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In the crystal structure of the title compound, C
3H
3NO
2S
2, the four-membered C
2S
2 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
CCDC reference: 150839
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
C3H3NO2S2 | F(000) = 304 |
Mr = 149.18 | Dx = 1.786 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 3.9198 (1) Å | Cell parameters from 2751 reflections |
b = 18.3222 (5) Å | θ = 2.2–28.3° |
c = 7.9352 (2) Å | µ = 0.85 mm−1 |
β = 103.221 (2)° | T = 293 K |
V = 554.80 (3) Å3 | Slab, light green |
Z = 4 | 0.32 × 0.20 × 0.12 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 1359 independent reflections |
Radiation source: fine-focus sealed tube | 1108 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.2° |
ω scans | h = −5→3 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −23→24 |
Tmin = 0.772, Tmax = 0.904 | l = −10→10 |
3834 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-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 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
S1 | 0.20001 (15) | 0.08072 (3) | 0.44923 (6) | 0.03222 (18) | |
S2 | −0.03068 (15) | 0.19503 (3) | 0.59751 (7) | 0.03488 (19) | |
O1 | 0.0405 (5) | 0.17114 (10) | 0.9379 (2) | 0.0523 (5) | |
O2 | 0.2745 (7) | 0.07835 (11) | 1.0940 (2) | 0.0703 (7) | |
N1 | 0.1821 (5) | 0.11000 (12) | 0.9522 (2) | 0.0406 (5) | |
C1 | 0.0150 (7) | 0.16982 (12) | 0.3818 (3) | 0.0368 (5) | |
H1A | −0.2078 | 0.1670 | 0.2982 | 0.044* | |
H1B | 0.1756 | 0.2013 | 0.3391 | 0.044* | |
C2 | 0.1546 (5) | 0.11014 (11) | 0.6508 (2) | 0.0272 (4) | |
C3 | 0.2415 (6) | 0.07519 (12) | 0.8036 (3) | 0.0350 (5) | |
H3A | 0.3394 | 0.0287 | 0.8108 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0452 (4) | 0.0289 (3) | 0.0240 (3) | 0.0027 (2) | 0.0109 (2) | −0.00018 (19) |
S2 | 0.0434 (3) | 0.0240 (3) | 0.0371 (3) | 0.0027 (2) | 0.0089 (2) | −0.0015 (2) |
O1 | 0.0739 (13) | 0.0422 (10) | 0.0409 (9) | 0.0132 (9) | 0.0131 (9) | −0.0118 (8) |
O2 | 0.1147 (18) | 0.0728 (14) | 0.0242 (8) | 0.0303 (13) | 0.0172 (10) | 0.0074 (8) |
N1 | 0.0536 (12) | 0.0423 (11) | 0.0253 (9) | 0.0038 (9) | 0.0077 (8) | −0.0044 (8) |
C1 | 0.0453 (13) | 0.0320 (11) | 0.0330 (11) | 0.0006 (9) | 0.0087 (10) | 0.0071 (9) |
C2 | 0.0317 (11) | 0.0229 (9) | 0.0270 (9) | −0.0031 (8) | 0.0066 (8) | −0.0041 (7) |
C3 | 0.0504 (13) | 0.0307 (11) | 0.0243 (9) | 0.0044 (9) | 0.0095 (9) | −0.0041 (8) |
Geometric parameters (Å, º) top
S1—C2 | 1.735 (2) | N1—C3 | 1.406 (3) |
S1—C1 | 1.817 (2) | C1—H1A | 0.9700 |
S2—C2 | 1.728 (2) | C1—H1B | 0.9700 |
S2—C1 | 1.821 (2) | C2—C3 | 1.344 (3) |
O1—N1 | 1.244 (3) | C3—H3A | 0.9300 |
O2—N1 | 1.244 (2) | | |
| | | |
C2—S1—C1 | 82.8 (1) | S2—C1—H1B | 112.9 |
C2—S2—C1 | 82.9 (1) | H1A—C1—H1B | 110.3 |
O2—N1—O1 | 122.3 (2) | C3—C2—S2 | 131.0 (2) |
O2—N1—C3 | 118.5 (2) | C3—C2—S1 | 128.7 (2) |
O1—N1—C3 | 119.2 (2) | S2—C2—S1 | 100.4 (1) |
S1—C1—S2 | 94.00 (1) | C2—C3—N1 | 118.9 (2) |
S1—C1—H1A | 112.9 | C2—C3—H3A | 120.5 |
S2—C1—H1A | 112.9 | N1—C3—H3A | 120.5 |
S1—C1—H1B | 112.9 | | |
| | | |
C2—S1—C1—S2 | −1.10 (10) | C1—S1—C2—S2 | 1.17 (10) |
C2—S2—C1—S1 | 1.10 (10) | S2—C2—C3—N1 | −0.4 (4) |
C1—S2—C2—C3 | 178.9 (2) | S1—C2—C3—N1 | 179.70 (17) |
C1—S2—C2—S1 | −1.17 (10) | O2—N1—C3—C2 | −177.5 (2) |
C1—S1—C2—C3 | −178.9 (2) | O1—N1—C3—C2 | 2.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O2i | 0.93 | 2.49 | 3.387 (3) | 163 |
Symmetry code: (i) −x+1, −y, −z+2. |
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