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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1336–o1337.
Published online 2009 May 20. doi:  10.1107/S1600536809018212
PMCID: PMC2969685

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

Abstract

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 [triangle]). For related crystal structures, see: Singh et al. (2004 [triangle]); Bolte et al. (2003 [triangle]); Zeng et al. (2002 [triangle]); Gale et al. (1998 [triangle]); Drew et al. (1997 [triangle]); Böhmer et al. (1993 [triangle]); Bugge et al. (1992 [triangle]). For C—H(...)π contacts, see: Tsuzuki et al. (2000 [triangle]); Umezawa et al. (1998 [triangle]). For inclusion complexes, see: McKervey et al. (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1336-scheme1.jpg

Experimental

Crystal data

  • C60H70N2O10·4C2H3N
  • M r = 1143.40
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1336-efi1.jpg
  • 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)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.114
  • wR(F 2) = 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

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018212/xu2512sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018212/xu2512Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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.

Crystal data

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

Bruker SMART CCD area-detector diffractometer7114 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
graphiteθmax = 25.0°, θmin = 1.6°
[var phi] and ω scansh = −15→15
15816 measured reflectionsk = −15→15
11155 independent reflectionsl = −13→23

Refinement

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 = 1.05w = 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

Special details

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)

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)
H150.8274−0.03030.79320.038*
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*
H19C0.6494−0.00290.94000.093*
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)
H21A0.7986−0.11930.90730.107*
H21B0.8476−0.12000.97660.107*
H21C0.9101−0.08830.90240.107*
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)
H30A0.8727−0.01780.66520.035*
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)
H340.4806−0.15920.68050.044*
C350.6199 (4)−0.1770 (4)0.7186 (3)0.0370 (12)
C360.7094 (4)−0.1248 (4)0.7083 (3)0.0324 (11)
H360.7644−0.15810.73580.039*
C370.6147 (5)−0.2837 (4)0.7760 (3)0.0445 (14)
C380.6961 (6)−0.3656 (5)0.7568 (4)0.0629 (19)
H38A0.6818−0.37450.71230.094*
H38B0.6947−0.43190.79380.094*
H38C0.7626−0.34170.75220.094*
C390.6358 (6)−0.2736 (5)0.8489 (3)0.0618 (18)
H39A0.7029−0.25190.84610.093*
H39B0.6321−0.34060.88490.093*
H39C0.5855−0.22190.86110.093*
C400.5086 (5)−0.3241 (6)0.7832 (4)0.068 (2)
H40A0.4562−0.27150.79180.103*
H40B0.5065−0.38790.82250.103*
H40C0.4971−0.33820.73990.103*
C410.4530 (4)0.0235 (4)0.5799 (3)0.0356 (12)
H41A0.47640.06570.53270.043*
H41B0.4163−0.03110.57410.043*
C420.3802 (3)0.0938 (4)0.6162 (3)0.0323 (11)
C430.3087 (4)0.0466 (4)0.6706 (3)0.0380 (12)
H430.3024−0.02500.68120.046*
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)
H49A0.1507−0.07580.74320.138*
H49B0.1237−0.08800.82460.138*
H49C0.2385−0.09220.79460.138*
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)

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, °)

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—C6−123.5 (9)C31—C32—C33—C41178.4 (4)
C3—C4—C5—C6113.8 (7)C32—C33—C34—C35−1.5 (7)
C2'—C4—C5—C659.9 (16)C41—C33—C34—C35−178.0 (5)
C1'—C4—C5—C6−164.7 (18)C33—C34—C35—C36−0.4 (7)
C3'—C4—C5—C6−57.7 (14)C33—C34—C35—C37179.1 (5)
C1—C4—C5—C62.8 (8)C32—C31—C36—C35−1.3 (7)
C2—C4—C5—C1058.5 (9)C30—C31—C36—C35173.5 (4)
C3—C4—C5—C10−64.2 (8)C34—C35—C36—C311.9 (7)
C2'—C4—C5—C10−118.1 (15)C37—C35—C36—C31−177.7 (4)
C1'—C4—C5—C1017.3 (19)C34—C35—C37—C38116.4 (6)
C3'—C4—C5—C10124.2 (13)C36—C35—C37—C38−64.1 (7)
C1—C4—C5—C10−175.2 (6)C34—C35—C37—C39−124.1 (6)
C10—C5—C6—C70.8 (8)C36—C35—C37—C3955.4 (7)
C4—C5—C6—C7−177.3 (5)C34—C35—C37—C40−3.9 (8)
C5—C6—C7—C8−0.7 (7)C36—C35—C37—C40175.6 (5)
C5—C6—C7—C52174.2 (5)C34—C33—C41—C4290.1 (5)
C6—C7—C8—O2−177.2 (4)C32—C33—C41—C42−86.3 (5)
C52—C7—C8—O28.0 (7)C33—C41—C42—C4791.5 (5)
C6—C7—C8—C90.0 (7)C33—C41—C42—C43−82.6 (5)
C52—C7—C8—C9−174.8 (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—C45−1.9 (7)
O2—C8—C9—C11−7.8 (7)C42—C43—C44—C48178.8 (5)
C7—C8—C9—C11175.1 (4)C43—C44—C45—C461.8 (8)
C8—C9—C10—C5−0.3 (7)C48—C44—C45—C46−178.9 (5)
C11—C9—C10—C5−175.1 (4)C44—C45—C46—C47−0.1 (7)
C6—C5—C10—C9−0.3 (7)C44—C45—C46—C52−173.2 (4)
C4—C5—C10—C9177.9 (5)C43—C42—C47—C461.4 (7)
C10—C9—C11—C1286.4 (5)C41—C42—C47—C46−172.7 (4)
C8—C9—C11—C12−88.2 (5)C43—C42—C47—O3179.2 (4)
C9—C11—C12—C17−82.2 (5)C41—C42—C47—O35.1 (7)
C9—C11—C12—C1390.9 (5)C45—C46—C47—C42−1.5 (7)
C17—C12—C13—O4178.8 (4)C52—C46—C47—C42171.5 (4)
C11—C12—C13—O45.7 (6)C45—C46—C47—O3−179.3 (4)
C17—C12—C13—C140.0 (7)C52—C46—C47—O3−6.3 (7)
C11—C12—C13—C14−173.0 (4)C45—C44—C48—C49−173.3 (6)
O4—C13—C14—C15−179.0 (4)C43—C44—C48—C496.0 (8)
C12—C13—C14—C15−0.4 (6)C45—C44—C48—C51−51.1 (7)
O4—C13—C14—C30−5.2 (7)C43—C44—C48—C51128.2 (6)
C12—C13—C14—C30173.5 (4)C45—C44—C48—C5065.8 (7)
C13—C14—C15—C16−1.0 (7)C43—C44—C48—C50−114.9 (6)
C30—C14—C15—C16−175.2 (4)C45—C46—C52—C774.4 (5)
C14—C15—C16—C172.5 (7)C47—C46—C52—C7−98.3 (5)
C14—C15—C16—C18−179.6 (4)C6—C7—C52—C46−78.2 (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—C12−2.8 (7)O6—C55—C56—C57−177.3 (6)
C18—C16—C17—C12179.2 (4)C60—C55—C56—C571.6 (9)
C15—C16—C18—C215.0 (8)C55—C56—C57—C58−0.7 (10)
C17—C16—C18—C21−177.2 (5)C56—C57—C58—C590.0 (11)
C15—C16—C18—C19−116.0 (6)C56—C57—C58—N1177.4 (6)
C17—C16—C18—C1961.9 (7)C57—C58—C59—C60−0.2 (9)
C15—C16—C18—C20124.9 (5)N1—C58—C59—C60−177.6 (6)
C17—C16—C18—C20−57.3 (6)O6—C55—C60—C59177.2 (5)
O4—C22—C23—O565.7 (5)C56—C55—C60—C59−1.8 (8)
O5—C24—C25—C26−179.5 (5)C58—C59—C60—C551.1 (8)
C29—C24—C25—C26−0.8 (9)C57—C58—N1—O9−173.1 (7)
C24—C25—C26—C27−0.2 (10)C59—C58—N1—O94.3 (10)
C25—C26—C27—C28−0.1 (9)C57—C58—N1—O109.2 (10)
C25—C26—C27—N2−178.8 (6)C59—C58—N1—O10−173.4 (7)
C26—C27—C28—C291.4 (8)C28—C27—N2—O7−9.7 (9)
N2—C27—C28—C29−179.9 (5)C26—C27—N2—O7169.0 (7)
C27—C28—C29—C24−2.5 (7)C28—C27—N2—O8173.7 (6)
O5—C24—C29—C28−179.3 (5)C26—C27—N2—O8−7.6 (9)
C25—C24—C29—C282.1 (7)C42—C47—O3—C5390.6 (5)
C15—C14—C30—C3174.8 (5)C46—C47—O3—C53−91.6 (5)
C13—C14—C30—C31−99.0 (5)C54—C53—O3—C47−178.3 (4)
C14—C30—C31—C36−85.5 (5)C14—C13—O4—C22−62.0 (6)
C14—C30—C31—C3289.2 (5)C12—C13—O4—C22119.3 (4)
C36—C31—C32—O1−179.7 (4)C23—C22—O4—C13−133.4 (4)
C30—C31—C32—O15.5 (6)C29—C24—O5—C23−9.1 (7)
C36—C31—C32—C33−0.7 (7)C25—C24—O5—C23169.5 (5)
C30—C31—C32—C33−175.6 (4)C22—C23—O5—C24180.0 (4)
O1—C32—C33—C34−179.1 (4)C60—C55—O6—C54166.9 (4)
C31—C32—C33—C342.1 (7)C56—C55—O6—C54−14.2 (7)
O1—C32—C33—C41−2.7 (7)C53—C54—O6—C55−177.4 (4)

Hydrogen-bond geometry (Å, °)

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 codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2512).

References

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