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

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ISSN: 2056-9890

4,6,10,12,16,18,22,24-Octa-O-methyl-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 August 2011; accepted 19 August 2011; online 14 September 2011)

The complete molecule of the title compound, C56H80O8, is generated by a crystallographic inversion centre. The dihedral angle between the aromatic ring and the unique half of the molecule is 81.52 (16)°. There are no ππ inter­actions in the crystal structure.

Related literature

For literature related to applications of resorcin[4]arenes, see: Gibson & Rebek (2002[Gibson, C. & Rebek, J. Jr (2002). Org. Lett. 4, 1987-1990.]); Kim et al. (2005[Kim, B., Balasubramanin, R., Pérez-Segarra, W., Wei, A., Decker, B. & Mattay, J. (2005). Supramol. Chem. 17, 173-180.]); Liu et al. (2010[Liu, Y., Liao, P., Cheng, Q. & Hooley, R. J. (2010). J. Am. Chem. Soc. 132, 10383-10390.]); D'Acquarica et al. (2011[D'Acquarica, I., Cerreto, A., Monache, G. D., Subrizi, F., Boffi, A., Tafi, A., Forli, S. & Botta, B. (2011). J. Org. Chem. 76, 4396-4407.]). For related structures, see: Botta et al. (2007[Botta, B., D'Acquarica, I., Monache, G. D., Nevola, L., Tullo, D., Ugozzoli, F. & Pierini, M. (2007). J. Am. Chem. Soc. 129, 11202-11212.]); Iwanek (1998[Iwanek, W. (1998). Tetrahedron, 54, 14089-14094.]); Davis et al. (2001[Davis, C. J., Lewis, P. T., Billodeaux, D. R., Fronczek, F. R., Escobedo, J. O. & Strongin, R. M. (2001). Org. Lett. 3, 2443-2445.]); Gerkensmeier et al. (2001[Gerkensmeier, T., Mattay, J. & Näther, C. (2001). Chem. Eur. J. 7, 465-474.]); Moore & Matthews (2009[Moore, D. & Matthews, S. E. (2009). J. Inclusion Phenom. Macrocycl. Chem. 65, 137-155.]).

[Scheme 1]

Experimental

Crystal data
  • C56H80O8

  • Mr = 881.20

  • Triclinic, [P \overline 1]

  • a = 8.2084 (2) Å

  • b = 14.1270 (2) Å

  • c = 23.1489 (4) Å

  • α = 98.929 (1)°

  • β = 97.914 (1)°

  • γ = 103.581 (1)°

  • V = 2534.93 (8) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 K

  • 0.44 × 0.39 × 0.13 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 42741 measured reflections

  • 12226 independent reflections

  • 7816 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.148

  • S = 0.99

  • 12226 reflections

  • 589 parameters

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 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: 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

Resorcin[4]arenes are easily prepared macromolecules that are used for a range of applications in supramolecular chemistry such as catalysis (Gibson & Rebek, 2002), self-assembled nanoparticles (Kim et al., 2005), molecular recognition (Liu et al., 2010) and noncompetitive inhibitors for R-chymotrypsin (D'Acquarica et al., 2011).

The different conformers of resorcin[4]arenes that can occur in solution have been extensively reported (Moore & Matthews, 2009). Their topology has been classified into four diffrent structures i.e. rccc (cone/crown), rctt (chair), rctc (diamond), rccc (boat). The most commonly reported single-crystal X-ray structures have been the crown and boat isomers (Davis et al., 2001; Gerkensmeier et al., 2001). In the title compound, a pair of aromatic rings are almost coplanar (C8—C9—C11—C12—C13), whereas the others are orthogonal at an angle of 86.91° from the plane facing the side-chains. This creates an rctt conformation (Fig 1). Botta et al. have described the only other rctt octamethoxy-resorcin[4]arene structure thus far (Botta et al., 2007) which had ethyl ester side chains. Iwanek have reported the only rctc octamethoxy resorcinarene (Iwanek, 1998) with isopropyl side chains. There are no ππ interactions in the crystal matrix (Fig. 2).

Related literature top

For literature related to applications of resorcin[4]arenes, see: Gibson & Rebek (2002); Kim et al. (2005); Liu et al. (2010); D'Acquarica et al. (2011). For related structures, see: Botta et al. (2007); Iwanek (1998); Davis et al. (2001); Gerkensmeier et al. (2001); Moore & Matthews (2009).

Experimental top

1,3-Dimethoxybenzene (1.054 g, 7.63 mmol) and hexanal (0.764 g, 7.63 mmol) were added to diethyl ether (20 ml) followed by addition of thionyl chloride (0.907 g, 7.63 mmol). The solution was stirred at room temperature for 24 h. Subsequently, methanol (40 ml) was added, and the mixture was stirred for 1 h. The resulting precipitate was collected by filtration and washed with methanol. The yield was 0.65 g (36%). m.p. = 516–519 K.

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

Refinement top

H atoms were first located in the difference map then positioned geometrically and allowed to ride on their respective parent atoms with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aromatic and C—H = 0.99 Å and Uiso(H) = 1.2Ueq(C) for the aliphatic chain.

Structure description top

Resorcin[4]arenes are easily prepared macromolecules that are used for a range of applications in supramolecular chemistry such as catalysis (Gibson & Rebek, 2002), self-assembled nanoparticles (Kim et al., 2005), molecular recognition (Liu et al., 2010) and noncompetitive inhibitors for R-chymotrypsin (D'Acquarica et al., 2011).

The different conformers of resorcin[4]arenes that can occur in solution have been extensively reported (Moore & Matthews, 2009). Their topology has been classified into four diffrent structures i.e. rccc (cone/crown), rctt (chair), rctc (diamond), rccc (boat). The most commonly reported single-crystal X-ray structures have been the crown and boat isomers (Davis et al., 2001; Gerkensmeier et al., 2001). In the title compound, a pair of aromatic rings are almost coplanar (C8—C9—C11—C12—C13), whereas the others are orthogonal at an angle of 86.91° from the plane facing the side-chains. This creates an rctt conformation (Fig 1). Botta et al. have described the only other rctt octamethoxy-resorcin[4]arene structure thus far (Botta et al., 2007) which had ethyl ester side chains. Iwanek have reported the only rctc octamethoxy resorcinarene (Iwanek, 1998) with isopropyl side chains. There are no ππ interactions in the crystal matrix (Fig. 2).

For literature related to applications of resorcin[4]arenes, see: Gibson & Rebek (2002); Kim et al. (2005); Liu et al. (2010); D'Acquarica et al. (2011). For related structures, see: Botta et al. (2007); Iwanek (1998); Davis et al. (2001); Gerkensmeier et al. (2001); Moore & Matthews (2009).

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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atomic numbering scheme. The H atoms have been omitted clarity. Displacement ellipsoids are drawn at 40% probability, symmetry code (i): 1 - x, -y, -z.
[Figure 2] Fig. 2. The packing of the title compound along the [110] axis. All H atoms have been omitted for clarity.
4,6,10,12,16,18,22,24-Octa-O-methyl-2,8,14,20- tetrapentylresorcin[4]arene top
Crystal data top
C56H80O8Z = 2
Mr = 881.20F(000) = 960
Triclinic, P1Dx = 1.154 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2084 (2) ÅCell parameters from 9018 reflections
b = 14.1270 (2) Åθ = 2.6–28.0°
c = 23.1489 (4) ŵ = 0.08 mm1
α = 98.929 (1)°T = 173 K
β = 97.914 (1)°Plate, colourless
γ = 103.581 (1)°0.44 × 0.39 × 0.13 mm
V = 2534.93 (8) Å3
Data collection top
Bruker APEXII CCD
diffractometer
7816 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.046
Graphite monochromatorθmax = 28.0°, θmin = 0.9°
φ and ω scansh = 1010
42741 measured reflectionsk = 1818
12226 independent reflectionsl = 3030
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0817P)2]
where P = (Fo2 + 2Fc2)/3
12226 reflections(Δ/σ)max = 0.001
589 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C56H80O8γ = 103.581 (1)°
Mr = 881.20V = 2534.93 (8) Å3
Triclinic, P1Z = 2
a = 8.2084 (2) ÅMo Kα radiation
b = 14.1270 (2) ŵ = 0.08 mm1
c = 23.1489 (4) ÅT = 173 K
α = 98.929 (1)°0.44 × 0.39 × 0.13 mm
β = 97.914 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
7816 reflections with I > 2σ(I)
42741 measured reflectionsRint = 0.046
12226 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.148H-atom parameters constrained
S = 0.99Δρmax = 0.39 e Å3
12226 reflectionsΔρmin = 0.26 e Å3
589 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*/Ueq
C10.57192 (19)0.04899 (10)0.06674 (6)0.0238 (3)
H10.45250.02460.06920.029*
C20.65461 (18)0.00564 (10)0.10787 (6)0.0207 (3)
C30.82972 (18)0.04165 (10)0.10628 (6)0.0195 (3)
C40.91774 (18)0.11977 (10)0.05978 (6)0.0208 (3)
H41.03730.14380.05710.025*
C50.84136 (19)0.16501 (10)0.01687 (6)0.0219 (3)
C60.66495 (19)0.12805 (10)0.02208 (6)0.0235 (3)
C70.9370 (2)0.25271 (10)0.03240 (6)0.0239 (3)
H70.85540.29410.03910.029*
C81.03311 (19)0.26193 (10)0.19982 (6)0.0246 (3)
H81.03920.30730.23540.029*
C90.99799 (19)0.28811 (10)0.14464 (6)0.0244 (3)
C100.98417 (18)0.22153 (10)0.09158 (6)0.0221 (3)
C111.01599 (18)0.13015 (10)0.09603 (6)0.0209 (3)
H111.01010.08480.06040.025*
C121.05618 (18)0.10183 (10)0.15035 (6)0.0200 (3)
C131.05902 (18)0.16881 (10)0.20215 (6)0.0221 (3)
C141.08814 (17)0.00129 (10)0.15609 (6)0.0189 (3)
H141.17310.01350.19360.023*
C150.3894 (2)0.10994 (12)0.15630 (7)0.0338 (4)
H15A0.36710.12930.11870.051*
H15B0.34440.16770.18880.051*
H15C0.33360.05770.16370.051*
C160.4127 (2)0.16205 (13)0.00749 (8)0.0373 (4)
H16A0.38280.18290.03010.056*
H16B0.37880.20290.03960.056*
H16C0.35310.09210.00430.056*
C171.0271 (3)0.45754 (13)0.18855 (9)0.0643 (7)
H17A0.95040.44630.21720.096*
H17B1.02560.52040.17580.096*
H17C1.14320.46040.20730.096*
C181.0755 (2)0.19585 (11)0.30801 (7)0.0300 (4)
H18A1.15620.26140.31440.045*
H18B1.10030.16360.34150.045*
H18C0.95910.20340.30490.045*
C191.0918 (2)0.32067 (11)0.01602 (7)0.0289 (4)
H19A1.15280.37180.05150.035*
H19B1.17070.28080.00450.035*
C201.0443 (3)0.37200 (13)0.03473 (8)0.0459 (5)
H20A0.99150.32070.07100.055*
H20B0.95760.40690.02450.055*
C211.1938 (3)0.44644 (15)0.04869 (10)0.0658 (7)
H21A1.14930.48200.07830.079*
H21B1.24960.49610.01200.079*
C221.3244 (4)0.40150 (18)0.07211 (12)0.0925 (10)
H22A1.26640.34240.10350.111*
H22B1.38760.37910.03960.111*
C231.4507 (4)0.4738 (2)0.09782 (13)0.1321 (16)
H23A1.39200.48740.13420.198*
H23B1.54320.44440.10710.198*
H23C1.49790.53590.06870.198*
C240.92534 (19)0.07005 (10)0.16585 (7)0.0255 (3)
H24A0.87100.03250.19370.031*
H24B0.84490.09330.12740.031*
C250.9520 (2)0.16053 (11)0.19023 (8)0.0348 (4)
H25A0.84010.20950.18470.042*
H25B1.02420.19160.16660.042*
C261.0343 (3)0.13830 (14)0.25552 (9)0.0462 (5)
H26A0.96870.10100.27870.055*
H26B1.15100.09480.26030.055*
C271.0449 (3)0.22990 (16)0.28167 (10)0.0611 (6)
H27A0.92870.27440.27600.073*
H27B1.11360.26620.25950.073*
C281.1227 (4)0.2061 (2)0.34712 (12)0.0945 (10)
H28A1.23520.15910.35350.142*
H28B1.13440.26720.36030.142*
H28C1.04880.17660.37000.142*
C290.92260 (19)0.44372 (10)0.56863 (6)0.0225 (3)
H291.04290.46740.57340.027*
C300.83704 (18)0.47882 (9)0.61160 (6)0.0196 (3)
C310.66025 (17)0.44376 (9)0.60632 (6)0.0172 (3)
C320.57479 (18)0.37462 (9)0.55514 (6)0.0172 (3)
H320.45440.35150.55010.021*
C330.65478 (18)0.33708 (9)0.51066 (6)0.0178 (3)
C340.83149 (18)0.37388 (10)0.51865 (6)0.0203 (3)
C350.56261 (18)0.25566 (9)0.45731 (6)0.0187 (3)
H350.64220.21310.45020.022*
C360.49061 (18)0.26418 (10)0.29213 (6)0.0210 (3)
H360.48910.22210.25570.025*
C370.52010 (18)0.23300 (10)0.34572 (6)0.0200 (3)
C380.52755 (18)0.29423 (10)0.40005 (6)0.0184 (3)
C390.49580 (17)0.38639 (9)0.39833 (6)0.0184 (3)
H390.49800.42850.43480.022*
C400.46084 (17)0.41983 (9)0.34553 (6)0.0173 (3)
C410.46333 (18)0.35759 (10)0.29239 (6)0.0191 (3)
C420.42842 (17)0.52173 (9)0.34370 (6)0.0175 (3)
H420.34810.51410.30560.021*
C431.0998 (2)0.58625 (13)0.66741 (8)0.0365 (4)
H43A1.15320.53120.66830.055*
H43B1.14400.63540.70440.055*
H43C1.12600.61740.63360.055*
C441.0860 (2)0.34697 (12)0.48723 (7)0.0324 (4)
H44A1.14740.41750.49680.049*
H44B1.12230.31400.45270.049*
H44C1.11120.31610.52130.049*
C450.5143 (3)0.07023 (12)0.29651 (8)0.0532 (6)
H45A0.40270.06560.27310.080*
H45B0.51650.00540.30620.080*
H45C0.60340.09050.27340.080*
C460.4490 (2)0.33674 (11)0.18674 (6)0.0304 (4)
H46A0.56650.33140.18850.046*
H46B0.41890.36900.15370.046*
H46C0.37150.27020.18050.046*
C470.39980 (19)0.18682 (10)0.46791 (6)0.0225 (3)
H47A0.31900.22680.47710.027*
H47B0.34610.13780.43080.027*
C480.4288 (2)0.13113 (10)0.51825 (7)0.0256 (3)
H48A0.50970.09120.50930.031*
H48B0.48170.17990.55550.031*
C490.2662 (2)0.06318 (13)0.52775 (8)0.0374 (4)
H49A0.18140.10190.53300.045*
H49B0.21890.01060.49180.045*
C500.2925 (2)0.01513 (13)0.58115 (8)0.0406 (4)
H50A0.33480.06770.61740.049*
H50B0.38110.02110.57670.049*
C510.1312 (3)0.0566 (2)0.58920 (13)0.0899 (10)
H51A0.04540.02040.59640.135*
H51B0.15720.08750.62320.135*
H51C0.08710.10810.55320.135*
C520.59415 (19)0.59643 (10)0.33991 (6)0.0221 (3)
H52A0.67190.61130.37880.027*
H52B0.64970.56460.30990.027*
C530.5731 (2)0.69418 (10)0.32391 (7)0.0297 (4)
H53A0.49730.71950.34860.036*
H53B0.68570.74340.33400.036*
C540.5003 (3)0.68609 (13)0.25889 (8)0.0410 (4)
H54A0.38380.64120.24970.049*
H54B0.57080.65560.23410.049*
C550.4927 (3)0.78484 (15)0.24201 (10)0.0575 (6)
H55A0.42290.81560.26690.069*
H55B0.60930.82960.25090.069*
C560.4189 (4)0.7761 (2)0.17737 (12)0.0945 (10)
H56A0.49140.74980.15230.142*
H56B0.41350.84180.16980.142*
H56C0.30390.73120.16800.142*
O10.56951 (13)0.07364 (7)0.15298 (4)0.0257 (2)
O20.59201 (14)0.17402 (8)0.02027 (5)0.0325 (3)
O30.97265 (16)0.37925 (8)0.13885 (5)0.0350 (3)
O41.09114 (14)0.13645 (7)0.25449 (4)0.0283 (3)
O50.91909 (13)0.54939 (7)0.66135 (4)0.0261 (2)
O60.90743 (13)0.33729 (8)0.47391 (4)0.0278 (2)
O70.54300 (15)0.14038 (7)0.34895 (4)0.0301 (3)
O80.43475 (14)0.39443 (7)0.24128 (4)0.0263 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0197 (8)0.0303 (8)0.0234 (8)0.0085 (6)0.0057 (6)0.0063 (6)
C20.0215 (8)0.0224 (7)0.0174 (7)0.0059 (6)0.0010 (6)0.0041 (5)
C30.0198 (8)0.0232 (7)0.0171 (7)0.0085 (6)0.0026 (6)0.0052 (5)
C40.0185 (7)0.0250 (7)0.0198 (7)0.0084 (6)0.0018 (6)0.0042 (6)
C50.0245 (8)0.0223 (7)0.0195 (7)0.0098 (6)0.0004 (6)0.0033 (6)
C60.0262 (8)0.0294 (8)0.0187 (7)0.0139 (7)0.0060 (6)0.0043 (6)
C70.0280 (8)0.0252 (7)0.0191 (7)0.0128 (6)0.0003 (6)0.0002 (6)
C80.0259 (8)0.0253 (7)0.0193 (7)0.0056 (6)0.0032 (6)0.0029 (6)
C90.0249 (8)0.0238 (7)0.0234 (8)0.0076 (6)0.0032 (6)0.0007 (6)
C100.0197 (8)0.0258 (7)0.0199 (7)0.0066 (6)0.0024 (6)0.0021 (6)
C110.0183 (7)0.0239 (7)0.0185 (7)0.0052 (6)0.0032 (6)0.0009 (6)
C120.0151 (7)0.0232 (7)0.0203 (7)0.0037 (6)0.0031 (6)0.0019 (6)
C130.0195 (8)0.0266 (7)0.0185 (7)0.0037 (6)0.0030 (6)0.0033 (6)
C140.0171 (7)0.0217 (7)0.0164 (7)0.0050 (6)0.0013 (5)0.0011 (5)
C150.0189 (8)0.0413 (9)0.0336 (9)0.0016 (7)0.0038 (7)0.0052 (7)
C160.0304 (10)0.0522 (10)0.0357 (10)0.0234 (8)0.0100 (8)0.0049 (8)
C170.116 (2)0.0300 (10)0.0376 (11)0.0288 (12)0.0175 (12)0.0077 (8)
C180.0345 (9)0.0345 (8)0.0193 (8)0.0061 (7)0.0075 (7)0.0019 (6)
C190.0347 (9)0.0233 (7)0.0249 (8)0.0056 (7)0.0008 (7)0.0010 (6)
C200.0613 (13)0.0311 (9)0.0397 (11)0.0055 (9)0.0024 (9)0.0103 (8)
C210.0915 (19)0.0416 (11)0.0523 (13)0.0068 (12)0.0001 (13)0.0225 (10)
C220.115 (2)0.0700 (16)0.0653 (17)0.0333 (16)0.0468 (17)0.0061 (13)
C230.139 (3)0.136 (3)0.072 (2)0.070 (2)0.023 (2)0.0325 (19)
C240.0224 (8)0.0280 (8)0.0258 (8)0.0058 (6)0.0074 (6)0.0027 (6)
C250.0353 (10)0.0287 (8)0.0433 (10)0.0063 (7)0.0173 (8)0.0094 (7)
C260.0498 (12)0.0475 (11)0.0482 (12)0.0150 (9)0.0130 (10)0.0223 (9)
C270.0573 (14)0.0705 (14)0.0784 (17)0.0280 (12)0.0308 (13)0.0490 (13)
C280.098 (2)0.136 (3)0.084 (2)0.052 (2)0.0280 (17)0.079 (2)
C290.0169 (7)0.0254 (7)0.0250 (8)0.0057 (6)0.0044 (6)0.0037 (6)
C300.0202 (8)0.0185 (7)0.0190 (7)0.0054 (6)0.0014 (6)0.0019 (5)
C310.0193 (7)0.0173 (6)0.0176 (7)0.0077 (6)0.0039 (5)0.0060 (5)
C320.0155 (7)0.0178 (6)0.0192 (7)0.0054 (5)0.0019 (5)0.0057 (5)
C330.0211 (7)0.0168 (6)0.0174 (7)0.0081 (6)0.0020 (6)0.0049 (5)
C340.0231 (8)0.0219 (7)0.0192 (7)0.0102 (6)0.0070 (6)0.0047 (6)
C350.0237 (8)0.0184 (6)0.0147 (7)0.0090 (6)0.0009 (6)0.0025 (5)
C360.0241 (8)0.0205 (7)0.0172 (7)0.0058 (6)0.0036 (6)0.0007 (5)
C370.0223 (8)0.0174 (6)0.0205 (7)0.0067 (6)0.0030 (6)0.0028 (5)
C380.0176 (7)0.0202 (7)0.0170 (7)0.0051 (6)0.0022 (5)0.0031 (5)
C390.0188 (7)0.0192 (6)0.0162 (7)0.0045 (6)0.0028 (6)0.0022 (5)
C400.0158 (7)0.0168 (6)0.0196 (7)0.0044 (5)0.0040 (5)0.0037 (5)
C410.0207 (7)0.0200 (7)0.0160 (7)0.0038 (6)0.0023 (6)0.0048 (5)
C420.0193 (7)0.0174 (6)0.0157 (7)0.0061 (6)0.0021 (5)0.0021 (5)
C430.0180 (8)0.0458 (10)0.0355 (9)0.0021 (7)0.0019 (7)0.0108 (8)
C440.0256 (9)0.0426 (9)0.0337 (9)0.0185 (7)0.0094 (7)0.0039 (7)
C450.0998 (18)0.0261 (9)0.0289 (10)0.0269 (10)0.0118 (10)0.0045 (7)
C460.0438 (10)0.0317 (8)0.0169 (7)0.0108 (7)0.0074 (7)0.0048 (6)
C470.0263 (8)0.0193 (7)0.0213 (7)0.0061 (6)0.0014 (6)0.0039 (6)
C480.0297 (9)0.0228 (7)0.0249 (8)0.0066 (6)0.0035 (6)0.0079 (6)
C490.0338 (10)0.0387 (9)0.0422 (10)0.0058 (8)0.0060 (8)0.0218 (8)
C500.0422 (11)0.0429 (10)0.0439 (11)0.0115 (8)0.0125 (9)0.0251 (8)
C510.0470 (14)0.123 (2)0.126 (2)0.0163 (14)0.0252 (15)0.104 (2)
C520.0230 (8)0.0219 (7)0.0230 (7)0.0063 (6)0.0076 (6)0.0053 (6)
C530.0356 (10)0.0213 (7)0.0358 (9)0.0069 (7)0.0156 (7)0.0089 (7)
C540.0529 (12)0.0415 (10)0.0394 (10)0.0214 (9)0.0156 (9)0.0200 (8)
C550.0609 (14)0.0596 (12)0.0794 (16)0.0330 (11)0.0356 (12)0.0489 (12)
C560.110 (2)0.136 (2)0.092 (2)0.079 (2)0.0461 (18)0.090 (2)
O10.0166 (5)0.0309 (5)0.0248 (6)0.0030 (4)0.0032 (4)0.0031 (4)
O20.0275 (6)0.0447 (7)0.0265 (6)0.0164 (5)0.0079 (5)0.0032 (5)
O30.0528 (8)0.0250 (5)0.0251 (6)0.0174 (5)0.0037 (5)0.0030 (4)
O40.0382 (7)0.0284 (5)0.0171 (5)0.0084 (5)0.0040 (5)0.0025 (4)
O50.0169 (5)0.0300 (5)0.0247 (6)0.0017 (4)0.0022 (4)0.0063 (4)
O60.0225 (6)0.0368 (6)0.0244 (6)0.0115 (5)0.0074 (4)0.0019 (5)
O70.0506 (8)0.0198 (5)0.0205 (5)0.0172 (5)0.0007 (5)0.0005 (4)
O80.0404 (7)0.0240 (5)0.0161 (5)0.0109 (5)0.0049 (5)0.0052 (4)
Geometric parameters (Å, º) top
C1—C61.387 (2)C29—C301.3896 (19)
C1—C21.3908 (19)C29—C341.3900 (19)
C1—H10.9500C29—H290.9500
C2—O11.3790 (16)C30—O51.3743 (16)
C2—C31.4009 (19)C30—C311.4004 (19)
C3—C41.3933 (19)C31—C321.3928 (18)
C3—C14i1.5299 (18)C31—C42ii1.5263 (17)
C4—C51.3968 (19)C32—C331.3972 (18)
C4—H40.9500C32—H320.9500
C5—C61.400 (2)C33—C341.3967 (19)
C5—C71.5200 (19)C33—C351.5211 (18)
C6—O21.3740 (16)C34—O61.3752 (15)
C7—C101.530 (2)C35—C381.5262 (18)
C7—C191.534 (2)C35—C471.5317 (19)
C7—H71.0000C35—H351.0000
C8—C131.389 (2)C36—C411.3886 (18)
C8—C91.395 (2)C36—C371.3887 (19)
C8—H80.9500C36—H360.9500
C9—O31.3750 (17)C37—O71.3765 (15)
C9—C101.3996 (19)C37—C381.3965 (18)
C10—C111.3919 (19)C38—C391.3919 (18)
C11—C121.3980 (19)C39—C401.3947 (19)
C11—H110.9500C39—H390.9500
C12—C131.4014 (18)C40—C411.4023 (18)
C12—C141.5257 (18)C40—C421.5300 (17)
C13—O41.3736 (17)C41—O81.3777 (16)
C14—C3i1.5299 (18)C42—C31ii1.5263 (17)
C14—C241.5407 (19)C42—C521.5360 (18)
C14—H141.0000C42—H421.0000
C15—O11.4335 (17)C43—O51.4314 (18)
C15—H15A0.9800C43—H43A0.9800
C15—H15B0.9800C43—H43B0.9800
C15—H15C0.9800C43—H43C0.9800
C16—O21.4249 (19)C44—O61.4252 (18)
C16—H16A0.9800C44—H44A0.9800
C16—H16B0.9800C44—H44B0.9800
C16—H16C0.9800C44—H44C0.9800
C17—O31.4064 (19)C45—O71.3961 (18)
C17—H17A0.9800C45—H45A0.9800
C17—H17B0.9800C45—H45B0.9800
C17—H17C0.9800C45—H45C0.9800
C18—O41.4241 (17)C46—O81.4277 (16)
C18—H18A0.9800C46—H46A0.9800
C18—H18B0.9800C46—H46B0.9800
C18—H18C0.9800C46—H46C0.9800
C19—C201.526 (2)C47—C481.5264 (19)
C19—H19A0.9900C47—H47A0.9900
C19—H19B0.9900C47—H47B0.9900
C20—C211.525 (3)C48—C491.516 (2)
C20—H20A0.9900C48—H48A0.9900
C20—H20B0.9900C48—H48B0.9900
C21—C221.489 (4)C49—C501.514 (2)
C21—H21A0.9900C49—H49A0.9900
C21—H21B0.9900C49—H49B0.9900
C22—C231.528 (3)C50—C511.520 (3)
C22—H22A0.9900C50—H50A0.9900
C22—H22B0.9900C50—H50B0.9900
C23—H23A0.9800C51—H51A0.9800
C23—H23B0.9800C51—H51B0.9800
C23—H23C0.9800C51—H51C0.9800
C24—C251.524 (2)C52—C531.5254 (19)
C24—H24A0.9900C52—H52A0.9900
C24—H24B0.9900C52—H52B0.9900
C25—C261.520 (2)C53—C541.517 (2)
C25—H25A0.9900C53—H53A0.9900
C25—H25B0.9900C53—H53B0.9900
C26—C271.526 (2)C54—C551.519 (2)
C26—H26A0.9900C54—H54A0.9900
C26—H26B0.9900C54—H54B0.9900
C27—C281.514 (3)C55—C561.510 (3)
C27—H27A0.9900C55—H55A0.9900
C27—H27B0.9900C55—H55B0.9900
C28—H28A0.9800C56—H56A0.9800
C28—H28B0.9800C56—H56B0.9800
C28—H28C0.9800C56—H56C0.9800
C6—C1—C2119.56 (14)O5—C30—C31116.04 (12)
C6—C1—H1120.2C29—C30—C31121.34 (13)
C2—C1—H1120.2C32—C31—C30116.62 (12)
O1—C2—C1122.32 (13)C32—C31—C42ii123.23 (12)
O1—C2—C3116.16 (12)C30—C31—C42ii120.10 (12)
C1—C2—C3121.51 (13)C31—C32—C33124.22 (13)
C4—C3—C2116.56 (12)C31—C32—H32117.9
C4—C3—C14i123.66 (13)C33—C32—H32117.9
C2—C3—C14i119.69 (12)C34—C33—C32116.61 (12)
C3—C4—C5124.16 (14)C34—C33—C35119.34 (12)
C3—C4—H4117.9C32—C33—C35123.95 (13)
C5—C4—H4117.9O6—C34—C29122.85 (13)
C4—C5—C6116.57 (13)O6—C34—C33115.71 (12)
C4—C5—C7123.90 (13)C29—C34—C33121.44 (12)
C6—C5—C7119.48 (12)C33—C35—C38113.56 (11)
O2—C6—C1122.73 (13)C33—C35—C47114.02 (11)
O2—C6—C5115.69 (13)C38—C35—C47110.54 (12)
C1—C6—C5121.57 (13)C33—C35—H35106.0
C5—C7—C10112.62 (12)C38—C35—H35106.0
C5—C7—C19114.10 (12)C47—C35—H35106.0
C10—C7—C19111.39 (12)C41—C36—C37119.24 (12)
C5—C7—H7106.0C41—C36—H36120.4
C10—C7—H7106.0C37—C36—H36120.4
C19—C7—H7106.0O7—C37—C36122.64 (12)
C13—C8—C9119.31 (13)O7—C37—C38115.69 (12)
C13—C8—H8120.3C36—C37—C38121.67 (12)
C9—C8—H8120.3C39—C38—C37117.28 (12)
O3—C9—C8122.60 (13)C39—C38—C35123.77 (12)
O3—C9—C10116.08 (13)C37—C38—C35118.91 (12)
C8—C9—C10121.32 (13)C38—C39—C40123.09 (12)
C11—C10—C9117.39 (13)C38—C39—H39118.5
C11—C10—C7123.70 (12)C40—C39—H39118.5
C9—C10—C7118.91 (12)C39—C40—C41117.36 (12)
C10—C11—C12123.19 (13)C39—C40—C42123.08 (12)
C10—C11—H11118.4C41—C40—C42119.50 (12)
C12—C11—H11118.4O8—C41—C36122.85 (12)
C11—C12—C13117.26 (13)O8—C41—C40115.90 (11)
C11—C12—C14123.93 (12)C36—C41—C40121.24 (12)
C13—C12—C14118.74 (12)C31ii—C42—C40112.82 (10)
O4—C13—C8123.07 (12)C31ii—C42—C52114.20 (11)
O4—C13—C12115.54 (12)C40—C42—C52109.85 (11)
C8—C13—C12121.38 (13)C31ii—C42—H42106.5
C12—C14—C3i113.62 (11)C40—C42—H42106.5
C12—C14—C24110.26 (11)C52—C42—H42106.5
C3i—C14—C24114.38 (11)O5—C43—H43A109.5
C12—C14—H14105.9O5—C43—H43B109.5
C3i—C14—H14105.9H43A—C43—H43B109.5
C24—C14—H14105.9O5—C43—H43C109.5
O1—C15—H15A109.5H43A—C43—H43C109.5
O1—C15—H15B109.5H43B—C43—H43C109.5
H15A—C15—H15B109.5O6—C44—H44A109.5
O1—C15—H15C109.5O6—C44—H44B109.5
H15A—C15—H15C109.5H44A—C44—H44B109.5
H15B—C15—H15C109.5O6—C44—H44C109.5
O2—C16—H16A109.5H44A—C44—H44C109.5
O2—C16—H16B109.5H44B—C44—H44C109.5
H16A—C16—H16B109.5O7—C45—H45A109.5
O2—C16—H16C109.5O7—C45—H45B109.5
H16A—C16—H16C109.5H45A—C45—H45B109.5
H16B—C16—H16C109.5O7—C45—H45C109.5
O3—C17—H17A109.5H45A—C45—H45C109.5
O3—C17—H17B109.5H45B—C45—H45C109.5
H17A—C17—H17B109.5O8—C46—H46A109.5
O3—C17—H17C109.5O8—C46—H46B109.5
H17A—C17—H17C109.5H46A—C46—H46B109.5
H17B—C17—H17C109.5O8—C46—H46C109.5
O4—C18—H18A109.5H46A—C46—H46C109.5
O4—C18—H18B109.5H46B—C46—H46C109.5
H18A—C18—H18B109.5C48—C47—C35114.04 (12)
O4—C18—H18C109.5C48—C47—H47A108.7
H18A—C18—H18C109.5C35—C47—H47A108.7
H18B—C18—H18C109.5C48—C47—H47B108.7
C20—C19—C7113.16 (14)C35—C47—H47B108.7
C20—C19—H19A108.9H47A—C47—H47B107.6
C7—C19—H19A108.9C49—C48—C47113.11 (13)
C20—C19—H19B108.9C49—C48—H48A109.0
C7—C19—H19B108.9C47—C48—H48A109.0
H19A—C19—H19B107.8C49—C48—H48B109.0
C21—C20—C19114.37 (17)C47—C48—H48B109.0
C21—C20—H20A108.7H48A—C48—H48B107.8
C19—C20—H20A108.7C50—C49—C48113.07 (14)
C21—C20—H20B108.7C50—C49—H49A109.0
C19—C20—H20B108.7C48—C49—H49A109.0
H20A—C20—H20B107.6C50—C49—H49B109.0
C22—C21—C20114.38 (17)C48—C49—H49B109.0
C22—C21—H21A108.7H49A—C49—H49B107.8
C20—C21—H21A108.7C49—C50—C51113.19 (17)
C22—C21—H21B108.7C49—C50—H50A108.9
C20—C21—H21B108.7C51—C50—H50A108.9
H21A—C21—H21B107.6C49—C50—H50B108.9
C21—C22—C23112.6 (3)C51—C50—H50B108.9
C21—C22—H22A109.1H50A—C50—H50B107.8
C23—C22—H22A109.1C50—C51—H51A109.5
C21—C22—H22B109.1C50—C51—H51B109.5
C23—C22—H22B109.1H51A—C51—H51B109.5
H22A—C22—H22B107.8C50—C51—H51C109.5
C22—C23—H23A109.5H51A—C51—H51C109.5
C22—C23—H23B109.5H51B—C51—H51C109.5
H23A—C23—H23B109.5C53—C52—C42115.35 (12)
C22—C23—H23C109.5C53—C52—H52A108.4
H23A—C23—H23C109.5C42—C52—H52A108.4
H23B—C23—H23C109.5C53—C52—H52B108.4
C25—C24—C14115.33 (13)C42—C52—H52B108.4
C25—C24—H24A108.4H52A—C52—H52B107.5
C14—C24—H24A108.4C54—C53—C52114.01 (13)
C25—C24—H24B108.4C54—C53—H53A108.7
C14—C24—H24B108.4C52—C53—H53A108.7
H24A—C24—H24B107.5C54—C53—H53B108.7
C26—C25—C24114.49 (14)C52—C53—H53B108.7
C26—C25—H25A108.6H53A—C53—H53B107.6
C24—C25—H25A108.6C53—C54—C55113.92 (16)
C26—C25—H25B108.6C53—C54—H54A108.8
C24—C25—H25B108.6C55—C54—H54A108.8
H25A—C25—H25B107.6C53—C54—H54B108.8
C25—C26—C27114.59 (17)C55—C54—H54B108.8
C25—C26—H26A108.6H54A—C54—H54B107.7
C27—C26—H26A108.6C56—C55—C54113.6 (2)
C25—C26—H26B108.6C56—C55—H55A108.8
C27—C26—H26B108.6C54—C55—H55A108.8
H26A—C26—H26B107.6C56—C55—H55B108.8
C28—C27—C26113.6 (2)C54—C55—H55B108.8
C28—C27—H27A108.8H55A—C55—H55B107.7
C26—C27—H27A108.8C55—C56—H56A109.5
C28—C27—H27B108.8C55—C56—H56B109.5
C26—C27—H27B108.8H56A—C56—H56B109.5
H27A—C27—H27B107.7C55—C56—H56C109.5
C27—C28—H28A109.5H56A—C56—H56C109.5
C27—C28—H28B109.5H56B—C56—H56C109.5
H28A—C28—H28B109.5C2—O1—C15117.02 (11)
C27—C28—H28C109.5C6—O2—C16117.76 (12)
H28A—C28—H28C109.5C9—O3—C17118.75 (13)
H28B—C28—H28C109.5C13—O4—C18118.20 (11)
C30—C29—C34119.75 (13)C30—O5—C43116.80 (11)
C30—C29—H29120.1C34—O6—C44117.70 (12)
C34—C29—H29120.1C37—O7—C45119.00 (12)
O5—C30—C29122.62 (13)C41—O8—C46117.68 (11)
C6—C1—C2—O1179.45 (13)C31—C32—C33—C341.21 (19)
C6—C1—C2—C31.7 (2)C31—C32—C33—C35174.97 (12)
O1—C2—C3—C4178.09 (12)C30—C29—C34—O6178.80 (12)
C1—C2—C3—C43.0 (2)C30—C29—C34—C330.6 (2)
O1—C2—C3—C14i5.19 (18)C32—C33—C34—O6178.93 (11)
C1—C2—C3—C14i173.70 (13)C35—C33—C34—O64.70 (18)
C2—C3—C4—C52.1 (2)C32—C33—C34—C290.49 (19)
C14i—C3—C4—C5174.45 (13)C35—C33—C34—C29175.88 (12)
C3—C4—C5—C60.1 (2)C34—C33—C35—C3881.52 (16)
C3—C4—C5—C7177.63 (13)C32—C33—C35—C38102.39 (15)
C2—C1—C6—O2179.54 (13)C34—C33—C35—C47150.64 (12)
C2—C1—C6—C50.7 (2)C32—C33—C35—C4725.45 (18)
C4—C5—C6—O2179.51 (12)C41—C36—C37—O7177.96 (13)
C7—C5—C6—O21.86 (19)C41—C36—C37—C381.7 (2)
C4—C5—C6—C11.5 (2)O7—C37—C38—C39176.61 (12)
C7—C5—C6—C1179.19 (13)C36—C37—C38—C393.1 (2)
C4—C5—C7—C1098.86 (16)O7—C37—C38—C351.04 (19)
C6—C5—C7—C1083.67 (16)C36—C37—C38—C35179.26 (13)
C4—C5—C7—C1929.4 (2)C33—C35—C38—C3932.11 (19)
C6—C5—C7—C19148.07 (14)C47—C35—C38—C3997.51 (15)
C13—C8—C9—O3179.32 (13)C33—C35—C38—C37150.41 (13)
C13—C8—C9—C101.6 (2)C47—C35—C38—C3779.97 (16)
O3—C9—C10—C11177.45 (13)C37—C38—C39—C401.3 (2)
C8—C9—C10—C113.4 (2)C35—C38—C39—C40178.77 (13)
O3—C9—C10—C72.0 (2)C38—C39—C40—C411.9 (2)
C8—C9—C10—C7177.10 (14)C38—C39—C40—C42179.11 (12)
C5—C7—C10—C1129.8 (2)C37—C36—C41—O8179.39 (13)
C19—C7—C10—C1199.88 (16)C37—C36—C41—C401.6 (2)
C5—C7—C10—C9150.77 (13)C39—C40—C41—O8177.60 (12)
C19—C7—C10—C979.56 (16)C42—C40—C41—O80.27 (19)
C9—C10—C11—C121.7 (2)C39—C40—C41—C363.3 (2)
C7—C10—C11—C12178.89 (13)C42—C40—C41—C36179.34 (13)
C10—C11—C12—C131.9 (2)C39—C40—C42—C31ii32.87 (18)
C10—C11—C12—C14178.79 (13)C41—C40—C42—C31ii149.96 (13)
C9—C8—C13—O4178.79 (13)C39—C40—C42—C5295.80 (15)
C9—C8—C13—C122.1 (2)C41—C40—C42—C5281.38 (15)
C11—C12—C13—O4177.07 (12)C33—C35—C47—C4860.43 (16)
C14—C12—C13—O40.02 (19)C38—C35—C47—C48170.21 (11)
C11—C12—C13—C83.8 (2)C35—C47—C48—C49179.75 (13)
C14—C12—C13—C8179.12 (13)C47—C48—C49—C50174.79 (14)
C11—C12—C14—C3i32.57 (19)C48—C49—C50—C51177.45 (18)
C13—C12—C14—C3i150.54 (13)C31ii—C42—C52—C5365.20 (16)
C11—C12—C14—C2497.35 (16)C40—C42—C52—C53166.90 (12)
C13—C12—C14—C2479.54 (16)C42—C52—C53—C5474.83 (17)
C5—C7—C19—C2063.96 (17)C52—C53—C54—C55175.36 (14)
C10—C7—C19—C20167.15 (13)C53—C54—C55—C56179.55 (18)
C7—C19—C20—C21175.30 (16)C1—C2—O1—C150.5 (2)
C19—C20—C21—C2265.6 (3)C3—C2—O1—C15178.42 (13)
C20—C21—C22—C23167.7 (2)C1—C6—O2—C1620.1 (2)
C12—C14—C24—C25162.65 (12)C5—C6—O2—C16160.93 (13)
C3i—C14—C24—C2567.83 (17)C8—C9—O3—C1717.2 (2)
C14—C24—C25—C2673.33 (18)C10—C9—O3—C17163.64 (17)
C24—C25—C26—C27174.15 (15)C8—C13—O4—C188.3 (2)
C25—C26—C27—C28178.36 (18)C12—C13—O4—C18172.56 (13)
C34—C29—C30—O5178.55 (13)C29—C30—O5—C430.0 (2)
C34—C29—C30—C311.3 (2)C31—C30—O5—C43179.86 (13)
O5—C30—C31—C32177.96 (11)C29—C34—O6—C4419.75 (19)
C29—C30—C31—C321.94 (19)C33—C34—O6—C44160.84 (13)
O5—C30—C31—C42ii4.43 (18)C36—C37—O7—C458.4 (2)
C29—C30—C31—C42ii175.67 (12)C38—C37—O7—C45171.30 (16)
C30—C31—C32—C331.92 (19)C36—C41—O8—C465.6 (2)
C42ii—C31—C32—C33175.61 (12)C40—C41—O8—C46175.33 (13)
Symmetry codes: (i) x+2, y, z; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC56H80O8
Mr881.20
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)8.2084 (2), 14.1270 (2), 23.1489 (4)
α, β, γ (°)98.929 (1), 97.914 (1), 103.581 (1)
V3)2534.93 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.44 × 0.39 × 0.13
Data collection
DiffractometerBruker APEXII CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
42741, 12226, 7816
Rint0.046
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.148, 0.99
No. of reflections12226
No. of parameters589
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.26

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

 

Acknowledgements

The authors thank Dr Manuel Fernandes from the University of the Witwatersrand for his assistance with the data collection and refinement.

References

First citationBotta, B., D'Acquarica, I., Monache, G. D., Nevola, L., Tullo, D., Ugozzoli, F. & Pierini, M. (2007). J. Am. Chem. Soc. 129, 11202–11212.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationBruker (2006). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationD'Acquarica, I., Cerreto, A., Monache, G. D., Subrizi, F., Boffi, A., Tafi, A., Forli, S. & Botta, B. (2011). J. Org. Chem. 76, 4396–4407.  CAS PubMed Google Scholar
First citationDavis, C. J., Lewis, P. T., Billodeaux, D. R., Fronczek, F. R., Escobedo, J. O. & Strongin, R. M. (2001). Org. Lett. 3, 2443–2445.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationGerkensmeier, T., Mattay, J. & Näther, C. (2001). Chem. Eur. J. 7, 465–474.  Web of Science CrossRef PubMed CAS Google Scholar
First citationGibson, C. & Rebek, J. Jr (2002). Org. Lett. 4, 1987–1990.  Web of Science CrossRef Google Scholar
First citationIwanek, W. (1998). Tetrahedron, 54, 14089–14094.  Web of Science CSD CrossRef CAS Google Scholar
First citationKim, B., Balasubramanin, R., Pérez-Segarra, W., Wei, A., Decker, B. & Mattay, J. (2005). Supramol. Chem. 17, 173–180.  Web of Science CrossRef CAS Google Scholar
First citationLiu, Y., Liao, P., Cheng, Q. & Hooley, R. J. (2010). J. Am. Chem. Soc. 132, 10383–10390.  Web of Science CrossRef CAS PubMed Google Scholar
First citationMoore, D. & Matthews, S. E. (2009). J. Inclusion Phenom. Macrocycl. Chem. 65, 137–155.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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