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organic compounds
2-[2-(Methylsulfonyl)ethyl]isoindoline-1,3-dione
aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
*Correspondence e-mail: yaocheng@njut.edu.cn
In the molecule of the title compound, C11H11NO4S, the isoindoline ring system is almost planar with a maximum deviation of 0.008 (3)Å. In the intermolecular C—H⋯O interactions link the molecules into a three-dimensional network. π–π contacts between the isoindoline rings [centroid–centroid distances = 3.592 (1) and 3.727 (1) Å] may further stabilize the structure.
Related literature
For a related structure, see: Kilburn et al. (2007). For bond-length data, see: Allen et al. (1987
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995
); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997
); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009
).
Supporting information
10.1107/S160053680902580X/hk2730sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053680902580X/hk2730Isup2.hkl
The title compound was prepared according to the literature method (Kilburn et al., 2007). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (0.1 g) in acetone (25 ml) and evaporating the solvent slowly at room temperature for about 7 d.
H atoms were positioned geometrically with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C11H11NO4S | F(000) = 528 |
Mr = 253.27 | Dx = 1.497 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 7.6030 (15) Å | θ = 9–13° |
b = 17.766 (4) Å | µ = 0.29 mm−1 |
c = 8.9940 (18) Å | T = 294 K |
β = 112.31 (3)° | Block, colorless |
V = 1123.9 (5) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1567 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.3°, θmin = 2.3° |
ω/2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→21 |
Tmin = 0.944, Tmax = 0.972 | l = −10→9 |
2182 measured reflections | 3 standard reflections every 120 min |
2027 independent reflections | intensity decay: 1% |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.09P)2] where P = (Fo2 + 2Fc2)/3 |
2027 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C11H11NO4S | V = 1123.9 (5) Å3 |
Mr = 253.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.6030 (15) Å | µ = 0.29 mm−1 |
b = 17.766 (4) Å | T = 294 K |
c = 8.9940 (18) Å | 0.20 × 0.10 × 0.10 mm |
β = 112.31 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1567 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.030 |
Tmin = 0.944, Tmax = 0.972 | 3 standard reflections every 120 min |
2182 measured reflections | intensity decay: 1% |
2027 independent reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.23 e Å−3 |
2027 reflections | Δρmin = −0.35 e Å−3 |
154 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 | ||
S | 0.44021 (11) | 0.29490 (4) | 0.03299 (8) | 0.0425 (3) | |
O1 | 0.8805 (3) | 0.29528 (10) | 0.4407 (3) | 0.0524 (6) | |
O2 | 0.7221 (3) | 0.50798 (11) | 0.1325 (3) | 0.0555 (6) | |
O3 | 0.3992 (4) | 0.33791 (14) | 0.1503 (3) | 0.0700 (7) | |
O4 | 0.5068 (4) | 0.21958 (12) | 0.0776 (3) | 0.0662 (7) | |
N | 0.8004 (3) | 0.39124 (12) | 0.2541 (3) | 0.0394 (6) | |
C1 | 0.7239 (5) | 0.55296 (19) | 0.6247 (4) | 0.0582 (9) | |
H1A | 0.6981 | 0.5972 | 0.6679 | 0.070* | |
C2 | 0.7703 (5) | 0.4883 (2) | 0.7187 (4) | 0.0584 (9) | |
H2A | 0.7765 | 0.4901 | 0.8239 | 0.070* | |
C3 | 0.8074 (4) | 0.42096 (18) | 0.6577 (4) | 0.0496 (8) | |
H3A | 0.8368 | 0.3774 | 0.7197 | 0.060* | |
C4 | 0.7993 (4) | 0.42102 (15) | 0.5027 (3) | 0.0397 (7) | |
C5 | 0.8318 (4) | 0.35948 (15) | 0.4035 (3) | 0.0390 (6) | |
C6 | 0.7531 (4) | 0.46788 (15) | 0.2484 (3) | 0.0398 (7) | |
C7 | 0.7534 (4) | 0.48617 (15) | 0.4094 (3) | 0.0399 (7) | |
C8 | 0.7155 (4) | 0.55292 (16) | 0.4690 (4) | 0.0495 (8) | |
H8A | 0.6854 | 0.5963 | 0.4066 | 0.059* | |
C9 | 0.8028 (4) | 0.34924 (16) | 0.1157 (3) | 0.0447 (7) | |
H9A | 0.8480 | 0.2986 | 0.1496 | 0.054* | |
H9B | 0.8919 | 0.3730 | 0.0766 | 0.054* | |
C10 | 0.6092 (4) | 0.34476 (15) | −0.0211 (3) | 0.0399 (7) | |
H10A | 0.6228 | 0.3201 | −0.1123 | 0.048* | |
H10B | 0.5626 | 0.3954 | −0.0538 | 0.048* | |
C11 | 0.2381 (5) | 0.29295 (18) | −0.1438 (4) | 0.0541 (8) | |
H11A | 0.1381 | 0.2665 | −0.1253 | 0.081* | |
H11B | 0.2668 | 0.2677 | −0.2263 | 0.081* | |
H11C | 0.1978 | 0.3435 | −0.1773 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0537 (5) | 0.0383 (4) | 0.0401 (4) | −0.0056 (3) | 0.0229 (3) | −0.0007 (3) |
O1 | 0.0670 (15) | 0.0347 (12) | 0.0607 (13) | 0.0102 (10) | 0.0302 (11) | 0.0087 (9) |
O2 | 0.0708 (16) | 0.0379 (11) | 0.0535 (13) | 0.0018 (10) | 0.0189 (11) | 0.0063 (10) |
O3 | 0.0893 (18) | 0.0790 (17) | 0.0613 (14) | −0.0205 (14) | 0.0507 (14) | −0.0248 (12) |
O4 | 0.0747 (17) | 0.0441 (13) | 0.0763 (16) | −0.0027 (11) | 0.0248 (13) | 0.0196 (11) |
N | 0.0463 (14) | 0.0293 (12) | 0.0421 (13) | 0.0008 (10) | 0.0161 (11) | −0.0030 (9) |
C1 | 0.053 (2) | 0.0501 (19) | 0.077 (2) | −0.0085 (15) | 0.0302 (18) | −0.0260 (18) |
C2 | 0.054 (2) | 0.072 (2) | 0.057 (2) | −0.0098 (17) | 0.0289 (16) | −0.0198 (17) |
C3 | 0.0470 (18) | 0.0546 (19) | 0.0502 (18) | −0.0024 (14) | 0.0219 (14) | 0.0019 (14) |
C4 | 0.0328 (15) | 0.0393 (15) | 0.0475 (16) | −0.0028 (11) | 0.0158 (13) | −0.0039 (12) |
C5 | 0.0365 (15) | 0.0337 (15) | 0.0458 (16) | −0.0012 (12) | 0.0147 (12) | 0.0020 (12) |
C6 | 0.0378 (15) | 0.0293 (14) | 0.0483 (16) | −0.0010 (12) | 0.0117 (13) | −0.0003 (12) |
C7 | 0.0336 (14) | 0.0344 (15) | 0.0515 (17) | −0.0033 (12) | 0.0159 (13) | −0.0065 (12) |
C8 | 0.0469 (18) | 0.0367 (16) | 0.064 (2) | −0.0022 (13) | 0.0199 (15) | −0.0097 (14) |
C9 | 0.0505 (18) | 0.0384 (16) | 0.0490 (17) | 0.0016 (13) | 0.0231 (14) | −0.0025 (12) |
C10 | 0.0516 (17) | 0.0323 (14) | 0.0404 (15) | −0.0016 (12) | 0.0227 (13) | 0.0002 (11) |
C11 | 0.052 (2) | 0.057 (2) | 0.0540 (18) | −0.0038 (15) | 0.0208 (16) | 0.0012 (15) |
S—O3 | 1.430 (2) | C3—H3A | 0.9300 |
S—O4 | 1.433 (2) | C4—C7 | 1.394 (4) |
S—C11 | 1.743 (3) | C4—C5 | 1.490 (4) |
S—C10 | 1.774 (3) | C6—C7 | 1.483 (4) |
O1—C5 | 1.207 (3) | C7—C8 | 1.376 (4) |
N—C5 | 1.392 (3) | C8—H8A | 0.9300 |
N—C6 | 1.404 (3) | C9—C10 | 1.520 (4) |
N—C9 | 1.457 (3) | C9—H9A | 0.9700 |
C1—C8 | 1.377 (5) | C9—H9B | 0.9700 |
C1—C2 | 1.391 (5) | C10—H10A | 0.9700 |
C1—H1A | 0.9300 | C10—H10B | 0.9700 |
O2—C6 | 1.210 (3) | C11—H11A | 0.9600 |
C2—C3 | 1.389 (4) | C11—H11B | 0.9600 |
C2—H2A | 0.9300 | C11—H11C | 0.9600 |
C3—C4 | 1.371 (4) | ||
O3—S—O4 | 116.42 (16) | N—C6—C7 | 105.8 (2) |
O3—S—C10 | 108.61 (14) | C8—C7—C4 | 121.5 (3) |
O3—S—C11 | 108.68 (16) | C8—C7—C6 | 130.2 (3) |
O4—S—C10 | 109.11 (14) | C4—C7—C6 | 108.2 (2) |
O4—S—C11 | 109.42 (15) | C7—C8—C1 | 117.4 (3) |
C11—S—C10 | 103.86 (15) | C7—C8—H8A | 121.3 |
C5—N—C6 | 112.1 (2) | C1—C8—H8A | 121.3 |
C5—N—C9 | 124.3 (2) | N—C9—C10 | 113.3 (2) |
C6—N—C9 | 123.5 (2) | N—C9—H9A | 108.9 |
C8—C1—C2 | 121.4 (3) | C10—C9—H9A | 108.9 |
C8—C1—H1A | 119.3 | N—C9—H9B | 108.9 |
C2—C1—H1A | 119.3 | C10—C9—H9B | 108.9 |
C3—C2—C1 | 120.9 (3) | H9A—C9—H9B | 107.7 |
C3—C2—H2A | 119.5 | C9—C10—S | 112.58 (19) |
C1—C2—H2A | 119.5 | C9—C10—H10A | 109.1 |
C4—C3—C2 | 117.6 (3) | S—C10—H10A | 109.1 |
C4—C3—H3A | 121.2 | C9—C10—H10B | 109.1 |
C2—C3—H3A | 121.2 | S—C10—H10B | 109.1 |
C3—C4—C7 | 121.1 (3) | H10A—C10—H10B | 107.8 |
C3—C4—C5 | 130.9 (3) | S—C11—H11A | 109.5 |
C7—C4—C5 | 108.0 (2) | S—C11—H11B | 109.5 |
O1—C5—N | 124.9 (3) | H11A—C11—H11B | 109.5 |
O1—C5—C4 | 129.1 (3) | S—C11—H11C | 109.5 |
N—C5—C4 | 105.9 (2) | H11A—C11—H11C | 109.5 |
O2—C6—N | 124.4 (3) | H11B—C11—H11C | 109.5 |
O2—C6—C7 | 129.8 (3) | ||
C8—C1—C2—C3 | −0.8 (5) | C5—C4—C7—C8 | −179.9 (3) |
C1—C2—C3—C4 | 0.9 (5) | C3—C4—C7—C6 | −179.1 (3) |
C2—C3—C4—C7 | −0.6 (4) | C5—C4—C7—C6 | 0.7 (3) |
C2—C3—C4—C5 | 179.7 (3) | O2—C6—C7—C8 | 1.3 (5) |
C6—N—C5—O1 | −177.4 (3) | N—C6—C7—C8 | −179.5 (3) |
C9—N—C5—O1 | 6.6 (4) | O2—C6—C7—C4 | −179.4 (3) |
C6—N—C5—C4 | 0.8 (3) | N—C6—C7—C4 | −0.2 (3) |
C9—N—C5—C4 | −175.2 (2) | C4—C7—C8—C1 | −0.2 (4) |
C3—C4—C5—O1 | −3.1 (5) | C6—C7—C8—C1 | 179.0 (3) |
C7—C4—C5—O1 | 177.2 (3) | C2—C1—C8—C7 | 0.5 (5) |
C3—C4—C5—N | 178.8 (3) | C5—N—C9—C10 | 112.9 (3) |
C7—C4—C5—N | −0.9 (3) | C6—N—C9—C10 | −62.6 (3) |
C5—N—C6—O2 | 178.9 (3) | N—C9—C10—S | −63.7 (3) |
C9—N—C6—O2 | −5.1 (4) | O3—S—C10—C9 | 67.7 (2) |
C5—N—C6—C7 | −0.4 (3) | O4—S—C10—C9 | −60.2 (2) |
C9—N—C6—C7 | 175.6 (2) | C11—S—C10—C9 | −176.8 (2) |
C3—C4—C7—C8 | 0.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O3i | 0.93 | 2.34 | 3.189 (5) | 152 |
C11—H11A···O1ii | 0.96 | 2.51 | 3.463 (4) | 175 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H11NO4S |
Mr | 253.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 7.6030 (15), 17.766 (4), 8.9940 (18) |
β (°) | 112.31 (3) |
V (Å3) | 1123.9 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.944, 0.972 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2182, 2027, 1567 |
Rint | 0.030 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.144, 1.01 |
No. of reflections | 2027 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.35 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O3i | 0.93 | 2.34 | 3.189 (5) | 152 |
C11—H11A···O1ii | 0.96 | 2.51 | 3.463 (4) | 175 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, −y+1/2, z−1/2. |
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Kilburn, J. P., Andersen, H. S., Kampen, G. C. T. & Ebdrup, S. (2007). PCT Int. Appl. WO 2007051811. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound is an important pharmaceutical intermediate, which is used in treatment of metabolic syndrome. As part of our studies in this area, we report herein the crystal structure of the title compound.
In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (N/C4-C7) and B (C1-C4/C7/C8) are, of course, planar and the dihedral angle between them is A/B = 0.61 (3)°. The isoindoline ring system is planar with a maximum deviation of -0.008 (3) Å for atom N.
In the crystal structure, intermolecular C-H···O interactions (Table 1) link the molecules into a three-dimensional network, in which they may be effective in the stabilization of the structure. The π–π contacts between the isoindoline rings, Cg1—Cg2i and Cg2—Cg2ii [symmetry codes: (i) 2 - x, -y, 2 - z, (ii) 1 - x, -y, 2 - z, where Cg1 and Cg2 are centroids of the rings A (N/C4-C7) and B (C1-C4/C7/C8), respectively] may further stabilize the structure, with centroid-centroid distances of 3.592 (1) and 3.727 (1) Å, respectively.