metal-organic compounds
The mononuclear title compound, [Mn(C7H5O5S)2(C12H8N2)2], was obtained as a second crop of crystals from the hydrothermal reaction of manganese sulfate, potassium hydrogen 4-carboxybenzenesulfonate and 1,10-phenanthroline. The coordination geometry of the MnII atom is octahedral; each 4-carboxybenzenesulfonate anion retains a proton on the carboxyl group as each coordinates to the metal atom through only one sulfonyl O atom. Intermolecular π–π interactions and hydrogen bonds are observed in the crystal structure.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008020/ng6119sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008020/ng6119Isup2.hkl |
CCDC reference: 270493
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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Bis(4-carboxybenzenesulfonato)bis(1,10-phenanthroline)manganese(II) top
Crystal data top
[Mn(C7H5O5S)2(C12H8N2)2] | Z = 2 |
Mr = 817.69 | F(000) = 838 |
Triclinic, P1 | Dx = 1.591 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5218 (6) Å | Cell parameters from 3743 reflections |
b = 13.5515 (8) Å | θ = 2.4–28.0° |
c = 13.6083 (8) Å | µ = 0.58 mm−1 |
α = 89.216 (1)° | T = 295 K |
β = 78.692 (1)° | Block, pale yellow |
γ = 82.348 (1)° | 0.35 × 0.22 × 0.17 mm |
V = 1706.38 (18) Å3 |
Data collection top
Bruker APEX area-detector diffractometer | 5920 independent reflections |
Radiation source: fine-focus sealed tube | 5509 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→11 |
Tmin = 0.823, Tmax = 0.908 | k = −16→14 |
9038 measured reflections | l = −16→14 |
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)] = 0.072 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.25 | w = 1/[σ2(Fo2) + (0.0374P)2 + 2.6715P] where P = (Fo2 + 2Fc2)/3 |
5920 reflections | (Δ/σ)max = 0.001 |
502 parameters | Δρmax = 0.61 e Å−3 |
2 restraints | Δρmin = −0.33 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.13658 (7) | 0.27361 (4) | 0.72921 (5) | 0.03434 (19) | |
S1 | 0.47532 (12) | 0.31021 (8) | 0.60750 (8) | 0.0385 (3) | |
S2 | 0.25572 (14) | 0.17342 (8) | 0.93506 (9) | 0.0469 (3) | |
N1 | 0.0760 (4) | 0.4297 (2) | 0.7897 (2) | 0.0375 (8) | |
N2 | −0.0143 (3) | 0.3545 (2) | 0.6337 (2) | 0.0343 (8) | |
N3 | −0.0419 (4) | 0.1879 (2) | 0.8020 (3) | 0.0379 (8) | |
N4 | 0.1616 (4) | 0.1258 (2) | 0.6394 (3) | 0.0378 (8) | |
O1 | 0.3189 (4) | 0.3085 (3) | 0.6285 (3) | 0.0622 (10) | |
O2 | 0.5142 (3) | 0.3572 (2) | 0.5116 (2) | 0.0487 (8) | |
O3 | 0.5567 (4) | 0.2154 (2) | 0.6160 (3) | 0.0652 (10) | |
O4 | 0.5417 (4) | 0.6778 (3) | 0.9123 (3) | 0.0605 (9) | |
O5 | 0.6826 (4) | 0.5553 (3) | 0.9694 (3) | 0.0636 (10) | |
O6 | 0.2387 (4) | 0.2460 (2) | 0.8567 (3) | 0.0615 (10) | |
O7 | 0.1271 (5) | 0.1715 (3) | 1.0082 (3) | 0.0792 (12) | |
O8 | 0.3828 (4) | 0.1822 (3) | 0.9746 (3) | 0.0720 (12) | |
O9 | 0.4677 (4) | −0.2229 (3) | 0.6320 (3) | 0.0625 (10) | |
O10 | 0.2453 (4) | −0.2546 (3) | 0.6940 (3) | 0.0666 (10) | |
C1 | 0.5077 (4) | 0.3913 (3) | 0.6992 (3) | 0.0340 (9) | |
C2 | 0.4522 (5) | 0.4902 (3) | 0.7009 (3) | 0.0447 (11) | |
H2 | 0.3974 | 0.5147 | 0.6542 | 0.054* | |
C3 | 0.4782 (5) | 0.5534 (3) | 0.7724 (3) | 0.0436 (11) | |
H3 | 0.4388 | 0.6201 | 0.7748 | 0.052* | |
C4 | 0.5620 (4) | 0.5179 (3) | 0.8399 (3) | 0.0343 (9) | |
C5 | 0.6170 (5) | 0.4193 (3) | 0.8374 (3) | 0.0497 (12) | |
H5 | 0.6735 | 0.3951 | 0.8832 | 0.060* | |
C6 | 0.5894 (5) | 0.3549 (3) | 0.7672 (3) | 0.0474 (11) | |
H6 | 0.6261 | 0.2877 | 0.7663 | 0.057* | |
C7 | 0.6029 (5) | 0.5837 (3) | 0.9145 (3) | 0.0428 (11) | |
C8 | 0.2896 (5) | 0.0576 (3) | 0.8698 (3) | 0.0345 (9) | |
C9 | 0.4130 (5) | 0.0371 (3) | 0.7970 (3) | 0.0483 (11) | |
H9 | 0.4813 | 0.0811 | 0.7851 | 0.058* | |
C10 | 0.4326 (5) | −0.0513 (4) | 0.7419 (3) | 0.0501 (12) | |
H10 | 0.5161 | −0.0671 | 0.6935 | 0.060* | |
C11 | 0.3302 (5) | −0.1154 (3) | 0.7582 (3) | 0.0405 (10) | |
C12 | 0.2091 (5) | −0.0936 (3) | 0.8310 (3) | 0.0461 (11) | |
H12 | 0.1401 | −0.1372 | 0.8425 | 0.055* | |
C13 | 0.1890 (5) | −0.0084 (3) | 0.8870 (3) | 0.0416 (10) | |
H13 | 0.1070 | 0.0054 | 0.9370 | 0.050* | |
C14 | 0.3423 (5) | −0.2059 (3) | 0.6913 (3) | 0.0457 (11) | |
C15 | 0.1257 (5) | 0.4679 (4) | 0.8635 (3) | 0.0510 (12) | |
H15 | 0.1870 | 0.4263 | 0.8963 | 0.061* | |
C16 | 0.0903 (6) | 0.5669 (4) | 0.8938 (4) | 0.0584 (14) | |
H16 | 0.1276 | 0.5905 | 0.9458 | 0.070* | |
C17 | 0.0010 (6) | 0.6292 (3) | 0.8474 (4) | 0.0545 (13) | |
H17 | −0.0236 | 0.6955 | 0.8676 | 0.065* | |
C18 | −0.0540 (5) | 0.5928 (3) | 0.7686 (3) | 0.0426 (11) | |
C19 | −0.1499 (5) | 0.6516 (3) | 0.7159 (4) | 0.0549 (13) | |
H19 | −0.1800 | 0.7180 | 0.7346 | 0.066* | |
C20 | −0.1982 (5) | 0.6139 (4) | 0.6399 (4) | 0.0544 (13) | |
H20 | −0.2613 | 0.6543 | 0.6075 | 0.065* | |
C21 | −0.1540 (4) | 0.5127 (3) | 0.6084 (3) | 0.0422 (10) | |
C22 | −0.1996 (5) | 0.4695 (4) | 0.5285 (4) | 0.0509 (12) | |
H22 | −0.2619 | 0.5071 | 0.4933 | 0.061* | |
C23 | −0.1521 (5) | 0.3726 (4) | 0.5031 (3) | 0.0486 (12) | |
H23 | −0.1808 | 0.3431 | 0.4503 | 0.058* | |
C24 | −0.0603 (5) | 0.3184 (3) | 0.5570 (3) | 0.0441 (11) | |
H24 | −0.0285 | 0.2522 | 0.5385 | 0.053* | |
C25 | −0.0116 (4) | 0.4917 (3) | 0.7415 (3) | 0.0339 (9) | |
C26 | −0.0616 (4) | 0.4514 (3) | 0.6596 (3) | 0.0337 (9) | |
C27 | −0.1383 (5) | 0.2169 (4) | 0.8844 (3) | 0.0483 (11) | |
H27 | −0.1314 | 0.2762 | 0.9157 | 0.058* | |
C28 | −0.2491 (5) | 0.1624 (4) | 0.9260 (4) | 0.0572 (13) | |
H28 | −0.3161 | 0.1859 | 0.9828 | 0.069* | |
C29 | −0.2578 (5) | 0.0748 (4) | 0.8825 (4) | 0.0559 (13) | |
H29 | −0.3310 | 0.0375 | 0.9097 | 0.067* | |
C30 | −0.1573 (5) | 0.0400 (3) | 0.7968 (4) | 0.0467 (11) | |
C31 | −0.1546 (6) | −0.0543 (4) | 0.7495 (4) | 0.0625 (15) | |
H31 | −0.2241 | −0.0950 | 0.7754 | 0.075* | |
C32 | −0.0542 (6) | −0.0849 (4) | 0.6691 (4) | 0.0594 (14) | |
H32 | −0.0565 | −0.1458 | 0.6392 | 0.071* | |
C33 | 0.0569 (5) | −0.0264 (3) | 0.6279 (3) | 0.0441 (11) | |
C34 | 0.1691 (6) | −0.0578 (3) | 0.5471 (3) | 0.0483 (12) | |
H34 | 0.1724 | −0.1188 | 0.5158 | 0.058* | |
C35 | 0.2727 (5) | 0.0010 (3) | 0.5148 (3) | 0.0499 (12) | |
H35 | 0.3481 | −0.0194 | 0.4615 | 0.060* | |
C36 | 0.2647 (5) | 0.0927 (3) | 0.5626 (3) | 0.0464 (11) | |
H36 | 0.3359 | 0.1328 | 0.5391 | 0.056* | |
C37 | −0.0513 (4) | 0.1005 (3) | 0.7584 (3) | 0.0371 (10) | |
C38 | 0.0576 (5) | 0.0665 (3) | 0.6722 (3) | 0.0357 (9) | |
H4o | 0.570 (6) | 0.714 (3) | 0.953 (3) | 0.080* | |
H9o | 0.462 (6) | −0.270 (3) | 0.594 (3) | 0.080* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0386 (4) | 0.0263 (3) | 0.0390 (4) | −0.0036 (3) | −0.0095 (3) | −0.0085 (3) |
S1 | 0.0420 (6) | 0.0325 (5) | 0.0414 (6) | −0.0094 (4) | −0.0052 (5) | −0.0126 (5) |
S2 | 0.0645 (8) | 0.0344 (6) | 0.0440 (7) | 0.0050 (5) | −0.0230 (6) | −0.0150 (5) |
N1 | 0.044 (2) | 0.0318 (18) | 0.037 (2) | −0.0041 (15) | −0.0089 (16) | −0.0073 (15) |
N2 | 0.0351 (19) | 0.0334 (18) | 0.0335 (18) | −0.0045 (15) | −0.0045 (15) | −0.0031 (15) |
N3 | 0.036 (2) | 0.038 (2) | 0.039 (2) | 0.0009 (15) | −0.0093 (16) | −0.0006 (16) |
N4 | 0.039 (2) | 0.0350 (19) | 0.040 (2) | −0.0048 (16) | −0.0096 (17) | −0.0035 (16) |
O1 | 0.049 (2) | 0.077 (2) | 0.061 (2) | −0.0291 (18) | 0.0042 (17) | −0.0233 (18) |
O2 | 0.060 (2) | 0.0492 (18) | 0.0377 (17) | −0.0145 (15) | −0.0058 (15) | −0.0129 (14) |
O3 | 0.090 (3) | 0.0371 (18) | 0.071 (2) | 0.0028 (18) | −0.029 (2) | −0.0159 (16) |
O4 | 0.072 (2) | 0.052 (2) | 0.065 (2) | −0.0044 (18) | −0.0309 (19) | −0.0261 (17) |
O5 | 0.074 (2) | 0.075 (2) | 0.051 (2) | −0.0066 (19) | −0.0350 (19) | −0.0143 (18) |
O6 | 0.090 (3) | 0.0392 (18) | 0.068 (2) | −0.0058 (17) | −0.048 (2) | −0.0043 (16) |
O7 | 0.093 (3) | 0.066 (2) | 0.064 (2) | 0.007 (2) | 0.011 (2) | −0.031 (2) |
O8 | 0.095 (3) | 0.051 (2) | 0.082 (3) | 0.0105 (19) | −0.059 (2) | −0.0293 (19) |
O9 | 0.074 (3) | 0.057 (2) | 0.053 (2) | 0.0002 (19) | −0.0078 (19) | −0.0237 (17) |
O10 | 0.077 (3) | 0.052 (2) | 0.073 (3) | −0.0165 (19) | −0.015 (2) | −0.0163 (18) |
C1 | 0.033 (2) | 0.037 (2) | 0.031 (2) | −0.0077 (18) | −0.0024 (17) | −0.0048 (17) |
C2 | 0.060 (3) | 0.031 (2) | 0.051 (3) | −0.002 (2) | −0.032 (2) | −0.004 (2) |
C3 | 0.055 (3) | 0.030 (2) | 0.050 (3) | −0.003 (2) | −0.022 (2) | −0.0065 (19) |
C4 | 0.038 (2) | 0.039 (2) | 0.026 (2) | −0.0082 (18) | −0.0041 (17) | −0.0057 (17) |
C5 | 0.064 (3) | 0.048 (3) | 0.040 (3) | 0.004 (2) | −0.026 (2) | −0.004 (2) |
C6 | 0.059 (3) | 0.034 (2) | 0.050 (3) | 0.006 (2) | −0.019 (2) | −0.007 (2) |
C7 | 0.046 (3) | 0.049 (3) | 0.034 (2) | −0.012 (2) | −0.004 (2) | −0.009 (2) |
C8 | 0.045 (2) | 0.030 (2) | 0.029 (2) | 0.0020 (18) | −0.0122 (18) | −0.0066 (17) |
C9 | 0.050 (3) | 0.048 (3) | 0.047 (3) | −0.014 (2) | −0.006 (2) | −0.009 (2) |
C10 | 0.043 (3) | 0.062 (3) | 0.040 (3) | 0.006 (2) | −0.002 (2) | −0.015 (2) |
C11 | 0.053 (3) | 0.033 (2) | 0.038 (2) | −0.001 (2) | −0.019 (2) | −0.0025 (18) |
C12 | 0.058 (3) | 0.042 (3) | 0.042 (3) | −0.012 (2) | −0.015 (2) | 0.000 (2) |
C13 | 0.050 (3) | 0.040 (2) | 0.033 (2) | −0.001 (2) | −0.006 (2) | −0.0055 (19) |
C14 | 0.053 (3) | 0.041 (3) | 0.044 (3) | −0.004 (2) | −0.015 (2) | 0.004 (2) |
C15 | 0.063 (3) | 0.049 (3) | 0.043 (3) | −0.009 (2) | −0.017 (2) | −0.009 (2) |
C16 | 0.083 (4) | 0.046 (3) | 0.048 (3) | −0.022 (3) | −0.008 (3) | −0.019 (2) |
C17 | 0.066 (3) | 0.034 (2) | 0.057 (3) | −0.010 (2) | 0.007 (3) | −0.015 (2) |
C18 | 0.044 (3) | 0.028 (2) | 0.048 (3) | −0.0063 (19) | 0.010 (2) | −0.0058 (19) |
C19 | 0.048 (3) | 0.028 (2) | 0.078 (4) | 0.003 (2) | 0.011 (3) | 0.005 (2) |
C20 | 0.041 (3) | 0.042 (3) | 0.075 (4) | 0.000 (2) | −0.005 (3) | 0.015 (3) |
C21 | 0.028 (2) | 0.046 (3) | 0.049 (3) | −0.0041 (19) | −0.0005 (19) | 0.011 (2) |
C22 | 0.039 (3) | 0.064 (3) | 0.052 (3) | −0.009 (2) | −0.015 (2) | 0.015 (2) |
C23 | 0.038 (3) | 0.068 (3) | 0.044 (3) | −0.017 (2) | −0.012 (2) | 0.001 (2) |
C24 | 0.047 (3) | 0.045 (3) | 0.042 (3) | −0.010 (2) | −0.009 (2) | −0.009 (2) |
C25 | 0.031 (2) | 0.031 (2) | 0.036 (2) | −0.0055 (17) | 0.0027 (17) | −0.0021 (17) |
C26 | 0.028 (2) | 0.034 (2) | 0.037 (2) | −0.0077 (17) | 0.0009 (17) | 0.0002 (17) |
C27 | 0.045 (3) | 0.050 (3) | 0.047 (3) | 0.012 (2) | −0.014 (2) | −0.005 (2) |
C28 | 0.043 (3) | 0.075 (4) | 0.046 (3) | 0.010 (3) | −0.003 (2) | 0.011 (3) |
C29 | 0.043 (3) | 0.066 (3) | 0.061 (3) | −0.011 (2) | −0.015 (2) | 0.018 (3) |
C30 | 0.045 (3) | 0.051 (3) | 0.047 (3) | −0.010 (2) | −0.016 (2) | 0.012 (2) |
C31 | 0.071 (4) | 0.050 (3) | 0.076 (4) | −0.032 (3) | −0.021 (3) | 0.012 (3) |
C32 | 0.084 (4) | 0.041 (3) | 0.063 (3) | −0.028 (3) | −0.025 (3) | 0.005 (2) |
C33 | 0.061 (3) | 0.032 (2) | 0.047 (3) | −0.009 (2) | −0.026 (2) | 0.0008 (19) |
C34 | 0.073 (3) | 0.034 (2) | 0.043 (3) | −0.007 (2) | −0.024 (2) | −0.009 (2) |
C35 | 0.061 (3) | 0.044 (3) | 0.044 (3) | −0.001 (2) | −0.010 (2) | −0.009 (2) |
C36 | 0.046 (3) | 0.041 (3) | 0.051 (3) | −0.010 (2) | −0.004 (2) | −0.006 (2) |
C37 | 0.039 (2) | 0.035 (2) | 0.042 (2) | −0.0047 (18) | −0.0169 (19) | 0.0040 (19) |
C38 | 0.042 (2) | 0.034 (2) | 0.036 (2) | −0.0055 (18) | −0.0192 (19) | 0.0026 (18) |
Geometric parameters (Å, º) top
Mn1—O1 | 2.094 (3) | C11—C12 | 1.366 (6) |
Mn1—O6 | 2.155 (3) | C11—C14 | 1.516 (6) |
Mn1—N1 | 2.241 (3) | C12—C13 | 1.363 (6) |
Mn1—N2 | 2.287 (3) | C12—H12 | 0.9300 |
Mn1—N3 | 2.248 (4) | C13—H13 | 0.9300 |
Mn1—N4 | 2.321 (3) | C15—C16 | 1.387 (6) |
S1—O3 | 1.425 (3) | C15—H15 | 0.9300 |
S1—O2 | 1.448 (3) | C16—C17 | 1.356 (7) |
S1—O1 | 1.464 (3) | C16—H16 | 0.9300 |
S1—C1 | 1.772 (4) | C17—C18 | 1.404 (7) |
S2—O7 | 1.421 (4) | C17—H17 | 0.9300 |
S2—O8 | 1.436 (4) | C18—C25 | 1.408 (5) |
S2—O6 | 1.459 (3) | C18—C19 | 1.425 (7) |
S2—C8 | 1.774 (4) | C19—C20 | 1.343 (7) |
N1—C15 | 1.330 (5) | C19—H19 | 0.9300 |
N1—C25 | 1.358 (5) | C20—C21 | 1.426 (6) |
N2—C24 | 1.330 (5) | C20—H20 | 0.9300 |
N2—C26 | 1.358 (5) | C21—C26 | 1.408 (6) |
N3—C27 | 1.330 (6) | C21—C22 | 1.409 (7) |
N3—C37 | 1.353 (5) | C22—C23 | 1.357 (7) |
N4—C36 | 1.323 (5) | C22—H22 | 0.9300 |
N4—C38 | 1.362 (5) | C23—C24 | 1.380 (6) |
O4—C7 | 1.332 (6) | C23—H23 | 0.9300 |
O4—H4O | 0.85 (5) | C24—H24 | 0.9300 |
O5—C7 | 1.191 (5) | C25—C26 | 1.435 (6) |
O9—C14 | 1.297 (6) | C27—C28 | 1.393 (7) |
O9—H9O | 0.84 (4) | C27—H27 | 0.9300 |
O10—C14 | 1.200 (5) | C28—C29 | 1.354 (7) |
C1—C6 | 1.368 (6) | C28—H28 | 0.9300 |
C1—C2 | 1.373 (6) | C29—C30 | 1.398 (7) |
C2—C3 | 1.384 (6) | C29—H29 | 0.9300 |
C2—H2 | 0.9300 | C30—C37 | 1.403 (6) |
C3—C4 | 1.372 (6) | C30—C31 | 1.434 (7) |
C3—H3 | 0.9300 | C31—C32 | 1.334 (8) |
C4—C5 | 1.367 (6) | C31—H31 | 0.9300 |
C4—C7 | 1.500 (6) | C32—C33 | 1.428 (7) |
C5—C6 | 1.388 (6) | C32—H32 | 0.9300 |
C5—H5 | 0.9300 | C33—C34 | 1.401 (7) |
C6—H6 | 0.9300 | C33—C38 | 1.404 (6) |
C8—C9 | 1.379 (6) | C34—C35 | 1.353 (7) |
C8—C13 | 1.381 (6) | C34—H34 | 0.9300 |
C9—C10 | 1.394 (6) | C35—C36 | 1.397 (6) |
C9—H9 | 0.9300 | C35—H35 | 0.9300 |
C10—C11 | 1.375 (6) | C36—H36 | 0.9300 |
C10—H10 | 0.9300 | C37—C38 | 1.440 (6) |
O1—Mn1—O6 | 97.0 (2) | C12—C13—C8 | 120.4 (4) |
O1—Mn1—N1 | 93.4 (1) | C12—C13—H13 | 119.8 |
O1—Mn1—N2 | 91.4 (1) | C8—C13—H13 | 119.8 |
O1—Mn1—N3 | 159.6 (1) | O10—C14—O9 | 125.1 (5) |
O1—Mn1—N4 | 87.1 (1) | O10—C14—C11 | 122.7 (5) |
O6—Mn1—N1 | 85.4 (1) | O9—C14—C11 | 112.2 (4) |
O6—Mn1—N2 | 157.5 (1) | N1—C15—C16 | 122.9 (5) |
O6—Mn1—N3 | 89.8 (1) | N1—C15—H15 | 118.5 |
O6—Mn1—N4 | 108.7 (1) | C16—C15—H15 | 118.5 |
N1—Mn1—N2 | 73.2 (1) | C17—C16—C15 | 119.8 (5) |
N1—Mn1—N3 | 106.4 (1) | C17—C16—H16 | 120.1 |
N1—Mn1—N4 | 165.7 (1) | C15—C16—H16 | 120.1 |
N2—Mn1—N3 | 89.5 (1) | C16—C17—C18 | 119.6 (4) |
N2—Mn1—N4 | 92.5 (1) | C16—C17—H17 | 120.2 |
N3—Mn1—N4 | 72.4 (1) | C18—C17—H17 | 120.2 |
O3—S1—O2 | 114.2 (2) | C17—C18—C25 | 117.2 (4) |
O3—S1—O1 | 113.6 (2) | C17—C18—C19 | 124.0 (4) |
O2—S1—O1 | 108.2 (2) | C25—C18—C19 | 118.8 (4) |
O3—S1—C1 | 108.3 (2) | C20—C19—C18 | 121.8 (4) |
O2—S1—C1 | 106.6 (2) | C20—C19—H19 | 119.1 |
O1—S1—C1 | 105.5 (2) | C18—C19—H19 | 119.1 |
O7—S2—O8 | 115.1 (3) | C19—C20—C21 | 120.9 (5) |
O7—S2—O6 | 112.9 (2) | C19—C20—H20 | 119.6 |
O8—S2—O6 | 111.3 (2) | C21—C20—H20 | 119.6 |
O7—S2—C8 | 106.8 (2) | C26—C21—C22 | 117.4 (4) |
O8—S2—C8 | 106.2 (2) | C26—C21—C20 | 119.2 (4) |
O6—S2—C8 | 103.4 (2) | C22—C21—C20 | 123.4 (4) |
C15—N1—C25 | 117.8 (4) | C23—C22—C21 | 119.6 (4) |
C15—N1—Mn1 | 125.7 (3) | C23—C22—H22 | 120.2 |
C25—N1—Mn1 | 116.3 (3) | C21—C22—H22 | 120.2 |
C24—N2—C26 | 117.0 (4) | C22—C23—C24 | 118.9 (4) |
C24—N2—Mn1 | 128.1 (3) | C22—C23—H23 | 120.5 |
C26—N2—Mn1 | 114.9 (3) | C24—C23—H23 | 120.5 |
C27—N3—C37 | 118.0 (4) | N2—C24—C23 | 124.5 (4) |
C27—N3—Mn1 | 124.7 (3) | N2—C24—H24 | 117.8 |
C37—N3—Mn1 | 117.3 (3) | C23—C24—H24 | 117.8 |
C36—N4—C38 | 117.3 (4) | N1—C25—C18 | 122.7 (4) |
C36—N4—Mn1 | 127.9 (3) | N1—C25—C26 | 117.8 (3) |
C38—N4—Mn1 | 114.8 (3) | C18—C25—C26 | 119.5 (4) |
S1—O1—Mn1 | 147.6 (3) | N2—C26—C21 | 122.6 (4) |
C7—O4—H4O | 111 (4) | N2—C26—C25 | 117.7 (4) |
S2—O6—Mn1 | 141.8 (2) | C21—C26—C25 | 119.7 (4) |
C14—O9—H9O | 106 (4) | N3—C27—C28 | 122.9 (5) |
C6—C1—C2 | 120.5 (4) | N3—C27—H27 | 118.6 |
C6—C1—S1 | 119.6 (3) | C28—C27—H27 | 118.6 |
C2—C1—S1 | 119.9 (3) | C29—C28—C27 | 119.0 (5) |
C1—C2—C3 | 119.7 (4) | C29—C28—H28 | 120.5 |
C1—C2—H2 | 120.2 | C27—C28—H28 | 120.5 |
C3—C2—H2 | 120.2 | C28—C29—C30 | 120.3 (5) |
C4—C3—C2 | 120.2 (4) | C28—C29—H29 | 119.8 |
C4—C3—H3 | 119.9 | C30—C29—H29 | 119.8 |
C2—C3—H3 | 119.9 | C29—C30—C37 | 117.0 (4) |
C5—C4—C3 | 119.6 (4) | C29—C30—C31 | 123.7 (5) |
C5—C4—C7 | 117.5 (4) | C37—C30—C31 | 119.3 (5) |
C3—C4—C7 | 122.9 (4) | C32—C31—C30 | 121.2 (5) |
C4—C5—C6 | 120.7 (4) | C32—C31—H31 | 119.4 |
C4—C5—H5 | 119.6 | C30—C31—H31 | 119.4 |
C6—C5—H5 | 119.6 | C31—C32—C33 | 121.6 (5) |
C1—C6—C5 | 119.3 (4) | C31—C32—H32 | 119.2 |
C1—C6—H6 | 120.4 | C33—C32—H32 | 119.2 |
C5—C6—H6 | 120.4 | C34—C33—C38 | 117.5 (4) |
O5—C7—O4 | 123.4 (4) | C34—C33—C32 | 123.6 (4) |
O5—C7—C4 | 123.8 (4) | C38—C33—C32 | 118.8 (5) |
O4—C7—C4 | 112.8 (4) | C35—C34—C33 | 119.8 (4) |
C9—C8—C13 | 120.3 (4) | C35—C34—H34 | 120.1 |
C9—C8—S2 | 119.2 (3) | C33—C34—H34 | 120.1 |
C13—C8—S2 | 120.3 (3) | C34—C35—C36 | 119.0 (4) |
C8—C9—C10 | 118.3 (4) | C34—C35—H35 | 120.5 |
C8—C9—H9 | 120.9 | C36—C35—H35 | 120.5 |
C10—C9—H9 | 120.9 | N4—C36—C35 | 123.7 (4) |
C11—C10—C9 | 120.8 (4) | N4—C36—H36 | 118.1 |
C11—C10—H10 | 119.6 | C35—C36—H36 | 118.1 |
C9—C10—H10 | 119.6 | N3—C37—C30 | 122.8 (4) |
C12—C11—C10 | 119.7 (4) | N3—C37—C38 | 118.0 (4) |
C12—C11—C14 | 118.8 (4) | C30—C37—C38 | 119.2 (4) |
C10—C11—C14 | 121.3 (4) | N4—C38—C33 | 122.6 (4) |
C13—C12—C11 | 120.3 (4) | N4—C38—C37 | 117.4 (4) |
C13—C12—H12 | 119.8 | C33—C38—C37 | 120.0 (4) |
C11—C12—H12 | 119.8 | ||
O1—Mn1—N1—C15 | −86.3 (4) | C9—C10—C11—C12 | −1.6 (7) |
O6—Mn1—N1—C15 | 10.4 (4) | C9—C10—C11—C14 | 173.2 (4) |
N3—Mn1—N1—C15 | 98.9 (4) | C10—C11—C12—C13 | 0.5 (7) |
N2—Mn1—N1—C15 | −176.7 (4) | C14—C11—C12—C13 | −174.5 (4) |
N4—Mn1—N1—C15 | −177.9 (5) | C11—C12—C13—C8 | 0.9 (7) |
O1—Mn1—N1—C25 | 89.0 (3) | C9—C8—C13—C12 | −1.2 (6) |
O6—Mn1—N1—C25 | −174.3 (3) | S2—C8—C13—C12 | 174.5 (3) |
N3—Mn1—N1—C25 | −85.8 (3) | C12—C11—C14—O10 | 6.4 (7) |
N2—Mn1—N1—C25 | −1.5 (3) | C10—C11—C14—O10 | −168.6 (5) |
N4—Mn1—N1—C25 | −2.7 (7) | C12—C11—C14—O9 | −174.1 (4) |
O1—Mn1—N2—C24 | 87.3 (4) | C10—C11—C14—O9 | 11.0 (6) |
O6—Mn1—N2—C24 | −160.7 (4) | C25—N1—C15—C16 | 1.0 (7) |
N1—Mn1—N2—C24 | −179.6 (4) | Mn1—N1—C15—C16 | 176.2 (4) |
N3—Mn1—N2—C24 | −72.3 (4) | N1—C15—C16—C17 | 0.0 (8) |
N4—Mn1—N2—C24 | 0.1 (4) | C15—C16—C17—C18 | −0.4 (8) |
O1—Mn1—N2—C26 | −92.7 (3) | C16—C17—C18—C25 | −0.3 (7) |
O6—Mn1—N2—C26 | 19.3 (5) | C16—C17—C18—C19 | 179.1 (5) |
N1—Mn1—N2—C26 | 0.4 (3) | C17—C18—C19—C20 | 179.1 (5) |
N3—Mn1—N2—C26 | 107.7 (3) | C25—C18—C19—C20 | −1.5 (7) |
N4—Mn1—N2—C26 | −179.9 (3) | C18—C19—C20—C21 | −0.5 (7) |
O1—Mn1—N3—C27 | 177.3 (4) | C19—C20—C21—C26 | 1.7 (7) |
O6—Mn1—N3—C27 | 67.4 (3) | C19—C20—C21—C22 | −179.2 (4) |
N1—Mn1—N3—C27 | −17.8 (4) | C26—C21—C22—C23 | −1.0 (6) |
N2—Mn1—N3—C27 | −90.1 (3) | C20—C21—C22—C23 | 179.9 (4) |
N4—Mn1—N3—C27 | 177.1 (4) | C21—C22—C23—C24 | 0.3 (7) |
O1—Mn1—N3—C37 | −2.8 (6) | C26—N2—C24—C23 | −0.1 (6) |
O6—Mn1—N3—C37 | −112.6 (3) | Mn1—N2—C24—C23 | 179.9 (3) |
N1—Mn1—N3—C37 | 162.2 (3) | C22—C23—C24—N2 | 0.2 (7) |
N2—Mn1—N3—C37 | 89.9 (3) | C15—N1—C25—C18 | −1.8 (6) |
N4—Mn1—N3—C37 | −2.9 (3) | Mn1—N1—C25—C18 | −177.4 (3) |
O1—Mn1—N4—C36 | 3.5 (4) | C15—N1—C25—C26 | 178.0 (4) |
O6—Mn1—N4—C36 | −92.9 (4) | Mn1—N1—C25—C26 | 2.4 (5) |
N1—Mn1—N4—C36 | 95.9 (6) | C17—C18—C25—N1 | 1.5 (6) |
N3—Mn1—N4—C36 | −176.6 (4) | C19—C18—C25—N1 | −178.0 (4) |
N2—Mn1—N4—C36 | 94.7 (4) | C17—C18—C25—C26 | −178.4 (4) |
O1—Mn1—N4—C38 | −177.7 (3) | C19—C18—C25—C26 | 2.2 (6) |
O6—Mn1—N4—C38 | 85.9 (3) | C24—N2—C26—C21 | −0.6 (6) |
N1—Mn1—N4—C38 | −85.3 (6) | Mn1—N2—C26—C21 | 179.4 (3) |
N3—Mn1—N4—C38 | 2.3 (3) | C24—N2—C26—C25 | −179.3 (4) |
N2—Mn1—N4—C38 | −86.4 (3) | Mn1—N2—C26—C25 | 0.7 (4) |
O3—S1—O1—Mn1 | 55.9 (4) | C22—C21—C26—N2 | 1.2 (6) |
O2—S1—O1—Mn1 | −176.2 (4) | C20—C21—C26—N2 | −179.7 (4) |
C1—S1—O1—Mn1 | −62.5 (4) | C22—C21—C26—C25 | 179.8 (4) |
O6—Mn1—O1—S1 | 10.8 (4) | C20—C21—C26—C25 | −1.0 (6) |
N1—Mn1—O1—S1 | 96.6 (4) | N1—C25—C26—N2 | −2.1 (5) |
N3—Mn1—O1—S1 | −97.9 (5) | C18—C25—C26—N2 | 177.8 (4) |
N2—Mn1—O1—S1 | 169.8 (4) | N1—C25—C26—C21 | 179.2 (4) |
N4—Mn1—O1—S1 | −97.7 (4) | C18—C25—C26—C21 | −1.0 (6) |
O7—S2—O6—Mn1 | −70.9 (4) | C37—N3—C27—C28 | −1.3 (6) |
O8—S2—O6—Mn1 | 157.8 (3) | Mn1—N3—C27—C28 | 178.7 (3) |
C8—S2—O6—Mn1 | 44.1 (4) | N3—C27—C28—C29 | 1.6 (7) |
O1—Mn1—O6—S2 | −130.9 (4) | C27—C28—C29—C30 | −0.3 (7) |
N1—Mn1—O6—S2 | 136.2 (4) | C28—C29—C30—C37 | −1.2 (7) |
N3—Mn1—O6—S2 | 29.8 (4) | C28—C29—C30—C31 | 176.6 (5) |
N2—Mn1—O6—S2 | 118.1 (4) | C29—C30—C31—C32 | −178.5 (5) |
N4—Mn1—O6—S2 | −41.6 (4) | C37—C30—C31—C32 | −0.8 (8) |
O3—S1—C1—C6 | −5.2 (4) | C30—C31—C32—C33 | 1.4 (8) |
O2—S1—C1—C6 | −128.5 (4) | C31—C32—C33—C34 | 176.3 (5) |
O1—S1—C1—C6 | 116.7 (4) | C31—C32—C33—C38 | −1.4 (7) |
O3—S1—C1—C2 | 174.1 (4) | C38—C33—C34—C35 | 0.0 (6) |
O2—S1—C1—C2 | 50.8 (4) | C32—C33—C34—C35 | −177.8 (5) |
O1—S1—C1—C2 | −64.0 (4) | C33—C34—C35—C36 | −0.5 (7) |
C6—C1—C2—C3 | −0.5 (7) | C38—N4—C36—C35 | −0.6 (7) |
S1—C1—C2—C3 | −179.8 (4) | Mn1—N4—C36—C35 | 178.2 (3) |
C1—C2—C3—C4 | 1.6 (7) | C34—C35—C36—N4 | 0.8 (7) |
C2—C3—C4—C5 | −1.4 (7) | C27—N3—C37—C30 | −0.4 (6) |
C2—C3—C4—C7 | 175.6 (4) | Mn1—N3—C37—C30 | 179.7 (3) |
C3—C4—C5—C6 | 0.2 (7) | C27—N3—C37—C38 | −176.8 (4) |
C7—C4—C5—C6 | −176.9 (4) | Mn1—N3—C37—C38 | 3.3 (5) |
C2—C1—C6—C5 | −0.7 (7) | C29—C30—C37—N3 | 1.6 (6) |
S1—C1—C6—C5 | 178.6 (4) | C31—C30—C37—N3 | −176.3 (4) |
C4—C5—C6—C1 | 0.8 (7) | C29—C30—C37—C38 | 177.9 (4) |
C5—C4—C7—O5 | 1.8 (7) | C31—C30—C37—C38 | 0.1 (6) |
C3—C4—C7—O5 | −175.3 (5) | C36—N4—C38—C33 | 0.0 (6) |
C5—C4—C7—O4 | −178.8 (4) | Mn1—N4—C38—C33 | −179.0 (3) |
C3—C4—C7—O4 | 4.2 (6) | C36—N4—C38—C37 | 177.5 (4) |
O7—S2—C8—C9 | −176.9 (4) | Mn1—N4—C38—C37 | −1.5 (4) |
O8—S2—C8—C9 | −53.6 (4) | C34—C33—C38—N4 | 0.3 (6) |
O6—S2—C8—C9 | 63.7 (4) | C32—C33—C38—N4 | 178.2 (4) |
O7—S2—C8—C13 | 7.4 (4) | C34—C33—C38—C37 | −177.2 (4) |
O8—S2—C8—C13 | 130.7 (4) | C32—C33—C38—C37 | 0.7 (6) |
O6—S2—C8—C13 | −112.0 (4) | N3—C37—C38—N4 | −1.1 (5) |
C13—C8—C9—C10 | 0.1 (7) | C30—C37—C38—N4 | −177.7 (4) |
S2—C8—C9—C10 | −175.7 (3) | N3—C37—C38—C33 | 176.4 (4) |
C8—C9—C10—C11 | 1.3 (7) | C30—C37—C38—C33 | −0.1 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4o···O8i | 0.85 (5) | 1.88 (4) | 2.713 (4) | 168 (6) |
O9—H9o···O2ii | 0.84 (4) | 1.83 (4) | 2.653 (4) | 165 (6) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+1. |