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The MnV complex in the title compound, (C8H20N)[Mn(C21H26N4O4)O], is inter­esting as it has been suggested that MnV oxospecies are inter­mediates both in epoxidation of alkenes and in water oxidation in PSII, i.e. photosystem II, the protein found in oxygenic photosynthetic organisms, which uses light to split water into O2, protons and electrons. The Mn atom has a square-pyramidal coordination of four N atoms with an apical O atom. The four N atoms coordinating to Mn [Mn-N = 1.872 (2)-1.882 (2) Å] form a plane within 0.03 (3) Å from which the Mn ion is displaced by 0.582 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047691/cv2305sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047691/cv2305Isup2.hkl
Contains datablock I

CCDC reference: 667124

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.044
  • wR factor = 0.073
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

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Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn - O5 .. 7.65 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn (4) 5.13
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

The title complex was prepared with the intention of testing a mechanism for oxygen-transfer discussed by e.g. Cavallo & Jacobsen (2003) as well as Linde et al. (1999) were the spin-state of the Mn-oxo species is supposed to dictate whether the reaction will proceed via a radical (from the triplet state) or metallacyclic intermediate (from the quintet-state). Since the title compound is isolated in a stable singlet-state it might be possible to selectively excite it to form either one or possibly both of these spin-states. Similar compounds have also been used as model complexes in the study of the water oxidizing enzyme, PSII (Weng et al., 2004). The oxidation state of the MnV atom was verified with bond valence calculations (Brown & Altermatt, 1985; Brown, 1996).

Related literature top

For general background, see: Collins et al. (1990, 1991); Cavallo & Jacobsen (2003); Linde et al. (1999). For the use of similar compounds as model compounds in PSII, see: Weng et al. (2004). The oxidation state of the Mn atom was verified according to Brown & Altermatt (1985) and Brown (1996).

Experimental top

The title compound was synthesized following literature procedures (Collins et al., 1990; 1991) and recrystallized from a CH2Cl2 solution by adding benzene as a layer upon the original solution and letting the benzene mix with the original solution by diffusion.

Refinement top

All hydrogen atoms were geometrically positioned (C—H 0.93–0.97 Å) and refined in riding mode approximation, with Uiso(H) = 1.5Ueq(C) for the CH3 and 1.2Ueq(C) for the CH2 and aromatic CH.

Structure description top

The title complex was prepared with the intention of testing a mechanism for oxygen-transfer discussed by e.g. Cavallo & Jacobsen (2003) as well as Linde et al. (1999) were the spin-state of the Mn-oxo species is supposed to dictate whether the reaction will proceed via a radical (from the triplet state) or metallacyclic intermediate (from the quintet-state). Since the title compound is isolated in a stable singlet-state it might be possible to selectively excite it to form either one or possibly both of these spin-states. Similar compounds have also been used as model complexes in the study of the water oxidizing enzyme, PSII (Weng et al., 2004). The oxidation state of the MnV atom was verified with bond valence calculations (Brown & Altermatt, 1985; Brown, 1996).

For general background, see: Collins et al. (1990, 1991); Cavallo & Jacobsen (2003); Linde et al. (1999). For the use of similar compounds as model compounds in PSII, see: Weng et al. (2004). The oxidation state of the Mn atom was verified according to Brown & Altermatt (1985) and Brown (1996).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The content of asymmetric part of the title compound with the atom numbering scheme and displacement ellipsoids drawn at the 50% probability level.
Tetraethylammonium [12,12-diethyl-2,2,9,9,-tetramethyl-1,4,7,10-tetraza-5,6-benzotridecane- 3,8,11,13-tetraone(4-)]oxidomanganate(V) top
Crystal data top
(C8H20N)[Mn(C21H26N4O4)O]Z = 4
Mr = 599.65F(000) = 1280
Monoclinic, P21/cDx = 1.290 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.2606 (11) Åθ = 3.8–33.4°
b = 15.5269 (15) ŵ = 0.47 mm1
c = 17.7586 (17) ÅT = 293 K
β = 96.024 (8)°Prism, red
V = 3087.8 (5) Å30.20 × 0.15 × 0.10 mm
Data collection top
Oxford Diffraction Xcalibur-3 kappa
diffractometer with SapphireIII CCD
5454 independent reflections
Radiation source: fine-focus sealed tube2197 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
Detector resolution: 12 pixels mm-1θmax = 25.0°, θmin = 1.8°
ω scans at different φh = 1313
Absorption correction: numerical
(X-RED; Stoe & Cie, 1997)
k = 1818
Tmin = 0.899, Tmax = 0.960l = 2121
18232 measured reflections
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H-atom parameters constrained
S = 0.82 w = 1/[σ2(Fo2) + (0.0259P)2]
where P = (Fo2 + 2Fc2)/3
5454 reflections(Δ/σ)max < 0.001
361 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
(C8H20N)[Mn(C21H26N4O4)O]V = 3087.8 (5) Å3
Mr = 599.65Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.2606 (11) ŵ = 0.47 mm1
b = 15.5269 (15) ÅT = 293 K
c = 17.7586 (17) Å0.20 × 0.15 × 0.10 mm
β = 96.024 (8)°
Data collection top
Oxford Diffraction Xcalibur-3 kappa
diffractometer with SapphireIII CCD
5454 independent reflections
Absorption correction: numerical
(X-RED; Stoe & Cie, 1997)
2197 reflections with I > 2σ(I)
Tmin = 0.899, Tmax = 0.960Rint = 0.078
18232 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.074H-atom parameters constrained
S = 0.82Δρmax = 0.24 e Å3
5454 reflectionsΔρmin = 0.26 e Å3
361 parameters
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
C10.0713 (3)0.1659 (2)0.64612 (19)0.0536 (10)
C20.0228 (3)0.1642 (2)0.70234 (19)0.0494 (9)
C30.0040 (4)0.1197 (2)0.77932 (18)0.0487 (10)
C40.1351 (3)0.0566 (2)0.88100 (16)0.0473 (9)
C50.2652 (3)0.0322 (2)0.89271 (19)0.0566 (10)
C60.4369 (3)0.00699 (19)0.82099 (19)0.0470 (9)
C70.5237 (3)0.0231 (2)0.87699 (19)0.0574 (10)
H70.50440.03410.92570.069*
C80.6371 (3)0.0360 (2)0.8587 (2)0.0671 (11)
H80.69500.05550.89600.080*
C90.6687 (3)0.0210 (2)0.7866 (2)0.0698 (12)
H90.74650.03120.77570.084*
C100.5833 (3)0.0093 (2)0.73066 (19)0.0575 (10)
H100.60330.01980.68200.069*
C110.4679 (3)0.0237 (2)0.74835 (19)0.0474 (9)
C120.3802 (4)0.0999 (2)0.63519 (19)0.0578 (11)
C130.2646 (3)0.1429 (2)0.60455 (18)0.0539 (10)
C140.2923 (3)0.2382 (2)0.59448 (17)0.0780 (12)
H14A0.22080.26790.57500.117*
H14B0.35140.24420.55960.117*
H14C0.32210.26250.64250.117*
C150.2206 (3)0.0987 (2)0.52830 (16)0.0861 (13)
H15A0.14750.12500.50720.129*
H15B0.20720.03860.53690.129*
H15C0.28010.10500.49370.129*
C160.1365 (3)0.1231 (2)0.66216 (18)0.0666 (11)
H16A0.19840.12420.69630.080*
H16B0.16390.15790.61830.080*
C170.1203 (3)0.0311 (2)0.63653 (18)0.0866 (12)
H17A0.19450.00990.61190.130*
H17B0.09550.00420.67970.130*
H17C0.06060.02950.60180.130*
C180.0493 (3)0.2593 (2)0.72047 (19)0.0738 (12)
H18A0.07580.28900.67360.089*
H18B0.11420.26120.75230.089*
C190.0576 (4)0.3070 (2)0.7601 (2)0.0905 (14)
H19A0.03540.36530.76970.136*
H19B0.12160.30660.72850.136*
H19C0.08310.27900.80730.136*
C200.1145 (3)0.1258 (2)0.93946 (15)0.0658 (11)
H20A0.03200.14270.93380.099*
H20B0.16360.17500.93180.099*
H20C0.13510.10340.98950.099*
C210.0643 (3)0.0252 (2)0.89443 (17)0.0766 (12)
H21A0.01960.01260.88780.115*
H21B0.08600.04560.94500.115*
H21C0.08200.06870.85890.115*
N10.1796 (3)0.12924 (16)0.66200 (13)0.0449 (7)
N20.3707 (2)0.05739 (16)0.70151 (14)0.0455 (7)
N30.3167 (2)0.02626 (15)0.82645 (13)0.0447 (7)
N40.1136 (2)0.08759 (15)0.80135 (13)0.0429 (7)
O30.3189 (2)0.01663 (18)0.95520 (12)0.1030 (10)
O40.4708 (2)0.10505 (17)0.60263 (13)0.0946 (10)
O50.16898 (18)0.04408 (13)0.70485 (9)0.0552 (6)
O10.0409 (2)0.20457 (16)0.58588 (13)0.0806 (8)
O20.0786 (2)0.11887 (14)0.82048 (12)0.0658 (7)
Mn0.21949 (5)0.04441 (3)0.73523 (2)0.04636 (17)
N50.6263 (3)0.24009 (18)0.40445 (14)0.0504 (8)
C220.5082 (3)0.1965 (2)0.40647 (19)0.0751 (12)
H22A0.50300.17530.45740.090*
H22B0.50530.14700.37300.090*
C230.3988 (3)0.2534 (3)0.3835 (2)0.1245 (18)
H23A0.32730.22040.38620.187*
H23B0.40160.27360.33260.187*
H23C0.39910.30170.41720.187*
C240.6415 (4)0.3134 (2)0.46178 (18)0.0798 (13)
H24A0.71590.34280.45580.096*
H24B0.57720.35440.44990.096*
C250.6422 (4)0.2870 (2)0.54408 (16)0.0951 (14)
H25A0.65280.33710.57580.143*
H25B0.70660.24740.55710.143*
H25C0.56780.25980.55140.143*
C260.7197 (3)0.1717 (2)0.42219 (18)0.0657 (11)
H26A0.70430.14380.46910.079*
H26B0.70980.12860.38250.079*
C270.8479 (3)0.2010 (3)0.43007 (19)0.0993 (14)
H27A0.89940.15240.44140.149*
H27B0.86030.24230.47030.149*
H27C0.86590.22700.38350.149*
C280.6357 (3)0.2807 (2)0.32739 (16)0.0650 (11)
H28A0.57860.32760.32060.078*
H28B0.71480.30540.32740.078*
C290.6142 (3)0.2206 (2)0.26035 (16)0.0801 (13)
H29A0.62260.25180.21460.120*
H29B0.53500.19730.25840.120*
H29C0.67140.17460.26560.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.054 (3)0.056 (3)0.048 (2)0.004 (2)0.007 (2)0.0051 (19)
C20.046 (3)0.044 (3)0.056 (2)0.000 (2)0.004 (2)0.0021 (19)
C30.058 (3)0.043 (2)0.044 (2)0.001 (2)0.001 (2)0.0091 (18)
C40.047 (2)0.055 (3)0.039 (2)0.010 (2)0.0029 (18)0.0039 (19)
C50.054 (3)0.071 (3)0.044 (2)0.013 (2)0.003 (2)0.001 (2)
C60.047 (3)0.044 (2)0.049 (2)0.000 (2)0.001 (2)0.0018 (18)
C70.055 (3)0.059 (3)0.055 (2)0.003 (2)0.006 (2)0.0045 (19)
C80.052 (3)0.070 (3)0.076 (3)0.007 (3)0.009 (2)0.004 (2)
C90.042 (3)0.078 (3)0.090 (3)0.005 (2)0.009 (3)0.011 (2)
C100.051 (3)0.063 (3)0.059 (2)0.002 (2)0.008 (2)0.0031 (19)
C110.039 (2)0.049 (3)0.054 (2)0.001 (2)0.004 (2)0.0086 (19)
C120.058 (3)0.067 (3)0.049 (2)0.000 (2)0.010 (2)0.001 (2)
C130.058 (3)0.062 (3)0.041 (2)0.001 (2)0.000 (2)0.0075 (19)
C140.082 (3)0.073 (3)0.080 (3)0.006 (3)0.008 (2)0.029 (2)
C150.097 (3)0.117 (3)0.043 (2)0.008 (3)0.004 (2)0.006 (2)
C160.056 (3)0.076 (3)0.064 (2)0.003 (3)0.009 (2)0.003 (2)
C170.079 (3)0.095 (4)0.082 (3)0.020 (3)0.006 (2)0.021 (3)
C180.072 (3)0.060 (3)0.087 (3)0.012 (3)0.002 (3)0.005 (2)
C190.084 (3)0.056 (3)0.129 (4)0.003 (3)0.005 (3)0.015 (3)
C200.067 (3)0.090 (3)0.041 (2)0.001 (2)0.007 (2)0.013 (2)
C210.095 (3)0.072 (3)0.063 (2)0.007 (3)0.012 (2)0.009 (2)
N10.0452 (19)0.0511 (19)0.0373 (16)0.0060 (17)0.0008 (15)0.0063 (13)
N20.0458 (19)0.0526 (19)0.0380 (15)0.0024 (17)0.0044 (15)0.0053 (15)
N30.0414 (19)0.053 (2)0.0387 (16)0.0088 (16)0.0007 (14)0.0012 (14)
N40.043 (2)0.051 (2)0.0339 (15)0.0022 (16)0.0008 (15)0.0016 (13)
O30.090 (2)0.176 (3)0.0399 (14)0.044 (2)0.0057 (14)0.0171 (16)
O40.074 (2)0.134 (2)0.0805 (19)0.0175 (19)0.0307 (18)0.0368 (17)
O50.0587 (15)0.0472 (14)0.0583 (13)0.0089 (14)0.0008 (11)0.0127 (13)
O10.072 (2)0.102 (2)0.0652 (16)0.0138 (17)0.0053 (15)0.0302 (15)
O20.0459 (16)0.0950 (19)0.0568 (15)0.0063 (15)0.0070 (13)0.0018 (14)
Mn0.0484 (3)0.0494 (4)0.0399 (3)0.0004 (3)0.0018 (2)0.0004 (3)
N50.059 (2)0.041 (2)0.0513 (18)0.0051 (18)0.0048 (16)0.0071 (15)
C220.060 (3)0.095 (3)0.071 (3)0.000 (3)0.011 (2)0.017 (2)
C230.062 (3)0.193 (5)0.121 (4)0.028 (4)0.017 (3)0.043 (3)
C240.115 (4)0.052 (3)0.071 (3)0.012 (3)0.002 (3)0.006 (2)
C250.139 (4)0.098 (3)0.047 (2)0.019 (3)0.006 (3)0.010 (2)
C260.069 (3)0.063 (3)0.065 (2)0.014 (3)0.008 (2)0.007 (2)
C270.062 (3)0.159 (4)0.075 (3)0.004 (3)0.003 (2)0.021 (3)
C280.074 (3)0.067 (3)0.054 (2)0.001 (2)0.001 (2)0.019 (2)
C290.089 (3)0.098 (3)0.052 (2)0.003 (3)0.002 (2)0.000 (2)
Geometric parameters (Å, º) top
C1—O11.243 (3)C18—H18A0.9700
C1—N11.348 (4)C18—H18B0.9700
C1—C21.531 (4)C19—H19A0.9600
C2—C31.533 (4)C19—H19B0.9600
C2—C161.537 (4)C19—H19C0.9600
C2—C181.548 (4)C20—H20A0.9600
C3—O21.242 (3)C20—H20B0.9600
C3—N41.350 (4)C20—H20C0.9600
C4—N41.490 (3)C21—H21A0.9600
C4—C51.507 (4)C21—H21B0.9600
C4—C201.529 (4)C21—H21C0.9600
C4—C211.531 (4)N1—Mn1.872 (2)
C5—O31.231 (3)N2—Mn1.874 (2)
C5—N31.369 (3)N3—Mn1.879 (2)
C6—C111.396 (4)N4—Mn1.882 (2)
C6—N31.399 (4)O5—Mn1.561 (2)
C6—C71.399 (4)N5—C221.495 (4)
C7—C81.365 (4)N5—C261.505 (4)
C7—H70.9300N5—C281.521 (3)
C8—C91.384 (4)N5—C241.525 (4)
C8—H80.9300C22—C231.536 (4)
C9—C101.391 (4)C22—H22A0.9700
C9—H90.9300C22—H22B0.9700
C10—C111.386 (4)C23—H23A0.9600
C10—H100.9300C23—H23B0.9600
C11—N21.405 (4)C23—H23C0.9600
C12—O41.227 (4)C24—C251.517 (4)
C12—N21.364 (4)C24—H24A0.9700
C12—C131.513 (4)C24—H24B0.9700
C13—N11.486 (4)C25—H25A0.9600
C13—C141.526 (4)C25—H25B0.9600
C13—C151.552 (4)C25—H25C0.9600
C14—H14A0.9600C26—C271.507 (4)
C14—H14B0.9600C26—H26A0.9700
C14—H14C0.9600C26—H26B0.9700
C15—H15A0.9600C27—H27A0.9600
C15—H15B0.9600C27—H27B0.9600
C15—H15C0.9600C27—H27C0.9600
C16—C171.516 (4)C28—C291.512 (4)
C16—H16A0.9700C28—H28A0.9700
C16—H16B0.9700C28—H28B0.9700
C17—H17A0.9600C29—H29A0.9600
C17—H17B0.9600C29—H29B0.9600
C17—H17C0.9600C29—H29C0.9600
C18—C191.521 (4)
O1—C1—N1123.1 (3)H20A—C20—H20B109.5
O1—C1—C2115.0 (3)C4—C20—H20C109.5
N1—C1—C2121.9 (3)H20A—C20—H20C109.5
C1—C2—C3120.3 (3)H20B—C20—H20C109.5
C1—C2—C16107.8 (3)C4—C21—H21A109.5
C3—C2—C16107.7 (3)C4—C21—H21B109.5
C1—C2—C18106.3 (3)H21A—C21—H21B109.5
C3—C2—C18105.6 (3)C4—C21—H21C109.5
C16—C2—C18108.8 (3)H21A—C21—H21C109.5
O2—C3—N4123.0 (3)H21B—C21—H21C109.5
O2—C3—C2116.1 (3)C1—N1—C13115.4 (3)
N4—C3—C2120.9 (3)C1—N1—Mn126.1 (2)
N4—C4—C5105.7 (3)C13—N1—Mn116.9 (2)
N4—C4—C20113.3 (3)C12—N2—C11124.3 (3)
C5—C4—C20107.3 (3)C12—N2—Mn119.0 (2)
N4—C4—C21112.4 (3)C11—N2—Mn116.7 (2)
C5—C4—C21106.6 (3)C5—N3—C6125.0 (3)
C20—C4—C21111.0 (3)C5—N3—Mn118.0 (2)
O3—C5—N3123.3 (3)C6—N3—Mn116.9 (2)
O3—C5—C4123.5 (3)C3—N4—C4116.5 (3)
N3—C5—C4113.1 (3)C3—N4—Mn124.8 (2)
C11—C6—N3111.2 (3)C4—N4—Mn115.3 (2)
C11—C6—C7119.7 (3)O5—Mn—N1109.08 (10)
N3—C6—C7129.1 (3)O5—Mn—N2107.12 (10)
C8—C7—C6118.8 (3)N1—Mn—N282.09 (12)
C8—C7—H7120.6O5—Mn—N3108.91 (10)
C6—C7—H7120.6N1—Mn—N3141.27 (11)
C7—C8—C9122.2 (3)N2—Mn—N379.91 (12)
C7—C8—H8118.9O5—Mn—N4107.30 (10)
C9—C8—H8118.9N1—Mn—N493.50 (12)
C8—C9—C10119.5 (3)N2—Mn—N4144.80 (11)
C8—C9—H9120.3N3—Mn—N482.27 (12)
C10—C9—H9120.3C22—N5—C26106.2 (3)
C11—C10—C9119.1 (3)C22—N5—C28110.9 (3)
C11—C10—H10120.4C26—N5—C28111.6 (3)
C9—C10—H10120.4C22—N5—C24111.1 (3)
C10—C11—C6120.7 (3)C26—N5—C24111.1 (3)
C10—C11—N2128.1 (3)C28—N5—C24106.1 (2)
C6—C11—N2111.2 (3)N5—C22—C23115.0 (3)
O4—C12—N2125.6 (4)N5—C22—H22A108.5
O4—C12—C13121.9 (3)C23—C22—H22A108.5
N2—C12—C13112.4 (3)N5—C22—H22B108.5
N1—C13—C12106.4 (3)C23—C22—H22B108.5
N1—C13—C14111.9 (3)H22A—C22—H22B107.5
C12—C13—C14106.9 (3)C22—C23—H23A109.5
N1—C13—C15111.5 (3)C22—C23—H23B109.5
C12—C13—C15107.5 (3)H23A—C23—H23B109.5
C14—C13—C15112.2 (3)C22—C23—H23C109.5
C13—C14—H14A109.5H23A—C23—H23C109.5
C13—C14—H14B109.5H23B—C23—H23C109.5
H14A—C14—H14B109.5C25—C24—N5115.5 (3)
C13—C14—H14C109.5C25—C24—H24A108.4
H14A—C14—H14C109.5N5—C24—H24A108.4
H14B—C14—H14C109.5C25—C24—H24B108.4
C13—C15—H15A109.5N5—C24—H24B108.4
C13—C15—H15B109.5H24A—C24—H24B107.5
H15A—C15—H15B109.5C24—C25—H25A109.5
C13—C15—H15C109.5C24—C25—H25B109.5
H15A—C15—H15C109.5H25A—C25—H25B109.5
H15B—C15—H15C109.5C24—C25—H25C109.5
C17—C16—C2114.1 (3)H25A—C25—H25C109.5
C17—C16—H16A108.7H25B—C25—H25C109.5
C2—C16—H16A108.7C27—C26—N5116.6 (3)
C17—C16—H16B108.7C27—C26—H26A108.1
C2—C16—H16B108.7N5—C26—H26A108.1
H16A—C16—H16B107.6C27—C26—H26B108.1
C16—C17—H17A109.5N5—C26—H26B108.1
C16—C17—H17B109.5H26A—C26—H26B107.3
H17A—C17—H17B109.5C26—C27—H27A109.5
C16—C17—H17C109.5C26—C27—H27B109.5
H17A—C17—H17C109.5H27A—C27—H27B109.5
H17B—C17—H17C109.5C26—C27—H27C109.5
C19—C18—C2113.6 (3)H27A—C27—H27C109.5
C19—C18—H18A108.9H27B—C27—H27C109.5
C2—C18—H18A108.9C29—C28—N5115.6 (3)
C19—C18—H18B108.9C29—C28—H28A108.4
C2—C18—H18B108.9N5—C28—H28A108.4
H18A—C18—H18B107.7C29—C28—H28B108.4
C18—C19—H19A109.5N5—C28—H28B108.4
C18—C19—H19B109.5H28A—C28—H28B107.4
H19A—C19—H19B109.5C28—C29—H29A109.5
C18—C19—H19C109.5C28—C29—H29B109.5
H19A—C19—H19C109.5H29A—C29—H29B109.5
H19B—C19—H19C109.5C28—C29—H29C109.5
C4—C20—H20A109.5H29A—C29—H29C109.5
C4—C20—H20B109.5H29B—C29—H29C109.5
O1—C1—C2—C3179.1 (3)O3—C5—N3—Mn175.7 (3)
N1—C1—C2—C30.2 (5)C4—C5—N3—Mn2.3 (4)
O1—C1—C2—C1657.1 (4)C11—C6—N3—C5167.2 (3)
N1—C1—C2—C16124.0 (3)C7—C6—N3—C511.2 (5)
O1—C1—C2—C1859.4 (4)C11—C6—N3—Mn13.3 (3)
N1—C1—C2—C18119.5 (3)C7—C6—N3—Mn168.3 (3)
C1—C2—C3—O2177.8 (3)O2—C3—N4—C44.7 (5)
C16—C2—C3—O254.0 (4)C2—C3—N4—C4171.9 (3)
C18—C2—C3—O262.2 (4)O2—C3—N4—Mn153.3 (2)
C1—C2—C3—N45.4 (5)C2—C3—N4—Mn30.1 (4)
C16—C2—C3—N4129.3 (3)C5—C4—N4—C3175.0 (3)
C18—C2—C3—N4114.6 (3)C20—C4—N4—C357.8 (4)
N4—C4—C5—O3168.2 (3)C21—C4—N4—C369.2 (4)
C20—C4—C5—O347.0 (5)C5—C4—N4—Mn24.9 (3)
C21—C4—C5—O372.1 (4)C20—C4—N4—Mn142.2 (2)
N4—C4—C5—N313.9 (4)C21—C4—N4—Mn90.9 (3)
C20—C4—C5—N3135.1 (3)C1—N1—Mn—O576.3 (3)
C21—C4—C5—N3105.9 (3)C13—N1—Mn—O588.5 (2)
C11—C6—C7—C80.5 (5)C1—N1—Mn—N2178.3 (3)
N3—C6—C7—C8178.8 (3)C13—N1—Mn—N216.9 (2)
C6—C7—C8—C90.6 (5)C1—N1—Mn—N3115.4 (3)
C7—C8—C9—C100.9 (5)C13—N1—Mn—N379.8 (3)
C8—C9—C10—C110.2 (5)C1—N1—Mn—N433.4 (3)
C9—C10—C11—C60.9 (5)C13—N1—Mn—N4161.8 (2)
C9—C10—C11—N2177.0 (3)C12—N2—Mn—O593.0 (2)
N3—C6—C11—C10179.8 (3)C11—N2—Mn—O588.5 (2)
C7—C6—C11—C101.2 (5)C12—N2—Mn—N114.6 (2)
N3—C6—C11—N21.5 (4)C11—N2—Mn—N1163.9 (2)
C7—C6—C11—N2177.0 (3)C12—N2—Mn—N3160.2 (2)
O4—C12—C13—N1175.0 (3)C11—N2—Mn—N318.3 (2)
N2—C12—C13—N14.2 (4)C12—N2—Mn—N499.4 (3)
O4—C12—C13—C1455.3 (4)C11—N2—Mn—N479.0 (3)
N2—C12—C13—C14124.0 (3)C5—N3—Mn—O592.2 (2)
O4—C12—C13—C1565.4 (5)C6—N3—Mn—O587.3 (2)
N2—C12—C13—C15115.3 (3)C5—N3—Mn—N199.5 (3)
C1—C2—C16—C1761.3 (4)C6—N3—Mn—N181.0 (3)
C3—C2—C16—C1769.8 (4)C5—N3—Mn—N2163.0 (2)
C18—C2—C16—C17176.2 (3)C6—N3—Mn—N217.4 (2)
C1—C2—C18—C1963.9 (4)C5—N3—Mn—N413.5 (2)
C3—C2—C18—C1965.0 (4)C6—N3—Mn—N4166.9 (2)
C16—C2—C18—C19179.7 (3)C3—N4—Mn—O572.7 (3)
O1—C1—N1—C134.0 (5)C4—N4—Mn—O585.6 (2)
C2—C1—N1—C13174.9 (3)C3—N4—Mn—N138.6 (3)
O1—C1—N1—Mn161.0 (2)C4—N4—Mn—N1163.2 (2)
C2—C1—N1—Mn20.1 (4)C3—N4—Mn—N2119.8 (3)
C12—C13—N1—C1177.7 (3)C4—N4—Mn—N282.0 (3)
C14—C13—N1—C161.2 (4)C3—N4—Mn—N3179.9 (3)
C15—C13—N1—C165.3 (4)C4—N4—Mn—N321.9 (2)
C12—C13—N1—Mn15.9 (3)C26—N5—C22—C23175.3 (3)
C14—C13—N1—Mn132.3 (2)C28—N5—C22—C2353.9 (4)
C15—C13—N1—Mn101.1 (3)C24—N5—C22—C2363.8 (4)
O4—C12—N2—C119.9 (5)C22—N5—C24—C2562.8 (4)
C13—C12—N2—C11169.4 (3)C26—N5—C24—C2555.2 (4)
O4—C12—N2—Mn171.8 (3)C28—N5—C24—C25176.6 (3)
C13—C12—N2—Mn9.0 (4)C22—N5—C26—C27175.1 (3)
C10—C11—N2—C1215.6 (5)C28—N5—C26—C2764.0 (4)
C6—C11—N2—C12162.5 (3)C24—N5—C26—C2754.2 (4)
C10—C11—N2—Mn166.0 (3)C22—N5—C28—C2955.0 (4)
C6—C11—N2—Mn15.9 (3)C26—N5—C28—C2963.1 (4)
O3—C5—N3—C63.8 (5)C24—N5—C28—C29175.7 (3)
C4—C5—N3—C6178.2 (3)

Experimental details

Crystal data
Chemical formula(C8H20N)[Mn(C21H26N4O4)O]
Mr599.65
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)11.2606 (11), 15.5269 (15), 17.7586 (17)
β (°) 96.024 (8)
V3)3087.8 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.47
Crystal size (mm)0.20 × 0.15 × 0.10
Data collection
DiffractometerOxford Diffraction Xcalibur-3 kappa
diffractometer with SapphireIII CCD
Absorption correctionNumerical
(X-RED; Stoe & Cie, 1997)
Tmin, Tmax0.899, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
18232, 5454, 2197
Rint0.078
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.074, 0.82
No. of reflections5454
No. of parameters361
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.26

Computer programs: CrysAlis CCD (Oxford Diffraction, 2003), CrysAlis RED (Oxford Diffraction, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Bergerhoff, 1996), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
N1—Mn1.872 (2)N4—Mn1.882 (2)
N2—Mn1.874 (2)O5—Mn1.561 (2)
N3—Mn1.879 (2)
O5—Mn—N1109.08 (10)N2—Mn—N379.91 (12)
O5—Mn—N2107.12 (10)O5—Mn—N4107.30 (10)
N1—Mn—N282.09 (12)N1—Mn—N493.50 (12)
O5—Mn—N3108.91 (10)N2—Mn—N4144.80 (11)
N1—Mn—N3141.27 (11)N3—Mn—N482.27 (12)
 

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