(3R,3aS,6aR)-2,5-Dimethyl-3-(5-phenyl-2-thien­yl)perhydro­pyrrolo[3,4-d][1,2]oxazole-4,6-dione

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

doi:10.1107/S1600536808020102

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages o1423-o1424

doi:10.1107/S1600536808020102

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(3R,3aS,6aR)-2,5-Dimethyl-3-(5-phenyl-2-thienyl)perhydropyrrolo[3,4-d][1,2]oxazole-4,6-dione

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

^aDepartment of Chemistry, Faculty of Arts and Sciences, Mehmet Akif Ersoy University, TR-15030 Burdur, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Gazi University, Ankara, Turkey, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 27 June 2008; accepted 1 July 2008; online 5 July 2008)

The crystal structure of the title compound, C₁₇H₁₆N₂O₃S, exhibits intramolecular C—H⋯S and intermolecular C—H⋯S and C—H⋯O hydrogen bonds, C—S⋯N [S⋯N = 3.033 (2) Å and C—S⋯N = 142.76 (9)°] interactions, and C—H⋯π interactions; these interactions generate S(4), S(6) and R₂²(14) ring motifs. The isoxazole ring adopts an envelope conformation, with the N atom displaced by 0.672 (2) Å from the plane of the other ring atoms. The thiophene ring is oriented with respect to the succinimide and phenyl rings at dihedral angles of 40.03 (12) and 5.21 (13)°, respectively. The dihedral angle between the succinimide and phenyl rings is 39.38 (12)°.

Related literature

For general background, see: Huisgen (1960 ); Black et al. (1975 ); Richman (2001 ); De Clercq (2002 ); Donadas et al. (2004 ); Merino et al. (2003 ); Chiacchio et al. (2003 ); Iannazzo et al. (2002 ). For related literature, see: Heaney et al. (2001 ). For ring motif details, see: Bernstein et al. (1995 ); Etter (1990 ).

Experimental

Crystal data

C₁₇H₁₆N₂O₃S
M_r = 328.38
Orthorhombic, P n a 2₁
a = 12.7768 (7) Å
b = 10.9803 (6) Å
c = 11.1069 (9) Å
V = 1558.22 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.65 × 0.46 × 0.27 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.889, T_max = 0.935
6395 measured reflections
3332 independent reflections
2899 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.099
S = 1.04
3332 reflections
221 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1451 Friedel pairs
Flack parameter = −0.13 (8)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the S1/C7–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯S1	0.93	2.68	3.097 (3)	108
C8—H8⋯S1ⁱ	0.93	3.00	3.887 (2)	160
C14—H14B⋯O2ⁱ	0.96	2.65	3.417 (4)	137
C13—H13⋯Cg1ⁱⁱ	1.01 (3)	2.96 (3)	3.875 (2)	152 (2)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[-x, -y, z-{\script{1\over 2}}]$ .

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/S1600536808020102/hk2484sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020102/hk2484Isup2.hkl

checkCIF report

Comment top

A general principle for the synthesis of five-membered rings was introduced in 1960 as 1,3-dipolar cycloaddition and turned out to be remarkably widespread (Huisgen, 1960, 1961). Because of easy 1,3-dipolar cycloaddition reactions to alkenes, alkynes, isocyanates, isothiocyanates, phospharanes, sulphenes and sulphynl compounds; nitrones are the important intermediates in synthetic organic chemistry (Black et al., 1975). There has been an ever-increasing quest for modified nucleosides, due to their potential applications in antiviral and anticancer therapies (Richman, 2001; De Clercq, 2002; Donadas et al., 2004). In a recent approach to modified nucleosides, the furanose ring has been replaced by other heterocyclic analogs (Merino et al., 2003). Among these N and O containing heterocycles have emerged as important candidates, and have been shown to display useful anticancer and antiviral properties (Chiacchio et al., 2003; Iannazzo et al., 2002). The present work is part of a structural study of compounds of substited 2,5-dimethyl-4-(thiophen-2-yl)-tetrahydropyrrolo[3,4 -c]pyrrole-1,\3(2H,3aH)-dione systems with hydrogen-bond donors, and we report herein the crystal structure of the title compound, (I).

The overall view and atom-labelling of the molecule of (I) are displayed in Fig. 1. The thiophene ring is oriented with respect to succinimide and phenyl rings at dihedral angles of 40.03 (12)° and 5.21 (13)°, respectively. The dihedral angle between succinimide and phenyl rings is 39.38 (12)°. The isoxazole ring has envelope conformation, with N1 atom displaced by -0.672 (2) Å from the plane of the other ring atoms.

The hydrogen-bonding parameters are given in Table 1 and the packing arrangements of the molecules are illustrated in Figs. 2 and 3. Compound is stabilized by intramolecular C—H···S hydrogen bond and S···N heteroatom interactions [in C1—S1···N; S···N = 3.033 (2) Å, C1—S1···N = 142.76 (9) °], which form S(4) and S(6) motifs, and intermolecular C—H···S and C—H···O hydrogen bonds and C—H···π interactions. As shown in Fig. 2 the structure of the compound is made up of C8—H8···S1 and C14—H14B···O2 H-bonded polymeric bands of [C₁₂H₁₄N₂O₃S] molecules, which are nearly elongated along [100]. These polymeric chains are linked to each other and generate R₂²(14) ring motifs (Bernstein et al., 1995; Etter, 1990). The crystal packing is also stabilized by C13—H13···Cg1 interactions (Fig. 3, Table 1).

Related literature top

For general background, see: Huisgen (1960, 1961); Black et al. (1975); Richman (2001); De Clercq (2002); Donadas et al. (2004); Merino et al. (2003); Chiacchio et al. (2003); Iannazzo et al. (2002). For related literature, see: Heaney et al. (2001). For ring motif details, see: Bernstein et al. (1995); Etter (1990).

Experimental top

N-Methyl-C-(-5-Phenylthiophen) nitrone, (II), was prepared from 5-Phenylthiophenecarbaldehyde, N-methyl-hydroxylamine hydrochloride and sodium carbonate in CH₂Cl₂ according to the literature method (Heaney et al., 2001). For the preparation of the title compound, (II) (657 mg, 3 mmol) and N-methylmaleimide (370 mg, 3.3 mmol) were dissolved in benzene (50 ml). The reaction mixture was refluxed for 12 h, and monitored by TLC. After evaporation of the solvent, the reaction mixture was separated by column chromatography, using the mixture of petroleum ether/ethyl acetate (2:1) as the eluant. The cis-isomer, (I), was recrystallized from CHCl₃/n-hexane (mp: 452,9-454,4 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. Displacement ellipsoids are drawn at the 20% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A partial packing diagram of (I), showing the formation of S(4), S(6) and R₂²(14) ring motifs along [100] [symmetry code: (i) x - 1/2, y, z]. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 3. A packing diagram of (I) [symmetry code: (i) 1 - x, 1 - y, -z], where Cg1 is the centroid of ring (S1/C7-C10). Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

(3R,3aS,6aR)-2,5-Dimethyl-3-(5-phenyl-2- thienyl)perhydropyrrolo[3,4-d][1,2]oxazole-4,6-dione top

Crystal data top

C₁₇H₁₆N₂O₃S	F(000) = 688
M_r = 328.38	D_x = 1.400 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6395 reflections
a = 12.7768 (7) Å	θ = 1.8–28.0°
b = 10.9803 (6) Å	µ = 0.22 mm⁻¹
c = 11.1069 (9) Å	T = 296 K
V = 1558.22 (17) Å³	Prism, colorless
Z = 4	0.65 × 0.46 × 0.27 mm

Data collection top

Stoe IPDSII diffractometer	3332 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2899 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.051
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.5°, θ_min = 2.5°
ω scan rotation method	h = −13→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→14
T_min = 0.889, T_max = 0.935	l = −12→14
6395 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0659P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.099	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.22 e Å⁻³
3332 reflections	Δρ_min = −0.22 e Å⁻³
221 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0122 (17)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.13 (8)

Crystal data top

C₁₇H₁₆N₂O₃S	V = 1558.22 (17) Å³
M_r = 328.38	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 12.7768 (7) Å	µ = 0.22 mm⁻¹
b = 10.9803 (6) Å	T = 296 K
c = 11.1069 (9) Å	0.65 × 0.46 × 0.27 mm

Data collection top

Stoe IPDSII diffractometer	3332 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2899 reflections with I > 2σ(I)
T_min = 0.889, T_max = 0.935	R_int = 0.051
6395 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.099	Δρ_max = 0.22 e Å⁻³
S = 1.04	Δρ_min = −0.22 e Å⁻³
3332 reflections	Absolute structure: Flack (1983)
221 parameters	Absolute structure parameter: −0.13 (8)
1 restraint

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.64659 (16)	0.19809 (17)	0.66560 (19)	0.0427 (4)
C2	0.7443 (2)	0.1782 (2)	0.7188 (2)	0.0585 (6)
H2	0.8048	0.1938	0.6749	0.070*
C3	0.7523 (2)	0.1360 (3)	0.8346 (3)	0.0701 (7)
H3	0.8181	0.1227	0.8680	0.084*
C4	0.6641 (3)	0.1132 (3)	0.9022 (3)	0.0721 (8)
H4	0.6696	0.0857	0.9811	0.087*
C5	0.5678 (2)	0.1320 (3)	0.8504 (2)	0.0731 (8)
H5	0.5075	0.1163	0.8948	0.088*
C6	0.55911 (19)	0.1738 (2)	0.7341 (2)	0.0593 (6)
H6	0.4930	0.1857	0.7011	0.071*
C7	0.63920 (16)	0.24233 (18)	0.5415 (2)	0.0411 (4)
C8	0.71619 (15)	0.2782 (2)	0.4653 (3)	0.0530 (5)
H8	0.7866	0.2789	0.4864	0.064*
C9	0.67952 (15)	0.3144 (2)	0.3508 (2)	0.0511 (5)
H9	0.7236	0.3398	0.2891	0.061*
C10	0.57421 (14)	0.30882 (18)	0.33939 (19)	0.0409 (4)
C11	0.50963 (15)	0.3425 (2)	0.23306 (19)	0.0432 (4)
C12	0.46103 (16)	0.4708 (2)	0.22929 (19)	0.0458 (4)
C13	0.36143 (17)	0.4492 (2)	0.15649 (19)	0.0473 (5)
C14	0.4393 (2)	0.1435 (2)	0.1799 (2)	0.0589 (6)
H14A	0.3761	0.0963	0.1764	0.088*
H14B	0.4884	0.1044	0.2327	0.088*
H14C	0.4690	0.1498	0.1007	0.088*
C15	0.42400 (17)	0.51840 (19)	0.3496 (2)	0.0490 (5)
C16	0.27329 (17)	0.4855 (2)	0.2411 (2)	0.0506 (5)
C17	0.2543 (2)	0.5584 (3)	0.4516 (3)	0.0716 (8)
H17A	0.2708	0.6414	0.4711	0.086*
H17B	0.2700	0.5072	0.5192	0.086*
H17C	0.1812	0.5520	0.4326	0.086*
N1	0.41573 (13)	0.26461 (15)	0.22512 (15)	0.0419 (4)
N2	0.31576 (15)	0.52026 (17)	0.34890 (18)	0.0504 (4)
O1	0.47725 (15)	0.55117 (17)	0.43306 (17)	0.0690 (5)
O2	0.18093 (14)	0.48473 (19)	0.2184 (2)	0.0786 (6)
O3	0.35719 (12)	0.32333 (14)	0.12785 (14)	0.0506 (4)
S1	0.51891 (3)	0.25445 (5)	0.47066 (6)	0.04736 (14)
H11	0.5520 (18)	0.3385 (19)	0.161 (2)	0.038 (5)*
H12	0.511 (2)	0.535 (3)	0.191 (3)	0.068 (8)*
H13	0.356 (2)	0.494 (3)	0.079 (3)	0.064 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0437 (10)	0.0377 (9)	0.0468 (11)	0.0072 (8)	−0.0082 (8)	−0.0047 (8)
C2	0.0489 (11)	0.0677 (15)	0.0590 (14)	0.0064 (10)	−0.0144 (11)	0.0013 (11)
C3	0.0682 (16)	0.0798 (17)	0.0622 (16)	0.0142 (13)	−0.0284 (14)	−0.0017 (13)
C4	0.085 (2)	0.0832 (17)	0.0478 (14)	0.0131 (15)	−0.0162 (13)	0.0040 (12)
C5	0.0745 (18)	0.096 (2)	0.0489 (14)	0.0006 (14)	0.0033 (14)	0.0095 (13)
C6	0.0491 (13)	0.0780 (16)	0.0508 (13)	0.0091 (10)	−0.0068 (10)	0.0064 (11)
C7	0.0322 (9)	0.0409 (9)	0.0501 (12)	0.0039 (8)	−0.0056 (8)	−0.0030 (7)
C8	0.0282 (8)	0.0666 (13)	0.0643 (13)	0.0027 (8)	−0.0018 (11)	0.0054 (14)
C9	0.0299 (9)	0.0670 (13)	0.0564 (12)	0.0011 (9)	0.0055 (9)	0.0079 (10)
C10	0.0305 (8)	0.0497 (10)	0.0426 (10)	0.0005 (7)	0.0039 (8)	0.0012 (8)
C11	0.0339 (9)	0.0595 (11)	0.0361 (9)	−0.0023 (8)	0.0046 (8)	0.0052 (8)
C12	0.0392 (9)	0.0555 (11)	0.0428 (10)	−0.0083 (9)	−0.0024 (8)	0.0111 (9)
C13	0.0448 (10)	0.0572 (11)	0.0398 (11)	−0.0034 (9)	−0.0074 (8)	0.0106 (8)
C14	0.0554 (13)	0.0613 (13)	0.0600 (14)	0.0043 (10)	−0.0034 (11)	−0.0127 (10)
C15	0.0496 (11)	0.0466 (10)	0.0507 (11)	0.0009 (9)	−0.0084 (10)	0.0050 (8)
C16	0.0437 (12)	0.0522 (11)	0.0559 (14)	−0.0022 (8)	−0.0037 (9)	0.0045 (9)
C17	0.0770 (17)	0.0676 (15)	0.0704 (19)	0.0072 (12)	0.0215 (14)	−0.0051 (13)
N1	0.0374 (8)	0.0523 (9)	0.0361 (8)	−0.0025 (7)	−0.0026 (6)	−0.0002 (7)
N2	0.0497 (10)	0.0516 (9)	0.0499 (10)	−0.0011 (8)	0.0039 (9)	0.0046 (7)
O1	0.0711 (12)	0.0742 (11)	0.0618 (11)	0.0082 (9)	−0.0242 (9)	−0.0139 (9)
O2	0.0387 (9)	0.0955 (13)	0.1016 (16)	0.0011 (8)	−0.0111 (9)	−0.0080 (12)
O3	0.0506 (9)	0.0618 (9)	0.0394 (7)	−0.0024 (7)	−0.0121 (6)	0.0002 (6)
S1	0.0287 (2)	0.0711 (3)	0.0423 (2)	−0.0033 (2)	−0.0012 (2)	0.0108 (2)

Geometric parameters (Å, º) top

C1—C6	1.378 (3)	C11—C12	1.540 (3)
C1—C2	1.398 (3)	C11—H11	0.97 (2)
C1—C7	1.464 (3)	C12—C15	1.511 (3)
C2—C3	1.371 (4)	C12—C13	1.526 (3)
C2—H2	0.9300	C12—H12	1.04 (3)
C3—C4	1.377 (5)	C13—O3	1.419 (3)
C3—H3	0.9300	C13—C16	1.520 (3)
C4—C5	1.374 (4)	C13—H13	1.00 (3)
C4—H4	0.9300	C14—N1	1.453 (3)
C5—C6	1.375 (4)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—H6	0.9300	C14—H14C	0.9600
C7—C8	1.357 (3)	C15—O1	1.205 (3)
C7—S1	1.732 (2)	C15—N2	1.383 (3)
C8—C9	1.412 (4)	C16—O2	1.207 (3)
C8—H8	0.9300	C16—N2	1.369 (3)
C9—C10	1.353 (3)	C17—N2	1.447 (3)
C9—H9	0.9300	C17—H17A	0.9600
C10—C11	1.487 (3)	C17—H17B	0.9600
C10—S1	1.727 (2)	C17—H17C	0.9600
C11—N1	1.476 (3)	N1—O3	1.464 (2)

C6—C1—C2	117.4 (2)	C15—C12—C11	114.73 (17)
C6—C1—C7	122.11 (19)	C13—C12—C11	102.00 (17)
C2—C1—C7	120.5 (2)	C15—C12—H12	108.7 (15)
C3—C2—C1	121.1 (3)	C13—C12—H12	113.7 (15)
C3—C2—H2	119.5	C11—C12—H12	112.3 (16)
C1—C2—H2	119.5	O3—C13—C16	111.44 (18)
C2—C3—C4	120.8 (2)	O3—C13—C12	107.59 (17)
C2—C3—H3	119.6	C16—C13—C12	104.45 (18)
C4—C3—H3	119.6	O3—C13—H13	106.8 (16)
C5—C4—C3	118.5 (3)	C16—C13—H13	110.9 (17)
C5—C4—H4	120.7	C12—C13—H13	115.7 (17)
C3—C4—H4	120.7	N1—C14—H14A	109.5
C4—C5—C6	121.0 (3)	N1—C14—H14B	109.5
C4—C5—H5	119.5	H14A—C14—H14B	109.5
C6—C5—H5	119.5	N1—C14—H14C	109.5
C5—C6—C1	121.2 (2)	H14A—C14—H14C	109.5
C5—C6—H6	119.4	H14B—C14—H14C	109.5
C1—C6—H6	119.4	O1—C15—N2	124.4 (2)
C8—C7—C1	129.6 (2)	O1—C15—C12	127.4 (2)
C8—C7—S1	109.71 (17)	N2—C15—C12	108.27 (18)
C1—C7—S1	120.70 (16)	O2—C16—N2	124.9 (2)
C7—C8—C9	113.79 (18)	O2—C16—C13	126.4 (2)
C7—C8—H8	123.1	N2—C16—C13	108.67 (18)
C9—C8—H8	123.1	N2—C17—H17A	109.5
C10—C9—C8	113.7 (2)	N2—C17—H17B	109.5
C10—C9—H9	123.2	H17A—C17—H17B	109.5
C8—C9—H9	123.2	N2—C17—H17C	109.5
C9—C10—C11	127.94 (19)	H17A—C17—H17C	109.5
C9—C10—S1	110.08 (16)	H17B—C17—H17C	109.5
C11—C10—S1	121.97 (13)	C14—N1—O3	104.71 (16)
N1—C11—C10	110.73 (16)	C14—N1—C11	112.49 (17)
N1—C11—C12	101.59 (15)	O3—N1—C11	101.78 (14)
C10—C11—C12	118.22 (18)	C16—N2—C15	113.39 (19)
N1—C11—H11	112.3 (13)	C16—N2—C17	123.7 (2)
C10—C11—H11	109.5 (14)	C15—N2—C17	122.9 (2)
C12—C11—H11	104.2 (13)	C13—O3—N1	104.13 (14)
C15—C12—C13	105.14 (18)	C10—S1—C7	92.71 (10)

C6—C1—C2—C3	0.0 (3)	C13—C12—C15—O1	−177.3 (2)
C7—C1—C2—C3	−179.6 (2)	C11—C12—C15—O1	71.5 (3)
C1—C2—C3—C4	−0.6 (4)	C13—C12—C15—N2	1.9 (2)
C2—C3—C4—C5	0.9 (4)	C11—C12—C15—N2	−109.3 (2)
C3—C4—C5—C6	−0.6 (5)	O3—C13—C16—O2	−65.7 (3)
C4—C5—C6—C1	0.0 (4)	C12—C13—C16—O2	178.4 (2)
C2—C1—C6—C5	0.3 (4)	O3—C13—C16—N2	114.50 (19)
C7—C1—C6—C5	179.9 (2)	C12—C13—C16—N2	−1.4 (2)
C6—C1—C7—C8	175.0 (2)	C10—C11—N1—C14	−76.4 (2)
C2—C1—C7—C8	−5.4 (3)	C12—C11—N1—C14	157.21 (18)
C6—C1—C7—S1	−5.3 (3)	C10—C11—N1—O3	172.10 (16)
C2—C1—C7—S1	174.28 (17)	C12—C11—N1—O3	45.68 (17)
C1—C7—C8—C9	179.4 (2)	O2—C16—N2—C15	−177.0 (2)
S1—C7—C8—C9	−0.4 (3)	C13—C16—N2—C15	2.8 (3)
C7—C8—C9—C10	1.2 (3)	O2—C16—N2—C17	1.5 (4)
C8—C9—C10—C11	178.6 (2)	C13—C16—N2—C17	−178.8 (2)
C8—C9—C10—S1	−1.4 (3)	O1—C15—N2—C16	176.2 (2)
C9—C10—C11—N1	147.6 (2)	C12—C15—N2—C16	−3.0 (3)
S1—C10—C11—N1	−32.4 (2)	O1—C15—N2—C17	−2.2 (4)
C9—C10—C11—C12	−95.9 (3)	C12—C15—N2—C17	178.5 (2)
S1—C10—C11—C12	84.2 (2)	C16—C13—O3—N1	−86.75 (19)
N1—C11—C12—C15	84.5 (2)	C12—C13—O3—N1	27.2 (2)
C10—C11—C12—C15	−36.9 (3)	C14—N1—O3—C13	−163.37 (17)
N1—C11—C12—C13	−28.59 (19)	C11—N1—O3—C13	−46.07 (19)
C10—C11—C12—C13	−149.94 (17)	C9—C10—S1—C7	1.06 (18)
C15—C12—C13—O3	−118.85 (18)	C11—C10—S1—C7	−178.96 (17)
C11—C12—C13—O3	1.2 (2)	C8—C7—S1—C10	−0.40 (17)
C15—C12—C13—C16	−0.3 (2)	C1—C7—S1—C10	179.86 (16)
C11—C12—C13—C16	119.74 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···S1	0.93	2.69	3.100 (2)	108
C8—H8···S1ⁱ	0.93	3.00	3.887 (2)	160
C14—H14B···O2ⁱ	0.96	2.65	3.417 (4)	137
C13—H13···Cg1ⁱⁱ	1.00 (3)	2.97 (3)	3.876 (2)	151 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O₃S
M_r	328.38
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	296
a, b, c (Å)	12.7768 (7), 10.9803 (6), 11.1069 (9)
V (Å³)	1558.22 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.65 × 0.46 × 0.27

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.889, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	6395, 3332, 2899
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 1.04
No. of reflections	3332
No. of parameters	221
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22
Absolute structure	Flack (1983)
Absolute structure parameter	−0.13 (8)

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
C6—H6···S1	0.93	2.69	3.100 (2)	108
C8—H8···S1ⁱ	0.93	3.00	3.887 (2)	160.4
C14—H14B···O2ⁱ	0.96	2.65	3.417 (4)	137.2
C13—H13···Cg1ⁱⁱ	1.00 (3)	2.97 (3)	3.876 (2)	151 (2)

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

References

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Volume 64| Part 8| August 2008| Pages o1423-o1424

doi:10.1107/S1600536808020102

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

(3R,3aS,6aR)-2,5-Di­methyl-3-(5-phenyl-2-thien­yl)perhydro­pyrrolo[3,4-d][1,2]oxazole-4,6-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3R,3aS,6aR)-2,5-Dimethyl-3-(5-phenyl-2-thienyl)perhydropyrrolo[3,4-d][1,2]oxazole-4,6-dione