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

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ISSN: 2056-9890

Bis(1-methyl-1H-imidazole-κN3)[N,N′-o-phenyl­enebis(pyridine-2-carbox­amido)-κ4N]manganese(II)

aChemistry Department, Faculty of Science, Tanta University, Tanta, Egypt, and bDepartment of Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Norman, OK 73019 USA
*Correspondence e-mail: grichteraddo@ou.edu

(Received 16 October 2008; accepted 8 December 2008; online 17 December 2008)

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[Liang, L., Qu, Y.-Y., Yang, L. & Zhou, X.-G. (2007). Acta Cryst. E63, m1503-m1505.]), Lin et al. (2003[Lin, J., Tu, C., Lin, H., Jiang, P., Ding, J. & Guo, Z. (2003). Inorg. Chem. Commun. 6, 262-265.]), and Havranek et al. (1999[Havranek, M., Singh, A. & Sames, D. (1999). J. Am. Chem. Soc. 121, 8965-8966.]).

[Scheme 1]

Experimental

Crystal data
  • [Mn(C18H12N4O2)(C4H6N2)2]

  • Mr = 535.47

  • Orthorhombic, P c a 21

  • 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[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.744, Tmax = 0.977

  • 8288 measured reflections

  • 3473 independent reflections

  • 3301 reflections with I > 2σ(I)

  • Rint = 0.022

Refinement
  • R[F2 > 2σ(F2)] = 0.025

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 989 Friedel pairs

  • Flack parameter: 0.046 (17)

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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)°.

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 35% probability level (H atoms omitted for clarity).
Bis(1-methyl-1H-imidazole-κN3)[N,N'-o- phenylenebis(pyridine-2-carboxamidato)-κ4N]manganese(II) top
Crystal data top
[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 top
Bruker APEX
diffractometer
3473 independent reflections
Radiation source: fine-focus sealed tube3301 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
h = 1617
Tmin = 0.744, Tmax = 0.977k = 127
8288 measured reflectionsl = 2213
Refinement top
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) = 0.062 w = 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 methodsAbsolute structure parameter: 0.046 (17)
Crystal data top
[Mn(C18H12N4O2)(C4H6N2)2]V = 2442.5 (9) Å3
Mr = 535.47Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 13.819 (3) ŵ = 0.58 mm1
b = 9.894 (2) ÅT = 100 K
c = 17.864 (4) Å0.54 × 0.35 × 0.04 mm
Data collection top
Bruker APEX
diffractometer
3473 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
3301 reflections with I > 2σ(I)
Tmin = 0.744, Tmax = 0.977Rint = 0.022
8288 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.062Δρmax = 0.33 e Å3
S = 1.02Δρmin = 0.19 e Å3
3473 reflectionsAbsolute structure: Flack (1983), 989 Friedel pairs
335 parametersAbsolute structure parameter: 0.046 (17)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H20.29020.02940.69350.034*
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*
H4C0.10350.07240.64650.040*
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)
H170.68000.00260.34470.025*
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) top
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, º) top
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—C192.7 (2)Mn1—N1—C3—C2174.18 (17)
N7—Mn1—N1—C1168.6 (2)C7—N3—C5—N40.2 (3)
N5—Mn1—N1—C118.7 (2)Mn1—N3—C5—N4167.83 (14)
N8—Mn1—N1—C1117.1 (2)C6—N4—C5—N30.3 (3)
N3—Mn1—N1—C145.6 (3)C8—N4—C5—N3179.6 (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—N30.1 (3)
N8—Mn1—N1—C369.46 (19)C5—N3—C7—C60.0 (3)
N3—Mn1—N1—C3140.97 (19)Mn1—N3—C7—C6166.84 (16)
N6—Mn1—N3—C534.70 (19)C13—N5—C9—C100.4 (3)
N7—Mn1—N3—C5112.38 (18)Mn1—N5—C9—C10165.25 (17)
N1—Mn1—N3—C5102.6 (2)N5—C9—C10—C111.5 (3)
N5—Mn1—N3—C537.38 (18)C9—C10—C11—C121.0 (3)
N8—Mn1—N3—C5175.39 (18)C10—C11—C12—C130.5 (3)
N6—Mn1—N3—C7130.0 (2)C9—N5—C13—C121.2 (3)
N7—Mn1—N3—C752.4 (2)Mn1—N5—C13—C12168.82 (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—C9166.23 (19)C11—C12—C13—C14175.1 (2)
N7—Mn1—N5—C9164.19 (16)C15—N6—C14—O11.1 (4)
N1—Mn1—N5—C994.73 (18)Mn1—N6—C14—O1168.07 (19)
N8—Mn1—N5—C911.5 (2)C15—N6—C14—C13174.87 (18)
N3—Mn1—N5—C959.78 (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—O115.6 (3)
N1—Mn1—N5—C1398.95 (15)N5—C13—C14—N615.9 (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—C16177.88 (17)
N1—Mn1—N6—C1474.24 (17)C14—N6—C15—C20170.9 (2)
N5—Mn1—N6—C149.40 (16)Mn1—N6—C15—C201.6 (2)
N8—Mn1—N6—C14173.83 (15)N6—C15—C16—C17177.1 (2)
N3—Mn1—N6—C1486.90 (17)C20—C15—C16—C170.9 (3)
N7—Mn1—N6—C151.75 (14)C15—C16—C17—C180.1 (3)
N1—Mn1—N6—C1595.67 (15)C16—C17—C18—C191.0 (4)
N5—Mn1—N6—C15179.31 (16)C17—C18—C19—C201.2 (3)
N8—Mn1—N6—C153.9 (2)C21—N7—C20—C193.1 (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—C2184.58 (16)Mn1—N7—C20—C151.5 (2)
N5—Mn1—N7—C21177.87 (15)C18—C19—C20—N7177.3 (2)
N8—Mn1—N7—C211.03 (15)C18—C19—C20—C150.3 (3)
N3—Mn1—N7—C2179.48 (17)C16—C15—C20—N7176.57 (19)
N6—Mn1—N7—C201.75 (14)N6—C15—C20—N70.0 (3)
N1—Mn1—N7—C2093.76 (15)C16—C15—C20—C190.7 (3)
N5—Mn1—N7—C203.8 (2)N6—C15—C20—C19177.28 (18)
N8—Mn1—N7—C20179.38 (15)C20—N7—C21—O25.9 (4)
N3—Mn1—N7—C20102.17 (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—C228.2 (2)
N1—Mn1—N8—C2688.97 (19)C26—N8—C22—C231.3 (3)
N5—Mn1—N8—C266.6 (2)Mn1—N8—C22—C23163.93 (17)
N3—Mn1—N8—C2664.18 (19)C26—N8—C22—C21179.3 (2)
N6—Mn1—N8—C225.1 (2)Mn1—N8—C22—C2114.1 (2)
N7—Mn1—N8—C227.25 (14)O2—C21—C22—N8165.29 (19)
N1—Mn1—N8—C22107.17 (15)N7—C21—C22—N815.1 (3)
N5—Mn1—N8—C22170.47 (13)O2—C21—C22—C2316.7 (3)
N3—Mn1—N8—C2299.68 (15)N7—C21—C22—C23162.9 (2)
C3—N1—C1—N20.2 (3)N8—C22—C23—C240.4 (3)
Mn1—N1—C1—N2174.15 (16)C21—C22—C23—C24177.6 (2)
C2—N2—C1—N10.3 (3)C22—C23—C24—C251.9 (3)
C4—N2—C1—N1178.6 (2)C23—C24—C25—C261.8 (4)
C1—N2—C2—C30.6 (3)C22—N8—C26—C251.4 (3)
C4—N2—C2—C3178.2 (2)Mn1—N8—C26—C25161.57 (18)
N2—C2—C3—N10.8 (3)C24—C25—C26—N80.2 (4)
C1—N1—C3—C20.6 (3)

Experimental details

Crystal data
Chemical formula[Mn(C18H12N4O2)(C4H6N2)2]
Mr535.47
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)100
a, b, c (Å)13.819 (3), 9.894 (2), 17.864 (4)
V3)2442.5 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.58
Crystal size (mm)0.54 × 0.35 × 0.04
Data collection
DiffractometerBruker APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.744, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections
8288, 3473, 3301
Rint0.022
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.062, 1.02
No. of reflections3473
No. of parameters335
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.19
Absolute structureFlack (1983), 989 Friedel pairs
Absolute structure parameter0.046 (17)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

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.

References

First citationBruker (1998). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHavranek, M., Singh, A. & Sames, D. (1999). J. Am. Chem. Soc. 121, 8965–8966.  Web of Science CSD CrossRef CAS Google Scholar
First citationLiang, L., Qu, Y.-Y., Yang, L. & Zhou, X.-G. (2007). Acta Cryst. E63, m1503–m1505.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLin, J., Tu, C., Lin, H., Jiang, P., Ding, J. & Guo, Z. (2003). Inorg. Chem. Commun. 6, 262–265.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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