The Ni atom in the title complex, [Ni(C2H3O2)2(C15H13N5)] or [Ni(CH3COO)2(tpdaH2)] (tpdaH2 is tripyridyldiamine), has a distorted octahedral coordination geometry formed by the tridentate tpdaH2 ligand and two acetate groups. The tpdaH2 ligand is mer-coordinated, with the N atom of the central pyridine ring in the equatorial position and the N atoms of the peripheral pyridine rings in the axial positions. The remaining three equatorial positions are occupied by the O atoms of two acetate anions. The H atoms of both NH groups of the tpdaH2 ligand are involved in strong hydrogen bonds with O atoms of adjacent complex molecules to form a three-dimensional network.
Supporting information
CCDC reference: 605163
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.079
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Ni1 - O1 .. 13.44 su
Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O2 .. 5.37 su
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: APEX2; software used to prepare material for publication: APEX2.
[2,6-Bis(2-pyridylamino)pyridine]diacetylnickel(II)
top
Crystal data top
[Ni(C2H3O2)2(C15H13N5)] | F(000) = 912 |
Mr = 440.10 | Dx = 1.562 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8134 reflections |
a = 9.6135 (4) Å | θ = 2.1–29.1° |
b = 7.9969 (3) Å | µ = 1.08 mm−1 |
c = 24.4047 (9) Å | T = 273 K |
β = 93.942 (1)° | Block, blue |
V = 1871.75 (13) Å3 | 0.30 × 0.17 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker APEX-II area-detector diffractometer | 4296 independent reflections |
Radiation source: fine-focus sealed tube | 3478 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scan | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −12→12 |
Tmin = 0.80, Tmax = 0.89 | k = −10→10 |
21140 measured reflections | l = −31→31 |
Refinement top
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.039P)2 + 0.399P] where P = (Fo2 + 2Fc2)/3 |
4296 reflections | (Δ/σ)max = 0.001 |
264 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni1 | 0.19934 (2) | 0.72586 (3) | 0.373756 (9) | 0.03099 (8) | |
C5 | 0.17373 (19) | 0.5646 (2) | 0.26185 (7) | 0.0353 (4) | |
C11 | 0.0627 (2) | 0.7644 (2) | 0.47976 (8) | 0.0369 (4) | |
C6 | −0.04378 (19) | 0.5452 (2) | 0.31506 (7) | 0.0345 (4) | |
C10 | −0.08179 (19) | 0.6081 (2) | 0.40496 (7) | 0.0355 (4) | |
C1 | 0.3945 (2) | 0.6476 (3) | 0.29079 (8) | 0.0479 (5) | |
H1 | 0.4550 | 0.6955 | 0.3178 | 0.057* | |
C15 | 0.2683 (2) | 0.9067 (3) | 0.47728 (8) | 0.0472 (5) | |
H15 | 0.3435 | 0.9398 | 0.4578 | 0.057* | |
C13 | 0.1550 (3) | 0.9061 (3) | 0.55986 (9) | 0.0602 (6) | |
H13 | 0.1502 | 0.9384 | 0.5963 | 0.072* | |
C7 | −0.1757 (2) | 0.4767 (3) | 0.30658 (8) | 0.0460 (5) | |
H7 | −0.2050 | 0.4307 | 0.2727 | 0.055* | |
C12 | 0.0532 (2) | 0.8099 (3) | 0.53506 (8) | 0.0501 (5) | |
H12 | −0.0218 | 0.7745 | 0.5543 | 0.060* | |
C8 | −0.2626 (2) | 0.4775 (3) | 0.34885 (9) | 0.0547 (6) | |
H8 | −0.3519 | 0.4327 | 0.3439 | 0.066* | |
C9 | −0.2169 (2) | 0.5447 (3) | 0.39828 (9) | 0.0510 (5) | |
H9 | −0.2751 | 0.5481 | 0.4271 | 0.061* | |
C3 | 0.3589 (2) | 0.5200 (3) | 0.20363 (9) | 0.0570 (6) | |
H3 | 0.3926 | 0.4832 | 0.1709 | 0.068* | |
C14 | 0.2661 (3) | 0.9561 (3) | 0.53069 (9) | 0.0568 (6) | |
H14 | 0.3374 | 1.0215 | 0.5470 | 0.068* | |
C2 | 0.4484 (2) | 0.5925 (3) | 0.24386 (10) | 0.0598 (6) | |
H2 | 0.5431 | 0.6031 | 0.2389 | 0.072* | |
C16 | 0.2260 (2) | 1.0244 (2) | 0.34231 (7) | 0.0391 (4) | |
C17 | 0.2289 (3) | 1.2074 (3) | 0.32859 (10) | 0.0573 (6) | |
H17A | 0.3204 | 1.2512 | 0.3380 | 0.086* | |
H17B | 0.1621 | 1.2656 | 0.3490 | 0.086* | |
H17C | 0.2062 | 1.2223 | 0.2900 | 0.086* | |
N5 | 0.16778 (16) | 0.81270 (19) | 0.45089 (6) | 0.0355 (3) | |
N3 | 0.00672 (15) | 0.60883 (18) | 0.36407 (6) | 0.0311 (3) | |
N1 | 0.25822 (15) | 0.63636 (19) | 0.30026 (6) | 0.0355 (3) | |
N4 | −0.04509 (17) | 0.6689 (2) | 0.45670 (6) | 0.0420 (4) | |
H4A | −0.1034 | 0.6404 | 0.4802 | 0.050* | |
N2 | 0.03451 (16) | 0.5458 (2) | 0.26919 (6) | 0.0422 (4) | |
H2A | −0.0152 | 0.5313 | 0.2389 | 0.051* | |
O1 | 0.33315 (14) | 0.95037 (17) | 0.36179 (6) | 0.0455 (3) | |
O3 | 0.34737 (13) | 0.56604 (17) | 0.40651 (5) | 0.0421 (3) | |
O2 | 0.11126 (14) | 0.94624 (17) | 0.33431 (5) | 0.0418 (3) | |
C18 | 0.3271 (2) | 0.4520 (2) | 0.44091 (8) | 0.0389 (4) | |
C19 | 0.4473 (2) | 0.3345 (3) | 0.45479 (10) | 0.0571 (6) | |
H19A | 0.4534 | 0.3117 | 0.4935 | 0.086* | |
H19B | 0.5325 | 0.3853 | 0.4448 | 0.086* | |
H19C | 0.4324 | 0.2319 | 0.4349 | 0.086* | |
O4 | 0.21566 (16) | 0.4277 (2) | 0.46161 (6) | 0.0595 (4) | |
C4 | 0.2223 (2) | 0.5035 (3) | 0.21243 (8) | 0.0472 (5) | |
H4 | 0.1613 | 0.4527 | 0.1863 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.03277 (13) | 0.03287 (14) | 0.02749 (13) | −0.00123 (9) | 0.00332 (9) | 0.00252 (9) |
C5 | 0.0421 (10) | 0.0353 (10) | 0.0290 (9) | 0.0037 (8) | 0.0051 (8) | 0.0041 (7) |
C11 | 0.0440 (11) | 0.0360 (10) | 0.0310 (9) | 0.0049 (8) | 0.0035 (8) | 0.0010 (7) |
C6 | 0.0387 (10) | 0.0341 (9) | 0.0309 (9) | −0.0008 (8) | 0.0028 (7) | 0.0020 (7) |
C10 | 0.0383 (10) | 0.0376 (10) | 0.0311 (9) | −0.0014 (8) | 0.0054 (8) | 0.0018 (7) |
C1 | 0.0388 (11) | 0.0605 (14) | 0.0448 (12) | −0.0002 (10) | 0.0068 (9) | −0.0018 (10) |
C15 | 0.0514 (12) | 0.0500 (12) | 0.0400 (11) | −0.0078 (10) | 0.0003 (9) | −0.0008 (9) |
C13 | 0.0809 (17) | 0.0678 (16) | 0.0313 (11) | −0.0005 (13) | 0.0000 (11) | −0.0104 (10) |
C7 | 0.0460 (11) | 0.0534 (13) | 0.0382 (11) | −0.0134 (10) | −0.0008 (9) | −0.0025 (9) |
C12 | 0.0581 (13) | 0.0601 (14) | 0.0330 (10) | −0.0001 (11) | 0.0089 (9) | −0.0038 (9) |
C8 | 0.0404 (11) | 0.0721 (16) | 0.0514 (13) | −0.0202 (11) | 0.0024 (10) | −0.0017 (11) |
C9 | 0.0401 (11) | 0.0695 (15) | 0.0448 (12) | −0.0118 (10) | 0.0136 (9) | −0.0007 (10) |
C3 | 0.0588 (14) | 0.0735 (16) | 0.0407 (12) | 0.0162 (12) | 0.0175 (10) | 0.0010 (11) |
C14 | 0.0645 (15) | 0.0618 (15) | 0.0427 (12) | −0.0084 (12) | −0.0070 (11) | −0.0066 (10) |
C2 | 0.0427 (12) | 0.0857 (18) | 0.0528 (14) | 0.0071 (12) | 0.0170 (11) | 0.0039 (12) |
C16 | 0.0526 (12) | 0.0376 (10) | 0.0278 (9) | −0.0006 (9) | 0.0079 (8) | 0.0018 (7) |
C17 | 0.0870 (18) | 0.0354 (11) | 0.0495 (13) | −0.0043 (11) | 0.0052 (12) | 0.0042 (9) |
N5 | 0.0409 (9) | 0.0354 (8) | 0.0304 (8) | −0.0002 (7) | 0.0032 (7) | 0.0015 (6) |
N3 | 0.0336 (8) | 0.0313 (8) | 0.0287 (7) | −0.0019 (6) | 0.0028 (6) | 0.0018 (6) |
N1 | 0.0351 (8) | 0.0393 (9) | 0.0326 (8) | 0.0012 (7) | 0.0060 (6) | 0.0019 (6) |
N4 | 0.0434 (9) | 0.0518 (10) | 0.0322 (8) | −0.0055 (8) | 0.0129 (7) | 0.0004 (7) |
N2 | 0.0383 (9) | 0.0603 (11) | 0.0276 (8) | −0.0029 (8) | 0.0005 (7) | −0.0033 (7) |
O1 | 0.0460 (8) | 0.0460 (8) | 0.0445 (8) | −0.0041 (6) | 0.0034 (6) | 0.0025 (6) |
O3 | 0.0423 (7) | 0.0432 (8) | 0.0412 (7) | 0.0036 (6) | 0.0048 (6) | 0.0115 (6) |
O2 | 0.0470 (8) | 0.0411 (8) | 0.0369 (7) | 0.0007 (6) | 0.0007 (6) | 0.0066 (6) |
C18 | 0.0435 (11) | 0.0408 (11) | 0.0320 (10) | −0.0012 (8) | 0.0012 (8) | 0.0013 (8) |
C19 | 0.0530 (13) | 0.0515 (13) | 0.0658 (15) | 0.0040 (11) | −0.0032 (11) | 0.0174 (11) |
O4 | 0.0562 (9) | 0.0663 (10) | 0.0587 (10) | 0.0046 (8) | 0.0238 (8) | 0.0189 (8) |
C4 | 0.0563 (13) | 0.0559 (13) | 0.0299 (10) | 0.0050 (10) | 0.0059 (9) | −0.0019 (9) |
Geometric parameters (Å, º) top
Ni1—O3 | 2.0350 (13) | C7—C8 | 1.372 (3) |
Ni1—N1 | 2.0467 (15) | C7—H7 | 0.9300 |
Ni1—N5 | 2.0485 (15) | C12—H12 | 0.9300 |
Ni1—N3 | 2.0737 (14) | C8—C9 | 1.366 (3) |
Ni1—O2 | 2.1535 (13) | C8—H8 | 0.9300 |
Ni1—O1 | 2.2394 (14) | C9—H9 | 0.9300 |
C5—N1 | 1.328 (2) | C3—C4 | 1.352 (3) |
C5—N2 | 1.371 (2) | C3—C2 | 1.387 (3) |
C5—C4 | 1.410 (3) | C3—H3 | 0.9300 |
C11—N5 | 1.328 (2) | C14—H14 | 0.9300 |
C11—N4 | 1.376 (3) | C2—H2 | 0.9300 |
C11—C12 | 1.407 (3) | C16—O1 | 1.253 (2) |
C6—N3 | 1.358 (2) | C16—O2 | 1.271 (2) |
C6—C7 | 1.384 (3) | C16—C17 | 1.502 (3) |
C6—N2 | 1.391 (2) | C17—H17A | 0.9600 |
C10—N3 | 1.355 (2) | C17—H17B | 0.9600 |
C10—N4 | 1.376 (2) | C17—H17C | 0.9600 |
C10—C9 | 1.393 (3) | N4—H4A | 0.8600 |
C1—N1 | 1.349 (2) | N2—H2A | 0.8600 |
C1—C2 | 1.362 (3) | O3—C18 | 1.264 (2) |
C1—H1 | 0.9300 | C18—O4 | 1.231 (2) |
C15—N5 | 1.352 (2) | C18—C19 | 1.509 (3) |
C15—C14 | 1.363 (3) | C19—H19A | 0.9600 |
C15—H15 | 0.9300 | C19—H19B | 0.9600 |
C13—C12 | 1.355 (3) | C19—H19C | 0.9600 |
C13—C14 | 1.383 (3) | C4—H4 | 0.9300 |
C13—H13 | 0.9300 | | |
| | | |
O3—Ni1—N1 | 84.06 (6) | C4—C3—C2 | 119.4 (2) |
O3—Ni1—N5 | 89.75 (6) | C4—C3—H3 | 120.3 |
N1—Ni1—N5 | 172.37 (6) | C2—C3—H3 | 120.3 |
O3—Ni1—N3 | 110.87 (6) | C15—C14—C13 | 118.2 (2) |
N1—Ni1—N3 | 92.34 (6) | C15—C14—H14 | 120.9 |
N5—Ni1—N3 | 94.03 (6) | C13—C14—H14 | 120.9 |
O3—Ni1—O2 | 158.82 (5) | C1—C2—C3 | 118.5 (2) |
N1—Ni1—O2 | 91.05 (6) | C1—C2—H2 | 120.7 |
N5—Ni1—O2 | 93.14 (6) | C3—C2—H2 | 120.7 |
N3—Ni1—O2 | 89.87 (5) | O1—C16—O2 | 120.54 (17) |
O3—Ni1—O1 | 99.34 (5) | O1—C16—C17 | 121.1 (2) |
N1—Ni1—O1 | 88.29 (6) | O2—C16—C17 | 118.32 (19) |
N5—Ni1—O1 | 88.32 (6) | C16—C17—H17A | 109.5 |
N3—Ni1—O1 | 149.70 (5) | C16—C17—H17B | 109.5 |
O2—Ni1—O1 | 59.82 (5) | H17A—C17—H17B | 109.5 |
N1—C5—N2 | 120.68 (16) | C16—C17—H17C | 109.5 |
N1—C5—C4 | 122.09 (18) | H17A—C17—H17C | 109.5 |
N2—C5—C4 | 117.23 (17) | H17B—C17—H17C | 109.5 |
N5—C11—N4 | 121.55 (17) | C11—N5—C15 | 116.99 (17) |
N5—C11—C12 | 122.38 (19) | C11—N5—Ni1 | 123.70 (13) |
N4—C11—C12 | 116.06 (18) | C15—N5—Ni1 | 118.69 (13) |
N3—C6—C7 | 123.25 (17) | C10—N3—C6 | 116.25 (15) |
N3—C6—N2 | 121.79 (16) | C10—N3—Ni1 | 121.27 (12) |
C7—C6—N2 | 114.96 (16) | C6—N3—Ni1 | 122.11 (12) |
N3—C10—N4 | 122.66 (16) | C5—N1—C1 | 117.51 (17) |
N3—C10—C9 | 122.88 (17) | C5—N1—Ni1 | 125.26 (12) |
N4—C10—C9 | 114.46 (17) | C1—N1—Ni1 | 117.21 (13) |
N1—C1—C2 | 123.5 (2) | C11—N4—C10 | 135.22 (16) |
N1—C1—H1 | 118.2 | C11—N4—H4A | 112.4 |
C2—C1—H1 | 118.2 | C10—N4—H4A | 112.4 |
N5—C15—C14 | 124.0 (2) | C5—N2—C6 | 133.85 (16) |
N5—C15—H15 | 118.0 | C5—N2—H2A | 113.1 |
C14—C15—H15 | 118.0 | C6—N2—H2A | 113.1 |
C12—C13—C14 | 119.6 (2) | C16—O1—Ni1 | 87.90 (11) |
C12—C13—H13 | 120.2 | C18—O3—Ni1 | 125.37 (12) |
C14—C13—H13 | 120.2 | C16—O2—Ni1 | 91.34 (11) |
C8—C7—C6 | 119.01 (18) | O4—C18—O3 | 124.36 (18) |
C8—C7—H7 | 120.5 | O4—C18—C19 | 118.97 (18) |
C6—C7—H7 | 120.5 | O3—C18—C19 | 116.61 (17) |
C13—C12—C11 | 118.9 (2) | C18—C19—H19A | 109.5 |
C13—C12—H12 | 120.6 | C18—C19—H19B | 109.5 |
C11—C12—H12 | 120.6 | H19A—C19—H19B | 109.5 |
C9—C8—C7 | 119.36 (19) | C18—C19—H19C | 109.5 |
C9—C8—H8 | 120.3 | H19A—C19—H19C | 109.5 |
C7—C8—H8 | 120.3 | H19B—C19—H19C | 109.5 |
C8—C9—C10 | 119.20 (19) | C3—C4—C5 | 119.0 (2) |
C8—C9—H9 | 120.4 | C3—C4—H4 | 120.5 |
C10—C9—H9 | 120.4 | C5—C4—H4 | 120.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2i | 0.86 | 2.07 | 2.9139 (19) | 167 |
N4—H4A···O4ii | 0.86 | 1.92 | 2.777 (2) | 174 |
C12—H12···O4ii | 0.93 | 2.48 | 3.212 (3) | 136 |
C15—H15···O1 | 0.93 | 2.34 | 2.949 (2) | 123 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y+1, −z+1. |