In the title compound, [Ni(C3H10N2)(C6H18N4)](ClO4)2, the NiII atom has a distorted octahedral coordination, formed by four N atoms of the tris(2-aminoethyl)amine (tren) ligand and two N atoms of the 1,3-diaminopropane (pn) ligand. The tren ligand consists of three five-membered chelate rings in gauche conformations and the pn ligand consists of a six-membered chelate ring in a chair conformation. In the crystal structure, a two-dimensional network of hydrogen bonds extends parallel to the (100) plane.
Supporting information
CCDC reference: 283972
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.025
- wR factor = 0.062
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.06
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 4
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
PLAT410_ALERT_2_C Short Intra H...H Contact H4D .. H8BC .. 1.94 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B .. O5 .. 2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3B .. O2 .. 2.61 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 12
Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
correct. If it is not, please give the correct count in the
_publ_section_exptl_refinement section of the submitted CIF.
From the CIF: _diffrn_reflns_theta_max 28.29
From the CIF: _reflns_number_total 3745
Count of symmetry unique reflns 2460
Completeness (_total/calc) 152.24%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1285
Fraction of Friedel pairs measured 0.522
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
1 ALERT type 3 Indicator that the structure quality may be low
8 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
(1,3-Diaminopropane-
κ2N,
N')[tris(2-aminoethyl)amine-
κ4N,
N',
N'',
N''']nickel(II) bis(perchlorate)
top
Crystal data top
[Ni(C3H10N2)(C6H18N4)](ClO4)2 | Dx = 1.665 Mg m−3 |
Mr = 477.98 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 3745 reflections |
a = 16.876 (2) Å | θ = 2.4–28.3° |
b = 8.2937 (9) Å | µ = 1.35 mm−1 |
c = 13.6237 (16) Å | T = 295 K |
V = 1906.9 (4) Å3 | Plate, purple |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
F(000) = 1000 | |
Data collection top
Bruker CCD area-detector diffractometer | 3745 independent reflections |
Radiation source: fine-focus sealed tube | 3575 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 28.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −22→21 |
Tmin = 0.692, Tmax = 0.764 | k = −10→11 |
11557 measured reflections | l = −18→13 |
Refinement top
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)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.062 | w = 1/[σ2(Fo2) + (0.0371P)2 + 0.65P] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max = 0.026 |
3745 reflections | Δρmax = 0.44 e Å−3 |
245 parameters | Δρmin = −0.21 e Å−3 |
11 restraints | Absolute structure: Flack (1983), 1285 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.010 (12) |
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 | Occ. (<1) |
Ni | 0.163947 (14) | 0.04588 (3) | 0.50329 (3) | 0.02898 (7) | |
Cl1 | 0.28938 (4) | 0.48797 (7) | 0.65057 (6) | 0.04334 (14) | |
Cl2 | 0.08591 (4) | 0.49047 (7) | 0.29324 (5) | 0.04136 (14) | |
O1 | 0.21079 (17) | 0.5422 (4) | 0.6403 (3) | 0.0966 (11) | |
O2 | 0.29246 (19) | 0.3534 (3) | 0.7158 (2) | 0.0836 (8) | |
O3 | 0.3161 (2) | 0.4398 (3) | 0.5563 (2) | 0.0815 (8) | |
O4 | 0.33789 (18) | 0.6132 (4) | 0.6876 (2) | 0.0873 (9) | |
O5 | 0.16199 (14) | 0.4704 (4) | 0.3390 (2) | 0.0772 (8) | |
O6 | 0.03330 (14) | 0.3666 (3) | 0.3284 (2) | 0.0685 (7) | |
O7 | 0.05395 (17) | 0.6440 (3) | 0.3183 (2) | 0.0837 (8) | |
O8 | 0.09492 (15) | 0.4796 (3) | 0.1893 (2) | 0.0715 (7) | |
N1 | 0.21820 (12) | −0.1808 (3) | 0.46090 (19) | 0.0438 (5) | |
H1A | 0.1995 | −0.2577 | 0.5013 | 0.053* | |
H1B | 0.2011 | −0.2050 | 0.4001 | 0.053* | |
N2 | 0.25376 (11) | 0.1594 (2) | 0.42163 (17) | 0.0393 (5) | |
H2A | 0.2407 | 0.1513 | 0.3578 | 0.047* | |
H2B | 0.2528 | 0.2650 | 0.4369 | 0.047* | |
N3 | 0.08024 (12) | 0.0094 (3) | 0.38505 (17) | 0.0386 (5) | |
H3A | 0.0736 | 0.1022 | 0.3517 | 0.046* | |
H3B | 0.0991 | −0.0652 | 0.3432 | 0.046* | |
N4 | 0.11423 (13) | 0.2748 (3) | 0.53542 (18) | 0.0434 (5) | |
H4AA | 0.148 (3) | 0.358 (6) | 0.544 (5) | 0.052* | 0.60 |
H4AB | 0.079 (2) | 0.291 (6) | 0.487 (3) | 0.052* | 0.60 |
H4BA | 0.143 (5) | 0.326 (10) | 0.581 (5) | 0.052* | 0.40 |
H4BB | 0.125 (5) | 0.363 (7) | 0.499 (6) | 0.052* | 0.40 |
N5 | 0.06528 (12) | −0.0321 (3) | 0.58856 (16) | 0.0365 (5) | |
N6 | 0.22223 (13) | 0.0243 (3) | 0.64281 (19) | 0.0432 (5) | |
H6A | 0.2630 | −0.0452 | 0.6377 | 0.052* | |
H6B | 0.2417 | 0.1208 | 0.6609 | 0.052* | |
C1 | 0.30636 (16) | −0.1933 (3) | 0.4607 (3) | 0.0527 (7) | |
H1C | 0.3254 | −0.1835 | 0.5276 | 0.063* | |
H1D | 0.3212 | −0.2993 | 0.4369 | 0.063* | |
C2 | 0.34628 (16) | −0.0691 (4) | 0.3992 (3) | 0.0586 (8) | |
H2C | 0.3262 | −0.0783 | 0.3327 | 0.070* | |
H2D | 0.4025 | −0.0936 | 0.3972 | 0.070* | |
C3 | 0.33653 (14) | 0.1033 (4) | 0.4320 (3) | 0.0532 (7) | |
H3C | 0.3526 | 0.1127 | 0.5001 | 0.064* | |
H3D | 0.3710 | 0.1719 | 0.3932 | 0.064* | |
C4 | 0.00327 (15) | −0.0447 (4) | 0.4256 (2) | 0.0464 (6) | |
H4C | −0.0226 | −0.1161 | 0.3792 | 0.056* | |
H4D | −0.0309 | 0.0478 | 0.4362 | 0.056* | |
C5 | 0.01642 (14) | −0.1319 (3) | 0.5216 (2) | 0.0463 (7) | |
H5C | −0.0343 | −0.1547 | 0.5521 | 0.056* | |
H5D | 0.0429 | −0.2337 | 0.5093 | 0.056* | |
C6 | 0.09859 (16) | −0.1261 (4) | 0.6702 (2) | 0.0510 (7) | |
H6C | 0.1180 | −0.2287 | 0.6458 | 0.061* | |
H6D | 0.0576 | −0.1476 | 0.7183 | 0.061* | |
C7 | 0.16588 (18) | −0.0341 (4) | 0.7181 (2) | 0.0565 (8) | |
H7C | 0.1447 | 0.0569 | 0.7544 | 0.068* | |
H7D | 0.1933 | −0.1038 | 0.7641 | 0.068* | |
C8A | 0.0671 (3) | 0.2648 (6) | 0.6251 (4) | 0.0478 (11) | 0.60 |
H8AC | 0.034 (3) | 0.358 (6) | 0.631 (5) | 0.057* | 0.60 |
H8AD | 0.105 (3) | 0.262 (6) | 0.677 (3) | 0.057* | 0.60 |
C8B | 0.0313 (5) | 0.2584 (9) | 0.5647 (7) | 0.0527 (18) | 0.40 |
H8BC | 0.003 (4) | 0.243 (10) | 0.503 (3) | 0.063* | 0.40 |
H8BD | 0.018 (6) | 0.352 (9) | 0.604 (7) | 0.063* | 0.40 |
C9 | 0.01946 (15) | 0.1097 (4) | 0.6260 (2) | 0.0472 (6) | |
H9AC | −0.005 (3) | 0.110 (8) | 0.689 (2) | 0.057* | 0.60 |
H9AD | −0.025 (3) | 0.115 (7) | 0.582 (4) | 0.057* | 0.60 |
H9BC | −0.033 (2) | 0.066 (10) | 0.630 (8) | 0.057* | 0.40 |
H9BD | 0.031 (5) | 0.112 (12) | 0.6948 (19) | 0.057* | 0.40 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni | 0.02662 (11) | 0.03236 (12) | 0.02796 (13) | 0.00083 (9) | 0.00135 (12) | 0.00104 (13) |
Cl1 | 0.0471 (3) | 0.0383 (3) | 0.0446 (3) | −0.0023 (2) | −0.0057 (3) | 0.0000 (3) |
Cl2 | 0.0413 (3) | 0.0392 (3) | 0.0436 (3) | 0.0054 (2) | 0.0034 (3) | 0.0042 (3) |
O1 | 0.0582 (14) | 0.093 (2) | 0.138 (3) | 0.0204 (14) | −0.0058 (17) | 0.018 (2) |
O2 | 0.128 (2) | 0.0509 (14) | 0.0721 (19) | 0.0054 (14) | −0.0105 (17) | 0.0173 (13) |
O3 | 0.109 (2) | 0.0793 (18) | 0.0561 (19) | −0.0054 (16) | 0.0054 (15) | −0.0177 (13) |
O4 | 0.117 (2) | 0.0747 (17) | 0.0700 (19) | −0.0396 (16) | −0.0225 (16) | −0.0083 (15) |
O5 | 0.0519 (13) | 0.106 (2) | 0.073 (2) | −0.0015 (12) | −0.0136 (11) | 0.0234 (16) |
O6 | 0.0599 (12) | 0.0585 (13) | 0.0871 (19) | −0.0121 (10) | 0.0004 (12) | 0.0161 (12) |
O7 | 0.0987 (19) | 0.0483 (13) | 0.104 (2) | 0.0157 (12) | 0.0226 (16) | −0.0069 (14) |
O8 | 0.0740 (15) | 0.0958 (18) | 0.0447 (14) | 0.0178 (13) | 0.0033 (12) | 0.0012 (12) |
N1 | 0.0422 (11) | 0.0395 (11) | 0.0496 (13) | 0.0031 (8) | 0.0021 (9) | −0.0001 (9) |
N2 | 0.0365 (10) | 0.0392 (10) | 0.0422 (12) | −0.0018 (8) | 0.0042 (9) | 0.0052 (9) |
N3 | 0.0394 (10) | 0.0455 (11) | 0.0310 (11) | 0.0016 (9) | −0.0010 (9) | −0.0006 (9) |
N4 | 0.0451 (11) | 0.0382 (11) | 0.0470 (13) | 0.0038 (9) | −0.0004 (10) | −0.0022 (10) |
N5 | 0.0315 (9) | 0.0461 (12) | 0.0318 (12) | 0.0005 (8) | 0.0048 (8) | 0.0004 (9) |
N6 | 0.0383 (11) | 0.0554 (13) | 0.0359 (12) | 0.0006 (9) | −0.0025 (9) | 0.0039 (10) |
C1 | 0.0465 (14) | 0.0491 (15) | 0.0624 (19) | 0.0177 (12) | 0.0057 (12) | 0.0032 (13) |
C2 | 0.0369 (13) | 0.070 (2) | 0.069 (2) | 0.0133 (13) | 0.0144 (13) | 0.0034 (17) |
C3 | 0.0338 (12) | 0.0610 (17) | 0.065 (2) | −0.0052 (11) | 0.0049 (12) | 0.0105 (16) |
C4 | 0.0329 (12) | 0.0607 (17) | 0.0458 (17) | −0.0030 (11) | −0.0030 (11) | −0.0110 (13) |
C5 | 0.0374 (11) | 0.0534 (14) | 0.0480 (18) | −0.0130 (10) | 0.0076 (10) | −0.0045 (12) |
C6 | 0.0468 (14) | 0.0627 (17) | 0.0434 (16) | −0.0028 (12) | 0.0082 (11) | 0.0174 (14) |
C7 | 0.0514 (16) | 0.085 (2) | 0.0332 (16) | 0.0004 (14) | −0.0028 (12) | 0.0135 (15) |
C8A | 0.046 (2) | 0.050 (3) | 0.048 (3) | 0.002 (2) | 0.005 (2) | −0.017 (2) |
C8B | 0.047 (4) | 0.049 (4) | 0.063 (5) | 0.018 (3) | 0.006 (4) | −0.012 (4) |
C9 | 0.0376 (12) | 0.0615 (17) | 0.0424 (16) | 0.0060 (12) | 0.0105 (11) | −0.0093 (13) |
Geometric parameters (Å, º) top
Ni—N2 | 2.103 (2) | N6—C7 | 1.480 (4) |
Ni—N4 | 2.122 (2) | N6—H6A | 0.9000 |
Ni—N5 | 2.131 (2) | N6—H6B | 0.9000 |
Ni—N6 | 2.148 (3) | C1—C2 | 1.488 (4) |
Ni—N3 | 2.164 (2) | C1—H1C | 0.9700 |
Ni—N1 | 2.169 (2) | C1—H1D | 0.9700 |
Cl1—O1 | 1.407 (3) | C2—C3 | 1.507 (5) |
Cl1—O4 | 1.416 (3) | C2—H2C | 0.9700 |
Cl1—O3 | 1.418 (3) | C2—H2D | 0.9700 |
Cl1—O2 | 1.428 (3) | C3—H3C | 0.9700 |
Cl2—O7 | 1.424 (2) | C3—H3D | 0.9700 |
Cl2—O8 | 1.428 (3) | C4—C5 | 1.511 (4) |
Cl2—O5 | 1.437 (2) | C4—H4C | 0.9700 |
Cl2—O6 | 1.440 (2) | C4—H4D | 0.9700 |
N1—C1 | 1.491 (3) | C5—H5C | 0.9700 |
N1—H1A | 0.9000 | C5—H5D | 0.9700 |
N1—H1B | 0.9000 | C6—C7 | 1.516 (4) |
N2—C3 | 1.479 (3) | C6—H6C | 0.9700 |
N2—H2A | 0.9000 | C6—H6D | 0.9700 |
N2—H2B | 0.9000 | C7—H7C | 0.9700 |
N3—C4 | 1.481 (3) | C7—H7D | 0.9700 |
N3—H3A | 0.9000 | C8A—C9 | 1.518 (6) |
N3—H3B | 0.9000 | C8A—H8AC | 0.96 (2) |
N4—C8A | 1.460 (6) | C8A—H8AD | 0.96 (2) |
N4—C8B | 1.462 (8) | C8B—C9 | 1.502 (9) |
N4—H4AA | 0.90 (2) | C8B—H8BC | 0.97 (2) |
N4—H4AB | 0.894 (19) | C8B—H8BD | 0.97 (2) |
N4—H4BA | 0.89 (2) | C9—H9AC | 0.96 (2) |
N4—H4BB | 0.90 (2) | C9—H9AD | 0.96 (2) |
N5—C6 | 1.470 (4) | C9—H9BC | 0.96 (2) |
N5—C5 | 1.482 (3) | C9—H9BD | 0.96 (2) |
N5—C9 | 1.497 (3) | | |
| | | |
N2—Ni—N4 | 89.62 (9) | H6A—N6—H6B | 108.1 |
N2—Ni—N5 | 170.99 (8) | C2—C1—N1 | 113.9 (2) |
N4—Ni—N5 | 81.39 (9) | C2—C1—H1C | 108.8 |
N2—Ni—N6 | 100.11 (9) | N1—C1—H1C | 108.8 |
N4—Ni—N6 | 94.20 (9) | C2—C1—H1D | 108.8 |
N5—Ni—N6 | 81.37 (8) | N1—C1—H1D | 108.8 |
N2—Ni—N3 | 98.01 (9) | H1C—C1—H1D | 107.7 |
N4—Ni—N3 | 91.17 (9) | C1—C2—C3 | 116.1 (3) |
N5—Ni—N3 | 81.56 (9) | C1—C2—H2C | 108.3 |
N6—Ni—N3 | 161.12 (8) | C3—C2—H2C | 108.3 |
N2—Ni—N1 | 86.73 (8) | C1—C2—H2D | 108.3 |
N4—Ni—N1 | 175.91 (10) | C3—C2—H2D | 108.3 |
N5—Ni—N1 | 102.23 (8) | H2C—C2—H2D | 107.4 |
N6—Ni—N1 | 88.28 (9) | N2—C3—C2 | 111.9 (2) |
N3—Ni—N1 | 87.50 (9) | N2—C3—H3C | 109.2 |
O1—Cl1—O4 | 110.3 (2) | C2—C3—H3C | 109.2 |
O1—Cl1—O3 | 107.4 (2) | N2—C3—H3D | 109.2 |
O4—Cl1—O3 | 110.20 (19) | C2—C3—H3D | 109.2 |
O1—Cl1—O2 | 110.2 (2) | H3C—C3—H3D | 107.9 |
O4—Cl1—O2 | 109.30 (19) | N3—C4—C5 | 109.8 (2) |
O3—Cl1—O2 | 109.39 (19) | N3—C4—H4C | 109.7 |
O7—Cl2—O8 | 109.53 (17) | C5—C4—H4C | 109.7 |
O7—Cl2—O5 | 109.77 (19) | N3—C4—H4D | 109.7 |
O8—Cl2—O5 | 109.14 (17) | C5—C4—H4D | 109.7 |
O7—Cl2—O6 | 108.95 (16) | H4C—C4—H4D | 108.2 |
O8—Cl2—O6 | 110.54 (16) | N5—C5—C4 | 110.3 (2) |
O5—Cl2—O6 | 108.90 (15) | N5—C5—H5C | 109.6 |
C1—N1—Ni | 118.79 (17) | C4—C5—H5C | 109.6 |
C1—N1—H1A | 107.6 | N5—C5—H5D | 109.6 |
Ni—N1—H1A | 107.6 | C4—C5—H5D | 109.6 |
C1—N1—H1B | 107.6 | H5C—C5—H5D | 108.1 |
Ni—N1—H1B | 107.6 | N5—C6—C7 | 110.2 (2) |
H1A—N1—H1B | 107.0 | N5—C6—H6C | 109.6 |
C3—N2—Ni | 119.29 (18) | C7—C6—H6C | 109.6 |
C3—N2—H2A | 107.5 | N5—C6—H6D | 109.6 |
Ni—N2—H2A | 107.5 | C7—C6—H6D | 109.6 |
C3—N2—H2B | 107.5 | H6C—C6—H6D | 108.1 |
Ni—N2—H2B | 107.5 | N6—C7—C6 | 110.3 (3) |
H2A—N2—H2B | 107.0 | N6—C7—H7C | 109.6 |
C4—N3—Ni | 109.73 (17) | C6—C7—H7C | 109.6 |
C4—N3—H3A | 109.7 | N6—C7—H7D | 109.6 |
Ni—N3—H3A | 109.7 | C6—C7—H7D | 109.6 |
C4—N3—H3B | 109.7 | H7C—C7—H7D | 108.1 |
Ni—N3—H3B | 109.7 | N4—C8A—C9 | 110.1 (3) |
H3A—N3—H3B | 108.2 | N4—C8A—H8AC | 110 (5) |
C8A—N4—Ni | 109.7 (2) | C9—C8A—H8AC | 112 (4) |
C8B—N4—Ni | 110.6 (3) | H4BA—C8A—H8AC | 105 (6) |
C8A—N4—H4AA | 106 (4) | N4—C8A—H8AD | 105 (3) |
Ni—N4—H4AA | 118 (4) | C9—C8A—H8AD | 109 (3) |
C8A—N4—H4AB | 106 (3) | H8AC—C8A—H8AD | 111 (5) |
Ni—N4—H4AB | 104 (3) | N4—C8B—C9 | 110.8 (5) |
H4AA—N4—H4AB | 113 (5) | N4—C8B—H8BC | 104 (5) |
C8B—N4—H4BA | 112 (6) | C9—C8B—H8BC | 108 (5) |
Ni—N4—H4BA | 111 (6) | N4—C8B—H8BD | 107 (7) |
C8B—N4—H4BB | 115 (5) | C9—C8B—H8BD | 109 (7) |
Ni—N4—H4BB | 122 (6) | H8BC—C8B—H8BD | 118 (7) |
H4BA—N4—H4BB | 84 (8) | N5—C9—C8B | 112.8 (3) |
C6—N5—C5 | 112.5 (2) | N5—C9—C8A | 112.9 (2) |
C6—N5—C9 | 110.9 (2) | N5—C9—H9AC | 122 (4) |
C5—N5—C9 | 111.2 (2) | C8A—C9—H9AC | 104 (4) |
C6—N5—Ni | 105.94 (15) | N5—C9—H9AD | 103 (4) |
C5—N5—Ni | 105.57 (15) | C8A—C9—H9AD | 112 (4) |
C9—N5—Ni | 110.53 (16) | H9AC—C9—H9AD | 103 (5) |
C7—N6—Ni | 110.28 (18) | N5—C9—H9BC | 101 (5) |
C7—N6—H6A | 109.6 | C8B—C9—H9BC | 118 (6) |
Ni—N6—H6A | 109.6 | N5—C9—H9BD | 104 (6) |
C7—N6—H6B | 109.6 | C8B—C9—H9BD | 120 (6) |
Ni—N6—H6B | 109.6 | H9BC—C9—H9BD | 98 (8) |
| | | |
N2—Ni—N1—C1 | 40.9 (2) | N2—Ni—N6—C7 | 172.4 (2) |
N5—Ni—N1—C1 | −140.2 (2) | N4—Ni—N6—C7 | 82.0 (2) |
N6—Ni—N1—C1 | −59.4 (2) | N5—Ni—N6—C7 | 1.4 (2) |
N3—Ni—N1—C1 | 139.0 (2) | N3—Ni—N6—C7 | −24.1 (4) |
N4—Ni—N2—C3 | 137.1 (2) | N1—Ni—N6—C7 | −101.3 (2) |
N6—Ni—N2—C3 | 42.9 (2) | Ni—N1—C1—C2 | −55.5 (3) |
N3—Ni—N2—C3 | −131.8 (2) | N1—C1—C2—C3 | 64.5 (4) |
N1—Ni—N2—C3 | −44.8 (2) | Ni—N2—C3—C2 | 62.6 (3) |
N2—Ni—N3—C4 | −170.02 (17) | C1—C2—C3—N2 | −67.4 (4) |
N4—Ni—N3—C4 | −80.24 (18) | Ni—N3—C4—C5 | −27.2 (3) |
N5—Ni—N3—C4 | 0.88 (17) | C6—N5—C5—C4 | −163.8 (2) |
N6—Ni—N3—C4 | 26.4 (4) | C9—N5—C5—C4 | 71.1 (3) |
N1—Ni—N3—C4 | 103.64 (18) | Ni—N5—C5—C4 | −48.7 (2) |
N2—Ni—N4—C8A | −156.4 (3) | N3—C4—C5—N5 | 51.8 (3) |
N5—Ni—N4—C8A | 24.3 (3) | C5—N5—C6—C7 | 163.4 (2) |
N6—Ni—N4—C8A | −56.3 (3) | C9—N5—C6—C7 | −71.5 (3) |
N3—Ni—N4—C8A | 105.6 (3) | Ni—N5—C6—C7 | 48.5 (3) |
N2—Ni—N4—C8B | 159.8 (4) | Ni—N6—C7—C6 | 24.2 (3) |
N5—Ni—N4—C8B | −19.5 (4) | N5—C6—C7—N6 | −49.5 (3) |
N6—Ni—N4—C8B | −100.1 (4) | Ni—N4—C8A—C8B | −99.0 (5) |
N3—Ni—N4—C8B | 61.8 (4) | C8B—N4—C8A—C9 | 57.6 (5) |
N4—Ni—N5—C6 | −122.52 (19) | Ni—N4—C8A—C9 | −41.4 (4) |
N6—Ni—N5—C6 | −26.90 (18) | Ni—N4—C8B—C8A | 96.7 (5) |
N3—Ni—N5—C6 | 145.00 (19) | Ni—N4—C8B—C9 | 37.7 (7) |
N1—Ni—N5—C6 | 59.44 (19) | C6—N5—C9—C8B | 140.7 (4) |
N4—Ni—N5—C5 | 117.97 (17) | C5—N5—C9—C8B | −93.3 (4) |
N6—Ni—N5—C5 | −146.41 (17) | Ni—N5—C9—C8B | 23.6 (5) |
N3—Ni—N5—C5 | 25.49 (15) | C6—N5—C9—C8A | 97.6 (3) |
N1—Ni—N5—C5 | −60.07 (17) | C5—N5—C9—C8A | −136.4 (3) |
N4—Ni—N5—C9 | −2.33 (18) | Ni—N5—C9—C8A | −19.6 (4) |
N6—Ni—N5—C9 | 93.29 (18) | N4—C8B—C9—N5 | −40.9 (7) |
N3—Ni—N5—C9 | −94.81 (19) | N4—C8A—C9—N5 | 40.7 (5) |
N1—Ni—N5—C9 | 179.63 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.90 | 2.53 | 3.357 (5) | 154 |
N1—H1B···O2ii | 0.90 | 2.56 | 3.356 (4) | 148 |
N2—H2B···O3 | 0.90 | 2.43 | 3.144 (4) | 137 |
N2—H2B···O5 | 0.90 | 2.65 | 3.212 (4) | 121 |
N3—H3A···O6 | 0.90 | 2.32 | 3.162 (4) | 156 |
N3—H3B···O7i | 0.90 | 2.55 | 3.196 (4) | 129 |
N3—H3B···O2ii | 0.90 | 2.61 | 3.407 (4) | 148 |
N4—H4AA···O1 | 0.90 | 2.28 | 3.100 (4) | 152 |
N4—H4AB···O6 | 0.89 | 2.38 | 3.224 (4) | 158 |
N4—H4BA···O1 | 0.89 | 2.28 | 3.100 (4) | 153 |
N4—H4BB···O5 | 0.90 | 2.44 | 3.232 (5) | 147 |
N6—H6A···O8iii | 0.90 | 2.51 | 3.172 (4) | 131 |
N6—H6B···O2 | 0.90 | 2.24 | 3.138 (4) | 176 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y−1/2, z−1/2; (iii) −x+1/2, y−1/2, z+1/2. |