Literature DB >> 23468728

Bis(μ-2-carb-oxy-methyl-2-hy-droxy-butane-dioato)bis-[diaqua-manganese(II)]-1,2-bis-(pyridin-4-yl)ethene-water (1/1/2).

In Hong Hwang1, Pan-Gi Kim, Jae-Cheon Lee, Cheal Kim, Youngmee Kim.   

Abstract

The asymmetric unit of the title compound, [Mn2(C6H6O7)2(H2O)4]·C12H10N2·2H2O, contains half of the centrosymmetric Mn complex dimer, half of a 1,2-bis-(pyridin-4-yl)ethene mol-ecule, which lies across an inversion center, and one water mol-ecule. Two citrate ligands bridge two Mn(II) ions, and each Mn(II) atom is coordinated by four O atoms from the citrate ligands (one from hy-droxy and three from carboxyl-ate groups) and two water O atoms, forming a distorted octa-hedral environment. In the crystal, O-H⋯O and O-H⋯N hydrogen bonds link the centrosymmetric dimers and lattice water mol-ecules into a three-dimensional structure which is further stabilized by inter-molecular π-π inter-actions [centroid-centroid distance = 3.959 (2) Å]. Weak C-H⋯O hydrogen bonding interactions are also observed.

Entities:  

Year:  2012        PMID： 23468728      PMCID： PMC3588763          DOI： 10.1107/S1600536812047034

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


Related literature

For inter­actions of metal ions with biologically active mol­ecules, see: Daniele et al. (2008 ▶); Parkin (2004 ▶); Tshuva & Lippard (2004 ▶); Stoumpos et al. (2009 ▶). For manganese citrate and zinc citrate complexes, see: Hwang et al. (2012a ▶,b ▶). For related complexes, see: Yu et al. (2009 ▶); Kim et al. (2011 ▶).

Experimental

Crystal data

[Mn2(C6H6O7)2(H2O)4]·C12H10N2·2H2O M = 780.41 Triclinic, a = 9.3970 (19) Å b = 9.4580 (19) Å c = 10.131 (2) Å α = 70.24 (3)° β = 67.11 (3)° γ = 75.52 (3)° V = 773.3 (3) Å3 Z = 1 Mo Kα radiation μ = 0.91 mm−1 T = 170 K 0.15 × 0.10 × 0.02 mm

Data collection

Bruker SMART CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.876, T max = 0.982 4358 measured reflections 2973 independent reflections 2423 reflections with I > 2σ(I) R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.098 S = 1.08 2973 reflections 241 parameters 8 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.47 e Å−3 Δρmin = −0.63 e Å−3 Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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. Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047034/sj5281sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047034/sj5281Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Mn2(C6H6O7)2(H2O)4]·C12H10N2·2H2OZ = 1
Mr = 780.41F(000) = 402
Triclinic, P1Dx = 1.676 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3970 (19) ÅCell parameters from 11909 reflections
b = 9.4580 (19) Åθ = 2.7–27.6°
c = 10.131 (2) ŵ = 0.91 mm−1
α = 70.24 (3)°T = 170 K
β = 67.11 (3)°Plate, colorless
γ = 75.52 (3)°0.15 × 0.10 × 0.02 mm
V = 773.3 (3) Å3
Bruker SMART CCD diffractometer2973 independent reflections
Radiation source: fine-focus sealed tube2423 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)h = −11→10
Tmin = 0.876, Tmax = 0.982k = −11→10
4358 measured reflectionsl = −12→12
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0538P)2] where P = (Fo2 + 2Fc2)/3
2973 reflections(Δ/σ)max = 0.001
241 parametersΔρmax = 0.47 e Å−3
8 restraintsΔρmin = −0.63 e Å−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
Mn10.59596 (4)0.68914 (4)0.60932 (4)0.01775 (14)
O10.4231 (2)0.51640 (19)0.72246 (19)0.0179 (4)
H1O0.435 (3)0.479 (3)0.652 (2)0.021*
O20.3899 (2)0.79755 (19)0.54416 (19)0.0226 (4)
O30.1299 (2)0.8203 (2)0.6391 (2)0.0306 (5)
O40.4605 (2)0.7549 (2)0.81346 (19)0.0248 (4)
O50.3362 (2)0.6926 (2)1.0561 (2)0.0289 (5)
H5O0.411 (2)0.731 (3)1.055 (3)0.035*
O60.3225 (2)0.4206 (2)0.56485 (19)0.0232 (4)
O70.0686 (2)0.4237 (2)0.6196 (2)0.0335 (5)
O80.7614 (2)0.5543 (2)0.7192 (2)0.0263 (4)
H8A0.8656 (9)0.526 (3)0.669 (3)0.032*
H8B0.736 (3)0.4655 (17)0.794 (2)0.032*
O90.7071 (2)0.8889 (2)0.5139 (2)0.0311 (5)
H9A0.8153 (4)0.881 (3)0.478 (3)0.037*
H9B0.671 (3)0.9920 (8)0.501 (3)0.037*
C10.2687 (3)0.6001 (3)0.7591 (3)0.0166 (5)
C20.2613 (3)0.7522 (3)0.6372 (3)0.0187 (5)
C30.2331 (3)0.6280 (3)0.9100 (3)0.0209 (6)
H3A0.13280.69570.93200.025*
H3B0.21830.52990.98710.025*
C40.3533 (3)0.6963 (3)0.9249 (3)0.0195 (5)
C50.1477 (3)0.5074 (3)0.7752 (3)0.0184 (5)
H5A0.14110.41990.86420.022*
H5B0.04470.57130.79340.022*
C60.1791 (3)0.4481 (3)0.6430 (3)0.0188 (5)
N110.5629 (3)0.8142 (2)0.0477 (2)0.0236 (5)
C140.6748 (3)0.8996 (3)0.1754 (3)0.0234 (6)
H140.66730.91970.26380.028*
C110.6896 (3)0.8400 (3)−0.0763 (3)0.0257 (6)
H110.69310.8193−0.16300.031*
C120.8134 (3)0.8954 (3)−0.0799 (3)0.0247 (6)
H120.90150.9128−0.16790.030*
C130.8076 (3)0.9261 (3)0.0493 (3)0.0216 (6)
C150.5544 (3)0.8440 (3)0.1713 (3)0.0244 (6)
H150.46410.82670.25720.029*
C160.9369 (3)0.9793 (3)0.0573 (3)0.0246 (6)
H160.92990.98450.15170.030*
O1W0.0209 (3)0.8324 (2)0.4096 (3)0.0387 (5)
H1WA0.030 (4)0.7316 (11)0.412 (4)0.046*
H1WB0.063 (4)0.826 (4)0.481 (3)0.046*
U11U22U33U12U13U23
Mn10.0180 (2)0.0188 (2)0.0175 (2)−0.00517 (15)−0.00514 (16)−0.00525 (16)
O10.0186 (9)0.0177 (9)0.0194 (9)−0.0028 (7)−0.0062 (8)−0.0075 (7)
O20.0221 (10)0.0213 (9)0.0203 (10)−0.0057 (8)−0.0052 (8)−0.0009 (7)
O30.0199 (10)0.0247 (10)0.0401 (12)0.0003 (8)−0.0103 (9)−0.0022 (9)
O40.0250 (10)0.0303 (10)0.0222 (10)−0.0116 (8)−0.0026 (8)−0.0114 (8)
O50.0301 (11)0.0424 (12)0.0210 (10)−0.0210 (9)−0.0075 (9)−0.0063 (9)
O60.0178 (9)0.0307 (10)0.0245 (10)−0.0041 (8)−0.0045 (8)−0.0140 (8)
O70.0228 (11)0.0514 (13)0.0378 (12)−0.0080 (9)−0.0096 (9)−0.0246 (10)
O80.0207 (10)0.0309 (11)0.0215 (10)−0.0038 (8)−0.0063 (8)−0.0008 (8)
O90.0248 (11)0.0189 (10)0.0454 (13)−0.0073 (8)−0.0074 (9)−0.0057 (9)
C10.0137 (12)0.0181 (12)0.0174 (13)−0.0044 (10)−0.0024 (10)−0.0057 (10)
C20.0184 (14)0.0182 (13)0.0219 (14)−0.0024 (11)−0.0080 (11)−0.0071 (11)
C30.0206 (14)0.0245 (14)0.0181 (13)−0.0066 (11)−0.0039 (11)−0.0067 (11)
C40.0196 (13)0.0184 (13)0.0213 (14)−0.0009 (10)−0.0071 (11)−0.0073 (11)
C50.0151 (13)0.0188 (13)0.0196 (13)−0.0048 (10)−0.0021 (10)−0.0056 (10)
C60.0175 (13)0.0183 (13)0.0209 (13)−0.0072 (10)−0.0055 (11)−0.0033 (10)
N110.0260 (13)0.0213 (11)0.0242 (12)−0.0056 (10)−0.0111 (10)−0.0022 (10)
C140.0304 (15)0.0202 (13)0.0228 (14)−0.0049 (11)−0.0129 (12)−0.0040 (11)
C110.0301 (15)0.0269 (15)0.0251 (15)−0.0054 (12)−0.0121 (12)−0.0086 (12)
C120.0240 (15)0.0284 (15)0.0246 (15)−0.0045 (12)−0.0090 (12)−0.0088 (12)
C130.0226 (14)0.0166 (13)0.0289 (15)−0.0038 (11)−0.0126 (12)−0.0048 (11)
C150.0266 (15)0.0223 (14)0.0243 (14)−0.0057 (11)−0.0096 (12)−0.0033 (11)
C160.0301 (16)0.0252 (14)0.0241 (14)−0.0057 (12)−0.0133 (12)−0.0071 (12)
O1W0.0384 (13)0.0336 (12)0.0503 (14)−0.0040 (10)−0.0209 (11)−0.0123 (11)
Mn1—O92.136 (2)C1—C21.554 (3)
Mn1—O6i2.1373 (18)C3—C41.510 (3)
Mn1—O82.163 (2)C3—H3A0.9900
Mn1—O42.1701 (19)C3—H3B0.9900
Mn1—O22.1864 (19)C5—C61.521 (3)
Mn1—O12.288 (2)C5—H5A0.9900
O1—C11.440 (3)C5—H5B0.9900
O1—H1O0.860 (2)N11—C151.342 (3)
O2—C21.278 (3)N11—C111.352 (4)
O3—C21.238 (3)C14—C151.381 (4)
O4—C41.252 (3)C14—C131.397 (4)
O5—C41.264 (3)C14—H140.9500
O5—H5O0.861 (2)C11—C121.373 (4)
O6—C61.282 (3)C11—H110.9500
O6—Mn1i2.1372 (18)C12—C131.412 (4)
O7—C61.239 (3)C12—H120.9500
O8—H8A0.929 (2)C13—C161.465 (4)
O8—H8B0.930 (2)C15—H150.9500
O9—H9A0.930 (2)C16—C16ii1.328 (5)
O9—H9B0.930 (2)C16—H160.9500
C1—C51.532 (3)O1W—H1WA0.930 (2)
C1—C31.533 (3)O1W—H1WB0.930 (2)
O9—Mn1—O6i104.69 (8)C4—C3—H3A108.1
O9—Mn1—O895.79 (8)C1—C3—H3A108.1
O6i—Mn1—O895.74 (7)C4—C3—H3B108.1
O9—Mn1—O491.93 (8)C1—C3—H3B108.1
O6i—Mn1—O4162.66 (7)H3A—C3—H3B107.3
O8—Mn1—O487.30 (8)O4—C4—O5122.9 (2)
O9—Mn1—O294.80 (8)O4—C4—C3121.5 (2)
O6i—Mn1—O289.16 (7)O5—C4—C3115.6 (2)
O8—Mn1—O2166.80 (7)C6—C5—C1115.7 (2)
O4—Mn1—O284.48 (7)C6—C5—H5A108.4
O9—Mn1—O1166.09 (7)C1—C5—H5A108.4
O6i—Mn1—O183.34 (7)C6—C5—H5B108.4
O8—Mn1—O194.66 (7)C1—C5—H5B108.4
O4—Mn1—O179.39 (7)H5A—C5—H5B107.4
O2—Mn1—O173.70 (7)O7—C6—O6123.8 (2)
C1—O1—Mn1107.29 (13)O7—C6—C5119.6 (2)
C1—O1—H1O107.4 (18)O6—C6—C5116.5 (2)
Mn1—O1—H1O103.0 (18)C15—N11—C11120.3 (2)
C2—O2—Mn1115.41 (15)C15—C14—C13119.9 (2)
C4—O4—Mn1130.73 (16)C15—C14—H14120.1
C4—O5—H5O109 (2)C13—C14—H14120.1
C6—O6—Mn1i124.98 (16)N11—C11—C12121.7 (2)
Mn1—O8—H8A123.5 (18)N11—C11—H11119.2
Mn1—O8—H8B120.1 (18)C12—C11—H11119.2
H8A—O8—H8B102 (2)C11—C12—C13119.0 (3)
Mn1—O9—H9A120.1 (18)C11—C12—H12120.5
Mn1—O9—H9B134.0 (19)C13—C12—H12120.5
H9A—O9—H9B106 (3)C14—C13—C12118.2 (2)
O1—C1—C5110.87 (18)C14—C13—C16119.2 (2)
O1—C1—C3106.59 (19)C12—C13—C16122.6 (2)
C5—C1—C3108.3 (2)N11—C15—C14121.0 (3)
O1—C1—C2110.49 (19)N11—C15—H15119.5
C5—C1—C2109.4 (2)C14—C15—H15119.5
C3—C1—C2111.13 (19)C16ii—C16—C13124.9 (3)
O3—C2—O2125.2 (2)C16ii—C16—H16117.5
O3—C2—C1116.8 (2)C13—C16—H16117.5
O2—C2—C1118.0 (2)H1WA—O1W—H1WB103 (3)
C4—C3—C1116.8 (2)
O9—Mn1—O1—C11.5 (4)C3—C1—C2—O2103.5 (2)
O6i—Mn1—O1—C1−124.70 (14)O1—C1—C3—C451.3 (3)
O8—Mn1—O1—C1140.04 (14)C5—C1—C3—C4170.7 (2)
O4—Mn1—O1—C153.67 (14)C2—C1—C3—C4−69.1 (3)
O2—Mn1—O1—C1−33.63 (13)Mn1—O4—C4—O5144.1 (2)
O9—Mn1—O2—C2−144.09 (17)Mn1—O4—C4—C3−37.3 (3)
O6i—Mn1—O2—C2111.24 (17)C1—C3—C4—O413.8 (4)
O8—Mn1—O2—C2−0.8 (4)C1—C3—C4—O5−167.5 (2)
O4—Mn1—O2—C2−52.61 (17)O1—C1—C5—C6−54.3 (3)
O1—Mn1—O2—C227.93 (16)C3—C1—C5—C6−171.0 (2)
O9—Mn1—O4—C4173.5 (2)C2—C1—C5—C667.8 (3)
O6i—Mn1—O4—C49.9 (4)Mn1i—O6—C6—O7−5.4 (4)
O8—Mn1—O4—C4−90.8 (2)Mn1i—O6—C6—C5171.83 (15)
O2—Mn1—O4—C478.9 (2)C1—C5—C6—O7−153.2 (2)
O1—Mn1—O4—C44.5 (2)C1—C5—C6—O629.4 (3)
Mn1—O1—C1—C5156.94 (15)C15—N11—C11—C120.7 (4)
Mn1—O1—C1—C3−85.35 (18)N11—C11—C12—C13−0.1 (4)
Mn1—O1—C1—C235.5 (2)C15—C14—C13—C120.3 (4)
Mn1—O2—C2—O3162.7 (2)C15—C14—C13—C16−177.6 (2)
Mn1—O2—C2—C1−16.8 (3)C11—C12—C13—C14−0.4 (4)
O1—C1—C2—O3165.9 (2)C11—C12—C13—C16177.4 (2)
C5—C1—C2—O343.6 (3)C11—N11—C15—C14−0.8 (4)
C3—C1—C2—O3−76.0 (3)C13—C14—C15—N110.3 (4)
O1—C1—C2—O2−14.6 (3)C14—C13—C16—C16ii−174.0 (3)
C5—C1—C2—O2−136.9 (2)C12—C13—C16—C16ii8.2 (5)
D—H···AD—HH···AD···AD—H···A
C12—H12···O3iii0.952.483.344 (4)151
C11—H11···O4iv0.952.533.143 (3)123
O9—H9B···O3v0.93 (1)2.56 (3)3.113 (3)118 (2)
O9—H9B···O2v0.93 (1)1.88 (1)2.803 (3)175 (3)
O9—H9A···O1Wvi0.93 (1)1.78 (1)2.695 (3)170 (3)
O8—H8B···O5vii0.93 (1)1.78 (1)2.707 (3)173 (3)
O8—H8A···O7vi0.93 (1)1.87 (1)2.769 (3)163 (3)
O5—H5O···N11viii0.86 (1)1.76 (1)2.625 (3)178 (3)
O1W—H1WB···O30.93 (1)1.92 (1)2.843 (3)175 (3)
O1—H1O···O60.86 (1)1.88 (2)2.616 (2)143 (2)
O1W—H1WA···O7ix0.93 (1)2.08 (2)2.891 (3)145 (3)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C12—H12⋯O3i 0.952.483.344 (4)151
C11—H11⋯O4ii 0.952.533.143 (3)123
O9—H9B⋯O3iii 0.93 (1)2.56 (3)3.113 (3)118 (2)
O9—H9B⋯O2iii 0.93 (1)1.88 (1)2.803 (3)175 (3)
O9—H9A⋯O1W iv 0.93 (1)1.78 (1)2.695 (3)170 (3)
O8—H8B⋯O5v 0.93 (1)1.78 (1)2.707 (3)173 (3)
O8—H8A⋯O7iv 0.93 (1)1.87 (1)2.769 (3)163 (3)
O5—H5O⋯N11vi 0.86 (1)1.76 (1)2.625 (3)178 (3)
O1W—H1WB⋯O30.93 (1)1.92 (1)2.843 (3)175 (3)
O1—H1O⋯O60.86 (1)1.88 (2)2.616 (2)143 (2)
O1W—H1WA⋯O7vii 0.93 (1)2.08 (2)2.891 (3)145 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

  8 in total

Review 1.  Synthetic analogues relevant to the structure and function of zinc enzymes.

Authors:  Gerard Parkin
Journal:  Chem Rev       Date:  2004-02       Impact factor: 60.622

Review 2.  Synthetic models for non-heme carboxylate-bridged diiron metalloproteins: strategies and tactics.

Authors:  Edit Y Tshuva; Stephen J Lippard
Journal:  Chem Rev       Date:  2004-02       Impact factor: 60.622

3.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

4.  catena-Poly[[bis-(2-hydr-oxy-2-phenyl-acetato-κO,O)zinc(II)]-μ-1,2-di-4-pyridylethane-κN:N'].

Authors:  Seung Man Yu; Dong Hoon Shin; Pan-Gi Kim; Cheal Kim; Youngmee Kim
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-08-08

5.  A MnII4 cubane and a novel MnII10MnIII4 cluster from the use of di-2-pyridyl ketone in manganese acetate chemistry.

Authors:  Constantinos C Stoumpos; Ian A Gass; Constantinos J Milios; Nikolia Lalioti; Aris Terzis; Guillem Aromí; Simon J Teat; Euan K Brechin; Spyros P Perlepes
Journal:  Dalton Trans       Date:  2008-11-06       Impact factor: 4.390

6.  Poly[[bis-[μ-1,2-bis-(4-pyrid-yl)ethene]bis-(trichloro-acetato)-cadmium(II)] monohydrate].

Authors:  Jin Hoon Kim; Cheal Kim; Youngmee Kim
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-12-04

7.  Bis(μ-3-carb-oxy-2-hy-droxy-propane-1,2-dicarboxyl-ato)bis(diaquazinc)-1,2-bis-(pyridin-4-yl)ethene-water (1/1/2).

Authors:  In Hong Hwang; Pan-Gi Kim; Cheal Kim; Youngmee Kim
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-26

8.  Bis(μ-2-carboxymethyl-2-hydroxy-butane-dioato)bis-[diaqua-manganese(II)]-1,2-bis-(pyridin-4-yl)ethane-water (1/1/2).

Authors:  In Hong Hwang; Pan-Gi Kim; Cheal Kim; Youngmee Kim
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-07-25
  8 in total

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