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The title compound, C12H18O4S2, exhibits fungicidal activity. A short S...S intermolecular contact [3.576 (3)Å] is observed in the crystal structure, which is further stabilized by C—H...O intermolecular interactions, forming molecular chains along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030934/sj6026sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030934/sj6026Isup2.hkl
Contains datablock I

CCDC reference: 262421

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.090
  • wR factor = 0.205
  • Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.54 Ratio
Author Response: The carbon atoms C7 and C8 of the isopropyl group have large thermal parameters compared to the riding hydrogen and hence the ratio Ueq(max)/Ueq(min) has a large value.
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       6.68 Ratio
Author Response: The carbon atoms C7 and C8 of the isopropyl group have large thermal parameters compared to the riding hydrogen and hence the ratio Ueq(max)/Ueq(min) has a large value.
PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for         C9
Author Response: In the isopropyl group, the thermal parameters of carbon atoms C7 and C8 is greater than that of C9 to which these are connected. This is due to greater vibrational freedom of the carbon atoms C7 and C8 compared to C9.

Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5
Author Response: In the isopropyl group, the thermal parameters of carbon atoms C7 and C8 is greater than that of C9 to which these are connected. This is due to greater vibrational freedom of the carbon atoms C7 and C8 compared to C9.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
Author Response: In the isopropyl group, the thermal parameters of carbon atoms C7 and C8 is greater than that of C9 to which these are connected. This is due to greater vibrational freedom of the carbon atoms C7 and C8 compared to C9.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C7     -   C9     ...       1.40 Ang.

3 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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 1990).

diisopropyl (1,3-dithiolan-2-ylidene)malonate top
Crystal data top
C12H18O4S2F(000) = 1232
Mr = 290.40Dx = 1.268 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 675 reflections
a = 10.400 (7) Åθ = 1.9–24.4°
b = 9.117 (6) ŵ = 0.35 mm1
c = 32.09 (2) ÅT = 293 K
V = 3043 (3) Å3Block, colorless
Z = 80.23 × 0.11 × 0.02 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2681 independent reflections
Radiation source: fine-focus sealed tube1925 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
φ and ω scansθmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1211
Tmin = 0.943, Tmax = 0.993k = 1010
20345 measured reflectionsl = 3834
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)] = 0.090Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.205H atoms treated by a mixture of independent and constrained refinement
S = 1.22 w = 1/[σ2(Fo2) + (0.0874P)2 + 1.215P]
where P = (Fo2 + 2Fc2)/3
2681 reflections(Δ/σ)max = 0.001
191 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.22 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
S10.74652 (12)0.09080 (16)0.59790 (4)0.0777 (5)
S20.92128 (11)0.14398 (13)0.52795 (4)0.0653 (4)
O10.8733 (5)0.1781 (6)0.67037 (13)0.1322 (19)
O21.1185 (3)0.3271 (4)0.55557 (11)0.0825 (11)
O31.1891 (3)0.2926 (4)0.62048 (10)0.0712 (9)
O40.9837 (4)0.3851 (4)0.66638 (11)0.0886 (11)
C10.7926 (5)0.0139 (6)0.5189 (2)0.0733 (14)
C20.6832 (5)0.0569 (6)0.54649 (19)0.0737 (15)
C30.8923 (4)0.1680 (4)0.58113 (15)0.0572 (12)
C40.9743 (4)0.2402 (5)0.60720 (14)0.0563 (11)
C50.9391 (5)0.2614 (6)0.65102 (16)0.0734 (14)
C61.0992 (4)0.2917 (5)0.59100 (16)0.0580 (11)
C70.8881 (12)0.5431 (16)0.7129 (3)0.254 (8)
C81.0887 (11)0.4374 (17)0.7311 (3)0.225 (6)
C90.9611 (8)0.4148 (10)0.7112 (2)0.111 (2)
C101.3179 (5)0.3493 (7)0.61023 (19)0.0764 (15)
C111.3952 (6)0.2307 (9)0.5908 (2)0.121 (2)
C121.3727 (6)0.4053 (8)0.6509 (2)0.115 (2)
H1A0.773 (5)0.014 (6)0.4896 (19)0.096 (19)*
H1B0.830 (5)0.084 (6)0.5265 (15)0.086 (15)*
H2A0.621 (5)0.014 (5)0.5489 (13)0.067 (13)*
H2B0.641 (5)0.147 (5)0.5367 (14)0.075 (14)*
H7A0.93300.62070.69890.381*
H7B0.87430.57000.74150.381*
H7C0.80670.52700.69960.381*
H8A1.12800.52430.72000.337*
H8B1.14280.35430.72560.337*
H8C1.07770.44830.76070.337*
H90.941 (5)0.326 (6)0.7277 (17)0.089 (18)*
H101.316 (4)0.434 (5)0.5952 (13)0.057 (13)*
H11A1.39830.14790.60930.182*
H11B1.48080.26550.58570.182*
H11C1.35630.20210.56490.182*
H12A1.32170.48610.66070.173*
H12B1.45960.43750.64660.173*
H12C1.37150.32810.67120.173*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0608 (8)0.0879 (10)0.0843 (10)0.0183 (7)0.0118 (7)0.0085 (7)
S20.0597 (7)0.0664 (8)0.0697 (8)0.0022 (6)0.0093 (6)0.0093 (6)
O10.167 (4)0.150 (4)0.079 (3)0.082 (4)0.039 (3)0.002 (3)
O20.066 (2)0.120 (3)0.062 (2)0.025 (2)0.0046 (17)0.014 (2)
O30.0538 (18)0.087 (2)0.073 (2)0.0062 (16)0.0018 (16)0.0172 (18)
O40.109 (3)0.092 (3)0.064 (2)0.021 (2)0.024 (2)0.0106 (19)
C10.067 (3)0.061 (3)0.093 (4)0.001 (3)0.003 (3)0.010 (3)
C20.054 (3)0.057 (3)0.110 (4)0.009 (3)0.004 (3)0.003 (3)
C30.051 (2)0.049 (3)0.071 (3)0.008 (2)0.009 (2)0.013 (2)
C40.053 (3)0.057 (3)0.058 (3)0.001 (2)0.004 (2)0.005 (2)
C50.065 (3)0.085 (4)0.070 (3)0.015 (3)0.006 (3)0.007 (3)
C60.055 (3)0.058 (3)0.061 (3)0.003 (2)0.003 (2)0.004 (2)
C70.286 (14)0.375 (18)0.100 (6)0.226 (14)0.019 (8)0.047 (9)
C80.191 (11)0.380 (18)0.104 (7)0.054 (11)0.029 (7)0.059 (9)
C90.127 (6)0.129 (6)0.076 (5)0.017 (5)0.019 (4)0.017 (4)
C100.057 (3)0.081 (4)0.091 (4)0.012 (3)0.000 (3)0.016 (3)
C110.064 (4)0.134 (6)0.167 (7)0.007 (4)0.010 (4)0.018 (5)
C120.097 (5)0.129 (6)0.120 (6)0.031 (4)0.024 (4)0.002 (4)
Geometric parameters (Å, º) top
C1—C21.494 (8)C9—C71.396 (12)
C1—H1A0.96 (6)C9—C81.488 (12)
C1—H1B1.01 (5)C9—H90.99 (5)
S1—C21.803 (6)C8—H8A0.9600
S1—C31.756 (4)C8—H8B0.9600
S2—C11.811 (5)C8—H8C0.9600
S2—C31.747 (5)C10—C111.484 (8)
C3—C41.364 (6)C10—C121.512 (8)
C4—C51.466 (7)C10—H100.91 (4)
C6—C41.477 (6)C11—H11A0.9600
O2—C61.199 (5)C11—H11B0.9600
O3—C61.330 (5)C11—H11C0.9600
C5—O11.196 (6)C12—H12A0.9600
O4—C51.315 (6)C12—H12B0.9600
O3—C101.473 (6)C12—H12C0.9600
O4—C91.481 (7)C7—H7A0.9600
C2—H2A0.92 (5)C7—H7B0.9600
C2—H2B0.98 (5)C7—H7C0.9600
C3—S1—C296.0 (2)O4—C9—H9114 (3)
C3—S2—C196.4 (3)C8—C9—H994 (3)
C4—C3—S1123.0 (4)C9—C8—H8A109.5
C4—C3—S2123.5 (3)C9—C8—H8B109.5
C3—C4—C5119.7 (4)H8A—C8—H8B109.5
C3—C4—C6119.2 (4)C9—C8—H8C109.5
C5—C4—C6121.0 (4)H8A—C8—H8C109.5
C6—O3—C10118.8 (4)H8B—C8—H8C109.5
O2—C6—O3123.8 (4)O3—C10—C11109.3 (5)
O2—C6—C4124.5 (4)O3—C10—C12105.6 (5)
O3—C6—C4111.7 (4)C11—C10—C12113.8 (6)
C2—C1—S2107.2 (4)O3—C10—H10113 (3)
C2—C1—H1A115 (3)C11—C10—H10114 (3)
S2—C1—H1A108 (3)C12—C10—H10100 (3)
C2—C1—H1B113 (3)C10—C11—H11A109.5
S2—C1—H1B105 (3)C10—C11—H11B109.5
H1A—C1—H1B109 (4)H11A—C11—H11B109.5
S2—C3—S1113.5 (3)C10—C11—H11C109.5
C5—O4—C9117.7 (5)H11A—C11—H11C109.5
O1—C5—O4123.5 (5)H11B—C11—H11C109.5
O1—C5—C4123.8 (5)C10—C12—H12A109.5
O4—C5—C4112.6 (4)C10—C12—H12B109.5
C1—C2—S1108.0 (4)H12A—C12—H12B109.5
C1—C2—H2A114 (3)C10—C12—H12C109.5
S1—C2—H2A107 (3)H12A—C12—H12C109.5
C1—C2—H2B112 (3)H12B—C12—H12C109.5
S1—C2—H2B108 (3)C9—C7—H7A109.5
H2A—C2—H2B107 (4)C9—C7—H7B109.5
C7—C9—O4106.2 (7)H7A—C7—H7B109.5
C7—C9—C8110.6 (10)C9—C7—H7C109.5
O4—C9—C8107.6 (6)H7A—C7—H7C109.5
C7—C9—H9123 (3)H7B—C7—H7C109.5
C10—O3—C6—O24.3 (7)O3—C6—C4—C528.7 (6)
C10—O3—C6—C4176.5 (4)C9—O4—C5—O16.0 (9)
C3—S2—C1—C235.1 (5)C9—O4—C5—C4176.4 (5)
C1—S2—C3—C4169.4 (4)C3—C4—C5—O130.4 (8)
C1—S2—C3—S110.8 (3)C6—C4—C5—O1147.7 (6)
C2—S1—C3—C4168.1 (4)C3—C4—C5—O4147.1 (4)
C2—S1—C3—S211.6 (3)C6—C4—C5—O434.8 (6)
S2—C3—C4—C5177.0 (3)S2—C1—C2—S146.9 (5)
S1—C3—C4—C52.7 (6)C3—S1—C2—C135.9 (4)
S2—C3—C4—C64.9 (6)C5—O4—C9—C7119.0 (9)
S1—C3—C4—C6175.4 (3)C5—O4—C9—C8122.6 (9)
O2—C6—C4—C329.8 (7)C6—O3—C10—C1184.3 (6)
O3—C6—C4—C3149.4 (4)C6—O3—C10—C12152.9 (5)
O2—C6—C4—C5152.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7C···O1i0.962.513.281 (19)138 (1)
Symmetry code: (i) x+3/2, y+1/2, z.
 

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