Acta Cryst. (2007). E63, m3063-m3064 [ doi:10.1107/S1600536807058370 ]
The title complex, [Ni(C2H1N9)(C10H8N2)2]·6H2O, was prepared under hydrothermal reaction conditions. The asymmetric unit contains the nickel complex and six solvent water molecules. The NiII ion is coordinated in a distorted octahedral geometry defined by four N atoms from two 2,2'-bipyridine ligands and two N atoms from the 5,5'-iminobis(tetrazolate) (BTA2-) anions. In the crystal structure, an extensive range of O-H
N and O-HO hydrogen bonds links the complex and the water molecules into a three-dimensional network.
A mixture of Ni(Cl)2·6H2O (0.024 g, 0.1 mmol), bistetrazolylimine (0.031 g, 0.02 mmol) and water (20 ml) was heated in a 25 ml Teflon-lined autoclave at 433 K for 3 d, followed by slow cooling to room temperature. The resulting mixture was filtered, washed with 95% methanol and red crystals were collected and dried in air. Elemental analysis, calcd (%) for C22H29N13Ni1O6: C 41.90, H 4.60, N 28.89; found(%): C 41.66, H 4.93, N 28.71.
All hydrogen atoms were located in difference Fourier maps and freely refined with isotropic displacement parameters.
Data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXTL (Bruker, 2005).
![[Figure 1]](./sj2411fig1thm.gif)
| Fig. 1. The asymmetric unit of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. |
![[Figure 2]](./sj2411fig2thm.gif)
| Fig. 2. The packing of the complex, showing a three-dimensional network connected by O—H···N and O—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted. |
| [Ni(C2H1N9)(C10H8N2)2]·6H2O | F000 = 1312.0 |
| Mr = 630.27 | Dx = 1.480 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 5453 reflections |
| a = 13.3435 (3) Å | θ = 1.0–27.5º |
| b = 13.3741 (3) Å | µ = 0.75 mm−1 |
| c = 15.9408 (3) Å | T = 296 (2) K |
| β = 96.166 (1)º | Block, red |
| V = 2828.29 (10) Å3 | 0.25 × 0.25 × 0.13 mm |
| Z = 4 |
| Bruker SMART APEX CCD area-detector diffractometer | 6503 independent reflections |
| Radiation source: fine-focus sealed tube | 5453 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.024 |
| T = 296(2) K | θmax = 27.5º |
| φ and ω scans | θmin = 1.9º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→16 |
| Tmin = 0.830, Tmax = 0.907 | k = −16→17 |
| 6514 measured reflections | l = −20→20 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | All H-atom parameters refined |
| R[F2 > 2σ(F2)] = 0.028 | w = 1/[σ2(Fo2) + (0.0359P)2 + 0.8759P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.075 | (Δ/σ)max = 0.033 |
| S = 1.03 | Δρmax = 0.32 e Å−3 |
| 6503 reflections | Δρmin = −0.30 e Å−3 |
| 496 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0018 |
| Secondary atom site location: difference Fourier map |
| [Ni(C2H1N9)(C10H8N2)2]·6H2O | V = 2828.29 (10) Å3 |
| Mr = 630.27 | Z = 4 |
| Monoclinic, P21/n | Mo Kα |
| a = 13.3435 (3) Å | µ = 0.75 mm−1 |
| b = 13.3741 (3) Å | T = 296 (2) K |
| c = 15.9408 (3) Å | 0.25 × 0.25 × 0.13 mm |
| β = 96.166 (1)º |
| Bruker SMART APEX CCD area-detector diffractometer | 6503 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5453 reflections with I > 2σ(I) |
| Tmin = 0.830, Tmax = 0.907 | Rint = 0.024 |
| 6514 measured reflections |
| R[F2 > 2σ(F2)] = 0.028 | 496 parameters |
| wR(F2) = 0.075 | All H-atom parameters refined |
| S = 1.03 | Δρmax = 0.32 e Å−3 |
| 6503 reflections | Δρmin = −0.30 e Å−3 |
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 > 2sigma(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 | ||
| Ni1 | 0.721520 (13) | 0.120775 (13) | 0.874767 (11) | 0.02942 (7) | |
| C1 | 0.59648 (11) | 0.30488 (11) | 0.90861 (9) | 0.0327 (3) | |
| N4 | 0.50270 (10) | 0.33969 (10) | 0.90652 (9) | 0.0394 (3) | |
| N1 | 0.60038 (9) | 0.21948 (9) | 0.86584 (8) | 0.0331 (3) | |
| N5 | 0.67785 (10) | 0.35362 (11) | 0.94830 (10) | 0.0422 (3) | |
| N6 | 0.80563 (9) | 0.24861 (9) | 0.90063 (8) | 0.0331 (3) | |
| N3 | 0.44671 (10) | 0.27279 (11) | 0.85844 (9) | 0.0422 (3) | |
| N7 | 0.90583 (10) | 0.26122 (11) | 0.89697 (9) | 0.0426 (3) | |
| N2 | 0.50342 (9) | 0.20166 (10) | 0.83404 (8) | 0.0390 (3) | |
| N8 | 0.93118 (11) | 0.34970 (12) | 0.92545 (11) | 0.0530 (4) | |
| N9 | 0.85003 (11) | 0.39895 (11) | 0.94812 (10) | 0.0487 (4) | |
| C2 | 0.77503 (11) | 0.33450 (11) | 0.93208 (9) | 0.0337 (3) | |
| N10 | 0.74488 (10) | 0.12590 (9) | 0.74820 (8) | 0.0385 (3) | |
| N11 | 0.84590 (9) | 0.02420 (9) | 0.87217 (8) | 0.0349 (3) | |
| C8 | 0.87850 (11) | 0.01380 (12) | 0.79555 (10) | 0.0376 (3) | |
| C7 | 0.82656 (12) | 0.07651 (12) | 0.72765 (10) | 0.0385 (3) | |
| N12 | 0.70809 (9) | 0.09258 (9) | 1.00247 (7) | 0.0332 (3) | |
| C11 | 0.96054 (14) | −0.10370 (14) | 0.92476 (14) | 0.0516 (4) | |
| C3 | 0.69266 (16) | 0.18066 (15) | 0.68884 (11) | 0.0541 (5) | |
| C12 | 0.88732 (13) | −0.03314 (13) | 0.93510 (11) | 0.0429 (4) | |
| C9 | 0.95315 (13) | −0.05460 (15) | 0.78158 (13) | 0.0519 (5) | |
| C6 | 0.85729 (16) | 0.08335 (16) | 0.64746 (12) | 0.0543 (5) | |
| C10 | 0.99352 (14) | −0.11430 (15) | 0.84671 (14) | 0.0572 (5) | |
| C4 | 0.71786 (19) | 0.18806 (17) | 0.60757 (12) | 0.0652 (6) | |
| C5 | 0.8023 (2) | 0.13933 (17) | 0.58733 (12) | 0.0657 (6) | |
| N13 | 0.62922 (10) | −0.00624 (9) | 0.86724 (8) | 0.0361 (3) | |
| C14 | 0.74236 (14) | 0.11884 (14) | 1.15098 (11) | 0.0474 (4) | |
| C18 | 0.61425 (11) | −0.04722 (11) | 0.94200 (10) | 0.0370 (3) | |
| C13 | 0.74823 (13) | 0.14660 (13) | 1.06856 (10) | 0.0399 (3) | |
| C17 | 0.65970 (11) | 0.00724 (11) | 1.01771 (10) | 0.0354 (3) | |
| C22 | 0.58868 (14) | −0.05149 (14) | 0.79670 (12) | 0.0487 (4) | |
| C16 | 0.65403 (15) | −0.02582 (15) | 1.09968 (12) | 0.0514 (4) | |
| C15 | 0.69570 (16) | 0.03107 (16) | 1.16643 (12) | 0.0551 (5) | |
| C19 | 0.55832 (15) | −0.13399 (13) | 0.94686 (13) | 0.0504 (4) | |
| C20 | 0.51727 (16) | −0.17936 (15) | 0.87395 (14) | 0.0582 (5) | |
| C21 | 0.53251 (16) | −0.13798 (15) | 0.79769 (14) | 0.0587 (5) | |
| O1 | 0.88828 (12) | 0.53330 (12) | 0.08779 (10) | 0.0591 (4) | |
| O2 | 0.62370 (14) | 0.49551 (13) | 0.06176 (10) | 0.0710 (5) | |
| O3 | 0.86502 (14) | 0.35155 (15) | 0.18119 (12) | 0.0705 (4) | |
| O6 | 0.09069 (16) | 0.14894 (15) | 0.86339 (14) | 0.0818 (5) | |
| O4 | 0.64923 (18) | 0.37076 (15) | 0.19747 (13) | 0.0818 (5) | |
| O5 | 0.22910 (15) | 0.30002 (18) | 0.87163 (17) | 0.0998 (8) | |
| H1 | 0.6674 (14) | 0.4000 (15) | 0.9771 (12) | 0.046 (5)* | |
| H19 | 0.941 (2) | 0.562 (2) | 0.0823 (17) | 0.089 (9)* | |
| H18 | 0.876 (2) | 0.503 (2) | 0.0403 (18) | 0.099 (10)* | |
| H20 | 0.578 (2) | 0.534 (2) | 0.0649 (17) | 0.089 (9)* | |
| H21 | 0.625 (2) | 0.461 (2) | 0.1060 (18) | 0.091 (9)* | |
| H23 | 0.906 (2) | 0.349 (2) | 0.2174 (19) | 0.091 (11)* | |
| H22 | 0.880 (2) | 0.404 (2) | 0.1587 (18) | 0.095 (10)* | |
| H25 | 0.630 (2) | 0.371 (2) | 0.245 (2) | 0.094 (11)* | |
| H24 | 0.710 (2) | 0.359 (2) | 0.1999 (19) | 0.101 (12)* | |
| H26 | 0.283 (2) | 0.297 (2) | 0.8633 (17) | 0.091 (10)* | |
| H28 | 0.133 (2) | 0.193 (2) | 0.8757 (16) | 0.082 (9)* | |
| H2 | 0.6373 (16) | 0.2133 (16) | 0.7053 (12) | 0.061 (6)* | |
| H3 | 0.6782 (16) | 0.2259 (17) | 0.5682 (14) | 0.067 (6)* | |
| H4 | 0.8253 (18) | 0.1469 (17) | 0.5331 (15) | 0.077 (7)* | |
| H5 | 0.9156 (16) | 0.0511 (16) | 0.6364 (13) | 0.066 (6)* | |
| H6 | 0.9746 (14) | −0.0575 (15) | 0.7262 (13) | 0.056 (5)* | |
| H7 | 1.0420 (16) | −0.1609 (16) | 0.8382 (12) | 0.062 (6)* | |
| H8 | 0.9863 (16) | −0.1419 (16) | 0.9707 (13) | 0.059 (6)* | |
| H9 | 0.8632 (13) | −0.0252 (13) | 0.9892 (11) | 0.041 (5)* | |
| H10 | 0.7829 (13) | 0.2045 (14) | 1.0568 (11) | 0.044 (5)* | |
| H11 | 0.7717 (15) | 0.1569 (15) | 1.1940 (12) | 0.053 (5)* | |
| H13 | 0.6198 (16) | −0.0869 (17) | 1.1047 (13) | 0.060 (6)* | |
| H12 | 0.6918 (16) | 0.0081 (16) | 1.2213 (14) | 0.069 (6)* | |
| H17 | 0.5993 (14) | −0.0226 (14) | 0.7453 (12) | 0.045 (5)* | |
| H14 | 0.5487 (15) | −0.1618 (16) | 0.9997 (13) | 0.064 (6)* | |
| H16 | 0.5067 (17) | −0.1663 (17) | 0.7484 (14) | 0.070 (6)* | |
| H15 | 0.4802 (16) | −0.2377 (17) | 0.8765 (12) | 0.063 (6)* | |
| H29 | 0.035 (3) | 0.178 (3) | 0.867 (2) | 0.140 (14)* | |
| H27 | 0.211 (2) | 0.354 (2) | 0.8758 (18) | 0.085 (10)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.02916 (11) | 0.02725 (10) | 0.03302 (10) | 0.00047 (7) | 0.00869 (7) | −0.00243 (7) |
| C1 | 0.0313 (7) | 0.0298 (7) | 0.0387 (7) | 0.0022 (6) | 0.0115 (6) | 0.0013 (6) |
| N4 | 0.0325 (7) | 0.0364 (7) | 0.0510 (7) | 0.0043 (6) | 0.0117 (6) | 0.0013 (6) |
| N1 | 0.0278 (6) | 0.0312 (6) | 0.0409 (6) | −0.0003 (5) | 0.0068 (5) | −0.0021 (5) |
| N5 | 0.0341 (7) | 0.0356 (7) | 0.0580 (8) | 0.0006 (6) | 0.0104 (6) | −0.0175 (6) |
| N6 | 0.0273 (6) | 0.0320 (6) | 0.0414 (6) | −0.0015 (5) | 0.0105 (5) | −0.0013 (5) |
| N3 | 0.0302 (7) | 0.0423 (8) | 0.0548 (8) | 0.0015 (6) | 0.0082 (6) | 0.0030 (6) |
| N7 | 0.0288 (7) | 0.0444 (8) | 0.0563 (8) | −0.0037 (6) | 0.0116 (6) | −0.0054 (6) |
| N2 | 0.0300 (7) | 0.0394 (7) | 0.0479 (7) | −0.0021 (5) | 0.0052 (5) | −0.0005 (6) |
| N8 | 0.0349 (8) | 0.0490 (9) | 0.0764 (11) | −0.0098 (6) | 0.0116 (7) | −0.0122 (8) |
| N9 | 0.0372 (8) | 0.0396 (8) | 0.0695 (10) | −0.0077 (6) | 0.0076 (7) | −0.0122 (7) |
| C2 | 0.0318 (7) | 0.0307 (7) | 0.0391 (7) | −0.0024 (6) | 0.0062 (6) | −0.0025 (6) |
| N10 | 0.0425 (7) | 0.0379 (7) | 0.0365 (6) | 0.0035 (6) | 0.0104 (5) | −0.0026 (5) |
| N11 | 0.0317 (6) | 0.0312 (6) | 0.0421 (7) | 0.0007 (5) | 0.0056 (5) | −0.0058 (5) |
| C8 | 0.0315 (8) | 0.0366 (8) | 0.0455 (8) | −0.0032 (6) | 0.0078 (6) | −0.0137 (6) |
| C7 | 0.0403 (8) | 0.0355 (8) | 0.0413 (8) | −0.0045 (7) | 0.0123 (6) | −0.0109 (6) |
| N12 | 0.0324 (6) | 0.0323 (6) | 0.0358 (6) | −0.0006 (5) | 0.0079 (5) | −0.0006 (5) |
| C11 | 0.0412 (10) | 0.0439 (10) | 0.0665 (12) | 0.0080 (8) | −0.0095 (9) | −0.0068 (9) |
| C3 | 0.0660 (13) | 0.0539 (11) | 0.0440 (9) | 0.0177 (10) | 0.0129 (9) | 0.0037 (8) |
| C12 | 0.0371 (9) | 0.0402 (9) | 0.0507 (9) | 0.0039 (7) | 0.0017 (7) | −0.0030 (7) |
| C9 | 0.0394 (9) | 0.0593 (11) | 0.0577 (11) | 0.0069 (8) | 0.0084 (8) | −0.0232 (9) |
| C6 | 0.0604 (12) | 0.0584 (11) | 0.0481 (10) | −0.0001 (10) | 0.0239 (9) | −0.0107 (9) |
| C10 | 0.0385 (10) | 0.0538 (11) | 0.0772 (13) | 0.0144 (8) | −0.0044 (9) | −0.0243 (10) |
| C4 | 0.0919 (17) | 0.0631 (13) | 0.0416 (10) | 0.0147 (12) | 0.0109 (10) | 0.0073 (9) |
| C5 | 0.0970 (18) | 0.0636 (13) | 0.0410 (10) | 0.0010 (12) | 0.0279 (11) | −0.0031 (9) |
| N13 | 0.0343 (7) | 0.0322 (6) | 0.0421 (7) | −0.0016 (5) | 0.0060 (5) | −0.0054 (5) |
| C14 | 0.0502 (10) | 0.0561 (11) | 0.0358 (8) | −0.0015 (8) | 0.0040 (7) | −0.0024 (8) |
| C18 | 0.0318 (8) | 0.0304 (8) | 0.0497 (9) | 0.0006 (6) | 0.0086 (6) | −0.0002 (6) |
| C13 | 0.0438 (9) | 0.0386 (8) | 0.0378 (8) | −0.0037 (7) | 0.0058 (7) | −0.0018 (6) |
| C17 | 0.0319 (7) | 0.0324 (8) | 0.0430 (8) | 0.0005 (6) | 0.0089 (6) | 0.0029 (6) |
| C22 | 0.0500 (10) | 0.0481 (10) | 0.0485 (10) | −0.0061 (8) | 0.0068 (8) | −0.0110 (8) |
| C16 | 0.0569 (11) | 0.0462 (10) | 0.0521 (10) | −0.0092 (9) | 0.0103 (8) | 0.0127 (8) |
| C15 | 0.0621 (12) | 0.0648 (12) | 0.0390 (9) | −0.0037 (10) | 0.0081 (8) | 0.0115 (8) |
| C19 | 0.0504 (11) | 0.0377 (9) | 0.0639 (11) | −0.0091 (8) | 0.0094 (9) | 0.0029 (8) |
| C20 | 0.0549 (11) | 0.0380 (10) | 0.0821 (14) | −0.0139 (9) | 0.0092 (10) | −0.0080 (9) |
| C21 | 0.0547 (12) | 0.0534 (11) | 0.0675 (13) | −0.0126 (9) | 0.0043 (10) | −0.0251 (10) |
| O1 | 0.0485 (8) | 0.0625 (9) | 0.0674 (9) | −0.0159 (7) | 0.0111 (7) | −0.0119 (7) |
| O2 | 0.0947 (13) | 0.0624 (10) | 0.0601 (9) | 0.0376 (9) | 0.0285 (8) | 0.0006 (7) |
| O3 | 0.0740 (11) | 0.0698 (11) | 0.0654 (10) | −0.0050 (9) | −0.0035 (9) | 0.0078 (8) |
| O6 | 0.0624 (11) | 0.0695 (11) | 0.1171 (15) | −0.0019 (10) | 0.0259 (11) | −0.0158 (10) |
| O4 | 0.0784 (14) | 0.0903 (13) | 0.0747 (12) | −0.0025 (10) | −0.0016 (10) | 0.0195 (10) |
| O5 | 0.0458 (10) | 0.0870 (15) | 0.169 (2) | −0.0099 (10) | 0.0244 (12) | −0.0504 (14) |
| Ni1—N6 | 2.0624 (12) | C6—H5 | 0.92 (2) |
| Ni1—N10 | 2.0754 (13) | C10—H7 | 0.92 (2) |
| Ni1—N1 | 2.0800 (12) | C4—C5 | 1.369 (3) |
| Ni1—N13 | 2.0941 (13) | C4—H3 | 0.93 (2) |
| Ni1—N12 | 2.0968 (12) | C5—H4 | 0.95 (2) |
| Ni1—N11 | 2.1070 (12) | N13—C22 | 1.339 (2) |
| C1—N4 | 1.3322 (19) | N13—C18 | 1.346 (2) |
| C1—N1 | 1.3340 (18) | C14—C15 | 1.363 (3) |
| C1—N5 | 1.363 (2) | C14—C13 | 1.376 (2) |
| N4—N3 | 1.3502 (19) | C14—H11 | 0.91 (2) |
| N1—N2 | 1.3589 (17) | C18—C19 | 1.386 (2) |
| N5—C2 | 1.3732 (19) | C18—C17 | 1.483 (2) |
| N5—H1 | 0.794 (19) | C13—H10 | 0.931 (19) |
| N6—C2 | 1.3348 (19) | C17—C16 | 1.389 (2) |
| N6—N7 | 1.3551 (17) | C22—C21 | 1.379 (3) |
| N3—N2 | 1.3007 (19) | C22—H17 | 0.930 (18) |
| N7—N8 | 1.299 (2) | C16—C15 | 1.376 (3) |
| N8—N9 | 1.349 (2) | C16—H13 | 0.94 (2) |
| N9—C2 | 1.325 (2) | C15—H12 | 0.93 (2) |
| N10—C3 | 1.333 (2) | C19—C20 | 1.372 (3) |
| N10—C7 | 1.345 (2) | C19—H14 | 0.94 (2) |
| N11—C12 | 1.334 (2) | C20—C21 | 1.371 (3) |
| N11—C8 | 1.3470 (19) | C20—H15 | 0.93 (2) |
| C8—C9 | 1.388 (2) | C21—H16 | 0.91 (2) |
| C8—C7 | 1.481 (2) | O1—H19 | 0.81 (3) |
| C7—C6 | 1.387 (2) | O1—H18 | 0.86 (3) |
| N12—C13 | 1.341 (2) | O2—H20 | 0.80 (3) |
| N12—C17 | 1.3462 (19) | O2—H21 | 0.84 (3) |
| C11—C10 | 1.371 (3) | O3—H23 | 0.75 (3) |
| C11—C12 | 1.381 (2) | O3—H22 | 0.82 (3) |
| C11—H8 | 0.93 (2) | O6—H28 | 0.82 (3) |
| C3—C4 | 1.377 (3) | O6—H29 | 0.85 (4) |
| C3—H2 | 0.92 (2) | O4—H25 | 0.83 (3) |
| C12—H9 | 0.959 (17) | O4—H24 | 0.82 (3) |
| C9—C10 | 1.373 (3) | O5—H26 | 0.75 (3) |
| C9—H6 | 0.96 (2) | O5—H27 | 0.76 (3) |
| C6—C5 | 1.367 (3) | ||
| N6—Ni1—N10 | 91.81 (5) | N11—C12—C11 | 122.98 (17) |
| N6—Ni1—N1 | 83.67 (5) | N11—C12—H9 | 117.4 (10) |
| N10—Ni1—N1 | 96.27 (5) | C11—C12—H9 | 119.6 (10) |
| N6—Ni1—N13 | 171.13 (5) | C10—C9—C8 | 119.48 (17) |
| N10—Ni1—N13 | 96.89 (5) | C10—C9—H6 | 122.8 (12) |
| N1—Ni1—N13 | 93.61 (5) | C8—C9—H6 | 117.7 (12) |
| N6—Ni1—N12 | 93.24 (5) | C5—C6—C7 | 119.54 (19) |
| N10—Ni1—N12 | 170.80 (5) | C5—C6—H5 | 121.5 (13) |
| N1—Ni1—N12 | 91.93 (5) | C7—C6—H5 | 118.9 (13) |
| N13—Ni1—N12 | 78.39 (5) | C11—C10—C9 | 119.21 (17) |
| N6—Ni1—N11 | 95.69 (5) | C11—C10—H7 | 120.3 (13) |
| N10—Ni1—N11 | 78.48 (5) | C9—C10—H7 | 120.5 (13) |
| N1—Ni1—N11 | 174.71 (5) | C5—C4—C3 | 118.5 (2) |
| N13—Ni1—N11 | 87.78 (5) | C5—C4—H3 | 121.7 (13) |
| N12—Ni1—N11 | 93.35 (5) | C3—C4—H3 | 119.8 (14) |
| N4—C1—N1 | 111.99 (13) | C6—C5—C4 | 119.27 (18) |
| N4—C1—N5 | 122.95 (13) | C6—C5—H4 | 119.5 (14) |
| N1—C1—N5 | 125.04 (13) | C4—C5—H4 | 121.2 (14) |
| C1—N4—N3 | 104.10 (12) | C22—N13—C18 | 118.33 (14) |
| C1—N1—N2 | 104.66 (12) | C22—N13—Ni1 | 126.65 (12) |
| C1—N1—Ni1 | 125.53 (10) | C18—N13—Ni1 | 114.95 (10) |
| N2—N1—Ni1 | 128.02 (9) | C15—C14—C13 | 118.61 (17) |
| C1—N5—C2 | 123.02 (13) | C15—C14—H11 | 121.0 (13) |
| C1—N5—H1 | 117.5 (14) | C13—C14—H11 | 120.4 (13) |
| C2—N5—H1 | 118.9 (14) | N13—C18—C19 | 121.49 (16) |
| C2—N6—N7 | 104.61 (12) | N13—C18—C17 | 115.73 (13) |
| C2—N6—Ni1 | 127.34 (10) | C19—C18—C17 | 122.78 (15) |
| N7—N6—Ni1 | 127.80 (10) | N12—C13—C14 | 123.10 (16) |
| N2—N3—N4 | 110.50 (12) | N12—C13—H10 | 117.1 (11) |
| N8—N7—N6 | 108.62 (13) | C14—C13—H10 | 119.8 (11) |
| N3—N2—N1 | 108.74 (12) | N12—C17—C16 | 121.02 (15) |
| N7—N8—N9 | 110.61 (13) | N12—C17—C18 | 115.58 (13) |
| C2—N9—N8 | 104.00 (13) | C16—C17—C18 | 123.40 (15) |
| N9—C2—N6 | 112.16 (13) | N13—C22—C21 | 122.71 (18) |
| N9—C2—N5 | 123.47 (14) | N13—C22—H17 | 117.7 (11) |
| N6—C2—N5 | 124.35 (13) | C21—C22—H17 | 119.6 (11) |
| C3—N10—C7 | 118.20 (14) | C15—C16—C17 | 119.54 (17) |
| C3—N10—Ni1 | 125.93 (11) | C15—C16—H13 | 124.9 (13) |
| C7—N10—Ni1 | 115.52 (11) | C17—C16—H13 | 115.6 (13) |
| C12—N11—C8 | 118.31 (14) | C14—C15—C16 | 119.40 (17) |
| C12—N11—Ni1 | 126.95 (11) | C14—C15—H12 | 121.7 (14) |
| C8—N11—Ni1 | 114.38 (10) | C16—C15—H12 | 118.9 (14) |
| N11—C8—C9 | 121.38 (16) | C20—C19—C18 | 119.42 (18) |
| N11—C8—C7 | 115.65 (13) | C20—C19—H14 | 120.2 (13) |
| C9—C8—C7 | 122.92 (15) | C18—C19—H14 | 120.4 (13) |
| N10—C7—C6 | 121.32 (17) | C21—C20—C19 | 119.28 (18) |
| N10—C7—C8 | 115.33 (13) | C21—C20—H15 | 120.6 (13) |
| C6—C7—C8 | 123.34 (16) | C19—C20—H15 | 120.1 (13) |
| C13—N12—C17 | 118.28 (13) | C20—C21—C22 | 118.77 (19) |
| C13—N12—Ni1 | 126.68 (11) | C20—C21—H16 | 121.4 (14) |
| C17—N12—Ni1 | 114.86 (10) | C22—C21—H16 | 119.8 (15) |
| C10—C11—C12 | 118.62 (19) | H19—O1—H18 | 102 (2) |
| C10—C11—H8 | 122.1 (13) | H20—O2—H21 | 104 (3) |
| C12—C11—H8 | 119.3 (13) | H23—O3—H22 | 101 (3) |
| N10—C3—C4 | 123.09 (19) | H28—O6—H29 | 104 (3) |
| N10—C3—H2 | 115.6 (13) | H25—O4—H24 | 111 (3) |
| C4—C3—H2 | 121.3 (13) | H26—O5—H27 | 113 (3) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N5—H1···O2i | 0.794 (19) | 1.99 (2) | 2.770 (2) | 167.7 (19) |
| O1—H19···N8ii | 0.81 (3) | 2.09 (3) | 2.899 (2) | 174 (3) |
| O1—H18···N9iii | 0.86 (3) | 2.02 (3) | 2.864 (2) | 165 (3) |
| O2—H20···N4iv | 0.80 (3) | 2.08 (3) | 2.853 (2) | 161 (3) |
| O2—H21···O4 | 0.84 (3) | 1.90 (3) | 2.724 (3) | 168 (3) |
| O3—H23···N2v | 0.75 (3) | 2.26 (3) | 2.981 (2) | 163 (3) |
| O3—H22···O1 | 0.82 (3) | 2.08 (3) | 2.885 (3) | 168 (3) |
| O4—H25···O6v | 0.83 (3) | 2.03 (3) | 2.849 (3) | 171 (3) |
| O4—H24···O3 | 0.82 (3) | 2.12 (3) | 2.930 (3) | 167 (3) |
| Symmetry codes: (i) x, y, z+1; (ii) −x+2, −y+1, −z+1; (iii) x, y, z−1; (iv) −x+1, −y+1, −z+1; (v) x+1/2, −y+1/2, z−1/2. |
| Ni1—N6 | 2.0624 (12) | Ni1—N13 | 2.0941 (13) |
| Ni1—N10 | 2.0754 (13) | Ni1—N12 | 2.0968 (12) |
| Ni1—N1 | 2.0800 (12) | Ni1—N11 | 2.1070 (12) |
| N6—Ni1—N1 | 83.67 (5) | N10—Ni1—N12 | 170.80 (5) |
| N10—Ni1—N1 | 96.27 (5) | N13—Ni1—N12 | 78.39 (5) |
| N6—Ni1—N13 | 171.13 (5) | N1—Ni1—N11 | 174.71 (5) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N5—H1···O2i | 0.794 (19) | 1.99 (2) | 2.770 (2) | 167.7 (19) |
| O1—H19···N8ii | 0.81 (3) | 2.09 (3) | 2.899 (2) | 174 (3) |
| O1—H18···N9iii | 0.86 (3) | 2.02 (3) | 2.864 (2) | 165 (3) |
| O2—H20···N4iv | 0.80 (3) | 2.08 (3) | 2.853 (2) | 161 (3) |
| O2—H21···O4 | 0.84 (3) | 1.90 (3) | 2.724 (3) | 168 (3) |
| O3—H23···N2v | 0.75 (3) | 2.26 (3) | 2.981 (2) | 163 (3) |
| O3—H22···O1 | 0.82 (3) | 2.08 (3) | 2.885 (3) | 168 (3) |
| O4—H25···O6v | 0.83 (3) | 2.03 (3) | 2.849 (3) | 171 (3) |
| O4—H24···O3 | 0.82 (3) | 2.12 (3) | 2.930 (3) | 167 (3) |
| Symmetry codes: (i) x, y, z+1; (ii) −x+2, −y+1, −z+1; (iii) x, y, z−1; (iv) −x+1, −y+1, −z+1; (v) x+1/2, −y+1/2, z−1/2. |
The authors acknowledge financial support by the Open Fund of the Key Laboratory of Biological Resources Protection and Utilization of Hubei Province (grant Nos. 2007018 and 2007019).
Bruker (2003). SMART (Version 5.054) and SAINT-Plus (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2005). SHELXTL. Version 6.14. Bruker AXS Inc., Madison, Wisconsin, USA. [Please check original combined reference has been separated into the correct years]
Friedrich, M., Gólvez-Ruiz, J. C., Klapötke, T. M., Mayer, P., Weber, R. & Weigand, J. J. (2005). Inorg. Chem. 44, 8044–8052.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Metal complexes of N,N-bis-(1(2)H-tetrazol-5-yl)-amine have not been extensively examined even though the deprotonated ligand contains nine potentially electron-donating nitrogen atoms (Friedrich et al., 2005). The asymmetric unit of the title compound (I) comprises a Ni(II) cation, two 2,2'-bipyridine and one HBTA2− ligands and six solvent water molecules. Each NiII atom is coordinated to six N atoms from two 2,2'-bipyridine and one HBTA2− ligands to form a distorted mononuclear octahedral complex. (Table 1 and Fig. 1). In the crystal structure, an extensive range of O—H···N and O—H···O hydrogen bonds link the complex and water molecules into a three dimensional network, Table 2, Fig. 2.