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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 May 14;65(Pt 6):m634. doi: 10.1107/S160053680901681X

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

Min Zhong a,*, Jia-Huang Lin a, Jing Shang a, Ting-Hong Huang a, Xiu-Jian Wang a
PMCID: PMC2969834  PMID: 21583002

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); Dubois et al. (2008); Huang et al. (2004).graphic file with name e-65-0m634-scheme1.jpg

Experimental

Crystal data

  • [Mn(C14H10NO3)2(CH4O)4]

  • M r = 663.57

  • Monoclinic, Inline graphic

  • 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) 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); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; 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.

Supplementary Material

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

e-65-0m634-sup1.cif (19.1KB, cif)

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

e-65-0m634-Isup2.hkl (165.5KB, hkl)

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

Table 1. Selected bond lengths (Å).

Mn1—O3 2.1275 (15)
Mn1—O5 2.1803 (13)
Mn1—O4 2.2023 (14)

Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯N1 0.85 1.83 2.619 (2) 153
O4—H4B⋯O2i 0.85 1.84 2.621 (2) 151
O5—H5B⋯O2 0.85 1.83 2.618 (2) 153

Symmetry code: (i) Inline graphic.

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.

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.

Fig. 2.

Crystal packing of the title compound, showing hydrogen bonds (dashed lines).

Crystal data

[Mn(C14H10NO3)2(CH4O)4] F(000) = 694
Mr = 663.57 Dx = 1.416 Mg m3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 3622 reflections
a = 15.0341 (6) Å θ = 2.7–29.8°
b = 11.8819 (4) Å µ = 0.49 mm1
c = 8.8178 (3) Å T = 293 K
β = 98.912 (4)° Block, colorless
V = 1556.14 (10) Å3 0.6 × 0.6 × 0.3 mm
Z = 2

Data collection

Oxford Diffraction Gemini S Ultra diffractometer 3374 independent reflections
Radiation source: Enhance (Mo) X-ray Source 2008 reflections with I > 2σ(I)
graphite Rint = 0.032
Detector resolution: 16.0855 pixels mm-1 θmax = 27.0°, θmin = 2.7°
ω scans h = −19→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) k = −15→14
Tmin = 0.823, Tmax = 1.000 l = −11→11
10167 measured reflections

Refinement

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)] = 0.039 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102 H-atom parameters constrained
S = 0.92 w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3
3374 reflections (Δ/σ)max < 0.001
205 parameters Δρmax = 0.55 e Å3
0 restraints Δρmin = −0.31 e Å3

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

x y z Uiso*/Ueq
Mn1 0.5000 0.0000 0.0000 0.02171 (15)
O1 1.09324 (11) 0.03911 (14) 0.80222 (19) 0.0404 (4)
H1A 1.0420 0.0210 0.7533 0.048*
O2 0.57922 (10) −0.20216 (13) 0.26345 (18) 0.0350 (4)
O3 0.60735 (10) −0.03061 (12) 0.18268 (17) 0.0291 (4)
N1 0.94227 (12) −0.06941 (15) 0.7155 (2) 0.0295 (5)
C1 1.11213 (15) −0.0410 (2) 0.9117 (3) 0.0303 (6)
C2 1.19528 (16) −0.0391 (2) 1.0049 (3) 0.0360 (6)
H2A 1.2378 0.0151 0.9904 0.043*
C3 1.21437 (16) −0.1187 (2) 1.1196 (3) 0.0397 (6)
H3A 1.2704 −0.1177 1.1815 0.048*
C4 1.15283 (15) −0.1989 (2) 1.1442 (3) 0.0377 (6)
H4A 1.1665 −0.2511 1.2229 0.045*
C5 1.07051 (15) −0.2014 (2) 1.0510 (3) 0.0332 (6)
H5A 1.0288 −0.2561 1.0675 0.040*
C6 1.04831 (14) −0.12450 (18) 0.9335 (2) 0.0276 (5)
C7 0.96278 (15) −0.13309 (19) 0.8321 (3) 0.0306 (5)
H7A 0.9215 −0.1870 0.8529 0.037*
C8 0.86185 (14) −0.08573 (19) 0.6112 (2) 0.0269 (5)
C9 0.81878 (14) −0.18938 (19) 0.5844 (3) 0.0312 (6)
H9A 0.8412 −0.2524 0.6402 0.037*
C10 0.74265 (14) −0.19842 (19) 0.4748 (3) 0.0299 (5)
H10A 0.7137 −0.2675 0.4587 0.036*
C11 0.70884 (14) −0.10594 (17) 0.3887 (2) 0.0225 (5)
C12 0.75350 (15) −0.00380 (18) 0.4146 (2) 0.0259 (5)
H12A 0.7322 0.0587 0.3567 0.031*
C13 0.82848 (15) 0.00641 (19) 0.5241 (2) 0.0279 (5)
H13A 0.8572 0.0757 0.5401 0.033*
C14 0.62646 (14) −0.11436 (18) 0.2699 (2) 0.0234 (5)
O4 0.42496 (10) 0.08439 (12) 0.16313 (16) 0.0306 (4)
H4B 0.4371 0.1543 0.1666 0.037*
O5 0.43893 (10) −0.15779 (11) 0.05698 (16) 0.0271 (4)
H5B 0.4791 −0.1938 0.1163 0.033*
C15 0.42208 (19) 0.0436 (2) 0.3134 (3) 0.0436 (7)
H15A 0.3862 0.0932 0.3650 0.065*
H15B 0.4821 0.0403 0.3695 0.065*
H15C 0.3960 −0.0303 0.3075 0.065*
C16 0.39223 (16) −0.23800 (19) −0.0468 (3) 0.0368 (6)
H16A 0.3730 −0.2999 0.0103 0.055*
H16B 0.4316 −0.2651 −0.1145 0.055*
H16C 0.3406 −0.2029 −0.1058 0.055*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Mn1 0.0265 (3) 0.0162 (2) 0.0218 (3) −0.0006 (2) 0.00172 (19) 0.0002 (2)
O1 0.0353 (10) 0.0405 (10) 0.0447 (11) −0.0090 (8) 0.0041 (8) 0.0001 (9)
O2 0.0365 (9) 0.0240 (9) 0.0407 (10) −0.0064 (7) −0.0061 (8) 0.0091 (8)
O3 0.0313 (9) 0.0259 (9) 0.0282 (9) −0.0022 (7) −0.0011 (7) 0.0067 (7)
N1 0.0296 (11) 0.0303 (11) 0.0282 (10) −0.0001 (9) 0.0029 (9) −0.0037 (9)
C1 0.0333 (14) 0.0307 (13) 0.0272 (12) 0.0057 (10) 0.0061 (11) −0.0047 (11)
C2 0.0260 (13) 0.0373 (14) 0.0454 (15) −0.0033 (11) 0.0077 (12) −0.0122 (12)
C3 0.0247 (14) 0.0523 (17) 0.0392 (15) 0.0064 (12) −0.0040 (11) −0.0083 (13)
C4 0.0366 (14) 0.0417 (15) 0.0331 (14) 0.0070 (12) 0.0002 (12) 0.0001 (12)
C5 0.0286 (13) 0.0352 (14) 0.0354 (14) −0.0022 (11) 0.0035 (11) −0.0022 (12)
C6 0.0223 (12) 0.0336 (13) 0.0271 (12) 0.0010 (10) 0.0044 (10) −0.0069 (11)
C7 0.0304 (13) 0.0313 (13) 0.0302 (13) −0.0033 (10) 0.0053 (11) −0.0027 (11)
C8 0.0245 (12) 0.0312 (13) 0.0249 (12) −0.0004 (10) 0.0036 (10) −0.0059 (10)
C9 0.0293 (13) 0.0247 (13) 0.0373 (14) 0.0055 (10) −0.0015 (11) 0.0034 (11)
C10 0.0293 (13) 0.0226 (12) 0.0355 (14) −0.0011 (10) −0.0022 (11) −0.0010 (11)
C11 0.0252 (12) 0.0214 (11) 0.0225 (11) 0.0003 (9) 0.0086 (10) −0.0014 (9)
C12 0.0330 (12) 0.0224 (11) 0.0223 (11) 0.0000 (11) 0.0043 (9) 0.0032 (10)
C13 0.0336 (13) 0.0244 (12) 0.0251 (11) −0.0048 (11) 0.0025 (10) −0.0020 (11)
C14 0.0276 (12) 0.0201 (12) 0.0237 (11) 0.0025 (10) 0.0075 (10) −0.0001 (10)
O4 0.0433 (10) 0.0183 (8) 0.0317 (9) 0.0003 (7) 0.0105 (7) −0.0017 (7)
O5 0.0306 (8) 0.0180 (8) 0.0309 (9) −0.0023 (7) −0.0010 (7) 0.0019 (7)
C15 0.070 (2) 0.0313 (13) 0.0339 (14) −0.0014 (13) 0.0207 (14) 0.0006 (12)
C16 0.0417 (15) 0.0264 (13) 0.0415 (15) −0.0077 (11) 0.0041 (12) −0.0096 (11)

Geometric parameters (Å, °)

Mn1—O3 2.1275 (15) C7—H7A 0.9300
Mn1—O3i 2.1275 (15) C8—C13 1.386 (3)
Mn1—O5i 2.1802 (13) C8—C9 1.394 (3)
Mn1—O5 2.1803 (13) C9—C10 1.383 (3)
Mn1—O4 2.2023 (14) C9—H9A 0.9300
Mn1—O4i 2.2023 (14) C10—C11 1.387 (3)
O1—C1 1.354 (3) C10—H10A 0.9300
O1—H1A 0.8500 C11—C12 1.389 (3)
O2—C14 1.258 (2) C11—C14 1.496 (3)
O3—C14 1.263 (2) C12—C13 1.372 (3)
N1—C7 1.275 (3) C12—H12A 0.9300
N1—C8 1.415 (3) C13—H13A 0.9300
C1—C2 1.386 (3) O4—C15 1.418 (3)
C1—C6 1.414 (3) O4—H4B 0.8500
C2—C3 1.382 (3) O5—C16 1.428 (2)
C2—H2A 0.9300 O5—H5B 0.8500
C3—C4 1.369 (3) C15—H15A 0.9600
C3—H3A 0.9300 C15—H15B 0.9600
C4—C5 1.376 (3) C15—H15C 0.9600
C4—H4A 0.9300 C16—H16A 0.9600
C5—C6 1.383 (3) C16—H16B 0.9600
C5—H5A 0.9300 C16—H16C 0.9600
C6—C7 1.452 (3)
O3—Mn1—O3i 180.00 (10) C13—C8—C9 119.0 (2)
O3—Mn1—O5i 91.39 (5) C13—C8—N1 116.85 (19)
O3i—Mn1—O5i 88.61 (5) C9—C8—N1 124.0 (2)
O3—Mn1—O5 88.61 (5) C10—C9—C8 120.0 (2)
O3i—Mn1—O5 91.39 (5) C10—C9—H9A 120.0
O5i—Mn1—O5 180.00 (7) C8—C9—H9A 120.0
O3—Mn1—O4 89.34 (6) C9—C10—C11 121.0 (2)
O3i—Mn1—O4 90.66 (6) C9—C10—H10A 119.5
O5i—Mn1—O4 92.04 (5) C11—C10—H10A 119.5
O5—Mn1—O4 87.96 (5) C10—C11—C12 118.4 (2)
O3—Mn1—O4i 90.66 (6) C10—C11—C14 121.60 (19)
O3i—Mn1—O4i 89.34 (6) C12—C11—C14 120.02 (19)
O5i—Mn1—O4i 87.96 (5) C13—C12—C11 121.1 (2)
O5—Mn1—O4i 92.04 (5) C13—C12—H12A 119.4
O4—Mn1—O4i 180.00 (7) C11—C12—H12A 119.4
C1—O1—H1A 104.9 C12—C13—C8 120.5 (2)
C14—O3—Mn1 132.05 (14) C12—C13—H13A 119.7
C7—N1—C8 121.23 (19) C8—C13—H13A 119.7
O1—C1—C2 118.8 (2) O2—C14—O3 123.5 (2)
O1—C1—C6 121.2 (2) O2—C14—C11 119.14 (19)
C2—C1—C6 120.0 (2) O3—C14—C11 117.32 (18)
C3—C2—C1 119.3 (2) C15—O4—Mn1 123.20 (14)
C3—C2—H2A 120.4 C15—O4—H4B 109.7
C1—C2—H2A 120.4 Mn1—O4—H4B 109.9
C4—C3—C2 121.6 (2) C16—O5—Mn1 127.52 (13)
C4—C3—H3A 119.2 C16—O5—H5B 106.9
C2—C3—H3A 119.2 Mn1—O5—H5B 106.9
C3—C4—C5 119.2 (2) O4—C15—H15A 109.5
C3—C4—H4A 120.4 O4—C15—H15B 109.5
C5—C4—H4A 120.4 H15A—C15—H15B 109.5
C4—C5—C6 121.6 (2) O4—C15—H15C 109.5
C4—C5—H5A 119.2 H15A—C15—H15C 109.5
C6—C5—H5A 119.2 H15B—C15—H15C 109.5
C5—C6—C1 118.4 (2) O5—C16—H16A 109.5
C5—C6—C7 120.2 (2) O5—C16—H16B 109.5
C1—C6—C7 121.4 (2) H16A—C16—H16B 109.5
N1—C7—C6 122.4 (2) O5—C16—H16C 109.5
N1—C7—H7A 118.8 H16A—C16—H16C 109.5
C6—C7—H7A 118.8 H16B—C16—H16C 109.5
O5i—Mn1—O3—C14 −173.33 (18) C8—C9—C10—C11 1.0 (3)
O5—Mn1—O3—C14 6.67 (18) C9—C10—C11—C12 0.3 (3)
O4—Mn1—O3—C14 94.64 (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—C3 178.3 (2) C14—C11—C12—C13 179.17 (18)
C6—C1—C2—C3 −0.6 (3) C11—C12—C13—C8 0.4 (3)
C1—C2—C3—C4 −0.5 (4) C9—C8—C13—C12 0.8 (3)
C2—C3—C4—C5 1.0 (4) N1—C8—C13—C12 176.55 (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—C7 176.7 (2) C10—C11—C14—O2 10.7 (3)
O1—C1—C6—C5 −177.6 (2) C12—C11—C14—O2 −169.4 (2)
C2—C1—C6—C5 1.3 (3) C10—C11—C14—O3 −170.6 (2)
O1—C1—C6—C7 4.8 (3) C12—C11—C14—O3 9.2 (3)
C2—C1—C6—C7 −176.2 (2) O3—Mn1—O4—C15 −41.12 (17)
C8—N1—C7—C6 174.53 (19) O3i—Mn1—O4—C15 138.88 (17)
C5—C6—C7—N1 −174.7 (2) O5i—Mn1—O4—C15 −132.49 (17)
C1—C6—C7—N1 2.8 (3) O5—Mn1—O4—C15 47.51 (17)
C7—N1—C8—C13 157.1 (2) O3—Mn1—O5—C16 −142.12 (16)
C7—N1—C8—C9 −27.4 (3) O3i—Mn1—O5—C16 37.88 (16)
C13—C8—C9—C10 −1.5 (3) O4—Mn1—O5—C16 128.49 (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···A D—H H···A D···A D—H···A
O1—H1A···N1 0.85 1.83 2.619 (2) 153
O4—H4B···O2ii 0.85 1.84 2.621 (2) 151
O5—H5B···O2 0.85 1.83 2.618 (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

  1. Deeth, R. J. (2008). Inorg. Chem.47, 6711–6725. [DOI] [PubMed]
  2. Dubois, L., Pécaut, J., Charlot, M.-F., Baffert, C., Collomb, M.-N., Deronzier, A. & Latour, J.-M. (2008). Chem. Eur. J.14, 3013–3025. [DOI] [PubMed]
  3. 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.
  4. 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.
  5. Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Abingdon, England.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-65-0m634-sup1.cif (19.1KB, cif)

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

e-65-0m634-Isup2.hkl (165.5KB, hkl)

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


Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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