6,14-Dibromo-2,11-dithia-[3.3]paracyclo-phane.

In the title compound, C(16)H(14)Br(2)S(2) [systematic name: 1(2),5(2)-dibromo-2,7-dithia-1,5(1,4)-dibenzenaocta-phane], the cen-troids of the two benzene rings are separated by 3.313 (5) Å. The crystal packing exhibits weak inter-molecular S⋯S contacts of 3.538 (2) Å.

Related literature

For the preparation of the title compound, see: Wang et al. (2003 ▶, 2006 ▶). For a related structure, see: Huang et al. (2010 ▶).

Experimental

Crystal data

C16H14Br2S2

M = 430.21

Orthorhombic,

a = 9.0563 (11) Å

b = 13.8931 (17) Å

c = 24.641 (3) Å

V = 3100.4 (7) Å3

Z = 8

Mo Kα radiation

μ = 5.49 mm−1

T = 298 K

0.26 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.330, T max = 0.610

21950 measured reflections

3372 independent reflections

2150 reflections with I > 2σ(I)

R int = 0.12

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 0.99

3372 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.93 e Å−3

Δρmin = −0.38 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 datablocks I, global. DOI: 10.1107/S1600536810028874/cv2739sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028874/cv2739Isup2.hkl

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

C16H14Br2S2	F(000) = 1696
Mr = 430.21	Dx = 1.839 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5026 reflections
a = 9.0563 (11) Å	θ = 2.8–25.5°
b = 13.8931 (17) Å	µ = 5.49 mm−1
c = 24.641 (3) Å	T = 298 K
V = 3100.4 (7) Å3	Block, colourless
Z = 8	0.26 × 0.20 × 0.10 mm

Bruker SMART APEX diffractometer	3372 independent reflections
Radiation source: fine-focus sealed tube	2150 reflections with I > 2σ(I)
graphite	Rint = 0.12
phi and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→11
Tmin = 0.330, Tmax = 0.610	k = −17→17
21950 measured reflections	l = −31→31

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0521P)2] where P = (Fo2 + 2Fc2)/3
3372 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.93 e Å−3
0 restraints	Δρmin = −0.38 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	−0.01106 (5)	0.31316 (4)	0.233829 (17)	0.05380 (18)
Br2	−0.18330 (6)	0.72155 (4)	0.04515 (2)	0.0638 (2)
C1	−0.0858 (4)	0.4030 (3)	0.13260 (15)	0.0325 (9)
C2	0.0281 (4)	0.3739 (3)	0.16606 (15)	0.0324 (9)
C3	0.1766 (4)	0.3880 (3)	0.15182 (16)	0.0364 (9)
H3	0.2509	0.3694	0.1757	0.044*
C4	0.2127 (4)	0.4289 (3)	0.10301 (17)	0.0364 (9)
C5	0.0981 (4)	0.4501 (3)	0.06696 (15)	0.0397 (10)
H5	0.1197	0.4726	0.0323	0.048*
C6	−0.0453 (4)	0.4379 (3)	0.08239 (15)	0.0366 (9)
H6	−0.1194	0.4540	0.0579	0.044*
C7	0.3717 (4)	0.4516 (3)	0.0900 (2)	0.0507 (11)
H7A	0.4112	0.3984	0.0690	0.061*
H7B	0.4260	0.4536	0.1239	0.061*
C8	0.3707 (5)	0.6542 (3)	0.1030 (2)	0.0527 (12)
H8A	0.4314	0.6433	0.1348	0.063*
H8B	0.3986	0.7160	0.0878	0.063*
C9	0.2122 (4)	0.6589 (3)	0.12027 (16)	0.0380 (10)
C10	0.1679 (4)	0.6251 (3)	0.16986 (17)	0.0420 (10)
H10	0.2385	0.6104	0.1960	0.050*
C11	0.0198 (4)	0.6126 (3)	0.18176 (16)	0.0353 (9)
H11	−0.0071	0.5876	0.2153	0.042*
C12	−0.0886 (4)	0.6365 (3)	0.14498 (15)	0.0342 (9)
C13	−0.0416 (5)	0.6791 (3)	0.09759 (17)	0.0379 (10)
C14	0.1044 (5)	0.6900 (3)	0.08435 (17)	0.0432 (10)
H14	0.1310	0.7181	0.0515	0.052*
C15	−0.2488 (4)	0.6110 (3)	0.15519 (18)	0.0492 (11)
H15A	−0.2963	0.6022	0.1203	0.059*
H15B	−0.2955	0.6659	0.1725	0.059*
C16	−0.2467 (4)	0.4062 (3)	0.15006 (17)	0.0435 (10)
H16A	−0.2715	0.3461	0.1679	0.052*
H16B	−0.3084	0.4120	0.1181	0.052*
S1	0.41002 (13)	0.56115 (8)	0.05360 (5)	0.0539 (3)
S2	−0.28742 (12)	0.50583 (8)	0.19606 (5)	0.0497 (3)

	U11	U22	U33	U12	U13	U23
Br1	0.0655 (3)	0.0599 (3)	0.0360 (3)	−0.0119 (2)	−0.0004 (2)	0.0092 (2)
Br2	0.0722 (4)	0.0703 (4)	0.0490 (3)	0.0220 (3)	−0.0132 (2)	0.0041 (3)
C1	0.034 (2)	0.030 (2)	0.033 (2)	−0.0036 (17)	0.0022 (16)	−0.0072 (17)
C2	0.037 (2)	0.033 (2)	0.0276 (19)	−0.0034 (17)	0.0013 (16)	0.0008 (16)
C3	0.039 (2)	0.032 (2)	0.038 (2)	0.0051 (18)	−0.0051 (18)	−0.0020 (18)
C4	0.035 (2)	0.028 (2)	0.046 (2)	0.0032 (18)	0.0047 (17)	−0.0039 (18)
C5	0.050 (3)	0.039 (2)	0.030 (2)	0.006 (2)	0.0070 (18)	−0.0010 (18)
C6	0.032 (2)	0.043 (2)	0.035 (2)	0.0051 (19)	−0.0032 (17)	−0.0034 (19)
C7	0.034 (2)	0.046 (3)	0.072 (3)	0.004 (2)	0.014 (2)	0.002 (2)
C8	0.040 (3)	0.051 (3)	0.067 (3)	−0.006 (2)	0.016 (2)	−0.010 (2)
C9	0.039 (2)	0.027 (2)	0.047 (2)	−0.0050 (18)	0.0051 (19)	−0.0080 (18)
C10	0.042 (3)	0.041 (2)	0.042 (2)	0.003 (2)	−0.0049 (19)	−0.009 (2)
C11	0.039 (2)	0.036 (2)	0.031 (2)	−0.0020 (18)	0.0074 (17)	−0.0042 (17)
C12	0.036 (2)	0.033 (2)	0.034 (2)	0.0043 (18)	0.0072 (17)	−0.0033 (17)
C13	0.045 (2)	0.031 (2)	0.038 (2)	0.0117 (19)	−0.0023 (18)	−0.0021 (18)
C14	0.055 (3)	0.034 (2)	0.040 (2)	0.002 (2)	0.011 (2)	−0.0012 (19)
C15	0.038 (2)	0.054 (3)	0.056 (3)	0.010 (2)	0.007 (2)	−0.004 (2)
C16	0.033 (2)	0.048 (3)	0.049 (2)	−0.005 (2)	0.002 (2)	−0.006 (2)
S1	0.0477 (7)	0.0482 (7)	0.0658 (8)	−0.0043 (6)	0.0279 (6)	−0.0069 (6)
S2	0.0453 (7)	0.0557 (7)	0.0481 (6)	−0.0039 (6)	0.0205 (5)	−0.0097 (6)

Br1—C2	1.905 (4)	C8—H8A	0.9700
Br2—C13	1.914 (4)	C8—H8B	0.9700
C1—C6	1.379 (5)	C9—C10	1.369 (6)
C1—C2	1.381 (5)	C9—C14	1.387 (6)
C1—C16	1.519 (5)	C10—C11	1.384 (5)
C2—C3	1.403 (5)	C10—H10	0.9300
C3—C4	1.370 (5)	C11—C12	1.377 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.398 (5)	C12—C13	1.377 (5)
C4—C7	1.508 (5)	C12—C15	1.514 (6)
C5—C6	1.364 (5)	C13—C14	1.370 (6)
C5—H5	0.9300	C14—H14	0.9300
C6—H6	0.9300	C15—S2	1.809 (5)
C7—S1	1.800 (4)	C15—H15A	0.9700
C7—H7A	0.9700	C15—H15B	0.9700
C7—H7B	0.9700	C16—S2	1.827 (4)
C8—C9	1.498 (6)	C16—H16A	0.9700
C8—S1	1.811 (4)	C16—H16B	0.9700
C6—C1—C2	116.1 (3)	C10—C9—C8	121.3 (4)
C6—C1—C16	119.9 (4)	C14—C9—C8	120.5 (4)
C2—C1—C16	123.8 (3)	C9—C10—C11	121.1 (4)
C1—C2—C3	121.7 (3)	C9—C10—H10	119.5
C1—C2—Br1	120.9 (3)	C11—C10—H10	119.5
C3—C2—Br1	117.4 (3)	C12—C11—C10	121.4 (4)
C4—C3—C2	120.4 (4)	C12—C11—H11	119.3
C4—C3—H3	119.8	C10—C11—H11	119.3
C2—C3—H3	119.8	C11—C12—C13	116.2 (3)
C3—C4—C5	117.9 (4)	C11—C12—C15	121.2 (4)
C3—C4—C7	120.1 (4)	C13—C12—C15	122.5 (4)
C5—C4—C7	122.0 (4)	C14—C13—C12	123.2 (4)
C6—C5—C4	120.3 (4)	C14—C13—Br2	116.9 (3)
C6—C5—H5	119.9	C12—C13—Br2	119.8 (3)
C4—C5—H5	119.9	C13—C14—C9	119.5 (4)
C5—C6—C1	123.2 (4)	C13—C14—H14	120.2
C5—C6—H6	118.4	C9—C14—H14	120.2
C1—C6—H6	118.4	C12—C15—S2	117.8 (3)
C4—C7—S1	117.8 (3)	C12—C15—H15A	107.9
C4—C7—H7A	107.9	S2—C15—H15A	107.9
S1—C7—H7A	107.9	C12—C15—H15B	107.9
C4—C7—H7B	107.9	S2—C15—H15B	107.9
S1—C7—H7B	107.9	H15A—C15—H15B	107.2
H7A—C7—H7B	107.2	C1—C16—S2	113.0 (3)
C9—C8—S1	114.2 (3)	C1—C16—H16A	109.0
C9—C8—H8A	108.7	S2—C16—H16A	109.0
S1—C8—H8A	108.7	C1—C16—H16B	109.0
C9—C8—H8B	108.7	S2—C16—H16B	109.0
S1—C8—H8B	108.7	H16A—C16—H16B	107.8
H8A—C8—H8B	107.6	C7—S1—C8	103.3 (2)
C10—C9—C14	118.0 (4)	C15—S2—C16	103.2 (2)
C6—C1—C2—C3	6.1 (5)	C9—C10—C11—C12	−2.1 (6)
C16—C1—C2—C3	−168.6 (4)	C10—C11—C12—C13	−4.2 (6)
C6—C1—C2—Br1	−174.1 (3)	C10—C11—C12—C15	172.1 (4)
C16—C1—C2—Br1	11.2 (5)	C11—C12—C13—C14	6.0 (6)
C1—C2—C3—C4	−1.9 (6)	C15—C12—C13—C14	−170.3 (4)
Br1—C2—C3—C4	178.3 (3)	C11—C12—C13—Br2	−176.7 (3)
C2—C3—C4—C5	−4.0 (6)	C15—C12—C13—Br2	7.0 (5)
C2—C3—C4—C7	174.8 (4)	C12—C13—C14—C9	−1.4 (6)
C3—C4—C5—C6	5.7 (6)	Br2—C13—C14—C9	−178.8 (3)
C7—C4—C5—C6	−173.1 (4)	C10—C9—C14—C13	−5.1 (6)
C4—C5—C6—C1	−1.4 (6)	C8—C9—C14—C13	169.4 (4)
C2—C1—C6—C5	−4.4 (5)	C11—C12—C15—S2	−28.6 (5)
C16—C1—C6—C5	170.4 (4)	C13—C12—C15—S2	147.5 (3)
C3—C4—C7—S1	−141.7 (3)	C6—C1—C16—S2	−100.7 (4)
C5—C4—C7—S1	37.1 (5)	C2—C1—C16—S2	73.7 (5)
S1—C8—C9—C10	104.9 (4)	C4—C7—S1—C8	70.3 (4)
S1—C8—C9—C14	−69.4 (5)	C9—C8—S1—C7	−64.4 (4)
C14—C9—C10—C11	6.8 (6)	C12—C15—S2—C16	−74.8 (3)
C8—C9—C10—C11	−167.6 (4)	C1—C16—S2—C15	62.9 (3)