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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2013 May 15;69(Pt 6):m316. doi: 10.1107/S1600536813012300

(O-Methyl di­thio­carbonato-κS)tri­phenyl­tin(IV)

Fatima Javed a, Saqib Ali a, Wajid Shah b, M Nawaz Tahir c,*, Hameed Ullah d
PMCID: PMC3684880  PMID: 23794982

Abstract

In the title compound, [Sn(C6H5)3(C2H3OS2)], the SnIV atom adopts a distorted SnC3S tetra­hedral coordination geometry. A short Sn⋯O contact [2.988 (4) Å] is also present. The phenyl rings are each disordered over two sets of sites with an occupancy ratio of 0.550 (8):0.450 (8). The crystal studied was found to be a racemic twin with a twin component ratio of 0.57 (18):0.43 (18).

Related literature  

For a related structure, see: Ng & Rae (2000 ▶).graphic file with name e-69-0m316-scheme1.jpg

Experimental  

Crystal data  

  • [Sn(C6H5)3(C2H3OS2)]

  • M r = 457.15

  • Monoclinic, Inline graphic

  • a = 17.4400 (9) Å

  • b = 8.4734 (4) Å

  • c = 15.6069 (9) Å

  • β = 119.626 (2)°

  • V = 2004.82 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.49 mm−1

  • T = 296 K

  • 0.28 × 0.22 × 0.18 mm

Data collection  

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.683, T max = 0.763

  • 7166 measured reflections

  • 3483 independent reflections

  • 3341 reflections with I > 2σ(I)

  • R int = 0.014

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.022

  • wR(F 2) = 0.055

  • S = 1.04

  • 3483 reflections

  • 112 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.29 e Å−3

  • Absolute structure: Flack (1983 ▶), 1387 Friedel pairs

  • Flack parameter: 0.43 (18)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON.

Supplementary Material

Click here for additional data file. (36.7KB, cif)

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012300/hb7077sup1.cif

e-69-0m316-sup1.cif (36.7KB, cif)
Click here for additional data file. (167.4KB, hkl)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012300/hb7077Isup2.hkl

e-69-0m316-Isup2.hkl (167.4KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

supplementary crystallographic information

Comment

The crystal structure of (O-methyl dithiocarbonato-S)-triphenyl-tin(iv) (Ng & Rae, 2000) has been reported, which is related to title compound (I).

In (I) the coordination around tin atom is distorted tetrahedral with three C-atoms and an S-atom. The tin and coordinated sulpher atom is at a distance of -0.5497 (47) Å and -2.9805 (53) Å from the plane (C3A/C9A/C15A). The phenyl rings are disordered over two sites with occupancy ratio of 0.550 (8):0.450 (8). The dihedral angle between disordered rings (C3A–C8A)/(C3B–C8B), (C9A–C14A)/(C9B–C14B) and (C15A–C20A)/(C15B–C20B) is 19.2 (7)°, 8.3 (10)° and 14.1 (5)°, respectively. The O-methyl hydrogen carbonodithioate moiety (S1/C1/S2/O1/C2) is planar with r. m. s. deviation of 0.0326 Å and is oriented at a dihedral angle of 71.22 (19)° with the plane (C3A/C9A/C15A).

Experimental

Potassium-O-methyl carrbonodithioate (10 mmol, 1.46 g) was dissolved in methanol and stirred for 30 min. Then triphenytin(IV) chloride was added dropwise and the reaction mixture was stirred for 7–8 h till white precipitates were appeared. The resultant mixture was filtered to remove KCl salt. The filtrate was rotary evaporated to get white solid mass and recrystalized from chloroform to obtaine colourless prisms of (I) in 85.33% yield.

Refinement

There is a recamic twin with BASF value of 0.43147.

The benzene rings of triphenyl tin are disordered over two sites with occupancy ratio of 0.550 (8):0.450 (8) and were idealized as regular hexagons with C–C bond distance equal to 1.39 Å. The C-atoms of respective rings were treated as anisotropic with equal thermal parameters.

The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for other H-atoms.

Figures

Fig. 1.

Fig. 1.

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View of the title compound with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. Only the major part of atoms of disordered group are shown for clarity.

Crystal data

[Sn(C6H5)3(C2H3OS2)] F(000) = 912
Mr = 457.15 Dx = 1.515 Mg m−3
Monoclinic, Cc Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc Cell parameters from 3341 reflections
a = 17.4400 (9) Å θ = 2.8–26.0°
b = 8.4734 (4) Å µ = 1.49 mm−1
c = 15.6069 (9) Å T = 296 K
β = 119.626 (2)° Prism, white
V = 2004.82 (19) Å3 0.28 × 0.22 × 0.18 mm
Z = 4
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Data collection

Bruker Kappa APEXII CCD diffractometer 3483 independent reflections
Radiation source: fine-focus sealed tube 3341 reflections with I > 2σ(I)
Graphite monochromator Rint = 0.014
Detector resolution: 8.00 pixels mm-1 θmax = 26.0°, θmin = 2.8°
ω scans h = −21→20
Absorption correction: multi-scan (SADABS; Bruker, 2005) k = −10→10
Tmin = 0.683, Tmax = 0.763 l = −19→19
7166 measured reflections
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Refinement

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)] = 0.022 H-atom parameters constrained
wR(F2) = 0.055 w = 1/[σ2(Fo2) + (0.0246P)2 + 2.1104P] where P = (Fo2 + 2Fc2)/3
S = 1.04 (Δ/σ)max < 0.001
3483 reflections Δρmax = 0.44 e Å−3
112 parameters Δρmin = −0.29 e Å−3
2 restraints Absolute structure: Flack (1983), 1387 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: 0.43 (18)
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Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement 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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
Sn1 0.01045 (1) 0.18518 (2) 0.25080 (1) 0.0459 (1)
S1 −0.10922 (8) 0.30516 (13) 0.10239 (9) 0.0611 (4)
S2 −0.11228 (15) 0.6208 (2) 0.02348 (15) 0.1128 (7)
O1 0.0289 (2) 0.4577 (4) 0.1408 (3) 0.0687 (11)
C1 −0.0567 (3) 0.4711 (5) 0.0901 (3) 0.0581 (14)
C2 0.0828 (4) 0.5909 (7) 0.1467 (5) 0.106 (3)
C3A 0.0722 (5) 0.3677 (6) 0.3576 (5) 0.0589 (8) 0.550 (8)
C4A 0.1594 (5) 0.3461 (6) 0.4305 (5) 0.0589 (8) 0.550 (8)
C5A 0.2039 (4) 0.4656 (8) 0.4982 (5) 0.0589 (8) 0.550 (8)
C6A 0.1611 (4) 0.6067 (6) 0.4930 (4) 0.0589 (8) 0.550 (8)
C7A 0.0738 (4) 0.6283 (6) 0.4200 (5) 0.0589 (8) 0.550 (8)
C8A 0.0294 (4) 0.5088 (8) 0.3523 (5) 0.0589 (8) 0.550 (8)
C9A −0.0659 (5) 0.0278 (10) 0.2859 (7) 0.0590 (9) 0.550 (8)
C10A −0.0786 (6) 0.0702 (8) 0.3640 (6) 0.0590 (9) 0.550 (8)
C11A −0.1305 (5) −0.0234 (8) 0.3883 (5) 0.0590 (9) 0.550 (8)
C12A −0.1697 (4) −0.1594 (7) 0.3345 (5) 0.0590 (9) 0.550 (8)
C13A −0.1570 (4) −0.2018 (7) 0.2564 (5) 0.0590 (9) 0.550 (8)
C14A −0.1051 (5) −0.1081 (10) 0.2320 (6) 0.0590 (9) 0.550 (8)
C15A 0.0947 (4) 0.0647 (8) 0.2102 (5) 0.0576 (8) 0.550 (8)
C16A 0.0687 (3) 0.0619 (8) 0.1104 (5) 0.0576 (8) 0.550 (8)
C17A 0.1207 (4) −0.0140 (7) 0.0785 (4) 0.0576 (8) 0.550 (8)
C18A 0.1987 (3) −0.0872 (7) 0.1464 (5) 0.0576 (8) 0.550 (8)
C19A 0.2247 (3) −0.0844 (8) 0.2462 (4) 0.0576 (8) 0.550 (8)
C20A 0.1727 (4) −0.0084 (8) 0.2780 (4) 0.0576 (8) 0.550 (8)
C16B 0.0959 (5) 0.0687 (10) 0.1263 (6) 0.0576 (8) 0.450 (8)
C17B 0.1575 (6) −0.0144 (9) 0.1123 (6) 0.0576 (8) 0.450 (8)
C18B 0.2203 (5) −0.1074 (9) 0.1878 (7) 0.0576 (8) 0.450 (8)
C19B 0.2215 (4) −0.1172 (9) 0.2773 (6) 0.0576 (8) 0.450 (8)
C20B 0.1598 (5) −0.0341 (10) 0.2913 (5) 0.0576 (8) 0.450 (8)
C5B 0.1948 (4) 0.5125 (9) 0.4774 (7) 0.0589 (8) 0.450 (8)
C6B 0.1388 (5) 0.6235 (7) 0.4831 (6) 0.0589 (8) 0.450 (8)
C7B 0.0479 (5) 0.6058 (9) 0.4259 (6) 0.0589 (8) 0.450 (8)
C8B 0.0130 (4) 0.4772 (10) 0.3630 (7) 0.0589 (8) 0.450 (8)
C9B −0.0674 (6) 0.0296 (11) 0.2813 (9) 0.0590 (9) 0.450 (8)
C10B −0.0998 (6) 0.0581 (9) 0.3453 (7) 0.0590 (9) 0.450 (8)
C11B −0.1561 (5) −0.0502 (9) 0.3528 (6) 0.0590 (9) 0.450 (8)
C12B −0.1800 (5) −0.1870 (8) 0.2963 (6) 0.0590 (9) 0.450 (8)
C13B −0.1476 (6) −0.2155 (9) 0.2323 (6) 0.0590 (9) 0.450 (8)
C14B −0.0913 (7) −0.1072 (12) 0.2248 (8) 0.0590 (9) 0.450 (8)
C15B 0.0970 (5) 0.0588 (10) 0.2158 (7) 0.0576 (8) 0.450 (8)
C4B 0.1599 (6) 0.3839 (8) 0.4144 (7) 0.0589 (8) 0.450 (8)
C3B 0.0690 (6) 0.3662 (8) 0.3572 (6) 0.0589 (8) 0.450 (8)
H20A 0.19005 −0.00656 0.34478 0.0691* 0.550 (8)
H19A 0.27690 −0.13333 0.29154 0.0691* 0.550 (8)
H6A 0.19081 0.68660 0.53825 0.0706* 0.550 (8)
H7A 0.04520 0.72266 0.41647 0.0706* 0.550 (8)
H8A −0.02897 0.52327 0.30348 0.0706* 0.550 (8)
H10A −0.05241 0.16116 0.39997 0.0708* 0.550 (8)
H11A −0.13903 0.00491 0.44055 0.0708* 0.550 (8)
H12A −0.20441 −0.22204 0.35075 0.0708* 0.550 (8)
H13A −0.18317 −0.29273 0.22036 0.0708* 0.550 (8)
H14A −0.09654 −0.13648 0.17978 0.0708* 0.550 (8)
H16A 0.01651 0.11088 0.06504 0.0691* 0.550 (8)
H17A 0.10335 −0.01589 0.01181 0.0691* 0.550 (8)
H18A 0.23355 −0.13799 0.12506 0.0691* 0.550 (8)
H2A 0.07169 0.61782 0.08181 0.1596*
H2B 0.14393 0.56420 0.18742 0.1596*
H2C 0.06866 0.67927 0.17483 0.1596*
H4A 0.18807 0.25175 0.43404 0.0706* 0.550 (8)
H5A 0.26224 0.45114 0.54703 0.0706* 0.550 (8)
H4B 0.19733 0.30958 0.41060 0.0706* 0.450 (8)
H5B 0.25556 0.52423 0.51568 0.0706* 0.450 (8)
H6B 0.16213 0.70949 0.52526 0.0706* 0.450 (8)
H7B 0.01046 0.68010 0.42975 0.0706* 0.450 (8)
H8B −0.04778 0.46545 0.32467 0.0706* 0.450 (8)
H10B −0.08378 0.14963 0.38313 0.0708* 0.450 (8)
H11B −0.17772 −0.03112 0.39561 0.0708* 0.450 (8)
H12B −0.21762 −0.25945 0.30127 0.0708* 0.450 (8)
H13B −0.16359 −0.30704 0.19445 0.0708* 0.450 (8)
H14B −0.06966 −0.12630 0.18198 0.0708* 0.450 (8)
H16B 0.05384 0.13082 0.07576 0.0691* 0.450 (8)
H17B 0.15674 −0.00783 0.05235 0.0691* 0.450 (8)
H18B 0.26155 −0.16294 0.17837 0.0691* 0.450 (8)
H19B 0.26346 −0.17939 0.32780 0.0691* 0.450 (8)
H20B 0.16056 −0.04074 0.35121 0.0691* 0.450 (8)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Sn1 0.0445 (1) 0.0449 (1) 0.0519 (1) −0.0026 (2) 0.0266 (1) −0.0031 (2)
S1 0.0473 (6) 0.0687 (7) 0.0598 (7) −0.0047 (5) 0.0208 (5) 0.0035 (5)
S2 0.1330 (16) 0.0839 (10) 0.0928 (11) 0.0212 (10) 0.0338 (11) 0.0371 (9)
O1 0.071 (2) 0.0609 (18) 0.078 (2) −0.0144 (15) 0.0398 (18) 0.0013 (15)
C1 0.074 (3) 0.052 (2) 0.050 (2) 0.000 (2) 0.032 (2) −0.0010 (17)
C2 0.104 (4) 0.085 (4) 0.144 (5) −0.036 (3) 0.072 (4) −0.005 (4)
C3A 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
C4A 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
C5A 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
C6A 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
C7A 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
C8A 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
C9A 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C10A 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C11A 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C12A 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C13A 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C14A 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C15A 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C16A 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C17A 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C18A 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C19A 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C20A 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C16B 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C17B 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C18B 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C19B 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C20B 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C5B 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
C6B 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
C7B 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
C8B 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
C9B 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C10B 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C11B 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C12B 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C13B 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C14B 0.0570 (14) 0.0649 (12) 0.0597 (18) −0.0151 (10) 0.0324 (12) −0.0040 (11)
C15B 0.0493 (13) 0.0652 (13) 0.0660 (17) −0.0020 (11) 0.0344 (13) −0.0058 (12)
C4B 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
C3B 0.0513 (14) 0.0497 (13) 0.0659 (14) 0.0040 (10) 0.0216 (12) −0.0055 (10)
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Geometric parameters (Å, º)

Sn1—S1 2.4444 (13) C16B—C17B 1.389 (14)
Sn1—C3A 2.134 (6) C17A—C18A 1.390 (9)
Sn1—C9A 2.138 (10) C17B—C18B 1.390 (12)
Sn1—C15A 2.127 (8) C18A—C19A 1.391 (9)
Sn1—C3B 2.116 (8) C18B—C19B 1.389 (13)
Sn1—C9B 2.109 (11) C19A—C20A 1.389 (10)
Sn1—C15B 2.130 (10) C19B—C20B 1.391 (12)
S1—C1 1.740 (5) C2—H2A 0.9600
S2—C1 1.623 (5) C2—H2B 0.9600
O1—C1 1.304 (7) C2—H2C 0.9600
O1—C2 1.442 (8) C4A—H4A 0.9300
C3A—C4A 1.389 (12) C4B—H4B 0.9300
C3A—C8A 1.390 (10) C5A—H5A 0.9300
C3B—C4B 1.391 (15) C5B—H5B 0.9300
C3B—C8B 1.391 (13) C6A—H6A 0.9300
C4A—C5A 1.390 (9) C6B—H6B 0.9300
C4B—C5B 1.390 (12) C7A—H7A 0.9300
C5A—C6A 1.390 (9) C7B—H7B 0.9300
C5B—C6B 1.390 (12) C8A—H8A 0.9300
C6A—C7A 1.391 (10) C8B—H8B 0.9300
C6B—C7B 1.391 (13) C10A—H10A 0.9300
C7A—C8A 1.390 (9) C10B—H10B 0.9300
C7B—C8B 1.390 (12) C11A—H11A 0.9300
C9A—C14A 1.390 (12) C11B—H11B 0.9300
C9A—C10A 1.390 (13) C12A—H12A 0.9300
C9B—C14B 1.390 (15) C12B—H12B 0.9300
C9B—C10B 1.390 (16) C13A—H13A 0.9300
C10A—C11A 1.390 (13) C13B—H13B 0.9300
C10B—C11B 1.391 (14) C14A—H14A 0.9300
C11A—C12A 1.390 (9) C14B—H14B 0.9300
C11B—C12B 1.390 (11) C16A—H16A 0.9300
C12A—C13A 1.390 (10) C16B—H16B 0.9300
C12B—C13B 1.390 (14) C17A—H17A 0.9300
C13A—C14A 1.391 (12) C17B—H17B 0.9300
C13B—C14B 1.391 (16) C18A—H18A 0.9300
C15A—C16A 1.391 (10) C18B—H18B 0.9300
C15A—C20A 1.390 (10) C19A—H19A 0.9300
C15B—C20B 1.390 (12) C19B—H19B 0.9300
C15B—C16B 1.390 (13) C20A—H20A 0.9300
C16A—C17A 1.389 (10) C20B—H20B 0.9300
S1—Sn1—C3A 107.67 (18) O1—C2—H2B 109.00
S1—Sn1—C9A 98.9 (3) O1—C2—H2C 109.00
S1—Sn1—C15A 108.02 (19) H2A—C2—H2B 109.00
S1—Sn1—C3B 107.3 (2) H2A—C2—H2C 109.00
S1—Sn1—C9B 97.5 (3) H2B—C2—H2C 109.00
S1—Sn1—C15B 110.3 (3) C3A—C4A—H4A 120.00
C3A—Sn1—C9A 112.9 (3) C5A—C4A—H4A 120.00
C3A—Sn1—C15A 115.1 (3) C5B—C4B—H4B 120.00
C9A—Sn1—C15A 112.7 (3) C3B—C4B—H4B 120.00
C3B—Sn1—C9B 113.0 (4) C6A—C5A—H5A 120.00
C3B—Sn1—C15B 115.9 (4) C4A—C5A—H5A 120.00
C9B—Sn1—C15B 111.1 (4) C6B—C5B—H5B 120.00
Sn1—S1—C1 101.02 (16) C4B—C5B—H5B 120.00
C1—O1—C2 119.0 (4) C7A—C6A—H6A 120.00
S1—C1—S2 121.5 (3) C5A—C6A—H6A 120.00
S1—C1—O1 111.7 (3) C7B—C6B—H6B 120.00
S2—C1—O1 126.8 (4) C5B—C6B—H6B 120.00
Sn1—C3A—C4A 118.0 (4) C8A—C7A—H7A 120.00
Sn1—C3A—C8A 121.9 (6) C6A—C7A—H7A 120.00
C4A—C3A—C8A 120.0 (6) C6B—C7B—H7B 120.00
Sn1—C3B—C8B 117.4 (7) C8B—C7B—H7B 120.00
C4B—C3B—C8B 120.0 (7) C7A—C8A—H8A 120.00
Sn1—C3B—C4B 122.5 (7) C3A—C8A—H8A 120.00
C3A—C4A—C5A 120.0 (6) C7B—C8B—H8B 120.00
C3B—C4B—C5B 120.0 (9) C3B—C8B—H8B 120.00
C4A—C5A—C6A 120.0 (7) C11A—C10A—H10A 120.00
C4B—C5B—C6B 120.0 (9) C9A—C10A—H10A 120.00
C5A—C6A—C7A 120.0 (5) C11B—C10B—H10B 120.00
C5B—C6B—C7B 120.0 (7) C9B—C10B—H10B 120.00
C6A—C7A—C8A 120.0 (6) C12A—C11A—H11A 120.00
C6B—C7B—C8B 120.0 (8) C10A—C11A—H11A 120.00
C3A—C8A—C7A 120.0 (7) C12B—C11B—H11B 120.00
C3B—C8B—C7B 120.0 (8) C10B—C11B—H11B 120.00
Sn1—C9A—C10A 116.9 (6) C11A—C12A—H12A 120.00
Sn1—C9A—C14A 122.9 (7) C13A—C12A—H12A 120.00
C10A—C9A—C14A 120.1 (9) C11B—C12B—H12B 120.00
C10B—C9B—C14B 120.0 (10) C13B—C12B—H12B 120.00
Sn1—C9B—C10B 126.1 (7) C14A—C13A—H13A 120.00
Sn1—C9B—C14B 113.8 (9) C12A—C13A—H13A 120.00
C9A—C10A—C11A 120.0 (7) C14B—C13B—H13B 120.00
C9B—C10B—C11B 120.0 (8) C12B—C13B—H13B 120.00
C10A—C11A—C12A 120.0 (7) C13A—C14A—H14A 120.00
C10B—C11B—C12B 120.0 (9) C9A—C14A—H14A 120.00
C11A—C12A—C13A 120.0 (7) C13B—C14B—H14B 120.00
C11B—C12B—C13B 120.0 (8) C9B—C14B—H14B 120.00
C12A—C13A—C14A 120.0 (6) C17A—C16A—H16A 120.00
C12B—C13B—C14B 120.0 (8) C15A—C16A—H16A 120.00
C9A—C14A—C13A 119.9 (8) C17B—C16B—H16B 120.00
C9B—C14B—C13B 120.0 (11) C15B—C16B—H16B 120.00
Sn1—C15A—C16A 116.8 (5) C16A—C17A—H17A 120.00
C16A—C15A—C20A 120.0 (7) C18A—C17A—H17A 120.00
Sn1—C15A—C20A 123.2 (5) C18B—C17B—H17B 120.00
Sn1—C15B—C20B 115.4 (7) C16B—C17B—H17B 120.00
C16B—C15B—C20B 120.0 (9) C19A—C18A—H18A 120.00
Sn1—C15B—C16B 124.6 (7) C17A—C18A—H18A 120.00
C15A—C16A—C17A 120.0 (6) C19B—C18B—H18B 120.00
C15B—C16B—C17B 120.0 (8) C17B—C18B—H18B 120.00
C16A—C17A—C18A 120.0 (6) C20A—C19A—H19A 120.00
C16B—C17B—C18B 120.0 (8) C18A—C19A—H19A 120.00
C17A—C18A—C19A 120.0 (6) C20B—C19B—H19B 120.00
C17B—C18B—C19B 120.0 (9) C18B—C19B—H19B 120.00
C18A—C19A—C20A 120.0 (6) C19A—C20A—H20A 120.00
C18B—C19B—C20B 120.0 (7) C15A—C20A—H20A 120.00
C15A—C20A—C19A 120.1 (5) C15B—C20B—H20B 120.00
C15B—C20B—C19B 120.0 (8) C19B—C20B—H20B 120.00
O1—C2—H2A 109.00
C3A—Sn1—S1—C1 46.2 (3) Sn1—C3A—C4A—C5A 176.3 (6)
C9A—Sn1—S1—C1 163.8 (3) C8A—C3A—C4A—C5A 0.0 (12)
C15A—Sn1—S1—C1 −78.7 (3) Sn1—C3A—C8A—C7A −176.2 (6)
S1—Sn1—C3A—C4A −155.3 (6) C4A—C3A—C8A—C7A −0.1 (12)
S1—Sn1—C3A—C8A 20.9 (7) C3A—C4A—C5A—C6A 0.1 (12)
C9A—Sn1—C3A—C4A 96.6 (7) C4A—C5A—C6A—C7A −0.1 (11)
C9A—Sn1—C3A—C8A −87.2 (7) C5A—C6A—C7A—C8A 0.0 (11)
C15A—Sn1—C3A—C4A −34.8 (7) C6A—C7A—C8A—C3A 0.1 (11)
C15A—Sn1—C3A—C8A 141.4 (6) Sn1—C9A—C10A—C11A 177.4 (6)
S1—Sn1—C9A—C10A −104.6 (7) C14A—C9A—C10A—C11A 0.0 (14)
S1—Sn1—C9A—C14A 72.7 (8) Sn1—C9A—C14A—C13A −177.3 (6)
C3A—Sn1—C9A—C10A 8.9 (8) C10A—C9A—C14A—C13A −0.1 (13)
C3A—Sn1—C9A—C14A −173.8 (7) C9A—C10A—C11A—C12A 0.0 (13)
C15A—Sn1—C9A—C10A 141.5 (7) C10A—C11A—C12A—C13A 0.0 (11)
C15A—Sn1—C9A—C14A −41.2 (9) C11A—C12A—C13A—C14A 0.0 (11)
S1—Sn1—C15A—C16A −3.9 (6) C12A—C13A—C14A—C9A 0.1 (12)
S1—Sn1—C15A—C20A 175.7 (5) Sn1—C15A—C16A—C17A 179.7 (5)
C3A—Sn1—C15A—C16A −124.3 (5) C20A—C15A—C16A—C17A 0.0 (10)
C3A—Sn1—C15A—C20A 55.4 (7) Sn1—C15A—C20A—C19A −179.7 (5)
C9A—Sn1—C15A—C16A 104.2 (6) C16A—C15A—C20A—C19A −0.1 (11)
C9A—Sn1—C15A—C20A −76.1 (7) C15A—C16A—C17A—C18A 0.0 (10)
Sn1—S1—C1—S2 −161.2 (3) C16A—C17A—C18A—C19A 0.0 (10)
Sn1—S1—C1—O1 18.0 (4) C17A—C18A—C19A—C20A 0.0 (10)
C2—O1—C1—S1 −174.0 (4) C18A—C19A—C20A—C15A 0.1 (10)
C2—O1—C1—S2 5.1 (7)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7077).

References

  1. Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  2. Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.
  4. Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  5. Ng, S. W. & Rae, A. D. (2000). Acta Cryst. C56, e47–e48.
  6. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  7. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Click here for additional data file. (36.7KB, cif)

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012300/hb7077sup1.cif

e-69-0m316-sup1.cif (36.7KB, cif)
Click here for additional data file. (167.4KB, hkl)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012300/hb7077Isup2.hkl

e-69-0m316-Isup2.hkl (167.4KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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