Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015449/hb2357sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015449/hb2357Isup2.hkl |
CCDC reference: 646601
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.026
- wR factor = 0.067
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.82 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.40 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C37
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Bis[tris(2-phenyl-2-methylpropyl)tin] oxide (1.05 g, 1 mmol) was condensed with 4-hydroxyphenylethanone (0.27 g, 2 mmol) in toluene (50 ml). Water was removed with a Dean–Stark water separator. The resulting clear solution was evaporated to dryness using a rotary evaporator. The white solid obtained was recrystallized from ethanol and crystals of (I) were obtained from cyclohexane by slow evaporation at 298 K (yield 78%; m.p. 358–359 K).
The H atoms were placed at calculated positions (C—H = 0.93–0.97 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Little attention has been paid to the condensation reaction of tris(2-methyl-2-phenylpropyl)tin oxide, {[C6H5C(CH3)2CH2]3Sn}2O, an industrial miticide, with phenols in the literature. In two reported structures, tris(2-methyl-2-phenylpropyl)tin pentachlorophenoate (Zhang et al., 2002) and tris(2-methyl-2-phenylpropyl)tin 4-nitrophenolate (Yang et al., 2006), the tin atom is four coordinated.
In the title compound, (I), the Sn atom is also four-coordinate and possess a distorted SnOC3 tetrahedral geometry (Fig. 1 & Table 1). This is different from Me3SnOMe, in which almost planar trimethyltin groups are linked by two methoxy ligands forming infinite one-dimensional zigzag chains with nearly ideally trigonal-bipyramidal coordinated tin atom (Domingos & Sheldrick, 1974), due to the crowding of the four bulky groups at the Sn atom in (I). The Sn—C distances lie in the narrow range of 2.144 (2)–2.157 (2) Å, in agreement with those [2.142 (2)–2.158 (2) Å] in tris(2-methyl-2-phenylpropyl)tin 4-nitrophenolate (Yang et al., 2006), but slightly longer than those [2.105 (4)–2.114 (4) Å] in tris(2-methyl-2-phenylpropyl)tin pentachlorophenoate (Zhang et al., 2002). The Sn—O separation in (I) of 2.045 (2) Å is almost same as that of tris(2-methyl-2-phenylpropyl)tin 4-nitrophenolate and shorter than that [2.103 (3) Å] found in tris(2-methyl-2-phenylpropyl)tin pentachlorophenoate.
For related complexes containing the tris(2-methyl-2-phenylpropyl)tin fragment and a distorted tetrahedral SnOC3 grouping, see Domingos & Sheldrick (1974), Zhang et al. (2002) and Yang et al. (2006).
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity. |
[Sn(C10H13)3(C8H7O2)] | Z = 2 |
Mr = 653.44 | F(000) = 680 |
Triclinic, P1 | Dx = 1.288 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5062 (7) Å | Cell parameters from 7970 reflections |
b = 9.7309 (7) Å | θ = 2.2–26.4° |
c = 19.0769 (15) Å | µ = 0.79 mm−1 |
α = 78.704 (2)° | T = 295 K |
β = 87.906 (1)° | Block, colorless |
γ = 76.874 (1)° | 0.41 × 0.30 × 0.22 mm |
V = 1685.2 (2) Å3 |
Bruker SMART APEX CCD diffractometer | 6532 independent reflections |
Radiation source: fine-focus sealed tube | 6022 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 26.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→11 |
Tmin = 0.738, Tmax = 0.846 | k = −11→11 |
13220 measured reflections | l = −23→23 |
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)] = 0.026 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0402P)2 + 0.0822P] where P = (Fo2 + 2Fc2)/3 |
6532 reflections | (Δ/σ)max < 0.001 |
371 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
[Sn(C10H13)3(C8H7O2)] | γ = 76.874 (1)° |
Mr = 653.44 | V = 1685.2 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.5062 (7) Å | Mo Kα radiation |
b = 9.7309 (7) Å | µ = 0.79 mm−1 |
c = 19.0769 (15) Å | T = 295 K |
α = 78.704 (2)° | 0.41 × 0.30 × 0.22 mm |
β = 87.906 (1)° |
Bruker SMART APEX CCD diffractometer | 6532 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 6022 reflections with I > 2σ(I) |
Tmin = 0.738, Tmax = 0.846 | Rint = 0.017 |
13220 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | 0 restraints |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.43 e Å−3 |
6532 reflections | Δρmin = −0.29 e Å−3 |
371 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.317898 (13) | 0.629091 (14) | 0.227412 (7) | 0.03998 (6) | |
O1 | 0.52017 (16) | 0.51431 (17) | 0.21076 (8) | 0.0568 (4) | |
O2 | 0.9387 (3) | −0.0669 (3) | 0.35029 (17) | 0.1349 (11) | |
C1 | 0.3299 (2) | 0.7556 (2) | 0.30715 (11) | 0.0472 (5) | |
H1A | 0.2319 | 0.7952 | 0.3205 | 0.057* | |
H1B | 0.3767 | 0.6905 | 0.3492 | 0.057* | |
C2 | 0.4082 (2) | 0.8807 (2) | 0.28908 (12) | 0.0507 (5) | |
C3 | 0.5696 (3) | 0.8193 (3) | 0.28176 (17) | 0.0736 (7) | |
H3A | 0.6058 | 0.7540 | 0.3251 | 0.110* | |
H3B | 0.6196 | 0.8962 | 0.2729 | 0.110* | |
H3C | 0.5850 | 0.7689 | 0.2426 | 0.110* | |
C4 | 0.3876 (3) | 0.9623 (3) | 0.35178 (15) | 0.0777 (8) | |
H4A | 0.2866 | 1.0026 | 0.3570 | 0.117* | |
H4B | 0.4391 | 1.0381 | 0.3422 | 0.117* | |
H4C | 0.4241 | 0.8970 | 0.3951 | 0.117* | |
C5 | 0.3417 (2) | 0.9854 (2) | 0.22192 (12) | 0.0498 (5) | |
C6 | 0.4219 (3) | 1.0272 (3) | 0.16242 (16) | 0.0725 (7) | |
H6 | 0.5218 | 0.9949 | 0.1637 | 0.087* | |
C7 | 0.3552 (4) | 1.1164 (3) | 0.10115 (17) | 0.0879 (9) | |
H7 | 0.4113 | 1.1424 | 0.0620 | 0.106* | |
C8 | 0.2095 (4) | 1.1667 (3) | 0.09735 (16) | 0.0827 (9) | |
H8 | 0.1654 | 1.2243 | 0.0557 | 0.099* | |
C9 | 0.1297 (3) | 1.1309 (3) | 0.15570 (15) | 0.0738 (7) | |
H9 | 0.0304 | 1.1674 | 0.1545 | 0.089* | |
C10 | 0.1941 (3) | 1.0405 (3) | 0.21730 (13) | 0.0596 (6) | |
H10 | 0.1367 | 1.0165 | 0.2563 | 0.072* | |
C11 | 0.2938 (2) | 0.7468 (2) | 0.11949 (11) | 0.0474 (5) | |
H11A | 0.2351 | 0.8420 | 0.1204 | 0.057* | |
H11B | 0.3886 | 0.7587 | 0.1027 | 0.057* | |
C12 | 0.2271 (2) | 0.6850 (2) | 0.06371 (10) | 0.0482 (5) | |
C13 | 0.3191 (3) | 0.5349 (3) | 0.06031 (14) | 0.0693 (7) | |
H13A | 0.4170 | 0.5412 | 0.0493 | 0.104* | |
H13B | 0.2813 | 0.4976 | 0.0238 | 0.104* | |
H13C | 0.3164 | 0.4720 | 0.1056 | 0.104* | |
C14 | 0.2323 (3) | 0.7832 (3) | −0.00954 (12) | 0.0731 (8) | |
H14A | 0.3309 | 0.7852 | −0.0215 | 0.110* | |
H14B | 0.1788 | 0.8788 | −0.0077 | 0.110* | |
H14C | 0.1905 | 0.7470 | −0.0452 | 0.110* | |
C15 | 0.0697 (2) | 0.6840 (2) | 0.08094 (10) | 0.0464 (5) | |
C16 | −0.0250 (3) | 0.8086 (3) | 0.09183 (13) | 0.0612 (6) | |
H16 | 0.0094 | 0.8916 | 0.0894 | 0.073* | |
C17 | −0.1686 (3) | 0.8130 (4) | 0.10622 (16) | 0.0825 (9) | |
H17 | −0.2296 | 0.8982 | 0.1136 | 0.099* | |
C18 | −0.2220 (3) | 0.6928 (5) | 0.10974 (15) | 0.0886 (10) | |
H18 | −0.3192 | 0.6957 | 0.1193 | 0.106* | |
C19 | −0.1318 (4) | 0.5696 (4) | 0.09911 (14) | 0.0828 (9) | |
H19 | −0.1676 | 0.4874 | 0.1019 | 0.099* | |
C20 | 0.0132 (3) | 0.5637 (3) | 0.08411 (12) | 0.0622 (6) | |
H20 | 0.0729 | 0.4783 | 0.0761 | 0.075* | |
C21 | 0.2088 (2) | 0.4559 (2) | 0.25972 (10) | 0.0442 (5) | |
H21A | 0.1647 | 0.4415 | 0.2175 | 0.053* | |
H21B | 0.2814 | 0.3690 | 0.2769 | 0.053* | |
C22 | 0.0910 (2) | 0.4712 (2) | 0.31761 (11) | 0.0438 (4) | |
C23 | 0.0239 (3) | 0.3390 (3) | 0.32729 (14) | 0.0693 (7) | |
H23A | −0.0185 | 0.3358 | 0.2829 | 0.104* | |
H23B | −0.0492 | 0.3454 | 0.3633 | 0.104* | |
H23C | 0.0977 | 0.2533 | 0.3417 | 0.104* | |
C24 | −0.0271 (3) | 0.6045 (3) | 0.29186 (13) | 0.0670 (7) | |
H24A | −0.0663 | 0.5975 | 0.2474 | 0.100* | |
H24B | 0.0129 | 0.6883 | 0.2851 | 0.100* | |
H24C | −0.1022 | 0.6119 | 0.3268 | 0.100* | |
C25 | 0.1581 (2) | 0.4748 (2) | 0.38874 (10) | 0.0426 (4) | |
C26 | 0.2682 (3) | 0.3640 (3) | 0.41985 (13) | 0.0645 (6) | |
H26 | 0.3015 | 0.2863 | 0.3973 | 0.077* | |
C27 | 0.3310 (3) | 0.3660 (4) | 0.48461 (16) | 0.0872 (9) | |
H27 | 0.4052 | 0.2899 | 0.5049 | 0.105* | |
C28 | 0.2841 (4) | 0.4785 (4) | 0.51789 (14) | 0.0861 (9) | |
H28 | 0.3263 | 0.4803 | 0.5608 | 0.103* | |
C29 | 0.1750 (4) | 0.5889 (3) | 0.48842 (14) | 0.0747 (8) | |
H29 | 0.1423 | 0.6660 | 0.5114 | 0.090* | |
C30 | 0.1130 (3) | 0.5872 (3) | 0.42491 (12) | 0.0555 (6) | |
H30 | 0.0384 | 0.6637 | 0.4056 | 0.067* | |
C31 | 0.5915 (2) | 0.3940 (2) | 0.25247 (12) | 0.0483 (5) | |
C32 | 0.6787 (3) | 0.2864 (3) | 0.22104 (14) | 0.0604 (6) | |
H32 | 0.6834 | 0.2983 | 0.1715 | 0.073* | |
C33 | 0.7573 (3) | 0.1634 (3) | 0.26260 (16) | 0.0665 (7) | |
H33 | 0.8155 | 0.0939 | 0.2405 | 0.080* | |
C34 | 0.7522 (2) | 0.1401 (2) | 0.33631 (15) | 0.0591 (6) | |
C35 | 0.6640 (3) | 0.2438 (3) | 0.36739 (14) | 0.0592 (6) | |
H35 | 0.6567 | 0.2292 | 0.4169 | 0.071* | |
C36 | 0.5859 (2) | 0.3697 (3) | 0.32638 (13) | 0.0560 (6) | |
H36 | 0.5287 | 0.4390 | 0.3489 | 0.067* | |
C37 | 0.8452 (3) | 0.0082 (3) | 0.3789 (2) | 0.0812 (9) | |
C38 | 0.8200 (5) | −0.0289 (4) | 0.4578 (2) | 0.1201 (14) | |
H38A | 0.8626 | −0.1287 | 0.4751 | 0.180* | |
H38B | 0.7181 | −0.0108 | 0.4667 | 0.180* | |
H38C | 0.8633 | 0.0291 | 0.4820 | 0.180* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.03956 (9) | 0.04239 (9) | 0.03860 (9) | −0.01044 (6) | −0.00066 (6) | −0.00760 (6) |
O1 | 0.0426 (8) | 0.0607 (10) | 0.0603 (10) | −0.0036 (7) | 0.0056 (7) | −0.0058 (8) |
O2 | 0.123 (2) | 0.0682 (14) | 0.170 (3) | 0.0354 (14) | 0.0357 (19) | 0.0092 (15) |
C1 | 0.0523 (12) | 0.0480 (12) | 0.0415 (11) | −0.0092 (9) | −0.0026 (9) | −0.0108 (9) |
C2 | 0.0508 (12) | 0.0488 (12) | 0.0563 (13) | −0.0123 (10) | −0.0049 (10) | −0.0168 (10) |
C3 | 0.0521 (14) | 0.0729 (17) | 0.101 (2) | −0.0172 (13) | −0.0109 (14) | −0.0222 (15) |
C4 | 0.099 (2) | 0.0668 (17) | 0.0731 (18) | −0.0108 (15) | −0.0217 (15) | −0.0320 (14) |
C5 | 0.0573 (13) | 0.0402 (11) | 0.0569 (13) | −0.0161 (10) | 0.0010 (10) | −0.0155 (9) |
C6 | 0.0704 (17) | 0.0702 (17) | 0.0834 (19) | −0.0322 (14) | 0.0112 (14) | −0.0129 (15) |
C7 | 0.123 (3) | 0.0736 (19) | 0.0697 (19) | −0.043 (2) | 0.0186 (18) | 0.0026 (15) |
C8 | 0.125 (3) | 0.0522 (16) | 0.0641 (18) | −0.0138 (17) | −0.0079 (18) | −0.0007 (13) |
C9 | 0.0839 (19) | 0.0561 (15) | 0.0718 (18) | 0.0042 (14) | −0.0120 (15) | −0.0105 (13) |
C10 | 0.0654 (15) | 0.0547 (14) | 0.0554 (14) | −0.0044 (11) | 0.0005 (11) | −0.0132 (11) |
C11 | 0.0488 (12) | 0.0508 (12) | 0.0437 (11) | −0.0172 (10) | 0.0016 (9) | −0.0046 (9) |
C12 | 0.0524 (12) | 0.0566 (13) | 0.0354 (10) | −0.0117 (10) | 0.0016 (9) | −0.0095 (9) |
C13 | 0.0700 (16) | 0.0784 (18) | 0.0613 (15) | −0.0032 (13) | 0.0036 (12) | −0.0339 (13) |
C14 | 0.0761 (18) | 0.102 (2) | 0.0401 (12) | −0.0310 (16) | 0.0055 (12) | 0.0008 (13) |
C15 | 0.0551 (12) | 0.0535 (12) | 0.0311 (9) | −0.0154 (10) | −0.0044 (9) | −0.0051 (9) |
C16 | 0.0558 (14) | 0.0591 (14) | 0.0654 (15) | −0.0112 (11) | 0.0032 (11) | −0.0067 (12) |
C17 | 0.0554 (16) | 0.103 (2) | 0.0771 (19) | −0.0049 (16) | 0.0058 (14) | −0.0050 (17) |
C18 | 0.0577 (17) | 0.157 (3) | 0.0544 (16) | −0.042 (2) | −0.0022 (13) | −0.0060 (19) |
C19 | 0.098 (2) | 0.117 (3) | 0.0534 (15) | −0.069 (2) | −0.0098 (15) | −0.0082 (16) |
C20 | 0.0793 (17) | 0.0670 (15) | 0.0489 (13) | −0.0319 (13) | −0.0067 (12) | −0.0120 (11) |
C21 | 0.0504 (12) | 0.0470 (11) | 0.0388 (10) | −0.0155 (9) | 0.0020 (9) | −0.0119 (9) |
C22 | 0.0437 (11) | 0.0493 (11) | 0.0413 (10) | −0.0137 (9) | 0.0005 (8) | −0.0115 (9) |
C23 | 0.0752 (17) | 0.0871 (19) | 0.0650 (15) | −0.0503 (15) | 0.0161 (13) | −0.0266 (14) |
C24 | 0.0499 (13) | 0.0900 (19) | 0.0539 (14) | 0.0001 (13) | −0.0072 (11) | −0.0137 (13) |
C25 | 0.0462 (11) | 0.0457 (11) | 0.0367 (10) | −0.0155 (9) | 0.0014 (8) | −0.0043 (8) |
C26 | 0.0748 (17) | 0.0596 (15) | 0.0525 (13) | −0.0027 (12) | −0.0076 (12) | −0.0080 (11) |
C27 | 0.085 (2) | 0.097 (2) | 0.0633 (17) | −0.0034 (18) | −0.0250 (15) | 0.0086 (16) |
C28 | 0.109 (3) | 0.114 (3) | 0.0461 (14) | −0.043 (2) | −0.0140 (15) | −0.0181 (16) |
C29 | 0.105 (2) | 0.0792 (19) | 0.0503 (14) | −0.0315 (17) | 0.0058 (15) | −0.0245 (14) |
C30 | 0.0676 (15) | 0.0556 (13) | 0.0439 (12) | −0.0137 (11) | 0.0042 (10) | −0.0117 (10) |
C31 | 0.0347 (10) | 0.0504 (12) | 0.0621 (13) | −0.0120 (9) | 0.0020 (9) | −0.0138 (10) |
C32 | 0.0571 (14) | 0.0621 (15) | 0.0674 (15) | −0.0162 (12) | 0.0167 (12) | −0.0246 (12) |
C33 | 0.0606 (15) | 0.0452 (13) | 0.096 (2) | −0.0101 (11) | 0.0197 (14) | −0.0254 (13) |
C34 | 0.0461 (12) | 0.0433 (12) | 0.0891 (19) | −0.0129 (10) | 0.0008 (12) | −0.0122 (12) |
C35 | 0.0544 (13) | 0.0588 (14) | 0.0634 (14) | −0.0060 (11) | −0.0084 (11) | −0.0155 (11) |
C36 | 0.0503 (13) | 0.0540 (13) | 0.0620 (14) | 0.0009 (10) | −0.0050 (11) | −0.0205 (11) |
C37 | 0.0652 (17) | 0.0453 (14) | 0.125 (3) | −0.0074 (13) | 0.0036 (17) | −0.0026 (15) |
C38 | 0.120 (3) | 0.087 (2) | 0.122 (3) | 0.011 (2) | −0.017 (3) | 0.019 (2) |
Sn1—O1 | 2.041 (2) | C17—C18 | 1.367 (5) |
Sn1—C11 | 2.144 (2) | C17—H17 | 0.9300 |
Sn1—C21 | 2.154 (2) | C18—C19 | 1.353 (5) |
Sn1—C1 | 2.157 (2) | C18—H18 | 0.9300 |
O1—C31 | 1.333 (3) | C19—C20 | 1.388 (4) |
O2—C37 | 1.203 (4) | C19—H19 | 0.9300 |
C1—C2 | 1.544 (3) | C20—H20 | 0.9300 |
C1—H1A | 0.9700 | C21—C22 | 1.547 (3) |
C1—H1B | 0.9700 | C21—H21A | 0.9700 |
C2—C3 | 1.527 (3) | C21—H21B | 0.9700 |
C2—C5 | 1.528 (3) | C22—C24 | 1.521 (3) |
C2—C4 | 1.544 (3) | C22—C25 | 1.530 (3) |
C3—H3A | 0.9600 | C22—C23 | 1.538 (3) |
C3—H3B | 0.9600 | C23—H23A | 0.9600 |
C3—H3C | 0.9600 | C23—H23B | 0.9600 |
C4—H4A | 0.9600 | C23—H23C | 0.9600 |
C4—H4B | 0.9600 | C24—H24A | 0.9600 |
C4—H4C | 0.9600 | C24—H24B | 0.9600 |
C5—C10 | 1.383 (3) | C24—H24C | 0.9600 |
C5—C6 | 1.390 (3) | C25—C26 | 1.376 (3) |
C6—C7 | 1.389 (4) | C25—C30 | 1.385 (3) |
C6—H6 | 0.9300 | C26—C27 | 1.397 (4) |
C7—C8 | 1.360 (5) | C26—H26 | 0.9300 |
C7—H7 | 0.9300 | C27—C28 | 1.354 (4) |
C8—C9 | 1.357 (4) | C27—H27 | 0.9300 |
C8—H8 | 0.9300 | C28—C29 | 1.358 (4) |
C9—C10 | 1.390 (3) | C28—H28 | 0.9300 |
C9—H9 | 0.9300 | C29—C30 | 1.372 (3) |
C10—H10 | 0.9300 | C29—H29 | 0.9300 |
C11—C12 | 1.539 (3) | C30—H30 | 0.9300 |
C11—H11A | 0.9700 | C31—C36 | 1.384 (3) |
C11—H11B | 0.9700 | C31—C32 | 1.399 (3) |
C12—C15 | 1.522 (3) | C32—C33 | 1.373 (3) |
C12—C13 | 1.535 (3) | C32—H32 | 0.9300 |
C12—C14 | 1.537 (3) | C33—C34 | 1.381 (4) |
C13—H13A | 0.9600 | C33—H33 | 0.9300 |
C13—H13B | 0.9600 | C34—C35 | 1.374 (3) |
C13—H13C | 0.9600 | C34—C37 | 1.490 (4) |
C14—H14A | 0.9600 | C35—C36 | 1.385 (3) |
C14—H14B | 0.9600 | C35—H35 | 0.9300 |
C14—H14C | 0.9600 | C36—H36 | 0.9300 |
C15—C16 | 1.382 (3) | C37—C38 | 1.500 (5) |
C15—C20 | 1.385 (3) | C38—H38A | 0.9600 |
C16—C17 | 1.376 (4) | C38—H38B | 0.9600 |
C16—H16 | 0.9300 | C38—H38C | 0.9600 |
O1—Sn1—C11 | 93.55 (7) | C18—C17—H17 | 119.9 |
O1—Sn1—C21 | 99.90 (7) | C16—C17—H17 | 119.9 |
C11—Sn1—C21 | 119.21 (8) | C19—C18—C17 | 119.1 (3) |
O1—Sn1—C1 | 109.00 (7) | C19—C18—H18 | 120.4 |
C11—Sn1—C1 | 115.07 (8) | C17—C18—H18 | 120.4 |
C21—Sn1—C1 | 115.49 (8) | C18—C19—C20 | 121.2 (3) |
C31—O1—Sn1 | 126.62 (13) | C18—C19—H19 | 119.4 |
C2—C1—Sn1 | 119.10 (14) | C20—C19—H19 | 119.4 |
C2—C1—H1A | 107.5 | C15—C20—C19 | 120.5 (3) |
Sn1—C1—H1A | 107.5 | C15—C20—H20 | 119.8 |
C2—C1—H1B | 107.5 | C19—C20—H20 | 119.8 |
Sn1—C1—H1B | 107.5 | C22—C21—Sn1 | 118.13 (13) |
H1A—C1—H1B | 107.0 | C22—C21—H21A | 107.8 |
C3—C2—C5 | 112.8 (2) | Sn1—C21—H21A | 107.8 |
C3—C2—C4 | 108.1 (2) | C22—C21—H21B | 107.8 |
C5—C2—C4 | 108.25 (19) | Sn1—C21—H21B | 107.8 |
C3—C2—C1 | 109.03 (19) | H21A—C21—H21B | 107.1 |
C5—C2—C1 | 110.00 (17) | C24—C22—C25 | 112.32 (18) |
C4—C2—C1 | 108.5 (2) | C24—C22—C23 | 108.2 (2) |
C2—C3—H3A | 109.5 | C25—C22—C23 | 108.86 (18) |
C2—C3—H3B | 109.5 | C24—C22—C21 | 109.37 (18) |
H3A—C3—H3B | 109.5 | C25—C22—C21 | 110.23 (16) |
C2—C3—H3C | 109.5 | C23—C22—C21 | 107.75 (17) |
H3A—C3—H3C | 109.5 | C22—C23—H23A | 109.5 |
H3B—C3—H3C | 109.5 | C22—C23—H23B | 109.5 |
C2—C4—H4A | 109.5 | H23A—C23—H23B | 109.5 |
C2—C4—H4B | 109.5 | C22—C23—H23C | 109.5 |
H4A—C4—H4B | 109.5 | H23A—C23—H23C | 109.5 |
C2—C4—H4C | 109.5 | H23B—C23—H23C | 109.5 |
H4A—C4—H4C | 109.5 | C22—C24—H24A | 109.5 |
H4B—C4—H4C | 109.5 | C22—C24—H24B | 109.5 |
C10—C5—C6 | 116.5 (2) | H24A—C24—H24B | 109.5 |
C10—C5—C2 | 120.1 (2) | C22—C24—H24C | 109.5 |
C6—C5—C2 | 123.3 (2) | H24A—C24—H24C | 109.5 |
C7—C6—C5 | 121.1 (3) | H24B—C24—H24C | 109.5 |
C7—C6—H6 | 119.5 | C26—C25—C30 | 116.7 (2) |
C5—C6—H6 | 119.5 | C26—C25—C22 | 120.58 (19) |
C8—C7—C6 | 121.3 (3) | C30—C25—C22 | 122.73 (19) |
C8—C7—H7 | 119.4 | C25—C26—C27 | 121.3 (3) |
C6—C7—H7 | 119.4 | C25—C26—H26 | 119.4 |
C9—C8—C7 | 118.5 (3) | C27—C26—H26 | 119.4 |
C9—C8—H8 | 120.7 | C28—C27—C26 | 120.0 (3) |
C7—C8—H8 | 120.7 | C28—C27—H27 | 120.0 |
C8—C9—C10 | 121.1 (3) | C26—C27—H27 | 120.0 |
C8—C9—H9 | 119.5 | C27—C28—C29 | 119.8 (3) |
C10—C9—H9 | 119.5 | C27—C28—H28 | 120.1 |
C5—C10—C9 | 121.4 (2) | C29—C28—H28 | 120.1 |
C5—C10—H10 | 119.3 | C28—C29—C30 | 120.3 (3) |
C9—C10—H10 | 119.3 | C28—C29—H29 | 119.9 |
C12—C11—Sn1 | 118.51 (14) | C30—C29—H29 | 119.9 |
C12—C11—H11A | 107.7 | C29—C30—C25 | 121.9 (2) |
Sn1—C11—H11A | 107.7 | C29—C30—H30 | 119.0 |
C12—C11—H11B | 107.7 | C25—C30—H30 | 119.0 |
Sn1—C11—H11B | 107.7 | O1—C31—C36 | 123.31 (19) |
H11A—C11—H11B | 107.1 | O1—C31—C32 | 119.3 (2) |
C15—C12—C13 | 112.7 (2) | C36—C31—C32 | 117.4 (2) |
C15—C12—C14 | 108.08 (18) | C33—C32—C31 | 120.7 (2) |
C13—C12—C14 | 108.4 (2) | C33—C32—H32 | 119.7 |
C15—C12—C11 | 110.59 (17) | C31—C32—H32 | 119.7 |
C13—C12—C11 | 108.87 (18) | C32—C33—C34 | 121.7 (2) |
C14—C12—C11 | 108.05 (19) | C32—C33—H33 | 119.1 |
C12—C13—H13A | 109.5 | C34—C33—H33 | 119.1 |
C12—C13—H13B | 109.5 | C35—C34—C33 | 117.8 (2) |
H13A—C13—H13B | 109.5 | C35—C34—C37 | 122.6 (3) |
C12—C13—H13C | 109.5 | C33—C34—C37 | 119.6 (2) |
H13A—C13—H13C | 109.5 | C34—C35—C36 | 121.2 (2) |
H13B—C13—H13C | 109.5 | C34—C35—H35 | 119.4 |
C12—C14—H14A | 109.5 | C36—C35—H35 | 119.4 |
C12—C14—H14B | 109.5 | C31—C36—C35 | 121.1 (2) |
H14A—C14—H14B | 109.5 | C31—C36—H36 | 119.4 |
C12—C14—H14C | 109.5 | C35—C36—H36 | 119.4 |
H14A—C14—H14C | 109.5 | O2—C37—C34 | 120.2 (3) |
H14B—C14—H14C | 109.5 | O2—C37—C38 | 120.9 (3) |
C16—C15—C20 | 117.1 (2) | C34—C37—C38 | 118.9 (3) |
C16—C15—C12 | 119.9 (2) | C37—C38—H38A | 109.5 |
C20—C15—C12 | 123.0 (2) | C37—C38—H38B | 109.5 |
C17—C16—C15 | 121.8 (3) | H38A—C38—H38B | 109.5 |
C17—C16—H16 | 119.1 | C37—C38—H38C | 109.5 |
C15—C16—H16 | 119.1 | H38A—C38—H38C | 109.5 |
C18—C17—C16 | 120.3 (3) | H38B—C38—H38C | 109.5 |
C11—Sn1—O1—C31 | −163.81 (17) | C16—C15—C20—C19 | −1.3 (3) |
C21—Sn1—O1—C31 | −43.34 (18) | C12—C15—C20—C19 | −179.1 (2) |
C1—Sn1—O1—C31 | 78.13 (18) | C18—C19—C20—C15 | 1.2 (4) |
O1—Sn1—C1—C2 | 67.67 (17) | O1—Sn1—C21—C22 | 144.23 (15) |
C11—Sn1—C1—C2 | −35.82 (19) | C11—Sn1—C21—C22 | −116.01 (15) |
C21—Sn1—C1—C2 | 179.11 (15) | C1—Sn1—C21—C22 | 27.53 (18) |
Sn1—C1—C2—C3 | −68.2 (2) | Sn1—C21—C22—C24 | 59.0 (2) |
Sn1—C1—C2—C5 | 56.0 (2) | Sn1—C21—C22—C25 | −64.9 (2) |
Sn1—C1—C2—C4 | 174.23 (16) | Sn1—C21—C22—C23 | 176.41 (15) |
C3—C2—C5—C10 | 174.1 (2) | C24—C22—C25—C26 | −179.1 (2) |
C4—C2—C5—C10 | −66.3 (3) | C23—C22—C25—C26 | 61.1 (3) |
C1—C2—C5—C10 | 52.1 (3) | C21—C22—C25—C26 | −56.9 (3) |
C3—C2—C5—C6 | −4.1 (3) | C24—C22—C25—C30 | 0.9 (3) |
C4—C2—C5—C6 | 115.6 (3) | C23—C22—C25—C30 | −118.9 (2) |
C1—C2—C5—C6 | −126.1 (2) | C21—C22—C25—C30 | 123.1 (2) |
C10—C5—C6—C7 | −1.8 (4) | C30—C25—C26—C27 | −0.2 (4) |
C2—C5—C6—C7 | 176.4 (2) | C22—C25—C26—C27 | 179.7 (2) |
C5—C6—C7—C8 | 0.4 (5) | C25—C26—C27—C28 | −0.2 (5) |
C6—C7—C8—C9 | 1.7 (5) | C26—C27—C28—C29 | 0.5 (5) |
C7—C8—C9—C10 | −2.4 (4) | C27—C28—C29—C30 | −0.4 (5) |
C6—C5—C10—C9 | 1.1 (3) | C28—C29—C30—C25 | −0.1 (4) |
C2—C5—C10—C9 | −177.1 (2) | C26—C25—C30—C29 | 0.4 (4) |
C8—C9—C10—C5 | 1.0 (4) | C22—C25—C30—C29 | −179.6 (2) |
O1—Sn1—C11—C12 | 90.31 (16) | Sn1—O1—C31—C36 | −37.9 (3) |
C21—Sn1—C11—C12 | −13.1 (2) | Sn1—O1—C31—C32 | 143.00 (17) |
C1—Sn1—C11—C12 | −156.78 (15) | O1—C31—C32—C33 | 177.8 (2) |
Sn1—C11—C12—C15 | 66.0 (2) | C36—C31—C32—C33 | −1.4 (3) |
Sn1—C11—C12—C13 | −58.4 (2) | C31—C32—C33—C34 | 0.9 (4) |
Sn1—C11—C12—C14 | −175.93 (16) | C32—C33—C34—C35 | 0.8 (4) |
C13—C12—C15—C16 | 174.6 (2) | C32—C33—C34—C37 | −177.0 (2) |
C14—C12—C15—C16 | −65.6 (3) | C33—C34—C35—C36 | −1.9 (4) |
C11—C12—C15—C16 | 52.5 (3) | C37—C34—C35—C36 | 175.8 (2) |
C13—C12—C15—C20 | −7.6 (3) | O1—C31—C36—C35 | −178.9 (2) |
C14—C12—C15—C20 | 112.2 (2) | C32—C31—C36—C35 | 0.3 (3) |
C11—C12—C15—C20 | −129.7 (2) | C34—C35—C36—C31 | 1.4 (4) |
C20—C15—C16—C17 | 0.9 (3) | C35—C34—C37—O2 | −167.0 (3) |
C12—C15—C16—C17 | 178.8 (2) | C33—C34—C37—O2 | 10.7 (4) |
C15—C16—C17—C18 | −0.4 (4) | C35—C34—C37—C38 | 13.0 (4) |
C16—C17—C18—C19 | 0.2 (4) | C33—C34—C37—C38 | −169.3 (3) |
C17—C18—C19—C20 | −0.6 (4) |
Experimental details
Crystal data | |
Chemical formula | [Sn(C10H13)3(C8H7O2)] |
Mr | 653.44 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 9.5062 (7), 9.7309 (7), 19.0769 (15) |
α, β, γ (°) | 78.704 (2), 87.906 (1), 76.874 (1) |
V (Å3) | 1685.2 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.79 |
Crystal size (mm) | 0.41 × 0.30 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.738, 0.846 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13220, 6532, 6022 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.026, 0.067, 1.03 |
No. of reflections | 6532 |
No. of parameters | 371 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.29 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
Sn1—O1 | 2.041 (2) | Sn1—C21 | 2.154 (2) |
Sn1—C11 | 2.144 (2) | Sn1—C1 | 2.157 (2) |
O1—Sn1—C11 | 93.55 (7) | O1—Sn1—C1 | 109.00 (7) |
O1—Sn1—C21 | 99.90 (7) | C11—Sn1—C1 | 115.07 (8) |
C11—Sn1—C21 | 119.21 (8) | C21—Sn1—C1 | 115.49 (8) |
Little attention has been paid to the condensation reaction of tris(2-methyl-2-phenylpropyl)tin oxide, {[C6H5C(CH3)2CH2]3Sn}2O, an industrial miticide, with phenols in the literature. In two reported structures, tris(2-methyl-2-phenylpropyl)tin pentachlorophenoate (Zhang et al., 2002) and tris(2-methyl-2-phenylpropyl)tin 4-nitrophenolate (Yang et al., 2006), the tin atom is four coordinated.
In the title compound, (I), the Sn atom is also four-coordinate and possess a distorted SnOC3 tetrahedral geometry (Fig. 1 & Table 1). This is different from Me3SnOMe, in which almost planar trimethyltin groups are linked by two methoxy ligands forming infinite one-dimensional zigzag chains with nearly ideally trigonal-bipyramidal coordinated tin atom (Domingos & Sheldrick, 1974), due to the crowding of the four bulky groups at the Sn atom in (I). The Sn—C distances lie in the narrow range of 2.144 (2)–2.157 (2) Å, in agreement with those [2.142 (2)–2.158 (2) Å] in tris(2-methyl-2-phenylpropyl)tin 4-nitrophenolate (Yang et al., 2006), but slightly longer than those [2.105 (4)–2.114 (4) Å] in tris(2-methyl-2-phenylpropyl)tin pentachlorophenoate (Zhang et al., 2002). The Sn—O separation in (I) of 2.045 (2) Å is almost same as that of tris(2-methyl-2-phenylpropyl)tin 4-nitrophenolate and shorter than that [2.103 (3) Å] found in tris(2-methyl-2-phenylpropyl)tin pentachlorophenoate.