metal-organic compounds
Bis[4-(2-hydroxybenzylideneamino)benzoato-κO]tetrakis(methanol-κO)manganese(II)
aSchool of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China
*Correspondence e-mail: zhongmin0310@yahoo.com.cn
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 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).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell 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.
Supporting information
10.1107/S160053680901681X/hy2192sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680901681X/hy2192Isup2.hkl
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.
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).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell
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).[Mn(C14H10NO3)2(CH4O)4] | F(000) = 694 |
Mr = 663.57 | Dx = 1.416 Mg m−3 |
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 mm−1 |
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 |
Oxford Diffraction Gemini S Ultra diffractometer | 3374 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2008 reflections with I > 2σ(I) |
Graphite monochromator | 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 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 Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
[Mn(C14H10NO3)2(CH4O)4] | V = 1556.14 (10) Å3 |
Mr = 663.57 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.0341 (6) Å | µ = 0.49 mm−1 |
b = 11.8819 (4) Å | T = 293 K |
c = 8.8178 (3) Å | 0.6 × 0.6 × 0.3 mm |
β = 98.912 (4)° |
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 = 1.000 | Rint = 0.032 |
10167 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 0.92 | Δρmax = 0.55 e Å−3 |
3374 reflections | Δρmin = −0.31 e Å−3 |
205 parameters |
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* |
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) |
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 code: (i) −x+1, −y, −z. |
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 code: (ii) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C14H10NO3)2(CH4O)4] |
Mr | 663.57 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 15.0341 (6), 11.8819 (4), 8.8178 (3) |
β (°) | 98.912 (4) |
V (Å3) | 1556.14 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.49 |
Crystal size (mm) | 0.6 × 0.6 × 0.3 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini S Ultra diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.823, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10167, 3374, 2008 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.102, 0.92 |
No. of reflections | 3374 |
No. of parameters | 205 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.55, −0.31 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).
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···O2i | 0.85 | 1.84 | 2.621 (2) | 151 |
O5—H5B···O2 | 0.85 | 1.83 | 2.618 (2) | 153 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
Acknowledgements
This work was supported by the Natural Science Foundation of Guangxi Province of China (grant No. 0832100).
References
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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).