(1R,4'S)-4-(tert-Butyl-dimethyl-silan-oxy)-1-[2,2-dimethyl-3-(p-tolyl-sulfon-yl)-1,3-oxazolidin-4-yl]but-2-yn-1-ol.

The chiral title compound, C(22)H(35)NO(5)SSi, is a precursor of novel furan-omycin derivatives. It crystallizes with two molecules in the asymmetric unit; these show different conformations of the silyl substitutent, as indicated by the Si-O-C-C torsion angles of 41.4 (7) and -84.5 (5)° in the two mol-ecules. The anti configuration of the adjacent stereogenic centers is consistent with the Felkin-Anh model. Each of the two crystallographically independent mol-ecules is connected with a neighbouring mol-ecule of the same type via two symmetry-equivalent O-H⋯O hydrogen bonds.

Related literature

For related literature, see: Anh & Eisenstein (1977 ▶); Chérest et al. (1968 ▶); Deutsch et al. (2008 ▶); Erdsack & Krause (2008 ▶); Garner & Park (1987 ▶); Hoffmann-Röder & Krause (2001 ▶); Kim & Rhee (2000 ▶).

Experimental

Crystal data

C22H35NO5SSi

M = 453.66

Monoclinic,

a = 26.283 (5) Å

b = 11.335 (2) Å

c = 19.219 (4) Å

β = 121.40 (3)°

V = 4887 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 173 (1) K

0.10 × 0.08 × 0.01 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

8353 measured reflections

8353 independent reflections

3487 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.087

S = 1.03

8353 reflections

559 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 3636 Friedel pairs

Flack parameter: −0.09 (7)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014906/hb2724sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014906/hb2724Isup2.hkl

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

C22H35NO5SSi	F000 = 1952
Mr = 453.66	Dx = 1.233 Mg m−3
Monoclinic, C2	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 20719 reflections
a = 26.283 (5) Å	θ = 2.6–25.3º
b = 11.335 (2) Å	µ = 0.21 mm−1
c = 19.219 (4) Å	T = 173 (1) K
β = 121.40 (3)º	Plate, colourless
V = 4887 (2) Å3	0.10 × 0.08 × 0.01 mm
Z = 8

Nonius KappaCCD diffractometer	8353 independent reflections
Radiation source: fine-focus sealed tube	3487 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
Detector resolution: 19 vertical, 18 horizontal pixels mm-1	θmax = 25.3º
T = 173(2) K	θmin = 2.6º
286 frames via ω–rotation (Δω=1°) and two times 120 s per frame (3 sets at different κ–angles) scans	h = −31→31
Absorption correction: none	k = −12→13
8353 measured reflections	l = −23→22

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	[1.0exp(6.50(sinθ/λ)2)]/[σ2(Fo2)]
wR(F2) = 0.087	(Δ/σ)max = 0.004
S = 1.03	Δρmax = 0.18 e Å−3
8353 reflections	Δρmin = −0.20 e Å−3
559 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 3636 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.09 (7)
Secondary atom site location: difference Fourier map

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
Si	0.18831 (6)	0.75264 (12)	0.35551 (8)	0.0440 (4)
S	0.03335 (5)	0.23627 (11)	0.13817 (6)	0.0309 (3)
O1	0.02908 (13)	0.1117 (3)	0.12092 (17)	0.0387 (8)
O2	−0.01544 (11)	0.3124 (3)	0.08511 (16)	0.0360 (8)
O3	0.18264 (12)	0.2966 (3)	0.15322 (18)	0.0394 (8)
O4	0.08605 (14)	0.4847 (3)	0.03241 (17)	0.0401 (8)
H4	0.0674	0.4249	0.0053	0.048*
O5	0.15140 (15)	0.8445 (3)	0.27897 (18)	0.0514 (10)
N	0.09151 (13)	0.2865 (3)	0.13766 (19)	0.0283 (9)
C1	0.04472 (17)	0.2563 (4)	0.2366 (2)	0.0319 (11)
C2	0.03227 (18)	0.3650 (4)	0.2570 (3)	0.0344 (12)
H2B	0.0194	0.4288	0.2196	0.041*
C3	0.0387 (2)	0.3797 (4)	0.3326 (3)	0.0408 (13)
H3A	0.0301	0.4544	0.3466	0.049*
C4	0.0573 (2)	0.2888 (5)	0.3882 (3)	0.0398 (13)
C5	0.06901 (19)	0.1796 (5)	0.3667 (3)	0.0386 (13)
H5A	0.0810	0.1155	0.4038	0.046*
C6	0.06346 (17)	0.1633 (4)	0.2923 (3)	0.0330 (11)
H6A	0.0724	0.0887	0.2786	0.040*
C7	0.0632 (2)	0.3055 (5)	0.4703 (3)	0.0537 (15)
H7A	0.0324	0.2595	0.4721	0.081*
H7B	0.0584	0.3893	0.4783	0.081*
H7C	0.1027	0.2787	0.5135	0.081*
C8	0.14300 (19)	0.2100 (4)	0.1522 (3)	0.0355 (12)
C9	0.1269 (2)	0.1295 (4)	0.0813 (3)	0.0439 (13)
H9A	0.1074	0.1753	0.0306	0.066*
H9B	0.0997	0.0680	0.0785	0.066*
H9C	0.1632	0.0929	0.0886	0.066*
C10	0.17202 (19)	0.1457 (4)	0.2342 (3)	0.0408 (13)
H10A	0.1820	0.2028	0.2778	0.061*
H10B	0.2084	0.1061	0.2443	0.061*
H10C	0.1442	0.0870	0.2330	0.061*
C11	0.17841 (18)	0.3992 (4)	0.1934 (3)	0.0406 (13)
H11B	0.1911	0.4705	0.1766	0.049*
H11C	0.2037	0.3906	0.2533	0.049*
C12	0.11234 (17)	0.4078 (4)	0.1666 (3)	0.0290 (11)
H12B	0.1086	0.4258	0.2147	0.035*
C13	0.07738 (19)	0.4990 (4)	0.0990 (3)	0.0314 (11)
H13A	0.0339	0.4915	0.0789	0.038*
C14	0.0980 (2)	0.6178 (4)	0.1337 (3)	0.0372 (12)
C15	0.1154 (2)	0.7111 (5)	0.1641 (3)	0.0435 (14)
C16	0.1359 (3)	0.8307 (4)	0.1969 (3)	0.0614 (17)
H16A	0.1710	0.8504	0.1929	0.074*
H16B	0.1039	0.8877	0.1626	0.074*
C17	0.2209 (2)	0.8472 (4)	0.4478 (3)	0.0461 (13)
C18	0.2571 (2)	0.7734 (5)	0.5270 (3)	0.0722 (18)
H18A	0.2747	0.8261	0.5744	0.108*
H18B	0.2889	0.7306	0.5255	0.108*
H18C	0.2306	0.7168	0.5312	0.108*
C19	0.1699 (3)	0.9130 (6)	0.4479 (4)	0.090 (2)
H19A	0.1862	0.9621	0.4970	0.135*
H19B	0.1418	0.8558	0.4475	0.135*
H19C	0.1492	0.9632	0.3994	0.135*
C20	0.2636 (3)	0.9367 (5)	0.4439 (4)	0.089 (2)
H20A	0.2766	0.9945	0.4879	0.133*
H20B	0.2429	0.9775	0.3912	0.133*
H20C	0.2984	0.8951	0.4502	0.133*
C21	0.1340 (2)	0.6438 (5)	0.3553 (3)	0.0633 (17)
H21A	0.1090	0.6837	0.3720	0.095*
H21B	0.1560	0.5795	0.3935	0.095*
H21C	0.1087	0.6114	0.3004	0.095*
C22	0.2475 (2)	0.6744 (6)	0.3472 (3)	0.0757 (19)
H22A	0.2699	0.7317	0.3354	0.114*
H22B	0.2290	0.6161	0.3032	0.114*
H22C	0.2747	0.6344	0.3988	0.114*
S'	0.47434 (5)	0.22934 (11)	0.36956 (6)	0.0314 (3)
Si'	0.32749 (6)	0.77784 (12)	0.12641 (8)	0.0407 (4)
O1'	0.47552 (13)	0.1048 (3)	0.38495 (18)	0.0382 (8)
O2'	0.52277 (11)	0.3035 (3)	0.42724 (16)	0.0363 (8)
O3'	0.31902 (12)	0.2997 (3)	0.33146 (18)	0.0400 (8)
O4'	0.41055 (14)	0.4856 (3)	0.45876 (18)	0.0404 (8)
H4'	0.4219	0.4204	0.4830	0.048*
O5'	0.33037 (14)	0.8161 (3)	0.21186 (18)	0.0499 (10)
N'	0.41365 (13)	0.2818 (3)	0.36147 (18)	0.0270 (8)
C1'	0.47066 (16)	0.2498 (4)	0.2766 (2)	0.0290 (10)
C2'	0.48723 (19)	0.3566 (4)	0.2598 (3)	0.0375 (12)
H2'A	0.5016	0.4178	0.2994	0.045*
C3'	0.4831 (2)	0.3752 (5)	0.1858 (3)	0.0425 (13)
H3'A	0.4945	0.4492	0.1750	0.051*
C4'	0.46240 (19)	0.2872 (5)	0.1274 (3)	0.0364 (12)
C5'	0.44717 (19)	0.1792 (4)	0.1453 (3)	0.0360 (12)
H5'A	0.4342	0.1172	0.1064	0.043*
C6'	0.45037 (17)	0.1595 (4)	0.2184 (3)	0.0332 (11)
H6'A	0.4389	0.0854	0.2291	0.040*
C7'	0.4592 (2)	0.3072 (5)	0.0479 (3)	0.0486 (14)
H7'A	0.4213	0.2766	0.0031	0.073*
H7'B	0.4923	0.2660	0.0487	0.073*
H7'C	0.4619	0.3919	0.0401	0.073*
C8'	0.35917 (18)	0.2103 (4)	0.3387 (3)	0.0349 (12)
C9'	0.3689 (2)	0.1310 (4)	0.4080 (3)	0.0440 (13)
H9'A	0.3824	0.1784	0.4572	0.066*
H9'B	0.3992	0.0716	0.4183	0.066*
H9'C	0.3315	0.0915	0.3933	0.066*
C10'	0.33513 (19)	0.1429 (4)	0.2585 (3)	0.0416 (13)
H10D	0.2975	0.1045	0.2441	0.062*
H10E	0.3642	0.0830	0.2649	0.062*
H10F	0.3284	0.1981	0.2153	0.062*
C11'	0.32856 (19)	0.3992 (4)	0.2954 (3)	0.0403 (13)
H11A	0.3144	0.4719	0.3086	0.048*
H11D	0.3072	0.3904	0.2354	0.048*
C12'	0.39582 (17)	0.4040 (4)	0.3316 (3)	0.0303 (11)
H12'	0.4044	0.4206	0.2875	0.036*
C13'	0.4279 (2)	0.4945 (4)	0.4004 (2)	0.0309 (11)
H13'	0.4720	0.4833	0.4278	0.037*
C14'	0.41146 (19)	0.6151 (5)	0.3636 (3)	0.0350 (12)
C15'	0.3987 (2)	0.7067 (5)	0.3305 (3)	0.0413 (13)
C16'	0.3825 (2)	0.8229 (4)	0.2900 (3)	0.0543 (16)
H16C	0.3761	0.8795	0.3239	0.065*
H16D	0.4158	0.8528	0.2848	0.065*
C17'	0.2463 (2)	0.7598 (4)	0.0517 (3)	0.0496 (13)
C18'	0.2355 (2)	0.7335 (6)	−0.0336 (3)	0.0703 (17)
H18D	0.1930	0.7174	−0.0714	0.105*
H18E	0.2590	0.6646	−0.0308	0.105*
H18F	0.2475	0.8019	−0.0530	0.105*
C19'	0.2225 (2)	0.6565 (5)	0.0798 (4)	0.0709 (18)
H19D	0.1793	0.6491	0.0425	0.106*
H19E	0.2311	0.6722	0.1351	0.106*
H19F	0.2420	0.5830	0.0797	0.106*
C20'	0.2138 (2)	0.8750 (5)	0.0482 (4)	0.0700 (19)
H20D	0.2301	0.9405	0.0325	0.105*
H20E	0.2194	0.8910	0.1019	0.105*
H20F	0.1711	0.8667	0.0079	0.105*
C21'	0.3582 (2)	0.8992 (5)	0.0935 (3)	0.0562 (15)
H21D	0.3367	0.9725	0.0884	0.084*
H21E	0.3533	0.8791	0.0408	0.084*
H21F	0.4006	0.9096	0.1341	0.084*
C22'	0.3710 (2)	0.6407 (4)	0.1417 (3)	0.0499 (15)
H22D	0.4128	0.6541	0.1839	0.075*
H22E	0.3683	0.6191	0.0905	0.075*
H22F	0.3547	0.5767	0.1587	0.075*

	U11	U22	U33	U12	U13	U23
Si	0.0502 (8)	0.0307 (9)	0.0424 (7)	0.0001 (7)	0.0179 (6)	−0.0018 (7)
S	0.0358 (6)	0.0252 (7)	0.0308 (6)	−0.0035 (6)	0.0166 (5)	0.0012 (6)
O1	0.053 (2)	0.027 (2)	0.0371 (18)	−0.0117 (16)	0.0237 (16)	−0.0072 (15)
O2	0.0289 (16)	0.037 (2)	0.0368 (17)	0.0023 (15)	0.0131 (14)	0.0092 (16)
O3	0.0410 (18)	0.0301 (19)	0.0530 (19)	−0.0014 (16)	0.0286 (15)	−0.0008 (17)
O4	0.058 (2)	0.030 (2)	0.0303 (19)	−0.0085 (17)	0.0209 (17)	−0.0041 (15)
O5	0.078 (2)	0.029 (2)	0.037 (2)	−0.0034 (18)	0.0224 (18)	−0.0009 (15)
N	0.0334 (19)	0.022 (2)	0.0320 (19)	−0.0066 (17)	0.0192 (16)	−0.0029 (18)
C1	0.035 (2)	0.029 (3)	0.033 (2)	−0.003 (2)	0.019 (2)	0.003 (2)
C2	0.039 (3)	0.026 (3)	0.042 (3)	0.002 (2)	0.024 (2)	0.007 (2)
C3	0.054 (3)	0.028 (3)	0.048 (3)	0.005 (2)	0.031 (3)	0.000 (2)
C4	0.042 (3)	0.044 (3)	0.039 (3)	−0.003 (3)	0.024 (2)	0.001 (3)
C5	0.044 (3)	0.038 (3)	0.037 (3)	0.008 (3)	0.023 (2)	0.014 (3)
C6	0.040 (3)	0.024 (3)	0.035 (3)	0.005 (2)	0.020 (2)	0.007 (2)
C7	0.073 (4)	0.057 (4)	0.046 (3)	0.001 (3)	0.041 (3)	−0.003 (3)
C8	0.039 (3)	0.033 (3)	0.035 (3)	0.002 (2)	0.020 (2)	0.000 (2)
C9	0.056 (3)	0.036 (3)	0.046 (3)	0.008 (2)	0.031 (3)	−0.003 (3)
C10	0.044 (3)	0.032 (3)	0.044 (3)	0.004 (2)	0.021 (2)	0.004 (2)
C11	0.036 (3)	0.035 (3)	0.047 (3)	−0.005 (2)	0.019 (2)	0.002 (2)
C12	0.037 (3)	0.020 (3)	0.028 (2)	−0.007 (2)	0.015 (2)	−0.005 (2)
C13	0.035 (2)	0.020 (3)	0.035 (3)	−0.004 (2)	0.016 (2)	−0.001 (2)
C14	0.047 (3)	0.026 (3)	0.033 (3)	−0.001 (2)	0.018 (2)	0.002 (2)
C15	0.062 (3)	0.029 (3)	0.033 (3)	−0.004 (3)	0.020 (2)	0.003 (3)
C16	0.108 (5)	0.027 (3)	0.045 (3)	−0.017 (3)	0.037 (3)	−0.006 (3)
C17	0.049 (3)	0.040 (3)	0.039 (3)	−0.004 (3)	0.016 (2)	0.002 (2)
C18	0.085 (4)	0.055 (4)	0.045 (3)	0.001 (3)	0.012 (3)	0.006 (3)
C19	0.117 (5)	0.086 (5)	0.074 (4)	0.041 (4)	0.055 (4)	−0.003 (4)
C20	0.100 (5)	0.059 (5)	0.083 (5)	−0.048 (4)	0.031 (4)	−0.015 (4)
C21	0.063 (3)	0.047 (4)	0.077 (4)	−0.016 (3)	0.034 (3)	0.004 (3)
C22	0.069 (4)	0.073 (5)	0.074 (4)	0.018 (4)	0.030 (3)	−0.017 (4)
S'	0.0359 (6)	0.0280 (8)	0.0318 (6)	0.0042 (6)	0.0187 (6)	−0.0004 (6)
Si'	0.0483 (7)	0.0317 (9)	0.0401 (7)	0.0042 (7)	0.0218 (6)	0.0005 (6)
O1'	0.051 (2)	0.027 (2)	0.0393 (18)	0.0105 (16)	0.0256 (16)	0.0076 (15)
O2'	0.0321 (16)	0.042 (2)	0.0323 (16)	0.0030 (15)	0.0147 (13)	−0.0079 (16)
O3'	0.0355 (17)	0.038 (2)	0.0504 (19)	0.0021 (16)	0.0249 (15)	−0.0024 (17)
O4'	0.059 (2)	0.030 (2)	0.0347 (19)	0.0080 (17)	0.0263 (17)	0.0047 (16)
O5'	0.067 (2)	0.045 (2)	0.0360 (18)	0.0150 (18)	0.0250 (17)	0.0099 (17)
N'	0.0312 (18)	0.021 (2)	0.0297 (18)	0.0037 (17)	0.0166 (15)	0.0032 (17)
C1'	0.027 (2)	0.030 (3)	0.030 (2)	−0.002 (2)	0.0154 (18)	−0.004 (2)
C2'	0.046 (3)	0.032 (3)	0.042 (3)	−0.006 (2)	0.028 (2)	−0.009 (2)
C3'	0.060 (3)	0.031 (3)	0.050 (3)	−0.011 (3)	0.038 (3)	−0.004 (3)
C4'	0.036 (3)	0.044 (3)	0.032 (2)	−0.002 (2)	0.020 (2)	−0.001 (3)
C5'	0.044 (3)	0.031 (3)	0.033 (3)	−0.003 (2)	0.020 (2)	−0.007 (2)
C6'	0.036 (2)	0.024 (3)	0.039 (3)	−0.005 (2)	0.019 (2)	−0.004 (2)
C7'	0.057 (3)	0.057 (4)	0.043 (3)	−0.001 (3)	0.034 (2)	0.001 (3)
C8'	0.034 (2)	0.032 (3)	0.043 (3)	0.001 (2)	0.023 (2)	0.001 (2)
C9'	0.053 (3)	0.040 (3)	0.049 (3)	−0.010 (2)	0.033 (3)	0.003 (3)
C10'	0.046 (3)	0.035 (3)	0.044 (3)	−0.007 (2)	0.023 (2)	−0.008 (2)
C11'	0.043 (3)	0.029 (3)	0.044 (3)	0.005 (2)	0.020 (2)	−0.001 (2)
C12'	0.033 (2)	0.026 (3)	0.031 (3)	0.008 (2)	0.016 (2)	−0.001 (2)
C13'	0.044 (3)	0.022 (3)	0.026 (3)	0.005 (2)	0.018 (2)	0.005 (2)
C14'	0.036 (3)	0.036 (3)	0.033 (3)	0.000 (2)	0.018 (2)	−0.006 (3)
C15'	0.056 (3)	0.031 (3)	0.035 (3)	−0.002 (2)	0.022 (2)	−0.001 (2)
C16'	0.083 (4)	0.025 (3)	0.039 (3)	−0.003 (3)	0.020 (3)	−0.002 (2)
C17'	0.057 (3)	0.039 (3)	0.058 (3)	−0.003 (3)	0.033 (2)	0.003 (3)
C18'	0.066 (3)	0.091 (5)	0.046 (3)	−0.020 (4)	0.023 (3)	−0.008 (4)
C19'	0.075 (4)	0.055 (4)	0.101 (5)	−0.026 (3)	0.058 (4)	−0.011 (4)
C20'	0.053 (3)	0.061 (5)	0.090 (5)	0.010 (3)	0.033 (3)	0.006 (3)
C21'	0.059 (3)	0.041 (3)	0.077 (4)	−0.007 (3)	0.042 (3)	0.000 (3)
C22'	0.059 (3)	0.034 (3)	0.058 (3)	0.016 (3)	0.031 (3)	0.003 (3)

Si—O5	1.644 (3)	S'—O1'	1.439 (3)
Si—C17	1.856 (5)	S'—O2'	1.444 (3)
Si—C22	1.868 (5)	S'—N'	1.632 (3)
Si—C21	1.887 (5)	S'—C1'	1.754 (4)
S—O2	1.437 (3)	Si'—O5'	1.662 (3)
S—O1	1.442 (3)	Si'—C22'	1.859 (5)
S—N	1.636 (3)	Si'—C17'	1.861 (4)
S—C1	1.769 (4)	Si'—C21'	1.863 (5)
O3—C8	1.424 (5)	O3'—C11'	1.413 (6)
O3—C11	1.432 (6)	O3'—C8'	1.416 (5)
O4—C13	1.421 (5)	O4'—C13'	1.418 (5)
O4—H4	0.8400	O4'—H4'	0.8400
O5—C16	1.417 (6)	O5'—C16'	1.412 (5)
N—C12	1.478 (5)	N'—C12'	1.479 (5)
N—C8	1.506 (6)	N'—C8'	1.499 (5)
C1—C2	1.383 (6)	C1'—C2'	1.380 (6)
C1—C6	1.397 (6)	C1'—C6'	1.400 (6)
C2—C3	1.381 (6)	C2'—C3'	1.385 (7)
C2—H2B	0.9500	C2'—H2'A	0.9500
C3—C4	1.378 (7)	C3'—C4'	1.384 (7)
C3—H3A	0.9500	C3'—H3'A	0.9500
C4—C5	1.389 (7)	C4'—C5'	1.386 (6)
C4—C7	1.514 (6)	C4'—C7'	1.502 (6)
C5—C6	1.373 (6)	C5'—C6'	1.380 (6)
C5—H5A	0.9500	C5'—H5'A	0.9500
C6—H6A	0.9500	C6'—H6'A	0.9500
C7—H7A	0.9800	C7'—H7'A	0.9800
C7—H7B	0.9800	C7'—H7'B	0.9800
C7—H7C	0.9800	C7'—H7'C	0.9800
C8—C9	1.506 (6)	C8'—C9'	1.514 (6)
C8—C10	1.532 (6)	C8'—C10'	1.531 (6)
C9—H9A	0.9800	C9'—H9'A	0.9800
C9—H9B	0.9800	C9'—H9'B	0.9800
C9—H9C	0.9800	C9'—H9'C	0.9800
C10—H10A	0.9800	C10'—H10D	0.9800
C10—H10B	0.9800	C10'—H10E	0.9800
C10—H10C	0.9800	C10'—H10F	0.9800
C11—C12	1.536 (6)	C11'—C12'	1.527 (6)
C11—H11B	0.9900	C11'—H11A	0.9900
C11—H11C	0.9900	C11'—H11D	0.9900
C12—C13	1.535 (6)	C12'—C13'	1.533 (6)
C12—H12B	1.0000	C12'—H12'	1.0000
C13—C14	1.476 (7)	C13'—C14'	1.495 (7)
C13—H13A	1.0000	C13'—H13'	1.0000
C14—C15	1.179 (6)	C14'—C15'	1.171 (6)
C15—C16	1.474 (7)	C15'—C16'	1.477 (7)
C16—H16A	0.9900	C16'—H16C	0.9900
C16—H16B	0.9900	C16'—H16D	0.9900
C17—C19	1.533 (7)	C17'—C18'	1.541 (7)
C17—C20	1.543 (7)	C17'—C20'	1.543 (7)
C17—C18	1.555 (6)	C17'—C19'	1.551 (7)
C18—H18A	0.9800	C18'—H18D	0.9800
C18—H18B	0.9800	C18'—H18E	0.9800
C18—H18C	0.9800	C18'—H18F	0.9800
C19—H19A	0.9800	C19'—H19D	0.9800
C19—H19B	0.9800	C19'—H19E	0.9800
C19—H19C	0.9800	C19'—H19F	0.9800
C20—H20A	0.9800	C20'—H20D	0.9800
C20—H20B	0.9800	C20'—H20E	0.9800
C20—H20C	0.9800	C20'—H20F	0.9800
C21—H21A	0.9800	C21'—H21D	0.9800
C21—H21B	0.9800	C21'—H21E	0.9800
C21—H21C	0.9800	C21'—H21F	0.9800
C22—H22A	0.9800	C22'—H22D	0.9800
C22—H22B	0.9800	C22'—H22E	0.9800
C22—H22C	0.9800	C22'—H22F	0.9800
O5—Si—C17	104.6 (2)	O1'—S'—O2'	119.81 (19)
O5—Si—C22	110.7 (3)	O1'—S'—N'	107.00 (19)
C17—Si—C22	111.5 (2)	O2'—S'—N'	106.73 (18)
O5—Si—C21	108.6 (2)	O1'—S'—C1'	108.8 (2)
C17—Si—C21	110.6 (3)	O2'—S'—C1'	105.3 (2)
C22—Si—C21	110.7 (3)	N'—S'—C1'	108.81 (18)
O2—S—O1	119.40 (18)	O5'—Si'—C22'	110.7 (2)
O2—S—N	106.14 (19)	O5'—Si'—C17'	103.6 (2)
O1—S—N	107.5 (2)	C22'—Si'—C17'	113.2 (2)
O2—S—C1	105.8 (2)	O5'—Si'—C21'	109.7 (2)
O1—S—C1	108.8 (2)	C22'—Si'—C21'	109.4 (2)
N—S—C1	108.89 (18)	C17'—Si'—C21'	110.1 (2)
C8—O3—C11	107.8 (3)	C11'—O3'—C8'	107.8 (3)
C13—O4—H4	109.5	C13'—O4'—H4'	109.5
C16—O5—Si	128.3 (3)	C16'—O5'—Si'	125.7 (3)
C12—N—C8	110.2 (3)	C12'—N'—C8'	109.4 (3)
C12—N—S	119.0 (3)	C12'—N'—S'	118.3 (3)
C8—N—S	123.4 (3)	C8'—N'—S'	124.6 (3)
C2—C1—C6	119.7 (4)	C2'—C1'—C6'	119.4 (4)
C2—C1—S	119.0 (3)	C2'—C1'—S'	119.8 (3)
C6—C1—S	121.2 (4)	C6'—C1'—S'	120.9 (4)
C3—C2—C1	119.2 (4)	C1'—C2'—C3'	120.5 (4)
C3—C2—H2B	120.4	C1'—C2'—H2'A	119.7
C1—C2—H2B	120.4	C3'—C2'—H2'A	119.7
C4—C3—C2	121.7 (5)	C4'—C3'—C2'	120.7 (5)
C4—C3—H3A	119.2	C4'—C3'—H3'A	119.7
C2—C3—H3A	119.2	C2'—C3'—H3'A	119.7
C3—C4—C5	118.6 (5)	C3'—C4'—C5'	118.5 (4)
C3—C4—C7	121.1 (5)	C3'—C4'—C7'	120.4 (5)
C5—C4—C7	120.3 (4)	C5'—C4'—C7'	121.0 (4)
C6—C5—C4	120.7 (5)	C6'—C5'—C4'	121.5 (5)
C6—C5—H5A	119.7	C6'—C5'—H5'A	119.2
C4—C5—H5A	119.7	C4'—C5'—H5'A	119.2
C5—C6—C1	120.0 (5)	C5'—C6'—C1'	119.3 (5)
C5—C6—H6A	120.0	C5'—C6'—H6'A	120.3
C1—C6—H6A	120.0	C1'—C6'—H6'A	120.3
C4—C7—H7A	109.5	C4'—C7'—H7'A	109.5
C4—C7—H7B	109.5	C4'—C7'—H7'B	109.5
H7A—C7—H7B	109.5	H7'A—C7'—H7'B	109.5
C4—C7—H7C	109.5	C4'—C7'—H7'C	109.5
H7A—C7—H7C	109.5	H7'A—C7'—H7'C	109.5
H7B—C7—H7C	109.5	H7'B—C7'—H7'C	109.5
O3—C8—N	100.7 (4)	O3'—C8'—N'	101.0 (4)
O3—C8—C9	106.8 (4)	O3'—C8'—C9'	106.7 (4)
N—C8—C9	112.3 (3)	N'—C8'—C9'	111.5 (3)
O3—C8—C10	110.2 (3)	O3'—C8'—C10'	111.2 (3)
N—C8—C10	112.5 (4)	N'—C8'—C10'	113.2 (4)
C9—C8—C10	113.4 (4)	C9'—C8'—C10'	112.4 (4)
C8—C9—H9A	109.5	C8'—C9'—H9'A	109.5
C8—C9—H9B	109.5	C8'—C9'—H9'B	109.5
H9A—C9—H9B	109.5	H9'A—C9'—H9'B	109.5
C8—C9—H9C	109.5	C8'—C9'—H9'C	109.5
H9A—C9—H9C	109.5	H9'A—C9'—H9'C	109.5
H9B—C9—H9C	109.5	H9'B—C9'—H9'C	109.5
C8—C10—H10A	109.5	C8'—C10'—H10D	109.5
C8—C10—H10B	109.5	C8'—C10'—H10E	109.5
H10A—C10—H10B	109.5	H10D—C10'—H10E	109.5
C8—C10—H10C	109.5	C8'—C10'—H10F	109.5
H10A—C10—H10C	109.5	H10D—C10'—H10F	109.5
H10B—C10—H10C	109.5	H10E—C10'—H10F	109.5
O3—C11—C12	105.3 (3)	O3'—C11'—C12'	105.3 (4)
O3—C11—H11B	110.7	O3'—C11'—H11A	110.7
C12—C11—H11B	110.7	C12'—C11'—H11A	110.7
O3—C11—H11C	110.7	O3'—C11'—H11D	110.7
C12—C11—H11C	110.7	C12'—C11'—H11D	110.7
H11B—C11—H11C	108.8	H11A—C11'—H11D	108.8
N—C12—C13	111.5 (3)	N'—C12'—C11'	101.6 (4)
N—C12—C11	101.5 (4)	N'—C12'—C13'	111.8 (3)
C13—C12—C11	113.6 (4)	C11'—C12'—C13'	113.7 (4)
N—C12—H12B	110.0	N'—C12'—H12'	109.8
C13—C12—H12B	110.0	C11'—C12'—H12'	109.8
C11—C12—H12B	110.0	C13'—C12'—H12'	109.8
O4—C13—C14	108.5 (4)	O4'—C13'—C14'	107.9 (4)
O4—C13—C12	112.3 (4)	O4'—C13'—C12'	112.0 (4)
C14—C13—C12	108.3 (3)	C14'—C13'—C12'	108.1 (3)
O4—C13—H13A	109.2	O4'—C13'—H13'	109.6
C14—C13—H13A	109.2	C14'—C13'—H13'	109.6
C12—C13—H13A	109.2	C12'—C13'—H13'	109.6
C15—C14—C13	177.7 (5)	C15'—C14'—C13'	175.6 (5)
C14—C15—C16	176.4 (5)	C14'—C15'—C16'	179.0 (6)
O5—C16—C15	114.0 (4)	O5'—C16'—C15'	111.4 (4)
O5—C16—H16A	108.8	O5'—C16'—H16C	109.3
C15—C16—H16A	108.8	C15'—C16'—H16C	109.3
O5—C16—H16B	108.8	O5'—C16'—H16D	109.3
C15—C16—H16B	108.8	C15'—C16'—H16D	109.3
H16A—C16—H16B	107.7	H16C—C16'—H16D	108.0
C19—C17—C20	109.7 (5)	C18'—C17'—C20'	109.0 (4)
C19—C17—C18	110.5 (5)	C18'—C17'—C19'	109.9 (4)
C20—C17—C18	108.1 (4)	C20'—C17'—C19'	109.8 (4)
C19—C17—Si	108.3 (3)	C18'—C17'—Si'	110.1 (3)
C20—C17—Si	108.6 (4)	C20'—C17'—Si'	109.1 (3)
C18—C17—Si	111.5 (4)	C19'—C17'—Si'	108.8 (3)
C17—C18—H18A	109.5	C17'—C18'—H18D	109.5
C17—C18—H18B	109.5	C17'—C18'—H18E	109.5
H18A—C18—H18B	109.5	H18D—C18'—H18E	109.5
C17—C18—H18C	109.5	C17'—C18'—H18F	109.5
H18A—C18—H18C	109.5	H18D—C18'—H18F	109.5
H18B—C18—H18C	109.5	H18E—C18'—H18F	109.5
C17—C19—H19A	109.5	C17'—C19'—H19D	109.5
C17—C19—H19B	109.5	C17'—C19'—H19E	109.5
H19A—C19—H19B	109.5	H19D—C19'—H19E	109.5
C17—C19—H19C	109.5	C17'—C19'—H19F	109.5
H19A—C19—H19C	109.5	H19D—C19'—H19F	109.5
H19B—C19—H19C	109.5	H19E—C19'—H19F	109.5
C17—C20—H20A	109.5	C17'—C20'—H20D	109.5
C17—C20—H20B	109.5	C17'—C20'—H20E	109.5
H20A—C20—H20B	109.5	H20D—C20'—H20E	109.5
C17—C20—H20C	109.5	C17'—C20'—H20F	109.5
H20A—C20—H20C	109.5	H20D—C20'—H20F	109.5
H20B—C20—H20C	109.5	H20E—C20'—H20F	109.5
Si—C21—H21A	109.5	Si'—C21'—H21D	109.5
Si—C21—H21B	109.5	Si'—C21'—H21E	109.5
H21A—C21—H21B	109.5	H21D—C21'—H21E	109.5
Si—C21—H21C	109.5	Si'—C21'—H21F	109.5
H21A—C21—H21C	109.5	H21D—C21'—H21F	109.5
H21B—C21—H21C	109.5	H21E—C21'—H21F	109.5
Si—C22—H22A	109.5	Si'—C22'—H22D	109.5
Si—C22—H22B	109.5	Si'—C22'—H22E	109.5
H22A—C22—H22B	109.5	H22D—C22'—H22E	109.5
Si—C22—H22C	109.5	Si'—C22'—H22F	109.5
H22A—C22—H22C	109.5	H22D—C22'—H22F	109.5
H22B—C22—H22C	109.5	H22E—C22'—H22F	109.5
C17—Si—O5—C16	155.8 (4)	C17'—Si'—O5'—C16'	169.9 (4)
C22—Si—O5—C16	35.6 (5)	C21'—Si'—O5'—C16'	−72.6 (4)
C21—Si—O5—C16	−86.1 (5)	O1'—S'—N'—C12'	−169.6 (3)
O2—S—N—C12	61.0 (3)	O2'—S'—N'—C12'	61.0 (3)
O1—S—N—C12	−170.2 (3)	C1'—S'—N'—C12'	−52.2 (3)
C1—S—N—C12	−52.6 (3)	O1'—S'—N'—C8'	−23.5 (4)
O2—S—N—C8	−151.9 (3)	O2'—S'—N'—C8'	−152.9 (3)
O1—S—N—C8	−23.1 (3)	C1'—S'—N'—C8'	94.0 (4)
C1—S—N—C8	94.6 (3)	O1'—S'—C1'—C2'	−160.1 (3)
O2—S—C1—C2	−31.0 (4)	O2'—S'—C1'—C2'	−30.4 (4)
O1—S—C1—C2	−160.4 (3)	N'—S'—C1'—C2'	83.7 (4)
N—S—C1—C2	82.7 (4)	O1'—S'—C1'—C6'	20.7 (4)
O2—S—C1—C6	146.2 (3)	O2'—S'—C1'—C6'	150.4 (3)
O1—S—C1—C6	16.7 (4)	N'—S'—C1'—C6'	−95.5 (4)
N—S—C1—C6	−100.1 (4)	C6'—C1'—C2'—C3'	0.9 (7)
C6—C1—C2—C3	0.1 (6)	S'—C1'—C2'—C3'	−178.3 (4)
S—C1—C2—C3	177.3 (4)	C1'—C2'—C3'—C4'	−0.2 (7)
C1—C2—C3—C4	0.0 (7)	C2'—C3'—C4'—C5'	−1.3 (7)
C2—C3—C4—C5	−0.8 (7)	C2'—C3'—C4'—C7'	−178.8 (4)
C2—C3—C4—C7	−179.0 (4)	C3'—C4'—C5'—C6'	2.1 (7)
C3—C4—C5—C6	1.5 (7)	C7'—C4'—C5'—C6'	179.5 (4)
C7—C4—C5—C6	179.6 (4)	C4'—C5'—C6'—C1'	−1.4 (7)
C4—C5—C6—C1	−1.3 (7)	C2'—C1'—C6'—C5'	−0.2 (7)
C2—C1—C6—C5	0.5 (6)	S'—C1'—C6'—C5'	179.0 (3)
S—C1—C6—C5	−176.7 (3)	C11'—O3'—C8'—N'	38.2 (4)
C11—O3—C8—N	37.8 (4)	C11'—O3'—C8'—C9'	154.9 (4)
C11—O3—C8—C9	155.2 (4)	C11'—O3'—C8'—C10'	−82.2 (4)
C11—O3—C8—C10	−81.2 (4)	C12'—N'—C8'—O3'	−24.8 (4)
C12—N—C8—O3	−25.0 (4)	S'—N'—C8'—O3'	−173.5 (3)
S—N—C8—O3	−174.6 (3)	C12'—N'—C8'—C9'	−137.9 (4)
C12—N—C8—C9	−138.3 (4)	S'—N'—C8'—C9'	73.4 (5)
S—N—C8—C9	72.1 (5)	C12'—N'—C8'—C10'	94.3 (4)
C12—N—C8—C10	92.3 (4)	S'—N'—C8'—C10'	−54.4 (5)
S—N—C8—C10	−57.3 (4)	C8'—O3'—C11'—C12'	−37.7 (5)
C8—O3—C11—C12	−37.1 (5)	C8'—N'—C12'—C11'	3.4 (4)
C8—N—C12—C13	125.1 (4)	S'—N'—C12'—C11'	154.4 (3)
S—N—C12—C13	−83.8 (4)	C8'—N'—C12'—C13'	125.0 (4)
C8—N—C12—C11	3.8 (4)	S'—N'—C12'—C13'	−84.0 (4)
S—N—C12—C11	155.0 (3)	O3'—C11'—C12'—N'	19.6 (5)
O3—C11—C12—N	19.0 (4)	O3'—C11'—C12'—C13'	−100.6 (4)
O3—C11—C12—C13	−100.8 (4)	N'—C12'—C13'—O4'	−66.3 (5)
N—C12—C13—O4	−63.6 (5)	C11'—C12'—C13'—O4'	48.0 (5)
C11—C12—C13—O4	50.3 (5)	N'—C12'—C13'—C14'	175.0 (4)
N—C12—C13—C14	176.6 (4)	C11'—C12'—C13'—C14'	−70.7 (5)
C11—C12—C13—C14	−69.5 (5)	Si'—O5'—C16'—C15'	−84.5 (5)
O5—Si—C17—C19	57.4 (4)	O5'—Si'—C17'—C18'	175.5 (4)
C22—Si—C17—C19	177.1 (4)	C22'—Si'—C17'—C18'	−64.5 (4)
C21—Si—C17—C19	−59.3 (4)	C21'—Si'—C17'—C18'	58.2 (5)
O5—Si—C17—C20	−61.7 (4)	O5'—Si'—C17'—C20'	55.9 (4)
C22—Si—C17—C20	58.0 (4)	C22'—Si'—C17'—C20'	175.8 (4)
C21—Si—C17—C20	−178.5 (4)	C21'—Si'—C17'—C20'	−61.4 (4)
O5—Si—C17—C18	179.2 (4)	O5'—Si'—C17'—C19'	−63.9 (4)
C22—Si—C17—C18	−61.1 (5)	C22'—Si'—C17'—C19'	56.0 (4)
C21—Si—C17—C18	62.5 (4)	C21'—Si'—C17'—C19'	178.8 (4)
C22'—Si'—O5'—C16'	48.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2i	0.84	2.01	2.828 (4)	164
O4'—H4'···O2'ii	0.84	2.06	2.851 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2i	0.84	2.01	2.828 (4)	164
O4′—H4′⋯O2′ii	0.84	2.06	2.851 (4)	157

Symmetry codes: (i) ; (ii) .