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The asymmetric unit of the title compound, C18H10O2S4, contains one half-mol­ecule, the other half being generated by a twofold rotation axis. The compound was synthesized in good yield utilizing a benzoin condensation reaction (starting with 2,2'-bithienyl-5-carbaldehyde). The thiophene rings are not coplanar; the central C-C-C-C torsion angle is -138.62 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042139/ez2038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042139/ez2038Isup2.hkl
Contains datablock I

CCDC reference: 627641

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.039
  • wR factor = 0.103
  • Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT301_ALERT_3_B Main Residue Disorder ......................... 29.00 Perc.
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. O7 .. 2.69 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1998); software used to prepare material for publication: enCIFer (Allen et al., 2004).

1,2-Bis(2,2'-bithienyl-5-yl)ethane-1,2-dione top
Crystal data top
C18H10O2S4F(000) = 792
Mr = 386.50Dx = 1.608 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C_2ycCell parameters from 1906 reflections
a = 20.724 (4) Åθ = 2.7–25.4°
b = 3.8630 (8) ŵ = 0.60 mm1
c = 21.472 (4) ÅT = 100 K
β = 111.72 (3)°Block, orange
V = 1596.9 (6) Å30.53 × 0.04 × 0.03 mm
Z = 4
Data collection top
Oxford Diffraction Gemini R CCD
diffractometer
1401 independent reflections
Radiation source: fine-focus sealed tube1035 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ω and φ scansθmax = 25.0°, θmin = 4.0°
Absorption correction: analytical
(Clark & Reid, 1995)
h = 2424
Tmin = 0.921, Tmax = 0.987k = 44
3569 measured reflectionsl = 2523
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.0524P)2]
where P = (Fo2 + 2Fc2)/3
1401 reflections(Δ/σ)max < 0.001
129 parametersΔρmax = 0.35 e Å3
253 restraintsΔρmin = 0.29 e Å3
Special details top

Experimental. face-indexed (CrysAlis RED; Oxford Diffraction, 2006)

1H NMR (CDCl3): δ 8.03 (d, 1H, H-4, J4,3 = 4.15 Hz), 7.41 (dd, 1 H, H-3', J3',4' = 3.68 Hz, J3',5' = 0.95 Hz), 7.38 (dd, 1H, H-5', J5',4'= 5.1 Hz, J5',3' = 0.95 Hz), 7.25(d, 1H, H-4, J4,3 = 4.15 Hz), 7.09 (dd, 1H, H-4', J4',3' = 3.68 Hz, J4',5' = 5.1 Hz). 13C NMR (CDCl3): δ 181.31 (CO), 149.73 (C), 138.41 (CH), 136.10 (C), 134.11 (C), 128.45 (CH), 127.37 (CH), 126.38 (CH), 124.70 (CH). IR (KBr, v, cm-1): 3101 (w), 1628 (s), 1441 (s), 1230 (s), 1051 (s), 1047 (s), 796 (s), 692 (s). UV (methanol) λmax 399 nm (log ε = 4.777).

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.15888 (4)0.03845 (19)0.37792 (3)0.0187 (3)
C20.22203 (14)0.1446 (7)0.35420 (12)0.0176 (6)
C30.19325 (14)0.2689 (7)0.28831 (12)0.0189 (6)
H30.21950.38290.26630.029 (4)*
C40.12220 (15)0.2077 (7)0.25854 (14)0.0184 (6)
H40.09460.27460.21400.029 (4)*
C50.09678 (12)0.0410 (7)0.30043 (13)0.0178 (6)
C60.02422 (12)0.0828 (7)0.28676 (13)0.0180 (6)
O70.00656 (10)0.2043 (5)0.32978 (9)0.0255 (5)
C8B0.29370 (14)0.1591 (7)0.39993 (14)0.0198 (6)0.291 (4)
C12B0.3442 (8)0.273 (6)0.3802 (11)0.0242 (15)0.291 (4)
H12B0.33950.35970.33730.029 (4)*0.291 (4)
S9B0.3195 (7)0.063 (3)0.4759 (5)0.0239 (11)0.291 (4)
C10B0.39655 (16)0.1080 (8)0.49557 (16)0.0307 (7)0.291 (4)
H10B0.42820.05240.53930.029 (4)*0.291 (4)
C11B0.41834 (16)0.2304 (9)0.44841 (17)0.0309 (7)0.291 (4)
H11B0.46450.28120.45230.029 (4)*0.291 (4)
C8A0.29370 (14)0.1591 (7)0.39993 (14)0.0198 (6)0.709 (4)
C12A0.3201 (11)0.036 (5)0.4695 (9)0.0229 (14)0.709 (4)
H12A0.29420.06820.49300.029 (4)*0.709 (4)
S9A0.35869 (8)0.2927 (6)0.37567 (10)0.0197 (4)0.709 (4)
C10A0.41834 (16)0.2304 (9)0.44841 (17)0.0309 (7)0.709 (4)
H10A0.46590.27750.45720.029 (4)*0.709 (4)
C11A0.39655 (16)0.1080 (8)0.49557 (16)0.0307 (7)0.709 (4)
H11A0.42640.07100.54080.029 (4)*0.709 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0182 (4)0.0229 (5)0.0151 (4)0.0007 (3)0.0062 (3)0.0005 (3)
C20.0204 (12)0.0159 (14)0.0184 (13)0.0002 (11)0.0094 (10)0.0036 (11)
C30.0223 (13)0.0190 (15)0.0181 (14)0.0013 (13)0.0106 (11)0.0025 (12)
C40.0232 (14)0.0182 (15)0.0147 (13)0.0031 (13)0.0079 (11)0.0010 (12)
C50.0211 (13)0.0191 (14)0.0140 (13)0.0044 (12)0.0075 (11)0.0010 (11)
C60.0190 (14)0.0195 (15)0.0172 (14)0.0014 (12)0.0087 (12)0.0003 (12)
O70.0219 (11)0.0353 (13)0.0208 (11)0.0019 (10)0.0095 (9)0.0061 (10)
C8B0.0190 (11)0.0192 (12)0.0210 (12)0.0002 (10)0.0072 (9)0.0037 (10)
C12B0.021 (2)0.025 (2)0.026 (2)0.001 (2)0.007 (2)0.004 (2)
S9B0.0223 (14)0.027 (2)0.0181 (19)0.0036 (15)0.0028 (15)0.0014 (16)
C10B0.0270 (12)0.0320 (14)0.0250 (13)0.0062 (12)0.0001 (11)0.0063 (12)
C11B0.0224 (12)0.0305 (14)0.0381 (14)0.0011 (12)0.0091 (11)0.0092 (12)
C8A0.0190 (11)0.0192 (12)0.0210 (12)0.0002 (10)0.0072 (9)0.0037 (10)
C12A0.0209 (19)0.027 (2)0.020 (2)0.003 (2)0.0065 (19)0.004 (2)
S9A0.0165 (8)0.0245 (7)0.0198 (7)0.0027 (6)0.0088 (5)0.0011 (5)
C10A0.0224 (12)0.0305 (14)0.0381 (14)0.0011 (12)0.0091 (11)0.0092 (12)
C11A0.0270 (12)0.0320 (14)0.0250 (13)0.0062 (12)0.0001 (11)0.0063 (12)
Geometric parameters (Å, º) top
S1—C51.713 (3)C6—C6i1.525 (5)
S1—C21.722 (3)C8B—C12B1.341 (3)
C2—C31.401 (3)C8B—S9B1.562 (1)
C2—C8B1.447 (4)C12B—C11B1.69 (2)
C3—C41.391 (4)C12B—H12B0.9500
C3—H30.9500S9B—C10B1.503 (1)
C4—C51.361 (4)C10B—C11B1.338 (5)
C4—H40.9500C10B—H10B0.9500
C5—C61.500 (3)C11B—H11B0.9500
C6—O71.207 (3)C12A—H12A0.9500
C5—S1—C291.1 (1)C5—C6—C6i115.5 (2)
C3—C2—C8B128.2 (3)C12B—C8B—C2121.6 (10)
C3—C2—S1110.7 (2)C12B—C8B—S9B113.7 (1)
C8B—C2—S1121.1 (2)C2—C8B—S9B124.6 (6)
C4—C3—C2112.8 (3)C8B—C12B—C11B105.0 (12)
C4—C3—H3123.6C8B—C12B—H12B127.5
C2—C3—H3123.6C11B—C12B—H12B127.5
C5—C4—C3112.3 (2)C10B—S9B—C8B100.6 (8)
C5—C4—H4123.9C11B—C10B—S9B116.7 (5)
C3—C4—H4123.9C11B—C10B—H10B121.7
C4—C5—C6128.8 (2)S9B—C10B—H10B121.7
C4—C5—S1113.04 (19)C10B—C11B—C12B103.7 (3)
C6—C5—S1118.1 (2)C10B—C11B—H11B128.2
O7—C6—C5122.7 (2)C12B—C11B—H11B128.2
O7—C6—C6i121.5 (2)
C5—S1—C2—C31.6 (2)S1—C5—C6—C6i166.02 (13)
C5—S1—C2—C8B179.0 (2)C3—C2—C8B—C12B6.5 (13)
C8B—C2—C3—C4179.3 (3)S1—C2—C8B—C12B174.1 (12)
S1—C2—C3—C41.3 (3)C3—C2—C8B—S9B170.6 (6)
C2—C3—C4—C50.1 (4)S1—C2—C8B—S9B8.8 (6)
C3—C4—C5—C6177.5 (3)C2—C8B—C12B—C11B178.0 (5)
C3—C4—C5—S11.1 (3)S9B—C8B—C12B—C11B4.6 (17)
C2—S1—C5—C41.5 (2)C12B—C8B—S9B—C10B5.6 (13)
C2—S1—C5—C6177.2 (2)C2—C8B—S9B—C10B177.1 (4)
C4—C5—C6—O7174.0 (3)C8B—S9B—C10B—C11B4.5 (8)
S1—C5—C6—O77.5 (4)S9B—C10B—C11B—C12B2.0 (10)
C4—C5—C6—C6i12.5 (4)C8B—C12B—C11B—C10B1.7 (15)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O7i0.952.693.083 (3)105
Symmetry code: (i) x, y, z+1/2.
 

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