metal-organic compounds
The cocrystal aquachlorido{6,6′-di-tert-butyl-2,2′-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato-κ4O,N,N′,O′}manganese(III)–chlorido{6,6′-di-tert-butyl-2,2′-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato-κ4O,N,N′,O′}(methanol-κO)manganese(III) (1/1)
aSchool of Chemical Science, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
The 28H30N2O2)Cl(H2O)][Mn(C28H30N2O2)Cl(CH3OH)], contains two discrete MnIII complexes of a Schiff base ligand, with an N2O2 donor set. Both MnIII centers are in a distorted octahedral geometry with the N2O2 donor atoms of the tetradentate Schiff base dianion in the equatorial plane. The axial positions in the coordination environment of one MnIII complex are occupied by a chloride ion and a water molecule, but a methanol molecule replaces the water molecule in the other complex. The coordinated water molecule takes part in an O—H⋯Cl hydrogen bond between the two MnIII complexes. In the O—H⋯Cl hydrogen bonds link the molecules into infinite one-dimensional chains along the [100] direction. The is stabilized by O—H⋯Cl hydrogen bonds together with weak C—H⋯O and C—H⋯Cl interactions. A C—H⋯π interaction is also observed in the crystal structure.
of the title complex, [Mn(CRelated literature
For bond-length data, see: Allen et al. (1987). For related structures, see for example: Eltayeb et al. (2007, 2008); Habibi et al. (2007); Mitra et al. (2006). For background to applications of manganese complexes, see for example: Dixit & Srinivasan (1988); Glatzel et al. (2004); Lu et al. (2006); Stallings et al. (1985).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
Supporting information
10.1107/S1600536808006818/sj2472sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808006818/sj2472Isup2.hkl
The title compound was synthesized by adding 3-tert-butyl-2-hydroxybenzaldehyde (0.72 ml, 4 mmol) to a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (30 ml). The mixture was refluxed with stirring for half an hour. Manganese chloride tetrahydrate (0.394 g, 2 mmol) in ethanol (10 ml) was then added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was refluxed at room temperature for three hours. A brown precipitate was obtained, washed with about 5 ml e thanol, dried, and then washed with copious quantities of diethylether. Brown single crystals of the title compound suitable for x-ray
were recrystallized from methanol/acetone (2:1 v/v) by slow evaporation of the solvent at room temperature after three weeks.All H atoms were placed in calculated positions with d(O—H) = 0.85 Å, Uiso=1.2Ueq, d(C—H) = 0.93 Å, Uiso=1.2Ueq(C) for CH and aromatic, 0.96 Å, Uiso = 1.5Ueq(C) for CH3 atoms. A rotating group model was used for the methyl groups. The highest residual electron density peak is located at 1.00 Å from Mn1B and the deepest hole is located at 0.85 Å from Mn1A.
Data collection: APEX2 (Bruker, 2005); cell
APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering. H atoms of the Schiff base ligand were omitted for clarify. The O—H···Cl hydrogen bond is drawn as a dashed line. | |
Fig. 2. The crystal packing of (I), viewed along the c axis showing the chains running along the [1 0 0] direction. Hydrogen bonds are drawn as dashed lines. |
[Mn(C28H30N2O2)Cl(H2O)][Mn(C28H30N2O2)Cl(CH4O)] | Z = 2 |
Mr = 1083.92 | F(000) = 1136 |
Triclinic, P1 | Dx = 1.390 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1080 (3) Å | Cell parameters from 10108 reflections |
b = 13.8794 (3) Å | θ = 1.6–26.0° |
c = 14.6085 (3) Å | µ = 0.65 mm−1 |
α = 95.177 (1)° | T = 100 K |
β = 99.996 (1)° | Plate, brown |
γ = 95.639 (1)° | 0.38 × 0.33 × 0.03 mm |
V = 2589.08 (10) Å3 |
Bruker SMART APEX2 CCD area-detector diffractometer | 10108 independent reflections |
Radiation source: fine-focus sealed tube | 6163 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.076 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 1.6° |
ω scans | h = −16→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −17→17 |
Tmin = 0.791, Tmax = 0.981 | l = −18→18 |
37620 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.069P)2 + 0.4229P] where P = (Fo2 + 2Fc2)/3 |
10108 reflections | (Δ/σ)max < 0.001 |
653 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
[Mn(C28H30N2O2)Cl(H2O)][Mn(C28H30N2O2)Cl(CH4O)] | γ = 95.639 (1)° |
Mr = 1083.92 | V = 2589.08 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.1080 (3) Å | Mo Kα radiation |
b = 13.8794 (3) Å | µ = 0.65 mm−1 |
c = 14.6085 (3) Å | T = 100 K |
α = 95.177 (1)° | 0.38 × 0.33 × 0.03 mm |
β = 99.996 (1)° |
Bruker SMART APEX2 CCD area-detector diffractometer | 10108 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 6163 reflections with I > 2σ(I) |
Tmin = 0.791, Tmax = 0.981 | Rint = 0.076 |
37620 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.57 e Å−3 |
10108 reflections | Δρmin = −0.52 e Å−3 |
653 parameters |
Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment |
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. |
x | y | z | Uiso*/Ueq | ||
Mn1A | 0.34120 (5) | 0.29619 (4) | 0.11581 (4) | 0.01967 (16) | |
Cl1A | 0.14711 (8) | 0.25826 (7) | 0.05064 (6) | 0.0277 (2) | |
O1A | 0.3338 (2) | 0.41678 (17) | 0.18009 (16) | 0.0239 (6) | |
O2A | 0.3473 (2) | 0.23461 (17) | 0.22530 (16) | 0.0221 (6) | |
O1WA | 0.5284 (2) | 0.32040 (19) | 0.15261 (17) | 0.0298 (7) | |
H1WA | 0.5748 | 0.3629 | 0.1852 | 0.045* | |
H2WA | 0.5569 | 0.2691 | 0.1424 | 0.045* | |
N1A | 0.3597 (2) | 0.3558 (2) | 0.0007 (2) | 0.0202 (7) | |
N2A | 0.3661 (2) | 0.1774 (2) | 0.0413 (2) | 0.0205 (7) | |
C1A | 0.3384 (3) | 0.5060 (3) | 0.1543 (2) | 0.0201 (8) | |
C2A | 0.3191 (3) | 0.5846 (3) | 0.2162 (3) | 0.0229 (9) | |
C3A | 0.3332 (3) | 0.6771 (3) | 0.1890 (3) | 0.0255 (9) | |
H3AA | 0.3241 | 0.7295 | 0.2300 | 0.031* | |
C4A | 0.3601 (3) | 0.6964 (3) | 0.1044 (3) | 0.0262 (9) | |
H4AA | 0.3688 | 0.7601 | 0.0896 | 0.031* | |
C5A | 0.3735 (3) | 0.6213 (3) | 0.0433 (3) | 0.0235 (9) | |
H5AA | 0.3901 | 0.6336 | −0.0142 | 0.028* | |
C6A | 0.3624 (3) | 0.5244 (2) | 0.0661 (2) | 0.0194 (8) | |
C7A | 0.3706 (3) | 0.4493 (3) | −0.0049 (2) | 0.0211 (8) | |
H7AA | 0.3851 | 0.4691 | −0.0609 | 0.025* | |
C8A | 0.3653 (3) | 0.2870 (3) | −0.0760 (2) | 0.0206 (8) | |
C9A | 0.3658 (3) | 0.3080 (3) | −0.1665 (3) | 0.0263 (9) | |
H9AA | 0.3611 | 0.3713 | −0.1816 | 0.032* | |
C10A | 0.3733 (3) | 0.2344 (3) | −0.2347 (3) | 0.0288 (10) | |
H10A | 0.3737 | 0.2483 | −0.2957 | 0.035* | |
C11A | 0.3802 (3) | 0.1400 (3) | −0.2124 (3) | 0.0287 (10) | |
H11A | 0.3860 | 0.0912 | −0.2585 | 0.034* | |
C12A | 0.3787 (3) | 0.1177 (3) | −0.1231 (3) | 0.0248 (9) | |
H12A | 0.3830 | 0.0541 | −0.1090 | 0.030* | |
C13A | 0.3707 (3) | 0.1906 (3) | −0.0536 (3) | 0.0220 (9) | |
C14A | 0.3772 (3) | 0.0939 (3) | 0.0743 (3) | 0.0231 (9) | |
H14A | 0.3829 | 0.0415 | 0.0317 | 0.028* | |
C15A | 0.3814 (3) | 0.0753 (3) | 0.1691 (3) | 0.0224 (9) | |
C16A | 0.3978 (3) | −0.0201 (3) | 0.1902 (3) | 0.0253 (9) | |
H16A | 0.4005 | −0.0681 | 0.1423 | 0.030* | |
C17A | 0.4095 (3) | −0.0422 (3) | 0.2800 (3) | 0.0272 (9) | |
H17A | 0.4169 | −0.1057 | 0.2933 | 0.033* | |
C18A | 0.4104 (3) | 0.0318 (3) | 0.3524 (3) | 0.0245 (9) | |
H18A | 0.4216 | 0.0161 | 0.4137 | 0.029* | |
C19A | 0.3957 (3) | 0.1268 (3) | 0.3376 (3) | 0.0217 (9) | |
C20A | 0.3739 (3) | 0.1474 (3) | 0.2431 (3) | 0.0218 (9) | |
C21A | 0.2845 (4) | 0.5662 (3) | 0.3085 (3) | 0.0331 (11) | |
C22A | 0.2646 (4) | 0.6604 (3) | 0.3618 (3) | 0.0457 (13) | |
H22A | 0.2109 | 0.6893 | 0.3241 | 0.069* | |
H22B | 0.3275 | 0.7048 | 0.3756 | 0.069* | |
H22C | 0.2429 | 0.6461 | 0.4190 | 0.069* | |
C23A | 0.1827 (4) | 0.4977 (3) | 0.2886 (3) | 0.0502 (14) | |
H23A | 0.1294 | 0.5274 | 0.2512 | 0.075* | |
H23B | 0.1617 | 0.4851 | 0.3466 | 0.075* | |
H23C | 0.1930 | 0.4375 | 0.2556 | 0.075* | |
C24A | 0.3691 (4) | 0.5217 (3) | 0.3717 (3) | 0.0461 (13) | |
H24A | 0.3477 | 0.5127 | 0.4303 | 0.069* | |
H24B | 0.4331 | 0.5645 | 0.3826 | 0.069* | |
H24C | 0.3795 | 0.4598 | 0.3419 | 0.069* | |
C25A | 0.4097 (3) | 0.2082 (3) | 0.4191 (3) | 0.0285 (10) | |
C26A | 0.3079 (3) | 0.2515 (3) | 0.4249 (3) | 0.0389 (11) | |
H26A | 0.2885 | 0.2850 | 0.3709 | 0.058* | |
H26B | 0.3174 | 0.2965 | 0.4804 | 0.058* | |
H26C | 0.2539 | 0.2002 | 0.4270 | 0.058* | |
C27A | 0.4468 (4) | 0.1702 (3) | 0.5141 (3) | 0.0396 (12) | |
H27A | 0.5095 | 0.1404 | 0.5121 | 0.059* | |
H27B | 0.3936 | 0.1231 | 0.5264 | 0.059* | |
H27C | 0.4603 | 0.2236 | 0.5628 | 0.059* | |
C28A | 0.4928 (3) | 0.2884 (3) | 0.4073 (3) | 0.0309 (10) | |
H28A | 0.4711 | 0.3157 | 0.3500 | 0.046* | |
H28B | 0.5573 | 0.2617 | 0.4057 | 0.046* | |
H28C | 0.5022 | 0.3385 | 0.4589 | 0.046* | |
Mn1B | 0.83334 (4) | 0.18866 (4) | 0.15141 (4) | 0.01899 (16) | |
Cl1B | 0.64003 (7) | 0.14689 (6) | 0.08462 (6) | 0.0245 (2) | |
O1B | 0.8253 (2) | 0.31322 (17) | 0.21049 (16) | 0.0249 (6) | |
O2B | 0.83043 (19) | 0.12841 (17) | 0.26015 (16) | 0.0214 (6) | |
O3B | 1.0116 (2) | 0.2132 (2) | 0.19280 (19) | 0.0402 (8) | |
H1O3 | 1.0449 | 0.2199 | 0.1368 | 0.060* | |
N1B | 0.8598 (2) | 0.2431 (2) | 0.03600 (19) | 0.0209 (7) | |
N2B | 0.8582 (2) | 0.0659 (2) | 0.0806 (2) | 0.0197 (7) | |
C1B | 0.8462 (3) | 0.4012 (3) | 0.1851 (3) | 0.0222 (9) | |
C2B | 0.8448 (3) | 0.4853 (3) | 0.2486 (2) | 0.0217 (9) | |
C3B | 0.8641 (3) | 0.5759 (3) | 0.2182 (3) | 0.0279 (10) | |
H3BA | 0.8629 | 0.6309 | 0.2591 | 0.034* | |
C4B | 0.8853 (3) | 0.5891 (3) | 0.1302 (3) | 0.0297 (10) | |
H4BA | 0.8967 | 0.6514 | 0.1126 | 0.036* | |
C5B | 0.8889 (3) | 0.5093 (3) | 0.0698 (3) | 0.0270 (9) | |
H5BA | 0.9038 | 0.5171 | 0.0108 | 0.032* | |
C6B | 0.8703 (3) | 0.4152 (3) | 0.0963 (3) | 0.0248 (9) | |
C7B | 0.8741 (3) | 0.3358 (3) | 0.0270 (3) | 0.0228 (9) | |
H7BA | 0.8884 | 0.3523 | −0.0301 | 0.027* | |
C8B | 0.8655 (3) | 0.1710 (3) | −0.0386 (2) | 0.0218 (9) | |
C9B | 0.8699 (3) | 0.1896 (3) | −0.1297 (2) | 0.0249 (9) | |
H9BA | 0.8695 | 0.2527 | −0.1462 | 0.030* | |
C10B | 0.8751 (3) | 0.1127 (3) | −0.1958 (3) | 0.0277 (9) | |
H10B | 0.8784 | 0.1244 | −0.2570 | 0.033* | |
C11B | 0.8753 (3) | 0.0185 (3) | −0.1711 (3) | 0.0269 (9) | |
H11B | 0.8788 | −0.0326 | −0.2158 | 0.032* | |
C12B | 0.8703 (3) | 0.0002 (3) | −0.0815 (3) | 0.0260 (9) | |
H12B | 0.8705 | −0.0632 | −0.0656 | 0.031* | |
C13B | 0.8650 (3) | 0.0761 (3) | −0.0138 (2) | 0.0215 (8) | |
C14B | 0.8714 (3) | −0.0154 (3) | 0.1169 (3) | 0.0234 (9) | |
H14B | 0.8847 | −0.0674 | 0.0777 | 0.028* | |
C15B | 0.8675 (3) | −0.0319 (3) | 0.2107 (2) | 0.0203 (8) | |
C16B | 0.8852 (3) | −0.1259 (3) | 0.2357 (3) | 0.0254 (9) | |
H16B | 0.8978 | −0.1728 | 0.1906 | 0.030* | |
C17B | 0.8843 (3) | −0.1491 (3) | 0.3238 (3) | 0.0284 (10) | |
H17B | 0.8978 | −0.2107 | 0.3394 | 0.034* | |
C18B | 0.8628 (3) | −0.0794 (3) | 0.3906 (3) | 0.0255 (9) | |
H18B | 0.8616 | −0.0964 | 0.4506 | 0.031* | |
C19B | 0.8432 (3) | 0.0140 (3) | 0.3720 (2) | 0.0204 (8) | |
C20B | 0.8468 (3) | 0.0393 (3) | 0.2798 (2) | 0.0194 (8) | |
C21B | 0.8251 (3) | 0.4751 (3) | 0.3487 (3) | 0.0272 (9) | |
C22B | 0.8269 (4) | 0.5748 (3) | 0.4038 (3) | 0.0345 (11) | |
H22D | 0.8943 | 0.6111 | 0.4094 | 0.052* | |
H22E | 0.8128 | 0.5659 | 0.4651 | 0.052* | |
H22F | 0.7746 | 0.6099 | 0.3716 | 0.052* | |
C23B | 0.7180 (3) | 0.4184 (3) | 0.3464 (3) | 0.0389 (11) | |
H23D | 0.7068 | 0.4140 | 0.4092 | 0.058* | |
H23E | 0.7155 | 0.3540 | 0.3153 | 0.058* | |
H23F | 0.6645 | 0.4515 | 0.3134 | 0.058* | |
C24B | 0.9116 (4) | 0.4233 (3) | 0.3996 (3) | 0.0334 (10) | |
H24D | 0.9777 | 0.4613 | 0.4031 | 0.050* | |
H24E | 0.9118 | 0.3605 | 0.3663 | 0.050* | |
H24F | 0.8997 | 0.4154 | 0.4617 | 0.050* | |
C25B | 0.8180 (3) | 0.0874 (3) | 0.4473 (2) | 0.0252 (9) | |
C26B | 0.7086 (3) | 0.1171 (3) | 0.4154 (3) | 0.0377 (11) | |
H26D | 0.6577 | 0.0610 | 0.4087 | 0.057* | |
H26E | 0.7055 | 0.1432 | 0.3565 | 0.057* | |
H26F | 0.6943 | 0.1655 | 0.4612 | 0.057* | |
C27B | 0.8188 (3) | 0.0454 (3) | 0.5401 (3) | 0.0343 (10) | |
H27D | 0.8874 | 0.0294 | 0.5635 | 0.051* | |
H27E | 0.7699 | −0.0124 | 0.5310 | 0.051* | |
H27F | 0.7996 | 0.0926 | 0.5843 | 0.051* | |
C28B | 0.9001 (4) | 0.1775 (3) | 0.4649 (3) | 0.0349 (11) | |
H28D | 0.9684 | 0.1576 | 0.4815 | 0.052* | |
H28E | 0.8868 | 0.2213 | 0.5151 | 0.052* | |
H28F | 0.8964 | 0.2099 | 0.4093 | 0.052* | |
C29B | 1.0736 (4) | 0.2242 (4) | 0.2779 (4) | 0.0556 (14) | |
H29D | 1.1444 | 0.2187 | 0.2709 | 0.083* | |
H29E | 1.0512 | 0.1745 | 0.3141 | 0.083* | |
H29F | 1.0694 | 0.2871 | 0.3093 | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1A | 0.0292 (4) | 0.0130 (3) | 0.0194 (3) | 0.0058 (2) | 0.0105 (3) | 0.0002 (2) |
Cl1A | 0.0274 (6) | 0.0307 (5) | 0.0277 (5) | 0.0065 (4) | 0.0099 (4) | 0.0058 (4) |
O1A | 0.0405 (17) | 0.0142 (13) | 0.0208 (14) | 0.0083 (12) | 0.0123 (12) | 0.0027 (10) |
O2A | 0.0324 (16) | 0.0143 (13) | 0.0245 (14) | 0.0098 (11) | 0.0134 (12) | 0.0053 (10) |
O1WA | 0.0301 (17) | 0.0258 (15) | 0.0343 (16) | 0.0080 (13) | 0.0078 (13) | −0.0012 (12) |
N1A | 0.0219 (18) | 0.0177 (16) | 0.0211 (17) | 0.0047 (14) | 0.0058 (14) | −0.0031 (13) |
N2A | 0.0212 (18) | 0.0168 (16) | 0.0235 (18) | 0.0052 (14) | 0.0042 (14) | −0.0009 (13) |
C1A | 0.025 (2) | 0.0156 (19) | 0.020 (2) | 0.0034 (17) | 0.0042 (17) | 0.0052 (15) |
C2A | 0.030 (2) | 0.0141 (19) | 0.025 (2) | 0.0035 (17) | 0.0058 (18) | 0.0002 (15) |
C3A | 0.030 (2) | 0.0161 (19) | 0.030 (2) | 0.0054 (17) | 0.0018 (18) | 0.0000 (16) |
C4A | 0.026 (2) | 0.018 (2) | 0.033 (2) | 0.0007 (17) | 0.0018 (19) | 0.0044 (17) |
C5A | 0.024 (2) | 0.021 (2) | 0.025 (2) | −0.0020 (17) | 0.0033 (17) | 0.0070 (16) |
C6A | 0.021 (2) | 0.0137 (18) | 0.024 (2) | 0.0017 (16) | 0.0062 (17) | 0.0022 (15) |
C7A | 0.020 (2) | 0.024 (2) | 0.021 (2) | 0.0033 (17) | 0.0069 (17) | 0.0048 (16) |
C8A | 0.021 (2) | 0.024 (2) | 0.017 (2) | 0.0049 (17) | 0.0055 (16) | −0.0023 (15) |
C9A | 0.028 (2) | 0.025 (2) | 0.026 (2) | 0.0044 (18) | 0.0079 (18) | −0.0030 (17) |
C10A | 0.031 (3) | 0.039 (2) | 0.017 (2) | 0.006 (2) | 0.0059 (18) | −0.0020 (17) |
C11A | 0.021 (2) | 0.034 (2) | 0.030 (2) | 0.0060 (19) | 0.0063 (18) | −0.0088 (18) |
C12A | 0.025 (2) | 0.025 (2) | 0.025 (2) | 0.0049 (18) | 0.0060 (18) | −0.0009 (17) |
C13A | 0.016 (2) | 0.023 (2) | 0.028 (2) | 0.0049 (17) | 0.0080 (17) | −0.0031 (16) |
C14A | 0.022 (2) | 0.018 (2) | 0.028 (2) | 0.0051 (17) | 0.0056 (18) | −0.0066 (16) |
C15A | 0.020 (2) | 0.0170 (19) | 0.031 (2) | 0.0039 (16) | 0.0075 (18) | −0.0004 (16) |
C16A | 0.028 (2) | 0.0150 (19) | 0.032 (2) | 0.0043 (17) | 0.0058 (18) | −0.0043 (16) |
C17A | 0.034 (3) | 0.0130 (19) | 0.038 (3) | 0.0083 (18) | 0.011 (2) | 0.0081 (17) |
C18A | 0.028 (2) | 0.022 (2) | 0.029 (2) | 0.0087 (18) | 0.0106 (18) | 0.0116 (17) |
C19A | 0.024 (2) | 0.020 (2) | 0.025 (2) | 0.0066 (17) | 0.0110 (17) | 0.0059 (16) |
C20A | 0.022 (2) | 0.0182 (19) | 0.028 (2) | 0.0060 (17) | 0.0104 (17) | 0.0057 (16) |
C21A | 0.059 (3) | 0.020 (2) | 0.025 (2) | 0.016 (2) | 0.017 (2) | −0.0006 (17) |
C22A | 0.081 (4) | 0.029 (2) | 0.033 (3) | 0.021 (2) | 0.022 (2) | 0.0010 (19) |
C23A | 0.075 (4) | 0.036 (3) | 0.054 (3) | 0.012 (3) | 0.046 (3) | 0.005 (2) |
C24A | 0.090 (4) | 0.031 (2) | 0.020 (2) | 0.028 (3) | 0.007 (2) | 0.0015 (18) |
C25A | 0.043 (3) | 0.025 (2) | 0.023 (2) | 0.0136 (19) | 0.0112 (19) | 0.0062 (17) |
C26A | 0.053 (3) | 0.034 (2) | 0.040 (3) | 0.019 (2) | 0.029 (2) | 0.010 (2) |
C27A | 0.071 (4) | 0.030 (2) | 0.026 (2) | 0.020 (2) | 0.020 (2) | 0.0065 (18) |
C28A | 0.049 (3) | 0.022 (2) | 0.023 (2) | 0.011 (2) | 0.006 (2) | 0.0033 (17) |
Mn1B | 0.0254 (4) | 0.0158 (3) | 0.0171 (3) | 0.0053 (2) | 0.0075 (3) | −0.0013 (2) |
Cl1B | 0.0258 (6) | 0.0210 (5) | 0.0282 (5) | 0.0066 (4) | 0.0074 (4) | 0.0021 (4) |
O1B | 0.0373 (17) | 0.0171 (14) | 0.0210 (14) | −0.0019 (12) | 0.0118 (12) | −0.0012 (11) |
O2B | 0.0307 (16) | 0.0181 (13) | 0.0176 (13) | 0.0090 (12) | 0.0082 (11) | 0.0005 (10) |
O3B | 0.0304 (18) | 0.069 (2) | 0.0187 (16) | −0.0024 (16) | 0.0036 (13) | 0.0001 (14) |
N1B | 0.0265 (19) | 0.0211 (17) | 0.0161 (16) | 0.0058 (14) | 0.0076 (14) | −0.0028 (13) |
N2B | 0.0194 (18) | 0.0207 (17) | 0.0191 (17) | 0.0041 (14) | 0.0047 (14) | −0.0015 (13) |
C1B | 0.023 (2) | 0.019 (2) | 0.024 (2) | 0.0010 (17) | 0.0046 (17) | −0.0014 (16) |
C2B | 0.027 (2) | 0.0153 (19) | 0.024 (2) | 0.0025 (16) | 0.0088 (17) | −0.0012 (15) |
C3B | 0.037 (3) | 0.021 (2) | 0.024 (2) | 0.0052 (19) | 0.0039 (19) | −0.0040 (17) |
C4B | 0.040 (3) | 0.016 (2) | 0.034 (2) | 0.0042 (19) | 0.007 (2) | 0.0080 (17) |
C5B | 0.034 (3) | 0.026 (2) | 0.021 (2) | 0.0020 (19) | 0.0048 (18) | 0.0023 (17) |
C6B | 0.027 (2) | 0.025 (2) | 0.020 (2) | −0.0010 (18) | 0.0014 (18) | −0.0003 (16) |
C7B | 0.023 (2) | 0.026 (2) | 0.019 (2) | 0.0024 (18) | 0.0062 (17) | 0.0028 (16) |
C8B | 0.021 (2) | 0.028 (2) | 0.018 (2) | 0.0062 (17) | 0.0077 (17) | −0.0015 (16) |
C9B | 0.027 (2) | 0.029 (2) | 0.020 (2) | 0.0083 (18) | 0.0069 (18) | 0.0028 (16) |
C10B | 0.025 (2) | 0.041 (3) | 0.018 (2) | 0.0084 (19) | 0.0049 (18) | −0.0017 (17) |
C11B | 0.025 (2) | 0.033 (2) | 0.021 (2) | 0.0058 (18) | 0.0051 (18) | −0.0099 (17) |
C12B | 0.026 (2) | 0.024 (2) | 0.028 (2) | 0.0072 (18) | 0.0059 (18) | −0.0048 (17) |
C13B | 0.018 (2) | 0.028 (2) | 0.018 (2) | 0.0026 (17) | 0.0064 (16) | −0.0013 (16) |
C14B | 0.021 (2) | 0.018 (2) | 0.031 (2) | 0.0064 (17) | 0.0071 (18) | −0.0023 (16) |
C15B | 0.019 (2) | 0.0178 (19) | 0.025 (2) | 0.0032 (16) | 0.0065 (17) | −0.0003 (16) |
C16B | 0.026 (2) | 0.017 (2) | 0.033 (2) | 0.0041 (17) | 0.0067 (18) | −0.0017 (17) |
C17B | 0.030 (3) | 0.018 (2) | 0.038 (3) | 0.0049 (18) | 0.007 (2) | 0.0050 (18) |
C18B | 0.027 (2) | 0.024 (2) | 0.027 (2) | 0.0041 (18) | 0.0073 (18) | 0.0035 (17) |
C19B | 0.022 (2) | 0.022 (2) | 0.017 (2) | 0.0048 (17) | 0.0032 (16) | 0.0009 (15) |
C20B | 0.018 (2) | 0.0187 (19) | 0.022 (2) | 0.0065 (16) | 0.0043 (16) | 0.0003 (15) |
C21B | 0.040 (3) | 0.018 (2) | 0.023 (2) | 0.0020 (18) | 0.0077 (19) | −0.0047 (16) |
C22B | 0.054 (3) | 0.023 (2) | 0.027 (2) | 0.004 (2) | 0.014 (2) | −0.0037 (17) |
C23B | 0.045 (3) | 0.037 (3) | 0.036 (3) | −0.001 (2) | 0.021 (2) | −0.008 (2) |
C24B | 0.052 (3) | 0.025 (2) | 0.023 (2) | 0.006 (2) | 0.007 (2) | −0.0022 (17) |
C25B | 0.033 (3) | 0.027 (2) | 0.018 (2) | 0.0117 (18) | 0.0055 (18) | 0.0000 (16) |
C26B | 0.045 (3) | 0.047 (3) | 0.028 (2) | 0.028 (2) | 0.012 (2) | 0.003 (2) |
C27B | 0.047 (3) | 0.035 (2) | 0.024 (2) | 0.012 (2) | 0.010 (2) | 0.0031 (18) |
C28B | 0.058 (3) | 0.022 (2) | 0.023 (2) | 0.010 (2) | 0.001 (2) | −0.0042 (17) |
C29B | 0.049 (3) | 0.057 (3) | 0.063 (4) | 0.003 (3) | 0.021 (3) | −0.002 (3) |
Mn1A—O1A | 1.863 (2) | Mn1B—N1B | 1.978 (3) |
Mn1A—O2A | 1.874 (2) | Mn1B—N2B | 1.997 (3) |
Mn1A—N2A | 1.979 (3) | Mn1B—O3B | 2.293 (3) |
Mn1A—N1A | 1.981 (3) | Mn1B—Cl1B | 2.5416 (11) |
Mn1A—O1WA | 2.402 (3) | O1B—C1B | 1.325 (4) |
Mn1A—Cl1A | 2.5420 (12) | O2B—C20B | 1.325 (4) |
O1A—C1A | 1.325 (4) | O3B—C29B | 1.349 (5) |
O2A—C20A | 1.327 (4) | O3B—H1O3 | 0.9992 |
O1WA—H1WA | 0.8500 | N1B—C7B | 1.305 (5) |
O1WA—H2WA | 0.8500 | N1B—C8B | 1.429 (4) |
N1A—C7A | 1.303 (4) | N2B—C14B | 1.303 (4) |
N1A—C8A | 1.421 (4) | N2B—C13B | 1.416 (4) |
N2A—C14A | 1.306 (4) | C1B—C6B | 1.412 (5) |
N2A—C13A | 1.425 (5) | C1B—C2B | 1.429 (5) |
C1A—C6A | 1.418 (5) | C2B—C3B | 1.385 (5) |
C1A—C2A | 1.423 (5) | C2B—C21B | 1.544 (5) |
C2A—C3A | 1.383 (5) | C3B—C4B | 1.385 (5) |
C2A—C21A | 1.531 (5) | C3B—H3BA | 0.9300 |
C3A—C4A | 1.384 (5) | C4B—C5B | 1.361 (5) |
C3A—H3AA | 0.9300 | C4B—H4BA | 0.9300 |
C4A—C5A | 1.355 (5) | C5B—C6B | 1.406 (5) |
C4A—H4AA | 0.9300 | C5B—H5BA | 0.9300 |
C5A—C6A | 1.414 (5) | C6B—C7B | 1.439 (5) |
C5A—H5AA | 0.9300 | C7B—H7BA | 0.9300 |
C6A—C7A | 1.429 (5) | C8B—C9B | 1.388 (5) |
C7A—H7AA | 0.9300 | C8B—C13B | 1.398 (5) |
C8A—C9A | 1.380 (5) | C9B—C10B | 1.388 (5) |
C8A—C13A | 1.412 (5) | C9B—H9BA | 0.9300 |
C9A—C10A | 1.384 (5) | C10B—C11B | 1.389 (5) |
C9A—H9AA | 0.9300 | C10B—H10B | 0.9300 |
C10A—C11A | 1.385 (6) | C11B—C12B | 1.367 (5) |
C10A—H10A | 0.9300 | C11B—H11B | 0.9300 |
C11A—C12A | 1.370 (5) | C12B—C13B | 1.394 (5) |
C11A—H11A | 0.9300 | C12B—H12B | 0.9300 |
C12A—C13A | 1.391 (5) | C14B—C15B | 1.418 (5) |
C12A—H12A | 0.9300 | C14B—H14B | 0.9300 |
C14A—C15A | 1.426 (5) | C15B—C16B | 1.416 (5) |
C14A—H14A | 0.9300 | C15B—C20B | 1.427 (5) |
C15A—C16A | 1.414 (5) | C16B—C17B | 1.356 (5) |
C15A—C20A | 1.428 (5) | C16B—H16B | 0.9300 |
C16A—C17A | 1.361 (5) | C17B—C18B | 1.395 (5) |
C16A—H16A | 0.9300 | C17B—H17B | 0.9300 |
C17A—C18A | 1.405 (5) | C18B—C19B | 1.387 (5) |
C17A—H17A | 0.9300 | C18B—H18B | 0.9300 |
C18A—C19A | 1.382 (5) | C19B—C20B | 1.430 (5) |
C18A—H18A | 0.9300 | C19B—C25B | 1.531 (5) |
C19A—C20A | 1.421 (5) | C21B—C24B | 1.524 (6) |
C19A—C25A | 1.540 (5) | C21B—C22B | 1.533 (5) |
C21A—C23A | 1.528 (6) | C21B—C23B | 1.535 (6) |
C21A—C22A | 1.528 (5) | C22B—H22D | 0.9600 |
C21A—C24A | 1.532 (6) | C22B—H22E | 0.9600 |
C22A—H22A | 0.9600 | C22B—H22F | 0.9600 |
C22A—H22B | 0.9600 | C23B—H23D | 0.9600 |
C22A—H22C | 0.9600 | C23B—H23E | 0.9600 |
C23A—H23A | 0.9600 | C23B—H23F | 0.9600 |
C23A—H23B | 0.9600 | C24B—H24D | 0.9600 |
C23A—H23C | 0.9600 | C24B—H24E | 0.9600 |
C24A—H24A | 0.9600 | C24B—H24F | 0.9600 |
C24A—H24B | 0.9600 | C25B—C27B | 1.522 (5) |
C24A—H24C | 0.9600 | C25B—C26B | 1.537 (5) |
C25A—C28A | 1.522 (5) | C25B—C28B | 1.540 (6) |
C25A—C26A | 1.528 (5) | C26B—H26D | 0.9600 |
C25A—C27A | 1.545 (5) | C26B—H26E | 0.9600 |
C26A—H26A | 0.9600 | C26B—H26F | 0.9600 |
C26A—H26B | 0.9600 | C27B—H27D | 0.9600 |
C26A—H26C | 0.9600 | C27B—H27E | 0.9600 |
C27A—H27A | 0.9600 | C27B—H27F | 0.9600 |
C27A—H27B | 0.9600 | C28B—H28D | 0.9600 |
C27A—H27C | 0.9600 | C28B—H28E | 0.9600 |
C28A—H28A | 0.9600 | C28B—H28F | 0.9600 |
C28A—H28B | 0.9600 | C29B—H29D | 0.9600 |
C28A—H28C | 0.9600 | C29B—H29E | 0.9600 |
Mn1B—O2B | 1.865 (2) | C29B—H29F | 0.9600 |
Mn1B—O1B | 1.882 (2) | ||
O1A—Mn1A—O2A | 91.85 (10) | O2B—Mn1B—N2B | 92.16 (11) |
O1A—Mn1A—N2A | 171.88 (12) | O1B—Mn1B—N2B | 171.75 (11) |
O2A—Mn1A—N2A | 92.91 (11) | N1B—Mn1B—N2B | 81.67 (12) |
O1A—Mn1A—N1A | 92.10 (11) | O2B—Mn1B—O3B | 88.18 (11) |
O2A—Mn1A—N1A | 170.09 (12) | O1B—Mn1B—O3B | 89.86 (11) |
N2A—Mn1A—N1A | 82.19 (12) | N1B—Mn1B—O3B | 83.42 (11) |
O1A—Mn1A—O1WA | 90.91 (10) | N2B—Mn1B—O3B | 84.42 (11) |
O2A—Mn1A—O1WA | 86.48 (10) | O2B—Mn1B—Cl1B | 95.77 (8) |
N2A—Mn1A—O1WA | 82.82 (11) | O1B—Mn1B—Cl1B | 97.12 (9) |
N1A—Mn1A—O1WA | 84.37 (11) | N1B—Mn1B—Cl1B | 91.90 (9) |
O1A—Mn1A—Cl1A | 96.40 (9) | N2B—Mn1B—Cl1B | 88.18 (9) |
O2A—Mn1A—Cl1A | 99.22 (8) | O3B—Mn1B—Cl1B | 171.74 (8) |
N2A—Mn1A—Cl1A | 89.33 (9) | C1B—O1B—Mn1B | 131.2 (2) |
N1A—Mn1A—Cl1A | 89.37 (9) | C20B—O2B—Mn1B | 131.5 (2) |
O1WA—Mn1A—Cl1A | 170.55 (7) | C29B—O3B—Mn1B | 130.4 (3) |
C1A—O1A—Mn1A | 132.0 (2) | C29B—O3B—H1O3 | 118.3 |
C20A—O2A—Mn1A | 130.3 (2) | Mn1B—O3B—H1O3 | 111.2 |
Mn1A—O1WA—H1WA | 136.5 | C7B—N1B—C8B | 121.3 (3) |
Mn1A—O1WA—H2WA | 113.8 | C7B—N1B—Mn1B | 124.7 (2) |
H1WA—O1WA—H2WA | 107.7 | C8B—N1B—Mn1B | 114.0 (2) |
C7A—N1A—C8A | 121.9 (3) | C14B—N2B—C13B | 122.2 (3) |
C7A—N1A—Mn1A | 124.2 (2) | C14B—N2B—Mn1B | 124.5 (2) |
C8A—N1A—Mn1A | 113.8 (2) | C13B—N2B—Mn1B | 113.3 (2) |
C14A—N2A—C13A | 122.1 (3) | O1B—C1B—C6B | 122.1 (3) |
C14A—N2A—Mn1A | 124.2 (2) | O1B—C1B—C2B | 119.7 (3) |
C13A—N2A—Mn1A | 113.7 (2) | C6B—C1B—C2B | 118.2 (3) |
O1A—C1A—C6A | 121.0 (3) | C3B—C2B—C1B | 117.8 (3) |
O1A—C1A—C2A | 119.5 (3) | C3B—C2B—C21B | 121.4 (3) |
C6A—C1A—C2A | 119.5 (3) | C1B—C2B—C21B | 120.8 (3) |
C3A—C2A—C1A | 117.0 (3) | C4B—C3B—C2B | 123.7 (3) |
C3A—C2A—C21A | 122.2 (3) | C4B—C3B—H3BA | 118.2 |
C1A—C2A—C21A | 120.8 (3) | C2B—C3B—H3BA | 118.2 |
C2A—C3A—C4A | 123.9 (4) | C5B—C4B—C3B | 118.9 (4) |
C2A—C3A—H3AA | 118.0 | C5B—C4B—H4BA | 120.5 |
C4A—C3A—H3AA | 118.0 | C3B—C4B—H4BA | 120.5 |
C5A—C4A—C3A | 119.1 (4) | C4B—C5B—C6B | 120.3 (4) |
C5A—C4A—H4AA | 120.4 | C4B—C5B—H5BA | 119.8 |
C3A—C4A—H4AA | 120.4 | C6B—C5B—H5BA | 119.8 |
C4A—C5A—C6A | 120.7 (3) | C5B—C6B—C1B | 121.1 (3) |
C4A—C5A—H5AA | 119.6 | C5B—C6B—C7B | 116.0 (3) |
C6A—C5A—H5AA | 119.6 | C1B—C6B—C7B | 122.9 (3) |
C5A—C6A—C1A | 119.5 (3) | N1B—C7B—C6B | 126.8 (3) |
C5A—C6A—C7A | 116.9 (3) | N1B—C7B—H7BA | 116.6 |
C1A—C6A—C7A | 123.5 (3) | C6B—C7B—H7BA | 116.6 |
N1A—C7A—C6A | 126.6 (3) | C9B—C8B—C13B | 120.6 (3) |
N1A—C7A—H7AA | 116.7 | C9B—C8B—N1B | 125.0 (3) |
C6A—C7A—H7AA | 116.7 | C13B—C8B—N1B | 114.5 (3) |
C9A—C8A—C13A | 120.0 (3) | C10B—C9B—C8B | 119.2 (4) |
C9A—C8A—N1A | 125.4 (3) | C10B—C9B—H9BA | 120.4 |
C13A—C8A—N1A | 114.6 (3) | C8B—C9B—H9BA | 120.4 |
C8A—C9A—C10A | 119.7 (4) | C9B—C10B—C11B | 120.3 (3) |
C8A—C9A—H9AA | 120.2 | C9B—C10B—H10B | 119.9 |
C10A—C9A—H9AA | 120.2 | C11B—C10B—H10B | 119.9 |
C9A—C10A—C11A | 120.3 (4) | C12B—C11B—C10B | 120.5 (3) |
C9A—C10A—H10A | 119.9 | C12B—C11B—H11B | 119.8 |
C11A—C10A—H10A | 119.9 | C10B—C11B—H11B | 119.8 |
C12A—C11A—C10A | 120.8 (4) | C11B—C12B—C13B | 120.4 (4) |
C12A—C11A—H11A | 119.6 | C11B—C12B—H12B | 119.8 |
C10A—C11A—H11A | 119.6 | C13B—C12B—H12B | 119.8 |
C11A—C12A—C13A | 119.8 (4) | C12B—C13B—C8B | 119.1 (3) |
C11A—C12A—H12A | 120.1 | C12B—C13B—N2B | 125.4 (3) |
C13A—C12A—H12A | 120.1 | C8B—C13B—N2B | 115.5 (3) |
C12A—C13A—C8A | 119.4 (3) | N2B—C14B—C15B | 126.1 (3) |
C12A—C13A—N2A | 125.8 (3) | N2B—C14B—H14B | 117.0 |
C8A—C13A—N2A | 114.9 (3) | C15B—C14B—H14B | 117.0 |
N2A—C14A—C15A | 126.3 (3) | C16B—C15B—C14B | 116.7 (3) |
N2A—C14A—H14A | 116.9 | C16B—C15B—C20B | 119.0 (3) |
C15A—C14A—H14A | 116.9 | C14B—C15B—C20B | 124.3 (3) |
C16A—C15A—C14A | 116.9 (3) | C17B—C16B—C15B | 121.5 (3) |
C16A—C15A—C20A | 119.1 (3) | C17B—C16B—H16B | 119.3 |
C14A—C15A—C20A | 124.0 (3) | C15B—C16B—H16B | 119.3 |
C17A—C16A—C15A | 120.5 (3) | C16B—C17B—C18B | 119.2 (4) |
C17A—C16A—H16A | 119.7 | C16B—C17B—H17B | 120.4 |
C15A—C16A—H16A | 119.7 | C18B—C17B—H17B | 120.4 |
C16A—C17A—C18A | 119.3 (3) | C19B—C18B—C17B | 123.2 (3) |
C16A—C17A—H17A | 120.3 | C19B—C18B—H18B | 118.4 |
C18A—C17A—H17A | 120.3 | C17B—C18B—H18B | 118.4 |
C19A—C18A—C17A | 123.5 (3) | C18B—C19B—C20B | 117.6 (3) |
C19A—C18A—H18A | 118.3 | C18B—C19B—C25B | 121.3 (3) |
C17A—C18A—H18A | 118.3 | C20B—C19B—C25B | 121.1 (3) |
C18A—C19A—C20A | 116.9 (3) | O2B—C20B—C15B | 121.3 (3) |
C18A—C19A—C25A | 121.8 (3) | O2B—C20B—C19B | 119.2 (3) |
C20A—C19A—C25A | 121.2 (3) | C15B—C20B—C19B | 119.5 (3) |
O2A—C20A—C19A | 118.8 (3) | C24B—C21B—C22B | 108.1 (3) |
O2A—C20A—C15A | 121.1 (3) | C24B—C21B—C23B | 110.6 (3) |
C19A—C20A—C15A | 120.1 (3) | C22B—C21B—C23B | 107.3 (3) |
C23A—C21A—C22A | 107.6 (4) | C24B—C21B—C2B | 108.5 (3) |
C23A—C21A—C2A | 109.5 (3) | C22B—C21B—C2B | 111.6 (3) |
C22A—C21A—C2A | 111.7 (3) | C23B—C21B—C2B | 110.9 (3) |
C23A—C21A—C24A | 110.1 (4) | C21B—C22B—H22D | 109.5 |
C22A—C21A—C24A | 107.7 (3) | C21B—C22B—H22E | 109.5 |
C2A—C21A—C24A | 110.2 (3) | H22D—C22B—H22E | 109.5 |
C21A—C22A—H22A | 109.5 | C21B—C22B—H22F | 109.5 |
C21A—C22A—H22B | 109.5 | H22D—C22B—H22F | 109.5 |
H22A—C22A—H22B | 109.5 | H22E—C22B—H22F | 109.5 |
C21A—C22A—H22C | 109.5 | C21B—C23B—H23D | 109.5 |
H22A—C22A—H22C | 109.5 | C21B—C23B—H23E | 109.5 |
H22B—C22A—H22C | 109.5 | H23D—C23B—H23E | 109.5 |
C21A—C23A—H23A | 109.5 | C21B—C23B—H23F | 109.5 |
C21A—C23A—H23B | 109.5 | H23D—C23B—H23F | 109.5 |
H23A—C23A—H23B | 109.5 | H23E—C23B—H23F | 109.5 |
C21A—C23A—H23C | 109.5 | C21B—C24B—H24D | 109.5 |
H23A—C23A—H23C | 109.5 | C21B—C24B—H24E | 109.5 |
H23B—C23A—H23C | 109.5 | H24D—C24B—H24E | 109.5 |
C21A—C24A—H24A | 109.5 | C21B—C24B—H24F | 109.5 |
C21A—C24A—H24B | 109.5 | H24D—C24B—H24F | 109.5 |
H24A—C24A—H24B | 109.5 | H24E—C24B—H24F | 109.5 |
C21A—C24A—H24C | 109.5 | C27B—C25B—C19B | 112.2 (3) |
H24A—C24A—H24C | 109.5 | C27B—C25B—C26B | 107.5 (3) |
H24B—C24A—H24C | 109.5 | C19B—C25B—C26B | 109.5 (3) |
C28A—C25A—C26A | 109.4 (3) | C27B—C25B—C28B | 107.4 (3) |
C28A—C25A—C19A | 109.7 (3) | C19B—C25B—C28B | 109.8 (3) |
C26A—C25A—C19A | 111.8 (3) | C26B—C25B—C28B | 110.3 (3) |
C28A—C25A—C27A | 107.0 (3) | C25B—C26B—H26D | 109.5 |
C26A—C25A—C27A | 107.3 (3) | C25B—C26B—H26E | 109.5 |
C19A—C25A—C27A | 111.5 (3) | H26D—C26B—H26E | 109.5 |
C25A—C26A—H26A | 109.5 | C25B—C26B—H26F | 109.5 |
C25A—C26A—H26B | 109.5 | H26D—C26B—H26F | 109.5 |
H26A—C26A—H26B | 109.5 | H26E—C26B—H26F | 109.5 |
C25A—C26A—H26C | 109.5 | C25B—C27B—H27D | 109.5 |
H26A—C26A—H26C | 109.5 | C25B—C27B—H27E | 109.5 |
H26B—C26A—H26C | 109.5 | H27D—C27B—H27E | 109.5 |
C25A—C27A—H27A | 109.5 | C25B—C27B—H27F | 109.5 |
C25A—C27A—H27B | 109.5 | H27D—C27B—H27F | 109.5 |
H27A—C27A—H27B | 109.5 | H27E—C27B—H27F | 109.5 |
C25A—C27A—H27C | 109.5 | C25B—C28B—H28D | 109.5 |
H27A—C27A—H27C | 109.5 | C25B—C28B—H28E | 109.5 |
H27B—C27A—H27C | 109.5 | H28D—C28B—H28E | 109.5 |
C25A—C28A—H28A | 109.5 | C25B—C28B—H28F | 109.5 |
C25A—C28A—H28B | 109.5 | H28D—C28B—H28F | 109.5 |
H28A—C28A—H28B | 109.5 | H28E—C28B—H28F | 109.5 |
C25A—C28A—H28C | 109.5 | O3B—C29B—H29D | 109.5 |
H28A—C28A—H28C | 109.5 | O3B—C29B—H29E | 109.5 |
H28B—C28A—H28C | 109.5 | H29D—C29B—H29E | 109.5 |
O2B—Mn1B—O1B | 93.60 (10) | O3B—C29B—H29F | 109.5 |
O2B—Mn1B—N1B | 170.00 (11) | H29D—C29B—H29F | 109.5 |
O1B—Mn1B—N1B | 91.79 (11) | H29E—C29B—H29F | 109.5 |
O2A—Mn1A—O1A—C1A | 171.6 (3) | O1B—Mn1B—O2B—C20B | −169.9 (3) |
N1A—Mn1A—O1A—C1A | 0.7 (3) | N1B—Mn1B—O2B—C20B | −47.5 (8) |
O1WA—Mn1A—O1A—C1A | 85.1 (3) | N2B—Mn1B—O2B—C20B | 4.1 (3) |
Cl1A—Mn1A—O1A—C1A | −88.9 (3) | O3B—Mn1B—O2B—C20B | −80.2 (3) |
O1A—Mn1A—O2A—C20A | −165.3 (3) | Cl1B—Mn1B—O2B—C20B | 92.5 (3) |
N2A—Mn1A—O2A—C20A | 8.2 (3) | O2B—Mn1B—O3B—C29B | −28.2 (4) |
O1WA—Mn1A—O2A—C20A | −74.5 (3) | O1B—Mn1B—O3B—C29B | 65.4 (4) |
Cl1A—Mn1A—O2A—C20A | 98.0 (3) | N1B—Mn1B—O3B—C29B | 157.3 (4) |
O1A—Mn1A—N1A—C7A | 5.4 (3) | N2B—Mn1B—O3B—C29B | −120.5 (4) |
N2A—Mn1A—N1A—C7A | −168.8 (3) | O2B—Mn1B—N1B—C7B | −116.6 (6) |
O1WA—Mn1A—N1A—C7A | −85.3 (3) | O1B—Mn1B—N1B—C7B | 6.0 (3) |
Cl1A—Mn1A—N1A—C7A | 101.8 (3) | N2B—Mn1B—N1B—C7B | −168.9 (3) |
O1A—Mn1A—N1A—C8A | −177.4 (2) | O3B—Mn1B—N1B—C7B | −83.6 (3) |
N2A—Mn1A—N1A—C8A | 8.4 (2) | Cl1B—Mn1B—N1B—C7B | 103.2 (3) |
O1WA—Mn1A—N1A—C8A | 91.9 (2) | O2B—Mn1B—N1B—C8B | 61.4 (8) |
Cl1A—Mn1A—N1A—C8A | −81.0 (2) | O1B—Mn1B—N1B—C8B | −176.0 (3) |
O2A—Mn1A—N2A—C14A | 1.6 (3) | N2B—Mn1B—N1B—C8B | 9.1 (2) |
N1A—Mn1A—N2A—C14A | 172.9 (3) | O3B—Mn1B—N1B—C8B | 94.4 (3) |
O1WA—Mn1A—N2A—C14A | 87.7 (3) | Cl1B—Mn1B—N1B—C8B | −78.8 (2) |
Cl1A—Mn1A—N2A—C14A | −97.6 (3) | O2B—Mn1B—N2B—C14B | −3.6 (3) |
O2A—Mn1A—N2A—C13A | −178.6 (2) | N1B—Mn1B—N2B—C14B | 168.5 (3) |
N1A—Mn1A—N2A—C13A | −7.2 (2) | O3B—Mn1B—N2B—C14B | 84.3 (3) |
O1WA—Mn1A—N2A—C13A | −92.5 (2) | Cl1B—Mn1B—N2B—C14B | −99.3 (3) |
Cl1A—Mn1A—N2A—C13A | 82.2 (2) | O2B—Mn1B—N2B—C13B | 179.1 (2) |
Mn1A—O1A—C1A—C6A | −6.9 (5) | N1B—Mn1B—N2B—C13B | −8.8 (2) |
Mn1A—O1A—C1A—C2A | 173.2 (3) | O3B—Mn1B—N2B—C13B | −93.0 (2) |
O1A—C1A—C2A—C3A | 174.9 (3) | Cl1B—Mn1B—N2B—C13B | 83.3 (2) |
C6A—C1A—C2A—C3A | −5.0 (5) | Mn1B—O1B—C1B—C6B | 7.2 (6) |
O1A—C1A—C2A—C21A | −5.1 (6) | Mn1B—O1B—C1B—C2B | −172.8 (3) |
C6A—C1A—C2A—C21A | 175.0 (4) | O1B—C1B—C2B—C3B | −178.1 (3) |
C1A—C2A—C3A—C4A | 2.9 (6) | C6B—C1B—C2B—C3B | 1.9 (6) |
C21A—C2A—C3A—C4A | −177.1 (4) | O1B—C1B—C2B—C21B | 3.4 (6) |
C2A—C3A—C4A—C5A | 0.2 (6) | C6B—C1B—C2B—C21B | −176.6 (3) |
C3A—C4A—C5A—C6A | −1.3 (6) | C1B—C2B—C3B—C4B | −0.4 (6) |
C4A—C5A—C6A—C1A | −0.8 (6) | C21B—C2B—C3B—C4B | 178.1 (4) |
C4A—C5A—C6A—C7A | 175.7 (3) | C2B—C3B—C4B—C5B | −0.9 (6) |
O1A—C1A—C6A—C5A | −175.8 (3) | C3B—C4B—C5B—C6B | 0.8 (6) |
C2A—C1A—C6A—C5A | 4.0 (5) | C4B—C5B—C6B—C1B | 0.7 (6) |
O1A—C1A—C6A—C7A | 7.9 (6) | C4B—C5B—C6B—C7B | 179.0 (4) |
C2A—C1A—C6A—C7A | −172.2 (4) | O1B—C1B—C6B—C5B | 177.9 (4) |
C8A—N1A—C7A—C6A | 177.3 (3) | C2B—C1B—C6B—C5B | −2.1 (6) |
Mn1A—N1A—C7A—C6A | −5.7 (5) | O1B—C1B—C6B—C7B | −0.2 (6) |
C5A—C6A—C7A—N1A | −177.8 (4) | C2B—C1B—C6B—C7B | 179.9 (4) |
C1A—C6A—C7A—N1A | −1.4 (6) | C8B—N1B—C7B—C6B | 179.9 (4) |
C7A—N1A—C8A—C9A | −10.7 (6) | Mn1B—N1B—C7B—C6B | −2.3 (6) |
Mn1A—N1A—C8A—C9A | 172.0 (3) | C5B—C6B—C7B—N1B | 179.8 (4) |
C7A—N1A—C8A—C13A | 169.2 (3) | C1B—C6B—C7B—N1B | −2.1 (6) |
Mn1A—N1A—C8A—C13A | −8.1 (4) | C7B—N1B—C8B—C9B | −10.6 (6) |
C13A—C8A—C9A—C10A | −1.0 (6) | Mn1B—N1B—C8B—C9B | 171.3 (3) |
N1A—C8A—C9A—C10A | 178.8 (4) | C7B—N1B—C8B—C13B | 170.3 (3) |
C8A—C9A—C10A—C11A | 0.1 (6) | Mn1B—N1B—C8B—C13B | −7.8 (4) |
C9A—C10A—C11A—C12A | 0.7 (6) | C13B—C8B—C9B—C10B | −0.8 (6) |
C10A—C11A—C12A—C13A | −0.4 (6) | N1B—C8B—C9B—C10B | −179.8 (4) |
C11A—C12A—C13A—C8A | −0.6 (5) | C8B—C9B—C10B—C11B | 0.3 (6) |
C11A—C12A—C13A—N2A | 178.6 (3) | C9B—C10B—C11B—C12B | 0.1 (6) |
C9A—C8A—C13A—C12A | 1.3 (5) | C10B—C11B—C12B—C13B | 0.0 (6) |
N1A—C8A—C13A—C12A | −178.6 (3) | C11B—C12B—C13B—C8B | −0.5 (6) |
C9A—C8A—C13A—N2A | −178.0 (3) | C11B—C12B—C13B—N2B | 179.2 (3) |
N1A—C8A—C13A—N2A | 2.1 (5) | C9B—C8B—C13B—C12B | 0.8 (6) |
C14A—N2A—C13A—C12A | 5.4 (6) | N1B—C8B—C13B—C12B | 180.0 (3) |
Mn1A—N2A—C13A—C12A | −174.4 (3) | C9B—C8B—C13B—N2B | −178.8 (3) |
C14A—N2A—C13A—C8A | −175.3 (3) | N1B—C8B—C13B—N2B | 0.4 (5) |
Mn1A—N2A—C13A—C8A | 4.9 (4) | C14B—N2B—C13B—C12B | 10.1 (6) |
C13A—N2A—C14A—C15A | 175.1 (3) | Mn1B—N2B—C13B—C12B | −172.5 (3) |
Mn1A—N2A—C14A—C15A | −5.1 (5) | C14B—N2B—C13B—C8B | −170.3 (3) |
N2A—C14A—C15A—C16A | −177.7 (4) | Mn1B—N2B—C13B—C8B | 7.1 (4) |
N2A—C14A—C15A—C20A | 0.0 (6) | C13B—N2B—C14B—C15B | 179.1 (3) |
C14A—C15A—C16A—C17A | 175.7 (4) | Mn1B—N2B—C14B—C15B | 2.0 (5) |
C20A—C15A—C16A—C17A | −2.1 (6) | N2B—C14B—C15B—C16B | −179.4 (4) |
C15A—C16A—C17A—C18A | −3.2 (6) | N2B—C14B—C15B—C20B | 0.8 (6) |
C16A—C17A—C18A—C19A | 2.7 (6) | C14B—C15B—C16B—C17B | 179.3 (4) |
C17A—C18A—C19A—C20A | 3.0 (6) | C20B—C15B—C16B—C17B | −0.8 (6) |
C17A—C18A—C19A—C25A | −172.9 (4) | C15B—C16B—C17B—C18B | 1.6 (6) |
Mn1A—O2A—C20A—C19A | 165.3 (3) | C16B—C17B—C18B—C19B | −0.8 (6) |
Mn1A—O2A—C20A—C15A | −14.3 (5) | C17B—C18B—C19B—C20B | −0.8 (6) |
C18A—C19A—C20A—O2A | 172.2 (3) | C17B—C18B—C19B—C25B | 178.9 (4) |
C25A—C19A—C20A—O2A | −11.8 (5) | Mn1B—O2B—C20B—C15B | −2.8 (5) |
C18A—C19A—C20A—C15A | −8.2 (5) | Mn1B—O2B—C20B—C19B | 177.6 (2) |
C25A—C19A—C20A—C15A | 167.7 (3) | C16B—C15B—C20B—O2B | 179.5 (3) |
C16A—C15A—C20A—O2A | −172.5 (3) | C14B—C15B—C20B—O2B | −0.6 (6) |
C14A—C15A—C20A—O2A | 9.8 (6) | C16B—C15B—C20B—C19B | −0.8 (5) |
C16A—C15A—C20A—C19A | 7.9 (5) | C14B—C15B—C20B—C19B | 179.1 (3) |
C14A—C15A—C20A—C19A | −169.7 (3) | C18B—C19B—C20B—O2B | −178.8 (3) |
C3A—C2A—C21A—C23A | 121.2 (4) | C25B—C19B—C20B—O2B | 1.5 (5) |
C1A—C2A—C21A—C23A | −58.8 (5) | C18B—C19B—C20B—C15B | 1.6 (5) |
C3A—C2A—C21A—C22A | 2.1 (6) | C25B—C19B—C20B—C15B | −178.1 (3) |
C1A—C2A—C21A—C22A | −177.9 (4) | C3B—C2B—C21B—C24B | −117.2 (4) |
C3A—C2A—C21A—C24A | −117.5 (4) | C1B—C2B—C21B—C24B | 61.2 (5) |
C1A—C2A—C21A—C24A | 62.5 (5) | C3B—C2B—C21B—C22B | 1.7 (5) |
C18A—C19A—C25A—C28A | 121.5 (4) | C1B—C2B—C21B—C22B | −179.9 (4) |
C20A—C19A—C25A—C28A | −54.2 (5) | C3B—C2B—C21B—C23B | 121.2 (4) |
C18A—C19A—C25A—C26A | −117.0 (4) | C1B—C2B—C21B—C23B | −60.4 (5) |
C20A—C19A—C25A—C26A | 67.3 (5) | C18B—C19B—C25B—C27B | 0.6 (5) |
C18A—C19A—C25A—C27A | 3.1 (5) | C20B—C19B—C25B—C27B | −179.8 (3) |
C20A—C19A—C25A—C27A | −172.6 (3) | C18B—C19B—C25B—C26B | −118.8 (4) |
O2B—Mn1B—O1B—C1B | 162.8 (3) | C20B—C19B—C25B—C26B | 60.9 (5) |
N1B—Mn1B—O1B—C1B | −8.8 (3) | C18B—C19B—C25B—C28B | 119.9 (4) |
O3B—Mn1B—O1B—C1B | 74.6 (3) | C20B—C19B—C25B—C28B | −60.4 (4) |
Cl1B—Mn1B—O1B—C1B | −100.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1WA—H2WA···Cl1B | 0.85 | 2.28 | 3.113 (3) | 167 |
O3B—H1O3···Cl1Ai | 1.00 | 2.06 | 3.026 (3) | 163 |
C5A—H5AA···O1WAii | 0.93 | 2.55 | 3.463 (5) | 169 |
C4B—H4BA···Cl1Aii | 0.93 | 2.79 | 3.528 (4) | 137 |
C12B—H12B···Cl1Aiii | 0.93 | 2.73 | 3.646 (4) | 170 |
C23A—H23C···O1A | 0.96 | 2.34 | 2.984 (6) | 124 |
C23B—H23E···O1B | 0.96 | 2.35 | 2.983 (5) | 123 |
C24A—H24C···O1A | 0.96 | 2.34 | 2.975 (5) | 123 |
C24B—H24E···O1B | 0.96 | 2.36 | 3.010 (5) | 124 |
C26A—H26A···O2A | 0.96 | 2.45 | 3.041 (5) | 119 |
C26B—H26E···O2B | 0.96 | 2.35 | 2.998 (5) | 124 |
C28A—H28A···O2A | 0.96 | 2.34 | 2.977 (5) | 124 |
C28B—H28F···O2B | 0.96 | 2.34 | 2.968 (5) | 122 |
C14B—H14B···Cg1iv | 0.93 | 3.23 | 3.690 (4) | 113 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+1, −y, −z; (iv) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C28H30N2O2)Cl(H2O)][Mn(C28H30N2O2)Cl(CH4O)] |
Mr | 1083.92 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 13.1080 (3), 13.8794 (3), 14.6085 (3) |
α, β, γ (°) | 95.177 (1), 99.996 (1), 95.639 (1) |
V (Å3) | 2589.08 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.65 |
Crystal size (mm) | 0.38 × 0.33 × 0.03 |
Data collection | |
Diffractometer | Bruker SMART APEX2 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.791, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37620, 10108, 6163 |
Rint | 0.076 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.147, 1.03 |
No. of reflections | 10108 |
No. of parameters | 653 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.57, −0.52 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O1WA—H2WA···Cl1B | 0.85 | 2.2806 | 3.113 (3) | 167 |
O3B—H1O3···Cl1Ai | 1.00 | 2.0564 | 3.026 (3) | 163 |
C5A—H5AA···O1WAii | 0.93 | 2.5468 | 3.463 (5) | 169 |
C4B—H4BA···Cl1Aii | 0.93 | 2.7918 | 3.528 (4) | 137 |
C12B—H12B···Cl1Aiii | 0.93 | 2.7262 | 3.646 (4) | 170 |
C23A—H23C···O1A | 0.96 | 2.3366 | 2.984 (6) | 124 |
C23B—H23E···O1B | 0.96 | 2.3462 | 2.983 (5) | 123 |
C24A—H24C···O1A | 0.96 | 2.3423 | 2.975 (5) | 123 |
C24B—H24E···O1B | 0.96 | 2.3633 | 3.010 (5) | 124 |
C26A—H26A···O2A | 0.96 | 2.4523 | 3.041 (5) | 119 |
C26B—H26E···O2B | 0.96 | 2.3493 | 2.998 (5) | 124 |
C28A—H28A···O2A | 0.96 | 2.3374 | 2.977 (5) | 124 |
C28B—H28F···O2B | 0.96 | 2.3417 | 2.968 (5) | 122 |
C14B—H14B···Cg1iv | 0.93 | 3.2322 | 3.690 (4) | 113 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z; (iii) −x+1, −y, −z; (iv) −x+2, −y, −z. |
Acknowledgements
The authors thank the Malaysian Government, Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia 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. The authors also thank Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) grant No. 203/PFIZIK/671064.
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Manganese complexes with Schiff base ligands have been of interest due to the variety of their applications in coordination chemistry, physics, catalysis and biological replication. They have been used as models for the oxygen-evolving complex of photosystem II (Glatzel et al., 2004), in catalysis (Dixit & Srinivasan, 1988), as single-molecule magnets (Lu et al., 2006) and serve as models for the active sites of manganese-containing metal enzymes (Stallings et al., 1985). We have previously reported the crystal structure of manganese complexes with Schiff base ligands containing oxygen and imine nitrogen atoms (Eltayeb et al., 2007; 2008). In this paper, we report the crystal structure of a Mn(III) complex of the closely related ligand {6,6'-di-tert-butyl-2,2'-[1,2-phenylenebis(nitrilomethylidene)]diphenolate.
The asymmetric unit of the title complex molecule (Fig. 1) contains two MnIII complexes (A and B) with the same Schiff base ligand. Coordination spheres around MnIII in both A and B are slightly distorted octahedra, with the coordination plane of each MnIII formed by the N2O2 donor atoms of the Schiff base. The axial positions in A are occupied by a Cl- ion and a water molecule whereas in B, these positions are occupied by a Cl- ion and a CH3OH molecule. The in-plane Mn—O distances are in the range 1.863 (2)–1.882 (2) Å with Mn—N distances 1.978 (3)–1.997 (3) Å, which fall in the range observed for six other MnIII coordination complexes of Schiff base ligands (Eltayeb et al., 2007; 2008; Habibi et al., 2007; Mitra et al., 2006). The elongation of the Mn—O and Mn—Cl axial bonds [2.402 (3) and 2.5420 (12) Å in A and 2.293 (3) and 2.5416 (11) Å in B] clearly indicate the usual Jahn Teller distortion of the MnIII oxidation state as has been found previously (Eltayeb et al., 2007; 2008; Habibi et al., 2007; Mitra et al., 2006). The basal bond angles O–Mn–O and O–Mn–N are close to 90° whereas the N–Mn–N angles are less than 90° [N1A–Mn1A–N2A = 82.19 (12)° and N1B–Mn1B–N2B = 81.67 (12)°]. The axial bond angle Cl–Mn–O is also less than the ideal value of 180° [170.55 (7)° in A and 171.74 (8)° in B]. Other bond lengths and angles observed in the structure are also normal (Allen et al., 1987). The coordinated water molecule of molecule A forms an O—H···Cl hydrogen bond with the coordinated Cl- ion of molecule B (Fig. 1). The dihedral angles between the two outer phenolate rings [(C1–C6) and C15–C20) of the tetradentate Schiff base ligand is 22.21 (19)° in A and 18.81 (19)° in B°. The central benzene ring (C8–C13) makes dihedral angles of 13.43 (19)° and 8.79 (19)° with the two outer phenolate rings in A [10.94° and 10.37 (19)° in B].
In the crystal structure (Fig. 2), O—H···Cl hydrogen bonds [O1WA—H2WA···Cl1B; symmetry code x, y, z and O3B—H1O3—Cl1A; symmetry code 1 + x, y, z) (Table 1)] link the MnIII complex molecules into infinite one-dimensional chains along the [1 0 0] direction. The crystal is stabilized by these O—H···Cl hydrogen bonds, together with weak C—H···O and C—H···Cl interactions and further stabilized by C—H···π interactions (Table 1); Cg1 is the centroid of the C8B–C13B benzene ring.