Tris­(phenanthroline-κ²N,N′)­nickel(II) di­bromo­succinate heptahydrate

The crystal structure of the title compound, [Ni(C₁₂H₈N₂)₃](C₄H₂Br₂O₄)·7H₂O, consists of discrete nickel(II) complex cations, di­bromo­succinate dianions and uncoordinated water mol­ecules. The Ni^II atom is surrounded by three phenanthroline ligands in a distorted octahedral geometry. The overlapped arrangement and short face-to-face distances of 3.525 (12) and 3.369 (5) Å between parallel phen planes of neighboring complexes indicate π–π stacking. The di­bromo­succinate dianions are located on inversion centers and are linked to uncoordinated water molecules via hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in solvent or counterion
• R factor = 0.052
• wR factor = 0.133
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      12.00 Perc.
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O71
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........        O72
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      74.00 A   3  

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Tris(phenanthroline-κ²N,N')nickel(II) dibromosuccinate pentahydrate

Crystal data

[Ni(C12H8N2)3](C4H2Br2O4)·7H2O	Z = 2
Mr = 999.27	F(000) = 1016
Triclinic, P1	Dx = 1.562 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 12.3571 (11) Å	Cell parameters from 9880 reflections
b = 12.6397 (12) Å	θ = 2.0–25.0°
c = 15.3369 (12) Å	µ = 2.40 mm^−1
α = 67.286 (3)°	T = 295 K
β = 89.668 (3)°	Prism, green
γ = 75.133 (2)°	0.52 × 0.48 × 0.43 mm
V = 2124.0 (3) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	7599 independent reflections
Radiation source: fine-focus sealed tube	5543 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.00 pixels mm^-1	θmax = 25.2°, θmin = 1.5°
ω scans	h = −14→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −15→15
Tmin = 0.286, Tmax = 0.352	l = −18→18
12401 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0562P)^2 + 4.025P] where P = (Fo^2 + 2Fc^2)/3
7599 reflections	(Δ/σ)max = 0.001
550 parameters	Δρmax = 1.09 e Å^−3
0 restraints	Δρmin = −1.39 e Å^−3

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. A PLATON analysis (Spek, 2003) showed there is a potential solvent accessible area of 74 (7) ų around (1/2, 0.0, 1/2), which implied one more independent lattice water molecule occurring in (I). A re-check of the difference Fourier map showed a smaller peak with electron density of 0.55 e.Å^-3 remaining at (0.519, 0.057, 0.484), which was temporarily assigned as a lattice water O8W atom. But the isotropic refinement for the O8W atom gave a smaller occupancy of 0.19 (3), which may indicate the unrealistic O8W. Thus the O8W atom was not included in the final 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)
Br1	0.53335 (6)	0.37305 (7)	0.42242 (6)	0.0921 (3)
Br2	0.88139 (5)	0.09434 (5)	1.08084 (4)	0.06140 (18)
Ni	0.19513 (5)	0.23261 (4)	0.29387 (4)	0.03347 (15)
N1	0.2156 (3)	0.1923 (3)	0.4414 (3)	0.0455 (9)
N2	0.1535 (3)	0.0714 (3)	0.3491 (3)	0.0429 (9)
N3	0.3613 (3)	0.1541 (3)	0.2671 (3)	0.0495 (10)
N4	0.2631 (3)	0.3777 (3)	0.2514 (3)	0.0434 (9)
N5	0.1326 (3)	0.2715 (3)	0.1481 (3)	0.0441 (9)
N6	0.0252 (3)	0.3446 (3)	0.2786 (3)	0.0422 (9)
O1	0.6822 (3)	0.5483 (3)	0.4425 (3)	0.0584 (9)
O2	0.7351 (3)	0.3941 (3)	0.5813 (3)	0.0650 (10)
O3	0.9013 (3)	0.1572 (3)	0.8442 (2)	0.0643 (10)
O4	0.7798 (3)	0.0499 (3)	0.8920 (2)	0.0645 (10)
O1W	0.4248 (3)	0.3062 (3)	0.7380 (3)	0.0721 (11)
H1A	0.4991	0.2689	0.7387	0.060*
H1B	0.4052	0.3501	0.6751	0.060*
O2W	0.2735 (3)	0.1773 (3)	0.8226 (3)	0.0686 (10)
H2A	0.2138	0.1735	0.8051	0.060*
H2B	0.3212	0.2068	0.7795	0.060*
O3W	0.6475 (3)	0.2121 (3)	0.7232 (3)	0.0631 (10)
H3A	0.6887	0.1749	0.7767	0.060*
H3B	0.6943	0.2226	0.6804	0.060*
O4W	0.9557 (3)	0.4137 (4)	0.5688 (3)	0.0935 (15)
H4A	0.8942	0.3985	0.5591	0.060*
H4B	0.9524	0.4835	0.5691	0.060*
O5W	1.0445 (3)	0.2913 (4)	0.7610 (3)	0.0762 (12)
H5A	0.9975	0.2384	0.7887	0.060*
H5B	1.0414	0.2992	0.7017	0.060*
O6W	0.4366 (4)	0.2825 (5)	0.9390 (4)	0.1069 (16)
H6A	0.4407	0.2845	0.8814	0.060*
H6B	0.5050	0.2403	0.9663	0.060*
O71	0.6098 (10)	0.0223 (12)	1.0108 (8)	0.102 (3)	0.50
O72	0.6188 (8)	−0.0547 (9)	1.0004 (7)	0.072 (2)	0.50
C1	0.2412 (5)	0.2548 (4)	0.4869 (4)	0.0591 (14)
H1	0.2609	0.3244	0.4517	0.071*
C2	0.2401 (5)	0.2217 (5)	0.5837 (4)	0.0691 (16)
H2	0.2557	0.2700	0.6120	0.083*
C3	0.2164 (5)	0.1187 (5)	0.6370 (4)	0.0620 (14)
H3	0.2151	0.0958	0.7023	0.074*
C4	0.1935 (4)	0.0464 (4)	0.5932 (3)	0.0492 (12)
C5	0.1715 (5)	−0.0665 (5)	0.6443 (4)	0.0647 (15)
H5	0.1736	−0.0957	0.7102	0.078*
C6	0.1479 (5)	−0.1304 (5)	0.5987 (4)	0.0627 (15)
H6	0.1360	−0.2043	0.6337	0.075*
C7	0.1405 (4)	−0.0879 (4)	0.4969 (3)	0.0471 (11)
C8	0.1126 (5)	−0.1495 (4)	0.4453 (4)	0.0581 (14)
H8	0.0993	−0.2236	0.4766	0.070*
C9	0.1052 (5)	−0.0994 (5)	0.3489 (4)	0.0580 (14)
H9	0.0865	−0.1389	0.3136	0.070*
C10	0.1256 (4)	0.0103 (4)	0.3033 (4)	0.0541 (13)
H10	0.1195	0.0431	0.2372	0.065*
C11	0.1609 (4)	0.0227 (4)	0.4455 (3)	0.0397 (10)
C12	0.1907 (4)	0.0893 (4)	0.4950 (3)	0.0408 (10)
C13	0.4082 (5)	0.0434 (5)	0.2736 (4)	0.0664 (15)
H13	0.3732	−0.0158	0.3052	0.080*
C14	0.5071 (6)	0.0136 (6)	0.2349 (5)	0.0805 (19)
H14	0.5371	−0.0643	0.2402	0.097*
C15	0.5599 (5)	0.0980 (6)	0.1893 (5)	0.0782 (18)
H15	0.6259	0.0784	0.1626	0.094*
C16	0.5156 (4)	0.2140 (5)	0.1824 (4)	0.0584 (13)
C17	0.5652 (5)	0.3091 (6)	0.1363 (5)	0.0793 (18)
H17	0.6318	0.2942	0.1090	0.095*
C18	0.5175 (5)	0.4205 (6)	0.1315 (5)	0.0759 (18)
H18	0.5524	0.4803	0.1017	0.091*
C19	0.4152 (4)	0.4477 (4)	0.1711 (4)	0.0506 (12)
C20	0.3623 (5)	0.5612 (5)	0.1691 (4)	0.0614 (14)
H20	0.3943	0.6237	0.1406	0.074*
C21	0.2650 (5)	0.5795 (5)	0.2083 (4)	0.0602 (14)
H21	0.2308	0.6539	0.2088	0.072*
C22	0.2158 (4)	0.4854 (4)	0.2484 (3)	0.0517 (12)
H22	0.1476	0.4994	0.2737	0.062*
C23	0.3627 (4)	0.3574 (4)	0.2151 (3)	0.0415 (10)
C24	0.4141 (4)	0.2390 (4)	0.2219 (3)	0.0432 (11)
C25	0.1858 (5)	0.2381 (4)	0.0838 (4)	0.0531 (13)
H25	0.2607	0.1933	0.0995	0.064*
C26	0.1348 (5)	0.2670 (5)	−0.0062 (4)	0.0580 (14)
H26	0.1756	0.2427	−0.0495	0.070*
C27	0.0250 (5)	0.3310 (4)	−0.0302 (4)	0.0547 (13)
H27	−0.0102	0.3503	−0.0899	0.066*
C28	−0.0345 (4)	0.3676 (4)	0.0357 (3)	0.0441 (11)
C29	−0.1496 (4)	0.4372 (5)	0.0156 (4)	0.0565 (13)
H29	−0.1882	0.4569	−0.0429	0.068*
C30	−0.2036 (4)	0.4750 (4)	0.0797 (4)	0.0546 (13)
H30	−0.2781	0.5212	0.0645	0.066*
C31	−0.1469 (4)	0.4445 (4)	0.1705 (3)	0.0466 (11)
C32	−0.1975 (5)	0.4829 (4)	0.2396 (4)	0.0570 (13)
H32	−0.2722	0.5285	0.2279	0.068*
C33	−0.1373 (5)	0.4535 (5)	0.3230 (4)	0.0604 (15)
H33	−0.1701	0.4792	0.3686	0.073*
C34	−0.0266 (5)	0.3851 (4)	0.3399 (4)	0.0527 (13)
H34	0.0137	0.3666	0.3974	0.063*
C35	−0.0341 (4)	0.3749 (4)	0.1932 (3)	0.0398 (10)
C36	0.0229 (4)	0.3365 (4)	0.1243 (3)	0.0371 (10)
C41	0.6653 (4)	0.4663 (4)	0.5133 (4)	0.0481 (11)
C42	0.5471 (4)	0.4464 (5)	0.5145 (4)	0.0591 (14)
H42	0.5393	0.3913	0.5784	0.071*
C43	0.8671 (4)	0.0775 (4)	0.9035 (3)	0.0432 (11)
C44	0.9378 (4)	0.0062 (4)	1.0001 (3)	0.0385 (10)
H44	0.9255	−0.0732	1.0281	0.046*
H7A	0.6644	−0.0071	0.9753	0.060*
H7B	0.5861	−0.0426	1.0445	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0707 (5)	0.1089 (6)	0.1342 (7)	−0.0163 (4)	0.0040 (4)	−0.0929 (5)
Br2	0.0636 (4)	0.0709 (4)	0.0631 (4)	−0.0166 (3)	0.0187 (3)	−0.0422 (3)
Ni	0.0381 (3)	0.0290 (3)	0.0361 (3)	−0.0125 (2)	0.0104 (2)	−0.0139 (2)
N1	0.048 (2)	0.036 (2)	0.053 (2)	−0.0168 (18)	0.0076 (18)	−0.0154 (18)
N2	0.043 (2)	0.044 (2)	0.042 (2)	−0.0123 (17)	0.0113 (17)	−0.0179 (17)
N3	0.049 (2)	0.045 (2)	0.054 (2)	−0.0137 (19)	0.0082 (19)	−0.0192 (19)
N4	0.042 (2)	0.043 (2)	0.045 (2)	−0.0077 (17)	0.0051 (18)	−0.0196 (17)
N5	0.052 (3)	0.037 (2)	0.048 (2)	−0.0157 (18)	0.0115 (19)	−0.0188 (17)
N6	0.048 (2)	0.044 (2)	0.038 (2)	−0.0203 (18)	0.0081 (17)	−0.0152 (17)
O1	0.045 (2)	0.060 (2)	0.066 (2)	−0.0238 (17)	0.0160 (17)	−0.0148 (18)
O2	0.038 (2)	0.072 (3)	0.070 (2)	−0.0115 (18)	−0.0045 (18)	−0.015 (2)
O3	0.065 (2)	0.056 (2)	0.050 (2)	−0.0201 (19)	0.0002 (18)	0.0039 (17)
O4	0.053 (2)	0.080 (3)	0.054 (2)	−0.027 (2)	−0.0068 (17)	−0.0144 (19)
O1W	0.056 (2)	0.077 (3)	0.063 (2)	−0.014 (2)	0.0169 (19)	−0.008 (2)
O2W	0.060 (2)	0.088 (3)	0.061 (2)	−0.028 (2)	0.0149 (19)	−0.028 (2)
O3W	0.047 (2)	0.065 (2)	0.058 (2)	−0.0105 (18)	−0.0033 (17)	−0.0082 (18)
O4W	0.061 (3)	0.110 (4)	0.102 (3)	−0.046 (3)	−0.001 (2)	−0.019 (3)
O5W	0.081 (3)	0.096 (3)	0.062 (2)	−0.048 (2)	0.017 (2)	−0.028 (2)
O6W	0.103 (4)	0.127 (4)	0.107 (4)	−0.037 (3)	0.004 (3)	−0.061 (3)
O71	0.093 (8)	0.124 (10)	0.074 (7)	−0.048 (8)	0.020 (5)	−0.013 (7)
O72	0.063 (5)	0.074 (6)	0.071 (6)	−0.026 (5)	0.021 (4)	−0.017 (5)
C1	0.067 (4)	0.045 (3)	0.068 (4)	−0.027 (3)	0.004 (3)	−0.018 (3)
C2	0.092 (5)	0.059 (3)	0.066 (4)	−0.028 (3)	−0.007 (3)	−0.031 (3)
C3	0.082 (4)	0.059 (3)	0.050 (3)	−0.023 (3)	−0.003 (3)	−0.025 (3)
C4	0.060 (3)	0.048 (3)	0.041 (3)	−0.017 (2)	0.005 (2)	−0.017 (2)
C5	0.098 (5)	0.054 (3)	0.042 (3)	−0.030 (3)	0.012 (3)	−0.015 (2)
C6	0.094 (4)	0.047 (3)	0.051 (3)	−0.034 (3)	0.017 (3)	−0.015 (2)
C7	0.057 (3)	0.043 (3)	0.045 (3)	−0.018 (2)	0.011 (2)	−0.019 (2)
C8	0.078 (4)	0.046 (3)	0.064 (3)	−0.029 (3)	0.022 (3)	−0.030 (3)
C9	0.071 (4)	0.058 (3)	0.063 (3)	−0.024 (3)	0.017 (3)	−0.039 (3)
C10	0.064 (3)	0.057 (3)	0.047 (3)	−0.018 (3)	0.014 (2)	−0.026 (2)
C11	0.041 (3)	0.039 (2)	0.040 (2)	−0.012 (2)	0.009 (2)	−0.0157 (19)
C12	0.037 (3)	0.038 (2)	0.047 (3)	−0.011 (2)	0.006 (2)	−0.016 (2)
C13	0.074 (4)	0.044 (3)	0.081 (4)	−0.017 (3)	0.010 (3)	−0.025 (3)
C14	0.076 (4)	0.055 (4)	0.108 (5)	−0.001 (3)	0.011 (4)	−0.041 (4)
C15	0.058 (4)	0.073 (4)	0.108 (5)	−0.011 (3)	0.028 (4)	−0.046 (4)
C16	0.044 (3)	0.060 (3)	0.072 (4)	−0.014 (3)	0.014 (3)	−0.028 (3)
C17	0.052 (4)	0.089 (5)	0.104 (5)	−0.026 (3)	0.036 (3)	−0.043 (4)
C18	0.058 (4)	0.077 (4)	0.098 (5)	−0.039 (3)	0.027 (3)	−0.028 (4)
C19	0.050 (3)	0.050 (3)	0.057 (3)	−0.024 (2)	0.006 (2)	−0.020 (2)
C20	0.070 (4)	0.052 (3)	0.068 (4)	−0.034 (3)	0.000 (3)	−0.019 (3)
C21	0.068 (4)	0.047 (3)	0.068 (4)	−0.013 (3)	−0.004 (3)	−0.027 (3)
C22	0.053 (3)	0.049 (3)	0.053 (3)	−0.008 (2)	0.004 (2)	−0.023 (2)
C23	0.038 (3)	0.045 (3)	0.043 (2)	−0.014 (2)	0.006 (2)	−0.017 (2)
C24	0.039 (3)	0.046 (3)	0.047 (3)	−0.017 (2)	0.007 (2)	−0.017 (2)
C25	0.056 (3)	0.045 (3)	0.063 (3)	−0.016 (2)	0.019 (3)	−0.025 (2)
C26	0.081 (4)	0.054 (3)	0.056 (3)	−0.030 (3)	0.026 (3)	−0.032 (3)
C27	0.075 (4)	0.055 (3)	0.046 (3)	−0.028 (3)	0.010 (3)	−0.026 (2)
C28	0.054 (3)	0.039 (2)	0.046 (3)	−0.023 (2)	0.007 (2)	−0.016 (2)
C29	0.055 (3)	0.065 (3)	0.054 (3)	−0.028 (3)	−0.003 (3)	−0.020 (3)
C30	0.039 (3)	0.052 (3)	0.066 (3)	−0.013 (2)	0.000 (2)	−0.015 (3)
C31	0.044 (3)	0.041 (3)	0.057 (3)	−0.018 (2)	0.013 (2)	−0.018 (2)
C32	0.049 (3)	0.048 (3)	0.076 (4)	−0.015 (2)	0.020 (3)	−0.026 (3)
C33	0.075 (4)	0.055 (3)	0.065 (4)	−0.028 (3)	0.035 (3)	−0.032 (3)
C34	0.071 (4)	0.050 (3)	0.048 (3)	−0.030 (3)	0.019 (3)	−0.023 (2)
C35	0.042 (3)	0.032 (2)	0.048 (3)	−0.018 (2)	0.012 (2)	−0.0152 (19)
C36	0.038 (3)	0.029 (2)	0.045 (2)	−0.0159 (19)	0.009 (2)	−0.0124 (18)
C41	0.036 (3)	0.049 (3)	0.054 (3)	−0.011 (2)	0.006 (2)	−0.016 (2)
C42	0.042 (3)	0.061 (3)	0.058 (3)	−0.015 (2)	0.006 (2)	−0.006 (3)
C43	0.047 (3)	0.045 (3)	0.035 (2)	−0.010 (2)	0.001 (2)	−0.015 (2)
C44	0.045 (3)	0.035 (2)	0.037 (2)	−0.011 (2)	0.005 (2)	−0.0151 (19)

Geometric parameters (Å, º)

Ni—N1	2.120 (4)	C7—C8	1.403 (7)
Ni—N2	2.082 (4)	C8—C9	1.358 (7)
Ni—N3	2.152 (4)	C8—H8	0.9300
Ni—N4	2.087 (4)	C9—C10	1.379 (7)
Ni—N5	2.195 (4)	C9—H9	0.9300
Ni—N6	2.165 (4)	C10—H10	0.9300
Br1—C42	1.994 (6)	C11—C12	1.442 (6)
Br2—C44	1.980 (4)	C13—C14	1.384 (8)
N1—C1	1.330 (6)	C13—H13	0.9300
N1—C12	1.357 (5)	C14—C15	1.352 (9)
N2—C10	1.329 (6)	C14—H14	0.9300
N2—C11	1.357 (5)	C15—C16	1.389 (8)
N3—C13	1.334 (6)	C15—H15	0.9300
N3—C24	1.355 (6)	C16—C24	1.406 (7)
N4—C22	1.319 (6)	C16—C17	1.427 (8)
N4—C23	1.353 (6)	C17—C18	1.352 (8)
N5—C25	1.324 (6)	C17—H17	0.9300
N5—C36	1.359 (6)	C18—C19	1.419 (8)
N6—C34	1.324 (6)	C18—H18	0.9300
N6—C35	1.370 (6)	C19—C23	1.400 (6)
O1—C41	1.239 (6)	C19—C20	1.404 (7)
O2—C41	1.240 (6)	C20—C21	1.348 (8)
O3—C43	1.236 (5)	C20—H20	0.9300
O4—C43	1.248 (6)	C21—C22	1.401 (7)
O1W—H1A	0.9167	C21—H21	0.9300
O1W—H1B	0.9031	C22—H22	0.9300
O2W—H2A	0.8053	C23—C24	1.430 (6)
O2W—H2B	0.9173	C25—C26	1.392 (7)
O3W—H3A	0.8598	C25—H25	0.9300
O3W—H3B	0.8663	C26—C27	1.357 (8)
O4W—H4A	0.8575	C26—H26	0.9300
O4W—H4B	0.8744	C27—C28	1.398 (7)
O5W—H5A	0.9700	C27—H27	0.9300
O5W—H5B	0.8742	C28—C36	1.400 (6)
O6W—H6A	0.8755	C28—C29	1.429 (7)
O6W—H6B	0.8808	C29—C30	1.353 (7)
O71—H7A	0.955	C29—H29	0.9300
O71—H7B	0.905	C30—C31	1.428 (7)
O72—H7A	0.906	C30—H30	0.9300
O72—H7B	0.830	C31—C35	1.406 (6)
C1—C2	1.378 (8)	C31—C32	1.408 (7)
C1—H1	0.9300	C32—C33	1.353 (8)
C2—C3	1.349 (7)	C32—H32	0.9300
C2—H2	0.9300	C33—C34	1.382 (8)
C3—C4	1.406 (7)	C33—H33	0.9300
C3—H3	0.9300	C34—H34	0.9300
C4—C12	1.387 (6)	C35—C36	1.436 (6)
C4—C5	1.434 (7)	C41—C42	1.543 (7)
C5—C6	1.337 (7)	C42—C42^i	1.457 (10)
C5—H5	0.9300	C42—H42	0.9800
C6—C7	1.436 (7)	C43—C44	1.532 (6)
C6—H6	0.9300	C44—C44^ii	1.505 (9)
C7—C11	1.402 (6)	C44—H44	0.9800
N2—Ni—N4	170.39 (15)	C14—C15—H15	120.0
N2—Ni—N1	79.46 (14)	C16—C15—H15	120.0
N4—Ni—N1	95.77 (14)	C15—C16—C24	117.4 (5)
N2—Ni—N3	94.04 (14)	C15—C16—C17	124.2 (5)
N4—Ni—N3	78.77 (14)	C24—C16—C17	118.4 (5)
N1—Ni—N3	102.63 (15)	C18—C17—C16	121.4 (5)
N2—Ni—N6	95.76 (14)	C18—C17—H17	119.3
N4—Ni—N6	92.72 (14)	C16—C17—H17	119.3
N1—Ni—N6	92.03 (14)	C17—C18—C19	121.2 (5)
N3—Ni—N6	163.64 (14)	C17—C18—H18	119.4
N2—Ni—N5	92.94 (14)	C19—C18—H18	119.4
N4—Ni—N5	93.34 (14)	C23—C19—C20	117.1 (5)
N1—Ni—N5	166.15 (14)	C23—C19—C18	119.1 (5)
N3—Ni—N5	89.34 (15)	C20—C19—C18	123.8 (5)
N6—Ni—N5	77.12 (14)	C21—C20—C19	120.0 (5)
C1—N1—C12	117.0 (4)	C21—C20—H20	120.0
C1—N1—Ni	130.3 (3)	C19—C20—H20	120.0
C12—N1—Ni	112.5 (3)	C20—C21—C22	119.4 (5)
C10—N2—C11	117.6 (4)	C20—C21—H21	120.3
C10—N2—Ni	128.9 (3)	C22—C21—H21	120.3
C11—N2—Ni	113.4 (3)	N4—C22—C21	122.2 (5)
C13—N3—C24	118.2 (4)	N4—C22—H22	118.9
C13—N3—Ni	129.7 (4)	C21—C22—H22	118.9
C24—N3—Ni	110.9 (3)	N4—C23—C19	122.4 (4)
C22—N4—C23	118.8 (4)	N4—C23—C24	117.8 (4)
C22—N4—Ni	127.6 (3)	C19—C23—C24	119.8 (4)
C23—N4—Ni	113.2 (3)	N3—C24—C16	122.3 (4)
C25—N5—C36	117.8 (4)	N3—C24—C23	117.6 (4)
C25—N5—Ni	129.0 (4)	C16—C24—C23	120.1 (4)
C36—N5—Ni	113.2 (3)	N5—C25—C26	123.1 (5)
C34—N6—C35	117.7 (4)	N5—C25—H25	118.4
C34—N6—Ni	128.8 (3)	C26—C25—H25	118.4
C35—N6—Ni	113.5 (3)	C27—C26—C25	119.5 (5)
H1A—O1W—H1B	101.3	C27—C26—H26	120.3
H2A—O2W—H2B	120.7	C25—C26—H26	120.3
H3A—O3W—H3B	105.3	C26—C27—C28	119.4 (5)
H4A—O4W—H4B	118.7	C26—C27—H27	120.3
H5A—O5W—H5B	102.7	C28—C27—H27	120.3
H6A—O6W—H6B	101.9	C27—C28—C36	117.8 (5)
H7A—O71—H7B	102.5	C27—C28—C29	123.0 (5)
H7A—O72—H7B	113.4	C36—C28—C29	119.1 (4)
N1—C1—C2	123.3 (5)	C30—C29—C28	121.5 (5)
N1—C1—H1	118.4	C30—C29—H29	119.2
C2—C1—H1	118.4	C28—C29—H29	119.2
C3—C2—C1	119.6 (5)	C29—C30—C31	120.5 (5)
C3—C2—H2	120.2	C29—C30—H30	119.8
C1—C2—H2	120.2	C31—C30—H30	119.8
C2—C3—C4	119.6 (5)	C35—C31—C32	117.1 (5)
C2—C3—H3	120.2	C35—C31—C30	119.6 (4)
C4—C3—H3	120.2	C32—C31—C30	123.3 (5)
C12—C4—C3	117.1 (4)	C33—C32—C31	119.9 (5)
C12—C4—C5	119.3 (4)	C33—C32—H32	120.1
C3—C4—C5	123.6 (5)	C31—C32—H32	120.1
C6—C5—C4	121.0 (5)	C32—C33—C34	119.6 (5)
C6—C5—H5	119.5	C32—C33—H33	120.2
C4—C5—H5	119.5	C34—C33—H33	120.2
C5—C6—C7	121.7 (5)	N6—C34—C33	123.5 (5)
C5—C6—H6	119.1	N6—C34—H34	118.3
C7—C6—H6	119.1	C33—C34—H34	118.3
C11—C7—C8	117.7 (4)	N6—C35—C31	122.2 (4)
C11—C7—C6	118.3 (4)	N6—C35—C36	118.2 (4)
C8—C7—C6	124.0 (4)	C31—C35—C36	119.6 (4)
C9—C8—C7	119.0 (5)	N5—C36—C28	122.4 (4)
C9—C8—H8	120.5	N5—C36—C35	117.8 (4)
C7—C8—H8	120.5	C28—C36—C35	119.7 (4)
C8—C9—C10	119.9 (5)	O2—C41—O1	126.9 (5)
C8—C9—H9	120.0	O2—C41—C42	116.1 (4)
C10—C9—H9	120.0	O1—C41—C42	116.9 (4)
N2—C10—C9	123.2 (5)	C42^i—C42—C41	115.7 (6)
N2—C10—H10	118.4	C42^i—C42—Br1	105.6 (5)
C9—C10—H10	118.4	C41—C42—Br1	108.1 (3)
N2—C11—C7	122.5 (4)	C42^i—C42—H42	109.1
N2—C11—C12	117.5 (4)	C41—C42—H42	109.1
C7—C11—C12	120.0 (4)	Br1—C42—H42	109.1
N1—C12—C4	123.3 (4)	O3—C43—O4	125.9 (4)
N1—C12—C11	117.0 (4)	O3—C43—C44	117.2 (4)
C4—C12—C11	119.7 (4)	O4—C43—C44	116.9 (4)
N3—C13—C14	122.2 (5)	C44^ii—C44—C43	116.1 (4)
N3—C13—H13	118.9	C44^ii—C44—Br2	106.5 (4)
C14—C13—H13	118.9	C43—C44—Br2	106.1 (3)
C15—C14—C13	119.9 (6)	C44^ii—C44—H44	109.3
C15—C14—H14	120.0	C43—C44—H44	109.3
C13—C14—H14	120.0	Br2—C44—H44	109.3
C14—C15—C16	120.0 (6)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O3W	0.92	1.84	2.750 (6)	172
O1W—H1B···O1^i	0.90	1.89	2.767 (6)	161
O2W—H2A···O5W^iii	0.81	2.17	2.804 (6)	136
O2W—H2B···O1W	0.92	1.95	2.781 (6)	149
O3W—H3A···O4	0.86	1.96	2.794 (5)	163
O3W—H3B···O2	0.87	2.30	2.930 (6)	130
O4W—H4A···O2	0.86	2.00	2.799 (6)	154
O4W—H4B···O4W^iv	0.87	2.46	2.838 (6)	107
O5W—H5A···O3	0.97	1.77	2.734 (6)	172
O5W—H5B···O4W	0.88	2.08	2.816 (6)	141
O6W—H6A···O1W	0.88	2.11	2.981 (7)	171
O6W—H6B···O71	0.88	2.54	3.198 (16)	132
O71—H7A···O4	0.96	1.99	2.774 (13)	137
O71—H7B···O71^v	0.91	2.49	2.955 (19)	113
O72—H7A···O4	0.91	2.00	2.844 (11)	155
O72—H7B···O72^v	0.83	2.48	2.904 (13)	113
C2—H2···O1^i	0.93	2.44	3.172 (8)	135
C9—H9···O3^vi	0.93	2.52	3.319 (7)	144
C21—H21···O3^i	0.93	2.35	3.223 (8)	155
C26—H26···O2W^vii	0.93	2.59	3.517 (7)	175
C33—H33···O1^iii	0.93	2.30	3.170 (7)	155
C42—H42···O3W	0.98	2.54	3.376 (7)	143

Symmetry codes: (i) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y, −z+2; (vi) −x+1, −y, −z+1; (vii) x, y, z−1.