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Acta Cryst. (2009). E65, m306    [ doi:10.1107/S1600536809005352 ]

Chlorido{2,2'-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato-[kappa]4O,N,N',O'}manganese(III)

M.-J. Li, P.-F. Yan, G.-M. Li and H.-F. Li

Abstract top

In the title complex, [Mn(C17H16N2O2)Cl], the MnIII ion is coordinated by two O [Mn-O = 1.719 (2) and 1.813 (2) Å] and two N [Mn-N = 1.824 (2) and 1.931 (2) Å] atoms from the tetradentate Schiff base ligand and a chloride anion [Mn-Cl = 2.9634 (16) Å] in a square-pyramidal geometry. In the ligand, the two benzene rings form a dihedral angle of 68.06 (5)°.

Comment top

In the title compound (Fig. 1), the tetradentate Schiff base ligand links Mn atom into a mononuclear complex through two phenolate O atoms and two N atoms with the bond lengths similar to those reported for another manganese complex of the same ligand (Watkinson et al., 1999). The MnIII center is five-coordinate by two nitrogen atoms and two oxygen atoms from the ligand and one chlorine anion in a square-pyramidal geometry.

Related literature top

For a similar manganese complex of the same Schiff base, see: Watkinson et al. (1999).

Experimental top

The title complex was obtained by the treatment of manganese(III) chloride tetrahydrate with the Schiff base in methanol. The first two reactants were refluxed for 1 h. The reaction mixture was cooled and filtered; Diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Single crystals were obtained after several days. Analysis: calculated for C17H16MnN2O2Cl: C, 55.08; H, 4.35; Mn, 14.82; N, 7.56; found: C, 54.98; H, 4.39; N, 7.45; Mn, 14.28%.

Refinement top

H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic C), C—H = 0.97 Å (methylene C),and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids.
Chlorido{2,2'-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato- κ4O,N,N',O'}manganese(III) top
Crystal data top
[Mn(C17H16N2O2)Cl]F(000) = 760
Mr = 370.71Dx = 1.562 Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 12324 reflections
a = 10.428 (3) Åθ = 3.1–27.5°
b = 12.067 (4) ŵ = 1.02 mm−1
c = 12.530 (5) ÅT = 291 K
V = 1576.6 (10) Å3Block, black
Z = 40.19 × 0.17 × 0.12 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2689 independent reflections
Radiation source: fine-focus sealed tube2526 reflections with I > 2σ(I)
graphiteRint = 0.032
ω scansθmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −12→12
Tmin = 0.830, Tmax = 0.889k = −14→14
11321 measured reflectionsl = −13→13
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0666P)2 + 0.1785P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2689 reflectionsΔρmax = 0.44 e Å−3
208 parametersΔρmin = −0.30 e Å−3
1 restraintAbsolute structure: Flack (1983), 1227 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.01 (2)
Crystal data top
[Mn(C17H16N2O2)Cl]V = 1576.6 (10) Å3
Mr = 370.71Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 10.428 (3) ŵ = 1.02 mm−1
b = 12.067 (4) ÅT = 291 K
c = 12.530 (5) Å0.19 × 0.17 × 0.12 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer		2689 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		2526 reflections with I > 2σ(I)
Tmin = 0.830, Tmax = 0.889Rint = 0.032
11321 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.094Δρmax = 0.44 e Å−3
S = 1.05Δρmin = −0.30 e Å−3
2689 reflectionsAbsolute structure: Flack (1983), 1227 Friedel pairs
208 parametersFlack parameter: −0.01 (2)
1 restraint
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
C10.8363 (3)0.4885 (3)0.7136 (3)0.0330 (8)
C20.9063 (3)0.4297 (3)0.6323 (3)0.0383 (8)
H10.99180.45080.62570.046*
C30.8679 (3)0.3466 (3)0.5617 (3)0.0434 (9)
H20.92380.31670.51150.052*
C40.7560 (5)0.3148 (3)0.5694 (5)0.0550 (12)
H30.72040.26070.52560.066*
C50.6881 (3)0.3678 (3)0.6502 (4)0.0506 (11)
H40.60450.34260.65890.061*
C60.7247 (3)0.4555 (3)0.7232 (3)0.0365 (9)
C70.6476 (3)0.5107 (3)0.8041 (3)0.0365 (8)
H50.57380.47170.82240.044*
C80.5664 (3)0.6436 (3)0.9321 (3)0.0378 (8)
H70.60390.65381.00220.045*
H60.49340.59410.93760.045*
C90.5303 (3)0.7500 (3)0.8835 (3)0.0393 (8)
H80.53420.74250.80650.047*
H90.44210.76650.90240.047*
C100.6086 (3)0.8410 (3)0.9145 (3)0.0397 (9)
H100.56320.91060.90560.048*
H110.63520.83400.98840.048*
C110.7546 (3)0.9233 (3)0.8068 (3)0.0341 (8)
H120.70550.98530.82310.041*
C120.8596 (3)0.9429 (3)0.7439 (3)0.0342 (8)
C130.8794 (3)1.0423 (3)0.6866 (4)0.0468 (10)
H130.81801.09760.69470.056*
C140.9749 (4)1.0638 (3)0.6237 (4)0.0499 (10)
H140.98151.12860.58390.060*
C151.0592 (3)0.9870 (3)0.6221 (3)0.0455 (10)
H151.13230.99600.58050.055*
C161.0440 (3)0.8901 (3)0.6812 (3)0.0422 (9)
H161.11070.83900.67870.051*
C170.9428 (3)0.8637 (3)0.7408 (3)0.0320 (8)
Cl10.82072 (8)0.70229 (8)1.06882 (7)0.0435 (2)
Mn10.79832 (4)0.69247 (3)0.83324 (5)0.03055 (16)
N10.6603 (2)0.6027 (2)0.8558 (2)0.0319 (7)
N20.7160 (2)0.8353 (2)0.8449 (3)0.0303 (6)
O10.87583 (19)0.56992 (19)0.7799 (2)0.0435 (6)
O20.92804 (19)0.76783 (19)0.7896 (2)0.0457 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0170 (15)0.0230 (17)0.059 (2)0.0016 (12)−0.0073 (14)0.0037 (14)
C20.0165 (15)0.0260 (17)0.072 (3)0.0026 (13)−0.0026 (16)0.0053 (15)
C30.0275 (17)0.0269 (17)0.076 (3)0.0054 (14)−0.0028 (18)−0.0031 (17)
C40.0323 (18)0.0296 (17)0.103 (4)−0.0024 (16)−0.012 (2)−0.015 (2)
C50.0223 (17)0.0280 (18)0.101 (3)−0.0069 (14)−0.0072 (19)0.004 (2)
C60.0206 (17)0.0237 (16)0.065 (3)−0.0017 (13)−0.0096 (15)0.0087 (15)
C70.0142 (13)0.0296 (17)0.066 (2)−0.0035 (12)−0.0056 (14)0.0123 (16)
C80.0157 (14)0.044 (2)0.053 (2)−0.0016 (13)0.0046 (14)0.0005 (16)
C90.0135 (14)0.044 (2)0.060 (2)0.0056 (13)0.0084 (15)−0.0050 (16)
C100.0215 (15)0.0381 (19)0.060 (2)0.0082 (14)0.0048 (15)−0.0085 (16)
C110.0183 (13)0.0324 (17)0.052 (2)0.0076 (13)−0.0021 (14)−0.0019 (14)
C120.0198 (15)0.0224 (15)0.060 (2)−0.0009 (12)−0.0024 (15)−0.0026 (15)
C130.0268 (18)0.0245 (18)0.089 (3)−0.0020 (13)−0.005 (2)0.0033 (18)
C140.035 (2)0.0296 (18)0.085 (3)−0.0068 (16)−0.013 (2)0.0107 (18)
C150.0271 (17)0.040 (2)0.069 (3)−0.0159 (16)−0.0009 (17)0.0012 (18)
C160.0193 (16)0.0310 (18)0.076 (3)−0.0047 (13)−0.0011 (17)−0.0065 (18)
C170.0171 (15)0.0253 (17)0.054 (2)−0.0036 (12)−0.0080 (14)−0.0018 (15)
Cl10.0340 (4)0.0450 (5)0.0516 (6)−0.0052 (4)−0.0144 (4)0.0071 (4)
Mn10.0114 (2)0.0231 (2)0.0571 (3)0.00044 (15)−0.0008 (2)0.0015 (3)
N10.0106 (10)0.0306 (14)0.0544 (19)0.0022 (9)−0.0040 (11)0.0068 (13)
N20.0120 (10)0.0291 (13)0.0499 (17)0.0028 (9)−0.0012 (12)−0.0002 (15)
O10.0079 (9)0.0278 (12)0.0949 (18)0.0026 (8)−0.0058 (11)−0.0085 (12)
O20.0087 (9)0.0268 (12)0.101 (2)0.0014 (8)−0.0015 (11)0.0066 (13)
Geometric parameters (Å, °) top
C1—C61.236 (5)C10—H100.9700
C1—O11.351 (4)C10—H110.9700
C1—C21.439 (5)C11—N21.232 (4)
C2—C31.397 (5)C11—C121.370 (5)
C2—H10.9300C11—H120.9300
C3—C41.232 (6)C12—C171.292 (5)
C3—H20.9300C12—C131.413 (5)
C4—C51.391 (7)C13—C141.296 (6)
C4—H30.9300C13—H130.9300
C5—C61.449 (6)C14—C151.277 (5)
C5—H40.9300C14—H140.9300
C6—C71.456 (5)C15—C161.394 (5)
C7—N11.291 (4)C15—H150.9300
C7—H50.9300C16—C171.331 (5)
C8—N11.455 (4)C16—H160.9300
C8—C91.470 (5)C17—O21.317 (4)
C8—H70.9700Cl1—Mn12.9634 (16)
C8—H60.9700Mn1—O21.719 (2)
C9—C101.423 (5)Mn1—O11.813 (2)
C9—H80.9700Mn1—N11.824 (2)
C9—H90.9700Mn1—N21.931 (2)
C10—N21.421 (4)
C6—C1—O1117.5 (3)N2—C11—C12129.3 (3)
C6—C1—C2112.9 (3)N2—C11—H12115.4
O1—C1—C2129.6 (3)C12—C11—H12115.4
C3—C2—C1131.0 (3)C17—C12—C11115.2 (3)
C3—C2—H1114.5C17—C12—C13121.0 (3)
C1—C2—H1114.5C11—C12—C13123.8 (3)
C4—C3—C2116.5 (4)C14—C13—C12126.3 (4)
C4—C3—H2121.8C14—C13—H13116.9
C2—C3—H2121.8C12—C13—H13116.9
C3—C4—C5113.3 (4)C15—C14—C13113.1 (4)
C3—C4—H3123.3C15—C14—H14123.4
C5—C4—H3123.3C13—C14—H14123.4
C4—C5—C6131.4 (3)C14—C15—C16121.5 (4)
C4—C5—H4114.3C14—C15—H15119.3
C6—C5—H4114.3C16—C15—H15119.3
C1—C6—C5114.9 (4)C17—C16—C15126.1 (3)
C1—C6—C7116.1 (3)C17—C16—H16116.9
C5—C6—C7128.9 (3)C15—C16—H16116.9
N1—C7—C6133.3 (3)C12—C17—O2123.9 (3)
N1—C7—H5113.4C12—C17—C16111.8 (3)
C6—C7—H5113.4O2—C17—C16124.3 (3)
N1—C8—C9101.3 (3)O2—Mn1—O187.90 (11)
N1—C8—H7111.5O2—Mn1—N1169.92 (14)
C9—C8—H7111.5O1—Mn1—N185.65 (11)
N1—C8—H6111.5O2—Mn1—N284.35 (11)
C9—C8—H6111.5O1—Mn1—N2162.58 (14)
H7—C8—H6109.3N1—Mn1—N299.68 (11)
C10—C9—C8114.5 (3)O2—Mn1—Cl1103.51 (11)
C10—C9—H8108.6O1—Mn1—Cl1111.39 (10)
C8—C9—H8108.6N1—Mn1—Cl186.08 (9)
C10—C9—H9108.6N2—Mn1—Cl185.64 (10)
C8—C9—H9108.6C7—N1—C8123.5 (3)
H8—C9—H9107.6C7—N1—Mn1120.9 (2)
N2—C10—C9104.3 (3)C8—N1—Mn1115.6 (2)
N2—C10—H10110.9C11—N2—C10117.0 (3)
C9—C10—H10110.9C11—N2—Mn1126.5 (2)
N2—C10—H11110.9C10—N2—Mn1116.1 (2)
C9—C10—H11110.9C1—O1—Mn1133.14 (19)
H10—C10—H11108.9C17—O2—Mn1134.8 (2)
Acknowledgements top

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (grant Nos. 20572018 and 20672032), Heilongjiang Province (grant Nos. 1055HZ001, ZJG0504 and JC200605) and Heilongjiang University.

references
References top

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

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

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

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

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

Watkinson, M., Fondo, M., Bermejo, M. R., Sousa, A., McAuliffe, C. A., Pritchard, R. G., Jaiboon, N., Aurangzeb, N. & Naeem, M. (1999). J. Chem. Soc. Dalton Trans. pp. 31–41. Please check date – was 1999 in Comment