(meso-5,7,7,12,14,14-Hexa­methyl-1,4,8,11-tetra­aza­cyclo­tetra­decane-κ4N)­nickel(II) [N,N-o-phenyl­enebis­(oxamato)-κ4O,N,N′,O′]­cuprate(II) dihydrate

Gao, E.-Q.

doi:10.1107/S1600536804026315

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(meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ⁴N)nickel(II) [N,N-o-phenylenebis(oxamato)-κ⁴O,N,N′,O′]cuprate(II) dihydrate

E.-Q. Gao

In the title compound, [Ni(C₁₆H₃₆N₄)][Cu(C₁₀H₄N₂O₆)]·2H₂O, the two complex ions, [Ni(meso-cth)]²⁺ (meso-cth is meso-5,7,7,12,14,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane) and [Cu(opba)]²⁻ [opba is o-phenylenebis(oxamate)] are hydrogen bonded to each other, resulting in two-dimensional neutral supramolecular sheets. The sheets stack, generating one-dimensional channels filled by water molecules. The Ni atoms lie on special positions of $\overline 1$ site symmetry, with two half-cations in the asymmetric unit.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026315/ng6053sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026315/ng6053Isup2.hkl Contains datablock I

CCDC reference: 255461

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
H-atom completeness 98%
Disorder in solvent or counterion
R factor = 0.029
wR factor = 0.084
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C1     -   C2     ...       1.56 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C3     -   C4     ...       1.56 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1
PLAT731_ALERT_1_C Bond    Calc     0.84(3), Rep   0.841(10) ......       3.00 su-Rat
              O1W  -H1W     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(3), Rep   0.841(10) ......       3.00 su-Rat
              O1W  -H1W     1.555   1.555
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              H O

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C26 H44 Cu1 N6 Ni1 O8
            Atom count from the _atom_site data:  C26 H43 Cu1 N6 Ni1 O8
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    2
           From the CIF: _chemical_formula_sum  C26 H44 Cu N6 Ni O8
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         52.00     52.00    0.00
           H         88.00     86.00    2.00
           Cu         2.00      2.00    0.00
           N         12.00     12.00    0.00
           Ni         2.00      2.00    0.00
           O         16.00     16.00    0.00

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   7 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
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(meso-5,7,7,12,14,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane- κ⁴N)nickel(II) [N,N-o-phenylenebis(oxamato)-κ⁴O,N,N',O']cuprate(II) dihydrate top

Crystal data top

[Ni(C₁₆H₃₆N₄)][Cu(C₁₀H₄N₂O₆)]·2H₂O	Z = 2
M_r = 690.92	F(000) = 726
Triclinic, P1	D_x = 1.552 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.0629 (8) Å	Cell parameters from 52 reflections
b = 12.4020 (8) Å	θ = 4.8–13.1°
c = 12.8630 (8) Å	µ = 1.41 mm⁻¹
α = 92.241 (5)°	T = 293 K
β = 110.245 (5)°	Prism, red
γ = 99.343 (7)°	0.32 × 0.25 × 0.20 mm
V = 1478.26 (18) Å³

Data collection top

Siemens P4 four-circle diffractometer	3616 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
ω–2θ scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = −14→14
T_min = 0.660, T_max = 0.755	l = 0→15
6239 measured reflections	3 standard reflections every 97 reflections
5202 independent reflections	intensity decay: 1.5%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0197P)² + 3.4692P] where P = (F_o² + 2F_c²)/3
5202 reflections	(Δ/σ)_max = 0.001
407 parameters	Δρ_max = 0.45 e Å⁻³
8 restraints	Δρ_min = −0.39 e Å⁻³

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cu1	0.12119 (5)	0.23869 (4)	0.49468 (4)	0.03398 (12)
Ni1	0.5000	0.5000	0.5000	0.02631 (15)
Ni2	0.0000	0.0000	0.0000	0.02949 (16)
O1	0.1632 (3)	0.3176 (2)	0.3773 (2)	0.0475 (7)
O2	0.2807 (3)	0.2978 (2)	0.6307 (2)	0.0453 (7)
O3	0.1051 (3)	0.1147 (2)	0.7694 (2)	0.0508 (7)
O4	0.3485 (3)	0.2791 (3)	0.8125 (2)	0.0652 (9)
O5	0.0566 (3)	0.3326 (3)	0.1976 (2)	0.0624 (9)
O6	−0.1600 (3)	0.1579 (2)	0.1864 (2)	0.0535 (8)
N1	−0.0544 (3)	0.1739 (2)	0.3798 (2)	0.0311 (6)
N2	0.0427 (3)	0.1551 (2)	0.5863 (2)	0.0272 (6)
N3	0.3305 (3)	0.5367 (2)	0.3892 (2)	0.0304 (6)
H3n	0.2613	0.4754	0.3763	0.036*
N4	0.4294 (3)	0.5186 (2)	0.6224 (2)	0.0318 (7)
H4n	0.3796	0.4512	0.6249	0.038*
N5	0.1009 (3)	−0.1244 (3)	0.0215 (2)	0.0334 (7)
H5n	0.0947	−0.1497	−0.0477	0.040*
N6	0.1697 (3)	0.1050 (2)	0.0059 (2)	0.0330 (7)
H6n	0.1775	0.0921	−0.0617	0.040*
C1	−0.0669 (4)	0.1967 (3)	0.2766 (3)	0.0366 (8)
C2	0.0609 (5)	0.2893 (3)	0.2821 (4)	0.0441 (10)
C3	0.2646 (4)	0.2541 (3)	0.7167 (3)	0.0434 (10)
C4	0.1272 (4)	0.1639 (3)	0.6944 (3)	0.0334 (8)
C5	−0.0915 (4)	0.0892 (3)	0.5313 (3)	0.0291 (7)
C6	−0.1726 (4)	0.0189 (3)	0.5771 (3)	0.0373 (9)
H6	−0.1370	0.0113	0.6530	0.045*
C7	−0.3067 (4)	−0.0402 (3)	0.5105 (4)	0.0468 (10)
H7	−0.3606	−0.0873	0.5419	0.056*
C8	−0.3610 (4)	−0.0296 (3)	0.3967 (3)	0.0447 (10)
H8	−0.4516	−0.0688	0.3527	0.054*
C9	−0.2801 (4)	0.0396 (3)	0.3489 (3)	0.0384 (9)
H9	−0.3159	0.0458	0.2728	0.046*
C10	−0.1461 (3)	0.0992 (3)	0.4149 (3)	0.0267 (7)
C11	0.3544 (4)	0.5455 (3)	0.2809 (3)	0.0433 (9)
H11A	0.2628	0.5317	0.2191	0.052*
H11B	0.4055	0.6184	0.2793	0.052*
C12	0.5585 (4)	0.5386 (4)	0.7273 (3)	0.0471 (10)
H12A	0.6138	0.6120	0.7343	0.057*
H12B	0.5297	0.5310	0.7916	0.057*
C13	0.2635 (4)	0.6278 (3)	0.4173 (3)	0.0396 (9)
C14	0.2149 (4)	0.5956 (3)	0.5125 (3)	0.0416 (9)
H14A	0.1576	0.5219	0.4920	0.050*
H14B	0.1518	0.6443	0.5201	0.050*
C15	0.3319 (4)	0.5974 (3)	0.6260 (3)	0.0420 (9)
H15	0.3904	0.6716	0.6462	0.050*
C16	0.1298 (5)	0.6400 (4)	0.3199 (4)	0.0681 (14)
H16A	0.1575	0.6648	0.2593	0.102*
H16B	0.0824	0.6926	0.3427	0.102*
H16C	0.0653	0.5703	0.2963	0.102*
C17	0.3767 (6)	0.7343 (3)	0.4498 (4)	0.0629 (13)
H17A	0.4631	0.7223	0.5065	0.094*
H17B	0.3398	0.7913	0.4776	0.094*
H17C	0.3980	0.7559	0.3855	0.094*
C18	0.2647 (6)	0.5727 (4)	0.7147 (4)	0.0683 (14)
H18A	0.2049	0.5009	0.6957	0.102*
H18B	0.2072	0.6265	0.7181	0.102*
H18C	0.3398	0.5752	0.7859	0.102*
C19	0.0136 (4)	−0.2140 (3)	0.0580 (3)	0.0432 (9)
H19A	0.0405	−0.2839	0.0462	0.052*
H19B	0.0311	−0.1994	0.1367	0.052*
C20	0.1413 (4)	0.2183 (3)	0.0084 (4)	0.0484 (10)
H20A	0.2014	0.2651	−0.0231	0.058*
H20B	0.1632	0.2480	0.0846	0.058*
C21	0.2569 (4)	−0.1118 (3)	0.0931 (3)	0.0411 (9)
H21	0.2646	−0.0982	0.1708	0.049*
C22	0.3459 (4)	−0.0161 (3)	0.0676 (3)	0.0385 (9)
H22A	0.3337	−0.0272	−0.0105	0.046*
H22B	0.4463	−0.0165	0.1105	0.046*
C23	0.3165 (4)	0.0975 (3)	0.0896 (3)	0.0374 (9)
C24	0.3145 (5)	−0.2167 (4)	0.0827 (4)	0.0585 (12)
H24A	0.3034	−0.2343	0.0064	0.088*
H24B	0.2617	−0.2759	0.1066	0.088*
H24C	0.4148	−0.2057	0.1285	0.088*
C25	0.4326 (4)	0.1835 (4)	0.0755 (4)	0.0520 (11)
H25A	0.5252	0.1750	0.1261	0.078*
H25B	0.4158	0.2554	0.0911	0.078*
H25C	0.4303	0.1747	0.0004	0.078*
C26	0.3130 (5)	0.1155 (4)	0.2066 (3)	0.0526 (11)
H26A	0.2333	0.0653	0.2128	0.079*
H26B	0.3020	0.1896	0.2204	0.079*
H26C	0.4014	0.1029	0.2604	0.079*
O1w	−0.1012 (5)	0.4764 (3)	0.0514 (4)	0.0994 (13)
H1w	−0.098 (7)	0.411 (2)	0.065 (6)	0.119*
O2w	0.3571 (7)	0.4477 (6)	0.9717 (6)	0.0856 (16)	0.592 (5)
H2w	0.275 (4)	0.463 (8)	0.959 (7)	0.103*	0.592 (5)
H3w	0.359 (9)	0.405 (7)	0.920 (5)	0.103*	0.592 (5)
O2w'	0.4167 (11)	0.5625 (8)	1.0335 (9)	0.0856 (16)	0.408 (5)
H4w	0.504 (3)	0.595 (8)	1.064 (8)	0.103*	0.408 (5)
H5w	0.412 (7)	0.500 (5)	1.003 (12)	0.103*	0.408 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0355 (3)	0.0323 (2)	0.0307 (2)	−0.00294 (19)	0.01179 (19)	0.00200 (18)
Ni1	0.0244 (3)	0.0230 (3)	0.0346 (3)	0.0052 (2)	0.0139 (3)	0.0048 (3)
Ni2	0.0263 (3)	0.0428 (4)	0.0237 (3)	0.0127 (3)	0.0111 (3)	0.0069 (3)
O1	0.0531 (17)	0.0374 (15)	0.0520 (18)	−0.0075 (13)	0.0254 (15)	0.0101 (13)
O2	0.0402 (15)	0.0425 (16)	0.0386 (15)	−0.0078 (12)	0.0038 (12)	−0.0042 (12)
O3	0.0598 (18)	0.070 (2)	0.0264 (14)	0.0167 (15)	0.0166 (13)	0.0141 (14)
O4	0.0527 (19)	0.079 (2)	0.0407 (18)	0.0074 (17)	−0.0070 (15)	−0.0173 (16)
O5	0.073 (2)	0.075 (2)	0.0569 (19)	0.0163 (17)	0.0412 (17)	0.0371 (17)
O6	0.0557 (18)	0.068 (2)	0.0278 (14)	0.0021 (15)	0.0077 (13)	0.0073 (14)
N1	0.0360 (16)	0.0309 (16)	0.0253 (15)	0.0047 (13)	0.0098 (13)	0.0064 (12)
N2	0.0257 (15)	0.0335 (16)	0.0221 (14)	0.0047 (12)	0.0086 (12)	0.0042 (12)
N3	0.0223 (14)	0.0256 (15)	0.0439 (17)	0.0059 (12)	0.0117 (13)	0.0062 (13)
N4	0.0335 (16)	0.0283 (15)	0.0426 (17)	0.0070 (13)	0.0239 (14)	0.0076 (13)
N5	0.0275 (15)	0.0537 (19)	0.0247 (15)	0.0184 (14)	0.0104 (12)	0.0133 (13)
N6	0.0322 (16)	0.051 (2)	0.0226 (14)	0.0125 (14)	0.0158 (13)	0.0095 (14)
C1	0.047 (2)	0.036 (2)	0.034 (2)	0.0160 (17)	0.0202 (18)	0.0064 (16)
C2	0.058 (3)	0.035 (2)	0.055 (3)	0.0190 (19)	0.035 (2)	0.0119 (19)
C3	0.039 (2)	0.047 (2)	0.036 (2)	0.0158 (18)	0.0016 (18)	−0.0130 (19)
C4	0.037 (2)	0.039 (2)	0.0282 (19)	0.0150 (16)	0.0133 (16)	0.0028 (16)
C5	0.0278 (18)	0.0317 (18)	0.0299 (18)	0.0062 (15)	0.0126 (15)	0.0053 (15)
C6	0.047 (2)	0.040 (2)	0.033 (2)	0.0114 (18)	0.0225 (18)	0.0136 (16)
C7	0.040 (2)	0.046 (2)	0.059 (3)	0.0009 (19)	0.027 (2)	0.012 (2)
C8	0.027 (2)	0.045 (2)	0.055 (3)	−0.0007 (17)	0.0114 (18)	0.0000 (19)
C9	0.033 (2)	0.044 (2)	0.033 (2)	0.0087 (17)	0.0046 (16)	0.0094 (17)
C10	0.0194 (16)	0.0287 (18)	0.0293 (18)	0.0054 (14)	0.0049 (14)	0.0032 (14)
C11	0.043 (2)	0.048 (2)	0.038 (2)	0.0101 (19)	0.0132 (18)	0.0089 (18)
C12	0.046 (2)	0.066 (3)	0.032 (2)	0.015 (2)	0.0149 (18)	−0.0024 (19)
C13	0.040 (2)	0.034 (2)	0.051 (2)	0.0208 (17)	0.0168 (19)	0.0120 (17)
C14	0.036 (2)	0.046 (2)	0.053 (2)	0.0185 (18)	0.0235 (19)	0.0000 (19)
C15	0.051 (2)	0.035 (2)	0.053 (2)	0.0178 (18)	0.030 (2)	0.0037 (18)
C16	0.062 (3)	0.091 (4)	0.061 (3)	0.051 (3)	0.016 (2)	0.018 (3)
C17	0.094 (4)	0.029 (2)	0.082 (3)	0.013 (2)	0.050 (3)	0.009 (2)
C18	0.077 (3)	0.093 (4)	0.071 (3)	0.047 (3)	0.056 (3)	0.022 (3)
C19	0.047 (2)	0.043 (2)	0.049 (2)	0.0186 (19)	0.023 (2)	0.0143 (19)
C20	0.041 (2)	0.041 (2)	0.063 (3)	0.0087 (18)	0.019 (2)	0.005 (2)
C21	0.040 (2)	0.058 (3)	0.031 (2)	0.0195 (19)	0.0136 (17)	0.0199 (18)
C22	0.0268 (19)	0.057 (2)	0.034 (2)	0.0180 (18)	0.0092 (16)	0.0096 (18)
C23	0.0278 (19)	0.060 (3)	0.0239 (18)	0.0087 (17)	0.0076 (15)	0.0082 (17)
C24	0.046 (3)	0.069 (3)	0.071 (3)	0.032 (2)	0.021 (2)	0.029 (3)
C25	0.032 (2)	0.058 (3)	0.060 (3)	0.0036 (19)	0.010 (2)	0.017 (2)
C26	0.053 (3)	0.070 (3)	0.034 (2)	0.004 (2)	0.018 (2)	−0.003 (2)
O1w	0.112 (3)	0.085 (3)	0.109 (3)	0.032 (3)	0.039 (3)	0.032 (3)
O2w	0.095 (4)	0.081 (4)	0.080 (4)	0.006 (3)	0.037 (3)	−0.011 (3)
O2w'	0.095 (4)	0.081 (4)	0.080 (4)	0.006 (3)	0.037 (3)	−0.011 (3)

Geometric parameters (Å, º) top

Cu1—N1	1.895 (3)	C12—C11ⁱ	1.490 (5)
Cu1—N2	1.887 (3)	C12—H12A	0.9700
Cu1—O1	1.959 (3)	C12—H12B	0.9700
Cu1—O2	1.936 (2)	C13—C14	1.512 (5)
Ni1—N3ⁱ	1.941 (3)	C13—C16	1.522 (6)
Ni1—N3	1.941 (3)	C13—C17	1.535 (6)
Ni1—N4ⁱ	1.959 (3)	C14—C15	1.522 (5)
Ni1—N4	1.959 (3)	C14—H14A	0.9700
Ni2—N5	1.959 (3)	C14—H14B	0.9700
Ni2—N6	1.949 (3)	C15—C18	1.533 (5)
Ni2—N6ⁱⁱ	1.949 (3)	C15—H15	0.9800
Ni2—N5ⁱⁱ	1.959 (3)	C16—H16A	0.9600
O1—C2	1.289 (5)	C16—H16B	0.9600
O2—C3	1.299 (5)	C16—H16C	0.9600
O3—C4	1.226 (4)	C17—H17A	0.9600
O4—C3	1.222 (4)	C17—H17B	0.9600
O5—C2	1.221 (5)	C17—H17C	0.9600
O6—C1	1.230 (4)	C18—H18A	0.9600
N1—C1	1.335 (4)	C18—H18B	0.9600
N1—C10	1.399 (4)	C18—H18C	0.9600
N2—C4	1.345 (4)	C19—C20ⁱⁱ	1.487 (5)
N2—C5	1.388 (4)	C19—H19A	0.9700
N3—C11	1.499 (5)	C19—H19B	0.9700
N3—C13	1.499 (4)	C20—C19ⁱⁱ	1.487 (5)
N3—H3n	0.9100	C20—H20A	0.9700
N4—C12	1.491 (5)	C20—H20B	0.9700
N4—C15	1.503 (4)	C21—C22	1.486 (5)
N4—H4n	0.9100	C21—C24	1.527 (6)
N5—C19	1.496 (5)	C21—H21	0.9800
N5—C21	1.498 (4)	C22—C23	1.521 (5)
N5—H5n	0.9100	C22—H22A	0.9700
N6—C20	1.480 (5)	C22—H22B	0.9700
N6—C23	1.518 (4)	C23—C25	1.514 (5)
N6—H6n	0.9100	C23—C26	1.527 (5)
C1—C2	1.559 (5)	C24—H24A	0.9600
C3—C4	1.563 (5)	C24—H24B	0.9600
C5—C6	1.385 (5)	C24—H24C	0.9600
C5—C10	1.423 (5)	C25—H25A	0.9600
C6—C7	1.386 (5)	C25—H25B	0.9600
C6—H6	0.9300	C25—H25C	0.9600
C7—C8	1.394 (6)	C26—H26A	0.9600
C7—H7	0.9300	C26—H26B	0.9600
C8—C9	1.392 (5)	C26—H26C	0.9600
C8—H8	0.9300	O1w—H1w	0.841 (10)
C9—C10	1.386 (5)	O2w—H2w	0.840 (10)
C9—H9	0.9300	O2w—H3w	0.838 (10)
C11—C12ⁱ	1.490 (5)	O2w'—H4w	0.848 (10)
C11—H11A	0.9700	O2w'—H5w	0.847 (10)
C11—H11B	0.9700

N1—Cu1—N2	83.86 (12)	C11ⁱ—C12—H12B	110.5
N1—Cu1—O1	84.83 (12)	N4—C12—H12B	110.5
N1—Cu1—O2	169.13 (12)	H12A—C12—H12B	108.7
N2—Cu1—O1	168.43 (12)	N3—C13—C14	107.0 (3)
N2—Cu1—O2	85.96 (11)	N3—C13—C16	111.0 (3)
O1—Cu1—O2	105.14 (12)	C14—C13—C16	107.2 (3)
N3—Ni1—N3ⁱ	180.0	N3—C13—C17	108.5 (3)
N3—Ni1—N4	93.72 (12)	C14—C13—C17	111.9 (3)
N3ⁱ—Ni1—N4ⁱ	93.72 (12)	C16—C13—C17	111.2 (4)
N3—Ni1—N4ⁱ	86.28 (12)	C13—C14—C15	117.1 (3)
N3ⁱ—Ni1—N4	86.28 (12)	C13—C14—H14A	108.0
N4—Ni1—N4ⁱ	180.0	C15—C14—H14A	108.0
N5—Ni2—N5ⁱⁱ	180.0	C13—C14—H14B	108.0
N5—Ni2—N6	93.62 (12)	C15—C14—H14B	108.0
N5—Ni2—N6ⁱⁱ	86.38 (12)	H14A—C14—H14B	107.3
N6—Ni2—N6ⁱⁱ	180.0	N4—C15—C14	111.2 (3)
N6ⁱⁱ—Ni2—N5ⁱⁱ	93.62 (12)	N4—C15—C18	111.1 (3)
N5ⁱⁱ—Ni2—N6	86.38 (12)	C14—C15—C18	110.5 (3)
C2—O1—Cu1	111.5 (2)	N4—C15—H15	107.9
C3—O2—Cu1	111.6 (2)	C14—C15—H15	107.9
C1—N1—C10	129.2 (3)	C18—C15—H15	107.9
C1—N1—Cu1	116.2 (2)	C13—C16—H16A	109.5
C10—N1—Cu1	114.2 (2)	C13—C16—H16B	109.5
C4—N2—C5	129.2 (3)	H16A—C16—H16B	109.5
C4—N2—Cu1	115.6 (2)	C13—C16—H16C	109.5
C5—N2—Cu1	115.2 (2)	H16A—C16—H16C	109.5
C11—N3—C13	112.8 (3)	H16B—C16—H16C	109.5
C11—N3—Ni1	109.4 (2)	C13—C17—H17A	109.5
C13—N3—Ni1	119.9 (2)	C13—C17—H17B	109.5
C11—N3—H3n	104.4	H17A—C17—H17B	109.5
C13—N3—H3n	104.4	C13—C17—H17C	109.5
Ni1—N3—H3n	104.4	H17A—C17—H17C	109.5
C12—N4—C15	109.6 (3)	H17B—C17—H17C	109.5
C12—N4—Ni1	106.6 (2)	C15—C18—H18A	109.5
C15—N4—Ni1	123.6 (2)	C15—C18—H18B	109.5
C12—N4—H4n	105.2	H18A—C18—H18B	109.5
C15—N4—H4n	105.2	C15—C18—H18C	109.5
Ni1—N4—H4n	105.2	H18A—C18—H18C	109.5
C19—N5—C21	109.6 (3)	H18B—C18—H18C	109.5
C19—N5—Ni2	107.4 (2)	C20ⁱⁱ—C19—N5	108.2 (3)
C21—N5—Ni2	122.0 (2)	C20ⁱⁱ—C19—H19A	110.1
C19—N5—H5n	105.6	N5—C19—H19A	110.1
C21—N5—H5n	105.6	C20ⁱⁱ—C19—H19B	110.1
Ni2—N5—H5n	105.6	N5—C19—H19B	110.1
C20—N6—C23	111.6 (3)	H19A—C19—H19B	108.4
C20—N6—Ni2	110.3 (2)	N6—C20—C19ⁱⁱ	107.9 (3)
C23—N6—Ni2	119.7 (2)	N6—C20—H20A	110.1
C20—N6—H6n	104.6	C19ⁱⁱ—C20—H20A	110.1
C23—N6—H6n	104.6	N6—C20—H20B	110.1
Ni2—N6—H6n	104.6	C19ⁱⁱ—C20—H20B	110.1
O6—C1—N1	130.3 (4)	H20A—C20—H20B	108.4
O6—C1—C2	120.4 (3)	C22—C21—N5	111.5 (3)
N1—C1—C2	109.3 (3)	C22—C21—C24	110.8 (3)
O5—C2—O1	124.0 (4)	N5—C21—C24	111.4 (3)
O5—C2—C1	118.7 (4)	C22—C21—H21	107.6
O1—C2—C1	117.3 (3)	N5—C21—H21	107.6
O4—C3—O2	124.6 (4)	C24—C21—H21	107.6
O4—C3—C4	118.6 (4)	C21—C22—C23	117.7 (3)
O2—C3—C4	116.9 (3)	C21—C22—H22A	107.9
O3—C4—N2	128.5 (3)	C23—C22—H22A	107.9
O3—C4—C3	121.8 (3)	C21—C22—H22B	107.9
N2—C4—C3	109.6 (3)	C23—C22—H22B	107.9
C6—C5—N2	127.5 (3)	H22A—C22—H22B	107.2
C6—C5—C10	119.4 (3)	C25—C23—N6	110.5 (3)
N2—C5—C10	113.1 (3)	C25—C23—C22	109.2 (3)
C5—C6—C7	120.3 (3)	N6—C23—C22	107.6 (3)
C5—C6—H6	119.9	C25—C23—C26	109.8 (3)
C7—C6—H6	119.9	N6—C23—C26	108.5 (3)
C6—C7—C8	120.4 (4)	C22—C23—C26	111.3 (3)
C6—C7—H7	119.8	C21—C24—H24A	109.5
C8—C7—H7	119.8	C21—C24—H24B	109.5
C9—C8—C7	120.2 (4)	H24A—C24—H24B	109.5
C9—C8—H8	119.9	C21—C24—H24C	109.5
C7—C8—H8	119.9	H24A—C24—H24C	109.5
C10—C9—C8	119.9 (3)	H24B—C24—H24C	109.5
C10—C9—H9	120.1	C23—C25—H25A	109.5
C8—C9—H9	120.1	C23—C25—H25B	109.5
C9—C10—N1	126.5 (3)	H25A—C25—H25B	109.5
C9—C10—C5	119.9 (3)	C23—C25—H25C	109.5
N1—C10—C5	113.6 (3)	H25A—C25—H25C	109.5
C12ⁱ—C11—N3	106.8 (3)	H25B—C25—H25C	109.5
C12ⁱ—C11—H11A	110.4	C23—C26—H26A	109.5
N3—C11—H11A	110.4	C23—C26—H26B	109.5
C12ⁱ—C11—H11B	110.4	H26A—C26—H26B	109.5
N3—C11—H11B	110.4	C23—C26—H26C	109.5
H11A—C11—H11B	108.6	H26A—C26—H26C	109.5
C11ⁱ—C12—N4	106.1 (3)	H26B—C26—H26C	109.5
C11ⁱ—C12—H12A	110.5	H2w—O2w—H3w	112.4 (19)
N4—C12—H12A	110.5	H4w—O2w'—H5w	110.5 (19)

N2—Cu1—O1—C2	−13.7 (8)	C4—N2—C5—C10	−177.8 (3)
N1—Cu1—O1—C2	−1.4 (3)	Cu1—N2—C5—C10	−1.2 (4)
O2—Cu1—O1—C2	−177.0 (3)	N2—C5—C6—C7	178.9 (3)
N2—Cu1—O2—C3	1.7 (3)	C10—C5—C6—C7	−0.9 (5)
N1—Cu1—O2—C3	22.3 (8)	C5—C6—C7—C8	0.1 (6)
O1—Cu1—O2—C3	178.4 (2)	C6—C7—C8—C9	0.8 (6)
N2—Cu1—N1—C1	−175.6 (3)	C7—C8—C9—C10	−0.9 (6)
O2—Cu1—N1—C1	163.8 (6)	C8—C9—C10—N1	−178.1 (3)
O1—Cu1—N1—C1	6.9 (3)	C8—C9—C10—C5	0.2 (5)
N2—Cu1—N1—C10	−2.1 (2)	C1—N1—C10—C9	−7.1 (6)
O2—Cu1—N1—C10	−22.8 (8)	Cu1—N1—C10—C9	−179.5 (3)
O1—Cu1—N1—C10	−179.7 (2)	C1—N1—C10—C5	174.5 (3)
N1—Cu1—N2—C4	178.9 (3)	Cu1—N1—C10—C5	2.0 (4)
O2—Cu1—N2—C4	−4.9 (2)	C6—C5—C10—C9	0.7 (5)
O1—Cu1—N2—C4	−168.7 (5)	N2—C5—C10—C9	−179.1 (3)
N1—Cu1—N2—C5	1.8 (2)	C6—C5—C10—N1	179.3 (3)
O2—Cu1—N2—C5	178.0 (2)	N2—C5—C10—N1	−0.6 (4)
O1—Cu1—N2—C5	14.2 (7)	C13—N3—C11—C12ⁱ	171.2 (3)
N4ⁱ—Ni1—N3—C11	−7.4 (2)	Ni1—N3—C11—C12ⁱ	35.1 (3)
N4—Ni1—N3—C11	172.6 (2)	C15—N4—C12—C11ⁱ	177.6 (3)
N4ⁱ—Ni1—N3—C13	−139.9 (3)	Ni1—N4—C12—C11ⁱ	−46.4 (3)
N4—Ni1—N3—C13	40.1 (3)	C11—N3—C13—C14	167.4 (3)
N3ⁱ—Ni1—N4—C12	21.7 (2)	Ni1—N3—C13—C14	−61.6 (3)
N3—Ni1—N4—C12	−158.3 (2)	C11—N3—C13—C16	50.7 (4)
N3ⁱ—Ni1—N4—C15	149.9 (3)	Ni1—N3—C13—C16	−178.3 (3)
N3—Ni1—N4—C15	−30.1 (3)	C11—N3—C13—C17	−71.7 (4)
N6—Ni2—N5—C19	161.9 (2)	Ni1—N3—C13—C17	59.3 (4)
N6ⁱⁱ—Ni2—N5—C19	−18.1 (2)	N3—C13—C14—C15	71.1 (4)
N6—Ni2—N5—C21	34.3 (3)	C16—C13—C14—C15	−169.8 (4)
N6ⁱⁱ—Ni2—N5—C21	−145.7 (3)	C17—C13—C14—C15	−47.6 (4)
N5ⁱⁱ—Ni2—N6—C20	8.2 (2)	C12—N4—C15—C14	168.7 (3)
N5—Ni2—N6—C20	−171.8 (2)	Ni1—N4—C15—C14	41.8 (4)
N5ⁱⁱ—Ni2—N6—C23	139.8 (3)	C12—N4—C15—C18	−67.8 (4)
N5—Ni2—N6—C23	−40.2 (3)	Ni1—N4—C15—C18	165.3 (3)
C10—N1—C1—O6	−0.9 (6)	C13—C14—C15—N4	−61.1 (4)
Cu1—N1—C1—O6	171.4 (3)	C13—C14—C15—C18	175.0 (3)
C10—N1—C1—C2	178.0 (3)	C21—N5—C19—C20ⁱⁱ	175.4 (3)
Cu1—N1—C1—C2	−9.7 (4)	Ni2—N5—C19—C20ⁱⁱ	41.0 (4)
Cu1—O1—C2—O5	174.4 (3)	C23—N6—C20—C19ⁱⁱ	−168.6 (3)
Cu1—O1—C2—C1	−3.6 (4)	Ni2—N6—C20—C19ⁱⁱ	−33.0 (4)
O6—C1—C2—O5	9.7 (6)	C19—N5—C21—C22	−174.1 (3)
N1—C1—C2—O5	−169.3 (4)	Ni2—N5—C21—C22	−47.5 (4)
O6—C1—C2—O1	−172.2 (4)	C19—N5—C21—C24	61.5 (4)
N1—C1—C2—O1	8.8 (5)	Ni2—N5—C21—C24	−171.9 (2)
Cu1—O2—C3—O4	−178.2 (3)	N5—C21—C22—C23	63.6 (4)
Cu1—O2—C3—C4	1.4 (4)	C24—C21—C22—C23	−171.6 (3)
C5—N2—C4—O3	0.6 (6)	C20—N6—C23—C25	−51.7 (4)
Cu1—N2—C4—O3	−176.0 (3)	Ni2—N6—C23—C25	177.4 (3)
C5—N2—C4—C3	−177.0 (3)	C20—N6—C23—C22	−170.7 (3)
Cu1—N2—C4—C3	6.4 (4)	Ni2—N6—C23—C22	58.3 (3)
O4—C3—C4—O3	−3.3 (5)	C20—N6—C23—C26	68.8 (4)
O2—C3—C4—O3	177.1 (3)	Ni2—N6—C23—C26	−62.2 (4)
O4—C3—C4—N2	174.5 (3)	C21—C22—C23—C25	171.3 (3)
O2—C3—C4—N2	−5.1 (4)	C21—C22—C23—N6	−68.8 (4)
C4—N2—C5—C6	2.4 (6)	C21—C22—C23—C26	49.9 (4)
Cu1—N2—C5—C6	179.0 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3n···O1	0.91	2.05	2.923 (4)	161
N4—H4n···O2	0.91	2.02	2.924 (4)	176
N6—H6n···O3ⁱⁱⁱ	0.91	2.09	2.894 (4)	148
N5—H5n···O6ⁱⁱ	0.91	2.11	2.962 (4)	156
O1w—H1w···O5	0.84 (1)	2.25 (5)	2.891 (5)	134 (6)
O2w—H3w···O4	0.84 (1)	2.01 (2)	2.838 (7)	168 (10)
O2w′—H4w···O4^iv	0.85 (1)	2.14 (2)	2.884 (10)	146 (4)

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

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