The crystal structure of the title compound, [Sn(CH
3)
3(C
15H
15O
2)], 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
CCDC reference: 601194
Key indicators
- Single-crystal X-ray study
- T = 233 K
- Mean (C-C) = 0.003 Å
- R factor = 0.018
- wR factor = 0.045
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
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
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 = 391.06 | Dx = 1.470 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 12075 reflections |
a = 12.6228 (3) Å | θ = 1.0–27.5° |
b = 13.0820 (3) Å | µ = 1.45 mm−1 |
c = 10.7032 (2) Å | T = 233 K |
V = 1767.44 (7) Å3 | Plate, colorless |
Z = 4 | 0.35 × 0.35 × 0.12 mm |
Data collection top
Nonius KappaCCD diffractometer | 3667 independent reflections |
Radiation source: fine-focus sealed tube | 3566 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan from symmetry-related measurements (Blessing, 1995) | h = −16→16 |
Tmin = 0.663, Tmax = 0.844 | k = −16→16 |
18702 measured reflections | l = −11→13 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H 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 = 1.05 | Δρmax = 0.43 e Å−3 |
3667 reflections | Δρmin = −0.43 e Å−3 |
198 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0081 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1537 Friedel Pairs |
Secondary atom site location: difference Fourier map | Absolute 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 | x | y | z | Uiso*/Ueq | |
Sn1 | 0.554597 (8) | 0.413118 (8) | 1.01145 (3) | 0.02656 (6) | |
O1 | 0.49848 (15) | 0.39645 (12) | 0.82846 (15) | 0.0375 (4) | |
O2 | 0.11385 (12) | 0.05051 (13) | 0.24442 (15) | 0.0345 (3) | |
H2O | 0.077 (2) | 0.007 (2) | 0.274 (3) | 0.055 (9)* | |
C1 | 0.5993 (2) | 0.56712 (17) | 0.9812 (2) | 0.0423 (7) | |
H1A | 0.6391 | 0.5917 | 1.0526 | 0.063* | |
H1B | 0.5363 | 0.6087 | 0.9703 | 0.063* | |
H1C | 0.6429 | 0.5715 | 0.9068 | 0.063* | |
C2 | 0.67615 (19) | 0.30136 (17) | 1.0087 (4) | 0.0493 (6) | |
H2A | 0.6540 | 0.2423 | 1.0570 | 0.074* | |
H2B | 0.7402 | 0.3298 | 1.0448 | 0.074* | |
H2C | 0.6899 | 0.2808 | 0.9232 | 0.074* | |
C3 | 0.4118 (2) | 0.3775 (3) | 1.1052 (3) | 0.0572 (8) | |
H3A | 0.3721 | 0.4398 | 1.1203 | 0.086* | |
H3B | 0.4278 | 0.3448 | 1.1843 | 0.086* | |
H3C | 0.3699 | 0.3315 | 1.0541 | 0.086* | |
C4 | 0.52402 (19) | 0.07257 (17) | 0.4716 (2) | 0.0320 (5) | |
C5 | 0.6029 (2) | 0.0968 (2) | 0.3654 (3) | 0.0504 (7) | |
H5A | 0.6018 | 0.0419 | 0.3044 | 0.076* | |
H5B | 0.6737 | 0.1033 | 0.3997 | 0.076* | |
H5C | 0.5828 | 0.1604 | 0.3252 | 0.076* | |
C6 | 0.55909 (19) | −0.0274 (2) | 0.5337 (3) | 0.0540 (10) | |
H6A | 0.5605 | −0.0816 | 0.4719 | 0.081* | |
H6B | 0.5097 | −0.0451 | 0.5997 | 0.081* | |
H6C | 0.6293 | −0.0188 | 0.5689 | 0.081* | |
C7 | 0.52198 (17) | 0.15671 (16) | 0.5706 (2) | 0.0279 (4) | |
C8 | 0.43854 (16) | 0.16295 (19) | 0.6552 (2) | 0.0321 (5) | |
H8 | 0.3847 | 0.1134 | 0.6517 | 0.039* | |
C9 | 0.43196 (16) | 0.23926 (18) | 0.7440 (2) | 0.0318 (5) | |
H9 | 0.3744 | 0.2407 | 0.7996 | 0.038* | |
C10 | 0.50989 (17) | 0.31385 (16) | 0.7516 (2) | 0.0304 (4) | |
C11 | 0.59741 (17) | 0.30622 (19) | 0.6728 (2) | 0.0365 (5) | |
H11 | 0.6531 | 0.3536 | 0.6796 | 0.044* | |
C12 | 0.60275 (17) | 0.22868 (18) | 0.5840 (2) | 0.0351 (5) | |
H12 | 0.6624 | 0.2247 | 0.5316 | 0.042* | |
C13 | 0.41406 (17) | 0.06265 (17) | 0.4104 (2) | 0.0274 (4) | |
C14 | 0.36062 (19) | 0.15008 (16) | 0.3724 (2) | 0.0344 (5) | |
H14 | 0.3926 | 0.2142 | 0.3849 | 0.041* | |
C15 | 0.26210 (19) | 0.14581 (16) | 0.3168 (2) | 0.0347 (5) | |
H15 | 0.2280 | 0.2064 | 0.2920 | 0.042* | |
C16 | 0.21344 (16) | 0.05226 (17) | 0.29759 (19) | 0.0280 (4) | |
C17 | 0.26671 (18) | −0.03585 (16) | 0.3298 (2) | 0.0361 (5) | |
H17 | 0.2360 | −0.1000 | 0.3138 | 0.043* | |
C18 | 0.36611 (18) | −0.02995 (16) | 0.3860 (2) | 0.0351 (5) | |
H18 | 0.4014 | −0.0907 | 0.4077 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sn1 | 0.02748 (8) | 0.02622 (8) | 0.02598 (8) | 0.00094 (4) | −0.00327 (8) | −0.00265 (9) |
O1 | 0.0481 (10) | 0.0369 (8) | 0.0276 (9) | 0.0124 (7) | −0.0106 (7) | −0.0089 (7) |
O2 | 0.0311 (8) | 0.0385 (9) | 0.0339 (8) | −0.0056 (7) | −0.0061 (7) | 0.0084 (7) |
C1 | 0.0586 (15) | 0.0306 (10) | 0.0377 (18) | −0.0083 (10) | 0.0088 (11) | −0.0029 (9) |
C2 | 0.0547 (12) | 0.0446 (11) | 0.0485 (12) | 0.0215 (10) | −0.0166 (18) | −0.0132 (19) |
C3 | 0.0466 (15) | 0.086 (2) | 0.0396 (15) | −0.0250 (16) | 0.0025 (13) | −0.0020 (16) |
C4 | 0.0290 (10) | 0.0381 (11) | 0.0289 (12) | 0.0036 (9) | −0.0048 (8) | −0.0069 (8) |
C5 | 0.0327 (13) | 0.078 (2) | 0.0402 (15) | −0.0039 (11) | 0.0053 (11) | −0.0271 (13) |
C6 | 0.0601 (15) | 0.0430 (13) | 0.059 (3) | 0.0229 (10) | −0.0260 (14) | −0.0140 (15) |
C7 | 0.0280 (10) | 0.0304 (11) | 0.0254 (10) | 0.0037 (8) | −0.0061 (8) | −0.0020 (9) |
C8 | 0.0327 (12) | 0.0318 (12) | 0.0318 (12) | −0.0005 (8) | −0.0003 (8) | 0.0000 (10) |
C9 | 0.0330 (11) | 0.0364 (12) | 0.0260 (11) | 0.0051 (9) | 0.0037 (8) | 0.0023 (9) |
C10 | 0.0365 (11) | 0.0325 (10) | 0.0222 (10) | 0.0085 (9) | −0.0097 (9) | −0.0030 (8) |
C11 | 0.0299 (11) | 0.0416 (12) | 0.0378 (13) | −0.0048 (9) | −0.0054 (9) | −0.0084 (10) |
C12 | 0.0285 (11) | 0.0442 (13) | 0.0326 (12) | −0.0007 (9) | 0.0003 (9) | −0.0090 (10) |
C13 | 0.0305 (10) | 0.0271 (9) | 0.0246 (11) | 0.0012 (9) | −0.0028 (9) | −0.0025 (8) |
C14 | 0.0450 (13) | 0.0204 (9) | 0.0378 (12) | 0.0003 (9) | −0.0112 (10) | −0.0045 (9) |
C15 | 0.0444 (12) | 0.0235 (10) | 0.0361 (12) | 0.0044 (9) | −0.0119 (10) | −0.0019 (9) |
C16 | 0.0293 (10) | 0.0328 (10) | 0.0220 (10) | −0.0017 (8) | −0.0012 (8) | 0.0012 (8) |
C17 | 0.0363 (11) | 0.0247 (10) | 0.0472 (13) | −0.0069 (8) | −0.0051 (10) | 0.0042 (10) |
C18 | 0.0353 (11) | 0.0239 (9) | 0.0459 (13) | 0.0018 (8) | −0.0035 (10) | 0.0048 (9) |
Geometric parameters (Å, º) top
Sn1—O1 | 2.094 (2) | C6—H6A | 0.9700 |
Sn1—C1 | 2.117 (2) | C6—H6B | 0.9700 |
Sn1—C2 | 2.120 (2) | C6—H6C | 0.9700 |
Sn1—C3 | 2.115 (3) | C7—C8 | 1.391 (3) |
Sn1—O2i | 2.646 (2) | C7—C12 | 1.395 (3) |
O1—C10 | 1.366 (3) | C8—C9 | 1.381 (3) |
O2—H2O | 0.80 (2) | C8—H8 | 0.9400 |
O2—C16 | 1.380 (3) | C9—C10 | 1.388 (3) |
C1—H1A | 0.9700 | C9—H9 | 0.9400 |
C1—H1B | 0.9700 | C10—C11 | 1.394 (3) |
C1—H1C | 0.9700 | C11—C12 | 1.392 (3) |
C2—H2A | 0.9700 | C11—H11 | 0.9400 |
C2—H2B | 0.9700 | C12—H12 | 0.9400 |
C2—H2C | 0.9700 | C13—C18 | 1.379 (3) |
C3—H3A | 0.9700 | C13—C14 | 1.389 (3) |
C3—H3B | 0.9700 | C14—C15 | 1.380 (3) |
C3—H3C | 0.9700 | C14—H14 | 0.9400 |
C4—C7 | 1.528 (3) | C15—C16 | 1.385 (3) |
C4—C6 | 1.533 (4) | C15—H15 | 0.9400 |
C4—C13 | 1.540 (3) | C16—C17 | 1.378 (3) |
C4—C5 | 1.545 (4) | C17—C18 | 1.393 (3) |
C5—H5A | 0.9700 | C17—H17 | 0.9400 |
C5—H5B | 0.9700 | C18—H18 | 0.9400 |
C5—H5C | 0.9700 | | |
| | | |
O1—Sn1—O2i | 174.6 (1) | C4—C6—H6A | 109.5 |
O1—Sn1—C1 | 92.6 (1) | C4—C6—H6B | 109.5 |
O1—Sn1—C2 | 99.2 (1) | H6A—C6—H6B | 109.5 |
O1—Sn1—C3 | 97.6 (1) | C4—C6—H6C | 109.5 |
C1—Sn1—O2i | 84.1 (1) | H6A—C6—H6C | 109.5 |
C2—Sn1—O2i | 86.1 (1) | H6B—C6—H6C | 109.5 |
C3—Sn1—O2i | 80.4 (1) | C8—C7—C12 | 116.6 (2) |
C1—Sn1—C2 | 117.5 (1) | C8—C7—C4 | 120.4 (2) |
C1—Sn1—C3 | 120.6 (1) | C12—C7—C4 | 123.0 (2) |
C2—Sn1—C3 | 118.1 (1) | C9—C8—C7 | 122.4 (2) |
C10—O1—Sn1 | 127.6 (1) | C9—C8—H8 | 118.8 |
C16—O2—H2O | 113 (2) | C7—C8—H8 | 118.8 |
Sn1—C1—H1A | 109.5 | C8—C9—C10 | 120.4 (2) |
Sn1—C1—H1B | 109.5 | C8—C9—H9 | 119.8 |
H1A—C1—H1B | 109.5 | C10—C9—H9 | 119.8 |
Sn1—C1—H1C | 109.5 | O1—C10—C9 | 121.1 (2) |
H1A—C1—H1C | 109.5 | O1—C10—C11 | 120.3 (2) |
H1B—C1—H1C | 109.5 | C9—C10—C11 | 118.4 (2) |
Sn1—C2—H2A | 109.5 | C12—C11—C10 | 120.3 (2) |
Sn1—C2—H2B | 109.5 | C12—C11—H11 | 119.9 |
H2A—C2—H2B | 109.5 | C10—C11—H11 | 119.9 |
Sn1—C2—H2C | 109.5 | C11—C12—C7 | 121.8 (2) |
H2A—C2—H2C | 109.5 | C11—C12—H12 | 119.1 |
H2B—C2—H2C | 109.5 | C7—C12—H12 | 119.1 |
Sn1—C3—H3A | 109.5 | C18—C13—C14 | 117.0 (2) |
Sn1—C3—H3B | 109.5 | C18—C13—C4 | 123.4 (2) |
H3A—C3—H3B | 109.5 | C14—C13—C4 | 119.5 (2) |
Sn1—C3—H3C | 109.5 | C15—C14—C13 | 122.1 (2) |
H3A—C3—H3C | 109.5 | C15—C14—H14 | 119.0 |
H3B—C3—H3C | 109.5 | C13—C14—H14 | 119.0 |
C7—C4—C6 | 108.6 (2) | C14—C15—C16 | 120.0 (2) |
C7—C4—C13 | 109.9 (2) | C14—C15—H15 | 120.0 |
C6—C4—C13 | 111.9 (2) | C16—C15—H15 | 120.0 |
C7—C4—C5 | 111.9 (2) | C17—C16—O2 | 122.3 (2) |
C6—C4—C5 | 108.0 (2) | C17—C16—C15 | 119.1 (2) |
C13—C4—C5 | 106.6 (2) | O2—C16—C15 | 118.7 (2) |
C4—C5—H5A | 109.5 | C16—C17—C18 | 120.1 (2) |
C4—C5—H5B | 109.5 | C16—C17—H17 | 120.0 |
H5A—C5—H5B | 109.5 | C18—C17—H17 | 120.0 |
C4—C5—H5C | 109.5 | C13—C18—C17 | 121.7 (2) |
H5A—C5—H5C | 109.5 | C13—C18—H18 | 119.1 |
H5B—C5—H5C | 109.5 | C17—C18—H18 | 119.1 |
Symmetry code: (i) x+1/2, −y+1/2, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2O···O1ii | 0.78 (2) | 1.83 (3) | 2.623 (2) | 174 (3) |
Symmetry code: (ii) −x+1/2, y−1/2, z−1/2. |