organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

6β-Chloro-5α-hydr­­oxy-20-oxopregnan-3β-yl acetate

aLaboratório de Química Farmacêutica, Faculdade de Farmácia, Universidade de Coimbra, P-3000-295 Coimbra, Portugal, and bCEMDRX, Departamento de Física, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, P-3004-516, Coimbra, Portugal
*Correspondence e-mail: jap@pollux.fis.uc.pt

(Received 12 June 2008; accepted 26 June 2008; online 5 July 2008)

The title steroid, C23H35ClO4, is a pregnane derivative prepared by ring opening of the corresponding 5α,6α-ep­oxy steroid with BiCl3. There are two symmetry-independent mol­ecules in the asymmetric unit that show no significant differences concerning bond lengths and angles. The conformation of the six-membered rings in both mol­ecules is close to a chair form, while the five-membered ring adopts an envelope conformation. All rings in both mol­ecules are trans-fused. The mol­ecules are held together by an extensive O—H⋯O hydrogen-bonding network.

Related literature

For related literature, see: Pinto et al. (2007a[Pinto, R. M. A., Ramos Silva, M., Matos Beja, A. & Salvador, J. A. R. (2007a). Acta Cryst. E63, o2138-o2139.],b[Pinto, R. M. A., Ramos Silva, M., Matos Beja, A., Salvador, J. A. R. & Paixão, J. A. (2007b). Acta Cryst. E63, o3321.],c[Pinto, R. M. A., Salvador, J. A. R. & Le Roux, C. (2007c). Tetrahedron, 63, 9221-9228.]); Spickett et al. (2000[Spickett, C. M., Jerlich, A., Panasenko, O. M., Arnhold, J., Pitt, A. R., Stelmaszynska, T. & Schaur, R. J. (2000). Acta Biochim. Pol. 47, 889-897.]); Mori et al. (1996[Mori, K., Nakayama, T. & Sakuma, M. (1996). Bioorg. Med. Chem. 4, 401-408.]), Iwashima et al. (2001[Iwashima, M., Nara, K., Nakamichi, Y. & Iguchi, K. (2001). Steroids, 66, 25-32.]), Dorta et al. (2004[Dorta, E., Díaz-Marrero, A. R., Cueto, M., D'Croz, L., Maté, J. L., San-Martín, A. & Darias, J. (2004). Tetrahedron Lett. 45, 915-918.]); Nittala et al. (1981[Nittala, S. S., Velde, V. V., Frolow, F. & Lavie, D. (1981). Phytochemistry, 20, 2547-2552.]); Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C23H35ClO4

  • Mr = 410.96

  • Monoclinic, P 21

  • a = 7.6862 (6) Å

  • b = 27.484 (2) Å

  • c = 11.1863 (9) Å

  • β = 110.094 (2)°

  • V = 2219.2 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 293 (2) K

  • 0.29 × 0.24 × 0.23 mm

Data collection
  • Bruker APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.895, Tmax = 0.956

  • 55742 measured reflections

  • 10978 independent reflections

  • 7889 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.117

  • S = 1.00

  • 10978 reflections

  • 515 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.26 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 5188 Friedel pairs

  • Flack parameter: 0.04 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5A—H5A⋯O20Ai 0.82 1.98 2.795 (2) 171
O5B—H5B⋯O20Bii 0.82 1.98 2.783 (2) 165
Symmetry codes: (i) x-1, y, z-1; (ii) x, y, z-1.

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In biological systems, hypochlorous acid, generated from H2O2 and chlorine by myeloperoxidase, is known to form chlorohydrin addition products with cholesterol (Spickett et al., 2000). The vicinal chlorohydrin group has been identified in other steroid natural compounds, such as blattellastanoside B, an aggregation pheromone of German cockroach Blattella germanica (Mori et al., 1996), marine steroids isolated from coral species (Iwashima et al., 2001 and Dorta et al., 2004) and chlorinated withanolides (Nittala et al., 1981). As part of our current interest on epoxysteroid chemistry we recently reported new processes for the regioselective ring opening of epoxides with bismuth salts (Pinto et al., 2007a). Applying this method to 5α,6α-epoxy-20-oxopregnan-3β-yl acetate we prepared the corresponding 6β-chloro-5α-hydroxysteroid (I) in 92% yield. The stereoselectivity of the nucleophilic ring opening of the 5α,6α-epoxide by BiCl3 was unequivocally demonstrated by this X-ray crystallographic study.

There are two symmetry independent molecules in the asymmetric unit (labeled A and B). In both molecules the conformation of the A ring is close to a chair form, as shown by the Cremer & Pople (1975) puckering parameters [A: Q= 0.570 (3) Å, θ = 5.8 (3)° and ϕ = 279 (3)°; B: Q= 0.578 (3) Å, θ = 4.9 (3)° and ϕ = 267 (3)°]. Rings B and C have slightly distorted chair conformations. The D-ring has a C13 envelope conformation with puckering parameters [A: q2 = 0.449 (2) Å and ϕ2 = 182.9 (3)°; B: q2 = 0.457 (2) Å and ϕ2 = 180.2 (3)°]. All rings in both molecules are fused trans. The acetoxy group at C3 is equatorial with respect to the A ring, and both substituents at the B ring are in axial position. The 17β-COCH3 substituent is equatorial with respect to the D-ring.

The molecules are hydrogen-bonded in infinite chains running parallel to [1 0 1] axis (molecule A) and [0 0 1] axis (molecule B) via the hydroxyl and the C20 carbonyl groups acting as donor and acceptor, respectively.

Related literature top

For related literature, see: Pinto et al. (2007a,b,c); Spickett et al. (2000); Mori et al. (1996), Iwashima et al. (2001), Dorta et al. (2004); Nittala et al. (1981); Cremer & Pople (1975).

Experimental top

5α,6α-epoxysteroids were prepared from the corresponding Δ5-steroid by epoxidation with m-chloroperbenzoic acid. The synthesis of 6β-chloro-5α-hydroxy-20-oxopregnan-3β-yl acetate (I) was efficiently accomplished by ring opening of the corresponding 5α,6α-epoxysteroid with BiCl3 in 1,4-dioxane at 80°C. The product was isolated in 92% yield (Pinto et al., 2007b). Recrystallization from methanol at room temperature gave colourless single crystals suitable for X-ray analysis. The analytical data of (I) are in accordance with published values (Pinto et al., 2007c).

Refinement top

H atoms were positioned geometrically and refined using a riding model using SHELXL97 default values (Uiso(H) = 1.2 Ueq(C) for CH and CH2 groups and Uĩso~(H) = 1.5 U~eq~(C) for CH3). The hydroxyl hydrogen atoms were refined with a distance restraint of 0.82 Å, starting from the difference map coordinates and with Uiso(H) = 1.5 Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97(Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97(Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of I showing the atom numbering scheme of the two symmetry independent molecules (A and B). Displacement ellipsoids are drawn at the 50% level.
6β-Chloro-5α-hydroxy-20-oxopregnan-3β-yl acetate top
Crystal data top
C23H35ClO4F(000) = 888
Mr = 410.96Dx = 1.230 Mg m3
Monoclinic, P21Melting point: 506 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 7.6862 (6) ÅCell parameters from 9965 reflections
b = 27.484 (2) Åθ = 2.4–26.1°
c = 11.1863 (9) ŵ = 0.20 mm1
β = 110.094 (2)°T = 293 K
V = 2219.2 (3) Å3Prism, colourless
Z = 40.29 × 0.24 × 0.23 mm
Data collection top
Bruker APEX CCD area-detector
diffractometer
10978 independent reflections
Radiation source: fine-focus sealed tube7889 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ϕ and ω scansθmax = 28.6°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 1010
Tmin = 0.895, Tmax = 0.956k = 3636
55742 measured reflectionsl = 1514
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0626P)2 + 0.239P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
10978 reflectionsΔρmax = 0.22 e Å3
515 parametersΔρmin = 0.26 e Å3
1 restraintAbsolute structure: Flack (1983), 5188 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (4)
Crystal data top
C23H35ClO4V = 2219.2 (3) Å3
Mr = 410.96Z = 4
Monoclinic, P21Mo Kα radiation
a = 7.6862 (6) ŵ = 0.20 mm1
b = 27.484 (2) ÅT = 293 K
c = 11.1863 (9) Å0.29 × 0.24 × 0.23 mm
β = 110.094 (2)°
Data collection top
Bruker APEX CCD area-detector
diffractometer
10978 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
7889 reflections with I > 2σ(I)
Tmin = 0.895, Tmax = 0.956Rint = 0.032
55742 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.117Δρmax = 0.22 e Å3
S = 1.00Δρmin = 0.26 e Å3
10978 reflectionsAbsolute structure: Flack (1983), 5188 Friedel pairs
515 parametersAbsolute structure parameter: 0.04 (4)
1 restraint
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
xyzUiso*/Ueq
C1A0.4116 (3)0.18353 (9)0.7110 (2)0.0504 (6)
H1A10.54180.19130.75170.060*
H1A20.40320.15020.68140.060*
C2A0.3296 (4)0.21710 (10)0.5962 (2)0.0581 (6)
H2A10.35240.25070.62350.070*
H2A20.39030.21100.53470.070*
C3A0.1236 (4)0.20907 (9)0.5339 (2)0.0538 (6)
H3A0.10080.17780.48930.065*
C4A0.0213 (3)0.21092 (9)0.6284 (2)0.0508 (6)
H4A10.10750.20220.58540.061*
H4A20.02500.24390.66030.061*
C5A0.1066 (3)0.17630 (8)0.7399 (2)0.0412 (5)
C6A0.0100 (3)0.17224 (8)0.8275 (2)0.0460 (5)
H6A0.12850.15760.77620.055*
C7A0.0739 (3)0.13888 (8)0.9396 (2)0.0437 (5)
H7A10.06140.10550.90980.052*
H7A20.00580.14220.99780.052*
C8A0.2773 (3)0.14963 (8)1.01065 (19)0.0374 (4)
H8A0.28720.18181.05000.045*
C9A0.3890 (3)0.14992 (8)0.91948 (19)0.0378 (4)
H9A0.37190.11780.87910.045*
C10A0.3142 (3)0.18762 (7)0.81034 (19)0.0388 (4)
C11A0.5973 (3)0.15552 (10)0.9918 (2)0.0520 (6)
H11A0.66350.15060.93300.062*
H11B0.62180.18851.02410.062*
C12A0.6718 (3)0.11993 (10)1.1028 (2)0.0490 (5)
H12A0.80040.12761.14990.059*
H12B0.66670.08711.06970.059*
C13A0.5605 (3)0.12211 (8)1.19318 (19)0.0394 (4)
C14A0.3578 (3)0.11236 (7)1.11474 (19)0.0363 (4)
H14A0.35660.08141.07100.044*
C15A0.2637 (3)0.10218 (9)1.2122 (2)0.0468 (5)
H15A0.16100.07981.17770.056*
H15B0.21740.13211.23630.056*
C16A0.4139 (3)0.07964 (9)1.3267 (2)0.0506 (5)
H16A0.38080.04671.34130.061*
H16B0.43110.09871.40290.061*
C17A0.5914 (3)0.07993 (8)1.29204 (19)0.0430 (5)
H17A0.59650.04931.24860.052*
C18A0.5863 (4)0.17114 (9)1.2621 (2)0.0546 (6)
H18A0.71370.17491.31500.082*
H18B0.50940.17231.31390.082*
H18C0.55190.19691.20050.082*
C19A0.3459 (3)0.23976 (8)0.8643 (2)0.0502 (5)
H19A0.26620.26180.80340.075*
H19B0.47280.24890.88140.075*
H19C0.31850.24100.94180.075*
C2OA0.7669 (3)0.08453 (9)1.4041 (2)0.0501 (6)
C21A0.9416 (4)0.06847 (15)1.3866 (3)0.0835 (10)
H21A0.96640.08891.32470.125*
H21B0.92890.03531.35780.125*
H21C1.04220.07091.46620.125*
C22A0.0374 (4)0.24333 (11)0.3249 (3)0.0637 (7)
C23A0.0545 (5)0.28581 (14)0.2463 (3)0.0882 (10)
H23A0.10980.27590.15910.132*
H23B0.03570.31080.25260.132*
H23C0.14870.29820.27640.132*
Cl6A0.06419 (9)0.23082 (2)0.88169 (7)0.06487 (18)
O3A0.0438 (3)0.24819 (6)0.44440 (16)0.0661 (5)
O5A0.1045 (2)0.12731 (5)0.69162 (15)0.0487 (4)
H5A0.00040.12090.64220.073*
O20A0.7689 (3)0.10243 (8)1.50390 (16)0.0668 (5)
O22A0.0948 (5)0.20927 (11)0.2873 (2)0.1296 (13)
C1B0.4187 (3)0.40216 (10)0.6303 (2)0.0553 (6)
H1B10.39660.43580.60280.066*
H1B20.33090.39370.67180.066*
C2B0.3846 (4)0.36956 (11)0.5131 (2)0.0642 (7)
H2B10.39030.33570.53880.077*
H2B20.26140.37580.45290.077*
C3B0.5266 (4)0.37864 (9)0.4488 (2)0.0548 (6)
H3B0.50620.41090.40920.066*
C4B0.7206 (3)0.37494 (9)0.5377 (2)0.0489 (5)
H4B10.80520.38370.49380.059*
H4B20.74680.34170.56770.059*
C5B0.7489 (3)0.40931 (7)0.6515 (2)0.0422 (5)
C6B0.9517 (3)0.41362 (8)0.7339 (2)0.0445 (5)
H6B1.01670.42780.68070.053*
C7B0.9786 (3)0.44826 (8)0.8449 (2)0.0436 (5)
H7B10.95520.48120.81250.052*
H7B21.10650.44660.90130.052*
C8B0.8516 (3)0.43712 (8)0.9215 (2)0.0370 (4)
H8B0.88570.40530.96230.044*
C9B0.6487 (3)0.43539 (8)0.8352 (2)0.0397 (5)
H9B0.62020.46740.79430.048*
C10B0.6149 (3)0.39743 (8)0.7259 (2)0.0417 (5)
C11B0.5181 (3)0.42880 (10)0.9126 (2)0.0518 (6)
H11C0.39110.43240.85560.062*
H11D0.53200.39590.94620.062*
C12B0.5521 (3)0.46465 (9)1.0234 (2)0.0465 (5)
H12C0.51870.49720.99020.056*
H12D0.47460.45601.07270.056*
C13B0.7535 (3)0.46384 (7)1.10859 (19)0.0368 (4)
C14B0.8724 (3)0.47500 (7)1.02440 (19)0.0366 (4)
H14B0.82410.50550.97990.044*
C15B1.0630 (3)0.48659 (9)1.1175 (2)0.0467 (5)
H15C1.12460.51051.08220.056*
H15D1.13890.45751.13900.056*
C16B1.0279 (3)0.50710 (9)1.2361 (2)0.0478 (5)
H16C1.08960.48721.31020.057*
H16D1.07450.54011.25320.057*
C17B0.8184 (3)0.50615 (8)1.20557 (19)0.0406 (5)
H17B0.76720.53651.16140.049*
C18B0.8034 (4)0.41460 (8)1.1769 (2)0.0503 (6)
H18D0.93200.41451.22930.075*
H18E0.78070.38901.11500.075*
H18F0.72890.40951.22930.075*
C19B0.6383 (4)0.34516 (9)0.7812 (2)0.0549 (6)
H19D0.52930.33610.79930.082*
H19E0.74390.34410.85820.082*
H19F0.65620.32290.72040.082*
C20B0.7553 (3)0.50139 (8)1.3198 (2)0.0471 (5)
C21B0.5746 (4)0.52302 (12)1.3101 (3)0.0698 (8)
H21D0.48290.51381.23060.105*
H21E0.58550.55781.31430.105*
H21F0.53830.51151.37900.105*
C22B0.3880 (4)0.34971 (11)0.2356 (2)0.0614 (7)
C23B0.3812 (5)0.30944 (13)0.1450 (3)0.0813 (9)
H23D0.26730.31120.07400.122*
H23E0.38820.27880.18740.122*
H23F0.48390.31240.11510.122*
Cl6B1.05925 (9)0.35550 (2)0.79004 (6)0.06012 (16)
O3B0.5069 (3)0.34127 (6)0.35021 (15)0.0634 (5)
O5B0.7007 (2)0.45778 (5)0.60311 (15)0.0505 (4)
H5B0.76210.46530.55880.076*
O20B0.8475 (3)0.48017 (7)1.41448 (15)0.0627 (5)
O22B0.3020 (4)0.38579 (10)0.2084 (2)0.1228 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0510 (14)0.0574 (15)0.0419 (12)0.0034 (10)0.0150 (11)0.0095 (10)
C2A0.0651 (16)0.0623 (16)0.0487 (13)0.0012 (12)0.0217 (12)0.0173 (12)
C3A0.0678 (16)0.0402 (12)0.0417 (12)0.0063 (11)0.0038 (11)0.0096 (10)
C4A0.0481 (13)0.0481 (13)0.0439 (12)0.0025 (10)0.0000 (10)0.0076 (10)
C5A0.0440 (12)0.0361 (11)0.0366 (11)0.0005 (9)0.0049 (9)0.0040 (9)
C6A0.0350 (11)0.0461 (12)0.0509 (13)0.0010 (9)0.0072 (10)0.0009 (10)
C7A0.0334 (10)0.0491 (13)0.0458 (12)0.0041 (9)0.0101 (9)0.0067 (10)
C8A0.0324 (10)0.0375 (11)0.0386 (10)0.0017 (8)0.0073 (8)0.0023 (8)
C9A0.0327 (10)0.0417 (11)0.0359 (10)0.0035 (8)0.0079 (8)0.0027 (9)
C10A0.0402 (11)0.0362 (11)0.0362 (10)0.0038 (8)0.0084 (9)0.0034 (8)
C11A0.0333 (11)0.0733 (16)0.0458 (12)0.0055 (11)0.0091 (10)0.0148 (12)
C12A0.0332 (11)0.0665 (15)0.0431 (12)0.0015 (10)0.0077 (9)0.0109 (11)
C13A0.0355 (10)0.0408 (11)0.0368 (10)0.0050 (9)0.0060 (9)0.0015 (9)
C14A0.0377 (10)0.0349 (10)0.0337 (10)0.0053 (8)0.0088 (8)0.0009 (8)
C15A0.0477 (12)0.0506 (13)0.0435 (12)0.0040 (10)0.0176 (10)0.0046 (10)
C16A0.0590 (14)0.0536 (13)0.0390 (12)0.0064 (11)0.0167 (11)0.0081 (10)
C17A0.0498 (12)0.0391 (11)0.0326 (10)0.0016 (9)0.0047 (9)0.0013 (9)
C18A0.0595 (15)0.0458 (13)0.0469 (13)0.0124 (11)0.0032 (11)0.0014 (10)
C19A0.0530 (13)0.0447 (13)0.0477 (12)0.0119 (10)0.0105 (11)0.0026 (10)
C2OA0.0514 (14)0.0510 (13)0.0387 (12)0.0009 (10)0.0037 (10)0.0109 (10)
C21A0.0609 (18)0.117 (3)0.0589 (17)0.0325 (18)0.0034 (14)0.0123 (17)
C22A0.0743 (18)0.0674 (18)0.0447 (14)0.0041 (14)0.0144 (13)0.0139 (13)
C23A0.103 (3)0.086 (2)0.0648 (18)0.0154 (19)0.0161 (18)0.0360 (17)
Cl6A0.0620 (4)0.0579 (4)0.0788 (4)0.0118 (3)0.0295 (3)0.0038 (3)
O3A0.0924 (14)0.0530 (11)0.0446 (9)0.0147 (9)0.0126 (9)0.0137 (8)
O5A0.0499 (9)0.0404 (8)0.0420 (8)0.0033 (7)0.0018 (7)0.0026 (7)
O20A0.0627 (11)0.0850 (13)0.0395 (9)0.0035 (10)0.0006 (8)0.0078 (9)
O22A0.224 (4)0.110 (2)0.0622 (14)0.076 (2)0.0589 (19)0.0231 (14)
C1B0.0473 (14)0.0706 (16)0.0489 (13)0.0045 (12)0.0174 (11)0.0087 (12)
C2B0.0616 (16)0.0720 (18)0.0508 (14)0.0077 (13)0.0089 (13)0.0108 (13)
C3B0.0785 (18)0.0418 (12)0.0449 (13)0.0066 (11)0.0221 (13)0.0081 (10)
C4B0.0595 (15)0.0458 (12)0.0451 (12)0.0028 (10)0.0226 (11)0.0054 (10)
C5B0.0565 (13)0.0331 (11)0.0426 (11)0.0013 (9)0.0242 (10)0.0004 (9)
C6B0.0485 (13)0.0427 (12)0.0519 (13)0.0017 (9)0.0296 (11)0.0033 (10)
C7B0.0465 (12)0.0420 (12)0.0519 (13)0.0060 (9)0.0290 (11)0.0067 (10)
C8B0.0393 (11)0.0377 (10)0.0398 (11)0.0008 (8)0.0210 (9)0.0011 (8)
C9B0.0401 (11)0.0441 (11)0.0390 (11)0.0026 (9)0.0190 (9)0.0020 (9)
C10B0.0455 (12)0.0425 (12)0.0398 (11)0.0039 (9)0.0182 (10)0.0022 (9)
C11B0.0466 (13)0.0704 (16)0.0444 (12)0.0124 (11)0.0234 (11)0.0092 (11)
C12B0.0395 (12)0.0643 (15)0.0417 (11)0.0011 (10)0.0217 (10)0.0007 (10)
C13B0.0416 (11)0.0381 (11)0.0352 (10)0.0018 (9)0.0189 (9)0.0001 (8)
C14B0.0389 (11)0.0349 (10)0.0397 (10)0.0002 (8)0.0184 (9)0.0025 (8)
C15B0.0403 (12)0.0485 (13)0.0523 (13)0.0028 (10)0.0172 (10)0.0068 (10)
C16B0.0505 (13)0.0497 (13)0.0398 (11)0.0035 (10)0.0113 (10)0.0023 (10)
C17B0.0515 (12)0.0384 (11)0.0351 (10)0.0024 (9)0.0189 (9)0.0030 (8)
C18B0.0686 (16)0.0396 (12)0.0452 (12)0.0035 (11)0.0229 (12)0.0049 (10)
C19B0.0709 (16)0.0452 (13)0.0539 (14)0.0161 (11)0.0281 (13)0.0035 (10)
C20B0.0641 (15)0.0418 (12)0.0395 (12)0.0050 (10)0.0230 (11)0.0064 (10)
C21B0.0766 (19)0.086 (2)0.0576 (15)0.0125 (15)0.0374 (15)0.0009 (14)
C22B0.0684 (16)0.0633 (17)0.0448 (13)0.0109 (14)0.0097 (12)0.0091 (12)
C23B0.091 (2)0.083 (2)0.0593 (17)0.0097 (18)0.0113 (16)0.0246 (16)
Cl6B0.0586 (4)0.0533 (3)0.0693 (4)0.0115 (3)0.0231 (3)0.0046 (3)
O3B0.0874 (13)0.0495 (10)0.0435 (9)0.0127 (9)0.0102 (9)0.0098 (7)
O5B0.0747 (11)0.0405 (8)0.0456 (9)0.0064 (8)0.0327 (8)0.0044 (7)
O20B0.0801 (13)0.0724 (12)0.0388 (9)0.0022 (10)0.0244 (9)0.0072 (8)
O22B0.154 (3)0.0963 (18)0.0704 (14)0.0630 (19)0.0223 (16)0.0202 (13)
Geometric parameters (Å, º) top
C1A—C2A1.530 (3)C1B—C10B1.525 (3)
C1A—C10A1.542 (3)C1B—C2B1.534 (3)
C1A—H1A10.9700C1B—H1B10.9700
C1A—H1A20.9700C1B—H1B20.9700
C2A—C3A1.510 (4)C2B—C3B1.521 (4)
C2A—H2A10.9700C2B—H2B10.9700
C2A—H2A20.9700C2B—H2B20.9700
C3A—O3A1.454 (3)C3B—O3B1.476 (3)
C3A—C4A1.520 (4)C3B—C4B1.484 (4)
C3A—H3A0.9800C3B—H3B0.9800
C4A—C5A1.526 (3)C4B—C5B1.539 (3)
C4A—H4A10.9700C4B—H4B10.9700
C4A—H4A20.9700C4B—H4B20.9700
C5A—O5A1.449 (3)C5B—O5B1.438 (3)
C5A—C6A1.542 (3)C5B—C6B1.518 (3)
C5A—C10A1.549 (3)C5B—C10B1.566 (3)
C6A—C7A1.508 (3)C6B—C7B1.521 (3)
C6A—Cl6A1.819 (2)C6B—Cl6B1.809 (2)
C6A—H6A0.9800C6B—H6B0.9800
C7A—C8A1.520 (3)C7B—C8B1.535 (3)
C7A—H7A10.9700C7B—H7B10.9700
C7A—H7A20.9700C7B—H7B20.9700
C8A—C14A1.514 (3)C8B—C14B1.519 (3)
C8A—C9A1.542 (3)C8B—C9B1.527 (3)
C8A—H8A0.9800C8B—H8B0.9800
C9A—C11A1.534 (3)C9B—C11B1.545 (3)
C9A—C10A1.553 (3)C9B—C10B1.560 (3)
C9A—H9A0.9800C9B—H9B0.9800
C10A—C19A1.542 (3)C10B—C19B1.550 (3)
C11A—C12A1.529 (3)C11B—C12B1.534 (3)
C11A—H11A0.9700C11B—H11C0.9700
C11A—H11B0.9700C11B—H11D0.9700
C12A—C13A1.533 (3)C12B—C13B1.513 (3)
C12A—H12A0.9700C12B—H12C0.9700
C12A—H12B0.9700C12B—H12D0.9700
C13A—C14A1.527 (3)C13B—C18B1.537 (3)
C13A—C18A1.531 (3)C13B—C17B1.551 (3)
C13A—C17A1.563 (3)C13B—C14B1.551 (3)
C14A—C15A1.527 (3)C14B—C15B1.512 (3)
C14A—H14A0.9800C14B—H14B0.9800
C15A—C16A1.530 (3)C15B—C16B1.548 (3)
C15A—H15A0.9700C15B—H15C0.9700
C15A—H15B0.9700C15B—H15D0.9700
C16A—C17A1.541 (3)C16B—C17B1.527 (3)
C16A—H16A0.9700C16B—H16C0.9700
C16A—H16B0.9700C16B—H16D0.9700
C17A—C2OA1.498 (3)C17B—C20B1.520 (3)
C17A—H17A0.9800C17B—H17B0.9800
C18A—H18A0.9600C18B—H18D0.9600
C18A—H18B0.9600C18B—H18E0.9600
C18A—H18C0.9600C18B—H18F0.9600
C19A—H19A0.9600C19B—H19D0.9600
C19A—H19B0.9600C19B—H19E0.9600
C19A—H19C0.9600C19B—H19F0.9600
C2OA—O20A1.215 (3)C20B—O20B1.204 (3)
C2OA—C21A1.489 (4)C20B—C21B1.480 (4)
C21A—H21A0.9600C21B—H21D0.9600
C21A—H21B0.9600C21B—H21E0.9600
C21A—H21C0.9600C21B—H21F0.9600
C22A—O22A1.173 (4)C22B—O22B1.173 (4)
C22A—O3A1.327 (3)C22B—O3B1.315 (3)
C22A—C23A1.486 (4)C22B—C23B1.490 (4)
C23A—H23A0.9600C23B—H23D0.9600
C23A—H23B0.9600C23B—H23E0.9600
C23A—H23C0.9600C23B—H23F0.9600
O5A—H5A0.8200O5B—H5B0.8200
C2A—C1A—C10A113.5 (2)C10B—C1B—C2B112.8 (2)
C2A—C1A—H1A1108.9C10B—C1B—H1B1109.0
C10A—C1A—H1A1108.9C2B—C1B—H1B1109.0
C2A—C1A—H1A2108.9C10B—C1B—H1B2109.0
C10A—C1A—H1A2108.9C2B—C1B—H1B2109.0
H1A1—C1A—H1A2107.7H1B1—C1B—H1B2107.8
C3A—C2A—C1A111.3 (2)C3B—C2B—C1B111.6 (2)
C3A—C2A—H2A1109.4C3B—C2B—H2B1109.3
C1A—C2A—H2A1109.4C1B—C2B—H2B1109.3
C3A—C2A—H2A2109.4C3B—C2B—H2B2109.3
C1A—C2A—H2A2109.4C1B—C2B—H2B2109.3
H2A1—C2A—H2A2108.0H2B1—C2B—H2B2108.0
O3A—C3A—C2A109.7 (2)O3B—C3B—C4B105.94 (19)
O3A—C3A—C4A104.9 (2)O3B—C3B—C2B109.5 (2)
C2A—C3A—C4A112.7 (2)C4B—C3B—C2B113.0 (2)
O3A—C3A—H3A109.8O3B—C3B—H3B109.4
C2A—C3A—H3A109.8C4B—C3B—H3B109.4
C4A—C3A—H3A109.8C2B—C3B—H3B109.4
C3A—C4A—C5A111.55 (19)C3B—C4B—C5B109.63 (18)
C3A—C4A—H4A1109.3C3B—C4B—H4B1109.7
C5A—C4A—H4A1109.3C5B—C4B—H4B1109.7
C3A—C4A—H4A2109.3C3B—C4B—H4B2109.7
C5A—C4A—H4A2109.3C5B—C4B—H4B2109.7
H4A1—C4A—H4A2108.0H4B1—C4B—H4B2108.2
O5A—C5A—C4A109.18 (17)O5B—C5B—C6B103.56 (17)
O5A—C5A—C6A103.59 (17)O5B—C5B—C4B108.22 (17)
C4A—C5A—C6A112.58 (18)C6B—C5B—C4B111.97 (18)
O5A—C5A—C10A104.70 (16)O5B—C5B—C10B105.17 (16)
C4A—C5A—C10A111.65 (17)C6B—C5B—C10B114.75 (17)
C6A—C5A—C10A114.38 (17)C4B—C5B—C10B112.33 (18)
C7A—C6A—C5A113.38 (18)C5B—C6B—C7B111.59 (17)
C7A—C6A—Cl6A110.03 (16)C5B—C6B—Cl6B113.16 (15)
C5A—C6A—Cl6A113.42 (16)C7B—C6B—Cl6B110.58 (16)
C7A—C6A—H6A106.5C5B—C6B—H6B107.1
C5A—C6A—H6A106.5C7B—C6B—H6B107.1
Cl6A—C6A—H6A106.5Cl6B—C6B—H6B107.1
C6A—C7A—C8A112.70 (17)C6B—C7B—C8B113.37 (17)
C6A—C7A—H7A1109.1C6B—C7B—H7B1108.9
C8A—C7A—H7A1109.1C8B—C7B—H7B1108.9
C6A—C7A—H7A2109.1C6B—C7B—H7B2108.9
C8A—C7A—H7A2109.1C8B—C7B—H7B2108.9
H7A1—C7A—H7A2107.8H7B1—C7B—H7B2107.7
C14A—C8A—C7A110.23 (16)C14B—C8B—C9B108.60 (16)
C14A—C8A—C9A109.80 (16)C14B—C8B—C7B111.40 (17)
C7A—C8A—C9A111.18 (16)C9B—C8B—C7B111.14 (16)
C14A—C8A—H8A108.5C14B—C8B—H8B108.5
C7A—C8A—H8A108.5C9B—C8B—H8B108.5
C9A—C8A—H8A108.5C7B—C8B—H8B108.5
C11A—C9A—C8A111.66 (17)C8B—C9B—C11B111.64 (16)
C11A—C9A—C10A112.65 (17)C8B—C9B—C10B112.05 (17)
C8A—C9A—C10A112.55 (16)C11B—C9B—C10B113.30 (18)
C11A—C9A—H9A106.5C8B—C9B—H9B106.4
C8A—C9A—H9A106.5C11B—C9B—H9B106.4
C10A—C9A—H9A106.5C10B—C9B—H9B106.4
C1A—C10A—C19A107.42 (18)C1B—C10B—C19B108.07 (19)
C1A—C10A—C5A106.78 (17)C1B—C10B—C9B110.56 (18)
C19A—C10A—C5A112.49 (18)C19B—C10B—C9B109.98 (17)
C1A—C10A—C9A112.19 (17)C1B—C10B—C5B106.37 (17)
C19A—C10A—C9A110.26 (17)C19B—C10B—C5B113.47 (18)
C5A—C10A—C9A107.72 (16)C9B—C10B—C5B108.34 (17)
C12A—C11A—C9A113.32 (18)C12B—C11B—C9B114.46 (19)
C12A—C11A—H11A108.9C12B—C11B—H11C108.6
C9A—C11A—H11A108.9C9B—C11B—H11C108.6
C12A—C11A—H11B108.9C12B—C11B—H11D108.6
C9A—C11A—H11B108.9C9B—C11B—H11D108.6
H11A—C11A—H11B107.7H11C—C11B—H11D107.6
C11A—C12A—C13A111.88 (19)C13B—C12B—C11B110.67 (18)
C11A—C12A—H12A109.2C13B—C12B—H12C109.5
C13A—C12A—H12A109.2C11B—C12B—H12C109.5
C11A—C12A—H12B109.2C13B—C12B—H12D109.5
C13A—C12A—H12B109.2C11B—C12B—H12D109.5
H12A—C12A—H12B107.9H12C—C12B—H12D108.1
C14A—C13A—C12A107.73 (16)C12B—C13B—C18B110.66 (18)
C14A—C13A—C18A111.95 (18)C12B—C13B—C17B116.29 (17)
C12A—C13A—C18A111.19 (19)C18B—C13B—C17B110.29 (17)
C14A—C13A—C17A98.83 (16)C12B—C13B—C14B107.65 (16)
C12A—C13A—C17A116.99 (18)C18B—C13B—C14B112.18 (17)
C18A—C13A—C17A109.56 (17)C17B—C13B—C14B99.29 (15)
C8A—C14A—C15A120.28 (18)C15B—C14B—C8B119.41 (17)
C8A—C14A—C13A112.94 (16)C15B—C14B—C13B104.89 (16)
C15A—C14A—C13A105.21 (16)C8B—C14B—C13B113.20 (17)
C8A—C14A—H14A105.8C15B—C14B—H14B106.1
C15A—C14A—H14A105.8C8B—C14B—H14B106.1
C13A—C14A—H14A105.8C13B—C14B—H14B106.1
C14A—C15A—C16A105.40 (18)C14B—C15B—C16B104.71 (17)
C14A—C15A—H15A110.7C14B—C15B—H15C110.8
C16A—C15A—H15A110.7C16B—C15B—H15C110.8
C14A—C15A—H15B110.7C14B—C15B—H15D110.8
C16A—C15A—H15B110.7C16B—C15B—H15D110.8
H15A—C15A—H15B108.8H15C—C15B—H15D108.9
C15A—C16A—C17A105.41 (17)C17B—C16B—C15B106.46 (17)
C15A—C16A—H16A110.7C17B—C16B—H16C110.4
C17A—C16A—H16A110.7C15B—C16B—H16C110.4
C15A—C16A—H16B110.7C17B—C16B—H16D110.4
C17A—C16A—H16B110.7C15B—C16B—H16D110.4
H16A—C16A—H16B108.8H16C—C16B—H16D108.6
C2OA—C17A—C16A114.21 (18)C20B—C17B—C16B115.49 (19)
C2OA—C17A—C13A113.82 (18)C20B—C17B—C13B113.85 (17)
C16A—C17A—C13A104.44 (17)C16B—C17B—C13B103.31 (17)
C2OA—C17A—H17A108.0C20B—C17B—H17B107.9
C16A—C17A—H17A108.0C16B—C17B—H17B107.9
C13A—C17A—H17A108.0C13B—C17B—H17B107.9
C13A—C18A—H18A109.5C13B—C18B—H18D109.5
C13A—C18A—H18B109.5C13B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C13A—C18A—H18C109.5C13B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C10A—C19A—H19A109.5C10B—C19B—H19D109.5
C10A—C19A—H19B109.5C10B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C10A—C19A—H19C109.5C10B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
O20A—C2OA—C21A120.9 (2)O20B—C20B—C21B120.9 (2)
O20A—C2OA—C17A121.8 (2)O20B—C20B—C17B121.3 (2)
C21A—C2OA—C17A117.3 (2)C21B—C20B—C17B117.8 (2)
C2OA—C21A—H21A109.5C20B—C21B—H21D109.5
C2OA—C21A—H21B109.5C20B—C21B—H21E109.5
H21A—C21A—H21B109.5H21D—C21B—H21E109.5
C2OA—C21A—H21C109.5C20B—C21B—H21F109.5
H21A—C21A—H21C109.5H21D—C21B—H21F109.5
H21B—C21A—H21C109.5H21E—C21B—H21F109.5
O22A—C22A—O3A123.6 (3)O22B—C22B—O3B122.9 (2)
O22A—C22A—C23A125.1 (3)O22B—C22B—C23B124.6 (3)
O3A—C22A—C23A111.2 (3)O3B—C22B—C23B112.5 (2)
C22A—C23A—H23A109.5C22B—C23B—H23D109.5
C22A—C23A—H23B109.5C22B—C23B—H23E109.5
H23A—C23A—H23B109.5H23D—C23B—H23E109.5
C22A—C23A—H23C109.5C22B—C23B—H23F109.5
H23A—C23A—H23C109.5H23D—C23B—H23F109.5
H23B—C23A—H23C109.5H23E—C23B—H23F109.5
C22A—O3A—C3A118.7 (2)C22B—O3B—C3B117.69 (19)
C5A—O5A—H5A109.5C5B—O5B—H5B109.5
C10A—C1A—C2A—C3A54.8 (3)C10B—C1B—C2B—C3B54.8 (3)
C1A—C2A—C3A—O3A167.5 (2)C1B—C2B—C3B—O3B170.9 (2)
C1A—C2A—C3A—C4A51.0 (3)C1B—C2B—C3B—C4B53.1 (3)
O3A—C3A—C4A—C5A172.38 (18)O3B—C3B—C4B—C5B174.52 (18)
C2A—C3A—C4A—C5A53.1 (3)C2B—C3B—C4B—C5B54.7 (3)
C3A—C4A—C5A—O5A57.7 (2)C3B—C4B—C5B—O5B56.8 (2)
C3A—C4A—C5A—C6A172.21 (19)C3B—C4B—C5B—C6B170.28 (19)
C3A—C4A—C5A—C10A57.5 (2)C3B—C4B—C5B—C10B58.9 (2)
O5A—C5A—C6A—C7A63.2 (2)O5B—C5B—C6B—C7B62.7 (2)
C4A—C5A—C6A—C7A178.95 (19)C4B—C5B—C6B—C7B179.12 (17)
C10A—C5A—C6A—C7A50.1 (2)C10B—C5B—C6B—C7B51.3 (2)
O5A—C5A—C6A—Cl6A170.33 (14)O5B—C5B—C6B—Cl6B171.77 (12)
C4A—C5A—C6A—Cl6A52.5 (2)C4B—C5B—C6B—Cl6B55.4 (2)
C10A—C5A—C6A—Cl6A76.3 (2)C10B—C5B—C6B—Cl6B74.2 (2)
C5A—C6A—C7A—C8A49.3 (3)C5B—C6B—C7B—C8B50.8 (2)
Cl6A—C6A—C7A—C8A78.9 (2)Cl6B—C6B—C7B—C8B76.1 (2)
C6A—C7A—C8A—C14A175.11 (18)C6B—C7B—C8B—C14B175.41 (19)
C6A—C7A—C8A—C9A53.1 (2)C6B—C7B—C8B—C9B54.2 (2)
C14A—C8A—C9A—C11A51.9 (2)C14B—C8B—C9B—C11B52.0 (2)
C7A—C8A—C9A—C11A174.15 (19)C7B—C8B—C9B—C11B174.88 (18)
C14A—C8A—C9A—C10A179.76 (17)C14B—C8B—C9B—C10B179.71 (17)
C7A—C8A—C9A—C10A58.0 (2)C7B—C8B—C9B—C10B56.8 (2)
C2A—C1A—C10A—C19A63.7 (3)C2B—C1B—C10B—C19B65.9 (3)
C2A—C1A—C10A—C5A57.1 (2)C2B—C1B—C10B—C9B173.7 (2)
C2A—C1A—C10A—C9A174.93 (19)C2B—C1B—C10B—C5B56.3 (3)
O5A—C5A—C10A—C1A60.0 (2)C8B—C9B—C10B—C1B171.23 (18)
C4A—C5A—C10A—C1A58.0 (2)C11B—C9B—C10B—C1B61.4 (2)
C6A—C5A—C10A—C1A172.66 (18)C8B—C9B—C10B—C19B69.5 (2)
O5A—C5A—C10A—C19A177.57 (17)C11B—C9B—C10B—C19B57.9 (2)
C4A—C5A—C10A—C19A59.6 (2)C8B—C9B—C10B—C5B55.0 (2)
C6A—C5A—C10A—C19A69.8 (2)C11B—C9B—C10B—C5B177.55 (19)
O5A—C5A—C10A—C9A60.7 (2)O5B—C5B—C10B—C1B58.7 (2)
C4A—C5A—C10A—C9A178.72 (18)C6B—C5B—C10B—C1B171.78 (18)
C6A—C5A—C10A—C9A52.0 (2)C4B—C5B—C10B—C1B58.8 (2)
C11A—C9A—C10A—C1A59.4 (2)O5B—C5B—C10B—C19B177.35 (18)
C8A—C9A—C10A—C1A173.28 (17)C6B—C5B—C10B—C19B69.5 (2)
C11A—C9A—C10A—C19A60.3 (2)C4B—C5B—C10B—C19B59.9 (2)
C8A—C9A—C10A—C19A67.0 (2)O5B—C5B—C10B—C9B60.2 (2)
C11A—C9A—C10A—C5A176.62 (19)C6B—C5B—C10B—C9B52.9 (2)
C8A—C9A—C10A—C5A56.1 (2)C4B—C5B—C10B—C9B177.70 (18)
C8A—C9A—C11A—C12A50.0 (3)C8B—C9B—C11B—C12B50.6 (3)
C10A—C9A—C11A—C12A177.81 (19)C10B—C9B—C11B—C12B178.2 (2)
C9A—C11A—C12A—C13A52.9 (3)C9B—C11B—C12B—C13B53.0 (3)
C11A—C12A—C13A—C14A56.2 (2)C11B—C12B—C13B—C18B66.9 (2)
C11A—C12A—C13A—C18A66.8 (2)C11B—C12B—C13B—C17B166.29 (18)
C11A—C12A—C13A—C17A166.34 (18)C11B—C12B—C13B—C14B56.0 (2)
C7A—C8A—C14A—C15A52.7 (3)C9B—C8B—C14B—C15B175.70 (17)
C9A—C8A—C14A—C15A175.50 (18)C7B—C8B—C14B—C15B53.0 (2)
C7A—C8A—C14A—C13A177.93 (17)C9B—C8B—C14B—C13B60.1 (2)
C9A—C8A—C14A—C13A59.3 (2)C7B—C8B—C14B—C13B177.21 (18)
C12A—C13A—C14A—C8A60.9 (2)C12B—C13B—C14B—C15B165.70 (18)
C18A—C13A—C14A—C8A61.6 (2)C18B—C13B—C14B—C15B72.3 (2)
C17A—C13A—C14A—C8A176.94 (17)C17B—C13B—C14B—C15B44.17 (19)
C12A—C13A—C14A—C15A166.02 (18)C12B—C13B—C14B—C8B62.5 (2)
C18A—C13A—C14A—C15A71.4 (2)C18B—C13B—C14B—C8B59.5 (2)
C17A—C13A—C14A—C15A43.9 (2)C17B—C13B—C14B—C8B176.00 (16)
C8A—C14A—C15A—C16A158.59 (19)C8B—C14B—C15B—C16B156.10 (19)
C13A—C14A—C15A—C16A29.8 (2)C13B—C14B—C15B—C16B27.9 (2)
C14A—C15A—C16A—C17A2.4 (2)C14B—C15B—C16B—C17B0.2 (2)
C15A—C16A—C17A—C2OA149.9 (2)C15B—C16B—C17B—C20B152.35 (19)
C15A—C16A—C17A—C13A25.0 (2)C15B—C16B—C17B—C13B27.4 (2)
C14A—C13A—C17A—C2OA167.17 (19)C12B—C13B—C17B—C20B75.8 (2)
C12A—C13A—C17A—C2OA77.7 (2)C18B—C13B—C17B—C20B51.3 (2)
C18A—C13A—C17A—C2OA50.0 (3)C14B—C13B—C17B—C20B169.18 (18)
C14A—C13A—C17A—C16A42.0 (2)C12B—C13B—C17B—C16B158.21 (17)
C12A—C13A—C17A—C16A157.10 (19)C18B—C13B—C17B—C16B74.8 (2)
C18A—C13A—C17A—C16A75.2 (2)C14B—C13B—C17B—C16B43.16 (19)
C16A—C17A—C2OA—O20A23.3 (3)C16B—C17B—C20B—O20B29.8 (3)
C13A—C17A—C2OA—O20A96.5 (3)C13B—C17B—C20B—O20B89.5 (3)
C16A—C17A—C2OA—C21A159.6 (3)C16B—C17B—C20B—C21B151.2 (2)
C13A—C17A—C2OA—C21A80.6 (3)C13B—C17B—C20B—C21B89.5 (3)
O22A—C22A—O3A—C3A0.9 (5)O22B—C22B—O3B—C3B2.0 (5)
C23A—C22A—O3A—C3A177.9 (3)C23B—C22B—O3B—C3B179.9 (3)
C2A—C3A—O3A—C22A89.1 (3)C4B—C3B—O3B—C22B150.3 (2)
C4A—C3A—O3A—C22A149.6 (2)C2B—C3B—O3B—C22B87.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5A—H5A···O20Ai0.821.982.795 (2)171
O5B—H5B···O20Bii0.821.982.783 (2)165
Symmetry codes: (i) x1, y, z1; (ii) x, y, z1.

Experimental details

Crystal data
Chemical formulaC23H35ClO4
Mr410.96
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)7.6862 (6), 27.484 (2), 11.1863 (9)
β (°) 110.094 (2)
V3)2219.2 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.29 × 0.24 × 0.23
Data collection
DiffractometerBruker APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2000)
Tmin, Tmax0.895, 0.956
No. of measured, independent and
observed [I > 2σ(I)] reflections
55742, 10978, 7889
Rint0.032
(sin θ/λ)max1)0.674
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.117, 1.00
No. of reflections10978
No. of parameters515
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.26
Absolute structureFlack (1983), 5188 Friedel pairs
Absolute structure parameter0.04 (4)

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97(Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5A—H5A···O20Ai0.821.982.795 (2)171.0
O5B—H5B···O20Bii0.821.982.783 (2)164.7
Symmetry codes: (i) x1, y, z1; (ii) x, y, z1.
 

Acknowledgements

This work was supported by Fundação para a Ciência e a Tecnologia. RMAP thanks FCT for a grant (SFRH/BD/18013/2004).

References

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