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The title compound, C10H8O2S2, is the 2-thienyl symmetric analog of benzoin. 2,2'-Thenoin can be synthesized in good yield utilizing the benzoin condensation reaction (starting with 2-thio­phene­carbox­aldehyde). The crystal structure of 2,2'-thenoin has been determined at room temperature.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008516/cm6004sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008516/cm6004Isup2.hkl
Contains datablock I

CCDC reference: 189400

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.048
  • wR factor = 0.172
  • Data-to-parameter ratio = 9.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
THETM_01 Alert A The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.5207
Author response: Data was collected on several samples and this was the best data set obtained for these small platelike crystals.

Yellow Alert Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 10 for a centrosymmetric structure sine(theta)/lambda 0.5207 Proportion of unique data used 1.0000 Ratio reflections to parameters 9.3150
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SHELXTL-Plus (Sheldrick, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

1,2-di-2-thienyl-2-hydroxyethanone top
Crystal data top
C10H8O2S2Dx = 1.483 Mg m3
Mr = 224.28Melting point: 117-118° K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.8436 (11) ÅCell parameters from 3834 reflections
b = 6.0348 (6) Åθ = 2.0–23.3°
c = 16.336 (2) ŵ = 0.50 mm1
β = 110.001 (2)°T = 294 K
V = 1004.55 (19) Å3Plate, colorless
Z = 40.2 × 0.1 × 0.1 mm
F(000) = 464
Data collection top
Siemens SMART P3/512CCD
diffractometer
1010 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 21.7°, θmin = 2.0°
ω scansh = 115
3645 measured reflectionsk = 66
1183 independent reflectionsl = 1417
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173H-atom parameters constrained
S = 1.37 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
1183 reflections(Δ/σ)max = 0.003
127 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.35 e Å3
Special details top

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*/Ueq
S10.15529 (13)0.2560 (2)0.00550 (8)0.0554 (6)
O10.1107 (3)0.1771 (5)0.1613 (2)0.0507 (9)
C10.1333 (4)0.3704 (8)0.1516 (2)0.0359 (11)
S20.37359 (14)0.4110 (2)0.34324 (9)0.0657 (6)
O20.0627 (3)0.4570 (5)0.27023 (19)0.0506 (10)
H2A0.01930.55580.28170.076*
C20.1625 (4)0.4455 (7)0.0747 (3)0.0383 (11)
C30.1947 (5)0.6554 (7)0.0532 (3)0.0447 (12)
H3A0.20510.77980.08850.054*
C40.2095 (5)0.6546 (9)0.0292 (3)0.0607 (15)
H4A0.23000.77990.05510.073*
C50.1907 (5)0.4507 (9)0.0665 (3)0.0562 (14)
H5A0.19690.42220.12090.067*
C60.1352 (4)0.5454 (7)0.2201 (3)0.0365 (11)
H6A0.09140.67980.19040.044*
C70.2735 (4)0.6009 (7)0.2743 (3)0.0376 (11)
C80.3400 (4)0.8026 (7)0.2791 (3)0.0438 (12)
H8A0.30360.92890.24750.053*
C90.4696 (6)0.7881 (10)0.3385 (4)0.0699 (16)
H9A0.52870.90540.34940.084*
C100.4995 (5)0.5929 (10)0.3771 (4)0.0702 (16)
H10A0.58080.55940.41830.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0633 (10)0.0502 (9)0.0530 (9)0.0110 (6)0.0201 (7)0.0079 (6)
O10.062 (2)0.037 (2)0.059 (2)0.0017 (17)0.0270 (17)0.0004 (15)
C10.029 (2)0.040 (3)0.037 (2)0.003 (2)0.0094 (19)0.002 (2)
S20.0555 (10)0.0587 (10)0.0713 (10)0.0004 (7)0.0066 (7)0.0114 (7)
O20.050 (2)0.058 (2)0.0559 (19)0.0028 (17)0.0327 (17)0.0028 (16)
C20.033 (3)0.046 (3)0.035 (2)0.003 (2)0.0101 (19)0.003 (2)
C30.067 (3)0.034 (3)0.039 (3)0.003 (2)0.025 (2)0.002 (2)
C40.080 (4)0.060 (3)0.052 (3)0.005 (3)0.035 (3)0.010 (3)
C50.063 (3)0.070 (4)0.042 (3)0.018 (3)0.027 (3)0.006 (3)
C60.035 (3)0.038 (3)0.040 (2)0.003 (2)0.018 (2)0.006 (2)
C70.045 (3)0.040 (3)0.031 (2)0.001 (2)0.018 (2)0.0043 (19)
C80.040 (3)0.038 (3)0.048 (3)0.005 (2)0.010 (2)0.002 (2)
C90.062 (4)0.060 (4)0.087 (4)0.022 (3)0.024 (3)0.014 (3)
C100.042 (3)0.083 (4)0.071 (4)0.002 (3)0.000 (3)0.003 (3)
Geometric parameters (Å, º) top
S1—C51.668 (5)C4—C51.357 (7)
S1—C21.721 (4)C4—H4A0.9300
O1—C11.214 (5)C5—H5A0.9300
C1—C21.468 (6)C6—C71.495 (6)
C1—C61.533 (6)C6—H6A0.9800
S2—C101.691 (6)C7—C81.403 (6)
S2—C71.710 (4)C8—C91.410 (7)
O2—C61.419 (5)C8—H8A0.9300
O2—H2A0.8200C9—C101.324 (7)
C2—C31.390 (6)C9—H9A0.9300
C3—C41.409 (6)C10—H10A0.9300
C3—H3A0.9300
C5—S1—C291.6 (2)O2—C6—C7112.6 (3)
O1—C1—C2121.4 (4)O2—C6—C1106.9 (3)
O1—C1—C6121.3 (4)C7—C6—C1110.3 (3)
C2—C1—C6117.3 (4)O2—C6—H6A109.0
C10—S2—C792.3 (3)C7—C6—H6A109.0
C6—O2—H2A109.5C1—C6—H6A109.0
C3—C2—C1130.1 (4)C8—C7—C6128.3 (4)
C3—C2—S1111.3 (3)C8—C7—S2110.2 (3)
C1—C2—S1118.7 (3)C6—C7—S2121.5 (3)
C2—C3—C4111.0 (4)C7—C8—C9110.9 (4)
C2—C3—H3A124.5C7—C8—H8A124.5
C4—C3—H3A124.5C9—C8—H8A124.5
C5—C4—C3112.6 (4)C10—C9—C8114.0 (5)
C5—C4—H4A123.7C10—C9—H9A123.0
C3—C4—H4A123.7C8—C9—H9A123.0
C4—C5—S1113.6 (3)C9—C10—S2112.5 (4)
C4—C5—H5A123.2C9—C10—H10A123.8
S1—C5—H5A123.2S2—C10—H10A123.8
 

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