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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1677.
Published online 2010 November 27. doi:  10.1107/S1600536810045587
PMCID: PMC3011708

Poly[(μ3-biphenyl-3,4′-dicarboxyl­ato-κ4 O 3:O 3′:O 4′,O 4′′)(1H-imidazo[4,5-f][1,10]phenanthroline-κ2 N 7,N 8)manganese(II)]

Abstract

In the title compound, [Mn(C14H8O4)(C13H8N4)]n, the MnII atom is six-coordinated in a distorted octa­hedral geometry by four O atoms from three different carboxyl­ate groups and two N atoms from one imidazo[4,5-f][1,10]phenanthroline mol­ecule. The organic ligands link inorganic MnII nodes, forming a zigzag chain along the c axis.

Related literature

For the use of diphenic acid as an O-donor ligand in the design and synthesis of coordination polymers, see: Wang et al. (2006 [triangle]); Yin et al. (2005 [triangle]). The distortion of the diphenyl spacer about the central bond allows the carboxyl­ate ligand to link metal ions into helical chains or one dimensional chains, see: Guo et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1677-scheme1.jpg

Experimental

Crystal data

  • [Mn(C14H8O4)(C13H8N4)]
  • M r = 515.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1677-efi1.jpg
  • a = 8.0634 (13) Å
  • b = 11.705 (2) Å
  • c = 22.807 (4) Å
  • β = 94.307 (2)°
  • V = 2146.5 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.66 mm−1
  • T = 296 K
  • 0.30 × 0.25 × 0.15 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.915, T max = 0.949
  • 12211 measured reflections
  • 3997 independent reflections
  • 2211 reflections with I > 2σ(I)
  • R int = 0.079

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.107
  • S = 1.00
  • 3997 reflections
  • 325 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999) [triangle]; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045587/jh2224sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045587/jh2224Isup2.hkl

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

supplementary crystallographic information

Comment

Diphenic acid as O-donor ligand has received much more attention in the designed synthesis of coordination polymers (Wang, et al., 2006; Yin,et al., 2005). I select 3,4'-biphenyldicarboxylicacid as the ligand based on the following consideratons. First, the two functional carboxylate groups can adopt different coordination modes. Second, two phenyl rings are not coplanar with each other owing to the steric hindrance of carboxylate groups in coordinaton process. The distortion of diphenyl spacer about the central bond allows the carboxylate ligand to link metal ions into helical chains or one dimensional chains (Guo, et al., 2010).

The title compound,(I), was synthesized by the hydrothermal reaction of 3,4'-biphenyldicarboxylic acid with imidazo[4,5-f][1,10]phenanthroline and manganese chloride terahydrate. The central MnII exhibits an octahedral geometry with N2O4 coordination sphere from three carboxylate ligands and one imidazo[4,5-f][1,10]phenanthroline ligand. The carboxylate groups act as m3-ligand with one carboxylate group bridging two MnII ions in a bis-monodetate fashion, and the other carboxylate group bridging MnII in a bidentate chelating mode. The dihedral angle two phenyl rings in carboxylate ligand is 9.33°. The carboxylate ligands link MnII nodes to form one-dimensional zigzag chain along c axis.

Experimental

A mixture of MnCl2.4H2O (0.099 g, 0.5 mmol), 3,4'-biphenyldicarboxylic acid (0.121 g,0.5 mmol), NaOH (0.04 g, 1 mmol), imidazo[4,5-f][1,10]phenanthroline (0.110 g,0.5 mmol)and distillated water (15 ml) was heated to 433 K for 96 h in a 25 ml stainless steel reactor with a Teflon liner. Yellow block crystals were obtained with 52% yield on Mn basis.

Refinement

Hydrogen atoms were included in calculated positions and refined with fixed thermal parameters riding on their parent atoms with C—H distances in the range of 0.93–0.98 Å.

Figures

Fig. 1.
The coordination environments of manganese(II) atom. All hydrogen atoms are omitted for clarity.
Fig. 2.
View of the one-dimensional zigzag chain running along c axis in compound

Crystal data

[Mn(C14H8O4)(C13H8N4)]F(000) = 1052
Mr = 515.38Dx = 1.595 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
a = 8.0634 (13) ÅCell parameters from 1052 reflections
b = 11.705 (2) Åθ = 2.5–19.6°
c = 22.807 (4) ŵ = 0.66 mm1
β = 94.307 (2)°T = 296 K
V = 2146.5 (6) Å3Block, yellow
Z = 40.30 × 0.25 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer3997 independent reflections
Radiation source: fine-focus sealed tube2211 reflections with I > 2σ(I)
graphiteRint = 0.079
[var phi] and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −9→9
Tmin = 0.915, Tmax = 0.949k = −14→13
12211 measured reflectionsl = −27→27

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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.026P)2 + 0.6105P] where P = (Fo2 + 2Fc2)/3
3997 reflections(Δ/σ)max < 0.001
325 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.25 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
C10.3326 (5)−0.2910 (3)0.59868 (17)0.0397 (10)
C20.4198 (5)−0.2655 (3)0.54479 (16)0.0366 (10)
C30.5437 (5)−0.3374 (4)0.52782 (18)0.0544 (12)
H30.5755−0.40070.55070.065*
C40.6200 (6)−0.3150 (4)0.4769 (2)0.0653 (14)
H40.7027−0.36350.46530.078*
C50.5739 (5)−0.2205 (4)0.44316 (19)0.0583 (13)
H50.6266−0.20680.40890.070*
C60.4504 (5)−0.1452 (3)0.45896 (16)0.0384 (10)
C70.3743 (5)−0.1712 (3)0.51070 (15)0.0360 (9)
H70.2906−0.12350.52240.043*
C80.3964 (5)−0.0463 (3)0.42123 (16)0.0359 (10)
C90.4790 (5)−0.0157 (3)0.37261 (17)0.0454 (11)
H90.5760−0.05430.36510.054*
C100.4217 (5)0.0706 (3)0.33468 (17)0.0445 (11)
H100.47950.08870.30210.053*
C110.2787 (5)0.1298 (3)0.34526 (16)0.0348 (10)
C120.2034 (5)0.2153 (3)0.30153 (18)0.0395 (10)
C130.2002 (5)0.1057 (3)0.39553 (17)0.0455 (11)
H130.10780.14810.40440.055*
C140.2582 (5)0.0185 (3)0.43296 (17)0.0479 (12)
H140.20350.00320.46660.058*
C150.3314 (5)0.4924 (4)0.29153 (17)0.0449 (11)
H150.36560.42210.30720.054*
C160.3820 (5)0.5911 (4)0.32141 (17)0.0499 (12)
H160.44830.58650.35650.060*
C170.3340 (5)0.6951 (4)0.29906 (17)0.0478 (12)
H170.36540.76170.31910.057*
C180.2367 (5)0.7004 (3)0.24547 (16)0.0335 (9)
C190.1832 (5)0.8018 (3)0.21576 (19)0.0428 (11)
C200.1350 (6)0.9765 (4)0.1863 (3)0.0705 (15)
H200.13501.05600.18550.085*
C210.0931 (5)0.8014 (4)0.16250 (19)0.0437 (11)
C220.0414 (5)0.6983 (3)0.13349 (17)0.0388 (10)
C23−0.0542 (5)0.6908 (4)0.08015 (18)0.0535 (12)
H23−0.08760.75670.05980.064*
C24−0.0983 (5)0.5857 (4)0.05792 (18)0.0519 (12)
H24−0.16260.57930.02250.062*
C25−0.0458 (5)0.4885 (4)0.08908 (17)0.0464 (11)
H25−0.07800.41740.07390.056*
C260.0901 (5)0.5956 (3)0.16214 (16)0.0336 (10)
C270.1912 (4)0.5964 (3)0.21789 (16)0.0315 (9)
Mn10.15985 (8)0.33674 (5)0.18767 (2)0.03702 (19)
N10.2089 (4)0.9153 (3)0.23044 (17)0.0551 (10)
H10.26180.94140.26170.066*
N20.0616 (5)0.9125 (3)0.14389 (18)0.0655 (12)
N30.0475 (4)0.4922 (3)0.13919 (13)0.0372 (8)
N40.2358 (4)0.4944 (3)0.24136 (13)0.0358 (8)
O10.3863 (3)−0.3680 (2)0.63325 (12)0.0545 (8)
O20.2030 (4)−0.2362 (2)0.60829 (12)0.0541 (8)
O30.2624 (3)0.2201 (2)0.25189 (11)0.0486 (8)
O4−0.0869 (4)0.2767 (2)0.18362 (12)0.0510 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.045 (3)0.038 (3)0.036 (2)−0.001 (2)−0.004 (2)0.005 (2)
C20.040 (3)0.036 (2)0.033 (2)−0.002 (2)−0.003 (2)0.0031 (19)
C30.054 (3)0.058 (3)0.052 (3)0.006 (3)0.009 (2)0.017 (2)
C40.062 (3)0.070 (4)0.067 (3)0.030 (3)0.023 (3)0.020 (3)
C50.061 (3)0.069 (3)0.046 (3)0.014 (3)0.015 (2)0.022 (3)
C60.034 (2)0.042 (3)0.039 (2)−0.002 (2)−0.0045 (19)0.000 (2)
C70.036 (2)0.037 (2)0.034 (2)0.003 (2)−0.0036 (18)0.000 (2)
C80.038 (3)0.037 (2)0.032 (2)−0.001 (2)−0.006 (2)−0.0001 (18)
C90.054 (3)0.045 (3)0.039 (2)0.008 (2)0.009 (2)0.007 (2)
C100.054 (3)0.045 (3)0.036 (2)0.003 (2)0.009 (2)0.003 (2)
C110.040 (3)0.032 (2)0.031 (2)0.001 (2)−0.0053 (19)0.0021 (17)
C120.048 (3)0.030 (2)0.040 (3)−0.006 (2)0.003 (2)−0.002 (2)
C130.044 (3)0.042 (3)0.050 (3)0.009 (2)0.007 (2)0.006 (2)
C140.047 (3)0.054 (3)0.044 (3)0.007 (2)0.011 (2)0.018 (2)
C150.048 (3)0.047 (3)0.040 (3)0.001 (2)−0.004 (2)−0.001 (2)
C160.054 (3)0.058 (3)0.036 (3)−0.001 (3)−0.009 (2)0.000 (2)
C170.048 (3)0.046 (3)0.048 (3)−0.009 (2)0.000 (2)−0.013 (2)
C180.032 (2)0.029 (2)0.039 (2)−0.0037 (19)0.0022 (19)−0.0025 (19)
C190.044 (3)0.031 (3)0.054 (3)0.002 (2)0.009 (2)−0.005 (2)
C200.076 (4)0.032 (3)0.103 (4)0.004 (3)0.005 (3)0.000 (3)
C210.048 (3)0.033 (3)0.050 (3)0.003 (2)0.006 (2)0.006 (2)
C220.038 (3)0.038 (3)0.040 (2)0.006 (2)0.005 (2)0.006 (2)
C230.057 (3)0.052 (3)0.050 (3)0.007 (2)−0.007 (2)0.012 (2)
C240.055 (3)0.059 (3)0.039 (3)0.001 (3)−0.017 (2)0.005 (2)
C250.057 (3)0.042 (3)0.038 (3)−0.005 (2)−0.012 (2)−0.004 (2)
C260.032 (2)0.029 (2)0.039 (2)−0.002 (2)0.0015 (19)−0.0043 (19)
C270.032 (2)0.030 (2)0.033 (2)0.000 (2)0.0014 (18)0.0004 (19)
Mn10.0488 (4)0.0288 (3)0.0331 (3)−0.0021 (3)0.0009 (3)0.0000 (3)
N10.063 (3)0.033 (2)0.068 (3)−0.005 (2)0.002 (2)−0.011 (2)
N20.077 (3)0.033 (2)0.084 (3)0.004 (2)−0.008 (2)0.006 (2)
N30.041 (2)0.035 (2)0.035 (2)−0.0062 (17)−0.0028 (16)0.0010 (16)
N40.039 (2)0.035 (2)0.0322 (19)0.0018 (17)−0.0042 (16)0.0014 (16)
O10.055 (2)0.061 (2)0.0474 (18)0.0062 (16)0.0023 (15)0.0234 (16)
O20.057 (2)0.053 (2)0.0532 (19)0.0139 (17)0.0165 (16)0.0146 (15)
O30.064 (2)0.0449 (18)0.0371 (16)0.0085 (15)0.0060 (15)0.0079 (14)
O40.051 (2)0.0479 (19)0.0544 (19)−0.0143 (16)0.0055 (15)−0.0037 (15)

Geometric parameters (Å, °)

C1—O11.253 (4)C17—H170.9300
C1—O21.259 (4)C18—C271.406 (5)
C1—C21.491 (5)C18—C191.417 (5)
C2—C31.384 (5)C19—C211.368 (5)
C2—C71.385 (5)C19—N11.382 (5)
C3—C41.379 (5)C20—N21.328 (5)
C3—H30.9300C20—N11.338 (5)
C4—C51.382 (5)C20—H200.9300
C4—H40.9300C21—N21.386 (5)
C5—C61.398 (5)C21—C221.424 (5)
C5—H50.9300C22—C231.393 (5)
C6—C71.404 (5)C22—C261.410 (5)
C6—C81.487 (5)C23—C241.367 (5)
C7—H70.9300C23—H230.9300
C8—C91.383 (5)C24—C251.391 (5)
C8—C141.391 (5)C24—H240.9300
C9—C101.387 (5)C25—N31.321 (4)
C9—H90.9300C25—H250.9300
C10—C111.382 (5)C26—N31.352 (4)
C10—H100.9300C26—C271.458 (5)
C11—C131.380 (5)C27—N41.347 (4)
C11—C121.508 (5)Mn1—O42.106 (3)
C12—O4i1.250 (4)Mn1—O32.124 (3)
C12—O31.262 (4)Mn1—O2ii2.208 (3)
C13—C141.388 (5)Mn1—N42.273 (3)
C13—H130.9300Mn1—N32.281 (3)
C14—H140.9300Mn1—O1ii2.313 (3)
C15—N41.331 (4)Mn1—C1ii2.602 (4)
C15—C161.387 (5)N1—H10.8600
C15—H150.9300O1—Mn1iii2.313 (3)
C16—C171.364 (5)O2—Mn1iii2.208 (3)
C16—H160.9300O4—C12i1.250 (4)
C17—C181.403 (5)
O1—C1—O2120.6 (4)N2—C20—N1113.2 (4)
O1—C1—C2120.0 (4)N2—C20—H20123.4
O2—C1—C2119.4 (4)N1—C20—H20123.4
O1—C1—Mn1iii62.7 (2)C19—C21—N2110.0 (4)
O2—C1—Mn1iii57.9 (2)C19—C21—C22122.2 (4)
C2—C1—Mn1iii175.7 (3)N2—C21—C22127.8 (4)
C3—C2—C7119.6 (4)C23—C22—C26117.9 (4)
C3—C2—C1120.3 (4)C23—C22—C21125.6 (4)
C7—C2—C1120.1 (4)C26—C22—C21116.5 (4)
C4—C3—C2119.8 (4)C24—C23—C22119.5 (4)
C4—C3—H3120.1C24—C23—H23120.3
C2—C3—H3120.1C22—C23—H23120.3
C3—C4—C5120.2 (4)C23—C24—C25119.1 (4)
C3—C4—H4119.9C23—C24—H24120.5
C5—C4—H4119.9C25—C24—H24120.5
C4—C5—C6121.9 (4)N3—C25—C24123.2 (4)
C4—C5—H5119.1N3—C25—H25118.4
C6—C5—H5119.1C24—C25—H25118.4
C5—C6—C7116.4 (4)N3—C26—C22122.0 (3)
C5—C6—C8121.7 (4)N3—C26—C27116.9 (4)
C7—C6—C8121.8 (4)C22—C26—C27121.1 (4)
C2—C7—C6122.1 (4)N4—C27—C18122.5 (3)
C2—C7—H7119.0N4—C27—C26117.1 (3)
C6—C7—H7119.0C18—C27—C26120.4 (4)
C9—C8—C14117.0 (4)O4—Mn1—O397.67 (11)
C9—C8—C6121.8 (4)O4—Mn1—O2ii89.59 (11)
C14—C8—C6121.2 (4)O3—Mn1—O2ii98.36 (11)
C8—C9—C10122.1 (4)O4—Mn1—N4120.65 (11)
C8—C9—H9119.0O3—Mn1—N494.32 (11)
C10—C9—H9119.0O2ii—Mn1—N4145.23 (11)
C11—C10—C9120.0 (4)O4—Mn1—N384.57 (11)
C11—C10—H10120.0O3—Mn1—N3165.21 (11)
C9—C10—H10120.0O2ii—Mn1—N396.26 (11)
C13—C11—C10118.9 (4)N4—Mn1—N372.22 (11)
C13—C11—C12119.9 (4)O4—Mn1—O1ii144.17 (10)
C10—C11—C12121.1 (4)O3—Mn1—O1ii100.92 (10)
O4i—C12—O3124.0 (4)O2ii—Mn1—O1ii57.65 (10)
O4i—C12—C11118.4 (4)N4—Mn1—O1ii88.24 (10)
O3—C12—C11117.6 (4)N3—Mn1—O1ii85.10 (11)
C11—C13—C14120.5 (4)O4—Mn1—C1ii117.17 (12)
C11—C13—H13119.8O3—Mn1—C1ii101.66 (11)
C14—C13—H13119.8O2ii—Mn1—C1ii28.90 (10)
C13—C14—C8121.4 (4)N4—Mn1—C1ii116.67 (12)
C13—C14—H14119.3N3—Mn1—C1ii90.13 (11)
C8—C14—H14119.3O1ii—Mn1—C1ii28.77 (10)
N4—C15—C16122.5 (4)C20—N1—C19106.4 (4)
N4—C15—H15118.7C20—N1—H1126.8
C16—C15—H15118.7C19—N1—H1126.8
C17—C16—C15119.7 (4)C20—N2—C21104.2 (4)
C17—C16—H16120.2C25—N3—C26118.4 (3)
C15—C16—H16120.2C25—N3—Mn1124.9 (3)
C16—C17—C18119.3 (4)C26—N3—Mn1116.5 (2)
C16—C17—H17120.3C15—N4—C27118.5 (3)
C18—C17—H17120.3C15—N4—Mn1124.3 (3)
C17—C18—C27117.5 (4)C27—N4—Mn1116.9 (2)
C17—C18—C19125.7 (4)C1—O1—Mn1iii88.5 (3)
C27—C18—C19116.8 (4)C1—O2—Mn1iii93.2 (2)
C21—C19—N1106.2 (4)C12—O3—Mn1119.6 (3)
C21—C19—C18123.0 (4)C12i—O4—Mn1155.1 (3)
N1—C19—C18130.9 (4)
O1—C1—C2—C310.1 (6)C22—C26—C27—N4−178.2 (3)
O2—C1—C2—C3−168.5 (4)N3—C26—C27—C18−178.2 (3)
Mn1iii—C1—C2—C3−118 (4)C22—C26—C27—C182.6 (6)
O1—C1—C2—C7−171.5 (4)N2—C20—N1—C190.5 (6)
O2—C1—C2—C710.0 (6)C21—C19—N1—C20−0.1 (5)
Mn1iii—C1—C2—C760 (4)C18—C19—N1—C20178.4 (4)
C7—C2—C3—C4−0.5 (6)N1—C20—N2—C21−0.6 (6)
C1—C2—C3—C4178.0 (4)C19—C21—N2—C200.5 (5)
C2—C3—C4—C50.5 (7)C22—C21—N2—C20179.6 (4)
C3—C4—C5—C60.1 (7)C24—C25—N3—C261.9 (6)
C4—C5—C6—C7−0.7 (6)C24—C25—N3—Mn1−173.4 (3)
C4—C5—C6—C8−177.5 (4)C22—C26—N3—C25−1.6 (6)
C3—C2—C7—C6−0.2 (6)C27—C26—N3—C25179.2 (3)
C1—C2—C7—C6−178.6 (3)C22—C26—N3—Mn1174.1 (3)
C5—C6—C7—C20.7 (5)C27—C26—N3—Mn1−5.1 (4)
C8—C6—C7—C2177.5 (3)O4—Mn1—N3—C25−54.9 (3)
C5—C6—C8—C9−8.1 (6)O3—Mn1—N3—C25−154.4 (4)
C7—C6—C8—C9175.2 (4)O2ii—Mn1—N3—C2534.1 (3)
C5—C6—C8—C14170.9 (4)N4—Mn1—N3—C25−179.5 (3)
C7—C6—C8—C14−5.8 (6)O1ii—Mn1—N3—C2590.8 (3)
C14—C8—C9—C10−4.2 (6)C1ii—Mn1—N3—C2562.4 (3)
C6—C8—C9—C10174.9 (4)O4—Mn1—N3—C26129.7 (3)
C8—C9—C10—C110.6 (6)O3—Mn1—N3—C2630.2 (6)
C9—C10—C11—C133.5 (6)O2ii—Mn1—N3—C26−141.3 (3)
C9—C10—C11—C12−173.4 (3)N4—Mn1—N3—C265.1 (3)
C13—C11—C12—O4i12.0 (5)O1ii—Mn1—N3—C26−84.6 (3)
C10—C11—C12—O4i−171.1 (4)C1ii—Mn1—N3—C26−113.0 (3)
C13—C11—C12—O3−167.9 (4)C16—C15—N4—C272.2 (6)
C10—C11—C12—O39.0 (5)C16—C15—N4—Mn1176.6 (3)
C10—C11—C13—C14−3.9 (6)C18—C27—N4—C15−2.4 (6)
C12—C11—C13—C14173.0 (4)C26—C27—N4—C15178.4 (3)
C11—C13—C14—C80.3 (6)C18—C27—N4—Mn1−177.2 (3)
C9—C8—C14—C133.7 (6)C26—C27—N4—Mn13.6 (4)
C6—C8—C14—C13−175.3 (4)O4—Mn1—N4—C15108.8 (3)
N4—C15—C16—C17−0.4 (7)O3—Mn1—N4—C157.2 (3)
C15—C16—C17—C18−1.3 (6)O2ii—Mn1—N4—C15−104.2 (3)
C16—C17—C18—C271.1 (6)N3—Mn1—N4—C15−179.0 (3)
C16—C17—C18—C19−177.3 (4)O1ii—Mn1—N4—C15−93.6 (3)
C17—C18—C19—C21177.7 (4)C1ii—Mn1—N4—C15−98.1 (3)
C27—C18—C19—C21−0.7 (6)O4—Mn1—N4—C27−76.8 (3)
C17—C18—C19—N1−0.6 (7)O3—Mn1—N4—C27−178.3 (3)
C27—C18—C19—N1−179.0 (4)O2ii—Mn1—N4—C2770.3 (3)
N1—C19—C21—N2−0.2 (5)N3—Mn1—N4—C27−4.6 (3)
C18—C19—C21—N2−178.9 (4)O1ii—Mn1—N4—C2780.9 (3)
N1—C19—C21—C22−179.4 (4)C1ii—Mn1—N4—C2776.3 (3)
C18—C19—C21—C222.0 (7)O2—C1—O1—Mn1iii2.3 (4)
C19—C21—C22—C23178.2 (4)C2—C1—O1—Mn1iii−176.2 (3)
N2—C21—C22—C23−0.8 (7)O1—C1—O2—Mn1iii−2.4 (4)
C19—C21—C22—C26−0.9 (6)C2—C1—O2—Mn1iii176.1 (3)
N2—C21—C22—C26−179.9 (4)O4i—C12—O3—Mn1−0.8 (5)
C26—C22—C23—C240.6 (6)C11—C12—O3—Mn1179.1 (2)
C21—C22—C23—C24−178.4 (4)O4—Mn1—O3—C12−57.7 (3)
C22—C23—C24—C25−0.3 (7)O2ii—Mn1—O3—C12−148.5 (3)
C23—C24—C25—N3−1.0 (7)N4—Mn1—O3—C1264.0 (3)
C23—C22—C26—N30.4 (6)N3—Mn1—O3—C1240.1 (6)
C21—C22—C26—N3179.5 (3)O1ii—Mn1—O3—C12153.0 (3)
C23—C22—C26—C27179.6 (4)C1ii—Mn1—O3—C12−177.6 (3)
C21—C22—C26—C27−1.3 (6)O3—Mn1—O4—C12i4.0 (7)
C17—C18—C27—N40.8 (6)O2ii—Mn1—O4—C12i102.4 (6)
C19—C18—C27—N4179.3 (3)N4—Mn1—O4—C12i−95.7 (7)
C17—C18—C27—C26179.9 (3)N3—Mn1—O4—C12i−161.3 (7)
C19—C18—C27—C26−1.5 (5)O1ii—Mn1—O4—C12i124.8 (6)
N3—C26—C27—N41.0 (5)C1ii—Mn1—O4—C12i111.3 (6)

Symmetry codes: (i) −x, y, −z+1/2; (ii) x, −y, z−1/2; (iii) x, −y, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2224).

References

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