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Redetermination of tetra­methyl tetra­thia­fulvalene-2,3,6,7-tetra­carboxyl­ate

aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
*Correspondence e-mail: edwin.weber@chemie.tu-freiberg.de

(Received 13 June 2012; accepted 28 June 2012; online 7 July 2012)

An improved crystal structure of the title compound, C14H12O8S4, is reported. The structure, previously solved using the heavy-atom method (R = 7.1%), has now been solved using direct methods. Due to the improved quality of the data set an R value of 2.06% could be achieved. In the crystal, C—H⋯S and C—H⋯O contacts link the mol­ecules.

Related literature

For the first structure determination of the title compound, see: Belsky & Voet (1976[Belsky, V. K. & Voet, D. (1976). Acta Cryst. B32, 272-274.]). For a previously reported experimental procedure and physical data, see: Yoneda et al. (1978[Yoneda, S., Kawase, T., Inaba, M. & Yoshida, Z. (1978). J. Org. Chem. 43, 595-598.]). For C—H⋯O hydrogen bonds, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc.]); Katzsch et al. (2011[Katzsch, F., Eissmann, D. & Weber, E. (2011). Struct. Chem. 23, 245-255.]); Fischer et al. (2011[Fischer, C., Gruber, T., Seichter, W. & Weber, E. (2011). Org. Biomol. Chem. 9, 4347-4352.]). For C—H⋯S hydrogen bonds, see: Mata et al. (2010[Mata, I., Alkorta, I., Molins, E. & Espinosa, E. (2010). Chem. Eur. J. 16, 2442-2452.]); Novoa et al. (1995[Novoa, J. J., Rovira, M. C., Rovira, C., Veciana, J. & Tarrés, J. (1995). Adv. Mater. 7, 233-237.]); Lu et al. (2005[Lu, W., Yan, Z.-M., Dai, J., Zhang, Y., Zhu, Q.-Y., Jia, D.-X. & Guo, W.-J. (2005). Inorg. Chem. pp. 2339-2345.]); Saad et al. (2010[Saad, A., Jeannin, O. & Fourmigue, M. (2010). CrystEngComm, 12, 3866-3874.]). For a description of ring motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.]); Petersen et al. (2007[Petersen, M. A., Zhu, L., Jensen, S. H., Anderson, A. S., Kadziola, A., Kilsa, K. & Nielsen, M. B. (2007). Adv. Funct. Mater. 17, 797-804.]). For several steps of the synthetic procedure, see: Degani et al. (1986[Degani, I., Fochi, R., Gatti, A. & Regondi, V. (1986). Synthesis, pp. 894-899.]); O'Connor & Jones (1970[O'Connor, B. R. & Jones, F. N. (1970). J. Org. Chem. 35, 2002-2005.]); Nguyen et al. (2010[Nguyen, T. L. A., Demir-Cakan, R., Devic, T., Morcrette, M., Ahnfeldt, T., Auban-Senzier, P., Stock, N., Goncalves, A.-M., Filinchuk, Y., Tarascon, J.-M. & Férey, G. (2010). Inorg. Chem. 49, 7135-7143.]). For general background to the electroconductive behaviour of tetra­thia­fulvalene derivatives, see: Takase et al. (2011[Takase, M., Yoshida, N., Nishinaga, T. & Iyoda, M. (2011). Org. Lett. 13, 3896-3899.]).

[Scheme 1]

Experimental

Crystal data
  • C14H12O8S4

  • Mr = 436.48

  • Triclinic, [P \overline 1]

  • a = 6.8666 (2) Å

  • b = 7.8783 (2) Å

  • c = 8.4335 (2) Å

  • α = 100.221 (1)°

  • β = 99.255 (1)°

  • γ = 99.328 (1)°

  • V = 434.53 (2) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.59 mm−1

  • T = 100 K

  • 0.64 × 0.16 × 0.15 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.705, Tmax = 0.917

  • 10884 measured reflections

  • 1534 independent reflections

  • 1471 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.021

  • wR(F2) = 0.055

  • S = 1.08

  • 1534 reflections

  • 120 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C7—H7A⋯S1i 0.96 2.83 3.735 (2) 158
C5—H5A⋯O1ii 0.96 2.50 3.324 (2) 143
C5—H5C⋯O3iii 0.96 2.65 3.481 (2) 145
Symmetry codes: (i) x, y, z-1; (ii) -x+2, -y+2, -z+2; (iii) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). SADABS, APEX2 and SAINT. AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SADABS, APEX2 and SAINT. AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Tetrathiafulvalene derivatives are molecules of high importance relating to electroconductive behaviour (Takase et al., 2011).

The present structure of the title compound (TTF) has been refined to an R-value of 2.06% which is clearly better than 7.1% of the previous study reported in 1976 by Belsky and Voet. In particular, this enabled us to refine the positions of hydrogen atoms of the methyl groups with improved accuracy making it possible to find potential hydrogen bonds. In conformity with previous findings, the TTF scaffold is planar and the methoxycarbonyl functions are slightly twisted out of the ring plane [interplanar angles 25.60 (1) and 42.77 (2)°] (Fig. 1).

The refinement shows the molecules being arranged in a layered structure (Fig. 2) stabilized by C—H···O (Desiraju et al., 1999; Katzsch et al., 2011; Fischer et al., 2011) and C—H···S contacts (Mata et al., 2010; Novoa et al., 1995) (Table 1). Two molecules each are associated forming special dimer type species (Fig. 2). In one case, they involve two ester functions [d(C5—H5A···O1) = 2.50 Å] giving rise to a hydrogen bonded ring motif R22(10) (Bernstein et al., 1995; Petersen et al., 2007). In the other case, adjacent molecules show hydrogen bonding interactions between ester methyl groups and sulfur atoms [d(C7—H7A···S1) = 2.83 Å] (Saad et al., 2010; Lu et al., 2005). The layers are also connected via C—H···O contacts including a methyl group and a carbonyl function [d(C5—H5C···O3) = 2.65 Å] of superimposed molecules.

Related literature top

For the first structure determination of the title compound, see: Belsky & Voet (1976). For a previously reported experimental procedure and physical data, see: Yoneda et al. (1978). For C—H···O hydrogen bonds, see: Desiraju & Steiner (1999); Katzsch et al. (2011); Fischer et al. (2011). For C—H···S hydrogen bonds, see: Mata et al. (2010); Novoa et al. (1995); Lu et al. (2005); Saad et al. (2010). For a description of ring motifs, see: Bernstein et al. (1995); Petersen et al. (2007). For several steps of the synthetic procedure, see: Degani et al. (1986); O'Connor & Jones (1970); Nguyen et al. (2010). For general background to the electroconductive behaviour of tetrathiafulvalene derivatives, see: Takase et al. (2011).

Experimental top

The titled tetramethyl tetrathiafulvalene-2,3,6,7-tetracarboxylate was synthesized via a four step reaction sequence: (1) 1,3-Dithiolane-2-thione was prepared from carbon disulfide, sodium sulfide and 1,2-dichloroethane under phase transfer catalyzed condition following literature protocol (I. Degani et al., 1986). (2) Reflux of 1,3-dithiolane-2-thione and dimethyl acetylenedicarboxylate in toluene yielded dimethyl 1,3-dithiole-2-thione-4,5-dicarboxylate (O'Connor & Jones, 1970). (3) This latter compound was treated with mercury(II) acetate in acetic acid/chloroform to obtain dimethyl 1,3-dithiole-2-one-4,5-dicarboxylate (Nguyen et al., 2010). (4) In the final step, the 1,3-dithiol-2-one compound was coupled by a trimethyl phosphite induced reaction according to a literature protocol (Nguyen et al., 2010). For this purpose methyl 1,3-dithiol-2-one-4,5-dicarboxylate (3.00 g, 12.8 mmol) was dissolved in trimethyl phosphite (7.94 g, 64.0 mmol) and stirred for 8 h at 100 °C. After cooling, a fine red precipitate had formed which was filtered and washed with a small amount of cold ethanol to yield 1.62 g (58 %) of the substituted TTF. Physical data of the compound correspond to reported values (Yoneda et al., 1978). Suitable dark red single crystals for X-ray diffraction were grown by slow evaporation from a solution of the title compound in chloroform.

Refinement top

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.96 Å, and Uiso=1.5 Ueq (parent atom).

Structure description top

Tetrathiafulvalene derivatives are molecules of high importance relating to electroconductive behaviour (Takase et al., 2011).

The present structure of the title compound (TTF) has been refined to an R-value of 2.06% which is clearly better than 7.1% of the previous study reported in 1976 by Belsky and Voet. In particular, this enabled us to refine the positions of hydrogen atoms of the methyl groups with improved accuracy making it possible to find potential hydrogen bonds. In conformity with previous findings, the TTF scaffold is planar and the methoxycarbonyl functions are slightly twisted out of the ring plane [interplanar angles 25.60 (1) and 42.77 (2)°] (Fig. 1).

The refinement shows the molecules being arranged in a layered structure (Fig. 2) stabilized by C—H···O (Desiraju et al., 1999; Katzsch et al., 2011; Fischer et al., 2011) and C—H···S contacts (Mata et al., 2010; Novoa et al., 1995) (Table 1). Two molecules each are associated forming special dimer type species (Fig. 2). In one case, they involve two ester functions [d(C5—H5A···O1) = 2.50 Å] giving rise to a hydrogen bonded ring motif R22(10) (Bernstein et al., 1995; Petersen et al., 2007). In the other case, adjacent molecules show hydrogen bonding interactions between ester methyl groups and sulfur atoms [d(C7—H7A···S1) = 2.83 Å] (Saad et al., 2010; Lu et al., 2005). The layers are also connected via C—H···O contacts including a methyl group and a carbonyl function [d(C5—H5C···O3) = 2.65 Å] of superimposed molecules.

For the first structure determination of the title compound, see: Belsky & Voet (1976). For a previously reported experimental procedure and physical data, see: Yoneda et al. (1978). For C—H···O hydrogen bonds, see: Desiraju & Steiner (1999); Katzsch et al. (2011); Fischer et al. (2011). For C—H···S hydrogen bonds, see: Mata et al. (2010); Novoa et al. (1995); Lu et al. (2005); Saad et al. (2010). For a description of ring motifs, see: Bernstein et al. (1995); Petersen et al. (2007). For several steps of the synthetic procedure, see: Degani et al. (1986); O'Connor & Jones (1970); Nguyen et al. (2010). For general background to the electroconductive behaviour of tetrathiafulvalene derivatives, see: Takase et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective view of the title compound showing thermal ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Hydrogen-bonds within the layer structure of tetra-substituted TTF.
Tetramethyl tetrathiafulvalene-2,3,6,7-tetracarboxylate top
Crystal data top
C14H12O8S4Z = 1
Mr = 436.48F(000) = 224
Triclinic, P1Dx = 1.668 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8666 (2) ÅCell parameters from 9962 reflections
b = 7.8783 (2) Åθ = 2.5–45.3°
c = 8.4335 (2) ŵ = 0.59 mm1
α = 100.221 (1)°T = 100 K
β = 99.255 (1)°Needle, red
γ = 99.328 (1)°0.64 × 0.16 × 0.15 mm
V = 434.53 (2) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1534 independent reflections
Radiation source: fine-focus sealed tube1471 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
phi and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 78
Tmin = 0.705, Tmax = 0.917k = 99
10884 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)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0273P)2 + 0.222P]
where P = (Fo2 + 2Fc2)/3
1534 reflections(Δ/σ)max = 0.026
120 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C14H12O8S4γ = 99.328 (1)°
Mr = 436.48V = 434.53 (2) Å3
Triclinic, P1Z = 1
a = 6.8666 (2) ÅMo Kα radiation
b = 7.8783 (2) ŵ = 0.59 mm1
c = 8.4335 (2) ÅT = 100 K
α = 100.221 (1)°0.64 × 0.16 × 0.15 mm
β = 99.255 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1534 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
1471 reflections with I > 2σ(I)
Tmin = 0.705, Tmax = 0.917Rint = 0.021
10884 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0210 restraints
wR(F2) = 0.055H-atom parameters constrained
S = 1.08Δρmax = 0.25 e Å3
1534 reflectionsΔρmin = 0.23 e Å3
120 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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
xyzUiso*/Ueq
S10.30978 (5)0.63798 (4)1.10656 (4)0.01479 (11)
S20.06589 (5)0.56717 (4)0.76932 (4)0.01637 (11)
O10.69629 (14)0.93615 (13)0.94082 (12)0.0194 (2)
O20.72198 (13)0.79160 (12)1.14884 (11)0.0167 (2)
O30.27914 (16)0.78034 (15)0.55357 (13)0.0265 (3)
O40.56544 (14)0.69314 (13)0.64417 (11)0.0181 (2)
C10.0779 (2)0.54255 (17)0.97428 (16)0.0140 (3)
C20.4249 (2)0.71176 (17)0.95464 (16)0.0131 (3)
C30.31610 (19)0.67605 (17)0.80137 (16)0.0138 (3)
C40.62881 (19)0.82552 (17)1.00955 (16)0.0138 (3)
C50.9200 (2)0.90095 (19)1.21844 (18)0.0196 (3)
H5A1.00060.89961.13530.029*
H5B0.98400.85601.30750.029*
H5C0.90611.01941.25840.029*
C60.3832 (2)0.72501 (17)0.65299 (16)0.0153 (3)
C70.6552 (2)0.7573 (2)0.51653 (17)0.0226 (3)
H7A0.57900.69460.41080.034*
H7B0.79110.73910.52700.034*
H7C0.65480.88050.52720.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01005 (18)0.02032 (19)0.01379 (18)0.00123 (13)0.00238 (12)0.00683 (13)
S20.01129 (18)0.02217 (19)0.01518 (18)0.00117 (13)0.00129 (13)0.00788 (13)
O10.0162 (5)0.0197 (5)0.0233 (5)0.0007 (4)0.0067 (4)0.0087 (4)
O20.0108 (5)0.0206 (5)0.0168 (5)0.0020 (4)0.0011 (4)0.0055 (4)
O30.0216 (6)0.0423 (7)0.0225 (5)0.0111 (5)0.0064 (4)0.0184 (5)
O40.0158 (5)0.0265 (5)0.0161 (5)0.0054 (4)0.0076 (4)0.0096 (4)
C10.0116 (6)0.0158 (6)0.0147 (6)0.0017 (5)0.0017 (5)0.0049 (5)
C20.0127 (6)0.0131 (6)0.0160 (6)0.0035 (5)0.0064 (5)0.0053 (5)
C30.0109 (6)0.0133 (6)0.0184 (7)0.0019 (5)0.0046 (5)0.0050 (5)
C40.0126 (6)0.0143 (6)0.0157 (6)0.0035 (5)0.0062 (5)0.0022 (5)
C50.0104 (7)0.0216 (7)0.0231 (7)0.0023 (5)0.0002 (5)0.0024 (6)
C60.0154 (7)0.0147 (6)0.0152 (7)0.0009 (5)0.0032 (5)0.0032 (5)
C70.0188 (7)0.0342 (8)0.0176 (7)0.0022 (6)0.0087 (6)0.0110 (6)
Geometric parameters (Å, º) top
S1—C21.7452 (13)C1—C1i1.343 (3)
S1—C11.7570 (13)C2—C31.3419 (19)
S2—C31.7468 (13)C2—C41.4882 (18)
S2—C11.7636 (13)C3—C61.4921 (18)
O1—C41.2022 (16)C5—H5A0.9600
O2—C41.3363 (16)C5—H5B0.9600
O2—C51.4559 (16)C5—H5C0.9600
O3—C61.2007 (17)C7—H7A0.9600
O4—C61.3263 (16)C7—H7B0.9600
O4—C71.4487 (16)C7—H7C0.9600
C2—S1—C194.90 (6)O2—C5—H5A109.5
C3—S2—C194.65 (6)O2—C5—H5B109.5
C4—O2—C5115.25 (10)H5A—C5—H5B109.5
C6—O4—C7115.57 (11)O2—C5—H5C109.5
C1i—C1—S1122.42 (14)H5A—C5—H5C109.5
C1i—C1—S2122.68 (14)H5B—C5—H5C109.5
S1—C1—S2114.90 (7)O3—C6—O4125.74 (12)
C3—C2—C4125.13 (12)O3—C6—C3122.87 (12)
C3—C2—S1117.68 (10)O4—C6—C3111.34 (11)
C4—C2—S1116.86 (10)O4—C7—H7A109.5
C2—C3—C6126.96 (12)O4—C7—H7B109.5
C2—C3—S2117.78 (10)H7A—C7—H7B109.5
C6—C3—S2115.23 (10)O4—C7—H7C109.5
O1—C4—O2125.14 (12)H7A—C7—H7C109.5
O1—C4—C2124.48 (12)H7B—C7—H7C109.5
O2—C4—C2110.33 (11)
C2—S1—C1—C1i178.58 (16)C5—O2—C4—O10.21 (18)
C2—S1—C1—S21.44 (8)C5—O2—C4—C2177.38 (10)
C3—S2—C1—C1i177.53 (16)C3—C2—C4—O122.1 (2)
C3—S2—C1—S12.49 (8)S1—C2—C4—O1151.10 (11)
C1—S1—C2—C30.67 (11)C3—C2—C4—O2160.29 (12)
C1—S1—C2—C4173.05 (10)S1—C2—C4—O226.51 (14)
C4—C2—C3—C67.2 (2)C7—O4—C6—O310.1 (2)
S1—C2—C3—C6179.69 (10)C7—O4—C6—C3172.26 (11)
C4—C2—C3—S2170.52 (10)C2—C3—C6—O3137.60 (15)
S1—C2—C3—S22.63 (15)S2—C3—C6—O340.13 (17)
C1—S2—C3—C23.06 (11)C2—C3—C6—O444.73 (18)
C1—S2—C3—C6178.99 (10)S2—C3—C6—O4137.54 (10)
Symmetry code: (i) x, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···S1ii0.962.833.735 (2)158
C5—H5A···O1iii0.962.503.324 (2)143
C5—H5C···O3iv0.962.653.481 (2)145
Symmetry codes: (ii) x, y, z1; (iii) x+2, y+2, z+2; (iv) x+1, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC14H12O8S4
Mr436.48
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)6.8666 (2), 7.8783 (2), 8.4335 (2)
α, β, γ (°)100.221 (1), 99.255 (1), 99.328 (1)
V3)434.53 (2)
Z1
Radiation typeMo Kα
µ (mm1)0.59
Crystal size (mm)0.64 × 0.16 × 0.15
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.705, 0.917
No. of measured, independent and
observed [I > 2σ(I)] reflections
10884, 1534, 1471
Rint0.021
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.055, 1.08
No. of reflections1534
No. of parameters120
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.23

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7A···S1i0.962.833.735 (2)157.7
C5—H5A···O1ii0.962.503.324 (2)143.3
C5—H5C···O3iii0.962.653.481 (2)144.9
Symmetry codes: (i) x, y, z1; (ii) x+2, y+2, z+2; (iii) x+1, y+2, z+2.
 

Acknowledgements

This work was performed and funded within the Cluster of Excellence "Structure Design of Novel High-Performance Materials via Atomic Design and Defect Engineering (ADDE)" that is financially supported by the European Union (European regional development fund) and by the Ministry of Science and Art of Saxony (SMWK).

References

First citationBelsky, V. K. & Voet, D. (1976). Acta Cryst. B32, 272–274.  CSD CrossRef IUCr Journals Web of Science Google Scholar
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