[(1R,3S)-3-(1,3-Dithian-2-yl)-2,2-dimethyl­cyclo­prop­yl]diphenyl­methanol

Na, R.; Wang, M.

doi:10.1107/S1600536809016079

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1230

doi:10.1107/S1600536809016079

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[(1R,3S)-3-(1,3-Dithian-2-yl)-2,2-dimethylcyclopropyl]diphenylmethanol

Risong Na ^a and Min Wang ^a ^*

^aDepartment of Applied Chemistry, China Agricultural University, 100193 Beijing, People's Republic of China
^*Correspondence e-mail: wangmincau@yahoo.com.cn

(Received 30 March 2009; accepted 29 April 2009; online 7 May 2009)

In the title compound, C₂₂H₂₆OS₂, prepared from (–)-1R-cis-caronaldehyde, the 1,3-dithiane ring adopts a chair conformation. An intramolecular O—H⋯S hydrogen bond influences the molecular conformation. In the crystal, weak intermolecular C—H⋯S and C—H⋯O hydrogen bonds link the molecules into chains propagating along [010].

Related literature

For the details of preparation of the analogous compound, (1R,3S)-methyl-3-(1,3-dithian-2-yl)-2,2-dimethylcyclopropane carboxylate, see: Mazzanti et al. (1997 ); Veyrat et al. (1997 ); Perollier et al. (1997 ).

Experimental

Crystal data

C₂₂H₂₆OS₂
M_r = 370.55
Monoclinic, P 2₁
a = 9.5578 (19) Å
b = 11.199 (2) Å
c = 9.6512 (19) Å
β = 101.14 (3)°
V = 1013.6 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 123 K
0.40 × 0.40 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.900, T_max = 0.924
4303 measured reflections
4303 independent reflections
2920 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.084
S = 0.84
4303 reflections
229 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: Flack (1983 ), 1878 Friedel pairs
Flack parameter: 0.05 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H2⋯S1	0.84	2.58	3.330 (2)	149
C7—H7A⋯S2ⁱ	0.99	2.89	3.736 (3)	144
C9—H9A⋯O1ⁱⁱ	0.99	2.60	3.236 (3)	122
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

Data collection: RAPID-AUTO (Rigaku, 2000 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016079/cv2542sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016079/cv2542Isup2.hkl

checkCIF report

Comment top

We designed and prepared a novel type of chiral dithiane alcohol based with chiral cis-cyclopropane from (-)-1R-cis-Caronaldehyde. Details of preparation of the analogue compound were descussed in the literature (Mazzanti et al., 1997; Veyrat et al., 1997; Perollier et al., 1997).

In this paper, the crystal structure of the title compound, (I), is reported. In (I) (Fig. 1), the 1,3-dithiane ring adopts a chair conformation. Intramolecular O—H···S hydrogen bond (Table 1) influences the molecular conformation. In the crystal, weak intermolecular C—H···O and C—H···S hydrogen bonds (Table 1) link the molecules into chains propagated in direction [010].

Related literature top

For the details of preparation of the analogous compound, (1R,3S)-methyl-3-(1,3-dithian-2-yl)-2,2-dimethylcyclopropane carboxylate, see: Mazzanti et al. (1997); Veyrat et al. (1997); Perollier et al. (1997).

Experimental top

Magnesium (0.4 g, 15.6 mmol) was added to 15 ml of anhydrous THF. A solution of bromobenzene (2.0 g, 12.5 mmol in 5 ml of THF) was added dropwise into the above mixture. Once the reaction began, the rest of the bromobenzene solution was added at a rate that maintained a gentle reflux. When the addition of the bromobenzene solution was complete, the mixture was refluxed for 20 min, and was then cooled to 273 K. (1R,3S)-Methyl-3-(1,3-dithian-2-yl)-2,2-dimethylcyclopropane carboxylate (5 mmol) (Mazzanti et al., 1997; Veyrat et al., 1997; Perollier et al., 1997) was dissolved in 5 ml of anhydrous THF and added to the prepared Grignard mixture. After the solution of carboxylate had been added, the resulting mixture was stirred at room temperature for an additional 24 h. The reaction was quenched with saturated NH₄Cl (aq), and the mixture was extracted several times with Et₂O. The organic phases were combined, dried over MgSO₄ and concentrated under reduced pressure. The residual yellow solid was purified by recrystallization in Et₂O to yield compound (I) as colourless crystals. Colourless solid, m.p. 427 K; [α]₂₀^D =+19.93 (c 0.03, CHCl₃).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2000); cell refinement: RAPID-AUTO (Rigaku, 2000); data reduction: CrystalStructure (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 30% probability displacement ellipsoids for non-H atoms.

[(1R,3S)-3-(1,3-Dithian-2-yl)-2,2- dimethylcyclopropyl]diphenylmethanol top

Crystal data top

C₂₂H₂₆OS₂	F(000) = 396
M_r = 370.55	D_x = 1.214 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7560 reflections
a = 9.5578 (19) Å	θ = 2.2–27.5°
b = 11.199 (2) Å	µ = 0.27 mm⁻¹
c = 9.6512 (19) Å	T = 123 K
β = 101.14 (3)°	Block, colourless
V = 1013.6 (4) Å³	0.40 × 0.40 × 0.30 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4303 independent reflections
Radiation source: fine-focus sealed tube	2920 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°, θ_min = 2.2°
ω scans	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −14→14
T_min = 0.900, T_max = 0.924	l = −12→12
4303 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.0379P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.084	(Δ/σ)_max = 0.001
S = 0.84	Δρ_max = 0.28 e Å⁻³
4303 reflections	Δρ_min = −0.30 e Å⁻³
229 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.046 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1878 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.05 (7)

Crystal data top

C₂₂H₂₆OS₂	V = 1013.6 (4) Å³
M_r = 370.55	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.5578 (19) Å	µ = 0.27 mm⁻¹
b = 11.199 (2) Å	T = 123 K
c = 9.6512 (19) Å	0.40 × 0.40 × 0.30 mm
β = 101.14 (3)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	4303 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2920 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.924	R_int = 0.000
4303 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.084	Δρ_max = 0.28 e Å⁻³
S = 0.84	Δρ_min = −0.30 e Å⁻³
4303 reflections	Absolute structure: Flack (1983), 1878 Friedel pairs
229 parameters	Absolute structure parameter: 0.05 (7)
1 restraint

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.6857 (3)	0.2287 (2)	0.2178 (3)	0.0254 (6)
H1	0.6517	0.2825	0.1355	0.030*
C2	0.6466 (3)	0.2775 (2)	0.3516 (3)	0.0287 (7)
C3	0.8003 (3)	0.2893 (2)	0.3280 (3)	0.0238 (6)
H3	0.8246	0.3717	0.3005	0.029*
C4	0.5595 (3)	0.3923 (3)	0.3379 (3)	0.0462 (9)
H4A	0.4577	0.3727	0.3176	0.069*
H4B	0.5827	0.4407	0.2609	0.069*
H4C	0.5822	0.4373	0.4265	0.069*
C5	0.6172 (3)	0.1950 (3)	0.4668 (3)	0.0369 (8)
H5A	0.5156	0.1745	0.4492	0.055*
H5B	0.6432	0.2350	0.5585	0.055*
H5C	0.6739	0.1220	0.4674	0.055*
C6	0.9233 (2)	0.2264 (2)	0.4217 (3)	0.0236 (6)
H6	0.8867	0.1549	0.4656	0.028*
C7	1.1962 (3)	0.1241 (3)	0.4492 (3)	0.0351 (7)
H7A	1.1632	0.0529	0.4944	0.042*
H7B	1.2751	0.0987	0.4028	0.042*
C8	1.2536 (3)	0.2153 (2)	0.5636 (3)	0.0354 (8)
H8A	1.3404	0.1827	0.6245	0.042*
H8B	1.2811	0.2887	0.5184	0.042*
C9	1.1470 (3)	0.2472 (3)	0.6542 (3)	0.0354 (7)
H9A	1.1958	0.2940	0.7366	0.042*
H9B	1.1109	0.1729	0.6902	0.042*
C10	0.6776 (3)	0.0972 (2)	0.1726 (3)	0.0235 (6)
C11	0.7437 (3)	0.0754 (2)	0.0414 (3)	0.0258 (6)
C12	0.7434 (3)	−0.0429 (3)	−0.0102 (3)	0.0389 (8)
H12	0.6995	−0.1044	0.0341	0.047*
C13	0.8053 (3)	−0.0705 (3)	−0.1232 (3)	0.0479 (9)
H13	0.8059	−0.1507	−0.1551	0.057*
C14	0.8676 (3)	0.0196 (4)	−0.1912 (3)	0.0522 (10)
H14	0.9091	0.0014	−0.2705	0.063*
C15	0.8679 (4)	0.1346 (3)	−0.1422 (4)	0.0537 (10)
H15	0.9100	0.1958	−0.1885	0.064*
C16	0.8079 (3)	0.1635 (3)	−0.0258 (3)	0.0404 (8)
H16	0.8108	0.2435	0.0074	0.048*
C17	0.5212 (3)	0.0589 (2)	0.1427 (3)	0.0259 (6)
C18	0.4713 (3)	−0.0319 (3)	0.2171 (3)	0.0345 (7)
H18	0.5356	−0.0737	0.2880	0.041*
C19	0.3262 (3)	−0.0628 (3)	0.1886 (3)	0.0412 (8)
H19	0.2933	−0.1268	0.2385	0.049*
C20	0.2309 (3)	−0.0007 (3)	0.0882 (3)	0.0392 (8)
H20	0.1323	−0.0203	0.0713	0.047*
C21	0.2790 (3)	0.0895 (3)	0.0129 (3)	0.0410 (8)
H21	0.2141	0.1313	−0.0575	0.049*
C22	0.4234 (3)	0.1196 (3)	0.0402 (3)	0.0370 (8)
H22	0.4559	0.1825	−0.0117	0.044*
O1	0.75071 (18)	0.02068 (15)	0.28301 (18)	0.0294 (5)
H2	0.8381	0.0324	0.2863	0.035*
S1	1.05026 (7)	0.17887 (6)	0.31479 (7)	0.02959 (18)
S2	0.99674 (7)	0.33324 (6)	0.55984 (8)	0.0331 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0253 (14)	0.0246 (14)	0.0234 (16)	0.0024 (12)	−0.0025 (12)	0.0004 (11)
C2	0.0194 (14)	0.0317 (15)	0.0309 (17)	0.0023 (12)	−0.0056 (12)	−0.0089 (13)
C3	0.0195 (13)	0.0240 (14)	0.0248 (15)	0.0010 (11)	−0.0030 (11)	−0.0005 (11)
C4	0.0302 (17)	0.0495 (19)	0.053 (2)	0.0138 (15)	−0.0065 (15)	−0.0172 (16)
C5	0.0221 (14)	0.058 (2)	0.0314 (16)	−0.0069 (14)	0.0060 (12)	−0.0125 (16)
C6	0.0179 (13)	0.0270 (14)	0.0247 (15)	0.0028 (11)	0.0008 (11)	−0.0022 (11)
C7	0.0208 (15)	0.0375 (17)	0.045 (2)	−0.0002 (12)	0.0011 (13)	−0.0007 (14)
C8	0.0220 (15)	0.0344 (18)	0.046 (2)	−0.0034 (13)	−0.0026 (14)	0.0076 (14)
C9	0.0328 (16)	0.0335 (16)	0.0338 (18)	−0.0009 (14)	−0.0089 (14)	−0.0005 (13)
C10	0.0230 (14)	0.0218 (14)	0.0230 (15)	0.0046 (12)	−0.0021 (11)	0.0027 (11)
C11	0.0221 (14)	0.0318 (15)	0.0216 (14)	0.0074 (13)	−0.0008 (11)	0.0014 (12)
C12	0.0363 (18)	0.0429 (18)	0.0362 (18)	0.0034 (15)	0.0036 (14)	−0.0071 (15)
C13	0.0389 (19)	0.068 (3)	0.036 (2)	0.0096 (18)	0.0057 (16)	−0.0185 (19)
C14	0.0364 (19)	0.093 (3)	0.0271 (18)	0.021 (2)	0.0066 (15)	−0.013 (2)
C15	0.052 (2)	0.069 (3)	0.047 (2)	0.0117 (18)	0.0268 (18)	0.0166 (18)
C16	0.0431 (18)	0.0439 (19)	0.0360 (18)	0.0079 (17)	0.0121 (14)	0.0093 (16)
C17	0.0306 (15)	0.0253 (15)	0.0207 (14)	0.0019 (12)	0.0027 (12)	−0.0046 (12)
C18	0.0322 (16)	0.0349 (17)	0.0321 (17)	−0.0011 (14)	−0.0044 (13)	0.0055 (13)
C19	0.0405 (19)	0.0399 (18)	0.0406 (19)	−0.0124 (15)	0.0013 (15)	0.0031 (15)
C20	0.0277 (16)	0.050 (2)	0.0367 (19)	−0.0058 (15)	−0.0003 (14)	−0.0071 (15)
C21	0.0308 (17)	0.051 (2)	0.0378 (19)	0.0016 (16)	−0.0032 (14)	0.0019 (15)
C22	0.0334 (17)	0.0415 (18)	0.0338 (18)	−0.0031 (14)	0.0005 (14)	0.0093 (14)
O1	0.0285 (11)	0.0267 (10)	0.0287 (11)	0.0028 (8)	−0.0053 (9)	0.0036 (9)
S1	0.0226 (3)	0.0370 (4)	0.0294 (4)	0.0013 (3)	0.0058 (3)	0.0009 (3)
S2	0.0289 (4)	0.0306 (4)	0.0356 (4)	0.0023 (3)	−0.0043 (3)	−0.0068 (4)

Geometric parameters (Å, º) top

C1—C2	1.515 (4)	C9—H9B	0.9900
C1—C3	1.531 (3)	C10—O1	1.439 (3)
C1—C10	1.533 (4)	C10—C17	1.529 (4)
C1—H1	1.0000	C10—C11	1.540 (4)
C2—C5	1.513 (4)	C11—C16	1.387 (4)
C2—C4	1.523 (4)	C11—C12	1.415 (4)
C2—C3	1.536 (4)	C12—C13	1.372 (4)
C3—C6	1.511 (3)	C12—H12	0.9500
C3—H3	1.0000	C13—C14	1.398 (5)
C4—H4A	0.9800	C13—H13	0.9500
C4—H4B	0.9800	C14—C15	1.371 (5)
C4—H4C	0.9800	C14—H14	0.9500
C5—H5A	0.9800	C15—C16	1.395 (4)
C5—H5B	0.9800	C15—H15	0.9500
C5—H5C	0.9800	C16—H16	0.9500
C6—S1	1.818 (3)	C17—C18	1.382 (4)
C6—S2	1.827 (3)	C17—C22	1.399 (4)
C6—H6	1.0000	C18—C19	1.404 (4)
C7—C8	1.526 (4)	C18—H18	0.9500
C7—S1	1.818 (3)	C19—C20	1.382 (4)
C7—H7A	0.9900	C19—H19	0.9500
C7—H7B	0.9900	C20—C21	1.375 (4)
C8—C9	1.508 (4)	C20—H20	0.9500
C8—H8A	0.9900	C21—C22	1.396 (4)
C8—H8B	0.9900	C21—H21	0.9500
C9—S2	1.821 (3)	C22—H22	0.9500
C9—H9A	0.9900	O1—H2	0.8400

C2—C1—C3	60.55 (17)	S2—C9—H9A	109.0
C2—C1—C10	125.6 (2)	C8—C9—H9B	109.0
C3—C1—C10	127.8 (2)	S2—C9—H9B	109.0
C2—C1—H1	111.3	H9A—C9—H9B	107.8
C3—C1—H1	111.3	O1—C10—C17	106.8 (2)
C10—C1—H1	111.3	O1—C10—C1	111.8 (2)
C5—C2—C1	121.2 (2)	C17—C10—C1	108.5 (2)
C5—C2—C4	113.8 (3)	O1—C10—C11	107.24 (19)
C1—C2—C4	116.8 (2)	C17—C10—C11	110.0 (2)
C5—C2—C3	118.7 (2)	C1—C10—C11	112.4 (2)
C1—C2—C3	60.24 (18)	C16—C11—C12	118.2 (3)
C4—C2—C3	115.9 (2)	C16—C11—C10	124.1 (2)
C6—C3—C1	125.3 (2)	C12—C11—C10	117.7 (2)
C6—C3—C2	121.8 (2)	C13—C12—C11	121.2 (3)
C1—C3—C2	59.21 (17)	C13—C12—H12	119.4
C6—C3—H3	113.3	C11—C12—H12	119.4
C1—C3—H3	113.3	C12—C13—C14	119.9 (3)
C2—C3—H3	113.3	C12—C13—H13	120.0
C2—C4—H4A	109.5	C14—C13—H13	120.0
C2—C4—H4B	109.5	C15—C14—C13	119.2 (3)
H4A—C4—H4B	109.5	C15—C14—H14	120.4
C2—C4—H4C	109.5	C13—C14—H14	120.4
H4A—C4—H4C	109.5	C14—C15—C16	121.5 (3)
H4B—C4—H4C	109.5	C14—C15—H15	119.3
C2—C5—H5A	109.5	C16—C15—H15	119.3
C2—C5—H5B	109.5	C11—C16—C15	120.0 (3)
H5A—C5—H5B	109.5	C11—C16—H16	120.0
C2—C5—H5C	109.5	C15—C16—H16	120.0
H5A—C5—H5C	109.5	C18—C17—C22	118.3 (3)
H5B—C5—H5C	109.5	C18—C17—C10	122.1 (2)
C3—C6—S1	108.90 (19)	C22—C17—C10	119.5 (2)
C3—C6—S2	106.04 (18)	C17—C18—C19	120.4 (3)
S1—C6—S2	113.65 (13)	C17—C18—H18	119.8
C3—C6—H6	109.4	C19—C18—H18	119.8
S1—C6—H6	109.4	C20—C19—C18	120.4 (3)
S2—C6—H6	109.4	C20—C19—H19	119.8
C8—C7—S1	114.18 (19)	C18—C19—H19	119.8
C8—C7—H7A	108.7	C21—C20—C19	119.9 (3)
S1—C7—H7A	108.7	C21—C20—H20	120.1
C8—C7—H7B	108.7	C19—C20—H20	120.1
S1—C7—H7B	108.7	C20—C21—C22	119.8 (3)
H7A—C7—H7B	107.6	C20—C21—H21	120.1
C9—C8—C7	112.9 (2)	C22—C21—H21	120.1
C9—C8—H8A	109.0	C21—C22—C17	121.2 (3)
C7—C8—H8A	109.0	C21—C22—H22	119.4
C9—C8—H8B	109.0	C17—C22—H22	119.4
C7—C8—H8B	109.0	C10—O1—H2	105.8
H8A—C8—H8B	107.8	C7—S1—C6	101.43 (13)
C8—C9—S2	113.0 (2)	C9—S2—C6	99.98 (13)
C8—C9—H9A	109.0

C3—C1—C2—C5	−107.5 (3)	C1—C10—C11—C12	179.7 (2)
C10—C1—C2—C5	10.0 (4)	C16—C11—C12—C13	0.4 (4)
C3—C1—C2—C4	106.0 (3)	C10—C11—C12—C13	−177.4 (3)
C10—C1—C2—C4	−136.5 (3)	C11—C12—C13—C14	−1.4 (4)
C10—C1—C2—C3	117.5 (3)	C12—C13—C14—C15	1.1 (5)
C2—C1—C3—C6	109.2 (3)	C13—C14—C15—C16	0.1 (5)
C10—C1—C3—C6	−4.9 (4)	C12—C11—C16—C15	0.9 (4)
C10—C1—C3—C2	−114.1 (3)	C10—C11—C16—C15	178.5 (3)
C5—C2—C3—C6	−3.5 (4)	C14—C15—C16—C11	−1.1 (5)
C1—C2—C3—C6	−115.0 (3)	O1—C10—C17—C18	1.3 (3)
C4—C2—C3—C6	137.5 (3)	C1—C10—C17—C18	−119.4 (3)
C5—C2—C3—C1	111.5 (3)	C11—C10—C17—C18	117.4 (3)
C4—C2—C3—C1	−107.5 (3)	O1—C10—C17—C22	179.1 (2)
C1—C3—C6—S1	71.5 (3)	C1—C10—C17—C22	58.5 (3)
C2—C3—C6—S1	144.1 (2)	C11—C10—C17—C22	−64.8 (3)
C1—C3—C6—S2	−165.9 (2)	C22—C17—C18—C19	0.8 (4)
C2—C3—C6—S2	−93.3 (3)	C10—C17—C18—C19	178.6 (3)
S1—C7—C8—C9	66.4 (3)	C17—C18—C19—C20	−1.7 (5)
C7—C8—C9—S2	−69.4 (3)	C18—C19—C20—C21	1.9 (5)
C2—C1—C10—O1	−51.7 (3)	C19—C20—C21—C22	−1.3 (5)
C3—C1—C10—O1	26.2 (4)	C20—C21—C22—C17	0.4 (5)
C2—C1—C10—C17	65.9 (3)	C18—C17—C22—C21	−0.2 (4)
C3—C1—C10—C17	143.8 (3)	C10—C17—C22—C21	−178.1 (3)
C2—C1—C10—C11	−172.3 (2)	C8—C7—S1—C6	−55.9 (2)
C3—C1—C10—C11	−94.4 (3)	C3—C6—S1—C7	173.11 (18)
O1—C10—C11—C16	−121.1 (3)	S2—C6—S1—C7	55.16 (17)
C17—C10—C11—C16	123.0 (3)	C8—C9—S2—C6	61.1 (2)
C1—C10—C11—C16	2.1 (3)	C3—C6—S2—C9	−176.75 (19)
O1—C10—C11—C12	56.5 (3)	S1—C6—S2—C9	−57.17 (18)
C17—C10—C11—C12	−59.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H2···S1	0.84	2.58	3.330 (2)	149
C7—H7A···S2ⁱ	0.99	2.89	3.736 (3)	144
C9—H9A···O1ⁱⁱ	0.99	2.60	3.236 (3)	122

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

Experimental details

Crystal data
Chemical formula	C₂₂H₂₆OS₂
M_r	370.55
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	123
a, b, c (Å)	9.5578 (19), 11.199 (2), 9.6512 (19)
β (°)	101.14 (3)
V (Å³)	1013.6 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.40 × 0.40 × 0.30

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.900, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	4303, 4303, 2920
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.084, 0.84
No. of reflections	4303
No. of parameters	229
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.30
Absolute structure	Flack (1983), 1878 Friedel pairs
Absolute structure parameter	0.05 (7)

Computer programs: RAPID-AUTO (Rigaku, 2000), CrystalStructure (Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H2···S1	0.84	2.58	3.330 (2)	149.1
C7—H7A···S2ⁱ	0.99	2.89	3.736 (3)	144.0
C9—H9A···O1ⁱⁱ	0.99	2.60	3.236 (3)	121.7

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

Acknowledgements

Financial support from the National Natural Science Foundation of China (grant Nos. 20472111 and20742004) is gratefully acknowledged.

References

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