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Racemic crystals of the title species, (1
S/
R,2
S′/
R)-bis[(1
S,2
S)-
trans-3,3′-(1,2-cyclohexanediyldinitrilo)bis(2-methylpropane-2-thiolato)]-1κ
4N1,
N1′,
S1,
S1′;2κ
4N2,
N2′,
S2,
S2′;3κ
2S1,
S2′;4κ
2S1′,
S2;5κ
2S1′,
S2′-trichloro-3κ
Cl,4κ
Cl,5κ
Cl-tricopper(I)dinickel(II) bis(dimethylformamide) solvate, contain
C-centered columns of chiral pentanuclear [Ni
2(C
14H
28N
2S
2)
2{Cu
ICl}
3] complexes (
R,
R and
S,
S) hydrogen bonded to dimethylformamide (C
3H
7NO) solvent molecules. Intercluster C—H
Cl hydrogen bonds link the complexes to form layers parallel to the
ab plane. In each complex, three Cu
ICl groups bridge four S(thiolate) atoms of two Ni(C
14H
28N
2S
2) units, forming an Ni
2Cu
3S
4 core with the connectivity of the C atoms in bicyclo[3.3.1]nonane. Two of the Cu
I ions exhibit short contacts with Ni, suggesting weak Ni—Cu bonding. The complex molecule exhibits twofold site symmetry (site 4
e in space group
C2/
c).
Supporting information
CCDC reference: 221643
Key indicators
- Single-crystal X-ray study
- T = 223 K
- Mean (C-C) = 0.005 Å
- R factor = 0.035
- wR factor = 0.092
- Data-to-parameter ratio = 16.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level B:
ABSTM_02 Alert B The ratio of expected to reported Tmax/Tmin(RR) is > 1.50
Tmin and Tmax reported: 0.694 0.868
Tmin and Tmax expected: 0.438 0.868
RR = 1.583
Please check that your absorption correction is appropriate.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-32 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 2000).
Rac-bis[(1
S,2S)-
trans-3,3'-(1,2-cyclohexanediyldinitrilo)bis-
(2-methylpropane-2-thiolato)]-1
κ4N1,
N1',
S1,
S1';-
2
κ4N2,
N2',
S2,
S2';3
κ2S1,
S2';4
κ2S1',
S2;-
5
κ2S1',
S2'-trichloro-3
κCl,4
κCl,5
κCl-tricopper(I)- dinickel(II) bis(dimethylformamide) solvate
top
Crystal data top
[Cu3Ni2Cl3(C14H28N2S2)2]·2C3H7NO | F(000) = 2360 |
Mr = 1137.61 | Dx = 1.511 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 957 reflections |
a = 11.874 (3) Å | θ = 3.0–24.4° |
b = 20.058 (4) Å | µ = 2.36 mm−1 |
c = 21.348 (5) Å | T = 223 K |
β = 100.48 (1)° | Plate, dark orange–brown |
V = 4999.4 (19) Å3 | 0.40 × 0.30 × 0.06 mm |
Z = 4 | |
Data collection top
Bruker CCD area-detector diffractometer | 4350 independent reflections |
Radiation source: fine-focus sealed tube | 3522 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Blessing, 1995) | h = −8→14 |
Tmin = 0.694, Tmax = 0.868 | k = −20→23 |
12812 measured reflections | l = −22→25 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0545P)2 + 0.1342P] where P = (Fo2 + 2Fc2)/3 |
4350 reflections | (Δ/σ)max = 0.001 |
263 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Cu2 | 0.0000 | 0.17093 (3) | 0.7500 | 0.03928 (16) | |
Ni | 0.17797 (3) | 0.031088 (18) | 0.679617 (16) | 0.03369 (13) | |
Cu1 | −0.04823 (4) | 0.00549 (2) | 0.66571 (2) | 0.04442 (15) | 0.92 |
S1 | 0.04643 (7) | 0.10715 (4) | 0.67399 (3) | 0.0393 (2) | |
S2 | 0.18955 (7) | 0.00427 (4) | 0.77901 (3) | 0.0394 (2) | |
Cl2 | 0.0000 | 0.27912 (6) | 0.7500 | 0.0718 (4) | |
N2 | 0.2597 (2) | −0.04935 (14) | 0.66734 (12) | 0.0413 (6) | |
C8 | 0.3167 (3) | −0.04286 (16) | 0.61172 (14) | 0.0410 (8) | |
H8 | 0.3892 | −0.0190 | 0.6252 | 0.049* | |
N1 | 0.2083 (3) | 0.05945 (15) | 0.59711 (11) | 0.0413 (6) | |
C13 | 0.1723 (3) | −0.13401 (16) | 0.76803 (16) | 0.0521 (9) | |
H13A | 0.1214 | −0.1273 | 0.7281 | 0.078* | |
H13B | 0.1292 | −0.1344 | 0.8019 | 0.078* | |
H13C | 0.2113 | −0.1758 | 0.7672 | 0.078* | |
C2 | 0.1154 (3) | 0.10007 (17) | 0.56075 (14) | 0.0480 (8) | |
H2A | 0.0516 | 0.0714 | 0.5432 | 0.058* | |
H2B | 0.1424 | 0.1215 | 0.5255 | 0.058* | |
C10 | 0.2587 (3) | −0.07843 (15) | 0.77872 (13) | 0.0401 (7) | |
C7 | 0.3427 (3) | −0.10912 (18) | 0.58218 (16) | 0.0533 (9) | |
H7A | 0.2723 | −0.1341 | 0.5694 | 0.064* | |
H7B | 0.3939 | −0.1354 | 0.6133 | 0.064* | |
C4 | 0.2969 (3) | 0.01492 (19) | 0.50589 (16) | 0.0554 (9) | |
H4A | 0.2453 | 0.0409 | 0.4747 | 0.066* | |
H4B | 0.3658 | 0.0409 | 0.5196 | 0.066* | |
C1 | 0.0748 (3) | 0.15282 (16) | 0.60251 (14) | 0.0443 (8) | |
C9 | 0.3280 (3) | −0.07502 (17) | 0.72536 (14) | 0.0475 (8) | |
H9A | 0.3940 | −0.0465 | 0.7383 | 0.057* | |
H9B | 0.3555 | −0.1192 | 0.7175 | 0.057* | |
C5 | 0.3270 (4) | −0.0497 (2) | 0.47584 (16) | 0.0647 (11) | |
H5A | 0.3692 | −0.0396 | 0.4421 | 0.078* | |
H5B | 0.2570 | −0.0724 | 0.4568 | 0.078* | |
C3 | 0.2397 (3) | −0.00015 (16) | 0.56316 (14) | 0.0433 (8) | |
H3 | 0.1695 | −0.0254 | 0.5478 | 0.052* | |
C6 | 0.3986 (4) | −0.0961 (2) | 0.52387 (16) | 0.0634 (10) | |
H6A | 0.4737 | −0.0764 | 0.5379 | 0.076* | |
H6B | 0.4091 | −0.1382 | 0.5033 | 0.076* | |
C14 | 0.3394 (3) | −0.08767 (19) | 0.84267 (14) | 0.0545 (9) | |
H14A | 0.3806 | −0.1288 | 0.8422 | 0.082* | |
H14B | 0.2956 | −0.0888 | 0.8763 | 0.082* | |
H14C | 0.3926 | −0.0512 | 0.8496 | 0.082* | |
C11 | 0.1662 (4) | 0.20574 (17) | 0.62444 (19) | 0.0627 (10) | |
H11A | 0.1825 | 0.2295 | 0.5881 | 0.094* | |
H11B | 0.2347 | 0.1846 | 0.6463 | 0.094* | |
H11C | 0.1387 | 0.2364 | 0.6527 | 0.094* | |
C12 | −0.0367 (3) | 0.1845 (2) | 0.56874 (17) | 0.0671 (11) | |
H12A | −0.0225 | 0.2094 | 0.5325 | 0.101* | |
H12B | −0.0656 | 0.2139 | 0.5976 | 0.101* | |
H12C | −0.0920 | 0.1502 | 0.5548 | 0.101* | |
C20 | 0.4637 (4) | 0.8771 (2) | 0.3350 (2) | 0.0805 (13) | |
H20 | 0.4150 | 0.9105 | 0.3156 | 0.097* | |
N20 | 0.4162 (3) | 0.82035 (17) | 0.34396 (18) | 0.0708 (9) | |
O20 | 0.5632 (3) | 0.89125 (19) | 0.3489 (2) | 0.1264 (15) | |
C22 | 0.2946 (4) | 0.8096 (3) | 0.3260 (3) | 0.119 (2) | |
H22A | 0.2561 | 0.8518 | 0.3201 | 0.178* | |
H22B | 0.2676 | 0.7852 | 0.3590 | 0.178* | |
H22C | 0.2791 | 0.7847 | 0.2870 | 0.178* | |
C21 | 0.4853 (6) | 0.7680 (3) | 0.3765 (4) | 0.158 (3) | |
H21A | 0.5176 | 0.7421 | 0.3463 | 0.237* | |
H21B | 0.4389 | 0.7398 | 0.3978 | 0.237* | |
H21C | 0.5459 | 0.7870 | 0.4073 | 0.237* | |
H1N | 0.266 (3) | 0.0838 (16) | 0.6078 (15) | 0.040 (10)* | |
H2N | 0.195 (3) | −0.0756 (18) | 0.6587 (15) | 0.049 (10)* | |
Cl1 | −0.01524 (7) | −0.07899 (4) | 0.60242 (3) | 0.0496 (2) | |
Cu1A | −0.0156 (5) | −0.0217 (3) | 0.6948 (3) | 0.0450 (13)* | 0.08 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu2 | 0.0394 (3) | 0.0301 (3) | 0.0489 (3) | 0.000 | 0.0095 (2) | 0.000 |
Ni | 0.0365 (2) | 0.0336 (2) | 0.0330 (2) | 0.00049 (17) | 0.01163 (16) | 0.00024 (15) |
Cu1 | 0.0472 (3) | 0.0459 (3) | 0.0433 (3) | −0.0092 (2) | 0.0166 (2) | −0.0038 (2) |
S1 | 0.0476 (5) | 0.0307 (4) | 0.0429 (4) | −0.0013 (4) | 0.0166 (4) | 0.0027 (3) |
S2 | 0.0472 (5) | 0.0359 (4) | 0.0384 (4) | 0.0079 (4) | 0.0163 (4) | 0.0019 (3) |
Cl2 | 0.0780 (11) | 0.0281 (6) | 0.1187 (12) | 0.000 | 0.0428 (9) | 0.000 |
N2 | 0.0435 (18) | 0.0437 (16) | 0.0399 (14) | 0.0057 (14) | 0.0157 (12) | −0.0010 (12) |
C8 | 0.0405 (19) | 0.0463 (19) | 0.0402 (16) | 0.0011 (15) | 0.0176 (14) | −0.0043 (14) |
N1 | 0.0409 (17) | 0.0488 (17) | 0.0360 (13) | −0.0046 (15) | 0.0118 (12) | 0.0013 (12) |
C13 | 0.072 (3) | 0.0378 (19) | 0.0498 (18) | 0.0081 (18) | 0.0188 (17) | 0.0024 (15) |
C2 | 0.052 (2) | 0.056 (2) | 0.0368 (16) | 0.0034 (17) | 0.0099 (15) | 0.0118 (15) |
C10 | 0.044 (2) | 0.0379 (18) | 0.0397 (15) | 0.0135 (15) | 0.0109 (14) | 0.0037 (13) |
C7 | 0.060 (2) | 0.056 (2) | 0.0497 (18) | 0.0039 (18) | 0.0247 (17) | −0.0101 (16) |
C4 | 0.056 (2) | 0.072 (2) | 0.0441 (18) | 0.0033 (19) | 0.0252 (17) | 0.0043 (17) |
C1 | 0.049 (2) | 0.0427 (19) | 0.0429 (16) | 0.0023 (16) | 0.0140 (15) | 0.0113 (14) |
C9 | 0.047 (2) | 0.055 (2) | 0.0425 (16) | 0.0175 (17) | 0.0144 (15) | 0.0035 (15) |
C5 | 0.069 (3) | 0.089 (3) | 0.0435 (18) | −0.004 (2) | 0.0288 (18) | −0.0124 (19) |
C3 | 0.043 (2) | 0.055 (2) | 0.0362 (15) | −0.0019 (16) | 0.0173 (14) | −0.0029 (14) |
C6 | 0.077 (3) | 0.069 (3) | 0.053 (2) | 0.007 (2) | 0.0322 (19) | −0.0112 (18) |
C14 | 0.057 (2) | 0.063 (2) | 0.0418 (17) | 0.0182 (19) | 0.0059 (16) | 0.0012 (16) |
C11 | 0.073 (3) | 0.042 (2) | 0.079 (2) | −0.0055 (19) | 0.030 (2) | 0.0100 (19) |
C12 | 0.071 (3) | 0.072 (3) | 0.059 (2) | 0.022 (2) | 0.0130 (19) | 0.018 (2) |
C20 | 0.061 (3) | 0.063 (3) | 0.115 (4) | −0.001 (2) | 0.008 (3) | −0.011 (3) |
N20 | 0.049 (2) | 0.054 (2) | 0.107 (3) | 0.0014 (17) | 0.0049 (18) | −0.0177 (19) |
O20 | 0.055 (2) | 0.099 (3) | 0.216 (5) | −0.024 (2) | 0.000 (2) | −0.023 (3) |
C22 | 0.063 (3) | 0.094 (4) | 0.196 (6) | −0.020 (3) | 0.019 (4) | −0.030 (4) |
C21 | 0.143 (7) | 0.099 (5) | 0.216 (8) | 0.018 (4) | −0.008 (5) | 0.042 (5) |
Cl1 | 0.0514 (5) | 0.0604 (5) | 0.0391 (4) | −0.0092 (4) | 0.0141 (4) | −0.0126 (4) |
Geometric parameters (Å, º) top
Ni—S1 | 2.1710 (9) | C7—H7A | 0.97 |
Ni—S2 | 2.1690 (9) | C7—H7B | 0.97 |
Ni—N1 | 1.946 (2) | C4—C5 | 1.518 (5) |
Ni—N2 | 1.925 (3) | C4—C3 | 1.533 (4) |
Cu1—Cl1 | 2.2455 (10) | C4—H4A | 0.97 |
Cu1A—Cl1 | 2.282 (5) | C4—H4B | 0.97 |
Cu1—S1 | 2.3196 (10) | C1—C12 | 1.526 (5) |
Cu1A—S1 | 2.746 (6) | C1—C11 | 1.529 (5) |
Cu1—S2i | 2.2202 (9) | C9—H9A | 0.97 |
S2—Cu1Ai | 2.296 (6) | C9—H9B | 0.97 |
Ni—Cu1 | 2.6973 (8) | C5—C6 | 1.523 (5) |
Ni—Cu1A | 2.604 (5) | C5—H5A | 0.97 |
Cu2—Cl2 | 2.1699 (14) | C5—H5B | 0.97 |
Cu2—S1 | 2.2134 (8) | C3—H3 | 0.98 |
Cu1—Cu1A | 0.863 (7) | C6—H6A | 0.97 |
Cu1—Cu1Ai | 2.987 (6) | C6—H6B | 0.97 |
S1—C1 | 1.862 (3) | C14—H14A | 0.96 |
S2—C10 | 1.851 (3) | C14—H14B | 0.96 |
S2—Cu1A | 2.801 (6) | C14—H14C | 0.96 |
N2—C9 | 1.446 (4) | C11—H11A | 0.96 |
N2—C8 | 1.476 (4) | C11—H11B | 0.96 |
N2—H2N | 0.92 (3) | C11—H11C | 0.96 |
C8—C3 | 1.517 (5) | C12—H12A | 0.96 |
C8—C7 | 1.526 (4) | C12—H12B | 0.96 |
C8—H8 | 0.98 | C12—H12C | 0.96 |
N1—C2 | 1.474 (4) | C20—O20 | 1.199 (5) |
N1—C3 | 1.480 (4) | C20—N20 | 1.300 (5) |
N1—H1N | 0.84 (3) | C20—H20 | 0.93 |
C13—C10 | 1.504 (5) | N20—C21 | 1.432 (7) |
C13—H13A | 0.96 | N20—C22 | 1.441 (5) |
C13—H13B | 0.96 | C22—H22A | 0.96 |
C13—H13C | 0.96 | C22—H22B | 0.96 |
C2—C1 | 1.518 (4) | C22—H22C | 0.96 |
C2—H2A | 0.97 | C21—H21A | 0.96 |
C2—H2B | 0.97 | C21—H21B | 0.96 |
C10—C9 | 1.523 (4) | C21—H21C | 0.96 |
C10—C14 | 1.530 (4) | Cu1A—Cu1Ai | 2.320 (12) |
C7—C6 | 1.536 (4) | | |
| | | |
N2—Ni—N1 | 86.61 (11) | C3—C4—H4B | 109.7 |
N2—Ni—S2 | 88.94 (8) | H4A—C4—H4B | 108.2 |
N1—Ni—S2 | 165.65 (9) | C2—C1—C12 | 110.7 (3) |
N2—Ni—S1 | 163.11 (9) | C2—C1—C11 | 112.3 (3) |
N1—Ni—S1 | 89.66 (9) | C12—C1—C11 | 111.2 (3) |
S2—Ni—S1 | 98.36 (3) | C2—C1—S1 | 105.2 (2) |
N2—Ni—Cu1 | 110.01 (9) | C12—C1—S1 | 108.8 (2) |
N1—Ni—Cu1 | 107.49 (9) | C11—C1—S1 | 108.3 (2) |
S2—Ni—Cu1 | 86.86 (3) | N2—C9—C10 | 111.2 (3) |
S1—Ni—Cu1 | 55.65 (3) | N2—C9—H9A | 109.4 |
S2i—Cu1—Cl1 | 122.88 (3) | C10—C9—H9A | 109.4 |
S2i—Cu1—S1 | 111.83 (3) | N2—C9—H9B | 109.4 |
Cl1—Cu1—S1 | 125.03 (3) | C10—C9—H9B | 109.4 |
S2i—Cu1—Ni | 141.01 (3) | H9A—C9—H9B | 108.0 |
Cl1—Cu1—Ni | 86.03 (3) | C4—C5—C6 | 112.5 (3) |
S1—Cu1—Ni | 50.60 (2) | C4—C5—H5A | 109.1 |
Cl2—Cu2—S1 | 125.31 (2) | C6—C5—H5A | 109.1 |
S1i—Cu2—S1 | 109.39 (5) | C4—C5—H5B | 109.1 |
N2—Ni—Cu1A | 98.88 (16) | C6—C5—H5B | 109.1 |
N1—Ni—Cu1A | 122.97 (16) | H5A—C5—H5B | 107.8 |
S2—Ni—Cu1A | 71.21 (14) | N1—C3—C8 | 107.2 (2) |
S1—Ni—Cu1A | 69.54 (14) | N1—C3—C4 | 114.8 (3) |
Cu1A—Ni—Cu1 | 18.64 (14) | C8—C3—C4 | 110.9 (3) |
Cu1A—Cu1—S2i | 84.0 (4) | N1—C3—H3 | 107.9 |
Cu1A—Cu1—Cl1 | 81.4 (3) | C8—C3—H3 | 107.9 |
Cu1A—Cu1—S1 | 110.7 (4) | C4—C3—H3 | 107.9 |
Cu1A—Cu1—Ni | 74.6 (4) | C5—C6—C7 | 112.2 (3) |
Cu1A—Cu1—Cu1Ai | 33.8 (3) | C5—C6—H6A | 109.2 |
S2i—Cu1—Cu1Ai | 63.08 (11) | C7—C6—H6A | 109.2 |
Cl1—Cu1—Cu1Ai | 114.94 (11) | C5—C6—H6B | 109.2 |
S1—Cu1—Cu1Ai | 93.05 (13) | C7—C6—H6B | 109.2 |
Ni—Cu1—Cu1Ai | 81.84 (11) | H6A—C6—H6B | 107.9 |
C1—S1—Ni | 98.96 (11) | C10—C14—H14A | 109.5 |
C1—S1—Cu2 | 115.00 (11) | C10—C14—H14B | 109.5 |
Ni—S1—Cu2 | 129.66 (4) | H14A—C14—H14B | 109.5 |
C1—S1—Cu1 | 121.82 (11) | C10—C14—H14C | 109.5 |
Ni—S1—Cu1 | 73.75 (3) | H14A—C14—H14C | 109.5 |
Cu2—S1—Cu1 | 112.46 (3) | H14B—C14—H14C | 109.5 |
C1—S1—Cu1A | 133.57 (16) | C1—C11—H11A | 109.5 |
Ni—S1—Cu1A | 62.67 (12) | C1—C11—H11B | 109.5 |
Cu2—S1—Cu1A | 108.40 (11) | H11A—C11—H11B | 109.5 |
C10—S2—Ni | 99.69 (9) | C1—C11—H11C | 109.5 |
C10—S2—Cu1i | 112.96 (10) | H11A—C11—H11C | 109.5 |
Ni—S2—Cu1i | 126.70 (4) | H11B—C11—H11C | 109.5 |
C10—S2—Cu1Ai | 102.49 (18) | C1—C12—H12A | 109.5 |
Ni—S2—Cu1Ai | 113.27 (15) | C1—C12—H12B | 109.5 |
C10—S2—Cu1A | 99.52 (16) | H12A—C12—H12B | 109.5 |
Ni—S2—Cu1A | 61.65 (12) | C1—C12—H12C | 109.5 |
Cu1i—S2—Cu1A | 71.96 (11) | H12A—C12—H12C | 109.5 |
Cu1Ai—S2—Cu1A | 53.0 (2) | H12B—C12—H12C | 109.5 |
C9—N2—C8 | 117.0 (3) | O20—C20—N20 | 127.2 (5) |
C9—N2—Ni | 113.6 (2) | O20—C20—H20 | 116.4 |
C8—N2—Ni | 110.61 (19) | N20—C20—H20 | 116.4 |
C9—N2—H2N | 107 (2) | C20—N20—C21 | 119.2 (5) |
C8—N2—H2N | 112 (2) | C20—N20—C22 | 122.1 (4) |
Ni—N2—H2N | 95 (2) | C21—N20—C22 | 118.5 (5) |
N2—C8—C3 | 107.0 (2) | N20—C22—H22A | 109.5 |
N2—C8—C7 | 114.3 (3) | N20—C22—H22B | 109.5 |
C3—C8—C7 | 110.6 (3) | H22A—C22—H22B | 109.5 |
N2—C8—H8 | 108.3 | N20—C22—H22C | 109.5 |
C3—C8—H8 | 108.3 | H22A—C22—H22C | 109.5 |
C7—C8—H8 | 108.3 | H22B—C22—H22C | 109.5 |
C2—N1—C3 | 114.8 (3) | N20—C21—H21A | 109.5 |
C2—N1—Ni | 113.2 (2) | N20—C21—H21B | 109.5 |
C3—N1—Ni | 108.15 (19) | H21A—C21—H21B | 109.5 |
C2—N1—H1N | 109 (2) | N20—C21—H21C | 109.5 |
C3—N1—H1N | 110 (2) | H21A—C21—H21C | 109.5 |
Ni—N1—H1N | 102 (2) | H21B—C21—H21C | 109.5 |
C10—C13—H13A | 109.5 | Cu1—Cu1A—Cl1 | 76.6 (4) |
C10—C13—H13B | 109.5 | Cu1—Cu1A—S2i | 74.1 (4) |
H13A—C13—H13B | 109.5 | Cl1—Cu1A—S2i | 117.9 (3) |
C10—C13—H13C | 109.5 | Cu1—Cu1A—Cu1Ai | 134.3 (4) |
H13A—C13—H13C | 109.5 | Cl1—Cu1A—Cu1Ai | 148.6 (2) |
H13B—C13—H13C | 109.5 | S2i—Cu1A—Cu1Ai | 74.7 (3) |
N1—C2—C1 | 111.3 (3) | Cu1—Cu1A—Ni | 86.8 (4) |
N1—C2—H2A | 109.4 | Cl1—Cu1A—Ni | 87.54 (17) |
C1—C2—H2A | 109.4 | S2i—Cu1A—Ni | 142.3 (3) |
N1—C2—H2B | 109.4 | Cu1Ai—Cu1A—Ni | 98.3 (3) |
C1—C2—H2B | 109.4 | Cu1—Cu1A—S1 | 52.2 (3) |
H2A—C2—H2B | 108.0 | Cl1—Cu1A—S1 | 106.9 (2) |
C13—C10—C9 | 111.5 (3) | S2i—Cu1A—S1 | 96.0 (2) |
C13—C10—C14 | 110.2 (3) | Cu1Ai—Cu1A—S1 | 99.57 (16) |
C9—C10—C14 | 109.7 (3) | Ni—Cu1A—S1 | 47.79 (10) |
C13—C10—S2 | 112.0 (2) | Cu1—Cu1A—S2 | 124.6 (4) |
C9—C10—S2 | 105.2 (2) | Cl1—Cu1A—S2 | 120.7 (2) |
C14—C10—S2 | 108.2 (2) | S2i—Cu1A—S2 | 121.1 (2) |
C8—C7—C6 | 109.6 (3) | Cu1Ai—Cu1A—S2 | 52.3 (2) |
C8—C7—H7A | 109.7 | Ni—Cu1A—S2 | 47.14 (10) |
C6—C7—H7A | 109.7 | S1—Cu1A—S2 | 72.60 (13) |
C8—C7—H7B | 109.7 | Cu1—Cu1A—Cu1i | 126.9 (4) |
C6—C7—H7B | 109.7 | Cl1—Cu1A—Cu1i | 156.0 (3) |
H7A—C7—H7B | 108.2 | S2i—Cu1A—Cu1i | 77.98 (15) |
C5—C4—C3 | 109.9 (3) | Cu1Ai—Cu1A—Cu1i | 11.94 (14) |
C5—C4—H4A | 109.7 | Ni—Cu1A—Cu1i | 88.85 (17) |
C3—C4—H4A | 109.7 | S1—Cu1A—Cu1i | 87.83 (15) |
C5—C4—H4B | 109.7 | S2—Cu1A—Cu1i | 44.97 (9) |
| | | |
N2—Ni—Cu1—Cu1A | 55.6 (4) | Ni—N2—C9—C10 | 48.8 (3) |
N1—Ni—Cu1—Cu1A | 148.3 (4) | C13—C10—C9—N2 | 72.7 (4) |
S2—Ni—Cu1—Cu1A | −32.2 (4) | C14—C10—C9—N2 | −165.1 (3) |
S1—Ni—Cu1—Cu1A | −134.5 (4) | S2—C10—C9—N2 | −48.9 (3) |
N2—Ni—Cu1—S2i | 114.56 (9) | C3—C4—C5—C6 | −53.8 (4) |
N1—Ni—Cu1—S2i | −152.65 (10) | C2—N1—C3—C8 | −168.2 (3) |
S2—Ni—Cu1—S2i | 26.84 (4) | Ni—N1—C3—C8 | −40.7 (3) |
S1—Ni—Cu1—S2i | −75.52 (5) | C2—N1—C3—C4 | 68.1 (4) |
Cu1A—Ni—Cu1—S2i | 59.0 (4) | Ni—N1—C3—C4 | −164.4 (3) |
N2—Ni—Cu1—Cl1 | −26.62 (8) | N2—C8—C3—N1 | 48.8 (3) |
N1—Ni—Cu1—Cl1 | 66.17 (10) | C7—C8—C3—N1 | 173.9 (3) |
S2—Ni—Cu1—Cl1 | −114.35 (4) | N2—C8—C3—C4 | 174.7 (3) |
S1—Ni—Cu1—Cl1 | 143.30 (4) | C7—C8—C3—C4 | −60.2 (4) |
Cu1A—Ni—Cu1—Cl1 | −82.2 (4) | C5—C4—C3—N1 | 178.9 (3) |
N2—Ni—Cu1—S1 | −169.92 (8) | C5—C4—C3—C8 | 57.3 (4) |
N1—Ni—Cu1—S1 | −77.13 (9) | C4—C5—C6—C7 | 53.3 (5) |
S2—Ni—Cu1—S1 | 102.35 (3) | C8—C7—C6—C5 | −54.2 (4) |
Cu1A—Ni—Cu1—S1 | 134.5 (4) | O20—C20—N20—C21 | 3.2 (8) |
N2—Ni—Cu1—Cu1Ai | 89.29 (14) | O20—C20—N20—C22 | 178.9 (5) |
N1—Ni—Cu1—Cu1Ai | −177.92 (15) | S2i—Cu1—Cl1—Cu1A | −77.0 (4) |
S2—Ni—Cu1—Cu1Ai | 1.56 (12) | S1—Cu1—Cl1—Cu1A | 109.3 (4) |
S1—Ni—Cu1—Cu1Ai | −100.79 (12) | Ni—Cu1—Cl1—Cu1A | 75.0 (4) |
Cu1A—Ni—Cu1—Cu1Ai | 33.7 (3) | Cu1Ai—Cu1—Cl1—Cu1A | −4.1 (5) |
N2—Ni—S1—C1 | −86.2 (3) | S2i—Cu1—Cu1A—Cl1 | 124.62 (9) |
N1—Ni—S1—C1 | −9.08 (14) | S1—Cu1—Cu1A—Cl1 | −124.30 (12) |
S2—Ni—S1—C1 | 158.98 (11) | Ni—Cu1—Cu1A—Cl1 | −88.22 (11) |
Cu1A—Ni—S1—C1 | −134.74 (18) | Cu1Ai—Cu1—Cu1A—Cl1 | 173.3 (7) |
Cu1—Ni—S1—C1 | −120.67 (11) | Cl1—Cu1—Cu1A—S2i | −124.62 (9) |
N2—Ni—S1—Cu2 | 140.5 (3) | S1—Cu1—Cu1A—S2i | 111.08 (13) |
N1—Ni—S1—Cu2 | −142.43 (10) | Ni—Cu1—Cu1A—S2i | 147.16 (13) |
S2—Ni—S1—Cu2 | 25.63 (6) | Cu1Ai—Cu1—Cu1A—S2i | 48.6 (7) |
Cu1A—Ni—S1—Cu2 | 91.90 (14) | S2i—Cu1—Cu1A—Cu1Ai | −48.6 (7) |
Cu1—Ni—S1—Cu2 | 105.98 (5) | Cl1—Cu1—Cu1A—Cu1Ai | −173.3 (7) |
N2—Ni—S1—Cu1 | 34.5 (3) | S1—Cu1—Cu1A—Cu1Ai | 62.4 (8) |
N1—Ni—S1—Cu1 | 111.59 (9) | Ni—Cu1—Cu1A—Cu1Ai | 98.5 (7) |
S2—Ni—S1—Cu1 | −80.35 (3) | S2i—Cu1—Cu1A—Ni | −147.16 (13) |
Cu1A—Ni—S1—Cu1 | −14.08 (13) | Cl1—Cu1—Cu1A—Ni | 88.22 (11) |
N2—Ni—S1—Cu1A | 48.6 (3) | S1—Cu1—Cu1A—Ni | −36.1 (2) |
N1—Ni—S1—Cu1A | 125.67 (16) | Cu1Ai—Cu1—Cu1A—Ni | −98.5 (7) |
S2—Ni—S1—Cu1A | −66.28 (14) | S2i—Cu1—Cu1A—S1 | −111.08 (13) |
Cu1—Ni—S1—Cu1A | 14.08 (13) | Cl1—Cu1—Cu1A—S1 | 124.30 (12) |
Cl2—Cu2—S1—C1 | −5.47 (13) | Ni—Cu1—Cu1A—S1 | 36.1 (2) |
S1i—Cu2—S1—C1 | 174.53 (13) | Cu1Ai—Cu1—Cu1A—S1 | −62.4 (8) |
Cl2—Cu2—S1—Ni | 122.11 (4) | S2i—Cu1—Cu1A—S2 | −117.2 (4) |
S1i—Cu2—S1—Ni | −57.89 (4) | Cl1—Cu1—Cu1A—S2 | 118.2 (4) |
Cl2—Cu2—S1—Cu1 | −150.79 (2) | S1—Cu1—Cu1A—S2 | −6.1 (5) |
S1i—Cu2—S1—Cu1 | 29.21 (2) | Ni—Cu1—Cu1A—S2 | 30.0 (3) |
Cl2—Cu2—S1—Cu1A | −168.54 (14) | Cu1Ai—Cu1—Cu1A—S2 | −68.5 (6) |
S1i—Cu2—S1—Cu1A | 11.46 (14) | S2i—Cu1—Cu1A—Cu1i | −61.0 (4) |
Cu1A—Cu1—S1—C1 | 137.8 (4) | Cl1—Cu1—Cu1A—Cu1i | 174.4 (5) |
S2i—Cu1—S1—C1 | −130.43 (13) | S1—Cu1—Cu1A—Cu1i | 50.1 (5) |
Cl1—Cu1—S1—C1 | 43.84 (14) | Ni—Cu1—Cu1A—Cu1i | 86.2 (4) |
Ni—Cu1—S1—C1 | 90.58 (13) | Cu1Ai—Cu1—Cu1A—Cu1i | −12.4 (3) |
Cu1Ai—Cu1—S1—C1 | 167.42 (16) | Cu1—Cl1—Cu1A—S2i | 63.6 (4) |
Cu1A—Cu1—S1—Ni | 47.3 (4) | Cu1—Cl1—Cu1A—Cu1Ai | 170.7 (11) |
S2i—Cu1—S1—Ni | 138.99 (4) | Cu1—Cl1—Cu1A—Ni | −87.3 (4) |
Cl1—Cu1—S1—Ni | −46.73 (5) | Cu1—Cl1—Cu1A—S1 | −43.0 (3) |
Cu1Ai—Cu1—S1—Ni | 76.84 (10) | Cu1—Cl1—Cu1A—S2 | −122.5 (5) |
Cu1A—Cu1—S1—Cu2 | −79.5 (4) | Cu1—Cl1—Cu1A—Cu1i | −168.9 (9) |
S2i—Cu1—S1—Cu2 | 12.21 (5) | N2—Ni—Cu1A—Cu1 | −128.3 (3) |
Cl1—Cu1—S1—Cu2 | −173.52 (4) | N1—Ni—Cu1A—Cu1 | −36.6 (4) |
Ni—Cu1—S1—Cu2 | −126.78 (4) | S2—Ni—Cu1A—Cu1 | 145.8 (4) |
Cu1Ai—Cu1—S1—Cu2 | −49.95 (11) | S1—Ni—Cu1A—Cu1 | 38.9 (3) |
S2i—Cu1—S1—Cu1A | 91.7 (4) | N2—Ni—Cu1A—Cl1 | −51.6 (2) |
Cl1—Cu1—S1—Cu1A | −94.0 (4) | N1—Ni—Cu1A—Cl1 | 40.1 (3) |
Ni—Cu1—S1—Cu1A | −47.3 (4) | S2—Ni—Cu1A—Cl1 | −137.4 (2) |
Cu1Ai—Cu1—S1—Cu1A | 29.6 (4) | S1—Ni—Cu1A—Cl1 | 115.6 (2) |
N2—Ni—S2—C10 | −4.10 (14) | Cu1—Ni—Cu1A—Cl1 | 76.7 (3) |
N1—Ni—S2—C10 | −76.0 (4) | N2—Ni—Cu1A—S2i | 173.1 (4) |
S1—Ni—S2—C10 | 160.62 (11) | N1—Ni—Cu1A—S2i | −95.2 (4) |
Cu1A—Ni—S2—C10 | 95.65 (17) | S2—Ni—Cu1A—S2i | 87.3 (4) |
Cu1—Ni—S2—C10 | 106.01 (11) | S1—Ni—Cu1A—S2i | −19.6 (4) |
N2—Ni—S2—Cu1i | −132.47 (10) | Cu1—Ni—Cu1A—S2i | −58.6 (4) |
N1—Ni—S2—Cu1i | 155.6 (4) | N2—Ni—Cu1A—Cu1Ai | 97.33 (14) |
S1—Ni—S2—Cu1i | 32.24 (5) | N1—Ni—Cu1A—Cu1Ai | −170.95 (15) |
Cu1A—Ni—S2—Cu1i | −32.72 (14) | S2—Ni—Cu1A—Cu1Ai | 11.51 (11) |
Cu1—Ni—S2—Cu1i | −22.36 (4) | S1—Ni—Cu1A—Cu1Ai | −95.40 (13) |
N2—Ni—S2—Cu1Ai | −112.30 (19) | Cu1—Ni—Cu1A—Cu1Ai | −134.3 (4) |
N1—Ni—S2—Cu1Ai | 175.8 (4) | N2—Ni—Cu1A—S1 | −167.27 (8) |
S1—Ni—S2—Cu1Ai | 52.42 (17) | N1—Ni—Cu1A—S1 | −75.55 (14) |
Cu1A—Ni—S2—Cu1Ai | −12.54 (10) | S2—Ni—Cu1A—S1 | 106.91 (7) |
Cu1—Ni—S2—Cu1Ai | −2.19 (17) | Cu1—Ni—Cu1A—S1 | −38.9 (3) |
N2—Ni—S2—Cu1A | −99.75 (16) | N2—Ni—Cu1A—S2 | 85.82 (9) |
N1—Ni—S2—Cu1A | −171.6 (4) | N1—Ni—Cu1A—S2 | 177.54 (11) |
S1—Ni—S2—Cu1A | 64.96 (14) | S1—Ni—Cu1A—S2 | −106.91 (7) |
Cu1—Ni—S2—Cu1A | 10.36 (14) | Cu1—Ni—Cu1A—S2 | −145.8 (4) |
N1—Ni—N2—C9 | 143.6 (2) | N2—Ni—Cu1A—Cu1i | 104.61 (13) |
S2—Ni—N2—C9 | −22.8 (2) | N1—Ni—Cu1A—Cu1i | −163.67 (11) |
S1—Ni—N2—C9 | −138.9 (2) | S2—Ni—Cu1A—Cu1i | 18.79 (8) |
Cu1A—Ni—N2—C9 | −93.6 (3) | S1—Ni—Cu1A—Cu1i | −88.12 (12) |
Cu1—Ni—N2—C9 | −109.1 (2) | Cu1—Ni—Cu1A—Cu1i | −127.0 (4) |
N1—Ni—N2—C8 | 9.7 (2) | C1—S1—Cu1A—Cu1 | −51.9 (5) |
S2—Ni—N2—C8 | −156.6 (2) | Ni—S1—Cu1A—Cu1 | −127.5 (4) |
S1—Ni—N2—C8 | 87.3 (4) | Cu2—S1—Cu1A—Cu1 | 106.7 (3) |
Cu1A—Ni—N2—C8 | 132.6 (3) | C1—S1—Cu1A—Cl1 | 5.2 (4) |
Cu1—Ni—N2—C8 | 117.1 (2) | Ni—S1—Cu1A—Cl1 | −70.30 (18) |
C9—N2—C8—C3 | −166.4 (3) | Cu2—S1—Cu1A—Cl1 | 163.88 (16) |
Ni—N2—C8—C3 | −34.3 (3) | Cu1—S1—Cu1A—Cl1 | 57.2 (3) |
C9—N2—C8—C7 | 70.8 (4) | C1—S1—Cu1A—S2i | −116.4 (2) |
Ni—N2—C8—C7 | −157.1 (2) | Ni—S1—Cu1A—S2i | 168.1 (2) |
N2—Ni—N1—C2 | 146.2 (2) | Cu2—S1—Cu1A—S2i | 42.3 (2) |
S2—Ni—N1—C2 | −141.6 (3) | Cu1—S1—Cu1A—S2i | −64.5 (3) |
S1—Ni—N1—C2 | −17.3 (2) | C1—S1—Cu1A—Cu1Ai | 168.1 (2) |
Cu1A—Ni—N1—C2 | 47.8 (3) | Ni—S1—Cu1A—Cu1Ai | 92.6 (3) |
Cu1—Ni—N1—C2 | 36.3 (2) | Cu2—S1—Cu1A—Cu1Ai | −33.2 (3) |
N2—Ni—N1—C3 | 17.8 (2) | Cu1—S1—Cu1A—Cu1Ai | −139.9 (6) |
S2—Ni—N1—C3 | 90.0 (4) | C1—S1—Cu1A—Ni | 75.5 (2) |
S1—Ni—N1—C3 | −145.7 (2) | Cu2—S1—Cu1A—Ni | −125.81 (6) |
Cu1A—Ni—N1—C3 | −80.6 (3) | Cu1—S1—Cu1A—Ni | 127.5 (4) |
Cu1—Ni—N1—C3 | −92.1 (2) | C1—S1—Cu1A—S2 | 122.85 (19) |
C3—N1—C2—C1 | 170.2 (3) | Ni—S1—Cu1A—S2 | 47.31 (7) |
Ni—N1—C2—C1 | 45.3 (3) | Cu2—S1—Cu1A—S2 | −78.51 (10) |
Ni—S2—C10—C13 | −93.3 (2) | Cu1—S1—Cu1A—S2 | 174.8 (4) |
Cu1i—S2—C10—C13 | 43.7 (2) | C1—S1—Cu1A—Cu1i | 165.96 (15) |
Cu1Ai—S2—C10—C13 | 23.4 (3) | Ni—S1—Cu1A—Cu1i | 90.41 (14) |
Cu1A—S2—C10—C13 | −30.7 (2) | Cu2—S1—Cu1A—Cu1i | −35.40 (15) |
Ni—S2—C10—C9 | 28.0 (2) | Cu1—S1—Cu1A—Cu1i | −142.1 (4) |
Cu1i—S2—C10—C9 | 164.92 (19) | C10—S2—Cu1A—Cu1 | −138.9 (5) |
Cu1Ai—S2—C10—C9 | 144.6 (3) | Ni—S2—Cu1A—Cu1 | −42.9 (5) |
Cu1A—S2—C10—C9 | 90.6 (2) | Cu1i—S2—Cu1A—Cu1 | 110.0 (5) |
Ni—S2—C10—C14 | 145.1 (2) | Cu1Ai—S2—Cu1A—Cu1 | 122.6 (5) |
Cu1i—S2—C10—C14 | −77.9 (2) | C10—S2—Cu1A—Cl1 | −44.1 (3) |
Cu1Ai—S2—C10—C14 | −98.2 (3) | Ni—S2—Cu1A—Cl1 | 51.8 (2) |
Cu1A—S2—C10—C14 | −152.3 (2) | Cu1i—S2—Cu1A—Cl1 | −155.3 (3) |
N2—C8—C7—C6 | 178.4 (3) | Cu1Ai—S2—Cu1A—Cl1 | −142.68 (19) |
C3—C8—C7—C6 | 57.7 (4) | C10—S2—Cu1A—S2i | 129.6 (3) |
N1—C2—C1—C12 | −168.1 (3) | Ni—S2—Cu1A—S2i | −134.5 (3) |
N1—C2—C1—C11 | 66.9 (4) | Cu1i—S2—Cu1A—S2i | 18.4 (2) |
N1—C2—C1—S1 | −50.7 (3) | Cu1Ai—S2—Cu1A—S2i | 31.0 (4) |
Ni—S1—C1—C2 | 32.9 (2) | C10—S2—Cu1A—Cu1Ai | 98.53 (15) |
Cu2—S1—C1—C2 | 174.73 (18) | Ni—S2—Cu1A—Cu1Ai | −165.54 (9) |
Cu1—S1—C1—C2 | −43.5 (3) | Cu1i—S2—Cu1A—Cu1Ai | −12.65 (14) |
Cu1A—S1—C1—C2 | −27.7 (3) | C10—S2—Cu1A—Ni | −95.93 (12) |
Ni—S1—C1—C12 | 151.5 (2) | Cu1i—S2—Cu1A—Ni | 152.88 (11) |
Cu2—S1—C1—C12 | −66.6 (3) | Cu1Ai—S2—Cu1A—Ni | 165.54 (9) |
Cu1—S1—C1—C12 | 75.2 (3) | C10—S2—Cu1A—S1 | −143.89 (12) |
Cu1A—S1—C1—C12 | 91.0 (3) | Ni—S2—Cu1A—S1 | −47.96 (7) |
Ni—S1—C1—C11 | −87.5 (2) | Cu1i—S2—Cu1A—S1 | 104.93 (10) |
Cu2—S1—C1—C11 | 54.4 (3) | Cu1Ai—S2—Cu1A—S1 | 117.58 (14) |
Cu1—S1—C1—C11 | −163.83 (19) | C10—S2—Cu1A—Cu1i | 111.18 (10) |
Cu1A—S1—C1—C11 | −148.0 (3) | Ni—S2—Cu1A—Cu1i | −152.88 (11) |
C8—N2—C9—C10 | 179.5 (3) | Cu1Ai—S2—Cu1A—Cu1i | 12.65 (14) |
Symmetry code: (i) −x, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O20ii | 0.84 (4) | 2.13 (4) | 2.921 (5) | 157 (3) |
N2—H2N···Cl1 | 0.92 (4) | 2.57 (4) | 3.359 (3) | 144 (3) |
C9—H9B···Cl2iii | 0.97 | 2.67 | 3.552 (4) | 151 |
Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x+1/2, y−1/2, z. |
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