Syntheses and crystal structures of 2-methyl-1,1,2,3,3-penta­phenyl-2-sila­propane and 2-methyl-1,1,3,3-tetra­phenyl-2-silapropan-2-ol

Williams, A.; Brown, M.; Staples, R.J.; Biros, S.M.; Winchester, W.R.

doi:10.1107/S2056989019011265

research communications

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ISSN: 2056-9890

Volume 75| Part 9| September 2019| Pages 1339-1343

https://doi.org/10.1107/S2056989019011265

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Syntheses and crystal structures of 2-methyl-1,1,2,3,3-pentaphenyl-2-silapropane and 2-methyl-1,1,3,3-tetraphenyl-2-silapropan-2-ol

Alexandra Williams,^a Michelle Brown,^a Richard J. Staples,^b Shannon M. Biros ^a and William R. Winchester ^a ^*

^aDepartment of Chemistry, Grand Valley State University, 1 Campus Dr., Allendale, MI 49401, USA, and ^bCenter for Crystallographic Research, Michigan State University, Department of Chemistry and Chemical Biology, East Lansing, MI 48824, USA
^*Correspondence e-mail: winchesr@gvsu.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 9 August 2019; accepted 12 August 2019; online 23 August 2019)

The sterically hindered silicon compound 2-methyl-1,1,2,3,3-pentaphenyl-2-silapropane, C₃₃H₃₀Si (I), was prepared via the reaction of two equivalents of diphenylmethyllithium (benzhydryllithium) and dichloromethylphenylsilane. This bisbenzhydryl-substituted silicon compound was then reacted with trifluoromethanesulfonic acid, followed by hydrolysis with water to give the silanol 2-methyl-1,1,3,3-tetraphenyl-2-silapropan-2-ol, C₂₇H₂₆OSi (II). Key geometric features for I are the Si—C bond lengths that range from 1.867 (2) to 1.914 (2) Å and a τ₄ descriptor for fourfold coordination around the Si atom of 0.97 (indicating a nearly perfect tetrahedron). Key geometric features for compound II include Si—C bond lengths that range from 1.835 (4) to 1.905 (3) Å, a Si—O bond length of 1.665 (3) Å, and a τ₄ descriptor for fourfold coordination around the Si atom of 0.96. In compound II, there is an intramolecular C—H⋯O hydrogen bond present. In the crystal of I, molecules are linked by two pairs of C—H⋯π interactions, forming dimers that are linked into ribbons propagating along the b-axis direction. In the crystal of II, molecules are linked by C—H⋯π and O—H⋯π interactions that result in the formation of ribbons that run along the a-axis direction.

Keywords: crystal structure; silanol; steric hindrance; diphenylmethyl; benzhydryl; O—H⋯π interaction; C—H⋯π interaction.

CCDC references: 1946744; 1946743

1. Chemical context

The benzhydryl substituent and its derivatives occur in many medicinal compounds, for example: diphenhydramine, modafinil and meclizine (Fig. 1). The addition of the benzhydryl group to a drug significantly increases its lipophilicity and the two aromatic rings add electron density and bulk. There is an active field looking at the switching of silicon for carbon to discover new medicinal compounds and there have been several recent publications and reviews in the area (Franz & Wilson, 2013 ; Geyer et al., 2015 ; Ramesh & Reddy, 2018 ; Tacke & Doerrich, 2016 ). It seemed to us that another option is to replace the sulfoxide group with a silanol, in which the silicon has a size that is similar to sulfur and the alcohol will occupy the space of the sulfoxide oxygen. The conversion of a phenylsilane to a silanol by the reaction with trifluoromethanesulfonic acid followed by hydrolysis has been used previously (Kira et al., 2007 ; Shainyan et al., 2017 ), and worked well for the introduction of the silanol in compound II, silanol 2-methyl-1,1,3,3-tetraphenyl-2-silapropan-2-ol.

Figure 1
The benzhydryl group in some representative medicinal compounds.

The steric bulk of the benzhydryl group has been used to advantage in several silyl reagents. It has been reported that the benzhydryldimethylsilylgroup is readily synthesized and undergoes facile oxidation with hydrogen peroxide to form alcohols (Peng & Woerpel, 2001 ). Yoshida and coworkers have started with a tris(diphenylmethyl)silane and further substituted aromatic rings using electrophilic aromatic substitution to produce the sterically demanding TEDAMS group (Terao et al., 2010 ). Unno et al. (2006 ) have addressed the influence of bulky silyl groups on the ability of silanols to hydrogen bond, and found that (i-Pr₃Si)₃SiOH exists as a monomer while (t-BuMe₂Si)₃SiOH is a hydrogen-bonded dimer. Our observation that compound II is monomeric indicates that the silicon atom is very hindered by the presence of the two benzhydryl groups.

2. Structural commentary

The molecular structure of compound I is shown in Fig. 2. The Si—C bond lengths range from 1.867 (2) to 1.914 (2) Å, with the Si—C1 bond to the methyl group being the shortest. The τ₄ descriptor for fourfold coordination around Si1 is 0.97, indicating a nearly perfect tetrahedral geometry around this silicon atom (where 0 = square planar, 0.85 = trigonal pyramidal, and 1 = tetrahedral; Yang et al., 2007 ). The Si1—C1 bond and aromatic ring (C4–C9) are nearly co-planar with a C1—Si1—C4—C5 torsion angle of 12.2 (2)°. The orientation of the benzhydryl group bonded to C2 is such that when the molecule is viewed down the C2—Si1 bond the methyl group (C1) is anti to H2 (torsion angle C1—Si1—C2—H2 is 169°), with the aromatic rings gauche. For the benzhydryl group containing C3, the hydrogen atom H3 is gauche to the methyl group (C1) with a C1—Si1—C3—H3 torsion angle of 69°, with the aromatic ring (C22–C27) occupying the anti position.

Figure 2
The molecular structure of compound I, with the atom-labeling scheme. Displacement ellipsoids are drawn at the 40% probability level. For clarity, the hydrogen atoms have been omitted.

The molecular structure of compound II is shown in Fig. 3. The Si—C bond lengths range from 1.835 (4) to 1.905 (3) Å, with an Si—O bond length of 1.665 (3) Å. The τ₄ descriptor for fourfold coordination around Si1 is 0.96, again indicating an almost perfect tetrahedral geometry around this silicon atom. The orientation of the C2 benzhydryl group is such that the hydrogen atom H2 is anti to the methyl group (C1) with a C1—Si1—C2—H2 torsion angle of −165°. For the benzhydryl group containing C3, the hydrogen atom H3 is again gauche to the methyl group (C1) with a C1—Si1—C3—H3 torsion angle of 55°, and the aromatic ring C22–C27 occupies the anti position. An intramolecular C—H⋯O hydrogen bond is present between H27 and O1 with an H⋯A distance of 2.55 Å (Table 2).

Table 2
Hydrogen-bond geometry (Å, °) for II

Cg1 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C27—H27⋯O1	0.93	2.55	3.237 (4)	131
O1—H1⋯Cg1ⁱ	0.75 (8)	2.70 (7)	3.416 (3)	162 (7)
C24—H24⋯Cg1ⁱⁱ	0.93	2.86	3.582 (4)	135
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z.

Figure 3
The molecular structure of compound II, with the atom-labeling scheme. Displacement ellipsoids are drawn at the 40% probability level. For clarity, the C-bound hydrogen atoms have been omitted.

3. Supramolecular features

In the crystal of I, molecules are linked by two pairs of intermolecular C—H⋯π interactions involving inversion-related compounds (Fig. 4 and Table 1). The result of these interactions is the formation of dimers that are linked to form ribbons along the b-axis direction (Fig. 5).

Table 1
Hydrogen-bond geometry (Å, °) for I

Cg2 and Cg4 are the centroids of the C10–C15 and C22–C27 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯Cg4ⁱ	0.95	2.94	3.716 (2)	140
C24—H24⋯Cg2ⁱⁱ	0.95	2.75	3.696 (2)	175
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+2, -y+1, -z.

Figure 4
Intermolecular C—H⋯π interactions present in the crystal of compound I; see Table 1

for details. Only hydrogen atoms H24 and H20 are shown for clarity, and the C—H⋯π interactions are depicted as purple lines. Symmetry codes: (i) −x + 2, −y, −z; (ii) −x + 2, −y + 1, −z.

Figure 5
The crystal packing of compound I, viewed along the a-axis, showing the supramolecular ribbons formed by intermolecular C—H⋯π interactions (Table 1

; shown as dashed purple lines). Only hydrogen atoms H20 and H24 are shown for clarity.

In the crystal of II, inversion-related molecules are linked by a pair of O—H⋯π interactions, forming dimers (Table 2, Fig. 6). Similar interactions between aryl groups and OH groups in silanols have been reported previously (Al-Juaid et al., 1992 ). In the crystal of II, the dimers are linked by a pair of C—H⋯π interactions (Table 2), so forming ribbons that propagate along the a-axis direction (Fig. 7).

Figure 6
Intramolecular hydrogen bond (blue dotted lines) and intermolecular C—H⋯π and O—H⋯π interactions (Table 2

; purple dashed lines) present in the crystal of compound II. For clarity, only hydrogen atoms H1, H24 and H27 have been included. Symmetry codes: (i) −x + 1, −y + 1, −z; (ii) −x, −y + 1, −z.

Figure 7
The crystal packing of compound II, viewed along the c-axis, showing the supramolecular ribbons formed by O—H⋯π and C—H⋯π interactions (Table 2

). For clarity, only hydrogen atoms H1, H24 and H27 have been included.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.40, May 2019; Groom et al., 2016 ) gave only one hit for a structure in which a silicon atom is bonded to two benzhydryl groups, viz. bis(diethylamino)bis(diphenylmethyl)silane (CSD refcode YEPTUI; Huppmann, et al., 1994 ). In this compound, the silicon atom is also bonded to two diethylamino groups. There are four other structures in the CSD with a silicon atom bonded to one benzhydryl group and a different alkyl group (this count excludes organometallic compounds). These compounds include, tert-butyl 1′-acetyl-4-[(diphenylmethyl)(dimethyl)silyl]-5′-fluoro-2′-oxo-1′,2′-dihydrospiro[cyclopentane-1,3′-indole]-2-carboxylate (SOSZIL; Ball-Jones et al., 2014 ), (3S,4R,5S)-4-[dimethyl(diphenylmethyl)silyl]-5-{[dimethyl(phenyl)silyl]methyl}-3-methyl-tetrahydrofuran-2-one (XICWUB; Peng & Woerpel, 2001), diphenyl(trimethylsilyl)methane (MOQWIY; Hill & Hitchcock, 2002 ) and diphenyl[t-butyl(dimethyl)silyl]methane (MOQWEU; Hill & Hitchcock, 2002). This search revealed zero structures in the CSD that contained a silanol group where the silicon atom is bonded to a benzhydryl group. However, the related structures (triphenylmethyl)silanetriol acetone solvate (GAWVUW; Kim, et al., 2005 ) and (triphenylmethyl)silanetriol tetrahydrofuran solvate (BAVQOF; Yoo, et al., 2001 ) are both silanetriols that bear a trityl group (–CPh₃) coordinated to the central silicon atom.

5. Synthesis and crystallization

Synthesis of 2-methyl-1,1,2,3,3-pentaphenyl-2-silapropane (I): Diphenylmethane (1.68 g, 10 mmol) was added to an oven-dried, argon-flushed 100 ml Schlenk flask along with a magnetic stirbar. Anhydrous tetrahydrofuran (10 ml) was then added to the flask to dissolve the solid and the solution was cooled to 273 K. After the solution had cooled for 10 min, n-butyllithium (6.25 ml, 1.6 M in hexanes, 10 mmol) was added and the solution was stirred for 1 h. The reaction mixture was then cooled further to 195 K and dichloromethylphenylsilane was added (0.955g, 5 mmol). After warming to room temperature and stirring for 12 h, the solution was poured into hexanes (20 ml) and the organic layer was washed with water (20 ml), dilute hydrochloric acid (3 N, 10 ml), water (10 ml) and finally brine (10 ml). The hexanes solution was dried over sodium sulfate, filtered and concentrated in vacuo. The product was purified by dissolving it in 20 ml hexane, cooling to 195 K and isolating the white crystals by filtration. The crystals were then washed with pentane and dried in vacuo (2.1 g, 93% yield). Colorless block-like crystals suitable for analysis by X-ray diffraction were grown by recrystallization of compound I (0.1 g) from hexanes (2 ml) with heating (0.08 g isolated yield). FT–IR (ν, cm⁻¹): 3057, 3019, 2869, 1597, 1493, 696; ¹H NMR (400 MHz, chloroform-d) δ 0.39 (s, 3H), 3.87 (s, 2H), 6.8–7.4 (m, 25H); ¹³C NMR (101 MHz, chloroform-d) δ −4.77, 42.70, 125.28, 125.67, 127.37, 128.14, 128.49, 129.21, 129.46, 129.81, 134.62, 135.99, 142.02, 142.14; ²⁹Si NMR (79 MHz, chloroform-d) δ −3.12.

Synthesis of 2-methyl-1,1,3,3-tetraphenyl-2-silapropan-2-ol (II): Bis(diphenylmethyl)methylphenylsilane (0.455 g, 1.0 mmol) was added to an oven-dried, argon-flushed 50 ml Schlenk flask along with a stirbar. Anhydrous toluene (5 ml) was added to dissolve the solid and the solution was cooled to 273 K. Trifluoromethanesulfonic acid was weighed in a vial (150 mg, 1 mmol) and then added to the Schlenk flask using a Pasteur pipette, at which point the solution went from colorless to a bright yellow. The solution was stirred for 2 h at room temperature after which time the solution went from cloudy to clear. At this point a mixture of water (40 mg, 2.2 mmol) and triethylamine (200 mg, 2.0 mmol) in ether (2 ml) was prepared and added to the rapidly stirring solution of the triflate in toluene, which caused the yellow solution to immediately turn colorless. After stirring for 1 h, the mixture was poured into hexanes (20 ml) and the organic layer was washed with water (20 ml), dilute hydrochloric acid (3 N, 10 ml), water (10 ml) and finally brine (10 ml). The hexanes solution was dried over sodium sulfate, filtered and the solvent was removed in vacuo. The crude product was then dissolved in 5 ml hexane and cooled to 195 K. The white crystals were isolated by vacuum filtration, washed with pentane and dried in vacuo (319 mg, 81% yield). Colourless block-like crystals suitable for analysis by X-ray diffraction were grown by recrystallization of compound II (0.4 g) from hexanes (5 ml) with heating (0.3 g isolated yield, m.p. (uncorrected) 375.8–376.2 K). FT–IR (ν, cm⁻¹): 3591, 3057, 3024, 1597, 1491, 696; ¹H NMR (400 MHz, chloroform-d) δ 0.15 (s, 3H), 3.49 (s, 2H), 7.22 (m, 20H). ¹³C NMR (101 MHz, chloroform-d) δ −2.34, 44.44, 125.64, 125.68, 128.62, 129.06, 129.28, 141.20, 141.43. ²⁹Si NMR (79 MHz, chloroform-d) δ 7.98.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. For both compounds, the hydrogen atoms bonded to carbon atoms were placed in calculated positions and refined as riding: C—H = 0.95–1.00 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms in compound I, and C—H = 0.93–0.98 Å with 1.2U_eq(C) in compound II. The hydrogen atom bonded to O1 (H1) in compound II was located in an electron-density difference map and freely refined.

Table 3
Experimental details

	I	II
Crystal data
Chemical formula	C₃₃H₃₀Si	C₂₇H₂₆OSi
M_r	454.66	394.57
Crystal system, space group	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁/c
Temperature (K)	173	173
a, b, c (Å)	10.3879 (7), 10.5037 (7), 13.6350 (9)	11.8576 (5), 13.2995 (6), 14.3948 (6)
α, β, γ (°)	68.8212 (7), 70.6364 (7), 84.7947 (8)	90, 110.363 (3), 90
V (Å³)	1308.06 (15)	2128.20 (16)
Z	2	4
Radiation type	Mo Kα	Cu Kα
μ (mm⁻¹)	0.11	1.08
Crystal size (mm)	0.21 × 0.21 × 0.17	0.10 × 0.09 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )	Multi-scan (SADABS; Bruker, 2013
T_min, T_max	0.695, 0.745	0.624, 0.754
No. of measured, independent and observed [I > 2σ(I)] reflections	16773, 4803, 3734	11901, 4113, 2414
R_int	0.036	0.096
(sin θ/λ)_max (Å⁻¹)	0.603	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.120, 1.08	0.062, 0.171, 0.97
No. of reflections	4803	4113
No. of parameters	308	267
H-atom treatment	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.22	0.29, −0.36
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ; Bourhis et al., 2015 ) and CrystalMaker (Palmer, 2007 ).

Supporting information

CCDC references: 1946744; 1946743

Crystal structure: contains datablocks Global, II, I. DOI: https://doi.org/10.1107/S2056989019011265/su5509sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019011265/su5509Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989019011265/su5509IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019011265/su5509Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989019011265/su5509IIsup5.cml

checkCIF report

Computing details top

For both structures, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015); software used to prepare material for publication: CrystalMaker (Palmer, 2007).

2-Methyl-1,1,2,3,3-pentaphenyl-2-silapropane (I) top

Crystal data top

C₃₃H₃₀Si	Z = 2
M_r = 454.66	F(000) = 484
Triclinic, P1	D_x = 1.154 Mg m⁻³
a = 10.3879 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5037 (7) Å	Cell parameters from 6620 reflections
c = 13.6350 (9) Å	θ = 2.2–25.4°
α = 68.8212 (7)°	µ = 0.11 mm⁻¹
β = 70.6364 (7)°	T = 173 K
γ = 84.7947 (8)°	Block, colourless
V = 1308.06 (15) Å³	0.21 × 0.21 × 0.17 mm

Data collection top

Bruker APEXII CCD diffractometer	3734 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.036
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θ_max = 25.4°, θ_min = 1.7°
T_min = 0.695, T_max = 0.745	h = −12→12
16773 measured reflections	k = −12→12
4803 independent reflections	l = −16→16

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0521P)² + 0.3536P] where P = (F_o² + 2F_c²)/3
4803 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Si1	0.75666 (5)	0.17147 (5)	0.27134 (4)	0.02998 (15)
C1	0.58208 (18)	0.0942 (2)	0.31735 (16)	0.0399 (5)
H1A	0.580675	0.040999	0.271655	0.060*
H1B	0.516044	0.166936	0.309113	0.060*
H1C	0.557892	0.034234	0.395435	0.060*
C2	0.78889 (17)	0.32685 (18)	0.13751 (14)	0.0293 (4)
H2	0.875549	0.371155	0.128137	0.035*
C3	0.88432 (17)	0.03163 (18)	0.25388 (14)	0.0290 (4)
H3	0.879419	0.013883	0.187902	0.035*
C4	0.77121 (19)	0.23587 (18)	0.37890 (15)	0.0337 (4)
C5	0.6560 (2)	0.2462 (2)	0.46416 (16)	0.0436 (5)
H5	0.569129	0.220352	0.467114	0.052*
C6	0.6643 (3)	0.2927 (2)	0.54426 (18)	0.0549 (6)
H6	0.583678	0.298764	0.601188	0.066*
C7	0.7882 (3)	0.3304 (2)	0.54221 (19)	0.0539 (6)
H7	0.793896	0.361141	0.598221	0.065*
C8	0.9045 (2)	0.3235 (2)	0.45856 (19)	0.0492 (6)
H8	0.990631	0.350498	0.456297	0.059*
C9	0.8961 (2)	0.2771 (2)	0.37750 (17)	0.0401 (5)
H9	0.976882	0.273302	0.319904	0.048*
C10	0.67921 (17)	0.43090 (18)	0.15447 (14)	0.0294 (4)
C11	0.55994 (19)	0.4316 (2)	0.12873 (16)	0.0361 (4)
H11	0.546285	0.365865	0.099890	0.043*
C12	0.46085 (19)	0.5266 (2)	0.14451 (16)	0.0415 (5)
H12	0.380019	0.525025	0.126874	0.050*
C13	0.4791 (2)	0.6233 (2)	0.18562 (16)	0.0416 (5)
H13	0.411325	0.688460	0.196376	0.050*
C14	0.5969 (2)	0.6242 (2)	0.21100 (16)	0.0403 (5)
H14	0.610168	0.690778	0.239220	0.048*
C15	0.69603 (19)	0.52935 (19)	0.19580 (15)	0.0348 (4)
H15	0.776475	0.531510	0.213801	0.042*
C16	0.81390 (17)	0.30119 (18)	0.02966 (15)	0.0302 (4)
C17	0.89389 (19)	0.3951 (2)	−0.06919 (16)	0.0395 (5)
H17	0.929517	0.474662	−0.068264	0.047*
C18	0.9227 (2)	0.3751 (2)	−0.16910 (17)	0.0481 (5)
H18	0.977671	0.440845	−0.235724	0.058*
C19	0.8724 (2)	0.2603 (2)	−0.17273 (17)	0.0458 (5)
H19	0.894110	0.245561	−0.241102	0.055*
C20	0.7903 (2)	0.1675 (2)	−0.07596 (18)	0.0454 (5)
H20	0.753497	0.089032	−0.077590	0.054*
C21	0.7611 (2)	0.1883 (2)	0.02404 (16)	0.0387 (5)
H21	0.703758	0.123685	0.090102	0.046*
C22	1.03391 (17)	0.06948 (17)	0.22632 (14)	0.0288 (4)
C23	1.10054 (19)	0.16811 (19)	0.12395 (15)	0.0365 (5)
H23	1.051484	0.211263	0.073556	0.044*
C24	1.2365 (2)	0.2044 (2)	0.09431 (17)	0.0438 (5)
H24	1.279369	0.272864	0.024624	0.053*
C25	1.3101 (2)	0.1413 (2)	0.16568 (18)	0.0446 (5)
H25	1.403699	0.165709	0.145408	0.054*
C26	1.2463 (2)	0.0427 (2)	0.26653 (17)	0.0421 (5)
H26	1.296597	−0.001657	0.315750	0.050*
C27	1.10940 (19)	0.00747 (19)	0.29711 (15)	0.0341 (4)
H27	1.066750	−0.060027	0.367444	0.041*
C28	0.82851 (17)	−0.09864 (18)	0.35234 (15)	0.0300 (4)
C29	0.80721 (19)	−0.10980 (19)	0.46160 (15)	0.0347 (4)
H29	0.833986	−0.035807	0.475796	0.042*
C30	0.74772 (19)	−0.2268 (2)	0.54981 (16)	0.0388 (5)
H30	0.734851	−0.232753	0.623661	0.047*
C31	0.7071 (2)	−0.3347 (2)	0.53092 (17)	0.0432 (5)
H31	0.664258	−0.414051	0.591663	0.052*
C32	0.7288 (2)	−0.3271 (2)	0.42349 (18)	0.0452 (5)
H32	0.702693	−0.401861	0.409890	0.054*
C33	0.78895 (19)	−0.20994 (19)	0.33547 (16)	0.0365 (4)
H33	0.803491	−0.205565	0.261749	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0258 (3)	0.0328 (3)	0.0277 (3)	0.0011 (2)	−0.0077 (2)	−0.0073 (2)
C1	0.0296 (10)	0.0442 (11)	0.0373 (11)	−0.0004 (9)	−0.0088 (9)	−0.0059 (9)
C2	0.0258 (9)	0.0315 (10)	0.0295 (10)	−0.0010 (7)	−0.0094 (8)	−0.0086 (8)
C3	0.0280 (9)	0.0321 (10)	0.0258 (9)	0.0014 (7)	−0.0088 (7)	−0.0092 (8)
C4	0.0377 (10)	0.0305 (10)	0.0282 (10)	0.0086 (8)	−0.0126 (8)	−0.0050 (8)
C5	0.0459 (12)	0.0458 (12)	0.0319 (11)	0.0053 (10)	−0.0075 (9)	−0.0111 (9)
C6	0.0677 (16)	0.0552 (14)	0.0333 (12)	0.0104 (12)	−0.0060 (11)	−0.0173 (11)
C7	0.0861 (19)	0.0466 (13)	0.0412 (13)	0.0236 (12)	−0.0339 (13)	−0.0222 (11)
C8	0.0592 (14)	0.0445 (12)	0.0609 (15)	0.0170 (11)	−0.0375 (12)	−0.0249 (11)
C9	0.0383 (11)	0.0410 (11)	0.0459 (12)	0.0115 (9)	−0.0176 (9)	−0.0196 (10)
C10	0.0282 (9)	0.0312 (9)	0.0241 (9)	−0.0005 (7)	−0.0076 (7)	−0.0048 (8)
C11	0.0328 (10)	0.0414 (11)	0.0353 (11)	0.0007 (8)	−0.0139 (8)	−0.0122 (9)
C12	0.0290 (10)	0.0557 (13)	0.0368 (11)	0.0079 (9)	−0.0134 (9)	−0.0120 (10)
C13	0.0374 (11)	0.0489 (12)	0.0340 (11)	0.0151 (9)	−0.0098 (9)	−0.0141 (10)
C14	0.0447 (12)	0.0412 (11)	0.0372 (11)	0.0068 (9)	−0.0121 (9)	−0.0184 (9)
C15	0.0340 (10)	0.0409 (11)	0.0305 (10)	0.0027 (8)	−0.0136 (8)	−0.0113 (9)
C16	0.0256 (9)	0.0351 (10)	0.0304 (10)	0.0053 (8)	−0.0119 (8)	−0.0106 (8)
C17	0.0360 (11)	0.0473 (12)	0.0336 (11)	−0.0033 (9)	−0.0106 (9)	−0.0121 (9)
C18	0.0414 (12)	0.0656 (15)	0.0312 (11)	−0.0012 (11)	−0.0091 (9)	−0.0118 (10)
C19	0.0427 (12)	0.0668 (15)	0.0368 (12)	0.0137 (11)	−0.0168 (10)	−0.0274 (11)
C20	0.0543 (13)	0.0442 (12)	0.0526 (14)	0.0126 (10)	−0.0287 (11)	−0.0263 (11)
C21	0.0429 (11)	0.0366 (11)	0.0365 (11)	0.0002 (9)	−0.0163 (9)	−0.0094 (9)
C22	0.0272 (9)	0.0292 (9)	0.0303 (10)	0.0055 (7)	−0.0085 (8)	−0.0126 (8)
C23	0.0324 (10)	0.0384 (11)	0.0302 (10)	0.0056 (8)	−0.0082 (8)	−0.0052 (9)
C24	0.0336 (11)	0.0433 (12)	0.0379 (12)	−0.0025 (9)	−0.0027 (9)	−0.0028 (9)
C25	0.0310 (11)	0.0460 (12)	0.0513 (13)	−0.0058 (9)	−0.0122 (10)	−0.0101 (10)
C26	0.0371 (11)	0.0444 (12)	0.0457 (12)	0.0000 (9)	−0.0211 (9)	−0.0096 (10)
C27	0.0350 (10)	0.0329 (10)	0.0317 (10)	−0.0004 (8)	−0.0112 (8)	−0.0075 (8)
C28	0.0239 (9)	0.0294 (9)	0.0328 (10)	0.0044 (7)	−0.0077 (8)	−0.0086 (8)
C29	0.0339 (10)	0.0343 (10)	0.0336 (10)	0.0046 (8)	−0.0097 (8)	−0.0112 (8)
C30	0.0337 (10)	0.0417 (11)	0.0306 (10)	0.0069 (9)	−0.0050 (8)	−0.0069 (9)
C31	0.0373 (11)	0.0367 (11)	0.0401 (12)	−0.0019 (9)	−0.0065 (9)	−0.0007 (9)
C32	0.0477 (12)	0.0345 (11)	0.0498 (13)	−0.0036 (9)	−0.0161 (10)	−0.0090 (10)
C33	0.0354 (10)	0.0367 (11)	0.0337 (11)	0.0015 (8)	−0.0090 (8)	−0.0104 (9)

Geometric parameters (Å, º) top

Si1—C1	1.8669 (18)	C15—H15	0.9500
Si1—C2	1.9099 (18)	C16—C17	1.388 (3)
Si1—C3	1.9138 (18)	C16—C21	1.387 (3)
Si1—C4	1.8744 (19)	C17—H17	0.9500
C1—H1A	0.9800	C17—C18	1.384 (3)
C1—H1B	0.9800	C18—H18	0.9500
C1—H1C	0.9800	C18—C19	1.380 (3)
C2—H2	1.0000	C19—H19	0.9500
C2—C10	1.526 (2)	C19—C20	1.376 (3)
C2—C16	1.524 (2)	C20—H20	0.9500
C3—H3	1.0000	C20—C21	1.388 (3)
C3—C22	1.527 (2)	C21—H21	0.9500
C3—C28	1.520 (2)	C22—C23	1.395 (2)
C4—C5	1.393 (3)	C22—C27	1.388 (3)
C4—C9	1.396 (3)	C23—H23	0.9500
C5—H5	0.9500	C23—C24	1.382 (3)
C5—C6	1.376 (3)	C24—H24	0.9500
C6—H6	0.9500	C24—C25	1.381 (3)
C6—C7	1.369 (3)	C25—H25	0.9500
C7—H7	0.9500	C25—C26	1.376 (3)
C7—C8	1.377 (3)	C26—H26	0.9500
C8—H8	0.9500	C26—C27	1.388 (3)
C8—C9	1.389 (3)	C27—H27	0.9500
C9—H9	0.9500	C28—C29	1.394 (3)
C10—C11	1.394 (2)	C28—C33	1.390 (3)
C10—C15	1.392 (3)	C29—H29	0.9500
C11—H11	0.9500	C29—C30	1.384 (3)
C11—C12	1.387 (3)	C30—H30	0.9500
C12—H12	0.9500	C30—C31	1.378 (3)
C12—C13	1.377 (3)	C31—H31	0.9500
C13—H13	0.9500	C31—C32	1.379 (3)
C13—C14	1.380 (3)	C32—H32	0.9500
C14—H14	0.9500	C32—C33	1.386 (3)
C14—C15	1.385 (3)	C33—H33	0.9500

C1—Si1—C2	111.34 (8)	C10—C15—H15	119.6
C1—Si1—C3	107.30 (9)	C14—C15—C10	120.79 (18)
C1—Si1—C4	109.22 (9)	C14—C15—H15	119.6
C2—Si1—C3	111.98 (8)	C17—C16—C2	118.87 (16)
C4—Si1—C2	106.03 (8)	C21—C16—C2	123.72 (16)
C4—Si1—C3	110.98 (8)	C21—C16—C17	117.42 (17)
Si1—C1—H1A	109.5	C16—C17—H17	119.4
Si1—C1—H1B	109.5	C18—C17—C16	121.26 (19)
Si1—C1—H1C	109.5	C18—C17—H17	119.4
H1A—C1—H1B	109.5	C17—C18—H18	119.7
H1A—C1—H1C	109.5	C19—C18—C17	120.5 (2)
H1B—C1—H1C	109.5	C19—C18—H18	119.7
Si1—C2—H2	105.2	C18—C19—H19	120.5
C10—C2—Si1	109.56 (11)	C20—C19—C18	119.09 (19)
C10—C2—H2	105.2	C20—C19—H19	120.5
C16—C2—Si1	117.65 (12)	C19—C20—H20	119.9
C16—C2—H2	105.2	C19—C20—C21	120.20 (19)
C16—C2—C10	112.90 (14)	C21—C20—H20	119.9
Si1—C3—H3	105.4	C16—C21—C20	121.47 (18)
C22—C3—Si1	116.07 (12)	C16—C21—H21	119.3
C22—C3—H3	105.4	C20—C21—H21	119.3
C28—C3—Si1	107.51 (11)	C23—C22—C3	119.13 (16)
C28—C3—H3	105.4	C27—C22—C3	123.19 (16)
C28—C3—C22	116.09 (14)	C27—C22—C23	117.65 (16)
C5—C4—Si1	120.97 (15)	C22—C23—H23	119.3
C5—C4—C9	116.66 (18)	C24—C23—C22	121.36 (18)
C9—C4—Si1	122.36 (15)	C24—C23—H23	119.3
C4—C5—H5	119.0	C23—C24—H24	119.9
C6—C5—C4	122.0 (2)	C25—C24—C23	120.21 (18)
C6—C5—H5	119.0	C25—C24—H24	119.9
C5—C6—H6	119.9	C24—C25—H25	120.4
C7—C6—C5	120.3 (2)	C26—C25—C24	119.18 (18)
C7—C6—H6	119.9	C26—C25—H25	120.4
C6—C7—H7	120.2	C25—C26—H26	119.6
C6—C7—C8	119.7 (2)	C25—C26—C27	120.72 (19)
C8—C7—H7	120.2	C27—C26—H26	119.6
C7—C8—H8	120.0	C22—C27—H27	119.6
C7—C8—C9	120.0 (2)	C26—C27—C22	120.87 (17)
C9—C8—H8	120.0	C26—C27—H27	119.6
C4—C9—H9	119.3	C29—C28—C3	122.69 (16)
C8—C9—C4	121.4 (2)	C33—C28—C3	119.78 (16)
C8—C9—H9	119.3	C33—C28—C29	117.43 (17)
C11—C10—C2	121.61 (16)	C28—C29—H29	119.4
C15—C10—C2	120.62 (16)	C30—C29—C28	121.16 (18)
C15—C10—C11	117.78 (17)	C30—C29—H29	119.4
C10—C11—H11	119.4	C29—C30—H30	119.9
C12—C11—C10	121.14 (18)	C31—C30—C29	120.25 (19)
C12—C11—H11	119.4	C31—C30—H30	119.9
C11—C12—H12	119.8	C30—C31—H31	120.1
C13—C12—C11	120.32 (18)	C30—C31—C32	119.74 (18)
C13—C12—H12	119.8	C32—C31—H31	120.1
C12—C13—H13	120.4	C31—C32—H32	120.1
C12—C13—C14	119.21 (18)	C31—C32—C33	119.76 (19)
C14—C13—H13	120.4	C33—C32—H32	120.1
C13—C14—H14	119.6	C28—C33—H33	119.2
C13—C14—C15	120.76 (19)	C32—C33—C28	121.64 (19)
C15—C14—H14	119.6	C32—C33—H33	119.2

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the C10–C15 and C22–C27 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···Cg4ⁱ	0.95	2.94	3.716 (2)	140
C24—H24···Cg2ⁱⁱ	0.95	2.75	3.696 (2)	175

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+2, −y+1, −z.

2-Methyl-1,1,3,3-tetraphenyl-2-silapropan-2-ol (II) top

Crystal data top

C₂₇H₂₆OSi	F(000) = 840
M_r = 394.57	D_x = 1.231 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 11.8576 (5) Å	Cell parameters from 1512 reflections
b = 13.2995 (6) Å	θ = 4.0–71.6°
c = 14.3948 (6) Å	µ = 1.08 mm⁻¹
β = 110.363 (3)°	T = 173 K
V = 2128.20 (16) Å³	Block, colourless
Z = 4	0.10 × 0.09 × 0.08 mm

Data collection top

Bruker APEXII CCD diffractometer	2414 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.096
Absorption correction: multi-scan (SADABS; Bruker, 2013	θ_max = 72.1°, θ_min = 4.0°
T_min = 0.624, T_max = 0.754	h = −14→14
11901 measured reflections	k = −14→16
4113 independent reflections	l = −17→16

Refinement top

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)] = 0.062	Hydrogen site location: mixed
wR(F²) = 0.171	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.0793P)²] where P = (F_o² + 2F_c²)/3
4113 reflections	(Δ/σ)_max = 0.001
267 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Si1	0.37978 (7)	0.60730 (7)	0.11066 (6)	0.0322 (2)
O1	0.4586 (2)	0.5078 (2)	0.0982 (2)	0.0478 (7)
H1	0.525 (6)	0.511 (5)	0.125 (5)	0.14 (3)*
C1	0.4582 (3)	0.7247 (3)	0.1046 (3)	0.0496 (10)
H1A	0.538510	0.722512	0.152061	0.074*
H1B	0.415753	0.780473	0.119230	0.074*
H1C	0.461428	0.732630	0.039250	0.074*
C2	0.2251 (3)	0.5965 (3)	0.0102 (2)	0.0311 (7)
H2	0.186321	0.541154	0.032661	0.037*
C3	0.3493 (3)	0.6018 (3)	0.2320 (2)	0.0305 (7)
H3	0.304983	0.663543	0.233789	0.037*
C4	0.2310 (3)	0.5599 (3)	−0.0879 (2)	0.0314 (7)
C5	0.2221 (3)	0.4579 (3)	−0.1059 (3)	0.0465 (9)
H5	0.212646	0.415105	−0.058001	0.056*
C6	0.2269 (4)	0.4173 (3)	−0.1928 (3)	0.0597 (12)
H6	0.220922	0.348044	−0.202343	0.072*
C7	0.2403 (4)	0.4783 (4)	−0.2651 (3)	0.0594 (12)
H7	0.242726	0.451111	−0.323899	0.071*
C8	0.2500 (4)	0.5796 (4)	−0.2490 (3)	0.0558 (11)
H8	0.259536	0.621704	−0.297355	0.067*
C9	0.2457 (3)	0.6210 (3)	−0.1611 (3)	0.0446 (9)
H9	0.252840	0.690203	−0.151519	0.054*
C10	0.1461 (3)	0.6868 (3)	0.0079 (2)	0.0318 (7)
C11	0.1675 (3)	0.7822 (3)	−0.0220 (3)	0.0402 (8)
H11	0.233780	0.792719	−0.041198	0.048*
C12	0.0917 (3)	0.8616 (3)	−0.0236 (3)	0.0478 (9)
H12	0.106084	0.924134	−0.046117	0.057*
C13	−0.0053 (3)	0.8494 (3)	0.0078 (3)	0.0495 (10)
H13	−0.055857	0.903091	0.006978	0.059*
C14	−0.0253 (3)	0.7557 (3)	0.0404 (3)	0.0463 (9)
H14	−0.089227	0.746580	0.062864	0.056*
C15	0.0485 (3)	0.6755 (3)	0.0402 (2)	0.0379 (8)
H15	0.032870	0.612895	0.061775	0.046*
C16	0.4654 (3)	0.6075 (3)	0.3226 (2)	0.0330 (7)
C17	0.5172 (3)	0.7002 (3)	0.3555 (3)	0.0417 (9)
H17	0.482228	0.758048	0.321262	0.050*
C18	0.6206 (3)	0.7080 (3)	0.4391 (3)	0.0517 (10)
H18	0.655291	0.770730	0.459002	0.062*
C19	0.6718 (3)	0.6238 (3)	0.4923 (3)	0.0483 (10)
H19	0.739662	0.629258	0.549267	0.058*
C20	0.6213 (3)	0.5311 (3)	0.4603 (3)	0.0485 (10)
H20	0.656040	0.473577	0.495283	0.058*
C21	0.5185 (3)	0.5229 (3)	0.3757 (3)	0.0402 (8)
H21	0.485335	0.459927	0.354838	0.048*
C22	0.2661 (3)	0.5165 (3)	0.2345 (2)	0.0330 (7)
C23	0.1654 (3)	0.5350 (3)	0.2610 (2)	0.0401 (8)
H23	0.151976	0.599365	0.280198	0.048*
C24	0.0848 (3)	0.4581 (3)	0.2589 (3)	0.0503 (10)
H24	0.018734	0.471259	0.277708	0.060*
C25	0.1022 (3)	0.3627 (3)	0.2294 (3)	0.0507 (11)
H25	0.047234	0.311931	0.226694	0.061*
C26	0.2021 (4)	0.3430 (3)	0.2038 (3)	0.0459 (9)
H26	0.214929	0.278564	0.184382	0.055*
C27	0.2826 (3)	0.4188 (3)	0.2069 (2)	0.0401 (8)
H27	0.349762	0.404301	0.190084	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0319 (4)	0.0348 (5)	0.0275 (4)	0.0005 (4)	0.0074 (3)	0.0024 (4)
O1	0.0406 (14)	0.0544 (18)	0.0440 (15)	0.0134 (13)	0.0092 (12)	−0.0039 (13)
C1	0.056 (2)	0.052 (3)	0.0361 (19)	−0.0172 (19)	0.0088 (17)	0.0081 (19)
C2	0.0329 (15)	0.0312 (18)	0.0273 (15)	−0.0035 (14)	0.0080 (12)	0.0031 (15)
C3	0.0369 (15)	0.0296 (17)	0.0250 (15)	0.0011 (14)	0.0109 (13)	−0.0004 (14)
C4	0.0295 (14)	0.0357 (19)	0.0259 (15)	0.0000 (14)	0.0057 (12)	−0.0012 (15)
C5	0.057 (2)	0.038 (2)	0.044 (2)	0.0052 (18)	0.0170 (18)	−0.0050 (18)
C6	0.064 (3)	0.048 (3)	0.065 (3)	0.000 (2)	0.020 (2)	−0.020 (2)
C7	0.051 (2)	0.075 (3)	0.052 (2)	−0.009 (2)	0.018 (2)	−0.030 (3)
C8	0.061 (2)	0.074 (3)	0.036 (2)	−0.016 (2)	0.0224 (18)	−0.008 (2)
C9	0.056 (2)	0.043 (2)	0.0346 (18)	−0.0080 (18)	0.0161 (16)	−0.0049 (18)
C10	0.0341 (15)	0.0340 (19)	0.0224 (15)	0.0024 (14)	0.0035 (12)	0.0004 (14)
C11	0.0462 (18)	0.034 (2)	0.043 (2)	0.0005 (16)	0.0191 (16)	0.0010 (17)
C12	0.057 (2)	0.033 (2)	0.053 (2)	0.0039 (17)	0.0201 (19)	0.0022 (19)
C13	0.053 (2)	0.040 (2)	0.052 (2)	0.0144 (18)	0.0137 (19)	−0.0072 (19)
C14	0.0429 (19)	0.051 (3)	0.047 (2)	0.0037 (17)	0.0176 (17)	−0.0020 (19)
C15	0.0401 (17)	0.036 (2)	0.0361 (18)	0.0022 (15)	0.0110 (14)	0.0023 (16)
C16	0.0344 (15)	0.042 (2)	0.0239 (14)	0.0003 (15)	0.0117 (12)	0.0022 (15)
C17	0.0471 (19)	0.039 (2)	0.0362 (18)	−0.0033 (16)	0.0111 (15)	−0.0015 (17)
C18	0.052 (2)	0.060 (3)	0.038 (2)	−0.018 (2)	0.0100 (17)	−0.009 (2)
C19	0.0381 (17)	0.073 (3)	0.0287 (17)	−0.0061 (19)	0.0054 (14)	0.001 (2)
C20	0.0407 (18)	0.063 (3)	0.0373 (19)	0.0030 (19)	0.0075 (16)	0.012 (2)
C21	0.0386 (17)	0.043 (2)	0.0353 (18)	−0.0004 (16)	0.0085 (15)	0.0046 (17)
C22	0.0366 (16)	0.0341 (19)	0.0239 (15)	−0.0030 (14)	0.0051 (13)	0.0058 (15)
C23	0.0424 (18)	0.045 (2)	0.0290 (17)	0.0017 (16)	0.0072 (14)	0.0034 (16)
C24	0.0377 (18)	0.070 (3)	0.039 (2)	−0.0073 (19)	0.0075 (16)	0.009 (2)
C25	0.052 (2)	0.052 (3)	0.0356 (19)	−0.0222 (19)	−0.0008 (17)	0.0107 (18)
C26	0.063 (2)	0.033 (2)	0.0337 (18)	−0.0076 (18)	0.0068 (17)	0.0041 (17)
C27	0.0480 (19)	0.037 (2)	0.0341 (18)	0.0006 (16)	0.0128 (15)	0.0073 (16)

Geometric parameters (Å, º) top

Si1—O1	1.666 (3)	C12—H12	0.9300
Si1—C1	1.835 (4)	C12—C13	1.384 (5)
Si1—C2	1.905 (3)	C13—H13	0.9300
Si1—C3	1.904 (3)	C13—C14	1.380 (5)
O1—H1	0.75 (6)	C14—H14	0.9300
C1—H1A	0.9600	C14—C15	1.380 (5)
C1—H1B	0.9600	C15—H15	0.9300
C1—H1C	0.9600	C16—C17	1.385 (5)
C2—H2	0.9800	C16—C21	1.383 (5)
C2—C4	1.518 (4)	C17—H17	0.9300
C2—C10	1.517 (4)	C17—C18	1.391 (5)
C3—H3	0.9800	C18—H18	0.9300
C3—C16	1.533 (4)	C18—C19	1.374 (5)
C3—C22	1.513 (4)	C19—H19	0.9300
C4—C5	1.378 (5)	C19—C20	1.378 (6)
C4—C9	1.389 (5)	C20—H20	0.9300
C5—H5	0.9300	C20—C21	1.396 (5)
C5—C6	1.382 (5)	C21—H21	0.9300
C6—H6	0.9300	C22—C23	1.396 (5)
C6—C7	1.372 (6)	C22—C27	1.392 (5)
C7—H7	0.9300	C23—H23	0.9300
C7—C8	1.366 (6)	C23—C24	1.394 (5)
C8—H8	0.9300	C24—H24	0.9300
C8—C9	1.397 (5)	C24—C25	1.376 (6)
C9—H9	0.9300	C25—H25	0.9300
C10—C11	1.391 (5)	C25—C26	1.383 (6)
C10—C15	1.397 (4)	C26—H26	0.9300
C11—H11	0.9300	C26—C27	1.378 (5)
C11—C12	1.381 (5)	C27—H27	0.9300

O1—Si1—C1	111.00 (17)	C11—C12—H12	119.5
O1—Si1—C2	106.65 (15)	C11—C12—C13	121.0 (4)
O1—Si1—C3	111.15 (15)	C13—C12—H12	119.5
C1—Si1—C2	113.46 (16)	C12—C13—H13	120.7
C1—Si1—C3	109.71 (16)	C14—C13—C12	118.5 (4)
C3—Si1—C2	104.69 (14)	C14—C13—H13	120.7
Si1—O1—H1	116 (5)	C13—C14—H14	119.6
Si1—C1—H1A	109.5	C15—C14—C13	120.8 (4)
Si1—C1—H1B	109.5	C15—C14—H14	119.6
Si1—C1—H1C	109.5	C10—C15—H15	119.4
H1A—C1—H1B	109.5	C14—C15—C10	121.1 (3)
H1A—C1—H1C	109.5	C14—C15—H15	119.4
H1B—C1—H1C	109.5	C17—C16—C3	119.7 (3)
Si1—C2—H2	104.2	C21—C16—C3	122.1 (3)
C4—C2—Si1	112.7 (2)	C21—C16—C17	118.2 (3)
C4—C2—H2	104.2	C16—C17—H17	119.5
C10—C2—Si1	112.4 (2)	C16—C17—C18	121.0 (4)
C10—C2—H2	104.2	C18—C17—H17	119.5
C10—C2—C4	117.5 (3)	C17—C18—H18	119.8
Si1—C3—H3	105.5	C19—C18—C17	120.5 (4)
C16—C3—Si1	112.2 (2)	C19—C18—H18	119.8
C16—C3—H3	105.5	C18—C19—H19	120.5
C22—C3—Si1	112.6 (2)	C18—C19—C20	119.1 (3)
C22—C3—H3	105.5	C20—C19—H19	120.5
C22—C3—C16	114.6 (3)	C19—C20—H20	119.7
C5—C4—C2	117.7 (3)	C19—C20—C21	120.5 (4)
C5—C4—C9	117.1 (3)	C21—C20—H20	119.7
C9—C4—C2	125.2 (3)	C16—C21—C20	120.7 (4)
C4—C5—H5	119.0	C16—C21—H21	119.7
C4—C5—C6	122.0 (4)	C20—C21—H21	119.7
C6—C5—H5	119.0	C23—C22—C3	120.1 (3)
C5—C6—H6	119.7	C27—C22—C3	122.4 (3)
C7—C6—C5	120.5 (4)	C27—C22—C23	117.5 (3)
C7—C6—H6	119.7	C22—C23—H23	119.7
C6—C7—H7	120.6	C24—C23—C22	120.7 (4)
C8—C7—C6	118.7 (4)	C24—C23—H23	119.7
C8—C7—H7	120.6	C23—C24—H24	119.7
C7—C8—H8	119.5	C25—C24—C23	120.5 (4)
C7—C8—C9	121.0 (4)	C25—C24—H24	119.7
C9—C8—H8	119.5	C24—C25—H25	120.3
C4—C9—C8	120.7 (4)	C24—C25—C26	119.5 (4)
C4—C9—H9	119.7	C26—C25—H25	120.3
C8—C9—H9	119.7	C25—C26—H26	120.0
C11—C10—C2	123.5 (3)	C27—C26—C25	120.0 (4)
C11—C10—C15	117.5 (3)	C27—C26—H26	120.0
C15—C10—C2	119.0 (3)	C22—C27—H27	119.1
C10—C11—H11	119.5	C26—C27—C22	121.9 (4)
C12—C11—C10	121.0 (3)	C26—C27—H27	119.1
C12—C11—H11	119.5

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C27—H27···O1	0.93	2.55	3.237 (4)	131
O1—H1···Cg1ⁱ	0.75 (8)	2.70 (7)	3.416 (3)	162 (7)
C24—H24···Cg1ⁱⁱ	0.93	2.86	3.582 (4)	135

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z.

Acknowledgements

The authors thank Pfizer, Inc., for the donation of a Varian INOVA 400 MHz NMR. The CCD-based diffractometers at Michigan State University were upgraded and/or replaced with departmental funds.

Funding information

Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences ( grant No. MRI CHE-1725699); Grand Valley State University (grant No. OURS, CSCE, Chemistry Department's Weldon Fund).

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Volume 75| Part 9| September 2019| Pages 1339-1343

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Syntheses and crystal structures of 2-methyl-1,1,2,3,3-penta­phenyl-2-sila­propane and 2-methyl-1,1,3,3-tetra­phenyl-2-silapropan-2-ol

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

Funding information

References

research communications

Syntheses and crystal structures of 2-methyl-1,1,2,3,3-pentaphenyl-2-silapropane and 2-methyl-1,1,3,3-tetraphenyl-2-silapropan-2-ol

3. Supramolecular features