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The silole ring of the title compound, C22H46OSi3, is planar. Geometric parameters do not show unusual values. The H atom and the hydr­oxy group on the silole Si atom are mutually disordered.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007112/kp2004sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007112/kp2004Isup2.hkl
Contains datablock I

CCDC reference: 605247

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • H-atom completeness 98%
  • Disorder in main residue
  • R factor = 0.053
  • wR factor = 0.147
  • Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT420_ALERT_2_C D-H Without Acceptor Si2 - >H2 ... ?
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C22 H46 O1 Si3 Atom count from the _atom_site data: C22 H45 O1 Si3 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 2 From the CIF: _chemical_formula_sum C22 H46 O Si3 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 44.00 44.00 0.00 H 92.00 90.00 2.00 O 2.00 2.00 0.00 Si 6.00 6.00 0.00
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 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

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PLATON.

1-Hydroxy-2,5-bis(triisopropylsilyl)silole top
Crystal data top
C22H46OSi3Z = 2
Mr = 410.86F(000) = 456
Triclinic, P1Dx = 1.047 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8597 (8) ÅCell parameters from 13100 reflections
b = 13.5714 (14) Åθ = 3.5–25.7°
c = 13.6482 (14) ŵ = 0.19 mm1
α = 110.596 (8)°T = 173 K
β = 98.999 (9)°Rod, colourless
γ = 100.074 (8)°0.40 × 0.20 × 0.10 mm
V = 1303.7 (3) Å3
Data collection top
Stoe IPDS-II two-circle
diffractometer
4844 independent reflections
Radiation source: fine-focus sealed tube4178 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
ω scansθmax = 25.7°, θmin = 3.5°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 99
Tmin = 0.928, Tmax = 0.971k = 1614
13100 measured reflectionsl = 1616
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.083P)2 + 0.5074P]
where P = (Fo2 + 2Fc2)/3
4844 reflections(Δ/σ)max = 0.001
245 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.52 e Å3
Special details top

Experimental. ;

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*/UeqOcc. (<1)
C10.6733 (3)0.59945 (16)0.31688 (17)0.0266 (4)
Si20.64001 (11)0.49159 (6)0.17915 (5)0.0422 (2)
H20.45800.44080.14780.051*0.537 (5)
H2'0.75890.53610.13050.051*0.463 (5)
O20.6797 (6)0.5176 (3)0.0822 (3)0.0579 (14)0.537 (5)
O2'0.4635 (6)0.4464 (4)0.0952 (3)0.0624 (16)0.463 (5)
C30.7491 (3)0.39766 (16)0.22434 (16)0.0260 (4)
C40.7979 (3)0.45076 (18)0.33284 (17)0.0328 (5)
H40.85680.42010.37670.039*
C50.7571 (3)0.55841 (18)0.38208 (17)0.0340 (5)
H50.78940.59740.45800.041*
Si10.61149 (7)0.73275 (4)0.36416 (4)0.02483 (17)
C110.7567 (3)0.82096 (17)0.50385 (17)0.0312 (5)
H110.74030.77680.54840.037*
C120.9567 (3)0.8478 (2)0.5088 (2)0.0433 (6)
H12A0.99170.78060.47310.065*
H12B1.02350.88250.58420.065*
H12C0.98260.89730.47230.065*
C130.6977 (4)0.92563 (19)0.5603 (2)0.0418 (6)
H13A0.57010.90690.55670.063*
H13B0.72200.97550.52400.063*
H13C0.76390.96070.63580.063*
C140.3698 (3)0.70783 (19)0.37415 (19)0.0350 (5)
H140.34230.78040.40310.042*
C150.3393 (4)0.6530 (2)0.4536 (2)0.0487 (7)
H15A0.42340.69580.52330.073*
H15B0.35770.57960.42520.073*
H15C0.21740.64880.46280.073*
C160.2395 (3)0.6416 (3)0.2646 (2)0.0503 (7)
H16A0.25930.67730.21480.076*
H16B0.11720.63680.27330.076*
H16C0.25840.56830.23570.076*
C170.6332 (3)0.79217 (18)0.25826 (18)0.0324 (5)
H170.55270.73660.18940.039*
C180.8194 (4)0.8111 (2)0.2356 (2)0.0466 (6)
H18A0.86170.74480.22230.070*
H18B0.90170.87090.29800.070*
H18C0.81340.82950.17210.070*
C190.5666 (4)0.8962 (2)0.2788 (2)0.0477 (6)
H19A0.44760.88400.29260.072*
H19B0.56160.91480.21540.072*
H19C0.64820.95610.34150.072*
Si30.78787 (7)0.26182 (4)0.14893 (4)0.02380 (16)
C310.9736 (3)0.23841 (18)0.23855 (18)0.0313 (5)
H310.93700.24830.30770.038*
C321.1531 (3)0.3219 (2)0.2685 (2)0.0424 (6)
H32A1.13570.39550.29700.064*
H32B1.20060.31100.20430.064*
H32C1.23710.31210.32340.064*
C330.9976 (4)0.1211 (2)0.1934 (2)0.0439 (6)
H33A0.88250.06910.17480.066*
H33B1.08120.11070.24800.066*
H33C1.04440.10940.12880.066*
C340.5781 (3)0.15260 (16)0.12166 (18)0.0293 (5)
H340.60370.08060.08520.035*
C350.5298 (3)0.1545 (2)0.2273 (2)0.0386 (5)
H35A0.63230.14950.27480.058*
H35B0.42920.09270.21130.058*
H35C0.49710.22240.26310.058*
C360.4197 (3)0.1606 (2)0.0454 (2)0.0374 (5)
H36A0.45280.15870.02140.056*
H36B0.38720.22880.08020.056*
H36C0.31810.09920.02880.056*
C370.8304 (3)0.25987 (18)0.01488 (17)0.0313 (5)
H370.72320.27530.02120.038*
C380.8412 (4)0.1474 (2)0.0627 (2)0.0466 (6)
H38A0.73840.09160.06810.070*
H38B0.95090.13090.03500.070*
H38C0.84140.14840.13410.070*
C390.9895 (3)0.3487 (2)0.0234 (2)0.0438 (6)
H39A0.98080.41950.07250.066*
H39B0.98890.35000.04800.066*
H39C1.10020.33330.05120.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0285 (10)0.0220 (10)0.0303 (10)0.0113 (8)0.0083 (8)0.0083 (8)
Si20.0648 (5)0.0324 (4)0.0283 (3)0.0319 (3)0.0001 (3)0.0059 (3)
O20.101 (3)0.057 (2)0.0270 (17)0.047 (2)0.0096 (18)0.0191 (16)
O2'0.067 (3)0.055 (3)0.045 (2)0.031 (2)0.020 (2)0.001 (2)
C30.0263 (10)0.0226 (10)0.0298 (10)0.0098 (8)0.0068 (8)0.0092 (8)
C40.0473 (13)0.0268 (11)0.0299 (11)0.0227 (10)0.0078 (9)0.0117 (9)
C50.0515 (14)0.0261 (11)0.0258 (10)0.0210 (10)0.0091 (9)0.0064 (9)
Si10.0276 (3)0.0197 (3)0.0291 (3)0.0126 (2)0.0085 (2)0.0079 (2)
C110.0373 (12)0.0242 (11)0.0329 (11)0.0136 (9)0.0087 (9)0.0091 (9)
C120.0374 (13)0.0362 (13)0.0460 (14)0.0083 (10)0.0039 (11)0.0068 (11)
C130.0520 (15)0.0291 (12)0.0371 (13)0.0182 (11)0.0073 (11)0.0021 (10)
C140.0308 (11)0.0327 (12)0.0430 (13)0.0149 (9)0.0142 (10)0.0108 (10)
C150.0424 (14)0.0570 (17)0.0466 (15)0.0077 (12)0.0184 (12)0.0189 (13)
C160.0311 (13)0.0601 (18)0.0563 (16)0.0132 (12)0.0050 (11)0.0199 (14)
C170.0413 (12)0.0261 (11)0.0343 (11)0.0181 (9)0.0116 (9)0.0113 (9)
C180.0504 (15)0.0488 (15)0.0567 (16)0.0202 (12)0.0254 (13)0.0305 (13)
C190.0721 (18)0.0395 (14)0.0474 (14)0.0347 (13)0.0200 (13)0.0233 (12)
Si30.0248 (3)0.0205 (3)0.0267 (3)0.0123 (2)0.0073 (2)0.0063 (2)
C310.0338 (11)0.0292 (11)0.0349 (11)0.0181 (9)0.0089 (9)0.0120 (9)
C320.0318 (12)0.0456 (14)0.0494 (14)0.0153 (11)0.0018 (10)0.0187 (12)
C330.0502 (15)0.0363 (13)0.0502 (15)0.0294 (12)0.0085 (12)0.0154 (11)
C340.0289 (10)0.0191 (10)0.0375 (11)0.0109 (8)0.0096 (9)0.0051 (9)
C350.0372 (12)0.0343 (12)0.0480 (14)0.0098 (10)0.0146 (11)0.0182 (11)
C360.0288 (11)0.0368 (13)0.0409 (12)0.0093 (10)0.0068 (9)0.0084 (10)
C370.0298 (11)0.0340 (12)0.0304 (11)0.0140 (9)0.0088 (9)0.0092 (9)
C380.0541 (15)0.0450 (15)0.0357 (13)0.0199 (12)0.0177 (11)0.0032 (11)
C390.0422 (14)0.0505 (15)0.0387 (13)0.0085 (12)0.0137 (11)0.0173 (12)
Geometric parameters (Å, º) top
C1—C51.353 (3)C18—H18A0.9800
C1—Si11.873 (2)C18—H18B0.9800
C1—Si21.877 (2)C18—H18C0.9800
Si2—O2'1.525 (4)C19—H19A0.9800
Si2—O21.546 (3)C19—H19B0.9800
Si2—C31.874 (2)C19—H19C0.9800
Si2—H21.4000Si3—C311.899 (2)
Si2—H2'1.4001Si3—C341.902 (2)
C3—C41.354 (3)Si3—C371.903 (2)
C3—Si31.873 (2)C31—C321.541 (3)
C4—C51.493 (3)C31—C331.549 (3)
C4—H40.9500C31—H311.0000
C5—H50.9500C32—H32A0.9800
Si1—C111.899 (2)C32—H32B0.9800
Si1—C171.902 (2)C32—H32C0.9800
Si1—C141.905 (2)C33—H33A0.9800
C11—C121.535 (3)C33—H33B0.9800
C11—C131.548 (3)C33—H33C0.9800
C11—H111.0000C34—C361.538 (3)
C12—H12A0.9800C34—C351.541 (3)
C12—H12B0.9800C34—H341.0000
C12—H12C0.9800C35—H35A0.9800
C13—H13A0.9800C35—H35B0.9800
C13—H13B0.9800C35—H35C0.9800
C13—H13C0.9800C36—H36A0.9800
C14—C161.531 (4)C36—H36B0.9800
C14—C151.540 (3)C36—H36C0.9800
C14—H141.0000C37—C391.536 (3)
C15—H15A0.9800C37—C381.547 (3)
C15—H15B0.9800C37—H371.0000
C15—H15C0.9800C38—H38A0.9800
C16—H16A0.9800C38—H38B0.9800
C16—H16B0.9800C38—H38C0.9800
C16—H16C0.9800C39—H39A0.9800
C17—C181.540 (3)C39—H39B0.9800
C17—C191.540 (3)C39—H39C0.9800
C17—H171.0000
C5—C1—Si1124.84 (16)Si1—C17—H17105.8
C5—C1—Si2102.90 (14)C17—C18—H18A109.5
Si1—C1—Si2132.26 (12)C17—C18—H18B109.5
O2'—Si2—O275.0 (3)H18A—C18—H18B109.5
O2'—Si2—C3119.94 (19)C17—C18—H18C109.5
O2—Si2—C3121.28 (15)H18A—C18—H18C109.5
O2'—Si2—C1123.53 (19)H18B—C18—H18C109.5
O2—Si2—C1122.86 (16)C17—C19—H19A109.5
C3—Si2—C196.46 (9)C17—C19—H19B109.5
O2—Si2—H2104.5H19A—C19—H19B109.5
C3—Si2—H2104.9C17—C19—H19C109.5
C1—Si2—H2104.9H19A—C19—H19C109.5
O2'—Si2—H2'104.5H19B—C19—H19C109.5
C3—Si2—H2'105.3C3—Si3—C31108.25 (10)
C1—Si2—H2'105.3C3—Si3—C34108.57 (9)
H2—Si2—H2'134.0C31—Si3—C34107.87 (10)
Si2—O2—H2'64.6C3—Si3—C37107.76 (10)
Si2—O2'—H266.0C31—Si3—C37115.50 (10)
C4—C3—Si2103.03 (15)C34—Si3—C37108.72 (10)
C4—C3—Si3124.54 (16)C32—C31—C33110.48 (19)
Si2—C3—Si3132.42 (12)C32—C31—Si3113.88 (16)
C3—C4—C5118.68 (19)C33—C31—Si3113.33 (16)
C3—C4—H4120.7C32—C31—H31106.2
C5—C4—H4120.7C33—C31—H31106.2
C1—C5—C4118.92 (19)Si3—C31—H31106.2
C1—C5—H5120.5C31—C32—H32A109.5
C4—C5—H5120.5C31—C32—H32B109.5
C1—Si1—C11108.47 (10)H32A—C32—H32B109.5
C1—Si1—C17107.44 (9)C31—C32—H32C109.5
C11—Si1—C17114.84 (10)H32A—C32—H32C109.5
C1—Si1—C14109.02 (10)H32B—C32—H32C109.5
C11—Si1—C14108.30 (10)C31—C33—H33A109.5
C17—Si1—C14108.65 (11)C31—C33—H33B109.5
C12—C11—C13110.61 (19)H33A—C33—H33B109.5
C12—C11—Si1114.38 (15)C31—C33—H33C109.5
C13—C11—Si1113.59 (16)H33A—C33—H33C109.5
C12—C11—H11105.8H33B—C33—H33C109.5
C13—C11—H11105.8C36—C34—C35110.73 (18)
Si1—C11—H11105.8C36—C34—Si3112.48 (15)
C11—C12—H12A109.5C35—C34—Si3111.32 (15)
C11—C12—H12B109.5C36—C34—H34107.3
H12A—C12—H12B109.5C35—C34—H34107.3
C11—C12—H12C109.5Si3—C34—H34107.3
H12A—C12—H12C109.5C34—C35—H35A109.5
H12B—C12—H12C109.5C34—C35—H35B109.5
C11—C13—H13A109.5H35A—C35—H35B109.5
C11—C13—H13B109.5C34—C35—H35C109.5
H13A—C13—H13B109.5H35A—C35—H35C109.5
C11—C13—H13C109.5H35B—C35—H35C109.5
H13A—C13—H13C109.5C34—C36—H36A109.5
H13B—C13—H13C109.5C34—C36—H36B109.5
C16—C14—C15110.0 (2)H36A—C36—H36B109.5
C16—C14—Si1112.77 (16)C34—C36—H36C109.5
C15—C14—Si1111.70 (17)H36A—C36—H36C109.5
C16—C14—H14107.3H36B—C36—H36C109.5
C15—C14—H14107.3C39—C37—C38110.28 (19)
Si1—C14—H14107.3C39—C37—Si3115.04 (16)
C14—C15—H15A109.5C38—C37—Si3113.69 (17)
C14—C15—H15B109.5C39—C37—H37105.6
H15A—C15—H15B109.5C38—C37—H37105.6
C14—C15—H15C109.5Si3—C37—H37105.6
H15A—C15—H15C109.5C37—C38—H38A109.5
H15B—C15—H15C109.5C37—C38—H38B109.5
C14—C16—H16A109.5H38A—C38—H38B109.5
C14—C16—H16B109.5C37—C38—H38C109.5
H16A—C16—H16B109.5H38A—C38—H38C109.5
C14—C16—H16C109.5H38B—C38—H38C109.5
H16A—C16—H16C109.5C37—C39—H39A109.5
H16B—C16—H16C109.5C37—C39—H39B109.5
C18—C17—C19109.5 (2)H39A—C39—H39B109.5
C18—C17—Si1115.19 (17)C37—C39—H39C109.5
C19—C17—Si1113.95 (15)H39A—C39—H39C109.5
C18—C17—H17105.8H39B—C39—H39C109.5
C19—C17—H17105.8
C5—C1—Si2—O2'132.1 (3)C11—Si1—C14—C1558.15 (19)
Si1—C1—Si2—O2'47.3 (3)C17—Si1—C14—C15176.49 (16)
C5—C1—Si2—O2134.6 (2)C1—Si1—C17—C1858.8 (2)
Si1—C1—Si2—O246.0 (3)C11—Si1—C17—C1861.9 (2)
C5—C1—Si2—C30.56 (17)C14—Si1—C17—C18176.64 (17)
Si1—C1—Si2—C3179.98 (15)C1—Si1—C17—C19173.46 (18)
O2'—Si2—C3—C4134.5 (3)C11—Si1—C17—C1965.8 (2)
O2—Si2—C3—C4135.5 (2)C14—Si1—C17—C1955.6 (2)
C1—Si2—C3—C40.49 (16)C4—C3—Si3—C3120.9 (2)
O2'—Si2—C3—Si344.6 (3)Si2—C3—Si3—C31160.11 (14)
O2—Si2—C3—Si345.3 (3)C4—C3—Si3—C3495.9 (2)
C1—Si2—C3—Si3179.62 (15)Si2—C3—Si3—C3483.05 (16)
Si2—C3—C4—C50.3 (3)C4—C3—Si3—C37146.49 (19)
Si3—C3—C4—C5179.52 (16)Si2—C3—Si3—C3734.54 (18)
Si1—C1—C5—C4179.97 (16)C3—Si3—C31—C3262.22 (18)
Si2—C1—C5—C40.5 (3)C34—Si3—C31—C32179.52 (15)
C3—C4—C5—C10.1 (3)C37—Si3—C31—C3258.65 (19)
C5—C1—Si1—C1121.3 (2)C3—Si3—C31—C33170.36 (16)
Si2—C1—Si1—C11159.40 (14)C34—Si3—C31—C3353.06 (18)
C5—C1—Si1—C17146.0 (2)C37—Si3—C31—C3368.77 (19)
Si2—C1—Si1—C1734.71 (18)C3—Si3—C34—C3665.36 (17)
C5—C1—Si1—C1496.4 (2)C31—Si3—C34—C36177.55 (14)
Si2—C1—Si1—C1482.87 (17)C37—Si3—C34—C3651.61 (17)
C1—Si1—C11—C1261.57 (19)C3—Si3—C34—C3559.58 (17)
C17—Si1—C11—C1258.62 (19)C31—Si3—C34—C3557.50 (17)
C14—Si1—C11—C12179.76 (17)C37—Si3—C34—C35176.56 (15)
C1—Si1—C11—C13170.14 (16)C3—Si3—C37—C3958.79 (19)
C17—Si1—C11—C1369.67 (19)C31—Si3—C37—C3962.3 (2)
C14—Si1—C11—C1351.95 (19)C34—Si3—C37—C39176.29 (16)
C1—Si1—C14—C1664.9 (2)C3—Si3—C37—C38172.70 (17)
C11—Si1—C14—C16177.30 (18)C31—Si3—C37—C3866.2 (2)
C17—Si1—C14—C1651.9 (2)C34—Si3—C37—C3855.20 (19)
C1—Si1—C14—C1559.69 (19)
 

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