(3aR,6S,7aR)-7a-Chloro-6-methyl-2-(4-nitro-phenyl-sulfon-yl)-1,2,3,6,7,7a-hexa-hydro-3a,6-ep-oxy-iso-indole.

In the title compound, C15H15ClN2O5S, the tetra-hydro-furan 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 R (2) 2(20) and R (4) 4(26) rings, with adjacent rings running parallel to ac plane. Further C-H⋯O hydrogen bonds form a C(6) chain, linking the mol-ecules in the b-axis direction.

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 = 370.80

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.192

S = 0.89

3449 reflections

217 parameters

H-atom parameters constrained

Δρmax = 1.12 e Å−3

Δρmin = −0.37 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813026329/bt6935sup1.cif

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813026329/bt6935Isup3.cml

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

C15H15ClN2O5S	F(000) = 768
Mr = 370.80	Dx = 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

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

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(Fo2) + (0.1022P)2] where P = (Fo2 + 2Fc2)/3
3449 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 1.12 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) ; (iii) .