metal-organic compounds
The Co atom in the title compound, [Co(C20H38N4O4)]·4H2O, is chelated by the four N atoms of the macrocycle and also covalently bonded to two carboxylate O atoms in a cis-N4O2Co octahedral environment. The mononuclear molecule interacts with the non-coordinated water molecules by way of O—HO interactions to form a three-dimensional network.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020532/hb6232sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020532/hb6232Isup2.hkl |
CCDC reference: 282363
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
(5,5,7,12,12,14-Hexamethyl-1,4,8,11-tetraazacyclotetradecane-1,8-
diacetato)cobalt(II) tetrahydrate top
Crystal data top
[Co(C20H38N4O4)]·4H2O | F(000) = 1140 |
Mr = 529.54 | Dx = 1.382 Mg m−3 Dm = 1.382 Mg m−3 Dm measured by flotation in CH2Cl2/CHCl3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7719 reflections |
a = 9.1896 (6) Å | θ = 2.4–28.3° |
b = 13.8731 (9) Å | µ = 0.72 mm−1 |
c = 20.001 (1) Å | T = 295 K |
β = 93.641 (1)° | Prism, red |
V = 2544.7 (3) Å3 | 0.28 × 0.15 × 0.15 mm |
Z = 4 |
Data collection top
Bruker APEX CCD diffractometer | 5778 independent reflections |
Radiation source: fine-focus sealed tube | 5057 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→11 |
Tmin = 0.673, Tmax = 0.899 | k = −17→18 |
20921 measured reflections | l = −25→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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.18 | w = 1/[σ2(Fo2) + (0.05P)2 + 3.0855P] where P = (Fo2 + 2Fc2)/3 |
5778 reflections | (Δ/σ)max = 0.001 |
298 parameters | Δρmax = 0.67 e Å−3 |
24 restraints | Δρmin = −0.68 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Co1 | 0.62456 (4) | 0.39195 (3) | 0.25255 (2) | 0.02313 (13) | |
O1 | 0.5297 (3) | 0.49300 (17) | 0.31585 (12) | 0.0373 (5) | |
O2 | 0.3920 (3) | 0.6251 (2) | 0.30454 (17) | 0.0557 (8) | |
O3 | 0.7597 (3) | 0.51159 (16) | 0.23485 (12) | 0.0353 (5) | |
O4 | 0.9252 (3) | 0.59940 (18) | 0.29357 (16) | 0.0513 (7) | |
O1w | 0.5731 (5) | 0.5588 (3) | 0.45331 (19) | 0.0915 (12) | |
H1w1 | 0.5695 | 0.5337 | 0.4144 | 0.137* | |
H1w2 | 0.4889 | 0.5785 | 0.4620 | 0.137* | |
O2w | 0.8574 (7) | 0.5201 (6) | 0.5092 (4) | 0.178 (3) | |
H2w1 | 0.7684 | 0.5353 | 0.4999 | 0.267* | |
H2w2 | 0.8613 | 0.4595 | 0.5183 | 0.267* | |
O3w | 0.1255 (10) | 0.6183 (5) | 0.4054 (4) | 0.209 (4) | |
H3w1 | 0.0371 | 0.6280 | 0.3904 | 0.314* | |
H3w2 | 0.1768 | 0.6674 | 0.3920 | 0.314* | |
O4w | 0.3481 (10) | 0.7070 (7) | 0.4243 (4) | 0.221 (4) | |
H4w1 | 0.3267 | 0.7661 | 0.4369 | 0.332* | |
H4w2 | 0.3841 | 0.7169 | 0.3852 | 0.332* | |
N1 | 0.4305 (3) | 0.4248 (2) | 0.19567 (15) | 0.0354 (6) | |
N2 | 0.6995 (3) | 0.3060 (2) | 0.17511 (14) | 0.0342 (6) | |
H2n | 0.6349 | 0.2614 | 0.1697 | 0.041* | |
N3 | 0.8168 (3) | 0.35199 (18) | 0.30673 (14) | 0.0297 (6) | |
N4 | 0.5098 (3) | 0.27348 (19) | 0.28776 (14) | 0.0331 (6) | |
H4n | 0.5572 | 0.2242 | 0.2747 | 0.040* | |
C1 | 0.4460 (4) | 0.5514 (2) | 0.28267 (19) | 0.0369 (8) | |
C2 | 0.4099 (4) | 0.5286 (3) | 0.2091 (2) | 0.0434 (9) | |
H2a | 0.3096 | 0.5464 | 0.1971 | 0.052* | |
H2b | 0.4724 | 0.5662 | 0.1818 | 0.052* | |
C3 | 0.4352 (4) | 0.4017 (3) | 0.1225 (2) | 0.0461 (9) | |
H3 | 0.4230 | 0.3318 | 0.1178 | 0.055* | |
C4 | 0.3124 (5) | 0.4493 (4) | 0.0789 (2) | 0.0676 (14) | |
H4a | 0.2200 | 0.4313 | 0.0949 | 0.101* | |
H4b | 0.3173 | 0.4282 | 0.0334 | 0.101* | |
H4c | 0.3232 | 0.5180 | 0.0810 | 0.101* | |
C5 | 0.5854 (4) | 0.4270 (3) | 0.09812 (19) | 0.0478 (9) | |
H5a | 0.6200 | 0.4846 | 0.1217 | 0.057* | |
H5b | 0.5726 | 0.4434 | 0.0510 | 0.057* | |
C6 | 0.7054 (4) | 0.3503 (3) | 0.10633 (18) | 0.0437 (9) | |
C7 | 0.8520 (5) | 0.3994 (4) | 0.0976 (2) | 0.0605 (12) | |
H7a | 0.9288 | 0.3525 | 0.1025 | 0.091* | |
H7b | 0.8678 | 0.4486 | 0.1311 | 0.091* | |
H7c | 0.8514 | 0.4279 | 0.0539 | 0.091* | |
C8 | 0.6805 (6) | 0.2701 (4) | 0.0538 (2) | 0.0680 (14) | |
H8a | 0.7564 | 0.2228 | 0.0598 | 0.102* | |
H8b | 0.6816 | 0.2974 | 0.0097 | 0.102* | |
H8c | 0.5878 | 0.2401 | 0.0591 | 0.102* | |
C9 | 0.8320 (4) | 0.2545 (3) | 0.20323 (19) | 0.0390 (8) | |
H9a | 0.8946 | 0.2396 | 0.1674 | 0.047* | |
H9b | 0.8034 | 0.1942 | 0.2232 | 0.047* | |
C10 | 0.9158 (3) | 0.3153 (3) | 0.25586 (19) | 0.0363 (8) | |
H10a | 0.9927 | 0.2767 | 0.2780 | 0.044* | |
H10b | 0.9609 | 0.3693 | 0.2343 | 0.044* | |
C11 | 0.8758 (4) | 0.4434 (2) | 0.33442 (18) | 0.0351 (7) | |
H11a | 0.9793 | 0.4364 | 0.3462 | 0.042* | |
H11b | 0.8278 | 0.4597 | 0.3747 | 0.042* | |
C12 | 0.8517 (4) | 0.5244 (2) | 0.28285 (19) | 0.0353 (7) | |
C13 | 0.7915 (4) | 0.2768 (2) | 0.35952 (18) | 0.0371 (8) | |
H13 | 0.7753 | 0.2153 | 0.3362 | 0.045* | |
C14 | 0.9222 (5) | 0.2632 (3) | 0.4099 (2) | 0.0571 (11) | |
H14a | 1.0075 | 0.2489 | 0.3864 | 0.086* | |
H14b | 0.9031 | 0.2108 | 0.4395 | 0.086* | |
H14c | 0.9381 | 0.3212 | 0.4355 | 0.086* | |
C15 | 0.6528 (4) | 0.2998 (3) | 0.39473 (18) | 0.0406 (8) | |
H15a | 0.6443 | 0.3694 | 0.3978 | 0.049* | |
H15b | 0.6648 | 0.2752 | 0.4401 | 0.049* | |
C16 | 0.5079 (4) | 0.2604 (3) | 0.36264 (19) | 0.0401 (8) | |
C17 | 0.3829 (5) | 0.3151 (3) | 0.3921 (2) | 0.0564 (11) | |
H17a | 0.2916 | 0.2915 | 0.3725 | 0.085* | |
H17b | 0.3917 | 0.3826 | 0.3824 | 0.085* | |
H17c | 0.3868 | 0.3057 | 0.4397 | 0.085* | |
C18 | 0.4958 (5) | 0.1517 (3) | 0.3772 (2) | 0.0602 (12) | |
H18a | 0.4053 | 0.1276 | 0.3572 | 0.090* | |
H18b | 0.4990 | 0.1416 | 0.4248 | 0.090* | |
H18c | 0.5755 | 0.1183 | 0.3588 | 0.090* | |
C19 | 0.3679 (4) | 0.2688 (3) | 0.2477 (2) | 0.0439 (9) | |
H19a | 0.2962 | 0.2376 | 0.2739 | 0.053* | |
H19b | 0.3791 | 0.2304 | 0.2079 | 0.053* | |
C20 | 0.3139 (4) | 0.3692 (3) | 0.2274 (2) | 0.0427 (9) | |
H20a | 0.2294 | 0.3636 | 0.1961 | 0.051* | |
H20b | 0.2847 | 0.4034 | 0.2667 | 0.051* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0215 (2) | 0.0215 (2) | 0.0262 (2) | 0.00172 (15) | −0.00051 (15) | −0.00124 (16) |
O1 | 0.0409 (13) | 0.0341 (12) | 0.0370 (14) | 0.0039 (10) | 0.0040 (11) | −0.0034 (10) |
O2 | 0.0475 (16) | 0.0405 (15) | 0.079 (2) | 0.0113 (12) | 0.0054 (15) | −0.0168 (14) |
O3 | 0.0377 (12) | 0.0299 (12) | 0.0379 (14) | −0.0011 (10) | −0.0004 (10) | 0.0040 (10) |
O4 | 0.0518 (16) | 0.0300 (13) | 0.070 (2) | −0.0114 (11) | −0.0112 (14) | 0.0099 (12) |
O1w | 0.111 (3) | 0.096 (3) | 0.067 (2) | −0.014 (3) | 0.002 (2) | −0.014 (2) |
O2w | 0.141 (5) | 0.230 (7) | 0.162 (5) | 0.005 (5) | 0.005 (4) | 0.004 (5) |
O3w | 0.234 (7) | 0.165 (6) | 0.212 (6) | 0.005 (5) | −0.115 (6) | 0.001 (5) |
O4w | 0.238 (7) | 0.235 (7) | 0.192 (6) | 0.029 (6) | 0.027 (6) | −0.023 (6) |
N1 | 0.0325 (14) | 0.0357 (15) | 0.0374 (17) | 0.0049 (12) | −0.0018 (12) | −0.0041 (12) |
N2 | 0.0357 (15) | 0.0325 (14) | 0.0342 (16) | 0.0029 (12) | 0.0011 (12) | −0.0058 (11) |
N3 | 0.0293 (13) | 0.0241 (13) | 0.0352 (15) | −0.0015 (10) | −0.0028 (11) | 0.0033 (11) |
N4 | 0.0332 (14) | 0.0264 (13) | 0.0396 (16) | −0.0020 (11) | 0.0021 (12) | −0.0042 (11) |
C1 | 0.0303 (16) | 0.0307 (17) | 0.050 (2) | 0.0009 (13) | 0.0062 (15) | −0.0038 (15) |
C2 | 0.046 (2) | 0.0342 (19) | 0.049 (2) | 0.0110 (16) | −0.0024 (17) | 0.0028 (16) |
C3 | 0.046 (2) | 0.052 (2) | 0.039 (2) | 0.0108 (18) | −0.0099 (17) | −0.0040 (17) |
C4 | 0.062 (3) | 0.087 (4) | 0.051 (3) | 0.017 (3) | −0.022 (2) | 0.000 (2) |
C5 | 0.055 (2) | 0.057 (2) | 0.031 (2) | 0.0110 (19) | −0.0004 (17) | 0.0043 (17) |
C6 | 0.050 (2) | 0.053 (2) | 0.0289 (19) | 0.0094 (18) | 0.0020 (16) | −0.0057 (16) |
C7 | 0.060 (3) | 0.072 (3) | 0.051 (3) | 0.005 (2) | 0.018 (2) | 0.011 (2) |
C8 | 0.077 (3) | 0.082 (3) | 0.044 (3) | 0.015 (3) | −0.002 (2) | −0.027 (2) |
C9 | 0.0373 (18) | 0.0316 (17) | 0.048 (2) | 0.0072 (14) | 0.0053 (16) | −0.0053 (15) |
C10 | 0.0213 (14) | 0.0348 (18) | 0.052 (2) | 0.0070 (13) | −0.0031 (14) | 0.0039 (15) |
C11 | 0.0358 (17) | 0.0269 (16) | 0.041 (2) | −0.0060 (13) | −0.0080 (15) | −0.0020 (14) |
C12 | 0.0342 (17) | 0.0278 (16) | 0.044 (2) | −0.0010 (13) | 0.0039 (15) | 0.0013 (14) |
C13 | 0.0405 (18) | 0.0280 (16) | 0.042 (2) | −0.0031 (14) | −0.0069 (15) | 0.0065 (14) |
C14 | 0.057 (3) | 0.054 (2) | 0.058 (3) | −0.004 (2) | −0.017 (2) | 0.021 (2) |
C15 | 0.050 (2) | 0.0376 (19) | 0.0343 (19) | −0.0066 (16) | 0.0030 (16) | 0.0037 (15) |
C16 | 0.0429 (19) | 0.0369 (19) | 0.041 (2) | −0.0108 (15) | 0.0100 (16) | 0.0024 (15) |
C17 | 0.055 (2) | 0.061 (3) | 0.056 (3) | −0.009 (2) | 0.023 (2) | −0.003 (2) |
C18 | 0.074 (3) | 0.042 (2) | 0.065 (3) | −0.017 (2) | 0.010 (2) | 0.013 (2) |
C19 | 0.0335 (18) | 0.0392 (19) | 0.059 (2) | −0.0085 (15) | −0.0007 (17) | −0.0075 (17) |
C20 | 0.0295 (17) | 0.042 (2) | 0.056 (2) | 0.0004 (15) | −0.0031 (16) | −0.0072 (17) |
Geometric parameters (Å, º) top
Co1—N1 | 2.104 (3) | C5—H5a | 0.9700 |
Co1—N2 | 2.105 (3) | C5—H5b | 0.9700 |
Co1—N3 | 2.088 (3) | C6—C7 | 1.529 (6) |
Co1—N4 | 2.099 (3) | C6—C8 | 1.537 (6) |
Co1—O1 | 2.114 (2) | C7—H7a | 0.9600 |
Co1—O3 | 2.116 (2) | C7—H7b | 0.9600 |
O1—C1 | 1.274 (4) | C7—H7c | 0.9600 |
O2—C1 | 1.230 (4) | C8—H8a | 0.9600 |
O3—C12 | 1.251 (4) | C8—H8b | 0.9600 |
O4—C12 | 1.252 (4) | C8—H8c | 0.9600 |
O1w—H1w1 | 0.85 | C9—C10 | 1.519 (5) |
O1w—H1w2 | 0.85 | C9—H9a | 0.9700 |
O2w—H2w1 | 0.85 | C9—H9b | 0.9700 |
O2w—H2w2 | 0.86 | C10—H10a | 0.9700 |
O3w—H3w1 | 0.86 | C10—H10b | 0.9700 |
O3w—H3w2 | 0.88 | C11—C12 | 1.531 (5) |
O4w—H4w1 | 0.88 | C11—H11a | 0.9700 |
O4w—H4w2 | 0.88 | C11—H11b | 0.9700 |
N1—C2 | 1.479 (4) | C13—C15 | 1.529 (5) |
N1—C20 | 1.494 (5) | C13—C14 | 1.530 (5) |
N1—C3 | 1.501 (5) | C13—H13 | 0.9800 |
N2—C9 | 1.490 (4) | C14—H14a | 0.9600 |
N2—C6 | 1.511 (5) | C14—H14b | 0.9600 |
N2—H2n | 0.8600 | C14—H14c | 0.9600 |
N3—C11 | 1.474 (4) | C15—C16 | 1.541 (5) |
N3—C10 | 1.497 (4) | C15—H15a | 0.9700 |
N3—C13 | 1.512 (4) | C15—H15b | 0.9700 |
N4—C19 | 1.487 (4) | C16—C17 | 1.526 (5) |
N4—C16 | 1.510 (5) | C16—C18 | 1.541 (5) |
N4—H4n | 0.8600 | C17—H17a | 0.9600 |
C1—C2 | 1.520 (5) | C17—H17b | 0.9600 |
C2—H2a | 0.9700 | C17—H17c | 0.9600 |
C2—H2b | 0.9700 | C18—H18a | 0.9600 |
C3—C4 | 1.531 (5) | C18—H18b | 0.9600 |
C3—C5 | 1.534 (6) | C18—H18c | 0.9600 |
C3—H3 | 0.9800 | C19—C20 | 1.524 (5) |
C4—H4a | 0.9600 | C19—H19a | 0.9700 |
C4—H4b | 0.9600 | C19—H19b | 0.9700 |
C4—H4c | 0.9600 | C20—H20a | 0.9700 |
C5—C6 | 1.535 (5) | C20—H20b | 0.9700 |
N1—Co1—N2 | 91.8 (1) | H7a—C7—H7b | 109.5 |
N1—Co1—N3 | 177.0 (1) | C6—C7—H7c | 109.5 |
N1—Co1—N4 | 85.7 (1) | H7a—C7—H7c | 109.5 |
N1—Co1—O1 | 79.2 (1) | H7b—C7—H7c | 109.5 |
N1—Co1—O3 | 103.1 (1) | C6—C8—H8a | 109.5 |
N2—Co1—N3 | 85.7 (1) | C6—C8—H8b | 109.5 |
N2—Co1—N4 | 89.9 (1) | H8a—C8—H8b | 109.5 |
N2—Co1—O1 | 169.4 (1) | C6—C8—H8c | 109.5 |
N2—Co1—O3 | 95.6 (1) | H8a—C8—H8c | 109.5 |
N3—Co1—N4 | 92.6 (1) | H8b—C8—H8c | 109.5 |
N3—Co1—O1 | 103.5 (1) | N2—C9—C10 | 111.2 (3) |
N3—Co1—O3 | 79.0 (1) | N2—C9—H9a | 109.4 |
N4—Co1—O1 | 94.8 (1) | C10—C9—H9a | 109.4 |
N4—Co1—O3 | 169.5 (1) | N2—C9—H9b | 109.4 |
O1—Co1—O3 | 81.3 (1) | C10—C9—H9b | 109.4 |
C1—O1—Co1 | 111.6 (2) | H9a—C9—H9b | 108.0 |
C12—O3—Co1 | 111.0 (2) | N3—C10—C9 | 110.9 (3) |
H1w1—O1w—H1w2 | 109.6 | N3—C10—H10a | 109.5 |
H2w1—O2w—H2w2 | 108.3 | C9—C10—H10a | 109.5 |
H3w1—O3w—H3w2 | 106.6 | N3—C10—H10b | 109.5 |
H4w1—O4w—H4w2 | 102.2 | C9—C10—H10b | 109.5 |
C2—N1—C20 | 108.8 (3) | H10a—C10—H10b | 108.1 |
C2—N1—C3 | 113.4 (3) | N3—C11—C12 | 110.1 (3) |
C20—N1—C3 | 111.7 (3) | N3—C11—H11a | 109.6 |
C2—N1—Co1 | 103.1 (2) | C12—C11—H11a | 109.6 |
C20—N1—Co1 | 105.3 (2) | N3—C11—H11b | 109.6 |
C3—N1—Co1 | 113.9 (2) | C12—C11—H11b | 109.6 |
C9—N2—C6 | 117.6 (3) | H11a—C11—H11b | 108.2 |
C9—N2—Co1 | 106.9 (2) | O3—C12—O4 | 125.5 (3) |
C6—N2—Co1 | 118.2 (2) | O3—C12—C11 | 118.4 (3) |
C9—N2—H2n | 104.1 | O4—C12—C11 | 116.2 (3) |
C6—N2—H2n | 104.1 | N3—C13—C15 | 110.3 (3) |
Co1—N2—H2n | 104.1 | N3—C13—C14 | 113.4 (3) |
C11—N3—C10 | 108.9 (3) | C15—C13—C14 | 111.4 (3) |
C11—N3—C13 | 113.6 (3) | N3—C13—H13 | 107.1 |
C10—N3—C13 | 111.5 (3) | C15—C13—H13 | 107.1 |
C11—N3—Co1 | 104.21 (19) | C14—C13—H13 | 107.1 |
C10—N3—Co1 | 105.58 (19) | C13—C14—H14a | 109.5 |
C13—N3—Co1 | 112.5 (2) | C13—C14—H14b | 109.5 |
C19—N4—C16 | 117.6 (3) | H14a—C14—H14b | 109.5 |
C19—N4—Co1 | 107.2 (2) | C13—C14—H14c | 109.5 |
C16—N4—Co1 | 117.7 (2) | H14a—C14—H14c | 109.5 |
C19—N4—H4n | 104.2 | H14b—C14—H14c | 109.5 |
C16—N4—H4n | 104.2 | C13—C15—C16 | 117.2 (3) |
Co1—N4—H4n | 104.2 | C13—C15—H15a | 108.0 |
O2—C1—O1 | 126.0 (4) | C16—C15—H15a | 108.0 |
O2—C1—C2 | 116.7 (3) | C13—C15—H15b | 108.0 |
O1—C1—C2 | 117.3 (3) | C16—C15—H15b | 108.0 |
N1—C2—C1 | 110.9 (3) | H15a—C15—H15b | 107.2 |
N1—C2—H2a | 109.5 | N4—C16—C17 | 112.3 (3) |
C1—C2—H2a | 109.5 | N4—C16—C15 | 107.8 (3) |
N1—C2—H2b | 109.5 | C17—C16—C15 | 108.3 (3) |
C1—C2—H2b | 109.5 | N4—C16—C18 | 108.1 (3) |
H2a—C2—H2b | 108.1 | C17—C16—C18 | 110.4 (3) |
N1—C3—C4 | 113.4 (3) | C15—C16—C18 | 109.8 (3) |
N1—C3—C5 | 110.1 (3) | C16—C17—H17a | 109.5 |
C4—C3—C5 | 111.4 (4) | C16—C17—H17b | 109.5 |
N1—C3—H3 | 107.2 | H17a—C17—H17b | 109.5 |
C4—C3—H3 | 107.2 | C16—C17—H17c | 109.5 |
C5—C3—H3 | 107.2 | H17a—C17—H17c | 109.5 |
C3—C4—H4a | 109.5 | H17b—C17—H17c | 109.5 |
C3—C4—H4b | 109.5 | C16—C18—H18a | 109.5 |
H4a—C4—H4b | 109.5 | C16—C18—H18b | 109.5 |
C3—C4—H4c | 109.5 | H18a—C18—H18b | 109.5 |
H4a—C4—H4c | 109.5 | C16—C18—H18c | 109.5 |
H4b—C4—H4c | 109.5 | H18a—C18—H18c | 109.5 |
C3—C5—C6 | 117.5 (4) | H18b—C18—H18c | 109.5 |
C3—C5—H5a | 107.9 | N4—C19—C20 | 111.3 (3) |
C6—C5—H5a | 107.9 | N4—C19—H19a | 109.4 |
C3—C5—H5b | 107.9 | C20—C19—H19a | 109.4 |
C6—C5—H5b | 107.9 | N4—C19—H19b | 109.4 |
H5a—C5—H5b | 107.2 | C20—C19—H19b | 109.4 |
N2—C6—C7 | 111.6 (3) | H19a—C19—H19b | 108.0 |
N2—C6—C5 | 108.2 (3) | N1—C20—C19 | 110.8 (3) |
C7—C6—C5 | 108.1 (4) | N1—C20—H20a | 109.5 |
N2—C6—C8 | 108.4 (3) | C19—C20—H20a | 109.5 |
C7—C6—C8 | 109.8 (4) | N1—C20—H20b | 109.5 |
C5—C6—C8 | 110.7 (3) | C19—C20—H20b | 109.5 |
C6—C7—H7a | 109.5 | H20a—C20—H20b | 108.1 |
C6—C7—H7b | 109.5 | ||
N3—Co1—O1—C1 | 154.5 (2) | C3—N1—C2—C1 | −164.9 (3) |
N4—Co1—O1—C1 | −111.7 (2) | Co1—N1—C2—C1 | −41.3 (3) |
N1—Co1—O1—C1 | −27.0 (2) | O2—C1—C2—N1 | −157.9 (3) |
N2—Co1—O1—C1 | 4.2 (7) | O1—C1—C2—N1 | 22.4 (5) |
O3—Co1—O1—C1 | 78.1 (2) | C2—N1—C3—C4 | −47.2 (5) |
N3—Co1—O3—C12 | −29.1 (2) | C20—N1—C3—C4 | 76.2 (4) |
N4—Co1—O3—C12 | 7.7 (7) | Co1—N1—C3—C4 | −164.7 (3) |
N1—Co1—O3—C12 | 153.2 (2) | C2—N1—C3—C5 | 78.4 (4) |
N2—Co1—O3—C12 | −113.7 (2) | C20—N1—C3—C5 | −158.3 (3) |
O1—Co1—O3—C12 | 76.5 (2) | Co1—N1—C3—C5 | −39.1 (4) |
N4—Co1—N1—C2 | 131.7 (2) | N1—C3—C5—C6 | 86.6 (4) |
N2—Co1—N1—C2 | −138.6 (2) | C4—C3—C5—C6 | −146.7 (4) |
O1—Co1—N1—C2 | 36.0 (2) | C9—N2—C6—C7 | −41.5 (4) |
O3—Co1—N1—C2 | −42.4 (2) | Co1—N2—C6—C7 | 89.2 (3) |
N4—Co1—N1—C20 | 17.7 (2) | C9—N2—C6—C5 | −160.3 (3) |
N2—Co1—N1—C20 | 107.4 (2) | Co1—N2—C6—C5 | −29.5 (4) |
O1—Co1—N1—C20 | −78.1 (2) | C9—N2—C6—C8 | 79.6 (4) |
O3—Co1—N1—C20 | −156.4 (2) | Co1—N2—C6—C8 | −149.7 (3) |
N4—Co1—N1—C3 | −105.0 (3) | C3—C5—C6—N2 | −43.3 (5) |
N2—Co1—N1—C3 | −15.2 (3) | C3—C5—C6—C7 | −164.3 (3) |
O1—Co1—N1—C3 | 159.3 (3) | C3—C5—C6—C8 | 75.4 (5) |
O3—Co1—N1—C3 | 81.0 (3) | C6—N2—C9—C10 | 103.4 (4) |
N3—Co1—N2—C9 | 7.7 (2) | Co1—N2—C9—C10 | −32.3 (3) |
N4—Co1—N2—C9 | −84.9 (2) | C11—N3—C10—C9 | −152.0 (3) |
N1—Co1—N2—C9 | −170.5 (2) | C13—N3—C10—C9 | 81.9 (3) |
O1—Co1—N2—C9 | 158.8 (5) | Co1—N3—C10—C9 | −40.6 (3) |
O3—Co1—N2—C9 | 86.2 (2) | N2—C9—C10—N3 | 50.6 (4) |
N3—Co1—N2—C6 | −127.7 (3) | C10—N3—C11—C12 | 73.6 (3) |
N4—Co1—N2—C6 | 139.8 (3) | C13—N3—C11—C12 | −161.5 (3) |
N1—Co1—N2—C6 | 54.1 (3) | Co1—N3—C11—C12 | −38.7 (3) |
O1—Co1—N2—C6 | 23.4 (7) | Co1—O3—C12—O4 | −164.2 (3) |
O3—Co1—N2—C6 | −49.2 (3) | Co1—O3—C12—C11 | 14.3 (4) |
N4—Co1—N3—C11 | −137.8 (2) | N3—C11—C12—O3 | 17.4 (4) |
N2—Co1—N3—C11 | 132.5 (2) | N3—C11—C12—O4 | −164.0 (3) |
O1—Co1—N3—C11 | −42.3 (2) | C11—N3—C13—C15 | 77.0 (3) |
O3—Co1—N3—C11 | 35.9 (2) | C10—N3—C13—C15 | −159.6 (3) |
N4—Co1—N3—C10 | 107.5 (2) | Co1—N3—C13—C15 | −41.1 (3) |
N2—Co1—N3—C10 | 17.8 (2) | C11—N3—C13—C14 | −48.8 (4) |
O1—Co1—N3—C10 | −156.96 (19) | C10—N3—C13—C14 | 74.7 (4) |
O3—Co1—N3—C10 | −78.8 (2) | Co1—N3—C13—C14 | −166.9 (3) |
N4—Co1—N3—C13 | −14.3 (2) | N3—C13—C15—C16 | 87.4 (4) |
N2—Co1—N3—C13 | −104.0 (2) | C14—C13—C15—C16 | −145.8 (3) |
O1—Co1—N3—C13 | 81.2 (2) | C19—N4—C16—C17 | −42.7 (4) |
O3—Co1—N3—C13 | 159.4 (2) | Co1—N4—C16—C17 | 87.9 (3) |
N3—Co1—N4—C19 | −169.5 (2) | C19—N4—C16—C15 | −162.0 (3) |
N1—Co1—N4—C19 | 8.0 (2) | Co1—N4—C16—C15 | −31.3 (4) |
N2—Co1—N4—C19 | −83.8 (2) | C19—N4—C16—C18 | 79.3 (4) |
O1—Co1—N4—C19 | 86.7 (2) | Co1—N4—C16—C18 | −150.1 (3) |
O3—Co1—N4—C19 | 154.4 (5) | C13—C15—C16—N4 | −41.4 (4) |
N3—Co1—N4—C16 | 55.2 (2) | C13—C15—C16—C17 | −163.2 (3) |
N1—Co1—N4—C16 | −127.3 (2) | C13—C15—C16—C18 | 76.2 (4) |
N2—Co1—N4—C16 | 140.9 (2) | C16—N4—C19—C20 | 102.7 (4) |
O1—Co1—N4—C16 | −48.5 (2) | Co1—N4—C19—C20 | −32.6 (4) |
O3—Co1—N4—C16 | 19.1 (7) | C2—N1—C20—C19 | −150.4 (3) |
Co1—O1—C1—O2 | −169.5 (3) | C3—N1—C20—C19 | 83.7 (4) |
Co1—O1—C1—C2 | 10.1 (4) | Co1—N1—C20—C19 | −40.4 (3) |
C20—N1—C2—C1 | 70.2 (4) | N4—C19—C20—N1 | 50.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2n···O4i | 0.86 | 2.44 | 3.164 (4) | 143 |
N4—H4n···O4i | 0.86 | 2.22 | 2.993 (4) | 150 |
O1w—H1w1···O1 | 0.85 | 2.06 | 2.901 (4) | 169 |
O1w—H1w2···O4w | 0.85 | 2.30 | 2.95 (1) | 133 |
O2w—H2w1···O1w | 0.85 | 2.00 | 2.827 (8) | 164 |
O2w—H2w2···O3wii | 0.86 | 1.87 | 2.57 (1) | 138 |
O3w—H3w1···O4iii | 0.86 | 2.17 | 2.817 (7) | 132 |
O3w—H3w2···O4w | 0.88 | 1.75 | 2.40 (1) | 128 |
O4w—H4w2···O2 | 0.88 | 2.06 | 2.704 (9) | 129 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z. |