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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): m306.
Published online 2009 February 21. doi:  10.1107/S1600536809005352
PMCID: PMC2968646

Chlorido{2,2′-[propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato-κ4 O,N,N′,O′}manganese(III)

Abstract

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)°.

Related literature

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

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Object name is e-65-0m306-scheme1.jpg

Experimental

Crystal data

  • [Mn(C17H16N2O2)Cl]
  • M r = 370.71
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m306-efi1.jpg
  • a = 10.428 (3) Å
  • b = 12.067 (4) Å
  • c = 12.530 (5) Å
  • V = 1576.6 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.02 mm−1
  • T = 291 K
  • 0.19 × 0.17 × 0.12 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.830, T max = 0.889
  • 11321 measured reflections
  • 2689 independent reflections
  • 2526 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.094
  • S = 1.05
  • 2689 reflections
  • 208 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.44 e Å−3
  • Δρmin = −0.31 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1227 Friedel pairs
  • Flack parameter: −0.01 (2)

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005352/cv2500sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005352/cv2500Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of (I), showing 30% probability displacement ellipsoids.

Crystal data

[Mn(C17H16N2O2)Cl]F(000) = 760
Mr = 370.71Dx = 1.562 Mg m3
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 mm1
c = 12.530 (5) ÅT = 291 K
V = 1576.6 (10) Å3Block, black
Z = 40.19 × 0.17 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer2689 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

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) = 0.094w = 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 Å3
208 parametersΔρmin = −0.30 e Å3
1 restraintAbsolute structure: Flack (1983), 1227 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.01 (2)

Special details

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)

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2500).

References

  • 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. [PubMed]
  • 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.

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