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The Sn atom in the title compound, [Sn(CH3)2(C15H9Cl2O2)2], has a highly distorted octahedral coordination that may be best described as skew-trapezoid planar for the carboxylates. The ligands are asymmetrically coordinated to the Sn atoms with Sn—O covalent bonds and dative bonds. The mean Sn—C distance for the methyl groups is 2.094 (6) Å, with a bent C—Sn—C angle of 145.77 (11)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014710/lh6234sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014710/lh6234Isup2.hkl
Contains datablock I

CCDC reference: 245149

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.032
  • wR factor = 0.075
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn1 - O4 .. 5.10 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Bis[2,3-bis(4-chlorophenyl)propenoato-κ2O,O']dimethyltin(IV) top
Crystal data top
[Sn(CH3)2(C15H9Cl2O2)2]Z = 2
Mr = 733.00F(000) = 732
Triclinic, P1Dx = 1.625 Mg m3
Hall symbol: -P 1Melting point: 473-476 K K
a = 8.4740 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2770 (12) ÅCell parameters from 12446 reflections
c = 19.472 (4) Åθ = 3.1–27.3°
α = 95.817 (6)°µ = 1.25 mm1
β = 99.748 (7)°T = 173 K
γ = 114.116 (8)°Prism, colorless
V = 1497.7 (4) Å30.14 × 0.12 × 0.10 mm
Data collection top
Nonius KappaCCD
diffractometer
6683 independent reflections
Radiation source: fine-focus sealed tube5570 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω and φ scansθmax = 27.3°, θmin = 3.1°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1010
Tmin = 0.845, Tmax = 0.886k = 1313
12446 measured reflectionsl = 2525
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0343P)2 + 0.4509P]
where P = (Fo2 + 2Fc2)/3
6683 reflections(Δ/σ)max = 0.01
372 parametersΔρmax = 0.43 e Å3
0 restraintsΔρmin = 0.68 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.26139 (2)0.005495 (17)0.417574 (9)0.02159 (7)
Cl10.24802 (11)0.55145 (9)0.01231 (4)0.0531 (2)
Cl20.71382 (10)0.12751 (9)0.03621 (4)0.0447 (2)
Cl30.02708 (9)0.65950 (7)0.62064 (4)0.03262 (16)
Cl41.05421 (10)0.80855 (8)0.90539 (4)0.04376 (19)
O10.0518 (2)0.02613 (19)0.35061 (9)0.0303 (4)
O20.0772 (2)0.16400 (18)0.29998 (9)0.0281 (4)
O30.2828 (2)0.19300 (18)0.48343 (9)0.0262 (4)
O40.4908 (2)0.13198 (18)0.53037 (9)0.0281 (4)
C10.1230 (3)0.1579 (3)0.46970 (15)0.0305 (6)
H1A0.20030.14990.51500.046*
H1B0.08600.25310.44010.046*
H1C0.01780.14760.47840.046*
C20.4616 (4)0.0795 (3)0.36113 (15)0.0339 (6)
H2A0.57460.14530.39410.051*
H2B0.43000.13120.32560.051*
H2C0.47370.00360.33740.051*
C30.0026 (3)0.0817 (3)0.29848 (13)0.0243 (5)
C40.1431 (3)0.1031 (3)0.23630 (13)0.0245 (5)
C50.2237 (3)0.0140 (3)0.24145 (13)0.0251 (5)
H50.18860.04650.28680.030*
C60.1736 (3)0.2153 (3)0.17416 (13)0.0239 (5)
C70.0449 (4)0.1902 (3)0.13481 (14)0.0316 (6)
H70.06050.10160.14760.038*
C80.0681 (4)0.2928 (3)0.07707 (15)0.0352 (6)
H80.01970.27420.05010.042*
C90.2200 (4)0.4219 (3)0.05950 (14)0.0319 (6)
C100.3494 (4)0.4506 (3)0.09780 (15)0.0325 (6)
H100.45330.54020.08520.039*
C110.3258 (3)0.3467 (3)0.15506 (14)0.0272 (6)
H110.41470.36570.18150.033*
C120.3553 (3)0.0060 (3)0.18972 (14)0.0264 (6)
C130.4555 (3)0.0855 (3)0.12429 (14)0.0298 (6)
H130.44740.17400.11190.036*
C140.5661 (4)0.0489 (3)0.07751 (15)0.0323 (6)
H140.63320.11160.03330.039*
C150.5780 (3)0.0799 (3)0.09582 (14)0.0305 (6)
C160.4836 (4)0.1716 (3)0.16014 (15)0.0331 (6)
H160.49370.25930.17240.040*
C170.3743 (4)0.1337 (3)0.20629 (14)0.0302 (6)
H170.30980.19640.25080.036*
C180.4145 (3)0.2129 (3)0.53461 (13)0.0228 (5)
C190.4681 (3)0.3310 (2)0.59681 (13)0.0218 (5)
C200.6116 (3)0.3532 (3)0.64726 (13)0.0245 (5)
H200.65840.28460.63980.029*
C210.3564 (3)0.4112 (2)0.60124 (13)0.0202 (5)
C220.3138 (3)0.4765 (2)0.54587 (13)0.0222 (5)
H220.35400.46830.50370.027*
C230.2135 (3)0.5529 (2)0.55209 (13)0.0223 (5)
H230.18700.59890.51480.027*
C240.1520 (3)0.5620 (2)0.61307 (14)0.0231 (5)
C250.1876 (3)0.4945 (3)0.66803 (14)0.0263 (6)
H250.14330.49970.70940.032*
C260.2894 (3)0.4193 (3)0.66109 (13)0.0241 (5)
H260.31400.37210.69820.029*
C270.7075 (3)0.4645 (3)0.71148 (13)0.0250 (5)
C280.8130 (4)0.4355 (3)0.76525 (14)0.0321 (6)
H280.81280.34250.76070.038*
C290.9181 (4)0.5401 (3)0.82526 (15)0.0359 (7)
H290.98890.51890.86160.043*
C300.9188 (3)0.6749 (3)0.83167 (14)0.0310 (6)
C310.8164 (4)0.7075 (3)0.77893 (15)0.0317 (6)
H310.81870.80120.78370.038*
C320.7115 (3)0.6032 (3)0.71965 (14)0.0279 (6)
H320.64080.62540.68370.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02230 (10)0.01842 (9)0.02110 (10)0.00858 (7)0.00058 (7)0.00027 (7)
Cl10.0521 (5)0.0577 (5)0.0428 (5)0.0328 (4)0.0090 (4)0.0255 (4)
Cl20.0458 (4)0.0523 (4)0.0395 (4)0.0335 (4)0.0083 (3)0.0011 (3)
Cl30.0314 (4)0.0343 (3)0.0356 (4)0.0202 (3)0.0061 (3)0.0025 (3)
Cl40.0360 (4)0.0483 (4)0.0279 (4)0.0082 (3)0.0025 (3)0.0134 (3)
O10.0349 (10)0.0286 (9)0.0233 (10)0.0173 (9)0.0067 (8)0.0060 (8)
O20.0296 (10)0.0250 (9)0.0269 (10)0.0137 (8)0.0016 (8)0.0007 (7)
O30.0265 (9)0.0241 (9)0.0237 (9)0.0123 (8)0.0036 (8)0.0037 (7)
O40.0281 (10)0.0256 (9)0.0290 (10)0.0145 (8)0.0001 (8)0.0038 (8)
C10.0222 (13)0.0295 (14)0.0345 (16)0.0074 (12)0.0017 (12)0.0083 (12)
C20.0310 (15)0.0336 (15)0.0305 (15)0.0072 (13)0.0085 (12)0.0054 (12)
C30.0257 (13)0.0222 (12)0.0200 (13)0.0079 (11)0.0011 (11)0.0010 (10)
C40.0264 (13)0.0234 (13)0.0194 (13)0.0090 (11)0.0007 (11)0.0021 (10)
C50.0267 (13)0.0275 (13)0.0188 (13)0.0114 (11)0.0017 (11)0.0024 (10)
C60.0268 (13)0.0239 (12)0.0187 (13)0.0122 (11)0.0015 (10)0.0006 (10)
C70.0284 (14)0.0312 (14)0.0296 (15)0.0105 (12)0.0019 (12)0.0001 (12)
C80.0358 (16)0.0426 (16)0.0286 (15)0.0205 (14)0.0060 (13)0.0009 (13)
C90.0357 (16)0.0340 (15)0.0255 (14)0.0220 (13)0.0056 (12)0.0060 (12)
C100.0353 (15)0.0226 (13)0.0322 (16)0.0124 (12)0.0072 (13)0.0003 (11)
C110.0279 (14)0.0264 (13)0.0228 (13)0.0106 (12)0.0009 (11)0.0020 (11)
C120.0260 (13)0.0285 (13)0.0233 (14)0.0121 (12)0.0031 (11)0.0023 (11)
C130.0300 (14)0.0291 (14)0.0278 (15)0.0155 (12)0.0026 (12)0.0012 (11)
C140.0312 (15)0.0337 (15)0.0272 (15)0.0156 (13)0.0046 (12)0.0028 (12)
C150.0263 (14)0.0391 (15)0.0279 (15)0.0183 (13)0.0010 (12)0.0058 (12)
C160.0367 (16)0.0345 (15)0.0327 (16)0.0224 (13)0.0049 (13)0.0007 (12)
C170.0331 (15)0.0326 (14)0.0235 (14)0.0160 (13)0.0021 (12)0.0011 (11)
C180.0218 (12)0.0192 (12)0.0226 (13)0.0056 (10)0.0030 (10)0.0017 (10)
C190.0215 (12)0.0180 (11)0.0238 (13)0.0081 (10)0.0028 (10)0.0023 (10)
C200.0265 (13)0.0215 (12)0.0258 (14)0.0127 (11)0.0026 (11)0.0015 (10)
C210.0189 (12)0.0155 (11)0.0196 (12)0.0040 (10)0.0000 (10)0.0023 (9)
C220.0215 (12)0.0214 (12)0.0196 (13)0.0060 (10)0.0053 (10)0.0006 (10)
C230.0224 (13)0.0194 (12)0.0226 (13)0.0082 (11)0.0020 (10)0.0016 (10)
C240.0178 (12)0.0194 (12)0.0288 (14)0.0071 (10)0.0048 (10)0.0037 (10)
C250.0252 (13)0.0253 (13)0.0233 (14)0.0072 (11)0.0058 (11)0.0012 (11)
C260.0242 (13)0.0230 (12)0.0206 (13)0.0080 (11)0.0006 (10)0.0022 (10)
C270.0232 (13)0.0279 (13)0.0219 (13)0.0124 (11)0.0004 (11)0.0013 (10)
C280.0369 (16)0.0316 (14)0.0290 (15)0.0195 (13)0.0011 (12)0.0022 (12)
C290.0352 (16)0.0438 (16)0.0257 (15)0.0207 (14)0.0058 (12)0.0001 (13)
C300.0237 (13)0.0367 (15)0.0239 (14)0.0092 (12)0.0014 (11)0.0069 (12)
C310.0280 (14)0.0274 (14)0.0326 (16)0.0091 (12)0.0014 (12)0.0027 (12)
C320.0253 (13)0.0267 (13)0.0283 (14)0.0115 (12)0.0013 (11)0.0016 (11)
Geometric parameters (Å, º) top
Sn1—C12.089 (3)C12—C171.399 (4)
Sn1—C22.100 (3)C12—C131.403 (4)
Sn1—O12.116 (2)C13—C141.385 (4)
Sn1—O32.127 (2)C13—H130.9500
Sn1—O42.491 (2)C14—C151.384 (4)
Sn1—O22.544 (2)C14—H140.9500
Cl1—C91.743 (3)C15—C161.379 (4)
Cl2—C151.742 (3)C16—C171.379 (4)
Cl3—C241.743 (2)C16—H160.9500
Cl4—C301.737 (3)C17—H170.9500
O1—C31.297 (3)C18—C191.487 (3)
O2—C31.246 (3)C19—C201.348 (3)
O3—C181.294 (3)C19—C211.495 (3)
O4—C181.249 (3)C20—C271.463 (3)
C1—H1A0.9800C20—H200.9500
C1—H1B0.9800C21—C261.389 (4)
C1—H1C0.9800C21—C221.398 (3)
C2—H2A0.9800C22—C231.384 (3)
C2—H2B0.9800C22—H220.9500
C2—H2C0.9800C23—C241.384 (4)
C3—C41.502 (3)C23—H230.9500
C4—C51.353 (3)C24—C251.389 (4)
C4—C61.493 (3)C25—C261.386 (3)
C5—C121.466 (3)C25—H250.9500
C5—H50.9500C26—H260.9500
C6—C71.392 (4)C27—C281.396 (4)
C6—C111.393 (4)C27—C321.404 (3)
C7—C81.389 (4)C28—C291.387 (4)
C7—H70.9500C28—H280.9500
C8—C91.378 (4)C29—C301.376 (4)
C8—H80.9500C29—H290.9500
C9—C101.379 (4)C30—C311.387 (4)
C10—C111.390 (4)C31—C321.377 (4)
C10—H100.9500C31—H310.9500
C11—H110.9500C32—H320.9500
C1—Sn1—C2145.77 (11)C14—C13—C12121.1 (2)
C1—Sn1—O1101.90 (9)C14—C13—H13119.5
C2—Sn1—O1100.97 (10)C12—C13—H13119.5
C1—Sn1—O3101.12 (9)C15—C14—C13119.4 (2)
C2—Sn1—O3106.20 (9)C15—C14—H14120.3
O1—Sn1—O384.27 (6)C13—C14—H14120.3
C1—Sn1—O489.28 (9)C16—C15—C14121.3 (2)
C2—Sn1—O489.19 (9)C16—C15—Cl2119.4 (2)
O1—Sn1—O4140.23 (6)C14—C15—Cl2119.3 (2)
O3—Sn1—O456.03 (6)C15—C16—C17118.8 (2)
C1—Sn1—O288.61 (9)C15—C16—H16120.6
C2—Sn1—O283.70 (9)C17—C16—H16120.6
O1—Sn1—O255.55 (6)C16—C17—C12122.1 (3)
O3—Sn1—O2139.83 (6)C16—C17—H17118.9
O4—Sn1—O2164.02 (5)C12—C17—H17118.9
C3—O1—Sn1101.33 (14)O4—C18—O3119.1 (2)
C3—O2—Sn182.90 (14)O4—C18—C19122.4 (2)
C18—O3—Sn1100.18 (14)O3—C18—C19118.5 (2)
C18—O4—Sn184.58 (14)C20—C19—C18116.7 (2)
Sn1—C1—H1A109.5C20—C19—C21124.6 (2)
Sn1—C1—H1B109.5C18—C19—C21118.7 (2)
H1A—C1—H1B109.5C19—C20—C27131.1 (2)
Sn1—C1—H1C109.5C19—C20—H20114.4
H1A—C1—H1C109.5C27—C20—H20114.4
H1B—C1—H1C109.5C26—C21—C22118.7 (2)
Sn1—C2—H2A109.5C26—C21—C19119.6 (2)
Sn1—C2—H2B109.5C22—C21—C19121.7 (2)
H2A—C2—H2B109.5C23—C22—C21120.5 (2)
Sn1—C2—H2C109.5C23—C22—H22119.8
H2A—C2—H2C109.5C21—C22—H22119.8
H2B—C2—H2C109.5C22—C23—C24119.5 (2)
O2—C3—O1120.2 (2)C22—C23—H23120.2
O2—C3—C4121.1 (2)C24—C23—H23120.2
O1—C3—C4118.7 (2)C23—C24—C25121.2 (2)
C5—C4—C6127.8 (2)C23—C24—Cl3119.19 (19)
C5—C4—C3116.8 (2)C25—C24—Cl3119.6 (2)
C6—C4—C3115.3 (2)C26—C25—C24118.4 (2)
C4—C5—C12131.6 (2)C26—C25—H25120.8
C4—C5—H5114.2C24—C25—H25120.8
C12—C5—H5114.2C25—C26—C21121.6 (2)
C7—C6—C11118.5 (2)C25—C26—H26119.2
C7—C6—C4119.5 (2)C21—C26—H26119.2
C11—C6—C4122.0 (2)C28—C27—C32118.0 (2)
C8—C7—C6121.0 (3)C28—C27—C20118.0 (2)
C8—C7—H7119.5C32—C27—C20123.7 (2)
C6—C7—H7119.5C29—C28—C27121.1 (2)
C9—C8—C7119.1 (3)C29—C28—H28119.4
C9—C8—H8120.5C27—C28—H28119.4
C7—C8—H8120.5C30—C29—C28119.4 (2)
C8—C9—C10121.3 (3)C30—C29—H29120.3
C8—C9—Cl1119.1 (2)C28—C29—H29120.3
C10—C9—Cl1119.6 (2)C29—C30—C31120.9 (2)
C9—C10—C11119.2 (3)C29—C30—Cl4119.9 (2)
C9—C10—H10120.4C31—C30—Cl4119.2 (2)
C11—C10—H10120.4C32—C31—C30119.6 (2)
C10—C11—C6120.9 (3)C32—C31—H31120.2
C10—C11—H11119.6C30—C31—H31120.2
C6—C11—H11119.6C31—C32—C27121.0 (2)
C17—C12—C13117.4 (2)C31—C32—H32119.5
C17—C12—C5115.9 (2)C27—C32—H32119.5
C13—C12—C5126.6 (2)
C1—Sn1—O1—C380.61 (17)C17—C12—C13—C141.3 (4)
C2—Sn1—O1—C373.75 (17)C5—C12—C13—C14175.0 (3)
O3—Sn1—O1—C3179.19 (16)C12—C13—C14—C150.2 (4)
O4—Sn1—O1—C3175.91 (14)C13—C14—C15—C160.8 (4)
O2—Sn1—O1—C30.68 (14)C13—C14—C15—Cl2178.7 (2)
C1—Sn1—O2—C3106.17 (16)C14—C15—C16—C170.7 (4)
C2—Sn1—O2—C3107.24 (17)Cl2—C15—C16—C17178.9 (2)
O1—Sn1—O2—C30.70 (15)C15—C16—C17—C120.5 (4)
O3—Sn1—O2—C30.49 (19)C13—C12—C17—C161.4 (4)
O4—Sn1—O2—C3171.3 (2)C5—C12—C17—C16175.2 (3)
C1—Sn1—O3—C1879.62 (16)Sn1—O4—C18—O33.0 (2)
C2—Sn1—O3—C1879.55 (17)Sn1—O4—C18—C19176.4 (2)
O1—Sn1—O3—C18179.34 (15)Sn1—O3—C18—O43.6 (3)
O4—Sn1—O3—C181.88 (14)Sn1—O3—C18—C19175.89 (18)
O2—Sn1—O3—C18179.18 (13)O4—C18—C19—C203.9 (4)
C1—Sn1—O4—C18102.03 (16)O3—C18—C19—C20176.7 (2)
C2—Sn1—O4—C18112.17 (16)O4—C18—C19—C21173.0 (2)
O1—Sn1—O4—C185.87 (19)O3—C18—C19—C216.4 (3)
O3—Sn1—O4—C181.92 (14)C18—C19—C20—C27174.8 (3)
O2—Sn1—O4—C18175.6 (2)C21—C19—C20—C278.5 (5)
Sn1—O2—C3—O11.1 (2)C20—C19—C21—C2651.7 (3)
Sn1—O2—C3—C4177.9 (2)C18—C19—C21—C26125.0 (3)
Sn1—O1—C3—O21.3 (3)C20—C19—C21—C22129.6 (3)
Sn1—O1—C3—C4177.67 (19)C18—C19—C21—C2253.7 (3)
O2—C3—C4—C5176.0 (2)C26—C21—C22—C232.8 (4)
O1—C3—C4—C55.1 (4)C19—C21—C22—C23178.5 (2)
O2—C3—C4—C67.6 (4)C21—C22—C23—C241.4 (4)
O1—C3—C4—C6171.3 (2)C22—C23—C24—C250.7 (4)
C6—C4—C5—C122.9 (5)C22—C23—C24—Cl3179.58 (19)
C3—C4—C5—C12173.0 (3)C23—C24—C25—C261.1 (4)
C5—C4—C6—C7107.7 (3)Cl3—C24—C25—C26179.11 (18)
C3—C4—C6—C768.3 (3)C24—C25—C26—C210.4 (4)
C5—C4—C6—C1173.9 (4)C22—C21—C26—C252.3 (4)
C3—C4—C6—C11110.2 (3)C19—C21—C26—C25178.9 (2)
C11—C6—C7—C80.9 (4)C19—C20—C27—C28159.5 (3)
C4—C6—C7—C8179.4 (2)C19—C20—C27—C3226.1 (5)
C6—C7—C8—C91.0 (4)C32—C27—C28—C290.4 (4)
C7—C8—C9—C100.4 (4)C20—C27—C28—C29175.1 (3)
C7—C8—C9—Cl1179.3 (2)C27—C28—C29—C300.3 (5)
C8—C9—C10—C110.3 (4)C28—C29—C30—C310.2 (5)
Cl1—C9—C10—C11179.89 (19)C28—C29—C30—Cl4178.3 (2)
C9—C10—C11—C60.3 (4)C29—C30—C31—C320.6 (4)
C7—C6—C11—C100.3 (4)Cl4—C30—C31—C32178.7 (2)
C4—C6—C11—C10178.7 (2)C30—C31—C32—C270.5 (4)
C4—C5—C12—C17163.1 (3)C28—C27—C32—C310.0 (4)
C4—C5—C12—C1313.2 (5)C20—C27—C32—C31174.4 (3)
 

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