catena-Poly[[dichloridozinc(II)]-μ-2,5-di-4-pyridyl-1,3,4-thia­diazole-κ2N2:N5]

Chen, L.-J.; Yang, M.-X.; Chen, X.-H.; Lin, S.

doi:10.1107/S1600536808001967

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m393

doi:10.1107/S1600536808001967

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catena-Poly[[dichloridozinc(II)]-μ-2,5-di-4-pyridyl-1,3,4-thiadiazole-κ²N²:N⁵]

Li-Juan Chen,^a ^* Ming-Xing Yang,^a Xiao-Hua Chen ^a and Shen Lin ^a

^aCollege of Chemistry and Materials Science, Fuzhou, Fujian 350007, People's Republic of China
^*Correspondence e-mail: ljchen@ms.fjirsm.ac.cn

(Received 17 December 2007; accepted 18 January 2008; online 23 January 2008)

The title compound, [ZnCl₂(C₁₂H₈N₄S)]_n, was obtained by crystallization of 2,5-di-4-pyridyl-1,3,4-thiadiazole with ZnCl₂ in an MeOH/CHCl₃ solvent system. The structure contains infinite chains of ZnCl₂ units connected by the bifunctional thiadiazole ligands, with Zn^II adopting a distorted tetrahedral coordination geometry. The dihedral angle between the two pyridyl rings in each ligand is 34.3 (1)°, and the dihedral angles between the thiadiazole ring and the two pyridyl rings are 18.3 (2) and 16.1 (2)°. The shortest Zn⋯Zn distance within each polymeric chain is 11.862 (3) Å, while the shortest interchain Zn⋯Zn distance is 7.057 (3) Å.

Related literature

For related literature, see: Chen et al. (2007 ); Dong, Ma & Huang (2003 ); Dong, Ma, Huang, Guo & Smith (2003 ); Du et al. (2003 ); Fujita (1998 ); Huang et al. (2004 ); Inoue et al. (1996 ); Maekawam et al. (2000 ); Moulton & Zaworotko (2001 ); Xiong et al. (2001 ).

Experimental

Crystal data

[ZnCl₂(C₁₂H₈N₄S)]
M_r = 376.55
Monoclinic, P 2₁ /n
a = 12.9990 (13) Å
b = 5.4039 (5) Å
c = 20.195 (2) Å
β = 101.459 (4)°
V = 1390.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.29 mm⁻¹
T = 293 (2) K
0.20 × 0.12 × 0.04 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002 ) T_min = 0.690, T_max = 0.912
10073 measured reflections
3155 independent reflections
2688 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.089
S = 1.03
3155 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Zn1—N4ⁱ	2.060 (2)
Zn1—N1	2.060 (2)
Zn1—Cl1	2.1939 (8)
Zn1—Cl2	2.2402 (8)

N4ⁱ—Zn1—N1	103.11 (9)
N4ⁱ—Zn1—Cl1	107.44 (6)
N1—Zn1—Cl1	107.78 (7)
N4ⁱ—Zn1—Cl2	104.00 (7)
N1—Zn1—Cl2	104.64 (6)
Cl1—Zn1—Cl2	127.44 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001967/bi2274sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001967/bi2274Isup2.hkl

checkCIF report

Comment top

Much current research activity of supramolecular coordination polymers with novel topologies and structural motifs is driven by their encouraging potential applications in the fields of nonlinear optics, catalysis and separation, magnetism and molecular recognition (Moulton & Zaworotko, 2001, Xiong et al., 2001, Inoue et al., 1996). Therefore, the discovery and rational design of such coordination polymers is an important and very active topic. One useful strategy for the discovery of novel coordination polymers has been the use of various spacer ligands as the building block (Du et al., 2003, Chen et al., 2007). So far, a wide range of infinite frameworks have already been generated with simple 4,4'-bipyridyl-based ligands (Maekawam et al., 2000, Fujita, 1998).

As previously reported (Dong, Ma & Huang, 2003, Huang et al., 2004), oxadiazole-containing ligands can take versatile bonding modes (it can act as mono-, bi-, tri- and even tetradentate ligand) and the structural geometries of the ligands themselves are also variable. On the other hand, d¹⁰ transition metal-containing complexes often show interesting optical properties. Our interest in the supramolecular coordination polymers lead us to use 2,5-di-4-pyridyl-1,3,4-thiadiazole (L) and ZnCl₂ as precursors to generate the title compound.

Crystallization of L and ZnCl₂ in MeOH/CHCl₃ mixed solvent system at room temperature yield the title compound, [Zn(C₁₂H₈N₄S)Cl₂]_n. The crystal structure is composed of 1-D zigzag chains with ZnCl₂ units connected to each other by the N-donor bifunctional ligands. As shown in Fig. 1, the Zn^II center adopts a distorted tetrahedral coordination geometry, defined by two N donors from two 2,5-di-4-pyridyl-1,3,4- thiadiazole ligands (L) and terminal chloride ligands. Both Zn—N bond distances are 2.060 (2) Å, and the two Zn—Cl bond distances are 2.1938 (8) and 2.2402 (8) Å, respectively. The greatest angular distortion from tetrahedral geometry is exhibited by the Cl—Zn—Cl angle of 127.44 (3) ° and by the N—Zn—N angle of 103.11 (9) °. All these values compare well to those reported in other [Zn(4,4'-bipy)] compounds (Dong, Ma, Huang, Guo et al., 2003). The two pyridyl ring groups in each ligand are not coplanar, and the dihedral angle between them is 34.3 (1) °. The dihedral angles between the thiadiazole ring and the two pyridyl ring groups in each ligand are 18.3 (2) ° and 16.1 (2) °. The intrachain Zn···Zn distance is 11.862 (3) Å, while the shortest interchain Zn···Zn distance is 7.057 (3) Å.

In the crystal, the 1-D zigzag chains stack along crystallographic β axis. In the ac plane (Fig. 2), neighboring chains are arranged in opposite directions, and are stacked either in a shoulder-to-shoulder or a staggered fashion.

Related literature top

For related literature, see: Chen et al. (2007); Dong, Ma & Huang (2003); Dong, Ma, Huang, Guo et al. (2003); Du et al. (2003); Fujita (1998); Huang et al. (2004); Inoue et al. (1996); Maekawam et al. (2000); Moulton & Zaworotko (2001); Xiong et al. (2001).

Experimental top

A solution of ZnCl₂ (22.7 mg, 0.05 mmol) in MeOH (5 ml) was carefully layered on a solution of 2,5-di-4-pyridyl-1,3,4-thiadiazole (12 mg, 0.05 mmol) in CHCl₃ (5 ml) in a straight glass tube. After one week, colorless single crystals were obtained (yield ca 25% based on Zn).

Computing details top

Data collection: CrystalClear (Rigaku, 2002); cell refinement: CrystalClear (Rigaku, 2002); data reduction: CrystalClear (Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound showing 30% probability displacement ellipsoids (H atoms are omitted).

catena-Poly[[dichloridozinc(II)]-µ-2,5-di-4-pyridyl-1,3,4-thiadiazole- κ²N²:N⁵] top

Crystal data top

[ZnCl₂(C₁₂H₈N₄S)]	F(000) = 752
M_r = 376.55	D_x = 1.799 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2905 reflections
a = 12.9990 (13) Å	θ = 3.9–27.5°
b = 5.4039 (5) Å	µ = 2.29 mm⁻¹
c = 20.195 (2) Å	T = 293 K
β = 101.459 (4)°	Prism, white
V = 1390.3 (2) Å³	0.20 × 0.12 × 0.04 mm
Z = 4

Data collection top

Rigaku Mercury CCD diffractometer	3155 independent reflections
Radiation source: fine-focus sealed tube	2688 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω scans	θ_max = 27.5°, θ_min = 3.9°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)	h = −14→16
T_min = 0.690, T_max = 0.912	k = −7→6
10073 measured reflections	l = −26→26

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0439P)² + 0.6049P] where P = (F_o² + 2F_c²)/3
3155 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[ZnCl₂(C₁₂H₈N₄S)]	V = 1390.3 (2) Å³
M_r = 376.55	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.9990 (13) Å	µ = 2.29 mm⁻¹
b = 5.4039 (5) Å	T = 293 K
c = 20.195 (2) Å	0.20 × 0.12 × 0.04 mm
β = 101.459 (4)°

Data collection top

Rigaku Mercury CCD diffractometer	3155 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2002)	2688 reflections with I > 2σ(I)
T_min = 0.690, T_max = 0.912	R_int = 0.032
10073 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.04	Δρ_max = 0.43 e Å⁻³
3155 reflections	Δρ_min = −0.38 e Å⁻³
181 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
Zn1	1.45602 (2)	1.18961 (6)	0.680619 (15)	0.03305 (12)
S1	1.23784 (6)	0.24683 (15)	0.42060 (4)	0.04195 (19)
Cl1	1.34567 (6)	1.43843 (14)	0.71674 (4)	0.04576 (19)
Cl2	1.59540 (6)	1.29522 (15)	0.63700 (4)	0.0476 (2)
N1	1.37010 (17)	0.9563 (4)	0.60991 (10)	0.0325 (5)
N2	1.10437 (18)	0.3373 (5)	0.49394 (11)	0.0374 (5)
N3	1.06015 (18)	0.1586 (5)	0.45020 (12)	0.0385 (6)
N4	1.01683 (17)	−0.4543 (4)	0.25889 (10)	0.0320 (5)
C1	1.2665 (2)	0.9276 (5)	0.60620 (14)	0.0376 (6)
H1A	1.2329	1.0288	0.6325	0.045*
C2	1.2081 (2)	0.7546 (6)	0.56503 (14)	0.0370 (6)
H2A	1.1362	0.7423	0.5630	0.044*
C3	1.2576 (2)	0.5981 (5)	0.52646 (12)	0.0321 (6)
C4	1.3644 (2)	0.6283 (6)	0.53025 (14)	0.0397 (7)
H4A	1.4002	0.5273	0.5052	0.048*
C5	1.4169 (2)	0.8089 (6)	0.57142 (14)	0.0403 (7)
H5A	1.4883	0.8300	0.5727	0.048*
C6	1.1964 (2)	0.4066 (5)	0.48470 (12)	0.0308 (6)
C7	1.1201 (2)	0.0891 (5)	0.40919 (13)	0.0314 (6)
C8	1.0874 (2)	−0.1003 (5)	0.35760 (13)	0.0317 (6)
C9	1.0054 (2)	−0.2613 (5)	0.36310 (14)	0.0360 (6)
H9A	0.9736	−0.2536	0.4004	0.043*
C10	0.9723 (2)	−0.4310 (5)	0.31285 (13)	0.0364 (6)
H10A	0.9165	−0.5344	0.3165	0.044*
C11	1.0960 (2)	−0.3019 (5)	0.25406 (14)	0.0390 (7)
H11A	1.1278	−0.3178	0.2169	0.047*
C12	1.1329 (2)	−0.1232 (6)	0.30118 (14)	0.0389 (6)
H12A	1.1875	−0.0193	0.2954	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.03407 (19)	0.0322 (2)	0.03165 (17)	−0.00116 (13)	0.00357 (13)	0.00049 (13)
S1	0.0336 (4)	0.0522 (5)	0.0429 (4)	−0.0112 (3)	0.0145 (3)	−0.0163 (3)
Cl1	0.0474 (4)	0.0385 (4)	0.0521 (4)	0.0064 (3)	0.0115 (3)	−0.0035 (3)
Cl2	0.0436 (4)	0.0520 (5)	0.0500 (4)	−0.0069 (3)	0.0159 (3)	0.0043 (4)
N1	0.0314 (11)	0.0336 (13)	0.0313 (11)	0.0002 (9)	0.0032 (9)	−0.0022 (10)
N2	0.0351 (12)	0.0412 (14)	0.0370 (12)	−0.0051 (10)	0.0094 (10)	−0.0086 (11)
N3	0.0344 (12)	0.0436 (14)	0.0377 (12)	−0.0044 (11)	0.0075 (10)	−0.0077 (11)
N4	0.0343 (12)	0.0300 (12)	0.0309 (10)	0.0007 (9)	0.0045 (9)	0.0001 (9)
C1	0.0335 (14)	0.0388 (16)	0.0396 (14)	0.0016 (12)	0.0054 (12)	−0.0069 (13)
C2	0.0287 (14)	0.0399 (16)	0.0415 (15)	0.0031 (12)	0.0048 (12)	−0.0050 (13)
C3	0.0323 (13)	0.0339 (15)	0.0287 (12)	−0.0026 (11)	0.0024 (10)	0.0031 (11)
C4	0.0347 (15)	0.0472 (17)	0.0382 (14)	−0.0017 (13)	0.0096 (12)	−0.0131 (13)
C5	0.0291 (14)	0.0494 (19)	0.0424 (15)	−0.0044 (12)	0.0069 (12)	−0.0086 (14)
C6	0.0298 (13)	0.0323 (14)	0.0302 (12)	0.0016 (11)	0.0056 (10)	−0.0008 (11)
C7	0.0306 (13)	0.0315 (14)	0.0318 (12)	−0.0011 (11)	0.0054 (11)	0.0022 (11)
C8	0.0300 (13)	0.0326 (14)	0.0307 (12)	0.0009 (11)	0.0012 (10)	−0.0016 (11)
C9	0.0380 (15)	0.0404 (16)	0.0315 (13)	−0.0054 (12)	0.0119 (12)	−0.0001 (12)
C10	0.0379 (15)	0.0356 (16)	0.0365 (14)	−0.0072 (12)	0.0097 (12)	0.0005 (12)
C11	0.0371 (15)	0.0463 (18)	0.0361 (14)	−0.0061 (13)	0.0134 (12)	−0.0080 (13)
C12	0.0322 (14)	0.0443 (16)	0.0416 (15)	−0.0082 (13)	0.0106 (12)	−0.0040 (13)

Geometric parameters (Å, º) top

Zn1—N4ⁱ	2.060 (2)	C2—H2A	0.930
Zn1—N1	2.060 (2)	C3—C4	1.384 (4)
Zn1—Cl1	2.1939 (8)	C3—C6	1.466 (4)
Zn1—Cl2	2.2402 (8)	C4—C5	1.373 (4)
S1—C7	1.727 (3)	C4—H4A	0.930
S1—C6	1.729 (3)	C5—H5A	0.930
N1—C5	1.341 (3)	C7—C8	1.462 (4)
N1—C1	1.343 (3)	C8—C12	1.390 (4)
N2—C6	1.302 (3)	C8—C9	1.397 (4)
N2—N3	1.357 (3)	C9—C10	1.372 (4)
N3—C7	1.301 (3)	C9—H9A	0.930
N4—C10	1.337 (3)	C10—H10A	0.930
N4—C11	1.337 (3)	C11—C12	1.374 (4)
C1—C2	1.375 (4)	C11—H11A	0.930
C1—H1A	0.930	C12—H12A	0.930
C2—C3	1.391 (4)

N4ⁱ—Zn1—N1	103.11 (9)	C3—C4—H4A	120.3
N4ⁱ—Zn1—Cl1	107.44 (6)	N1—C5—C4	123.0 (3)
N1—Zn1—Cl1	107.78 (7)	N1—C5—H5A	118.5
N4ⁱ—Zn1—Cl2	104.00 (7)	C4—C5—H5A	118.5
N1—Zn1—Cl2	104.64 (6)	N2—C6—C3	122.0 (2)
Cl1—Zn1—Cl2	127.44 (3)	N2—C6—S1	113.3 (2)
C7—S1—C6	86.95 (13)	C3—C6—S1	124.68 (19)
C5—N1—C1	117.7 (2)	N3—C7—C8	122.0 (2)
C5—N1—Zn1	121.31 (18)	N3—C7—S1	113.6 (2)
C1—N1—Zn1	120.60 (18)	C8—C7—S1	124.45 (19)
C6—N2—N3	113.2 (2)	C12—C8—C9	117.7 (3)
C7—N3—N2	113.0 (2)	C12—C8—C7	122.4 (2)
C10—N4—C11	117.7 (2)	C9—C8—C7	119.9 (2)
C10—N4—Zn1ⁱⁱ	121.41 (18)	C10—C9—C8	119.3 (2)
C11—N4—Zn1ⁱⁱ	120.52 (18)	C10—C9—H9A	120.3
N1—C1—C2	122.6 (3)	C8—C9—H9A	120.3
N1—C1—H1A	118.7	N4—C10—C9	122.9 (3)
C2—C1—H1A	118.7	N4—C10—H10A	118.6
C1—C2—C3	119.4 (3)	C9—C10—H10A	118.6
C1—C2—H2A	120.3	N4—C11—C12	123.4 (2)
C3—C2—H2A	120.3	N4—C11—H11A	118.3
C2—C3—C4	117.9 (3)	C12—C11—H11A	118.3
C2—C3—C6	119.5 (2)	C11—C12—C8	118.9 (3)
C4—C3—C6	122.6 (2)	C11—C12—H12A	120.5
C5—C4—C3	119.3 (3)	C8—C12—H12A	120.5
C5—C4—H4A	120.3

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

Experimental details

Crystal data
Chemical formula	[ZnCl₂(C₁₂H₈N₄S)]
M_r	376.55
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	12.9990 (13), 5.4039 (5), 20.195 (2)
β (°)	101.459 (4)
V (Å³)	1390.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.29
Crystal size (mm)	0.20 × 0.12 × 0.04

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2002)
T_min, T_max	0.690, 0.912
No. of measured, independent and observed [I > 2σ(I)] reflections	10073, 3155, 2688
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.089, 1.04
No. of reflections	3155
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.38

Computer programs: CrystalClear (Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999).

Selected geometric parameters (Å, º) top

Zn1—N4ⁱ	2.060 (2)	Zn1—Cl1	2.1939 (8)
Zn1—N1	2.060 (2)	Zn1—Cl2	2.2402 (8)

N4ⁱ—Zn1—N1	103.11 (9)	N4ⁱ—Zn1—Cl2	104.00 (7)
N4ⁱ—Zn1—Cl1	107.44 (6)	N1—Zn1—Cl2	104.64 (6)
N1—Zn1—Cl1	107.78 (7)	Cl1—Zn1—Cl2	127.44 (3)

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

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