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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1705.
Published online 2010 November 30. doi:  10.1107/S1600536810049433
PMCID: PMC3011697

cyclo-Tetra­kis(μ-naphthalene-1,8-dicarboxyl­ato)tetra­kis­[diaqua­(2,2′-bipyridine)­manganese(II)] tetra­hydrate

Abstract

In the title centrosymmetric tetra­nuclear complex, [Mn4(C12H6O4)4(C10H8N2)4(H2O)8]·4H2O, two independent MnII ions are coordinated in a slightly disorted octa­hedral environment by two aqua ligands, two naphthalene-1,8-dicarboxyl­ate (1,8-nap) ligands and one bis-chelating 2,2′-bipyridine (2,2′-bipy) ligand. In the crystal, mol­ecules are linked by inter­molecular O—H(...)O hydrogen bonds into chains along [100]. These chains are further linked by weak π–π inter­actions with centroid–centroid distances in the range of 3.609 (2)–3.758 (1) Å, forming a three-dimensional supra­molecular network.

Related literature

For related structures, see: Feng et al. (2008 [triangle]); Fu et al. (2010 [triangle]); Wen et al. (2007 [triangle], 2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1705-scheme1.jpg

Experimental

Crystal data

  • [Mn4(C12H6O4)4(C10H8N2)4(H2O)8]·4H2O
  • M r = 1917.36
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1705-efi1.jpg
  • a = 10.3323 (3) Å
  • b = 14.3847 (4) Å
  • c = 15.4299 (5) Å
  • α = 77.760 (2)°
  • β = 74.198 (2)°
  • γ = 76.009 (2)°
  • V = 2114.77 (11) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.67 mm−1
  • T = 296 K
  • 0.37 × 0.17 × 0.05 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.87, T max = 0.97
  • 32295 measured reflections
  • 9641 independent reflections
  • 6196 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.115
  • S = 1.06
  • 9641 reflections
  • 577 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.50 e Å−3
  • Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: DIAMOND (Brandenburg, 1999) [triangle]; software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810049433/lh5168sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049433/lh5168Isup2.hkl

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

supplementary crystallographic information

Comment

Presently, our studies are focused on selecting suitable multidentate ligands to construct novel coordination architectures. 1,8-Naphthalenecarboxylic anhydride, which is can be hydrolysed to naphthalene-1,8-dicarboxylate(1,8-nap) under hydrothermal conditions, is a versatile building block which can be used to construct interesting structures due to the potential variety of bridging abilities. Some complexes containing 1,8-nap have already been reported (Fu et al., 2010; Feng et al., 2008; Wen et al., 2008; Wen et al., 2007). Herein,we report a new Mn(II) complex containing a 1,8-nap ligand, [Mn4(1,8-nap)4(2,2'-bipy)4(H2O)8].4(H2O),(I).

The molecular structure of (I) is shown in Fig.1. The formula unit consists of four Mn atoms, four 1,8-nap anions, eight coordinated water molecules, two 2,2'-bipy and four lattice water molecules. Unique atoms Mn1 and Mn2 are six-coordinated and have slightly distorted octahedral coordination environments formed by two 1,8-nap ligands, two N atoms from one 2,2'-bipy and two water molecules. All carboxylate groups of the 1,8-nap ligands are deprotonated, and adopt a monodentate coordination mode. Each 1,8-nap ligand links two MnII ions and hence each MnII ion coordinates to two 1,8-nap ligands to form a [Mn4(1,8-nap)4] neutral ring. Four 2,2'-bipy ligands are oriented to the outer side of the ring while the aqua ligands point to the inside of the ring.

In the crystal structure, (Fig. 2) intermolecular O—H···O hydrogen bonds involving coordinated water molecules, solvent water molecules and carboxylate group oxygen atoms, link molecules to form a one-dimensional chain along [100]. In addition, weak π–π interactions with centroid-centroid distance in the range of 3.609 (2) to 3.758 (1) Å between symmetry related 2,2'-bipy ligands lead to the the formation of a three-dimensional network.

Experimental

A mixture of MnCl2(0.1003 g, 0.5 mmol), naphthalene-1,8-dicarboxylic anhydride (0.0991 g, 0.5 mmol), NaOH (0.0402 g, 1 mmol) and 2,2'-bipyridine (0.0378 g, 0.25 mmol) and ethanol-water (15 ml, V/V, 1:2) was sealed in a 25 ml stainless steel reactor with a Telflon liner and heated at 433 K for 72 h. On completion of the reaction, the reactor was cooled slowly to room temperature and the mixture was filtered, giving colourless block-shaped single crystals suitable for X-ray analysis.

Refinement

H-atoms were positioned geometrically and included in the refinement using a riding-model approximation [C–H = 0.93 and O–H = 'as found' positions] with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) -x+1, -y+1, -z+1]
Fig. 2.
Part of the crystal structure with green dashed lines to show the donor-acceptor distances of hydrogen bonds (H atoms are not shown) and pink lines to show the π–π interactions.

Crystal data

[Mn4(C12H6O4)4(C10H8N2)4(H2O)8]·4H2OZ = 1
Mr = 1917.36F(000) = 988
Triclinic, P1Dx = 1.506 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.3323 (3) ÅCell parameters from 5948 reflections
b = 14.3847 (4) Åθ = 1.5–27.6°
c = 15.4299 (5) ŵ = 0.67 mm1
α = 77.760 (2)°T = 296 K
β = 74.198 (2)°Block, colourless
γ = 76.009 (2)°0.37 × 0.17 × 0.05 mm
V = 2114.77 (11) Å3

Data collection

Bruker APEXII area-detector diffractometer9641 independent reflections
Radiation source: fine-focus sealed tube6196 reflections with I > 2σ(I)
graphiteRint = 0.041
ω scansθmax = 27.6°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→13
Tmin = 0.87, Tmax = 0.97k = −18→18
32295 measured reflectionsl = −19→20

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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0516P)2] where P = (Fo2 + 2Fc2)/3
9641 reflections(Δ/σ)max = 0.001
577 parametersΔρmax = 0.50 e Å3
3 restraintsΔρmin = −0.41 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
Mn10.25463 (4)0.76117 (3)0.46946 (2)0.03213 (11)
Mn20.38953 (4)0.49105 (3)0.78495 (2)0.03230 (12)
O10.25004 (16)0.79966 (12)0.59713 (10)0.0354 (4)
O1W0.46961 (17)0.77539 (13)0.42064 (12)0.0494 (5)
H1WA0.50290.74300.46480.074*
H1WB0.52190.75100.37560.074*
O20.46969 (17)0.73941 (15)0.59898 (12)0.0540 (5)
O2W0.2899 (2)0.61536 (13)0.54280 (11)0.0602 (6)
H2WA0.27490.60610.59910.090*
H2WB0.27690.56610.52900.090*
O30.03335 (18)0.65873 (13)0.73071 (13)0.0510 (5)
O3W0.50323 (18)0.48414 (14)0.64458 (11)0.0562 (5)
H3WA0.56750.43640.63440.084*
H3WB0.44540.52000.61670.084*
O40.25706 (16)0.61265 (11)0.72371 (10)0.0354 (4)
O4W0.22730 (17)0.40881 (13)0.79531 (12)0.0482 (5)
H4WA0.28590.35960.77350.072*
H4WB0.17490.42490.75970.072*
O50.52168 (16)0.35117 (12)0.81890 (11)0.0377 (4)
O5W0.2207 (3)0.47052 (17)0.48764 (16)0.0944 (8)
H5WA0.15090.49210.45300.142*
H5WB0.14490.46910.53790.142*
O60.43026 (18)0.26289 (13)0.75699 (12)0.0477 (5)
O6W0.05204 (19)0.48703 (14)0.67218 (14)0.0626 (6)
H6WA−0.02500.47300.68100.094*
H6WB0.03800.53950.68800.094*
O70.82217 (19)0.41392 (14)0.67703 (13)0.0521 (5)
O80.70690 (16)0.32143 (12)0.64178 (10)0.0357 (4)
N10.0249 (2)0.79384 (15)0.47871 (13)0.0358 (5)
N20.1971 (2)0.91457 (14)0.39807 (13)0.0344 (5)
N30.2996 (2)0.52060 (14)0.92913 (12)0.0346 (5)
N40.5154 (2)0.58391 (14)0.81433 (13)0.0359 (5)
C1−0.0580 (3)0.7300 (2)0.51645 (18)0.0473 (7)
H1A−0.02060.66850.54260.057*
C2−0.1956 (3)0.7512 (2)0.5184 (2)0.0566 (8)
H2A−0.24960.70470.54480.068*
C3−0.2516 (3)0.8414 (2)0.4810 (2)0.0588 (8)
H3A−0.34480.85770.48230.071*
C4−0.1689 (3)0.9084 (2)0.44113 (19)0.0496 (7)
H4A−0.20540.97020.41490.060*
C5−0.0304 (2)0.88263 (19)0.44059 (15)0.0341 (6)
C60.0646 (2)0.95046 (17)0.39762 (15)0.0311 (6)
C70.0205 (3)1.04443 (19)0.35954 (17)0.0430 (7)
H7A−0.07201.06760.36050.052*
C80.1140 (3)1.1040 (2)0.31990 (18)0.0475 (7)
H8A0.08571.16770.29380.057*
C90.2486 (3)1.0680 (2)0.31958 (19)0.0505 (7)
H9A0.31391.10650.29320.061*
C100.2862 (3)0.97346 (19)0.35893 (18)0.0446 (7)
H10A0.37840.94930.35830.053*
C110.3276 (2)0.81466 (19)0.72314 (16)0.0370 (6)
C120.4079 (3)0.8776 (2)0.7214 (2)0.0562 (8)
H12A0.47580.88950.66900.067*
C130.3931 (3)0.9251 (3)0.7948 (2)0.0705 (10)
H13A0.44840.96900.79050.085*
C140.2979 (3)0.9066 (2)0.8714 (2)0.0630 (9)
H14A0.28890.93700.92080.076*
C150.1091 (3)0.8272 (2)0.95932 (19)0.0625 (9)
H15A0.10450.85631.00880.075*
C160.0179 (4)0.7714 (2)0.96595 (19)0.0650 (9)
H16A−0.05090.76411.01880.078*
C170.0273 (3)0.7245 (2)0.89283 (18)0.0513 (7)
H17A−0.03700.68730.89720.062*
C180.1297 (3)0.73254 (18)0.81485 (16)0.0372 (6)
C190.2234 (2)0.79467 (18)0.80346 (16)0.0359 (6)
C200.2114 (3)0.8423 (2)0.87871 (17)0.0476 (7)
C210.3518 (3)0.77905 (18)0.63364 (16)0.0344 (6)
C220.1399 (3)0.66459 (18)0.75014 (16)0.0352 (6)
C230.1922 (3)0.48646 (19)0.98448 (16)0.0415 (6)
H23A0.15340.44630.96330.050*
C240.1356 (3)0.5076 (2)1.07131 (17)0.0500 (7)
H24A0.06000.48281.10770.060*
C250.1930 (3)0.5658 (2)1.10280 (17)0.0508 (7)
H25A0.15750.58101.16140.061*
C260.3036 (3)0.60142 (19)1.04707 (17)0.0457 (7)
H26A0.34400.64091.06780.055*
C270.3552 (2)0.57877 (17)0.95985 (16)0.0339 (6)
C280.4746 (2)0.61537 (18)0.89526 (16)0.0353 (6)
C290.5408 (3)0.6765 (2)0.91684 (19)0.0502 (7)
H29A0.51030.69790.97310.060*
C300.6526 (3)0.7058 (2)0.8545 (2)0.0595 (8)
H30A0.69860.74700.86810.071*
C310.6950 (3)0.6735 (2)0.7725 (2)0.0539 (8)
H31A0.77090.69180.72960.065*
C320.6240 (3)0.61362 (19)0.75418 (19)0.0444 (7)
H32A0.65240.59270.69770.053*
C330.6221 (3)0.18375 (19)0.81790 (16)0.0399 (6)
C340.5646 (3)0.1055 (2)0.86429 (19)0.0566 (8)
H34A0.47070.11040.87300.068*
C350.6422 (4)0.0185 (2)0.8990 (2)0.0677 (9)
H35A0.6001−0.03300.93080.081*
C360.7771 (4)0.0106 (2)0.8860 (2)0.0683 (10)
H36A0.8284−0.04730.90910.082*
C370.9870 (4)0.0775 (3)0.8269 (2)0.0681 (10)
H37A1.03690.01900.85010.082*
C381.0529 (3)0.1503 (3)0.7835 (2)0.0718 (10)
H38A1.14600.14360.77980.086*
C390.9791 (3)0.2366 (2)0.74377 (19)0.0549 (8)
H39A1.02510.28660.71320.066*
C400.8424 (3)0.2495 (2)0.74856 (16)0.0406 (6)
C410.7661 (3)0.17662 (19)0.80045 (16)0.0416 (7)
C420.8443 (3)0.0873 (2)0.83827 (18)0.0523 (8)
C430.5196 (3)0.27347 (19)0.79374 (16)0.0364 (6)
C440.7856 (2)0.3351 (2)0.68661 (16)0.0380 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.0333 (2)0.0320 (2)0.0315 (2)−0.00393 (17)−0.00973 (16)−0.00581 (16)
Mn20.0315 (2)0.0347 (2)0.0302 (2)−0.00291 (17)−0.00903 (16)−0.00567 (16)
O10.0309 (9)0.0412 (11)0.0367 (9)−0.0018 (8)−0.0149 (8)−0.0085 (8)
O1W0.0375 (11)0.0660 (14)0.0461 (11)−0.0069 (10)−0.0108 (8)−0.0143 (10)
O20.0279 (10)0.0872 (16)0.0441 (10)0.0038 (10)−0.0082 (8)−0.0219 (10)
O2W0.1071 (17)0.0392 (12)0.0356 (10)−0.0111 (11)−0.0227 (11)−0.0040 (9)
O30.0370 (11)0.0511 (13)0.0691 (13)−0.0090 (9)−0.0165 (9)−0.0124 (10)
O3W0.0442 (11)0.0711 (14)0.0375 (10)0.0161 (10)−0.0086 (8)−0.0071 (10)
O40.0353 (9)0.0334 (10)0.0339 (9)0.0017 (7)−0.0099 (7)−0.0045 (7)
O4W0.0425 (11)0.0464 (12)0.0609 (12)−0.0088 (8)−0.0163 (9)−0.0144 (9)
O50.0408 (10)0.0348 (10)0.0376 (9)0.0003 (8)−0.0130 (8)−0.0099 (8)
O5W0.135 (2)0.0717 (17)0.0772 (16)−0.0367 (16)−0.0068 (15)−0.0169 (13)
O60.0444 (11)0.0498 (12)0.0548 (11)−0.0058 (9)−0.0165 (9)−0.0186 (9)
O6W0.0503 (12)0.0620 (14)0.0833 (15)−0.0197 (11)−0.0154 (11)−0.0184 (12)
O70.0491 (12)0.0523 (13)0.0646 (13)−0.0152 (10)−0.0221 (10)−0.0123 (10)
O80.0347 (10)0.0420 (11)0.0327 (9)−0.0029 (8)−0.0115 (7)−0.0117 (8)
N10.0365 (12)0.0349 (13)0.0365 (11)−0.0080 (10)−0.0066 (9)−0.0080 (10)
N20.0313 (12)0.0341 (12)0.0376 (11)−0.0053 (10)−0.0096 (9)−0.0049 (9)
N30.0363 (12)0.0364 (12)0.0306 (11)−0.0052 (10)−0.0102 (9)−0.0036 (9)
N40.0314 (12)0.0363 (13)0.0374 (11)−0.0041 (10)−0.0093 (9)−0.0016 (10)
C10.0496 (18)0.0409 (17)0.0514 (16)−0.0159 (14)−0.0083 (13)−0.0036 (13)
C20.0457 (19)0.062 (2)0.065 (2)−0.0248 (17)−0.0051 (15)−0.0090 (17)
C30.0321 (16)0.068 (2)0.076 (2)−0.0112 (16)−0.0107 (15)−0.0121 (18)
C40.0324 (16)0.0529 (19)0.0619 (18)−0.0046 (14)−0.0133 (13)−0.0071 (15)
C50.0307 (14)0.0386 (16)0.0334 (13)−0.0029 (12)−0.0065 (11)−0.0123 (12)
C60.0339 (14)0.0308 (15)0.0286 (12)−0.0035 (12)−0.0060 (10)−0.0098 (11)
C70.0376 (15)0.0410 (17)0.0476 (16)0.0038 (13)−0.0140 (12)−0.0088 (13)
C80.0563 (19)0.0295 (16)0.0531 (17)−0.0040 (14)−0.0163 (14)0.0007 (13)
C90.0524 (19)0.0409 (18)0.0580 (18)−0.0169 (15)−0.0138 (14)0.0028 (14)
C100.0364 (15)0.0404 (17)0.0557 (17)−0.0079 (13)−0.0124 (13)−0.0027 (14)
C110.0325 (14)0.0418 (16)0.0407 (14)−0.0018 (12)−0.0164 (11)−0.0110 (12)
C120.0413 (17)0.075 (2)0.0647 (19)−0.0169 (16)−0.0157 (14)−0.0275 (17)
C130.055 (2)0.081 (3)0.094 (3)−0.0157 (19)−0.0222 (19)−0.044 (2)
C140.058 (2)0.075 (2)0.071 (2)0.0076 (15)−0.0334 (18)−0.0450 (19)
C150.080 (2)0.064 (2)0.0386 (16)0.0142 (19)−0.0195 (16)−0.0222 (16)
C160.076 (2)0.061 (2)0.0347 (16)0.0105 (19)0.0034 (15)−0.0059 (15)
C170.0469 (17)0.0460 (18)0.0471 (16)−0.0014 (14)0.0010 (13)−0.0021 (14)
C180.0395 (15)0.0308 (15)0.0345 (13)0.0057 (12)−0.0110 (12)−0.0018 (11)
C190.0346 (14)0.0356 (15)0.0365 (13)0.0070 (12)−0.0161 (11)−0.0091 (11)
C200.0505 (17)0.0488 (17)0.0422 (15)0.0132 (12)−0.0207 (13)−0.0177 (14)
C210.0305 (15)0.0389 (15)0.0355 (13)−0.0080 (12)−0.0089 (11)−0.0060 (12)
C220.0330 (12)0.0320 (15)0.0359 (13)−0.0037 (10)−0.0074 (11)0.0010 (11)
C230.0430 (16)0.0453 (17)0.0382 (14)−0.0153 (13)−0.0091 (12)−0.0037 (12)
C240.0515 (18)0.0550 (19)0.0380 (15)−0.0127 (15)−0.0015 (13)−0.0041 (14)
C250.0591 (19)0.058 (2)0.0301 (14)−0.0049 (16)−0.0044 (13)−0.0104 (13)
C260.0567 (18)0.0458 (18)0.0395 (15)−0.0067 (15)−0.0176 (14)−0.0130 (13)
C270.0383 (14)0.0308 (14)0.0334 (13)−0.0007 (12)−0.0165 (11)−0.0028 (11)
C280.0347 (14)0.0318 (14)0.0399 (14)−0.0007 (12)−0.0165 (11)−0.0033 (12)
C290.0487 (18)0.0542 (19)0.0550 (17)−0.0127 (15)−0.0199 (14)−0.0109 (15)
C300.058 (2)0.055 (2)0.079 (2)−0.0227 (17)−0.0274 (17)−0.0102 (17)
C310.0350 (16)0.0527 (19)0.070 (2)−0.0142 (15)−0.0120 (14)0.0043 (16)
C320.0336 (15)0.0435 (17)0.0510 (16)−0.0032 (13)−0.0096 (13)−0.0022 (13)
C330.0509 (18)0.0347 (16)0.0338 (13)0.0002 (13)−0.0129 (12)−0.0107 (12)
C340.071 (2)0.0453 (19)0.0509 (17)−0.0074 (17)−0.0137 (15)−0.0077 (15)
C350.099 (3)0.039 (2)0.058 (2)−0.007 (2)−0.018 (2)−0.0017 (15)
C360.100 (3)0.045 (2)0.0519 (19)0.018 (2)−0.031 (2)−0.0111 (16)
C370.074 (3)0.066 (2)0.054 (2)0.033 (2)−0.0330 (18)−0.0194 (18)
C380.052 (2)0.096 (3)0.064 (2)0.020 (2)−0.0286 (17)−0.026 (2)
C390.0449 (18)0.068 (2)0.0556 (18)0.0027 (16)−0.0219 (14)−0.0202 (16)
C400.0414 (16)0.0465 (17)0.0355 (14)0.0057 (13)−0.0148 (12)−0.0186 (13)
C410.0542 (18)0.0390 (16)0.0328 (13)0.0074 (14)−0.0192 (12)−0.0153 (12)
C420.068 (2)0.0467 (19)0.0381 (15)0.0158 (16)−0.0225 (14)−0.0162 (14)
C430.0402 (16)0.0362 (16)0.0301 (13)−0.0055 (13)−0.0050 (11)−0.0057 (12)
C440.0320 (15)0.0464 (18)0.0366 (14)−0.0011 (13)−0.0074 (11)−0.0171 (13)

Geometric parameters (Å, °)

Mn1—O12.1422 (15)C10—H10A0.9300
Mn1—O2W2.1590 (18)C11—C121.359 (3)
Mn1—O8i2.1864 (15)C11—C191.432 (3)
Mn1—O1W2.1878 (17)C11—C211.511 (3)
Mn1—N22.264 (2)C12—C131.400 (4)
Mn1—N12.276 (2)C12—H12A0.9300
Mn2—O42.1614 (16)C13—C141.340 (4)
Mn2—O3W2.1749 (16)C13—H13A0.9300
Mn2—O52.1913 (17)C14—C201.402 (4)
Mn2—O4W2.2288 (16)C14—H14A0.9300
Mn2—N32.2533 (18)C15—C161.350 (4)
Mn2—N42.258 (2)C15—C201.411 (4)
O1—C211.269 (3)C15—H15A0.9300
O1W—H1WA0.8451C16—C171.403 (4)
O1W—H1WB0.8403C16—H16A0.9300
O2—C211.238 (3)C17—C181.374 (3)
O2W—H2WA0.8269C17—H17A0.9300
O2W—H2WB0.8319C18—C191.423 (3)
O3—C221.243 (3)C18—C221.507 (3)
O3W—H3WA0.8400C19—C201.432 (3)
O3W—H3WB0.8399C23—C241.375 (3)
O4—C221.270 (3)C23—H23A0.9300
O4W—H4WA0.8733C24—C251.363 (4)
O4W—H4WB0.8342C24—H24A0.9300
O5—C431.265 (3)C25—C261.367 (4)
O5W—H5WA0.9661C25—H25A0.9300
O5W—H5WB0.9411C26—C271.383 (3)
O6—C431.260 (3)C26—H26A0.9300
O6W—H6WA0.8364C27—C281.488 (3)
O6W—H6WB0.8096C28—C291.375 (3)
O7—C441.247 (3)C29—C301.377 (4)
O8—C441.273 (3)C29—H29A0.9300
O8—Mn1i2.1864 (15)C30—C311.362 (4)
N1—C11.341 (3)C30—H30A0.9300
N1—C51.347 (3)C31—C321.372 (4)
N2—C101.337 (3)C31—H31A0.9300
N2—C61.342 (3)C32—H32A0.9300
N3—C231.332 (3)C33—C341.373 (4)
N3—C271.343 (3)C33—C411.420 (4)
N4—C321.342 (3)C33—C431.509 (3)
N4—C281.342 (3)C34—C351.399 (4)
C1—C21.374 (4)C34—H34A0.9300
C1—H1A0.9300C35—C361.333 (4)
C2—C31.361 (4)C35—H35A0.9300
C2—H2A0.9300C36—C421.411 (4)
C3—C41.378 (4)C36—H36A0.9300
C3—H3A0.9300C37—C381.344 (5)
C4—C51.386 (3)C37—C421.412 (4)
C4—H4A0.9300C37—H37A0.9300
C5—C61.480 (3)C38—C391.405 (4)
C6—C71.375 (3)C38—H38A0.9300
C7—C81.378 (4)C39—C401.363 (4)
C7—H7A0.9300C39—H39A0.9300
C8—C91.360 (4)C40—C411.436 (4)
C8—H8A0.9300C40—C441.494 (4)
C9—C101.375 (4)C41—C421.443 (4)
C9—H9A0.9300
O1—Mn1—O2W83.03 (6)C14—C13—C12119.0 (3)
O1—Mn1—O8i161.96 (6)C14—C13—H13A120.5
O2W—Mn1—O8i80.01 (6)C12—C13—H13A120.5
O1—Mn1—O1W89.79 (6)C13—C14—C20121.4 (3)
O2W—Mn1—O1W97.14 (7)C13—C14—H14A119.3
O8i—Mn1—O1W86.29 (6)C20—C14—H14A119.3
O1—Mn1—N296.36 (7)C16—C15—C20121.2 (3)
O2W—Mn1—N2174.79 (7)C16—C15—H15A119.4
O8i—Mn1—N2101.08 (6)C20—C15—H15A119.4
O1W—Mn1—N288.02 (7)C15—C16—C17119.7 (3)
O1—Mn1—N198.63 (6)C15—C16—H16A120.1
O2W—Mn1—N1103.07 (8)C17—C16—H16A120.1
O8i—Mn1—N191.17 (6)C18—C17—C16121.3 (3)
O1W—Mn1—N1158.87 (8)C18—C17—H17A119.4
N2—Mn1—N171.87 (7)C16—C17—H17A119.4
O4—Mn2—O3W83.70 (6)C17—C18—C19120.6 (2)
O4—Mn2—O5165.69 (6)C17—C18—C22114.4 (2)
O3W—Mn2—O585.90 (6)C19—C18—C22124.8 (2)
O4—Mn2—O4W84.94 (6)C18—C19—C11125.8 (2)
O3W—Mn2—O4W100.87 (7)C18—C19—C20117.1 (2)
O5—Mn2—O4W87.41 (6)C11—C19—C20117.1 (2)
O4—Mn2—N395.56 (6)C14—C20—C15119.8 (3)
O3W—Mn2—N3167.88 (7)C14—C20—C19120.2 (3)
O5—Mn2—N396.66 (7)C15—C20—C19119.9 (3)
O4W—Mn2—N391.10 (7)O2—C21—O1125.6 (2)
O4—Mn2—N494.31 (7)O2—C21—C11118.1 (2)
O3W—Mn2—N495.66 (7)O1—C21—C11116.1 (2)
O5—Mn2—N496.47 (7)O3—C22—O4124.5 (2)
O4W—Mn2—N4163.26 (7)O3—C22—C18118.5 (2)
N3—Mn2—N472.30 (7)O4—C22—C18116.8 (2)
C21—O1—Mn1124.46 (15)N3—C23—C24123.3 (2)
Mn1—O1W—H1WA101.5N3—C23—H23A118.3
Mn1—O1W—H1WB122.4C24—C23—H23A118.3
H1WA—O1W—H1WB103.1C25—C24—C23118.4 (3)
Mn1—O2W—H2WA120.1C25—C24—H24A120.8
Mn1—O2W—H2WB126.4C23—C24—H24A120.8
H2WA—O2W—H2WB105.6C24—C25—C26119.1 (2)
Mn2—O3W—H3WA117.9C24—C25—H25A120.4
Mn2—O3W—H3WB100.3C26—C25—H25A120.4
H3WA—O3W—H3WB136.0C25—C26—C27120.0 (2)
C22—O4—Mn2136.17 (15)C25—C26—H26A120.0
Mn2—O4W—H4WA93.6C27—C26—H26A120.0
Mn2—O4W—H4WB121.8N3—C27—C26120.9 (2)
H4WA—O4W—H4WB102.4N3—C27—C28116.1 (2)
C43—O5—Mn2124.04 (16)C26—C27—C28123.0 (2)
H5WA—O5W—H5WB83.4N4—C28—C29121.7 (2)
H6WA—O6W—H6WB106.2N4—C28—C27115.7 (2)
C44—O8—Mn1i132.04 (14)C29—C28—C27122.6 (2)
C1—N1—C5117.9 (2)C28—C29—C30119.4 (3)
C1—N1—Mn1124.66 (18)C28—C29—H29A120.3
C5—N1—Mn1117.44 (15)C30—C29—H29A120.3
C10—N2—C6117.5 (2)C31—C30—C29119.1 (3)
C10—N2—Mn1124.08 (17)C31—C30—H30A120.4
C6—N2—Mn1118.38 (16)C29—C30—H30A120.4
C23—N3—C27118.2 (2)C30—C31—C32118.9 (3)
C23—N3—Mn2123.94 (16)C30—C31—H31A120.5
C27—N3—Mn2117.85 (15)C32—C31—H31A120.5
C32—N4—C28118.0 (2)N4—C32—C31122.8 (3)
C32—N4—Mn2124.01 (17)N4—C32—H32A118.6
C28—N4—Mn2117.84 (16)C31—C32—H32A118.6
N1—C1—C2123.2 (3)C34—C33—C41119.8 (3)
N1—C1—H1A118.4C34—C33—C43114.2 (3)
C2—C1—H1A118.4C41—C33—C43125.9 (2)
C3—C2—C1118.8 (3)C33—C34—C35122.4 (3)
C3—C2—H2A120.6C33—C34—H34A118.8
C1—C2—H2A120.6C35—C34—H34A118.8
C2—C3—C4119.4 (3)C36—C35—C34119.2 (3)
C2—C3—H3A120.3C36—C35—H35A120.4
C4—C3—H3A120.3C34—C35—H35A120.4
C3—C4—C5119.2 (3)C35—C36—C42122.0 (3)
C3—C4—H4A120.4C35—C36—H36A119.0
C5—C4—H4A120.4C42—C36—H36A119.0
N1—C5—C4121.6 (2)C38—C37—C42121.9 (3)
N1—C5—C6116.4 (2)C38—C37—H37A119.0
C4—C5—C6122.0 (2)C42—C37—H37A119.0
N2—C6—C7121.9 (2)C37—C38—C39119.0 (3)
N2—C6—C5115.8 (2)C37—C38—H38A120.5
C7—C6—C5122.3 (2)C39—C38—H38A120.5
C6—C7—C8119.7 (3)C40—C39—C38122.2 (3)
C6—C7—H7A120.2C40—C39—H39A118.9
C8—C7—H7A120.2C38—C39—H39A118.9
C9—C8—C7118.8 (3)C39—C40—C41120.5 (3)
C9—C8—H8A120.6C39—C40—C44115.5 (3)
C7—C8—H8A120.6C41—C40—C44123.4 (2)
C8—C9—C10118.8 (3)C33—C41—C40126.5 (2)
C8—C9—H9A120.6C33—C41—C42117.1 (3)
C10—C9—H9A120.6C40—C41—C42116.4 (3)
N2—C10—C9123.4 (3)C36—C42—C37120.8 (3)
N2—C10—H10A118.3C36—C42—C41119.5 (3)
C9—C10—H10A118.3C37—C42—C41119.7 (3)
C12—C11—C19119.3 (2)O6—C43—O5124.7 (2)
C12—C11—C21114.2 (2)O6—C43—C33116.8 (2)
C19—C11—C21126.2 (2)O5—C43—C33118.1 (2)
C11—C12—C13123.0 (3)O7—C44—O8123.1 (2)
C11—C12—H12A118.5O7—C44—C40119.8 (2)
C13—C12—H12A118.5O8—C44—C40117.0 (2)
O2W—Mn1—O1—C2164.86 (19)C17—C18—C19—C204.1 (4)
O8i—Mn1—O1—C2144.9 (3)C22—C18—C19—C20−169.9 (2)
O1W—Mn1—O1—C21−32.36 (19)C12—C11—C19—C18178.5 (3)
N2—Mn1—O1—C21−120.34 (19)C21—C11—C19—C184.3 (4)
N1—Mn1—O1—C21167.10 (19)C12—C11—C19—C20−0.7 (4)
O3W—Mn2—O4—C22168.7 (2)C21—C11—C19—C20−175.0 (2)
O5—Mn2—O4—C22125.1 (3)C13—C14—C20—C15−177.8 (3)
O4W—Mn2—O4—C2267.2 (2)C13—C14—C20—C190.0 (5)
N3—Mn2—O4—C22−23.4 (2)C16—C15—C20—C14175.1 (3)
N4—Mn2—O4—C22−96.1 (2)C16—C15—C20—C19−2.7 (4)
O4—Mn2—O5—C43−23.0 (4)C18—C19—C20—C14−178.3 (2)
O3W—Mn2—O5—C43−66.42 (18)C11—C19—C20—C141.0 (4)
O4W—Mn2—O5—C4334.68 (18)C18—C19—C20—C15−0.5 (4)
N3—Mn2—O5—C43125.48 (18)C11—C19—C20—C15178.8 (2)
N4—Mn2—O5—C43−161.66 (18)Mn1—O1—C21—O24.7 (4)
O1—Mn1—N1—C1−89.05 (19)Mn1—O1—C21—C11178.84 (15)
O2W—Mn1—N1—C1−4.3 (2)C12—C11—C21—O256.0 (3)
O8i—Mn1—N1—C175.76 (19)C19—C11—C21—O2−129.5 (3)
O1W—Mn1—N1—C1158.48 (19)C12—C11—C21—O1−118.6 (3)
N2—Mn1—N1—C1177.0 (2)C19—C11—C21—O155.8 (3)
O1—Mn1—N1—C593.41 (16)Mn2—O4—C22—O3−105.4 (3)
O2W—Mn1—N1—C5178.20 (15)Mn2—O4—C22—C1870.1 (3)
O8i—Mn1—N1—C5−101.78 (16)C17—C18—C22—O347.9 (3)
O1W—Mn1—N1—C5−19.1 (3)C19—C18—C22—O3−137.7 (3)
N2—Mn1—N1—C5−0.50 (15)C17—C18—C22—O4−127.8 (2)
O1—Mn1—N2—C1082.40 (19)C19—C18—C22—O446.5 (3)
O8i—Mn1—N2—C10−92.99 (19)C27—N3—C23—C24−0.1 (4)
O1W—Mn1—N2—C10−7.17 (19)Mn2—N3—C23—C24−177.8 (2)
N1—Mn1—N2—C10179.4 (2)N3—C23—C24—C25−0.6 (4)
O1—Mn1—N2—C6−95.01 (16)C23—C24—C25—C260.5 (4)
O8i—Mn1—N2—C689.60 (16)C24—C25—C26—C270.3 (4)
O1W—Mn1—N2—C6175.42 (16)C23—N3—C27—C261.0 (4)
N1—Mn1—N2—C62.01 (15)Mn2—N3—C27—C26178.81 (18)
O4—Mn2—N3—C2387.9 (2)C23—N3—C27—C28−179.7 (2)
O3W—Mn2—N3—C23173.8 (3)Mn2—N3—C27—C28−1.9 (3)
O5—Mn2—N3—C23−84.6 (2)C25—C26—C27—N3−1.1 (4)
O4W—Mn2—N3—C232.9 (2)C25—C26—C27—C28179.6 (2)
N4—Mn2—N3—C23−179.3 (2)C32—N4—C28—C290.2 (4)
O4—Mn2—N3—C27−89.76 (17)Mn2—N4—C28—C29−176.44 (19)
O3W—Mn2—N3—C27−3.9 (4)C32—N4—C28—C27−179.0 (2)
O5—Mn2—N3—C2797.70 (17)Mn2—N4—C28—C274.4 (3)
O4W—Mn2—N3—C27−174.78 (17)N3—C27—C28—N4−1.7 (3)
N4—Mn2—N3—C273.01 (16)C26—C27—C28—N4177.6 (2)
O4—Mn2—N4—C32−85.9 (2)N3—C27—C28—C29179.2 (2)
O3W—Mn2—N4—C32−1.8 (2)C26—C27—C28—C29−1.5 (4)
O5—Mn2—N4—C3284.7 (2)N4—C28—C29—C30−0.6 (4)
O4W—Mn2—N4—C32−172.7 (2)C27—C28—C29—C30178.5 (3)
N3—Mn2—N4—C32179.6 (2)C28—C29—C30—C310.1 (4)
O4—Mn2—N4—C2890.49 (17)C29—C30—C31—C320.7 (4)
O3W—Mn2—N4—C28174.57 (17)C28—N4—C32—C310.7 (4)
O5—Mn2—N4—C28−98.93 (17)Mn2—N4—C32—C31177.1 (2)
O4W—Mn2—N4—C283.7 (4)C30—C31—C32—N4−1.1 (4)
N3—Mn2—N4—C28−3.97 (16)C41—C33—C34—C352.7 (4)
C5—N1—C1—C2−0.4 (4)C43—C33—C34—C35−174.6 (2)
Mn1—N1—C1—C2−177.9 (2)C33—C34—C35—C36−0.7 (4)
N1—C1—C2—C3−0.6 (4)C34—C35—C36—C420.1 (5)
C1—C2—C3—C41.0 (4)C42—C37—C38—C39−3.7 (5)
C2—C3—C4—C5−0.5 (4)C37—C38—C39—C400.7 (4)
C1—N1—C5—C40.9 (3)C38—C39—C40—C414.3 (4)
Mn1—N1—C5—C4178.60 (18)C38—C39—C40—C44−167.2 (2)
C1—N1—C5—C6−178.6 (2)C34—C33—C41—C40176.1 (2)
Mn1—N1—C5—C6−0.9 (2)C43—C33—C41—C40−7.0 (4)
C3—C4—C5—N1−0.5 (4)C34—C33—C41—C42−3.8 (3)
C3—C4—C5—C6179.0 (2)C43—C33—C41—C42173.1 (2)
C10—N2—C6—C7−0.7 (3)C39—C40—C41—C33174.2 (2)
Mn1—N2—C6—C7176.86 (17)C44—C40—C41—C33−15.1 (4)
C10—N2—C6—C5179.3 (2)C39—C40—C41—C42−6.0 (3)
Mn1—N2—C6—C5−3.1 (2)C44—C40—C41—C42164.8 (2)
N1—C5—C6—N22.6 (3)C35—C36—C42—C37178.9 (3)
C4—C5—C6—N2−176.8 (2)C35—C36—C42—C41−1.4 (4)
N1—C5—C6—C7−177.4 (2)C38—C37—C42—C36−178.5 (3)
C4—C5—C6—C73.2 (3)C38—C37—C42—C411.7 (4)
N2—C6—C7—C80.5 (4)C33—C41—C42—C363.2 (3)
C5—C6—C7—C8−179.5 (2)C40—C41—C42—C36−176.7 (2)
C6—C7—C8—C9−0.1 (4)C33—C41—C42—C37−177.1 (2)
C7—C8—C9—C10−0.1 (4)C40—C41—C42—C373.1 (3)
C6—N2—C10—C90.6 (4)Mn2—O5—C43—O6−10.1 (3)
Mn1—N2—C10—C9−176.84 (19)Mn2—O5—C43—C33176.67 (15)
C8—C9—C10—N2−0.2 (4)C34—C33—C43—O6−48.6 (3)
C19—C11—C12—C13−0.6 (4)C41—C33—C43—O6134.4 (2)
C21—C11—C12—C13174.3 (3)C34—C33—C43—O5125.2 (2)
C11—C12—C13—C141.7 (5)C41—C33—C43—O5−51.8 (3)
C12—C13—C14—C20−1.3 (5)Mn1i—O8—C44—O7107.6 (3)
C20—C15—C16—C172.3 (5)Mn1i—O8—C44—C40−68.3 (3)
C15—C16—C17—C181.4 (5)C39—C40—C44—O7−41.9 (3)
C16—C17—C18—C19−4.7 (4)C41—C40—C44—O7146.9 (2)
C16—C17—C18—C22169.9 (2)C39—C40—C44—O8134.2 (2)
C17—C18—C19—C11−175.1 (2)C41—C40—C44—O8−37.0 (3)
C22—C18—C19—C1110.8 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O20.852.002.690 (2)139
O1W—H1WB···O6i0.842.012.776 (2)151
O2W—H2WA···O40.831.902.712 (2)166
O2W—H2WB···O5W0.831.902.716 (3)169
O3W—H3WA···O80.841.922.742 (2)167
O3W—H3WB···O2W0.842.243.083 (3)180
O4W—H4WA···O60.871.782.622 (2)161
O4W—H4WB···O6W0.832.032.853 (3)170
O5W—H5WA···O7i0.972.162.807 (3)123
O5W—H5WB···O6W0.942.072.930 (3)150
O6W—H6WA···O7ii0.841.992.798 (3)164
O6W—H6WB···O30.811.952.752 (3)171

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5168).

References

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