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

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catena-Poly[[(5,5′-di­methyl-2,2′-bi­pyridine-κ2N,N′)cadmium(II)]-di-μ-iodido]

aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran
*Correspondence e-mail: v_amani2002@yahoo.com

(Received 11 April 2010; accepted 16 April 2010; online 24 April 2010)

In the title coordination polymer, [CdI2(C12H12N2)]n, the Cd2+ ion lies on a twofold rotation axis: it is six-coordinated in a distorted cis-CdN2I4 octa­hedral geometry by two N atoms from a chelating 5,5′-dimethyl-2,2′-bipyridine ligands and four bridging iodide anions. The bridging function of the iodide ions leads to a chain structure propagating in [001].

Related literature

For related structures, see: Ahmadi et al. (2008[Ahmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233.]); Albada et al. (2004[Albada, G. A., Mohamadou, A., Mutikainen, I., Turpeinen, U. & Reedijk, J. (2004). Eur. J. Inorg. Chem. pp. 3733-3742.]); Amani et al. (2007[Amani, V., Safari, N. & Khavasi, H. R. (2007). Polyhedron, 26, 4257-4262.], 2009[Amani, V., Safari, N., Khavasi, H. R. & Akkurt, M. (2009). Polyhedron, 28, 3026-3030.]); Chattopadhyay et al. (2008[Chattopadhyay, T., Banerjee, A., Banu, K. S., Suresh, E., Netahji, M., Birarda, G., Zangrando, E. & Das, D. (2008). Polyhedron, 27, 2452-2458.]); Guo et al. (2006[Guo, H.-X., Yang, L.-M., Lin, Z.-X. & Zou, X.-J. (2006). Acta Cryst. E62, m2863-m2865.]); Kalateh et al. (2008[Kalateh, K., Ahmadi, R., Ebadi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1353-m1354.], 2010[Kalateh, K., Ahmadi, R. & Amani, V. (2010). Acta Cryst. E66, m512.]); Khalighi et al. (2008[Khalighi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1211-m1212.]); Maheshwari et al. (2007[Maheshwari, V., Carlone, M., Fronczek, F. R. & Marzilli, L. G. (2007). Acta Cryst. B63, 603-611.]); Tadayon Pour et al. (2008[Tadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305.]); Yu et al. (2007[Yu, J. H., Ye, L., Bi, M. H., Hou, Q., Zhang, X. & Xu, J. Q. (2007). Inorg. Chim. Acta, 360, 1987-1994.]).

[Scheme 1]

Experimental

Crystal data
  • [CdI2(C12H12N2)]

  • Mr = 550.45

  • Monoclinic, C 2/c

  • a = 19.086 (4) Å

  • b = 10.057 (2) Å

  • c = 7.8451 (16) Å

  • β = 101.80 (3)°

  • V = 1474.0 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 5.65 mm−1

  • T = 298 K

  • 0.25 × 0.15 × 0.12 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS, Madison, Wisconsin, USA.]) Tmin = 0.380, Tmax = 0.510

  • 8294 measured reflections

  • 1981 independent reflections

  • 1832 reflections with I > 2σ(I)

  • Rint = 0.062

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.098

  • S = 1.23

  • 1981 reflections

  • 79 parameters

  • H-atom parameters constrained

  • Δρmax = 1.30 e Å−3

  • Δρmin = −1.43 e Å−3

Table 1
Selected bond lengths (Å)

Cd1—N1 2.347 (3)
Cd1—I1 2.8586 (7)
Cd1—I1i 3.1628 (8)
Symmetry code: (i) [x, -y+1, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS, Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS, Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

In a recent paper, we reported the synthes and crystal structure of [Cd(5,5'-dmbpy)(µ-Cl)2]n, (Ahmadi et al., 2008) and [Cd(4,4'-dmbpy)(DMSO)I2], (Kalateh et al., 2010) [where 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine and 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine].

5,5'-Dimethyl-2,2'-bipyridine (5,5'-dmbipy), is a good bidentate ligand, and numerous complexes with 5,5'-dmbipy have been prepared, such as that of zinc (Khalighi et al., 2008), indium (Kalateh et al., 2008), iron (Amani et al., 2007), platin (Amani et al., 2009; Maheshwari et al., 2007), copper (Albada et al., 2004) and mercury (Tadayon Pour et al., 2008).

There are several CdII polymer complexes, with formula, [Cd(N—N)(µ-I)2]n, such as [Cd(phen)(µ-I)2]n, (Guo et al., 2006), [Cd(bipy)(µ-I)2]n, (Yu et al., 2007) and [Cd(ampy)(µ-I)2]n, (Chattopadhyay et al., 2008) [where phen is 1,10-phenanthroline , bipy is 2,2'-bipyridine and ampy is 2-aminomethylpyridine] have been synthesized and characterized by single-crystal X-ray diffraction methods. Here, we report the synthesis and structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), contains one half -molecule; a twofold rotation axis passes through the Cd atom. The CdII atom is six-coordinated in a distorted octahedral configuration by two N atoms from 5,5'-dimethyl-2,2'-bipyridine and four bridging I atoms. The bridging function of the iodo atoms leads to a one-dimensional chain structure. The Cd—I and Cd—N bond lengths and angles (Table 1) are within normal range [Cd(phen)(µ-I)2]n, (Guo et al., 2006) and [Cd(bipy)(µ-I)2]n, (Yu et al., 2007).

Related literature top

For related structures, see: Ahmadi et al. (2008); Albada et al. (2004); Amani et al. (2007, 2009); Chattopadhyay et al. (2008); Guo et al. (2006); Kalateh et al. (2008, 2010); Khalighi et al. (2008); Maheshwari et al. (2007); Tadayon Pour, Ebadi, Abedi, Amani & Khavasi (2008); Yu et al. (2007).

Experimental top

A solution of 5,5'-dimethyl-2,2'-bipyridine (0.25 g, 1.33 mmol) in methanol (10 ml) was added to a solution of CdI2 (0.49 g, 1.33 mmol) in methanol (10 ml) at room temperature. Colourless blocks of (I) were obtained by methanol diffusion to a colorless solution in DMSO. Suitable crystals were isolated after one week (yield; 0.52 g, 71.0%).

Refinement top

All H atoms were positioned geometrically, with C—H = 0.93Å and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq.

Structure description top

In a recent paper, we reported the synthes and crystal structure of [Cd(5,5'-dmbpy)(µ-Cl)2]n, (Ahmadi et al., 2008) and [Cd(4,4'-dmbpy)(DMSO)I2], (Kalateh et al., 2010) [where 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine and 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine].

5,5'-Dimethyl-2,2'-bipyridine (5,5'-dmbipy), is a good bidentate ligand, and numerous complexes with 5,5'-dmbipy have been prepared, such as that of zinc (Khalighi et al., 2008), indium (Kalateh et al., 2008), iron (Amani et al., 2007), platin (Amani et al., 2009; Maheshwari et al., 2007), copper (Albada et al., 2004) and mercury (Tadayon Pour et al., 2008).

There are several CdII polymer complexes, with formula, [Cd(N—N)(µ-I)2]n, such as [Cd(phen)(µ-I)2]n, (Guo et al., 2006), [Cd(bipy)(µ-I)2]n, (Yu et al., 2007) and [Cd(ampy)(µ-I)2]n, (Chattopadhyay et al., 2008) [where phen is 1,10-phenanthroline , bipy is 2,2'-bipyridine and ampy is 2-aminomethylpyridine] have been synthesized and characterized by single-crystal X-ray diffraction methods. Here, we report the synthesis and structure of the title compound.

The asymmetric unit of the title compound, (Fig. 1), contains one half -molecule; a twofold rotation axis passes through the Cd atom. The CdII atom is six-coordinated in a distorted octahedral configuration by two N atoms from 5,5'-dimethyl-2,2'-bipyridine and four bridging I atoms. The bridging function of the iodo atoms leads to a one-dimensional chain structure. The Cd—I and Cd—N bond lengths and angles (Table 1) are within normal range [Cd(phen)(µ-I)2]n, (Guo et al., 2006) and [Cd(bipy)(µ-I)2]n, (Yu et al., 2007).

For related structures, see: Ahmadi et al. (2008); Albada et al. (2004); Amani et al. (2007, 2009); Chattopadhyay et al. (2008); Guo et al. (2006); Kalateh et al. (2008, 2010); Khalighi et al. (2008); Maheshwari et al. (2007); Tadayon Pour, Ebadi, Abedi, Amani & Khavasi (2008); Yu et al. (2007).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Fragment of a polymeric chain in (I) with displacement ellipsoids drawn at the 50% probability level. [Symmetry code: (a) -x+1, y, -z+5/2].
catena-Poly[[(5,5'-dimethyl-2,2'-bipyridine- κ2N,N')cadmium(II)]-di-µ-iodido] top
Crystal data top
[CdI2(C12H12N2)]F(000) = 1008
Mr = 550.45Dx = 2.480 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 351 reflections
a = 19.086 (4) Åθ = 2.2–29.3°
b = 10.057 (2) ŵ = 5.65 mm1
c = 7.8451 (16) ÅT = 298 K
β = 101.80 (3)°Block, colorless
V = 1474.0 (5) Å30.25 × 0.15 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
1981 independent reflections
Radiation source: fine-focus sealed tube1832 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
phi and ω scansθmax = 29.3°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 2626
Tmin = 0.380, Tmax = 0.510k = 1312
8294 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.23 w = 1/[σ2(Fo2) + (0.0571P)2 + 0.4175P]
where P = (Fo2 + 2Fc2)/3
1981 reflections(Δ/σ)max = 0.037
79 parametersΔρmax = 1.30 e Å3
0 restraintsΔρmin = 1.43 e Å3
Crystal data top
[CdI2(C12H12N2)]V = 1474.0 (5) Å3
Mr = 550.45Z = 4
Monoclinic, C2/cMo Kα radiation
a = 19.086 (4) ŵ = 5.65 mm1
b = 10.057 (2) ÅT = 298 K
c = 7.8451 (16) Å0.25 × 0.15 × 0.12 mm
β = 101.80 (3)°
Data collection top
Bruker SMART CCD
diffractometer
1981 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
1832 reflections with I > 2σ(I)
Tmin = 0.380, Tmax = 0.510Rint = 0.062
8294 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.23Δρmax = 1.30 e Å3
1981 reflectionsΔρmin = 1.43 e Å3
79 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 > 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
xyzUiso*/Ueq
C10.3791 (2)0.7656 (5)1.0047 (5)0.0482 (9)
H10.36150.68250.96520.058*
C20.3413 (3)0.8765 (5)0.9329 (6)0.0546 (11)
C30.2732 (3)0.8623 (8)0.7991 (8)0.0758 (17)
H3A0.27920.90200.69170.114*
H3B0.23500.90620.83950.114*
H3C0.26190.76980.78070.114*
C40.3706 (3)0.9988 (5)0.9920 (6)0.0590 (12)
H40.34781.07670.94730.071*
C50.4327 (3)1.0059 (5)1.1151 (6)0.0545 (10)
H50.45211.08811.15310.065*
C60.4666 (2)0.8885 (4)1.1833 (5)0.0398 (8)
N10.43894 (18)0.7698 (3)1.1264 (4)0.0414 (7)
Cd10.50000.57933 (4)1.25000.04719 (14)
I10.407345 (14)0.39302 (3)1.03947 (3)0.04393 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.049 (2)0.048 (2)0.0463 (19)0.0039 (18)0.0055 (16)0.0064 (16)
C20.050 (2)0.066 (3)0.051 (2)0.013 (2)0.0171 (18)0.019 (2)
C30.054 (3)0.100 (5)0.071 (3)0.012 (3)0.005 (2)0.027 (3)
C40.074 (3)0.049 (3)0.058 (2)0.021 (2)0.023 (2)0.015 (2)
C50.077 (3)0.035 (2)0.055 (2)0.012 (2)0.023 (2)0.0084 (17)
C60.051 (2)0.0328 (18)0.0388 (17)0.0020 (14)0.0168 (15)0.0021 (12)
N10.0470 (17)0.0366 (17)0.0400 (14)0.0018 (13)0.0074 (12)0.0052 (12)
Cd10.0564 (3)0.0300 (2)0.0463 (2)0.0000.01021 (18)0.000
I10.04992 (19)0.03831 (18)0.04068 (17)0.00834 (9)0.00254 (11)0.00433 (8)
Geometric parameters (Å, º) top
C1—N11.331 (6)C5—H50.9300
C1—C21.384 (6)C6—N11.344 (5)
C1—H10.9300C6—C6i1.474 (9)
C2—C41.391 (8)Cd1—N12.347 (3)
C2—C31.501 (8)Cd1—N1i2.347 (3)
C3—H3A0.9600Cd1—I12.8586 (7)
C3—H3B0.9600Cd1—I1i2.8586 (7)
C3—H3C0.9600Cd1—I1ii3.1628 (8)
C4—C51.369 (9)Cd1—I1iii3.1629 (8)
C4—H40.9300I1—Cd1iii3.1629 (8)
C5—C61.399 (6)
N1—C1—C2124.4 (5)C5—C6—C6i122.5 (3)
N1—C1—H1117.8C1—N1—C6119.2 (4)
C2—C1—H1117.8C1—N1—Cd1123.4 (3)
C1—C2—C4115.8 (5)C6—N1—Cd1117.3 (3)
C1—C2—C3120.8 (5)N1i—Cd1—N170.55 (18)
C4—C2—C3123.3 (5)N1i—Cd1—I1165.97 (9)
C2—C3—H3A109.5N1—Cd1—I195.74 (9)
C2—C3—H3B109.5N1i—Cd1—I1i95.74 (9)
H3A—C3—H3B109.5N1—Cd1—I1i165.97 (9)
C2—C3—H3C109.5I1—Cd1—I1i98.09 (3)
H3A—C3—H3C109.5N1i—Cd1—I1ii86.26 (8)
H3B—C3—H3C109.5N1—Cd1—I1ii85.51 (8)
C5—C4—C2120.9 (4)I1—Cd1—I1ii95.844 (16)
C5—C4—H4119.6I1i—Cd1—I1ii90.771 (16)
C2—C4—H4119.6N1i—Cd1—I1iii85.51 (8)
C4—C5—C6119.4 (5)N1—Cd1—I1iii86.26 (8)
C4—C5—H5120.3I1—Cd1—I1iii90.771 (16)
C6—C5—H5120.3I1i—Cd1—I1iii95.842 (16)
N1—C6—C5120.2 (4)I1ii—Cd1—I1iii169.91 (2)
N1—C6—C6i117.4 (2)Cd1—I1—Cd1iii89.229 (16)
N1—C1—C2—C41.8 (7)C6—N1—Cd1—N1i0.26 (19)
N1—C1—C2—C3178.5 (4)C1—N1—Cd1—I12.9 (3)
C1—C2—C4—C50.7 (7)C6—N1—Cd1—I1177.2 (3)
C3—C2—C4—C5179.6 (5)C1—N1—Cd1—I1i167.5 (2)
C2—C4—C5—C60.5 (7)C6—N1—Cd1—I1i12.3 (5)
C4—C5—C6—N10.9 (6)C1—N1—Cd1—I1ii92.5 (3)
C4—C5—C6—C6i179.7 (4)C6—N1—Cd1—I1ii87.4 (3)
C2—C1—N1—C61.5 (6)C1—N1—Cd1—I1iii93.3 (3)
C2—C1—N1—Cd1178.4 (3)C6—N1—Cd1—I1iii86.8 (3)
C5—C6—N1—C10.1 (6)N1i—Cd1—I1—Cd1iii74.4 (3)
C6i—C6—N1—C1179.4 (4)N1—Cd1—I1—Cd1iii86.32 (8)
C5—C6—N1—Cd1179.8 (3)I1i—Cd1—I1—Cd1iii96.013 (15)
C6i—C6—N1—Cd10.7 (5)I1ii—Cd1—I1—Cd1iii172.370 (15)
C1—N1—Cd1—N1i179.8 (4)I1iii—Cd1—I1—Cd1iii0.0
Symmetry codes: (i) x+1, y, z+5/2; (ii) x, y+1, z+1/2; (iii) x+1, y+1, z+2.

Experimental details

Crystal data
Chemical formula[CdI2(C12H12N2)]
Mr550.45
Crystal system, space groupMonoclinic, C2/c
Temperature (K)298
a, b, c (Å)19.086 (4), 10.057 (2), 7.8451 (16)
β (°) 101.80 (3)
V3)1474.0 (5)
Z4
Radiation typeMo Kα
µ (mm1)5.65
Crystal size (mm)0.25 × 0.15 × 0.12
Data collection
DiffractometerBruker SMART CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.380, 0.510
No. of measured, independent and
observed [I > 2σ(I)] reflections
8294, 1981, 1832
Rint0.062
(sin θ/λ)max1)0.688
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.098, 1.23
No. of reflections1981
No. of parameters79
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.30, 1.43

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top
Cd1—N12.347 (3)Cd1—I1i3.1628 (8)
Cd1—I12.8586 (7)
Symmetry code: (i) x, y+1, z+1/2.
 

Acknowledgements

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch for financial support.

References

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