The structural motif of piperidinium bis[
N-(2-hydroxynaphthalen-1-yl)sarcosinato]cobaltate(III), (C
5H
10NH
2)[Co(C
14H
13NO
3)
2], (I), displays a chain of two alternating discrete mononuclear Co
III complex anions with intervening piperidinium counter-ions. The piperidinium cations and complex anions interact
via N—H
O hydrogen bonding. Each of the tridentate ligands coordinates to the Co atom in a facial mode, giving a pseudo-octahedral geometry consistent with the mixed donor-atom environment, and each complex anion exhibits C
i symmetry about the metal centre. The average Co
III—O
naphtholate distance in (I) lies within the observed range of normal values for Co
III—O
phenolate distances in related compounds, indicative of similarity of coordination behaviour between the naphtholate and phenolate moieties.
Supporting information
CCDC reference: 193723
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.102
- Data-to-parameter ratio = 18.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXTL.
Crystal data top
(C5H12N)[Co(C14H13NO3)2] | Z = 2 |
Mr = 631.59 | F(000) = 664 |
Triclinic, P1 | Dx = 1.388 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.130 (2) Å | Cell parameters from 965 reflections |
b = 11.778 (2) Å | θ = 2.5–25.8° |
c = 13.065 (3) Å | µ = 0.62 mm−1 |
α = 99.608 (4)° | T = 293 K |
β = 90.336 (5)° | Plate, dark red |
γ = 100.351 (4)° | 0.18 × 0.18 × 0.02 mm |
V = 1510.8 (5) Å3 | |
Data collection top
Bruker SMART 1K CCD diffractometer | 7345 independent reflections |
Radiation source: fine-focus sealed tube | 4286 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
ω scans | θmax = 28.3°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→10 |
Tmin = 0.866, Tmax = 0.988 | k = −15→15 |
10784 measured reflections | l = −13→17 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0433P)2] where P = (Fo2 + 2Fc2)/3 |
7345 reflections | (Δ/σ)max < 0.001 |
392 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.35 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. The crystal structure was solved by direct methods. Non-hydrogen atoms were
first refined isotropically followed by anisotropic refinement by full matrix
least-squares calculation based on F2. Hydrogen atoms were positioned
geometrically and allowed to ride on their respective parent atoms. 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 | |
Co1 | 0.5000 | 0.5000 | 0.0000 | 0.03210 (13) | |
Co2 | 1.0000 | 0.0000 | 0.0000 | 0.03259 (13) | |
N1 | 0.52068 (19) | 0.67069 (15) | 0.05492 (15) | 0.0333 (5) | |
N3 | −0.0514 (2) | 0.43878 (17) | 0.14092 (16) | 0.0442 (5) | |
H3A | −0.0716 | 0.3930 | 0.0785 | 0.053* | |
H3B | −0.0798 | 0.5066 | 0.1391 | 0.053* | |
N1' | 1.0848 (2) | 0.00669 (16) | 0.13937 (14) | 0.0344 (5) | |
O1 | 0.41735 (17) | 0.45598 (13) | 0.12239 (13) | 0.0404 (4) | |
O2 | 0.67372 (16) | 0.50953 (13) | 0.06079 (12) | 0.0375 (4) | |
O3 | 0.84844 (18) | 0.63830 (15) | 0.13790 (16) | 0.0541 (5) | |
O1' | 0.82220 (16) | −0.03795 (13) | 0.04718 (12) | 0.0376 (4) | |
O2' | 1.01584 (17) | −0.16147 (13) | −0.01968 (12) | 0.0371 (4) | |
O3' | 1.13613 (19) | −0.28116 (15) | 0.03653 (14) | 0.0491 (5) | |
C1 | 0.4992 (3) | 0.6328 (2) | 0.23650 (19) | 0.0394 (6) | |
C2 | 0.4744 (3) | 0.5118 (2) | 0.2130 (2) | 0.0401 (6) | |
C3 | 0.5113 (3) | 0.4465 (3) | 0.2878 (2) | 0.0541 (8) | |
H3 | 0.4921 | 0.3650 | 0.2741 | 0.065* | |
C4 | 0.5745 (3) | 0.5028 (3) | 0.3792 (2) | 0.0616 (9) | |
H4 | 0.5976 | 0.4588 | 0.4270 | 0.074* | |
C5 | 0.6060 (3) | 0.6263 (3) | 0.4036 (2) | 0.0540 (8) | |
C6 | 0.6755 (3) | 0.6850 (4) | 0.4977 (2) | 0.0776 (11) | |
H6 | 0.7024 | 0.6417 | 0.5447 | 0.093* | |
C7 | 0.7029 (4) | 0.8032 (4) | 0.5193 (3) | 0.0910 (13) | |
H7 | 0.7492 | 0.8406 | 0.5809 | 0.109* | |
C8 | 0.6624 (4) | 0.8697 (3) | 0.4503 (3) | 0.0876 (13) | |
H8 | 0.6804 | 0.9510 | 0.4668 | 0.105* | |
C9 | 0.5971 (3) | 0.8167 (3) | 0.3592 (2) | 0.0654 (9) | |
H9 | 0.5716 | 0.8627 | 0.3140 | 0.079* | |
C10 | 0.5665 (3) | 0.6931 (2) | 0.3311 (2) | 0.0464 (7) | |
C11 | 0.4503 (3) | 0.6919 (2) | 0.15499 (19) | 0.0383 (6) | |
H11A | 0.4638 | 0.7755 | 0.1804 | 0.046* | |
H11B | 0.3547 | 0.6637 | 0.1421 | 0.046* | |
C12 | 0.7360 (3) | 0.6146 (2) | 0.0945 (2) | 0.0380 (6) | |
C13 | 0.6678 (2) | 0.7120 (2) | 0.0730 (2) | 0.0405 (6) | |
H13A | 0.6842 | 0.7759 | 0.1315 | 0.049* | |
H13B | 0.7054 | 0.7412 | 0.0122 | 0.049* | |
C14 | 0.4689 (3) | 0.7390 (2) | −0.0176 (2) | 0.0420 (6) | |
H14A | 0.3740 | 0.7122 | −0.0298 | 0.063* | |
H14B | 0.5134 | 0.7282 | −0.0822 | 0.063* | |
H14C | 0.4859 | 0.8206 | 0.0125 | 0.063* | |
C100 | −0.1248 (3) | 0.3802 (2) | 0.2213 (2) | 0.0558 (8) | |
H10B | −0.1026 | 0.3031 | 0.2184 | 0.067* | |
H10A | −0.2207 | 0.3706 | 0.2074 | 0.067* | |
C101 | −0.0893 (3) | 0.4505 (3) | 0.3278 (2) | 0.0648 (9) | |
H10D | −0.1331 | 0.4077 | 0.3793 | 0.078* | |
H10C | −0.1217 | 0.5239 | 0.3334 | 0.078* | |
C102 | 0.0611 (3) | 0.4755 (3) | 0.3493 (2) | 0.0722 (10) | |
H10E | 0.0821 | 0.5252 | 0.4165 | 0.087* | |
H10F | 0.0924 | 0.4027 | 0.3511 | 0.087* | |
C103 | 0.1321 (3) | 0.5356 (3) | 0.2659 (2) | 0.0619 (8) | |
H10G | 0.1069 | 0.6117 | 0.2686 | 0.074* | |
H10H | 0.2284 | 0.5478 | 0.2788 | 0.074* | |
C104 | 0.0963 (3) | 0.4635 (2) | 0.1591 (2) | 0.0504 (7) | |
H10I | 0.1385 | 0.5060 | 0.1067 | 0.061* | |
H10J | 0.1294 | 0.3905 | 0.1537 | 0.061* | |
C1' | 0.8691 (3) | 0.0334 (2) | 0.22648 (19) | 0.0382 (6) | |
C2' | 0.7879 (3) | 0.0182 (2) | 0.13762 (19) | 0.0367 (6) | |
C3' | 0.6642 (3) | 0.0579 (2) | 0.1440 (2) | 0.0463 (7) | |
H3' | 0.6086 | 0.0463 | 0.0849 | 0.056* | |
C4' | 0.6252 (3) | 0.1133 (2) | 0.2364 (2) | 0.0527 (7) | |
H4' | 0.5424 | 0.1371 | 0.2392 | 0.063* | |
C5' | 0.7076 (3) | 0.1351 (2) | 0.3274 (2) | 0.0491 (7) | |
C6' | 0.6693 (4) | 0.1942 (3) | 0.4230 (3) | 0.0645 (9) | |
H6' | 0.5869 | 0.2186 | 0.4265 | 0.077* | |
C7' | 0.7509 (4) | 0.2157 (3) | 0.5096 (3) | 0.0740 (10) | |
H7' | 0.7238 | 0.2543 | 0.5717 | 0.089* | |
C8' | 0.8752 (4) | 0.1802 (3) | 0.5054 (2) | 0.0724 (10) | |
H8' | 0.9317 | 0.1973 | 0.5645 | 0.087* | |
C9' | 0.9148 (3) | 0.1202 (2) | 0.4151 (2) | 0.0568 (8) | |
H9' | 0.9967 | 0.0949 | 0.4144 | 0.068* | |
C10' | 0.8327 (3) | 0.0959 (2) | 0.3227 (2) | 0.0445 (7) | |
C11' | 0.9832 (3) | −0.0320 (2) | 0.21562 (19) | 0.0418 (6) | |
H11C | 0.9474 | −0.1147 | 0.1940 | 0.050* | |
H11D | 1.0282 | −0.0225 | 0.2831 | 0.050* | |
C12' | 1.1038 (3) | −0.1847 (2) | 0.04149 (19) | 0.0374 (6) | |
C13' | 1.1721 (3) | −0.0823 (2) | 0.12118 (18) | 0.0400 (6) | |
H13C | 1.1885 | −0.1089 | 0.1857 | 0.048* | |
H13D | 1.2578 | −0.0484 | 0.0963 | 0.048* | |
C14' | 1.1652 (3) | 0.1232 (2) | 0.18172 (19) | 0.0459 (7) | |
H14F | 1.2190 | 0.1172 | 0.2407 | 0.069* | |
H14D | 1.1062 | 0.1774 | 0.2026 | 0.069* | |
H14E | 1.2227 | 0.1504 | 0.1293 | 0.069* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.0266 (3) | 0.0298 (2) | 0.0411 (3) | 0.0041 (2) | 0.0018 (2) | 0.0104 (2) |
Co2 | 0.0352 (3) | 0.0300 (2) | 0.0315 (3) | 0.0033 (2) | −0.0018 (2) | 0.0053 (2) |
N1 | 0.0285 (12) | 0.0309 (10) | 0.0428 (12) | 0.0068 (9) | 0.0012 (9) | 0.0109 (9) |
N3 | 0.0471 (15) | 0.0379 (12) | 0.0479 (14) | 0.0102 (10) | −0.0017 (11) | 0.0058 (10) |
N1' | 0.0344 (12) | 0.0362 (11) | 0.0313 (11) | 0.0049 (9) | 0.0010 (9) | 0.0038 (9) |
O1 | 0.0396 (11) | 0.0353 (9) | 0.0457 (11) | 0.0012 (8) | 0.0060 (8) | 0.0112 (8) |
O2 | 0.0312 (10) | 0.0346 (9) | 0.0486 (11) | 0.0069 (8) | 0.0016 (8) | 0.0119 (8) |
O3 | 0.0308 (11) | 0.0448 (11) | 0.0861 (15) | 0.0032 (8) | −0.0125 (10) | 0.0137 (10) |
O1' | 0.0357 (10) | 0.0379 (9) | 0.0356 (10) | 0.0000 (8) | 0.0001 (7) | 0.0035 (8) |
O2' | 0.0415 (11) | 0.0331 (9) | 0.0362 (10) | 0.0071 (8) | −0.0031 (8) | 0.0044 (7) |
O3' | 0.0515 (13) | 0.0433 (10) | 0.0561 (12) | 0.0198 (9) | 0.0016 (9) | 0.0070 (9) |
C1 | 0.0336 (15) | 0.0437 (15) | 0.0408 (15) | 0.0035 (12) | 0.0030 (11) | 0.0108 (12) |
C2 | 0.0303 (15) | 0.0478 (15) | 0.0445 (16) | 0.0060 (12) | 0.0106 (12) | 0.0155 (13) |
C3 | 0.063 (2) | 0.0557 (17) | 0.0544 (19) | 0.0219 (15) | 0.0152 (15) | 0.0273 (15) |
C4 | 0.065 (2) | 0.088 (2) | 0.0464 (19) | 0.0326 (19) | 0.0091 (15) | 0.0327 (17) |
C5 | 0.0418 (18) | 0.079 (2) | 0.0443 (17) | 0.0115 (16) | 0.0055 (13) | 0.0199 (15) |
C6 | 0.055 (2) | 0.130 (3) | 0.048 (2) | 0.000 (2) | −0.0022 (16) | 0.031 (2) |
C7 | 0.070 (3) | 0.132 (4) | 0.050 (2) | −0.031 (3) | −0.0085 (18) | 0.009 (2) |
C8 | 0.100 (3) | 0.091 (3) | 0.049 (2) | −0.038 (2) | 0.0002 (19) | 0.0053 (19) |
C9 | 0.074 (2) | 0.065 (2) | 0.0461 (18) | −0.0141 (17) | −0.0006 (16) | 0.0066 (15) |
C10 | 0.0372 (16) | 0.0592 (17) | 0.0403 (16) | −0.0014 (13) | 0.0060 (12) | 0.0118 (13) |
C11 | 0.0340 (15) | 0.0373 (13) | 0.0450 (16) | 0.0121 (11) | 0.0040 (11) | 0.0050 (12) |
C12 | 0.0304 (15) | 0.0385 (14) | 0.0469 (16) | 0.0059 (12) | 0.0064 (12) | 0.0128 (12) |
C13 | 0.0305 (15) | 0.0327 (13) | 0.0584 (17) | 0.0010 (11) | 0.0009 (12) | 0.0132 (12) |
C14 | 0.0463 (17) | 0.0322 (13) | 0.0514 (17) | 0.0102 (12) | −0.0022 (13) | 0.0156 (12) |
C100 | 0.0408 (18) | 0.0582 (18) | 0.068 (2) | 0.0001 (14) | 0.0066 (14) | 0.0179 (16) |
C101 | 0.056 (2) | 0.081 (2) | 0.055 (2) | 0.0011 (17) | 0.0165 (15) | 0.0136 (17) |
C102 | 0.065 (2) | 0.100 (3) | 0.050 (2) | 0.013 (2) | −0.0070 (16) | 0.0109 (18) |
C103 | 0.0382 (18) | 0.082 (2) | 0.058 (2) | 0.0010 (16) | 0.0028 (14) | 0.0013 (17) |
C104 | 0.0391 (17) | 0.0549 (17) | 0.0579 (19) | 0.0097 (14) | 0.0077 (13) | 0.0102 (14) |
C1' | 0.0387 (16) | 0.0374 (13) | 0.0392 (15) | 0.0048 (12) | 0.0065 (12) | 0.0103 (11) |
C2' | 0.0380 (16) | 0.0310 (13) | 0.0410 (15) | 0.0015 (11) | 0.0039 (11) | 0.0114 (11) |
C3' | 0.0404 (17) | 0.0442 (15) | 0.0566 (18) | 0.0076 (13) | 0.0015 (13) | 0.0156 (14) |
C4' | 0.0461 (19) | 0.0457 (16) | 0.071 (2) | 0.0163 (14) | 0.0133 (15) | 0.0153 (15) |
C5' | 0.054 (2) | 0.0403 (15) | 0.0527 (18) | 0.0079 (14) | 0.0159 (14) | 0.0071 (13) |
C6' | 0.069 (2) | 0.0537 (19) | 0.070 (2) | 0.0138 (17) | 0.0298 (18) | 0.0057 (17) |
C7' | 0.086 (3) | 0.067 (2) | 0.058 (2) | 0.003 (2) | 0.0265 (19) | −0.0087 (17) |
C8' | 0.075 (3) | 0.083 (2) | 0.045 (2) | −0.004 (2) | 0.0095 (17) | −0.0076 (17) |
C9' | 0.054 (2) | 0.0669 (19) | 0.0427 (17) | 0.0004 (15) | 0.0062 (14) | 0.0022 (15) |
C10' | 0.0498 (18) | 0.0398 (14) | 0.0417 (16) | 0.0019 (13) | 0.0109 (13) | 0.0074 (12) |
C11' | 0.0467 (17) | 0.0476 (15) | 0.0306 (14) | 0.0051 (13) | −0.0005 (12) | 0.0096 (12) |
C12' | 0.0347 (15) | 0.0408 (14) | 0.0386 (15) | 0.0092 (12) | 0.0068 (11) | 0.0094 (12) |
C13' | 0.0390 (16) | 0.0457 (15) | 0.0370 (15) | 0.0103 (12) | −0.0038 (11) | 0.0090 (12) |
C14' | 0.0499 (18) | 0.0426 (15) | 0.0389 (15) | −0.0004 (13) | −0.0065 (13) | −0.0014 (12) |
Geometric parameters (Å, º) top
Co1—O2i | 1.9033 (16) | C11—H11B | 0.9700 |
Co1—O2 | 1.9033 (16) | C12—C13 | 1.503 (3) |
Co1—O1i | 1.9139 (17) | C13—H13A | 0.9700 |
Co1—O1 | 1.9139 (17) | C13—H13B | 0.9700 |
Co1—N1 | 1.9915 (18) | C14—H14A | 0.9600 |
Co1—N1i | 1.9915 (18) | C14—H14B | 0.9600 |
Co2—O1'ii | 1.9076 (17) | C14—H14C | 0.9600 |
Co2—O1' | 1.9076 (17) | C100—C101 | 1.501 (4) |
Co2—O2'ii | 1.9120 (15) | C100—H10B | 0.9700 |
Co2—O2' | 1.9120 (15) | C100—H10A | 0.9700 |
Co2—N1'ii | 1.9922 (18) | C101—C102 | 1.514 (4) |
Co2—N1' | 1.9922 (18) | C101—H10D | 0.9700 |
N1—C13 | 1.486 (3) | C101—H10C | 0.9700 |
N1—C14 | 1.490 (3) | C102—C103 | 1.513 (4) |
N1—C11 | 1.499 (3) | C102—H10E | 0.9700 |
N3—C104 | 1.482 (3) | C102—H10F | 0.9700 |
N3—C100 | 1.483 (3) | C103—C104 | 1.513 (4) |
N3—H3A | 0.9000 | C103—H10G | 0.9700 |
N3—H3B | 0.9000 | C103—H10H | 0.9700 |
N1'—C13' | 1.480 (3) | C104—H10I | 0.9700 |
N1'—C14' | 1.481 (3) | C104—H10J | 0.9700 |
N1'—C11' | 1.501 (3) | C1'—C2' | 1.387 (3) |
O1—C2 | 1.328 (3) | C1'—C10' | 1.433 (3) |
O2—C12 | 1.288 (3) | C1'—C11' | 1.496 (3) |
O3—C12 | 1.234 (3) | C2'—C3' | 1.412 (3) |
O1'—C2' | 1.335 (3) | C3'—C4' | 1.369 (4) |
O2'—C12' | 1.288 (3) | C3'—H3' | 0.9300 |
O3'—C12' | 1.230 (3) | C4'—C5' | 1.410 (4) |
C1—C2 | 1.384 (3) | C4'—H4' | 0.9300 |
C1—C10 | 1.421 (3) | C5'—C6' | 1.416 (4) |
C1—C11 | 1.493 (3) | C5'—C10' | 1.422 (4) |
C2—C3 | 1.427 (3) | C6'—C7' | 1.358 (4) |
C3—C4 | 1.359 (4) | C6'—H6' | 0.9300 |
C3—H3 | 0.9300 | C7'—C8' | 1.395 (5) |
C4—C5 | 1.412 (4) | C7'—H7' | 0.9300 |
C4—H4 | 0.9300 | C8'—C9' | 1.372 (4) |
C5—C6 | 1.420 (4) | C8'—H8' | 0.9300 |
C5—C10 | 1.426 (4) | C9'—C10' | 1.421 (4) |
C6—C7 | 1.350 (5) | C9'—H9' | 0.9300 |
C6—H6 | 0.9300 | C11'—H11C | 0.9700 |
C7—C8 | 1.394 (5) | C11'—H11D | 0.9700 |
C7—H7 | 0.9300 | C12'—C13' | 1.513 (3) |
C8—C9 | 1.356 (4) | C13'—H13C | 0.9700 |
C8—H8 | 0.9300 | C13'—H13D | 0.9700 |
C9—C10 | 1.417 (4) | C14'—H14F | 0.9600 |
C9—H9 | 0.9300 | C14'—H14D | 0.9600 |
C11—H11A | 0.9700 | C14'—H14E | 0.9600 |
| | | |
O2i—Co1—O2 | 180.00 (11) | N1—C13—H13A | 109.4 |
O2i—Co1—O1i | 90.86 (7) | C12—C13—H13A | 109.4 |
O2—Co1—O1i | 89.14 (7) | N1—C13—H13B | 109.4 |
O2i—Co1—O1 | 89.14 (7) | C12—C13—H13B | 109.4 |
O2—Co1—O1 | 90.86 (7) | H13A—C13—H13B | 108.0 |
O1i—Co1—O1 | 180.0 | N1—C14—H14A | 109.5 |
O2i—Co1—N1 | 93.57 (7) | N1—C14—H14B | 109.5 |
O2—Co1—N1 | 86.43 (7) | H14A—C14—H14B | 109.5 |
O1i—Co1—N1 | 86.67 (7) | N1—C14—H14C | 109.5 |
O1—Co1—N1 | 93.33 (7) | H14A—C14—H14C | 109.5 |
O2i—Co1—N1i | 86.43 (7) | H14B—C14—H14C | 109.5 |
O2—Co1—N1i | 93.57 (7) | N3—C100—C101 | 111.0 (2) |
O1i—Co1—N1i | 93.33 (7) | N3—C100—H10B | 109.4 |
O1—Co1—N1i | 86.67 (7) | C101—C100—H10B | 109.4 |
N1—Co1—N1i | 180.0 | N3—C100—H10A | 109.4 |
O1'ii—Co2—O1' | 180.00 (9) | C101—C100—H10A | 109.4 |
O1'ii—Co2—O2'ii | 90.42 (7) | H10B—C100—H10A | 108.0 |
O1'—Co2—O2'ii | 89.58 (7) | C100—C101—C102 | 111.1 (3) |
O1'ii—Co2—O2' | 89.58 (7) | C100—C101—H10D | 109.4 |
O1'—Co2—O2' | 90.42 (7) | C102—C101—H10D | 109.4 |
O2'ii—Co2—O2' | 180.00 (10) | C100—C101—H10C | 109.4 |
O1'ii—Co2—N1'ii | 93.34 (8) | C102—C101—H10C | 109.4 |
O1'—Co2—N1'ii | 86.66 (8) | H10D—C101—H10C | 108.0 |
O2'ii—Co2—N1'ii | 84.10 (7) | C103—C102—C101 | 110.3 (2) |
O2'—Co2—N1'ii | 95.90 (7) | C103—C102—H10E | 109.6 |
O1'ii—Co2—N1' | 86.66 (8) | C101—C102—H10E | 109.6 |
O1'—Co2—N1' | 93.34 (8) | C103—C102—H10F | 109.6 |
O2'ii—Co2—N1' | 95.90 (7) | C101—C102—H10F | 109.6 |
O2'—Co2—N1' | 84.10 (7) | H10E—C102—H10F | 108.1 |
N1'ii—Co2—N1' | 180.00 (5) | C104—C103—C102 | 111.2 (3) |
C13—N1—C14 | 109.24 (18) | C104—C103—H10G | 109.4 |
C13—N1—C11 | 110.05 (19) | C102—C103—H10G | 109.4 |
C14—N1—C11 | 107.54 (19) | C104—C103—H10H | 109.4 |
C13—N1—Co1 | 104.84 (14) | C102—C103—H10H | 109.4 |
C14—N1—Co1 | 114.10 (15) | H10G—C103—H10H | 108.0 |
C11—N1—Co1 | 111.05 (14) | N3—C104—C103 | 109.8 (2) |
C104—N3—C100 | 113.4 (2) | N3—C104—H10I | 109.7 |
C104—N3—H3A | 108.9 | C103—C104—H10I | 109.7 |
C100—N3—H3A | 108.9 | N3—C104—H10J | 109.7 |
C104—N3—H3B | 108.9 | C103—C104—H10J | 109.7 |
C100—N3—H3B | 108.9 | H10I—C104—H10J | 108.2 |
H3A—N3—H3B | 107.7 | C2'—C1'—C10' | 120.5 (3) |
C13'—N1'—C14' | 110.41 (19) | C2'—C1'—C11' | 114.8 (2) |
C13'—N1'—C11' | 106.75 (18) | C10'—C1'—C11' | 124.2 (2) |
C14'—N1'—C11' | 110.54 (19) | O1'—C2'—C1' | 120.9 (2) |
C13'—N1'—Co2 | 103.87 (13) | O1'—C2'—C3' | 119.6 (2) |
C14'—N1'—Co2 | 113.08 (14) | C1'—C2'—C3' | 119.5 (2) |
C11'—N1'—Co2 | 111.81 (15) | C4'—C3'—C2' | 120.7 (3) |
C2—O1—Co1 | 116.88 (15) | C4'—C3'—H3' | 119.6 |
C12—O2—Co1 | 114.45 (15) | C2'—C3'—H3' | 119.6 |
C2'—O1'—Co2 | 120.15 (14) | C3'—C4'—C5' | 121.5 (3) |
C12'—O2'—Co2 | 114.27 (15) | C3'—C4'—H4' | 119.2 |
C2—C1—C10 | 121.3 (2) | C5'—C4'—H4' | 119.2 |
C2—C1—C11 | 114.5 (2) | C4'—C5'—C6' | 122.0 (3) |
C10—C1—C11 | 124.2 (2) | C4'—C5'—C10' | 118.7 (3) |
O1—C2—C1 | 121.1 (2) | C6'—C5'—C10' | 119.3 (3) |
O1—C2—C3 | 119.8 (2) | C7'—C6'—C5' | 121.2 (3) |
C1—C2—C3 | 119.1 (2) | C7'—C6'—H6' | 119.4 |
C4—C3—C2 | 120.2 (3) | C5'—C6'—H6' | 119.4 |
C4—C3—H3 | 119.9 | C6'—C7'—C8' | 120.1 (3) |
C2—C3—H3 | 119.9 | C6'—C7'—H7' | 119.9 |
C3—C4—C5 | 122.0 (3) | C8'—C7'—H7' | 119.9 |
C3—C4—H4 | 119.0 | C9'—C8'—C7' | 120.6 (3) |
C5—C4—H4 | 119.0 | C9'—C8'—H8' | 119.7 |
C4—C5—C6 | 121.9 (3) | C7'—C8'—H8' | 119.7 |
C4—C5—C10 | 118.6 (3) | C8'—C9'—C10' | 121.1 (3) |
C6—C5—C10 | 119.5 (3) | C8'—C9'—H9' | 119.5 |
C7—C6—C5 | 120.5 (3) | C10'—C9'—H9' | 119.5 |
C7—C6—H6 | 119.8 | C9'—C10'—C5' | 117.7 (3) |
C5—C6—H6 | 119.8 | C9'—C10'—C1' | 123.3 (3) |
C6—C7—C8 | 120.7 (3) | C5'—C10'—C1' | 119.0 (2) |
C6—C7—H7 | 119.6 | C1'—C11'—N1' | 114.11 (19) |
C8—C7—H7 | 119.6 | C1'—C11'—H11C | 108.7 |
C9—C8—C7 | 120.4 (3) | N1'—C11'—H11C | 108.7 |
C9—C8—H8 | 119.8 | C1'—C11'—H11D | 108.7 |
C7—C8—H8 | 119.8 | N1'—C11'—H11D | 108.7 |
C8—C9—C10 | 121.8 (3) | H11C—C11'—H11D | 107.6 |
C8—C9—H9 | 119.1 | O3'—C12'—O2' | 124.5 (2) |
C10—C9—H9 | 119.1 | O3'—C12'—C13' | 120.0 (2) |
C9—C10—C1 | 124.2 (2) | O2'—C12'—C13' | 115.5 (2) |
C9—C10—C5 | 117.1 (3) | N1'—C13'—C12' | 109.16 (19) |
C1—C10—C5 | 118.7 (3) | N1'—C13'—H13C | 109.8 |
C1—C11—N1 | 112.7 (2) | C12'—C13'—H13C | 109.8 |
C1—C11—H11A | 109.1 | N1'—C13'—H13D | 109.8 |
N1—C11—H11A | 109.1 | C12'—C13'—H13D | 109.8 |
C1—C11—H11B | 109.1 | H13C—C13'—H13D | 108.3 |
N1—C11—H11B | 109.1 | N1'—C14'—H14F | 109.5 |
H11A—C11—H11B | 107.8 | N1'—C14'—H14D | 109.5 |
O3—C12—O2 | 123.9 (2) | H14F—C14'—H14D | 109.5 |
O3—C12—C13 | 119.7 (2) | N1'—C14'—H14E | 109.5 |
O2—C12—C13 | 116.4 (2) | H14F—C14'—H14E | 109.5 |
N1—C13—C12 | 111.08 (18) | H14D—C14'—H14E | 109.5 |
| | | |
O2i—Co1—N1—C13 | −159.50 (14) | C11—C1—C10—C5 | 178.9 (3) |
O2—Co1—N1—C13 | 20.50 (14) | C4—C5—C10—C9 | 178.6 (3) |
O1i—Co1—N1—C13 | −68.85 (15) | C6—C5—C10—C9 | −1.5 (4) |
O1—Co1—N1—C13 | 111.15 (15) | C4—C5—C10—C1 | −1.1 (4) |
O2i—Co1—N1—C14 | −40.03 (17) | C6—C5—C10—C1 | 178.9 (3) |
O2—Co1—N1—C14 | 139.97 (17) | C2—C1—C11—N1 | −64.2 (3) |
O1i—Co1—N1—C14 | 50.62 (17) | C10—C1—C11—N1 | 115.5 (3) |
O1—Co1—N1—C14 | −129.38 (17) | C13—N1—C11—C1 | −58.1 (2) |
O2i—Co1—N1—C11 | 81.69 (15) | C14—N1—C11—C1 | −176.9 (2) |
O2—Co1—N1—C11 | −98.31 (15) | Co1—N1—C11—C1 | 57.6 (2) |
O1i—Co1—N1—C11 | 172.34 (15) | Co1—O2—C12—O3 | 178.6 (2) |
O1—Co1—N1—C11 | −7.66 (15) | Co1—O2—C12—C13 | −4.8 (3) |
O1'ii—Co2—N1'—C13' | −58.85 (14) | C14—N1—C13—C12 | −149.9 (2) |
O1'—Co2—N1'—C13' | 121.15 (14) | C11—N1—C13—C12 | 92.2 (2) |
O2'ii—Co2—N1'—C13' | −148.93 (14) | Co1—N1—C13—C12 | −27.2 (2) |
O2'—Co2—N1'—C13' | 31.07 (14) | O3—C12—C13—N1 | −160.6 (2) |
O1'ii—Co2—N1'—C14' | 60.86 (17) | O2—C12—C13—N1 | 22.8 (3) |
O1'—Co2—N1'—C14' | −119.14 (17) | C104—N3—C100—C101 | 55.8 (3) |
O2'ii—Co2—N1'—C14' | −29.22 (18) | N3—C100—C101—C102 | −54.7 (3) |
O2'—Co2—N1'—C14' | 150.78 (18) | C100—C101—C102—C103 | 55.6 (4) |
O1'ii—Co2—N1'—C11' | −173.60 (16) | C101—C102—C103—C104 | −56.4 (4) |
O1'—Co2—N1'—C11' | 6.40 (16) | C100—N3—C104—C103 | −55.9 (3) |
O2'ii—Co2—N1'—C11' | 96.32 (16) | C102—C103—C104—N3 | 55.9 (3) |
O2'—Co2—N1'—C11' | −83.68 (16) | Co2—O1'—C2'—C1' | −47.4 (3) |
O2i—Co1—O1—C2 | −139.14 (17) | Co2—O1'—C2'—C3' | 135.55 (19) |
O2—Co1—O1—C2 | 40.86 (17) | C10'—C1'—C2'—O1' | 178.7 (2) |
N1—Co1—O1—C2 | −45.62 (17) | C11'—C1'—C2'—O1' | −8.6 (3) |
N1i—Co1—O1—C2 | 134.38 (17) | C10'—C1'—C2'—C3' | −4.3 (3) |
O1i—Co1—O2—C12 | 77.07 (17) | C11'—C1'—C2'—C3' | 168.4 (2) |
O1—Co1—O2—C12 | −102.93 (17) | O1'—C2'—C3'—C4' | 178.5 (2) |
N1—Co1—O2—C12 | −9.65 (17) | C1'—C2'—C3'—C4' | 1.4 (4) |
N1i—Co1—O2—C12 | 170.35 (17) | C2'—C3'—C4'—C5' | 1.5 (4) |
O2'ii—Co2—O1'—C2' | −52.47 (17) | C3'—C4'—C5'—C6' | 178.9 (3) |
O2'—Co2—O1'—C2' | 127.53 (17) | C3'—C4'—C5'—C10' | −1.4 (4) |
N1'ii—Co2—O1'—C2' | −136.58 (17) | C4'—C5'—C6'—C7' | −179.1 (3) |
N1'—Co2—O1'—C2' | 43.42 (17) | C10'—C5'—C6'—C7' | 1.1 (4) |
O1'ii—Co2—O2'—C12' | 66.14 (18) | C5'—C6'—C7'—C8' | 0.3 (5) |
O1'—Co2—O2'—C12' | −113.86 (18) | C6'—C7'—C8'—C9' | −2.0 (5) |
N1'ii—Co2—O2'—C12' | 159.45 (17) | C7'—C8'—C9'—C10' | 2.1 (5) |
N1'—Co2—O2'—C12' | −20.55 (17) | C8'—C9'—C10'—C5' | −0.6 (4) |
Co1—O1—C2—C1 | 53.8 (3) | C8'—C9'—C10'—C1' | −179.9 (3) |
Co1—O1—C2—C3 | −126.1 (2) | C4'—C5'—C10'—C9' | 179.3 (2) |
C10—C1—C2—O1 | −176.7 (2) | C6'—C5'—C10'—C9' | −1.0 (4) |
C11—C1—C2—O1 | 3.0 (4) | C4'—C5'—C10'—C1' | −1.5 (4) |
C10—C1—C2—C3 | 3.2 (4) | C6'—C5'—C10'—C1' | 178.3 (2) |
C11—C1—C2—C3 | −177.0 (2) | C2'—C1'—C10'—C9' | −176.5 (2) |
O1—C2—C3—C4 | 177.5 (3) | C11'—C1'—C10'—C9' | 11.5 (4) |
C1—C2—C3—C4 | −2.5 (4) | C2'—C1'—C10'—C5' | 4.3 (4) |
C2—C3—C4—C5 | −0.1 (5) | C11'—C1'—C10'—C5' | −167.7 (2) |
C3—C4—C5—C6 | −178.1 (3) | C2'—C1'—C11'—N1' | 64.3 (3) |
C3—C4—C5—C10 | 1.9 (5) | C10'—C1'—C11'—N1' | −123.3 (2) |
C4—C5—C6—C7 | −179.2 (3) | C13'—N1'—C11'—C1' | −167.81 (19) |
C10—C5—C6—C7 | 0.8 (5) | C14'—N1'—C11'—C1' | 72.1 (3) |
C5—C6—C7—C8 | 0.6 (6) | Co2—N1'—C11'—C1' | −54.9 (2) |
C6—C7—C8—C9 | −1.3 (6) | Co2—O2'—C12'—O3' | −174.6 (2) |
C7—C8—C9—C10 | 0.5 (6) | Co2—O2'—C12'—C13' | 3.4 (3) |
C8—C9—C10—C1 | −179.5 (3) | C14'—N1'—C13'—C12' | −157.6 (2) |
C8—C9—C10—C5 | 0.8 (5) | C11'—N1'—C13'—C12' | 82.2 (2) |
C2—C1—C10—C9 | 178.9 (3) | Co2—N1'—C13'—C12' | −36.1 (2) |
C11—C1—C10—C9 | −0.8 (4) | O3'—C12'—C13'—N1' | −158.5 (2) |
C2—C1—C10—C5 | −1.5 (4) | O2'—C12'—C13'—N1' | 23.5 (3) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3′iii | 0.90 | 1.85 | 2.743 (3) | 169 |
N3—H3B···O3iv | 0.90 | 1.83 | 2.728 (3) | 175 |
Symmetry codes: (iii) −x+1, −y, −z; (iv) x−1, y, z. |