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Acta Cryst. (2009). E65, m421    [ doi:10.1107/S1600536809009301 ]

Poly[([mu]-4,4'-bipyridine)([mu]-naphthalene-1,4-dicarboxylato)manganese(II)]

J. Boeckmann, I. Jess and C. Näther

Abstract top

In the crystal structure of the title compound, [Mn(C12H6O4)(C10H8N2)]n, the Mn atoms are each coordinated by four O atoms of naphthalene-1,4-dicarboxylate anions and two N atoms of two symmetry-related 4,4'-bipyridine ligands within a strongly distorted octahedra. Two of the O atoms originate from one naphthalene-1,4-dicarboxylate anion, whereas the remaining two O atoms derive from two symmetry-equivalent naphthalene-1,4-dicarboxylate anions. Two Mn atoms are connected via the anions into dimers, which are further linked by the anions and the N-donor ligands into a three-dimensional coordination network.

Comment top

In our ongoing investigations on the synthesis of new metal-organic frameworks, we prepared the title compound, C22H14N2O4Mn, by the reaction of manganese(II)chloride with naphthalene-1,4-dicarboxylic acid in sodium hydroxide, sodium acetate, 4,4'- bipyridine and water. Poly[(µ-4,4'-bipyridine)(µ-naphthalene-1,4-dicarboxylato) manganese(II)] is isotypic to Poly[(µ-4,4'-bipyridine)(µ-naphthalene-1,4-dicarboxylato) iron(II)], reported recently (Boeckmann et al., 2009).

In the crystal structure of the title compound the manganese atoms are each surrounded by four O atoms of three symmetry related naphthalene-1,4-dicarboxylate anions and two N atoms of two 4,4'-bipyridine ligands related by symmetry within a distorted octahedral coordination environment (Fig 1). Two symmetry equivalent naphthalene-1,4-dicarboxylate anions bridges two symmetry related manganese atoms into dimers, which is located on a centre of inversion (Fig 2). Such dimers are also found in the structure of [Eu2(NDC)3(4,4'-bipyridine)0.5(H2O)3] . (4,4'-bipyridine) (Zheng et al., 2005). These dimanganese(II)-centered octahedra are connected via the naphthalene-1,4-dicarboxylate anions into layers, which are parallel to the a/b plane, and are further connected by the 4,4'-bipyridine ligands into a three-dimensional coordination network (Fig 3).

Related literature top

For an isotypic structure with FeII see Boeckmann et al. (2009). For related structures see Zheng et al. (2005).

Experimental top

16.2 mg MnCl2 . 2 H2O (0.10 mmol), 33.0 mg naphthalene-1,4-dicarboxylic acid (0.15 mmol), 10.4 mg NaOH (0.26 mmol), 40.0 mg NaAc . 3 H2O (0.30 mmol), 20.0 mg 4,4'-Bipyridine (0.10 mmol) and 5 ml of water were transfered into a glass tube and heated to 150° C for 4 d. On cooling colourless blocks of the title compound were obtained.

Refinement top

All H atoms were located in difference map but were positioned with idealized geometry and were refined isotropic with Ueq(H) = 1.2 Ueq(C) of the parent atom using a riding model with C—H = 0.93 Å.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-AREA (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2008) and XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. : Crystal structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level. Symmetry codes: i = x + 1, y, z; ii = x, y, z + 1; iii = -x + 1.5, y - 1/2, -z + 1.5; iv = x, y, z - 1.
[Figure 2] Fig. 2. : Crystal structure of the title compound with view onto the dimers. The 4,4'-bipyridine molecules are omitted for clarity.
[Figure 3] Fig. 3. : Crystal structure of the title compound with view in the direction of the crystallographic a axis.
Poly[(µ-4,4'-bipyridine)(µ-naphthalene-1,4-dicarboxylato)manganese(II)] top
Crystal data top
[Mn(C12H6O4)(C10H8N2)]F(000) = 1736
Mr = 425.29Dx = 1.520 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.5567 (3) ÅCell parameters from 43887 reflections
b = 30.1870 (6) Åθ = 1.4–27.2°
c = 11.6879 (3) ŵ = 0.74 mm−1
β = 93.734 (2)°T = 293 K
V = 3716.74 (16) Å3Blocks, colourless
Z = 80.14 × 0.08 × 0.06 mm
Data collection top
Stoe IPDS-II
diffractometer		7902 independent reflections
Radiation source: fine-focus sealed tube6545 reflections with I > 2σ(I)
graphiteRint = 0.057
Detector resolution: 0.150 pixels mm-1θmax = 26.8°, θmin = 1.4°
ω scansh = −12→13
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2008)		k = −38→38
Tmin = 0.929, Tmax = 0.953l = −14→14
45141 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + (0.0296P)2 + 4.295P]
where P = (Fo2 + 2Fc2)/3
7902 reflections(Δ/σ)max = 0.001
523 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.35 e Å−3
Crystal data top
[Mn(C12H6O4)(C10H8N2)]V = 3716.74 (16) Å3
Mr = 425.29Z = 8
Monoclinic, P21/nMo Kα radiation
a = 10.5567 (3) ŵ = 0.74 mm−1
b = 30.1870 (6) ÅT = 293 K
c = 11.6879 (3) Å0.14 × 0.08 × 0.06 mm
β = 93.734 (2)°
Data collection top
Stoe IPDS-II
diffractometer		7902 independent reflections
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2008)		6545 reflections with I > 2σ(I)
Tmin = 0.929, Tmax = 0.953Rint = 0.057
45141 measured reflectionsθmax = 26.8°
Refinement top
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.119Δρmax = 0.31 e Å−3
S = 1.17Δρmin = −0.35 e Å−3
7902 reflectionsAbsolute structure: ?
523 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.77819 (5)0.714006 (14)0.77976 (4)0.03123 (12)
Mn20.77185 (5)0.579806 (15)0.67513 (4)0.03472 (13)
C10.4084 (3)0.64521 (10)0.7166 (3)0.0379 (7)
C20.3428 (3)0.68342 (11)0.7357 (3)0.0461 (8)
H20.38710.70990.74510.055*
C30.2103 (3)0.68348 (11)0.7413 (3)0.0461 (8)
H30.16910.71020.75290.055*
C40.1404 (3)0.64549 (10)0.7302 (3)0.0373 (7)
C50.1409 (4)0.56271 (11)0.7086 (3)0.0495 (9)
H50.05360.56210.71510.059*
C60.2032 (4)0.52440 (12)0.6950 (4)0.0642 (12)
H60.15870.49780.69180.077*
C70.3352 (4)0.52436 (13)0.6856 (4)0.0680 (12)
H70.37780.49770.67620.082*
C80.4007 (4)0.56295 (11)0.6901 (4)0.0523 (9)
H80.48800.56240.68320.063*
C90.3398 (3)0.60406 (10)0.7049 (3)0.0387 (7)
C100.2049 (3)0.60412 (10)0.7135 (3)0.0386 (7)
C110.5509 (3)0.64903 (10)0.7160 (3)0.0352 (7)
O10.6003 (2)0.68148 (8)0.7687 (2)0.0457 (6)
O20.6110 (2)0.62049 (8)0.6641 (2)0.0463 (6)
C12−0.0020 (3)0.64949 (10)0.7354 (3)0.0368 (7)
O3−0.0702 (2)0.62131 (8)0.6830 (2)0.0501 (6)
O4−0.0424 (2)0.68245 (8)0.7874 (2)0.0458 (6)
C210.7452 (3)0.94371 (10)0.8155 (3)0.0389 (7)
C220.7282 (4)0.91782 (11)0.9088 (3)0.0498 (9)
H220.71050.93110.97780.060*
C230.7368 (4)0.87126 (11)0.9028 (3)0.0509 (9)
H230.72390.85440.96760.061*
C240.7635 (3)0.85071 (10)0.8037 (3)0.0386 (7)
C250.8072 (5)0.85703 (13)0.5973 (3)0.0615 (11)
H250.81480.82640.59210.074*
C260.8203 (6)0.88213 (15)0.5031 (4)0.0802 (16)
H260.83660.86860.43420.096*
C270.8095 (6)0.92831 (15)0.5079 (4)0.0797 (15)
H270.81810.94520.44230.096*
C280.7865 (4)0.94860 (13)0.6088 (3)0.0599 (11)
H280.78020.97930.61140.072*
C290.7719 (3)0.92355 (10)0.7098 (3)0.0400 (7)
C300.7822 (3)0.87639 (11)0.7040 (3)0.0412 (7)
C310.7350 (3)0.99366 (11)0.8236 (3)0.0408 (7)
O110.8342 (3)1.01602 (8)0.8250 (3)0.0649 (8)
O120.6298 (3)1.01132 (8)0.8259 (3)0.0669 (8)
C320.7718 (3)0.80079 (10)0.7979 (3)0.0373 (7)
O130.8766 (2)0.78240 (8)0.7851 (2)0.0543 (7)
O140.6728 (2)0.77859 (7)0.8027 (2)0.0507 (6)
C410.7782 (3)0.70738 (10)0.3422 (3)0.0364 (7)
C420.8900 (3)0.71117 (12)0.4116 (3)0.0460 (8)
H420.96810.71080.37900.055*
C430.8846 (3)0.71547 (12)0.5288 (3)0.0456 (8)
H430.96080.71790.57290.055*
N10.7771 (3)0.71640 (9)0.5828 (2)0.0416 (6)
C440.6697 (3)0.71320 (12)0.5159 (3)0.0446 (8)
H440.59310.71400.55090.054*
C450.6657 (3)0.70878 (12)0.3975 (3)0.0457 (8)
H450.58810.70680.35540.055*
C460.7791 (3)0.70395 (10)0.2152 (3)0.0352 (7)
C470.8908 (3)0.70268 (12)0.1596 (3)0.0448 (8)
H470.96850.70190.20190.054*
C480.8870 (3)0.70257 (12)0.0409 (3)0.0441 (8)
H480.96360.70150.00580.053*
N20.7797 (3)0.70391 (9)−0.0260 (2)0.0381 (6)
C490.6711 (3)0.70379 (12)0.0276 (3)0.0451 (8)
H490.59480.7037−0.01700.054*
C500.6665 (3)0.70380 (12)0.1455 (3)0.0437 (8)
H500.58860.70370.17840.052*
C510.7779 (4)0.58616 (12)1.1149 (3)0.0479 (9)
C520.8887 (5)0.58533 (18)1.0592 (3)0.0730 (13)
H520.96630.58691.10140.088*
C530.8857 (5)0.58219 (18)0.9417 (3)0.0723 (13)
H530.96260.58180.90710.087*
N110.7789 (4)0.57972 (10)0.8742 (3)0.0545 (8)
C540.6726 (5)0.58022 (16)0.9282 (3)0.0672 (12)
H540.59610.57840.88410.081*
C550.6677 (4)0.58323 (17)1.0459 (3)0.0678 (12)
H550.58970.58331.07850.081*
C560.7762 (4)0.58964 (11)1.2420 (3)0.0449 (8)
C570.8866 (4)0.58875 (13)1.3122 (3)0.0534 (9)
H570.96500.58851.28020.064*
C580.8804 (4)0.58820 (13)1.4301 (3)0.0530 (9)
H580.95610.58781.47550.064*
N120.7719 (3)0.58829 (10)1.4818 (2)0.0443 (7)
C590.6656 (4)0.59161 (13)1.4149 (3)0.0511 (9)
H590.58870.59341.44940.061*
C600.6638 (4)0.59256 (13)1.2964 (3)0.0526 (9)
H600.58700.59521.25320.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0340 (2)0.0311 (2)0.0289 (2)−0.00001 (19)0.00408 (18)−0.00152 (18)
Mn20.0400 (3)0.0316 (2)0.0329 (2)−0.0005 (2)0.0045 (2)−0.00109 (19)
C10.0354 (17)0.0374 (16)0.0410 (17)0.0000 (13)0.0039 (14)−0.0032 (13)
C20.042 (2)0.0347 (16)0.062 (2)−0.0048 (14)0.0056 (17)−0.0040 (15)
C30.042 (2)0.0347 (16)0.063 (2)0.0022 (14)0.0083 (17)−0.0052 (15)
C40.0351 (17)0.0382 (16)0.0393 (17)−0.0016 (13)0.0057 (13)−0.0017 (13)
C50.044 (2)0.0398 (18)0.065 (2)−0.0057 (15)0.0051 (18)−0.0009 (16)
C60.059 (3)0.0344 (18)0.100 (3)−0.0073 (18)0.007 (2)−0.002 (2)
C70.060 (3)0.0341 (19)0.110 (4)0.0034 (18)0.006 (3)−0.008 (2)
C80.042 (2)0.0408 (18)0.075 (3)0.0025 (16)0.0076 (18)−0.0083 (17)
C90.0406 (19)0.0347 (16)0.0414 (18)0.0005 (14)0.0060 (14)−0.0024 (13)
C100.0394 (18)0.0355 (16)0.0412 (18)−0.0019 (14)0.0054 (14)−0.0016 (13)
C110.0350 (17)0.0364 (16)0.0348 (16)−0.0006 (13)0.0054 (13)0.0010 (13)
O10.0406 (13)0.0516 (14)0.0451 (13)−0.0129 (11)0.0043 (11)−0.0106 (11)
O20.0399 (14)0.0461 (13)0.0538 (14)0.0064 (11)0.0099 (11)−0.0040 (11)
C120.0388 (18)0.0379 (16)0.0340 (16)0.0026 (14)0.0049 (13)0.0019 (13)
O30.0409 (14)0.0519 (14)0.0574 (15)−0.0083 (11)0.0015 (12)−0.0073 (12)
O40.0443 (14)0.0509 (14)0.0427 (13)0.0124 (11)0.0061 (11)−0.0067 (11)
C210.0413 (19)0.0321 (15)0.0434 (18)−0.0021 (14)0.0050 (14)−0.0012 (13)
C220.074 (3)0.0365 (17)0.0411 (19)0.0032 (17)0.0163 (18)−0.0036 (14)
C230.075 (3)0.0375 (17)0.0416 (19)0.0008 (17)0.0165 (18)0.0036 (14)
C240.0435 (19)0.0310 (15)0.0414 (18)0.0011 (14)0.0046 (14)0.0011 (13)
C250.101 (4)0.044 (2)0.040 (2)0.005 (2)0.013 (2)−0.0071 (16)
C260.144 (5)0.061 (3)0.038 (2)0.006 (3)0.019 (3)−0.0062 (19)
C270.137 (5)0.063 (3)0.040 (2)0.007 (3)0.018 (3)0.0100 (19)
C280.094 (3)0.0423 (19)0.044 (2)0.002 (2)0.010 (2)0.0055 (16)
C290.051 (2)0.0323 (15)0.0366 (17)−0.0012 (14)0.0050 (15)0.0009 (13)
C300.048 (2)0.0360 (16)0.0398 (18)0.0020 (15)0.0045 (15)−0.0024 (13)
C310.0459 (19)0.0382 (16)0.0388 (17)0.0023 (15)0.0062 (14)0.0027 (14)
O110.0525 (17)0.0349 (13)0.108 (2)−0.0048 (12)0.0090 (16)−0.0026 (14)
O120.0499 (17)0.0398 (14)0.111 (2)0.0052 (12)0.0075 (16)−0.0027 (15)
C320.0399 (18)0.0345 (15)0.0372 (17)−0.0013 (14)0.0006 (14)−0.0009 (13)
O130.0397 (14)0.0378 (13)0.086 (2)0.0007 (11)0.0052 (13)−0.0063 (12)
O140.0414 (14)0.0322 (12)0.0793 (18)−0.0012 (10)0.0098 (13)−0.0008 (11)
C410.0432 (18)0.0357 (15)0.0305 (16)0.0003 (14)0.0053 (13)0.0009 (12)
C420.0433 (19)0.061 (2)0.0342 (17)−0.0041 (17)0.0063 (15)0.0005 (15)
C430.0424 (19)0.061 (2)0.0333 (17)−0.0095 (17)0.0012 (14)0.0020 (15)
N10.0472 (17)0.0455 (15)0.0323 (14)−0.0010 (13)0.0037 (12)0.0007 (12)
C440.044 (2)0.057 (2)0.0329 (17)0.0068 (17)0.0064 (14)0.0026 (15)
C450.0421 (19)0.062 (2)0.0330 (17)0.0031 (17)0.0018 (14)0.0022 (15)
C460.0399 (17)0.0362 (16)0.0297 (15)0.0021 (13)0.0036 (13)−0.0003 (12)
C470.0386 (19)0.059 (2)0.0371 (18)0.0022 (16)0.0025 (14)−0.0031 (15)
C480.0404 (19)0.056 (2)0.0363 (17)−0.0008 (16)0.0069 (15)−0.0033 (15)
N20.0432 (16)0.0412 (14)0.0302 (13)0.0019 (12)0.0040 (12)0.0005 (11)
C490.0395 (19)0.060 (2)0.0354 (17)0.0020 (16)0.0018 (14)−0.0024 (15)
C500.0423 (19)0.056 (2)0.0333 (17)0.0012 (16)0.0057 (14)−0.0010 (15)
C510.067 (2)0.0435 (18)0.0336 (18)0.0036 (17)0.0047 (17)−0.0003 (14)
C520.066 (3)0.119 (4)0.034 (2)0.013 (3)0.0024 (19)−0.003 (2)
C530.071 (3)0.110 (4)0.038 (2)0.018 (3)0.009 (2)0.002 (2)
N110.078 (2)0.0488 (17)0.0371 (16)0.0022 (17)0.0070 (16)−0.0021 (13)
C540.073 (3)0.093 (3)0.035 (2)−0.017 (3)−0.0013 (19)−0.002 (2)
C550.063 (3)0.105 (4)0.035 (2)−0.010 (3)0.0047 (19)−0.003 (2)
C560.059 (2)0.0411 (17)0.0342 (17)0.0021 (16)0.0013 (16)−0.0009 (14)
C570.058 (2)0.065 (2)0.0385 (19)−0.0017 (19)0.0080 (17)−0.0020 (17)
C580.055 (2)0.068 (2)0.0354 (18)0.0002 (19)0.0027 (16)−0.0038 (17)
N120.0509 (18)0.0480 (16)0.0342 (15)0.0017 (14)0.0048 (13)−0.0009 (12)
C590.054 (2)0.062 (2)0.0375 (19)0.0018 (19)0.0056 (17)−0.0033 (16)
C600.059 (2)0.062 (2)0.0368 (19)0.0065 (19)0.0006 (17)−0.0018 (16)
Geometric parameters (Å, °) top
Mn1—O12.115 (2)C28—C291.418 (5)
Mn1—O4i2.116 (2)C28—H280.9300
Mn1—O142.269 (2)C29—C301.430 (4)
Mn1—N2ii2.290 (3)C31—O121.234 (4)
Mn1—N12.302 (3)C31—O111.245 (4)
Mn1—O132.310 (2)C31—Mn2vi2.602 (3)
Mn1—C322.629 (3)O11—Mn2vi2.227 (3)
Mn2—O3i2.083 (2)O12—Mn2vi2.314 (3)
Mn2—O22.093 (2)C32—O141.246 (4)
Mn2—O11iii2.227 (3)C32—O131.255 (4)
Mn2—N12iv2.274 (3)C41—C451.389 (5)
Mn2—O12iii2.314 (3)C41—C421.392 (5)
Mn2—N112.323 (3)C41—C461.489 (4)
Mn2—C31iii2.602 (3)C42—C431.381 (5)
C1—C21.371 (4)C42—H420.9300
C1—C91.440 (4)C43—N11.334 (4)
C1—C111.510 (4)C43—H430.9300
C2—C31.404 (5)N1—C441.338 (4)
C2—H20.9300C44—C451.389 (4)
C3—C41.365 (4)C44—H440.9300
C3—H30.9300C45—H450.9300
C4—C101.442 (4)C46—C471.384 (4)
C4—C121.514 (4)C46—C501.397 (5)
C5—C61.345 (5)C47—C481.386 (5)
C5—C101.420 (5)C47—H470.9300
C5—H50.9300C48—N21.334 (4)
C6—C71.406 (6)C48—H480.9300
C6—H60.9300N2—C491.341 (4)
C7—C81.354 (5)N2—Mn1iv2.290 (3)
C7—H70.9300C49—C501.383 (4)
C8—C91.413 (4)C49—H490.9300
C8—H80.9300C50—H500.9300
C9—C101.435 (5)C51—C551.374 (6)
C11—O21.251 (4)C51—C521.375 (6)
C11—O11.253 (4)C51—C561.490 (5)
C12—O31.248 (4)C52—C531.375 (5)
C12—O41.255 (4)C52—H520.9300
O3—Mn2v2.083 (2)C53—N111.335 (6)
O4—Mn1v2.116 (2)C53—H530.9300
C21—C221.364 (5)N11—C541.323 (5)
C21—C291.421 (4)C54—C551.383 (5)
C21—C311.515 (4)C54—H540.9300
C22—C231.411 (5)C55—H550.9300
C22—H220.9300C56—C571.381 (5)
C23—C241.360 (5)C56—C601.385 (5)
C23—H230.9300C57—C581.384 (5)
C24—C301.424 (4)C57—H570.9300
C24—C321.511 (4)C58—N121.330 (5)
C25—C261.351 (6)C58—H580.9300
C25—C301.417 (5)N12—C591.329 (5)
C25—H250.9300N12—Mn2ii2.274 (3)
C26—C271.400 (6)C59—C601.385 (5)
C26—H260.9300C59—H590.9300
C27—C281.365 (6)C60—H600.9300
C27—H270.9300
O1—Mn1—O4i125.59 (10)C28—C27—C26120.1 (4)
O1—Mn1—O1488.05 (9)C28—C27—H27120.0
O4i—Mn1—O14145.67 (10)C26—C27—H27120.0
O1—Mn1—N2ii86.99 (10)C27—C28—C29121.0 (4)
O4i—Mn1—N2ii87.11 (9)C27—C28—H28119.5
O14—Mn1—N2ii88.22 (10)C29—C28—H28119.5
O1—Mn1—N190.41 (10)C28—C29—C21122.2 (3)
O4i—Mn1—N190.15 (10)C28—C29—C30118.6 (3)
O14—Mn1—N196.94 (10)C21—C29—C30119.2 (3)
N2ii—Mn1—N1174.15 (10)C25—C30—C24122.6 (3)
O1—Mn1—O13144.32 (9)C25—C30—C29118.1 (3)
O4i—Mn1—O1390.08 (9)C24—C30—C29119.2 (3)
O14—Mn1—O1356.77 (9)O12—C31—O11121.5 (3)
N2ii—Mn1—O1396.79 (10)O12—C31—C21119.9 (3)
N1—Mn1—O1388.38 (10)O11—C31—C21118.5 (3)
O1—Mn1—C32116.11 (10)O12—C31—Mn2vi62.78 (18)
O4i—Mn1—C32118.19 (10)O11—C31—Mn2vi58.79 (18)
O14—Mn1—C3228.26 (9)C21—C31—Mn2vi175.7 (2)
N2ii—Mn1—C3292.94 (10)C31—O11—Mn2vi92.7 (2)
N1—Mn1—C3292.91 (10)C31—O12—Mn2vi88.9 (2)
O13—Mn1—C3228.52 (9)O14—C32—O13121.1 (3)
O3i—Mn2—O2107.09 (10)O14—C32—C24118.9 (3)
O3i—Mn2—O11iii157.06 (10)O13—C32—C24120.0 (3)
O2—Mn2—O11iii95.82 (10)O14—C32—Mn159.59 (16)
O3i—Mn2—N12iv85.66 (11)O13—C32—Mn161.49 (17)
O2—Mn2—N12iv85.71 (10)C24—C32—Mn1177.3 (2)
O11iii—Mn2—N12iv97.43 (11)C32—O13—Mn190.00 (19)
O3i—Mn2—O12iii100.34 (10)C32—O14—Mn192.2 (2)
O2—Mn2—O12iii152.43 (10)C45—C41—C42116.4 (3)
O11iii—Mn2—O12iii56.85 (10)C45—C41—C46121.8 (3)
N12iv—Mn2—O12iii93.79 (11)C42—C41—C46121.7 (3)
O3i—Mn2—N1189.02 (11)C43—C42—C41119.8 (3)
O2—Mn2—N1192.04 (11)C43—C42—H42120.1
O11iii—Mn2—N1189.03 (12)C41—C42—H42120.1
N12iv—Mn2—N11173.34 (11)N1—C43—C42124.3 (3)
O12iii—Mn2—N1191.11 (12)N1—C43—H43117.9
O3i—Mn2—C31iii128.57 (11)C42—C43—H43117.9
O2—Mn2—C31iii124.34 (11)C43—N1—C44115.9 (3)
O11iii—Mn2—C31iii28.56 (10)C43—N1—Mn1121.6 (2)
N12iv—Mn2—C31iii96.88 (11)C44—N1—Mn1122.0 (2)
O12iii—Mn2—C31iii28.30 (10)N1—C44—C45124.0 (3)
N11—Mn2—C31iii89.57 (11)N1—C44—H44118.0
C2—C1—C9119.1 (3)C45—C44—H44118.0
C2—C1—C11116.8 (3)C44—C45—C41119.7 (3)
C9—C1—C11124.1 (3)C44—C45—H45120.2
C1—C2—C3121.6 (3)C41—C45—H45120.2
C1—C2—H2119.2C47—C46—C50116.4 (3)
C3—C2—H2119.2C47—C46—C41122.1 (3)
C4—C3—C2121.9 (3)C50—C46—C41121.4 (3)
C4—C3—H3119.1C46—C47—C48120.1 (3)
C2—C3—H3119.1C46—C47—H47120.0
C3—C4—C10118.9 (3)C48—C47—H47120.0
C3—C4—C12117.5 (3)N2—C48—C47123.7 (3)
C10—C4—C12123.6 (3)N2—C48—H48118.2
C6—C5—C10121.8 (4)C47—C48—H48118.2
C6—C5—H5119.1C48—N2—C49116.5 (3)
C10—C5—H5119.1C48—N2—Mn1iv122.4 (2)
C5—C6—C7120.3 (4)C49—N2—Mn1iv120.8 (2)
C5—C6—H6119.8N2—C49—C50123.5 (3)
C7—C6—H6119.8N2—C49—H49118.3
C8—C7—C6120.2 (4)C50—C49—H49118.3
C8—C7—H7119.9C49—C50—C46119.9 (3)
C6—C7—H7119.9C49—C50—H50120.1
C7—C8—C9121.7 (4)C46—C50—H50120.1
C7—C8—H8119.1C55—C51—C52115.7 (3)
C9—C8—H8119.1C55—C51—C56121.7 (4)
C8—C9—C10118.1 (3)C52—C51—C56122.6 (4)
C8—C9—C1122.7 (3)C53—C52—C51120.6 (4)
C10—C9—C1119.2 (3)C53—C52—H52119.7
C5—C10—C9117.9 (3)C51—C52—H52119.7
C5—C10—C4122.7 (3)N11—C53—C52123.8 (4)
C9—C10—C4119.4 (3)N11—C53—H53118.1
O2—C11—O1124.7 (3)C52—C53—H53118.1
O2—C11—C1119.1 (3)C54—N11—C53115.4 (3)
O1—C11—C1116.2 (3)C54—N11—Mn2120.3 (3)
C11—O1—Mn1137.1 (2)C53—N11—Mn2124.2 (3)
C11—O2—Mn2144.0 (2)N11—C54—C55124.2 (4)
O3—C12—O4125.1 (3)N11—C54—H54117.9
O3—C12—C4117.9 (3)C55—C54—H54117.9
O4—C12—C4116.9 (3)C51—C55—C54120.2 (4)
C12—O3—Mn2v150.0 (2)C51—C55—H55119.9
C12—O4—Mn1v131.9 (2)C54—C55—H55119.9
C22—C21—C29119.6 (3)C57—C56—C60116.3 (3)
C22—C21—C31120.4 (3)C57—C56—C51121.8 (3)
C29—C21—C31120.0 (3)C60—C56—C51121.9 (3)
C21—C22—C23121.3 (3)C56—C57—C58120.0 (4)
C21—C22—H22119.4C56—C57—H57120.0
C23—C22—H22119.4C58—C57—H57120.0
C24—C23—C22121.0 (3)N12—C58—C57123.4 (4)
C24—C23—H23119.5N12—C58—H58118.3
C22—C23—H23119.5C57—C58—H58118.3
C23—C24—C30119.7 (3)C59—N12—C58116.9 (3)
C23—C24—C32120.6 (3)C59—N12—Mn2ii122.5 (2)
C30—C24—C32119.7 (3)C58—N12—Mn2ii120.5 (2)
C26—C25—C30121.4 (4)N12—C59—C60123.1 (4)
C26—C25—H25119.3N12—C59—H59118.5
C30—C25—H25119.3C60—C59—H59118.5
C25—C26—C27120.8 (4)C59—C60—C56120.1 (4)
C25—C26—H26119.6C59—C60—H60119.9
C27—C26—H26119.6C56—C60—H60119.9
Symmetry codes: (i) x+1, y, z; (ii) x, y, z+1; (iii) −x+3/2, y−1/2, −z+3/2; (iv) x, y, z−1; (v) x−1, y, z; (vi) −x+3/2, y+1/2, −z+3/2.
Acknowledgements top

This work was supported by the state of Schleswig-Holstein. The authors thank Professor Dr Wolfgang Bensch for allowing us to use his equipment.

references
References top

Boeckmann, J., Jess, I. & Näther, C. (2009). Acta Cryst. E65, m122.

Brandenburg, K. (2008). DIAMOND. Crystal Impact, Bonn, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Stoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.

Zheng, X.-J., Jin, L.-P., Gao, S. & Lu, S.-Z. (2005). New J. Chem. pp. 798–804.