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The title compound, C12H12O2S2, is a chiral O,S-dialkyl dithio­carbonate. The O-ethyl substituent and the dithio­carbonate functionality form a plane, which is twisted by 60.7 (2)° from the S-(3-oxoindan-1-yl) group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023901/fl6178sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023901/fl6178Isup2.hkl
Contains datablock I

CCDC reference: 282350

Key indicators

  • Single-crystal X-ray study
  • T = 300 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.145
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.78 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON2002 (Spek, 1990, 2003) and ORTEP-3 for Windows (Farrugia, 1997, 2005); software used to prepare material for publication: SHELXL97.

O-Ethyl S-(3-oxoindan-1-yl) dithiocarbonate top
Crystal data top
C12H12O2S2F(000) = 528
Mr = 252.34Dx = 1.403 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.287 (6) ÅCell parameters from 703 reflections
b = 11.606 (6) Åθ = 2.9–19.1°
c = 9.864 (6) ŵ = 0.43 mm1
β = 112.39 (7)°T = 300 K
V = 1194.7 (11) Å3Prism, yellow
Z = 40.78 × 0.76 × 0.42 mm
Data collection top
Oxford Diffraction Xcalibur with Sapphire CCD detector
diffractometer
2426 independent reflections
Radiation source: fine-focus sealed tube1561 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
rotation method data acquisition using ω scansθmax = 26.4°, θmin = 4.1°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2002)
h = 914
Tmin = 0.718, Tmax = 0.881k = 1414
6892 measured reflectionsl = 1211
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)] = 0.047Hydrogen site location: difference Fourier map
wR(F2) = 0.145Only H-atom coordinates refined
S = 1.01 w = 1/[σ2(Fo2) + (0.0844P)2]
where P = (Fo2 + 2Fc2)/3
2426 reflections(Δ/σ)max = 0.010
182 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.29 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
C10.3052 (2)0.4960 (2)0.2047 (2)0.0589 (6)
C20.4466 (3)0.3585 (4)0.3647 (4)0.0836 (10)
H11A0.458 (3)0.309 (3)0.298 (4)0.100*
H11B0.510 (3)0.421 (3)0.397 (4)0.100*
C30.4493 (4)0.2894 (4)0.4885 (4)0.0923 (11)
H12A0.524 (3)0.259 (3)0.527 (4)0.111*
H12B0.429 (3)0.341 (3)0.561 (4)0.111*
H12C0.377 (4)0.238 (3)0.457 (4)0.111*
C40.0731 (2)0.5027 (2)0.2535 (3)0.0516 (6)
H10.004 (2)0.544 (2)0.220 (3)0.062*
C50.0457 (3)0.3743 (2)0.2375 (3)0.0566 (6)
H2A0.040 (2)0.359 (2)0.204 (3)0.068*
H2B0.081 (2)0.338 (2)0.174 (3)0.068*
C60.0989 (2)0.3255 (2)0.3895 (3)0.0547 (6)
C70.1479 (2)0.42054 (18)0.4922 (3)0.0490 (5)
C80.1366 (2)0.52186 (19)0.4157 (2)0.0475 (6)
C90.1816 (2)0.6229 (2)0.4911 (3)0.0649 (7)
H80.175 (3)0.691 (3)0.443 (3)0.078*
C100.2338 (3)0.6197 (3)0.6407 (3)0.0741 (8)
H70.267 (3)0.693 (3)0.691 (3)0.089*
C110.2436 (3)0.5187 (3)0.7161 (3)0.0739 (8)
H60.276 (3)0.519 (2)0.824 (3)0.089*
C120.2009 (3)0.4190 (3)0.6425 (3)0.0647 (7)
H50.206 (3)0.353 (2)0.691 (3)0.078*
O10.32358 (15)0.41718 (15)0.30607 (18)0.0619 (5)
O20.1003 (2)0.22494 (16)0.4202 (2)0.0847 (6)
S10.40507 (8)0.53620 (9)0.13130 (9)0.0953 (4)
S20.15805 (7)0.56180 (6)0.14667 (7)0.0664 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0612 (15)0.0752 (16)0.0373 (12)0.0107 (13)0.0154 (11)0.0027 (12)
C20.0693 (19)0.111 (3)0.072 (2)0.0316 (18)0.0295 (17)0.0057 (18)
C30.090 (2)0.107 (3)0.074 (2)0.043 (2)0.0237 (19)0.0164 (19)
C40.0467 (12)0.0535 (14)0.0528 (14)0.0067 (11)0.0169 (11)0.0069 (11)
C50.0560 (14)0.0588 (16)0.0536 (15)0.0063 (12)0.0193 (12)0.0062 (11)
C60.0593 (14)0.0535 (15)0.0556 (14)0.0068 (11)0.0269 (12)0.0001 (11)
C70.0470 (12)0.0536 (14)0.0499 (13)0.0015 (10)0.0224 (11)0.0021 (10)
C80.0439 (12)0.0488 (13)0.0486 (13)0.0068 (10)0.0164 (10)0.0028 (10)
C90.0657 (16)0.0483 (15)0.0764 (19)0.0068 (12)0.0222 (15)0.0092 (13)
C100.0663 (17)0.078 (2)0.072 (2)0.0036 (15)0.0195 (15)0.0289 (16)
C110.0623 (17)0.105 (2)0.0512 (16)0.0027 (16)0.0177 (14)0.0187 (17)
C120.0664 (16)0.080 (2)0.0490 (15)0.0013 (14)0.0236 (13)0.0035 (13)
O10.0549 (10)0.0800 (12)0.0545 (10)0.0144 (8)0.0251 (8)0.0143 (9)
O20.1195 (17)0.0517 (11)0.0822 (14)0.0181 (10)0.0373 (12)0.0041 (9)
S10.0829 (6)0.1464 (9)0.0669 (5)0.0268 (5)0.0400 (5)0.0037 (5)
S20.0695 (5)0.0711 (5)0.0534 (4)0.0009 (3)0.0174 (3)0.0206 (3)
Geometric parameters (Å, º) top
C1—O11.312 (3)C5—H2A0.92 (2)
C1—S11.624 (3)C5—H2B0.96 (2)
C1—S21.716 (3)C6—O21.204 (3)
C2—C31.451 (5)C6—C71.457 (3)
C2—O11.455 (3)C7—C121.371 (4)
C2—H11A0.92 (3)C7—C81.376 (3)
C2—H11B0.99 (3)C8—C91.378 (3)
C3—H12A0.85 (3)C9—C101.365 (4)
C3—H12B1.03 (4)C9—H80.91 (3)
C3—H12C0.96 (3)C10—C111.370 (5)
C4—C81.500 (3)C10—H70.99 (3)
C4—C51.518 (4)C11—C121.353 (4)
C4—S21.808 (3)C11—H60.98 (3)
C4—H10.94 (2)C12—H50.89 (3)
C5—C61.498 (4)
O1—C1—S1127.2 (2)C4—C5—H2B112.0 (15)
O1—C1—S2114.66 (18)H2A—C5—H2B109 (2)
S1—C1—S2118.13 (16)O2—C6—C7126.4 (2)
C3—C2—O1107.7 (3)O2—C6—C5125.4 (2)
C3—C2—H11A107 (2)C7—C6—C5108.1 (2)
O1—C2—H11A112 (2)C12—C7—C8121.0 (2)
C3—C2—H11B111 (2)C12—C7—C6129.5 (2)
O1—C2—H11B104.6 (19)C8—C7—C6109.5 (2)
H11A—C2—H11B114 (3)C7—C8—C9119.6 (2)
C2—C3—H12A107 (2)C7—C8—C4111.4 (2)
C2—C3—H12B109.1 (18)C9—C8—C4129.0 (2)
H12A—C3—H12B112 (3)C10—C9—C8118.6 (3)
C2—C3—H12C109 (2)C10—C9—H8120.1 (18)
H12A—C3—H12C118 (3)C8—C9—H8121.3 (18)
H12B—C3—H12C101 (3)C9—C10—C11121.5 (3)
C8—C4—C5104.63 (19)C9—C10—H7116.5 (17)
C8—C4—S2114.94 (17)C11—C10—H7121.9 (17)
C5—C4—S2116.39 (17)C12—C11—C10120.1 (3)
C8—C4—H1107.8 (16)C12—C11—H6119.4 (18)
C5—C4—H1109.9 (14)C10—C11—H6120.4 (18)
S2—C4—H1102.9 (15)C11—C12—C7119.2 (3)
C6—C5—C4106.2 (2)C11—C12—H5120.8 (19)
C6—C5—H2A104.7 (17)C7—C12—H5120.0 (19)
C4—C5—H2A112.1 (16)C1—O1—C2118.7 (2)
C6—C5—H2B112.4 (15)C1—S2—C4107.27 (12)
C8—C4—C5—C62.2 (2)S2—C4—C8—C951.1 (3)
S2—C4—C5—C6125.82 (19)C7—C8—C9—C101.5 (4)
C4—C5—C6—O2176.4 (2)C4—C8—C9—C10178.5 (2)
C4—C5—C6—C73.6 (3)C8—C9—C10—C110.9 (4)
O2—C6—C7—C122.6 (4)C9—C10—C11—C120.1 (5)
C5—C6—C7—C12177.3 (3)C10—C11—C12—C70.0 (4)
O2—C6—C7—C8176.3 (2)C8—C7—C12—C110.6 (4)
C5—C6—C7—C83.8 (3)C6—C7—C12—C11178.2 (2)
C12—C7—C8—C91.4 (4)S1—C1—O1—C21.4 (4)
C6—C7—C8—C9177.6 (2)S2—C1—O1—C2178.6 (2)
C12—C7—C8—C4178.6 (2)C3—C2—O1—C1171.6 (3)
C6—C7—C8—C42.4 (3)O1—C1—S2—C42.2 (2)
C5—C4—C8—C70.0 (3)S1—C1—S2—C4177.74 (14)
S2—C4—C8—C7128.94 (19)C8—C4—S2—C160.7 (2)
C5—C4—C8—C9180.0 (2)C5—C4—S2—C162.1 (2)
 

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