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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 4| April 2011| Page m502
doi:10.1107/S1600536811010506

Bis(acetato-κ2O,O′)[2,6-bis­­(1H-pyrazol-3-yl-κN2)pyridine-κN]manganese(II)

Fan Yua* and Bao Lib

aSchool of Chemistry and Environmental Engineering, Jianghan University, Wuhan 430056, People's Republic of China, and bDepartment of Chemistry and Chemical Engineering, Huazhong University of Science and Technology, Wuhan 430074, People's Republic of China
*Correspondence e-mail: yufan0714@163.com

(Received 1 March 2011; accepted 21 March 2011; online 26 March 2011)

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]. π–π 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

For a related structure, see: Rich et al. (2010[Rich, J., Castillo, C. E., Romero, I., Rodríguez, M., Duboc, C. & Collomb, M.-N. (2010). Eur. J. Inorg. Chem. pp. 3658-3665.]).

[Scheme 1]

Experimental

Crystal data

  • [Mn(C2H3O2)2(C11H9N5)]

  • Mr = 384.26

  • Triclinic, [P \overline 1]

  • a = 8.2386 (16) Å

  • b = 9.4324 (19) Å

  • c = 11.081 (2) Å

  • α = 98.32 (3)°

  • β = 95.01 (3)°

  • γ = 106.11 (3)°

  • V = 811.2 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.85 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm
Data collection

  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.816, Tmax = 0.849

  • 5563 measured reflections

  • 3001 independent reflections

  • 2386 reflections with I > 2σ(I)

  • Rint = 0.030
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.117

  • S = 1.10

  • 3001 reflections

  • 226 parameters

  • H-atom parameters constrained

  • Δρmax = 0.51 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Selected bond lengths (Å)

Mn1—O1 2.480 (2)
Mn1—O2 2.192 (2)
Mn1—O3 2.596 (2)
Mn1—O4 2.160 (2)
Mn1—N2 2.262 (2)
Mn1—N3 2.235 (2)
Mn1—N4 2.270 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1B⋯O4i 0.86 1.91 2.751 (3) 165
N5—H5B⋯O2ii 0.86 1.85 2.712 (3) 180
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x+2, -y+2, -z+2.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); 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.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010506/hy2414sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010506/hy2414Isup2.hkl

checkCIF report


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)
Graphite monochromatorRint = 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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.10Δρmax = 0.51 e Å−3
3001 reflectionsΔρmin = −0.43 e Å−3
226 parameters
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, º) 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, º) 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.

Experimental details

Crystal data
Chemical formula[Mn(C2H3O2)2(C11H9N5)]
Mr384.26
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.2386 (16), 9.4324 (19), 11.081 (2)
α, β, γ (°)98.32 (3), 95.01 (3), 106.11 (3)
V (Å3)811.2 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.85
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.816, 0.849
No. of measured, independent and
observed [I > 2σ(I)] reflections		5563, 3001, 2386
Rint0.030
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.117, 1.10
No. of reflections3001
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.51, −0.43

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Selected bond lengths (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)
Hydrogen-bond geometry (Å, º) 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

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

References

First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationRich, J., Castillo, C. E., Romero, I., Rodríguez, M., Duboc, C. & Collomb, M.-N. (2010). Eur. J. Inorg. Chem. pp. 3658–3665.  Web of Science CSD CrossRef Google Scholar
 First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
 First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  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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COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 4| April 2011| Page m502
doi:10.1107/S1600536811010506
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