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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): m634.
Published online 2009 May 14. doi:  10.1107/S160053680901681X
PMCID: PMC2969834

Bis[4-(2-hydroxy­benzyl­ideneamino)benzoato-κO]tetrakis­(methanol-κO)manganese(II)

Abstract

In the title mononuclear complex, [Mn(C14H10NO3)2(CH3OH)4], the MnII atom, lying on an inversion centre, exhibits a distorted octa­hedral geometry, defined by two O atoms from two monodentate ligands and four O atoms from four methanol mol­ecules. The crystal structure involves intra­molecular O—H(...)N and O—H(...)O and inter­molecular O—H(...)O hydrogen bonds.

Related literature

For general background, see: Deeth (2008 [triangle]); Dubois et al. (2008 [triangle]); Huang et al. (2004 [triangle]).

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Object name is e-65-0m634-scheme1.jpg

Experimental

Crystal data

  • [Mn(C14H10NO3)2(CH4O)4]
  • M r = 663.57
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m634-efi1.jpg
  • a = 15.0341 (6) Å
  • b = 11.8819 (4) Å
  • c = 8.8178 (3) Å
  • β = 98.912 (4)°
  • V = 1556.14 (10) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.49 mm−1
  • T = 293 K
  • 0.6 × 0.6 × 0.3 mm

Data collection

  • Oxford Diffraction Gemini S Ultra diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 [triangle]) T min = 0.823, T max = 1.000 (expected range = 0.711–0.865)
  • 10167 measured reflections
  • 3374 independent reflections
  • 2008 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.102
  • S = 0.92
  • 3374 reflections
  • 205 parameters
  • H-atom parameters constrained
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 [triangle]); data reduction: CrysAlis RED; 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]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053680901681X/hy2192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901681X/hy2192Isup2.hkl

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

Acknowledgments

This work was supported by the Natural Science Foundation of Guangxi Province of China (grant No. 0832100).

supplementary crystallographic information

Comment

General molecular mechanics method for transition metal carboxylates and the multiple coordination modes in manganese(II) complexes have been reported recently (Deeth, 2008). Information on the structures of manganese(II) carboxylates continues to be collected, and at the same time new applications of such complexes are being discovered in magnetic properties, potential biological significance and ferrimagnet (Huang et al., 2004). The chemistry of organo-manganese(II) complexes of Schiff base has stemmed from the reported biocidal and catalytic activities of organo-manganese(II) compounds (Dubois et al., 2008). We report here a new monomeric manganese(II) compound, which contains the Schiff base ligand, N-(4-carboxyphenyl)salicylideneimine (Fig.1). The MnII atom has a distorted octahedral geometry (Table 1). There exist intra- and intermolecular hydrogen bonds in the crystal structure (Table 2). The intermolecular hydrogen bonds is used to form a two-dimensional supramolecular network (Fig. 2).

Experimental

Manganese(II) acetate tetrahydrate (0.049 g, 0.2 mmol) was dissolved in 8 ml deionized water, giving a transparent solution (A), and N-(4-carboxyphenyl)salicylideneimine (0.097 g, 0.4 mmol) was dissolved in 10 ml me thanol (B). Then solution B was mixed with A and a suspension was obtained. Ammonia was added to the above mixture dropwise under magnetic stirring until pH value is neutral. The resulting suspension was transferred into a 25 ml Teflon-lined stainless-steel autoclave. The autoclave was sealed and maintained at 363 K for 12 h under autogenous pressure. After the reaction was completed, the resulting colourless block crystals were collected by filtration.

Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic) and 0.96 (CH3) Å and O—H = 0.85 Å, and with Uiso(H) = 1.2Ueq(C,O).

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (i) -x + 1, -y, -z.]
Fig. 2.
Crystal packing of the title compound, showing hydrogen bonds (dashed lines).

Crystal data

[Mn(C14H10NO3)2(CH4O)4]F(000) = 694
Mr = 663.57Dx = 1.416 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3622 reflections
a = 15.0341 (6) Åθ = 2.7–29.8°
b = 11.8819 (4) ŵ = 0.49 mm1
c = 8.8178 (3) ÅT = 293 K
β = 98.912 (4)°Block, colorless
V = 1556.14 (10) Å30.6 × 0.6 × 0.3 mm
Z = 2

Data collection

Oxford Diffraction Gemini S Ultra diffractometer3374 independent reflections
Radiation source: Enhance (Mo) X-ray Source2008 reflections with I > 2σ(I)
graphiteRint = 0.032
Detector resolution: 16.0855 pixels mm-1θmax = 27.0°, θmin = 2.7°
ω scansh = −19→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)k = −15→14
Tmin = 0.823, Tmax = 1.000l = −11→11
10167 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 0.92w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3
3374 reflections(Δ/σ)max < 0.001
205 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = −0.31 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Mn10.50000.00000.00000.02171 (15)
O11.09324 (11)0.03911 (14)0.80222 (19)0.0404 (4)
H1A1.04200.02100.75330.048*
O20.57922 (10)−0.20216 (13)0.26345 (18)0.0350 (4)
O30.60735 (10)−0.03061 (12)0.18268 (17)0.0291 (4)
N10.94227 (12)−0.06941 (15)0.7155 (2)0.0295 (5)
C11.11213 (15)−0.0410 (2)0.9117 (3)0.0303 (6)
C21.19528 (16)−0.0391 (2)1.0049 (3)0.0360 (6)
H2A1.23780.01510.99040.043*
C31.21437 (16)−0.1187 (2)1.1196 (3)0.0397 (6)
H3A1.2704−0.11771.18150.048*
C41.15283 (15)−0.1989 (2)1.1442 (3)0.0377 (6)
H4A1.1665−0.25111.22290.045*
C51.07051 (15)−0.2014 (2)1.0510 (3)0.0332 (6)
H5A1.0288−0.25611.06750.040*
C61.04831 (14)−0.12450 (18)0.9335 (2)0.0276 (5)
C70.96278 (15)−0.13309 (19)0.8321 (3)0.0306 (5)
H7A0.9215−0.18700.85290.037*
C80.86185 (14)−0.08573 (19)0.6112 (2)0.0269 (5)
C90.81878 (14)−0.18938 (19)0.5844 (3)0.0312 (6)
H9A0.8412−0.25240.64020.037*
C100.74265 (14)−0.19842 (19)0.4748 (3)0.0299 (5)
H10A0.7137−0.26750.45870.036*
C110.70884 (14)−0.10594 (17)0.3887 (2)0.0225 (5)
C120.75350 (15)−0.00380 (18)0.4146 (2)0.0259 (5)
H12A0.73220.05870.35670.031*
C130.82848 (15)0.00641 (19)0.5241 (2)0.0279 (5)
H13A0.85720.07570.54010.033*
C140.62646 (14)−0.11436 (18)0.2699 (2)0.0234 (5)
O40.42496 (10)0.08439 (12)0.16313 (16)0.0306 (4)
H4B0.43710.15430.16660.037*
O50.43893 (10)−0.15779 (11)0.05698 (16)0.0271 (4)
H5B0.4791−0.19380.11630.033*
C150.42208 (19)0.0436 (2)0.3134 (3)0.0436 (7)
H15A0.38620.09320.36500.065*
H15B0.48210.04030.36950.065*
H15C0.3960−0.03030.30750.065*
C160.39223 (16)−0.23800 (19)−0.0468 (3)0.0368 (6)
H16A0.3730−0.29990.01030.055*
H16B0.4316−0.2651−0.11450.055*
H16C0.3406−0.2029−0.10580.055*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.0265 (3)0.0162 (2)0.0218 (3)−0.0006 (2)0.00172 (19)0.0002 (2)
O10.0353 (10)0.0405 (10)0.0447 (11)−0.0090 (8)0.0041 (8)0.0001 (9)
O20.0365 (9)0.0240 (9)0.0407 (10)−0.0064 (7)−0.0061 (8)0.0091 (8)
O30.0313 (9)0.0259 (9)0.0282 (9)−0.0022 (7)−0.0011 (7)0.0067 (7)
N10.0296 (11)0.0303 (11)0.0282 (10)−0.0001 (9)0.0029 (9)−0.0037 (9)
C10.0333 (14)0.0307 (13)0.0272 (12)0.0057 (10)0.0061 (11)−0.0047 (11)
C20.0260 (13)0.0373 (14)0.0454 (15)−0.0033 (11)0.0077 (12)−0.0122 (12)
C30.0247 (14)0.0523 (17)0.0392 (15)0.0064 (12)−0.0040 (11)−0.0083 (13)
C40.0366 (14)0.0417 (15)0.0331 (14)0.0070 (12)0.0002 (12)0.0001 (12)
C50.0286 (13)0.0352 (14)0.0354 (14)−0.0022 (11)0.0035 (11)−0.0022 (12)
C60.0223 (12)0.0336 (13)0.0271 (12)0.0010 (10)0.0044 (10)−0.0069 (11)
C70.0304 (13)0.0313 (13)0.0302 (13)−0.0033 (10)0.0053 (11)−0.0027 (11)
C80.0245 (12)0.0312 (13)0.0249 (12)−0.0004 (10)0.0036 (10)−0.0059 (10)
C90.0293 (13)0.0247 (13)0.0373 (14)0.0055 (10)−0.0015 (11)0.0034 (11)
C100.0293 (13)0.0226 (12)0.0355 (14)−0.0011 (10)−0.0022 (11)−0.0010 (11)
C110.0252 (12)0.0214 (11)0.0225 (11)0.0003 (9)0.0086 (10)−0.0014 (9)
C120.0330 (12)0.0224 (11)0.0223 (11)0.0000 (11)0.0043 (9)0.0032 (10)
C130.0336 (13)0.0244 (12)0.0251 (11)−0.0048 (11)0.0025 (10)−0.0020 (11)
C140.0276 (12)0.0201 (12)0.0237 (11)0.0025 (10)0.0075 (10)−0.0001 (10)
O40.0433 (10)0.0183 (8)0.0317 (9)0.0003 (7)0.0105 (7)−0.0017 (7)
O50.0306 (8)0.0180 (8)0.0309 (9)−0.0023 (7)−0.0010 (7)0.0019 (7)
C150.070 (2)0.0313 (13)0.0339 (14)−0.0014 (13)0.0207 (14)0.0006 (12)
C160.0417 (15)0.0264 (13)0.0415 (15)−0.0077 (11)0.0041 (12)−0.0096 (11)

Geometric parameters (Å, °)

Mn1—O32.1275 (15)C7—H7A0.9300
Mn1—O3i2.1275 (15)C8—C131.386 (3)
Mn1—O5i2.1802 (13)C8—C91.394 (3)
Mn1—O52.1803 (13)C9—C101.383 (3)
Mn1—O42.2023 (14)C9—H9A0.9300
Mn1—O4i2.2023 (14)C10—C111.387 (3)
O1—C11.354 (3)C10—H10A0.9300
O1—H1A0.8500C11—C121.389 (3)
O2—C141.258 (2)C11—C141.496 (3)
O3—C141.263 (2)C12—C131.372 (3)
N1—C71.275 (3)C12—H12A0.9300
N1—C81.415 (3)C13—H13A0.9300
C1—C21.386 (3)O4—C151.418 (3)
C1—C61.414 (3)O4—H4B0.8500
C2—C31.382 (3)O5—C161.428 (2)
C2—H2A0.9300O5—H5B0.8500
C3—C41.369 (3)C15—H15A0.9600
C3—H3A0.9300C15—H15B0.9600
C4—C51.376 (3)C15—H15C0.9600
C4—H4A0.9300C16—H16A0.9600
C5—C61.383 (3)C16—H16B0.9600
C5—H5A0.9300C16—H16C0.9600
C6—C71.452 (3)
O3—Mn1—O3i180.00 (10)C13—C8—C9119.0 (2)
O3—Mn1—O5i91.39 (5)C13—C8—N1116.85 (19)
O3i—Mn1—O5i88.61 (5)C9—C8—N1124.0 (2)
O3—Mn1—O588.61 (5)C10—C9—C8120.0 (2)
O3i—Mn1—O591.39 (5)C10—C9—H9A120.0
O5i—Mn1—O5180.00 (7)C8—C9—H9A120.0
O3—Mn1—O489.34 (6)C9—C10—C11121.0 (2)
O3i—Mn1—O490.66 (6)C9—C10—H10A119.5
O5i—Mn1—O492.04 (5)C11—C10—H10A119.5
O5—Mn1—O487.96 (5)C10—C11—C12118.4 (2)
O3—Mn1—O4i90.66 (6)C10—C11—C14121.60 (19)
O3i—Mn1—O4i89.34 (6)C12—C11—C14120.02 (19)
O5i—Mn1—O4i87.96 (5)C13—C12—C11121.1 (2)
O5—Mn1—O4i92.04 (5)C13—C12—H12A119.4
O4—Mn1—O4i180.00 (7)C11—C12—H12A119.4
C1—O1—H1A104.9C12—C13—C8120.5 (2)
C14—O3—Mn1132.05 (14)C12—C13—H13A119.7
C7—N1—C8121.23 (19)C8—C13—H13A119.7
O1—C1—C2118.8 (2)O2—C14—O3123.5 (2)
O1—C1—C6121.2 (2)O2—C14—C11119.14 (19)
C2—C1—C6120.0 (2)O3—C14—C11117.32 (18)
C3—C2—C1119.3 (2)C15—O4—Mn1123.20 (14)
C3—C2—H2A120.4C15—O4—H4B109.7
C1—C2—H2A120.4Mn1—O4—H4B109.9
C4—C3—C2121.6 (2)C16—O5—Mn1127.52 (13)
C4—C3—H3A119.2C16—O5—H5B106.9
C2—C3—H3A119.2Mn1—O5—H5B106.9
C3—C4—C5119.2 (2)O4—C15—H15A109.5
C3—C4—H4A120.4O4—C15—H15B109.5
C5—C4—H4A120.4H15A—C15—H15B109.5
C4—C5—C6121.6 (2)O4—C15—H15C109.5
C4—C5—H5A119.2H15A—C15—H15C109.5
C6—C5—H5A119.2H15B—C15—H15C109.5
C5—C6—C1118.4 (2)O5—C16—H16A109.5
C5—C6—C7120.2 (2)O5—C16—H16B109.5
C1—C6—C7121.4 (2)H16A—C16—H16B109.5
N1—C7—C6122.4 (2)O5—C16—H16C109.5
N1—C7—H7A118.8H16A—C16—H16C109.5
C6—C7—H7A118.8H16B—C16—H16C109.5
O5i—Mn1—O3—C14−173.33 (18)C8—C9—C10—C111.0 (3)
O5—Mn1—O3—C146.67 (18)C9—C10—C11—C120.3 (3)
O4—Mn1—O3—C1494.64 (19)C9—C10—C11—C14−179.90 (18)
O4i—Mn1—O3—C14−85.36 (19)C10—C11—C12—C13−1.0 (3)
O1—C1—C2—C3178.3 (2)C14—C11—C12—C13179.17 (18)
C6—C1—C2—C3−0.6 (3)C11—C12—C13—C80.4 (3)
C1—C2—C3—C4−0.5 (4)C9—C8—C13—C120.8 (3)
C2—C3—C4—C51.0 (4)N1—C8—C13—C12176.55 (18)
C3—C4—C5—C6−0.2 (3)Mn1—O3—C14—O2−1.2 (3)
C4—C5—C6—C1−0.9 (3)Mn1—O3—C14—C11−179.75 (12)
C4—C5—C6—C7176.7 (2)C10—C11—C14—O210.7 (3)
O1—C1—C6—C5−177.6 (2)C12—C11—C14—O2−169.4 (2)
C2—C1—C6—C51.3 (3)C10—C11—C14—O3−170.6 (2)
O1—C1—C6—C74.8 (3)C12—C11—C14—O39.2 (3)
C2—C1—C6—C7−176.2 (2)O3—Mn1—O4—C15−41.12 (17)
C8—N1—C7—C6174.53 (19)O3i—Mn1—O4—C15138.88 (17)
C5—C6—C7—N1−174.7 (2)O5i—Mn1—O4—C15−132.49 (17)
C1—C6—C7—N12.8 (3)O5—Mn1—O4—C1547.51 (17)
C7—N1—C8—C13157.1 (2)O3—Mn1—O5—C16−142.12 (16)
C7—N1—C8—C9−27.4 (3)O3i—Mn1—O5—C1637.88 (16)
C13—C8—C9—C10−1.5 (3)O4—Mn1—O5—C16128.49 (16)
N1—C8—C9—C10−176.92 (19)O4i—Mn1—O5—C16−51.51 (16)

Symmetry codes: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.851.832.619 (2)153
O4—H4B···O2ii0.851.842.621 (2)151
O5—H5B···O20.851.832.618 (2)153

Symmetry codes: (ii) −x+1, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2192).

References

  • Deeth, R. J. (2008). Inorg. Chem.47, 6711–6725. [PubMed]
  • Dubois, L., Pécaut, J., Charlot, M.-F., Baffert, C., Collomb, M.-N., Deronzier, A. & Latour, J.-M. (2008). Chem. Eur. J.14, 3013–3025. [PubMed]
  • Huang, D., Wang, W., Zhang, X., Chen, C., Chen, F., Liu, Q., Liao, D., Li, L. & Sun, L. (2004). Eur. J. Inorg. Chem. pp. 1454–1464.
  • Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst.39, 453–457.
  • Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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