In the title compound, [N(C
4H
12N
2)(C
6H
18N
4)](ClO
4)
2, the Ni
II atom is coordinated in a distorted octahedron by four N atoms of the tris(2-aminoethyl)amine (tren) ligand and by two N atoms of the 2-methylpropane-1,2-diamine (2-Mepn) ligand. The primary amino group of 2-Mepn at the C-2 position occupies the position
trans to the tertiary amino group of tren. The complex cations and perchlorate anions are linked
via N—H
O hydrogen bonds, forming one-dimensional zigzag chains along the [101] direction.
Supporting information
CCDC reference: 277735
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.008 Å
- Disorder in main residue
- R factor = 0.039
- wR factor = 0.116
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Ni
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O5
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O6A
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O7A
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O4A
PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for O4B
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 23.00 Perc.
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O7B
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT410_ALERT_2_C Short Intra H...H Contact H4C .. H6BD .. 1.96 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor N6 - H6A ... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6A .. O8 .. 2.65 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
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 28.30
From the CIF: _reflns_number_total 4172
Count of symmetry unique reflns 2584
Completeness (_total/calc) 161.46%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1588
Fraction of Friedel pairs measured 0.615
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
19 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
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
12 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.
(2-Methylpropane-1,2-diamine-
κ2N,
N')[tris(2-aminoehtttyl)amine-
κ4N,
N',
N'',
N''')nickel(II) diperchlorate
top
Crystal data top
[Ni(C4H12N2)(C6H18N4)](ClO4)2 | F(000) = 1032 |
Mr = 492.01 | Dx = 1.572 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
a = 14.532 (2) Å | Cell parameters from 6541 reflections |
b = 9.7074 (13) Å | θ = 2.5–28.3° |
c = 14.823 (2) Å | µ = 1.24 mm−1 |
β = 96.167 (2)° | T = 295 K |
V = 2079.0 (5) Å3 | Plate, light violet |
Z = 4 | 0.25 × 0.20 × 0.08 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4172 independent reflections |
Radiation source: fine-focus sealed tube | 3560 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 28.3°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −17→18 |
Tmin = 0.780, Tmax = 0.906 | k = −6→12 |
6541 measured reflections | l = −19→18 |
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)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0953P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.91 | (Δ/σ)max = 0.016 |
4172 reflections | Δρmax = 0.34 e Å−3 |
290 parameters | Δρmin = −0.40 e Å−3 |
78 restraints | Absolute structure: Flack (1983), 1588 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (2) |
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 | 0.16876 (6) | 0.25478 (4) | 0.23727 (6) | 0.03168 (12) | |
Cl1 | 0.10912 (13) | 0.71748 (13) | 0.26867 (10) | 0.0737 (4) | |
Cl2 | 0.35804 (9) | 0.31378 (19) | 0.51508 (10) | 0.0737 (4) | |
O1 | 0.0420 (4) | 0.6234 (5) | 0.2882 (5) | 0.1136 (19) | |
O2 | 0.1006 (6) | 0.8427 (4) | 0.3105 (5) | 0.127 (2) | |
O3 | 0.1942 (5) | 0.6593 (8) | 0.3066 (8) | 0.175 (4) | |
O4A | 0.139 (2) | 0.708 (2) | 0.1798 (11) | 0.169 (11) | 0.50 |
O4B | 0.0776 (19) | 0.742 (3) | 0.1766 (10) | 0.174 (12) | 0.50 |
O5 | 0.4312 (5) | 0.3855 (14) | 0.5512 (6) | 0.206 (5) | |
O6A | 0.3918 (11) | 0.225 (2) | 0.5771 (16) | 0.193 (11) | 0.50 |
O7A | 0.3915 (15) | 0.283 (4) | 0.4304 (10) | 0.223 (13) | 0.50 |
O6B | 0.3283 (12) | 0.4259 (15) | 0.4624 (8) | 0.150 (6) | 0.50 |
O7B | 0.3506 (13) | 0.1892 (11) | 0.4775 (12) | 0.150 (7) | 0.50 |
O8 | 0.2781 (7) | 0.3232 (19) | 0.5483 (18) | 0.343 (12) | |
N1 | 0.2514 (3) | 0.0846 (4) | 0.2973 (3) | 0.0545 (9) | |
H1A | 0.2935 | 0.1166 | 0.3413 | 0.065* | |
H1B | 0.2146 | 0.0244 | 0.3225 | 0.065* | |
N2 | 0.2304 (3) | 0.1898 (4) | 0.1213 (2) | 0.0448 (8) | |
N3 | 0.0910 (3) | 0.3830 (4) | 0.1366 (2) | 0.0510 (8) | |
H3A | 0.0304 | 0.3622 | 0.1341 | 0.061* | |
H3B | 0.0981 | 0.4722 | 0.1524 | 0.061* | |
N4 | 0.2812 (3) | 0.3933 (5) | 0.2506 (3) | 0.0596 (11) | |
H4A | 0.2624 | 0.4769 | 0.2293 | 0.072* | |
H4B | 0.3019 | 0.4036 | 0.3102 | 0.072* | |
N5 | 0.0476 (2) | 0.1280 (3) | 0.2347 (2) | 0.0411 (7) | |
H5A | 0.0211 | 0.1174 | 0.1774 | 0.049* | |
H5B | 0.0625 | 0.0443 | 0.2580 | 0.049* | |
N6 | 0.1150 (2) | 0.3315 (3) | 0.3526 (2) | 0.0387 (7) | |
H6A | 0.1598 | 0.3300 | 0.3995 | 0.046* | |
H6B | 0.0982 | 0.4199 | 0.3426 | 0.046* | |
C1 | 0.2989 (3) | 0.0146 (5) | 0.2274 (4) | 0.0664 (13) | |
H1C | 0.3012 | −0.0837 | 0.2394 | 0.080* | |
H1D | 0.3619 | 0.0482 | 0.2294 | 0.080* | |
C2 | 0.2490 (4) | 0.0405 (5) | 0.1355 (4) | 0.0653 (13) | |
H2A | 0.2860 | 0.0070 | 0.0894 | 0.078* | |
H2B | 0.1909 | −0.0097 | 0.1294 | 0.078* | |
C3 | 0.1630 (4) | 0.2165 (6) | 0.0432 (3) | 0.0623 (12) | |
H3C | 0.1132 | 0.1498 | 0.0421 | 0.075* | |
H3D | 0.1925 | 0.2057 | −0.0120 | 0.075* | |
C4 | 0.1233 (4) | 0.3611 (5) | 0.0467 (3) | 0.0609 (12) | |
H4C | 0.1705 | 0.4284 | 0.0366 | 0.073* | |
H4D | 0.0722 | 0.3720 | −0.0004 | 0.073* | |
C5 | 0.3185 (5) | 0.2678 (6) | 0.1158 (5) | 0.0650 (19) | |
H5C | 0.3097 | 0.3318 | 0.0658 | 0.078* | |
H5D | 0.3669 | 0.2044 | 0.1045 | 0.078* | |
C6A | 0.3552 (5) | 0.3385 (10) | 0.2032 (6) | 0.070 (2) | 0.75 |
H6AC | 0.389 (5) | 0.275 (7) | 0.246 (6) | 0.084* | 0.75 |
H6AD | 0.393 (4) | 0.414 (6) | 0.186 (5) | 0.084* | 0.75 |
C6B | 0.3215 (15) | 0.4020 (16) | 0.1697 (13) | 0.059 (5) | 0.25 |
H6BC | 0.384 (3) | 0.437 (7) | 0.173 (4) | 0.071* | 0.25 |
H6BD | 0.282 (4) | 0.4493 | 0.122 (2) | 0.071* | 0.25 |
C7 | −0.0164 (3) | 0.1995 (6) | 0.2903 (3) | 0.0547 (11) | |
H7A | −0.0650 | 0.1364 | 0.3034 | 0.066* | |
H7B | −0.0451 | 0.2762 | 0.2561 | 0.066* | |
C8 | 0.0329 (5) | 0.2523 (4) | 0.3785 (5) | 0.0460 (13) | |
C9 | −0.0324 (4) | 0.3475 (6) | 0.4233 (4) | 0.0736 (15) | |
H9A | −0.0014 | 0.3828 | 0.4790 | 0.110* | |
H9B | −0.0863 | 0.2968 | 0.4360 | 0.110* | |
H9C | −0.0507 | 0.4226 | 0.3833 | 0.110* | |
C10 | 0.0679 (4) | 0.1353 (5) | 0.4431 (4) | 0.0682 (13) | |
H10A | 0.1101 | 0.0782 | 0.4143 | 0.102* | |
H10B | 0.0164 | 0.0809 | 0.4577 | 0.102* | |
H10C | 0.0991 | 0.1737 | 0.4978 | 0.102* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni | 0.03287 (19) | 0.03036 (18) | 0.03062 (18) | 0.00010 (17) | −0.00215 (13) | −0.00268 (17) |
Cl1 | 0.1205 (13) | 0.0400 (5) | 0.0610 (7) | −0.0118 (6) | 0.0114 (8) | −0.0055 (5) |
Cl2 | 0.0552 (6) | 0.0847 (10) | 0.0758 (9) | −0.0100 (6) | −0.0176 (6) | 0.0079 (7) |
O1 | 0.119 (4) | 0.060 (2) | 0.166 (6) | −0.017 (3) | 0.031 (4) | 0.016 (3) |
O2 | 0.200 (6) | 0.042 (2) | 0.133 (5) | 0.007 (3) | −0.008 (5) | −0.018 (3) |
O3 | 0.136 (6) | 0.111 (5) | 0.272 (12) | 0.052 (4) | −0.012 (6) | −0.029 (6) |
O4A | 0.28 (3) | 0.164 (15) | 0.076 (9) | −0.125 (19) | 0.062 (13) | −0.023 (10) |
O4B | 0.20 (3) | 0.27 (3) | 0.046 (7) | −0.012 (16) | 0.020 (11) | 0.016 (8) |
O5 | 0.119 (6) | 0.328 (15) | 0.153 (7) | −0.045 (7) | −0.060 (5) | −0.050 (9) |
O6A | 0.099 (10) | 0.27 (2) | 0.20 (2) | −0.001 (12) | −0.028 (12) | 0.160 (18) |
O7A | 0.126 (14) | 0.47 (4) | 0.069 (9) | 0.023 (17) | −0.022 (9) | −0.035 (15) |
O6B | 0.212 (16) | 0.141 (11) | 0.085 (8) | 0.070 (11) | −0.035 (9) | 0.013 (7) |
O7B | 0.226 (18) | 0.062 (6) | 0.143 (13) | −0.027 (8) | −0.072 (12) | −0.008 (7) |
O8 | 0.126 (8) | 0.291 (16) | 0.63 (4) | 0.021 (10) | 0.118 (15) | 0.03 (2) |
N1 | 0.051 (2) | 0.0495 (19) | 0.059 (2) | 0.0152 (16) | −0.0107 (17) | 0.0000 (17) |
N2 | 0.0496 (19) | 0.0417 (17) | 0.043 (2) | 0.0017 (15) | 0.0031 (16) | −0.0069 (14) |
N3 | 0.066 (2) | 0.0401 (17) | 0.0447 (19) | 0.0092 (15) | −0.0032 (17) | 0.0028 (14) |
N4 | 0.063 (2) | 0.060 (2) | 0.057 (2) | −0.0214 (19) | 0.0092 (19) | −0.0156 (18) |
N5 | 0.0403 (16) | 0.0373 (16) | 0.0437 (17) | −0.0082 (12) | −0.0039 (14) | −0.0076 (13) |
N6 | 0.0449 (17) | 0.0347 (15) | 0.0353 (17) | −0.0042 (13) | −0.0015 (13) | −0.0019 (12) |
C1 | 0.058 (3) | 0.048 (2) | 0.092 (4) | 0.024 (2) | 0.002 (2) | −0.006 (2) |
C2 | 0.079 (3) | 0.049 (2) | 0.069 (3) | 0.007 (2) | 0.016 (3) | −0.019 (2) |
C3 | 0.074 (3) | 0.072 (3) | 0.040 (2) | 0.000 (2) | 0.001 (2) | −0.012 (2) |
C4 | 0.073 (3) | 0.070 (3) | 0.039 (2) | −0.002 (2) | −0.003 (2) | 0.009 (2) |
C5 | 0.056 (4) | 0.075 (4) | 0.070 (5) | −0.002 (2) | 0.032 (3) | −0.008 (3) |
C6A | 0.049 (4) | 0.077 (5) | 0.085 (6) | −0.017 (3) | 0.012 (4) | −0.006 (4) |
C6B | 0.064 (12) | 0.062 (12) | 0.051 (11) | −0.028 (10) | 0.008 (9) | −0.002 (9) |
C7 | 0.043 (2) | 0.066 (3) | 0.054 (3) | −0.008 (2) | 0.0000 (19) | −0.005 (2) |
C8 | 0.051 (3) | 0.047 (3) | 0.040 (2) | −0.0048 (16) | 0.006 (2) | 0.0076 (15) |
C9 | 0.077 (3) | 0.084 (4) | 0.065 (3) | 0.001 (3) | 0.031 (3) | −0.015 (3) |
C10 | 0.088 (4) | 0.061 (3) | 0.055 (3) | −0.005 (2) | 0.004 (3) | 0.019 (2) |
Geometric parameters (Å, º) top
Ni—N6 | 2.092 (3) | N6—C8 | 1.502 (7) |
Ni—N4 | 2.110 (4) | N6—H6A | 0.9000 |
Ni—N2 | 2.118 (4) | N6—H6B | 0.9000 |
Ni—N5 | 2.145 (3) | C1—C2 | 1.495 (8) |
Ni—N3 | 2.166 (3) | C1—H1C | 0.9700 |
Ni—N1 | 2.176 (3) | C1—H1D | 0.9700 |
Cl1—O2 | 1.376 (5) | C2—H2A | 0.9700 |
Cl1—O1 | 1.389 (5) | C2—H2B | 0.9700 |
Cl1—O4B | 1.413 (14) | C3—C4 | 1.520 (7) |
Cl1—O3 | 1.419 (7) | C3—H3C | 0.9700 |
Cl1—O4A | 1.435 (13) | C3—H3D | 0.9700 |
Cl2—O8 | 1.312 (11) | C4—H4C | 0.9700 |
Cl2—O6A | 1.315 (11) | C4—H4D | 0.9700 |
Cl2—O7B | 1.331 (11) | C5—C6A | 1.512 (10) |
Cl2—O5 | 1.334 (7) | C5—C6B | 1.526 (13) |
Cl2—O6B | 1.382 (11) | C5—H5C | 0.970 |
Cl2—O7A | 1.425 (15) | C5—H5D | 0.960 |
N1—C1 | 1.471 (7) | C6A—H6AC | 0.98 (2) |
N1—H1A | 0.9000 | C6A—H6AD | 0.97 (2) |
N1—H1B | 0.9000 | C6B—H6BC | 0.965 (18) |
N2—C3 | 1.456 (6) | C6B—H6BD | 0.98 (2) |
N2—C2 | 1.485 (6) | C7—C8 | 1.511 (8) |
N2—C5 | 1.497 (8) | C7—H7A | 0.9700 |
N3—C4 | 1.475 (6) | C7—H7B | 0.9700 |
N3—H3A | 0.9000 | C8—C9 | 1.527 (9) |
N3—H3B | 0.9000 | C8—C10 | 1.537 (7) |
N4—C6B | 1.392 (18) | C9—H9A | 0.9600 |
N4—C6A | 1.448 (9) | C9—H9B | 0.9600 |
N4—H4A | 0.900 | C9—H9C | 0.9600 |
N4—H4B | 0.910 | C10—H10A | 0.9600 |
N5—C7 | 1.480 (6) | C10—H10B | 0.9600 |
N5—H5A | 0.9000 | C10—H10C | 0.9600 |
N5—H5B | 0.9000 | | |
| | | |
N6—Ni—N4 | 92.86 (15) | Ni—N6—H6B | 108.8 |
N6—Ni—N2 | 175.65 (15) | H6A—N6—H6B | 107.7 |
N4—Ni—N2 | 82.85 (16) | N1—C1—C2 | 110.2 (3) |
N6—Ni—N5 | 80.82 (13) | N1—C1—H1C | 109.6 |
N4—Ni—N5 | 173.51 (17) | C2—C1—H1C | 109.6 |
N2—Ni—N5 | 103.45 (14) | N1—C1—H1D | 109.6 |
N6—Ni—N3 | 98.36 (14) | C2—C1—H1D | 109.6 |
N4—Ni—N3 | 92.30 (17) | H1C—C1—H1D | 108.1 |
N2—Ni—N3 | 81.17 (15) | N2—C2—C1 | 110.9 (4) |
N5—Ni—N3 | 87.19 (15) | N2—C2—H2A | 109.5 |
N6—Ni—N1 | 100.04 (15) | C1—C2—H2A | 109.5 |
N4—Ni—N1 | 93.30 (18) | N2—C2—H2B | 109.5 |
N2—Ni—N1 | 80.97 (15) | C1—C2—H2B | 109.5 |
N5—Ni—N1 | 89.29 (14) | H2A—C2—H2B | 108.0 |
N3—Ni—N1 | 160.46 (14) | N2—C3—C4 | 111.2 (4) |
O2—Cl1—O1 | 112.8 (5) | N2—C3—H3C | 109.4 |
O2—Cl1—O4B | 104.6 (12) | C4—C3—H3C | 109.4 |
O1—Cl1—O4B | 98.6 (12) | N2—C3—H3D | 109.4 |
O2—Cl1—O3 | 106.8 (5) | C4—C3—H3D | 109.4 |
O1—Cl1—O3 | 104.9 (5) | H3C—C3—H3D | 108.0 |
O4B—Cl1—O3 | 128.9 (12) | N3—C4—C3 | 108.8 (4) |
O2—Cl1—O4A | 121.4 (10) | N3—C4—H4C | 109.9 |
O1—Cl1—O4A | 116.0 (8) | C3—C4—H4C | 109.9 |
O3—Cl1—O4A | 90.1 (14) | N3—C4—H4D | 109.9 |
O8—Cl2—O6A | 93.5 (14) | C3—C4—H4D | 109.9 |
O8—Cl2—O7B | 100.7 (13) | H4C—C4—H4D | 108.3 |
O8—Cl2—O5 | 120.8 (11) | N2—C5—C6A | 114.1 (5) |
O6A—Cl2—O5 | 80.8 (11) | N2—C5—C6B | 112.3 (8) |
O7B—Cl2—O5 | 131.9 (10) | N2—C5—H5C | 109.00 |
O8—Cl2—O6B | 85.5 (10) | C6A—C5—H5C | 111.8 (7) |
O7B—Cl2—O6B | 118.3 (9) | N2—C5—H5D | 109.00 |
O5—Cl2—O6B | 90.1 (9) | C6A—C5—H5D | 104.0 (7) |
O8—Cl2—O7A | 138.1 (14) | H5C—C5—H5D | 108.00 |
O6A—Cl2—O7A | 109.9 (17) | N4—C6A—C5 | 111.7 (6) |
O5—Cl2—O7A | 97.4 (12) | N4—C6A—H6AC | 105 (6) |
C1—N1—Ni | 110.1 (3) | C5—C6A—H6AC | 112 (6) |
C1—N1—H1A | 109.6 | N4—C6A—H6AD | 109 (5) |
Ni—N1—H1A | 109.6 | C5—C6A—H6AD | 106 (5) |
C1—N1—H1B | 109.6 | H6AC—C6A—H6AD | 113 (4) |
Ni—N1—H1B | 109.6 | N4—C6B—C5 | 114.1 (11) |
H1A—N1—H1B | 108.2 | N4—C6B—H6BC | 117 (3) |
C3—N2—C2 | 112.5 (4) | C5—C6B—H6BC | 108 (3) |
C3—N2—C5 | 111.9 (5) | N4—C6B—H6BD | 112 (4) |
C2—N2—C5 | 111.0 (4) | C5—C6B—H6BD | 92 (2) |
C3—N2—Ni | 106.6 (3) | H6BC—C6B—H6BD | 111 (4) |
C2—N2—Ni | 105.2 (3) | N5—C7—C8 | 111.9 (4) |
C5—N2—Ni | 109.4 (3) | N5—C7—H7A | 109.2 |
C4—N3—Ni | 110.2 (3) | C8—C7—H7A | 109.2 |
C4—N3—H3A | 109.6 | N5—C7—H7B | 109.2 |
Ni—N3—H3A | 109.6 | C8—C7—H7B | 109.2 |
C4—N3—H3B | 109.6 | H7A—C7—H7B | 107.9 |
Ni—N3—H3B | 109.6 | N6—C8—C7 | 105.6 (5) |
H3A—N3—H3B | 108.1 | N6—C8—C9 | 110.4 (4) |
C6B—N4—Ni | 110.5 (7) | C7—C8—C9 | 108.8 (5) |
C6A—N4—Ni | 109.2 (4) | N6—C8—C10 | 108.6 (5) |
C6A—N4—H4A | 112.0 (6) | C7—C8—C10 | 112.5 (4) |
Ni—N4—H4A | 110.00 | C9—C8—C10 | 110.8 (5) |
C6A—N4—H4B | 109.1 (5) | C8—C9—H9A | 109.5 |
Ni—N4—H4B | 110.00 | C8—C9—H9B | 109.5 |
H4A—N4—H4B | 107.00 | H9A—C9—H9B | 109.5 |
C7—N5—Ni | 106.6 (3) | C8—C9—H9C | 109.5 |
C7—N5—H5A | 110.4 | H9A—C9—H9C | 109.5 |
Ni—N5—H5A | 110.4 | H9B—C9—H9C | 109.5 |
C7—N5—H5B | 110.4 | C8—C10—H10A | 109.5 |
Ni—N5—H5B | 110.4 | C8—C10—H10B | 109.5 |
H5A—N5—H5B | 108.6 | H10A—C10—H10B | 109.5 |
C8—N6—Ni | 113.7 (3) | C8—C10—H10C | 109.5 |
C8—N6—H6A | 108.8 | H10A—C10—H10C | 109.5 |
Ni—N6—H6A | 108.8 | H10B—C10—H10C | 109.5 |
C8—N6—H6B | 108.8 | | |
| | | |
N6—Ni—N1—C1 | −178.8 (3) | Ni—N1—C1—C2 | −23.0 (5) |
N4—Ni—N1—C1 | −85.3 (3) | C3—N2—C2—C1 | −165.8 (4) |
N2—Ni—N1—C1 | −3.1 (3) | C5—N2—C2—C1 | 68.0 (6) |
N5—Ni—N1—C1 | 100.6 (3) | Ni—N2—C2—C1 | −50.2 (5) |
N3—Ni—N1—C1 | 21.1 (7) | N1—C1—C2—N2 | 49.8 (6) |
N4—Ni—N2—C3 | −117.9 (4) | C2—N2—C3—C4 | 162.5 (4) |
N5—Ni—N2—C3 | 60.5 (3) | C5—N2—C3—C4 | −71.8 (5) |
N3—Ni—N2—C3 | −24.4 (3) | Ni—N2—C3—C4 | 47.7 (5) |
N1—Ni—N2—C3 | 147.6 (3) | Ni—N3—C4—C3 | 27.1 (5) |
N4—Ni—N2—C2 | 122.5 (3) | N2—C3—C4—N3 | −50.9 (6) |
N5—Ni—N2—C2 | −59.1 (3) | C3—N2—C5—C6A | 134.5 (6) |
N3—Ni—N2—C2 | −144.1 (3) | C2—N2—C5—C6A | −99.0 (7) |
N1—Ni—N2—C2 | 28.0 (3) | Ni—N2—C5—C6A | 16.6 (7) |
N4—Ni—N2—C5 | 3.2 (4) | C3—N2—C5—C6B | 96.8 (11) |
N5—Ni—N2—C5 | −178.3 (3) | C2—N2—C5—C6B | −136.6 (11) |
N3—Ni—N2—C5 | 96.7 (4) | Ni—N2—C5—C6B | −21.0 (11) |
N1—Ni—N2—C5 | −91.3 (4) | Ni—N4—C6A—C6B | 98.9 (12) |
N6—Ni—N3—C4 | 173.7 (3) | C6B—N4—C6A—C5 | −60.8 (10) |
N4—Ni—N3—C4 | 80.4 (3) | Ni—N4—C6A—C5 | 38.1 (8) |
N2—Ni—N3—C4 | −2.0 (3) | N2—C5—C6A—C6B | −94.8 (14) |
N5—Ni—N3—C4 | −106.0 (3) | N2—C5—C6A—N4 | −37.2 (10) |
N1—Ni—N3—C4 | −26.1 (7) | C6B—C5—C6A—N4 | 57.7 (13) |
N6—Ni—N4—C6B | −162.8 (11) | C5—C6A—C6B—N4 | 122.3 (7) |
N2—Ni—N4—C6B | 16.5 (11) | N4—C6A—C6B—C5 | −122.3 (7) |
N3—Ni—N4—C6B | −64.3 (11) | Ni—N4—C6B—C6A | −94.9 (12) |
N1—Ni—N4—C6B | 97.0 (11) | C6A—N4—C6B—C5 | 61.7 (12) |
N6—Ni—N4—C6A | 157.8 (5) | Ni—N4—C6B—C5 | −33.2 (19) |
N2—Ni—N4—C6A | −22.9 (5) | N2—C5—C6B—C6A | 100.5 (14) |
N3—Ni—N4—C6A | −103.7 (5) | N2—C5—C6B—N4 | 37 (2) |
N1—Ni—N4—C6A | 57.6 (5) | C6A—C5—C6B—N4 | −63.4 (15) |
N6—Ni—N5—C7 | 20.0 (3) | Ni—N5—C7—C8 | −45.1 (5) |
N2—Ni—N5—C7 | −159.1 (3) | Ni—N6—C8—C7 | −31.5 (5) |
N3—Ni—N5—C7 | −78.9 (3) | Ni—N6—C8—C9 | −149.0 (4) |
N1—Ni—N5—C7 | 120.3 (3) | Ni—N6—C8—C10 | 89.4 (5) |
N4—Ni—N6—C8 | −174.6 (3) | N5—C7—C8—N6 | 50.8 (5) |
N5—Ni—N6—C8 | 6.9 (3) | N5—C7—C8—C9 | 169.3 (4) |
N3—Ni—N6—C8 | 92.6 (3) | N5—C7—C8—C10 | −67.5 (7) |
N1—Ni—N6—C8 | −80.8 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O7B | 0.90 | 2.21 | 3.069 (10) | 158 |
N1—H1A···O7A | 0.90 | 2.44 | 3.278 (10) | 159 |
N1—H1B···O2i | 0.90 | 2.41 | 3.232 (8) | 151 |
N3—H3A···O6Aii | 0.90 | 2.26 | 3.116 (10) | 158 |
N3—H3B···O4A | 0.90 | 2.39 | 3.281 (10) | 170 |
N4—H4A···O3 | 0.90 | 2.38 | 3.030 (9) | 129 |
N4—H4B···O6B | 0.91 | 2.26 | 3.156 (10) | 170 |
N4—H4B···O7A | 0.91 | 2.40 | 3.160 (10) | 139 |
N5—H5A···O5ii | 0.90 | 2.17 | 3.048 (9) | 167 |
N5—H5B···O2i | 0.90 | 2.16 | 3.056 (6) | 178 |
N6—H6A···O8 | 0.90 | 2.65 | 3.545 (15) | 174 |
N6—H6B···O1 | 0.90 | 2.25 | 3.138 (6) | 167 |
Symmetry codes: (i) x, y−1, z; (ii) x−1/2, −y+1/2, z−1/2. |