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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m75.
Published online 2008 December 17. doi:  10.1107/S1600536808041640
PMCID: PMC2967912

Bis(1-methyl-1H-imidazole-κN 3)[N,N′-o-phenyl­enebis(pyridine-2-carbox­amido)-κ4 N]manganese(II)

Abstract

The title compound, [Mn(C18H12N4O2)(C4H6N2)2], belongs to the family of 1,2-bis­(pyridine-2-carboxamido)benzene (H2bpb) ligated metal complexes. The manganese center is octa­hedrally coordinated by a bpb ligand and two axial 1-methyl­imidazole mol­ecules. The axial N—Mn—N group is bent with a bond angle of 151.79 (7)°.

Related literature

For the structures of related Mn complexes, see Liang et al. (2007 [triangle]), Lin et al. (2003 [triangle]), and Havranek et al. (1999 [triangle]).

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Object name is e-65-00m75-scheme1.jpg

Experimental

Crystal data

  • [Mn(C18H12N4O2)(C4H6N2)2]
  • M r = 535.47
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m75-efi1.jpg
  • a = 13.819 (3) Å
  • b = 9.894 (2) Å
  • c = 17.864 (4) Å
  • V = 2442.5 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.58 mm−1
  • T = 100 (2) K
  • 0.54 × 0.35 × 0.04 mm

Data collection

  • Bruker APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007 [triangle]) T min = 0.744, T max = 0.977
  • 8288 measured reflections
  • 3473 independent reflections
  • 3301 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.062
  • S = 1.02
  • 3473 reflections
  • 335 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.19 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 989 Friedel pairs
  • Flack parameter: 0.046 (17)

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041640/pk2130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041640/pk2130Isup2.hkl

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

Acknowledgments

This work was supported by the National Science Foundation (CHE-0079282 and CHE-0076640). The authors thank the National Science Foundation (CHE-0130835) and the University of Oklahoma for funds to acquire the diffractometer and computers used in this work.

supplementary crystallographic information

Comment

In this paper, we report the structure of the title compound, a six-coordinate {bis(1-methylimidazole)}(bpb)manganese(II) (H2bpb = 1,2-bis(pyridine-2-carboxamido)benzene). To the best of our knowledge, this is the first reported structure of a Mn(II) complex containing ligated bpb or its derivatives. The structures of the related [Mn(bpb)(H2O)Cl] (Lin et al. 2003), [Mn(bpc)(DMF)Cl] (H2bpc = 1,2-bis(pyridine-2-carboxamido)-4,5-dichlorobenzene) (Liang et al.,2007) and [Mn(bpmb)(OMe)(OCOCH3)] (H2bpmb = N,N'-bis(pyridine-2-ylcarbonyl)-4-methoxycarbonylbenzene-1,2-diamine) (Havranek et al., 1999) complexes have been reported previously.

The molecular structure is shown in Fig. 1. The manganese center is six-coordinate, displaying a distorted octahedral geometry. A bpb ligand binds to the manganese through its two deprotonated amide N atoms and two pyridyl N atoms. The two axial positions are occupied by 1-methylimidazole molecules. The Mn—N(pyridyl) distances of 2.2621 (19) Å and 2.2684 (19)Å are longer than the Mn—N(amide) distances at 2.1764 (19) Å and 2.1794 (18) Å. Both of the Mn—N(pyridyl) and Mn—N(amide) distances are significantly longer than those in the related Mn complexes reported previously (Liang et al., 2007; Lin et al., 2003; Havranek et al., 1999). In addition, the C13—C14 and C21—C22 distances of 1.513 (3) Å and 1.526 (3) Å are slightly longer than those of the other Mn complexes mentioned above. Mn—N(1-methylimidazole) distances are 2.2552 (19) Å and 2.280 (2) Å. The axial N—Mn—N linkage is bent with a bond angle of 151.79 (7)°.

Experimental

To a CH2Cl2 suspension (20 ml) of Mn(bpb)Cl (0.2 g, 0.49 mmol) was added excess piperidine (2 ml, 0.02 mol) (Aldrich Chemical Company, used as received) and then purged with nitric oxide (98%; Matheson Gas, purified by passing through KOH pellets and a cold trap (dry ice/acetone)) for 30 min. This resulted in the precipitation of a red-brown intermediate Mn(bpb)(NO)(pip) (νNO 1732 cm-1; KBr pellet) that was isolated by filtration. This intermediate was redissolved in CH2Cl2, and excess 1-methylimidazole (0.2 ml, 2.6 mmol) (Aldrich Chemical Company, used as received) was added. The resulting mixture was stirred for 30 min. A brown solid was obtained after removal of the solvent under vacuum. A suitable red plate-shaped crystal was grown by slow evaporation of a CH2Cl2 solution of the complex in the presence of excess 1-methylimidazole at room temperature under N2.

Refinement

H atoms were positioned geometrically and refined using a riding model with C—H = 0.95 Å for aromatic carbons, 0.98 Å for methyl carbons. Uiso(H) values were set to either 1.5Ueq (RCH3) or 1.2Ueq of the attached atom.

Figures

Fig. 1.
The molecular structure showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 35% probability level (H atoms omitted for clarity).

Crystal data

[Mn(C18H12N4O2)(C4H6N2)2]F(000) = 1108
Mr = 535.47Dx = 1.456 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 6910 reflections
a = 13.819 (3) Åθ = 2.5–28.3°
b = 9.894 (2) ŵ = 0.58 mm1
c = 17.864 (4) ÅT = 100 K
V = 2442.5 (9) Å3Plate, red
Z = 40.54 × 0.35 × 0.04 mm

Data collection

Bruker APEX diffractometer3473 independent reflections
Radiation source: fine-focus sealed tube3301 reflections with I > 2σ(I)
graphiteRint = 0.022
ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)h = −16→17
Tmin = 0.744, Tmax = 0.977k = −12→7
8288 measured reflectionsl = −22→13

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.062w = 1/[σ2(Fo2) + (0.038P)2 + 0.1P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3473 reflectionsΔρmax = 0.33 e Å3
335 parametersΔρmin = −0.19 e Å3
1 restraintAbsolute structure: Flack (1983), 989 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.046 (17)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Mn10.38539 (2)0.37818 (3)0.51871 (2)0.01386 (8)
O10.36109 (12)0.12118 (15)0.32716 (9)0.0186 (3)
O20.65501 (11)0.32649 (17)0.63464 (9)0.0236 (4)
N10.30418 (13)0.22376 (19)0.58708 (11)0.0194 (4)
N20.19272 (14)0.08610 (19)0.63164 (11)0.0201 (4)
N30.40259 (14)0.58964 (19)0.46979 (11)0.0185 (4)
N40.41706 (15)0.74233 (19)0.38026 (12)0.0204 (4)
N50.25565 (14)0.37585 (17)0.44149 (10)0.0157 (4)
N60.42608 (13)0.24628 (19)0.42643 (11)0.0151 (4)
N70.53284 (12)0.31457 (18)0.54386 (10)0.0156 (4)
N80.42419 (13)0.48437 (18)0.62717 (10)0.0156 (4)
C10.21158 (16)0.1926 (2)0.58814 (13)0.0206 (5)
H10.16350.24050.56100.025*
C20.27962 (17)0.0447 (3)0.66076 (15)0.0283 (6)
H20.2902−0.02940.69350.034*
C30.34717 (18)0.1303 (2)0.63362 (15)0.0260 (5)
H30.41430.12670.64490.031*
C40.09803 (17)0.0263 (3)0.64689 (15)0.0266 (5)
H4A0.05200.05490.60830.040*
H4B0.07510.05640.69610.040*
H4C0.1035−0.07240.64650.040*
C50.38396 (16)0.6197 (2)0.39912 (15)0.0183 (5)
H50.35090.56110.36560.022*
C60.45966 (18)0.7961 (2)0.44268 (14)0.0239 (5)
H60.48960.88220.44700.029*
C70.45043 (16)0.7012 (2)0.49738 (13)0.0216 (5)
H70.47350.71050.54720.026*
C80.4078 (2)0.8059 (2)0.30677 (15)0.0271 (5)
H8A0.37260.74530.27300.041*
H8B0.47240.82390.28630.041*
H8C0.37230.89120.31170.041*
C90.17954 (16)0.4603 (2)0.44273 (13)0.0183 (5)
H90.17000.51500.48580.022*
C100.11453 (15)0.4712 (2)0.38434 (14)0.0200 (5)
H100.06230.53340.38650.024*
C110.12757 (17)0.3891 (2)0.32266 (15)0.0206 (5)
H110.08350.39320.28190.025*
C120.20533 (16)0.3006 (2)0.32047 (13)0.0188 (5)
H120.21490.24300.27850.023*
C130.26922 (15)0.2974 (2)0.38068 (13)0.0158 (4)
C140.35901 (16)0.2101 (2)0.37724 (12)0.0147 (4)
C150.51905 (15)0.1872 (2)0.43010 (13)0.0151 (4)
C160.55961 (17)0.1028 (2)0.37494 (14)0.0178 (5)
H160.52240.07870.33230.021*
C170.65348 (17)0.0543 (2)0.38227 (14)0.0212 (5)
H170.6800−0.00260.34470.025*
C180.70854 (17)0.0888 (2)0.44413 (14)0.0216 (5)
H180.77230.05420.44920.026*
C190.67119 (15)0.1736 (2)0.49883 (13)0.0193 (5)
H190.71020.19780.54050.023*
C200.57629 (15)0.2242 (2)0.49336 (13)0.0163 (5)
C210.57588 (16)0.3589 (2)0.60555 (13)0.0171 (5)
C220.51797 (15)0.4679 (2)0.64610 (12)0.0160 (4)
C230.56201 (16)0.5497 (2)0.69906 (13)0.0200 (5)
H230.62800.53630.71190.024*
C240.50893 (18)0.6512 (2)0.73299 (13)0.0234 (5)
H240.53850.71000.76830.028*
C250.41228 (18)0.6657 (2)0.71479 (14)0.0213 (5)
H250.37370.73280.73830.026*
C260.37272 (17)0.5799 (2)0.66128 (14)0.0187 (5)
H260.30630.58980.64860.022*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.01291 (14)0.01638 (15)0.01230 (15)−0.00013 (12)−0.00020 (14)−0.00077 (16)
O10.0198 (8)0.0179 (8)0.0181 (9)−0.0009 (6)0.0002 (7)−0.0041 (7)
O20.0145 (8)0.0335 (9)0.0227 (9)0.0036 (7)−0.0046 (7)−0.0034 (8)
N10.0194 (10)0.0207 (10)0.0181 (10)−0.0003 (8)0.0007 (8)0.0018 (8)
N20.0224 (10)0.0204 (10)0.0175 (10)−0.0027 (8)0.0029 (8)−0.0006 (8)
N30.0208 (10)0.0178 (9)0.0170 (10)0.0010 (7)0.0003 (8)0.0005 (8)
N40.0258 (10)0.0165 (10)0.0188 (10)0.0017 (8)0.0023 (8)0.0012 (8)
N50.0172 (9)0.0148 (9)0.0149 (10)−0.0009 (7)0.0003 (8)0.0010 (7)
N60.0153 (9)0.0161 (8)0.0138 (9)0.0004 (7)0.0029 (7)0.0003 (7)
N70.0120 (9)0.0188 (9)0.0161 (9)0.0009 (7)0.0013 (7)0.0014 (7)
N80.0171 (9)0.0181 (9)0.0116 (9)−0.0019 (7)0.0007 (7)0.0020 (8)
C10.0217 (12)0.0219 (12)0.0181 (12)−0.0003 (10)0.0002 (9)0.0028 (9)
C20.0294 (13)0.0272 (13)0.0282 (14)0.0023 (10)0.0008 (11)0.0096 (11)
C30.0206 (12)0.0314 (14)0.0259 (13)0.0031 (10)−0.0013 (11)0.0050 (11)
C40.0241 (12)0.0291 (13)0.0266 (13)−0.0073 (10)0.0035 (10)0.0032 (11)
C50.0177 (12)0.0151 (12)0.0220 (13)−0.0017 (8)0.0020 (9)−0.0010 (9)
C60.0309 (13)0.0188 (11)0.0220 (13)−0.0047 (10)0.0013 (10)0.0000 (10)
C70.0231 (11)0.0213 (12)0.0203 (12)−0.0039 (9)0.0017 (9)−0.0002 (9)
C80.0400 (15)0.0218 (12)0.0197 (12)0.0026 (11)0.0031 (11)0.0045 (10)
C90.0183 (11)0.0192 (11)0.0174 (11)0.0009 (9)0.0038 (9)−0.0002 (9)
C100.0158 (11)0.0207 (11)0.0235 (12)0.0008 (9)0.0015 (9)0.0040 (10)
C110.0188 (12)0.0225 (12)0.0206 (12)−0.0035 (9)−0.0038 (9)0.0054 (10)
C120.0213 (12)0.0187 (11)0.0163 (11)−0.0027 (9)0.0005 (9)−0.0002 (9)
C130.0178 (11)0.0124 (10)0.0172 (11)−0.0039 (8)0.0033 (9)−0.0002 (9)
C140.0177 (11)0.0132 (10)0.0131 (10)−0.0025 (8)0.0019 (9)0.0041 (9)
C150.0161 (11)0.0143 (10)0.0151 (11)−0.0006 (8)0.0021 (9)0.0032 (9)
C160.0218 (12)0.0164 (11)0.0153 (11)−0.0013 (9)0.0025 (9)−0.0013 (9)
C170.0240 (12)0.0187 (12)0.0209 (12)0.0018 (10)0.0070 (10)−0.0015 (10)
C180.0142 (11)0.0224 (12)0.0283 (13)0.0030 (9)0.0036 (10)0.0029 (10)
C190.0145 (10)0.0216 (11)0.0218 (13)0.0010 (8)0.0004 (9)0.0027 (9)
C200.0148 (10)0.0166 (10)0.0173 (11)−0.0028 (8)0.0019 (8)0.0033 (9)
C210.0144 (11)0.0212 (12)0.0157 (11)−0.0030 (9)0.0007 (9)0.0011 (9)
C220.0171 (10)0.0175 (11)0.0135 (11)−0.0024 (8)0.0025 (8)0.0051 (9)
C230.0174 (11)0.0227 (12)0.0199 (12)−0.0047 (9)−0.0023 (9)0.0004 (10)
C240.0327 (14)0.0209 (12)0.0168 (12)−0.0043 (10)−0.0057 (10)−0.0014 (10)
C250.0278 (12)0.0192 (11)0.0168 (11)0.0025 (9)−0.0008 (10)−0.0006 (10)
C260.0186 (11)0.0192 (11)0.0181 (12)0.0010 (9)−0.0011 (9)0.0017 (10)

Geometric parameters (Å, °)

Mn1—N62.1764 (19)C6—C71.361 (3)
Mn1—N72.1794 (18)C6—H60.9500
Mn1—N12.2552 (19)C7—H70.9500
Mn1—N52.2621 (19)C8—H8A0.9800
Mn1—N82.2684 (19)C8—H8B0.9800
Mn1—N32.280 (2)C8—H8C0.9800
O1—C141.255 (3)C9—C101.381 (3)
O2—C211.252 (3)C9—H90.9500
N1—C11.316 (3)C10—C111.381 (4)
N1—C31.378 (3)C10—H100.9500
N2—C11.335 (3)C11—C121.387 (3)
N2—C21.371 (3)C11—H110.9500
N2—C41.462 (3)C12—C131.392 (3)
N3—C51.322 (3)C12—H120.9500
N3—C71.378 (3)C13—C141.513 (3)
N4—C51.340 (3)C15—C161.408 (3)
N4—C61.369 (3)C15—C201.427 (3)
N4—C81.461 (3)C16—C171.389 (3)
N5—C91.343 (3)C16—H160.9500
N5—C131.348 (3)C17—C181.384 (3)
N6—C141.326 (3)C17—H170.9500
N6—C151.413 (3)C18—C191.387 (3)
N7—C211.327 (3)C18—H180.9500
N7—C201.405 (3)C19—C201.407 (3)
N8—C261.330 (3)C19—H190.9500
N8—C221.349 (3)C21—C221.526 (3)
C1—H10.9500C22—C231.386 (3)
C2—C31.350 (3)C23—C241.383 (3)
C2—H20.9500C23—H230.9500
C3—H30.9500C24—C251.382 (3)
C4—H4A0.9800C24—H240.9500
C4—H4B0.9800C25—C261.390 (4)
C4—H4C0.9800C25—H250.9500
C5—H50.9500C26—H260.9500
N6—Mn1—N775.02 (7)N3—C7—H7125.0
N6—Mn1—N197.62 (7)N4—C8—H8A109.5
N7—Mn1—N199.09 (7)N4—C8—H8B109.5
N6—Mn1—N574.74 (7)H8A—C8—H8B109.5
N7—Mn1—N5149.74 (7)N4—C8—H8C109.5
N1—Mn1—N585.93 (7)H8A—C8—H8C109.5
N6—Mn1—N8149.72 (7)H8B—C8—H8C109.5
N7—Mn1—N874.73 (7)N5—C9—C10123.1 (2)
N1—Mn1—N888.21 (7)N5—C9—H9118.5
N5—Mn1—N8135.47 (7)C10—C9—H9118.5
N6—Mn1—N3103.48 (8)C11—C10—C9118.2 (2)
N7—Mn1—N3104.27 (7)C11—C10—H10120.9
N1—Mn1—N3151.79 (7)C9—C10—H10120.9
N5—Mn1—N381.85 (7)C10—C11—C12119.7 (2)
N8—Mn1—N382.97 (7)C10—C11—H11120.2
C1—N1—C3104.67 (19)C12—C11—H11120.2
C1—N1—Mn1130.57 (15)C11—C12—C13119.0 (2)
C3—N1—Mn1124.52 (15)C11—C12—H12120.5
C1—N2—C2106.58 (19)C13—C12—H12120.5
C1—N2—C4127.1 (2)N5—C13—C12121.4 (2)
C2—N2—C4126.3 (2)N5—C13—C14118.38 (19)
C5—N3—C7104.76 (19)C12—C13—C14120.1 (2)
C5—N3—Mn1123.51 (16)O1—C14—N6130.2 (2)
C7—N3—Mn1130.40 (16)O1—C14—C13116.61 (19)
C5—N4—C6107.1 (2)N6—C14—C13113.10 (19)
C5—N4—C8125.9 (2)C16—C15—N6125.1 (2)
C6—N4—C8127.0 (2)C16—C15—C20119.1 (2)
C9—N5—C13118.7 (2)N6—C15—C20115.75 (19)
C9—N5—Mn1127.17 (15)C17—C16—C15120.7 (2)
C13—N5—Mn1112.77 (14)C17—C16—H16119.7
C14—N6—C15123.67 (19)C15—C16—H16119.7
C14—N6—Mn1118.88 (14)C18—C17—C16120.2 (2)
C15—N6—Mn1116.61 (14)C18—C17—H17119.9
C21—N7—C20123.51 (18)C16—C17—H17119.9
C21—N7—Mn1119.67 (14)C17—C18—C19120.4 (2)
C20—N7—Mn1116.81 (14)C17—C18—H18119.8
C26—N8—C22118.98 (19)C19—C18—H18119.8
C26—N8—Mn1126.43 (15)C18—C19—C20120.9 (2)
C22—N8—Mn1112.66 (14)C18—C19—H19119.6
N1—C1—N2112.5 (2)C20—C19—H19119.6
N1—C1—H1123.7N7—C20—C19125.5 (2)
N2—C1—H1123.7N7—C20—C15115.78 (18)
C3—C2—N2106.4 (2)C19—C20—C15118.7 (2)
C3—C2—H2126.8O2—C21—N7130.6 (2)
N2—C2—H2126.8O2—C21—C22116.22 (19)
C2—C3—N1109.8 (2)N7—C21—C22113.13 (19)
C2—C3—H3125.1N8—C22—C23121.5 (2)
N1—C3—H3125.1N8—C22—C21118.04 (19)
N2—C4—H4A109.5C23—C22—C21120.44 (19)
N2—C4—H4B109.5C24—C23—C22119.4 (2)
H4A—C4—H4B109.5C24—C23—H23120.3
N2—C4—H4C109.5C22—C23—H23120.3
H4A—C4—H4C109.5C25—C24—C23119.0 (2)
H4B—C4—H4C109.5C25—C24—H24120.5
N3—C5—N4112.2 (2)C23—C24—H24120.5
N3—C5—H5123.9C24—C25—C26118.6 (2)
N4—C5—H5123.9C24—C25—H25120.7
C7—C6—N4106.0 (2)C26—C25—H25120.7
C7—C6—H6127.0N8—C26—C25122.6 (2)
N4—C6—H6127.0N8—C26—H26118.7
C6—C7—N3109.9 (2)C25—C26—H26118.7
C6—C7—H7125.0
N6—Mn1—N1—C1−92.7 (2)Mn1—N1—C3—C2−174.18 (17)
N7—Mn1—N1—C1−168.6 (2)C7—N3—C5—N40.2 (3)
N5—Mn1—N1—C1−18.7 (2)Mn1—N3—C5—N4−167.83 (14)
N8—Mn1—N1—C1117.1 (2)C6—N4—C5—N3−0.3 (3)
N3—Mn1—N1—C145.6 (3)C8—N4—C5—N3−179.6 (2)
N6—Mn1—N1—C380.7 (2)C5—N4—C6—C70.3 (3)
N7—Mn1—N1—C34.8 (2)C8—N4—C6—C7179.6 (2)
N5—Mn1—N1—C3154.7 (2)N4—C6—C7—N3−0.1 (3)
N8—Mn1—N1—C3−69.46 (19)C5—N3—C7—C60.0 (3)
N3—Mn1—N1—C3−140.97 (19)Mn1—N3—C7—C6166.84 (16)
N6—Mn1—N3—C534.70 (19)C13—N5—C9—C10−0.4 (3)
N7—Mn1—N3—C5112.38 (18)Mn1—N5—C9—C10165.25 (17)
N1—Mn1—N3—C5−102.6 (2)N5—C9—C10—C111.5 (3)
N5—Mn1—N3—C5−37.38 (18)C9—C10—C11—C12−1.0 (3)
N8—Mn1—N3—C5−175.39 (18)C10—C11—C12—C13−0.5 (3)
N6—Mn1—N3—C7−130.0 (2)C9—N5—C13—C12−1.2 (3)
N7—Mn1—N3—C7−52.4 (2)Mn1—N5—C13—C12−168.82 (16)
N1—Mn1—N3—C792.6 (2)C9—N5—C13—C14175.61 (19)
N5—Mn1—N3—C7157.9 (2)Mn1—N5—C13—C148.0 (2)
N8—Mn1—N3—C719.9 (2)C11—C12—C13—N51.6 (3)
N6—Mn1—N5—C9−166.23 (19)C11—C12—C13—C14−175.1 (2)
N7—Mn1—N5—C9−164.19 (16)C15—N6—C14—O11.1 (4)
N1—Mn1—N5—C994.73 (18)Mn1—N6—C14—O1−168.07 (19)
N8—Mn1—N5—C911.5 (2)C15—N6—C14—C13−174.87 (18)
N3—Mn1—N5—C9−59.78 (18)Mn1—N6—C14—C1316.0 (2)
N6—Mn1—N5—C130.09 (14)N5—C13—C14—O1167.57 (19)
N7—Mn1—N5—C132.1 (2)C12—C13—C14—O1−15.6 (3)
N1—Mn1—N5—C13−98.95 (15)N5—C13—C14—N6−15.9 (3)
N8—Mn1—N5—C13177.77 (13)C12—C13—C14—N6161.0 (2)
N3—Mn1—N5—C13106.54 (15)C14—N6—C15—C1612.7 (3)
N7—Mn1—N6—C14171.66 (18)Mn1—N6—C15—C16−177.88 (17)
N1—Mn1—N6—C1474.24 (17)C14—N6—C15—C20−170.9 (2)
N5—Mn1—N6—C14−9.40 (16)Mn1—N6—C15—C20−1.6 (2)
N8—Mn1—N6—C14173.83 (15)N6—C15—C16—C17177.1 (2)
N3—Mn1—N6—C14−86.90 (17)C20—C15—C16—C170.9 (3)
N7—Mn1—N6—C151.75 (14)C15—C16—C17—C18−0.1 (3)
N1—Mn1—N6—C15−95.67 (15)C16—C17—C18—C19−1.0 (4)
N5—Mn1—N6—C15−179.31 (16)C17—C18—C19—C201.2 (3)
N8—Mn1—N6—C153.9 (2)C21—N7—C20—C19−3.1 (3)
N3—Mn1—N6—C15103.19 (15)Mn1—N7—C20—C19178.62 (17)
N6—Mn1—N7—C21179.90 (17)C21—N7—C20—C15179.81 (19)
N1—Mn1—N7—C21−84.58 (16)Mn1—N7—C20—C151.5 (2)
N5—Mn1—N7—C21177.87 (15)C18—C19—C20—N7−177.3 (2)
N8—Mn1—N7—C211.03 (15)C18—C19—C20—C15−0.3 (3)
N3—Mn1—N7—C2179.48 (17)C16—C15—C20—N7176.57 (19)
N6—Mn1—N7—C20−1.75 (14)N6—C15—C20—N70.0 (3)
N1—Mn1—N7—C2093.76 (15)C16—C15—C20—C19−0.7 (3)
N5—Mn1—N7—C20−3.8 (2)N6—C15—C20—C19−177.28 (18)
N8—Mn1—N7—C20179.38 (15)C20—N7—C21—O2−5.9 (4)
N3—Mn1—N7—C20−102.17 (15)Mn1—N7—C21—O2172.31 (19)
N6—Mn1—N8—C26168.94 (17)C20—N7—C21—C22173.58 (18)
N7—Mn1—N8—C26171.1 (2)Mn1—N7—C21—C22−8.2 (2)
N1—Mn1—N8—C26−88.97 (19)C26—N8—C22—C23−1.3 (3)
N5—Mn1—N8—C26−6.6 (2)Mn1—N8—C22—C23163.93 (17)
N3—Mn1—N8—C2664.18 (19)C26—N8—C22—C21−179.3 (2)
N6—Mn1—N8—C225.1 (2)Mn1—N8—C22—C21−14.1 (2)
N7—Mn1—N8—C227.25 (14)O2—C21—C22—N8−165.29 (19)
N1—Mn1—N8—C22107.17 (15)N7—C21—C22—N815.1 (3)
N5—Mn1—N8—C22−170.47 (13)O2—C21—C22—C2316.7 (3)
N3—Mn1—N8—C22−99.68 (15)N7—C21—C22—C23−162.9 (2)
C3—N1—C1—N2−0.2 (3)N8—C22—C23—C24−0.4 (3)
Mn1—N1—C1—N2174.15 (16)C21—C22—C23—C24177.6 (2)
C2—N2—C1—N1−0.3 (3)C22—C23—C24—C251.9 (3)
C4—N2—C1—N1178.6 (2)C23—C24—C25—C26−1.8 (4)
C1—N2—C2—C30.6 (3)C22—N8—C26—C251.4 (3)
C4—N2—C2—C3−178.2 (2)Mn1—N8—C26—C25−161.57 (18)
N2—C2—C3—N1−0.8 (3)C24—C25—C26—N80.2 (4)
C1—N1—C3—C20.6 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2130).

References

  • Bruker (1998). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Havranek, M., Singh, A. & Sames, D. (1999). J. Am. Chem. Soc.121, 8965–8966.
  • Liang, L., Qu, Y.-Y., Yang, L. & Zhou, X.-G. (2007). Acta Cryst. E63, m1503–m1505.
  • Lin, J., Tu, C., Lin, H., Jiang, P., Ding, J. & Guo, Z. (2003). Inorg. Chem. Commun.6, 262–265.
  • Sheldrick, G. M. (2007). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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