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Acta Cryst. (2009). E65, m634    [ doi:10.1107/S160053680901681X ]

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

M. Zhong, J.-H. Lin, J. Shang, T.-H. Huang and X.-J. Wang

Abstract top

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.

Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] 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.]
[Figure 2] Fig. 2. Crystal packing of the title compound, showing hydrogen bonds (dashed lines).
Bis[4-(2-hydroxybenzylideneamino)benzoato-κO]tetrakis(methanol- κO)manganese(II) top
Crystal data top
[Mn(C14H10NO3)2(CH4O)4]F000 = 694
Mr = 663.57Dx = 1.416 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3622 reflections
a = 15.0341 (6) Åθ = 2.7–29.8º
b = 11.8819 (4) ŵ = 0.49 mm−1
c = 8.8178 (3) ÅT = 293 K
β = 98.912 (4)ºBlock, colorless
V = 1556.14 (10) Å30.6 × 0.6 × 0.3 mm
Z = 2
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer		3374 independent reflections
Radiation source: Enhance (Mo) X-ray Source2008 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.032
Detector resolution: 16.0855 pixels mm-1θmax = 27.0º
T = 293 Kθmin = 2.7º
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 top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.102  w = 1/[σ2(Fo2) + (0.058P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
3374 reflectionsΔρmax = 0.55 e Å−3
205 parametersΔρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Mn(C14H10NO3)2(CH4O)4]V = 1556.14 (10) Å3
Mr = 663.57Z = 2
Monoclinic, P21/cMo Kα
a = 15.0341 (6) ŵ = 0.49 mm−1
b = 11.8819 (4) ÅT = 293 K
c = 8.8178 (3) Å0.6 × 0.6 × 0.3 mm
β = 98.912 (4)º
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer		3374 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)		2008 reflections with I > 2σ(I)
Tmin = 0.823, Tmax = 1.000Rint = 0.032
10167 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039205 parameters
wR(F2) = 0.102H-atom parameters constrained
S = 0.92Δρmax = 0.55 e Å−3
3374 reflectionsΔρmin = −0.31 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Selected geometric parameters (Å) top
Mn1—O32.1275 (15)Mn1—O42.2023 (14)
Mn1—O52.1803 (13)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N10.851.832.619 (2)153
O4—H4B···O2i0.851.842.621 (2)151
O5—H5B···O20.851.832.618 (2)153
Symmetry codes: (i) −x+1, y+1/2, −z+1/2.
Acknowledgements top

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

references
References top

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