Bis(acetyl­acetonato-κ2O,O′)(methanol-κO)(thio­cyanato-κN)manganese(III)

Meng, S.-M.; Xie, H.; Fan, Y.-Q.; Guo, Y.

doi:10.1107/S1600536808031589

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page m1363

doi:10.1107/S1600536808031589

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Bis(acetylacetonato-κ²O,O′)(methanol-κO)(thiocyanato-κN)manganese(III)

Shuang-Ming Meng,^a ^* Hai Xie,^a Yue-Qin Fan ^a and Yong Guo ^a

^aCollege of Chemistry and Chemical Engineering, Shanxi Datong University, Shanxi 037009, People's Republic of China
^*Correspondence e-mail: xhtgao@126.com

(Received 7 September 2008; accepted 30 September 2008; online 4 October 2008)

In the title complex, [Mn(C₅H₇O₂)₂(NCS)(CH₄O)], the Mn^III atom has a slightly distorted octahedral coordination formed by five O atoms and one N atom. The equatorial positions are occupied by four O atoms of two acetylacetonate ligands, while the axial positions are occupied by the N atom of the thiocyanate anion and the O atom of the methanol molecule. In the crystal structure, complex molecules are linked by an intermolecular O—H⋯S hydrogen bond, forming a chain running along [101].

Related literature

For the synthesis, see: Stults et al. (1975 ). For related structures, see: Stults et al. (1979 ); Swarnabala et al. (1994 ).

Experimental

Crystal data

[Mn(C₅H₇O₂)₂(NCS)(CH₄O)]
M_r = 343.27
Monoclinic, P 2₁ /n
a = 7.4795 (13) Å
b = 12.420 (2) Å
c = 17.586 (3) Å
β = 98.673 (4)°
V = 1614.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.96 mm⁻¹
T = 293 (2) K
0.21 × 0.19 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.824, T_max = 0.869
7925 measured reflections
2830 independent reflections
1276 reflections with I > 2σ(I)
R_int = 0.112

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.148
S = 0.91
2830 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯S1ⁱ	0.78 (7)	2.51 (6)	3.281 (4)	168 (7)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031589/is2333sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031589/is2333Isup2.hkl

checkCIF report

Comment top

Octahedral complexes of high-spin Mn^III are good examples for investigating the Jahn-Teller distortions, because their geometry are always distorted from the ideal octahedron to the distorted one by the axial ligands. Here, we report the structure of an octahedral Mn^III complex, whose synthesis has been reported early (Stults et al., 1975).

The molecular structure of the title complex is shown in Figure 1. The Mn^III atom is six coordinated by five O atoms and one N atom. The geometry can be described as a distorted octahedron. Four equational positions are occupied by four O atoms coming from two acetylacetonate ligands with the average Mn—O bond length 1.909 Å, which is in agreement well with the corresponding distance in [Mn(acac)₂(OH₂)₂]ClO₄].2H₂O. (Swarnabala et al., 1994). One SCN^- ion and one methanol molecule are coordinated to the Mn^III atom with trans positions, so that forming an octahedral geometry. The distance of Mn—O_methanol [2.289 (5) Å] is obviously longer than the bond lengths of Mn—O_{acetylacetonate}. The bond length of Mn—N_SCN is 2.187 (6) Å, which is also consistent with that found in [Mn(acac)₂(SCN)] (Stults et al., 1979). In the crystal structure, a molecular chain along the [101] direction is formed by an intermolecular H-bond between the O atom of the methanol molecule and the S atom of the SCN^- ion (Table 1).

Related literature top

For the synthesis, see: Stults et al. (1975). For related structures, see: Stults et al. (1979); Swarnabala et al. (1994). Please check changes.

Experimental top

The title complex was synthesized according to the literature method (Stults et al. 1975). The single crystals suitable for X-ray diffraction were grown from a methanol solution after the solvent was partial evaporated. Anal. Calcd for C₁₂H₁₈MnNO₅S: C 41.99, H 5.29, N 4.08; found: C 42.04, H 5.26, N, 4.11.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title complex with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted.

Bis(acetylacetonato-κ²O,O')(methanol-κO)(thiocyanato-κN)manganese(III) top

Crystal data top

[Mn(C₅H₇O₂)₂(NCS)(CH₄O)]	F(000) = 712
M_r = 343.27	D_x = 1.412 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 1347 reflections
a = 7.4795 (13) Å	θ = 2.8?–16.2°
b = 12.420 (2) Å	µ = 0.96 mm⁻¹
c = 17.586 (3) Å	T = 293 K
β = 98.673 (4)°	Block, brown
V = 1614.9 (5) Å³	0.21 × 0.19 × 0.15 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2830 independent reflections
Radiation source: fine-focus sealed tube	1276 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.112
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
T_min = 0.824, T_max = 0.869	k = −14→14
7925 measured reflections	l = −16→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.148	w = 1/[σ²(F_o²) + (0.0541P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max < 0.001
2830 reflections	Δρ_max = 0.33 e Å⁻³
189 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints

Crystal data top

[Mn(C₅H₇O₂)₂(NCS)(CH₄O)]	V = 1614.9 (5) Å³
M_r = 343.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4795 (13) Å	µ = 0.96 mm⁻¹
b = 12.420 (2) Å	T = 293 K
c = 17.586 (3) Å	0.21 × 0.19 × 0.15 mm
β = 98.673 (4)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2830 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1276 reflections with I > 2σ(I)
T_min = 0.824, T_max = 0.869	R_int = 0.112
7925 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	Δρ_max = 0.33 e Å⁻³
2830 reflections	Δρ_min = −0.33 e Å⁻³
189 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
Mn	0.86466 (12)	0.33696 (7)	0.64488 (5)	0.0398 (3)
S1	1.1860 (3)	0.34036 (15)	0.90976 (10)	0.0749 (7)
O1	1.0806 (5)	0.3054 (3)	0.6035 (2)	0.0504 (12)
O2	0.7813 (5)	0.1923 (3)	0.6275 (2)	0.0446 (11)
O3	0.6418 (5)	0.3674 (3)	0.6806 (2)	0.0458 (11)
O4	0.9347 (5)	0.4844 (3)	0.6515 (2)	0.0485 (12)
O5	0.7201 (7)	0.3709 (4)	0.5230 (3)	0.0682 (16)
H5A	0.701 (11)	0.325 (6)	0.491 (4)	0.102*
C1	1.0772 (9)	0.3201 (5)	0.8239 (4)	0.0455 (17)
C2	0.7403 (12)	0.4605 (6)	0.4764 (4)	0.100 (3)
H2A	0.7848	0.5205	0.5082	0.150*
H2B	0.6253	0.4788	0.4471	0.150*
H2C	0.8245	0.4437	0.4420	0.150*
C3	1.3234 (9)	0.2126 (6)	0.5642 (5)	0.084 (3)
H3A	1.3176	0.2455	0.5144	0.126*
H3B	1.3652	0.1398	0.5620	0.126*
H3C	1.4055	0.2524	0.6011	0.126*
C4	1.1395 (9)	0.2130 (6)	0.5877 (4)	0.0491 (17)
C5	1.0421 (9)	0.1195 (5)	0.5885 (4)	0.0537 (19)
H5	1.0977	0.0559	0.5768	0.064*
C6	0.8682 (10)	0.1122 (5)	0.6054 (3)	0.0472 (18)
C7	0.7645 (9)	0.0081 (4)	0.5966 (4)	0.061 (2)
H7A	0.7050	−0.0029	0.6407	0.091*
H7B	0.8463	−0.0504	0.5924	0.091*
H7C	0.6758	0.0110	0.5511	0.091*
C8	0.4019 (8)	0.4572 (5)	0.7255 (4)	0.058 (2)
H8A	0.3125	0.4324	0.6842	0.088*
H8B	0.3704	0.5280	0.7408	0.088*
H8C	0.4067	0.4089	0.7684	0.088*
C9	0.5827 (8)	0.4605 (5)	0.6990 (3)	0.0415 (16)
C10	0.6804 (9)	0.5539 (5)	0.6967 (4)	0.0531 (19)
H10	0.6281	0.6168	0.7118	0.064*
C11	0.8462 (10)	0.5633 (5)	0.6743 (4)	0.0510 (18)
C12	0.9380 (10)	0.6708 (5)	0.6760 (5)	0.092 (3)
H12A	1.0490	0.6684	0.7114	0.138*
H12B	0.8603	0.7250	0.6922	0.138*
H12C	0.9636	0.6880	0.6255	0.138*
N1	0.9996 (8)	0.3080 (5)	0.7624 (3)	0.0617 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn	0.0393 (6)	0.0339 (5)	0.0471 (6)	−0.0035 (5)	0.0093 (4)	−0.0032 (5)
S1	0.1019 (17)	0.0683 (13)	0.0490 (12)	−0.0013 (13)	−0.0060 (11)	0.0010 (11)
O1	0.043 (3)	0.046 (3)	0.065 (3)	−0.007 (2)	0.017 (2)	−0.012 (2)
O2	0.043 (3)	0.035 (2)	0.055 (3)	−0.003 (2)	0.005 (2)	−0.004 (2)
O3	0.041 (3)	0.041 (2)	0.057 (3)	−0.001 (2)	0.013 (2)	−0.003 (2)
O4	0.052 (3)	0.034 (2)	0.063 (3)	−0.003 (2)	0.016 (2)	−0.005 (2)
O5	0.090 (4)	0.069 (4)	0.043 (3)	−0.006 (3)	0.001 (3)	0.000 (3)
C1	0.041 (4)	0.042 (4)	0.056 (5)	−0.002 (3)	0.015 (4)	0.006 (4)
C2	0.135 (8)	0.097 (7)	0.061 (6)	−0.012 (6)	−0.003 (5)	0.024 (5)
C3	0.052 (5)	0.096 (6)	0.108 (7)	0.002 (4)	0.029 (5)	−0.041 (5)
C4	0.045 (5)	0.057 (4)	0.044 (4)	0.005 (4)	0.001 (3)	−0.013 (4)
C5	0.049 (5)	0.040 (4)	0.073 (5)	0.008 (4)	0.011 (4)	−0.010 (4)
C6	0.064 (5)	0.042 (4)	0.034 (4)	−0.002 (4)	0.001 (4)	−0.007 (3)
C7	0.076 (5)	0.038 (4)	0.066 (5)	−0.009 (4)	0.004 (4)	−0.007 (4)
C8	0.048 (5)	0.072 (5)	0.059 (5)	0.001 (4)	0.022 (4)	−0.014 (4)
C9	0.043 (4)	0.048 (4)	0.031 (4)	0.005 (3)	0.001 (3)	−0.006 (3)
C10	0.073 (6)	0.036 (4)	0.055 (5)	0.001 (4)	0.026 (4)	−0.011 (3)
C11	0.063 (5)	0.042 (4)	0.051 (5)	−0.010 (4)	0.019 (4)	−0.001 (4)
C12	0.109 (7)	0.039 (4)	0.140 (8)	−0.012 (5)	0.061 (6)	−0.015 (5)
N1	0.062 (4)	0.067 (4)	0.054 (4)	−0.015 (3)	0.001 (3)	0.003 (3)

Geometric parameters (Å, º) top

Mn—O4	1.903 (4)	C3—H3C	0.9600
Mn—O2	1.911 (4)	C4—C5	1.372 (8)
Mn—O3	1.906 (4)	C5—C6	1.380 (8)
Mn—O1	1.910 (4)	C5—H5	0.9300
Mn—N1	2.189 (6)	C6—C7	1.505 (8)
Mn—O5	2.289 (5)	C7—H7A	0.9600
S1—C1	1.623 (8)	C7—H7B	0.9600
O1—C4	1.275 (6)	C7—H7C	0.9600
O2—C6	1.280 (7)	C8—C9	1.495 (8)
O3—C9	1.296 (6)	C8—H8A	0.9600
O4—C11	1.281 (7)	C8—H8B	0.9600
O5—C2	1.405 (8)	C8—H8C	0.9600
O5—H5A	0.80 (7)	C9—C10	1.375 (8)
C1—N1	1.157 (7)	C10—C11	1.361 (8)
C2—H2A	0.9600	C10—H10	0.9300
C2—H2B	0.9600	C11—C12	1.501 (8)
C2—H2C	0.9600	C12—H12A	0.9600
C3—C4	1.494 (8)	C12—H12B	0.9600
C3—H3A	0.9600	C12—H12C	0.9600
C3—H3B	0.9600

O4—Mn—O2	173.85 (19)	O1—C4—C5	123.9 (6)
O4—Mn—O3	92.02 (17)	O1—C4—C3	115.2 (6)
O2—Mn—O3	87.66 (16)	C5—C4—C3	120.8 (6)
O4—Mn—O1	88.83 (17)	C4—C5—C6	125.2 (6)
O2—Mn—O1	91.17 (17)	C4—C5—H5	117.4
O3—Mn—O1	176.83 (18)	C6—C5—H5	117.4
O4—Mn—N1	91.0 (2)	O2—C6—C5	123.6 (6)
O2—Mn—N1	95.16 (19)	O2—C6—C7	114.9 (6)
O3—Mn—N1	91.32 (19)	C5—C6—C7	121.5 (6)
O1—Mn—N1	91.7 (2)	C6—C7—H7A	109.5
O4—Mn—O5	88.09 (17)	C6—C7—H7B	109.5
O2—Mn—O5	85.76 (18)	H7A—C7—H7B	109.5
O3—Mn—O5	87.65 (18)	C6—C7—H7C	109.5
O1—Mn—O5	89.33 (18)	H7A—C7—H7C	109.5
N1—Mn—O5	178.6 (2)	H7B—C7—H7C	109.5
C4—O1—Mn	127.4 (4)	C9—C8—H8A	109.5
C6—O2—Mn	127.6 (4)	C9—C8—H8B	109.5
C9—O3—Mn	127.4 (4)	H8A—C8—H8B	109.5
C11—O4—Mn	127.2 (4)	C9—C8—H8C	109.5
C2—O5—Mn	128.0 (4)	H8A—C8—H8C	109.5
C2—O5—H5A	100 (6)	H8B—C8—H8C	109.5
Mn—O5—H5A	123 (6)	O3—C9—C10	122.8 (6)
N1—C1—S1	178.5 (7)	O3—C9—C8	114.3 (5)
O5—C2—H2A	109.5	C10—C9—C8	122.9 (6)
H5A—C2—H2A	136.0	C11—C10—C9	126.3 (6)
O5—C2—H2B	109.5	C11—C10—H10	116.8
H5A—C2—H2B	98.6	C9—C10—H10	116.8
H2A—C2—H2B	109.5	O4—C11—C10	124.2 (6)
O5—C2—H2C	109.5	O4—C11—C12	115.5 (6)
H5A—C2—H2C	91.3	C10—C11—C12	120.3 (6)
H2A—C2—H2C	109.5	C11—C12—H12A	109.5
H2B—C2—H2C	109.5	C11—C12—H12B	109.5
C4—C3—H3A	109.5	H12A—C12—H12B	109.5
C4—C3—H3B	109.5	C11—C12—H12C	109.5
H3A—C3—H3B	109.5	H12A—C12—H12C	109.5
C4—C3—H3C	109.5	H12B—C12—H12C	109.5
H3A—C3—H3C	109.5	C1—N1—Mn	162.9 (6)
H3B—C3—H3C	109.5

O4—Mn—O1—C4	174.8 (5)	Mn—O1—C4—C5	9.1 (9)
O2—Mn—O1—C4	−11.4 (5)	Mn—O1—C4—C3	−173.5 (4)
N1—Mn—O1—C4	83.8 (5)	O1—C4—C5—C6	0.8 (11)
O5—Mn—O1—C4	−97.1 (5)	C3—C4—C5—C6	−176.4 (6)
O3—Mn—O2—C6	−175.2 (5)	Mn—O2—C6—C5	−1.7 (8)
O1—Mn—O2—C6	7.7 (5)	Mn—O2—C6—C7	−179.7 (4)
N1—Mn—O2—C6	−84.2 (5)	C4—C5—C6—O2	−4.7 (10)
O5—Mn—O2—C6	96.9 (5)	C4—C5—C6—C7	173.2 (6)
O4—Mn—O3—C9	0.7 (5)	Mn—O3—C9—C10	−1.7 (8)
O2—Mn—O3—C9	−173.2 (5)	Mn—O3—C9—C8	−179.9 (3)
N1—Mn—O3—C9	91.7 (5)	O3—C9—C10—C11	1.3 (10)
O5—Mn—O3—C9	−87.3 (5)	C8—C9—C10—C11	179.4 (6)
O3—Mn—O4—C11	0.8 (5)	Mn—O4—C11—C10	−1.3 (9)
O1—Mn—O4—C11	177.8 (5)	Mn—O4—C11—C12	177.7 (4)
N1—Mn—O4—C11	−90.5 (5)	C9—C10—C11—O4	0.3 (11)
O5—Mn—O4—C11	88.4 (5)	C9—C10—C11—C12	−178.7 (6)
O4—Mn—O5—C2	15.3 (5)	O4—Mn—N1—C1	5.2 (18)
O3—Mn—O5—C2	107.5 (5)	O3—Mn—N1—C1	−86.9 (18)
O1—Mn—O5—C2	−73.5 (5)	O1—Mn—N1—C1	94.0 (18)
O2—Mn—O5—C2	−164.7 (5)	O2—Mn—N1—C1	−174.6 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···S1ⁱ	0.78 (7)	2.51 (6)	3.281 (4)	168 (7)

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Mn(C₅H₇O₂)₂(NCS)(CH₄O)]
M_r	343.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.4795 (13), 12.420 (2), 17.586 (3)
β (°)	98.673 (4)
V (Å³)	1614.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.96
Crystal size (mm)	0.21 × 0.19 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.824, 0.869
No. of measured, independent and observed [I > 2σ(I)] reflections	7925, 2830, 1276
R_int	0.112
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.148, 0.91
No. of reflections	2830
No. of parameters	189
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.33

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···S1ⁱ	0.78 (7)	2.51 (6)	3.281 (4)	168 (7)

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

References

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Volume 64| Part 11| November 2008| Page m1363

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