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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1533.
Published online 2009 June 10. doi:  10.1107/S1600536809021308
PMCID: PMC2969391

Ethyl 6-(6-meth­oxy-2-naphth­yl)-2-oxo-4-(2-thien­yl)cyclo­hex-3-ene-1-carboxyl­ate

Abstract

The title compound, C24H22O4S, was prepared by reaction between (2E)-3-(6-meth­oxy-2-naphth­yl)-1-(2-thien­yl)prop-2-en-1-one and ethyl acetoacetate. In the crystal, the cyclo­hexenone 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. (2007a [triangle],b [triangle]; 2008a [triangle],b [triangle]). For the use of cyclo­hexenones in organic synthesis, see: Padmavathi et al. (1999 [triangle], 2001 [triangle]). For pharmaceutical applications of cyclo­hexenone derivatives, see: Hoye & Tennakoon (2000 [triangle]); Hiromichi et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1533-scheme1.jpg

Experimental

Crystal data

  • C24H22O4S
  • M r = 406.48
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1533-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2001 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

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

Acknowledgments

ANM thanks the University of Mysore for research facilities.

supplementary crystallographic information

Comment

Cyclohexenones are efficient synthons in building spiro compounds (Padmavathi et al., 2001) or intermediates in the synthesis of benzisoxazole or carbazole derivatives (Padmavathi et al., 1999). Cyclohexenone derivatives are well known lead compounds for the treatment of inflammation and autoimmune diseases (Hoye & Tennakoon, 2000; Hiromichi et al., 2002).

The crystal structures of a series of ethyl 6-substituted 2-oxocyclohex- 3-ene-1-carboxylates have been reported (Fischer et al., 2007; 2007a,b; 2008ab). In view of the importance of these derivatives and continuing our efforts in this field, the title compound, ethyl 6-(6- methoxynaphthalen-2-yl)-2-oxo-4-(2-thienyl)cyclohexa-3-ene-1- carboxylate, was synthesized and its crystal structure is reported in this paper.

Experimental

(2E)-3-(6-methoxy-2-naphthyl)-1-(2-thienyl)prop-2-en-1-one (1.51 g, 5 mmol) and ethyl acetoacetate (0.65 g, 5 mmol) were refluxed for 6 hr in 10–15 ml of ethanol in the presence of 0.8 ml 10% NaOH. The reaction mixture was cooled to room temperature and the resulting product was filtered and recrystallized from acetonitrile (m.p.: 415–418 K). Analysis % found (calculated): C, 71.19 (71.27); H, 4.94 (4.98); S, 7.89 (7.93).

Refinement

All H atoms were placed in idealized locations (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate, but not to tip, to best fit the electron density. The large difference between min and max Uiso values for the H atoms is a result of unresolved disorder in the ethyl side chain.

Figures

Fig. 1.
A view of the crystal structure of the title compound.

Crystal data

C24H22O4SF(000) = 856
Mr = 406.48Dx = 1.305 Mg m3
Monoclinic, P21/cMelting point = 415–418 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 18.2501 (4) ÅCell parameters from 8575 reflections
b = 11.7176 (2) Åθ = 2.3–28.1°
c = 9.6846 (2) ŵ = 0.18 mm1
β = 93.048 (1)°T = 296 K
V = 2068.10 (7) Å3Block, colourless
Z = 40.45 × 0.29 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer4035 independent reflections
Radiation source: fine-focus sealed tube2880 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −22→22
Tmin = 0.922, Tmax = 0.972k = −11→14
17446 measured reflectionsl = −11→10

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.095P)2 + 0.9907P] where P = (Fo2 + 2Fc2)/3
4035 reflections(Δ/σ)max = 0.001
282 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = −0.37 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
C10.1379 (2)0.5193 (3)0.4085 (3)0.0917 (10)
H1A0.15240.45680.46250.110*
C20.0777 (2)0.5795 (4)0.4405 (4)0.0955 (12)
H2A0.05160.55770.51600.115*
C30.05423 (16)0.6739 (3)0.3619 (4)0.0845 (9)
C40.09205 (15)0.7057 (3)0.2525 (3)0.0733 (8)
H4A0.07620.76820.19970.088*
C50.15546 (13)0.6457 (2)0.2168 (3)0.0593 (6)
C60.17879 (16)0.5499 (2)0.2952 (3)0.0661 (7)
C70.24126 (19)0.4896 (3)0.2584 (3)0.0810 (9)
H7A0.25670.42670.31080.097*
C80.28020 (16)0.5208 (3)0.1474 (3)0.0787 (9)
C90.25672 (16)0.6164 (3)0.0705 (3)0.0768 (8)
H9A0.28290.6392−0.00450.092*
C100.19634 (15)0.6766 (3)0.1033 (3)0.0694 (7)
H10A0.18180.73930.04970.083*
C11A0.3387 (4)0.4303 (7)0.1361 (8)0.0567 (17)0.489 (11)
H11A0.32740.36490.19440.068*0.489 (11)
C11B0.3537 (3)0.4735 (6)0.0866 (7)0.0498 (15)0.511 (11)
H11B0.36420.51400.00130.060*0.511 (11)
C120.41517 (14)0.4837 (2)0.1877 (3)0.0587 (6)
H12A0.42120.55680.14260.070*
H12B0.41490.49740.28640.070*
C130.47940 (14)0.4085 (2)0.1587 (3)0.0563 (6)
C140.47374 (16)0.3283 (2)0.0596 (3)0.0654 (7)
H14A0.51560.28750.03960.078*
C150.40620 (18)0.3025 (3)−0.0168 (3)0.0779 (8)
C16A0.3403 (3)0.3921 (6)−0.0137 (8)0.0659 (19)0.511 (11)
H16A0.34720.4565−0.07630.079*0.511 (11)
C16B0.3388 (3)0.3456 (5)0.0561 (7)0.0501 (17)0.489 (11)
H16B0.33230.30310.14180.060*0.489 (11)
C170.27068 (18)0.3302 (3)−0.0483 (4)0.0771 (8)
C180.1848 (5)0.3678 (7)−0.2222 (6)0.190 (3)
H18A0.17000.2910−0.19870.228*
H18B0.19060.3710−0.32110.228*
C190.1297 (5)0.4479 (7)−0.1848 (8)0.212 (3)
H19A0.08390.4294−0.23290.317*
H19B0.14420.5236−0.20950.317*
H19C0.12400.4443−0.08690.317*
C200.54589 (14)0.4261 (2)0.2453 (3)0.0628 (7)
C210.56318 (14)0.5200 (2)0.3318 (3)0.0689 (7)
H21A0.53310.58310.34240.083*
C220.63359 (19)0.5044 (3)0.4008 (4)0.0956 (10)
H22A0.65560.55880.45950.115*
C230.66455 (19)0.4056 (3)0.3736 (5)0.1036 (12)
H23A0.70980.38280.41280.124*
C24−0.0321 (3)0.8260 (6)0.3341 (8)0.169 (3)
H24A−0.07670.85240.37130.254*
H24B−0.04080.80820.23790.254*
H24C0.00470.88440.34430.254*
S10.61390 (5)0.32512 (7)0.26068 (12)0.0945 (4)
O10.2523 (2)0.3953 (3)−0.1501 (3)0.1250 (10)
O20.23644 (17)0.2511 (2)−0.0137 (3)0.1130 (9)
O3−0.00726 (14)0.7259 (3)0.4069 (3)0.1238 (11)
O40.40154 (14)0.2313 (2)−0.1083 (2)0.0996 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.127 (3)0.076 (2)0.070 (2)−0.028 (2)−0.0062 (19)0.0070 (16)
C20.106 (3)0.110 (3)0.071 (2)−0.048 (2)0.0134 (18)−0.006 (2)
C30.0610 (16)0.109 (3)0.084 (2)−0.0190 (16)0.0062 (14)−0.015 (2)
C40.0597 (15)0.080 (2)0.0794 (18)0.0007 (13)−0.0029 (13)−0.0023 (15)
C50.0576 (13)0.0555 (15)0.0637 (14)−0.0041 (11)−0.0067 (11)−0.0018 (12)
C60.0832 (17)0.0517 (15)0.0614 (15)−0.0115 (13)−0.0138 (13)−0.0029 (12)
C70.104 (2)0.0579 (17)0.077 (2)0.0198 (16)−0.0339 (17)−0.0135 (15)
C80.0733 (17)0.079 (2)0.080 (2)0.0214 (15)−0.0240 (15)−0.0337 (17)
C90.0673 (16)0.085 (2)0.0781 (18)0.0060 (15)0.0041 (14)−0.0083 (16)
C100.0680 (16)0.0662 (18)0.0738 (17)0.0069 (13)0.0020 (13)0.0082 (14)
C11A0.067 (3)0.047 (4)0.056 (4)−0.003 (3)0.002 (3)0.006 (3)
C11B0.062 (3)0.037 (3)0.050 (3)0.001 (2)0.003 (2)0.005 (2)
C120.0691 (14)0.0452 (13)0.0620 (14)0.0002 (11)0.0051 (11)−0.0005 (11)
C130.0683 (14)0.0429 (13)0.0588 (14)0.0007 (10)0.0134 (11)0.0065 (11)
C140.0757 (16)0.0535 (15)0.0682 (16)0.0077 (12)0.0151 (13)−0.0001 (13)
C150.089 (2)0.0624 (17)0.0824 (19)0.0045 (15)0.0099 (15)−0.0215 (16)
C16A0.085 (4)0.052 (4)0.061 (4)−0.002 (3)0.003 (3)0.002 (3)
C16B0.068 (3)0.037 (3)0.045 (3)−0.002 (2)0.001 (2)0.001 (3)
C170.0830 (19)0.0625 (19)0.086 (2)−0.0068 (15)0.0024 (16)−0.0232 (17)
C180.266 (8)0.195 (6)0.103 (4)0.108 (6)−0.067 (5)−0.030 (4)
C190.222 (8)0.195 (7)0.209 (7)0.017 (7)−0.066 (6)−0.024 (6)
C200.0628 (14)0.0547 (15)0.0719 (16)0.0001 (11)0.0139 (12)0.0094 (13)
C210.0631 (14)0.0668 (17)0.0753 (17)0.0019 (12)−0.0092 (12)−0.0095 (14)
C220.084 (2)0.090 (2)0.110 (3)−0.0001 (19)−0.0164 (19)−0.011 (2)
C230.0742 (19)0.091 (3)0.144 (3)−0.0013 (18)−0.015 (2)0.014 (2)
C240.101 (3)0.190 (6)0.220 (6)0.053 (4)0.038 (4)−0.022 (5)
S10.0799 (5)0.0638 (5)0.1391 (9)0.0073 (4)−0.0014 (5)0.0047 (5)
O10.171 (3)0.105 (2)0.100 (2)0.004 (2)0.022 (2)0.0166 (17)
O20.140 (2)0.0862 (18)0.1104 (19)−0.0330 (17)−0.0168 (17)0.0061 (15)
O30.0724 (15)0.181 (3)0.120 (2)−0.0047 (18)0.0278 (15)−0.032 (2)
O40.1168 (18)0.0868 (16)0.0945 (16)0.0164 (13)−0.0023 (13)−0.0425 (14)

Geometric parameters (Å, °)

C1—C21.354 (5)C14—C151.436 (4)
C1—C61.406 (4)C14—H14A0.9300
C1—H1A0.9300C15—O41.217 (3)
C2—C31.396 (5)C15—C16B1.536 (6)
C2—H2A0.9300C15—C16A1.599 (7)
C3—C41.347 (4)C16A—C171.486 (7)
C3—O31.369 (4)C16A—H16A0.9800
C4—C51.413 (4)C16B—C171.571 (6)
C4—H4A0.9300C16B—H16B0.9800
C5—C101.408 (4)C17—O21.176 (4)
C5—C61.409 (4)C17—O11.277 (4)
C6—C71.403 (4)C18—O11.420 (7)
C7—C81.370 (5)C18—C191.437 (9)
C7—H7A0.9300C18—H18A0.9700
C8—C91.400 (5)C18—H18B0.9700
C8—C11A1.513 (7)C19—H19A0.9600
C8—C11B1.593 (6)C19—H19B0.9600
C9—C101.360 (4)C19—H19C0.9600
C9—H9A0.9300C20—C211.409 (4)
C10—H10A0.9300C20—S11.715 (3)
C11A—C16A1.520 (8)C21—C221.428 (4)
C11A—C121.586 (7)C21—H21A0.9300
C11A—H11A0.9800C22—C231.321 (5)
C11B—C121.455 (6)C22—H22A0.9300
C11B—C16B1.549 (7)C23—S11.683 (4)
C11B—H11B0.9800C23—H23A0.9300
C12—C131.505 (3)C24—O31.429 (7)
C12—H12A0.9700C24—H24A0.9600
C12—H12B0.9700C24—H24B0.9600
C13—C141.343 (4)C24—H24C0.9600
C13—C201.453 (4)
C2—C1—C6121.1 (3)C13—C14—H14A118.4
C2—C1—H1A119.5C15—C14—H14A118.4
C6—C1—H1A119.5O4—C15—C14123.0 (3)
C1—C2—C3121.1 (3)O4—C15—C16B122.3 (3)
C1—C2—H2A119.4C14—C15—C16B112.3 (3)
C3—C2—H2A119.4O4—C15—C16A116.1 (3)
C4—C3—O3126.1 (4)C14—C15—C16A118.6 (3)
C4—C3—C2119.5 (3)C16B—C15—C16A32.2 (2)
O3—C3—C2114.4 (3)C17—C16A—C11A107.4 (5)
C3—C4—C5121.0 (3)C17—C16A—C15108.1 (4)
C3—C4—H4A119.5C11A—C16A—C15105.3 (5)
C5—C4—H4A119.5C17—C16A—H16A111.9
C10—C5—C6117.9 (2)C11A—C16A—H16A111.9
C10—C5—C4122.6 (3)C15—C16A—H16A111.9
C6—C5—C4119.5 (3)C15—C16B—C11B105.6 (4)
C7—C6—C1122.8 (3)C15—C16B—C17107.0 (4)
C7—C6—C5119.4 (3)C11B—C16B—C17111.0 (4)
C1—C6—C5117.8 (3)C15—C16B—H16B111.0
C8—C7—C6121.8 (3)C11B—C16B—H16B111.0
C8—C7—H7A119.1C17—C16B—H16B111.0
C6—C7—H7A119.1O2—C17—O1124.7 (3)
C7—C8—C9118.3 (3)O2—C17—C16A141.4 (5)
C7—C8—C11A105.5 (5)O1—C17—C16A93.9 (5)
C9—C8—C11A136.0 (5)O2—C17—C16B108.7 (4)
C7—C8—C11B132.8 (4)O1—C17—C16B126.5 (4)
C9—C8—C11B108.8 (4)C16A—C17—C16B32.9 (3)
C11A—C8—C11B28.1 (2)O1—C18—C19109.2 (5)
C10—C9—C8121.3 (3)O1—C18—H18A109.8
C10—C9—H9A119.3C19—C18—H18A109.8
C8—C9—H9A119.3O1—C18—H18B109.8
C9—C10—C5121.2 (3)C19—C18—H18B109.8
C9—C10—H10A119.4H18A—C18—H18B108.3
C5—C10—H10A119.4C18—C19—H19A109.5
C8—C11A—C16A108.9 (5)C18—C19—H19B109.5
C8—C11A—C12108.2 (5)H19A—C19—H19B109.5
C16A—C11A—C12110.9 (5)C18—C19—H19C109.5
C8—C11A—H11A109.6H19A—C19—H19C109.5
C16A—C11A—H11A109.6H19B—C19—H19C109.5
C12—C11A—H11A109.6C21—C20—C13127.4 (2)
C12—C11B—C16B109.2 (4)C21—C20—S1110.4 (2)
C12—C11B—C8110.9 (4)C13—C20—S1122.1 (2)
C16B—C11B—C8105.4 (5)C20—C21—C22110.3 (3)
C12—C11B—H11B110.4C20—C21—H21A124.9
C16B—C11B—H11B110.4C22—C21—H21A124.9
C8—C11B—H11B110.4C23—C22—C21113.7 (3)
C11B—C12—C13114.0 (3)C23—C22—H22A123.2
C11B—C12—C11A28.5 (2)C21—C22—H22A123.2
C13—C12—C11A113.0 (3)C22—C23—S1113.3 (3)
C11B—C12—H12A82.6C22—C23—H23A123.4
C13—C12—H12A109.0S1—C23—H23A123.4
C11A—C12—H12A109.0O3—C24—H24A109.5
C11B—C12—H12B129.3O3—C24—H24B109.5
C13—C12—H12B109.0H24A—C24—H24B109.5
C11A—C12—H12B109.0O3—C24—H24C109.5
H12A—C12—H12B107.8H24A—C24—H24C109.5
C14—C13—C20122.8 (2)H24B—C24—H24C109.5
C14—C13—C12120.8 (2)C23—S1—C2092.28 (17)
C20—C13—C12116.4 (2)C17—O1—C18115.4 (4)
C13—C14—C15123.2 (3)C3—O3—C24116.9 (3)
C6—C1—C2—C30.1 (5)C13—C14—C15—C16B−18.7 (5)
C1—C2—C3—C4−0.1 (5)C13—C14—C15—C16A16.4 (6)
C1—C2—C3—O3−180.0 (3)C8—C11A—C16A—C17−68.1 (6)
O3—C3—C4—C5179.3 (3)C12—C11A—C16A—C17172.9 (6)
C2—C3—C4—C5−0.5 (5)C8—C11A—C16A—C15176.9 (6)
C3—C4—C5—C10−180.0 (3)C12—C11A—C16A—C1557.9 (6)
C3—C4—C5—C61.1 (4)O4—C15—C16A—C1739.2 (7)
C2—C1—C6—C7−179.8 (3)C14—C15—C16A—C17−157.4 (4)
C2—C1—C6—C50.5 (4)C16B—C15—C16A—C17−70.5 (7)
C10—C5—C6—C70.3 (4)O4—C15—C16A—C11A153.7 (4)
C4—C5—C6—C7179.2 (2)C14—C15—C16A—C11A−42.9 (6)
C10—C5—C6—C1179.9 (3)C16B—C15—C16A—C11A44.1 (5)
C4—C5—C6—C1−1.1 (4)O4—C15—C16B—C11B−144.5 (4)
C1—C6—C7—C8179.9 (3)C14—C15—C16B—C11B52.6 (5)
C5—C6—C7—C8−0.4 (4)C16A—C15—C16B—C11B−55.9 (5)
C6—C7—C8—C90.7 (4)O4—C15—C16B—C17−26.2 (7)
C6—C7—C8—C11A−175.6 (3)C14—C15—C16B—C17170.9 (3)
C6—C7—C8—C11B176.6 (3)C16A—C15—C16B—C1762.4 (6)
C7—C8—C9—C10−0.7 (4)C12—C11B—C16B—C15−66.7 (5)
C11A—C8—C9—C10174.1 (4)C8—C11B—C16B—C15174.1 (5)
C11B—C8—C9—C10−177.6 (3)C12—C11B—C16B—C17177.7 (5)
C8—C9—C10—C50.6 (5)C8—C11B—C16B—C1758.5 (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—O254.8 (8)
C7—C8—C11A—C16A132.9 (5)C11A—C16A—C17—O1123.3 (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—C16B64.4 (6)
C9—C8—C11A—C1278.3 (6)C15—C16B—C17—O2104.7 (5)
C11B—C8—C11A—C1261.4 (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—C12115.5 (5)C11B—C16B—C17—O135.9 (6)
C11A—C8—C11B—C12−76.8 (8)C15—C16B—C17—C16A−69.0 (6)
C7—C8—C11B—C16B57.3 (5)C11B—C16B—C17—C16A45.8 (5)
C9—C8—C11B—C16B−126.5 (4)C14—C13—C20—C21166.3 (3)
C11A—C8—C11B—C16B41.2 (6)C12—C13—C20—C21−15.2 (4)
C16B—C11B—C12—C1345.4 (6)C14—C13—C20—S1−17.2 (3)
C8—C11B—C12—C13161.1 (4)C12—C13—C20—S1161.28 (18)
C16B—C11B—C12—C11A−49.0 (6)C13—C20—C21—C22179.4 (3)
C8—C11B—C12—C11A66.7 (8)S1—C20—C21—C222.6 (3)
C8—C11A—C12—C11B−71.9 (8)C20—C21—C22—C23−2.8 (5)
C16A—C11A—C12—C11B47.5 (6)C21—C22—C23—S11.7 (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—C1421.7 (5)O2—C17—O1—C180.9 (6)
C11B—C12—C13—C20172.1 (4)C16A—C17—O1—C18179.6 (4)
C11A—C12—C13—C20−156.9 (4)C16B—C17—O1—C18−175.0 (4)
C20—C13—C14—C15173.4 (3)C19—C18—O1—C17104.5 (7)
C12—C13—C14—C15−5.0 (4)C4—C3—O3—C24−2.5 (6)
C13—C14—C15—O4178.6 (3)C2—C3—O3—C24177.4 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2629).

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