Disorder of the dimeric TCNQ–TCNQ unit in the crystal structure of [Ni(bpy)3]2(TCNQ–TCNQ)(TCNQ)2·6H2O (TCNQ is 7,7,8,8-tetra­cyano­quinodi­methane)

Černák, J.; Kuchár, J.; Hegedüs, M.

doi:10.1107/S2056989016019162

Disorder of the dimeric TCNQ–TCNQ unit in the crystal structure of [Ni(bpy)₃]₂(TCNQ–TCNQ)(TCNQ)₂·6H₂O (TCNQ is 7,7,8,8-tetracyanoquinodimethane)

The first example of an Ni^II complex containing an σ-dimerized TCNQ–TCNQ unit is presented, with a C—C bond length of 1.653 (11) Å. In addition, the σ-dimerized TCNQ–TCNQ unit (refined 75% occupancy) is disordered, forming also a less populated pair of TCNQ molecules (25% occupancy) with tightly π-stacked dicyanomethanide groups.

Keywords: crystal structure; nickel; 2,2′-bipyridine; σ-dimerized TCNQ–TCNQ dianion; disorder.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016019162/zl2686sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989016019162/zl2686Isup2.hkl Contains datablock I

CCDC reference: 1520298

checkCIF report

Key indicators

Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R factor = 0.049
wR factor = 0.126
Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflection(s) Below Theta(Min)          12 Note

Alert level C
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of         N8 Check
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  N3      ..       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  N5      ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  N12     ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20    ..  N2      ..       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H29    ..  N8      ..       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H29    ..  N11     ..       2.69 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C108 H76 N28 Ni2 O6
            Atom count from _chemical_formula_moiety:C126.0720 H82.02400 N34.024
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         36 Note
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records         10 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          7 Report
PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          8 Report
PLAT300_ALERT_4_G Atom Site Occupancy of *O1A    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H1A    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H1B    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *O1B    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H1C    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H1D    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *O3A    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H3A    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H3B    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *O3B    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H3C    is Constrained at        0.5 Check
PLAT300_ALERT_4_G Atom Site Occupancy of *H3D    is Constrained at        0.5 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..         56 % Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  5)..        100 % Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  6)..        100 % Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  7)..        100 % Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  8)..        100 % Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  9)..        100 % Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 10)..        100 % Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   1.50) in Resd. #          5 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   1.50) in Resd. #          6 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   2.72) in Resd. #          7 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   1.50) in Resd. #          8 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   1.50) in Resd. #          9 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms (   0.28) in Resd. #         10 Check
PLAT789_ALERT_4_G Atoms with Negative _atom_site_disorder_group  #          6 Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          7 Note
              H2 O
PLAT793_ALERT_4_G The Model has Chirality at C37A    (Centro SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         37 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600       1672 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   8 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  40 ALERT level G = General information/check it is not something unexpected

   3 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
  38 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: publCIF (Westrip, 2010).

Bis[tris(2,2'-bipyridine-κ²N,N')nickel(II)] bis(7,7,8,8-tetracyanoquinonedimethane radical anion) bi[7,7,8,8-tetracyanoquinonedimethanide] hexahydrate top

Crystal data top

[Ni(C₁₀H₈N₂)₃]₂(C₂₄H₈N₈)(C₁₂H₄N₄)₂·6H₂O	Z = 1
M_r = 1979.35	F(000) = 1024
Triclinic, P1	D_x = 1.345 Mg m⁻³
a = 12.4034 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.2921 (4) Å	Cell parameters from 10858 reflections
c = 15.4869 (4) Å	θ = 3.4–3.4°
α = 88.828 (3)°	µ = 0.46 mm⁻¹
β = 86.336 (3)°	T = 200 K
γ = 73.586 (3)°	Prism, green
V = 2444.21 (13) Å³	0.52 × 0.39 × 0.28 mm

Data collection top

Rigaku OD Xcalibur, Sapphire2, large Be window diffractometer	11255 independent reflections
Radiation source: fine-focus sealed X-ray tube	7475 reflections with I > 2σ(I)
Detector resolution: 8.3438 pixels mm^-1	R_int = 0.035
ω scans	θ_max = 29.0°, θ_min = 2.9°
Absorption correction: analytical [CrysAlis PRO (Rigaku OD, 2015), based on expressions derived by Clark & Reid (1995)]	h = −16→16
T_min = 0.864, T_max = 0.914	k = −18→17
31246 measured reflections	l = −20→19

Refinement top

Refinement on F²	37 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.050P)² + 0.5977P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
11255 reflections	Δρ_max = 0.34 e Å⁻³
726 parameters	Δρ_min = −0.24 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1A	0.1896 (5)	0.8735 (5)	0.8522 (4)	0.1007 (18)	0.5
H1A	0.247 (4)	0.847 (8)	0.820 (5)	0.151*	0.5
H1B	0.210 (7)	0.903 (5)	0.893 (2)	0.151*	0.5
O1B	0.0587 (5)	0.9770 (6)	0.9161 (4)	0.129 (2)	0.5
H1C	0.125 (4)	0.982 (9)	0.909 (3)	0.193*	0.5
H1D	0.033 (6)	1.005 (11)	0.964 (5)	0.193*	0.5
O2A	−0.1755 (2)	0.9694 (2)	0.65321 (18)	0.0834 (8)	0.908 (3)
H2A	−0.232 (2)	0.975 (3)	0.689 (2)	0.125*	0.908 (3)
H2B	−0.197 (3)	1.020 (2)	0.618 (2)	0.125*	0.908 (3)
O2B	−0.0574 (17)	1.0092 (17)	0.5847 (16)	0.0834 (8)	0.092 (3)
H2C	−0.1045	1.0697	0.5835	0.125*	0.092 (3)
H2D	−0.0210	1.0037	0.5357	0.125*	0.092 (3)
O3A	0.0233 (18)	0.8983 (17)	0.7290 (12)	0.186 (7)	0.5
H3A	−0.047 (2)	0.924 (13)	0.739 (2)	0.279*	0.5
H3B	0.051 (5)	0.911 (10)	0.775 (5)	0.279*	0.5
O3B	−0.0063 (16)	0.8831 (12)	0.7729 (13)	0.155 (7)	0.5
H3C	0.007 (9)	0.918 (8)	0.814 (7)	0.232*	0.5
H3D	−0.069 (5)	0.920 (10)	0.756 (3)	0.232*	0.5
Ni1	0.00252 (2)	0.36352 (2)	0.74798 (2)	0.03705 (10)
N1	−0.11257 (15)	0.28116 (15)	0.78825 (12)	0.0382 (4)
N2	0.02588 (16)	0.34809 (16)	0.88183 (12)	0.0415 (5)
N3	−0.01954 (16)	0.34866 (16)	0.61637 (12)	0.0399 (5)
N4	0.12404 (16)	0.22081 (16)	0.71749 (12)	0.0411 (5)
N5	−0.11165 (15)	0.51236 (16)	0.75713 (12)	0.0403 (5)
N6	0.10952 (16)	0.45865 (16)	0.73098 (12)	0.0418 (5)
C1	−0.11042 (19)	0.25284 (19)	0.87224 (15)	0.0392 (5)
C2	−0.1837 (2)	0.2005 (2)	0.90954 (17)	0.0535 (7)
H2	−0.1810	0.1814	0.9690	0.064*
C3	−0.2613 (2)	0.1765 (2)	0.85878 (19)	0.0582 (7)
H3	−0.3130	0.1416	0.8834	0.070*
C4	−0.2627 (2)	0.2036 (2)	0.77311 (18)	0.0519 (7)
H4	−0.3146	0.1872	0.7371	0.062*
C5	−0.1865 (2)	0.25578 (19)	0.74003 (17)	0.0445 (6)
H5	−0.1870	0.2742	0.6804	0.053*
C6	−0.0262 (2)	0.28306 (19)	0.92217 (15)	0.0403 (5)
C7	−0.0015 (2)	0.2457 (2)	1.00526 (16)	0.0583 (7)
H7	−0.0385	0.1988	1.0325	0.070*
C8	0.0777 (3)	0.2778 (3)	1.04744 (18)	0.0666 (9)
H8	0.0979	0.2513	1.1033	0.080*
C9	0.1271 (2)	0.3487 (3)	1.00788 (18)	0.0620 (8)
H9	0.1791	0.3743	1.0369	0.074*
C10	0.0994 (2)	0.3815 (2)	0.92542 (17)	0.0530 (7)
H10	0.1339	0.4301	0.8979	0.064*
C11	0.0359 (2)	0.25522 (19)	0.58218 (15)	0.0404 (5)
C12	0.0153 (3)	0.2252 (2)	0.50062 (17)	0.0587 (7)
H12	0.0555	0.1585	0.4776	0.070*
C13	−0.0648 (3)	0.2945 (3)	0.45379 (18)	0.0664 (9)
H13	−0.0827	0.2747	0.3991	0.080*
C14	−0.1182 (2)	0.3921 (3)	0.48679 (17)	0.0602 (8)
H14	−0.1711	0.4419	0.4543	0.072*
C15	−0.0937 (2)	0.4167 (2)	0.56792 (16)	0.0490 (6)
H15	−0.1306	0.4844	0.5906	0.059*
C16	0.1199 (2)	0.18548 (19)	0.63741 (16)	0.0414 (6)
C17	0.1909 (2)	0.0903 (2)	0.60849 (19)	0.0564 (7)
H17	0.1860	0.0656	0.5521	0.068*
C18	0.2686 (3)	0.0322 (2)	0.6630 (2)	0.0654 (8)
H18	0.3192	−0.0325	0.6438	0.078*
C19	0.2733 (2)	0.0672 (2)	0.7442 (2)	0.0627 (8)
H19	0.3263	0.0275	0.7824	0.075*
C20	0.1987 (2)	0.1624 (2)	0.76974 (18)	0.0530 (7)
H20	0.2008	0.1868	0.8266	0.064*
C21	−0.0658 (2)	0.59287 (19)	0.74590 (14)	0.0389 (5)
C22	−0.1307 (2)	0.6948 (2)	0.73577 (16)	0.0463 (6)
H22	−0.0963	0.7499	0.7271	0.056*
C23	−0.2465 (2)	0.7157 (2)	0.73844 (17)	0.0527 (7)
H23	−0.2927	0.7853	0.7311	0.063*
C24	−0.2941 (2)	0.6348 (2)	0.75180 (17)	0.0512 (7)
H24	−0.3735	0.6476	0.7552	0.061*
C25	−0.2239 (2)	0.5343 (2)	0.76024 (17)	0.0480 (6)
H25	−0.2569	0.4782	0.7686	0.058*
C26	0.0594 (2)	0.5614 (2)	0.74387 (14)	0.0399 (5)
C27	0.1211 (2)	0.6318 (2)	0.75518 (16)	0.0496 (6)
H27	0.0845	0.7038	0.7662	0.059*
C28	0.2382 (2)	0.5942 (3)	0.75003 (17)	0.0577 (8)
H28	0.2827	0.6406	0.7582	0.069*
C29	0.2888 (2)	0.4909 (3)	0.73328 (17)	0.0566 (7)
H29	0.3685	0.4648	0.7274	0.068*
C30	0.2221 (2)	0.4246 (2)	0.72501 (16)	0.0510 (7)
H30	0.2574	0.3522	0.7147	0.061*
N8	0.54409 (19)	0.48344 (18)	0.81067 (14)	0.0533 (6)
N9	0.3772 (3)	0.0161 (2)	1.21738 (16)	0.0813 (9)
N10	0.2633 (2)	0.0190 (2)	0.95837 (16)	0.0712 (8)
C34	0.42800 (19)	0.16964 (19)	1.03807 (14)	0.0385 (5)
N7A	0.7420 (5)	0.4375 (8)	1.0324 (8)	0.0541 (15)	0.753 (9)
C31A	0.5096 (4)	0.3468 (4)	0.9968 (3)	0.0344 (10)	0.753 (9)
C32A	0.5305 (7)	0.2926 (7)	1.0769 (5)	0.0389 (13)	0.753 (9)
H32A	0.5740	0.3147	1.1170	0.047*	0.753 (9)
C33A	0.4886 (9)	0.2079 (16)	1.0975 (10)	0.0393 (18)	0.753 (9)
H33A	0.5009	0.1752	1.1526	0.047*	0.753 (9)
C35A	0.4121 (11)	0.2223 (7)	0.9579 (4)	0.0415 (17)	0.753 (9)
H35A	0.3727	0.1977	0.9161	0.050*	0.753 (9)
C36A	0.4508 (6)	0.3076 (5)	0.9373 (5)	0.0389 (13)	0.753 (9)
H36A	0.4377	0.3402	0.8823	0.047*	0.753 (9)
C37A	0.5439 (3)	0.4471 (4)	0.9774 (2)	0.0368 (10)	0.753 (9)
C38A	0.6576 (2)	0.4385 (2)	1.00707 (16)	0.0434 (6)	0.753 (9)
C39A	0.5463 (7)	0.4688 (4)	0.8835 (3)	0.0334 (12)	0.753 (9)
N7B	0.725 (2)	0.460 (3)	1.041 (3)	0.0541 (15)	0.247 (9)
C31B	0.5328 (15)	0.3184 (15)	0.9834 (12)	0.0344 (10)	0.247 (9)
C32B	0.549 (3)	0.277 (3)	1.0618 (17)	0.0389 (13)	0.247 (9)
H32B	0.5941	0.3010	1.0993	0.047*	0.247 (9)
C33B	0.504 (3)	0.202 (5)	1.088 (3)	0.0393 (18)	0.247 (9)
H33B	0.5227	0.1687	1.1422	0.047*	0.247 (9)
C35B	0.423 (4)	0.203 (3)	0.9511 (13)	0.0415 (17)	0.247 (9)
H35B	0.3886	0.1719	0.9105	0.050*	0.247 (9)
C36B	0.470 (2)	0.2819 (19)	0.926 (2)	0.0389 (13)	0.247 (9)
H36B	0.4596	0.3116	0.8702	0.047*	0.247 (9)
C37B	0.5775 (11)	0.4002 (12)	0.9580 (8)	0.0368 (10)	0.247 (9)
C38B	0.6576 (2)	0.4385 (2)	1.00707 (16)	0.0434 (6)	0.247 (9)
C39B	0.561 (3)	0.4429 (15)	0.8746 (11)	0.0334 (12)	0.247 (9)
C40	0.3769 (2)	0.08793 (19)	1.06320 (15)	0.0437 (6)
C41	0.3786 (3)	0.0475 (2)	1.14731 (17)	0.0529 (7)
C42	0.3148 (2)	0.0497 (2)	1.00509 (16)	0.0481 (6)
N11	0.5248 (2)	0.7399 (2)	0.29382 (17)	0.0701 (7)
N12	0.7339 (2)	0.6518 (2)	0.51503 (18)	0.0747 (8)
C43	0.5416 (2)	0.8954 (2)	0.46974 (15)	0.0431 (6)
C44	0.5744 (2)	0.9267 (2)	0.54848 (16)	0.0477 (6)
H44	0.6255	0.8763	0.5817	0.057*
C45	0.4651 (2)	0.9737 (2)	0.42244 (16)	0.0475 (6)
H45	0.4412	0.9556	0.3693	0.057*
C46	0.5846 (2)	0.7918 (2)	0.43755 (17)	0.0479 (6)
C47	0.5512 (2)	0.7624 (2)	0.35862 (19)	0.0508 (6)
N13	0.7442 (2)	0.1592 (2)	0.54178 (17)	0.0708 (7)
N14	0.5887 (3)	0.2293 (2)	0.29481 (19)	0.0916 (10)
C48	0.6669 (2)	0.7136 (2)	0.48084 (18)	0.0531 (7)
C49	0.5579 (2)	0.3964 (2)	0.47270 (16)	0.0490 (7)
C50	0.5688 (2)	0.4322 (2)	0.55632 (16)	0.0523 (7)
H50	0.6156	0.3859	0.5950	0.063*
C51	0.4861 (2)	0.4685 (2)	0.41768 (16)	0.0518 (7)
H51	0.4763	0.4468	0.3614	0.062*
C52	0.6141 (2)	0.2929 (2)	0.44541 (17)	0.0539 (7)
C53	0.6858 (2)	0.2194 (2)	0.49858 (18)	0.0549 (7)
C54	0.6000 (3)	0.2571 (2)	0.3622 (2)	0.0646 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.135 (5)	0.103 (4)	0.097 (4)	−0.076 (4)	−0.062 (3)	0.024 (3)
O1B	0.111 (5)	0.151 (6)	0.161 (6)	−0.089 (5)	−0.067 (4)	0.062 (5)
O2A	0.095 (2)	0.0602 (16)	0.086 (2)	−0.0038 (15)	−0.0259 (15)	0.0048 (14)
O2B	0.095 (2)	0.0602 (16)	0.086 (2)	−0.0038 (15)	−0.0259 (15)	0.0048 (14)
O3A	0.167 (11)	0.162 (14)	0.248 (18)	−0.060 (9)	−0.114 (12)	0.053 (10)
O3B	0.159 (12)	0.082 (5)	0.250 (17)	−0.054 (6)	−0.131 (12)	0.071 (8)
Ni1	0.03132 (16)	0.04012 (19)	0.03937 (17)	−0.00905 (13)	−0.00397 (12)	−0.00099 (13)
N1	0.0336 (10)	0.0374 (11)	0.0430 (11)	−0.0081 (9)	−0.0075 (8)	−0.0009 (9)
N2	0.0373 (11)	0.0474 (12)	0.0413 (11)	−0.0134 (10)	−0.0060 (9)	−0.0056 (9)
N3	0.0379 (11)	0.0399 (12)	0.0394 (11)	−0.0066 (9)	−0.0059 (9)	0.0054 (9)
N4	0.0360 (11)	0.0432 (12)	0.0420 (11)	−0.0071 (9)	−0.0057 (9)	0.0030 (9)
N5	0.0311 (10)	0.0421 (12)	0.0478 (11)	−0.0109 (9)	0.0004 (9)	−0.0019 (9)
N6	0.0325 (10)	0.0486 (13)	0.0442 (11)	−0.0111 (10)	−0.0015 (9)	−0.0020 (9)
C1	0.0398 (13)	0.0367 (13)	0.0412 (13)	−0.0106 (11)	−0.0025 (10)	−0.0031 (10)
C2	0.0614 (17)	0.0563 (17)	0.0477 (15)	−0.0254 (15)	−0.0009 (13)	0.0012 (13)
C3	0.0547 (17)	0.0537 (17)	0.074 (2)	−0.0296 (15)	0.0025 (15)	0.0002 (15)
C4	0.0458 (15)	0.0441 (15)	0.0702 (18)	−0.0172 (13)	−0.0140 (13)	−0.0056 (13)
C5	0.0413 (14)	0.0438 (15)	0.0502 (14)	−0.0127 (12)	−0.0132 (11)	0.0006 (12)
C6	0.0389 (13)	0.0442 (14)	0.0367 (12)	−0.0095 (11)	−0.0019 (10)	−0.0055 (11)
C7	0.0668 (19)	0.073 (2)	0.0397 (14)	−0.0265 (16)	−0.0074 (13)	0.0007 (14)
C8	0.073 (2)	0.090 (2)	0.0379 (15)	−0.0221 (19)	−0.0156 (14)	−0.0043 (15)
C9	0.0554 (17)	0.087 (2)	0.0486 (16)	−0.0246 (17)	−0.0145 (14)	−0.0170 (15)
C10	0.0467 (15)	0.0690 (19)	0.0499 (15)	−0.0250 (14)	−0.0078 (12)	−0.0104 (14)
C11	0.0396 (13)	0.0432 (14)	0.0385 (12)	−0.0127 (12)	−0.0004 (10)	0.0023 (11)
C12	0.0697 (19)	0.0617 (19)	0.0438 (15)	−0.0160 (16)	−0.0050 (14)	−0.0070 (13)
C13	0.082 (2)	0.081 (2)	0.0377 (15)	−0.0225 (19)	−0.0177 (15)	0.0044 (15)
C14	0.0613 (18)	0.073 (2)	0.0451 (15)	−0.0142 (16)	−0.0168 (14)	0.0167 (15)
C15	0.0464 (14)	0.0493 (16)	0.0472 (14)	−0.0067 (13)	−0.0068 (12)	0.0086 (12)
C16	0.0381 (13)	0.0383 (14)	0.0460 (14)	−0.0092 (11)	0.0013 (11)	0.0016 (11)
C17	0.0571 (17)	0.0441 (16)	0.0621 (17)	−0.0053 (14)	0.0000 (14)	−0.0055 (13)
C18	0.0598 (19)	0.0400 (16)	0.083 (2)	0.0053 (14)	0.0029 (16)	0.0020 (15)
C19	0.0479 (16)	0.0545 (18)	0.074 (2)	0.0051 (14)	−0.0104 (15)	0.0178 (16)
C20	0.0439 (15)	0.0562 (18)	0.0529 (16)	−0.0033 (13)	−0.0116 (12)	0.0077 (13)
C21	0.0419 (13)	0.0415 (14)	0.0347 (12)	−0.0136 (12)	−0.0043 (10)	−0.0030 (10)
C22	0.0517 (16)	0.0424 (15)	0.0461 (14)	−0.0146 (13)	−0.0067 (12)	−0.0015 (11)
C23	0.0541 (16)	0.0423 (15)	0.0554 (16)	−0.0025 (13)	−0.0069 (13)	−0.0034 (12)
C24	0.0361 (14)	0.0530 (17)	0.0594 (16)	−0.0039 (13)	−0.0010 (12)	−0.0085 (13)
C25	0.0361 (13)	0.0460 (15)	0.0621 (16)	−0.0125 (12)	0.0006 (12)	−0.0038 (13)
C26	0.0405 (13)	0.0481 (15)	0.0342 (12)	−0.0171 (12)	−0.0041 (10)	0.0013 (11)
C27	0.0553 (16)	0.0537 (17)	0.0463 (14)	−0.0250 (14)	−0.0084 (12)	−0.0002 (12)
C28	0.0534 (17)	0.080 (2)	0.0530 (16)	−0.0391 (17)	−0.0104 (13)	0.0025 (15)
C29	0.0388 (14)	0.080 (2)	0.0559 (16)	−0.0245 (15)	−0.0060 (12)	0.0024 (15)
C30	0.0358 (14)	0.0642 (18)	0.0539 (16)	−0.0157 (13)	−0.0006 (12)	−0.0021 (13)
N8	0.0599 (14)	0.0644 (16)	0.0454 (13)	−0.0334 (13)	−0.0035 (11)	0.0019 (11)
N9	0.142 (3)	0.0666 (18)	0.0517 (15)	−0.0527 (19)	−0.0295 (16)	0.0160 (13)
N10	0.092 (2)	0.0799 (19)	0.0594 (15)	−0.0493 (17)	−0.0246 (14)	0.0083 (13)
C34	0.0394 (13)	0.0392 (13)	0.0367 (12)	−0.0101 (11)	−0.0057 (10)	−0.0006 (10)
N7A	0.038 (3)	0.055 (5)	0.069 (3)	−0.011 (3)	−0.007 (3)	−0.014 (3)
C31A	0.033 (3)	0.035 (3)	0.036 (2)	−0.012 (2)	−0.0042 (18)	−0.0033 (17)
C32A	0.039 (4)	0.050 (4)	0.030 (3)	−0.013 (3)	−0.008 (2)	−0.005 (2)
C33A	0.045 (4)	0.042 (3)	0.032 (4)	−0.012 (4)	−0.009 (3)	0.001 (2)
C35A	0.046 (3)	0.047 (4)	0.0359 (16)	−0.020 (3)	−0.0114 (18)	−0.001 (2)
C36A	0.041 (3)	0.049 (4)	0.029 (3)	−0.017 (3)	−0.006 (2)	0.001 (2)
C37A	0.035 (2)	0.043 (3)	0.0364 (19)	−0.016 (2)	−0.0047 (16)	−0.0032 (17)
C38A	0.0355 (13)	0.0482 (15)	0.0483 (14)	−0.0143 (12)	−0.0043 (11)	−0.0031 (12)
C39A	0.031 (3)	0.030 (3)	0.0401 (17)	−0.011 (3)	0.0026 (17)	−0.0086 (18)
N7B	0.038 (3)	0.055 (5)	0.069 (3)	−0.011 (3)	−0.007 (3)	−0.014 (3)
C31B	0.033 (3)	0.035 (3)	0.036 (2)	−0.012 (2)	−0.0042 (18)	−0.0033 (17)
C32B	0.039 (4)	0.050 (4)	0.030 (3)	−0.013 (3)	−0.008 (2)	−0.005 (2)
C33B	0.045 (4)	0.042 (3)	0.032 (4)	−0.012 (4)	−0.009 (3)	0.001 (2)
C35B	0.046 (3)	0.047 (4)	0.0359 (16)	−0.020 (3)	−0.0114 (18)	−0.001 (2)
C36B	0.041 (3)	0.049 (4)	0.029 (3)	−0.017 (3)	−0.006 (2)	0.001 (2)
C37B	0.035 (2)	0.043 (3)	0.0364 (19)	−0.016 (2)	−0.0047 (16)	−0.0032 (17)
C38B	0.0355 (13)	0.0482 (15)	0.0483 (14)	−0.0143 (12)	−0.0043 (11)	−0.0031 (12)
C39B	0.031 (3)	0.030 (3)	0.0401 (17)	−0.011 (3)	0.0026 (17)	−0.0086 (18)
C40	0.0560 (15)	0.0388 (14)	0.0390 (13)	−0.0161 (12)	−0.0122 (11)	0.0017 (11)
C41	0.079 (2)	0.0384 (15)	0.0488 (16)	−0.0259 (14)	−0.0176 (14)	0.0023 (12)
C42	0.0624 (17)	0.0473 (15)	0.0413 (13)	−0.0254 (14)	−0.0096 (12)	0.0059 (12)
N11	0.0596 (16)	0.0695 (18)	0.0756 (18)	−0.0043 (13)	−0.0215 (14)	−0.0143 (14)
N12	0.0734 (18)	0.0589 (17)	0.0824 (19)	0.0006 (14)	−0.0258 (15)	0.0092 (14)
C43	0.0384 (13)	0.0483 (15)	0.0435 (13)	−0.0131 (12)	−0.0070 (11)	0.0088 (11)
C44	0.0456 (14)	0.0496 (16)	0.0467 (14)	−0.0094 (13)	−0.0167 (12)	0.0129 (12)
C45	0.0442 (14)	0.0572 (17)	0.0409 (13)	−0.0121 (13)	−0.0133 (11)	0.0056 (12)
C46	0.0456 (14)	0.0464 (16)	0.0523 (15)	−0.0122 (13)	−0.0130 (12)	0.0081 (12)
C47	0.0385 (14)	0.0469 (16)	0.0645 (17)	−0.0058 (12)	−0.0121 (13)	0.0001 (13)
N13	0.0707 (17)	0.0765 (19)	0.0655 (16)	−0.0187 (15)	−0.0198 (14)	0.0149 (14)
N14	0.143 (3)	0.0602 (18)	0.0742 (19)	−0.0231 (18)	−0.0528 (19)	0.0038 (15)
C48	0.0482 (16)	0.0474 (16)	0.0648 (17)	−0.0135 (14)	−0.0119 (14)	0.0019 (14)
C49	0.0516 (15)	0.0598 (18)	0.0451 (14)	−0.0300 (14)	−0.0131 (12)	0.0167 (13)
C50	0.0590 (17)	0.0601 (18)	0.0457 (15)	−0.0269 (15)	−0.0214 (13)	0.0201 (13)
C51	0.0613 (17)	0.0618 (19)	0.0408 (14)	−0.0287 (15)	−0.0180 (13)	0.0142 (13)
C52	0.0638 (18)	0.0572 (18)	0.0501 (15)	−0.0298 (15)	−0.0199 (13)	0.0161 (13)
C53	0.0595 (17)	0.0591 (18)	0.0515 (16)	−0.0238 (15)	−0.0156 (14)	0.0126 (14)
C54	0.090 (2)	0.0494 (17)	0.0608 (18)	−0.0253 (17)	−0.0302 (17)	0.0153 (14)

Geometric parameters (Å, º) top

O1A—H1A	0.844 (10)	C24—C25	1.382 (4)
O1A—H1B	0.837 (10)	C24—H24	0.9500
O1B—H1C	0.844 (10)	C25—H25	0.9500
O1B—H1D	0.845 (10)	C26—C27	1.385 (3)
O2A—H2A	0.852 (10)	C27—C28	1.394 (4)
O2A—H2B	0.850 (10)	C27—H27	0.9500
O2B—H2C	0.8508	C28—C29	1.362 (4)
O2B—H2D	0.8509	C28—H28	0.9500
O3A—H3A	0.853 (10)	C29—C30	1.381 (4)
O3A—H3B	0.853 (10)	C29—H29	0.9500
O3B—H3C	0.853 (10)	C30—H30	0.9500
O3B—H3D	0.853 (10)	N8—C39B	1.121 (15)
Ni1—N6	2.078 (2)	N8—C39A	1.142 (5)
Ni1—N5	2.084 (2)	N9—C41	1.155 (3)
Ni1—N1	2.0897 (19)	N10—C42	1.147 (3)
Ni1—N3	2.0945 (19)	C34—C35B	1.409 (16)
Ni1—N4	2.103 (2)	C34—C35A	1.410 (6)
Ni1—N2	2.1093 (19)	C34—C33A	1.412 (6)
N1—C5	1.336 (3)	C34—C33B	1.416 (16)
N1—C1	1.346 (3)	C34—C40	1.440 (3)
N2—C6	1.340 (3)	N7A—C38A	1.137 (5)
N2—C10	1.343 (3)	C31A—C36A	1.405 (9)
N3—C11	1.339 (3)	C31A—C32A	1.422 (8)
N3—C15	1.348 (3)	C31A—C37A	1.527 (7)
N4—C20	1.334 (3)	C32A—C33A	1.39 (2)
N4—C16	1.344 (3)	C32A—H32A	0.9500
N5—C25	1.338 (3)	C33A—H33A	0.9500
N5—C21	1.350 (3)	C35A—C36A	1.375 (6)
N6—C30	1.338 (3)	C35A—H35A	0.9500
N6—C26	1.344 (3)	C36A—H36A	0.9500
C1—C2	1.385 (3)	C37A—C39A	1.477 (6)
C1—C6	1.484 (3)	C37A—C38A	1.485 (4)
C2—C3	1.388 (4)	C37A—C37Aⁱ	1.653 (11)
C2—H2	0.9500	N7B—C38B	1.123 (15)
C3—C4	1.367 (4)	C31B—C32B	1.33 (2)
C3—H3	0.9500	C31B—C37B	1.39 (3)
C4—C5	1.390 (4)	C31B—C36B	1.39 (3)
C4—H4	0.9500	C32B—C33B	1.32 (8)
C5—H5	0.9500	C32B—H32B	0.9500
C6—C7	1.391 (3)	C33B—H33B	0.9500
C7—C8	1.380 (4)	C35B—C36B	1.368 (16)
C7—H7	0.9500	C35B—H35B	0.9500
C8—C9	1.375 (4)	C36B—H36B	0.9500
C8—H8	0.9500	C37B—C39B	1.404 (19)
C9—C10	1.374 (4)	C37B—C38B	1.490 (11)
C9—H9	0.9500	C40—C41	1.398 (3)
C10—H10	0.9500	C40—C42	1.411 (3)
C11—C12	1.392 (3)	N11—C47	1.146 (3)
C11—C16	1.487 (3)	N12—C48	1.140 (3)
C12—C13	1.382 (4)	C43—C44	1.416 (3)
C12—H12	0.9500	C43—C46	1.418 (4)
C13—C14	1.372 (4)	C43—C45	1.421 (3)
C13—H13	0.9500	C44—C45ⁱⁱ	1.352 (4)
C14—C15	1.378 (4)	C44—H44	0.9500
C14—H14	0.9500	C45—C44ⁱⁱ	1.352 (4)
C15—H15	0.9500	C45—H45	0.9500
C16—C17	1.386 (4)	C46—C47	1.412 (4)
C17—C18	1.377 (4)	C46—C48	1.424 (4)
C17—H17	0.9500	N13—C53	1.151 (3)
C18—C19	1.360 (4)	N14—C54	1.143 (4)
C18—H18	0.9500	C49—C52	1.415 (4)
C19—C20	1.388 (4)	C49—C50	1.417 (4)
C19—H19	0.9500	C49—C51	1.421 (3)
C20—H20	0.9500	C50—C51ⁱⁱⁱ	1.359 (4)
C21—C22	1.378 (3)	C50—H50	0.9500
C21—C26	1.488 (3)	C51—C50ⁱⁱⁱ	1.359 (4)
C22—C23	1.382 (4)	C51—H51	0.9500
C22—H22	0.9500	C52—C53	1.412 (4)
C23—C24	1.371 (4)	C52—C54	1.422 (4)
C23—H23	0.9500

H1A—O1A—H1B	106.7 (17)	C24—C23—H23	120.3
H1C—O1B—H1D	105.8 (17)	C22—C23—H23	120.3
H2A—O2A—H2B	104.4 (16)	C23—C24—C25	118.6 (2)
H2C—O2B—H2D	104.3	C23—C24—H24	120.7
H3A—O3A—H3B	103.5 (17)	C25—C24—H24	120.7
H3C—O3B—H3D	103.8 (17)	N5—C25—C24	123.0 (2)
N6—Ni1—N5	78.69 (8)	N5—C25—H25	118.5
N6—Ni1—N1	169.09 (7)	C24—C25—H25	118.5
N5—Ni1—N1	96.11 (7)	N6—C26—C27	121.8 (2)
N6—Ni1—N3	96.17 (8)	N6—C26—C21	115.2 (2)
N5—Ni1—N3	93.51 (8)	C27—C26—C21	123.1 (2)
N1—Ni1—N3	93.69 (7)	C26—C27—C28	118.3 (3)
N6—Ni1—N4	96.76 (8)	C26—C27—H27	120.8
N5—Ni1—N4	170.39 (7)	C28—C27—H27	120.8
N1—Ni1—N4	89.75 (8)	C29—C28—C27	119.7 (3)
N3—Ni1—N4	78.47 (7)	C29—C28—H28	120.1
N6—Ni1—N2	92.20 (8)	C27—C28—H28	120.1
N5—Ni1—N2	94.96 (8)	C28—C29—C30	118.8 (3)
N1—Ni1—N2	78.61 (7)	C28—C29—H29	120.6
N3—Ni1—N2	169.11 (8)	C30—C29—H29	120.6
N4—Ni1—N2	93.66 (8)	N6—C30—C29	122.4 (3)
C5—N1—C1	118.4 (2)	N6—C30—H30	118.8
C5—N1—Ni1	126.90 (17)	C29—C30—H30	118.8
C1—N1—Ni1	114.74 (14)	C35A—C34—C33A	116.5 (11)
C6—N2—C10	118.3 (2)	C35B—C34—C33B	116 (3)
C6—N2—Ni1	113.74 (14)	C35B—C34—C40	117.9 (15)
C10—N2—Ni1	127.01 (18)	C35A—C34—C40	123.0 (5)
C11—N3—C15	118.2 (2)	C33A—C34—C40	120.3 (9)
C11—N3—Ni1	114.60 (15)	C33B—C34—C40	124 (3)
C15—N3—Ni1	126.56 (17)	C36A—C31A—C32A	117.3 (7)
C20—N4—C16	118.7 (2)	C36A—C31A—C37A	120.8 (5)
C20—N4—Ni1	126.95 (18)	C32A—C31A—C37A	121.8 (6)
C16—N4—Ni1	114.24 (15)	C33A—C32A—C31A	121.3 (9)
C25—N5—C21	117.9 (2)	C33A—C32A—H32A	119.4
C25—N5—Ni1	126.20 (17)	C31A—C32A—H32A	119.4
C21—N5—Ni1	115.10 (15)	C32A—C33A—C34	121.1 (15)
C30—N6—C26	118.9 (2)	C32A—C33A—H33A	119.4
C30—N6—Ni1	125.19 (18)	C34—C33A—H33A	119.4
C26—N6—Ni1	114.65 (15)	C36A—C35A—C34	123.1 (9)
N1—C1—C2	121.8 (2)	C36A—C35A—H35A	118.5
N1—C1—C6	115.7 (2)	C34—C35A—H35A	118.5
C2—C1—C6	122.5 (2)	C35A—C36A—C31A	120.6 (9)
C1—C2—C3	119.0 (2)	C35A—C36A—H36A	119.7
C1—C2—H2	120.5	C31A—C36A—H36A	119.7
C3—C2—H2	120.5	C39A—C37A—C38A	107.7 (4)
C4—C3—C2	119.5 (3)	C39A—C37A—C31A	110.8 (4)
C4—C3—H3	120.3	C38A—C37A—C31A	111.4 (3)
C2—C3—H3	120.3	C39A—C37A—C37Aⁱ	105.6 (4)
C3—C4—C5	118.4 (2)	C38A—C37A—C37Aⁱ	107.4 (3)
C3—C4—H4	120.8	C31A—C37A—C37Aⁱ	113.6 (3)
C5—C4—H4	120.8	N7A—C38A—C37A	175.9 (4)
N1—C5—C4	123.0 (2)	N8—C39A—C37A	176.7 (8)
N1—C5—H5	118.5	C32B—C31B—C37B	120 (2)
C4—C5—H5	118.5	C32B—C31B—C36B	121 (3)
N2—C6—C7	121.7 (2)	C37B—C31B—C36B	119 (2)
N2—C6—C1	115.8 (2)	C33B—C32B—C31B	121 (3)
C7—C6—C1	122.4 (2)	C33B—C32B—H32B	119.6
C8—C7—C6	118.9 (3)	C31B—C32B—H32B	119.6
C8—C7—H7	120.6	C32B—C33B—C34	122 (5)
C6—C7—H7	120.6	C32B—C33B—H33B	119.0
C9—C8—C7	119.4 (3)	C34—C33B—H33B	119.0
C9—C8—H8	120.3	C36B—C35B—C34	119 (3)
C7—C8—H8	120.3	C36B—C35B—H35B	120.7
C10—C9—C8	118.5 (2)	C34—C35B—H35B	120.7
C10—C9—H9	120.8	C35B—C36B—C31B	120 (3)
C8—C9—H9	120.8	C35B—C36B—H36B	119.9
N2—C10—C9	123.1 (3)	C31B—C36B—H36B	119.9
N2—C10—H10	118.5	C31B—C37B—C39B	119.6 (16)
C9—C10—H10	118.5	C31B—C37B—C38B	125.5 (11)
N3—C11—C12	122.1 (2)	C39B—C37B—C38B	114.3 (15)
N3—C11—C16	115.6 (2)	N7B—C38B—C37B	174.0 (15)
C12—C11—C16	122.4 (2)	N8—C39B—C37B	175.2 (19)
C13—C12—C11	118.6 (3)	C41—C40—C42	116.2 (2)
C13—C12—H12	120.7	C41—C40—C34	122.5 (2)
C11—C12—H12	120.7	C42—C40—C34	121.2 (2)
C14—C13—C12	119.6 (3)	N9—C41—C40	178.1 (4)
C14—C13—H13	120.2	N10—C42—C40	179.3 (3)
C12—C13—H13	120.2	C44—C43—C46	122.2 (2)
C13—C14—C15	118.7 (3)	C44—C43—C45	117.0 (2)
C13—C14—H14	120.6	C46—C43—C45	120.8 (2)
C15—C14—H14	120.6	C45ⁱⁱ—C44—C43	121.7 (2)
N3—C15—C14	122.7 (3)	C45ⁱⁱ—C44—H44	119.2
N3—C15—H15	118.6	C43—C44—H44	119.2
C14—C15—H15	118.6	C44ⁱⁱ—C45—C43	121.3 (2)
N4—C16—C17	121.5 (2)	C44ⁱⁱ—C45—H45	119.3
N4—C16—C11	115.9 (2)	C43—C45—H45	119.3
C17—C16—C11	122.6 (2)	C47—C46—C43	121.2 (2)
C18—C17—C16	118.7 (3)	C47—C46—C48	116.7 (2)
C18—C17—H17	120.6	C43—C46—C48	122.0 (2)
C16—C17—H17	120.6	N11—C47—C46	178.8 (3)
C19—C18—C17	120.2 (3)	N12—C48—C46	178.9 (3)
C19—C18—H18	119.9	C52—C49—C50	121.7 (2)
C17—C18—H18	119.9	C52—C49—C51	121.2 (2)
C18—C19—C20	118.3 (3)	C50—C49—C51	117.1 (3)
C18—C19—H19	120.8	C51ⁱⁱⁱ—C50—C49	121.4 (2)
C20—C19—H19	120.8	C51ⁱⁱⁱ—C50—H50	119.3
N4—C20—C19	122.5 (3)	C49—C50—H50	119.3
N4—C20—H20	118.7	C50ⁱⁱⁱ—C51—C49	121.6 (2)
C19—C20—H20	118.7	C50ⁱⁱⁱ—C51—H51	119.2
N5—C21—C22	122.1 (2)	C49—C51—H51	119.2
N5—C21—C26	114.3 (2)	C53—C52—C49	122.6 (2)
C22—C21—C26	123.6 (2)	C53—C52—C54	116.3 (3)
C21—C22—C23	119.1 (2)	C49—C52—C54	121.1 (2)
C21—C22—H22	120.5	N13—C53—C52	179.8 (3)
C23—C22—H22	120.5	N14—C54—C52	179.2 (3)
C24—C23—C22	119.3 (3)

C5—N1—C1—C2	−1.3 (4)	Ni1—N6—C26—C21	−14.8 (2)
Ni1—N1—C1—C2	178.1 (2)	N5—C21—C26—N6	16.4 (3)
C5—N1—C1—C6	179.8 (2)	C22—C21—C26—N6	−162.5 (2)
Ni1—N1—C1—C6	−0.8 (3)	N5—C21—C26—C27	−163.0 (2)
N1—C1—C2—C3	0.2 (4)	C22—C21—C26—C27	18.1 (4)
C6—C1—C2—C3	179.0 (2)	N6—C26—C27—C28	2.1 (4)
C1—C2—C3—C4	0.9 (4)	C21—C26—C27—C28	−178.5 (2)
C2—C3—C4—C5	−0.7 (4)	C26—C27—C28—C29	0.7 (4)
C1—N1—C5—C4	1.5 (4)	C27—C28—C29—C30	−2.4 (4)
Ni1—N1—C5—C4	−177.81 (19)	C26—N6—C30—C29	1.3 (4)
C3—C4—C5—N1	−0.4 (4)	Ni1—N6—C30—C29	−165.05 (19)
C10—N2—C6—C7	−3.5 (4)	C28—C29—C30—N6	1.5 (4)
Ni1—N2—C6—C7	166.0 (2)	C36A—C31A—C32A—C33A	−3.8 (8)
C10—N2—C6—C1	177.2 (2)	C37A—C31A—C32A—C33A	173.1 (7)
Ni1—N2—C6—C1	−13.3 (3)	C31A—C32A—C33A—C34	2.9 (13)
N1—C1—C6—N2	9.6 (3)	C35A—C34—C33A—C32A	−0.5 (14)
C2—C1—C6—N2	−169.3 (2)	C40—C34—C33A—C32A	−174.6 (7)
N1—C1—C6—C7	−169.7 (2)	C33A—C34—C35A—C36A	−1.0 (13)
C2—C1—C6—C7	11.4 (4)	C40—C34—C35A—C36A	173.0 (6)
N2—C6—C7—C8	0.9 (4)	C34—C35A—C36A—C31A	0.1 (11)
C1—C6—C7—C8	−179.8 (3)	C32A—C31A—C36A—C35A	2.3 (7)
C6—C7—C8—C9	2.4 (5)	C37A—C31A—C36A—C35A	−174.7 (6)
C7—C8—C9—C10	−3.0 (5)	C36A—C31A—C37A—C39A	−21.1 (6)
C6—N2—C10—C9	2.8 (4)	C32A—C31A—C37A—C39A	162.1 (5)
Ni1—N2—C10—C9	−165.1 (2)	C36A—C31A—C37A—C38A	−140.9 (4)
C8—C9—C10—N2	0.4 (5)	C32A—C31A—C37A—C38A	42.3 (5)
C15—N3—C11—C12	−3.0 (4)	C36A—C31A—C37A—C37Aⁱ	97.6 (5)
Ni1—N3—C11—C12	168.3 (2)	C32A—C31A—C37A—C37Aⁱ	−79.2 (5)
C15—N3—C11—C16	177.6 (2)	C37B—C31B—C32B—C33B	177 (3)
Ni1—N3—C11—C16	−11.1 (3)	C36B—C31B—C32B—C33B	−2 (3)
N3—C11—C12—C13	0.1 (4)	C31B—C32B—C33B—C34	−6 (5)
C16—C11—C12—C13	179.5 (3)	C35B—C34—C33B—C32B	14 (5)
C11—C12—C13—C14	2.8 (5)	C40—C34—C33B—C32B	179 (2)
C12—C13—C14—C15	−2.8 (5)	C33B—C34—C35B—C36B	−15 (5)
C11—N3—C15—C14	3.0 (4)	C40—C34—C35B—C36B	179 (2)
Ni1—N3—C15—C14	−167.2 (2)	C34—C35B—C36B—C31B	8 (4)
C13—C14—C15—N3	−0.1 (4)	C32B—C31B—C36B—C35B	1 (2)
C20—N4—C16—C17	0.1 (4)	C37B—C31B—C36B—C35B	−178 (2)
Ni1—N4—C16—C17	−177.2 (2)	C32B—C31B—C37B—C39B	179.1 (18)
C20—N4—C16—C11	−179.1 (2)	C36B—C31B—C37B—C39B	−2 (2)
Ni1—N4—C16—C11	3.6 (3)	C32B—C31B—C37B—C38B	8.8 (19)
N3—C11—C16—N4	5.0 (3)	C36B—C31B—C37B—C38B	−172.0 (14)
C12—C11—C16—N4	−174.4 (2)	C35B—C34—C40—C41	179 (2)
N3—C11—C16—C17	−174.2 (2)	C35A—C34—C40—C41	−169.8 (6)
C12—C11—C16—C17	6.4 (4)	C33A—C34—C40—C41	3.9 (8)
N4—C16—C17—C18	−1.3 (4)	C33B—C34—C40—C41	14 (2)
C11—C16—C17—C18	177.9 (2)	C35B—C34—C40—C42	−6 (2)
C16—C17—C18—C19	1.4 (5)	C35A—C34—C40—C42	5.4 (7)
C17—C18—C19—C20	−0.4 (5)	C33A—C34—C40—C42	179.2 (7)
C16—N4—C20—C19	1.0 (4)	C33B—C34—C40—C42	−171 (2)
Ni1—N4—C20—C19	177.8 (2)	C46—C43—C44—C45ⁱⁱ	178.4 (3)
C18—C19—C20—N4	−0.8 (4)	C45—C43—C44—C45ⁱⁱ	0.0 (4)
C25—N5—C21—C22	−1.5 (3)	C44—C43—C45—C44ⁱⁱ	0.0 (4)
Ni1—N5—C21—C22	169.07 (18)	C46—C43—C45—C44ⁱⁱ	−178.4 (3)
C25—N5—C21—C26	179.6 (2)	C44—C43—C46—C47	−179.7 (2)
Ni1—N5—C21—C26	−9.9 (2)	C45—C43—C46—C47	−1.4 (4)
N5—C21—C22—C23	1.0 (4)	C44—C43—C46—C48	−2.4 (4)
C26—C21—C22—C23	179.8 (2)	C45—C43—C46—C48	175.9 (2)
C21—C22—C23—C24	0.5 (4)	C52—C49—C50—C51ⁱⁱⁱ	−179.5 (3)
C22—C23—C24—C25	−1.4 (4)	C51—C49—C50—C51ⁱⁱⁱ	−0.6 (4)
C21—N5—C25—C24	0.5 (4)	C52—C49—C51—C50ⁱⁱⁱ	179.5 (3)
Ni1—N5—C25—C24	−168.87 (19)	C50—C49—C51—C50ⁱⁱⁱ	0.6 (4)
C23—C24—C25—N5	0.9 (4)	C50—C49—C52—C53	−1.1 (4)
C30—N6—C26—C27	−3.1 (3)	C51—C49—C52—C53	−179.9 (2)
Ni1—N6—C26—C27	164.63 (18)	C50—C49—C52—C54	178.3 (3)
C30—N6—C26—C21	177.5 (2)	C51—C49—C52—C54	−0.6 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···N14ⁱⁱⁱ	0.84 (1)	2.60 (2)	3.438 (8)	174 (8)
O1A—H1B···N10^iv	0.84 (1)	2.14 (2)	2.933 (5)	159 (5)
O1B—H1C···N10^iv	0.84 (1)	2.11 (2)	2.865 (5)	150 (4)
O2A—H2A···N9^v	0.85 (1)	2.22 (1)	3.068 (4)	178 (4)
O2A—H2B···N13^vi	0.85 (1)	2.15 (1)	2.993 (4)	173 (4)
O2B—H2C···N13^vi	0.85	2.05	2.803 (16)	147
O3A—H3A···O2A	0.85 (1)	2.09 (2)	2.71 (2)	130 (3)
O3A—H3B···O1A	0.85 (1)	2.09 (2)	2.85 (2)	147 (5)
O3A—H3B···O1B	0.85 (1)	2.39 (4)	3.20 (2)	160 (6)
O3B—H3C···O1B	0.85 (1)	1.99 (2)	2.84 (2)	170 (9)
O3B—H3D···O2A	0.85 (1)	2.10 (2)	2.864 (16)	148 (5)
C4—H4···N11^vii	0.95	2.58	3.350 (3)	138
C5—H5···N3	0.95	2.67	3.213 (3)	117
C7—H7···O1B^v	0.95	2.53	3.418 (7)	156
C10—H10···N6	0.95	2.63	3.168 (3)	116
C12—H12···O2B^vii	0.95	2.44	3.30 (2)	150
C15—H15···N5	0.95	2.65	3.188 (3)	117
C15—H15···N12^viii	0.95	2.68	3.369 (4)	130
C20—H20···N2	0.95	2.69	3.227 (3)	116
C22—H22···O3B	0.95	2.48	3.366 (15)	155
C25—H25···N8^viii	0.95	2.49	3.184 (3)	130
C27—H27···O3A	0.95	2.55	3.43 (2)	155
C27—H27···O3B	0.95	2.33	3.276 (18)	172
C29—H29···N8	0.95	2.67	3.432 (3)	137
C29—H29···N11ⁱⁱⁱ	0.95	2.69	3.295 (4)	123
C30—H30···N11ⁱⁱⁱ	0.95	2.63	3.279 (4)	126

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

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Disorder of the dimeric TCNQ–TCNQ unit in the crystal structure of [Ni(bpy)3]2(TCNQ–TCNQ)(TCNQ)2·6H2O (TCNQ is 7,7,8,8-tetra­cyano­quinodi­methane)

Supporting information

Key indicators

checkCIF/PLATON results

Disorder of the dimeric TCNQ–TCNQ unit in the crystal structure of [Ni(bpy)₃]₂(TCNQ–TCNQ)(TCNQ)₂·6H₂O (TCNQ is 7,7,8,8-tetracyanoquinodimethane)