catena-Poly[[[aqua­(formato-κO)(1,10-phenanthroline-κ2N,N′)manganese(II)]-μ-formato-κ2O:O′] monohydrate]

Xu, W.

doi:10.1107/S1600536811020575

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m893

doi:10.1107/S1600536811020575

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catena-Poly[[[aqua(formato-κO)(1,10-phenanthroline-κ²N,N′)manganese(II)]-μ-formato-κ²O:O′] monohydrate]

Wei Xu ^a ^*

^aCenter of Applied Solid State Chemistry Research, Ningbo University, Ningbo 315211, People's Republic of China
^*Correspondence e-mail: xuwei@nbu.edu.cn

(Received 17 May 2011; accepted 29 May 2011; online 11 June 2011)

The title compound, {[Mn(HCOO)₂(C₁₂H₈N₂)(H₂O)]·H₂O}_n, consists of polymeric chains of the complex [Mn(HCOO)₂(phen)(H₂O)]_∞ (phen is 1,10-phenanthroline) with solvent water molecules. The chains contain six-coordinate Mn^II ions bridged by formate anions. They are further extended into a three-dimensional network via O—H⋯O hydrogen-bonding interactions and interchain π–π stacking interactions, with a centroid–centroid distance of 3.679 (4) Å.

Related literature

For the design and synthesis of coordination polymer complexes and their potential applications, see: Robin & Fromm (2006 ); Farrusseng et al. (2008 ); Chen et al. (2010 ). For the formate anion as a ligand, see: Yuan et al. (2008 ); Hagen et al. (2009 ); Hu et al. (2009 ); Paredes-Gaecía (2009 ). For a related structure, see: Janiak (2000 ).

Experimental

Crystal data

[Mn(HCO₂)₂(C₁₂H₈N₂)(H₂O)]·H₂O
M_r = 361.21
Orthorhombic, P n a 2₁
a = 19.260 (4) Å
b = 12.161 (2) Å
c = 6.5493 (13) Å
V = 1534.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.89 mm⁻¹
T = 295 K
0.31 × 0.12 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.664, T_max = 0.791
11493 measured reflections
2644 independent reflections
1921 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.111
S = 1.20
2644 reflections
209 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.93 e Å⁻³
Absolute structure: Flack (1983 ), 1165 Friedel pairs
Flack parameter: 0.01 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯O2	0.83	1.96	2.713 (5)	150
O5—H5C⋯O6	0.85	1.76	2.601 (6)	177
O6—H6B⋯O4ⁱ	0.83	1.88	2.693 (8)	166
O6—H6C⋯O4ⁱⁱ	0.83	2.13	2.864 (9)	145
Symmetry codes: (i) $[-x+1, -y, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020575/fj2422sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020575/fj2422Isup2.hkl

checkCIF report

Comment top

In recent years, extensive efforts have been dedicated to the design and construction of coordination polymers because their supramolecular architectures with specific topologies may endow them with promising properties for material chemistry, such as gas sorption, storage and separations, molecular recognition, heterogeneous catalysis, nonlinear optics and magnetic properties (Robin & Fromm, 2006; Farrusseng, et al., 2008; Chen, et al., 2010). Investigations on a series of transition metal formate anions showed that it tend to function as a bidentate ligand to bridge metal atoms into one-dimensional chains, two-dimensional layers and three-dimensional networks (Hagen, et al., 2009; Hu, et al., 2009; Paredes-Gaecía, 2009). In the present contribution, we report a new manganese(II) complex, [Mn(HCOO)₂(phen)(H₂O)].H₂O (I), resulting from self-assembly of Mn²⁺ ions, 1,10-phenanthroline and formic acid. It is isostructural with the previously reported [Co(HCOO)₂(phen)(H₂O)].H₂O complex (Yuan, et al., 2008).

Compound I consists of an neutral one-dimensional zigzag chains [Mn(HCOO)₂(phen)(H₂O)]_n and lattice water molecules. As shown in Fig. 1, each Mn atom is octahedral coordination by two N atoms of phen ligand, two O atoms of two bridging formate anions, one O atom of one terminal formate anion and one O atom of the coordination water molecule. The octehedral coordination around the Mn atoms are strongly distorted since the diametrical and non-diametrical bond angles indicate significant deviations from 180° and 90°, respectively. The Mn-O distances are in the range of 2.134 (5)-2.228 (4) Å, while the Mn-N distances are 2.246 (5) and 2.295 (5) Å. Then two neighboring Mn^II centers connected by formate anion with the distance of 5.474 (5) Å form one-dimensional zigzag chain along [001] (Fig. 2).

The coordinated water molecule forms a strong intra-chain hydrogen bond to the carboxyl O2 with d(O···O) = 2.713 (5) Å and <O-H···O = 150°. There are three kinds of independent inter-chain hydrogen bonds responsible for the two-dimensional layers assembly (Fig. 3, Table 1). One kind of the inter-chain O-H···O hydrogen bonds is formed between the O-H group of coordinated water molecules acting as acceptors (the O···O distance is 2.601 (6) Å with a O-H···O angle of 177°). The other two kinds are formed between the O-H groups of uncoordinated water molecules and the uncoordinated oxygen atoms of the carboxyl groups from the coordianted terminal formate anions in two adjacent chains, with the different O···O distances of 2.693 (8) and 2.864 (9) Å, and two different O-H···O angles of 166° and 145°, respectively. The phen ligands chelating Mn atoms exhibit nearly perfect coplanarity. Two neighboring phen ligands of different chains parallelly face opposite directions at an interplanar centroid to centroid distance of 3.679 (4) Å, with the quinoline fragments partially covered, which suggests significant inter-chain π-π stacking interactions (Janiak, 2000). Acoording to the above description, it is clear that the π-π interactions and inter-chain hydrogen bonding interactions are responsible for the supramolecular assembly of the three-dimensional network.

Related literature top

For the design and synthesis of coordination polymer complexes and their potential applications, see: Robin & Fromm (2006); Farrusseng et al. (2008); Chen et al. (2010). For the formate anion as a ligand, see: Yuan et al. (2008); Hagen et al. (2009); Hu et al. (2009); Paredes-Gaecía (2009). For a related structure, see: Janiak (2000).

Experimental top

Addition of 2.0 mL (1.0 M) NaOH to a stirred aqueous of 0.201 g (1.0 mmol) MnCl₂.4H₂O in 5.0 mL H₂O yield yellowish precipitate, which was then separated by centrifugation, followed by washing with double-distilled water until no detectable Cl^- anions in supernatant. The precipitate was added to a stirred ethanolic aqueous solution of 0.198 g (1.0 mmol) 1,10-phenanthroline monohydrate in 20 mL EtOH/H₂O (v:v = 1: 1). To the mixture was added 2.0 mL (1.0 M) HCOOH and the yellowish suspension was further stirred for ca. 30 min. After filtration, the solution (pH = 6.58) was allowed to stand at room temperature. Slow evaporation for two weeks affored yellowish crystals (yield 62% based on the initial MnCl₂.4H₂O input).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP view of the title compound (40% thermal ellipsoids) showing the atom-labeling scheme. [Symmetry Code: (i) 1-x, 1-y, 1/2+z)
	Fig. 2. one dimensional zigzag chain along [001]
	Fig. 3. A view of a single layer of I, hydrogen-bonding is indicated as dashed lines.

catena-Poly[[[aqua(formato-κO)(1,10-phenanthroline- κ²N,N')manganese(II)]-µ-formato-κ²O:O'] monohydrate] top

Crystal data top

[Mn(HCO₂)₂(C₁₂H₈N₂)(H₂O)]·H₂O	F(000) = 740
M_r = 361.21	D_x = 1.564 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8376 reflections
a = 19.260 (4) Å	θ = 3.4–27.4°
b = 12.161 (2) Å	µ = 0.89 mm⁻¹
c = 6.5493 (13) Å	T = 295 K
V = 1534.0 (5) Å³	Needle, yellow
Z = 4	0.31 × 0.12 × 0.09 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2644 independent reflections
Radiation source: fine-focus sealed tube	1921 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 25.0°, θ_min = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −22→22
T_min = 0.664, T_max = 0.791	k = −14→14
11493 measured reflections	l = −7→7

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0135P)² + 2.7605P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.111	(Δ/σ)_max < 0.001
S = 1.20	Δρ_max = 0.70 e Å⁻³
2644 reflections	Δρ_min = −0.93 e Å⁻³
209 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0025 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1165 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.01 (4)

Crystal data top

[Mn(HCO₂)₂(C₁₂H₈N₂)(H₂O)]·H₂O	V = 1534.0 (5) Å³
M_r = 361.21	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 19.260 (4) Å	µ = 0.89 mm⁻¹
b = 12.161 (2) Å	T = 295 K
c = 6.5493 (13) Å	0.31 × 0.12 × 0.09 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2644 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1921 reflections with I > 2σ(I)
T_min = 0.664, T_max = 0.791	R_int = 0.047
11493 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.111	Δρ_max = 0.70 e Å⁻³
S = 1.20	Δρ_min = −0.93 e Å⁻³
2644 reflections	Absolute structure: Flack (1983), 1165 Friedel pairs
209 parameters	Absolute structure parameter: 0.01 (4)
1 restraint

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 > 2σ(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
Mn1	0.57992 (4)	0.37155 (6)	0.67916 (16)	0.0454 (3)
N1	0.6768 (3)	0.3026 (4)	0.5202 (9)	0.0525 (13)
N2	0.6704 (2)	0.4167 (4)	0.8785 (8)	0.0470 (12)
C1	0.6796 (4)	0.2444 (5)	0.3480 (10)	0.068 (2)
H1A	0.6385	0.2277	0.2802	0.082*
C2	0.7429 (5)	0.2076 (6)	0.2658 (13)	0.087 (3)
H2A	0.7435	0.1662	0.1464	0.105*
C3	0.8034 (5)	0.2333 (7)	0.3629 (15)	0.091 (3)
H3A	0.8455	0.2099	0.3084	0.110*
C4	0.8027 (4)	0.2946 (6)	0.5440 (13)	0.073 (2)
C5	0.8643 (4)	0.3266 (7)	0.6559 (18)	0.093 (3)
H5A	0.9077	0.3074	0.6049	0.112*
C6	0.8603 (4)	0.3828 (8)	0.8299 (16)	0.096 (3)
H6A	0.9010	0.4006	0.8988	0.116*
C7	0.7958 (3)	0.4161 (6)	0.9127 (12)	0.067 (2)
C8	0.7882 (4)	0.4722 (7)	1.0989 (12)	0.079 (3)
H8A	0.8274	0.4906	1.1742	0.095*
C9	0.7246 (4)	0.4999 (5)	1.1701 (14)	0.0725 (19)
H9A	0.7197	0.5372	1.2932	0.087*
C10	0.6668 (4)	0.4714 (5)	1.0556 (11)	0.0600 (17)
H10A	0.6233	0.4913	1.1043	0.072*
C11	0.7335 (3)	0.3880 (5)	0.8082 (10)	0.0513 (16)
C12	0.7379 (3)	0.3280 (5)	0.6200 (10)	0.0553 (19)
C13	0.5493 (3)	0.5910 (5)	0.4494 (9)	0.0508 (15)
H13	0.5562	0.6662	0.4325	0.061*
O1	0.5939 (2)	0.5392 (3)	0.5480 (7)	0.0537 (11)
O2	0.4966 (2)	0.5501 (3)	0.3718 (7)	0.0599 (12)
C14	0.5604 (4)	0.1288 (6)	0.7827 (12)	0.071 (2)
H14	0.5642	0.1173	0.6428	0.086*
O3	0.5629 (3)	0.2210 (4)	0.8388 (7)	0.0747 (14)
O4	0.5534 (4)	0.0457 (4)	0.8904 (10)	0.112 (2)
O5	0.5090 (2)	0.3307 (3)	0.4372 (7)	0.0719 (14)
H5B	0.4990	0.3890	0.3784	0.108*
H5C	0.5014	0.2710	0.3749	0.108*
O6	0.4906 (3)	0.1479 (4)	0.2384 (9)	0.115 (2)
H6B	0.4780	0.0927	0.3042	0.173*
H6C	0.5237	0.1210	0.1706	0.173*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0384 (4)	0.0469 (4)	0.0509 (5)	0.0040 (4)	0.0029 (6)	−0.0014 (6)
N1	0.052 (3)	0.052 (3)	0.054 (3)	0.013 (2)	0.016 (3)	0.008 (3)
N2	0.039 (3)	0.053 (3)	0.049 (3)	0.005 (2)	0.002 (2)	0.004 (3)
C1	0.094 (6)	0.053 (4)	0.056 (4)	0.020 (4)	0.035 (4)	−0.002 (4)
C2	0.129 (8)	0.061 (4)	0.073 (5)	0.023 (5)	0.050 (6)	0.012 (4)
C3	0.096 (7)	0.075 (6)	0.103 (7)	0.043 (5)	0.049 (6)	0.036 (6)
C4	0.062 (5)	0.080 (5)	0.078 (5)	0.021 (4)	0.030 (4)	0.041 (4)
C5	0.039 (4)	0.129 (7)	0.112 (8)	0.019 (4)	0.019 (5)	0.063 (8)
C6	0.050 (5)	0.133 (9)	0.106 (8)	−0.001 (5)	−0.002 (5)	0.059 (7)
C7	0.043 (4)	0.078 (5)	0.078 (6)	−0.007 (4)	−0.011 (4)	0.040 (4)
C8	0.075 (5)	0.083 (5)	0.081 (6)	−0.026 (4)	−0.036 (4)	0.033 (4)
C9	0.082 (5)	0.069 (4)	0.066 (4)	−0.018 (4)	−0.029 (5)	0.013 (5)
C10	0.069 (5)	0.058 (4)	0.053 (4)	−0.001 (4)	−0.005 (4)	0.005 (3)
C11	0.045 (4)	0.057 (4)	0.051 (4)	0.005 (3)	0.003 (3)	0.023 (3)
C12	0.040 (4)	0.057 (4)	0.068 (5)	0.017 (3)	0.011 (3)	0.024 (3)
C13	0.047 (4)	0.047 (4)	0.058 (4)	0.000 (3)	−0.007 (3)	0.013 (3)
O1	0.047 (2)	0.049 (2)	0.065 (3)	−0.0018 (19)	−0.016 (2)	0.008 (2)
O2	0.050 (3)	0.052 (3)	0.078 (3)	0.004 (2)	−0.019 (2)	0.008 (2)
C14	0.090 (6)	0.048 (4)	0.076 (5)	0.019 (4)	0.024 (4)	0.015 (4)
O3	0.090 (4)	0.058 (3)	0.075 (4)	0.005 (3)	0.021 (3)	0.002 (3)
O4	0.164 (6)	0.056 (3)	0.117 (5)	0.008 (4)	0.023 (5)	0.024 (4)
O5	0.085 (4)	0.048 (3)	0.082 (3)	0.000 (2)	−0.032 (3)	0.001 (2)
O6	0.165 (6)	0.085 (4)	0.095 (5)	−0.030 (4)	0.028 (4)	−0.033 (3)

Geometric parameters (Å, º) top

Mn1—O3	2.134 (5)	C6—H6A	0.9300
Mn1—O5	2.150 (4)	C7—C8	1.405 (11)
Mn1—O2ⁱ	2.161 (4)	C7—C11	1.422 (9)
Mn1—O1	2.228 (4)	C8—C9	1.353 (10)
Mn1—N2	2.246 (5)	C8—H8A	0.9300
Mn1—N1	2.295 (5)	C9—C10	1.385 (9)
N1—C1	1.333 (8)	C9—H9A	0.9300
N1—C12	1.382 (8)	C10—H10A	0.9300
N2—C10	1.339 (9)	C11—C12	1.435 (9)
N2—C11	1.346 (7)	C13—O2	1.240 (7)
C1—C2	1.406 (10)	C13—O1	1.245 (7)
C1—H1A	0.9300	C13—H13	0.9300
C2—C3	1.364 (11)	O2—Mn1ⁱⁱ	2.161 (4)
C2—H2A	0.9300	C14—O3	1.180 (8)
C3—C4	1.401 (12)	C14—O4	1.240 (8)
C3—H3A	0.9300	C14—H14	0.9300
C4—C12	1.403 (9)	O5—H5B	0.8290
C4—C5	1.448 (12)	O5—H5C	0.8460
C5—C6	1.331 (13)	O6—H6B	0.8339
C5—H5A	0.9300	O6—H6C	0.8420
C6—C7	1.414 (11)

O3—Mn1—O5	93.75 (19)	C4—C5—H5A	119.2
O3—Mn1—O2ⁱ	89.28 (17)	C5—C6—C7	121.8 (9)
O5—Mn1—O2ⁱ	95.71 (18)	C5—C6—H6A	119.1
O3—Mn1—O1	172.92 (19)	C7—C6—H6A	119.1
O5—Mn1—O1	90.21 (16)	C8—C7—C6	124.3 (8)
O2ⁱ—Mn1—O1	84.49 (17)	C8—C7—C11	116.5 (7)
O3—Mn1—N2	92.55 (19)	C6—C7—C11	119.1 (8)
O5—Mn1—N2	167.9 (2)	C9—C8—C7	121.0 (7)
O2ⁱ—Mn1—N2	94.70 (18)	C9—C8—H8A	119.5
O1—Mn1—N2	84.64 (16)	C7—C8—H8A	119.5
O3—Mn1—N1	91.92 (18)	C8—C9—C10	118.6 (8)
O5—Mn1—N1	95.6 (2)	C8—C9—H9A	120.7
O2ⁱ—Mn1—N1	168.5 (2)	C10—C9—H9A	120.7
O1—Mn1—N1	93.53 (17)	N2—C10—C9	123.5 (7)
N2—Mn1—N1	73.86 (18)	N2—C10—H10A	118.3
C1—N1—C12	119.0 (6)	C9—C10—H10A	118.3
C1—N1—Mn1	127.6 (5)	N2—C11—C7	122.3 (7)
C12—N1—Mn1	113.4 (4)	N2—C11—C12	118.6 (6)
C10—N2—C11	118.2 (6)	C7—C11—C12	119.0 (6)
C10—N2—Mn1	125.8 (4)	N1—C12—C4	121.7 (7)
C11—N2—Mn1	116.0 (4)	N1—C12—C11	118.0 (6)
N1—C1—C2	121.9 (8)	C4—C12—C11	120.3 (7)
N1—C1—H1A	119.1	O2—C13—O1	125.0 (6)
C2—C1—H1A	119.1	O2—C13—H13	117.5
C3—C2—C1	119.3 (8)	O1—C13—H13	117.5
C3—C2—H2A	120.3	C13—O1—Mn1	125.5 (4)
C1—C2—H2A	120.3	C13—O2—Mn1ⁱⁱ	128.4 (4)
C2—C3—C4	120.5 (8)	O3—C14—O4	127.0 (8)
C2—C3—H3A	119.7	O3—C14—H14	116.5
C4—C3—H3A	119.7	O4—C14—H14	116.5
C3—C4—C12	117.6 (8)	C14—O3—Mn1	131.9 (5)
C3—C4—C5	124.3 (8)	Mn1—O5—H5B	107.1
C12—C4—C5	118.1 (8)	Mn1—O5—H5C	131.6
C6—C5—C4	121.6 (8)	H5B—O5—H5C	118.0
C6—C5—H5A	119.2	H6B—O6—H6C	100.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O2	0.83	1.96	2.713 (5)	150
O5—H5C···O6	0.85	1.76	2.601 (6)	177
O6—H6B···O4ⁱⁱⁱ	0.83	1.88	2.693 (8)	166
O6—H6C···O4^iv	0.83	2.13	2.864 (9)	145

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

Experimental details

Crystal data
Chemical formula	[Mn(HCO₂)₂(C₁₂H₈N₂)(H₂O)]·H₂O
M_r	361.21
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	19.260 (4), 12.161 (2), 6.5493 (13)
V (Å³)	1534.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.31 × 0.12 × 0.09

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.664, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	11493, 2644, 1921
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.111, 1.20
No. of reflections	2644
No. of parameters	209
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.93
Absolute structure	Flack (1983), 1165 Friedel pairs
Absolute structure parameter	0.01 (4)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), 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
O5—H5B···O2	0.83	1.96	2.713 (5)	150
O5—H5C···O6	0.85	1.76	2.601 (6)	177
O6—H6B···O4ⁱ	0.83	1.88	2.693 (8)	166
O6—H6C···O4ⁱⁱ	0.83	2.13	2.864 (9)	145

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

Acknowledgements

This project was supported by the Scientific Research Fund of the Zhejiang Provincial Education Department (grant No. Y201017782) and the Scientific Research Fund of Ningbo University (grant No. XKL09078). Thanks are also extended to the K. C. Wong Magna Fund of Ningbo University.

References

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