(rac-5RS,7RS,8SR)-Spiro­[7-methoxy­carbonyl-1-aza-3-thia­bi­cyclo­[3.3.0]­octane-8,1′-ace­naphthyl­en]-2′-one

Sundar, T.V.; Parthasarathi, V.; Álvarez-Rúa, C.; García-Granda, S.; Saxena, A.; Pardasani, P.; Pardasani, R.T.

doi:10.1107/S1600536802020846

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(rac-5RS,7RS,8SR)-Spiro[7-methoxycarbonyl-1-aza-3-thiabicyclo[3.3.0]octane-8,1'-acenaphthylen]-2'-one

T. V. Sundar, V. Parthasarathi, C. Álvarez-Rúa, S. García-Granda, A. Saxena, P. Pardasani and R. T. Pardasani

The title compound, C₁₉H₁₇NO₃S, crystallizes in the monoclinic space group P2₁/c, with four molecules in the unit cell. The structure contains a spiro-carbon connecting a bicyclo-octane group, consisting of two fused five-membered rings, to an acenaphthylene moiety. The five-membered ring containing the S atom is in an envelope conformation. The conformation of the other five-membered ring of the bicyclo-octane moiety is close to a half-chair. The methoxycarbonyl group is equatorially substituted.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802020846/na6181sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802020846/na6181Isup2.hkl Contains datablock I

CCDC reference: 202342

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.038
wR factor = 0.104
Data-to-parameter ratio = 13.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



CELLV_02  Alert A The supplied cell volume s.u. differs from that
          calculated from the cell parameter s.u.'s by > 8
          Calculated cell volume su =      11.65
          Cell volume su given      =       3.00


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 0 Alert Level C = Please check

Comment top

We are interested in the X-ray structure determination of some novel polycyclic spiro-heterocyclic compounds as they can be used as precursors for the total synthesis of naturally occurring alkaloids (Grundon, 1988). The bicyclo-octane ring has three chiral atoms, viz. C5, C7 and C8, and the present coordinates of the atoms correspond to 5R, 7R and 8S. However, the compound crystallizes as a racemic mixture in the space group P2₁/c. The angles around spiro atom C8 are C7—C8—N1 = 103.34 (12)°, C9—C8—C18 = 102.40 (12)°, N1—C8—C18 = 116.20 (13)° and C7—C8—C9 = 111.24 (13)°. The methoxycarbonyl group is equatorially substituted at C7. The acenaphthylene moiety is bisectionally substituted at C8.

The Csp²═Csp² distances in the acenaphthylene group range from 1.366 (3) (C15—C16) to 1.570 (2) Å (C8—C9) and the C—C—C bond angles range from 102.40 (12) (C9—C8—C18) to 133.02 (14)° (C8—C18—C17). These values compare well with those of previously reported related structures (Hazell, 1976; Hazell & Hazell, 1977; Hazell & Weigelt, 1976; Jones et al., 1992).

Both the fused five-membered rings of the bicyclo-octane moiety are puckered. The N1/C2/S3/C4/C5 five-membered ring of the bicyclo-octane group is in envelope conformation [puckering parameters Q = 0.498 (2) Å and ϕ = 176.2 (2)° for the atom sequence S3—C2—N1—C5—C4; Cremer & Pople, 1975], with atom S3 in the flap position. The torsion angle C2—S3—C4—C5 is −39.58 (12)°, while the angle C4—S3—C2—N1 is 38.80 (12)°. The conformation of the other five-membered ring (N1/C5/C6/C7/C8) of the bicyclo-octane group is close to a half-chair [puckering parameters Q = 0.384 (2) Å and ϕ = 86.4 (3)° for the atom sequence N1—C5—C6—C7—C8]. The dihedral angle between the least-squares planes of the above two rings is 51.96 (10)°.

The C5—N1 bond distance is 1.488 (2) Å. This is comparable to the Csp³—Nsp³ distances found in similar structures (Sussman & Wodak, 1973; Wodak, 1975). The geometry around the N atom is pyramidal. The bond distance C2—S3 is 1.8323 (18) Å and S3—C4 is 1.8044 (18) Å. The angle C2—S3—C4 is 86.99 (8)°. The structure is stabilized mainly by van der Waals interactions.

Experimental top

A mixture of acenaphthylene-1,2-dione (0.364 g, 2 mmol), (R)-(-)-thiazolidine-4-carboxylic acid (0.27 g, 2 mmol) and methyl acrylate (0.172 g, 2 mmol), in an equimolar ratio, was refluxed for 22 h in acetonitrile under a nitrogen atmosphere. After completion of the reaction, monitored by the disappearance of the acenaphthylene-1,2-dione spot in TLC analysis, the reaction mixture was filtered to remove the unreacted acid. The filtrate was concentrated in vaccuo and kept at 273 K. A yellow crystalline solid was obtained and recrystallized from chloroform/n-hexane as yellow cuboidal crystals (0.604 g, 75%; m.p. 445 K). A small amount of the compound (0.2 g; code: sp1) was dissolved in chloroform (2 ml). N-Hexane (8 ml) was layered carefully down the side of the test tube on to the solution. The volume ratio of solvent-to-precipitant was 1:4. The test tube was corked with cotton wool and left to stand undisturbed for 24 h. As the precipitant (n-hexane) diffused into the solution, crystals were formed at the interface.

Computing details top

Data collection: COLLECT (Nonius, 1997-2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Version 1.64.02; Farrugia, 1999) and PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

[rac-5RS,7RS,8SR]-Spiro-{7-methoxycarbonyl-1-aza-3-thia-bicyclo[3.3.0] octane-8,1'-acenaphthylene}-2'-one top

Crystal data top

C₁₉H₁₇NO₃S	F(000) = 712
M_r = 339.40	D_x = 1.398 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 445 K K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54180 Å
a = 9.3597 (1) Å	Cell parameters from 9012 reflections
b = 14.7896 (2) Å	θ = 2.2–68.3°
c = 14.9199 (1) Å	µ = 1.93 mm⁻¹
β = 128.660 (5)°	T = 293 K
V = 1612.73 (3) Å³	Cuboidal, yellow
Z = 4	0.32 × 0.20 × 0.18 mm

Data collection top

Nonius KappaCCD diffractometer	2926 independent reflections
Radiation source: fine-focus sealed tube	2567 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromator	R_int = 0.051
Detector resolution: 9 pixels mm^-1	θ_max = 68.2°, θ_min = 4.8°
CCD scans	h = −11→11
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −17→17
T_min = 0.583, T_max = 0.707	l = −16→17
21038 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0531P)² + 0.4649P] where P = (F_o² + 2F_c²)/3
2926 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₉H₁₇NO₃S	V = 1612.73 (3) Å³
M_r = 339.40	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 9.3597 (1) Å	µ = 1.93 mm⁻¹
b = 14.7896 (2) Å	T = 293 K
c = 14.9199 (1) Å	0.32 × 0.20 × 0.18 mm
β = 128.660 (5)°

Data collection top

Nonius KappaCCD diffractometer	2926 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	2567 reflections with I > 2σ(I)
T_min = 0.583, T_max = 0.707	R_int = 0.051
21038 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.04	Δρ_max = 0.19 e Å⁻³
2926 reflections	Δρ_min = −0.34 e Å⁻³
218 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
S3	0.26303 (6)	0.08386 (3)	0.06725 (4)	0.05249 (16)
O22	0.74525 (19)	0.27439 (9)	0.46087 (13)	0.0619 (4)
O23	0.58168 (17)	0.27574 (9)	0.52329 (11)	0.0546 (3)
O24	0.27064 (19)	0.08378 (9)	0.44632 (12)	0.0574 (4)
N1	0.28855 (18)	0.07423 (9)	0.25458 (11)	0.0401 (3)
C2	0.1478 (2)	0.08038 (12)	0.13113 (15)	0.0475 (4)
H2A	0.0753	0.1346	0.1114	0.057*
H2B	0.0672	0.0284	0.1028	0.057*
C4	0.4218 (3)	0.00210 (12)	0.17430 (15)	0.0484 (4)
H4A	0.3696	−0.0582	0.1517	0.058*
H4B	0.5348	0.0023	0.1845	0.058*
C5	0.4570 (2)	0.03062 (11)	0.28494 (14)	0.0426 (4)
H5	0.4866	−0.0228	0.3327	0.051*
C6	0.6051 (2)	0.10149 (12)	0.35478 (15)	0.0456 (4)
H6A	0.7246	0.0737	0.4082	0.055*
H6B	0.6078	0.1429	0.3055	0.055*
C7	0.5478 (2)	0.14936 (11)	0.41771 (14)	0.0409 (4)
H7	0.5771	0.1100	0.4800	0.049*
C8	0.3359 (2)	0.15526 (10)	0.32627 (14)	0.0381 (4)
C9	0.2410 (2)	0.14539 (11)	0.38304 (14)	0.0419 (4)
C10	0.1118 (2)	0.22119 (11)	0.34306 (14)	0.0414 (4)
C11	−0.0125 (2)	0.24317 (13)	0.36030 (16)	0.0506 (4)
H11	−0.0269	0.2069	0.4051	0.061*
C12	−0.1166 (3)	0.32196 (14)	0.30814 (17)	0.0576 (5)
H12	−0.2021	0.3371	0.3183	0.069*
C13	−0.0974 (3)	0.37766 (13)	0.24282 (16)	0.0545 (5)
H13	−0.1687	0.4296	0.2105	0.065*
C14	0.0299 (2)	0.35699 (11)	0.22402 (14)	0.0446 (4)
C15	0.0636 (3)	0.40655 (11)	0.15746 (15)	0.0491 (4)
H15	0.0020	0.4605	0.1228	0.059*
C16	0.1868 (2)	0.37492 (12)	0.14433 (15)	0.0483 (4)
H16	0.2057	0.4079	0.0995	0.058*
C17	0.2870 (2)	0.29369 (11)	0.19641 (14)	0.0436 (4)
H17	0.3699	0.2740	0.1858	0.052*
C18	0.2595 (2)	0.24480 (10)	0.26252 (13)	0.0376 (3)
C19	0.1313 (2)	0.27712 (10)	0.27512 (13)	0.0383 (3)
C20	0.6378 (2)	0.23927 (12)	0.46830 (14)	0.0429 (4)
C21	0.6547 (3)	0.36344 (14)	0.5738 (2)	0.0668 (6)
H21A	0.7791	0.3673	0.6024	0.100*
H21B	0.6505	0.3721	0.6360	0.100*
H21C	0.5830	0.4094	0.5169	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S3	0.0547 (3)	0.0557 (3)	0.0444 (3)	0.0032 (2)	0.0297 (2)	0.00345 (19)
O22	0.0651 (8)	0.0608 (8)	0.0780 (9)	−0.0171 (7)	0.0536 (8)	−0.0156 (7)
O23	0.0581 (8)	0.0573 (8)	0.0582 (8)	−0.0050 (6)	0.0411 (7)	−0.0122 (6)
O24	0.0713 (9)	0.0543 (8)	0.0657 (8)	0.0088 (6)	0.0521 (8)	0.0171 (6)
N1	0.0376 (7)	0.0389 (7)	0.0435 (7)	−0.0004 (5)	0.0253 (6)	−0.0014 (6)
C2	0.0390 (9)	0.0483 (10)	0.0469 (10)	−0.0027 (7)	0.0228 (8)	−0.0053 (7)
C4	0.0530 (10)	0.0428 (9)	0.0540 (10)	0.0014 (7)	0.0357 (9)	−0.0009 (8)
C5	0.0432 (9)	0.0383 (8)	0.0466 (9)	0.0052 (7)	0.0282 (8)	0.0037 (7)
C6	0.0361 (8)	0.0481 (9)	0.0499 (10)	0.0051 (7)	0.0256 (8)	−0.0005 (7)
C7	0.0384 (8)	0.0429 (9)	0.0401 (8)	0.0013 (7)	0.0239 (7)	0.0018 (7)
C8	0.0383 (8)	0.0372 (8)	0.0423 (8)	0.0003 (6)	0.0269 (7)	0.0025 (6)
C9	0.0428 (9)	0.0437 (9)	0.0426 (9)	−0.0021 (7)	0.0283 (8)	0.0005 (7)
C10	0.0398 (8)	0.0441 (9)	0.0425 (9)	−0.0021 (7)	0.0269 (7)	−0.0040 (7)
C11	0.0496 (10)	0.0609 (11)	0.0510 (10)	−0.0022 (8)	0.0361 (9)	−0.0056 (8)
C12	0.0509 (10)	0.0683 (12)	0.0615 (11)	0.0072 (9)	0.0390 (10)	−0.0082 (10)
C13	0.0491 (10)	0.0542 (11)	0.0531 (11)	0.0109 (8)	0.0285 (9)	−0.0062 (8)
C14	0.0418 (9)	0.0406 (9)	0.0409 (9)	0.0016 (7)	0.0208 (8)	−0.0053 (7)
C15	0.0517 (10)	0.0373 (9)	0.0451 (9)	0.0026 (7)	0.0237 (8)	0.0027 (7)
C16	0.0535 (10)	0.0413 (9)	0.0455 (9)	−0.0059 (7)	0.0286 (9)	0.0033 (7)
C17	0.0441 (9)	0.0420 (9)	0.0480 (9)	−0.0035 (7)	0.0303 (8)	0.0005 (7)
C18	0.0360 (8)	0.0373 (8)	0.0377 (8)	−0.0022 (6)	0.0222 (7)	−0.0011 (6)
C19	0.0366 (8)	0.0386 (8)	0.0366 (8)	−0.0024 (6)	0.0214 (7)	−0.0045 (6)
C20	0.0382 (8)	0.0486 (9)	0.0388 (9)	0.0027 (7)	0.0226 (7)	0.0012 (7)
C21	0.0752 (14)	0.0593 (12)	0.0702 (13)	−0.0049 (10)	0.0475 (12)	−0.0184 (10)

Geometric parameters (Å, º) top

S3—C4	1.8044 (18)	C8—C9	1.570 (2)
S3—C2	1.8323 (18)	C9—C10	1.475 (2)
O22—C20	1.197 (2)	C10—C11	1.378 (2)
O23—C20	1.333 (2)	C10—C19	1.406 (2)
O23—C21	1.440 (2)	C11—C12	1.402 (3)
O24—C9	1.213 (2)	C11—H11	0.9300
N1—C2	1.451 (2)	C12—C13	1.371 (3)
N1—C8	1.478 (2)	C12—H12	0.9300
N1—C5	1.488 (2)	C13—C14	1.417 (2)
C2—H2A	0.9700	C13—H13	0.9300
C2—H2B	0.9700	C14—C19	1.405 (2)
C4—C5	1.527 (2)	C14—C15	1.420 (3)
C4—H4A	0.9700	C15—C16	1.366 (3)
C4—H4B	0.9700	C15—H15	0.9300
C5—C6	1.517 (2)	C16—C17	1.420 (2)
C5—H5	0.9800	C16—H16	0.9300
C6—C7	1.517 (2)	C17—C18	1.370 (2)
C6—H6A	0.9700	C17—H17	0.9300
C6—H6B	0.9700	C18—C19	1.409 (2)
C7—C20	1.501 (2)	C21—H21A	0.9600
C7—C8	1.556 (2)	C21—H21B	0.9600
C7—H7	0.9800	C21—H21C	0.9600
C8—C18	1.523 (2)

C4—S3—C2	86.99 (8)	O24—C9—C8	123.94 (15)
C20—O23—C21	116.51 (15)	C10—C9—C8	107.97 (13)
C2—N1—C8	119.47 (13)	C11—C10—C19	120.05 (16)
C2—N1—C5	111.25 (13)	C11—C10—C9	132.75 (16)
C8—N1—C5	110.46 (12)	C19—C10—C9	107.20 (13)
N1—C2—S3	107.44 (11)	C10—C11—C12	117.86 (17)
N1—C2—H2A	110.2	C10—C11—H11	121.1
S3—C2—H2A	110.2	C12—C11—H11	121.1
N1—C2—H2B	110.2	C13—C12—C11	122.68 (16)
S3—C2—H2B	110.2	C13—C12—H12	118.7
H2A—C2—H2B	108.5	C11—C12—H12	118.7
C5—C4—S3	105.92 (11)	C12—C13—C14	120.71 (17)
C5—C4—H4A	110.6	C12—C13—H13	119.6
S3—C4—H4A	110.6	C14—C13—H13	119.6
C5—C4—H4B	110.6	C19—C14—C13	116.15 (16)
S3—C4—H4B	110.6	C19—C14—C15	116.32 (15)
H4A—C4—H4B	108.7	C13—C14—C15	127.52 (16)
N1—C5—C6	104.44 (12)	C16—C15—C14	119.98 (16)
N1—C5—C4	108.56 (14)	C16—C15—H15	120.0
C6—C5—C4	114.91 (14)	C14—C15—H15	120.0
N1—C5—H5	109.6	C15—C16—C17	122.62 (16)
C6—C5—H5	109.6	C15—C16—H16	118.7
C4—C5—H5	109.6	C17—C16—H16	118.7
C7—C6—C5	102.89 (13)	C18—C17—C16	118.92 (15)
C7—C6—H6A	111.2	C18—C17—H17	120.5
C5—C6—H6A	111.2	C16—C17—H17	120.5
C7—C6—H6B	111.2	C17—C18—C19	118.37 (15)
C5—C6—H6B	111.2	C17—C18—C8	133.02 (14)
H6A—C6—H6B	109.1	C19—C18—C8	108.56 (13)
C20—C7—C6	114.87 (14)	C14—C19—C10	122.53 (15)
C20—C7—C8	113.49 (13)	C14—C19—C18	123.78 (15)
C6—C7—C8	103.50 (13)	C10—C19—C18	113.68 (14)
C20—C7—H7	108.2	O22—C20—O23	123.93 (16)
C6—C7—H7	108.2	O22—C20—C7	125.30 (16)
C8—C7—H7	108.2	O23—C20—C7	110.77 (14)
N1—C8—C18	116.20 (13)	O23—C21—H21A	109.5
N1—C8—C7	103.34 (12)	O23—C21—H21B	109.5
C18—C8—C7	116.12 (12)	H21A—C21—H21B	109.5
N1—C8—C9	107.46 (12)	O23—C21—H21C	109.5
C18—C8—C9	102.40 (12)	H21A—C21—H21C	109.5
C7—C8—C9	111.24 (13)	H21B—C21—H21C	109.5
O24—C9—C10	128.07 (15)

C8—N1—C2—S3	103.82 (13)	C19—C10—C11—C12	0.1 (3)
C5—N1—C2—S3	−26.76 (15)	C9—C10—C11—C12	−179.82 (18)
C4—S3—C2—N1	38.80 (12)	C10—C11—C12—C13	−0.9 (3)
C2—S3—C4—C5	−39.58 (12)	C11—C12—C13—C14	0.6 (3)
C2—N1—C5—C6	120.18 (15)	C12—C13—C14—C19	0.4 (3)
C8—N1—C5—C6	−14.93 (17)	C12—C13—C14—C15	178.87 (17)
C2—N1—C5—C4	−2.86 (18)	C19—C14—C15—C16	1.2 (2)
C8—N1—C5—C4	−137.97 (13)	C13—C14—C15—C16	−177.27 (17)
S3—C4—C5—N1	31.53 (15)	C14—C15—C16—C17	−0.9 (3)
S3—C4—C5—C6	−84.95 (15)	C15—C16—C17—C18	0.0 (3)
N1—C5—C6—C7	33.55 (16)	C16—C17—C18—C19	0.5 (2)
C4—C5—C6—C7	152.37 (14)	C16—C17—C18—C8	177.52 (16)
C5—C6—C7—C20	−163.65 (14)	N1—C8—C18—C17	−64.0 (2)
C5—C6—C7—C8	−39.38 (16)	C7—C8—C18—C17	57.9 (2)
C2—N1—C8—C18	−12.0 (2)	C9—C8—C18—C17	179.26 (17)
C5—N1—C8—C18	118.98 (14)	N1—C8—C18—C19	113.25 (14)
C2—N1—C8—C7	−140.33 (14)	C7—C8—C18—C19	−124.91 (14)
C5—N1—C8—C7	−9.40 (15)	C9—C8—C18—C19	−3.52 (16)
C2—N1—C8—C9	101.97 (15)	C13—C14—C19—C10	−1.2 (2)
C5—N1—C8—C9	−127.10 (13)	C15—C14—C19—C10	−179.85 (15)
C20—C7—C8—N1	155.29 (13)	C13—C14—C19—C18	177.99 (15)
C6—C7—C8—N1	30.13 (15)	C15—C14—C19—C18	−0.6 (2)
C20—C7—C8—C18	26.86 (19)	C11—C10—C19—C14	1.0 (2)
C6—C7—C8—C18	−98.30 (15)	C9—C10—C19—C14	−179.09 (14)
C20—C7—C8—C9	−89.70 (16)	C11—C10—C19—C18	−178.29 (15)
C6—C7—C8—C9	145.14 (13)	C9—C10—C19—C18	1.63 (19)
N1—C8—C9—O24	60.1 (2)	C17—C18—C19—C14	−0.2 (2)
C18—C8—C9—O24	−176.97 (16)	C8—C18—C19—C14	−177.89 (14)
C7—C8—C9—O24	−52.3 (2)	C17—C18—C19—C10	179.06 (14)
N1—C8—C9—C10	−118.42 (14)	C8—C18—C19—C10	1.38 (19)
C18—C8—C9—C10	4.47 (16)	C21—O23—C20—O22	1.3 (3)
C7—C8—C9—C10	129.15 (14)	C21—O23—C20—C7	−178.63 (15)
O24—C9—C10—C11	−2.4 (3)	C6—C7—C20—O22	1.1 (2)
C8—C9—C10—C11	176.05 (18)	C8—C7—C20—O22	−117.75 (19)
O24—C9—C10—C19	177.65 (17)	C6—C7—C20—O23	−179.05 (14)
C8—C9—C10—C19	−3.86 (17)	C8—C7—C20—O23	62.13 (18)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇NO₃S
M_r	339.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.3597 (1), 14.7896 (2), 14.9199 (1)
β (°)	128.660 (5)
V (Å³)	1612.73 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.93
Crystal size (mm)	0.32 × 0.20 × 0.18

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.583, 0.707
No. of measured, independent and observed [I > 2σ(I)] reflections	21038, 2926, 2567
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.104, 1.04
No. of reflections	2926
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.34

Computer programs: COLLECT (Nonius, 1997-2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), WinGX (Version 1.64.02; Farrugia, 1999) and PLATON (Spek, 2002), SHELXL97.

Selected geometric parameters (Å, º) top

C6—C7	1.517 (2)

C2—N1—C8	119.47 (13)	C8—N1—C5	110.46 (12)
C2—N1—C5	111.25 (13)	C7—C6—C5	102.89 (13)

N1—C5—C6—C7	33.55 (16)	C5—C6—C7—C20	−163.65 (14)
C4—C5—C6—C7	152.37 (14)	C6—C7—C8—N1	30.13 (15)

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(rac-5RS,7RS,8SR)-Spiro­[7-methoxy­carbonyl-1-aza-3-thia­bi­cyclo­[3.3.0]­octane-8,1'-ace­naphthyl­en]-2'-one