4,5,4',5'-Tetrakis(2-methyl-thio­phen-3-yl)-[2,2']­bi­[[1,3]­di­thiol­yl­idene]

The structure of the title compound, C₂₆H₂₀S₈, has been established by X-ray crystallography. In space group C2/c, the asymmetric unit contains one mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.072
• wR factor = 0.138
• Data-to-parameter ratio = 11.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



THETM_01  Alert B The value of sine(theta_max)/wavelength is less than 0.575
          Calculated sin(theta_max)/wavelength =    0.5606


 Alert Level C:



CELLV_02  Alert C The supplied cell volume s.u. differs from that
          calculated from the cell parameter s.u.'s by > 2
          Calculated cell volume su =       8.23
          Cell volume su given      =       6.00

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           23.48
         From the CIF: _reflns_number_total               3519
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         3849
         Completeness (_total/calc)             91.43%
          Alert C: < 95% complete

RINTA_01  Alert C The value of Rint is greater than 0.10
          Rint given   0.117


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 3 Alert Level C = Please check

---

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b).

(I)

Crystal data

C26H20S8	F(000) = 2432
Mr = 588.90	Dx = 1.502 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 27.083 (2) Å	Cell parameters from 11446 reflections
b = 10.0911 (10) Å	θ = 2.9–23.5°
c = 20.304 (2) Å	µ = 0.70 mm^−1
β = 110.212 (3)°	T = 150 K
V = 5207.5 (6) Å^3	Needle cut from platelet, colourless
Z = 8	0.12 × 0.02 × 0.01 mm

Data collection

Nonius KappaCCD area detector diffractometer	3519 independent reflections
Radiation source: Nonius FR591 rotating anode	1961 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.117
φ and ω scans to fill Ewald sphere	θmax = 23.5°, θmin = 3.0°
Absorption correction: multi-scan (Blessing, 1997)	h = −29→25
Tmin = 0.921, Tmax = 0.997	k = −8→11
11126 measured reflections	l = −21→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0436P)^2] where P = (Fo^2 + 2Fc^2)/3
3519 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.30600 (8)	0.67096 (15)	0.49123 (8)	0.0415 (5)
S2	0.37273 (8)	0.43550 (15)	0.53456 (8)	0.0439 (5)
S3	0.42453 (8)	1.06705 (15)	0.58309 (9)	0.0518 (6)
S4	0.56078 (8)	0.62729 (17)	0.60839 (9)	0.0563 (6)
C1	0.3113 (3)	0.4987 (6)	0.4825 (3)	0.0386 (17)
C2	0.3734 (3)	0.6987 (6)	0.5289 (3)	0.0372 (18)
C3	0.4044 (3)	0.5905 (6)	0.5481 (3)	0.0404 (19)
C4	0.4177 (3)	0.9012 (6)	0.5965 (3)	0.0430 (19)
C5	0.3893 (3)	0.8382 (6)	0.5358 (3)	0.0402 (18)
C6	0.3743 (3)	0.9290 (6)	0.4782 (3)	0.0445 (19)
H6	0.3544	0.9030	0.4315	0.053*
C7	0.3905 (3)	1.0539 (7)	0.4956 (3)	0.050 (2)
H7	0.3839	1.1255	0.4634	0.060*
C8	0.4396 (3)	0.8443 (6)	0.6688 (3)	0.059 (2)
H8A	0.4576	0.9141	0.7019	0.089*
H8B	0.4646	0.7737	0.6696	0.089*
H8C	0.4109	0.8079	0.6822	0.089*
C9	0.4963 (3)	0.6469 (6)	0.5535 (3)	0.0421 (18)
C10	0.4625 (3)	0.5907 (5)	0.5810 (3)	0.0371 (18)
C11	0.4895 (3)	0.5294 (6)	0.6481 (4)	0.050 (2)
H11	0.4721	0.4838	0.6747	0.060*
C12	0.5412 (4)	0.5434 (6)	0.6684 (4)	0.060 (2)
H12	0.5648	0.5105	0.7117	0.07 (2)*
C13	0.4835 (3)	0.7158 (6)	0.4841 (3)	0.055 (2)
H13A	0.5161	0.7457	0.4781	0.082*
H13B	0.4609	0.7924	0.4826	0.082*
H13C	0.4651	0.6542	0.4462	0.082*
S1'	0.21151 (8)	0.49490 (15)	0.38943 (9)	0.0447 (5)
S2'	0.27636 (8)	0.25545 (14)	0.42608 (8)	0.0442 (5)
S3'	0.06403 (9)	0.44801 (17)	0.16707 (9)	0.0550 (6)
S4'	0.18921 (8)	−0.08128 (16)	0.23317 (9)	0.0533 (6)
C1'	0.2727 (3)	0.4263 (6)	0.4383 (3)	0.0425 (19)
C2'	0.1891 (3)	0.3565 (6)	0.3331 (3)	0.0403 (19)
C3'	0.2196 (3)	0.2470 (6)	0.3511 (3)	0.0411 (18)
C4'	0.1274 (3)	0.4661 (6)	0.2253 (3)	0.043 (2)
C5'	0.1381 (3)	0.3716 (6)	0.2758 (3)	0.0400 (19)
C6'	0.0935 (3)	0.2866 (7)	0.2663 (4)	0.053 (2)
H6'	0.0935	0.2149	0.2966	0.064*
C7'	0.0517 (3)	0.3203 (6)	0.2094 (3)	0.052 (2)
H7'	0.0188	0.2753	0.1955	0.062*
C8'	0.1624 (3)	0.5667 (6)	0.2116 (4)	0.065 (2)
H8'1	0.1423	0.6207	0.1711	0.098*
H8'2	0.1913	0.5223	0.2017	0.098*
H8'3	0.1769	0.6237	0.2529	0.098*
C9'	0.1937 (3)	0.0877 (6)	0.2472 (4)	0.050 (2)
C10'	0.2098 (3)	0.1138 (6)	0.3174 (3)	0.0409 (19)
C11'	0.2192 (3)	−0.0040 (6)	0.3592 (4)	0.050 (2)
H11'	0.2321	−0.0030	0.4091	0.060*
C12'	0.2079 (3)	−0.1163 (7)	0.3212 (4)	0.061 (2)
H12'	0.2100	−0.2029	0.3404	0.073*
C13'	0.1810 (3)	0.1787 (6)	0.1863 (3)	0.056 (2)
H13D	0.1702	0.1270	0.1428	0.084*
H13E	0.2122	0.2315	0.1896	0.084*
H13F	0.1523	0.2379	0.1862	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0423 (15)	0.0463 (10)	0.0335 (11)	0.0032 (9)	0.0100 (10)	−0.0030 (7)
S2	0.0469 (15)	0.0461 (10)	0.0348 (11)	0.0038 (9)	0.0089 (9)	0.0002 (8)
S3	0.0554 (16)	0.0488 (11)	0.0452 (12)	−0.0025 (10)	0.0099 (10)	−0.0084 (9)
S4	0.0460 (16)	0.0726 (13)	0.0467 (13)	0.0028 (11)	0.0115 (11)	0.0059 (9)
C1	0.034 (5)	0.057 (4)	0.024 (4)	−0.007 (4)	0.009 (4)	−0.006 (3)
C2	0.047 (6)	0.044 (4)	0.023 (4)	0.017 (4)	0.015 (4)	0.002 (3)
C3	0.052 (6)	0.046 (4)	0.025 (4)	0.009 (4)	0.015 (4)	−0.003 (3)
C4	0.045 (6)	0.057 (4)	0.023 (4)	0.002 (4)	0.007 (4)	−0.009 (3)
C5	0.039 (5)	0.043 (4)	0.036 (5)	−0.002 (4)	0.009 (4)	−0.006 (4)
C6	0.055 (6)	0.037 (4)	0.038 (4)	0.009 (4)	0.012 (4)	−0.001 (4)
C7	0.045 (6)	0.063 (5)	0.036 (5)	0.011 (4)	0.007 (4)	0.009 (3)
C8	0.082 (7)	0.065 (5)	0.029 (5)	−0.001 (4)	0.016 (4)	−0.013 (3)
C9	0.043 (6)	0.044 (4)	0.040 (5)	0.002 (4)	0.016 (4)	−0.004 (3)
C10	0.037 (6)	0.044 (4)	0.022 (4)	0.000 (4)	0.000 (4)	−0.003 (3)
C11	0.042 (7)	0.066 (5)	0.041 (5)	−0.006 (4)	0.014 (4)	0.006 (4)
C12	0.061 (8)	0.079 (5)	0.031 (5)	−0.004 (5)	0.005 (5)	0.009 (4)
C13	0.053 (6)	0.068 (5)	0.048 (5)	0.011 (4)	0.024 (4)	0.011 (4)
S1'	0.0451 (15)	0.0436 (10)	0.0375 (11)	0.0005 (9)	0.0043 (10)	−0.0055 (8)
S2'	0.0524 (15)	0.0438 (10)	0.0319 (11)	0.0040 (9)	0.0090 (10)	0.0011 (8)
S3'	0.0523 (17)	0.0654 (12)	0.0395 (12)	0.0034 (10)	0.0059 (10)	−0.0060 (9)
S4'	0.0601 (17)	0.0509 (11)	0.0438 (12)	0.0020 (10)	0.0116 (11)	−0.0088 (8)
C1'	0.058 (6)	0.048 (4)	0.022 (4)	0.003 (4)	0.014 (4)	0.007 (3)
C2'	0.051 (6)	0.047 (4)	0.021 (4)	0.005 (4)	0.010 (4)	0.010 (3)
C3'	0.048 (6)	0.050 (4)	0.023 (4)	−0.010 (4)	0.009 (4)	0.006 (3)
C4'	0.055 (6)	0.034 (4)	0.039 (5)	0.003 (4)	0.014 (4)	−0.006 (3)
C5'	0.056 (6)	0.036 (4)	0.029 (4)	0.007 (4)	0.016 (4)	−0.003 (3)
C6'	0.060 (7)	0.059 (5)	0.044 (5)	−0.008 (5)	0.023 (5)	−0.011 (4)
C7'	0.031 (6)	0.081 (5)	0.033 (5)	−0.010 (4)	−0.002 (4)	−0.020 (4)
C8'	0.081 (7)	0.052 (4)	0.054 (5)	−0.003 (5)	0.013 (5)	−0.001 (4)
C9'	0.052 (6)	0.065 (5)	0.039 (5)	0.003 (4)	0.021 (4)	−0.004 (4)
C10'	0.043 (6)	0.044 (4)	0.041 (5)	0.002 (3)	0.023 (4)	−0.002 (4)
C11'	0.062 (6)	0.044 (4)	0.043 (5)	−0.003 (4)	0.017 (4)	−0.002 (4)
C12'	0.080 (8)	0.046 (4)	0.066 (6)	−0.004 (4)	0.036 (5)	−0.002 (4)
C13'	0.087 (7)	0.054 (4)	0.036 (4)	0.003 (4)	0.034 (4)	0.001 (4)

Geometric parameters (Å, º)

S1—C2	1.741 (7)	S1'—C1'	1.753 (7)
S1—C1	1.758 (6)	S1'—C2'	1.774 (6)
S2—C1	1.755 (7)	S2'—C1'	1.749 (6)
S2—C3	1.759 (7)	S2'—C3'	1.753 (7)
S3—C7	1.700 (7)	S3'—C7'	1.647 (7)
S3—C4	1.716 (6)	S3'—C4'	1.726 (7)
S4—C12	1.713 (7)	S4'—C12'	1.717 (7)
S4—C9	1.727 (7)	S4'—C9'	1.726 (6)
C1—C1'	1.336 (9)	C2'—C3'	1.351 (8)
C2—C3	1.349 (8)	C2'—C5'	1.475 (10)
C2—C5	1.465 (8)	C3'—C10'	1.490 (8)
C3—C10	1.482 (10)	C4'—C5'	1.356 (8)
C4—C5	1.363 (8)	C4'—C8'	1.479 (9)
C4—C8	1.495 (8)	C5'—C6'	1.440 (9)
C5—C6	1.430 (8)	C6'—C7'	1.352 (9)
C6—C7	1.342 (8)	C6'—H6'	0.950
C6—H6	0.950	C7'—H7'	0.950
C7—H7	0.950	C8'—H8'1	0.980
C8—H8A	0.980	C8'—H8'2	0.980
C8—H8B	0.980	C8'—H8'3	0.980
C8—H8C	0.980	C9'—C10'	1.365 (8)
C9—C10	1.352 (9)	C9'—C13'	1.482 (8)
C9—C13	1.501 (8)	C10'—C11'	1.432 (8)
C10—C11	1.444 (9)	C11'—C12'	1.346 (8)
C11—C12	1.322 (9)	C11'—H11'	0.950
C11—H11	0.950	C12'—H12'	0.950
C12—H12	0.950	C13'—H13D	0.980
C13—H13A	0.980	C13'—H13E	0.980
C13—H13B	0.980	C13'—H13F	0.980
C13—H13C	0.980
C2—S1—C1	95.4 (3)	C1'—S1'—C2'	95.7 (3)
C1—S2—C3	94.6 (3)	C1'—S2'—C3'	95.5 (3)
C7—S3—C4	92.3 (3)	C7'—S3'—C4'	93.4 (4)
C12—S4—C9	91.3 (4)	C12'—S4'—C9'	93.1 (3)
C1'—C1—S2	124.4 (5)	C1—C1'—S2'	124.4 (6)
C1'—C1—S1	122.5 (6)	C1—C1'—S1'	122.1 (5)
S2—C1—S1	113.1 (4)	S2'—C1'—S1'	113.5 (4)
C3—C2—C5	128.1 (7)	C3'—C2'—C5'	128.0 (6)
C3—C2—S1	116.7 (5)	C3'—C2'—S1'	115.4 (5)
C5—C2—S1	115.2 (5)	C5'—C2'—S1'	116.5 (5)
C2—C3—C10	125.9 (6)	C2'—C3'—C10'	128.2 (6)
C2—C3—S2	117.0 (6)	C2'—C3'—S2'	117.7 (5)
C10—C3—S2	117.1 (5)	C10'—C3'—S2'	114.0 (5)
C5—C4—C8	128.1 (6)	C5'—C4'—C8'	129.9 (7)
C5—C4—S3	111.7 (5)	C5'—C4'—S3'	110.2 (5)
C8—C4—S3	120.1 (5)	C8'—C4'—S3'	119.6 (5)
C4—C5—C6	110.7 (5)	C4'—C5'—C6'	111.6 (7)
C4—C5—C2	126.1 (6)	C4'—C5'—C2'	124.5 (7)
C6—C5—C2	123.1 (6)	C6'—C5'—C2'	123.9 (6)
C7—C6—C5	114.2 (6)	C7'—C6'—C5'	112.4 (6)
C7—C6—H6	122.9	C7'—C6'—H6'	123.8
C5—C6—H6	122.9	C5'—C6'—H6'	123.8
C6—C7—S3	111.1 (5)	C6'—C7'—S3'	112.4 (6)
C6—C7—H7	124.5	C6'—C7'—H7'	123.8
S3—C7—H7	124.5	S3'—C7'—H7'	123.8
C4—C8—H8A	109.5	C4'—C8'—H8'1	109.5
C4—C8—H8B	109.5	C4'—C8'—H8'2	109.5
H8A—C8—H8B	109.5	H8'1—C8'—H8'2	109.5
C4—C8—H8C	109.5	C4'—C8'—H8'3	109.5
H8A—C8—H8C	109.5	H8'1—C8'—H8'3	109.5
H8B—C8—H8C	109.5	H8'2—C8'—H8'3	109.5
C10—C9—C13	127.7 (7)	C10'—C9'—C13'	130.5 (6)
C10—C9—S4	111.4 (5)	C10'—C9'—S4'	110.0 (5)
C13—C9—S4	120.9 (5)	C13'—C9'—S4'	119.5 (5)
C9—C10—C11	111.9 (7)	C9'—C10'—C11'	112.7 (5)
C9—C10—C3	125.5 (6)	C9'—C10'—C3'	126.6 (5)
C11—C10—C3	122.6 (7)	C11'—C10'—C3'	120.6 (6)
C12—C11—C10	112.7 (7)	C12'—C11'—C10'	113.6 (6)
C12—C11—H11	123.6	C12'—C11'—H11'	123.2
C10—C11—H11	123.6	C10'—C11'—H11'	123.2
C11—C12—S4	112.6 (6)	C11'—C12'—S4'	110.5 (5)
C11—C12—H12	123.7	C11'—C12'—H12'	124.7
S4—C12—H12	123.7	S4'—C12'—H12'	124.7
C9—C13—H13A	109.5	C9'—C13'—H13D	109.5
C9—C13—H13B	109.5	C9'—C13'—H13E	109.5
H13A—C13—H13B	109.5	H13D—C13'—H13E	109.5
C9—C13—H13C	109.5	C9'—C13'—H13F	109.5
H13A—C13—H13C	109.5	H13D—C13'—H13F	109.5
H13B—C13—H13C	109.5	H13E—C13'—H13F	109.5
S1—C1—C1'—S1'	−4.5 (8)	S1'—C2'—C5'—C4'	58.7 (8)
S2—C1—C1'—S2'	1.3 (9)	S2—C3—C10—C9	124.2 (6)
S1—C2—C5—C4	123.1 (7)	S2'—C3'—C10'—C9'	−137.8 (7)