Buy article online - an online subscription or single-article purchase is required to access this article.
The molecule of the title compound, C12H10O2S2, is disposed about a centre of inversion and is essentially planar.
Supporting information
CCDC reference: 285521
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.047
- wR factor = 0.052
- Data-to-parameter ratio = 10.2
checkCIF/PLATON results
No syntax errors found
Alert level A
DIFF020_ALERT_1_A _diffrn_standards_interval_count and
_diffrn_standards_interval_time are missing. Number of measurements
between standards or time (min) between standards.
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 22.30 Deg.
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C1_a ... 1.54 Ang.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C6
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CRYSTALS.
1,2-Bis(3-methyl-2-thienyl)ethane-1,2-dione
top
Crystal data top
C12H10O2S2 | F(000) = 260 |
Mr = 250.34 | Dx = 1.423 Mg m−3 |
Monoclinic, P21/n | Melting point: 343 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 9.605 (3) Å | Cell parameters from 3871 reflections |
b = 5.0901 (16) Å | θ = 3.7–29.6° |
c = 12.193 (4) Å | µ = 0.44 mm−1 |
β = 101.37 (2)° | T = 293 K |
V = 584.4 (3) Å3 | Plate, yellow |
Z = 2 | 0.26 × 0.15 × 0.01 mm |
Data collection top
Oxford Diffraction Sapphire3 diffractometer | 743 reflections with I > 3u(I) |
Graphite monochromator | Rint = 0.051 |
ω scans | θmax = 29.7°, θmin = 4.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −13→13 |
Tmin = 0.865, Tmax = 1 | k = −6→6 |
3871 measured reflections | l = −15→14 |
1452 independent reflections | |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.052 | H-atom parameters constrained |
S = 1.13 | Method, part 1, Chebychev polynomial, (Watkin, 1994; Prince, 1982)
w = 1/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)] where Ai are the
Chebychev coefficients listed below and x = F /Fmax Method = Robust
Weighting (Prince, 1982) W = w[1-(δF/6σF)2]2; Ai are: 0.352,
0.362, 0.186 and 0.0821 |
743 reflections | (Δ/σ)max < 0.001 |
73 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 1.09519 (9) | 0.1944 (2) | 0.70322 (8) | 0.0574 | |
C2 | 0.9456 (3) | 0.2265 (7) | 0.5971 (3) | 0.0440 | |
O1 | 0.8237 (2) | 0.4454 (6) | 0.4367 (2) | 0.0713 | |
C1 | 0.9344 (3) | 0.4180 (7) | 0.5058 (3) | 0.0477 | |
C3 | 0.8393 (3) | 0.0519 (7) | 0.6123 (3) | 0.0478 | |
C6 | 0.6942 (4) | 0.0273 (9) | 0.5380 (3) | 0.0639 | |
H7 | 0.6451 | 0.1922 | 0.5355 | 0.0500* | |
H8 | 0.6408 | −0.1066 | 0.5657 | 0.0500* | |
H6 | 0.7045 | −0.0182 | 0.4628 | 0.0500* | |
C4 | 0.8824 (4) | −0.1061 (8) | 0.7075 (3) | 0.0598 | |
H4 | 0.8255 | −0.2355 | 0.7309 | 0.0500* | |
C5 | 1.0166 (4) | −0.0492 (9) | 0.7647 (3) | 0.0644 | |
H5 | 1.0614 | −0.1330 | 0.8295 | 0.0500* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0440 (5) | 0.0636 (6) | 0.0555 (5) | −0.0021 (5) | −0.0123 (3) | 0.0092 (5) |
C2 | 0.0380 (16) | 0.051 (2) | 0.0393 (16) | 0.0008 (15) | −0.0016 (12) | −0.0051 (15) |
O1 | 0.0466 (14) | 0.087 (2) | 0.0671 (16) | −0.0163 (14) | −0.0225 (12) | 0.0252 (15) |
C1 | 0.0422 (17) | 0.053 (2) | 0.0421 (17) | −0.0064 (16) | −0.0048 (14) | −0.0024 (17) |
C3 | 0.0425 (17) | 0.054 (2) | 0.0448 (17) | −0.0004 (16) | 0.0024 (13) | −0.0062 (17) |
C6 | 0.047 (2) | 0.080 (3) | 0.060 (2) | −0.017 (2) | −0.0013 (17) | −0.001 (2) |
C4 | 0.052 (2) | 0.061 (3) | 0.066 (2) | −0.0042 (18) | 0.0102 (17) | 0.011 (2) |
C5 | 0.057 (2) | 0.070 (3) | 0.060 (2) | 0.001 (2) | −0.0043 (18) | 0.023 (2) |
Geometric parameters (Å, º) top
S1—C2 | 1.741 (3) | C3—C6 | 1.511 (5) |
S1—C5 | 1.701 (4) | C6—H7 | 0.961 |
C2—C1 | 1.468 (5) | C6—H8 | 0.955 |
C2—C3 | 1.394 (5) | C6—H6 | 0.969 |
O1—C1 | 1.227 (4) | C4—H4 | 0.935 |
C1—C1i | 1.542 (6) | C4—C5 | 1.370 (5) |
C3—C4 | 1.405 (5) | C5—H5 | 0.927 |
| | | |
C2—S1—C5 | 91.31 (17) | C3—C6—H8 | 110.085 |
S1—C2—C1 | 123.6 (2) | H7—C6—H8 | 109.874 |
S1—C2—C3 | 111.1 (3) | C3—C6—H6 | 109.473 |
C1—C2—C3 | 125.3 (3) | H7—C6—H6 | 108.633 |
C1i—C1—O1 | 119.3 (4) | H8—C6—H6 | 109.121 |
C1i—C1—C2 | 119.3 (3) | C3—C4—H4 | 124.075 |
C2—C1—O1 | 121.4 (3) | C3—C4—C5 | 113.2 (3) |
C2—C3—C4 | 111.8 (3) | H4—C4—C5 | 122.756 |
C2—C3—C6 | 125.9 (3) | S1—C5—C4 | 112.6 (3) |
C6—C3—C4 | 122.3 (3) | C4—C5—H5 | 124.675 |
C3—C6—H7 | 109.630 | S1—C5—H5 | 122.682 |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.