) | 0.025 (2) | 0.021 (2) | 0.0069 (17) | 0.0024 (16) | 0.0121 (17) |
| C19 | 0.028 (2) | 0.024 (2) | 0.029 (2) | 0.0096 (18) | 0.0071 (18) | 0.0091 (18) |
| C20 | 0.036 (2) | 0.039 (3) | 0.028 (2) | 0.015 (2) | 0.010 (2) | 0.004 (2) |
| C21 | 0.037 (2) | 0.037 (3) | 0.034 (3) | 0.026 (2) | 0.009 (2) | 0.009 (2) |
| C22 | 0.031 (2) | 0.042 (3) | 0.039 (3) | 0.019 (2) | 0.007 (2) | 0.014 (2) |
| C23 | 0.026 (2) | 0.036 (3) | 0.028 (2) | 0.0089 (19) | 0.0006 (18) | 0.005 (2) |
| C24 | 0.0205 (19) | 0.024 (2) | 0.024 (2) | 0.0066 (17) | 0.0040 (16) | 0.0046 (17) |
| C25 | 0.030 (2) | 0.042 (3) | 0.036 (3) | 0.010 (2) | 0.001 (2) | 0.014 (2) |
| C26 | 0.039 (3) | 0.029 (2) | 0.037 (3) | 0.010 (2) | 0.006 (2) | 0.017 (2) |
| C27 | 0.042 (3) | 0.035 (3) | 0.017 (2) | 0.010 (2) | 0.0013 (19) | 0.0035 (19) |
| C28 | 0.027 (2) | 0.023 (2) | 0.029 (2) | 0.0078 (18) | 0.0027 (18) | 0.0147 (18) |
| C29 | 0.139 (7) | 0.097 (6) | 0.041 (3) | 0.098 (5) | −0.003 (4) | 0.010 (3) |
| C30 | 0.035 (2) | 0.042 (3) | 0.021 (2) | 0.004 (2) | 0.0017 (18) | 0.017 (2) |
| C31 | 0.036 (2) | 0.031 (3) | 0.027 (2) | 0.002 (2) | 0.017 (2) | 0.006 (2) |
| C32 | 0.032 (2) | 0.040 (3) | 0.024 (2) | 0.017 (2) | 0.0084 (18) | 0.010 (2) |
| C33 | 0.052 (3) | 0.033 (3) | 0.028 (2) | 0.014 (2) | 0.014 (2) | 0.015 (2) |
| C34 | 0.038 (2) | 0.021 (2) | 0.031 (2) | −0.0034 (19) | 0.011 (2) | 0.0076 (19) |
| C35 | 0.032 (2) | 0.034 (3) | 0.030 (2) | 0.006 (2) | 0.0072 (19) | 0.009 (2) |
| C36 | 0.042 (3) | 0.026 (2) | 0.029 (2) | 0.012 (2) | 0.011 (2) | 0.0151 (19) |
| C37 | 0.033 (2) | 0.040 (3) | 0.022 (2) | 0.021 (2) | 0.0073 (18) | 0.011 (2) |
| C38 | 0.024 (2) | 0.045 (3) | 0.027 (2) | 0.012 (2) | 0.0035 (18) | 0.013 (2) |
| C39 | 0.036 (2) | 0.035 (3) | 0.024 (2) | 0.015 (2) | 0.0112 (19) | 0.0133 (19) |
| C40 | 0.030 (2) | 0.036 (3) | 0.023 (2) | 0.020 (2) | 0.0046 (18) | 0.0118 (19) |
| C41 | 0.035 (2) | 0.034 (3) | 0.025 (2) | 0.015 (2) | 0.0026 (19) | 0.001 (2) |
| C42 | 0.035 (2) | 0.029 (2) | 0.029 (2) | 0.017 (2) | 0.0036 (19) | 0.0129 (19) |
| Ni—N5 | 2.035 (3) | C8—H8A | 0.9900 |
| Ni—N3 | 2.052 (4) | C8—H8B | 0.9900 |
| Ni—O1 | 2.063 (3) | C9—C10 | 1.500 (6) |
| Ni—N1 | 2.071 (3) | C9—H9A | 0.9900 |
| Ni—O2 | 2.106 (3) | C9—H9B | 0.9900 |
| Ni—N7 | 2.181 (3) | C11—C16 | 1.384 (6) |
| O1—C28 | 1.240 (5) | C11—C12 | 1.388 (6) |
| O2—H2D | 0.86 (2) | C12—C13 | 1.391 (6) |
| O2—H2C | 0.85 (2) | C12—H12A | 0.9500 |
| O3—O3 | 0.000 (9) | C13—C14 | 1.409 (6) |
| O3—C31 | 1.263 (5) | C13—H13A | 0.9500 |
| O4—N9 | 1.237 (6) | C14—C15 | 1.366 (6) |
| O5—N9 | 1.204 (7) | C14—H14A | 0.9500 |
| O6—N10 | 1.232 (6) | C15—C16 | 1.401 (6) |
| O7—N10 | 1.234 (6) | C15—H15A | 0.9500 |
| O8—N11 | 1.227 (6) | C17—C18 | 1.485 (6) |
| O9—N11 | 1.209 (6) | C17—H17A | 0.9900 |
| O10—C37 | 1.244 (5) | C17—H17B | 0.9900 |
| O11—N12 | 1.233 (5) | C19—C24 | 1.389 (6) |
| O12—N12 | 1.219 (6) | C19—C20 | 1.394 (6) |
| O13—N13 | 1.230 (5) | C20—C21 | 1.382 (6) |
| O14—N13 | 1.239 (5) | C20—H20A | 0.9500 |
| O15—N14 | 1.221 (6) | C21—C22 | 1.395 (6) |
| O16—N14 | 1.216 (6) | C21—H21A | 0.9500 |
| N1—C7 | 1.333 (5) | C22—C23 | 1.385 (6) |
| N1—C1 | 1.387 (5) | C22—H22A | 0.9500 |
| N2—C7 | 1.345 (5) | C23—C24 | 1.390 (6) |
| N2—C6 | 1.388 (5) | C23—H23A | 0.9500 |
| N2—C25 | 1.470 (5) | C25—H25A | 0.9800 |
| N3—C10 | 1.318 (5) | C25—H25B | 0.9800 |
| N3—C16 | 1.387 (5) | C25—H25C | 0.9800 |
| N4—C10 | 1.343 (5) | C26—H26A | 0.9800 |
| N4—C11 | 1.399 (5) | C26—H26B | 0.9800 |
| N4—C26 | 1.455 (5) | C26—H26C | 0.9800 |
| N5—C18 | 1.324 (5) | C27—H27A | 0.9800 |
| N5—C24 | 1.390 (5) | C27—H27B | 0.9800 |
| N6—C18 | 1.355 (5) | C27—H27C | 0.9800 |
| N6—C19 | 1.381 (5) | C28—H28A | 0.9500 |
| N6—C27 | 1.465 (5) | C29—H29A | 0.9800 |
| N7—C9 | 1.490 (5) | C29—H29B | 0.9800 |
| N7—C8 | 1.493 (5) | C29—H29C | 0.9800 |
| N7—C17 | 1.498 (5) | C30—H30A | 0.9800 |
| N8—C28 | 1.329 (5) | C30—H30B | 0.9800 |
| N8—C29 | 1.438 (7) | C30—H30C | 0.9800 |
| N8—C30 | 1.457 (5) | C31—O3 | 1.263 (5) |
| N9—C32 | 1.454 (6) | C31—C32 | 1.441 (7) |
| N10—C34 | 1.450 (6) | C31—C36 | 1.447 (6) |
| N11—C36 | 1.446 (6) | C32—C33 | 1.372 (7) |
| N12—C38 | 1.450 (6) | C33—C34 | 1.386 (7) |
| N13—C40 | 1.441 (5) | C33—H33A | 0.9500 |
| N14—C42 | 1.450 (6) | C34—C35 | 1.369 (6) |
| C1—C6 | 1.388 (6) | C35—C36 | 1.364 (6) |
| C1—C2 | 1.403 (6) | C35—H35A | 0.9500 |
| C2—C3 | 1.371 (6) | C37—C42 | 1.446 (6) |
| C2—H2B | 0.9500 | C37—C38 | 1.454 (7) |
| C3—C4 | 1.403 (7) | C38—C39 | 1.367 (6) |
| C3—H3A | 0.9500 | C39—C40 | 1.382 (6) |
| C4—C5 | 1.383 (7) | C39—H39A | 0.9500 |
| C4—H4A | 0.9500 | C40—C41 | 1.388 (7) |
| C5—C6 | 1.394 (6) | C41—C42 | 1.363 (6) |
| C5—H5A | 0.9500 | C41—H41A | 0.9500 |
| C7—C8 | 1.498 (6) | ||
| N5—Ni—N3 | 92.81 (14) | C14—C13—H13A | 119.3 |
| N5—Ni—O1 | 93.80 (12) | C15—C14—C13 | 121.8 (4) |
| N3—Ni—O1 | 104.09 (12) | C15—C14—H14A | 119.1 |
| N5—Ni—N1 | 90.52 (13) | C13—C14—H14A | 119.1 |
| N3—Ni—N1 | 158.76 (13) | C14—C15—C16 | 117.4 (4) |
| O1—Ni—N1 | 96.60 (13) | C14—C15—H15A | 121.3 |
| N5—Ni—O2 | 170.87 (13) | C16—C15—H15A | 121.3 |
| N3—Ni—O2 | 84.00 (13) | C11—C16—N3 | 109.2 (4) |
| O1—Ni—O2 | 95.28 (12) | C11—C16—C15 | 120.5 (4) |
| N1—Ni—O2 | 89.44 (13) | N3—C16—C15 | 130.3 (4) |
| N5—Ni—N7 | 82.85 (13) | C18—C17—N7 | 112.0 (3) |
| N3—Ni—N7 | 79.47 (12) | C18—C17—H17A | 109.2 |
| O1—Ni—N7 | 175.27 (12) | N7—C17—H17A | 109.2 |
| N1—Ni—N7 | 80.16 (13) | C18—C17—H17B | 109.2 |
| O2—Ni—N7 | 88.15 (12) | N7—C17—H17B | 109.2 |
| C28—O1—Ni | 128.2 (3) | H17A—C17—H17B | 107.9 |
| Ni—O2—H2D | 122 (4) | N5—C18—N6 | 111.8 (3) |
| Ni—O2—H2C | 121 (5) | N5—C18—C17 | 123.5 (4) |
| H2D—O2—H2C | 108 (6) | N6—C18—C17 | 124.7 (3) |
| O3—O3—C31 | 0(10) | N6—C19—C24 | 106.3 (3) |
| C7—N1—C1 | 105.8 (3) | N6—C19—C20 | 131.3 (4) |
| C7—N1—Ni | 112.8 (3) | C24—C19—C20 | 122.3 (4) |
| C1—N1—Ni | 140.8 (3) | C21—C20—C19 | 116.4 (4) |
| C7—N2—C6 | 106.9 (3) | C21—C20—H20A | 121.8 |
| C7—N2—C25 | 127.8 (4) | C19—C20—H20A | 121.8 |
| C6—N2—C25 | 125.3 (4) | C20—C21—C22 | 121.4 (4) |
| C10—N3—C16 | 105.7 (4) | C20—C21—H21A | 119.3 |
| C10—N3—Ni | 113.2 (3) | C22—C21—H21A | 119.3 |
| C16—N3—Ni | 140.4 (3) | C23—C22—C21 | 122.1 (4) |
| C10—N4—C11 | 106.6 (3) | C23—C22—H22A | 119.0 |
| C10—N4—C26 | 127.6 (3) | C21—C22—H22A | 119.0 |
| C11—N4—C26 | 125.8 (3) | C22—C23—C24 | 116.8 (4) |
| C18—N5—C24 | 106.2 (3) | C22—C23—H23A | 121.6 |
| C18—N5—Ni | 113.2 (3) | C24—C23—H23A | 121.6 |
| C24—N5—Ni | 140.6 (3) | C19—C24—C23 | 121.0 (4) |
| C18—N6—C19 | 107.2 (3) | C19—C24—N5 | 108.5 (3) |
| C18—N6—C27 | 126.9 (4) | C23—C24—N5 | 130.5 (4) |
| C19—N6—C27 | 125.8 (3) | N2—C25—H25A | 109.5 |
| C9—N7—C8 | 111.9 (3) | N2—C25—H25B | 109.5 |
| C9—N7—C17 | 110.7 (3) | H25A—C25—H25B | 109.5 |
| C8—N7—C17 | 111.3 (3) | N2—C25—H25C | 109.5 |
| C9—N7—Ni | 107.7 (2) | H25A—C25—H25C | 109.5 |
| C8—N7—Ni | 106.6 (2) | H25B—C25—H25C | 109.5 |
| C17—N7—Ni | 108.4 (2) | N4—C26—H26A | 109.5 |
| C28—N8—C29 | 122.1 (4) | N4—C26—H26B | 109.5 |
| C28—N8—C30 | 121.8 (4) | H26A—C26—H26B | 109.5 |
| C29—N8—C30 | 116.0 (4) | N4—C26—H26C | 109.5 |
| O5—N9—O4 | 122.3 (5) | H26A—C26—H26C | 109.5 |
| O5—N9—C32 | 118.3 (5) | H26B—C26—H26C | 109.5 |
| O4—N9—C32 | 119.3 (5) | N6—C27—H27A | 109.5 |
| O6—N10—O7 | 124.6 (5) | N6—C27—H27B | 109.5 |
| O6—N10—C34 | 117.6 (5) | H27A—C27—H27B | 109.5 |
| O7—N10—C34 | 117.7 (5) | N6—C27—H27C | 109.5 |
| O9—N11—O8 | 122.9 (5) | H27A—C27—H27C | 109.5 |
| O9—N11—C36 | 119.7 (5) | H27B—C27—H27C | 109.5 |
| O8—N11—C36 | 117.4 (5) | O1—C28—N8 | 123.7 (4) |
| O12—N12—O11 | 122.3 (4) | O1—C28—H28A | 118.2 |
| O12—N12—C38 | 117.8 (4) | N8—C28—H28A | 118.2 |
| O11—N12—C38 | 119.9 (4) | N8—C29—H29A | 109.5 |
| O13—N13—O14 | 123.1 (4) | N8—C29—H29B | 109.5 |
| O13—N13—C40 | 118.5 (4) | H29A—C29—H29B | 109.5 |
| O14—N13—C40 | 118.4 (4) | N8—C29—H29C | 109.5 |
| O16—N14—O15 | 122.8 (5) | H29A—C29—H29C | 109.5 |
| O16—N14—C42 | 118.8 (5) | H29B—C29—H29C | 109.5 |
| O15—N14—C42 | 118.4 (5) | N8—C30—H30A | 109.5 |
| N1—C1—C6 | 108.8 (4) | N8—C30—H30B | 109.5 |
| N1—C1—C2 | 130.5 (4) | H30A—C30—H30B | 109.5 |
| C6—C1—C2 | 120.8 (4) | N8—C30—H30C | 109.5 |
| C3—C2—C1 | 117.0 (4) | H30A—C30—H30C | 109.5 |
| C3—C2—H2B | 121.5 | H30B—C30—H30C | 109.5 |
| C1—C2—H2B | 121.5 | O3—C31—O3 | 0.0 (4) |
| C2—C3—C4 | 121.7 (4) | O3—C31—C32 | 125.8 (4) |
| C2—C3—H3A | 119.1 | O3—C31—C32 | 125.8 (4) |
| C4—C3—H3A | 119.1 | O3—C31—C36 | 122.6 (4) |
| C5—C4—C3 | 122.0 (4) | O3—C31—C36 | 122.6 (4) |
| C5—C4—H4A | 119.0 | C32—C31—C36 | 111.6 (4) |
| C3—C4—H4A | 119.0 | C33—C32—C31 | 124.4 (4) |
| C4—C5—C6 | 115.9 (4) | C33—C32—N9 | 116.6 (5) |
| C4—C5—H5A | 122.0 | C31—C32—N9 | 119.0 (4) |
| C6—C5—H5A | 122.0 | C32—C33—C34 | 118.7 (4) |
| N2—C6—C1 | 106.2 (4) | C32—C33—H33A | 120.7 |
| N2—C6—C5 | 131.1 (4) | C34—C33—H33A | 120.7 |
| C1—C6—C5 | 122.6 (4) | C35—C34—C33 | 121.4 (4) |
| N1—C7—N2 | 112.3 (4) | C35—C34—N10 | 119.4 (4) |
| N1—C7—C8 | 120.9 (4) | C33—C34—N10 | 119.1 (4) |
| N2—C7—C8 | 126.8 (3) | C36—C35—C34 | 119.2 (4) |
| N7—C8—C7 | 108.1 (3) | C36—C35—H35A | 120.4 |
| N7—C8—H8A | 110.1 | C34—C35—H35A | 120.4 |
| C7—C8—H8A | 110.1 | C35—C36—N11 | 115.7 (4) |
| N7—C8—H8B | 110.1 | C35—C36—C31 | 124.5 (4) |
| C7—C8—H8B | 110.1 | N11—C36—C31 | 119.8 (4) |
| H8A—C8—H8B | 108.4 | O10—C37—C42 | 123.3 (4) |
| N7—C9—C10 | 107.8 (3) | O10—C37—C38 | 125.8 (4) |
| N7—C9—H9A | 110.1 | C42—C37—C38 | 110.7 (4) |
| C10—C9—H9A | 110.1 | C39—C38—N12 | 116.6 (4) |
| N7—C9—H9B | 110.1 | C39—C38—C37 | 124.7 (4) |
| C10—C9—H9B | 110.1 | N12—C38—C37 | 118.7 (4) |
| H9A—C9—H9B | 108.5 | C38—C39—C40 | 119.2 (4) |
| N3—C10—N4 | 112.9 (4) | C38—C39—H39A | 120.4 |
| N3—C10—C9 | 122.2 (4) | C40—C39—H39A | 120.4 |
| N4—C10—C9 | 124.8 (4) | C39—C40—C41 | 121.3 (4) |
| C16—C11—C12 | 123.0 (4) | C39—C40—N13 | 119.4 (4) |
| C16—C11—N4 | 105.7 (3) | C41—C40—N13 | 119.3 (4) |
| C12—C11—N4 | 131.3 (4) | C42—C41—C40 | 118.3 (4) |
| C11—C12—C13 | 115.9 (4) | C42—C41—H41A | 120.8 |
| C11—C12—H12A | 122.0 | C40—C41—H41A | 120.8 |
| C13—C12—H12A | 122.0 | C41—C42—C37 | 125.8 (4) |
| C12—C13—C14 | 121.4 (4) | C41—C42—N14 | 117.4 (4) |
| C12—C13—H13A | 119.3 | C37—C42—N14 | 116.9 (4) |
| N5—Ni—O1—C28 | 179.5 (3) | C12—C11—C16—C15 | 1.4 (6) |
| N3—Ni—O1—C28 | −86.7 (4) | N4—C11—C16—C15 | −178.5 (4) |
| N1—Ni—O1—C28 | 88.5 (4) | C10—N3—C16—C11 | −1.1 (5) |
| O2—Ni—O1—C28 | −1.6 (4) | Ni—N3—C16—C11 | 167.7 (3) |
| N7—Ni—O1—C28 | 134.9 (14) | C10—N3—C16—C15 | 178.6 (4) |
| N5—Ni—N1—C7 | 94.7 (3) | Ni—N3—C16—C15 | −12.5 (7) |
| N3—Ni—N1—C7 | −4.4 (5) | C14—C15—C16—C11 | −1.0 (6) |
| O1—Ni—N1—C7 | −171.4 (3) | C14—C15—C16—N3 | 179.2 (4) |
| O2—Ni—N1—C7 | −76.2 (3) | C9—N7—C17—C18 | −121.2 (4) |
| N7—Ni—N1—C7 | 12.1 (3) | C8—N7—C17—C18 | 113.8 (4) |
| N5—Ni—N1—C1 | −74.3 (4) | Ni—N7—C17—C18 | −3.2 (4) |
| N3—Ni—N1—C1 | −173.4 (4) | C24—N5—C18—N6 | −0.6 (5) |
| O1—Ni—N1—C1 | 19.6 (4) | Ni—N5—C18—N6 | 176.9 (3) |
| O2—Ni—N1—C1 | 114.8 (4) | C24—N5—C18—C17 | 179.4 (4) |
| N7—Ni—N1—C1 | −156.9 (5) | Ni—N5—C18—C17 | −3.1 (5) |
| N5—Ni—N3—C10 | −100.0 (3) | C19—N6—C18—N5 | 0.7 (5) |
| O1—Ni—N3—C10 | 165.4 (3) | C27—N6—C18—N5 | 176.5 (4) |
| N1—Ni—N3—C10 | −1.3 (6) | C19—N6—C18—C17 | −179.3 (4) |
| O2—Ni—N3—C10 | 71.4 (3) | C27—N6—C18—C17 | −3.6 (7) |
| N7—Ni—N3—C10 | −17.8 (3) | N7—C17—C18—N5 | 4.4 (6) |
| N5—Ni—N3—C16 | 91.7 (4) | N7—C17—C18—N6 | −175.5 (4) |
| O1—Ni—N3—C16 | −2.9 (4) | C18—N6—C19—C24 | −0.5 (5) |
| N1—Ni—N3—C16 | −169.6 (4) | C27—N6—C19—C24 | −176.3 (4) |
| O2—Ni—N3—C16 | −96.9 (4) | C18—N6—C19—C20 | −178.9 (5) |
| N7—Ni—N3—C16 | 173.9 (4) | C27—N6—C19—C20 | 5.2 (8) |
| N3—Ni—N5—C18 | 79.7 (3) | N6—C19—C20—C21 | 177.9 (5) |
| O1—Ni—N5—C18 | −175.9 (3) | C24—C19—C20—C21 | −0.3 (7) |
| N1—Ni—N5—C18 | −79.3 (3) | C19—C20—C21—C22 | 0.8 (7) |
| O2—Ni—N5—C18 | 10.5 (10) | C20—C21—C22—C23 | −0.6 (8) |
| N7—Ni—N5—C18 | 0.7 (3) | C21—C22—C23—C24 | −0.2 (7) |
| N3—Ni—N5—C24 | −104.1 (4) | N6—C19—C24—C23 | −179.1 (4) |
| O1—Ni—N5—C24 | 0.2 (4) | C20—C19—C24—C23 | −0.5 (7) |
| N1—Ni—N5—C24 | 96.9 (4) | N6—C19—C24—N5 | 0.1 (5) |
| O2—Ni—N5—C24 | −173.4 (7) | C20—C19—C24—N5 | 178.8 (4) |
| N7—Ni—N5—C24 | 176.9 (4) | C22—C23—C24—C19 | 0.7 (7) |
| N5—Ni—N7—C9 | 121.3 (3) | C22—C23—C24—N5 | −178.3 (4) |
| N3—Ni—N7—C9 | 27.1 (2) | C18—N5—C24—C19 | 0.3 (5) |
| O1—Ni—N7—C9 | 166.3 (14) | Ni—N5—C24—C19 | −176.0 (3) |
| N1—Ni—N7—C9 | −146.9 (3) | C18—N5—C24—C23 | 179.4 (5) |
| O2—Ni—N7—C9 | −57.1 (3) | Ni—N5—C24—C23 | 3.1 (8) |
| N5—Ni—N7—C8 | −118.4 (3) | Ni—O1—C28—N8 | −167.6 (3) |
| N3—Ni—N7—C8 | 147.3 (3) | C29—N8—C28—O1 | 1.6 (8) |
| O1—Ni—N7—C8 | −73.5 (15) | C30—N8—C28—O1 | −179.4 (4) |
| N1—Ni—N7—C8 | −26.6 (2) | O3—O3—C31—C32 | 0.00 (4) |
| O2—Ni—N7—C8 | 63.1 (2) | O3—O3—C31—C36 | 0.00 (17) |
| N5—Ni—N7—C17 | 1.5 (3) | O3—C31—C32—C33 | 175.3 (4) |
| N3—Ni—N7—C17 | −92.8 (3) | O3—C31—C32—C33 | 175.3 (4) |
| O1—Ni—N7—C17 | 46.4 (16) | C36—C31—C32—C33 | −5.2 (6) |
| N1—Ni—N7—C17 | 93.2 (3) | O3—C31—C32—N9 | −3.0 (7) |
| O2—Ni—N7—C17 | −177.0 (3) | O3—C31—C32—N9 | −3.0 (7) |
| C7—N1—C1—C6 | 1.1 (4) | C36—C31—C32—N9 | 176.5 (4) |
| Ni—N1—C1—C6 | 170.6 (3) | O5—N9—C32—C33 | −11.2 (7) |
| C7—N1—C1—C2 | −177.1 (4) | O4—N9—C32—C33 | 165.0 (5) |
| Ni—N1—C1—C2 | −7.6 (8) | O5—N9—C32—C31 | 167.2 (5) |
| N1—C1—C2—C3 | 177.8 (4) | O4—N9—C32—C31 | −16.6 (7) |
| C6—C1—C2—C3 | −0.2 (6) | C31—C32—C33—C34 | 2.7 (7) |
| C1—C2—C3—C4 | 0.4 (7) | N9—C32—C33—C34 | −178.9 (4) |
| C2—C3—C4—C5 | −0.5 (8) | C32—C33—C34—C35 | 2.1 (7) |
| C3—C4—C5—C6 | 0.2 (7) | C32—C33—C34—N10 | −176.9 (4) |
| C7—N2—C6—C1 | −0.2 (4) | O6—N10—C34—C35 | −176.9 (4) |
| C25—N2—C6—C1 | 178.2 (4) | O7—N10—C34—C35 | 2.0 (7) |
| C7—N2—C6—C5 | 177.5 (4) | O6—N10—C34—C33 | 2.1 (7) |
| C25—N2—C6—C5 | −4.1 (7) | O7—N10—C34—C33 | −179.0 (4) |
| N1—C1—C6—N2 | −0.6 (5) | C33—C34—C35—C36 | −3.8 (7) |
| C2—C1—C6—N2 | 177.8 (4) | N10—C34—C35—C36 | 175.2 (4) |
| N1—C1—C6—C5 | −178.5 (4) | C34—C35—C36—N11 | 179.7 (4) |
| C2—C1—C6—C5 | −0.1 (6) | C34—C35—C36—C31 | 0.7 (7) |
| C4—C5—C6—N2 | −177.2 (4) | O9—N11—C36—C35 | 149.3 (5) |
| C4—C5—C6—C1 | 0.1 (7) | O8—N11—C36—C35 | −29.7 (7) |
| C1—N1—C7—N2 | −1.3 (5) | O9—N11—C36—C31 | −31.7 (7) |
| Ni—N1—C7—N2 | −174.1 (3) | O8—N11—C36—C31 | 149.3 (5) |
| C1—N1—C7—C8 | 178.9 (4) | O3—C31—C36—C35 | −177.0 (4) |
| Ni—N1—C7—C8 | 6.1 (5) | O3—C31—C36—C35 | −177.0 (4) |
| C6—N2—C7—N1 | 1.0 (5) | C32—C31—C36—C35 | 3.5 (6) |
| C25—N2—C7—N1 | −177.4 (4) | O3—C31—C36—N11 | 4.1 (7) |
| C6—N2—C7—C8 | −179.3 (4) | O3—C31—C36—N11 | 4.1 (7) |
| C25—N2—C7—C8 | 2.4 (7) | C32—C31—C36—N11 | −175.4 (4) |
| C9—N7—C8—C7 | 152.8 (3) | O12—N12—C38—C39 | 27.7 (6) |
| C17—N7—C8—C7 | −82.8 (4) | O11—N12—C38—C39 | −152.9 (4) |
| Ni—N7—C8—C7 | 35.2 (4) | O12—N12—C38—C37 | −149.4 (5) |
| N1—C7—C8—N7 | −29.5 (5) | O11—N12—C38—C37 | 29.9 (6) |
| N2—C7—C8—N7 | 150.7 (4) | O10—C37—C38—C39 | −178.5 (4) |
| C8—N7—C9—C10 | −147.5 (3) | C42—C37—C38—C39 | −2.4 (6) |
| C17—N7—C9—C10 | 87.8 (4) | O10—C37—C38—N12 | −1.6 (7) |
| Ni—N7—C9—C10 | −30.6 (4) | C42—C37—C38—N12 | 174.5 (4) |
| C16—N3—C10—N4 | 0.6 (5) | N12—C38—C39—C40 | −176.3 (4) |
| Ni—N3—C10—N4 | −171.7 (3) | C37—C38—C39—C40 | 0.7 (7) |
| C16—N3—C10—C9 | 177.0 (4) | C38—C39—C40—C41 | 2.3 (6) |
| Ni—N3—C10—C9 | 4.7 (5) | C38—C39—C40—N13 | −179.8 (4) |
| C11—N4—C10—N3 | 0.2 (5) | O13—N13—C40—C39 | 2.2 (6) |
| C26—N4—C10—N3 | −180.0 (4) | O14—N13—C40—C39 | −176.2 (4) |
| C11—N4—C10—C9 | −176.2 (4) | O13—N13—C40—C41 | −179.8 (4) |
| C26—N4—C10—C9 | 3.7 (7) | O14—N13—C40—C41 | 1.8 (6) |
| N7—C9—C10—N3 | 19.0 (5) | C39—C40—C41—C42 | −3.0 (6) |
| N7—C9—C10—N4 | −165.0 (4) | N13—C40—C41—C42 | 179.0 (4) |
| C10—N4—C11—C16 | −0.9 (4) | C40—C41—C42—C37 | 1.0 (7) |
| C26—N4—C11—C16 | 179.3 (4) | C40—C41—C42—N14 | −179.6 (4) |
| C10—N4—C11—C12 | 179.2 (4) | O10—C37—C42—C41 | 177.8 (4) |
| C26—N4—C11—C12 | −0.6 (7) | C38—C37—C42—C41 | 1.6 (6) |
| C16—C11—C12—C13 | −1.0 (6) | O10—C37—C42—N14 | −1.6 (7) |
| N4—C11—C12—C13 | 178.9 (4) | C38—C37—C42—N14 | −177.8 (4) |
| C11—C12—C13—C14 | 0.3 (7) | O16—N14—C42—C41 | 128.6 (5) |
| C12—C13—C14—C15 | −0.1 (7) | O15—N14—C42—C41 | −49.3 (6) |
| C13—C14—C15—C16 | 0.4 (7) | O16—N14—C42—C37 | −51.9 (6) |
| C12—C11—C16—N3 | −178.8 (4) | O15—N14—C42—C37 | 130.2 (5) |
| N4—C11—C16—N3 | 1.3 (4) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2D···O3 | 0.86 (2) | 1.86 (2) | 2.708 (4) | 169 (6) |
| O2—H2C···O3i | 0.85 (2) | 1.95 (3) | 2.763 (4) | 160 (7) |
| Symmetry codes: (i) −x+1, −y+1, −z+1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2D···O3 | 0.86 (2) | 1.86 (2) | 2.708 (4) | 169 (6) |
| O2—H2C···O3i | 0.85 (2) | 1.95 (3) | 2.763 (4) | 160 (7) |
| Symmetry codes: (i) −x+1, −y+1, −z+1. |
We are grateful for financially support and a grant from the `Qing Lan' Talent Engineering Funds and Students' Science and Technology Innovation Funds (grant No. DXS2008–040,041) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and the `Long Yuan Qing Nian' of Gansu Province is also acknowledged
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We are interested in tris(2-benzimidazolyl)alkanes and their derivatives and we have previously reported the crystal structure of some related complexes (Wu et al., 2009; Wu et al., 2005). The benzimidazole core is of a wide interest because of its diverse biological activities, and it is a well known structure in medicinal chemistry (Horton et al. 2003). The asymmetric unit of the title compound consists of an [Ni(Mentb)(DMF)(H2O)] cation (Mentb = tris(N-methylbenzimidazol-2-ylmethyl)amine and two picrate anions (Fig.1). The NiII ion is coordinated in a slightly- distorted octahedral coordination evironment by NiN4O2 ligand set. The Mentb ligand coordinates in a tetradentate mode while a coordinated water and a dimethylformamide ligand complete the coordination. In the crystal structure, intermolecular O-H···O hydrogen bonds link the cation and one of the pictrate anions into four component centrosymmetric clusters (Fig. 2).