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

In the title compound, C14H13ClN2O5S, the chlorine-substituted tetrahydrofuran ring adopts a twist conformation and the other tetra-hydro-furan ring an envelope conformation with the O atom as the flap. The pyrrolidine ring adopts a twist conformation. In the crystal, C-H⋯O hydrogen bonds link the mol-ecules into zigzag chains running along the b-axis direction.

Related literature

For Diels–Alder reactions, see: Winkler (1996 ▶); Paulvannan (2004 ▶); Norton (1942 ▶); Fraile et al. (2001 ▶); Padwa et al. (2003 ▶); Medimagh et al. (2008 ▶); Avalos et al. (2003 ▶). For the thermal IMDA reaction of furan-cored compounds, see: Karaarslan & Demircan (2006 ▶); Koşar et al. (2006 ▶, 2007 ▶, 2011 ▶); Arslan et al. (2008 ▶); Temel et al. (2012 ▶). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H13ClN2O5S

M = 356.77

Monoclinic,

a = 7.5193 (3) Å

b = 9.7278 (4) Å

c = 20.7616 (7) Å

β = 93.659 (3)°

V = 1515.54 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 296 K

0.68 × 0.63 × 0.60 mm

Data collection

STOE IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.811, T max = 0.850

11192 measured reflections

3151 independent reflections

2494 reflections with I > 2σ(I)

R int = 0.242

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.110

S = 1.03

3151 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.23 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, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813025336/bt6932sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025336/bt6932Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813025336/bt6932Isup3.cml

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

C14H13ClN2O5S	F(000) = 736
Mr = 356.77	Dx = 1.564 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11192 reflections
a = 7.5193 (3) Å	θ = 2.0–28.0°
b = 9.7278 (4) Å	µ = 0.42 mm−1
c = 20.7616 (7) Å	T = 296 K
β = 93.659 (3)°	Prism, colorless
V = 1515.54 (10) Å3	0.68 × 0.63 × 0.60 mm
Z = 4

STOE IPDS 2 diffractometer	3151 independent reflections
Radiation source: fine-focus sealed tube	2494 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.242
rotation method scans	θmax = 26.5°, θmin = 2.0°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −9→9
Tmin = 0.811, Tmax = 0.850	k = −12→12
11192 measured reflections	l = −26→22

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0708P)2 + 0.085P] where P = (Fo2 + 2Fc2)/3
3151 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.23 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	0.1690 (2)	0.43022 (19)	0.57226 (9)	0.0532 (4)
C2	0.2809 (3)	0.5425 (2)	0.57988 (11)	0.0647 (5)
H2	0.3807	0.5492	0.5558	0.078*
C3	0.2448 (3)	0.6445 (2)	0.62308 (11)	0.0638 (5)
H3	0.3168	0.7220	0.6277	0.077*
C4	0.0984 (2)	0.62852 (18)	0.65935 (9)	0.0530 (4)
C5	−0.0099 (3)	0.5154 (2)	0.65435 (10)	0.0627 (5)
H5	−0.1046	0.5061	0.6807	0.075*
C6	0.0234 (3)	0.4159 (2)	0.60974 (11)	0.0619 (5)
H6	−0.0507	0.3396	0.6047	0.074*
C7	0.2824 (2)	0.1007 (2)	0.60045 (9)	0.0551 (4)
H7A	0.2072	0.0270	0.5829	0.066*
H7B	0.2176	0.1526	0.6312	0.066*
C8	0.4526 (2)	0.04597 (17)	0.63097 (8)	0.0462 (4)
C9	0.4822 (3)	0.0021 (2)	0.70034 (10)	0.0629 (5)
H9	0.4132	0.0246	0.7344	0.075*
C10	0.6266 (3)	−0.0750 (2)	0.70250 (11)	0.0708 (6)
H10	0.6812	−0.1173	0.7387	0.085*
C11	0.6856 (3)	−0.0808 (2)	0.63474 (10)	0.0631 (5)
H11	0.7582	−0.1609	0.6251	0.076*
C12	0.7690 (2)	0.0595 (2)	0.61967 (10)	0.0578 (5)
H12A	0.8537	0.0891	0.6541	0.069*
H12B	0.8269	0.0576	0.5792	0.069*
C13	0.6017 (2)	0.15046 (18)	0.61523 (8)	0.0470 (4)
C14	0.5380 (2)	0.2031 (2)	0.54972 (9)	0.0566 (5)
H14A	0.5733	0.2980	0.5442	0.068*
H14B	0.5856	0.1480	0.5159	0.068*
N1	0.0537 (2)	0.73809 (18)	0.70409 (9)	0.0641 (4)
N2	0.3418 (2)	0.19055 (17)	0.54859 (7)	0.0551 (4)
O1	0.1109 (2)	0.85355 (16)	0.69498 (9)	0.0860 (5)
O2	−0.0412 (3)	0.70905 (18)	0.74790 (9)	0.0837 (5)
O3	0.0442 (2)	0.23390 (18)	0.49970 (8)	0.0769 (4)
O4	0.3033 (2)	0.36571 (18)	0.46492 (7)	0.0810 (5)
O5	0.51741 (17)	−0.07105 (13)	0.59750 (7)	0.0592 (3)
S1	0.20917 (7)	0.30168 (5)	0.51441 (2)	0.06001 (17)
Cl1	0.60735 (7)	0.28908 (5)	0.67199 (3)	0.06988 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0534 (10)	0.0544 (10)	0.0520 (9)	0.0054 (8)	0.0040 (8)	0.0121 (8)
C2	0.0608 (11)	0.0608 (11)	0.0743 (13)	−0.0031 (9)	0.0195 (10)	0.0156 (10)
C3	0.0578 (11)	0.0519 (10)	0.0817 (13)	−0.0070 (9)	0.0052 (10)	0.0105 (10)
C4	0.0515 (10)	0.0492 (9)	0.0571 (10)	0.0048 (8)	−0.0047 (8)	0.0084 (8)
C5	0.0535 (10)	0.0635 (11)	0.0726 (12)	−0.0029 (9)	0.0158 (9)	0.0020 (10)
C6	0.0525 (10)	0.0574 (10)	0.0769 (13)	−0.0088 (9)	0.0119 (9)	−0.0017 (9)
C7	0.0448 (9)	0.0584 (10)	0.0620 (11)	−0.0040 (8)	0.0040 (8)	0.0106 (8)
C8	0.0424 (8)	0.0477 (8)	0.0487 (9)	−0.0034 (7)	0.0035 (7)	0.0019 (7)
C9	0.0616 (12)	0.0735 (12)	0.0541 (10)	−0.0033 (10)	0.0082 (9)	0.0153 (9)
C10	0.0661 (13)	0.0782 (14)	0.0667 (12)	0.0053 (11)	−0.0059 (10)	0.0215 (11)
C11	0.0549 (11)	0.0626 (11)	0.0704 (12)	0.0109 (9)	−0.0069 (9)	−0.0058 (9)
C12	0.0417 (9)	0.0758 (12)	0.0559 (10)	0.0016 (9)	0.0027 (7)	−0.0089 (9)
C13	0.0434 (9)	0.0529 (9)	0.0452 (8)	−0.0062 (7)	0.0068 (7)	−0.0058 (7)
C14	0.0493 (10)	0.0691 (11)	0.0523 (10)	−0.0022 (9)	0.0104 (8)	0.0087 (8)
N1	0.0616 (10)	0.0597 (10)	0.0688 (11)	0.0112 (8)	−0.0126 (8)	−0.0010 (8)
N2	0.0484 (8)	0.0640 (9)	0.0531 (8)	0.0057 (7)	0.0055 (7)	0.0119 (7)
O1	0.0916 (12)	0.0555 (9)	0.1090 (13)	0.0002 (8)	−0.0077 (10)	−0.0062 (9)
O2	0.0914 (12)	0.0848 (11)	0.0759 (10)	0.0132 (9)	0.0141 (9)	−0.0065 (8)
O3	0.0687 (10)	0.0855 (10)	0.0735 (9)	0.0134 (8)	−0.0203 (7)	−0.0094 (8)
O4	0.1031 (13)	0.0910 (11)	0.0507 (8)	0.0235 (10)	0.0181 (8)	0.0212 (8)
O5	0.0568 (8)	0.0521 (7)	0.0672 (8)	0.0010 (6)	−0.0074 (6)	−0.0104 (6)
S1	0.0645 (3)	0.0674 (3)	0.0475 (3)	0.0122 (2)	−0.0015 (2)	0.0068 (2)
Cl1	0.0700 (3)	0.0652 (3)	0.0748 (3)	−0.0109 (2)	0.0081 (3)	−0.0243 (2)

C1—C2	1.382 (3)	C9—H9	0.9300
C1—C6	1.390 (3)	C10—C11	1.503 (3)
C1—S1	1.773 (2)	C10—H10	0.9300
C2—C3	1.376 (3)	C11—O5	1.443 (2)
C2—H2	0.9300	C11—C12	1.542 (3)
C3—C4	1.381 (3)	C11—H11	0.9800
C3—H3	0.9300	C12—C13	1.536 (3)
C4—C5	1.369 (3)	C12—H12A	0.9700
C4—N1	1.467 (3)	C12—H12B	0.9700
C5—C6	1.374 (3)	C13—C14	1.503 (3)
C5—H5	0.9300	C13—Cl1	1.7896 (17)
C6—H6	0.9300	C14—N2	1.479 (2)
C7—N2	1.478 (2)	C14—H14A	0.9700
C7—C8	1.490 (3)	C14—H14B	0.9700
C7—H7A	0.9700	N1—O1	1.222 (2)
C7—H7B	0.9700	N1—O2	1.225 (2)
C8—O5	1.435 (2)	N2—S1	1.6050 (16)
C8—C9	1.505 (3)	O3—S1	1.4208 (17)
C8—C13	1.563 (2)	O4—S1	1.4272 (15)
C9—C10	1.318 (3)
C2—C1—C6	120.70 (19)	O5—C11—C12	100.80 (15)
C2—C1—S1	120.42 (14)	C10—C11—C12	107.76 (17)
C6—C1—S1	118.88 (15)	O5—C11—H11	115.0
C3—C2—C1	120.03 (18)	C10—C11—H11	115.0
C3—C2—H2	120.0	C12—C11—H11	115.0
C1—C2—H2	120.0	C13—C12—C11	100.37 (14)
C2—C3—C4	118.14 (19)	C13—C12—H12A	111.7
C2—C3—H3	120.9	C11—C12—H12A	111.7
C4—C3—H3	120.9	C13—C12—H12B	111.7
C5—C4—C3	122.68 (18)	C11—C12—H12B	111.7
C5—C4—N1	118.22 (17)	H12A—C12—H12B	109.5
C3—C4—N1	119.08 (18)	C14—C13—C12	117.59 (14)
C4—C5—C6	118.95 (17)	C14—C13—C8	102.66 (14)
C4—C5—H5	120.5	C12—C13—C8	102.01 (14)
C6—C5—H5	120.5	C14—C13—Cl1	109.40 (13)
C5—C6—C1	119.42 (18)	C12—C13—Cl1	114.20 (13)
C5—C6—H6	120.3	C8—C13—Cl1	109.84 (11)
C1—C6—H6	120.3	N2—C14—C13	104.26 (13)
N2—C7—C8	103.29 (13)	N2—C14—H14A	110.9
N2—C7—H7A	111.1	C13—C14—H14A	110.9
C8—C7—H7A	111.1	N2—C14—H14B	110.9
N2—C7—H7B	111.1	C13—C14—H14B	110.9
C8—C7—H7B	111.1	H14A—C14—H14B	108.9
H7A—C7—H7B	109.1	O1—N1—O2	123.69 (19)
O5—C8—C7	112.73 (15)	O1—N1—C4	118.23 (19)
O5—C8—C9	101.80 (14)	O2—N1—C4	118.07 (18)
C7—C8—C9	125.36 (15)	C7—N2—C14	112.62 (14)
O5—C8—C13	98.31 (12)	C7—N2—S1	120.83 (12)
C7—C8—C13	106.67 (14)	C14—N2—S1	122.85 (13)
C9—C8—C13	108.70 (15)	C8—O5—C11	96.05 (13)
C10—C9—C8	105.36 (17)	O3—S1—O4	120.93 (11)
C10—C9—H9	127.3	O3—S1—N2	106.96 (10)
C8—C9—H9	127.3	O4—S1—N2	106.85 (9)
C9—C10—C11	106.33 (18)	O3—S1—C1	106.78 (10)
C9—C10—H10	126.8	O4—S1—C1	107.07 (10)
C11—C10—H10	126.8	N2—S1—C1	107.66 (9)
O5—C11—C10	101.43 (16)
C6—C1—C2—C3	−2.6 (3)	C7—C8—C13—Cl1	83.44 (16)
S1—C1—C2—C3	177.44 (17)	C9—C8—C13—Cl1	−54.21 (17)
C1—C2—C3—C4	2.0 (3)	C12—C13—C14—N2	139.34 (16)
C2—C3—C4—C5	0.6 (3)	C8—C13—C14—N2	28.35 (18)
C2—C3—C4—N1	−177.90 (18)	Cl1—C13—C14—N2	−88.26 (15)
C3—C4—C5—C6	−2.6 (3)	C5—C4—N1—O1	−157.46 (19)
N1—C4—C5—C6	175.92 (19)	C3—C4—N1—O1	21.1 (3)
C4—C5—C6—C1	1.9 (3)	C5—C4—N1—O2	21.4 (3)
C2—C1—C6—C5	0.6 (3)	C3—C4—N1—O2	−159.99 (19)
S1—C1—C6—C5	−179.46 (16)	C8—C7—N2—C14	−5.1 (2)
N2—C7—C8—O5	−83.60 (17)	C8—C7—N2—S1	−164.04 (13)
N2—C7—C8—C9	151.72 (18)	C13—C14—N2—C7	−15.5 (2)
N2—C7—C8—C13	23.20 (18)	C13—C14—N2—S1	142.87 (14)
O5—C8—C9—C10	32.8 (2)	C7—C8—O5—C11	173.09 (15)
C7—C8—C9—C10	162.04 (19)	C9—C8—O5—C11	−50.15 (16)
C13—C8—C9—C10	−70.3 (2)	C13—C8—O5—C11	61.04 (15)
C8—C9—C10—C11	−0.7 (2)	C10—C11—O5—C8	49.46 (17)
C9—C10—C11—O5	−31.3 (2)	C12—C11—O5—C8	−61.35 (16)
C9—C10—C11—C12	74.1 (2)	C7—N2—S1—O3	−46.28 (18)
O5—C11—C12—C13	35.15 (17)	C14—N2—S1—O3	157.01 (15)
C10—C11—C12—C13	−70.69 (18)	C7—N2—S1—O4	−177.11 (15)
C11—C12—C13—C14	−109.52 (18)	C14—N2—S1—O4	26.18 (18)
C11—C12—C13—C8	1.83 (17)	C7—N2—S1—C1	68.16 (17)
C11—C12—C13—Cl1	120.25 (14)	C14—N2—S1—C1	−88.54 (16)
O5—C8—C13—C14	83.97 (15)	C2—C1—S1—O3	−157.40 (17)
C7—C8—C13—C14	−32.86 (17)	C6—C1—S1—O3	22.68 (19)
C9—C8—C13—C14	−170.51 (15)	C2—C1—S1—O4	−26.55 (19)
O5—C8—C13—C12	−38.24 (15)	C6—C1—S1—O4	153.53 (16)
C7—C8—C13—C12	−155.07 (15)	C2—C1—S1—N2	88.03 (17)
C9—C8—C13—C12	67.28 (17)	C6—C1—S1—N2	−91.89 (17)
O5—C8—C13—Cl1	−159.73 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4i	0.93	2.58	3.437 (3)	154
C14—H14B···O5ii	0.97	2.54	3.317 (2)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O4i	0.93	2.58	3.437 (3)	154
C14—H14B⋯O5ii	0.97	2.54	3.317 (2)	137

Symmetry codes: (i) ; (ii) .