metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

aInstitut für Anorganische Chemie, Christian-Albrechts-Universität Kiel, Max-Eyth Strasse 2, D-24098 Kiel, Germany
*Correspondence e-mail: cnaether@ac.uni-kiel.de

(Received 9 February 2009; accepted 13 March 2009; online 25 March 2009)

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[Boeckmann, J., Jess, I. & Näther, C. (2009). Acta Cryst. E65, m122.]). For related structures, see Zheng et al. (2005[Zheng, X.-J., Jin, L.-P., Gao, S. & Lu, S.-Z. (2005). New J. Chem. pp. 798-804.]).

[Scheme 1]

Experimental

Crystal data
  • [Mn(C12H6O4)(C10H8N2)]

  • Mr = 425.29

  • Monoclinic, P 21 /n

  • 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[Stoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.929, Tmax = 0.953

  • 45141 measured reflections

  • 7902 independent reflections

  • 6545 reflections with I > 2σ(I)

  • Rint = 0.057

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 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[Stoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg, 2008[Brandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: XCIF in SHELXTL.

Supporting information


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 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 top
Stoe IPDS-II
diffractometer
7902 independent reflections
Radiation source: fine-focus sealed tube6545 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 0.150 pixels mm-1θmax = 26.8°, θmin = 1.4°
ω scansh = 1213
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2008)
k = 3838
Tmin = 0.929, Tmax = 0.953l = 1414
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 Å3
0 restraintsΔρmin = 0.36 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.17Δρmax = 0.31 e Å3
7902 reflectionsΔρmin = 0.36 e Å3
523 parameters
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)
C120.0020 (3)0.64949 (10)0.7354 (3)0.0368 (7)
O30.0702 (2)0.62131 (8)0.6830 (2)0.0501 (6)
O40.0424 (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)
H490.59480.70370.01700.054*
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, º) 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, y1/2, z+3/2; (iv) x, y, z1; (v) x1, y, z; (vi) x+3/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Mn(C12H6O4)(C10H8N2)]
Mr425.29
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)10.5567 (3), 30.1870 (6), 11.6879 (3)
β (°) 93.734 (2)
V3)3716.74 (16)
Z8
Radiation typeMo Kα
µ (mm1)0.74
Crystal size (mm)0.14 × 0.08 × 0.06
Data collection
DiffractometerStoe IPDS-II
diffractometer
Absorption correctionNumerical
(X-SHAPE and X-RED32; Stoe & Cie, 2008)
Tmin, Tmax0.929, 0.953
No. of measured, independent and
observed [I > 2σ(I)] reflections
45141, 7902, 6545
Rint0.057
(sin θ/λ)max1)0.634
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.119, 1.17
No. of reflections7902
No. of parameters523
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.36

Computer programs: X-AREA (Stoe & Cie, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2008) and XP in SHELXTL (Sheldrick, 2008), XCIF in SHELXTL (Sheldrick, 2008).

 

Acknowledgements

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.

References

First citationBoeckmann, J., Jess, I. & Näther, C. (2009). Acta Cryst. E65, m122.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBrandenburg, K. (2008). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.  Google Scholar
First citationZheng, X.-J., Jin, L.-P., Gao, S. & Lu, S.-Z. (2005). New J. Chem. pp. 798–804.  Web of Science CSD CrossRef Google Scholar

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