Crystal structure of methyl 7-phenyl-6a,7,7a,8,9,10-hexa-hydro-6H,11aH-thio-chromeno[3,4-b]pyrrolizine-6a--carbox-ylate.

In the title compound, C22H23NO2S, the inner pyrrolidine ring (A) adopts an envelope conformation with the methine C atom opposite the fused C-N bond as the flap. The thio-pyran ring (C) has a half-chair conformation and its mean plane is inclined to the fused benzene ring by 1.74 (11)°, and by 60.52 (11)° to the mean plane of pyrrolidine ring A. In the outer pyrrolidine ring (B), the C atom opposite the fused C-N bond is disordered [site-occupancy ratio = 0.427 (13):0.573 (13)] and both rings have envelope conformations, with the disordered C atom as the flap. The planes of the phenyl ring and the benzene ring of the thio-chromane unit are inclined to one another by 65.52 (14)°. In the crystal, mol-ecules are linked by a pair of C-H⋯O hydrogen bonds forming inversion dimers.

Related literature

For the biological activity of pyrrolizine derivatives, see: Raj et al. (2003 ▸); Atal (1978 ▸); Denny (2001 ▸); Suzuki et al. (1994 ▸). For a related structure, see: Ramesh et al. (2007 ▸).

Experimental

Crystal data

C22H23NO2S

M = 365.47

Triclinic,

a = 9.5184 (4) Å

b = 10.4041 (5) Å

c = 10.6923 (4) Å

α = 81.270 (2)°

β = 66.626 (2)°

γ = 74.385 (2)°

V = 934.88 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.30 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.945, T max = 0.954

18019 measured reflections

3265 independent reflections

2504 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.03

3265 reflections

246 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; 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 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015014024/su5170sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014024/su5170Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015014024/su5170Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015014024/su5170fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015014024/su5170fig2.tif

The crystal packing of the title compound, viewed along the a axis. Dashed lines shows the inter­molecular C-H⋯O hydrogen bonds (see Table 1). H atoms not involved in hydrogen bonding have been omitted for clarity.

CCDC reference: 1414784

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H23NO2S	Z = 2
Mr = 365.47	F(000) = 388
Triclinic, P1	Dx = 1.298 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5184 (4) Å	Cell parameters from 3265 reflections
b = 10.4041 (5) Å	θ = 2.1–25.0°
c = 10.6923 (4) Å	µ = 0.19 mm−1
α = 81.270 (2)°	T = 293 K
β = 66.626 (2)°	Block, colourless
γ = 74.385 (2)°	0.30 × 0.30 × 0.25 mm
V = 934.88 (7) Å3

Bruker Kappa APEXII CCD diffractometer	3265 independent reflections
Radiation source: fine-focus sealed tube	2504 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.945, Tmax = 0.954	k = −12→12
18019 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.112	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.4695P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3265 reflections	Δρmax = 0.21 e Å−3
246 parameters	Δρmin = −0.21 e Å−3
10 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
C1	0.9603 (3)	0.3962 (4)	0.3621 (3)	0.0705 (8)
H1	1.0279	0.4231	0.2778	0.085*
C2	0.9631 (3)	0.2640 (3)	0.3945 (3)	0.0702 (8)
H2	1.0334	0.2005	0.3328	0.084*
C3	0.8613 (3)	0.2244 (3)	0.5191 (2)	0.0541 (6)
H3	0.8631	0.1341	0.5402	0.065*
C4	0.7568 (2)	0.3172 (2)	0.6132 (2)	0.0417 (5)
C5	0.7572 (3)	0.4499 (2)	0.5783 (2)	0.0535 (6)
H5	0.6883	0.5142	0.6397	0.064*
C6	0.8587 (3)	0.4888 (3)	0.4532 (3)	0.0655 (7)
H6	0.8574	0.5790	0.4312	0.079*
C7	0.6470 (2)	0.2688 (2)	0.74667 (19)	0.0383 (5)
H7	0.6321	0.1845	0.7293	0.046*
C8	0.4827 (2)	0.3576 (2)	0.8094 (2)	0.0488 (6)
H8	0.4892	0.4514	0.7964	0.059*
C9	0.3619 (3)	0.3412 (4)	0.7578 (3)	0.0890 (11)
H9A	0.3418	0.4164	0.6965	0.107*	0.427 (13)
H9B	0.4002	0.2600	0.7085	0.107*	0.427 (13)
H9C	0.2928	0.4264	0.7482	0.107*	0.573 (13)
H9D	0.4119	0.2990	0.6710	0.107*	0.573 (13)
C10	0.2151 (9)	0.3342 (11)	0.8782 (7)	0.057 (2)	0.427 (13)
H10A	0.1624	0.2720	0.8659	0.069*	0.427 (13)
H10B	0.1432	0.4214	0.8954	0.069*	0.427 (13)
C10'	0.2769 (10)	0.2563 (10)	0.8649 (7)	0.091 (2)	0.573 (13)
H10C	0.1701	0.2721	0.8687	0.109*	0.573 (13)
H10D	0.3275	0.1631	0.8465	0.109*	0.573 (13)
C11	0.2750 (3)	0.2854 (3)	0.9919 (3)	0.0691 (8)
H11A	0.2000	0.3268	1.0756	0.083*	0.427 (13)
H11B	0.2873	0.1894	1.0068	0.083*	0.427 (13)
H11C	0.2653	0.2084	1.0558	0.083*	0.573 (13)
H11D	0.1886	0.3601	1.0319	0.083*	0.573 (13)
C12	0.5497 (2)	0.21009 (19)	0.98166 (19)	0.0364 (5)
H12	0.5360	0.1253	0.9643	0.044*
C13	0.5386 (2)	0.2033 (2)	1.1270 (2)	0.0407 (5)
C14	0.4304 (3)	0.1386 (3)	1.2261 (2)	0.0595 (6)
H14	0.3685	0.1005	1.2005	0.071*
C15	0.4123 (4)	0.1294 (3)	1.3608 (3)	0.0781 (8)
H15	0.3387	0.0858	1.4254	0.094*
C16	0.5026 (4)	0.1842 (3)	1.3991 (3)	0.0767 (9)
H16	0.4899	0.1786	1.4905	0.092*
C17	0.6118 (3)	0.2473 (3)	1.3047 (2)	0.0611 (7)
H17	0.6728	0.2845	1.3323	0.073*
C18	0.6326 (3)	0.2566 (2)	1.1671 (2)	0.0450 (5)
C19	0.7422 (2)	0.35732 (19)	0.9027 (2)	0.0398 (5)
H19A	0.6539	0.4339	0.9156	0.048*
H19B	0.8314	0.3793	0.8260	0.048*
C20	0.7012 (2)	0.23802 (18)	0.87029 (19)	0.0339 (4)
C21	0.8360 (2)	0.1159 (2)	0.8429 (2)	0.0395 (5)
C22	1.1091 (3)	0.0345 (3)	0.7589 (3)	0.0748 (8)
H22A	1.2034	0.0674	0.7209	0.112*
H22B	1.1072	−0.0189	0.6941	0.112*
H22C	1.1068	−0.0189	0.8409	0.112*
N1	0.42652 (18)	0.31903 (18)	0.95607 (17)	0.0428 (4)
O1	0.8198 (2)	0.00459 (16)	0.8592 (2)	0.0818 (6)
O2	0.97460 (16)	0.14517 (15)	0.78985 (17)	0.0542 (4)
S1	0.78888 (7)	0.32480 (6)	1.05291 (6)	0.0536 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0631 (17)	0.108 (2)	0.0412 (14)	−0.0378 (17)	−0.0105 (12)	0.0030 (15)
C2	0.0528 (15)	0.103 (2)	0.0478 (15)	−0.0215 (15)	−0.0017 (12)	−0.0246 (15)
C3	0.0475 (13)	0.0635 (15)	0.0458 (13)	−0.0114 (11)	−0.0091 (11)	−0.0121 (11)
C4	0.0354 (11)	0.0533 (13)	0.0355 (11)	−0.0070 (10)	−0.0147 (9)	−0.0018 (10)
C5	0.0506 (13)	0.0552 (15)	0.0470 (13)	−0.0061 (11)	−0.0162 (11)	0.0030 (11)
C6	0.0671 (17)	0.0736 (18)	0.0585 (16)	−0.0253 (15)	−0.0279 (14)	0.0176 (14)
C7	0.0363 (10)	0.0405 (11)	0.0365 (11)	−0.0051 (9)	−0.0130 (9)	−0.0056 (9)
C8	0.0350 (11)	0.0623 (15)	0.0406 (12)	−0.0016 (10)	−0.0121 (9)	−0.0007 (10)
C9	0.0467 (15)	0.157 (3)	0.0638 (18)	0.0036 (19)	−0.0299 (14)	−0.028 (2)
C10	0.035 (4)	0.066 (5)	0.074 (4)	−0.010 (3)	−0.021 (3)	−0.015 (4)
C10'	0.054 (4)	0.097 (6)	0.143 (6)	−0.006 (4)	−0.047 (4)	−0.057 (5)
C11	0.0339 (12)	0.0849 (19)	0.0797 (19)	−0.0148 (13)	−0.0153 (12)	0.0063 (15)
C12	0.0365 (10)	0.0324 (10)	0.0383 (11)	−0.0071 (8)	−0.0112 (9)	−0.0050 (8)
C13	0.0413 (11)	0.0363 (11)	0.0361 (11)	0.0000 (9)	−0.0103 (9)	−0.0053 (9)
C14	0.0585 (15)	0.0644 (16)	0.0444 (14)	−0.0149 (13)	−0.0089 (11)	0.0015 (12)
C15	0.083 (2)	0.087 (2)	0.0419 (15)	−0.0166 (17)	−0.0062 (14)	0.0051 (14)
C16	0.093 (2)	0.081 (2)	0.0349 (14)	0.0101 (17)	−0.0200 (15)	−0.0067 (13)
C17	0.0727 (17)	0.0586 (15)	0.0491 (15)	0.0103 (13)	−0.0314 (13)	−0.0163 (12)
C18	0.0486 (12)	0.0380 (12)	0.0425 (12)	0.0068 (10)	−0.0190 (10)	−0.0105 (9)
C19	0.0394 (11)	0.0328 (11)	0.0467 (12)	−0.0076 (9)	−0.0149 (9)	−0.0048 (9)
C20	0.0328 (10)	0.0310 (10)	0.0367 (10)	−0.0049 (8)	−0.0123 (8)	−0.0047 (8)
C21	0.0376 (11)	0.0351 (12)	0.0432 (12)	−0.0045 (9)	−0.0131 (9)	−0.0070 (9)
C22	0.0391 (13)	0.0678 (18)	0.108 (2)	0.0126 (12)	−0.0237 (14)	−0.0337 (16)
N1	0.0315 (9)	0.0497 (11)	0.0400 (10)	−0.0050 (8)	−0.0089 (7)	−0.0015 (8)
O1	0.0528 (10)	0.0327 (10)	0.1383 (19)	−0.0052 (8)	−0.0149 (11)	−0.0088 (10)
O2	0.0325 (8)	0.0463 (9)	0.0772 (11)	−0.0004 (7)	−0.0141 (7)	−0.0175 (8)
S1	0.0555 (4)	0.0559 (4)	0.0602 (4)	−0.0130 (3)	−0.0294 (3)	−0.0123 (3)

C1—C6	1.360 (4)	C11—H11A	0.9700
C1—C2	1.362 (4)	C11—H11B	0.9700
C1—H1	0.9300	C11—H11C	0.9700
C2—C3	1.381 (3)	C11—H11D	0.9700
C2—H2	0.9300	C12—N1	1.476 (3)
C3—C4	1.384 (3)	C12—C13	1.507 (3)
C3—H3	0.9300	C12—C20	1.530 (3)
C4—C5	1.375 (3)	C12—H12	0.9800
C4—C7	1.505 (3)	C13—C14	1.388 (3)
C5—C6	1.381 (3)	C13—C18	1.392 (3)
C5—H5	0.9300	C14—C15	1.373 (4)
C6—H6	0.9300	C14—H14	0.9300
C7—C8	1.526 (3)	C15—C16	1.359 (4)
C7—C20	1.562 (3)	C15—H15	0.9300
C7—H7	0.9800	C16—C17	1.366 (4)
C8—N1	1.472 (3)	C16—H16	0.9300
C8—C9	1.514 (3)	C17—C18	1.396 (3)
C8—H8	0.9800	C17—H17	0.9300
C9—C10'	1.445 (8)	C18—S1	1.752 (2)
C9—C10	1.488 (7)	C19—C20	1.520 (3)
C9—H9A	0.9700	C19—S1	1.793 (2)
C9—H9B	0.9700	C19—H19A	0.9700
C9—H9C	0.9700	C19—H19B	0.9700
C9—H9D	0.9700	C20—C21	1.511 (3)
C10—C11	1.506 (7)	C21—O1	1.187 (2)
C10—H10A	0.9700	C21—O2	1.313 (2)
C10—H10B	0.9700	C22—O2	1.435 (3)
C10'—C11	1.428 (6)	C22—H22A	0.9600
C10'—H10C	0.9700	C22—H22B	0.9600
C10'—H10D	0.9700	C22—H22C	0.9600
C11—N1	1.463 (3)
C6—C1—C2	119.9 (2)	N1—C11—H11A	109.7
C6—C1—H1	120.1	C10—C11—H11A	109.7
C2—C1—H1	120.1	C10'—C11—H11B	81.2
C1—C2—C3	120.0 (3)	N1—C11—H11B	109.7
C1—C2—H2	120.0	C10—C11—H11B	109.7
C3—C2—H2	120.0	H11A—C11—H11B	108.2
C2—C3—C4	121.0 (2)	C10'—C11—H11C	110.9
C2—C3—H3	119.5	N1—C11—H11C	110.9
C4—C3—H3	119.5	C10—C11—H11C	132.3
C5—C4—C3	117.9 (2)	H11A—C11—H11C	78.6
C5—C4—C7	123.32 (19)	H11B—C11—H11C	31.7
C3—C4—C7	118.8 (2)	C10'—C11—H11D	110.9
C4—C5—C6	120.9 (2)	N1—C11—H11D	110.9
C4—C5—H5	119.6	C10—C11—H11D	78.1
C6—C5—H5	119.6	H11A—C11—H11D	33.9
C1—C6—C5	120.4 (3)	H11B—C11—H11D	132.5
C1—C6—H6	119.8	H11C—C11—H11D	108.9
C5—C6—H6	119.8	N1—C12—C13	111.97 (15)
C4—C7—C8	117.60 (17)	N1—C12—C20	102.97 (15)
C4—C7—C20	117.97 (16)	C13—C12—C20	116.79 (16)
C8—C7—C20	101.70 (15)	N1—C12—H12	108.2
C4—C7—H7	106.2	C13—C12—H12	108.2
C8—C7—H7	106.2	C20—C12—H12	108.2
C20—C7—H7	106.2	C14—C13—C18	118.1 (2)
N1—C8—C9	106.7 (2)	C14—C13—C12	118.3 (2)
N1—C8—C7	105.94 (16)	C18—C13—C12	123.55 (19)
C9—C8—C7	115.6 (2)	C15—C14—C13	121.7 (3)
N1—C8—H8	109.5	C15—C14—H14	119.1
C9—C8—H8	109.5	C13—C14—H14	119.1
C7—C8—H8	109.5	C16—C15—C14	119.6 (3)
C10'—C9—C10	34.0 (3)	C16—C15—H15	120.2
C10'—C9—C8	102.1 (3)	C14—C15—H15	120.2
C10—C9—C8	107.7 (3)	C15—C16—C17	120.6 (2)
C10'—C9—H9A	139.4	C15—C16—H16	119.7
C10—C9—H9A	110.2	C17—C16—H16	119.7
C8—C9—H9A	110.2	C16—C17—C18	120.6 (3)
C10'—C9—H9B	81.7	C16—C17—H17	119.7
C10—C9—H9B	110.2	C18—C17—H17	119.7
C8—C9—H9B	110.2	C13—C18—C17	119.4 (2)
H9A—C9—H9B	108.5	C13—C18—S1	123.83 (16)
C10'—C9—H9C	111.0	C17—C18—S1	116.60 (19)
C10—C9—H9C	78.1	C20—C19—S1	111.91 (14)
C8—C9—H9C	111.4	C20—C19—H19A	109.2
H9A—C9—H9C	33.9	S1—C19—H19A	109.2
H9B—C9—H9C	132.2	C20—C19—H19B	109.2
C10'—C9—H9D	111.6	S1—C19—H19B	109.2
C10—C9—H9D	133.3	H19A—C19—H19B	107.9
C8—C9—H9D	111.3	C21—C20—C19	112.36 (16)
H9A—C9—H9D	79.2	C21—C20—C12	112.39 (16)
H9B—C9—H9D	31.5	C19—C20—C12	110.86 (16)
H9C—C9—H9D	109.2	C21—C20—C7	108.94 (15)
C9—C10—C11	102.6 (5)	C19—C20—C7	112.48 (16)
C9—C10—H10A	111.2	C12—C20—C7	99.11 (14)
C11—C10—H10A	111.2	O1—C21—O2	122.81 (19)
C9—C10—H10B	111.2	O1—C21—C20	123.89 (19)
C11—C10—H10B	111.2	O2—C21—C20	113.15 (17)
H10A—C10—H10B	109.2	O2—C22—H22A	109.5
C11—C10'—C9	108.8 (4)	O2—C22—H22B	109.5
C11—C10'—H10C	109.9	H22A—C22—H22B	109.5
C9—C10'—H10C	109.9	O2—C22—H22C	109.5
C11—C10'—H10D	109.9	H22A—C22—H22C	109.5
C9—C10'—H10D	109.9	H22B—C22—H22C	109.5
H10C—C10'—H10D	108.3	C11—N1—C8	107.08 (18)
C10'—C11—N1	104.2 (3)	C11—N1—C12	115.18 (18)
C10'—C11—C10	33.9 (3)	C8—N1—C12	108.21 (15)
N1—C11—C10	109.6 (3)	C21—O2—C22	116.65 (18)
C10'—C11—H11A	138.5	C18—S1—C19	101.43 (10)
C6—C1—C2—C3	0.8 (4)	C16—C17—C18—C13	1.4 (3)
C1—C2—C3—C4	−0.7 (4)	C16—C17—C18—S1	−173.83 (19)
C2—C3—C4—C5	0.2 (3)	S1—C19—C20—C21	−61.3 (2)
C2—C3—C4—C7	179.2 (2)	S1—C19—C20—C12	65.39 (18)
C3—C4—C5—C6	0.1 (3)	S1—C19—C20—C7	175.32 (13)
C7—C4—C5—C6	−178.8 (2)	N1—C12—C20—C21	−159.41 (15)
C2—C1—C6—C5	−0.4 (4)	C13—C12—C20—C21	77.5 (2)
C4—C5—C6—C1	0.0 (4)	N1—C12—C20—C19	73.91 (18)
C5—C4—C7—C8	33.6 (3)	C13—C12—C20—C19	−49.2 (2)
C3—C4—C7—C8	−145.3 (2)	N1—C12—C20—C7	−44.48 (17)
C5—C4—C7—C20	−88.8 (2)	C13—C12—C20—C7	−167.61 (16)
C3—C4—C7—C20	92.3 (2)	C4—C7—C20—C21	−68.8 (2)
C4—C7—C8—N1	−157.46 (17)	C8—C7—C20—C21	160.99 (17)
C20—C7—C8—N1	−27.0 (2)	C4—C7—C20—C19	56.5 (2)
C4—C7—C8—C9	84.7 (3)	C8—C7—C20—C19	−73.7 (2)
C20—C7—C8—C9	−144.9 (2)	C4—C7—C20—C12	173.63 (17)
N1—C8—C9—C10'	−17.6 (5)	C8—C7—C20—C12	43.42 (19)
C7—C8—C9—C10'	99.9 (5)	C19—C20—C21—O1	154.4 (2)
N1—C8—C9—C10	17.1 (6)	C12—C20—C21—O1	28.6 (3)
C7—C8—C9—C10	134.6 (5)	C7—C20—C21—O1	−80.2 (3)
C10'—C9—C10—C11	60.9 (6)	C19—C20—C21—O2	−30.0 (2)
C8—C9—C10—C11	−24.5 (7)	C12—C20—C21—O2	−155.88 (17)
C10—C9—C10'—C11	−71.8 (7)	C7—C20—C21—O2	95.31 (19)
C8—C9—C10'—C11	32.0 (7)	C10'—C11—N1—C8	21.1 (5)
C9—C10'—C11—N1	−33.9 (7)	C10—C11—N1—C8	−13.9 (5)
C9—C10'—C11—C10	70.2 (8)	C10'—C11—N1—C12	−99.3 (5)
C9—C10—C11—C10'	−62.4 (7)	C10—C11—N1—C12	−134.3 (5)
C9—C10—C11—N1	23.8 (7)	C9—C8—N1—C11	−1.9 (3)
N1—C12—C13—C14	81.6 (2)	C7—C8—N1—C11	−125.6 (2)
C20—C12—C13—C14	−160.09 (19)	C9—C8—N1—C12	122.8 (2)
N1—C12—C13—C18	−99.5 (2)	C7—C8—N1—C12	−0.9 (2)
C20—C12—C13—C18	18.9 (3)	C13—C12—N1—C11	−84.8 (2)
C18—C13—C14—C15	1.6 (3)	C20—C12—N1—C11	148.95 (19)
C12—C13—C14—C15	−179.4 (2)	C13—C12—N1—C8	155.49 (18)
C13—C14—C15—C16	−0.3 (4)	C20—C12—N1—C8	29.2 (2)
C14—C15—C16—C17	−0.5 (4)	O1—C21—O2—C22	−3.5 (3)
C15—C16—C17—C18	0.0 (4)	C20—C21—O2—C22	−179.14 (19)
C14—C13—C18—C17	−2.1 (3)	C13—C18—S1—C19	19.2 (2)
C12—C13—C18—C17	178.92 (18)	C17—C18—S1—C19	−165.83 (16)
C14—C13—C18—S1	172.73 (16)	C20—C19—S1—C18	−47.73 (16)
C12—C13—C18—S1	−6.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···O1i	0.97	2.48	3.365 (3)	151

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C11H11CO1i	0.97	2.48	3.365(3)	151

Symmetry code: (i) .