2-[2-(Methyl­sulfon­yl)eth­yl]isoindoline-1,3-dione

Tang, Q.; Feng, Q.; Xu, J.; Yao, C.

doi:10.1107/S160053680902580X

organic compounds

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Volume 65| Part 8| August 2009| Page o1932

doi:10.1107/S160053680902580X

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2-[2-(Methylsulfonyl)ethyl]isoindoline-1,3-dione

Qiong Tang,^a Qi Feng,^a Jian Xu ^a and Cheng Yao ^a ^*

^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

(Received 28 June 2009; accepted 3 July 2009; online 18 July 2009)

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 crystal structure, 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

C₁₁H₁₁NO₄S
M_r = 253.27
Monoclinic, P 2₁ /c
a = 7.6030 (15) Å
b = 17.766 (4) Å
c = 8.9940 (18) Å
β = 112.31 (3)°
V = 1123.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 294 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.944, T_max = 0.972
2182 measured reflections
2027 independent reflections
1567 reflections with I > 2σ(I)
R_int = 0.030
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.144
S = 1.01
2027 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: 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

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902580X/hk2730sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902580X/hk2730Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

For a related structure, see: Kilburn et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

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.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: 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).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.

2-[2-(Methylsulfonyl)ethyl]isoindoline-1,3-dione top

Crystal data top

C₁₁H₁₁NO₄S	F(000) = 528
M_r = 253.27	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	1567 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 25.3°, θ_min = 2.3°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→21
T_min = 0.944, T_max = 0.972	l = −10→9
2182 measured reflections	3 standard reflections every 120 min
2027 independent reflections	intensity decay: 1%

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.09P)²] where P = (F_o² + 2F_c²)/3
2027 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₁H₁₁NO₄S	V = 1123.9 (5) Å³
M_r = 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)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1567 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.030
T_min = 0.944, T_max = 0.972	3 standard reflections every 120 min
2182 measured reflections	intensity decay: 1%
2027 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.01	Δρ_max = 0.23 e Å⁻³
2027 reflections	Δρ_min = −0.35 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.944, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	2182, 2027, 1567
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

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