Acta Cryst. (2007). E63, m1568 [ doi:10.1107/S1600536807020879 ]
In the title compound, [Ni(C34H32N10)]Cl2·3CH4O, the NiII atom is in a distorted octahedral coordination environment. In the crystal structure, extensive hydrogen bonding links the ions and molecules into a three-dimensional network.
The ligand N,N,N ',N'-tetrakis (2 '-benzimidazolyl methyl) -,2-ethanediamine (EDTB) was synthesized from reported literature earlier (Hendriks et al., 1982). After, the ligand EDTB (0.58 g, 1.0 mmol) in 20 ml hot absolute methanol was added slowly to the NiCl2. 6H2O (0.24 g, 1.0 mmol) solution of 10 ml me thanol. The mixture was stirred for 1 h. After filtration, the purple solution was allowed to stand at room temperature. Purple block-shaped crystals suitable of (I) for X-ray analysis were obtained in several days in 45% yield.
The atoms of one of the methanol molecules are disordered over two sites; the atoms involved are O3, C37 with their attached H atoms. Site occupancy factors refined to 0.75 (2):0.25 (2). The H atoms bonded C atoms were placed at their idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, with Uiso(H) = 1.2–1.5Ueq(C). H atoms bonded to N atoms were placed at their indicative positions with the Uiso value being set 1.2 times of their carrier atoms, N—H = 0.86 Å. The H atoms of the hydroxyl group were refined with the constraints of O–H = 0.82 Å, and Uiso(H) =1.5Ueq(O).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
![[Figure 1]](./at2277fig1thm.gif)
| Fig. 1. View of the molecular structure of (I), showing 30% probability displacement ellipsoids. Only the major disorder component is shown. |
![[Figure 2]](./at2277fig2thm.gif)
| Fig. 2. Part of the crystal structure of (I), showing hydrogen bonds as dashed lines. |
| [Ni(C34H32N10)]Cl2·3CH4O | Z = 2 |
| Mr = 806.43 | F(000) = 844 |
| Triclinic, P1 | Dx = 1.359 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.8183 (5) Å | Cell parameters from 5644 reflections |
| b = 11.7267 (6) Å | θ = 0.00–0.00° |
| c = 16.8837 (8) Å | µ = 0.68 mm−1 |
| α = 74.312 (1)° | T = 298 K |
| β = 87.491 (1)° | Block, purple |
| γ = 73.065 (1)° | 0.30 × 0.20 × 0.20 mm |
| V = 1971.28 (16) Å3 |
| Bruker SMART CCD area-detector diffractometer | 6229 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.031 |
| graphite | θmax = 26.0°, θmin = 1.9° |
| φ and ω scans | h = −13→12 |
| 17041 measured reflections | k = −14→14 |
| 7670 independent reflections | l = −20→20 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0747P)2 + 0.9889P] where P = (Fo2 + 2Fc2)/3 |
| 7670 reflections | (Δ/σ)max < 0.001 |
| 505 parameters | Δρmax = 0.52 e Å−3 |
| 26 restraints | Δρmin = −0.50 e Å−3 |
| [Ni(C34H32N10)]Cl2·3CH4O | γ = 73.065 (1)° |
| Mr = 806.43 | V = 1971.28 (16) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 10.8183 (5) Å | Mo Kα radiation |
| b = 11.7267 (6) Å | µ = 0.68 mm−1 |
| c = 16.8837 (8) Å | T = 298 K |
| α = 74.312 (1)° | 0.30 × 0.20 × 0.20 mm |
| β = 87.491 (1)° |
| Bruker SMART CCD area-detector diffractometer | 6229 reflections with I > 2σ(I) |
| 17041 measured reflections | Rint = 0.031 |
| 7670 independent reflections | θmax = 26.0° |
| R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.145 | Δρmax = 0.52 e Å−3 |
| S = 1.05 | Δρmin = −0.50 e Å−3 |
| 7670 reflections | Absolute structure: ? |
| 505 parameters | Flack parameter: ? |
| 26 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 | Occ. (<1) | |
| Ni1 | 0.76117 (3) | 0.88541 (3) | 0.73720 (2) | 0.03295 (13) | |
| C1 | 0.6510 (3) | 0.8609 (3) | 0.58813 (18) | 0.0418 (7) | |
| H1A | 0.5788 | 0.8775 | 0.5505 | 0.050* | |
| H1B | 0.7081 | 0.7789 | 0.5909 | 0.050* | |
| C2 | 0.7239 (3) | 0.9574 (3) | 0.55753 (18) | 0.0443 (7) | |
| H2A | 0.7536 | 0.9567 | 0.5026 | 0.053* | |
| H2B | 0.6670 | 1.0393 | 0.5553 | 0.053* | |
| C3 | 0.8848 (3) | 1.0338 (3) | 0.61055 (18) | 0.0438 (7) | |
| H3A | 0.8138 | 1.1096 | 0.6006 | 0.053* | |
| H3B | 0.9443 | 1.0423 | 0.5662 | 0.053* | |
| C4 | 0.9526 (3) | 1.0095 (3) | 0.69153 (18) | 0.0381 (6) | |
| C5 | 1.0036 (3) | 0.9358 (3) | 0.82128 (19) | 0.0393 (7) | |
| C6 | 1.0163 (3) | 0.8747 (3) | 0.9047 (2) | 0.0497 (8) | |
| H6 | 0.9621 | 0.8275 | 0.9291 | 0.060* | |
| C7 | 1.1123 (4) | 0.8869 (3) | 0.9498 (2) | 0.0589 (9) | |
| H7 | 1.1221 | 0.8480 | 1.0059 | 0.071* | |
| C8 | 1.1956 (4) | 0.9562 (3) | 0.9138 (3) | 0.0608 (10) | |
| H8 | 1.2601 | 0.9612 | 0.9462 | 0.073* | |
| C9 | 1.1842 (3) | 1.0169 (3) | 0.8315 (2) | 0.0520 (8) | |
| H9 | 1.2397 | 1.0628 | 0.8074 | 0.062* | |
| C10 | 1.0864 (3) | 1.0070 (3) | 0.7856 (2) | 0.0423 (7) | |
| C11 | 0.9413 (3) | 0.8190 (3) | 0.60412 (19) | 0.0434 (7) | |
| H11A | 0.9297 | 0.8057 | 0.5510 | 0.052* | |
| H11B | 1.0239 | 0.8355 | 0.6054 | 0.052* | |
| C12 | 0.9414 (3) | 0.7065 (3) | 0.67009 (19) | 0.0404 (7) | |
| C13 | 0.9106 (3) | 0.5870 (3) | 0.7870 (2) | 0.0439 (7) | |
| C14 | 0.8774 (4) | 0.5367 (3) | 0.8664 (2) | 0.0524 (8) | |
| H14 | 0.8228 | 0.5856 | 0.8962 | 0.063* | |
| C15 | 0.9291 (4) | 0.4106 (4) | 0.8990 (3) | 0.0700 (11) | |
| H15 | 0.9104 | 0.3742 | 0.9525 | 0.084* | |
| C16 | 1.0083 (4) | 0.3365 (4) | 0.8539 (3) | 0.0775 (13) | |
| H16 | 1.0393 | 0.2517 | 0.8776 | 0.093* | |
| C17 | 1.0417 (4) | 0.3846 (4) | 0.7761 (3) | 0.0730 (12) | |
| H17 | 1.0950 | 0.3346 | 0.7465 | 0.088* | |
| C18 | 0.9927 (3) | 0.5121 (3) | 0.7428 (2) | 0.0527 (8) | |
| C19 | 0.4865 (3) | 0.9738 (3) | 0.6662 (2) | 0.0440 (7) | |
| H19A | 0.4238 | 0.9478 | 0.7042 | 0.053* | |
| H19B | 0.4474 | 1.0029 | 0.6110 | 0.053* | |
| C20 | 0.5218 (3) | 1.0769 (3) | 0.68755 (18) | 0.0386 (7) | |
| C21 | 0.5050 (3) | 1.2598 (3) | 0.70313 (19) | 0.0451 (7) | |
| C22 | 0.4686 (4) | 1.3832 (3) | 0.7052 (2) | 0.0587 (9) | |
| H22 | 0.3867 | 1.4360 | 0.6869 | 0.070* | |
| C23 | 0.5591 (4) | 1.4227 (3) | 0.7353 (3) | 0.0648 (11) | |
| H23 | 0.5379 | 1.5045 | 0.7375 | 0.078* | |
| C24 | 0.6816 (4) | 1.3445 (4) | 0.7628 (2) | 0.0622 (10) | |
| H24 | 0.7403 | 1.3752 | 0.7828 | 0.075* | |
| C25 | 0.7183 (4) | 1.2220 (3) | 0.7612 (2) | 0.0498 (8) | |
| H25 | 0.8004 | 1.1699 | 0.7799 | 0.060* | |
| C26 | 0.6285 (3) | 1.1797 (3) | 0.73060 (18) | 0.0403 (7) | |
| C27 | 0.5784 (3) | 0.7514 (3) | 0.72125 (18) | 0.0406 (7) | |
| H27A | 0.6449 | 0.6793 | 0.7140 | 0.049* | |
| H27B | 0.4950 | 0.7469 | 0.7058 | 0.049* | |
| C28 | 0.5802 (3) | 0.7576 (3) | 0.80841 (18) | 0.0380 (6) | |
| C29 | 0.5324 (3) | 0.7414 (3) | 0.9378 (2) | 0.0477 (8) | |
| C30 | 0.4836 (4) | 0.7203 (4) | 1.0160 (2) | 0.0644 (10) | |
| H30 | 0.4234 | 0.6762 | 1.0302 | 0.077* | |
| C31 | 0.5272 (5) | 0.7664 (5) | 1.0710 (2) | 0.0750 (12) | |
| H31 | 0.4957 | 0.7543 | 1.1238 | 0.090* | |
| C32 | 0.6186 (5) | 0.8317 (4) | 1.0501 (2) | 0.0728 (12) | |
| H32 | 0.6461 | 0.8619 | 1.0895 | 0.087* | |
| C33 | 0.6691 (4) | 0.8527 (4) | 0.9729 (2) | 0.0560 (9) | |
| H33 | 0.7302 | 0.8960 | 0.9594 | 0.067* | |
| C34 | 0.6239 (3) | 0.8058 (3) | 0.91627 (18) | 0.0395 (7) | |
| C35 | 0.2331 (6) | 0.5681 (6) | 0.8657 (5) | 0.122 (2) | |
| H35A | 0.2554 | 0.5382 | 0.9235 | 0.182* | |
| H35B | 0.2409 | 0.4992 | 0.8434 | 0.182* | |
| H35C | 0.1456 | 0.6209 | 0.8574 | 0.182* | |
| C36 | 0.4998 (6) | 0.6466 (4) | 0.5199 (3) | 0.1029 (18) | |
| H36A | 0.5832 | 0.6546 | 0.5022 | 0.154* | |
| H36B | 0.4745 | 0.5954 | 0.4919 | 0.154* | |
| H36C | 0.5041 | 0.6096 | 0.5782 | 0.154* | |
| Cl1 | 0.81962 (8) | 0.76367 (8) | 0.41547 (5) | 0.0523 (2) | |
| Cl2 | 0.25611 (11) | 0.79632 (15) | 0.65016 (9) | 0.0972 (4) | |
| N1 | 0.8357 (2) | 0.9273 (2) | 0.61481 (14) | 0.0388 (6) | |
| N2 | 0.6035 (2) | 0.8669 (2) | 0.67068 (15) | 0.0370 (5) | |
| N3 | 0.9191 (2) | 0.9405 (2) | 0.75989 (15) | 0.0378 (5) | |
| N4 | 1.0494 (3) | 1.0531 (2) | 0.70377 (16) | 0.0446 (6) | |
| H4 | 1.0824 | 1.1013 | 0.6671 | 0.053* | |
| N5 | 0.8790 (2) | 0.7102 (2) | 0.73796 (15) | 0.0389 (6) | |
| N6 | 1.0092 (3) | 0.5910 (3) | 0.66900 (18) | 0.0526 (7) | |
| H6A | 1.0546 | 0.5701 | 0.6293 | 0.063* | |
| N7 | 0.6534 (2) | 0.8140 (2) | 0.83407 (15) | 0.0386 (6) | |
| N8 | 0.5074 (3) | 0.7112 (3) | 0.86743 (16) | 0.0488 (7) | |
| H8A | 0.4552 | 0.6703 | 0.8626 | 0.059* | |
| N12 | 0.4403 (3) | 1.1903 (2) | 0.67747 (16) | 0.0459 (6) | |
| H12 | 0.3618 | 1.2153 | 0.6584 | 0.055* | |
| N13 | 0.6354 (2) | 1.0632 (2) | 0.71968 (15) | 0.0398 (6) | |
| O1 | 0.3132 (4) | 0.6324 (5) | 0.8274 (3) | 0.1190 (14) | |
| H1 | 0.2816 | 0.6754 | 0.7820 | 0.178* | |
| O2 | 0.4147 (6) | 0.7566 (4) | 0.5025 (3) | 0.154 (2) | |
| H2 | 0.3433 | 0.7497 | 0.5171 | 0.231* | |
| O3 | 0.1666 (6) | 0.5150 (6) | 0.5485 (3) | 0.100 (3) | 0.752 (18) |
| H3 | 0.1713 | 0.4426 | 0.5524 | 0.150* | 0.752 (18) |
| C37 | 0.1726 (9) | 0.5770 (9) | 0.4660 (4) | 0.101 (3) | 0.752 (18) |
| H37A | 0.1762 | 0.6592 | 0.4620 | 0.152* | 0.752 (18) |
| H37B | 0.0972 | 0.5814 | 0.4361 | 0.152* | 0.752 (18) |
| H37C | 0.2486 | 0.5331 | 0.4432 | 0.152* | 0.752 (18) |
| C37' | 0.143 (10) | 0.581 (10) | 0.460 (4) | 0.37 (6) | 0.248 (18) |
| H37D | 0.0541 | 0.6280 | 0.4461 | 0.558* | 0.248 (18) |
| H37E | 0.1533 | 0.4957 | 0.4632 | 0.558* | 0.248 (18) |
| H37F | 0.1965 | 0.6126 | 0.4176 | 0.558* | 0.248 (18) |
| O3' | 0.178 (3) | 0.591 (4) | 0.5330 (19) | 0.155 (11) | 0.248 (18) |
| H3' | 0.2517 | 0.5977 | 0.5310 | 0.232* | 0.248 (18) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.0340 (2) | 0.0360 (2) | 0.0319 (2) | −0.01547 (16) | 0.00156 (14) | −0.00855 (15) |
| C1 | 0.0439 (18) | 0.0517 (18) | 0.0352 (15) | −0.0184 (15) | −0.0050 (13) | −0.0149 (13) |
| C2 | 0.0507 (19) | 0.0497 (18) | 0.0316 (15) | −0.0177 (15) | −0.0015 (13) | −0.0055 (13) |
| C3 | 0.0516 (19) | 0.0449 (17) | 0.0365 (16) | −0.0236 (15) | 0.0040 (13) | −0.0033 (13) |
| C4 | 0.0415 (17) | 0.0378 (15) | 0.0390 (15) | −0.0174 (13) | 0.0052 (13) | −0.0111 (12) |
| C5 | 0.0374 (16) | 0.0394 (16) | 0.0434 (16) | −0.0110 (13) | 0.0013 (13) | −0.0150 (13) |
| C6 | 0.053 (2) | 0.0480 (18) | 0.0473 (18) | −0.0194 (16) | −0.0051 (15) | −0.0050 (15) |
| C7 | 0.067 (2) | 0.060 (2) | 0.051 (2) | −0.0205 (19) | −0.0133 (17) | −0.0106 (17) |
| C8 | 0.055 (2) | 0.056 (2) | 0.075 (3) | −0.0177 (18) | −0.0210 (19) | −0.0204 (19) |
| C9 | 0.048 (2) | 0.052 (2) | 0.066 (2) | −0.0231 (16) | 0.0001 (16) | −0.0220 (17) |
| C10 | 0.0417 (18) | 0.0412 (17) | 0.0496 (18) | −0.0157 (14) | 0.0017 (14) | −0.0174 (14) |
| C11 | 0.0413 (18) | 0.0512 (18) | 0.0395 (16) | −0.0166 (15) | 0.0069 (13) | −0.0126 (14) |
| C12 | 0.0366 (16) | 0.0449 (17) | 0.0421 (16) | −0.0121 (13) | −0.0003 (13) | −0.0150 (13) |
| C13 | 0.0414 (18) | 0.0388 (16) | 0.0492 (18) | −0.0098 (14) | −0.0053 (14) | −0.0090 (14) |
| C14 | 0.058 (2) | 0.0445 (18) | 0.0509 (19) | −0.0137 (16) | 0.0015 (16) | −0.0069 (15) |
| C15 | 0.085 (3) | 0.050 (2) | 0.063 (2) | −0.016 (2) | 0.002 (2) | −0.0002 (18) |
| C16 | 0.078 (3) | 0.039 (2) | 0.094 (3) | −0.001 (2) | −0.001 (2) | 0.001 (2) |
| C17 | 0.074 (3) | 0.045 (2) | 0.090 (3) | −0.0027 (19) | 0.007 (2) | −0.019 (2) |
| C18 | 0.048 (2) | 0.0436 (18) | 0.063 (2) | −0.0085 (15) | 0.0007 (16) | −0.0139 (16) |
| C19 | 0.0342 (16) | 0.0456 (17) | 0.0534 (18) | −0.0120 (14) | −0.0042 (14) | −0.0139 (14) |
| C20 | 0.0401 (17) | 0.0357 (15) | 0.0386 (15) | −0.0098 (13) | −0.0001 (13) | −0.0090 (12) |
| C21 | 0.056 (2) | 0.0414 (17) | 0.0386 (16) | −0.0147 (15) | 0.0066 (14) | −0.0127 (13) |
| C22 | 0.069 (2) | 0.0436 (19) | 0.059 (2) | −0.0122 (18) | 0.0079 (18) | −0.0116 (16) |
| C23 | 0.087 (3) | 0.0391 (19) | 0.077 (3) | −0.027 (2) | 0.019 (2) | −0.0237 (18) |
| C24 | 0.077 (3) | 0.060 (2) | 0.069 (2) | −0.040 (2) | 0.016 (2) | −0.0294 (19) |
| C25 | 0.053 (2) | 0.0531 (19) | 0.054 (2) | −0.0251 (16) | 0.0080 (16) | −0.0231 (16) |
| C26 | 0.0471 (18) | 0.0413 (16) | 0.0365 (15) | −0.0190 (14) | 0.0071 (13) | −0.0110 (13) |
| C27 | 0.0408 (17) | 0.0426 (17) | 0.0451 (17) | −0.0209 (14) | 0.0008 (13) | −0.0132 (13) |
| C28 | 0.0386 (16) | 0.0396 (16) | 0.0390 (15) | −0.0176 (13) | 0.0011 (12) | −0.0087 (12) |
| C29 | 0.0470 (19) | 0.055 (2) | 0.0418 (17) | −0.0215 (16) | 0.0020 (14) | −0.0073 (14) |
| C30 | 0.069 (3) | 0.085 (3) | 0.048 (2) | −0.042 (2) | 0.0133 (18) | −0.0127 (19) |
| C31 | 0.085 (3) | 0.110 (4) | 0.041 (2) | −0.048 (3) | 0.0204 (19) | −0.020 (2) |
| C32 | 0.091 (3) | 0.101 (3) | 0.046 (2) | −0.046 (3) | 0.014 (2) | −0.033 (2) |
| C33 | 0.067 (2) | 0.068 (2) | 0.0444 (18) | −0.033 (2) | 0.0078 (16) | −0.0209 (17) |
| C34 | 0.0386 (16) | 0.0450 (17) | 0.0369 (15) | −0.0174 (14) | 0.0042 (12) | −0.0089 (13) |
| C35 | 0.095 (4) | 0.121 (5) | 0.173 (7) | −0.059 (4) | 0.020 (4) | −0.051 (4) |
| C36 | 0.152 (6) | 0.059 (3) | 0.088 (4) | −0.021 (3) | 0.011 (3) | −0.015 (3) |
| Cl1 | 0.0505 (5) | 0.0553 (5) | 0.0541 (5) | −0.0238 (4) | 0.0026 (4) | −0.0107 (4) |
| Cl2 | 0.0509 (6) | 0.1369 (12) | 0.1111 (10) | −0.0283 (7) | 0.0003 (6) | −0.0437 (9) |
| N1 | 0.0427 (14) | 0.0419 (14) | 0.0340 (12) | −0.0185 (12) | 0.0018 (10) | −0.0073 (10) |
| N2 | 0.0406 (14) | 0.0362 (13) | 0.0367 (13) | −0.0140 (11) | −0.0014 (10) | −0.0104 (10) |
| N3 | 0.0361 (13) | 0.0414 (13) | 0.0370 (13) | −0.0161 (11) | −0.0012 (10) | −0.0066 (10) |
| N4 | 0.0454 (15) | 0.0476 (15) | 0.0484 (15) | −0.0258 (13) | 0.0095 (12) | −0.0135 (12) |
| N5 | 0.0383 (14) | 0.0405 (14) | 0.0377 (13) | −0.0118 (11) | 0.0009 (10) | −0.0097 (11) |
| N6 | 0.0523 (17) | 0.0521 (17) | 0.0561 (17) | −0.0130 (14) | 0.0134 (13) | −0.0233 (14) |
| N7 | 0.0419 (14) | 0.0426 (14) | 0.0370 (13) | −0.0196 (12) | 0.0048 (11) | −0.0127 (11) |
| N8 | 0.0504 (16) | 0.0591 (17) | 0.0459 (15) | −0.0334 (14) | 0.0044 (12) | −0.0106 (13) |
| N12 | 0.0435 (15) | 0.0448 (15) | 0.0465 (15) | −0.0085 (12) | −0.0026 (12) | −0.0116 (12) |
| N13 | 0.0432 (15) | 0.0384 (13) | 0.0419 (14) | −0.0158 (11) | 0.0016 (11) | −0.0136 (11) |
| O1 | 0.098 (3) | 0.168 (4) | 0.120 (3) | −0.091 (3) | −0.016 (2) | −0.026 (3) |
| O2 | 0.187 (5) | 0.101 (3) | 0.107 (3) | 0.023 (3) | 0.025 (3) | 0.009 (2) |
| O3 | 0.135 (4) | 0.065 (3) | 0.105 (4) | −0.028 (3) | 0.051 (3) | −0.039 (3) |
| C37 | 0.082 (5) | 0.094 (5) | 0.094 (5) | −0.002 (4) | 0.015 (4) | 0.003 (4) |
| C37' | 0.37 (6) | 0.37 (6) | 0.37 (6) | −0.11 (2) | 0.009 (11) | −0.098 (19) |
| O3' | 0.158 (13) | 0.151 (15) | 0.163 (14) | −0.052 (9) | 0.017 (9) | −0.049 (10) |
| Ni1—N5 | 2.076 (2) | C21—N12 | 1.375 (4) |
| Ni1—N3 | 2.078 (2) | C21—C22 | 1.394 (5) |
| Ni1—N13 | 2.082 (2) | C21—C26 | 1.403 (5) |
| Ni1—N7 | 2.097 (2) | C22—C23 | 1.367 (6) |
| Ni1—N1 | 2.167 (2) | C22—H22 | 0.9300 |
| Ni1—N2 | 2.175 (2) | C23—C24 | 1.389 (6) |
| C1—N2 | 1.476 (4) | C23—H23 | 0.9300 |
| C1—C2 | 1.528 (4) | C24—C25 | 1.382 (5) |
| C1—H1A | 0.9700 | C24—H24 | 0.9300 |
| C1—H1B | 0.9700 | C25—C26 | 1.385 (4) |
| C2—N1 | 1.481 (4) | C25—H25 | 0.9300 |
| C2—H2A | 0.9700 | C26—N13 | 1.408 (4) |
| C2—H2B | 0.9700 | C27—N2 | 1.485 (4) |
| C3—N1 | 1.476 (4) | C27—C28 | 1.494 (4) |
| C3—C4 | 1.498 (4) | C27—H27A | 0.9700 |
| C3—H3A | 0.9700 | C27—H27B | 0.9700 |
| C3—H3B | 0.9700 | C28—N7 | 1.320 (4) |
| C4—N3 | 1.321 (4) | C28—N8 | 1.340 (4) |
| C4—N4 | 1.339 (4) | C29—C30 | 1.386 (5) |
| C5—C6 | 1.389 (4) | C29—N8 | 1.386 (4) |
| C5—N3 | 1.391 (4) | C29—C34 | 1.392 (4) |
| C5—C10 | 1.406 (4) | C30—C31 | 1.354 (6) |
| C6—C7 | 1.377 (5) | C30—H30 | 0.9300 |
| C6—H6 | 0.9300 | C31—C32 | 1.397 (6) |
| C7—C8 | 1.397 (5) | C31—H31 | 0.9300 |
| C7—H7 | 0.9300 | C32—C33 | 1.378 (5) |
| C8—C9 | 1.372 (5) | C32—H32 | 0.9300 |
| C8—H8 | 0.9300 | C33—C34 | 1.393 (5) |
| C9—C10 | 1.387 (5) | C33—H33 | 0.9300 |
| C9—H9 | 0.9300 | C34—N7 | 1.394 (4) |
| C10—N4 | 1.371 (4) | C35—O1 | 1.344 (6) |
| C11—C12 | 1.478 (4) | C35—H35A | 0.9600 |
| C11—N1 | 1.488 (4) | C35—H35B | 0.9600 |
| C11—H11A | 0.9700 | C35—H35C | 0.9600 |
| C11—H11B | 0.9700 | C36—O2 | 1.313 (6) |
| C12—N5 | 1.309 (4) | C36—H36A | 0.9600 |
| C12—N6 | 1.345 (4) | C36—H36B | 0.9600 |
| C13—C14 | 1.388 (5) | C36—H36C | 0.9600 |
| C13—C18 | 1.400 (5) | N4—H4 | 0.8600 |
| C13—N5 | 1.407 (4) | N6—H6A | 0.8600 |
| C14—C15 | 1.381 (5) | N8—H8A | 0.8600 |
| C14—H14 | 0.9300 | N12—H12 | 0.8600 |
| C15—C16 | 1.390 (6) | O1—H1 | 0.8200 |
| C15—H15 | 0.9300 | O2—H2 | 0.8200 |
| C16—C17 | 1.360 (6) | O3—C37 | 1.395 (7) |
| C16—H16 | 0.9300 | O3—H3 | 0.8200 |
| C17—C18 | 1.393 (5) | C37—H37A | 0.9600 |
| C17—H17 | 0.9300 | C37—H37B | 0.9600 |
| C18—N6 | 1.376 (4) | C37—H37C | 0.9600 |
| C19—N2 | 1.488 (4) | C37'—O3' | 1.358 (9) |
| C19—C20 | 1.502 (4) | C37'—H37D | 0.9600 |
| C19—H19A | 0.9700 | C37'—H37E | 0.9600 |
| C19—H19B | 0.9700 | C37'—H37F | 0.9600 |
| C20—N13 | 1.314 (4) | O3'—H3' | 0.8200 |
| C20—N12 | 1.335 (4) | ||
| N5—Ni1—N3 | 91.55 (10) | C22—C23—C24 | 122.0 (3) |
| N5—Ni1—N13 | 171.99 (10) | C22—C23—H23 | 119.0 |
| N3—Ni1—N13 | 92.50 (10) | C24—C23—H23 | 119.0 |
| N5—Ni1—N7 | 92.35 (10) | C25—C24—C23 | 121.6 (4) |
| N3—Ni1—N7 | 120.95 (10) | C25—C24—H24 | 119.2 |
| N13—Ni1—N7 | 91.49 (10) | C23—C24—H24 | 119.2 |
| N5—Ni1—N1 | 80.72 (9) | C24—C25—C26 | 117.5 (4) |
| N3—Ni1—N1 | 79.15 (9) | C24—C25—H25 | 121.2 |
| N13—Ni1—N1 | 93.27 (9) | C26—C25—H25 | 121.2 |
| N7—Ni1—N1 | 159.13 (10) | C25—C26—C21 | 120.3 (3) |
| N5—Ni1—N2 | 93.07 (9) | C25—C26—N13 | 131.7 (3) |
| N3—Ni1—N2 | 159.90 (9) | C21—C26—N13 | 108.0 (3) |
| N13—Ni1—N2 | 80.83 (9) | N2—C27—C28 | 105.7 (2) |
| N7—Ni1—N2 | 78.41 (9) | N2—C27—H27A | 110.6 |
| N1—Ni1—N2 | 82.31 (9) | C28—C27—H27A | 110.6 |
| N2—C1—C2 | 108.7 (2) | N2—C27—H27B | 110.6 |
| N2—C1—H1A | 110.0 | C28—C27—H27B | 110.6 |
| C2—C1—H1A | 110.0 | H27A—C27—H27B | 108.7 |
| N2—C1—H1B | 110.0 | N7—C28—N8 | 113.1 (3) |
| C2—C1—H1B | 110.0 | N7—C28—C27 | 122.0 (3) |
| H1A—C1—H1B | 108.3 | N8—C28—C27 | 124.9 (3) |
| N1—C2—C1 | 108.6 (2) | C30—C29—N8 | 132.6 (3) |
| N1—C2—H2A | 110.0 | C30—C29—C34 | 121.8 (3) |
| C1—C2—H2A | 110.0 | N8—C29—C34 | 105.6 (3) |
| N1—C2—H2B | 110.0 | C31—C30—C29 | 117.4 (4) |
| C1—C2—H2B | 110.0 | C31—C30—H30 | 121.3 |
| H2A—C2—H2B | 108.3 | C29—C30—H30 | 121.3 |
| N1—C3—C4 | 107.2 (2) | C30—C31—C32 | 121.4 (3) |
| N1—C3—H3A | 110.3 | C30—C31—H31 | 119.3 |
| C4—C3—H3A | 110.3 | C32—C31—H31 | 119.3 |
| N1—C3—H3B | 110.3 | C33—C32—C31 | 122.2 (4) |
| C4—C3—H3B | 110.3 | C33—C32—H32 | 118.9 |
| H3A—C3—H3B | 108.5 | C31—C32—H32 | 118.9 |
| N3—C4—N4 | 113.0 (3) | C32—C33—C34 | 116.4 (3) |
| N3—C4—C3 | 121.3 (3) | C32—C33—H33 | 121.8 |
| N4—C4—C3 | 125.7 (3) | C34—C33—H33 | 121.8 |
| C6—C5—N3 | 131.2 (3) | C29—C34—C33 | 120.8 (3) |
| C6—C5—C10 | 120.4 (3) | C29—C34—N7 | 109.1 (3) |
| N3—C5—C10 | 108.3 (3) | C33—C34—N7 | 130.1 (3) |
| C7—C6—C5 | 117.3 (3) | O1—C35—H35A | 109.5 |
| C7—C6—H6 | 121.3 | O1—C35—H35B | 109.5 |
| C5—C6—H6 | 121.3 | H35A—C35—H35B | 109.5 |
| C6—C7—C8 | 122.0 (3) | O1—C35—H35C | 109.5 |
| C6—C7—H7 | 119.0 | H35A—C35—H35C | 109.5 |
| C8—C7—H7 | 119.0 | H35B—C35—H35C | 109.5 |
| C9—C8—C7 | 121.3 (3) | O2—C36—H36A | 109.5 |
| C9—C8—H8 | 119.4 | O2—C36—H36B | 109.5 |
| C7—C8—H8 | 119.4 | H36A—C36—H36B | 109.5 |
| C8—C9—C10 | 117.3 (3) | O2—C36—H36C | 109.5 |
| C8—C9—H9 | 121.4 | H36A—C36—H36C | 109.5 |
| C10—C9—H9 | 121.4 | H36B—C36—H36C | 109.5 |
| N4—C10—C9 | 132.5 (3) | C3—N1—C2 | 113.5 (2) |
| N4—C10—C5 | 105.8 (3) | C3—N1—C11 | 111.1 (2) |
| C9—C10—C5 | 121.7 (3) | C2—N1—C11 | 111.7 (2) |
| C12—C11—N1 | 110.6 (2) | C3—N1—Ni1 | 104.52 (17) |
| C12—C11—H11A | 109.5 | C2—N1—Ni1 | 105.47 (18) |
| N1—C11—H11A | 109.5 | C11—N1—Ni1 | 110.16 (17) |
| C12—C11—H11B | 109.5 | C1—N2—C27 | 114.3 (2) |
| N1—C11—H11B | 109.5 | C1—N2—C19 | 111.8 (2) |
| H11A—C11—H11B | 108.1 | C27—N2—C19 | 109.8 (2) |
| N5—C12—N6 | 112.8 (3) | C1—N2—Ni1 | 106.06 (18) |
| N5—C12—C11 | 122.9 (3) | C27—N2—Ni1 | 104.33 (17) |
| N6—C12—C11 | 124.3 (3) | C19—N2—Ni1 | 110.27 (17) |
| C14—C13—C18 | 120.8 (3) | C4—N3—C5 | 105.3 (2) |
| C14—C13—N5 | 131.1 (3) | C4—N3—Ni1 | 110.72 (19) |
| C18—C13—N5 | 108.0 (3) | C5—N3—Ni1 | 143.9 (2) |
| C15—C14—C13 | 116.9 (3) | C4—N4—C10 | 107.4 (2) |
| C15—C14—H14 | 121.5 | C4—N4—H4 | 126.3 |
| C13—C14—H14 | 121.5 | C10—N4—H4 | 126.3 |
| C14—C15—C16 | 121.8 (4) | C12—N5—C13 | 105.7 (3) |
| C14—C15—H15 | 119.1 | C12—N5—Ni1 | 113.6 (2) |
| C16—C15—H15 | 119.1 | C13—N5—Ni1 | 140.5 (2) |
| C17—C16—C15 | 121.9 (4) | C12—N6—C18 | 107.6 (3) |
| C17—C16—H16 | 119.1 | C12—N6—H6A | 126.2 |
| C15—C16—H16 | 119.1 | C18—N6—H6A | 126.2 |
| C16—C17—C18 | 117.2 (4) | C28—N7—C34 | 105.1 (2) |
| C16—C17—H17 | 121.4 | C28—N7—Ni1 | 110.24 (19) |
| C18—C17—H17 | 121.4 | C34—N7—Ni1 | 144.6 (2) |
| N6—C18—C17 | 132.8 (4) | C28—N8—C29 | 107.1 (3) |
| N6—C18—C13 | 105.8 (3) | C28—N8—H8A | 126.4 |
| C17—C18—C13 | 121.3 (4) | C29—N8—H8A | 126.4 |
| N2—C19—C20 | 110.3 (2) | C20—N12—C21 | 107.5 (3) |
| N2—C19—H19A | 109.6 | C20—N12—H12 | 126.3 |
| C20—C19—H19A | 109.6 | C21—N12—H12 | 126.3 |
| N2—C19—H19B | 109.6 | C20—N13—C26 | 105.1 (3) |
| C20—C19—H19B | 109.6 | C20—N13—Ni1 | 113.40 (19) |
| H19A—C19—H19B | 108.1 | C26—N13—Ni1 | 141.5 (2) |
| N13—C20—N12 | 113.5 (3) | C35—O1—H1 | 109.5 |
| N13—C20—C19 | 123.1 (3) | C36—O2—H2 | 109.5 |
| N12—C20—C19 | 123.4 (3) | O3'—C37'—H37D | 109.5 |
| N12—C21—C22 | 132.3 (3) | O3'—C37'—H37E | 109.5 |
| N12—C21—C26 | 105.9 (3) | H37D—C37'—H37E | 109.5 |
| C22—C21—C26 | 121.8 (3) | O3'—C37'—H37F | 109.5 |
| C23—C22—C21 | 116.8 (4) | H37D—C37'—H37F | 109.5 |
| C23—C22—H22 | 121.6 | H37E—C37'—H37F | 109.5 |
| C21—C22—H22 | 121.6 | C37'—O3'—H3' | 109.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···Cl1i | 0.82 | 2.30 | 3.117 (7) | 171 |
| N4—H4···Cl1ii | 0.86 | 2.29 | 3.140 (3) | 172 |
| N6—H6A···O3iii | 0.86 | 1.90 | 2.761 (5) | 175 |
| N12—H12···Cl1iv | 0.86 | 2.29 | 3.116 (3) | 162 |
| C2—H2B···O2iv | 0.97 | 2.25 | 3.145 (5) | 154 |
| C11—H11B···Cl2iii | 0.97 | 2.53 | 3.445 (3) | 157 |
| O1—H1···Cl2 | 0.82 | 2.27 | 3.065 (4) | 163 |
| O2—H2···Cl2 | 0.82 | 2.53 | 3.027 (5) | 120 |
| N8—H8A···O1 | 0.86 | 1.88 | 2.705 (4) | 161 |
| C27—H27B···Cl2 | 0.97 | 2.64 | 3.582 (3) | 165 |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+2, −z+1. |
| Ni1—N5 | 2.076 (2) | Ni1—N7 | 2.097 (2) |
| Ni1—N3 | 2.078 (2) | Ni1—N1 | 2.167 (2) |
| Ni1—N13 | 2.082 (2) | Ni1—N2 | 2.175 (2) |
| N5—Ni1—N3 | 91.55 (10) | N13—Ni1—N1 | 93.27 (9) |
| N5—Ni1—N13 | 171.99 (10) | N7—Ni1—N1 | 159.13 (10) |
| N3—Ni1—N13 | 92.50 (10) | N5—Ni1—N2 | 93.07 (9) |
| N5—Ni1—N7 | 92.35 (10) | N3—Ni1—N2 | 159.90 (9) |
| N3—Ni1—N7 | 120.95 (10) | N13—Ni1—N2 | 80.83 (9) |
| N13—Ni1—N7 | 91.49 (10) | N7—Ni1—N2 | 78.41 (9) |
| N5—Ni1—N1 | 80.72 (9) | N1—Ni1—N2 | 82.31 (9) |
| N3—Ni1—N1 | 79.15 (9) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···Cl1i | 0.82 | 2.30 | 3.117 (7) | 171 |
| N4—H4···Cl1ii | 0.86 | 2.29 | 3.140 (3) | 172 |
| N6—H6A···O3iii | 0.86 | 1.90 | 2.761 (5) | 175 |
| N12—H12···Cl1iv | 0.86 | 2.29 | 3.116 (3) | 162 |
| C2—H2B···O2iv | 0.97 | 2.25 | 3.145 (5) | 154 |
| C11—H11B···Cl2iii | 0.97 | 2.53 | 3.445 (3) | 157 |
| O1—H1···Cl2 | 0.82 | 2.27 | 3.065 (4) | 163 |
| O2—H2···Cl2 | 0.82 | 2.53 | 3.027 (5) | 120 |
| N8—H8A···O1 | 0.86 | 1.88 | 2.705 (4) | 161 |
| C27—H27B···Cl2 | 0.97 | 2.64 | 3.582 (3) | 165 |
| Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+2, −z+1; (iii) x+1, y, z; (iv) −x+1, −y+2, −z+1. |
Bruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS, Inc., Madison, Wisconsin, USA.
Chen, Z.-F., Liao, Z.-R., Li, D.-F., Li, W.-K. & Meng, X.-G. (2004). J. Inorg. Biochem. 98, 1315–1318.
Hendriks, H. M. J., van Birker, P. J. M. W. L. & Rijn, J. (1982). J. Am. Chem. Soc. pp. 3607–3617.
Liao, Z.-R., Zheng, X.-F., Luo, B.-S., Shen, L.-R., Li, D.-F., Liu, H.-L. & Zhao, W. (2001). Polyhedron, 20, 2813–2821.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Recently, study in the ligands containing-polybenzimidazoles and their metal coordination compounds has been widely carried on (Chen et al., 2004; Liao et al., 2001). As the continuing work of our workgroup, we report the crystallography structure of the title compound, [Ni(EDTB)]2Cl-.3CH3OH, (I); {EDTB = N,N,N',N'-tetrakis(2'-benzimidazolyl methyl)-1,2-ethanediamine}.
In the title molecular structure (I), NiII is coordinated by four four benzimidazole nitrogen atoms, two amino N atoms of EDTB, forming a distorted octahedron coordination geometry (Table 1 and Fig. 1).
In the supramolecular structure, there are a number of N(or O)–H···Cl, N–H···O and O–H···N hydrogen bonding interactions which link the molecules into a three-dimensional framwork (Table 2 and Fig.2.).