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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1543.
Published online 2009 November 7. doi:  10.1107/S1600536809046388
PMCID: PMC2971822

Poly[aqua­bis(μ4-naphthalene-1,4-di­carboxyl­ato)(1,10-phenanthroline-5,6-dione)dimanganese(II)]

Abstract

The three-dimensional coordination polymer, [Mn2(C12H6O4)2(C12H6N2O2)(H2O)]n, features a water-coord­inated MnII ion and an N-heterocycle-chelated MnII ion, both in six-coordinate octa­hedral geometries. Of the two rigid dianions, one is bonded to four MnII ions, with each of the O atoms being connected to a different metal ion. The other dianion uses one carboxyl­ate group to chelate to one MnII ion and its other carboxyl­ate group to bind to two MnII ions.

Related literature

For similiar manganese naphthalene-1,4-dicarboxyl­ate polymers, see: Boeckmann et al. (2009 [triangle]); Li et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1543-scheme1.jpg

Experimental

Crystal data

  • [Mn2(C12H6O4)2(C12H6N2O2)(H2O)]
  • M r = 766.42
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1543-efi1.jpg
  • a = 8.4393 (8) Å
  • b = 19.2477 (18) Å
  • c = 19.2504 (19) Å
  • β = 101.781 (1)°
  • V = 3061.1 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.90 mm−1
  • T = 293 K
  • 0.27 × 0.26 × 0.20 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.794, T max = 0.841
  • 16986 measured reflections
  • 6015 independent reflections
  • 4853 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.096
  • S = 1.03
  • 6015 reflections
  • 466 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046388/ci2963sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046388/ci2963Isup2.hkl

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

Acknowledgments

The authors thank Tianjin Agricultural University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Manganese dichloride tetrahydrate (0.5 mmol, 0.099 g), naphthalene-1,4-dicarboxylic acid (0.5 mmol, 0.108 g), phenanthrene-9,10-dione (0.5 mmol, 0.104 g) and water (12 ml) were heated in a Teflon-lined, stainless-steel Parr bomb at 433 K for 3 days. Yellow crystals were isolated from the cool bomb in 40% yield.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C-H = 0.93 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The water H atoms were located in a difference Fourier map, and were refined with distance restraints of O–H = 0.85 (1) Å and H···H 1.39 (1) Å; their Uiso values were set to 1.5Ueq(O).

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of a part of the polymeric three-dimensional structure of Mn2(H2O)(C12H6O4)2(C12H6N2O2) at the 50% probability level; H atoms are drawn as spheres of arbitrary radius. Symmetry codes are given in Table 1.

Crystal data

[Mn2(C12H6O4)2(C12H6N2O2)(H2O)]F(000) = 1552
Mr = 766.42Dx = 1.663 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5446 reflections
a = 8.4393 (8) Åθ = 2.1–25.7°
b = 19.2477 (18) ŵ = 0.90 mm1
c = 19.2504 (19) ÅT = 293 K
β = 101.781 (1)°Block, yellow
V = 3061.1 (5) Å30.27 × 0.26 × 0.20 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer6015 independent reflections
Radiation source: fine-focus sealed tube4853 reflections with I > 2σ(I)
graphiteRint = 0.025
[var phi] and ω scansθmax = 26.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.794, Tmax = 0.841k = −15→23
16986 measured reflectionsl = −23→22

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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0581P)2 + 0.1115P] where P = (Fo2 + 2Fc2)/3
6015 reflections(Δ/σ)max = 0.001
466 parametersΔρmax = 0.40 e Å3
3 restraintsΔρmin = −0.24 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Mn10.67563 (4)0.723418 (17)0.635261 (16)0.02973 (10)
Mn20.32185 (4)0.688473 (16)0.694983 (16)0.02825 (10)
O10.49411 (18)0.71363 (9)0.54284 (8)0.0435 (4)
O20.2654 (2)0.69971 (10)0.58282 (8)0.0491 (4)
O30.09036 (18)0.76369 (9)0.19849 (8)0.0381 (4)
O4−0.14651 (18)0.76639 (9)0.23115 (8)0.0448 (4)
O50.55827 (18)0.64436 (7)0.68920 (9)0.0371 (4)
O60.7185 (2)0.59280 (10)0.63001 (11)0.0591 (5)
O70.4054 (2)0.32857 (10)0.84788 (10)0.0574 (5)
O80.5400 (2)0.27848 (8)0.77449 (11)0.0557 (5)
O90.0460 (3)0.40503 (13)0.83873 (16)0.1069 (9)
O100.2619 (3)0.45832 (15)0.95212 (15)0.1063 (10)
O1W0.8607 (2)0.75106 (16)0.57777 (10)0.0787 (7)
H1W10.949 (3)0.754 (2)0.6082 (16)0.118*
H1W20.851 (4)0.7853 (14)0.5499 (17)0.118*
N10.1895 (2)0.58539 (10)0.69258 (11)0.0396 (5)
N20.3748 (2)0.64538 (10)0.80699 (10)0.0356 (4)
C10.3440 (3)0.71125 (12)0.53511 (11)0.0334 (5)
C20.2493 (2)0.72461 (11)0.46106 (11)0.0306 (5)
C30.2775 (3)0.68379 (11)0.40590 (11)0.0328 (5)
H30.35020.64700.41510.039*
C40.1973 (2)0.69744 (11)0.33599 (11)0.0303 (5)
H40.21980.67030.29930.036*
C50.0864 (2)0.74994 (12)0.32073 (10)0.0291 (5)
C60.0551 (2)0.79415 (12)0.37652 (11)0.0312 (5)
C70.1407 (2)0.78174 (11)0.44707 (11)0.0310 (5)
C80.1222 (3)0.82974 (13)0.50106 (12)0.0406 (6)
H80.17850.82250.54730.049*
C90.0237 (3)0.88607 (14)0.48629 (14)0.0512 (7)
H90.01490.91740.52210.061*
C10−0.0644 (3)0.89695 (15)0.41734 (14)0.0543 (7)
H10−0.13360.93490.40790.065*
C11−0.0502 (3)0.85250 (13)0.36358 (13)0.0434 (6)
H11−0.10990.86050.31810.052*
C120.0036 (3)0.76148 (11)0.24480 (11)0.0303 (5)
C130.6211 (3)0.58948 (11)0.66943 (12)0.0335 (5)
C140.5764 (3)0.52226 (11)0.69999 (12)0.0352 (5)
C150.6256 (3)0.51188 (12)0.77124 (13)0.0437 (6)
H150.68300.54670.79900.052*
C160.5917 (3)0.44982 (12)0.80367 (13)0.0410 (6)
H160.63030.44330.85200.049*
C170.5020 (3)0.39879 (11)0.76437 (12)0.0341 (5)
C180.4411 (3)0.40882 (11)0.69041 (12)0.0342 (5)
C190.4819 (3)0.47085 (11)0.65730 (12)0.0347 (5)
C200.4218 (3)0.47993 (14)0.58366 (13)0.0462 (6)
H200.44740.52010.56140.055*
C210.3261 (3)0.43017 (15)0.54474 (14)0.0551 (7)
H210.29030.43610.49610.066*
C220.2825 (3)0.37081 (15)0.57776 (15)0.0556 (7)
H220.21500.33810.55100.067*
C230.3369 (3)0.35979 (13)0.64828 (14)0.0461 (6)
H230.30580.31990.66930.055*
C240.4799 (3)0.33048 (12)0.79864 (13)0.0393 (5)
C250.0982 (3)0.55711 (14)0.63501 (15)0.0518 (7)
H250.08970.58000.59190.062*
C260.0150 (3)0.49487 (16)0.63629 (19)0.0671 (9)
H26−0.04660.47620.59490.081*
C270.0261 (4)0.46209 (15)0.6996 (2)0.0687 (9)
H27−0.02830.42040.70190.082*
C280.1182 (3)0.49066 (13)0.76087 (17)0.0523 (7)
C290.1999 (3)0.55246 (11)0.75504 (13)0.0383 (5)
C300.1294 (4)0.45708 (16)0.8302 (2)0.0719 (10)
C310.2429 (3)0.48801 (17)0.89331 (19)0.0677 (9)
C320.3262 (3)0.55354 (14)0.88447 (15)0.0497 (7)
C330.3028 (3)0.58499 (12)0.81738 (13)0.0377 (5)
C340.4268 (4)0.58562 (17)0.94055 (15)0.0600 (8)
H340.44240.56630.98570.072*
C350.5043 (3)0.64632 (16)0.92973 (14)0.0558 (7)
H350.57500.66790.96680.067*
C360.4743 (3)0.67442 (13)0.86218 (13)0.0436 (6)
H360.52610.71560.85480.052*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.02579 (17)0.0373 (2)0.02387 (18)−0.00187 (13)−0.00003 (13)0.00353 (13)
Mn20.02932 (18)0.02970 (19)0.02565 (18)−0.00156 (13)0.00545 (13)0.00262 (13)
O10.0295 (8)0.0699 (12)0.0270 (9)0.0000 (8)−0.0040 (7)0.0044 (8)
O20.0406 (9)0.0801 (13)0.0252 (9)0.0001 (9)0.0033 (7)0.0107 (8)
O30.0312 (8)0.0585 (11)0.0239 (8)−0.0072 (7)0.0039 (6)0.0004 (7)
O40.0277 (8)0.0786 (13)0.0251 (8)0.0072 (8)−0.0019 (6)0.0002 (8)
O50.0374 (8)0.0267 (8)0.0477 (10)0.0047 (6)0.0099 (7)0.0071 (7)
O60.0663 (12)0.0533 (12)0.0682 (13)0.0105 (9)0.0383 (11)0.0109 (9)
O70.0712 (13)0.0504 (11)0.0552 (12)−0.0088 (9)0.0237 (10)0.0068 (9)
O80.0668 (12)0.0262 (9)0.0721 (13)0.0113 (8)0.0099 (10)0.0051 (8)
O90.114 (2)0.0741 (17)0.139 (3)−0.0251 (15)0.0409 (19)0.0406 (16)
O100.0751 (16)0.128 (2)0.116 (2)0.0035 (15)0.0201 (15)0.0892 (19)
O1W0.0413 (11)0.160 (2)0.0328 (11)−0.0267 (13)0.0040 (9)0.0165 (12)
N10.0353 (10)0.0389 (11)0.0448 (12)−0.0035 (8)0.0086 (9)−0.0023 (9)
N20.0357 (10)0.0387 (11)0.0330 (11)0.0031 (8)0.0083 (8)0.0026 (8)
C10.0356 (12)0.0398 (13)0.0233 (11)0.0000 (9)0.0026 (9)0.0007 (9)
C20.0242 (10)0.0420 (13)0.0235 (11)−0.0037 (9)−0.0001 (8)0.0032 (9)
C30.0305 (11)0.0364 (13)0.0293 (12)0.0020 (9)0.0007 (9)0.0014 (9)
C40.0304 (11)0.0338 (12)0.0252 (11)−0.0024 (9)0.0020 (9)−0.0028 (9)
C50.0248 (10)0.0380 (12)0.0226 (11)−0.0055 (9)0.0001 (8)0.0018 (9)
C60.0232 (10)0.0442 (13)0.0258 (11)0.0001 (9)0.0037 (8)0.0008 (9)
C70.0240 (10)0.0448 (14)0.0236 (11)−0.0022 (9)0.0038 (8)0.0021 (9)
C80.0403 (13)0.0570 (16)0.0241 (12)0.0035 (11)0.0055 (10)−0.0014 (10)
C90.0518 (15)0.0654 (18)0.0377 (15)0.0130 (13)0.0122 (12)−0.0118 (12)
C100.0486 (15)0.0658 (19)0.0469 (16)0.0253 (13)0.0062 (12)−0.0052 (13)
C110.0372 (12)0.0580 (17)0.0318 (13)0.0132 (11)−0.0002 (10)0.0000 (11)
C120.0310 (11)0.0355 (12)0.0219 (11)−0.0039 (9)−0.0004 (9)−0.0004 (9)
C130.0337 (11)0.0319 (12)0.0332 (12)0.0033 (9)0.0031 (10)0.0039 (9)
C140.0400 (12)0.0270 (12)0.0389 (13)0.0067 (9)0.0091 (10)0.0036 (9)
C150.0567 (15)0.0306 (13)0.0404 (14)−0.0062 (11)0.0019 (12)−0.0007 (10)
C160.0550 (15)0.0309 (13)0.0340 (13)−0.0014 (11)0.0022 (11)0.0038 (10)
C170.0378 (12)0.0262 (12)0.0384 (13)0.0066 (9)0.0077 (10)0.0020 (9)
C180.0360 (12)0.0272 (12)0.0388 (13)0.0066 (9)0.0062 (10)−0.0024 (10)
C190.0380 (12)0.0298 (12)0.0363 (13)0.0097 (9)0.0078 (10)−0.0004 (10)
C200.0523 (15)0.0468 (15)0.0387 (14)0.0083 (12)0.0073 (12)0.0026 (11)
C210.0618 (17)0.0634 (19)0.0360 (15)0.0086 (14)0.0007 (13)−0.0053 (13)
C220.0544 (16)0.0535 (17)0.0525 (17)0.0014 (13)−0.0044 (13)−0.0174 (14)
C230.0445 (14)0.0357 (14)0.0539 (16)0.0023 (11)0.0002 (12)−0.0077 (11)
C240.0377 (12)0.0315 (13)0.0448 (15)−0.0028 (10)−0.0008 (11)0.0046 (11)
C250.0448 (14)0.0533 (17)0.0558 (17)−0.0035 (12)0.0062 (13)−0.0083 (13)
C260.0498 (16)0.0559 (19)0.091 (3)−0.0129 (14)0.0027 (16)−0.0235 (18)
C270.0528 (17)0.0409 (17)0.112 (3)−0.0162 (13)0.0163 (18)−0.0035 (18)
C280.0421 (14)0.0373 (14)0.082 (2)−0.0015 (11)0.0219 (14)0.0063 (14)
C290.0315 (11)0.0315 (12)0.0556 (16)0.0040 (9)0.0176 (11)0.0029 (11)
C300.0629 (19)0.0480 (18)0.113 (3)0.0073 (15)0.038 (2)0.0318 (18)
C310.0480 (16)0.072 (2)0.089 (2)0.0135 (15)0.0276 (16)0.0460 (19)
C320.0446 (14)0.0553 (17)0.0543 (17)0.0139 (12)0.0216 (13)0.0246 (13)
C330.0342 (12)0.0353 (13)0.0478 (14)0.0081 (10)0.0179 (11)0.0093 (11)
C340.0582 (17)0.080 (2)0.0435 (16)0.0232 (16)0.0148 (14)0.0234 (15)
C350.0564 (17)0.070 (2)0.0379 (15)0.0158 (15)0.0016 (13)0.0003 (13)
C360.0443 (14)0.0463 (15)0.0389 (14)0.0045 (11)0.0057 (11)−0.0002 (11)

Geometric parameters (Å, °)

Mn1—O12.106 (2)C8—C91.361 (4)
Mn1—O4i2.137 (2)C8—H80.93
Mn1—O52.190 (2)C9—C101.398 (4)
Mn1—O62.545 (2)C9—H90.93
Mn1—O7ii2.182 (2)C10—C111.367 (3)
Mn1—O1W2.157 (2)C10—H100.93
Mn2—O22.125 (2)C11—H110.93
Mn2—O3iii2.173 (2)C13—C141.501 (3)
Mn2—O52.192 (2)C14—C151.364 (3)
Mn2—O8ii2.104 (2)C14—C191.422 (3)
Mn2—N12.273 (2)C15—C161.404 (3)
Mn2—N22.268 (2)C15—H150.93
O1—C11.246 (3)C16—C171.370 (3)
O2—C11.258 (3)C16—H160.93
O3—C121.265 (2)C17—C181.425 (3)
O3—Mn2iv2.1733 (15)C17—C241.500 (3)
O4—C121.244 (3)C18—C231.425 (3)
O4—Mn1v2.1371 (15)C18—C191.428 (3)
O5—C131.274 (3)C19—C201.416 (3)
O6—C131.229 (3)C20—C211.373 (4)
O7—C241.240 (3)C20—H200.93
O7—Mn1vi2.1818 (18)C21—C221.393 (4)
O8—C241.254 (3)C21—H210.93
O8—Mn2vi2.1039 (17)C22—C231.358 (4)
O9—C301.254 (4)C22—H220.93
O10—C311.249 (4)C23—H230.93
O1W—H1W10.852 (10)C25—C261.392 (4)
O1W—H1W20.844 (10)C25—H250.93
N1—C251.330 (3)C26—C271.359 (5)
N1—C291.346 (3)C26—H260.93
N2—C361.335 (3)C27—C281.387 (4)
N2—C331.346 (3)C27—H270.93
C1—C21.507 (3)C28—C291.391 (3)
C2—C31.380 (3)C28—C301.469 (4)
C2—C71.421 (3)C29—C331.470 (3)
C3—C41.403 (3)C30—C311.507 (5)
C3—H30.93C31—C321.471 (4)
C4—C51.367 (3)C32—C341.376 (4)
C4—H40.93C32—C331.403 (3)
C5—C61.436 (3)C34—C351.375 (4)
C5—C121.502 (3)C34—H340.93
C6—C71.422 (3)C35—C361.383 (4)
C6—C111.422 (3)C35—H350.93
C7—C81.423 (3)C36—H360.93
O1—Mn1—O4i178.03 (6)O4—C12—O3124.03 (19)
O1—Mn1—O1W93.82 (7)O4—C12—C5117.92 (18)
O4i—Mn1—O1W88.06 (7)O3—C12—C5118.02 (18)
O1—Mn1—O7ii90.73 (7)O6—C13—O5120.8 (2)
O4i—Mn1—O7ii88.43 (7)O6—C13—C14122.7 (2)
O1W—Mn1—O7ii97.43 (10)O5—C13—C14116.39 (19)
O1—Mn1—O590.97 (6)C15—C14—C19119.9 (2)
O4i—Mn1—O587.72 (6)C15—C14—C13118.1 (2)
O1W—Mn1—O5149.28 (9)C19—C14—C13122.0 (2)
O7ii—Mn1—O5112.85 (6)C14—C15—C16121.6 (2)
O8ii—Mn2—O2101.33 (7)C14—C15—H15119.2
O8ii—Mn2—O3iii95.33 (7)C16—C15—H15119.2
O2—Mn2—O3iii88.39 (6)C17—C16—C15120.3 (2)
O8ii—Mn2—O582.81 (7)C17—C16—H16119.9
O2—Mn2—O590.31 (6)C15—C16—H16119.9
O3iii—Mn2—O5177.48 (6)C16—C17—C18120.0 (2)
O8ii—Mn2—N292.59 (7)C16—C17—C24119.4 (2)
O2—Mn2—N2164.37 (7)C18—C17—C24120.4 (2)
O3iii—Mn2—N297.43 (6)C17—C18—C23122.3 (2)
O5—Mn2—N284.37 (6)C17—C18—C19119.3 (2)
O8ii—Mn2—N1165.15 (8)C23—C18—C19118.5 (2)
O2—Mn2—N193.49 (7)C20—C19—C14122.5 (2)
O3iii—Mn2—N185.94 (7)C20—C19—C18118.7 (2)
O5—Mn2—N196.29 (6)C14—C19—C18118.8 (2)
N2—Mn2—N172.58 (7)C21—C20—C19120.7 (2)
C1—O1—Mn1130.60 (14)C21—C20—H20119.6
C1—O2—Mn2135.86 (15)C19—C20—H20119.6
C12—O3—Mn2iv133.60 (14)C20—C21—C22120.3 (3)
C12—O4—Mn1v134.03 (14)C20—C21—H21119.9
C13—O5—Mn1100.28 (13)C22—C21—H21119.9
C13—O5—Mn2140.78 (14)C23—C22—C21121.2 (3)
Mn1—O5—Mn2105.04 (6)C23—C22—H22119.4
C24—O7—Mn1vi111.36 (16)C21—C22—H22119.4
C24—O8—Mn2vi142.85 (18)C22—C23—C18120.6 (3)
Mn1—O1W—H1W1107 (3)C22—C23—H23119.7
Mn1—O1W—H1W2122 (3)C18—C23—H23119.7
H1W1—O1W—H1W2110.1 (17)O7—C24—O8124.5 (2)
C25—N1—C29118.2 (2)O7—C24—C17119.4 (2)
C25—N1—Mn2124.95 (18)O8—C24—C17116.1 (2)
C29—N1—Mn2116.78 (15)N1—C25—C26123.1 (3)
C36—N2—C33118.2 (2)N1—C25—H25118.5
C36—N2—Mn2124.99 (16)C26—C25—H25118.5
C33—N2—Mn2116.75 (15)C27—C26—C25118.2 (3)
O1—C1—O2126.5 (2)C27—C26—H26120.9
O1—C1—C2115.88 (18)C25—C26—H26120.9
O2—C1—C2117.64 (19)C26—C27—C28120.2 (3)
C3—C2—C7120.04 (19)C26—C27—H27119.9
C3—C2—C1119.28 (19)C28—C27—H27119.9
C7—C2—C1120.53 (19)C27—C28—C29118.1 (3)
C2—C3—C4120.4 (2)C27—C28—C30121.3 (3)
C2—C3—H3119.8C29—C28—C30120.6 (3)
C4—C3—H3119.8N1—C29—C28122.1 (2)
C5—C4—C3121.3 (2)N1—C29—C33116.7 (2)
C5—C4—H4119.3C28—C29—C33121.2 (2)
C3—C4—H4119.3O9—C30—C28122.4 (4)
C4—C5—C6119.96 (19)O9—C30—C31119.5 (3)
C4—C5—C12118.68 (19)C28—C30—C31118.1 (3)
C6—C5—C12121.32 (19)O10—C31—C32121.4 (3)
C7—C6—C11118.5 (2)O10—C31—C30119.5 (3)
C7—C6—C5118.63 (19)C32—C31—C30119.1 (3)
C11—C6—C5122.7 (2)C34—C32—C33118.5 (3)
C6—C7—C2119.54 (19)C34—C32—C31121.8 (3)
C6—C7—C8118.6 (2)C33—C32—C31119.7 (3)
C2—C7—C8121.8 (2)N2—C33—C32121.8 (2)
C9—C8—C7121.2 (2)N2—C33—C29117.1 (2)
C9—C8—H8119.4C32—C33—C29121.1 (2)
C7—C8—H8119.4C35—C34—C32119.9 (2)
C8—C9—C10120.1 (2)C35—C34—H34120.0
C8—C9—H9120.0C32—C34—H34120.0
C10—C9—H9120.0C34—C35—C36118.2 (3)
C11—C10—C9120.9 (2)C34—C35—H35120.9
C11—C10—H10119.6C36—C35—H35120.9
C9—C10—H10119.6N2—C36—C35123.3 (3)
C10—C11—C6120.7 (2)N2—C36—H36118.3
C10—C11—H11119.7C35—C36—H36118.3
C6—C11—H11119.7
O1w—Mn1—O1—C1−164.4 (2)Mn1—O5—C13—O6−0.3 (3)
O7ii—Mn1—O1—C1−66.9 (2)Mn2—O5—C13—O6129.4 (2)
O5—Mn1—O1—C146.0 (2)Mn1—O5—C13—C14176.44 (16)
O8ii—Mn2—O2—C151.2 (3)Mn2—O5—C13—C14−53.8 (3)
O3iii—Mn2—O2—C1146.4 (2)O6—C13—C14—C15111.3 (3)
O5—Mn2—O2—C1−31.5 (2)O5—C13—C14—C15−65.5 (3)
N2—Mn2—O2—C1−101.3 (3)O6—C13—C14—C19−70.4 (3)
N1—Mn2—O2—C1−127.8 (2)O5—C13—C14—C19112.9 (2)
O1—Mn1—O5—C1386.84 (14)C19—C14—C15—C163.0 (4)
O4i—Mn1—O5—C13−94.63 (14)C13—C14—C15—C16−178.6 (2)
O1w—Mn1—O5—C13−12.3 (2)C14—C15—C16—C17−2.5 (4)
O7ii—Mn1—O5—C13178.04 (13)C15—C16—C17—C18−0.7 (3)
O1—Mn1—O5—Mn2−62.92 (7)C15—C16—C17—C24174.5 (2)
O4i—Mn1—O5—Mn2115.60 (7)C16—C17—C18—C23−175.0 (2)
O1w—Mn1—O5—Mn2−162.08 (11)C24—C17—C18—C239.8 (3)
O7ii—Mn1—O5—Mn228.27 (10)C16—C17—C18—C193.3 (3)
O8ii—Mn2—O5—C13−172.7 (2)C24—C17—C18—C19−171.9 (2)
O2—Mn2—O5—C13−71.3 (2)C15—C14—C19—C20177.4 (2)
N2—Mn2—O5—C1394.0 (2)C13—C14—C19—C20−0.9 (3)
N1—Mn2—O5—C1322.2 (2)C15—C14—C19—C18−0.3 (3)
O8ii—Mn2—O5—Mn1−44.29 (8)C13—C14—C19—C18−178.62 (19)
O2—Mn2—O5—Mn157.10 (8)C17—C18—C19—C20179.5 (2)
N2—Mn2—O5—Mn1−137.63 (8)C23—C18—C19—C20−2.2 (3)
N1—Mn2—O5—Mn1150.64 (7)C17—C18—C19—C14−2.8 (3)
O8ii—Mn2—N1—C25176.3 (3)C23—C18—C19—C14175.6 (2)
O2—Mn2—N1—C25−7.4 (2)C14—C19—C20—C21−177.6 (2)
O3iii—Mn2—N1—C2580.76 (19)C18—C19—C20—C210.0 (3)
O5—Mn2—N1—C25−98.1 (2)C19—C20—C21—C222.0 (4)
N2—Mn2—N1—C25179.9 (2)C20—C21—C22—C23−1.9 (4)
O8ii—Mn2—N1—C29−0.9 (4)C21—C22—C23—C18−0.3 (4)
O2—Mn2—N1—C29175.46 (16)C17—C18—C23—C22−179.4 (2)
O3iii—Mn2—N1—C29−96.40 (16)C19—C18—C23—C222.3 (3)
O5—Mn2—N1—C2984.77 (16)Mn1vi—O7—C24—O8−18.2 (3)
N2—Mn2—N1—C292.70 (15)Mn1vi—O7—C24—C17161.82 (17)
O8ii—Mn2—N2—C36−4.72 (19)Mn2vi—O8—C24—O7−45.2 (4)
O2—Mn2—N2—C36148.4 (2)Mn2vi—O8—C24—C17134.8 (2)
O3iii—Mn2—N2—C36−100.44 (18)C16—C17—C24—O764.1 (3)
O5—Mn2—N2—C3677.79 (18)C18—C17—C24—O7−120.7 (3)
N1—Mn2—N2—C36176.2 (2)C16—C17—C24—O8−115.9 (3)
O8ii—Mn2—N2—C33177.08 (15)C18—C17—C24—O859.3 (3)
O2—Mn2—N2—C33−29.8 (3)C29—N1—C25—C26−0.8 (4)
O3iii—Mn2—N2—C3381.36 (15)Mn2—N1—C25—C26−177.9 (2)
O5—Mn2—N2—C33−100.41 (15)N1—C25—C26—C270.9 (4)
N1—Mn2—N2—C33−1.99 (14)C25—C26—C27—C280.1 (5)
Mn1—O1—C1—O2−16.1 (4)C26—C27—C28—C29−1.2 (4)
Mn1—O1—C1—C2163.06 (14)C26—C27—C28—C30178.7 (3)
Mn2—O2—C1—O17.0 (4)C25—N1—C29—C28−0.4 (3)
Mn2—O2—C1—C2−172.07 (16)Mn2—N1—C29—C28177.00 (17)
O1—C1—C2—C356.6 (3)C25—N1—C29—C33179.6 (2)
O2—C1—C2—C3−124.2 (2)Mn2—N1—C29—C33−3.1 (2)
O1—C1—C2—C7−118.8 (2)C27—C28—C29—N11.3 (4)
O2—C1—C2—C760.4 (3)C30—C28—C29—N1−178.5 (2)
C7—C2—C3—C4−1.2 (3)C27—C28—C29—C33−178.6 (2)
C1—C2—C3—C4−176.65 (19)C30—C28—C29—C331.6 (4)
C2—C3—C4—C5−1.8 (3)C27—C28—C30—O9−6.6 (5)
C3—C4—C5—C62.5 (3)C29—C28—C30—O9173.2 (3)
C3—C4—C5—C12−179.48 (19)C27—C28—C30—C31174.9 (3)
C4—C5—C6—C7−0.3 (3)C29—C28—C30—C31−5.2 (4)
C12—C5—C6—C7−178.25 (19)O9—C30—C31—O105.6 (5)
C4—C5—C6—C11175.6 (2)C28—C30—C31—O10−175.9 (3)
C12—C5—C6—C11−2.4 (3)O9—C30—C31—C32−173.1 (3)
C11—C6—C7—C2−178.6 (2)C28—C30—C31—C325.4 (4)
C5—C6—C7—C2−2.6 (3)O10—C31—C32—C34−1.0 (4)
C11—C6—C7—C8−2.4 (3)C30—C31—C32—C34177.7 (3)
C5—C6—C7—C8173.62 (19)O10—C31—C32—C33179.5 (3)
C3—C2—C7—C63.4 (3)C30—C31—C32—C33−1.9 (4)
C1—C2—C7—C6178.75 (19)C36—N2—C33—C321.9 (3)
C3—C2—C7—C8−172.7 (2)Mn2—N2—C33—C32−179.80 (17)
C1—C2—C7—C82.6 (3)C36—N2—C33—C29−177.2 (2)
C6—C7—C8—C90.7 (3)Mn2—N2—C33—C291.2 (2)
C2—C7—C8—C9176.8 (2)C34—C32—C33—N2−0.5 (3)
C7—C8—C9—C101.3 (4)C31—C32—C33—N2179.1 (2)
C8—C9—C10—C11−1.6 (4)C34—C32—C33—C29178.5 (2)
C9—C10—C11—C6−0.1 (4)C31—C32—C33—C29−1.9 (3)
C7—C6—C11—C102.2 (4)N1—C29—C33—N21.3 (3)
C5—C6—C11—C10−173.7 (2)C28—C29—C33—N2−178.8 (2)
Mn1v—O4—C12—O32.2 (4)N1—C29—C33—C32−177.8 (2)
Mn1v—O4—C12—C5−175.79 (15)C28—C29—C33—C322.2 (3)
Mn2iv—O3—C12—O4139.82 (19)C33—C32—C34—C35−1.4 (4)
Mn2iv—O3—C12—C5−42.2 (3)C31—C32—C34—C35179.0 (2)
C4—C5—C12—O4130.1 (2)C32—C34—C35—C361.8 (4)
C6—C5—C12—O4−51.9 (3)C33—N2—C36—C35−1.4 (3)
C4—C5—C12—O3−48.0 (3)Mn2—N2—C36—C35−179.60 (18)
C6—C5—C12—O3130.0 (2)C34—C35—C36—N2−0.4 (4)

Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+3/2, z−1/2; (v) x−1, −y+3/2, z−1/2; (vi) −x+1, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1W1···O3i0.85 (1)1.93 (2)2.720 (2)155 (3)

Symmetry codes: (i) x+1, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2963).

References

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