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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 4| April 2012| Pages o1211-o1212
doi:10.1107/S1600536812012482

3β-Chloro-5α-cholestan-6-one

Samina Khan Yusufzai,a Hasnah Osman,a‡ Aisyah Saad Abdul Rahim,b Suhana Arshadc and Ibrahim Abdul Razakc*§

aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and cSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: arazaki@usm.my

(Received 12 March 2012; accepted 22 March 2012; online 28 March 2012)

The asymmetric unit of the title compound, C27H45ClO, consists of two crystallographically independent mol­ecules. In both mol­ecules, the three cyclo­hexane rings in the steroid fused-ring systems adopt chair conformations, while the cyclo­pentane ring adopts a half-chair conformation in one mol­ecule and an envelope conformation in the other. In the crystal, the mol­ecules are linked into a two-dimensional network by weak C—H⋯O hydrogen bonds. The crystal studied is a nonmerohedral twin with a refined ratio of twin components of 0.264 (3):0.736 (3).

Related literature

For a crystallographic comparison of cholesterols, see: Rajnikant et al. (2006[Rajnikant, Dinesh, & Bhavnaish, C. (2006). Acta Cryst. A62, 136-145.]). For the biological activity of steroidal derivatives, see: Pluempe & Pulls (1971[Pluempe, H. & Pulls, W. (1971). Chem. Abstr. 74, 1251154n.]); Sawhney et al. (1975[Sawhney, N. S., Sing, J. & Bansal, O. P. (1975). Indian Chem. Soc. 52, 561-562.]); Yonova & Stoilkova (2004[Yonova, P. A. & Stoilkova, G. M. (2004). J. Plant Growth Regul. 23, 280-291.]). For related structures, see: Yusufzai et al. (2012[Yusufzai, S. K., Osman, H., Sulaiman, O., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o473-o474.]); Ketuly et al. (2011[Ketuly, K. A., Hadi, A. H. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o773-o774.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For the synthesis, see: Windaus & Dalmer (1919[Windaus, A. & Dalmer, O. (1919). Chem. Ber. 52, 162-167.]). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data

  • C27H45ClO

  • Mr = 421.08

  • Monoclinic, P 21

  • a = 7.6603 (3) Å

  • b = 15.7249 (6) Å

  • c = 20.8434 (8) Å

  • β = 94.069 (2)°

  • V = 2504.41 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.17 mm−1

  • T = 100 K

  • 0.25 × 0.18 × 0.14 mm
Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.960, Tmax = 0.977

  • 14186 measured reflections

  • 14186 independent reflections

  • 10360 reflections with I > 2σ(I)

  • Rint = 0.000
Refinement

  • R[F2 > 2σ(F2)] = 0.067

  • wR(F2) = 0.179

  • S = 1.02

  • 14186 reflections

  • 534 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.74 e Å−3

  • Δρmin = −0.34 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 6535 Friedel pairs

  • Flack parameter: 0.03 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C7A—H7AA⋯O1Ai 0.99 2.37 3.349 (4) 168
C7B—H7BA⋯O1Bi 0.99 2.47 3.265 (4) 137
C23A—H23B⋯O1Bii 0.99 2.51 3.414 (4) 152
C23B—H23D⋯O1Aiii 0.99 2.50 3.453 (4) 161
Symmetry codes: (i) x+1, y, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+1]; (iii) [-x+1, y+{\script{1\over 2}}, -z+2].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812012482/lh5434sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012482/lh5434Isup2.hkl

checkCIF report


Comment top

The cholesterol molecule in steroidal chemistry is well known as it comprises of a four-ring structure of which three are six-membered cyclohexane rings and one is a five membered carbon ring (Rajnikant et al., 2006). The importance of steroidal compounds has long been recognized in the field of synthetic organic chemistry and steroidal derivatives are an important group of natural compounds possessing a variety of biological activities such as antidiabetic, bactericidal, fungicidal, herbicidal and algeacidal activities (Pluempe & Pulls, 1971; Sawhney et al., 1975; Yonova & Stoilkova, 2004). In the present work an attempt has been made to synthesize a derivative of the cholesterol molecule. The crystal structure of the title compound is presented herein.

The asymmetric unit of the title compound (Fig. 1), consists of two crystallographically independent molecules A and B. The bond lengths and angles are within normal ranges and are comparable to the related structures (Yusufzai et al., 2012; Ketuly et al., 2011). In molecule A, the cyclohexane (C1A–C3A/C8A/C9A/C17A, C3A–C8A & C9A–C12A/C16A/C17A) rings adopt chair conformation (Cremer & Pople, 1975) [puckering parameters Q= 0.560 (3) Å, Θ= 169.0 (3)° and Φ= 353.7 (15)°; Q= 0.571 (3) Å, Θ= 180.0 (3)° and Φ= 283.0 (17)° and Q= 0.577 (3) Å, Θ= 173.9 (3)° and Φ= 54.0 (3)°, respectively] while the cyclopentane (C12A–C16A) ring is twisted about the C16A—C12A bond [puckering parameters Q= 0.452 (3) Å and φ= 349.1 (4)°], thereby adopting a half-chair conformation. Meanwhile, in molecule B, the cyclohexane (C1B–C3B/C8B/C9B/C17B, C3B–C8B & C9B–C12B/C16B/C17B) rings adopt chair conformations [puckering parameters Q= 0.562 (3) Å, Θ= 167.4 (3)° and Φ= 352.5 (14)°; Q= 0.564 (3) Å, Θ= 178.4 (3)° and Φ= 298.0 (8)° and Q= 0.569 (3) Å, Θ= 175.7 (3)° and Φ= 52.0 (4)°, respectively] and the cyclopentane (C12B–C16B) ring is in envelope conformation with puckering parameters Q= 0.456 (3) Å and φ= 351.4 (4)° with atom C12B at the flap.

There are nine chiral centres presented in each molecule. From the structure presented, these centers exhibit the following relative chiralities: C3A/C3B = S; C5A/C5B = S; C8A/C8B = R; C9A/C9B = S; C12A/C12B = R; C13A/C13B = R; C16A/C16B = S; C17A/C17B = S and C21A/C21B = R.

The crystal packing is shown in Fig. 2. The molecules are connected by C7A—H7AA···O1Ai, C7B—H7BA···O1Bi6, C23A—H23B···O1Bii and C23B—H23D···O1Aiii intermolecular hydrogen bonds (Table 1) into a two-dimensional network parallel to ac plane.

Related literature top

For a crystallographic comparison of cholesterols, see: Rajnikant et al. (2006). For the biological activity of steroidal derivatives, see: Pluempe & Pulls (1971); Sawhney et al. (1975); Yonova & Stoilkova (2004). For related structures, see: Yusufzai et al. (2012); Ketuly et al. (2011). For ring conformations, see: Cremer & Pople (1975). For the synthesis, see: Windaus & Dalmer (1919). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Experimental top

A solution of 3β-chloro-6-nitrocholest-5-ene (12 g) and glacial acetic acid (240 ml) was heated just to get a clear solution. Then zinc dust (24 g) was added gradually in small portions with constant shaking. The suspension was heated under reflux for 4 h and water (24 ml) was added at regular intervals during the course of reaction. The hot solution was poured into ice-cold water. The organic matter was extracted with ether and ethereal solution was washed successively with water, sodium bicarbonate solution (5%) and again with water and dried over anhydrous sodium sulfate. Evaporation of the solvent furnished the ketone as an oil which was crystallized from methanol to give shiny needle like crystals, m.p.: 401-402K [reported m.p. 402K (Windaus & Dalmer, 1919)].

Refinement top

All H atoms were positioned geometrically [C–H = 0.98–1.0 Å] and refined using a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating group model was applied to the methyl groups. 6535 Friedel pairs were used to determine the absolute configuration. The crystal studied is a non-merohedral twin with the refined ratio of twin components of 0.264 (3): 0.736 (3).

Structure description top

The cholesterol molecule in steroidal chemistry is well known as it comprises of a four-ring structure of which three are six-membered cyclohexane rings and one is a five membered carbon ring (Rajnikant et al., 2006). The importance of steroidal compounds has long been recognized in the field of synthetic organic chemistry and steroidal derivatives are an important group of natural compounds possessing a variety of biological activities such as antidiabetic, bactericidal, fungicidal, herbicidal and algeacidal activities (Pluempe & Pulls, 1971; Sawhney et al., 1975; Yonova & Stoilkova, 2004). In the present work an attempt has been made to synthesize a derivative of the cholesterol molecule. The crystal structure of the title compound is presented herein.

The asymmetric unit of the title compound (Fig. 1), consists of two crystallographically independent molecules A and B. The bond lengths and angles are within normal ranges and are comparable to the related structures (Yusufzai et al., 2012; Ketuly et al., 2011). In molecule A, the cyclohexane (C1A–C3A/C8A/C9A/C17A, C3A–C8A & C9A–C12A/C16A/C17A) rings adopt chair conformation (Cremer & Pople, 1975) [puckering parameters Q= 0.560 (3) Å, Θ= 169.0 (3)° and Φ= 353.7 (15)°; Q= 0.571 (3) Å, Θ= 180.0 (3)° and Φ= 283.0 (17)° and Q= 0.577 (3) Å, Θ= 173.9 (3)° and Φ= 54.0 (3)°, respectively] while the cyclopentane (C12A–C16A) ring is twisted about the C16A—C12A bond [puckering parameters Q= 0.452 (3) Å and φ= 349.1 (4)°], thereby adopting a half-chair conformation. Meanwhile, in molecule B, the cyclohexane (C1B–C3B/C8B/C9B/C17B, C3B–C8B & C9B–C12B/C16B/C17B) rings adopt chair conformations [puckering parameters Q= 0.562 (3) Å, Θ= 167.4 (3)° and Φ= 352.5 (14)°; Q= 0.564 (3) Å, Θ= 178.4 (3)° and Φ= 298.0 (8)° and Q= 0.569 (3) Å, Θ= 175.7 (3)° and Φ= 52.0 (4)°, respectively] and the cyclopentane (C12B–C16B) ring is in envelope conformation with puckering parameters Q= 0.456 (3) Å and φ= 351.4 (4)° with atom C12B at the flap.

There are nine chiral centres presented in each molecule. From the structure presented, these centers exhibit the following relative chiralities: C3A/C3B = S; C5A/C5B = S; C8A/C8B = R; C9A/C9B = S; C12A/C12B = R; C13A/C13B = R; C16A/C16B = S; C17A/C17B = S and C21A/C21B = R.

The crystal packing is shown in Fig. 2. The molecules are connected by C7A—H7AA···O1Ai, C7B—H7BA···O1Bi6, C23A—H23B···O1Bii and C23B—H23D···O1Aiii intermolecular hydrogen bonds (Table 1) into a two-dimensional network parallel to ac plane.

For a crystallographic comparison of cholesterols, see: Rajnikant et al. (2006). For the biological activity of steroidal derivatives, see: Pluempe & Pulls (1971); Sawhney et al. (1975); Yonova & Stoilkova (2004). For related structures, see: Yusufzai et al. (2012); Ketuly et al. (2011). For ring conformations, see: Cremer & Pople (1975). For the synthesis, see: Windaus & Dalmer (1919). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound. For clarity, those H atoms not involved in the intermolecular interactions (dashed lines) have been omitted.
3β-Chloro-5α-cholestan-6-one top
Crystal data top
C27H45ClOF(000) = 928
Mr = 421.08Dx = 1.117 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5836 reflections
a = 7.6603 (3) Åθ = 2.8–30.1°
b = 15.7249 (6) ŵ = 0.17 mm−1
c = 20.8434 (8) ÅT = 100 K
β = 94.069 (2)°Block, colourless
V = 2504.41 (17) Å30.25 × 0.18 × 0.14 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		14186 independent reflections
Radiation source: fine-focus sealed tube10360 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
φ and ω scansθmax = 30.2°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −10→10
Tmin = 0.960, Tmax = 0.977k = −22→22
14186 measured reflectionsl = −21→29
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)] = 0.067H-atom parameters constrained
wR(F2) = 0.179 w = 1/[σ2(Fo2) + (0.0924P)2 + 0.2267P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
14186 reflectionsΔρmax = 0.74 e Å−3
534 parametersΔρmin = −0.34 e Å−3
1 restraintAbsolute structure: Flack (1983), 6535 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (6)
Crystal data top
C27H45ClOV = 2504.41 (17) Å3
Mr = 421.08Z = 4
Monoclinic, P21Mo Kα radiation
a = 7.6603 (3) ŵ = 0.17 mm−1
b = 15.7249 (6) ÅT = 100 K
c = 20.8434 (8) Å0.25 × 0.18 × 0.14 mm
β = 94.069 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		14186 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		10360 reflections with I > 2σ(I)
Tmin = 0.960, Tmax = 0.977Rint = 0.000
14186 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.067H-atom parameters constrained
wR(F2) = 0.179Δρmax = 0.74 e Å−3
S = 1.02Δρmin = −0.34 e Å−3
14186 reflectionsAbsolute structure: Flack (1983), 6535 Friedel pairs
534 parametersAbsolute structure parameter: 0.03 (6)
1 restraint
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1A0.95587 (11)0.43447 (6)1.15732 (3)0.0373 (2)
O1A0.5385 (3)0.36817 (15)0.94654 (11)0.0309 (5)
C1A0.6511 (3)0.43069 (19)0.85333 (13)0.0217 (5)
H1AA0.62730.49230.84810.026*
H1AB0.55370.39950.83020.026*
C2A0.6558 (3)0.40841 (18)0.92389 (13)0.0213 (5)
C3A0.8149 (3)0.43897 (19)0.96392 (13)0.0207 (5)
H3AA0.81740.50220.95930.025*
C4A0.8036 (4)0.4207 (2)1.03561 (13)0.0246 (6)
H4AA0.69650.44701.05080.030*
H4AB0.79750.35861.04280.030*
C5A0.9647 (4)0.4573 (2)1.07281 (13)0.0257 (6)
H5AA0.96360.52041.06710.031*
C6A1.1334 (4)0.4230 (2)1.04917 (13)0.0281 (7)
H6AA1.14040.36091.05700.034*
H6AB1.23440.45021.07330.034*
C7A1.1416 (4)0.4408 (2)0.97677 (13)0.0268 (6)
H7AA1.25040.41570.96210.032*
H7AB1.14710.50300.97000.032*
C8A0.9838 (3)0.40478 (18)0.93530 (13)0.0194 (6)
C9A0.9845 (3)0.43831 (19)0.86532 (12)0.0194 (5)
H9AA0.97570.50160.86830.023*
C10A1.1523 (4)0.4202 (2)0.83238 (13)0.0242 (6)
H10A1.17090.35790.83140.029*
H10B1.25220.44560.85840.029*
C11A1.1515 (3)0.4548 (2)0.76347 (13)0.0226 (6)
H11A1.15270.51770.76480.027*
H11B1.25910.43580.74410.027*
C12A0.9914 (3)0.42491 (18)0.72111 (13)0.0185 (5)
C13A0.9501 (4)0.47380 (18)0.65620 (13)0.0194 (5)
H13A0.97150.53550.66520.023*
C14A0.7497 (4)0.46238 (19)0.64270 (13)0.0231 (6)
H14A0.72480.41710.61030.028*
H14B0.69590.51600.62600.028*
C15A0.6741 (3)0.4377 (2)0.70748 (12)0.0225 (5)
H15A0.57540.47530.71690.027*
H15B0.63340.37790.70680.027*
C16A0.8290 (3)0.45001 (17)0.75665 (12)0.0183 (5)
H16A0.83840.51270.76430.022*
C17A0.8228 (3)0.40925 (17)0.82266 (12)0.0174 (5)
H17A0.82930.34610.81740.021*
C18A0.9882 (4)0.3067 (2)0.93698 (15)0.0277 (6)
H18A1.09480.28650.91860.042*
H18B0.88550.28430.91180.042*
H18C0.98710.28720.98160.042*
C19A0.9991 (4)0.32876 (18)0.70822 (15)0.0244 (6)
H19A1.00500.29800.74920.037*
H19B1.10310.31570.68530.037*
H19C0.89400.31130.68200.037*
C20A1.2515 (4)0.45940 (19)0.61080 (13)0.0240 (6)
H20A1.30920.45180.57070.036*
H20B1.29350.41600.64190.036*
H20C1.27880.51600.62840.036*
C21A1.0524 (4)0.45052 (18)0.59722 (13)0.0217 (5)
H21A1.02660.38970.58620.026*
C22A0.9858 (4)0.50540 (19)0.53937 (13)0.0229 (6)
H22A0.85820.49630.53160.027*
H22B1.00400.56600.55090.027*
C23A1.0721 (4)0.48833 (19)0.47650 (13)0.0242 (6)
H23A1.19650.50590.48150.029*
H23B1.06840.42660.46720.029*
C24A0.9802 (4)0.53656 (19)0.41997 (15)0.0261 (6)
H24A0.85750.51660.41430.031*
H24B0.97760.59770.43110.031*
C25A1.0634 (4)0.5272 (2)0.35591 (14)0.0281 (6)
H25A1.19070.54110.36320.034*
C26A1.0478 (5)0.4370 (2)0.33031 (15)0.0381 (8)
H26A1.09450.39720.36340.057*
H26B1.11420.43170.29200.057*
H26C0.92440.42380.31900.057*
C27A0.9819 (6)0.5897 (2)0.30635 (17)0.0430 (9)
H27A1.00200.64800.32170.064*
H27B0.85570.57910.30010.064*
H27C1.03550.58210.26540.064*
Cl1B0.48971 (13)0.70424 (7)0.33925 (4)0.0439 (2)
O1B0.0567 (3)0.78060 (15)0.52100 (10)0.0317 (5)
C1B0.1591 (3)0.72188 (18)0.62247 (13)0.0208 (5)
H1BA0.13330.66060.62750.025*
H1BB0.06090.75440.63880.025*
C2B0.1684 (4)0.74109 (18)0.55219 (14)0.0221 (6)
C3B0.3314 (3)0.7090 (2)0.52305 (13)0.0222 (5)
H3BA0.33390.64600.52970.027*
C4B0.3277 (4)0.7235 (2)0.45059 (14)0.0268 (6)
H4BA0.22290.69590.42920.032*
H4BB0.32110.78520.44130.032*
C5B0.4905 (4)0.6868 (2)0.42489 (14)0.0308 (7)
H5BA0.49090.62410.43280.037*
C6B0.6570 (4)0.7241 (2)0.45813 (15)0.0347 (8)
H6BA0.66270.78580.44890.042*
H6BB0.76060.69660.44130.042*
C7B0.6589 (4)0.7099 (2)0.53135 (14)0.0290 (7)
H7BA0.76430.73760.55230.035*
H7BB0.66800.64820.54020.035*
C8B0.4956 (4)0.74503 (19)0.56156 (14)0.0221 (6)
C9B0.4919 (3)0.71337 (19)0.63200 (13)0.0216 (6)
H9BA0.48210.65000.62930.026*
C10B0.6575 (3)0.7313 (2)0.67522 (14)0.0262 (6)
H10C0.67680.79350.67720.031*
H10D0.75880.70550.65560.031*
C11B0.6503 (4)0.6971 (2)0.74369 (14)0.0261 (6)
H11C0.75690.71530.76970.031*
H11D0.64970.63420.74240.031*
C12B0.4889 (4)0.72799 (18)0.77626 (14)0.0215 (6)
C13B0.4411 (4)0.68052 (18)0.83786 (13)0.0216 (6)
H13B0.45610.61840.82940.026*
C14B0.2412 (4)0.6963 (2)0.83999 (13)0.0244 (6)
H14C0.18240.64460.85480.029*
H14D0.21940.74350.86980.029*
C15B0.1708 (4)0.71938 (19)0.77054 (13)0.0235 (6)
H15C0.07180.68210.75580.028*
H15D0.13200.77940.76780.028*
C16B0.3282 (3)0.70463 (18)0.73089 (13)0.0196 (5)
H16B0.33480.64170.72450.024*
C17B0.3284 (3)0.74356 (18)0.66389 (13)0.0191 (5)
H17B0.33530.80680.66870.023*
C18B0.4960 (4)0.8432 (2)0.55865 (15)0.0295 (7)
H18D0.59770.86510.58470.044*
H18E0.38850.86510.57550.044*
H18F0.50200.86160.51390.044*
C19B0.5012 (4)0.82440 (19)0.78917 (15)0.0265 (6)
H19D0.60300.83620.81900.040*
H19E0.39470.84380.80810.040*
H19F0.51380.85450.74860.040*
C20B0.7436 (4)0.6881 (2)0.89911 (14)0.0269 (6)
H20D0.78860.73110.87060.040*
H20E0.76720.63130.88250.040*
H20F0.80140.69440.94230.040*
C21B0.5456 (4)0.6999 (2)0.90218 (13)0.0246 (6)
H21B0.52400.76070.91330.030*
C22B0.4755 (4)0.6440 (2)0.95550 (14)0.0251 (6)
H22C0.34820.65430.95650.030*
H22D0.49130.58360.94390.030*
C23B0.5618 (4)0.6585 (2)1.02329 (14)0.0287 (7)
H23C0.68440.63831.02490.034*
H23D0.56380.72021.03280.034*
C24B0.4650 (5)0.6122 (2)1.07447 (14)0.0302 (7)
H24C0.45070.55181.06160.036*
H24D0.34650.63711.07550.036*
C25B0.5553 (5)0.6157 (2)1.14292 (16)0.0365 (8)
H25B0.67790.59441.14110.044*
C26B0.5628 (6)0.7051 (3)1.16937 (17)0.0534 (11)
H26D0.62420.74191.14050.080*
H26E0.62540.70501.21200.080*
H26F0.44360.72631.17280.080*
C27B0.4601 (7)0.5578 (3)1.18807 (19)0.0580 (13)
H27D0.52120.55891.23100.087*
H27E0.45830.49951.17140.087*
H27F0.33980.57801.19070.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl1A0.0440 (4)0.0481 (5)0.0199 (3)−0.0101 (4)0.0024 (3)0.0046 (3)
O1A0.0234 (10)0.0345 (12)0.0354 (12)−0.0065 (9)0.0053 (9)0.0060 (10)
C1A0.0146 (11)0.0246 (14)0.0259 (13)0.0015 (11)0.0011 (9)0.0000 (12)
C2A0.0166 (12)0.0205 (13)0.0273 (14)0.0028 (10)0.0034 (10)0.0006 (11)
C3A0.0212 (12)0.0173 (13)0.0239 (13)0.0019 (11)0.0031 (10)0.0034 (11)
C4A0.0274 (14)0.0250 (16)0.0216 (13)−0.0011 (12)0.0035 (10)0.0016 (11)
C5A0.0319 (15)0.0252 (16)0.0200 (13)−0.0048 (12)0.0026 (11)0.0028 (11)
C6A0.0267 (14)0.0394 (19)0.0178 (13)−0.0039 (14)−0.0021 (10)0.0076 (13)
C7A0.0205 (13)0.0388 (18)0.0208 (13)−0.0023 (13)0.0002 (10)0.0045 (13)
C8A0.0176 (12)0.0204 (14)0.0200 (13)−0.0008 (10)0.0005 (10)0.0026 (10)
C9A0.0172 (11)0.0225 (14)0.0181 (12)−0.0011 (11)−0.0010 (9)0.0020 (11)
C10A0.0199 (13)0.0332 (17)0.0191 (13)0.0020 (12)−0.0021 (10)0.0009 (12)
C11A0.0181 (12)0.0290 (16)0.0209 (13)0.0008 (11)0.0016 (10)0.0000 (11)
C12A0.0182 (12)0.0164 (13)0.0207 (12)0.0012 (10)0.0001 (9)0.0004 (10)
C13A0.0224 (13)0.0172 (13)0.0181 (12)0.0014 (10)−0.0027 (10)−0.0002 (10)
C14A0.0213 (13)0.0246 (15)0.0228 (13)−0.0010 (11)−0.0026 (10)−0.0009 (11)
C15A0.0200 (12)0.0246 (14)0.0224 (12)0.0012 (12)−0.0019 (10)0.0005 (11)
C16A0.0209 (12)0.0171 (13)0.0168 (11)0.0017 (10)0.0010 (9)0.0005 (10)
C17A0.0153 (11)0.0153 (12)0.0217 (13)0.0003 (9)0.0014 (9)0.0002 (10)
C18A0.0323 (16)0.0240 (16)0.0268 (15)0.0067 (12)0.0016 (12)0.0036 (12)
C19A0.0296 (15)0.0165 (14)0.0274 (15)0.0029 (11)0.0031 (11)−0.0011 (11)
C20A0.0273 (14)0.0244 (14)0.0206 (12)0.0035 (12)0.0033 (11)−0.0010 (11)
C21A0.0240 (13)0.0184 (14)0.0228 (13)−0.0009 (11)0.0008 (10)−0.0023 (11)
C22A0.0234 (14)0.0220 (15)0.0226 (14)0.0025 (11)−0.0027 (11)−0.0030 (11)
C23A0.0302 (15)0.0225 (15)0.0199 (13)0.0018 (12)0.0025 (11)−0.0001 (11)
C24A0.0341 (16)0.0190 (14)0.0248 (15)0.0034 (12)−0.0001 (12)0.0024 (11)
C25A0.0387 (17)0.0258 (15)0.0199 (13)−0.0024 (13)0.0030 (12)0.0006 (11)
C26A0.058 (2)0.0294 (18)0.0263 (15)0.0085 (17)0.0001 (14)0.0005 (14)
C27A0.071 (3)0.0285 (18)0.0296 (18)0.0049 (18)0.0075 (17)0.0050 (14)
Cl1B0.0535 (5)0.0531 (6)0.0259 (4)0.0118 (5)0.0082 (3)0.0052 (4)
O1B0.0227 (10)0.0377 (13)0.0343 (12)0.0052 (10)−0.0006 (9)0.0068 (10)
C1B0.0143 (12)0.0191 (14)0.0290 (14)0.0005 (10)0.0009 (10)−0.0004 (11)
C2B0.0179 (12)0.0193 (13)0.0287 (14)−0.0021 (11)−0.0009 (10)−0.0009 (11)
C3B0.0205 (12)0.0191 (14)0.0269 (14)−0.0008 (11)0.0006 (10)0.0012 (12)
C4B0.0247 (14)0.0267 (16)0.0288 (15)0.0016 (12)0.0000 (11)0.0023 (12)
C5B0.0380 (17)0.0318 (17)0.0230 (14)0.0086 (14)0.0065 (12)0.0055 (13)
C6B0.0270 (15)0.044 (2)0.0341 (17)0.0089 (14)0.0107 (13)0.0086 (15)
C7B0.0196 (13)0.0380 (18)0.0296 (15)0.0026 (13)0.0036 (11)0.0057 (14)
C8B0.0164 (12)0.0223 (14)0.0278 (15)0.0011 (11)0.0018 (10)0.0040 (12)
C9B0.0155 (12)0.0193 (14)0.0299 (15)−0.0012 (10)0.0006 (10)−0.0009 (12)
C10B0.0127 (12)0.0359 (18)0.0300 (15)−0.0024 (11)0.0022 (10)0.0025 (13)
C11B0.0179 (12)0.0279 (16)0.0324 (15)0.0025 (12)0.0001 (11)0.0005 (13)
C12B0.0205 (13)0.0193 (14)0.0247 (14)−0.0006 (10)0.0022 (10)−0.0001 (11)
C13B0.0233 (13)0.0170 (13)0.0245 (13)−0.0011 (11)0.0014 (10)−0.0039 (11)
C14B0.0207 (13)0.0258 (15)0.0270 (14)−0.0014 (12)0.0025 (10)−0.0014 (12)
C15B0.0197 (13)0.0233 (15)0.0278 (14)0.0007 (11)0.0034 (10)−0.0025 (11)
C16B0.0163 (12)0.0178 (13)0.0249 (13)−0.0003 (11)0.0012 (9)−0.0013 (11)
C17B0.0145 (11)0.0181 (13)0.0246 (13)0.0002 (10)0.0002 (10)−0.0016 (11)
C18B0.0288 (15)0.0231 (16)0.0362 (17)−0.0059 (12)0.0003 (13)0.0070 (13)
C19B0.0264 (14)0.0200 (14)0.0323 (16)−0.0036 (11)−0.0033 (12)−0.0015 (12)
C20B0.0249 (14)0.0268 (15)0.0282 (14)−0.0038 (12)−0.0029 (11)−0.0012 (12)
C21B0.0251 (14)0.0197 (14)0.0283 (14)0.0001 (12)−0.0025 (11)−0.0033 (12)
C22B0.0302 (15)0.0207 (15)0.0241 (14)−0.0014 (12)−0.0003 (11)−0.0015 (12)
C23B0.0342 (17)0.0252 (16)0.0268 (15)0.0019 (13)0.0023 (12)−0.0033 (12)
C24B0.0440 (19)0.0231 (16)0.0232 (15)−0.0032 (13)−0.0005 (13)−0.0012 (12)
C25B0.044 (2)0.0359 (19)0.0290 (16)−0.0013 (16)0.0009 (14)0.0014 (14)
C26B0.087 (3)0.048 (2)0.0254 (17)−0.032 (2)0.0062 (18)−0.0002 (17)
C27B0.104 (4)0.036 (2)0.032 (2)−0.020 (2)−0.004 (2)0.0072 (16)
Geometric parameters (Å, º) top
Cl1A—C5A1.804 (3)Cl1B—C5B1.805 (3)
O1A—C2A1.221 (3)O1B—C2B1.209 (3)
C1A—C2A1.510 (4)C1B—C2B1.502 (4)
C1A—C17A1.540 (4)C1B—C17B1.544 (4)
C1A—H1AA0.9900C1B—H1BA0.9900
C1A—H1AB0.9900C1B—H1BB0.9900
C2A—C3A1.506 (4)C2B—C3B1.513 (4)
C3A—C4A1.530 (4)C3B—C4B1.526 (4)
C3A—C8A1.558 (4)C3B—C8B1.551 (4)
C3A—H3AA1.0000C3B—H3BA1.0000
C4A—C5A1.523 (4)C4B—C5B1.507 (4)
C4A—H4AA0.9900C4B—H4BA0.9900
C4A—H4AB0.9900C4B—H4BB0.9900
C5A—C6A1.515 (4)C5B—C6B1.525 (5)
C5A—H5AA1.0000C5B—H5BA1.0000
C6A—C7A1.540 (4)C6B—C7B1.541 (4)
C6A—H6AA0.9900C6B—H6BA0.9900
C6A—H6AB0.9900C6B—H6BB0.9900
C7A—C8A1.542 (4)C7B—C8B1.542 (4)
C7A—H7AA0.9900C7B—H7BA0.9900
C7A—H7AB0.9900C7B—H7BB0.9900
C8A—C18A1.542 (4)C8B—C18B1.545 (4)
C8A—C9A1.551 (4)C8B—C9B1.552 (4)
C9A—C10A1.526 (4)C9B—C10B1.529 (4)
C9A—C17A1.542 (4)C9B—C17B1.534 (4)
C9A—H9AA1.0000C9B—H9BA1.0000
C10A—C11A1.535 (4)C10B—C11B1.530 (4)
C10A—H10A0.9900C10B—H10C0.9900
C10A—H10B0.9900C10B—H10D0.9900
C11A—C12A1.533 (4)C11B—C12B1.531 (4)
C11A—H11A0.9900C11B—H11C0.9900
C11A—H11B0.9900C11B—H11D0.9900
C12A—C19A1.538 (4)C12B—C19B1.541 (4)
C12A—C16A1.544 (4)C12B—C16B1.542 (4)
C12A—C13A1.569 (4)C12B—C13B1.551 (4)
C13A—C21A1.548 (4)C13B—C21B1.542 (4)
C13A—C14A1.552 (4)C13B—C14B1.555 (4)
C13A—H13A1.0000C13B—H13B1.0000
C14A—C15A1.555 (4)C14B—C15B1.551 (4)
C14A—H14A0.9900C14B—H14C0.9900
C14A—H14B0.9900C14B—H14D0.9900
C15A—C16A1.524 (4)C15B—C16B1.527 (4)
C15A—H15A0.9900C15B—H15C0.9900
C15A—H15B0.9900C15B—H15D0.9900
C16A—C17A1.522 (4)C16B—C17B1.525 (4)
C16A—H16A1.0000C16B—H16B1.0000
C17A—H17A1.0000C17B—H17B1.0000
C18A—H18A0.9800C18B—H18D0.9800
C18A—H18B0.9800C18B—H18E0.9800
C18A—H18C0.9800C18B—H18F0.9800
C19A—H19A0.9800C19B—H19D0.9800
C19A—H19B0.9800C19B—H19E0.9800
C19A—H19C0.9800C19B—H19F0.9800
C20A—C21A1.538 (4)C20B—C21B1.534 (4)
C20A—H20A0.9800C20B—H20D0.9800
C20A—H20B0.9800C20B—H20E0.9800
C20A—H20C0.9800C20B—H20F0.9800
C21A—C22A1.540 (4)C21B—C22B1.543 (4)
C21A—H21A1.0000C21B—H21B1.0000
C22A—C23A1.533 (4)C22B—C23B1.534 (4)
C22A—H22A0.9900C22B—H22C0.9900
C22A—H22B0.9900C22B—H22D0.9900
C23A—C24A1.530 (4)C23B—C24B1.527 (4)
C23A—H23A0.9900C23B—H23C0.9900
C23A—H23B0.9900C23B—H23D0.9900
C24A—C25A1.527 (4)C24B—C25B1.542 (5)
C24A—H24A0.9900C24B—H24C0.9900
C24A—H24B0.9900C24B—H24D0.9900
C25A—C26A1.517 (5)C25B—C26B1.509 (6)
C25A—C27A1.527 (5)C25B—C27B1.531 (5)
C25A—H25A1.0000C25B—H25B1.0000
C26A—H26A0.9800C26B—H26D0.9800
C26A—H26B0.9800C26B—H26E0.9800
C26A—H26C0.9800C26B—H26F0.9800
C27A—H27A0.9800C27B—H27D0.9800
C27A—H27B0.9800C27B—H27E0.9800
C27A—H27C0.9800C27B—H27F0.9800
C2A—C1A—C17A113.1 (2)C2B—C1B—C17B113.9 (2)
C2A—C1A—H1AA109.0C2B—C1B—H1BA108.8
C17A—C1A—H1AA109.0C17B—C1B—H1BA108.8
C2A—C1A—H1AB109.0C2B—C1B—H1BB108.8
C17A—C1A—H1AB109.0C17B—C1B—H1BB108.8
H1AA—C1A—H1AB107.8H1BA—C1B—H1BB107.7
O1A—C2A—C3A122.7 (3)O1B—C2B—C1B123.2 (3)
O1A—C2A—C1A122.0 (3)O1B—C2B—C3B121.9 (3)
C3A—C2A—C1A115.3 (2)C1B—C2B—C3B114.9 (2)
C2A—C3A—C4A112.4 (2)C2B—C3B—C4B112.9 (2)
C2A—C3A—C8A109.8 (2)C2B—C3B—C8B109.4 (2)
C4A—C3A—C8A114.6 (2)C4B—C3B—C8B114.5 (2)
C2A—C3A—H3AA106.5C2B—C3B—H3BA106.5
C4A—C3A—H3AA106.5C4B—C3B—H3BA106.5
C8A—C3A—H3AA106.5C8B—C3B—H3BA106.5
C5A—C4A—C3A109.1 (2)C5B—C4B—C3B109.7 (2)
C5A—C4A—H4AA109.9C5B—C4B—H4BA109.7
C3A—C4A—H4AA109.9C3B—C4B—H4BA109.7
C5A—C4A—H4AB109.9C5B—C4B—H4BB109.7
C3A—C4A—H4AB109.9C3B—C4B—H4BB109.7
H4AA—C4A—H4AB108.3H4BA—C4B—H4BB108.2
C6A—C5A—C4A112.3 (3)C4B—C5B—C6B112.2 (3)
C6A—C5A—Cl1A109.8 (2)C4B—C5B—Cl1B110.4 (2)
C4A—C5A—Cl1A109.7 (2)C6B—C5B—Cl1B109.6 (2)
C6A—C5A—H5AA108.3C4B—C5B—H5BA108.2
C4A—C5A—H5AA108.3C6B—C5B—H5BA108.2
Cl1A—C5A—H5AA108.3Cl1B—C5B—H5BA108.2
C5A—C6A—C7A110.4 (2)C5B—C6B—C7B110.1 (3)
C5A—C6A—H6AA109.6C5B—C6B—H6BA109.6
C7A—C6A—H6AA109.6C7B—C6B—H6BA109.6
C5A—C6A—H6AB109.6C5B—C6B—H6BB109.6
C7A—C6A—H6AB109.6C7B—C6B—H6BB109.6
H6AA—C6A—H6AB108.1H6BA—C6B—H6BB108.2
C6A—C7A—C8A113.4 (2)C6B—C7B—C8B113.7 (2)
C6A—C7A—H7AA108.9C6B—C7B—H7BA108.8
C8A—C7A—H7AA108.9C8B—C7B—H7BA108.8
C6A—C7A—H7AB108.9C6B—C7B—H7BB108.8
C8A—C7A—H7AB108.9C8B—C7B—H7BB108.8
H7AA—C7A—H7AB107.7H7BA—C7B—H7BB107.7
C18A—C8A—C7A109.9 (2)C7B—C8B—C18B109.7 (3)
C18A—C8A—C9A111.1 (2)C7B—C8B—C3B108.0 (2)
C7A—C8A—C9A110.3 (2)C18B—C8B—C3B110.4 (2)
C18A—C8A—C3A110.7 (2)C7B—C8B—C9B110.0 (2)
C7A—C8A—C3A107.3 (2)C18B—C8B—C9B111.0 (3)
C9A—C8A—C3A107.5 (2)C3B—C8B—C9B107.7 (2)
C10A—C9A—C17A110.7 (2)C10B—C9B—C17B110.9 (2)
C10A—C9A—C8A114.7 (2)C10B—C9B—C8B115.3 (2)
C17A—C9A—C8A112.7 (2)C17B—C9B—C8B112.4 (2)
C10A—C9A—H9AA106.0C10B—C9B—H9BA105.8
C17A—C9A—H9AA106.0C17B—C9B—H9BA105.8
C8A—C9A—H9AA106.0C8B—C9B—H9BA105.8
C9A—C10A—C11A114.0 (2)C9B—C10B—C11B113.7 (2)
C9A—C10A—H10A108.7C9B—C10B—H10C108.8
C11A—C10A—H10A108.7C11B—C10B—H10C108.8
C9A—C10A—H10B108.7C9B—C10B—H10D108.8
C11A—C10A—H10B108.7C11B—C10B—H10D108.8
H10A—C10A—H10B107.6H10C—C10B—H10D107.7
C12A—C11A—C10A112.4 (2)C10B—C11B—C12B112.7 (2)
C12A—C11A—H11A109.1C10B—C11B—H11C109.1
C10A—C11A—H11A109.1C12B—C11B—H11C109.1
C12A—C11A—H11B109.1C10B—C11B—H11D109.1
C10A—C11A—H11B109.1C12B—C11B—H11D109.1
H11A—C11A—H11B107.9H11C—C11B—H11D107.8
C11A—C12A—C19A111.3 (2)C11B—C12B—C19B110.3 (2)
C11A—C12A—C16A106.5 (2)C11B—C12B—C16B106.7 (2)
C19A—C12A—C16A112.2 (2)C19B—C12B—C16B112.2 (2)
C11A—C12A—C13A116.8 (2)C11B—C12B—C13B117.4 (2)
C19A—C12A—C13A109.8 (2)C19B—C12B—C13B110.1 (2)
C16A—C12A—C13A99.7 (2)C16B—C12B—C13B99.7 (2)
C21A—C13A—C14A112.3 (2)C21B—C13B—C12B119.1 (2)
C21A—C13A—C12A119.1 (2)C21B—C13B—C14B113.3 (2)
C14A—C13A—C12A103.7 (2)C12B—C13B—C14B103.7 (2)
C21A—C13A—H13A107.1C21B—C13B—H13B106.7
C14A—C13A—H13A107.1C12B—C13B—H13B106.7
C12A—C13A—H13A107.1C14B—C13B—H13B106.7
C13A—C14A—C15A107.2 (2)C15B—C14B—C13B106.8 (2)
C13A—C14A—H14A110.3C15B—C14B—H14C110.4
C15A—C14A—H14A110.3C13B—C14B—H14C110.4
C13A—C14A—H14B110.3C15B—C14B—H14D110.4
C15A—C14A—H14B110.3C13B—C14B—H14D110.4
H14A—C14A—H14B108.5H14C—C14B—H14D108.6
C16A—C15A—C14A103.4 (2)C16B—C15B—C14B103.5 (2)
C16A—C15A—H15A111.1C16B—C15B—H15C111.1
C14A—C15A—H15A111.1C14B—C15B—H15C111.1
C16A—C15A—H15B111.1C16B—C15B—H15D111.1
C14A—C15A—H15B111.1C14B—C15B—H15D111.1
H15A—C15A—H15B109.0H15C—C15B—H15D109.0
C17A—C16A—C15A118.8 (2)C17B—C16B—C15B119.1 (2)
C17A—C16A—C12A113.8 (2)C17B—C16B—C12B114.4 (2)
C15A—C16A—C12A105.1 (2)C15B—C16B—C12B105.0 (2)
C17A—C16A—H16A106.1C17B—C16B—H16B105.8
C15A—C16A—H16A106.1C15B—C16B—H16B105.8
C12A—C16A—H16A106.1C12B—C16B—H16B105.8
C16A—C17A—C1A111.4 (2)C16B—C17B—C9B109.1 (2)
C16A—C17A—C9A108.7 (2)C16B—C17B—C1B111.6 (2)
C1A—C17A—C9A111.7 (2)C9B—C17B—C1B111.6 (2)
C16A—C17A—H17A108.3C16B—C17B—H17B108.2
C1A—C17A—H17A108.3C9B—C17B—H17B108.2
C9A—C17A—H17A108.3C1B—C17B—H17B108.2
C8A—C18A—H18A109.5C8B—C18B—H18D109.5
C8A—C18A—H18B109.5C8B—C18B—H18E109.5
H18A—C18A—H18B109.5H18D—C18B—H18E109.5
C8A—C18A—H18C109.5C8B—C18B—H18F109.5
H18A—C18A—H18C109.5H18D—C18B—H18F109.5
H18B—C18A—H18C109.5H18E—C18B—H18F109.5
C12A—C19A—H19A109.5C12B—C19B—H19D109.5
C12A—C19A—H19B109.5C12B—C19B—H19E109.5
H19A—C19A—H19B109.5H19D—C19B—H19E109.5
C12A—C19A—H19C109.5C12B—C19B—H19F109.5
H19A—C19A—H19C109.5H19D—C19B—H19F109.5
H19B—C19A—H19C109.5H19E—C19B—H19F109.5
C21A—C20A—H20A109.5C21B—C20B—H20D109.5
C21A—C20A—H20B109.5C21B—C20B—H20E109.5
H20A—C20A—H20B109.5H20D—C20B—H20E109.5
C21A—C20A—H20C109.5C21B—C20B—H20F109.5
H20A—C20A—H20C109.5H20D—C20B—H20F109.5
H20B—C20A—H20C109.5H20E—C20B—H20F109.5
C20A—C21A—C22A111.2 (2)C20B—C21B—C13B113.2 (2)
C20A—C21A—C13A112.6 (2)C20B—C21B—C22B110.9 (2)
C22A—C21A—C13A109.3 (2)C13B—C21B—C22B109.1 (2)
C20A—C21A—H21A107.8C20B—C21B—H21B107.8
C22A—C21A—H21A107.8C13B—C21B—H21B107.8
C13A—C21A—H21A107.8C22B—C21B—H21B107.8
C23A—C22A—C21A115.6 (2)C23B—C22B—C21B115.4 (3)
C23A—C22A—H22A108.4C23B—C22B—H22C108.4
C21A—C22A—H22A108.4C21B—C22B—H22C108.4
C23A—C22A—H22B108.4C23B—C22B—H22D108.4
C21A—C22A—H22B108.4C21B—C22B—H22D108.4
H22A—C22A—H22B107.4H22C—C22B—H22D107.5
C24A—C23A—C22A111.6 (2)C24B—C23B—C22B111.9 (3)
C24A—C23A—H23A109.3C24B—C23B—H23C109.2
C22A—C23A—H23A109.3C22B—C23B—H23C109.2
C24A—C23A—H23B109.3C24B—C23B—H23D109.2
C22A—C23A—H23B109.3C22B—C23B—H23D109.2
H23A—C23A—H23B108.0H23C—C23B—H23D107.9
C25A—C24A—C23A115.3 (3)C23B—C24B—C25B114.9 (3)
C25A—C24A—H24A108.4C23B—C24B—H24C108.5
C23A—C24A—H24A108.4C25B—C24B—H24C108.5
C25A—C24A—H24B108.4C23B—C24B—H24D108.5
C23A—C24A—H24B108.4C25B—C24B—H24D108.5
H24A—C24A—H24B107.5H24C—C24B—H24D107.5
C26A—C25A—C24A111.7 (3)C26B—C25B—C27B109.7 (3)
C26A—C25A—C27A110.2 (3)C26B—C25B—C24B112.0 (3)
C24A—C25A—C27A110.7 (3)C27B—C25B—C24B110.2 (3)
C26A—C25A—H25A108.0C26B—C25B—H25B108.3
C24A—C25A—H25A108.0C27B—C25B—H25B108.3
C27A—C25A—H25A108.0C24B—C25B—H25B108.3
C25A—C26A—H26A109.5C25B—C26B—H26D109.5
C25A—C26A—H26B109.5C25B—C26B—H26E109.5
H26A—C26A—H26B109.5H26D—C26B—H26E109.5
C25A—C26A—H26C109.5C25B—C26B—H26F109.5
H26A—C26A—H26C109.5H26D—C26B—H26F109.5
H26B—C26A—H26C109.5H26E—C26B—H26F109.5
C25A—C27A—H27A109.5C25B—C27B—H27D109.5
C25A—C27A—H27B109.5C25B—C27B—H27E109.5
H27A—C27A—H27B109.5H27D—C27B—H27E109.5
C25A—C27A—H27C109.5C25B—C27B—H27F109.5
H27A—C27A—H27C109.5H27D—C27B—H27F109.5
H27B—C27A—H27C109.5H27E—C27B—H27F109.5
C17A—C1A—C2A—O1A−131.1 (3)C17B—C1B—C2B—O1B−130.8 (3)
C17A—C1A—C2A—C3A48.7 (3)C17B—C1B—C2B—C3B47.8 (3)
O1A—C2A—C3A—C4A−5.1 (4)O1B—C2B—C3B—C4B−6.2 (4)
C1A—C2A—C3A—C4A175.2 (2)C1B—C2B—C3B—C4B175.2 (2)
O1A—C2A—C3A—C8A123.7 (3)O1B—C2B—C3B—C8B122.7 (3)
C1A—C2A—C3A—C8A−56.0 (3)C1B—C2B—C3B—C8B−56.0 (3)
C2A—C3A—C4A—C5A−177.3 (2)C2B—C3B—C4B—C5B−177.8 (3)
C8A—C3A—C4A—C5A56.4 (3)C8B—C3B—C4B—C5B56.1 (3)
C3A—C4A—C5A—C6A−56.4 (3)C3B—C4B—C5B—C6B−56.9 (4)
C3A—C4A—C5A—Cl1A−178.8 (2)C3B—C4B—C5B—Cl1B−179.5 (2)
C4A—C5A—C6A—C7A56.8 (4)C4B—C5B—C6B—C7B56.8 (4)
Cl1A—C5A—C6A—C7A179.2 (2)Cl1B—C5B—C6B—C7B179.8 (2)
C5A—C6A—C7A—C8A−56.2 (4)C5B—C6B—C7B—C8B−55.2 (4)
C6A—C7A—C8A—C18A−67.0 (3)C6B—C7B—C8B—C18B−68.3 (4)
C6A—C7A—C8A—C9A170.2 (3)C6B—C7B—C8B—C3B52.1 (4)
C6A—C7A—C8A—C3A53.4 (3)C6B—C7B—C8B—C9B169.4 (3)
C2A—C3A—C8A—C18A−62.2 (3)C2B—C3B—C8B—C7B179.1 (2)
C4A—C3A—C8A—C18A65.4 (3)C4B—C3B—C8B—C7B−53.0 (3)
C2A—C3A—C8A—C7A178.0 (2)C2B—C3B—C8B—C18B−60.9 (3)
C4A—C3A—C8A—C7A−54.4 (3)C4B—C3B—C8B—C18B67.0 (3)
C2A—C3A—C8A—C9A59.3 (3)C2B—C3B—C8B—C9B60.3 (3)
C4A—C3A—C8A—C9A−173.1 (2)C4B—C3B—C8B—C9B−171.7 (2)
C18A—C8A—C9A—C10A−66.0 (3)C7B—C8B—C9B—C10B53.7 (3)
C7A—C8A—C9A—C10A56.0 (3)C18B—C8B—C9B—C10B−67.9 (3)
C3A—C8A—C9A—C10A172.7 (2)C3B—C8B—C9B—C10B171.2 (2)
C18A—C8A—C9A—C17A61.8 (3)C7B—C8B—C9B—C17B−177.9 (2)
C7A—C8A—C9A—C17A−176.1 (2)C18B—C8B—C9B—C17B60.5 (3)
C3A—C8A—C9A—C17A−59.4 (3)C3B—C8B—C9B—C17B−60.4 (3)
C17A—C9A—C10A—C11A51.8 (3)C17B—C9B—C10B—C11B52.3 (3)
C8A—C9A—C10A—C11A−179.3 (2)C8B—C9B—C10B—C11B−178.5 (3)
C9A—C10A—C11A—C12A−53.4 (3)C9B—C10B—C11B—C12B−53.9 (4)
C10A—C11A—C12A—C19A−68.2 (3)C10B—C11B—C12B—C19B−68.1 (3)
C10A—C11A—C12A—C16A54.3 (3)C10B—C11B—C12B—C16B54.0 (3)
C10A—C11A—C12A—C13A164.6 (2)C10B—C11B—C12B—C13B164.7 (2)
C11A—C12A—C13A—C21A81.2 (3)C11B—C12B—C13B—C21B78.0 (3)
C19A—C12A—C13A—C21A−46.7 (3)C19B—C12B—C13B—C21B−49.3 (3)
C16A—C12A—C13A—C21A−164.6 (2)C16B—C12B—C13B—C21B−167.4 (2)
C11A—C12A—C13A—C14A−153.2 (2)C11B—C12B—C13B—C14B−155.0 (2)
C19A—C12A—C13A—C14A78.9 (3)C19B—C12B—C13B—C14B77.6 (3)
C16A—C12A—C13A—C14A−39.0 (3)C16B—C12B—C13B—C14B−40.4 (3)
C21A—C13A—C14A—C15A149.2 (2)C21B—C13B—C14B—C15B151.8 (2)
C12A—C13A—C14A—C15A19.3 (3)C12B—C13B—C14B—C15B21.3 (3)
C13A—C14A—C15A—C16A8.7 (3)C13B—C14B—C15B—C16B6.9 (3)
C14A—C15A—C16A—C17A−163.1 (2)C14B—C15B—C16B—C17B−162.9 (2)
C14A—C15A—C16A—C12A−34.3 (3)C14B—C15B—C16B—C12B−33.2 (3)
C11A—C12A—C16A—C17A−60.5 (3)C11B—C12B—C16B—C17B−58.9 (3)
C19A—C12A—C16A—C17A61.5 (3)C19B—C12B—C16B—C17B62.1 (3)
C13A—C12A—C16A—C17A177.6 (2)C13B—C12B—C16B—C17B178.6 (2)
C11A—C12A—C16A—C15A167.8 (2)C11B—C12B—C16B—C15B168.7 (2)
C19A—C12A—C16A—C15A−70.2 (3)C19B—C12B—C16B—C15B−70.4 (3)
C13A—C12A—C16A—C15A46.0 (3)C13B—C12B—C16B—C15B46.1 (3)
C15A—C16A—C17A—C1A−50.7 (3)C15B—C16B—C17B—C9B−175.1 (2)
C12A—C16A—C17A—C1A−175.3 (2)C12B—C16B—C17B—C9B59.6 (3)
C15A—C16A—C17A—C9A−174.3 (2)C15B—C16B—C17B—C1B−51.4 (3)
C12A—C16A—C17A—C9A61.1 (3)C12B—C16B—C17B—C1B−176.7 (2)
C2A—C1A—C17A—C16A−167.2 (2)C10B—C9B—C17B—C16B−53.4 (3)
C2A—C1A—C17A—C9A−45.4 (3)C8B—C9B—C17B—C16B175.9 (2)
C10A—C9A—C17A—C16A−53.8 (3)C10B—C9B—C17B—C1B−177.1 (2)
C8A—C9A—C17A—C16A176.2 (2)C8B—C9B—C17B—C1B52.2 (3)
C10A—C9A—C17A—C1A−177.3 (2)C2B—C1B—C17B—C16B−166.8 (2)
C8A—C9A—C17A—C1A52.8 (3)C2B—C1B—C17B—C9B−44.5 (3)
C14A—C13A—C21A—C20A−178.5 (2)C12B—C13B—C21B—C20B−55.1 (4)
C12A—C13A—C21A—C20A−57.1 (3)C14B—C13B—C21B—C20B−177.4 (3)
C14A—C13A—C21A—C22A57.3 (3)C12B—C13B—C21B—C22B−179.1 (2)
C12A—C13A—C21A—C22A178.7 (2)C14B—C13B—C21B—C22B58.6 (3)
C20A—C21A—C22A—C23A56.4 (3)C20B—C21B—C22B—C23B57.0 (3)
C13A—C21A—C22A—C23A−178.7 (2)C13B—C21B—C22B—C23B−177.7 (2)
C21A—C22A—C23A—C24A172.0 (2)C21B—C22B—C23B—C24B170.3 (3)
C22A—C23A—C24A—C25A176.8 (3)C22B—C23B—C24B—C25B173.6 (3)
C23A—C24A—C25A—C26A66.8 (4)C23B—C24B—C25B—C26B65.1 (4)
C23A—C24A—C25A—C27A−169.9 (3)C23B—C24B—C25B—C27B−172.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7A—H7AA···O1Ai0.992.373.349 (4)168
C7B—H7BA···O1Bi0.992.473.265 (4)137
C23A—H23B···O1Bii0.992.513.414 (4)152
C23B—H23D···O1Aiii0.992.503.453 (4)161
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1; (iii) −x+1, y+1/2, −z+2.

Experimental details

Crystal data
Chemical formulaC27H45ClO
Mr421.08
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)7.6603 (3), 15.7249 (6), 20.8434 (8)
β (°) 94.069 (2)
V (Å3)2504.41 (17)
Z4
Radiation typeMo Kα
µ (mm−1)0.17
Crystal size (mm)0.25 × 0.18 × 0.14
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.960, 0.977
No. of measured, independent and
observed [I > 2σ(I)] reflections		14186, 14186, 10360
Rint0.000
(sin θ/λ)max (Å−1)0.708
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.179, 1.02
No. of reflections14186
No. of parameters534
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.74, −0.34
Absolute structureFlack (1983), 6535 Friedel pairs
Absolute structure parameter0.03 (6)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7A—H7AA···O1Ai0.99002.37003.349 (4)168.00
C7B—H7BA···O1Bi0.99002.47003.265 (4)137.00
C23A—H23B···O1Bii0.99002.51003.414 (4)152.00
C23B—H23D···O1Aiii0.99002.50003.453 (4)161.00
Symmetry codes: (i) x+1, y, z; (ii) −x+1, y−1/2, −z+1; (iii) −x+1, y+1/2, −z+2.
 

Footnotes

‡Additional correspondence author, e-mail: ohasnah@usm.my.

§Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the FRGS grant (No. 203/PKIMIA/6711179), MOSTI grant No. 09-05-lfn-meb-004 and Research University grant No.1001/PFIZIK/811151 to conduct this work. SKY thanks USM for providing Graduate Assistance financial support.

References

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ISSN: 2056-9890
Volume 68| Part 4| April 2012| Pages o1211-o1212
doi:10.1107/S1600536812012482
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