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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1270.
Published online 2010 September 18. doi:  10.1107/S1600536810036457
PMCID: PMC2983334

(Dimethyl­formamide)(2-methyl­propen­oato)[tris­(1-methyl-1H-benzimidazol-2-ylmeth­yl)amine]­manganese(II) perchlorate dimethyl­formamide solvate

Abstract

In the title complex, [Mn(C4H5O2)(C27H27N7)(C3H7NO)]ClO4·C3H7NO, the MnII ion is seven-coordinated in a distorted monocapped trigonal-prismatic geometry formed by a tetra­dentate tris­(1-methyl-1H-benzimidazol-2-ylmeth­yl)amine mol­ecule, a bidentate 2-methacrylate anion and a dimethyl­formamide mol­ecule. The methyl groups of the coordinated dimethyl­formamide mol­ecule and the perchlorate anions are disordered over two positions with occupancy factors of 0.640 (8) and 0.360 (8).

Related literature

For the biological activity of benzimidazole derivatives, see: Horton et al. (2003 [triangle]). For related structures, see: Wu et al. (2005 [triangle], 2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1270-scheme1.jpg

Experimental

Crystal data

  • [Mn(C4H5O2)(C27H27N7)(C3H7NO)]ClO4·C3H7NO
  • M r = 835.22
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1270-efi1.jpg
  • a = 12.139 (5) Å
  • b = 12.354 (5) Å
  • c = 15.146 (6) Å
  • α = 89.168 (4)°
  • β = 71.098 (4)°
  • γ = 76.936 (5)°
  • V = 2088.9 (14) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.44 mm−1
  • T = 296 K
  • 0.38 × 0.34 × 0.30 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS: Bruker, 2006 [triangle]) T min = 0.851, T max = 0.880
  • 15471 measured reflections
  • 7680 independent reflections
  • 5422 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.187
  • S = 1.10
  • 7680 reflections
  • 525 parameters
  • 8 restraints
  • H-atom parameters constrained
  • Δρmax = 0.90 e Å−3
  • Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036457/is2590sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036457/is2590Isup2.hkl

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

Acknowledgments

We are grateful for financial support and a grant from the ‘Qing Lan’ Talent Engineering Funds of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and the ‘Long Yuan Qing Nian’ of Gansu Province is also acknowledged.

supplementary crystallographic information

Comment

The benzimidazole core is of a wide interest because of its diverse biological activities, and it is a well known structure in medicinal chemistry (Horton et al., 2003). We are interested in tris(2-benzimidazolylmethyl)amine and its derivatives and previously reported the crystal structure of some related complexes (Wu et al., 2009; Wu et al., 2005).

The asymmetric unit of the title compound consists of a discrete [Mn(Mentb)(2-methacrylato)(DMF)] cations, a perchlorate anions, and one molecule of DMF (Fig. 1). The Mentb ligand forms a tripodal pyramidal geometry with the manganese ion, and the remaining open axial site of the complex is occupied by a chelating 2-methacrylate anion and a monodentate DMF. The complex has a seven-coordinate manganese(II) geometry with a N4O3 donor set.

Experimental

To a stirred solution of Mentb (0.5 mmol) in hot methanol (20 ml) was added Mn(ClO4)2.6 H2O (0.5 mmol) followed by a solution of Na(2-methacrylate) (0.5 mmol) in methanol (5 ml), whereupon a colorless microcrystalline precipitate was produced and collected by filtration. After drying in air the colorless product was redissolved in DMF/methanol (1:1) and filtered. Light-yellow block-shaped crystals suitable for X-ray diffraction studies were obtained by vapor diffusion of diethyl ether into the filtrate for 4 weeks at room temperature (yield 0.34 g, 82%). Elemental analysis found: C 53.21, H 5.55, N 15.09%; calcd. for C37H46N9O8MnCl: C 53.04, H 5.39, N 15.13%.

Refinement

H atoms bonded to C atoms were placed in calculated positions and included in a riding-model approximation, with C—H distances ranging from 0.93 to 0.97 Å and Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl). The coordinated DMF molecule and the perchlorate anion are disordered over two positions with occupancy factors in the ratio 16/9. In the refinement, several constrains were applied: EADP for atoms C29 C30 C31 and for atoms N8 C33 C34 C33' C34', SADI for atoms N8 C33 C34 C33' C34', DELU for atoms MN1 O2.

Figures

Fig. 1.
Molecular structure and atom numbering of the title compound with displacement ellipsoides drawn at the 30% probability level. H atoms bonded to C atoms have been omitted for clarity.

Crystal data

[Mn(C4H5O2)(C27H27N7)(C3H7NO)]ClO4·C3H7NOZ = 2
Mr = 835.22F(000) = 874
Triclinic, P1Dx = 1.328 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.139 (5) ÅCell parameters from 6078 reflections
b = 12.354 (5) Åθ = 2.3–26.9°
c = 15.146 (6) ŵ = 0.44 mm1
α = 89.168 (4)°T = 296 K
β = 71.098 (4)°Block, light-yellow
γ = 76.936 (5)°0.38 × 0.34 × 0.30 mm
V = 2088.9 (14) Å3

Data collection

Bruker APEXII area-detector diffractometer7680 independent reflections
Radiation source: fine-focus sealed tube5422 reflections with I > 2σ(I)
graphiteRint = 0.033
ω scansθmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS: Bruker, 2006)h = −14→14
Tmin = 0.851, Tmax = 0.880k = −14→13
15471 measured reflectionsl = −18→18

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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.1111P)2 + 0.1787P] where P = (Fo2 + 2Fc2)/3
7680 reflections(Δ/σ)max = 0.001
525 parametersΔρmax = 0.90 e Å3
8 restraintsΔρmin = −0.54 e Å3

Special details

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*/UeqOcc. (<1)
Mn10.78941 (4)0.30677 (4)0.72233 (3)0.04338 (18)
Cl0.42500 (11)0.73755 (8)0.62722 (8)0.0706 (3)
O10.9336 (2)0.3582 (2)0.76647 (19)0.0655 (7)
O20.8252 (3)0.2580 (2)0.86003 (18)0.0720 (8)
O30.9336 (3)0.1338 (2)0.6630 (2)0.0757 (8)
O40.4724 (4)0.7215 (3)0.7008 (3)0.1208 (14)
O50.3586 (10)0.6632 (8)0.6261 (7)0.101 (3)0.640 (8)
O5'0.3062 (18)0.740 (4)0.669 (2)0.262 (15)0.360 (8)
O60.5290 (5)0.7232 (11)0.5421 (4)0.111 (3)0.640 (8)
O6'0.463 (3)0.6437 (14)0.5688 (19)0.190 (13)0.360 (8)
O70.3568 (13)0.8430 (9)0.6244 (10)0.131 (5)0.640 (8)
O7'0.423 (3)0.8347 (19)0.5935 (19)0.172 (16)0.360 (8)
O80.3489 (4)0.2371 (5)0.7818 (4)0.1465 (19)
N10.6526 (2)0.4681 (2)0.79600 (18)0.0437 (6)
N20.4589 (2)0.5539 (2)0.85885 (19)0.0494 (7)
N30.6674 (3)0.1841 (2)0.74261 (18)0.0477 (6)
N40.6038 (3)0.0753 (2)0.66356 (19)0.0524 (7)
N50.8692 (2)0.3485 (2)0.57493 (18)0.0473 (6)
N60.8642 (3)0.4395 (2)0.4480 (2)0.0581 (8)
N70.6286 (2)0.3665 (2)0.64674 (18)0.0451 (6)
N81.0068 (5)−0.0478 (4)0.6781 (4)0.1245 (16)
N90.2678 (5)0.0927 (5)0.7980 (4)0.131 (2)
C10.5169 (3)0.4191 (3)0.7206 (2)0.0513 (8)
H1A0.47580.36250.75010.062*
H1B0.46490.46980.69350.062*
C20.5432 (3)0.4806 (3)0.7911 (2)0.0448 (7)
C30.3310 (3)0.5872 (4)0.8722 (3)0.0681 (10)
H3A0.31580.65010.83620.102*
H3B0.28710.60710.93720.102*
H3C0.30590.52650.85190.102*
C40.5162 (3)0.5930 (3)0.9121 (2)0.0478 (8)
C50.4734 (4)0.6652 (3)0.9913 (2)0.0601 (10)
H50.39210.69751.01840.072*
C60.5565 (4)0.6868 (3)1.0279 (2)0.0631 (10)
H60.53090.73471.08120.076*
C70.6773 (4)0.6392 (3)0.9874 (3)0.0639 (10)
H70.73130.65731.01320.077*
C80.7203 (3)0.5645 (3)0.9086 (2)0.0538 (8)
H80.80170.53230.88190.065*
C90.6373 (3)0.5401 (3)0.8718 (2)0.0438 (7)
C100.6214 (3)0.2630 (3)0.6052 (2)0.0517 (8)
H10A0.68550.24270.54590.062*
H10B0.54560.27330.59390.062*
C110.6318 (3)0.1731 (3)0.6710 (2)0.0454 (7)
C120.5611 (4)0.0362 (3)0.5929 (3)0.0752 (12)
H12A0.52150.09910.56770.113*
H12B0.5060−0.00920.62090.113*
H12C0.6279−0.00680.54360.113*
C130.6210 (3)0.0157 (3)0.7386 (2)0.0541 (8)
C140.6035 (4)−0.0882 (3)0.7658 (3)0.0721 (11)
H140.5785−0.13350.73140.086*
C150.6253 (5)−0.1200 (4)0.8462 (3)0.0934 (16)
H150.6138−0.18880.86780.112*
C160.6642 (5)−0.0528 (4)0.8971 (3)0.0887 (15)
H160.6786−0.07840.95130.106*
C170.6822 (4)0.0506 (3)0.8695 (3)0.0672 (11)
H170.70770.09540.90400.081*
C180.6601 (3)0.0845 (3)0.7875 (2)0.0523 (8)
C190.6679 (3)0.4447 (3)0.5758 (2)0.0509 (8)
H19A0.64450.51970.60450.061*
H19B0.63060.44400.52810.061*
C200.8004 (3)0.4101 (3)0.5331 (2)0.0479 (8)
C210.8145 (5)0.5073 (4)0.3826 (3)0.0786 (13)
H21A0.86890.55140.34970.118*
H21B0.73880.55540.41690.118*
H21C0.80360.45910.33850.118*
C220.9825 (4)0.3943 (3)0.4344 (2)0.0570 (9)
C231.0863 (5)0.3980 (4)0.3602 (3)0.0747 (12)
H231.08330.43730.30790.090*
C241.1928 (5)0.3405 (4)0.3687 (3)0.0857 (14)
H241.26360.34020.32050.103*
C251.1982 (4)0.2829 (4)0.4467 (3)0.0795 (12)
H251.27240.24540.44990.095*
C261.0948 (4)0.2799 (3)0.5206 (3)0.0679 (10)
H261.09850.24080.57300.081*
C270.9862 (3)0.3374 (3)0.5132 (2)0.0517 (8)
C280.9084 (3)0.3102 (3)0.8409 (3)0.0598 (10)
C290.9747 (6)0.3139 (7)0.9058 (4)0.1252 (15)
C311.0517 (5)0.3945 (6)0.8873 (4)0.1252 (15)
H31A1.08360.39650.93740.188*
H31B1.00510.46710.88300.188*
H31C1.11620.37210.82950.188*
C300.9638 (5)0.2499 (6)0.9765 (4)0.1252 (15)
H30A0.91340.20110.98600.150*
H30B1.00650.25321.01710.150*
C320.9487 (4)0.0529 (4)0.7078 (4)0.0821 (13)
H320.91370.06520.77230.099*
C331.0101 (11)−0.1517 (6)0.7264 (8)0.1245 (16)0.640 (8)
H33A0.9790−0.13470.79280.187*0.640 (8)
H33B1.0913−0.19450.70940.187*0.640 (8)
H33C0.9623−0.19380.70870.187*0.640 (8)
C33'1.0174 (19)−0.1210 (11)0.7540 (9)0.1245 (16)0.360 (8)
H33D1.0376−0.08260.79920.187*0.360 (8)
H33E1.0790−0.18720.72870.187*0.360 (8)
H33F0.9425−0.14090.78380.187*0.360 (8)
C341.0828 (9)−0.0635 (7)0.5788 (6)0.1245 (16)0.640 (8)
H34A1.0330−0.04830.54000.187*0.640 (8)
H34B1.1294−0.13890.56550.187*0.640 (8)
H34C1.1353−0.01350.56640.187*0.640 (8)
C34'1.0205 (19)−0.1070 (12)0.5909 (9)0.1245 (16)0.360 (8)
H34D0.9432−0.10060.58450.187*0.360 (8)
H34E1.0577−0.18410.59190.187*0.360 (8)
H34F1.0697−0.07510.53900.187*0.360 (8)
C350.3276 (6)0.1548 (7)0.8206 (5)0.122 (2)
H350.35620.13500.87010.146*
C360.2514 (11)−0.0045 (10)0.8492 (8)0.230 (6)
H36A0.3055−0.01970.88460.345*
H36B0.2674−0.06700.80630.345*
H36C0.17040.00830.89100.345*
C370.2181 (7)0.1126 (8)0.7233 (7)0.190 (5)
H37A0.13230.13070.74890.286*
H37B0.24470.04700.68180.286*
H37C0.24420.17350.68940.286*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.0455 (3)0.0413 (3)0.0407 (3)−0.0102 (2)−0.0107 (2)0.0032 (2)
Cl0.0939 (8)0.0588 (6)0.0796 (7)−0.0275 (6)−0.0500 (7)0.0179 (5)
O10.0589 (16)0.0718 (18)0.0626 (16)−0.0108 (14)−0.0186 (14)−0.0053 (14)
O20.0749 (19)0.0780 (19)0.0576 (14)−0.0080 (16)−0.0216 (14)0.0110 (13)
O30.0718 (19)0.0590 (18)0.085 (2)−0.0056 (14)−0.0164 (16)0.0000 (15)
O40.178 (4)0.139 (3)0.104 (3)−0.088 (3)−0.092 (3)0.047 (2)
O50.133 (7)0.091 (6)0.129 (6)−0.078 (5)−0.076 (6)0.039 (5)
O5'0.100 (13)0.31 (4)0.31 (3)0.021 (18)−0.026 (16)0.07 (3)
O60.066 (4)0.176 (9)0.081 (4)−0.014 (4)−0.020 (3)0.017 (5)
O6'0.31 (3)0.089 (11)0.21 (2)0.070 (15)−0.21 (2)−0.072 (13)
O70.165 (9)0.061 (6)0.132 (8)0.018 (7)−0.033 (7)0.007 (5)
O7'0.36 (4)0.11 (2)0.15 (2)−0.15 (3)−0.17 (3)0.093 (17)
O80.106 (3)0.148 (5)0.172 (5)−0.058 (3)−0.007 (3)−0.030 (4)
N10.0414 (15)0.0390 (14)0.0439 (14)−0.0062 (12)−0.0071 (12)0.0013 (11)
N20.0401 (15)0.0471 (16)0.0472 (15)−0.0060 (13)0.0012 (13)0.0081 (13)
N30.0549 (17)0.0387 (15)0.0468 (15)−0.0130 (13)−0.0122 (14)0.0066 (12)
N40.0658 (19)0.0438 (16)0.0499 (16)−0.0199 (14)−0.0172 (15)0.0031 (13)
N50.0503 (16)0.0414 (15)0.0434 (14)−0.0120 (13)−0.0053 (13)0.0017 (12)
N60.077 (2)0.0525 (18)0.0455 (16)−0.0262 (16)−0.0139 (16)0.0113 (13)
N70.0509 (16)0.0371 (14)0.0464 (15)−0.0133 (12)−0.0131 (13)0.0079 (11)
N80.130 (3)0.060 (2)0.192 (4)0.000 (2)−0.078 (3)−0.022 (3)
N90.098 (4)0.134 (5)0.145 (5)−0.048 (3)−0.003 (3)−0.058 (4)
C10.0450 (19)0.047 (2)0.061 (2)−0.0115 (15)−0.0166 (17)0.0082 (16)
C20.0453 (19)0.0389 (17)0.0443 (17)−0.0098 (14)−0.0073 (15)0.0099 (14)
C30.044 (2)0.071 (3)0.072 (3)−0.0028 (19)−0.0036 (19)0.010 (2)
C40.055 (2)0.0366 (17)0.0406 (17)−0.0086 (15)−0.0026 (16)0.0096 (14)
C50.070 (3)0.044 (2)0.0439 (19)−0.0052 (18)0.0059 (19)0.0069 (15)
C60.091 (3)0.045 (2)0.0378 (18)−0.007 (2)−0.007 (2)−0.0021 (15)
C70.084 (3)0.056 (2)0.052 (2)−0.014 (2)−0.024 (2)0.0008 (17)
C80.056 (2)0.050 (2)0.0482 (19)−0.0062 (16)−0.0115 (17)0.0012 (16)
C90.0522 (19)0.0360 (17)0.0358 (16)−0.0097 (14)−0.0048 (15)0.0055 (13)
C100.067 (2)0.0474 (19)0.0470 (18)−0.0198 (17)−0.0222 (18)0.0062 (15)
C110.0483 (19)0.0400 (17)0.0454 (17)−0.0137 (15)−0.0096 (15)0.0022 (14)
C120.107 (4)0.060 (2)0.071 (3)−0.037 (2)−0.033 (3)0.000 (2)
C130.062 (2)0.0429 (19)0.0512 (19)−0.0149 (17)−0.0080 (18)0.0042 (15)
C140.093 (3)0.047 (2)0.073 (3)−0.028 (2)−0.016 (2)0.0063 (19)
C150.147 (5)0.055 (3)0.078 (3)−0.039 (3)−0.027 (3)0.026 (2)
C160.139 (5)0.066 (3)0.060 (3)−0.030 (3)−0.027 (3)0.026 (2)
C170.091 (3)0.055 (2)0.055 (2)−0.018 (2)−0.022 (2)0.0100 (18)
C180.055 (2)0.0433 (19)0.0521 (19)−0.0105 (16)−0.0105 (17)0.0093 (15)
C190.066 (2)0.0404 (18)0.0482 (18)−0.0148 (16)−0.0204 (18)0.0109 (14)
C200.063 (2)0.0402 (18)0.0401 (17)−0.0207 (16)−0.0112 (17)0.0035 (14)
C210.108 (4)0.079 (3)0.059 (2)−0.043 (3)−0.028 (2)0.032 (2)
C220.073 (3)0.0433 (19)0.0475 (19)−0.0252 (18)−0.0015 (19)−0.0051 (15)
C230.093 (3)0.065 (3)0.055 (2)−0.040 (3)0.005 (2)−0.0015 (19)
C240.082 (3)0.072 (3)0.081 (3)−0.040 (3)0.019 (3)−0.010 (2)
C250.058 (3)0.071 (3)0.093 (3)−0.019 (2)0.001 (2)−0.009 (3)
C260.061 (3)0.059 (2)0.073 (3)−0.015 (2)−0.007 (2)−0.006 (2)
C270.056 (2)0.0402 (18)0.0497 (19)−0.0172 (16)−0.0013 (17)−0.0059 (15)
C280.048 (2)0.064 (2)0.059 (2)0.0026 (19)−0.0163 (19)−0.0164 (19)
C290.091 (2)0.182 (4)0.095 (2)0.011 (2)−0.048 (2)−0.026 (2)
C310.091 (2)0.182 (4)0.095 (2)0.011 (2)−0.048 (2)−0.026 (2)
C300.091 (2)0.182 (4)0.095 (2)0.011 (2)−0.048 (2)−0.026 (2)
C320.067 (3)0.054 (3)0.113 (4)−0.011 (2)−0.015 (3)0.001 (3)
C330.130 (3)0.060 (2)0.192 (4)0.000 (2)−0.078 (3)−0.022 (3)
C33'0.130 (3)0.060 (2)0.192 (4)0.000 (2)−0.078 (3)−0.022 (3)
C340.130 (3)0.060 (2)0.192 (4)0.000 (2)−0.078 (3)−0.022 (3)
C34'0.130 (3)0.060 (2)0.192 (4)0.000 (2)−0.078 (3)−0.022 (3)
C350.098 (5)0.147 (7)0.112 (5)−0.042 (5)−0.010 (4)−0.047 (5)
C360.237 (13)0.191 (11)0.210 (11)−0.105 (10)0.035 (9)−0.064 (9)
C370.131 (6)0.195 (9)0.251 (10)0.021 (6)−0.106 (7)−0.111 (8)

Geometric parameters (Å, °)

Mn1—N52.231 (3)C10—C111.493 (4)
Mn1—O12.278 (3)C10—H10A0.9700
Mn1—N32.301 (3)C10—H10B0.9700
Mn1—O22.310 (3)C12—H12A0.9600
Mn1—N12.311 (3)C12—H12B0.9600
Mn1—O32.405 (3)C12—H12C0.9600
Mn1—N72.538 (3)C13—C141.384 (5)
Cl—O7'1.30 (2)C13—C181.388 (5)
Cl—O51.356 (5)C14—C151.362 (6)
Cl—O6'1.365 (12)C14—H140.9300
Cl—O5'1.37 (2)C15—C161.392 (7)
Cl—O71.385 (11)C15—H150.9300
Cl—O41.403 (3)C16—C171.380 (6)
Cl—O61.462 (6)C16—H160.9300
O1—C281.248 (5)C17—C181.393 (5)
O2—C281.272 (5)C17—H170.9300
O3—C321.212 (5)C19—C201.487 (5)
O8—C351.203 (9)C19—H19A0.9700
N1—C21.328 (4)C19—H19B0.9700
N1—C91.401 (4)C21—H21A0.9600
N2—C21.359 (4)C21—H21B0.9600
N2—C41.377 (4)C21—H21C0.9600
N2—C31.460 (4)C22—C271.386 (5)
N3—C111.310 (4)C22—C231.400 (6)
N3—C181.403 (4)C23—C241.373 (7)
N4—C111.343 (4)C23—H230.9300
N4—C131.391 (4)C24—C251.382 (7)
N4—C121.461 (4)C24—H240.9300
N5—C201.312 (4)C25—C261.393 (6)
N5—C271.401 (4)C25—H250.9300
N6—C201.364 (4)C26—C271.388 (5)
N6—C221.365 (5)C26—H260.9300
N6—C211.477 (5)C28—C291.464 (6)
N7—C101.465 (4)C29—C301.312 (10)
N7—C11.466 (4)C29—C311.478 (10)
N7—C191.471 (4)C31—H31A0.9600
N8—C321.289 (6)C31—H31B0.9600
N8—C34'1.462 (7)C31—H31C0.9600
N8—C331.467 (6)C30—H30A0.9300
N8—C33'1.473 (7)C30—H30B0.9300
N8—C341.476 (7)C32—H320.9300
N9—C351.286 (7)C33—H33A0.9600
N9—C361.437 (12)C33—H33B0.9600
N9—C371.439 (10)C33—H33C0.9600
C1—C21.475 (5)C33'—H33D0.9600
C1—H1A0.9700C33'—H33E0.9600
C1—H1B0.9700C33'—H33F0.9600
C3—H3A0.9600C34—H34A0.9600
C3—H3B0.9600C34—H34B0.9600
C3—H3C0.9600C34—H34C0.9600
C4—C51.387 (5)C34'—H34D0.9600
C4—C91.399 (5)C34'—H34E0.9600
C5—C61.373 (6)C34'—H34F0.9600
C5—H50.9300C35—H350.9300
C6—C71.382 (6)C36—H36A0.9600
C6—H60.9300C36—H36B0.9600
C7—C81.400 (5)C36—H36C0.9600
C7—H70.9300C37—H37A0.9600
C8—C91.387 (5)C37—H37B0.9600
C8—H80.9300C37—H37C0.9600
N5—Mn1—O192.23 (10)N4—C11—C10123.6 (3)
N5—Mn1—N3115.22 (10)N4—C12—H12A109.5
O1—Mn1—N3145.55 (10)N4—C12—H12B109.5
N5—Mn1—O2145.57 (11)H12A—C12—H12B109.5
O1—Mn1—O256.72 (11)N4—C12—H12C109.5
N3—Mn1—O290.47 (10)H12A—C12—H12C109.5
N5—Mn1—N1105.01 (10)H12B—C12—H12C109.5
O1—Mn1—N190.47 (10)C14—C13—C18123.6 (3)
N3—Mn1—N1101.20 (10)C14—C13—N4131.2 (3)
O2—Mn1—N190.95 (10)C18—C13—N4105.3 (3)
N5—Mn1—O380.88 (11)C15—C14—C13115.8 (4)
O1—Mn1—O386.30 (10)C15—C14—H14122.1
N3—Mn1—O378.50 (10)C13—C14—H14122.1
O2—Mn1—O382.48 (11)C14—C15—C16122.1 (4)
N1—Mn1—O3173.41 (9)C14—C15—H15119.0
N5—Mn1—N769.34 (10)C16—C15—H15119.0
O1—Mn1—N7145.78 (10)C17—C16—C15122.0 (4)
N3—Mn1—N767.56 (9)C17—C16—H16119.0
O2—Mn1—N7144.83 (10)C15—C16—H16119.0
N1—Mn1—N768.32 (9)C16—C17—C18116.7 (4)
O3—Mn1—N7117.15 (10)C16—C17—H17121.7
O7'—Cl—O6'120.4 (15)C18—C17—H17121.7
O7'—Cl—O5'102.9 (18)C13—C18—C17119.9 (3)
O6'—Cl—O5'101.4 (18)C13—C18—N3109.6 (3)
O5—Cl—O7107.9 (8)C17—C18—N3130.5 (3)
O7'—Cl—O4114.3 (9)N7—C19—C20108.4 (3)
O5—Cl—O4111.4 (3)N7—C19—H19A110.0
O6'—Cl—O4110.8 (5)C20—C19—H19A110.0
O5'—Cl—O4104.3 (13)N7—C19—H19B110.0
O7—Cl—O4116.3 (7)C20—C19—H19B110.0
O5—Cl—O6111.2 (5)H19A—C19—H19B108.4
O7—Cl—O6104.7 (6)N5—C20—N6112.4 (3)
O4—Cl—O6105.2 (3)N5—C20—C19123.0 (3)
C28—O1—Mn192.8 (2)N6—C20—C19124.6 (3)
C28—O2—Mn190.7 (2)N6—C21—H21A109.5
C32—O3—Mn1125.4 (3)N6—C21—H21B109.5
C2—N1—C9104.4 (3)H21A—C21—H21B109.5
C2—N1—Mn1115.8 (2)N6—C21—H21C109.5
C9—N1—Mn1135.5 (2)H21A—C21—H21C109.5
C2—N2—C4107.6 (3)H21B—C21—H21C109.5
C2—N2—C3126.6 (3)N6—C22—C27106.0 (3)
C4—N2—C3125.8 (3)N6—C22—C23131.8 (4)
C11—N3—C18104.4 (3)C27—C22—C23122.2 (4)
C11—N3—Mn1113.6 (2)C24—C23—C22116.5 (4)
C18—N3—Mn1135.2 (2)C24—C23—H23121.7
C11—N4—C13106.8 (3)C22—C23—H23121.7
C11—N4—C12128.2 (3)C23—C24—C25122.1 (4)
C13—N4—C12125.0 (3)C23—C24—H24118.9
C20—N5—C27105.0 (3)C25—C24—H24118.9
C20—N5—Mn1119.5 (2)C24—C25—C26121.3 (5)
C27—N5—Mn1134.8 (2)C24—C25—H25119.4
C20—N6—C22107.3 (3)C26—C25—H25119.4
C20—N6—C21126.3 (3)C27—C26—C25117.5 (4)
C22—N6—C21126.4 (3)C27—C26—H26121.3
C10—N7—C1112.4 (3)C25—C26—H26121.3
C10—N7—C19112.2 (2)C22—C27—C26120.4 (4)
C1—N7—C19111.6 (3)C22—C27—N5109.2 (3)
C10—N7—Mn1104.70 (18)C26—C27—N5130.3 (3)
C1—N7—Mn1107.67 (18)O1—C28—O2119.7 (3)
C19—N7—Mn1107.78 (19)O1—C28—C29119.9 (5)
C32—N8—C34'128.0 (7)O2—C28—C29120.3 (5)
C32—N8—C33130.8 (7)C30—C29—C28121.0 (7)
C32—N8—C33'113.2 (8)C30—C29—C31122.9 (5)
C34'—N8—C33'114.1 (7)C28—C29—C31116.1 (6)
C32—N8—C34115.8 (6)C29—C31—H31A109.5
C33—N8—C34113.4 (6)C29—C31—H31B109.5
C35—N9—C36118.1 (9)H31A—C31—H31B109.5
C35—N9—C37124.4 (8)C29—C31—H31C109.5
C36—N9—C37117.6 (7)H31A—C31—H31C109.5
N7—C1—C2110.0 (3)H31B—C31—H31C109.5
N7—C1—H1A109.7C29—C30—H30A120.0
C2—C1—H1A109.7C29—C30—H30B120.0
N7—C1—H1B109.7H30A—C30—H30B120.0
C2—C1—H1B109.7O3—C32—N8128.8 (6)
H1A—C1—H1B108.2O3—C32—H32115.6
N1—C2—N2112.8 (3)N8—C32—H32115.6
N1—C2—C1123.1 (3)N8—C33—H33A109.5
N2—C2—C1124.1 (3)N8—C33—H33B109.5
N2—C3—H3A109.5N8—C33—H33C109.5
N2—C3—H3B109.5N8—C33'—H33D109.5
H3A—C3—H3B109.5N8—C33'—H33E109.5
N2—C3—H3C109.5H33D—C33'—H33E109.5
H3A—C3—H3C109.5N8—C33'—H33F109.5
H3B—C3—H3C109.5H33D—C33'—H33F109.5
N2—C4—C5131.9 (3)H33E—C33'—H33F109.5
N2—C4—C9105.3 (3)N8—C34—H34A109.5
C5—C4—C9122.8 (3)N8—C34—H34B109.5
C6—C5—C4116.9 (4)N8—C34—H34C109.5
C6—C5—H5121.6N8—C34'—H34D109.5
C4—C5—H5121.6N8—C34'—H34E109.5
C5—C6—C7121.6 (3)H34D—C34'—H34E109.5
C5—C6—H6119.2N8—C34'—H34F109.5
C7—C6—H6119.2H34D—C34'—H34F109.5
C6—C7—C8121.6 (4)H34E—C34'—H34F109.5
C6—C7—H7119.2O8—C35—N9124.0 (8)
C8—C7—H7119.2O8—C35—H35118.0
C9—C8—C7117.6 (4)N9—C35—H35118.0
C9—C8—H8121.2N9—C36—H36A109.5
C7—C8—H8121.2N9—C36—H36B109.5
C8—C9—C4119.5 (3)H36A—C36—H36B109.5
C8—C9—N1130.6 (3)N9—C36—H36C109.5
C4—C9—N1109.9 (3)H36A—C36—H36C109.5
N7—C10—C11108.8 (2)H36B—C36—H36C109.5
N7—C10—H10A109.9N9—C37—H37A109.5
C11—C10—H10A109.9N9—C37—H37B109.5
N7—C10—H10B109.9H37A—C37—H37B109.5
C11—C10—H10B109.9N9—C37—H37C109.5
H10A—C10—H10B108.3H37A—C37—H37C109.5
N3—C11—N4114.0 (3)H37B—C37—H37C109.5
N3—C11—C10122.5 (3)
N5—Mn1—O1—C28−164.5 (2)C5—C6—C7—C8−1.7 (6)
N3—Mn1—O1—C28−20.3 (3)C6—C7—C8—C90.4 (5)
O2—Mn1—O1—C28−0.4 (2)C7—C8—C9—C42.1 (5)
N1—Mn1—O1—C2890.5 (2)C7—C8—C9—N1−178.5 (3)
O3—Mn1—O1—C28−83.8 (2)N2—C4—C9—C8178.4 (3)
N7—Mn1—O1—C28140.3 (2)C5—C4—C9—C8−3.6 (5)
N5—Mn1—O2—C2829.2 (3)N2—C4—C9—N1−1.1 (3)
O1—Mn1—O2—C280.3 (2)C5—C4—C9—N1176.9 (3)
N3—Mn1—O2—C28169.2 (2)C2—N1—C9—C8−178.1 (3)
N1—Mn1—O2—C28−89.6 (2)Mn1—N1—C9—C827.5 (5)
O3—Mn1—O2—C2890.9 (2)C2—N1—C9—C41.2 (3)
N7—Mn1—O2—C28−141.4 (2)Mn1—N1—C9—C4−153.1 (2)
N5—Mn1—O3—C32−179.4 (4)C1—N7—C10—C11−76.5 (3)
O1—Mn1—O3—C3287.7 (4)C19—N7—C10—C11156.7 (3)
N3—Mn1—O3—C32−61.2 (4)Mn1—N7—C10—C1140.1 (3)
O2—Mn1—O3—C3230.8 (4)C18—N3—C11—N4−1.1 (4)
N1—Mn1—O3—C3226.9 (10)Mn1—N3—C11—N4154.6 (2)
N7—Mn1—O3—C32−118.4 (4)C18—N3—C11—C10177.7 (3)
N5—Mn1—N1—C287.7 (2)Mn1—N3—C11—C10−26.6 (4)
O1—Mn1—N1—C2−179.9 (2)C13—N4—C11—N30.9 (4)
N3—Mn1—N1—C2−32.5 (2)C12—N4—C11—N3179.8 (4)
O2—Mn1—N1—C2−123.1 (2)C13—N4—C11—C10−177.9 (3)
O3—Mn1—N1—C2−119.3 (8)C12—N4—C11—C101.0 (6)
N7—Mn1—N1—C227.7 (2)N7—C10—C11—N3−13.2 (5)
N5—Mn1—N1—C9−120.1 (3)N7—C10—C11—N4165.5 (3)
O1—Mn1—N1—C9−27.6 (3)C11—N4—C13—C14178.6 (4)
N3—Mn1—N1—C9119.7 (3)C12—N4—C13—C14−0.3 (7)
O2—Mn1—N1—C929.1 (3)C11—N4—C13—C18−0.3 (4)
O3—Mn1—N1—C932.9 (10)C12—N4—C13—C18−179.2 (4)
N7—Mn1—N1—C9179.9 (3)C18—C13—C14—C151.1 (6)
N5—Mn1—N3—C11−16.8 (3)N4—C13—C14—C15−177.6 (4)
O1—Mn1—N3—C11−156.5 (2)C13—C14—C15—C16−0.8 (8)
O2—Mn1—N3—C11−173.1 (2)C14—C15—C16—C170.5 (9)
N1—Mn1—N3—C1195.9 (2)C15—C16—C17—C18−0.4 (8)
O3—Mn1—N3—C11−90.9 (2)C14—C13—C18—C17−1.0 (6)
N7—Mn1—N3—C1135.1 (2)N4—C13—C18—C17178.0 (4)
N5—Mn1—N3—C18128.7 (3)C14—C13—C18—N3−179.3 (4)
O1—Mn1—N3—C18−11.0 (4)N4—C13—C18—N3−0.3 (4)
O2—Mn1—N3—C18−27.6 (3)C16—C17—C18—C130.6 (6)
N1—Mn1—N3—C18−118.6 (3)C16—C17—C18—N3178.5 (4)
O3—Mn1—N3—C1854.7 (3)C11—N3—C18—C130.8 (4)
N7—Mn1—N3—C18−179.3 (3)Mn1—N3—C18—C13−146.8 (3)
O1—Mn1—N5—C20−130.9 (2)C11—N3—C18—C17−177.2 (4)
N3—Mn1—N5—C2070.5 (3)Mn1—N3—C18—C1735.2 (6)
O2—Mn1—N5—C20−154.8 (2)C10—N7—C19—C20−80.3 (3)
N1—Mn1—N5—C20−39.9 (2)C1—N7—C19—C20152.5 (3)
O3—Mn1—N5—C20143.2 (2)Mn1—N7—C19—C2034.4 (3)
N7—Mn1—N5—C2019.5 (2)C27—N5—C20—N60.4 (4)
O1—Mn1—N5—C2738.2 (3)Mn1—N5—C20—N6172.5 (2)
N3—Mn1—N5—C27−120.3 (3)C27—N5—C20—C19−178.6 (3)
O2—Mn1—N5—C2714.3 (4)Mn1—N5—C20—C19−6.6 (4)
N1—Mn1—N5—C27129.3 (3)C22—N6—C20—N5−0.5 (4)
O3—Mn1—N5—C27−47.7 (3)C21—N6—C20—N5179.3 (3)
N7—Mn1—N5—C27−171.4 (3)C22—N6—C20—C19178.5 (3)
N5—Mn1—N7—C1090.4 (2)C21—N6—C20—C19−1.7 (5)
O1—Mn1—N7—C10151.6 (2)N7—C19—C20—N5−22.2 (4)
N3—Mn1—N7—C10−40.06 (19)N7—C19—C20—N6158.9 (3)
O2—Mn1—N7—C10−95.3 (2)C20—N6—C22—C270.3 (4)
N1—Mn1—N7—C10−153.0 (2)C21—N6—C22—C27−179.4 (3)
O3—Mn1—N7—C1022.9 (2)C20—N6—C22—C23−179.8 (4)
N5—Mn1—N7—C1−149.8 (2)C21—N6—C22—C230.4 (6)
O1—Mn1—N7—C1−88.5 (2)N6—C22—C23—C24−178.8 (4)
N3—Mn1—N7—C179.8 (2)C27—C22—C23—C241.0 (6)
O2—Mn1—N7—C124.6 (3)C22—C23—C24—C25−0.8 (6)
N1—Mn1—N7—C1−33.21 (19)C23—C24—C25—C260.5 (7)
O3—Mn1—N7—C1142.76 (19)C24—C25—C26—C27−0.3 (6)
N5—Mn1—N7—C19−29.3 (2)N6—C22—C27—C26179.0 (3)
O1—Mn1—N7—C1932.0 (3)C23—C22—C27—C26−0.9 (5)
N3—Mn1—N7—C19−159.7 (2)N6—C22—C27—N5−0.1 (4)
O2—Mn1—N7—C19145.1 (2)C23—C22—C27—N5−180.0 (3)
N1—Mn1—N7—C1987.3 (2)C25—C26—C27—C220.5 (5)
O3—Mn1—N7—C19−96.7 (2)C25—C26—C27—N5179.4 (3)
C10—N7—C1—C2149.6 (3)C20—N5—C27—C22−0.2 (4)
C19—N7—C1—C2−83.3 (3)Mn1—N5—C27—C22−170.4 (2)
Mn1—N7—C1—C234.8 (3)C20—N5—C27—C26−179.1 (4)
C9—N1—C2—N2−0.9 (3)Mn1—N5—C27—C2610.7 (5)
Mn1—N1—C2—N2159.4 (2)Mn1—O1—C28—O20.6 (4)
C9—N1—C2—C1−179.6 (3)Mn1—O1—C28—C29−179.5 (4)
Mn1—N1—C2—C1−19.3 (4)Mn1—O2—C28—O1−0.6 (4)
C4—N2—C2—N10.3 (3)Mn1—O2—C28—C29179.5 (4)
C3—N2—C2—N1179.1 (3)O1—C28—C29—C30−168.8 (5)
C4—N2—C2—C1179.0 (3)O2—C28—C29—C3011.1 (8)
C3—N2—C2—C1−2.2 (5)O1—C28—C29—C3112.1 (7)
N7—C1—C2—N1−13.6 (4)O2—C28—C29—C31−168.0 (5)
N7—C1—C2—N2167.9 (3)Mn1—O3—C32—N8165.8 (4)
C2—N2—C4—C5−177.2 (3)C34'—N8—C32—O3−32.7 (14)
C3—N2—C4—C53.9 (5)C33—N8—C32—O3−167.5 (7)
C2—N2—C4—C90.5 (3)C33'—N8—C32—O3173.4 (10)
C3—N2—C4—C9−178.4 (3)C34—N8—C32—O312.1 (9)
N2—C4—C5—C6179.8 (3)C36—N9—C35—O8178.6 (8)
C9—C4—C5—C62.4 (5)C37—N9—C35—O80.0 (11)
C4—C5—C6—C70.3 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2590).

References

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