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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): m1058.
Published online 2010 August 4. doi:  10.1107/S1600536810030357
PMCID: PMC3008082

Aqua­[1,3-bis­(benzimidazol-2-yl)-2-oxapropane]­diethano­lmanganese(II) dipicrate ethanol disolvate

Abstract

In the title complex, [Mn(C16H14N4O)(C2H5OH)2(H2O)](C6H2N3O7)2·2C2H5OH, the MnII ion is in a distorted octa­hedral coordination environment, defined by an MnN2O4 donor set. The 1,3-bis­(benz­imid­azol-2-yl)-2-oxapropane ligand is tridentate. In the crystal structure, inter­molecular N—H(...)O and O—H(...)O hydrogen bonds link the components into a three-dimensional network. The O atoms of one of the nitro groups are disordered over two sets of sites with refined occupancies of 0.577 (11) and 0.423 (11).

Related literature

For the applications of benzimidazole and bis-benzimidazole compounds, see: Chang et al. (2008 [triangle]); Harrell et al. (2004 [triangle]); Holland & Tolman (2000 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1058-scheme1.jpg

Experimental

Crystal data

  • [Mn(C16H14N4O)(C2H6O)2(H2O)](C6H2N3O7)2·2C2H6O
  • M r = 991.75
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1058-efi1.jpg
  • a = 10.0519 (3) Å
  • b = 24.8584 (8) Å
  • c = 18.0291 (7) Å
  • β = 98.504 (1)°
  • V = 4455.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.39 mm−1
  • T = 153 K
  • 0.39 × 0.25 × 0.22 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.864, T max = 0.920
  • 32660 measured reflections
  • 7806 independent reflections
  • 4707 reflections with I > 2σ(I)
  • R int = 0.045

Refinement

  • R[F 2 > 2σ(F 2)] = 0.074
  • wR(F 2) = 0.255
  • S = 1.07
  • 7806 reflections
  • 603 parameters
  • 8 restraints
  • H-atom parameters constrained
  • Δρmax = 0.73 e Å−3
  • Δρmin = −0.97 e Å−3

Data collection: APEX2 (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [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]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030357/lh5083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030357/lh5083Isup2.hkl

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

Acknowledgments

The authors acknowledge 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

Bis-benzimidazoles are known to be strong chelating agents coordinating through both of the C=N group nitrogen atoms. In addition, as a typical multidentate ligand they have polymer-forming characteristics. In bioinorganic chemistry, they have been used extensively to help model the active sites of metalloproteins (Holland & Tolman, 2000). The benzimidazole ring system is present in clinically approved anthelmintics, antiulcers, antivirals, and antihistamines (Harrell, et al., 2004). Recently, there have been reports on benzimidazole derivatives exhibiting antitumor and antimicrobial properties and acting as thrombopoietin receptor agonists (Chang, et al., 2008).

We have attempted to prepare organic-inorganic hybrid materials with manganese salts using 1,3-bis(benzimidazol-2-yl)-2-oxapropane (OBB). Herein, we report the crystal structure of the title compound. The asymmetric unit of the title compound is shown in Fig. 1. The MnII ion is coordinated in a distorted octahedral coordination environment. The 1,3-bis(benzimidazol-2-yl)-2-oxapropane ligand acts as tridentate. In the crystal structure, intermolecular N—H···O and O—H···O hydrogen bonds link the components of the structure into a three-dimensional network (Fig. 2).

Experimental

To a stirred solution of 1,3-bis(benzimidazol-2-yl)-2-oxapropane (91.6 mg, 0.2 mmol) in hot ethanol (10 ml), Mn(C6H2N3O7)2 (102.9 mg, 0.2 mmol) in ethanol (5 ml) was added. A yellow crystalline product formed rapidly. The precipitate was filtered off, washed with ethanol and Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF to form a yellow solution into which diethylether was allowed to diffuse at room temperature. The yellow crystals suitable for X-ray diffraction studies were obtained after one week (Yield, 72%).

Refinement

All H atoms were placed in calculated positions and refined in a riding-model approximation with; C—H = 0.95-0.99 Å, N-H = 0.88Å, O-H = 0.93-0.95Å and Uiso(H) = 1.2 Ueq(C, N) or Uiso(H) = 1.5 Ueq(Cmethyl, O).

Figures

Fig. 1.
The asymmetric unit of the title compound showing 30% ellipsoids.
Fig. 2.
Part of the crystal structure of the title compound showing hydrogen bonds as dashed lines. Only the H atoms involved in hydrogen bonds are shown.

Crystal data

[Mn(C16H14N4O)(C2H6O)2(H2O)](C6H2N3O7)2·2C2H6OF(000) = 2060
Mr = 991.75Dx = 1.478 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8263 reflections
a = 10.0519 (3) Åθ = 3.2–25.5°
b = 24.8584 (8) ŵ = 0.39 mm1
c = 18.0291 (7) ÅT = 153 K
β = 98.504 (1)°Block, yellow
V = 4455.5 (3) Å30.39 × 0.25 × 0.22 mm
Z = 4

Data collection

Bruker SMART APEXII diffractometer7806 independent reflections
Radiation source: fine-focus sealed tube4707 reflections with I > 2σ(I)
graphiteRint = 0.045
ω scansθmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.864, Tmax = 0.920k = −26→29
32660 measured reflectionsl = −21→21

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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.255H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.1644P)2] where P = (Fo2 + 2Fc2)/3
7806 reflections(Δ/σ)max = 0.003
603 parametersΔρmax = 0.73 e Å3
8 restraintsΔρmin = −0.97 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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)
Mn0.28926 (6)0.50170 (2)0.15226 (4)0.0402 (3)
O10.4637 (3)0.50371 (10)0.09714 (18)0.0451 (7)
H1W0.49670.53640.08260.068*
H2W0.50720.47150.09000.068*
O20.3980 (4)0.50978 (15)0.2620 (2)0.0687 (10)
H20.34590.50850.30180.082*
O30.1054 (4)0.49324 (12)0.2034 (2)0.0597 (9)
H30.06060.45960.19560.072*
O40.1588 (3)0.49524 (10)0.03089 (16)0.0380 (7)
N10.2345 (3)0.58284 (14)0.10970 (19)0.0407 (8)
N20.1547 (3)0.64007 (13)0.01947 (19)0.0401 (8)
H2B0.11840.6519−0.02490.048*
N30.2699 (3)0.41580 (13)0.11969 (19)0.0387 (8)
N40.2055 (3)0.35199 (13)0.03689 (19)0.0406 (8)
H4B0.17030.3367−0.00550.049*
C10.2462 (4)0.63501 (17)0.1386 (2)0.0410 (10)
C20.2999 (4)0.65352 (19)0.2102 (3)0.0485 (11)
H2A0.33190.62940.24970.058*
C30.3040 (5)0.70810 (19)0.2202 (3)0.0517 (12)
H3A0.34240.72200.26770.062*
C40.2539 (5)0.74418 (19)0.1633 (3)0.0516 (12)
H4A0.25830.78170.17330.062*
C50.1986 (4)0.72665 (17)0.0935 (3)0.0467 (11)
H5A0.16370.75100.05490.056*
C60.1962 (4)0.67122 (17)0.0824 (2)0.0419 (10)
C70.1802 (4)0.58830 (17)0.0388 (2)0.0393 (9)
C80.1595 (4)0.54227 (15)−0.0147 (2)0.0391 (10)
H8A0.07300.5460−0.04850.047*
H8B0.23330.5405−0.04540.047*
C90.1768 (4)0.44668 (16)−0.0084 (2)0.0408 (10)
H9A0.24850.4511−0.04010.049*
H9B0.09240.4365−0.04090.049*
C100.2155 (4)0.40456 (17)0.0506 (2)0.0387 (10)
C110.2612 (4)0.32574 (17)0.1022 (2)0.0414 (10)
C120.2816 (4)0.27105 (17)0.1189 (3)0.0480 (11)
H12A0.25260.24370.08330.058*
C130.3455 (4)0.2593 (2)0.1892 (3)0.0523 (12)
H13A0.36230.22280.20300.063*
C140.3872 (5)0.3002 (2)0.2416 (3)0.0539 (12)
H14A0.43230.29050.28980.065*
C150.3647 (4)0.35295 (18)0.2253 (2)0.0461 (11)
H15A0.39080.38000.26170.055*
C160.3016 (4)0.36626 (17)0.1529 (2)0.0392 (10)
C170.5414 (7)0.5170 (4)0.2839 (4)0.111 (3)
H17A0.58430.51870.23790.134*
H17B0.57750.48480.31250.134*
C180.5828 (9)0.5670 (4)0.3312 (6)0.158 (4)
H18A0.68090.56780.34450.237*
H18B0.54130.56590.37710.237*
H18C0.55270.59930.30240.237*
C190.0450 (6)0.5308 (2)0.2460 (4)0.0798 (18)
H19A0.07270.56740.23280.096*
H19B0.07940.52490.29980.096*
C20−0.1021 (6)0.5284 (3)0.2355 (4)0.099 (2)
H20A−0.13650.55550.26740.148*
H20B−0.13070.49260.24930.148*
H20C−0.13750.53560.18280.148*
O50.5161 (3)0.41792 (12)0.00890 (15)0.0447 (7)
O60.3795 (4)0.40081 (15)−0.1255 (2)0.0732 (11)
O70.3734 (4)0.32152 (15)−0.1712 (2)0.0725 (11)
O80.5357 (7)0.16990 (18)−0.0341 (4)0.126 (2)
O90.6222 (7)0.17536 (18)0.0825 (4)0.136 (2)
O100.7047 (3)0.34095 (14)0.1990 (2)0.0673 (10)
O110.6462 (4)0.41649 (13)0.1475 (2)0.0643 (9)
N50.4079 (4)0.35240 (16)−0.1193 (2)0.0524 (10)
N60.5727 (7)0.1957 (2)0.0240 (4)0.102 (2)
N70.6505 (4)0.36722 (16)0.1451 (2)0.0509 (10)
C210.5280 (4)0.36791 (18)0.0124 (2)0.0419 (10)
C220.4763 (5)0.33195 (17)−0.0490 (3)0.0465 (11)
C230.4907 (5)0.2772 (2)−0.0454 (3)0.0614 (14)
H23A0.45600.2555−0.08720.074*
C240.5567 (5)0.25352 (19)0.0198 (3)0.0629 (14)
C250.6078 (5)0.28421 (19)0.0812 (3)0.0576 (13)
H25A0.65330.26760.12520.069*
C260.5921 (4)0.33915 (17)0.0778 (3)0.0458 (11)
N80.9544 (5)0.17124 (16)0.1081 (3)0.0783 (15)
N91.1077 (4)0.21015 (19)0.3675 (2)0.0564 (11)
O120.9230 (4)0.28313 (12)0.08169 (19)0.0605 (9)
O130.9718 (8)0.1816 (3)0.0434 (3)0.075 (3)*0.577 (11)
O140.9109 (8)0.1275 (2)0.1270 (4)0.081 (3)*0.577 (11)
O13A0.8804 (10)0.1802 (4)0.0484 (5)0.083 (4)*0.423 (11)
O14A0.9955 (13)0.1244 (3)0.1159 (7)0.097 (4)*0.423 (11)
O151.1017 (3)0.16073 (15)0.3786 (2)0.0662 (10)
O161.1480 (4)0.24173 (17)0.4180 (2)0.0685 (10)
O171.0423 (3)0.38875 (13)0.25535 (19)0.0590 (9)
O180.9626 (3)0.38007 (12)0.13932 (18)0.0517 (8)
C270.9682 (4)0.26778 (18)0.1456 (3)0.0481 (11)
C280.9854 (5)0.21100 (18)0.1660 (3)0.0523 (12)
C291.0283 (5)0.19286 (19)0.2356 (3)0.0538 (12)
H29A1.03400.15530.24530.065*
C301.0641 (4)0.22935 (19)0.2930 (3)0.0472 (11)
C311.0545 (4)0.28391 (18)0.2804 (3)0.0459 (11)
H31A1.07930.30850.32040.055*
C321.0087 (4)0.30245 (17)0.2095 (3)0.0429 (10)
N101.0031 (3)0.36034 (15)0.2009 (2)0.0456 (9)
O190.7129 (15)0.0593 (3)−0.0039 (7)0.280 (6)
H190.66220.0906−0.01200.420*
C330.8305 (13)0.0560 (5)−0.0371 (9)0.292 (14)
H33A0.84460.0190−0.05470.351*
H33B0.91030.0672−0.00160.351*
C340.8024 (13)0.0960 (5)−0.1043 (6)0.169 (5)
H34A0.87830.0956−0.13270.253*
H34B0.79090.1324−0.08530.253*
H34C0.72020.0851−0.13720.253*
O200.7010 (7)−0.0141 (3)0.1132 (3)0.141 (2)
H200.70560.00990.07420.211*
C350.6637 (14)−0.0651 (4)0.0749 (6)0.173 (5)
H35A0.6185−0.08780.10870.208*
H35B0.5970−0.05730.03000.208*
C360.7723 (13)−0.0961 (6)0.0511 (8)0.214 (6)
H36A0.7349−0.12710.02160.320*
H36B0.8329−0.10860.09540.320*
H36C0.8224−0.07350.02040.320*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn0.0467 (4)0.0440 (4)0.0288 (4)0.0027 (3)0.0021 (3)0.0021 (3)
O10.0509 (17)0.0410 (16)0.0441 (19)0.0022 (12)0.0094 (14)−0.0005 (12)
O20.069 (2)0.097 (3)0.037 (2)0.0132 (19)−0.0015 (17)−0.0032 (18)
O30.072 (2)0.0499 (19)0.063 (2)−0.0003 (15)0.0297 (19)−0.0059 (15)
O40.0453 (16)0.0409 (16)0.0264 (15)−0.0014 (12)0.0004 (12)0.0018 (11)
N10.046 (2)0.046 (2)0.029 (2)0.0010 (16)0.0013 (15)0.0035 (16)
N20.0444 (19)0.0419 (19)0.034 (2)0.0032 (16)0.0049 (15)0.0081 (16)
N30.0424 (18)0.0445 (19)0.0288 (19)0.0023 (16)0.0039 (15)0.0025 (15)
N40.049 (2)0.0394 (19)0.033 (2)−0.0035 (16)0.0043 (16)−0.0026 (15)
C10.040 (2)0.044 (2)0.040 (3)−0.0014 (19)0.0064 (18)0.0005 (19)
C20.053 (3)0.055 (3)0.037 (3)0.001 (2)0.005 (2)−0.001 (2)
C30.052 (3)0.055 (3)0.048 (3)−0.006 (2)0.005 (2)−0.012 (2)
C40.053 (3)0.046 (3)0.057 (3)−0.005 (2)0.013 (2)−0.005 (2)
C50.050 (3)0.041 (2)0.050 (3)−0.003 (2)0.013 (2)0.004 (2)
C60.039 (2)0.047 (2)0.040 (3)−0.0027 (19)0.0091 (19)0.000 (2)
C70.040 (2)0.044 (2)0.035 (2)−0.0012 (18)0.0080 (18)0.0044 (19)
C80.047 (2)0.039 (2)0.030 (2)0.0014 (18)0.0031 (18)0.0055 (18)
C90.046 (2)0.045 (2)0.031 (2)0.0011 (19)0.0054 (18)0.0008 (19)
C100.041 (2)0.044 (2)0.031 (2)−0.0023 (18)0.0054 (18)−0.0025 (18)
C110.041 (2)0.049 (3)0.036 (2)0.0030 (19)0.0106 (19)0.0059 (19)
C120.053 (3)0.043 (2)0.049 (3)0.002 (2)0.012 (2)0.005 (2)
C130.054 (3)0.051 (3)0.055 (3)0.006 (2)0.016 (2)0.013 (2)
C140.055 (3)0.063 (3)0.044 (3)0.009 (2)0.009 (2)0.017 (2)
C150.052 (3)0.050 (3)0.035 (2)0.004 (2)0.004 (2)0.005 (2)
C160.042 (2)0.040 (2)0.036 (2)0.0058 (18)0.0070 (18)0.0012 (18)
C170.089 (5)0.165 (7)0.072 (5)0.017 (5)−0.015 (4)−0.028 (5)
C180.110 (7)0.207 (10)0.143 (9)0.032 (6)−0.029 (6)−0.047 (8)
C190.081 (4)0.074 (4)0.094 (5)−0.004 (3)0.046 (4)−0.025 (3)
C200.076 (4)0.118 (6)0.102 (6)0.016 (4)0.014 (4)−0.016 (4)
O50.0531 (18)0.0412 (17)0.0388 (18)0.0014 (13)0.0033 (14)−0.0009 (13)
O60.090 (3)0.060 (2)0.060 (2)−0.010 (2)−0.0173 (19)−0.0121 (19)
O70.074 (2)0.077 (2)0.066 (3)−0.0082 (19)0.0099 (19)−0.038 (2)
O80.185 (6)0.047 (3)0.154 (6)−0.004 (3)0.049 (4)−0.016 (3)
O90.215 (7)0.048 (3)0.142 (5)0.018 (3)0.022 (5)0.026 (3)
O100.065 (2)0.073 (2)0.062 (2)0.0082 (17)0.0048 (18)0.0288 (19)
O110.081 (2)0.049 (2)0.054 (2)0.0006 (17)−0.0159 (18)0.0049 (16)
N50.053 (2)0.052 (2)0.054 (3)−0.0099 (19)0.0130 (19)−0.015 (2)
N60.148 (6)0.040 (3)0.125 (6)−0.006 (3)0.047 (5)−0.003 (3)
N70.048 (2)0.055 (2)0.050 (3)0.0026 (19)0.0088 (18)0.015 (2)
C210.041 (2)0.043 (3)0.043 (3)−0.0030 (19)0.0125 (19)−0.0008 (19)
C220.050 (3)0.043 (3)0.050 (3)0.000 (2)0.017 (2)−0.006 (2)
C230.068 (3)0.052 (3)0.072 (4)−0.011 (2)0.033 (3)−0.017 (3)
C240.071 (3)0.039 (3)0.086 (4)0.002 (2)0.033 (3)0.007 (3)
C250.058 (3)0.049 (3)0.071 (4)0.000 (2)0.026 (3)0.012 (3)
C260.044 (2)0.043 (2)0.054 (3)−0.0011 (19)0.016 (2)0.003 (2)
N80.126 (4)0.042 (2)0.059 (3)−0.009 (2)−0.012 (3)0.017 (2)
N90.047 (2)0.070 (3)0.053 (3)0.011 (2)0.010 (2)0.027 (2)
O120.082 (2)0.0488 (18)0.046 (2)−0.0060 (17)−0.0055 (17)0.0109 (15)
O150.060 (2)0.078 (3)0.062 (2)0.0123 (18)0.0136 (17)0.0355 (19)
O160.074 (2)0.087 (3)0.043 (2)0.017 (2)0.0025 (18)0.011 (2)
O170.078 (2)0.0529 (19)0.043 (2)−0.0001 (16)0.0018 (17)0.0019 (16)
O180.0632 (19)0.0477 (18)0.0436 (19)0.0062 (14)0.0056 (15)0.0143 (15)
C270.051 (3)0.049 (3)0.042 (3)0.001 (2)−0.001 (2)0.014 (2)
C280.063 (3)0.045 (3)0.049 (3)−0.007 (2)0.006 (2)0.007 (2)
C290.057 (3)0.048 (3)0.056 (3)0.001 (2)0.006 (2)0.019 (2)
C300.045 (2)0.055 (3)0.041 (3)0.004 (2)0.007 (2)0.015 (2)
C310.043 (2)0.055 (3)0.040 (3)0.008 (2)0.0060 (19)0.010 (2)
C320.040 (2)0.046 (2)0.044 (3)0.0045 (19)0.0096 (19)0.009 (2)
N100.044 (2)0.050 (2)0.043 (2)0.0028 (17)0.0068 (17)0.0086 (19)
O190.45 (2)0.109 (6)0.316 (15)−0.045 (9)0.159 (14)−0.037 (7)
C330.189 (13)0.151 (13)0.57 (4)−0.059 (11)0.17 (2)−0.138 (18)
C340.245 (14)0.125 (8)0.140 (10)−0.038 (8)0.036 (9)0.005 (7)
O200.195 (7)0.160 (5)0.072 (4)−0.043 (4)0.035 (4)−0.030 (3)
C350.260 (15)0.138 (9)0.127 (9)−0.058 (9)0.047 (9)−0.050 (7)
C360.172 (11)0.272 (16)0.184 (13)0.080 (11)−0.015 (9)−0.025 (12)

Geometric parameters (Å, °)

Mn—O22.123 (4)C19—H19B0.9900
Mn—O12.140 (3)C20—H20A0.9800
Mn—O32.194 (3)C20—H20B0.9800
Mn—N12.199 (3)C20—H20C0.9800
Mn—N32.215 (3)O5—C211.250 (5)
Mn—O42.384 (3)O6—N51.238 (5)
O1—H1W0.9300O7—N51.220 (5)
O1—H2W0.9301O8—N61.236 (8)
O2—C171.449 (8)O9—N61.209 (8)
O2—H20.9500O10—N71.229 (5)
O3—C191.404 (6)O11—N71.227 (5)
O3—H30.9500N5—C221.443 (6)
O4—C91.425 (5)N6—C241.448 (7)
O4—C81.429 (5)N7—C261.446 (6)
N1—C71.320 (5)C21—C261.447 (6)
N1—C11.396 (5)C21—C221.457 (6)
N2—C71.348 (5)C22—C231.370 (6)
N2—C61.386 (5)C23—C241.392 (8)
N2—H2B0.8800C23—H23A0.9500
N3—C101.314 (5)C24—C251.379 (7)
N3—C161.386 (5)C25—C261.375 (6)
N4—C101.331 (5)C25—H25A0.9500
N4—C111.389 (5)N8—O131.232 (5)
N4—H4B0.8800N8—O14A1.236 (5)
C1—C61.393 (6)N8—O13A1.236 (5)
C1—C21.401 (6)N8—O141.239 (5)
C2—C31.369 (6)N8—C281.437 (6)
C2—H2A0.9500N9—O161.224 (5)
C3—C41.400 (7)N9—O151.247 (5)
C3—H3A0.9500N9—C301.433 (6)
C4—C51.369 (6)O12—C271.235 (5)
C4—H4A0.9500O17—N101.226 (5)
C5—C61.392 (6)O18—N101.227 (4)
C5—H5A0.9500C27—C321.448 (6)
C7—C81.491 (6)C27—C281.462 (6)
C8—H8A0.9900C28—C291.344 (6)
C8—H8B0.9900C29—C301.383 (7)
C9—C101.502 (6)C29—H29A0.9500
C9—H9A0.9900C30—C311.376 (6)
C9—H9B0.9900C31—C321.373 (6)
C11—C161.381 (6)C31—H31A0.9500
C11—C121.401 (6)C32—N101.448 (6)
C12—C131.365 (7)O19—C331.404 (9)
C12—H12A0.9500O19—H190.9299
C13—C141.409 (7)C33—C341.560 (10)
C13—H13A0.9500C33—H33A0.9900
C14—C151.356 (6)C33—H33B0.9900
C14—H14A0.9500C34—H34A0.9800
C15—C161.403 (6)C34—H34B0.9800
C15—H15A0.9500C34—H34C0.9800
C17—C181.531 (11)O20—C351.466 (10)
C17—H17A0.9900O20—H200.9296
C17—H17B0.9900C35—C361.451 (14)
C18—H18A0.9800C35—H35A0.9900
C18—H18B0.9800C35—H35B0.9900
C18—H18C0.9800C36—H36A0.9800
C19—C201.464 (8)C36—H36B0.9800
C19—H19A0.9900C36—H36C0.9800
O2—Mn—O194.95 (14)C17—C18—H18C109.5
O2—Mn—O388.13 (15)H18A—C18—H18C109.5
O1—Mn—O3175.05 (11)H18B—C18—H18C109.5
O2—Mn—N1107.83 (13)O3—C19—C20114.3 (5)
O1—Mn—N189.80 (12)O3—C19—H19A108.7
O3—Mn—N192.95 (12)C20—C19—H19A108.7
O2—Mn—N3110.56 (13)O3—C19—H19B108.7
O1—Mn—N386.88 (11)C20—C19—H19B108.7
O3—Mn—N388.41 (12)H19A—C19—H19B107.6
N1—Mn—N3141.62 (13)C19—C20—H20A109.5
O2—Mn—O4177.23 (12)C19—C20—H20B109.5
O1—Mn—O487.29 (11)H20A—C20—H20B109.5
O3—Mn—O489.76 (12)C19—C20—H20C109.5
N1—Mn—O470.50 (11)H20A—C20—H20C109.5
N3—Mn—O471.15 (10)H20B—C20—H20C109.5
Mn—O1—H1W120.2O7—N5—O6120.5 (4)
Mn—O1—H2W118.7O7—N5—C22119.8 (4)
H1W—O1—H2W121.1O6—N5—C22119.7 (4)
C17—O2—Mn128.3 (4)O9—N6—O8123.8 (6)
C17—O2—H2115.8O9—N6—C24119.2 (7)
Mn—O2—H2115.8O8—N6—C24117.0 (7)
C19—O3—Mn128.7 (3)O11—N7—O10121.1 (4)
C19—O3—H3115.6O11—N7—C26120.0 (4)
Mn—O3—H3115.6O10—N7—C26118.9 (4)
C9—O4—C8113.3 (3)O5—C21—C26124.1 (4)
C9—O4—Mn114.9 (2)O5—C21—C22123.4 (4)
C8—O4—Mn115.1 (2)C26—C21—C22112.5 (4)
C7—N1—C1105.4 (3)C23—C22—N5115.1 (4)
C7—N1—Mn118.6 (3)C23—C22—C21123.4 (5)
C1—N1—Mn136.0 (3)N5—C22—C21121.4 (4)
C7—N2—C6107.4 (4)C22—C23—C24119.5 (5)
C7—N2—H2B126.3C22—C23—H23A120.2
C6—N2—H2B126.3C24—C23—H23A120.2
C10—N3—C16104.9 (3)C25—C24—C23121.2 (5)
C10—N3—Mn117.7 (3)C25—C24—N6118.9 (6)
C16—N3—Mn137.4 (3)C23—C24—N6119.9 (6)
C10—N4—C11107.1 (3)C26—C25—C24119.2 (5)
C10—N4—H4B126.4C26—C25—H25A120.4
C11—N4—H4B126.4C24—C25—H25A120.4
C6—C1—N1109.1 (4)C25—C26—N7114.4 (4)
C6—C1—C2120.4 (4)C25—C26—C21124.1 (5)
N1—C1—C2130.4 (4)N7—C26—C21121.5 (4)
C3—C2—C1116.6 (4)O13—N8—O14A102.2 (8)
C3—C2—H2A121.7O13—N8—O13A44.6 (5)
C1—C2—H2A121.7O14A—N8—O13A114.6 (8)
C2—C3—C4122.5 (5)O13—N8—O14123.2 (6)
C2—C3—H3A118.7O14A—N8—O1442.9 (5)
C4—C3—H3A118.7O13A—N8—O14101.8 (7)
C5—C4—C3121.5 (4)O13—N8—C28119.9 (5)
C5—C4—H4A119.2O14A—N8—C28122.2 (7)
C3—C4—H4A119.2O13A—N8—C28123.2 (6)
C4—C5—C6116.4 (4)O14—N8—C28116.9 (5)
C4—C5—H5A121.8O16—N9—O15122.1 (4)
C6—C5—H5A121.8O16—N9—C30120.3 (4)
N2—C6—C5131.9 (4)O15—N9—C30117.6 (5)
N2—C6—C1105.5 (4)O12—C27—C32125.4 (4)
C5—C6—C1122.5 (4)O12—C27—C28123.1 (4)
N1—C7—N2112.6 (4)C32—C27—C28111.5 (4)
N1—C7—C8123.0 (4)C29—C28—N8116.9 (4)
N2—C7—C8124.2 (4)C29—C28—C27124.6 (5)
O4—C8—C7105.5 (3)N8—C28—C27118.5 (4)
O4—C8—H8A110.6C28—C29—C30119.4 (4)
C7—C8—H8A110.6C28—C29—H29A120.3
O4—C8—H8B110.6C30—C29—H29A120.3
C7—C8—H8B110.6C31—C30—C29121.3 (4)
H8A—C8—H8B108.8C31—C30—N9119.1 (4)
O4—C9—C10106.1 (3)C29—C30—N9119.5 (4)
O4—C9—H9A110.5C32—C31—C30119.3 (4)
C10—C9—H9A110.5C32—C31—H31A120.3
O4—C9—H9B110.5C30—C31—H31A120.3
C10—C9—H9B110.5C31—C32—N10115.8 (4)
H9A—C9—H9B108.7C31—C32—C27123.9 (4)
N3—C10—N4113.2 (4)N10—C32—C27120.3 (4)
N3—C10—C9123.4 (4)O17—N10—O18121.2 (4)
N4—C10—C9123.3 (4)O17—N10—C32119.0 (4)
C16—C11—N4105.1 (4)O18—N10—C32119.8 (4)
C16—C11—C12123.1 (4)C33—O19—H19117.3
N4—C11—C12131.8 (4)O19—C33—C34103.1 (11)
C13—C12—C11116.2 (4)O19—C33—H33A111.1
C13—C12—H12A121.9C34—C33—H33A111.1
C11—C12—H12A121.9O19—C33—H33B111.1
C12—C13—C14121.4 (4)C34—C33—H33B111.1
C12—C13—H13A119.3H33A—C33—H33B109.1
C14—C13—H13A119.3C33—C34—H34A109.5
C15—C14—C13122.0 (4)C33—C34—H34B109.5
C15—C14—H14A119.0H34A—C34—H34B109.5
C13—C14—H14A119.0C33—C34—H34C109.5
C14—C15—C16117.9 (4)H34A—C34—H34C109.5
C14—C15—H15A121.1H34B—C34—H34C109.5
C16—C15—H15A121.1C35—O20—H20103.7
C11—C16—N3109.6 (4)C36—C35—O20116.6 (12)
C11—C16—C15119.5 (4)C36—C35—H35A108.2
N3—C16—C15130.9 (4)O20—C35—H35A108.2
O2—C17—C18115.4 (6)C36—C35—H35B108.2
O2—C17—H17A108.4O20—C35—H35B108.2
C18—C17—H17A108.4H35A—C35—H35B107.3
O2—C17—H17B108.4C35—C36—H36A109.5
C18—C17—H17B108.4C35—C36—H36B109.5
H17A—C17—H17B107.5H36A—C36—H36B109.5
C17—C18—H18A109.5C35—C36—H36C109.5
C17—C18—H18B109.5H36A—C36—H36C109.5
H18A—C18—H18B109.5H36B—C36—H36C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1W···O5i0.931.992.758 (4)139.
O1—H1W···O6i0.932.072.854 (4)141.
O1—H2W···O50.931.992.758 (4)139.
O1—H2W···O110.932.112.898 (4)141.
O2—H2···O20ii0.951.762.659 (7)157.
O3—H3···O17iii0.952.092.864 (4)138.
O3—H3···O18iii0.952.373.289 (5)163.
N2—H2B···O12i0.881.922.676 (4)142.
N2—H2B···O18i0.882.252.973 (5)140.
N4—H4B···O15iv0.882.102.907 (5)152.
N4—H4B···O16iv0.882.383.161 (5)148.
O19—H19···O80.932.353.278 (13)179.
O20—H20···O190.931.882.807 (13)179.

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) x−1, y, z; (iv) x−1, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5083).

References

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  • Chang, C. M., Kulkarni, M. V., Chen, C. H., Wang, C. & Sun, C. M. (2008). J. Comb. Chem.10, 466–474. [PubMed]
  • Harrell, C. C., Kohli, P., Siwy, Z. & Martin, C. R. (2004). J. Am. Chem. Soc.126, 15646–15647. [PubMed]
  • Holland, P. L. & Tolman, W. B. (2000). J. Am. Chem. Soc.122, 6331–6332.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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