(2-Methyl­propane-1,2-diamine-κ²N,N′)[tris­(2-amino­ethyl)amine-κ⁴N,N′,N′′,N′′′]nickel(II) diperchlorate

In the title compound, [N(C₄H₁₂N₂)(C₆H₁₈N₄)](ClO₄)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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](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

---

Computing details

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

Crystal data

[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) Å^3	Plate, light violet
Z = 4	0.25 × 0.20 × 0.08 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0953P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O2^i	0.90	2.41	3.232 (8)	151
N3—H3A···O6A^ii	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···O5^ii	0.90	2.17	3.048 (9)	167
N5—H5B···O2^i	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.