organic compounds
The tert-butyldiphenylsilyl)oxy]-1,2-diphenylethan-1-one
of 2-[(aDepartment of Chemistry, Fordham University, 441 East Fordham Road, Bronx, NY 10458, USA
*Correspondence e-mail: pcorfield@fordham.edu
The title compound, C30H30O2Si, was synthesized and structurally characterized in order to determine the influence of the bulky silyl protecting group on the conformation of the benzoin moiety, with a view to directing the stereochemistry of the borohydride reduction of the benzoin. The shows a benzoin O—C—C—O torsion angle of 38.34 (1)°, not greatly different from that found in benzoin itself. In the crystal, a weak C—H⋯O hydrogen bond between the carbonyl group and a phenyl H atom of a symmetry-related molecule forms chains along [100].
Keywords: crystal structure; benzoin; silyl derivative; bulky group; conformation.
CCDC reference: 1908808
Structure description
As part of a program designed to alter the stereoselectivity of the reduction of benzoin derivatives, the oxysilyl benzoin derivative named in the title was synthesized in an attempt to explore the stereochemical effect of the large hydroxyl-protecting silyl group. The stereochemistry of this reduction can be explained by the Felkin–Anh or the Cram ). Given the need for a method that would afford the alternate racemic diols, the bulky silyl protecting group tert-butyldiphenylsilyl (TBDPS) was introduced with the expectation that this large substituent would allow for the production of the alternate diastereoisomer (as a racemic mixture). In the reported here (Fig. 1), however, the conformation is close to that of benzoin itself (Haisa et al., 1980; Fajardo et al., 1984; Solé et al., 1998) in spite of the presence of the TBDPS group and the differing crystalline environments of the two molecules. The O1—C1—C2—O2 torsion angle of 38.34 (16)° and the torsion angle C3—C1—C2—C9 between the ethane phenyl groups of 96.20 (13)° in the present structure are similar to the corresponding values of 26.4 and 85.5° given for benzoin. The phenyl ring on C1 in the present structure is almost co-planar with the sp2 plane at C1, with an angle of 12.68 (5)° between the plane through the phenyl group and the best plane through C1/O1/C2/O9. This leads to the short intramolecular contact H2 ⋯ H8 = 2.04 Å. In benzoin this phenyl group is twisted 11.6° from the sp2 C1 plane, with an H ⋯ H distance of 2.36 Å. The phenyl group bonded to C2 in the present structure is oriented so as to almost eclipse the C2—O2 bond, with torsion angle O2—C2—C9—C10 = −9.07 (16)°, which brings the H10 ⋯ O2 distance to 2.40 Å. This orientation is not however seen in the benzoin structure, where the corresponding torsion angle is −48.4°.
model (Rowland, 1983Formation of the silyloxy derivative prohibits the strong O—H⋯O hydrogen bonding expected in benzoin and its other derivatives, but a C=O ⋯H—C intermolecular interaction is seen (Table 1 and Fig. 2), linking the molecules in chains along the a-axis direction. Only three intermolecular H ⋯ H contacts are closer than 2.6 Å, with the shortest contact H4 ⋯ H12(x,1 + y,z) at 2.48 Å.
The stereochemical outcome of the reduction of the title compound will be reported elsewhere.
Synthesis and crystallization
The title compound was easily prepared in high yield (t-butyldiphenylsilyl chloride (TBDPS-Cl), imidazole, (±)-benzoin, DMF, RT) from (±)-benzoin and was isolated after as a low-melting, crystalline solid. Suitable crystals were obtained by recrystallization from hexanes (m.p. 346–345 K).
1H (400 MHz) NMR spectra were recorded on a Bruker Avance 400 spectrometer in CDCl3 with tetramethylsilane (TMS) as the internal standard, and chemical shifts are reported in parts per million (p.p.m., δ): 7.57–7.69 ppm, 2H, m; 7.51–7.55 ppm, 4H, m; 7.23–7.47 ppm, 14H, m; 5.82 ppm, 1H, s; 1.08 ppm, 9H, s. An infrared spectrum obtained with a Nicolet iS50 FT–IR machine showed μ(C=O) at 1694 cm−1.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1908808
https://doi.org/10.1107/S2414314619004784/lh4045sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619004784/lh4045Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314619004784/lh4045Isup3.cml
Data collection: KappaCCD Server Software (Nonius, 1997); cell
SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).C30H30O2Si | Z = 2 |
Mr = 450.63 | F(000) = 480 |
Triclinic, P1 | Dx = 1.155 Mg m−3 |
a = 10.3403 (3) Å | Mo Kα radiation, λ = 0.71070 Å |
b = 10.3926 (3) Å | Cell parameters from 4557 reflections |
c = 14.1442 (3) Å | θ = 1.0–25.0° |
α = 78.9928 (14)° | µ = 0.11 mm−1 |
β = 83.6739 (15)° | T = 300 K |
γ = 60.2736 (11)° | Block, colorless |
V = 1295.45 (6) Å3 | 0.5 × 0.4 × 0.2 mm |
Enraf–Nonius KappaCCD diffractometer | 5246 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.7°, θmin = 2.3° |
Detector resolution: 9 pixels mm-1 | h = 0→13 |
combination of ω and φ scans | k = −11→13 |
6102 measured reflections | l = −18→18 |
6102 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.060P)2 + 0.290P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
6102 reflections | Δρmax = 0.27 e Å−3 |
301 parameters | Δρmin = −0.18 e Å−3 |
0 restraints |
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. |
Refinement. H atoms were placed at ideal positions and refined riding on their parent C atoms, with C—H distances of 0.93 Å for the phenyl H atoms, 0.96 Å for the methyl H atoms and 0.98 Å for the methine H atom H2. Uiso values of the H atoms were set at 1.2xUeq(C) or 1.5xUeq(Cmethyl) of the bonded atoms. |
x | y | z | Uiso*/Ueq | ||
Si1 | 0.28262 (4) | 0.65987 (4) | 0.79919 (2) | 0.03862 (11) | |
O1 | 0.01496 (12) | 0.63949 (13) | 0.63925 (9) | 0.0617 (3) | |
O2 | 0.21373 (11) | 0.71114 (10) | 0.68988 (6) | 0.0429 (2) | |
C1 | 0.14561 (15) | 0.55370 (15) | 0.62691 (9) | 0.0412 (3) | |
C2 | 0.25752 (14) | 0.61237 (14) | 0.62185 (9) | 0.0362 (3) | |
H2 | 0.357881 | 0.528187 | 0.635855 | 0.043* | |
C3 | 0.19912 (16) | 0.39651 (15) | 0.61292 (10) | 0.0436 (3) | |
C4 | 0.0932 (2) | 0.35680 (19) | 0.59831 (13) | 0.0591 (4) | |
H4 | −0.007416 | 0.427740 | 0.597544 | 0.071* | |
C5 | 0.1373 (3) | 0.2125 (2) | 0.58496 (16) | 0.0779 (6) | |
H5 | 0.066449 | 0.187090 | 0.573793 | 0.093* | |
C6 | 0.2845 (3) | 0.1068 (2) | 0.58808 (17) | 0.0820 (6) | |
H6 | 0.313308 | 0.009475 | 0.579652 | 0.098* | |
C7 | 0.3901 (2) | 0.1432 (2) | 0.60358 (17) | 0.0760 (5) | |
H7 | 0.490202 | 0.070587 | 0.606047 | 0.091* | |
C8 | 0.34815 (19) | 0.28761 (17) | 0.61550 (13) | 0.0588 (4) | |
H8 | 0.420262 | 0.312108 | 0.625342 | 0.071* | |
C9 | 0.25367 (13) | 0.69454 (14) | 0.52002 (9) | 0.0364 (3) | |
C10 | 0.19247 (16) | 0.84890 (16) | 0.50123 (10) | 0.0462 (3) | |
H10 | 0.154230 | 0.904214 | 0.551675 | 0.055* | |
C11 | 0.18776 (19) | 0.92173 (18) | 0.40766 (12) | 0.0591 (4) | |
H11 | 0.148554 | 1.025326 | 0.395693 | 0.071* | |
C12 | 0.24112 (19) | 0.8407 (2) | 0.33231 (11) | 0.0636 (4) | |
H12 | 0.237759 | 0.889559 | 0.269512 | 0.076* | |
C13 | 0.29938 (19) | 0.6874 (2) | 0.35035 (11) | 0.0606 (4) | |
H13 | 0.333830 | 0.632934 | 0.299448 | 0.073* | |
C14 | 0.30696 (16) | 0.61416 (17) | 0.44335 (10) | 0.0487 (3) | |
H14 | 0.347958 | 0.510344 | 0.454959 | 0.058* | |
C15 | 0.46458 (15) | 0.65965 (16) | 0.78902 (10) | 0.0435 (3) | |
C16 | 0.51811 (16) | 0.69987 (16) | 0.69988 (10) | 0.0476 (3) | |
H16 | 0.463805 | 0.723616 | 0.644968 | 0.057* | |
C17 | 0.6500 (2) | 0.7053 (2) | 0.69108 (13) | 0.0650 (4) | |
H17 | 0.684405 | 0.730468 | 0.630669 | 0.078* | |
C18 | 0.7301 (2) | 0.6735 (3) | 0.77164 (16) | 0.0814 (6) | |
H18 | 0.817611 | 0.679282 | 0.765984 | 0.098* | |
C19 | 0.6807 (2) | 0.6332 (3) | 0.86067 (15) | 0.0875 (7) | |
H19 | 0.734885 | 0.611584 | 0.915286 | 0.105* | |
C20 | 0.5509 (2) | 0.6250 (2) | 0.86883 (12) | 0.0670 (5) | |
H20 | 0.519897 | 0.595383 | 0.929264 | 0.080* | |
C21 | 0.31257 (17) | 0.46557 (17) | 0.84700 (9) | 0.0477 (3) | |
C22 | 0.1945 (2) | 0.4339 (2) | 0.85593 (13) | 0.0671 (5) | |
H22 | 0.098158 | 0.512169 | 0.843669 | 0.081* | |
C23 | 0.2182 (3) | 0.2883 (3) | 0.88267 (16) | 0.0908 (7) | |
H23 | 0.138077 | 0.270004 | 0.888059 | 0.109* | |
C24 | 0.3597 (4) | 0.1713 (3) | 0.90119 (17) | 0.1016 (8) | |
H24 | 0.375578 | 0.073612 | 0.918301 | 0.122* | |
C25 | 0.4775 (3) | 0.1987 (2) | 0.89439 (16) | 0.0878 (7) | |
H25 | 0.573134 | 0.119791 | 0.907816 | 0.105* | |
C26 | 0.4540 (2) | 0.34389 (19) | 0.86758 (11) | 0.0610 (4) | |
H26 | 0.535038 | 0.360655 | 0.863168 | 0.073* | |
C27 | 0.14080 (17) | 0.81037 (18) | 0.86866 (10) | 0.0522 (3) | |
C28 | −0.0120 (2) | 0.8198 (2) | 0.86986 (16) | 0.0762 (5) | |
H28A | −0.007814 | 0.730819 | 0.907911 | 0.114* | |
H28B | −0.038814 | 0.828291 | 0.805212 | 0.114* | |
H28C | −0.085088 | 0.906099 | 0.897227 | 0.114* | |
C29 | 0.1260 (2) | 0.9610 (2) | 0.81732 (16) | 0.0788 (6) | |
H29A | 0.220344 | 0.958032 | 0.816822 | 0.118* | |
H29B | 0.053143 | 1.040075 | 0.850727 | 0.118* | |
H29C | 0.095176 | 0.979230 | 0.752289 | 0.118* | |
C30 | 0.1904 (3) | 0.7799 (3) | 0.97251 (14) | 0.0974 (8) | |
H30A | 0.281746 | 0.782916 | 0.972241 | 0.146* | |
H30B | 0.205707 | 0.682618 | 1.002855 | 0.146* | |
H30C | 0.114895 | 0.854971 | 1.007482 | 0.146* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si1 | 0.03999 (19) | 0.0469 (2) | 0.03221 (17) | −0.02263 (16) | 0.00197 (13) | −0.01050 (14) |
O1 | 0.0417 (6) | 0.0639 (7) | 0.0825 (8) | −0.0269 (5) | 0.0105 (5) | −0.0214 (6) |
O2 | 0.0513 (5) | 0.0426 (5) | 0.0349 (4) | −0.0207 (4) | −0.0033 (4) | −0.0114 (4) |
C1 | 0.0410 (7) | 0.0477 (7) | 0.0397 (6) | −0.0252 (6) | 0.0001 (5) | −0.0069 (5) |
C2 | 0.0381 (6) | 0.0373 (6) | 0.0359 (6) | −0.0189 (5) | −0.0015 (5) | −0.0096 (5) |
C3 | 0.0509 (7) | 0.0466 (7) | 0.0418 (7) | −0.0307 (6) | −0.0044 (5) | −0.0031 (5) |
C4 | 0.0608 (9) | 0.0594 (9) | 0.0695 (10) | −0.0399 (8) | −0.0159 (8) | 0.0021 (8) |
C5 | 0.0936 (14) | 0.0661 (11) | 0.1005 (15) | −0.0584 (11) | −0.0289 (11) | 0.0014 (10) |
C6 | 0.1014 (16) | 0.0496 (9) | 0.1096 (16) | −0.0451 (11) | −0.0234 (13) | −0.0081 (10) |
C7 | 0.0701 (12) | 0.0462 (9) | 0.1123 (16) | −0.0259 (8) | −0.0117 (11) | −0.0152 (9) |
C8 | 0.0550 (9) | 0.0470 (8) | 0.0814 (11) | −0.0279 (7) | −0.0079 (8) | −0.0128 (7) |
C9 | 0.0323 (6) | 0.0424 (6) | 0.0372 (6) | −0.0198 (5) | −0.0006 (4) | −0.0079 (5) |
C10 | 0.0507 (8) | 0.0439 (7) | 0.0462 (7) | −0.0240 (6) | 0.0011 (6) | −0.0102 (6) |
C11 | 0.0625 (10) | 0.0473 (8) | 0.0590 (9) | −0.0242 (7) | −0.0005 (7) | 0.0027 (7) |
C12 | 0.0610 (10) | 0.0707 (11) | 0.0418 (8) | −0.0241 (8) | 0.0020 (7) | 0.0042 (7) |
C13 | 0.0613 (9) | 0.0672 (10) | 0.0407 (7) | −0.0217 (8) | 0.0083 (6) | −0.0141 (7) |
C14 | 0.0498 (8) | 0.0476 (7) | 0.0437 (7) | −0.0191 (6) | 0.0046 (6) | −0.0128 (6) |
C15 | 0.0424 (7) | 0.0507 (7) | 0.0408 (7) | −0.0243 (6) | 0.0030 (5) | −0.0121 (6) |
C16 | 0.0498 (8) | 0.0517 (8) | 0.0435 (7) | −0.0262 (6) | 0.0040 (6) | −0.0106 (6) |
C17 | 0.0603 (10) | 0.0818 (12) | 0.0615 (10) | −0.0437 (9) | 0.0153 (8) | −0.0130 (8) |
C18 | 0.0597 (11) | 0.1225 (18) | 0.0823 (13) | −0.0603 (12) | 0.0062 (9) | −0.0188 (12) |
C19 | 0.0668 (12) | 0.149 (2) | 0.0667 (11) | −0.0673 (14) | −0.0089 (9) | −0.0136 (12) |
C20 | 0.0596 (10) | 0.1078 (15) | 0.0454 (8) | −0.0507 (10) | −0.0025 (7) | −0.0078 (9) |
C21 | 0.0597 (8) | 0.0558 (8) | 0.0322 (6) | −0.0328 (7) | −0.0008 (5) | −0.0035 (5) |
C22 | 0.0788 (12) | 0.0796 (12) | 0.0576 (9) | −0.0536 (10) | −0.0062 (8) | 0.0037 (8) |
C23 | 0.132 (2) | 0.1018 (17) | 0.0746 (13) | −0.0906 (17) | −0.0119 (13) | 0.0104 (12) |
C24 | 0.163 (3) | 0.0748 (14) | 0.0804 (15) | −0.0748 (18) | −0.0191 (16) | 0.0176 (11) |
C25 | 0.1129 (18) | 0.0577 (11) | 0.0726 (13) | −0.0308 (12) | −0.0133 (12) | 0.0099 (9) |
C26 | 0.0708 (10) | 0.0601 (9) | 0.0458 (8) | −0.0297 (8) | −0.0022 (7) | −0.0002 (7) |
C27 | 0.0490 (8) | 0.0610 (9) | 0.0424 (7) | −0.0209 (7) | 0.0063 (6) | −0.0205 (6) |
C28 | 0.0490 (9) | 0.0847 (13) | 0.0845 (13) | −0.0246 (9) | 0.0164 (9) | −0.0235 (10) |
C29 | 0.0812 (13) | 0.0592 (10) | 0.0931 (14) | −0.0285 (10) | 0.0175 (11) | −0.0334 (10) |
C30 | 0.0848 (14) | 0.1205 (19) | 0.0525 (10) | −0.0135 (13) | −0.0004 (9) | −0.0453 (11) |
Si1—O2 | 1.6534 (9) | C15—C20 | 1.396 (2) |
Si1—C15 | 1.8701 (14) | C16—C17 | 1.384 (2) |
Si1—C21 | 1.8802 (15) | C16—H16 | 0.9300 |
Si1—C27 | 1.8860 (14) | C17—C18 | 1.373 (3) |
O1—C1 | 1.2097 (17) | C17—H17 | 0.9300 |
O2—C2 | 1.4158 (14) | C18—C19 | 1.375 (3) |
C1—C3 | 1.4888 (19) | C18—H18 | 0.9300 |
C1—C2 | 1.5430 (17) | C19—C20 | 1.378 (2) |
C2—C9 | 1.5213 (17) | C19—H19 | 0.9300 |
C2—H2 | 0.9800 | C20—H20 | 0.9300 |
C3—C8 | 1.387 (2) | C21—C26 | 1.394 (2) |
C3—C4 | 1.3940 (19) | C21—C22 | 1.401 (2) |
C4—C5 | 1.380 (3) | C22—C23 | 1.388 (3) |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—C6 | 1.365 (3) | C23—C24 | 1.373 (4) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
C6—C7 | 1.371 (3) | C24—C25 | 1.372 (4) |
C6—H6 | 0.9300 | C24—H24 | 0.9300 |
C7—C8 | 1.379 (2) | C25—C26 | 1.385 (3) |
C7—H7 | 0.9300 | C25—H25 | 0.9300 |
C8—H8 | 0.9300 | C26—H26 | 0.9300 |
C9—C10 | 1.3828 (19) | C27—C28 | 1.532 (2) |
C9—C14 | 1.3911 (18) | C27—C29 | 1.535 (3) |
C10—C11 | 1.386 (2) | C27—C30 | 1.532 (2) |
C10—H10 | 0.9300 | C28—H28A | 0.9600 |
C11—C12 | 1.379 (2) | C28—H28B | 0.9600 |
C11—H11 | 0.9300 | C28—H28C | 0.9600 |
C12—C13 | 1.376 (2) | C29—H29A | 0.9600 |
C12—H12 | 0.9300 | C29—H29B | 0.9600 |
C13—C14 | 1.377 (2) | C29—H29C | 0.9600 |
C13—H13 | 0.9300 | C30—H30A | 0.9600 |
C14—H14 | 0.9300 | C30—H30B | 0.9600 |
C15—C16 | 1.3947 (19) | C30—H30C | 0.9600 |
O2—Si1—C15 | 107.79 (6) | C17—C16—H16 | 119.2 |
O2—Si1—C21 | 108.53 (6) | C15—C16—H16 | 119.2 |
C15—Si1—C21 | 110.02 (7) | C16—C17—C18 | 119.94 (16) |
O2—Si1—C27 | 104.30 (6) | C16—C17—H17 | 120.0 |
C15—Si1—C27 | 110.93 (7) | C18—C17—H17 | 120.0 |
C21—Si1—C27 | 114.88 (7) | C17—C18—C19 | 119.95 (17) |
C2—O2—Si1 | 123.85 (8) | C17—C18—H18 | 120.0 |
O1—C1—C3 | 121.75 (12) | C19—C18—H18 | 120.0 |
O1—C1—C2 | 118.40 (12) | C20—C19—C18 | 119.89 (18) |
C3—C1—C2 | 119.81 (11) | C20—C19—H19 | 120.1 |
O2—C2—C9 | 110.69 (10) | C18—C19—H19 | 120.1 |
O2—C2—C1 | 108.95 (10) | C19—C20—C15 | 121.91 (16) |
C9—C2—C1 | 107.17 (10) | C19—C20—H20 | 119.0 |
O2—C2—H2 | 110.0 | C15—C20—H20 | 119.0 |
C9—C2—H2 | 110.0 | C26—C21—C22 | 116.57 (16) |
C1—C2—H2 | 110.0 | C26—C21—Si1 | 121.98 (12) |
C8—C3—C4 | 118.63 (14) | C22—C21—Si1 | 121.23 (13) |
C8—C3—C1 | 123.36 (12) | C23—C22—C21 | 121.5 (2) |
C4—C3—C1 | 118.00 (13) | C23—C22—H22 | 119.3 |
C5—C4—C3 | 120.15 (17) | C21—C22—H22 | 119.3 |
C5—C4—H4 | 119.9 | C22—C23—C24 | 120.1 (2) |
C3—C4—H4 | 119.9 | C22—C23—H23 | 119.9 |
C4—C5—C6 | 120.32 (17) | C24—C23—H23 | 119.9 |
C4—C5—H5 | 119.8 | C25—C24—C23 | 119.8 (2) |
C6—C5—H5 | 119.8 | C25—C24—H24 | 120.1 |
C7—C6—C5 | 120.36 (17) | C23—C24—H24 | 120.1 |
C7—C6—H6 | 119.8 | C24—C25—C26 | 120.1 (2) |
C5—C6—H6 | 119.8 | C24—C25—H25 | 120.0 |
C6—C7—C8 | 120.06 (18) | C26—C25—H25 | 120.0 |
C6—C7—H7 | 120.0 | C21—C26—C25 | 121.90 (19) |
C8—C7—H7 | 120.0 | C21—C26—H26 | 119.1 |
C3—C8—C7 | 120.47 (15) | C25—C26—H26 | 119.1 |
C3—C8—H8 | 119.8 | C28—C27—C29 | 108.18 (15) |
C7—C8—H8 | 119.8 | C28—C27—C30 | 109.19 (16) |
C10—C9—C14 | 118.92 (12) | C29—C27—C30 | 109.94 (17) |
C10—C9—C2 | 121.38 (11) | C28—C27—Si1 | 111.09 (12) |
C14—C9—C2 | 119.64 (12) | C29—C27—Si1 | 107.71 (11) |
C9—C10—C11 | 120.41 (13) | C30—C27—Si1 | 110.68 (12) |
C9—C10—H10 | 119.8 | C27—C28—H28A | 109.5 |
C11—C10—H10 | 119.8 | C27—C28—H28B | 109.5 |
C12—C11—C10 | 120.08 (15) | H28A—C28—H28B | 109.5 |
C12—C11—H11 | 120.0 | C27—C28—H28C | 109.5 |
C10—C11—H11 | 120.0 | H28A—C28—H28C | 109.5 |
C13—C12—C11 | 119.78 (14) | H28B—C28—H28C | 109.5 |
C13—C12—H12 | 120.1 | C27—C29—H29A | 109.5 |
C11—C12—H12 | 120.1 | C27—C29—H29B | 109.5 |
C12—C13—C14 | 120.38 (15) | H29A—C29—H29B | 109.5 |
C12—C13—H13 | 119.8 | C27—C29—H29C | 109.5 |
C14—C13—H13 | 119.8 | H29A—C29—H29C | 109.5 |
C13—C14—C9 | 120.40 (14) | H29B—C29—H29C | 109.5 |
C13—C14—H14 | 119.8 | C27—C30—H30A | 109.5 |
C9—C14—H14 | 119.8 | C27—C30—H30B | 109.5 |
C16—C15—C20 | 116.62 (14) | H30A—C30—H30B | 109.5 |
C16—C15—Si1 | 120.66 (11) | C27—C30—H30C | 109.5 |
C20—C15—Si1 | 122.69 (11) | H30A—C30—H30C | 109.5 |
C17—C16—C15 | 121.65 (14) | H30B—C30—H30C | 109.5 |
C15—Si1—O2—C2 | 81.57 (10) | C27—Si1—C15—C16 | −113.04 (12) |
C21—Si1—O2—C2 | −37.55 (11) | O2—Si1—C15—C20 | 178.38 (14) |
C27—Si1—O2—C2 | −160.47 (10) | C21—Si1—C15—C20 | −63.45 (15) |
Si1—O2—C2—C9 | −146.22 (9) | C27—Si1—C15—C20 | 64.77 (16) |
Si1—O2—C2—C1 | 96.18 (11) | C20—C15—C16—C17 | −0.1 (2) |
O1—C1—C2—O2 | 38.34 (16) | Si1—C15—C16—C17 | 177.83 (13) |
C3—C1—C2—O2 | −143.99 (11) | C15—C16—C17—C18 | −1.3 (3) |
O1—C1—C2—C9 | −81.47 (15) | C16—C17—C18—C19 | 1.4 (3) |
C3—C1—C2—C9 | 96.20 (13) | C17—C18—C19—C20 | −0.1 (4) |
O1—C1—C3—C8 | −168.27 (15) | C18—C19—C20—C15 | −1.4 (4) |
C2—C1—C3—C8 | 14.1 (2) | C16—C15—C20—C19 | 1.5 (3) |
O1—C1—C3—C4 | 10.5 (2) | Si1—C15—C20—C19 | −176.41 (18) |
C2—C1—C3—C4 | −167.10 (13) | O2—Si1—C21—C26 | 116.05 (12) |
C8—C3—C4—C5 | −1.2 (2) | C15—Si1—C21—C26 | −1.66 (14) |
C1—C3—C4—C5 | 179.98 (16) | C27—Si1—C21—C26 | −127.68 (13) |
C3—C4—C5—C6 | 1.4 (3) | O2—Si1—C21—C22 | −58.46 (14) |
C4—C5—C6—C7 | −0.6 (4) | C15—Si1—C21—C22 | −176.18 (12) |
C5—C6—C7—C8 | −0.4 (4) | C27—Si1—C21—C22 | 57.80 (15) |
C4—C3—C8—C7 | 0.2 (3) | C26—C21—C22—C23 | −0.8 (3) |
C1—C3—C8—C7 | 178.91 (17) | Si1—C21—C22—C23 | 173.96 (15) |
C6—C7—C8—C3 | 0.7 (3) | C21—C22—C23—C24 | 0.1 (3) |
O2—C2—C9—C10 | −9.07 (16) | C22—C23—C24—C25 | 0.8 (4) |
C1—C2—C9—C10 | 109.62 (13) | C23—C24—C25—C26 | −0.9 (4) |
O2—C2—C9—C14 | 173.66 (11) | C22—C21—C26—C25 | 0.7 (2) |
C1—C2—C9—C14 | −67.66 (15) | Si1—C21—C26—C25 | −174.02 (14) |
C14—C9—C10—C11 | −1.6 (2) | C24—C25—C26—C21 | 0.1 (3) |
C2—C9—C10—C11 | −178.85 (13) | O2—Si1—C27—C28 | 59.42 (13) |
C9—C10—C11—C12 | 1.5 (2) | C15—Si1—C27—C28 | 175.21 (12) |
C10—C11—C12—C13 | −0.2 (3) | C21—Si1—C27—C28 | −59.24 (14) |
C11—C12—C13—C14 | −1.1 (3) | O2—Si1—C27—C29 | −58.89 (13) |
C12—C13—C14—C9 | 1.0 (3) | C15—Si1—C27—C29 | 56.90 (14) |
C10—C9—C14—C13 | 0.3 (2) | C21—Si1—C27—C29 | −177.55 (12) |
C2—C9—C14—C13 | 177.65 (13) | O2—Si1—C27—C30 | −179.10 (15) |
O2—Si1—C15—C16 | 0.57 (13) | C15—Si1—C27—C30 | −63.31 (17) |
C21—Si1—C15—C16 | 118.74 (12) | C21—Si1—C27—C30 | 62.24 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···O1i | 0.93 | 2.49 | 3.211 (2) | 135 |
Symmetry code: (i) x+1, y, z. |
Acknowledgements
We are grateful to the Office of the Dean at Fordham University for its generous financial support. We thank Fordham University colleagues Paul Smith and Christopher Koenigsmann for assistance in setting up the kappa-ccd system.
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