(3aR,6S,7aR)-7a-Bromo-2-[(4-methyl­phen­yl)sulfon­yl]-1,2,3,6,7,7a-hexa­hydro-3a,6-ep­oxy­isoindole

Koşar, B.; Demircan, A.; Arslan, H.; Büyükgüngör, O.

doi:10.1107/S1600536811010750

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages o994-o995

doi:10.1107/S1600536811010750

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(3aR,6S,7aR)-7a-Bromo-2-[(4-methylphenyl)sulfonyl]-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole

Başak Koşar,^a ^* Aydın Demircan,^b Hakan Arslan ^c and Orhan Büyükgüngör ^d

^aDepartment of Science Education, Faculty of Education, Sinop University, 57100-Sinop, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Nigde University, 51240-Nigde, Turkey, ^cDepartment of Chemistry, Faculty of Arts and Science, Mersin University, 33343-Mersin, Turkey, and ^dDepartment of Physics, Arts and Sciences Faculty, Ondokuz Mayıs University, 55139-Samsun, Turkey
^*Correspondence e-mail: bkosar@sinop.edu.tr

(Received 5 March 2011; accepted 22 March 2011; online 31 March 2011)

In the title compound, C₁₅H₁₆BrNO₃S, the boat form of the six-membered ring is almost symmetrical with respect to the epoxy bridge. The two five-membered rings generated by the epoxy bridge of the six-membered ring adopt envelope conformations, whereas the N-containing five-membered ring adopts a twisted conformation. In the crystal, molecules are linked by C—H⋯O hydrogen bonds.

Related literature

For general background to intramolecular Diels–Alder reactions and heteroaromatic Diels–Alder reactions, see: Dell (1998 ); Kappe et al. (1997 ); Arai et al. (2010 ); Lohse & Hsung (2009 ). For related structures, see: Koşar et al. (2006 , 2007a ,b ). For the synthesis of the title compound and related compounds, see: Carlini et al. (1997 ); Hart et al. (1997 ); Shing et al. (1996 ); Karaarslan et al. (2007 ); Pontén & Magnusson (1997 ); Demircan et al. (2006 ); Arslan & Demircan (2008 ); Demircan & Parsons (1998 ). For puckering analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₅H₁₆BrNO₃S
M_r = 370.26
Monoclinic, P 2₁ /c
a = 16.5136 (6) Å
b = 6.2186 (3) Å
c = 16.3487 (7) Å
β = 113.802 (3)°
V = 1536.07 (12) Å³
Z = 4
Mo Kα radiation
μ = 2.82 mm⁻¹
T = 296 K
0.58 × 0.44 × 0.31 mm

Data collection

STOE IPDS 2 CCD diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.310, T_max = 0.495
7305 measured reflections
3163 independent reflections
2353 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.126
S = 1.07
3163 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O1ⁱ	0.97	2.50	3.382 (6)	151
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), OLEX2, publCIF (Westrip, 2010 ) and Mercury (Macrae et al., 2006 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010750/zl2354sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010750/zl2354Isup2.hkl

checkCIF report

Comment top

Thermal intramolecular [4 + 2] type cycloaddition processes, or intramolecular Diels Alder (IMDA) reactions, have been a highly useful tool for the construction of many cycloaddition products (Dell, 1998). The IMDA reaction is especially useful for asymmetrical syntheses towards natural products such as, (±)-xestoquinone (Carlini et al., 1997), (+)-himbelive (Hart et al., 1997) and (S)-(±)-carvone (Shing et al., 1996). In this context, the use of heteroaromatic compounds has been gaining popularity (Kappe et al., 1997). IMDA reactions with furan derivatives, called IMDAF, have been widely used for the construction of some new molecules (Karaarslan et al., 2007; Pontén & Magnusson, 1997; Demircan et al., 2006; Koşar et al., 2007a; Koşar et al., 2007b; Arslan & Demircan, 2008; Demircan & Parsons, 1998; Koşar et al., 2006). These compounds have been used as strategic intermediates in combinatorial synthesis.

In view of a recent literature research (Arai et al., 2010; Lohse & Hsung, 2009), we would like to report here a thermal IMDAF reaction of an alkenyl furan with a nitrogen linked chain which undergoes intramolecular cycloaddition upon heating to 371 K for two days (Fig. 1 and 2). The product of the intramolecular thermal cycloaddition reaction of compound (I) was characterized by ¹H NMR, ¹³C NMR, FT-IR, MS, elemental analysis and X-ray single crystal diffraction studies. Despite of the presence of three new stereocenters in the product molecules only one pair of mirror symmetric enatiomers was formed in the reaction, i.e. the intramolecular thermal cycloaddition of II to I is diastereoselective under the chosen reaction conditions.

Related with the above mentioned reaction, we presented here the crystal structure of the title compound, C₁₅H₁₆BrNO₃S. Fig. 1 shows the molecular structure of the title compound, I. The pyrrolidine (C4/C5/N1/C6/C7) ring adopts a twisted conformation with a total puckering parameter Q_T value of 0.329 (5) Å (Cremer & Pople, 1975). The tetrahydrofuran (O1/C1-C4) and bromo-attached tetrahydrofuran (O1/C4/C7/C8/C1) rings adopt envelope conformations with total puckering parameters of 0.514 (5) and 0.627 (5) Å, respectively.

The title compound displays an intramolecular hydrogen bond between atoms C10 and O2 and the crystal structure is stabilized by weak van der Waals interactions and a weak intermolecular hydrogen bond, C6—H6a···O1 in a three dimensional network (Fig. 3). Geometrical parameters of the intra- and intermolecular H-bonds are listed in Table 1.

Related literature top

For general background to intramolecular Diels–Alder reactions and heteroaromatic Diels–Alder reactions, see: Dell (1998); Kappe et al. (1997); Arai et al. (2010); Lohse & Hsung (2009). For related structures, see: Koşar et al. (2006, 2007a,b). For the synthesis of the title compound and related compounds, see: Carlini et al. (1997); Hart et al. (1997); Shing et al. (1996); Karaarslan et al. (2007); Pontén & Magnusson (1997); Demircan et al. (2006); Arslan & Demircan (2008); Demircan & Parsons (1998). For puckering analysis, see: Cremer & Pople (1975).

Experimental top

N-(2-Bromoprop-2-en-1-yl)-4-methyl-N-[(5-methyl-2-furyl)methyl]benzenesulfonamide, II, (1 g, 2.7 mmol) was stirred and heated under reflux in water (25 mL) at 372 K for two days (Fig. 2). The mixture was poured into ethyl acetate (25 mL) and the aqueous phase was washed with excess ethyl acetate (2 x 25 mL). The combined organic phases were dried over magnesium sulphate and filtered off. The solvent was then removed under reduced pressure. The residue was subjected to flash column chromatography (R_f(Hexane:Ethyl acetate = 7:3): 0.47) to afford I (0.7 g, 70 % yield) as yellow crystals. M. p.: 396-398 K, ν_max(Thin film) / cm^-1: 2932 (s, CH), 2161 (m, SO), 1977 (m, S=O), 1453, 1159, 1065 (s, C-O). δ_H (400 MHz, CDCl₃): 7,67 (d, 2H, J = 8 Hz), 7.24 (d, 2H, J = 8 Hz, H10-H13), 6.40 (dd, 1H, J = 5.6 Hz, J = 1.8 Hz, AB), 6.34 (d, 1H, J = 5.6 Hz, AB), 4.95 (dd, 1H, J = 4.5 Hz, J = 1.8 Hz), 4.06 (d, 1H, J = 12 Hz), 4.01 (d, 1H, J = 12 Hz), 3.67 (d, 1H, J = 12 Hz), 3.43 (d, 1H, J = 12 Hz), 2.39 (dd, 1H, J = 4.5 Hz, J = 12 Hz), 2.36 (s, 3H), 1.63 (d, 1H, J = 12 Hz). δ_C (100 MHz, CDCl₃): 143.8, 137.2, 134.7, 134.5, 129.9 (2 x C), 127.7 (2 x C), 97.2, 81.0, 64.0, 63.3, 47.5, 41.4, 21.7. m/z (70 eV, EI): 371,00 [M⁺(⁸¹Br), 42%)], 369, [M⁺(⁷⁹Br, 42%)], 216,00 [M⁺(⁸¹Br)-Ts, 100%], 214 [M⁺(⁷⁹Br)-H+Ts, 100%]. Elemental Analysis (C₁₅H₁₆BrNO₃S): % Calculated (Found): C, 48.66 (48.72); H, 4.36 (4.39); N, 3.78 (3.74).

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: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010) and Mercury (Macrae et al., 2006).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Synthesis of the title compound.
	Fig. 3. A packing diagram of the title compound. Dashed lines indicate the O—H···O intermolecular hydrogen bonds.

(3aR,6S,7aR)-7a-Bromo-2-[(4-methylphenyl)sulfonyl]- 1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole top

Crystal data top

C₁₅H₁₆BrNO₃S	F(000) = 752
M_r = 370.26	D_x = 1.601 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 10108 reflections
a = 16.5136 (6) Å	θ = 1.5–28.0°
b = 6.2186 (3) Å	µ = 2.82 mm⁻¹
c = 16.3487 (7) Å	T = 296 K
β = 113.802 (3)°	Prism, colourless
V = 1536.07 (12) Å³	0.58 × 0.44 × 0.31 mm
Z = 4

Data collection top

STOE IPDS 2 CCD diffractometer	3163 independent reflections
Radiation source: fine-focus sealed tube	2353 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.042
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 2.5°
rotation method scans	h = −20→20
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −7→7
T_min = 0.310, T_max = 0.495	l = −20→20
7305 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0617P)² + 0.5082P] where P = (F_o² + 2F_c²)/3
3163 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₅H₁₆BrNO₃S	V = 1536.07 (12) Å³
M_r = 370.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.5136 (6) Å	µ = 2.82 mm⁻¹
b = 6.2186 (3) Å	T = 296 K
c = 16.3487 (7) Å	0.58 × 0.44 × 0.31 mm
β = 113.802 (3)°

Data collection top

STOE IPDS 2 CCD diffractometer	3163 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2353 reflections with I > 2σ(I)
T_min = 0.310, T_max = 0.495	R_int = 0.042
7305 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.07	Δρ_max = 0.40 e Å⁻³
3163 reflections	Δρ_min = −0.44 e Å⁻³
190 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
C1	0.9623 (3)	0.6757 (7)	0.0923 (3)	0.0640 (11)
H1	1.0211	0.7174	0.0966	0.077*
C2	0.9042 (3)	0.5742 (8)	0.0062 (3)	0.0681 (12)
H2	0.9082	0.5913	−0.0485	0.082*
C3	0.8459 (3)	0.4559 (7)	0.0218 (3)	0.0617 (10)
H3	0.8013	0.3717	−0.0189	0.074*
C4	0.8668 (3)	0.4857 (6)	0.1192 (3)	0.0537 (9)
C5	0.8358 (3)	0.3394 (6)	0.1725 (3)	0.0642 (11)
H5A	0.7765	0.2875	0.1372	0.077*
H5B	0.8753	0.2172	0.1945	0.077*
C6	0.8569 (3)	0.7032 (6)	0.2354 (3)	0.0519 (9)
H6A	0.9170	0.7400	0.2752	0.062*
H6B	0.8163	0.7984	0.2472	0.062*
C7	0.8443 (3)	0.7184 (6)	0.1376 (3)	0.0489 (8)
C8	0.9107 (3)	0.8549 (7)	0.1161 (3)	0.0571 (10)
H8A	0.9488	0.9380	0.1674	0.069*
H8B	0.8812	0.9506	0.0660	0.069*
C9	0.6718 (3)	0.5012 (6)	0.2434 (3)	0.0526 (9)
C10	0.6473 (3)	0.7028 (7)	0.2619 (3)	0.0617 (10)
H10	0.6869	0.7852	0.3082	0.074*
C11	0.5636 (4)	0.7800 (8)	0.2109 (4)	0.0736 (13)
H11	0.5473	0.9149	0.2236	0.088*
C12	0.5033 (3)	0.6607 (9)	0.1410 (3)	0.0724 (12)
C13	0.5291 (3)	0.4605 (9)	0.1249 (3)	0.0725 (12)
H13	0.4891	0.3777	0.0790	0.087*
C14	0.6117 (3)	0.3787 (7)	0.1743 (3)	0.0627 (11)
H14	0.6273	0.2429	0.1617	0.075*
C15	0.4125 (5)	0.7472 (12)	0.0862 (5)	0.117 (2)
H15A	0.3802	0.6448	0.0408	0.175*
H15B	0.4175	0.8799	0.0586	0.175*
H15C	0.3818	0.7722	0.1242	0.175*
N1	0.8373 (2)	0.4748 (5)	0.2466 (2)	0.0526 (8)
O1	0.96199 (18)	0.5098 (4)	0.15645 (19)	0.0589 (7)
O2	0.8163 (2)	0.5198 (5)	0.38595 (19)	0.0729 (8)
O3	0.7776 (2)	0.1766 (5)	0.3018 (2)	0.0707 (8)
S1	0.78021 (8)	0.40698 (16)	0.30290 (6)	0.0559 (3)
Br1	0.71982 (3)	0.78750 (8)	0.06223 (3)	0.06777 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.060 (3)	0.068 (3)	0.066 (3)	0.007 (2)	0.028 (2)	0.000 (2)
C2	0.082 (3)	0.067 (3)	0.057 (2)	0.019 (2)	0.030 (2)	−0.001 (2)
C3	0.072 (3)	0.057 (2)	0.055 (2)	0.006 (2)	0.024 (2)	−0.0128 (19)
C4	0.058 (2)	0.043 (2)	0.054 (2)	0.0055 (17)	0.0174 (19)	−0.0063 (17)
C5	0.088 (3)	0.041 (2)	0.069 (3)	−0.003 (2)	0.038 (3)	−0.0124 (19)
C6	0.062 (2)	0.0406 (19)	0.053 (2)	−0.0077 (17)	0.0232 (19)	−0.0103 (17)
C7	0.050 (2)	0.0403 (18)	0.052 (2)	0.0033 (16)	0.0160 (17)	−0.0051 (16)
C8	0.064 (3)	0.047 (2)	0.061 (2)	0.0017 (18)	0.026 (2)	−0.0006 (18)
C9	0.064 (2)	0.044 (2)	0.054 (2)	−0.0029 (18)	0.029 (2)	0.0008 (17)
C10	0.069 (3)	0.052 (2)	0.067 (3)	−0.002 (2)	0.031 (2)	−0.008 (2)
C11	0.084 (3)	0.059 (3)	0.090 (3)	0.013 (2)	0.048 (3)	0.003 (2)
C12	0.063 (3)	0.083 (3)	0.073 (3)	0.007 (2)	0.030 (2)	0.004 (3)
C13	0.066 (3)	0.078 (3)	0.069 (3)	−0.011 (2)	0.022 (2)	−0.009 (2)
C14	0.068 (3)	0.052 (2)	0.069 (3)	−0.006 (2)	0.029 (2)	−0.008 (2)
C15	0.087 (4)	0.140 (6)	0.113 (5)	0.038 (4)	0.029 (4)	0.004 (4)
N1	0.065 (2)	0.0388 (16)	0.0541 (18)	0.0059 (14)	0.0239 (16)	−0.0009 (13)
O1	0.0538 (16)	0.0582 (17)	0.0582 (16)	0.0158 (13)	0.0159 (13)	0.0002 (13)
O2	0.092 (2)	0.077 (2)	0.0429 (14)	−0.0032 (18)	0.0201 (15)	−0.0060 (14)
O3	0.089 (2)	0.0489 (17)	0.0693 (19)	0.0038 (15)	0.0267 (18)	0.0154 (14)
S1	0.0708 (7)	0.0462 (5)	0.0474 (5)	0.0020 (4)	0.0203 (5)	0.0036 (4)
Br1	0.0521 (2)	0.0697 (3)	0.0701 (3)	0.0172 (2)	0.01277 (19)	0.0041 (2)

Geometric parameters (Å, º) top

C1—O1	1.472 (5)	C8—H8A	0.9700
C1—C2	1.487 (7)	C8—H8B	0.9700
C1—C8	1.544 (6)	C9—C10	1.388 (6)
C1—H1	0.9800	C9—C14	1.392 (6)
C2—C3	1.316 (7)	C9—S1	1.757 (4)
C2—H2	0.9300	C10—C11	1.380 (7)
C3—C4	1.498 (5)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.390 (8)
C4—O1	1.446 (5)	C11—H11	0.9300
C4—C5	1.487 (6)	C12—C13	1.375 (7)
C4—C7	1.553 (5)	C12—C15	1.502 (8)
C5—N1	1.467 (5)	C13—C14	1.373 (7)
C5—H5A	0.9700	C13—H13	0.9300
C5—H5B	0.9700	C14—H14	0.9300
C6—N1	1.484 (5)	C15—H15A	0.9600
C6—C7	1.530 (5)	C15—H15B	0.9600
C6—H6A	0.9700	C15—H15C	0.9600
C6—H6B	0.9700	N1—S1	1.616 (3)
C7—C8	1.535 (6)	O2—S1	1.427 (3)
C7—Br1	1.971 (4)	O3—S1	1.433 (3)

O1—C1—C2	101.0 (4)	C1—C8—H8A	111.7
O1—C1—C8	99.5 (3)	C7—C8—H8B	111.7
C2—C1—C8	109.5 (4)	C1—C8—H8B	111.7
O1—C1—H1	115.0	H8A—C8—H8B	109.5
C2—C1—H1	115.0	C10—C9—C14	119.7 (4)
C8—C1—H1	115.0	C10—C9—S1	120.1 (3)
C3—C2—C1	107.2 (4)	C14—C9—S1	120.1 (3)
C3—C2—H2	126.4	C11—C10—C9	119.5 (4)
C1—C2—H2	126.4	C11—C10—H10	120.3
C2—C3—C4	105.3 (4)	C9—C10—H10	120.3
C2—C3—H3	127.3	C10—C11—C12	121.4 (4)
C4—C3—H3	127.3	C10—C11—H11	119.3
O1—C4—C5	112.9 (3)	C12—C11—H11	119.3
O1—C4—C3	101.9 (3)	C13—C12—C11	117.8 (5)
C5—C4—C3	124.1 (4)	C13—C12—C15	121.5 (5)
O1—C4—C7	97.3 (3)	C11—C12—C15	120.7 (5)
C5—C4—C7	106.9 (3)	C14—C13—C12	122.3 (5)
C3—C4—C7	110.5 (3)	C14—C13—H13	118.8
N1—C5—C4	103.8 (3)	C12—C13—H13	118.8
N1—C5—H5A	111.0	C13—C14—C9	119.3 (4)
C4—C5—H5A	111.0	C13—C14—H14	120.4
N1—C5—H5B	111.0	C9—C14—H14	120.4
C4—C5—H5B	111.0	C12—C15—H15A	109.5
H5A—C5—H5B	109.0	C12—C15—H15B	109.5
N1—C6—C7	104.1 (3)	H15A—C15—H15B	109.5
N1—C6—H6A	110.9	C12—C15—H15C	109.5
C7—C6—H6A	110.9	H15A—C15—H15C	109.5
N1—C6—H6B	110.9	H15B—C15—H15C	109.5
C7—C6—H6B	110.9	C5—N1—C6	112.2 (3)
H6A—C6—H6B	108.9	C5—N1—S1	120.1 (3)
C6—C7—C8	117.7 (3)	C6—N1—S1	121.8 (2)
C6—C7—C4	101.7 (3)	C4—O1—C1	95.1 (3)
C8—C7—C4	102.9 (3)	O2—S1—O3	120.16 (19)
C6—C7—Br1	109.5 (3)	O2—S1—N1	107.28 (19)
C8—C7—Br1	113.4 (3)	O3—S1—N1	105.97 (18)
C4—C7—Br1	110.7 (3)	O2—S1—C9	107.7 (2)
C7—C8—C1	100.1 (3)	O3—S1—C9	107.9 (2)
C7—C8—H8A	111.7	N1—S1—C9	107.18 (17)

O1—C1—C2—C3	31.5 (4)	C10—C11—C12—C13	1.0 (7)
C8—C1—C2—C3	−72.9 (5)	C10—C11—C12—C15	−180.0 (5)
C1—C2—C3—C4	0.8 (5)	C11—C12—C13—C14	−1.0 (7)
C2—C3—C4—O1	−33.6 (4)	C15—C12—C13—C14	−180.0 (5)
C2—C3—C4—C5	−162.1 (4)	C12—C13—C14—C9	0.2 (7)
C2—C3—C4—C7	68.9 (4)	C10—C9—C14—C13	0.6 (6)
O1—C4—C5—N1	80.2 (4)	S1—C9—C14—C13	−176.0 (3)
C3—C4—C5—N1	−156.0 (4)	C4—C5—N1—C6	7.1 (5)
C7—C4—C5—N1	−25.6 (4)	C4—C5—N1—S1	160.4 (3)
N1—C6—C7—C8	−139.8 (3)	C7—C6—N1—C5	14.3 (5)
N1—C6—C7—C4	−28.3 (4)	C7—C6—N1—S1	−138.6 (3)
N1—C6—C7—Br1	88.8 (3)	C5—C4—O1—C1	−174.3 (3)
O1—C4—C7—C6	−82.6 (3)	C3—C4—O1—C1	50.3 (3)
C5—C4—C7—C6	34.1 (4)	C7—C4—O1—C1	−62.5 (3)
C3—C4—C7—C6	171.8 (3)	C2—C1—O1—C4	−49.4 (3)
O1—C4—C7—C8	39.7 (4)	C8—C1—O1—C4	62.7 (3)
C5—C4—C7—C8	156.4 (4)	C5—N1—S1—O2	160.6 (3)
C3—C4—C7—C8	−65.9 (4)	C6—N1—S1—O2	−48.6 (4)
O1—C4—C7—Br1	161.2 (2)	C5—N1—S1—O3	31.1 (4)
C5—C4—C7—Br1	−82.2 (4)	C6—N1—S1—O3	−178.1 (3)
C3—C4—C7—Br1	55.6 (4)	C5—N1—S1—C9	−83.9 (3)
C6—C7—C8—C1	108.8 (4)	C6—N1—S1—C9	66.9 (3)
C4—C7—C8—C1	−2.0 (4)	C10—C9—S1—O2	23.2 (4)
Br1—C7—C8—C1	−121.5 (3)	C14—C9—S1—O2	−160.2 (3)
O1—C1—C8—C7	−35.8 (4)	C10—C9—S1—O3	154.3 (3)
C2—C1—C8—C7	69.5 (4)	C14—C9—S1—O3	−29.1 (4)
C14—C9—C10—C11	−0.6 (6)	C10—C9—S1—N1	−92.0 (3)
S1—C9—C10—C11	176.1 (3)	C14—C9—S1—N1	84.6 (3)
C9—C10—C11—C12	−0.3 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1ⁱ	0.97	2.50	3.382 (6)	151
C10—H10···O2	0.93	2.59	2.937 (6)	103

Symmetry code: (i) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆BrNO₃S
M_r	370.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.5136 (6), 6.2186 (3), 16.3487 (7)
β (°)	113.802 (3)
V (Å³)	1536.07 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.82
Crystal size (mm)	0.58 × 0.44 × 0.31

Data collection
Diffractometer	STOE IPDS 2 CCD diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.310, 0.495
No. of measured, independent and observed [I > 2σ(I)] reflections	7305, 3163, 2353
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.126, 1.07
No. of reflections	3163
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.44

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1ⁱ	0.97	2.50	3.382 (6)	151
C10—H10···O2	0.93	2.59	2.937 (6)	103

Symmetry code: (i) −x+2, y+1/2, −z+1/2.

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 financial support of this work (PN: 107 T831).

References

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Volume 67| Part 4| April 2011| Pages o994-o995

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

(3aR,6S,7aR)-7a-Bromo-2-[(4-methyl­phen­yl)sulfon­yl]-1,2,3,6,7,7a-hexa­hydro-3a,6-ep­­oxy­iso­indole

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3aR,6S,7aR)-7a-Bromo-2-[(4-methylphenyl)sulfonyl]-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole