supplementary materials


wm2692 scheme

Acta Cryst. (2012). E68, m1380-m1381    [ doi:10.1107/S1600536812042894 ]

Poly[dibutylammonium [nonamethylbis([mu]3-sulfato-[kappa]3O:O':O'')tristannate(IV)]]

T. Diop, L. Diop and A. van der Lee

Abstract top

In the structure of the title coordination polymer, {(C8H20N)[Sn3(CH3)9(SO4)2]}n, each of the three SnIV atoms is coordinated in a trigonal-bipyramidal manner by three methyl groups in the equatorial plane and by two O atoms of SO42- anions in the axial positions. The [mu]3-bridging mode of the sulfate anions leads to the formation of corrugated anionic layers parallel to (100). The uncoordinating O atom of one of the two SO42- anions is N-H...O hydrogen-bonded to the dibutylammonium cation interconnecting the anionic sheets. The structure is partially disordered. The dibutyl ammonium ion is found on two positions with an occupancy ratio of 0.525 (10):0.475 (10), and one sulfate group with three connecting trimethyl stannyl groups is also positionally disordered over two sets of sites with an occupancy ratio of 0.725 (4):0.275 (4).

Comment top

Various applications of organotin(IV) compounds explain the focus of research teams, including ours, to the search and characterisation of new organotin(IV) compounds, e.g. Evans & Karpel (1985); Basu et al. (2005); Kapoor et al. (2005); Samuel et al. (2002). In the scope of our research on the coordination ability of oxyanions (Molloy et al., 1989; Diop et al., 2002) and our interest to synthesize new organotin(IV) derivatives for biological tests, we elucidate here the structure of the title compound, (C8H20N)[(Sn(CH3)3)3(SO4)2], (I).

Compound (I) has a polymeric structure consisting of three O2SnC3 moieties, and two different tridentate sulfate ligands (Fig. 1). In the two-dimensional polymeric structure that extends parallel to (100) (Fig. 2) all tin(IV) atoms are five-coordinate, with the trigonal (CH3)3Sn units axially bridged through sulfate groups. The angles between the apical positions within the trigonal-bipyramidal arrangement indicate a slight deviation from linearity for Sn1 and Sn2 (O1—Sn1—O7 = 172.44 (8)°; O8—Sn2—O2 = 176.59 (11)°) and a considerable deviation for Sn3 (O4—Sn3—O5 = 168.64 (10)°). The Sn—O bonds are in the excepted range [2.262 (2)–2.305 (2) Å] and are shorter than the Sn—O distances in (Bu4N)HSO4.Sn(CH3)3Cl [2.450 (5)] (Diallo et al., 2009). The dibutylammonium cation connects adjacent anionic layers through N—H···O hydrogen bonding into a three-dimensional network structure (Fig. 3).

Related literature top

For applications of tin(IV) compounds, see: Basu et al. (2005); Evans & Karpel (1985); Samuel et al. (2002); Kapoor et al. (2005). For related organotin(IV) compounds, see: Molloy et al. (1989); Diop et al. (2002) Diallo et al. (2009).

Experimental top

(Bu2NH2)2SO4.H2O (L) was obtained on mixing a water solution of NH2SO3H (0.15 g, 1.5 mmol) with Bu2NH2 (0.78 g, 3 mmol). Hydrolysis of NH2SO3H in basic media has yielded the sulfate. The title compound has been obtained by reacting (L) (0.15 g, 0.4 mmol) with trimethyltin chloride (0.16 g, 0.8 mmol) in ethanol. Slow solvent evaporation yielded colourless crystals. SnMe3Cl, the acid NH2SO3H and Bu2NH2 were purchased from Aldrich and used without further purification.

Refinement top

Three reflections, (0 1 1), (1 0 0) and (1 1 1), were obstructed by the beam stop and were omitted from the refinement. Disorder is observed for one of the sulfate groups and for the dibutyl ammonium ion. The disorder of the sulfate group extends to the neighboring trimethyl stannyl groups and the occupancy ratio refined to 0.725 (4):0.275 (4). The occupancy ratio for the dibutyl ammonium ion is 0.525 (10):0.475 (10). All equivalent disordered moieties were restrained to have similar geometries (SAME command in SHELXTL). Equivalent methyl groups of trimethyl stannyl groups were restrained to have similar ADPs, as were Sn1 and Sn1B and Sn2 and Sn2B. The disordered atoms N1, N1B, C13, C13B, C14 and C14B of the dibutyl ammonium ion were restrained to be approximately isotropic (ISOR 0.005 command in SHELXTL). Methyl H atoms were placed onto calculated positions and refined using a riding model, with C—H distances of 0.98 Å and Uiso(H)= 1.5Ueq(C); methylene H atoms were refined with C—H distances of 0.99 Å and Uiso(H)= 1.2Ueq(C); ammonium H atoms were refined with N—H distances of 0.90 Å and Uiso(H)= 1.2Ueq(N).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXLE (Hübschle et al., 2011); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip (2010).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the structure of compound (I) with displacement ellipsoids drawn at the 50° probability level. The minor components of the disordered parts within the structure are not shown.
[Figure 2] Fig. 2. The two-dimensional [(SnMe3)3(SO4)2]- anionic sheet structure of (I). Hydrogen atoms and the Bu2NH2+ cations have been omitted for clarity. The minor components of the disordered parts within the structure are not shown.
[Figure 3] Fig. 3. The linking of the sheets through N—H···O hydrogen bonds between the Bu2NH2+ cations and the stannate(IV) sheets (red dotted lines). Only H atoms involved in hydrogen bond interactions are shown for the sake of clarity.
Poly[dibutylammonium [nonamethylbis(µ3-sulfato- κ3O:O':O'')tristannate(IV)]] top
Crystal data top
(C8H20N)[Sn3(CH3)9(SO4)2]F(000) = 1608
Mr = 813.75Dx = 1.693 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9693 reflections
a = 11.8847 (2) Åθ = 2.6–27.5°
b = 18.2884 (3) ŵ = 2.49 mm1
c = 15.3949 (2) ÅT = 173 K
β = 107.380 (1)°Prism, colourless
V = 3193.35 (9) Å30.06 × 0.04 × 0.04 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
7234 independent reflections
Radiation source: fine-focus sealed tube6265 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
phi and ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS, Bruker, 2003)
h = 1515
Tmin = 0.865, Tmax = 0.907k = 2323
69889 measured reflectionsl = 1819
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)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.045H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0164P)2 + 2.1021P]
where P = (Fo2 + 2Fc2)/3
7234 reflections(Δ/σ)max = 0.004
463 parametersΔρmax = 0.76 e Å3
77 restraintsΔρmin = 0.46 e Å3
Crystal data top
(C8H20N)[Sn3(CH3)9(SO4)2]V = 3193.35 (9) Å3
Mr = 813.75Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.8847 (2) ŵ = 2.49 mm1
b = 18.2884 (3) ÅT = 173 K
c = 15.3949 (2) Å0.06 × 0.04 × 0.04 mm
β = 107.380 (1)°
Data collection top
Bruker SMART CCD
diffractometer
7234 independent reflections
Absorption correction: multi-scan
(SADABS, Bruker, 2003)
6265 reflections with I > 2σ(I)
Tmin = 0.865, Tmax = 0.907Rint = 0.027
69889 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.020H-atom parameters constrained
wR(F2) = 0.045Δρmax = 0.76 e Å3
S = 1.06Δρmin = 0.46 e Å3
7234 reflectionsAbsolute structure: ?
463 parametersFlack parameter: ?
77 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
Sn10.19280 (7)0.52408 (7)0.43977 (5)0.02502 (12)0.725 (4)
C10.0484 (7)0.5964 (5)0.4208 (8)0.0473 (16)0.725 (4)
H1A0.04670.63050.37130.071*0.725 (4)
H1B0.05680.62380.47700.071*0.725 (4)
H1C0.02510.56830.40520.071*0.725 (4)
C20.3636 (5)0.5703 (3)0.4693 (8)0.0441 (16)0.725 (4)
H2A0.41380.55070.52720.066*0.725 (4)
H2B0.35820.62360.47390.066*0.725 (4)
H2C0.39770.55810.42060.066*0.725 (4)
C30.1752 (8)0.4094 (2)0.4284 (8)0.0402 (10)0.725 (4)
H3A0.21780.39120.38720.060*0.725 (4)
H3B0.09160.39660.40410.060*0.725 (4)
H3C0.20800.38710.48850.060*0.725 (4)
Sn1B0.1839 (2)0.54067 (10)0.43984 (16)0.02502 (12)0.275 (4)
C1B0.0361 (19)0.6038 (15)0.436 (2)0.0473 (16)0.275 (4)
H1D0.00520.58910.48550.071*0.275 (4)
H1E0.02470.59640.37740.071*0.275 (4)
H1F0.05830.65560.44260.071*0.275 (4)
C2B0.3517 (14)0.5897 (12)0.467 (2)0.0441 (16)0.275 (4)
H2D0.35350.62100.41610.066*0.275 (4)
H2E0.41190.55160.47600.066*0.275 (4)
H2F0.36740.61930.52270.066*0.275 (4)
C3B0.181 (2)0.4250 (7)0.426 (2)0.0402 (10)0.275 (4)
H3D0.14750.41200.36140.060*0.275 (4)
H3E0.13260.40370.46080.060*0.275 (4)
H3F0.26150.40590.44840.060*0.275 (4)
Sn20.24211 (11)0.75268 (7)0.20340 (9)0.02730 (14)0.725 (4)
C40.3133 (10)0.7154 (8)0.1007 (7)0.0483 (9)0.725 (4)
H4A0.30140.66250.09290.072*0.725 (4)
H4B0.39790.72630.11830.072*0.725 (4)
H4C0.27370.74020.04320.072*0.725 (4)
C50.0582 (5)0.7575 (10)0.1795 (8)0.0491 (14)0.725 (4)
H5A0.03960.74620.23590.074*0.725 (4)
H5B0.01960.72190.13250.074*0.725 (4)
H5C0.02990.80680.15900.074*0.725 (4)
C60.3555 (10)0.7844 (10)0.3327 (5)0.0519 (16)0.725 (4)
H6A0.32500.76500.38060.078*0.725 (4)
H6B0.35900.83790.33660.078*0.725 (4)
H6C0.43470.76490.34050.078*0.725 (4)
Sn2B0.2528 (3)0.7522 (2)0.1900 (2)0.02730 (14)0.275 (4)
C4B0.323 (3)0.711 (2)0.089 (2)0.0483 (9)0.275 (4)
H4D0.38670.67710.11720.072*0.275 (4)
H4E0.35290.75190.06140.072*0.275 (4)
H4F0.26050.68580.04280.072*0.275 (4)
C5B0.0684 (13)0.759 (3)0.168 (2)0.0491 (14)0.275 (4)
H5D0.02910.77270.10500.074*0.275 (4)
H5E0.05210.79640.20890.074*0.275 (4)
H5F0.03870.71170.18150.074*0.275 (4)
C6B0.365 (3)0.784 (3)0.3199 (15)0.0519 (16)0.275 (4)
H6D0.32420.82030.34690.078*0.275 (4)
H6E0.43720.80610.31290.078*0.275 (4)
H6F0.38520.74140.35960.078*0.275 (4)
Sn30.48425 (13)0.49901 (8)0.23557 (10)0.02997 (17)0.725 (4)
C70.4615 (6)0.4916 (5)0.0949 (4)0.0587 (14)0.725 (4)
H7A0.38800.46550.06520.088*0.725 (4)
H7B0.52800.46500.08480.088*0.725 (4)
H7C0.45780.54090.06910.088*0.725 (4)
C80.4371 (7)0.4042 (3)0.2953 (7)0.0501 (14)0.725 (4)
H8A0.41470.41800.34940.075*0.725 (4)
H8B0.50430.37060.31280.075*0.725 (4)
H8C0.37030.38020.25140.075*0.725 (4)
C90.5460 (8)0.5971 (3)0.3069 (4)0.0451 (17)0.725 (4)
H9A0.59420.58550.36900.068*0.725 (4)
H9B0.47860.62720.30910.068*0.725 (4)
H9C0.59360.62410.27550.068*0.725 (4)
Sn3B0.4842 (3)0.4875 (2)0.2556 (2)0.0272 (4)0.275 (4)
C7B0.442 (2)0.4955 (16)0.1121 (9)0.0587 (14)0.275 (4)
H7D0.42760.44650.08530.088*0.275 (4)
H7E0.50730.51840.09600.088*0.275 (4)
H7F0.37050.52530.08860.088*0.275 (4)
C8B0.453 (2)0.3869 (10)0.306 (2)0.0501 (14)0.275 (4)
H8D0.44580.34930.25940.075*0.275 (4)
H8E0.38050.38910.32340.075*0.275 (4)
H8F0.51950.37460.35980.075*0.275 (4)
C9B0.545 (3)0.5850 (10)0.3299 (14)0.0451 (17)0.275 (4)
H9D0.62880.59210.33550.068*0.275 (4)
H9E0.53530.58100.39070.068*0.275 (4)
H9F0.49960.62670.29780.068*0.275 (4)
S10.22744 (4)0.56106 (3)0.66835 (3)0.02531 (11)
S20.20127 (4)0.56894 (3)0.22152 (4)0.02637 (11)
O10.21738 (14)0.51080 (8)0.59177 (10)0.0346 (3)
O20.25042 (13)0.63526 (8)0.63914 (10)0.0349 (3)
O30.12102 (12)0.56030 (9)0.69614 (11)0.0379 (4)
O40.32836 (12)0.53761 (8)0.74657 (10)0.0336 (3)
O50.29205 (19)0.53491 (14)0.1876 (2)0.0456 (8)0.725 (4)
O60.0959 (3)0.5803 (2)0.1412 (3)0.0323 (8)0.725 (4)
O70.1694 (3)0.52091 (15)0.28571 (15)0.0426 (7)0.725 (4)
O80.2434 (5)0.6394 (3)0.2647 (4)0.0340 (9)0.725 (4)
O5B0.2927 (4)0.5082 (3)0.2478 (4)0.0258 (15)0.275 (4)
O6B0.1308 (9)0.5633 (6)0.1333 (8)0.035 (2)0.275 (4)
O7B0.1313 (4)0.5615 (4)0.2883 (4)0.0275 (14)0.275 (4)
O8B0.2728 (12)0.6375 (8)0.2442 (10)0.037 (3)0.275 (4)
C100.1466 (18)0.2765 (11)0.122 (2)0.118 (10)0.525 (10)
H10A0.20850.31020.11680.177*0.525 (10)
H10B0.14960.23180.08720.177*0.525 (10)
H10C0.15900.26410.18580.177*0.525 (10)
C110.0283 (16)0.3123 (10)0.0838 (13)0.078 (6)0.525 (10)
H11A0.03340.28020.09440.093*0.525 (10)
H11B0.01130.31870.01730.093*0.525 (10)
C120.0245 (14)0.3855 (8)0.1273 (15)0.055 (5)0.525 (10)
H12A0.04330.37890.19400.066*0.525 (10)
H12B0.08580.41750.11600.066*0.525 (10)
C130.0918 (10)0.4225 (7)0.0928 (10)0.046 (3)0.525 (10)
H13A0.15500.38930.09870.056*0.525 (10)
H13B0.10760.43470.02770.056*0.525 (10)
N10.0914 (11)0.4906 (6)0.1463 (10)0.035 (2)0.525 (10)
H1G0.09310.47770.20370.042*0.525 (10)
H1H0.02380.51720.15250.042*0.525 (10)
C140.1959 (10)0.5347 (5)0.0970 (8)0.046 (2)0.525 (10)
H14A0.26820.50580.09110.055*0.525 (10)
H14B0.19200.54540.03500.055*0.525 (10)
C150.2040 (12)0.6053 (6)0.1442 (8)0.052 (3)0.525 (10)
H15A0.12750.63110.15770.062*0.525 (10)
H15B0.21870.59450.20290.062*0.525 (10)
C160.3018 (10)0.6557 (5)0.0880 (8)0.082 (3)0.525 (10)
H16A0.28730.66600.02910.098*0.525 (10)
H16B0.37820.62980.07480.098*0.525 (10)
C170.3111 (7)0.7268 (4)0.1333 (8)0.091 (3)0.525 (10)
H17A0.37100.75750.09170.136*0.525 (10)
H17B0.23480.75190.14950.136*0.525 (10)
H17C0.33370.71760.18860.136*0.525 (10)
C10B0.1311 (16)0.2763 (11)0.118 (2)0.089 (8)0.475 (10)
H10D0.20310.30410.12230.134*0.475 (10)
H10E0.12690.23410.07760.134*0.475 (10)
H10F0.13220.25930.17830.134*0.475 (10)
C11B0.0255 (19)0.3243 (11)0.0792 (15)0.075 (6)0.475 (10)
H11C0.04670.29460.07030.090*0.475 (10)
H11D0.02640.34210.01870.090*0.475 (10)
C12B0.0191 (12)0.3895 (9)0.1379 (17)0.049 (5)0.475 (10)
H12C0.09200.41890.14870.059*0.475 (10)
H12D0.01420.37230.19760.059*0.475 (10)
C13B0.0881 (12)0.4379 (7)0.0930 (13)0.055 (4)0.475 (10)
H13C0.08440.45240.03200.066*0.475 (10)
H13D0.16030.40820.08420.066*0.475 (10)
N1B0.0993 (13)0.5058 (7)0.1445 (11)0.036 (2)0.475 (10)
H1I0.10100.49290.20190.043*0.475 (10)
H1J0.03170.53240.15070.043*0.475 (10)
C14B0.2004 (10)0.5555 (6)0.1088 (8)0.043 (2)0.475 (10)
H14C0.27460.52770.09870.052*0.475 (10)
H14D0.19850.57530.04940.052*0.475 (10)
C15B0.1988 (14)0.6180 (8)0.1730 (8)0.045 (2)0.475 (10)
H15C0.12760.64830.18030.054*0.475 (10)
H15D0.19700.59880.23360.054*0.475 (10)
C16B0.3104 (8)0.6649 (6)0.1338 (8)0.069 (3)0.475 (10)
H16C0.38000.63220.11740.082*0.475 (10)
H16D0.31880.69850.18190.082*0.475 (10)
C17B0.3107 (9)0.7085 (6)0.0530 (7)0.104 (4)0.475 (10)
H17D0.23930.73860.06710.155*0.475 (10)
H17E0.38030.74010.03600.155*0.475 (10)
H17F0.31250.67560.00230.155*0.475 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02974 (15)0.0191 (3)0.02525 (9)0.0002 (2)0.00679 (9)0.0016 (2)
C10.040 (2)0.039 (2)0.054 (4)0.0089 (15)0.0003 (19)0.003 (2)
C20.0365 (18)0.062 (4)0.0331 (15)0.011 (2)0.0091 (15)0.002 (3)
C30.0535 (16)0.027 (2)0.0405 (15)0.004 (2)0.0147 (16)0.012 (3)
Sn1B0.02974 (15)0.0191 (3)0.02525 (9)0.0002 (2)0.00679 (9)0.0016 (2)
C1B0.040 (2)0.039 (2)0.054 (4)0.0089 (15)0.0003 (19)0.003 (2)
C2B0.0365 (18)0.062 (4)0.0331 (15)0.011 (2)0.0091 (15)0.002 (3)
C3B0.0535 (16)0.027 (2)0.0405 (15)0.004 (2)0.0147 (16)0.012 (3)
Sn20.0307 (2)0.02653 (8)0.0250 (4)0.00035 (13)0.00894 (16)0.0003 (2)
C40.058 (3)0.042 (3)0.055 (3)0.0052 (16)0.0309 (17)0.008 (2)
C50.0383 (17)0.040 (2)0.074 (3)0.0031 (19)0.0245 (17)0.005 (3)
C60.072 (3)0.0378 (16)0.033 (3)0.005 (2)0.004 (2)0.002 (3)
Sn2B0.0307 (2)0.02653 (8)0.0250 (4)0.00035 (13)0.00894 (16)0.0003 (2)
C4B0.058 (3)0.042 (3)0.055 (3)0.0052 (16)0.0309 (17)0.008 (2)
C5B0.0383 (17)0.040 (2)0.074 (3)0.0031 (19)0.0245 (17)0.005 (3)
C6B0.072 (3)0.0378 (16)0.033 (3)0.005 (2)0.004 (2)0.002 (3)
Sn30.02517 (15)0.0352 (4)0.0292 (5)0.0003 (2)0.0076 (3)0.0033 (3)
C70.045 (3)0.096 (3)0.032 (3)0.000 (2)0.0078 (19)0.003 (3)
C80.041 (3)0.056 (4)0.052 (3)0.009 (3)0.011 (2)0.004 (3)
C90.0316 (13)0.044 (3)0.061 (4)0.005 (2)0.016 (3)0.016 (3)
Sn3B0.0278 (4)0.0324 (9)0.0210 (10)0.0030 (5)0.0068 (6)0.0003 (6)
C7B0.045 (3)0.096 (3)0.032 (3)0.000 (2)0.0078 (19)0.003 (3)
C8B0.041 (3)0.056 (4)0.052 (3)0.009 (3)0.011 (2)0.004 (3)
C9B0.0316 (13)0.044 (3)0.061 (4)0.005 (2)0.016 (3)0.016 (3)
S10.0256 (2)0.0280 (3)0.0235 (3)0.00012 (19)0.0090 (2)0.0016 (2)
S20.0255 (2)0.0269 (3)0.0264 (3)0.00036 (19)0.0073 (2)0.0025 (2)
O10.0516 (9)0.0286 (8)0.0245 (8)0.0029 (7)0.0130 (7)0.0031 (6)
O20.0423 (8)0.0288 (8)0.0358 (9)0.0019 (6)0.0148 (7)0.0030 (7)
O30.0281 (7)0.0505 (10)0.0378 (9)0.0058 (7)0.0143 (7)0.0074 (8)
O40.0269 (7)0.0415 (9)0.0307 (9)0.0042 (6)0.0061 (6)0.0021 (7)
O50.0299 (12)0.0513 (16)0.0538 (19)0.0044 (10)0.0098 (11)0.0087 (14)
O60.0282 (18)0.035 (2)0.0298 (16)0.0027 (13)0.0022 (13)0.0038 (13)
O70.0663 (19)0.0372 (15)0.0227 (13)0.0174 (14)0.0108 (12)0.0007 (11)
O80.044 (2)0.0272 (14)0.028 (2)0.0040 (15)0.0069 (14)0.0019 (13)
O5B0.021 (2)0.022 (3)0.035 (4)0.000 (2)0.009 (2)0.000 (2)
O6B0.037 (6)0.039 (6)0.023 (4)0.003 (4)0.001 (4)0.005 (3)
O7B0.019 (3)0.041 (4)0.023 (3)0.006 (2)0.008 (2)0.002 (3)
O8B0.042 (6)0.030 (4)0.032 (7)0.003 (4)0.001 (4)0.008 (4)
C100.127 (15)0.070 (12)0.16 (2)0.020 (10)0.040 (13)0.037 (12)
C110.092 (12)0.070 (8)0.085 (13)0.036 (7)0.047 (10)0.043 (8)
C120.077 (9)0.051 (8)0.038 (7)0.007 (6)0.019 (6)0.005 (5)
C130.056 (4)0.055 (4)0.029 (4)0.024 (3)0.013 (3)0.015 (3)
N10.031 (3)0.038 (4)0.029 (3)0.006 (2)0.000 (2)0.004 (3)
C140.049 (3)0.045 (4)0.041 (4)0.002 (3)0.009 (3)0.000 (3)
C150.041 (3)0.047 (6)0.061 (8)0.014 (4)0.008 (5)0.015 (5)
C160.073 (5)0.081 (6)0.093 (8)0.008 (4)0.028 (6)0.006 (6)
C170.082 (5)0.047 (5)0.142 (10)0.001 (3)0.031 (5)0.006 (5)
C10B0.069 (8)0.092 (15)0.108 (15)0.037 (9)0.029 (8)0.039 (11)
C11B0.095 (13)0.053 (7)0.061 (10)0.010 (7)0.001 (7)0.004 (7)
C12B0.053 (7)0.058 (9)0.041 (7)0.027 (6)0.020 (5)0.024 (5)
C13B0.062 (5)0.058 (5)0.044 (5)0.023 (4)0.013 (3)0.006 (4)
N1B0.038 (4)0.041 (4)0.031 (4)0.005 (3)0.013 (3)0.006 (3)
C14B0.035 (3)0.049 (5)0.038 (4)0.004 (3)0.001 (3)0.004 (4)
C15B0.044 (4)0.039 (5)0.047 (6)0.002 (4)0.005 (4)0.008 (4)
C16B0.044 (4)0.065 (7)0.095 (8)0.006 (3)0.019 (5)0.014 (6)
C17B0.134 (9)0.063 (6)0.104 (8)0.016 (5)0.020 (6)0.020 (6)
Geometric parameters (Å, º) top
Sn1—C12.117 (5)C8B—H8F0.9800
Sn1—C22.119 (5)C9B—H9D0.9800
Sn1—C32.110 (4)C9B—H9E0.9800
Sn1—O12.2829 (17)C9B—H9F0.9800
Sn1—O72.305 (2)S1—O31.4513 (15)
Sn1B—C1B2.088 (13)S1—O11.4714 (15)
Sn1B—C2B2.111 (13)S1—O21.4803 (15)
Sn1B—C3B2.126 (13)S1—O41.4866 (15)
Sn1B—O12.317 (3)S2—O6B1.370 (11)
Sn1B—O7B2.260 (6)S2—O71.455 (2)
Sn2—C42.117 (5)S2—O81.468 (5)
Sn2—C52.107 (5)S2—O51.470 (2)
Sn2—C62.124 (5)S2—O61.489 (4)
Sn2—O2i2.2906 (19)S2—O8B1.496 (13)
Sn2—O82.274 (6)S2—O7B1.510 (5)
Sn2B—C4B2.100 (14)S2—O5B1.522 (5)
Sn2B—C5B2.120 (14)O2—Sn2Biii2.200 (4)
Sn2B—C6B2.128 (14)O2—Sn2iii2.2906 (19)
Sn2B—O2i2.200 (4)O4—Sn3ii2.262 (2)
Sn2B—O8B2.243 (15)O4—Sn3Bii2.285 (4)
Sn3—C72.106 (5)C10—C111.502 (12)
Sn3—C82.115 (5)C10—H10A0.9800
Sn3—C92.117 (5)C10—H10B0.9800
Sn3—O4ii2.262 (2)C10—H10C0.9800
Sn3—O52.277 (3)C11—C121.506 (11)
Sn3B—C7B2.119 (13)C11—H11A0.9900
Sn3B—C8B2.074 (13)C11—H11B0.9900
Sn3B—C9B2.125 (13)C12—C131.487 (11)
Sn3B—O4ii2.285 (4)C12—H12A0.9900
Sn3B—O5B2.274 (6)C12—H12B0.9900
C1—H1A0.9800C13—N11.491 (10)
C1—H1B0.9800C13—H13A0.9900
C1—H1C0.9800C13—H13B0.9900
C2—H2A0.9800N1—C141.486 (10)
C2—H2B0.9800N1—H1G0.9206
C2—H2C0.9800N1—H1H0.9195
C3—H3A0.9800N1—H1I0.8986
C3—H3B0.9800N1—H1J1.0317
C3—H3C0.9800C14—C151.498 (9)
C1B—H1D0.9800C14—H14A0.9900
C1B—H1E0.9800C14—H14B0.9900
C1B—H1F0.9800C15—C161.533 (10)
C2B—H2D0.9800C15—H15A0.9900
C2B—H2E0.9800C15—H15B0.9900
C2B—H2F0.9800C16—C171.496 (11)
C3B—H3D0.9800C16—H16A0.9900
C3B—H3E0.9800C16—H16B0.9900
C3B—H3F0.9800C17—H17A0.9800
C4—H4A0.9800C17—H17B0.9800
C4—H4B0.9800C17—H17C0.9800
C4—H4C0.9800C10B—C11B1.501 (13)
C5—H5A0.9800C10B—H10D0.9800
C5—H5B0.9800C10B—H10E0.9800
C5—H5C0.9800C10B—H10F0.9800
C6—H6A0.9800C11B—C12B1.511 (13)
C6—H6B0.9800C11B—H11C0.9900
C6—H6C0.9800C11B—H11D0.9900
C4B—H4D0.9800C12B—C13B1.535 (12)
C4B—H4E0.9800C12B—H12C0.9900
C4B—H4F0.9800C12B—H12D0.9900
C5B—H5D0.9800C13B—N1B1.502 (11)
C5B—H5E0.9800C13B—H13C0.9900
C5B—H5F0.9800C13B—H13D0.9900
C6B—H6D0.9800N1B—C14B1.475 (10)
C6B—H6E0.9800N1B—H1G1.0296
C6B—H6F0.9800N1B—H1H0.8937
C7—H7A0.9800N1B—H1I0.9207
C7—H7B0.9800N1B—H1J0.9195
C7—H7C0.9800C14B—C15B1.507 (10)
C8—H8A0.9800C14B—H14C0.9900
C8—H8B0.9800C14B—H14D0.9900
C8—H8C0.9800C15B—C16B1.542 (10)
C9—H9A0.9800C15B—H15C0.9900
C9—H9B0.9800C15B—H15D0.9900
C9—H9C0.9800C16B—C17B1.477 (11)
C7B—H7D0.9800C16B—H16C0.9900
C7B—H7E0.9800C16B—H16D0.9900
C7B—H7F0.9800C17B—H17D0.9800
C8B—H8D0.9800C17B—H17E0.9800
C8B—H8E0.9800C17B—H17F0.9800
C3—Sn1—C1123.6 (4)O7—S2—O8110.2 (2)
C3—Sn1—C2118.7 (3)O7—S2—O5110.70 (17)
C1—Sn1—C2117.7 (3)O8—S2—O5110.19 (18)
C3—Sn1—O187.6 (3)O7—S2—O6108.9 (2)
C1—Sn1—O193.3 (3)O8—S2—O6110.0 (3)
C2—Sn1—O190.1 (3)O5—S2—O6106.81 (17)
C3—Sn1—O784.9 (3)O6B—S2—O8B115.5 (8)
C1—Sn1—O791.7 (3)O6B—S2—O7B111.7 (5)
C2—Sn1—O792.6 (3)O8B—S2—O7B107.9 (5)
O1—Sn1—O7172.44 (8)O6B—S2—O5B112.7 (4)
C1B—Sn1B—C2B120.5 (10)O8B—S2—O5B103.8 (6)
C1B—Sn1B—C3B124.0 (11)O7B—S2—O5B104.4 (3)
C2B—Sn1B—C3B115.4 (9)S1—O1—Sn1135.22 (9)
C1B—Sn1B—O7B84.5 (10)S1—O1—Sn1B127.57 (10)
C2B—Sn1B—O7B95.1 (9)S1—O2—Sn2Biii137.17 (12)
C3B—Sn1B—O7B94.1 (9)S1—O2—Sn2iii130.78 (9)
C1B—Sn1B—O192.9 (10)S1—O4—Sn3ii135.28 (10)
C2B—Sn1B—O191.7 (9)S1—O4—Sn3Bii126.92 (12)
C3B—Sn1B—O182.0 (9)S2—O5—Sn3141.14 (17)
O7B—Sn1B—O1173.07 (18)S2—O7—Sn1135.08 (14)
Sn1B—C1B—H1D109.5S2—O8—Sn2130.8 (3)
Sn1B—C1B—H1E109.5S2—O5B—Sn3B139.4 (3)
H1D—C1B—H1E109.5S2—O7B—Sn1B132.8 (3)
Sn1B—C1B—H1F109.5S2—O8B—Sn2B135.0 (9)
H1D—C1B—H1F109.5C10—C11—C12111.4 (13)
H1E—C1B—H1F109.5C10—C11—H11A109.4
Sn1B—C2B—H2D109.5C12—C11—H11A109.4
Sn1B—C2B—H2E109.5C10—C11—H11B109.4
H2D—C2B—H2E109.5C12—C11—H11B109.4
Sn1B—C2B—H2F109.5H11A—C11—H11B108.0
H2D—C2B—H2F109.5C13—C12—C11113.2 (12)
H2E—C2B—H2F109.5C13—C12—H12A108.9
Sn1B—C3B—H3D109.5C11—C12—H12A108.9
Sn1B—C3B—H3E109.5C13—C12—H12B108.9
H3D—C3B—H3E109.5C11—C12—H12B108.9
Sn1B—C3B—H3F109.5H12A—C12—H12B107.7
H3D—C3B—H3F109.5C12—C13—N1109.4 (9)
H3E—C3B—H3F109.5C12—C13—H13A109.8
C5—Sn2—C4120.6 (4)N1—C13—H13A109.8
C5—Sn2—C6119.1 (4)C12—C13—H13B109.8
C4—Sn2—C6120.3 (4)N1—C13—H13B109.8
C5—Sn2—O889.4 (5)H13A—C13—H13B108.2
C4—Sn2—O893.6 (4)C14—N1—C13107.9 (8)
C6—Sn2—O886.3 (5)C14—N1—H1G112.0
C5—Sn2—O2i93.6 (5)C13—N1—H1G108.5
C4—Sn2—O2i83.5 (4)C14—N1—H1H109.7
C6—Sn2—O2i93.6 (5)C13—N1—H1H111.0
O8—Sn2—O2i176.59 (11)H1G—N1—H1H107.8
C4B—Sn2B—C5B121.5 (12)N1—C14—C15112.7 (8)
C4B—Sn2B—C6B121.1 (12)N1—C14—H14A109.0
C5B—Sn2B—C6B117.3 (12)C15—C14—H14A109.0
C4B—Sn2B—O2i92.1 (12)N1—C14—H14B109.0
C5B—Sn2B—O2i89.1 (14)C15—C14—H14B109.0
C6B—Sn2B—O2i90.8 (14)H14A—C14—H14B107.8
C4B—Sn2B—O8B85.4 (13)C14—C15—C16113.1 (8)
C5B—Sn2B—O8B96.0 (14)C14—C15—H15A109.0
C6B—Sn2B—O8B86.7 (15)C16—C15—H15A109.0
O2i—Sn2B—O8B174.8 (4)C14—C15—H15B109.0
Sn2B—C4B—H4D109.5C16—C15—H15B109.0
Sn2B—C4B—H4E109.5H15A—C15—H15B107.8
H4D—C4B—H4E109.5C17—C16—C15114.1 (9)
Sn2B—C4B—H4F109.5C17—C16—H16A108.7
H4D—C4B—H4F109.5C15—C16—H16A108.7
H4E—C4B—H4F109.5C17—C16—H16B108.7
Sn2B—C5B—H5D109.5C15—C16—H16B108.7
Sn2B—C5B—H5E109.5H16A—C16—H16B107.6
H5D—C5B—H5E109.5C11B—C10B—H10D109.5
Sn2B—C5B—H5F109.5C11B—C10B—H10E109.5
H5D—C5B—H5F109.5H10D—C10B—H10E109.5
H5E—C5B—H5F109.5C11B—C10B—H10F109.5
Sn2B—C6B—H6D109.5H10D—C10B—H10F109.5
Sn2B—C6B—H6E109.5H10E—C10B—H10F109.5
H6D—C6B—H6E109.5C10B—C11B—C12B114.3 (13)
Sn2B—C6B—H6F109.5C10B—C11B—H11C108.7
H6D—C6B—H6F109.5C12B—C11B—H11C108.7
H6E—C6B—H6F109.5C10B—C11B—H11D108.7
C7—Sn3—C8115.2 (4)C12B—C11B—H11D108.7
C7—Sn3—C9120.4 (3)H11C—C11B—H11D107.6
C8—Sn3—C9124.4 (3)C11B—C12B—C13B111.6 (13)
C7—Sn3—O4ii85.7 (2)C11B—C12B—H12C109.3
C8—Sn3—O4ii94.8 (2)C13B—C12B—H12C109.3
C9—Sn3—O4ii90.7 (3)C11B—C12B—H12D109.3
C7—Sn3—O582.9 (2)C13B—C12B—H12D109.3
C8—Sn3—O590.4 (2)H12C—C12B—H12D108.0
C9—Sn3—O594.7 (3)N1B—C13B—C12B115.6 (11)
O4ii—Sn3—O5168.64 (10)N1B—C13B—H13C108.4
C8B—Sn3B—C7B116.0 (11)C12B—C13B—H13C108.4
C8B—Sn3B—C9B127.8 (10)N1B—C13B—H13D108.4
C7B—Sn3B—C9B116.1 (9)C12B—C13B—H13D108.4
C8B—Sn3B—O5B83.2 (8)H13C—C13B—H13D107.4
C7B—Sn3B—O5B90.6 (6)C14B—N1B—C13B120.3 (10)
C9B—Sn3B—O5B93.7 (8)C14B—N1B—H1I105.4
C8B—Sn3B—O4ii96.2 (8)C13B—N1B—H1I109.0
C7B—Sn3B—O4ii85.9 (6)C14B—N1B—H1J107.5
C9B—Sn3B—O4ii90.0 (8)C13B—N1B—H1J106.3
O5B—Sn3B—O4ii175.8 (2)H1I—N1B—H1J107.8
Sn3B—C7B—H7D109.5N1B—C14B—C15B112.0 (9)
Sn3B—C7B—H7E109.5N1B—C14B—H14C109.2
H7D—C7B—H7E109.5C15B—C14B—H14C109.2
Sn3B—C7B—H7F109.5N1B—C14B—H14D109.2
H7D—C7B—H7F109.5C15B—C14B—H14D109.2
H7E—C7B—H7F109.5H14C—C14B—H14D107.9
Sn3B—C8B—H8D109.5C14B—C15B—C16B108.9 (9)
Sn3B—C8B—H8E109.5C14B—C15B—H15C109.9
H8D—C8B—H8E109.5C16B—C15B—H15C109.9
Sn3B—C8B—H8F109.5C14B—C15B—H15D109.9
H8D—C8B—H8F109.5C16B—C15B—H15D109.9
H8E—C8B—H8F109.5H15C—C15B—H15D108.3
Sn3B—C9B—H9D109.5C17B—C16B—C15B114.5 (10)
Sn3B—C9B—H9E109.5C17B—C16B—H16C108.6
H9D—C9B—H9E109.5C15B—C16B—H16C108.6
Sn3B—C9B—H9F109.5C17B—C16B—H16D108.6
H9D—C9B—H9F109.5C15B—C16B—H16D108.6
H9E—C9B—H9F109.5H16C—C16B—H16D107.6
O3—S1—O1111.15 (10)C16B—C17B—H17D109.5
O3—S1—O2110.76 (9)C16B—C17B—H17E109.5
O1—S1—O2107.90 (9)H17D—C17B—H17E109.5
O3—S1—O4108.77 (9)C16B—C17B—H17F109.5
O1—S1—O4108.76 (9)H17D—C17B—H17F109.5
O2—S1—O4109.45 (9)H17E—C17B—H17F109.5
O3—S1—O1—Sn1106.91 (14)O7—S2—O8—Sn2153.4 (3)
O2—S1—O1—Sn114.72 (16)O5—S2—O8—Sn284.2 (4)
O4—S1—O1—Sn1133.36 (13)O6—S2—O8—Sn233.3 (4)
O3—S1—O1—Sn1B103.90 (14)O8B—S2—O8—Sn263 (2)
O2—S1—O1—Sn1B17.73 (16)O7B—S2—O8—Sn2127.2 (4)
O4—S1—O1—Sn1B136.37 (13)O5B—S2—O8—Sn2128.2 (4)
C3—Sn1—O1—S1173.5 (3)C5—Sn2—O8—S272.3 (5)
C1—Sn1—O1—S149.9 (3)C4—Sn2—O8—S248.3 (5)
C2—Sn1—O1—S167.8 (2)C6—Sn2—O8—S2168.5 (5)
C3—Sn1—O1—Sn1B156.0 (6)O6B—S2—O5B—Sn3B95.0 (7)
C1—Sn1—O1—Sn1B32.5 (6)O7—S2—O5B—Sn3B154.8 (6)
C2—Sn1—O1—Sn1B85.3 (6)O8—S2—O5B—Sn3B50.1 (6)
C1B—Sn1B—O1—S152.2 (9)O5—S2—O5B—Sn3B43.9 (4)
C2B—Sn1B—O1—S168.5 (6)O6—S2—O5B—Sn3B106.0 (5)
C3B—Sn1B—O1—S1176.1 (8)O8B—S2—O5B—Sn3B30.6 (7)
C1B—Sn1B—O1—Sn1143.3 (10)O7B—S2—O5B—Sn3B143.5 (5)
C2B—Sn1B—O1—Sn196.1 (8)C8B—Sn3B—O5B—S2177.8 (10)
C3B—Sn1B—O1—Sn119.3 (9)C7B—Sn3B—O5B—S266.1 (10)
O3—S1—O2—Sn2Biii46.6 (2)C9B—Sn3B—O5B—S250.2 (8)
O1—S1—O2—Sn2Biii168.50 (19)O6B—S2—O7B—Sn1B164.8 (7)
O4—S1—O2—Sn2Biii73.3 (2)O7—S2—O7B—Sn1B62.0 (5)
O3—S1—O2—Sn2iii44.60 (15)O8—S2—O7B—Sn1B70.9 (5)
O1—S1—O2—Sn2iii166.47 (11)O5—S2—O7B—Sn1B51.2 (8)
O4—S1—O2—Sn2iii75.33 (13)O6—S2—O7B—Sn1B179.2 (5)
O3—S1—O4—Sn3ii165.74 (13)O8B—S2—O7B—Sn1B67.2 (8)
O1—S1—O4—Sn3ii44.55 (16)O5B—S2—O7B—Sn1B42.8 (6)
O2—S1—O4—Sn3ii73.12 (15)C1B—Sn1B—O7B—S2148.8 (10)
O3—S1—O4—Sn3Bii171.41 (16)C2B—Sn1B—O7B—S228.6 (8)
O1—S1—O4—Sn3Bii50.21 (18)C3B—Sn1B—O7B—S287.4 (10)
O2—S1—O4—Sn3Bii67.45 (17)O6B—S2—O8B—Sn2B27.1 (11)
O6B—S2—O5—Sn3178.2 (6)O7—S2—O8B—Sn2B131.5 (7)
O7—S2—O5—Sn367.0 (3)O8—S2—O8B—Sn2B88 (2)
O8—S2—O5—Sn355.3 (4)O5—S2—O8B—Sn2B111.9 (8)
O6—S2—O5—Sn3174.7 (3)O6—S2—O8B—Sn2B3.6 (10)
O8B—S2—O5—Sn362.7 (6)O7B—S2—O8B—Sn2B98.7 (9)
O7B—S2—O5—Sn360.5 (5)O5B—S2—O8B—Sn2B151.0 (8)
O5B—S2—O5—Sn347.9 (3)C4B—Sn2B—O8B—S282.5 (13)
C7—Sn3—O5—S2166.7 (4)C5B—Sn2B—O8B—S238.8 (13)
C8—Sn3—O5—S278.0 (4)C6B—Sn2B—O8B—S2155.9 (13)
C9—Sn3—O5—S246.6 (3)C10—C11—C12—C13179 (2)
O4ii—Sn3—O5—S2164.7 (4)C11—C12—C13—N1174.2 (18)
O6B—S2—O7—Sn1153.6 (5)C12—C13—N1—C14166.7 (16)
O8—S2—O7—Sn110.0 (4)C13—N1—C14—C15179.4 (13)
O5—S2—O7—Sn1112.2 (3)N1—C14—C15—C16172.4 (13)
O6—S2—O7—Sn1130.7 (3)C14—C15—C16—C17179.6 (11)
O8B—S2—O7—Sn15.2 (7)C10B—C11B—C12B—C13B178 (2)
O7B—S2—O7—Sn161.2 (4)C11B—C12B—C13B—N1B178 (2)
O5B—S2—O7—Sn199.2 (3)C12B—C13B—N1B—C14B178.6 (18)
C3—Sn1—O7—S2156.8 (4)C13B—N1B—C14B—C15B176.8 (16)
C1—Sn1—O7—S279.6 (4)N1B—C14B—C15B—C16B176.8 (13)
C2—Sn1—O7—S238.2 (3)C14B—C15B—C16B—C17B71.4 (16)
O6B—S2—O8—Sn213.0 (6)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y+1, z+1; (iii) x, y+3/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1H···O60.921.882.785 (16)168
N1B—H1J···O6B0.922.112.98 (2)159
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1H···O60.921.882.785 (16)167.7
N1B—H1J···O6B0.922.112.98 (2)159.3
Acknowledgements top

We thank Dr Mohamedally Kurmoo, Laboratoire Decomet, CNRS-UMR 7177 Université de Strasbourg, 4 rue Blaize Pascal CS 90032, 67081 Strasbourg Cedex, France, for access to the X-ray diffraction equipment.

references
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