

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809038872/sj2651sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809038872/sj2651Isup2.hkl |
CCDC reference: 750576
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.014 Å
- R factor = 0.047
- wR factor = 0.107
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 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 Sn2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang .. 14 PLAT041_ALERT_1_C Calc. and Reported SumFormula Strings Differ ? PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT234_ALERT_4_C Large Hirshfeld Difference Cl1 -- C4 .. 0.17 Ang.
Alert level G PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large. 9.05 PLAT128_ALERT_4_G Non-standard setting of Space-group P21/c .... P21/n PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4 O3 -SN1 -O1 -C1 -159.00 9.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 8 O4 -SN2 -O2 -C1 -167.00 2.00 4.666 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 12 O1 -SN1 -O3 -C9 -83.00 10.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The reaction was carried out under a nitrogen atmosphere. 2-(2-chlorophenyl)acetic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to a stirred solution of benzene (30 ml) in a Schlenk flask and stirred for 0.5 h. Trimethyltin chloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at room temperature. The resulting clear solution was evaporated under vacuum. The product was crystallized from a solution of dichloromethane/methanol (1:1) to yield colourless blocks of the title compound (yield 81%. m.p.390 K). Anal. Calcd (%) for C11H15Cl1O2Sn1 (Mr = 333.37): C,39.63; H, 4.54; Cl, 10.63. Found (%): C, 39.51; H, 4.64; Cl, 10.75.
The H atoms were positioned geometrically, with methyl C—H distances of 0.96 Å and aromatic C—H distances of 0.93 Å, and refined as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C, O) or 1.5 Ueq(C) for the methyl groups.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Sn(CH3)3(C8H6ClO2)] | F(000) = 1312 |
Mr = 333.39 | Dx = 1.620 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4326 reflections |
a = 7.0754 (9) Å | θ = 2.6–24.8° |
b = 28.306 (3) Å | µ = 2.05 mm−1 |
c = 13.6721 (15) Å | T = 298 K |
β = 93.117 (2)° | Block, colourless |
V = 2734.1 (5) Å3 | 0.49 × 0.32 × 0.15 mm |
Z = 8 |
Siemens SMART CCD area-detector diffractometer | 4820 independent reflections |
Radiation source: fine-focus sealed tube | 3411 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.434, Tmax = 0.749 | k = −33→33 |
14063 measured reflections | l = −10→16 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0224P)2 + 9.0463P] where P = (Fo2 + 2Fc2)/3 |
4820 reflections | (Δ/σ)max = 0.001 |
277 parameters | Δρmax = 1.09 e Å−3 |
0 restraints | Δρmin = −0.92 e Å−3 |
[Sn(CH3)3(C8H6ClO2)] | V = 2734.1 (5) Å3 |
Mr = 333.39 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.0754 (9) Å | µ = 2.05 mm−1 |
b = 28.306 (3) Å | T = 298 K |
c = 13.6721 (15) Å | 0.49 × 0.32 × 0.15 mm |
β = 93.117 (2)° |
Siemens SMART CCD area-detector diffractometer | 4820 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3411 reflections with I > 2σ(I) |
Tmin = 0.434, Tmax = 0.749 | Rint = 0.056 |
14063 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.05 | Δρmax = 1.09 e Å−3 |
4820 reflections | Δρmin = −0.92 e Å−3 |
277 parameters |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.02624 (7) | 0.138217 (16) | 0.88059 (3) | 0.04764 (16) | |
Sn2 | 0.20583 (7) | 0.212967 (17) | 1.21572 (3) | 0.04848 (16) | |
Cl1 | 0.4073 (6) | 0.03321 (16) | 1.1310 (3) | 0.1655 (15) | |
Cl2 | −0.2267 (4) | 0.14040 (10) | 0.36127 (15) | 0.0943 (8) | |
O1 | 0.1070 (7) | 0.14009 (16) | 1.0530 (3) | 0.0583 (13) | |
O2 | 0.1197 (7) | 0.13802 (16) | 1.2145 (3) | 0.0572 (13) | |
O3 | −0.0431 (7) | 0.13733 (16) | 0.7223 (3) | 0.0564 (13) | |
O4 | −0.1907 (7) | 0.20535 (18) | 0.7318 (3) | 0.0620 (14) | |
C1 | 0.0842 (11) | 0.1192 (3) | 1.1319 (5) | 0.0553 (19) | |
C2 | 0.0044 (13) | 0.0697 (3) | 1.1322 (6) | 0.073 (2) | |
H2A | −0.1323 | 0.0720 | 1.1333 | 0.088* | |
H2B | 0.0328 | 0.0546 | 1.0710 | 0.088* | |
C3 | 0.0721 (17) | 0.0382 (3) | 1.2138 (7) | 0.079 (3) | |
C4 | 0.2486 (19) | 0.0191 (4) | 1.2200 (8) | 0.103 (3) | |
C5 | 0.316 (2) | −0.0112 (4) | 1.2941 (10) | 0.127 (4) | |
H5 | 0.4382 | −0.0237 | 1.2975 | 0.153* | |
C6 | 0.184 (3) | −0.0208 (4) | 1.3620 (10) | 0.121 (5) | |
H6 | 0.2224 | −0.0410 | 1.4131 | 0.145* | |
C7 | 0.001 (2) | −0.0036 (4) | 1.3623 (9) | 0.115 (4) | |
H7 | −0.0816 | −0.0121 | 1.4100 | 0.138* | |
C8 | −0.0504 (18) | 0.0264 (3) | 1.2880 (8) | 0.100 (3) | |
H8 | −0.1708 | 0.0397 | 1.2861 | 0.120* | |
C9 | −0.1339 (10) | 0.1720 (3) | 0.6832 (5) | 0.0504 (18) | |
C10 | −0.1744 (10) | 0.1690 (3) | 0.5734 (5) | 0.0553 (19) | |
H10A | −0.0690 | 0.1534 | 0.5443 | 0.066* | |
H10B | −0.1837 | 0.2007 | 0.5469 | 0.066* | |
C11 | −0.3557 (10) | 0.1423 (2) | 0.5447 (5) | 0.0514 (18) | |
C12 | −0.3923 (11) | 0.1278 (3) | 0.4478 (6) | 0.062 (2) | |
C13 | −0.5520 (14) | 0.1049 (3) | 0.4182 (7) | 0.079 (3) | |
H13 | −0.5713 | 0.0958 | 0.3531 | 0.095* | |
C14 | −0.6863 (13) | 0.0950 (3) | 0.4838 (7) | 0.080 (3) | |
H14 | −0.7967 | 0.0792 | 0.4633 | 0.097* | |
C15 | −0.6576 (12) | 0.1084 (3) | 0.5797 (7) | 0.072 (2) | |
H15 | −0.7488 | 0.1020 | 0.6244 | 0.086* | |
C16 | −0.4919 (11) | 0.1317 (3) | 0.6100 (6) | 0.064 (2) | |
H16 | −0.4723 | 0.1403 | 0.6754 | 0.077* | |
C17 | 0.1855 (13) | 0.0758 (3) | 0.8683 (6) | 0.079 (3) | |
H17A | 0.2891 | 0.0759 | 0.9167 | 0.119* | |
H17B | 0.2338 | 0.0741 | 0.8041 | 0.119* | |
H17C | 0.1062 | 0.0489 | 0.8785 | 0.119* | |
C18 | −0.2588 (11) | 0.1335 (3) | 0.9193 (6) | 0.077 (2) | |
H18A | −0.3086 | 0.1030 | 0.9012 | 0.115* | |
H18B | −0.3322 | 0.1576 | 0.8855 | 0.115* | |
H18C | −0.2649 | 0.1378 | 0.9887 | 0.115* | |
C19 | 0.1885 (11) | 0.2012 (3) | 0.8801 (5) | 0.069 (2) | |
H19A | 0.3035 | 0.1969 | 0.9196 | 0.103* | |
H19B | 0.1171 | 0.2266 | 0.9062 | 0.103* | |
H19C | 0.2183 | 0.2086 | 0.8141 | 0.103* | |
C20 | −0.0375 (10) | 0.2385 (3) | 1.1363 (6) | 0.067 (2) | |
H20A | −0.0001 | 0.2560 | 1.0803 | 0.100* | |
H20B | −0.1072 | 0.2588 | 1.1776 | 0.100* | |
H20C | −0.1158 | 0.2124 | 1.1149 | 0.100* | |
C21 | 0.2034 (13) | 0.2164 (3) | 1.3703 (5) | 0.075 (3) | |
H21A | 0.1478 | 0.2458 | 1.3891 | 0.112* | |
H21B | 0.3308 | 0.2145 | 1.3980 | 0.112* | |
H21C | 0.1306 | 0.1906 | 1.3939 | 0.112* | |
C22 | 0.4641 (10) | 0.2008 (3) | 1.1510 (6) | 0.071 (2) | |
H22A | 0.4750 | 0.1678 | 1.1356 | 0.107* | |
H22B | 0.5669 | 0.2099 | 1.1957 | 0.107* | |
H22C | 0.4684 | 0.2191 | 1.0920 | 0.107* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0547 (3) | 0.0418 (3) | 0.0458 (3) | 0.0031 (2) | −0.0036 (2) | −0.0021 (2) |
Sn2 | 0.0490 (3) | 0.0512 (3) | 0.0451 (3) | −0.0101 (2) | 0.0020 (2) | −0.0036 (2) |
Cl1 | 0.138 (3) | 0.195 (4) | 0.163 (3) | 0.045 (3) | 0.005 (3) | 0.002 (3) |
Cl2 | 0.1043 (18) | 0.130 (2) | 0.0492 (12) | −0.0172 (16) | 0.0086 (12) | −0.0131 (13) |
O1 | 0.083 (4) | 0.046 (3) | 0.045 (3) | −0.007 (3) | −0.002 (2) | 0.000 (2) |
O2 | 0.083 (4) | 0.047 (3) | 0.041 (3) | −0.015 (3) | −0.001 (2) | −0.003 (2) |
O3 | 0.074 (3) | 0.049 (3) | 0.045 (3) | 0.017 (3) | −0.008 (2) | −0.007 (2) |
O4 | 0.073 (4) | 0.058 (3) | 0.054 (3) | 0.022 (3) | −0.009 (3) | −0.005 (3) |
C1 | 0.071 (5) | 0.046 (4) | 0.048 (4) | −0.003 (4) | −0.007 (4) | 0.001 (4) |
C2 | 0.102 (7) | 0.057 (5) | 0.059 (5) | −0.019 (5) | −0.013 (5) | 0.001 (4) |
C3 | 0.122 (9) | 0.044 (5) | 0.068 (6) | −0.019 (5) | −0.016 (6) | −0.006 (4) |
C4 | 0.145 (11) | 0.071 (7) | 0.088 (7) | −0.001 (7) | −0.021 (8) | −0.002 (6) |
C5 | 0.181 (14) | 0.084 (9) | 0.113 (10) | 0.012 (9) | −0.035 (10) | −0.006 (8) |
C6 | 0.195 (16) | 0.064 (8) | 0.101 (10) | −0.014 (9) | −0.027 (10) | 0.006 (7) |
C7 | 0.178 (14) | 0.078 (8) | 0.089 (8) | −0.040 (9) | −0.007 (9) | −0.002 (7) |
C8 | 0.153 (10) | 0.060 (6) | 0.084 (7) | −0.026 (6) | −0.011 (7) | −0.003 (6) |
C9 | 0.051 (4) | 0.057 (5) | 0.043 (4) | 0.007 (4) | −0.002 (3) | 0.001 (4) |
C10 | 0.055 (5) | 0.063 (5) | 0.047 (4) | 0.003 (4) | −0.006 (3) | −0.001 (4) |
C11 | 0.050 (4) | 0.053 (5) | 0.051 (4) | 0.007 (3) | −0.007 (3) | 0.000 (3) |
C12 | 0.064 (5) | 0.061 (5) | 0.060 (5) | 0.002 (4) | −0.009 (4) | −0.010 (4) |
C13 | 0.087 (7) | 0.074 (6) | 0.074 (6) | −0.010 (5) | −0.012 (5) | −0.010 (5) |
C14 | 0.077 (6) | 0.068 (6) | 0.094 (7) | −0.012 (5) | −0.012 (5) | −0.002 (5) |
C15 | 0.063 (5) | 0.070 (6) | 0.083 (6) | −0.010 (4) | 0.008 (5) | 0.005 (5) |
C16 | 0.068 (5) | 0.066 (5) | 0.058 (5) | 0.000 (4) | 0.000 (4) | 0.000 (4) |
C17 | 0.106 (7) | 0.071 (6) | 0.060 (5) | 0.036 (5) | −0.013 (5) | −0.009 (4) |
C18 | 0.059 (5) | 0.093 (7) | 0.078 (6) | −0.008 (5) | 0.006 (4) | 0.006 (5) |
C19 | 0.074 (5) | 0.075 (6) | 0.057 (5) | −0.017 (4) | 0.000 (4) | 0.012 (4) |
C20 | 0.050 (5) | 0.063 (5) | 0.086 (6) | 0.003 (4) | 0.001 (4) | −0.010 (4) |
C21 | 0.117 (7) | 0.068 (6) | 0.039 (4) | −0.029 (5) | 0.005 (4) | −0.004 (4) |
C22 | 0.057 (5) | 0.082 (6) | 0.076 (5) | −0.006 (4) | 0.006 (4) | −0.003 (5) |
Sn1—C17 | 2.107 (7) | C10—C11 | 1.522 (9) |
Sn1—C18 | 2.117 (7) | C10—H10A | 0.9700 |
Sn1—C19 | 2.120 (7) | C10—H10B | 0.9700 |
Sn1—O3 | 2.194 (4) | C11—C16 | 1.381 (10) |
Sn1—O1 | 2.396 (5) | C11—C12 | 1.397 (10) |
Sn2—C22 | 2.102 (7) | C12—C13 | 1.345 (11) |
Sn2—C20 | 2.113 (7) | C13—C14 | 1.371 (12) |
Sn2—C21 | 2.117 (7) | C13—H13 | 0.9300 |
Sn2—O2 | 2.207 (5) | C14—C15 | 1.369 (11) |
Sn2—O4i | 2.432 (5) | C14—H14 | 0.9300 |
Cl1—C4 | 1.746 (12) | C15—C16 | 1.389 (11) |
Cl2—C12 | 1.747 (8) | C15—H15 | 0.9300 |
O1—C1 | 1.249 (8) | C16—H16 | 0.9300 |
O2—C1 | 1.263 (8) | C17—H17A | 0.9600 |
O3—C9 | 1.273 (8) | C17—H17B | 0.9600 |
O4—C9 | 1.235 (8) | C17—H17C | 0.9600 |
O4—Sn2ii | 2.432 (5) | C18—H18A | 0.9600 |
C1—C2 | 1.510 (10) | C18—H18B | 0.9600 |
C2—C3 | 1.487 (11) | C18—H18C | 0.9600 |
C2—H2A | 0.9700 | C19—H19A | 0.9600 |
C2—H2B | 0.9700 | C19—H19B | 0.9600 |
C3—C4 | 1.359 (14) | C19—H19C | 0.9600 |
C3—C8 | 1.411 (13) | C20—H20A | 0.9600 |
C4—C5 | 1.395 (15) | C20—H20B | 0.9600 |
C5—C6 | 1.380 (17) | C20—H20C | 0.9600 |
C5—H5 | 0.9300 | C21—H21A | 0.9600 |
C6—C7 | 1.387 (17) | C21—H21B | 0.9600 |
C6—H6 | 0.9300 | C21—H21C | 0.9600 |
C7—C8 | 1.358 (14) | C22—H22A | 0.9600 |
C7—H7 | 0.9300 | C22—H22B | 0.9600 |
C8—H8 | 0.9300 | C22—H22C | 0.9600 |
C9—C10 | 1.515 (9) | ||
C17—Sn1—C18 | 119.2 (4) | C9—C10—H10B | 108.9 |
C17—Sn1—C19 | 114.4 (4) | C11—C10—H10B | 108.9 |
C18—Sn1—C19 | 125.2 (3) | H10A—C10—H10B | 107.7 |
C17—Sn1—O3 | 90.2 (2) | C16—C11—C12 | 116.7 (7) |
C18—Sn1—O3 | 94.6 (3) | C16—C11—C10 | 123.3 (6) |
C19—Sn1—O3 | 95.6 (2) | C12—C11—C10 | 120.0 (7) |
C17—Sn1—O1 | 89.8 (2) | C13—C12—C11 | 122.4 (8) |
C18—Sn1—O1 | 86.3 (3) | C13—C12—Cl2 | 118.5 (7) |
C19—Sn1—O1 | 83.4 (2) | C11—C12—Cl2 | 119.1 (6) |
O3—Sn1—O1 | 178.93 (18) | C12—C13—C14 | 120.1 (8) |
C22—Sn2—C20 | 122.9 (3) | C12—C13—H13 | 119.9 |
C22—Sn2—C21 | 118.9 (3) | C14—C13—H13 | 119.9 |
C20—Sn2—C21 | 116.5 (3) | C15—C14—C13 | 119.9 (8) |
C22—Sn2—O2 | 94.9 (3) | C15—C14—H14 | 120.1 |
C20—Sn2—O2 | 96.2 (3) | C13—C14—H14 | 120.1 |
C21—Sn2—O2 | 92.0 (2) | C14—C15—C16 | 119.7 (8) |
C22—Sn2—O4i | 86.0 (3) | C14—C15—H15 | 120.1 |
C20—Sn2—O4i | 87.3 (2) | C16—C15—H15 | 120.1 |
C21—Sn2—O4i | 83.4 (2) | C11—C16—C15 | 121.2 (7) |
O2—Sn2—O4i | 175.08 (16) | C11—C16—H16 | 119.4 |
C1—O1—Sn1 | 143.5 (5) | C15—C16—H16 | 119.4 |
C1—O2—Sn2 | 117.0 (4) | Sn1—C17—H17A | 109.5 |
C9—O3—Sn1 | 119.0 (4) | Sn1—C17—H17B | 109.5 |
C9—O4—Sn2ii | 141.7 (5) | H17A—C17—H17B | 109.5 |
O1—C1—O2 | 122.9 (7) | Sn1—C17—H17C | 109.5 |
O1—C1—C2 | 120.6 (6) | H17A—C17—H17C | 109.5 |
O2—C1—C2 | 116.5 (6) | H17B—C17—H17C | 109.5 |
C3—C2—C1 | 116.9 (7) | Sn1—C18—H18A | 109.5 |
C3—C2—H2A | 108.1 | Sn1—C18—H18B | 109.5 |
C1—C2—H2A | 108.1 | H18A—C18—H18B | 109.5 |
C3—C2—H2B | 108.1 | Sn1—C18—H18C | 109.5 |
C1—C2—H2B | 108.1 | H18A—C18—H18C | 109.5 |
H2A—C2—H2B | 107.3 | H18B—C18—H18C | 109.5 |
C4—C3—C8 | 117.4 (10) | Sn1—C19—H19A | 109.5 |
C4—C3—C2 | 122.9 (10) | Sn1—C19—H19B | 109.5 |
C8—C3—C2 | 119.8 (10) | H19A—C19—H19B | 109.5 |
C3—C4—C5 | 124.7 (13) | Sn1—C19—H19C | 109.5 |
C3—C4—Cl1 | 119.3 (9) | H19A—C19—H19C | 109.5 |
C5—C4—Cl1 | 116.0 (12) | H19B—C19—H19C | 109.5 |
C6—C5—C4 | 113.0 (14) | Sn2—C20—H20A | 109.5 |
C6—C5—H5 | 123.5 | Sn2—C20—H20B | 109.5 |
C4—C5—H5 | 123.5 | H20A—C20—H20B | 109.5 |
C5—C6—C7 | 127.0 (13) | Sn2—C20—H20C | 109.5 |
C5—C6—H6 | 116.5 | H20A—C20—H20C | 109.5 |
C7—C6—H6 | 116.5 | H20B—C20—H20C | 109.5 |
C8—C7—C6 | 115.4 (13) | Sn2—C21—H21A | 109.5 |
C8—C7—H7 | 122.3 | Sn2—C21—H21B | 109.5 |
C6—C7—H7 | 122.3 | H21A—C21—H21B | 109.5 |
C7—C8—C3 | 122.5 (12) | Sn2—C21—H21C | 109.5 |
C7—C8—H8 | 118.8 | H21A—C21—H21C | 109.5 |
C3—C8—H8 | 118.8 | H21B—C21—H21C | 109.5 |
O4—C9—O3 | 122.4 (6) | Sn2—C22—H22A | 109.5 |
O4—C9—C10 | 121.7 (6) | Sn2—C22—H22B | 109.5 |
O3—C9—C10 | 115.9 (6) | H22A—C22—H22B | 109.5 |
C9—C10—C11 | 113.2 (6) | Sn2—C22—H22C | 109.5 |
C9—C10—H10A | 108.9 | H22A—C22—H22C | 109.5 |
C11—C10—H10A | 108.9 | H22B—C22—H22C | 109.5 |
C17—Sn1—O1—C1 | −67.1 (9) | Cl1—C4—C5—C6 | 179.9 (9) |
C18—Sn1—O1—C1 | 52.3 (9) | C4—C5—C6—C7 | −0.1 (19) |
C19—Sn1—O1—C1 | 178.4 (9) | C5—C6—C7—C8 | −1.2 (19) |
O3—Sn1—O1—C1 | −159 (9) | C6—C7—C8—C3 | 2.0 (15) |
C22—Sn2—O2—C1 | −66.8 (6) | C4—C3—C8—C7 | −1.6 (14) |
C20—Sn2—O2—C1 | 57.1 (6) | C2—C3—C8—C7 | 177.3 (8) |
C21—Sn2—O2—C1 | 174.0 (6) | Sn2ii—O4—C9—O3 | 160.1 (5) |
O4i—Sn2—O2—C1 | −167 (2) | Sn2ii—O4—C9—C10 | −22.1 (12) |
C17—Sn1—O3—C9 | −174.5 (6) | Sn1—O3—C9—O4 | −2.7 (9) |
C18—Sn1—O3—C9 | 66.2 (6) | Sn1—O3—C9—C10 | 179.3 (4) |
C19—Sn1—O3—C9 | −60.0 (6) | O4—C9—C10—C11 | −91.2 (9) |
O1—Sn1—O3—C9 | −83 (10) | O3—C9—C10—C11 | 86.7 (8) |
Sn1—O1—C1—O2 | −163.3 (5) | C9—C10—C11—C16 | 14.6 (10) |
Sn1—O1—C1—C2 | 14.4 (13) | C9—C10—C11—C12 | −166.5 (7) |
Sn2—O2—C1—O1 | 4.5 (10) | C16—C11—C12—C13 | 0.3 (11) |
Sn2—O2—C1—C2 | −173.3 (5) | C10—C11—C12—C13 | −178.7 (8) |
O1—C1—C2—C3 | 148.0 (8) | C16—C11—C12—Cl2 | 179.6 (6) |
O2—C1—C2—C3 | −34.2 (11) | C10—C11—C12—Cl2 | 0.6 (10) |
C1—C2—C3—C4 | −72.9 (11) | C11—C12—C13—C14 | 0.1 (13) |
C1—C2—C3—C8 | 108.2 (9) | Cl2—C12—C13—C14 | −179.1 (7) |
C8—C3—C4—C5 | 0.2 (15) | C12—C13—C14—C15 | −0.1 (14) |
C2—C3—C4—C5 | −178.7 (9) | C13—C14—C15—C16 | −0.4 (13) |
C8—C3—C4—Cl1 | −179.1 (7) | C12—C11—C16—C15 | −0.8 (11) |
C2—C3—C4—Cl1 | 2.0 (13) | C10—C11—C16—C15 | 178.1 (7) |
C3—C4—C5—C6 | 0.6 (17) | C14—C15—C16—C11 | 0.9 (12) |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Sn(CH3)3(C8H6ClO2)] |
Mr | 333.39 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 7.0754 (9), 28.306 (3), 13.6721 (15) |
β (°) | 93.117 (2) |
V (Å3) | 2734.1 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 2.05 |
Crystal size (mm) | 0.49 × 0.32 × 0.15 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.434, 0.749 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14063, 4820, 3411 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.107, 1.05 |
No. of reflections | 4820 |
No. of parameters | 277 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.09, −0.92 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Sn1—C17 | 2.107 (7) | Sn2—C22 | 2.102 (7) |
Sn1—C18 | 2.117 (7) | Sn2—C20 | 2.113 (7) |
Sn1—C19 | 2.120 (7) | Sn2—C21 | 2.117 (7) |
Sn1—O3 | 2.194 (4) | Sn2—O2 | 2.207 (5) |
Sn1—O1 | 2.396 (5) | Sn2—O4i | 2.432 (5) |
Symmetry code: (i) x+1/2, −y+1/2, z+1/2. |
The chemistry of organotin(IV) derivatives is a subject of study with growing interest due to their significant antimicrobial properties as well as antitumor activities (Wang et al., 2007). As a part of our ongoing investigations in this field we have synthesized the title compound and present its crystal structure here. The title compound, which is shown in Fig.1 forms an extended one-dimensional chain structure arising from Sn—O bridges formed by the 2-(2-chlorophenyl)acetato ligands. The Sn—O bond distances in the compound (Sn(1)—O(1) = 2.396 (5) Å; Sn(1)—O(3) = 2.194 (4) Å) are comparable to those found in related organotin carboxylates (Ma et al., 2006). The Sn atom assumes a slightly distorted trigonal-bipyramidal coordination geometry, provided by and three methyl groups in the equatorial positions and two O atoms of symmetry related carboxylate groups in the axial positions.