Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052804/hb2613sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052804/hb2613Isup2.hkl |
CCDC reference: 667255
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.007 Å
- R factor = 0.036
- wR factor = 0.077
- Data-to-parameter ratio = 20.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.51 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - O5 .. 5.12 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C28 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C36
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A solution of p-toluenesulfonic aicd (100 mmol) in water (20 ml) was added to a mixture of Ag2CO3 (50 mmol) in water (20 ml). After stirring for several minutes until no CO2 was given off, the white precipitate (AgL) was collected by removing the solvent in vacuo. Then a mixture of AgL (1.0 mmol) and Bz2SnCl2 (1.0 mmol) in CH2Cl2 (30 ml) were stirred continuously for 24 h at room temperature, the precipitate of AgCl was removed by filtration. Colourless blocks of (I) were obtained by evaporating the filtrate at room temperature.
The H atoms were positioned geometrically (C—H = 0.93–0.9and refined as riding atoms with C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate but not to tip.
Some organotin(IV) derivatives of sulfonates show antitumor activities (Chandrasekhar et al., 2003). In this paper, we report the structure of a new organotin sulfonate, [Sn4(Bz)8(L)2(OCH3)2(O)2], (I), where Bz = the benzyl group and L = p-toluenesulfonate.
Selected bond lengths for (I) are listed in Table 1. Both Sn(IV) atoms are five-coordinated in distorted trigonal–bipyramidal geometries. The exo tin atom (Sn1) is coordinated by two benzyl groups, one µ3-O2- anion, one µ2-OCH3- anion and one L O atom. The endo tin atom (Sn2) is coordinated by two benzyl groups, two µ3-O2- anions, one µ2-OCH3- anion and one L O atom. The four Sn(IV) atoms are connected by two µ3-O2- anions, generating the title Sn—O ladder structure. The p-toluenesulfonate anions and µ2-OCH3- anion are attached on both sides of the ladder.
For related literature, see: Chandrasekhar et al. (2003).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. View of (I) with displacement ellipsoids drawn at the 20% probability level and all H atoms omitted for clarity. Symmetry code: (i) 2 - x, 2 - y, 1 - z. |
[Sn4(C7H7)8(CH3O)2(C7H7O3S)2O2] | F(000) = 1640 |
Mr = 1640.21 | Dx = 1.617 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 7979 reflections |
a = 11.520 (5) Å | θ = 1.6–28.4° |
b = 11.302 (4) Å | µ = 1.59 mm−1 |
c = 26.219 (11) Å | T = 293 K |
β = 99.409 (1)° | Block, colourless |
V = 3368 (2) Å3 | 0.43 × 0.15 × 0.13 mm |
Z = 2 |
Bruker APEX CCD diffractometer | 5980 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
ω scans | θmax = 28.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.747, Tmax = 0.820 | k = −15→11 |
20431 measured reflections | l = −24→34 |
7979 independent reflections |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.029P)2 + 0.8649P] where P = (Fo2 + 2Fc2)/3 |
7979 reflections | (Δ/σ)max = 0.001 |
397 parameters | Δρmax = 0.74 e Å−3 |
0 restraints | Δρmin = −0.88 e Å−3 |
[Sn4(C7H7)8(CH3O)2(C7H7O3S)2O2] | V = 3368 (2) Å3 |
Mr = 1640.21 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.520 (5) Å | µ = 1.59 mm−1 |
b = 11.302 (4) Å | T = 293 K |
c = 26.219 (11) Å | 0.43 × 0.15 × 0.13 mm |
β = 99.409 (1)° |
Bruker APEX CCD diffractometer | 7979 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 5980 reflections with I > 2σ(I) |
Tmin = 0.747, Tmax = 0.820 | Rint = 0.033 |
20431 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.74 e Å−3 |
7979 reflections | Δρmin = −0.88 e Å−3 |
397 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6175 (4) | −0.1697 (5) | 0.5096 (2) | 0.0794 (15) | |
H1 | 0.5940 | −0.1384 | 0.5391 | 0.095* | |
C2 | 0.5355 (4) | −0.1953 (5) | 0.4674 (3) | 0.0826 (17) | |
H2 | 0.4560 | −0.1821 | 0.4679 | 0.099* | |
C3 | 0.5714 (4) | −0.2403 (4) | 0.4247 (2) | 0.0740 (15) | |
H3 | 0.5161 | −0.2578 | 0.3957 | 0.089* | |
C4 | 0.6885 (4) | −0.2604 (3) | 0.42368 (17) | 0.0559 (11) | |
H4 | 0.7112 | −0.2923 | 0.3941 | 0.067* | |
C5 | 0.7735 (3) | −0.2341 (3) | 0.46587 (15) | 0.0395 (9) | |
C6 | 0.7349 (4) | −0.1900 (4) | 0.50868 (18) | 0.0570 (11) | |
H6 | 0.7896 | −0.1733 | 0.5380 | 0.068* | |
C7 | 0.9010 (3) | −0.2574 (3) | 0.46511 (14) | 0.0385 (9) | |
H7A | 0.9066 | −0.3123 | 0.4372 | 0.046* | |
H7B | 0.9335 | −0.2967 | 0.4972 | 0.046* | |
C8 | 1.2273 (4) | −0.2390 (4) | 0.37217 (17) | 0.0552 (11) | |
H8 | 1.2037 | −0.3051 | 0.3889 | 0.066* | |
C9 | 1.2649 (4) | −0.2526 (5) | 0.3254 (2) | 0.0735 (15) | |
H9 | 1.2662 | −0.3275 | 0.3108 | 0.088* | |
C10 | 1.3005 (4) | −0.1567 (6) | 0.30022 (18) | 0.0767 (15) | |
H10 | 1.3262 | −0.1663 | 0.2686 | 0.092* | |
C11 | 1.2983 (4) | −0.0470 (5) | 0.3216 (2) | 0.0715 (14) | |
H11 | 1.3224 | 0.0186 | 0.3046 | 0.086* | |
C12 | 1.2600 (4) | −0.0331 (4) | 0.36872 (17) | 0.0559 (11) | |
H12 | 1.2588 | 0.0420 | 0.3830 | 0.067* | |
C13 | 1.2238 (3) | −0.1290 (3) | 0.39479 (14) | 0.0368 (8) | |
C14 | 1.1905 (3) | −0.1172 (3) | 0.44700 (15) | 0.0424 (9) | |
H14A | 1.2291 | −0.0467 | 0.4627 | 0.051* | |
H14B | 1.2246 | −0.1840 | 0.4674 | 0.051* | |
C15 | 0.5976 (3) | −0.0233 (3) | 0.30526 (17) | 0.0513 (11) | |
H15 | 0.6308 | −0.0946 | 0.3180 | 0.062* | |
C16 | 0.5459 (4) | −0.0161 (4) | 0.25441 (18) | 0.0633 (13) | |
H16 | 0.5444 | −0.0819 | 0.2330 | 0.076* | |
C17 | 0.4961 (4) | 0.0893 (4) | 0.23504 (18) | 0.0659 (13) | |
H17 | 0.4617 | 0.0952 | 0.2005 | 0.079* | |
C18 | 0.4979 (4) | 0.1853 (4) | 0.26744 (17) | 0.0598 (12) | |
H18 | 0.4635 | 0.2561 | 0.2548 | 0.072* | |
C19 | 0.5501 (3) | 0.1771 (3) | 0.31809 (16) | 0.0498 (10) | |
H19 | 0.5508 | 0.2430 | 0.3394 | 0.060* | |
C20 | 0.6018 (3) | 0.0730 (3) | 0.33828 (15) | 0.0421 (9) | |
C21 | 0.6640 (3) | 0.0670 (3) | 0.39339 (15) | 0.0465 (10) | |
H21A | 0.6591 | −0.0129 | 0.4064 | 0.056* | |
H21B | 0.6255 | 0.1195 | 0.4147 | 0.056* | |
C22 | 1.0230 (4) | 0.1157 (4) | 0.28211 (18) | 0.0604 (12) | |
H22 | 1.0917 | 0.1228 | 0.3060 | 0.072* | |
C23 | 1.0255 (5) | 0.0580 (4) | 0.2367 (2) | 0.0750 (14) | |
H23 | 1.0965 | 0.0274 | 0.2300 | 0.090* | |
C24 | 0.9264 (6) | 0.0440 (4) | 0.20063 (19) | 0.0798 (16) | |
H24 | 0.9290 | 0.0030 | 0.1701 | 0.096* | |
C25 | 0.8232 (5) | 0.0918 (4) | 0.21050 (19) | 0.0741 (15) | |
H25 | 0.7549 | 0.0839 | 0.1864 | 0.089* | |
C26 | 0.8202 (4) | 0.1520 (4) | 0.25627 (17) | 0.0603 (12) | |
H26 | 0.7498 | 0.1850 | 0.2624 | 0.072* | |
C27 | 0.9203 (3) | 0.1637 (3) | 0.29309 (15) | 0.0435 (9) | |
C28 | 0.9156 (4) | 0.2233 (3) | 0.34408 (15) | 0.0543 (11) | |
H28A | 0.8686 | 0.2946 | 0.3377 | 0.065* | |
H28B | 0.9947 | 0.2470 | 0.3592 | 0.065* | |
C29 | 0.9053 (4) | −0.1259 (3) | 0.33632 (14) | 0.0498 (10) | |
H29A | 0.8628 | −0.0833 | 0.3075 | 0.075* | |
H29B | 0.8621 | −0.1956 | 0.3425 | 0.075* | |
H29C | 0.9811 | −0.1482 | 0.3288 | 0.075* | |
C30 | 0.8621 (3) | 0.4827 (3) | 0.53460 (15) | 0.0453 (9) | |
H30 | 0.9356 | 0.4707 | 0.5251 | 0.054* | |
C31 | 0.8547 (4) | 0.5357 (3) | 0.58147 (16) | 0.0509 (10) | |
H31 | 0.9231 | 0.5582 | 0.6033 | 0.061* | |
C32 | 0.7461 (4) | 0.5556 (4) | 0.59623 (18) | 0.0595 (12) | |
C33 | 0.6469 (4) | 0.5159 (4) | 0.56382 (19) | 0.0707 (14) | |
H33 | 0.5736 | 0.5252 | 0.5738 | 0.085* | |
C34 | 0.6540 (4) | 0.4622 (4) | 0.51658 (18) | 0.0634 (12) | |
H34 | 0.5864 | 0.4366 | 0.4951 | 0.076* | |
C35 | 0.7634 (3) | 0.4477 (3) | 0.50208 (15) | 0.0437 (9) | |
C36 | 0.7358 (5) | 0.6198 (4) | 0.6461 (2) | 0.0920 (18) | |
H36A | 0.8128 | 0.6414 | 0.6635 | 0.138* | |
H36B | 0.6990 | 0.5688 | 0.6680 | 0.138* | |
H36C | 0.6890 | 0.6898 | 0.6384 | 0.138* | |
O1 | 0.9200 (2) | −0.05216 (19) | 0.38134 (8) | 0.0369 (6) | |
O2 | 0.94751 (19) | 0.06087 (18) | 0.46365 (8) | 0.0309 (5) | |
O3 | 0.6557 (3) | 0.3742 (3) | 0.41211 (12) | 0.0726 (10) | |
O4 | 0.8481 (3) | 0.4679 (2) | 0.41599 (12) | 0.0740 (9) | |
O5 | 0.8325 (2) | 0.2759 (2) | 0.44978 (10) | 0.0483 (7) | |
Sn1 | 0.84442 (2) | 0.116534 (19) | 0.398869 (9) | 0.03191 (7) | |
Sn2 | 1.009325 (19) | −0.106902 (18) | 0.456013 (9) | 0.02769 (7) | |
S1 | 0.77362 (9) | 0.38944 (8) | 0.43973 (4) | 0.0467 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.056 (3) | 0.089 (4) | 0.100 (4) | −0.004 (3) | 0.031 (3) | −0.015 (3) |
C2 | 0.033 (3) | 0.079 (4) | 0.135 (6) | −0.006 (2) | 0.012 (3) | 0.005 (4) |
C3 | 0.043 (3) | 0.078 (3) | 0.091 (4) | −0.013 (2) | −0.019 (3) | 0.008 (3) |
C4 | 0.054 (3) | 0.056 (3) | 0.053 (3) | −0.010 (2) | −0.004 (2) | 0.000 (2) |
C5 | 0.039 (2) | 0.0277 (17) | 0.050 (2) | −0.0040 (14) | 0.0011 (18) | 0.0042 (16) |
C6 | 0.043 (2) | 0.062 (3) | 0.065 (3) | −0.009 (2) | 0.007 (2) | −0.010 (2) |
C7 | 0.042 (2) | 0.0266 (17) | 0.045 (2) | −0.0005 (14) | 0.0030 (17) | 0.0021 (15) |
C8 | 0.054 (3) | 0.051 (2) | 0.063 (3) | −0.0043 (19) | 0.018 (2) | −0.009 (2) |
C9 | 0.061 (3) | 0.089 (4) | 0.075 (4) | −0.002 (3) | 0.024 (3) | −0.038 (3) |
C10 | 0.060 (3) | 0.136 (5) | 0.038 (3) | −0.012 (3) | 0.020 (2) | −0.011 (3) |
C11 | 0.063 (3) | 0.094 (4) | 0.060 (3) | −0.011 (3) | 0.019 (3) | 0.021 (3) |
C12 | 0.061 (3) | 0.054 (3) | 0.056 (3) | −0.006 (2) | 0.020 (2) | 0.009 (2) |
C13 | 0.0265 (17) | 0.046 (2) | 0.038 (2) | 0.0017 (14) | 0.0069 (15) | −0.0002 (16) |
C14 | 0.0313 (19) | 0.055 (2) | 0.041 (2) | 0.0035 (16) | 0.0082 (16) | 0.0006 (18) |
C15 | 0.044 (2) | 0.046 (2) | 0.061 (3) | 0.0000 (18) | 0.001 (2) | −0.001 (2) |
C16 | 0.059 (3) | 0.066 (3) | 0.062 (3) | −0.004 (2) | 0.002 (2) | −0.022 (2) |
C17 | 0.058 (3) | 0.089 (4) | 0.044 (3) | −0.008 (2) | −0.011 (2) | −0.002 (2) |
C18 | 0.055 (3) | 0.057 (3) | 0.060 (3) | 0.008 (2) | −0.011 (2) | 0.010 (2) |
C19 | 0.048 (2) | 0.044 (2) | 0.053 (3) | 0.0027 (18) | −0.008 (2) | −0.0032 (19) |
C20 | 0.034 (2) | 0.043 (2) | 0.046 (2) | −0.0010 (16) | −0.0008 (17) | −0.0018 (18) |
C21 | 0.042 (2) | 0.047 (2) | 0.048 (2) | −0.0035 (17) | 0.0024 (19) | 0.0099 (19) |
C22 | 0.058 (3) | 0.072 (3) | 0.051 (3) | −0.005 (2) | 0.009 (2) | −0.001 (2) |
C23 | 0.084 (4) | 0.079 (3) | 0.070 (4) | 0.008 (3) | 0.037 (3) | −0.005 (3) |
C24 | 0.129 (5) | 0.074 (3) | 0.044 (3) | −0.019 (3) | 0.038 (3) | −0.008 (2) |
C25 | 0.082 (4) | 0.099 (4) | 0.039 (3) | −0.012 (3) | 0.001 (3) | 0.005 (3) |
C26 | 0.060 (3) | 0.071 (3) | 0.050 (3) | 0.001 (2) | 0.011 (2) | 0.016 (2) |
C27 | 0.053 (2) | 0.041 (2) | 0.039 (2) | −0.0054 (18) | 0.0135 (19) | 0.0079 (17) |
C28 | 0.082 (3) | 0.040 (2) | 0.043 (2) | −0.011 (2) | 0.016 (2) | 0.0018 (18) |
C29 | 0.070 (3) | 0.047 (2) | 0.030 (2) | 0.0069 (19) | −0.0003 (19) | −0.0088 (17) |
C30 | 0.050 (2) | 0.038 (2) | 0.048 (3) | −0.0009 (17) | 0.009 (2) | 0.0003 (18) |
C31 | 0.059 (3) | 0.048 (2) | 0.046 (3) | −0.0091 (19) | 0.009 (2) | −0.0073 (19) |
C32 | 0.069 (3) | 0.054 (3) | 0.056 (3) | 0.000 (2) | 0.014 (3) | −0.006 (2) |
C33 | 0.058 (3) | 0.089 (3) | 0.070 (4) | 0.011 (3) | 0.025 (3) | −0.013 (3) |
C34 | 0.045 (3) | 0.079 (3) | 0.065 (3) | 0.009 (2) | 0.007 (2) | −0.012 (3) |
C35 | 0.051 (2) | 0.037 (2) | 0.045 (2) | 0.0054 (17) | 0.0098 (19) | −0.0037 (17) |
C36 | 0.127 (5) | 0.095 (4) | 0.062 (3) | −0.003 (3) | 0.041 (3) | −0.032 (3) |
O1 | 0.0528 (15) | 0.0330 (12) | 0.0234 (13) | 0.0078 (11) | 0.0017 (11) | −0.0058 (10) |
O2 | 0.0405 (13) | 0.0277 (11) | 0.0226 (12) | 0.0075 (10) | −0.0002 (10) | −0.0002 (9) |
O3 | 0.068 (2) | 0.074 (2) | 0.065 (2) | 0.0164 (16) | −0.0195 (17) | −0.0156 (16) |
O4 | 0.113 (3) | 0.0529 (18) | 0.064 (2) | −0.0100 (17) | 0.038 (2) | 0.0005 (15) |
O5 | 0.0612 (17) | 0.0426 (14) | 0.0393 (15) | 0.0127 (12) | 0.0023 (13) | −0.0162 (12) |
Sn1 | 0.03670 (14) | 0.03096 (13) | 0.02622 (13) | 0.00300 (10) | −0.00032 (10) | 0.00190 (10) |
Sn2 | 0.03021 (12) | 0.02620 (12) | 0.02663 (12) | 0.00233 (9) | 0.00452 (9) | −0.00210 (9) |
S1 | 0.0593 (6) | 0.0383 (5) | 0.0411 (6) | 0.0080 (4) | 0.0038 (5) | −0.0014 (4) |
C1—C2 | 1.363 (7) | C22—H22 | 0.9300 |
C1—C6 | 1.376 (6) | C23—C24 | 1.368 (7) |
C1—H1 | 0.9300 | C23—H23 | 0.9300 |
C2—C3 | 1.354 (7) | C24—C25 | 1.367 (7) |
C2—H2 | 0.9300 | C24—H24 | 0.9300 |
C3—C4 | 1.372 (6) | C25—C26 | 1.385 (6) |
C3—H3 | 0.9300 | C25—H25 | 0.9300 |
C4—C5 | 1.384 (5) | C26—C27 | 1.384 (5) |
C4—H4 | 0.9300 | C26—H26 | 0.9300 |
C5—C6 | 1.367 (6) | C27—C28 | 1.506 (5) |
C5—C7 | 1.495 (5) | C28—H28A | 0.9700 |
C6—H6 | 0.9300 | C28—H28B | 0.9700 |
C7—H7A | 0.9700 | C29—O1 | 1.432 (4) |
C7—H7B | 0.9700 | C29—H29A | 0.9600 |
C8—C9 | 1.375 (6) | C29—H29B | 0.9600 |
C8—C13 | 1.381 (5) | C29—H29C | 0.9600 |
C8—H8 | 0.9300 | C30—C35 | 1.364 (5) |
C9—C10 | 1.366 (7) | C30—C31 | 1.382 (5) |
C9—H9 | 0.9300 | C30—H30 | 0.9300 |
C10—C11 | 1.363 (7) | C31—C32 | 1.387 (6) |
C10—H10 | 0.9300 | C31—H31 | 0.9300 |
C11—C12 | 1.387 (6) | C32—C33 | 1.383 (6) |
C11—H11 | 0.9300 | C32—C36 | 1.517 (6) |
C12—C13 | 1.381 (5) | C33—C34 | 1.394 (6) |
C12—H12 | 0.9300 | C33—H33 | 0.9300 |
C13—C14 | 1.486 (5) | C34—C35 | 1.384 (6) |
C14—H14A | 0.9700 | C34—H34 | 0.9300 |
C14—H14B | 0.9700 | C35—S1 | 1.784 (4) |
C15—C16 | 1.371 (5) | C36—H36A | 0.9600 |
C15—C20 | 1.387 (5) | C36—H36B | 0.9600 |
C15—H15 | 0.9300 | C36—H36C | 0.9600 |
C16—C17 | 1.383 (6) | Sn1—O1 | 2.176 (2) |
C16—H16 | 0.9300 | Sn1—O2 | 2.008 (2) |
C17—C18 | 1.376 (6) | Sn1—O5 | 2.260 (2) |
C17—H17 | 0.9300 | Sn1—C21 | 2.134 (4) |
C18—C19 | 1.368 (5) | Sn1—C28 | 2.140 (4) |
C18—H18 | 0.9300 | Sn2—O2 | 2.047 (2) |
C19—C20 | 1.384 (5) | Sn2—O2i | 2.148 (2) |
C19—H19 | 0.9300 | Sn2—O2i | 2.148 (2) |
C20—C21 | 1.506 (5) | Sn2—C7 | 2.146 (3) |
C21—H21A | 0.9700 | Sn2—C14 | 2.142 (4) |
C21—H21B | 0.9700 | O3—S1 | 1.442 (3) |
C22—C23 | 1.362 (6) | O4—S1 | 1.444 (3) |
C22—C27 | 1.373 (6) | O5—S1 | 1.455 (2) |
C2—C1—C6 | 120.2 (5) | C23—C24—H24 | 120.8 |
C2—C1—H1 | 119.9 | C24—C25—C26 | 120.2 (5) |
C6—C1—H1 | 119.9 | C24—C25—H25 | 119.9 |
C3—C2—C1 | 119.0 (5) | C26—C25—H25 | 119.9 |
C3—C2—H2 | 120.5 | C27—C26—C25 | 121.0 (5) |
C1—C2—H2 | 120.5 | C27—C26—H26 | 119.5 |
C2—C3—C4 | 120.9 (5) | C25—C26—H26 | 119.5 |
C2—C3—H3 | 119.6 | C22—C27—C26 | 117.6 (4) |
C4—C3—H3 | 119.6 | C22—C27—C28 | 121.3 (4) |
C3—C4—C5 | 121.2 (5) | C26—C27—C28 | 121.0 (4) |
C3—C4—H4 | 119.4 | C27—C28—Sn1 | 114.6 (2) |
C5—C4—H4 | 119.4 | C27—C28—H28A | 108.6 |
C6—C5—C4 | 116.9 (4) | Sn1—C28—H28A | 108.6 |
C6—C5—C7 | 121.8 (3) | C27—C28—H28B | 108.6 |
C4—C5—C7 | 121.3 (4) | Sn1—C28—H28B | 108.6 |
C5—C6—C1 | 121.8 (4) | H28A—C28—H28B | 107.6 |
C5—C6—H6 | 119.1 | O1—C29—H29A | 109.5 |
C1—C6—H6 | 119.1 | O1—C29—H29B | 109.5 |
C5—C7—Sn2 | 116.9 (2) | H29A—C29—H29B | 109.5 |
C5—C7—H7A | 108.1 | O1—C29—H29C | 109.5 |
Sn2—C7—H7A | 108.1 | H29A—C29—H29C | 109.5 |
C5—C7—H7B | 108.1 | H29B—C29—H29C | 109.5 |
Sn2—C7—H7B | 108.1 | C35—C30—C31 | 121.0 (4) |
H7A—C7—H7B | 107.3 | C35—C30—H30 | 119.5 |
C9—C8—C13 | 121.3 (4) | C31—C30—H30 | 119.5 |
C9—C8—H8 | 119.3 | C30—C31—C32 | 120.5 (4) |
C13—C8—H8 | 119.3 | C30—C31—H31 | 119.7 |
C10—C9—C8 | 120.3 (4) | C32—C31—H31 | 119.7 |
C10—C9—H9 | 119.8 | C33—C32—C31 | 117.9 (4) |
C8—C9—H9 | 119.8 | C33—C32—C36 | 120.7 (5) |
C11—C10—C9 | 119.7 (4) | C31—C32—C36 | 121.3 (4) |
C11—C10—H10 | 120.1 | C32—C33—C34 | 121.7 (5) |
C9—C10—H10 | 120.1 | C32—C33—H33 | 119.2 |
C10—C11—C12 | 119.9 (4) | C34—C33—H33 | 119.2 |
C10—C11—H11 | 120.0 | C35—C34—C33 | 119.0 (4) |
C12—C11—H11 | 120.0 | C35—C34—H34 | 120.5 |
C13—C12—C11 | 121.2 (4) | C33—C34—H34 | 120.5 |
C13—C12—H12 | 119.4 | C30—C35—C34 | 119.8 (4) |
C11—C12—H12 | 119.4 | C30—C35—S1 | 120.5 (3) |
C8—C13—C12 | 117.4 (4) | C34—C35—S1 | 119.7 (3) |
C8—C13—C14 | 120.4 (3) | C32—C36—H36A | 109.5 |
C12—C13—C14 | 122.0 (3) | C32—C36—H36B | 109.5 |
C13—C14—Sn2 | 120.6 (2) | H36A—C36—H36B | 109.5 |
C13—C14—H14A | 107.2 | C32—C36—H36C | 109.5 |
Sn2—C14—H14A | 107.2 | H36A—C36—H36C | 109.5 |
C13—C14—H14B | 107.2 | H36B—C36—H36C | 109.5 |
Sn2—C14—H14B | 107.2 | C29—O1—Sn2 | 123.9 (2) |
H14A—C14—H14B | 106.8 | C29—O1—Sn1 | 133.3 (2) |
C16—C15—C20 | 121.7 (4) | Sn2—O1—Sn1 | 102.02 (9) |
C16—C15—H15 | 119.1 | Sn1—O2—Sn2 | 112.00 (10) |
C20—C15—H15 | 119.1 | Sn1—O2—Sn2i | 139.81 (11) |
C15—C16—C17 | 119.8 (4) | Sn2—O2—Sn2i | 106.98 (9) |
C15—C16—H16 | 120.1 | S1—O5—Sn1 | 131.89 (15) |
C17—C16—H16 | 120.1 | O2—Sn1—C21 | 114.17 (12) |
C18—C17—C16 | 119.3 (4) | O2—Sn1—C28 | 120.39 (14) |
C18—C17—H17 | 120.4 | C21—Sn1—C28 | 125.36 (16) |
C16—C17—H17 | 120.4 | O2—Sn1—O1 | 72.69 (8) |
C19—C18—C17 | 120.4 (4) | C21—Sn1—O1 | 100.08 (13) |
C19—C18—H18 | 119.8 | C28—Sn1—O1 | 98.14 (13) |
C17—C18—H18 | 119.8 | O2—Sn1—O5 | 80.49 (9) |
C18—C19—C20 | 121.4 (4) | C21—Sn1—O5 | 95.51 (13) |
C18—C19—H19 | 119.3 | C28—Sn1—O5 | 90.81 (13) |
C20—C19—H19 | 119.3 | O1—Sn1—O5 | 152.67 (9) |
C19—C20—C15 | 117.4 (4) | O2—Sn2—C14 | 114.96 (12) |
C19—C20—C21 | 120.9 (3) | O2—Sn2—C7 | 120.35 (12) |
C15—C20—C21 | 121.7 (3) | C14—Sn2—C7 | 124.35 (13) |
C20—C21—Sn1 | 111.0 (3) | O2—Sn2—O2i | 73.02 (9) |
C20—C21—H21A | 109.4 | C14—Sn2—O2i | 92.74 (12) |
Sn1—C21—H21A | 109.4 | C7—Sn2—O2i | 97.39 (11) |
C20—C21—H21B | 109.4 | O2—Sn2—O1 | 72.54 (8) |
Sn1—C21—H21B | 109.4 | C14—Sn2—O1 | 104.19 (12) |
H21A—C21—H21B | 108.0 | C7—Sn2—O1 | 97.42 (11) |
C23—C22—C27 | 121.0 (4) | O2i—Sn2—O1 | 145.45 (8) |
C23—C22—H22 | 119.5 | O3—S1—O4 | 115.8 (2) |
C27—C22—H22 | 119.5 | O3—S1—O5 | 111.00 (16) |
C22—C23—C24 | 121.6 (5) | O4—S1—O5 | 109.10 (19) |
C22—C23—H23 | 119.2 | O3—S1—C35 | 107.8 (2) |
C24—C23—H23 | 119.2 | O4—S1—C35 | 107.54 (18) |
C25—C24—C23 | 118.5 (5) | O5—S1—C35 | 104.95 (16) |
C25—C24—H24 | 120.8 | ||
C6—C1—C2—C3 | −0.3 (8) | Sn2—O2—Sn1—O5 | 178.26 (13) |
C1—C2—C3—C4 | 0.2 (8) | Sn2i—O2—Sn1—O5 | 13.22 (18) |
C2—C3—C4—C5 | −0.8 (7) | C20—C21—Sn1—O2 | −160.3 (2) |
C3—C4—C5—C6 | 1.5 (6) | C20—C21—Sn1—C28 | 22.7 (3) |
C3—C4—C5—C7 | 179.2 (4) | C20—C21—Sn1—O1 | −84.9 (3) |
C4—C5—C6—C1 | −1.7 (6) | C20—C21—Sn1—O5 | 117.6 (3) |
C7—C5—C6—C1 | −179.3 (4) | C27—C28—Sn1—O2 | 112.3 (3) |
C2—C1—C6—C5 | 1.1 (7) | C27—C28—Sn1—C21 | −70.9 (4) |
C6—C5—C7—Sn2 | −77.6 (4) | C27—C28—Sn1—O1 | 37.7 (3) |
C4—C5—C7—Sn2 | 104.8 (3) | C27—C28—Sn1—O5 | −168.2 (3) |
C13—C8—C9—C10 | 0.3 (7) | C29—O1—Sn1—O2 | 176.6 (3) |
C8—C9—C10—C11 | −0.2 (8) | Sn2—O1—Sn1—O2 | 6.36 (9) |
C9—C10—C11—C12 | 0.1 (7) | C29—O1—Sn1—C21 | 64.2 (3) |
C10—C11—C12—C13 | 0.0 (7) | Sn2—O1—Sn1—C21 | −105.98 (13) |
C9—C8—C13—C12 | −0.3 (6) | C29—O1—Sn1—C28 | −64.0 (3) |
C9—C8—C13—C14 | −175.8 (4) | Sn2—O1—Sn1—C28 | 125.75 (14) |
C11—C12—C13—C8 | 0.1 (6) | C29—O1—Sn1—O5 | −171.9 (3) |
C11—C12—C13—C14 | 175.6 (4) | Sn2—O1—Sn1—O5 | 17.8 (3) |
C8—C13—C14—Sn2 | −85.0 (4) | S1—O5—Sn1—O2 | 177.3 (2) |
C12—C13—C14—Sn2 | 99.6 (4) | S1—O5—Sn1—C21 | −69.1 (2) |
C20—C15—C16—C17 | −0.1 (7) | S1—O5—Sn1—C28 | 56.6 (3) |
C15—C16—C17—C18 | −0.8 (7) | S1—O5—Sn1—O1 | 166.20 (17) |
C16—C17—C18—C19 | 1.0 (7) | Sn1—O2—Sn2—C14 | 105.02 (14) |
C17—C18—C19—C20 | −0.3 (7) | Sn2i—O2—Sn2—C14 | −85.01 (15) |
C18—C19—C20—C15 | −0.6 (6) | Sn1—O2—Sn2—C7 | −81.28 (16) |
C18—C19—C20—C21 | 177.0 (4) | Sn2i—O2—Sn2—C7 | 88.68 (14) |
C16—C15—C20—C19 | 0.8 (6) | Sn1—O2—Sn2—O2i | −169.97 (18) |
C16—C15—C20—C21 | −176.8 (4) | Sn2i—O2—Sn2—O2i | 0.0 |
C19—C20—C21—Sn1 | −88.0 (4) | Sn1—O2—Sn2—O1 | 7.15 (10) |
C15—C20—C21—Sn1 | 89.5 (4) | Sn2i—O2—Sn2—O1 | 177.12 (13) |
C27—C22—C23—C24 | −0.9 (7) | C13—C14—Sn2—O2 | −97.7 (3) |
C22—C23—C24—C25 | 1.4 (8) | C13—C14—Sn2—C7 | 88.9 (3) |
C23—C24—C25—C26 | −0.5 (8) | C13—C14—Sn2—O2i | −170.2 (3) |
C24—C25—C26—C27 | −0.9 (7) | C13—C14—Sn2—O1 | −20.6 (3) |
C23—C22—C27—C26 | −0.4 (6) | C5—C7—Sn2—O2 | 12.6 (3) |
C23—C22—C27—C28 | 177.5 (4) | C5—C7—Sn2—C14 | −174.4 (3) |
C25—C26—C27—C22 | 1.3 (6) | C5—C7—Sn2—O2i | 87.2 (3) |
C25—C26—C27—C28 | −176.6 (4) | C5—C7—Sn2—O1 | −61.5 (3) |
C22—C27—C28—Sn1 | −100.3 (4) | C29—O1—Sn2—O2 | −177.7 (3) |
C26—C27—C28—Sn1 | 77.5 (4) | Sn1—O1—Sn2—O2 | −6.25 (9) |
C35—C30—C31—C32 | −0.7 (6) | C29—O1—Sn2—C14 | 70.2 (3) |
C30—C31—C32—C33 | 3.0 (6) | Sn1—O1—Sn2—C14 | −118.38 (13) |
C30—C31—C32—C36 | −176.5 (4) | C29—O1—Sn2—C7 | −58.1 (3) |
C31—C32—C33—C34 | −2.9 (7) | Sn1—O1—Sn2—C7 | 113.31 (13) |
C36—C32—C33—C34 | 176.6 (5) | C29—O1—Sn2—O2i | −172.8 (2) |
C32—C33—C34—C35 | 0.5 (7) | Sn1—O1—Sn2—O2i | −1.4 (2) |
C31—C30—C35—C34 | −1.8 (6) | Sn1—O5—S1—O3 | 45.4 (3) |
C31—C30—C35—S1 | 175.4 (3) | Sn1—O5—S1—O4 | −83.3 (2) |
C33—C34—C35—C30 | 1.9 (6) | Sn1—O5—S1—C35 | 161.7 (2) |
C33—C34—C35—S1 | −175.3 (3) | C30—C35—S1—O3 | −173.1 (3) |
Sn2—O2—Sn1—C21 | 86.45 (16) | C34—C35—S1—O3 | 4.1 (4) |
Sn2i—O2—Sn1—C21 | −78.6 (2) | C30—C35—S1—O4 | −47.5 (4) |
Sn2—O2—Sn1—C28 | −96.43 (16) | C34—C35—S1—O4 | 129.6 (4) |
Sn2i—O2—Sn1—C28 | 98.5 (2) | C30—C35—S1—O5 | 68.5 (3) |
Sn2—O2—Sn1—O1 | −7.05 (10) | C34—C35—S1—O5 | −114.3 (3) |
Sn2i—O2—Sn1—O1 | −172.1 (2) |
Symmetry code: (i) −x+2, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Sn4(C7H7)8(CH3O)2(C7H7O3S)2O2] |
Mr | 1640.21 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.520 (5), 11.302 (4), 26.219 (11) |
β (°) | 99.409 (1) |
V (Å3) | 3368 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.59 |
Crystal size (mm) | 0.43 × 0.15 × 0.13 |
Data collection | |
Diffractometer | Bruker APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.747, 0.820 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20431, 7979, 5980 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.077, 1.04 |
No. of reflections | 7979 |
No. of parameters | 397 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.74, −0.88 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SAINT (Bruker, 1999, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
Sn1—O1 | 2.176 (2) | Sn2—O2 | 2.047 (2) |
Sn1—O2 | 2.008 (2) | Sn2—O2i | 2.148 (2) |
Sn1—O5 | 2.260 (2) | Sn2—C7 | 2.146 (3) |
Sn1—C21 | 2.134 (4) | Sn2—C14 | 2.142 (4) |
Sn1—C28 | 2.140 (4) |
Symmetry code: (i) −x+2, −y, −z+1. |
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Some organotin(IV) derivatives of sulfonates show antitumor activities (Chandrasekhar et al., 2003). In this paper, we report the structure of a new organotin sulfonate, [Sn4(Bz)8(L)2(OCH3)2(O)2], (I), where Bz = the benzyl group and L = p-toluenesulfonate.
Selected bond lengths for (I) are listed in Table 1. Both Sn(IV) atoms are five-coordinated in distorted trigonal–bipyramidal geometries. The exo tin atom (Sn1) is coordinated by two benzyl groups, one µ3-O2- anion, one µ2-OCH3- anion and one L O atom. The endo tin atom (Sn2) is coordinated by two benzyl groups, two µ3-O2- anions, one µ2-OCH3- anion and one L O atom. The four Sn(IV) atoms are connected by two µ3-O2- anions, generating the title Sn—O ladder structure. The p-toluenesulfonate anions and µ2-OCH3- anion are attached on both sides of the ladder.