metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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Hexa­aqua­manganese(II) 4,4′-(1,2-dihy­dr­oxy­ethane-1,2-di­yl)dibenzoate monohydrate

aCollege of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467000, People's Republic of China
*Correspondence e-mail: haochengjun2008@163.com

(Received 1 June 2010; accepted 10 June 2010; online 16 June 2010)

In the title compound, [Mn(H2O)6](C16H12O6)·H2O, the [Mn(H2O)6]2+ complex cation lies on a mirror plane, the 4,4′-(1,2-dihy­droxy­ethane-1,2-di­yl)dibenzoate anion is located on an inversion center and the solvent water mol­ecule also lies on a mirror plane. Extensive O—H⋯O hydrogen-bonding inter­actions between the cations, anions and water mol­ecules stabilize the three-dimensional network.

Related literature

For the intriguing architectures and potential applications of polymeric coordination networks, see: Carlucci et al. (2003[Carlucci, L., Ciani, G. & Proserpio, D. M. (2003). Coord. Chem. Rev. 246, 247-289.]); Rosi et al. (2003[Rosi, N. L., Eckert, J., Eddaoudi, M., Vodak, D. T., Kim, J., O'Keeffe, M. & Yaghi, O. M. (2003). Science, 300, 1127-1129.]).

[Scheme 1]

Experimental

Crystal data
  • [Mn(H2O)6](C16H12O6)·H2O

  • Mr = 481.31

  • Monoclinic, P 21 /m

  • a = 6.0803 (6) Å

  • b = 20.643 (2) Å

  • c = 8.6610 (9) Å

  • β = 104.420 (1)°

  • V = 1052.84 (19) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.69 mm−1

  • T = 298 K

  • 0.42 × 0.21 × 0.18 mm

Data collection
  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.760, Tmax = 0.886

  • 5275 measured reflections

  • 1899 independent reflections

  • 1647 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.140

  • S = 1.23

  • 1899 reflections

  • 142 parameters

  • H-atom parameters constrained

  • Δρmax = 0.84 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O1i 0.82 2.02 2.830 (5) 172
O4—H4C⋯O1ii 0.85 1.86 2.712 (4) 177
O5—H5C⋯O4iii 0.85 1.93 2.777 (6) 175
O5—H5D⋯O8iii 0.85 1.88 2.728 (7) 175
O6—H6C⋯O3iv 0.85 1.99 2.840 (5) 178
O6—H6D⋯O8 0.85 2.19 3.040 (6) 178
O7—H7C⋯O1v 0.85 1.95 2.799 (5) 180
O7—H7D⋯O2ii 0.85 1.82 2.673 (4) 180
O8—H8C⋯O2vi 0.85 1.92 2.767 (5) 172
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) x-1, y, z-1; (iii) x+1, y, z; (iv) -x+1, -y+1, -z+1; (v) x, y, z-1; (vi) x-1, y, z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Current interest in polymeric coordination networks is rapidly expanding for their intriguing architectures (Carlucci et al., 2003) and potential applications (Rosi et al., 2003). We have reacted 1,2-bis(4-carboxyphenyl)-1,2-ethanediol with MnCl2 under hydrothermal conditions to obtain the title compound and its structure is reported here.

As illustrated in Fig. 1, the title compound contains one [Mn(H2O)6]2+ complex cation lying on a mirror plan, one 1,2-dihydroxyethane-1,2-bis(4-benzenecarboxylate) anion located on an inversion center and one solvent water molecule lying on a mirror plan. The carboxylate group lies in the plane of the benzene ring as indicated by the O1—C1—C2—C3 and O2—C1—C2—C7 torsion angles of -3.0 (6) and -1.2 (6)°. The benzene ring is nearly planar with maximum deviations from the mean plane being -0.003 (6) Å for C6. The cation, anion and solvent water molecule interact via O—H···O hydrogen bonds, consolidating the three-dimensional network (Fig. 2, Table 1).

Related literature top

For the intriguing architectures and potential applications of polymeric coordination networks, see: Carlucci et al. (2003); Rosi et al. (2003).

Experimental top

A mixture of MnCl2 (0.1 mmol, 0.013 g), 1,2-bis(4-carboxyphenyl)-1,2-ethanediol (0.1 mmol, 0.03 g) and 10 ml of H2O was sealed in a 20 ml Telflon-lined stainless steel vessel and heated at 303 K for 2 d. Colorless crystals were obtained when the solution was cooled to room temperature slowly.

Refinement top

H atoms bound to C atoms were placed at calculated positions and were treated as riding on the parent atoms, with C—H = 0.93 (aromatic) and 0.98 (CH) Å and with Uiso(H) = 1.2Ueq(C). H atoms of hydroxyl group and water molecules were located in a difference Fourier map and refined as riding, with O—H = 0.85 Å and Uiso(H) = 1.2(1.5 for hydroxyl)Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are shown at the 30% probability level. H atoms and water molecule are omitted for clarity. [Symmetry codes: (i) 1-x, 1-y, 1-z; (ii) x, 3/2-y, z.]
[Figure 2] Fig. 2. View of the three-dimensional network constructed by O—H···O hydrogen bonds (dashed lines). H atoms are omitted for clarity.
Hexaaquamanganese(II) 4,4'-(1,2-dihydroxyethane-1,2-diyl)dibenzoate monohydrate top
Crystal data top
[Mn(H2O)6](C16H12O6)·H2OF(000) = 502
Mr = 481.31Dx = 1.518 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 2215 reflections
a = 6.0803 (6) Åθ = 2.5–24.0°
b = 20.643 (2) ŵ = 0.69 mm1
c = 8.6610 (9) ÅT = 298 K
β = 104.420 (1)°Block, colorless
V = 1052.84 (19) Å30.42 × 0.21 × 0.18 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD
diffractometer
1899 independent reflections
Radiation source: fine-focus sealed tube1647 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ϕ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 76
Tmin = 0.760, Tmax = 0.886k = 2422
5275 measured reflectionsl = 109
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.23 w = 1/[σ2(Fo2) + (0.0292P)2 + 3.0592P]
where P = (Fo2 + 2Fc2)/3
1899 reflections(Δ/σ)max < 0.001
142 parametersΔρmax = 0.84 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
[Mn(H2O)6](C16H12O6)·H2OV = 1052.84 (19) Å3
Mr = 481.31Z = 2
Monoclinic, P21/mMo Kα radiation
a = 6.0803 (6) ŵ = 0.69 mm1
b = 20.643 (2) ÅT = 298 K
c = 8.6610 (9) Å0.42 × 0.21 × 0.18 mm
β = 104.420 (1)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
1899 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1647 reflections with I > 2σ(I)
Tmin = 0.760, Tmax = 0.886Rint = 0.024
5275 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.23Δρmax = 0.84 e Å3
1899 reflectionsΔρmin = 0.33 e Å3
142 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.65486 (15)0.75000.46088 (10)0.0289 (3)
O11.0818 (5)0.64065 (16)1.2067 (4)0.0444 (8)
O21.3265 (5)0.64967 (19)1.0567 (4)0.0567 (10)
O30.6710 (6)0.42818 (15)0.5229 (4)0.0472 (9)
H30.75380.41030.60040.071*
O40.2836 (6)0.75000.3483 (5)0.0296 (9)
H4C0.21680.71660.30150.036*
O51.0130 (7)0.75000.5635 (5)0.0533 (14)
H5C1.08850.75000.49310.064*
H5D1.10620.75000.65480.064*
O60.5811 (6)0.67978 (16)0.6304 (4)0.0477 (8)
H6C0.50290.64760.58610.057*
H6D0.50950.69850.69040.057*
O70.6863 (5)0.67266 (18)0.2996 (4)0.0548 (10)
H7C0.80610.66290.27100.066*
H7D0.57240.66530.22200.066*
O80.3346 (10)0.75000.8464 (6)0.090 (2)
H8C0.33230.71670.90350.109*
C11.1422 (7)0.6306 (2)1.0792 (5)0.0377 (11)
C20.9858 (7)0.5932 (2)0.9471 (5)0.0321 (10)
C30.7845 (7)0.5675 (2)0.9661 (5)0.0364 (10)
H3A0.74150.57471.06050.044*
C40.6454 (7)0.5311 (2)0.8455 (5)0.0371 (10)
H40.50980.51440.85970.045*
C50.7062 (7)0.5195 (2)0.7053 (5)0.0335 (10)
C60.9078 (8)0.5454 (2)0.6850 (5)0.0398 (11)
H60.95050.53810.59060.048*
C71.0457 (7)0.5820 (2)0.8053 (5)0.0387 (11)
H71.18020.59930.79050.046*
C80.5518 (8)0.4795 (2)0.5750 (5)0.0365 (10)
H80.42860.46130.61600.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0245 (5)0.0337 (5)0.0272 (5)0.0000.0039 (4)0.000
O10.0364 (17)0.051 (2)0.0399 (18)0.0007 (15)0.0016 (14)0.0157 (15)
O20.0333 (19)0.078 (3)0.052 (2)0.0144 (18)0.0013 (15)0.0261 (19)
O30.053 (2)0.0349 (18)0.0454 (19)0.0047 (15)0.0045 (15)0.0064 (15)
O40.026 (2)0.029 (2)0.031 (2)0.0000.0003 (16)0.000
O50.025 (2)0.100 (4)0.032 (2)0.0000.0016 (19)0.000
O60.058 (2)0.0403 (19)0.0434 (19)0.0019 (16)0.0097 (16)0.0080 (15)
O70.0285 (17)0.078 (3)0.053 (2)0.0039 (17)0.0007 (15)0.0328 (19)
O80.065 (4)0.169 (7)0.037 (3)0.0000.012 (3)0.000
C10.030 (2)0.037 (3)0.038 (3)0.009 (2)0.0053 (19)0.011 (2)
C20.028 (2)0.029 (2)0.032 (2)0.0044 (18)0.0058 (18)0.0058 (18)
C30.037 (2)0.037 (2)0.032 (2)0.001 (2)0.0018 (18)0.0065 (19)
C40.033 (2)0.036 (2)0.038 (2)0.0057 (19)0.0007 (19)0.003 (2)
C50.030 (2)0.028 (2)0.035 (2)0.0017 (18)0.0063 (18)0.0048 (18)
C60.038 (3)0.044 (3)0.034 (2)0.002 (2)0.0021 (19)0.012 (2)
C70.027 (2)0.045 (3)0.041 (3)0.001 (2)0.0030 (19)0.012 (2)
C80.037 (2)0.033 (2)0.032 (2)0.001 (2)0.0043 (19)0.0060 (19)
Geometric parameters (Å, º) top
Mn1—O52.137 (4)O7—H7D0.8500
Mn1—O72.161 (3)O8—H8C0.8500
Mn1—O7i2.161 (3)C1—C21.506 (6)
Mn1—O6i2.187 (3)C2—C31.381 (6)
Mn1—O62.187 (3)C2—C71.384 (6)
Mn1—O42.225 (4)C3—C41.390 (6)
O1—C11.265 (5)C3—H3A0.9300
O2—C11.248 (6)C4—C51.375 (6)
O3—C81.419 (5)C4—H40.9300
O3—H30.8200C5—C61.387 (6)
O4—H4C0.8500C5—C81.520 (6)
O5—H5C0.8500C6—C71.388 (6)
O5—H5D0.8500C6—H60.9300
O6—H6C0.8500C7—H70.9300
O6—H6D0.8500C8—C8ii1.548 (8)
O7—H7C0.8500C8—H80.9800
O5—Mn1—O791.37 (12)O2—C1—C2117.7 (4)
O5—Mn1—O7i91.37 (12)O1—C1—C2118.8 (4)
O7—Mn1—O7i95.3 (2)C3—C2—C7118.6 (4)
O5—Mn1—O6i94.52 (13)C3—C2—C1121.1 (4)
O7—Mn1—O6i171.61 (14)C7—C2—C1120.2 (4)
O7i—Mn1—O6i90.57 (14)C2—C3—C4120.6 (4)
O5—Mn1—O694.52 (13)C2—C3—H3A119.7
O7—Mn1—O690.57 (14)C4—C3—H3A119.7
O7i—Mn1—O6171.61 (14)C5—C4—C3120.7 (4)
O6i—Mn1—O683.01 (19)C5—C4—H4119.6
O5—Mn1—O4178.63 (17)C3—C4—H4119.6
O7—Mn1—O487.71 (11)C4—C5—C6119.0 (4)
O7i—Mn1—O487.71 (11)C4—C5—C8119.9 (4)
O6i—Mn1—O486.50 (12)C6—C5—C8121.1 (4)
O6—Mn1—O486.50 (12)C5—C6—C7120.1 (4)
C8—O3—H3109.5C5—C6—H6119.9
Mn1—O4—H4C121.4C7—C6—H6119.9
Mn1—O5—H5C112.2C2—C7—C6120.9 (4)
Mn1—O5—H5D139.5C2—C7—H7119.5
H5C—O5—H5D108.3C6—C7—H7119.5
Mn1—O6—H6C113.5O3—C8—C5111.9 (3)
Mn1—O6—H6D109.4O3—C8—C8ii105.9 (4)
H6C—O6—H6D108.4C5—C8—C8ii111.9 (4)
Mn1—O7—H7C125.7O3—C8—H8109.0
Mn1—O7—H7D117.3C5—C8—H8109.0
H7C—O7—H7D108.4C8ii—C8—H8109.0
O2—C1—O1123.5 (4)
O2—C1—C2—C3176.5 (4)C4—C5—C6—C70.3 (7)
O1—C1—C2—C33.0 (6)C8—C5—C6—C7179.7 (4)
O2—C1—C2—C71.2 (6)C3—C2—C7—C60.5 (7)
O1—C1—C2—C7179.3 (4)C1—C2—C7—C6177.3 (4)
C7—C2—C3—C40.1 (7)C5—C6—C7—C20.3 (7)
C1—C2—C3—C4177.6 (4)C4—C5—C8—O3128.0 (4)
C2—C3—C4—C50.5 (7)C6—C5—C8—O352.5 (6)
C3—C4—C5—C60.7 (7)C4—C5—C8—C8ii113.3 (6)
C3—C4—C5—C8179.9 (4)C6—C5—C8—C8ii66.1 (6)
Symmetry codes: (i) x, y+3/2, z; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1iii0.822.022.830 (5)172
O4—H4C···O1iv0.851.862.712 (4)177
O5—H5C···O4v0.851.932.777 (6)175
O5—H5D···O8v0.851.882.728 (7)175
O6—H6C···O3ii0.851.992.840 (5)178
O6—H6D···O80.852.193.040 (6)178
O7—H7C···O1vi0.851.952.799 (5)180
O7—H7D···O2iv0.851.822.673 (4)180
O8—H8C···O2vii0.851.922.767 (5)172
Symmetry codes: (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+2; (iv) x1, y, z1; (v) x+1, y, z; (vi) x, y, z1; (vii) x1, y, z.

Experimental details

Crystal data
Chemical formula[Mn(H2O)6](C16H12O6)·H2O
Mr481.31
Crystal system, space groupMonoclinic, P21/m
Temperature (K)298
a, b, c (Å)6.0803 (6), 20.643 (2), 8.6610 (9)
β (°) 104.420 (1)
V3)1052.84 (19)
Z2
Radiation typeMo Kα
µ (mm1)0.69
Crystal size (mm)0.42 × 0.21 × 0.18
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.760, 0.886
No. of measured, independent and
observed [I > 2σ(I)] reflections
5275, 1899, 1647
Rint0.024
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.140, 1.23
No. of reflections1899
No. of parameters142
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.84, 0.33

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.822.022.830 (5)171.9
O4—H4C···O1ii0.851.862.712 (4)176.9
O5—H5C···O4iii0.851.932.777 (6)175.0
O5—H5D···O8iii0.851.882.728 (7)174.5
O6—H6C···O3iv0.851.992.840 (5)177.7
O6—H6D···O80.852.193.040 (6)177.7
O7—H7C···O1v0.851.952.799 (5)179.7
O7—H7D···O2ii0.851.822.673 (4)179.5
O8—H8C···O2vi0.851.922.767 (5)171.9
Symmetry codes: (i) x+2, y+1, z+2; (ii) x1, y, z1; (iii) x+1, y, z; (iv) x+1, y+1, z+1; (v) x, y, z1; (vi) x1, y, z.
 

Acknowledgements

The authors acknowledge Pingdingshan University for supporting this work.

References

First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCarlucci, L., Ciani, G. & Proserpio, D. M. (2003). Coord. Chem. Rev. 246, 247–289.  Web of Science CrossRef CAS
First citationRosi, N. L., Eckert, J., Eddaoudi, M., Vodak, D. T., Kim, J., O'Keeffe, M. & Yaghi, O. M. (2003). Science, 300, 1127–1129.  Web of Science CrossRef PubMed CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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