2,5-Dimethyl-3-(3-methyl-thio-phen-2-yl)perhydro-pyrrolo[3,4-d]isoxazole-4,6-dione.

The crystal structure of the title compound, C(12)H(14)N(2)O(3)S, exhibits intra-molecular C-H⋯S and inter-molecular C-H⋯S, C-H⋯O hydrogen bonds, C-S⋯N [S⋯N = 2.980 (2) Å, C-S⋯N = 145.78 (17)°] and C-H⋯π inter-actions; these inter-actions generate two C(5) chains and S(4), S(6) and R(4) (4)(28) ring motifs. The isoxazole ring has an envelope conformation; the N atom, which is the flap atom, is displaced by 0.261 (2) Å from the plane defined by the remaining four atoms. The dihedral angle between the succinimide and thio-phene rings is 46.8 (2)°.

Related literature

For general background, see: Huisgen (1960 ▶); Black et al. (1975 ▶); Alibes et al. (2003 ▶); Kumar et al. (2003 ▶); Richman (2001 ▶); Chiacchio et al. (2003a ▶,b ▶). For ring motif details, see: Etter (1990 ▶); Bernstein et al. (1995 ▶). For related literature, see: Malamidou-Xenikaki et al. (1997 ▶); Coutouli-Argyropoulou et al. (1997 ▶); De Clercq (2002a ▶,b ▶,c ▶).

Experimental

Crystal data

C12H14N2O3S

M = 266.31

Orthorhombic,

a = 12.0318 (10) Å

b = 14.6759 (9) Å

c = 7.2635 (4) Å

V = 1282.57 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 (2) K

0.52 × 0.48 × 0.43 mm

Data collection

STOE IPDS2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.895, T max = 0.929

12725 measured reflections

2511 independent reflections

2212 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.090

S = 1.08

2511 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), 1151 Friedel pairs

Flack parameter: 0.01 (9)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012993/gw2041sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012993/gw2041Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H14N2O3S	F(000) = 560
Mr = 266.31	Dx = 1.379 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 12725 reflections
a = 12.0318 (10) Å	θ = 1.7–28.0°
b = 14.6759 (9) Å	µ = 0.25 mm−1
c = 7.2635 (4) Å	T = 296 K
V = 1282.57 (15) Å3	Block, colorless
Z = 4	0.52 × 0.48 × 0.43 mm

STOE IPDS2 diffractometer	2511 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2212 reflections with I > 2σ(I)
plane graphite	Rint = 0.058
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.2°
w–scan rotation method	h = −14→14
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −18→18
Tmin = 0.895, Tmax = 0.929	l = −8→8
12725 measured reflections

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.1351P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2511 reflections	Δρmax = 0.19 e Å−3
177 parameters	Δρmin = −0.16 e Å−3
1 restraint	Absolute structure: Flack (1983), 1151 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (9)

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
C1	0.76496 (19)	0.41201 (15)	0.2036 (3)	0.0359 (5)
C2	0.8126 (2)	0.40438 (19)	0.0347 (4)	0.0543 (7)
C3	0.9305 (2)	0.4061 (2)	0.0477 (5)	0.0651 (9)
H3	0.9768	0.4008	−0.0543	0.078*
C4	0.9688 (2)	0.41604 (19)	0.2179 (5)	0.0622 (8)
H4	1.0438	0.4198	0.2479	0.075*
C5	0.7496 (4)	0.3958 (3)	−0.1384 (4)	0.1026 (14)
H5A	0.6863	0.4356	−0.1349	0.103*
H5B	0.7249	0.3340	−0.1529	0.103*
H5C	0.7964	0.4122	−0.2401	0.103*
C6	0.64389 (18)	0.41050 (16)	0.2458 (3)	0.0369 (5)
C7	0.6216 (2)	0.54462 (18)	0.4463 (4)	0.0608 (7)
H7A	0.6049	0.5621	0.5707	0.061*
H7B	0.5670	0.5701	0.3648	0.061*
H7C	0.6939	0.5668	0.4133	0.061*
C8	0.5012 (2)	0.32778 (16)	0.4027 (4)	0.0477 (6)
C9	0.5415 (2)	0.26963 (18)	0.5620 (4)	0.0523 (6)
C10	0.6628 (2)	0.24093 (17)	0.3249 (4)	0.0482 (7)
C11	0.5881 (2)	0.31489 (17)	0.2531 (4)	0.0441 (5)
C12	0.6924 (3)	0.1569 (2)	0.6175 (6)	0.0829 (10)
H12A	0.6583	0.1543	0.7369	0.083*
H12B	0.7685	0.1756	0.6301	0.083*
H12C	0.6895	0.0978	0.5611	0.083*
N1	0.61980 (15)	0.44503 (14)	0.4315 (3)	0.0409 (5)
N2	0.63330 (18)	0.22216 (14)	0.5031 (4)	0.0546 (6)
O1	0.50134 (14)	0.42160 (11)	0.4512 (3)	0.0543 (5)
O2	0.5015 (2)	0.26507 (16)	0.7130 (3)	0.0813 (7)
O3	0.73562 (16)	0.20182 (14)	0.2435 (4)	0.0697 (6)
S1	0.86334 (5)	0.42104 (5)	0.37501 (8)	0.05480 (19)
H6	0.6036 (19)	0.4459 (14)	0.160 (3)	0.028 (5)*
H8	0.432 (2)	0.3135 (15)	0.374 (4)	0.045 (6)*
H11	0.561 (2)	0.2974 (15)	0.130 (4)	0.037 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0367 (12)	0.0340 (11)	0.0370 (11)	−0.0006 (9)	0.0001 (9)	0.0022 (9)
C2	0.0608 (16)	0.0580 (16)	0.0442 (15)	−0.0081 (13)	0.0116 (13)	−0.0019 (12)
C3	0.0514 (16)	0.0625 (18)	0.082 (2)	−0.0035 (14)	0.0339 (17)	−0.0026 (16)
C4	0.0357 (14)	0.0555 (17)	0.096 (2)	0.0034 (12)	0.0073 (14)	0.0085 (17)
C5	0.109 (3)	0.151 (4)	0.0478 (17)	−0.020 (3)	0.011 (2)	−0.020 (2)
C6	0.0326 (11)	0.0403 (12)	0.0378 (11)	0.0036 (10)	−0.0012 (10)	0.0071 (10)
C7	0.0629 (17)	0.0447 (14)	0.0747 (18)	0.0046 (13)	0.0221 (14)	−0.0023 (13)
C8	0.0284 (11)	0.0511 (15)	0.0634 (18)	−0.0013 (10)	0.0011 (12)	0.0058 (12)
C9	0.0459 (13)	0.0448 (14)	0.0664 (17)	−0.0075 (12)	0.0057 (13)	0.0077 (12)
C10	0.0356 (12)	0.0355 (13)	0.0735 (18)	−0.0046 (10)	−0.0001 (11)	−0.0017 (11)
C11	0.0344 (11)	0.0462 (14)	0.0517 (15)	−0.0007 (10)	−0.0063 (11)	−0.0006 (11)
C12	0.082 (2)	0.061 (2)	0.106 (3)	0.0089 (17)	−0.010 (2)	0.036 (2)
N1	0.0343 (10)	0.0412 (10)	0.0472 (11)	0.0010 (8)	0.0110 (8)	0.0021 (8)
N2	0.0481 (13)	0.0400 (11)	0.0758 (16)	−0.0013 (9)	−0.0049 (11)	0.0138 (11)
O1	0.0368 (9)	0.0461 (9)	0.0800 (12)	0.0083 (7)	0.0194 (8)	0.0056 (9)
O2	0.0908 (17)	0.0780 (15)	0.0750 (14)	0.0003 (13)	0.0242 (13)	0.0235 (13)
O3	0.0463 (11)	0.0520 (11)	0.1108 (16)	0.0067 (9)	0.0152 (12)	−0.0069 (11)
S1	0.0411 (3)	0.0754 (4)	0.0479 (3)	−0.0001 (3)	−0.0090 (3)	0.0068 (4)

C1—C2	1.358 (3)	C7—H7B	0.9600
C1—C6	1.489 (3)	C7—H7C	0.9600
C1—S1	1.723 (2)	C8—O1	1.421 (3)
C2—C3	1.422 (4)	C8—C9	1.517 (4)
C2—C5	1.474 (4)	C8—C11	1.519 (4)
C3—C4	1.328 (5)	C8—H8	0.88 (3)
C3—H3	0.9300	C9—O2	1.200 (3)
C4—S1	1.708 (3)	C9—N2	1.374 (4)
C4—H4	0.9300	C10—O3	1.202 (3)
C5—H5A	0.9600	C10—N2	1.371 (4)
C5—H5B	0.9600	C10—C11	1.503 (4)
C5—H5C	0.9600	C11—H11	0.99 (3)
C6—N1	1.470 (3)	C12—N2	1.454 (4)
C6—C11	1.556 (3)	C12—H12A	0.9600
C6—H6	0.95 (2)	C12—H12B	0.9600
C7—N1	1.466 (3)	C12—H12C	0.9600
C7—H7A	0.9600	N1—O1	1.473 (2)
C2—C1—C6	126.7 (2)	O1—C8—C11	107.29 (19)
C2—C1—S1	111.65 (19)	C9—C8—C11	104.8 (2)
C6—C1—S1	121.65 (16)	O1—C8—H8	106.9 (15)
C1—C2—C3	111.1 (2)	C9—C8—H8	110.5 (17)
C1—C2—C5	124.1 (3)	C11—C8—H8	116.6 (19)
C3—C2—C5	124.8 (3)	O2—C9—N2	125.4 (3)
C4—C3—C2	114.2 (3)	O2—C9—C8	126.9 (3)
C4—C3—H3	122.9	N2—C9—C8	107.8 (2)
C2—C3—H3	122.9	O3—C10—N2	123.9 (3)
C3—C4—S1	111.6 (2)	O3—C10—C11	127.6 (3)
C3—C4—H4	124.2	N2—C10—C11	108.5 (2)
S1—C4—H4	124.2	C10—C11—C8	104.7 (2)
C2—C5—H5A	109.5	C10—C11—C6	113.9 (2)
C2—C5—H5B	109.5	C8—C11—C6	102.1 (2)
H5A—C5—H5B	109.5	C10—C11—H11	108.9 (14)
C2—C5—H5C	109.5	C8—C11—H11	117.1 (15)
H5A—C5—H5C	109.5	C6—C11—H11	110.3 (14)
H5B—C5—H5C	109.5	N2—C12—H12A	109.5
N1—C6—C1	112.12 (19)	N2—C12—H12B	109.5
N1—C6—C11	101.21 (19)	H12A—C12—H12B	109.5
C1—C6—C11	116.27 (19)	N2—C12—H12C	109.5
N1—C6—H6	108.4 (13)	H12A—C12—H12C	109.5
C1—C6—H6	110.9 (14)	H12B—C12—H12C	109.5
C11—C6—H6	107.2 (13)	C7—N1—C6	114.11 (19)
N1—C7—H7A	109.5	C7—N1—O1	103.87 (18)
N1—C7—H7B	109.5	C6—N1—O1	101.51 (17)
H7A—C7—H7B	109.5	C10—N2—C9	113.6 (2)
N1—C7—H7C	109.5	C10—N2—C12	123.1 (3)
H7A—C7—H7C	109.5	C9—N2—C12	123.3 (3)
H7B—C7—H7C	109.5	C8—O1—N1	101.71 (16)
O1—C8—C9	110.8 (2)	C4—S1—C1	91.40 (14)
C6—C1—C2—C3	−178.3 (2)	N1—C6—C11—C10	−88.1 (2)
S1—C1—C2—C3	−0.1 (3)	C1—C6—C11—C10	33.7 (3)
C6—C1—C2—C5	1.9 (5)	N1—C6—C11—C8	24.1 (2)
S1—C1—C2—C5	−179.9 (3)	C1—C6—C11—C8	145.9 (2)
C1—C2—C3—C4	−1.0 (4)	C1—C6—N1—C7	78.5 (3)
C5—C2—C3—C4	178.8 (3)	C11—C6—N1—C7	−156.9 (2)
C2—C3—C4—S1	1.5 (4)	C1—C6—N1—O1	−170.41 (17)
C2—C1—C6—N1	−164.3 (2)	C11—C6—N1—O1	−45.82 (19)
S1—C1—C6—N1	17.6 (3)	O3—C10—N2—C9	−174.5 (3)
C2—C1—C6—C11	79.9 (3)	C11—C10—N2—C9	4.2 (3)
S1—C1—C6—C11	−98.2 (2)	O3—C10—N2—C12	4.5 (4)
O1—C8—C9—O2	59.0 (4)	C11—C10—N2—C12	−176.8 (3)
C11—C8—C9—O2	174.4 (3)	O2—C9—N2—C10	−179.0 (3)
O1—C8—C9—N2	−121.1 (2)	C8—C9—N2—C10	1.0 (3)
C11—C8—C9—N2	−5.6 (3)	O2—C9—N2—C12	2.0 (5)
O3—C10—C11—C8	171.1 (2)	C8—C9—N2—C12	−177.9 (3)
N2—C10—C11—C8	−7.5 (3)	C9—C8—O1—N1	78.9 (2)
O3—C10—C11—C6	−78.2 (3)	C11—C8—O1—N1	−34.9 (2)
N2—C10—C11—C6	103.1 (2)	C7—N1—O1—C8	169.8 (2)
O1—C8—C11—C10	125.6 (2)	C6—N1—O1—C8	51.1 (2)
C9—C8—C11—C10	7.7 (3)	C3—C4—S1—C1	−1.3 (2)
O1—C8—C11—C6	6.7 (2)	C2—C1—S1—C4	0.8 (2)
C9—C8—C11—C6	−111.2 (2)	C6—C1—S1—C4	179.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7C···S1	0.96	2.97	3.467 (3)	114.
C5—H5C···S1i	0.96	2.91	3.808 (3)	156.
C8—H8···O3ii	0.88 (2)	2.56 (2)	3.426 (3)	168 (2)
C12—H12C···Cg1iii	0.96	2.94	3.693 (3)	137.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7C⋯S1	0.96	2.97	3.467 (3)	114
C5—H5C⋯S1i	0.96	2.91	3.808 (3)	156
C8—H8⋯O3ii	0.88 (2)	2.56 (2)	3.426 (3)	168 (2)
C12—H12C⋯Cg1iii	0.96	2.94	3.693 (3)	137

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the S1,C1–C4 ring.