2-Methyl-3-(5-methyl-2-thien­yl)-5-phenyl­perhydro­pyrrolo[3,4-d]isoxazole-4,6-dione

Odabaşoğlu, M.; Özkan, H.; Yıldırır, Y.; Büyükgüngör, O.

doi:10.1107/S1600536809009209

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o862-o863

doi:10.1107/S1600536809009209

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2-Methyl-3-(5-methyl-2-thienyl)-5-phenylperhydropyrrolo[3,4-d]isoxazole-4,6-dione

Mustafa Odabaşoğlu,^a Hamdi Özkan,^b Yılmaz Yıldırır ^c and Orhan Büyükgüngör ^d ^*

^aPamukkale University, Denizli Higher Vocational School, Chemistry Program, TR-20159 Kınıklı, Denizli, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Science, Kırıkkale University, Kırıkkale, Turkey, ^cDepartment of Chemistry, Faculty of Arts and Science, Gazi University, Ankara, Turkey, and ^dDepartment of Physics, Faculty of Arts and Science, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 26 February 2009; accepted 12 March 2009; online 25 March 2009)

In the molecule of the title compound, C₁₇H₁₆N₂O₃S, the phenyl ring is oriented with respect to the thiophene and succinimide rings at dihedral angles of 88.08 (3) and 57.81 (3)°, respectively; the dihedral angle between the thiophene and succinimide rings is 35.69 (3)°. The isoxazole ring adopts an envelope conformation with the N atom at the flap position. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into infinite chains along the b axis. Weak C—H⋯π interactions may further stabilize the structure.

Related literature

For nitrones as versatile synthetic intermediates in organic synthesis, see: Black et al. (1975 ); Banerji & Sahu (1986 ); Torsell (1988 ); Banerji & Basu (1992 ). For nitrones as a convenient class of compounds for the syntheses of ultimate carcinogens, see: Mallesha, Ravikumar, Mantelingu et al. (2001 ); Mallesha, Ravikumar & Rangappa (2001 ). For the 1,3-dipolar cycloaddition reaction of nitrones with alkenes in the preparation of isoxazolidines, see: Tufariello (1984 ). For isoxazolidines in the synthesis of β-lactams, see: Padwa et al. (1981 , 1984 ). For the use of β-lactams to treat bacterial infections, see: Ochiai et al. (1967 ); as natural products, see: Baldwin & Aube (1987 ); as versatile synthetic intermediates, see: Padwa (1984 ). For the preparation of C-(5-Methyl-2-thienyl)-N-methylnitrone used in the synthesis, see: Heaney et al. (2001 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₆N₂O₃S
M_r = 328.38
Monoclinic, P 2₁ /c
a = 12.6558 (5) Å
b = 8.5738 (3) Å
c = 19.3824 (8) Å
β = 128.654 (3)°
V = 1642.42 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.73 × 0.52 × 0.26 mm

Data collection

STOE IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.685, T_max = 0.946
19464 measured reflections
3401 independent reflections
2872 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.098
S = 1.05
3401 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H18⋯O2ⁱ	0.94 (2)	2.41 (2)	3.103 (2)	130
C2—H2⋯Cg1ⁱⁱ	0.93	2.99	3.83 (2)	152 (1)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y-1, z. Cg1 is the centroid of the S1/C13–C16 ring.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009209/hk2634sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009209/hk2634Isup2.hkl

checkCIF report

Comment top

1,3-Dipolar cycloaddition reaction of nitrones to olefins is of synthetic interest. In the present work, isoxazolidines have been synthesized in high yield via intermolecular cycloaddition of N-arylnitrone with monosubstituted olefins and are employed for biological evaluation. Nitrones are versatile synthetic intermediates in organic synthesis (Black et al., 1975; Banerji & Sahu, 1986; Torsell, 1988; Banerji & Basu, 1992). Recently, they reported that nitrones are a convenient class of compounds for the syntheses of ultimate carcinogens (Mallesha, Ravikumar, Mantelingu et al., 2001); Mallesha, Ravikumar & Rangappa, 2001), which are biologically interesting molecules. The 1,3-dipolar cycloaddition reaction of nitrones with alkenes is an important method for preparing isoxazolidines in a regioselective and stereoselective manner (Tufariello, 1984). These isoxazolidines are used in the syntheses of β-lactams (Padwa et al., 1981; Padwa et al., 1984) which are of value in the treatment of bacterial infections (Ochiai et al., 1967), occur as natural products (Baldwin & Aube, 1987), serve as versatile synthetic intermediates (Padwa, 1984), and are biologically interesting compounds (Ochiai et al., 1967). In view of the interest shown in these compounds, 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 (C1-C6), B (N1/C7-C10) and D (S1/C13-C16) are, of course, planar, and they are oriented at dihedral angles of A/B = 57.81 (3), A/D = 88.08 (3) and B/D = 35.69 (3) °. Ring C (O3/N2/C8/C9/C11) adopts envelope conformation with N2 atom displaced by 0.736 (3) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2) into infinite chains along the b-axis, in which they may be effective in the stabilization of the structure. The weak C—H···π interaction (Table 1) may further stabilize the structure.

Related literature top

For general background, see: Black et al. (1975); Banerji & Sahu (1986); Torsell (1988); Banerji & Basu (1992); Mallesha, Ravikumar, Mantelingu et al. (2001); Mallesha, Ravikumar & Rangappa (2001); Tufariello (1984); Padwa et al. (1981, 1984); Ochiai et al. (1967); Baldwin & Aube (1987); Padwa (1984). For bond-length data, see: Allen et al. (1987).

For related literature, see: Heaney et al. (2001).

Experimental top

C-(5-Methyl-2-thienyl)-N-methylnitrone was prepared from 5-methylthiophene-2 -carbaldehyde, N-methyl-hydroxylamine hydrochloride and sodium carbonate in CH₂Cl₂ (Scheme 2) according to the literature method (Heaney et al., 2001). For the preparation of the title compound, C-(5-methyl-2-thienyl)-N -methylnitrone (471 mg, 3 mmol) and N-phenylmaleimide (570 mg, 3.3 mmol) were dissolved in benzene (50 ml). The reaction mixture was refluxed for 12 h, and monitored by TLC (Scheme 2). After evaporation of the solvent, the reaction mixture was separated by column chromatography, using mixtures of petroleum ether and ethyl acetate (1:2) as the eluant. The trans-isomer, was recrystallized from CHCl₃/n-hexane (1:3) in 2 d (m.p. 425-428 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
	Fig. 2. A partial packing diagram of the title compound [symmetry code: (i) 1-x, y+1/2, z]. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
	Fig. 3. The formation of the title compound.

2-Methyl-3-(5-methyl-2-thienyl)-5-phenylperhydropyrrolo[3,4-d]isoxazole- 4,6-dione top

Crystal data top

C₁₇H₁₆N₂O₃S	F(000) = 688
M_r = 328.38	D_x = 1.328 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 19464 reflections
a = 12.6558 (5) Å	θ = 1.6–28.0°
b = 8.5738 (3) Å	µ = 0.21 mm⁻¹
c = 19.3824 (8) Å	T = 296 K
β = 128.654 (3)°	Prism, colorless
V = 1642.42 (13) Å³	0.73 × 0.52 × 0.26 mm
Z = 4

Data collection top

STOE IPDS 2 diffractometer	3401 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2872 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.028
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.1°
ω–scan rotation method	h = −15→15
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
T_min = 0.685, T_max = 0.946	l = −24→24
19464 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0494P)² + 0.2689P] where P = (F_o² + 2F_c²)/3
3401 reflections	(Δ/σ)_max = 0.001
222 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₇H₁₆N₂O₃S	V = 1642.42 (13) Å³
M_r = 328.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.6558 (5) Å	µ = 0.21 mm⁻¹
b = 8.5738 (3) Å	T = 296 K
c = 19.3824 (8) Å	0.73 × 0.52 × 0.26 mm
β = 128.654 (3)°

Data collection top

STOE IPDS 2 diffractometer	3401 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2872 reflections with I > 2σ(I)
T_min = 0.685, T_max = 0.946	R_int = 0.028
19464 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.19 e Å⁻³
3401 reflections	Δρ_min = −0.27 e Å⁻³
222 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
S1	0.31342 (4)	0.24446 (5)	0.79541 (3)	0.06492 (15)
O1	0.18469 (12)	0.56188 (13)	0.50732 (7)	0.0639 (3)
O2	0.42647 (11)	0.86900 (14)	0.75274 (7)	0.0629 (3)
O3	0.28425 (11)	0.60569 (12)	0.76942 (7)	0.0549 (3)
N1	0.30675 (12)	0.74300 (13)	0.61858 (8)	0.0479 (3)
N2	0.14465 (13)	0.58932 (14)	0.68562 (9)	0.0527 (3)
C1	0.29019 (15)	0.87293 (17)	0.56598 (9)	0.0509 (3)
C2	0.2287 (2)	1.0061 (2)	0.56436 (13)	0.0712 (5)
H2	0.1985	1.0126	0.5974	0.085*
C3	0.2120 (3)	1.1305 (2)	0.51308 (15)	0.0896 (7)
H3	0.1707	1.2213	0.5119	0.108*
C4	0.2556 (3)	1.1214 (3)	0.46425 (15)	0.0889 (6)
H4	0.2436	1.2055	0.4297	0.107*
C5	0.3173 (2)	0.9880 (3)	0.46614 (13)	0.0814 (6)
H5	0.3473	0.9821	0.4330	0.098*
C6	0.33513 (17)	0.8621 (2)	0.51722 (11)	0.0628 (4)
H6	0.3768	0.7715	0.5186	0.075*
C7	0.25037 (14)	0.59615 (17)	0.58428 (9)	0.0473 (3)
C8	0.28380 (14)	0.49173 (17)	0.65825 (9)	0.0460 (3)
H18	0.3330 (16)	0.4050 (19)	0.6624 (10)	0.053 (4)*
C9	0.36272 (14)	0.59533 (18)	0.74030 (9)	0.0490 (3)
H20	0.4521 (18)	0.5567 (19)	0.7893 (11)	0.061 (5)*
C10	0.37259 (13)	0.75292 (18)	0.70902 (9)	0.0487 (3)
C11	0.15792 (14)	0.44699 (17)	0.64828 (9)	0.0472 (3)
H19	0.0810 (16)	0.4439 (17)	0.5872 (10)	0.049 (4)*
C12	0.05862 (19)	0.5727 (2)	0.71120 (13)	0.0675 (5)
H12A	0.0615	0.6671	0.7390	0.101*
H12B	0.0905	0.4873	0.7518	0.101*
H12C	−0.0328	0.5527	0.6596	0.101*
C13	0.17079 (14)	0.29515 (17)	0.69109 (9)	0.0490 (3)
C14	0.07838 (16)	0.17956 (19)	0.65756 (11)	0.0585 (4)
H14	−0.0060	0.1843	0.6020	0.070*
C15	0.12214 (19)	0.0503 (2)	0.71510 (13)	0.0654 (4)
H15	0.0695	−0.0383	0.7005	0.079*
C16	0.2461 (2)	0.06732 (18)	0.79239 (11)	0.0611 (4)
C17	0.3246 (3)	−0.0399 (2)	0.87043 (13)	0.0863 (6)
H17A	0.3342	0.0069	0.9191	0.104*
H17B	0.4125	−0.0580	0.8868	0.104*
H17C	0.2774	−0.1372	0.8554	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0661 (3)	0.0518 (2)	0.0513 (2)	−0.00077 (18)	0.0242 (2)	0.00449 (17)
O1	0.0760 (7)	0.0603 (7)	0.0466 (6)	−0.0122 (5)	0.0340 (6)	−0.0086 (5)
O2	0.0621 (6)	0.0689 (7)	0.0590 (6)	−0.0249 (5)	0.0385 (5)	−0.0200 (5)
O3	0.0620 (6)	0.0565 (6)	0.0547 (6)	−0.0088 (5)	0.0406 (5)	−0.0077 (5)
N1	0.0488 (6)	0.0494 (6)	0.0469 (6)	−0.0058 (5)	0.0306 (5)	−0.0050 (5)
N2	0.0511 (7)	0.0495 (7)	0.0634 (7)	0.0039 (5)	0.0386 (6)	0.0026 (6)
C1	0.0514 (8)	0.0511 (8)	0.0498 (8)	−0.0087 (6)	0.0314 (7)	−0.0057 (6)
C2	0.0973 (13)	0.0549 (9)	0.0763 (11)	0.0028 (9)	0.0615 (11)	−0.0019 (8)
C3	0.1285 (19)	0.0525 (10)	0.0891 (14)	0.0070 (11)	0.0685 (14)	0.0019 (10)
C4	0.1185 (18)	0.0681 (12)	0.0788 (13)	−0.0123 (12)	0.0610 (13)	0.0090 (10)
C5	0.0878 (13)	0.0980 (15)	0.0694 (11)	−0.0068 (12)	0.0544 (11)	0.0105 (11)
C6	0.0620 (9)	0.0733 (11)	0.0584 (9)	0.0005 (8)	0.0401 (8)	0.0018 (8)
C7	0.0444 (7)	0.0486 (7)	0.0483 (7)	−0.0017 (6)	0.0286 (6)	−0.0046 (6)
C8	0.0421 (7)	0.0459 (7)	0.0460 (7)	0.0033 (6)	0.0257 (6)	−0.0006 (6)
C9	0.0412 (7)	0.0571 (8)	0.0433 (7)	0.0011 (6)	0.0237 (6)	−0.0017 (6)
C10	0.0391 (6)	0.0587 (8)	0.0482 (7)	−0.0080 (6)	0.0273 (6)	−0.0084 (6)
C11	0.0422 (7)	0.0481 (7)	0.0449 (7)	0.0011 (6)	0.0242 (6)	0.0014 (6)
C12	0.0724 (11)	0.0608 (10)	0.0930 (13)	0.0054 (8)	0.0633 (11)	0.0042 (9)
C13	0.0488 (7)	0.0464 (7)	0.0502 (8)	0.0001 (6)	0.0301 (6)	−0.0006 (6)
C14	0.0538 (8)	0.0563 (9)	0.0629 (9)	−0.0062 (7)	0.0352 (7)	−0.0017 (7)
C15	0.0780 (11)	0.0516 (9)	0.0828 (12)	−0.0090 (8)	0.0581 (10)	−0.0012 (8)
C16	0.0862 (12)	0.0480 (8)	0.0642 (10)	0.0071 (8)	0.0542 (10)	0.0048 (7)
C17	0.1304 (19)	0.0610 (11)	0.0754 (12)	0.0163 (11)	0.0682 (13)	0.0158 (9)

Geometric parameters (Å, º) top

C1—C2	1.371 (2)	C10—O2	1.2049 (18)
C1—C6	1.377 (2)	C10—N1	1.3963 (18)
C1—N1	1.4345 (18)	C11—N2	1.4809 (19)
C2—C3	1.381 (3)	C11—C13	1.497 (2)
C2—H2	0.9300	C11—H19	0.954 (15)
C3—C4	1.363 (3)	C12—N2	1.458 (2)
C3—H3	0.9300	C12—H12A	0.9600
C4—C5	1.372 (3)	C12—H12B	0.9600
C4—H4	0.9300	C12—H12C	0.9600
C5—C6	1.385 (3)	C13—C14	1.350 (2)
C5—H5	0.9300	C13—S1	1.7252 (15)
C6—H6	0.9300	C14—C15	1.417 (2)
C7—O1	1.2056 (17)	C14—H14	0.9300
C7—N1	1.3942 (18)	C15—C16	1.338 (3)
C7—C8	1.509 (2)	C15—H15	0.9300
C8—C9	1.5269 (19)	C16—C17	1.497 (2)
C8—C11	1.529 (2)	C16—S1	1.7243 (17)
C8—H18	0.941 (16)	C17—H17A	0.9600
C9—O3	1.4188 (18)	C17—H17B	0.9600
C9—C10	1.518 (2)	C17—H17C	0.9600
C9—H20	0.974 (17)	N2—O3	1.4813 (16)

C2—C1—C6	120.81 (16)	N2—C11—C8	99.14 (11)
C2—C1—N1	119.46 (14)	C13—C11—C8	113.83 (12)
C6—C1—N1	119.72 (14)	N2—C11—H19	106.8 (9)
C1—C2—C3	119.26 (18)	C13—C11—H19	109.7 (9)
C1—C2—H2	120.4	C8—C11—H19	109.8 (9)
C3—C2—H2	120.4	N2—C12—H12A	109.5
C4—C3—C2	120.6 (2)	N2—C12—H12B	109.5
C4—C3—H3	119.7	H12A—C12—H12B	109.5
C2—C3—H3	119.7	N2—C12—H12C	109.5
C3—C4—C5	119.98 (19)	H12A—C12—H12C	109.5
C3—C4—H4	120.0	H12B—C12—H12C	109.5
C5—C4—H4	120.0	C14—C13—C11	127.58 (14)
C4—C5—C6	120.29 (19)	C14—C13—S1	109.68 (12)
C4—C5—H5	119.9	C11—C13—S1	122.73 (11)
C6—C5—H5	119.9	C13—C14—C15	113.59 (15)
C1—C6—C5	119.05 (17)	C13—C14—H14	123.2
C1—C6—H6	120.5	C15—C14—H14	123.2
C5—C6—H6	120.5	C16—C15—C14	113.85 (15)
O1—C7—N1	124.20 (14)	C16—C15—H15	123.1
O1—C7—C8	126.75 (13)	C14—C15—H15	123.1
N1—C7—C8	109.05 (11)	C15—C16—C17	129.64 (18)
C7—C8—C9	104.90 (12)	C15—C16—S1	110.06 (12)
C7—C8—C11	112.15 (11)	C17—C16—S1	120.29 (16)
C9—C8—C11	103.27 (11)	C16—C17—H17A	109.5
C7—C8—H18	109.1 (10)	C16—C17—H17B	109.5
C9—C8—H18	113.8 (10)	H17A—C17—H17B	109.5
C11—C8—H18	113.2 (10)	C16—C17—H17C	109.5
O3—C9—C10	110.85 (12)	H17A—C17—H17C	109.5
O3—C9—C8	106.60 (11)	H17B—C17—H17C	109.5
C10—C9—C8	105.39 (11)	C7—N1—C10	112.34 (12)
O3—C9—H20	108.0 (10)	C7—N1—C1	123.94 (12)
C10—C9—H20	110.9 (10)	C10—N1—C1	123.56 (12)
C8—C9—H20	115.0 (10)	C12—N2—C11	114.98 (12)
O2—C10—N1	124.40 (14)	C12—N2—O3	105.60 (12)
O2—C10—C9	127.31 (13)	C11—N2—O3	101.08 (10)
N1—C10—C9	108.29 (12)	C9—O3—N2	102.11 (10)
N2—C11—C13	116.88 (12)	C16—S1—C13	92.81 (8)

C6—C1—C2—C3	0.0 (3)	S1—C13—C14—C15	−0.39 (18)
N1—C1—C2—C3	−179.52 (17)	C13—C14—C15—C16	0.8 (2)
C1—C2—C3—C4	0.2 (3)	C14—C15—C16—C17	177.85 (17)
C2—C3—C4—C5	−0.3 (4)	C14—C15—C16—S1	−0.8 (2)
C3—C4—C5—C6	0.3 (3)	O1—C7—N1—C10	177.30 (14)
C2—C1—C6—C5	0.0 (3)	C8—C7—N1—C10	−2.03 (16)
N1—C1—C6—C5	179.42 (15)	O1—C7—N1—C1	1.9 (2)
C4—C5—C6—C1	−0.1 (3)	C8—C7—N1—C1	−177.45 (12)
O1—C7—C8—C9	−177.41 (15)	O2—C10—N1—C7	−178.38 (14)
N1—C7—C8—C9	1.90 (15)	C9—C10—N1—C7	1.26 (15)
O1—C7—C8—C11	−66.0 (2)	O2—C10—N1—C1	−2.9 (2)
N1—C7—C8—C11	113.29 (13)	C9—C10—N1—C1	176.71 (12)
C7—C8—C9—O3	116.74 (12)	C2—C1—N1—C7	119.20 (17)
C11—C8—C9—O3	−0.88 (14)	C6—C1—N1—C7	−60.3 (2)
C7—C8—C9—C10	−1.12 (14)	C2—C1—N1—C10	−55.7 (2)
C11—C8—C9—C10	−118.74 (12)	C6—C1—N1—C10	124.80 (16)
O3—C9—C10—O2	64.68 (19)	C13—C11—N2—C12	−40.09 (18)
C8—C9—C10—O2	179.63 (14)	C8—C11—N2—C12	−162.79 (13)
O3—C9—C10—N1	−114.96 (12)	C13—C11—N2—O3	73.09 (14)
C8—C9—C10—N1	0.00 (15)	C8—C11—N2—O3	−49.61 (12)
C7—C8—C11—N2	−81.54 (13)	C10—C9—O3—N2	84.42 (12)
C9—C8—C11—N2	30.87 (13)	C8—C9—O3—N2	−29.78 (13)
C7—C8—C11—C13	153.59 (12)	C12—N2—O3—C9	170.81 (12)
C9—C8—C11—C13	−93.99 (14)	C11—N2—O3—C9	50.71 (12)
N2—C11—C13—C14	109.49 (18)	C15—C16—S1—C13	0.48 (14)
C8—C11—C13—C14	−135.77 (16)	C17—C16—S1—C13	−178.30 (15)
N2—C11—C13—S1	−70.16 (16)	C14—C13—S1—C16	−0.04 (13)
C8—C11—C13—S1	44.58 (17)	C11—C13—S1—C16	179.67 (13)
C11—C13—C14—C15	179.92 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H18···O2ⁱ	0.94 (2)	2.41 (2)	3.103 (2)	130.0
C2—H2···Cg1ⁱⁱ	0.93	2.99	3.83 (2)	152 (1)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O₃S
M_r	328.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.6558 (5), 8.5738 (3), 19.3824 (8)
β (°)	128.654 (3)
V (Å³)	1642.42 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.73 × 0.52 × 0.26

Data collection
Diffractometer	STOE IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.685, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	19464, 3401, 2872
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.098, 1.05
No. of reflections	3401
No. of parameters	222
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.27

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H18···O2ⁱ	0.94 (2)	2.41 (2)	3.103 (2)	130.0
C2—H2···Cg1ⁱⁱ	0.93	2.99	3.83 (2)	152.0 (2)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, y−1, z.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for use of the Stoe IPDS 2 diffractometer (purchased under grant No. F.279 of the University Research Fund).

References

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Volume 65| Part 4| April 2009| Pages o862-o863

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Methyl-3-(5-methyl-2-thien­yl)-5-phenyl­perhydro­pyrrolo[3,4-d]isoxazole-4,6-dione

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Experimental

Crystal data

Data collection

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References

organic compounds

2-Methyl-3-(5-methyl-2-thienyl)-5-phenylperhydropyrrolo[3,4-d]isoxazole-4,6-dione