A positive to negative uniaxial thermal expansion crossover in an organic benzothienobenzo­thio­phene structure

Dumitrescu, D.G.; Roche, G.H.; Moreau, J.J.E.; Dautel, O.J.; van der Lee, A.

doi:10.1107/S2052520620007702

A positive to negative uniaxial thermal expansion crossover in an organic benzothienobenzothiophene structure

D. G. Dumitrescu, G. H. Roche, J. J. E. Moreau, O. J. Dautel and A. van der Lee

Compound 6,6′-([1]benzothieno[3,2-b][1]benzothiophene-2,7-diyl)bis(butan-1-ol) (BTBT-C4OH) displays a continuous type 0 first-order isosymmetric phase transition at 200 K which is accompanied by a continuous change of the thermal expansion along the b axis from positive to negative. The equivalent isotropic atomic displacement parameters for all non-hydrogen atoms as well as all the eigenvalues of the anisotropic atomic displacement tensor show discontinuous behavior at the phase transition. The eigenvalues of the translational tensor in a rigid-body description of the molecule are all discontinuous at the phase transition, but the librational eigenvalues are discontinuous only in their temperature derivative. BTBT-C4OH displays a similar type of quasi-supercritical phase transition as bis(hydroxyhexyl)[1]benzothieno[3,2-b][1]benzothiophene (BTBT-C6OH), despite the difference in molecular packing and the very large difference in thermal expansion magnitudes.

Keywords: isosymmetric phase transition; thermal expansion; organic structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620007702/bm5126sup1.cif Contains datablocks global, I, A110, A120, A130, A140, A150, A160, A170, A180, A190, A200, A210, A220, A230, A240, A250, A260, A270, A280, A290, A300
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520620007702/bm5126Isup2.hkl Contains datablock I
	Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620007702/bm5126sup3.pdf Tables S1 and S2. Figures S1-S14

CCDC references: 2008258; 2012245; 2012246; 2012247; 2012248; 2012249; 2012250; 2012251; 2012252; 2012253; 2012254; 2012255; 2012256; 2012257; 2012258; 2012259; 2012260; 2012261; 2012262; 2012263; 2012264

Computing details top

Data collection: Local Elettra software for A110, A120, A130, A140, A150, A160, A170, A180, A190, A200, A210, A220, A230, A240, A250, A260, A270, A280, A290, A300. Cell refinement: XDS (Kabsch, 2010) for A110, A120, A130, A140, A150, A160, A170, A180, A190, A200, A210, A220, A230, A240, A250, A260, A270, A280, A290, A300. Data reduction: XDS (Kabsch, 2010)) for A110, A120, A130, A140, A150, A160, A170, A180, A190, A200, A210, A220, A230, A240, A250, A260, A270, A280, A290, A300. Program(s) used to solve structure: Superflip (Palatinus and Chapuis, 2007 for A110, A120, A130, A140, A150, A160, A170, A180, A190, A200, A210, A220, A230, A240, A250, A260, A270, A280, A290, A300. Program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018) for A110, A120, A130, A140, A150, A160, A170, A180, A190, A200, A210, A220, A230, A240, A250, A260, A270, A280, A290, A300.

(I) top

Crystal data top

C₂₂H₂₄O₂S₂	β = 106.988 (3)°
M_r = 384.56	V = 935.24 (5) Å³
Monoclinic, p12₁/c1	Z = 2.0
Hall symbol: -p 2ybc	D_x = 1.365 Mg m⁻³
a = 13.4387 (4) Å	µ = 0.25 mm⁻¹
b = 5.09342 (10) Å	Stick, colourless
c = 14.2867 (4) Å	0.5 × 0.2 × 0.1 mm

Data collection top

2897 independent reflections	k = →
2897 reflections with F > 0 & F/u(F) > 3.0 & \|F_calc\| > 10⁻³	l = ^→
h = ^→

Refinement top

Least-squares matrix: full	72 constraints
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: HAR
wR(F²) = 0.029	Only H-atom coordinates refined
S = 2.58	Weighting scheme based on measured s.u.'s w = 1/σ(F)
2897 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Special details top

Refinement. . If constraints were applied they are defined by zero eigenvalues of the least-squares hessian, see the value of _refine_ls_SVD_threshold

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

	x	y	z	U_iso*/U_eq
S1	0.647325 (17)	0.32314 (4)	0.537855 (15)	0.02239 (12)
C2	0.64910 (7)	0.55467 (16)	0.62878 (6)	0.0202 (4)
C3	0.55405 (6)	0.69162 (16)	0.61177 (6)	0.0193 (4)
C4	0.48065 (6)	0.59765 (16)	0.52316 (6)	0.0198 (4)
C5	0.54449 (7)	0.88766 (17)	0.67753 (6)	0.0232 (4)
H5	0.4723 (8)	0.9956 (19)	0.6653 (7)	0.027903 (1)*
C6	0.62900 (7)	0.94065 (17)	0.75831 (6)	0.0233 (4)
H6	0.6228 (8)	1.103 (2)	0.8096 (7)	0.028603 (1)*
C7	0.72378 (7)	0.80264 (17)	0.77628 (6)	0.0215 (4)
C8	0.73354 (7)	0.60776 (18)	0.71101 (6)	0.0226 (4)
H8	0.8023 (7)	0.5077 (19)	0.7252 (7)	0.027314 (1)*
C9	0.81196 (7)	0.86099 (18)	0.86716 (6)	0.0235 (4)
H9A	0.8045 (8)	1.0589 (19)	0.8937 (7)	0.028860 (1)*
H9B	0.8864 (8)	0.8645 (18)	0.8516 (7)	0.028860 (1)*
C10	0.81803 (8)	0.66231 (18)	0.94848 (6)	0.0250 (5)
H10A	0.8320 (8)	0.470 (2)	0.9206 (8)	0.030570 (1)*
H10B	0.7439 (8)	0.6643 (19)	0.9611 (7)	0.030570 (1)*
C11	0.90223 (7)	0.72552 (17)	1.04372 (6)	0.0228 (4)
H11A	0.9774 (8)	0.7461 (19)	1.0320 (7)	0.027961 (1)*
H11B	0.8864 (8)	0.9071 (19)	1.0714 (7)	0.027961 (1)*
C12	0.91161 (7)	0.51262 (18)	1.11944 (6)	0.0244 (4)
H12A	0.8398 (7)	0.4893 (19)	1.1358 (7)	0.030085 (1)*
H12B	0.9294 (7)	0.3234 (19)	1.0913 (7)	0.030085 (1)*
O13	0.99092 (5)	0.57593 (13)	1.20706 (4)	0.0276 (3)
H13	1.0025 (10)	0.419 (3)	1.2490 (9)	0.041965 (1)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02104 (10)	0.02602 (13)	0.01892 (12)	0.00299 (8)	0.00397 (8)	−0.00490 (9)
C2	0.0214 (4)	0.0227 (4)	0.0160 (4)	0.0002 (3)	0.0049 (3)	−0.0020 (3)
C3	0.0208 (4)	0.0211 (4)	0.0164 (4)	−0.0006 (3)	0.0061 (3)	−0.0024 (3)
C4	0.0203 (4)	0.0221 (4)	0.0170 (4)	0.0009 (3)	0.0058 (3)	−0.0030 (3)
C5	0.0242 (4)	0.0255 (4)	0.0191 (4)	0.0008 (3)	0.0051 (3)	−0.0053 (3)
C6	0.0260 (4)	0.0248 (4)	0.0182 (4)	−0.0014 (3)	0.0048 (3)	−0.0045 (3)
C7	0.0242 (4)	0.0239 (4)	0.0148 (4)	−0.0037 (3)	0.0031 (3)	−0.0015 (3)
C8	0.0209 (4)	0.0262 (4)	0.0191 (4)	0.0003 (3)	0.0032 (3)	−0.0029 (3)
C9	0.0263 (4)	0.0243 (4)	0.0172 (4)	−0.0054 (3)	0.0020 (3)	−0.0006 (3)
C10	0.0318 (5)	0.0212 (4)	0.0178 (4)	−0.0050 (4)	0.0005 (3)	−0.0006 (3)
C11	0.0288 (4)	0.0195 (4)	0.0169 (4)	−0.0032 (3)	0.0016 (3)	−0.0018 (3)
C12	0.0309 (5)	0.0210 (4)	0.0183 (4)	−0.0014 (3)	0.0024 (4)	−0.0005 (3)
O13	0.0329 (4)	0.0267 (4)	0.0187 (3)	−0.0008 (3)	0.0006 (3)	−0.0015 (3)

Geometric parameters (Å, º) top

S1—C2	1.7495 (8)	C11—C12	1.5107 (12)
O13—C12	1.4238 (10)	C5—H5	1.084 (10)
O13—H13	0.985 (13)	C6—H6	1.124 (10)
C2—C3	1.4128 (11)	C8—H8	1.022 (9)
C2—C8	1.4007 (11)	C9—H9A	1.092 (10)
C3—C4	1.4405 (11)	C9—H9B	1.086 (10)
C3—C5	1.4024 (11)	C10—H10A	1.095 (10)
C5—C6	1.3887 (11)	C10—H10B	1.064 (10)
C6—C7	1.4112 (12)	C11—H11A	1.077 (10)
C7—C8	1.3940 (12)	C11—H11B	1.052 (9)
C7—C9	1.5097 (12)	C12—H12A	1.063 (10)
C9—C10	1.5249 (12)	C12—H12B	1.097 (10)
C10—C11	1.5283 (12)

S1—C2—C3	112.93 (6)	C6—C5—H5	120.8 (5)
S1—C2—C8	125.79 (7)	C7—C6—H6	118.9 (5)
O13—C12—C11	110.57 (7)	C7—C8—H8	118.6 (5)
O13—C12—H12A	109.1 (5)	C7—C9—H9A	110.6 (5)
O13—C12—H12B	109.5 (5)	C7—C9—H9B	111.4 (5)
C12—O13—H13	107.2 (7)	C9—C10—H10A	107.1 (5)
C2—C3—C4	109.85 (7)	C9—C10—H10B	106.2 (5)
C2—C3—C5	119.44 (7)	C10—C9—H9A	109.8 (5)
C2—C8—C7	119.14 (8)	C10—C9—H9B	108.6 (5)
C3—C2—C8	121.28 (7)	C10—C11—H11A	111.5 (5)
C3—C5—C6	118.84 (8)	C10—C11—H11B	110.0 (5)
C4—C3—C5	130.70 (8)	C11—C10—H10A	110.6 (5)
C5—C6—C7	122.00 (8)	C11—C10—H10B	109.5 (5)
C6—C7—C8	119.29 (8)	C11—C12—H12A	110.2 (5)
C6—C7—C9	119.89 (8)	C11—C12—H12B	110.4 (5)
C7—C9—C10	112.23 (7)	C12—C11—H11A	107.2 (5)
C8—C7—C9	120.79 (8)	C12—C11—H11B	110.2 (5)
C9—C10—C11	113.54 (7)	H9A—C9—H9B	103.8 (7)
C10—C11—C12	111.81 (7)	H10A—C10—H10B	109.8 (7)
C2—C8—H8	122.3 (5)	H11A—C11—H11B	106.0 (7)
C3—C5—H5	120.4 (5)	H12A—C12—H12B	107.0 (7)
C5—C6—H6	119.1 (5)

(A110) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.377 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.438 (3) Å	Cell parameters from 7090 reflections
b = 5.061 (1) Å	θ = 2.5–25.0°
c = 14.262 (1) Å	µ = 0.29 mm⁻¹
β = 106.973 (15)°	T = 110 K
V = 927.7 (3) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.025
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8303 measured reflections	h = −19→19
2748 independent reflections	k = −6→6
2488 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0546P)² + 0.561P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2748 reflections	Δρ_max = 0.95 e Å⁻³
121 parameters	Δρ_min = −0.43 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.003 (2)

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
S1	0.64732 (2)	0.32338 (7)	0.53732 (2)	0.02323 (12)
C2	0.64913 (10)	0.5558 (3)	0.62860 (9)	0.0208 (2)
C3	0.55401 (10)	0.6922 (3)	0.61188 (9)	0.0205 (2)
C4	0.48088 (10)	0.5974 (3)	0.52338 (9)	0.0205 (2)
C5	0.54471 (10)	0.8887 (3)	0.67775 (9)	0.0237 (3)
H5	0.481553	0.984169	0.667387	0.028*
C6	0.62896 (10)	0.9416 (3)	0.75822 (9)	0.0244 (3)
H6	0.622742	1.075183	0.802984	0.029*
C7	0.72359 (10)	0.8039 (3)	0.77586 (9)	0.0221 (3)
C8	0.73353 (10)	0.6092 (3)	0.71059 (9)	0.0230 (3)
H8	0.796754	0.513668	0.721522	0.028*
C9	0.81195 (11)	0.8624 (3)	0.86665 (9)	0.0237 (3)
H9A	0.802476	1.041443	0.890683	0.028*
H9B	0.878310	0.861098	0.849668	0.028*
C10	0.81829 (12)	0.6625 (3)	0.94811 (10)	0.0253 (3)
H10A	0.832570	0.485571	0.925332	0.030*
H10B	0.749998	0.654404	0.961293	0.030*
C11	0.90210 (11)	0.7273 (3)	1.04344 (9)	0.0229 (3)
H11A	0.969711	0.750140	1.029769	0.027*
H11B	0.884640	0.896144	1.069977	0.027*
C12	0.91190 (11)	0.5125 (3)	1.11888 (9)	0.0249 (3)
H12A	0.844640	0.489809	1.133243	0.030*
H12B	0.929605	0.343230	1.092803	0.030*
O13	0.99097 (8)	0.5794 (2)	1.20678 (7)	0.0272 (2)
H13	1.0010 (12)	0.456 (4)	1.2441 (12)	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02192 (17)	0.02674 (19)	0.02021 (17)	0.00306 (11)	0.00485 (12)	−0.00497 (11)
C2	0.0238 (6)	0.0218 (6)	0.0179 (5)	−0.0002 (4)	0.0076 (4)	−0.0009 (4)
C3	0.0230 (5)	0.0217 (6)	0.0179 (5)	−0.0015 (4)	0.0075 (4)	−0.0011 (4)
C4	0.0210 (5)	0.0229 (6)	0.0183 (5)	0.0003 (4)	0.0067 (4)	−0.0012 (4)
C5	0.0257 (6)	0.0255 (6)	0.0205 (5)	0.0006 (5)	0.0074 (5)	−0.0039 (5)
C6	0.0293 (6)	0.0247 (6)	0.0195 (5)	−0.0028 (5)	0.0076 (5)	−0.0039 (5)
C7	0.0254 (6)	0.0238 (6)	0.0166 (5)	−0.0049 (5)	0.0053 (4)	0.0003 (4)
C8	0.0231 (6)	0.0258 (6)	0.0197 (5)	−0.0005 (5)	0.0055 (4)	−0.0012 (5)
C9	0.0270 (6)	0.0236 (6)	0.0182 (5)	−0.0054 (5)	0.0030 (4)	−0.0007 (4)
C10	0.0323 (7)	0.0206 (6)	0.0192 (5)	−0.0051 (5)	0.0017 (5)	−0.0003 (4)
C11	0.0292 (6)	0.0192 (6)	0.0180 (5)	−0.0032 (5)	0.0034 (4)	−0.0009 (4)
C12	0.0318 (6)	0.0212 (6)	0.0187 (5)	−0.0024 (5)	0.0025 (5)	−0.0007 (5)
O13	0.0334 (5)	0.0247 (5)	0.0187 (4)	−0.0013 (4)	0.0001 (4)	0.0003 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7342 (13)	C9—C10	1.5241 (19)
S1—C2	1.7496 (13)	C9—H9A	0.9900
C2—C8	1.3972 (17)	C9—H9B	0.9900
C2—C3	1.4104 (18)	C10—C11	1.5267 (18)
C3—C5	1.3983 (18)	C10—H10A	0.9900
C3—C4	1.4369 (17)	C10—H10B	0.9900
C4—C4ⁱ	1.372 (2)	C11—C12	1.5083 (19)
C5—C6	1.3828 (18)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.4069 (19)	C12—O13	1.4274 (16)
C6—H6	0.9500	C12—H12A	0.9900
C7—C8	1.3887 (19)	C12—H12B	0.9900
C7—C9	1.5088 (18)	O13—H13	0.81 (2)
C8—H8	0.9500

C4ⁱ—S1—C2	90.69 (6)	C10—C9—H9A	109.2
C8—C2—C3	121.41 (12)	C7—C9—H9B	109.2
C8—C2—S1	125.75 (10)	C10—C9—H9B	109.2
C3—C2—S1	112.84 (9)	H9A—C9—H9B	107.9
C5—C3—C2	119.26 (12)	C9—C10—C11	113.49 (11)
C5—C3—C4	130.94 (12)	C9—C10—H10A	108.9
C2—C3—C4	109.80 (11)	C11—C10—H10A	108.9
C4ⁱ—C4—C3	114.20 (14)	C9—C10—H10B	108.9
C4ⁱ—C4—S1ⁱ	112.46 (13)	C11—C10—H10B	108.9
C3—C4—S1ⁱ	133.34 (10)	H10A—C10—H10B	107.7
C6—C5—C3	118.90 (12)	C12—C11—C10	111.61 (11)
C6—C5—H5	120.5	C12—C11—H11A	109.3
C3—C5—H5	120.5	C10—C11—H11A	109.3
C5—C6—C7	122.05 (12)	C12—C11—H11B	109.3
C5—C6—H6	119.0	C10—C11—H11B	109.3
C7—C6—H6	119.0	H11A—C11—H11B	108.0
C8—C7—C6	119.37 (12)	O13—C12—C11	110.06 (11)
C8—C7—C9	120.59 (12)	O13—C12—H12A	109.6
C6—C7—C9	120.01 (12)	C11—C12—H12A	109.6
C7—C8—C2	119.00 (12)	O13—C12—H12B	109.6
C7—C8—H8	120.5	C11—C12—H12B	109.6
C2—C8—H8	120.5	H12A—C12—H12B	108.2
C7—C9—C10	112.26 (11)	C12—O13—H13	109.5
C7—C9—H9A	109.2

C4ⁱ—S1—C2—C8	179.45 (12)	C3—C5—C6—C7	−0.1 (2)
C4ⁱ—S1—C2—C3	−0.70 (10)	C5—C6—C7—C8	0.3 (2)
C8—C2—C3—C5	1.29 (19)	C5—C6—C7—C9	−177.82 (12)
S1—C2—C3—C5	−178.57 (10)	C6—C7—C8—C2	0.3 (2)
C8—C2—C3—C4	−179.51 (12)	C9—C7—C8—C2	178.37 (12)
S1—C2—C3—C4	0.64 (14)	C3—C2—C8—C7	−1.1 (2)
C5—C3—C4—C4ⁱ	178.88 (15)	S1—C2—C8—C7	178.76 (10)
C2—C3—C4—C4ⁱ	−0.20 (19)	C8—C7—C9—C10	−79.29 (16)
C5—C3—C4—S1ⁱ	−1.5 (2)	C6—C7—C9—C10	98.78 (15)
C2—C3—C4—S1ⁱ	179.39 (11)	C7—C9—C10—C11	−175.92 (12)
C2—C3—C5—C6	−0.7 (2)	C9—C10—C11—C12	−175.02 (12)
C4—C3—C5—C6	−179.71 (13)	C10—C11—C12—O13	179.86 (11)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.81	2.02	2.7942 (9)	160
C6—H6···S1ⁱⁱⁱ	0.95	3.30	4.0922 (13)	142
C9—H9A···S1ⁱⁱⁱ	0.99	3.43	4.0609 (15)	124
C10—H10B···S1ⁱⁱⁱ	0.99	3.31	3.9212 (16)	122
C10—H10B···S1^iv	0.99	3.13	3.8276 (15)	129
C11—H11B···S1ⁱⁱⁱ	0.99	3.40	4.0897 (16)	129
C12—H12A···S1^iv	0.99	3.05	3.8037 (16)	134

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A120) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.450 (3) Å	Cell parameters from 6962 reflections
b = 5.063 (1) Å	θ = 2.3–24.3°
c = 14.270 (1) Å	µ = 0.29 mm⁻¹
β = 107.026 (15)°	T = 120 K
V = 929.2 (3) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.023
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8199 measured reflections	h = −19→19
2739 independent reflections	k = −6→6
2497 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0565P)² + 0.4952P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2739 reflections	Δρ_max = 0.93 e Å⁻³
121 parameters	Δρ_min = −0.45 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.003 (3)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64721 (2)	0.32336 (7)	0.53739 (2)	0.02441 (12)
C2	0.64899 (10)	0.5559 (3)	0.62858 (9)	0.0218 (2)
C3	0.55402 (10)	0.6920 (3)	0.61191 (9)	0.0216 (2)
C4	0.48089 (9)	0.5974 (3)	0.52340 (9)	0.0216 (2)
C5	0.54474 (10)	0.8884 (3)	0.67769 (9)	0.0250 (3)
H5	0.481631	0.983903	0.667235	0.030*
C6	0.62895 (10)	0.9413 (3)	0.75828 (9)	0.0255 (3)
H6	0.622717	1.074594	0.803094	0.031*
C7	0.72360 (10)	0.8037 (3)	0.77586 (9)	0.0233 (3)
C8	0.73341 (10)	0.6090 (3)	0.71070 (9)	0.0241 (3)
H8	0.796540	0.513274	0.721708	0.029*
C9	0.81190 (11)	0.8620 (3)	0.86678 (9)	0.0249 (3)
H9A	0.802437	1.040962	0.890785	0.030*
H9B	0.878236	0.860707	0.849881	0.030*
C10	0.81827 (12)	0.6623 (3)	0.94816 (10)	0.0265 (3)
H10A	0.832527	0.485499	0.925423	0.032*
H10B	0.750029	0.654314	0.961301	0.032*
C11	0.90204 (11)	0.7272 (3)	1.04349 (9)	0.0241 (3)
H11A	0.969603	0.749838	1.029867	0.029*
H11B	0.884625	0.896039	1.069954	0.029*
C12	0.91182 (11)	0.5128 (3)	1.11892 (9)	0.0262 (3)
H12A	0.844620	0.490403	1.133263	0.031*
H12B	0.929413	0.343493	1.092882	0.031*
O13	0.99087 (8)	0.5794 (2)	1.20676 (7)	0.0286 (2)
H13	1.0000 (12)	0.457 (4)	1.2444 (12)	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02290 (17)	0.0281 (2)	0.02137 (17)	0.00317 (11)	0.00508 (12)	−0.00530 (11)
C2	0.0246 (6)	0.0229 (6)	0.0187 (5)	−0.0005 (4)	0.0078 (4)	−0.0010 (4)
C3	0.0244 (5)	0.0225 (6)	0.0188 (5)	−0.0015 (4)	0.0078 (4)	−0.0009 (4)
C4	0.0217 (5)	0.0240 (6)	0.0195 (5)	0.0005 (4)	0.0068 (4)	−0.0008 (4)
C5	0.0273 (6)	0.0266 (6)	0.0214 (6)	0.0006 (5)	0.0077 (5)	−0.0041 (5)
C6	0.0305 (6)	0.0260 (6)	0.0204 (5)	−0.0028 (5)	0.0079 (5)	−0.0037 (5)
C7	0.0267 (6)	0.0251 (6)	0.0175 (5)	−0.0051 (5)	0.0055 (4)	0.0002 (4)
C8	0.0241 (6)	0.0270 (6)	0.0207 (5)	−0.0006 (5)	0.0056 (4)	−0.0014 (5)
C9	0.0285 (6)	0.0250 (6)	0.0188 (5)	−0.0058 (5)	0.0033 (4)	−0.0007 (4)
C10	0.0338 (7)	0.0213 (6)	0.0204 (5)	−0.0056 (5)	0.0016 (5)	−0.0001 (4)
C11	0.0304 (6)	0.0204 (6)	0.0189 (5)	−0.0034 (5)	0.0032 (5)	−0.0010 (4)
C12	0.0330 (6)	0.0225 (6)	0.0195 (5)	−0.0025 (5)	0.0021 (5)	−0.0004 (5)
O13	0.0351 (5)	0.0259 (5)	0.0196 (4)	−0.0011 (4)	−0.0001 (4)	0.0006 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7340 (13)	C9—C10	1.5231 (19)
S1—C2	1.7497 (13)	C9—H9A	0.9900
C2—C8	1.3985 (17)	C9—H9B	0.9900
C2—C3	1.4090 (18)	C10—C11	1.5265 (18)
C3—C5	1.3977 (18)	C10—H10A	0.9900
C3—C4	1.4368 (17)	C10—H10B	0.9900
C4—C4ⁱ	1.373 (2)	C11—C12	1.5072 (19)
C5—C6	1.3837 (18)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.408 (2)	C12—O13	1.4265 (15)
C6—H6	0.9500	C12—H12A	0.9900
C7—C8	1.3876 (19)	C12—H12B	0.9900
C7—C9	1.5095 (18)	O13—H13	0.80 (2)
C8—H8	0.9500

C4ⁱ—S1—C2	90.67 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.39 (12)	C7—C9—H9B	109.1
C8—C2—S1	125.70 (10)	C10—C9—H9B	109.1
C3—C2—S1	112.91 (9)	H9A—C9—H9B	107.9
C5—C3—C2	119.30 (12)	C9—C10—C11	113.50 (11)
C5—C3—C4	130.89 (12)	C9—C10—H10A	108.9
C2—C3—C4	109.80 (11)	C11—C10—H10A	108.9
C4ⁱ—C4—C3	114.18 (14)	C9—C10—H10B	108.9
C4ⁱ—C4—S1ⁱ	112.43 (13)	C11—C10—H10B	108.9
C3—C4—S1ⁱ	133.39 (10)	H10A—C10—H10B	107.7
C6—C5—C3	118.93 (13)	C12—C11—C10	111.64 (11)
C6—C5—H5	120.5	C12—C11—H11A	109.3
C3—C5—H5	120.5	C10—C11—H11A	109.3
C5—C6—C7	121.97 (12)	C12—C11—H11B	109.3
C5—C6—H6	119.0	C10—C11—H11B	109.3
C7—C6—H6	119.0	H11A—C11—H11B	108.0
C8—C7—C6	119.39 (12)	O13—C12—C11	110.12 (11)
C8—C7—C9	120.63 (13)	O13—C12—H12A	109.6
C6—C7—C9	119.95 (12)	C11—C12—H12A	109.6
C7—C8—C2	119.01 (12)	O13—C12—H12B	109.6
C7—C8—H8	120.5	C11—C12—H12B	109.6
C2—C8—H8	120.5	H12A—C12—H12B	108.2
C7—C9—C10	112.34 (11)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.39 (12)	C3—C5—C6—C7	0.1 (2)
C4ⁱ—S1—C2—C3	−0.62 (10)	C5—C6—C7—C8	0.1 (2)
C8—C2—C3—C5	1.43 (19)	C5—C6—C7—C9	−177.79 (12)
S1—C2—C3—C5	−178.56 (10)	C6—C7—C8—C2	0.5 (2)
C8—C2—C3—C4	−179.46 (12)	C9—C7—C8—C2	178.35 (12)
S1—C2—C3—C4	0.55 (14)	C3—C2—C8—C7	−1.3 (2)
C5—C3—C4—C4ⁱ	178.82 (15)	S1—C2—C8—C7	178.73 (10)
C2—C3—C4—C4ⁱ	−0.15 (19)	C8—C7—C9—C10	−79.19 (16)
C5—C3—C4—S1ⁱ	−1.6 (2)	C6—C7—C9—C10	98.66 (15)
C2—C3—C4—S1ⁱ	179.45 (11)	C7—C9—C10—C11	−175.94 (12)
C2—C3—C5—C6	−0.8 (2)	C9—C10—C11—C12	−175.06 (12)
C4—C3—C5—C6	−179.71 (13)	C10—C11—C12—O13	179.82 (12)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.80	2.03	2.7954 (9)	160
C6—H6···S1ⁱⁱⁱ	0.95	3.30	4.0951 (13)	142
C9—H9A···S1ⁱⁱⁱ	0.99	3.43	4.0657 (15)	124
C10—H10B···S1ⁱⁱⁱ	0.99	3.31	3.9257 (17)	122
C10—H10B···S1^iv	0.99	3.13	3.8312 (15)	129
C11—H11B···S1ⁱⁱⁱ	0.99	3.40	4.0937 (16)	129
C12—H12A···S1^iv	0.99	3.05	3.8068 (16)	134

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A130) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.462 (2) Å	Cell parameters from 6972 reflections
b = 5.064 (1) Å	θ = 2.5–24.8°
c = 14.278 (1) Å	µ = 0.29 mm⁻¹
β = 107.080 (14)°	T = 130 K
V = 930.4 (2) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.023
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8277 measured reflections	h = −19→19
2748 independent reflections	k = −6→7
2496 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0566P)² + 0.4659P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2748 reflections	Δρ_max = 0.91 e Å⁻³
121 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.003 (3)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64710 (2)	0.32342 (7)	0.53747 (2)	0.02573 (12)
C2	0.64890 (10)	0.5559 (3)	0.62866 (9)	0.0228 (2)
C3	0.55395 (10)	0.6919 (3)	0.61190 (9)	0.0225 (2)
C4	0.48091 (9)	0.5975 (3)	0.52342 (9)	0.0227 (2)
C5	0.54472 (10)	0.8881 (3)	0.67773 (9)	0.0262 (3)
H5	0.481635	0.983473	0.667335	0.031*
C6	0.62893 (10)	0.9410 (3)	0.75825 (9)	0.0267 (3)
H6	0.622760	1.074441	0.802976	0.032*
C7	0.72350 (10)	0.8033 (3)	0.77597 (9)	0.0245 (3)
C8	0.73327 (10)	0.6088 (3)	0.71080 (9)	0.0253 (3)
H8	0.796337	0.512999	0.721826	0.030*
C9	0.81171 (11)	0.8618 (3)	0.86675 (9)	0.0263 (3)
H9A	0.802211	1.040754	0.890704	0.032*
H9B	0.877968	0.860599	0.849875	0.032*
C10	0.81821 (12)	0.6623 (3)	0.94819 (10)	0.0280 (3)
H10A	0.750034	0.654191	0.961321	0.034*
H10B	0.832454	0.485443	0.925490	0.034*
C11	0.90197 (11)	0.7272 (3)	1.04349 (9)	0.0254 (3)
H11A	0.969474	0.749858	1.029905	0.030*
H11B	0.884575	0.895995	1.069950	0.030*
C12	0.91174 (11)	0.5127 (3)	1.11885 (9)	0.0275 (3)
H12A	0.844589	0.490238	1.133143	0.033*
H12B	0.929337	0.343453	1.092833	0.033*
O13	0.99080 (8)	0.5795 (2)	1.20673 (7)	0.0302 (2)
H13	1.0001 (12)	0.457 (4)	1.2443 (12)	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02391 (17)	0.0298 (2)	0.02238 (17)	0.00335 (11)	0.00504 (12)	−0.00564 (11)
C2	0.0257 (5)	0.0242 (6)	0.0191 (5)	−0.0005 (4)	0.0075 (4)	−0.0009 (4)
C3	0.0251 (5)	0.0238 (6)	0.0195 (5)	−0.0015 (4)	0.0080 (4)	−0.0010 (4)
C4	0.0229 (5)	0.0255 (6)	0.0200 (5)	0.0004 (4)	0.0068 (4)	−0.0010 (4)
C5	0.0280 (6)	0.0282 (6)	0.0225 (5)	0.0006 (5)	0.0075 (5)	−0.0043 (5)
C6	0.0317 (6)	0.0268 (6)	0.0216 (5)	−0.0031 (5)	0.0078 (5)	−0.0041 (5)
C7	0.0277 (6)	0.0263 (6)	0.0185 (5)	−0.0055 (5)	0.0052 (4)	0.0001 (4)
C8	0.0254 (6)	0.0281 (6)	0.0215 (5)	−0.0010 (5)	0.0057 (4)	−0.0016 (5)
C9	0.0297 (6)	0.0260 (6)	0.0204 (5)	−0.0065 (5)	0.0032 (4)	−0.0010 (4)
C10	0.0359 (7)	0.0224 (6)	0.0211 (5)	−0.0060 (5)	0.0013 (5)	−0.0003 (4)
C11	0.0318 (6)	0.0219 (6)	0.0197 (5)	−0.0038 (5)	0.0032 (5)	−0.0012 (4)
C12	0.0345 (6)	0.0234 (6)	0.0207 (5)	−0.0025 (5)	0.0022 (5)	−0.0008 (5)
O13	0.0370 (5)	0.0272 (5)	0.0206 (4)	−0.0012 (4)	−0.0005 (4)	0.0003 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7337 (13)	C9—C10	1.5235 (18)
S1—C2	1.7503 (13)	C9—H9A	0.9900
C2—C8	1.3981 (17)	C9—H9B	0.9900
C2—C3	1.4090 (18)	C10—C11	1.5264 (18)
C3—C5	1.3982 (17)	C10—H10A	0.9900
C3—C4	1.4358 (17)	C10—H10B	0.9900
C4—C4ⁱ	1.375 (2)	C11—C12	1.5075 (18)
C5—C6	1.3831 (18)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.4079 (19)	C12—O13	1.4273 (15)
C6—H6	0.9500	C12—H12A	0.9900
C7—C8	1.3874 (18)	C12—H12B	0.9900
C7—C9	1.5079 (18)	O13—H13	0.80 (2)
C8—H8	0.9500

C4ⁱ—S1—C2	90.70 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.45 (12)	C7—C9—H9B	109.1
C8—C2—S1	125.68 (10)	C10—C9—H9B	109.1
C3—C2—S1	112.87 (9)	H9A—C9—H9B	107.9
C5—C3—C2	119.23 (12)	C11—C10—C9	113.53 (11)
C5—C3—C4	130.91 (12)	C11—C10—H10A	108.9
C2—C3—C4	109.85 (11)	C9—C10—H10A	108.9
C4ⁱ—C4—C3	114.19 (14)	C11—C10—H10B	108.9
C4ⁱ—C4—S1ⁱ	112.38 (12)	C9—C10—H10B	108.9
C3—C4—S1ⁱ	133.43 (10)	H10A—C10—H10B	107.7
C6—C5—C3	118.91 (12)	C12—C11—C10	111.58 (11)
C6—C5—H5	120.5	C12—C11—H11A	109.3
C3—C5—H5	120.5	C10—C11—H11A	109.3
C5—C6—C7	122.05 (12)	C12—C11—H11B	109.3
C5—C6—H6	119.0	C10—C11—H11B	109.3
C7—C6—H6	119.0	H11A—C11—H11B	108.0
C8—C7—C6	119.33 (12)	O13—C12—C11	110.05 (11)
C8—C7—C9	120.68 (12)	O13—C12—H12A	109.7
C6—C7—C9	119.96 (12)	C11—C12—H12A	109.7
C7—C8—C2	119.01 (12)	O13—C12—H12B	109.7
C7—C8—H8	120.5	C11—C12—H12B	109.7
C2—C8—H8	120.5	H12A—C12—H12B	108.2
C7—C9—C10	112.33 (11)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.34 (12)	C3—C5—C6—C7	−0.1 (2)
C4ⁱ—S1—C2—C3	−0.60 (10)	C5—C6—C7—C8	0.2 (2)
C8—C2—C3—C5	1.46 (19)	C5—C6—C7—C9	−177.81 (12)
S1—C2—C3—C5	−178.59 (10)	C6—C7—C8—C2	0.45 (19)
C8—C2—C3—C4	−179.45 (12)	C9—C7—C8—C2	178.48 (12)
S1—C2—C3—C4	0.50 (14)	C3—C2—C8—C7	−1.3 (2)
C5—C3—C4—C4ⁱ	178.87 (15)	S1—C2—C8—C7	178.76 (10)
C2—C3—C4—C4ⁱ	−0.09 (19)	C8—C7—C9—C10	−79.25 (16)
C5—C3—C4—S1ⁱ	−1.6 (2)	C6—C7—C9—C10	98.77 (15)
C2—C3—C4—S1ⁱ	179.45 (11)	C7—C9—C10—C11	−175.96 (12)
C2—C3—C5—C6	−0.8 (2)	C9—C10—C11—C12	−175.06 (12)
C4—C3—C5—C6	−179.62 (13)	C10—C11—C12—O13	179.84 (12)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.80	2.03	2.7963 (9)	160
C6—H6···S1ⁱⁱⁱ	0.95	3.31	4.0993 (13)	142
C9—H9A···S1ⁱⁱⁱ	0.99	3.43	4.0700 (15)	124
C10—H10A···S1ⁱⁱⁱ	0.99	3.31	3.9292 (16)	122
C10—H10A···S1^iv	0.99	3.14	3.8346 (15)	129
C11—H11B···S1ⁱⁱⁱ	0.99	3.40	4.0968 (15)	129
C12—H12A···S1^iv	0.99	3.05	3.8088 (15)	134

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A140) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.371 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.473 (2) Å	Cell parameters from 6963 reflections
b = 5.066 (1) Å	θ = 2.4–26.0°
c = 14.286 (1) Å	µ = 0.29 mm⁻¹
β = 107.137 (14)°	T = 140 K
V = 931.8 (2) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.024
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8296 measured reflections	h = −19→19
2749 independent reflections	k = −6→7
2484 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0541P)² + 0.465P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2749 reflections	Δρ_max = 0.91 e Å⁻³
121 parameters	Δρ_min = −0.37 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.004 (2)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64700 (2)	0.32344 (7)	0.53754 (2)	0.02705 (12)
C2	0.64886 (10)	0.5556 (3)	0.62875 (9)	0.0239 (2)
C3	0.55395 (10)	0.6918 (3)	0.61189 (9)	0.0235 (2)
C4	0.48091 (9)	0.5972 (3)	0.52336 (9)	0.0235 (2)
C5	0.54474 (11)	0.8876 (3)	0.67773 (9)	0.0274 (3)
H5	0.481678	0.982818	0.667359	0.033*
C6	0.62892 (11)	0.9404 (3)	0.75822 (9)	0.0281 (3)
H6	0.622778	1.073735	0.802955	0.034*
C7	0.72340 (10)	0.8029 (3)	0.77594 (9)	0.0257 (3)
C8	0.73318 (10)	0.6089 (3)	0.71079 (9)	0.0264 (3)
H8	0.796292	0.513485	0.721769	0.032*
C9	0.81155 (11)	0.8615 (3)	0.86684 (9)	0.0276 (3)
H9A	0.802019	1.040429	0.890726	0.033*
H9B	0.877798	0.860396	0.850058	0.033*
C10	0.81808 (12)	0.6622 (3)	0.94826 (10)	0.0295 (3)
H10A	0.749971	0.654316	0.961379	0.035*
H10B	0.832242	0.485408	0.925585	0.035*
C11	0.90186 (11)	0.7270 (3)	1.04354 (9)	0.0267 (3)
H11A	0.969306	0.749398	1.029962	0.032*
H11B	0.884566	0.895816	1.069948	0.032*
C12	0.91168 (11)	0.5130 (3)	1.11892 (9)	0.0289 (3)
H12A	0.844583	0.490746	1.133199	0.035*
H12B	0.929181	0.343694	1.092955	0.035*
O13	0.99072 (8)	0.5796 (2)	1.20674 (7)	0.0319 (2)
H13	1.0002 (13)	0.457 (4)	1.2441 (13)	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02489 (17)	0.0314 (2)	0.02349 (17)	0.00360 (11)	0.00509 (12)	−0.00586 (11)
C2	0.0270 (6)	0.0253 (6)	0.0202 (5)	−0.0005 (5)	0.0080 (4)	−0.0010 (4)
C3	0.0262 (6)	0.0252 (6)	0.0199 (5)	−0.0014 (4)	0.0079 (4)	−0.0008 (4)
C4	0.0237 (5)	0.0264 (6)	0.0208 (5)	0.0004 (4)	0.0071 (4)	−0.0013 (4)
C5	0.0291 (6)	0.0295 (6)	0.0238 (6)	0.0004 (5)	0.0080 (5)	−0.0046 (5)
C6	0.0337 (6)	0.0285 (6)	0.0221 (5)	−0.0031 (5)	0.0083 (5)	−0.0045 (5)
C7	0.0289 (6)	0.0278 (6)	0.0192 (5)	−0.0061 (5)	0.0054 (4)	0.0002 (4)
C8	0.0261 (6)	0.0297 (6)	0.0225 (5)	−0.0012 (5)	0.0057 (4)	−0.0014 (5)
C9	0.0312 (6)	0.0276 (6)	0.0210 (5)	−0.0067 (5)	0.0030 (5)	−0.0010 (5)
C10	0.0375 (7)	0.0237 (6)	0.0223 (6)	−0.0061 (5)	0.0010 (5)	−0.0004 (4)
C11	0.0329 (6)	0.0231 (6)	0.0209 (5)	−0.0039 (5)	0.0031 (5)	−0.0016 (4)
C12	0.0365 (7)	0.0249 (6)	0.0211 (5)	−0.0029 (5)	0.0019 (5)	−0.0008 (5)
O13	0.0388 (5)	0.0289 (5)	0.0218 (4)	−0.0014 (4)	−0.0009 (4)	0.0001 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7333 (13)	C9—C10	1.5233 (19)
S1—C2	1.7501 (13)	C9—H9A	0.9900
C2—C8	1.3972 (17)	C9—H9B	0.9900
C2—C3	1.4099 (18)	C10—C11	1.5260 (18)
C3—C5	1.3973 (18)	C10—H10A	0.9900
C3—C4	1.4366 (17)	C10—H10B	0.9900
C4—C4ⁱ	1.372 (2)	C11—C12	1.5062 (19)
C5—C6	1.3826 (18)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.407 (2)	C12—O13	1.4265 (16)
C6—H6	0.9500	C12—H12A	0.9900
C7—C8	1.3865 (19)	C12—H12B	0.9900
C7—C9	1.5086 (18)	O13—H13	0.80 (2)
C8—H8	0.9500

C4ⁱ—S1—C2	90.68 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.41 (12)	C7—C9—H9B	109.1
C8—C2—S1	125.74 (10)	C10—C9—H9B	109.1
C3—C2—S1	112.85 (9)	H9A—C9—H9B	107.9
C5—C3—C2	119.22 (12)	C11—C10—C9	113.56 (11)
C5—C3—C4	130.97 (12)	C11—C10—H10A	108.9
C2—C3—C4	109.80 (11)	C9—C10—H10A	108.9
C4ⁱ—C4—C3	114.20 (14)	C11—C10—H10B	108.9
C4ⁱ—C4—S1ⁱ	112.46 (13)	C9—C10—H10B	108.9
C3—C4—S1ⁱ	133.34 (10)	H10A—C10—H10B	107.7
C6—C5—C3	118.92 (13)	C12—C11—C10	111.65 (11)
C6—C5—H5	120.5	C12—C11—H11A	109.3
C3—C5—H5	120.5	C10—C11—H11A	109.3
C5—C6—C7	122.05 (12)	C12—C11—H11B	109.3
C5—C6—H6	119.0	C10—C11—H11B	109.3
C7—C6—H6	119.0	H11A—C11—H11B	108.0
C8—C7—C6	119.35 (12)	O13—C12—C11	110.12 (11)
C8—C7—C9	120.73 (13)	O13—C12—H12A	109.6
C6—C7—C9	119.90 (12)	C11—C12—H12A	109.6
C7—C8—C2	119.04 (12)	O13—C12—H12B	109.6
C7—C8—H8	120.5	C11—C12—H12B	109.6
C2—C8—H8	120.5	H12A—C12—H12B	108.2
C7—C9—C10	112.36 (11)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.52 (13)	C3—C5—C6—C7	−0.1 (2)
C4ⁱ—S1—C2—C3	−0.65 (10)	C5—C6—C7—C8	0.3 (2)
C8—C2—C3—C5	1.2 (2)	C5—C6—C7—C9	−177.79 (13)
S1—C2—C3—C5	−178.64 (10)	C6—C7—C8—C2	0.3 (2)
C8—C2—C3—C4	−179.54 (12)	C9—C7—C8—C2	178.35 (12)
S1—C2—C3—C4	0.62 (14)	C3—C2—C8—C7	−1.0 (2)
C5—C3—C4—C4ⁱ	178.91 (15)	S1—C2—C8—C7	178.78 (10)
C2—C3—C4—C4ⁱ	−0.24 (19)	C8—C7—C9—C10	−79.32 (17)
C5—C3—C4—S1ⁱ	−1.4 (2)	C6—C7—C9—C10	98.72 (16)
C2—C3—C4—S1ⁱ	179.44 (11)	C7—C9—C10—C11	−176.06 (12)
C2—C3—C5—C6	−0.6 (2)	C9—C10—C11—C12	−175.08 (12)
C4—C3—C5—C6	−179.68 (13)	C10—C11—C12—O13	179.84 (12)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.80	2.03	2.7972 (10)	160
C6—H6···S1ⁱⁱⁱ	0.95	3.31	4.1037 (13)	142
C9—H9A···S1ⁱⁱⁱ	0.99	3.44	4.0738 (16)	124
C10—H10A···S1ⁱⁱⁱ	0.99	3.32	3.9321 (17)	122
C10—H10A···S1^iv	0.99	3.14	3.8373 (15)	129
C11—H11B···S1ⁱⁱⁱ	0.99	3.41	4.1003 (16)	129
C12—H12A···S1^iv	0.99	3.06	3.8117 (15)	134

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A150) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.369 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.484 (2) Å	Cell parameters from 6940 reflections
b = 5.068 (1) Å	θ = 2.4–24.9°
c = 14.294 (1) Å	µ = 0.29 mm⁻¹
β = 107.194 (12)°	T = 150 K
V = 933.2 (2) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.023
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8300 measured reflections	h = −19→19
2741 independent reflections	k = −6→7
2472 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0552P)² + 0.473P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2741 reflections	Δρ_max = 0.87 e Å⁻³
121 parameters	Δρ_min = −0.38 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.004 (3)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64689 (2)	0.32342 (7)	0.53763 (2)	0.02843 (12)
C2	0.64878 (10)	0.5555 (3)	0.62876 (9)	0.0249 (2)
C3	0.55399 (10)	0.6915 (3)	0.61196 (9)	0.0246 (2)
C4	0.48093 (10)	0.5971 (3)	0.52333 (9)	0.0246 (2)
C5	0.54480 (11)	0.8872 (3)	0.67774 (10)	0.0287 (3)
H5	0.481761	0.982410	0.667308	0.034*
C6	0.62893 (11)	0.9401 (3)	0.75826 (9)	0.0293 (3)
H6	0.622804	1.073344	0.802980	0.035*
C7	0.72333 (11)	0.8026 (3)	0.77600 (9)	0.0269 (3)
C8	0.73313 (10)	0.6085 (3)	0.71084 (10)	0.0277 (3)
H8	0.796186	0.513039	0.721856	0.033*
C9	0.81154 (11)	0.8612 (3)	0.86693 (10)	0.0292 (3)
H9A	0.802090	1.040047	0.890790	0.035*
H9B	0.877727	0.859826	0.850182	0.035*
C10	0.81806 (12)	0.6623 (3)	0.94825 (10)	0.0308 (3)
H10A	0.749996	0.654588	0.961332	0.037*
H10B	0.832125	0.485486	0.925599	0.037*
C11	0.90190 (11)	0.7269 (3)	1.04359 (9)	0.0280 (3)
H11A	0.969310	0.748952	1.030062	0.034*
H11B	0.884725	0.895815	1.069944	0.034*
C12	0.91162 (12)	0.5132 (3)	1.11898 (10)	0.0304 (3)
H12A	0.844545	0.491266	1.133178	0.037*
H12B	0.929044	0.343871	1.093085	0.037*
O13	0.99058 (9)	0.5797 (2)	1.20677 (7)	0.0336 (2)
H13	1.0001 (13)	0.455 (4)	1.2448 (13)	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02608 (18)	0.0330 (2)	0.02467 (18)	0.00379 (12)	0.00520 (12)	−0.00617 (12)
C2	0.0280 (6)	0.0263 (6)	0.0211 (5)	−0.0006 (5)	0.0082 (4)	−0.0011 (4)
C3	0.0266 (6)	0.0267 (6)	0.0211 (5)	−0.0016 (4)	0.0081 (4)	−0.0009 (4)
C4	0.0246 (5)	0.0276 (6)	0.0217 (5)	0.0002 (5)	0.0072 (4)	−0.0013 (5)
C5	0.0307 (6)	0.0310 (7)	0.0246 (6)	0.0007 (5)	0.0083 (5)	−0.0049 (5)
C6	0.0347 (7)	0.0297 (7)	0.0232 (6)	−0.0029 (5)	0.0083 (5)	−0.0045 (5)
C7	0.0304 (6)	0.0290 (7)	0.0200 (5)	−0.0061 (5)	0.0055 (5)	0.0000 (4)
C8	0.0272 (6)	0.0308 (7)	0.0241 (6)	−0.0013 (5)	0.0060 (5)	−0.0017 (5)
C9	0.0331 (6)	0.0289 (7)	0.0222 (5)	−0.0073 (5)	0.0030 (5)	−0.0009 (5)
C10	0.0387 (7)	0.0250 (6)	0.0233 (6)	−0.0067 (5)	0.0008 (5)	−0.0005 (5)
C11	0.0343 (6)	0.0241 (6)	0.0223 (5)	−0.0041 (5)	0.0030 (5)	−0.0017 (5)
C12	0.0385 (7)	0.0257 (6)	0.0225 (6)	−0.0028 (5)	0.0019 (5)	−0.0008 (5)
O13	0.0407 (6)	0.0306 (5)	0.0227 (4)	−0.0015 (4)	−0.0011 (4)	0.0001 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7332 (13)	C9—C10	1.5214 (19)
S1—C2	1.7495 (13)	C9—H9A	0.9900
C2—C8	1.3976 (18)	C9—H9B	0.9900
C2—C3	1.4090 (18)	C10—C11	1.5269 (18)
C3—C5	1.3971 (18)	C10—H10A	0.9900
C3—C4	1.4375 (17)	C10—H10B	0.9900
C4—C4ⁱ	1.372 (3)	C11—C12	1.5059 (19)
C5—C6	1.3826 (18)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.407 (2)	C12—O13	1.4254 (16)
C6—H6	0.9500	C12—H12A	0.9900
C7—C8	1.3879 (19)	C12—H12B	0.9900
C7—C9	1.5093 (18)	O13—H13	0.82 (2)
C8—H8	0.9500

C4ⁱ—S1—C2	90.66 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.41 (12)	C7—C9—H9B	109.1
C8—C2—S1	125.68 (10)	C10—C9—H9B	109.1
C3—C2—S1	112.91 (9)	H9A—C9—H9B	107.9
C5—C3—C2	119.28 (12)	C11—C10—C9	113.59 (11)
C5—C3—C4	130.95 (12)	C11—C10—H10A	108.8
C2—C3—C4	109.76 (11)	C9—C10—H10A	108.8
C4ⁱ—C4—C3	114.18 (14)	C11—C10—H10B	108.8
C4ⁱ—C4—S1ⁱ	112.48 (13)	C9—C10—H10B	108.8
C3—C4—S1ⁱ	133.34 (10)	H10A—C10—H10B	107.7
C6—C5—C3	118.93 (13)	C12—C11—C10	111.68 (11)
C6—C5—H5	120.5	C12—C11—H11A	109.3
C3—C5—H5	120.5	C10—C11—H11A	109.3
C5—C6—C7	122.01 (13)	C12—C11—H11B	109.3
C5—C6—H6	119.0	C10—C11—H11B	109.3
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.39 (12)	O13—C12—C11	110.15 (12)
C8—C7—C9	120.67 (13)	O13—C12—H12A	109.6
C6—C7—C9	119.91 (12)	C11—C12—H12A	109.6
C7—C8—C2	118.97 (13)	O13—C12—H12B	109.6
C7—C8—H8	120.5	C11—C12—H12B	109.6
C2—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.37 (11)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.50 (13)	C3—C5—C6—C7	−0.1 (2)
C4ⁱ—S1—C2—C3	−0.58 (10)	C5—C6—C7—C8	0.3 (2)
C8—C2—C3—C5	1.3 (2)	C5—C6—C7—C9	−177.80 (13)
S1—C2—C3—C5	−178.64 (10)	C6—C7—C8—C2	0.3 (2)
C8—C2—C3—C4	−179.54 (12)	C9—C7—C8—C2	178.39 (12)
S1—C2—C3—C4	0.54 (14)	C3—C2—C8—C7	−1.1 (2)
C5—C3—C4—C4ⁱ	178.87 (15)	S1—C2—C8—C7	178.80 (10)
C2—C3—C4—C4ⁱ	−0.2 (2)	C8—C7—C9—C10	−79.38 (17)
C5—C3—C4—S1ⁱ	−1.5 (2)	C6—C7—C9—C10	98.67 (16)
C2—C3—C4—S1ⁱ	179.49 (11)	C7—C9—C10—C11	−176.06 (13)
C2—C3—C5—C6	−0.7 (2)	C9—C10—C11—C12	−175.13 (13)
C4—C3—C5—C6	−179.63 (14)	C10—C11—C12—O13	179.88 (12)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.82	2.02	2.7977 (10)	160
C6—H6···S1ⁱⁱⁱ	0.95	3.31	4.1072 (14)	142
C9—H9A···S1ⁱⁱⁱ	0.99	3.44	4.0793 (16)	124
C10—H10A···S1ⁱⁱⁱ	0.99	3.32	3.9365 (17)	122
C10—H10A···S1^iv	0.99	3.14	3.8421 (16)	129
C11—H11B···S1ⁱⁱⁱ	0.99	3.41	4.1051 (16)	129
C12—H12A···S1^iv	0.99	3.06	3.8146 (16)	134

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A160) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.366 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.496 (3) Å	Cell parameters from 7083 reflections
b = 5.070 (1) Å	θ = 2.4–25.5°
c = 14.303 (1) Å	µ = 0.29 mm⁻¹
β = 107.255 (14)°	T = 160 K
V = 934.6 (3) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.021
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8282 measured reflections	h = −19→19
2741 independent reflections	k = −6→7
2463 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0604P)² + 0.3814P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
2741 reflections	Δρ_max = 0.83 e Å⁻³
121 parameters	Δρ_min = −0.43 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.006 (3)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64677 (2)	0.32349 (7)	0.53772 (2)	0.02997 (13)
C2	0.64870 (10)	0.5553 (3)	0.62887 (9)	0.0263 (3)
C3	0.55388 (10)	0.6914 (3)	0.61197 (9)	0.0259 (3)
C4	0.48095 (10)	0.5971 (3)	0.52328 (9)	0.0260 (3)
C5	0.54481 (11)	0.8869 (3)	0.67770 (10)	0.0305 (3)
H5	0.481858	0.982238	0.667242	0.037*
C6	0.62899 (11)	0.9394 (3)	0.75829 (10)	0.0309 (3)
H6	0.622901	1.072455	0.803035	0.037*
C7	0.72326 (11)	0.8021 (3)	0.77607 (9)	0.0286 (3)
C8	0.73296 (11)	0.6081 (3)	0.71098 (10)	0.0293 (3)
H8	0.795958	0.512629	0.722060	0.035*
C9	0.81147 (11)	0.8606 (3)	0.86704 (10)	0.0308 (3)
H9A	0.802077	1.039503	0.890843	0.037*
H9B	0.877615	0.859090	0.850363	0.037*
C10	0.81792 (12)	0.6620 (3)	0.94833 (10)	0.0326 (3)
H10A	0.749901	0.654449	0.961342	0.039*
H10B	0.831959	0.485176	0.925755	0.039*
C11	0.90174 (11)	0.7268 (3)	1.04363 (9)	0.0297 (3)
H11A	0.969086	0.748944	1.030131	0.036*
H11B	0.884553	0.895686	1.069925	0.036*
C12	0.91156 (12)	0.5135 (3)	1.11897 (10)	0.0322 (3)
H12A	0.844544	0.491627	1.133139	0.039*
H12B	0.928919	0.344250	1.093084	0.039*
O13	0.99050 (9)	0.5796 (2)	1.20678 (7)	0.0355 (3)
H13	0.9989 (13)	0.459 (4)	1.2443 (13)	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02736 (18)	0.0348 (2)	0.02615 (18)	0.00399 (12)	0.00544 (12)	−0.00640 (12)
C2	0.0288 (6)	0.0282 (6)	0.0224 (5)	−0.0007 (5)	0.0083 (4)	−0.0013 (4)
C3	0.0288 (6)	0.0275 (6)	0.0222 (5)	−0.0015 (4)	0.0088 (4)	−0.0013 (4)
C4	0.0264 (5)	0.0290 (6)	0.0227 (5)	0.0003 (5)	0.0077 (4)	−0.0010 (5)
C5	0.0322 (6)	0.0326 (7)	0.0266 (6)	0.0009 (5)	0.0087 (5)	−0.0055 (5)
C6	0.0366 (7)	0.0313 (7)	0.0245 (6)	−0.0033 (5)	0.0085 (5)	−0.0050 (5)
C7	0.0324 (6)	0.0307 (7)	0.0213 (5)	−0.0064 (5)	0.0058 (5)	0.0003 (5)
C8	0.0285 (6)	0.0329 (7)	0.0252 (6)	−0.0013 (5)	0.0060 (5)	−0.0013 (5)
C9	0.0343 (7)	0.0308 (7)	0.0238 (6)	−0.0078 (5)	0.0031 (5)	−0.0010 (5)
C10	0.0407 (7)	0.0267 (7)	0.0245 (6)	−0.0072 (5)	0.0008 (5)	−0.0010 (5)
C11	0.0364 (6)	0.0255 (6)	0.0233 (6)	−0.0041 (5)	0.0030 (5)	−0.0018 (5)
C12	0.0402 (7)	0.0272 (6)	0.0244 (6)	−0.0030 (5)	0.0021 (5)	−0.0009 (5)
O13	0.0425 (6)	0.0322 (6)	0.0247 (5)	−0.0017 (4)	−0.0012 (4)	−0.0001 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7327 (14)	C9—C10	1.521 (2)
S1—C2	1.7495 (13)	C9—H9A	0.9900
C2—C8	1.3971 (18)	C9—H9B	0.9900
C2—C3	1.4102 (18)	C10—C11	1.5267 (19)
C3—C5	1.3964 (18)	C10—H10A	0.9900
C3—C4	1.4372 (17)	C10—H10B	0.9900
C4—C4ⁱ	1.371 (3)	C11—C12	1.5044 (19)
C5—C6	1.3833 (18)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.406 (2)	C12—O13	1.4251 (16)
C6—H6	0.9500	C12—H12A	0.9900
C7—C8	1.3869 (19)	C12—H12B	0.9900
C7—C9	1.5097 (18)	O13—H13	0.80 (2)
C8—H8	0.9500

C4ⁱ—S1—C2	90.68 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.41 (12)	C7—C9—H9B	109.1
C8—C2—S1	125.72 (11)	C10—C9—H9B	109.1
C3—C2—S1	112.87 (10)	H9A—C9—H9B	107.9
C5—C3—C2	119.23 (12)	C11—C10—C9	113.53 (12)
C5—C3—C4	131.02 (12)	C11—C10—H10A	108.9
C2—C3—C4	109.74 (11)	C9—C10—H10A	108.9
C4ⁱ—C4—C3	114.21 (14)	C11—C10—H10B	108.9
C4ⁱ—C4—S1ⁱ	112.50 (13)	C9—C10—H10B	108.9
C3—C4—S1ⁱ	133.30 (10)	H10A—C10—H10B	107.7
C6—C5—C3	118.90 (13)	C12—C11—C10	111.67 (12)
C6—C5—H5	120.5	C12—C11—H11A	109.3
C3—C5—H5	120.5	C10—C11—H11A	109.3
C5—C6—C7	122.07 (13)	C12—C11—H11B	109.3
C5—C6—H6	119.0	C10—C11—H11B	109.3
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.36 (12)	O13—C12—C11	110.26 (12)
C8—C7—C9	120.70 (13)	O13—C12—H12A	109.6
C6—C7—C9	119.91 (13)	C11—C12—H12A	109.6
C7—C8—C2	119.01 (13)	O13—C12—H12B	109.6
C7—C8—H8	120.5	C11—C12—H12B	109.6
C2—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.35 (11)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.49 (13)	C3—C5—C6—C7	0.0 (2)
C4ⁱ—S1—C2—C3	−0.60 (11)	C5—C6—C7—C8	0.2 (2)
C8—C2—C3—C5	1.3 (2)	C5—C6—C7—C9	−177.86 (13)
S1—C2—C3—C5	−178.58 (11)	C6—C7—C8—C2	0.4 (2)
C8—C2—C3—C4	−179.57 (12)	C9—C7—C8—C2	178.44 (12)
S1—C2—C3—C4	0.51 (14)	C3—C2—C8—C7	−1.2 (2)
C5—C3—C4—C4ⁱ	178.84 (15)	S1—C2—C8—C7	178.74 (11)
C2—C3—C4—C4ⁱ	−0.1 (2)	C8—C7—C9—C10	−79.43 (17)
C5—C3—C4—S1ⁱ	−1.6 (2)	C6—C7—C9—C10	98.61 (16)
C2—C3—C4—S1ⁱ	179.45 (11)	C7—C9—C10—C11	−176.05 (13)
C2—C3—C5—C6	−0.7 (2)	C9—C10—C11—C12	−175.07 (13)
C4—C3—C5—C6	−179.59 (14)	C10—C11—C12—O13	179.84 (12)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.80	2.04	2.7986 (10)	159
C6—H6···S1ⁱⁱⁱ	0.95	3.32	4.1118 (14)	142
C9—H9A···S1ⁱⁱⁱ	0.99	3.45	4.0847 (17)	124
C10—H10A···S1ⁱⁱⁱ	0.99	3.32	3.9404 (18)	122
C10—H10A···S1^iv	0.99	3.15	3.8446 (16)	129
C11—H11B···S1ⁱⁱⁱ	0.99	3.41	4.1078 (17)	129
C12—H12A···S1^iv	0.99	3.06	3.8180 (17)	134

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A170) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.364 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.508 (3) Å	Cell parameters from 6920 reflections
b = 5.073 (1) Å	θ = 2.4–24.3°
c = 14.312 (1) Å	µ = 0.29 mm⁻¹
β = 107.316 (13)°	T = 170 K
V = 936.3 (3) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.023
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8289 measured reflections	h = −19→19
2751 independent reflections	k = −6→7
2471 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0605P)² + 0.3871P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
2751 reflections	Δρ_max = 0.80 e Å⁻³
121 parameters	Δρ_min = −0.41 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.005 (3)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64665 (3)	0.32349 (8)	0.53781 (2)	0.03141 (13)
C2	0.64861 (10)	0.5552 (3)	0.62891 (9)	0.0274 (3)
C3	0.55389 (10)	0.6911 (3)	0.61197 (9)	0.0270 (3)
C4	0.48100 (10)	0.5970 (3)	0.52330 (9)	0.0273 (3)
C5	0.54484 (11)	0.8864 (3)	0.67777 (10)	0.0319 (3)
H5	0.481888	0.981428	0.667326	0.038*
C6	0.62888 (11)	0.9391 (3)	0.75830 (10)	0.0325 (3)
H6	0.622802	1.072171	0.802957	0.039*
C7	0.72317 (11)	0.8017 (3)	0.77618 (9)	0.0299 (3)
C8	0.73277 (11)	0.6080 (3)	0.71100 (10)	0.0308 (3)
H8	0.795731	0.512520	0.722082	0.037*
C9	0.81135 (12)	0.8603 (3)	0.86708 (10)	0.0324 (3)
H9A	0.801991	1.039086	0.890831	0.039*
H9B	0.877422	0.858637	0.850426	0.039*
C10	0.81785 (13)	0.6618 (3)	0.94840 (10)	0.0342 (3)
H10A	0.749905	0.654434	0.961403	0.041*
H10B	0.831824	0.485071	0.925866	0.041*
C11	0.90164 (12)	0.7266 (3)	1.04360 (9)	0.0311 (3)
H11A	0.968926	0.748464	1.030113	0.037*
H11B	0.884548	0.895476	1.069830	0.037*
C12	0.91148 (12)	0.5136 (3)	1.11901 (10)	0.0336 (3)
H12A	0.844514	0.491900	1.133126	0.040*
H12B	0.928781	0.344342	1.093189	0.040*
O13	0.99036 (9)	0.5796 (2)	1.20677 (7)	0.0373 (3)
H13	0.9998 (13)	0.456 (4)	1.2447 (13)	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02865 (18)	0.0365 (2)	0.02729 (18)	0.00422 (12)	0.00559 (13)	−0.00672 (12)
C2	0.0298 (6)	0.0292 (6)	0.0233 (5)	−0.0008 (5)	0.0083 (4)	−0.0012 (5)
C3	0.0295 (6)	0.0290 (6)	0.0231 (5)	−0.0017 (5)	0.0089 (4)	−0.0013 (4)
C4	0.0278 (5)	0.0306 (6)	0.0239 (5)	0.0003 (5)	0.0081 (4)	−0.0012 (5)
C5	0.0339 (6)	0.0342 (7)	0.0275 (6)	0.0007 (5)	0.0090 (5)	−0.0054 (5)
C6	0.0388 (7)	0.0330 (7)	0.0255 (6)	−0.0036 (5)	0.0092 (5)	−0.0054 (5)
C7	0.0338 (6)	0.0324 (7)	0.0218 (5)	−0.0068 (5)	0.0057 (5)	0.0002 (5)
C8	0.0301 (6)	0.0339 (7)	0.0268 (6)	−0.0017 (5)	0.0061 (5)	−0.0018 (5)
C9	0.0362 (7)	0.0325 (7)	0.0245 (6)	−0.0083 (5)	0.0029 (5)	−0.0010 (5)
C10	0.0430 (8)	0.0280 (7)	0.0255 (6)	−0.0077 (5)	0.0007 (5)	−0.0009 (5)
C11	0.0381 (7)	0.0268 (6)	0.0243 (6)	−0.0046 (5)	0.0029 (5)	−0.0021 (5)
C12	0.0422 (7)	0.0280 (7)	0.0254 (6)	−0.0031 (5)	0.0020 (5)	−0.0009 (5)
O13	0.0445 (6)	0.0337 (6)	0.0258 (5)	−0.0016 (4)	−0.0017 (4)	0.0001 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7330 (14)	C9—C10	1.521 (2)
S1—C2	1.7499 (13)	C9—H9A	0.9900
C2—C8	1.3962 (18)	C9—H9B	0.9900
C2—C3	1.4095 (19)	C10—C11	1.5255 (19)
C3—C5	1.3968 (18)	C10—H10A	0.9900
C3—C4	1.4368 (17)	C10—H10B	0.9900
C4—C4ⁱ	1.371 (3)	C11—C12	1.505 (2)
C5—C6	1.3819 (19)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.407 (2)	C12—O13	1.4242 (16)
C6—H6	0.9500	C12—H12A	0.9900
C7—C8	1.388 (2)	C12—H12B	0.9900
C7—C9	1.5090 (18)	O13—H13	0.82 (2)
C8—H8	0.9500

C4ⁱ—S1—C2	90.67 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.41 (12)	C7—C9—H9B	109.1
C8—C2—S1	125.71 (11)	C10—C9—H9B	109.1
C3—C2—S1	112.88 (10)	H9A—C9—H9B	107.9
C5—C3—C2	119.21 (12)	C11—C10—C9	113.54 (12)
C5—C3—C4	131.05 (13)	C11—C10—H10A	108.9
C2—C3—C4	109.73 (11)	C9—C10—H10A	108.9
C4ⁱ—C4—C3	114.26 (15)	C11—C10—H10B	108.9
C4ⁱ—C4—S1ⁱ	112.45 (13)	C9—C10—H10B	108.9
C3—C4—S1ⁱ	133.29 (10)	H10A—C10—H10B	107.7
C6—C5—C3	118.98 (13)	C12—C11—C10	111.70 (12)
C6—C5—H5	120.5	C12—C11—H11A	109.3
C3—C5—H5	120.5	C10—C11—H11A	109.3
C5—C6—C7	122.03 (13)	C12—C11—H11B	109.3
C5—C6—H6	119.0	C10—C11—H11B	109.3
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.30 (12)	O13—C12—C11	110.31 (12)
C8—C7—C9	120.75 (13)	O13—C12—H12A	109.6
C6—C7—C9	119.93 (13)	C11—C12—H12A	109.6
C7—C8—C2	119.07 (13)	O13—C12—H12B	109.6
C7—C8—H8	120.5	C11—C12—H12B	109.6
C2—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.36 (12)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.49 (13)	C3—C5—C6—C7	−0.2 (2)
C4ⁱ—S1—C2—C3	−0.55 (11)	C5—C6—C7—C8	0.3 (2)
C8—C2—C3—C5	1.3 (2)	C5—C6—C7—C9	−177.86 (13)
S1—C2—C3—C5	−178.67 (11)	C6—C7—C8—C2	0.3 (2)
C8—C2—C3—C4	−179.55 (12)	C9—C7—C8—C2	178.50 (13)
S1—C2—C3—C4	0.49 (15)	C3—C2—C8—C7	−1.2 (2)
C5—C3—C4—C4ⁱ	178.88 (16)	S1—C2—C8—C7	178.81 (11)
C2—C3—C4—C4ⁱ	−0.1 (2)	C8—C7—C9—C10	−79.53 (18)
C5—C3—C4—S1ⁱ	−1.5 (2)	C6—C7—C9—C10	98.62 (17)
C2—C3—C4—S1ⁱ	179.52 (11)	C7—C9—C10—C11	−176.07 (13)
C2—C3—C5—C6	−0.6 (2)	C9—C10—C11—C12	−175.10 (13)
C4—C3—C5—C6	−179.57 (14)	C10—C11—C12—O13	179.87 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.82	2.02	2.8002 (10)	160
C6—H6···S1ⁱⁱⁱ	0.95	3.32	4.1158 (14)	142
C9—H9A···S1ⁱⁱⁱ	0.99	3.46	4.0902 (17)	124
C10—H10A···S1ⁱⁱⁱ	0.99	3.33	3.9450 (18)	122
C10—H10A···S1^iv	0.99	3.15	3.8482 (16)	129
C11—H11B···S1ⁱⁱⁱ	0.99	3.42	4.1123 (17)	129
C12—H12A···S1^iv	0.99	3.06	3.8207 (17)	134

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A180) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.361 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.521 (3) Å	Cell parameters from 6914 reflections
b = 5.076 (1) Å	θ = 2.4–24.7°
c = 14.322 (1) Å	µ = 0.29 mm⁻¹
β = 107.384 (14)°	T = 180 K
V = 938.1 (3) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.022
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8298 measured reflections	h = −19→19
2758 independent reflections	k = −6→7
2465 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0603P)² + 0.4239P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2758 reflections	Δρ_max = 0.81 e Å⁻³
121 parameters	Δρ_min = −0.45 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.006 (3)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64652 (3)	0.32353 (8)	0.53791 (2)	0.03306 (13)
C2	0.64847 (11)	0.5551 (3)	0.62900 (9)	0.0288 (3)
C3	0.55387 (11)	0.6910 (3)	0.61195 (10)	0.0283 (3)
C4	0.48101 (10)	0.5969 (3)	0.52329 (9)	0.0285 (3)
C5	0.54489 (12)	0.8858 (3)	0.67780 (10)	0.0333 (3)
H5	0.481935	0.980543	0.667410	0.040*
C6	0.62893 (12)	0.9386 (3)	0.75832 (10)	0.0339 (3)
H6	0.622884	1.071749	0.802915	0.041*
C7	0.72307 (11)	0.8014 (3)	0.77625 (10)	0.0312 (3)
C8	0.73270 (11)	0.6078 (3)	0.71110 (10)	0.0321 (3)
H8	0.795643	0.512570	0.722182	0.038*
C9	0.81118 (12)	0.8599 (3)	0.86713 (10)	0.0342 (3)
H9A	0.801884	1.038682	0.890817	0.041*
H9B	0.877207	0.858089	0.850549	0.041*
C10	0.81772 (13)	0.6620 (3)	0.94844 (11)	0.0358 (3)
H10A	0.749825	0.654868	0.961382	0.043*
H10B	0.831566	0.485256	0.925930	0.043*
C11	0.90150 (12)	0.7263 (3)	1.04369 (10)	0.0326 (3)
H11A	0.968745	0.747966	1.030275	0.039*
H11B	0.884513	0.895114	1.069920	0.039*
C12	0.91131 (12)	0.5136 (3)	1.11905 (10)	0.0351 (3)
H12A	0.844415	0.491987	1.133145	0.042*
H12B	0.928558	0.344296	1.093285	0.042*
O13	0.99025 (9)	0.5798 (2)	1.20678 (8)	0.0393 (3)
H13	0.9996 (14)	0.458 (4)	1.2441 (14)	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02995 (19)	0.0385 (2)	0.02873 (19)	0.00444 (13)	0.00576 (13)	−0.00705 (13)
C2	0.0315 (6)	0.0309 (7)	0.0245 (5)	−0.0008 (5)	0.0090 (5)	−0.0013 (5)
C3	0.0308 (6)	0.0302 (7)	0.0244 (6)	−0.0017 (5)	0.0091 (5)	−0.0014 (5)
C4	0.0291 (6)	0.0317 (7)	0.0246 (5)	−0.0001 (5)	0.0081 (5)	−0.0013 (5)
C5	0.0347 (7)	0.0358 (7)	0.0291 (6)	0.0006 (5)	0.0089 (5)	−0.0058 (5)
C6	0.0399 (7)	0.0345 (7)	0.0270 (6)	−0.0036 (6)	0.0092 (5)	−0.0057 (5)
C7	0.0353 (7)	0.0330 (7)	0.0235 (6)	−0.0071 (5)	0.0060 (5)	0.0003 (5)
C8	0.0312 (6)	0.0357 (7)	0.0277 (6)	−0.0013 (5)	0.0064 (5)	−0.0013 (5)
C9	0.0380 (7)	0.0342 (7)	0.0259 (6)	−0.0086 (6)	0.0027 (5)	−0.0009 (5)
C10	0.0448 (8)	0.0292 (7)	0.0267 (6)	−0.0078 (6)	0.0006 (5)	−0.0007 (5)
C11	0.0397 (7)	0.0275 (7)	0.0259 (6)	−0.0053 (5)	0.0027 (5)	−0.0021 (5)
C12	0.0437 (8)	0.0293 (7)	0.0267 (6)	−0.0032 (6)	0.0018 (5)	−0.0010 (5)
O13	0.0466 (6)	0.0358 (6)	0.0269 (5)	−0.0019 (5)	−0.0020 (4)	0.0003 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7325 (14)	C9—C10	1.520 (2)
S1—C2	1.7505 (14)	C9—H9A	0.9900
C2—C8	1.3968 (19)	C9—H9B	0.9900
C2—C3	1.4088 (19)	C10—C11	1.5255 (19)
C3—C5	1.3965 (19)	C10—H10A	0.9900
C3—C4	1.4364 (18)	C10—H10B	0.9900
C4—C4ⁱ	1.372 (3)	C11—C12	1.504 (2)
C5—C6	1.3819 (19)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.406 (2)	C12—O13	1.4246 (17)
C6—H6	0.9500	C12—H12A	0.9900
C7—C8	1.388 (2)	C12—H12B	0.9900
C7—C9	1.5084 (19)	O13—H13	0.80 (3)
C8—H8	0.9500

C4ⁱ—S1—C2	90.67 (7)	C10—C9—H9A	109.1
C8—C2—C3	121.46 (13)	C7—C9—H9B	109.1
C8—C2—S1	125.66 (11)	C10—C9—H9B	109.1
C3—C2—S1	112.88 (10)	H9A—C9—H9B	107.9
C5—C3—C2	119.15 (12)	C11—C10—C9	113.67 (12)
C5—C3—C4	131.09 (13)	C11—C10—H10A	108.8
C2—C3—C4	109.75 (12)	C9—C10—H10A	108.8
C4ⁱ—C4—C3	114.25 (15)	C11—C10—H10B	108.8
C4ⁱ—C4—S1ⁱ	112.44 (14)	C9—C10—H10B	108.8
C3—C4—S1ⁱ	133.30 (11)	H10A—C10—H10B	107.7
C6—C5—C3	119.03 (14)	C12—C11—C10	111.78 (12)
C6—C5—H5	120.5	C12—C11—H11A	109.3
C3—C5—H5	120.5	C10—C11—H11A	109.3
C5—C6—C7	122.02 (13)	C12—C11—H11B	109.3
C5—C6—H6	119.0	C10—C11—H11B	109.3
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.33 (13)	O13—C12—C11	110.23 (12)
C8—C7—C9	120.72 (14)	O13—C12—H12A	109.6
C6—C7—C9	119.93 (13)	C11—C12—H12A	109.6
C7—C8—C2	119.00 (14)	O13—C12—H12B	109.6
C7—C8—H8	120.5	C11—C12—H12B	109.6
C2—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.41 (12)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.57 (14)	C3—C5—C6—C7	−0.3 (2)
C4ⁱ—S1—C2—C3	−0.58 (11)	C5—C6—C7—C8	0.4 (2)
C8—C2—C3—C5	1.1 (2)	C5—C6—C7—C9	−177.80 (14)
S1—C2—C3—C5	−178.74 (11)	C6—C7—C8—C2	0.3 (2)
C8—C2—C3—C4	−179.59 (13)	C9—C7—C8—C2	178.45 (13)
S1—C2—C3—C4	0.55 (15)	C3—C2—C8—C7	−1.0 (2)
C5—C3—C4—C4ⁱ	178.97 (16)	S1—C2—C8—C7	178.81 (11)
C2—C3—C4—C4ⁱ	−0.2 (2)	C8—C7—C9—C10	−79.61 (19)
C5—C3—C4—S1ⁱ	−1.3 (3)	C6—C7—C9—C10	98.56 (17)
C2—C3—C4—S1ⁱ	179.51 (12)	C7—C9—C10—C11	−176.11 (14)
C2—C3—C5—C6	−0.4 (2)	C9—C10—C11—C12	−175.07 (14)
C4—C3—C5—C6	−179.55 (14)	C10—C11—C12—O13	179.88 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.80	2.04	2.8015 (10)	160
C6—H6···S1ⁱⁱⁱ	0.95	3.33	4.1206 (14)	142
C9—H9A···S1ⁱⁱⁱ	0.99	3.46	4.0958 (18)	124
C10—H10A···S1ⁱⁱⁱ	0.99	3.33	3.9486 (19)	122
C10—H10A···S1^iv	0.99	3.16	3.8532 (17)	129
C11—H11B···S1ⁱⁱⁱ	0.99	3.42	4.1164 (18)	129
C12—H12A···S1^iv	0.99	3.07	3.8224 (18)	134

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A190) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.535 (3) Å	Cell parameters from 7082 reflections
b = 5.078 (1) Å	θ = 2.3–24.6°
c = 14.332 (1) Å	µ = 0.29 mm⁻¹
β = 107.455 (15)°	T = 190 K
V = 939.7 (3) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.022
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8316 measured reflections	h = −19→19
2767 independent reflections	k = −6→7
2452 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.0645P)² + 0.3676P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
2767 reflections	Δρ_max = 0.80 e Å⁻³
121 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.007 (3)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64639 (3)	0.32366 (8)	0.53801 (3)	0.03487 (14)
C2	0.64839 (11)	0.5549 (3)	0.62917 (10)	0.0303 (3)
C3	0.55377 (11)	0.6905 (3)	0.61193 (10)	0.0298 (3)
C4	0.48105 (11)	0.5970 (3)	0.52324 (10)	0.0300 (3)
C5	0.54489 (12)	0.8852 (3)	0.67774 (11)	0.0352 (3)
H5	0.481966	0.979859	0.667304	0.042*
C6	0.62890 (12)	0.9383 (3)	0.75827 (10)	0.0360 (3)
H6	0.622866	1.071633	0.802744	0.043*
C7	0.72297 (12)	0.8011 (3)	0.77638 (10)	0.0329 (3)
C8	0.73256 (11)	0.6077 (3)	0.71111 (11)	0.0340 (3)
H8	0.795504	0.512824	0.722110	0.041*
C9	0.81105 (13)	0.8594 (3)	0.86716 (11)	0.0360 (3)
H9A	0.801878	1.038257	0.890750	0.043*
H9B	0.876980	0.857233	0.850580	0.043*
C10	0.81767 (14)	0.6618 (3)	0.94866 (11)	0.0377 (3)
H10A	0.749865	0.654952	0.961623	0.045*
H10B	0.831417	0.484939	0.926274	0.045*
C11	0.90139 (12)	0.7262 (3)	1.04369 (10)	0.0344 (3)
H11A	0.968558	0.747532	1.030265	0.041*
H11B	0.884521	0.895187	1.069812	0.041*
C12	0.91118 (13)	0.5138 (3)	1.11914 (11)	0.0371 (3)
H12A	0.844348	0.492610	1.133219	0.045*
H12B	0.928284	0.344412	1.093455	0.045*
O13	0.99007 (10)	0.5798 (2)	1.20674 (8)	0.0415 (3)
H13	0.9994 (14)	0.457 (4)	1.2444 (14)	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0315 (2)	0.0406 (2)	0.0304 (2)	0.00461 (13)	0.00597 (14)	−0.00738 (13)
C2	0.0327 (6)	0.0327 (7)	0.0257 (6)	−0.0008 (5)	0.0091 (5)	−0.0013 (5)
C3	0.0323 (6)	0.0321 (7)	0.0256 (6)	−0.0021 (5)	0.0095 (5)	−0.0013 (5)
C4	0.0306 (6)	0.0334 (7)	0.0260 (6)	0.0004 (5)	0.0084 (5)	−0.0016 (5)
C5	0.0375 (7)	0.0377 (7)	0.0302 (6)	0.0005 (6)	0.0097 (5)	−0.0060 (6)
C6	0.0422 (8)	0.0367 (8)	0.0283 (6)	−0.0038 (6)	0.0095 (6)	−0.0058 (5)
C7	0.0370 (7)	0.0347 (7)	0.0249 (6)	−0.0069 (5)	0.0064 (5)	0.0003 (5)
C8	0.0328 (6)	0.0379 (7)	0.0294 (6)	−0.0015 (5)	0.0066 (5)	−0.0016 (5)
C9	0.0402 (7)	0.0358 (7)	0.0273 (6)	−0.0089 (6)	0.0032 (5)	−0.0013 (5)
C10	0.0469 (8)	0.0310 (7)	0.0279 (6)	−0.0080 (6)	0.0002 (6)	−0.0006 (5)
C11	0.0419 (7)	0.0293 (7)	0.0270 (6)	−0.0052 (6)	0.0026 (5)	−0.0023 (5)
C12	0.0461 (8)	0.0305 (7)	0.0285 (6)	−0.0035 (6)	0.0017 (5)	−0.0010 (5)
O13	0.0492 (6)	0.0374 (6)	0.0286 (5)	−0.0017 (5)	−0.0021 (4)	0.0004 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7321 (15)	C9—C10	1.522 (2)
S1—C2	1.7509 (14)	C9—H9A	0.9900
C2—C8	1.3951 (19)	C9—H9B	0.9900
C2—C3	1.409 (2)	C10—C11	1.523 (2)
C3—C5	1.3961 (19)	C10—H10A	0.9900
C3—C4	1.4350 (18)	C10—H10B	0.9900
C4—C4ⁱ	1.372 (3)	C11—C12	1.505 (2)
C5—C6	1.382 (2)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.406 (2)	C12—O13	1.4228 (17)
C6—H6	0.9500	C12—H12A	0.9900
C7—C8	1.389 (2)	C12—H12B	0.9900
C7—C9	1.507 (2)	O13—H13	0.81 (3)
C8—H8	0.9500

C4ⁱ—S1—C2	90.71 (7)	C10—C9—H9A	109.1
C8—C2—C3	121.56 (13)	C7—C9—H9B	109.1
C8—C2—S1	125.67 (11)	C10—C9—H9B	109.1
C3—C2—S1	112.77 (10)	H9A—C9—H9B	107.8
C5—C3—C2	119.04 (13)	C11—C10—C9	113.67 (12)
C5—C3—C4	131.11 (13)	C11—C10—H10A	108.8
C2—C3—C4	109.84 (12)	C9—C10—H10A	108.8
C4ⁱ—C4—C3	114.25 (16)	C11—C10—H10B	108.8
C4ⁱ—C4—S1ⁱ	112.42 (14)	C9—C10—H10B	108.8
C3—C4—S1ⁱ	133.33 (11)	H10A—C10—H10B	107.7
C6—C5—C3	119.11 (14)	C12—C11—C10	111.73 (12)
C6—C5—H5	120.4	C12—C11—H11A	109.3
C3—C5—H5	120.4	C10—C11—H11A	109.3
C5—C6—C7	122.02 (14)	C12—C11—H11B	109.3
C5—C6—H6	119.0	C10—C11—H11B	109.3
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.24 (13)	O13—C12—C11	110.27 (13)
C8—C7—C9	120.72 (14)	O13—C12—H12A	109.6
C6—C7—C9	120.02 (14)	C11—C12—H12A	109.6
C7—C8—C2	119.03 (14)	O13—C12—H12B	109.6
C7—C8—H8	120.5	C11—C12—H12B	109.6
C2—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.49 (12)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.68 (14)	C3—C5—C6—C7	−0.4 (2)
C4ⁱ—S1—C2—C3	−0.61 (11)	C5—C6—C7—C8	0.6 (2)
C8—C2—C3—C5	1.1 (2)	C5—C6—C7—C9	−177.76 (14)
S1—C2—C3—C5	−178.65 (11)	C6—C7—C8—C2	0.0 (2)
C8—C2—C3—C4	−179.81 (13)	C9—C7—C8—C2	178.39 (13)
S1—C2—C3—C4	0.48 (16)	C3—C2—C8—C7	−0.9 (2)
C5—C3—C4—C4ⁱ	178.96 (17)	S1—C2—C8—C7	178.82 (11)
C2—C3—C4—C4ⁱ	0.0 (2)	C8—C7—C9—C10	−79.83 (19)
C5—C3—C4—S1ⁱ	−1.6 (3)	C6—C7—C9—C10	98.52 (18)
C2—C3—C4—S1ⁱ	179.42 (12)	C7—C9—C10—C11	−176.09 (14)
C2—C3—C5—C6	−0.4 (2)	C9—C10—C11—C12	−175.08 (14)
C4—C3—C5—C6	−179.33 (15)	C10—C11—C12—O13	179.87 (14)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.81	2.03	2.8029 (10)	160
C6—H6···S1ⁱⁱⁱ	0.95	3.33	4.1257 (15)	142
C9—H9A···S1ⁱⁱⁱ	0.99	3.47	4.1021 (18)	124
C10—H10A···S1ⁱⁱⁱ	0.99	3.33	3.9523 (19)	123
C10—H10A···S1^iv	0.99	3.16	3.8563 (18)	129
C11—H11B···S1ⁱⁱⁱ	0.99	3.43	4.1201 (19)	129
C12—H12A···S1^iv	0.99	3.07	3.8253 (18)	134

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A200) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.357 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.550 (2) Å	Cell parameters from 7071 reflections
b = 5.078 (1) Å	θ = 2.4–24.3°
c = 14.344 (2) Å	µ = 0.29 mm⁻¹
β = 107.529 (17)°	T = 200 K
V = 941.1 (2) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.023
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8206 measured reflections	h = −19→19
2773 independent reflections	k = −6→7
2418 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0697P)² + 0.4379P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
2773 reflections	Δρ_max = 0.82 e Å⁻³
121 parameters	Δρ_min = −0.64 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.012 (4)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64631 (3)	0.32361 (9)	0.53812 (3)	0.03699 (15)
C2	0.64831 (12)	0.5547 (3)	0.62921 (11)	0.0323 (3)
C3	0.55386 (12)	0.6903 (3)	0.61199 (11)	0.0318 (3)
C4	0.48109 (12)	0.5967 (3)	0.52328 (11)	0.0317 (3)
C5	0.54478 (13)	0.8847 (4)	0.67768 (12)	0.0371 (3)
H5	0.481879	0.979281	0.667196	0.044*
C6	0.62884 (14)	0.9374 (4)	0.75828 (11)	0.0380 (4)
H6	0.622785	1.070326	0.802850	0.046*
C7	0.72288 (13)	0.8008 (3)	0.77638 (11)	0.0349 (3)
C8	0.73246 (13)	0.6072 (4)	0.71127 (11)	0.0359 (3)
H8	0.795306	0.511947	0.722405	0.043*
C9	0.81104 (14)	0.8590 (4)	0.86728 (12)	0.0384 (4)
H9A	0.801990	1.037969	0.890819	0.046*
H9B	0.876928	0.856458	0.850809	0.046*
C10	0.81746 (15)	0.6621 (3)	0.94849 (12)	0.0398 (4)
H10A	0.749676	0.655627	0.961305	0.048*
H10B	0.831073	0.485135	0.926135	0.048*
C11	0.90124 (14)	0.7262 (3)	1.04373 (11)	0.0366 (3)
H11A	0.968359	0.747626	1.030411	0.044*
H11B	0.884396	0.895081	1.069884	0.044*
C12	0.91109 (15)	0.5137 (3)	1.11908 (12)	0.0395 (4)
H12A	0.844317	0.492335	1.133071	0.047*
H12B	0.928251	0.344436	1.093430	0.047*
O13	0.98997 (11)	0.5800 (3)	1.20676 (9)	0.0441 (3)
H13	0.9985 (15)	0.458 (5)	1.2451 (16)	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0339 (2)	0.0427 (3)	0.0319 (2)	0.00472 (15)	0.00612 (15)	−0.00774 (15)
C2	0.0351 (7)	0.0351 (8)	0.0268 (6)	−0.0008 (6)	0.0096 (5)	−0.0013 (5)
C3	0.0350 (7)	0.0342 (8)	0.0265 (6)	−0.0019 (6)	0.0096 (5)	−0.0014 (5)
C4	0.0332 (7)	0.0342 (8)	0.0272 (6)	0.0000 (6)	0.0084 (5)	−0.0018 (5)
C5	0.0398 (8)	0.0387 (8)	0.0320 (7)	0.0008 (6)	0.0097 (6)	−0.0061 (6)
C6	0.0446 (9)	0.0391 (9)	0.0293 (7)	−0.0044 (7)	0.0096 (6)	−0.0066 (6)
C7	0.0401 (8)	0.0367 (8)	0.0254 (6)	−0.0076 (6)	0.0063 (6)	0.0003 (5)
C8	0.0357 (7)	0.0398 (8)	0.0300 (7)	−0.0021 (6)	0.0066 (6)	−0.0019 (6)
C9	0.0437 (8)	0.0381 (8)	0.0285 (7)	−0.0096 (7)	0.0036 (6)	−0.0010 (6)
C10	0.0495 (9)	0.0330 (8)	0.0297 (7)	−0.0086 (7)	0.0008 (6)	−0.0007 (6)
C11	0.0448 (8)	0.0308 (7)	0.0283 (7)	−0.0054 (6)	0.0022 (6)	−0.0021 (6)
C12	0.0497 (9)	0.0324 (8)	0.0294 (7)	−0.0036 (7)	0.0014 (6)	−0.0007 (6)
O13	0.0526 (7)	0.0397 (7)	0.0301 (6)	−0.0023 (6)	−0.0023 (5)	0.0004 (5)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7330 (16)	C9—C10	1.517 (2)
S1—C2	1.7503 (16)	C9—H9A	0.9900
C2—C8	1.396 (2)	C9—H9B	0.9900
C2—C3	1.408 (2)	C10—C11	1.525 (2)
C3—C5	1.395 (2)	C10—H10A	0.9900
C3—C4	1.436 (2)	C10—H10B	0.9900
C4—C4ⁱ	1.371 (3)	C11—C12	1.504 (2)
C5—C6	1.383 (2)	C11—H11A	0.9900
C5—H5	0.9500	C11—H11B	0.9900
C6—C7	1.405 (3)	C12—O13	1.4239 (19)
C6—H6	0.9500	C12—H12A	0.9900
C7—C8	1.389 (2)	C12—H12B	0.9900
C7—C9	1.509 (2)	O13—H13	0.81 (3)
C8—H8	0.9500

C4ⁱ—S1—C2	90.68 (7)	C10—C9—H9A	109.1
C8—C2—C3	121.54 (15)	C7—C9—H9B	109.1
C8—C2—S1	125.63 (13)	C10—C9—H9B	109.1
C3—C2—S1	112.83 (11)	H9A—C9—H9B	107.8
C5—C3—C2	119.20 (14)	C11—C10—C9	113.71 (14)
C5—C3—C4	130.99 (15)	C11—C10—H10A	108.8
C2—C3—C4	109.81 (14)	C9—C10—H10A	108.8
C4ⁱ—C4—C3	114.28 (18)	C11—C10—H10B	108.8
C4ⁱ—C4—S1ⁱ	112.39 (15)	C9—C10—H10B	108.8
C3—C4—S1ⁱ	133.33 (12)	H10A—C10—H10B	107.7
C6—C5—C3	118.92 (16)	C12—C11—C10	111.81 (14)
C6—C5—H5	120.5	C12—C11—H11A	109.3
C3—C5—H5	120.5	C10—C11—H11A	109.3
C5—C6—C7	122.12 (15)	C12—C11—H11B	109.3
C5—C6—H6	118.9	C10—C11—H11B	109.3
C7—C6—H6	118.9	H11A—C11—H11B	107.9
C8—C7—C6	119.26 (15)	O13—C12—C11	110.22 (14)
C8—C7—C9	120.65 (16)	O13—C12—H12A	109.6
C6—C7—C9	120.07 (15)	C11—C12—H12A	109.6
C7—C8—C2	118.95 (16)	O13—C12—H12B	109.6
C7—C8—H8	120.5	C11—C12—H12B	109.6
C2—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.44 (14)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.66 (16)	C3—C5—C6—C7	−0.3 (3)
C4ⁱ—S1—C2—C3	−0.57 (13)	C5—C6—C7—C8	0.3 (3)
C8—C2—C3—C5	1.1 (2)	C5—C6—C7—C9	−177.81 (16)
S1—C2—C3—C5	−178.72 (13)	C6—C7—C8—C2	0.3 (2)
C8—C2—C3—C4	−179.69 (15)	C9—C7—C8—C2	178.46 (15)
S1—C2—C3—C4	0.53 (17)	C3—C2—C8—C7	−1.0 (2)
C5—C3—C4—C4ⁱ	178.94 (18)	S1—C2—C8—C7	178.72 (13)
C2—C3—C4—C4ⁱ	−0.2 (2)	C8—C7—C9—C10	−79.8 (2)
C5—C3—C4—S1ⁱ	−1.4 (3)	C6—C7—C9—C10	98.3 (2)
C2—C3—C4—S1ⁱ	179.51 (13)	C7—C9—C10—C11	−176.08 (16)
C2—C3—C5—C6	−0.4 (2)	C9—C10—C11—C12	−174.94 (16)
C4—C3—C5—C6	−179.45 (16)	C10—C11—C12—O13	179.91 (16)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.81	2.03	2.8029 (10)	159
C6—H6···S1ⁱⁱⁱ	0.95	3.34	4.1314 (17)	143
C9—H9A···S1ⁱⁱⁱ	0.99	3.48	4.109 (2)	124
C10—H10A···S1ⁱⁱⁱ	0.99	3.33	3.956 (2)	123
C10—H10A···S1^iv	0.99	3.17	3.8614 (19)	129
C11—H11B···S1ⁱⁱⁱ	0.99	3.43	4.123 (2)	129
C12—H12A···S1^iv	0.99	3.07	3.8270 (19)	134

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A210) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.355 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.569 (2) Å	Cell parameters from 7094 reflections
b = 5.078 (1) Å	θ = 2.4–24.1°
c = 14.355 (2) Å	µ = 0.29 mm⁻¹
β = 107.612 (18)°	T = 210 K
V = 942.7 (2) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.026
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8423 measured reflections	h = −19→19
2785 independent reflections	k = −6→7
2507 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0657P)² + 0.3341P] where P = (F_o² + 2F_c²)/3
2785 reflections	(Δ/σ)_max = 0.001
120 parameters	Δρ_max = 0.65 e Å⁻³
0 restraints	Δρ_min = −0.54 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
S1	0.64615 (3)	0.32373 (8)	0.53817 (2)	0.03642 (13)
C2	0.64810 (10)	0.5545 (3)	0.62911 (9)	0.0313 (3)
C3	0.55382 (10)	0.6902 (3)	0.61197 (9)	0.0304 (3)
C4	0.48107 (10)	0.5967 (3)	0.52317 (9)	0.0309 (3)
C5	0.54488 (11)	0.8844 (3)	0.67770 (10)	0.0366 (3)
H5	0.482697	0.977918	0.667313	0.044*
C6	0.62892 (12)	0.9373 (3)	0.75841 (10)	0.0376 (3)
H6	0.623008	1.068842	0.802484	0.045*
C7	0.72273 (11)	0.8005 (3)	0.77643 (9)	0.0344 (3)
C8	0.73236 (11)	0.6072 (3)	0.71137 (10)	0.0352 (3)
H8	0.794532	0.513265	0.722420	0.042*
C9	0.81092 (12)	0.8590 (3)	0.86743 (10)	0.0379 (3)
H9A	0.801955	1.036134	0.890701	0.046*
H9B	0.876071	0.856506	0.851211	0.046*
C10	0.81734 (13)	0.6621 (3)	0.94856 (10)	0.0394 (3)
H10A	0.750354	0.655765	0.961239	0.047*
H10B	0.830748	0.486836	0.926457	0.047*
C11	0.90121 (12)	0.7263 (3)	1.04376 (9)	0.0362 (3)
H11A	0.967540	0.747249	1.030556	0.043*
H11B	0.884661	0.893763	1.069536	0.043*
C12	0.91109 (12)	0.5142 (3)	1.11922 (10)	0.0392 (3)
H12A	0.845080	0.493447	1.133053	0.047*
H12B	0.927885	0.346444	1.093882	0.047*
O13	0.98987 (9)	0.5799 (2)	1.20676 (7)	0.0442 (3)
H13	0.9982 (13)	0.461 (4)	1.2439 (14)	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03197 (18)	0.0430 (2)	0.03142 (18)	0.00506 (12)	0.00521 (13)	−0.00803 (12)
C2	0.0327 (6)	0.0350 (6)	0.0256 (5)	−0.0006 (5)	0.0079 (4)	−0.0017 (5)
C3	0.0322 (6)	0.0333 (6)	0.0255 (5)	−0.0017 (5)	0.0084 (4)	−0.0015 (4)
C4	0.0302 (5)	0.0354 (6)	0.0264 (5)	0.0004 (5)	0.0072 (4)	−0.0018 (5)
C5	0.0376 (7)	0.0395 (7)	0.0313 (6)	0.0010 (5)	0.0086 (5)	−0.0067 (5)
C6	0.0442 (7)	0.0384 (7)	0.0287 (6)	−0.0040 (6)	0.0089 (5)	−0.0067 (5)
C7	0.0387 (7)	0.0372 (7)	0.0245 (5)	−0.0081 (5)	0.0054 (5)	0.0000 (5)
C8	0.0334 (6)	0.0400 (7)	0.0295 (6)	−0.0015 (5)	0.0053 (5)	−0.0015 (5)
C9	0.0422 (7)	0.0380 (7)	0.0279 (6)	−0.0100 (6)	0.0020 (5)	−0.0008 (5)
C10	0.0486 (8)	0.0322 (7)	0.0291 (6)	−0.0091 (6)	−0.0006 (5)	−0.0009 (5)
C11	0.0436 (7)	0.0308 (6)	0.0278 (6)	−0.0054 (5)	0.0014 (5)	−0.0021 (5)
C12	0.0483 (8)	0.0324 (7)	0.0291 (6)	−0.0041 (6)	0.0001 (5)	−0.0010 (5)
O13	0.0516 (6)	0.0404 (6)	0.0297 (5)	−0.0019 (5)	−0.0040 (4)	0.0003 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7316 (14)	C9—C10	1.517 (2)
S1—C2	1.7486 (13)	C9—H9A	0.9800
C2—C8	1.3987 (18)	C9—H9B	0.9800
C2—C3	1.4074 (18)	C10—C11	1.5258 (19)
C3—C5	1.3954 (18)	C10—H10A	0.9800
C3—C4	1.4364 (17)	C10—H10B	0.9800
C4—C4ⁱ	1.370 (3)	C11—C12	1.505 (2)
C5—C6	1.3840 (19)	C11—H11A	0.9800
C5—H5	0.9400	C11—H11B	0.9800
C6—C7	1.404 (2)	C12—O13	1.4213 (16)
C6—H6	0.9400	C12—H12A	0.9800
C7—C8	1.388 (2)	C12—H12B	0.9800
C7—C9	1.5103 (19)	O13—H13	0.79 (3)
C8—H8	0.9400

C4ⁱ—S1—C2	90.62 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.43 (12)	C7—C9—H9B	109.1
C8—C2—S1	125.62 (11)	C10—C9—H9B	109.1
C3—C2—S1	112.95 (9)	H9A—C9—H9B	107.9
C5—C3—C2	119.22 (12)	C11—C10—C9	113.61 (12)
C5—C3—C4	131.05 (13)	C11—C10—H10A	108.8
C2—C3—C4	109.73 (11)	C9—C10—H10A	108.8
C4ⁱ—C4—C3	114.19 (15)	C11—C10—H10B	108.8
C4ⁱ—C4—S1ⁱ	112.51 (13)	C9—C10—H10B	108.8
C3—C4—S1ⁱ	133.30 (10)	H10A—C10—H10B	107.7
C6—C5—C3	119.02 (13)	C12—C11—C10	111.81 (12)
C6—C5—H5	120.5	C12—C11—H11A	109.3
C3—C5—H5	120.5	C10—C11—H11A	109.3
C5—C6—C7	121.99 (13)	C12—C11—H11B	109.3
C5—C6—H6	119.0	C10—C11—H11B	109.3
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.39 (12)	O13—C12—C11	110.35 (12)
C8—C7—C9	120.64 (14)	O13—C12—H12A	109.6
C6—C7—C9	119.95 (13)	C11—C12—H12A	109.6
C2—C8—C7	118.95 (13)	O13—C12—H12B	109.6
C2—C8—H8	120.5	C11—C12—H12B	109.6
C7—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.39 (12)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.66 (13)	C3—C5—C6—C7	−0.3 (2)
C4ⁱ—S1—C2—C3	−0.58 (11)	C5—C6—C7—C8	0.4 (2)
C8—C2—C3—C5	1.1 (2)	C5—C6—C7—C9	−177.84 (13)
S1—C2—C3—C5	−178.72 (11)	C3—C2—C8—C7	−1.0 (2)
C8—C2—C3—C4	−179.74 (12)	S1—C2—C8—C7	178.77 (11)
S1—C2—C3—C4	0.49 (15)	C6—C7—C8—C2	0.2 (2)
C5—C3—C4—C4ⁱ	178.99 (16)	C9—C7—C8—C2	178.49 (13)
C2—C3—C4—C4ⁱ	−0.1 (2)	C8—C7—C9—C10	−79.95 (18)
C5—C3—C4—S1ⁱ	−1.4 (2)	C6—C7—C9—C10	98.31 (17)
C2—C3—C4—S1ⁱ	179.47 (11)	C7—C9—C10—C11	−176.15 (14)
C2—C3—C5—C6	−0.4 (2)	C9—C10—C11—C12	−175.02 (14)
C4—C3—C5—C6	−179.40 (14)	C10—C11—C12—O13	179.89 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.79	2.05	2.8030 (9)	159
C6—H6···S1ⁱⁱⁱ	0.94	3.35	4.1336 (15)	143
C9—H9A···S1ⁱⁱⁱ	0.98	3.49	4.1132 (18)	124
C10—H10A···S1ⁱⁱⁱ	0.98	3.34	3.9594 (18)	123
C10—H10A···S1^iv	0.98	3.18	3.8657 (16)	129
C11—H11B···S1ⁱⁱⁱ	0.98	3.44	4.1275 (17)	129
C12—H12A···S1^iv	0.98	3.08	3.8330 (17)	134

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A220) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.587 (2) Å	Cell parameters from 6932 reflections
b = 5.077 (1) Å	θ = 2.2–25.5°
c = 14.368 (2) Å	µ = 0.28 mm⁻¹
β = 107.690 (16)°	T = 220 K
V = 944.3 (2) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.024
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8507 measured reflections	h = −19→19
2798 independent reflections	k = −6→7
2563 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.067P)² + 0.2715P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2798 reflections	Δρ_max = 0.70 e Å⁻³
121 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.034 (4)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64601 (2)	0.32374 (7)	0.53824 (2)	0.03750 (13)
C2	0.64812 (9)	0.5542 (3)	0.62923 (8)	0.0320 (2)
C3	0.55384 (9)	0.6901 (2)	0.61200 (9)	0.0314 (2)
C4	0.48110 (9)	0.5966 (2)	0.52319 (8)	0.0315 (2)
C5	0.54487 (10)	0.8842 (3)	0.67770 (9)	0.0377 (3)
H5	0.482728	0.977647	0.667287	0.045*
C6	0.62874 (11)	0.9370 (3)	0.75832 (9)	0.0386 (3)
H6	0.622805	1.068372	0.802394	0.046*
C7	0.72264 (10)	0.8003 (3)	0.77644 (9)	0.0353 (3)
C8	0.73220 (10)	0.6073 (3)	0.71140 (9)	0.0362 (3)
H8	0.794373	0.513635	0.722444	0.043*
C9	0.81079 (11)	0.8587 (3)	0.86744 (9)	0.0393 (3)
H9A	0.801869	1.035996	0.890656	0.047*
H9B	0.875863	0.856155	0.851293	0.047*
C10	0.81719 (12)	0.6618 (3)	0.94856 (10)	0.0407 (3)
H10A	0.750259	0.655548	0.961140	0.049*
H10B	0.830581	0.486499	0.926527	0.049*
C11	0.90099 (11)	0.7262 (3)	1.04378 (9)	0.0370 (3)
H11A	0.967238	0.747350	1.030654	0.044*
H11B	0.884400	0.893579	1.069529	0.044*
C12	0.91101 (11)	0.5143 (3)	1.11913 (9)	0.0403 (3)
H12A	0.845051	0.493148	1.132798	0.048*
H12B	0.927936	0.346664	1.093839	0.048*
O13	0.98962 (9)	0.5801 (2)	1.20679 (7)	0.0458 (3)
H13	0.9986 (13)	0.459 (4)	1.2442 (13)	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03189 (18)	0.0447 (2)	0.03289 (18)	0.00539 (11)	0.00540 (12)	−0.00829 (11)
C2	0.0331 (5)	0.0357 (6)	0.0268 (5)	−0.0007 (4)	0.0083 (4)	−0.0017 (4)
C3	0.0327 (5)	0.0344 (6)	0.0272 (5)	−0.0019 (4)	0.0092 (4)	−0.0020 (4)
C4	0.0300 (5)	0.0365 (6)	0.0272 (5)	0.0001 (4)	0.0073 (4)	−0.0019 (4)
C5	0.0382 (6)	0.0411 (7)	0.0329 (6)	0.0011 (5)	0.0094 (5)	−0.0067 (5)
C6	0.0442 (7)	0.0402 (7)	0.0301 (5)	−0.0038 (5)	0.0091 (5)	−0.0070 (5)
C7	0.0383 (6)	0.0386 (6)	0.0259 (5)	−0.0083 (5)	0.0053 (4)	0.0002 (4)
C8	0.0330 (6)	0.0422 (7)	0.0306 (5)	−0.0016 (5)	0.0053 (4)	−0.0015 (5)
C9	0.0428 (7)	0.0400 (7)	0.0292 (5)	−0.0104 (5)	0.0023 (5)	−0.0012 (5)
C10	0.0495 (7)	0.0336 (6)	0.0304 (6)	−0.0093 (5)	−0.0005 (5)	−0.0009 (4)
C11	0.0438 (6)	0.0316 (6)	0.0294 (5)	−0.0055 (5)	0.0020 (5)	−0.0025 (4)
C12	0.0487 (7)	0.0339 (6)	0.0302 (5)	−0.0043 (5)	−0.0002 (5)	−0.0012 (5)
O13	0.0535 (6)	0.0414 (5)	0.0310 (4)	−0.0024 (4)	−0.0046 (4)	0.0003 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7318 (12)	C9—C10	1.5180 (19)
S1—C2	1.7481 (12)	C9—H9A	0.9800
C2—C8	1.3971 (16)	C9—H9B	0.9800
C2—C3	1.4093 (17)	C10—C11	1.5260 (18)
C3—C5	1.3953 (17)	C10—H10A	0.9800
C3—C4	1.4367 (16)	C10—H10B	0.9800
C4—C4ⁱ	1.370 (2)	C11—C12	1.5026 (18)
C5—C6	1.3820 (17)	C11—H11A	0.9800
C5—H5	0.9400	C11—H11B	0.9800
C6—C7	1.405 (2)	C12—O13	1.4217 (15)
C6—H6	0.9400	C12—H12A	0.9800
C7—C8	1.3869 (18)	C12—H12B	0.9800
C7—C9	1.5101 (17)	O13—H13	0.80 (2)
C8—H8	0.9400

C4ⁱ—S1—C2	90.69 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.33 (11)	C7—C9—H9B	109.1
C8—C2—S1	125.78 (10)	C10—C9—H9B	109.1
C3—C2—S1	112.89 (9)	H9A—C9—H9B	107.9
C5—C3—C2	119.25 (11)	C11—C10—C9	113.59 (11)
C5—C3—C4	131.03 (11)	C11—C10—H10A	108.8
C2—C3—C4	109.72 (11)	C9—C10—H10A	108.8
C4ⁱ—C4—C3	114.22 (13)	C11—C10—H10B	108.8
C4ⁱ—C4—S1ⁱ	112.48 (12)	C9—C10—H10B	108.8
C3—C4—S1ⁱ	133.30 (9)	H10A—C10—H10B	107.7
C6—C5—C3	118.99 (12)	C12—C11—C10	111.84 (11)
C6—C5—H5	120.5	C12—C11—H11A	109.2
C3—C5—H5	120.5	C10—C11—H11A	109.2
C5—C6—C7	122.03 (12)	C12—C11—H11B	109.2
C5—C6—H6	119.0	C10—C11—H11B	109.2
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.31 (11)	O13—C12—C11	110.44 (11)
C8—C7—C9	120.68 (13)	O13—C12—H12A	109.6
C6—C7—C9	119.99 (12)	C11—C12—H12A	109.6
C2—C8—C7	119.07 (12)	O13—C12—H12B	109.6
C2—C8—H8	120.5	C11—C12—H12B	109.6
C7—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.37 (11)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.80 (12)	C3—C5—C6—C7	−0.3 (2)
C4ⁱ—S1—C2—C3	−0.61 (10)	C5—C6—C7—C8	0.4 (2)
C8—C2—C3—C5	0.89 (19)	C5—C6—C7—C9	−177.87 (12)
S1—C2—C3—C5	−178.72 (10)	C3—C2—C8—C7	−0.8 (2)
C8—C2—C3—C4	−179.81 (11)	S1—C2—C8—C7	178.76 (10)
S1—C2—C3—C4	0.58 (13)	C6—C7—C8—C2	0.1 (2)
C5—C3—C4—C4ⁱ	178.96 (15)	C9—C7—C8—C2	178.43 (12)
C2—C3—C4—C4ⁱ	−0.22 (19)	C8—C7—C9—C10	−80.06 (17)
C5—C3—C4—S1ⁱ	−1.3 (2)	C6—C7—C9—C10	98.21 (16)
C2—C3—C4—S1ⁱ	179.48 (10)	C7—C9—C10—C11	−176.12 (13)
C2—C3—C5—C6	−0.3 (2)	C9—C10—C11—C12	−174.93 (13)
C4—C3—C5—C6	−179.44 (13)	C10—C11—C12—O13	179.97 (12)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.80	2.04	2.8022 (8)	160
C6—H6···S1ⁱⁱⁱ	0.94	3.35	4.1392 (14)	143
C9—H9A···S1ⁱⁱⁱ	0.98	3.50	4.1198 (17)	124
C10—H10A···S1ⁱⁱⁱ	0.98	3.34	3.9639 (17)	123
C10—H10A···S1^iv	0.98	3.18	3.8687 (15)	129
C11—H11B···S1ⁱⁱⁱ	0.98	3.44	4.1306 (16)	129
C12—H12A···S1^iv	0.98	3.08	3.8364 (15)	135

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A230) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.350 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.606 (2) Å	Cell parameters from 6988 reflections
b = 5.077 (1) Å	θ = 2.2–24.4°
c = 14.379 (2) Å	µ = 0.28 mm⁻¹
β = 107.770 (18)°	T = 230 K
V = 945.9 (2) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.024
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8516 measured reflections	h = −19→19
2802 independent reflections	k = −6→7
2550 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0726P)² + 0.2488P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
2802 reflections	Δρ_max = 0.67 e Å⁻³
121 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.038 (5)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64588 (2)	0.32379 (7)	0.53831 (2)	0.03939 (14)
C2	0.64803 (9)	0.5542 (3)	0.62927 (8)	0.0336 (2)
C3	0.55384 (10)	0.6899 (2)	0.61204 (9)	0.0328 (2)
C4	0.48108 (9)	0.5966 (3)	0.52318 (8)	0.0330 (2)
C5	0.54490 (11)	0.8838 (3)	0.67762 (10)	0.0395 (3)
H5	0.482848	0.977374	0.667102	0.047*
C6	0.62881 (11)	0.9364 (3)	0.75848 (9)	0.0405 (3)
H6	0.622839	1.067370	0.802644	0.049*
C7	0.72250 (11)	0.8001 (3)	0.77653 (9)	0.0371 (3)
C8	0.73210 (10)	0.6071 (3)	0.71146 (9)	0.0382 (3)
H8	0.794212	0.513466	0.722520	0.046*
C9	0.81070 (12)	0.8586 (3)	0.86742 (10)	0.0412 (3)
H9A	0.801942	1.035979	0.890561	0.049*
H9B	0.875649	0.855524	0.851275	0.049*
C10	0.81706 (12)	0.6615 (3)	0.94872 (10)	0.0424 (3)
H10A	0.750247	0.655763	0.961305	0.051*
H10B	0.830288	0.486078	0.926764	0.051*
C11	0.90089 (11)	0.7260 (3)	1.04379 (9)	0.0390 (3)
H11A	0.967019	0.746800	1.030625	0.047*
H11B	0.884450	0.893533	1.069466	0.047*
C12	0.91095 (12)	0.5147 (3)	1.11910 (10)	0.0423 (3)
H12A	0.845072	0.493758	1.132744	0.051*
H12B	0.927731	0.346870	1.093862	0.051*
O13	0.98953 (9)	0.5802 (2)	1.20674 (7)	0.0481 (3)
H13	0.9976 (13)	0.457 (4)	1.2457 (13)	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03333 (19)	0.0470 (2)	0.03469 (19)	0.00566 (11)	0.00573 (13)	−0.00871 (12)
C2	0.0347 (5)	0.0372 (6)	0.0281 (5)	−0.0006 (4)	0.0086 (4)	−0.0015 (4)
C3	0.0342 (5)	0.0362 (6)	0.0278 (5)	−0.0021 (4)	0.0092 (4)	−0.0018 (4)
C4	0.0311 (5)	0.0383 (6)	0.0286 (5)	0.0004 (4)	0.0077 (4)	−0.0022 (4)
C5	0.0401 (6)	0.0429 (7)	0.0343 (6)	0.0011 (5)	0.0098 (5)	−0.0067 (5)
C6	0.0457 (7)	0.0424 (7)	0.0317 (6)	−0.0040 (5)	0.0093 (5)	−0.0074 (5)
C7	0.0404 (6)	0.0403 (6)	0.0275 (5)	−0.0091 (5)	0.0058 (4)	−0.0003 (4)
C8	0.0343 (6)	0.0445 (7)	0.0329 (6)	−0.0021 (5)	0.0058 (4)	−0.0022 (5)
C9	0.0448 (7)	0.0418 (7)	0.0306 (5)	−0.0113 (5)	0.0021 (5)	−0.0010 (5)
C10	0.0513 (8)	0.0355 (6)	0.0313 (6)	−0.0099 (5)	−0.0008 (5)	−0.0012 (5)
C11	0.0459 (7)	0.0333 (6)	0.0313 (6)	−0.0059 (5)	0.0022 (5)	−0.0026 (5)
C12	0.0509 (7)	0.0356 (6)	0.0319 (6)	−0.0046 (5)	−0.0002 (5)	−0.0014 (5)
O13	0.0557 (6)	0.0435 (6)	0.0326 (5)	−0.0024 (5)	−0.0050 (4)	0.0002 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7311 (13)	C9—C10	1.5208 (19)
S1—C2	1.7484 (13)	C9—H9A	0.9800
C2—C8	1.3971 (17)	C9—H9B	0.9800
C2—C3	1.4089 (17)	C10—C11	1.5248 (18)
C3—C5	1.3937 (17)	C10—H10A	0.9800
C3—C4	1.4371 (16)	C10—H10B	0.9800
C4—C4ⁱ	1.371 (2)	C11—C12	1.5006 (19)
C5—C6	1.3843 (18)	C11—H11A	0.9800
C5—H5	0.9400	C11—H11B	0.9800
C6—C7	1.403 (2)	C12—O13	1.4210 (16)
C6—H6	0.9400	C12—H12A	0.9800
C7—C8	1.3881 (19)	C12—H12B	0.9800
C7—C9	1.5096 (18)	O13—H13	0.82 (2)
C8—H8	0.9400

C4ⁱ—S1—C2	90.69 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.38 (12)	C7—C9—H9B	109.1
C8—C2—S1	125.72 (10)	C10—C9—H9B	109.1
C3—C2—S1	112.90 (9)	H9A—C9—H9B	107.9
C5—C3—C2	119.27 (11)	C11—C10—C9	113.55 (11)
C5—C3—C4	130.98 (12)	C11—C10—H10A	108.9
C2—C3—C4	109.74 (11)	C9—C10—H10A	108.9
C4ⁱ—C4—C3	114.15 (14)	C11—C10—H10B	108.9
C4ⁱ—C4—S1ⁱ	112.51 (12)	C9—C10—H10B	108.9
C3—C4—S1ⁱ	133.34 (10)	H10A—C10—H10B	107.7
C6—C5—C3	118.99 (13)	C12—C11—C10	111.84 (11)
C6—C5—H5	120.5	C12—C11—H11A	109.2
C3—C5—H5	120.5	C10—C11—H11A	109.2
C5—C6—C7	122.00 (12)	C12—C11—H11B	109.2
C5—C6—H6	119.0	C10—C11—H11B	109.2
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.36 (12)	O13—C12—C11	110.54 (11)
C8—C7—C9	120.59 (13)	O13—C12—H12A	109.5
C6—C7—C9	120.02 (12)	C11—C12—H12A	109.5
C2—C8—C7	118.99 (13)	O13—C12—H12B	109.5
C2—C8—H8	120.5	C11—C12—H12B	109.5
C7—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.33 (11)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.78 (13)	C3—C5—C6—C7	−0.1 (2)
C4ⁱ—S1—C2—C3	−0.55 (10)	C5—C6—C7—C8	0.3 (2)
C8—C2—C3—C5	0.97 (19)	C5—C6—C7—C9	−178.06 (13)
S1—C2—C3—C5	−178.71 (10)	C3—C2—C8—C7	−0.8 (2)
C8—C2—C3—C4	−179.80 (12)	S1—C2—C8—C7	178.80 (10)
S1—C2—C3—C4	0.52 (14)	C6—C7—C8—C2	0.2 (2)
C5—C3—C4—C4ⁱ	178.92 (15)	C9—C7—C8—C2	178.53 (12)
C2—C3—C4—C4ⁱ	−0.19 (19)	C8—C7—C9—C10	−80.28 (17)
C5—C3—C4—S1ⁱ	−1.4 (2)	C6—C7—C9—C10	98.02 (16)
C2—C3—C4—S1ⁱ	179.52 (11)	C7—C9—C10—C11	−176.12 (13)
C2—C3—C5—C6	−0.5 (2)	C9—C10—C11—C12	−174.90 (13)
C4—C3—C5—C6	−179.51 (13)	C10—C11—C12—O13	180.00 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.82	2.02	2.8030 (9)	158
C6—H6···S1ⁱⁱⁱ	0.94	3.35	4.1419 (14)	143
C9—H9A···S1ⁱⁱⁱ	0.98	3.50	4.1268 (17)	124
C10—H10A···S1ⁱⁱⁱ	0.98	3.34	3.9677 (18)	123
C10—H10A···S1^iv	0.98	3.18	3.8713 (16)	129
C11—H11B···S1ⁱⁱⁱ	0.98	3.45	4.1356 (16)	129
C12—H12A···S1^iv	0.98	3.09	3.8409 (16)	135

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A240) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.348 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.625 (2) Å	Cell parameters from 6920 reflections
b = 5.076 (1) Å	θ = 2.5–24.5°
c = 14.392 (2) Å	µ = 0.28 mm⁻¹
β = 107.852 (19)°	T = 240 K
V = 947.4 (2) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.026
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8471 measured reflections	h = −19→19
2793 independent reflections	k = −6→7
2534 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.121	w = 1/[σ²(F_o²) + (0.0699P)² + 0.272P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
2793 reflections	Δρ_max = 0.65 e Å⁻³
121 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.036 (5)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64574 (2)	0.32381 (7)	0.53835 (2)	0.04124 (14)
C2	0.64790 (10)	0.5542 (3)	0.62927 (9)	0.0351 (3)
C3	0.55388 (10)	0.6896 (3)	0.61211 (9)	0.0343 (3)
C4	0.48115 (9)	0.5965 (3)	0.52315 (9)	0.0345 (3)
C5	0.54499 (11)	0.8832 (3)	0.67771 (10)	0.0412 (3)
H5	0.482972	0.976699	0.667220	0.049*
C6	0.62887 (11)	0.9358 (3)	0.75855 (9)	0.0424 (3)
H6	0.622970	1.066688	0.802731	0.051*
C7	0.72235 (11)	0.7997 (3)	0.77650 (9)	0.0391 (3)
C8	0.73185 (10)	0.6072 (3)	0.71158 (10)	0.0398 (3)
H8	0.793896	0.513433	0.722733	0.048*
C9	0.81049 (12)	0.8580 (3)	0.86756 (10)	0.0431 (3)
H9A	0.801692	1.035384	0.890703	0.052*
H9B	0.875372	0.855275	0.851498	0.052*
C10	0.81710 (13)	0.6614 (3)	0.94869 (10)	0.0448 (3)
H10A	0.750353	0.655163	0.961169	0.054*
H10B	0.830475	0.486048	0.926791	0.054*
C11	0.90075 (12)	0.7261 (3)	1.04380 (9)	0.0410 (3)
H11A	0.966805	0.747367	1.030771	0.049*
H11B	0.884166	0.893495	1.069443	0.049*
C12	0.91094 (12)	0.5146 (3)	1.11903 (10)	0.0445 (3)
H12A	0.845120	0.493116	1.132504	0.053*
H12B	0.927933	0.346975	1.093859	0.053*
O13	0.98933 (9)	0.5806 (2)	1.20674 (7)	0.0506 (3)
H13	0.9983 (14)	0.457 (4)	1.2449 (14)	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03491 (19)	0.0493 (2)	0.03614 (19)	0.00581 (12)	0.00589 (13)	−0.00905 (12)
C2	0.0362 (6)	0.0392 (6)	0.0293 (5)	−0.0012 (5)	0.0090 (4)	−0.0018 (4)
C3	0.0361 (6)	0.0375 (6)	0.0293 (5)	−0.0023 (4)	0.0099 (4)	−0.0017 (4)
C4	0.0327 (5)	0.0401 (6)	0.0296 (5)	0.0002 (4)	0.0081 (4)	−0.0021 (4)
C5	0.0418 (6)	0.0443 (7)	0.0360 (6)	0.0014 (5)	0.0099 (5)	−0.0069 (5)
C6	0.0485 (7)	0.0437 (7)	0.0332 (6)	−0.0039 (5)	0.0099 (5)	−0.0075 (5)
C7	0.0427 (6)	0.0425 (7)	0.0288 (5)	−0.0095 (5)	0.0059 (5)	0.0002 (5)
C8	0.0359 (6)	0.0463 (7)	0.0337 (6)	−0.0019 (5)	0.0056 (5)	−0.0017 (5)
C9	0.0468 (7)	0.0439 (7)	0.0320 (6)	−0.0116 (6)	0.0022 (5)	−0.0013 (5)
C10	0.0547 (8)	0.0373 (7)	0.0329 (6)	−0.0100 (6)	−0.0004 (5)	−0.0012 (5)
C11	0.0478 (7)	0.0358 (6)	0.0325 (6)	−0.0060 (5)	0.0020 (5)	−0.0028 (5)
C12	0.0530 (8)	0.0377 (7)	0.0335 (6)	−0.0049 (6)	−0.0004 (5)	−0.0014 (5)
O13	0.0581 (6)	0.0463 (6)	0.0344 (5)	−0.0024 (5)	−0.0052 (4)	0.0000 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7313 (13)	C9—C10	1.517 (2)
S1—C2	1.7485 (13)	C9—H9A	0.9800
C2—C8	1.3975 (17)	C9—H9B	0.9800
C2—C3	1.4071 (18)	C10—C11	1.5244 (18)
C3—C5	1.3938 (18)	C10—H10A	0.9800
C3—C4	1.4375 (16)	C10—H10B	0.9800
C4—C4ⁱ	1.370 (2)	C11—C12	1.500 (2)
C5—C6	1.3841 (18)	C11—H11A	0.9800
C5—H5	0.9400	C11—H11B	0.9800
C6—C7	1.402 (2)	C12—O13	1.4212 (16)
C6—H6	0.9400	C12—H12A	0.9800
C7—C8	1.385 (2)	C12—H12B	0.9800
C7—C9	1.5107 (18)	O13—H13	0.82 (3)
C8—H8	0.9400

C4ⁱ—S1—C2	90.66 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.29 (12)	C7—C9—H9B	109.1
C8—C2—S1	125.77 (10)	C10—C9—H9B	109.1
C3—C2—S1	112.93 (9)	H9A—C9—H9B	107.8
C5—C3—C2	119.27 (12)	C11—C10—C9	113.64 (11)
C5—C3—C4	130.97 (12)	C11—C10—H10A	108.8
C2—C3—C4	109.75 (11)	C9—C10—H10A	108.8
C4ⁱ—C4—C3	114.15 (14)	C11—C10—H10B	108.8
C4ⁱ—C4—S1ⁱ	112.51 (12)	C9—C10—H10B	108.8
C3—C4—S1ⁱ	133.34 (10)	H10A—C10—H10B	107.7
C6—C5—C3	118.98 (13)	C12—C11—C10	111.85 (11)
C6—C5—H5	120.5	C12—C11—H11A	109.2
C3—C5—H5	120.5	C10—C11—H11A	109.2
C5—C6—C7	121.98 (13)	C12—C11—H11B	109.2
C5—C6—H6	119.0	C10—C11—H11B	109.2
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.40 (12)	O13—C12—C11	110.51 (12)
C8—C7—C9	120.63 (13)	O13—C12—H12A	109.5
C6—C7—C9	119.95 (13)	C11—C12—H12A	109.5
C2—C8—C7	119.07 (13)	O13—C12—H12B	109.5
C2—C8—H8	120.5	C11—C12—H12B	109.5
C7—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.50 (11)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.69 (13)	C3—C5—C6—C7	−0.2 (2)
C4ⁱ—S1—C2—C3	−0.47 (10)	C5—C6—C7—C8	0.2 (2)
C8—C2—C3—C5	1.1 (2)	C5—C6—C7—C9	−177.94 (13)
S1—C2—C3—C5	−178.76 (10)	C3—C2—C8—C7	−1.0 (2)
C8—C2—C3—C4	−179.79 (12)	S1—C2—C8—C7	178.82 (10)
S1—C2—C3—C4	0.36 (14)	C6—C7—C8—C2	0.3 (2)
C5—C3—C4—C4ⁱ	178.97 (15)	C9—C7—C8—C2	178.51 (12)
C2—C3—C4—C4ⁱ	0.0 (2)	C8—C7—C9—C10	−80.18 (18)
C5—C3—C4—S1ⁱ	−1.5 (2)	C6—C7—C9—C10	97.98 (17)
C2—C3—C4—S1ⁱ	179.55 (11)	C7—C9—C10—C11	−176.05 (14)
C2—C3—C5—C6	−0.5 (2)	C9—C10—C11—C12	−174.89 (14)
C4—C3—C5—C6	−179.40 (14)	C10—C11—C12—O13	−179.95 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.82	2.02	2.8026 (9)	159
C6—H6···S1ⁱⁱⁱ	0.94	3.36	4.1462 (14)	143
C9—H9A···S1ⁱⁱⁱ	0.98	3.51	4.1319 (18)	124
C10—H10A···S1ⁱⁱⁱ	0.98	3.35	3.9738 (18)	123
C10—H10A···S1^iv	0.98	3.19	3.8769 (16)	129
C11—H11B···S1ⁱⁱⁱ	0.98	3.45	4.1390 (17)	129
C12—H12A···S1^iv	0.98	3.09	3.8449 (16)	135

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A250) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.644 (3) Å	Cell parameters from 7096 reflections
b = 5.076 (1) Å	θ = 2.3–25.4°
c = 14.405 (3) Å	µ = 0.28 mm⁻¹
β = 107.94 (2)°	T = 250 K
V = 949.2 (3) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.024
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.6°
8491 measured reflections	h = −19→19
2806 independent reflections	k = −6→7
2530 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0676P)² + 0.277P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
2806 reflections	Δρ_max = 0.63 e Å⁻³
121 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.035 (5)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64559 (2)	0.32387 (7)	0.53841 (2)	0.04310 (13)
C2	0.64784 (10)	0.5539 (3)	0.62938 (9)	0.0366 (3)
C3	0.55390 (10)	0.6894 (2)	0.61213 (9)	0.0357 (3)
C4	0.48125 (9)	0.5965 (3)	0.52311 (9)	0.0359 (3)
C5	0.54503 (11)	0.8828 (3)	0.67774 (10)	0.0431 (3)
H5	0.483029	0.975985	0.667263	0.052*
C6	0.62877 (11)	0.9354 (3)	0.75848 (10)	0.0445 (3)
H6	0.622903	1.066465	0.802569	0.053*
C7	0.72223 (11)	0.7992 (3)	0.77659 (9)	0.0407 (3)
C8	0.73177 (10)	0.6068 (3)	0.71171 (10)	0.0417 (3)
H8	0.793780	0.513202	0.722894	0.050*
C9	0.81036 (12)	0.8577 (3)	0.86769 (10)	0.0452 (3)
H9A	0.801534	1.035079	0.890795	0.054*
H9B	0.875157	0.855083	0.851700	0.054*
C10	0.81702 (13)	0.6614 (3)	0.94865 (10)	0.0462 (3)
H10A	0.750358	0.655168	0.961058	0.055*
H10B	0.830334	0.486049	0.926736	0.055*
C11	0.90064 (12)	0.7258 (3)	1.04380 (9)	0.0427 (3)
H11A	0.966632	0.746757	1.030849	0.051*
H11B	0.884179	0.893311	1.069373	0.051*
C12	0.91084 (12)	0.5148 (3)	1.11903 (10)	0.0468 (3)
H12A	0.845110	0.493654	1.132482	0.056*
H12B	0.927710	0.347017	1.093954	0.056*
O13	0.98922 (9)	0.5808 (2)	1.20666 (8)	0.0528 (3)
H13	0.9979 (13)	0.457 (4)	1.2453 (13)	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.03661 (19)	0.0514 (2)	0.03782 (19)	0.00608 (12)	0.00634 (13)	−0.00933 (13)
C2	0.0376 (6)	0.0409 (6)	0.0304 (5)	−0.0010 (5)	0.0092 (4)	−0.0019 (4)
C3	0.0378 (6)	0.0388 (6)	0.0305 (5)	−0.0024 (4)	0.0105 (4)	−0.0020 (4)
C4	0.0341 (5)	0.0415 (6)	0.0310 (5)	0.0004 (5)	0.0086 (4)	−0.0019 (5)
C5	0.0438 (7)	0.0472 (7)	0.0367 (6)	0.0014 (5)	0.0100 (5)	−0.0076 (5)
C6	0.0511 (7)	0.0461 (7)	0.0344 (6)	−0.0049 (6)	0.0105 (5)	−0.0079 (5)
C7	0.0443 (7)	0.0443 (7)	0.0300 (5)	−0.0097 (5)	0.0063 (5)	0.0000 (5)
C8	0.0378 (6)	0.0480 (7)	0.0357 (6)	−0.0020 (5)	0.0063 (5)	−0.0019 (5)
C9	0.0491 (7)	0.0460 (7)	0.0336 (6)	−0.0119 (6)	0.0027 (5)	−0.0014 (5)
C10	0.0559 (8)	0.0387 (7)	0.0344 (6)	−0.0099 (6)	−0.0005 (5)	−0.0015 (5)
C11	0.0498 (7)	0.0373 (6)	0.0341 (6)	−0.0062 (5)	0.0025 (5)	−0.0030 (5)
C12	0.0555 (8)	0.0397 (7)	0.0354 (6)	−0.0053 (6)	−0.0006 (5)	−0.0016 (5)
O13	0.0611 (7)	0.0475 (6)	0.0361 (5)	−0.0024 (5)	−0.0053 (4)	−0.0002 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7318 (13)	C9—C10	1.515 (2)
S1—C2	1.7483 (13)	C9—H9A	0.9800
C2—C8	1.3977 (17)	C9—H9B	0.9800
C2—C3	1.4076 (18)	C10—C11	1.5244 (19)
C3—C5	1.3935 (18)	C10—H10A	0.9800
C3—C4	1.4375 (17)	C10—H10B	0.9800
C4—C4ⁱ	1.369 (2)	C11—C12	1.499 (2)
C5—C6	1.3825 (19)	C11—H11A	0.9800
C5—H5	0.9400	C11—H11B	0.9800
C6—C7	1.403 (2)	C12—O13	1.4206 (16)
C6—H6	0.9400	C12—H12A	0.9800
C7—C8	1.385 (2)	C12—H12B	0.9800
C7—C9	1.5114 (18)	O13—H13	0.82 (3)
C8—H8	0.9400

C4ⁱ—S1—C2	90.67 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.29 (12)	C7—C9—H9B	109.1
C8—C2—S1	125.80 (11)	C10—C9—H9B	109.1
C3—C2—S1	112.90 (9)	H9A—C9—H9B	107.8
C5—C3—C2	119.28 (12)	C11—C10—C9	113.71 (12)
C5—C3—C4	130.99 (12)	C11—C10—H10A	108.8
C2—C3—C4	109.72 (11)	C9—C10—H10A	108.8
C4ⁱ—C4—C3	114.21 (14)	C11—C10—H10B	108.8
C4ⁱ—C4—S1ⁱ	112.49 (12)	C9—C10—H10B	108.8
C3—C4—S1ⁱ	133.30 (10)	H10A—C10—H10B	107.7
C6—C5—C3	119.00 (13)	C12—C11—C10	111.97 (12)
C6—C5—H5	120.5	C12—C11—H11A	109.2
C3—C5—H5	120.5	C10—C11—H11A	109.2
C5—C6—C7	121.99 (13)	C12—C11—H11B	109.2
C5—C6—H6	119.0	C10—C11—H11B	109.2
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.40 (12)	O13—C12—C11	110.54 (12)
C8—C7—C9	120.62 (13)	O13—C12—H12A	109.5
C6—C7—C9	119.95 (13)	C11—C12—H12A	109.5
C2—C8—C7	119.03 (13)	O13—C12—H12B	109.5
C2—C8—H8	120.5	C11—C12—H12B	109.5
C7—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.48 (12)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.71 (13)	C3—C5—C6—C7	−0.3 (2)
C4ⁱ—S1—C2—C3	−0.57 (10)	C5—C6—C7—C8	0.4 (2)
C8—C2—C3—C5	1.0 (2)	C5—C6—C7—C9	−177.93 (13)
S1—C2—C3—C5	−178.76 (10)	C3—C2—C8—C7	−0.9 (2)
C8—C2—C3—C4	−179.86 (12)	S1—C2—C8—C7	178.78 (11)
S1—C2—C3—C4	0.40 (14)	C6—C7—C8—C2	0.3 (2)
C5—C3—C4—C4ⁱ	179.08 (15)	C9—C7—C8—C2	178.53 (12)
C2—C3—C4—C4ⁱ	0.0 (2)	C8—C7—C9—C10	−80.22 (18)
C5—C3—C4—S1ⁱ	−1.5 (2)	C6—C7—C9—C10	98.04 (17)
C2—C3—C4—S1ⁱ	179.44 (11)	C7—C9—C10—C11	−176.10 (14)
C2—C3—C5—C6	−0.3 (2)	C9—C10—C11—C12	−174.99 (14)
C4—C3—C5—C6	−179.31 (14)	C10—C11—C12—O13	−179.97 (13)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.82	2.02	2.8037 (9)	159
C6—H6···S1ⁱⁱⁱ	0.94	3.36	4.1516 (16)	143
C9—H9A···S1ⁱⁱⁱ	0.98	3.51	4.1374 (19)	124
C10—H10A···S1ⁱⁱⁱ	0.98	3.36	3.9788 (18)	123
C10—H10A···S1^iv	0.98	3.19	3.8825 (16)	129
C11—H11B···S1ⁱⁱⁱ	0.98	3.46	4.1443 (18)	129
C12—H12A···S1^iv	0.98	3.09	3.8488 (17)	135

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A260) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.343 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.664 (4) Å	Cell parameters from 6937 reflections
b = 5.075 (1) Å	θ = 2.4–25.7°
c = 14.419 (4) Å	µ = 0.28 mm⁻¹
β = 108.02 (3)°	T = 260 K
V = 950.8 (4) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.026
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.5°
8501 measured reflections	h = −19→19
2820 independent reflections	k = −6→7
2523 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0729P)² + 0.2289P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.007
2820 reflections	Δρ_max = 0.61 e Å⁻³
121 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.039 (6)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64544 (2)	0.32385 (8)	0.53848 (2)	0.04517 (14)
C2	0.64781 (10)	0.5539 (3)	0.62946 (9)	0.0384 (3)
C3	0.55387 (10)	0.6892 (3)	0.61214 (9)	0.0374 (3)
C4	0.48133 (10)	0.5963 (3)	0.52310 (9)	0.0377 (3)
C5	0.54504 (11)	0.8824 (3)	0.67779 (10)	0.0452 (3)
H5	0.483776	0.974635	0.667425	0.054*
C6	0.62873 (12)	0.9348 (3)	0.75854 (10)	0.0464 (3)
H6	0.622886	1.064072	0.802231	0.056*
C7	0.72226 (11)	0.7991 (3)	0.77666 (9)	0.0427 (3)
C8	0.73161 (11)	0.6065 (3)	0.71170 (10)	0.0437 (3)
H8	0.792851	0.513668	0.722778	0.052*
C9	0.81021 (12)	0.8574 (3)	0.86774 (10)	0.0476 (3)
H9A	0.801509	1.033087	0.890517	0.057*
H9B	0.874279	0.854711	0.852011	0.057*
C10	0.81694 (13)	0.6614 (3)	0.94873 (10)	0.0486 (3)
H10A	0.751029	0.655324	0.960919	0.058*
H10B	0.830091	0.487744	0.927140	0.058*
C11	0.90046 (12)	0.7258 (3)	1.04389 (10)	0.0450 (3)
H11A	0.965695	0.746709	1.031157	0.054*
H11B	0.884152	0.891680	1.069140	0.054*
C12	0.91075 (13)	0.5150 (3)	1.11909 (10)	0.0490 (3)
H12A	0.845777	0.493960	1.132332	0.059*
H12B	0.927451	0.348877	1.094332	0.059*
O13	0.98905 (10)	0.5811 (2)	1.20671 (8)	0.0556 (3)
H13	0.9972 (14)	0.459 (5)	1.2452 (14)	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0386 (2)	0.0539 (2)	0.0393 (2)	0.00628 (13)	0.00669 (13)	−0.00964 (13)
C2	0.0397 (6)	0.0425 (6)	0.0320 (5)	−0.0010 (5)	0.0097 (4)	−0.0016 (5)
C3	0.0393 (6)	0.0410 (6)	0.0316 (5)	−0.0029 (5)	0.0107 (4)	−0.0018 (4)
C4	0.0363 (5)	0.0433 (6)	0.0324 (5)	0.0000 (5)	0.0091 (4)	−0.0021 (5)
C5	0.0461 (7)	0.0490 (7)	0.0390 (6)	0.0015 (6)	0.0108 (5)	−0.0076 (5)
C6	0.0528 (8)	0.0481 (7)	0.0363 (6)	−0.0052 (6)	0.0111 (5)	−0.0086 (5)
C7	0.0468 (7)	0.0462 (7)	0.0314 (6)	−0.0100 (5)	0.0067 (5)	0.0001 (5)
C8	0.0401 (6)	0.0502 (7)	0.0374 (6)	−0.0017 (5)	0.0070 (5)	−0.0015 (5)
C9	0.0519 (8)	0.0485 (7)	0.0352 (6)	−0.0133 (6)	0.0029 (5)	−0.0015 (5)
C10	0.0587 (8)	0.0405 (7)	0.0364 (6)	−0.0102 (6)	−0.0003 (6)	−0.0016 (5)
C11	0.0524 (7)	0.0392 (6)	0.0354 (6)	−0.0068 (5)	0.0017 (5)	−0.0035 (5)
C12	0.0583 (8)	0.0411 (7)	0.0369 (6)	−0.0051 (6)	−0.0007 (5)	−0.0009 (5)
O13	0.0645 (7)	0.0498 (6)	0.0377 (5)	−0.0028 (5)	−0.0057 (5)	0.0002 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7324 (14)	C9—C10	1.515 (2)
S1—C2	1.7489 (13)	C9—H9A	0.9700
C2—C8	1.3959 (18)	C9—H9B	0.9700
C2—C3	1.4082 (18)	C10—C11	1.5241 (19)
C3—C5	1.3939 (18)	C10—H10A	0.9700
C3—C4	1.4371 (17)	C10—H10B	0.9700
C4—C4ⁱ	1.368 (3)	C11—C12	1.499 (2)
C5—C6	1.3820 (19)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C6—C7	1.403 (2)	C12—O13	1.4201 (17)
C6—H6	0.9300	C12—H12A	0.9700
C7—C8	1.387 (2)	C12—H12B	0.9700
C7—C9	1.5100 (19)	O13—H13	0.82 (3)
C8—H8	0.9300

C4ⁱ—S1—C2	90.68 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.37 (12)	C7—C9—H9B	109.1
C8—C2—S1	125.79 (11)	C10—C9—H9B	109.1
C3—C2—S1	112.84 (9)	H9A—C9—H9B	107.8
C5—C3—C2	119.22 (12)	C11—C10—C9	113.78 (12)
C5—C3—C4	131.05 (12)	C11—C10—H10A	108.8
C2—C3—C4	109.72 (11)	C9—C10—H10A	108.8
C4ⁱ—C4—C3	114.29 (14)	C11—C10—H10B	108.8
C4ⁱ—C4—S1ⁱ	112.46 (13)	C9—C10—H10B	108.8
C3—C4—S1ⁱ	133.25 (10)	H10A—C10—H10B	107.7
C6—C5—C3	118.99 (14)	C12—C11—C10	112.02 (12)
C6—C5—H5	120.5	C12—C11—H11A	109.2
C3—C5—H5	120.5	C10—C11—H11A	109.2
C5—C6—C7	122.06 (13)	C12—C11—H11B	109.2
C5—C6—H6	119.0	C10—C11—H11B	109.2
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.28 (13)	O13—C12—C11	110.57 (12)
C8—C7—C9	120.72 (14)	O13—C12—H12A	109.5
C6—C7—C9	119.97 (13)	C11—C12—H12A	109.5
C2—C8—C7	119.06 (13)	O13—C12—H12B	109.5
C2—C8—H8	120.5	C11—C12—H12B	109.5
C7—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.57 (12)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.69 (13)	C3—C5—C6—C7	−0.2 (2)
C4ⁱ—S1—C2—C3	−0.50 (11)	C5—C6—C7—C8	0.1 (2)
C8—C2—C3—C5	1.0 (2)	C5—C6—C7—C9	−177.94 (13)
S1—C2—C3—C5	−178.82 (11)	C3—C2—C8—C7	−1.0 (2)
C8—C2—C3—C4	−179.85 (12)	S1—C2—C8—C7	178.76 (11)
S1—C2—C3—C4	0.33 (14)	C6—C7—C8—C2	0.5 (2)
C5—C3—C4—C4ⁱ	179.10 (16)	C9—C7—C8—C2	178.52 (13)
C2—C3—C4—C4ⁱ	0.1 (2)	C8—C7—C9—C10	−80.25 (19)
C5—C3—C4—S1ⁱ	−1.5 (2)	C6—C7—C9—C10	97.81 (18)
C2—C3—C4—S1ⁱ	179.49 (11)	C7—C9—C10—C11	−176.09 (14)
C2—C3—C5—C6	−0.4 (2)	C9—C10—C11—C12	−174.93 (15)
C4—C3—C5—C6	−179.32 (14)	C10—C11—C12—O13	−179.98 (14)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.82	2.03	2.8028 (9)	158
C6—H6···S1ⁱⁱⁱ	0.93	3.37	4.1564 (17)	143
C9—H9A···S1ⁱⁱⁱ	0.97	3.53	4.144 (2)	124
C10—H10A···S1ⁱⁱⁱ	0.97	3.36	3.9832 (19)	124
C10—H10A···S1^iv	0.97	3.20	3.8870 (17)	129
C11—H11B···S1ⁱⁱⁱ	0.97	3.47	4.1477 (19)	129
C12—H12A···S1^iv	0.97	3.10	3.8528 (19)	135

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A270) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.684 (4) Å	Cell parameters from 7068 reflections
b = 5.074 (1) Å	θ = 2.3–24.8°
c = 14.433 (4) Å	µ = 0.28 mm⁻¹
β = 108.11 (3)°	T = 270 K
V = 952.5 (4) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.028
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.5°
8556 measured reflections	h = −19→19
2820 independent reflections	k = −6→7
2505 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.0721P)² + 0.223P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.027
2820 reflections	Δρ_max = 0.58 e Å⁻³
121 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.037 (5)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64527 (3)	0.32388 (8)	0.53853 (2)	0.04703 (14)
C2	0.64764 (10)	0.5535 (3)	0.62945 (9)	0.0400 (3)
C3	0.55373 (10)	0.6890 (3)	0.61207 (9)	0.0391 (3)
C4	0.48127 (10)	0.5962 (3)	0.52312 (9)	0.0391 (3)
C5	0.54510 (12)	0.8820 (3)	0.67776 (10)	0.0472 (3)
H5	0.483932	0.974372	0.667356	0.057*
C6	0.62871 (12)	0.9341 (3)	0.75862 (10)	0.0485 (3)
H6	0.622860	1.063060	0.802394	0.058*
C7	0.72218 (11)	0.7984 (3)	0.77668 (9)	0.0446 (3)
C8	0.73146 (11)	0.6066 (3)	0.71186 (10)	0.0454 (3)
H8	0.792702	0.514089	0.722947	0.054*
C9	0.81006 (13)	0.8567 (3)	0.86778 (10)	0.0499 (3)
H9A	0.801434	1.032486	0.890469	0.060*
H9B	0.874053	0.853790	0.852130	0.060*
C10	0.81686 (14)	0.6613 (3)	0.94871 (11)	0.0507 (4)
H10A	0.751042	0.655458	0.960845	0.061*
H10B	0.829900	0.487484	0.927189	0.061*
C11	0.90039 (12)	0.7255 (3)	1.04391 (10)	0.0468 (3)
H11A	0.965557	0.746026	1.031251	0.056*
H11B	0.884223	0.891586	1.069074	0.056*
C12	0.91063 (13)	0.5154 (3)	1.11903 (10)	0.0511 (3)
H12A	0.845732	0.494723	1.132215	0.061*
H12B	0.927211	0.349064	1.094381	0.061*
O13	0.98896 (10)	0.5816 (2)	1.20666 (8)	0.0582 (3)
H13	0.9969 (14)	0.462 (5)	1.2444 (14)	0.087*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0402 (2)	0.0562 (2)	0.0407 (2)	0.00652 (13)	0.00694 (14)	−0.00996 (13)
C2	0.0410 (6)	0.0448 (7)	0.0333 (5)	−0.0012 (5)	0.0102 (4)	−0.0018 (5)
C3	0.0417 (6)	0.0427 (6)	0.0328 (5)	−0.0029 (5)	0.0116 (5)	−0.0019 (4)
C4	0.0378 (5)	0.0448 (6)	0.0336 (5)	0.0004 (5)	0.0094 (4)	−0.0021 (5)
C5	0.0482 (7)	0.0515 (7)	0.0404 (6)	0.0014 (6)	0.0115 (6)	−0.0078 (6)
C6	0.0554 (8)	0.0508 (8)	0.0370 (6)	−0.0052 (6)	0.0111 (6)	−0.0092 (5)
C7	0.0491 (7)	0.0483 (7)	0.0324 (6)	−0.0109 (5)	0.0068 (5)	0.0001 (5)
C8	0.0415 (6)	0.0522 (8)	0.0385 (6)	−0.0021 (5)	0.0068 (5)	−0.0020 (5)
C9	0.0542 (8)	0.0509 (8)	0.0368 (6)	−0.0135 (6)	0.0030 (6)	−0.0017 (5)
C10	0.0614 (9)	0.0427 (7)	0.0374 (6)	−0.0111 (6)	−0.0003 (6)	−0.0019 (5)
C11	0.0546 (7)	0.0408 (7)	0.0367 (6)	−0.0065 (6)	0.0023 (5)	−0.0034 (5)
C12	0.0607 (8)	0.0436 (7)	0.0380 (6)	−0.0054 (6)	−0.0008 (6)	−0.0019 (5)
O13	0.0673 (7)	0.0522 (6)	0.0396 (5)	−0.0036 (5)	−0.0061 (5)	0.0000 (4)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7311 (14)	C9—C10	1.513 (2)
S1—C2	1.7477 (14)	C9—H9A	0.9700
C2—C8	1.3980 (18)	C9—H9B	0.9700
C2—C3	1.4094 (19)	C10—C11	1.524 (2)
C3—C5	1.3931 (18)	C10—H10A	0.9700
C3—C4	1.4359 (17)	C10—H10B	0.9700
C4—C4ⁱ	1.369 (3)	C11—C12	1.496 (2)
C5—C6	1.382 (2)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C6—C7	1.404 (2)	C12—O13	1.4207 (17)
C6—H6	0.9300	C12—H12A	0.9700
C7—C8	1.383 (2)	C12—H12B	0.9700
C7—C9	1.5097 (19)	O13—H13	0.80 (3)
C8—H8	0.9300

C4ⁱ—S1—C2	90.68 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.26 (13)	C7—C9—H9B	109.1
C8—C2—S1	125.88 (11)	C10—C9—H9B	109.1
C3—C2—S1	112.86 (10)	H9A—C9—H9B	107.8
C5—C3—C2	119.15 (12)	C11—C10—C9	113.89 (12)
C5—C3—C4	131.14 (13)	C11—C10—H10A	108.8
C2—C3—C4	109.70 (11)	C9—C10—H10A	108.8
C4ⁱ—C4—C3	114.25 (15)	C11—C10—H10B	108.8
C4ⁱ—C4—S1ⁱ	112.51 (13)	C9—C10—H10B	108.8
C3—C4—S1ⁱ	133.24 (10)	H10A—C10—H10B	107.7
C6—C5—C3	119.08 (14)	C12—C11—C10	112.10 (12)
C6—C5—H5	120.5	C12—C11—H11A	109.2
C3—C5—H5	120.5	C10—C11—H11A	109.2
C5—C6—C7	122.00 (13)	C12—C11—H11B	109.2
C5—C6—H6	119.0	C10—C11—H11B	109.2
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.31 (13)	O13—C12—C11	110.59 (12)
C8—C7—C9	120.74 (14)	O13—C12—H12A	109.5
C6—C7—C9	119.91 (14)	C11—C12—H12A	109.5
C2—C8—C7	119.18 (13)	O13—C12—H12B	109.5
C2—C8—H8	120.4	C11—C12—H12B	109.5
C7—C8—H8	120.4	H12A—C12—H12B	108.1
C7—C9—C10	112.67 (12)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.82 (13)	C3—C5—C6—C7	0.0 (2)
C4ⁱ—S1—C2—C3	−0.48 (11)	C5—C6—C7—C8	0.1 (2)
C8—C2—C3—C5	0.9 (2)	C5—C6—C7—C9	−178.01 (14)
S1—C2—C3—C5	−178.80 (11)	C3—C2—C8—C7	−0.9 (2)
C8—C2—C3—C4	−179.86 (13)	S1—C2—C8—C7	178.77 (11)
S1—C2—C3—C4	0.42 (14)	C6—C7—C8—C2	0.4 (2)
C5—C3—C4—C4ⁱ	178.99 (16)	C9—C7—C8—C2	178.46 (13)
C2—C3—C4—C4ⁱ	−0.1 (2)	C8—C7—C9—C10	−80.40 (19)
C5—C3—C4—S1ⁱ	−1.3 (2)	C6—C7—C9—C10	97.64 (18)
C2—C3—C4—S1ⁱ	179.57 (11)	C7—C9—C10—C11	−176.12 (15)
C2—C3—C5—C6	−0.4 (2)	C9—C10—C11—C12	−174.96 (15)
C4—C3—C5—C6	−179.46 (14)	C10—C11—C12—O13	−179.97 (14)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.80	2.05	2.8032 (10)	158
C6—H6···S1ⁱⁱⁱ	0.93	3.37	4.1606 (18)	144
C9—H9A···S1ⁱⁱⁱ	0.97	3.54	4.152 (2)	124
C10—H10A···S1ⁱⁱⁱ	0.97	3.37	3.989 (2)	124
C10—H10A···S1^iv	0.97	3.21	3.8920 (18)	129
C11—H11B···S1ⁱⁱⁱ	0.97	3.47	4.1536 (19)	129
C12—H12A···S1^iv	0.97	3.11	3.8570 (19)	135

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A280) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.338 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.705 (3) Å	Cell parameters from 6934 reflections
b = 5.074 (1) Å	θ = 2.3–25.8°
c = 14.447 (3) Å	µ = 0.28 mm⁻¹
β = 108.20 (2)°	T = 280 K
V = 954.4 (3) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.024
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.5°
8550 measured reflections	h = −19→19
2833 independent reflections	k = −6→7
2496 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.075P)² + 0.230P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.023
2833 reflections	Δρ_max = 0.56 e Å⁻³
121 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.041 (5)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64509 (3)	0.32388 (8)	0.53858 (3)	0.04930 (15)
C2	0.64762 (10)	0.5535 (3)	0.62956 (9)	0.0418 (3)
C3	0.55374 (10)	0.6887 (3)	0.61223 (9)	0.0410 (3)
C4	0.48133 (10)	0.5962 (3)	0.52311 (9)	0.0409 (3)
C5	0.54511 (12)	0.8814 (3)	0.67781 (11)	0.0494 (3)
H5	0.483993	0.973760	0.667355	0.059*
C6	0.62866 (12)	0.9336 (3)	0.75869 (10)	0.0508 (3)
H6	0.622841	1.062307	0.802482	0.061*
C7	0.72204 (12)	0.7980 (3)	0.77669 (10)	0.0466 (3)
C8	0.73134 (11)	0.6061 (3)	0.71192 (10)	0.0475 (3)
H8	0.792497	0.513513	0.723063	0.057*
C9	0.81003 (13)	0.8562 (3)	0.86786 (11)	0.0522 (4)
H9A	0.801544	1.032180	0.890453	0.063*
H9B	0.873910	0.852914	0.852252	0.063*
C10	0.81682 (14)	0.6614 (3)	0.94879 (11)	0.0530 (4)
H10A	0.751071	0.655811	0.960820	0.064*
H10B	0.829754	0.487413	0.927359	0.064*
C11	0.90021 (13)	0.7253 (3)	1.04398 (10)	0.0492 (3)
H11A	0.965304	0.745653	1.031400	0.059*
H11B	0.884118	0.891468	1.069049	0.059*
C12	0.91053 (13)	0.5158 (3)	1.11912 (11)	0.0540 (4)
H12A	0.845726	0.495255	1.132243	0.065*
H12B	0.927039	0.349301	1.094568	0.065*
O13	0.98872 (10)	0.5817 (3)	1.20666 (8)	0.0612 (3)
H13	0.9968 (14)	0.461 (5)	1.2446 (14)	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0422 (2)	0.0588 (3)	0.0427 (2)	0.00682 (13)	0.00721 (14)	−0.01032 (14)
C2	0.0427 (6)	0.0465 (7)	0.0350 (5)	−0.0011 (5)	0.0105 (5)	−0.0016 (5)
C3	0.0432 (6)	0.0449 (7)	0.0345 (6)	−0.0026 (5)	0.0118 (5)	−0.0017 (5)
C4	0.0396 (6)	0.0472 (7)	0.0348 (5)	0.0002 (5)	0.0099 (4)	−0.0017 (5)
C5	0.0505 (7)	0.0539 (8)	0.0422 (7)	0.0014 (6)	0.0120 (6)	−0.0083 (6)
C6	0.0581 (8)	0.0533 (8)	0.0386 (6)	−0.0055 (6)	0.0116 (6)	−0.0095 (6)
C7	0.0514 (7)	0.0501 (7)	0.0338 (6)	−0.0112 (6)	0.0069 (5)	0.0000 (5)
C8	0.0434 (7)	0.0545 (8)	0.0406 (6)	−0.0021 (6)	0.0072 (5)	−0.0019 (6)
C9	0.0563 (8)	0.0535 (8)	0.0383 (6)	−0.0140 (6)	0.0024 (6)	−0.0017 (6)
C10	0.0633 (9)	0.0448 (7)	0.0395 (7)	−0.0110 (6)	−0.0004 (6)	−0.0022 (5)
C11	0.0571 (8)	0.0432 (7)	0.0383 (6)	−0.0076 (6)	0.0020 (6)	−0.0041 (5)
C12	0.0640 (9)	0.0452 (7)	0.0407 (7)	−0.0053 (6)	−0.0012 (6)	−0.0020 (6)
O13	0.0707 (8)	0.0547 (6)	0.0413 (5)	−0.0037 (5)	−0.0067 (5)	0.0000 (5)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7309 (14)	C9—C10	1.512 (2)
S1—C2	1.7485 (14)	C9—H9A	0.9700
C2—C8	1.3966 (19)	C9—H9B	0.9700
C2—C3	1.4099 (19)	C10—C11	1.523 (2)
C3—C5	1.3919 (19)	C10—H10A	0.9700
C3—C4	1.4370 (18)	C10—H10B	0.9700
C4—C4ⁱ	1.369 (3)	C11—C12	1.494 (2)
C5—C6	1.382 (2)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C6—C7	1.404 (2)	C12—O13	1.4187 (17)
C6—H6	0.9300	C12—H12A	0.9700
C7—C8	1.383 (2)	C12—H12B	0.9700
C7—C9	1.5112 (19)	O13—H13	0.81 (3)
C8—H8	0.9300

C4ⁱ—S1—C2	90.72 (7)	C10—C9—H9A	109.1
C8—C2—C3	121.29 (13)	C7—C9—H9B	109.1
C8—C2—S1	125.87 (11)	C10—C9—H9B	109.1
C3—C2—S1	112.83 (10)	H9A—C9—H9B	107.8
C5—C3—C2	119.20 (12)	C11—C10—C9	114.00 (12)
C5—C3—C4	131.12 (13)	C11—C10—H10A	108.8
C2—C3—C4	109.66 (12)	C9—C10—H10A	108.8
C4ⁱ—C4—C3	114.29 (15)	C11—C10—H10B	108.8
C4ⁱ—C4—S1ⁱ	112.49 (13)	C9—C10—H10B	108.8
C3—C4—S1ⁱ	133.22 (11)	H10A—C10—H10B	107.6
C6—C5—C3	119.06 (14)	C12—C11—C10	112.25 (12)
C6—C5—H5	120.5	C12—C11—H11A	109.2
C3—C5—H5	120.5	C10—C11—H11A	109.2
C5—C6—C7	121.96 (14)	C12—C11—H11B	109.2
C5—C6—H6	119.0	C10—C11—H11B	109.2
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.39 (13)	O13—C12—C11	110.71 (13)
C8—C7—C9	120.67 (15)	O13—C12—H12A	109.5
C6—C7—C9	119.91 (14)	C11—C12—H12A	109.5
C2—C8—C7	119.08 (14)	O13—C12—H12B	109.5
C2—C8—H8	120.5	C11—C12—H12B	109.5
C7—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.69 (12)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.76 (14)	C3—C5—C6—C7	0.0 (2)
C4ⁱ—S1—C2—C3	−0.39 (11)	C5—C6—C7—C8	0.0 (2)
C8—C2—C3—C5	1.1 (2)	C5—C6—C7—C9	−178.05 (14)
S1—C2—C3—C5	−178.80 (11)	C3—C2—C8—C7	−1.1 (2)
C8—C2—C3—C4	−179.90 (13)	S1—C2—C8—C7	178.78 (11)
S1—C2—C3—C4	0.25 (15)	C6—C7—C8—C2	0.5 (2)
C5—C3—C4—C4ⁱ	178.97 (16)	C9—C7—C8—C2	178.55 (13)
C2—C3—C4—C4ⁱ	0.1 (2)	C8—C7—C9—C10	−80.6 (2)
C5—C3—C4—S1ⁱ	−1.5 (3)	C6—C7—C9—C10	97.46 (18)
C2—C3—C4—S1ⁱ	179.60 (11)	C7—C9—C10—C11	−176.07 (15)
C2—C3—C5—C6	−0.5 (2)	C9—C10—C11—C12	−174.92 (16)
C4—C3—C5—C6	−179.33 (14)	C10—C11—C12—O13	−179.98 (15)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.81	2.04	2.8033 (10)	158
C6—H6···S1ⁱⁱⁱ	0.93	3.38	4.1651 (16)	144
C9—H9A···S1ⁱⁱⁱ	0.97	3.55	4.161 (2)	124
C10—H10A···S1ⁱⁱⁱ	0.97	3.37	3.994 (2)	124
C10—H10A···S1^iv	0.97	3.21	3.8978 (18)	129
C11—H11B···S1ⁱⁱⁱ	0.97	3.48	4.1586 (19)	129
C12—H12A···S1^iv	0.97	3.11	3.8619 (19)	135

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A290) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.336 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.725 (2) Å	Cell parameters from 7019 reflections
b = 5.073 (1) Å	θ = 2.2–24.9°
c = 14.461 (2) Å	µ = 0.28 mm⁻¹
β = 108.301 (19)°	T = 290 K
V = 955.9 (2) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.026
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.5°
8549 measured reflections	h = −19→19
2837 independent reflections	k = −6→7
2459 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.131	w = 1/[σ²(F_o²) + (0.0738P)² + 0.2136P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.020
2837 reflections	Δρ_max = 0.57 e Å⁻³
121 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.038 (5)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64493 (3)	0.32387 (8)	0.53867 (3)	0.05145 (15)
C2	0.64750 (10)	0.5533 (3)	0.62957 (9)	0.0435 (3)
C3	0.55371 (10)	0.6887 (3)	0.61224 (9)	0.0425 (3)
C4	0.48135 (10)	0.5960 (3)	0.52307 (9)	0.0426 (3)
C5	0.54518 (12)	0.8809 (3)	0.67780 (11)	0.0513 (3)
H5	0.484116	0.973137	0.667379	0.062*
C6	0.62864 (12)	0.9328 (3)	0.75863 (10)	0.0530 (3)
H6	0.622847	1.061523	0.802391	0.064*
C7	0.72190 (12)	0.7974 (3)	0.77677 (10)	0.0486 (3)
C8	0.73118 (11)	0.6058 (3)	0.71199 (10)	0.0494 (3)
H8	0.792290	0.513319	0.723158	0.059*
C9	0.80976 (13)	0.8560 (3)	0.86797 (11)	0.0544 (4)
H9A	0.801187	1.031930	0.890519	0.065*
H9B	0.873588	0.852910	0.852498	0.065*
C10	0.81663 (14)	0.6613 (3)	0.94876 (11)	0.0553 (4)
H10A	0.750973	0.655757	0.960749	0.066*
H10B	0.829480	0.487280	0.927323	0.066*
C11	0.90008 (13)	0.7250 (3)	1.04400 (10)	0.0513 (3)
H11A	0.965088	0.745096	1.031468	0.062*
H11B	0.884126	0.891420	1.068996	0.062*
C12	0.91040 (14)	0.5163 (3)	1.11904 (11)	0.0565 (4)
H12A	0.845674	0.496019	1.132114	0.068*
H12B	0.926783	0.349583	1.094572	0.068*
O13	0.98862 (10)	0.5822 (3)	1.20658 (8)	0.0641 (3)
H13	0.9951 (14)	0.466 (5)	1.2447 (14)	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0439 (2)	0.0612 (3)	0.0448 (2)	0.00709 (14)	0.00761 (14)	−0.01063 (14)
C2	0.0450 (6)	0.0480 (7)	0.0361 (5)	−0.0018 (5)	0.0108 (5)	−0.0015 (5)
C3	0.0448 (6)	0.0461 (7)	0.0361 (6)	−0.0029 (5)	0.0123 (5)	−0.0019 (5)
C4	0.0417 (6)	0.0487 (7)	0.0364 (5)	0.0001 (5)	0.0107 (5)	−0.0019 (5)
C5	0.0522 (7)	0.0554 (8)	0.0441 (7)	0.0016 (6)	0.0119 (6)	−0.0086 (6)
C6	0.0603 (8)	0.0557 (8)	0.0405 (6)	−0.0056 (6)	0.0120 (6)	−0.0098 (6)
C7	0.0535 (7)	0.0528 (8)	0.0350 (6)	−0.0117 (6)	0.0072 (5)	−0.0001 (5)
C8	0.0460 (7)	0.0560 (8)	0.0420 (6)	−0.0023 (6)	0.0075 (5)	−0.0016 (6)
C9	0.0587 (8)	0.0559 (8)	0.0402 (6)	−0.0146 (6)	0.0035 (6)	−0.0016 (6)
C10	0.0657 (9)	0.0468 (7)	0.0413 (7)	−0.0114 (6)	−0.0005 (6)	−0.0022 (6)
C11	0.0591 (8)	0.0455 (7)	0.0399 (6)	−0.0075 (6)	0.0021 (6)	−0.0039 (5)
C12	0.0673 (9)	0.0472 (7)	0.0423 (7)	−0.0058 (6)	−0.0010 (6)	−0.0016 (6)
O13	0.0740 (8)	0.0569 (7)	0.0437 (6)	−0.0035 (6)	−0.0067 (5)	0.0000 (5)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7305 (14)	C9—C10	1.510 (2)
S1—C2	1.7476 (14)	C9—H9A	0.9700
C2—C8	1.3969 (18)	C9—H9B	0.9700
C2—C3	1.4105 (19)	C10—C11	1.524 (2)
C3—C5	1.3901 (19)	C10—H10A	0.9700
C3—C4	1.4373 (18)	C10—H10B	0.9700
C4—C4ⁱ	1.368 (3)	C11—C12	1.491 (2)
C5—C6	1.381 (2)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C6—C7	1.403 (2)	C12—O13	1.4190 (17)
C6—H6	0.9300	C12—H12A	0.9700
C7—C8	1.383 (2)	C12—H12B	0.9700
C7—C9	1.5110 (19)	O13—H13	0.79 (3)
C8—H8	0.9300

C4ⁱ—S1—C2	90.69 (6)	C10—C9—H9A	109.1
C8—C2—C3	121.24 (13)	C7—C9—H9B	109.1
C8—C2—S1	125.87 (11)	C10—C9—H9B	109.1
C3—C2—S1	112.90 (10)	H9A—C9—H9B	107.8
C5—C3—C2	119.21 (12)	C11—C10—C9	114.02 (13)
C5—C3—C4	131.22 (13)	C11—C10—H10A	108.7
C2—C3—C4	109.57 (12)	C9—C10—H10A	108.7
C4ⁱ—C4—C3	114.31 (15)	C11—C10—H10B	108.7
C4ⁱ—C4—S1ⁱ	112.53 (13)	C9—C10—H10B	108.7
C3—C4—S1ⁱ	133.15 (11)	H10A—C10—H10B	107.6
C6—C5—C3	119.07 (14)	C12—C11—C10	112.32 (13)
C6—C5—H5	120.5	C12—C11—H11A	109.1
C3—C5—H5	120.5	C10—C11—H11A	109.1
C5—C6—C7	122.05 (14)	C12—C11—H11B	109.1
C5—C6—H6	119.0	C10—C11—H11B	109.1
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.33 (13)	O13—C12—C11	110.75 (13)
C8—C7—C9	120.75 (15)	O13—C12—H12A	109.5
C6—C7—C9	119.88 (14)	C11—C12—H12A	109.5
C2—C8—C7	119.09 (14)	O13—C12—H12B	109.5
C2—C8—H8	120.5	C11—C12—H12B	109.5
C7—C8—H8	120.5	H12A—C12—H12B	108.1
C7—C9—C10	112.68 (12)	C12—O13—H13	109.5
C7—C9—H9A	109.1

C4ⁱ—S1—C2—C8	179.76 (14)	C3—C5—C6—C7	−0.1 (2)
C4ⁱ—S1—C2—C3	−0.38 (11)	C5—C6—C7—C8	0.1 (2)
C8—C2—C3—C5	1.0 (2)	C5—C6—C7—C9	−178.08 (14)
S1—C2—C3—C5	−178.86 (11)	C3—C2—C8—C7	−1.0 (2)
C8—C2—C3—C4	−179.87 (13)	S1—C2—C8—C7	178.84 (11)
S1—C2—C3—C4	0.27 (15)	C6—C7—C8—C2	0.5 (2)
C5—C3—C4—C4ⁱ	179.02 (16)	C9—C7—C8—C2	178.60 (14)
C2—C3—C4—C4ⁱ	0.0 (2)	C8—C7—C9—C10	−80.6 (2)
C5—C3—C4—S1ⁱ	−1.4 (3)	C6—C7—C9—C10	97.50 (19)
C2—C3—C4—S1ⁱ	179.62 (11)	C7—C9—C10—C11	−176.20 (15)
C2—C3—C5—C6	−0.5 (2)	C9—C10—C11—C12	−175.02 (16)
C4—C3—C5—C6	−179.36 (15)	C10—C11—C12—O13	−179.97 (15)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.79	2.06	2.8039 (10)	157
C6—H6···S1ⁱⁱⁱ	0.93	3.38	4.1720 (15)	144
C9—H9A···S1ⁱⁱⁱ	0.97	3.55	4.166 (2)	124
C10—H10A···S1ⁱⁱⁱ	0.97	3.37	3.999 (2)	124
C10—H10A···S1^iv	0.97	3.22	3.9020 (18)	129
C11—H11B···S1ⁱⁱⁱ	0.97	3.49	4.1637 (18)	129
C12—H12A···S1^iv	0.97	3.12	3.8657 (18)	135

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

(A300) top

Crystal data top

C₂₂H₂₄O₂S₂	F(000) = 408
M_r = 384.53	D_x = 1.333 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.700 Å
a = 13.748 (6) Å	Cell parameters from 7097 reflections
b = 5.072 (1) Å	θ = 2.2–26.0°
c = 14.477 (2) Å	µ = 0.28 mm⁻¹
β = 108.402 (19)°	T = 300 K
V = 957.9 (5) Å³	Prism, colourless
Z = 2	0.12 × 0.06 × 0.02 mm

Data collection top

Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer	R_int = 0.029
Rotating crystal scans	θ_max = 29.9°, θ_min = 1.5°
8661 measured reflections	h = −19→19
2848 independent reflections	k = −6→7
2430 reflections with I > 2σ(I)	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0542P)² + 0.4979P] where P = (F_o² + 2F_c²)/3
S = 0.87	(Δ/σ)_max = 0.002
2848 reflections	Δρ_max = 0.55 e Å⁻³
121 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: iterative	Extinction coefficient: 0.041 (4)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.64475 (3)	0.32392 (9)	0.53874 (3)	0.05383 (15)
C2	0.64721 (11)	0.5528 (3)	0.62963 (10)	0.0456 (3)
C3	0.55382 (11)	0.6883 (3)	0.61223 (10)	0.0442 (3)
C4	0.48133 (11)	0.5959 (3)	0.52300 (10)	0.0444 (3)
C5	0.54530 (13)	0.8803 (3)	0.67786 (11)	0.0536 (4)
H5	0.484299	0.972510	0.667429	0.064*
C6	0.62870 (13)	0.9321 (4)	0.75869 (11)	0.0554 (4)
H6	0.622949	1.060750	0.802436	0.066*
C7	0.72192 (12)	0.7966 (3)	0.77694 (10)	0.0507 (3)
C8	0.73081 (12)	0.6058 (4)	0.71227 (11)	0.0517 (3)
H8	0.791831	0.513193	0.723485	0.062*
C9	0.80957 (14)	0.8555 (4)	0.86810 (11)	0.0570 (4)
H9A	0.800908	1.031508	0.890522	0.068*
H9B	0.873323	0.852622	0.852740	0.068*
C10	0.81662 (15)	0.6613 (3)	0.94886 (11)	0.0577 (4)
H10A	0.751038	0.655556	0.960716	0.069*
H10B	0.829526	0.487236	0.927515	0.069*
C11	0.89981 (14)	0.7250 (3)	1.04406 (11)	0.0538 (4)
H11A	0.964736	0.745490	1.031656	0.065*
H11B	0.883759	0.891276	1.069011	0.065*
C12	0.91033 (14)	0.5164 (3)	1.11899 (11)	0.0586 (4)
H12A	0.845703	0.495663	1.131943	0.070*
H12B	0.926876	0.349836	1.094608	0.070*
O13	0.98838 (11)	0.5828 (3)	1.20654 (8)	0.0669 (4)
H13	0.9966 (15)	0.467 (5)	1.2428 (15)	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0455 (2)	0.0642 (3)	0.0470 (2)	0.00729 (16)	0.00796 (15)	−0.01114 (17)
C2	0.0470 (7)	0.0505 (8)	0.0378 (6)	−0.0018 (6)	0.0114 (5)	−0.0012 (6)
C3	0.0463 (7)	0.0486 (8)	0.0375 (6)	−0.0032 (6)	0.0128 (5)	−0.0023 (5)
C4	0.0428 (6)	0.0509 (8)	0.0383 (6)	−0.0005 (6)	0.0111 (5)	−0.0023 (6)
C5	0.0538 (8)	0.0586 (9)	0.0467 (8)	0.0014 (7)	0.0133 (6)	−0.0084 (7)
C6	0.0634 (9)	0.0580 (9)	0.0423 (7)	−0.0063 (7)	0.0132 (6)	−0.0103 (7)
C7	0.0551 (8)	0.0550 (9)	0.0372 (6)	−0.0121 (7)	0.0079 (6)	0.0006 (6)
C8	0.0470 (7)	0.0588 (9)	0.0447 (7)	−0.0026 (6)	0.0081 (6)	−0.0016 (7)
C9	0.0609 (9)	0.0588 (9)	0.0424 (7)	−0.0148 (7)	0.0034 (6)	−0.0025 (7)
C10	0.0681 (10)	0.0492 (8)	0.0434 (7)	−0.0113 (7)	0.0001 (7)	−0.0026 (6)
C11	0.0614 (9)	0.0476 (8)	0.0425 (7)	−0.0079 (7)	0.0024 (6)	−0.0045 (6)
C12	0.0680 (10)	0.0507 (9)	0.0440 (7)	−0.0057 (7)	−0.0010 (7)	−0.0021 (7)
O13	0.0771 (8)	0.0596 (7)	0.0452 (6)	−0.0036 (6)	−0.0074 (6)	−0.0006 (5)

Geometric parameters (Å, º) top

S1—C4ⁱ	1.7294 (16)	C9—C10	1.508 (2)
S1—C2	1.7471 (15)	C9—H9A	0.9700
C2—C8	1.399 (2)	C9—H9B	0.9700
C2—C3	1.407 (2)	C10—C11	1.522 (2)
C3—C5	1.391 (2)	C10—H10A	0.9700
C3—C4	1.4384 (19)	C10—H10B	0.9700
C4—C4ⁱ	1.367 (3)	C11—C12	1.489 (2)
C5—C6	1.381 (2)	C11—H11A	0.9700
C5—H5	0.9300	C11—H11B	0.9700
C6—C7	1.404 (3)	C12—O13	1.4186 (18)
C6—H6	0.9300	C12—H12A	0.9700
C7—C8	1.378 (2)	C12—H12B	0.9700
C7—C9	1.510 (2)	O13—H13	0.77 (3)
C8—H8	0.9300

C4ⁱ—S1—C2	90.62 (7)	C10—C9—H9A	109.0
C8—C2—C3	121.07 (14)	C7—C9—H9B	109.0
C8—C2—S1	125.96 (12)	C10—C9—H9B	109.0
C3—C2—S1	112.96 (10)	H9A—C9—H9B	107.8
C5—C3—C2	119.24 (13)	C11—C10—C9	114.16 (14)
C5—C3—C4	131.13 (14)	C11—C10—H10A	108.7
C2—C3—C4	109.62 (13)	C9—C10—H10A	108.7
C4ⁱ—C4—C3	114.16 (16)	C11—C10—H10B	108.7
C4ⁱ—C4—S1ⁱ	112.63 (14)	C9—C10—H10B	108.7
C3—C4—S1ⁱ	133.21 (12)	H10A—C10—H10B	107.6
C6—C5—C3	119.06 (15)	C12—C11—C10	112.41 (14)
C6—C5—H5	120.5	C12—C11—H11A	109.1
C3—C5—H5	120.5	C10—C11—H11A	109.1
C5—C6—C7	122.07 (15)	C12—C11—H11B	109.1
C5—C6—H6	119.0	C10—C11—H11B	109.1
C7—C6—H6	119.0	H11A—C11—H11B	107.9
C8—C7—C6	119.16 (14)	O13—C12—C11	110.76 (14)
C8—C7—C9	121.02 (16)	O13—C12—H12A	109.5
C6—C7—C9	119.80 (15)	C11—C12—H12A	109.5
C2—C8—C7	119.39 (15)	O13—C12—H12B	109.5
C2—C8—H8	120.3	C11—C12—H12B	109.5
C7—C8—H8	120.3	H12A—C12—H12B	108.1
C7—C9—C10	112.74 (14)	C12—O13—H13	109.5
C7—C9—H9A	109.0

C4ⁱ—S1—C2—C8	179.82 (15)	C3—C5—C6—C7	−0.1 (3)
C4ⁱ—S1—C2—C3	−0.52 (12)	C5—C6—C7—C8	0.0 (3)
C8—C2—C3—C5	0.8 (2)	C5—C6—C7—C9	−178.14 (16)
S1—C2—C3—C5	−178.84 (12)	C3—C2—C8—C7	−0.9 (2)
C8—C2—C3—C4	−179.87 (14)	S1—C2—C8—C7	178.70 (12)
S1—C2—C3—C4	0.45 (16)	C6—C7—C8—C2	0.5 (2)
C5—C3—C4—C4ⁱ	179.07 (18)	C9—C7—C8—C2	178.65 (15)
C2—C3—C4—C4ⁱ	−0.1 (2)	C8—C7—C9—C10	−80.6 (2)
C5—C3—C4—S1ⁱ	−1.3 (3)	C6—C7—C9—C10	97.5 (2)
C2—C3—C4—S1ⁱ	179.53 (12)	C7—C9—C10—C11	−176.21 (16)
C2—C3—C5—C6	−0.3 (2)	C9—C10—C11—C12	−174.94 (17)
C4—C3—C5—C6	−179.41 (16)	C10—C11—C12—O13	−179.94 (16)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13···O13ⁱⁱ	0.77	2.07	2.8041 (11)	159
C6—H6···S1ⁱⁱⁱ	0.93	3.39	4.1776 (17)	144
C9—H9A···S1ⁱⁱⁱ	0.97	3.56	4.173 (2)	124
C10—H10A···S1ⁱⁱⁱ	0.97	3.38	4.004 (2)	124
C10—H10A···S1^iv	0.97	3.22	3.908 (2)	129
C11—H11B···S1ⁱⁱⁱ	0.97	3.49	4.167 (2)	129
C12—H12A···S1^iv	0.97	3.12	3.871 (2)	136

Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2.

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Format		BIBTeX
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A positive to negative uniaxial thermal expansion crossover in an organic benzothienobenzo­thio­phene structure

Supporting information

A positive to negative uniaxial thermal expansion crossover in an organic benzothienobenzothiophene structure