5,8-Dibromo-14,15,17,18-tetra-methyl-2,11-dithia-[3.3]paracyclo-phane.

In the title mol-ecule [systematic name: 1(2),1(5)-dibromo-5(2),5(3),5(5),5(6)-tetramethyl-3,7-dithia-1,5(1,4)-dibenzenacyclooctaphane], C(20)H(22)Br(2)S(2), the distance between the centroids of the two benzene rings is 3.326 (4) Å, and their mean planes are almost parallel, forming a dihedral angle of 1.05 (7)°. The crystal packing exhibits no inter-molecular contacts shorter than the sum of van der Waals radii.

Related literature

For the preparation of the title compound, see: Wang et al. (2006 ▶). For the crystal structures of related compounds, see: Sun et al. (2008 ▶); Clément et al. (2009 ▶).

Experimental

Crystal data

C20H22Br2S2

M = 486.32

Monoclinic,

a = 15.298 (3) Å

b = 12.340 (2) Å

c = 10.0160 (18) Å

β = 91.864 (3)°

V = 1889.8 (6) Å3

Z = 4

Mo Kα radiation

μ = 4.51 mm−1

T = 298 K

0.23 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer

12364 measured reflections

3922 independent reflections

2690 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.099

S = 0.94

3922 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536810026760/cv2738sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026760/cv2738Isup2.hkl

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

C20H22Br2S2	F(000) = 976
Mr = 486.32	Dx = 1.709 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3874 reflections
a = 15.298 (3) Å	θ = 2.6–23.9°
b = 12.340 (2) Å	µ = 4.51 mm−1
c = 10.0160 (18) Å	T = 298 K
β = 91.864 (3)°	Block, colourless
V = 1889.8 (6) Å3	0.23 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEX diffractometer	2690 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.075
graphite	θmax = 26.5°, θmin = 2.1°
phi and ω scans	h = −12→19
12364 measured reflections	k = −15→14
3922 independent reflections	l = −12→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.049P)2] where P = (Fo2 + 2Fc2)/3
3922 reflections	(Δ/σ)max = 0.013
221 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.31 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
Br1	0.63291 (3)	−0.24847 (3)	0.69722 (4)	0.06216 (15)
Br2	0.86653 (3)	0.03415 (3)	1.12714 (4)	0.06978 (17)
C1	0.7941 (2)	−0.1625 (2)	0.8090 (3)	0.0407 (8)
C2	0.7035 (2)	−0.1602 (2)	0.8134 (3)	0.0398 (7)
C3	0.6607 (2)	−0.0921 (3)	0.8980 (3)	0.0445 (8)
H3	0.5998	−0.0911	0.8961	0.053*
C4	0.7068 (2)	−0.0249 (2)	0.9864 (3)	0.0436 (8)
C5	0.7961 (2)	−0.0389 (2)	0.9945 (3)	0.0434 (8)
C6	0.8387 (2)	−0.1043 (2)	0.9067 (3)	0.0448 (8)
H6	0.8994	−0.1094	0.9134	0.054*
C7	0.8438 (3)	−0.2189 (3)	0.7015 (4)	0.0579 (10)
H7A	0.8025	−0.2425	0.6320	0.069*
H7B	0.8713	−0.2832	0.7396	0.069*
C8	0.8677 (2)	−0.0337 (3)	0.5289 (3)	0.0493 (9)
H8A	0.9104	0.0117	0.4863	0.059*
H8B	0.8339	−0.0700	0.4585	0.059*
C9	0.8064 (2)	0.0394 (2)	0.6037 (3)	0.0336 (7)
C10	0.7159 (2)	0.0343 (2)	0.5758 (3)	0.0351 (7)
C11	0.65953 (19)	0.0939 (2)	0.6546 (3)	0.0344 (7)
C12	0.69283 (19)	0.1594 (2)	0.7578 (3)	0.0339 (7)
C13	0.7842 (2)	0.1727 (2)	0.7759 (3)	0.0340 (7)
C14	0.84008 (19)	0.1132 (2)	0.6990 (3)	0.0351 (7)
C15	0.6794 (2)	−0.0317 (3)	0.4589 (3)	0.0533 (9)
H15A	0.6190	−0.0132	0.4423	0.080*
H15B	0.6840	−0.1075	0.4796	0.080*
H15C	0.7119	−0.0162	0.3808	0.080*
C16	0.5615 (2)	0.0846 (3)	0.6279 (4)	0.0524 (9)
H16A	0.5425	0.0129	0.6503	0.079*
H16B	0.5482	0.0984	0.5351	0.079*
H16C	0.5318	0.1366	0.6815	0.079*
C17	0.9379 (2)	0.1285 (3)	0.7171 (4)	0.0555 (9)
H17A	0.9518	0.2041	0.7109	0.083*
H17B	0.9671	0.0894	0.6487	0.083*
H17C	0.9569	0.1016	0.8032	0.083*
C18	0.8205 (3)	0.2505 (3)	0.8816 (4)	0.0532 (9)
H18A	0.8832	0.2463	0.8850	0.080*
H18B	0.7986	0.2313	0.9671	0.080*
H18C	0.8028	0.3231	0.8593	0.080*
C19	0.6313 (2)	0.2168 (3)	0.8503 (4)	0.0478 (8)
H19A	0.5883	0.2561	0.7959	0.057*
H19B	0.6647	0.2697	0.9021	0.057*
C20	0.6574 (3)	0.0609 (3)	1.0634 (4)	0.0615 (10)
H20A	0.6990	0.1141	1.0978	0.074*
H20B	0.6310	0.0265	1.1393	0.074*
S1	0.92690 (6)	−0.13702 (8)	0.62621 (10)	0.0536 (2)
S2	0.57294 (6)	0.13011 (8)	0.96634 (10)	0.0572 (3)

	U11	U22	U33	U12	U13	U23
Br1	0.0655 (3)	0.0568 (3)	0.0643 (3)	−0.01722 (19)	0.0036 (2)	−0.00873 (18)
Br2	0.0857 (3)	0.0680 (3)	0.0542 (2)	0.0013 (2)	−0.0199 (2)	−0.00657 (19)
C1	0.046 (2)	0.0305 (16)	0.0458 (18)	0.0047 (15)	0.0098 (15)	0.0078 (14)
C2	0.049 (2)	0.0323 (16)	0.0383 (16)	−0.0038 (15)	0.0036 (14)	0.0041 (13)
C3	0.042 (2)	0.046 (2)	0.0456 (18)	−0.0015 (16)	0.0131 (15)	0.0034 (15)
C4	0.057 (2)	0.0401 (18)	0.0345 (16)	0.0056 (16)	0.0110 (15)	0.0066 (14)
C5	0.056 (2)	0.0407 (18)	0.0332 (16)	−0.0002 (16)	−0.0047 (15)	0.0063 (14)
C6	0.0415 (19)	0.0441 (19)	0.0489 (19)	0.0059 (15)	0.0015 (16)	0.0058 (16)
C7	0.059 (2)	0.0427 (19)	0.073 (3)	0.0030 (17)	0.021 (2)	−0.0133 (18)
C8	0.050 (2)	0.055 (2)	0.0434 (19)	0.0080 (17)	0.0094 (16)	0.0000 (15)
C9	0.0344 (18)	0.0372 (16)	0.0298 (14)	0.0046 (13)	0.0075 (12)	0.0063 (12)
C10	0.0409 (19)	0.0344 (16)	0.0301 (14)	−0.0028 (14)	−0.0002 (13)	0.0044 (12)
C11	0.0294 (17)	0.0383 (17)	0.0354 (15)	−0.0014 (13)	0.0021 (13)	0.0062 (13)
C12	0.0345 (17)	0.0303 (15)	0.0371 (15)	0.0023 (13)	0.0063 (13)	0.0041 (12)
C13	0.0367 (18)	0.0319 (15)	0.0333 (15)	−0.0031 (14)	−0.0006 (13)	0.0025 (12)
C14	0.0275 (16)	0.0396 (17)	0.0380 (16)	−0.0027 (13)	0.0004 (13)	0.0107 (13)
C15	0.052 (2)	0.057 (2)	0.050 (2)	−0.0062 (18)	−0.0023 (17)	−0.0121 (17)
C16	0.0309 (19)	0.064 (2)	0.062 (2)	−0.0022 (17)	−0.0018 (16)	−0.0051 (18)
C17	0.0326 (19)	0.065 (2)	0.068 (2)	−0.0055 (17)	−0.0016 (17)	−0.0039 (19)
C18	0.058 (2)	0.052 (2)	0.0492 (19)	−0.0119 (17)	−0.0032 (17)	−0.0060 (17)
C19	0.046 (2)	0.0409 (18)	0.057 (2)	0.0046 (16)	0.0119 (17)	−0.0045 (16)
C20	0.080 (3)	0.061 (2)	0.044 (2)	0.009 (2)	0.0095 (19)	−0.0028 (17)
S1	0.0425 (5)	0.0564 (6)	0.0626 (6)	0.0154 (4)	0.0150 (4)	0.0023 (4)
S2	0.0486 (6)	0.0601 (6)	0.0643 (6)	0.0107 (5)	0.0255 (5)	0.0004 (5)

Br1—C2	1.904 (3)	C11—C16	1.519 (4)
Br2—C5	1.909 (3)	C12—C13	1.413 (4)
C1—C6	1.378 (4)	C12—C19	1.517 (4)
C1—C2	1.388 (4)	C13—C14	1.381 (4)
C1—C7	1.509 (5)	C13—C18	1.521 (4)
C2—C3	1.374 (4)	C14—C17	1.514 (4)
C3—C4	1.389 (5)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.377 (5)	C15—H15C	0.9600
C4—C20	1.524 (5)	C16—H16A	0.9600
C5—C6	1.373 (5)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C7—S1	1.808 (4)	C17—H17A	0.9600
C7—H7A	0.9700	C17—H17B	0.9600
C7—H7B	0.9700	C17—H17C	0.9600
C8—C9	1.516 (4)	C18—H18A	0.9600
C8—S1	1.826 (3)	C18—H18B	0.9600
C8—H8A	0.9700	C18—H18C	0.9600
C8—H8B	0.9700	C19—S2	1.833 (4)
C9—C14	1.405 (4)	C19—H19A	0.9700
C9—C10	1.405 (4)	C19—H19B	0.9700
C10—C11	1.397 (4)	C20—S2	1.807 (4)
C10—C15	1.518 (4)	C20—H20A	0.9700
C11—C12	1.396 (4)	C20—H20B	0.9700
C6—C1—C2	116.1 (3)	C14—C13—C18	120.3 (3)
C6—C1—C7	119.9 (3)	C12—C13—C18	120.0 (3)
C2—C1—C7	124.0 (3)	C13—C14—C9	120.3 (3)
C3—C2—C1	121.9 (3)	C13—C14—C17	119.7 (3)
C3—C2—Br1	117.0 (3)	C9—C14—C17	120.1 (3)
C1—C2—Br1	121.0 (2)	C10—C15—H15A	109.5
C2—C3—C4	121.0 (3)	C10—C15—H15B	109.5
C2—C3—H3	119.5	H15A—C15—H15B	109.5
C4—C3—H3	119.5	C10—C15—H15C	109.5
C5—C4—C3	116.4 (3)	H15A—C15—H15C	109.5
C5—C4—C20	124.4 (3)	H15B—C15—H15C	109.5
C3—C4—C20	119.2 (3)	C11—C16—H16A	109.5
C6—C5—C4	121.8 (3)	C11—C16—H16B	109.5
C6—C5—Br2	117.0 (3)	H16A—C16—H16B	109.5
C4—C5—Br2	121.2 (3)	C11—C16—H16C	109.5
C5—C6—C1	121.8 (3)	H16A—C16—H16C	109.5
C5—C6—H6	119.1	H16B—C16—H16C	109.5
C1—C6—H6	119.1	C14—C17—H17A	109.5
C1—C7—S1	114.7 (2)	C14—C17—H17B	109.5
C1—C7—H7A	108.6	H17A—C17—H17B	109.5
S1—C7—H7A	108.6	C14—C17—H17C	109.5
C1—C7—H7B	108.6	H17A—C17—H17C	109.5
S1—C7—H7B	108.6	H17B—C17—H17C	109.5
H7A—C7—H7B	107.6	C13—C18—H18A	109.5
C9—C8—S1	117.1 (2)	C13—C18—H18B	109.5
C9—C8—H8A	108.0	H18A—C18—H18B	109.5
S1—C8—H8A	108.0	C13—C18—H18C	109.5
C9—C8—H8B	108.0	H18A—C18—H18C	109.5
S1—C8—H8B	108.0	H18B—C18—H18C	109.5
H8A—C8—H8B	107.3	C12—C19—S2	116.1 (2)
C14—C9—C10	120.1 (3)	C12—C19—H19A	108.3
C14—C9—C8	120.2 (3)	S2—C19—H19A	108.3
C10—C9—C8	119.8 (3)	C12—C19—H19B	108.3
C11—C10—C9	119.1 (3)	S2—C19—H19B	108.3
C11—C10—C15	120.0 (3)	H19A—C19—H19B	107.4
C9—C10—C15	120.9 (3)	C4—C20—S2	114.4 (2)
C12—C11—C10	120.4 (3)	C4—C20—H20A	108.7
C12—C11—C16	120.5 (3)	S2—C20—H20A	108.7
C10—C11—C16	119.0 (3)	C4—C20—H20B	108.7
C11—C12—C13	119.8 (3)	S2—C20—H20B	108.7
C11—C12—C19	120.2 (3)	H20A—C20—H20B	107.6
C13—C12—C19	119.9 (3)	C7—S1—C8	105.64 (18)
C14—C13—C12	119.7 (3)	C20—S2—C19	105.24 (19)
C6—C1—C2—C3	8.7 (4)	C9—C10—C11—C16	−177.5 (3)
C7—C1—C2—C3	−167.8 (3)	C15—C10—C11—C16	4.6 (4)
C6—C1—C2—Br1	−173.4 (2)	C10—C11—C12—C13	5.2 (4)
C7—C1—C2—Br1	10.1 (4)	C16—C11—C12—C13	−176.0 (3)
C1—C2—C3—C4	−2.1 (5)	C10—C11—C12—C19	−175.0 (3)
Br1—C2—C3—C4	179.9 (2)	C16—C11—C12—C19	3.8 (4)
C2—C3—C4—C5	−6.9 (5)	C11—C12—C13—C14	−5.7 (4)
C2—C3—C4—C20	171.0 (3)	C19—C12—C13—C14	174.5 (3)
C3—C4—C5—C6	9.1 (5)	C11—C12—C13—C18	175.4 (3)
C20—C4—C5—C6	−168.6 (3)	C19—C12—C13—C18	−4.4 (4)
C3—C4—C5—Br2	−171.9 (2)	C12—C13—C14—C9	−0.4 (4)
C20—C4—C5—Br2	10.3 (4)	C18—C13—C14—C9	178.5 (3)
C4—C5—C6—C1	−2.5 (5)	C12—C13—C14—C17	179.2 (3)
Br2—C5—C6—C1	178.5 (2)	C18—C13—C14—C17	−2.0 (4)
C2—C1—C6—C5	−6.5 (4)	C10—C9—C14—C13	7.0 (4)
C7—C1—C6—C5	170.2 (3)	C8—C9—C14—C13	−174.0 (3)
C6—C1—C7—S1	−46.5 (4)	C10—C9—C14—C17	−172.5 (3)
C2—C1—C7—S1	130.0 (3)	C8—C9—C14—C17	6.4 (4)
S1—C8—C9—C14	66.8 (4)	C11—C12—C19—S2	70.2 (3)
S1—C8—C9—C10	−114.2 (3)	C13—C12—C19—S2	−110.0 (3)
C14—C9—C10—C11	−7.5 (4)	C5—C4—C20—S2	136.9 (3)
C8—C9—C10—C11	173.5 (3)	C3—C4—C20—S2	−40.8 (4)
C14—C9—C10—C15	170.4 (3)	C1—C7—S1—C8	−69.5 (3)
C8—C9—C10—C15	−8.5 (4)	C9—C8—S1—C7	58.3 (3)
C9—C10—C11—C12	1.4 (4)	C4—C20—S2—C19	−71.1 (3)
C15—C10—C11—C12	−176.5 (3)	C12—C19—S2—C20	58.3 (3)