In the title compound, [Ni(C
16H
36N
4)][Cu(C
10H
4N
2O
6)]·2H
2O, 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
site symmetry, with two half-cations in the asymmetric unit.
Supporting information
CCDC reference: 255461
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
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 |
Mr = 690.92 | F(000) = 726 |
Triclinic, P1 | Dx = 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 | Rint = 0.038 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
ω–2θ scans | h = −11→11 |
Absorption correction: ψ scan (North et al., 1968) | k = −14→14 |
Tmin = 0.660, Tmax = 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(Fo2) + (0.0197P)2 + 3.4692P] where P = (Fo2 + 2Fc2)/3 |
5202 reflections | (Δ/σ)max = 0.001 |
407 parameters | Δρmax = 0.45 e Å−3 |
8 restraints | Δρmin = −0.39 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | 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···O4iv | 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. |