Diaqua­bis{[1-hydr­oxy-2-(1H-imidazol-3-ium-1-yl)ethane-1,1-di­yl]bis­(hydrogen phospho­nato)}manganese(II)

Zhang, Z.-C.; Li, R.-Q.; Zhang, Y.

doi:10.1107/S160053680905065X

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1701-m1702

doi:10.1107/S160053680905065X

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Diaquabis{[1-hydroxy-2-(1H-imidazol-3-ium-1-yl)ethane-1,1-diyl]bis(hydrogen phosphonato)}manganese(II)

Zai-Chao Zhang,^a ^* Rong-Qing Li ^a and Yu Zhang ^a

^aJiangsu Key Laboratory for the Chemistry of Low-dimensional Materials, Department of Chemistry, Huaiyin Teachers College, 111 West Changjiang Road, Huaian 223300, Jiangsu, People's Republic of China
^*Correspondence e-mail: overloadzz@hotmail.com

(Received 20 November 2009; accepted 24 November 2009; online 28 November 2009)

In the title compound, [Mn(C₅H₉N₂O₇P₂)₂(H₂O)₂], the Mn^II atom (site symmetry $[\overline{1}]$ ) is coordinated by four phosphonate O atoms from a pair of partially deprotonated 1-hydroxy-2-(imidazol-3-yl)ethane-1,1-bisphophonic acid ligands (imhedpH₃⁻) and two water molecules, resulting in a slightly distorted trans-MnO₆ octahedral geometry for the metal ion. In the ligands, the imidazole units are protonated and two of the hydroxy O atoms of the phosphonate groups are deprotonated and chelate the Mn^II, thus forming the neutral molecule of the title compound. The two protonated O atoms within the phosphonate groups of one imhedpH₃⁻ ligand act as hydrogen-bond acceptors for a bifurcated hydrogen bond originating from the coordinated water molecule. The phosphonate units of neigboring molecules are connected with their equivalents in neighboring molecules via two types of inversion-symmetric hydrogen-bonding arrangements with four and two strong O—H⋯O hydrogen bonds, respectively. The two interactions connect molecules into infinite chains along [111] and [110], in combination forming a tightly hydrogen-bonded three-dimensional supramolecular network. This network is further stabilized by additional hydrogen bonds between the protonated imidazole units and one of the coordinated P—O O atoms and by additional O—H⋯O hydrogen bonds between the water molecules and the P=O O atoms of neigboring molecules.

Related literature

For a review of the structures and applications of lanthanide phosphonates, see: Mao (2007 ). For other complexes based on the imhedpH₄ ligand, see: Cao et al. (2007 , 2008 ). For the structures and properties of some metal organophosphonates, see: Rao et al. (2004 ); Yang et al. (2009 ).

Experimental

Crystal data

[Mn(C₅H₉N₂O₇P₂)₂(H₂O)₂]
M_r = 633.14
Triclinic, $[P \overline 1]$
a = 7.4408 (17) Å
b = 8.566 (2) Å
c = 9.680 (2) Å
α = 105.366 (4)°
β = 110.865 (4)°
γ = 97.461 (4)°
V = 538.4 (2) Å³
Z = 1
Mo Kα radiation
μ = 1.00 mm⁻¹
T = 153 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.788, T_max = 0.825
2637 measured reflections
1829 independent reflections
1543 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.135
S = 0.99
1829 reflections
175 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O4ⁱ	0.88	1.85	2.718 (5)	167
O7—H7A⋯O5ⁱⁱ	0.85 (5)	2.07 (5)	2.889 (4)	162 (5)
O6—H6A⋯O5ⁱⁱ	0.84 (5)	1.82 (5)	2.653 (4)	167 (5)
O3—H3A⋯O2ⁱⁱⁱ	0.85 (5)	1.74 (5)	2.573 (4)	167 (5)
O8—H8A⋯O2^iv	0.86 (6)	1.88 (6)	2.707 (5)	162 (5)
O8—H8B⋯O3	0.85 (6)	2.32 (6)	3.042 (5)	143 (5)
O8—H8B⋯O6	0.85 (6)	2.59 (6)	3.124 (5)	122 (5)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y+1, -z; (iv) x-1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680905065X/zl2255sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680905065X/zl2255Isup2.hkl

checkCIF report

Comment top

Organophosphonic acids have attracted much attention in the field of organic-inorganic hybrid materials because of their flexible coordination modes and strong coordination ability (Mao 2007; Rao et. al. 2008; Yang et al. 2009). Compared to other organophosphonic acid derivatives, there are only few complexes of metal-organic compounds with 1-hydroxy-2-(imidazol-3-yl)ethane-1,1-bisphophonic acid (imhedpH₄) and its anions as the ligand (Cao et al. 2007; Cao et al. 2008). Herein, we thus report the synthesis and structure of the title compound, a manganese complex of the monoanion of the aformentioned acid.

The title compound crystallizes in the triclinic system with the space group P1. The Mn^II ion adopts a slightly distorted octahedral geometry and is located on a crystallographic inversion center. Two pairs of phosphonate oxygen atoms (O1, O4, O1ⁱ, O4ⁱ; symmetry code: i, –x, –y, –z) from two equivalent imhedpH₃^- ligands define the equatorial plane, while two equivalent water molecules (O8 and O8ⁱ) occupy the axial sites. The Mn-O bond lengths are in the range of 2.118 (3)-2.218 (3) Å. In the equatorial plane, the O—Mn—O bond angles are 88.35 (11)-91.65 (11)°. The two imhedpH₃^- ligands act as bidentate chelating ligands towards the Mn cation via the two deprotonated phosphonate oxygen atoms O1 and O4, while two of the remaining four phosphonate oxygens are protonated [P1—O3 = 1.565 (3) Å and P2—O6 = 1.572 (3) Å]. These two protonated O atoms O3 and O6 act as a hydrogen bond acceptors for a bifurcated H bond from the coordinated water molecule (O8, see Table 1 for numerical values).

The phosphonate units are connected with their equivalents in neighboring molecules via two types of inversion symmetric hydrogen bonding arrangements (Fig. 2). Phosphonate units of P atom P1 are connecting neighboring molecules along the diagonal of the unit cell by means of four strong O—H···O hydrogen bonds between the P—O—H (O6), C—O—H (O7) and P═O units (O5) of the imhedpH₃^- ligands (Table 1). Dimeric P—O—H···O═P connections are formed between the phosphonate units of P2 in neighboring molecules involving O2 and O3. This second interaction connects molecules along the {1 1 0} direction, and both of these strong hydrogen bonding interactions lead to the formation of infinite chains, and in combination to a tightly hydrogen bonded three-dimensional supramolecular network (Fig. 3). This network is further stabilized by additional hydrogen bonds between the protonated imidazole units towards one of the coordinated P-O oxygen atoms (O4) and by additional O—H···O hydrogen bonds between the water molecule and P═O oxygen atoms (O2) of neigboring molecules (Table 1).

Related literature top

For a review of the structures and applications of lanthanide phosphonates, see: Mao (2007). For other complexes based on the imhedpH₄ ligand, see: Cao et al. (2007, 2008). For the structures and properties of some metal organophosphonates, see: Rao et al. (2004); Yang et al. (2009).

Experimental top

The title compound was prepared by the hydrothermal reaction of a mixture of MnSO₄ (0.1 mmol), imhedpH₄ (0.1 mmol) and H₂O (8.0 mL) in a Teflon-lined stainless steel autoclave (25 ml), which was heated to 413 K for 48 h. Block-shaped light-pink crystals were collected (yield: 48%, based on imhedpH₄). Anal. calcd for C₁₀H₂₂MnN₄O₁₆P₄ (633.13): C 18.97, H 3.50, N 8.85%; found: C 19.06, H 3.71, N 8.90%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular view of the title compound with atomic labeling scheme (50% probability, symmetry code: i, –x, –y, –z).
	Fig. 2. A view of the hydrogen bonding interactions in the structure of the title compound based on its asymmetric unit. Hydrogen bonding interactions within the centrosymmetric units (see comment) are represented by black dashed lines, other as dashed yellow lines (symmetry codes: i, –x, –y, –z; ii, 1–x, 1–y, 1–z; iii, 1–x, 1–y, –z; iv, –1+x, y, z; v, 1+x, y, z; vi, 1–x, –y, 1–z).
	Fig. 3. Packing diagram of the title compound.

Diaquabis{[1-hydroxy-2-(1H-imidazol-3-ium-1-yl)ethane-1,1- diyl]bis(hydrogen phosphonato)}manganese(II) top

Crystal data top

[Mn(C₅H₉N₂O₇P₂)₂(H₂O)₂]	Z = 1
M_r = 633.14	F(000) = 323
Triclinic, P1	D_x = 1.953 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4408 (17) Å	Cell parameters from 584 reflections
b = 8.566 (2) Å	θ = 2.4–24.6°
c = 9.680 (2) Å	µ = 1.00 mm⁻¹
α = 105.366 (4)°	T = 153 K
β = 110.865 (4)°	Block, light pink
γ = 97.461 (4)°	0.25 × 0.20 × 0.20 mm
V = 538.4 (2) Å³

Data collection top

Bruker SMART APEXII diffractometer	1829 independent reflections
Radiation source: fine-focus sealed tube	1543 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→4
T_min = 0.788, T_max = 0.825	k = −10→10
2637 measured reflections	l = −9→11

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0806P)² + 0.0364P] where P = (F_o² + 2F_c²)/3
1829 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Mn(C₅H₉N₂O₇P₂)₂(H₂O)₂]	γ = 97.461 (4)°
M_r = 633.14	V = 538.4 (2) Å³
Triclinic, P1	Z = 1
a = 7.4408 (17) Å	Mo Kα radiation
b = 8.566 (2) Å	µ = 1.00 mm⁻¹
c = 9.680 (2) Å	T = 153 K
α = 105.366 (4)°	0.25 × 0.20 × 0.20 mm
β = 110.865 (4)°

Data collection top

Bruker SMART APEXII diffractometer	1829 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1543 reflections with I > 2σ(I)
T_min = 0.788, T_max = 0.825	R_int = 0.029
2637 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.49 e Å⁻³
1829 reflections	Δρ_min = −0.46 e Å⁻³
175 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.7059 (7)	0.0407 (6)	0.4433 (6)	0.0313 (11)
H1	0.5957	−0.0541	0.3933	0.038*
C2	0.9765 (8)	0.2242 (6)	0.6170 (6)	0.0411 (13)
H2	1.0898	0.2812	0.7125	0.049*
C3	0.9192 (7)	0.2695 (6)	0.4880 (5)	0.0330 (12)
H3	0.9850	0.3632	0.4743	0.040*
C4	0.6265 (7)	0.1604 (6)	0.2269 (5)	0.0263 (10)
H4A	0.5289	0.0511	0.1646	0.032*
H4B	0.7133	0.1768	0.1719	0.032*
C5	0.5147 (6)	0.2977 (5)	0.2313 (5)	0.0186 (9)
Mn1	0.0000	0.0000	0.0000	0.0188 (3)
N1	0.7483 (5)	0.1543 (4)	0.3809 (4)	0.0231 (8)
N2	0.8436 (7)	0.0832 (5)	0.5856 (5)	0.0393 (11)
H2A	0.8485	0.0279	0.6511	0.047*
O1	0.2208 (4)	0.1161 (3)	−0.0561 (3)	0.0218 (7)
O2	0.5292 (4)	0.2914 (3)	−0.0465 (3)	0.0212 (7)
O3	0.2772 (4)	0.4247 (4)	0.0239 (4)	0.0236 (7)
H3A	0.355 (7)	0.511 (6)	0.031 (5)	0.028*
O4	0.1983 (4)	0.1153 (4)	0.2449 (3)	0.0256 (7)
O5	0.4729 (4)	0.3069 (4)	0.5030 (3)	0.0258 (7)
O6	0.2356 (5)	0.4203 (4)	0.3166 (3)	0.0258 (7)
H6A	0.316 (7)	0.515 (6)	0.369 (6)	0.031*
O7	0.6604 (5)	0.4552 (4)	0.3074 (4)	0.0274 (8)
H7A	0.616 (7)	0.534 (6)	0.347 (6)	0.033*
O8	−0.1140 (6)	0.2247 (5)	−0.0097 (5)	0.0421 (10)
H8A	−0.232 (9)	0.226 (7)	−0.018 (7)	0.051*
H8B	−0.021 (9)	0.314 (7)	0.028 (7)	0.051*
P1	0.37848 (16)	0.27554 (13)	0.02248 (13)	0.0187 (3)
P2	0.34950 (16)	0.27977 (13)	0.33400 (12)	0.0203 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.032 (3)	0.032 (3)	0.038 (3)	0.011 (2)	0.017 (2)	0.020 (2)
C2	0.041 (3)	0.036 (3)	0.030 (3)	0.008 (3)	−0.003 (2)	0.011 (2)
C3	0.031 (3)	0.029 (3)	0.030 (3)	0.001 (2)	0.004 (2)	0.011 (2)
C4	0.027 (3)	0.030 (3)	0.020 (2)	0.013 (2)	0.008 (2)	0.006 (2)
C5	0.015 (2)	0.020 (2)	0.016 (2)	0.0023 (18)	0.0028 (18)	0.0052 (17)
Mn1	0.0177 (5)	0.0178 (5)	0.0178 (5)	0.0005 (4)	0.0058 (4)	0.0047 (4)
N1	0.021 (2)	0.025 (2)	0.022 (2)	0.0057 (16)	0.0065 (17)	0.0092 (16)
N2	0.052 (3)	0.045 (3)	0.031 (2)	0.016 (2)	0.017 (2)	0.026 (2)
O1	0.0219 (17)	0.0240 (17)	0.0183 (16)	0.0013 (13)	0.0098 (13)	0.0051 (13)
O2	0.0197 (16)	0.0242 (16)	0.0232 (16)	0.0056 (13)	0.0111 (13)	0.0099 (13)
O3	0.0211 (17)	0.0222 (17)	0.0342 (18)	0.0055 (13)	0.0143 (15)	0.0155 (14)
O4	0.0316 (18)	0.0241 (17)	0.0153 (16)	−0.0009 (14)	0.0062 (14)	0.0061 (13)
O5	0.0251 (17)	0.0299 (18)	0.0168 (16)	0.0001 (14)	0.0063 (14)	0.0057 (13)
O6	0.0223 (18)	0.0273 (18)	0.0225 (17)	0.0041 (14)	0.0080 (14)	0.0027 (14)
O7	0.0222 (17)	0.0244 (18)	0.0294 (18)	0.0004 (14)	0.0095 (15)	0.0035 (14)
O8	0.023 (2)	0.026 (2)	0.077 (3)	0.0073 (16)	0.021 (2)	0.0163 (19)
P1	0.0175 (6)	0.0197 (6)	0.0188 (6)	0.0028 (5)	0.0078 (5)	0.0065 (5)
P2	0.0211 (6)	0.0205 (6)	0.0162 (6)	0.0009 (5)	0.0073 (5)	0.0038 (5)

Geometric parameters (Å, º) top

C1—N2	1.309 (6)	Mn1—O4	2.159 (3)
C1—N1	1.334 (6)	Mn1—O4ⁱ	2.159 (3)
C1—H1	0.9500	Mn1—O8ⁱ	2.213 (4)
C2—N2	1.345 (6)	Mn1—O8	2.213 (4)
C2—C3	1.347 (6)	N2—H2A	0.8800
C2—H2	0.9500	O1—P1	1.489 (3)
C3—N1	1.363 (6)	O2—P1	1.505 (3)
C3—H3	0.9500	O3—P1	1.565 (3)
C4—N1	1.462 (5)	O3—H3A	0.85 (5)
C4—C5	1.526 (6)	O4—P2	1.499 (3)
C4—H4A	0.9900	O5—P2	1.499 (3)
C4—H4B	0.9900	O6—P2	1.571 (3)
C5—O7	1.437 (5)	O6—H6A	0.84 (5)
C5—P2	1.850 (4)	O7—H7A	0.85 (5)
C5—P1	1.854 (4)	O8—H8A	0.86 (6)
Mn1—O1	2.116 (3)	O8—H8B	0.85 (6)
Mn1—O1ⁱ	2.116 (3)

N2—C1—N1	107.7 (4)	O1—Mn1—O8	84.33 (13)
N2—C1—H1	126.2	O1ⁱ—Mn1—O8	95.67 (13)
N1—C1—H1	126.2	O4—Mn1—O8	93.01 (13)
N2—C2—C3	107.3 (4)	O4ⁱ—Mn1—O8	86.99 (13)
N2—C2—H2	126.3	O8ⁱ—Mn1—O8	180.0
C3—C2—H2	126.3	C1—N1—C3	108.7 (4)
C2—C3—N1	106.5 (4)	C1—N1—C4	125.9 (4)
C2—C3—H3	126.8	C3—N1—C4	125.4 (4)
N1—C3—H3	126.8	C1—N2—C2	109.9 (4)
N1—C4—C5	114.6 (3)	C1—N2—H2A	125.1
N1—C4—H4A	108.6	C2—N2—H2A	125.1
C5—C4—H4A	108.6	P1—O1—Mn1	134.48 (17)
N1—C4—H4B	108.6	P1—O3—H3A	111 (3)
C5—C4—H4B	108.6	P2—O4—Mn1	132.06 (17)
H4A—C4—H4B	107.6	P2—O6—H6A	110 (3)
O7—C5—C4	107.3 (3)	C5—O7—H7A	113 (3)
O7—C5—P2	111.1 (3)	Mn1—O8—H8A	121 (4)
C4—C5—P2	112.1 (3)	Mn1—O8—H8B	113 (4)
O7—C5—P1	108.2 (3)	H8A—O8—H8B	123 (5)
C4—C5—P1	104.7 (3)	O1—P1—O2	115.48 (17)
P2—C5—P1	113.0 (2)	O1—P1—O3	108.67 (17)
O1—Mn1—O1ⁱ	180.00 (17)	O2—P1—O3	110.18 (16)
O1—Mn1—O4	88.32 (11)	O1—P1—C5	108.75 (17)
O1ⁱ—Mn1—O4	91.68 (11)	O2—P1—C5	107.50 (18)
O1—Mn1—O4ⁱ	91.68 (11)	O3—P1—C5	105.82 (18)
O1ⁱ—Mn1—O4ⁱ	88.32 (11)	O5—P2—O4	115.53 (17)
O4—Mn1—O4ⁱ	180.00 (17)	O5—P2—O6	111.28 (17)
O1—Mn1—O8ⁱ	95.67 (13)	O4—P2—O6	107.09 (18)
O1ⁱ—Mn1—O8ⁱ	84.33 (13)	O5—P2—C5	109.22 (18)
O4—Mn1—O8ⁱ	86.99 (13)	O4—P2—C5	107.87 (18)
O4ⁱ—Mn1—O8ⁱ	93.01 (13)	O6—P2—C5	105.31 (18)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱⁱ	0.88	1.85	2.718 (5)	167
O7—H7A···O5ⁱⁱⁱ	0.85 (5)	2.07 (5)	2.889 (4)	162 (5)
O6—H6A···O5ⁱⁱⁱ	0.84 (5)	1.82 (5)	2.653 (4)	167 (5)
O3—H3A···O2^iv	0.85 (5)	1.74 (5)	2.573 (4)	167 (5)
O8—H8A···O2^v	0.86 (6)	1.88 (6)	2.707 (5)	162 (5)
O8—H8B···O3	0.85 (6)	2.32 (6)	3.042 (5)	143 (5)
O8—H8B···O6	0.85 (6)	2.59 (6)	3.124 (5)	122 (5)

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

Experimental details

Crystal data
Chemical formula	[Mn(C₅H₉N₂O₇P₂)₂(H₂O)₂]
M_r	633.14
Crystal system, space group	Triclinic, P1
Temperature (K)	153
a, b, c (Å)	7.4408 (17), 8.566 (2), 9.680 (2)
α, β, γ (°)	105.366 (4), 110.865 (4), 97.461 (4)
V (Å³)	538.4 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.00
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.788, 0.825
No. of measured, independent and observed [I > 2σ(I)] reflections	2637, 1829, 1543
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.135, 0.99
No. of reflections	1829
No. of parameters	175
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.46

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O4ⁱ	0.88	1.85	2.718 (5)	167
O7—H7A···O5ⁱⁱ	0.85 (5)	2.07 (5)	2.889 (4)	162 (5)
O6—H6A···O5ⁱⁱ	0.84 (5)	1.82 (5)	2.653 (4)	167 (5)
O3—H3A···O2ⁱⁱⁱ	0.85 (5)	1.74 (5)	2.573 (4)	167 (5)
O8—H8A···O2^iv	0.86 (6)	1.88 (6)	2.707 (5)	162 (5)
O8—H8B···O3	0.85 (6)	2.32 (6)	3.042 (5)	143 (5)
O8—H8B···O6	0.85 (6)	2.59 (6)	3.124 (5)	122 (5)

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

References

Bruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cao, D.-K., Li, Y.-Z. & Zheng, L.-M. (2007). Inorg. Chem. 46, 7571–7578. Web of Science CSD CrossRef PubMed CAS Google Scholar
Cao, D.-K., Xie, X.-J., Li, Y.-Z. & Zheng, L.-M. (2008). Dalton Trans. pp. 5008–5015. Web of Science CSD CrossRef Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Web of Science CrossRef IUCr Journals Google Scholar
Mao, J.-G. (2007). Coord. Chem. Rev. 251, 1493–1520. Web of Science CrossRef CAS Google Scholar
Rao, C. N. R., Natarajan, S. & Vaidhyanathan, R. (2004). Angew. Chem. Int. Ed. 43, 1466–1468. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef IUCr Journals Google Scholar
Yang, T.-H., Liao, Y., Zheng, L.-M., Dinnebier, R. E., Su, Y.-H. & Ma, J. (2009). Chem. Commun. pp. 3023–3025. Web of Science CSD CrossRef Google Scholar

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Volume 65| Part 12| December 2009| Pages m1701-m1702

doi:10.1107/S160053680905065X

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

Di­aqua­bis­{[1-hydr­­oxy-2-(1H-imidazol-3-ium-1-yl)ethane-1,1-di­yl]bis­­(hydrogen phospho­nato)}manganese(II)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Diaquabis{[1-hydroxy-2-(1H-imidazol-3-ium-1-yl)ethane-1,1-diyl]bis(hydrogen phosphonato)}manganese(II)