Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058370/sj2411sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058370/sj2411Isup2.hkl |
CCDC reference: 672693
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.028
- wR factor = 0.075
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 30 Ang. PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 16 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N10 .. 5.02 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N11 .. 5.07 su PLAT245_ALERT_2_C U(iso) H27 Smaller than U(eq) O5 by ... 0.01 AngSq
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 2.12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Other complexes of the N,N-bis[1(2H)-tetrazol-5-yl]amine ligand are rare; for a related copper(II) complex, see: Friedrich et al. (2005).
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).
[Ni(C2HN9)(C10H8N2)2]·6H2O | F(000) = 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 = 1.0–27.5° |
b = 13.3741 (3) Å | µ = 0.75 mm−1 |
c = 15.9408 (3) Å | T = 296 K |
β = 96.166 (1)° | 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) |
Graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 27.5°, θmin = 1.9° |
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 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | All H-atom parameters refined |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0359P)2 + 0.8759P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.033 |
6503 reflections | Δρmax = 0.32 e Å−3 |
496 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | 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 |
[Ni(C2HN9)(C10H8N2)2]·6H2O | V = 2828.29 (10) Å3 |
Mr = 630.27 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.3435 (3) Å | µ = 0.75 mm−1 |
b = 13.3741 (3) Å | T = 296 K |
c = 15.9408 (3) Å | 0.25 × 0.25 × 0.13 mm |
β = 96.166 (1)° |
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 | 0 restraints |
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 |
496 parameters |
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 | ||
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. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C2HN9)(C10H8N2)2]·6H2O |
Mr | 630.27 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 13.3435 (3), 13.3741 (3), 15.9408 (3) |
β (°) | 96.166 (1) |
V (Å3) | 2828.29 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.75 |
Crystal size (mm) | 0.25 × 0.25 × 0.13 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.830, 0.907 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6514, 6503, 5453 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.075, 1.03 |
No. of reflections | 6503 |
No. of parameters | 496 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.32, −0.30 |
Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2005).
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. |
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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.