Dichloridobis{2-[(dimethyl­amino)­meth­yl]phen­yl}bis­{2-[(dimethyl­aza­nium­yl)meth­yl]phen­yl}di-μ-hydroxido-di-μ3-oxido-tetra­phenyl­tetra­tin(IV) dichloride deuterochloro­form deca­solvate

Turek, J.; Padělková, Z.

doi:10.1107/S1600536811048872

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1890-m1891

https://doi.org/10.1107/S1600536811048872

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Dichloridobis{2-[(dimethylamino)methyl]phenyl}bis{2-[(dimethylazaniumyl)methyl]phenyl}di-μ-hydroxido-di-μ₃-oxido-tetraphenyltetratin(IV) dichloride deuterochloroform decasolvate

Jan Turek ^a and Zdeňka Padělková ^a ^*

^aDepartment of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 53210 Pardubice, Czech Republic
^*Correspondence e-mail: zdenka.padelkova@upce.cz

(Received 9 August 2011; accepted 16 November 2011; online 30 November 2011)

The ladder-like structure of the tetranuclear title compound, [Sn₄(C₆H₅)₄Cl₂O₂(OH)₂(C₉H₁₃N)₂(C₉H₁₂N)₂]Cl₂·10CDCl₃, consists of two five- and two six-coordinated Sn^IV atoms bridged by oxide or hydroxide groups. The chelating ligands reveal rather strong Sn—N bonds [2.517 (4) Å], but the protonated dimethylamino groups in the periphery of the complex show no interaction with the metal atoms. The complex cation is located on an inversion centre. The chloride anion is linked to the complex molecule by strong intramolecular O—H⋯Cl and N—H⋯Cl hydrogen bonds. Five independent deuterochloroform accompany the complex, two of them are disordered [occupancy ratios 0.63 (2):0.27 (2) and 0.60 (2):0.40 (2)].

Related literature

For related structures, see: Novák et al. (2006 , 2007 ); Varga & Silvestru (2007 ); Thoonen et al. (2006 ); Jambor et al. (2001 ); Padělková et al. (2007 ). For similar tetranuclear aggregates, see: Beckmann et al. (2001 ); Cox & Tiekink (1994 ); Kresinski et al. (1994 ); Lo & Ng (2009 ); Mohamed et al. (2004 ); Puff et al. (1983 ); Tiekink (1991 ); Vollano et al. (1984 ); Zhang et al. (2009 ). For similar hydrogen bonding in C,N-chelated organotin compounds, see: Padělková et al. (2009 ); Švec et al. (2010 , 2011 ).

Experimental

Crystal data

[Sn₄(C₆H₅)₄Cl₂O₂(OH)₂(C₉H₁₃N)₂(C₉H₁₂N)₂]Cl₂·10CDCl₃
M_r = 2733.56
Triclinic, $[P \overline 1]$
a = 11.9279 (5) Å
b = 15.4080 (12) Å
c = 15.9651 (14) Å
α = 83.752 (7)°
β = 68.178 (4)°
γ = 76.339 (5)°
V = 2646.1 (3) Å³
Z = 1
Mo Kα radiation
μ = 1.84 mm⁻¹
T = 150 K
0.28 × 0.26 × 0.21 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer
Absorption correction: gaussian (Coppens, 1970 ) T_min = 0.758, T_max = 0.820
51386 measured reflections
12052 independent reflections
9459 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.146
S = 1.08
12052 reflections
598 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 1.95 e Å⁻³
Δρ_min = −1.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯Cl2	0.93	2.21	3.079 (4)	156.0
N1—H1⋯Cl2	0.91	2.30	3.106 (5)	147.6

Data collection: COLLECT (Hooft, 1998 ) and DENZO (Otwinowski & Minor, 1997 ); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811048872/aa2022sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048872/aa2022Isup2.hkl

checkCIF report

Comment top

The common feature of the interaction of C,N-chelated organotin(IV) compounds with protic acids, as well as the mono- and diorganotin compounds, which have the most Lewis acidic tin atom centre, is the hydrolysis. A plethora of such hydrolytic products was identified in the past, including a number of molecular structures determined by X-ray diffraction techniques. The molecular structure of the title compound (Fig. 1) consists of a tetranuclear, nearly planar, aggregate of two central L^CNPhSnO units and two peripherical L^CNPhSn(OH)Cl units (L^CN = 2-(Me₂NCH₂)C₆H₄-). Similar tetranuclear aggregates were found earlier, for example for octabenzyl- (Mohamed et al., 2004), octaisopropyl- (Puff et al., 1983), octa(trimethylsilylmethyl)- (Puff et al., 1983), octaphenyl- (Vollano et al., 1984), octa(2-chlorobenzyl)- (Zhang et al., 2009) , octa(4-chlorobenzyl)- (Lo & Ng, 2009) octaphenyl (Kresinski et al, 1994; Cox & Tiekink, 1994; Tiekink, 1991) and tetra(trimethylsilylmethyl)-tetra-t-butyl- (Beckmann et al., 2001) derivative, respectively. The major difference between I and the rest of compounds is that all these compounds have all the tin atoms five coordinated. In I, the chelating dimethylaminomethyl arms of outer units are protonated by HCl. The chlorine anion is being out of the primary tin coordination sphere but is strongly connected by hydrogen bridges to both OH and NH groups (3.079 (4) Å, 3.106 (5) Å; Fig. 2). These hydrogen bonds are typical for C,N-chelated organotin compounds, as for example for L^CN(n-Bu)₂SnCl.HCl (Švec et al., 2010) or [L^CN(n-Bu)SnOC(O)CF₃]₂(µ-OH)₂ (Švec et al., 2011), but the presence of both types of hydrogen bonds in the same molecule were not observed before. The inner tin atoms coordination polyhedra are of very deformed trigonal bipyramids with both carbon atoms of the ligand and phenyl substituent and the bridging oxygen atom in equatorial positions, despite of that the value of the sum of interatomic angles in equatorial girdle is rather low (323.7°). The axial positions of these tin atoms are filled with the bridging OH group and the second bridging oxygen atom, where Sn1–O2 distances are a bit longer than in cases of the equatorial ones. The equatorial angle is shorter than ideally 180° being only 150.66 (13)°. The outer tin atoms have the C,C-transoidal coordination geometry of strongly deformed octahedron with mutually cis-coordinated O and OH groups, and chlorine and strongly interacting amino nitrogen (Sn–N 2.517 (4) Å) atoms, respectively. The C16–Sn2–C25 angle is wider (158.41 (19)°) than similar angles found in related ladder-like structures (~ 125°, for references see above). The solvent molecules (deuterochloroform) interact with the chloride anions.

Related literature top

For related structures, see: Novák et al. (2006, 2007); Varga et al. (2007); Thoonen et al. (2006); Jambor et al. (2001); Padělková et al. (2007). For similar tetranuclear aggregates, see: Beckmann et al. (2001); Cox & Tiekink (1994); Kresinski et al. (1994); Lo & Ng (2009); Mohamed et al. (2004); Puff et al. (1983); Tiekink (1991); Vollano et al. (1984); Zhang et al. (2009). For similar hydrogen-bonding schemes in C,N-chelated organotin compounds, see: Padělková et al. (2009); Švec et al. (2010, 2011).

Experimental top

The title compound (I, Scheme 1) has been obtained from the reaction mixture of ethylacetoacetate, cyclohexanol and [L^CNPhSn(Cl)]₂O (L^CN = 2-(Me₂NCH₂)C₆H₄-) (1 mol %) in deuterochloroform used as a catalyst in this transesterfication reaction (Padělková et al., 2009) by slow evaporation on the air.

Structure description top

Computing details top

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); data reduction: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title compound with the displacement ellipsoids shown on 50% probability level. Most H atoms are omitted for clarity, H atoms involved in hydrogen bonding are shown. Symmetry code: (a) ?x + 2, ?y + 2, ?z.
	Fig. 2. View of the I structure with the hydrogen bonding along the a axis.

bis{2-[2-(dimethylazaniumyl)methyl]phenyl}-2κC¹,3κC¹- bis{2-[(dimethylamino)methyl]phenyl}-1κC¹,4κC¹- dichlorido-1κCl,4κCl- di-µ-hydroxido-1:2κ²O:O;3:4κ²O:O- di-µ₃-oxido-1:2:3κ³O:O:O;2:3:4κ³O: O:O-tetraphenyl- 1κC¹,2κC¹,3κC¹,4κC¹-tetratin(IV) dichloride deuterochloroform decasolvate top

Crystal data top

[Sn₄(C₆H₅)₄Cl₂O₂(OH)₂(C₉H₁₃N)₂(C₉H₁₂N)₂]Cl₂·10CDCl₃	Z = 1
M_r = 2733.56	F(000) = 1340
Triclinic, P1	D_x = 1.715 Mg m⁻³
Hall symbol: -P 1	Melting point: 395(2) K
a = 11.9279 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.4080 (12) Å	Cell parameters from 51386 reflections
c = 15.9651 (14) Å	θ = 1–27.5°
α = 83.752 (7)°	µ = 1.84 mm⁻¹
β = 68.178 (4)°	T = 150 K
γ = 76.339 (5)°	Block, colourless
V = 2646.1 (3) Å³	0.28 × 0.26 × 0.21 mm

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	12052 independent reflections
Radiation source: fine-focus sealed tube	9459 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
φ and ω scans to fill the Ewald sphere	h = −14→15
Absorption correction: gaussian (Coppens, 1970)	k = −19→20
T_min = 0.758, T_max = 0.820	l = 0→20
51386 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0647P)² + 12.7718P] where P = (F_o² + 2F_c²)/3
12052 reflections	(Δ/σ)_max = 0.001
598 parameters	Δρ_max = 1.95 e Å⁻³
12 restraints	Δρ_min = −1.15 e Å⁻³

Crystal data top

[Sn₄(C₆H₅)₄Cl₂O₂(OH)₂(C₉H₁₃N)₂(C₉H₁₂N)₂]Cl₂·10CDCl₃	γ = 76.339 (5)°
M_r = 2733.56	V = 2646.1 (3) Å³
Triclinic, P1	Z = 1
a = 11.9279 (5) Å	Mo Kα radiation
b = 15.4080 (12) Å	µ = 1.84 mm⁻¹
c = 15.9651 (14) Å	T = 150 K
α = 83.752 (7)°	0.28 × 0.26 × 0.21 mm
β = 68.178 (4)°

Data collection top

Bruker–Nonius KappaCCD area-detector diffractometer	12052 independent reflections
Absorption correction: gaussian (Coppens, 1970)	9459 reflections with I > 2σ(I)
T_min = 0.758, T_max = 0.820	R_int = 0.065
51386 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	12 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0647P)² + 12.7718P] where P = (F_o² + 2F_c²)/3
12052 reflections	Δρ_max = 1.95 e Å⁻³
598 parameters	Δρ_min = −1.15 e Å⁻³

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 > 2sigma(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	Occ. (<1)
Sn1	0.95841 (3)	0.92734 (2)	0.08172 (2)	0.01807 (9)
Sn2	1.05036 (3)	0.81140 (2)	−0.10648 (2)	0.01954 (9)
Cl2	0.90846 (13)	0.65544 (9)	0.18634 (10)	0.0339 (3)
Cl1	1.09431 (12)	0.89042 (9)	−0.26447 (8)	0.0299 (3)
O2	0.9965 (3)	0.7941 (2)	0.0363 (2)	0.0231 (7)
H2	0.9909	0.7414	0.0705	0.035*
O1	0.9676 (3)	1.0635 (2)	0.0551 (2)	0.0197 (7)
C17	0.8196 (5)	0.7435 (3)	−0.0818 (4)	0.0262 (11)
N1	0.8708 (5)	0.7981 (3)	0.3231 (3)	0.0329 (10)
H1	0.8901	0.7755	0.2679	0.039*
N2	1.0295 (4)	0.6531 (3)	−0.1091 (3)	0.0262 (9)
C6	1.2090 (5)	0.8765 (3)	0.0998 (4)	0.0257 (11)
H6	1.2325	0.8850	0.0376	0.031*
C21	0.7933 (5)	0.9018 (4)	−0.1142 (4)	0.0305 (12)
H21	0.8256	0.9531	−0.1293	0.037*
C24	1.1034 (5)	0.5831 (4)	−0.0692 (4)	0.0317 (12)
H24A	1.1897	0.5821	−0.1010	0.048*
H24B	1.0868	0.5262	−0.0735	0.048*
H24C	1.0821	0.5956	−0.0068	0.048*
C1	1.0852 (5)	0.8880 (3)	0.1516 (4)	0.0230 (10)
C25	1.2430 (4)	0.7559 (3)	−0.1350 (4)	0.0232 (10)
C10	0.7635 (4)	0.9427 (3)	0.1424 (3)	0.0238 (10)
C16	0.8670 (5)	0.8216 (3)	−0.1023 (4)	0.0246 (10)
C2	1.0492 (5)	0.8764 (4)	0.2462 (4)	0.0267 (11)
C30	1.2839 (5)	0.7242 (4)	−0.0643 (4)	0.0285 (11)
H30	1.2272	0.7265	−0.0055	0.034*
C3	1.1427 (5)	0.8541 (4)	0.2844 (4)	0.0325 (12)
H3	1.1204	0.8475	0.3467	0.039*
C27	1.4542 (5)	0.7151 (4)	−0.2384 (4)	0.0353 (13)
H27	1.5114	0.7126	−0.2971	0.042*
C5	1.2996 (5)	0.8526 (4)	0.1379 (4)	0.0331 (12)
H5	1.3828	0.8437	0.1016	0.040*
C29	1.4068 (5)	0.6895 (4)	−0.0799 (4)	0.0337 (12)
H29	1.4329	0.6692	−0.0318	0.040*
C22	0.8976 (5)	0.6565 (4)	−0.0624 (4)	0.0289 (11)
H22A	0.8800	0.6498	0.0021	0.035*
H22B	0.8757	0.6071	−0.0812	0.035*
C26	1.3293 (5)	0.7499 (4)	−0.2228 (4)	0.0318 (12)
H26	1.3035	0.7693	−0.2712	0.038*
C15	0.7063 (5)	0.8753 (4)	0.1408 (4)	0.0316 (12)
H15	0.7531	0.8228	0.1111	0.038*
C7	0.9177 (5)	0.8830 (4)	0.3073 (4)	0.0314 (12)
H7A	0.8659	0.9279	0.2823	0.038*
H7B	0.9081	0.9039	0.3652	0.038*
C18	0.6992 (5)	0.7496 (4)	−0.0742 (4)	0.0340 (13)
H18	0.6671	0.6983	−0.0615	0.041*
C23	1.0672 (6)	0.6345 (4)	−0.2063 (4)	0.0354 (13)
H23A	1.1539	0.6329	−0.2359	0.053*
H23B	1.0214	0.6808	−0.2336	0.053*
H23C	1.0505	0.5779	−0.2122	0.053*
C4	1.2641 (6)	0.8420 (4)	0.2317 (4)	0.0352 (13)
H4	1.3239	0.8267	0.2580	0.042*
C28	1.4927 (5)	0.6847 (4)	−0.1682 (5)	0.0374 (14)
H28	1.5759	0.6609	−0.1789	0.045*
C19	0.6255 (5)	0.8298 (4)	−0.0850 (5)	0.0388 (14)
H19	0.5444	0.8326	−0.0798	0.047*
C20	0.6726 (6)	0.9066 (4)	−0.1038 (5)	0.0397 (14)
H20	0.6224	0.9615	−0.1093	0.048*
C14	0.5783 (5)	0.8856 (4)	0.1835 (4)	0.0352 (13)
H14	0.5403	0.8397	0.1824	0.042*
C11	0.6917 (5)	1.0208 (4)	0.1856 (4)	0.0354 (14)
H11	0.7292	1.0671	0.1863	0.042*
C13	0.5093 (5)	0.9624 (4)	0.2265 (5)	0.0415 (15)
H13	0.4244	0.9686	0.2551	0.050*
C9	0.7376 (6)	0.8137 (5)	0.3664 (5)	0.0482 (17)
H9A	0.6998	0.8582	0.3325	0.072*
H9B	0.7140	0.8340	0.4266	0.072*
H9C	0.7108	0.7591	0.3689	0.072*
C12	0.5639 (6)	1.0314 (4)	0.2281 (6)	0.0514 (19)
H12	0.5163	1.0841	0.2570	0.062*
C8	0.9315 (7)	0.7289 (5)	0.3745 (5)	0.0475 (17)
H8A	1.0196	0.7192	0.3448	0.071*
H8B	0.9051	0.6741	0.3771	0.071*
H8C	0.9089	0.7489	0.4346	0.071*
C50	1.2065 (7)	0.5493 (5)	0.1665 (7)	0.058 (2)
D50	1.1290	0.5764	0.1569	0.070*
Cl51	1.3126 (2)	0.50334 (13)	0.06538 (15)	0.0599 (5)
Cl52	1.1760 (2)	0.46445 (16)	0.25107 (16)	0.0680 (6)
Cl53	1.2564 (3)	0.6331 (2)	0.1980 (3)	0.1126 (13)
C60	0.3786 (6)	0.4030 (5)	0.7682 (5)	0.0476 (16)
D60	0.2932	0.4094	0.7718	0.057*
Cl61	0.3904 (2)	0.35616 (16)	0.87085 (14)	0.0653 (5)
Cl62	0.4761 (2)	0.33095 (14)	0.68003 (14)	0.0679 (6)
Cl63	0.4152 (2)	0.50854 (13)	0.74811 (19)	0.0746 (7)
C70A	1.141 (4)	0.165 (3)	0.361 (3)	0.089 (13)	0.37 (2)
D70A	1.1293	0.1533	0.3064	0.107*	0.37 (2)
Cl75	0.992 (2)	0.2562 (10)	0.4102 (13)	0.093 (5)	0.37 (2)
Cl74	1.217 (2)	0.2208 (11)	0.3248 (8)	0.107 (5)	0.37 (2)
Cl76	1.1541 (16)	0.0616 (7)	0.4047 (10)	0.094 (4)	0.37 (2)
C70	1.0976 (12)	0.1618 (10)	0.3631 (8)	0.038 (3)	0.63 (2)
D70	1.0899	0.1513	0.3063	0.045*	0.63 (2)
Cl71	0.9801 (12)	0.2362 (10)	0.4232 (8)	0.141 (5)	0.63 (2)
Cl72	1.2500 (6)	0.1749 (11)	0.3461 (8)	0.137 (5)	0.63 (2)
Cl73	1.0761 (16)	0.0688 (5)	0.4391 (7)	0.119 (4)	0.63 (2)
C80	0.670 (3)	0.167 (2)	0.4596 (17)	0.049 (8)	0.40 (2)
D80	0.7492	0.1555	0.4089	0.059*	0.40 (2)
Cl81	0.619 (2)	0.2718 (12)	0.4575 (9)	0.108 (5)	0.40 (2)
Cl82	0.7067 (8)	0.1475 (7)	0.5587 (5)	0.066 (3)	0.40 (2)
Cl83	0.5908 (14)	0.0680 (14)	0.4646 (18)	0.133 (7)	0.40 (2)
C80A	0.652 (3)	0.1390 (16)	0.4638 (19)	0.064 (7)	0.60 (2)
D80A	0.7375	0.1329	0.4210	0.077*	0.60 (2)
Cl84	0.5572 (11)	0.2548 (6)	0.4667 (4)	0.095 (3)	0.60 (2)
Cl86	0.6429 (19)	0.1145 (11)	0.5677 (6)	0.159 (7)	0.60 (2)
Cl85	0.5654 (14)	0.0996 (8)	0.4272 (7)	0.143 (4)	0.60 (2)
C90	0.7388 (15)	0.4945 (8)	0.5226 (12)	0.124 (5)
D90	0.6980	0.4604	0.5763	0.148*
Cl91	0.7081 (5)	0.6026 (3)	0.5531 (3)	0.169 (2)
Cl92	0.9047 (7)	0.4615 (5)	0.4986 (5)	0.220 (3)
Cl93	0.6965 (8)	0.4755 (5)	0.4449 (6)	0.226 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01544 (16)	0.02144 (17)	0.01780 (16)	−0.00579 (12)	−0.00581 (12)	0.00129 (12)
Sn2	0.01716 (17)	0.02137 (17)	0.02117 (17)	−0.00468 (12)	−0.00731 (13)	−0.00201 (13)
Cl2	0.0337 (7)	0.0332 (7)	0.0328 (7)	−0.0078 (6)	−0.0101 (6)	0.0028 (6)
Cl1	0.0285 (6)	0.0367 (7)	0.0217 (6)	−0.0045 (5)	−0.0079 (5)	0.0009 (5)
O2	0.0244 (18)	0.0201 (17)	0.0257 (18)	−0.0057 (14)	−0.0100 (15)	0.0023 (14)
O1	0.0223 (17)	0.0207 (16)	0.0160 (15)	−0.0067 (13)	−0.0057 (13)	0.0001 (12)
C17	0.026 (3)	0.025 (3)	0.030 (3)	−0.006 (2)	−0.011 (2)	−0.005 (2)
N1	0.037 (3)	0.040 (3)	0.024 (2)	−0.013 (2)	−0.011 (2)	0.002 (2)
N2	0.029 (2)	0.024 (2)	0.028 (2)	−0.0054 (18)	−0.0125 (19)	−0.0030 (18)
C6	0.029 (3)	0.028 (3)	0.021 (2)	−0.009 (2)	−0.007 (2)	−0.003 (2)
C21	0.031 (3)	0.028 (3)	0.039 (3)	−0.009 (2)	−0.018 (2)	−0.001 (2)
C24	0.029 (3)	0.024 (3)	0.044 (3)	−0.007 (2)	−0.014 (3)	0.001 (2)
C1	0.025 (2)	0.022 (2)	0.028 (3)	−0.0080 (19)	−0.013 (2)	−0.002 (2)
C25	0.018 (2)	0.023 (2)	0.031 (3)	−0.0039 (18)	−0.010 (2)	−0.003 (2)
C10	0.016 (2)	0.028 (3)	0.024 (2)	−0.0062 (19)	−0.0041 (19)	0.006 (2)
C16	0.022 (2)	0.027 (3)	0.027 (3)	−0.008 (2)	−0.011 (2)	0.000 (2)
C2	0.027 (3)	0.027 (3)	0.030 (3)	−0.008 (2)	−0.014 (2)	0.001 (2)
C30	0.027 (3)	0.032 (3)	0.028 (3)	−0.010 (2)	−0.010 (2)	0.001 (2)
C3	0.034 (3)	0.042 (3)	0.026 (3)	−0.010 (2)	−0.016 (2)	0.002 (2)
C27	0.024 (3)	0.038 (3)	0.037 (3)	−0.006 (2)	−0.001 (2)	−0.008 (3)
C5	0.021 (3)	0.034 (3)	0.043 (3)	−0.005 (2)	−0.010 (2)	−0.004 (2)
C29	0.027 (3)	0.038 (3)	0.038 (3)	−0.003 (2)	−0.017 (2)	0.001 (2)
C22	0.028 (3)	0.024 (3)	0.041 (3)	−0.009 (2)	−0.017 (2)	0.002 (2)
C26	0.024 (3)	0.034 (3)	0.033 (3)	0.000 (2)	−0.009 (2)	−0.004 (2)
C15	0.020 (3)	0.031 (3)	0.042 (3)	−0.005 (2)	−0.009 (2)	−0.006 (2)
C7	0.032 (3)	0.038 (3)	0.026 (3)	−0.008 (2)	−0.012 (2)	0.000 (2)
C18	0.031 (3)	0.034 (3)	0.046 (3)	−0.016 (2)	−0.020 (3)	0.002 (3)
C23	0.043 (3)	0.036 (3)	0.027 (3)	−0.007 (3)	−0.011 (3)	−0.007 (2)
C4	0.035 (3)	0.040 (3)	0.039 (3)	−0.009 (3)	−0.024 (3)	0.003 (3)
C28	0.020 (3)	0.039 (3)	0.052 (4)	−0.001 (2)	−0.014 (3)	−0.009 (3)
C19	0.025 (3)	0.039 (3)	0.061 (4)	−0.009 (2)	−0.022 (3)	−0.005 (3)
C20	0.029 (3)	0.031 (3)	0.062 (4)	−0.002 (2)	−0.023 (3)	−0.003 (3)
C14	0.022 (3)	0.036 (3)	0.048 (4)	−0.010 (2)	−0.009 (3)	−0.005 (3)
C11	0.019 (3)	0.029 (3)	0.051 (4)	−0.010 (2)	0.000 (2)	−0.010 (3)
C13	0.017 (3)	0.046 (4)	0.053 (4)	−0.009 (2)	−0.004 (3)	0.007 (3)
C9	0.042 (4)	0.059 (4)	0.041 (4)	−0.021 (3)	−0.005 (3)	−0.003 (3)
C12	0.026 (3)	0.033 (3)	0.083 (5)	0.002 (3)	−0.007 (3)	−0.019 (3)
C8	0.063 (5)	0.046 (4)	0.042 (4)	−0.023 (3)	−0.025 (3)	0.018 (3)
C50	0.038 (4)	0.038 (4)	0.104 (7)	−0.004 (3)	−0.033 (4)	−0.007 (4)
Cl51	0.0641 (12)	0.0436 (9)	0.0749 (13)	−0.0156 (9)	−0.0282 (10)	0.0075 (9)
Cl52	0.0540 (11)	0.0742 (14)	0.0687 (13)	−0.0092 (10)	−0.0166 (10)	−0.0027 (11)
Cl53	0.0833 (18)	0.0798 (17)	0.175 (3)	−0.0312 (14)	−0.0204 (19)	−0.066 (2)
C60	0.037 (3)	0.050 (4)	0.050 (4)	−0.011 (3)	−0.005 (3)	−0.011 (3)
Cl61	0.0648 (13)	0.0799 (14)	0.0492 (11)	−0.0178 (11)	−0.0140 (9)	−0.0108 (10)
Cl62	0.0832 (15)	0.0562 (11)	0.0487 (11)	−0.0074 (10)	−0.0056 (10)	−0.0183 (9)
Cl63	0.0578 (12)	0.0408 (10)	0.1034 (18)	−0.0133 (9)	0.0011 (12)	−0.0153 (11)
C70A	0.093 (16)	0.078 (15)	0.087 (15)	−0.010 (10)	−0.025 (10)	−0.005 (9)
Cl75	0.126 (11)	0.062 (5)	0.080 (7)	0.011 (5)	−0.045 (6)	0.001 (5)
Cl74	0.154 (12)	0.120 (9)	0.094 (6)	−0.090 (9)	−0.070 (7)	0.038 (6)
Cl76	0.111 (9)	0.056 (4)	0.092 (7)	0.001 (5)	−0.026 (6)	0.014 (4)
C70	0.030 (6)	0.060 (7)	0.031 (5)	−0.006 (5)	−0.020 (5)	−0.008 (5)
Cl71	0.118 (7)	0.197 (10)	0.107 (6)	0.084 (7)	−0.083 (6)	−0.105 (7)
Cl72	0.062 (3)	0.223 (11)	0.115 (7)	0.007 (5)	−0.024 (3)	−0.065 (7)
Cl73	0.184 (11)	0.089 (4)	0.092 (5)	−0.005 (5)	−0.074 (7)	−0.001 (3)
C80	0.066 (18)	0.051 (16)	0.016 (8)	0.006 (13)	−0.008 (9)	−0.005 (9)
Cl81	0.088 (9)	0.144 (9)	0.064 (5)	0.038 (8)	−0.020 (6)	−0.048 (5)
Cl82	0.059 (5)	0.094 (5)	0.045 (3)	0.008 (3)	−0.032 (3)	−0.010 (3)
Cl83	0.118 (8)	0.109 (11)	0.156 (16)	−0.028 (8)	−0.019 (9)	−0.043 (10)
C80A	0.047 (8)	0.064 (11)	0.063 (9)	0.003 (7)	−0.007 (6)	−0.004 (7)
Cl84	0.078 (5)	0.121 (5)	0.049 (2)	0.027 (4)	−0.008 (3)	−0.013 (3)
Cl86	0.177 (13)	0.175 (10)	0.097 (5)	0.037 (10)	−0.063 (6)	0.006 (5)
Cl85	0.143 (8)	0.132 (7)	0.107 (6)	−0.035 (6)	−0.002 (5)	0.041 (5)
C90	0.134 (13)	0.068 (7)	0.140 (13)	−0.014 (8)	−0.024 (10)	0.014 (8)
Cl91	0.195 (5)	0.098 (3)	0.116 (3)	0.013 (3)	0.028 (3)	0.004 (2)
Cl92	0.197 (6)	0.222 (7)	0.193 (6)	0.037 (5)	−0.058 (5)	−0.032 (5)
Cl93	0.252 (8)	0.238 (8)	0.219 (7)	−0.082 (6)	−0.102 (7)	−0.001 (6)

Geometric parameters (Å, º) top

Sn1—O1ⁱ	2.031 (3)	C15—H15	0.9300
Sn1—O1	2.115 (3)	C7—H7A	0.9700
Sn1—C10	2.125 (5)	C7—H7B	0.9700
Sn1—C1	2.139 (5)	C18—C19	1.372 (9)
Sn1—O2	2.142 (3)	C18—H18	0.9300
Sn1—Sn1ⁱ	3.2649 (7)	C23—H23A	0.9600
Sn2—O1ⁱ	2.110 (3)	C23—H23B	0.9600
Sn2—O2	2.130 (4)	C23—H23C	0.9600
Sn2—C16	2.132 (5)	C4—H4	0.9300
Sn2—C25	2.144 (5)	C28—H28	0.9300
Sn2—N2	2.517 (4)	C19—C20	1.385 (9)
Sn2—Cl1	2.6017 (13)	C19—H19	0.9300
O2—H2	0.9300	C20—H20	0.9300
O1—Sn1ⁱ	2.031 (3)	C14—C13	1.359 (9)
O1—Sn2ⁱ	2.110 (3)	C14—H14	0.9300
C17—C18	1.377 (8)	C11—C12	1.396 (8)
C17—C16	1.404 (7)	C11—H11	0.9300
C17—C22	1.515 (7)	C13—C12	1.377 (9)
N1—C9	1.448 (8)	C13—H13	0.9300
N1—C8	1.490 (8)	C9—H9A	0.9600
N1—C7	1.502 (8)	C9—H9B	0.9600
N1—H1	0.9100	C9—H9C	0.9600
N2—C22	1.460 (7)	C12—H12	0.9300
N2—C24	1.472 (7)	C8—H8A	0.9600
N2—C23	1.486 (7)	C8—H8B	0.9600
C6—C1	1.377 (7)	C8—H8C	0.9600
C6—C5	1.387 (8)	C50—Cl53	1.732 (8)
C6—H6	0.9300	C50—Cl51	1.737 (9)
C21—C20	1.371 (8)	C50—Cl52	1.772 (9)
C21—C16	1.377 (8)	C50—D50	0.9800
C21—H21	0.9300	C60—Cl63	1.748 (7)
C24—H24A	0.9600	C60—Cl62	1.754 (7)
C24—H24B	0.9600	C60—Cl61	1.759 (8)
C24—H24C	0.9600	C60—D60	0.9800
C1—C2	1.411 (7)	C70A—Cl74	1.32 (5)
C25—C30	1.388 (8)	C70A—Cl76	1.67 (4)
C25—C26	1.395 (8)	C70A—Cl75	1.94 (5)
C10—C15	1.376 (7)	C70A—D70A	0.9800
C10—C11	1.383 (8)	Cl75—Cl74	2.47 (3)
C2—C3	1.418 (8)	C70—Cl71	1.636 (17)
C2—C7	1.494 (8)	C70—Cl73	1.776 (17)
C30—C29	1.373 (8)	C70—Cl72	1.793 (14)
C30—H30	0.9300	C70—D70	0.9800
C3—C4	1.356 (9)	C80—Cl81	1.58 (3)
C3—H3	0.9300	C80—Cl82	1.77 (3)
C27—C28	1.363 (9)	C80—Cl83	1.96 (4)
C27—C26	1.394 (8)	C80—D80	0.9800
C27—H27	0.9300	C80A—Cl85	1.61 (3)
C5—C4	1.398 (9)	C80A—Cl86	1.63 (3)
C5—H5	0.9300	C80A—Cl84	1.87 (3)
C29—C28	1.398 (9)	C80A—D80A	0.9800
C29—H29	0.9300	C90—Cl93	1.579 (18)
C22—H22A	0.9700	C90—Cl91	1.704 (14)
C22—H22B	0.9700	C90—Cl92	1.824 (17)
C26—H26	0.9300	C90—D90	0.9800
C15—C14	1.400 (8)

O1ⁱ—Sn1—O1	76.15 (14)	C27—C26—H26	119.8
O1ⁱ—Sn1—C10	117.58 (17)	C25—C26—H26	119.8
O1—Sn1—C10	98.97 (17)	C10—C15—C14	120.4 (5)
O1ⁱ—Sn1—C1	116.88 (17)	C10—C15—H15	119.8
O1—Sn1—C1	99.62 (16)	C14—C15—H15	119.8
C10—Sn1—C1	125.1 (2)	C2—C7—N1	115.8 (5)
O1ⁱ—Sn1—O2	74.63 (13)	C2—C7—H7A	108.3
O1—Sn1—O2	150.66 (13)	N1—C7—H7A	108.3
C10—Sn1—O2	96.77 (17)	C2—C7—H7B	108.3
C1—Sn1—O2	91.22 (16)	N1—C7—H7B	108.3
O1ⁱ—Sn1—Sn1ⁱ	38.98 (9)	H7A—C7—H7B	107.4
O1—Sn1—Sn1ⁱ	37.17 (9)	C19—C18—C17	121.5 (5)
C10—Sn1—Sn1ⁱ	112.90 (14)	C19—C18—H18	119.3
C1—Sn1—Sn1ⁱ	112.93 (14)	C17—C18—H18	119.3
O2—Sn1—Sn1ⁱ	113.57 (10)	N2—C23—H23A	109.5
O1ⁱ—Sn2—O2	73.31 (13)	N2—C23—H23B	109.5
O1ⁱ—Sn2—C16	100.53 (17)	H23A—C23—H23B	109.5
O2—Sn2—C16	92.56 (17)	N2—C23—H23C	109.5
O1ⁱ—Sn2—C25	100.96 (16)	H23A—C23—H23C	109.5
O2—Sn2—C25	95.58 (17)	H23B—C23—H23C	109.5
C16—Sn2—C25	158.41 (19)	C3—C4—C5	120.3 (5)
O1ⁱ—Sn2—N2	159.45 (14)	C3—C4—H4	119.9
O2—Sn2—N2	86.82 (14)	C5—C4—H4	119.9
C16—Sn2—N2	74.65 (17)	C27—C28—C29	119.8 (5)
C25—Sn2—N2	85.85 (17)	C27—C28—H28	120.1
O1ⁱ—Sn2—Cl1	87.05 (9)	C29—C28—H28	120.1
O2—Sn2—Cl1	159.94 (10)	C18—C19—C20	119.5 (5)
C16—Sn2—Cl1	86.94 (15)	C18—C19—H19	120.2
C25—Sn2—Cl1	92.07 (15)	C20—C19—H19	120.2
N2—Sn2—Cl1	112.25 (11)	C21—C20—C19	120.0 (6)
Sn2—O2—Sn1	103.23 (14)	C21—C20—H20	120.0
Sn2—O2—H2	128.4	C19—C20—H20	120.0
Sn1—O2—H2	128.4	C13—C14—C15	120.1 (5)
Sn1ⁱ—O1—Sn2ⁱ	107.90 (15)	C13—C14—H14	120.0
Sn1ⁱ—O1—Sn1	103.85 (14)	C15—C14—H14	120.0
Sn2ⁱ—O1—Sn1	147.88 (17)	C10—C11—C12	121.1 (5)
C18—C17—C16	118.4 (5)	C10—C11—H11	119.5
C18—C17—C22	121.4 (5)	C12—C11—H11	119.5
C16—C17—C22	120.0 (5)	C14—C13—C12	120.8 (5)
C9—N1—C8	110.4 (5)	C14—C13—H13	119.6
C9—N1—C7	112.3 (5)	C12—C13—H13	119.6
C8—N1—C7	112.7 (5)	N1—C9—H9A	109.5
C9—N1—H1	107.0	N1—C9—H9B	109.5
C8—N1—H1	107.0	H9A—C9—H9B	109.5
C7—N1—H1	107.0	N1—C9—H9C	109.5
C22—N2—C24	111.0 (4)	H9A—C9—H9C	109.5
C22—N2—C23	110.8 (4)	H9B—C9—H9C	109.5
C24—N2—C23	108.6 (4)	C13—C12—C11	119.0 (6)
C22—N2—Sn2	104.1 (3)	C13—C12—H12	120.5
C24—N2—Sn2	117.3 (3)	C11—C12—H12	120.5
C23—N2—Sn2	104.8 (3)	N1—C8—H8A	109.5
C1—C6—C5	121.8 (5)	N1—C8—H8B	109.5
C1—C6—H6	119.1	H8A—C8—H8B	109.5
C5—C6—H6	119.1	N1—C8—H8C	109.5
C20—C21—C16	120.5 (5)	H8A—C8—H8C	109.5
C20—C21—H21	119.7	H8B—C8—H8C	109.5
C16—C21—H21	119.7	Cl53—C50—Cl51	110.9 (4)
N2—C24—H24A	109.5	Cl53—C50—Cl52	112.4 (5)
N2—C24—H24B	109.5	Cl51—C50—Cl52	110.2 (4)
H24A—C24—H24B	109.5	Cl53—C50—D50	107.7
N2—C24—H24C	109.5	Cl51—C50—D50	107.7
H24A—C24—H24C	109.5	Cl52—C50—D50	107.7
H24B—C24—H24C	109.5	Cl63—C60—Cl62	110.9 (4)
C6—C1—C2	119.2 (5)	Cl63—C60—Cl61	110.8 (4)
C6—C1—Sn1	116.7 (4)	Cl62—C60—Cl61	109.5 (4)
C2—C1—Sn1	124.1 (4)	Cl63—C60—D60	108.6
C30—C25—C26	118.4 (5)	Cl62—C60—D60	108.6
C30—C25—Sn2	119.4 (4)	Cl61—C60—D60	108.6
C26—C25—Sn2	122.1 (4)	Cl74—C70A—Cl76	136 (3)
C15—C10—C11	118.7 (5)	Cl74—C70A—Cl75	97 (3)
C15—C10—Sn1	121.1 (4)	Cl76—C70A—Cl75	121 (2)
C11—C10—Sn1	120.1 (4)	Cl74—C70A—D70A	98.1
C21—C16—C17	120.0 (5)	Cl76—C70A—D70A	98.1
C21—C16—Sn2	122.4 (4)	Cl75—C70A—D70A	98.1
C17—C16—Sn2	117.6 (4)	C70A—Cl75—Cl74	32.0 (13)
C1—C2—C3	118.4 (5)	C70A—Cl74—Cl75	51 (2)
C1—C2—C7	122.9 (5)	Cl71—C70—Cl73	98.6 (11)
C3—C2—C7	118.6 (5)	Cl71—C70—Cl72	117.9 (10)
C29—C30—C25	121.0 (5)	Cl73—C70—Cl72	104.5 (8)
C29—C30—H30	119.5	Cl71—C70—D70	111.6
C25—C30—H30	119.5	Cl73—C70—D70	111.6
C4—C3—C2	121.2 (5)	Cl72—C70—D70	111.6
C4—C3—H3	119.4	Cl81—C80—Cl82	104.2 (16)
C2—C3—H3	119.4	Cl81—C80—Cl83	130 (2)
C28—C27—C26	120.3 (6)	Cl82—C80—Cl83	101.9 (18)
C28—C27—H27	119.9	Cl81—C80—D80	106.1
C26—C27—H27	119.9	Cl82—C80—D80	106.1
C6—C5—C4	119.1 (5)	Cl83—C80—D80	106.1
C6—C5—H5	120.5	Cl85—C80A—Cl86	117.5 (15)
C4—C5—H5	120.5	Cl85—C80A—Cl84	91.9 (16)
C30—C29—C28	120.0 (6)	Cl86—C80A—Cl84	105.2 (14)
C30—C29—H29	120.0	Cl85—C80A—D80A	113.3
C28—C29—H29	120.0	Cl86—C80A—D80A	113.3
N2—C22—C17	111.9 (4)	Cl84—C80A—D80A	113.3
N2—C22—H22A	109.2	Cl93—C90—Cl91	117.6 (10)
C17—C22—H22A	109.2	Cl93—C90—Cl92	114.9 (10)
N2—C22—H22B	109.2	Cl91—C90—Cl92	101.5 (9)
C17—C22—H22B	109.2	Cl93—C90—D90	107.4
H22A—C22—H22B	107.9	Cl91—C90—D90	107.4
C27—C26—C25	120.4 (6)	Cl92—C90—D90	107.4

Symmetry code: (i) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl2	0.93	2.21	3.079 (4)	156.0
N1—H1···Cl2	0.91	2.30	3.106 (5)	147.6

Experimental details

Crystal data
Chemical formula	[Sn₄(C₆H₅)₄Cl₂O₂(OH)₂(C₉H₁₃N)₂(C₉H₁₂N)₂]Cl₂·10CDCl₃
M_r	2733.56
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	11.9279 (5), 15.4080 (12), 15.9651 (14)
α, β, γ (°)	83.752 (7), 68.178 (4), 76.339 (5)
V (Å³)	2646.1 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.84
Crystal size (mm)	0.28 × 0.26 × 0.21

Data collection
Diffractometer	Bruker–Nonius KappaCCD area-detector
Absorption correction	Gaussian (Coppens, 1970)
T_min, T_max	0.758, 0.820
No. of measured, independent and observed [I > 2σ(I)] reflections	51386, 12052, 9459
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.146, 1.08
No. of reflections	12052
No. of parameters	598
No. of restraints	12
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0647P)² + 12.7718P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.95, −1.15

Computer programs: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl2	0.93	2.21	3.079 (4)	156.0
N1—H1···Cl2	0.91	2.30	3.106 (5)	147.6

Acknowledgements

The authors would like to thank the Ministry of Education, Youth and Sports of the Czech Republic (project MSM 0021627501) and the Czech Science Foundation (project P207/10/P092) for the financial support of this work.

References

Beckmann, J., Jurkschat, K., Rabe, S., Schurmann, M. & Dakternieks, D. (2001). Z. Anorg. Allg. Chem. 627, 458–464. Web of Science CSD CrossRef CAS Google Scholar
Coppens, P. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 255–270. Copenhagen: Munksgaard. Google Scholar
Cox, M. J. & Tiekink, E. R. T. (1994). Z. Kristallogr. 209, 622–624. CrossRef CAS Web of Science Google Scholar
Hooft, R. W. (1998). COLLECT, Nonius BV, Delft, The Netherlands. Google Scholar
Jambor, R., Růžička, A., Brus, J., Císařová, I. & Holeček, J. (2001). Inorg. Chem. Commun. 4, 257–260. Web of Science CSD CrossRef CAS Google Scholar
Kresinski, R. A., Staples, R. J. & Fackler, J. P. (1994). Acta Cryst. C50, 40–41. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, m593. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mohamed, E. M., Panchanatheswaran, K., Low, J. N. & Glidewell, C. (2004). Acta Cryst. E60, m489–m491. Web of Science CSD CrossRef IUCr Journals Google Scholar
Novák, P., Císařová, I., Kolářová, L., Růžička, A. & Holeček, J. (2007). J. Organomet. Chem. 692, 4287–4296. Google Scholar
Novák, P., Padělková, Z., Císařová, I., Kolářová, L., Růžička, A. & Holeček, J. (2006). Appl. Organomet. Chem. 20, 226–232. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Padělková, Z., Weidlich, T., Císařová, I. & Růžička, A. (2009). Appl. Organomet. Chem. 23, 253–257. Google Scholar
Padělková, Z., Weidlich, T., Kolářová, L., Eisner, A., Císařová, I., Zevaco, T. A. & Růžička, A. (2007). J. Organomet. Chem. 692, 5633–5645. Google Scholar
Puff, H., Bung, I., Friedrichs, E. & Jansen, A. (1983). J. Organomet. Chem. 254, 23–32. CSD CrossRef CAS Web of Science 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
Švec, P., Černošková, E., Padělková, Z., Růžička, A. & Holeček, J. (2010). J. Organomet. Chem. 695, 2475–2485. Google Scholar
Švec, P., Padělková, Z., Růžička, A., Weidlich, T., Dušek, L. & Plasseraud, L. (2011). J. Organomet. Chem. 696, 676–686. Google Scholar
Thoonen, S. H. L., van Hoek, H., de Wolf, E., Lutz, M., Spek, A. L., Deelman, B.-J. & van Koten, G. (2006). J. Organomet. Chem. 691, 1544–1553. Web of Science CSD CrossRef CAS Google Scholar
Tiekink, E. R. T. (1991). Acta Cryst. C47, 661–662. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Varga, R. A. & Silvestru, C. (2007). Acta Cryst. C63, m48–m50. Web of Science CSD CrossRef IUCr Journals Google Scholar
Vollano, J. F., Day, R. O. & Holmes, R. R. (1984). Organometallics, 3, 745–750. CSD CrossRef CAS Web of Science Google Scholar
Zhang, Q.-J., Yin, H.-D., Wen, L.-Y. & Wang, D.-Q. (2009). Acta Cryst. E65, m1494. Web of Science CrossRef IUCr Journals Google Scholar

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