metal-organic compounds
The two Mn atoms in the crystal structure of the title compound, [Mn2(C8H4O5)2(C10H8N2)2]n, are each chelated by the bipyridine heterocycle as well as by the carboxyl group of the dianionic ligand. Each Mn atom is covalently linked to the singly bonded carboxylate O atom of a second dianion and is datively linked to the carbonyl O atom of a third dianion. The Mn atoms exist in octahedral geometries in the linear polymeric chain.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027685/ci6313sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027685/ci6313Isup2.hkl |
CCDC reference: 231816
Computing details top
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); 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.
Crystal data top
[Mn2(C10H8N2)2(C8H4O5)2] | Z = 2 |
Mr = 782.47 | F(000) = 796 |
Triclinic, P1 | Dx = 1.610 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.473 (1) Å | Cell parameters from 883 reflections |
b = 10.694 (1) Å | θ = 2.6–26.6° |
c = 17.900 (2) Å | µ = 0.85 mm−1 |
α = 79.413 (2)° | T = 298 K |
β = 86.879 (3)° | Prism, pale yellow |
γ = 64.923 (2)° | 0.50 × 0.24 × 0.14 mm |
V = 1613.9 (3) Å3 |
Data collection top
Bruker AXS 1K area-detector diffractometer | 5605 independent reflections |
Radiation source: normal-focus sealed tube | 4418 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→10 |
Tmin = 0.789, Tmax = 0.890 | k = −12→12 |
8340 measured reflections | l = −12→21 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0654P)2 + 0.961P] where P = (Fo2 + 2Fc2)/3 |
5605 reflections | (Δ/σ)max < 0.001 |
471 parameters | Δρmax = 1.23 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.36821 (6) | 0.37240 (5) | 0.52095 (2) | 0.0372 (2) | |
Mn2 | 0.54958 (6) | −0.11682 (5) | 0.90345 (2) | 0.0372 (2) | |
O1 | 0.3370 (3) | 0.2618 (3) | 0.6424 (1) | 0.053 (1) | |
O2 | 0.1801 (3) | 0.4814 (3) | 0.6017 (1) | 0.056 (1) | |
O3 | −0.0056 (3) | 0.6301 (3) | 0.6926 (2) | 0.074 (1) | |
O4 | 0.3198 (3) | 0.2379 (3) | 0.9976 (1) | 0.054 (1) | |
O5 | 0.4183 (4) | 0.0850 (2) | 0.9218 (1) | 0.069 (1) | |
O6 | 0.5839 (3) | −0.0082 (2) | 0.7826 (2) | 0.053 (1) | |
O7 | 0.7828 (3) | −0.1035 (3) | 0.8634 (1) | 0.059 (1) | |
O8 | 1.0181 (3) | −0.0451 (3) | 0.8401 (2) | 0.068 (1) | |
O9 | 0.7434 (3) | 0.4492 (2) | 0.5622 (1) | 0.053 (1) | |
O10 | 0.5523 (3) | 0.3821 (3) | 0.5749 (1) | 0.060 (1) | |
N1 | 0.2682 (3) | 0.2413 (3) | 0.4797 (1) | 0.042 (1) | |
N2 | 0.5362 (3) | 0.2519 (3) | 0.4379 (2) | 0.041 (1) | |
N3 | 0.3565 (3) | −0.1809 (3) | 0.9495 (2) | 0.046 (1) | |
N4 | 0.5593 (3) | −0.2896 (3) | 0.8454 (1) | 0.038 (1) | |
C1 | 0.2405 (4) | 0.3768 (4) | 0.6549 (2) | 0.042 (1) | |
C2 | 0.1942 (3) | 0.3983 (3) | 0.7345 (2) | 0.036 (1) | |
C3 | 0.0785 (4) | 0.5246 (3) | 0.7490 (2) | 0.041 (1) | |
C4 | 0.0439 (4) | 0.5446 (3) | 0.8236 (2) | 0.046 (1) | |
C5 | 0.1239 (3) | 0.4400 (3) | 0.8826 (2) | 0.039 (1) | |
C6 | 0.2405 (3) | 0.3126 (3) | 0.8695 (2) | 0.034 (1) | |
C7 | 0.2735 (3) | 0.2933 (3) | 0.7952 (2) | 0.034 (1) | |
C8 | 0.3325 (4) | 0.2032 (3) | 0.9336 (2) | 0.038 (1) | |
C9 | 0.7134 (4) | −0.0193 (3) | 0.8038 (2) | 0.043 (1) | |
C10 | 0.7865 (3) | 0.0690 (3) | 0.7606 (2) | 0.035 (1) | |
C11 | 0.9323 (4) | 0.0558 (3) | 0.7826 (2) | 0.041 (1) | |
C12 | 0.9920 (4) | 0.1476 (3) | 0.7455 (2) | 0.046 (1) | |
C13 | 0.9121 (4) | 0.2482 (3) | 0.6848 (2) | 0.040 (1) | |
C14 | 0.7691 (3) | 0.2608 (3) | 0.6598 (2) | 0.032 (1) | |
C15 | 0.7065 (3) | 0.1724 (3) | 0.6994 (2) | 0.032 (1) | |
C16 | 0.6817 (4) | 0.3711 (3) | 0.5944 (2) | 0.038 (1) | |
C17 | 0.1316 (4) | 0.2416 (4) | 0.5022 (2) | 0.054 (1) | |
C18 | 0.0781 (5) | 0.1514 (5) | 0.4822 (2) | 0.065 (1) | |
C19 | 0.1671 (5) | 0.0592 (5) | 0.4369 (3) | 0.070 (1) | |
C20 | 0.3057 (5) | 0.0581 (4) | 0.4127 (2) | 0.058 (1) | |
C21 | 0.3549 (4) | 0.1517 (3) | 0.4343 (2) | 0.038 (1) | |
C22 | 0.4993 (4) | 0.1634 (3) | 0.4073 (2) | 0.040 (1) | |
C23 | 0.5864 (4) | 0.0963 (4) | 0.3513 (2) | 0.060 (1) | |
C24 | 0.7106 (5) | 0.1235 (5) | 0.3242 (3) | 0.076 (1) | |
C25 | 0.7480 (5) | 0.2135 (5) | 0.3546 (3) | 0.067 (1) | |
C26 | 0.6586 (4) | 0.2747 (4) | 0.4116 (2) | 0.053 (1) | |
C27 | 0.2587 (5) | −0.1244 (4) | 1.0029 (2) | 0.063 (1) | |
C28 | 0.1677 (6) | −0.1837 (6) | 1.0414 (3) | 0.090 (2) | |
C29 | 0.1823 (7) | −0.3108 (7) | 1.0273 (3) | 0.102 (2) | |
C30 | 0.2812 (6) | −0.3695 (5) | 0.9725 (3) | 0.081 (1) | |
C31 | 0.3638 (4) | −0.3014 (4) | 0.9334 (2) | 0.050 (1) | |
C32 | 0.4671 (4) | −0.3539 (4) | 0.8705 (2) | 0.047 (1) | |
C33 | 0.4661 (6) | −0.4594 (5) | 0.8370 (3) | 0.081 (2) | |
C34 | 0.5619 (6) | −0.5015 (5) | 0.7783 (3) | 0.094 (2) | |
C35 | 0.6573 (5) | −0.4370 (4) | 0.7524 (3) | 0.068 (1) | |
C36 | 0.6514 (4) | −0.3311 (3) | 0.7874 (2) | 0.047 (1) | |
H3 | 0.0317 | 0.6115 | 0.6515 | 0.089* | |
H8 | 0.9685 | −0.0890 | 0.8597 | 0.101* | |
H4 | −0.0335 | 0.6289 | 0.8334 | 0.055* | |
H5 | 0.1001 | 0.4542 | 0.9324 | 0.046* | |
H7 | 0.3501 | 0.2085 | 0.7856 | 0.041* | |
H12 | 1.0869 | 0.1410 | 0.7618 | 0.056* | |
H13 | 0.9538 | 0.3088 | 0.6600 | 0.048* | |
H15 | 0.6090 | 0.1826 | 0.6846 | 0.039* | |
H17 | 0.0704 | 0.3055 | 0.5326 | 0.065* | |
H18 | −0.0170 | 0.1530 | 0.4993 | 0.078* | |
H19 | 0.1329 | −0.0028 | 0.4226 | 0.084* | |
H20 | 0.3672 | −0.0049 | 0.3820 | 0.069* | |
H23 | 0.5617 | 0.0330 | 0.3318 | 0.071* | |
H24 | 0.7691 | 0.0806 | 0.2852 | 0.091* | |
H25 | 0.8322 | 0.2328 | 0.3372 | 0.080* | |
H26 | 0.6847 | 0.3353 | 0.4330 | 0.063* | |
H27 | 0.2524 | −0.0408 | 1.0144 | 0.076* | |
H28 | 0.0971 | −0.1390 | 1.0765 | 0.107* | |
H29 | 0.1256 | −0.3559 | 1.0546 | 0.123* | |
H30 | 0.2924 | −0.4551 | 0.9619 | 0.097* | |
H33 | 0.4001 | −0.5020 | 0.8544 | 0.097* | |
H34 | 0.5624 | −0.5736 | 0.7559 | 0.113* | |
H35 | 0.7239 | −0.4641 | 0.7125 | 0.082* | |
H36 | 0.7149 | −0.2859 | 0.7697 | 0.056* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0552 (3) | 0.0384 (3) | 0.0253 (2) | −0.0268 (2) | 0.0023 (2) | −0.0058 (2) |
Mn2 | 0.0542 (3) | 0.0365 (3) | 0.0258 (2) | −0.0242 (2) | −0.0033 (2) | −0.0034 (2) |
O1 | 0.060 (2) | 0.064 (2) | 0.033 (1) | −0.022 (1) | 0.003 (1) | −0.016 (1) |
O2 | 0.069 (2) | 0.064 (2) | 0.026 (1) | −0.024 (1) | −0.002 (1) | 0.005 (1) |
O3 | 0.074 (2) | 0.069 (2) | 0.053 (2) | −0.013 (2) | −0.005 (1) | 0.009 (1) |
O4 | 0.065 (2) | 0.064 (2) | 0.025 (1) | −0.019 (1) | −0.005 (1) | −0.004 (1) |
O5 | 0.105 (2) | 0.035 (1) | 0.045 (1) | −0.009 (1) | −0.013 (1) | 0.001 (1) |
O6 | 0.055 (2) | 0.043 (1) | 0.063 (2) | −0.028 (1) | 0.006 (1) | −0.001 (1) |
O7 | 0.078 (2) | 0.051 (1) | 0.043 (1) | −0.031 (1) | −0.003 (1) | 0.011 (1) |
O8 | 0.065 (2) | 0.061 (2) | 0.063 (2) | −0.020 (1) | −0.018 (1) | 0.010 (1) |
O9 | 0.068 (2) | 0.048 (1) | 0.039 (1) | −0.029 (1) | 0.005 (1) | 0.006 (1) |
O10 | 0.079 (2) | 0.065 (2) | 0.044 (1) | −0.041 (1) | −0.023 (1) | 0.007 (1) |
N1 | 0.056 (2) | 0.049 (2) | 0.032 (1) | −0.032 (1) | 0.003 (1) | −0.007 (1) |
N2 | 0.047 (2) | 0.042 (1) | 0.039 (1) | −0.023 (1) | 0.001 (1) | −0.010 (1) |
N3 | 0.053 (2) | 0.052 (2) | 0.040 (2) | −0.025 (1) | 0.005 (1) | −0.018 (1) |
N4 | 0.044 (1) | 0.037 (1) | 0.036 (1) | −0.019 (1) | 0.002 (1) | −0.009 (1) |
C1 | 0.047 (2) | 0.060 (2) | 0.025 (2) | −0.028 (2) | −0.003 (1) | −0.004 (2) |
C2 | 0.040 (2) | 0.044 (2) | 0.026 (2) | −0.021 (1) | 0.000 (1) | −0.004 (1) |
C3 | 0.038 (2) | 0.044 (2) | 0.033 (2) | −0.015 (1) | −0.004 (1) | 0.005 (1) |
C4 | 0.041 (2) | 0.044 (2) | 0.044 (2) | −0.010 (2) | 0.001 (2) | −0.009 (2) |
C5 | 0.043 (2) | 0.050 (2) | 0.026 (2) | −0.022 (2) | 0.005 (1) | −0.009 (1) |
C6 | 0.043 (2) | 0.037 (2) | 0.026 (1) | −0.022 (1) | −0.001 (1) | −0.003 (1) |
C7 | 0.043 (2) | 0.035 (2) | 0.026 (1) | −0.019 (1) | 0.000 (1) | −0.004 (1) |
C8 | 0.048 (2) | 0.041 (2) | 0.028 (2) | −0.024 (2) | −0.001 (1) | −0.001 (1) |
C9 | 0.058 (2) | 0.031 (2) | 0.040 (2) | −0.018 (2) | 0.009 (2) | −0.008 (1) |
C10 | 0.045 (2) | 0.030 (2) | 0.033 (2) | −0.016 (1) | 0.006 (1) | −0.009 (1) |
C11 | 0.046 (2) | 0.036 (2) | 0.034 (2) | −0.011 (1) | −0.001 (1) | −0.005 (1) |
C12 | 0.039 (2) | 0.049 (2) | 0.051 (2) | −0.019 (2) | −0.002 (2) | −0.010 (2) |
C13 | 0.043 (2) | 0.039 (2) | 0.041 (2) | −0.021 (1) | 0.010 (1) | −0.010 (1) |
C14 | 0.047 (2) | 0.028 (1) | 0.026 (1) | −0.018 (1) | 0.005 (1) | −0.009 (1) |
C15 | 0.038 (2) | 0.032 (2) | 0.028 (1) | −0.014 (1) | 0.000 (1) | −0.009 (1) |
C16 | 0.054 (2) | 0.036 (2) | 0.024 (1) | −0.020 (2) | 0.005 (1) | −0.009 (1) |
C17 | 0.063 (2) | 0.071 (2) | 0.044 (2) | −0.042 (2) | 0.011 (2) | −0.014 (2) |
C18 | 0.075 (3) | 0.087 (3) | 0.058 (2) | −0.059 (2) | 0.008 (2) | −0.012 (2) |
C19 | 0.090 (3) | 0.077 (3) | 0.076 (3) | −0.063 (3) | 0.005 (2) | −0.024 (2) |
C20 | 0.071 (2) | 0.053 (2) | 0.064 (2) | −0.037 (2) | 0.000 (2) | −0.020 (2) |
C21 | 0.053 (2) | 0.032 (2) | 0.031 (2) | −0.019 (1) | −0.007 (1) | −0.004 (1) |
C22 | 0.047 (2) | 0.034 (2) | 0.039 (2) | −0.015 (1) | −0.005 (1) | −0.008 (1) |
C23 | 0.057 (2) | 0.061 (2) | 0.068 (2) | −0.023 (2) | 0.010 (2) | −0.038 (2) |
C24 | 0.057 (2) | 0.088 (3) | 0.088 (3) | −0.024 (2) | 0.026 (2) | −0.050 (3) |
C25 | 0.050 (2) | 0.077 (3) | 0.080 (3) | −0.029 (2) | 0.019 (2) | −0.029 (2) |
C26 | 0.051 (2) | 0.057 (2) | 0.060 (2) | −0.030 (2) | 0.007 (2) | −0.017 (2) |
C27 | 0.076 (3) | 0.072 (3) | 0.055 (2) | −0.038 (2) | 0.024 (2) | −0.035 (2) |
C28 | 0.101 (4) | 0.133 (4) | 0.071 (3) | −0.073 (4) | 0.049 (3) | −0.057 (3) |
C29 | 0.128 (4) | 0.143 (5) | 0.094 (4) | −0.105 (4) | 0.062 (3) | −0.058 (4) |
C30 | 0.108 (4) | 0.098 (3) | 0.082 (3) | −0.078 (3) | 0.042 (3) | −0.045 (3) |
C31 | 0.060 (2) | 0.058 (2) | 0.046 (2) | −0.036 (2) | 0.010 (2) | −0.020 (2) |
C32 | 0.057 (2) | 0.045 (2) | 0.051 (2) | −0.029 (2) | 0.011 (2) | −0.020 (2) |
C33 | 0.100 (3) | 0.079 (3) | 0.104 (4) | −0.066 (3) | 0.049 (3) | −0.056 (3) |
C34 | 0.113 (4) | 0.090 (3) | 0.120 (4) | −0.065 (3) | 0.059 (3) | −0.078 (3) |
C35 | 0.069 (3) | 0.067 (3) | 0.077 (3) | −0.029 (2) | 0.029 (2) | −0.041 (2) |
C36 | 0.048 (2) | 0.048 (2) | 0.047 (2) | −0.021 (2) | 0.008 (2) | −0.016 (2) |
Geometric parameters (Å, º) top
Mn1—O1 | 2.344 (2) | C14—C15 | 1.389 (4) |
Mn1—O2 | 2.280 (2) | C14—C16 | 1.490 (4) |
Mn1—O9i | 2.096 (2) | C17—C18 | 1.371 (5) |
Mn1—O10 | 2.088 (2) | C18—C19 | 1.362 (6) |
Mn1—N1 | 2.235 (3) | C19—C20 | 1.356 (6) |
Mn1—N2 | 2.261 (3) | C20—C21 | 1.388 (4) |
Mn2—O4ii | 2.093 (2) | C21—C22 | 1.472 (5) |
Mn2—O5 | 2.062 (3) | C22—C23 | 1.370 (5) |
Mn2—O6 | 2.336 (2) | C23—C24 | 1.371 (6) |
Mn2—O7 | 2.339 (3) | C24—C25 | 1.361 (6) |
Mn2—N3 | 2.277 (3) | C25—C26 | 1.366 (5) |
Mn2—N4 | 2.248 (2) | C27—C28 | 1.363 (6) |
O1—C1 | 1.234 (4) | C28—C29 | 1.376 (7) |
O2—C1 | 1.270 (4) | C29—C30 | 1.364 (6) |
O3—C3 | 1.354 (4) | C30—C31 | 1.368 (5) |
O4—C8 | 1.253 (4) | C31—C32 | 1.479 (5) |
O5—C8 | 1.230 (4) | C32—C33 | 1.376 (5) |
O6—C9 | 1.255 (4) | C33—C34 | 1.361 (6) |
O7—C9 | 1.267 (4) | C34—C35 | 1.368 (6) |
O8—C11 | 1.351 (4) | C35—C36 | 1.372 (5) |
O9—C16 | 1.253 (4) | O3—H3 | 0.82 |
O10—C16 | 1.244 (4) | O8—H8 | 0.82 |
N1—C17 | 1.332 (4) | C4—H4 | 0.93 |
N1—C21 | 1.341 (4) | C5—H5 | 0.93 |
N2—C26 | 1.328 (4) | C7—H7 | 0.93 |
N2—C22 | 1.345 (4) | C12—H12 | 0.93 |
N3—C27 | 1.334 (4) | C13—H13 | 0.93 |
N3—C31 | 1.343 (4) | C15—H15 | 0.93 |
N4—C36 | 1.334 (4) | C17—H17 | 0.93 |
N4—C32 | 1.339 (4) | C18—H18 | 0.93 |
C1—C2 | 1.497 (4) | C19—H19 | 0.93 |
C2—C3 | 1.391 (4) | C20—H20 | 0.93 |
C2—C7 | 1.389 (4) | C23—H23 | 0.93 |
C3—C4 | 1.391 (5) | C24—H24 | 0.93 |
C4—C5 | 1.370 (4) | C25—H25 | 0.93 |
C5—C6 | 1.395 (4) | C26—H26 | 0.93 |
C6—C7 | 1.382 (4) | C27—H27 | 0.93 |
C6—C8 | 1.482 (4) | C28—H28 | 0.93 |
C9—C10 | 1.482 (4) | C29—H29 | 0.93 |
C10—C15 | 1.389 (4) | C30—H30 | 0.93 |
C10—C11 | 1.399 (4) | C33—H33 | 0.93 |
C11—C12 | 1.383 (4) | C34—H34 | 0.93 |
C12—C13 | 1.372 (5) | C35—H35 | 0.93 |
C13—C14 | 1.394 (4) | C36—H36 | 0.93 |
O1—Mn1—O2 | 56.5 (1) | C15—C14—C16 | 120.7 (3) |
O1—Mn1—O9i | 142.7 (1) | C13—C14—C16 | 120.7 (3) |
O1—Mn1—O10 | 83.0 (1) | C14—C15—C10 | 121.3 (3) |
O1—Mn1—N1 | 84.7 (1) | O10—C16—O9 | 123.5 (3) |
O1—Mn1—N2 | 121.8 (1) | O10—C16—C14 | 119.1 (3) |
O2—Mn1—O9i | 87.1 (1) | O9—C16—C14 | 117.4 (3) |
O2—Mn1—O10 | 96.4 (1) | N1—C17—C18 | 122.4 (4) |
O2—Mn1—N1 | 100.8 (1) | C19—C18—C17 | 118.7 (4) |
O2—Mn1—N2 | 173.1 (1) | C20—C19—C18 | 119.9 (4) |
O9i—Mn1—O10 | 111.5 (1) | C19—C20—C21 | 119.4 (4) |
O9i—Mn1—N1 | 95.8 (1) | N1—C21—C20 | 120.7 (3) |
O9i—Mn1—N2 | 93.3 (1) | N1—C21—C22 | 116.1 (3) |
O10—Mn1—N1 | 148.4 (1) | C20—C21—C22 | 123.2 (3) |
O10—Mn1—N2 | 89.9 (1) | N2—C22—C23 | 121.2 (3) |
N1—Mn1—N2 | 72.3 (1) | N2—C22—C21 | 115.8 (3) |
O4ii—Mn2—O5 | 109.1 (1) | C23—C22—C21 | 122.9 (3) |
O4ii—Mn2—O6 | 139.6 (1) | C22—C23—C24 | 119.2 (4) |
O4ii—Mn2—O7 | 83.9 (1) | C25—C24—C23 | 119.7 (4) |
O4ii—Mn2—N3 | 87.7 (1) | C24—C25—C26 | 118.2 (4) |
O4ii—Mn2—N4 | 99.4 (1) | N2—C26—C25 | 123.2 (3) |
O5—Mn2—O6 | 84.7 (1) | N3—C27—C28 | 122.9 (4) |
O5—Mn2—O7 | 101.0 (1) | C27—C28—C29 | 118.8 (4) |
O5—Mn2—N3 | 90.6 (1) | C30—C29—C28 | 118.9 (4) |
O5—Mn2—N4 | 145.9 (1) | C29—C30—C31 | 119.4 (4) |
O6—Mn2—O7 | 56.0 (1) | N3—C31—C30 | 122.1 (3) |
O6—Mn2—N3 | 131.0 (1) | N3—C31—C32 | 115.0 (3) |
O6—Mn2—N4 | 85.6 (1) | C30—C31—C32 | 122.8 (3) |
O7—Mn2—N3 | 167.4 (1) | N4—C32—C33 | 120.9 (3) |
O7—Mn2—N4 | 100.4 (1) | N4—C32—C31 | 116.3 (3) |
N3—Mn2—N4 | 71.7 (1) | C33—C32—C31 | 122.7 (3) |
C1—O1—Mn1 | 88.8 (2) | C34—C33—C32 | 120.0 (4) |
C1—O2—Mn1 | 90.8 (2) | C33—C34—C35 | 119.6 (4) |
C8—O4—Mn2ii | 126.9 (2) | C34—C35—C36 | 117.8 (4) |
C8—O5—Mn2 | 176.1 (3) | N4—C36—C35 | 123.4 (3) |
C9—O6—Mn2 | 90.4 (2) | C3—O3—H3 | 109.5 |
C9—O7—Mn2 | 89.9 (2) | C11—O8—H8 | 109.5 |
C16—O9—Mn1i | 124.5 (2) | C5—C4—H4 | 120.0 |
C16—O10—Mn1 | 165.3 (2) | C3—C4—H4 | 120.0 |
C17—N1—C21 | 119.0 (3) | C4—C5—H5 | 119.4 |
C17—N1—Mn1 | 122.9 (2) | C6—C5—H5 | 119.4 |
C21—N1—Mn1 | 118.0 (2) | C6—C7—H7 | 119.4 |
C26—N2—C22 | 118.4 (3) | C2—C7—H7 | 119.4 |
C26—N2—Mn1 | 123.8 (2) | C13—C12—H12 | 119.8 |
C22—N2—Mn1 | 117.3 (2) | C11—C12—H12 | 119.8 |
C27—N3—C31 | 117.7 (3) | C12—C13—H13 | 119.6 |
C27—N3—Mn2 | 124.1 (2) | C14—C13—H13 | 119.6 |
C31—N3—Mn2 | 116.7 (2) | C14—C15—H15 | 119.3 |
C36—N4—C32 | 118.3 (3) | C10—C15—H15 | 119.3 |
C36—N4—Mn2 | 123.7 (2) | N1—C17—H17 | 118.8 |
C32—N4—Mn2 | 118.0 (2) | C18—C17—H17 | 118.8 |
O1—C1—O2 | 121.7 (3) | C19—C18—H18 | 120.7 |
O1—C1—C2 | 120.6 (3) | C17—C18—H18 | 120.7 |
O2—C1—C2 | 117.6 (3) | C20—C19—H19 | 120.1 |
C3—C2—C7 | 119.3 (3) | C18—C19—H19 | 120.1 |
C3—C2—C1 | 121.1 (3) | C19—C20—H20 | 120.3 |
C7—C2—C1 | 119.5 (3) | C21—C20—H20 | 120.3 |
O3—C3—C2 | 122.3 (3) | C22—C23—H23 | 120.4 |
O3—C3—C4 | 117.7 (3) | C24—C23—H23 | 120.4 |
C2—C3—C4 | 119.9 (3) | C25—C24—H24 | 120.1 |
C5—C4—C3 | 119.9 (3) | C23—C24—H24 | 120.1 |
C4—C5—C6 | 121.2 (3) | C24—C25—H25 | 120.9 |
C7—C6—C5 | 118.5 (3) | C26—C25—H25 | 120.9 |
C7—C6—C8 | 120.7 (3) | N2—C26—H26 | 118.4 |
C5—C6—C8 | 120.7 (3) | C25—C26—H26 | 118.4 |
C6—C7—C2 | 121.2 (3) | N3—C27—H27 | 118.6 |
O5—C8—O4 | 123.3 (3) | C28—C27—H27 | 118.6 |
O5—C8—C6 | 119.4 (3) | C27—C28—H28 | 120.6 |
O4—C8—C6 | 117.3 (3) | C29—C28—H28 | 120.6 |
O6—C9—O7 | 120.8 (3) | C30—C29—H29 | 120.6 |
O6—C9—C10 | 120.6 (3) | C28—C29—H29 | 120.6 |
O7—C9—C10 | 118.5 (3) | C29—C30—H30 | 120.3 |
C15—C10—C11 | 118.7 (3) | C31—C30—H30 | 120.3 |
C15—C10—C9 | 120.0 (3) | C34—C33—H33 | 120.0 |
C11—C10—C9 | 121.2 (3) | C32—C33—H33 | 120.0 |
O8—C11—C12 | 118.2 (3) | C33—C34—H34 | 120.2 |
O8—C11—C10 | 121.6 (3) | C35—C34—H34 | 120.2 |
C12—C11—C10 | 120.2 (3) | C34—C35—H35 | 121.1 |
C13—C12—C11 | 120.3 (3) | C36—C35—H35 | 121.1 |
C12—C13—C14 | 120.8 (3) | N4—C36—H36 | 118.3 |
C15—C14—C13 | 118.6 (3) | C35—C36—H36 | 118.3 |
O10—Mn1—O1—C1 | 94.0 (2) | C7—C6—C8—O5 | −13.6 (4) |
O9i—Mn1—O1—C1 | −22.6 (3) | C5—C6—C8—O5 | 169.5 (3) |
N1—Mn1—O1—C1 | −115.2 (2) | C7—C6—C8—O4 | 165.3 (3) |
N2—Mn1—O1—C1 | 179.5 (2) | C5—C6—C8—O4 | −11.6 (4) |
O2—Mn1—O1—C1 | −8.5 (2) | Mn2—O6—C9—O7 | 17.2 (3) |
O10—Mn1—O2—C1 | −69.0 (2) | Mn2—O6—C9—C10 | −161.1 (3) |
O9i—Mn1—O2—C1 | 179.7 (2) | Mn2—O7—C9—O6 | −17.2 (3) |
N1—Mn1—O2—C1 | 84.4 (2) | Mn2—O7—C9—C10 | 161.1 (2) |
O1—Mn1—O2—C1 | 8.2 (2) | O6—C9—C10—C15 | 4.9 (4) |
O5—Mn2—O6—C9 | 97.5 (2) | O7—C9—C10—C15 | −173.5 (3) |
O4ii—Mn2—O6—C9 | −16.1 (3) | O6—C9—C10—C11 | −178.7 (3) |
N4—Mn2—O6—C9 | −115.3 (2) | O7—C9—C10—C11 | 3.0 (4) |
N3—Mn2—O6—C9 | −176.3 (2) | C15—C10—C11—O8 | −178.0 (3) |
O7—Mn2—O6—C9 | −9.6 (2) | C9—C10—C11—O8 | 5.5 (5) |
O5—Mn2—O7—C9 | −66.4 (2) | C15—C10—C11—C12 | 2.2 (4) |
O4ii—Mn2—O7—C9 | −174.7 (2) | C9—C10—C11—C12 | −174.3 (3) |
N4—Mn2—O7—C9 | 86.8 (2) | O8—C11—C12—C13 | 177.3 (3) |
N3—Mn2—O7—C9 | 136.9 (4) | C10—C11—C12—C13 | −2.9 (5) |
O6—Mn2—O7—C9 | 9.5 (2) | C11—C12—C13—C14 | 0.6 (5) |
O9i—Mn1—O10—C16 | −93.2 (9) | C12—C13—C14—C15 | 2.2 (4) |
N1—Mn1—O10—C16 | 54.6 (9) | C12—C13—C14—C16 | 179.3 (3) |
N2—Mn1—O10—C16 | 0.4 (9) | C13—C14—C15—C10 | −2.8 (4) |
O2—Mn1—O10—C16 | 177.4 (9) | C16—C14—C15—C10 | −180.0 (3) |
O1—Mn1—O10—C16 | 122.5 (9) | C11—C10—C15—C14 | 0.6 (4) |
O10—Mn1—N1—C17 | 122.3 (3) | C9—C10—C15—C14 | 177.2 (3) |
O9i—Mn1—N1—C17 | −87.5 (3) | Mn1—O10—C16—O9 | 80.4 (9) |
N2—Mn1—N1—C17 | −179.2 (3) | Mn1—O10—C16—C14 | −100.3 (9) |
O2—Mn1—N1—C17 | 0.6 (3) | Mn1i—O9—C16—O10 | 7.9 (4) |
O1—Mn1—N1—C17 | 54.9 (3) | Mn1i—O9—C16—C14 | −171.5 (2) |
O10—Mn1—N1—C21 | −53.1 (3) | C15—C14—C16—O10 | −0.8 (4) |
O9i—Mn1—N1—C21 | 97.0 (2) | C13—C14—C16—O10 | −177.9 (3) |
N2—Mn1—N1—C21 | 5.4 (2) | C15—C14—C16—O9 | 178.5 (3) |
O2—Mn1—N1—C21 | −174.8 (2) | C13—C14—C16—O9 | 1.5 (4) |
O1—Mn1—N1—C21 | −120.5 (2) | C21—N1—C17—C18 | 1.7 (5) |
O10—Mn1—N2—C26 | −35.6 (3) | Mn1—N1—C17—C18 | −173.7 (3) |
O9i—Mn1—N2—C26 | 75.9 (3) | N1—C17—C18—C19 | −0.8 (6) |
N1—Mn1—N2—C26 | 170.9 (3) | C17—C18—C19—C20 | 0.2 (7) |
O1—Mn1—N2—C26 | −117.3 (3) | C18—C19—C20—C21 | −0.3 (6) |
O10—Mn1—N2—C22 | 152.0 (2) | C17—N1—C21—C20 | −1.8 (5) |
O9i—Mn1—N2—C22 | −96.4 (2) | Mn1—N1—C21—C20 | 173.8 (2) |
N1—Mn1—N2—C22 | −1.5 (2) | C17—N1—C21—C22 | 176.0 (3) |
O1—Mn1—N2—C22 | 70.3 (2) | Mn1—N1—C21—C22 | −8.4 (3) |
O5—Mn2—N3—C27 | −30.9 (3) | C19—C20—C21—N1 | 1.2 (5) |
O4ii—Mn2—N3—C27 | 78.2 (3) | C19—C20—C21—C22 | −176.5 (3) |
N4—Mn2—N3—C27 | 178.9 (3) | C26—N2—C22—C23 | 1.0 (5) |
O6—Mn2—N3—C27 | −114.4 (3) | Mn1—N2—C22—C23 | 173.8 (3) |
O7—Mn2—N3—C27 | 126.2 (5) | C26—N2—C22—C21 | −175.0 (3) |
O5—Mn2—N3—C31 | 163.6 (3) | Mn1—N2—C22—C21 | −2.2 (3) |
O4ii—Mn2—N3—C31 | −87.3 (3) | N1—C21—C22—N2 | 6.9 (4) |
N4—Mn2—N3—C31 | 13.3 (2) | C20—C21—C22—N2 | −175.3 (3) |
O6—Mn2—N3—C31 | 80.0 (3) | N1—C21—C22—C23 | −169.0 (3) |
O7—Mn2—N3—C31 | −39.3 (6) | C20—C21—C22—C23 | 8.8 (5) |
O5—Mn2—N4—C36 | 110.1 (3) | N2—C22—C23—C24 | −2.1 (6) |
O4ii—Mn2—N4—C36 | −103.3 (3) | C21—C22—C23—C24 | 173.6 (4) |
N3—Mn2—N4—C36 | 172.2 (3) | C22—C23—C24—C25 | 1.8 (7) |
O6—Mn2—N4—C36 | 36.3 (2) | C23—C24—C25—C26 | −0.3 (7) |
O7—Mn2—N4—C36 | −17.9 (3) | C22—N2—C26—C25 | 0.5 (5) |
O5—Mn2—N4—C32 | −69.7 (3) | Mn1—N2—C26—C25 | −171.8 (3) |
O4ii—Mn2—N4—C32 | 76.9 (2) | C24—C25—C26—N2 | −0.8 (6) |
N3—Mn2—N4—C32 | −7.5 (2) | C31—N3—C27—C28 | 0.2 (6) |
O6—Mn2—N4—C32 | −143.5 (2) | Mn2—N3—C27—C28 | −165.2 (4) |
O7—Mn2—N4—C32 | 162.3 (2) | N3—C27—C28—C29 | 3.2 (8) |
Mn1—O1—C1—O2 | 15.0 (3) | C27—C28—C29—C30 | −3.4 (9) |
Mn1—O1—C1—C2 | −163.2 (3) | C28—C29—C30—C31 | 0.3 (9) |
Mn1—O2—C1—O1 | −15.4 (3) | C27—N3—C31—C30 | −3.5 (6) |
Mn1—O2—C1—C2 | 162.8 (2) | Mn2—N3—C31—C30 | 163.0 (4) |
O1—C1—C2—C3 | −175.9 (3) | C27—N3—C31—C32 | 176.4 (3) |
O2—C1—C2—C3 | 5.9 (4) | Mn2—N3—C31—C32 | −17.1 (4) |
O1—C1—C2—C7 | 7.5 (5) | C29—C30—C31—N3 | 3.2 (7) |
O2—C1—C2—C7 | −170.8 (3) | C29—C30—C31—C32 | −176.7 (5) |
C7—C2—C3—O3 | −178.5 (3) | C36—N4—C32—C33 | −0.5 (5) |
C1—C2—C3—O3 | 4.9 (5) | Mn2—N4—C32—C33 | 179.3 (3) |
C7—C2—C3—C4 | 0.3 (5) | C36—N4—C32—C31 | −178.2 (3) |
C1—C2—C3—C4 | −176.4 (3) | Mn2—N4—C32—C31 | 1.6 (4) |
O3—C3—C4—C5 | 178.9 (3) | N3—C31—C32—N4 | 10.4 (5) |
C2—C3—C4—C5 | 0.1 (5) | C30—C31—C32—N4 | −169.7 (4) |
C3—C4—C5—C6 | 0.0 (5) | N3—C31—C32—C33 | −167.3 (4) |
C4—C5—C6—C7 | −0.4 (4) | C30—C31—C32—C33 | 12.6 (7) |
C4—C5—C6—C8 | 176.6 (3) | N4—C32—C33—C34 | 1.2 (7) |
C5—C6—C7—C2 | 0.7 (4) | C31—C32—C33—C34 | 178.7 (5) |
C8—C6—C7—C2 | −176.2 (3) | C32—C33—C34—C35 | −0.8 (9) |
C3—C2—C7—C6 | −0.7 (4) | C33—C34—C35—C36 | −0.2 (8) |
C1—C2—C7—C6 | 176.0 (3) | C32—N4—C36—C35 | −0.5 (5) |
Mn2ii—O4—C8—O5 | 6.0 (5) | Mn2—N4—C36—C35 | 179.7 (3) |
Mn2ii—O4—C8—C6 | −172.75 (19) | C34—C35—C36—N4 | 0.8 (7) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2 | 0.82 | 1.84 | 2.557 (4) | 146 |
O8—H8···O7 | 0.82 | 1.83 | 2.553 (4) | 147 |