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The structure of the title compound, [Sn(C6H5)3(C14H9O3)], consists of monomeric species featuring a distorted tetra­hedral environment around the Sn centre. The tetra­hedral angles are non-equivalent, owing to the relatively close approach of a carboxyl­ate O atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051853/hk2167sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051853/hk2167Isup2.hkl
Contains datablock I

CCDC reference: 633884

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.034
  • wR factor = 0.095
  • Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sn - O3 .. 8.09 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: MAR software; cell refinement: marHKL (Klein & Bartels, 2000); data reduction: marHKL; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97.

(2-Benzoylbenzoato)triphenyltin(IV) top
Crystal data top
[Sn(C6H5)3(C14H9O3)]F(000) = 1160
Mr = 575.20Dx = 1.503 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 5835 reflections
a = 8.761 (3) Åθ = 3.0–27.5°
b = 17.363 (5) ŵ = 1.04 mm1
c = 17.752 (5) ÅT = 294 K
β = 109.73 (2)°Parallelipiped, colourless
V = 2541.9 (13) Å30.32 × 0.30 × 0.26 mm
Z = 4
Data collection top
Marresearch MAR345 image-plate
diffractometer
5667 reflections with I > 2σ(I)
Radiation source: RU200 rotating anodeRint = 0.039
Graphite monochromatorθmax = 27.5°, θmin = 2.6°
Detector resolution: 6.66 pixels mm-1h = 011
188 images, ΔΦ 3° scansk = 220
64928 measured reflectionsl = 2320
5835 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0462P)2 + 3.3458P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.002
5835 reflectionsΔρmax = 0.87 e Å3
326 parametersΔρmin = 0.77 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0275 (11)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn0.521950 (18)0.289494 (9)0.302662 (9)0.02543 (9)
O10.4959 (2)0.33041 (10)0.40830 (10)0.0276 (3)
C20.4036 (3)0.39189 (14)0.38780 (15)0.0268 (5)
O30.3639 (2)0.41772 (11)0.31894 (11)0.0322 (4)
C40.3463 (3)0.42648 (14)0.44979 (15)0.0278 (5)
C50.2682 (3)0.49800 (15)0.43343 (17)0.0324 (5)
H50.25520.52240.38500.039*
C60.2099 (4)0.53290 (16)0.48870 (19)0.0388 (6)
H60.15680.58010.47700.047*
C70.2312 (4)0.49717 (17)0.56143 (18)0.0382 (6)
H70.19220.52040.59850.046*
C80.3103 (3)0.42722 (17)0.57891 (17)0.0353 (6)
H80.32540.40400.62810.042*
C90.3679 (3)0.39105 (15)0.52368 (15)0.0288 (5)
C100.4511 (3)0.31435 (16)0.54900 (15)0.0305 (5)
O110.5812 (3)0.31272 (13)0.60317 (13)0.0413 (5)
C120.3649 (3)0.24229 (15)0.51326 (15)0.0292 (5)
C130.4443 (3)0.17252 (16)0.53861 (18)0.0345 (6)
H130.54880.17200.57570.041*
C140.3669 (4)0.10377 (17)0.5083 (2)0.0402 (6)
H140.42040.05720.52420.048*
C150.2097 (4)0.10474 (17)0.45437 (19)0.0404 (6)
H150.15770.05850.43480.048*
C160.1292 (4)0.17380 (17)0.42940 (18)0.0372 (6)
H160.02380.17400.39320.045*
C170.2075 (3)0.24300 (16)0.45895 (16)0.0326 (5)
H170.15440.28960.44230.039*
C180.6482 (3)0.18513 (14)0.34921 (15)0.0268 (5)
C190.6748 (3)0.13239 (15)0.29527 (16)0.0317 (5)
H190.64350.14500.24130.038*
C200.7473 (3)0.06134 (16)0.32108 (17)0.0339 (5)
H200.76500.02700.28470.041*
C210.7927 (3)0.04222 (16)0.40145 (18)0.0358 (6)
H210.84120.00510.41910.043*
C220.7661 (4)0.09331 (16)0.45524 (17)0.0359 (6)
H220.79590.08000.50900.043*
C230.6947 (3)0.16494 (15)0.42956 (16)0.0311 (5)
H230.67830.19920.46640.037*
C240.2848 (3)0.25974 (16)0.22675 (15)0.0288 (5)
C250.2092 (4)0.19690 (19)0.2474 (2)0.0430 (7)
H250.26480.16760.29220.052*
C260.0508 (4)0.1774 (2)0.2016 (3)0.0574 (9)
H260.00020.13580.21640.069*
C270.0307 (4)0.2197 (2)0.1346 (2)0.0529 (9)
H270.13610.20650.10380.064*
C280.0439 (4)0.2816 (2)0.1133 (2)0.0503 (9)
H280.01110.30980.06770.060*
C290.2014 (4)0.30241 (19)0.15967 (18)0.0389 (6)
H290.25030.34490.14550.047*
C300.6713 (3)0.36543 (14)0.26500 (15)0.0270 (5)
C310.6128 (3)0.43465 (16)0.22592 (17)0.0339 (5)
H310.50530.44870.21580.041*
C320.7150 (4)0.48269 (18)0.2021 (2)0.0439 (7)
H320.67530.52830.17520.053*
C330.8759 (4)0.4626 (2)0.2183 (2)0.0503 (8)
H330.94450.49530.20320.060*
C340.9352 (4)0.3940 (2)0.2568 (2)0.0468 (7)
H341.04320.38070.26750.056*
C350.8325 (3)0.34525 (17)0.27951 (17)0.0352 (6)
H350.87190.29880.30460.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn0.02292 (12)0.02561 (12)0.02716 (12)0.00058 (5)0.00769 (7)0.00154 (5)
O10.0289 (8)0.0257 (8)0.0289 (8)0.0020 (6)0.0107 (7)0.0002 (7)
C20.0235 (10)0.0261 (11)0.0304 (12)0.0029 (9)0.0087 (9)0.0005 (9)
O30.0331 (9)0.0324 (9)0.0323 (9)0.0015 (7)0.0127 (7)0.0042 (7)
C40.0235 (11)0.0273 (11)0.0314 (12)0.0014 (9)0.0077 (9)0.0009 (9)
C50.0312 (12)0.0280 (12)0.0374 (13)0.0007 (10)0.0108 (10)0.0009 (10)
C60.0362 (14)0.0298 (13)0.0487 (16)0.0042 (11)0.0120 (12)0.0061 (12)
C70.0360 (14)0.0397 (15)0.0408 (14)0.0005 (11)0.0154 (12)0.0123 (12)
C80.0337 (13)0.0401 (14)0.0315 (13)0.0008 (11)0.0102 (10)0.0042 (11)
C90.0259 (11)0.0290 (12)0.0312 (12)0.0030 (9)0.0093 (9)0.0026 (9)
C100.0292 (12)0.0351 (13)0.0274 (12)0.0004 (10)0.0100 (10)0.0007 (10)
O110.0332 (10)0.0446 (11)0.0382 (11)0.0060 (9)0.0016 (8)0.0017 (9)
C120.0310 (12)0.0282 (12)0.0308 (12)0.0000 (10)0.0136 (10)0.0041 (10)
C130.0335 (13)0.0319 (13)0.0404 (14)0.0031 (10)0.0155 (11)0.0101 (11)
C140.0430 (15)0.0288 (13)0.0559 (18)0.0032 (11)0.0261 (14)0.0080 (12)
C150.0481 (16)0.0304 (13)0.0481 (16)0.0067 (12)0.0233 (13)0.0003 (12)
C160.0373 (14)0.0346 (14)0.0388 (14)0.0059 (11)0.0115 (11)0.0008 (11)
C170.0336 (13)0.0283 (12)0.0351 (13)0.0012 (10)0.0103 (10)0.0039 (10)
C180.0236 (11)0.0246 (11)0.0306 (12)0.0017 (9)0.0069 (9)0.0033 (9)
C190.0289 (12)0.0329 (13)0.0310 (12)0.0001 (10)0.0073 (10)0.0031 (10)
C200.0294 (12)0.0303 (12)0.0419 (14)0.0029 (10)0.0120 (11)0.0092 (11)
C210.0328 (13)0.0260 (12)0.0480 (15)0.0013 (10)0.0127 (11)0.0019 (11)
C220.0410 (14)0.0312 (13)0.0346 (13)0.0021 (11)0.0114 (11)0.0079 (10)
C230.0350 (13)0.0288 (12)0.0311 (12)0.0004 (10)0.0132 (10)0.0009 (10)
C240.0219 (11)0.0350 (13)0.0282 (11)0.0018 (9)0.0069 (9)0.0038 (10)
C250.0387 (16)0.0414 (15)0.0465 (17)0.0099 (12)0.0112 (13)0.0020 (13)
C260.0436 (18)0.056 (2)0.072 (2)0.0218 (16)0.0193 (17)0.0129 (18)
C270.0283 (14)0.070 (2)0.055 (2)0.0058 (14)0.0076 (14)0.0241 (17)
C280.0318 (15)0.079 (3)0.0323 (15)0.0074 (14)0.0006 (12)0.0037 (14)
C290.0303 (13)0.0518 (16)0.0342 (14)0.0013 (12)0.0104 (11)0.0048 (12)
C300.0263 (11)0.0275 (11)0.0293 (11)0.0042 (9)0.0123 (9)0.0023 (9)
C310.0336 (13)0.0315 (13)0.0391 (14)0.0002 (10)0.0153 (11)0.0033 (11)
C320.0493 (17)0.0383 (15)0.0478 (17)0.0089 (13)0.0211 (14)0.0046 (13)
C330.0461 (17)0.058 (2)0.0533 (19)0.0207 (15)0.0255 (15)0.0015 (15)
C340.0270 (13)0.069 (2)0.0480 (17)0.0058 (13)0.0174 (12)0.0030 (15)
C350.0271 (12)0.0419 (14)0.0375 (14)0.0015 (11)0.0120 (10)0.0016 (11)
Geometric parameters (Å, º) top
Sn—O12.0885 (18)C18—C191.400 (4)
Sn—C302.118 (2)C19—C201.392 (4)
Sn—C242.123 (2)C19—H190.9300
Sn—C182.138 (2)C20—C211.386 (4)
O1—C21.314 (3)C20—H200.9300
C2—O31.237 (3)C21—C221.379 (4)
C2—C41.482 (3)C21—H210.9300
C4—C51.400 (4)C22—C231.398 (4)
C4—C91.403 (4)C22—H220.9300
C5—C61.389 (4)C23—H230.9300
C5—H50.9300C24—C291.383 (4)
C6—C71.387 (4)C24—C251.388 (4)
C6—H60.9300C25—C261.393 (5)
C7—C81.381 (4)C25—H250.9300
C7—H70.9300C26—C271.375 (6)
C8—C91.394 (4)C26—H260.9300
C8—H80.9300C27—C281.375 (6)
C9—C101.512 (4)C27—H270.9300
C10—O111.219 (3)C28—C291.395 (4)
C10—C121.488 (4)C28—H280.9300
C12—C171.390 (4)C29—H290.9300
C12—C131.394 (4)C30—C351.392 (4)
C13—C141.388 (4)C30—C311.396 (4)
C13—H130.9300C31—C321.390 (4)
C14—C151.387 (5)C31—H310.9300
C14—H140.9300C32—C331.385 (5)
C15—C161.386 (4)C32—H320.9300
C15—H150.9300C33—C341.383 (5)
C16—C171.395 (4)C33—H330.9300
C16—H160.9300C34—C351.391 (4)
C17—H170.9300C34—H340.9300
C18—C231.390 (4)C35—H350.9300
O1—Sn—C30109.75 (8)C20—C19—C18121.1 (2)
O1—Sn—C24105.82 (9)C20—C19—H19119.4
C30—Sn—C24121.82 (10)C18—C19—H19119.4
O1—Sn—C1898.06 (8)C21—C20—C19119.4 (3)
C30—Sn—C18110.82 (10)C21—C20—H20120.3
C24—Sn—C18107.86 (10)C19—C20—H20120.3
C2—O1—Sn105.73 (15)C22—C21—C20120.1 (3)
O3—C2—O1120.6 (2)C22—C21—H21119.9
O3—C2—C4122.3 (2)C20—C21—H21119.9
O1—C2—C4117.0 (2)C21—C22—C23120.5 (3)
C5—C4—C9119.0 (2)C21—C22—H22119.7
C5—C4—C2118.0 (2)C23—C22—H22119.7
C9—C4—C2123.0 (2)C18—C23—C22120.2 (2)
C6—C5—C4120.7 (3)C18—C23—H23119.9
C6—C5—H5119.6C22—C23—H23119.9
C4—C5—H5119.6C29—C24—C25119.2 (3)
C7—C6—C5119.8 (3)C29—C24—Sn122.4 (2)
C7—C6—H6120.1C25—C24—Sn118.4 (2)
C5—C6—H6120.1C24—C25—C26120.5 (3)
C8—C7—C6120.2 (3)C24—C25—H25119.8
C8—C7—H7119.9C26—C25—H25119.8
C6—C7—H7119.9C27—C26—C25119.9 (3)
C7—C8—C9120.8 (3)C27—C26—H26120.0
C7—C8—H8119.6C25—C26—H26120.0
C9—C8—H8119.6C26—C27—C28120.0 (3)
C8—C9—C4119.6 (2)C26—C27—H27120.0
C8—C9—C10116.1 (2)C28—C27—H27120.0
C4—C9—C10124.3 (2)C27—C28—C29120.5 (3)
O11—C10—C12121.5 (3)C27—C28—H28119.8
O11—C10—C9118.9 (2)C29—C28—H28119.8
C12—C10—C9119.3 (2)C24—C29—C28119.9 (3)
C17—C12—C13120.1 (3)C24—C29—H29120.0
C17—C12—C10122.0 (2)C28—C29—H29120.0
C13—C12—C10117.8 (2)C35—C30—C31119.2 (2)
C14—C13—C12119.8 (3)C35—C30—Sn118.8 (2)
C14—C13—H13120.1C31—C30—Sn122.05 (18)
C12—C13—H13120.1C32—C31—C30120.1 (3)
C15—C14—C13119.9 (3)C32—C31—H31119.9
C15—C14—H14120.1C30—C31—H31119.9
C13—C14—H14120.1C33—C32—C31120.0 (3)
C16—C15—C14120.7 (3)C33—C32—H32120.0
C16—C15—H15119.6C31—C32—H32120.0
C14—C15—H15119.6C34—C33—C32120.4 (3)
C15—C16—C17119.5 (3)C34—C33—H33119.8
C15—C16—H16120.2C32—C33—H33119.8
C17—C16—H16120.2C33—C34—C35119.7 (3)
C12—C17—C16120.0 (3)C33—C34—H34120.1
C12—C17—H17120.0C35—C34—H34120.1
C16—C17—H17120.0C34—C35—C30120.5 (3)
C23—C18—C19118.6 (2)C34—C35—H35119.7
C23—C18—Sn123.01 (19)C30—C35—H35119.7
C19—C18—Sn118.27 (18)
C30—Sn—O1—C270.89 (16)O1—Sn—C18—C19172.20 (19)
C24—Sn—O1—C262.27 (17)C30—Sn—C18—C1973.0 (2)
C18—Sn—O1—C2173.50 (15)C24—Sn—C18—C1962.6 (2)
Sn—O1—C2—O36.5 (3)C23—C18—C19—C200.5 (4)
Sn—O1—C2—C4171.63 (17)Sn—C18—C19—C20176.01 (19)
O3—C2—C4—C511.1 (4)C18—C19—C20—C210.5 (4)
O1—C2—C4—C5170.8 (2)C19—C20—C21—C220.0 (4)
O3—C2—C4—C9169.3 (2)C20—C21—C22—C230.6 (4)
O1—C2—C4—C98.8 (3)C19—C18—C23—C220.1 (4)
C9—C4—C5—C61.2 (4)Sn—C18—C23—C22175.2 (2)
C2—C4—C5—C6179.2 (2)C21—C22—C23—C180.7 (4)
C4—C5—C6—C70.9 (4)O1—Sn—C24—C29108.6 (2)
C5—C6—C7—C80.1 (4)C30—Sn—C24—C2917.5 (3)
C6—C7—C8—C90.8 (4)C18—Sn—C24—C29147.3 (2)
C7—C8—C9—C40.5 (4)O1—Sn—C24—C2568.8 (2)
C7—C8—C9—C10179.4 (2)C30—Sn—C24—C25165.1 (2)
C5—C4—C9—C80.5 (4)C18—Sn—C24—C2535.3 (3)
C2—C4—C9—C8179.9 (2)C29—C24—C25—C260.6 (5)
C5—C4—C9—C10179.5 (2)Sn—C24—C25—C26176.9 (3)
C2—C4—C9—C100.0 (4)C24—C25—C26—C271.1 (6)
C8—C9—C10—O1168.1 (3)C25—C26—C27—C280.5 (6)
C4—C9—C10—O11112.0 (3)C26—C27—C28—C290.7 (6)
C8—C9—C10—C12105.6 (3)C25—C24—C29—C280.6 (5)
C4—C9—C10—C1274.3 (3)Sn—C24—C29—C28178.0 (2)
O11—C10—C12—C17171.5 (3)C27—C28—C29—C241.3 (5)
C9—C10—C12—C172.1 (4)O1—Sn—C30—C35101.8 (2)
O11—C10—C12—C135.7 (4)C24—Sn—C30—C35133.9 (2)
C9—C10—C12—C13179.3 (2)C18—Sn—C30—C355.4 (2)
C17—C12—C13—C141.2 (4)O1—Sn—C30—C3178.5 (2)
C10—C12—C13—C14178.4 (3)C24—Sn—C30—C3145.8 (2)
C12—C13—C14—C151.4 (4)C18—Sn—C30—C31174.3 (2)
C13—C14—C15—C160.9 (5)C35—C30—C31—C320.1 (4)
C14—C15—C16—C170.0 (4)Sn—C30—C31—C32179.8 (2)
C13—C12—C17—C160.4 (4)C30—C31—C32—C331.1 (5)
C10—C12—C17—C16177.5 (2)C31—C32—C33—C341.3 (5)
C15—C16—C17—C120.2 (4)C32—C33—C34—C350.2 (5)
O1—Sn—C18—C233.1 (2)C33—C34—C35—C301.1 (5)
C30—Sn—C18—C23111.6 (2)C31—C30—C35—C341.2 (4)
C24—Sn—C18—C23112.7 (2)Sn—C30—C35—C34179.0 (2)
 

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