2,2'-(1,4-Phenyl-ene)bis-(propane-2,2-di-yl) bis-(benzodi-thio-ate).

The title compound, C26H26S4, shows a dihedral angle of 76.64 (15)° between the central and peripheral benzene rings. An inversion center is located at the centroid of the thio-benzoyl ring. In the crystal, weak C-H⋯S inter-actions form C(5) chains along [001]. There are no classical hydrogen bonds.

Related literature

For control of the behavior of polymerization reactions, see: Patton et al. (2005 ▶); You et al. (2007 ▶); Pafiti et al. (2010 ▶). For radical polymerization with RAFT reactions, see: Le et al. (1998 ▶). For telechelic polymers, see: Tasdelen et al. (2011 ▶); Goethals (1989 ▶). For hydrogen bonding, see: Nardelli (1995 ▶). For graph-set motifs, see: Etter (1990 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C26H26S4

M = 466.75

Monoclinic,

a = 8.6981 (6) Å

b = 11.7074 (7) Å

c = 12.5612 (6) Å

β = 107.626 (4)°

V = 1219.08 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.40 mm−1

T = 295 K

0.41 × 0.29 × 0.16 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.874, T max = 0.939

4051 measured reflections

2160 independent reflections

1775 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.091

S = 1.03

2160 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.22 e Å−3

Data collection: COLLECT (Hooft, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681303465X/kj2235sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681303465X/kj2235Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681303465X/kj2235Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C26H26S4	Z = 2
Mr = 466.75	F(000) = 492
Monoclinic, P21/c	Dx = 1.272 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.6981 (6) Å	Cell parameters from 4051 reflections
b = 11.7074 (7) Å	µ = 0.40 mm−1
c = 12.5612 (6) Å	T = 295 K
β = 107.626 (4)°	Block, pink
V = 1219.08 (13) Å3	0.41 × 0.29 × 0.16 mm

Bruker–Nonius KappaCCD diffractometer	2160 independent reflections
Radiation source: fine-focus sealed tube	1775 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
CCD rotation images, thick slices scans	θmax = 25.1°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −10→10
Tmin = 0.874, Tmax = 0.939	k = −12→13
4051 measured reflections	l = −14→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.3633P] where P = (Fo2 + 2Fc2)/3
2160 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.19 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
S1	0.50091 (6)	0.16376 (4)	0.06933 (4)	0.04958 (17)
S2	0.75578 (8)	0.23202 (6)	−0.03441 (5)	0.0685 (2)
C1	0.9423 (3)	0.0464 (2)	0.13247 (19)	0.0610 (6)
H1	0.9617	0.0565	0.0642	0.073*
C2	1.0454 (3)	−0.0191 (2)	0.2131 (2)	0.0754 (7)
H2	1.1332	−0.0541	0.1990	0.090*
C3	1.0198 (3)	−0.0335 (2)	0.3155 (2)	0.0754 (7)
H3	1.0904	−0.0778	0.3704	0.091*
C4	0.8906 (3)	0.0175 (2)	0.33591 (18)	0.0644 (6)
H4	0.8736	0.0081	0.4050	0.077*
C5	0.7852 (3)	0.08278 (17)	0.25504 (16)	0.0526 (5)
H5	0.6975	0.1171	0.2699	0.063*
C6	0.8086 (2)	0.09805 (15)	0.15112 (16)	0.0456 (4)
C7	0.6960 (2)	0.16592 (15)	0.06088 (16)	0.0462 (5)
C8	0.3740 (2)	0.26543 (15)	−0.03377 (16)	0.0462 (4)
C9	0.3421 (3)	0.21941 (19)	−0.15129 (18)	0.0668 (6)
H9A	0.2986	0.1436	−0.1554	0.100*
H9B	0.4413	0.2174	−0.1699	0.100*
H9C	0.2663	0.2681	−0.2030	0.100*
C10	0.2164 (3)	0.26165 (19)	−0.0017 (2)	0.0628 (6)
H10A	0.2361	0.2906	0.0727	0.094*
H10B	0.1789	0.1842	−0.0050	0.094*
H10C	0.1360	0.3078	−0.0529	0.094*
C11	0.4441 (2)	0.38607 (15)	−0.01603 (14)	0.0388 (4)
C12	0.4914 (2)	0.43533 (16)	0.08868 (15)	0.0446 (4)
H12	0.4861	0.3926	0.1499	0.054*
C13	0.4535 (2)	0.45299 (16)	−0.10490 (15)	0.0439 (4)
H13	0.4222	0.4225	−0.1766	0.053*

	U11	U22	U33	U12	U13	U23
S1	0.0527 (3)	0.0368 (3)	0.0662 (3)	0.0003 (2)	0.0284 (2)	0.0081 (2)
S2	0.0734 (4)	0.0679 (4)	0.0797 (4)	0.0051 (3)	0.0461 (3)	0.0187 (3)
C1	0.0580 (13)	0.0617 (13)	0.0683 (13)	0.0053 (11)	0.0264 (11)	−0.0067 (11)
C2	0.0560 (14)	0.0766 (17)	0.0882 (18)	0.0152 (12)	0.0138 (13)	−0.0131 (14)
C3	0.0697 (16)	0.0678 (16)	0.0714 (16)	0.0058 (13)	−0.0046 (13)	−0.0023 (13)
C4	0.0687 (15)	0.0667 (14)	0.0507 (12)	−0.0063 (12)	0.0077 (11)	−0.0045 (11)
C5	0.0566 (12)	0.0493 (11)	0.0532 (11)	−0.0037 (9)	0.0186 (10)	−0.0082 (9)
C6	0.0502 (10)	0.0342 (9)	0.0551 (11)	−0.0045 (8)	0.0200 (9)	−0.0074 (8)
C7	0.0551 (11)	0.0340 (9)	0.0564 (11)	−0.0011 (8)	0.0270 (9)	−0.0042 (8)
C8	0.0493 (11)	0.0349 (9)	0.0540 (11)	−0.0059 (8)	0.0150 (9)	−0.0007 (8)
C9	0.0871 (17)	0.0466 (12)	0.0601 (13)	−0.0201 (12)	0.0124 (12)	−0.0129 (10)
C10	0.0485 (12)	0.0508 (12)	0.0889 (16)	−0.0078 (9)	0.0207 (12)	0.0033 (11)
C11	0.0379 (9)	0.0333 (9)	0.0461 (10)	−0.0006 (7)	0.0140 (8)	−0.0014 (8)
C12	0.0551 (11)	0.0391 (10)	0.0414 (10)	−0.0035 (9)	0.0171 (8)	0.0040 (8)
C13	0.0524 (11)	0.0396 (10)	0.0391 (9)	−0.0037 (8)	0.0129 (8)	−0.0040 (8)

S1—C7	1.7325 (19)	C8—C9	1.516 (3)
S1—C8	1.857 (2)	C8—C11	1.528 (2)
S2—C7	1.6366 (19)	C8—C10	1.541 (3)
C1—C2	1.367 (3)	C9—H9A	0.9600
C1—C6	1.393 (3)	C9—H9B	0.9600
C1—H1	0.9300	C9—H9C	0.9600
C2—C3	1.380 (4)	C10—H10A	0.9600
C2—H2	0.9300	C10—H10B	0.9600
C3—C4	1.364 (3)	C10—H10C	0.9600
C3—H3	0.9300	C11—C12	1.380 (2)
C4—C5	1.376 (3)	C11—C13	1.386 (2)
C4—H4	0.9300	C12—C13i	1.386 (3)
C5—C6	1.392 (3)	C12—H12	0.9300
C5—H5	0.9300	C13—C12i	1.386 (3)
C6—C7	1.484 (3)	C13—H13	0.9300
C7—S1—C8	109.55 (9)	C9—C8—S1	110.25 (14)
C2—C1—C6	120.9 (2)	C11—C8—S1	111.34 (13)
C2—C1—H1	119.6	C10—C8—S1	100.81 (13)
C6—C1—H1	119.6	C8—C9—H9A	109.5
C1—C2—C3	120.3 (2)	C8—C9—H9B	109.5
C1—C2—H2	119.9	H9A—C9—H9B	109.5
C3—C2—H2	119.9	C8—C9—H9C	109.5
C4—C3—C2	119.8 (2)	H9A—C9—H9C	109.5
C4—C3—H3	120.1	H9B—C9—H9C	109.5
C2—C3—H3	120.1	C8—C10—H10A	109.5
C3—C4—C5	120.5 (2)	C8—C10—H10B	109.5
C3—C4—H4	119.8	H10A—C10—H10B	109.5
C5—C4—H4	119.8	C8—C10—H10C	109.5
C4—C5—C6	120.7 (2)	H10A—C10—H10C	109.5
C4—C5—H5	119.7	H10B—C10—H10C	109.5
C6—C5—H5	119.7	C12—C11—C13	117.27 (16)
C5—C6—C1	117.94 (19)	C12—C11—C8	121.06 (16)
C5—C6—C7	122.36 (17)	C13—C11—C8	121.55 (16)
C1—C6—C7	119.70 (18)	C11—C12—C13i	121.62 (16)
C6—C7—S2	121.99 (14)	C11—C12—H12	119.2
C6—C7—S1	112.15 (13)	C13i—C12—H12	119.2
S2—C7—S1	125.85 (13)	C11—C13—C12i	121.12 (17)
C9—C8—C11	114.68 (16)	C11—C13—H13	119.4
C9—C8—C10	109.22 (18)	C12i—C13—H13	119.4
C11—C8—C10	109.63 (16)
C6—C1—C2—C3	−1.1 (4)	C7—S1—C8—C9	71.76 (16)
C1—C2—C3—C4	0.3 (4)	C7—S1—C8—C11	−56.71 (15)
C2—C3—C4—C5	0.3 (4)	C7—S1—C8—C10	−172.92 (13)
C3—C4—C5—C6	−0.1 (3)	C9—C8—C11—C12	−174.69 (18)
C4—C5—C6—C1	−0.7 (3)	C10—C8—C11—C12	62.0 (2)
C4—C5—C6—C7	178.79 (18)	S1—C8—C11—C12	−48.6 (2)
C2—C1—C6—C5	1.2 (3)	C9—C8—C11—C13	9.4 (3)
C2—C1—C6—C7	−178.2 (2)	C10—C8—C11—C13	−113.8 (2)
C5—C6—C7—S2	151.88 (16)	S1—C8—C11—C13	135.50 (16)
C1—C6—C7—S2	−28.7 (3)	C13—C11—C12—C13i	−0.2 (3)
C5—C6—C7—S1	−28.9 (2)	C8—C11—C12—C13i	−176.23 (17)
C1—C6—C7—S1	150.59 (16)	C12—C11—C13—C12i	0.2 (3)
C8—S1—C7—C6	172.46 (12)	C8—C11—C13—C12i	176.21 (17)
C8—S1—C7—S2	−8.33 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···S2ii	0.93	2.94	3.489 (2)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯S2i	0.93	2.94	3.489 (2)	119

Symmetry code: (i) .