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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1692–m1693.
Published online 2009 November 28. doi:  10.1107/S1600536809050314
PMCID: PMC2971881

Chlorido{4,4′,6,6′-tetra-tert-butyl-2,2′-[o-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato-κ4 O,N,N′,O′}manganese(III)

Abstract

The asymmetric unit of the title Schiff base complex, [Mn(C36H46N2O2)Cl], comprises two crystallographically independent mol­ecules. The MnIII centre in each mol­ecule adopts a distorted square-pyramidal geometry. Each MnIII ion is coordinated by the N2O2 atoms of the tetra­dentate Schiff base ligand forming the basal plane and the coordinated chloride anion occupies the apical position. Four bifurcated intra­molecular C—H(...)O contacts stabilize the mol­ecular structure. In the crystal packing, mol­ecules are linked into dimers via inter­molecular C—H(...)Cl contacts and further stabilized by C—H(...)π inter­actions. The crystal studied was a non-merohedral twin, the refined ratio of the twin components being 0.441 (1):0.559 (1).

Related literature

For biological applications of Schiff base derivatives, see: Dixit & Srinivasan (1988 [triangle]); Glatzel et al. (2004 [triangle]); Lu et al. (2006 [triangle]); Stallings et al. (1985 [triangle]). For a related structure, see: Eltayeb et al. (2007 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1692-scheme1.jpg

Experimental

Crystal data

  • [Mn(C36H46N2O2)Cl]
  • M r = 629.14
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1692-efi1.jpg
  • a = 10.7650 (6) Å
  • b = 16.8997 (9) Å
  • c = 20.2324 (11) Å
  • α = 107.357 (3)°
  • β = 90.010 (3)°
  • γ = 107.294 (3)°
  • V = 3338.4 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.51 mm−1
  • T = 100 K
  • 0.40 × 0.32 × 0.14 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.822, T max = 0.931
  • 15265 measured reflections
  • 15265 independent reflections
  • 12633 reflections with I > 2σ(I)

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.128
  • S = 1.07
  • 15265 reflections
  • 764 parameters
  • H-atom parameters constrained
  • Δρmax = 0.90 e Å−3
  • Δρmin = −0.87 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050314/tk2582sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050314/tk2582Isup2.hkl

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

Acknowledgments

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia (USM) for the E-Science Fund research grant (PKIMIA/613308) and facilities. The International University of Africa (Sudan) is acknowledged for providing study leave to NEE. HKF and CSY thank USM for the Research University Golden Goose grant No. 1001/PFIZIK/811012. CSY thanks USM for the award of a USM Fellowship.

supplementary crystallographic information

Comment

Manganese complexes with Schiff base ligands have attracted considerable interest in the past decades and recently, due to their variety of applications in chemistry, biology, physics and advanced materials. It had been used as a model for the oxygen-evolving complex of photosystem II (Glatzel et al., 2004), catalysis (Dixit & Srinivasan, 1988), single-molecule magnet (Lu et al., 2006), and it serves as a model for the active sites of manganese-containing metal enzymes (Stallings et al., 1985). Previously, we reported the crystal structure of (ethanol-κO){4,4',6,6'-tetra-tert-butyl-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato-κ4O,O',N,N'}zinc(II) ethanol solvate (Eltayeb et al., 2007). Herein, we report the crystal structure of chlorido{4,4',6,6'-tetra-tert-butyl-2,2'-[o-phenylenebis(nitrilomethylidyne)]diphenolato-κ4O,O',N,N'}manganese(III).

The asymmetric unit of title compound consists of two crystallographically independent molecules, A and B. The MnIII ion in each molecule adopts a distorted square-pyramidal geometry which is coordinated by the N2O2 atoms of the tetradentate Schiff base ligand. The apex position is occupied by a chloride ion. The Mn1 ions in molecules A and B are displaced by 0.3388 (4) and 0.3351 (4) Å out of the mean N1/N2/O1/O2 basal planes towards the axial Cl1 atoms, respectively. The dihedral angles between the central benzene ring (C8–C13) and the other two benzene rings (C1–C6 and C15–C20) are 8.84 (14) and 5.02 (13)° for molecule A, respectively, whereas these angles are 9.74 (14) and 9.35 (14)°, respectively, in molecule B. The geometric parameters are comparable to the previously reported structure (Eltayeb et al., 2007).

Four bifurcated intramolecular C—H···O hydrogen bonds stabilized the molecular structure (Table 1). In the crystal packing (Fig. 2), the molecules are linked into dimers via intermolecular C7A—H7A···Cl1B and C14B—H14B···Cl1A contacts and are further stabilized by C—H···π interactions (Table 1).

Experimental

A sample of 3,5-di-tert-butyl-2-hydroxybenzaldehyde (0.936 g, 4 mmol) was added to a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for half an hour. Then (0.394 g, 2 mmol) manganese chloride tetrahydrate in ethanol (10 ml) was added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was refluxed at room temperature for 3 h. A brown precipitate was obtained, washed with ethanol (5 ml), dried, and then washed by copious amount of diethyl ether. Brown crystals were formed after three days of slow evaporation of diethyl ether solution of the complex held at room temperature.

Refinement

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 or 0.96 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). The rotating group model was applied for the methyl groups. The crystal studied was a non-merohedral twin with a refined BASF of 0.441 (1).

Figures

Fig. 1.
The molecular structure of the two independent molecules in title compound with 50% probability ellipsoids for non-H atoms.
Fig. 2.
The crystal packing in the title compound, viewed down the b axis, showing the molecules are linked into dimers. Intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

[Mn(C36H46N2O2)Cl]Z = 4
Mr = 629.14F(000) = 1336
Triclinic, P1Dx = 1.252 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7650 (6) ÅCell parameters from 9816 reflections
b = 16.8997 (9) Åθ = 2.1–30.4°
c = 20.2324 (11) ŵ = 0.51 mm1
α = 107.357 (3)°T = 100 K
β = 90.010 (3)°Block, brown
γ = 107.294 (3)°0.40 × 0.32 × 0.14 mm
V = 3338.4 (3) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer15265 independent reflections
Radiation source: fine-focus sealed tube12633 reflections with I > 2σ(I)
graphiteRint = 0.000
[var phi] and ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −13→13
Tmin = 0.822, Tmax = 0.931k = −21→20
15265 measured reflectionsl = 0→26

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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0506P)2 + 1.5837P] where P = (Fo2 + 2Fc2)/3
15265 reflections(Δ/σ)max = 0.001
764 parametersΔρmax = 0.90 e Å3
0 restraintsΔρmin = −0.87 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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
Mn1A0.31388 (4)0.14087 (2)0.51808 (2)0.01188 (10)
Cl1A0.18695 (6)0.14030 (4)0.42229 (4)0.01801 (14)
O1A0.25814 (18)0.21411 (11)0.59235 (10)0.0164 (4)
O2A0.47129 (17)0.22959 (11)0.52533 (10)0.0146 (4)
N1A0.1949 (2)0.03602 (13)0.53648 (12)0.0132 (5)
N2A0.3938 (2)0.05414 (13)0.46243 (11)0.0118 (4)
C1A0.1616 (2)0.19866 (17)0.63162 (14)0.0135 (5)
C2A0.1319 (3)0.26952 (17)0.67985 (15)0.0154 (5)
C3A0.0328 (3)0.24975 (18)0.72168 (15)0.0175 (6)
H3A0.01370.29620.75320.021*
C4A−0.0414 (3)0.16473 (18)0.72024 (14)0.0158 (6)
C5A−0.0135 (3)0.09720 (18)0.67274 (14)0.0158 (6)
H5A−0.06080.04020.66970.019*
C6A0.0862 (3)0.11232 (17)0.62797 (14)0.0135 (5)
C7A0.1090 (2)0.03709 (17)0.58203 (14)0.0151 (5)
H7A0.0577−0.01670.58470.018*
C8A0.2104 (2)−0.04378 (16)0.49332 (14)0.0131 (5)
C9A0.1259 (2)−0.12690 (17)0.48770 (14)0.0153 (5)
H9A0.0521−0.13340.51200.018*
C10A0.1536 (3)−0.19873 (17)0.44564 (15)0.0174 (6)
H10A0.0984−0.25420.44200.021*
C11A0.2627 (3)−0.18983 (17)0.40853 (15)0.0173 (6)
H11A0.2799−0.23930.38040.021*
C12A0.3460 (3)−0.10768 (17)0.41325 (15)0.0159 (6)
H12A0.4196−0.10180.38880.019*
C13A0.3184 (2)−0.03402 (16)0.45504 (13)0.0118 (5)
C14A0.4975 (2)0.07412 (16)0.42955 (14)0.0126 (5)
H14A0.51980.02760.40000.015*
C15A0.5796 (2)0.15909 (16)0.43410 (14)0.0130 (5)
C16A0.6860 (2)0.16599 (17)0.39256 (14)0.0131 (5)
H16A0.69570.11550.36160.016*
C17A0.7752 (3)0.24511 (17)0.39671 (14)0.0143 (5)
C18A0.7531 (3)0.31927 (16)0.44348 (14)0.0146 (5)
H18A0.81030.37360.44540.018*
C19A0.6538 (3)0.31784 (17)0.48650 (15)0.0144 (5)
C20A0.5635 (2)0.23477 (16)0.48243 (14)0.0126 (5)
C21A0.2087 (3)0.36459 (17)0.68473 (16)0.0199 (6)
C22A0.1602 (3)0.42991 (19)0.74011 (19)0.0332 (8)
H22A0.17460.42380.78490.050*
H22B0.06850.41860.72930.050*
H22C0.20720.48820.74080.050*
C23A0.3546 (3)0.38322 (18)0.70484 (16)0.0235 (6)
H23A0.38810.34440.67000.035*
H23B0.36540.37440.74890.035*
H23C0.40150.44250.70810.035*
C24A0.1903 (3)0.38074 (18)0.61482 (17)0.0240 (6)
H24A0.21340.33790.57820.036*
H24B0.24550.43800.61710.036*
H24C0.10070.37640.60560.036*
C25A−0.1421 (3)0.14974 (19)0.77303 (15)0.0195 (6)
C26A−0.0728 (3)0.1542 (3)0.83987 (17)0.0341 (4)
H26A−0.02810.11110.83010.051*
H26B−0.13570.14300.87220.051*
H26C−0.01070.21120.85960.051*
C27A−0.2465 (3)0.0606 (2)0.7452 (2)0.0350 (8)
H27A−0.20660.01550.73920.053*
H27B−0.28740.05530.70120.053*
H27C−0.31110.05510.77760.053*
C28A−0.2122 (3)0.2194 (2)0.78932 (19)0.0300 (7)
H28A−0.15000.27580.81120.045*
H28B−0.27790.20680.82010.045*
H28C−0.25270.21900.74690.045*
C29A0.6423 (3)0.40175 (17)0.53913 (15)0.0171 (6)
C30A0.7391 (3)0.48344 (18)0.52845 (19)0.0313 (8)
H30A0.72570.53470.55990.047*
H30B0.72510.48290.48140.047*
H30C0.82690.48380.53730.047*
C31A0.5041 (3)0.40935 (17)0.53201 (15)0.0194 (6)
H31A0.49930.46150.56630.029*
H31B0.44100.35950.53900.029*
H31C0.48580.41180.48630.029*
C32A0.6727 (3)0.40166 (19)0.61313 (16)0.0235 (7)
H32A0.66560.45400.64610.035*
H32B0.75990.39900.61840.035*
H32C0.61160.35190.62130.035*
C33A0.8967 (3)0.25655 (17)0.35688 (15)0.0168 (6)
C34A0.8929 (3)0.3135 (2)0.30992 (17)0.0341 (4)
H34A0.88740.36900.33810.051*
H34B0.81800.28480.27620.051*
H34C0.97100.32210.28640.051*
C35A0.9076 (3)0.16952 (18)0.31127 (16)0.0210 (6)
H35A0.90850.13300.33950.031*
H35B0.98700.17940.28900.031*
H35C0.83420.14140.27650.031*
C36A1.0181 (3)0.30190 (18)0.40908 (16)0.0225 (6)
H36A1.02280.26600.43730.034*
H36B1.01310.35710.43820.034*
H36C1.09470.31120.38450.034*
Mn1B0.81404 (4)0.14792 (2)0.05624 (2)0.01257 (10)
Cl1B0.67345 (6)0.13879 (4)0.14576 (4)0.01833 (14)
O1B0.96506 (17)0.24070 (11)0.09672 (10)0.0159 (4)
O2B0.75671 (18)0.21918 (12)0.01644 (10)0.0179 (4)
N1B0.8995 (2)0.06442 (14)0.07023 (12)0.0134 (5)
N2B0.7023 (2)0.04165 (13)−0.01512 (12)0.0137 (5)
C1B1.0666 (3)0.24648 (17)0.13647 (14)0.0137 (5)
C2B1.1640 (3)0.32922 (17)0.16545 (14)0.0149 (6)
C3B1.2674 (3)0.33187 (17)0.20758 (14)0.0160 (6)
H3B1.32960.38590.22810.019*
C4B1.2860 (3)0.25854 (17)0.22202 (14)0.0145 (5)
C5B1.1941 (3)0.18003 (17)0.19211 (14)0.0148 (5)
H5B1.20320.13060.20020.018*
C6B1.0843 (2)0.17193 (17)0.14869 (14)0.0135 (5)
C7B1.0020 (3)0.08618 (17)0.11369 (14)0.0146 (5)
H7B1.02350.04080.12280.018*
C8B0.8300 (2)−0.02452 (16)0.03402 (14)0.0139 (5)
C9B0.8616 (3)−0.09657 (17)0.03990 (15)0.0160 (6)
H9B0.9347−0.08860.06860.019*
C10B0.7843 (3)−0.17947 (17)0.00308 (14)0.0169 (6)
H10B0.8062−0.22740.00660.020*
C11B0.6740 (3)−0.19231 (17)−0.03922 (15)0.0170 (6)
H11B0.6207−0.2486−0.06250.020*
C12B0.6431 (3)−0.12087 (17)−0.04682 (14)0.0161 (6)
H12B0.5700−0.1293−0.07570.019*
C13B0.7222 (3)−0.03696 (17)−0.01096 (14)0.0148 (5)
C14B0.6164 (2)0.04058 (17)−0.06111 (14)0.0135 (5)
H14B0.5681−0.0137−0.09110.016*
C15B0.5893 (3)0.11481 (17)−0.06973 (14)0.0146 (5)
C16B0.4907 (3)0.09798 (17)−0.12289 (14)0.0156 (5)
H16B0.44660.0406−0.14900.019*
C17B0.4587 (3)0.16487 (18)−0.13671 (14)0.0161 (6)
C18B0.5239 (3)0.25035 (17)−0.09345 (14)0.0157 (6)
H18B0.50090.2958−0.10150.019*
C19B0.6198 (3)0.27152 (17)−0.03982 (15)0.0147 (5)
C20B0.6577 (2)0.20141 (17)−0.02949 (14)0.0149 (5)
C21B1.1547 (3)0.41047 (17)0.14861 (15)0.0170 (6)
C22B1.2720 (3)0.49113 (17)0.18278 (16)0.0246 (7)
H22D1.35080.48050.16590.037*
H22E1.27700.50320.23230.037*
H22F1.26190.54030.17150.037*
C23B1.0298 (3)0.43111 (19)0.17463 (17)0.0238 (6)
H23D1.03370.44400.22430.036*
H23E0.95480.38160.15330.036*
H23F1.02320.48060.16250.036*
C24B1.1539 (3)0.39474 (17)0.07001 (15)0.0186 (6)
H24D1.23500.38630.05500.028*
H24E1.14360.44430.05950.028*
H24F1.08270.34370.04630.028*
C25B1.4080 (3)0.27108 (17)0.26781 (15)0.0162 (6)
C26B1.4039 (3)0.3293 (2)0.34077 (17)0.0341 (4)
H26D1.33050.30070.36120.051*
H26E1.39540.38340.33850.051*
H26F1.48320.34060.36870.051*
C27B1.5314 (3)0.31503 (19)0.23714 (16)0.0218 (6)
H27D1.53550.27800.19140.033*
H27E1.60780.32440.26650.033*
H27F1.52750.37000.23450.033*
C28B1.4175 (3)0.18426 (18)0.27298 (16)0.0197 (6)
H28D1.41990.14640.22730.030*
H28E1.34270.15720.29340.030*
H28F1.49570.19490.30150.030*
C29B0.6846 (3)0.36594 (17)0.00566 (16)0.0170 (6)
C30B0.6189 (3)0.42843 (18)−0.01036 (17)0.0229 (6)
H30D0.52770.4100−0.00380.034*
H30E0.62840.4278−0.05770.034*
H30F0.65950.48650.02040.034*
C31B0.8295 (3)0.39528 (18)−0.00812 (17)0.0241 (7)
H31D0.87180.35610.00030.036*
H31E0.87190.45320.02240.036*
H31F0.83510.3948−0.05560.036*
C32B0.6733 (3)0.37385 (18)0.08280 (16)0.0227 (6)
H32D0.58290.36050.09150.034*
H32E0.72010.43230.11090.034*
H32F0.70970.33370.09430.034*
C33B0.3620 (3)0.15007 (19)−0.19793 (15)0.0201 (6)
C34B0.4377 (3)0.1670 (3)−0.25857 (17)0.0341 (4)
H34D0.48920.1282−0.27180.051*
H34E0.49420.2263−0.24480.051*
H34F0.37750.1573−0.29730.051*
C35B0.2673 (4)0.0572 (2)−0.2201 (2)0.0399 (9)
H35D0.31490.0165−0.23670.060*
H35E0.20420.0506−0.25650.060*
H35F0.22310.0462−0.18100.060*
C36B0.2804 (3)0.2125 (2)−0.17889 (17)0.0254 (7)
H36D0.21820.2000−0.21750.038*
H36E0.33680.2716−0.16790.038*
H36F0.23490.2051−0.13930.038*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn1A0.01029 (19)0.00976 (18)0.0144 (2)0.00330 (14)0.00419 (16)0.00183 (16)
Cl1A0.0143 (3)0.0197 (3)0.0216 (4)0.0054 (2)0.0015 (3)0.0087 (3)
O1A0.0166 (9)0.0130 (9)0.0185 (10)0.0051 (7)0.0093 (8)0.0029 (8)
O2A0.0113 (9)0.0124 (9)0.0164 (10)0.0021 (7)0.0060 (8)0.0008 (7)
N1A0.0113 (10)0.0128 (10)0.0155 (12)0.0046 (8)0.0021 (9)0.0038 (9)
N2A0.0114 (10)0.0098 (10)0.0133 (11)0.0038 (8)0.0014 (9)0.0018 (8)
C1A0.0128 (13)0.0166 (13)0.0113 (13)0.0058 (10)0.0034 (10)0.0036 (10)
C2A0.0136 (12)0.0167 (13)0.0145 (13)0.0066 (10)0.0011 (11)0.0012 (11)
C3A0.0135 (13)0.0246 (14)0.0157 (14)0.0103 (11)0.0022 (11)0.0039 (11)
C4A0.0107 (12)0.0253 (14)0.0139 (14)0.0081 (11)0.0037 (11)0.0073 (11)
C5A0.0119 (12)0.0198 (13)0.0147 (14)0.0037 (10)0.0008 (11)0.0052 (11)
C6A0.0123 (12)0.0158 (13)0.0137 (13)0.0061 (10)0.0024 (11)0.0048 (11)
C7A0.0111 (12)0.0177 (13)0.0169 (14)0.0046 (10)0.0014 (11)0.0058 (11)
C8A0.0115 (12)0.0146 (12)0.0130 (13)0.0039 (10)−0.0009 (10)0.0039 (10)
C9A0.0087 (12)0.0190 (13)0.0166 (14)0.0013 (10)0.0009 (11)0.0064 (11)
C10A0.0182 (14)0.0131 (12)0.0211 (15)0.0026 (10)−0.0015 (11)0.0078 (11)
C11A0.0207 (14)0.0111 (12)0.0178 (14)0.0066 (10)−0.0014 (11)−0.0005 (10)
C12A0.0135 (13)0.0152 (13)0.0183 (14)0.0047 (10)0.0009 (11)0.0043 (11)
C13A0.0112 (12)0.0117 (12)0.0113 (13)0.0033 (9)0.0008 (10)0.0023 (10)
C14A0.0083 (12)0.0124 (12)0.0150 (13)0.0044 (9)0.0010 (10)0.0001 (10)
C15A0.0106 (12)0.0108 (12)0.0154 (13)0.0031 (10)−0.0001 (10)0.0013 (10)
C16A0.0113 (12)0.0160 (12)0.0116 (13)0.0057 (10)0.0024 (10)0.0025 (10)
C17A0.0116 (12)0.0173 (13)0.0146 (13)0.0050 (10)0.0031 (10)0.0054 (10)
C18A0.0137 (12)0.0110 (12)0.0169 (13)−0.0005 (10)0.0016 (11)0.0054 (10)
C19A0.0124 (12)0.0135 (12)0.0166 (14)0.0045 (10)0.0021 (11)0.0032 (11)
C20A0.0106 (12)0.0146 (12)0.0137 (13)0.0056 (10)0.0009 (10)0.0043 (10)
C21A0.0226 (15)0.0139 (13)0.0216 (15)0.0076 (11)0.0082 (12)0.0014 (11)
C22A0.0351 (18)0.0195 (15)0.039 (2)0.0091 (13)0.0176 (16)−0.0001 (14)
C23A0.0228 (15)0.0180 (14)0.0227 (16)0.0022 (11)0.0012 (13)0.0002 (12)
C24A0.0231 (15)0.0192 (14)0.0295 (17)0.0058 (12)0.0025 (13)0.0082 (13)
C25A0.0124 (13)0.0319 (15)0.0176 (15)0.0092 (11)0.0075 (12)0.0104 (13)
C26A0.0249 (8)0.0606 (11)0.0232 (8)0.0190 (8)0.0054 (8)0.0165 (9)
C27A0.0336 (18)0.0309 (17)0.043 (2)0.0093 (14)0.0251 (16)0.0162 (16)
C28A0.0257 (16)0.0282 (16)0.0359 (19)0.0105 (13)0.0148 (15)0.0076 (15)
C29A0.0164 (13)0.0121 (12)0.0199 (14)0.0022 (10)0.0023 (11)0.0031 (11)
C30A0.0295 (17)0.0122 (13)0.047 (2)0.0046 (12)0.0157 (15)0.0042 (14)
C31A0.0235 (15)0.0129 (13)0.0221 (15)0.0089 (11)0.0046 (12)0.0031 (11)
C32A0.0228 (15)0.0215 (14)0.0234 (16)0.0115 (12)−0.0036 (13)−0.0016 (12)
C33A0.0141 (13)0.0183 (13)0.0194 (14)0.0056 (10)0.0069 (11)0.0074 (11)
C34A0.0249 (8)0.0606 (11)0.0232 (8)0.0190 (8)0.0054 (8)0.0165 (9)
C35A0.0173 (14)0.0215 (14)0.0202 (15)0.0059 (11)0.0088 (12)0.0010 (12)
C36A0.0153 (14)0.0200 (14)0.0279 (16)0.0038 (11)0.0029 (12)0.0029 (12)
Mn1B0.01071 (19)0.01110 (19)0.0154 (2)0.00394 (15)−0.00031 (17)0.00292 (16)
Cl1B0.0148 (3)0.0195 (3)0.0186 (3)0.0058 (2)0.0037 (3)0.0023 (3)
O1B0.0118 (9)0.0131 (9)0.0221 (10)0.0036 (7)−0.0008 (8)0.0047 (8)
O2B0.0177 (10)0.0150 (9)0.0204 (11)0.0049 (8)−0.0052 (8)0.0048 (8)
N1B0.0120 (11)0.0129 (10)0.0149 (11)0.0042 (8)0.0023 (9)0.0036 (9)
N2B0.0121 (10)0.0129 (10)0.0168 (12)0.0054 (8)0.0034 (9)0.0041 (9)
C1B0.0136 (13)0.0147 (12)0.0131 (13)0.0069 (10)0.0023 (11)0.0023 (10)
C2B0.0154 (13)0.0146 (13)0.0146 (13)0.0073 (10)0.0027 (11)0.0021 (11)
C3B0.0152 (13)0.0148 (12)0.0156 (14)0.0040 (10)0.0029 (11)0.0020 (10)
C4B0.0136 (12)0.0185 (13)0.0118 (13)0.0067 (10)0.0027 (10)0.0038 (10)
C5B0.0156 (13)0.0181 (13)0.0149 (14)0.0092 (10)0.0055 (11)0.0071 (11)
C6B0.0094 (12)0.0165 (13)0.0145 (13)0.0029 (10)0.0037 (10)0.0056 (11)
C7B0.0147 (13)0.0156 (13)0.0171 (14)0.0074 (10)0.0066 (11)0.0075 (11)
C8B0.0118 (12)0.0145 (12)0.0137 (13)0.0035 (10)0.0033 (10)0.0025 (10)
C9B0.0166 (13)0.0146 (13)0.0172 (14)0.0066 (10)0.0010 (11)0.0036 (11)
C10B0.0212 (14)0.0144 (13)0.0172 (14)0.0085 (11)0.0049 (11)0.0053 (11)
C11B0.0178 (13)0.0142 (12)0.0182 (14)0.0048 (10)0.0063 (11)0.0040 (11)
C12B0.0136 (13)0.0173 (13)0.0135 (13)0.0041 (10)0.0040 (11)−0.0004 (11)
C13B0.0137 (13)0.0157 (12)0.0167 (14)0.0064 (10)0.0058 (11)0.0056 (10)
C14B0.0134 (12)0.0150 (12)0.0107 (13)0.0049 (10)0.0025 (10)0.0016 (10)
C15B0.0131 (13)0.0180 (13)0.0117 (13)0.0047 (10)0.0016 (11)0.0036 (11)
C16B0.0134 (13)0.0172 (13)0.0135 (13)0.0051 (10)0.0026 (11)0.0008 (11)
C17B0.0136 (13)0.0237 (14)0.0128 (13)0.0095 (11)0.0045 (11)0.0047 (11)
C18B0.0155 (13)0.0190 (13)0.0176 (14)0.0106 (11)0.0060 (11)0.0080 (11)
C19B0.0138 (13)0.0164 (13)0.0152 (14)0.0064 (10)0.0033 (11)0.0053 (11)
C20B0.0101 (12)0.0208 (13)0.0142 (14)0.0054 (10)0.0028 (11)0.0058 (11)
C21B0.0199 (14)0.0118 (12)0.0205 (14)0.0065 (10)0.0002 (11)0.0052 (11)
C22B0.0305 (16)0.0140 (13)0.0251 (16)0.0037 (12)−0.0059 (13)0.0032 (12)
C23B0.0282 (16)0.0189 (14)0.0274 (16)0.0134 (12)0.0059 (13)0.0055 (12)
C24B0.0204 (14)0.0139 (13)0.0217 (15)0.0043 (10)0.0007 (12)0.0069 (11)
C25B0.0133 (13)0.0185 (13)0.0168 (14)0.0068 (10)−0.0014 (11)0.0037 (11)
C26B0.0249 (8)0.0606 (11)0.0232 (8)0.0190 (8)0.0054 (8)0.0165 (9)
C27B0.0138 (13)0.0247 (15)0.0269 (16)0.0054 (11)0.0007 (12)0.0088 (12)
C28B0.0138 (13)0.0227 (14)0.0219 (15)0.0066 (11)−0.0025 (12)0.0050 (12)
C29B0.0151 (13)0.0150 (13)0.0222 (15)0.0061 (10)−0.0005 (11)0.0062 (11)
C30B0.0221 (15)0.0182 (14)0.0290 (17)0.0062 (11)−0.0012 (13)0.0083 (12)
C31B0.0194 (14)0.0200 (14)0.0332 (18)0.0042 (11)−0.0012 (13)0.0107 (13)
C32B0.0262 (15)0.0181 (14)0.0223 (16)0.0078 (12)0.0004 (13)0.0032 (12)
C33B0.0164 (14)0.0296 (15)0.0172 (15)0.0117 (12)0.0001 (12)0.0068 (12)
C34B0.0249 (8)0.0606 (11)0.0232 (8)0.0190 (8)0.0054 (8)0.0165 (9)
C35B0.041 (2)0.0268 (17)0.045 (2)0.0068 (15)−0.0263 (18)0.0041 (16)
C36B0.0183 (14)0.0331 (16)0.0287 (17)0.0125 (13)−0.0041 (13)0.0108 (14)

Geometric parameters (Å, °)

Mn1A—O1A1.8660 (19)Mn1B—O1B1.8682 (18)
Mn1A—O2A1.8706 (18)Mn1B—O2B1.8710 (19)
Mn1A—N2A1.980 (2)Mn1B—N2B1.981 (2)
Mn1A—N1A1.991 (2)Mn1B—N1B1.982 (2)
Mn1A—Cl1A2.3671 (8)Mn1B—Cl1B2.3714 (8)
O1A—C1A1.320 (3)O1B—C1B1.319 (3)
O2A—C20A1.319 (3)O2B—C20B1.316 (3)
N1A—C7A1.305 (4)N1B—C7B1.300 (3)
N1A—C8A1.429 (3)N1B—C8B1.425 (3)
N2A—C14A1.309 (3)N2B—C14B1.305 (3)
N2A—C13A1.431 (3)N2B—C13B1.433 (3)
C1A—C2A1.421 (4)C1B—C6B1.419 (4)
C1A—C6A1.423 (4)C1B—C2B1.427 (4)
C2A—C3A1.387 (4)C2B—C3B1.383 (4)
C2A—C21A1.546 (4)C2B—C21B1.540 (4)
C3A—C4A1.413 (4)C3B—C4B1.423 (4)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.366 (4)C4B—C5B1.358 (4)
C4A—C25A1.542 (4)C4B—C25B1.532 (4)
C5A—C6A1.419 (4)C5B—C6B1.421 (4)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.422 (4)C6B—C7B1.418 (4)
C7A—H7A0.9300C7B—H7B0.9300
C8A—C13A1.393 (4)C8B—C9B1.395 (4)
C8A—C9A1.400 (3)C8B—C13B1.400 (4)
C9A—C10A1.373 (4)C9B—C10B1.376 (4)
C9A—H9A0.9300C9B—H9B0.9300
C10A—C11A1.388 (4)C10B—C11B1.387 (4)
C10A—H10A0.9300C10B—H10B0.9300
C11A—C12A1.387 (4)C11B—C12B1.393 (4)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.395 (4)C12B—C13B1.389 (4)
C12A—H12A0.9300C12B—H12B0.9300
C14A—C15A1.421 (3)C14B—C15B1.427 (4)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C20A1.417 (3)C15B—C20B1.412 (4)
C15A—C16A1.418 (4)C15B—C16B1.415 (4)
C16A—C17A1.373 (4)C16B—C17B1.376 (4)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.411 (4)C17B—C18B1.410 (4)
C17A—C33A1.531 (4)C17B—C33B1.530 (4)
C18A—C19A1.378 (4)C18B—C19B1.385 (4)
C18A—H18A0.9300C18B—H18B0.9300
C19A—C20A1.429 (4)C19B—C20B1.431 (4)
C19A—C29A1.537 (4)C19B—C29B1.530 (4)
C21A—C22A1.533 (4)C21B—C22B1.531 (4)
C21A—C23A1.537 (4)C21B—C24B1.532 (4)
C21A—C24A1.541 (4)C21B—C23B1.542 (4)
C22A—H22A0.9600C22B—H22D0.9600
C22A—H22B0.9600C22B—H22E0.9600
C22A—H22C0.9600C22B—H22F0.9600
C23A—H23A0.9600C23B—H23D0.9600
C23A—H23B0.9600C23B—H23E0.9600
C23A—H23C0.9600C23B—H23F0.9600
C24A—H24A0.9600C24B—H24D0.9600
C24A—H24B0.9600C24B—H24E0.9600
C24A—H24C0.9600C24B—H24F0.9600
C25A—C26A1.515 (4)C25B—C26B1.519 (4)
C25A—C27A1.529 (4)C25B—C28B1.535 (4)
C25A—C28A1.536 (4)C25B—C27B1.546 (4)
C26A—H26A0.9600C26B—H26D0.9600
C26A—H26B0.9600C26B—H26E0.9600
C26A—H26C0.9600C26B—H26F0.9600
C27A—H27A0.9600C27B—H27D0.9600
C27A—H27B0.9600C27B—H27E0.9600
C27A—H27C0.9600C27B—H27F0.9600
C28A—H28A0.9600C28B—H28D0.9600
C28A—H28B0.9600C28B—H28E0.9600
C28A—H28C0.9600C28B—H28F0.9600
C29A—C32A1.533 (4)C29B—C32B1.534 (4)
C29A—C30A1.537 (4)C29B—C30B1.539 (4)
C29A—C31A1.542 (4)C29B—C31B1.543 (4)
C30A—H30A0.9600C30B—H30D0.9600
C30A—H30B0.9600C30B—H30E0.9600
C30A—H30C0.9600C30B—H30F0.9600
C31A—H31A0.9600C31B—H31D0.9600
C31A—H31B0.9600C31B—H31E0.9600
C31A—H31C0.9600C31B—H31F0.9600
C32A—H32A0.9600C32B—H32D0.9600
C32A—H32B0.9600C32B—H32E0.9600
C32A—H32C0.9600C32B—H32F0.9600
C33A—C35A1.523 (4)C33B—C34B1.524 (4)
C33A—C36A1.527 (4)C33B—C35B1.527 (4)
C33A—C34A1.550 (4)C33B—C36B1.531 (4)
C34A—H34A0.9600C34B—H34D0.9600
C34A—H34B0.9600C34B—H34E0.9600
C34A—H34C0.9600C34B—H34F0.9600
C35A—H35A0.9600C35B—H35D0.9600
C35A—H35B0.9600C35B—H35E0.9600
C35A—H35C0.9600C35B—H35F0.9600
C36A—H36A0.9600C36B—H36D0.9600
C36A—H36B0.9600C36B—H36E0.9600
C36A—H36C0.9600C36B—H36F0.9600
O1A—Mn1A—O2A90.39 (8)O1B—Mn1B—O2B89.77 (8)
O1A—Mn1A—N2A162.68 (9)O1B—Mn1B—N2B157.14 (9)
O2A—Mn1A—N2A89.72 (8)O2B—Mn1B—N2B91.08 (8)
O1A—Mn1A—N1A90.80 (9)O1B—Mn1B—N1B90.30 (8)
O2A—Mn1A—N1A155.86 (9)O2B—Mn1B—N1B161.87 (9)
N2A—Mn1A—N1A82.16 (9)N2B—Mn1B—N1B81.95 (9)
O1A—Mn1A—Cl1A101.53 (6)O1B—Mn1B—Cl1B106.37 (7)
O2A—Mn1A—Cl1A104.82 (6)O2B—Mn1B—Cl1B101.50 (7)
N2A—Mn1A—Cl1A95.17 (7)N2B—Mn1B—Cl1B95.83 (7)
N1A—Mn1A—Cl1A98.55 (7)N1B—Mn1B—Cl1B95.87 (7)
C1A—O1A—Mn1A132.19 (17)C1B—O1B—Mn1B131.46 (16)
C20A—O2A—Mn1A129.94 (16)C20B—O2B—Mn1B131.52 (17)
C7A—N1A—C8A121.7 (2)C7B—N1B—C8B121.7 (2)
C7A—N1A—Mn1A125.27 (18)C7B—N1B—Mn1B124.13 (18)
C8A—N1A—Mn1A113.01 (17)C8B—N1B—Mn1B113.81 (16)
C14A—N2A—C13A122.8 (2)C14B—N2B—C13B121.8 (2)
C14A—N2A—Mn1A123.68 (17)C14B—N2B—Mn1B124.98 (17)
C13A—N2A—Mn1A113.18 (16)C13B—N2B—Mn1B113.23 (17)
O1A—C1A—C2A119.8 (2)O1B—C1B—C6B121.7 (2)
O1A—C1A—C6A121.9 (2)O1B—C1B—C2B119.1 (2)
C2A—C1A—C6A118.3 (2)C6B—C1B—C2B119.1 (2)
C3A—C2A—C1A117.5 (2)C3B—C2B—C1B116.8 (2)
C3A—C2A—C21A122.1 (2)C3B—C2B—C21B122.3 (2)
C1A—C2A—C21A120.4 (2)C1B—C2B—C21B120.9 (2)
C2A—C3A—C4A125.3 (3)C2B—C3B—C4B125.2 (2)
C2A—C3A—H3A117.3C2B—C3B—H3B117.4
C4A—C3A—H3A117.3C4B—C3B—H3B117.4
C5A—C4A—C3A116.6 (3)C5B—C4B—C3B116.9 (2)
C5A—C4A—C25A122.0 (3)C5B—C4B—C25B123.7 (2)
C3A—C4A—C25A121.3 (2)C3B—C4B—C25B119.3 (2)
C4A—C5A—C6A121.3 (3)C4B—C5B—C6B121.3 (2)
C4A—C5A—H5A119.3C4B—C5B—H5B119.3
C6A—C5A—H5A119.3C6B—C5B—H5B119.3
C5A—C6A—C7A116.4 (2)C7B—C6B—C1B122.2 (2)
C5A—C6A—C1A121.0 (2)C7B—C6B—C5B117.0 (2)
C7A—C6A—C1A122.6 (3)C1B—C6B—C5B120.6 (2)
N1A—C7A—C6A126.5 (3)N1B—C7B—C6B126.7 (2)
N1A—C7A—H7A116.8N1B—C7B—H7B116.6
C6A—C7A—H7A116.8C6B—C7B—H7B116.6
C13A—C8A—C9A120.5 (2)C9B—C8B—C13B119.8 (2)
C13A—C8A—N1A114.9 (2)C9B—C8B—N1B125.6 (2)
C9A—C8A—N1A124.5 (2)C13B—C8B—N1B114.6 (2)
C10A—C9A—C8A118.9 (3)C10B—C9B—C8B119.8 (2)
C10A—C9A—H9A120.6C10B—C9B—H9B120.1
C8A—C9A—H9A120.6C8B—C9B—H9B120.1
C9A—C10A—C11A121.1 (2)C9B—C10B—C11B120.7 (2)
C9A—C10A—H10A119.5C9B—C10B—H10B119.6
C11A—C10A—H10A119.5C11B—C10B—H10B119.6
C12A—C11A—C10A120.4 (2)C10B—C11B—C12B120.0 (2)
C12A—C11A—H11A119.8C10B—C11B—H11B120.0
C10A—C11A—H11A119.8C12B—C11B—H11B120.0
C11A—C12A—C13A119.3 (3)C13B—C12B—C11B119.6 (3)
C11A—C12A—H12A120.3C13B—C12B—H12B120.2
C13A—C12A—H12A120.3C11B—C12B—H12B120.2
C8A—C13A—C12A119.8 (2)C12B—C13B—C8B120.0 (2)
C8A—C13A—N2A115.4 (2)C12B—C13B—N2B125.1 (2)
C12A—C13A—N2A124.8 (2)C8B—C13B—N2B114.9 (2)
N2A—C14A—C15A127.1 (2)N2B—C14B—C15B126.2 (2)
N2A—C14A—H14A116.5N2B—C14B—H14B116.9
C15A—C14A—H14A116.5C15B—C14B—H14B116.9
C20A—C15A—C16A120.3 (2)C20B—C15B—C16B120.4 (2)
C20A—C15A—C14A121.7 (2)C20B—C15B—C14B123.2 (2)
C16A—C15A—C14A117.8 (2)C16B—C15B—C14B116.4 (2)
C17A—C16A—C15A121.9 (2)C17B—C16B—C15B121.3 (2)
C17A—C16A—H16A119.1C17B—C16B—H16B119.4
C15A—C16A—H16A119.1C15B—C16B—H16B119.4
C16A—C17A—C18A116.2 (2)C16B—C17B—C18B117.1 (2)
C16A—C17A—C33A124.4 (2)C16B—C17B—C33B122.9 (2)
C18A—C17A—C33A119.4 (2)C18B—C17B—C33B120.0 (2)
C19A—C18A—C17A125.4 (2)C19B—C18B—C17B124.7 (2)
C19A—C18A—H18A117.3C19B—C18B—H18B117.7
C17A—C18A—H18A117.3C17B—C18B—H18B117.7
C18A—C19A—C20A117.6 (2)C18B—C19B—C20B117.2 (2)
C18A—C19A—C29A121.7 (2)C18B—C19B—C29B121.6 (2)
C20A—C19A—C29A120.6 (2)C20B—C19B—C29B121.3 (2)
O2A—C20A—C15A121.5 (2)O2B—C20B—C15B121.5 (2)
O2A—C20A—C19A119.8 (2)O2B—C20B—C19B119.3 (2)
C15A—C20A—C19A118.6 (2)C15B—C20B—C19B119.2 (2)
C22A—C21A—C23A107.9 (2)C22B—C21B—C24B106.5 (2)
C22A—C21A—C24A107.2 (2)C22B—C21B—C2B112.2 (2)
C23A—C21A—C24A110.0 (3)C24B—C21B—C2B109.8 (2)
C22A—C21A—C2A111.3 (2)C22B—C21B—C23B108.0 (2)
C23A—C21A—C2A110.0 (2)C24B—C21B—C23B110.2 (2)
C24A—C21A—C2A110.5 (2)C2B—C21B—C23B110.0 (2)
C21A—C22A—H22A109.5C21B—C22B—H22D109.5
C21A—C22A—H22B109.5C21B—C22B—H22E109.5
H22A—C22A—H22B109.5H22D—C22B—H22E109.5
C21A—C22A—H22C109.5C21B—C22B—H22F109.5
H22A—C22A—H22C109.5H22D—C22B—H22F109.5
H22B—C22A—H22C109.5H22E—C22B—H22F109.5
C21A—C23A—H23A109.5C21B—C23B—H23D109.5
C21A—C23A—H23B109.5C21B—C23B—H23E109.5
H23A—C23A—H23B109.5H23D—C23B—H23E109.5
C21A—C23A—H23C109.5C21B—C23B—H23F109.5
H23A—C23A—H23C109.5H23D—C23B—H23F109.5
H23B—C23A—H23C109.5H23E—C23B—H23F109.5
C21A—C24A—H24A109.5C21B—C24B—H24D109.5
C21A—C24A—H24B109.5C21B—C24B—H24E109.5
H24A—C24A—H24B109.5H24D—C24B—H24E109.5
C21A—C24A—H24C109.5C21B—C24B—H24F109.5
H24A—C24A—H24C109.5H24D—C24B—H24F109.5
H24B—C24A—H24C109.5H24E—C24B—H24F109.5
C26A—C25A—C27A108.5 (3)C26B—C25B—C4B109.3 (2)
C26A—C25A—C28A108.9 (3)C26B—C25B—C28B108.2 (2)
C27A—C25A—C28A107.5 (2)C4B—C25B—C28B112.1 (2)
C26A—C25A—C4A109.4 (2)C26B—C25B—C27B109.1 (2)
C27A—C25A—C4A111.6 (2)C4B—C25B—C27B109.4 (2)
C28A—C25A—C4A110.9 (2)C28B—C25B—C27B108.6 (2)
C25A—C26A—H26A109.5C25B—C26B—H26D109.5
C25A—C26A—H26B109.5C25B—C26B—H26E109.5
H26A—C26A—H26B109.5H26D—C26B—H26E109.5
C25A—C26A—H26C109.5C25B—C26B—H26F109.5
H26A—C26A—H26C109.5H26D—C26B—H26F109.5
H26B—C26A—H26C109.5H26E—C26B—H26F109.5
C25A—C27A—H27A109.5C25B—C27B—H27D109.5
C25A—C27A—H27B109.5C25B—C27B—H27E109.5
H27A—C27A—H27B109.5H27D—C27B—H27E109.5
C25A—C27A—H27C109.5C25B—C27B—H27F109.5
H27A—C27A—H27C109.5H27D—C27B—H27F109.5
H27B—C27A—H27C109.5H27E—C27B—H27F109.5
C25A—C28A—H28A109.5C25B—C28B—H28D109.5
C25A—C28A—H28B109.5C25B—C28B—H28E109.5
H28A—C28A—H28B109.5H28D—C28B—H28E109.5
C25A—C28A—H28C109.5C25B—C28B—H28F109.5
H28A—C28A—H28C109.5H28D—C28B—H28F109.5
H28B—C28A—H28C109.5H28E—C28B—H28F109.5
C32A—C29A—C30A108.2 (2)C19B—C29B—C32B110.3 (2)
C32A—C29A—C19A109.4 (2)C19B—C29B—C30B111.8 (2)
C30A—C29A—C19A111.4 (2)C32B—C29B—C30B107.0 (2)
C32A—C29A—C31A109.1 (2)C19B—C29B—C31B109.2 (2)
C30A—C29A—C31A107.3 (2)C32B—C29B—C31B110.3 (2)
C19A—C29A—C31A111.4 (2)C30B—C29B—C31B108.1 (2)
C29A—C30A—H30A109.5C29B—C30B—H30D109.5
C29A—C30A—H30B109.5C29B—C30B—H30E109.5
H30A—C30A—H30B109.5H30D—C30B—H30E109.5
C29A—C30A—H30C109.5C29B—C30B—H30F109.5
H30A—C30A—H30C109.5H30D—C30B—H30F109.5
H30B—C30A—H30C109.5H30E—C30B—H30F109.5
C29A—C31A—H31A109.5C29B—C31B—H31D109.5
C29A—C31A—H31B109.5C29B—C31B—H31E109.5
H31A—C31A—H31B109.5H31D—C31B—H31E109.5
C29A—C31A—H31C109.5C29B—C31B—H31F109.5
H31A—C31A—H31C109.5H31D—C31B—H31F109.5
H31B—C31A—H31C109.5H31E—C31B—H31F109.5
C29A—C32A—H32A109.5C29B—C32B—H32D109.5
C29A—C32A—H32B109.5C29B—C32B—H32E109.5
H32A—C32A—H32B109.5H32D—C32B—H32E109.5
C29A—C32A—H32C109.5C29B—C32B—H32F109.5
H32A—C32A—H32C109.5H32D—C32B—H32F109.5
H32B—C32A—H32C109.5H32E—C32B—H32F109.5
C35A—C33A—C36A108.3 (2)C34B—C33B—C35B110.1 (3)
C35A—C33A—C17A112.1 (2)C34B—C33B—C17B109.1 (2)
C36A—C33A—C17A108.9 (2)C35B—C33B—C17B110.9 (2)
C35A—C33A—C34A108.5 (3)C34B—C33B—C36B107.8 (3)
C36A—C33A—C34A109.0 (2)C35B—C33B—C36B107.4 (3)
C17A—C33A—C34A110.0 (2)C17B—C33B—C36B111.4 (2)
C33A—C34A—H34A109.5C33B—C34B—H34D109.5
C33A—C34A—H34B109.5C33B—C34B—H34E109.5
H34A—C34A—H34B109.5H34D—C34B—H34E109.5
C33A—C34A—H34C109.5C33B—C34B—H34F109.5
H34A—C34A—H34C109.5H34D—C34B—H34F109.5
H34B—C34A—H34C109.5H34E—C34B—H34F109.5
C33A—C35A—H35A109.5C33B—C35B—H35D109.5
C33A—C35A—H35B109.5C33B—C35B—H35E109.5
H35A—C35A—H35B109.5H35D—C35B—H35E109.5
C33A—C35A—H35C109.5C33B—C35B—H35F109.5
H35A—C35A—H35C109.5H35D—C35B—H35F109.5
H35B—C35A—H35C109.5H35E—C35B—H35F109.5
C33A—C36A—H36A109.5C33B—C36B—H36D109.5
C33A—C36A—H36B109.5C33B—C36B—H36E109.5
H36A—C36A—H36B109.5H36D—C36B—H36E109.5
C33A—C36A—H36C109.5C33B—C36B—H36F109.5
H36A—C36A—H36C109.5H36D—C36B—H36F109.5
H36B—C36A—H36C109.5H36E—C36B—H36F109.5
O2A—Mn1A—O1A—C1A−165.9 (2)O2B—Mn1B—O1B—C1B−179.6 (2)
N2A—Mn1A—O1A—C1A−75.6 (4)N2B—Mn1B—O1B—C1B−87.4 (3)
N1A—Mn1A—O1A—C1A−10.0 (2)N1B—Mn1B—O1B—C1B−17.7 (2)
Cl1A—Mn1A—O1A—C1A88.9 (2)Cl1B—Mn1B—O1B—C1B78.5 (2)
O1A—Mn1A—O2A—C20A−168.5 (2)O1B—Mn1B—O2B—C20B171.5 (2)
N2A—Mn1A—O2A—C20A28.8 (2)N2B—Mn1B—O2B—C20B14.3 (2)
N1A—Mn1A—O2A—C20A98.7 (3)N1B—Mn1B—O2B—C20B81.2 (4)
Cl1A—Mn1A—O2A—C20A−66.5 (2)Cl1B—Mn1B—O2B—C20B−81.8 (2)
O1A—Mn1A—N1A—C7A6.3 (2)O1B—Mn1B—N1B—C7B18.8 (2)
O2A—Mn1A—N1A—C7A99.0 (3)O2B—Mn1B—N1B—C7B109.0 (3)
N2A—Mn1A—N1A—C7A170.4 (2)N2B—Mn1B—N1B—C7B177.2 (2)
Cl1A—Mn1A—N1A—C7A−95.5 (2)Cl1B—Mn1B—N1B—C7B−87.7 (2)
O1A—Mn1A—N1A—C8A−174.62 (17)O1B—Mn1B—N1B—C8B−168.09 (19)
O2A—Mn1A—N1A—C8A−81.9 (3)O2B—Mn1B—N1B—C8B−77.9 (3)
N2A—Mn1A—N1A—C8A−10.50 (17)N2B—Mn1B—N1B—C8B−9.67 (18)
Cl1A—Mn1A—N1A—C8A83.59 (16)Cl1B—Mn1B—N1B—C8B85.42 (18)
O1A—Mn1A—N2A—C14A−110.8 (3)O1B—Mn1B—N2B—C14B−99.4 (3)
O2A—Mn1A—N2A—C14A−20.4 (2)O2B—Mn1B—N2B—C14B−7.5 (2)
N1A—Mn1A—N2A—C14A−177.6 (2)N1B—Mn1B—N2B—C14B−170.7 (2)
Cl1A—Mn1A—N2A—C14A84.4 (2)Cl1B—Mn1B—N2B—C14B94.2 (2)
O1A—Mn1A—N2A—C13A75.9 (3)O1B—Mn1B—N2B—C13B82.0 (3)
O2A—Mn1A—N2A—C13A166.31 (17)O2B—Mn1B—N2B—C13B173.94 (18)
N1A—Mn1A—N2A—C13A9.11 (17)N1B—Mn1B—N2B—C13B10.74 (18)
Cl1A—Mn1A—N2A—C13A−88.84 (16)Cl1B—Mn1B—N2B—C13B−84.38 (17)
Mn1A—O1A—C1A—C2A−172.34 (18)Mn1B—O1B—C1B—C6B8.4 (4)
Mn1A—O1A—C1A—C6A8.5 (4)Mn1B—O1B—C1B—C2B−174.36 (19)
O1A—C1A—C2A—C3A−177.7 (2)O1B—C1B—C2B—C3B179.0 (2)
C6A—C1A—C2A—C3A1.6 (4)C6B—C1B—C2B—C3B−3.7 (4)
O1A—C1A—C2A—C21A2.2 (4)O1B—C1B—C2B—C21B−2.4 (4)
C6A—C1A—C2A—C21A−178.5 (2)C6B—C1B—C2B—C21B174.9 (2)
C1A—C2A—C3A—C4A−0.1 (4)C1B—C2B—C3B—C4B2.4 (4)
C21A—C2A—C3A—C4A−180.0 (3)C21B—C2B—C3B—C4B−176.2 (3)
C2A—C3A—C4A—C5A−1.1 (4)C2B—C3B—C4B—C5B−0.4 (4)
C2A—C3A—C4A—C25A175.0 (3)C2B—C3B—C4B—C25B177.9 (3)
C3A—C4A—C5A—C6A0.8 (4)C3B—C4B—C5B—C6B−0.3 (4)
C25A—C4A—C5A—C6A−175.3 (2)C25B—C4B—C5B—C6B−178.5 (3)
C4A—C5A—C6A—C7A178.2 (2)O1B—C1B—C6B—C7B6.5 (4)
C4A—C5A—C6A—C1A0.7 (4)C2B—C1B—C6B—C7B−170.7 (3)
O1A—C1A—C6A—C5A177.3 (2)O1B—C1B—C6B—C5B−179.6 (2)
C2A—C1A—C6A—C5A−1.9 (4)C2B—C1B—C6B—C5B3.2 (4)
O1A—C1A—C6A—C7A−0.1 (4)C4B—C5B—C6B—C7B173.0 (3)
C2A—C1A—C6A—C7A−179.3 (2)C4B—C5B—C6B—C1B−1.2 (4)
C8A—N1A—C7A—C6A179.3 (2)C8B—N1B—C7B—C6B175.1 (3)
Mn1A—N1A—C7A—C6A−1.6 (4)Mn1B—N1B—C7B—C6B−12.3 (4)
C5A—C6A—C7A—N1A179.5 (2)C1B—C6B—C7B—N1B−3.6 (5)
C1A—C6A—C7A—N1A−3.0 (4)C5B—C6B—C7B—N1B−177.8 (3)
C7A—N1A—C8A—C13A−170.7 (2)C7B—N1B—C8B—C9B−0.3 (4)
Mn1A—N1A—C8A—C13A10.1 (3)Mn1B—N1B—C8B—C9B−173.7 (2)
C7A—N1A—C8A—C9A9.8 (4)C7B—N1B—C8B—C13B−179.9 (3)
Mn1A—N1A—C8A—C9A−169.4 (2)Mn1B—N1B—C8B—C13B6.8 (3)
C13A—C8A—C9A—C10A2.2 (4)C13B—C8B—C9B—C10B−2.0 (4)
N1A—C8A—C9A—C10A−178.3 (2)N1B—C8B—C9B—C10B178.5 (3)
C8A—C9A—C10A—C11A−0.6 (4)C8B—C9B—C10B—C11B−0.8 (4)
C9A—C10A—C11A—C12A−0.1 (4)C9B—C10B—C11B—C12B2.4 (4)
C10A—C11A—C12A—C13A−0.7 (4)C10B—C11B—C12B—C13B−1.0 (4)
C9A—C8A—C13A—C12A−3.0 (4)C11B—C12B—C13B—C8B−1.8 (4)
N1A—C8A—C13A—C12A177.5 (2)C11B—C12B—C13B—N2B179.0 (3)
C9A—C8A—C13A—N2A176.9 (2)C9B—C8B—C13B—C12B3.3 (4)
N1A—C8A—C13A—N2A−2.6 (3)N1B—C8B—C13B—C12B−177.1 (2)
C11A—C12A—C13A—C8A2.2 (4)C9B—C8B—C13B—N2B−177.4 (2)
C11A—C12A—C13A—N2A−177.7 (2)N1B—C8B—C13B—N2B2.2 (4)
C14A—N2A—C13A—C8A−179.5 (2)C14B—N2B—C13B—C12B−9.5 (4)
Mn1A—N2A—C13A—C8A−6.2 (3)Mn1B—N2B—C13B—C12B169.1 (2)
C14A—N2A—C13A—C12A0.4 (4)C14B—N2B—C13B—C8B171.2 (2)
Mn1A—N2A—C13A—C12A173.7 (2)Mn1B—N2B—C13B—C8B−10.1 (3)
C13A—N2A—C14A—C15A−179.0 (2)C13B—N2B—C14B—C15B−179.8 (3)
Mn1A—N2A—C14A—C15A8.4 (4)Mn1B—N2B—C14B—C15B1.7 (4)
N2A—C14A—C15A—C20A6.4 (4)N2B—C14B—C15B—C20B2.1 (4)
N2A—C14A—C15A—C16A−178.7 (3)N2B—C14B—C15B—C16B−179.5 (3)
C20A—C15A—C16A—C17A−0.9 (4)C20B—C15B—C16B—C17B−0.1 (4)
C14A—C15A—C16A—C17A−175.9 (2)C14B—C15B—C16B—C17B−178.6 (3)
C15A—C16A—C17A—C18A−1.4 (4)C15B—C16B—C17B—C18B−3.0 (4)
C15A—C16A—C17A—C33A175.9 (2)C15B—C16B—C17B—C33B174.1 (3)
C16A—C17A—C18A—C19A2.8 (4)C16B—C17B—C18B—C19B2.0 (4)
C33A—C17A—C18A—C19A−174.7 (3)C33B—C17B—C18B—C19B−175.3 (3)
C17A—C18A—C19A—C20A−1.6 (4)C17B—C18B—C19B—C20B2.2 (4)
C17A—C18A—C19A—C29A176.1 (3)C17B—C18B—C19B—C29B−179.0 (3)
Mn1A—O2A—C20A—C15A−23.0 (4)Mn1B—O2B—C20B—C15B−14.5 (4)
Mn1A—O2A—C20A—C19A160.04 (18)Mn1B—O2B—C20B—C19B166.7 (2)
C16A—C15A—C20A—O2A−174.8 (2)C16B—C15B—C20B—O2B−174.5 (2)
C14A—C15A—C20A—O2A−0.1 (4)C14B—C15B—C20B—O2B3.9 (4)
C16A—C15A—C20A—C19A2.2 (4)C16B—C15B—C20B—C19B4.3 (4)
C14A—C15A—C20A—C19A176.9 (2)C14B—C15B—C20B—C19B−177.3 (3)
C18A—C19A—C20A—O2A176.1 (2)C18B—C19B—C20B—O2B173.6 (2)
C29A—C19A—C20A—O2A−1.6 (4)C29B—C19B—C20B—O2B−5.2 (4)
C18A—C19A—C20A—C15A−0.9 (4)C18B—C19B—C20B—C15B−5.2 (4)
C29A—C19A—C20A—C15A−178.7 (2)C29B—C19B—C20B—C15B175.9 (3)
C3A—C2A—C21A—C22A−0.1 (4)C3B—C2B—C21B—C22B0.8 (4)
C1A—C2A—C21A—C22A−179.9 (3)C1B—C2B—C21B—C22B−177.7 (3)
C3A—C2A—C21A—C23A119.4 (3)C3B—C2B—C21B—C24B119.0 (3)
C1A—C2A—C21A—C23A−60.5 (3)C1B—C2B—C21B—C24B−59.5 (3)
C3A—C2A—C21A—C24A−119.0 (3)C3B—C2B—C21B—C23B−119.5 (3)
C1A—C2A—C21A—C24A61.1 (3)C1B—C2B—C21B—C23B62.0 (3)
C5A—C4A—C25A—C26A92.4 (3)C5B—C4B—C25B—C26B−117.2 (3)
C3A—C4A—C25A—C26A−83.5 (3)C3B—C4B—C25B—C26B64.6 (3)
C5A—C4A—C25A—C27A−27.6 (4)C5B—C4B—C25B—C28B2.7 (4)
C3A—C4A—C25A—C27A156.5 (3)C3B—C4B—C25B—C28B−175.4 (2)
C5A—C4A—C25A—C28A−147.4 (3)C5B—C4B—C25B—C27B123.3 (3)
C3A—C4A—C25A—C28A36.6 (3)C3B—C4B—C25B—C27B−54.8 (3)
C18A—C19A—C29A—C32A−110.7 (3)C18B—C19B—C29B—C32B125.7 (3)
C20A—C19A—C29A—C32A67.0 (3)C20B—C19B—C29B—C32B−55.5 (3)
C18A—C19A—C29A—C30A8.9 (4)C18B—C19B—C29B—C30B6.8 (4)
C20A—C19A—C29A—C30A−173.4 (2)C20B—C19B—C29B—C30B−174.4 (3)
C18A—C19A—C29A—C31A128.7 (3)C18B—C19B—C29B—C31B−112.9 (3)
C20A—C19A—C29A—C31A−53.7 (3)C20B—C19B—C29B—C31B65.9 (3)
C16A—C17A—C33A—C35A0.4 (4)C16B—C17B—C33B—C34B−97.1 (3)
C18A—C17A—C33A—C35A177.6 (2)C18B—C17B—C33B—C34B79.9 (3)
C16A—C17A—C33A—C36A−119.5 (3)C16B—C17B—C33B—C35B24.3 (4)
C18A—C17A—C33A—C36A57.8 (3)C18B—C17B—C33B—C35B−158.6 (3)
C16A—C17A—C33A—C34A121.2 (3)C16B—C17B—C33B—C36B143.9 (3)
C18A—C17A—C33A—C34A−61.6 (3)C18B—C17B—C33B—C36B−39.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7A—H7A···Cl1Ai0.932.813.648 (3)151
C23A—H23A···O1A0.962.322.963 (4)124
C24A—H24A···O1A0.962.383.021 (4)124
C31A—H31B···O2A0.962.252.914 (3)125
C32A—H32C···O2A0.962.463.079 (4)122
C14B—H14B···Cl1Bii0.932.793.624 (3)150
C23B—H23E···O1B0.962.352.994 (4)124
C24B—H24F···O1B0.962.332.982 (4)125
C31B—H31D···O2B0.962.403.035 (4)124
C32B—H32F···O2B0.962.292.957 (4)126
C28A—H28B···Cg1iii0.962.703.658 (4)174
C36B—H36D···Cg2iv0.962.643.597 (4)174

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2582).

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