Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033946/rz2153sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033946/rz2153Isup2.hkl |
CCDC reference: 657785
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C)= 0.002 Å
- R factor = 0.024
- wR factor = 0.065
- Data-to-parameter ratio = 12.4
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
A solution of methylsulfonyl chloride (1 mmol) dissolved in anhydrous CH2Cl2 (10 ml) was added dropwise over a period of 10 min to a solution of 2-nitro-N-methyl-benzenesulfonamide (1 mmol) and EtN(iPr)2 (3 mmol) in CH2Cl2 (10 ml) at 273 K. The mixture was stirred at room temperature for 4 h. The organic phase was washed twice with 2 N HCl and dried over anhydrous Na2SO4. The solvent was removed and the residue was purified by flash chromatography (1:1 cyclohexane/dichloromethane) to give the title compound as a white solid (147 mg, yield 64%). Single crystals suitable for X-ray measurements were obtained by slow evaporation of an ethanol/dichloromethane solution (1:1 v/v) at room temperature.
All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95–0.98 Å and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl groups.
Many compounds containing sulfonimide groups possess a broad spectrum of biological activities and can be widely used as herbicides (Kamoshita et al., 1987). Their use as catalysts is also reported (Zhang et al., 2007). Here, we report the synthesis and crystal structure of the title compound.
In the title compound (Fig. 1), all bond lengths and angles are normal (Allen et al., 1987) and in good agreement with those reported previously for similar molecules (Henschel et al., 1996). The molecular structure is stabilized by intramolecular C—H···O hydrogen bonds involving the oxygen atoms bound to atom S1 (Table 1). In the crystal structure (Fig. 2), molecules are linked into a three-dimensional network by weak intermolecular C—H···O hydrogen bonds and aromatic π-π stacking interactions (Cg···Cgi = 4.078 (2) Å; Cg is the centroid of the C1—C6 benzene ring; symmetry code: (i) x, 3/2 - y, -1/2 + z).
For literature on the biological activities of sulfonimide-containing compounds, see: Kamoshita et al. (1987). For the crystal structure of related compounds, see: Henschel et al. (1996).
For related literature, see: Allen et al. (1987); Zhang et al. (2007).
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C8H10N2O6S2 | F(000) = 608 |
Mr = 294.30 | Dx = 1.689 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2541 reflections |
a = 6.9540 (14) Å | θ = 6.2–55.0° |
b = 20.492 (4) Å | µ = 0.48 mm−1 |
c = 8.1272 (16) Å | T = 153 K |
β = 92.53 (3)° | Block, colourless |
V = 1157.0 (4) Å3 | 0.44 × 0.23 × 0.12 mm |
Z = 4 |
Rigaku R-AXIS RAPID IP area-detector diffractometer | 2040 independent reflections |
Radiation source: Rotating Anode | 1937 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω oscillation scans | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan (ABSCOR; Higashi 1995) | h = −8→7 |
Tmin = 0.818, Tmax = 0.945 | k = −24→24 |
9002 measured reflections | l = −9→9 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.065 | w = 1/[σ2(Fo2) + (0.0299P)2 + 0.8042P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.002 |
2040 reflections | Δρmax = 0.32 e Å−3 |
164 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0257 (16) |
C8H10N2O6S2 | V = 1157.0 (4) Å3 |
Mr = 294.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.9540 (14) Å | µ = 0.48 mm−1 |
b = 20.492 (4) Å | T = 153 K |
c = 8.1272 (16) Å | 0.44 × 0.23 × 0.12 mm |
β = 92.53 (3)° |
Rigaku R-AXIS RAPID IP area-detector diffractometer | 2040 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi 1995) | 1937 reflections with I > 2σ(I) |
Tmin = 0.818, Tmax = 0.945 | Rint = 0.018 |
9002 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | 0 restraints |
wR(F2) = 0.065 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.32 e Å−3 |
2040 reflections | Δρmin = −0.32 e Å−3 |
164 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.36867 (5) | 0.613945 (18) | 0.45674 (5) | 0.01797 (13) | |
S2 | 0.17510 (5) | 0.544118 (18) | 0.18890 (5) | 0.01806 (13) | |
O1 | 0.55828 (18) | 0.80933 (6) | 0.35423 (15) | 0.0297 (3) | |
O2 | 0.52506 (17) | 0.71668 (6) | 0.22789 (14) | 0.0270 (3) | |
O3 | 0.27241 (18) | 0.56917 (6) | 0.56005 (14) | 0.0278 (3) | |
O4 | 0.56186 (16) | 0.63251 (6) | 0.49936 (14) | 0.0256 (3) | |
O5 | 0.01285 (16) | 0.57654 (6) | 0.25138 (15) | 0.0256 (3) | |
O6 | 0.19992 (17) | 0.54204 (6) | 0.01525 (14) | 0.0255 (3) | |
N1 | 0.37021 (18) | 0.58253 (6) | 0.26787 (16) | 0.0185 (3) | |
N2 | 0.47199 (19) | 0.75836 (7) | 0.32402 (16) | 0.0196 (3) | |
C1 | 0.0432 (2) | 0.68091 (9) | 0.51230 (19) | 0.0229 (4) | |
H1A | −0.0040 | 0.6393 | 0.5429 | 0.027* | |
C2 | −0.0693 (2) | 0.73588 (9) | 0.5334 (2) | 0.0275 (4) | |
H2A | −0.1934 | 0.7318 | 0.5766 | 0.033* | |
C3 | −0.0008 (3) | 0.79664 (9) | 0.4915 (2) | 0.0279 (4) | |
H3B | −0.0772 | 0.8343 | 0.5079 | 0.033* | |
C4 | 0.1787 (2) | 0.80291 (8) | 0.4258 (2) | 0.0240 (4) | |
H4B | 0.2259 | 0.8447 | 0.3971 | 0.029* | |
C5 | 0.2881 (2) | 0.74774 (8) | 0.40254 (18) | 0.0176 (3) | |
C6 | 0.2241 (2) | 0.68580 (8) | 0.44701 (18) | 0.0172 (3) | |
C8 | 0.5563 (2) | 0.57088 (9) | 0.1902 (2) | 0.0275 (4) | |
H8A | 0.6578 | 0.5961 | 0.2483 | 0.041* | |
H8B | 0.5458 | 0.5845 | 0.0745 | 0.041* | |
H8C | 0.5880 | 0.5243 | 0.1963 | 0.041* | |
C9 | 0.1866 (3) | 0.46428 (8) | 0.2671 (2) | 0.0297 (4) | |
H9A | 0.0748 | 0.4394 | 0.2244 | 0.045* | |
H9B | 0.1866 | 0.4656 | 0.3876 | 0.045* | |
H9C | 0.3049 | 0.4432 | 0.2328 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0191 (2) | 0.0174 (2) | 0.0173 (2) | 0.00059 (15) | −0.00127 (15) | 0.00110 (14) |
S2 | 0.0168 (2) | 0.0145 (2) | 0.0225 (2) | −0.00014 (14) | −0.00308 (15) | 0.00002 (14) |
O1 | 0.0297 (7) | 0.0259 (7) | 0.0335 (7) | −0.0118 (5) | 0.0004 (5) | 0.0025 (5) |
O2 | 0.0259 (6) | 0.0306 (7) | 0.0253 (6) | −0.0021 (5) | 0.0078 (5) | −0.0032 (5) |
O3 | 0.0357 (7) | 0.0235 (6) | 0.0243 (6) | −0.0020 (5) | 0.0034 (5) | 0.0068 (5) |
O4 | 0.0219 (6) | 0.0263 (6) | 0.0278 (6) | 0.0009 (5) | −0.0085 (5) | −0.0014 (5) |
O5 | 0.0154 (5) | 0.0256 (6) | 0.0355 (7) | 0.0006 (5) | −0.0006 (5) | −0.0029 (5) |
O6 | 0.0306 (6) | 0.0227 (6) | 0.0229 (6) | −0.0026 (5) | −0.0038 (5) | −0.0019 (5) |
N1 | 0.0133 (6) | 0.0201 (7) | 0.0220 (7) | 0.0000 (5) | 0.0017 (5) | −0.0045 (5) |
N2 | 0.0202 (7) | 0.0214 (7) | 0.0170 (6) | −0.0029 (6) | −0.0020 (5) | 0.0039 (5) |
C1 | 0.0219 (8) | 0.0258 (9) | 0.0212 (8) | −0.0041 (7) | 0.0045 (7) | −0.0030 (7) |
C2 | 0.0193 (8) | 0.0362 (10) | 0.0275 (9) | 0.0001 (7) | 0.0048 (7) | −0.0101 (8) |
C3 | 0.0233 (8) | 0.0263 (9) | 0.0335 (9) | 0.0064 (7) | −0.0038 (7) | −0.0122 (7) |
C4 | 0.0253 (8) | 0.0194 (8) | 0.0266 (8) | −0.0001 (7) | −0.0053 (7) | −0.0040 (7) |
C5 | 0.0168 (7) | 0.0212 (8) | 0.0145 (7) | −0.0020 (6) | −0.0020 (6) | −0.0016 (6) |
C6 | 0.0185 (8) | 0.0186 (8) | 0.0145 (7) | 0.0006 (6) | 0.0002 (6) | −0.0026 (6) |
C8 | 0.0164 (8) | 0.0332 (10) | 0.0336 (9) | 0.0025 (7) | 0.0063 (7) | −0.0085 (8) |
C9 | 0.0372 (10) | 0.0156 (8) | 0.0356 (10) | −0.0030 (7) | −0.0075 (8) | 0.0044 (7) |
S1—O4 | 1.4242 (12) | C1—H1A | 0.9500 |
S1—O3 | 1.4299 (12) | C2—C3 | 1.381 (3) |
S1—N1 | 1.6650 (13) | C2—H2A | 0.9500 |
S1—C6 | 1.7829 (16) | C3—C4 | 1.385 (3) |
S2—O5 | 1.4222 (12) | C3—H3B | 0.9500 |
S2—O6 | 1.4300 (13) | C4—C5 | 1.380 (2) |
S2—N1 | 1.6721 (14) | C4—H4B | 0.9500 |
S2—C9 | 1.7556 (17) | C5—C6 | 1.398 (2) |
O1—N2 | 1.2241 (18) | C8—H8A | 0.9800 |
O2—N2 | 1.2254 (18) | C8—H8B | 0.9800 |
N1—C8 | 1.484 (2) | C8—H8C | 0.9800 |
N2—C5 | 1.470 (2) | C9—H9A | 0.9800 |
C1—C2 | 1.386 (2) | C9—H9B | 0.9800 |
C1—C6 | 1.390 (2) | C9—H9C | 0.9800 |
O4—S1—O3 | 119.31 (8) | C2—C3—C4 | 120.33 (16) |
O4—S1—N1 | 106.45 (7) | C2—C3—H3B | 119.8 |
O3—S1—N1 | 108.38 (7) | C4—C3—H3B | 119.8 |
O4—S1—C6 | 108.32 (7) | C5—C4—C3 | 119.24 (16) |
O3—S1—C6 | 106.16 (7) | C5—C4—H4B | 120.4 |
N1—S1—C6 | 107.76 (7) | C3—C4—H4B | 120.4 |
O5—S2—O6 | 119.90 (8) | C4—C5—C6 | 121.63 (15) |
O5—S2—N1 | 106.62 (7) | C4—C5—N2 | 115.69 (14) |
O6—S2—N1 | 105.17 (7) | C6—C5—N2 | 122.66 (14) |
O5—S2—C9 | 109.29 (9) | C1—C6—C5 | 117.90 (14) |
O6—S2—C9 | 108.90 (8) | C1—C6—S1 | 116.20 (12) |
N1—S2—C9 | 106.05 (8) | C5—C6—S1 | 125.17 (12) |
C8—N1—S1 | 119.72 (11) | N1—C8—H8A | 109.5 |
C8—N1—S2 | 117.96 (11) | N1—C8—H8B | 109.5 |
S1—N1—S2 | 119.86 (8) | H8A—C8—H8B | 109.5 |
O1—N2—O2 | 124.33 (14) | N1—C8—H8C | 109.5 |
O1—N2—C5 | 117.86 (13) | H8A—C8—H8C | 109.5 |
O2—N2—C5 | 117.75 (13) | H8B—C8—H8C | 109.5 |
C2—C1—C6 | 120.88 (16) | S2—C9—H9A | 109.5 |
C2—C1—H1A | 119.6 | S2—C9—H9B | 109.5 |
C6—C1—H1A | 119.6 | H9A—C9—H9B | 109.5 |
C3—C2—C1 | 119.99 (16) | S2—C9—H9C | 109.5 |
C3—C2—H2A | 120.0 | H9A—C9—H9C | 109.5 |
C1—C2—H2A | 120.0 | H9B—C9—H9C | 109.5 |
O4—S1—N1—C8 | 8.06 (14) | O1—N2—C5—C4 | 34.0 (2) |
O3—S1—N1—C8 | −121.44 (13) | O2—N2—C5—C4 | −143.33 (15) |
C6—S1—N1—C8 | 124.08 (13) | O1—N2—C5—C6 | −147.77 (15) |
O4—S1—N1—S2 | 169.91 (9) | O2—N2—C5—C6 | 34.9 (2) |
O3—S1—N1—S2 | 40.41 (11) | C2—C1—C6—C5 | −0.4 (2) |
C6—S1—N1—S2 | −74.08 (10) | C2—C1—C6—S1 | 170.38 (13) |
O5—S2—N1—C8 | −163.93 (12) | C4—C5—C6—C1 | 1.6 (2) |
O6—S2—N1—C8 | −35.62 (14) | N2—C5—C6—C1 | −176.56 (13) |
C9—S2—N1—C8 | 79.67 (14) | C4—C5—C6—S1 | −168.26 (12) |
O5—S2—N1—S1 | 33.91 (11) | N2—C5—C6—S1 | 13.6 (2) |
O6—S2—N1—S1 | 162.22 (8) | O4—S1—C6—C1 | −139.46 (12) |
C9—S2—N1—S1 | −82.49 (11) | O3—S1—C6—C1 | −10.20 (14) |
C6—C1—C2—C3 | −0.9 (3) | N1—S1—C6—C1 | 105.75 (13) |
C1—C2—C3—C4 | 1.1 (3) | O4—S1—C6—C5 | 30.54 (15) |
C2—C3—C4—C5 | 0.1 (3) | O3—S1—C6—C5 | 159.80 (13) |
C3—C4—C5—C6 | −1.4 (2) | N1—S1—C6—C5 | −84.25 (14) |
C3—C4—C5—N2 | 176.82 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O3 | 0.95 | 2.40 | 2.807 (2) | 106 |
C8—H8A···O4 | 0.98 | 2.30 | 2.811 (2) | 112 |
C9—H9B···O3 | 0.98 | 2.60 | 3.243 (2) | 124 |
C2—H2A···O2i | 0.95 | 2.58 | 3.435 (2) | 149 |
C4—H4B···O6ii | 0.95 | 2.52 | 3.261 (2) | 135 |
C8—H8A···O5iii | 0.98 | 2.50 | 3.194 (2) | 128 |
Symmetry codes: (i) x−1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C8H10N2O6S2 |
Mr | 294.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 153 |
a, b, c (Å) | 6.9540 (14), 20.492 (4), 8.1272 (16) |
β (°) | 92.53 (3) |
V (Å3) | 1157.0 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.48 |
Crystal size (mm) | 0.44 × 0.23 × 0.12 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP area-detector |
Absorption correction | Multi-scan (ABSCOR; Higashi 1995) |
Tmin, Tmax | 0.818, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9002, 2040, 1937 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.065, 1.08 |
No. of reflections | 2040 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.32 |
Computer programs: RAPID-AUTO (Rigaku, 2004), RAPID-AUTO, SHELXTL (Sheldrick, 2001), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O3 | 0.95 | 2.40 | 2.807 (2) | 105.5 |
C8—H8A···O4 | 0.98 | 2.30 | 2.811 (2) | 111.6 |
C9—H9B···O3 | 0.98 | 2.60 | 3.243 (2) | 123.5 |
C2—H2A···O2i | 0.95 | 2.58 | 3.435 (2) | 149.3 |
C4—H4B···O6ii | 0.95 | 2.52 | 3.261 (2) | 134.8 |
C8—H8A···O5iii | 0.98 | 2.50 | 3.194 (2) | 127.6 |
Symmetry codes: (i) x−1, −y+3/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) x+1, y, z. |
Many compounds containing sulfonimide groups possess a broad spectrum of biological activities and can be widely used as herbicides (Kamoshita et al., 1987). Their use as catalysts is also reported (Zhang et al., 2007). Here, we report the synthesis and crystal structure of the title compound.
In the title compound (Fig. 1), all bond lengths and angles are normal (Allen et al., 1987) and in good agreement with those reported previously for similar molecules (Henschel et al., 1996). The molecular structure is stabilized by intramolecular C—H···O hydrogen bonds involving the oxygen atoms bound to atom S1 (Table 1). In the crystal structure (Fig. 2), molecules are linked into a three-dimensional network by weak intermolecular C—H···O hydrogen bonds and aromatic π-π stacking interactions (Cg···Cgi = 4.078 (2) Å; Cg is the centroid of the C1—C6 benzene ring; symmetry code: (i) x, 3/2 - y, -1/2 + z).