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In the crystal structure of the title compound, C3H3NO2S2, the four-membered C2S2 ring is planar, as is the whole mol­ecule. The short intramolecular S...O distance of 2.687 (2) Å shows the five-atom system to be conjugated. The mol­ecules pack as a two-dimensional network in the (010) plane through short intermolecular S...O [2.900 (2) and 3.077 (2) Å] interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100009100/sk1398sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100009100/sk1398Isup2.hkl
Contains datablock I

CCDC reference: 150839

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

2-(Nitromethylene)-1,3-dithietane top
Crystal data top
C3H3NO2S2F(000) = 304
Mr = 149.18Dx = 1.786 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 3.9198 (1) ÅCell parameters from 2751 reflections
b = 18.3222 (5) Åθ = 2.2–28.3°
c = 7.9352 (2) ŵ = 0.85 mm1
β = 103.221 (2)°T = 293 K
V = 554.80 (3) Å3Slab, light green
Z = 40.32 × 0.20 × 0.12 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
1359 independent reflections
Radiation source: fine-focus sealed tube1108 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.2°
ω scansh = 53
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 2324
Tmin = 0.772, Tmax = 0.904l = 1010
3834 measured reflections
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0538P)2]
where P = (Fo2 + 2Fc2)/3
1359 reflections(Δ/σ)max < 0.001
73 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.55 e Å3
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible.

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
S10.20001 (15)0.08072 (3)0.44923 (6)0.03222 (18)
S20.03068 (15)0.19503 (3)0.59751 (7)0.03488 (19)
O10.0405 (5)0.17114 (10)0.9379 (2)0.0523 (5)
O20.2745 (7)0.07835 (11)1.0940 (2)0.0703 (7)
N10.1821 (5)0.11000 (12)0.9522 (2)0.0406 (5)
C10.0150 (7)0.16982 (12)0.3818 (3)0.0368 (5)
H1A0.20780.16700.29820.044*
H1B0.17560.20130.33910.044*
C20.1546 (5)0.11014 (11)0.6508 (2)0.0272 (4)
C30.2415 (6)0.07519 (12)0.8036 (3)0.0350 (5)
H3A0.33940.02870.81080.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0452 (4)0.0289 (3)0.0240 (3)0.0027 (2)0.0109 (2)0.00018 (19)
S20.0434 (3)0.0240 (3)0.0371 (3)0.0027 (2)0.0089 (2)0.0015 (2)
O10.0739 (13)0.0422 (10)0.0409 (9)0.0132 (9)0.0131 (9)0.0118 (8)
O20.1147 (18)0.0728 (14)0.0242 (8)0.0303 (13)0.0172 (10)0.0074 (8)
N10.0536 (12)0.0423 (11)0.0253 (9)0.0038 (9)0.0077 (8)0.0044 (8)
C10.0453 (13)0.0320 (11)0.0330 (11)0.0006 (9)0.0087 (10)0.0071 (9)
C20.0317 (11)0.0229 (9)0.0270 (9)0.0031 (8)0.0066 (8)0.0041 (7)
C30.0504 (13)0.0307 (11)0.0243 (9)0.0044 (9)0.0095 (9)0.0041 (8)
Geometric parameters (Å, º) top
S1—C21.735 (2)N1—C31.406 (3)
S1—C11.817 (2)C1—H1A0.9700
S2—C21.728 (2)C1—H1B0.9700
S2—C11.821 (2)C2—C31.344 (3)
O1—N11.244 (3)C3—H3A0.9300
O2—N11.244 (2)
C2—S1—C182.8 (1)S2—C1—H1B112.9
C2—S2—C182.9 (1)H1A—C1—H1B110.3
O2—N1—O1122.3 (2)C3—C2—S2131.0 (2)
O2—N1—C3118.5 (2)C3—C2—S1128.7 (2)
O1—N1—C3119.2 (2)S2—C2—S1100.4 (1)
S1—C1—S294.00 (1)C2—C3—N1118.9 (2)
S1—C1—H1A112.9C2—C3—H3A120.5
S2—C1—H1A112.9N1—C3—H3A120.5
S1—C1—H1B112.9
C2—S1—C1—S21.10 (10)C1—S1—C2—S21.17 (10)
C2—S2—C1—S11.10 (10)S2—C2—C3—N10.4 (4)
C1—S2—C2—C3178.9 (2)S1—C2—C3—N1179.70 (17)
C1—S2—C2—S11.17 (10)O2—N1—C3—C2177.5 (2)
C1—S1—C2—C3178.9 (2)O1—N1—C3—C22.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···O2i0.932.493.387 (3)163
Symmetry code: (i) x+1, y, z+2.
 

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