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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 6| June 2009| Pages o1336-o1337

5,11,17,23-Tetra-tert-butyl-25,27-bis­­[2-(4-nitro­phen­­oxy)eth­­oxy]calix[4]arene-26,28-diol aceto­nitrile tetra­solvate

aDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
*Correspondence e-mail: chdsguo@sdnu.edu.cn

(Received 17 April 2009; accepted 14 May 2009; online 20 May 2009)

In the crystal structure of the title compound, C60H70N2O10·4CH3CN, the calix[4]arene mol­ecule adopts an open-cone conformation with two intra­molecular O—H⋯O hydrogen bonds. The four benzene rings of the calix[4]arene are twisted to the mean plane defined by four methyl­ene C atoms bridging the benzene rings, with dihedral angles ranging from 57.74 (10) to 65.99 (12)°. Two pendant nitro­phenyl rings are nearly perpendicular to each other, the dihedral angle being 70.9 (3)°. The asymmetric unit of the crystal structure contains four acetonitrile solvent mol­ecules, one of which lies in the calix cavity and makes C—H⋯π inter­actions and another links with the calix[4]arene via C—H⋯O hydrogen bonding. One tert-butyl group is disordered over two sets of sites, with a 0.736 (13):0.264 (13) occupancy ratio.

Related literature

For general background to the chemistry of calix[4]arenes, see: Gutsche (1998[Gutsche, C. D. (1998). Calixarenes Revisited. RSC Monographs in Chemistry. Cambridge: Royal Society of Chemistry.]). For related crystal structures, see: Singh et al. (2004[Singh, N., Kumar, M. & Hundal, G. (2004). Tetrahedron 60, 5393-5405.]); Bolte et al. (2003[Bolte, M., Danila, C. & Böhmer, V. (2003). Acta Cryst. E59, o533-o534.]); Zeng et al. (2002[Zeng, X.-S., Weng, L.-H., Chen, L.-X., Xu, F.-B., Li, Q.-S., Leng, X.-B., He, X.-W. & Zhang, Z.-Z. (2002). Tetrahedron, 58, 2647-2658.]); Gale et al. (1998[Gale, P. A., Chen, Z., Drew, M. G. B., Heath, J. A. & Beer, P. D. (1998). Polyhedron, 17, 405-412.]); Drew et al. (1997[Drew, M. G. B., Beer, P. D. & Ogden, M. I. (1997). Acta Cryst. C53, 472-474.]); Böhmer et al. (1993[Böhmer, V., Ferguson, G., Gallagher, J. F., Lough, A. J., McKervey, M. A., Madigan, E., Moran, M. B., Phillips, J. & Williams, J. (1993). J. Chem. Soc. Perkin Trans. 1, pp. 1521-1527.]); Bugge et al. (1992[Bugge, K.-E., Verboom, W., Reinhoudt, D. N. & Harkema, S. (1992). Acta Cryst. C48, 1848-1851.]). For C—H⋯π contacts, see: Tsuzuki et al. (2000[Tsuzuki, S., Honda, K., Uchimaru, T., Mikami, M. & Tanabe, K. (2000). J. Am. Chem. Soc. 122, 3746-3753.]); Umezawa et al. (1998[Umezawa, Y., Tsuboyama, S., Honda, K., Uzawa, J. & Nishio, M. (1998). Bull. Chem. Soc. Jpn, 71, 1207-1213.]). For inclusion complexes, see: McKervey et al. (1986[McKervey, M. A., Seward, E. M., Ferguson, G. & Ruhl, B. L. (1986). J. Org. Chem. 51, 3581-3584.]).

[Scheme 1]

Experimental

Crystal data
  • C60H70N2O10·4C2H3N

  • Mr = 1143.40

  • Triclinic, [P \overline 1]

  • a = 13.195 (3) Å

  • b = 13.388 (3) Å

  • c = 19.692 (5) Å

  • α = 71.978 (3)°

  • β = 84.022 (3)°

  • γ = 82.230 (3)°

  • V = 3270.5 (13) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 K

  • 0.51 × 0.35 × 0.15 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: none

  • 15816 measured reflections

  • 11155 independent reflections

  • 7114 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.114

  • wR(F2) = 0.349

  • S = 1.05

  • 11155 reflections

  • 775 parameters

  • 5 restraints

  • H-atom parameters constrained

  • Δρmax = 0.78 e Å−3

  • Δρmin = −0.64 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O3 0.82 1.99 2.802 (6) 171
O2—H2⋯O4 0.82 1.97 2.781 (4) 176
C50—H50C⋯O7i 0.96 2.59 3.487 (10) 156
C68—H68B⋯O10 0.96 2.39 3.247 (13) 148
C65—H65ACg1 0.96 2.66 3.590 (6) 163
Symmetry code: (i) -x+1, -y+1, -z+1. Cg1 is the centroid of the C42–C47 ring.

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART 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.

Supporting information


Comment top

Calix[4]arenes have been attracting much interest because they possess a versatile three-dimensional cavity and are ideal scaffolds for the construction of supramolecular systems. In particular, the lower or upper rim of a calix[4]arene platform can be modified to achieve more sophisticated receptors with a specific affinity and selectivity for ion recognition (Gutsche, 1998). Several crystal structures of 1,3-substituted cone calix[4]arene derivatives (Singh et al., 2004; Bolte et al., 2003; Zeng et al., 2002; Gale et al., 1998; Drew et al., 1997; Böhmer et al., 1993; Bugge et al., 1992) have been described. We report here the crystal structure of a new 1,3-substituted calix[4]arene, C60H70N2O10.4CH3CN, namely 5,11,17,23-tetra-tert-butyl-25,27-bis[2-(4-nitrophenoxy)ethoxy]-26,28-dihydroxycalix[4]arene acetonitrile tetrasolvate.

In the crystal structure of the title compound, as shown in Fig. 1, the molecule of the calix[4]arene adopts an open-cone conformation, in which either phenol hydroxy group links with one neighboring ethereal O atom via an intramolecular O—H···O hydrogen bond (Table 1) and one t-butyl group shows rotational disorder. The four benzene rings of the calix[4]arene are twisted to the virtual plane defined by four methylene C atoms bridging the phenolic rings with dihedral angles ranging from 57.74 (10) to 65.99 (12)°. Two pendant nitrophenyl rings are nearly perpendicular to each other, the dihedral angle being 70.9 (3)°. This conformation results in a distance of 4.005 (6) Å between diametrically opposed atoms O1 and O2, almost same as 4.289 (6) Å between O3 and O4.

There are four acetonitrile solvate molecules in the asymmetric unit of the crystal structure, one of which lies in the calix cavity with C—H···π contacts (Umezawa et al., 1998; Tsuzuki et al., 2000) and another links with the calix[4]arene via C—H···O hydrogen bonding (Table 1). The apolar end of the acetonitrile is held in the cavity, while the polar one remains outside, similar to the related cone calix[4]arene system (McKervey et al., 1986) where an acetonitrile molecule is included. The intermolecular C—H···O hydrogen bonds (Table 1) and the remaining acetonitrile molecules stabilize the molecular packing.

Related literature top

For general background to the chemistry of calix[4]arenes, see: Gutsche (1998). For related crystal structures, see: Singh et al. (2004); Bolte et al. (2003); Zeng et al. (2002); Gale et al. (1998); Drew et al. (1997); Böhmer et al. (1993); Bugge et al. (1992). For C—H···π contacts, see: Tsuzuki et al. (2000); Umezawa et al. (1998). For inclusions, see: McKervey et al. (1986).

Experimental top

To a refluxing suspension of p-tert-butylcalix[4]arene (1.112 g, 1.50 mmol) and anhydrous potassium carbonate (0.228 g, 1.65 mmol) in dry acetonitrile (15 ml) was added 2-(4-nitrophenoxy)ethyl-4-methylbenzenesulfonate (1.144 g, 3.00 mmol) in dry acetonitrile (15 ml) dropwise. The mixture was stirred and refluxed under a nitrogen atmosphere for 46 h and cooled to room temperature. The solvent was removed under reduced pressure. The residue was neutralized with diluted hydrochloric acid and extracted with dichloromethane. The organic layer was washed with saturated sodium hydrogen carbonate and brine, and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure, the residue was purified by flash column chromatography (silica gel, ethyl acetate/hexane/dichloromethane = 1:12:4, RF = 1/2) to give the title compound in 88% yield as a white solid, m.p. 397–399 K. Single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of a solution in acetonitrile at 298 K.

Refinement top

All H atoms were placed in geometrically idealized positions and refined using a riding model, with C—H distances of 0.93–0.97 Å, and with Uiso(H) values of 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for the other H atoms. In the title compound, one tert-butyl group (C1–C4) is rotational disordered over two sites; the site-occupancies were refined to 0.736 (13):0.264 (13). The C—C bond lengths involving the disordered atoms were restrained to be similar. The C67—C68 and C67—N6 bond lengths were restrained. As the quality of the crystal is poor the accuracy of the determination is low.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. The minor disordered component and H atoms have been omitted for clarity.
5,11,17,23-Tetra-tert-butyl-25,27-bis[2-(4- nitrophenoxy)ethoxy]calix[4]arene-26,28-diol acetonitrile tetrasolvate top
Crystal data top
C60H70N2O10·4C2H3NZ = 2
Mr = 1143.40F(000) = 1224
Triclinic, P1Dx = 1.161 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.195 (3) ÅCell parameters from 4717 reflections
b = 13.388 (3) Åθ = 2.6–27.2°
c = 19.692 (5) ŵ = 0.08 mm1
α = 71.978 (3)°T = 173 K
β = 84.022 (3)°Block, colourless
γ = 82.230 (3)°0.51 × 0.35 × 0.15 mm
V = 3270.5 (13) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
7114 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 25.0°, θmin = 1.6°
ϕ and ω scansh = 1515
15816 measured reflectionsk = 1515
11155 independent reflectionsl = 1323
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)] = 0.114Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.349H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1473P)2 + 8.6696P]
where P = (Fo2 + 2Fc2)/3
11155 reflections(Δ/σ)max = 0.005
775 parametersΔρmax = 0.78 e Å3
5 restraintsΔρmin = 0.64 e Å3
Crystal data top
C60H70N2O10·4C2H3Nγ = 82.230 (3)°
Mr = 1143.40V = 3270.5 (13) Å3
Triclinic, P1Z = 2
a = 13.195 (3) ÅMo Kα radiation
b = 13.388 (3) ŵ = 0.08 mm1
c = 19.692 (5) ÅT = 173 K
α = 71.978 (3)°0.51 × 0.35 × 0.15 mm
β = 84.022 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
7114 reflections with I > 2σ(I)
15816 measured reflectionsRint = 0.049
11155 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.1145 restraints
wR(F2) = 0.349H-atom parameters constrained
S = 1.05Δρmax = 0.78 e Å3
11155 reflectionsΔρmin = 0.64 e Å3
775 parameters
Special details top

Experimental. 1H NMR (300 MHz, CDCl3): δ 8.19 (d, 4H, J = 9.20 Hz), 7.09 (s, 2H), 7.06 (s, 4H), 6.99 (d, 4H, J = 9.20 Hz), 6.82 (s, 4H), 4.35 (s, 8H), 4.33 (d, 4H, J = 13.02 Hz), 3.31 (d, 4H, J = 13.02 Hz), 1.29 (s, 18H), 0.98 (s, 18H).

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)
C10.2547 (7)0.3466 (10)0.8947 (5)0.069 (3)0.739 (13)
H1A0.22560.33670.94280.104*0.739 (13)
H1B0.24530.28720.87950.104*0.739 (13)
H1C0.22130.40990.86350.104*0.739 (13)
C20.3929 (11)0.4421 (10)0.9200 (6)0.072 (4)0.739 (13)
H2A0.46560.44300.92010.107*0.739 (13)
H2B0.36260.43010.96790.107*0.739 (13)
H2C0.36360.50880.89010.107*0.739 (13)
C30.4147 (10)0.2469 (7)0.9405 (5)0.072 (4)0.739 (13)
H3A0.48770.24350.94160.107*0.739 (13)
H3B0.39880.19300.92170.107*0.739 (13)
H3C0.38340.23610.98810.107*0.739 (13)
C40.3731 (5)0.3569 (5)0.8920 (3)0.0485 (15)
C50.4236 (4)0.3688 (4)0.8157 (3)0.0390 (13)
C60.3685 (4)0.3745 (4)0.7580 (3)0.0370 (12)
H60.29780.37400.76490.044*
C70.4149 (4)0.3810 (4)0.6897 (3)0.0306 (11)
C80.5219 (4)0.3828 (4)0.6790 (2)0.0303 (11)
C90.5803 (4)0.3783 (4)0.7355 (3)0.0322 (11)
C100.5309 (4)0.3711 (4)0.8028 (3)0.0363 (12)
H100.56980.36770.84040.044*
C110.6975 (4)0.3713 (4)0.7274 (3)0.0342 (11)
H11A0.71940.40940.67870.041*
H11B0.72180.40400.75940.041*
C120.7438 (3)0.2563 (4)0.7448 (3)0.0293 (11)
C130.7655 (3)0.2053 (4)0.6906 (2)0.0275 (10)
C140.7975 (3)0.0963 (4)0.7087 (3)0.0285 (10)
C150.8073 (3)0.0420 (4)0.7807 (3)0.0315 (11)
H150.82740.03030.79320.038*
C160.7887 (4)0.0896 (4)0.8355 (3)0.0335 (11)
C170.7542 (4)0.1987 (4)0.8148 (3)0.0326 (11)
H170.73810.23240.85000.039*
C180.8001 (4)0.0302 (4)0.9147 (3)0.0416 (13)
C190.6944 (5)0.0345 (6)0.9561 (3)0.0621 (18)
H19A0.66590.10690.94760.093*
H19B0.70220.00241.00640.093*
H19C0.64940.00290.94000.093*
C200.8751 (5)0.0844 (6)0.9452 (3)0.0568 (17)
H20A0.94200.07870.92140.085*
H20B0.87900.05020.99560.085*
H20C0.85020.15770.93710.085*
C210.8431 (6)0.0850 (5)0.9263 (3)0.072 (2)
H21A0.79860.11930.90730.107*
H21B0.84760.12000.97660.107*
H21C0.91010.08830.90240.107*
C220.8396 (4)0.2765 (4)0.5701 (3)0.0354 (12)
H22A0.83450.23540.53800.042*
H22B0.90160.24910.59530.042*
C230.8444 (4)0.3907 (4)0.5278 (3)0.0322 (11)
H23A0.89900.39690.49020.039*
H23B0.78020.42000.50580.039*
C240.8708 (3)0.5528 (4)0.5498 (3)0.0313 (11)
C250.8717 (5)0.6058 (5)0.6011 (3)0.0485 (15)
H250.86770.56780.64940.058*
C260.8784 (5)0.7130 (5)0.5813 (3)0.0556 (16)
H260.87870.74730.61570.067*
C270.8846 (4)0.7684 (4)0.5092 (3)0.0388 (12)
C280.8843 (4)0.7170 (4)0.4582 (3)0.0366 (12)
H280.89000.75500.40990.044*
C290.8755 (4)0.6102 (4)0.4779 (3)0.0334 (11)
H290.87270.57690.44320.040*
C300.8120 (3)0.0326 (4)0.6552 (3)0.0295 (10)
H30A0.87270.01780.66520.035*
H30B0.82210.07990.60710.035*
C310.7182 (3)0.0269 (4)0.6594 (2)0.0280 (10)
C320.6346 (4)0.0221 (4)0.6168 (2)0.0289 (10)
C330.5466 (4)0.0287 (4)0.6241 (2)0.0307 (11)
C340.5401 (4)0.1265 (4)0.6752 (3)0.0368 (12)
H340.48060.15920.68050.044*
C350.6199 (4)0.1770 (4)0.7186 (3)0.0370 (12)
C360.7094 (4)0.1248 (4)0.7083 (3)0.0324 (11)
H360.76440.15810.73580.039*
C370.6147 (5)0.2837 (4)0.7760 (3)0.0445 (14)
C380.6961 (6)0.3656 (5)0.7568 (4)0.0629 (19)
H38A0.68180.37450.71230.094*
H38B0.69470.43190.79380.094*
H38C0.76260.34170.75220.094*
C390.6358 (6)0.2736 (5)0.8489 (3)0.0618 (18)
H39A0.70290.25190.84610.093*
H39B0.63210.34060.88490.093*
H39C0.58550.22190.86110.093*
C400.5086 (5)0.3241 (6)0.7832 (4)0.068 (2)
H40A0.45620.27150.79180.103*
H40B0.50650.38790.82250.103*
H40C0.49710.33820.73990.103*
C410.4530 (4)0.0235 (4)0.5799 (3)0.0356 (12)
H41A0.47640.06570.53270.043*
H41B0.41630.03110.57410.043*
C420.3802 (3)0.0938 (4)0.6162 (3)0.0323 (11)
C430.3087 (4)0.0466 (4)0.6706 (3)0.0380 (12)
H430.30240.02500.68120.046*
C440.2465 (4)0.1071 (4)0.7093 (3)0.0363 (12)
C450.2605 (4)0.2121 (4)0.6934 (3)0.0374 (12)
H450.22080.25160.71980.045*
C460.3309 (3)0.2633 (4)0.6397 (2)0.0333 (11)
C470.3896 (3)0.2003 (4)0.6010 (2)0.0319 (11)
C480.1656 (4)0.0584 (5)0.7686 (3)0.0496 (15)
C490.1701 (7)0.0603 (6)0.7842 (5)0.092 (3)
H49A0.15070.07580.74320.138*
H49B0.12370.08800.82460.138*
H49C0.23850.09220.79460.138*
C500.0580 (5)0.1101 (7)0.7444 (4)0.079 (2)
H50A0.05530.18550.73330.118*
H50B0.00730.08450.78230.118*
H50C0.04460.09250.70280.118*
C510.1810 (5)0.0845 (6)0.8371 (3)0.065 (2)
H51A0.24800.05500.85290.098*
H51B0.13010.05500.87370.098*
H51C0.17440.15970.82770.098*
C520.3504 (4)0.3764 (4)0.6306 (3)0.0348 (12)
H52A0.28540.41960.63210.042*
H52B0.38590.40500.58430.042*
C530.4231 (4)0.2907 (5)0.4771 (3)0.0424 (13)
H53A0.36760.34620.47710.051*
H53B0.39750.23600.46300.051*
C540.5112 (4)0.3343 (4)0.4267 (3)0.0385 (12)
H54A0.48890.36680.37870.046*
H54B0.53840.38710.44200.046*
C550.6794 (4)0.2639 (4)0.3893 (3)0.0308 (11)
C560.6960 (4)0.3571 (4)0.3360 (3)0.0470 (15)
H560.64470.41350.32630.056*
C570.7906 (5)0.3650 (5)0.2974 (4)0.0610 (19)
H570.80270.42670.26110.073*
C580.8660 (4)0.2816 (4)0.3128 (3)0.0456 (14)
C590.8509 (4)0.1895 (4)0.3659 (3)0.0406 (13)
H590.90270.13360.37560.049*
C600.7566 (4)0.1811 (4)0.4049 (3)0.0350 (11)
H600.74560.11960.44170.042*
C611.0401 (8)0.6203 (8)0.1833 (6)0.105 (3)
H61A1.09380.56360.18520.157*
H61B1.06960.68430.17770.157*
H61C0.99980.62950.14350.157*
C620.9756 (6)0.5953 (7)0.2489 (6)0.085 (3)
C630.7033 (10)0.2776 (8)1.0540 (4)0.115 (4)
H63A0.75040.21471.05970.173*
H63B0.63440.25881.06450.173*
H63C0.71790.31411.08620.173*
C640.7141 (6)0.3450 (6)0.9816 (4)0.072 (2)
C650.5154 (4)0.0915 (5)0.7801 (3)0.0500 (15)
H65A0.46390.12540.74690.075*
H65B0.57480.06590.75530.075*
H65C0.53380.14130.80150.075*
C660.4757 (5)0.0040 (5)0.8351 (4)0.0561 (17)
C671.0242 (10)0.3631 (11)0.0428 (9)0.191 (8)
C681.1128 (8)0.3882 (10)0.0768 (6)0.124 (4)
H68A1.17530.34930.06520.186*
H68B1.09950.36860.12780.186*
H68C1.11940.46250.05870.186*
C1'0.443 (2)0.382 (3)0.9414 (12)0.080 (11)0.261 (13)
H1'10.40540.38410.98540.120*0.261 (13)
H1'20.46800.44960.91800.120*0.261 (13)
H1'30.50070.32850.95150.120*0.261 (13)
C2'0.321 (3)0.2532 (16)0.9184 (16)0.098 (14)0.261 (13)
H2'10.27130.25490.88570.147*0.261 (13)
H2'20.28780.24660.96510.147*0.261 (13)
H2'30.37210.19400.92080.147*0.261 (13)
C3'0.2903 (18)0.4530 (16)0.8839 (13)0.067 (9)0.261 (13)
H3'10.32290.51700.86910.101*0.261 (13)
H3'20.25220.44720.92890.101*0.261 (13)
H3'30.24480.45450.84860.101*0.261 (13)
N10.9639 (4)0.2891 (4)0.2696 (3)0.0644 (16)
N20.8937 (4)0.8818 (4)0.4872 (3)0.0566 (14)
N30.9248 (6)0.5756 (7)0.3004 (5)0.114 (3)
N40.4436 (6)0.0641 (6)0.8780 (5)0.111 (3)
N50.7228 (7)0.3959 (6)0.9247 (4)0.100 (2)
N60.9436 (18)0.342 (2)0.031 (2)0.45 (3)
O10.6488 (2)0.1190 (3)0.56909 (18)0.0364 (8)
H10.59300.15360.56020.055*
O20.5649 (3)0.3939 (3)0.61067 (17)0.0381 (9)
H20.62110.35890.61250.057*
O30.4624 (2)0.2478 (3)0.54692 (16)0.0337 (8)
O40.7515 (2)0.2675 (2)0.62072 (16)0.0291 (7)
O50.8632 (3)0.4473 (3)0.57552 (17)0.0365 (8)
O60.5876 (2)0.2470 (3)0.42839 (18)0.0350 (8)
O70.9145 (6)0.9262 (4)0.4246 (3)0.0969 (15)
O80.8850 (6)0.9283 (4)0.5324 (3)0.0969 (15)
O91.0274 (4)0.2139 (5)0.2778 (4)0.1034 (16)
O100.9803 (4)0.3736 (5)0.2274 (4)0.1034 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.061 (6)0.108 (9)0.046 (5)0.026 (6)0.023 (4)0.034 (5)
C20.102 (10)0.069 (7)0.051 (6)0.028 (7)0.031 (6)0.031 (6)
C30.110 (10)0.053 (6)0.042 (5)0.007 (5)0.022 (5)0.008 (4)
C40.054 (4)0.062 (4)0.031 (3)0.003 (3)0.009 (2)0.022 (3)
C50.044 (3)0.034 (3)0.034 (3)0.004 (2)0.006 (2)0.010 (2)
C60.031 (3)0.037 (3)0.036 (3)0.006 (2)0.003 (2)0.007 (2)
C70.026 (2)0.025 (2)0.037 (3)0.0058 (19)0.002 (2)0.008 (2)
C80.034 (3)0.025 (2)0.027 (2)0.007 (2)0.000 (2)0.0053 (19)
C90.038 (3)0.022 (2)0.034 (3)0.000 (2)0.001 (2)0.006 (2)
C100.045 (3)0.031 (3)0.033 (3)0.003 (2)0.003 (2)0.012 (2)
C110.031 (3)0.033 (3)0.039 (3)0.002 (2)0.003 (2)0.012 (2)
C120.017 (2)0.031 (2)0.039 (3)0.0042 (19)0.0008 (19)0.010 (2)
C130.018 (2)0.033 (3)0.031 (2)0.0054 (19)0.0015 (18)0.008 (2)
C140.019 (2)0.027 (2)0.038 (3)0.0016 (18)0.0002 (18)0.009 (2)
C150.022 (2)0.028 (2)0.041 (3)0.0006 (19)0.003 (2)0.007 (2)
C160.025 (2)0.037 (3)0.038 (3)0.002 (2)0.003 (2)0.010 (2)
C170.024 (2)0.041 (3)0.034 (3)0.003 (2)0.0000 (19)0.014 (2)
C180.036 (3)0.049 (3)0.036 (3)0.004 (2)0.005 (2)0.008 (2)
C190.050 (4)0.084 (5)0.038 (3)0.007 (3)0.002 (3)0.001 (3)
C200.047 (4)0.079 (5)0.038 (3)0.000 (3)0.013 (3)0.008 (3)
C210.096 (6)0.062 (4)0.040 (3)0.016 (4)0.016 (3)0.002 (3)
C220.032 (3)0.035 (3)0.037 (3)0.003 (2)0.005 (2)0.010 (2)
C230.033 (3)0.033 (3)0.032 (3)0.003 (2)0.000 (2)0.012 (2)
C240.022 (2)0.036 (3)0.038 (3)0.006 (2)0.0006 (19)0.014 (2)
C250.070 (4)0.043 (3)0.033 (3)0.014 (3)0.003 (3)0.011 (2)
C260.077 (5)0.054 (4)0.044 (3)0.017 (3)0.013 (3)0.027 (3)
C270.035 (3)0.033 (3)0.052 (3)0.004 (2)0.001 (2)0.018 (2)
C280.033 (3)0.037 (3)0.038 (3)0.005 (2)0.008 (2)0.006 (2)
C290.029 (3)0.040 (3)0.035 (3)0.006 (2)0.004 (2)0.014 (2)
C300.022 (2)0.028 (2)0.038 (3)0.0025 (19)0.0030 (19)0.010 (2)
C310.026 (2)0.029 (2)0.033 (2)0.0000 (19)0.0013 (19)0.017 (2)
C320.027 (2)0.030 (2)0.031 (2)0.0015 (19)0.0033 (19)0.013 (2)
C330.027 (2)0.037 (3)0.033 (2)0.006 (2)0.0027 (19)0.019 (2)
C340.034 (3)0.038 (3)0.044 (3)0.009 (2)0.007 (2)0.021 (2)
C350.041 (3)0.033 (3)0.038 (3)0.005 (2)0.007 (2)0.016 (2)
C360.034 (3)0.029 (3)0.033 (3)0.005 (2)0.002 (2)0.012 (2)
C370.056 (4)0.029 (3)0.047 (3)0.007 (2)0.006 (3)0.010 (2)
C380.080 (5)0.033 (3)0.068 (4)0.000 (3)0.012 (4)0.012 (3)
C390.092 (5)0.046 (4)0.042 (3)0.005 (3)0.002 (3)0.007 (3)
C400.062 (4)0.057 (4)0.077 (5)0.023 (3)0.006 (4)0.003 (4)
C410.029 (3)0.043 (3)0.039 (3)0.007 (2)0.000 (2)0.019 (2)
C420.019 (2)0.046 (3)0.033 (3)0.004 (2)0.0023 (19)0.013 (2)
C430.029 (3)0.047 (3)0.038 (3)0.006 (2)0.001 (2)0.013 (2)
C440.021 (2)0.057 (3)0.031 (3)0.009 (2)0.0002 (19)0.012 (2)
C450.019 (2)0.058 (3)0.036 (3)0.002 (2)0.002 (2)0.018 (2)
C460.020 (2)0.048 (3)0.030 (2)0.003 (2)0.0056 (19)0.009 (2)
C470.021 (2)0.048 (3)0.026 (2)0.005 (2)0.0005 (18)0.011 (2)
C480.035 (3)0.078 (4)0.037 (3)0.019 (3)0.008 (2)0.016 (3)
C490.105 (7)0.084 (6)0.087 (6)0.052 (5)0.052 (5)0.026 (5)
C500.028 (3)0.148 (8)0.057 (4)0.021 (4)0.007 (3)0.023 (4)
C510.050 (4)0.108 (6)0.036 (3)0.020 (4)0.006 (3)0.017 (3)
C520.020 (2)0.045 (3)0.033 (3)0.012 (2)0.0036 (19)0.008 (2)
C530.030 (3)0.059 (4)0.030 (3)0.009 (2)0.005 (2)0.006 (2)
C540.029 (3)0.044 (3)0.035 (3)0.011 (2)0.004 (2)0.007 (2)
C550.025 (2)0.032 (3)0.036 (3)0.002 (2)0.0001 (19)0.013 (2)
C560.042 (3)0.034 (3)0.054 (3)0.011 (2)0.009 (3)0.009 (3)
C570.056 (4)0.043 (3)0.067 (4)0.001 (3)0.022 (3)0.002 (3)
C580.031 (3)0.043 (3)0.061 (4)0.002 (2)0.013 (2)0.020 (3)
C590.034 (3)0.037 (3)0.054 (3)0.001 (2)0.003 (2)0.020 (3)
C600.028 (3)0.036 (3)0.039 (3)0.001 (2)0.004 (2)0.009 (2)
C610.084 (6)0.100 (7)0.130 (8)0.020 (5)0.011 (6)0.034 (6)
C620.047 (4)0.087 (6)0.120 (8)0.010 (4)0.001 (5)0.037 (5)
C630.185 (12)0.094 (7)0.062 (5)0.035 (7)0.026 (6)0.020 (5)
C640.081 (5)0.066 (5)0.069 (5)0.011 (4)0.007 (4)0.025 (4)
C650.035 (3)0.059 (4)0.054 (3)0.001 (3)0.002 (3)0.017 (3)
C660.036 (3)0.056 (4)0.073 (4)0.006 (3)0.008 (3)0.023 (3)
C670.129 (12)0.125 (11)0.26 (2)0.031 (10)0.045 (13)0.016 (12)
C680.087 (7)0.176 (11)0.104 (8)0.013 (7)0.002 (6)0.048 (8)
C1'0.13 (3)0.09 (3)0.021 (13)0.01 (2)0.019 (15)0.026 (16)
C2'0.08 (2)0.12 (3)0.060 (18)0.01 (2)0.017 (17)0.016 (18)
C3'0.058 (17)0.10 (2)0.053 (15)0.006 (15)0.007 (12)0.042 (15)
N10.055 (3)0.051 (3)0.078 (4)0.009 (3)0.030 (3)0.015 (3)
N20.060 (3)0.047 (3)0.069 (4)0.007 (2)0.010 (3)0.031 (3)
N30.069 (5)0.131 (7)0.135 (7)0.018 (5)0.009 (5)0.045 (6)
N40.083 (5)0.080 (5)0.131 (7)0.005 (4)0.042 (5)0.002 (5)
N50.127 (7)0.095 (6)0.071 (5)0.016 (5)0.011 (4)0.012 (4)
N60.32 (3)0.28 (2)0.72 (6)0.06 (2)0.35 (4)0.03 (3)
O10.0257 (18)0.0349 (19)0.044 (2)0.0021 (14)0.0061 (15)0.0038 (16)
O20.0300 (19)0.047 (2)0.0323 (18)0.0081 (16)0.0003 (14)0.0103 (16)
O30.0242 (17)0.045 (2)0.0286 (17)0.0003 (15)0.0019 (13)0.0086 (15)
O40.0203 (16)0.0319 (17)0.0329 (17)0.0002 (13)0.0004 (13)0.0083 (14)
O50.043 (2)0.0330 (19)0.0336 (18)0.0107 (16)0.0014 (15)0.0078 (15)
O60.0249 (17)0.0347 (19)0.0413 (19)0.0031 (14)0.0014 (14)0.0092 (15)
O70.169 (5)0.051 (2)0.073 (2)0.028 (2)0.019 (3)0.0238 (19)
O80.169 (5)0.051 (2)0.073 (2)0.028 (2)0.019 (3)0.0238 (19)
O90.063 (2)0.080 (3)0.137 (4)0.007 (2)0.051 (2)0.014 (3)
O100.063 (2)0.080 (3)0.137 (4)0.007 (2)0.051 (2)0.014 (3)
Geometric parameters (Å, º) top
C1—C41.580 (11)C38—H38B0.9600
C1—H1A0.9600C38—H38C0.9600
C1—H1B0.9600C39—H39A0.9600
C1—H1C0.9600C39—H39B0.9600
C2—C41.475 (12)C39—H39C0.9600
C2—H2A0.9600C40—H40A0.9600
C2—H2B0.9600C40—H40B0.9600
C2—H2C0.9600C40—H40C0.9600
C3—C41.550 (11)C41—C421.532 (7)
C3—H3A0.9600C41—H41A0.9700
C3—H3B0.9600C41—H41B0.9700
C3—H3C0.9600C42—C471.384 (7)
C4—C51.548 (7)C42—C431.404 (7)
C4—C2'1.5498 (11)C43—C441.409 (8)
C4—C1'1.5501 (11)C43—H430.9300
C4—C3'1.5501 (11)C44—C451.376 (8)
C5—C61.390 (8)C44—C481.543 (7)
C5—C101.415 (8)C45—C461.403 (7)
C6—C71.400 (7)C45—H450.9300
C6—H60.9300C46—C471.411 (7)
C7—C81.408 (7)C46—C521.523 (7)
C7—C521.531 (7)C47—O31.412 (5)
C8—O21.377 (5)C48—C491.517 (10)
C8—C91.400 (7)C48—C511.534 (9)
C9—C101.396 (7)C48—C501.547 (9)
C9—C111.532 (7)C49—H49A0.9600
C10—H100.9300C49—H49B0.9600
C11—C121.524 (7)C49—H49C0.9600
C11—H11A0.9700C50—H50A0.9600
C11—H11B0.9700C50—H50B0.9600
C12—C171.367 (7)C50—H50C0.9600
C12—C131.422 (7)C51—H51A0.9600
C13—O41.386 (5)C51—H51B0.9600
C13—C141.407 (7)C51—H51C0.9600
C14—C151.388 (7)C52—H52A0.9700
C14—C301.532 (7)C52—H52B0.9700
C15—C161.400 (7)C53—O31.438 (6)
C15—H150.9300C53—C541.504 (7)
C16—C171.413 (7)C53—H53A0.9700
C16—C181.529 (7)C53—H53B0.9700
C17—H170.9300C54—O61.431 (6)
C18—C211.524 (9)C54—H54A0.9700
C18—C191.544 (8)C54—H54B0.9700
C18—C201.567 (9)C55—O61.372 (5)
C19—H19A0.9600C55—C601.382 (7)
C19—H19B0.9600C55—C561.387 (7)
C19—H19C0.9600C56—C571.392 (8)
C20—H20A0.9600C56—H560.9300
C20—H20B0.9600C57—C581.371 (8)
C20—H20C0.9600C57—H570.9300
C21—H21A0.9600C58—C591.371 (8)
C21—H21B0.9600C58—N11.467 (7)
C21—H21C0.9600C59—C601.391 (7)
C22—O41.443 (5)C59—H590.9300
C22—C231.505 (7)C60—H600.9300
C22—H22A0.9700C61—C621.444 (13)
C22—H22B0.9700C61—H61A0.9600
C23—O51.434 (6)C61—H61B0.9600
C23—H23A0.9700C61—H61C0.9600
C23—H23B0.9700C62—N31.133 (11)
C24—O51.360 (6)C63—C641.436 (11)
C24—C291.385 (7)C63—H63A0.9600
C24—C251.405 (8)C63—H63B0.9600
C25—C261.378 (8)C63—H63C0.9600
C25—H250.9300C64—N51.121 (9)
C26—C271.383 (8)C65—C661.443 (9)
C26—H260.9300C65—H65A0.9600
C27—C281.383 (8)C65—H65B0.9600
C27—N21.463 (7)C65—H65C0.9600
C28—C291.378 (7)C66—N41.131 (9)
C28—H280.9300C67—N61.20 (3)
C29—H290.9300C67—C681.529 (18)
C30—C311.542 (7)C68—H68A0.9600
C30—H30A0.9700C68—H68B0.9600
C30—H30B0.9700C68—H68C0.9600
C31—C361.377 (7)C1'—H1'10.9600
C31—C321.417 (7)C1'—H1'20.9600
C32—O11.369 (5)C1'—H1'30.9600
C32—C331.396 (7)C2'—H2'10.9600
C33—C341.390 (7)C2'—H2'20.9600
C33—C411.545 (7)C2'—H2'30.9600
C34—C351.390 (8)C3'—H3'10.9600
C34—H340.9300C3'—H3'20.9600
C35—C361.417 (7)C3'—H3'30.9600
C35—C371.528 (7)N1—O91.202 (7)
C36—H360.9300N1—O101.210 (7)
C37—C381.534 (8)N2—O71.212 (7)
C37—C391.540 (9)N2—O81.222 (7)
C37—C401.546 (9)O1—H10.8200
C38—H38A0.9600O2—H20.8200
C4—C1—H1A109.5H38A—C38—H38C109.5
C4—C1—H1B109.5H38B—C38—H38C109.5
H1A—C1—H1B109.5C37—C39—H39A109.5
C4—C1—H1C109.5C37—C39—H39B109.5
H1A—C1—H1C109.5H39A—C39—H39B109.5
H1B—C1—H1C109.5C37—C39—H39C109.5
C4—C2—H2A109.5H39A—C39—H39C109.5
C4—C2—H2B109.5H39B—C39—H39C109.5
H2A—C2—H2B109.5C37—C40—H40A109.5
C4—C2—H2C109.5C37—C40—H40B109.5
H2A—C2—H2C109.5H40A—C40—H40B109.5
H2B—C2—H2C109.5C37—C40—H40C109.5
C4—C3—H3A109.5H40A—C40—H40C109.5
C4—C3—H3B109.5H40B—C40—H40C109.5
H3A—C3—H3B109.5C42—C41—C33111.6 (4)
C4—C3—H3C109.5C42—C41—H41A109.3
H3A—C3—H3C109.5C33—C41—H41A109.3
H3B—C3—H3C109.5C42—C41—H41B109.3
C2—C4—C5112.3 (6)C33—C41—H41B109.3
C2—C4—C3111.4 (8)H41A—C41—H41B108.0
C5—C4—C3107.2 (5)C47—C42—C43119.5 (5)
C2'—C4—C1'119.7 (19)C47—C42—C41121.5 (4)
C2'—C4—C3'109.6 (18)C43—C42—C41118.7 (5)
C1'—C4—C3'99 (2)C42—C43—C44120.4 (5)
C2—C4—C1112.0 (8)C42—C43—H43119.8
C5—C4—C1111.0 (5)C44—C43—H43119.8
C3—C4—C1102.3 (7)C45—C44—C43117.8 (4)
C6—C5—C10117.0 (5)C45—C44—C48120.3 (5)
C6—C5—C4122.9 (5)C43—C44—C48121.8 (5)
C10—C5—C4120.1 (5)C44—C45—C46124.2 (5)
C5—C6—C7122.9 (5)C44—C45—H45117.9
C5—C6—H6118.6C46—C45—H45117.9
C7—C6—H6118.6C45—C46—C47116.0 (5)
C6—C7—C8118.5 (5)C45—C46—C52121.1 (5)
C6—C7—C52119.7 (4)C47—C46—C52122.6 (4)
C8—C7—C52121.6 (4)C42—C47—C46122.1 (4)
O2—C8—C9122.2 (4)C42—C47—O3119.6 (4)
O2—C8—C7117.2 (4)C46—C47—O3118.3 (4)
C9—C8—C7120.6 (4)C49—C48—C51109.7 (6)
C10—C9—C8119.0 (5)C49—C48—C44112.5 (5)
C10—C9—C11118.9 (5)C51—C48—C44109.5 (5)
C8—C9—C11121.9 (4)C49—C48—C50109.1 (6)
C9—C10—C5122.1 (5)C51—C48—C50107.3 (6)
C9—C10—H10118.9C44—C48—C50108.6 (5)
C5—C10—H10118.9C48—C49—H49A109.5
C12—C11—C9110.4 (4)C48—C49—H49B109.5
C12—C11—H11A109.6H49A—C49—H49B109.5
C9—C11—H11A109.6C48—C49—H49C109.5
C12—C11—H11B109.6H49A—C49—H49C109.5
C9—C11—H11B109.6H49B—C49—H49C109.5
H11A—C11—H11B108.1C48—C50—H50A109.5
C17—C12—C13119.6 (4)C48—C50—H50B109.5
C17—C12—C11118.9 (5)H50A—C50—H50B109.5
C13—C12—C11121.2 (4)C48—C50—H50C109.5
O4—C13—C14122.8 (4)H50A—C50—H50C109.5
O4—C13—C12116.9 (4)H50B—C50—H50C109.5
C14—C13—C12120.3 (4)C48—C51—H51A109.5
C15—C14—C13117.5 (4)C48—C51—H51B109.5
C15—C14—C30118.2 (4)H51A—C51—H51B109.5
C13—C14—C30124.0 (4)C48—C51—H51C109.5
C14—C15—C16123.9 (5)H51A—C51—H51C109.5
C14—C15—H15118.0H51B—C51—H51C109.5
C16—C15—H15118.0C46—C52—C7111.0 (4)
C15—C16—C17116.4 (4)C46—C52—H52A109.4
C15—C16—C18124.0 (5)C7—C52—H52A109.4
C17—C16—C18119.5 (5)C46—C52—H52B109.4
C12—C17—C16122.1 (5)C7—C52—H52B109.4
C12—C17—H17118.9H52A—C52—H52B108.0
C16—C17—H17118.9O3—C53—C54106.3 (4)
C21—C18—C16112.0 (5)O3—C53—H53A110.5
C21—C18—C19109.1 (5)C54—C53—H53A110.5
C16—C18—C19109.3 (4)O3—C53—H53B110.5
C21—C18—C20108.3 (5)C54—C53—H53B110.5
C16—C18—C20109.2 (4)H53A—C53—H53B108.7
C19—C18—C20109.0 (5)O6—C54—C53106.7 (4)
C18—C19—H19A109.5O6—C54—H54A110.4
C18—C19—H19B109.5C53—C54—H54A110.4
H19A—C19—H19B109.5O6—C54—H54B110.4
C18—C19—H19C109.5C53—C54—H54B110.4
H19A—C19—H19C109.5H54A—C54—H54B108.6
H19B—C19—H19C109.5O6—C55—C60116.3 (4)
C18—C20—H20A109.5O6—C55—C56123.3 (4)
C18—C20—H20B109.5C60—C55—C56120.4 (4)
H20A—C20—H20B109.5C55—C56—C57119.0 (5)
C18—C20—H20C109.5C55—C56—H56120.5
H20A—C20—H20C109.5C57—C56—H56120.5
H20B—C20—H20C109.5C58—C57—C56120.0 (5)
C18—C21—H21A109.5C58—C57—H57120.0
C18—C21—H21B109.5C56—C57—H57120.0
H21A—C21—H21B109.5C57—C58—C59121.5 (5)
C18—C21—H21C109.5C57—C58—N1119.5 (5)
H21A—C21—H21C109.5C59—C58—N1118.9 (5)
H21B—C21—H21C109.5C58—C59—C60118.9 (5)
O4—C22—C23109.3 (4)C58—C59—H59120.6
O4—C22—H22A109.8C60—C59—H59120.6
C23—C22—H22A109.8C55—C60—C59120.2 (5)
O4—C22—H22B109.8C55—C60—H60119.9
C23—C22—H22B109.8C59—C60—H60119.9
H22A—C22—H22B108.3C62—C61—H61A109.5
O5—C23—C22108.5 (4)C62—C61—H61B109.5
O5—C23—H23A110.0H61A—C61—H61B109.5
C22—C23—H23A110.0C62—C61—H61C109.5
O5—C23—H23B110.0H61A—C61—H61C109.5
C22—C23—H23B110.0H61B—C61—H61C109.5
H23A—C23—H23B108.4N3—C62—C61179.9 (13)
O5—C24—C29124.8 (5)C64—C63—H63A109.5
O5—C24—C25116.2 (4)C64—C63—H63B109.5
C29—C24—C25119.0 (5)H63A—C63—H63B109.5
C26—C25—C24121.3 (5)C64—C63—H63C109.5
C26—C25—H25119.3H63A—C63—H63C109.5
C24—C25—H25119.3H63B—C63—H63C109.5
C25—C26—C27118.7 (6)N5—C64—C63178.7 (9)
C25—C26—H26120.7C66—C65—H65A109.5
C27—C26—H26120.7C66—C65—H65B109.5
C28—C27—C26120.5 (5)H65A—C65—H65B109.5
C28—C27—N2120.2 (5)C66—C65—H65C109.5
C26—C27—N2119.4 (5)H65A—C65—H65C109.5
C29—C28—C27121.0 (5)H65B—C65—H65C109.5
C29—C28—H28119.5N4—C66—C65179.3 (8)
C27—C28—H28119.5N6—C67—C68165 (3)
C28—C29—C24119.5 (5)C67—C68—H68A109.5
C28—C29—H29120.2C67—C68—H68B109.5
C24—C29—H29120.2H68A—C68—H68B109.5
C14—C30—C31111.1 (4)C67—C68—H68C109.5
C14—C30—H30A109.4H68A—C68—H68C109.5
C31—C30—H30A109.4H68B—C68—H68C109.5
C14—C30—H30B109.4C4—C1'—H1'1109.5
C31—C30—H30B109.4C4—C1'—H1'2109.5
H30A—C30—H30B108.0H1'1—C1'—H1'2109.5
C36—C31—C32118.1 (4)C4—C1'—H1'3109.5
C36—C31—C30121.3 (4)H1'1—C1'—H1'3109.5
C32—C31—C30120.4 (4)H1'2—C1'—H1'3109.5
O1—C32—C33124.6 (4)C4—C2'—H2'1109.5
O1—C32—C31115.0 (4)C4—C2'—H2'2109.5
C33—C32—C31120.4 (4)H2'1—C2'—H2'2109.5
C34—C33—C32119.5 (5)C4—C2'—H2'3109.5
C34—C33—C41118.5 (4)H2'1—C2'—H2'3109.5
C32—C33—C41121.9 (4)H2'2—C2'—H2'3109.5
C35—C34—C33121.9 (5)C4—C3'—H3'1109.5
C35—C34—H34119.1C4—C3'—H3'2109.5
C33—C34—H34119.1H3'1—C3'—H3'2109.5
C34—C35—C36117.2 (5)C4—C3'—H3'3109.5
C34—C35—C37123.2 (5)H3'1—C3'—H3'3109.5
C36—C35—C37119.6 (5)H3'2—C3'—H3'3109.5
C31—C36—C35122.8 (5)O9—N1—O10120.8 (5)
C31—C36—H36118.6O9—N1—C58120.6 (5)
C35—C36—H36118.6O10—N1—C58118.5 (5)
C35—C37—C38109.5 (4)O7—N2—O8121.7 (6)
C35—C37—C39109.6 (5)O7—N2—C27118.6 (5)
C38—C37—C39108.9 (5)O8—N2—C27119.7 (5)
C35—C37—C40112.1 (5)C32—O1—H1109.5
C38—C37—C40108.4 (5)C8—O2—H2109.5
C39—C37—C40108.2 (5)C47—O3—C53113.8 (4)
C37—C38—H38A109.5C13—O4—C22117.7 (3)
C37—C38—H38B109.5C24—O5—C23119.7 (4)
H38A—C38—H38B109.5C55—O6—C54119.8 (4)
C37—C38—H38C109.5
C2—C4—C5—C6123.5 (9)C31—C32—C33—C41178.4 (4)
C3—C4—C5—C6113.8 (7)C32—C33—C34—C351.5 (7)
C2'—C4—C5—C659.9 (16)C41—C33—C34—C35178.0 (5)
C1'—C4—C5—C6164.7 (18)C33—C34—C35—C360.4 (7)
C3'—C4—C5—C657.7 (14)C33—C34—C35—C37179.1 (5)
C1—C4—C5—C62.8 (8)C32—C31—C36—C351.3 (7)
C2—C4—C5—C1058.5 (9)C30—C31—C36—C35173.5 (4)
C3—C4—C5—C1064.2 (8)C34—C35—C36—C311.9 (7)
C2'—C4—C5—C10118.1 (15)C37—C35—C36—C31177.7 (4)
C1'—C4—C5—C1017.3 (19)C34—C35—C37—C38116.4 (6)
C3'—C4—C5—C10124.2 (13)C36—C35—C37—C3864.1 (7)
C1—C4—C5—C10175.2 (6)C34—C35—C37—C39124.1 (6)
C10—C5—C6—C70.8 (8)C36—C35—C37—C3955.4 (7)
C4—C5—C6—C7177.3 (5)C34—C35—C37—C403.9 (8)
C5—C6—C7—C80.7 (7)C36—C35—C37—C40175.6 (5)
C5—C6—C7—C52174.2 (5)C34—C33—C41—C4290.1 (5)
C6—C7—C8—O2177.2 (4)C32—C33—C41—C4286.3 (5)
C52—C7—C8—O28.0 (7)C33—C41—C42—C4791.5 (5)
C6—C7—C8—C90.0 (7)C33—C41—C42—C4382.6 (5)
C52—C7—C8—C9174.8 (4)C47—C42—C43—C440.3 (7)
O2—C8—C9—C10177.6 (4)C41—C42—C43—C44174.6 (4)
C7—C8—C9—C100.5 (7)C42—C43—C44—C451.9 (7)
O2—C8—C9—C117.8 (7)C42—C43—C44—C48178.8 (5)
C7—C8—C9—C11175.1 (4)C43—C44—C45—C461.8 (8)
C8—C9—C10—C50.3 (7)C48—C44—C45—C46178.9 (5)
C11—C9—C10—C5175.1 (4)C44—C45—C46—C470.1 (7)
C6—C5—C10—C90.3 (7)C44—C45—C46—C52173.2 (4)
C4—C5—C10—C9177.9 (5)C43—C42—C47—C461.4 (7)
C10—C9—C11—C1286.4 (5)C41—C42—C47—C46172.7 (4)
C8—C9—C11—C1288.2 (5)C43—C42—C47—O3179.2 (4)
C9—C11—C12—C1782.2 (5)C41—C42—C47—O35.1 (7)
C9—C11—C12—C1390.9 (5)C45—C46—C47—C421.5 (7)
C17—C12—C13—O4178.8 (4)C52—C46—C47—C42171.5 (4)
C11—C12—C13—O45.7 (6)C45—C46—C47—O3179.3 (4)
C17—C12—C13—C140.0 (7)C52—C46—C47—O36.3 (7)
C11—C12—C13—C14173.0 (4)C45—C44—C48—C49173.3 (6)
O4—C13—C14—C15179.0 (4)C43—C44—C48—C496.0 (8)
C12—C13—C14—C150.4 (6)C45—C44—C48—C5151.1 (7)
O4—C13—C14—C305.2 (7)C43—C44—C48—C51128.2 (6)
C12—C13—C14—C30173.5 (4)C45—C44—C48—C5065.8 (7)
C13—C14—C15—C161.0 (7)C43—C44—C48—C50114.9 (6)
C30—C14—C15—C16175.2 (4)C45—C46—C52—C774.4 (5)
C14—C15—C16—C172.5 (7)C47—C46—C52—C798.3 (5)
C14—C15—C16—C18179.6 (4)C6—C7—C52—C4678.2 (5)
C13—C12—C17—C161.6 (7)C8—C7—C52—C4696.5 (5)
C11—C12—C17—C16174.9 (4)O3—C53—C54—O662.0 (6)
C15—C16—C17—C122.8 (7)O6—C55—C56—C57177.3 (6)
C18—C16—C17—C12179.2 (4)C60—C55—C56—C571.6 (9)
C15—C16—C18—C215.0 (8)C55—C56—C57—C580.7 (10)
C17—C16—C18—C21177.2 (5)C56—C57—C58—C590.0 (11)
C15—C16—C18—C19116.0 (6)C56—C57—C58—N1177.4 (6)
C17—C16—C18—C1961.9 (7)C57—C58—C59—C600.2 (9)
C15—C16—C18—C20124.9 (5)N1—C58—C59—C60177.6 (6)
C17—C16—C18—C2057.3 (6)O6—C55—C60—C59177.2 (5)
O4—C22—C23—O565.7 (5)C56—C55—C60—C591.8 (8)
O5—C24—C25—C26179.5 (5)C58—C59—C60—C551.1 (8)
C29—C24—C25—C260.8 (9)C57—C58—N1—O9173.1 (7)
C24—C25—C26—C270.2 (10)C59—C58—N1—O94.3 (10)
C25—C26—C27—C280.1 (9)C57—C58—N1—O109.2 (10)
C25—C26—C27—N2178.8 (6)C59—C58—N1—O10173.4 (7)
C26—C27—C28—C291.4 (8)C28—C27—N2—O79.7 (9)
N2—C27—C28—C29179.9 (5)C26—C27—N2—O7169.0 (7)
C27—C28—C29—C242.5 (7)C28—C27—N2—O8173.7 (6)
O5—C24—C29—C28179.3 (5)C26—C27—N2—O87.6 (9)
C25—C24—C29—C282.1 (7)C42—C47—O3—C5390.6 (5)
C15—C14—C30—C3174.8 (5)C46—C47—O3—C5391.6 (5)
C13—C14—C30—C3199.0 (5)C54—C53—O3—C47178.3 (4)
C14—C30—C31—C3685.5 (5)C14—C13—O4—C2262.0 (6)
C14—C30—C31—C3289.2 (5)C12—C13—O4—C22119.3 (4)
C36—C31—C32—O1179.7 (4)C23—C22—O4—C13133.4 (4)
C30—C31—C32—O15.5 (6)C29—C24—O5—C239.1 (7)
C36—C31—C32—C330.7 (7)C25—C24—O5—C23169.5 (5)
C30—C31—C32—C33175.6 (4)C22—C23—O5—C24180.0 (4)
O1—C32—C33—C34179.1 (4)C60—C55—O6—C54166.9 (4)
C31—C32—C33—C342.1 (7)C56—C55—O6—C5414.2 (7)
O1—C32—C33—C412.7 (7)C53—C54—O6—C55177.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.821.992.802 (6)171
O2—H2···O40.821.972.781 (4)176
C50—H50C···O7i0.962.593.487 (10)156
C68—H68B···O100.962.393.247 (13)148
C65—H65A···Cg10.962.663.590 (6)163
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC60H70N2O10·4C2H3N
Mr1143.40
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)13.195 (3), 13.388 (3), 19.692 (5)
α, β, γ (°)71.978 (3), 84.022 (3), 82.230 (3)
V3)3270.5 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.51 × 0.35 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15816, 11155, 7114
Rint0.049
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.114, 0.349, 1.05
No. of reflections11155
No. of parameters775
No. of restraints5
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.78, 0.64

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.821.992.802 (6)171
O2—H2···O40.821.972.781 (4)176
C50—H50C···O7i0.962.593.487 (10)156
C68—H68B···O100.962.393.247 (13)148
C65—H65A···Cg10.962.663.590 (6)163
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

Financial support from the National Natural Science Foundation of China (grant No. 20572064) and the Natural Science Foundation of Shandong Province, China (grant No. Y2006B30) is gratefully acknowledged.

References

First citationBöhmer, V., Ferguson, G., Gallagher, J. F., Lough, A. J., McKervey, M. A., Madigan, E., Moran, M. B., Phillips, J. & Williams, J. (1993). J. Chem. Soc. Perkin Trans. 1, pp. 1521–1527.  Google Scholar
First citationBolte, M., Danila, C. & Böhmer, V. (2003). Acta Cryst. E59, o533–o534.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBugge, K.-E., Verboom, W., Reinhoudt, D. N. & Harkema, S. (1992). Acta Cryst. C48, 1848–1851.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationDrew, M. G. B., Beer, P. D. & Ogden, M. I. (1997). Acta Cryst. C53, 472–474.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationGale, P. A., Chen, Z., Drew, M. G. B., Heath, J. A. & Beer, P. D. (1998). Polyhedron, 17, 405–412.  Web of Science CSD CrossRef CAS Google Scholar
First citationGutsche, C. D. (1998). Calixarenes Revisited. RSC Monographs in Chemistry. Cambridge: Royal Society of Chemistry.  Google Scholar
First citationMcKervey, M. A., Seward, E. M., Ferguson, G. & Ruhl, B. L. (1986). J. Org. Chem. 51, 3581–3584.  CSD CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSingh, N., Kumar, M. & Hundal, G. (2004). Tetrahedron 60, 5393–5405.  Web of Science CSD CrossRef CAS Google Scholar
First citationTsuzuki, S., Honda, K., Uchimaru, T., Mikami, M. & Tanabe, K. (2000). J. Am. Chem. Soc. 122, 3746–3753.  Web of Science CrossRef CAS Google Scholar
First citationUmezawa, Y., Tsuboyama, S., Honda, K., Uzawa, J. & Nishio, M. (1998). Bull. Chem. Soc. Jpn, 71, 1207–1213.  Web of Science CrossRef CAS Google Scholar
First citationZeng, X.-S., Weng, L.-H., Chen, L.-X., Xu, F.-B., Li, Q.-S., Leng, X.-B., He, X.-W. & Zhang, Z.-Z. (2002). Tetrahedron, 58, 2647–2658.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 6| June 2009| Pages o1336-o1337
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds