Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046338/tk2196sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046338/tk2196Isup2.hkl |
CCDC reference: 663647
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.013 Å
- R factor = 0.064
- wR factor = 0.142
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 13
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Anderson et al. (1997); Li et al. (2007); Garnovski et al. (1993); Nath et al. (1997).
The Schiff-base ligand was synthesized by the reaction of salicylaldehyde and 4-aminothiophenol in ethanol solution. Under an N2 atmosphere, the Schiff-base (0.229 g, 1 mmol) and (C6H5)3SnCl (0.385 g, 1 mmol) were added to a solution of dry benzene (30 ml) in a Schlenk flask and stirred under reflux conditions (353 K) for 12 h. The solution was filtered and after a week yellow crystals suitable for X-ray diffraction study were obtained. Yield, 0.503 g, 82%. m.p. 430–432 K.
Analysis found: C 64.32, H 4.45, N 2.38, O 2.75, S 5.50%; C19H19NOSSn requires: C 64.38, H 4.36, N 2.42, O 2.77, S 5.54%.
The H-atoms were included in the riding-model approximation with C—H = 0.93 Å and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C-aromatic) and Uiso(H) = 1.5Ueq(O). The maximum and minimum residual electron denisty peaks were located 1.68 and 1.20 Å, respectively, from the O2 and Sn2 atoms.
Recently, a number of Schiff-bases have been investigated in terms of their crystallography and coordination chemistry (Garnovski et al., 1993). During the last decade, Schiff-base complexes have been applied in catalytic reactions and biological systems (Anderson et al., 1997). Organotin complexes containing Schiff-bases have attracted much attention owing to their potential biological activities (Nath et al., 1997). The title compound (I) was synthesized and its crystal structure determined (Fig. 1 and Table 1). Two independent molecules comprise the crystallographic asymmetric unit. In each of these, the central tin atom exists in a distorted tetrahedron defined by a C3S donor set. The geometric parameters are in good agreement with those found in (4,5-diphenyl-4-oxazoline-2-thiolato)triphenyltin (Li et al., 2007). The mean planes of the two benzene rings in (I) make a dihedral angle of 31.0 (5)° (molecule 1) and 31.3 (6)° (molecule 2) showing that the Schiff-base ligand adopts a non-planar conformation in each case.
For related literature, see: Anderson et al. (1997); Li et al. (2007); Garnovski et al. (1993); Nath et al. (1997).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
[Sn(C6H5)3(C13H10NOS)] | Z = 4 |
Mr = 578.27 | F(000) = 1168 |
Triclinic, P1 | Dx = 1.447 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5561 (10) Å | Cell parameters from 4515 reflections |
b = 9.6073 (11) Å | θ = 2.3–24.1° |
c = 30.110 (3) Å | µ = 1.07 mm−1 |
α = 92.064 (2)° | T = 298 K |
β = 95.430 (2)° | Block, yellow |
γ = 104.936 (3)° | 0.15 × 0.12 × 0.10 mm |
V = 2653.8 (5) Å3 |
Bruker SMART CCD area-detector diffractometer | 9194 independent reflections |
Radiation source: sealed tube | 6702 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.857, Tmax = 0.901 | k = −11→11 |
13756 measured reflections | l = −35→24 |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + 13.8664P] where P = (Fo2 + 2Fc2)/3 |
9194 reflections | (Δ/σ)max = 0.001 |
631 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −1.26 e Å−3 |
[Sn(C6H5)3(C13H10NOS)] | γ = 104.936 (3)° |
Mr = 578.27 | V = 2653.8 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.5561 (10) Å | Mo Kα radiation |
b = 9.6073 (11) Å | µ = 1.07 mm−1 |
c = 30.110 (3) Å | T = 298 K |
α = 92.064 (2)° | 0.15 × 0.12 × 0.10 mm |
β = 95.430 (2)° |
Bruker SMART CCD area-detector diffractometer | 9194 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 6702 reflections with I > 2σ(I) |
Tmin = 0.857, Tmax = 0.901 | Rint = 0.046 |
13756 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + 13.8664P] where P = (Fo2 + 2Fc2)/3 |
9194 reflections | Δρmax = 0.58 e Å−3 |
631 parameters | Δρmin = −1.26 e Å−3 |
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 | ||
Sn1 | 0.83590 (5) | 0.29973 (5) | 0.379460 (17) | 0.04023 (15) | |
Sn2 | 0.18962 (6) | 0.14815 (6) | 0.123781 (17) | 0.04579 (17) | |
N1 | 0.8033 (7) | 0.2038 (6) | 0.6046 (2) | 0.0445 (15) | |
N2 | 0.3049 (7) | 0.2040 (7) | −0.0979 (2) | 0.0497 (16) | |
O1 | 0.9884 (6) | 0.3102 (7) | 0.6745 (2) | 0.0760 (18) | |
H1 | 0.9593 | 0.2891 | 0.6480 | 0.114* | |
O2 | 0.2069 (8) | 0.0204 (6) | −0.1663 (2) | 0.082 (2) | |
H2 | 0.2270 | 0.0490 | −0.1399 | 0.123* | |
S1 | 0.6851 (2) | 0.0845 (2) | 0.40714 (7) | 0.0572 (6) | |
S2 | 0.4112 (2) | 0.3014 (3) | 0.10086 (7) | 0.0626 (6) | |
C1 | 0.7213 (8) | 0.1246 (7) | 0.4656 (2) | 0.0429 (18) | |
C2 | 0.8510 (9) | 0.1208 (8) | 0.4893 (3) | 0.053 (2) | |
H2A | 0.9235 | 0.0990 | 0.4740 | 0.063* | |
C3 | 0.8760 (8) | 0.1484 (8) | 0.5349 (3) | 0.051 (2) | |
H3 | 0.9654 | 0.1475 | 0.5498 | 0.061* | |
C4 | 0.7693 (8) | 0.1772 (7) | 0.5583 (3) | 0.0419 (17) | |
C5 | 0.6407 (8) | 0.1816 (8) | 0.5353 (3) | 0.051 (2) | |
H5 | 0.5679 | 0.2018 | 0.5508 | 0.062* | |
C6 | 0.6166 (8) | 0.1569 (8) | 0.4900 (3) | 0.051 (2) | |
H6 | 0.5283 | 0.1618 | 0.4752 | 0.061* | |
C7 | 0.7035 (9) | 0.1796 (8) | 0.6311 (3) | 0.051 (2) | |
H7 | 0.6075 | 0.1399 | 0.6191 | 0.061* | |
C8 | 0.7341 (9) | 0.2112 (8) | 0.6789 (3) | 0.0480 (19) | |
C9 | 0.8756 (9) | 0.2730 (8) | 0.6991 (3) | 0.052 (2) | |
C10 | 0.9019 (11) | 0.2999 (10) | 0.7448 (3) | 0.068 (2) | |
H10 | 0.9959 | 0.3420 | 0.7582 | 0.081* | |
C11 | 0.7879 (11) | 0.2639 (10) | 0.7704 (3) | 0.066 (2) | |
H11 | 0.8063 | 0.2830 | 0.8012 | 0.080* | |
C12 | 0.6478 (12) | 0.2006 (10) | 0.7521 (3) | 0.070 (3) | |
H12 | 0.5721 | 0.1762 | 0.7701 | 0.085* | |
C13 | 0.6225 (10) | 0.1743 (9) | 0.7064 (3) | 0.062 (2) | |
H13 | 0.5282 | 0.1308 | 0.6935 | 0.075* | |
C14 | 0.7899 (7) | 0.4815 (7) | 0.4112 (2) | 0.0368 (16) | |
C15 | 0.8120 (9) | 0.5105 (8) | 0.4571 (2) | 0.055 (2) | |
H15 | 0.8518 | 0.4512 | 0.4753 | 0.066* | |
C16 | 0.7750 (10) | 0.6266 (9) | 0.4756 (3) | 0.071 (3) | |
H16 | 0.7861 | 0.6433 | 0.5065 | 0.085* | |
C17 | 0.7216 (10) | 0.7190 (9) | 0.4491 (4) | 0.070 (3) | |
H17 | 0.6991 | 0.7992 | 0.4618 | 0.084* | |
C18 | 0.7028 (10) | 0.6922 (9) | 0.4055 (3) | 0.070 (3) | |
H18 | 0.6670 | 0.7549 | 0.3876 | 0.084* | |
C19 | 0.7343 (9) | 0.5744 (7) | 0.3855 (3) | 0.053 (2) | |
H19 | 0.7181 | 0.5576 | 0.3546 | 0.063* | |
C20 | 0.7698 (7) | 0.2763 (7) | 0.3100 (2) | 0.0404 (17) | |
C21 | 0.6255 (8) | 0.2188 (9) | 0.2936 (3) | 0.057 (2) | |
H21 | 0.5558 | 0.1919 | 0.3134 | 0.068* | |
C22 | 0.5833 (10) | 0.2009 (10) | 0.2481 (3) | 0.069 (3) | |
H22 | 0.4864 | 0.1602 | 0.2373 | 0.083* | |
C23 | 0.6877 (11) | 0.2443 (10) | 0.2189 (3) | 0.070 (3) | |
H23 | 0.6606 | 0.2330 | 0.1882 | 0.084* | |
C24 | 0.8268 (12) | 0.3024 (11) | 0.2345 (3) | 0.075 (3) | |
H24 | 0.8961 | 0.3317 | 0.2146 | 0.090* | |
C25 | 0.8690 (9) | 0.3195 (9) | 0.2807 (3) | 0.056 (2) | |
H25 | 0.9660 | 0.3610 | 0.2913 | 0.067* | |
C26 | 1.0586 (7) | 0.3039 (7) | 0.3935 (2) | 0.0353 (15) | |
C27 | 1.1091 (9) | 0.1821 (8) | 0.3947 (3) | 0.0479 (19) | |
H27 | 1.0430 | 0.0916 | 0.3905 | 0.058* | |
C28 | 1.2557 (9) | 0.1921 (9) | 0.4023 (3) | 0.060 (2) | |
H28 | 1.2873 | 0.1083 | 0.4030 | 0.072* | |
C29 | 1.3557 (9) | 0.3235 (10) | 0.4086 (3) | 0.058 (2) | |
H29 | 1.4545 | 0.3298 | 0.4146 | 0.070* | |
C30 | 1.3080 (9) | 0.4440 (9) | 0.4061 (3) | 0.064 (2) | |
H30 | 1.3748 | 0.5341 | 0.4087 | 0.077* | |
C31 | 1.1602 (9) | 0.4342 (8) | 0.3998 (3) | 0.054 (2) | |
H31 | 1.1293 | 0.5185 | 0.3999 | 0.065* | |
C32 | 0.3776 (8) | 0.2722 (8) | 0.0419 (3) | 0.0488 (19) | |
C33 | 0.3434 (10) | 0.3769 (10) | 0.0168 (3) | 0.064 (2) | |
H33 | 0.3351 | 0.4618 | 0.0309 | 0.077* | |
C34 | 0.3212 (10) | 0.3583 (9) | −0.0289 (3) | 0.065 (2) | |
H34 | 0.3004 | 0.4320 | −0.0454 | 0.078* | |
C35 | 0.3290 (8) | 0.2332 (8) | −0.0509 (3) | 0.0444 (18) | |
C36 | 0.3589 (9) | 0.1266 (8) | −0.0257 (3) | 0.055 (2) | |
H36 | 0.3618 | 0.0397 | −0.0397 | 0.066* | |
C37 | 0.3850 (9) | 0.1462 (9) | 0.0206 (3) | 0.057 (2) | |
H37 | 0.4076 | 0.0736 | 0.0372 | 0.068* | |
C38 | 0.3319 (7) | 0.3032 (8) | −0.1252 (3) | 0.049 (2) | |
H38 | 0.3701 | 0.3981 | −0.1137 | 0.058* | |
C39 | 0.3061 (8) | 0.2756 (9) | −0.1726 (3) | 0.053 (2) | |
C40 | 0.2437 (9) | 0.1339 (9) | −0.1923 (3) | 0.058 (2) | |
C41 | 0.2205 (11) | 0.1116 (10) | −0.2381 (3) | 0.071 (3) | |
H41 | 0.1795 | 0.0190 | −0.2512 | 0.085* | |
C42 | 0.2583 (10) | 0.2268 (12) | −0.2648 (3) | 0.073 (3) | |
H42 | 0.2435 | 0.2116 | −0.2957 | 0.087* | |
C43 | 0.3175 (11) | 0.3630 (12) | −0.2456 (4) | 0.079 (3) | |
H43 | 0.3429 | 0.4402 | −0.2636 | 0.095* | |
C44 | 0.3394 (10) | 0.3865 (9) | −0.2005 (3) | 0.067 (2) | |
H44 | 0.3781 | 0.4803 | −0.1882 | 0.080* | |
C45 | 0.0125 (8) | 0.1969 (7) | 0.0849 (3) | 0.0459 (18) | |
C46 | −0.0866 (10) | 0.2497 (9) | 0.1066 (3) | 0.070 (3) | |
H46 | −0.0772 | 0.2590 | 0.1377 | 0.084* | |
C47 | −0.1986 (10) | 0.2886 (9) | 0.0826 (3) | 0.071 (3) | |
H47 | −0.2627 | 0.3270 | 0.0974 | 0.085* | |
C48 | −0.2159 (10) | 0.2708 (10) | 0.0366 (3) | 0.072 (3) | |
H48 | −0.2930 | 0.2950 | 0.0204 | 0.086* | |
C49 | −0.1210 (9) | 0.2182 (11) | 0.0153 (3) | 0.074 (3) | |
H49 | −0.1319 | 0.2067 | −0.0157 | 0.089* | |
C50 | −0.0074 (9) | 0.1813 (10) | 0.0397 (3) | 0.060 (2) | |
H50 | 0.0572 | 0.1447 | 0.0246 | 0.072* | |
C51 | 0.2063 (8) | 0.2095 (8) | 0.1928 (2) | 0.0425 (17) | |
C52 | 0.2661 (9) | 0.3513 (9) | 0.2087 (3) | 0.053 (2) | |
H52 | 0.2955 | 0.4224 | 0.1888 | 0.064* | |
C53 | 0.2822 (10) | 0.3874 (10) | 0.2542 (3) | 0.070 (3) | |
H53 | 0.3217 | 0.4831 | 0.2646 | 0.084* | |
C54 | 0.2416 (11) | 0.2861 (12) | 0.2837 (3) | 0.071 (3) | |
H54 | 0.2522 | 0.3116 | 0.3141 | 0.086* | |
C55 | 0.1846 (11) | 0.1458 (11) | 0.2682 (3) | 0.074 (3) | |
H55 | 0.1579 | 0.0755 | 0.2885 | 0.088* | |
C56 | 0.1659 (9) | 0.1061 (9) | 0.2231 (3) | 0.058 (2) | |
H56 | 0.1263 | 0.0099 | 0.2131 | 0.070* | |
C57 | 0.1900 (7) | −0.0722 (7) | 0.1137 (2) | 0.0440 (17) | |
C58 | 0.0583 (8) | −0.1736 (8) | 0.1075 (3) | 0.062 (2) | |
H58 | −0.0271 | −0.1440 | 0.1074 | 0.074* | |
C59 | 0.0497 (10) | −0.3186 (10) | 0.1016 (3) | 0.077 (3) | |
H59 | −0.0410 | −0.3853 | 0.0968 | 0.093* | |
C60 | 0.1745 (10) | −0.3652 (10) | 0.1027 (3) | 0.069 (3) | |
H60 | 0.1690 | −0.4632 | 0.0997 | 0.083* | |
C61 | 0.3038 (11) | −0.2672 (10) | 0.1081 (4) | 0.082 (3) | |
H61 | 0.3886 | −0.2975 | 0.1077 | 0.098* | |
C62 | 0.3137 (8) | −0.1205 (9) | 0.1143 (3) | 0.069 (2) | |
H62 | 0.4047 | −0.0546 | 0.1190 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0453 (3) | 0.0343 (3) | 0.0401 (3) | 0.0108 (2) | −0.0004 (2) | −0.0004 (2) |
Sn2 | 0.0435 (3) | 0.0486 (3) | 0.0428 (3) | 0.0098 (3) | 0.0006 (2) | −0.0022 (2) |
N1 | 0.051 (4) | 0.034 (3) | 0.049 (4) | 0.012 (3) | 0.003 (3) | 0.010 (3) |
N2 | 0.044 (4) | 0.046 (4) | 0.060 (4) | 0.011 (3) | 0.010 (3) | 0.005 (3) |
O1 | 0.049 (4) | 0.112 (5) | 0.056 (4) | 0.005 (3) | 0.000 (3) | 0.004 (4) |
O2 | 0.136 (6) | 0.050 (4) | 0.058 (4) | 0.015 (4) | 0.024 (4) | 0.008 (3) |
S1 | 0.0698 (14) | 0.0401 (11) | 0.0488 (12) | −0.0052 (10) | −0.0032 (10) | 0.0021 (9) |
S2 | 0.0473 (12) | 0.0721 (15) | 0.0532 (13) | −0.0083 (11) | −0.0003 (10) | −0.0045 (11) |
C1 | 0.052 (5) | 0.026 (3) | 0.044 (4) | −0.001 (3) | 0.000 (4) | 0.004 (3) |
C2 | 0.053 (5) | 0.057 (5) | 0.052 (5) | 0.020 (4) | 0.009 (4) | 0.011 (4) |
C3 | 0.041 (4) | 0.055 (5) | 0.054 (5) | 0.009 (4) | −0.002 (4) | 0.009 (4) |
C4 | 0.046 (4) | 0.026 (4) | 0.051 (5) | 0.004 (3) | 0.004 (4) | 0.002 (3) |
C5 | 0.041 (5) | 0.059 (5) | 0.050 (5) | 0.008 (4) | 0.002 (4) | −0.003 (4) |
C6 | 0.041 (5) | 0.050 (5) | 0.060 (5) | 0.011 (4) | −0.002 (4) | 0.009 (4) |
C7 | 0.054 (5) | 0.033 (4) | 0.061 (5) | 0.005 (4) | 0.000 (4) | −0.002 (4) |
C8 | 0.053 (5) | 0.039 (4) | 0.054 (5) | 0.015 (4) | 0.005 (4) | 0.002 (4) |
C9 | 0.053 (5) | 0.049 (5) | 0.051 (5) | 0.012 (4) | 0.003 (4) | 0.004 (4) |
C10 | 0.068 (6) | 0.085 (7) | 0.053 (6) | 0.028 (5) | −0.003 (5) | 0.005 (5) |
C11 | 0.088 (7) | 0.065 (6) | 0.050 (5) | 0.027 (5) | 0.004 (5) | 0.002 (4) |
C12 | 0.083 (7) | 0.069 (6) | 0.064 (6) | 0.021 (5) | 0.027 (5) | 0.013 (5) |
C13 | 0.055 (5) | 0.065 (6) | 0.067 (6) | 0.013 (4) | 0.014 (5) | 0.014 (5) |
C14 | 0.031 (4) | 0.032 (4) | 0.049 (4) | 0.009 (3) | 0.006 (3) | 0.006 (3) |
C15 | 0.080 (6) | 0.037 (4) | 0.046 (5) | 0.015 (4) | 0.002 (4) | −0.001 (4) |
C16 | 0.084 (7) | 0.062 (6) | 0.059 (6) | 0.008 (5) | 0.015 (5) | −0.020 (5) |
C17 | 0.064 (6) | 0.047 (5) | 0.102 (8) | 0.019 (5) | 0.019 (6) | −0.025 (5) |
C18 | 0.073 (6) | 0.053 (5) | 0.089 (8) | 0.029 (5) | 0.004 (5) | 0.003 (5) |
C19 | 0.059 (5) | 0.041 (4) | 0.059 (5) | 0.015 (4) | 0.002 (4) | 0.005 (4) |
C20 | 0.050 (5) | 0.033 (4) | 0.042 (4) | 0.018 (3) | 0.006 (4) | 0.004 (3) |
C21 | 0.049 (5) | 0.067 (5) | 0.053 (5) | 0.012 (4) | 0.002 (4) | 0.000 (4) |
C22 | 0.063 (6) | 0.076 (6) | 0.062 (6) | 0.016 (5) | −0.019 (5) | −0.007 (5) |
C23 | 0.099 (8) | 0.076 (6) | 0.038 (5) | 0.035 (6) | −0.009 (5) | −0.003 (5) |
C24 | 0.088 (8) | 0.087 (7) | 0.053 (6) | 0.023 (6) | 0.019 (5) | −0.003 (5) |
C25 | 0.048 (5) | 0.059 (5) | 0.055 (5) | 0.006 (4) | 0.004 (4) | −0.005 (4) |
C26 | 0.043 (4) | 0.029 (3) | 0.035 (4) | 0.013 (3) | 0.000 (3) | −0.002 (3) |
C27 | 0.056 (5) | 0.033 (4) | 0.055 (5) | 0.011 (4) | 0.008 (4) | 0.008 (3) |
C28 | 0.060 (6) | 0.051 (5) | 0.080 (6) | 0.035 (5) | 0.009 (5) | 0.021 (5) |
C29 | 0.050 (5) | 0.077 (6) | 0.054 (5) | 0.028 (5) | 0.002 (4) | 0.012 (5) |
C30 | 0.054 (5) | 0.046 (5) | 0.081 (7) | −0.004 (4) | −0.002 (5) | −0.002 (4) |
C31 | 0.052 (5) | 0.030 (4) | 0.080 (6) | 0.017 (4) | −0.005 (4) | −0.003 (4) |
C32 | 0.038 (4) | 0.053 (5) | 0.053 (5) | 0.006 (4) | 0.012 (4) | 0.004 (4) |
C33 | 0.081 (7) | 0.058 (5) | 0.051 (5) | 0.014 (5) | 0.006 (5) | −0.004 (4) |
C34 | 0.087 (7) | 0.048 (5) | 0.066 (6) | 0.026 (5) | 0.007 (5) | 0.005 (4) |
C35 | 0.034 (4) | 0.047 (4) | 0.049 (5) | 0.005 (3) | 0.004 (3) | −0.001 (4) |
C36 | 0.065 (6) | 0.044 (4) | 0.061 (6) | 0.021 (4) | 0.018 (4) | 0.007 (4) |
C37 | 0.062 (5) | 0.062 (5) | 0.057 (5) | 0.029 (4) | 0.018 (4) | 0.018 (4) |
C38 | 0.032 (4) | 0.039 (4) | 0.070 (6) | 0.002 (3) | 0.003 (4) | −0.002 (4) |
C39 | 0.041 (5) | 0.051 (5) | 0.068 (6) | 0.011 (4) | 0.004 (4) | 0.008 (4) |
C40 | 0.060 (5) | 0.061 (5) | 0.054 (5) | 0.017 (4) | 0.008 (4) | 0.010 (4) |
C41 | 0.088 (7) | 0.064 (6) | 0.057 (6) | 0.016 (5) | 0.008 (5) | −0.004 (5) |
C42 | 0.072 (7) | 0.111 (9) | 0.048 (5) | 0.043 (6) | 0.008 (5) | 0.009 (6) |
C43 | 0.073 (7) | 0.082 (7) | 0.075 (7) | 0.008 (6) | −0.004 (6) | 0.026 (6) |
C44 | 0.073 (6) | 0.051 (5) | 0.070 (7) | 0.007 (5) | 0.000 (5) | 0.010 (5) |
C45 | 0.045 (4) | 0.040 (4) | 0.054 (5) | 0.009 (3) | 0.010 (4) | 0.008 (4) |
C46 | 0.071 (6) | 0.063 (6) | 0.079 (7) | 0.022 (5) | 0.020 (5) | 0.003 (5) |
C47 | 0.055 (6) | 0.054 (5) | 0.107 (9) | 0.018 (5) | 0.022 (6) | 0.005 (5) |
C48 | 0.055 (6) | 0.064 (6) | 0.100 (8) | 0.026 (5) | −0.013 (6) | 0.012 (6) |
C49 | 0.063 (6) | 0.090 (7) | 0.059 (6) | 0.010 (5) | −0.012 (5) | 0.000 (5) |
C50 | 0.053 (5) | 0.082 (6) | 0.046 (5) | 0.025 (5) | −0.001 (4) | −0.012 (4) |
C51 | 0.041 (4) | 0.044 (4) | 0.044 (4) | 0.014 (3) | 0.002 (3) | 0.003 (3) |
C52 | 0.065 (5) | 0.054 (5) | 0.041 (5) | 0.019 (4) | 0.003 (4) | 0.001 (4) |
C53 | 0.081 (7) | 0.065 (6) | 0.065 (6) | 0.023 (5) | 0.004 (5) | −0.021 (5) |
C54 | 0.076 (7) | 0.097 (8) | 0.050 (6) | 0.035 (6) | 0.018 (5) | 0.002 (6) |
C55 | 0.097 (8) | 0.084 (7) | 0.052 (6) | 0.037 (6) | 0.025 (5) | 0.023 (5) |
C56 | 0.071 (6) | 0.055 (5) | 0.051 (5) | 0.020 (4) | 0.009 (4) | 0.010 (4) |
C57 | 0.037 (4) | 0.052 (4) | 0.043 (4) | 0.010 (3) | 0.007 (3) | 0.001 (3) |
C58 | 0.043 (4) | 0.049 (5) | 0.095 (6) | 0.017 (4) | 0.003 (4) | −0.005 (4) |
C59 | 0.067 (6) | 0.064 (6) | 0.092 (8) | 0.009 (5) | −0.003 (5) | −0.011 (5) |
C60 | 0.082 (7) | 0.054 (5) | 0.076 (7) | 0.022 (5) | 0.017 (5) | 0.006 (5) |
C61 | 0.075 (7) | 0.081 (7) | 0.119 (9) | 0.059 (6) | 0.036 (6) | 0.033 (6) |
C62 | 0.044 (5) | 0.078 (6) | 0.085 (6) | 0.017 (4) | 0.007 (4) | 0.016 (5) |
Sn1—S1 | 2.421 (2) | C27—C28 | 1.376 (11) |
Sn1—C14 | 2.124 (6) | C27—H27 | 0.9300 |
Sn1—C20 | 2.113 (7) | C28—C29 | 1.367 (12) |
Sn1—C26 | 2.120 (7) | C28—H28 | 0.9300 |
Sn2—S2 | 2.423 (2) | C29—C30 | 1.351 (11) |
Sn2—C45 | 2.127 (7) | C29—H29 | 0.9300 |
Sn2—C51 | 2.120 (7) | C30—C31 | 1.385 (11) |
Sn2—C57 | 2.129 (7) | C30—H30 | 0.9300 |
N1—C7 | 1.281 (9) | C31—H31 | 0.9300 |
N1—C4 | 1.401 (9) | C32—C33 | 1.366 (11) |
N2—C38 | 1.273 (9) | C32—C37 | 1.370 (11) |
N2—C35 | 1.417 (10) | C33—C34 | 1.370 (12) |
O1—C9 | 1.345 (9) | C33—H33 | 0.9300 |
O1—H1 | 0.8200 | C34—C35 | 1.375 (11) |
O2—C40 | 1.358 (9) | C34—H34 | 0.9300 |
O2—H2 | 0.8200 | C35—C36 | 1.369 (10) |
S1—C1 | 1.771 (7) | C36—C37 | 1.391 (11) |
S2—C32 | 1.774 (8) | C36—H36 | 0.9300 |
C1—C2 | 1.379 (10) | C37—H37 | 0.9300 |
C1—C6 | 1.385 (10) | C38—C39 | 1.429 (11) |
C2—C3 | 1.374 (11) | C38—H38 | 0.9300 |
C2—H2A | 0.9300 | C39—C44 | 1.372 (11) |
C3—C4 | 1.372 (10) | C39—C40 | 1.420 (11) |
C3—H3 | 0.9300 | C40—C41 | 1.376 (12) |
C4—C5 | 1.365 (10) | C41—C42 | 1.383 (13) |
C5—C6 | 1.363 (11) | C41—H41 | 0.9300 |
C5—H5 | 0.9300 | C42—C43 | 1.367 (13) |
C6—H6 | 0.9300 | C42—H42 | 0.9300 |
C7—C8 | 1.445 (11) | C43—C44 | 1.355 (13) |
C7—H7 | 0.9300 | C43—H43 | 0.9300 |
C8—C13 | 1.394 (11) | C44—H44 | 0.9300 |
C8—C9 | 1.398 (11) | C45—C50 | 1.356 (10) |
C9—C10 | 1.379 (11) | C45—C46 | 1.386 (8) |
C10—C11 | 1.373 (12) | C46—C47 | 1.374 (12) |
C10—H10 | 0.9300 | C46—H46 | 0.9300 |
C11—C12 | 1.372 (13) | C47—C48 | 1.377 (8) |
C11—H11 | 0.9300 | C47—H47 | 0.9300 |
C12—C13 | 1.378 (12) | C48—C49 | 1.346 (12) |
C12—H12 | 0.9300 | C48—H48 | 0.9300 |
C13—H13 | 0.9300 | C49—C50 | 1.381 (8) |
C14—C19 | 1.376 (9) | C49—H49 | 0.9300 |
C14—C15 | 1.386 (7) | C50—H50 | 0.9300 |
C15—C16 | 1.370 (11) | C51—C56 | 1.378 (10) |
C15—H15 | 0.9300 | C51—C52 | 1.383 (10) |
C16—C17 | 1.376 (8) | C52—C53 | 1.385 (11) |
C16—H16 | 0.9300 | C52—H52 | 0.9300 |
C17—C18 | 1.314 (12) | C53—C54 | 1.348 (13) |
C17—H17 | 0.9300 | C53—H53 | 0.9300 |
C18—C19 | 1.377 (8) | C54—C55 | 1.363 (13) |
C18—H18 | 0.9300 | C54—H54 | 0.9300 |
C19—H19 | 0.9300 | C55—C56 | 1.380 (12) |
C20—C25 | 1.353 (10) | C55—H55 | 0.9300 |
C20—C21 | 1.382 (7) | C56—H56 | 0.9300 |
C21—C22 | 1.382 (11) | C57—C58 | 1.371 (7) |
C21—H21 | 0.9300 | C57—C62 | 1.375 (7) |
C22—C23 | 1.386 (8) | C58—C59 | 1.378 (11) |
C22—H22 | 0.9300 | C58—H58 | 0.9300 |
C23—C24 | 1.334 (13) | C59—C60 | 1.376 (8) |
C23—H23 | 0.9300 | C59—H59 | 0.9300 |
C24—C25 | 1.404 (8) | C60—C61 | 1.339 (12) |
C24—H24 | 0.9300 | C60—H60 | 0.9300 |
C25—H25 | 0.9300 | C61—C62 | 1.392 (8) |
C26—C31 | 1.367 (10) | C61—H61 | 0.9300 |
C26—C27 | 1.376 (9) | C62—H62 | 0.9300 |
C20—Sn1—C26 | 111.6 (3) | C30—C29—C28 | 118.6 (8) |
C20—Sn1—C14 | 112.9 (2) | C30—C29—H29 | 120.7 |
C26—Sn1—C14 | 111.1 (2) | C28—C29—H29 | 120.7 |
S1—Sn1—C14 | 107.92 (18) | C29—C30—C31 | 120.5 (8) |
S1—Sn1—C20 | 103.24 (19) | C29—C30—H30 | 119.8 |
S1—Sn1—C26 | 109.69 (18) | C31—C30—H30 | 119.8 |
Sn1—S1—C1 | 101.2 (2) | C26—C31—C30 | 121.6 (7) |
C51—Sn2—C45 | 114.2 (3) | C26—C31—H31 | 119.2 |
C51—Sn2—C57 | 111.1 (3) | C30—C31—H31 | 119.2 |
C45—Sn2—C57 | 112.0 (3) | C33—C32—C37 | 118.8 (8) |
S2—Sn2—C45 | 107.0 (2) | C33—C32—S2 | 119.8 (6) |
S2—Sn2—C51 | 102.5 (2) | C37—C32—S2 | 121.4 (6) |
S2—Sn2—C57 | 109.46 (18) | C32—C33—C34 | 120.7 (8) |
Sn2—S2—C32 | 101.1 (2) | C32—C33—H33 | 119.6 |
C7—N1—C4 | 121.3 (7) | C34—C33—H33 | 119.6 |
C38—N2—C35 | 122.5 (7) | C33—C34—C35 | 121.4 (8) |
C9—O1—H1 | 109.5 | C33—C34—H34 | 119.3 |
C40—O2—H2 | 109.5 | C35—C34—H34 | 119.3 |
C2—C1—C6 | 116.8 (7) | C36—C35—C34 | 117.8 (8) |
C2—C1—S1 | 122.5 (6) | C36—C35—N2 | 117.1 (7) |
C6—C1—S1 | 120.6 (6) | C34—C35—N2 | 125.1 (7) |
C3—C2—C1 | 121.9 (8) | C35—C36—C37 | 121.0 (8) |
C3—C2—H2A | 119.1 | C35—C36—H36 | 119.5 |
C1—C2—H2A | 119.1 | C37—C36—H36 | 119.5 |
C4—C3—C2 | 120.2 (7) | C32—C37—C36 | 120.2 (8) |
C4—C3—H3 | 119.9 | C32—C37—H37 | 119.9 |
C2—C3—H3 | 119.9 | C36—C37—H37 | 119.9 |
C5—C4—C3 | 118.5 (7) | N2—C38—C39 | 123.0 (7) |
C5—C4—N1 | 124.8 (7) | N2—C38—H38 | 118.5 |
C3—C4—N1 | 116.7 (7) | C39—C38—H38 | 118.5 |
C6—C5—C4 | 121.4 (8) | C44—C39—C40 | 118.0 (8) |
C6—C5—H5 | 119.3 | C44—C39—C38 | 120.6 (8) |
C4—C5—H5 | 119.3 | C40—C39—C38 | 121.4 (7) |
C5—C6—C1 | 121.2 (7) | O2—C40—C41 | 119.8 (8) |
C5—C6—H6 | 119.4 | O2—C40—C39 | 120.4 (8) |
C1—C6—H6 | 119.4 | C41—C40—C39 | 119.7 (8) |
N1—C7—C8 | 122.7 (8) | C40—C41—C42 | 120.0 (9) |
N1—C7—H7 | 118.6 | C40—C41—H41 | 120.0 |
C8—C7—H7 | 118.6 | C42—C41—H41 | 120.0 |
C13—C8—C9 | 118.0 (8) | C43—C42—C41 | 120.0 (9) |
C13—C8—C7 | 120.2 (8) | C43—C42—H42 | 120.0 |
C9—C8—C7 | 121.7 (7) | C41—C42—H42 | 120.0 |
O1—C9—C10 | 118.5 (8) | C44—C43—C42 | 120.5 (9) |
O1—C9—C8 | 121.0 (7) | C44—C43—H43 | 119.7 |
C10—C9—C8 | 120.4 (8) | C42—C43—H43 | 119.7 |
C11—C10—C9 | 119.3 (9) | C43—C44—C39 | 121.7 (9) |
C11—C10—H10 | 120.3 | C43—C44—H44 | 119.1 |
C9—C10—H10 | 120.3 | C39—C44—H44 | 119.1 |
C12—C11—C10 | 122.3 (9) | C50—C45—C46 | 117.9 (8) |
C12—C11—H11 | 118.9 | C50—C45—Sn2 | 123.3 (5) |
C10—C11—H11 | 118.9 | C46—C45—Sn2 | 118.9 (6) |
C11—C12—C13 | 118.0 (9) | C47—C46—C45 | 120.6 (9) |
C11—C12—H12 | 121.0 | C47—C46—H46 | 119.7 |
C13—C12—H12 | 121.0 | C45—C46—H46 | 119.7 |
C12—C13—C8 | 121.9 (9) | C46—C47—C48 | 120.0 (8) |
C12—C13—H13 | 119.1 | C46—C47—H47 | 120.0 |
C8—C13—H13 | 119.1 | C48—C47—H47 | 120.0 |
C19—C14—C15 | 118.0 (7) | C49—C48—C47 | 119.8 (8) |
C19—C14—Sn1 | 119.2 (5) | C49—C48—H48 | 120.1 |
C15—C14—Sn1 | 122.8 (5) | C47—C48—H48 | 120.1 |
C16—C15—C14 | 119.9 (7) | C48—C49—C50 | 119.8 (9) |
C16—C15—H15 | 120.1 | C48—C49—H49 | 120.1 |
C14—C15—H15 | 120.1 | C50—C49—H49 | 120.1 |
C15—C16—C17 | 120.9 (8) | C45—C50—C49 | 121.9 (8) |
C15—C16—H16 | 119.6 | C45—C50—H50 | 119.1 |
C17—C16—H16 | 119.6 | C49—C50—H50 | 119.1 |
C18—C17—C16 | 119.0 (8) | C56—C51—C52 | 118.8 (7) |
C18—C17—H17 | 120.5 | C56—C51—Sn2 | 120.1 (6) |
C16—C17—H17 | 120.5 | C52—C51—Sn2 | 121.0 (5) |
C17—C18—C19 | 122.1 (9) | C51—C52—C53 | 119.9 (8) |
C17—C18—H18 | 118.9 | C51—C52—H52 | 120.1 |
C19—C18—H18 | 118.9 | C53—C52—H52 | 120.1 |
C14—C19—C18 | 120.1 (8) | C54—C53—C52 | 121.2 (9) |
C14—C19—H19 | 120.0 | C54—C53—H53 | 119.4 |
C18—C19—H19 | 120.0 | C52—C53—H53 | 119.4 |
C25—C20—C21 | 118.7 (7) | C53—C54—C55 | 119.1 (9) |
C25—C20—Sn1 | 120.1 (5) | C53—C54—H54 | 120.5 |
C21—C20—Sn1 | 121.2 (6) | C55—C54—H54 | 120.5 |
C20—C21—C22 | 120.9 (8) | C54—C55—C56 | 121.3 (9) |
C20—C21—H21 | 119.5 | C54—C55—H55 | 119.3 |
C22—C21—H21 | 119.5 | C56—C55—H55 | 119.3 |
C21—C22—C23 | 119.0 (8) | C51—C56—C55 | 119.7 (8) |
C21—C22—H22 | 120.5 | C51—C56—H56 | 120.1 |
C23—C22—H22 | 120.5 | C55—C56—H56 | 120.1 |
C24—C23—C22 | 120.4 (8) | C58—C57—C62 | 117.6 (7) |
C24—C23—H23 | 119.8 | C58—C57—Sn2 | 117.9 (5) |
C22—C23—H23 | 119.8 | C62—C57—Sn2 | 124.5 (5) |
C23—C24—C25 | 120.3 (9) | C57—C58—C59 | 121.4 (7) |
C23—C24—H24 | 119.9 | C57—C58—H58 | 119.3 |
C25—C24—H24 | 119.9 | C59—C58—H58 | 119.3 |
C20—C25—C24 | 120.6 (8) | C60—C59—C58 | 120.4 (9) |
C20—C25—H25 | 119.7 | C60—C59—H59 | 119.8 |
C24—C25—H25 | 119.7 | C58—C59—H59 | 119.8 |
C31—C26—C27 | 117.2 (7) | C61—C60—C59 | 118.9 (9) |
C31—C26—Sn1 | 119.0 (5) | C61—C60—H60 | 120.6 |
C27—C26—Sn1 | 123.8 (5) | C59—C60—H60 | 120.6 |
C28—C27—C26 | 121.0 (7) | C60—C61—C62 | 121.1 (8) |
C28—C27—H27 | 119.5 | C60—C61—H61 | 119.4 |
C26—C27—H27 | 119.5 | C62—C61—H61 | 119.4 |
C29—C28—C27 | 121.0 (7) | C57—C62—C61 | 120.7 (8) |
C29—C28—H28 | 119.5 | C57—C62—H62 | 119.7 |
C27—C28—H28 | 119.5 | C61—C62—H62 | 119.7 |
C20—Sn1—S1—C1 | −170.2 (3) | C27—C26—C31—C30 | 1.7 (12) |
C26—Sn1—S1—C1 | 70.7 (3) | Sn1—C26—C31—C30 | −175.7 (7) |
C14—Sn1—S1—C1 | −50.5 (3) | C29—C30—C31—C26 | −3.7 (14) |
C51—Sn2—S2—C32 | −169.5 (3) | Sn2—S2—C32—C33 | 105.7 (7) |
C45—Sn2—S2—C32 | −49.1 (4) | Sn2—S2—C32—C37 | −74.3 (7) |
C57—Sn2—S2—C32 | 72.4 (4) | C37—C32—C33—C34 | −1.9 (13) |
Sn1—S1—C1—C2 | −73.9 (6) | S2—C32—C33—C34 | 178.1 (7) |
Sn1—S1—C1—C6 | 108.2 (6) | C32—C33—C34—C35 | 1.6 (14) |
C6—C1—C2—C3 | −0.3 (11) | C33—C34—C35—C36 | 0.4 (13) |
S1—C1—C2—C3 | −178.2 (6) | C33—C34—C35—N2 | 178.8 (8) |
C1—C2—C3—C4 | 1.7 (12) | C38—N2—C35—C36 | −152.0 (7) |
C2—C3—C4—C5 | −1.8 (11) | C38—N2—C35—C34 | 29.6 (12) |
C2—C3—C4—N1 | 179.8 (7) | C34—C35—C36—C37 | −2.0 (12) |
C7—N1—C4—C5 | 27.7 (11) | N2—C35—C36—C37 | 179.5 (7) |
C7—N1—C4—C3 | −154.0 (7) | C33—C32—C37—C36 | 0.4 (12) |
C3—C4—C5—C6 | 0.5 (11) | S2—C32—C37—C36 | −179.6 (6) |
N1—C4—C5—C6 | 178.8 (7) | C35—C36—C37—C32 | 1.6 (12) |
C4—C5—C6—C1 | 0.8 (12) | C35—N2—C38—C39 | −179.1 (7) |
C2—C1—C6—C5 | −0.9 (11) | N2—C38—C39—C44 | −179.0 (8) |
S1—C1—C6—C5 | 177.0 (6) | N2—C38—C39—C40 | 2.0 (12) |
C4—N1—C7—C8 | −177.4 (6) | C44—C39—C40—O2 | −179.1 (8) |
N1—C7—C8—C13 | −176.0 (7) | C38—C39—C40—O2 | −0.1 (12) |
N1—C7—C8—C9 | 1.1 (12) | C44—C39—C40—C41 | 1.0 (13) |
C13—C8—C9—O1 | 179.6 (7) | C38—C39—C40—C41 | 180.0 (8) |
C7—C8—C9—O1 | 2.4 (12) | O2—C40—C41—C42 | −179.8 (8) |
C13—C8—C9—C10 | −1.8 (12) | C39—C40—C41—C42 | 0.1 (14) |
C7—C8—C9—C10 | −178.9 (8) | C40—C41—C42—C43 | −0.6 (15) |
O1—C9—C10—C11 | 179.4 (8) | C41—C42—C43—C44 | −0.1 (15) |
C8—C9—C10—C11 | 0.7 (13) | C42—C43—C44—C39 | 1.2 (16) |
C9—C10—C11—C12 | 0.5 (14) | C40—C39—C44—C43 | −1.7 (14) |
C10—C11—C12—C13 | −0.6 (14) | C38—C39—C44—C43 | 179.3 (9) |
C11—C12—C13—C8 | −0.6 (14) | C51—Sn2—C45—C50 | 172.4 (7) |
C9—C8—C13—C12 | 1.7 (12) | C57—Sn2—C45—C50 | −60.2 (7) |
C7—C8—C13—C12 | 178.9 (8) | S2—Sn2—C45—C50 | 59.7 (7) |
C20—Sn1—C14—C19 | −5.1 (6) | C51—Sn2—C45—C46 | −6.4 (7) |
C26—Sn1—C14—C19 | 121.1 (6) | C57—Sn2—C45—C46 | 121.0 (6) |
S1—Sn1—C14—C19 | −118.6 (5) | S2—Sn2—C45—C46 | −119.1 (6) |
C20—Sn1—C14—C15 | 174.1 (6) | C50—C45—C46—C47 | −1.8 (13) |
C26—Sn1—C14—C15 | −59.6 (7) | Sn2—C45—C46—C47 | 177.0 (7) |
S1—Sn1—C14—C15 | 60.7 (6) | C45—C46—C47—C48 | 2.1 (14) |
C19—C14—C15—C16 | 1.7 (12) | C46—C47—C48—C49 | −1.5 (14) |
Sn1—C14—C15—C16 | −177.6 (6) | C47—C48—C49—C50 | 0.5 (15) |
C14—C15—C16—C17 | −2.7 (14) | C46—C45—C50—C49 | 0.9 (13) |
C15—C16—C17—C18 | 1.8 (15) | Sn2—C45—C50—C49 | −177.9 (7) |
C16—C17—C18—C19 | 0.2 (15) | C48—C49—C50—C45 | −0.2 (15) |
C15—C14—C19—C18 | 0.2 (11) | C45—Sn2—C51—C56 | 105.5 (6) |
Sn1—C14—C19—C18 | 179.5 (6) | C57—Sn2—C51—C56 | −22.4 (7) |
C17—C18—C19—C14 | −1.2 (14) | S2—Sn2—C51—C56 | −139.2 (6) |
C26—Sn1—C20—C25 | −25.1 (7) | C45—Sn2—C51—C52 | −78.8 (7) |
C14—Sn1—C20—C25 | 100.9 (6) | C57—Sn2—C51—C52 | 153.4 (6) |
S1—Sn1—C20—C25 | −142.8 (6) | S2—Sn2—C51—C52 | 36.5 (6) |
C26—Sn1—C20—C21 | 155.8 (6) | C56—C51—C52—C53 | −1.1 (12) |
C14—Sn1—C20—C21 | −78.2 (6) | Sn2—C51—C52—C53 | −176.9 (6) |
S1—Sn1—C20—C21 | 38.1 (6) | C51—C52—C53—C54 | 0.6 (14) |
C25—C20—C21—C22 | 2.3 (12) | C52—C53—C54—C55 | 0.5 (15) |
Sn1—C20—C21—C22 | −178.6 (6) | C53—C54—C55—C56 | −1.0 (15) |
C20—C21—C22—C23 | −1.4 (13) | C52—C51—C56—C55 | 0.6 (12) |
C21—C22—C23—C24 | 0.1 (14) | Sn2—C51—C56—C55 | 176.4 (7) |
C22—C23—C24—C25 | 0.3 (15) | C54—C55—C56—C51 | 0.5 (14) |
C21—C20—C25—C24 | −1.9 (12) | C51—Sn2—C57—C58 | 92.6 (7) |
Sn1—C20—C25—C24 | 179.0 (7) | C45—Sn2—C57—C58 | −36.4 (7) |
C23—C24—C25—C20 | 0.6 (14) | S2—Sn2—C57—C58 | −154.9 (6) |
C20—Sn1—C26—C31 | 95.4 (6) | C51—Sn2—C57—C62 | −85.1 (7) |
C14—Sn1—C26—C31 | −31.6 (7) | C45—Sn2—C57—C62 | 145.9 (7) |
S1—Sn1—C26—C31 | −150.8 (6) | S2—Sn2—C57—C62 | 27.4 (8) |
C20—Sn1—C26—C27 | −81.8 (6) | C62—C57—C58—C59 | −1.0 (14) |
C14—Sn1—C26—C27 | 151.3 (6) | Sn2—C57—C58—C59 | −178.8 (7) |
S1—Sn1—C26—C27 | 32.0 (6) | C57—C58—C59—C60 | 1.4 (15) |
C31—C26—C27—C28 | 0.1 (11) | C58—C59—C60—C61 | −2.2 (16) |
Sn1—C26—C27—C28 | 177.4 (6) | C59—C60—C61—C62 | 2.5 (16) |
C26—C27—C28—C29 | 0.0 (13) | C58—C57—C62—C61 | 1.3 (13) |
C27—C28—C29—C30 | −1.9 (13) | Sn2—C57—C62—C61 | 178.9 (7) |
C28—C29—C30—C31 | 3.7 (14) | C60—C61—C62—C57 | −2.1 (16) |
Experimental details
Crystal data | |
Chemical formula | [Sn(C6H5)3(C13H10NOS)] |
Mr | 578.27 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 9.5561 (10), 9.6073 (11), 30.110 (3) |
α, β, γ (°) | 92.064 (2), 95.430 (2), 104.936 (3) |
V (Å3) | 2653.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.07 |
Crystal size (mm) | 0.15 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.857, 0.901 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13756, 9194, 6702 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.142, 1.00 |
No. of reflections | 9194 |
No. of parameters | 631 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + 13.8664P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.58, −1.26 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
Sn1—S1 | 2.421 (2) | Sn2—S2 | 2.423 (2) |
Sn1—C14 | 2.124 (6) | Sn2—C45 | 2.127 (7) |
Sn1—C20 | 2.113 (7) | Sn2—C51 | 2.120 (7) |
Sn1—C26 | 2.120 (7) | Sn2—C57 | 2.129 (7) |
S1—Sn1—C14 | 107.92 (18) | S2—Sn2—C45 | 107.0 (2) |
S1—Sn1—C20 | 103.24 (19) | S2—Sn2—C51 | 102.5 (2) |
S1—Sn1—C26 | 109.69 (18) | S2—Sn2—C57 | 109.46 (18) |
Sn1—S1—C1 | 101.2 (2) | Sn2—S2—C32 | 101.1 (2) |
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Recently, a number of Schiff-bases have been investigated in terms of their crystallography and coordination chemistry (Garnovski et al., 1993). During the last decade, Schiff-base complexes have been applied in catalytic reactions and biological systems (Anderson et al., 1997). Organotin complexes containing Schiff-bases have attracted much attention owing to their potential biological activities (Nath et al., 1997). The title compound (I) was synthesized and its crystal structure determined (Fig. 1 and Table 1). Two independent molecules comprise the crystallographic asymmetric unit. In each of these, the central tin atom exists in a distorted tetrahedron defined by a C3S donor set. The geometric parameters are in good agreement with those found in (4,5-diphenyl-4-oxazoline-2-thiolato)triphenyltin (Li et al., 2007). The mean planes of the two benzene rings in (I) make a dihedral angle of 31.0 (5)° (molecule 1) and 31.3 (6)° (molecule 2) showing that the Schiff-base ligand adopts a non-planar conformation in each case.