Poly[hexa­aqua­(μ9-cyclo­hexane-1,2,3,4,5,6-hexa­carboxyl­ato)trimanganese(II)]

Sun, W.; Zang, H.; Quan, C.

doi:10.1107/S1600536813015626

metal-organic compounds

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Volume 69| Part 7| July 2013| Page m384

https://doi.org/10.1107/S1600536813015626

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Poly[hexaaqua(μ₉-cyclohexane-1,2,3,4,5,6-hexacarboxylato)trimanganese(II)]

Weixuan Sun,^a Hu Zang ^b and Chengshi Quan ^c ^*

^aThe Class 10, 2011, Norman Bethune College of Medicine, Jilin University, 828 Xinmin Street, Changchun 130021, Jilin Province, People's Republic of China, ^bDepartment of Orthopedics, The China–Japan Union Hospital of Jilin University, Changchun 130021, Jilin Province, People's Republic of China, and ^cLaboratory Teaching of Pathology, Norman Bethune College of Medicine, Jilin University, 828 Xinmin Street, Changchun 130021, Jilin Province, People's Republic of China
^*Correspondence e-mail: quanchengshi66@163.com

(Received 10 May 2013; accepted 5 June 2013; online 15 June 2013)

The asymmetric unit of the title compound, [Mn₃(C₁₂H₆O₁₂)(H₂O)₆]_n, comprises one Mn^II ion, one third of a cyclohexane-1,2,3,4,5,6-hexacarboxylate anion and two aqua ligands. The anion is completed by application of a -3 axis. The Mn^II ion is six-coordinated by six O atoms from two aqua ligands and three different cyclohexacarboxylate anions in an octahedral geometry. The six carboxylate groups adopt a bridging bidentate mode to ligate the Mn^II ions. Thus, each cyclohexane-1,2,3,4,5,6-hexacarboxylate anion adopts a μ₉-connected mode, ligating nine different Mn^II ions and forming a three-dimensional framework. In the framework, there are strong O—H⋯O hydrogen-bonding interactions, which further stabilize the crystal structure.

Related literature

For background to compounds with metal-organic framework structures, see: Wang et al. (2010 ); Bourne et al. (2001 ). For their properties, uses and topologies, see: O'Keeffe et al. (2000 ); Song et al. (2012 ).

Experimental

Crystal data

[Mn₃(C₁₂H₆O₁₂)(H₂O)₆]
M_r = 615.09
Trigonal, $[R \overline 3]$
a = 14.5432 (4) Å
c = 14.9445 (10) Å
V = 2737.4 (2) Å³
Z = 6
Mo Kα radiation
μ = 2.15 mm⁻¹
T = 185 K
0.25 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.616, T_max = 0.725
5063 measured reflections
1200 independent reflections
1098 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.064
S = 1.08
1200 reflections
112 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2W—H2A⋯O2Wⁱ	0.81 (2)	2.31 (2)	3.116 (2)	178 (3)
O2W—H2A⋯O3ⁱⁱ	0.81 (2)	2.56 (3)	2.955 (2)	111 (2)
O1W—H1B⋯O4ⁱⁱⁱ	0.87 (2)	1.92 (2)	2.774 (3)	169 (3)
O1W—H1B⋯O3ⁱⁱⁱ	0.87 (2)	2.52 (3)	2.942 (3)	111 (2)
O2W—H2B⋯O1ⁱⁱ	0.84 (2)	2.06 (2)	2.883 (3)	169 (3)
O1W—H1A⋯O1W^iv	0.84 (2)	2.01 (2)	2.8513 (18)	175 (3)
Symmetry codes: (i) x-y+1, x, -z+1; (ii) $[-y+{\script{4\over 3}}, x-y+{\script{2\over 3}}, z-{\script{1\over 3}}]$ ; (iii) $[x-y+{\script{2\over 3}}, x+{\script{1\over 3}}, -z+{\script{4\over 3}}]$ ; (iv) $[y-{\script{1\over 3}}, -x+y+{\script{1\over 3}}, -z+{\script{4\over 3}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813015626/bx2441sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813015626/bx2441Isup2.hkl

checkCIF report

Comment top

Metal-organic frameworks (MOFs) are an emerging class of periodic crystalline solid-state materials constructed from metal ions or polynuclear metal-oxygen clusters and multidentate organic ligands (Wang et al. 2010; Bourne et al. 2001). The potential applications in the realm of catalysis, gas separation, luminescence, as well as their intriguing nature of molecular architectures and topologies make so many chemists devote themselves to this active area (O'Keeffe et al. 2000; Song et al. 2012). The nature of the organic ligand has thus played an important role in designing special metal-organic frameworks. Herein, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride was oxidized and hydrolyzed to give cyclohexacarboxylate anion in situ, which exhibits strong coordination ability to ligate the metal atoms.

In this paper, we describe synthesis and the crystal structure of novel three-dimensional Mn^II-organic compound bearing the ligand 1,2,3,4,5,6-cyclohexacarboxylic acid. X-ray diffraction analysis reveals that the title compound crystallizes in the space group R-3. The asymmetric unit contains one crystallographically unique manganese(II) ion, one third cyclohexacarboxylate anion and two aqua ligands (Fig. 1). The central Mn^II ion exhibits the octahedral coordination geometry by six oxygen atoms from aqua ligands and different cyclohexacarboxylate anions. The whole framework composed of Mn ions and cyclohexacarboxylate anions is further stabilized by abundant and strong hydrogen bonding interactions (Fig. 2). The hydrogen bonding parameters are listed in Table 1.

Related literature top

For the background to metal-organic frameworks see: Wang et al. (2010); Bourne et al. (2001). For their properties, uses and topologies, see: O'Keeffe et al. (2000); Song et al. (2012).

Experimental top

A mixture of bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride (0.1 mmol, 0.025 g), manganese chloride tetrahydrate (0.1 mmol, 0.02 g) were mixed with deionized water (6 ml) in a 15 ml Teflon-lined reactor, and heated at constant 433 K for 3 d. Then, the mixture was cooled to room temperature at a rate of 5 K h-1. Finally, needle-like crystals were obtained in 27% yield based on MnCl₂.

Structure description top

For the background to metal-organic frameworks see: Wang et al. (2010); Bourne et al. (2001). For their properties, uses and topologies, see: O'Keeffe et al. (2000); Song et al. (2012).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecule of (I). Displacement ellipsoids are drawn at the 30% probability level. (i = 1 - x + y,1 - x,z; ii = 1 - x,x-y,z; iii = 1 - x,1 - y,1 - z; iv = y,1 - x + y,1 - z; v = 2/3 + x-y,1/3 + x,4/3 - z)
	Fig. 2. A view along the c axis of the crystal packing of the title compound, hydrogen bonding interactions (dashed lines) in the whole three-dimensional framework.

Poly[hexaaqua(µ₉-cyclohexane-1,2,3,4,5,6-hexacarboxylato)trimanganese(II)] top

Crystal data top

[Mn₃(C₁₂H₆O₁₂)(H₂O)₆]	D_x = 2.239 Mg m⁻³
M_r = 615.09	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 11080 reflections
Hall symbol: -R 3	θ = 1.0–25.0°
a = 14.5432 (4) Å	µ = 2.15 mm⁻¹
c = 14.9445 (10) Å	T = 185 K
V = 2737.4 (2) Å³	Needle, colorless
Z = 6	0.25 × 0.18 × 0.16 mm
F(000) = 1854

Data collection top

Bruker APEXII CCD diffractometer	1200 independent reflections
Radiation source: fine-focus sealed tube	1098 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
φ and ω scans	θ_max = 26.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −17→17
T_min = 0.616, T_max = 0.725	k = −11→17
5063 measured reflections	l = −18→18

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0259P)² + 11.1009P] where P = (F_o² + 2F_c²)/3
1200 reflections	(Δ/σ)_max = 0.001
112 parameters	Δρ_max = 0.75 e Å⁻³
4 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Mn₃(C₁₂H₆O₁₂)(H₂O)₆]	Z = 6
M_r = 615.09	Mo Kα radiation
Trigonal, R3	µ = 2.15 mm⁻¹
a = 14.5432 (4) Å	T = 185 K
c = 14.9445 (10) Å	0.25 × 0.18 × 0.16 mm
V = 2737.4 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	1200 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1098 reflections with I > 2σ(I)
T_min = 0.616, T_max = 0.725	R_int = 0.025
5063 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	4 restraints
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0259P)² + 11.1009P] where P = (F_o² + 2F_c²)/3
1200 reflections	Δρ_max = 0.75 e Å⁻³
112 parameters	Δρ_min = −0.28 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.72468 (17)	0.55633 (17)	0.56658 (15)	0.0119 (5)
C2	0.69763 (17)	0.44523 (17)	0.59739 (16)	0.0124 (5)
H2	0.6975	0.4445	0.6643	0.015*
C3	0.58420 (17)	0.36429 (17)	0.56474 (16)	0.0126 (5)
H3	0.5819	0.3650	0.4979	0.015*
C4	0.50129 (18)	0.38891 (17)	0.60281 (16)	0.0139 (5)
O1	0.68842 (14)	0.60269 (13)	0.61426 (11)	0.0181 (4)
O2	0.77520 (13)	0.59359 (13)	0.49548 (12)	0.0180 (4)
O1W	0.53786 (15)	0.68488 (15)	0.66743 (13)	0.0228 (4)
O3	0.50339 (13)	0.40393 (14)	0.68557 (11)	0.0190 (4)
O2W	0.78828 (15)	0.80851 (14)	0.46574 (12)	0.0211 (4)
O4	0.43295 (13)	0.38944 (13)	0.55035 (11)	0.0187 (4)
Mn1	0.65353 (3)	0.71812 (3)	0.55736 (2)	0.01313 (13)
H2A	0.8391 (18)	0.804 (2)	0.4826 (19)	0.020*
H1B	0.5862 (19)	0.704 (2)	0.7082 (16)	0.020*
H2B	0.775 (2)	0.786 (2)	0.4129 (13)	0.020*
H1A	0.4847 (18)	0.6230 (16)	0.6686 (19)	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0076 (10)	0.0110 (11)	0.0147 (12)	0.0029 (9)	−0.0035 (8)	−0.0014 (9)
C2	0.0108 (11)	0.0094 (11)	0.0169 (12)	0.0050 (9)	0.0007 (9)	−0.0006 (9)
C3	0.0100 (11)	0.0102 (11)	0.0165 (12)	0.0043 (9)	−0.0001 (9)	0.0003 (9)
C4	0.0119 (11)	0.0081 (10)	0.0186 (12)	0.0027 (9)	0.0013 (9)	0.0002 (9)
O1	0.0263 (9)	0.0155 (8)	0.0179 (9)	0.0145 (8)	0.0027 (7)	0.0008 (7)
O2	0.0161 (8)	0.0203 (9)	0.0201 (9)	0.0108 (7)	0.0054 (7)	0.0064 (7)
O1W	0.0189 (9)	0.0241 (10)	0.0229 (10)	0.0089 (8)	0.0011 (8)	0.0057 (8)
O3	0.0166 (8)	0.0255 (9)	0.0154 (9)	0.0109 (8)	0.0008 (7)	−0.0015 (7)
O2W	0.0208 (9)	0.0246 (10)	0.0196 (10)	0.0126 (8)	0.0038 (8)	0.0016 (8)
O4	0.0179 (9)	0.0217 (9)	0.0198 (9)	0.0125 (7)	−0.0066 (7)	−0.0052 (7)
Mn1	0.0142 (2)	0.0124 (2)	0.0134 (2)	0.00709 (15)	−0.00102 (13)	0.00031 (13)

Geometric parameters (Å, º) top

C1—O2	1.251 (3)	O2—Mn1ⁱⁱⁱ	2.1866 (17)
C1—O1	1.263 (3)	O1W—Mn1	2.2263 (19)
C1—C2	1.530 (3)	O1W—H1B	0.866 (17)
C2—C3ⁱ	1.540 (3)	O1W—H1A	0.843 (17)
C2—C3	1.550 (3)	O3—Mn1^iv	2.1581 (17)
C2—H2	1.0000	O2W—Mn1	2.2062 (18)
C3—C4	1.529 (3)	O2W—H2A	0.811 (17)
C3—C2ⁱⁱ	1.540 (3)	O2W—H2B	0.838 (17)
C3—H3	1.0000	O4—Mn1^v	2.1569 (17)
C4—O3	1.254 (3)	Mn1—O4^v	2.1569 (17)
C4—O4	1.269 (3)	Mn1—O3^vi	2.1581 (17)
O1—Mn1	2.1565 (16)	Mn1—O2^vii	2.1866 (17)

O2—C1—O1	124.0 (2)	H1B—O1W—H1A	119 (3)
O2—C1—C2	119.9 (2)	C4—O3—Mn1^iv	131.39 (15)
O1—C1—C2	116.0 (2)	Mn1—O2W—H2A	110 (2)
C1—C2—C3ⁱ	111.91 (18)	Mn1—O2W—H2B	113 (2)
C1—C2—C3	108.74 (18)	H2A—O2W—H2B	108 (3)
C3ⁱ—C2—C3	111.7 (2)	C4—O4—Mn1^v	129.13 (15)
C1—C2—H2	108.1	O1—Mn1—O4^v	90.49 (6)
C3ⁱ—C2—H2	108.1	O1—Mn1—O3^vi	89.74 (7)
C3—C2—H2	108.1	O4^v—Mn1—O3^vi	168.84 (7)
C4—C3—C2ⁱⁱ	107.13 (18)	O1—Mn1—O2^vii	171.49 (7)
C4—C3—C2	111.68 (18)	O4^v—Mn1—O2^vii	86.09 (6)
C2ⁱⁱ—C3—C2	109.3 (2)	O3^vi—Mn1—O2^vii	95.12 (6)
C4—C3—H3	109.6	O1—Mn1—O2W	102.94 (7)
C2ⁱⁱ—C3—H3	109.6	O4^v—Mn1—O2W	89.49 (7)
C2—C3—H3	109.6	O3^vi—Mn1—O2W	79.59 (7)
O3—C4—O4	124.0 (2)	O2^vii—Mn1—O2W	84.84 (7)
O3—C4—C3	117.0 (2)	O1—Mn1—O1W	89.19 (7)
O4—C4—C3	118.9 (2)	O4^v—Mn1—O1W	106.90 (7)
C1—O1—Mn1	121.10 (15)	O3^vi—Mn1—O1W	84.26 (7)
C1—O2—Mn1ⁱⁱⁱ	139.24 (15)	O2^vii—Mn1—O1W	84.36 (7)
Mn1—O1W—H1B	92.6 (19)	O2W—Mn1—O1W	159.65 (7)
Mn1—O1W—H1A	116 (2)

O2—C1—C2—C3ⁱ	28.8 (3)	C2—C1—O1—Mn1	−151.73 (15)
O1—C1—C2—C3ⁱ	−154.7 (2)	O1—C1—O2—Mn1ⁱⁱⁱ	113.2 (2)
O2—C1—C2—C3	−95.1 (2)	C2—C1—O2—Mn1ⁱⁱⁱ	−70.6 (3)
O1—C1—C2—C3	81.4 (2)	O4—C4—O3—Mn1^iv	16.8 (3)
C1—C2—C3—C4	−60.2 (2)	C3—C4—O3—Mn1^iv	−160.75 (15)
C3ⁱ—C2—C3—C4	175.81 (16)	O3—C4—O4—Mn1^v	−136.2 (2)
C1—C2—C3—C2ⁱⁱ	−178.55 (15)	C3—C4—O4—Mn1^v	41.3 (3)
C3ⁱ—C2—C3—C2ⁱⁱ	57.4 (3)	C1—O1—Mn1—O4^v	48.74 (18)
C2ⁱⁱ—C3—C4—O3	69.9 (3)	C1—O1—Mn1—O3^vi	−120.11 (18)
C2—C3—C4—O3	−49.8 (3)	C1—O1—Mn1—O2^vii	115.0 (4)
C2ⁱⁱ—C3—C4—O4	−107.7 (2)	C1—O1—Mn1—O2W	−40.85 (18)
C2—C3—C4—O4	132.6 (2)	C1—O1—Mn1—O1W	155.63 (18)
O2—C1—O1—Mn1	24.6 (3)

Symmetry codes: (i) −x+y+1, −x+1, z; (ii) −y+1, x−y, z; (iii) x−y+1, x, −z+1; (iv) y−1/3, −x+y+1/3, −z+4/3; (v) −x+1, −y+1, −z+1; (vi) x−y+2/3, x+1/3, −z+4/3; (vii) y, −x+y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2A···O2Wⁱⁱⁱ	0.81 (2)	2.31 (2)	3.116 (2)	178 (3)
O2W—H2A···O3^viii	0.81 (2)	2.56 (3)	2.955 (2)	111 (2)
O1W—H1B···O4^vi	0.87 (2)	1.92 (2)	2.774 (3)	169 (3)
O1W—H1B···O3^vi	0.87 (2)	2.52 (3)	2.942 (3)	111 (2)
O2W—H2B···O1^viii	0.84 (2)	2.06 (2)	2.883 (3)	169 (3)
O1W—H1A···O1W^iv	0.84 (2)	2.01 (2)	2.8513 (18)	175 (3)

Symmetry codes: (iii) x−y+1, x, −z+1; (iv) y−1/3, −x+y+1/3, −z+4/3; (vi) x−y+2/3, x+1/3, −z+4/3; (viii) −y+4/3, x−y+2/3, z−1/3.

Experimental details

Crystal data
Chemical formula	[Mn₃(C₁₂H₆O₁₂)(H₂O)₆]
M_r	615.09
Crystal system, space group	Trigonal, R3
Temperature (K)	185
a, c (Å)	14.5432 (4), 14.9445 (10)
V (Å³)	2737.4 (2)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	2.15
Crystal size (mm)	0.25 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.616, 0.725
No. of measured, independent and observed [I > 2σ(I)] reflections	5063, 1200, 1098
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.064, 1.08
No. of reflections	1200
No. of parameters	112
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0259P)² + 11.1009P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), XP in SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2W—H2A···O2Wⁱ	0.811 (17)	2.306 (18)	3.116 (2)	178 (3)
O2W—H2A···O3ⁱⁱ	0.811 (17)	2.56 (3)	2.955 (2)	111 (2)
O1W—H1B···O4ⁱⁱⁱ	0.866 (17)	1.920 (18)	2.774 (3)	169 (3)
O1W—H1B···O3ⁱⁱⁱ	0.866 (17)	2.52 (3)	2.942 (3)	111 (2)
O2W—H2B···O1ⁱⁱ	0.838 (17)	2.057 (18)	2.883 (3)	169 (3)
O1W—H1A···O1W^iv	0.843 (17)	2.010 (18)	2.8513 (18)	175 (3)

Symmetry codes: (i) x−y+1, x, −z+1; (ii) −y+4/3, x−y+2/3, z−1/3; (iii) x−y+2/3, x+1/3, −z+4/3; (iv) y−1/3, −x+y+1/3, −z+4/3.

Acknowledgements

The authors thank Jilin University for supporting this work.

References

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