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Acta Cryst. (2009). E65, m1543    [ doi:10.1107/S1600536809046388 ]

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

F.-D. Cong, F.-Y. Yu, Z. Wei and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] 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.
Poly[aquabis(µ4-naphthalene-1,4-dicarboxylato)(1,10-phenanthroline- 5,6-dione)dimanganese(II)] top
Crystal data top
[Mn2(C12H6O4)2(C12H6N2O2)(H2O)]F(000) = 1552
Mr = 766.42Dx = 1.663 Mg m−3
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 mm−1
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 top
Bruker APEXII area-detector
diffractometer		6015 independent reflections
Radiation source: fine-focus sealed tube4853 reflections with I > 2σ(I)
graphiteRint = 0.025
φ 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 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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 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 Å−3
3 restraintsΔρmin = −0.24 e Å−3
Crystal data top
[Mn2(C12H6O4)2(C12H6N2O2)(H2O)]V = 3061.1 (5) Å3
Mr = 766.42Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.4393 (8) ŵ = 0.90 mm−1
b = 19.2477 (18) ÅT = 293 K
c = 19.2504 (19) Å0.27 × 0.26 × 0.20 mm
β = 101.781 (1)°
Data collection top
Bruker APEXII area-detector
diffractometer		6015 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4853 reflections with I > 2σ(I)
Tmin = 0.794, Tmax = 0.841Rint = 0.025
16986 measured reflectionsθmax = 26.1°
Refinement top
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096Δρmax = 0.40 e Å−3
S = 1.03Δρmin = −0.24 e Å−3
6015 reflectionsAbsolute structure: ?
466 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Selected geometric parameters (Å) top
Mn1—O12.106 (2)Mn2—O22.125 (2)
Mn1—O4i2.137 (2)Mn2—O3iii2.173 (2)
Mn1—O52.190 (2)Mn2—O52.192 (2)
Mn1—O62.545 (2)Mn2—O8ii2.104 (2)
Mn1—O7ii2.182 (2)Mn2—N12.273 (2)
Mn1—O1W2.157 (2)Mn2—N22.268 (2)
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.
Acknowledgements top

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

references
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