Bis{μ-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato}bis­[(thio­cyanato)manganese(III)]

Wang, S.-B.; Tang, K.; Yang, B.-H.; Li, S.

doi:10.1107/S1600536808003577

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page m543

doi:10.1107/S1600536808003577

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Bis{μ-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}bis[(thiocyanato)manganese(III)]

Shou-Bin Wang,^a ^* Kun Tang,^b Bao-Hua Yang ^b and Sheng Li ^b

^aCollege of Chemistry and Chemical Engineering, Henan University, Kaifeng 475003, People's Republic of China, and ^bCollege of Medicine, Henan University, Kaifeng 475003, People's Republic of China
^*Correspondence e-mail: wangsb6688@sina.com

(Received 7 January 2008; accepted 1 February 2008; online 14 March 2008)

The reported structure is a monoclinic polymorph of the title compound, [Mn₂(C₁₆H₁₄N₂O₂)₂(NCS)₂], which has been characterized previously in an orthorhombic form. Each Mn^III atom is chelated by a tetradentate 2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolate ligand and by the N atom of a thiocyanate anion, in a square-pyramidal arrangement. The complexes form centrosymmetric dimers, with an Mn—O contact of 2.557 (3) Å trans to each thiocyanate anion, completing a distorted octahedral coordination geometry.

Related literature

For the orthorhombic polymorph, see: Mikuriya et al. (1992 ); Li et al. (1997 ).

Experimental

Crystal data

[Mn₂(C₁₆H₁₄N₂O₂)₂(NCS)₂]
M_r = 758.62
Monoclinic, P 2₁ /n
a = 9.0026 (10) Å
b = 14.0629 (16) Å
c = 14.9884 (17) Å
β = 106.848 (1)°
V = 1816.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.85 mm⁻¹
T = 293 (2) K
0.43 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.710, T_max = 0.834
13254 measured reflections
3296 independent reflections
2627 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.231
S = 1.00
3296 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 1.47 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Mn1—O1	1.874 (3)
Mn1—O2	1.902 (3)
Mn1—N1	1.979 (4)
Mn1—N2	1.990 (5)
Mn1—N3	2.181 (5)
Mn1—O2ⁱ	2.557 (3)

O1—Mn1—O2	94.95 (14)
O1—Mn1—N1	92.1 (2)
O1—Mn1—N2	170.90 (17)
O1—Mn1—N3	93.94 (18)
O1—Mn1—O2ⁱ	88.62 (15)
O2—Mn1—N1	165.40 (19)
O2—Mn1—N2	89.51 (17)
O2—Mn1—N3	96.85 (17)
O2—Mn1—O2ⁱ	80.14 (14)
N1—Mn1—N2	81.9 (2)
N1—Mn1—N3	95.4 (2)
N1—Mn1—O2ⁱ	87.29 (16)
N2—Mn1—N3	93.4 (2)
N2—Mn1—O2ⁱ	84.35 (17)
N3—Mn1—O2ⁱ	176.24 (17)
Symmetry code: (i) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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/S1600536808003577/bi2278sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003577/bi2278Isup2.hkl

checkCIF report

Comment top

As shown in Fig. 1, the Mn atom is chelated by two N and two O atoms of the N,N'-ethylenebis(salicylideneamine) ligand and by the N atom of the thiocyanate anion in the apical site. The Mn—N and Mn—O bond lengths are in the range of 1.979 (4)–2.181 (5) and 1.874 (3)–1.902 (3) %A, respectively (Table 1).

Related literature top

For the orthorhombic polymorph, see: Mikuriya et al. (1992); Li et al. (1997).

Experimental top

A mixture of manganese(III) acetate (1 mmol) and N,N'-bis(2-hydroxybenzyl)ethylenediamine (1 mmol) in 20 ml me thanol was refluxed for several hours. The solution was then cooled and filtered, and the filtrate was left to evaporate at room temperature. Pink blocks of the title compound were obtained after 2 days with a yield of 12%. Elemental analysis calculated: C 53.72, H 3.67, N 5.49%; found: C 53.78, H 3.69, N 5.54%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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. Asymmetric unit drawn with 30% probability displacement ellipsoids for the non-H atoms.

Bis{µ-2,2'-[ethane-1,2- diylbis(nitrilomethylidyne)]diphenolato}bis[(thiocyanato)manganese(III)] top

Crystal data top

[Mn₂(C₁₆H₁₄N₂O₂)₂(NCS)₂]	F(000) = 776
M_r = 758.62	D_x = 1.387 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4497 reflections
a = 9.0026 (10) Å	θ = 2.4–24.4°
b = 14.0629 (16) Å	µ = 0.86 mm⁻¹
c = 14.9884 (17) Å	T = 293 K
β = 106.848 (1)°	Block, pink
V = 1816.1 (4) Å³	0.43 × 0.28 × 0.22 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	3296 independent reflections
Radiation source: fine-focus sealed tube	2627 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
T_min = 0.710, T_max = 0.834	k = −16→16
13254 measured reflections	l = −18→17

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.231	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.147P)² + 2.2875P] where P = (F_o² + 2F_c²)/3
3296 reflections	(Δ/σ)_max = 0.013
193 parameters	Δρ_max = 1.47 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Mn₂(C₁₆H₁₄N₂O₂)₂(NCS)₂]	V = 1816.1 (4) Å³
M_r = 758.62	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.0026 (10) Å	µ = 0.86 mm⁻¹
b = 14.0629 (16) Å	T = 293 K
c = 14.9884 (17) Å	0.43 × 0.28 × 0.22 mm
β = 106.848 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3296 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2627 reflections with I > 2σ(I)
T_min = 0.710, T_max = 0.834	R_int = 0.023
13254 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.231	H-atom parameters constrained
S = 1.00	Δρ_max = 1.47 e Å⁻³
3296 reflections	Δρ_min = −0.33 e Å⁻³
193 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

	x	y	z	U_iso*/U_eq
Mn1	0.64485 (8)	0.01038 (5)	0.10349 (5)	0.0575 (3)
C1	0.8655 (4)	0.1314 (2)	0.0466 (3)	0.0705 (14)
C2	0.9625 (5)	0.1411 (3)	−0.0101 (3)	0.093 (2)
H2	0.9766	0.0902	−0.0465	0.112*
C3	1.0384 (5)	0.2267 (4)	−0.0124 (4)	0.124 (3)
H3	1.1033	0.2332	−0.0503	0.148*
C4	1.0173 (6)	0.3027 (3)	0.0420 (4)	0.146 (4)
H4	1.0681	0.3600	0.0404	0.175*
C5	0.9204 (6)	0.2931 (3)	0.0987 (4)	0.128 (3)
H5	0.9063	0.3439	0.1351	0.153*
C6	0.8445 (5)	0.2074 (3)	0.1010 (3)	0.0848 (17)
C7	0.9436 (7)	−0.0871 (3)	0.2500 (4)	0.0640 (12)
C8	0.7500 (9)	0.2027 (5)	0.1635 (4)	0.098 (2)
H8	0.7466	0.2568	0.1986	0.117*
C9	0.5841 (12)	0.1325 (5)	0.2457 (5)	0.117 (3)
H9A	0.5629	0.1977	0.2592	0.140*
H9B	0.6451	0.1027	0.3030	0.140*
C10	0.4299 (12)	0.0775 (6)	0.2049 (7)	0.125 (3)
H10A	0.3826	0.0616	0.2535	0.150*
H10B	0.3571	0.1147	0.1574	0.150*
C11	0.4148 (7)	−0.0916 (5)	0.1681 (4)	0.0801 (16)
H11	0.3420	−0.0952	0.2011	0.096*
C12	0.4489 (4)	−0.1778 (2)	0.1251 (2)	0.0686 (13)
C13	0.4001 (5)	−0.2635 (3)	0.1534 (3)	0.0921 (19)
H13	0.3496	−0.2641	0.1994	0.110*
C14	0.4266 (6)	−0.3482 (2)	0.1127 (3)	0.106 (2)
H14	0.3939	−0.4055	0.1316	0.128*
C15	0.5020 (5)	−0.34726 (18)	0.0439 (3)	0.0937 (19)
H15	0.5197	−0.4040	0.0167	0.112*
C16	0.5508 (4)	−0.2616 (2)	0.0156 (2)	0.0723 (14)
H16	0.6013	−0.2610	−0.0304	0.087*
C17	0.5243 (4)	−0.17685 (18)	0.0563 (2)	0.0592 (11)
N1	0.6693 (7)	0.1302 (3)	0.1756 (3)	0.0799 (13)
N2	0.4777 (6)	−0.0108 (3)	0.1639 (3)	0.0737 (12)
N3	0.8165 (6)	−0.0691 (4)	0.2100 (4)	0.0823 (13)
O1	0.7880 (4)	0.0494 (3)	0.0418 (3)	0.0692 (9)
O2	0.5682 (4)	−0.0941 (2)	0.0227 (2)	0.0574 (8)
S1	1.11942 (18)	−0.11754 (13)	0.30794 (13)	0.0894 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0669 (5)	0.0504 (5)	0.0598 (5)	0.0061 (3)	0.0259 (4)	−0.0011 (3)
C1	0.057 (3)	0.066 (3)	0.080 (3)	−0.005 (2)	0.005 (2)	0.012 (3)
C2	0.061 (3)	0.089 (4)	0.127 (6)	−0.007 (3)	0.023 (3)	0.022 (4)
C3	0.076 (4)	0.120 (7)	0.159 (8)	−0.037 (4)	0.010 (4)	0.042 (6)
C4	0.117 (7)	0.112 (7)	0.162 (9)	−0.061 (6)	−0.034 (6)	0.028 (6)
C5	0.133 (7)	0.085 (5)	0.123 (6)	−0.041 (5)	−0.029 (5)	0.002 (4)
C6	0.091 (4)	0.068 (3)	0.075 (4)	−0.012 (3)	−0.009 (3)	−0.001 (3)
C7	0.080 (3)	0.051 (3)	0.066 (3)	0.006 (2)	0.029 (3)	0.010 (2)
C8	0.130 (6)	0.064 (4)	0.071 (4)	0.009 (4)	−0.015 (4)	−0.016 (3)
C9	0.190 (9)	0.082 (5)	0.090 (5)	0.030 (5)	0.058 (5)	−0.015 (4)
C10	0.169 (8)	0.110 (6)	0.130 (6)	0.039 (6)	0.098 (6)	−0.011 (5)
C11	0.079 (3)	0.105 (5)	0.067 (3)	0.013 (3)	0.037 (3)	0.023 (3)
C12	0.061 (3)	0.079 (3)	0.066 (3)	0.000 (2)	0.018 (2)	0.020 (3)
C13	0.090 (4)	0.102 (5)	0.084 (4)	−0.019 (4)	0.025 (3)	0.030 (4)
C14	0.111 (5)	0.073 (4)	0.124 (6)	−0.021 (4)	0.017 (5)	0.035 (4)
C15	0.090 (4)	0.058 (3)	0.126 (6)	0.000 (3)	0.021 (4)	0.010 (3)
C16	0.070 (3)	0.053 (3)	0.093 (4)	0.003 (2)	0.021 (3)	0.005 (2)
C17	0.055 (2)	0.054 (2)	0.068 (3)	0.001 (2)	0.017 (2)	0.006 (2)
N1	0.114 (4)	0.061 (3)	0.061 (3)	0.016 (3)	0.020 (2)	−0.006 (2)
N2	0.085 (3)	0.079 (3)	0.070 (3)	0.015 (2)	0.043 (2)	0.006 (2)
N3	0.085 (3)	0.078 (3)	0.082 (3)	0.016 (3)	0.020 (3)	0.011 (2)
O1	0.069 (2)	0.060 (2)	0.084 (2)	−0.0027 (16)	0.0313 (18)	−0.0004 (17)
O2	0.0661 (19)	0.0491 (16)	0.0641 (18)	0.0026 (14)	0.0302 (15)	0.0026 (14)
S1	0.0697 (9)	0.0979 (12)	0.1010 (12)	0.0079 (8)	0.0256 (8)	0.0270 (9)

Geometric parameters (Å, º) top

Mn1—O1	1.874 (3)	C9—N1	1.469 (9)
Mn1—O2	1.902 (3)	C9—C10	1.552 (13)
Mn1—N1	1.979 (4)	C9—H9A	0.970
Mn1—N2	1.990 (5)	C9—H9B	0.970
Mn1—N3	2.181 (5)	C10—N2	1.503 (8)
Mn1—O2ⁱ	2.557 (3)	C10—H10A	0.970
C1—O1	1.339 (4)	C10—H10B	0.970
C1—C2	1.390	C11—N2	1.280 (8)
C1—C6	1.390	C11—C12	1.447 (7)
C2—C3	1.390	C11—H11	0.930
C2—H2	0.930	C12—C13	1.390
C3—C4	1.390	C12—C17	1.390
C3—H3	0.930	C13—C14	1.390
C4—C5	1.390	C13—H13	0.930
C4—H4	0.930	C14—C15	1.390
C5—C6	1.390	C14—H14	0.930
C5—H5	0.930	C15—C16	1.390
C6—C8	1.439 (9)	C15—H15	0.930
C7—N3	1.155 (7)	C16—C17	1.390
C7—S1	1.627 (6)	C16—H16	0.930
C8—N1	1.295 (9)	C17—O2	1.371 (4)
C8—H8	0.930

O1—Mn1—O2	94.95 (14)	N1—C9—H9B	110.2
O1—Mn1—N1	92.1 (2)	C10—C9—H9B	110.2
O1—Mn1—N2	170.90 (17)	H9A—C9—H9B	108.5
O1—Mn1—N3	93.94 (18)	N2—C10—C9	104.1 (6)
O1—Mn1—O2ⁱ	88.62 (15)	N2—C10—H10A	110.9
O2—Mn1—N1	165.40 (19)	C9—C10—H10A	110.9
O2—Mn1—N2	89.51 (17)	N2—C10—H10B	110.9
O2—Mn1—N3	96.85 (17)	C9—C10—H10B	110.9
O2—Mn1—O2ⁱ	80.14 (14)	H10A—C10—H10B	109.0
N1—Mn1—N2	81.9 (2)	N2—C11—C12	124.6 (5)
N1—Mn1—N3	95.4 (2)	N2—C11—H11	117.7
N1—Mn1—O2ⁱ	87.29 (16)	C12—C11—H11	117.7
N2—Mn1—N3	93.4 (2)	C13—C12—C17	120.0
N2—Mn1—O2ⁱ	84.35 (17)	C13—C12—C11	117.6 (3)
N3—Mn1—O2ⁱ	176.24 (17)	C17—C12—C11	122.3 (3)
O1—C1—C2	117.4 (3)	C12—C13—C14	120.0
O1—C1—C6	122.4 (3)	C12—C13—H13	120.0
C2—C1—C6	120.0	C14—C13—H13	120.0
C3—C2—C1	120.0	C13—C14—C15	120.0
C3—C2—H2	120.0	C13—C14—H14	120.0
C1—C2—H2	120.0	C15—C14—H14	120.0
C2—C3—C4	120.0	C14—C15—C16	120.0
C2—C3—H3	120.0	C14—C15—H15	120.0
C4—C3—H3	120.0	C16—C15—H15	120.0
C5—C4—C3	120.0	C17—C16—C15	120.0
C5—C4—H4	120.0	C17—C16—H16	120.0
C3—C4—H4	120.0	C15—C16—H16	120.0
C4—C5—C6	120.0	O2—C17—C16	117.5 (2)
C4—C5—H5	120.0	O2—C17—C12	122.4 (2)
C6—C5—H5	120.0	C16—C17—C12	120.0
C5—C6—C1	120.0	C8—N1—C9	120.8 (6)
C5—C6—C8	116.3 (4)	C8—N1—Mn1	124.9 (4)
C1—C6—C8	123.6 (4)	C9—N1—Mn1	114.2 (4)
N3—C7—S1	177.1 (5)	C11—N2—C10	122.0 (6)
N1—C8—C6	126.1 (5)	C11—N2—Mn1	124.0 (4)
N1—C8—H8	117.0	C10—N2—Mn1	114.0 (5)
C6—C8—H8	117.0	C7—N3—Mn1	151.3 (5)
N1—C9—C10	107.5 (6)	C1—O1—Mn1	130.4 (3)
N1—C9—H9A	110.2	C17—O2—Mn1	120.8 (2)
C10—C9—H9A	110.2

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Mn₂(C₁₆H₁₄N₂O₂)₂(NCS)₂]
M_r	758.62
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.0026 (10), 14.0629 (16), 14.9884 (17)
β (°)	106.848 (1)
V (Å³)	1816.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.43 × 0.28 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.710, 0.834
No. of measured, independent and observed [I > 2σ(I)] reflections	13254, 3296, 2627
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.231, 1.00
No. of reflections	3296
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.47, −0.33

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Mn1—O1	1.874 (3)	Mn1—N2	1.990 (5)
Mn1—O2	1.902 (3)	Mn1—N3	2.181 (5)
Mn1—N1	1.979 (4)	Mn1—O2ⁱ	2.557 (3)

O1—Mn1—O2	94.95 (14)	O2—Mn1—O2ⁱ	80.14 (14)
O1—Mn1—N1	92.1 (2)	N1—Mn1—N2	81.9 (2)
O1—Mn1—N2	170.90 (17)	N1—Mn1—N3	95.4 (2)
O1—Mn1—N3	93.94 (18)	N1—Mn1—O2ⁱ	87.29 (16)
O1—Mn1—O2ⁱ	88.62 (15)	N2—Mn1—N3	93.4 (2)
O2—Mn1—N1	165.40 (19)	N2—Mn1—O2ⁱ	84.35 (17)
O2—Mn1—N2	89.51 (17)	N3—Mn1—O2ⁱ	176.24 (17)
O2—Mn1—N3	96.85 (17)

Symmetry code: (i) −x+1, −y, −z.

Acknowledgements

The authors are grateful for financial support from Henan University (grant No. 05YBGG013).

References

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page m543

doi:10.1107/S1600536808003577

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

Bis{μ-2,2′-[ethane-1,2-diylbis(nitrilo­methyl­­idyne)]diphenolato}bis­­[(thio­cyanato)manganese(III)]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{μ-2,2′-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}bis[(thiocyanato)manganese(III)]