Ethyl (E)-3-[1'-ethyl-2-oxo-4'-(phenyl-sulfon-yl)-2H-spiro-[acenaphthyl-ene-1,2'-pyrrolidine]-3'-yl]acrylate.

In the title compound, C(28)H(27)NO(5)S, the five-membered pyrrolidine ring, which exhibits an envelope conformation (the C atom at the spiral junction being the flap atom), makes dihedral angles of 57.37 (10) and 86.84 (8)°, respectively, with the phenyl ring and the acenaphthyl-ene ring system. In the crystal, mol-ecules associate via two C-H⋯O hydrogen bonds, forming R(2) (2)(20) and R(2) (2)(10) graph-set motifs.

Related literature

For the biological activity of spiro compounds, see: Kobayashi et al. (1991 ▶); James et al. (1991 ▶); Obniska et al. (2003 ▶); Peddi et al. (2004 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C28H27NO5S

M = 489.58

Triclinic,

a = 11.1917 (8) Å

b = 11.7778 (9) Å

c = 12.1511 (9) Å

α = 93.572 (3)°

β = 115.911 (3)°

γ = 114.134 (3)°

V = 1256.82 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 295 K

0.26 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.957, T max = 0.967

19294 measured reflections

6053 independent reflections

4834 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.127

S = 1.04

6053 reflections

318 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812016042/rk2349sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016042/rk2349Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812016042/rk2349Isup3.cml

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

C28H27NO5S	Z = 2
Mr = 489.58	F(000) = 516
Triclinic, P1	Dx = 1.294 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.1917 (8) Å	Cell parameters from 1225 reflections
b = 11.7778 (9) Å	θ = 2.0–28.3°
c = 12.1511 (9) Å	µ = 0.17 mm−1
α = 93.572 (3)°	T = 295 K
β = 115.911 (3)°	Block, colourless
γ = 114.134 (3)°	0.26 × 0.23 × 0.20 mm
V = 1256.82 (17) Å3

Bruker SMART APEXII CCD diffractometer	6053 independent reflections
Radiation source: fine–focus sealed tube	4834 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
Tmin = 0.957, Tmax = 0.967	k = −13→15
19294 measured reflections	l = −16→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0631P)2 + 0.2849P] where P = (Fo2 + 2Fc2)/3
6053 reflections	(Δ/σ)max < 0.001
318 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.30 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 > σ(F2) is used only for calculating R–factors(gt) etc. and is not relevant to the choice o f 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	1.2133 (2)	0.56954 (17)	1.03581 (16)	0.0564 (4)
H1	1.1535	0.6095	1.0209	0.068*
C2	1.3587 (2)	0.6248 (2)	1.14553 (18)	0.0677 (5)
H2	1.3955	0.7031	1.2030	0.081*
C3	1.4474 (2)	0.5662 (2)	1.16999 (17)	0.0661 (5)
H3	1.5428	0.6057	1.2438	0.079*
C4	1.39774 (18)	0.44698 (17)	1.08589 (14)	0.0515 (4)
C5	1.25279 (16)	0.39499 (15)	0.97617 (13)	0.0423 (3)
C6	1.16211 (17)	0.45494 (15)	0.95136 (14)	0.0441 (3)
C7	1.02002 (16)	0.37311 (15)	0.82823 (14)	0.0420 (3)
C8	1.02678 (15)	0.24970 (14)	0.78074 (13)	0.0385 (3)
C9	1.18392 (16)	0.27742 (14)	0.88182 (13)	0.0410 (3)
C10	1.26179 (18)	0.21055 (17)	0.89651 (16)	0.0515 (4)
H10	1.2195	0.1328	0.8356	0.062*
C11	1.4085 (2)	0.2614 (2)	1.00628 (18)	0.0601 (4)
H11	1.4614	0.2155	1.0160	0.072*
C12	1.47483 (19)	0.3748 (2)	1.09791 (16)	0.0596 (5)
H12	1.5711	0.4047	1.1685	0.071*
C13	0.8902 (2)	0.12685 (18)	0.88435 (17)	0.0578 (4)
H13A	0.8506	0.1842	0.8929	0.069*
H13B	0.9899	0.1599	0.9595	0.069*
C14	0.7862 (3)	−0.0082 (2)	0.8781 (2)	0.0868 (7)
H14A	0.6855	−0.0386	0.8075	0.130*
H14B	0.7842	−0.0057	0.9564	0.130*
H14C	0.8230	−0.0660	0.8664	0.130*
C15	0.76449 (17)	0.09965 (17)	0.65328 (15)	0.0534 (4)
H15A	0.7127	0.1405	0.6712	0.064*
H15B	0.6962	0.0066	0.6163	0.064*
C16	0.81788 (15)	0.15707 (14)	0.56245 (13)	0.0407 (3)
H16	0.7847	0.2215	0.5388	0.049*
C17	0.99379 (15)	0.22744 (13)	0.64103 (13)	0.0368 (3)
H17	1.0283	0.1673	0.6250	0.044*
C18	1.06771 (15)	0.34865 (13)	0.60997 (12)	0.0370 (3)
H18	1.0383	0.4115	0.6131	0.044*
C19	1.17266 (15)	0.37120 (14)	0.57825 (13)	0.0389 (3)
H19	1.2063	0.3110	0.5778	0.047*
C20	1.23705 (16)	0.49004 (15)	0.54361 (14)	0.0414 (3)
C21	1.3948 (2)	0.5929 (2)	0.4584 (2)	0.0715 (6)
H21A	1.3187	0.6174	0.4098	0.086*
H21B	1.4236	0.5647	0.4018	0.086*
C22	1.5286 (3)	0.7062 (2)	0.5650 (4)	0.1173 (11)
H22A	1.4980	0.7406	0.6154	0.176*
H22B	1.5749	0.7718	0.5319	0.176*
H22C	1.6003	0.6803	0.6176	0.176*
C23	0.81600 (17)	0.11501 (15)	0.33263 (14)	0.0450 (3)
C24	0.7631 (2)	0.1943 (2)	0.27206 (18)	0.0645 (5)
H24	0.6808	0.1973	0.2709	0.077*
C25	0.8334 (3)	0.2684 (3)	0.2137 (2)	0.0886 (7)
H25	0.7995	0.3228	0.1740	0.106*
C26	0.9531 (3)	0.2626 (3)	0.2136 (2)	0.0865 (7)
H26	1.0004	0.3135	0.1744	0.104*
C27	1.0036 (2)	0.1820 (2)	0.2713 (2)	0.0739 (6)
H27	1.0832	0.1769	0.2689	0.089*
C28	0.9364 (2)	0.10824 (18)	0.33293 (17)	0.0564 (4)
H28	0.9718	0.0551	0.3738	0.068*
N1	0.90471 (14)	0.12794 (12)	0.77021 (12)	0.0458 (3)
O1	0.91411 (13)	0.39290 (12)	0.77286 (11)	0.0570 (3)
O2	1.20878 (15)	0.57760 (12)	0.54698 (14)	0.0612 (3)
O3	1.33098 (13)	0.48649 (11)	0.50468 (12)	0.0549 (3)
O4	0.57643 (13)	−0.01410 (13)	0.35199 (13)	0.0698 (4)
O5	0.78909 (16)	−0.06088 (11)	0.45257 (13)	0.0680 (4)
S1	0.73711 (4)	0.03210 (4)	0.41992 (4)	0.04772 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0689 (11)	0.0555 (10)	0.0484 (9)	0.0283 (9)	0.0346 (8)	0.0137 (8)
C2	0.0720 (12)	0.0613 (11)	0.0463 (9)	0.0173 (10)	0.0278 (9)	−0.0002 (8)
C3	0.0547 (10)	0.0728 (12)	0.0385 (8)	0.0146 (9)	0.0155 (8)	0.0035 (8)
C4	0.0432 (8)	0.0612 (10)	0.0355 (7)	0.0160 (7)	0.0171 (6)	0.0156 (7)
C5	0.0405 (7)	0.0466 (8)	0.0346 (7)	0.0155 (6)	0.0196 (6)	0.0162 (6)
C6	0.0487 (8)	0.0464 (8)	0.0374 (7)	0.0201 (7)	0.0245 (6)	0.0152 (6)
C7	0.0440 (7)	0.0482 (8)	0.0390 (7)	0.0225 (7)	0.0242 (6)	0.0190 (6)
C8	0.0356 (7)	0.0390 (7)	0.0366 (7)	0.0151 (6)	0.0171 (6)	0.0151 (6)
C9	0.0385 (7)	0.0427 (7)	0.0364 (7)	0.0167 (6)	0.0171 (6)	0.0169 (6)
C10	0.0489 (8)	0.0492 (9)	0.0508 (9)	0.0242 (7)	0.0204 (7)	0.0176 (7)
C11	0.0498 (9)	0.0730 (12)	0.0603 (10)	0.0359 (9)	0.0230 (8)	0.0315 (10)
C12	0.0404 (8)	0.0778 (12)	0.0447 (9)	0.0239 (8)	0.0131 (7)	0.0228 (9)
C13	0.0596 (10)	0.0599 (10)	0.0485 (9)	0.0185 (8)	0.0319 (8)	0.0239 (8)
C14	0.0939 (16)	0.0752 (14)	0.0774 (14)	0.0158 (12)	0.0540 (13)	0.0389 (12)
C15	0.0374 (7)	0.0598 (10)	0.0474 (8)	0.0108 (7)	0.0207 (7)	0.0195 (8)
C16	0.0334 (6)	0.0406 (7)	0.0392 (7)	0.0133 (6)	0.0156 (6)	0.0131 (6)
C17	0.0333 (6)	0.0363 (7)	0.0355 (6)	0.0140 (5)	0.0158 (5)	0.0123 (5)
C18	0.0344 (6)	0.0368 (7)	0.0339 (6)	0.0145 (5)	0.0151 (5)	0.0122 (5)
C19	0.0332 (6)	0.0379 (7)	0.0386 (7)	0.0147 (6)	0.0152 (6)	0.0113 (6)
C20	0.0352 (7)	0.0451 (8)	0.0433 (7)	0.0182 (6)	0.0202 (6)	0.0161 (6)
C21	0.0734 (12)	0.0852 (14)	0.0947 (15)	0.0458 (11)	0.0623 (12)	0.0546 (13)
C22	0.0925 (19)	0.0644 (15)	0.186 (3)	0.0142 (14)	0.086 (2)	0.0329 (18)
C23	0.0461 (8)	0.0407 (8)	0.0350 (7)	0.0187 (6)	0.0134 (6)	0.0051 (6)
C24	0.0807 (13)	0.0763 (13)	0.0578 (10)	0.0510 (11)	0.0382 (10)	0.0317 (10)
C25	0.132 (2)	0.0989 (17)	0.0813 (15)	0.0738 (17)	0.0701 (16)	0.0562 (14)
C26	0.1058 (18)	0.0906 (16)	0.0697 (13)	0.0378 (15)	0.0579 (14)	0.0316 (12)
C27	0.0615 (11)	0.0879 (15)	0.0614 (11)	0.0273 (11)	0.0338 (10)	0.0014 (11)
C28	0.0532 (9)	0.0541 (10)	0.0500 (9)	0.0267 (8)	0.0178 (8)	0.0031 (8)
N1	0.0395 (6)	0.0447 (7)	0.0412 (6)	0.0105 (5)	0.0197 (5)	0.0180 (5)
O1	0.0546 (7)	0.0699 (8)	0.0529 (7)	0.0385 (6)	0.0244 (6)	0.0199 (6)
O2	0.0699 (8)	0.0539 (7)	0.0907 (9)	0.0373 (6)	0.0559 (7)	0.0374 (7)
O3	0.0505 (6)	0.0576 (7)	0.0732 (8)	0.0278 (5)	0.0415 (6)	0.0305 (6)
O4	0.0377 (6)	0.0700 (8)	0.0584 (7)	0.0078 (6)	0.0094 (5)	0.0079 (6)
O5	0.0770 (9)	0.0391 (6)	0.0711 (8)	0.0264 (6)	0.0260 (7)	0.0188 (6)
S1	0.0393 (2)	0.0385 (2)	0.0427 (2)	0.01109 (16)	0.01077 (16)	0.00891 (15)

C1—C6	1.373 (2)	C15—H15B	0.9700
C1—C2	1.406 (3)	C16—C17	1.5488 (18)
C1—H1	0.9300	C16—S1	1.7914 (16)
C2—C3	1.371 (3)	C16—H16	0.9800
C2—H2	0.9300	C17—C18	1.4963 (18)
C3—C4	1.418 (3)	C17—H17	0.9800
C3—H3	0.9300	C18—C19	1.3236 (19)
C4—C5	1.407 (2)	C18—H18	0.9300
C4—C12	1.412 (3)	C19—C20	1.473 (2)
C5—C6	1.402 (2)	C19—H19	0.9300
C5—C9	1.408 (2)	C20—O2	1.1993 (19)
C6—C7	1.478 (2)	C20—O3	1.3411 (18)
C7—O1	1.2085 (18)	C21—O3	1.451 (2)
C7—C8	1.573 (2)	C21—C22	1.468 (4)
C8—N1	1.4703 (17)	C21—H21A	0.9700
C8—C9	1.5168 (19)	C21—H21B	0.9700
C8—C17	1.5506 (19)	C22—H22A	0.9600
C9—C10	1.362 (2)	C22—H22B	0.9600
C10—C11	1.420 (2)	C22—H22C	0.9600
C10—H10	0.9300	C23—C28	1.381 (2)
C11—C12	1.363 (3)	C23—C24	1.386 (2)
C11—H11	0.9300	C23—S1	1.7609 (16)
C12—H12	0.9300	C24—C25	1.373 (3)
C13—N1	1.465 (2)	C24—H24	0.9300
C13—C14	1.511 (3)	C25—C26	1.369 (4)
C13—H13A	0.9700	C25—H25	0.9300
C13—H13B	0.9700	C26—C27	1.373 (3)
C14—H14A	0.9600	C26—H26	0.9300
C14—H14B	0.9600	C27—C28	1.386 (3)
C14—H14C	0.9600	C27—H27	0.9300
C15—N1	1.469 (2)	C28—H28	0.9300
C15—C16	1.540 (2)	O4—S1	1.4345 (12)
C15—H15A	0.9700	O5—S1	1.4383 (13)
C6—C1—C2	118.18 (18)	C17—C16—S1	113.76 (10)
C6—C1—H1	120.9	C15—C16—H16	108.8
C2—C1—H1	120.9	C17—C16—H16	108.8
C3—C2—C1	121.68 (18)	S1—C16—H16	108.8
C3—C2—H2	119.2	C18—C17—C16	113.82 (11)
C1—C2—H2	119.2	C18—C17—C8	114.52 (11)
C2—C3—C4	121.80 (17)	C16—C17—C8	102.29 (10)
C2—C3—H3	119.1	C18—C17—H17	108.6
C4—C3—H3	119.1	C16—C17—H17	108.6
C5—C4—C12	116.31 (16)	C8—C17—H17	108.6
C5—C4—C3	115.20 (17)	C19—C18—C17	123.55 (13)
C12—C4—C3	128.50 (16)	C19—C18—H18	118.2
C6—C5—C4	122.94 (15)	C17—C18—H18	118.2
C6—C5—C9	113.52 (13)	C18—C19—C20	121.14 (14)
C4—C5—C9	123.54 (15)	C18—C19—H19	119.4
C1—C6—C5	120.19 (15)	C20—C19—H19	119.4
C1—C6—C7	132.45 (16)	O2—C20—O3	123.92 (14)
C5—C6—C7	107.36 (13)	O2—C20—C19	125.58 (13)
O1—C7—C6	127.61 (15)	O3—C20—C19	110.49 (13)
O1—C7—C8	124.66 (14)	O3—C21—C22	111.1 (2)
C6—C7—C8	107.71 (12)	O3—C21—H21A	109.4
N1—C8—C9	112.97 (11)	C22—C21—H21A	109.4
N1—C8—C17	101.47 (11)	O3—C21—H21B	109.4
C9—C8—C17	115.83 (11)	C22—C21—H21B	109.4
N1—C8—C7	112.47 (12)	H21A—C21—H21B	108.0
C9—C8—C7	102.36 (11)	C21—C22—H22A	109.5
C17—C8—C7	112.18 (11)	C21—C22—H22B	109.5
C10—C9—C5	118.51 (14)	H22A—C22—H22B	109.5
C10—C9—C8	132.53 (14)	C21—C22—H22C	109.5
C5—C9—C8	108.93 (13)	H22A—C22—H22C	109.5
C9—C10—C11	118.95 (16)	H22B—C22—H22C	109.5
C9—C10—H10	120.5	C28—C23—C24	120.76 (17)
C11—C10—H10	120.5	C28—C23—S1	120.03 (13)
C12—C11—C10	122.53 (17)	C24—C23—S1	119.04 (13)
C12—C11—H11	118.7	C25—C24—C23	119.33 (19)
C10—C11—H11	118.7	C25—C24—H24	120.3
C11—C12—C4	120.15 (15)	C23—C24—H24	120.3
C11—C12—H12	119.9	C26—C25—C24	120.4 (2)
C4—C12—H12	119.9	C26—C25—H25	119.8
N1—C13—C14	111.99 (16)	C24—C25—H25	119.8
N1—C13—H13A	109.2	C25—C26—C27	120.3 (2)
C14—C13—H13A	109.2	C25—C26—H26	119.8
N1—C13—H13B	109.2	C27—C26—H26	119.8
C14—C13—H13B	109.2	C26—C27—C28	120.3 (2)
H13A—C13—H13B	107.9	C26—C27—H27	119.8
C13—C14—H14A	109.5	C28—C27—H27	119.8
C13—C14—H14B	109.5	C23—C28—C27	118.84 (18)
H14A—C14—H14B	109.5	C23—C28—H28	120.6
C13—C14—H14C	109.5	C27—C28—H28	120.6
H14A—C14—H14C	109.5	C13—N1—C15	113.66 (13)
H14B—C14—H14C	109.5	C13—N1—C8	114.79 (13)
N1—C15—C16	104.64 (11)	C15—N1—C8	107.01 (11)
N1—C15—H15A	110.8	C20—O3—C21	116.87 (13)
C16—C15—H15A	110.8	O4—S1—O5	118.19 (8)
N1—C15—H15B	110.8	O4—S1—C23	109.19 (8)
C16—C15—H15B	110.8	O5—S1—C23	108.26 (8)
H15A—C15—H15B	108.9	O4—S1—C16	107.00 (8)
C15—C16—C17	105.89 (11)	O5—S1—C16	109.48 (8)
C15—C16—S1	110.67 (10)	C23—S1—C16	103.78 (7)
C6—C1—C2—C3	−1.0 (3)	S1—C16—C17—C8	−142.41 (10)
C1—C2—C3—C4	0.2 (3)	N1—C8—C17—C18	162.09 (12)
C2—C3—C4—C5	0.6 (3)	C9—C8—C17—C18	−75.18 (16)
C2—C3—C4—C12	−179.67 (18)	C7—C8—C17—C18	41.83 (16)
C12—C4—C5—C6	179.53 (14)	N1—C8—C17—C16	38.46 (13)
C3—C4—C5—C6	−0.7 (2)	C9—C8—C17—C16	161.19 (12)
C12—C4—C5—C9	0.4 (2)	C7—C8—C17—C16	−81.79 (13)
C3—C4—C5—C9	−179.81 (14)	C16—C17—C18—C19	−127.00 (14)
C2—C1—C6—C5	0.9 (2)	C8—C17—C18—C19	115.79 (15)
C2—C1—C6—C7	−178.66 (15)	C17—C18—C19—C20	177.52 (12)
C4—C5—C6—C1	0.0 (2)	C18—C19—C20—O2	4.1 (2)
C9—C5—C6—C1	179.14 (13)	C18—C19—C20—O3	−174.71 (13)
C4—C5—C6—C7	179.61 (13)	C28—C23—C24—C25	−1.1 (3)
C9—C5—C6—C7	−1.21 (16)	S1—C23—C24—C25	174.11 (17)
C1—C6—C7—O1	1.0 (3)	C23—C24—C25—C26	1.0 (4)
C5—C6—C7—O1	−178.59 (14)	C24—C25—C26—C27	0.4 (4)
C1—C6—C7—C8	−177.43 (16)	C25—C26—C27—C28	−1.7 (4)
C5—C6—C7—C8	2.98 (15)	C24—C23—C28—C27	−0.1 (3)
O1—C7—C8—N1	−60.44 (18)	S1—C23—C28—C27	−175.30 (13)
C6—C7—C8—N1	118.04 (12)	C26—C27—C28—C23	1.5 (3)
O1—C7—C8—C9	178.03 (14)	C14—C13—N1—C15	68.2 (2)
C6—C7—C8—C9	−3.49 (13)	C14—C13—N1—C8	−168.20 (17)
O1—C7—C8—C17	53.20 (18)	C16—C15—N1—C13	158.39 (14)
C6—C7—C8—C17	−128.32 (12)	C16—C15—N1—C8	30.61 (17)
C6—C5—C9—C10	−179.75 (13)	C9—C8—N1—C13	64.42 (18)
C4—C5—C9—C10	−0.6 (2)	C17—C8—N1—C13	−170.90 (13)
C6—C5—C9—C8	−1.16 (16)	C7—C8—N1—C13	−50.85 (17)
C4—C5—C9—C8	178.02 (13)	C9—C8—N1—C15	−168.47 (13)
N1—C8—C9—C10	59.9 (2)	C17—C8—N1—C15	−43.79 (15)
C17—C8—C9—C10	−56.5 (2)	C7—C8—N1—C15	76.27 (15)
C7—C8—C9—C10	−178.87 (16)	O2—C20—O3—C21	−3.2 (2)
N1—C8—C9—C5	−118.37 (13)	C19—C20—O3—C21	175.66 (14)
C17—C8—C9—C5	125.19 (13)	C22—C21—O3—C20	82.8 (2)
C7—C8—C9—C5	2.81 (14)	C28—C23—S1—O4	−145.29 (14)
C5—C9—C10—C11	0.3 (2)	C24—C23—S1—O4	39.47 (16)
C8—C9—C10—C11	−177.86 (15)	C28—C23—S1—O5	−15.38 (15)
C9—C10—C11—C12	0.0 (3)	C24—C23—S1—O5	169.37 (14)
C10—C11—C12—C4	−0.2 (3)	C28—C23—S1—C16	100.88 (14)
C5—C4—C12—C11	−0.1 (2)	C24—C23—S1—C16	−74.36 (15)
C3—C4—C12—C11	−179.79 (17)	C15—C16—S1—O4	66.64 (13)
N1—C15—C16—C17	−4.79 (17)	C17—C16—S1—O4	−174.29 (10)
N1—C15—C16—S1	118.93 (12)	C15—C16—S1—O5	−62.57 (13)
C15—C16—C17—C18	−144.74 (13)	C17—C16—S1—O5	56.50 (12)
S1—C16—C17—C18	93.50 (13)	C15—C16—S1—C23	−177.97 (11)
C15—C16—C17—C8	−20.65 (15)	C17—C16—S1—C23	−58.90 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21A···O1i	0.97	2.53	3.452 (3)	160
C28—H28···O5ii	0.93	2.55	3.336 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21A⋯O1i	0.97	2.53	3.452 (3)	160
C28—H28⋯O5ii	0.93	2.55	3.336 (3)	142

Symmetry codes: (i) ; (ii) .