Bis(cyclo­hexyl­ammonium) tetra­chlorido­diphenyl­stannate(IV)

Sarr, M.; Merkens, C.; Diassé-Sarr, A.; Diop, L.; Englert, U.

doi:10.1107/S160053681401109X

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Pages m220-m221

doi:10.1107/S160053681401109X

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Bis(cyclohexylammonium) tetrachloridodiphenylstannate(IV)

Modou Sarr,^a ^* Carina Merkens,^b Aminata Diassé-Sarr,^a Libasse Diop ^a and Ulli Englert ^b

^aLaboratoire de Chimie Minerale et Analytique, Département de Chimie, Faculté des Sciences et Techniques Université Cheikh Anta Diop, Dakar, Senegal, and ^bInstitut für Anorganische Chemie, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany
^*Correspondence e-mail: modousarr41@gmail.com

(Received 20 April 2014; accepted 14 May 2014; online 17 May 2014)

The title compound, (C₆H₁₄N)₂[Sn(C₆H₅)₂Cl₄], contains cyclohexylammonium cations in general positions and a stannate(IV) anion that is located on a twofold rotation axis. The Sn^IV atom in the complex anion is surrounded by four Cl⁻ ligands and two trans-phenyl groups in a distorted octahedral configuration. The anions are connected with the cations through N—H⋯Cl hydrogen bonds. Every cation is involved in three N—H⋯Cl bonds to the chloride ligands of three different anions, and each chloride ligand is linked to two cations. This arrangement leads to a layered structure parallel to (010).

CCDC reference: 1002989

Related literature

For applications of organotin(IV) compounds, see: Evans & Karpel (1985 ); Kapoor et al. (2005 ). For compounds containing the [Sn(C₆H₅)₂Cl₄]²⁻ anion in a cis or trans-conformation, see: Garcia-Seijo et al. (2001 ); Fernandez et al. (2002 ); Venkatraman et al. (2004 ); Diop et al. (2011 ). For crystal structures of related tin(IV) compounds, see: Sarr et al. (2013a ,b ).

Experimental

Crystal data

(C₆H₁₄N)₂[Sn(C₆H₅)₂Cl₄]
M_r = 615.05
Orthorhombic, F d d 2
a = 13.558 (4) Å
b = 49.646 (14) Å
c = 8.058 (2) Å
V = 5424 (3) Å³
Z = 8
Mo Kα radiation
μ = 1.35 mm⁻¹
T = 100 K
0.30 × 0.21 × 0.05 mm

Data collection

Bruker D8 goniometer with APEX area detector
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.687, T_max = 0.935
15474 measured reflections
2772 independent reflections
2563 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.100
S = 1.06
2772 reflections
151 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.92 e Å⁻³
Δρ_min = −0.67 e Å⁻³
Absolute structure: Flack (1983 ), 1281 Friedel pairs
Absolute structure parameter: 0.23 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl2ⁱ	0.91 (3)	2.35 (4)	3.244 (8)	166 (10)
N1—H1B⋯Cl1ⁱⁱ	0.91 (3)	2.36 (6)	3.172 (9)	148 (8)
N1—H1C⋯Cl2ⁱⁱⁱ	0.90 (3)	2.60 (7)	3.328 (9)	139 (9)
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) -x, -y, z-1; (iii) -x, -y, z.

Data collection: SMART (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL2013.

Supporting information

CCDC reference: 1002989

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681401109X/wm5023sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681401109X/wm5023Isup2.hkl

checkCIF report

Comment top

Our interest for organotin(IV) compounds (Sarr et al., 2013a,b) is related to applications found in various fields like in medicine, industry or agriculture (Evans & Karpel, 1985; Kapoor et al., 2005).

The crystal structure of the title compound, 2(C₆H₁₄N)⁺[Sn(C₆H₅)₂Cl₄]^2-, consists of cyclohexylammonium cations and a [SnPh₂Cl₄]^2- anion that is located on a twofold rotation axis. The Sn^IV atom is bonded to two trans-phenyl groups and four chloride ligands in a distorted octahedral geometry (Fig. 1). For reasons of symmetry, the Sn—C bond lengths are equal and amount to 2.142 (5) Å. The two independent Sn—Cl bond lengths have very similar values [2.5685 (16) and 2.5842 (17) Å] and may be compared to the values of 2.5722 (6) and 2.5796 (6) Å reported for bis(trimethylammonium) tetrachloridodiphenylstannate(IV) (Diop et al., 2011). The C—Sn—C angle (179.6 (4) °) is linear within experimental error. The angles in the equatorial plane of the pseudo-octahedron deviate slightly from 90° [Cl1—Sn1—Cl1ⁱ = 91.12 (8)°; Cl1—Sn1—Cl2 = 89.41 (5)°, i = -x, -y, z]. The tetrachloridodiphenylstannate(IV anion, [SnPh₂Cl₄]^2-, in its cis or trans configurations has been reported previously by several authors with different counter cations (Garcia-Seijo et al., 2001; Fernandez et al., 2002; Venkatraman et al., 2004; Diop et al., 2011).

Each cation in the title compound is linked to Cl atoms of three different anions through classical N—H···Cl hydrogen bonds (Fig. 2, Table 1), leading to a layered arrangement parallel to (010).

Related literature top

For applications of organotin(IV) compounds, see: Evans & Karpel (1985); Kapoor et al. (2005). For compounds containing the [Sn(C₆H₅)₂Cl₄]^2- anion in a cis or trans-conformation, see: Garcia-Seijo et al. (2001); Fernandez et al. (2002); Venkatraman et al. (2004); Diop et al. (2011). For crystal structures of related tin(IV) compounds, see: Sarr et al. (2013a,b)

Experimental top

Equimolar amounts of cyclohexylamin and oxalic were dissolved in water; crystals formed by slow evaporation. Their elemental analyses, calculated/ % (found/ %), C: 53.31 (53.05); %H: 9.91(10.28); %N: 8.88(8.40), suggest the composition (CyNH₃)₂(C₂O₄)^.3/2H₂O. Crystals suitable for the X-ray determination of the title compound were obtained by mixing methanolic solutions of (CyNH₃)₂(C₂O₄)^.3/2H₂O and SnPh₂Cl₂ in a 1:1 ratio and subsequent slow solvent evaporation.

Computing details top

Data collection: SMART (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular entities of the title compound with partial atom labelling. [Symmetry code: (i) -x, -y, z.]
	Fig. 2. A view of N—H···Cl hydrogen bonds in the crystal structure of the title compound. H atoms non-participating in hydrogen bonding and the phenyl groups have been omitted for clarity.

Bis(cyclohexylammonium) tetrachloridodiphenylstannate(IV) top

Crystal data top

(C₆H₁₄N)₂[Sn(C₆H₅)₂Cl₄]	F(000) = 2512
M_r = 615.05	D_x = 1.506 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 5810 reflections
a = 13.558 (4) Å	θ = 3.0–26.2°
b = 49.646 (14) Å	µ = 1.35 mm⁻¹
c = 8.058 (2) Å	T = 100 K
V = 5424 (3) Å³	Plate, colorless
Z = 8	0.30 × 0.21 × 0.05 mm

Data collection top

Bruker D8 goniometer with APEX area detector diffractometer	2772 independent reflections
Radiation source: Incoatec microsource	2563 reflections with I > 2σ(I)
Multilayer optics monochromator	R_int = 0.069
ω scans	θ_max = 26.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.687, T_max = 0.935	k = −62→62
15474 measured reflections	l = −10→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.020P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.004
2772 reflections	Δρ_max = 1.92 e Å⁻³
151 parameters	Δρ_min = −0.67 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 1281 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.23 (5)

Crystal data top

(C₆H₁₄N)₂[Sn(C₆H₅)₂Cl₄]	V = 5424 (3) Å³
M_r = 615.05	Z = 8
Orthorhombic, Fdd2	Mo Kα radiation
a = 13.558 (4) Å	µ = 1.35 mm⁻¹
b = 49.646 (14) Å	T = 100 K
c = 8.058 (2) Å	0.30 × 0.21 × 0.05 mm

Data collection top

Bruker D8 goniometer with APEX area detector diffractometer	2772 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2563 reflections with I > 2σ(I)
T_min = 0.687, T_max = 0.935	R_int = 0.069
15474 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	Δρ_max = 1.92 e Å⁻³
S = 1.06	Δρ_min = −0.67 e Å⁻³
2772 reflections	Absolute structure: Flack (1983), 1281 Friedel pairs
151 parameters	Absolute structure parameter: 0.23 (5)
4 restraints

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
Sn1	−0.0000	−0.0000	0.72474 (9)	0.02578 (15)
Cl1	−0.11741 (11)	0.01834 (3)	0.94793 (18)	0.0329 (4)
Cl2	−0.11954 (10)	0.01707 (3)	0.4982 (2)	0.0308 (4)
C1	0.0727 (4)	0.03830 (10)	0.7238 (8)	0.0285 (11)
C2	0.0212 (3)	0.06170 (10)	0.7321 (11)	0.0277 (12)
H2	−0.0484	0.0609	0.7439	0.033*
C3	0.0659 (4)	0.08670 (11)	0.7241 (9)	0.0362 (13)
H3	0.0275	0.1027	0.7226	0.043*
C4	0.1690 (4)	0.08788 (11)	0.7183 (9)	0.0357 (13)
H4	0.2016	0.1048	0.7182	0.043*
C5	0.2215 (5)	0.06497 (13)	0.7128 (10)	0.0372 (14)
H5	0.2914	0.0659	0.7060	0.045*
C6	0.1752 (4)	0.03965 (11)	0.7170 (9)	0.0297 (12)
H6	0.2134	0.0236	0.7152	0.036*
N1	0.1784 (4)	0.02720 (11)	0.2043 (9)	0.0375 (13)
H1A	0.233 (4)	0.0271 (15)	0.138 (8)	0.056*
H1B	0.142 (5)	0.0132 (10)	0.164 (8)	0.056*
H1C	0.181 (6)	0.0222 (15)	0.311 (4)	0.056*
C7	0.1431 (4)	0.05466 (11)	0.1699 (7)	0.0317 (14)
H7	0.1271	0.0557	0.0490	0.038*
C8	0.0488 (4)	0.06018 (12)	0.2660 (7)	0.0326 (15)
H8A	−0.0029	0.0472	0.2316	0.039*
H8B	0.0610	0.0577	0.3862	0.039*
C9	0.0141 (4)	0.08851 (11)	0.2336 (16)	0.0401 (14)
H9A	−0.0452	0.0921	0.3018	0.048*
H9B	−0.0050	0.0902	0.1155	0.048*
C10	0.0917 (5)	0.10933 (13)	0.2730 (9)	0.0489 (19)
H10A	0.1054	0.1093	0.3937	0.059*
H10B	0.0674	0.1274	0.2419	0.059*
C11	0.1854 (5)	0.10318 (12)	0.1787 (8)	0.0417 (17)
H11A	0.1735	0.1060	0.0588	0.050*
H11B	0.2374	0.1160	0.2138	0.050*
C12	0.2216 (5)	0.07509 (12)	0.2055 (10)	0.0343 (14)
H12A	0.2438	0.0731	0.3219	0.041*
H12B	0.2790	0.0717	0.1325	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.0195 (2)	0.0327 (3)	0.0251 (2)	−0.0025 (2)	−0.000	−0.000
Cl1	0.0289 (7)	0.0418 (8)	0.0281 (11)	−0.0032 (6)	0.0082 (7)	−0.0044 (7)
Cl2	0.0236 (6)	0.0372 (7)	0.0316 (11)	−0.0016 (5)	−0.0062 (7)	0.0032 (7)
C1	0.040 (3)	0.031 (3)	0.014 (2)	−0.002 (2)	−0.006 (3)	0.001 (3)
C2	0.020 (3)	0.042 (3)	0.021 (3)	0.000 (2)	0.009 (4)	−0.002 (3)
C3	0.048 (4)	0.033 (3)	0.028 (3)	0.002 (2)	0.002 (4)	−0.006 (3)
C4	0.045 (3)	0.037 (3)	0.025 (3)	−0.013 (3)	−0.006 (3)	−0.002 (3)
C5	0.037 (3)	0.047 (4)	0.028 (3)	−0.012 (3)	0.001 (3)	−0.007 (4)
C6	0.025 (3)	0.041 (3)	0.023 (3)	−0.001 (2)	0.010 (3)	−0.002 (3)
N1	0.030 (3)	0.035 (3)	0.047 (4)	0.002 (2)	0.005 (3)	−0.003 (3)
C7	0.031 (3)	0.031 (3)	0.032 (3)	−0.001 (3)	0.003 (2)	−0.000 (2)
C8	0.028 (3)	0.043 (4)	0.027 (4)	−0.004 (3)	−0.001 (2)	0.001 (2)
C9	0.027 (3)	0.041 (3)	0.052 (4)	0.008 (3)	−0.002 (4)	−0.009 (5)
C10	0.060 (4)	0.032 (3)	0.056 (5)	0.005 (3)	0.003 (3)	−0.002 (3)
C11	0.047 (4)	0.037 (4)	0.041 (4)	−0.010 (3)	−0.000 (3)	−0.001 (3)
C12	0.036 (3)	0.041 (3)	0.026 (4)	−0.011 (3)	0.005 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Sn1—C1ⁱ	2.142 (5)	N1—H1B	0.91 (2)
Sn1—C1	2.142 (5)	N1—H1C	0.90 (2)
Sn1—Cl1	2.5685 (16)	C7—C12	1.498 (8)
Sn1—Cl1ⁱ	2.5686 (16)	C7—C8	1.519 (8)
Sn1—Cl2	2.5842 (17)	C7—H7	1.0000
Sn1—Cl2ⁱ	2.5843 (17)	C8—C9	1.506 (8)
C1—C2	1.357 (7)	C8—H8A	0.9900
C1—C6	1.392 (7)	C8—H8B	0.9900
C2—C3	1.383 (7)	C9—C10	1.509 (9)
C2—H2	0.9500	C9—H9A	0.9900
C3—C4	1.399 (8)	C9—H9B	0.9900
C3—H3	0.9500	C10—C11	1.511 (9)
C4—C5	1.343 (9)	C10—H10A	0.9900
C4—H4	0.9500	C10—H10B	0.9900
C5—C6	1.406 (8)	C11—C12	1.494 (9)
C5—H5	0.9500	C11—H11A	0.9900
C6—H6	0.9500	C11—H11B	0.9900
N1—C7	1.471 (8)	C12—H12A	0.9900
N1—H1A	0.91 (2)	C12—H12B	0.9900

C1ⁱ—Sn1—C1	179.6 (4)	H1B—N1—H1C	99 (7)
C1ⁱ—Sn1—Cl1	91.82 (16)	N1—C7—C12	111.1 (5)
C1—Sn1—Cl1	88.46 (17)	N1—C7—C8	110.2 (5)
C1ⁱ—Sn1—Cl1ⁱ	88.45 (17)	C12—C7—C8	112.2 (5)
C1—Sn1—Cl1ⁱ	91.82 (16)	N1—C7—H7	107.7
Cl1—Sn1—Cl1ⁱ	91.12 (8)	C12—C7—H7	107.7
C1ⁱ—Sn1—Cl2	90.00 (17)	C8—C7—H7	107.7
C1—Sn1—Cl2	89.72 (16)	C9—C8—C7	110.1 (6)
Cl1—Sn1—Cl2	89.41 (5)	C9—C8—H8A	109.6
Cl1ⁱ—Sn1—Cl2	178.38 (5)	C7—C8—H8A	109.6
C1ⁱ—Sn1—Cl2ⁱ	89.72 (16)	C9—C8—H8B	109.6
C1—Sn1—Cl2ⁱ	90.00 (17)	C7—C8—H8B	109.6
Cl1—Sn1—Cl2ⁱ	178.39 (5)	H8A—C8—H8B	108.2
Cl1ⁱ—Sn1—Cl2ⁱ	89.41 (5)	C8—C9—C10	112.6 (6)
Cl2—Sn1—Cl2ⁱ	90.10 (8)	C8—C9—H9A	109.1
C2—C1—C6	118.3 (5)	C10—C9—H9A	109.1
C2—C1—Sn1	121.5 (4)	C8—C9—H9B	109.1
C6—C1—Sn1	120.1 (4)	C10—C9—H9B	109.1
C1—C2—C3	122.7 (5)	H9A—C9—H9B	107.8
C1—C2—H2	118.6	C9—C10—C11	110.0 (6)
C3—C2—H2	118.6	C9—C10—H10A	109.7
C2—C3—C4	118.5 (5)	C11—C10—H10A	109.7
C2—C3—H3	120.8	C9—C10—H10B	109.7
C4—C3—H3	120.8	C11—C10—H10B	109.7
C5—C4—C3	119.7 (5)	H10A—C10—H10B	108.2
C5—C4—H4	120.2	C12—C11—C10	113.1 (5)
C3—C4—H4	120.2	C12—C11—H11A	109.0
C4—C5—C6	121.3 (6)	C10—C11—H11A	109.0
C4—C5—H5	119.3	C12—C11—H11B	109.0
C6—C5—H5	119.3	C10—C11—H11B	109.0
C1—C6—C5	119.3 (5)	H11A—C11—H11B	107.8
C1—C6—H6	120.3	C11—C12—C7	111.8 (5)
C5—C6—H6	120.3	C11—C12—H12A	109.3
C7—N1—H1A	99 (5)	C7—C12—H12A	109.3
C7—N1—H1B	118 (5)	C11—C12—H12B	109.3
H1A—N1—H1B	103 (6)	C7—C12—H12B	109.3
C7—N1—H1C	117 (5)	H12A—C12—H12B	107.9
H1A—N1—H1C	122 (7)

C1ⁱ—Sn1—C1—C2	93.3 (8)	C2—C3—C4—C5	3.1 (11)
Cl1—Sn1—C1—C2	−41.0 (6)	C3—C4—C5—C6	−1.6 (12)
Cl1ⁱ—Sn1—C1—C2	−132.1 (6)	C2—C1—C6—C5	−2.3 (10)
Cl2—Sn1—C1—C2	48.4 (6)	Sn1—C1—C6—C5	178.6 (6)
Cl2ⁱ—Sn1—C1—C2	138.5 (6)	C4—C5—C6—C1	1.2 (11)
C1ⁱ—Sn1—C1—C6	−87.6 (4)	N1—C7—C8—C9	178.7 (6)
Cl1—Sn1—C1—C6	138.0 (5)	C12—C7—C8—C9	54.3 (7)
Cl1ⁱ—Sn1—C1—C6	47.0 (5)	C7—C8—C9—C10	−55.7 (10)
Cl2—Sn1—C1—C6	−132.5 (5)	C8—C9—C10—C11	55.1 (10)
Cl2ⁱ—Sn1—C1—C6	−42.4 (5)	C9—C10—C11—C12	−53.5 (8)
C6—C1—C2—C3	4.0 (12)	C10—C11—C12—C7	53.4 (8)
Sn1—C1—C2—C3	−177.0 (6)	N1—C7—C12—C11	−177.3 (6)
C1—C2—C3—C4	−4.4 (12)	C8—C7—C12—C11	−53.5 (7)

Symmetry code: (i) −x, −y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2ⁱⁱ	0.91 (3)	2.35 (4)	3.244 (8)	166 (10)
N1—H1B···Cl1ⁱⁱⁱ	0.91 (3)	2.36 (6)	3.172 (9)	148 (8)
N1—H1C···Cl2ⁱ	0.90 (3)	2.60 (7)	3.328 (9)	139 (9)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2ⁱ	0.91 (3)	2.35 (4)	3.244 (8)	166 (10)
N1—H1B···Cl1ⁱⁱ	0.91 (3)	2.36 (6)	3.172 (9)	148 (8)
N1—H1C···Cl2ⁱⁱⁱ	0.90 (3)	2.60 (7)	3.328 (9)	139 (9)

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

References

Bruker (2009). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconson, USA. Google Scholar
Diop, T., Diop, L., Molloy, K. C. K. & Kocioc-Köhn, G. (2011). Acta Cryst. E67, m203–m204. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Evans, C. J. & Karpel, S. (1985). Organotin Compounds in Modern Technology. J. Organomet. Chem. Library, Vol. 16. Amsterdam: Elsevier. Google Scholar
Fernandez, D., Garcia-Seijo, M. I., Kegl, T., Petocz, G., Kollar, L. & Garcia-Fermandez, M. E. (2002). Inorg. Chem. 41, 4435–4443. Web of Science PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Garcia-Seijo, M. I., Castineiras, A., Mahieu, B., Janosi, J., Berente, Z., Kollar, L. & Fernandez, G. (2001). Polyhedron, 20, 855–868. CAS Google Scholar
Kapoor, R. N., Guillory, P., Schulte, L., Cervantes-Lee, F., Haiduc, I., Parkanyi, L. & Pannell, K. H. (2005). Appl. Organomet. Chem. 19, 510–517. Web of Science CSD CrossRef CAS Google Scholar
Sarr, M., Diasse-Sarr, A., Diallo, W., Plasseraud, L. & Cattey, H. (2013a). Acta Cryst. E69, m473–m474. CSD CrossRef CAS IUCr Journals Google Scholar
Sarr, M., Diallo, W., Diasse-Sarr, A., Plasseraud, L. & Cattey, H. (2013b). Acta Cryst. E69, m581–m582. CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Venkatraman, R., Ray, P. C. & Fronczek, F. R. (2004). Acta Cryst. E60, m1035–m1037. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 6| June 2014| Pages m220-m221

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