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

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ISSN: 2056-9890

4,10,16,22-Tetra­kis(2-chloro­acet­­oxy)-6,12,18,24-tetra­meth­­oxy-2,8,14,20-tetra­pentyl­resorcin[4]arene

aSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
*Correspondence e-mail: maguireg@ukzn.ac.za

(Received 16 September 2011; accepted 23 September 2011; online 12 October 2011)

The title compound, C60H76Cl4O12, has a macrocyclic structure and both the upper and lower rim have disordered atoms. There are no hydrogen bonds or ππ stacking inter­actions in the crystal.

Related literature

For applications of resorcin[4]arenes, see: Asadi et al. (2011[Asadi, A., Ajami, D. & Rebek, J. Jr (2011). J. Am. Chem. Soc. 133, 10682-10684.]); Yong et al. (2010[Yong, Y., Yan, S., Ying, H. & Chaoguo, Y. (2010). Chin. J. Chem. 28, 705-712.]); Balasubramanian et al. (2007[Balasubramanian, R., Kwon, Y. & Wei, A. (2007). J. Mater. Chem. 17, 105-112.]); Misra & Liu (2007[Misra, T. K. & Liu, C. (2007). J. Colloid Interface Sci. 310, 178-183.]); Dickert et al. (1997[Dickert, F. L., Balumler, U. P. A. & Stathopulos, H. (1997). Anal. Chem. 69, 1000-1005.]). For structural information, see: Wiegmann & Mattay (2011[Wiegmann, S. & Mattay, J. (2011). Org. Lett. 13, 3226-3228.]). For the synthesis of tetra­meth­oxy resorcin[4]arene, see: McIldowie et al. (2000[McIldowie, M. J., Mocerino, M., Skelton, B. W. & White, A. H. (2000). Org. Lett. 2, 3869-3871.]).

[Scheme 1]

Experimental

Crystal data
  • C60H76Cl4O12

  • Mr = 1131.01

  • Monoclinic, P 21 /n

  • a = 12.4190 (5) Å

  • b = 26.1925 (11) Å

  • c = 19.1638 (8) Å

  • β = 107.407 (1)°

  • V = 5948.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 173 K

  • 0.22 × 0.18 × 0.16 mm

Data collection
  • Bruker Kappa DUO APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.945, Tmax = 0.960

  • 37389 measured reflections

  • 13698 independent reflections

  • 8473 reflections with I > 2σ(I)

  • Rint = 0.037

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.199

  • S = 1.05

  • 13698 reflections

  • 694 parameters

  • 12 restraints

  • H-atom parameters constrained

  • Δρmax = 0.61 e Å−3

  • Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Over recent decades interest in resorcin[4]arenes has grown. They are ideal macrocyclic molecules with versatile applications such as hosts for molecular recognition (Asadi et al., 2011), catalysts (Yong et al., 2010), functionalization into nanoparticle scaffolds (Balasubramanian et al., 2007), multidentate ligands (Misra & Liu 2007), and analytical reagents (Dickert et al., 1997).

A wide range of resorcin[4]arene derivatives with different physicochemical properties have thus been synthesized. One family of these molecules which has received much attention recently is the semi flexible tetramethoxy resorcin[4]arenes (Wiegmann et al., 2011). Here we report the crystal structure of novel a tetramethoxy resorcin[4]arene derivative containing chloroacetoxy moieties on the upper rim.

The title compound has a rccc (boat) configuration (Fig. 1). The structure posseses disorder in both the upper and lower rim regions. In the crystal the molecule forms capsule structures due to interlocking between two molecules by way of the chloroacetoxy "head groups" (Fig. 2). The feet are such that two adjacent pentyl groups are linear, while the remaining two are bent. This may be due to interdigitation of a chlorine atom in between the "feet" (Fig. 3). This results in insufficient space for the remaining pairs of alkyl groups to extend in a linear fashion. There are no hydrogen bonds or π-π stacking interactions in the crystal.

Related literature top

For applications of resorcin[4]arenes, see: Asadi et al. (2011); Yong et al. (2010); Balasubramanian et al. (2007); Misra & Liu (2007); Dickert et al. (1997). For structural information, see: Wiegmann & Mattay (2011). For the synthesis of tetramethoxy resorcin[4]arene, see: McIldowie et al. (2000).

Experimental top

2,8,14,20-Tetrapentyl-4,10,16,22-tetrakis (2-chloroacetoxy)-6,12,18,24-tetramethoxyresorcin[4]arene

Tetramethoxy resorcin[4]arene (0.825 g, 1 mmol) (McIldowie et al. (2000)) and pyridine (0.363 g, 8 mmol) were added in tetrahydrofuran (20 ml) followed by the addition of chloroacetyl chloride (0.903 g, 8 mmol). The solution was stirred at room temperature for 24 h. Subsequently, methylene chloride (20 ml) was added and then the solvent was removed under vacuum at 60°C. Water and methylene chloride was then added to the residue. The organic layer was washed with water, dried over anhydrous magnesium sulfate and then removed under reduced presssure. The residue was then stirred in methanol, filtered and washed with methanol to give pure product (Yield: 0.90 g, 80%).

Crystals suitable for single-crystal X-ray diffraction were grown in methanol:methylene chloride(1:2) at room temperature. M.p. = 464 K.

Refinement top

All non-hydrogen atoms, except some of the disordered moieties, were refined anisotropically. The disordered moieties are Cl1A and C31A versus Cl1B and C31B with site occupancy factors of 0.50 each; C35A and C36A versus C35B and C36B with site occupancy factors of 0.689 and 0.311 respectively; C44A versus C44B with site occupancy factors of 0.472 and 0.528 respectively; C50A, C51A and C52A versus C50B, C51B and C52B with site occupancy factors of 0.450 and 0.550 respectively. All these disordered atoms except Cl1A, Cl1B, C31A and C31B, were refined with isotropic temperature factors. C36A, C36B, C44A, C44B, C52A and C52B were refined with fixed Uiso value. All the hydrogen atoms were placed at calculated positions with bond distances to their parent atoms ranging from 0.95 Å to 1.00 Å and refined as riding on their parent atoms with Uiso (H) = 1.2 or 1.5 Ueq (C).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with selected atomic numbering; the H atoms have been omitted for clarity. Displacement ellipsoids are drawn at 40% probability.
[Figure 2] Fig. 2. The capsule formation by two "bowl" structures. Hydrogen atoms in each unit have been omitted. Displacement ellipsoids are drawn at 40% probability.
[Figure 3] Fig. 3. Packing of the title compound in the crystal. The interlocking of "head groups" as well as interdigitation of one of the chlorines in the "feet" is visible. All H atoms have been omitted for clarity.
4,10,16,22-Tetrakis(2-chloroacetoxy)-6,12,18,24-tetramethoxy- 2,8,14,20-tetrapentylresorcin[4]arene top
Crystal data top
C60H76Cl4O12F(000) = 2400
Mr = 1131.01Dx = 1.263 Mg m3
Monoclinic, P21/nMelting point: 464 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 12.4190 (5) ÅCell parameters from 37389 reflections
b = 26.1925 (11) Åθ = 1.6–27.6°
c = 19.1638 (8) ŵ = 0.26 mm1
β = 107.407 (1)°T = 173 K
V = 5948.2 (4) Å3Block, colourless
Z = 40.22 × 0.18 × 0.16 mm
Data collection top
Bruker Kappa DUO APEXII
diffractometer
13698 independent reflections
Radiation source: fine-focus sealed tube8473 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
0.5° ϕ scans and ωθmax = 27.6°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
h = 1615
Tmin = 0.945, Tmax = 0.960k = 2634
37389 measured reflectionsl = 2424
Refinement top
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) = 0.199H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0967P)2 + 2.9849P]
where P = (Fo2 + 2Fc2)/3
13698 reflections(Δ/σ)max = 0.001
694 parametersΔρmax = 0.61 e Å3
12 restraintsΔρmin = 0.60 e Å3
Crystal data top
C60H76Cl4O12V = 5948.2 (4) Å3
Mr = 1131.01Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.4190 (5) ŵ = 0.26 mm1
b = 26.1925 (11) ÅT = 173 K
c = 19.1638 (8) Å0.22 × 0.18 × 0.16 mm
β = 107.407 (1)°
Data collection top
Bruker Kappa DUO APEXII
diffractometer
13698 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
8473 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.960Rint = 0.037
37389 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06312 restraints
wR(F2) = 0.199H-atom parameters constrained
S = 1.05Δρmax = 0.61 e Å3
13698 reflectionsΔρmin = 0.60 e Å3
694 parameters
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*/UeqOcc. (<1)
Cl20.37232 (8)1.17006 (3)0.77801 (6)0.0613 (3)
Cl31.02976 (8)0.94705 (5)0.71176 (7)0.0896 (4)
Cl40.89879 (7)0.69935 (3)1.22023 (5)0.0568 (2)
O10.58385 (17)0.71264 (8)1.08755 (11)0.0447 (5)
O20.22948 (15)0.80022 (9)1.04907 (11)0.0467 (5)
O30.3177 (2)0.83760 (11)1.15675 (14)0.0655 (7)
O40.28349 (16)0.92378 (8)1.02051 (10)0.0383 (4)
O50.42609 (14)1.04324 (7)0.87884 (10)0.0343 (4)
O60.25737 (18)1.07961 (8)0.82508 (15)0.0590 (6)
O70.48893 (17)1.06167 (8)0.72073 (12)0.0435 (5)
O80.83894 (15)0.97054 (8)0.75480 (11)0.0404 (5)
O90.91678 (18)1.02505 (10)0.84722 (13)0.0604 (7)
O100.88876 (17)0.91723 (8)0.92280 (12)0.0495 (5)
O110.75973 (16)0.80334 (7)1.07790 (10)0.0399 (5)
O120.8927 (2)0.74518 (10)1.07721 (13)0.0610 (7)
C10.5166 (2)0.76784 (10)0.98675 (14)0.0329 (6)
C20.5025 (2)0.74646 (10)1.05024 (14)0.0341 (6)
C30.4093 (2)0.75906 (11)1.07244 (15)0.0366 (6)
H30.40000.74491.11590.044*
C40.3301 (2)0.79262 (11)1.03034 (15)0.0353 (6)
C50.3388 (2)0.81517 (10)0.96691 (14)0.0303 (5)
C60.4356 (2)0.80219 (10)0.94770 (14)0.0310 (5)
H60.44650.81780.90560.037*
C70.2476 (2)0.84855 (10)0.91776 (13)0.0298 (5)
H70.19090.85500.94440.036*
C80.29357 (19)0.90037 (10)0.90445 (13)0.0273 (5)
C90.31071 (19)0.93773 (10)0.95898 (13)0.0294 (5)
C100.3523 (2)0.98547 (10)0.94921 (14)0.0320 (6)
H100.36421.01080.98630.038*
C110.37592 (19)0.99554 (10)0.88454 (14)0.0291 (5)
C120.35850 (19)0.96081 (10)0.82739 (13)0.0277 (5)
C130.31784 (19)0.91312 (10)0.84009 (13)0.0281 (5)
H130.30600.88800.80290.034*
C140.38146 (19)0.97586 (10)0.75646 (13)0.0294 (5)
H140.35201.01130.74430.035*
C150.5075 (2)0.97705 (10)0.76416 (13)0.0289 (5)
C160.5570 (2)1.02006 (10)0.74239 (14)0.0327 (6)
C170.6695 (2)1.01844 (11)0.74282 (14)0.0355 (6)
H170.70411.04760.72920.043*
C180.7296 (2)0.97399 (11)0.76317 (14)0.0340 (6)
C190.6851 (2)0.93042 (11)0.78424 (14)0.0320 (6)
C200.5727 (2)0.93388 (10)0.78544 (14)0.0300 (5)
H200.54020.90510.80170.036*
C210.7459 (2)0.87911 (11)0.79701 (16)0.0369 (6)
H210.82630.88600.79960.044*
C220.7473 (2)0.85710 (11)0.87009 (15)0.0354 (6)
C230.8220 (2)0.87808 (11)0.93367 (16)0.0384 (6)
C240.8252 (2)0.86028 (11)1.00241 (16)0.0403 (6)
H240.87380.87551.04540.048*
C250.7559 (2)0.81987 (11)1.00677 (15)0.0356 (6)
C260.6820 (2)0.79624 (10)0.94673 (15)0.0338 (6)
C270.6791 (2)0.81638 (11)0.87832 (15)0.0349 (6)
H270.62860.80170.83570.042*
C280.6123 (2)0.75094 (10)0.95753 (15)0.0360 (6)
H280.66360.72920.99640.043*
C290.5627 (3)0.68305 (14)1.14442 (19)0.0573 (9)
H29A0.55750.70571.18400.086*
H29B0.62450.65871.16330.086*
H29C0.49160.66441.12510.086*
C300.2355 (3)0.82100 (14)1.11442 (18)0.0504 (8)
C320.1851 (2)0.82006 (10)0.84650 (14)0.0341 (6)
H32A0.13450.84430.81240.041*
H32B0.24110.80760.82300.041*
C330.1157 (2)0.77491 (11)0.85916 (17)0.0403 (6)
H33A0.16460.75270.89750.048*
H33B0.09020.75460.81360.048*
C370.2840 (2)0.96274 (13)1.07281 (16)0.0439 (7)
H37A0.36080.97601.09330.066*
H37B0.25790.94841.11220.066*
H37C0.23370.99051.04880.066*
C380.3572 (2)1.08245 (11)0.84892 (16)0.0391 (6)
C390.4290 (3)1.12970 (11)0.85365 (19)0.0468 (7)
H39A0.50651.11960.85530.056*
H39B0.43321.14840.89930.056*
C400.3215 (2)0.94171 (11)0.69113 (14)0.0366 (6)
H40A0.35090.90650.70130.044*
H40B0.23990.94080.68640.044*
C410.3361 (3)0.95917 (16)0.61902 (17)0.0570 (9)
H41A0.30390.99390.60780.068*
H41B0.41770.96130.62420.068*
C420.2804 (4)0.9242 (2)0.55562 (19)0.0794 (13)
H42A0.30220.88870.57140.095*
H42B0.19770.92680.54610.095*
C450.5285 (3)1.10133 (12)0.6836 (2)0.0541 (8)
H45A0.59441.11780.71760.081*
H45B0.46861.12670.66540.081*
H45C0.54971.08680.64250.081*
C460.9241 (2)0.99649 (13)0.80048 (17)0.0460 (7)
C471.0362 (3)0.98543 (17)0.7874 (2)0.0659 (11)
H47A1.08610.96860.83160.079*
H47B1.07161.01830.78140.079*
C480.6976 (3)0.84422 (13)0.73124 (17)0.0483 (7)
H48A0.61610.83900.72420.058*
H48B0.73510.81050.74120.058*
C530.9810 (3)0.93181 (15)0.9826 (2)0.0713 (12)
H53A0.95320.94641.02110.107*
H53B1.02630.95730.96660.107*
H53C1.02770.90181.00170.107*
C540.8348 (2)0.76581 (11)1.10790 (16)0.0402 (6)
C550.8325 (3)0.75687 (12)1.18448 (16)0.0448 (7)
H55A0.75310.75611.18520.054*
H55B0.87090.78551.21580.054*
C560.5662 (3)0.71637 (12)0.88991 (17)0.0447 (7)
H56A0.51330.73620.85030.054*
H56B0.62940.70490.87230.054*
C570.5046 (3)0.66932 (13)0.9078 (2)0.0606 (9)
H57A0.55560.65190.95100.073*
H57B0.43780.68120.92130.073*
C580.4657 (4)0.63036 (15)0.8457 (2)0.0718 (11)
H58A0.53290.61500.83630.086*
H58B0.42200.64830.80060.086*
C590.3923 (4)0.58741 (17)0.8626 (3)0.0835 (13)
H59A0.32470.60300.87120.100*
H59B0.36610.56510.81910.100*
C600.4499 (5)0.5553 (2)0.9268 (4)0.117 (2)
H60A0.51980.54150.92060.176*
H60B0.40020.52710.93090.176*
H60C0.46770.57600.97130.176*
Cl1A0.0878 (2)0.84469 (12)1.18840 (16)0.0715 (7)0.50
C31A0.1126 (9)0.8071 (3)1.1188 (6)0.044 (2)0.50
H31A0.10850.77041.13000.053*0.50
H31B0.05530.81441.07140.053*0.50
C34A0.0121 (3)0.79050 (14)0.8823 (2)0.0607 (11)0.689 (6)
H34A0.03980.81000.84170.073*0.689 (6)
H34B0.03730.81380.92470.073*0.689 (6)
C35A0.0552 (5)0.7461 (2)0.9031 (4)0.0659 (16)*0.689 (6)
H35A0.10540.75910.93060.079*0.689 (6)
H35B0.00330.72050.93350.079*0.689 (6)
C36A0.1256 (6)0.7222 (3)0.8289 (4)0.090*0.689 (6)
H36A0.17040.69360.83830.135*0.689 (6)
H36B0.07450.70970.80240.135*0.689 (6)
H36C0.17610.74810.79950.135*0.689 (6)
C43A0.3050 (6)0.9326 (3)0.4853 (4)0.127 (2)*0.472 (7)
H43A0.38560.94160.49540.153*0.472 (7)
H43B0.25950.96180.45940.153*0.472 (7)
C44A0.2794 (12)0.8865 (5)0.4370 (8)0.127 (2)*0.472 (7)
H44A0.29760.89360.39160.191*0.472 (7)
H44B0.19900.87820.42550.191*0.472 (7)
H44C0.32460.85760.46230.191*0.472 (7)
C49A0.7135 (4)0.86634 (16)0.6609 (2)0.0706 (12)0.450 (6)
H49A0.66390.89650.64550.085*0.450 (6)
H49B0.79260.87780.67060.085*0.450 (6)
C50A0.6871 (10)0.8288 (4)0.6016 (5)0.067 (3)*0.450 (6)
H50A0.60660.81900.58960.081*0.450 (6)
H50B0.73310.79770.61820.081*0.450 (6)
C51A0.7109 (10)0.8501 (4)0.5314 (6)0.081 (3)*0.450 (6)
H51A0.67300.82740.49010.097*0.450 (6)
H51B0.79310.84760.53870.097*0.450 (6)
C52A0.6735 (10)0.9066 (4)0.5080 (6)0.090*0.450 (6)
H52A0.69420.91530.46390.135*0.450 (6)
H52B0.71150.93000.54760.135*0.450 (6)
H52C0.59160.90970.49780.135*0.450 (6)
Cl1B0.1283 (3)0.83185 (18)1.21844 (16)0.0998 (12)0.50
C31B0.1278 (9)0.8330 (5)1.1283 (6)0.064 (3)0.50
H31C0.07030.80851.10050.076*0.50
H31D0.10360.86751.10830.076*0.50
C34B0.0121 (3)0.79050 (14)0.8823 (2)0.0607 (11)0.311 (6)
H34C0.02590.82030.85360.073*0.311 (6)
H34D0.03460.79950.93480.073*0.311 (6)
C35B0.0698 (9)0.7420 (4)0.8665 (7)0.048 (3)*0.311 (6)
H35C0.14850.75320.85970.057*0.311 (6)
H35D0.06700.72500.82100.057*0.311 (6)
C36B0.0356 (13)0.7063 (6)0.9274 (8)0.090*0.311 (6)
H36D0.08640.67680.91730.135*0.311 (6)
H36E0.03910.72320.97220.135*0.311 (6)
H36F0.04180.69490.93350.135*0.311 (6)
C43B0.3050 (6)0.9326 (3)0.4853 (4)0.127 (2)*0.528 (7)
H43C0.38440.92280.49200.153*0.528 (7)
H43D0.25670.90930.44840.153*0.528 (7)
C44B0.2891 (8)0.9820 (3)0.4571 (5)0.090*0.528 (7)
H44D0.30930.98330.41140.135*0.528 (7)
H44E0.33701.00570.49250.135*0.528 (7)
H44F0.20980.99180.44740.135*0.528 (7)
C49B0.7135 (4)0.86634 (16)0.6609 (2)0.0706 (12)0.550 (6)
H49C0.79470.86510.66480.085*0.550 (6)
H49D0.69050.90270.65700.085*0.550 (6)
C50B0.6468 (8)0.8387 (3)0.5899 (4)0.071 (2)*0.550 (6)
H50C0.56970.83200.59260.085*0.550 (6)
H50D0.68300.80520.58860.085*0.550 (6)
C51B0.6360 (7)0.8667 (4)0.5159 (5)0.084 (3)*0.550 (6)
H51C0.59160.84550.47450.101*0.550 (6)
H51D0.59630.89960.51450.101*0.550 (6)
C52B0.7524 (7)0.8760 (4)0.5091 (5)0.090*0.550 (6)
H52D0.74600.89370.46300.135*0.550 (6)
H52E0.79080.84320.50980.135*0.550 (6)
H52F0.79590.89700.55010.135*0.550 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl20.0748 (6)0.0417 (4)0.0787 (6)0.0165 (4)0.0400 (5)0.0154 (4)
Cl30.0458 (5)0.1302 (10)0.1032 (9)0.0045 (6)0.0382 (5)0.0416 (8)
Cl40.0657 (5)0.0534 (5)0.0494 (5)0.0192 (4)0.0145 (4)0.0145 (4)
O10.0448 (11)0.0461 (12)0.0439 (12)0.0083 (9)0.0140 (9)0.0151 (9)
O20.0321 (9)0.0751 (15)0.0379 (11)0.0007 (10)0.0183 (8)0.0154 (10)
O30.0650 (16)0.0857 (19)0.0567 (16)0.0063 (14)0.0347 (13)0.0134 (13)
O40.0454 (10)0.0477 (11)0.0271 (10)0.0056 (9)0.0191 (8)0.0060 (8)
O50.0323 (9)0.0290 (9)0.0427 (11)0.0035 (8)0.0129 (8)0.0016 (8)
O60.0375 (12)0.0437 (13)0.0898 (19)0.0023 (10)0.0099 (11)0.0081 (12)
O70.0477 (11)0.0374 (11)0.0523 (13)0.0020 (9)0.0253 (10)0.0121 (9)
O80.0304 (9)0.0561 (12)0.0397 (11)0.0098 (9)0.0179 (8)0.0037 (9)
O90.0424 (12)0.0867 (18)0.0546 (14)0.0171 (12)0.0182 (11)0.0215 (13)
O100.0383 (11)0.0534 (13)0.0516 (13)0.0091 (10)0.0055 (9)0.0080 (10)
O110.0391 (10)0.0455 (11)0.0353 (11)0.0107 (9)0.0115 (8)0.0063 (9)
O120.0608 (14)0.0762 (17)0.0515 (14)0.0352 (13)0.0251 (11)0.0118 (12)
C10.0355 (13)0.0339 (14)0.0308 (14)0.0045 (11)0.0119 (11)0.0017 (11)
C20.0355 (13)0.0352 (14)0.0296 (14)0.0012 (11)0.0068 (10)0.0063 (11)
C30.0362 (13)0.0446 (16)0.0305 (14)0.0062 (12)0.0120 (11)0.0069 (12)
C40.0299 (12)0.0458 (16)0.0331 (14)0.0067 (12)0.0139 (11)0.0024 (12)
C50.0309 (12)0.0321 (13)0.0290 (13)0.0050 (10)0.0105 (10)0.0006 (10)
C60.0328 (12)0.0330 (14)0.0297 (13)0.0032 (11)0.0133 (10)0.0015 (11)
C70.0295 (12)0.0355 (14)0.0271 (13)0.0035 (11)0.0127 (10)0.0021 (10)
C80.0246 (11)0.0329 (13)0.0257 (12)0.0012 (10)0.0094 (9)0.0014 (10)
C90.0261 (11)0.0380 (14)0.0259 (13)0.0002 (10)0.0108 (9)0.0018 (10)
C100.0298 (12)0.0356 (14)0.0317 (14)0.0009 (11)0.0107 (10)0.0091 (11)
C110.0254 (11)0.0280 (13)0.0349 (14)0.0020 (10)0.0104 (10)0.0019 (10)
C120.0245 (11)0.0348 (13)0.0255 (12)0.0018 (10)0.0100 (9)0.0010 (10)
C130.0272 (11)0.0322 (13)0.0271 (13)0.0013 (10)0.0114 (10)0.0048 (10)
C140.0282 (12)0.0328 (13)0.0287 (13)0.0006 (10)0.0109 (10)0.0037 (10)
C150.0294 (12)0.0364 (14)0.0223 (12)0.0026 (11)0.0099 (9)0.0005 (10)
C160.0376 (13)0.0365 (14)0.0259 (13)0.0020 (11)0.0124 (10)0.0017 (11)
C170.0385 (14)0.0411 (15)0.0299 (14)0.0098 (12)0.0146 (11)0.0002 (11)
C180.0276 (12)0.0501 (16)0.0273 (13)0.0076 (12)0.0130 (10)0.0027 (12)
C190.0283 (12)0.0442 (15)0.0254 (13)0.0014 (11)0.0108 (10)0.0005 (11)
C200.0259 (11)0.0374 (14)0.0282 (13)0.0065 (11)0.0106 (10)0.0008 (11)
C210.0276 (12)0.0442 (16)0.0439 (16)0.0013 (11)0.0185 (11)0.0017 (13)
C220.0291 (12)0.0408 (15)0.0395 (15)0.0087 (11)0.0153 (11)0.0051 (12)
C230.0303 (13)0.0391 (15)0.0452 (17)0.0020 (12)0.0105 (12)0.0061 (13)
C240.0329 (13)0.0423 (16)0.0414 (16)0.0036 (12)0.0043 (12)0.0008 (13)
C250.0321 (13)0.0390 (15)0.0364 (15)0.0111 (11)0.0113 (11)0.0055 (12)
C260.0289 (12)0.0354 (14)0.0396 (15)0.0073 (11)0.0141 (11)0.0030 (12)
C270.0299 (12)0.0388 (15)0.0386 (15)0.0037 (11)0.0142 (11)0.0027 (12)
C280.0380 (13)0.0356 (14)0.0373 (15)0.0054 (12)0.0156 (11)0.0052 (12)
C290.060 (2)0.063 (2)0.048 (2)0.0076 (17)0.0150 (16)0.0269 (17)
C300.0481 (17)0.071 (2)0.0404 (18)0.0142 (17)0.0257 (15)0.0192 (16)
C320.0334 (13)0.0366 (14)0.0320 (14)0.0037 (11)0.0093 (11)0.0028 (11)
C330.0373 (14)0.0352 (15)0.0464 (17)0.0051 (12)0.0095 (12)0.0010 (12)
C370.0422 (15)0.0614 (19)0.0323 (15)0.0027 (14)0.0178 (12)0.0134 (14)
C380.0394 (15)0.0352 (15)0.0447 (17)0.0004 (12)0.0155 (12)0.0013 (12)
C390.0533 (17)0.0290 (15)0.061 (2)0.0003 (13)0.0213 (15)0.0009 (13)
C400.0287 (12)0.0514 (17)0.0303 (14)0.0019 (12)0.0099 (10)0.0004 (12)
C410.0470 (17)0.093 (3)0.0306 (16)0.0171 (18)0.0107 (13)0.0028 (16)
C420.080 (3)0.128 (4)0.0312 (19)0.032 (3)0.0188 (18)0.018 (2)
C450.072 (2)0.0436 (18)0.056 (2)0.0009 (16)0.0337 (18)0.0136 (15)
C460.0342 (14)0.064 (2)0.0407 (17)0.0113 (14)0.0133 (12)0.0002 (15)
C470.0348 (16)0.098 (3)0.070 (2)0.0168 (18)0.0225 (16)0.017 (2)
C480.0555 (18)0.0491 (18)0.0482 (18)0.0004 (15)0.0275 (15)0.0046 (14)
C530.064 (2)0.059 (2)0.069 (3)0.0237 (19)0.0126 (19)0.0152 (19)
C540.0352 (14)0.0433 (16)0.0398 (16)0.0067 (12)0.0075 (12)0.0014 (13)
C550.0470 (16)0.0475 (17)0.0371 (16)0.0128 (14)0.0084 (13)0.0033 (13)
C560.0552 (17)0.0404 (16)0.0435 (17)0.0006 (14)0.0225 (14)0.0029 (13)
C570.087 (3)0.0431 (19)0.056 (2)0.0094 (18)0.0287 (19)0.0064 (16)
C580.098 (3)0.058 (2)0.060 (2)0.009 (2)0.025 (2)0.0034 (19)
C590.105 (3)0.062 (3)0.072 (3)0.023 (2)0.009 (2)0.001 (2)
C600.108 (4)0.088 (4)0.134 (5)0.027 (3)0.003 (4)0.031 (3)
Cl1A0.0656 (16)0.0933 (18)0.0697 (19)0.0057 (13)0.0418 (13)0.0174 (15)
C31A0.040 (4)0.056 (5)0.045 (4)0.001 (4)0.026 (3)0.006 (4)
C34A0.0429 (17)0.051 (2)0.093 (3)0.0074 (15)0.0276 (18)0.0000 (19)
C49A0.097 (3)0.073 (3)0.054 (2)0.022 (2)0.040 (2)0.0134 (19)
Cl1B0.082 (2)0.180 (4)0.0565 (17)0.013 (2)0.0493 (15)0.0147 (18)
C31B0.041 (4)0.114 (9)0.041 (5)0.006 (6)0.020 (4)0.010 (6)
C34B0.0429 (17)0.051 (2)0.093 (3)0.0074 (15)0.0276 (18)0.0000 (19)
C49B0.097 (3)0.073 (3)0.054 (2)0.022 (2)0.040 (2)0.0134 (19)
Geometric parameters (Å, º) top
Cl2—C391.762 (3)C40—H40A0.9900
Cl3—C471.747 (4)C40—H40B0.9900
Cl4—C551.755 (3)C41—C421.514 (5)
O1—C21.373 (3)C41—H41A0.9900
O1—C291.424 (4)C41—H41B0.9900
O2—C301.347 (4)C42—C43A1.484 (8)
O2—C41.413 (3)C42—H42A0.9900
O3—C301.181 (4)C42—H42B0.9900
O4—C91.370 (3)C45—H45A0.9800
O4—C371.429 (3)C45—H45B0.9800
O5—C381.349 (3)C45—H45C0.9800
O5—C111.415 (3)C46—C471.514 (4)
O6—C381.189 (3)C47—H47A0.9900
O7—C161.366 (3)C47—H47B0.9900
O7—C451.427 (3)C48—C49A1.534 (5)
O8—C461.339 (4)C48—H48A0.9900
O8—C181.418 (3)C48—H48B0.9900
O9—C461.191 (4)C53—H53A0.9800
O10—C231.373 (3)C53—H53B0.9800
O10—C531.409 (4)C53—H53C0.9800
O11—C541.358 (3)C54—C551.495 (4)
O11—C251.417 (3)C55—H55A0.9900
O12—C541.187 (3)C55—H55B0.9900
C1—C61.389 (4)C56—C571.542 (5)
C1—C21.397 (4)C56—H56A0.9900
C1—C281.523 (4)C56—H56B0.9900
C2—C31.387 (4)C57—C581.532 (5)
C3—C41.385 (4)C57—H57A0.9900
C3—H30.9500C57—H57B0.9900
C4—C51.385 (4)C58—C591.543 (6)
C5—C61.400 (3)C58—H58A0.9900
C5—C71.516 (4)C58—H58B0.9900
C6—H60.9500C59—C601.486 (7)
C7—C81.524 (3)C59—H59A0.9900
C7—C321.546 (4)C59—H59B0.9900
C7—H71.0000C60—H60A0.9800
C8—C131.395 (3)C60—H60B0.9800
C8—C91.401 (3)C60—H60C0.9800
C9—C101.387 (4)Cl1A—C31A1.758 (9)
C10—C111.382 (3)C31A—H31A0.9900
C10—H100.9500C31A—H31B0.9900
C11—C121.390 (3)C34A—C35A1.552 (7)
C12—C131.396 (3)C34A—H34A0.9900
C12—C141.522 (3)C34A—H34B0.9900
C13—H130.9500C35A—C36A1.561 (9)
C14—C151.527 (3)C35A—H35A0.9900
C14—C401.538 (4)C35A—H35B0.9900
C14—H141.0000C36A—H36A0.9800
C15—C201.380 (4)C36A—H36B0.9800
C15—C161.406 (4)C36A—H36C0.9800
C16—C171.395 (4)C43A—C44A1.497 (12)
C17—C181.375 (4)C43A—H43A0.9900
C17—H170.9500C43A—H43B0.9900
C18—C191.380 (4)C44A—H44A0.9800
C19—C201.406 (3)C44A—H44B0.9800
C19—C211.525 (4)C44A—H44C0.9800
C20—H200.9500C49A—C50A1.464 (9)
C21—C221.510 (4)C49A—H49A0.9900
C21—C481.527 (4)C49A—H49B0.9900
C21—H211.0000C50A—C51A1.564 (12)
C22—C271.400 (4)C50A—H50A0.9900
C22—C231.404 (4)C50A—H50B0.9900
C23—C241.387 (4)C51A—C52A1.576 (12)
C24—C251.383 (4)C51A—H51A0.9900
C24—H240.9500C51A—H51B0.9900
C25—C261.385 (4)C52A—H52A0.9800
C26—C271.404 (4)C52A—H52B0.9800
C26—C281.519 (4)C52A—H52C0.9800
C27—H270.9500Cl1B—C31B1.727 (10)
C28—C561.544 (4)C31B—H31C0.9900
C28—H281.0000C31B—H31D0.9900
C29—H29A0.9800C35B—C36B1.456 (14)
C29—H29B0.9800C35B—H35C0.9900
C29—H29C0.9800C35B—H35D0.9900
C30—C31B1.473 (11)C36B—H36D0.9800
C30—C31A1.594 (10)C36B—H36E0.9800
C32—C331.525 (4)C36B—H36F0.9800
C32—H32A0.9900C44B—H44D0.9800
C32—H32B0.9900C44B—H44E0.9800
C33—C34A1.536 (4)C44B—H44F0.9800
C33—H33A0.9900C50B—C51B1.565 (10)
C33—H33B0.9900C50B—H50C0.9900
C37—H37A0.9800C50B—H50D0.9900
C37—H37B0.9800C51B—C52B1.509 (11)
C37—H37C0.9800C51B—H51C0.9900
C38—C391.512 (4)C51B—H51D0.9900
C39—H39A0.9900C52B—H52D0.9800
C39—H39B0.9900C52B—H52E0.9800
C40—C411.517 (4)C52B—H52F0.9800
C2—O1—C29118.3 (2)O7—C45—H45A109.5
C30—O2—C4119.1 (2)O7—C45—H45B109.5
C9—O4—C37117.6 (2)H45A—C45—H45B109.5
C38—O5—C11117.9 (2)O7—C45—H45C109.5
C16—O7—C45117.3 (2)H45A—C45—H45C109.5
C46—O8—C18119.3 (2)H45B—C45—H45C109.5
C23—O10—C53117.4 (3)O9—C46—O8125.9 (3)
C54—O11—C25116.7 (2)O9—C46—C47121.7 (3)
C6—C1—C2118.0 (2)O8—C46—C47112.4 (3)
C6—C1—C28120.6 (2)C46—C47—Cl3115.5 (2)
C2—C1—C28121.2 (2)C46—C47—H47A108.4
O1—C2—C3123.0 (2)Cl3—C47—H47A108.4
O1—C2—C1116.6 (2)C46—C47—H47B108.4
C3—C2—C1120.3 (2)Cl3—C47—H47B108.4
C4—C3—C2119.0 (2)H47A—C47—H47B107.5
C4—C3—H3120.5C21—C48—C49A112.2 (3)
C2—C3—H3120.5C21—C48—H48A109.2
C3—C4—C5123.6 (2)C49A—C48—H48A109.2
C3—C4—O2118.0 (2)C21—C48—H48B109.2
C5—C4—O2118.1 (2)C49A—C48—H48B109.2
C4—C5—C6115.2 (2)H48A—C48—H48B107.9
C4—C5—C7123.4 (2)O10—C53—H53A109.5
C6—C5—C7121.2 (2)O10—C53—H53B109.5
C1—C6—C5123.8 (2)H53A—C53—H53B109.5
C1—C6—H6118.1O10—C53—H53C109.5
C5—C6—H6118.1H53A—C53—H53C109.5
C5—C7—C8111.7 (2)H53B—C53—H53C109.5
C5—C7—C32110.8 (2)O12—C54—O11124.1 (3)
C8—C7—C32113.3 (2)O12—C54—C55127.4 (3)
C5—C7—H7106.9O11—C54—C55108.4 (2)
C8—C7—H7106.9C54—C55—Cl4111.9 (2)
C32—C7—H7106.9C54—C55—H55A109.2
C13—C8—C9117.9 (2)Cl4—C55—H55A109.2
C13—C8—C7123.5 (2)C54—C55—H55B109.2
C9—C8—C7118.6 (2)Cl4—C55—H55B109.2
O4—C9—C10123.7 (2)H55A—C55—H55B107.9
O4—C9—C8115.7 (2)C57—C56—C28111.5 (2)
C10—C9—C8120.6 (2)C57—C56—H56A109.3
C11—C10—C9118.7 (2)C28—C56—H56A109.3
C11—C10—H10120.6C57—C56—H56B109.3
C9—C10—H10120.6C28—C56—H56B109.3
C10—C11—C12123.8 (2)H56A—C56—H56B108.0
C10—C11—O5117.0 (2)C58—C57—C56114.9 (3)
C12—C11—O5119.1 (2)C58—C57—H57A108.5
C11—C12—C13115.3 (2)C56—C57—H57A108.5
C11—C12—C14120.5 (2)C58—C57—H57B108.5
C13—C12—C14124.2 (2)C56—C57—H57B108.5
C8—C13—C12123.6 (2)H57A—C57—H57B107.5
C8—C13—H13118.2C57—C58—C59113.0 (3)
C12—C13—H13118.2C57—C58—H58A109.0
C12—C14—C15112.3 (2)C59—C58—H58A109.0
C12—C14—C40113.7 (2)C57—C58—H58B109.0
C15—C14—C40108.9 (2)C59—C58—H58B109.0
C12—C14—H14107.2H58A—C58—H58B107.8
C15—C14—H14107.2C60—C59—C58114.8 (4)
C40—C14—H14107.2C60—C59—H59A108.6
C20—C15—C16118.3 (2)C58—C59—H59A108.6
C20—C15—C14120.4 (2)C60—C59—H59B108.6
C16—C15—C14121.0 (2)C58—C59—H59B108.6
O7—C16—C17123.6 (2)H59A—C59—H59B107.6
O7—C16—C15116.3 (2)C59—C60—H60A109.5
C17—C16—C15120.0 (2)C59—C60—H60B109.5
C18—C17—C16119.0 (2)H60A—C60—H60B109.5
C18—C17—H17120.5C59—C60—H60C109.5
C16—C17—H17120.5H60A—C60—H60C109.5
C17—C18—C19123.6 (2)H60B—C60—H60C109.5
C17—C18—O8118.6 (2)C30—C31A—Cl1A107.5 (5)
C19—C18—O8117.4 (2)C30—C31A—H31A110.2
C18—C19—C20115.9 (2)Cl1A—C31A—H31A110.2
C18—C19—C21123.6 (2)C30—C31A—H31B110.2
C20—C19—C21120.0 (2)Cl1A—C31A—H31B110.2
C15—C20—C19123.1 (2)H31A—C31A—H31B108.5
C15—C20—H20118.4C33—C34A—C35A115.9 (3)
C19—C20—H20118.4C33—C34A—H34A108.3
C22—C21—C19110.7 (2)C35A—C34A—H34A108.3
C22—C21—C48115.4 (2)C33—C34A—H34B108.3
C19—C21—C48110.0 (2)C35A—C34A—H34B108.3
C22—C21—H21106.8H34A—C34A—H34B107.4
C19—C21—H21106.8C34A—C35A—C36A105.3 (5)
C48—C21—H21106.8C34A—C35A—H35A110.7
C27—C22—C23117.7 (3)C36A—C35A—H35A110.7
C27—C22—C21123.8 (3)C34A—C35A—H35B110.7
C23—C22—C21118.5 (2)C36A—C35A—H35B110.7
O10—C23—C24123.2 (3)H35A—C35A—H35B108.8
O10—C23—C22115.6 (2)C35A—C36A—H36A109.5
C24—C23—C22121.1 (3)C35A—C36A—H36B109.5
C25—C24—C23118.3 (3)H36A—C36A—H36B109.5
C25—C24—H24120.9C35A—C36A—H36C109.5
C23—C24—H24120.9H36A—C36A—H36C109.5
C24—C25—C26124.2 (3)H36B—C36A—H36C109.5
C24—C25—O11116.7 (3)C42—C43A—C44A112.2 (8)
C26—C25—O11119.1 (2)C42—C43A—H43A109.2
C25—C26—C27115.7 (2)C44A—C43A—H43A109.2
C25—C26—C28119.9 (2)C42—C43A—H43B109.2
C27—C26—C28124.4 (3)C44A—C43A—H43B109.2
C22—C27—C26123.0 (3)H43A—C43A—H43B107.9
C22—C27—H27118.5C43A—C44A—H44A109.5
C26—C27—H27118.5C43A—C44A—H44B109.5
C26—C28—C1111.2 (2)H44A—C44A—H44B109.5
C26—C28—C56115.3 (2)C43A—C44A—H44C109.5
C1—C28—C56110.2 (2)H44A—C44A—H44C109.5
C26—C28—H28106.5H44B—C44A—H44C109.5
C1—C28—H28106.5C50A—C49A—C48111.8 (5)
C56—C28—H28106.5C50A—C49A—H49A109.3
O1—C29—H29A109.5C48—C49A—H49A109.3
O1—C29—H29B109.5C50A—C49A—H49B109.3
H29A—C29—H29B109.5C48—C49A—H49B109.3
O1—C29—H29C109.5H49A—C49A—H49B107.9
H29A—C29—H29C109.5C49A—C50A—C51A111.8 (7)
H29B—C29—H29C109.5C49A—C50A—H50A109.3
O3—C30—O2125.7 (3)C51A—C50A—H50A109.3
O3—C30—C31B116.3 (5)C49A—C50A—H50B109.3
O2—C30—C31B116.9 (5)C51A—C50A—H50B109.3
O3—C30—C31A133.8 (4)H50A—C50A—H50B107.9
O2—C30—C31A99.7 (4)C50A—C51A—C52A117.7 (9)
C33—C32—C7113.1 (2)C50A—C51A—H51A107.9
C33—C32—H32A109.0C52A—C51A—H51A107.9
C7—C32—H32A109.0C50A—C51A—H51B107.9
C33—C32—H32B109.0C52A—C51A—H51B107.9
C7—C32—H32B109.0H51A—C51A—H51B107.2
H32A—C32—H32B107.8C51A—C52A—H52A109.5
C32—C33—C34A113.7 (2)C51A—C52A—H52B109.5
C32—C33—H33A108.8H52A—C52A—H52B109.5
C34A—C33—H33A108.8C51A—C52A—H52C109.5
C32—C33—H33B108.8H52A—C52A—H52C109.5
C34A—C33—H33B108.8H52B—C52A—H52C109.5
H33A—C33—H33B107.7C30—C31B—Cl1B116.4 (7)
O4—C37—H37A109.5C30—C31B—H31C108.2
O4—C37—H37B109.5Cl1B—C31B—H31C108.2
H37A—C37—H37B109.5C30—C31B—H31D108.2
O4—C37—H37C109.5Cl1B—C31B—H31D108.2
H37A—C37—H37C109.5H31C—C31B—H31D107.3
H37B—C37—H37C109.5C36B—C35B—H35C109.7
O6—C38—O5124.8 (3)C36B—C35B—H35D109.7
O6—C38—C39127.1 (3)H35C—C35B—H35D108.2
O5—C38—C39108.1 (2)C35B—C36B—H36D109.5
C38—C39—Cl2111.0 (2)C35B—C36B—H36E109.5
C38—C39—H39A109.4H36D—C36B—H36E109.5
Cl2—C39—H39A109.4C35B—C36B—H36F109.5
C38—C39—H39B109.4H36D—C36B—H36F109.5
Cl2—C39—H39B109.4H36E—C36B—H36F109.5
H39A—C39—H39B108.0H44D—C44B—H44E109.5
C41—C40—C14113.9 (2)H44D—C44B—H44F109.5
C41—C40—H40A108.8H44E—C44B—H44F109.5
C14—C40—H40A108.8C51B—C50B—H50C108.0
C41—C40—H40B108.8C51B—C50B—H50D108.0
C14—C40—H40B108.8H50C—C50B—H50D107.2
H40A—C40—H40B107.7C52B—C51B—C50B109.2 (8)
C42—C41—C40113.5 (3)C52B—C51B—H51C109.8
C42—C41—H41A108.9C50B—C51B—H51C109.8
C40—C41—H41A108.9C52B—C51B—H51D109.8
C42—C41—H41B108.9C50B—C51B—H51D109.8
C40—C41—H41B108.9H51C—C51B—H51D108.3
H41A—C41—H41B107.7C51B—C52B—H52D109.5
C43A—C42—C41118.0 (4)C51B—C52B—H52E109.5
C43A—C42—H42A107.8H52D—C52B—H52E109.5
C41—C42—H42A107.8C51B—C52B—H52F109.5
C43A—C42—H42B107.8H52D—C52B—H52F109.5
C41—C42—H42B107.8H52E—C52B—H52F109.5
H42A—C42—H42B107.1
C29—O1—C2—C310.5 (4)C20—C19—C21—C2257.8 (3)
C29—O1—C2—C1168.7 (3)C18—C19—C21—C48101.6 (3)
C6—C1—C2—O1179.9 (2)C20—C19—C21—C4870.9 (3)
C28—C1—C2—O14.9 (4)C19—C21—C22—C27105.4 (3)
C6—C1—C2—C30.7 (4)C48—C21—C22—C2720.3 (4)
C28—C1—C2—C3174.3 (3)C19—C21—C22—C2375.4 (3)
O1—C2—C3—C4178.4 (3)C48—C21—C22—C23158.9 (2)
C1—C2—C3—C40.7 (4)C53—O10—C23—C2414.6 (4)
C2—C3—C4—C50.8 (4)C53—O10—C23—C22166.4 (3)
C2—C3—C4—O2172.6 (3)C27—C22—C23—O10178.7 (2)
C30—O2—C4—C363.4 (4)C21—C22—C23—O100.5 (4)
C30—O2—C4—C5122.8 (3)C27—C22—C23—C242.3 (4)
C3—C4—C5—C60.7 (4)C21—C22—C23—C24178.5 (2)
O2—C4—C5—C6174.1 (2)O10—C23—C24—C25178.6 (2)
C3—C4—C5—C7175.0 (2)C22—C23—C24—C252.5 (4)
O2—C4—C5—C71.6 (4)C23—C24—C25—C260.9 (4)
C2—C1—C6—C52.3 (4)C23—C24—C25—O11178.8 (2)
C28—C1—C6—C5172.8 (2)C54—O11—C25—C2491.2 (3)
C4—C5—C6—C12.3 (4)C54—O11—C25—C2690.8 (3)
C7—C5—C6—C1173.5 (2)C24—C25—C26—C270.9 (4)
C4—C5—C7—C8125.9 (3)O11—C25—C26—C27177.0 (2)
C6—C5—C7—C858.6 (3)C24—C25—C26—C28178.0 (2)
C4—C5—C7—C32106.7 (3)O11—C25—C26—C284.1 (4)
C6—C5—C7—C3268.7 (3)C23—C22—C27—C260.4 (4)
C5—C7—C8—C13102.2 (3)C21—C22—C27—C26179.7 (2)
C32—C7—C8—C1323.8 (3)C25—C26—C27—C221.1 (4)
C5—C7—C8—C979.0 (3)C28—C26—C27—C22177.7 (2)
C32—C7—C8—C9155.0 (2)C25—C26—C28—C174.2 (3)
C37—O4—C9—C108.6 (4)C27—C26—C28—C1107.0 (3)
C37—O4—C9—C8171.2 (2)C25—C26—C28—C56159.5 (2)
C13—C8—C9—O4178.7 (2)C27—C26—C28—C5619.3 (4)
C7—C8—C9—O40.2 (3)C6—C1—C28—C2659.0 (3)
C13—C8—C9—C101.0 (4)C2—C1—C28—C26126.1 (3)
C7—C8—C9—C10179.9 (2)C6—C1—C28—C5670.1 (3)
O4—C9—C10—C11179.4 (2)C2—C1—C28—C56104.8 (3)
C8—C9—C10—C110.3 (4)C4—O2—C30—O36.3 (5)
C9—C10—C11—C121.3 (4)C4—O2—C30—C31B173.9 (6)
C9—C10—C11—O5175.4 (2)C4—O2—C30—C31A164.8 (4)
C38—O5—C11—C1092.6 (3)C5—C7—C32—C3367.3 (3)
C38—O5—C11—C1290.5 (3)C8—C7—C32—C33166.2 (2)
C10—C11—C12—C132.0 (4)C7—C32—C33—C34A69.2 (3)
O5—C11—C12—C13174.6 (2)C11—O5—C38—O62.1 (4)
C10—C11—C12—C14177.0 (2)C11—O5—C38—C39176.1 (2)
O5—C11—C12—C146.4 (3)O6—C38—C39—Cl235.2 (4)
C9—C8—C13—C120.3 (4)O5—C38—C39—Cl2146.7 (2)
C7—C8—C13—C12179.1 (2)C12—C14—C40—C41175.2 (2)
C11—C12—C13—C81.2 (3)C15—C14—C40—C4158.8 (3)
C14—C12—C13—C8177.8 (2)C14—C40—C41—C42177.8 (3)
C11—C12—C14—C1575.8 (3)C40—C41—C42—C43A170.1 (4)
C13—C12—C14—C15105.3 (3)C18—O8—C46—O93.6 (5)
C11—C12—C14—C40160.0 (2)C18—O8—C46—C47175.7 (3)
C13—C12—C14—C4018.9 (3)O9—C46—C47—Cl3174.7 (3)
C12—C14—C15—C2058.4 (3)O8—C46—C47—Cl35.9 (4)
C40—C14—C15—C2068.4 (3)C22—C21—C48—C49A172.4 (3)
C12—C14—C15—C16128.4 (2)C19—C21—C48—C49A61.5 (3)
C40—C14—C15—C16104.8 (3)C25—O11—C54—O123.1 (4)
C45—O7—C16—C1712.5 (4)C25—O11—C54—C55175.5 (2)
C45—O7—C16—C15166.6 (3)O12—C54—C55—Cl416.3 (4)
C20—C15—C16—O7179.1 (2)O11—C54—C55—Cl4165.2 (2)
C14—C15—C16—O75.8 (4)C26—C28—C56—C57175.6 (3)
C20—C15—C16—C170.1 (4)C1—C28—C56—C5757.5 (3)
C14—C15—C16—C17173.4 (2)C28—C56—C57—C58174.5 (3)
O7—C16—C17—C18177.7 (2)C56—C57—C58—C59173.0 (4)
C15—C16—C17—C181.4 (4)C57—C58—C59—C6062.1 (6)
C16—C17—C18—C190.7 (4)O3—C30—C31A—Cl1A25.1 (9)
C16—C17—C18—O8172.3 (2)O2—C30—C31A—Cl1A164.9 (5)
C46—O8—C18—C1773.0 (3)C31B—C30—C31A—Cl1A31.5 (12)
C46—O8—C18—C19113.6 (3)C32—C33—C34A—C35A174.4 (4)
C17—C18—C19—C201.3 (4)C33—C34A—C35A—C36A76.9 (5)
O8—C18—C19—C20174.3 (2)C41—C42—C43A—C44A160.2 (7)
C17—C18—C19—C21171.5 (3)C21—C48—C49A—C50A169.0 (6)
O8—C18—C19—C211.5 (4)C48—C49A—C50A—C51A176.2 (7)
C16—C15—C20—C192.0 (4)C49A—C50A—C51A—C52A42.7 (13)
C14—C15—C20—C19171.3 (2)O3—C30—C31B—Cl1B39.3 (10)
C18—C19—C20—C152.7 (4)O2—C30—C31B—Cl1B151.9 (6)
C21—C19—C20—C15170.4 (2)C31A—C30—C31B—Cl1B98.5 (19)
C18—C19—C21—C22129.7 (3)

Experimental details

Crystal data
Chemical formulaC60H76Cl4O12
Mr1131.01
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)12.4190 (5), 26.1925 (11), 19.1638 (8)
β (°) 107.407 (1)
V3)5948.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.22 × 0.18 × 0.16
Data collection
DiffractometerBruker Kappa DUO APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2006)
Tmin, Tmax0.945, 0.960
No. of measured, independent and
observed [I > 2σ(I)] reflections
37389, 13698, 8473
Rint0.037
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.199, 1.05
No. of reflections13698
No. of parameters694
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.61, 0.60

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

 

Acknowledgements

The authors wish to thank Dr Hong Su from the Chemistry Department of the University of Cape Town for her assistance with the data collection and refinement and the DST – National Research Foundation Centre of Excellence in Catalysis, c*change for financial support.

References

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