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Acta Cryst. (2011). E67, m502    [ doi:10.1107/S1600536811010506 ]

Bis(acetato-[kappa]2O,O')[2,6-bis(1H-pyrazol-3-yl-[kappa]N2)pyridine-[kappa]N]manganese(II)

F. Yu and B. Li

Abstract top

In the title complex, [Mn(CH3CO2)2(C11H9N5)], the MnII atom is coordinated by the pyridine N atom and two pyrazole N atoms from a 2,6-bis(pyrazol-3-yl)pyridine ligand and four O atoms from two bidentate acetate ligands. The complex molecules are linked by intermolecular N-H...O hydrogen bonds into a chain along [010]. [pi]-[pi] interactions between the pyridine rings and between the pyrazole rings [centroid-centroid distances = 3.772 (2) and 3.546 (2) Å] connect the chains.

Related literature top

For a related structure, see: Rich et al. (2010).

Experimental top

2,6-Bis(pyrazol-3-yl)pyridine (0.1 mmol) was dissolved in methanol (2.5 ml) with 0.2 mmol of trimethylamine. Mn(OAc)2 (0.2 mmol) in methanol (2.5 ml) was added into the resulting solution. After stirring at room temperature for 1 h, the resulting yellow solution was put into a tube layered with aether. Yellow crystals were obtained in three days.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.96 (CH3) and N—H = 0.86 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C, N).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound, showing the chain structures along the b axis. Dashed lines denote hydrogen bonds. H atoms have been omitted for clarity.
Bis(acetato-κ2O,O')[2,6-bis(1H-pyrazol-3-yl- κN2)pyridine-κN]manganese(II) top
Crystal data top
[Mn(C2H3O2)2(C11H9N5)]Z = 2
Mr = 384.26F(000) = 394
Triclinic, P1Dx = 1.573 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2386 (16) ÅCell parameters from 2386 reflections
b = 9.4324 (19) Åθ = 6.1–54.9°
c = 11.081 (2) ŵ = 0.85 mm−1
α = 98.32 (3)°T = 293 K
β = 95.01 (3)°Block, yellow
γ = 106.11 (3)°0.30 × 0.20 × 0.20 mm
V = 811.2 (3) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3001 independent reflections
Radiation source: rotation anode2386 reflections with I > 2σ(I)
graphiteRint = 0.030
ω scansθmax = 26.0°, θmin = 3.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −10→10
Tmin = 0.816, Tmax = 0.849k = −11→9
5563 measured reflectionsl = −13→13
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0565P)2]
where P = (Fo2 + 2Fc2)/3
3001 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.51 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
[Mn(C2H3O2)2(C11H9N5)]γ = 106.11 (3)°
Mr = 384.26V = 811.2 (3) Å3
Triclinic, P1Z = 2
a = 8.2386 (16) ÅMo Kα radiation
b = 9.4324 (19) ŵ = 0.85 mm−1
c = 11.081 (2) ÅT = 293 K
α = 98.32 (3)°0.30 × 0.20 × 0.20 mm
β = 95.01 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		3001 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		2386 reflections with I > 2σ(I)
Tmin = 0.816, Tmax = 0.849Rint = 0.030
5563 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.117Δρmax = 0.51 e Å−3
S = 1.10Δρmin = −0.43 e Å−3
3001 reflectionsAbsolute structure: ?
226 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.67466 (5)0.89985 (4)0.81715 (4)0.01323 (17)
N10.3285 (3)1.0204 (2)0.7643 (2)0.0155 (5)
H1B0.33271.06770.83750.019*
N20.4400 (3)0.9459 (2)0.7303 (2)0.0155 (5)
N30.6132 (3)0.7810 (2)0.6217 (2)0.0131 (5)
N40.8712 (3)0.7781 (2)0.7766 (2)0.0148 (5)
N51.0113 (3)0.7595 (3)0.8392 (2)0.0179 (5)
H5B1.05370.80290.91350.021*
C10.2104 (4)1.0115 (3)0.6700 (3)0.0187 (6)
H1A0.12171.05450.67320.022*
C20.2431 (4)0.9274 (3)0.5670 (3)0.0169 (6)
H2A0.18420.90250.48770.020*
C30.3877 (3)0.8887 (3)0.6116 (3)0.0156 (6)
C40.4818 (3)0.7946 (3)0.5476 (2)0.0135 (6)
C50.4382 (4)0.7223 (3)0.4265 (2)0.0181 (6)
H5A0.34620.73240.37710.022*
C60.5374 (4)0.6335 (3)0.3808 (3)0.0225 (7)
H6A0.51090.58240.29990.027*
C70.6738 (4)0.6213 (3)0.4548 (3)0.0204 (7)
H7A0.74130.56380.42440.025*
C80.7087 (4)0.6962 (3)0.5750 (2)0.0145 (6)
C90.8480 (4)0.6925 (3)0.6657 (3)0.0158 (6)
C100.9715 (4)0.6183 (4)0.6587 (3)0.0252 (7)
H10A0.98250.55080.59220.030*
C111.0740 (4)0.6645 (3)0.7698 (3)0.0213 (7)
H11A1.16960.63530.79260.026*
C121.0613 (4)1.3063 (3)0.8677 (3)0.0306 (8)
H12A1.09191.34070.79310.046*
H12B1.15681.28600.91000.046*
H12C1.02941.38230.91940.046*
C130.9129 (4)1.1649 (3)0.8373 (3)0.0166 (6)
O10.8498 (3)1.1097 (2)0.7299 (2)0.0253 (5)
O20.8561 (3)1.1034 (2)0.92644 (17)0.0196 (5)
C140.3975 (4)0.6485 (3)1.0567 (3)0.0228 (7)
H14A0.31700.55391.01970.034*
H14B0.33800.71421.09350.034*
H14C0.47660.63321.11880.034*
C150.4932 (4)0.7179 (3)0.9591 (3)0.0153 (6)
O30.4611 (3)0.6531 (2)0.85024 (18)0.0227 (5)
O40.6077 (3)0.8442 (2)0.99224 (18)0.0195 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0131 (3)0.0136 (3)0.0113 (2)0.00332 (17)0.00028 (18)−0.00105 (16)
N10.0176 (13)0.0184 (12)0.0118 (12)0.0079 (10)0.0042 (10)0.0006 (9)
N20.0136 (13)0.0139 (12)0.0192 (13)0.0045 (10)0.0024 (10)0.0029 (10)
N30.0139 (12)0.0139 (12)0.0114 (12)0.0035 (10)0.0023 (10)0.0024 (9)
N40.0146 (12)0.0180 (12)0.0110 (12)0.0050 (10)−0.0001 (10)0.0011 (9)
N50.0161 (13)0.0185 (13)0.0185 (13)0.0047 (10)−0.0002 (10)0.0037 (10)
C10.0177 (16)0.0223 (15)0.0179 (15)0.0082 (13)0.0028 (13)0.0052 (12)
C20.0176 (15)0.0212 (15)0.0110 (14)0.0052 (12)−0.0009 (12)0.0031 (11)
C30.0128 (14)0.0119 (14)0.0216 (16)0.0020 (11)0.0035 (12)0.0039 (11)
C40.0158 (15)0.0142 (14)0.0099 (14)0.0021 (11)0.0026 (12)0.0038 (11)
C50.0221 (16)0.0204 (15)0.0103 (14)0.0053 (13)−0.0028 (12)0.0031 (11)
C60.0296 (18)0.0196 (16)0.0186 (16)0.0085 (14)0.0045 (14)0.0012 (12)
C70.0250 (17)0.0215 (16)0.0172 (16)0.0113 (13)0.0050 (13)0.0010 (12)
C80.0176 (15)0.0153 (14)0.0106 (14)0.0047 (12)0.0021 (12)0.0026 (11)
C90.0164 (15)0.0170 (14)0.0143 (15)0.0049 (12)0.0041 (12)0.0022 (11)
C100.0300 (19)0.0326 (18)0.0166 (16)0.0195 (15)0.0017 (14)−0.0033 (13)
C110.0212 (17)0.0286 (17)0.0176 (16)0.0141 (14)0.0006 (13)0.0032 (13)
C120.0286 (19)0.0187 (16)0.039 (2)−0.0018 (14)0.0063 (16)0.0045 (14)
C130.0159 (15)0.0148 (14)0.0201 (16)0.0086 (12)0.0002 (13)0.0000 (12)
O10.0234 (12)0.0237 (12)0.0262 (12)0.0056 (10)0.0001 (10)0.0003 (9)
O20.0236 (11)0.0167 (10)0.0145 (11)0.0011 (9)0.0007 (9)0.0004 (8)
C140.0275 (17)0.0185 (15)0.0200 (16)0.0025 (13)0.0024 (14)0.0044 (12)
C150.0186 (15)0.0174 (14)0.0144 (15)0.0127 (12)0.0007 (12)0.0041 (11)
O30.0272 (12)0.0271 (12)0.0158 (11)0.0123 (10)0.0026 (9)0.0017 (9)
O40.0219 (11)0.0206 (11)0.0147 (11)0.0035 (9)0.0039 (9)0.0034 (8)
Geometric parameters (Å, °) top
Mn1—O12.480 (2)C5—C61.399 (4)
Mn1—O22.192 (2)C5—H5A0.9300
Mn1—O32.596 (2)C6—C71.373 (4)
Mn1—O42.160 (2)C6—H6A0.9300
Mn1—N22.262 (2)C7—C81.380 (4)
Mn1—N32.235 (2)C7—H7A0.9300
Mn1—N42.270 (2)C8—C91.469 (4)
N1—C11.341 (4)C9—C101.387 (4)
N1—N21.349 (3)C10—C111.370 (4)
N1—H1B0.8600C10—H10A0.9300
N2—C31.332 (4)C11—H11A0.9300
N3—C41.347 (3)C12—C131.510 (4)
N3—C81.353 (3)C12—H12A0.9600
N4—C91.336 (3)C12—H12B0.9600
N4—N51.361 (3)C12—H12C0.9600
N5—C111.338 (4)C13—O11.233 (3)
N5—H5B0.8600C13—O21.275 (3)
C1—C21.383 (4)C14—C151.512 (4)
C1—H1A0.9300C14—H14A0.9600
C2—C31.410 (4)C14—H14B0.9600
C2—H2A0.9300C14—H14C0.9600
C3—C41.478 (4)C15—O31.241 (3)
C4—C51.382 (4)C15—O41.278 (3)
O4—Mn1—O285.32 (8)N3—C4—C5122.6 (2)
O4—Mn1—N3135.59 (8)N3—C4—C3112.7 (2)
O2—Mn1—N3138.38 (8)C5—C4—C3124.6 (3)
O4—Mn1—N2103.71 (8)C4—C5—C6117.6 (3)
O2—Mn1—N2111.90 (8)C4—C5—H5A121.2
N3—Mn1—N271.44 (8)C6—C5—H5A121.2
O4—Mn1—N4103.09 (8)C7—C6—C5120.3 (3)
O2—Mn1—N495.79 (8)C7—C6—H6A119.8
N3—Mn1—N471.19 (8)C5—C6—H6A119.8
N2—Mn1—N4142.63 (8)C6—C7—C8118.8 (3)
O4—Mn1—O1140.27 (8)C6—C7—H7A120.6
O2—Mn1—O155.33 (7)C8—C7—H7A120.6
N3—Mn1—O184.13 (8)N3—C8—C7122.0 (3)
N2—Mn1—O188.11 (8)N3—C8—C9112.8 (2)
N4—Mn1—O187.66 (8)C7—C8—C9125.2 (3)
O4—Mn1—O354.13 (7)N4—C9—C10109.9 (3)
O2—Mn1—O3139.25 (7)N4—C9—C8117.9 (2)
N3—Mn1—O381.62 (7)C10—C9—C8132.1 (3)
N2—Mn1—O384.46 (7)C11—C10—C9106.1 (3)
N4—Mn1—O390.63 (7)C11—C10—H10A127.0
O1—Mn1—O3165.39 (6)C9—C10—H10A127.0
C1—N1—N2111.6 (2)N5—C11—C10107.3 (3)
C1—N1—H1B124.2N5—C11—H11A126.4
N2—N1—H1B124.2C10—C11—H11A126.4
C3—N2—N1104.9 (2)C13—C12—H12A109.5
C3—N2—Mn1117.16 (17)C13—C12—H12B109.5
N1—N2—Mn1137.93 (18)H12A—C12—H12B109.5
C4—N3—C8118.8 (2)C13—C12—H12C109.5
C4—N3—Mn1120.55 (17)H12A—C12—H12C109.5
C8—N3—Mn1120.66 (18)H12B—C12—H12C109.5
C9—N4—N5105.9 (2)O1—C13—O2121.1 (3)
C9—N4—Mn1117.09 (18)O1—C13—C12121.2 (3)
N5—N4—Mn1136.93 (17)O2—C13—C12117.8 (3)
C11—N5—N4110.9 (2)C13—O1—Mn185.49 (18)
C11—N5—H5B124.6C13—O2—Mn197.79 (17)
N4—N5—H5B124.6C15—C14—H14A109.5
N1—C1—C2108.3 (2)C15—C14—H14B109.5
N1—C1—H1A125.8H14A—C14—H14B109.5
C2—C1—H1A125.8C15—C14—H14C109.5
C1—C2—C3103.0 (3)H14A—C14—H14C109.5
C1—C2—H2A128.5H14B—C14—H14C109.5
C3—C2—H2A128.5O3—C15—O4121.3 (3)
N2—C3—C2112.1 (2)O3—C15—C14120.6 (3)
N2—C3—C4118.0 (2)O4—C15—C14118.1 (2)
C2—C3—C4129.8 (3)C15—O4—Mn1101.76 (17)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O4i0.861.912.751 (3)165
N5—H5B···O2ii0.861.852.712 (3)180
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+2, −y+2, −z+2.
Table 1
Selected geometric parameters (Å) top
Mn1—O12.480 (2)Mn1—N22.262 (2)
Mn1—O22.192 (2)Mn1—N32.235 (2)
Mn1—O32.596 (2)Mn1—N42.270 (2)
Mn1—O42.160 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O4i0.861.912.751 (3)165
N5—H5B···O2ii0.861.852.712 (3)180
Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+2, −y+2, −z+2.
Acknowledgements top

Jianghan University and Huazhong University of Science and Technology are thanked for financial support and a start-up grant.

references
References top

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

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Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.