5,8-Bis(3-hy­droxy-3-methyl­but-1-yn-1-yl)-2,11-dithia­[3.3]paracyclo­phane

Wu, D.; Huang, J.

doi:10.1107/S1600536811048446

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3374

https://doi.org/10.1107/S1600536811048446

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5,8-Bis(3-hydroxy-3-methylbut-1-yn-1-yl)-2,11-dithia[3.3]paracyclophane

Di Wu ^a ^* and Jie Huang ^a

^aKey Laboratory of Pesticide and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: wudi19871208@163.com

(Received 24 October 2011; accepted 15 November 2011; online 19 November 2011)

In the crystal structure of the title compound [systematic name: 2,2′-dimethyl-4,4′-(3,10-dithiatricyclo[10.2.2.2^5,8]octadeca-1(14),5,7,12,15,17-hexaen-6,17-diyl)dibut-3-yn-2-ol], C₂₆H₂₈O₂S₂, molecules are linked by O—H⋯O hydrogen bonds, forming a tubular chain which runs parallel to the b axis. The tubular structure is reinforced by π–π stacking interactions [centroid–centroid distance = 3.6332(16Å].

Related literature

For the preparation of the title compound, see: Jin & Lu (2010 ). For molecular building blocks associated with para-cyclophanes see: Xu et al. (2008 ).

Experimental

Crystal data

C₂₆H₂₈O₂S₂
M_r = 436.60
Monoclinic, C 2/c
a = 17.1059 (5) Å
b = 11.8596 (4) Å
c = 24.5073 (10) Å
β = 108.113 (2)°
V = 4725.4 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 298 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.943, T_max = 0.976
14956 measured reflections
4646 independent reflections
2596 reflections with I > 2σ(I)
R_int = 0.080

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.149
S = 0.92
4646 reflections
277 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.99	2.777 (4)	161
O2—H2⋯O1ⁱⁱ	0.82	2.03	2.808 (3)	158
Symmetry codes: (i) $[-x+2, y-1, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811048446/go2035sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048446/go2035Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048446/go2035Isup3.cml

checkCIF report

Comment top

The molecular building block associated with para-cyclophanes are widely used in chiral catalysis, the design of new optoelectronic (NLO) materials, electron transfer processes, and molecular electronics, polymer chemistry and materials science, and even organic solar cells.(Xu et al., 2008)

Up to now, the dithia[3.3]paracyclophane building blocks, which are synthetically more accessible, have received less attention. Here we report the crystal structure of the title compound (Fig. 1).

The molecules are linked into pairs by the O1-H1···.O2 hydrogen bond, Table 1. These pairs are then linked together by the O2-H2···O1, Table 1, and a symmetry related hydrogen bond to form a tube which runs parallel to the b-axis.

This tubular structure is re-inforced by π–π stacking between the phenyl ring containing C1 and its symmetry related ring in the molecule at (5/2+x,1/2-y,1/2+z), centroid to centroid distance, 3.6332(16Å, perpendicular 3.4658 (12)Å and a slippage of 1.0901Å.

Within the molecule the two phenyl rings have a centroid to centoid distance of 3.2621 (18)Å, an average perpendicular spacing of 3.2402Å with a slippage of 0.3773Å.

Related literature top

For the preparation of the title compound, see: Jin & Lu (2010). For molecular building blocks associated with para-cyclophanes see: Xu et al. (2008).

Experimental top

To a stirred solution of appropriate 5,8-dibromo-2,11-dithia[3,3]paracyclophane and 2-methylbut-3-yn-2-ol (in the molecular ratio 1: 4) in THF, ⁱPr₂NH, Pd(PPh₃)₂Cl₂(10 mol%) and CuI(10 mol%) was added under N₂, the mixture was refluxed for 48 h. The cooled reaction mixture was filtered, diluted with CH₂Cl₂ and washed with water. The organic phase was dried with Na₂S0₄, filtered, and the solvent was removed from the filtrate in vacuo. The crude products were purified by column chromatography on silica gel to yield diols (Jin and Lu 2010).

Structure description top

Up to now, the dithia[3.3]paracyclophane building blocks, which are synthetically more accessible, have received less attention. Here we report the crystal structure of the title compound (Fig. 1).

Within the molecule the two phenyl rings have a centroid to centoid distance of 3.2621 (18)Å, an average perpendicular spacing of 3.2402Å with a slippage of 0.3773Å.

For the preparation of the title compound, see: Jin & Lu (2010). For molecular building blocks associated with para-cyclophanes see: Xu et al. (2008).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of (I), showing the chains generated by the O—H···O hydrogen bonds running parallel to the b-axis.

2,2'-dimethyl-4,4'-(3,10-dithiatricyclo[10.2.2.2^5,8]octadeca- 1(14),5,7,12,15,17-hexaen-6,17-diyl)dibut-3-yn-2-ol top

Crystal data top

C₂₆H₂₈O₂S₂	F(000) = 1856
M_r = 436.60	D_x = 1.227 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1923 reflections
a = 17.1059 (5) Å	θ = 2.4–21.8°
b = 11.8596 (4) Å	µ = 0.25 mm⁻¹
c = 24.5073 (10) Å	T = 298 K
β = 108.113 (2)°	Block, colourless
V = 4725.4 (3) Å³	0.20 × 0.10 × 0.10 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	4646 independent reflections
Radiation source: fine-focus sealed tube	2596 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
φ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −21→20
T_min = 0.943, T_max = 0.976	k = −12→14
14956 measured reflections	l = −30→29

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 0.92	w = 1/[σ²(F_o²) + (0.0638P)²] where P = (F_o² + 2F_c²)/3
4646 reflections	(Δ/σ)_max < 0.001
277 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₆H₂₈O₂S₂	V = 4725.4 (3) Å³
M_r = 436.60	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 17.1059 (5) Å	µ = 0.25 mm⁻¹
b = 11.8596 (4) Å	T = 298 K
c = 24.5073 (10) Å	0.20 × 0.10 × 0.10 mm
β = 108.113 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4646 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2596 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.976	R_int = 0.080
14956 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 0.92	Δρ_max = 0.27 e Å⁻³
4646 reflections	Δρ_min = −0.22 e Å⁻³
277 parameters

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	1.00428 (17)	0.1057 (2)	0.17980 (12)	0.0432 (7)
C2	0.91906 (18)	0.1194 (2)	0.15785 (12)	0.0439 (7)
C3	0.88756 (18)	0.2274 (2)	0.15218 (12)	0.0467 (7)
H3	0.8308	0.2376	0.1396	0.056*
C4	0.93876 (18)	0.3215 (2)	0.16488 (12)	0.0427 (7)
C5	1.02399 (17)	0.3086 (2)	0.18464 (12)	0.0432 (7)
C6	1.05457 (18)	0.1999 (2)	0.19349 (12)	0.0479 (8)
H6	1.1110	0.1896	0.2092	0.057*
C7	0.86268 (19)	0.0188 (2)	0.13702 (14)	0.0607 (9)
H7A	0.8323	0.0059	0.1639	0.073*
H7B	0.8966	−0.0472	0.1380	0.073*
C8	0.8537 (3)	0.0327 (3)	0.01972 (17)	0.0937 (13)
H8A	0.8882	−0.0341	0.0274	0.112*
H8B	0.8182	0.0278	−0.0197	0.112*
C9	0.9086 (2)	0.1353 (3)	0.02529 (14)	0.0646 (9)
C10	0.8766 (2)	0.2425 (3)	0.01542 (15)	0.0699 (10)
H10	0.8201	0.2520	−0.0005	0.084*
C11	0.9268 (2)	0.3362 (3)	0.02867 (14)	0.0615 (9)
H11	0.9034	0.4077	0.0221	0.074*
C12	1.0111 (2)	0.3257 (3)	0.05155 (13)	0.0555 (8)
C13	1.0431 (2)	0.2181 (3)	0.05674 (14)	0.0658 (9)
H13	1.0999	0.2083	0.0691	0.079*
C14	0.9928 (2)	0.1248 (3)	0.04403 (14)	0.0644 (9)
H14	1.0162	0.0533	0.0482	0.077*
C15	1.0646 (2)	0.4279 (3)	0.07326 (15)	0.0728 (10)
H15A	1.0291	0.4911	0.0742	0.087*
H15B	1.0930	0.4460	0.0457	0.087*
C16	1.08110 (18)	0.4088 (2)	0.19252 (14)	0.0566 (9)
H16A	1.1188	0.4074	0.2314	0.068*
H16B	1.0486	0.4772	0.1885	0.068*
C17	1.04174 (18)	−0.0044 (2)	0.18399 (12)	0.0488 (8)
C18	1.07335 (18)	−0.0932 (3)	0.18470 (13)	0.0528 (8)
C19	1.1114 (2)	−0.2046 (3)	0.18242 (14)	0.0586 (9)
C20	1.0999 (3)	−0.2365 (3)	0.12062 (17)	0.1061 (15)
H20A	1.1261	−0.3076	0.1194	0.159*
H20B	1.1241	−0.1796	0.1030	0.159*
H20C	1.0423	−0.2424	0.1002	0.159*
C21	1.2026 (2)	−0.2005 (3)	0.21646 (18)	0.0865 (12)
H21A	1.2090	−0.1789	0.2554	0.130*
H21B	1.2297	−0.1465	0.1994	0.130*
H21C	1.2266	−0.2736	0.2161	0.130*
C22	0.90358 (18)	0.4331 (3)	0.15376 (13)	0.0492 (8)
C23	0.87791 (18)	0.5261 (3)	0.14457 (14)	0.0550 (8)
C24	0.8459 (2)	0.6417 (3)	0.13498 (17)	0.0758 (12)
C25	0.8404 (3)	0.6801 (3)	0.0756 (2)	0.140 (2)
H25A	0.8150	0.7531	0.0687	0.210*
H25B	0.8080	0.6273	0.0480	0.210*
H25C	0.8947	0.6843	0.0720	0.210*
C26	0.7637 (2)	0.6443 (4)	0.1460 (2)	0.135 (2)
H26A	0.7712	0.6261	0.1855	0.203*
H26B	0.7274	0.5902	0.1217	0.203*
H26C	0.7402	0.7183	0.1378	0.203*
O1	1.07259 (14)	−0.28867 (17)	0.20705 (10)	0.0672 (6)
H1	1.0921	−0.2870	0.2421	0.101*
O2	0.90016 (13)	0.71742 (18)	0.17522 (11)	0.0744 (7)
H2	0.9478	0.7048	0.1765	0.112*
S1	0.79017 (5)	0.03053 (7)	0.06626 (4)	0.0678 (3)
S2	1.14046 (5)	0.41556 (7)	0.14312 (4)	0.0590 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0508 (18)	0.0408 (18)	0.0387 (18)	0.0058 (14)	0.0149 (15)	0.0022 (13)
C2	0.0529 (19)	0.0422 (17)	0.0369 (17)	0.0019 (14)	0.0146 (15)	0.0054 (13)
C3	0.0460 (17)	0.0450 (19)	0.051 (2)	0.0045 (14)	0.0173 (16)	0.0028 (15)
C4	0.0547 (19)	0.0374 (17)	0.0399 (18)	0.0096 (14)	0.0202 (15)	−0.0001 (13)
C5	0.0491 (18)	0.0392 (17)	0.0419 (18)	0.0000 (14)	0.0148 (15)	−0.0077 (13)
C6	0.0467 (17)	0.0476 (19)	0.048 (2)	0.0069 (15)	0.0132 (15)	−0.0037 (14)
C7	0.057 (2)	0.0465 (19)	0.075 (2)	−0.0017 (16)	0.0148 (18)	0.0075 (17)
C8	0.109 (3)	0.088 (3)	0.088 (3)	−0.035 (2)	0.036 (3)	−0.036 (2)
C9	0.074 (3)	0.075 (3)	0.048 (2)	−0.011 (2)	0.0235 (19)	−0.0121 (18)
C10	0.059 (2)	0.089 (3)	0.065 (3)	−0.003 (2)	0.024 (2)	0.001 (2)
C11	0.067 (2)	0.068 (2)	0.052 (2)	0.0091 (19)	0.0225 (19)	0.0164 (18)
C12	0.063 (2)	0.058 (2)	0.045 (2)	0.0012 (17)	0.0159 (17)	0.0096 (16)
C13	0.062 (2)	0.071 (3)	0.058 (2)	0.004 (2)	0.0083 (19)	−0.0029 (19)
C14	0.084 (3)	0.058 (2)	0.046 (2)	0.003 (2)	0.013 (2)	−0.0098 (17)
C15	0.077 (2)	0.063 (2)	0.075 (3)	−0.0068 (19)	0.020 (2)	0.0167 (19)
C16	0.0585 (19)	0.0420 (18)	0.068 (2)	0.0066 (15)	0.0177 (18)	−0.0097 (16)
C17	0.0575 (19)	0.0392 (18)	0.0475 (19)	−0.0003 (15)	0.0131 (16)	0.0013 (15)
C18	0.0551 (19)	0.047 (2)	0.052 (2)	0.0068 (16)	0.0108 (16)	0.0014 (16)
C19	0.070 (2)	0.0448 (19)	0.059 (2)	0.0146 (16)	0.0179 (19)	0.0058 (16)
C20	0.170 (4)	0.077 (3)	0.074 (3)	0.028 (3)	0.042 (3)	−0.012 (2)
C21	0.061 (2)	0.083 (3)	0.115 (4)	0.020 (2)	0.028 (2)	0.027 (2)
C22	0.0521 (19)	0.0460 (19)	0.051 (2)	0.0065 (15)	0.0186 (16)	−0.0078 (15)
C23	0.0471 (18)	0.045 (2)	0.068 (2)	0.0087 (15)	0.0100 (17)	−0.0118 (16)
C24	0.069 (2)	0.044 (2)	0.083 (3)	0.0186 (17)	−0.022 (2)	−0.0229 (19)
C25	0.212 (6)	0.058 (3)	0.087 (4)	0.002 (3)	−0.046 (4)	−0.002 (2)
C26	0.056 (2)	0.111 (4)	0.201 (6)	0.028 (2)	−0.014 (3)	−0.088 (4)
O1	0.0762 (16)	0.0430 (13)	0.0763 (17)	0.0061 (11)	0.0145 (14)	0.0070 (12)
O2	0.0620 (14)	0.0477 (13)	0.0908 (19)	0.0060 (11)	−0.0093 (15)	−0.0242 (12)
S1	0.0540 (5)	0.0654 (6)	0.0772 (7)	−0.0130 (4)	0.0104 (5)	−0.0030 (5)
S2	0.0494 (5)	0.0500 (5)	0.0773 (7)	−0.0036 (4)	0.0194 (5)	−0.0010 (4)

Geometric parameters (Å, º) top

C1—C6	1.386 (4)	C15—S2	1.804 (3)
C1—C2	1.397 (4)	C15—H15A	0.9700
C1—C17	1.445 (4)	C15—H15B	0.9700
C2—C3	1.381 (4)	C16—S2	1.808 (3)
C2—C7	1.519 (4)	C16—H16A	0.9700
C3—C4	1.393 (4)	C16—H16B	0.9700
C3—H3	0.9300	C17—C18	1.181 (4)
C4—C5	1.395 (4)	C18—C19	1.481 (4)
C4—C22	1.444 (4)	C19—O1	1.431 (4)
C5—C6	1.383 (4)	C19—C20	1.514 (5)
C5—C16	1.512 (4)	C19—C21	1.525 (4)
C6—H6	0.9300	C20—H20A	0.9600
C7—S1	1.797 (3)	C20—H20B	0.9600
C7—H7A	0.9700	C20—H20C	0.9600
C7—H7B	0.9700	C21—H21A	0.9600
C8—C9	1.517 (5)	C21—H21B	0.9600
C8—S1	1.804 (4)	C21—H21C	0.9600
C8—H8A	0.9700	C22—C23	1.183 (4)
C8—H8B	0.9700	C23—C24	1.467 (4)
C9—C14	1.375 (4)	C24—O2	1.440 (4)
C9—C10	1.376 (5)	C24—C25	1.500 (6)
C10—C11	1.379 (4)	C24—C26	1.512 (5)
C10—H10	0.9300	C25—H25A	0.9600
C11—C12	1.381 (4)	C25—H25B	0.9600
C11—H11	0.9300	C25—H25C	0.9600
C12—C13	1.380 (4)	C26—H26A	0.9600
C12—C15	1.512 (4)	C26—H26B	0.9600
C13—C14	1.377 (4)	C26—H26C	0.9600
C13—H13	0.9300	O1—H1	0.8200
C14—H14	0.9300	O2—H2	0.8200

C6—C1—C2	119.7 (3)	S2—C15—H15B	108.2
C6—C1—C17	118.9 (3)	H15A—C15—H15B	107.3
C2—C1—C17	121.2 (3)	C5—C16—S2	115.1 (2)
C3—C2—C1	118.3 (3)	C5—C16—H16A	108.5
C3—C2—C7	120.5 (3)	S2—C16—H16A	108.5
C1—C2—C7	121.1 (3)	C5—C16—H16B	108.5
C2—C3—C4	121.5 (3)	S2—C16—H16B	108.5
C2—C3—H3	119.2	H16A—C16—H16B	107.5
C4—C3—H3	119.2	C18—C17—C1	176.4 (3)
C3—C4—C5	120.4 (2)	C17—C18—C19	177.1 (3)
C3—C4—C22	119.7 (3)	O1—C19—C18	109.8 (3)
C5—C4—C22	119.7 (3)	O1—C19—C20	108.4 (3)
C6—C5—C4	117.4 (3)	C18—C19—C20	109.8 (3)
C6—C5—C16	121.0 (3)	O1—C19—C21	108.7 (3)
C4—C5—C16	121.5 (2)	C18—C19—C21	109.8 (3)
C5—C6—C1	122.5 (3)	C20—C19—C21	110.3 (3)
C5—C6—H6	118.8	C19—C20—H20A	109.5
C1—C6—H6	118.8	C19—C20—H20B	109.5
C2—C7—S1	116.0 (2)	H20A—C20—H20B	109.5
C2—C7—H7A	108.3	C19—C20—H20C	109.5
S1—C7—H7A	108.3	H20A—C20—H20C	109.5
C2—C7—H7B	108.3	H20B—C20—H20C	109.5
S1—C7—H7B	108.3	C19—C21—H21A	109.5
H7A—C7—H7B	107.4	C19—C21—H21B	109.5
C9—C8—S1	115.6 (2)	H21A—C21—H21B	109.5
C9—C8—H8A	108.4	C19—C21—H21C	109.5
S1—C8—H8A	108.4	H21A—C21—H21C	109.5
C9—C8—H8B	108.4	H21B—C21—H21C	109.5
S1—C8—H8B	108.4	C23—C22—C4	177.2 (3)
H8A—C8—H8B	107.4	C22—C23—C24	178.2 (4)
C14—C9—C10	117.4 (3)	O2—C24—C23	110.1 (3)
C14—C9—C8	120.8 (4)	O2—C24—C25	107.9 (3)
C10—C9—C8	121.7 (4)	C23—C24—C25	110.3 (3)
C9—C10—C11	121.3 (3)	O2—C24—C26	107.6 (3)
C9—C10—H10	119.4	C23—C24—C26	108.2 (3)
C11—C10—H10	119.4	C25—C24—C26	112.7 (4)
C10—C11—C12	121.2 (3)	C24—C25—H25A	109.5
C10—C11—H11	119.4	C24—C25—H25B	109.5
C12—C11—H11	119.4	H25A—C25—H25B	109.5
C13—C12—C11	117.1 (3)	C24—C25—H25C	109.5
C13—C12—C15	121.9 (3)	H25A—C25—H25C	109.5
C11—C12—C15	120.8 (3)	H25B—C25—H25C	109.5
C14—C13—C12	121.3 (3)	C24—C26—H26A	109.5
C14—C13—H13	119.3	C24—C26—H26B	109.5
C12—C13—H13	119.3	H26A—C26—H26B	109.5
C9—C14—C13	121.3 (3)	C24—C26—H26C	109.5
C9—C14—H14	119.3	H26A—C26—H26C	109.5
C13—C14—H14	119.3	H26B—C26—H26C	109.5
C12—C15—S2	116.6 (2)	C19—O1—H1	109.5
C12—C15—H15A	108.2	C24—O2—H2	109.5
S2—C15—H15A	108.2	C7—S1—C8	103.91 (18)
C12—C15—H15B	108.2	C15—S2—C16	104.56 (16)

C6—C1—C2—C3	−2.0 (4)	S1—C8—C9—C10	−59.7 (4)
C17—C1—C2—C3	−176.6 (3)	C14—C9—C10—C11	−5.7 (5)
C6—C1—C2—C7	174.1 (3)	C8—C9—C10—C11	170.3 (3)
C17—C1—C2—C7	−0.6 (4)	C9—C10—C11—C12	1.0 (5)
C1—C2—C3—C4	3.4 (4)	C10—C11—C12—C13	4.4 (5)
C7—C2—C3—C4	−172.6 (3)	C10—C11—C12—C15	−171.8 (3)
C2—C3—C4—C5	−0.9 (4)	C11—C12—C13—C14	−5.1 (5)
C2—C3—C4—C22	174.8 (3)	C15—C12—C13—C14	171.1 (3)
C3—C4—C5—C6	−3.0 (4)	C10—C9—C14—C13	5.0 (5)
C22—C4—C5—C6	−178.7 (3)	C8—C9—C14—C13	−171.0 (3)
C3—C4—C5—C16	173.2 (3)	C12—C13—C14—C9	0.4 (5)
C22—C4—C5—C16	−2.5 (4)	C13—C12—C15—S2	−43.9 (4)
C4—C5—C6—C1	4.5 (4)	C11—C12—C15—S2	132.2 (3)
C16—C5—C6—C1	−171.7 (3)	C6—C5—C16—S2	64.3 (3)
C2—C1—C6—C5	−2.1 (4)	C4—C5—C16—S2	−111.7 (3)
C17—C1—C6—C5	172.7 (3)	C2—C7—S1—C8	66.4 (3)
C3—C2—C7—S1	47.5 (4)	C9—C8—S1—C7	−66.4 (3)
C1—C2—C7—S1	−128.4 (3)	C12—C15—S2—C16	−68.5 (3)
S1—C8—C9—C14	116.1 (3)	C5—C16—S2—C15	62.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.99	2.777 (4)	161
O2—H2···O1ⁱⁱ	0.82	2.03	2.808 (3)	158

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₈O₂S₂
M_r	436.60
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	17.1059 (5), 11.8596 (4), 24.5073 (10)
β (°)	108.113 (2)
V (Å³)	4725.4 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.943, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	14956, 4646, 2596
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.149, 0.92
No. of reflections	4646
No. of parameters	277
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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—H1···O2ⁱ	0.82	1.99	2.777 (4)	161
O2—H2···O1ⁱⁱ	0.82	2.03	2.808 (3)	158

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

Acknowledgements

The authors are grateful to Professor Sheng-Hua Liu for technical assistance with the structure analysis and Dr Xiang-Gao Meng for the data collection.

References

Bruker (2007). APEX2, SADABS, and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Jin, G. & Lu, Y. (2010). Acta Cryst. E66, o2144. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, J. W., Wang, W. L., Lin, T. T., Sun, Z. & Lai, Y. H. (2008). Supramol. Chem. 20, 723–730. Web of Science CSD CrossRef CAS Google Scholar