metal-organic compounds
Bis(ethanamidinium) (1,10-phenanthroline-2,9-dicarboxylato)manganate(II) heptahydrate
aCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
*Correspondence e-mail: myl9831@163.com
In the title complex, (C2H7N2)2[Mn(C14H6N2O4)2]·7H2O, the MnII atom is coordinated by four N atoms and four O atoms from two 1,10-phenanthroline-2,9-dicarboxylate ligands in a distorted dodecahedral geometry. The double negative charge is balanced by two ethanamidinium cations. A three-dimensional supramolecular structure is formed through N—H⋯O and O—H⋯O hydrogen bonds and π–π stacking interactions [centroid–centroid distance = 3.553 (2) Å].
Related literature
For general background to 1,10-phenanthroline derivatives, see: Kaes et al. (2000); Albores & Rentschler (2008); Sreerama & Pal (2004) and to 1,10-phenanthroline-2,9-dicarboxylate (H2phenda), see: Dean et al. (2008); Gephart et al. (2008); Moghimi et al. (2005); Fan et al. (2008). For the synthesis, see: Chandler et al. (1981).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536812048350/fi2126sup1.cif
contains datablocks I, global. DOI:Supporting information file. DOI: https://doi.org/10.1107/S1600536812048350/fi2126Isup2.cdx
Supporting information file. DOI: https://doi.org/10.1107/S1600536812048350/fi2126Isup4.cdx
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812048350/fi2126Isup3.hkl
Hydrothermal treatment of manganese chloride tetrahydrate (0.2 mmol, 0.039 g), 1,10-phenanthroline-2,9-dicarboxylate (0.2 mmol, 0.054 g) synthesized according to C. J. Chandler et al. (1981), triethylamine (0.080 g, 0.4 mmol), and methanol/acetonitrile (15 ml,V/V = 5/1) over 72 h at 418 K yielded light yellow block-shaped crystals.
Diffraction data for compound I were recorded on Oxford Diffraction Gemini R CCD diffractometer at 150 (2) K. The data collection routine,
and data processing were carried out with the program CrysAlis PRO for I.All H atoms were placed in idealized positions, and were refined using as riding model with C—H distances of 0.95, 0.98, 0.90 and 0.85 Å, for aryl, methyl, amido and water, respectively, with Uiso(H) = 1.5Ueq (methyl C-atoms) and 1.2Ueq(non-methyl C-atoms). The hightest peak is located 1.13 Å from O5W and the deepest hole is located 0.68 Å from N5.
1,10-Phenanthroline and its substituted derivatives have versatile chelating and bridging capability(Kaes et al., 2000; Albores & Rentschler, 2008) which have played an important role in the development of coordination chemistry while the oxime, similar to the cyanide, can link two
carriers with the shortest pairwise exchange pathway (Sreerama & Pal, 2004). Preliminary study on the coordination chemistry of 1,10-phenanthroline-2,9-dicarboxylate (H2phenda) found that it chelates the metal ions such as Ca(II), Cu(II), Th(III), Eu(III) and Tb(III) as a tridentate or tetradentate ligand by the phenanthroline and one or both of the oxygen atoms on the carboxylate groups (Dean et al., 2008; Gephart et al., 2008; Moghimi et al., 2005; Fan et al., 2008). We report here the of the title compound, (I).The title compound is ionic and contains discrete 1,10-phenanthroline- 2,9-dicarboxylate manganese(II) anions, ethanamidinium cations and water molecules (Fig. 1). The Mn atom is coordinated by four N atoms and four O atoms from two 1,10-phenanthroline-2,9-dicarboxylate ligands in a distorted dodecahedron geometry.
In the π-π interactions (Figure 2) between the neighboring aromatic rings of phenda ligands link the molecules into an infinite layer. The centroid to centroid distance between pyridine rings is 3.553 (2) Å. The crystal packing is further stabilized by N—H···O and O—H···O hydrogen bonds (Table 1 and Figure 3), which link the layers into a three dimensional framework (Figure 4).
intermolecularFor general background to 1,10-phenanthroline derivatives, see: Kaes et al. (2000); Albores & Rentschler (2008); Sreerama & Pal (2004) and to 1,10-phenanthroline-2,9-dicarboxylate (H2phenda) see: Dean et al. (2008); Gephart et al. (2008); Moghimi et al. (2005); Fan et al. (2008). For the synthesis, see: Chandler et al. (1981).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell
CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. | |
Fig. 2. The off-set π-π stacking interaction in the distance of 3.553 (2) Å between phenda2- groups from the neighboring units (the H-atoms on the phenda2- are omitted for clarity) | |
Fig. 3. A perspective view of hydrogen bonding interactions shown as dashed lines. | |
Fig. 4. The three-dimensional framework of the title compound through intermolecular π-π stacking interactions and all hydrogen bonds. |
(C2H7N2)2[Mn(C14H6N2O4)2]·7H2O | Z = 2 |
Mr = 831.66 | F(000) = 866 |
Triclinic, P1 | Dx = 1.522 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54178 Å |
a = 9.6330 (6) Å | Cell parameters from 2456 reflections |
b = 13.8174 (7) Å | θ = 3.8–60.5° |
c = 15.4828 (8) Å | µ = 3.69 mm−1 |
α = 66.151 (5)° | T = 150 K |
β = 78.949 (5)° | Block, yellow |
γ = 75.397 (5)° | 0.29 × 0.26 × 0.16 mm |
V = 1814.56 (19) Å3 |
Agilent Gemini S Ultra CCD diffractometer | 5310 independent reflections |
Radiation source: Ultra (Cu) X-ray Source | 4336 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.024 |
ω and ψ scan | θmax = 60.0°, θmin = 3.1° |
Absorption correction: multi-scan (Blessing, 1995) | h = −10→10 |
Tmin = 0.395, Tmax = 0.554 | k = −15→15 |
10581 measured reflections | l = −17→17 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0694P)2] where P = (Fo2 + 2Fc2)/3 |
5310 reflections | (Δ/σ)max < 0.001 |
507 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
(C2H7N2)2[Mn(C14H6N2O4)2]·7H2O | γ = 75.397 (5)° |
Mr = 831.66 | V = 1814.56 (19) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.6330 (6) Å | Cu Kα radiation |
b = 13.8174 (7) Å | µ = 3.69 mm−1 |
c = 15.4828 (8) Å | T = 150 K |
α = 66.151 (5)° | 0.29 × 0.26 × 0.16 mm |
β = 78.949 (5)° |
Agilent Gemini S Ultra CCD diffractometer | 5310 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 4336 reflections with I > 2σ(I) |
Tmin = 0.395, Tmax = 0.554 | Rint = 0.024 |
10581 measured reflections | θmax = 60.0° |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.49 e Å−3 |
5310 reflections | Δρmin = −0.38 e Å−3 |
507 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.38224 (4) | −0.32469 (3) | −0.30135 (3) | 0.02456 (13) | |
O1 | 0.62034 (19) | −0.44480 (14) | −0.29790 (12) | 0.0315 (4) | |
O2 | 0.7512 (2) | −0.60690 (15) | −0.22274 (14) | 0.0405 (5) | |
O3 | 0.19195 (19) | −0.18187 (14) | −0.36856 (13) | 0.0322 (4) | |
O4 | −0.0144 (2) | −0.07603 (17) | −0.34049 (16) | 0.0526 (6) | |
O5 | 0.4381 (2) | −0.21686 (15) | −0.22559 (12) | 0.0342 (4) | |
O6 | 0.5792 (2) | −0.10790 (16) | −0.23117 (14) | 0.0429 (5) | |
O7 | 0.27142 (19) | −0.45336 (14) | −0.31506 (12) | 0.0316 (4) | |
O8 | 0.2046 (2) | −0.51264 (15) | −0.41261 (13) | 0.0352 (4) | |
N1 | 0.4178 (2) | −0.46684 (16) | −0.15591 (14) | 0.0247 (5) | |
N2 | 0.1863 (2) | −0.31304 (16) | −0.19121 (15) | 0.0266 (5) | |
N3 | 0.5253 (2) | −0.20108 (16) | −0.39983 (14) | 0.0249 (5) | |
N4 | 0.4184 (2) | −0.32404 (16) | −0.45354 (14) | 0.0238 (5) | |
C1 | 0.5334 (3) | −0.5458 (2) | −0.14235 (18) | 0.0275 (6) | |
C2 | 0.5504 (3) | −0.6328 (2) | −0.05494 (19) | 0.0327 (6) | |
H2 | 0.6323 | −0.6896 | −0.0479 | 0.039* | |
C3 | 0.4479 (3) | −0.6348 (2) | 0.01978 (19) | 0.0361 (7) | |
H3 | 0.4594 | −0.6924 | 0.0796 | 0.043* | |
C4 | 0.3259 (3) | −0.5520 (2) | 0.00840 (19) | 0.0328 (6) | |
C5 | 0.3154 (3) | −0.4703 (2) | −0.08246 (17) | 0.0264 (6) | |
C6 | 0.1906 (3) | −0.3847 (2) | −0.10117 (18) | 0.0276 (6) | |
C7 | 0.0811 (3) | −0.3796 (2) | −0.0278 (2) | 0.0355 (7) | |
C8 | −0.0404 (3) | −0.2954 (2) | −0.0534 (2) | 0.0398 (7) | |
H8 | −0.1181 | −0.2882 | −0.0069 | 0.048* | |
C9 | −0.0455 (3) | −0.2239 (2) | −0.1460 (2) | 0.0392 (7) | |
H9 | −0.1277 | −0.1681 | −0.1643 | 0.047* | |
C10 | 0.0723 (3) | −0.2344 (2) | −0.2135 (2) | 0.0317 (6) | |
C11 | 0.2133 (3) | −0.5429 (2) | 0.08190 (19) | 0.0386 (7) | |
H11 | 0.2200 | −0.5962 | 0.1442 | 0.046* | |
C12 | 0.0976 (3) | −0.4606 (2) | 0.0651 (2) | 0.0398 (7) | |
H12 | 0.0263 | −0.4567 | 0.1159 | 0.048* | |
C13 | 0.6447 (3) | −0.5317 (2) | −0.22789 (19) | 0.0280 (6) | |
C14 | 0.0830 (3) | −0.1565 (2) | −0.3165 (2) | 0.0333 (6) | |
C15 | 0.5761 (3) | −0.1406 (2) | −0.37003 (18) | 0.0271 (6) | |
C16 | 0.6643 (3) | −0.0680 (2) | −0.4304 (2) | 0.0331 (6) | |
H16 | 0.6989 | −0.0256 | −0.4069 | 0.040* | |
C17 | 0.7004 (3) | −0.0583 (2) | −0.5229 (2) | 0.0337 (6) | |
H17 | 0.7605 | −0.0096 | −0.5639 | 0.040* | |
C18 | 0.6479 (3) | −0.1210 (2) | −0.55703 (19) | 0.0299 (6) | |
C19 | 0.5597 (3) | −0.19174 (19) | −0.49131 (18) | 0.0250 (5) | |
C20 | 0.5006 (3) | −0.2583 (2) | −0.52032 (17) | 0.0248 (5) | |
C21 | 0.5305 (3) | −0.2531 (2) | −0.61455 (18) | 0.0292 (6) | |
C22 | 0.4655 (3) | −0.3189 (2) | −0.63757 (19) | 0.0326 (6) | |
H22 | 0.4809 | −0.3179 | −0.7004 | 0.039* | |
C23 | 0.3805 (3) | −0.3840 (2) | −0.57014 (18) | 0.0308 (6) | |
H23 | 0.3358 | −0.4279 | −0.5857 | 0.037* | |
C24 | 0.3596 (3) | −0.3856 (2) | −0.47696 (18) | 0.0264 (6) | |
C25 | 0.6768 (3) | −0.1183 (2) | −0.65205 (19) | 0.0333 (6) | |
H25 | 0.7367 | −0.0717 | −0.6969 | 0.040* | |
C26 | 0.6210 (3) | −0.1805 (2) | −0.67956 (19) | 0.0349 (6) | |
H26 | 0.6420 | −0.1761 | −0.7434 | 0.042* | |
C27 | 0.5275 (3) | −0.1559 (2) | −0.26719 (19) | 0.0301 (6) | |
C28 | 0.2712 (3) | −0.4568 (2) | −0.39516 (18) | 0.0276 (6) | |
N5 | 0.8010 (3) | −0.8300 (2) | −0.1744 (2) | 0.0640 (8) | |
H5A | 0.7521 | −0.8547 | −0.2026 | 0.077* | |
H5B | 0.7762 | −0.7619 | −0.1765 | 0.077* | |
N6 | 0.9723 (3) | −0.9812 (2) | −0.1703 (2) | 0.0604 (8) | |
H6A | 0.9292 | −0.9846 | −0.2154 | 0.073* | |
H6B | 1.0600 | −1.0209 | −0.1545 | 0.073* | |
C29 | 0.9287 (4) | −0.8931 (3) | −0.1516 (2) | 0.0517 (8) | |
C30 | 1.0219 (4) | −0.8639 (3) | −0.1027 (3) | 0.0615 (10) | |
H30A | 0.9621 | −0.8381 | −0.0545 | 0.092* | |
H30B | 1.0707 | −0.8069 | −0.1493 | 0.092* | |
H30C | 1.0939 | −0.9275 | −0.0721 | 0.092* | |
N7 | 0.1675 (2) | −0.59460 (18) | −0.54617 (16) | 0.0329 (5) | |
H7A | 0.1679 | −0.5739 | −0.4981 | 0.039* | |
H7B | 0.2252 | −0.5741 | −0.6008 | 0.039* | |
N8 | 0.0118 (2) | −0.70915 (18) | −0.45609 (16) | 0.0349 (5) | |
H8A | 0.0121 | −0.6954 | −0.4041 | 0.042* | |
H8B | −0.0380 | −0.7590 | −0.4501 | 0.042* | |
C31 | 0.0874 (3) | −0.6628 (2) | −0.53660 (19) | 0.0309 (6) | |
C32 | 0.0816 (3) | −0.6870 (2) | −0.6215 (2) | 0.0375 (7) | |
H32A | 0.1707 | −0.6759 | −0.6639 | 0.056* | |
H32B | −0.0011 | −0.6389 | −0.6551 | 0.056* | |
H32C | 0.0715 | −0.7621 | −0.6010 | 0.056* | |
O1W | 0.7167 (2) | −0.93913 (18) | −0.26699 (16) | 0.0517 (6) | |
H1WB | 0.6725 | −0.9894 | −0.2567 | 0.062* | |
H1WA | 0.7559 | −0.9119 | −0.3232 | 0.062* | |
O2W | 0.8697 (2) | −0.87175 (15) | −0.44941 (13) | 0.0374 (5) | |
H2WA | 0.9239 | −0.9339 | −0.4315 | 0.045* | |
H2WB | 0.8510 | −0.8574 | −0.5052 | 0.045* | |
O3W | 0.0311 (2) | −0.64852 (16) | −0.29789 (14) | 0.0433 (5) | |
H3WA | 0.0748 | −0.5962 | −0.3280 | 0.052* | |
H3WB | −0.0544 | −0.6172 | −0.2865 | 0.052* | |
O4W | 0.2349 (2) | −0.65284 (17) | −0.17187 (14) | 0.0455 (5) | |
H4WA | 0.1802 | −0.6675 | −0.2001 | 0.055* | |
H4WB | 0.2411 | −0.5878 | −0.2062 | 0.055* | |
O5W | 0.4446 (4) | −0.8419 (2) | −0.1000 (2) | 0.0860 (10) | |
H5WA | 0.3813 | −0.7841 | −0.1141 | 0.103* | |
H5WB | 0.4500 | −0.8624 | −0.0409 | 0.103* | |
O6W | 0.5485 (3) | −0.94350 (19) | 0.07739 (16) | 0.0579 (6) | |
H6WA | 0.5041 | −0.9299 | 0.1255 | 0.069* | |
H6WB | 0.5758 | −1.0060 | 0.0752 | 0.069* | |
O7W | 0.7721 (2) | −0.87078 (19) | 0.10478 (17) | 0.0560 (6) | |
H7WA | 0.7217 | −0.8988 | 0.0853 | 0.067* | |
H7WB | 0.7133 | −0.8399 | 0.1386 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0283 (2) | 0.0252 (2) | 0.0204 (2) | −0.00653 (17) | −0.00202 (16) | −0.00818 (17) |
O1 | 0.0312 (10) | 0.0301 (10) | 0.0291 (10) | −0.0049 (8) | −0.0017 (8) | −0.0083 (9) |
O2 | 0.0352 (11) | 0.0331 (11) | 0.0472 (12) | 0.0015 (9) | −0.0024 (9) | −0.0146 (9) |
O3 | 0.0336 (10) | 0.0295 (10) | 0.0315 (10) | −0.0048 (8) | −0.0076 (8) | −0.0084 (8) |
O4 | 0.0449 (13) | 0.0370 (12) | 0.0569 (14) | 0.0085 (10) | −0.0079 (10) | −0.0069 (10) |
O5 | 0.0441 (11) | 0.0353 (11) | 0.0285 (10) | −0.0152 (9) | −0.0045 (8) | −0.0127 (9) |
O6 | 0.0539 (13) | 0.0485 (12) | 0.0396 (11) | −0.0203 (10) | −0.0067 (9) | −0.0230 (10) |
O7 | 0.0396 (11) | 0.0334 (10) | 0.0273 (10) | −0.0131 (8) | −0.0031 (8) | −0.0134 (8) |
O8 | 0.0372 (11) | 0.0407 (11) | 0.0379 (11) | −0.0153 (9) | −0.0038 (8) | −0.0204 (9) |
N1 | 0.0286 (11) | 0.0243 (11) | 0.0247 (11) | −0.0051 (9) | −0.0060 (9) | −0.0113 (9) |
N2 | 0.0281 (12) | 0.0257 (11) | 0.0289 (12) | −0.0063 (9) | −0.0039 (9) | −0.0122 (10) |
N3 | 0.0272 (11) | 0.0215 (11) | 0.0269 (11) | −0.0028 (9) | −0.0064 (9) | −0.0095 (9) |
N4 | 0.0249 (11) | 0.0221 (11) | 0.0260 (11) | −0.0026 (9) | −0.0060 (9) | −0.0102 (9) |
C1 | 0.0333 (14) | 0.0247 (14) | 0.0293 (14) | −0.0079 (11) | −0.0086 (11) | −0.0112 (12) |
C2 | 0.0386 (16) | 0.0259 (14) | 0.0316 (15) | −0.0056 (12) | −0.0113 (12) | −0.0057 (12) |
C3 | 0.0480 (18) | 0.0325 (15) | 0.0273 (15) | −0.0142 (13) | −0.0128 (13) | −0.0031 (12) |
C4 | 0.0425 (16) | 0.0357 (16) | 0.0262 (14) | −0.0176 (13) | −0.0055 (12) | −0.0108 (12) |
C5 | 0.0333 (14) | 0.0277 (14) | 0.0236 (13) | −0.0123 (11) | −0.0040 (11) | −0.0108 (11) |
C6 | 0.0319 (14) | 0.0295 (14) | 0.0275 (14) | −0.0116 (11) | −0.0003 (11) | −0.0149 (12) |
C7 | 0.0378 (16) | 0.0438 (17) | 0.0356 (16) | −0.0180 (13) | 0.0044 (12) | −0.0233 (14) |
C8 | 0.0350 (16) | 0.0457 (18) | 0.0457 (18) | −0.0128 (14) | 0.0090 (13) | −0.0269 (15) |
C9 | 0.0321 (16) | 0.0356 (16) | 0.0527 (19) | −0.0052 (12) | 0.0012 (13) | −0.0225 (15) |
C10 | 0.0291 (15) | 0.0290 (15) | 0.0419 (16) | −0.0047 (12) | −0.0056 (12) | −0.0181 (13) |
C11 | 0.0515 (19) | 0.0471 (18) | 0.0229 (14) | −0.0254 (15) | −0.0001 (12) | −0.0110 (13) |
C12 | 0.0467 (18) | 0.0498 (19) | 0.0296 (15) | −0.0222 (15) | 0.0081 (13) | −0.0192 (14) |
C13 | 0.0270 (14) | 0.0278 (15) | 0.0337 (15) | −0.0054 (12) | −0.0062 (11) | −0.0145 (13) |
C14 | 0.0336 (16) | 0.0270 (15) | 0.0402 (16) | −0.0053 (12) | −0.0077 (13) | −0.0122 (13) |
C15 | 0.0262 (13) | 0.0239 (13) | 0.0318 (14) | −0.0022 (11) | −0.0074 (11) | −0.0105 (11) |
C16 | 0.0336 (15) | 0.0295 (15) | 0.0410 (17) | −0.0105 (12) | −0.0068 (12) | −0.0142 (13) |
C17 | 0.0310 (15) | 0.0300 (15) | 0.0383 (16) | −0.0107 (12) | −0.0022 (12) | −0.0086 (13) |
C18 | 0.0261 (14) | 0.0261 (14) | 0.0339 (15) | −0.0027 (11) | −0.0038 (11) | −0.0086 (12) |
C19 | 0.0235 (13) | 0.0212 (13) | 0.0280 (14) | −0.0010 (10) | −0.0044 (10) | −0.0079 (11) |
C20 | 0.0236 (13) | 0.0240 (13) | 0.0248 (13) | −0.0001 (10) | −0.0065 (10) | −0.0080 (11) |
C21 | 0.0291 (14) | 0.0303 (15) | 0.0259 (14) | 0.0001 (11) | −0.0052 (11) | −0.0106 (12) |
C22 | 0.0360 (15) | 0.0380 (16) | 0.0259 (14) | −0.0030 (12) | −0.0048 (12) | −0.0160 (13) |
C23 | 0.0354 (15) | 0.0321 (15) | 0.0299 (14) | −0.0059 (12) | −0.0057 (12) | −0.0160 (13) |
C24 | 0.0267 (13) | 0.0246 (13) | 0.0293 (14) | −0.0004 (11) | −0.0073 (11) | −0.0122 (11) |
C25 | 0.0307 (15) | 0.0349 (15) | 0.0281 (14) | −0.0090 (12) | 0.0030 (11) | −0.0066 (12) |
C26 | 0.0356 (15) | 0.0404 (17) | 0.0251 (14) | −0.0062 (13) | 0.0006 (12) | −0.0111 (13) |
C27 | 0.0347 (15) | 0.0261 (14) | 0.0327 (14) | −0.0051 (12) | −0.0106 (12) | −0.0115 (12) |
C28 | 0.0268 (14) | 0.0242 (14) | 0.0319 (15) | −0.0005 (11) | −0.0062 (11) | −0.0118 (12) |
N5 | 0.070 (2) | 0.0449 (17) | 0.083 (2) | 0.0005 (15) | −0.0239 (17) | −0.0293 (16) |
N6 | 0.0657 (19) | 0.0425 (16) | 0.081 (2) | 0.0048 (14) | −0.0284 (16) | −0.0308 (16) |
C29 | 0.055 (2) | 0.046 (2) | 0.054 (2) | −0.0131 (16) | −0.0062 (16) | −0.0152 (16) |
C30 | 0.073 (3) | 0.059 (2) | 0.059 (2) | −0.0178 (19) | −0.0177 (19) | −0.0208 (19) |
N7 | 0.0352 (13) | 0.0374 (13) | 0.0304 (12) | −0.0120 (11) | −0.0006 (10) | −0.0155 (11) |
N8 | 0.0334 (13) | 0.0360 (13) | 0.0359 (13) | −0.0091 (10) | −0.0043 (10) | −0.0123 (11) |
C31 | 0.0266 (14) | 0.0299 (15) | 0.0345 (15) | −0.0010 (12) | −0.0046 (12) | −0.0124 (12) |
C32 | 0.0351 (16) | 0.0399 (16) | 0.0428 (17) | −0.0070 (13) | −0.0063 (13) | −0.0200 (14) |
O1W | 0.0516 (13) | 0.0528 (14) | 0.0579 (14) | −0.0179 (11) | 0.0000 (11) | −0.0261 (12) |
O2W | 0.0433 (11) | 0.0324 (10) | 0.0354 (10) | −0.0074 (9) | −0.0120 (9) | −0.0081 (9) |
O3W | 0.0378 (11) | 0.0422 (12) | 0.0452 (12) | −0.0079 (9) | 0.0024 (9) | −0.0145 (10) |
O4W | 0.0535 (13) | 0.0419 (12) | 0.0386 (11) | −0.0154 (10) | −0.0028 (10) | −0.0096 (10) |
O5W | 0.135 (3) | 0.0618 (17) | 0.0708 (18) | 0.0146 (17) | −0.0524 (18) | −0.0365 (15) |
O6W | 0.0748 (16) | 0.0636 (15) | 0.0467 (13) | −0.0144 (12) | −0.0092 (11) | −0.0304 (12) |
O7W | 0.0481 (13) | 0.0637 (15) | 0.0654 (15) | −0.0037 (11) | −0.0068 (11) | −0.0373 (13) |
Mn1—N2 | 2.309 (2) | C17—H17 | 0.9500 |
Mn1—N4 | 2.312 (2) | C18—C19 | 1.412 (4) |
Mn1—N3 | 2.327 (2) | C18—C25 | 1.431 (4) |
Mn1—N1 | 2.329 (2) | C19—C20 | 1.439 (4) |
Mn1—O3 | 2.3630 (18) | C20—C21 | 1.407 (4) |
Mn1—O7 | 2.3863 (18) | C21—C22 | 1.407 (4) |
Mn1—O5 | 2.4382 (17) | C21—C26 | 1.438 (4) |
Mn1—O1 | 2.4645 (18) | C22—C23 | 1.361 (4) |
O1—C13 | 1.255 (3) | C22—H22 | 0.9500 |
O2—C13 | 1.251 (3) | C23—C24 | 1.410 (4) |
O3—C14 | 1.262 (3) | C23—H23 | 0.9500 |
O4—C14 | 1.237 (3) | C24—C28 | 1.517 (4) |
O5—C27 | 1.258 (3) | C25—C26 | 1.351 (4) |
O6—C27 | 1.253 (3) | C25—H25 | 0.9500 |
O7—C28 | 1.261 (3) | C26—H26 | 0.9500 |
O8—C28 | 1.250 (3) | N5—C29 | 1.332 (4) |
N1—C1 | 1.329 (3) | N5—H5A | 0.9000 |
N1—C5 | 1.348 (3) | N5—H5B | 0.9000 |
N2—C10 | 1.321 (3) | N6—C29 | 1.313 (4) |
N2—C6 | 1.345 (3) | N6—H6A | 0.9000 |
N3—C15 | 1.325 (3) | N6—H6B | 0.9000 |
N3—C19 | 1.351 (3) | C29—C30 | 1.493 (5) |
N4—C24 | 1.322 (3) | C30—H30A | 0.9800 |
N4—C20 | 1.345 (3) | C30—H30B | 0.9800 |
C1—C2 | 1.405 (4) | C30—H30C | 0.9800 |
C1—C13 | 1.514 (4) | N7—C31 | 1.310 (4) |
C2—C3 | 1.365 (4) | N7—H7A | 0.8999 |
C2—H2 | 0.9500 | N7—H7B | 0.9000 |
C3—C4 | 1.400 (4) | N8—C31 | 1.317 (4) |
C3—H3 | 0.9500 | N8—H8A | 0.9000 |
C4—C5 | 1.406 (4) | N8—H8B | 0.8999 |
C4—C11 | 1.436 (4) | C31—C32 | 1.495 (4) |
C5—C6 | 1.439 (4) | C32—H32A | 0.9800 |
C6—C7 | 1.405 (4) | C32—H32B | 0.9800 |
C7—C8 | 1.414 (4) | C32—H32C | 0.9800 |
C7—C12 | 1.430 (4) | O1W—H1WB | 0.8501 |
C8—C9 | 1.375 (4) | O1W—H1WA | 0.8499 |
C8—H8 | 0.9500 | O2W—H2WA | 0.8500 |
C9—C10 | 1.409 (4) | O2W—H2WB | 0.8499 |
C9—H9 | 0.9500 | O3W—H3WA | 0.8498 |
C10—C14 | 1.523 (4) | O3W—H3WB | 0.8501 |
C11—C12 | 1.354 (4) | O4W—H4WA | 0.8499 |
C11—H11 | 0.9500 | O4W—H4WB | 0.8500 |
C12—H12 | 0.9500 | O5W—H5WA | 0.8500 |
C15—C16 | 1.403 (4) | O5W—H5WB | 0.8499 |
C15—C27 | 1.514 (4) | O6W—H6WA | 0.8501 |
C16—C17 | 1.368 (4) | O6W—H6WB | 0.8499 |
C16—H16 | 0.9500 | O7W—H7WA | 0.8500 |
C17—C18 | 1.407 (4) | O7W—H7WB | 0.8501 |
N2—Mn1—N4 | 136.11 (7) | O4—C14—O3 | 126.9 (3) |
N2—Mn1—N3 | 132.09 (7) | O4—C14—C10 | 117.4 (2) |
N4—Mn1—N3 | 69.49 (7) | O3—C14—C10 | 115.6 (2) |
N2—Mn1—N1 | 69.13 (7) | N3—C15—C16 | 122.0 (2) |
N4—Mn1—N1 | 130.55 (7) | N3—C15—C27 | 113.8 (2) |
N3—Mn1—N1 | 131.49 (7) | C16—C15—C27 | 124.1 (2) |
N2—Mn1—O3 | 67.82 (7) | C17—C16—C15 | 119.9 (2) |
N4—Mn1—O3 | 80.79 (7) | C17—C16—H16 | 120.0 |
N3—Mn1—O3 | 83.18 (7) | C15—C16—H16 | 120.0 |
N1—Mn1—O3 | 136.69 (7) | C16—C17—C18 | 119.6 (3) |
N2—Mn1—O7 | 83.15 (7) | C16—C17—H17 | 120.2 |
N4—Mn1—O7 | 67.47 (7) | C18—C17—H17 | 120.2 |
N3—Mn1—O7 | 136.91 (7) | C17—C18—C19 | 116.6 (2) |
N1—Mn1—O7 | 78.60 (7) | C17—C18—C25 | 125.2 (3) |
O3—Mn1—O7 | 91.77 (6) | C19—C18—C25 | 118.2 (2) |
N2—Mn1—O5 | 75.67 (7) | N3—C19—C18 | 123.4 (2) |
N4—Mn1—O5 | 135.37 (7) | N3—C19—C20 | 116.3 (2) |
N3—Mn1—O5 | 66.19 (7) | C18—C19—C20 | 120.3 (2) |
N1—Mn1—O5 | 85.00 (7) | N4—C20—C21 | 123.3 (2) |
O3—Mn1—O5 | 88.98 (6) | N4—C20—C19 | 116.7 (2) |
O7—Mn1—O5 | 156.79 (6) | C21—C20—C19 | 120.0 (2) |
N2—Mn1—O1 | 135.12 (7) | C22—C21—C20 | 116.3 (3) |
N4—Mn1—O1 | 79.20 (6) | C22—C21—C26 | 125.4 (2) |
N3—Mn1—O1 | 79.36 (7) | C20—C21—C26 | 118.3 (2) |
N1—Mn1—O1 | 66.09 (6) | C23—C22—C21 | 120.2 (2) |
O3—Mn1—O1 | 157.04 (6) | C23—C22—H22 | 119.9 |
O7—Mn1—O1 | 90.89 (6) | C21—C22—H22 | 119.9 |
O5—Mn1—O1 | 97.40 (6) | C22—C23—C24 | 119.4 (2) |
C13—O1—Mn1 | 119.48 (16) | C22—C23—H23 | 120.3 |
C14—O3—Mn1 | 120.52 (16) | C24—C23—H23 | 120.3 |
C27—O5—Mn1 | 120.15 (16) | N4—C24—C23 | 121.7 (3) |
C28—O7—Mn1 | 120.22 (17) | N4—C24—C28 | 114.0 (2) |
C1—N1—C5 | 118.4 (2) | C23—C24—C28 | 124.3 (2) |
C1—N1—Mn1 | 122.99 (17) | C26—C25—C18 | 121.6 (3) |
C5—N1—Mn1 | 118.63 (16) | C26—C25—H25 | 119.2 |
C10—N2—C6 | 119.0 (2) | C18—C25—H25 | 119.2 |
C10—N2—Mn1 | 121.43 (18) | C25—C26—C21 | 121.6 (2) |
C6—N2—Mn1 | 119.54 (16) | C25—C26—H26 | 119.2 |
C15—N3—C19 | 118.5 (2) | C21—C26—H26 | 119.2 |
C15—N3—Mn1 | 123.05 (17) | O6—C27—O5 | 126.0 (3) |
C19—N3—Mn1 | 118.41 (16) | O6—C27—C15 | 118.0 (3) |
C24—N4—C20 | 119.1 (2) | O5—C27—C15 | 116.0 (2) |
C24—N4—Mn1 | 121.88 (17) | O8—C28—O7 | 126.0 (3) |
C20—N4—Mn1 | 119.00 (15) | O8—C28—C24 | 118.0 (2) |
N1—C1—C2 | 122.1 (2) | O7—C28—C24 | 116.0 (2) |
N1—C1—C13 | 114.2 (2) | C29—N5—H5A | 113.1 |
C2—C1—C13 | 123.7 (2) | C29—N5—H5B | 123.4 |
C3—C2—C1 | 119.3 (3) | H5A—N5—H5B | 121.6 |
C3—C2—H2 | 120.4 | C29—N6—H6A | 116.3 |
C1—C2—H2 | 120.4 | C29—N6—H6B | 117.8 |
C2—C3—C4 | 120.1 (3) | H6A—N6—H6B | 122.1 |
C2—C3—H3 | 120.0 | N6—C29—N5 | 120.7 (3) |
C4—C3—H3 | 120.0 | N6—C29—C30 | 119.8 (3) |
C3—C4—C5 | 116.7 (3) | N5—C29—C30 | 119.5 (3) |
C3—C4—C11 | 125.5 (3) | C29—C30—H30A | 109.5 |
C5—C4—C11 | 117.9 (3) | C29—C30—H30B | 109.5 |
N1—C5—C4 | 123.4 (2) | H30A—C30—H30B | 109.5 |
N1—C5—C6 | 116.4 (2) | C29—C30—H30C | 109.5 |
C4—C5—C6 | 120.2 (2) | H30A—C30—H30C | 109.5 |
N2—C6—C7 | 123.6 (2) | H30B—C30—H30C | 109.5 |
N2—C6—C5 | 116.1 (2) | C31—N7—H7A | 120.3 |
C7—C6—C5 | 120.2 (2) | C31—N7—H7B | 116.6 |
C6—C7—C8 | 116.4 (3) | H7A—N7—H7B | 122.9 |
C6—C7—C12 | 118.5 (3) | C31—N8—H8A | 121.6 |
C8—C7—C12 | 125.0 (3) | C31—N8—H8B | 121.0 |
C9—C8—C7 | 119.6 (3) | H8A—N8—H8B | 117.3 |
C9—C8—H8 | 120.2 | N7—C31—N8 | 122.6 (2) |
C7—C8—H8 | 120.2 | N7—C31—C32 | 117.9 (2) |
C8—C9—C10 | 119.3 (3) | N8—C31—C32 | 119.6 (2) |
C8—C9—H9 | 120.4 | C31—C32—H32A | 109.5 |
C10—C9—H9 | 120.4 | C31—C32—H32B | 109.5 |
N2—C10—C9 | 122.0 (3) | H32A—C32—H32B | 109.5 |
N2—C10—C14 | 113.9 (2) | C31—C32—H32C | 109.5 |
C9—C10—C14 | 124.1 (2) | H32A—C32—H32C | 109.5 |
C12—C11—C4 | 122.0 (3) | H32B—C32—H32C | 109.5 |
C12—C11—H11 | 119.0 | H1WB—O1W—H1WA | 115.9 |
C4—C11—H11 | 119.0 | H2WA—O2W—H2WB | 107.1 |
C11—C12—C7 | 121.1 (3) | H3WA—O3W—H3WB | 103.0 |
C11—C12—H12 | 119.4 | H4WA—O4W—H4WB | 103.6 |
C7—C12—H12 | 119.4 | H5WA—O5W—H5WB | 105.4 |
O2—C13—O1 | 126.1 (2) | H6WA—O6W—H6WB | 125.3 |
O2—C13—C1 | 117.7 (2) | H7WA—O7W—H7WB | 105.6 |
O1—C13—C1 | 116.2 (2) | ||
N2—Mn1—O1—C13 | 13.5 (2) | C3—C4—C5—N1 | −2.4 (4) |
N4—Mn1—O1—C13 | −134.56 (18) | C11—C4—C5—N1 | 176.4 (2) |
N3—Mn1—O1—C13 | 154.53 (18) | C3—C4—C5—C6 | 177.5 (2) |
N1—Mn1—O1—C13 | 9.39 (17) | C11—C4—C5—C6 | −3.7 (4) |
O3—Mn1—O1—C13 | −164.36 (18) | C10—N2—C6—C7 | −1.4 (4) |
O7—Mn1—O1—C13 | −67.71 (18) | Mn1—N2—C6—C7 | 175.47 (19) |
O5—Mn1—O1—C13 | 90.55 (18) | C10—N2—C6—C5 | 177.9 (2) |
N2—Mn1—O3—C14 | 7.74 (18) | Mn1—N2—C6—C5 | −5.2 (3) |
N4—Mn1—O3—C14 | 156.4 (2) | N1—C5—C6—N2 | 3.0 (3) |
N3—Mn1—O3—C14 | −133.32 (19) | C4—C5—C6—N2 | −176.8 (2) |
N1—Mn1—O3—C14 | 14.4 (2) | N1—C5—C6—C7 | −177.6 (2) |
O7—Mn1—O3—C14 | 89.61 (19) | C4—C5—C6—C7 | 2.6 (4) |
O5—Mn1—O3—C14 | −67.18 (19) | N2—C6—C7—C8 | 1.9 (4) |
O1—Mn1—O3—C14 | −173.92 (18) | C5—C6—C7—C8 | −177.4 (2) |
N2—Mn1—O5—C27 | −158.4 (2) | N2—C6—C7—C12 | 179.9 (2) |
N4—Mn1—O5—C27 | −15.3 (2) | C5—C6—C7—C12 | 0.5 (4) |
N3—Mn1—O5—C27 | −8.08 (18) | C6—C7—C8—C9 | −0.3 (4) |
N1—Mn1—O5—C27 | 131.87 (19) | C12—C7—C8—C9 | −178.1 (3) |
O3—Mn1—O5—C27 | −91.07 (19) | C7—C8—C9—C10 | −1.6 (4) |
O7—Mn1—O5—C27 | 176.82 (18) | C6—N2—C10—C9 | −0.7 (4) |
O1—Mn1—O5—C27 | 66.80 (19) | Mn1—N2—C10—C9 | −177.49 (19) |
N2—Mn1—O7—C28 | 140.83 (18) | C6—N2—C10—C14 | 177.9 (2) |
N4—Mn1—O7—C28 | −5.86 (17) | Mn1—N2—C10—C14 | 1.1 (3) |
N3—Mn1—O7—C28 | −8.5 (2) | C8—C9—C10—N2 | 2.2 (4) |
N1—Mn1—O7—C28 | −149.16 (18) | C8—C9—C10—C14 | −176.3 (3) |
O3—Mn1—O7—C28 | 73.41 (18) | C3—C4—C11—C12 | −179.4 (3) |
O5—Mn1—O7—C28 | 164.95 (17) | C5—C4—C11—C12 | 1.9 (4) |
O1—Mn1—O7—C28 | −83.78 (18) | C4—C11—C12—C7 | 1.2 (4) |
N2—Mn1—N1—C1 | 176.7 (2) | C6—C7—C12—C11 | −2.4 (4) |
N4—Mn1—N1—C1 | 43.1 (2) | C8—C7—C12—C11 | 175.3 (3) |
N3—Mn1—N1—C1 | −55.0 (2) | Mn1—O1—C13—O2 | 168.8 (2) |
O3—Mn1—N1—C1 | 170.03 (16) | Mn1—O1—C13—C1 | −11.0 (3) |
O7—Mn1—N1—C1 | 89.71 (19) | N1—C1—C13—O2 | −174.7 (2) |
O5—Mn1—N1—C1 | −106.80 (19) | C2—C1—C13—O2 | 6.8 (4) |
O1—Mn1—N1—C1 | −6.42 (17) | N1—C1—C13—O1 | 5.1 (3) |
N2—Mn1—N1—C5 | −2.20 (16) | C2—C1—C13—O1 | −173.4 (2) |
N4—Mn1—N1—C5 | −135.73 (16) | Mn1—O3—C14—O4 | 170.2 (2) |
N3—Mn1—N1—C5 | 126.16 (17) | Mn1—O3—C14—C10 | −9.9 (3) |
O3—Mn1—N1—C5 | −8.8 (2) | N2—C10—C14—O4 | −174.3 (2) |
O7—Mn1—N1—C5 | −89.14 (17) | C9—C10—C14—O4 | 4.2 (4) |
O5—Mn1—N1—C5 | 74.35 (17) | N2—C10—C14—O3 | 5.8 (3) |
O1—Mn1—N1—C5 | 174.73 (19) | C9—C10—C14—O3 | −175.7 (2) |
N4—Mn1—N2—C10 | −51.9 (2) | C19—N3—C15—C16 | −0.2 (4) |
N3—Mn1—N2—C10 | 53.1 (2) | Mn1—N3—C15—C16 | 178.83 (18) |
N1—Mn1—N2—C10 | −179.3 (2) | C19—N3—C15—C27 | 178.6 (2) |
O3—Mn1—N2—C10 | −4.16 (18) | Mn1—N3—C15—C27 | −2.4 (3) |
O7—Mn1—N2—C10 | −98.89 (19) | N3—C15—C16—C17 | −0.1 (4) |
O5—Mn1—N2—C10 | 90.68 (19) | C27—C15—C16—C17 | −178.8 (2) |
O1—Mn1—N2—C10 | 176.76 (17) | C15—C16—C17—C18 | 0.4 (4) |
N4—Mn1—N2—C6 | 131.34 (17) | C16—C17—C18—C19 | −0.3 (4) |
N3—Mn1—N2—C6 | −123.72 (17) | C16—C17—C18—C25 | 179.7 (3) |
N1—Mn1—N2—C6 | 3.94 (17) | C15—N3—C19—C18 | 0.3 (4) |
O3—Mn1—N2—C6 | 179.04 (19) | Mn1—N3—C19—C18 | −178.78 (18) |
O7—Mn1—N2—C6 | 84.31 (18) | C15—N3—C19—C20 | −179.4 (2) |
O5—Mn1—N2—C6 | −86.12 (18) | Mn1—N3—C19—C20 | 1.6 (3) |
O1—Mn1—N2—C6 | 0.0 (2) | C17—C18—C19—N3 | −0.1 (4) |
N2—Mn1—N3—C15 | 45.3 (2) | C25—C18—C19—N3 | 180.0 (2) |
N4—Mn1—N3—C15 | 179.7 (2) | C17—C18—C19—C20 | 179.6 (2) |
N1—Mn1—N3—C15 | −53.8 (2) | C25—C18—C19—C20 | −0.4 (4) |
O3—Mn1—N3—C15 | 96.98 (19) | C24—N4—C20—C21 | −1.5 (4) |
O7—Mn1—N3—C15 | −177.74 (16) | Mn1—N4—C20—C21 | 179.14 (18) |
O5—Mn1—N3—C15 | 5.08 (18) | C24—N4—C20—C19 | 178.9 (2) |
O1—Mn1—N3—C15 | −97.99 (19) | Mn1—N4—C20—C19 | −0.5 (3) |
N2—Mn1—N3—C19 | −135.64 (16) | N3—C19—C20—N4 | −0.7 (3) |
N4—Mn1—N3—C19 | −1.30 (16) | C18—C19—C20—N4 | 179.6 (2) |
N1—Mn1—N3—C19 | 125.27 (17) | N3—C19—C20—C21 | 179.7 (2) |
O3—Mn1—N3—C19 | −83.99 (17) | C18—C19—C20—C21 | 0.0 (4) |
O7—Mn1—N3—C19 | 1.3 (2) | N4—C20—C21—C22 | 2.0 (4) |
O5—Mn1—N3—C19 | −175.89 (19) | C19—C20—C21—C22 | −178.4 (2) |
O1—Mn1—N3—C19 | 81.04 (17) | N4—C20—C21—C26 | −179.4 (2) |
N2—Mn1—N4—C24 | −48.4 (2) | C19—C20—C21—C26 | 0.2 (4) |
N3—Mn1—N4—C24 | −178.4 (2) | C20—C21—C22—C23 | −0.9 (4) |
N1—Mn1—N4—C24 | 53.9 (2) | C26—C21—C22—C23 | −179.4 (2) |
O3—Mn1—N4—C24 | −92.32 (19) | C21—C22—C23—C24 | −0.6 (4) |
O7—Mn1—N4—C24 | 3.49 (17) | C20—N4—C24—C23 | −0.1 (4) |
O5—Mn1—N4—C24 | −171.37 (16) | Mn1—N4—C24—C23 | 179.22 (17) |
O1—Mn1—N4—C24 | 99.01 (19) | C20—N4—C24—C28 | 179.3 (2) |
N2—Mn1—N4—C20 | 130.95 (17) | Mn1—N4—C24—C28 | −1.4 (3) |
N3—Mn1—N4—C20 | 0.90 (16) | C22—C23—C24—N4 | 1.2 (4) |
N1—Mn1—N4—C20 | −126.74 (17) | C22—C23—C24—C28 | −178.2 (2) |
O3—Mn1—N4—C20 | 87.01 (17) | C17—C18—C25—C26 | −179.3 (3) |
O7—Mn1—N4—C20 | −177.19 (19) | C19—C18—C25—C26 | 0.6 (4) |
O5—Mn1—N4—C20 | 8.0 (2) | C18—C25—C26—C21 | −0.5 (4) |
O1—Mn1—N4—C20 | −81.66 (17) | C22—C21—C26—C25 | 178.5 (3) |
C5—N1—C1—C2 | 1.1 (4) | C20—C21—C26—C25 | 0.1 (4) |
Mn1—N1—C1—C2 | −177.75 (18) | Mn1—O5—C27—O6 | −170.0 (2) |
C5—N1—C1—C13 | −177.5 (2) | Mn1—O5—C27—C15 | 9.8 (3) |
Mn1—N1—C1—C13 | 3.7 (3) | N3—C15—C27—O6 | 174.7 (2) |
N1—C1—C2—C3 | −2.5 (4) | C16—C15—C27—O6 | −6.5 (4) |
C13—C1—C2—C3 | 175.9 (2) | N3—C15—C27—O5 | −5.0 (3) |
C1—C2—C3—C4 | 1.4 (4) | C16—C15—C27—O5 | 173.7 (2) |
C2—C3—C4—C5 | 0.9 (4) | Mn1—O7—C28—O8 | −172.32 (19) |
C2—C3—C4—C11 | −177.8 (3) | Mn1—O7—C28—C24 | 7.3 (3) |
C1—N1—C5—C4 | 1.4 (4) | N4—C24—C28—O8 | 175.7 (2) |
Mn1—N1—C5—C4 | −179.72 (18) | C23—C24—C28—O8 | −4.9 (4) |
C1—N1—C5—C6 | −178.4 (2) | N4—C24—C28—O7 | −3.9 (3) |
Mn1—N1—C5—C6 | 0.5 (3) | C23—C24—C28—O7 | 175.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···O1W | 0.90 | 1.93 | 2.792 (4) | 159 |
N5—H5B···O2 | 0.90 | 1.93 | 2.797 (3) | 161 |
N6—H6A···O1W | 0.90 | 2.19 | 2.938 (4) | 140 |
N6—H6B···O7Wi | 0.90 | 1.94 | 2.830 (3) | 169 |
N7—H7A···O8 | 0.90 | 1.96 | 2.840 (3) | 167 |
N7—H7B···O1ii | 0.90 | 1.93 | 2.812 (3) | 168 |
N8—H8A···O3W | 0.90 | 2.05 | 2.941 (3) | 172 |
N8—H8B···O2Wiii | 0.90 | 1.98 | 2.871 (3) | 173 |
O1W—H1WB···O6iv | 0.85 | 1.93 | 2.780 (3) | 178 |
O1W—H1WA···O2W | 0.85 | 1.98 | 2.826 (3) | 171 |
O2W—H2WA···O4v | 0.85 | 1.92 | 2.709 (3) | 154 |
O2W—H2WB···O3ii | 0.85 | 1.90 | 2.753 (3) | 177 |
O3W—H3WA···O8 | 0.85 | 1.87 | 2.687 (3) | 161 |
O3W—H3WB···O2iii | 0.85 | 1.94 | 2.741 (3) | 156 |
O4W—H4WA···O3W | 0.85 | 2.18 | 2.996 (3) | 161 |
O4W—H4WB···O7 | 0.85 | 1.98 | 2.808 (3) | 164 |
O5W—H5WA···O4W | 0.85 | 1.99 | 2.828 (3) | 168 |
O5W—H5WB···O6W | 0.85 | 1.99 | 2.783 (3) | 154 |
O6W—H6WA···O6vi | 0.85 | 1.89 | 2.737 (3) | 174 |
O6W—H6WB···O5Wvii | 0.85 | 2.03 | 2.826 (4) | 155 |
O7W—H7WA···O6W | 0.85 | 1.96 | 2.760 (3) | 157 |
O7W—H7WB···O5vi | 0.85 | 2.02 | 2.865 (3) | 173 |
Symmetry codes: (i) −x+2, −y−2, −z; (ii) −x+1, −y−1, −z−1; (iii) x−1, y, z; (iv) x, y−1, z; (v) x+1, y−1, z; (vi) −x+1, −y−1, −z; (vii) −x+1, −y−2, −z. |
Experimental details
Crystal data | |
Chemical formula | (C2H7N2)2[Mn(C14H6N2O4)2]·7H2O |
Mr | 831.66 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 9.6330 (6), 13.8174 (7), 15.4828 (8) |
α, β, γ (°) | 66.151 (5), 78.949 (5), 75.397 (5) |
V (Å3) | 1814.56 (19) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 3.69 |
Crystal size (mm) | 0.29 × 0.26 × 0.16 |
Data collection | |
Diffractometer | Agilent Gemini S Ultra CCD |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.395, 0.554 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10581, 5310, 4336 |
Rint | 0.024 |
θmax (°) | 60.0 |
(sin θ/λ)max (Å−1) | 0.562 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.102, 0.95 |
No. of reflections | 5310 |
No. of parameters | 507 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.49, −0.38 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···O1W | 0.90 | 1.93 | 2.792 (4) | 158.9 |
N5—H5B···O2 | 0.90 | 1.93 | 2.797 (3) | 161.4 |
N6—H6A···O1W | 0.90 | 2.19 | 2.938 (4) | 140.1 |
N6—H6B···O7Wi | 0.90 | 1.94 | 2.830 (3) | 168.5 |
N7—H7A···O8 | 0.90 | 1.96 | 2.840 (3) | 166.8 |
N7—H7B···O1ii | 0.90 | 1.93 | 2.812 (3) | 167.5 |
N8—H8A···O3W | 0.90 | 2.05 | 2.941 (3) | 171.8 |
N8—H8B···O2Wiii | 0.90 | 1.98 | 2.871 (3) | 173.0 |
O1W—H1WB···O6iv | 0.85 | 1.93 | 2.780 (3) | 177.6 |
O1W—H1WA···O2W | 0.85 | 1.98 | 2.826 (3) | 170.5 |
O2W—H2WA···O4v | 0.85 | 1.92 | 2.709 (3) | 153.5 |
O2W—H2WB···O3ii | 0.85 | 1.90 | 2.753 (3) | 177.2 |
O3W—H3WA···O8 | 0.85 | 1.87 | 2.687 (3) | 161.3 |
O3W—H3WB···O2iii | 0.85 | 1.94 | 2.741 (3) | 156.0 |
O4W—H4WA···O3W | 0.85 | 2.18 | 2.996 (3) | 161.3 |
O4W—H4WB···O7 | 0.85 | 1.98 | 2.808 (3) | 163.6 |
O5W—H5WA···O4W | 0.85 | 1.99 | 2.828 (3) | 168.3 |
O5W—H5WB···O6W | 0.85 | 1.99 | 2.783 (3) | 153.8 |
O6W—H6WA···O6vi | 0.85 | 1.89 | 2.737 (3) | 174.1 |
O6W—H6WB···O5Wvii | 0.85 | 2.03 | 2.826 (4) | 155.3 |
O7W—H7WA···O6W | 0.85 | 1.96 | 2.760 (3) | 156.5 |
O7W—H7WB···O5vi | 0.85 | 2.02 | 2.865 (3) | 172.8 |
Symmetry codes: (i) −x+2, −y−2, −z; (ii) −x+1, −y−1, −z−1; (iii) x−1, y, z; (iv) x, y−1, z; (v) x+1, y−1, z; (vi) −x+1, −y−1, −z; (vii) −x+1, −y−2, −z. |
Acknowledgements
The authors acknowledge Guang Dong Ocean University for supporting this work.
References
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1,10-Phenanthroline and its substituted derivatives have versatile chelating and bridging capability(Kaes et al., 2000; Albores & Rentschler, 2008) which have played an important role in the development of coordination chemistry while the oxime, similar to the cyanide, can link two magnetic moment carriers with the shortest pairwise exchange pathway (Sreerama & Pal, 2004). Preliminary study on the coordination chemistry of 1,10-phenanthroline-2,9-dicarboxylate (H2phenda) found that it chelates the metal ions such as Ca(II), Cu(II), Th(III), Eu(III) and Tb(III) as a tridentate or tetradentate ligand by the phenanthroline and one or both of the oxygen atoms on the carboxylate groups (Dean et al., 2008; Gephart et al., 2008; Moghimi et al., 2005; Fan et al., 2008). We report here the crystal structure of the title compound, (I).
The title compound is ionic and contains discrete 1,10-phenanthroline- 2,9-dicarboxylate manganese(II) anions, ethanamidinium cations and water molecules (Fig. 1). The Mn atom is coordinated by four N atoms and four O atoms from two 1,10-phenanthroline-2,9-dicarboxylate ligands in a distorted dodecahedron geometry.
In the crystal structure, intermolecular π-π interactions (Figure 2) between the neighboring aromatic rings of phenda ligands link the molecules into an infinite layer. The centroid to centroid distance between pyridine rings is 3.553 (2) Å. The crystal packing is further stabilized by N—H···O and O—H···O hydrogen bonds (Table 1 and Figure 3), which link the layers into a three dimensional framework (Figure 4).