5,8-Bis(3-hy-droxy-3-methyl-but-1-yn-1-yl)-2,11-dithia-[3.3]paracyclo-phane.

IN THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND [SYSTEMATIC NAME: 2,2'-dimethyl-4,4'-(3,10-dithia-tricyclo-[10.2.2.2(5,8)]octa-deca-1(14),5,7,12,15,17-hexaen-6,17-di-yl)dibut-3-yn-2-ol], C(26)H(28)O(2)S(2), mol-ecules 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 inter-actions [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 = 436.60

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.149

S = 0.92

4646 reflections

277 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.22 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048446/go2035sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048446/go2035Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048446/go2035Isup3.cml

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

C26H28O2S2	F(000) = 1856
Mr = 436.60	Dx = 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

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

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(Fo2) + (0.0638P)2] where P = (Fo2 + 2Fc2)/3
4646 reflections	(Δ/σ)max < 0.001
277 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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

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

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .