Crystal chemistry of trialkylsilyl-capped (3Z)-4-(methylthio)-3-penten-1-yne: polymorphism, twinning and ambiguity of order–disorder descriptions

Lumpi, D.; Kautny, P.; Stöger, B.; Fröhlich, J.

doi:10.1107/S2052520616010969

Crystal chemistry of trialkylsilyl-capped (3Z)-4-(methylthio)-3-penten-1-yne: polymorphism, twinning and ambiguity of order–disorder descriptions

D. Lumpi, P. Kautny, B. Stöger and J. Fröhlich

The crystallization behavior of trimethylsilyl-capped (3Z)-4-(methylthio)-3-penten-1-yne (1-TMS) and the triisopropylsilyl and tert-butyldimethylsilyl analogues (1-TIPS) and (1-TBDMS) was investigated. (1-TMS) crystallizes in the Sohncke space group P2₁2₁2₁ with Z′ = 1. (1-TIPS) exists as two polymorphs, both crystallizing in $P\overline 1$ with Z′ = 2 independent molecules. Polymorph (I) is an order–disorder (OD) twin. Two interpretations in terms of M = 1 or M = 2 kinds of OD layers are possible, with different degrees of idealization. Polymorph (II) is fully ordered (non-twinned). Its structure can be derived from polymorph (I) by inverting the orientation of every second molecule. (1-TBDMS) ( $P\overline1$ , Z′ = 2) is an OD twin, where the OD description is unambiguously in M = 1 kinds of layers.

Keywords: layer structures; twinning; order–disorder theory; desymmetrization; polymorphism; Hirshfeld fingerprint plots.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520616010969/ps5052sup1.cif Contains datablocks Z_TMS, Z_TIPS_1, Z_TIPS_2, Z_TBDMS
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520616010969/ps5052Z_TMSsup2.hkl Contains datablock Z_TMS
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520616010969/ps5052Z_TIPS_1sup3.hkl Contains datablock Z_TIPS_1
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520616010969/ps5052Z_TIPS_2sup4.hkl Contains datablock Z_TIPS_2
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520616010969/ps5052Z_TBDMSsup5.hkl Contains datablock Z_TBDMS

CCDC references: 1491092; 1491093; 1491094; 1491095

Computing details top

(Z_TMS) top

Crystal data top

C₉H₁₆SSi	F(000) = 400
M_r = 184.4	D_x = 1.106 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2xab;2ybc;2zac	Cell parameters from 9994 reflections
a = 5.6366 (4) Å	θ = 2.3–30.0°
b = 11.0112 (8) Å	µ = 0.35 mm⁻¹
c = 17.8309 (14) Å	T = 100 K
V = 1106.69 (14) Å³	Plate, translucent colourless
Z = 4	0.52 × 0.46 × 0.07 mm

Data collection top

Bruker KAPPA APEX II CCD diffractometer	3254 independent reflections
Radiation source: X-ray tube	2933 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.040
ω– and φ–scans	θ_max = 30.1°, θ_min = 2.2°
Absorption correction: multi-scan SADABS	h = −7→7
T_min = 0.84, T_max = 0.98	k = −15→15
38182 measured reflections	l = −25→25

Refinement top

Refinement on F	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.025	Weighting scheme based on measured s.u.'s w = 1/(σ²(F) + 0.0001F²)
wR(F²) = 0.028	(Δ/σ)_max = 0.017
S = 1.52	Δρ_max = 0.20 e Å⁻³
3254 reflections	Δρ_min = −0.15 e Å⁻³
101 parameters	Absolute structure: 1894 of Friedel pairs used in the refinement
0 restraints	Absolute structure parameter: 0.42 (6)
64 constraints

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

	x	y	z	U_iso*/U_eq
Si1	0.98990 (6)	−0.02554 (3)	1.168225 (16)	0.01605 (8)
S1	0.38834 (6)	0.10725 (3)	0.948364 (18)	0.02382 (8)
C1	0.1672 (2)	−0.10125 (11)	0.89055 (6)	0.0221 (3)
C2	0.35155 (19)	−0.05044 (9)	0.94238 (6)	0.0158 (3)
C3	0.4964 (2)	−0.12187 (10)	0.98250 (6)	0.0187 (3)
C4	0.6658 (2)	−0.08006 (10)	1.03625 (6)	0.0183 (3)
C5	0.8048 (2)	−0.05183 (10)	1.08454 (6)	0.0182 (3)
C6	1.1716 (2)	0.11360 (11)	1.15614 (7)	0.0264 (4)
C7	1.1814 (2)	−0.16148 (11)	1.18122 (7)	0.0279 (4)
C8	0.7861 (2)	−0.00952 (14)	1.24955 (7)	0.0306 (4)
C9	0.1116 (3)	0.16835 (12)	0.91647 (8)	0.0358 (4)
H11	0.190716	−0.069062	0.841069	0.0265*
H12	0.180628	−0.18813	0.889164	0.0265*
H13	0.012292	−0.079083	0.908227	0.0265*
H31	0.485443	−0.207902	0.974498	0.0224*
H61	1.269076	0.125349	1.199686	0.0317*
H62	1.270624	0.105007	1.11267	0.0317*
H63	1.068997	0.182447	1.149824	0.0317*
H71	1.262127	−0.155937	1.228511	0.0335*
H72	1.085073	−0.233357	1.180434	0.0335*
H73	1.295917	−0.165297	1.141435	0.0335*
H81	0.877144	−0.003309	1.294888	0.0368*
H82	0.691507	0.062314	1.243469	0.0368*
H83	0.684327	−0.079288	1.252308	0.0368*
H91	0.117803	0.255434	0.918207	0.0429*
H92	0.082934	0.142434	0.865873	0.0429*
H93	−0.014171	0.139938	0.948245	0.0429*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.01340 (13)	0.02014 (14)	0.01461 (13)	−0.00062 (13)	−0.00145 (13)	0.00132 (12)
S1	0.02657 (15)	0.01739 (13)	0.02748 (16)	0.00082 (13)	−0.00728 (13)	0.00072 (12)
C1	0.0212 (6)	0.0258 (6)	0.0192 (6)	−0.0031 (5)	−0.0054 (5)	−0.0002 (5)
C2	0.0160 (5)	0.0182 (5)	0.0131 (5)	−0.0018 (4)	0.0003 (4)	−0.0020 (4)
C3	0.0213 (5)	0.0165 (5)	0.0184 (5)	−0.0002 (5)	−0.0028 (5)	−0.0010 (4)
C4	0.0192 (6)	0.0166 (5)	0.0189 (6)	0.0021 (4)	0.0007 (4)	0.0029 (4)
C5	0.0184 (5)	0.0187 (5)	0.0175 (5)	0.0016 (4)	0.0007 (4)	0.0009 (4)
C6	0.0275 (7)	0.0250 (6)	0.0268 (7)	−0.0061 (5)	−0.0043 (5)	0.0054 (5)
C7	0.0251 (7)	0.0256 (6)	0.0331 (8)	0.0024 (5)	−0.0087 (6)	0.0046 (5)
C8	0.0196 (6)	0.0531 (9)	0.0193 (6)	−0.0051 (6)	0.0011 (5)	−0.0061 (6)
C9	0.0359 (8)	0.0321 (7)	0.0393 (8)	0.0164 (7)	−0.0089 (7)	−0.0074 (6)

Geometric parameters (Å, º) top

Si1—C5	1.8435 (12)	C6—H61	0.96
Si1—C6	1.8553 (13)	C6—H62	0.96
Si1—C7	1.8600 (13)	C6—H63	0.96
Si1—C8	1.8584 (13)	C7—H71	0.96
S1—C2	1.7519 (11)	C7—H72	0.96
C1—C2	1.4988 (16)	C7—H73	0.96
C1—H11	0.96	C8—H81	0.96
C1—H12	0.96	C8—H82	0.96
C1—H13	0.96	C8—H83	0.96
C2—C3	1.3405 (15)	C9—H91	0.96
C3—C4	1.4291 (16)	C9—H92	0.96
C3—H31	0.96	C9—H93	0.96
C4—C5	1.2052 (16)

C5—Si1—C6	110.37 (5)	Si1—C6—H62	109.47
C5—Si1—C7	107.63 (5)	Si1—C6—H63	109.47
C5—Si1—C8	107.26 (6)	H61—C6—H62	109.47
C6—Si1—C7	111.02 (6)	H61—C6—H63	109.47
C6—Si1—C8	110.69 (6)	H62—C6—H63	109.47
C7—Si1—C8	109.75 (6)	Si1—C7—H71	109.47
C2—C1—H11	109.47	Si1—C7—H72	109.47
C2—C1—H12	109.47	Si1—C7—H73	109.47
C2—C1—H13	109.47	H71—C7—H72	109.47
H11—C1—H12	109.47	H71—C7—H73	109.47
H11—C1—H13	109.47	H72—C7—H73	109.47
H12—C1—H13	109.47	Si1—C8—H81	109.47
S1—C2—C1	119.31 (8)	Si1—C8—H82	109.47
S1—C2—C3	118.48 (8)	Si1—C8—H83	109.47
C1—C2—C3	122.16 (10)	H81—C8—H82	109.47
C2—C3—C4	125.16 (10)	H81—C8—H83	109.47
C2—C3—H31	117.42	H82—C8—H83	109.47
C4—C3—H31	117.42	H91—C9—H92	109.47
C3—C4—C5	175.43 (12)	H91—C9—H93	109.47
Si1—C5—C4	170.70 (10)	H92—C9—H93	109.47
Si1—C6—H61	109.47

(Z_TIPS_1) top

Crystal data top

C₁₅H₂₈SSi	Z = 4
M_r = 268.5	F(000) = 592
Triclinic, P1	D_x = 1.071 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 7.962 (2) Å	Cell parameters from 3567 reflections
b = 13.842 (3) Å	θ = 2.7–25.7°
c = 15.326 (3) Å	µ = 0.25 mm⁻¹
α = 92.330 (6)°	T = 100 K
β = 99.313 (10)°	Plate, translucent colourless
γ = 90.721 (11)°	0.55 × 0.25 × 0.02 mm
V = 1665.1 (7) Å³

Data collection top

Bruker KAPPA APEX II CCD diffractometer	4002 independent reflections
Radiation source: X-ray tube	2725 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.042
ω– and φ–scans	θ_max = 27.9°, θ_min = 1.4°
Absorption correction: multi-scan SADABS	h = −9→9
T_min = 0.93, T_max = 1.00	k = −16→17
17126 measured reflections	l = 0→19

Refinement top

Refinement on F	224 constraints
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.054	Weighting scheme based on measured s.u.'s w = 1/(σ²(F) + 0.0001F²)
S = 1.74	(Δ/σ)_max = 0.023
4002 reflections	Δρ_max = 0.36 e Å⁻³
308 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints

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

	x	y	z	U_iso*/U_eq
Si1	1.4720 (2)	0.06204 (10)	−0.19979 (7)	0.0223 (6)
S1	0.8968 (2)	0.12480 (11)	−0.40356 (7)	0.0291 (6)
C1	1.3115 (7)	0.0172 (3)	−0.1317 (3)	0.024 (2)
C2	1.1828 (7)	0.0937 (4)	−0.1177 (3)	0.035 (2)
C3	1.2192 (8)	−0.0759 (4)	−0.1709 (3)	0.038 (2)
C4	1.5725 (7)	0.1796 (3)	−0.1501 (2)	0.030 (2)
C5	1.7064 (7)	0.2188 (3)	−0.1999 (3)	0.032 (2)
C6	1.6459 (8)	0.1760 (4)	−0.0511 (3)	0.042 (3)
C7	1.6361 (7)	−0.0287 (3)	−0.2168 (3)	0.029 (2)
C8	1.5854 (8)	−0.1048 (3)	−0.2921 (3)	0.040 (2)
C9	1.7041 (8)	−0.0771 (4)	−0.1305 (3)	0.039 (3)
C10	1.3545 (7)	0.0905 (3)	−0.3089 (3)	0.020 (2)
C11	1.2797 (7)	0.1083 (4)	−0.3804 (3)	0.018 (2)
C12	1.1916 (8)	0.1255 (3)	−0.4664 (3)	0.019 (2)
C13	1.0229 (8)	0.1307 (3)	−0.4878 (3)	0.019 (2)
C14	0.9366 (7)	0.1435 (3)	−0.5811 (2)	0.024 (2)
C15	0.6805 (8)	0.1118 (4)	−0.4621 (3)	0.027 (2)
Si2	0.2547 (2)	0.55538 (9)	−0.20224 (7)	0.0191 (6)
S2	0.6745 (2)	0.63233 (10)	−0.41946 (7)	0.0253 (6)
C16	0.4631 (7)	0.5544 (3)	−0.1294 (3)	0.025 (2)
C17	0.5541 (8)	0.6536 (4)	−0.1184 (3)	0.040 (3)
C18	0.5817 (7)	0.4777 (3)	−0.1594 (3)	0.037 (2)
C19	0.1177 (7)	0.6456 (3)	−0.1562 (3)	0.023 (2)
C20	−0.0338 (8)	0.6773 (3)	−0.2214 (3)	0.030 (2)
C21	0.0615 (7)	0.6173 (4)	−0.0697 (2)	0.025 (2)
C22	0.1638 (7)	0.4292 (3)	−0.2232 (2)	0.020 (2)
C23	−0.0078 (7)	0.4211 (4)	−0.2880 (3)	0.033 (2)
C24	0.1471 (8)	0.3768 (3)	−0.1382 (3)	0.036 (2)
C25	0.2913 (7)	0.5964 (3)	−0.3109 (3)	0.021 (2)
C26	0.3151 (7)	0.6127 (3)	−0.3845 (3)	0.017 (2)
C27	0.3410 (8)	0.6270 (3)	−0.4736 (3)	0.019 (2)
C28	0.4912 (8)	0.6331 (3)	−0.4995 (3)	0.017 (2)
C29	0.5067 (7)	0.6407 (3)	−0.5952 (2)	0.025 (2)
C30	0.8457 (8)	0.6169 (4)	−0.4816 (3)	0.029 (2)
H1c1	1.376244	0.002944	−0.075455	0.0282*
H1c2	1.241435	0.151416	−0.091572	0.0424*
H2c2	1.116388	0.107715	−0.173665	0.0424*
H3c2	1.109193	0.070323	−0.079124	0.0424*
H1c3	1.299532	−0.127137	−0.170426	0.0457*
H2c3	1.133814	−0.092891	−0.13632	0.0457*
H3c3	1.166216	−0.066341	−0.230746	0.0457*
H1c4	1.479305	0.223423	−0.155782	0.0358*
H1c5	1.658532	0.223371	−0.261178	0.0387*
H2c5	1.744225	0.281742	−0.175356	0.0387*
H3c5	1.801238	0.176076	−0.194633	0.0387*
H1c6	1.563265	0.147225	−0.020427	0.0507*
H2c6	1.747074	0.138185	−0.043872	0.0507*
H3c6	1.673338	0.240525	−0.0271	0.0507*
H1c7	1.724579	0.008948	−0.235725	0.0348*
H1c8	1.557503	−0.073228	−0.347073	0.0476*
H2c8	1.678608	−0.147381	−0.295242	0.0476*
H3c8	1.488258	−0.14136	−0.281184	0.0476*
H1c9	1.737244	−0.02837	−0.084368	0.0468*
H2c9	1.616786	−0.118131	−0.114602	0.0468*
H3c9	1.800885	−0.115138	−0.13849	0.0468*
H1c12	1.258286	0.133915	−0.51255	0.0228*
H1c14	0.866192	0.087615	−0.601373	0.0289*
H2c14	0.867481	0.199881	−0.582963	0.0289*
H3c14	1.021046	0.151035	−0.618616	0.0289*
H1c15	0.60409	0.104084	−0.420364	0.0325*
H2c15	0.651284	0.168406	−0.495048	0.0325*
H3c15	0.671631	0.055986	−0.502019	0.0325*
H1c16	0.437372	0.537722	−0.07271	0.0302*
H1c17	0.476999	0.702007	−0.103506	0.0486*
H2c17	0.650654	0.652089	−0.071966	0.0486*
H3c17	0.591654	0.668702	−0.172783	0.0486*
H1c18	0.529875	0.41476	−0.159213	0.044*
H2c18	0.601303	0.490244	−0.218105	0.044*
H3c18	0.6882	0.480236	−0.119617	0.044*
H1c19	0.192976	0.700799	−0.142841	0.0274*
H1c20	0.003272	0.693641	−0.275654	0.0356*
H2c20	−0.11675	0.6255	−0.233082	0.0356*
H3c20	−0.08357	0.732735	−0.196811	0.0356*
H1c21	0.15746	0.59396	−0.030483	0.0304*
H2c21	0.016889	0.672803	−0.042273	0.0304*
H3c21	−0.024933	0.567433	−0.081919	0.0304*
H1c22	0.247839	0.397048	−0.251665	0.0239*
H1c23	0.004445	0.450839	−0.342194	0.0397*
H2c23	−0.039439	0.354201	−0.300158	0.0397*
H3c23	−0.094458	0.453365	−0.261631	0.0397*
H1c24	0.252428	0.382999	−0.097683	0.0435*
H2c24	0.057555	0.405184	−0.111254	0.0435*
H3c24	0.120787	0.309611	−0.152631	0.0435*
H1c29	0.57753	0.695675	−0.601908	0.0298*
H2c29	0.556607	0.583062	−0.61571	0.0298*
H3c29	0.395761	0.648324	−0.629351	0.0298*
H1c30	0.952545	0.626022	−0.442727	0.0345*
H2c30	0.839265	0.552943	−0.508694	0.0345*
H3c30	0.836947	0.663636	−0.5267	0.0345*
H1c27	0.241734	0.632529	−0.517744	0.0231*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0293 (13)	0.0165 (8)	0.0214 (6)	0.0004 (8)	0.0046 (8)	0.0021 (5)
S1	0.0263 (13)	0.0348 (11)	0.0262 (7)	0.0001 (9)	0.0052 (8)	−0.0006 (6)
C1	0.031 (5)	0.020 (3)	0.021 (2)	0.004 (3)	0.006 (3)	0.008 (2)
C2	0.034 (5)	0.035 (4)	0.040 (3)	0.010 (4)	0.013 (3)	0.011 (3)
C3	0.040 (5)	0.041 (4)	0.035 (3)	−0.013 (4)	0.011 (3)	0.005 (3)
C4	0.045 (5)	0.018 (3)	0.026 (2)	−0.008 (3)	0.005 (3)	0.002 (2)
C5	0.037 (5)	0.023 (3)	0.035 (3)	0.000 (3)	0.002 (3)	0.003 (2)
C6	0.061 (6)	0.031 (4)	0.033 (3)	−0.018 (4)	0.004 (3)	0.001 (2)
C7	0.041 (5)	0.020 (3)	0.029 (2)	0.005 (3)	0.016 (3)	0.000 (2)
C8	0.057 (6)	0.027 (3)	0.034 (3)	0.011 (4)	0.001 (3)	0.001 (2)
C9	0.052 (6)	0.025 (4)	0.040 (3)	0.015 (4)	0.005 (3)	−0.001 (2)
C10	0.018 (5)	0.012 (3)	0.031 (3)	−0.009 (3)	0.009 (3)	0.000 (2)
C11	0.017 (4)	0.015 (3)	0.027 (3)	−0.004 (3)	0.015 (3)	−0.001 (2)
C12	0.024 (5)	0.016 (3)	0.017 (2)	−0.003 (3)	0.003 (3)	0.004 (2)
C13	0.023 (5)	0.010 (3)	0.024 (3)	−0.007 (3)	0.004 (3)	0.003 (2)
C14	0.021 (4)	0.027 (3)	0.026 (2)	0.007 (3)	0.008 (3)	0.007 (2)
C15	0.021 (5)	0.019 (4)	0.042 (3)	0.002 (3)	0.008 (3)	0.001 (3)
Si2	0.0240 (13)	0.0141 (8)	0.0201 (6)	0.0001 (8)	0.0058 (8)	0.0031 (5)
S2	0.0201 (12)	0.0307 (10)	0.0251 (6)	0.0014 (8)	0.0042 (8)	0.0001 (6)
C16	0.027 (4)	0.027 (3)	0.024 (2)	0.002 (3)	0.013 (3)	0.004 (2)
C17	0.043 (5)	0.029 (4)	0.048 (3)	−0.001 (4)	0.006 (3)	−0.016 (3)
C18	0.029 (5)	0.023 (3)	0.057 (3)	0.006 (3)	0.005 (3)	0.003 (3)
C19	0.026 (5)	0.017 (3)	0.026 (2)	−0.003 (3)	0.004 (3)	0.001 (2)
C20	0.036 (5)	0.022 (3)	0.036 (3)	0.007 (3)	0.016 (3)	0.003 (2)
C21	0.019 (4)	0.028 (4)	0.028 (3)	0.000 (3)	0.002 (3)	0.001 (2)
C22	0.020 (5)	0.013 (3)	0.028 (2)	0.003 (3)	0.010 (3)	0.000 (2)
C23	0.045 (5)	0.019 (3)	0.038 (3)	−0.006 (3)	0.015 (3)	0.001 (2)
C24	0.044 (5)	0.020 (3)	0.045 (3)	−0.001 (4)	0.009 (3)	0.012 (2)
C25	0.022 (4)	0.012 (3)	0.028 (3)	−0.001 (3)	−0.002 (3)	0.000 (2)
C26	0.005 (4)	0.011 (3)	0.036 (3)	0.003 (3)	0.003 (3)	0.004 (2)
C27	0.021 (5)	0.016 (3)	0.021 (3)	0.002 (3)	0.002 (3)	−0.002 (2)
C28	0.016 (5)	0.019 (3)	0.015 (2)	0.007 (3)	0.001 (3)	0.004 (2)
C29	0.027 (5)	0.018 (3)	0.029 (2)	−0.001 (3)	0.004 (3)	0.007 (2)
C30	0.032 (5)	0.015 (4)	0.039 (3)	−0.003 (4)	0.004 (3)	0.004 (3)

Geometric parameters (Å, º) top

Si1—C1	1.890 (5)	Si2—C16	1.845 (5)
Si1—C4	1.880 (5)	Si2—C19	1.859 (5)
Si1—C7	1.865 (6)	Si2—C22	1.877 (4)
Si1—C10	1.839 (4)	Si2—C25	1.847 (5)
S1—C13	1.763 (6)	S2—C28	1.748 (5)
C1—C2	1.515 (7)	C16—C17	1.535 (7)
C1—C3	1.527 (7)	C16—C18	1.535 (8)
C1—H1c1	0.9575	C16—H1c16	0.96
C2—H1c2	0.9606	C17—H1c17	0.9574
C2—H2c2	0.9574	C17—H2c17	0.9572
C2—H3c2	0.9608	C17—H3c17	0.9602
C3—H1c3	0.9568	C18—H1c18	0.9612
C3—H2c3	0.9605	C18—H2c18	0.9598
C3—H3c3	0.9579	C18—H3c18	0.9574
C4—C5	1.515 (8)	C19—C20	1.518 (7)
C4—C6	1.539 (6)	C19—C21	1.530 (6)
C4—H1c4	0.9565	C19—H1c19	0.9611
C5—H1c5	0.9582	C20—H1c20	0.9602
C5—H2c5	0.9605	C20—H2c20	0.9611
C5—H3c5	0.9565	C20—H3c20	0.9582
C6—H1c6	0.961	C21—H1c21	0.9564
C6—H2c6	0.9564	C21—H2c21	0.9584
C6—H3c6	0.9603	C21—H3c21	0.961
C7—C8	1.530 (6)	C22—C23	1.553 (7)
C7—C9	1.529 (6)	C22—C24	1.541 (6)
C7—H1c7	0.9612	C22—H1c22	0.9581
C8—H1c8	0.9585	C23—H1c23	0.9599
C8—H2c8	0.9568	C23—H2c23	0.9606
C8—H3c8	0.9611	C23—H3c23	0.958
C9—H1c9	0.9598	C24—H1c24	0.9576
C9—H2c9	0.9613	C24—H2c24	0.9581
C9—H3c9	0.957	C24—H3c24	0.9604
C10—C11	1.197 (6)	C25—C26	1.204 (7)
C11—C12	1.420 (6)	C26—C27	1.434 (7)
C12—C13	1.333 (9)	C27—C28	1.323 (9)
C12—H1c12	0.9603	C27—H1c27	0.957
C13—C14	1.501 (6)	C28—C29	1.499 (6)
C14—H1c14	0.9609	C29—H1c29	0.9615
C14—H2c14	0.9571	C29—H2c29	0.9581
C14—H3c14	0.9602	C29—H3c29	0.9568
C15—H1c15	0.9602	C30—H1c30	0.9577
C15—H2c15	0.9584	C30—H2c30	0.9598
C15—H3c15	0.9596	C30—H3c30	0.9592

C1—Si1—C4	110.3 (2)	C16—Si2—C19	108.9 (2)
C1—Si1—C7	113.4 (2)	C16—Si2—C22	110.3 (2)
C1—Si1—C10	107.4 (2)	C16—Si2—C25	107.6 (2)
C4—Si1—C7	111.5 (2)	C19—Si2—C22	116.2 (2)
C4—Si1—C10	105.70 (19)	C19—Si2—C25	107.6 (2)
C7—Si1—C10	108.2 (2)	C22—Si2—C25	105.84 (19)
Si1—C1—C2	111.8 (3)	Si2—C16—C17	113.0 (3)
Si1—C1—C3	113.0 (3)	Si2—C16—C18	112.7 (3)
Si1—C1—H1c1	105.64	Si2—C16—H1c16	104.66
C2—C1—C3	109.9 (4)	C17—C16—C18	109.7 (5)
C2—C1—H1c1	108.67	C17—C16—H1c16	108.27
C3—C1—H1c1	107.7	C18—C16—H1c16	108.25
C1—C2—H1c2	109.52	C16—C17—H1c17	109.46
C1—C2—H2c2	109.29	C16—C17—H2c17	109.56
C1—C2—H3c2	109.43	C16—C17—H3c17	109.58
H1c2—C2—H2c2	109.44	H1c17—C17—H2c17	109.29
H1c2—C2—H3c2	109.59	H1c17—C17—H3c17	109.52
H2c2—C2—H3c2	109.54	H2c17—C17—H3c17	109.42
C1—C3—H1c3	109.54	C16—C18—H1c18	109.43
C1—C3—H2c3	109.59	C16—C18—H2c18	109.56
C1—C3—H3c3	109.43	C16—C18—H3c18	109.29
H1c3—C3—H2c3	109.37	H1c18—C18—H2c18	109.55
H1c3—C3—H3c3	109.31	H1c18—C18—H3c18	109.62
H2c3—C3—H3c3	109.58	H2c18—C18—H3c18	109.37
Si1—C4—C5	113.3 (3)	Si2—C19—C20	114.7 (3)
Si1—C4—C6	113.8 (3)	Si2—C19—C21	114.2 (3)
Si1—C4—H1c4	103.71	Si2—C19—H1c19	102.33
C5—C4—C6	109.8 (4)	C20—C19—C21	110.5 (4)
C5—C4—H1c4	108.26	C20—C19—H1c19	106.57
C6—C4—H1c4	107.52	C21—C19—H1c19	107.63
C4—C5—H1c5	109.55	C19—C20—H1c20	109.45
C4—C5—H2c5	109.6	C19—C20—H2c20	109.43
C4—C5—H3c5	109.42	C19—C20—H3c20	109.31
H1c5—C5—H2c5	109.47	H1c20—C20—H2c20	109.59
H1c5—C5—H3c5	109.32	H1c20—C20—H3c20	109.47
H2c5—C5—H3c5	109.46	H2c20—C20—H3c20	109.56
C4—C6—H1c6	109.53	C19—C21—H1c21	109.45
C4—C6—H2c6	109.32	C19—C21—H2c21	109.47
C4—C6—H3c6	109.5	C19—C21—H3c21	109.6
H1c6—C6—H2c6	109.45	H1c21—C21—H2c21	109.33
H1c6—C6—H3c6	109.61	H1c21—C21—H3c21	109.42
H2c6—C6—H3c6	109.42	H2c21—C21—H3c21	109.57
Si1—C7—C8	116.3 (4)	Si2—C22—C23	114.6 (3)
Si1—C7—C9	111.1 (3)	Si2—C22—C24	113.7 (3)
Si1—C7—H1c7	103.63	Si2—C22—H1c22	102.71
C8—C7—C9	110.6 (4)	C23—C22—C24	109.5 (4)
C8—C7—H1c7	104.44	C23—C22—H1c22	107.26
C9—C7—H1c7	110.28	C24—C22—H1c22	108.49
C7—C8—H1c8	109.41	C22—C23—H1c23	109.3
C7—C8—H2c8	109.53	C22—C23—H2c23	109.65
C7—C8—H3c8	109.53	C22—C23—H3c23	109.34
H1c8—C8—H2c8	109.3	H1c23—C23—H2c23	109.55
H1c8—C8—H3c8	109.66	H1c23—C23—H3c23	109.64
H2c8—C8—H3c8	109.39	H2c23—C23—H3c23	109.35
C7—C9—H1c9	109.43	C22—C24—H1c24	109.29
C7—C9—H2c9	109.62	C22—C24—H2c24	109.66
C7—C9—H3c9	109.27	C22—C24—H3c24	109.54
H1c9—C9—H2c9	109.54	H1c24—C24—H2c24	109.35
H1c9—C9—H3c9	109.51	H1c24—C24—H3c24	109.66
H2c9—C9—H3c9	109.46	H2c24—C24—H3c24	109.34
Si1—C10—C11	179.0 (5)	Si2—C25—C26	172.9 (4)
C10—C11—C12	177.7 (5)	C25—C26—C27	177.0 (5)
C11—C12—C13	124.7 (5)	C26—C27—C28	125.0 (5)
C11—C12—H1c12	117.66	C26—C27—H1c27	117.52
C13—C12—H1c12	117.63	C28—C27—H1c27	117.48
S1—C13—C12	119.1 (4)	S2—C28—C27	118.6 (3)
S1—C13—C14	118.7 (4)	S2—C28—C29	119.9 (4)
C12—C13—C14	122.2 (5)	C27—C28—C29	121.5 (4)
C13—C14—H1c14	109.41	C28—C29—H1c29	109.54
C13—C14—H2c14	109.32	C28—C29—H2c29	109.53
C13—C14—H3c14	109.6	C28—C29—H3c29	109.39
H1c14—C14—H2c14	109.59	H1c29—C29—H2c29	109.52
H1c14—C14—H3c14	109.58	H1c29—C29—H3c29	109.56
H2c14—C14—H3c14	109.34	H2c29—C29—H3c29	109.28
H1c15—C15—H2c15	109.67	H1c30—C30—H2c30	109.67
H1c15—C15—H3c15	109.35	H1c30—C30—H3c30	109.23
H2c15—C15—H3c15	109.51	H2c30—C30—H3c30	109.5

(Z_TIPS_2) top

Crystal data top

C₁₅H₂₈SSi	Z = 4
M_r = 268.5	F(000) = 592
Triclinic, P1	D_x = 1.061 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4082 (7) Å	Cell parameters from 9909 reflections
b = 11.2004 (8) Å	θ = 2.2–25.5°
c = 16.3446 (12) Å	µ = 0.25 mm⁻¹
α = 79.108 (3)°	T = 100 K
β = 83.424 (3)°	Plate, translucent colourless
γ = 89.300 (3)°	0.58 × 0.25 × 0.02 mm
V = 1680.1 (2) Å³

Data collection top

Bruker KAPPA APEX II CCD diffractometer	7746 independent reflections
Radiation source: X-ray tube	5684 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.044
ω– and φ–scans	θ_max = 27.7°, θ_min = 1.3°
Absorption correction: multi-scan SADABS	h = −12→12
T_min = 0.88, T_max = 0.99	k = −14→14
68578 measured reflections	l = −21→21

Refinement top

Refinement on F	224 constraints
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.043	Weighting scheme based on measured s.u.'s w = 1/(σ²(F) + 0.0001F²)
S = 1.95	(Δ/σ)_max = 0.049
7746 reflections	Δρ_max = 0.30 e Å⁻³
307 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints

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

	x	y	z	U_iso*/U_eq
Si1	0.80797 (4)	0.63981 (4)	0.17044 (3)	0.01776 (14)
S1	0.68556 (4)	0.56978 (4)	0.48764 (2)	0.02280 (13)
C1	0.91443 (16)	0.50469 (13)	0.21428 (10)	0.0225 (5)
C2	1.01568 (18)	0.53772 (15)	0.27368 (11)	0.0318 (6)
C3	0.82147 (19)	0.39572 (15)	0.25913 (11)	0.0335 (6)
C4	0.93028 (16)	0.77142 (13)	0.11948 (9)	0.0220 (5)
C5	0.84675 (18)	0.88247 (14)	0.08188 (10)	0.0305 (6)
C6	1.0491 (2)	0.74110 (16)	0.05477 (12)	0.0411 (7)
C7	0.68326 (18)	0.60478 (16)	0.09566 (10)	0.0310 (6)
C8	0.54161 (19)	0.54515 (18)	0.13882 (13)	0.0475 (8)
C9	0.7566 (2)	0.5302 (2)	0.03343 (12)	0.0531 (8)
C10	0.70253 (16)	0.68714 (14)	0.26003 (10)	0.0211 (5)
C11	0.63897 (16)	0.71789 (13)	0.32130 (10)	0.0201 (5)
C12	0.56484 (16)	0.75455 (14)	0.39326 (10)	0.0211 (5)
C13	0.57437 (15)	0.69672 (13)	0.47208 (9)	0.0187 (5)
C14	0.49405 (17)	0.73856 (14)	0.54604 (10)	0.0269 (6)
C15	0.66216 (18)	0.51693 (16)	0.59961 (10)	0.0301 (6)
Si2	0.37589 (4)	0.06149 (4)	0.22404 (3)	0.01767 (14)
S2	0.04828 (4)	0.21978 (4)	0.43766 (2)	0.02334 (13)
C16	0.24161 (16)	0.15886 (14)	0.16614 (10)	0.0246 (5)
C17	0.23375 (18)	0.28498 (15)	0.18939 (11)	0.0354 (6)
C18	0.09200 (17)	0.10114 (17)	0.18030 (12)	0.0405 (7)
C19	0.55287 (15)	0.14454 (14)	0.20886 (9)	0.0206 (5)
C20	0.66060 (16)	0.07592 (15)	0.26318 (10)	0.0259 (6)
C21	0.61727 (17)	0.17853 (15)	0.11664 (10)	0.0296 (6)
C22	0.39586 (17)	−0.09381 (13)	0.19545 (9)	0.0217 (5)
C23	0.28555 (17)	−0.18807 (14)	0.24536 (10)	0.0262 (6)
C24	0.3970 (2)	−0.09035 (17)	0.10137 (11)	0.0410 (7)
C25	0.31276 (15)	0.04172 (13)	0.33622 (10)	0.0191 (5)
C26	0.27108 (15)	0.03757 (13)	0.40921 (10)	0.0191 (5)
C27	0.21904 (15)	0.03924 (14)	0.49453 (9)	0.0201 (5)
C28	0.11981 (15)	0.11756 (13)	0.51723 (9)	0.0174 (5)
C29	0.07033 (16)	0.11840 (15)	0.60741 (9)	0.0240 (5)
C30	−0.07370 (19)	0.30796 (17)	0.49406 (11)	0.0358 (7)
H1c1	0.969028	0.481105	0.166685	0.027*
H1c2	1.082196	0.59924	0.243449	0.0382*
H2c2	0.961225	0.567872	0.318707	0.0382*
H3c2	1.067117	0.466756	0.296125	0.0382*
H1c3	0.764668	0.370083	0.220278	0.0403*
H2c3	0.881591	0.330177	0.280773	0.0403*
H3c3	0.759712	0.418414	0.304523	0.0403*
H1c4	0.977515	0.790723	0.164455	0.0264*
H1c5	0.771688	0.899324	0.122975	0.0366*
H2c5	0.910174	0.951448	0.065242	0.0366*
H3c5	0.805964	0.86632	0.033809	0.0366*
H1c6	1.10174	0.672448	0.079779	0.0493*
H2c6	1.007693	0.722023	0.007727	0.0493*
H3c6	1.112538	0.809801	0.036189	0.0493*
H1c7	0.658925	0.682583	0.064813	0.0372*
H1c8	0.493901	0.596804	0.173736	0.057*
H2c8	0.481886	0.533302	0.097124	0.057*
H3c8	0.560308	0.467983	0.172651	0.057*
H1c9	0.839337	0.573585	0.002802	0.0637*
H2c9	0.785188	0.453209	0.063523	0.0637*
H3c9	0.691027	0.516983	−0.004966	0.0637*
H1c12	0.504643	0.82461	0.384882	0.0253*
H1c14	0.430282	0.675051	0.576466	0.0323*
H2c14	0.560563	0.757895	0.58209	0.0323*
H3c14	0.43989	0.809511	0.526924	0.0323*
H1c15	0.722552	0.448211	0.613896	0.0361*
H2c15	0.687435	0.580931	0.627047	0.0361*
H3c15	0.564043	0.493517	0.6175	0.0361*
H1c16	0.274873	0.166319	0.107626	0.0295*
H1c17	0.324917	0.325268	0.173228	0.0425*
H2c17	0.162096	0.331929	0.160677	0.0425*
H3c17	0.209289	0.276922	0.248843	0.0425*
H1c18	0.09515	0.02733	0.158379	0.0486*
H2c18	0.060167	0.083262	0.23928	0.0486*
H3c18	0.026852	0.15665	0.152101	0.0486*
H1c19	0.531984	0.219933	0.227342	0.0247*
H1c20	0.619404	0.059249	0.320729	0.0311*
H2c20	0.684482	0.000768	0.245034	0.0311*
H3c20	0.745576	0.124651	0.257916	0.0311*
H1c21	0.551031	0.228082	0.084944	0.0355*
H2c21	0.705119	0.222891	0.11311	0.0355*
H3c21	0.635876	0.105831	0.094272	0.0355*
H1c22	0.48808	−0.120137	0.211135	0.026*
H1c23	0.288261	−0.191686	0.304316	0.0314*
H2c23	0.191639	−0.164896	0.231042	0.0314*
H3c23	0.307887	−0.266465	0.231894	0.0314*
H1c24	0.470886	−0.035634	0.071024	0.0492*
H2c24	0.414809	−0.170377	0.089704	0.0492*
H3c24	0.305942	−0.062855	0.084345	0.0492*
H1c27	0.256825	−0.018393	0.537747	0.0241*
H1c29	−0.030481	0.101057	0.618254	0.0288*
H2c29	0.120881	0.057701	0.642316	0.0288*
H3c29	0.088819	0.196971	0.619535	0.0288*
H1c30	−0.11822	0.367548	0.45501	0.0429*
H2c30	−0.145759	0.255384	0.5286	0.0429*
H3c30	−0.022416	0.348162	0.528757	0.0429*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1	0.0200 (2)	0.0170 (2)	0.0164 (2)	−0.00208 (17)	−0.00310 (17)	−0.00273 (17)
S1	0.0241 (2)	0.0218 (2)	0.0219 (2)	0.00131 (17)	−0.00450 (17)	−0.00186 (17)
C1	0.0257 (9)	0.0200 (9)	0.0221 (9)	0.0019 (7)	−0.0025 (7)	−0.0051 (7)
C2	0.0304 (10)	0.0238 (10)	0.0415 (11)	0.0005 (7)	−0.0149 (8)	−0.0002 (8)
C3	0.0425 (11)	0.0203 (9)	0.0380 (11)	−0.0046 (8)	−0.0165 (9)	0.0015 (8)
C4	0.0228 (8)	0.0227 (9)	0.0200 (8)	−0.0028 (7)	−0.0025 (7)	−0.0026 (7)
C5	0.0376 (11)	0.0212 (9)	0.0295 (10)	−0.0048 (8)	−0.0017 (8)	0.0020 (7)
C6	0.0361 (11)	0.0375 (12)	0.0428 (12)	−0.0038 (9)	0.0122 (9)	−0.0001 (9)
C7	0.0381 (10)	0.0280 (10)	0.0276 (9)	−0.0089 (8)	−0.0143 (8)	−0.0005 (8)
C8	0.0401 (11)	0.0507 (14)	0.0541 (14)	−0.0146 (10)	−0.0232 (10)	−0.0042 (10)
C9	0.0733 (15)	0.0609 (15)	0.0305 (11)	−0.0241 (12)	−0.0122 (10)	−0.0170 (10)
C10	0.0214 (8)	0.0192 (9)	0.0214 (8)	−0.0009 (7)	−0.0041 (7)	0.0009 (7)
C11	0.0193 (8)	0.0167 (8)	0.0229 (8)	−0.0014 (6)	−0.0052 (7)	0.0011 (7)
C12	0.0210 (8)	0.0170 (9)	0.0250 (9)	0.0014 (6)	−0.0011 (7)	−0.0042 (7)
C13	0.0168 (8)	0.0173 (8)	0.0223 (8)	−0.0048 (6)	−0.0008 (6)	−0.0056 (6)
C14	0.0305 (10)	0.0259 (10)	0.0240 (9)	−0.0023 (7)	0.0021 (7)	−0.0068 (7)
C15	0.0337 (10)	0.0319 (11)	0.0232 (9)	−0.0040 (8)	−0.0087 (7)	0.0020 (7)
Si2	0.0178 (2)	0.0190 (2)	0.0156 (2)	−0.00041 (17)	−0.00154 (17)	−0.00198 (17)
S2	0.0276 (2)	0.0217 (2)	0.0195 (2)	0.00275 (17)	−0.00245 (17)	−0.00105 (16)
C16	0.0232 (9)	0.0295 (10)	0.0185 (8)	0.0018 (7)	−0.0019 (7)	0.0015 (7)
C17	0.0320 (10)	0.0319 (11)	0.0378 (11)	0.0099 (8)	−0.0023 (8)	0.0030 (8)
C18	0.0264 (10)	0.0472 (12)	0.0439 (12)	0.0019 (8)	−0.0149 (9)	0.0077 (9)
C19	0.0206 (8)	0.0169 (9)	0.0238 (8)	0.0003 (7)	0.0002 (7)	−0.0045 (7)
C20	0.0199 (9)	0.0243 (9)	0.0336 (10)	−0.0028 (7)	−0.0048 (7)	−0.0045 (7)
C21	0.0272 (9)	0.0287 (10)	0.0297 (9)	−0.0031 (7)	0.0040 (8)	−0.0015 (7)
C22	0.0228 (9)	0.0227 (9)	0.0198 (8)	−0.0025 (7)	−0.0016 (7)	−0.0050 (7)
C23	0.0260 (9)	0.0221 (9)	0.0308 (9)	−0.0045 (7)	−0.0043 (7)	−0.0051 (7)
C24	0.0662 (14)	0.0337 (11)	0.0239 (10)	−0.0107 (10)	−0.0015 (9)	−0.0091 (8)
C25	0.0175 (8)	0.0174 (8)	0.0224 (9)	−0.0012 (6)	−0.0038 (6)	−0.0027 (6)
C26	0.0167 (8)	0.0165 (8)	0.0246 (9)	−0.0007 (6)	−0.0045 (7)	−0.0036 (6)
C27	0.0201 (8)	0.0220 (9)	0.0167 (8)	−0.0014 (7)	−0.0029 (6)	0.0005 (6)
C28	0.0151 (8)	0.0186 (8)	0.0183 (8)	−0.0040 (6)	−0.0024 (6)	−0.0028 (6)
C29	0.0193 (8)	0.0324 (10)	0.0195 (8)	0.0007 (7)	−0.0011 (7)	−0.0037 (7)
C30	0.0363 (11)	0.0368 (11)	0.0337 (10)	0.0144 (9)	−0.0037 (8)	−0.0066 (8)

Geometric parameters (Å, º) top

Si1—C1	1.8773 (15)	Si2—C16	1.8790 (16)
Si1—C4	1.8838 (15)	Si2—C19	1.8855 (15)
Si1—C7	1.8830 (19)	Si2—C22	1.8865 (17)
Si1—C10	1.8321 (16)	Si2—C25	1.8340 (16)
S1—C13	1.7517 (15)	S2—C28	1.7532 (14)
C1—C2	1.531 (3)	C16—C17	1.529 (2)
C1—C3	1.527 (2)	C16—C18	1.531 (2)
C1—H1c1	0.96	C16—H1c16	0.96
C2—H1c2	0.96	C17—H1c17	0.96
C2—H2c2	0.96	C17—H2c17	0.96
C2—H3c2	0.96	C17—H3c17	0.96
C3—H1c3	0.96	C18—H1c18	0.96
C3—H2c3	0.96	C18—H2c18	0.96
C3—H3c3	0.96	C18—H3c18	0.96
C4—C5	1.530 (2)	C19—C20	1.528 (2)
C4—C6	1.530 (2)	C19—C21	1.537 (2)
C4—H1c4	0.96	C19—H1c19	0.96
C5—H1c5	0.96	C20—H1c20	0.96
C5—H2c5	0.96	C20—H2c20	0.96
C5—H3c5	0.96	C20—H3c20	0.96
C6—H1c6	0.96	C21—H1c21	0.96
C6—H2c6	0.96	C21—H2c21	0.96
C6—H3c6	0.96	C21—H3c21	0.96
C7—C8	1.532 (2)	C22—C23	1.538 (2)
C7—C9	1.535 (3)	C22—C24	1.530 (2)
C7—H1c7	0.96	C22—H1c22	0.96
C8—H1c8	0.96	C23—H1c23	0.96
C8—H2c8	0.96	C23—H2c23	0.96
C8—H3c8	0.96	C23—H3c23	0.96
C9—H1c9	0.96	C24—H1c24	0.96
C9—H2c9	0.96	C24—H2c24	0.96
C9—H3c9	0.96	C24—H3c24	0.96
C10—C11	1.211 (2)	C25—C26	1.205 (2)
C11—C12	1.423 (2)	C26—C27	1.428 (2)
C12—C13	1.340 (2)	C27—C28	1.343 (2)
C12—H1c12	0.96	C27—H1c27	0.96
C13—C14	1.499 (2)	C28—C29	1.496 (2)
C14—H1c14	0.96	C29—H1c29	0.96
C14—H2c14	0.96	C29—H2c29	0.96
C14—H3c14	0.96	C29—H3c29	0.96
C15—H1c15	0.96	C30—H1c30	0.96
C15—H2c15	0.96	C30—H2c30	0.96
C15—H3c15	0.96	C30—H3c30	0.96

C1—Si1—C4	110.56 (7)	C16—Si2—C19	109.94 (7)
C1—Si1—C7	112.98 (8)	C16—Si2—C22	113.27 (8)
C1—Si1—C10	106.60 (7)	C16—Si2—C25	107.11 (7)
C4—Si1—C7	110.89 (7)	C19—Si2—C22	111.74 (7)
C4—Si1—C10	106.46 (7)	C19—Si2—C25	106.15 (7)
C7—Si1—C10	109.04 (7)	C22—Si2—C25	108.24 (7)
Si1—C1—C2	111.19 (11)	Si2—C16—C17	111.01 (12)
Si1—C1—C3	113.32 (11)	Si2—C16—C18	113.09 (11)
Si1—C1—H1c1	105.57	Si2—C16—H1c16	105.97
C2—C1—C3	109.52 (13)	C17—C16—C18	109.79 (14)
C2—C1—H1c1	109.68	C17—C16—H1c16	109.52
C3—C1—H1c1	107.38	C18—C16—H1c16	107.29
C1—C2—H1c2	109.47	C16—C17—H1c17	109.47
C1—C2—H2c2	109.47	C16—C17—H2c17	109.47
C1—C2—H3c2	109.47	C16—C17—H3c17	109.47
H1c2—C2—H2c2	109.47	H1c17—C17—H2c17	109.47
H1c2—C2—H3c2	109.47	H1c17—C17—H3c17	109.47
H2c2—C2—H3c2	109.47	H2c17—C17—H3c17	109.47
C1—C3—H1c3	109.47	C16—C18—H1c18	109.47
C1—C3—H2c3	109.47	C16—C18—H2c18	109.47
C1—C3—H3c3	109.47	C16—C18—H3c18	109.47
H1c3—C3—H2c3	109.47	H1c18—C18—H2c18	109.47
H1c3—C3—H3c3	109.47	H1c18—C18—H3c18	109.47
H2c3—C3—H3c3	109.47	H2c18—C18—H3c18	109.47
Si1—C4—C5	111.82 (10)	Si2—C19—C20	112.03 (10)
Si1—C4—C6	114.50 (11)	Si2—C19—C21	113.68 (12)
Si1—C4—H1c4	104.54	Si2—C19—H1c19	105.21
C5—C4—C6	110.60 (12)	C20—C19—C21	111.17 (12)
C5—C4—H1c4	108.97	C20—C19—H1c19	108.06
C6—C4—H1c4	105.93	C21—C19—H1c19	106.19
C4—C5—H1c5	109.47	C19—C20—H1c20	109.47
C4—C5—H2c5	109.47	C19—C20—H2c20	109.47
C4—C5—H3c5	109.47	C19—C20—H3c20	109.47
H1c5—C5—H2c5	109.47	H1c20—C20—H2c20	109.47
H1c5—C5—H3c5	109.47	H1c20—C20—H3c20	109.47
H2c5—C5—H3c5	109.47	H2c20—C20—H3c20	109.47
C4—C6—H1c6	109.47	C19—C21—H1c21	109.47
C4—C6—H2c6	109.47	C19—C21—H2c21	109.47
C4—C6—H3c6	109.47	C19—C21—H3c21	109.47
H1c6—C6—H2c6	109.47	H1c21—C21—H2c21	109.47
H1c6—C6—H3c6	109.47	H1c21—C21—H3c21	109.47
H2c6—C6—H3c6	109.47	H2c21—C21—H3c21	109.47
Si1—C7—C8	113.99 (12)	Si2—C22—C23	113.96 (11)
Si1—C7—C9	111.93 (12)	Si2—C22—C24	112.87 (11)
Si1—C7—H1c7	104.99	Si2—C22—H1c22	103.99
C8—C7—C9	110.99 (16)	C23—C22—C24	110.16 (14)
C8—C7—H1c7	106.05	C23—C22—H1c22	107.07
C9—C7—H1c7	108.38	C24—C22—H1c22	108.3
C7—C8—H1c8	109.47	C22—C23—H1c23	109.47
C7—C8—H2c8	109.47	C22—C23—H2c23	109.47
C7—C8—H3c8	109.47	C22—C23—H3c23	109.47
H1c8—C8—H2c8	109.47	H1c23—C23—H2c23	109.47
H1c8—C8—H3c8	109.47	H1c23—C23—H3c23	109.47
H2c8—C8—H3c8	109.47	H2c23—C23—H3c23	109.47
C7—C9—H1c9	109.47	C22—C24—H1c24	109.47
C7—C9—H2c9	109.47	C22—C24—H2c24	109.47
C7—C9—H3c9	109.47	C22—C24—H3c24	109.47
H1c9—C9—H2c9	109.47	H1c24—C24—H2c24	109.47
H1c9—C9—H3c9	109.47	H1c24—C24—H3c24	109.47
H2c9—C9—H3c9	109.47	H2c24—C24—H3c24	109.47
Si1—C10—C11	176.70 (15)	Si2—C25—C26	175.36 (14)
C10—C11—C12	179.69 (16)	C25—C26—C27	176.89 (16)
C11—C12—C13	123.68 (14)	C26—C27—C28	123.15 (13)
C11—C12—H1c12	118.16	C26—C27—H1c27	118.43
C13—C12—H1c12	118.16	C28—C27—H1c27	118.43
S1—C13—C12	118.27 (12)	S2—C28—C27	118.00 (11)
S1—C13—C14	119.91 (11)	S2—C28—C29	120.40 (11)
C12—C13—C14	121.82 (14)	C27—C28—C29	121.60 (13)
C13—C14—H1c14	109.47	C28—C29—H1c29	109.47
C13—C14—H2c14	109.47	C28—C29—H2c29	109.47
C13—C14—H3c14	109.47	C28—C29—H3c29	109.47
H1c14—C14—H2c14	109.47	H1c29—C29—H2c29	109.47
H1c14—C14—H3c14	109.47	H1c29—C29—H3c29	109.47
H2c14—C14—H3c14	109.47	H2c29—C29—H3c29	109.47
H1c15—C15—H2c15	109.47	H1c30—C30—H2c30	109.47
H1c15—C15—H3c15	109.47	H1c30—C30—H3c30	109.47
H2c15—C15—H3c15	109.47	H2c30—C30—H3c30	109.47

(Z_TBDMS) top

Crystal data top

C₁₂H₂₂SSi	Z = 4
M_r = 226.5	F(000) = 496
Triclinic, P1	D_x = 1.076 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 6.2535 (7) Å	Cell parameters from 5994 reflections
b = 7.2501 (8) Å	θ = 2.5–27.5°
c = 32.335 (4) Å	µ = 0.28 mm⁻¹
α = 92.496 (6)°	T = 100 K
β = 91.452 (6)°	Plate, translucent colourless
γ = 107.191 (6)°	0.64 × 0.34 × 0.04 mm
V = 1398.1 (3) Å³

Data collection top

Bruker KAPPA APEX II CCD diffractometer	4971 independent reflections
Radiation source: X-ray tube	4548 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.046
ω– and φ–scans	θ_max = 28.0°, θ_min = 0.6°
Absorption correction: multi-scan SADABS	h = −8→8
T_min = 0.89, T_max = 0.99	k = −9→9
22518 measured reflections	l = 0→42

Refinement top

Refinement on F	176 constraints
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.055	Weighting scheme based on measured s.u.'s w = 1/(σ²(F) + 0.0001F²)
S = 2.37	(Δ/σ)_max = 0.044
4971 reflections	Δρ_max = 0.30 e Å⁻³
254 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints

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

	x	y	z	U_iso*/U_eq
S1	0.25929 (11)	0.31670 (11)	0.00005 (2)	0.0174 (2)
Si1	0.34073 (12)	0.27918 (12)	0.16192 (3)	0.0154 (3)
C1	0.3512 (5)	0.0233 (4)	0.16602 (9)	0.0197 (10)
C2	0.4891 (5)	−0.0251 (5)	0.13067 (10)	0.0297 (12)
C3	0.4611 (5)	0.0006 (5)	0.20769 (9)	0.0283 (11)
C4	0.1137 (5)	−0.1178 (5)	0.16239 (11)	0.0325 (13)
C5	0.6290 (5)	0.4494 (5)	0.15971 (10)	0.0235 (12)
C6	0.1963 (5)	0.3506 (5)	0.20689 (9)	0.0283 (11)
C7	0.1766 (5)	0.2852 (4)	0.11416 (9)	0.0185 (10)
C8	0.0547 (4)	0.2626 (4)	0.08367 (8)	0.0154 (9)
C9	−0.0945 (5)	0.2267 (4)	0.04782 (9)	0.0183 (9)
C10	−0.0296 (4)	0.2421 (4)	0.00893 (9)	0.0152 (9)
C11	−0.1926 (5)	0.1948 (4)	−0.02734 (8)	0.0185 (10)
C12	0.2730 (5)	0.3210 (4)	−0.05577 (9)	0.0210 (10)
S2	0.24079 (13)	0.18330 (12)	0.50013 (2)	0.0248 (3)
Si2	0.22711 (14)	0.30023 (13)	0.66192 (3)	0.0213 (3)
C13	0.2189 (5)	0.5586 (5)	0.66524 (9)	0.0238 (11)
C14	0.0649 (6)	0.5925 (5)	0.63083 (10)	0.0330 (13)
C15	0.1261 (5)	0.6026 (5)	0.70723 (9)	0.0313 (12)
C16	0.4545 (6)	0.7002 (5)	0.66177 (11)	0.0349 (14)
C17	−0.0588 (6)	0.1326 (5)	0.66028 (11)	0.0325 (14)
C18	0.3903 (6)	0.2515 (6)	0.70669 (9)	0.0351 (13)
C19	0.3709 (5)	0.2713 (4)	0.61420 (9)	0.0239 (11)
C20	0.4803 (5)	0.2780 (4)	0.58386 (8)	0.0213 (10)
C21	0.6150 (5)	0.2941 (5)	0.54806 (8)	0.0228 (11)
C22	0.5309 (5)	0.2610 (4)	0.50848 (9)	0.0187 (10)
C23	0.6814 (5)	0.2920 (5)	0.47260 (9)	0.0257 (11)
C24	0.2033 (5)	0.1514 (5)	0.44477 (8)	0.0296 (12)
H1c2	0.639825	0.059552	0.133474	0.0357*
H2c2	0.490621	−0.156714	0.131943	0.0357*
H3c2	0.423008	−0.00818	0.104528	0.0357*
H1c3	0.61112	0.086659	0.209975	0.034*
H2c3	0.376026	0.031331	0.229864	0.034*
H3c3	0.464743	−0.130302	0.209317	0.034*
H1c4	0.050159	−0.115685	0.135137	0.039*
H2c4	0.119423	−0.246101	0.167148	0.039*
H3c4	0.02262	−0.080147	0.182611	0.039*
H1c5	0.716277	0.438419	0.183829	0.0282*
H2c5	0.698137	0.417975	0.135303	0.0282*
H3c5	0.621045	0.579398	0.158877	0.0282*
H1c6	0.274757	0.340041	0.232158	0.034*
H2c6	0.194373	0.481743	0.204715	0.034*
H3c6	0.045311	0.266778	0.206953	0.034*
H1c9	−0.252485	0.188943	0.052204	0.022*
H1c11	−0.1824	0.310005	−0.041726	0.0222*
H2c11	−0.158493	0.100805	−0.045758	0.0222*
H3c11	−0.341723	0.143252	−0.017868	0.0222*
H1c12	0.426506	0.368986	−0.063165	0.0252*
H2c12	0.208757	0.192462	−0.067857	0.0252*
H3c12	0.190899	0.403816	−0.065878	0.0252*
H1c14	−0.087427	0.521675	0.635714	0.0396*
H2c14	0.079049	0.727889	0.630538	0.0396*
H3c14	0.106395	0.54904	0.604602	0.0396*
H1c15	0.232012	0.602084	0.72921	0.0375*
H2c15	0.101894	0.727309	0.707177	0.0375*
H3c15	−0.013059	0.505691	0.711347	0.0375*
H1c16	0.544642	0.696193	0.685987	0.0418*
H2c16	0.522094	0.664069	0.637621	0.0418*
H3c16	0.443815	0.828837	0.659519	0.0418*
H1c17	−0.131571	0.152182	0.685168	0.039*
H2c17	−0.141743	0.15625	0.636735	0.039*
H3c17	−0.052444	0.001878	0.658071	0.039*
H1c18	0.314543	0.26184	0.73174	0.0421*
H2c18	0.404194	0.12341	0.703093	0.0421*
H3c18	0.536702	0.343912	0.708395	0.0421*
H1c21	0.774803	0.330662	0.552467	0.0273*
H1c23	0.657994	0.393765	0.456728	0.0309*
H2c23	0.834661	0.327273	0.482632	0.0309*
H3c23	0.64813	0.174988	0.455387	0.0309*
H1c24	0.047204	0.094547	0.437405	0.0355*
H2c24	0.256426	0.27471	0.432745	0.0355*
H3c24	0.286332	0.067978	0.434545	0.0355*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0091 (3)	0.0130 (4)	0.0279 (4)	0.0000 (3)	−0.0007 (3)	0.0005 (3)
Si1	0.0113 (4)	0.0098 (4)	0.0249 (5)	0.0027 (3)	−0.0006 (3)	0.0015 (3)
C1	0.0163 (14)	0.0102 (17)	0.0305 (16)	0.0010 (12)	−0.0056 (12)	0.0025 (12)
C2	0.0334 (19)	0.0223 (18)	0.0371 (19)	0.0155 (14)	−0.0061 (14)	−0.0064 (15)
C3	0.0257 (17)	0.0200 (17)	0.0375 (18)	0.0046 (14)	−0.0101 (14)	0.0050 (15)
C4	0.030 (2)	0.0071 (19)	0.054 (2)	−0.0041 (14)	−0.0073 (16)	0.0099 (16)
C5	0.0232 (18)	0.0101 (19)	0.0334 (18)	−0.0019 (13)	−0.0002 (13)	0.0075 (14)
C6	0.0248 (17)	0.0253 (18)	0.0368 (18)	0.0109 (14)	−0.0003 (14)	−0.0008 (15)
C7	0.0166 (14)	0.0104 (15)	0.0290 (16)	0.0044 (12)	0.0057 (12)	0.0013 (11)
C8	0.0144 (14)	0.0070 (15)	0.0267 (15)	0.0056 (11)	0.0052 (11)	0.0019 (11)
C9	0.0108 (13)	0.0102 (15)	0.0348 (16)	0.0042 (11)	0.0009 (12)	0.0038 (12)
C10	0.0114 (14)	0.0045 (14)	0.0306 (15)	0.0036 (11)	−0.0013 (11)	0.0026 (12)
C11	0.0161 (15)	0.0118 (15)	0.0265 (16)	0.0031 (12)	−0.0041 (12)	0.0006 (12)
C12	0.0204 (15)	0.0134 (16)	0.0300 (16)	0.0058 (12)	0.0050 (12)	0.0010 (12)
S2	0.0272 (5)	0.0349 (5)	0.0121 (3)	0.0089 (4)	0.0002 (3)	0.0024 (3)
Si2	0.0249 (5)	0.0269 (5)	0.0119 (4)	0.0074 (4)	0.0002 (3)	0.0006 (3)
C13	0.0237 (17)	0.0269 (19)	0.0195 (15)	0.0058 (13)	0.0033 (12)	−0.0002 (13)
C14	0.043 (2)	0.038 (2)	0.0233 (17)	0.0205 (16)	0.0020 (15)	0.0034 (15)
C15	0.038 (2)	0.036 (2)	0.0183 (15)	0.0101 (17)	0.0027 (14)	−0.0060 (15)
C16	0.034 (2)	0.033 (2)	0.0341 (19)	0.0047 (16)	0.0094 (15)	0.0012 (17)
C17	0.033 (2)	0.027 (2)	0.0340 (19)	0.0046 (16)	0.0060 (15)	−0.0025 (16)
C18	0.046 (2)	0.046 (2)	0.0189 (15)	0.0237 (18)	−0.0004 (14)	0.0037 (16)
C19	0.0264 (17)	0.0277 (18)	0.0183 (15)	0.0096 (14)	−0.0036 (12)	−0.0024 (12)
C20	0.0242 (16)	0.0251 (17)	0.0162 (14)	0.0104 (13)	−0.0041 (12)	−0.0012 (12)
C21	0.0242 (16)	0.0296 (19)	0.0134 (14)	0.0060 (13)	0.0042 (11)	0.0015 (12)
C22	0.0215 (16)	0.0179 (16)	0.0176 (14)	0.0067 (12)	0.0021 (12)	0.0041 (12)
C23	0.0282 (17)	0.030 (2)	0.0211 (15)	0.0114 (14)	0.0025 (13)	0.0040 (13)
C24	0.0321 (18)	0.041 (2)	0.0139 (14)	0.0084 (16)	−0.0006 (13)	0.0040 (14)

Geometric parameters (Å, º) top

S1—C10	1.761 (3)	S2—C22	1.743 (3)
Si1—C1	1.886 (3)	Si2—C13	1.888 (4)
Si1—C5	1.865 (3)	Si2—C17	1.839 (3)
Si1—C6	1.865 (3)	Si2—C18	1.856 (4)
Si1—C7	1.842 (3)	Si2—C19	1.841 (3)
C1—C2	1.539 (5)	C13—C14	1.528 (5)
C1—C3	1.534 (4)	C13—C15	1.547 (4)
C1—C4	1.533 (4)	C13—C16	1.537 (4)
C2—H1c2	0.96	C14—H1c14	0.96
C2—H2c2	0.96	C14—H2c14	0.96
C2—H3c2	0.96	C14—H3c14	0.96
C3—H1c3	0.96	C15—H1c15	0.96
C3—H2c3	0.96	C15—H2c15	0.96
C3—H3c3	0.96	C15—H3c15	0.96
C4—H1c4	0.96	C16—H1c16	0.96
C4—H2c4	0.96	C16—H2c16	0.96
C4—H3c4	0.96	C16—H3c16	0.96
C5—H1c5	0.96	C17—H1c17	0.96
C5—H2c5	0.96	C17—H2c17	0.96
C5—H3c5	0.96	C17—H3c17	0.96
C6—H1c6	0.96	C18—H1c18	0.96
C6—H2c6	0.96	C18—H2c18	0.96
C6—H3c6	0.96	C18—H3c18	0.96
C7—C8	1.206 (4)	C19—C20	1.205 (4)
C8—C9	1.434 (4)	C20—C21	1.437 (4)
C9—C10	1.330 (4)	C21—C22	1.355 (4)
C9—H1c9	0.96	C21—H1c21	0.96
C10—C11	1.493 (4)	C22—C23	1.495 (4)
C11—H1c11	0.96	C23—H1c23	0.96
C11—H2c11	0.96	C23—H2c23	0.96
C11—H3c11	0.96	C23—H3c23	0.96
C12—H1c12	0.96	C24—H1c24	0.96
C12—H2c12	0.96	C24—H2c24	0.96
C12—H3c12	0.96	C24—H3c24	0.96

C1—Si1—C5	110.55 (15)	C13—Si2—C17	110.29 (17)
C1—Si1—C6	110.25 (15)	C13—Si2—C18	110.85 (15)
C1—Si1—C7	107.36 (13)	C13—Si2—C19	106.44 (14)
C5—Si1—C6	109.91 (14)	C17—Si2—C18	109.68 (16)
C5—Si1—C7	110.16 (14)	C17—Si2—C19	110.94 (14)
C6—Si1—C7	108.55 (15)	C18—Si2—C19	108.57 (16)
Si1—C1—C2	109.0 (2)	Si2—C13—C14	110.6 (2)
Si1—C1—C3	110.5 (2)	Si2—C13—C15	109.8 (2)
Si1—C1—C4	110.1 (2)	Si2—C13—C16	110.9 (3)
C2—C1—C3	109.2 (3)	C14—C13—C15	107.8 (3)
C2—C1—C4	109.2 (2)	C14—C13—C16	109.1 (3)
C3—C1—C4	108.9 (2)	C15—C13—C16	108.5 (2)
C1—C2—H1c2	109.47	C13—C14—H1c14	109.47
C1—C2—H2c2	109.47	C13—C14—H2c14	109.47
C1—C2—H3c2	109.47	C13—C14—H3c14	109.47
H1c2—C2—H2c2	109.47	H1c14—C14—H2c14	109.47
H1c2—C2—H3c2	109.47	H1c14—C14—H3c14	109.47
H2c2—C2—H3c2	109.47	H2c14—C14—H3c14	109.47
C1—C3—H1c3	109.47	C13—C15—H1c15	109.47
C1—C3—H2c3	109.47	C13—C15—H2c15	109.47
C1—C3—H3c3	109.47	C13—C15—H3c15	109.47
H1c3—C3—H2c3	109.47	H1c15—C15—H2c15	109.47
H1c3—C3—H3c3	109.47	H1c15—C15—H3c15	109.47
H2c3—C3—H3c3	109.47	H2c15—C15—H3c15	109.47
C1—C4—H1c4	109.47	C13—C16—H1c16	109.47
C1—C4—H2c4	109.47	C13—C16—H2c16	109.47
C1—C4—H3c4	109.47	C13—C16—H3c16	109.47
H1c4—C4—H2c4	109.47	H1c16—C16—H2c16	109.47
H1c4—C4—H3c4	109.47	H1c16—C16—H3c16	109.47
H2c4—C4—H3c4	109.47	H2c16—C16—H3c16	109.47
Si1—C5—H1c5	109.47	Si2—C17—H1c17	109.47
Si1—C5—H2c5	109.47	Si2—C17—H2c17	109.47
Si1—C5—H3c5	109.47	Si2—C17—H3c17	109.47
H1c5—C5—H2c5	109.47	H1c17—C17—H2c17	109.47
H1c5—C5—H3c5	109.47	H1c17—C17—H3c17	109.47
H2c5—C5—H3c5	109.47	H2c17—C17—H3c17	109.47
Si1—C6—H1c6	109.47	Si2—C18—H1c18	109.47
Si1—C6—H2c6	109.47	Si2—C18—H2c18	109.47
Si1—C6—H3c6	109.47	Si2—C18—H3c18	109.47
H1c6—C6—H2c6	109.47	H1c18—C18—H2c18	109.47
H1c6—C6—H3c6	109.47	H1c18—C18—H3c18	109.47
H2c6—C6—H3c6	109.47	H2c18—C18—H3c18	109.47
Si1—C7—C8	171.0 (2)	Si2—C19—C20	171.3 (3)
C7—C8—C9	177.4 (3)	C19—C20—C21	177.7 (3)
C8—C9—C10	124.7 (3)	C20—C21—C22	124.2 (3)
C8—C9—H1c9	117.66	C20—C21—H1c21	117.92
C10—C9—H1c9	117.66	C22—C21—H1c21	117.92
S1—C10—C9	118.6 (2)	S2—C22—C21	118.4 (2)
S1—C10—C11	119.0 (2)	S2—C22—C23	120.3 (2)
C9—C10—C11	122.4 (2)	C21—C22—C23	121.3 (3)
C10—C11—H1c11	109.47	C22—C23—H1c23	109.47
C10—C11—H2c11	109.47	C22—C23—H2c23	109.47
C10—C11—H3c11	109.47	C22—C23—H3c23	109.47
H1c11—C11—H2c11	109.47	H1c23—C23—H2c23	109.47
H1c11—C11—H3c11	109.47	H1c23—C23—H3c23	109.47
H2c11—C11—H3c11	109.47	H2c23—C23—H3c23	109.47
H1c12—C12—H2c12	109.47	H1c24—C24—H2c24	109.47
H1c12—C12—H3c12	109.47	H1c24—C24—H3c24	109.47
H2c12—C12—H3c12	109.47	H2c24—C24—H3c24	109.47

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