(3aR,6S,7aR)-7a-Chloro-6-methyl-2-(4-nitro­phenyl­sulfon­yl)-1,2,3,6,7,7a-hexa­hydro-3a,6-ep­oxy­iso­indole

Demircan, A.; Temel, E.; Kandemir, M.K.; Çolak, M.; Büyükgüngör, O.

doi:10.1107/S1600536813026329

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Pages o1628-o1629

doi:10.1107/S1600536813026329

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(3aR,6S,7aR)-7a-Chloro-6-methyl-2-(4-nitrophenylsulfonyl)-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole

Aydın Demircan,^a Ersin Temel,^b ^* Muhammet Kasım Kandemir,^a Medine Çolak ^a and Orhan Büyükgüngör ^b

^aDepartment of Chemistry, Faculty of Arts and Sciences, Niĝde University, TR-51240 Niĝde, Turkey, and ^bOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, TR-55139 Samsun, Turkey
^*Correspondence e-mail: etemel@omu.edu.tr

(Received 20 September 2013; accepted 23 September 2013; online 9 October 2013)

In the title compound, C₁₅H₁₅ClN₂O₅S, the tetrahydrofuran ring adopts an envelope conformation with the O atom as the flap. The pyrrolidine ring adopts an envelope conformation with the chlorine-substituted C atom as the flap. In the crystal, two types of C—H⋯O hydrogen bonds generate R²₂(20) and R⁴₄(26) rings, with adjacent rings running parallel to ac plane. Further C—H⋯O hydrogen bonds form a C(6) chain, linking the molecules in the b-axis direction.

CCDC reference: 962926

Related literature

For chemical background to protecting groups, see: Greene & Wuts (1999 ); Romanski et al. (2012 ); Chan & White (2004 ); Yasushi & Higuchi (2006 ); Blanc & Bochet (2007 ); Demircan & Parsons (2002 ); Demirtaş et al. (2002 ); Katritzky et al. (2004 ); Merlin et al. (1988 ); Büyükgüngör et al. (2005 ); Koşar et al. (2006a ,b ); Karaarslan et al. (2007 ); Demircan et al. (2011 ); Temel et al. (2011 , 2012 ). For puckering parameters, see: Cremer & Pople, (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₅ClN₂O₅S
M_r = 370.80
Monoclinic, P 2₁ /c
a = 8.6049 (5) Å
b = 7.1949 (3) Å
c = 26.8195 (15) Å
β = 101.186 (4)°
V = 1628.89 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 296 K
0.48 × 0.24 × 0.02 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.894, T_max = 0.992
13941 measured reflections
3449 independent reflections
1564 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.192
S = 0.89
3449 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 1.12 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.93	2.46	3.205 (6)	138
C7—H7A⋯O2ⁱⁱ	0.97	2.51	3.219 (6)	129
C9—H9⋯O4ⁱⁱⁱ	0.93	2.52	3.388 (6)	155
Symmetry codes: (i) x, y-1, z; (ii) -x+2, -y+1, -z+1; (iii) x+1, y, z.

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, 2012 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 962926

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813026329/bt6935sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813026329/bt6935Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813026329/bt6935Isup3.cml

checkCIF report

Comment top

The use of protective groups has been popular in synthetic pathways (Romanski et al., 2012; Chan & White, 2004; Yasushi and Higuchi, 2006; Blanc and Bochet, 2007). Many protective groups have been, developed to block other reactive sites of a molecule like NH, OH, SH, aldehyde etc. They should be easily removable (Greene & Wuts, 1999). Bulky protective groups on nitrogen like tert-butoxy carboxylate (Demircan and Parsons, 2002), the trityl group (Demirtaş et al., 2002), tosyl (Katritzky et al., 2004), mesyl (Merlin et al., 1988) predominates in cycloaddition reactions over relatively small protective groups such as methyl, ethyl groups.

We have been working on intramolecular Diels Alder reaction (IMDAF) of compounds with a furan core using different side chains containing a heteroatom like oxygen, sulfur and nitrogen. Isoindole derivatives have been often synthesized and analyzed in our group using bulky protective groups (Büyükgüngör et al., 2005; Koşar et al., 2006a; Koşar et al., 2006b; Karaarslan et al., 2007; Demircan et al., 2011). Tosyl and mesyl groups have been previously used and reported in a series of sulfonamides (Temel et al., 2012; Temel et al., 2011). We now here report our further finding that cycloadduct, 3 with p-nosyl group was generated at the intermediate via, 2 in aqueous condition without any other solvent system.

The title compound contains epoxyisoindole and phenyl rings linked through N—S—C bridge (Fig. 2). Tetrahydrofuran rings, pyrrolidine ring and six-membered ring that generate epoxyisoindole moiety are puckered. Both tetrahydrofuran rings adopt an envelope conformation with the puckering parameters of Q=0.516 (5) Å, ϕ=182.8 (6)° for O₅/C_8–11 and Q=0.611 (5) Å, ϕ=3.5 (5)° for O₅/C_8,13,12,11, respectively. The other five-membered ring, pyrrolidine, has the puckering parameters of Q=0.288 (5) Å and ϕ=277.2 (9)°. The six-membered ring, C_8–13, has a boat conformation, according to the puckering parameters [Q=0.928 (5) Å, θ=87.5 (3)° and ϕ=180.8 (3)°] (Cremer & Pople, 1975).

The crystal packing of is stabilized by C—H···O hydrogen bonds. While the C7—H7A···O2 hydrogen bonds generate R²₂(20) rings, the combination of C7—H7A···O2 and C9—H9···O4 hydrogen bonds generate R⁴₄(26) rings (Fig. 4). These adjacent rings are running parallel to ac-plane. Additionally, C3—H3···O3 hydrogen bonds forming a C(6) chain link the molecules through b axis (Fig 3) (Bernstein et al. 1995).

Related literature top

For chemical background to protecting groups, see: Greene & Wuts (1999); Romanski et al. (2012); Chan & White (2004); Yasushi & Higuchi (2006); Blanc & Bochet (2007); Demircan & Parsons (2002); Demirtaş et al. (2002); Katritzky et al. (2004); Merlin et al. (1988); Büyükgüngör et al. (2005); Koşar et al. (2006a,b); Karaarslan et al. (2007); Demircan et al. (2011); Temel et al. (2011, 2012). For puckering parameters, see: Cremer & Pople, (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

2-Chloro-N-(furan-2-ylmethyl)prop-2-en-1-amine, 1 (0.32 g, 1.72 mmol) in water (50 ml) was added p-nitrobenzenesulfonyl chloride (0.45 g, 2.06 mmol) portion wise followed by potassium carbonate (0.9 g, 6.45 mol). The reaction mixture was stirred for 48 h at 369 K. Then, the reaction mixture was allowed to warm up to room temperature and NaOH 10% (35 ml) was added. The mixture was then extracted with ethyl acetate (3x35 ml) and brine (35 ml). Combined organic phases were dried over magnesium sulfate, filtered and evaporated. The purification by column chromatography afforded colourless crystals (0.42 g, 66% yield). t.l.c., (Hexane:Ethylacetate); (8:2), Rf: 0.42). Recrystallization was performed in DCM:Hexane. Melting Point: 444–445 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, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. Synthesis of the title compound.
	Fig. 2. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 3. Part of the crystal structure of the title compound, showing the formation of C(6) chain.
	Fig. 4. Part of the crystal structure of the title compound, showing the formation of R²₂(10) and R⁴₄(26) rings.

(3aR,6S,7aR)-7a-Chloro-6-methyl-2-(4-nitrophenylsulfonyl)-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole top

Crystal data top

C₁₅H₁₅ClN₂O₅S	F(000) = 768
M_r = 370.80	D_x = 1.512 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13941 reflections
a = 8.6049 (5) Å	θ = 1.6–27.2°
b = 7.1949 (3) Å	µ = 0.39 mm⁻¹
c = 26.8195 (15) Å	T = 296 K
β = 101.186 (4)°	Plate, colorless
V = 1628.89 (15) Å³	0.48 × 0.24 × 0.02 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	3449 independent reflections
Radiation source: fine-focus sealed tube	1564 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
rotation method scans	θ_max = 26.8°, θ_min = 1.6°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −10→10
T_min = 0.894, T_max = 0.992	k = −9→9
13941 measured reflections	l = −33→33

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.192	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.1022P)²] where P = (F_o² + 2F_c²)/3
3449 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 1.12 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₅H₁₅ClN₂O₅S	V = 1628.89 (15) Å³
M_r = 370.80	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6049 (5) Å	µ = 0.39 mm⁻¹
b = 7.1949 (3) Å	T = 296 K
c = 26.8195 (15) Å	0.48 × 0.24 × 0.02 mm
β = 101.186 (4)°

Data collection top

Stoe IPDS 2 diffractometer	3449 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1564 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.992	R_int = 0.090
13941 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.192	H-atom parameters constrained
S = 0.89	Δρ_max = 1.12 e Å⁻³
3449 reflections	Δρ_min = −0.37 e Å⁻³
217 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.5887 (5)	0.4475 (7)	0.44296 (17)	0.0556 (12)
C2	0.5543 (5)	0.2605 (7)	0.44330 (18)	0.0618 (13)
H2	0.4667	0.2139	0.4209	0.074*
C3	0.6482 (6)	0.1425 (7)	0.47633 (17)	0.0616 (13)
H3	0.6257	0.0161	0.4764	0.074*
C4	0.7759 (5)	0.2143 (7)	0.50928 (17)	0.0579 (12)
C5	0.8113 (5)	0.4015 (8)	0.51046 (17)	0.0630 (13)
H5	0.8979	0.4474	0.5334	0.076*
C6	0.7182 (5)	0.5177 (7)	0.47768 (18)	0.0608 (13)
H6	0.7405	0.6443	0.4783	0.073*
C7	0.7168 (6)	0.6656 (7)	0.34900 (18)	0.0594 (12)
H7A	0.7832	0.6501	0.3824	0.071*
H7B	0.7080	0.7971	0.3410	0.071*
C8	0.7840 (5)	0.5617 (6)	0.30954 (17)	0.0573 (12)
C9	0.9556 (6)	0.5353 (7)	0.3091 (2)	0.0727 (15)
H9	1.0398	0.5502	0.3363	0.087*
C10	0.9638 (6)	0.4871 (8)	0.2628 (2)	0.0741 (15)
H10	1.0550	0.4557	0.2510	0.089*
C11	0.7968 (6)	0.4919 (7)	0.23212 (18)	0.0599 (12)
C12	0.7102 (6)	0.3187 (7)	0.2476 (2)	0.0691 (14)
H12A	0.6075	0.3012	0.2257	0.083*
H12B	0.7730	0.2068	0.2476	0.083*
C13	0.6946 (6)	0.3746 (6)	0.30125 (18)	0.0594 (12)
C14	0.5329 (5)	0.4221 (7)	0.31263 (18)	0.0613 (12)
H14A	0.4592	0.4537	0.2816	0.074*
H14B	0.4906	0.3178	0.3286	0.074*
C15	0.7767 (7)	0.5299 (9)	0.1765 (2)	0.0832 (17)
H15A	0.8270	0.6456	0.1714	0.100*
H15B	0.6659	0.5372	0.1618	0.100*
H15C	0.8244	0.4314	0.1605	0.100*
N1	0.8795 (6)	0.0885 (8)	0.54414 (17)	0.0793 (13)
N2	0.5591 (4)	0.5831 (5)	0.34738 (13)	0.0522 (9)
O1	0.8474 (6)	−0.0760 (7)	0.54284 (18)	0.1241 (18)
O2	0.9903 (6)	0.1529 (6)	0.57330 (19)	0.1193 (17)
O3	0.4999 (4)	0.7806 (5)	0.41540 (13)	0.0780 (10)
O4	0.3234 (4)	0.5168 (6)	0.38233 (13)	0.0780 (11)
O5	0.7281 (4)	0.6367 (4)	0.25862 (11)	0.0637 (9)
S1	0.47826 (14)	0.59405 (19)	0.39663 (5)	0.0621 (4)
Cl1	0.79058 (18)	0.2099 (2)	0.34891 (6)	0.0899 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.050 (2)	0.063 (3)	0.052 (3)	−0.006 (2)	0.007 (2)	−0.009 (2)
C2	0.055 (3)	0.072 (4)	0.054 (3)	−0.019 (2)	0.002 (2)	−0.012 (2)
C3	0.072 (3)	0.059 (3)	0.053 (3)	−0.020 (2)	0.011 (2)	−0.006 (2)
C4	0.058 (3)	0.066 (3)	0.048 (3)	−0.005 (2)	0.007 (2)	0.003 (2)
C5	0.057 (3)	0.079 (4)	0.049 (3)	−0.017 (3)	0.001 (2)	−0.004 (3)
C6	0.062 (3)	0.064 (3)	0.055 (3)	−0.015 (2)	0.009 (2)	−0.009 (2)
C7	0.067 (3)	0.049 (3)	0.058 (3)	−0.011 (2)	0.001 (2)	−0.006 (2)
C8	0.054 (3)	0.052 (3)	0.061 (3)	−0.002 (2)	−0.002 (2)	−0.004 (2)
C9	0.057 (3)	0.073 (4)	0.086 (4)	−0.014 (3)	0.007 (3)	0.000 (3)
C10	0.065 (3)	0.069 (4)	0.090 (4)	−0.007 (3)	0.018 (3)	0.001 (3)
C11	0.069 (3)	0.050 (3)	0.061 (3)	0.005 (2)	0.014 (2)	−0.003 (2)
C12	0.066 (3)	0.060 (3)	0.079 (4)	−0.002 (3)	0.007 (3)	−0.018 (3)
C13	0.070 (3)	0.045 (3)	0.066 (3)	−0.004 (2)	0.018 (2)	−0.004 (2)
C14	0.058 (3)	0.056 (3)	0.066 (3)	−0.002 (2)	0.000 (2)	−0.018 (2)
C15	0.100 (4)	0.081 (4)	0.071 (4)	0.009 (3)	0.022 (3)	0.002 (3)
N1	0.085 (3)	0.083 (4)	0.064 (3)	−0.015 (3)	−0.001 (2)	0.008 (3)
N2	0.0494 (19)	0.054 (2)	0.050 (2)	−0.0019 (18)	0.0006 (16)	−0.0083 (18)
O1	0.158 (4)	0.077 (3)	0.110 (4)	−0.019 (3)	−0.042 (3)	0.016 (3)
O2	0.111 (3)	0.097 (3)	0.122 (4)	−0.026 (3)	−0.047 (3)	0.024 (3)
O3	0.084 (2)	0.073 (2)	0.073 (2)	0.0175 (19)	0.0053 (18)	−0.0221 (19)
O4	0.0455 (18)	0.107 (3)	0.078 (2)	0.0014 (18)	0.0031 (16)	−0.012 (2)
O5	0.076 (2)	0.054 (2)	0.0566 (19)	0.0075 (16)	0.0016 (16)	0.0036 (15)
S1	0.0529 (7)	0.0696 (9)	0.0603 (7)	0.0052 (6)	0.0027 (5)	−0.0132 (7)
Cl1	0.1013 (11)	0.0687 (9)	0.1046 (12)	0.0213 (8)	0.0322 (9)	0.0296 (8)

Geometric parameters (Å, º) top

C1—C2	1.378 (7)	C10—C11	1.512 (7)
C1—C6	1.401 (6)	C10—H10	0.9300
C1—S1	1.761 (5)	C11—O5	1.450 (5)
C2—C3	1.372 (7)	C11—C15	1.494 (7)
C2—H2	0.9300	C11—C12	1.549 (7)
C3—C4	1.371 (6)	C12—C13	1.524 (7)
C3—H3	0.9300	C12—H12A	0.9700
C4—C5	1.380 (7)	C12—H12B	0.9700
C4—N1	1.471 (7)	C13—C14	1.520 (6)
C5—C6	1.357 (7)	C13—Cl1	1.819 (5)
C5—H5	0.9300	C14—N2	1.476 (5)
C6—H6	0.9300	C14—H14A	0.9700
C7—N2	1.474 (6)	C14—H14B	0.9700
C7—C8	1.500 (7)	C15—H15A	0.9600
C7—H7A	0.9700	C15—H15B	0.9600
C7—H7B	0.9700	C15—H15C	0.9600
C8—O5	1.460 (5)	N1—O2	1.202 (6)
C8—C9	1.492 (7)	N1—O1	1.214 (6)
C8—C13	1.545 (6)	N2—S1	1.610 (4)
C9—C10	1.302 (7)	O3—S1	1.433 (4)
C9—H9	0.9300	O4—S1	1.426 (3)

C2—C1—C6	119.5 (4)	C15—C11—C12	116.5 (4)
C2—C1—S1	120.1 (3)	C10—C11—C12	107.0 (4)
C6—C1—S1	120.3 (4)	C13—C12—C11	100.1 (4)
C3—C2—C1	120.5 (4)	C13—C12—H12A	111.7
C3—C2—H2	119.7	C11—C12—H12A	111.7
C1—C2—H2	119.7	C13—C12—H12B	111.7
C4—C3—C2	118.8 (5)	C11—C12—H12B	111.7
C4—C3—H3	120.6	H12A—C12—H12B	109.5
C2—C3—H3	120.6	C14—C13—C12	120.0 (4)
C3—C4—C5	121.9 (5)	C14—C13—C8	103.0 (4)
C3—C4—N1	119.3 (5)	C12—C13—C8	103.5 (4)
C5—C4—N1	118.8 (4)	C14—C13—Cl1	108.3 (3)
C6—C5—C4	119.1 (4)	C12—C13—Cl1	112.4 (3)
C6—C5—H5	120.4	C8—C13—Cl1	108.7 (3)
C4—C5—H5	120.4	N2—C14—C13	105.7 (4)
C5—C6—C1	120.2 (5)	N2—C14—H14A	110.6
C5—C6—H6	119.9	C13—C14—H14A	110.6
C1—C6—H6	119.9	N2—C14—H14B	110.6
N2—C7—C8	104.9 (3)	C13—C14—H14B	110.6
N2—C7—H7A	110.8	H14A—C14—H14B	108.7
C8—C7—H7A	110.8	C11—C15—H15A	109.5
N2—C7—H7B	110.8	C11—C15—H15B	109.5
C8—C7—H7B	110.8	H15A—C15—H15B	109.5
H7A—C7—H7B	108.8	C11—C15—H15C	109.5
O5—C8—C9	100.7 (4)	H15A—C15—H15C	109.5
O5—C8—C7	111.9 (4)	H15B—C15—H15C	109.5
C9—C8—C7	126.0 (4)	O2—N1—O1	122.8 (5)
O5—C8—C13	97.0 (3)	O2—N1—C4	118.9 (5)
C9—C8—C13	110.7 (4)	O1—N1—C4	118.4 (4)
C7—C8—C13	106.6 (4)	C7—N2—C14	111.2 (3)
C10—C9—C8	106.2 (5)	C7—N2—S1	119.9 (3)
C10—C9—H9	126.9	C14—N2—S1	121.3 (3)
C8—C9—H9	126.9	C11—O5—C8	95.8 (3)
C9—C10—C11	107.0 (5)	O4—S1—O3	120.7 (2)
C9—C10—H10	126.5	O4—S1—N2	106.86 (19)
C11—C10—H10	126.5	O3—S1—N2	106.7 (2)
O5—C11—C15	112.3 (4)	O4—S1—C1	107.7 (2)
O5—C11—C10	100.6 (4)	O3—S1—C1	107.3 (2)
C15—C11—C10	117.5 (4)	N2—S1—C1	106.8 (2)
O5—C11—C12	100.6 (4)

C6—C1—C2—C3	−1.8 (7)	O5—C8—C13—Cl1	159.5 (3)
S1—C1—C2—C3	174.2 (4)	C9—C8—C13—Cl1	55.2 (5)
C1—C2—C3—C4	0.6 (7)	C7—C8—C13—Cl1	−85.1 (4)
C2—C3—C4—C5	0.7 (7)	C12—C13—C14—N2	−139.8 (4)
C2—C3—C4—N1	−178.7 (4)	C8—C13—C14—N2	−25.7 (5)
C3—C4—C5—C6	−0.8 (7)	Cl1—C13—C14—N2	89.3 (4)
N1—C4—C5—C6	178.6 (4)	C3—C4—N1—O2	−179.2 (5)
C4—C5—C6—C1	−0.4 (7)	C5—C4—N1—O2	1.4 (8)
C2—C1—C6—C5	1.7 (7)	C3—C4—N1—O1	−0.6 (8)
S1—C1—C6—C5	−174.3 (4)	C5—C4—N1—O1	180.0 (5)
N2—C7—C8—O5	83.0 (4)	C8—C7—N2—C14	5.6 (5)
N2—C7—C8—C9	−154.3 (4)	C8—C7—N2—S1	155.4 (3)
N2—C7—C8—C13	−21.9 (5)	C13—C14—N2—C7	13.2 (5)
O5—C8—C9—C10	−34.8 (5)	C13—C14—N2—S1	−136.2 (3)
C7—C8—C9—C10	−162.2 (5)	C15—C11—O5—C8	−174.7 (4)
C13—C8—C9—C10	67.1 (5)	C10—C11—O5—C8	−48.9 (4)
C8—C9—C10—C11	2.9 (6)	C12—C11—O5—C8	60.7 (4)
C9—C10—C11—O5	30.0 (5)	C9—C8—O5—C11	51.2 (4)
C9—C10—C11—C15	152.2 (5)	C7—C8—O5—C11	−172.7 (4)
C9—C10—C11—C12	−74.5 (5)	C13—C8—O5—C11	−61.6 (4)
O5—C11—C12—C13	−33.9 (4)	C7—N2—S1—O4	175.4 (3)
C15—C11—C12—C13	−155.5 (4)	C14—N2—S1—O4	−37.8 (4)
C10—C11—C12—C13	70.7 (5)	C7—N2—S1—O3	45.1 (4)
C11—C12—C13—C14	110.0 (5)	C14—N2—S1—O3	−168.1 (3)
C11—C12—C13—C8	−3.9 (5)	C7—N2—S1—C1	−69.4 (4)
C11—C12—C13—Cl1	−121.0 (4)	C14—N2—S1—C1	77.3 (4)
O5—C8—C13—C14	−85.8 (4)	C2—C1—S1—O4	28.7 (5)
C9—C8—C13—C14	169.9 (4)	C6—C1—S1—O4	−155.3 (4)
C7—C8—C13—C14	29.7 (5)	C2—C1—S1—O3	160.1 (4)
O5—C8—C13—C12	39.9 (4)	C6—C1—S1—O3	−23.9 (4)
C9—C8—C13—C12	−64.4 (5)	C2—C1—S1—N2	−85.8 (4)
C7—C8—C13—C12	155.3 (4)	C6—C1—S1—N2	90.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.93	2.46	3.205 (6)	138
C7—H7A···O2ⁱⁱ	0.97	2.51	3.219 (6)	129
C9—H9···O4ⁱⁱⁱ	0.93	2.52	3.388 (6)	155

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.93	2.46	3.205 (6)	137.7
C7—H7A···O2ⁱⁱ	0.97	2.51	3.219 (6)	129.4
C9—H9···O4ⁱⁱⁱ	0.93	2.52	3.388 (6)	154.9

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the diffractometer (purchased under grant F.279 of University Research Fund) and also The Scientific & Technological Research Council of Turkey (TÜBİTAK) for the financial support of this work (P·N.: 107 T831).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Blanc, A. & Bochet, C. G. (2007). Org. Lett. 9, 2649–2651. Web of Science CrossRef PubMed CAS Google Scholar
Büyükgüngör, O., Koşar, B., Demircan, A. & Turaç, E. (2005). Acta Cryst. E61, o1441–o1442. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chan, W. C. & White, P. D. (2004). In Fmoc Solid Phase Peptide Synthesis. Oxford University Press. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Demircan, A. & Parsons, P. J. (2002). Heterocycl. Commun. 8, 531–536. CAS Google Scholar
Demircan, A., Şahin, E., Beyazova, G., Karaaslan, M. & Hökelek, T. (2011). Acta Cryst. E67, o1085–o1086. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Demirtaş, I., Büyükkıdan, B. & Elmastaş, M. (2002). Turk. J. Chem. 26, 889–896. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Greene, T. W. & Wuts, P. G. M. (1999). Protective Groups in Organic Synthesis, 3rd ed. New York: John Wiley & Sons, Inc. Google Scholar
Karaarslan, M., Göktürk, E. & Demircan, A. (2007). J. Chem. Res. 2, 117–120. CrossRef Google Scholar
Katritzky, A. R., Hoffmann, S. & Suzuki, K. (2004). Arkivoc, xii, 14–22. CrossRef Google Scholar
Koşar, B., Demircan, A., Karaarslan, M. & Büyükgüngör, O. (2006a). Acta Cryst. E62, o765–o767. Web of Science CSD CrossRef IUCr Journals Google Scholar
Koşar, B., Göktürk, E., Demircan, A. & Büyükgüngör, O. (2006b). Acta Cryst. E62, o4192–o4193. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Merlin, P., Braekman, J. C. & Daloze, D. (1988). Tetrahedron Lett. 29, 1691–1694. CrossRef CAS Web of Science Google Scholar
Romanski, J., Nowak, P., Kosinski, K. & Jurczak, J. (2012). Tetrahedron Lett. 53, 5287–5289. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Temel, E., Demircan, A., Arslan, H. & Büyükgüngör, O. (2011). Acta Cryst. E67, o1304–o1305. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Temel, E., Demircan, A., Beyazova, G. & Büyükgüngör, O. (2012). Acta Cryst. E68, o1102–o1103. CSD CrossRef CAS IUCr Journals Google Scholar
Yasushi, K. & Higuchi, T. (2006). FEMS Microbiol. Lett. 24, 225–229. Google Scholar

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Volume 69| Part 11| November 2013| Pages o1628-o1629

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

(3aR,6S,7aR)-7a-Chloro-6-methyl-2-(4-nitro­phenyl­sulfon­yl)-1,2,3,6,7,7a-hexa­hydro-3a,6-ep­­oxy­iso­indole

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Experimental

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Refinement

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organic compounds

(3aR,6S,7aR)-7a-Chloro-6-methyl-2-(4-nitrophenylsulfonyl)-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole