Literature DB >> 21589246

Poly[[diaqua-(μ(2)-5,5-dioxodibenzo[b,d]thio-phene-3,7-dicarboxyl-ato)(μ(2)-ethyl-ene glycol)manganese(II)] dimethyl-acetamide solvate].

Xiu-Chun Yi1, Li Yan, En-Qing Gao.   

Abstract

In the title complex, {[Mn(C(14)H(6)O(6)S)(C(2)H(6)O(2))(H(2)O)(2)]·C(4)H(9)NO}(n), the Mn(II) ion is six-coordinated in a trans-octa-hedral geometry by two carboxyl-ate O atoms from two 5,5-dioxodibenzo[b,d]thio-phene-3,7-dicarboxyl-ate (L) ligands in a monodentate mode, two O atoms from two ethyl-ene glycol (EG) mol-ecules and two aqua O atoms. The metal ions are linked by the EG and L ligands, forming two-dimensional coordination networks, which are associated into the three-dimensional structure through O-H⋯O hydrogen bonds.

Entities:  

Year:  2010        PMID: 21589246      PMCID: PMC3011537          DOI: 10.1107/S1600536810045411

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN: 1600-5368


Related literature

For the use of H2 L ligands in the construction of coordination polymers, including metal-organic frameworks with function­alized pores, see: Neofotistou et al. (2010 ▶). Kanaizuka et al. (2010 ▶). Yan et al. (2009 ▶). For the ligand synthesis, see: Neofotistou et al. (2009 ▶).

Experimental

Crystal data

[Mn(C14H6O6S)(C2H6O2)(H2O)2]·C4H9NO M = 542.41 Monoclinic, a = 7.0564 (3) Å b = 11.8142 (4) Å c = 28.0008 (10) Å β = 100.544 (1)° V = 2294.89 (15) Å3 Z = 4 Mo Kα radiation μ = 0.73 mm−1 T = 296 K 0.30 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.811, T max = 0.931 30673 measured reflections 5716 independent reflections 5221 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.083 S = 1.07 5716 reflections 335 parameters 4 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.32 e Å−3 Δρmin = −0.36 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810045411/fk2028sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045411/fk2028Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Mn(C14H6O6S)(C2H6O2)(H2O)2]·C4H9NOF(000) = 1124
Mr = 542.41Dx = 1.570 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9208 reflections
a = 7.0564 (3) Åθ = 2.3–26°
b = 11.8142 (4) ŵ = 0.73 mm1
c = 28.0008 (10) ÅT = 296 K
β = 100.544 (1)°Columnar, colourless
V = 2294.89 (15) Å30.30 × 0.20 × 0.10 mm
Z = 4
Bruker APEXII CCD area-detector diffractometer5716 independent reflections
Radiation source: fine-focus sealed tube5221 reflections with I > 2σ(I)
graphiteRint = 0.025
φ and ω scansθmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −9→7
Tmin = 0.811, Tmax = 0.931k = −15→14
30673 measured reflectionsl = −37→36
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: geom and difmap
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083w = 1/[σ2(Fo2) + (0.0425P)2 + 1.0021P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
5716 reflectionsΔρmax = 0.32 e Å3
335 parametersΔρmin = −0.36 e Å3
4 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0011 (3)
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.
xyzUiso*/Ueq
Mn10.22688 (3)0.673463 (17)0.267191 (7)0.02227 (7)
C10.43784 (19)0.86846 (12)0.33374 (5)0.0236 (3)
C20.53981 (19)0.90349 (12)0.38359 (5)0.0225 (3)
C30.5765 (2)1.01741 (12)0.39461 (5)0.0249 (3)
H3A0.54331.07130.37030.030*
C40.5922 (2)0.82195 (11)0.41959 (5)0.0247 (3)
H4A0.57040.74540.41300.030*
C50.6613 (2)1.05261 (12)0.44092 (5)0.0247 (3)
H5A0.68421.12900.44760.030*
C60.67736 (19)0.85829 (12)0.46533 (5)0.0229 (3)
C70.71153 (19)0.97220 (11)0.47712 (5)0.0216 (2)
C80.79778 (19)0.98999 (11)0.52870 (5)0.0213 (2)
C90.8502 (2)1.09104 (11)0.55269 (5)0.0244 (3)
H9A0.83141.15960.53620.029*
C100.8262 (2)0.88924 (11)0.55495 (5)0.0229 (3)
C110.9316 (2)1.08823 (12)0.60187 (5)0.0242 (3)
H11A0.96871.15570.61800.029*
C120.90422 (19)0.88466 (12)0.60378 (5)0.0235 (3)
H12A0.91990.81610.62030.028*
C130.95877 (18)0.98663 (11)0.62747 (5)0.0215 (3)
C141.05227 (19)0.98394 (12)0.68052 (5)0.0224 (3)
O10.39522 (15)0.76549 (9)0.32753 (4)0.0290 (2)
O20.39864 (18)0.94438 (10)0.30224 (4)0.0366 (3)
O31.05942 (16)0.88879 (9)0.70073 (4)0.0316 (2)
O41.11941 (17)1.07339 (9)0.70058 (4)0.0339 (2)
O50.5980 (2)0.71159 (11)0.53019 (4)0.0437 (3)
O60.92266 (19)0.70701 (10)0.51083 (4)0.0411 (3)
S10.75616 (5)0.77206 (3)0.516692 (12)0.02602 (9)
C15−0.2116 (2)0.65002 (14)0.28938 (6)0.0334 (3)
H15A−0.27800.65710.31670.040*
H15B−0.18880.57020.28470.040*
C16−0.3383 (2)0.69648 (15)0.24442 (6)0.0334 (3)
H16A−0.36290.77610.24900.040*
H16B−0.27300.68940.21690.040*
O7−0.03049 (15)0.70750 (10)0.30054 (4)0.0312 (2)
H7−0.052 (3)0.777 (2)0.3005 (8)0.048 (6)*
O8−0.51664 (16)0.63629 (11)0.23467 (5)0.0381 (3)
H8−0.495 (3)0.5748 (15)0.2233 (8)0.052 (6)*
O90.1821 (2)0.83273 (10)0.23213 (5)0.0471 (3)
H9C0.135 (3)0.854 (2)0.2043 (6)0.056 (7)*
H9B0.246 (3)0.8828 (18)0.2484 (7)0.057 (7)*
O100.24423 (19)0.49977 (10)0.29494 (5)0.0352 (3)
H10C0.182 (3)0.474 (2)0.3150 (9)0.057 (7)*
H10B0.210 (4)0.463 (2)0.2701 (10)0.072 (9)*
C17−0.0751 (4)1.0498 (2)0.08416 (8)0.0639 (6)
H17A−0.18881.05910.09810.096*
H17B−0.11151.02810.05070.096*
H17C−0.00531.11990.08630.096*
C180.0504 (3)0.95932 (15)0.11144 (6)0.0391 (4)
C190.3395 (3)0.8464 (2)0.12584 (8)0.0578 (5)
H19A0.26000.78650.13440.087*
H19B0.41420.87820.15480.087*
H19C0.42440.81680.10570.087*
C200.2899 (5)0.9857 (2)0.05873 (11)0.0830 (9)
H20A0.20251.04370.04430.125*
H20B0.30050.92880.03490.125*
H20C0.41441.01840.07030.125*
O11−0.0072 (2)0.90934 (12)0.14522 (4)0.0461 (3)
N10.2175 (2)0.93427 (13)0.09933 (6)0.0440 (3)
U11U22U33U12U13U23
Mn10.02329 (11)0.02213 (11)0.01900 (11)−0.00047 (7)−0.00245 (8)−0.00162 (7)
C10.0221 (6)0.0278 (7)0.0191 (6)−0.0016 (5)−0.0007 (5)−0.0006 (5)
C20.0211 (6)0.0267 (6)0.0184 (6)−0.0021 (5)0.0002 (5)−0.0018 (5)
C30.0283 (7)0.0253 (7)0.0193 (6)−0.0009 (5)−0.0004 (5)0.0015 (5)
C40.0268 (7)0.0227 (6)0.0228 (6)−0.0024 (5)−0.0006 (5)−0.0026 (5)
C50.0302 (7)0.0217 (6)0.0207 (6)−0.0010 (5)0.0009 (5)−0.0008 (5)
C60.0244 (6)0.0235 (6)0.0190 (6)0.0005 (5)−0.0006 (5)0.0014 (5)
C70.0212 (6)0.0247 (6)0.0177 (6)−0.0004 (5)0.0005 (5)−0.0012 (5)
C80.0216 (6)0.0236 (6)0.0178 (6)0.0000 (5)0.0013 (5)−0.0002 (5)
C90.0301 (7)0.0212 (6)0.0204 (6)0.0001 (5)0.0010 (5)0.0014 (5)
C100.0255 (6)0.0211 (6)0.0206 (6)−0.0014 (5)0.0006 (5)−0.0020 (5)
C110.0276 (6)0.0225 (6)0.0209 (6)−0.0011 (5)0.0004 (5)−0.0026 (5)
C120.0257 (6)0.0231 (6)0.0203 (6)0.0011 (5)0.0003 (5)0.0020 (5)
C130.0203 (6)0.0255 (6)0.0176 (6)0.0015 (5)0.0002 (5)−0.0005 (5)
C140.0213 (6)0.0256 (6)0.0187 (6)0.0031 (5)−0.0004 (5)−0.0007 (5)
O10.0348 (5)0.0260 (5)0.0221 (5)−0.0033 (4)−0.0054 (4)−0.0028 (4)
O20.0494 (7)0.0311 (6)0.0234 (5)−0.0091 (5)−0.0092 (5)0.0045 (4)
O30.0397 (6)0.0270 (5)0.0222 (5)−0.0004 (4)−0.0094 (4)0.0035 (4)
O40.0472 (6)0.0264 (5)0.0234 (5)−0.0010 (5)−0.0062 (4)−0.0033 (4)
O50.0572 (8)0.0372 (6)0.0347 (6)−0.0207 (6)0.0036 (5)0.0026 (5)
O60.0543 (7)0.0313 (6)0.0340 (6)0.0154 (5)−0.0022 (5)−0.0037 (5)
S10.03603 (19)0.01997 (16)0.01953 (16)−0.00206 (13)−0.00157 (13)−0.00020 (11)
C150.0273 (7)0.0319 (7)0.0406 (8)−0.0013 (6)0.0048 (6)0.0038 (6)
C160.0256 (7)0.0369 (8)0.0372 (8)−0.0023 (6)0.0044 (6)−0.0012 (6)
O70.0269 (5)0.0278 (5)0.0375 (6)0.0006 (4)0.0022 (4)−0.0058 (4)
O80.0257 (5)0.0373 (6)0.0516 (7)−0.0023 (5)0.0076 (5)−0.0186 (5)
O90.0779 (10)0.0270 (6)0.0266 (6)−0.0056 (6)−0.0164 (6)0.0035 (5)
O100.0474 (7)0.0284 (6)0.0280 (6)−0.0012 (5)0.0018 (5)0.0029 (5)
C170.0792 (16)0.0631 (14)0.0481 (12)0.0237 (12)0.0083 (11)0.0178 (10)
C180.0535 (10)0.0349 (8)0.0253 (7)0.0019 (7)−0.0021 (7)−0.0032 (6)
C190.0607 (13)0.0621 (13)0.0526 (12)0.0184 (11)0.0155 (10)0.0050 (10)
C200.103 (2)0.0651 (16)0.095 (2)0.0174 (15)0.0574 (18)0.0312 (15)
O110.0525 (8)0.0550 (8)0.0298 (6)0.0113 (6)0.0049 (5)0.0074 (5)
N10.0569 (10)0.0382 (8)0.0377 (8)0.0020 (7)0.0109 (7)−0.0011 (6)
Mn1—O92.1191 (12)C14—O31.2553 (17)
Mn1—O3i2.1437 (10)O3—Mn1iii2.1437 (10)
Mn1—O12.1710 (10)O5—S11.4329 (13)
Mn1—O102.1897 (12)O6—S11.4382 (13)
Mn1—O8ii2.2138 (12)C15—O71.4303 (18)
Mn1—O72.2253 (11)C15—C161.508 (2)
C1—O21.2529 (17)C15—H15A0.9700
C1—O11.2576 (18)C15—H15B0.9700
C1—C21.5066 (18)C16—O81.4275 (19)
C2—C31.3943 (19)C16—H16A0.9700
C2—C41.3945 (19)C16—H16B0.9700
C3—C51.3889 (19)O7—H70.84 (2)
C3—H3A0.9300O8—Mn1iv2.2138 (11)
C4—C61.3799 (18)O8—H80.818 (16)
C4—H4A0.9300O9—H9C0.827 (15)
C5—C71.3871 (18)O9—H9B0.827 (15)
C5—H5A0.9300O10—H10C0.83 (3)
C6—C71.3961 (19)O10—H10B0.82 (3)
C6—S11.7671 (14)C17—C181.504 (3)
C7—C81.4762 (17)C17—H17A0.9600
C8—C91.3864 (18)C17—H17B0.9600
C8—C101.3941 (18)C17—H17C0.9600
C9—C111.3919 (18)C18—O111.245 (2)
C9—H9A0.9300C18—N11.318 (2)
C10—C121.3784 (18)C19—N11.461 (3)
C10—S11.7648 (13)C19—H19A0.9600
C11—C131.3932 (19)C19—H19B0.9600
C11—H11A0.9300C19—H19C0.9600
C12—C131.3950 (19)C20—N11.462 (3)
C12—H12A0.9300C20—H20A0.9600
C13—C141.5114 (17)C20—H20B0.9600
C14—O41.2488 (17)C20—H20C0.9600
O9—Mn1—O3i83.73 (4)C1—O1—Mn1132.45 (9)
O9—Mn1—O185.98 (4)C14—O3—Mn1iii131.98 (9)
O3i—Mn1—O1169.61 (4)O5—S1—O6117.10 (8)
O9—Mn1—O10172.07 (5)O5—S1—C10112.10 (7)
O3i—Mn1—O1088.43 (4)O6—S1—C10110.15 (7)
O1—Mn1—O10101.89 (4)O5—S1—C6110.96 (7)
O9—Mn1—O8ii92.82 (6)O6—S1—C6110.93 (7)
O3i—Mn1—O8ii86.40 (4)C10—S1—C693.06 (6)
O1—Mn1—O8ii92.72 (4)O7—C15—C16112.28 (13)
O10—Mn1—O8ii87.89 (5)O7—C15—H15A109.1
O9—Mn1—O788.29 (6)C16—C15—H15A109.1
O3i—Mn1—O793.65 (4)O7—C15—H15B109.1
O1—Mn1—O787.44 (4)C16—C15—H15B109.1
O10—Mn1—O791.00 (5)H15A—C15—H15B107.9
O8ii—Mn1—O7178.89 (5)O8—C16—C15110.22 (14)
O2—C1—O1125.37 (12)O8—C16—H16A109.6
O2—C1—C2117.52 (12)C15—C16—H16A109.6
O1—C1—C2117.09 (12)O8—C16—H16B109.6
C3—C2—C4119.54 (12)C15—C16—H16B109.6
C3—C2—C1120.53 (12)H16A—C16—H16B108.1
C4—C2—C1119.90 (12)C15—O7—Mn1125.99 (10)
C5—C3—C2121.77 (13)C15—O7—H7108.4 (15)
C5—C3—H3A119.1Mn1—O7—H7109.7 (16)
C2—C3—H3A119.1C16—O8—Mn1iv125.51 (10)
C6—C4—C2117.96 (12)C16—O8—H8107.4 (16)
C6—C4—H4A121.0Mn1iv—O8—H8123.9 (16)
C2—C4—H4A121.0Mn1—O9—H9C134.6 (16)
C7—C5—C3119.08 (13)Mn1—O9—H9B111.1 (16)
C7—C5—H5A120.5H9C—O9—H9B113 (2)
C3—C5—H5A120.5Mn1—O10—H10C125.2 (17)
C4—C6—C7123.13 (12)Mn1—O10—H10B102 (2)
C4—C6—S1126.50 (11)H10C—O10—H10B106 (2)
C7—C6—S1110.38 (10)C18—C17—H17A109.5
C5—C7—C6118.52 (12)C18—C17—H17B109.5
C5—C7—C8128.45 (12)H17A—C17—H17B109.5
C6—C7—C8113.03 (12)C18—C17—H17C109.5
C9—C8—C10118.68 (12)H17A—C17—H17C109.5
C9—C8—C7128.49 (12)H17B—C17—H17C109.5
C10—C8—C7112.83 (12)O11—C18—N1121.38 (16)
C8—C9—C11118.95 (12)O11—C18—C17118.61 (18)
C8—C9—H9A120.5N1—C18—C17120.01 (18)
C11—C9—H9A120.5N1—C19—H19A109.5
C12—C10—C8123.32 (12)N1—C19—H19B109.5
C12—C10—S1126.02 (11)H19A—C19—H19B109.5
C8—C10—S1110.64 (10)N1—C19—H19C109.5
C9—C11—C13121.50 (12)H19A—C19—H19C109.5
C9—C11—H11A119.2H19B—C19—H19C109.5
C13—C11—H11A119.2N1—C20—H20A109.5
C10—C12—C13117.59 (12)N1—C20—H20B109.5
C10—C12—H12A121.2H20A—C20—H20B109.5
C13—C12—H12A121.2N1—C20—H20C109.5
C11—C13—C12119.96 (12)H20A—C20—H20C109.5
C11—C13—C14121.20 (12)H20B—C20—H20C109.5
C12—C13—C14118.82 (12)C18—N1—C19120.01 (16)
O4—C14—O3125.06 (12)C18—N1—C20124.28 (18)
O4—C14—C13119.06 (12)C19—N1—C20115.66 (19)
O3—C14—C13115.87 (12)
D—H···AD—HH···AD···AD—H···A
O7—H7···O4v0.84 (2)1.83 (2)2.6623 (16)175 (2)
O8—H8···O2vi0.82 (2)1.88 (2)2.6865 (16)169 (2)
O9—H9C···O110.83 (2)1.89 (2)2.7086 (17)171 (2)
O9—H9B···O20.83 (2)1.84 (2)2.6135 (16)156 (2)
O10—H10C···O11vi0.83 (3)1.96 (3)2.7877 (19)172 (2)
O10—H10B···O4i0.82 (3)1.98 (3)2.7663 (16)161 (3)
Table 1

Selected bond lengths (Å)

Mn1—O92.1191 (12)
Mn1—O3i2.1437 (10)
Mn1—O12.1710 (10)
Mn1—O102.1897 (12)
Mn1—O8ii2.2138 (12)
Mn1—O72.2253 (11)

Symmetry codes: (i) ; (ii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
O7—H7⋯O4iii0.84 (2)1.83 (2)2.6623 (16)175 (2)
O8—H8⋯O2iv0.82 (2)1.88 (2)2.6865 (16)169 (2)
O9—H9C⋯O110.83 (2)1.89 (2)2.7086 (17)171 (2)
O9—H9B⋯O20.83 (2)1.84 (2)2.6135 (16)156 (2)
O10—H10C⋯O11iv0.83 (3)1.96 (3)2.7877 (19)172 (2)
O10—H10B⋯O4i0.82 (3)1.98 (3)2.7663 (16)161 (3)

Symmetry codes: (i) ; (iii) ; (iv) .

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