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Acta Cryst. (2009). E65, m416    [ doi:10.1107/S1600536809009052 ]

Poly[bis([mu]3-5-nitroisophthalato)bis(1,10-phenanthroline)dimanganese(II)]

H.-D. Wang, M.-M. Li, H.-Y. He and F.-B. Jiang

Abstract top

The title complex, [Mn2(C8H3NO6)2(C12H8N2)2]n, was synthesized under hydrothermal conditions. The structure contains two independent MnII atoms, each coordinated in a distorted octahedral MnN2O4 geometry. [Mn2(phen)2] units (phen = 1,10-phenantroline) are bridged by 5-nitroisophthalate (nip) ligands into ladder-like chains parallel to [100]. Adjacent polymeric chains are linked by C-H...O and [pi]-[pi] interactions [centroid-to-centroid distance = 3.6369 (12) Å] into a two-dimensional framework parallel to (010).

Comment top

Coordination polymers with isophthalate and its derivatives, such as 5-nitroisophthalate (He et al., 2004), 5-sulfoisophthalate (Sun et al., 2003), 5-hydroisophthalate (He et al., 2005) or 5-aminoisophthalate (Wu et al., 2002), have been attracted interest in recent years because of their potential applications and intriguing architectures with new topologies. Here we reported a novel compound, (I), [Mn2(nip)2(phen)2]n (I), where nip = 5-nitroisophthalate and phen = 1,10-phenanthroline.

In the title compound (I), the coordination sphere of the two manganese ions can be best described as distorted octahedral (Fig.1). The carboxyl groups of the nip ligands with µ2-chelating coordination mode to the metal centres show an average Mn—O distance of 2.288 Å, whereas the carboxyl groups with a µ1-bridging mode have an average Mn—O distance of 2.158 Å. The Mn···Mn separation is 7.8156 (5) Å. A one-dimensional ladder-like framework is created by the bridging coordination mode of the nip ligands. Significant π–π stacking interactions exist between adjacent ladders, with a Cg10···Cg10(-x, -y, 1 - z) distance of 3.6369 (12) Å (Cg10 is the centroid of atoms C14–C19) (Fig. 2).

Related literature top

For related isophthalate complexes, see: He et al. (2004, 2005); Sun et al. (2003); Wu et al. (2002).

Experimental top

A mixture of MnSO4.H2O (0.0840 g, 0.5 mmol), 1,10-phenanthroline (0.1980 g, 1 mmol), 5-nitroisophthalic acid (0.2100 g, 1 mmol), 8 ml H2O and 8 ml EtOH was heated at 473 K for 5 d in a 20 ml Teflon-lined stainless-steel autoclave. After cooling, yellow plane-like crystals of the title compound were obtained.

Refinement top

The aromatic H atoms were generated geometrically, and were included in the refinements in the riding model approximation (C—H = 0.93 Å, Uiso = 1.2Ueq(C)).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
[Figure 2] Fig. 2. View of the π–π interactions between the nip ligands.
Poly[bis(µ3-5-nitroisophthalato)bis(1,10-phenanthroline)dimanganese(II)] top
Crystal data top
[Mn2(C8H3NO6)2(C12H8N2)2]V = 1812.69 (4) Å3
Mr = 888.52Z = 2
Triclinic, P1F(000) = 900
Hall symbol: -P 1Dx = 1.628 Mg m−3
a = 10.0602 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.3435 (2) Åθ = 2.3–25.5°
c = 14.6637 (2) ŵ = 0.78 mm−1
α = 104.052 (1)°T = 293 K
β = 102.633 (1)°Plane, yellow
γ = 110.460 (1)°0.28 × 0.23 × 0.19 mm
Data collection top
Bruker SMART CCD
diffractometer		6733 independent reflections
Radiation source: fine-focus sealed tube5771 reflections with I > 2σ(I)
graphiteRint = 0.021
φ and ω scansθmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		h = −11→12
Tmin = 0.82, Tmax = 0.90k = −17→16
19255 measured reflectionsl = −17→17
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0319P)2 + 1.1304P]
where P = (Fo2 + 2Fc2)/3
6733 reflections(Δ/σ)max < 0.001
541 parametersΔρmax = 0.38 e Å−3
0 restraintsΔρmin = −0.28 e Å−3
Crystal data top
[Mn2(C8H3NO6)2(C12H8N2)2]γ = 110.460 (1)°
Mr = 888.52V = 1812.69 (4) Å3
Triclinic, P1Z = 2
a = 10.0602 (1) ÅMo Kα radiation
b = 14.3435 (2) ŵ = 0.78 mm−1
c = 14.6637 (2) ÅT = 293 K
α = 104.052 (1)°0.28 × 0.23 × 0.19 mm
β = 102.633 (1)°
Data collection top
Bruker SMART CCD
diffractometer		6733 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)		5771 reflections with I > 2σ(I)
Tmin = 0.82, Tmax = 0.90Rint = 0.021
19255 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.082Δρmax = 0.38 e Å−3
S = 1.05Δρmin = −0.28 e Å−3
6733 reflectionsAbsolute structure: ?
541 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
O6−0.38999 (16)0.07873 (13)0.39068 (12)0.0419 (4)
O120.48532 (16)0.06651 (13)0.14855 (12)0.0448 (4)
O100.0320 (2)−0.28100 (15)0.00966 (16)0.0681 (6)
O9−0.1856 (2)−0.28002 (15)−0.02566 (18)0.0761 (7)
C40−0.2137 (2)0.40567 (17)0.18610 (17)0.0376 (5)
C39−0.3176 (2)0.33731 (19)0.08772 (17)0.0389 (5)
C38−0.4691 (3)0.1676 (2)−0.02115 (18)0.0501 (6)
H38−0.50580.0946−0.03580.060*
C37−0.5213 (3)0.2053 (3)−0.0939 (2)0.0665 (9)
H37−0.59290.1580−0.15520.080*
C36−0.4671 (3)0.3113 (3)−0.0749 (2)0.0695 (9)
H36−0.49990.3370−0.12360.083*
Mn10.50277 (3)0.18469 (2)0.40921 (2)0.02943 (9)
Mn2−0.28274 (3)0.18118 (3)0.19550 (2)0.03242 (9)
O5−0.22209 (16)0.19531 (12)0.35061 (11)0.0364 (3)
O110.46448 (15)0.19055 (12)0.26097 (11)0.0372 (4)
O10.28394 (16)0.18994 (12)0.41974 (13)0.0444 (4)
O8−0.04288 (18)0.19540 (13)0.18704 (14)0.0502 (4)
N5−0.18114 (19)0.35909 (14)0.25249 (13)0.0350 (4)
C140.0582 (2)0.03847 (16)0.38410 (14)0.0278 (4)
N10.60980 (19)0.36391 (14)0.47322 (15)0.0375 (4)
C17−0.2442 (2)−0.05564 (16)0.36682 (15)0.0314 (5)
H17−0.3447−0.08760.36190.038*
O20.29375 (16)0.03586 (12)0.38289 (13)0.0439 (4)
C22−0.0057 (2)0.03872 (16)0.13375 (14)0.0286 (4)
C240.2403 (2)0.04240 (16)0.14906 (14)0.0286 (4)
N20.61892 (19)0.23126 (13)0.57383 (13)0.0336 (4)
C19−0.0278 (2)0.09562 (16)0.38222 (15)0.0281 (4)
H190.01600.16610.38670.034*
C21−0.1018 (2)0.09678 (18)0.15297 (15)0.0330 (5)
C15−0.0072 (2)−0.06723 (16)0.37599 (15)0.0313 (4)
H150.0485−0.10710.37630.038*
C18−0.1786 (2)0.04910 (16)0.37374 (14)0.0283 (4)
C27−0.0717 (2)−0.06970 (17)0.08307 (15)0.0321 (5)
H27−0.1756−0.10820.06120.038*
C260.0202 (2)−0.11973 (16)0.06560 (15)0.0315 (4)
C250.1751 (2)−0.06559 (17)0.09654 (15)0.0315 (5)
H250.2340−0.10100.08240.038*
O7−0.23937 (16)0.04323 (13)0.13500 (13)0.0472 (4)
C16−0.1575 (2)−0.11164 (16)0.36741 (15)0.0311 (4)
C130.2228 (2)0.09112 (17)0.39602 (15)0.0311 (5)
C230.1499 (2)0.09427 (16)0.16730 (14)0.0291 (4)
H230.19420.16700.20240.035*
C32−0.1522 (3)0.51645 (19)0.2104 (2)0.0501 (6)
C110.6698 (2)0.33550 (17)0.62839 (17)0.0367 (5)
C280.4087 (2)0.10391 (17)0.18864 (16)0.0330 (5)
C20−0.2706 (2)0.11226 (17)0.37167 (15)0.0313 (5)
N4−0.0494 (2)−0.23528 (16)0.01253 (15)0.0468 (5)
N3−0.2287 (2)−0.22294 (15)0.35983 (16)0.0441 (5)
C120.6636 (2)0.40590 (17)0.57451 (18)0.0378 (5)
N6−0.3696 (2)0.23105 (15)0.06785 (14)0.0385 (4)
C100.6353 (3)0.1663 (2)0.62129 (19)0.0439 (6)
H100.60120.09500.58400.053*
O4−0.3650 (2)−0.27042 (15)0.32496 (17)0.0670 (6)
O3−0.1460 (2)−0.26194 (15)0.39173 (19)0.0714 (6)
C10.6126 (3)0.4296 (2)0.4231 (2)0.0499 (6)
H10.57660.40190.35380.060*
C40.7204 (3)0.51567 (18)0.6283 (2)0.0519 (7)
C20.6685 (3)0.5404 (2)0.4716 (3)0.0638 (9)
H20.66930.58460.43450.077*
C30−0.0212 (3)0.5308 (2)0.3741 (2)0.0546 (7)
H300.04330.57140.43920.066*
C29−0.0876 (3)0.4210 (2)0.34357 (18)0.0446 (6)
H29−0.06520.38930.38940.054*
C35−0.3611 (3)0.3823 (2)0.0185 (2)0.0549 (7)
C70.7351 (3)0.3753 (2)0.73312 (19)0.0490 (6)
C80.7495 (3)0.3033 (3)0.7796 (2)0.0589 (7)
H80.79250.32660.84860.071*
C30.7210 (3)0.5818 (2)0.5727 (3)0.0640 (9)
H30.75760.65460.60500.077*
C31−0.0517 (3)0.5781 (2)0.3078 (2)0.0567 (8)
H31−0.00580.65170.32680.068*
C90.7013 (3)0.1998 (2)0.7248 (2)0.0579 (7)
H90.71190.15190.75530.070*
C50.7804 (3)0.5524 (2)0.7353 (2)0.0667 (9)
H50.81520.62420.77120.080*
C34−0.2953 (4)0.4958 (3)0.0461 (3)0.0738 (9)
H34−0.32310.52600.00010.089*
C60.7876 (3)0.4866 (2)0.7845 (2)0.0639 (8)
H60.82770.51360.85380.077*
C33−0.1950 (4)0.5589 (2)0.1364 (3)0.0714 (9)
H33−0.15220.63200.15130.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O60.0319 (8)0.0502 (10)0.0609 (10)0.0265 (7)0.0254 (7)0.0257 (8)
O120.0266 (8)0.0531 (10)0.0569 (10)0.0196 (7)0.0187 (7)0.0144 (8)
O100.0729 (13)0.0406 (10)0.0867 (15)0.0330 (10)0.0180 (11)0.0098 (10)
O90.0470 (12)0.0384 (11)0.1048 (17)0.0026 (9)0.0096 (11)−0.0006 (11)
C400.0331 (11)0.0355 (12)0.0498 (13)0.0176 (10)0.0188 (10)0.0152 (10)
C390.0351 (12)0.0439 (13)0.0448 (13)0.0198 (10)0.0175 (10)0.0190 (10)
C380.0410 (13)0.0538 (15)0.0413 (13)0.0129 (12)0.0096 (11)0.0077 (11)
C370.0500 (16)0.093 (2)0.0393 (15)0.0191 (16)0.0061 (12)0.0194 (15)
C360.0623 (19)0.101 (3)0.0581 (18)0.0363 (19)0.0194 (15)0.0475 (18)
Mn10.02107 (15)0.02731 (17)0.04103 (19)0.01103 (13)0.01000 (13)0.01304 (13)
Mn20.02599 (17)0.03180 (18)0.04039 (19)0.01458 (14)0.01036 (13)0.01137 (14)
O50.0333 (8)0.0370 (8)0.0446 (9)0.0201 (7)0.0102 (7)0.0181 (7)
O110.0267 (7)0.0370 (8)0.0413 (8)0.0108 (7)0.0039 (6)0.0134 (7)
O10.0266 (8)0.0334 (9)0.0736 (12)0.0121 (7)0.0180 (8)0.0190 (8)
O80.0402 (9)0.0402 (10)0.0769 (12)0.0239 (8)0.0249 (9)0.0170 (9)
N50.0273 (9)0.0353 (10)0.0409 (10)0.0133 (8)0.0123 (8)0.0099 (8)
C140.0232 (10)0.0341 (11)0.0315 (10)0.0142 (9)0.0111 (8)0.0154 (9)
N10.0282 (9)0.0327 (10)0.0608 (12)0.0155 (8)0.0189 (9)0.0242 (9)
C170.0226 (10)0.0362 (12)0.0368 (11)0.0125 (9)0.0116 (8)0.0136 (9)
O20.0280 (8)0.0415 (9)0.0746 (12)0.0215 (7)0.0233 (8)0.0252 (8)
C220.0246 (10)0.0351 (11)0.0287 (10)0.0149 (9)0.0091 (8)0.0119 (9)
C240.0244 (10)0.0361 (11)0.0291 (10)0.0150 (9)0.0096 (8)0.0139 (9)
N20.0292 (9)0.0283 (9)0.0435 (10)0.0126 (8)0.0107 (8)0.0133 (8)
C190.0243 (10)0.0307 (11)0.0334 (10)0.0135 (8)0.0100 (8)0.0149 (9)
C210.0272 (11)0.0426 (13)0.0310 (11)0.0191 (10)0.0082 (8)0.0109 (9)
C150.0304 (10)0.0336 (11)0.0391 (11)0.0194 (9)0.0154 (9)0.0159 (9)
C180.0248 (10)0.0363 (11)0.0291 (10)0.0170 (9)0.0101 (8)0.0134 (9)
C270.0224 (10)0.0378 (12)0.0329 (11)0.0099 (9)0.0080 (8)0.0127 (9)
C260.0327 (11)0.0284 (11)0.0318 (11)0.0120 (9)0.0102 (9)0.0099 (9)
C250.0321 (11)0.0399 (12)0.0325 (11)0.0225 (10)0.0142 (9)0.0154 (9)
O70.0229 (8)0.0509 (10)0.0599 (10)0.0172 (7)0.0119 (7)0.0056 (8)
C160.0311 (11)0.0279 (11)0.0371 (11)0.0129 (9)0.0145 (9)0.0129 (9)
C130.0235 (10)0.0391 (12)0.0369 (11)0.0154 (9)0.0110 (8)0.0194 (9)
C230.0253 (10)0.0319 (11)0.0297 (10)0.0126 (9)0.0094 (8)0.0094 (8)
C320.0480 (14)0.0356 (13)0.0738 (18)0.0196 (11)0.0302 (13)0.0194 (13)
C110.0246 (10)0.0307 (11)0.0489 (13)0.0094 (9)0.0115 (9)0.0082 (10)
C280.0242 (10)0.0412 (12)0.0401 (12)0.0163 (9)0.0111 (9)0.0208 (10)
C200.0260 (10)0.0379 (12)0.0333 (11)0.0188 (9)0.0081 (8)0.0117 (9)
N40.0497 (13)0.0338 (11)0.0506 (12)0.0151 (10)0.0138 (10)0.0109 (9)
N30.0424 (12)0.0325 (10)0.0636 (13)0.0160 (9)0.0270 (10)0.0187 (9)
C120.0248 (10)0.0259 (11)0.0588 (15)0.0092 (9)0.0148 (10)0.0097 (10)
N60.0327 (10)0.0395 (11)0.0397 (10)0.0141 (8)0.0106 (8)0.0111 (8)
C100.0426 (13)0.0416 (13)0.0533 (14)0.0207 (11)0.0156 (11)0.0225 (11)
O40.0408 (11)0.0435 (11)0.1003 (16)0.0024 (9)0.0177 (10)0.0266 (10)
O30.0638 (12)0.0459 (11)0.135 (2)0.0354 (10)0.0515 (13)0.0480 (12)
C10.0404 (13)0.0486 (15)0.0824 (19)0.0252 (12)0.0301 (13)0.0409 (14)
C40.0338 (12)0.0274 (12)0.089 (2)0.0111 (10)0.0233 (13)0.0107 (13)
C20.0478 (15)0.0481 (16)0.128 (3)0.0280 (13)0.0463 (18)0.0592 (19)
C300.0397 (14)0.0488 (15)0.0542 (16)0.0086 (12)0.0180 (12)−0.0037 (13)
C290.0340 (12)0.0486 (14)0.0428 (13)0.0132 (11)0.0131 (10)0.0083 (11)
C350.0543 (16)0.0678 (18)0.0600 (17)0.0316 (14)0.0250 (13)0.0371 (14)
C70.0329 (12)0.0509 (15)0.0488 (14)0.0114 (11)0.0128 (11)0.0039 (12)
C80.0495 (15)0.080 (2)0.0447 (15)0.0256 (15)0.0141 (12)0.0220 (15)
C30.0438 (15)0.0281 (13)0.125 (3)0.0159 (12)0.0350 (17)0.0273 (16)
C310.0475 (15)0.0306 (13)0.081 (2)0.0108 (11)0.0329 (14)0.0002 (13)
C90.0571 (16)0.0697 (19)0.0569 (16)0.0292 (15)0.0191 (13)0.0351 (15)
C50.0463 (16)0.0359 (15)0.088 (2)0.0083 (12)0.0192 (15)−0.0120 (15)
C340.084 (2)0.072 (2)0.093 (2)0.0406 (19)0.035 (2)0.058 (2)
C60.0556 (17)0.0533 (17)0.0577 (17)0.0140 (14)0.0161 (14)−0.0060 (14)
C330.081 (2)0.0463 (17)0.105 (3)0.0306 (16)0.044 (2)0.0396 (18)
Geometric parameters (Å, °) top
O6—C201.249 (3)C24—C231.391 (3)
O6—Mn1i2.1498 (15)C24—C281.504 (3)
O12—C281.250 (3)N2—C101.323 (3)
O12—Mn2ii2.1652 (15)N2—C111.357 (3)
O10—N41.216 (3)C19—C181.390 (3)
O9—N41.216 (3)C19—H190.9300
C40—N51.353 (3)C21—O71.254 (3)
C40—C321.406 (3)C15—C161.383 (3)
C40—C391.440 (3)C15—H150.9300
C39—N61.357 (3)C18—C201.505 (3)
C39—C351.400 (3)C27—C261.383 (3)
C38—N61.322 (3)C27—H270.9300
C38—C371.393 (4)C26—C251.382 (3)
C38—H380.9300C26—N41.472 (3)
C37—C361.355 (4)C25—H250.9300
C37—H370.9300C16—N31.467 (3)
C36—C351.405 (4)C23—H230.9300
C36—H360.9300C32—C311.405 (4)
Mn1—O6ii2.1498 (15)C32—C331.426 (4)
Mn1—O112.1508 (15)C11—C71.409 (3)
Mn1—N22.2531 (18)C11—C121.434 (3)
Mn1—N12.2584 (18)N3—O41.216 (3)
Mn1—O12.2661 (15)N3—O31.227 (3)
Mn1—O22.2879 (15)C12—C41.414 (3)
Mn1—C132.600 (2)C10—C91.399 (4)
Mn2—O52.1608 (15)C10—H100.9300
Mn2—O12i2.1652 (15)C1—C21.415 (4)
Mn2—O72.1938 (16)C1—H10.9300
Mn2—N52.2411 (18)C4—C31.392 (4)
Mn2—N62.2697 (19)C4—C51.437 (4)
Mn2—O82.3830 (16)C2—C31.356 (4)
Mn2—C212.615 (2)C2—H20.9300
O5—C201.261 (3)C30—C311.356 (4)
O11—C281.263 (3)C30—C291.384 (4)
O1—C131.251 (3)C30—H300.9300
O8—C211.242 (3)C29—H290.9300
N5—C291.322 (3)C35—C341.435 (4)
C14—C191.385 (3)C7—C81.399 (4)
C14—C151.388 (3)C7—C61.431 (4)
C14—C131.509 (3)C8—C91.353 (4)
N1—C11.324 (3)C8—H80.9300
N1—C121.359 (3)C3—H30.9300
C17—C161.377 (3)C31—H310.9300
C17—C181.381 (3)C9—H90.9300
C17—H170.9300C5—C61.331 (4)
O2—C131.247 (2)C5—H50.9300
C22—C271.383 (3)C34—C331.337 (5)
C22—C231.389 (3)C34—H340.9300
C22—C211.508 (3)C6—H60.9300
C24—C251.383 (3)C33—H330.9300
C20—O6—Mn1i115.68 (14)C17—C18—C19119.77 (18)
C28—O12—Mn2ii112.02 (14)C17—C18—C20119.94 (18)
N5—C40—C32122.6 (2)C19—C18—C20120.29 (18)
N5—C40—C39117.5 (2)C22—C27—C26118.63 (18)
C32—C40—C39119.9 (2)C22—C27—H27120.7
N6—C39—C35123.5 (2)C26—C27—H27120.7
N6—C39—C40117.1 (2)C25—C26—C27122.58 (19)
C35—C39—C40119.4 (2)C25—C26—N4118.62 (19)
N6—C38—C37122.9 (3)C27—C26—N4118.80 (19)
N6—C38—H38118.6C26—C25—C24118.43 (19)
C37—C38—H38118.6C26—C25—H25120.8
C36—C37—C38119.6 (3)C24—C25—H25120.8
C36—C37—H37120.2C21—O7—Mn294.70 (13)
C38—C37—H37120.2C17—C16—C15122.94 (19)
C37—C36—C35119.9 (3)C17—C16—N3117.91 (18)
C37—C36—H36120.0C15—C16—N3119.14 (19)
C35—C36—H36120.0O2—C13—O1122.15 (18)
O6ii—Mn1—O1196.15 (6)O2—C13—C14119.64 (19)
O6ii—Mn1—N285.35 (6)O1—C13—C14118.21 (18)
O11—Mn1—N2158.99 (6)O2—C13—Mn161.62 (11)
O6ii—Mn1—N1128.76 (6)O1—C13—Mn160.62 (10)
O11—Mn1—N189.95 (6)C14—C13—Mn1177.21 (14)
N2—Mn1—N173.18 (7)C22—C23—C24120.76 (19)
O6ii—Mn1—O1141.93 (6)C22—C23—H23119.6
O11—Mn1—O194.75 (6)C24—C23—H23119.6
N2—Mn1—O196.89 (6)C31—C32—C40116.7 (3)
N1—Mn1—O187.53 (6)C31—C32—C33124.4 (3)
O6ii—Mn1—O284.74 (6)C40—C32—C33118.9 (3)
O11—Mn1—O2100.62 (6)N2—C11—C7122.2 (2)
N2—Mn1—O2100.39 (6)N2—C11—C12117.1 (2)
N1—Mn1—O2143.83 (6)C7—C11—C12120.6 (2)
O1—Mn1—O257.39 (5)O12—C28—O11123.81 (19)
O6ii—Mn1—C13113.37 (6)O12—C28—C24118.37 (19)
O11—Mn1—C1397.86 (6)O11—C28—C24117.83 (18)
N2—Mn1—C13100.76 (6)O6—C20—O5124.43 (19)
N1—Mn1—C13116.04 (7)O6—C20—C18117.77 (19)
O1—Mn1—C1328.76 (6)O5—C20—C18117.80 (18)
O2—Mn1—C1328.66 (6)O9—N4—O10123.5 (2)
O5—Mn2—O12i97.51 (6)O9—N4—C26118.1 (2)
O5—Mn2—O798.78 (6)O10—N4—C26118.4 (2)
O12i—Mn2—O785.02 (6)O4—N3—O3123.7 (2)
O5—Mn2—N585.80 (6)O4—N3—C16118.8 (2)
O12i—Mn2—N5130.44 (6)O3—N3—C16117.42 (19)
O7—Mn2—N5143.60 (6)N1—C12—C4123.1 (2)
O5—Mn2—N6152.61 (6)N1—C12—C11117.88 (19)
O12i—Mn2—N683.95 (7)C4—C12—C11119.0 (2)
O7—Mn2—N6108.58 (7)C38—N6—C39117.6 (2)
N5—Mn2—N673.03 (7)C38—N6—Mn2126.66 (17)
O5—Mn2—O893.04 (6)C39—N6—Mn2115.68 (14)
O12i—Mn2—O8141.58 (6)N2—C10—C9123.2 (2)
O7—Mn2—O856.82 (6)N2—C10—H10118.4
N5—Mn2—O886.99 (6)C9—C10—H10118.4
N6—Mn2—O8102.76 (7)N1—C1—C2122.2 (3)
O5—Mn2—C2195.56 (6)N1—C1—H1118.9
O12i—Mn2—C21113.56 (7)C2—C1—H1118.9
O7—Mn2—C2128.56 (6)C3—C4—C12116.9 (3)
N5—Mn2—C21115.28 (7)C3—C4—C5124.3 (3)
N6—Mn2—C21108.99 (7)C12—C4—C5118.6 (3)
O8—Mn2—C2128.30 (6)C3—C2—C1119.5 (3)
C20—O5—Mn2118.39 (13)C3—C2—H2120.3
C28—O11—Mn1118.01 (13)C1—C2—H2120.3
C13—O1—Mn190.62 (12)C31—C30—C29119.0 (2)
C21—O8—Mn286.27 (12)C31—C30—H30120.5
C29—N5—C40118.1 (2)C29—C30—H30120.5
C29—N5—Mn2125.24 (17)N5—C29—C30123.3 (3)
C40—N5—Mn2116.54 (14)N5—C29—H29118.3
C19—C14—C15119.72 (18)C30—C29—H29118.3
C19—C14—C13120.20 (18)C39—C35—C36116.5 (3)
C15—C14—C13120.08 (18)C39—C35—C34119.0 (3)
C1—N1—C12118.1 (2)C36—C35—C34124.5 (3)
C1—N1—Mn1126.84 (18)C8—C7—C11117.3 (2)
C12—N1—Mn1114.78 (14)C8—C7—C6124.3 (3)
C16—C17—C18118.46 (18)C11—C7—C6118.4 (3)
C16—C17—H17120.8C9—C8—C7120.4 (3)
C18—C17—H17120.8C9—C8—H8119.8
C13—O2—Mn189.73 (12)C7—C8—H8119.8
C27—C22—C23119.70 (19)C2—C3—C4120.2 (3)
C27—C22—C21120.40 (18)C2—C3—H3119.9
C23—C22—C21119.90 (18)C4—C3—H3119.9
C25—C24—C23119.88 (18)C30—C31—C32120.2 (2)
C25—C24—C28120.45 (18)C30—C31—H31119.9
C23—C24—C28119.65 (18)C32—C31—H31119.9
C10—N2—C11118.2 (2)C8—C9—C10118.7 (3)
C10—N2—Mn1126.20 (15)C8—C9—H9120.6
C11—N2—Mn1115.51 (14)C10—C9—H9120.6
C14—C19—C18120.95 (19)C6—C5—C4121.9 (2)
C14—C19—H19119.5C6—C5—H5119.0
C18—C19—H19119.5C4—C5—H5119.0
O8—C21—O7122.0 (2)C33—C34—C35121.4 (3)
O8—C21—C22119.48 (18)C33—C34—H34119.3
O7—C21—C22118.48 (19)C35—C34—H34119.3
O8—C21—Mn265.43 (11)C5—C6—C7121.4 (3)
O7—C21—Mn256.74 (11)C5—C6—H6119.3
C22—C21—Mn2173.29 (16)C7—C6—H6119.3
C16—C15—C14118.16 (19)C34—C33—C32121.4 (3)
C16—C15—H15120.9C34—C33—H33119.3
C14—C15—H15120.9C32—C33—H33119.3
N5—C40—C39—N6−2.9 (3)Mn1—O1—C13—C14−177.10 (16)
C32—C40—C39—N6178.1 (2)C19—C14—C13—O2−169.39 (19)
N5—C40—C39—C35176.4 (2)C15—C14—C13—O211.3 (3)
C32—C40—C39—C35−2.6 (3)C19—C14—C13—O111.1 (3)
N6—C38—C37—C361.3 (4)C15—C14—C13—O1−168.2 (2)
C38—C37—C36—C35−1.2 (5)C19—C14—C13—Mn1−53 (3)
O12i—Mn2—O5—C2040.49 (15)C15—C14—C13—Mn1127 (3)
O7—Mn2—O5—C20−45.60 (15)O6ii—Mn1—C13—O2−2.45 (15)
N5—Mn2—O5—C20170.76 (15)O11—Mn1—C13—O297.78 (13)
N6—Mn2—O5—C20131.83 (16)N2—Mn1—C13—O2−92.00 (13)
O8—Mn2—O5—C20−102.49 (14)N1—Mn1—C13—O2−168.40 (13)
C21—Mn2—O5—C20−74.21 (15)O1—Mn1—C13—O2−176.7 (2)
O6ii—Mn1—O11—C2847.12 (15)O6ii—Mn1—C13—O1174.24 (12)
N2—Mn1—O11—C28140.16 (18)O11—Mn1—C13—O1−85.53 (13)
N1—Mn1—O11—C28176.14 (15)N2—Mn1—C13—O184.69 (13)
O1—Mn1—O11—C28−96.34 (15)N1—Mn1—C13—O18.28 (15)
O2—Mn1—O11—C28−38.66 (15)O2—Mn1—C13—O1176.7 (2)
C13—Mn1—O11—C28−67.57 (15)O6ii—Mn1—C13—C14−120 (3)
O6ii—Mn1—O1—C13−8.59 (18)O11—Mn1—C13—C14−20 (3)
O11—Mn1—O1—C1397.70 (13)N2—Mn1—C13—C14151 (3)
N2—Mn1—O1—C13−99.83 (13)N1—Mn1—C13—C1474 (3)
N1—Mn1—O1—C13−172.56 (14)O1—Mn1—C13—C1466 (3)
O2—Mn1—O1—C13−1.89 (12)O2—Mn1—C13—C14−117 (3)
O5—Mn2—O8—C2196.07 (13)C27—C22—C23—C241.1 (3)
O12i—Mn2—O8—C21−10.06 (19)C21—C22—C23—C24−179.07 (18)
O7—Mn2—O8—C21−2.43 (13)C25—C24—C23—C220.3 (3)
N5—Mn2—O8—C21−178.30 (14)C28—C24—C23—C22−178.33 (18)
N6—Mn2—O8—C21−106.46 (14)N5—C40—C32—C311.0 (3)
C32—C40—N5—C29−0.1 (3)C39—C40—C32—C31180.0 (2)
C39—C40—N5—C29−179.0 (2)N5—C40—C32—C33−178.8 (2)
C32—C40—N5—Mn2−177.03 (17)C39—C40—C32—C330.2 (4)
C39—C40—N5—Mn24.0 (2)C10—N2—C11—C7−1.7 (3)
O5—Mn2—N5—C2918.08 (18)Mn1—N2—C11—C7175.40 (17)
O12i—Mn2—N5—C29114.38 (18)C10—N2—C11—C12174.33 (19)
O7—Mn2—N5—C29−81.0 (2)Mn1—N2—C11—C12−8.6 (2)
N6—Mn2—N5—C29−179.51 (19)Mn2ii—O12—C28—O11−12.1 (3)
O8—Mn2—N5—C29−75.20 (18)Mn2ii—O12—C28—C24168.14 (14)
C21—Mn2—N5—C29−76.09 (19)Mn1—O11—C28—O12−95.4 (2)
O5—Mn2—N5—C40−165.19 (15)Mn1—O11—C28—C2484.41 (19)
O12i—Mn2—N5—C40−68.89 (17)C25—C24—C28—O1222.4 (3)
O7—Mn2—N5—C4095.70 (17)C23—C24—C28—O12−159.0 (2)
N6—Mn2—N5—C40−2.78 (15)C25—C24—C28—O11−157.41 (19)
O8—Mn2—N5—C40101.53 (15)C23—C24—C28—O1121.2 (3)
C21—Mn2—N5—C40100.64 (15)Mn1i—O6—C20—O5−9.5 (3)
O6ii—Mn1—N1—C1106.59 (18)Mn1i—O6—C20—C18170.71 (13)
O11—Mn1—N1—C18.73 (18)Mn2—O5—C20—O6−92.3 (2)
N2—Mn1—N1—C1176.01 (19)Mn2—O5—C20—C1887.53 (18)
O1—Mn1—N1—C1−86.03 (18)C17—C18—C20—O619.0 (3)
O2—Mn1—N1—C1−99.4 (2)C19—C18—C20—O6−161.27 (19)
C13—Mn1—N1—C1−90.01 (19)C17—C18—C20—O5−160.86 (19)
O6ii—Mn1—N1—C12−79.94 (16)C19—C18—C20—O518.9 (3)
O11—Mn1—N1—C12−177.81 (14)C25—C26—N4—O9−170.6 (2)
N2—Mn1—N1—C12−10.52 (14)C27—C26—N4—O99.8 (3)
O1—Mn1—N1—C1287.43 (15)C25—C26—N4—O109.8 (3)
O2—Mn1—N1—C1274.05 (18)C27—C26—N4—O10−169.8 (2)
C13—Mn1—N1—C1283.46 (15)C17—C16—N3—O421.2 (3)
O6ii—Mn1—O2—C13177.74 (14)C15—C16—N3—O4−159.6 (2)
O11—Mn1—O2—C13−86.96 (13)C17—C16—N3—O3−157.0 (2)
N2—Mn1—O2—C1393.47 (13)C15—C16—N3—O322.2 (3)
N1—Mn1—O2—C1317.82 (19)C1—N1—C12—C40.7 (3)
O1—Mn1—O2—C131.89 (12)Mn1—N1—C12—C4−173.37 (17)
O6ii—Mn1—N2—C10−40.21 (18)C1—N1—C12—C11−175.89 (19)
O11—Mn1—N2—C10−135.3 (2)Mn1—N1—C12—C1110.0 (2)
N1—Mn1—N2—C10−173.1 (2)N2—C11—C12—N1−1.0 (3)
O1—Mn1—N2—C10101.58 (18)C7—C11—C12—N1175.04 (19)
O2—Mn1—N2—C1043.56 (19)N2—C11—C12—C4−177.75 (19)
C13—Mn1—N2—C1072.73 (19)C7—C11—C12—C4−1.7 (3)
O6ii—Mn1—N2—C11143.00 (15)C37—C38—N6—C390.1 (4)
O11—Mn1—N2—C1148.0 (3)C37—C38—N6—Mn2177.1 (2)
N1—Mn1—N2—C1110.10 (14)C35—C39—N6—C38−1.5 (3)
O1—Mn1—N2—C11−75.21 (15)C40—C39—N6—C38177.7 (2)
O2—Mn1—N2—C11−133.23 (14)C35—C39—N6—Mn2−178.89 (19)
C13—Mn1—N2—C11−104.06 (15)C40—C39—N6—Mn20.4 (2)
C15—C14—C19—C180.9 (3)O5—Mn2—N6—C38−134.94 (19)
C13—C14—C19—C18−178.42 (18)O12i—Mn2—N6—C38−40.3 (2)
Mn2—O8—C21—O74.2 (2)O7—Mn2—N6—C3842.4 (2)
Mn2—O8—C21—C22−174.86 (17)N5—Mn2—N6—C38−175.9 (2)
C27—C22—C21—O8−170.9 (2)O8—Mn2—N6—C38101.3 (2)
C23—C22—C21—O89.3 (3)C21—Mn2—N6—C3872.6 (2)
C27—C22—C21—O710.0 (3)O5—Mn2—N6—C3942.1 (2)
C23—C22—C21—O7−169.81 (19)O12i—Mn2—N6—C39136.80 (16)
C27—C22—C21—Mn253.3 (13)O7—Mn2—N6—C39−140.54 (15)
C23—C22—C21—Mn2−126.5 (12)N5—Mn2—N6—C391.21 (15)
O5—Mn2—C21—O8−86.09 (14)O8—Mn2—N6—C39−81.60 (16)
O12i—Mn2—C21—O8173.20 (13)C21—Mn2—N6—C39−110.34 (16)
O7—Mn2—C21—O8175.7 (2)C11—N2—C10—C90.5 (3)
N5—Mn2—C21—O81.88 (15)Mn1—N2—C10—C9−176.24 (18)
N6—Mn2—C21—O881.57 (14)C12—N1—C1—C2−0.3 (3)
O5—Mn2—C21—O798.17 (14)Mn1—N1—C1—C2172.97 (17)
O12i—Mn2—C21—O7−2.53 (15)N1—C12—C4—C3−0.6 (3)
N5—Mn2—C21—O7−173.86 (13)C11—C12—C4—C3175.9 (2)
N6—Mn2—C21—O7−94.16 (14)N1—C12—C4—C5−177.4 (2)
O8—Mn2—C21—O7−175.7 (2)C11—C12—C4—C5−0.8 (3)
O5—Mn2—C21—C2252.1 (12)N1—C1—C2—C3−0.2 (4)
O12i—Mn2—C21—C22−48.6 (12)C40—N5—C29—C30−0.2 (3)
O7—Mn2—C21—C22−46.1 (12)Mn2—N5—C29—C30176.50 (18)
N5—Mn2—C21—C22140.0 (12)C31—C30—C29—N5−0.6 (4)
N6—Mn2—C21—C22−140.3 (12)N6—C39—C35—C361.6 (4)
O8—Mn2—C21—C22138.2 (13)C40—C39—C35—C36−177.7 (2)
C19—C14—C15—C16−0.8 (3)N6—C39—C35—C34−177.9 (2)
C13—C14—C15—C16178.59 (19)C40—C39—C35—C342.8 (4)
C16—C17—C18—C19−0.7 (3)C37—C36—C35—C39−0.1 (4)
C16—C17—C18—C20179.02 (18)C37—C36—C35—C34179.3 (3)
C14—C19—C18—C17−0.2 (3)N2—C11—C7—C81.6 (3)
C14—C19—C18—C20−179.92 (18)C12—C11—C7—C8−174.3 (2)
C23—C22—C27—C26−1.1 (3)N2—C11—C7—C6179.1 (2)
C21—C22—C27—C26179.01 (19)C12—C11—C7—C63.2 (3)
C22—C27—C26—C25−0.2 (3)C11—C7—C8—C9−0.3 (4)
C22—C27—C26—N4179.41 (19)C6—C7—C8—C9−177.6 (3)
C27—C26—C25—C241.6 (3)C1—C2—C3—C40.2 (4)
N4—C26—C25—C24−178.03 (19)C12—C4—C3—C20.1 (4)
C23—C24—C25—C26−1.6 (3)C5—C4—C3—C2176.7 (3)
C28—C24—C25—C26177.04 (19)C29—C30—C31—C321.7 (4)
O8—C21—O7—Mn2−4.6 (2)C40—C32—C31—C30−1.9 (4)
C22—C21—O7—Mn2174.50 (16)C33—C32—C31—C30177.9 (3)
O5—Mn2—O7—C21−85.47 (14)C7—C8—C9—C10−0.8 (4)
O12i—Mn2—O7—C21177.67 (14)N2—C10—C9—C80.8 (4)
N5—Mn2—O7—C219.4 (2)C3—C4—C5—C6−174.7 (3)
N6—Mn2—O7—C2195.77 (14)C12—C4—C5—C61.9 (4)
O8—Mn2—O7—C212.41 (12)C39—C35—C34—C33−0.6 (5)
C18—C17—C16—C150.9 (3)C36—C35—C34—C33180.0 (3)
C18—C17—C16—N3−179.89 (19)C4—C5—C6—C7−0.3 (4)
C14—C15—C16—C17−0.2 (3)C8—C7—C6—C5175.1 (3)
C14—C15—C16—N3−179.34 (19)C11—C7—C6—C5−2.3 (4)
Mn1—O2—C13—O1−3.4 (2)C35—C34—C33—C32−1.9 (5)
Mn1—O2—C13—C14177.14 (17)C31—C32—C33—C34−177.7 (3)
Mn1—O1—C13—O23.4 (2)C40—C32—C33—C342.1 (4)
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1iii0.932.503.267 (4)140
C10—H10···O2iv0.932.543.210 (3)129
C29—H29···O50.932.513.079 (3)119
C31—H31···O3v0.932.382.888 (4)114
C38—H38···O7vi0.932.453.121 (3)129
C38—H38···O12vii0.932.603.351 (3)139
Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) x, y+1, z; (vi) −x−1, −y, −z; (vii) −x, −y, −z.
Table 1
Selected geometric parameters (Å) top
Mn1—O6i2.1498 (15)Mn2—O52.1608 (15)
Mn1—O112.1508 (15)Mn2—O12ii2.1652 (15)
Mn1—N22.2531 (18)Mn2—O72.1938 (16)
Mn1—N12.2584 (18)Mn2—N52.2411 (18)
Mn1—O12.2661 (15)Mn2—N62.2697 (19)
Mn1—O22.2879 (15)Mn2—O82.3830 (16)
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1iii0.932.503.267 (4)140
C10—H10···O2iv0.932.543.210 (3)129
C29—H29···O50.932.513.079 (3)119
C31—H31···O3v0.932.382.888 (4)114
C38—H38···O7vi0.932.453.121 (3)129
C38—H38···O12vii0.932.603.351 (3)139
Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) x, y+1, z; (vi) −x−1, −y, −z; (vii) −x, −y, −z.
references
References top

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He, H.-Y., Zhou, Y.-L. & Zhu, L.-G. (2004). Acta Cryst. C60, m569–m571.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Sun, D., Cao, R., Sun, Y., Li, X., Bi, W., Hong, M. & Zhao, Y. (2003). Eur. J. Inorg. Chem. pp. 94–98.

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