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

Hao, C.-J.; Cao, Y.-L.

doi:10.1107/S1600536810022300

metal-organic compounds

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Volume 66| Part 7| July 2010| Page m809

doi:10.1107/S1600536810022300

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

Cheng-Jun Hao ^a ^* and Yun-Li Cao ^a

^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 ); Rosi et al. (2003 ).

Experimental

Crystal data

[Mn(H₂O)₆](C₁₆H₁₂O₆)·H₂O
M_r = 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 ) T_min = 0.760, T_max = 0.886
5275 measured reflections
1899 independent reflections
1647 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.140
S = 1.23
1899 reflections
142 parameters
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯O3^iv	0.85	1.99	2.840 (5)	178
O6—H6D⋯O8	0.85	2.19	3.040 (6)	178
O7—H7C⋯O1^v	0.85	1.95	2.799 (5)	180
O7—H7D⋯O2ⁱⁱ	0.85	1.82	2.673 (4)	180
O8—H8C⋯O2^vi	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 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022300/hy2318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810022300/hy2318Isup2.hkl

checkCIF report

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.

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

	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.]
	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)·H₂O	F(000) = 502
M_r = 481.31	D_x = 1.518 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 2215 reflections
a = 6.0803 (6) Å	θ = 2.5–24.0°
b = 20.643 (2) Å	µ = 0.69 mm⁻¹
c = 8.6610 (9) Å	T = 298 K
β = 104.420 (1)°	Block, colorless
V = 1052.84 (19) Å³	0.42 × 0.21 × 0.18 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD diffractometer	1899 independent reflections
Radiation source: fine-focus sealed tube	1647 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→6
T_min = 0.760, T_max = 0.886	k = −24→22
5275 measured reflections	l = −10→9

Refinement top

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.23	w = 1/[σ²(F_o²) + (0.0292P)² + 3.0592P] where P = (F_o² + 2F_c²)/3
1899 reflections	(Δ/σ)_max < 0.001
142 parameters	Δρ_max = 0.84 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

[Mn(H₂O)₆](C₁₆H₁₂O₆)·H₂O	V = 1052.84 (19) Å³
M_r = 481.31	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 6.0803 (6) Å	µ = 0.69 mm⁻¹
b = 20.643 (2) Å	T = 298 K
c = 8.6610 (9) Å	0.42 × 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)
T_min = 0.760, T_max = 0.886	R_int = 0.024
5275 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.23	Δρ_max = 0.84 e Å⁻³
1899 reflections	Δρ_min = −0.33 e Å⁻³
142 parameters

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

	x	y	z	U_iso*/U_eq
Mn1	0.65486 (15)	0.7500	0.46088 (10)	0.0289 (3)
O1	1.0818 (5)	0.64065 (16)	1.2067 (4)	0.0444 (8)
O2	1.3265 (5)	0.64967 (19)	1.0567 (4)	0.0567 (10)
O3	0.6710 (6)	0.42818 (15)	0.5229 (4)	0.0472 (9)
H3	0.7538	0.4103	0.6004	0.071*
O4	0.2836 (6)	0.7500	0.3483 (5)	0.0296 (9)
H4C	0.2168	0.7166	0.3015	0.036*
O5	1.0130 (7)	0.7500	0.5635 (5)	0.0533 (14)
H5C	1.0885	0.7500	0.4931	0.064*
H5D	1.1062	0.7500	0.6548	0.064*
O6	0.5811 (6)	0.67978 (16)	0.6304 (4)	0.0477 (8)
H6C	0.5029	0.6476	0.5861	0.057*
H6D	0.5095	0.6985	0.6904	0.057*
O7	0.6863 (5)	0.67266 (18)	0.2996 (4)	0.0548 (10)
H7C	0.8061	0.6629	0.2710	0.066*
H7D	0.5724	0.6653	0.2220	0.066*
O8	0.3346 (10)	0.7500	0.8464 (6)	0.090 (2)
H8C	0.3323	0.7167	0.9035	0.109*
C1	1.1422 (7)	0.6306 (2)	1.0792 (5)	0.0377 (11)
C2	0.9858 (7)	0.5932 (2)	0.9471 (5)	0.0321 (10)
C3	0.7845 (7)	0.5675 (2)	0.9661 (5)	0.0364 (10)
H3A	0.7415	0.5747	1.0605	0.044*
C4	0.6454 (7)	0.5311 (2)	0.8455 (5)	0.0371 (10)
H4	0.5098	0.5144	0.8597	0.045*
C5	0.7062 (7)	0.5195 (2)	0.7053 (5)	0.0335 (10)
C6	0.9078 (8)	0.5454 (2)	0.6850 (5)	0.0398 (11)
H6	0.9505	0.5381	0.5906	0.048*
C7	1.0457 (7)	0.5820 (2)	0.8053 (5)	0.0387 (11)
H7	1.1802	0.5993	0.7905	0.046*
C8	0.5518 (8)	0.4795 (2)	0.5750 (5)	0.0365 (10)
H8	0.4286	0.4613	0.6160	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0245 (5)	0.0337 (5)	0.0272 (5)	0.000	0.0039 (4)	0.000
O1	0.0364 (17)	0.051 (2)	0.0399 (18)	0.0007 (15)	−0.0016 (14)	−0.0157 (15)
O2	0.0333 (19)	0.078 (3)	0.052 (2)	−0.0144 (18)	−0.0013 (15)	−0.0261 (19)
O3	0.053 (2)	0.0349 (18)	0.0454 (19)	0.0047 (15)	−0.0045 (15)	−0.0064 (15)
O4	0.026 (2)	0.029 (2)	0.031 (2)	0.000	0.0003 (16)	0.000
O5	0.025 (2)	0.100 (4)	0.032 (2)	0.000	0.0016 (19)	0.000
O6	0.058 (2)	0.0403 (19)	0.0434 (19)	−0.0019 (16)	0.0097 (16)	0.0080 (15)
O7	0.0285 (17)	0.078 (3)	0.053 (2)	0.0039 (17)	0.0007 (15)	−0.0328 (19)
O8	0.065 (4)	0.169 (7)	0.037 (3)	0.000	0.012 (3)	0.000
C1	0.030 (2)	0.037 (3)	0.038 (3)	0.009 (2)	−0.0053 (19)	−0.011 (2)
C2	0.028 (2)	0.029 (2)	0.032 (2)	0.0044 (18)	−0.0058 (18)	−0.0058 (18)
C3	0.037 (2)	0.037 (2)	0.032 (2)	−0.001 (2)	0.0018 (18)	−0.0065 (19)
C4	0.033 (2)	0.036 (2)	0.038 (2)	−0.0057 (19)	−0.0007 (19)	−0.003 (2)
C5	0.030 (2)	0.028 (2)	0.035 (2)	0.0017 (18)	−0.0063 (18)	−0.0048 (18)
C6	0.038 (3)	0.044 (3)	0.034 (2)	0.002 (2)	0.0021 (19)	−0.012 (2)
C7	0.027 (2)	0.045 (3)	0.041 (3)	−0.001 (2)	0.0030 (19)	−0.012 (2)
C8	0.037 (2)	0.033 (2)	0.032 (2)	0.001 (2)	−0.0043 (19)	−0.0060 (19)

Geometric parameters (Å, º) top

Mn1—O5	2.137 (4)	O7—H7D	0.8500
Mn1—O7	2.161 (3)	O8—H8C	0.8500
Mn1—O7ⁱ	2.161 (3)	C1—C2	1.506 (6)
Mn1—O6ⁱ	2.187 (3)	C2—C3	1.381 (6)
Mn1—O6	2.187 (3)	C2—C7	1.384 (6)
Mn1—O4	2.225 (4)	C3—C4	1.390 (6)
O1—C1	1.265 (5)	C3—H3A	0.9300
O2—C1	1.248 (6)	C4—C5	1.375 (6)
O3—C8	1.419 (5)	C4—H4	0.9300
O3—H3	0.8200	C5—C6	1.387 (6)
O4—H4C	0.8500	C5—C8	1.520 (6)
O5—H5C	0.8500	C6—C7	1.388 (6)
O5—H5D	0.8500	C6—H6	0.9300
O6—H6C	0.8500	C7—H7	0.9300
O6—H6D	0.8500	C8—C8ⁱⁱ	1.548 (8)
O7—H7C	0.8500	C8—H8	0.9800

O5—Mn1—O7	91.37 (12)	O2—C1—C2	117.7 (4)
O5—Mn1—O7ⁱ	91.37 (12)	O1—C1—C2	118.8 (4)
O7—Mn1—O7ⁱ	95.3 (2)	C3—C2—C7	118.6 (4)
O5—Mn1—O6ⁱ	94.52 (13)	C3—C2—C1	121.1 (4)
O7—Mn1—O6ⁱ	171.61 (14)	C7—C2—C1	120.2 (4)
O7ⁱ—Mn1—O6ⁱ	90.57 (14)	C2—C3—C4	120.6 (4)
O5—Mn1—O6	94.52 (13)	C2—C3—H3A	119.7
O7—Mn1—O6	90.57 (14)	C4—C3—H3A	119.7
O7ⁱ—Mn1—O6	171.61 (14)	C5—C4—C3	120.7 (4)
O6ⁱ—Mn1—O6	83.01 (19)	C5—C4—H4	119.6
O5—Mn1—O4	178.63 (17)	C3—C4—H4	119.6
O7—Mn1—O4	87.71 (11)	C4—C5—C6	119.0 (4)
O7ⁱ—Mn1—O4	87.71 (11)	C4—C5—C8	119.9 (4)
O6ⁱ—Mn1—O4	86.50 (12)	C6—C5—C8	121.1 (4)
O6—Mn1—O4	86.50 (12)	C5—C6—C7	120.1 (4)
C8—O3—H3	109.5	C5—C6—H6	119.9
Mn1—O4—H4C	121.4	C7—C6—H6	119.9
Mn1—O5—H5C	112.2	C2—C7—C6	120.9 (4)
Mn1—O5—H5D	139.5	C2—C7—H7	119.5
H5C—O5—H5D	108.3	C6—C7—H7	119.5
Mn1—O6—H6C	113.5	O3—C8—C5	111.9 (3)
Mn1—O6—H6D	109.4	O3—C8—C8ⁱⁱ	105.9 (4)
H6C—O6—H6D	108.4	C5—C8—C8ⁱⁱ	111.9 (4)
Mn1—O7—H7C	125.7	O3—C8—H8	109.0
Mn1—O7—H7D	117.3	C5—C8—H8	109.0
H7C—O7—H7D	108.4	C8ⁱⁱ—C8—H8	109.0
O2—C1—O1	123.5 (4)

O2—C1—C2—C3	176.5 (4)	C4—C5—C6—C7	0.3 (7)
O1—C1—C2—C3	−3.0 (6)	C8—C5—C6—C7	179.7 (4)
O2—C1—C2—C7	−1.2 (6)	C3—C2—C7—C6	−0.5 (7)
O1—C1—C2—C7	179.3 (4)	C1—C2—C7—C6	177.3 (4)
C7—C2—C3—C4	0.1 (7)	C5—C6—C7—C2	0.3 (7)
C1—C2—C3—C4	−177.6 (4)	C4—C5—C8—O3	−128.0 (4)
C2—C3—C4—C5	0.5 (7)	C6—C5—C8—O3	52.5 (6)
C3—C4—C5—C6	−0.7 (7)	C4—C5—C8—C8ⁱⁱ	113.3 (6)
C3—C4—C5—C8	179.9 (4)	C6—C5—C8—C8ⁱⁱ	−66.1 (6)

Symmetry codes: (i) x, −y+3/2, z; (ii) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱⁱⁱ	0.82	2.02	2.830 (5)	172
O4—H4C···O1^iv	0.85	1.86	2.712 (4)	177
O5—H5C···O4^v	0.85	1.93	2.777 (6)	175
O5—H5D···O8^v	0.85	1.88	2.728 (7)	175
O6—H6C···O3ⁱⁱ	0.85	1.99	2.840 (5)	178
O6—H6D···O8	0.85	2.19	3.040 (6)	178
O7—H7C···O1^vi	0.85	1.95	2.799 (5)	180
O7—H7D···O2^iv	0.85	1.82	2.673 (4)	180
O8—H8C···O2^vii	0.85	1.92	2.767 (5)	172

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+1, −z+2; (iv) x−1, y, z−1; (v) x+1, y, z; (vi) x, y, z−1; (vii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Mn(H₂O)₆](C₁₆H₁₂O₆)·H₂O
M_r	481.31
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	298
a, b, c (Å)	6.0803 (6), 20.643 (2), 8.6610 (9)
β (°)	104.420 (1)
V (Å³)	1052.84 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.42 × 0.21 × 0.18

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.760, 0.886
No. of measured, independent and observed [I > 2σ(I)] reflections	5275, 1899, 1647
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.140, 1.23
No. of reflections	1899
No. of parameters	142
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.82	2.02	2.830 (5)	171.9
O4—H4C···O1ⁱⁱ	0.85	1.86	2.712 (4)	176.9
O5—H5C···O4ⁱⁱⁱ	0.85	1.93	2.777 (6)	175.0
O5—H5D···O8ⁱⁱⁱ	0.85	1.88	2.728 (7)	174.5
O6—H6C···O3^iv	0.85	1.99	2.840 (5)	177.7
O6—H6D···O8	0.85	2.19	3.040 (6)	177.7
O7—H7C···O1^v	0.85	1.95	2.799 (5)	179.7
O7—H7D···O2ⁱⁱ	0.85	1.82	2.673 (4)	179.5
O8—H8C···O2^vi	0.85	1.92	2.767 (5)	171.9

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.

Acknowledgements

The authors acknowledge Pingdingshan University for supporting this work.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Carlucci, L., Ciani, G. & Proserpio, D. M. (2003). Coord. Chem. Rev. 246, 247–289. Web of Science CrossRef CAS Google Scholar
Rosi, 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 Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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