Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807024543/hb2424sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807024543/hb2424Isup2.hkl |
CCDC reference: 650569
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.039
- wR factor = 0.101
- Data-to-parameter ratio = 21.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.50 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.51 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C21 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C30 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C31 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 7 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 structures, see: Tian et al. (2004, 2006); Tian, Sun, Yang & Ng (2005); Tian, Sun, Yang & Yang (2005).
For related literature, see: Chandrasekhar et al. (2002); Gielen et al. (2005).
Bis[tris(2-methyl-2-phenylpropyl)tin] oxide (1.05 g, 1 mmol) and fumaric acid (0.12 g, 1 mmol) in toluene (50 ml) were refluxed for 3 h with azeotropic removal of water via a Dean-Stark trap. The resulting clear solution was evaporated under reduced pressure. The white solid obtained was purified by recrystallization from methanol, and crystals of (I) were obtained from a chloroform-hexane (1:1, v/v) solution by slow evaporation at 298 K (yield 83%, m.p. 422–423 K). Analysis, found: C 66.56, H 6.89%; calculated for C64H80O4Sn2: C 66.80, H 7.01%.
The H atoms were placed at calculated positions (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
The structural chemistry of organotin carboxylates continues to receive attention owing to their biological properties, especially their antitumour activities (Chandrasekhar et al., 2002; Gielen et al., 2005). Recently, we have reported several tris(2-methyl-2-phenylpropyl)tin carboxylates, such as bis[tris(2-methyl-2-phenylpropyl)tin(IV)] 3,4,5,6-tetrafluorophthalate (Tian et al., 2004), bis[tris(2-methyl-2-phenylpropyl)tin(IV)] phthalate (Tian, Sun, Yang & Ng, 2005), tris(2-methyl-2-phenylpropyl)tin pyridine-3-carboxylate (Tian, Sun, Yang & Yang, 2005) and tris(2-methyl-2-phenylpropyl)tin 2-phthalimidoacetate (Tian et al., 2006), which all possess a distorted tetrahedral geometry. In the title compound, (I), tetrahedral coordination is also observed (Fig. 1 & Table 1). The Sn···O2 separation of 3.072 (4)Å indicates there is a weak interaction between these atoms, which distorts the tetrahedral geometry. The three Sn—C distances are almost identical. The Sn—O bond length in (I) is similar to that found in the carboxylate structures mentioned above.
For related structures, see: Tian et al. (2004, 2006); Tian, Sun, Yang & Ng (2005); Tian, Sun, Yang & Yang (2005).
For related literature, see: Chandrasekhar et al. (2002); Gielen et al. (2005).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The structure of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity. |
[Sn2(C10H13)6(C4H2O4)] | F(000) = 1192 |
Mr = 1150.66 | Dx = 1.294 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4827 reflections |
a = 9.6017 (9) Å | θ = 2.5–22.3° |
b = 18.6352 (18) Å | µ = 0.89 mm−1 |
c = 16.5097 (16) Å | T = 295 K |
β = 91.985 (1)° | Prism, colourless |
V = 2952.3 (5) Å3 | 0.22 × 0.10 × 0.08 mm |
Z = 2 |
Bruker SMART APEX CCD area-detector diffractometer | 6102 independent reflections |
Radiation source: fine-focus sealed tube | 4565 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
φ and ω scans | θmax = 26.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −12→12 |
Tmin = 0.828, Tmax = 0.932 | k = −23→22 |
23553 measured reflections | l = −20→20 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0466P)2 + 0.84P] where P = (Fo2 + 2Fc2)/3 |
6102 reflections | (Δ/σ)max = 0.002 |
286 parameters | Δρmax = 0.67 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
[Sn2(C10H13)6(C4H2O4)] | V = 2952.3 (5) Å3 |
Mr = 1150.66 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.6017 (9) Å | µ = 0.89 mm−1 |
b = 18.6352 (18) Å | T = 295 K |
c = 16.5097 (16) Å | 0.22 × 0.10 × 0.08 mm |
β = 91.985 (1)° |
Bruker SMART APEX CCD area-detector diffractometer | 6102 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 4565 reflections with I > 2σ(I) |
Tmin = 0.828, Tmax = 0.932 | Rint = 0.048 |
23553 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.67 e Å−3 |
6102 reflections | Δρmin = −0.40 e Å−3 |
286 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 | ||
Sn1 | 0.26662 (2) | 0.875316 (12) | 0.183016 (13) | 0.03679 (9) | |
O1 | 0.1351 (3) | 0.93708 (15) | 0.10958 (16) | 0.0591 (7) | |
O2 | 0.1864 (5) | 0.87575 (19) | 0.0013 (2) | 0.1071 (14) | |
C1 | 0.1220 (5) | 0.9236 (2) | 0.0345 (3) | 0.0626 (11) | |
C2 | 0.0287 (4) | 0.9720 (2) | −0.0139 (2) | 0.0552 (10) | |
H2 | 0.0110 | 0.9606 | −0.0681 | 0.066* | |
C3 | 0.4650 (4) | 0.89136 (19) | 0.1303 (2) | 0.0457 (9) | |
H3A | 0.5190 | 0.8477 | 0.1378 | 0.055* | |
H3B | 0.4496 | 0.8981 | 0.0725 | 0.055* | |
C4 | 0.5541 (4) | 0.9550 (2) | 0.1633 (2) | 0.0474 (9) | |
C5 | 0.4787 (5) | 1.0247 (2) | 0.1402 (3) | 0.0760 (14) | |
H5A | 0.3932 | 1.0276 | 0.1685 | 0.114* | |
H5B | 0.4587 | 1.0253 | 0.0828 | 0.114* | |
H5C | 0.5369 | 1.0648 | 0.1548 | 0.114* | |
C6 | 0.6948 (4) | 0.9532 (3) | 0.1223 (3) | 0.0793 (14) | |
H6A | 0.7515 | 0.9924 | 0.1419 | 0.119* | |
H6B | 0.6800 | 0.9575 | 0.0647 | 0.119* | |
H6C | 0.7410 | 0.9086 | 0.1346 | 0.119* | |
C7 | 0.5821 (3) | 0.94903 (13) | 0.25515 (11) | 0.0463 (9) | |
C8 | 0.6025 (3) | 1.01064 (11) | 0.30152 (17) | 0.0678 (12) | |
H8 | 0.5989 | 1.0555 | 0.2769 | 0.081* | |
C9 | 0.6283 (3) | 1.00515 (16) | 0.38465 (16) | 0.0858 (16) | |
H9 | 0.6420 | 1.0464 | 0.4157 | 0.103* | |
C10 | 0.6338 (3) | 0.9381 (2) | 0.42142 (11) | 0.0814 (15) | |
H10 | 0.6511 | 0.9344 | 0.4770 | 0.098* | |
C11 | 0.6134 (3) | 0.87645 (15) | 0.37504 (16) | 0.0726 (13) | |
H11 | 0.6171 | 0.8316 | 0.3996 | 0.087* | |
C12 | 0.5876 (3) | 0.88194 (11) | 0.29191 (16) | 0.0578 (10) | |
H12 | 0.5740 | 0.8407 | 0.2609 | 0.069* | |
C13 | 0.1789 (4) | 0.7698 (2) | 0.1786 (2) | 0.0561 (10) | |
H13A | 0.1544 | 0.7571 | 0.2333 | 0.067* | |
H13B | 0.0924 | 0.7725 | 0.1465 | 0.067* | |
C14 | 0.2641 (5) | 0.7068 (2) | 0.1450 (2) | 0.0586 (11) | |
C15 | 0.2827 (5) | 0.7185 (2) | 0.0543 (2) | 0.0705 (13) | |
H15A | 0.3296 | 0.7633 | 0.0461 | 0.106* | |
H15B | 0.1930 | 0.7195 | 0.0268 | 0.106* | |
H15C | 0.3371 | 0.6800 | 0.0332 | 0.106* | |
C16 | 0.1767 (7) | 0.6383 (2) | 0.1551 (4) | 0.0941 (18) | |
H16A | 0.2246 | 0.5982 | 0.1325 | 0.141* | |
H16B | 0.0878 | 0.6441 | 0.1275 | 0.141* | |
H16C | 0.1632 | 0.6299 | 0.2117 | 0.141* | |
C17 | 0.4028 (3) | 0.69769 (16) | 0.19162 (18) | 0.0671 (12) | |
C18 | 0.4029 (4) | 0.69271 (18) | 0.27563 (19) | 0.0906 (17) | |
H18 | 0.3196 | 0.6961 | 0.3025 | 0.109* | |
C19 | 0.5275 (6) | 0.6826 (2) | 0.31953 (18) | 0.128 (3) | |
H19 | 0.5276 | 0.6793 | 0.3757 | 0.154* | |
C20 | 0.6521 (4) | 0.6776 (2) | 0.2794 (3) | 0.143 (3) | |
H20 | 0.7354 | 0.6708 | 0.3088 | 0.172* | |
C21 | 0.6520 (3) | 0.6825 (2) | 0.1954 (3) | 0.134 (3) | |
H21 | 0.7353 | 0.6791 | 0.1686 | 0.161* | |
C22 | 0.5274 (4) | 0.69260 (18) | 0.15152 (19) | 0.0906 (16) | |
H22 | 0.5273 | 0.6959 | 0.0953 | 0.109* | |
C23 | 0.2213 (4) | 0.9367 (2) | 0.2888 (2) | 0.0487 (9) | |
H23A | 0.3047 | 0.9374 | 0.3237 | 0.058* | |
H23B | 0.2033 | 0.9857 | 0.2718 | 0.058* | |
C24 | 0.0987 (4) | 0.9124 (2) | 0.3405 (2) | 0.0580 (11) | |
C25 | 0.0768 (5) | 0.9691 (3) | 0.4075 (3) | 0.0903 (17) | |
H25A | 0.0043 | 0.9533 | 0.4419 | 0.135* | |
H25B | 0.0507 | 1.0140 | 0.3829 | 0.135* | |
H25C | 0.1618 | 0.9751 | 0.4391 | 0.135* | |
C26 | −0.0320 (4) | 0.9098 (3) | 0.2859 (3) | 0.0937 (17) | |
H26A | −0.0236 | 0.8718 | 0.2471 | 0.141* | |
H26B | −0.0433 | 0.9547 | 0.2580 | 0.141* | |
H26C | −0.1116 | 0.9011 | 0.3182 | 0.141* | |
C27 | 0.1309 (4) | 0.84148 (16) | 0.38337 (18) | 0.0645 (12) | |
C28 | 0.2573 (3) | 0.8341 (2) | 0.4262 (2) | 0.0865 (15) | |
H28 | 0.3213 | 0.8715 | 0.4272 | 0.104* | |
C29 | 0.2879 (5) | 0.7707 (3) | 0.4675 (2) | 0.137 (3) | |
H29 | 0.3724 | 0.7657 | 0.4962 | 0.165* | |
C30 | 0.1921 (7) | 0.71473 (19) | 0.4660 (3) | 0.161 (4) | |
H30 | 0.2126 | 0.6723 | 0.4936 | 0.193* | |
C31 | 0.0657 (6) | 0.72215 (18) | 0.4231 (3) | 0.147 (4) | |
H31 | 0.0016 | 0.6847 | 0.4221 | 0.177* | |
C32 | 0.0351 (4) | 0.7855 (2) | 0.3818 (2) | 0.099 (2) | |
H32 | −0.0494 | 0.7905 | 0.3532 | 0.119* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.04145 (15) | 0.03912 (14) | 0.02958 (13) | 0.00480 (10) | −0.00185 (9) | −0.00045 (10) |
O1 | 0.0569 (16) | 0.0752 (19) | 0.0443 (16) | 0.0170 (14) | −0.0124 (13) | 0.0083 (14) |
O2 | 0.154 (4) | 0.100 (3) | 0.065 (2) | 0.063 (3) | −0.035 (2) | −0.0122 (19) |
C1 | 0.070 (3) | 0.064 (3) | 0.053 (3) | 0.012 (2) | −0.013 (2) | 0.002 (2) |
C2 | 0.059 (3) | 0.064 (3) | 0.042 (2) | 0.005 (2) | −0.0093 (18) | 0.0083 (19) |
C3 | 0.044 (2) | 0.053 (2) | 0.041 (2) | 0.0044 (16) | 0.0028 (16) | −0.0011 (16) |
C4 | 0.053 (2) | 0.052 (2) | 0.038 (2) | −0.0074 (18) | −0.0001 (17) | 0.0064 (16) |
C5 | 0.107 (4) | 0.056 (3) | 0.063 (3) | −0.010 (3) | −0.025 (3) | 0.019 (2) |
C6 | 0.063 (3) | 0.122 (4) | 0.054 (3) | −0.029 (3) | 0.012 (2) | 0.003 (3) |
C7 | 0.0359 (19) | 0.059 (2) | 0.045 (2) | −0.0005 (17) | 0.0035 (16) | 0.0058 (17) |
C8 | 0.083 (3) | 0.061 (3) | 0.059 (3) | 0.001 (2) | −0.006 (2) | −0.004 (2) |
C9 | 0.103 (4) | 0.100 (4) | 0.052 (3) | 0.014 (3) | −0.015 (3) | −0.019 (3) |
C10 | 0.066 (3) | 0.137 (5) | 0.040 (2) | 0.005 (3) | −0.007 (2) | 0.009 (3) |
C11 | 0.060 (3) | 0.099 (4) | 0.058 (3) | −0.006 (3) | −0.011 (2) | 0.031 (3) |
C12 | 0.050 (2) | 0.066 (3) | 0.057 (2) | −0.005 (2) | −0.0041 (19) | 0.014 (2) |
C13 | 0.066 (3) | 0.050 (2) | 0.052 (2) | −0.012 (2) | 0.010 (2) | −0.0066 (18) |
C14 | 0.093 (3) | 0.039 (2) | 0.045 (2) | −0.002 (2) | 0.012 (2) | −0.0017 (17) |
C15 | 0.102 (4) | 0.062 (3) | 0.047 (2) | 0.008 (3) | 0.003 (2) | −0.013 (2) |
C16 | 0.139 (5) | 0.048 (3) | 0.096 (4) | −0.025 (3) | 0.012 (4) | −0.007 (3) |
C17 | 0.107 (4) | 0.038 (2) | 0.056 (3) | 0.013 (2) | 0.005 (3) | −0.0013 (19) |
C18 | 0.138 (5) | 0.077 (3) | 0.056 (3) | 0.012 (3) | −0.007 (3) | 0.015 (3) |
C19 | 0.197 (8) | 0.087 (4) | 0.096 (5) | 0.025 (5) | −0.053 (5) | 0.010 (4) |
C20 | 0.156 (7) | 0.100 (5) | 0.169 (8) | 0.060 (5) | −0.077 (6) | −0.004 (5) |
C21 | 0.128 (6) | 0.117 (6) | 0.156 (7) | 0.054 (5) | −0.019 (5) | −0.007 (5) |
C22 | 0.104 (4) | 0.080 (4) | 0.087 (4) | 0.037 (3) | −0.004 (3) | 0.002 (3) |
C23 | 0.054 (2) | 0.053 (2) | 0.039 (2) | 0.0036 (18) | 0.0033 (17) | −0.0132 (17) |
C24 | 0.045 (2) | 0.078 (3) | 0.052 (2) | −0.002 (2) | 0.0084 (18) | −0.026 (2) |
C25 | 0.099 (4) | 0.098 (4) | 0.076 (3) | 0.007 (3) | 0.029 (3) | −0.042 (3) |
C26 | 0.040 (2) | 0.154 (5) | 0.087 (4) | 0.010 (3) | 0.007 (2) | −0.030 (4) |
C27 | 0.073 (3) | 0.075 (3) | 0.047 (2) | −0.021 (3) | 0.031 (2) | −0.017 (2) |
C28 | 0.093 (4) | 0.098 (4) | 0.069 (3) | 0.007 (3) | 0.016 (3) | 0.021 (3) |
C29 | 0.183 (8) | 0.148 (7) | 0.083 (4) | 0.035 (6) | 0.038 (5) | 0.043 (5) |
C30 | 0.288 (13) | 0.109 (6) | 0.091 (5) | 0.019 (7) | 0.092 (7) | 0.033 (5) |
C31 | 0.238 (11) | 0.104 (6) | 0.106 (6) | −0.060 (6) | 0.099 (7) | −0.021 (5) |
C32 | 0.122 (5) | 0.104 (4) | 0.075 (4) | −0.042 (4) | 0.055 (3) | −0.025 (3) |
Sn1—O1 | 2.070 (2) | C15—H15B | 0.9600 |
Sn1—C13 | 2.140 (4) | C15—H15C | 0.9600 |
Sn1—C3 | 2.142 (4) | C16—H16A | 0.9600 |
Sn1—C23 | 2.145 (3) | C16—H16B | 0.9600 |
O1—C1 | 1.267 (5) | C16—H16C | 0.9600 |
O2—C1 | 1.225 (5) | C17—C18 | 1.3900 |
C1—C2 | 1.485 (5) | C17—C22 | 1.3900 |
C2—C2i | 1.273 (7) | C18—C19 | 1.3900 |
C2—H2 | 0.9300 | C18—H18 | 0.9300 |
C3—C4 | 1.549 (5) | C19—C20 | 1.3900 |
C3—H3A | 0.9700 | C19—H19 | 0.9300 |
C3—H3B | 0.9700 | C20—C21 | 1.3900 |
C4—C5 | 1.529 (5) | C20—H20 | 0.9300 |
C4—C6 | 1.532 (5) | C21—C22 | 1.3900 |
C4—C7 | 1.535 (4) | C21—H21 | 0.9300 |
C5—H5A | 0.9600 | C22—H22 | 0.9300 |
C5—H5B | 0.9600 | C23—C24 | 1.545 (5) |
C5—H5C | 0.9600 | C23—H23A | 0.9700 |
C6—H6A | 0.9600 | C23—H23B | 0.9700 |
C6—H6B | 0.9600 | C24—C26 | 1.521 (6) |
C6—H6C | 0.9600 | C24—C27 | 1.526 (5) |
C7—C8 | 1.3900 | C24—C25 | 1.548 (5) |
C7—C12 | 1.3900 | C25—H25A | 0.9600 |
C8—C9 | 1.3900 | C25—H25B | 0.9600 |
C8—H8 | 0.9300 | C25—H25C | 0.9600 |
C9—C10 | 1.3900 | C26—H26A | 0.9600 |
C9—H9 | 0.9300 | C26—H26B | 0.9600 |
C10—C11 | 1.3900 | C26—H26C | 0.9600 |
C10—H10 | 0.9300 | C27—C28 | 1.3900 |
C11—C12 | 1.3900 | C27—C32 | 1.3900 |
C11—H11 | 0.9300 | C28—C29 | 1.3900 |
C12—H12 | 0.9300 | C28—H28 | 0.9300 |
C13—C14 | 1.544 (5) | C29—C30 | 1.3900 |
C13—H13A | 0.9700 | C29—H29 | 0.9300 |
C13—H13B | 0.9700 | C30—C31 | 1.3900 |
C14—C17 | 1.525 (5) | C30—H30 | 0.9300 |
C14—C15 | 1.529 (5) | C31—C32 | 1.3900 |
C14—C16 | 1.540 (6) | C31—H31 | 0.9300 |
C15—H15A | 0.9600 | C32—H32 | 0.9300 |
O1—Sn1—C13 | 105.04 (14) | C14—C15—H15C | 109.5 |
O1—Sn1—C3 | 102.57 (13) | H15A—C15—H15C | 109.5 |
C13—Sn1—C3 | 117.96 (14) | H15B—C15—H15C | 109.5 |
O1—Sn1—C23 | 92.50 (13) | C14—C16—H16A | 109.5 |
C13—Sn1—C23 | 115.29 (14) | C14—C16—H16B | 109.5 |
C3—Sn1—C23 | 117.68 (14) | H16A—C16—H16B | 109.5 |
C1—O1—Sn1 | 120.0 (3) | C14—C16—H16C | 109.5 |
O2—C1—O1 | 123.2 (4) | H16A—C16—H16C | 109.5 |
O2—C1—C2 | 120.4 (4) | H16B—C16—H16C | 109.5 |
O1—C1—C2 | 116.3 (4) | C18—C17—C22 | 120.0 |
C2i—C2—C1 | 124.4 (5) | C18—C17—C14 | 118.8 (3) |
C2i—C2—H2 | 117.8 | C22—C17—C14 | 121.2 (3) |
C1—C2—H2 | 117.8 | C19—C18—C17 | 120.0 |
C4—C3—Sn1 | 116.9 (2) | C19—C18—H18 | 120.0 |
C4—C3—H3A | 108.1 | C17—C18—H18 | 120.0 |
Sn1—C3—H3A | 108.1 | C18—C19—C20 | 120.0 |
C4—C3—H3B | 108.1 | C18—C19—H19 | 120.0 |
Sn1—C3—H3B | 108.1 | C20—C19—H19 | 120.0 |
H3A—C3—H3B | 107.3 | C21—C20—C19 | 120.0 |
C5—C4—C6 | 109.0 (3) | C21—C20—H20 | 120.0 |
C5—C4—C7 | 111.9 (3) | C19—C20—H20 | 120.0 |
C6—C4—C7 | 107.9 (3) | C20—C21—C22 | 120.0 |
C5—C4—C3 | 108.2 (3) | C20—C21—H21 | 120.0 |
C6—C4—C3 | 108.2 (3) | C22—C21—H21 | 120.0 |
C7—C4—C3 | 111.6 (3) | C21—C22—C17 | 120.0 |
C4—C5—H5A | 109.5 | C21—C22—H22 | 120.0 |
C4—C5—H5B | 109.5 | C17—C22—H22 | 120.0 |
H5A—C5—H5B | 109.5 | C24—C23—Sn1 | 118.3 (2) |
C4—C5—H5C | 109.5 | C24—C23—H23A | 107.7 |
H5A—C5—H5C | 109.5 | Sn1—C23—H23A | 107.7 |
H5B—C5—H5C | 109.5 | C24—C23—H23B | 107.7 |
C4—C6—H6A | 109.5 | Sn1—C23—H23B | 107.7 |
C4—C6—H6B | 109.5 | H23A—C23—H23B | 107.1 |
H6A—C6—H6B | 109.5 | C26—C24—C27 | 113.3 (4) |
C4—C6—H6C | 109.5 | C26—C24—C23 | 108.1 (4) |
H6A—C6—H6C | 109.5 | C27—C24—C23 | 111.3 (3) |
H6B—C6—H6C | 109.5 | C26—C24—C25 | 108.4 (4) |
C8—C7—C12 | 120.0 | C27—C24—C25 | 106.9 (3) |
C8—C7—C4 | 120.1 (2) | C23—C24—C25 | 108.7 (3) |
C12—C7—C4 | 119.9 (2) | C24—C25—H25A | 109.5 |
C7—C8—C9 | 120.0 | C24—C25—H25B | 109.5 |
C7—C8—H8 | 120.0 | H25A—C25—H25B | 109.5 |
C9—C8—H8 | 120.0 | C24—C25—H25C | 109.5 |
C8—C9—C10 | 120.0 | H25A—C25—H25C | 109.5 |
C8—C9—H9 | 120.0 | H25B—C25—H25C | 109.5 |
C10—C9—H9 | 120.0 | C24—C26—H26A | 109.5 |
C11—C10—C9 | 120.0 | C24—C26—H26B | 109.5 |
C11—C10—H10 | 120.0 | H26A—C26—H26B | 109.5 |
C9—C10—H10 | 120.0 | C24—C26—H26C | 109.5 |
C12—C11—C10 | 120.0 | H26A—C26—H26C | 109.5 |
C12—C11—H11 | 120.0 | H26B—C26—H26C | 109.5 |
C10—C11—H11 | 120.0 | C28—C27—C32 | 120.0 |
C11—C12—C7 | 120.0 | C28—C27—C24 | 118.7 (3) |
C11—C12—H12 | 120.0 | C32—C27—C24 | 121.2 (3) |
C7—C12—H12 | 120.0 | C29—C28—C27 | 120.0 |
C14—C13—Sn1 | 119.9 (3) | C29—C28—H28 | 120.0 |
C14—C13—H13A | 107.4 | C27—C28—H28 | 120.0 |
Sn1—C13—H13A | 107.4 | C30—C29—C28 | 120.0 |
C14—C13—H13B | 107.4 | C30—C29—H29 | 120.0 |
Sn1—C13—H13B | 107.4 | C28—C29—H29 | 120.0 |
H13A—C13—H13B | 106.9 | C29—C30—C31 | 120.0 |
C17—C14—C15 | 112.4 (4) | C29—C30—H30 | 120.0 |
C17—C14—C16 | 108.8 (4) | C31—C30—H30 | 120.0 |
C15—C14—C16 | 107.9 (4) | C30—C31—C32 | 120.0 |
C17—C14—C13 | 111.6 (3) | C30—C31—H31 | 120.0 |
C15—C14—C13 | 108.9 (3) | C32—C31—H31 | 120.0 |
C16—C14—C13 | 107.1 (4) | C31—C32—C27 | 120.0 |
C14—C15—H15A | 109.5 | C31—C32—H32 | 120.0 |
C14—C15—H15B | 109.5 | C27—C32—H32 | 120.0 |
H15A—C15—H15B | 109.5 | ||
C13—Sn1—O1—C1 | −63.6 (3) | C16—C14—C17—C18 | −66.0 (4) |
C3—Sn1—O1—C1 | 60.3 (3) | C13—C14—C17—C18 | 51.9 (4) |
C23—Sn1—O1—C1 | 179.4 (3) | C15—C14—C17—C22 | −7.0 (4) |
Sn1—O1—C1—O2 | −1.6 (6) | C16—C14—C17—C22 | 112.4 (3) |
Sn1—O1—C1—C2 | −178.3 (3) | C13—C14—C17—C22 | −129.6 (3) |
O2—C1—C2—C2i | −171.2 (6) | C22—C17—C18—C19 | 0.0 |
O1—C1—C2—C2i | 5.6 (8) | C14—C17—C18—C19 | 178.4 (3) |
O1—Sn1—C3—C4 | 90.0 (3) | C17—C18—C19—C20 | 0.0 |
C13—Sn1—C3—C4 | −155.2 (3) | C18—C19—C20—C21 | 0.0 |
C23—Sn1—C3—C4 | −9.6 (3) | C19—C20—C21—C22 | 0.0 |
Sn1—C3—C4—C5 | −66.3 (4) | C20—C21—C22—C17 | 0.0 |
Sn1—C3—C4—C6 | 175.8 (3) | C18—C17—C22—C21 | 0.0 |
Sn1—C3—C4—C7 | 57.2 (4) | C14—C17—C22—C21 | −178.4 (3) |
C5—C4—C7—C8 | −30.0 (4) | O1—Sn1—C23—C24 | 90.3 (3) |
C6—C4—C7—C8 | 89.8 (3) | C13—Sn1—C23—C24 | −17.6 (4) |
C3—C4—C7—C8 | −151.4 (2) | C3—Sn1—C23—C24 | −164.1 (3) |
C5—C4—C7—C12 | 150.1 (3) | Sn1—C23—C24—C26 | −56.6 (4) |
C6—C4—C7—C12 | −90.0 (3) | Sn1—C23—C24—C27 | 68.5 (4) |
C3—C4—C7—C12 | 28.8 (4) | Sn1—C23—C24—C25 | −174.0 (3) |
C12—C7—C8—C9 | 0.0 | C26—C24—C27—C28 | 171.4 (3) |
C4—C7—C8—C9 | −179.8 (3) | C23—C24—C27—C28 | 49.3 (4) |
C7—C8—C9—C10 | 0.0 | C25—C24—C27—C28 | −69.3 (4) |
C8—C9—C10—C11 | 0.0 | C26—C24—C27—C32 | −10.2 (4) |
C9—C10—C11—C12 | 0.0 | C23—C24—C27—C32 | −132.4 (3) |
C10—C11—C12—C7 | 0.0 | C25—C24—C27—C32 | 109.1 (3) |
C8—C7—C12—C11 | 0.0 | C32—C27—C28—C29 | 0.0 |
C4—C7—C12—C11 | 179.8 (3) | C24—C27—C28—C29 | 178.4 (3) |
O1—Sn1—C13—C14 | 118.8 (3) | C27—C28—C29—C30 | 0.0 |
C3—Sn1—C13—C14 | 5.3 (4) | C28—C29—C30—C31 | 0.0 |
C23—Sn1—C13—C14 | −141.0 (3) | C29—C30—C31—C32 | 0.0 |
Sn1—C13—C14—C17 | 57.4 (4) | C30—C31—C32—C27 | 0.0 |
Sn1—C13—C14—C15 | −67.2 (4) | C28—C27—C32—C31 | 0.0 |
Sn1—C13—C14—C16 | 176.4 (3) | C24—C27—C32—C31 | −178.4 (3) |
C15—C14—C17—C18 | 174.6 (3) |
Symmetry code: (i) −x, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | [Sn2(C10H13)6(C4H2O4)] |
Mr | 1150.66 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 9.6017 (9), 18.6352 (18), 16.5097 (16) |
β (°) | 91.985 (1) |
V (Å3) | 2952.3 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.89 |
Crystal size (mm) | 0.22 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.828, 0.932 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23553, 6102, 4565 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.101, 1.03 |
No. of reflections | 6102 |
No. of parameters | 286 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.67, −0.40 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.
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The structural chemistry of organotin carboxylates continues to receive attention owing to their biological properties, especially their antitumour activities (Chandrasekhar et al., 2002; Gielen et al., 2005). Recently, we have reported several tris(2-methyl-2-phenylpropyl)tin carboxylates, such as bis[tris(2-methyl-2-phenylpropyl)tin(IV)] 3,4,5,6-tetrafluorophthalate (Tian et al., 2004), bis[tris(2-methyl-2-phenylpropyl)tin(IV)] phthalate (Tian, Sun, Yang & Ng, 2005), tris(2-methyl-2-phenylpropyl)tin pyridine-3-carboxylate (Tian, Sun, Yang & Yang, 2005) and tris(2-methyl-2-phenylpropyl)tin 2-phthalimidoacetate (Tian et al., 2006), which all possess a distorted tetrahedral geometry. In the title compound, (I), tetrahedral coordination is also observed (Fig. 1 & Table 1). The Sn···O2 separation of 3.072 (4)Å indicates there is a weak interaction between these atoms, which distorts the tetrahedral geometry. The three Sn—C distances are almost identical. The Sn—O bond length in (I) is similar to that found in the carboxylate structures mentioned above.