tert-Butoxy-triphenyl-silane.

The title compound, C(22)H(24)OSi or Ph(3)SiO(t)Bu, shows a distorted tetra-hedral coordination sphere around the Si atom. The C-O-Si angle is 135.97 (12)° and the O-Si distance is 1.6244 (13) Å. The mol-ecules are held together by weak inter-actions only. An H⋯H distance of 2.2924 (7) Å is found between aryl H atoms and is the shortest inter-molecular distance in the structure. With regard to the broad applicability of R(3)SiO structural motifs in all fields of chemistry, the mol-ecule demonstrates a common model system for silicon centers surrounded by sterically demanding substituents.

Related literature

For the synthesis of Ph3SiO-t-Bu, see: Gilman et al. (1953 ▶). For the synthesis and structure of Ph3SiO-i-Pr, see: Wojtczak et al. (1996 ▶). For selected transition-metal complexes containing Ph3SiO groups, see: Bindl et al. (2009 ▶); Johnson et al. (2000 ▶); Ruiz et al. (2004 ▶); Schweder et al. (1999 ▶); Schweder et al. (2006 ▶); Wolff von Gudenberg et al. (1994 ▶). For selected main-group compounds containing Ph3SiO units, see: Apblett & Barron (1993 ▶); Chen et al. (2008 ▶); Ferguson et al. (1996 ▶, 2005 ▶). For applications of silyl ethers in protecting group chemistry, see: Scheidt et al. (2002 ▶); Vintonyak & Maier (2007 ▶). For comparative O—Si distances, see: Bowes et al. (2002 ▶); Wojtczak et al. (1996 ▶) and for C—Si distances, see: Dilman et al. (2004 ▶); Lee et al. (2001 ▶); Wojtczak et al. (1996 ▶).

Experimental

Crystal data

C22H24OSi

M = 332.5

Monoclinic,

a = 9.8054 (12) Å

b = 20.201 (7) Å

c = 10.231 (2) Å

β = 111.311 (18)°

V = 1888.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 173 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur S diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.962, T max = 0.975

23180 measured reflections

4203 independent reflections

2597 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.100

S = 0.89

4203 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002722/fb2173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002722/fb2173Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H24OSi	F(000) = 712
Mr = 332.5	Dx = 1.170 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6858 reflections
a = 9.8054 (12) Å	θ = 2.2–29.1°
b = 20.201 (7) Å	µ = 0.13 mm−1
c = 10.231 (2) Å	T = 173 K
β = 111.311 (18)°	Block, colourless
V = 1888.0 (8) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur S diffractometer	4203 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2597 reflections with I > 2σ(I)
graphite	Rint = 0.045
ω scans	θmax = 27.2°, θmin = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	h = −12→12
Tmin = 0.962, Tmax = 0.975	k = −26→25
23180 measured reflections	l = −13→13

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)] = 0.042	Hydrogen site location: difference Fourier map
wR(F2) = 0.100	H-atom parameters constrained
S = 0.89	w = 1/[σ2(Fo2) + (0.0535P)2] where P = (Fo2 + 2Fc2)/3
4203 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm

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
C1	0.27284 (19)	0.12279 (9)	0.61661 (17)	0.0278 (4)
C2	0.1958 (2)	0.08722 (10)	0.68339 (19)	0.0403 (5)
H2	0.0935	0.0808	0.637	0.048*
C3	0.2644 (3)	0.06106 (11)	0.8152 (2)	0.0556 (6)
H3	0.2098	0.0363	0.8583	0.067*
C4	0.4122 (3)	0.07079 (12)	0.8846 (2)	0.0615 (7)
H4	0.4593	0.0535	0.9764	0.074*
C5	0.4911 (3)	0.10533 (11)	0.8215 (2)	0.0506 (6)
H5	0.5932	0.1119	0.8692	0.061*
C6	0.4227 (2)	0.13062 (9)	0.68881 (19)	0.0358 (5)
H6	0.4789	0.154	0.6454	0.043*
C7	0.27111 (17)	0.23135 (8)	0.41104 (17)	0.0238 (4)
C8	0.27112 (18)	0.24872 (9)	0.27948 (18)	0.0285 (4)
H8	0.223	0.2207	0.2017	0.034*
C9	0.3389 (2)	0.30526 (9)	0.25882 (19)	0.0331 (4)
H9	0.3368	0.3162	0.1678	0.04*
C10	0.40953 (19)	0.34582 (9)	0.3708 (2)	0.0349 (4)
H10	0.4588	0.3843	0.3576	0.042*
C11	0.40926 (19)	0.33105 (9)	0.50166 (19)	0.0337 (5)
H11	0.4562	0.3598	0.5784	0.04*
C12	0.34073 (19)	0.27453 (9)	0.52133 (18)	0.0292 (4)
H12	0.3409	0.2647	0.6122	0.035*
C13	−0.01766 (18)	0.17492 (9)	0.40683 (17)	0.0262 (4)
C14	−0.1271 (2)	0.12846 (10)	0.3473 (2)	0.0400 (5)
H14	−0.101	0.0856	0.3261	0.048*
C15	−0.2717 (2)	0.14281 (12)	0.3185 (2)	0.0533 (6)
H15	−0.3444	0.1101	0.2776	0.064*
C16	−0.3119 (2)	0.20462 (12)	0.3486 (2)	0.0504 (6)
H16	−0.4121	0.2147	0.3288	0.061*
C17	−0.2070 (2)	0.25123 (10)	0.4069 (2)	0.0425 (5)
H17	−0.2342	0.294	0.4272	0.051*
C18	−0.0612 (2)	0.23652 (9)	0.43663 (18)	0.0315 (4)
H18	0.0108	0.2694	0.4784	0.038*
C19	0.2491 (2)	0.04775 (9)	0.29651 (19)	0.0333 (4)
C20	0.2387 (2)	−0.01047 (10)	0.3858 (2)	0.0500 (6)
H20A	0.2889	0.0004	0.4852	0.075*
H20B	0.285	−0.0493	0.3621	0.075*
H20C	0.1356	−0.0201	0.3679	0.075*
C21	0.1796 (3)	0.02943 (11)	0.1418 (2)	0.0527 (6)
H21A	0.0764	0.018	0.1196	0.079*
H21B	0.2311	−0.0086	0.1223	0.079*
H21C	0.1864	0.0671	0.0842	0.079*
C22	0.4025 (2)	0.06981 (12)	0.3291 (3)	0.0613 (7)
H22A	0.404	0.1062	0.2664	0.092*
H22B	0.4607	0.0328	0.3159	0.092*
H22C	0.4439	0.085	0.4267	0.092*
O	0.16116 (12)	0.10112 (6)	0.31536 (11)	0.0266 (3)
Si	0.17626 (5)	0.15575 (2)	0.43643 (5)	0.02347 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0329 (10)	0.0245 (10)	0.0250 (9)	0.0035 (8)	0.0092 (8)	−0.0018 (8)
C2	0.0516 (13)	0.0398 (12)	0.0318 (11)	0.0006 (10)	0.0180 (10)	0.0021 (9)
C3	0.094 (2)	0.0419 (14)	0.0394 (13)	0.0094 (13)	0.0348 (14)	0.0088 (11)
C4	0.098 (2)	0.0445 (15)	0.0280 (12)	0.0286 (14)	0.0059 (13)	0.0077 (11)
C5	0.0549 (14)	0.0406 (13)	0.0373 (12)	0.0218 (11)	−0.0060 (11)	−0.0078 (10)
C6	0.0378 (11)	0.0305 (11)	0.0320 (11)	0.0081 (9)	0.0042 (9)	−0.0047 (9)
C7	0.0190 (8)	0.0253 (9)	0.0261 (10)	0.0020 (7)	0.0069 (7)	0.0019 (8)
C8	0.0297 (10)	0.0275 (10)	0.0268 (10)	0.0004 (8)	0.0088 (8)	−0.0013 (8)
C9	0.0383 (11)	0.0327 (11)	0.0314 (11)	0.0013 (9)	0.0162 (9)	0.0046 (9)
C10	0.0326 (10)	0.0257 (10)	0.0460 (12)	−0.0034 (9)	0.0140 (9)	0.0053 (9)
C11	0.0322 (10)	0.0297 (11)	0.0319 (11)	−0.0064 (8)	0.0029 (8)	−0.0030 (8)
C12	0.0299 (10)	0.0293 (10)	0.0250 (9)	−0.0008 (8)	0.0060 (8)	0.0012 (8)
C13	0.0251 (9)	0.0294 (10)	0.0256 (9)	0.0010 (8)	0.0108 (7)	0.0060 (8)
C14	0.0265 (10)	0.0374 (12)	0.0571 (13)	−0.0021 (9)	0.0164 (9)	−0.0025 (10)
C15	0.0244 (10)	0.0573 (16)	0.0770 (16)	−0.0071 (11)	0.0170 (11)	0.0003 (13)
C16	0.0267 (11)	0.0609 (16)	0.0673 (15)	0.0102 (11)	0.0214 (11)	0.0186 (13)
C17	0.0437 (12)	0.0417 (13)	0.0516 (13)	0.0170 (11)	0.0285 (10)	0.0152 (10)
C18	0.0341 (10)	0.0313 (11)	0.0331 (11)	0.0008 (9)	0.0169 (8)	0.0034 (9)
C19	0.0318 (10)	0.0343 (11)	0.0334 (11)	0.0086 (9)	0.0113 (8)	0.0021 (9)
C20	0.0624 (15)	0.0318 (12)	0.0506 (13)	0.0106 (11)	0.0142 (11)	0.0014 (10)
C21	0.0675 (16)	0.0492 (14)	0.0397 (13)	0.0188 (12)	0.0176 (11)	−0.0022 (11)
C22	0.0397 (13)	0.0515 (15)	0.0967 (19)	0.0006 (12)	0.0295 (13)	−0.0100 (13)
O	0.0239 (6)	0.0260 (7)	0.0280 (7)	0.0030 (5)	0.0070 (5)	−0.0026 (5)
Si	0.0205 (2)	0.0252 (3)	0.0237 (3)	−0.0009 (2)	0.00684 (18)	−0.0001 (2)

C1—C2	1.389 (2)	C13—C14	1.388 (3)
C1—C6	1.393 (2)	C13—Si	1.8544 (17)
C1—Si	1.8626 (18)	C14—C15	1.371 (3)
C2—C3	1.375 (3)	C14—H14	0.95
C2—H2	0.95	C15—C16	1.378 (3)
C3—C4	1.376 (3)	C15—H15	0.95
C3—H3	0.95	C16—C17	1.362 (3)
C4—C5	1.366 (3)	C16—H16	0.95
C4—H4	0.95	C17—C18	1.382 (2)
C5—C6	1.375 (3)	C17—H17	0.95
C5—H5	0.95	C18—H18	0.95
C6—H6	0.95	C19—O	1.437 (2)
C7—C8	1.391 (2)	C19—C22	1.485 (3)
C7—C12	1.393 (2)	C19—C20	1.516 (3)
C7—Si	1.8549 (18)	C19—C21	1.524 (3)
C8—C9	1.376 (2)	C20—H20A	0.98
C8—H8	0.95	C20—H20B	0.98
C9—C10	1.374 (2)	C20—H20C	0.98
C9—H9	0.95	C21—H21A	0.98
C10—C11	1.373 (3)	C21—H21B	0.98
C10—H10	0.95	C21—H21C	0.98
C11—C12	1.376 (2)	C22—H22A	0.98
C11—H11	0.95	C22—H22B	0.98
C12—H12	0.95	C22—H22C	0.98
C13—C18	1.385 (2)	O—Si	1.6251 (12)
C2—C1—C6	117.08 (17)	C14—C15—H15	120
C2—C1—Si	120.00 (14)	C16—C15—H15	120
C6—C1—Si	122.90 (14)	C17—C16—C15	119.53 (19)
C3—C2—C1	121.4 (2)	C17—C16—H16	120.2
C3—C2—H2	119.3	C15—C16—H16	120.2
C1—C2—H2	119.3	C16—C17—C18	120.27 (19)
C2—C3—C4	119.9 (2)	C16—C17—H17	119.9
C2—C3—H3	120	C18—C17—H17	119.9
C4—C3—H3	120	C17—C18—C13	121.47 (18)
C5—C4—C3	120.0 (2)	C17—C18—H18	119.3
C5—C4—H4	120	C13—C18—H18	119.3
C3—C4—H4	120	O—C19—C22	110.67 (16)
C4—C5—C6	120.0 (2)	O—C19—C20	109.03 (15)
C4—C5—H5	120	C22—C19—C20	112.45 (17)
C6—C5—H5	120	O—C19—C21	104.93 (14)
C5—C6—C1	121.6 (2)	C22—C19—C21	109.93 (17)
C5—C6—H6	119.2	C20—C19—C21	109.56 (17)
C1—C6—H6	119.2	C19—C20—H20A	109.5
C8—C7—C12	116.97 (16)	C19—C20—H20B	109.5
C8—C7—Si	121.30 (13)	H20A—C20—H20B	109.5
C12—C7—Si	121.69 (13)	C19—C20—H20C	109.5
C9—C8—C7	121.87 (17)	H20A—C20—H20C	109.5
C9—C8—H8	119.1	H20B—C20—H20C	109.5
C7—C8—H8	119.1	C19—C21—H21A	109.5
C10—C9—C8	119.50 (17)	C19—C21—H21B	109.5
C10—C9—H9	120.3	H21A—C21—H21B	109.5
C8—C9—H9	120.3	C19—C21—H21C	109.5
C11—C10—C9	120.31 (17)	H21A—C21—H21C	109.5
C11—C10—H10	119.8	H21B—C21—H21C	109.5
C9—C10—H10	119.8	C19—C22—H22A	109.5
C10—C11—C12	119.81 (17)	C19—C22—H22B	109.5
C10—C11—H11	120.1	H22A—C22—H22B	109.5
C12—C11—H11	120.1	C19—C22—H22C	109.5
C11—C12—C7	121.52 (17)	H22A—C22—H22C	109.5
C11—C12—H12	119.2	H22B—C22—H22C	109.5
C7—C12—H12	119.2	C19—O—Si	135.97 (11)
C18—C13—C14	116.93 (16)	O—Si—C13	102.32 (7)
C18—C13—Si	122.11 (13)	O—Si—C7	111.33 (7)
C14—C13—Si	120.89 (14)	C13—Si—C7	109.98 (8)
C15—C14—C13	121.72 (19)	O—Si—C1	112.61 (7)
C15—C14—H14	119.1	C13—Si—C1	111.02 (8)
C13—C14—H14	119.1	C7—Si—C1	109.42 (8)
C14—C15—C16	120.1 (2)