metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

[1,1′-Di­benzyl-2,2′-(2-oxa­propane-1,3-diyl)di(1H-benzimidazole)-κ3N3,O,N3′]bis­(2,4,6-tri­nitrophenolato-κO1)manganese(II)

aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: wuhuilu@163.com

(Received 9 May 2012; accepted 8 June 2012; online 16 June 2012)

In the title complex, [Mn(C6H2N3O7)2(C30H26N4O)], the MnII atom is coordinated by the tridentate bis-benzimidazole ligand and two atoms of the picrate anions, in a distorted square-pyramidal geometry (τ = 0.038). One nitro O atom of one picrate ion is disordered over two sites with occupancies of 0.54 (5) and 0.46 (5).

Related literature

For related structures, see: Addison et al. (1983[Addison, A. W., Burke, P. J., Henrick, K., Rao, T. N. & Sinn, E. (1983). Inorg. Chem. 22, 3645-3653.]); Wu et al. (2009[Wu, H., Yun, R., Wang, K., Huang, X. & Sun, Q. (2009). Acta Cryst. E65, o1014.], 2011[Wu, H., Liu, B., Kou, F., Jia, F. & Kong, J. (2011). Acta Cryst. E67, m768.]). For the computation of the τ parameter describing the distortion of a square-pyramidal geometry, see: Addison et al. (1984[Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349-1356.]).

[Scheme 1]

Experimental

Crystal data
  • [Mn(C6H2N3O7)2(C30H26N4O)]

  • Mr = 969.70

  • Orthorhombic, P b c a

  • a = 22.323 (6) Å

  • b = 10.937 (3) Å

  • c = 34.130 (9) Å

  • V = 8333 (4) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.40 mm−1

  • T = 293 K

  • 0.28 × 0.21 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.895, Tmax = 0.942

  • 54714 measured reflections

  • 10276 independent reflections

  • 5820 reflections with I > 2σ(I)

  • Rint = 0.060

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.136

  • S = 1.01

  • 10276 reflections

  • 623 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Interest in bis(2-benzimidazolyl)alkanes and their derivatives is widespread (Addison et al., 1983). We have previously reported the crystal structures of some related complexes (Wu et al., 2009, 2011), and now complete this work with a new Mn(II) complex.

The complex crystallizes in the Pbca space group and its structure is shown in Fig. 1. The Mn(II) ion is coordinated by one tridentate 1,3-bis(1-benzylbenzimidazol-2-yl)-2-oxopropane ligand and two picrate ions, in a five-coordinated distorted square-pyramidal geometry. The distortion in the coordination polyhedron (τ) from a perfect trigonal bipyramidal geometry (τ = 1) toward a regular tetragonal pyramid (τ = 0) has been calculated according to the usual method (Addison et al., 1984): τ = (β-α/60) where β and α are the largest bong angles around the metal center. In the title complex, O1, N1, O2, and N3 make up the basal plane, where the largest deviation for the four atoms is 0.384 Å, while the Mn atom is shifted by 0.585 Å from the mean plane. The apical site is occupied by O9, and τ = 0.038, since β = O9—Mn1—O1 and α = N3—Mn1—N1. One O atom is disordered over two sites (O4 and O4') in a picrate ligand, and the occupancies were refined, converging to 0.54 (5) and 0.46 (5).

Related literature top

For related structures, see: Addison et al. (1983); Wu et al. (2009, 2011). For the computation of the τ parameter describing the distortion of a square-pyramidal geometry, see: Addison et al. (1984).

Experimental top

To a stirred solution of 1,3-bis(1-benzylbenzimidazol-2-yl)-2-oxopropane (0.1832 g, 0.40 mmol) in hot MeOH (5 ml) was added Mn(II) picrate (0.1032 g, 0.20 mmol) in MeOH (5 ml). A deep yellow crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH, and dried in vacuo. The dried precipitate was dissolved in DMF, resulting in a brown solution. Brown crystals suitable for X-ray diffraction studies were obtained by ether diffusion into DMF, after several days, at room temperature.

Refinement top

All H atoms were visible in a difference electron map, but were placed in idealized positions and refined in a riding-model approximation with C—H distances ranging from 0.93 to 0.97 Å and with Uiso(H) = 1.2 Ueq(carrier C). One picrate O atom is disordered over two sites, O4 and O4', with refined occupancies of 0.54 (5) and 0.46 (5).

Structure description top

Interest in bis(2-benzimidazolyl)alkanes and their derivatives is widespread (Addison et al., 1983). We have previously reported the crystal structures of some related complexes (Wu et al., 2009, 2011), and now complete this work with a new Mn(II) complex.

The complex crystallizes in the Pbca space group and its structure is shown in Fig. 1. The Mn(II) ion is coordinated by one tridentate 1,3-bis(1-benzylbenzimidazol-2-yl)-2-oxopropane ligand and two picrate ions, in a five-coordinated distorted square-pyramidal geometry. The distortion in the coordination polyhedron (τ) from a perfect trigonal bipyramidal geometry (τ = 1) toward a regular tetragonal pyramid (τ = 0) has been calculated according to the usual method (Addison et al., 1984): τ = (β-α/60) where β and α are the largest bong angles around the metal center. In the title complex, O1, N1, O2, and N3 make up the basal plane, where the largest deviation for the four atoms is 0.384 Å, while the Mn atom is shifted by 0.585 Å from the mean plane. The apical site is occupied by O9, and τ = 0.038, since β = O9—Mn1—O1 and α = N3—Mn1—N1. One O atom is disordered over two sites (O4 and O4') in a picrate ligand, and the occupancies were refined, converging to 0.54 (5) and 0.46 (5).

For related structures, see: Addison et al. (1983); Wu et al. (2009, 2011). For the computation of the τ parameter describing the distortion of a square-pyramidal geometry, see: Addison et al. (1984).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity.
[1,1'-Dibenzyl-2,2'-(2-oxapropane-1,3-diyl)di(1H-benzimidazole)- κ3N3,O,N3']bis(2,4,6-trinitrophenolato- κO1)manganese(II) top
Crystal data top
[Mn(C6H2N3O7)2(C30H26N4O)]F(000) = 3976
Mr = 969.70Dx = 1.546 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 7261 reflections
a = 22.323 (6) Åθ = 2.4–22.5°
b = 10.937 (3) ŵ = 0.40 mm1
c = 34.130 (9) ÅT = 293 K
V = 8333 (4) Å3Block, brown
Z = 80.28 × 0.21 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
10276 independent reflections
Radiation source: fine-focus sealed tube5820 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
ω scansθmax = 28.4°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1829
Tmin = 0.895, Tmax = 0.942k = 1413
54714 measured reflectionsl = 4545
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0392P)2 + 7.9255P]
where P = (Fo2 + 2Fc2)/3
10276 reflections(Δ/σ)max = 0.002
623 parametersΔρmax = 0.53 e Å3
1 restraintΔρmin = 0.42 e Å3
0 constraints
Crystal data top
[Mn(C6H2N3O7)2(C30H26N4O)]V = 8333 (4) Å3
Mr = 969.70Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 22.323 (6) ŵ = 0.40 mm1
b = 10.937 (3) ÅT = 293 K
c = 34.130 (9) Å0.28 × 0.21 × 0.15 mm
Data collection top
Bruker APEXII CCD
diffractometer
10276 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
5820 reflections with I > 2σ(I)
Tmin = 0.895, Tmax = 0.942Rint = 0.060
54714 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0581 restraint
wR(F2) = 0.136H-atom parameters constrained
S = 1.01Δρmax = 0.53 e Å3
10276 reflectionsΔρmin = 0.42 e Å3
623 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C11.01293 (13)0.4186 (2)0.10980 (9)0.0408 (7)
H1A0.97740.37570.10090.049*
H1B1.04220.35900.11860.049*
C21.03816 (12)0.4960 (2)0.07773 (8)0.0351 (6)
C31.06411 (12)0.6554 (3)0.04428 (8)0.0366 (6)
C41.07450 (14)0.7728 (3)0.03043 (9)0.0496 (8)
H41.06690.84140.04580.059*
C51.09660 (16)0.7831 (3)0.00716 (10)0.0616 (9)
H5A1.10410.86040.01740.074*
C61.10795 (16)0.6806 (4)0.03014 (10)0.0627 (10)
H61.12260.69120.05540.075*
C71.09807 (14)0.5642 (3)0.01655 (9)0.0537 (8)
H7A1.10600.49590.03190.064*
C81.07577 (12)0.5533 (3)0.02110 (8)0.0406 (7)
C91.05903 (14)0.3255 (3)0.02976 (10)0.0501 (8)
H9A1.03310.32040.00700.060*
H9B1.04170.27470.05010.060*
C101.11975 (14)0.2738 (3)0.01894 (9)0.0473 (8)
C111.17289 (16)0.3269 (4)0.02893 (11)0.0658 (10)
H111.17280.40140.04200.079*
C121.22716 (18)0.2714 (5)0.01989 (13)0.0873 (13)
H12A1.26300.30870.02700.105*
C131.2278 (2)0.1625 (4)0.00056 (16)0.0961 (16)
H13A1.26400.12370.00470.115*
C141.1750 (2)0.1107 (4)0.01101 (15)0.0965 (16)
H141.17550.03800.02510.116*
C151.12055 (18)0.1658 (3)0.00185 (12)0.0714 (11)
H151.08480.12980.00970.086*
C160.96472 (12)0.4538 (3)0.17165 (8)0.0395 (7)
H16A0.98760.39360.18620.047*
H16B0.92820.41600.16220.047*
C170.95091 (11)0.5617 (3)0.19663 (8)0.0372 (6)
C180.93908 (12)0.7491 (3)0.21505 (8)0.0415 (7)
C190.93622 (14)0.8760 (3)0.21773 (10)0.0520 (8)
H190.94690.92570.19680.062*
C200.91687 (15)0.9248 (4)0.25268 (11)0.0640 (10)
H200.91421.00920.25520.077*
C210.90137 (16)0.8517 (4)0.28403 (11)0.0711 (11)
H210.88870.88850.30720.085*
C220.90411 (15)0.7264 (4)0.28217 (9)0.0620 (10)
H220.89390.67750.30340.074*
C230.92308 (13)0.6764 (3)0.24668 (9)0.0464 (7)
C240.91835 (14)0.4451 (3)0.25692 (10)0.0588 (9)
H24A0.92220.46380.28460.071*
H24B0.94800.38340.25050.071*
C250.85704 (15)0.3937 (3)0.24952 (9)0.0495 (8)
C260.8504 (2)0.2812 (4)0.23218 (11)0.0736 (11)
H260.88400.23610.22510.088*
C270.7934 (3)0.2347 (4)0.22523 (12)0.0909 (15)
H270.78920.15850.21350.109*
C280.7437 (2)0.2995 (5)0.23540 (12)0.0867 (13)
H280.70570.26840.23040.104*
C290.75037 (18)0.4100 (4)0.25290 (13)0.0795 (12)
H290.71660.45430.26020.095*
C300.80625 (15)0.4568 (3)0.25995 (11)0.0624 (10)
H300.80990.53280.27200.075*
C311.11670 (13)0.8675 (2)0.13666 (8)0.0393 (7)
C321.13719 (14)0.9772 (3)0.11795 (9)0.0444 (7)
C331.19481 (15)1.0064 (3)0.11096 (9)0.0530 (8)
H331.20481.07890.09830.064*
C341.23870 (14)0.9258 (3)0.12305 (9)0.0518 (8)
C351.22401 (14)0.8190 (3)0.14234 (9)0.0524 (8)
H351.25400.76600.15070.063*
C361.16454 (13)0.7910 (3)0.14919 (8)0.0426 (7)
C370.88981 (13)0.8760 (3)0.11454 (9)0.0431 (7)
C380.86812 (14)0.9924 (3)0.12730 (9)0.0470 (7)
C390.81040 (14)1.0163 (3)0.13732 (9)0.0516 (8)
H390.79941.09220.14730.062*
C400.76829 (13)0.9245 (3)0.13228 (9)0.0498 (8)
C410.78354 (14)0.8138 (3)0.11696 (9)0.0483 (8)
H410.75430.75520.11210.058*
C420.84299 (13)0.7896 (3)0.10876 (9)0.0440 (7)
Mn11.000034 (19)0.71354 (4)0.128474 (12)0.03633 (12)
N11.04023 (10)0.61681 (19)0.07995 (7)0.0350 (5)
N21.05970 (10)0.4524 (2)0.04352 (7)0.0392 (6)
N30.95682 (10)0.6748 (2)0.18400 (7)0.0382 (5)
N40.93111 (10)0.5560 (2)0.23421 (7)0.0449 (6)
N51.09112 (14)1.0645 (3)0.10549 (10)0.0596 (7)
N61.30101 (15)0.9529 (4)0.11544 (10)0.0787 (11)
N71.15152 (15)0.6789 (3)0.17020 (8)0.0570 (7)
N80.91170 (14)1.0924 (3)0.12996 (11)0.0608 (8)
N90.70641 (13)0.9454 (3)0.14359 (9)0.0637 (8)
N100.85563 (12)0.6699 (2)0.09254 (8)0.0490 (6)
O10.99855 (9)0.50068 (17)0.14027 (6)0.0494 (5)
O21.06126 (9)0.84978 (19)0.14132 (7)0.0514 (5)
O31.06283 (16)1.0451 (3)0.07692 (10)0.1071 (11)
O41.0964 (14)1.1670 (8)0.1181 (5)0.093 (5)0.54 (5)
O51.31231 (13)1.0489 (3)0.09751 (9)0.0979 (11)
O61.33851 (13)0.8803 (4)0.12623 (9)0.1113 (13)
O71.19379 (13)0.6213 (2)0.18350 (8)0.0813 (8)
O81.09936 (14)0.6462 (2)0.17412 (9)0.0867 (9)
O90.94519 (9)0.85772 (18)0.10919 (7)0.0518 (5)
O100.92558 (17)1.1310 (3)0.16102 (11)0.1215 (13)
O110.93154 (16)1.1317 (3)0.09981 (11)0.1153 (12)
O120.69430 (11)1.0404 (3)0.16102 (8)0.0762 (8)
O130.66916 (12)0.8668 (3)0.13503 (9)0.0861 (9)
O140.81472 (10)0.6130 (2)0.07709 (7)0.0633 (6)
O150.90714 (10)0.6290 (2)0.09460 (7)0.0661 (7)
O4'1.0663 (13)1.124 (3)0.1326 (9)0.108 (11)0.46 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0403 (17)0.0320 (14)0.0500 (17)0.0064 (12)0.0027 (13)0.0041 (13)
C20.0270 (14)0.0347 (15)0.0437 (16)0.0060 (11)0.0008 (12)0.0072 (12)
C30.0324 (15)0.0397 (16)0.0378 (15)0.0011 (12)0.0026 (12)0.0051 (13)
C40.057 (2)0.0441 (18)0.0478 (18)0.0051 (16)0.0038 (15)0.0020 (15)
C50.067 (2)0.059 (2)0.059 (2)0.0122 (19)0.0074 (18)0.0096 (18)
C60.058 (2)0.085 (3)0.0446 (19)0.003 (2)0.0090 (16)0.0046 (19)
C70.050 (2)0.068 (2)0.0432 (18)0.0085 (17)0.0049 (15)0.0125 (17)
C80.0331 (15)0.0480 (17)0.0407 (16)0.0056 (13)0.0007 (12)0.0055 (14)
C90.0483 (19)0.0403 (17)0.062 (2)0.0096 (14)0.0043 (16)0.0180 (15)
C100.052 (2)0.0424 (17)0.0471 (18)0.0133 (15)0.0032 (15)0.0046 (14)
C110.052 (2)0.080 (3)0.065 (2)0.021 (2)0.0081 (18)0.020 (2)
C120.051 (2)0.110 (4)0.101 (3)0.022 (2)0.000 (2)0.001 (3)
C130.077 (3)0.079 (3)0.132 (4)0.039 (3)0.039 (3)0.016 (3)
C140.105 (4)0.046 (2)0.138 (4)0.021 (2)0.059 (3)0.008 (2)
C150.074 (3)0.0424 (19)0.098 (3)0.0079 (18)0.029 (2)0.0154 (19)
C160.0313 (15)0.0396 (16)0.0475 (17)0.0050 (13)0.0015 (13)0.0079 (13)
C170.0243 (14)0.0480 (17)0.0394 (16)0.0005 (12)0.0016 (12)0.0021 (13)
C180.0289 (15)0.0544 (19)0.0411 (16)0.0018 (13)0.0023 (12)0.0070 (14)
C190.0434 (18)0.053 (2)0.060 (2)0.0032 (15)0.0005 (15)0.0146 (16)
C200.048 (2)0.077 (3)0.068 (2)0.0103 (18)0.0015 (18)0.031 (2)
C210.049 (2)0.107 (3)0.058 (2)0.006 (2)0.0021 (18)0.035 (2)
C220.045 (2)0.102 (3)0.0389 (18)0.001 (2)0.0030 (15)0.006 (2)
C230.0332 (16)0.065 (2)0.0408 (17)0.0007 (15)0.0001 (13)0.0056 (15)
C240.046 (2)0.077 (2)0.053 (2)0.0041 (18)0.0035 (15)0.0287 (18)
C250.053 (2)0.052 (2)0.0443 (18)0.0009 (16)0.0103 (15)0.0167 (15)
C260.083 (3)0.066 (3)0.071 (3)0.005 (2)0.032 (2)0.008 (2)
C270.130 (4)0.072 (3)0.071 (3)0.032 (3)0.030 (3)0.017 (2)
C280.076 (3)0.106 (4)0.078 (3)0.034 (3)0.010 (2)0.001 (3)
C290.052 (2)0.079 (3)0.108 (3)0.008 (2)0.012 (2)0.002 (3)
C300.047 (2)0.056 (2)0.083 (3)0.0024 (17)0.0089 (18)0.0014 (19)
C310.0406 (17)0.0337 (15)0.0436 (17)0.0019 (13)0.0001 (13)0.0086 (12)
C320.0467 (19)0.0385 (16)0.0480 (18)0.0031 (14)0.0001 (14)0.0064 (14)
C330.057 (2)0.0525 (19)0.050 (2)0.0179 (17)0.0062 (16)0.0060 (16)
C340.0372 (18)0.069 (2)0.0490 (19)0.0118 (16)0.0067 (14)0.0154 (17)
C350.0433 (18)0.067 (2)0.0474 (18)0.0107 (17)0.0055 (15)0.0134 (16)
C360.0463 (18)0.0404 (16)0.0411 (16)0.0011 (14)0.0021 (13)0.0039 (14)
C370.0351 (17)0.0477 (17)0.0465 (17)0.0084 (14)0.0004 (13)0.0048 (14)
C380.0456 (18)0.0411 (17)0.0542 (19)0.0049 (14)0.0028 (15)0.0031 (15)
C390.053 (2)0.0501 (19)0.052 (2)0.0165 (16)0.0019 (16)0.0025 (15)
C400.0365 (17)0.061 (2)0.0521 (19)0.0141 (15)0.0064 (14)0.0064 (16)
C410.0388 (17)0.0531 (19)0.0529 (19)0.0041 (14)0.0030 (14)0.0045 (15)
C420.0398 (17)0.0463 (17)0.0458 (17)0.0059 (14)0.0033 (13)0.0021 (14)
Mn10.0378 (2)0.02768 (19)0.0435 (2)0.00007 (19)0.0120 (2)0.00267 (18)
N10.0309 (12)0.0315 (12)0.0425 (13)0.0031 (10)0.0044 (10)0.0036 (10)
N20.0383 (14)0.0343 (13)0.0450 (14)0.0058 (11)0.0019 (11)0.0103 (11)
N30.0325 (13)0.0415 (13)0.0405 (13)0.0025 (11)0.0057 (10)0.0017 (11)
N40.0334 (13)0.0618 (17)0.0394 (14)0.0020 (12)0.0041 (11)0.0112 (12)
N50.065 (2)0.0432 (16)0.070 (2)0.0043 (15)0.0056 (17)0.0050 (15)
N60.049 (2)0.127 (3)0.060 (2)0.021 (2)0.0099 (17)0.028 (2)
N70.071 (2)0.0478 (17)0.0519 (17)0.0090 (16)0.0017 (16)0.0011 (13)
N80.062 (2)0.0446 (16)0.076 (2)0.0006 (14)0.0069 (18)0.0024 (17)
N90.0457 (18)0.080 (2)0.065 (2)0.0221 (17)0.0109 (15)0.0120 (18)
N100.0452 (16)0.0499 (16)0.0518 (16)0.0008 (13)0.0044 (13)0.0078 (13)
O10.0606 (13)0.0343 (10)0.0532 (12)0.0033 (10)0.0250 (11)0.0027 (9)
O20.0342 (11)0.0486 (13)0.0714 (15)0.0064 (10)0.0051 (10)0.0056 (11)
O30.125 (3)0.102 (2)0.094 (2)0.047 (2)0.039 (2)0.012 (2)
O40.136 (13)0.036 (4)0.107 (6)0.018 (4)0.019 (7)0.011 (4)
O50.075 (2)0.126 (3)0.093 (2)0.050 (2)0.0315 (17)0.029 (2)
O60.0403 (16)0.205 (4)0.089 (2)0.010 (2)0.0017 (15)0.016 (2)
O70.105 (2)0.0704 (17)0.0686 (17)0.0253 (16)0.0214 (16)0.0119 (14)
O80.082 (2)0.0683 (18)0.110 (2)0.0113 (16)0.0096 (17)0.0382 (16)
O90.0345 (12)0.0459 (12)0.0750 (15)0.0048 (10)0.0033 (10)0.0071 (11)
O100.147 (3)0.112 (3)0.105 (3)0.055 (2)0.009 (2)0.025 (2)
O110.126 (3)0.103 (3)0.117 (3)0.044 (2)0.014 (2)0.041 (2)
O120.0657 (17)0.090 (2)0.0732 (18)0.0367 (15)0.0155 (14)0.0007 (15)
O130.0426 (15)0.102 (2)0.114 (2)0.0076 (15)0.0197 (15)0.0045 (19)
O140.0536 (15)0.0650 (15)0.0713 (16)0.0067 (12)0.0018 (12)0.0176 (13)
O150.0456 (14)0.0638 (15)0.0888 (18)0.0143 (12)0.0026 (12)0.0323 (14)
O4'0.104 (11)0.099 (15)0.122 (13)0.047 (11)0.040 (10)0.064 (12)
Geometric parameters (Å, º) top
Mn1—O22.069 (2)C16—H16B0.9700
Mn1—O92.102 (2)C17—N31.316 (3)
Mn1—N12.160 (2)C17—N41.358 (3)
Mn1—N32.168 (2)C18—C231.387 (4)
Mn1—O12.363 (2)C18—N31.392 (3)
N5—O31.181 (4)C18—C191.393 (4)
N5—O41.206 (9)C19—C201.376 (4)
N5—O4'1.259 (18)C19—H190.9300
N6—O61.211 (5)C20—C211.380 (5)
N6—O51.241 (5)C20—H200.9300
N7—O71.222 (3)C21—C221.373 (5)
N7—O81.225 (4)C21—H210.9300
N8—O101.182 (4)C22—C231.395 (4)
N8—O111.200 (4)C22—H220.9300
N9—O121.227 (4)C23—N41.396 (4)
N9—O131.231 (4)C24—N41.467 (4)
N10—O141.224 (3)C24—C251.501 (4)
N10—O151.236 (3)C24—H24A0.9700
C1—O11.411 (3)C24—H24B0.9700
C1—C21.494 (4)C25—C261.373 (5)
C1—H1A0.9700C25—C301.374 (4)
C1—H1B0.9700C26—C271.391 (6)
C2—N11.324 (3)C26—H260.9300
C2—N21.350 (3)C27—C281.360 (6)
C3—C41.388 (4)C27—H270.9300
C3—C81.393 (4)C28—C291.356 (6)
C3—N11.394 (3)C28—H280.9300
C4—C51.379 (4)C29—C301.370 (5)
C4—H40.9300C29—H290.9300
C5—C61.391 (5)C30—H300.9300
C5—H5A0.9300C31—O21.263 (3)
C6—C71.372 (5)C31—C361.422 (4)
C6—H60.9300C31—C321.434 (4)
C7—C81.383 (4)C32—C331.347 (4)
C7—H7A0.9300C32—N51.467 (4)
C8—N21.390 (4)C33—C341.381 (5)
C9—N21.465 (3)C33—H330.9300
C9—C101.514 (4)C34—C351.381 (5)
C9—H9A0.9700C34—N61.446 (4)
C9—H9B0.9700C35—C361.382 (4)
C10—C111.364 (5)C35—H350.9300
C10—C151.378 (4)C36—N71.449 (4)
C11—C121.389 (5)C37—O91.265 (3)
C11—H110.9300C37—C421.422 (4)
C12—C131.362 (6)C37—C381.430 (4)
C12—H12A0.9300C38—C391.358 (4)
C13—C141.365 (6)C38—N81.466 (4)
C13—H13A0.9300C39—C401.386 (4)
C14—C151.393 (5)C39—H390.9300
C14—H140.9300C40—C411.362 (4)
C15—H150.9300C40—N91.452 (4)
C16—O11.407 (3)C41—C421.382 (4)
C16—C171.488 (4)C41—H410.9300
C16—H16A0.9700C42—N101.450 (4)
O1—C1—C2105.4 (2)C29—C28—C27119.2 (4)
O1—C1—H1A110.7C29—C28—H28120.4
C2—C1—H1A110.7C27—C28—H28120.4
O1—C1—H1B110.7C28—C29—C30120.7 (4)
C2—C1—H1B110.7C28—C29—H29119.7
H1A—C1—H1B108.8C30—C29—H29119.7
N1—C2—N2113.0 (3)C29—C30—C25121.2 (4)
N1—C2—C1122.5 (2)C29—C30—H30119.4
N2—C2—C1124.6 (2)C25—C30—H30119.4
C4—C3—C8121.1 (3)O2—C31—C36127.4 (3)
C4—C3—N1129.9 (3)O2—C31—C32119.8 (3)
C8—C3—N1109.0 (2)C36—C31—C32112.7 (3)
C5—C4—C3116.9 (3)C33—C32—C31125.6 (3)
C5—C4—H4121.6C33—C32—N5117.6 (3)
C3—C4—H4121.6C31—C32—N5116.8 (3)
C4—C5—C6121.6 (3)C32—C33—C34118.2 (3)
C4—C5—H5A119.2C32—C33—H33120.9
C6—C5—H5A119.2C34—C33—H33120.9
C7—C6—C5121.8 (3)C35—C34—C33120.9 (3)
C7—C6—H6119.1C35—C34—N6119.2 (4)
C5—C6—H6119.1C33—C34—N6119.9 (4)
C6—C7—C8116.9 (3)C34—C35—C36119.7 (3)
C6—C7—H7A121.6C34—C35—H35120.1
C8—C7—H7A121.6C36—C35—H35120.1
C7—C8—N2132.3 (3)C35—C36—C31122.7 (3)
C7—C8—C3121.7 (3)C35—C36—N7117.6 (3)
N2—C8—C3106.0 (2)C31—C36—N7119.7 (3)
N2—C9—C10115.0 (3)O9—C37—C42126.4 (3)
N2—C9—H9A108.5O9—C37—C38121.0 (3)
C10—C9—H9A108.5C42—C37—C38112.6 (3)
N2—C9—H9B108.5C39—C38—C37124.7 (3)
C10—C9—H9B108.5C39—C38—N8118.0 (3)
H9A—C9—H9B107.5C37—C38—N8117.3 (3)
C11—C10—C15118.8 (3)C38—C39—C40118.2 (3)
C11—C10—C9124.0 (3)C38—C39—H39120.9
C15—C10—C9117.2 (3)C40—C39—H39120.9
C10—C11—C12121.2 (4)C41—C40—C39121.4 (3)
C10—C11—H11119.4C41—C40—N9118.7 (3)
C12—C11—H11119.4C39—C40—N9119.9 (3)
C13—C12—C11119.9 (4)C40—C41—C42119.2 (3)
C13—C12—H12A120.1C40—C41—H41120.4
C11—C12—H12A120.1C42—C41—H41120.4
C12—C13—C14119.6 (4)C41—C42—C37123.4 (3)
C12—C13—H13A120.2C41—C42—N10115.9 (3)
C14—C13—H13A120.2C37—C42—N10120.6 (3)
C13—C14—C15120.6 (4)O2—Mn1—O984.88 (9)
C13—C14—H14119.7O2—Mn1—N1103.93 (8)
C15—C14—H14119.7O9—Mn1—N1111.67 (9)
C10—C15—C14119.8 (4)O2—Mn1—N3104.44 (9)
C10—C15—H15120.1O9—Mn1—N399.28 (9)
C14—C15—H15120.1N1—Mn1—N3139.39 (9)
O1—C16—C17105.0 (2)O2—Mn1—O1133.06 (8)
O1—C16—H16A110.8O9—Mn1—O1141.66 (8)
C17—C16—H16A110.8N1—Mn1—O169.75 (8)
O1—C16—H16B110.8N3—Mn1—O169.66 (8)
C17—C16—H16B110.8C2—N1—C3105.4 (2)
H16A—C16—H16B108.8C2—N1—Mn1121.20 (19)
N3—C17—N4112.7 (3)C3—N1—Mn1132.84 (18)
N3—C17—C16122.5 (2)C2—N2—C8106.7 (2)
N4—C17—C16124.9 (3)C2—N2—C9127.5 (3)
C23—C18—N3109.4 (3)C8—N2—C9125.3 (2)
C23—C18—C19120.5 (3)C17—N3—C18105.7 (2)
N3—C18—C19130.1 (3)C17—N3—Mn1120.95 (18)
C20—C19—C18117.2 (3)C18—N3—Mn1132.66 (19)
C20—C19—H19121.4C17—N4—C23106.6 (2)
C18—C19—H19121.4C17—N4—C24126.9 (3)
C19—C20—C21121.8 (4)C23—N4—C24126.4 (3)
C19—C20—H20119.1O3—N5—O4120.8 (6)
C21—C20—H20119.1O3—N5—O4'117.6 (6)
C22—C21—C20122.0 (3)O4—N5—O4'45.7 (9)
C22—C21—H21119.0O3—N5—C32119.8 (3)
C20—C21—H21119.0O4—N5—C32115.7 (10)
C21—C22—C23116.4 (4)O4'—N5—C32115.6 (12)
C21—C22—H22121.8O6—N6—O5124.3 (4)
C23—C22—H22121.8O6—N6—C34118.4 (4)
C18—C23—C22122.0 (3)O5—N6—C34117.2 (4)
C18—C23—N4105.7 (3)O7—N7—O8122.9 (3)
C22—C23—N4132.4 (3)O7—N7—C36117.7 (3)
N4—C24—C25113.4 (3)O8—N7—C36119.4 (3)
N4—C24—H24A108.9O10—N8—O11123.0 (4)
C25—C24—H24A108.9O10—N8—C38119.7 (3)
N4—C24—H24B108.9O11—N8—C38117.3 (3)
C25—C24—H24B108.9O12—N9—O13123.9 (3)
H24A—C24—H24B107.7O12—N9—C40118.1 (3)
C26—C25—C30118.2 (3)O13—N9—C40118.0 (3)
C26—C25—C24120.4 (3)O14—N10—O15122.3 (3)
C30—C25—C24121.4 (3)O14—N10—C42118.6 (3)
C25—C26—C27120.0 (4)O15—N10—C42119.1 (3)
C25—C26—H26120.0C16—O1—C1116.8 (2)
C27—C26—H26120.0C16—O1—Mn1119.74 (16)
C28—C27—C26120.8 (4)C1—O1—Mn1119.88 (16)
C28—C27—H27119.6C31—O2—Mn1136.98 (19)
C26—C27—H27119.6C37—O9—Mn1129.94 (19)
O1—C1—C2—N14.2 (4)O2—Mn1—N1—C350.9 (3)
O1—C1—C2—N2177.5 (2)O9—Mn1—N1—C339.1 (3)
C8—C3—C4—C50.2 (5)N3—Mn1—N1—C3176.0 (2)
N1—C3—C4—C5177.4 (3)O1—Mn1—N1—C3178.0 (3)
C3—C4—C5—C60.0 (5)N1—C2—N2—C81.6 (3)
C4—C5—C6—C70.4 (6)C1—C2—N2—C8176.9 (3)
C5—C6—C7—C80.5 (5)N1—C2—N2—C9173.8 (3)
C6—C7—C8—N2178.5 (3)C1—C2—N2—C94.7 (4)
C6—C7—C8—C30.3 (5)C7—C8—N2—C2177.4 (3)
C4—C3—C8—C70.0 (4)C3—C8—N2—C21.6 (3)
N1—C3—C8—C7178.0 (3)C7—C8—N2—C94.9 (5)
C4—C3—C8—N2179.1 (3)C3—C8—N2—C9174.0 (3)
N1—C3—C8—N21.1 (3)C10—C9—N2—C2124.2 (3)
N2—C9—C10—C1114.4 (5)C10—C9—N2—C864.9 (4)
N2—C9—C10—C15166.4 (3)N4—C17—N3—C180.8 (3)
C15—C10—C11—C122.6 (6)C16—C17—N3—C18179.1 (2)
C9—C10—C11—C12176.6 (4)N4—C17—N3—Mn1170.76 (17)
C10—C11—C12—C130.3 (7)C16—C17—N3—Mn19.3 (4)
C11—C12—C13—C142.3 (7)C23—C18—N3—C170.7 (3)
C12—C13—C14—C152.6 (8)C19—C18—N3—C17179.7 (3)
C11—C10—C15—C142.3 (6)C23—C18—N3—Mn1169.4 (2)
C9—C10—C15—C14176.9 (4)C19—C18—N3—Mn110.1 (5)
C13—C14—C15—C100.3 (7)O2—Mn1—N3—C17131.0 (2)
O1—C16—C17—N315.9 (4)O9—Mn1—N3—C17141.9 (2)
O1—C16—C17—N4164.2 (2)N1—Mn1—N3—C172.0 (3)
C23—C18—C19—C200.2 (5)O1—Mn1—N3—C170.0 (2)
N3—C18—C19—C20179.8 (3)O2—Mn1—N3—C1837.9 (3)
C18—C19—C20—C210.6 (5)O9—Mn1—N3—C1849.2 (3)
C19—C20—C21—C220.3 (6)N1—Mn1—N3—C18170.9 (2)
C20—C21—C22—C230.4 (5)O1—Mn1—N3—C18168.9 (3)
N3—C18—C23—C22179.2 (3)N3—C17—N4—C230.6 (3)
C19—C18—C23—C220.5 (5)C16—C17—N4—C23179.3 (3)
N3—C18—C23—N40.3 (3)N3—C17—N4—C24178.4 (3)
C19—C18—C23—N4180.0 (3)C16—C17—N4—C241.5 (4)
C21—C22—C23—C180.8 (5)C18—C23—N4—C170.1 (3)
C21—C22—C23—N4179.9 (3)C22—C23—N4—C17179.5 (3)
N4—C24—C25—C26114.8 (4)C18—C23—N4—C24178.0 (3)
N4—C24—C25—C3065.5 (4)C22—C23—N4—C242.6 (5)
C30—C25—C26—C270.7 (5)C25—C24—N4—C1783.4 (4)
C24—C25—C26—C27179.6 (3)C25—C24—N4—C2394.0 (4)
C25—C26—C27—C280.1 (6)C33—C32—N5—O3103.3 (4)
C26—C27—C28—C290.8 (7)C31—C32—N5—O376.8 (4)
C27—C28—C29—C300.7 (7)C33—C32—N5—O455.5 (16)
C28—C29—C30—C250.0 (6)C31—C32—N5—O4124.4 (16)
C26—C25—C30—C290.7 (5)C33—C32—N5—O4'107 (2)
C24—C25—C30—C29179.6 (3)C31—C32—N5—O4'73 (2)
O2—C31—C32—C33179.4 (3)C35—C34—N6—O60.2 (5)
C36—C31—C32—C332.5 (4)C33—C34—N6—O6179.7 (3)
O2—C31—C32—N50.6 (4)C35—C34—N6—O5178.9 (3)
C36—C31—C32—N5177.5 (3)C33—C34—N6—O51.0 (5)
C31—C32—C33—C340.9 (5)C35—C36—N7—O76.1 (4)
N5—C32—C33—C34179.1 (3)C31—C36—N7—O7173.6 (3)
C32—C33—C34—C351.0 (5)C35—C36—N7—O8174.3 (3)
C32—C33—C34—N6178.9 (3)C31—C36—N7—O86.0 (4)
C33—C34—C35—C361.0 (5)C39—C38—N8—O1068.6 (5)
N6—C34—C35—C36178.9 (3)C37—C38—N8—O10110.9 (4)
C34—C35—C36—C310.9 (5)C39—C38—N8—O11111.0 (4)
C34—C35—C36—N7178.9 (3)C37—C38—N8—O1169.4 (4)
O2—C31—C36—C35179.7 (3)C41—C40—N9—O12172.6 (3)
C32—C31—C36—C352.4 (4)C39—C40—N9—O127.1 (5)
O2—C31—C36—N70.6 (4)C41—C40—N9—O137.5 (5)
C32—C31—C36—N7177.3 (3)C39—C40—N9—O13172.7 (3)
O9—C37—C38—C39173.4 (3)C41—C42—N10—O1420.3 (4)
C42—C37—C38—C397.2 (5)C37—C42—N10—O14158.2 (3)
O9—C37—C38—N86.1 (4)C41—C42—N10—O15160.1 (3)
C42—C37—C38—N8173.3 (3)C37—C42—N10—O1521.5 (4)
C37—C38—C39—C404.9 (5)C17—C16—O1—C1174.1 (2)
N8—C38—C39—C40175.6 (3)C17—C16—O1—Mn115.3 (3)
C38—C39—C40—C411.3 (5)C2—C1—O1—C16169.8 (2)
C38—C39—C40—N9178.4 (3)C2—C1—O1—Mn111.0 (3)
C39—C40—C41—C424.4 (5)O2—Mn1—O1—C16100.6 (2)
N9—C40—C41—C42175.3 (3)O9—Mn1—O1—C1669.3 (2)
C40—C41—C42—C371.6 (5)N1—Mn1—O1—C16169.0 (2)
C40—C41—C42—N10180.0 (3)N3—Mn1—O1—C169.61 (19)
O9—C37—C42—C41176.8 (3)O2—Mn1—O1—C1101.3 (2)
C38—C37—C42—C413.8 (4)O9—Mn1—O1—C188.8 (2)
O9—C37—C42—N104.9 (5)N1—Mn1—O1—C110.92 (19)
C38—C37—C42—N10174.5 (3)N3—Mn1—O1—C1167.7 (2)
N2—C2—N1—C30.9 (3)C36—C31—O2—Mn155.3 (5)
C1—C2—N1—C3177.6 (2)C32—C31—O2—Mn1126.9 (3)
N2—C2—N1—Mn1173.22 (17)O9—Mn1—O2—C31135.1 (3)
C1—C2—N1—Mn15.3 (4)N1—Mn1—O2—C3124.0 (3)
C4—C3—N1—C2178.0 (3)N3—Mn1—O2—C31126.6 (3)
C8—C3—N1—C20.2 (3)O1—Mn1—O2—C3151.1 (3)
C4—C3—N1—Mn17.0 (5)C42—C37—O9—Mn148.7 (4)
C8—C3—N1—Mn1170.86 (19)C38—C37—O9—Mn1131.9 (3)
O2—Mn1—N1—C2139.3 (2)O2—Mn1—O9—C37137.0 (3)
O9—Mn1—N1—C2130.8 (2)N1—Mn1—O9—C37120.0 (3)
N3—Mn1—N1—C26.1 (3)N3—Mn1—O9—C3733.2 (3)
O1—Mn1—N1—C28.1 (2)O1—Mn1—O9—C3735.6 (3)

Experimental details

Crystal data
Chemical formula[Mn(C6H2N3O7)2(C30H26N4O)]
Mr969.70
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)22.323 (6), 10.937 (3), 34.130 (9)
V3)8333 (4)
Z8
Radiation typeMo Kα
µ (mm1)0.40
Crystal size (mm)0.28 × 0.21 × 0.15
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.895, 0.942
No. of measured, independent and
observed [I > 2σ(I)] reflections
54714, 10276, 5820
Rint0.060
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.136, 1.01
No. of reflections10276
No. of parameters623
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.42

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors acknowledge the financial support and a grant from the Qing Lan Talent Engineering Funds and Students Science Funds of Lanzhou Jiaotong University.

References

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