Ethyl 6-(6-meth-oxy-2-naphth-yl)-2-oxo-4-(2-thien-yl)cyclo-hex-3-ene-1-carboxyl-ate.

The title compound, C(24)H(22)O(4)S, was prepared by reaction between (2E)-3-(6-meth-oxy-2-naphth-yl)-1-(2-thien-yl)prop-2-en-1-one and ethyl acetoacetate. In the crystal, the cyclo-hexenone ring shows a distorted half-chair conformation. The length of the double bond in the cyclohexenone ring [1.343 (4) Å] is normal.

Related literature

For related structures, see: Fischer et al. (2007 ▶; 2008 ▶). For the use of cyclo­hexenones in organic synthesis, see: Padmavathi et al. (1999 ▶, 2001 ▶). For pharmaceutical applications of cyclo­hexenone derivatives, see: Hoye & Tennakoon (2000 ▶); Hiromichi et al. (2002 ▶).

Experimental

Crystal data

C24H22O4S

M = 406.48

Monoclinic,

a = 18.2501 (4) Å

b = 11.7176 (2) Å

c = 9.6846 (2) Å

β = 93.048 (1)°

V = 2068.10 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 296 K

0.45 × 0.29 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.922, T max = 0.972

17446 measured reflections

4035 independent reflections

2880 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.202

S = 1.02

4035 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021308/sj2629sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021308/sj2629Isup2.hkl

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

C24H22O4S	F(000) = 856
Mr = 406.48	Dx = 1.305 Mg m−3
Monoclinic, P21/c	Melting point = 415–418 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 18.2501 (4) Å	Cell parameters from 8575 reflections
b = 11.7176 (2) Å	θ = 2.3–28.1°
c = 9.6846 (2) Å	µ = 0.18 mm−1
β = 93.048 (1)°	T = 296 K
V = 2068.10 (7) Å3	Block, colourless
Z = 4	0.45 × 0.29 × 0.16 mm

Bruker SMART CCD area-detector diffractometer	4035 independent reflections
Radiation source: fine-focus sealed tube	2880 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −22→22
Tmin = 0.922, Tmax = 0.972	k = −11→14
17446 measured reflections	l = −11→10

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.095P)2 + 0.9907P] where P = (Fo2 + 2Fc2)/3
4035 reflections	(Δ/σ)max = 0.001
282 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.1379 (2)	0.5193 (3)	0.4085 (3)	0.0917 (10)
H1A	0.1524	0.4568	0.4625	0.110*
C2	0.0777 (2)	0.5795 (4)	0.4405 (4)	0.0955 (12)
H2A	0.0516	0.5577	0.5160	0.115*
C3	0.05423 (16)	0.6739 (3)	0.3619 (4)	0.0845 (9)
C4	0.09205 (15)	0.7057 (3)	0.2525 (3)	0.0733 (8)
H4A	0.0762	0.7682	0.1997	0.088*
C5	0.15546 (13)	0.6457 (2)	0.2168 (3)	0.0593 (6)
C6	0.17879 (16)	0.5499 (2)	0.2952 (3)	0.0661 (7)
C7	0.24126 (19)	0.4896 (3)	0.2584 (3)	0.0810 (9)
H7A	0.2567	0.4267	0.3108	0.097*
C8	0.28020 (16)	0.5208 (3)	0.1474 (3)	0.0787 (9)
C9	0.25672 (16)	0.6164 (3)	0.0705 (3)	0.0768 (8)
H9A	0.2829	0.6392	−0.0045	0.092*
C10	0.19634 (15)	0.6766 (3)	0.1033 (3)	0.0694 (7)
H10A	0.1818	0.7393	0.0497	0.083*
C11A	0.3387 (4)	0.4303 (7)	0.1361 (8)	0.0567 (17)	0.489 (11)
H11A	0.3274	0.3649	0.1944	0.068*	0.489 (11)
C11B	0.3537 (3)	0.4735 (6)	0.0866 (7)	0.0498 (15)	0.511 (11)
H11B	0.3642	0.5140	0.0013	0.060*	0.511 (11)
C12	0.41517 (14)	0.4837 (2)	0.1877 (3)	0.0587 (6)
H12A	0.4212	0.5568	0.1426	0.070*
H12B	0.4149	0.4974	0.2864	0.070*
C13	0.47940 (14)	0.4085 (2)	0.1587 (3)	0.0563 (6)
C14	0.47374 (16)	0.3283 (2)	0.0596 (3)	0.0654 (7)
H14A	0.5156	0.2875	0.0396	0.078*
C15	0.40620 (18)	0.3025 (3)	−0.0168 (3)	0.0779 (8)
C16A	0.3403 (3)	0.3921 (6)	−0.0137 (8)	0.0659 (19)	0.511 (11)
H16A	0.3472	0.4565	−0.0763	0.079*	0.511 (11)
C16B	0.3388 (3)	0.3456 (5)	0.0561 (7)	0.0501 (17)	0.489 (11)
H16B	0.3323	0.3031	0.1418	0.060*	0.489 (11)
C17	0.27068 (18)	0.3302 (3)	−0.0483 (4)	0.0771 (8)
C18	0.1848 (5)	0.3678 (7)	−0.2222 (6)	0.190 (3)
H18A	0.1700	0.2910	−0.1987	0.228*
H18B	0.1906	0.3710	−0.3211	0.228*
C19	0.1297 (5)	0.4479 (7)	−0.1848 (8)	0.212 (3)
H19A	0.0839	0.4294	−0.2329	0.317*
H19B	0.1442	0.5236	−0.2095	0.317*
H19C	0.1240	0.4443	−0.0869	0.317*
C20	0.54589 (14)	0.4261 (2)	0.2453 (3)	0.0628 (7)
C21	0.56318 (14)	0.5200 (2)	0.3318 (3)	0.0689 (7)
H21A	0.5331	0.5831	0.3424	0.083*
C22	0.63359 (19)	0.5044 (3)	0.4008 (4)	0.0956 (10)
H22A	0.6556	0.5588	0.4595	0.115*
C23	0.66455 (19)	0.4056 (3)	0.3736 (5)	0.1036 (12)
H23A	0.7098	0.3828	0.4128	0.124*
C24	−0.0321 (3)	0.8260 (6)	0.3341 (8)	0.169 (3)
H24A	−0.0767	0.8524	0.3713	0.254*
H24B	−0.0408	0.8082	0.2379	0.254*
H24C	0.0047	0.8844	0.3443	0.254*
S1	0.61390 (5)	0.32512 (7)	0.26068 (12)	0.0945 (4)
O1	0.2523 (2)	0.3953 (3)	−0.1501 (3)	0.1250 (10)
O2	0.23644 (17)	0.2511 (2)	−0.0137 (3)	0.1130 (9)
O3	−0.00726 (14)	0.7259 (3)	0.4069 (3)	0.1238 (11)
O4	0.40154 (14)	0.2313 (2)	−0.1083 (2)	0.0996 (8)

	U11	U22	U33	U12	U13	U23
C1	0.127 (3)	0.076 (2)	0.070 (2)	−0.028 (2)	−0.0062 (19)	0.0070 (16)
C2	0.106 (3)	0.110 (3)	0.071 (2)	−0.048 (2)	0.0134 (18)	−0.006 (2)
C3	0.0610 (16)	0.109 (3)	0.084 (2)	−0.0190 (16)	0.0062 (14)	−0.015 (2)
C4	0.0597 (15)	0.080 (2)	0.0794 (18)	0.0007 (13)	−0.0029 (13)	−0.0023 (15)
C5	0.0576 (13)	0.0555 (15)	0.0637 (14)	−0.0041 (11)	−0.0067 (11)	−0.0018 (12)
C6	0.0832 (17)	0.0517 (15)	0.0614 (15)	−0.0115 (13)	−0.0138 (13)	−0.0029 (12)
C7	0.104 (2)	0.0579 (17)	0.077 (2)	0.0198 (16)	−0.0339 (17)	−0.0135 (15)
C8	0.0733 (17)	0.079 (2)	0.080 (2)	0.0214 (15)	−0.0240 (15)	−0.0337 (17)
C9	0.0673 (16)	0.085 (2)	0.0781 (18)	0.0060 (15)	0.0041 (14)	−0.0083 (16)
C10	0.0680 (16)	0.0662 (18)	0.0738 (17)	0.0069 (13)	0.0020 (13)	0.0082 (14)
C11A	0.067 (3)	0.047 (4)	0.056 (4)	−0.003 (3)	0.002 (3)	0.006 (3)
C11B	0.062 (3)	0.037 (3)	0.050 (3)	0.001 (2)	0.003 (2)	0.005 (2)
C12	0.0691 (14)	0.0452 (13)	0.0620 (14)	0.0002 (11)	0.0051 (11)	−0.0005 (11)
C13	0.0683 (14)	0.0429 (13)	0.0588 (14)	0.0007 (10)	0.0134 (11)	0.0065 (11)
C14	0.0757 (16)	0.0535 (15)	0.0682 (16)	0.0077 (12)	0.0151 (13)	−0.0001 (13)
C15	0.089 (2)	0.0624 (17)	0.0824 (19)	0.0045 (15)	0.0099 (15)	−0.0215 (16)
C16A	0.085 (4)	0.052 (4)	0.061 (4)	−0.002 (3)	0.003 (3)	0.002 (3)
C16B	0.068 (3)	0.037 (3)	0.045 (3)	−0.002 (2)	0.001 (2)	0.001 (3)
C17	0.0830 (19)	0.0625 (19)	0.086 (2)	−0.0068 (15)	0.0024 (16)	−0.0232 (17)
C18	0.266 (8)	0.195 (6)	0.103 (4)	0.108 (6)	−0.067 (5)	−0.030 (4)
C19	0.222 (8)	0.195 (7)	0.209 (7)	0.017 (7)	−0.066 (6)	−0.024 (6)
C20	0.0628 (14)	0.0547 (15)	0.0719 (16)	0.0001 (11)	0.0139 (12)	0.0094 (13)
C21	0.0631 (14)	0.0668 (17)	0.0753 (17)	0.0019 (12)	−0.0092 (12)	−0.0095 (14)
C22	0.084 (2)	0.090 (2)	0.110 (3)	−0.0001 (19)	−0.0164 (19)	−0.011 (2)
C23	0.0742 (19)	0.091 (3)	0.144 (3)	−0.0013 (18)	−0.015 (2)	0.014 (2)
C24	0.101 (3)	0.190 (6)	0.220 (6)	0.053 (4)	0.038 (4)	−0.022 (5)
S1	0.0799 (5)	0.0638 (5)	0.1391 (9)	0.0073 (4)	−0.0014 (5)	0.0047 (5)
O1	0.171 (3)	0.105 (2)	0.100 (2)	0.004 (2)	0.022 (2)	0.0166 (17)
O2	0.140 (2)	0.0862 (18)	0.1104 (19)	−0.0330 (17)	−0.0168 (17)	0.0061 (15)
O3	0.0724 (15)	0.181 (3)	0.120 (2)	−0.0047 (18)	0.0278 (15)	−0.032 (2)
O4	0.1168 (18)	0.0868 (16)	0.0945 (16)	0.0164 (13)	−0.0023 (13)	−0.0425 (14)

C1—C2	1.354 (5)	C14—C15	1.436 (4)
C1—C6	1.406 (4)	C14—H14A	0.9300
C1—H1A	0.9300	C15—O4	1.217 (3)
C2—C3	1.396 (5)	C15—C16B	1.536 (6)
C2—H2A	0.9300	C15—C16A	1.599 (7)
C3—C4	1.347 (4)	C16A—C17	1.486 (7)
C3—O3	1.369 (4)	C16A—H16A	0.9800
C4—C5	1.413 (4)	C16B—C17	1.571 (6)
C4—H4A	0.9300	C16B—H16B	0.9800
C5—C10	1.408 (4)	C17—O2	1.176 (4)
C5—C6	1.409 (4)	C17—O1	1.277 (4)
C6—C7	1.403 (4)	C18—O1	1.420 (7)
C7—C8	1.370 (5)	C18—C19	1.437 (9)
C7—H7A	0.9300	C18—H18A	0.9700
C8—C9	1.400 (5)	C18—H18B	0.9700
C8—C11A	1.513 (7)	C19—H19A	0.9600
C8—C11B	1.593 (6)	C19—H19B	0.9600
C9—C10	1.360 (4)	C19—H19C	0.9600
C9—H9A	0.9300	C20—C21	1.409 (4)
C10—H10A	0.9300	C20—S1	1.715 (3)
C11A—C16A	1.520 (8)	C21—C22	1.428 (4)
C11A—C12	1.586 (7)	C21—H21A	0.9300
C11A—H11A	0.9800	C22—C23	1.321 (5)
C11B—C12	1.455 (6)	C22—H22A	0.9300
C11B—C16B	1.549 (7)	C23—S1	1.683 (4)
C11B—H11B	0.9800	C23—H23A	0.9300
C12—C13	1.505 (3)	C24—O3	1.429 (7)
C12—H12A	0.9700	C24—H24A	0.9600
C12—H12B	0.9700	C24—H24B	0.9600
C13—C14	1.343 (4)	C24—H24C	0.9600
C13—C20	1.453 (4)
C2—C1—C6	121.1 (3)	C13—C14—H14A	118.4
C2—C1—H1A	119.5	C15—C14—H14A	118.4
C6—C1—H1A	119.5	O4—C15—C14	123.0 (3)
C1—C2—C3	121.1 (3)	O4—C15—C16B	122.3 (3)
C1—C2—H2A	119.4	C14—C15—C16B	112.3 (3)
C3—C2—H2A	119.4	O4—C15—C16A	116.1 (3)
C4—C3—O3	126.1 (4)	C14—C15—C16A	118.6 (3)
C4—C3—C2	119.5 (3)	C16B—C15—C16A	32.2 (2)
O3—C3—C2	114.4 (3)	C17—C16A—C11A	107.4 (5)
C3—C4—C5	121.0 (3)	C17—C16A—C15	108.1 (4)
C3—C4—H4A	119.5	C11A—C16A—C15	105.3 (5)
C5—C4—H4A	119.5	C17—C16A—H16A	111.9
C10—C5—C6	117.9 (2)	C11A—C16A—H16A	111.9
C10—C5—C4	122.6 (3)	C15—C16A—H16A	111.9
C6—C5—C4	119.5 (3)	C15—C16B—C11B	105.6 (4)
C7—C6—C1	122.8 (3)	C15—C16B—C17	107.0 (4)
C7—C6—C5	119.4 (3)	C11B—C16B—C17	111.0 (4)
C1—C6—C5	117.8 (3)	C15—C16B—H16B	111.0
C8—C7—C6	121.8 (3)	C11B—C16B—H16B	111.0
C8—C7—H7A	119.1	C17—C16B—H16B	111.0
C6—C7—H7A	119.1	O2—C17—O1	124.7 (3)
C7—C8—C9	118.3 (3)	O2—C17—C16A	141.4 (5)
C7—C8—C11A	105.5 (5)	O1—C17—C16A	93.9 (5)
C9—C8—C11A	136.0 (5)	O2—C17—C16B	108.7 (4)
C7—C8—C11B	132.8 (4)	O1—C17—C16B	126.5 (4)
C9—C8—C11B	108.8 (4)	C16A—C17—C16B	32.9 (3)
C11A—C8—C11B	28.1 (2)	O1—C18—C19	109.2 (5)
C10—C9—C8	121.3 (3)	O1—C18—H18A	109.8
C10—C9—H9A	119.3	C19—C18—H18A	109.8
C8—C9—H9A	119.3	O1—C18—H18B	109.8
C9—C10—C5	121.2 (3)	C19—C18—H18B	109.8
C9—C10—H10A	119.4	H18A—C18—H18B	108.3
C5—C10—H10A	119.4	C18—C19—H19A	109.5
C8—C11A—C16A	108.9 (5)	C18—C19—H19B	109.5
C8—C11A—C12	108.2 (5)	H19A—C19—H19B	109.5
C16A—C11A—C12	110.9 (5)	C18—C19—H19C	109.5
C8—C11A—H11A	109.6	H19A—C19—H19C	109.5
C16A—C11A—H11A	109.6	H19B—C19—H19C	109.5
C12—C11A—H11A	109.6	C21—C20—C13	127.4 (2)
C12—C11B—C16B	109.2 (4)	C21—C20—S1	110.4 (2)
C12—C11B—C8	110.9 (4)	C13—C20—S1	122.1 (2)
C16B—C11B—C8	105.4 (5)	C20—C21—C22	110.3 (3)
C12—C11B—H11B	110.4	C20—C21—H21A	124.9
C16B—C11B—H11B	110.4	C22—C21—H21A	124.9
C8—C11B—H11B	110.4	C23—C22—C21	113.7 (3)
C11B—C12—C13	114.0 (3)	C23—C22—H22A	123.2
C11B—C12—C11A	28.5 (2)	C21—C22—H22A	123.2
C13—C12—C11A	113.0 (3)	C22—C23—S1	113.3 (3)
C11B—C12—H12A	82.6	C22—C23—H23A	123.4
C13—C12—H12A	109.0	S1—C23—H23A	123.4
C11A—C12—H12A	109.0	O3—C24—H24A	109.5
C11B—C12—H12B	129.3	O3—C24—H24B	109.5
C13—C12—H12B	109.0	H24A—C24—H24B	109.5
C11A—C12—H12B	109.0	O3—C24—H24C	109.5
H12A—C12—H12B	107.8	H24A—C24—H24C	109.5
C14—C13—C20	122.8 (2)	H24B—C24—H24C	109.5
C14—C13—C12	120.8 (2)	C23—S1—C20	92.28 (17)
C20—C13—C12	116.4 (2)	C17—O1—C18	115.4 (4)
C13—C14—C15	123.2 (3)	C3—O3—C24	116.9 (3)
C6—C1—C2—C3	0.1 (5)	C13—C14—C15—C16B	−18.7 (5)
C1—C2—C3—C4	−0.1 (5)	C13—C14—C15—C16A	16.4 (6)
C1—C2—C3—O3	−180.0 (3)	C8—C11A—C16A—C17	−68.1 (6)
O3—C3—C4—C5	179.3 (3)	C12—C11A—C16A—C17	172.9 (6)
C2—C3—C4—C5	−0.5 (5)	C8—C11A—C16A—C15	176.9 (6)
C3—C4—C5—C10	−180.0 (3)	C12—C11A—C16A—C15	57.9 (6)
C3—C4—C5—C6	1.1 (4)	O4—C15—C16A—C17	39.2 (7)
C2—C1—C6—C7	−179.8 (3)	C14—C15—C16A—C17	−157.4 (4)
C2—C1—C6—C5	0.5 (4)	C16B—C15—C16A—C17	−70.5 (7)
C10—C5—C6—C7	0.3 (4)	O4—C15—C16A—C11A	153.7 (4)
C4—C5—C6—C7	179.2 (2)	C14—C15—C16A—C11A	−42.9 (6)
C10—C5—C6—C1	179.9 (3)	C16B—C15—C16A—C11A	44.1 (5)
C4—C5—C6—C1	−1.1 (4)	O4—C15—C16B—C11B	−144.5 (4)
C1—C6—C7—C8	179.9 (3)	C14—C15—C16B—C11B	52.6 (5)
C5—C6—C7—C8	−0.4 (4)	C16A—C15—C16B—C11B	−55.9 (5)
C6—C7—C8—C9	0.7 (4)	O4—C15—C16B—C17	−26.2 (7)
C6—C7—C8—C11A	−175.6 (3)	C14—C15—C16B—C17	170.9 (3)
C6—C7—C8—C11B	176.6 (3)	C16A—C15—C16B—C17	62.4 (6)
C7—C8—C9—C10	−0.7 (4)	C12—C11B—C16B—C15	−66.7 (5)
C11A—C8—C9—C10	174.1 (4)	C8—C11B—C16B—C15	174.1 (5)
C11B—C8—C9—C10	−177.6 (3)	C12—C11B—C16B—C17	177.7 (5)
C8—C9—C10—C5	0.6 (5)	C8—C11B—C16B—C17	58.5 (5)
C6—C5—C10—C9	−0.4 (4)	C11A—C16A—C17—O2	−58.3 (7)
C4—C5—C10—C9	−179.3 (3)	C15—C16A—C17—O2	54.8 (8)
C7—C8—C11A—C16A	132.9 (5)	C11A—C16A—C17—O1	123.3 (5)
C9—C8—C11A—C16A	−42.3 (8)	C15—C16A—C17—O1	−123.5 (5)
C11B—C8—C11A—C16A	−59.2 (7)	C11A—C16A—C17—C16B	−48.7 (5)
C7—C8—C11A—C12	−106.5 (5)	C15—C16A—C17—C16B	64.4 (6)
C9—C8—C11A—C12	78.3 (6)	C15—C16B—C17—O2	104.7 (5)
C11B—C8—C11A—C12	61.4 (7)	C11B—C16B—C17—O2	−140.6 (4)
C7—C8—C11B—C12	−60.7 (7)	C15—C16B—C17—O1	−78.9 (5)
C9—C8—C11B—C12	115.5 (5)	C11B—C16B—C17—O1	35.9 (6)
C11A—C8—C11B—C12	−76.8 (8)	C15—C16B—C17—C16A	−69.0 (6)
C7—C8—C11B—C16B	57.3 (5)	C11B—C16B—C17—C16A	45.8 (5)
C9—C8—C11B—C16B	−126.5 (4)	C14—C13—C20—C21	166.3 (3)
C11A—C8—C11B—C16B	41.2 (6)	C12—C13—C20—C21	−15.2 (4)
C16B—C11B—C12—C13	45.4 (6)	C14—C13—C20—S1	−17.2 (3)
C8—C11B—C12—C13	161.1 (4)	C12—C13—C20—S1	161.28 (18)
C16B—C11B—C12—C11A	−49.0 (6)	C13—C20—C21—C22	179.4 (3)
C8—C11B—C12—C11A	66.7 (8)	S1—C20—C21—C22	2.6 (3)
C8—C11A—C12—C11B	−71.9 (8)	C20—C21—C22—C23	−2.8 (5)
C16A—C11A—C12—C11B	47.5 (6)	C21—C22—C23—S1	1.7 (5)
C8—C11A—C12—C13	−170.2 (4)	C22—C23—S1—C20	−0.1 (3)
C16A—C11A—C12—C13	−50.8 (6)	C21—C20—S1—C23	−1.5 (2)
C11B—C12—C13—C14	−9.4 (5)	C13—C20—S1—C23	−178.5 (2)
C11A—C12—C13—C14	21.7 (5)	O2—C17—O1—C18	0.9 (6)
C11B—C12—C13—C20	172.1 (4)	C16A—C17—O1—C18	179.6 (4)
C11A—C12—C13—C20	−156.9 (4)	C16B—C17—O1—C18	−175.0 (4)
C20—C13—C14—C15	173.4 (3)	C19—C18—O1—C17	104.5 (7)
C12—C13—C14—C15	−5.0 (4)	C4—C3—O3—C24	−2.5 (6)
C13—C14—C15—O4	178.6 (3)	C2—C3—O3—C24	177.4 (4)