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Acta Cryst. (2007). E63, m2283    [ doi:10.1107/S160053680703766X ]

Tetraaquabis(4,4'-bipyridine)manganese(II) pyridine-2,6-dicarboxylate tetrahydrate

Y.-X. Gao, L.-B. Wang and Y.-L. Niu

Abstract top

The title compound, [Mn(C10H8N2)2(H2O)4](C7H3NO4)·4H2O, prepared by hydrothermal synthesis, is isostructural with its FeII analogue. The compound contains isolated tetraaquabis(4,4'-bipyridine)manganese(II) cations, with two 4,4'-bipyridine molecules bound to MnII in a trans manner. The cations lie in layers, with pyridine-2,6-dicarboxylate dianions and water molecules forming an extensive hydrogen-bond network between them. The cations exhibit noncrystallographic inversion symmetry. The crystal was a partial inversion twin.

Comment top

The title compound is isostructural with its FeII analogue (Gao et al., 2007). In the [Mn(C10H8N2)2(H2O)4]2+ cations, MnII is hexacoordinated in an octahedral manner by four water molecules in the equatorial plane and two N atoms in the axial positions from two 4,4'-bipyridine molecules (Figure 1). The Mn—N and Mn—O bond lengths are in the range 2.284 (4)–2.291 (4) and 2.144 (3)–2.222 (3) Å, respectively. The cations lie in layers in the bc planes. Pyridine-2,6-dicarboxylate anions and water molecules lie between these layers, forming an extensive hydrogen-bond network (Figure 2).

Related literature top

For the analogous FeII compound, see: Gao et al. (2007).

Experimental top

A mixture of MnSO4 (0.5 mmol), pyridine-2,6-dicarboxylic acid (0.5 mmol), NaOH (1 mmol), 4,4'-bipyridine (0.5 mmol), H2O (8 ml) and ethanol (8 ml) were placed in a 25 ml Teflon-lined stainless steel autoclave and heated at 433 K for two days. On cooling to room temperature, pale pink crystals were obtained with a yield of 12%. Elemental analysis calculated: C 47.89, H 5.17, N 10.35%; found: C 47.87, H 5.21, N 10.33%.

Refinement top

H atoms bound to C atoms were placed geometrically and refined as riding with C—H= 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms of the water molecules were located from difference Fourier maps and were refined with distance restraints of O—H = 0.82 (1) Å and H···H = 1.35 (2) Å, and with Uiso(H) = 1.5Ueq(O). The [Mn(C10H8N2)2(H2O)4]2+ cations exhibit non-crystallographic inversion symmetry. The refined Flack parameter (Flack, 1983) from 530 Freidel pairs is 0.39 (3).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Packing diagram showing hydrogen bonds as dashed lines.
Tetraaquabis(4,4'-bipyridine)manganese(II) pyridine-2,6-dicarboxylate tetrahydrate top
Crystal data top
[Mn(C10H8N2)2(H2O)4](C7H3NO4)·4H2OF(000) = 1412
Mr = 676.54Dx = 1.434 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 3349 reflections
a = 18.407 (2) Åθ = 1.6–25.2°
b = 6.8231 (10) ŵ = 0.49 mm−1
c = 25.2925 (10) ÅT = 293 K
β = 99.40 (2)°Cube, pink
V = 3133.9 (6) Å30.15 × 0.15 × 0.15 mm
Z = 4
Data collection top
Bruker APEX II CCD
diffractometer		3349 independent reflections
Radiation source: fine-focus sealed tube2946 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 25.2°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −19→21
Tmin = 0.930, Tmax = 0.930k = −8→4
5104 measured reflectionsl = −29→12
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091 w = 1/[σ2(Fo2) + (0.0566P)2 + 0.8622P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3349 reflectionsΔρmax = 0.33 e Å−3
455 parametersΔρmin = −0.25 e Å−3
26 restraintsAbsolute structure: Flack (1983), 530 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.39 (3)
Crystal data top
[Mn(C10H8N2)2(H2O)4](C7H3NO4)·4H2OV = 3133.9 (6) Å3
Mr = 676.54Z = 4
Monoclinic, CcMo Kα radiation
a = 18.407 (2) ŵ = 0.49 mm−1
b = 6.8231 (10) ÅT = 293 K
c = 25.2925 (10) Å0.15 × 0.15 × 0.15 mm
β = 99.40 (2)°
Data collection top
Bruker APEX II CCD
diffractometer		3349 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		2946 reflections with I > 2σ(I)
Tmin = 0.930, Tmax = 0.930Rint = 0.018
5104 measured reflectionsθmax = 25.2°
Refinement top
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.091Δρmax = 0.33 e Å−3
S = 1.05Δρmin = −0.25 e Å−3
3349 reflectionsAbsolute structure: Flack (1983), 530 Friedel pairs
455 parametersFlack parameter: 0.39 (3)
26 restraints
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
Mn10.82217 (6)0.73736 (8)0.62273 (5)0.03257 (14)
C10.5731 (2)0.1741 (6)0.81919 (19)0.0408 (10)
C20.5712 (5)0.2656 (5)0.8731 (3)0.0358 (7)
C30.5691 (3)0.4672 (5)0.8799 (2)0.0421 (10)
H3A0.56800.54910.85040.050*
C40.5684 (2)0.5490 (6)0.93058 (18)0.0434 (10)
H4A0.56650.68440.93420.052*
C50.5706 (2)0.4305 (6)0.97556 (17)0.0414 (9)
H5A0.57040.48721.00900.050*
C60.5732 (3)0.2276 (6)0.9708 (2)0.0363 (12)
C70.5791 (2)0.0999 (5)1.02024 (16)0.0370 (8)
C80.8772 (3)0.8253 (8)0.74589 (18)0.0497 (12)
H8A0.92220.81220.73400.060*
C90.8771 (2)0.8419 (7)0.80050 (18)0.0464 (11)
H9A0.92160.84190.82400.056*
C100.8112 (2)0.8586 (5)0.82070 (16)0.0301 (9)
C110.7466 (3)0.8699 (8)0.78146 (19)0.0500 (12)
H11A0.70100.88900.79190.060*
C120.7516 (3)0.8527 (8)0.72754 (19)0.0520 (13)
H12A0.70830.85910.70280.062*
C130.8082 (2)0.8624 (5)0.87922 (16)0.0310 (9)
C140.8729 (3)0.8650 (6)0.91719 (16)0.0396 (10)
H14A0.91870.86550.90630.048*
C150.8674 (3)0.8669 (6)0.97181 (18)0.0424 (11)
H15A0.91080.86820.99650.051*
C160.7425 (3)0.8638 (7)0.95350 (18)0.0474 (11)
H16A0.69750.86230.96570.057*
C170.7411 (3)0.8627 (6)0.89898 (18)0.0421 (10)
H17A0.69650.86230.87560.051*
C180.8957 (2)0.6419 (6)0.51675 (17)0.0412 (10)
H18A0.93980.64100.54070.049*
C190.8986 (3)0.6322 (7)0.46217 (16)0.0436 (11)
H19A0.94370.62370.45030.052*
C200.8331 (2)0.6353 (5)0.42529 (16)0.0309 (9)
C210.7675 (3)0.6402 (7)0.44593 (18)0.0438 (11)
H21A0.72250.63830.42300.053*
C220.7698 (3)0.6477 (7)0.50062 (19)0.0473 (11)
H22A0.72520.64960.51340.057*
C230.8328 (2)0.6382 (5)0.36570 (16)0.0315 (9)
C240.7671 (3)0.6310 (7)0.32853 (19)0.0495 (12)
H24A0.72210.62290.34060.059*
C250.7691 (3)0.6360 (7)0.27403 (19)0.0502 (12)
H25A0.72470.63040.25050.060*
C260.8949 (3)0.6552 (8)0.2887 (2)0.0598 (14)
H26A0.93910.66300.27540.072*
C270.8980 (3)0.6511 (7)0.34413 (19)0.0489 (12)
H27A0.94320.65700.36670.059*
N10.5734 (2)0.1475 (6)0.91978 (18)0.0500 (10)
N20.8152 (2)0.8273 (5)0.70905 (14)0.0366 (8)
N30.8036 (2)0.8668 (5)0.99039 (14)0.0402 (9)
N40.83172 (19)0.6525 (5)0.53679 (13)0.0347 (8)
N50.8318 (2)0.6486 (5)0.25320 (15)0.0449 (9)
O10.7849 (2)1.0206 (4)0.59321 (13)0.0497 (8)
H110.760 (3)1.104 (6)0.6050 (19)0.075*
H120.796 (3)1.064 (7)0.5654 (14)0.075*
O20.93765 (18)0.8415 (4)0.63048 (14)0.0485 (8)
H210.948 (3)0.958 (2)0.630 (2)0.073*
H220.9748 (18)0.785 (6)0.645 (2)0.073*
O30.8599 (2)0.4530 (4)0.65233 (13)0.0515 (8)
H310.894 (2)0.388 (7)0.646 (2)0.077*
H320.851 (3)0.420 (8)0.6814 (12)0.077*
O40.70691 (17)0.6294 (4)0.61365 (13)0.0436 (7)
H410.693 (2)0.514 (2)0.613 (2)0.065*
H420.6709 (18)0.694 (5)0.600 (2)0.065*
O50.4858 (3)0.7285 (6)0.6359 (2)0.0613 (13)
H510.511 (3)0.737 (9)0.6122 (17)0.092*
H520.514 (3)0.722 (10)0.6646 (12)0.092*
O60.5642 (3)0.6923 (6)0.73882 (15)0.0740 (10)
H610.566 (4)0.769 (8)0.7639 (18)0.111*
H620.597 (3)0.611 (8)0.747 (3)0.111*
O70.5641 (2)0.1488 (5)0.68155 (14)0.0581 (10)
H710.571 (4)0.179 (7)0.7135 (7)0.087*
H720.548 (3)0.037 (4)0.680 (2)0.087*
O80.6591 (3)0.2453 (4)0.60733 (18)0.0517 (12)
H810.638 (3)0.222 (8)0.6326 (14)0.078*
H820.634 (3)0.204 (8)0.5802 (12)0.078*
O90.5725 (3)0.2894 (6)0.77983 (15)0.0566 (11)
O100.57394 (19)−0.0066 (4)0.81609 (12)0.0498 (8)
O110.58120 (19)0.1830 (5)1.06520 (12)0.0499 (8)
O120.58386 (18)−0.0786 (4)1.01351 (12)0.0484 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0349 (2)0.0397 (3)0.0231 (2)0.0010 (3)0.00508 (16)0.0010 (2)
C10.030 (2)0.050 (2)0.041 (2)0.0043 (19)0.0021 (18)−0.001 (2)
C20.0228 (13)0.0455 (16)0.0374 (15)0.002 (2)0.0003 (11)0.005 (2)
C30.0371 (18)0.0439 (17)0.043 (3)0.002 (2)−0.0005 (18)0.0038 (19)
C40.042 (2)0.0342 (19)0.052 (3)0.0047 (18)0.0020 (19)−0.0038 (18)
C50.038 (2)0.044 (2)0.040 (2)0.0005 (18)0.0026 (17)−0.0120 (19)
C60.029 (2)0.043 (2)0.037 (3)−0.0019 (18)0.006 (2)−0.0073 (18)
C70.0320 (19)0.046 (2)0.034 (2)−0.0036 (17)0.0075 (16)−0.0073 (17)
C80.034 (3)0.087 (3)0.031 (2)−0.004 (2)0.011 (2)−0.007 (2)
C90.026 (2)0.081 (3)0.029 (2)−0.001 (2)−0.001 (2)−0.005 (2)
C100.033 (2)0.0304 (17)0.027 (2)0.0008 (16)0.0053 (18)−0.0010 (15)
C110.032 (3)0.081 (3)0.040 (3)0.008 (2)0.012 (2)−0.009 (2)
C120.041 (3)0.082 (3)0.031 (3)0.014 (2)0.001 (2)−0.005 (2)
C130.036 (3)0.0260 (16)0.030 (2)0.0016 (16)0.0035 (19)−0.0032 (15)
C140.038 (3)0.059 (2)0.023 (2)0.000 (2)0.007 (2)−0.0020 (18)
C150.040 (3)0.052 (2)0.031 (2)−0.004 (2)−0.005 (2)−0.0027 (18)
C160.046 (3)0.060 (3)0.039 (3)0.003 (2)0.016 (2)0.001 (2)
C170.037 (3)0.058 (2)0.033 (2)0.003 (2)0.008 (2)−0.0036 (19)
C180.033 (2)0.061 (3)0.028 (2)0.009 (2)−0.0001 (19)−0.0049 (19)
C190.036 (3)0.070 (3)0.024 (2)0.005 (2)0.004 (2)−0.004 (2)
C200.038 (2)0.0291 (17)0.025 (2)0.0008 (16)0.0048 (18)−0.0019 (15)
C210.033 (3)0.069 (3)0.029 (2)−0.007 (2)0.003 (2)−0.007 (2)
C220.035 (3)0.074 (3)0.033 (2)−0.007 (2)0.008 (2)−0.007 (2)
C230.039 (2)0.0308 (17)0.027 (2)0.0023 (17)0.0116 (18)−0.0018 (15)
C240.036 (3)0.074 (3)0.039 (3)0.003 (2)0.008 (2)0.001 (2)
C250.050 (3)0.070 (3)0.031 (3)0.003 (2)0.008 (2)0.000 (2)
C260.057 (3)0.091 (4)0.036 (3)−0.007 (3)0.022 (3)−0.008 (3)
C270.037 (3)0.074 (3)0.036 (3)−0.004 (2)0.007 (2)−0.005 (2)
N10.039 (2)0.058 (2)0.052 (2)0.0024 (19)0.0071 (18)−0.0018 (19)
N20.038 (2)0.0420 (18)0.030 (2)0.0026 (16)0.0047 (16)−0.0013 (15)
N30.053 (2)0.0439 (18)0.0256 (19)0.0023 (16)0.0104 (17)−0.0004 (15)
N40.037 (2)0.0417 (19)0.0257 (19)−0.0023 (15)0.0047 (16)−0.0021 (15)
N50.058 (3)0.0468 (19)0.031 (2)−0.0045 (18)0.0106 (18)−0.0048 (16)
O10.067 (2)0.0500 (17)0.0366 (18)0.0176 (16)0.0209 (16)0.0105 (14)
O20.0414 (19)0.0535 (16)0.050 (2)−0.0056 (15)0.0066 (16)−0.0030 (15)
O30.075 (3)0.0473 (16)0.0361 (17)0.0218 (16)0.0209 (17)0.0117 (14)
O40.0395 (19)0.0456 (15)0.0449 (18)−0.0041 (13)0.0041 (15)0.0012 (14)
O50.059 (3)0.068 (2)0.062 (3)0.0074 (19)0.026 (3)0.0148 (19)
O60.088 (3)0.084 (3)0.050 (2)−0.005 (2)0.0095 (19)−0.011 (2)
O70.074 (3)0.053 (2)0.048 (2)−0.0077 (18)0.015 (2)−0.0040 (16)
O80.054 (3)0.055 (2)0.047 (3)−0.0064 (15)0.012 (2)−0.0069 (15)
O90.072 (3)0.0643 (19)0.033 (2)0.007 (2)0.0086 (19)0.0020 (18)
O100.061 (2)0.0491 (17)0.0388 (16)0.0013 (15)0.0053 (14)−0.0098 (14)
O110.056 (2)0.0596 (18)0.0355 (18)−0.0070 (16)0.0117 (15)−0.0124 (15)
O120.0629 (19)0.0427 (15)0.0390 (16)0.0005 (15)0.0065 (14)0.0000 (13)
Geometric parameters (Å, º) top
Mn1—O12.144 (3)C16—H16A0.930
Mn1—O32.153 (3)C17—H17A0.930
Mn1—O22.219 (4)C18—N41.357 (6)
Mn1—O42.222 (3)C18—C191.392 (6)
Mn1—N42.284 (4)C18—H18A0.930
Mn1—N22.291 (4)C19—C201.399 (6)
C1—O101.236 (5)C19—H19A0.930
C1—O91.267 (6)C20—C211.392 (6)
C1—C21.504 (9)C20—C231.506 (5)
C2—C31.388 (5)C21—C221.378 (6)
C2—N11.425 (8)C21—H21A0.930
C3—C41.400 (7)C22—N41.340 (6)
C3—H3A0.930C22—H22A0.930
C4—C51.391 (6)C23—C271.399 (7)
C4—H4A0.930C23—C241.407 (7)
C5—C61.391 (5)C24—C251.385 (7)
C5—H5A0.930C24—H24A0.930
C6—N11.402 (6)C25—N51.349 (7)
C6—C71.514 (6)C25—H25A0.930
C7—O121.235 (4)C26—N51.347 (7)
C7—O111.265 (5)C26—C271.395 (7)
C8—N21.350 (6)C26—H26A0.930
C8—C91.386 (6)C27—H27A0.930
C8—H8A0.930O1—H110.82 (1)
C9—C101.396 (6)O1—H120.82 (1)
C9—H9A0.930O2—H210.82 (1)
C10—C111.421 (6)O2—H220.82 (1)
C10—C131.490 (5)O3—H310.82 (1)
C11—C121.387 (7)O3—H320.81 (1)
C11—H11A0.930O4—H410.83 (1)
C12—N21.341 (6)O4—H420.82 (1)
C12—H12A0.930O5—H510.82 (1)
C13—C141.402 (6)O5—H520.82 (1)
C13—C171.406 (6)O6—H610.82 (1)
C14—C151.401 (6)O6—H620.82 (1)
C14—H14A0.930O7—H710.82 (1)
C15—N31.334 (7)O7—H720.82 (1)
C15—H15A0.930O8—H810.82 (1)
C16—N31.340 (6)O8—H820.82 (1)
C16—C171.375 (6)
O1—Mn1—O3179.8 (2)N3—C16—H16A117.5
O1—Mn1—O289.39 (13)C17—C16—H16A117.5
O3—Mn1—O290.46 (15)C16—C17—C13118.9 (4)
O1—Mn1—O490.98 (14)C16—C17—H17A120.6
O3—Mn1—O489.17 (14)C13—C17—H17A120.6
O2—Mn1—O4178.88 (16)N4—C18—C19123.3 (4)
O1—Mn1—N488.12 (13)N4—C18—H18A118.4
O3—Mn1—N491.82 (12)C19—C18—H18A118.4
O2—Mn1—N486.78 (14)C18—C19—C20119.5 (4)
O4—Mn1—N492.18 (14)C18—C19—H19A120.3
O1—Mn1—N291.49 (13)C20—C19—H19A120.3
O3—Mn1—N288.57 (13)C21—C20—C19117.1 (4)
O2—Mn1—N291.84 (14)C21—C20—C23120.9 (4)
O4—Mn1—N289.20 (14)C19—C20—C23121.9 (4)
N4—Mn1—N2178.57 (17)C22—C21—C20119.4 (4)
O10—C1—O9124.6 (5)C22—C21—H21A120.3
O10—C1—C2118.3 (4)C20—C21—H21A120.3
O9—C1—C2117.1 (4)N4—C22—C21124.8 (5)
C3—C2—N1117.0 (6)N4—C22—H22A117.6
C3—C2—C1122.0 (6)C21—C22—H22A117.6
N1—C2—C1121.0 (3)C27—C23—C24116.1 (4)
C2—C3—C4120.9 (5)C27—C23—C20121.9 (4)
C2—C3—H3A119.5C24—C23—C20122.0 (4)
C4—C3—H3A119.5C25—C24—C23120.3 (5)
C5—C4—C3120.9 (4)C25—C24—H24A119.9
C5—C4—H4A119.5C23—C24—H24A119.9
C3—C4—H4A119.5N5—C25—C24123.6 (5)
C4—C5—C6120.3 (4)N5—C25—H25A118.2
C4—C5—H5A119.9C24—C25—H25A118.2
C6—C5—H5A119.9N5—C26—C27123.9 (5)
C5—C6—N1118.3 (4)N5—C26—H26A118.1
C5—C6—C7120.0 (4)C27—C26—H26A118.1
N1—C6—C7121.7 (3)C26—C27—C23119.8 (5)
O12—C7—O11125.0 (4)C26—C27—H27A120.1
O12—C7—C6116.8 (3)C23—C27—H27A120.1
O11—C7—C6118.2 (4)C6—N1—C2122.6 (4)
N2—C8—C9123.3 (4)C12—N2—C8116.6 (4)
N2—C8—H8A118.4C12—N2—Mn1123.7 (3)
C9—C8—H8A118.4C8—N2—Mn1118.8 (3)
C8—C9—C10120.9 (4)C15—N3—C16116.3 (4)
C8—C9—H9A119.5C22—N4—C18115.9 (4)
C10—C9—H9A119.5C22—N4—Mn1117.8 (3)
C9—C10—C11115.3 (4)C18—N4—Mn1125.1 (3)
C9—C10—C13122.7 (4)C26—N5—C25116.3 (4)
C11—C10—C13122.0 (4)Mn1—O1—H11132 (3)
C12—C11—C10120.0 (4)Mn1—O1—H12121 (3)
C12—C11—H11A120.0H11—O1—H12107 (2)
C10—C11—H11A120.0Mn1—O2—H21122 (3)
N2—C12—C11123.8 (4)Mn1—O2—H22127 (4)
N2—C12—H12A118.1H21—O2—H22107 (2)
C11—C12—H12A118.1Mn1—O3—H31130 (4)
C14—C13—C17116.9 (4)Mn1—O3—H32117 (3)
C14—C13—C10121.0 (4)H31—O3—H32109 (2)
C17—C13—C10122.0 (4)Mn1—O4—H41127 (3)
C15—C14—C13119.1 (4)Mn1—O4—H42124 (3)
C15—C14—H14A120.5H41—O4—H42103 (2)
C13—C14—H14A120.5H51—O5—H52107 (2)
N3—C15—C14123.8 (4)H61—O6—H62107 (2)
N3—C15—H15A118.1H71—O7—H72107 (2)
C14—C15—H15A118.1H81—O8—H82108 (2)
N3—C16—C17125.0 (5)
O10—C1—C2—C3−179.0 (6)C19—C20—C23—C24176.6 (4)
O9—C1—C2—C3−0.1 (10)C27—C23—C24—C250.3 (7)
O10—C1—C2—N12.4 (10)C20—C23—C24—C25179.4 (4)
O9—C1—C2—N1−178.6 (5)C23—C24—C25—N5−0.3 (8)
N1—C2—C3—C4−0.5 (10)N5—C26—C27—C230.4 (8)
C1—C2—C3—C4−179.1 (5)C24—C23—C27—C26−0.3 (7)
C2—C3—C4—C50.6 (8)C20—C23—C27—C26−179.4 (4)
C3—C4—C5—C6−0.3 (7)C5—C6—N1—C20.2 (8)
C4—C5—C6—N1−0.1 (7)C7—C6—N1—C2−177.1 (5)
C4—C5—C6—C7177.2 (4)C3—C2—N1—C60.1 (10)
C5—C6—C7—O12−177.5 (4)C1—C2—N1—C6178.7 (5)
N1—C6—C7—O12−0.3 (6)C11—C12—N2—C8−2.2 (7)
C5—C6—C7—O110.4 (7)C11—C12—N2—Mn1167.2 (4)
N1—C6—C7—O11177.6 (4)C9—C8—N2—C122.1 (7)
N2—C8—C9—C101.1 (8)C9—C8—N2—Mn1−167.9 (4)
C8—C9—C10—C11−3.9 (7)O1—Mn1—N2—C1272.0 (4)
C8—C9—C10—C13175.5 (4)O3—Mn1—N2—C12−108.2 (4)
C9—C10—C11—C123.8 (7)O2—Mn1—N2—C12161.4 (4)
C13—C10—C11—C12−175.7 (4)O4—Mn1—N2—C12−19.0 (4)
C10—C11—C12—N2−0.8 (8)O1—Mn1—N2—C8−118.9 (4)
C9—C10—C13—C145.2 (6)O3—Mn1—N2—C861.0 (4)
C11—C10—C13—C14−175.4 (4)O2—Mn1—N2—C8−29.4 (4)
C9—C10—C13—C17−174.6 (4)O4—Mn1—N2—C8150.2 (4)
C11—C10—C13—C174.8 (6)C14—C15—N3—C160.3 (6)
C17—C13—C14—C150.3 (6)C17—C16—N3—C15−0.7 (7)
C10—C13—C14—C15−179.5 (4)C21—C22—N4—C18−2.4 (7)
C13—C14—C15—N3−0.2 (7)C21—C22—N4—Mn1165.7 (4)
N3—C16—C17—C130.8 (7)C19—C18—N4—C221.8 (6)
C14—C13—C17—C16−0.6 (6)C19—C18—N4—Mn1−165.4 (3)
C10—C13—C17—C16179.2 (4)O1—Mn1—N4—C22−63.9 (3)
N4—C18—C19—C200.7 (7)O3—Mn1—N4—C22116.2 (3)
C18—C19—C20—C21−2.5 (6)O2—Mn1—N4—C22−153.4 (3)
C18—C19—C20—C23176.0 (4)O4—Mn1—N4—C2227.0 (3)
C19—C20—C21—C222.0 (6)O1—Mn1—N4—C18103.0 (3)
C23—C20—C21—C22−176.6 (4)O3—Mn1—N4—C18−76.8 (3)
C20—C21—C22—N40.6 (7)O2—Mn1—N4—C1813.6 (3)
C21—C20—C23—C27174.2 (4)O4—Mn1—N4—C18−166.0 (3)
C19—C20—C23—C27−4.3 (6)C27—C26—N5—C25−0.4 (8)
C21—C20—C23—C24−4.9 (6)C24—C25—N5—C260.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O8i0.82 (1)2.10 (3)2.848 (6)152 (6)
O1—H12···N3ii0.82 (1)1.98 (2)2.787 (5)167 (6)
O2—H21···O5iii0.82 (1)1.97 (1)2.781 (5)171 (5)
O2—H22···O7iii0.82 (1)1.98 (1)2.799 (5)179 (7)
O3—H31···O5iv0.82 (1)2.05 (1)2.864 (6)175 (6)
O3—H32···N5v0.81 (1)1.96 (1)2.772 (5)177 (7)
O4—H41···O80.83 (1)1.93 (1)2.760 (4)177 (5)
O4—H42···O11vi0.82 (1)1.93 (1)2.751 (4)173 (5)
O5—H52···O60.82 (1)1.96 (2)2.773 (7)169 (6)
O5—H51···O11vi0.82 (1)1.97 (2)2.770 (6)165 (6)
O6—H62···O90.82 (1)2.41 (7)2.933 (6)123 (7)
O6—H61···O10i0.82 (1)2.01 (2)2.821 (5)169 (7)
O7—H72···O5vii0.82 (1)2.56 (2)3.330 (6)158 (5)
O7—H71···O90.82 (1)1.84 (2)2.645 (5)168 (6)
O8—H81···O70.82 (1)2.04 (2)2.844 (6)166 (6)
O8—H82···O12viii0.82 (1)1.98 (1)2.787 (5)172 (6)
Symmetry codes: (i) x, y+1, z; (ii) x, −y+2, z−1/2; (iii) x+1/2, y+1/2, z; (iv) x+1/2, y−1/2, z; (v) x, −y+1, z+1/2; (vi) x, −y+1, z−1/2; (vii) x, y−1, z; (viii) x, −y, z−1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H11···O8i0.82 (1)2.10 (3)2.848 (6)152 (6)
O1—H12···N3ii0.82 (1)1.98 (2)2.787 (5)167 (6)
O2—H21···O5iii0.82 (1)1.97 (1)2.781 (5)171 (5)
O2—H22···O7iii0.82 (1)1.98 (1)2.799 (5)179 (7)
O3—H31···O5iv0.82 (1)2.05 (1)2.864 (6)175 (6)
O3—H32···N5v0.81 (1)1.96 (1)2.772 (5)177 (7)
O4—H41···O80.83 (1)1.93 (1)2.760 (4)177 (5)
O4—H42···O11vi0.82 (1)1.93 (1)2.751 (4)173 (5)
O5—H52···O60.82 (1)1.96 (2)2.773 (7)169 (6)
O5—H51···O11vi0.82 (1)1.97 (2)2.770 (6)165 (6)
O6—H62···O90.82 (1)2.41 (7)2.933 (6)123 (7)
O6—H61···O10i0.82 (1)2.01 (2)2.821 (5)169 (7)
O7—H72···O5vii0.82 (1)2.56 (2)3.330 (6)158 (5)
O7—H71···O90.82 (1)1.84 (2)2.645 (5)168 (6)
O8—H81···O70.82 (1)2.04 (2)2.844 (6)166 (6)
O8—H82···O12viii0.82 (1)1.98 (1)2.787 (5)172 (6)
Symmetry codes: (i) x, y+1, z; (ii) x, −y+2, z−1/2; (iii) x+1/2, y+1/2, z; (iv) x+1/2, y−1/2, z; (v) x, −y+1, z+1/2; (vi) x, −y+1, z−1/2; (vii) x, y−1, z; (viii) x, −y, z−1/2.
Acknowledgements top

The authors thank the Natural Science Foundation of China (grant No. 20501017) and Tonghua Teachers' College.

references
References top

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Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Gao, Y.-X., Wang, L.-B. & Niu, Y.-L. (2007). Acta Cryst. E63, m1845–m1846.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.