catena-Poly[[[bis­(4-methyl­benzoato-κ2O,O′)zinc(II)]-μ-4,4′-bipyridine-κ2N:N′] tetra­hydrate]

Li, X.-Y.; Han, Y.-F.; Li, J.-K.

doi:10.1107/S1600536809005571

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page m354

doi:10.1107/S1600536809005571

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catena-Poly[[[bis(4-methylbenzoato-κ²O,O′)zinc(II)]-μ-4,4′-bipyridine-κ²N:N′] tetrahydrate]

Xiao-Yan Li,^a Yin-Feng Han ^a ^* and Ji-Kun Li ^b

^aDepartment of Chemistry, Taishan University, 271000 Taishan, Shandong, People's Republic of China, and ^bDepartment of Materials Science and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: hanyf1978@163.com

(Received 17 September 2008; accepted 17 February 2009; online 28 February 2009)

The asymmetric unit of the title compound, {[Zn(C₇H₇O₂)₂(C₁₀H₈N₂)]·4H₂O}_n, contains a highly distorted octahedral Zn^II metal center strongly coordinated by two N atoms of two 4,4′-bipyridine (4,4′-bipy) ligands and chelated by two 4-methylbenzoate anions. The crystallographic inversion center and glide plane present at the center of the C—C single bond of 4,4′-bipy, along with the cis coordination motif of the 4,4′-bipy, lead to one-dimensional zigzag chains. There are a large number of water molecules in the crystal structure, which also form one-dimensional chains through O—H⋯O hydrogen bonds.

Related literature

For inorganic–organic hybrid frameworks containing d-block transition metal ions and pyridyl ligands, see: Batten & Robson (1998 ); Horikoshi & Mochida (2006 ); Fujita et al. (1994 ); Luan et al. (2005 ); Tao et al. (2002 ).

Experimental

Crystal data

[Zn(C₇H₇O₂)₂(C₁₀H₈N₂)]·4H₂O
M_r = 563.89
Monoclinic, C 2/c
a = 12.024 (5) Å
b = 18.803 (8) Å
c = 12.283 (5) Å
β = 98.063 (6)°
V = 2750 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.94 mm⁻¹
T = 298 K
0.25 × 0.23 × 0.22 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.799, T_max = 0.820
9512 measured reflections
2439 independent reflections
2306 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 0.90
2439 reflections
169 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4B⋯O4ⁱ	0.85	1.93	2.761 (7)	167
O3—H3A⋯O2ⁱⁱ	0.85	1.93	2.777 (4)	179
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[x, -y, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; 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 global, I. DOI: 10.1107/S1600536809005571/ez2143sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005571/ez2143Isup2.hkl

checkCIF report

Comment top

Recently much attention has been paid to inorganic-organic hybrid frameworks that contain d-block transition metal ions and pyridyl ligands (Batten & Robson, 1998; Horikoshi & Mochida, 2006). These inorganic-organic hybrid frameworks form a wide range of interesting network topologies, such as chains, ladders or grids (Fujita et al., 1994; Luan et al. 2005). In these compounds, the combination of 4,4'-bipy and carboxylate ligands is largely directed toward obtaining interesting topologies (Tao et al., 2002). Here, we report the synthesis and crystal structure of the title complex, 1, which combines 4,4'-bipy and 4-methylbenzoate ligands.

Single-crystal X-ray diffraction studies reveal that the asymmetric unit contains the basic building block of 1, C₂₆H₂₂N₂O₄Cd.4(H₂O), as shown in Figure 1. The highly distorted octahedral Zn^II metal center is strongly coordinated to two N atoms of two 4,4'-bipy ligands [Zn—N, 2.064 (2) Å] and chelated to two 4-methylbenzoate anions [Zn1—O1, 2.159 (3) Å and Zn1—O2, 2.261 (3) Å]. The crystallographic inversion center and glide plane present at the center of the carbon-carbon single bond of the 4,4'-bipy ligand generate one-dimensional zig-zag coordination polymers. The zig-zag chains run approximately in parallel, as shown in Figure 2. The N1—Zn1—N1A [A: -x, y, 0.5 - z] angle of 105.4 (3)°, contributes to the chelate formation of the 4-methylbenzoate anions. The dihedral angles between the planes through 4,4'-bipy and 4-methylbenzoate are 84.68 (2)°. The Zn···Zn distances separated by the 4,4'-bipy are 11.20 (2) Å. The large number of included water molecules form one-dimensional chains through O—H···O hydrogen bonds.

Related literature top

For inorganic–organic hybrid frameworks containing d-block transition metal ions and pyridyl ligands, see: Batten & Robson (1998); Horikoshi & Mochida (2006); Fujita et al. (1994); Luan et al. (2005); Tao et al. (2002).

Experimental top

Zinc dichloride hexahydrate (2 mmol), 4-methylbenzoic acid (4 mmol) and 4,4'-bipy (2 mmol) were dissolved in a 3:1 ethanol-water solution (20 ml). Aqueous 0.1 M sodium hydroxide was added until the solution registered a pH of 7. The solution was set aside for the growth of crystals over several days. Anal. calc. for C₂₆H₃₀N₂O₈Zn: C 55.38, H 5.36, N 4.97%. Found: C 55.25, H 5.40, N 4.86%.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); 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. The structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme (A: -x, y, 0.5 - z).
	Fig. 2. The zig-zag chains of (I), with dashed lines indicating O—H···O hydrogen bonds.

catena-Poly[[[bis(4-methylbenzoato-κ²O,O')zinc(II)]-µ-4,4'-bipyridine-κ²N:N'] tetrahydrate] top

Crystal data top

[Zn(C₇H₇O₂)₂(C₁₀H₈N₂)]·4H₂O	F(000) = 1176
M_r = 563.89	D_x = 1.362 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 921 reflections
a = 12.024 (5) Å	θ = 2.7–28.1°
b = 18.803 (8) Å	µ = 0.94 mm⁻¹
c = 12.283 (5) Å	T = 298 K
β = 98.063 (6)°	Block, yellow
V = 2750 (2) Å³	0.25 × 0.23 × 0.22 mm
Z = 4

Data collection top

Bruker APEX area-detector diffractometer	2439 independent reflections
Radiation source: fine-focus sealed tube	2306 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −14→14
T_min = 0.799, T_max = 0.820	k = −22→22
9512 measured reflections	l = −14→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0704P)² + 5.1543P] where P = (F_o² + 2F_c²)/3
2439 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Zn(C₇H₇O₂)₂(C₁₀H₈N₂)]·4H₂O	V = 2750 (2) Å³
M_r = 563.89	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 12.024 (5) Å	µ = 0.94 mm⁻¹
b = 18.803 (8) Å	T = 298 K
c = 12.283 (5) Å	0.25 × 0.23 × 0.22 mm
β = 98.063 (6)°

Data collection top

Bruker APEX area-detector diffractometer	2439 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2306 reflections with I > 2σ(I)
T_min = 0.799, T_max = 0.820	R_int = 0.065
9512 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 0.90	Δρ_max = 0.41 e Å⁻³
2439 reflections	Δρ_min = −0.36 e Å⁻³
169 parameters

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	Occ. (<1)
Zn1	0.0000	0.07933 (2)	0.2500	0.04633 (19)
O1	0.1310 (2)	0.06512 (15)	0.3876 (2)	0.0757 (7)
O2	0.1328 (2)	−0.00574 (12)	0.2496 (2)	0.0744 (6)
N1	0.0873 (2)	0.14583 (12)	0.15842 (18)	0.0468 (5)
C1	0.1739 (3)	0.01398 (17)	0.3444 (3)	0.0587 (8)
C2	0.2720 (2)	−0.02359 (15)	0.4060 (3)	0.0529 (7)
C3	0.2954 (3)	−0.01735 (18)	0.5189 (3)	0.0658 (8)
H3	0.2522	0.0127	0.5560	0.079*
C4	0.3823 (3)	−0.0552 (2)	0.5773 (3)	0.0734 (10)
H4	0.3961	−0.0507	0.6534	0.088*
C5	0.4488 (3)	−0.09957 (19)	0.5252 (3)	0.0695 (9)
C6	0.5420 (4)	−0.1422 (3)	0.5892 (4)	0.1006 (15)
H6A	0.5905	−0.1603	0.5399	0.151*
H6B	0.5105	−0.1811	0.6252	0.151*
H6C	0.5844	−0.1123	0.6432	0.151*
C7	0.4265 (3)	−0.1047 (2)	0.4118 (4)	0.0744 (10)
H7	0.4717	−0.1335	0.3748	0.089*
C8	0.3386 (3)	−0.06778 (18)	0.3519 (3)	0.0636 (8)
H8	0.3244	−0.0727	0.2759	0.076*
C9	0.1610 (3)	0.19327 (18)	0.2051 (2)	0.0670 (9)
H9	0.1695	0.1984	0.2811	0.080*
C10	0.2254 (3)	0.23496 (18)	0.1467 (2)	0.0650 (9)
H10	0.2751	0.2678	0.1831	0.078*
C11	0.2161 (2)	0.22802 (13)	0.0331 (2)	0.0436 (6)
C12	0.1406 (3)	0.17860 (16)	−0.0138 (2)	0.0528 (7)
H12	0.1312	0.1717	−0.0896	0.063*
C13	0.0785 (3)	0.13905 (17)	0.0500 (2)	0.0542 (7)
H13	0.0280	0.1059	0.0155	0.065*
O3	0.0969 (2)	0.14890 (13)	0.70161 (19)	0.0729 (7)
H3A	0.1086	0.1050	0.7156	0.088*
H3B	0.1308	0.1602	0.6479	0.088*	0.50
H3C	0.0269	0.1566	0.6855	0.088*	0.50
O4	0.2054 (4)	0.1867 (2)	0.5310 (4)	0.1517 (19)
H4A	0.1876	0.1557	0.4813	0.182*
H4B	0.2322	0.2228	0.5021	0.182*	0.50
H4C	0.1485	0.1983	0.5610	0.182*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0510 (3)	0.0440 (3)	0.0457 (3)	0.000	0.01289 (19)	0.000
O1	0.0696 (15)	0.0948 (17)	0.0643 (12)	0.0361 (14)	0.0153 (9)	0.0181 (11)
O2	0.0714 (15)	0.0537 (12)	0.0922 (16)	0.0085 (9)	−0.0095 (13)	0.0086 (10)
N1	0.0511 (13)	0.0467 (12)	0.0435 (12)	−0.0026 (10)	0.0095 (10)	0.0015 (9)
C1	0.0548 (18)	0.0560 (17)	0.069 (2)	0.0016 (14)	0.0215 (15)	0.0166 (15)
C2	0.0486 (16)	0.0478 (15)	0.0642 (18)	0.0014 (12)	0.0150 (13)	0.0029 (13)
C3	0.075 (2)	0.0558 (17)	0.067 (2)	0.0092 (16)	0.0112 (16)	−0.0018 (15)
C4	0.082 (3)	0.0650 (19)	0.069 (2)	0.0048 (19)	−0.0048 (18)	0.0014 (17)
C5	0.0543 (19)	0.0577 (18)	0.093 (3)	0.0000 (15)	−0.0008 (18)	0.0053 (18)
C6	0.074 (3)	0.087 (3)	0.134 (4)	0.015 (2)	−0.008 (3)	0.015 (3)
C7	0.058 (2)	0.062 (2)	0.107 (3)	0.0102 (16)	0.0253 (19)	−0.005 (2)
C8	0.062 (2)	0.0624 (18)	0.069 (2)	0.0046 (15)	0.0179 (16)	−0.0025 (15)
C9	0.093 (3)	0.070 (2)	0.0378 (14)	−0.0261 (18)	0.0110 (15)	−0.0016 (14)
C10	0.086 (2)	0.0665 (19)	0.0415 (15)	−0.0329 (17)	0.0068 (14)	−0.0032 (13)
C11	0.0483 (14)	0.0419 (13)	0.0410 (13)	0.0010 (11)	0.0071 (11)	0.0014 (10)
C12	0.0562 (17)	0.0639 (17)	0.0387 (13)	−0.0126 (14)	0.0082 (12)	−0.0048 (12)
C13	0.0552 (17)	0.0625 (17)	0.0465 (15)	−0.0146 (14)	0.0122 (12)	−0.0072 (13)
O3	0.0812 (17)	0.0674 (14)	0.0682 (15)	0.0017 (12)	0.0035 (12)	0.0014 (11)
O4	0.194 (4)	0.105 (3)	0.183 (4)	−0.051 (3)	0.121 (4)	−0.034 (3)

Geometric parameters (Å, º) top

Zn1—N1ⁱ	2.064 (2)	C6—H6A	0.9600
Zn1—N1	2.064 (2)	C6—H6B	0.9600
Zn1—O1	2.159 (3)	C6—H6C	0.9600
Zn1—O1ⁱ	2.159 (3)	C7—C8	1.386 (5)
Zn1—O2	2.261 (3)	C7—H7	0.9300
Zn1—O2ⁱ	2.261 (3)	C8—H8	0.9300
Zn1—C1ⁱ	2.559 (3)	C9—C10	1.372 (4)
Zn1—C1	2.559 (3)	C9—H9	0.9300
O1—C1	1.245 (4)	C10—C11	1.390 (4)
O2—C1	1.255 (4)	C10—H10	0.9300
N1—C9	1.330 (4)	C11—C12	1.369 (4)
N1—C13	1.328 (4)	C11—C11ⁱⁱ	1.481 (5)
C1—C2	1.487 (4)	C12—C13	1.374 (4)
C2—C8	1.386 (4)	C12—H12	0.9300
C2—C3	1.381 (5)	C13—H13	0.9300
C3—C4	1.379 (5)	O3—H3A	0.8501
C3—H3	0.9300	O3—H3B	0.8500
C4—C5	1.374 (6)	O3—H3C	0.8500
C4—H4	0.9300	O4—H4A	0.8500
C5—C7	1.385 (6)	O4—H4B	0.8501
C5—C6	1.506 (5)	O4—H4C	0.8501

N1ⁱ—Zn1—N1	105.44 (13)	C4—C3—C2	120.7 (3)
N1ⁱ—Zn1—O1	91.10 (10)	C4—C3—H3	119.6
N1—Zn1—O1	97.52 (10)	C2—C3—H3	119.6
N1ⁱ—Zn1—O1ⁱ	97.52 (10)	C5—C4—C3	121.3 (4)
N1—Zn1—O1ⁱ	91.10 (9)	C5—C4—H4	119.4
O1—Zn1—O1ⁱ	165.78 (15)	C3—C4—H4	119.4
N1ⁱ—Zn1—O2	147.44 (10)	C4—C5—C7	117.8 (3)
N1—Zn1—O2	90.82 (10)	C4—C5—C6	121.3 (4)
O1—Zn1—O2	58.40 (10)	C7—C5—C6	120.8 (4)
O1ⁱ—Zn1—O2	110.41 (10)	C5—C6—H6A	109.5
N1ⁱ—Zn1—O2ⁱ	90.82 (10)	C5—C6—H6B	109.5
N1—Zn1—O2ⁱ	147.44 (10)	H6A—C6—H6B	109.5
O1—Zn1—O2ⁱ	110.41 (10)	C5—C6—H6C	109.5
O1ⁱ—Zn1—O2ⁱ	58.40 (10)	H6A—C6—H6C	109.5
O2—Zn1—O2ⁱ	89.92 (14)	H6B—C6—H6C	109.5
N1ⁱ—Zn1—C1ⁱ	95.29 (10)	C8—C7—C5	121.6 (3)
N1—Zn1—C1ⁱ	119.32 (10)	C8—C7—H7	119.2
O1—Zn1—C1ⁱ	139.05 (12)	C5—C7—H7	119.2
O1ⁱ—Zn1—C1ⁱ	29.05 (10)	C7—C8—C2	119.7 (3)
O2—Zn1—C1ⁱ	101.07 (10)	C7—C8—H8	120.2
O2ⁱ—Zn1—C1ⁱ	29.36 (10)	C2—C8—H8	120.2
N1ⁱ—Zn1—C1	119.31 (10)	N1—C9—C10	123.3 (3)
N1—Zn1—C1	95.29 (10)	N1—C9—H9	118.4
O1—Zn1—C1	29.05 (10)	C10—C9—H9	118.4
O1ⁱ—Zn1—C1	139.05 (12)	C9—C10—C11	120.0 (3)
O2—Zn1—C1	29.36 (10)	C9—C10—H10	120.0
O2ⁱ—Zn1—C1	101.07 (10)	C11—C10—H10	120.0
C1ⁱ—Zn1—C1	122.60 (15)	C12—C11—C10	116.2 (3)
C1—O1—Zn1	93.6 (2)	C12—C11—C11ⁱⁱ	122.0 (3)
C1—O2—Zn1	88.6 (2)	C10—C11—C11ⁱⁱ	121.8 (3)
C9—N1—C13	116.8 (2)	C13—C12—C11	120.6 (3)
C9—N1—Zn1	122.06 (19)	C13—C12—H12	119.7
C13—N1—Zn1	120.93 (19)	C11—C12—H12	119.7
O1—C1—O2	119.4 (3)	N1—C13—C12	123.2 (3)
O1—C1—C2	119.8 (3)	N1—C13—H13	118.4
O2—C1—C2	120.8 (3)	C12—C13—H13	118.4
O1—C1—Zn1	57.36 (18)	H3A—O3—H3B	108.4
O2—C1—Zn1	62.03 (18)	H3A—O3—H3C	110.1
C2—C1—Zn1	176.3 (2)	H3B—O3—H3C	110.1
C8—C2—C3	118.8 (3)	H4A—O4—H4B	108.7
C8—C2—C1	120.7 (3)	H4A—O4—H4C	110.5
C3—C2—C1	120.4 (3)	H4B—O4—H4C	110.5

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4B···O4ⁱⁱⁱ	0.85	1.93	2.761 (7)	167
O3—H3A···O2^iv	0.85	1.93	2.777 (4)	179

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

Experimental details

Crystal data
Chemical formula	[Zn(C₇H₇O₂)₂(C₁₀H₈N₂)]·4H₂O
M_r	563.89
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	12.024 (5), 18.803 (8), 12.283 (5)
β (°)	98.063 (6)
V (Å³)	2750 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.94
Crystal size (mm)	0.25 × 0.23 × 0.22

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.799, 0.820
No. of measured, independent and observed [I > 2σ(I)] reflections	9512, 2439, 2306
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 0.90
No. of reflections	2439
No. of parameters	169
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.36

Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), 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
O4—H4B···O4ⁱ	0.85	1.93	2.761 (7)	167.3
O3—H3A···O2ⁱⁱ	0.85	1.93	2.777 (4)	178.8

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

Acknowledgements

The authors thank the Postgraduate Foundation of Taishan University (grant No. Y06-2-12) for financial support.

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