PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): m421.
Published online 2009 March 25. doi:  10.1107/S1600536809009301
PMCID: PMC2968939

Poly[(μ-4,4′-bipyridine)(μ-naphthalene-1,4-dicarboxyl­ato)manganese(II)]

Abstract

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.

Related literature

For the isotypic structure with FeII, see Boeckmann et al. (2009 [triangle]). For related structures, see Zheng et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m421-scheme1.jpg

Experimental

Crystal data

  • [Mn(C12H6O4)(C10H8N2)]
  • M r = 425.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m421-efi2.jpg
  • a = 10.5567 (3) Å
  • b = 30.1870 (6) Å
  • c = 11.6879 (3) Å
  • β = 93.734 (2)°
  • V = 3716.74 (16) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.74 mm−1
  • T = 293 K
  • 0.14 × 0.08 × 0.06 mm

Data collection

  • Stoe IPDS-II diffractometer
  • Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008 [triangle]) T min = 0.929, T max = 0.953
  • 45141 measured reflections
  • 7902 independent reflections
  • 6545 reflections with I > 2σ(I)
  • R int = 0.057

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.119
  • S = 1.17
  • 7902 reflections
  • 523 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.36 e Å−3

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009301/bt2868sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009301/bt2868Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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.
Fig. 2.
: Crystal structure of the title compound with view onto the dimers. The 4,4'-bipyridine molecules are omitted for clarity.
Fig. 3.
: Crystal structure of the title compound with view in the direction of the crystallographic a axis.

Crystal data

[Mn(C12H6O4)(C10H8N2)]F(000) = 1736
Mr = 425.29Dx = 1.520 Mg m3
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 mm1
β = 93.734 (2)°T = 293 K
V = 3716.74 (16) Å3Blocks, colourless
Z = 80.14 × 0.08 × 0.06 mm

Data collection

Stoe IPDS-II diffractometer7902 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

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 = 1.17w = 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 Å3
0 restraintsΔρmin = −0.35 e Å3

Special details

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)

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)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2868).

References

  • Boeckmann, J., Jess, I. & Näther, C. (2009). Acta Cryst. E65, m122. [PMC free article] [PubMed]
  • Brandenburg, K. (2008). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • 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.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography