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catena-Poly[[[bis­­(methanol-κO)bis­­(seleno­cyanato-κN)manganese(II)]-μ-1,2-bis­­(pyridin-4-yl)ethane-κ2N:N′] 1,2-bis­­(pyridin-4-yl)ethane monosolvate]

aInstitut für Anorganische Chemie, Christian-Albrechts-Universität Kiel, Max-Eyth-Strasse 2, 24118 Kiel, Germany
*Correspondence e-mail: swoehlert@ac.uni-kiel.de

(Received 13 March 2013; accepted 14 March 2013; online 20 March 2013)

The reaction of manganese seleno­cyanate with 1,2-bis­(pyridin-4-yl)ethane (bpa) leads to the title compound, {[Mn(NCSe)2(C12H12N2)(CH3OH)2]·C12H12N2}n. The MnII cation is coordinated by two N-bonded seleno­cyanate anions, two bpa ligands and two O-bonded methanol mol­ecules, within a slightly distorted octa­hedral geometry. The MnII cations and the non-coordinating N-donor ligands are located on centers of inversion while the coordinating N-donor co-ligands are located on a twofold rotation axis. In the crystal, the MnII cations are linked into chains along the c-axis direction by the bpa ligands. The chains are further connected via a non-coordinating bpa ligand into layers parallel to (3-10) via O—H⋯N hydrogen-bonding inter­actions.

Related literature

For background to this work and the structures of related compounds, see: Boeckmann & Näther (2010[Boeckmann, J. & Näther, C. (2010). Dalton Trans. 39, 11019-11026.], 2012[Boeckmann, J. & Näther, C. (2012). Polyhedron, 31, 587-595.]), Wöhlert et al. (2012[Wöhlert, S., Ruschewitz, U. & Näther, C. (2012). Cryst. Growth Des. 12, 2715-2718.]), Wöhlert & Näther (2012a[Wöhlert, S. & Näther, C. (2012a). Z. Anorg. Allg. Chem. 638, 2262-2272.],b[Wöhlert, S. & Näther, C. (2012b). Z. Naturforsch. Teil B, 67, 41-50.]).

[Scheme 1]

Experimental

Crystal data
  • [Mn(NCSe)2(C12H12N2)(CH4O)2]·C12H12N2

  • Mr = 697.46

  • Monoclinic, C 2/c

  • a = 19.184 (1) Å

  • b = 9.7854 (4) Å

  • c = 17.3468 (9) Å

  • β = 108.624 (4)°

  • V = 3085.9 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.82 mm−1

  • T = 293 K

  • 0.14 × 0.11 × 0.06 mm

Data collection
  • Stoe IPDS-2 diffractometer

  • Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2008[Stoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.493, Tmax = 0.748

  • 10827 measured reflections

  • 2998 independent reflections

  • 2556 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.094

  • S = 1.06

  • 2998 reflections

  • 179 parameters

  • H-atom parameters constrained

  • Δρmax = 0.56 e Å−3

  • Δρmin = −0.58 e Å−3

Table 1
Selected bond lengths (Å)

Mn1—N1 2.180 (3)
Mn1—O1 2.211 (2)
Mn1—N10 2.322 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1O1⋯N20 0.82 1.92 2.731 (3) 173

Data collection: X-AREA (Stoe & Cie, 2008[Stoe & Cie (2008). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 2011[Brandenburg, K. (2011). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: XCIF in SHELXTL.

Supporting information


Comment top

Recently, we have reported on the synthesis and characterization of thiocyanate coordination polymers with monodentate and bidentate neutral co-ligands like e.g. pyridine, pyridazine or 1,2-bis(pyridin-4-yl)ethylene (Boeckmann & Näther, 2010, 2012; Wöhlert & Näther, 2012a; Wöhlert & Näther, 2012b). Within this project we investigated the influence of the neutral co-ligand on the structural, thermal and magnetic properties of such compounds. In further work we also investigated the influence of the anionic ligand. In this context we have reported a new coordination polymer based on cobalt(II) selenocyanate and 1,2-bis(pyridin-4-yl)ethylene, in which the cobalt(II) cations are connected by the selenocyanato anions into chains that are further linked into layers by the neutral N-donor co-ligand (Wöhlert et al., 2012). In the present investigation we tried to prepare similar compounds with manganese(II) selenocyanate and 1,2-bis(pyridin-4-yl)ethane (bpa), which results in the formation of single-crystals of the title compound.

The asymmetric unit of the title compound [Mn(NCSe)2(C12H12N2)(CH3OH)2]n.nC12H12N2 solvate consists of a manganese(II) cation and one non-coordinating bpa ligand which are located on a center of inversion, one coordinating bpa ligand on a 2-fold rotation axis and one selenocyanate anion and one methanol molecule in general positions (Fig. 1). In the crystal structure each manganese(II) cation is coordinated by two terminal N-bonded selenocyanate anions, two O-bonded methanol molecules and two N-bonded bpa ligands within slightly distorted octahedra. The MnN4O2 distances ranges from 2.180 (3) Å to 2.322 (2) Å with angles around the manganese(II) cation between 88.87 (9) ° to 91.13 (9) ° and of 180 ° (Tab. 1). The manganese(II) cations are linked by the bpa ligands into chains which elongate in the direction of the crystallographic c-axis (Fig. 2). These chains are further linked into layers parallel to the (3 -1 0) plane by non-coordinated bpa molecules via O–H–N hydrogen bonding (Fig. 3).

Related literature top

For background to this work and the structures of related compounds, see: Boeckmann & Näther (2010, 2012), Wöhlert et al. (2012), Wöhlert & Näther (2012a,b).

Experimental top

MnCl2x2H2O, KNCSe and 1,2-bis(pyridin-4-yl)ethane were obtained from Alfa Aesar. All chemicals were used without further purification. 0.15 mmol (24 mg) MnCl2x2H2O and 0.2 mmol (28 mg) KNCSe were reacted with 0.6 mmol (109 mg) 1,2-bis(pyridin-4-yl)ethane in 1 ml methanol. Light-red single crystals of the title compound were obtained after one week.

Refinement top

The C—H H atoms were positions with idealized geometry (methyl H atoms allowed to rotate but not to tip) and were refined with Uiso(H) = 1.2 Ueq(C) (1.5 for methyl H atoms) using a riding model with C—H = 0.93 Å, C—H2 = 0.97 Å and C—H3 = 0.96 Å. The O—H H atom of the methanol molecule was located in difference map, its bond length was set to 0.82 Å and finally it was refined with Uiso(H) = 1.2 Ueq(O) using a riding model.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2008); cell refinement: X-AREA (Stoe & Cie, 2008); data reduction: X-AREA (Stoe & Cie, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011); software used to prepare material for publication: XCIF in SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level. [Symmetry codes: (i) -x,+1, -y+2, -z+1; (ii) -x+1, y, -z + 3/2; (iii) -x+1/2, -y+1/2, -z+1.]
[Figure 2] Fig. 2. The crystal structure of the title compound with view along the b-axis (black = manganese, blue = nitrogen, orange = selenium, red = oxygen, grey = carbon, white = hydrogen).
[Figure 3] Fig. 3. The crystal structure of the title compound with O—H···N hydrogen bonds shown as dashed lines (black = manganese, blue = nitrogen, orange = selenium, red = oxygen, grey = carbon, white = hydrogen).
catena-Poly[[[bis(methanol-κO)bis(selenocyanato-κN)manganese(II)]-µ-1,2-bis(pyridin-4-yl)ethane-κ2N:N'] 1,2-bis(pyridin-4-yl)ethane monosolvate] top
Crystal data top
[Mn(NCSe)2(C12H12N2)(CH4O)2]·C12H12N2F(000) = 1404
Mr = 697.46Dx = 1.501 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 10827 reflections
a = 19.184 (1) Åθ = 2.2–26.0°
b = 9.7854 (4) ŵ = 2.82 mm1
c = 17.3468 (9) ÅT = 293 K
β = 108.624 (4)°Block, light-red
V = 3085.9 (3) Å30.14 × 0.11 × 0.06 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
2998 independent reflections
Radiation source: fine-focus sealed tube2556 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scanθmax = 26.0°, θmin = 2.2°
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2008)
h = 2323
Tmin = 0.493, Tmax = 0.748k = 1210
10827 measured reflectionsl = 2121
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0346P)2 + 5.6439P]
where P = (Fo2 + 2Fc2)/3
2998 reflections(Δ/σ)max = 0.001
179 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.58 e Å3
Crystal data top
[Mn(NCSe)2(C12H12N2)(CH4O)2]·C12H12N2V = 3085.9 (3) Å3
Mr = 697.46Z = 4
Monoclinic, C2/cMo Kα radiation
a = 19.184 (1) ŵ = 2.82 mm1
b = 9.7854 (4) ÅT = 293 K
c = 17.3468 (9) Å0.14 × 0.11 × 0.06 mm
β = 108.624 (4)°
Data collection top
Stoe IPDS-2
diffractometer
2998 independent reflections
Absorption correction: numerical
(X-SHAPE and X-RED32; Stoe & Cie, 2008)
2556 reflections with I > 2σ(I)
Tmin = 0.493, Tmax = 0.748Rint = 0.032
10827 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.094H-atom parameters constrained
S = 1.06Δρmax = 0.56 e Å3
2998 reflectionsΔρmin = 0.58 e Å3
179 parameters
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.

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 > σ(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) top
xyzUiso*/Ueq
Mn10.50001.00000.50000.04285 (17)
N10.58695 (16)0.8976 (3)0.59516 (18)0.0613 (7)
C10.63537 (18)0.8574 (3)0.64832 (19)0.0490 (7)
Se10.71095 (2)0.79679 (6)0.72941 (2)0.07953 (18)
N100.51948 (13)1.1948 (3)0.58050 (15)0.0456 (6)
C100.48071 (18)1.3084 (3)0.55279 (19)0.0519 (7)
H100.44961.30920.49920.062*
C110.48422 (19)1.4238 (3)0.59895 (19)0.0538 (7)
H110.45581.49970.57650.065*
C120.52999 (17)1.4274 (3)0.67895 (18)0.0479 (7)
C130.57134 (18)1.3113 (3)0.70726 (19)0.0506 (7)
H130.60361.30870.76020.061*
C140.56489 (18)1.1998 (3)0.65745 (18)0.0503 (7)
H140.59361.12350.67820.060*
C150.5318 (2)1.5500 (3)0.7320 (2)0.0579 (8)
H15B0.52921.63240.70020.070*
H15A0.57821.55120.77610.070*
N200.34138 (14)0.6923 (3)0.51881 (16)0.0499 (6)
C200.31374 (17)0.6393 (3)0.57385 (19)0.0504 (7)
H200.32010.68760.62180.060*
C210.27652 (18)0.5175 (3)0.5634 (2)0.0525 (8)
H210.25920.48450.60420.063*
C220.26479 (16)0.4436 (3)0.49260 (19)0.0484 (7)
C230.29261 (19)0.4991 (4)0.4349 (2)0.0556 (8)
H230.28640.45370.38610.067*
C240.32931 (18)0.6210 (4)0.4504 (2)0.0556 (8)
H240.34700.65650.41050.067*
C250.22544 (19)0.3082 (3)0.4790 (2)0.0594 (8)
H25B0.20670.28980.42110.071*
H25A0.18380.31350.49910.071*
O10.41951 (12)0.9297 (2)0.55852 (13)0.0569 (6)
H1O10.39810.85710.54370.085*
C20.4253 (2)0.9473 (4)0.6411 (2)0.0733 (11)
H2A0.46740.89850.67470.110*
H2B0.38170.91260.65020.110*
H2C0.43051.04270.65460.110*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0432 (3)0.0442 (3)0.0405 (3)0.0021 (3)0.0125 (3)0.0006 (3)
N10.0589 (17)0.0628 (18)0.0552 (16)0.0070 (14)0.0083 (14)0.0008 (14)
C10.0547 (18)0.0482 (17)0.0464 (17)0.0017 (14)0.0194 (15)0.0048 (13)
Se10.0631 (2)0.1235 (4)0.0473 (2)0.0165 (2)0.01114 (17)0.0192 (2)
N100.0458 (13)0.0472 (14)0.0446 (13)0.0059 (11)0.0153 (11)0.0015 (11)
C100.0552 (18)0.0522 (18)0.0444 (16)0.0001 (15)0.0105 (14)0.0015 (14)
C110.0618 (19)0.0460 (18)0.0528 (18)0.0041 (15)0.0171 (15)0.0027 (14)
C120.0551 (17)0.0460 (17)0.0474 (16)0.0100 (14)0.0231 (14)0.0007 (13)
C130.0529 (17)0.0551 (19)0.0411 (15)0.0065 (15)0.0113 (13)0.0002 (14)
C140.0531 (17)0.0491 (17)0.0471 (17)0.0008 (14)0.0139 (14)0.0028 (14)
C150.078 (2)0.0452 (17)0.0534 (18)0.0115 (16)0.0252 (17)0.0031 (15)
N200.0517 (14)0.0441 (14)0.0524 (15)0.0061 (12)0.0144 (12)0.0033 (11)
C200.0539 (18)0.0471 (17)0.0509 (17)0.0018 (14)0.0179 (15)0.0029 (14)
C210.0586 (18)0.0501 (19)0.0542 (18)0.0050 (15)0.0258 (15)0.0060 (14)
C220.0445 (16)0.0423 (15)0.0574 (18)0.0046 (13)0.0150 (14)0.0021 (14)
C230.064 (2)0.0557 (18)0.0476 (17)0.0113 (17)0.0184 (15)0.0044 (15)
C240.0605 (19)0.058 (2)0.0504 (17)0.0138 (16)0.0208 (15)0.0050 (15)
C250.0547 (19)0.0495 (19)0.073 (2)0.0122 (15)0.0186 (17)0.0020 (16)
O10.0645 (14)0.0578 (13)0.0537 (12)0.0239 (11)0.0262 (11)0.0092 (11)
C20.088 (3)0.083 (3)0.056 (2)0.030 (2)0.032 (2)0.0117 (19)
Geometric parameters (Å, º) top
Mn1—N1i2.180 (3)C15—H15A0.9700
Mn1—N12.180 (3)N20—C241.331 (4)
Mn1—O1i2.211 (2)N20—C201.336 (4)
Mn1—O12.211 (2)C20—C211.372 (4)
Mn1—N10i2.322 (2)C20—H200.9300
Mn1—N102.322 (2)C21—C221.380 (5)
N1—C11.149 (4)C21—H210.9300
C1—Se11.769 (3)C22—C231.386 (4)
N10—C101.338 (4)C22—C251.506 (4)
N10—C141.342 (4)C23—C241.368 (5)
C10—C111.374 (4)C23—H230.9300
C10—H100.9300C24—H240.9300
C11—C121.386 (4)C25—C25iii1.509 (7)
C11—H110.9300C25—H25B0.9700
C12—C131.383 (5)C25—H25A0.9700
C12—C151.506 (4)O1—C21.412 (4)
C13—C141.372 (4)O1—H1O10.8200
C13—H130.9300C2—H2A0.9600
C14—H140.9300C2—H2B0.9600
C15—C15ii1.538 (7)C2—H2C0.9600
C15—H15B0.9700
N1i—Mn1—N1180.000 (1)C12—C15—H15B109.1
N1i—Mn1—O1i89.25 (10)C15ii—C15—H15B109.1
N1—Mn1—O1i90.75 (10)C12—C15—H15A109.1
N1i—Mn1—O190.75 (10)C15ii—C15—H15A109.1
N1—Mn1—O189.25 (10)H15B—C15—H15A107.9
O1i—Mn1—O1180.0C24—N20—C20116.0 (3)
N1i—Mn1—N10i89.13 (10)N20—C20—C21123.5 (3)
N1—Mn1—N10i90.87 (10)N20—C20—H20118.3
O1i—Mn1—N10i88.92 (8)C21—C20—H20118.3
O1—Mn1—N10i91.08 (8)C20—C21—C22120.2 (3)
N1i—Mn1—N1090.87 (10)C20—C21—H21119.9
N1—Mn1—N1089.13 (10)C22—C21—H21119.9
O1i—Mn1—N1091.08 (8)C21—C22—C23116.5 (3)
O1—Mn1—N1088.92 (8)C21—C22—C25122.1 (3)
N10i—Mn1—N10180.0C23—C22—C25121.4 (3)
C1—N1—Mn1172.7 (3)C24—C23—C22119.5 (3)
N1—C1—Se1179.0 (3)C24—C23—H23120.2
C10—N10—C14115.9 (3)C22—C23—H23120.2
C10—N10—Mn1120.1 (2)N20—C24—C23124.3 (3)
C14—N10—Mn1123.9 (2)N20—C24—H24117.8
N10—C10—C11123.7 (3)C23—C24—H24117.8
N10—C10—H10118.1C22—C25—C25iii112.6 (3)
C11—C10—H10118.1C22—C25—H25B109.1
C10—C11—C12120.1 (3)C25iii—C25—H25B109.1
C10—C11—H11119.9C22—C25—H25A109.1
C12—C11—H11119.9C25iii—C25—H25A109.1
C13—C12—C11116.3 (3)H25B—C25—H25A107.8
C13—C12—C15122.6 (3)C2—O1—Mn1126.0 (2)
C11—C12—C15121.1 (3)C2—O1—H1O1107.0
C14—C13—C12120.2 (3)Mn1—O1—H1O1118.7
C14—C13—H13119.9O1—C2—H2A109.5
C12—C13—H13119.9O1—C2—H2B109.5
N10—C14—C13123.7 (3)H2A—C2—H2B109.5
N10—C14—H14118.1O1—C2—H2C109.5
C13—C14—H14118.1H2A—C2—H2C109.5
C12—C15—C15ii112.4 (2)H2B—C2—H2C109.5
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y, z+3/2; (iii) x+1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N200.821.922.731 (3)173

Experimental details

Crystal data
Chemical formula[Mn(NCSe)2(C12H12N2)(CH4O)2]·C12H12N2
Mr697.46
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)19.184 (1), 9.7854 (4), 17.3468 (9)
β (°) 108.624 (4)
V3)3085.9 (3)
Z4
Radiation typeMo Kα
µ (mm1)2.82
Crystal size (mm)0.14 × 0.11 × 0.06
Data collection
DiffractometerStoe IPDS2
diffractometer
Absorption correctionNumerical
(X-SHAPE and X-RED32; Stoe & Cie, 2008)
Tmin, Tmax0.493, 0.748
No. of measured, independent and
observed [I > 2σ(I)] reflections
10827, 2998, 2556
Rint0.032
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.094, 1.06
No. of reflections2998
No. of parameters179
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.58

Computer programs: X-AREA (Stoe & Cie, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2011), XCIF in SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Mn1—N12.180 (3)Mn1—N102.322 (2)
Mn1—O12.211 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···N200.821.922.731 (3)172.6
 

Acknowledgements

We gratefully acknowledge financial support by the DFG (project No. NA 720/3–1) and the State of Schleswig–Holstein. We thank Professor Dr Wolfgang Bensch for access to his experimental facility.

References

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