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The crystal structure of the title compound, [Sn(CH3)3(C15H15O2)], is composed of polymeric chains of monomers, linked by secondary coordinating bonds from the O atoms of the hydroxyl group to the Sn atoms, with an Sn...O distance of 2.646 (2) Å. This additional bond leads to a distorted trigonal–bipyramidal geometry around the Sn atom, with three methyl C atoms in equatorial and two O atoms in axial positions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806003941/hk6081sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806003941/hk6081Isup2.hkl
Contains datablock I

CCDC reference: 601194

Key indicators

  • Single-crystal X-ray study
  • T = 233 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.018
  • wR factor = 0.045
  • Data-to-parameter ratio = 18.5

checkCIF/PLATON results

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Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sn1
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.49 From the CIF: _reflns_number_total 3667 Count of symmetry unique reflns 2134 Completeness (_total/calc) 171.84% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1533 Fraction of Friedel pairs measured 0.718 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997), SCALEPACK and SORTAV (Blessing, 1995); 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: SHELXL97.

{4-[1-(4-Hydroxyphenyl)-1-methylethyl]phenoxy}trimethyltin(IV) top
Crystal data top
[Sn(CH3)3(C15H15O2)]F(000) = 792
Mr = 391.06Dx = 1.470 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 12075 reflections
a = 12.6228 (3) Åθ = 1.0–27.5°
b = 13.0820 (3) ŵ = 1.45 mm1
c = 10.7032 (2) ÅT = 233 K
V = 1767.44 (7) Å3Plate, colorless
Z = 40.35 × 0.35 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer
3667 independent reflections
Radiation source: fine-focus sealed tube3566 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
from symmetry-related measurements (Blessing, 1995)
h = 1616
Tmin = 0.663, Tmax = 0.844k = 1616
18702 measured reflectionsl = 1113
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.018 w = 1/[σ2(Fo2) + (0.0225P)2 + 0.5157P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.045(Δ/σ)max = 0.041
S = 1.05Δρmax = 0.43 e Å3
3667 reflectionsΔρmin = 0.43 e Å3
198 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0081 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1537 Friedel Pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.042 (17)
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
Sn10.554597 (8)0.413118 (8)1.01145 (3)0.02656 (6)
O10.49848 (15)0.39645 (12)0.82846 (15)0.0375 (4)
O20.11385 (12)0.05051 (13)0.24442 (15)0.0345 (3)
H2O0.077 (2)0.007 (2)0.274 (3)0.055 (9)*
C10.5993 (2)0.56712 (17)0.9812 (2)0.0423 (7)
H1A0.63910.59171.05260.063*
H1B0.53630.60870.97030.063*
H1C0.64290.57150.90680.063*
C20.67615 (19)0.30136 (17)1.0087 (4)0.0493 (6)
H2A0.65400.24231.05700.074*
H2B0.74020.32981.04480.074*
H2C0.68990.28080.92320.074*
C30.4118 (2)0.3775 (3)1.1052 (3)0.0572 (8)
H3A0.37210.43981.12030.086*
H3B0.42780.34481.18430.086*
H3C0.36990.33151.05410.086*
C40.52402 (19)0.07257 (17)0.4716 (2)0.0320 (5)
C50.6029 (2)0.0968 (2)0.3654 (3)0.0504 (7)
H5A0.60180.04190.30440.076*
H5B0.67370.10330.39970.076*
H5C0.58280.16040.32520.076*
C60.55909 (19)0.0274 (2)0.5337 (3)0.0540 (10)
H6A0.56050.08160.47190.081*
H6B0.50970.04510.59970.081*
H6C0.62930.01880.56890.081*
C70.52198 (17)0.15671 (16)0.5706 (2)0.0279 (4)
C80.43854 (16)0.16295 (19)0.6552 (2)0.0321 (5)
H80.38470.11340.65170.039*
C90.43196 (16)0.23926 (18)0.7440 (2)0.0318 (5)
H90.37440.24070.79960.038*
C100.50989 (17)0.31385 (16)0.7516 (2)0.0304 (4)
C110.59741 (17)0.30622 (19)0.6728 (2)0.0365 (5)
H110.65310.35360.67960.044*
C120.60275 (17)0.22868 (18)0.5840 (2)0.0351 (5)
H120.66240.22470.53160.042*
C130.41406 (17)0.06265 (17)0.4104 (2)0.0274 (4)
C140.36062 (19)0.15008 (16)0.3724 (2)0.0344 (5)
H140.39260.21420.38490.041*
C150.26210 (19)0.14581 (16)0.3168 (2)0.0347 (5)
H150.22800.20640.29200.042*
C160.21344 (16)0.05226 (17)0.29759 (19)0.0280 (4)
C170.26671 (18)0.03585 (16)0.3298 (2)0.0361 (5)
H170.23600.10000.31380.043*
C180.36611 (18)0.02995 (16)0.3860 (2)0.0351 (5)
H180.40140.09070.40770.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.02748 (8)0.02622 (8)0.02598 (8)0.00094 (4)0.00327 (8)0.00265 (9)
O10.0481 (10)0.0369 (8)0.0276 (9)0.0124 (7)0.0106 (7)0.0089 (7)
O20.0311 (8)0.0385 (9)0.0339 (8)0.0056 (7)0.0061 (7)0.0084 (7)
C10.0586 (15)0.0306 (10)0.0377 (18)0.0083 (10)0.0088 (11)0.0029 (9)
C20.0547 (12)0.0446 (11)0.0485 (12)0.0215 (10)0.0166 (18)0.0132 (19)
C30.0466 (15)0.086 (2)0.0396 (15)0.0250 (16)0.0025 (13)0.0020 (16)
C40.0290 (10)0.0381 (11)0.0289 (12)0.0036 (9)0.0048 (8)0.0069 (8)
C50.0327 (13)0.078 (2)0.0402 (15)0.0039 (11)0.0053 (11)0.0271 (13)
C60.0601 (15)0.0430 (13)0.059 (3)0.0229 (10)0.0260 (14)0.0140 (15)
C70.0280 (10)0.0304 (11)0.0254 (10)0.0037 (8)0.0061 (8)0.0020 (9)
C80.0327 (12)0.0318 (12)0.0318 (12)0.0005 (8)0.0003 (8)0.0000 (10)
C90.0330 (11)0.0364 (12)0.0260 (11)0.0051 (9)0.0037 (8)0.0023 (9)
C100.0365 (11)0.0325 (10)0.0222 (10)0.0085 (9)0.0097 (9)0.0030 (8)
C110.0299 (11)0.0416 (12)0.0378 (13)0.0048 (9)0.0054 (9)0.0084 (10)
C120.0285 (11)0.0442 (13)0.0326 (12)0.0007 (9)0.0003 (9)0.0090 (10)
C130.0305 (10)0.0271 (9)0.0246 (11)0.0012 (9)0.0028 (9)0.0025 (8)
C140.0450 (13)0.0204 (9)0.0378 (12)0.0003 (9)0.0112 (10)0.0045 (9)
C150.0444 (12)0.0235 (10)0.0361 (12)0.0044 (9)0.0119 (10)0.0019 (9)
C160.0293 (10)0.0328 (10)0.0220 (10)0.0017 (8)0.0012 (8)0.0012 (8)
C170.0363 (11)0.0247 (10)0.0472 (13)0.0069 (8)0.0051 (10)0.0042 (10)
C180.0353 (11)0.0239 (9)0.0459 (13)0.0018 (8)0.0035 (10)0.0048 (9)
Geometric parameters (Å, º) top
Sn1—O12.094 (2)C6—H6A0.9700
Sn1—C12.117 (2)C6—H6B0.9700
Sn1—C22.120 (2)C6—H6C0.9700
Sn1—C32.115 (3)C7—C81.391 (3)
Sn1—O2i2.646 (2)C7—C121.395 (3)
O1—C101.366 (3)C8—C91.381 (3)
O2—H2O0.80 (2)C8—H80.9400
O2—C161.380 (3)C9—C101.388 (3)
C1—H1A0.9700C9—H90.9400
C1—H1B0.9700C10—C111.394 (3)
C1—H1C0.9700C11—C121.392 (3)
C2—H2A0.9700C11—H110.9400
C2—H2B0.9700C12—H120.9400
C2—H2C0.9700C13—C181.379 (3)
C3—H3A0.9700C13—C141.389 (3)
C3—H3B0.9700C14—C151.380 (3)
C3—H3C0.9700C14—H140.9400
C4—C71.528 (3)C15—C161.385 (3)
C4—C61.533 (4)C15—H150.9400
C4—C131.540 (3)C16—C171.378 (3)
C4—C51.545 (4)C17—C181.393 (3)
C5—H5A0.9700C17—H170.9400
C5—H5B0.9700C18—H180.9400
C5—H5C0.9700
O1—Sn1—O2i174.6 (1)C4—C6—H6A109.5
O1—Sn1—C192.6 (1)C4—C6—H6B109.5
O1—Sn1—C299.2 (1)H6A—C6—H6B109.5
O1—Sn1—C397.6 (1)C4—C6—H6C109.5
C1—Sn1—O2i84.1 (1)H6A—C6—H6C109.5
C2—Sn1—O2i86.1 (1)H6B—C6—H6C109.5
C3—Sn1—O2i80.4 (1)C8—C7—C12116.6 (2)
C1—Sn1—C2117.5 (1)C8—C7—C4120.4 (2)
C1—Sn1—C3120.6 (1)C12—C7—C4123.0 (2)
C2—Sn1—C3118.1 (1)C9—C8—C7122.4 (2)
C10—O1—Sn1127.6 (1)C9—C8—H8118.8
C16—O2—H2O113 (2)C7—C8—H8118.8
Sn1—C1—H1A109.5C8—C9—C10120.4 (2)
Sn1—C1—H1B109.5C8—C9—H9119.8
H1A—C1—H1B109.5C10—C9—H9119.8
Sn1—C1—H1C109.5O1—C10—C9121.1 (2)
H1A—C1—H1C109.5O1—C10—C11120.3 (2)
H1B—C1—H1C109.5C9—C10—C11118.4 (2)
Sn1—C2—H2A109.5C12—C11—C10120.3 (2)
Sn1—C2—H2B109.5C12—C11—H11119.9
H2A—C2—H2B109.5C10—C11—H11119.9
Sn1—C2—H2C109.5C11—C12—C7121.8 (2)
H2A—C2—H2C109.5C11—C12—H12119.1
H2B—C2—H2C109.5C7—C12—H12119.1
Sn1—C3—H3A109.5C18—C13—C14117.0 (2)
Sn1—C3—H3B109.5C18—C13—C4123.4 (2)
H3A—C3—H3B109.5C14—C13—C4119.5 (2)
Sn1—C3—H3C109.5C15—C14—C13122.1 (2)
H3A—C3—H3C109.5C15—C14—H14119.0
H3B—C3—H3C109.5C13—C14—H14119.0
C7—C4—C6108.6 (2)C14—C15—C16120.0 (2)
C7—C4—C13109.9 (2)C14—C15—H15120.0
C6—C4—C13111.9 (2)C16—C15—H15120.0
C7—C4—C5111.9 (2)C17—C16—O2122.3 (2)
C6—C4—C5108.0 (2)C17—C16—C15119.1 (2)
C13—C4—C5106.6 (2)O2—C16—C15118.7 (2)
C4—C5—H5A109.5C16—C17—C18120.1 (2)
C4—C5—H5B109.5C16—C17—H17120.0
H5A—C5—H5B109.5C18—C17—H17120.0
C4—C5—H5C109.5C13—C18—C17121.7 (2)
H5A—C5—H5C109.5C13—C18—H18119.1
H5B—C5—H5C109.5C17—C18—H18119.1
Symmetry code: (i) x+1/2, y+1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O1ii0.78 (2)1.83 (3)2.623 (2)174 (3)
Symmetry code: (ii) x+1/2, y1/2, z1/2.
 

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