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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m161.
Published online 2007 December 12. doi:  10.1107/S1600536807065269
PMCID: PMC2915099

Tetra­kis(μ-phenoxy­acetato-κ2 O:O′)bis­[(1,10-phenanthroline-κ2 N,N′)manganese(II)] methanol hemisolvate

Abstract

The title complex, [Mn2(C8H7O3)4(C12H8N2)2]·0.5CH3OH, is a carboxyl­ate-bridged dinuclear MnII complex with four phenoxy­acetate ions and two 1,10-phenanthroline mol­ecules as ligands. Each of the four phenoxy­acetate anions bridges the pair of Mn atoms. The asymmetric unit is completed by a half-occupancy methanol solvent mol­ecule. Face-to-face π–π stacking inter­actions between the aromatic rings of 1,10-phenanthroline molecules belonging to adjacent Mn2 complexes, with an inter­planar separation of circa 3.4 Å, and weak C—H(...)O hydrogen bonds connect the dinuclear units into a three-dimensional supra­molecular framework.

Related literature

For related literature, see: Jiang et al. (2005 [triangle], 2006 [triangle]); Sessoli et al. (1993 [triangle]); Yaghi et al. (1997 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m161-scheme1.jpg

Experimental

Crystal data

  • [Mn2(C8H7O3)4(C12H8N2)2]·0.5CH4O
  • M r = 1090.86
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m161-efi1.jpg
  • a = 12.4627 (10) Å
  • b = 12.8334 (10) Å
  • c = 17.1377 (13) Å
  • α = 77.421 (1)°
  • β = 87.635 (1)°
  • γ = 84.629 (1)°
  • V = 2662.8 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.54 mm−1
  • T = 193 (2) K
  • 0.30 × 0.24 × 0.22 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.848, T max = 0.879
  • 14596 measured reflections
  • 10273 independent reflections
  • 6679 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.149
  • S = 1.08
  • 10273 reflections
  • 675 parameters
  • H-atom parameters constrained
  • Δρmax = 0.97 e Å−3
  • Δρmin = −0.53 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 2000 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065269/bh2151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065269/bh2151Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Natural Science Foundation of JiangSu Education Department (grant No. 06KJD150154).

supplementary crystallographic information

Comment

The rational design, synthesis and characterization of novel supramolecular frameworks are currently of great interest. One of the greatest challenges in this area is the construction of porous materials from metal ions and organic ligands as building blocks (Yaghi et al., 1997). As part of our search for new porous metal-organic frameworks, we are studying complexes of transition metals with phenoxyacetate ligands (Jiang et al., 2005, 2006). Here, the title compound, (I), a novel dinuclear MnII complex with 1,10-phenanthroline as co-ligands, is reported.

Complex (I) exists as a dinuclear unit, with four bidentate phenoxyacetate anions bridging the pair of MnII atoms (Fig. 1). Two N atoms from 1,10-phenanthroline molecules bind to the MnII atoms, and both MnII atoms thus possess a distorted octahedral coordination geometry. The asymmetric unit is completed by 1/2 methanol solvate. The Mn—O distances are in the range 2.087 (2) to 2.351 (3) Å, and the average distance for Mn—N bonds is 2.31 Å. The planes of two coordinated phenanthroline molecules are set approximately perpendicular to each other.

Interestingly, The Mn2 units further link to each other into a microporous framework (Fig. 2) by π-stacking from the plane of 1,10-phenanthroline of symmetry-related molecules and C—H···O hydrogen bond interactions between alternating molecules. These supramolecular interactions are illustrated in Fig. 3. The C—H···O hydrogen bonds that exist in the peripheral ligands of adjacent Mn2 complexes are formed via the H donor atoms from phenyl group and acceptor O atoms of OCH2 groups of phenoxyacetate ligands. It is noteworthy that the contacts are almost linear (C—H···O: 174.9°). The structural significance is that the dipole-monopole and dipole-dipole contributions to electrostatic energy are maximum at 180° and zero at 90°. Therefore, this interaction may be considered as an efficient C—H···O hydrogen bond.

The overall three-dimensional supramolecular structure is also stabilized by significant offset face-to-face π···π stacking interactions between the aromatic rings of 1,10-phenanthroline molecules belonging to adjacent Mn2 complexes, with an interplanar separation of ca 3.4 Å and θ = 21.9° (Fig. 3).

Experimental

[Mn3O(O2CCH2OPh)6(pyridine)2(H2O)] was synthesized according to the literature method of Sessoli et al., (1993). To a solution of [Mn3O(O2CCH2OPh)6(pyridine)2(H2O)] (0.15 mmol 0.18 g) in MeCN (8 ml) and CH3OH (2 ml), powdered 1,10-phenanthroline (0.15 mmol 0.030 g) was added. The resulting solution was stirred for 0.5 h., filtered and layered with two volumes of Et2O. After two weeks, light brown crystals of (I) were collected by filtration, washed with Et2O, and dried in vacuo. The yield was approximately 20%.

Refinement

Carbon-bound H atoms were positioned geometrically, with C—H = 0.97 Å for methylene groups, 0.93 Å for aromatic groups, and 0.96 Å for the methyl groups of MeOH. They were refined using a riding model, with Uiso(H) = 1.2Ueq(carrier C) for the complex and Uiso(H) = 1.5Ueq(C57) for the MeOH molecule. The hydroxyl H atom H13a was positioned geometrically and freely refined. Occupancy for the methanol molecule was refined in preliminary cycles and fixed to 1/2 for final refinement. Finally, geometry for phenyl ring C1···C6 was constrained by fitting the six C atoms to a regular hexagon with C?C bond lengths of 1.39 Å.

Figures

Fig. 1.
The structure of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted.
Fig. 2.
View of the microporous network of (I) along [001]. The guest CH3OH molecules and H atoms are omitted for clarity.
Fig. 3.
The π···π interactions and C—H···O hydrogen interactions in (I) are shown (dashed lines). Cg1 is the centroid of the interacting aromatic ring of 1,10-phenanthroline molecule in the ...

Crystal data

[Mn2(C8H7O3)4(C12H8N2)2]·0.5CH4OZ = 2
Mr = 1090.86F000 = 1126.0
Triclinic, P1Dx = 1.363 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 12.4627 (10) ÅCell parameters from 14596 reflections
b = 12.8334 (10) Åθ = 2.4–28.1º
c = 17.1377 (13) ŵ = 0.54 mm1
α = 77.421 (1)ºT = 193 (2) K
β = 87.635 (1)ºPrism, light brown
γ = 84.629 (1)º0.30 × 0.24 × 0.22 mm
V = 2662.8 (4) Å3

Data collection

Bruker SMART APEX CCD area detector diffractometer10273 independent reflections
Radiation source: fine-focus sealed tube6679 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.030
T = 193(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −12→15
Tmin = 0.848, Tmax = 0.879k = −15→15
14596 measured reflectionsl = −21→20

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.149  w = 1/[σ2(Fo2) + (0.0726P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
10273 reflectionsΔρmax = 0.97 e Å3
675 parametersΔρmin = −0.53 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
C1−0.14992 (18)0.29242 (18)0.19427 (14)0.0413 (8)
C2−0.2086 (2)0.29890 (17)0.12587 (12)0.0528 (10)
H2−0.19870.35320.08110.063*
C3−0.28204 (19)0.2243 (2)0.12443 (12)0.0400 (8)
H3−0.32130.22860.07870.048*
C4−0.29687 (19)0.14321 (18)0.19139 (14)0.0448 (9)
H4−0.34600.09330.19040.054*
C5−0.2382 (2)0.13673 (19)0.25979 (12)0.0525 (11)
H5−0.24810.08250.30460.063*
C6−0.1647 (2)0.2113 (2)0.26123 (12)0.0533 (11)
H6−0.12550.20700.30700.064*
C7−0.0082 (3)0.3575 (3)0.2531 (2)0.0420 (9)
H7A0.03710.29110.25580.050*
H7B−0.04860.35210.30320.050*
C80.0627 (3)0.4501 (3)0.24232 (19)0.0309 (7)
C90.5655 (3)0.5993 (3)0.1346 (2)0.0354 (7)
C100.6748 (3)0.5765 (3)0.1533 (2)0.0393 (8)
H100.70770.50770.15600.047*
C110.7337 (3)0.6559 (3)0.1676 (2)0.0408 (8)
H110.80640.64020.17920.049*
C120.6876 (3)0.7566 (3)0.1652 (2)0.0445 (9)
H120.72880.80950.17410.053*
C130.5785 (3)0.7801 (3)0.1493 (2)0.0399 (8)
H130.54580.84830.14900.048*
C140.5185 (3)0.7011 (3)0.1337 (2)0.0442 (9)
H140.44570.71720.12260.053*
C150.4190 (3)0.5449 (3)0.0745 (2)0.0389 (8)
H15A0.40780.48730.04800.047*
H15B0.42830.60860.03330.047*
C160.3174 (3)0.5660 (3)0.1243 (2)0.0310 (7)
C170.3770 (3)1.0392 (3)0.1738 (2)0.0393 (8)
C180.3870 (3)1.0841 (3)0.2409 (2)0.0452 (9)
H180.37411.04490.29230.054*
C190.4157 (3)1.1856 (3)0.2287 (2)0.0438 (9)
H190.41901.21660.27270.053*
C200.4399 (3)1.2444 (3)0.1549 (2)0.0480 (10)
H200.46201.31300.14850.058*
C210.4307 (3)1.1994 (4)0.0907 (3)0.0535 (11)
H210.44511.23890.03970.064*
C220.4008 (3)1.0974 (4)0.0996 (2)0.0508 (10)
H220.39671.06780.05490.061*
C230.3286 (4)0.8737 (3)0.2547 (2)0.0484 (11)
H23A0.28000.91260.28620.058*
H23B0.39690.85620.28190.058*
C240.2811 (3)0.7703 (3)0.2477 (2)0.0335 (7)
C25−0.1736 (4)0.7864 (3)0.4493 (2)0.0498 (10)
C26−0.2615 (3)0.8525 (3)0.4155 (3)0.0514 (10)
H26−0.26770.87090.36020.062*
C27−0.3402 (3)0.8912 (3)0.4640 (2)0.0439 (9)
H27−0.39790.93740.44120.053*
C28−0.3331 (3)0.8612 (3)0.5466 (2)0.0410 (8)
H28−0.38570.88740.57930.049*
C29−0.2472 (3)0.7921 (3)0.5800 (2)0.0440 (9)
H29−0.24300.77080.63530.053*
C30−0.1684 (3)0.7548 (4)0.5324 (2)0.0461 (9)
H30−0.11110.70820.55560.055*
C31−0.0959 (3)0.7740 (3)0.3230 (2)0.0464 (9)
H31A−0.09510.85110.30610.056*
H31B−0.16330.75440.30630.056*
C32−0.0029 (3)0.7204 (3)0.28230 (19)0.0360 (8)
C330.1833 (3)0.9173 (3)0.0287 (2)0.0370 (8)
H330.23240.90840.06950.044*
C340.1832 (3)1.0099 (3)−0.0315 (2)0.0450 (9)
H340.23071.0612−0.03040.054*
C350.1116 (3)1.0241 (3)−0.0925 (2)0.0446 (9)
H350.10991.0854−0.13310.054*
C360.0412 (3)0.9455 (3)−0.0928 (2)0.0389 (8)
C370.0465 (3)0.8542 (3)−0.02921 (19)0.0313 (7)
C38−0.0349 (3)0.9524 (3)−0.1547 (2)0.0484 (10)
H38−0.03971.0125−0.19640.058*
C39−0.0986 (3)0.8749 (3)−0.1535 (2)0.0400 (9)
H39−0.14800.8822−0.19400.048*
C40−0.0930 (3)0.7803 (3)−0.0912 (2)0.0404 (9)
C41−0.0215 (3)0.7696 (3)−0.0285 (2)0.0341 (7)
C42−0.1555 (3)0.6923 (3)−0.0897 (2)0.0398 (8)
H42−0.20460.6951−0.12960.048*
C43−0.1425 (3)0.6043 (4)−0.0292 (2)0.0494 (10)
H43−0.18040.5451−0.02870.059*
C44−0.0725 (3)0.6034 (3)0.0315 (2)0.0420 (8)
H44−0.06730.54390.07370.050*
C450.4660 (3)0.4104 (3)0.3261 (2)0.0489 (10)
H450.46300.42430.27060.059*
C460.5584 (3)0.3533 (4)0.3622 (2)0.0520 (11)
H460.61510.32900.33190.062*
C470.5625 (4)0.3341 (3)0.4441 (3)0.0555 (12)
H470.62320.29660.46970.067*
C480.4771 (3)0.3700 (3)0.4897 (3)0.0520 (11)
C490.4763 (3)0.3541 (3)0.5763 (3)0.0514 (11)
H490.53640.31930.60420.062*
C500.3923 (3)0.3878 (3)0.6161 (2)0.0427 (9)
H500.39400.37560.67150.051*
C510.2991 (3)0.4425 (3)0.5758 (2)0.0429 (9)
C520.2071 (3)0.4781 (3)0.6160 (2)0.0407 (9)
H520.20500.46600.67150.049*
C530.1195 (3)0.5313 (3)0.5726 (2)0.0430 (9)
H530.05740.55370.59860.052*
C540.1259 (4)0.5508 (4)0.4887 (2)0.0514 (10)
H540.06740.58790.45990.062*
C550.2979 (3)0.4632 (3)0.4909 (2)0.0407 (9)
C560.3875 (3)0.4251 (3)0.4477 (2)0.0396 (9)
C570.0849 (6)0.9332 (6)0.4635 (5)0.0479 (19)0.50
H57A0.03560.92780.42330.072*0.50
H57B0.11321.00220.45020.072*0.50
H57C0.04780.92500.51440.072*0.50
Mn10.10626 (4)0.68940 (4)0.13078 (3)0.03282 (14)
Mn20.23017 (4)0.55146 (4)0.31185 (3)0.03575 (15)
N10.1173 (2)0.8407 (2)0.03126 (18)0.0357 (6)
N2−0.0120 (2)0.6833 (2)0.03250 (16)0.0330 (6)
N30.3823 (3)0.4459 (2)0.36634 (18)0.0380 (7)
N40.2115 (3)0.5187 (2)0.44880 (17)0.0392 (7)
O10.0482 (2)0.5285 (2)0.18646 (15)0.0429 (6)
O20.1310 (2)0.4354 (2)0.29637 (15)0.0419 (6)
O30.23937 (19)0.6113 (2)0.08234 (13)0.0364 (5)
O40.3193 (2)0.5381 (2)0.19865 (14)0.0407 (6)
O50.2302 (2)0.7683 (2)0.18841 (14)0.0422 (6)
O60.2997 (2)0.6956 (2)0.30779 (14)0.0421 (6)
O7−0.0072 (2)0.7512 (2)0.20771 (14)0.0419 (6)
O80.0669 (2)0.6563 (2)0.32082 (14)0.0429 (6)
O9−0.0808 (2)0.3710 (2)0.18956 (16)0.0488 (7)
O100.5155 (2)0.5172 (2)0.11822 (17)0.0502 (7)
O110.34476 (19)0.93894 (19)0.17765 (14)0.0364 (5)
O12−0.0909 (2)0.7446 (2)0.40745 (14)0.0436 (6)
O130.1737 (5)0.8490 (6)0.4676 (4)0.0653 (17)0.50
H13A0.14930.79180.46780.098*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0321 (18)0.047 (2)0.048 (2)−0.0083 (16)0.0017 (16)−0.0154 (17)
C20.039 (2)0.064 (3)0.059 (3)−0.0034 (19)−0.0030 (19)−0.020 (2)
C30.041 (2)0.047 (2)0.0373 (19)−0.0152 (16)−0.0023 (16)−0.0153 (16)
C40.052 (2)0.048 (2)0.040 (2)−0.0109 (18)0.0000 (17)−0.0187 (17)
C50.047 (2)0.069 (3)0.041 (2)−0.036 (2)0.0106 (18)−0.0006 (19)
C60.054 (2)0.063 (3)0.042 (2)−0.028 (2)−0.0052 (19)−0.0007 (19)
C70.046 (2)0.040 (2)0.038 (2)−0.0128 (17)−0.0056 (16)−0.0006 (16)
C80.0352 (18)0.0359 (18)0.0220 (16)−0.0106 (14)0.0027 (13)−0.0045 (13)
C90.0341 (18)0.0407 (19)0.0306 (18)−0.0041 (14)0.0080 (14)−0.0066 (14)
C100.0315 (18)0.041 (2)0.043 (2)0.0055 (15)0.0025 (15)−0.0088 (16)
C110.0355 (19)0.055 (2)0.0354 (19)−0.0203 (17)0.0029 (15)−0.0103 (16)
C120.043 (2)0.039 (2)0.051 (2)−0.0162 (17)0.0105 (18)−0.0062 (17)
C130.040 (2)0.0389 (19)0.0410 (19)−0.0214 (15)0.0001 (15)−0.0022 (15)
C140.041 (2)0.052 (2)0.036 (2)−0.0127 (17)0.0000 (16)0.0011 (17)
C150.046 (2)0.0366 (19)0.0373 (19)−0.0051 (15)0.0008 (16)−0.0141 (15)
C160.0316 (17)0.0262 (16)0.0341 (19)−0.0034 (13)−0.0061 (14)−0.0027 (13)
C170.0369 (19)0.0340 (19)0.046 (2)−0.0066 (14)−0.0044 (16)−0.0050 (15)
C180.044 (2)0.048 (2)0.051 (2)−0.0303 (18)0.0025 (18)−0.0148 (18)
C190.0401 (19)0.055 (2)0.050 (2)−0.0270 (17)0.0058 (16)−0.0336 (19)
C200.063 (3)0.035 (2)0.045 (2)−0.0208 (18)0.0022 (19)−0.0008 (16)
C210.040 (2)0.060 (3)0.052 (2)−0.0241 (19)−0.0029 (18)0.014 (2)
C220.054 (2)0.058 (3)0.042 (2)−0.022 (2)0.0002 (18)−0.0060 (18)
C230.078 (3)0.035 (2)0.0332 (19)−0.0255 (19)−0.0205 (19)0.0022 (15)
C240.0406 (19)0.0219 (16)0.0368 (19)−0.0077 (13)−0.0052 (15)−0.0008 (14)
C250.057 (2)0.049 (2)0.042 (2)−0.0091 (19)0.0114 (18)−0.0055 (17)
C260.050 (2)0.041 (2)0.058 (3)0.0090 (18)0.0098 (19)−0.0052 (18)
C270.041 (2)0.042 (2)0.046 (2)0.0180 (16)0.0153 (17)−0.0147 (17)
C280.043 (2)0.042 (2)0.039 (2)−0.0013 (16)0.0110 (16)−0.0127 (16)
C290.047 (2)0.045 (2)0.043 (2)−0.0116 (17)0.0154 (17)−0.0158 (17)
C300.038 (2)0.064 (3)0.038 (2)−0.0127 (18)0.0077 (16)−0.0131 (18)
C310.049 (2)0.050 (2)0.038 (2)−0.0007 (18)0.0033 (17)−0.0077 (17)
C320.047 (2)0.0372 (19)0.0220 (16)−0.0050 (15)−0.0011 (14)−0.0018 (14)
C330.0399 (19)0.0396 (19)0.0289 (17)−0.0075 (15)−0.0081 (14)0.0014 (14)
C340.047 (2)0.041 (2)0.042 (2)−0.0131 (17)−0.0026 (17)0.0049 (16)
C350.047 (2)0.044 (2)0.035 (2)−0.0064 (17)−0.0016 (17)0.0102 (16)
C360.046 (2)0.040 (2)0.0242 (17)0.0077 (16)−0.0019 (15)0.0005 (14)
C370.0304 (17)0.0383 (18)0.0235 (16)0.0053 (14)0.0006 (13)−0.0070 (13)
C380.054 (2)0.050 (2)0.034 (2)0.0077 (19)−0.0127 (17)0.0049 (17)
C390.042 (2)0.044 (2)0.0320 (18)0.0144 (17)−0.0149 (15)−0.0081 (15)
C400.0336 (18)0.060 (2)0.0252 (17)0.0065 (17)−0.0031 (14)−0.0077 (16)
C410.0268 (16)0.0376 (19)0.0351 (18)−0.0027 (13)−0.0019 (13)−0.0017 (14)
C420.0388 (19)0.048 (2)0.041 (2)−0.0062 (16)−0.0086 (16)−0.0249 (17)
C430.044 (2)0.062 (3)0.044 (2)−0.0156 (19)−0.0107 (18)−0.0097 (19)
C440.043 (2)0.052 (2)0.0322 (19)−0.0139 (17)−0.0020 (16)−0.0065 (16)
C450.058 (3)0.045 (2)0.045 (2)−0.0003 (19)−0.022 (2)−0.0084 (18)
C460.052 (2)0.061 (3)0.044 (2)0.008 (2)−0.0162 (19)−0.015 (2)
C470.061 (3)0.045 (2)0.059 (3)−0.0033 (19)−0.044 (2)0.0002 (19)
C480.049 (2)0.041 (2)0.063 (3)−0.0059 (18)−0.028 (2)0.0015 (19)
C490.033 (2)0.053 (2)0.060 (3)−0.0105 (17)−0.0170 (19)0.011 (2)
C500.036 (2)0.044 (2)0.041 (2)−0.0145 (16)−0.0165 (16)0.0147 (16)
C510.045 (2)0.047 (2)0.0339 (19)−0.0225 (17)−0.0198 (16)0.0090 (16)
C520.040 (2)0.043 (2)0.039 (2)−0.0278 (16)−0.0008 (16)0.0012 (16)
C530.051 (2)0.042 (2)0.037 (2)−0.0132 (17)−0.0002 (17)−0.0077 (16)
C540.058 (3)0.062 (3)0.0269 (19)−0.006 (2)−0.0062 (17)0.0067 (17)
C550.048 (2)0.0348 (18)0.0367 (19)−0.0167 (16)−0.0159 (16)0.0060 (15)
C560.053 (2)0.0313 (18)0.0329 (18)−0.0128 (16)−0.0225 (17)0.0052 (14)
C570.035 (4)0.043 (4)0.055 (5)−0.009 (3)−0.008 (3)0.016 (3)
Mn10.0289 (3)0.0314 (3)0.0355 (3)−0.0038 (2)−0.0041 (2)0.0000 (2)
Mn20.0364 (3)0.0314 (3)0.0366 (3)−0.0078 (2)−0.0083 (2)0.0024 (2)
N10.0320 (15)0.0337 (15)0.0381 (16)0.0000 (12)−0.0022 (12)−0.0015 (12)
N20.0281 (14)0.0394 (16)0.0318 (15)−0.0061 (12)−0.0016 (12)−0.0064 (12)
N30.0462 (17)0.0304 (15)0.0382 (16)−0.0065 (13)−0.0141 (14)−0.0050 (12)
N40.0487 (18)0.0388 (17)0.0282 (15)−0.0106 (14)−0.0076 (13)0.0009 (12)
O10.0521 (15)0.0384 (14)0.0366 (14)−0.0138 (12)−0.0076 (12)0.0012 (11)
O20.0519 (15)0.0366 (14)0.0357 (13)−0.0156 (11)−0.0117 (12)0.0026 (10)
O30.0327 (12)0.0483 (15)0.0283 (12)0.0008 (11)−0.0049 (10)−0.0093 (10)
O40.0439 (14)0.0495 (15)0.0262 (13)0.0004 (11)−0.0043 (10)−0.0038 (11)
O50.0565 (16)0.0384 (14)0.0318 (13)−0.0130 (12)−0.0175 (12)−0.0012 (10)
O60.0509 (15)0.0380 (14)0.0333 (13)−0.0109 (11)−0.0137 (11)0.0066 (11)
O70.0435 (14)0.0519 (16)0.0258 (13)0.0047 (12)−0.0031 (10)−0.0016 (11)
O80.0459 (15)0.0510 (16)0.0263 (12)0.0064 (12)−0.0057 (11)0.0000 (11)
O90.0467 (15)0.0524 (16)0.0472 (16)−0.0239 (13)−0.0109 (12)−0.0003 (12)
O100.0340 (14)0.0604 (18)0.0550 (17)0.0028 (12)−0.0024 (12)−0.0129 (14)
O110.0392 (13)0.0359 (13)0.0351 (13)−0.0214 (10)−0.0053 (10)−0.0017 (10)
O120.0621 (17)0.0379 (14)0.0248 (12)0.0096 (12)0.0077 (11)−0.0011 (10)
O130.055 (4)0.069 (4)0.077 (5)−0.015 (3)0.019 (3)−0.026 (4)

Geometric parameters (Å, °)

C1—O91.374 (3)C31—H31B0.9700
C1—C21.3900C32—O81.243 (4)
C1—C61.3900C32—O71.255 (4)
C2—C31.3900C33—N11.332 (5)
C2—H20.9300C33—C341.394 (5)
C3—C41.3900C33—H330.9300
C3—H30.9300C34—C351.372 (5)
C4—C51.3900C34—H340.9300
C4—H40.9300C35—C361.399 (6)
C5—C61.3900C35—H350.9300
C5—H50.9300C36—C371.415 (5)
C6—H60.9300C36—C381.434 (5)
C7—O91.415 (4)C37—N11.361 (4)
C7—C81.521 (5)C37—C411.436 (5)
C7—H7A0.9700C38—C391.327 (6)
C7—H7B0.9700C38—H380.9300
C8—O11.234 (4)C39—C401.429 (5)
C8—O21.256 (4)C39—H390.9300
C9—O101.358 (5)C40—C411.400 (5)
C9—C141.378 (5)C40—C421.425 (5)
C9—C101.402 (5)C41—N21.347 (4)
C10—C111.379 (5)C42—C431.358 (6)
C10—H100.9300C42—H420.9300
C11—C121.356 (5)C43—C441.382 (5)
C11—H110.9300C43—H430.9300
C12—C131.390 (5)C44—N21.332 (5)
C12—H120.9300C44—H440.9300
C13—C141.391 (5)C45—N31.327 (5)
C13—H130.9300C45—C461.396 (5)
C14—H140.9300C45—H450.9300
C15—O101.418 (4)C46—C471.374 (6)
C15—C161.533 (5)C46—H460.9300
C15—H15A0.9700C47—C481.397 (7)
C15—H15B0.9700C47—H470.9300
C16—O41.247 (4)C48—C561.401 (5)
C16—O31.254 (4)C48—C491.452 (6)
C17—C221.364 (6)C49—C501.315 (6)
C17—O111.371 (4)C49—H490.9300
C17—C181.408 (5)C50—C511.422 (5)
C18—C191.354 (5)C50—H500.9300
C18—H180.9300C51—C521.405 (6)
C19—C201.364 (6)C51—C551.421 (5)
C19—H190.9300C52—C531.385 (5)
C20—C211.361 (6)C52—H520.9300
C20—H200.9300C53—C541.405 (5)
C21—C221.369 (6)C53—H530.9300
C21—H210.9300C54—N41.324 (5)
C22—H220.9300C54—H540.9300
C23—O111.419 (4)C55—N41.373 (5)
C23—C241.532 (5)C55—C561.421 (6)
C23—H23A0.9700C56—N31.365 (5)
C23—H23B0.9700C57—O131.465 (10)
C24—O51.227 (4)C57—H57A0.9600
C24—O61.257 (4)C57—H57B0.9600
C25—O121.366 (5)C57—H57C0.9600
C25—C261.385 (6)Mn1—O12.250 (3)
C25—C301.397 (6)Mn1—O32.094 (2)
C26—C271.386 (5)Mn1—O52.289 (2)
C26—H260.9300Mn1—O72.112 (3)
C27—C281.388 (5)Mn1—N12.299 (3)
C27—H270.9300Mn1—N22.302 (3)
C28—C291.382 (6)Mn2—O22.087 (2)
C28—H280.9300Mn2—O42.227 (3)
C29—C301.369 (5)Mn2—O62.102 (2)
C29—H290.9300Mn2—O82.351 (3)
C30—H300.9300Mn2—N32.327 (3)
C31—O121.417 (4)Mn2—N42.299 (3)
C31—C321.515 (5)O13—H13A0.8200
C31—H31A0.9700
O9—C1—C2115.15 (19)N1—C37—C41117.6 (3)
O9—C1—C6124.84 (19)C36—C37—C41120.0 (3)
C2—C1—C6120.0C39—C38—C36121.3 (4)
C3—C2—C1120.0C39—C38—H38119.3
C3—C2—H2120.0C36—C38—H38119.3
C1—C2—H2120.0C38—C39—C40121.4 (3)
C2—C3—C4120.0C38—C39—H39119.3
C2—C3—H3120.0C40—C39—H39119.3
C4—C3—H3120.0C41—C40—C42116.6 (3)
C3—C4—C5120.0C41—C40—C39120.0 (4)
C3—C4—H4120.0C42—C40—C39123.4 (3)
C5—C4—H4120.0N2—C41—C40123.4 (3)
C6—C5—C4120.0N2—C41—C37117.9 (3)
C6—C5—H5120.0C40—C41—C37118.7 (3)
C4—C5—H5120.0C43—C42—C40119.3 (3)
C5—C6—C1120.0C43—C42—H42120.4
C5—C6—H6120.0C40—C42—H42120.4
C1—C6—H6120.0C42—C43—C44119.6 (4)
O9—C7—C8111.8 (3)C42—C43—H43120.2
O9—C7—H7A109.3C44—C43—H43120.2
C8—C7—H7A109.3N2—C44—C43123.3 (4)
O9—C7—H7B109.3N2—C44—H44118.3
C8—C7—H7B109.3C43—C44—H44118.3
H7A—C7—H7B107.9N3—C45—C46123.8 (4)
O1—C8—O2127.6 (3)N3—C45—H45118.1
O1—C8—C7120.6 (3)C46—C45—H45118.1
O2—C8—C7111.9 (3)C47—C46—C45117.6 (4)
O10—C9—C14125.8 (3)C47—C46—H46121.2
O10—C9—C10115.7 (3)C45—C46—H46121.2
C14—C9—C10118.4 (3)C46—C47—C48121.3 (4)
C11—C10—C9120.0 (3)C46—C47—H47119.4
C11—C10—H10120.0C48—C47—H47119.4
C9—C10—H10120.0C47—C48—C56116.6 (4)
C12—C11—C10121.3 (4)C47—C48—C49124.4 (4)
C12—C11—H11119.3C56—C48—C49119.0 (4)
C10—C11—H11119.3C50—C49—C48121.5 (4)
C11—C12—C13119.6 (3)C50—C49—H49119.2
C11—C12—H12120.2C48—C49—H49119.2
C13—C12—H12120.2C49—C50—C51121.2 (4)
C12—C13—C14119.7 (4)C49—C50—H50119.4
C12—C13—H13120.2C51—C50—H50119.4
C14—C13—H13120.2C52—C51—C55117.8 (3)
C9—C14—C13120.9 (4)C52—C51—C50123.0 (3)
C9—C14—H14119.6C55—C51—C50119.2 (4)
C13—C14—H14119.6C53—C52—C51119.7 (3)
O10—C15—C16115.2 (3)C53—C52—H52120.1
O10—C15—H15A108.5C51—C52—H52120.1
C16—C15—H15A108.5C52—C53—C54118.9 (4)
O10—C15—H15B108.5C52—C53—H53120.6
C16—C15—H15B108.5C54—C53—H53120.6
H15A—C15—H15B107.5N4—C54—C53123.0 (4)
O4—C16—O3127.3 (3)N4—C54—H54118.5
O4—C16—C15119.7 (3)C53—C54—H54118.5
O3—C16—C15113.0 (3)N4—C55—C56118.6 (3)
C22—C17—O11116.7 (3)N4—C55—C51121.6 (4)
C22—C17—C18119.2 (4)C56—C55—C51119.8 (3)
O11—C17—C18124.1 (3)N3—C56—C48123.1 (4)
C19—C18—C17118.3 (4)N3—C56—C55117.7 (3)
C19—C18—H18120.8C48—C56—C55119.2 (4)
C17—C18—H18120.8O13—C57—H57A109.5
C18—C19—C20122.9 (3)O13—C57—H57B109.5
C18—C19—H19118.6H57A—C57—H57B109.5
C20—C19—H19118.6O13—C57—H57C109.5
C21—C20—C19117.9 (4)H57A—C57—H57C109.5
C21—C20—H20121.1H57B—C57—H57C109.5
C19—C20—H20121.1O3—Mn1—O7165.10 (9)
C20—C21—C22121.6 (4)O3—Mn1—O189.02 (10)
C20—C21—H21119.2O7—Mn1—O185.90 (10)
C22—C21—H21119.2O3—Mn1—O585.75 (10)
C17—C22—C21120.0 (4)O7—Mn1—O585.38 (10)
C17—C22—H22120.0O1—Mn1—O5123.41 (9)
C21—C22—H22120.0O3—Mn1—N191.36 (10)
O11—C23—C24110.2 (3)O7—Mn1—N199.24 (10)
O11—C23—H23A109.6O1—Mn1—N1154.47 (10)
C24—C23—H23A109.6O5—Mn1—N182.06 (9)
O11—C23—H23B109.6O3—Mn1—N296.27 (9)
C24—C23—H23B109.6O7—Mn1—N296.98 (10)
H23A—C23—H23B108.1O1—Mn1—N282.86 (10)
O5—C24—O6127.7 (3)O5—Mn1—N2153.72 (10)
O5—C24—C23119.8 (3)N1—Mn1—N271.72 (10)
O6—C24—C23112.5 (3)O2—Mn2—O6164.69 (10)
O12—C25—C26125.1 (4)O2—Mn2—O490.14 (10)
O12—C25—C30115.6 (4)O6—Mn2—O488.70 (10)
C26—C25—C30119.2 (4)O2—Mn2—N495.76 (10)
C25—C26—C27120.1 (4)O6—Mn2—N492.14 (10)
C25—C26—H26120.0O4—Mn2—N4153.09 (11)
C27—C26—H26120.0O2—Mn2—N3101.55 (10)
C26—C27—C28120.2 (4)O6—Mn2—N393.36 (10)
C26—C27—H27119.9O4—Mn2—N381.30 (10)
C28—C27—H27119.9N4—Mn2—N371.79 (11)
C29—C28—C27119.4 (3)O2—Mn2—O884.33 (10)
C29—C28—H28120.3O6—Mn2—O883.89 (10)
C27—C28—H28120.3O4—Mn2—O8125.25 (9)
C30—C29—C28120.7 (4)N4—Mn2—O881.54 (10)
C30—C29—H29119.6N3—Mn2—O8153.09 (10)
C28—C29—H29119.6C33—N1—C37117.5 (3)
C29—C30—C25120.3 (4)C33—N1—Mn1126.4 (2)
C29—C30—H30119.9C37—N1—Mn1116.1 (2)
C25—C30—H30119.9C44—N2—C41117.7 (3)
O12—C31—C32112.3 (3)C44—N2—Mn1125.9 (2)
O12—C31—H31A109.1C41—N2—Mn1116.4 (2)
C32—C31—H31A109.1C45—N3—C56117.7 (3)
O12—C31—H31B109.1C45—N3—Mn2126.5 (2)
C32—C31—H31B109.1C56—N3—Mn2115.7 (3)
H31A—C31—H31B107.9C54—N4—C55118.9 (3)
O8—C32—O7127.1 (3)C54—N4—Mn2125.1 (2)
O8—C32—C31122.1 (3)C55—N4—Mn2116.0 (3)
O7—C32—C31110.8 (3)C8—O1—Mn1143.6 (2)
N1—C33—C34123.9 (3)C8—O2—Mn2123.9 (2)
N1—C33—H33118.0C16—O3—Mn1121.8 (2)
C34—C33—H33118.0C16—O4—Mn2144.6 (2)
C35—C34—C33118.8 (4)C24—O5—Mn1148.5 (2)
C35—C34—H34120.6C24—O6—Mn2117.4 (2)
C33—C34—H34120.6C32—O7—Mn1121.6 (2)
C34—C35—C36119.4 (3)C32—O8—Mn2145.0 (2)
C34—C35—H35120.3C1—O9—C7116.4 (3)
C36—C35—H35120.3C9—O10—C15116.7 (3)
C35—C36—C37118.0 (3)C17—O11—C23117.4 (3)
C35—C36—C38123.4 (3)C25—O12—C31116.4 (3)
C37—C36—C38118.6 (4)C57—O13—H13A109.5
N1—C37—C36122.3 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C20—H20···O10i0.932.703.627 (5)175

Symmetry codes: (i) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2151).

References

  • Bruker (2000). SMART (Version 5.0), SAINT (Version 6.02a), SADABS (Version 2.01) and SHELXTL (Version 6.10). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Jiang, G.-Q., Li, Y.-Z., Hua, W.-J., Song, Y., Bai, J.-F., Li, S.-H., Scheer, M. & You, X.-Z. (2006). CrystEngComm, 8, 384–387.
  • Jiang, G.-Q., Li, Y.-Z., Wang, S.-N., Li, F.-F., Xu, Z.-J. & Bai, J.-F. (2005). Acta Cryst. E61, m1517–m1519.
  • Sessoli, R., Tsai, H. L., Schake, A. R., Wang, S., Vincent, J. B., Folting, K., Gatteschi, D., Christou, G. & Hendrickson, D. N. (1993). J. Am. Chem. Soc.115, 1804–1816.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Yaghi, O. M., Davis, C. E., Li, G. & Li, H. (1997). J. Am. Chem. Soc.119, 2861–2868.

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