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Acta Cryst. (2009). E65, m235    [ doi:10.1107/S1600536809002736 ]

Bis(phenanthridinium) hexachloridoplatinate(IV) dimethyl sulfoxide disolvate

S. Karaca, M. Akkurt, N. Safari, V. Amani, O. Büyükgüngör and A. Abedi

Abstract top

The asymmetric unit of the title compound, (C13H10N)2[PtCl6]·2C2H6OS, contains one independent protonated phenanthridinium cation, half of a centrosymmetric [PtCl6]2-anion and one dimethyl sulfoxide solvent molecule. Intramolecular N-H...O and intermolecular C-H...Cl hydrogen-bonding interactions seem to be effective in the stabilization of the structure.

Comment top

In recent years, there has been considerable interest in proton transfer systems and their structures (Zafar et al., 2000; Abedi et al., 2008). Several proton transfer systems using H2[PtCl6] with proton acceptor molecules, such as [HpyBr-3]2[PtCl6].2H2O, (II), and [HpyI-3]2[PtCl6].2H2O, (III), (Zordan et al., 2005), [BMIM]2[PtCl6], (IV), and [EMIM]2[PtCl6], (V), (Hasan et al., 2001), {(DABCO)H2[PtCl6]}, (VI), (Juan et al.,1998), {p-C6H4(CH2ImMe)2[PtCl6]}, (VII), (Li & Liu, 2003), [het][PtCl6].2H2O, (VIII), (Hu et al., 2003), [9-MeGuaH]2[PtCl6].2H2O, (IX), (Terzis & Mentzafos, 1983), [HpyCl-3]3[PtCl6]Cl, (X), (Zordan et al., 2004), [2,9-dmphen.H]2[PtCl6], (XI), (Yousefi et al., 2007), [H2DA18C6][PtCl6].2H2O, (XII), (Yousefi et al., 2007a), [2,6-dmpy.H]2[PtCl6], (XIII), (Amani et al., 2008), [TBA]3[PtCl6]Cl, (XIV), (Yousefi et al., 2007b) and [2,4,6-dmpy.H]2[PtCl6], (XV), (Kalateh et al., 2008) [where hpy is halo-pyridinium, BMIM+ is 1-n-butyl-3-methylimidazolium, EMIM+ is1-ethyl-3-methylimidazolium, DABCO is 1,4-diazabicyclooctane, Im is imidazolium, het is 2-(α-hydroxyethyl) thiamine, 9-MeGuaH is 9-methylguaninium, 2,9-dmphen.H is 2,9-dimethyl-1,10-phenanthrolinium, H2DA18C6 is 1,10-Diazonia-18-crown-6,2,6-dmpy.H is 2,6-dimethylpyridinium, TBA is tribenzylammonium and 2,4,6-dmpy.H is 2,4,6-dimethylpyridinium] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

The asymmetric unit of the title compound (I), (Fig. 1) contains one independent protonated phenanthridinium cation and one half PtCl2-6 anion, and one dimethyl sulfoxide solvate. The Pt ion has an octahedral coordination (Table 1). In cation, the bond lengths and angles are normal. In PtCl2-6 anion, the Pt—Cl bond lengths and Cl—Pt—Cl bond angles are also within normal ranges, as in (III) to (XV).

The intramolecular N—H···O and intermolecular C—H···Cl hydrogen bonding interactions (Table 1) seem to be effective in the stabilization of the structure (Fig. 2).

Related literature top

For related literature, see: Abedi et al. (2008); Amani et al. (2008); Hasan et al. (2001); Hu et al. (2003); Juan et al. (1998); Kalateh et al. (2008); Li & Liu (2003); Terzis & Mentzafos (1983); Yousefi, Ahmadi et al. (2007); Yousefi, Teimouri et al. (2007a,b); Zafar et al. (2000); Zordan & Brammer (2004); Zordan et al. (2005).

Experimental top

For the preparation of the title compound, (I), a solution of phenanthridine (0.27 g,1.48 mmol) in ethanol (10 ml) was added to a solution of H2PtCl6.6H2O, (0.38 g, 0.74 mmol) in ethanol (10 ml) at room temperature. The suitable crystals for X-ray diffraction experiment were obtained by ethanol diffusion in a solution of orange precipitated in DMSO after one week [yield; 0.51 g, 74.7%, m.p. < 573 K].

Refinement top

The C-bound H-atoms were placed in calculated positions with C—H = 0.93 Å and C—H 0.96 Å, and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2Ueq (ring C) and Uiso(H) = 1.5Ueq (methyl C). The N-bound H-atom was found from a difference Fourier map and refined freely. In the final Fourier map, the highest and deepest peaks were located 1.13 and 0.47 Å from atom S1, respectively.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. ORTEP-3 view of the title molecule, with the atom-numbering scheme and 50% probability displacement ellipsoids
[Figure 2] Fig. 2. View of the packing and hydrogen bonding interactions. For clarity, H atoms not involved in hydrogen bonds have been omitted.
Bis(phenanthridinium) hexachloridoplatinate(IV) dimethyl sulfoxide disolvate top
Crystal data top
(C13H10N)2[PtCl6]·2C2H6OSF(000) = 1816
Mr = 924.50Dx = 1.828 Mg m−3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 46774 reflections
a = 24.3695 (11) Åθ = 1.4–27.3°
b = 7.9061 (3) ŵ = 4.81 mm−1
c = 17.4322 (6) ÅT = 295 K
V = 3358.6 (2) Å3Prism, yellow
Z = 40.80 × 0.35 × 0.09 mm
Data collection top
Stoe IPDS-2
diffractometer		3533 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2992 reflections with I > 2σ(I)
plane graphiteRint = 0.106
Detector resolution: 6.67 pixels mm-1θmax = 26.8°, θmin = 1.7°
ω scansh = −30→30
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −9→10
Tmin = 0.114, Tmax = 0.671l = −22→20
33029 measured reflections
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0192P)2 + 15.6678P]
where P = (Fo2 + 2Fc2)/3
3533 reflections(Δ/σ)max = 0.001
199 parametersΔρmax = 2.20 e Å−3
0 restraintsΔρmin = −1.01 e Å−3
Crystal data top
(C13H10N)2[PtCl6]·2C2H6OSV = 3358.6 (2) Å3
Mr = 924.50Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 24.3695 (11) ŵ = 4.81 mm−1
b = 7.9061 (3) ÅT = 295 K
c = 17.4322 (6) Å0.80 × 0.35 × 0.09 mm
Data collection top
Stoe IPDS-2
diffractometer		3533 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		2992 reflections with I > 2σ(I)
Tmin = 0.114, Tmax = 0.671Rint = 0.106
33029 measured reflectionsθmax = 26.8°
Refinement top
R[F2 > 2σ(F2)] = 0.045 w = 1/[σ2(Fo2) + (0.0192P)2 + 15.6678P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096Δρmax = 2.20 e Å−3
S = 1.12Δρmin = −1.01 e Å−3
3533 reflectionsAbsolute structure: ?
199 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
H atoms treated by a mixture of independent and constrained refinement
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
N10.3026 (2)0.7872 (7)0.9147 (3)0.0450 (17)
C10.2284 (2)0.9236 (7)0.8111 (3)0.0380 (17)
C20.1935 (3)0.9962 (8)0.7558 (4)0.051 (2)
C30.2148 (3)1.0700 (9)0.6916 (4)0.057 (3)
C40.2715 (3)1.0779 (9)0.6797 (4)0.059 (3)
C50.3067 (3)1.0107 (9)0.7327 (4)0.052 (2)
C60.2855 (2)0.9333 (8)0.7987 (3)0.0417 (17)
C70.3209 (3)0.8621 (8)0.8539 (4)0.048 (2)
C80.2463 (3)0.7702 (8)0.9301 (3)0.0403 (17)
C90.2309 (3)0.6859 (9)0.9972 (4)0.049 (2)
C100.1764 (3)0.6683 (9)1.0126 (4)0.056 (2)
C110.1378 (3)0.7337 (9)0.9637 (5)0.060 (3)
C120.1527 (3)0.8186 (8)0.8981 (4)0.051 (2)
C130.2085 (2)0.8394 (7)0.8797 (3)0.0383 (17)
S10.42059 (10)0.6422 (3)1.04509 (15)0.0776 (8)
O10.3643 (2)0.7031 (10)1.0318 (4)0.099 (3)
C140.4292 (4)0.6686 (12)1.1452 (5)0.080 (3)
C150.4641 (5)0.7984 (15)1.0151 (6)0.111 (5)
Pt11.000000.67772 (4)0.250000.0358 (1)
Cl10.95124 (7)0.8825 (2)0.18305 (10)0.0533 (5)
Cl21.04739 (6)0.4687 (2)0.31590 (9)0.0509 (5)
Cl31.06735 (7)0.6805 (2)0.15568 (9)0.0525 (5)
HN10.325 (4)0.753 (11)0.948 (5)0.09 (3)*
H20.155700.993800.763000.0610*
H30.191201.115800.655200.0690*
H40.285201.128900.635600.0710*
H50.344401.016400.724900.0620*
H70.358600.869200.846400.0580*
H90.257200.642901.030500.0590*
H100.165300.611501.056600.0670*
H110.100700.720300.975100.0710*
H120.125900.862500.865800.0610*
H14A0.406700.588101.172000.1200*
H14B0.418400.781101.159500.1200*
H14C0.467000.651001.158500.1200*
H15A0.464700.801500.960100.1660*
H15B0.500400.776001.034000.1660*
H15C0.451700.905401.034500.1660*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.030 (3)0.053 (3)0.052 (3)−0.001 (2)−0.008 (2)−0.008 (3)
C10.036 (3)0.037 (3)0.041 (3)0.002 (2)−0.004 (2)−0.009 (2)
C20.043 (3)0.056 (4)0.054 (4)0.007 (3)−0.005 (3)−0.007 (3)
C30.062 (5)0.059 (4)0.051 (4)0.011 (4)−0.007 (4)−0.001 (3)
C40.074 (5)0.057 (4)0.046 (4)0.004 (4)0.013 (4)0.000 (3)
C50.051 (4)0.061 (4)0.044 (4)−0.005 (3)0.008 (3)−0.009 (3)
C60.034 (3)0.047 (3)0.044 (3)0.005 (3)0.001 (3)−0.013 (3)
C70.026 (3)0.057 (4)0.061 (4)0.002 (3)−0.002 (3)−0.012 (3)
C80.036 (3)0.043 (3)0.042 (3)0.002 (3)−0.001 (3)−0.013 (3)
C90.053 (4)0.053 (4)0.042 (3)−0.002 (3)−0.006 (3)−0.004 (3)
C100.059 (4)0.055 (4)0.053 (4)−0.005 (4)0.006 (4)0.000 (3)
C110.040 (4)0.061 (4)0.078 (5)0.000 (3)0.018 (4)0.003 (4)
C120.035 (3)0.054 (4)0.064 (4)0.005 (3)0.002 (3)0.000 (3)
C130.032 (3)0.041 (3)0.042 (3)0.004 (2)−0.001 (2)−0.013 (3)
S10.0602 (13)0.0891 (16)0.0836 (15)−0.0018 (11)−0.0189 (11)−0.0056 (12)
O10.049 (3)0.170 (7)0.077 (4)0.013 (4)−0.021 (3)0.027 (4)
C140.072 (6)0.106 (7)0.062 (5)−0.016 (5)−0.017 (4)0.030 (5)
C150.095 (8)0.166 (11)0.071 (6)−0.051 (8)0.009 (6)−0.023 (7)
Pt10.0247 (2)0.0484 (2)0.0342 (2)0.00000.0005 (1)0.0000
Cl10.0434 (9)0.0616 (9)0.0548 (9)0.0150 (8)−0.0025 (7)0.0076 (8)
Cl20.0390 (8)0.0611 (9)0.0527 (9)0.0007 (7)−0.0073 (7)0.0160 (8)
Cl30.0396 (8)0.0715 (10)0.0463 (8)0.0082 (8)0.0145 (7)0.0067 (8)
Geometric parameters (Å, °) top
Pt1—Cl1i2.3228 (17)C8—C131.386 (8)
Pt1—Cl2i2.3204 (16)C9—C101.362 (10)
Pt1—Cl3i2.3233 (16)C10—C111.371 (11)
Pt1—Cl32.3233 (16)C11—C121.375 (11)
Pt1—Cl12.3228 (17)C12—C131.407 (9)
Pt1—Cl22.3204 (16)C2—H20.9300
S1—C141.770 (9)C3—H30.9300
S1—C151.710 (12)C4—H40.9300
S1—O11.472 (6)C5—H50.9300
N1—C71.293 (9)C7—H70.9300
N1—C81.405 (9)C9—H90.9300
N1—HN10.84 (9)C10—H100.9300
C1—C61.410 (7)C11—H110.9300
C1—C21.408 (9)C12—H120.9300
C1—C131.452 (7)C14—H14B0.9600
C2—C31.365 (10)C14—H14A0.9600
C3—C41.399 (10)C14—H14C0.9600
C4—C51.368 (10)C15—H15C0.9600
C5—C61.402 (9)C15—H15A0.9600
C6—C71.410 (9)C15—H15B0.9600
C8—C91.398 (9)
Cl1···Cl1i3.331 (2)C8···O13.420 (9)
Cl1···Cl2i3.272 (2)C8···C6ix3.598 (8)
Cl1···Cl3i3.265 (2)C8···C9viii3.533 (9)
Cl1···Cl33.284 (2)C8···C1ix3.492 (8)
Cl2···Cl1i3.272 (2)C9···O13.309 (9)
Cl2···Cl3i3.297 (2)C9···C8ix3.533 (9)
Cl2···Cl33.293 (2)C10···Cl3xi3.646 (7)
Cl2···C7ii3.540 (7)C13···C6ix3.511 (8)
Cl2···Cl2i3.258 (2)C2···H122.7400
Cl3···Cl23.293 (2)C2···H14Axii2.9200
Cl3···Cl13.284 (2)C4···H10xii3.0400
Cl3···Cl1i3.265 (2)C10···H3xiii3.0400
Cl3···C10iii3.646 (7)C12···H22.7300
Cl3···Cl2i3.297 (2)HN1···H92.3600
Cl1···H15Aiv2.9100HN1···S13.01 (9)
Cl1···H14Cv2.9400HN1···O11.79 (9)
Cl1···H2vi2.9400H2···H122.1900
Cl1···H7iv3.0500H2···H14Axii2.2900
Cl1···H12vi2.8900H2···C122.7300
Cl2···H7ii2.6800H2···Cl1vi2.9400
Cl2···H15Aii3.1200H3···C10xiv3.0400
Cl2···H5ii3.0800H5···H72.4400
Cl3···H15Cvii3.0700H5···Cl2x3.0800
Cl3···H10iii3.0000H5···Cl3x2.9200
Cl3···H5ii2.9200H7···Cl1xv3.0500
S1···HN13.01 (9)H7···H52.4400
O1···N12.621 (8)H7···Cl2x2.6800
O1···C93.309 (9)H9···O12.6500
O1···C83.420 (9)H9···HN12.3600
O1···HN11.79 (9)H10···C4xvi3.0400
O1···H92.6500H10···Cl3xi3.0000
N1···O12.621 (8)H11···H15Bxvii2.4500
C1···C8viii3.492 (8)H12···C22.7400
C1···C4ix3.566 (9)H12···H22.1900
C2···C7viii3.379 (9)H12···Cl1vi2.8900
C2···C6viii3.573 (9)H14A···C2xvi2.9200
C3···C6viii3.426 (9)H14A···H2xvi2.2900
C3···C5viii3.596 (10)H14B···H15C2.5200
C4···C1viii3.566 (9)H14C···H15B2.5200
C5···C3ix3.596 (10)H14C···Cl1xviii2.9400
C6···C3ix3.426 (9)H15A···Cl2x3.1200
C6···C13viii3.511 (8)H15A···Cl1xv2.9100
C6···C2ix3.573 (9)H15B···H14C2.5200
C6···C8viii3.598 (8)H15B···H11xix2.4500
C7···C2ix3.379 (9)H15C···H14B2.5200
C7···Cl2x3.540 (7)H15C···Cl3xx3.0700
Cl1i—Pt1—Cl289.60 (6)C9—C10—C11120.5 (7)
Cl2—Pt1—Cl2i89.18 (6)C10—C11—C12121.4 (7)
Cl2—Pt1—Cl3i90.46 (5)C11—C12—C13120.1 (6)
Cl1i—Pt1—Cl389.29 (6)C1—C13—C8118.8 (5)
Cl2i—Pt1—Cl390.46 (5)C1—C13—C12124.4 (5)
Cl3—Pt1—Cl3i178.92 (6)C8—C13—C12116.9 (5)
Cl1i—Pt1—Cl2i178.75 (6)C1—C2—H2120.00
Cl1i—Pt1—Cl3i89.96 (6)C3—C2—H2120.00
Cl2i—Pt1—Cl3i90.32 (5)C2—C3—H3119.00
Cl2—Pt1—Cl390.32 (5)C4—C3—H3120.00
Cl1—Pt1—Cl1i91.62 (6)C3—C4—H4120.00
Cl1—Pt1—Cl2178.75 (6)C5—C4—H4120.00
Cl1—Pt1—Cl389.96 (6)C6—C5—H5120.00
Cl1—Pt1—Cl2i89.60 (6)C4—C5—H5120.00
Cl1—Pt1—Cl3i89.29 (6)N1—C7—H7119.00
O1—S1—C14103.1 (4)C6—C7—H7119.00
O1—S1—C15107.1 (5)C8—C9—H9121.00
C14—S1—C1598.2 (5)C10—C9—H9121.00
C7—N1—C8122.5 (5)C11—C10—H10120.00
C8—N1—HN1118 (6)C9—C10—H10120.00
C7—N1—HN1119 (6)C12—C11—H11119.00
C2—C1—C13123.3 (5)C10—C11—H11119.00
C2—C1—C6118.0 (5)C13—C12—H12120.00
C6—C1—C13118.7 (5)C11—C12—H12120.00
C1—C2—C3120.4 (6)S1—C14—H14A109.00
C2—C3—C4121.1 (7)S1—C14—H14B109.00
C3—C4—C5120.1 (7)S1—C14—H14C110.00
C4—C5—C6119.5 (6)H14A—C14—H14B109.00
C1—C6—C5120.9 (5)H14A—C14—H14C110.00
C5—C6—C7120.6 (5)H14B—C14—H14C110.00
C1—C6—C7118.5 (5)S1—C15—H15A109.00
N1—C7—C6122.1 (6)S1—C15—H15B109.00
C9—C8—C13122.7 (6)S1—C15—H15C109.00
N1—C8—C9117.9 (6)H15A—C15—H15B109.00
N1—C8—C13119.4 (5)H15A—C15—H15C110.00
C8—C9—C10118.4 (7)H15B—C15—H15C109.00
C7—N1—C8—C9179.5 (6)C4—C5—C6—C10.1 (10)
C7—N1—C8—C13−1.7 (9)C4—C5—C6—C7179.6 (6)
C8—N1—C7—C60.4 (10)C1—C6—C7—N10.7 (9)
C6—C1—C2—C31.4 (9)C5—C6—C7—N1−178.8 (6)
C13—C1—C2—C3−178.4 (6)N1—C8—C9—C10−179.8 (6)
C13—C1—C6—C7−0.6 (8)C13—C8—C9—C101.4 (10)
C2—C1—C13—C8179.2 (6)N1—C8—C13—C11.7 (8)
C2—C1—C13—C121.0 (9)N1—C8—C13—C12−179.9 (5)
C6—C1—C13—C8−0.6 (8)C9—C8—C13—C1−179.5 (6)
C6—C1—C13—C12−178.8 (6)C9—C8—C13—C12−1.2 (9)
C2—C1—C6—C5−0.9 (9)C8—C9—C10—C11−0.8 (11)
C2—C1—C6—C7179.6 (6)C9—C10—C11—C12−0.1 (11)
C13—C1—C6—C5178.9 (6)C10—C11—C12—C130.3 (11)
C1—C2—C3—C4−1.1 (10)C11—C12—C13—C1178.6 (6)
C2—C3—C4—C50.2 (11)C11—C12—C13—C80.4 (9)
C3—C4—C5—C60.3 (10)
Symmetry codes: (i) −x+2, y, −z+1/2; (ii) −x+3/2, −y+3/2, z−1/2; (iii) x+1, y, z−1; (iv) x+1/2, −y+3/2, −z+1; (v) −x+3/2, y+1/2, z−1; (vi) −x+1, −y+2, −z+1; (vii) −x+3/2, y−1/2, z−1; (viii) −x+1/2, y+1/2, z; (ix) −x+1/2, y−1/2, z; (x) −x+3/2, −y+3/2, z+1/2; (xi) x−1, y, z+1; (xii) −x+1/2, −y+3/2, z−1/2; (xiii) x, −y+2, z+1/2; (xiv) x, −y+2, z−1/2; (xv) x−1/2, −y+3/2, −z+1; (xvi) −x+1/2, −y+3/2, z+1/2; (xvii) x−1/2, −y+3/2, −z+2; (xviii) −x+3/2, y−1/2, z+1; (xix) x+1/2, −y+3/2, −z+2; (xx) −x+3/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O10.84 (9)1.79 (9)2.621 (8)169 (8)
C7—H7···Cl2x0.932.683.540 (7)154
Symmetry codes: (x) −x+3/2, −y+3/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—HN1···O10.84 (9)1.79 (9)2.621 (8)169 (8)
C7—H7···Cl2i0.932.683.540 (7)154
Symmetry codes: (i) −x+3/2, −y+3/2, z+1/2.
Acknowledgements top

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for use of the Stoe IPDS II diffractometer (purchased under grant No. F.279 of the University Research Fund). N. Safari, V. Amani and A. Abedi are grateful to Shahid Beheshti University for financial support.

references
References top

Abedi, A., Bahrami Shabestari, A. & Amani, V. (2008). Acta Cryst. E64, o990.

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Amani, V., Rahimi, R. & Khavasi, H. R. (2008). Acta Cryst. E64, m1143–m1144.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Hasan, M., Kozhevnikov, I. V., Siddiqui, M. R. H., Femoni, C., Steiner, A. & Winterton, N. (2001). Inorg. Chem. 40, 795–800.

Hu, N. H., Norifusa, T. & Aoki, K. (2003). Dalton Trans. pp. 335–341.

Juan, C., Mareque, R. & Lee, B. (1998). Inorg. Chem. 37, 4756–4757.

Kalateh, K., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1267–m1268.

Li, D. & Liu, D. (2003). Anal. Sci. 19, 1089–1090.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

Terzis, A. & Mentzafos, D. (1983). Inorg. Chem. 22, 1140–1143.

Yousefi, M., Ahmadi, R., Amani, V. & Khavasi, H. R. (2007). Acta Cryst. E63, m3114–m3115.

Yousefi, M., Teimouri, S., Amani, V. & Khavasi, H. R. (2007a). Acta Cryst. E63, m2460–m2461.

Yousefi, M., Teimouri, S., Amani, V. & Khavasi, H. R. (2007b). Acta Cryst. E63, m2748–m2749.

Zafar, A., Geib, S. J., Hamuro, Y., Carr, A. J. & Hamilton, A. D. (2000). Tetrahedron, 56, 8419–8427.

Zordan, F. & Brammer, L. (2004). Acta Cryst. B60, 512–519.

Zordan, F., Purver, S. L., Adams, H. & Brammer, L. (2005). CrystEngComm, 7, 350–354.