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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 2| February 2010| Pages o419-o420
https://doi.org/10.1107/S1600536810002242

25,26,27,28-Tetra­propoxycalix[4]arene-5,17-dicarbo­nitrile

Jan Budka,a Václav Eigner,b Roman Holakovský,a* Petr Kovaříčeka and Tereza Loužilováa

aDepartment of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28, Prague 6, Czech Republic, and bDepartment of Solid State Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28, Prague 6, Czech Republic
*Correspondence e-mail: Roman.Holakovsky@vscht.cz

(Received 9 December 2009; accepted 18 January 2010; online 23 January 2010)

In the title compound, C42H46N2O4, both crystallographically independent mol­ecules display a 1,3-alternate conformation. Their crystal packing is stabilized by non-classical C—H⋯N hydrogen bonds. The dihedral angles between the planes of the aromatic rings and the mean plane through the methyl­ene C atoms bridging the aromatic rings are 78.10 (13), 80.74 (14), 81.89 (12) and 79.05 (14)° for the first mol­ecule, and 71.65 (11), 76.60 (13), 77.97 (14) and 74.76 (13)° for the second mol­ecule. Both mol­ecules have three C atoms of one prop­oxy chain disordered over two set of sites; the site-occupancy factors are 0.7/0.3 and 0.6/0.4, respectively.

Related literature

For calix[4]arene derivatives and their uses as supra­molecular building blocks, see: Gutsche (2008[Gutsche, C. D. (2008). Calixarenes: An Introduction, 2nd ed., Monographs in Supramolecular Chemistry, edited by J. F. Stoddart, Cambridge: The Royal Society of Chemistry.]); Rao & Dey (2004[Rao, C. P. & Dey, M. (2004). Calixarenes, Encyclopedia of Nanoscience and Nanotechnology, vol. 1, 475-497. Stevenson Ranch, California: American Scientific Publishers.]). For applications of the title compound, see: Pinkhassik et al. (1997[Pinkhassik, E., Stibor, I., Casnati, A. & Ungaro, R. (1997). J. Org. Chem. 62, 8654-8659.]; 1998[Pinkhassik, E., Sidorov, V. & Stibor, I. (1998). J. Org. Chem. 63, 9644-9651.]). For details of the synthesis, see: Sýkora et al. (2005[Sýkora, J., Budka, J., Lhoták, P., Stibor, I. & Císařová, I. (2005). Org. Biomol. Chem. 3, 2572-2578.]); Casnati et al. (1996[Casnati, A., Fochi, M., Minari, P., Pochini, A., Reggiani, M. & Ungaro, R. (1996). Gazz. Chim. Ital. 124, 99-106.]). For the weighting scheme, see: Prince (1982[Prince, E. (1982). Mathematical Techniques in Crystallography and Materials Science. New York: Springer-Verlag.]); Watkin (1994[Watkin, D. (1994). Acta Cryst. A50, 411-437.]).

[Scheme 1]

Experimental

Crystal data

  • C42H46N2O4

  • Mr = 642.84

  • Monoclinic, P 21 /n

  • a = 19.398 (4) Å

  • b = 10.6491 (12) Å

  • c = 34.391 (2) Å

  • β = 93.987 (10)°

  • V = 7086.9 (16) Å3

  • Z = 8

  • Cu Kα radiation

  • μ = 0.61 mm−1

  • T = 150 K

  • 0.40 × 0.33 × 0.12 mm
Data collection

  • Oxford Diffraction XCALIBUR diffractometer

  • Absorption correction: analytical (de Meulenaer & Tompa, 1965[Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014-1018.]) Tmin = 0.83, Tmax = 0.93

  • 44656 measured reflections

  • 14658 independent reflections

  • 7906 reflections with I > 2σ(I)

  • Rint = 0.103
Refinement

  • R[F2 > 2σ(F2)] = 0.083

  • wR(F2) = 0.063

  • S = 1.10

  • 7906 reflections

  • 920 parameters

  • 18 restraints

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.41 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C10—H101⋯N30i 0.95 2.55 3.392 (8) 147
Symmetry code: (i) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2002[Oxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2002[Oxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003[Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.]); molecular graphics: CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: CRYSTALS.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810002242/om2307sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002242/om2307Isup2.hkl

checkCIF report


Comment top

Calix[4]arene is one of the most important molecular scaffolds used for preparation of structurally well defined ligands (Gutsche, 2008; Rao & Dey, 2004). Calix[4]arene in 1,3 alternate conformation bearing two nitrile groups was prepared from appropriate bromo derivative (Sýkora et al., 2005) by heating with CuCN in N-methylpyrrolidone (Casnati et al., 1996). Such molecules can be used as a starting material for preparation of ligands for recognition of neutral molecules (Pinkhassik et al., 1998) or neutral molecules and silver cation (Pinkhassik et al., 1997).

The title compound adopts 1,3-alternate conformation (Fig. 1) with all phenolic rings pitched away from the calix cavity, as defined by the angles which the aromatic rings make with the plane of the four bridging methylenes 78.10 (13), 80.74 (14), 81.89 (12) and 79.05 (14)° for the first and 71.65 (11), 76.60 (13), 77.97 (14) and 74.76 (13)° for the second molecule. Two opposite rings make interplanar angle of 20.03 (15) and 20.21 (18)° for the first molecule and 30.38 (18) and 28.64 (16)° for the second.

In the crystal structure there are non-classical intermolecular hydrogen bonds (Table 1).

Related literature top

For calix[4]arene derivatives and their uses as supramolecular building blocks, see: Gutsche (2008); Rao & Dey (2004). For applications of the title compound, see: Pinkhassik et al. (1997; 1998). For details of the synthesis, see: Sýkora et al. (2005); Casnati et al. (1996). For the weighting scheme, see: Prince (1982); Watkin (1994).

Experimental top

A mixture of 5,17-dibromo-25,26,27,28-tetrapropoxycalix[4]arene (1 g, 1.33 mmol) and CuCN (0.48 g, 5.32 mmol) in N-methylpyrrolidone (20 ml) was refluxed for 5 h and cooled to 373 K. Then reaction was quenched by careful addition of a solution of FeCl3 (4.32 g, 26.64 mmol) in HCl (2 M, 30 ml) and resulting mixture was refluxed for 1 h. Reaction mixture was filtrated and filtration cake was washed by methanol. The solvent was removed under reduced pressure and the residue was purified by chromatography (silica gel, dichloromethane) to give the title compound as a white solid (38% yield). Crystals of the title compound suitable for X-ray diffraction were obtained by recrystallization from pentan-1-ol.

Refinement top

In the absence of significant anomalous scattering, Friedel pairs were merged.

The H atoms were positioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C—H in the range 0.93–0.98 = 0.82 Å) and Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom), after which the positions were refined with riding constraints.

Structure description top

Calix[4]arene is one of the most important molecular scaffolds used for preparation of structurally well defined ligands (Gutsche, 2008; Rao & Dey, 2004). Calix[4]arene in 1,3 alternate conformation bearing two nitrile groups was prepared from appropriate bromo derivative (Sýkora et al., 2005) by heating with CuCN in N-methylpyrrolidone (Casnati et al., 1996). Such molecules can be used as a starting material for preparation of ligands for recognition of neutral molecules (Pinkhassik et al., 1998) or neutral molecules and silver cation (Pinkhassik et al., 1997).

The title compound adopts 1,3-alternate conformation (Fig. 1) with all phenolic rings pitched away from the calix cavity, as defined by the angles which the aromatic rings make with the plane of the four bridging methylenes 78.10 (13), 80.74 (14), 81.89 (12) and 79.05 (14)° for the first and 71.65 (11), 76.60 (13), 77.97 (14) and 74.76 (13)° for the second molecule. Two opposite rings make interplanar angle of 20.03 (15) and 20.21 (18)° for the first molecule and 30.38 (18) and 28.64 (16)° for the second.

In the crystal structure there are non-classical intermolecular hydrogen bonds (Table 1).

For calix[4]arene derivatives and their uses as supramolecular building blocks, see: Gutsche (2008); Rao & Dey (2004). For applications of the title compound, see: Pinkhassik et al. (1997; 1998). For details of the synthesis, see: Sýkora et al. (2005); Casnati et al. (1996). For the weighting scheme, see: Prince (1982); Watkin (1994).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003).

Figures top
[Figure 1] Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.
25,26,27,28-Tetrapropoxycalix[4]arene-5,17-dicarbonitrile top
Crystal data top
C42H46N2O4F(000) = 2752
Mr = 642.84Dx = 1.205 Mg m−3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 19.398 (4) ÅCell parameters from 3818 reflections
b = 10.6491 (12) Åθ = 4–78°
c = 34.391 (2) ŵ = 0.61 mm−1
β = 93.987 (10)°T = 150 K
V = 7086.9 (16) Å3Block, colorless
Z = 80.40 × 0.33 × 0.12 mm
Data collection top
Oxford Diffraction XCALIBUR
diffractometer		14658 independent reflections
Graphite monochromator7906 reflections with I > 2σ(I)
Detector resolution: 8.1917 pixels mm-1Rint = 0.103
φ & ω scansθmax = 78.0°, θmin = 4.4°
Absorption correction: analytical
(de Meulenaer & Tompa, 1965)		h = −24→24
Tmin = 0.83, Tmax = 0.93k = −13→10
44656 measured reflectionsl = −43→43
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.083H-atom parameters constrained
wR(F2) = 0.063 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A0*T0(x) + A1*T1(x) ··· + An-1]*Tn-1(x)]
where Ai are the Chebychev coefficients listed below and x = F /Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)2]2 Ai are: 20.7 2.42 17.0 5.57
S = 1.10(Δ/σ)max = 0.025
7906 reflectionsΔρmax = 0.38 e Å−3
920 parametersΔρmin = −0.41 e Å−3
18 restraints
Crystal data top
C42H46N2O4V = 7086.9 (16) Å3
Mr = 642.84Z = 8
Monoclinic, P21/nCu Kα radiation
a = 19.398 (4) ŵ = 0.61 mm−1
b = 10.6491 (12) ÅT = 150 K
c = 34.391 (2) Å0.40 × 0.33 × 0.12 mm
β = 93.987 (10)°
Data collection top
Oxford Diffraction XCALIBUR
diffractometer		14658 independent reflections
Absorption correction: analytical
(de Meulenaer & Tompa, 1965)		7906 reflections with I > 2σ(I)
Tmin = 0.83, Tmax = 0.93Rint = 0.103
44656 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.08318 restraints
wR(F2) = 0.063H-atom parameters constrained
S = 1.10Δρmax = 0.38 e Å−3
7906 reflectionsΔρmin = −0.41 e Å−3
920 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1 K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1−0.16556 (18)0.4376 (3)0.23298 (9)0.0275
C2−0.18252 (17)0.3717 (3)0.27001 (9)0.0311
C3−0.12130 (17)0.3503 (3)0.29917 (8)0.0271
C4−0.10537 (18)0.2313 (3)0.31249 (9)0.0304
C5−0.04849 (19)0.2113 (3)0.33919 (9)0.0311
C6−0.00659 (19)0.3116 (3)0.35112 (9)0.0321
C7−0.02107 (18)0.4323 (3)0.33784 (8)0.0309
C80.02424 (18)0.5405 (3)0.35143 (9)0.0317
C90.05738 (17)0.6155 (3)0.32052 (9)0.0290
C100.0464 (2)0.7449 (4)0.31806 (10)0.0384
C110.0760 (2)0.8175 (4)0.28992 (11)0.0431
C120.1154 (2)0.7594 (4)0.26308 (11)0.0408
C130.12687 (18)0.6316 (3)0.26431 (9)0.0304
C140.16828 (19)0.5669 (3)0.23429 (10)0.0342
C150.13041 (18)0.4641 (3)0.21166 (9)0.0291
C160.15761 (19)0.3438 (3)0.21164 (9)0.0329
C170.12149 (19)0.2453 (3)0.19366 (9)0.0329
C180.05767 (18)0.2655 (3)0.17417 (9)0.0315
C190.02885 (18)0.3857 (3)0.17266 (8)0.0289
C20−0.04104 (18)0.4070 (3)0.15165 (8)0.0321
C21−0.09681 (17)0.4562 (3)0.17646 (8)0.0274
C22−0.12971 (19)0.5685 (3)0.16751 (9)0.0331
C23−0.18030 (19)0.6160 (3)0.18957 (10)0.0345
C24−0.19669 (19)0.5492 (3)0.22246 (9)0.0324
C25−0.07966 (18)0.4501 (3)0.31274 (8)0.0286
C260.09994 (18)0.5601 (3)0.29420 (9)0.0270
C270.06721 (18)0.4841 (3)0.19084 (9)0.0298
C28−0.11674 (17)0.3890 (3)0.20906 (9)0.0269
C29−0.0336 (2)0.0874 (4)0.35388 (10)0.0401
N30−0.0225 (2)−0.0119 (3)0.36587 (10)0.0520
C310.1504 (2)0.1185 (4)0.19617 (10)0.0398
N320.17173 (19)0.0195 (4)0.19923 (11)0.0533
O33−0.09751 (12)0.5706 (2)0.30097 (6)0.0307
C34−0.1406 (2)0.6342 (4)0.32702 (10)0.0389
C35−0.1527 (2)0.7663 (4)0.31376 (11)0.0447
C36−0.1926 (3)0.8391 (4)0.34246 (13)0.0589
O370.11401 (12)0.4343 (2)0.29594 (6)0.0318
C380.1672 (2)0.3982 (4)0.32532 (10)0.0408
C390.1975 (2)0.2771 (4)0.31373 (12)0.0498
C400.1457 (3)0.1729 (4)0.30550 (13)0.0569
O410.03734 (12)0.6013 (2)0.18968 (6)0.0317
C420.0610 (2)0.6836 (3)0.15999 (10)0.0393
C430.0217 (2)0.8039 (3)0.16186 (10)0.0381
C440.0428 (2)0.8993 (4)0.13194 (10)0.0423
C490.17093 (19)0.5917 (3)0.43020 (9)0.0317
C500.10659 (19)0.6705 (3)0.43161 (9)0.0349
C510.10631 (18)0.7754 (3)0.46104 (9)0.0307
C520.08556 (18)0.8947 (4)0.44904 (10)0.0349
C530.08259 (18)0.9916 (3)0.47558 (10)0.0325
C540.09891 (19)0.9688 (3)0.51519 (10)0.0331
C550.12074 (18)0.8517 (3)0.52829 (9)0.0306
C560.13606 (19)0.8299 (4)0.57130 (9)0.0355
C570.20346 (18)0.7647 (3)0.58309 (8)0.0283
C580.20567 (19)0.6579 (3)0.60630 (9)0.0330
C590.2675 (2)0.5972 (3)0.61645 (9)0.0346
C600.32872 (19)0.6413 (3)0.60260 (9)0.0319
C610.32819 (17)0.7484 (3)0.57941 (8)0.0270
C620.39482 (17)0.7946 (3)0.56404 (9)0.0298
C630.39364 (17)0.8188 (3)0.52035 (9)0.0284
C640.41060 (18)0.9367 (3)0.50711 (9)0.0320
C650.41053 (18)0.9598 (3)0.46702 (9)0.0324
C660.39656 (18)0.8650 (4)0.44069 (9)0.0343
C670.37943 (17)0.7453 (3)0.45318 (9)0.0310
C680.3638 (2)0.6409 (4)0.42359 (10)0.0391
C690.2944 (2)0.5771 (3)0.42600 (9)0.0327
C700.2899 (2)0.4486 (4)0.42981 (10)0.0413
C710.2271 (2)0.3895 (4)0.43268 (10)0.0437
C720.1679 (2)0.4625 (3)0.43377 (9)0.0393
C730.12332 (17)0.7547 (3)0.50084 (9)0.0276
C740.26602 (17)0.8110 (3)0.57113 (8)0.0249
C750.37822 (18)0.7248 (3)0.49324 (9)0.0306
C760.23460 (19)0.6481 (3)0.42400 (8)0.0286
C770.0631 (2)1.1155 (4)0.46194 (11)0.0386
N780.04860 (18)1.2140 (3)0.45042 (10)0.0490
C790.4238 (2)1.0858 (4)0.45415 (10)0.0397
N800.43288 (19)1.1876 (4)0.44481 (10)0.0534
O810.14712 (12)0.6391 (2)0.51289 (6)0.0324
C820.0958 (2)0.5522 (3)0.52443 (11)0.0370
C830.1314 (2)0.4333 (4)0.53708 (11)0.0415
C840.0813 (2)0.3380 (4)0.55222 (12)0.0476
O850.26478 (12)0.9211 (2)0.54991 (6)0.0280
C860.2820 (3)1.0317 (4)0.57184 (12)0.0621
C870.2569 (3)1.1425 (4)0.55306 (12)0.0538
C880.2576 (2)1.1503 (4)0.50982 (12)0.0531
O890.35794 (12)0.6090 (2)0.50624 (6)0.0325
C900.4122 (2)0.5221 (4)0.51573 (11)0.0388
C910.3820 (2)0.4065 (4)0.53278 (12)0.0440
C920.4371 (2)0.3138 (4)0.54757 (14)0.0558
O100−0.08424 (14)0.2768 (2)0.21819 (7)0.0406
C101−0.1158 (5)0.1686 (8)0.2079 (2)0.03780.7000
C102−0.0723 (4)0.0606 (6)0.2238 (2)0.04660.7000
C103−0.1108 (4)−0.0648 (6)0.2199 (2)0.05610.7000
C201−0.1361 (12)0.166 (2)0.1935 (6)0.04590.3000
C202−0.0973 (7)0.0466 (11)0.1968 (4)0.03620.3000
C203−0.0836 (9)−0.0023 (15)0.2385 (5)0.05060.3000
O1100.23755 (13)0.7757 (2)0.41760 (6)0.0315
C1110.2177 (8)0.813 (2)0.3791 (6)0.03650.6000
C1120.2513 (6)0.9416 (12)0.3704 (3)0.05360.6000
C1130.2363 (9)1.0425 (14)0.4005 (3)0.06500.6000
C2110.2384 (13)0.805 (4)0.3753 (9)0.03730.4000
C2120.2127 (9)0.9321 (18)0.3702 (5)0.05550.4000
C2130.2559 (14)1.022 (2)0.3899 (5)0.07090.4000
H81−0.00360.59670.36500.0408*
H820.06020.50850.36880.0408*
H341−0.11870.63410.35260.0554*
H342−0.18390.59270.32720.0554*
H352−0.10920.80590.31190.0589*
H351−0.17730.76640.28890.0589*
H363−0.19960.92330.33400.0756*
H361−0.16790.83860.36730.0756*
H362−0.23600.79910.34430.0756*
H22−0.21460.42330.28230.0406*
H21−0.20330.29300.26350.0406*
H241−0.23010.58270.23850.0429*
H231−0.20310.69250.18250.0438*
H221−0.11760.61350.14510.0413*
H201−0.03520.46610.13140.0363*
H202−0.05650.32940.14060.0363*
H4210.10890.69990.16540.0511*
H4220.05380.64650.13490.0511*
H4320.02920.83880.18720.0490*
H431−0.02590.78530.15690.0490*
H4430.01640.97400.13370.0561*
H4420.09040.91830.13690.0561*
H4410.03520.86480.10650.0561*
H1420.20820.53120.24750.0458*
H1410.18190.62820.21630.0458*
H1210.13540.80830.24370.0501*
H1110.06920.90590.28920.0591*
H1010.01780.78390.33590.0467*
H1610.20190.32830.22430.0451*
H1810.03400.19710.16150.0396*
H41−0.13310.16210.30360.0401*
H610.03240.29730.36880.0413*
H3810.14730.38830.34960.0502*
H3820.20180.46140.32760.0502*
H3910.22940.25010.33430.0678*
H3920.22130.29130.29090.0678*
H4030.16890.09880.29820.0689*
H4020.12180.15680.32810.0689*
H4010.11370.19800.28480.0689*
H7210.12460.42380.43700.0534*
H7110.22450.30060.43410.0560*
H7010.33090.39970.43010.0533*
H6810.39910.57920.42730.0468*
H6820.36510.67630.39830.0468*
H9010.44450.55860.53450.0515*
H9020.43500.50120.49300.0515*
H9120.35490.43020.55350.0580*
H9110.35350.36650.51290.0580*
H9210.41610.24150.55790.0754*
H9220.46570.35330.56750.0754*
H9230.46430.28950.52690.0754*
H6410.42101.00280.52510.0421*
H6610.39850.88090.41360.0468*
H6220.40710.87090.57710.0367*
H6210.42930.73320.57030.0367*
H8620.26191.02480.59620.0896*
H8610.33081.03650.57610.0896*
H8710.28521.20930.56330.0684*
H8720.21081.15540.55980.0684*
H8820.24051.22960.50090.0667*
H8830.30341.13940.50220.0667*
H8810.22891.08550.49870.0667*
H5810.16350.62610.61480.0415*
H5910.26800.52560.63290.0437*
H6010.37100.59860.60890.0410*
H5620.13560.90920.58400.0431*
H5610.10000.77890.58000.0431*
H8220.07230.58600.54540.0484*
H8210.06360.53580.50300.0484*
H8320.16580.45220.55730.0553*
H8310.15260.39820.51550.0553*
H8420.10510.26330.56010.0616*
H8430.06010.37310.57380.0616*
H8410.04690.31900.53210.0616*
H5010.07030.61500.43720.0507*
H5020.09700.70620.40650.0507*
H5210.07290.91070.42230.0425*
H5410.09381.03480.53340.0421*
H1011−0.15930.16520.21900.0678*0.7000
H1012−0.12250.16040.18040.0678*0.7000
H1022−0.06130.07580.25080.0602*0.7000
H1021−0.03100.05850.21050.0602*0.7000
H1031−0.0833−0.13250.23010.0671*0.7000
H1033−0.1522−0.06040.23300.0671*0.7000
H1032−0.1219−0.07770.19280.0671*0.7000
H2011−0.18140.16400.20230.0699*0.3000
H2012−0.13830.19060.16680.0699*0.3000
H2022−0.1261−0.00830.18110.0589*0.3000
H2021−0.05290.05010.18680.0589*0.3000
H2033−0.0637−0.08350.23700.0599*0.3000
H2032−0.1274−0.00870.24910.0599*0.3000
H2031−0.05420.04980.25470.0599*0.3000
H11110.16880.82060.37550.0458*0.6000
H11120.23340.75420.36100.0458*0.6000
H11220.30000.93060.37240.0800*0.6000
H11210.23700.97140.34510.0800*0.6000
H11330.25901.11910.39530.0631*0.6000
H11320.25081.01460.42610.0631*0.6000
H11310.18771.05540.39880.0631*0.6000
H21120.28290.78860.36650.0458*0.4000
H21110.20550.75040.36240.0458*0.4000
H21210.16550.94200.37540.0897*0.4000
H21220.21820.94830.34350.0897*0.4000
H21320.23981.10360.38290.0699*0.4000
H21310.25061.00830.41690.0699*0.4000
H21330.30331.01460.38500.0699*0.4000
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0296 (18)0.031 (2)0.0216 (14)0.0004 (15)−0.0024 (12)−0.0020 (13)
C20.0264 (19)0.037 (2)0.0306 (16)−0.0001 (16)0.0047 (13)0.0016 (15)
C30.0315 (19)0.030 (2)0.0204 (14)0.0001 (15)0.0075 (13)0.0012 (13)
C40.034 (2)0.035 (2)0.0234 (15)0.0012 (16)0.0076 (13)−0.0026 (14)
C50.041 (2)0.029 (2)0.0242 (15)0.0053 (16)0.0093 (14)0.0000 (14)
C60.033 (2)0.041 (2)0.0230 (15)0.0141 (16)0.0059 (13)0.0029 (15)
C70.037 (2)0.039 (2)0.0172 (14)−0.0026 (16)0.0088 (13)−0.0047 (14)
C80.034 (2)0.038 (2)0.0237 (15)0.0014 (16)0.0048 (13)−0.0069 (14)
C90.0288 (19)0.0247 (19)0.0327 (17)−0.0021 (15)−0.0032 (13)−0.0081 (14)
C100.039 (2)0.036 (2)0.0401 (19)0.0013 (17)−0.0023 (16)−0.0119 (16)
C110.051 (3)0.025 (2)0.052 (2)−0.0012 (18)−0.0068 (19)−0.0071 (17)
C120.045 (2)0.036 (2)0.041 (2)−0.0083 (18)−0.0032 (17)0.0004 (17)
C130.034 (2)0.028 (2)0.0290 (16)−0.0029 (15)−0.0012 (14)−0.0029 (14)
C140.031 (2)0.037 (2)0.0351 (18)−0.0022 (16)0.0083 (14)0.0027 (15)
C150.0303 (19)0.036 (2)0.0216 (14)−0.0021 (15)0.0092 (13)0.0027 (13)
C160.031 (2)0.041 (2)0.0280 (16)0.0037 (16)0.0072 (14)0.0057 (15)
C170.037 (2)0.038 (2)0.0251 (16)0.0053 (17)0.0092 (14)0.0040 (15)
C180.038 (2)0.034 (2)0.0232 (15)0.0019 (16)0.0087 (14)−0.0037 (14)
C190.0335 (19)0.037 (2)0.0169 (14)0.0001 (16)0.0072 (13)0.0011 (13)
C200.039 (2)0.040 (2)0.0180 (14)0.0022 (16)0.0030 (13)0.0010 (14)
C210.0304 (19)0.031 (2)0.0201 (14)−0.0009 (15)−0.0011 (13)0.0016 (13)
C220.037 (2)0.037 (2)0.0242 (15)−0.0016 (16)−0.0014 (14)0.0038 (14)
C230.040 (2)0.028 (2)0.0344 (17)0.0117 (16)−0.0011 (15)0.0011 (15)
C240.038 (2)0.030 (2)0.0294 (16)0.0043 (16)0.0038 (14)−0.0026 (14)
C250.040 (2)0.030 (2)0.0173 (14)0.0038 (16)0.0109 (13)0.0021 (13)
C260.0305 (19)0.0220 (19)0.0281 (16)−0.0004 (14)−0.0011 (13)−0.0024 (13)
C270.036 (2)0.034 (2)0.0212 (15)0.0044 (16)0.0116 (14)0.0058 (13)
C280.0305 (19)0.0250 (19)0.0252 (15)0.0087 (15)0.0019 (13)0.0028 (13)
C290.051 (3)0.044 (3)0.0253 (16)0.0104 (19)0.0039 (15)−0.0024 (16)
N300.072 (3)0.041 (2)0.0420 (18)0.0242 (19)−0.0011 (17)−0.0006 (16)
C310.041 (2)0.046 (3)0.0321 (18)0.003 (2)0.0026 (15)0.0038 (16)
N320.049 (2)0.045 (2)0.065 (2)0.0191 (19)−0.0049 (17)0.0016 (18)
O330.0414 (15)0.0279 (13)0.0232 (10)0.0030 (11)0.0047 (10)0.0024 (9)
C340.044 (2)0.043 (2)0.0306 (17)0.0147 (18)0.0074 (15)0.0033 (16)
C350.056 (3)0.038 (2)0.0394 (19)0.0112 (19)−0.0041 (18)−0.0023 (17)
C360.066 (3)0.052 (3)0.057 (3)0.030 (2)−0.006 (2)−0.007 (2)
O370.0391 (15)0.0288 (14)0.0275 (11)0.0032 (11)0.0026 (10)0.0007 (9)
C380.044 (2)0.043 (2)0.0352 (18)0.0048 (18)−0.0037 (16)0.0031 (16)
C390.054 (3)0.051 (3)0.044 (2)0.013 (2)0.0024 (19)0.0054 (19)
C400.070 (3)0.045 (3)0.056 (2)0.014 (2)0.005 (2)0.006 (2)
O410.0383 (14)0.0306 (14)0.0276 (11)0.0004 (11)0.0118 (10)0.0037 (10)
C420.052 (2)0.037 (2)0.0300 (17)0.0028 (18)0.0151 (16)0.0094 (15)
C430.049 (2)0.030 (2)0.0355 (18)−0.0023 (17)0.0093 (16)0.0004 (15)
C440.060 (3)0.028 (2)0.0386 (19)−0.0007 (18)0.0012 (18)0.0003 (16)
C490.041 (2)0.030 (2)0.0222 (15)0.0008 (16)−0.0051 (14)−0.0034 (14)
C500.038 (2)0.039 (2)0.0269 (16)−0.0055 (17)−0.0033 (14)−0.0018 (15)
C510.0286 (19)0.033 (2)0.0297 (16)0.0015 (15)−0.0012 (13)−0.0006 (14)
C520.0254 (19)0.047 (2)0.0320 (17)−0.0038 (17)−0.0007 (14)−0.0012 (16)
C530.031 (2)0.032 (2)0.0342 (18)0.0021 (16)0.0016 (14)0.0015 (15)
C540.036 (2)0.033 (2)0.0303 (17)0.0088 (16)0.0031 (14)−0.0010 (15)
C550.0283 (19)0.037 (2)0.0278 (16)−0.0020 (16)0.0068 (13)−0.0034 (14)
C560.039 (2)0.041 (2)0.0279 (16)0.0060 (17)0.0082 (15)−0.0026 (15)
C570.034 (2)0.032 (2)0.0191 (14)−0.0037 (15)0.0070 (13)−0.0006 (13)
C580.038 (2)0.040 (2)0.0222 (15)−0.0029 (17)0.0081 (14)0.0013 (14)
C590.047 (2)0.030 (2)0.0265 (16)−0.0071 (17)0.0035 (15)0.0082 (14)
C600.037 (2)0.034 (2)0.0249 (15)−0.0007 (16)0.0022 (14)0.0054 (14)
C610.0341 (19)0.0292 (19)0.0180 (14)−0.0039 (15)0.0037 (12)−0.0012 (13)
C620.0295 (19)0.037 (2)0.0229 (15)−0.0089 (15)0.0027 (13)0.0015 (14)
C630.0231 (18)0.037 (2)0.0249 (15)−0.0024 (15)0.0002 (13)0.0026 (14)
C640.031 (2)0.036 (2)0.0293 (16)−0.0015 (16)0.0040 (14)0.0024 (15)
C650.0289 (19)0.037 (2)0.0321 (17)0.0031 (16)0.0067 (14)0.0099 (15)
C660.029 (2)0.049 (2)0.0255 (16)0.0022 (17)0.0062 (14)0.0069 (16)
C670.0268 (19)0.043 (2)0.0244 (15)0.0051 (16)0.0085 (13)0.0006 (15)
C680.041 (2)0.049 (2)0.0275 (16)0.0065 (19)0.0042 (15)−0.0047 (16)
C690.046 (2)0.028 (2)0.0242 (15)0.0038 (16)0.0013 (14)−0.0048 (14)
C700.055 (3)0.038 (2)0.0303 (17)0.015 (2)−0.0027 (16)−0.0054 (16)
C710.076 (3)0.023 (2)0.0314 (18)0.001 (2)−0.0038 (18)−0.0026 (15)
C720.062 (3)0.031 (2)0.0247 (16)−0.0077 (19)−0.0020 (16)−0.0042 (14)
C730.0228 (18)0.030 (2)0.0295 (16)0.0001 (14)0.0015 (13)0.0010 (14)
C740.0316 (19)0.0210 (18)0.0221 (14)0.0026 (14)0.0024 (12)0.0008 (13)
C750.0281 (19)0.034 (2)0.0297 (16)−0.0002 (16)0.0065 (13)0.0040 (15)
C760.045 (2)0.0214 (19)0.0188 (14)−0.0020 (16)0.0003 (13)−0.0021 (12)
C770.035 (2)0.036 (2)0.045 (2)0.0035 (18)0.0012 (16)0.0009 (18)
N780.048 (2)0.043 (2)0.055 (2)0.0035 (17)−0.0035 (16)0.0070 (17)
C790.037 (2)0.046 (3)0.0364 (18)−0.0025 (18)0.0058 (16)0.0117 (17)
N800.049 (2)0.059 (3)0.053 (2)0.0004 (18)0.0093 (17)0.0179 (18)
O810.0345 (14)0.0291 (14)0.0333 (12)0.0036 (11)−0.0001 (10)0.0006 (10)
C820.040 (2)0.031 (2)0.0408 (19)−0.0005 (17)0.0075 (16)0.0016 (16)
C830.048 (2)0.041 (2)0.0363 (18)0.0029 (19)0.0075 (17)−0.0004 (16)
C840.057 (3)0.042 (2)0.045 (2)0.007 (2)0.0086 (18)0.0043 (18)
O850.0384 (14)0.0204 (12)0.0249 (10)−0.0030 (10)0.0007 (9)0.0034 (9)
C860.111 (4)0.038 (3)0.036 (2)0.000 (3)−0.004 (2)0.0040 (18)
C870.073 (3)0.038 (3)0.050 (2)0.005 (2)0.003 (2)0.0028 (19)
C880.059 (3)0.047 (3)0.053 (2)0.000 (2)0.001 (2)0.016 (2)
O890.0347 (14)0.0311 (14)0.0322 (12)−0.0015 (11)0.0061 (10)0.0018 (10)
C900.040 (2)0.036 (2)0.041 (2)0.0012 (17)0.0042 (16)0.0030 (16)
C910.047 (2)0.039 (2)0.047 (2)0.0018 (19)0.0098 (18)0.0048 (18)
C920.060 (3)0.045 (3)0.061 (3)−0.002 (2)0.002 (2)0.013 (2)
O1000.0472 (16)0.0383 (16)0.0376 (13)0.0172 (13)0.0110 (11)0.0094 (11)
C1010.049 (6)0.025 (4)0.039 (5)−0.010 (4)0.004 (3)−0.005 (4)
C1020.059 (4)0.019 (4)0.065 (5)−0.001 (3)0.026 (4)−0.002 (3)
C1030.053 (4)0.039 (4)0.078 (5)−0.003 (3)0.018 (4)0.010 (4)
C2010.050 (12)0.039 (9)0.047 (12)−0.013 (8)−0.013 (8)−0.010 (9)
C2020.050 (8)0.029 (7)0.028 (6)0.009 (6)−0.006 (6)−0.012 (5)
C2030.075 (12)0.009 (8)0.067 (10)−0.015 (7)−0.002 (8)−0.002 (7)
O1100.0448 (15)0.0284 (14)0.0214 (10)0.0009 (11)0.0019 (10)0.0017 (9)
C1110.034 (9)0.054 (5)0.022 (5)−0.011 (8)0.008 (6)0.003 (4)
C1120.098 (9)0.031 (4)0.032 (3)0.005 (7)0.009 (6)0.003 (3)
C1130.133 (11)0.033 (6)0.031 (5)0.015 (6)0.023 (4)−0.004 (4)
C2110.030 (12)0.065 (7)0.019 (6)−0.004 (10)0.010 (8)0.012 (5)
C2120.100 (12)0.033 (6)0.033 (5)0.005 (10)0.005 (9)0.012 (4)
C2130.130 (13)0.037 (8)0.045 (10)0.018 (8)0.000 (8)0.003 (8)
Geometric parameters (Å, º) top
C1—C21.510 (4)C57—C741.398 (5)
C1—C241.370 (5)C58—C591.385 (5)
C1—C281.397 (5)C58—H5810.950
C2—C31.518 (5)C59—C601.391 (5)
C2—H220.950C59—H5910.950
C2—H210.950C60—C611.391 (5)
C3—C41.375 (5)C60—H6010.950
C3—C251.396 (5)C61—C621.512 (5)
C4—C51.402 (5)C61—C741.390 (5)
C4—H410.950C62—C631.523 (4)
C5—C61.387 (5)C62—H6220.950
C5—C291.435 (5)C62—H6210.950
C6—C71.386 (5)C63—C641.382 (5)
C6—H610.950C63—C751.386 (5)
C7—C81.504 (5)C64—C651.401 (4)
C7—C251.392 (5)C64—H6410.950
C8—C91.509 (5)C65—C661.371 (5)
C8—H810.950C65—C791.441 (6)
C8—H820.950C66—C671.392 (5)
C9—C101.396 (5)C66—H6610.950
C9—C261.398 (5)C67—C681.523 (5)
C10—C111.393 (6)C67—C751.397 (4)
C10—H1010.950C68—C691.517 (5)
C11—C121.384 (6)C68—H6810.950
C11—H1110.950C68—H6820.950
C12—C131.380 (5)C69—C701.378 (5)
C12—H1210.950C69—C761.382 (5)
C13—C141.517 (5)C70—C711.380 (6)
C13—C261.408 (5)C70—H7010.950
C14—C151.505 (5)C71—C721.390 (6)
C14—H1420.950C71—H7110.950
C14—H1410.950C72—H7210.950
C15—C161.385 (5)C73—O811.369 (4)
C15—C271.393 (5)C74—O851.380 (4)
C16—C171.383 (5)C75—O891.378 (4)
C16—H1610.950C76—O1101.379 (4)
C17—C181.383 (5)C77—N781.149 (5)
C17—C311.462 (6)C79—N801.148 (5)
C18—C191.397 (5)O81—C821.434 (4)
C18—H1810.950C82—C831.493 (5)
C19—C201.508 (5)C82—H8220.950
C19—C271.406 (5)C82—H8210.950
C20—C211.517 (5)C83—C841.522 (6)
C20—H2010.950C83—H8320.950
C20—H2020.950C83—H8310.950
C21—C221.380 (5)C84—H8420.950
C21—C281.407 (4)C84—H8430.950
C22—C231.378 (5)C84—H8410.950
C22—H2210.950O85—C861.426 (5)
C23—C241.391 (5)C86—C871.415 (6)
C23—H2310.950C86—H8620.950
C24—H2410.950C86—H8610.950
C25—O331.382 (4)C87—C881.491 (6)
C26—O371.368 (4)C87—H8710.950
C27—O411.375 (4)C87—H8720.950
C28—O1001.377 (4)C88—H8820.950
C29—N301.150 (5)C88—H8830.950
C31—N321.135 (5)C88—H8810.950
O33—C341.437 (4)O89—C901.423 (4)
C34—C351.492 (5)C90—C911.500 (5)
C34—H3410.950C90—H9010.950
C34—H3420.950C90—H9020.950
C35—C361.509 (6)C91—C921.516 (6)
C35—H3520.950C91—H9120.950
C35—H3510.950C91—H9110.950
C36—H3630.950C92—H9210.950
C36—H3610.950C92—H9220.950
C36—H3620.950C92—H9230.950
O37—C381.445 (4)O100—C1011.341 (8)
C38—C391.483 (6)O100—C2011.731 (19)
C38—H3810.950C101—C1021.506 (11)
C38—H3820.950C101—H10110.950
C39—C401.510 (6)C101—H10120.950
C39—H3910.950C102—C1031.531 (9)
C39—H3920.950C102—H10220.950
C40—H4030.950C102—H10210.950
C40—H4020.950C103—H10310.950
C40—H4010.950C103—H10330.950
O41—C421.445 (4)C103—H10320.950
C42—C431.494 (5)C201—C2021.48 (3)
C42—H4210.950C201—H20110.950
C42—H4220.950C201—H20120.950
C43—C441.522 (5)C202—C2031.53 (2)
C43—H4320.950C202—H20220.950
C43—H4310.950C202—H20210.950
C44—H4430.950C203—H20330.950
C44—H4420.950C203—H20320.950
C44—H4410.950C203—H20310.950
C49—C501.508 (5)O110—C1111.41 (2)
C49—C721.382 (5)O110—C2111.49 (3)
C49—C761.403 (5)C111—C1121.55 (3)
C50—C511.507 (5)C111—H11110.950
C50—H5010.950C111—H11120.950
C50—H5020.950C112—C1131.535 (15)
C51—C521.387 (5)C112—H11220.950
C51—C731.403 (4)C112—H11210.950
C52—C531.381 (5)C113—H11330.950
C52—H5210.950C113—H11320.950
C53—C541.398 (5)C113—H11310.950
C53—C771.442 (5)C211—C2121.45 (5)
C54—C551.383 (5)C211—H21120.950
C54—H5410.950C211—H21110.950
C55—C561.506 (4)C212—C2131.41 (3)
C55—C731.402 (5)C212—H21210.950
C56—C571.511 (5)C212—H21220.950
C56—H5620.950C213—H21320.950
C56—H5610.950C213—H21310.950
C57—C581.389 (5)C213—H21330.950
C2—C1—C24120.5 (3)C60—C59—H591120.1
C2—C1—C28121.4 (3)C59—C60—C61120.0 (3)
C24—C1—C28118.1 (3)C59—C60—H601120.2
C1—C2—C3114.9 (3)C61—C60—H601119.7
C1—C2—H22107.0C60—C61—C62119.6 (3)
C3—C2—H22107.5C60—C61—C74118.8 (3)
C1—C2—H21109.1C62—C61—C74121.5 (3)
C3—C2—H21108.8C61—C62—C63116.4 (3)
H22—C2—H21109.5C61—C62—H622107.8
C2—C3—C4120.4 (3)C63—C62—H622107.9
C2—C3—C25121.0 (3)C61—C62—H621107.6
C4—C3—C25118.6 (3)C63—C62—H621107.5
C3—C4—C5120.4 (3)H622—C62—H621109.5
C3—C4—H41119.9C62—C63—C64119.4 (3)
C5—C4—H41119.7C62—C63—C75121.9 (3)
C4—C5—C6119.7 (3)C64—C63—C75118.6 (3)
C4—C5—C29120.0 (3)C63—C64—C65120.0 (3)
C6—C5—C29120.3 (3)C63—C64—H641120.2
C5—C6—C7121.0 (3)C65—C64—H641119.8
C5—C6—H61119.4C64—C65—C66120.5 (3)
C7—C6—H61119.6C64—C65—C79118.6 (3)
C6—C7—C8120.5 (3)C66—C65—C79121.0 (3)
C6—C7—C25118.0 (3)C65—C66—C67120.7 (3)
C8—C7—C25121.5 (3)C65—C66—H661119.7
C7—C8—C9117.1 (3)C67—C66—H661119.5
C7—C8—H81107.3C66—C67—C68120.2 (3)
C9—C8—H81107.3C66—C67—C75117.9 (3)
C7—C8—H82107.9C68—C67—C75121.9 (3)
C9—C8—H82107.7C67—C68—C69115.3 (3)
H81—C8—H82109.5C67—C68—H681107.9
C8—C9—C10119.6 (3)C69—C68—H681108.4
C8—C9—C26122.2 (3)C67—C68—H682107.8
C10—C9—C26118.2 (3)C69—C68—H682107.8
C9—C10—C11121.4 (3)H681—C68—H682109.5
C9—C10—H101119.0C68—C69—C70120.8 (4)
C11—C10—H101119.5C68—C69—C76119.9 (3)
C10—C11—C12119.2 (4)C70—C69—C76119.3 (4)
C10—C11—H111120.3C69—C70—C71121.5 (4)
C12—C11—H111120.4C69—C70—H701119.1
C11—C12—C13121.1 (4)C71—C70—H701119.4
C11—C12—H121119.6C70—C71—C72118.8 (4)
C13—C12—H121119.3C70—C71—H711120.6
C12—C13—C14121.3 (3)C72—C71—H711120.7
C12—C13—C26119.2 (3)C71—C72—C49121.0 (4)
C14—C13—C26119.5 (3)C71—C72—H721120.0
C13—C14—C15114.8 (3)C49—C72—H721119.0
C13—C14—H142108.0C51—C73—C55121.6 (3)
C15—C14—H142108.0C51—C73—O81119.2 (3)
C13—C14—H141108.4C55—C73—O81119.0 (3)
C15—C14—H141108.1C57—C74—C61121.9 (3)
H142—C14—H141109.5C57—C74—O85118.1 (3)
C14—C15—C16120.1 (3)C61—C74—O85119.9 (3)
C14—C15—C27122.3 (3)C67—C75—C63122.2 (3)
C16—C15—C27117.6 (3)C67—C75—O89119.0 (3)
C15—C16—C17121.3 (3)C63—C75—O89118.8 (3)
C15—C16—H161119.6C49—C76—C69120.2 (3)
C17—C16—H161119.1C49—C76—O110119.5 (3)
C16—C17—C18120.5 (3)C69—C76—O110120.2 (3)
C16—C17—C31119.6 (3)C53—C77—N78178.4 (4)
C18—C17—C31119.9 (3)C65—C79—N80177.7 (4)
C17—C18—C19120.2 (3)C73—O81—C82116.0 (3)
C17—C18—H181119.4O81—C82—C83108.2 (3)
C19—C18—H181120.4O81—C82—H822110.2
C18—C19—C20120.0 (3)C83—C82—H822109.7
C18—C19—C27117.9 (3)O81—C82—H821109.7
C20—C19—C27122.1 (3)C83—C82—H821109.6
C19—C20—C21115.8 (3)H822—C82—H821109.5
C19—C20—H201107.5C82—C83—C84111.8 (3)
C21—C20—H201108.0C82—C83—H832108.7
C19—C20—H202108.0C84—C83—H832108.9
C21—C20—H202108.0C82—C83—H831108.9
H201—C20—H202109.5C84—C83—H831109.1
C20—C21—C22120.7 (3)H832—C83—H831109.5
C20—C21—C28121.2 (3)C83—C84—H842110.4
C22—C21—C28118.1 (3)C83—C84—H843109.1
C21—C22—C23122.1 (3)H842—C84—H843109.5
C21—C22—H221118.7C83—C84—H841108.9
C23—C22—H221119.2H842—C84—H841109.5
C22—C23—C24118.2 (3)H843—C84—H841109.5
C22—C23—H231120.7C74—O85—C86115.3 (2)
C24—C23—H231121.1O85—C86—C87112.8 (4)
C23—C24—C1122.4 (3)O85—C86—H862107.8
C23—C24—H241119.0C87—C86—H862108.5
C1—C24—H241118.6O85—C86—H861108.7
C3—C25—C7122.1 (3)C87—C86—H861109.5
C3—C25—O33118.8 (3)H862—C86—H861109.5
C7—C25—O33119.1 (3)C86—C87—C88118.4 (4)
C13—C26—C9120.7 (3)C86—C87—H871106.5
C13—C26—O37118.6 (3)C88—C87—H871106.3
C9—C26—O37120.7 (3)C86—C87—H872108.0
C19—C27—C15122.3 (3)C88—C87—H872107.9
C19—C27—O41117.0 (3)H871—C87—H872109.5
C15—C27—O41120.6 (3)C87—C88—H882110.0
C21—C28—C1121.1 (3)C87—C88—H883110.0
C21—C28—O100118.5 (3)H882—C88—H883109.5
C1—C28—O100120.4 (3)C87—C88—H881108.4
C5—C29—N30179.1 (4)H882—C88—H881109.5
C17—C31—N32177.7 (4)H883—C88—H881109.5
C25—O33—C34113.6 (2)C75—O89—C90115.7 (3)
O33—C34—C35109.9 (3)O89—C90—C91108.7 (3)
O33—C34—H341109.6O89—C90—H901109.3
C35—C34—H341109.6C91—C90—H901109.1
O33—C34—H342109.7O89—C90—H902110.0
C35—C34—H342108.6C91—C90—H902110.2
H341—C34—H342109.5H901—C90—H902109.5
C34—C35—C36111.2 (3)C90—C91—C92112.4 (3)
C34—C35—H352108.4C90—C91—H912109.1
C36—C35—H352108.2C92—C91—H912109.6
C34—C35—H351109.6C90—C91—H911108.2
C36—C35—H351109.9C92—C91—H911108.1
H352—C35—H351109.5H912—C91—H911109.5
C35—C36—H363110.7C91—C92—H921110.1
C35—C36—H361109.7C91—C92—H922108.4
H363—C36—H361109.5H921—C92—H922109.5
C35—C36—H362108.0C91—C92—H923109.9
H363—C36—H362109.5H921—C92—H923109.5
H361—C36—H362109.5H922—C92—H923109.5
C26—O37—C38114.9 (3)C28—O100—C101119.5 (4)
O37—C38—C39108.7 (3)C28—O100—C201103.7 (8)
O37—C38—H381109.3O100—C101—C102109.0 (6)
C39—C38—H381109.4O100—C101—H1011109.2
O37—C38—H382109.6C102—C101—H1011108.4
C39—C38—H382110.3O100—C101—H1012111.7
H381—C38—H382109.5C102—C101—H1012109.0
C38—C39—C40114.7 (4)H1011—C101—H1012109.5
C38—C39—H391108.2C101—C102—C103112.1 (6)
C40—C39—H391107.9C101—C102—H1022107.8
C38—C39—H392107.9C103—C102—H1022108.0
C40—C39—H392108.5C101—C102—H1021108.3
H391—C39—H392109.5C103—C102—H1021111.0
C39—C40—H403109.8H1022—C102—H1021109.5
C39—C40—H402109.7C102—C103—H1031111.8
H403—C40—H402109.5C102—C103—H1033109.8
C39—C40—H401109.0H1031—C103—H1033109.5
H403—C40—H401109.5C102—C103—H1032106.8
H402—C40—H401109.5H1031—C103—H1032109.5
C27—O41—C42114.7 (2)H1033—C103—H1032109.5
O41—C42—C43107.6 (3)O100—C201—C202105.8 (13)
O41—C42—H421109.1O100—C201—H2011112.4
C43—C42—H421109.3C202—C201—H2011115.4
O41—C42—H422110.8O100—C201—H2012106.0
C43—C42—H422110.6C202—C201—H2012107.2
H421—C42—H422109.5H2011—C201—H2012109.5
C42—C43—C44112.4 (3)C201—C202—C203114.7 (13)
C42—C43—H432109.2C201—C202—H2022102.2
C44—C43—H432109.2C203—C202—H2022112.2
C42—C43—H431107.8C201—C202—H2021114.0
C44—C43—H431108.6C203—C202—H2021104.5
H432—C43—H431109.5H2022—C202—H2021109.5
C43—C44—H443110.2C202—C203—H2033107.6
C43—C44—H442108.8C202—C203—H2032106.4
H443—C44—H442109.5H2033—C203—H2032109.5
C43—C44—H441109.4C202—C203—H2031114.3
H443—C44—H441109.5H2033—C203—H2031109.5
H442—C44—H441109.5H2032—C203—H2031109.5
C50—C49—C72120.7 (4)C76—O110—C111114.7 (10)
C50—C49—C76120.4 (3)C76—O110—C211111.5 (16)
C72—C49—C76118.9 (3)O110—C111—C112109.8 (15)
C49—C50—C51118.4 (3)O110—C111—H1111110.6
C49—C50—H501106.7C112—C111—H1111109.2
C51—C50—H501106.7O110—C111—H1112110.4
C49—C50—H502107.6C112—C111—H1112107.2
C51—C50—H502107.8H1111—C111—H1112109.5
H501—C50—H502109.5C111—C112—C113112.6 (11)
C50—C51—C52119.6 (3)C111—C112—H1122107.9
C50—C51—C73121.8 (3)C113—C112—H1122105.8
C52—C51—C73118.6 (3)C111—C112—H1121111.8
C51—C52—C53120.8 (3)C113—C112—H1121109.2
C51—C52—H521120.2H1122—C112—H1121109.5
C53—C52—H521119.0C112—C113—H1133111.1
C52—C53—C54119.8 (3)C112—C113—H1132110.3
C52—C53—C77119.4 (3)H1133—C113—H1132109.5
C54—C53—C77120.8 (3)C112—C113—H1131107.0
C53—C54—C55121.1 (3)H1133—C113—H1131109.5
C53—C54—H541119.1H1132—C113—H1131109.5
C55—C54—H541119.8O110—C211—C212107 (2)
C54—C55—C56119.6 (3)O110—C211—H2112110.1
C54—C55—C73118.0 (3)C212—C211—H2112116.6
C56—C55—C73122.3 (3)O110—C211—H2111105.8
C55—C56—C57116.3 (3)C212—C211—H2111107.7
C55—C56—H562107.9H2112—C211—H2111109.5
C57—C56—H562108.7C211—C212—C213113 (2)
C55—C56—H561107.4C211—C212—H2121114.2
C57—C56—H561107.1C213—C212—H2121112.5
H562—C56—H561109.5C211—C212—H2122103.0
C56—C57—C58121.5 (3)C213—C212—H2122103.9
C56—C57—C74120.8 (3)H2121—C212—H2122109.5
C58—C57—C74117.7 (3)C212—C213—H2132108.9
C57—C58—C59121.2 (3)C212—C213—H2131105.3
C57—C58—H581118.5H2132—C213—H2131109.5
C59—C58—H581120.3C212—C213—H2133114.0
C58—C59—C60120.1 (3)H2132—C213—H2133109.5
C58—C59—H591119.9H2131—C213—H2133109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H101···N30i0.952.553.392 (8)147
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC42H46N2O4
Mr642.84
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)19.398 (4), 10.6491 (12), 34.391 (2)
β (°) 93.987 (10)
V (Å3)7086.9 (16)
Z8
Radiation typeCu Kα
µ (mm−1)0.61
Crystal size (mm)0.40 × 0.33 × 0.12
Data collection
DiffractometerOxford Diffraction XCALIBUR
Absorption correctionAnalytical
(de Meulenaer & Tompa, 1965)
Tmin, Tmax0.83, 0.93
No. of measured, independent and
observed [I > 2σ(I)] reflections		44656, 14658, 7906
Rint0.103
(sin θ/λ)max (Å−1)0.634
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.083, 0.063, 1.10
No. of reflections7906
No. of parameters920
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.38, −0.41

Computer programs: CrysAlis CCD (Oxford Diffraction, 2002), CrysAlis RED (Oxford Diffraction, 2002), SIR92 (Altomare et al., 1994), CRYSTALS (Betteridge et al., 2003), CAMERON (Watkin et al., 1996).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H101···N30i0.952.553.392 (8)147
Symmetry code: (i) x, y+1, z.
 

Acknowledgements

We gratefully acknowledge financial support from the Ministry of Education, Youth and Sports of the Czech Republic (grant No. 6046137301).

References

First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals Google Scholar
 First citationBetteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationCasnati, A., Fochi, M., Minari, P., Pochini, A., Reggiani, M. & Ungaro, R. (1996). Gazz. Chim. Ital. 124, 99–106.  Google Scholar
 First citationMeulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014–1018.  CrossRef IUCr Journals Web of Science Google Scholar
 First citationGutsche, C. D. (2008). Calixarenes: An Introduction, 2nd ed., Monographs in Supramolecular Chemistry, edited by J. F. Stoddart, Cambridge: The Royal Society of Chemistry.  Google Scholar
 First citationOxford Diffraction (2002). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
 First citationPinkhassik, E., Sidorov, V. & Stibor, I. (1998). J. Org. Chem. 63, 9644–9651.  Web of Science CrossRef CAS Google Scholar
 First citationPinkhassik, E., Stibor, I., Casnati, A. & Ungaro, R. (1997). J. Org. Chem. 62, 8654–8659.  CrossRef CAS Web of Science Google Scholar
 First citationPrince, E. (1982). Mathematical Techniques in Crystallography and Materials Science. New York: Springer-Verlag.  Google Scholar
 First citationRao, C. P. & Dey, M. (2004). Calixarenes, Encyclopedia of Nanoscience and Nanotechnology, vol. 1, 475–497. Stevenson Ranch, California: American Scientific Publishers.  Google Scholar
 First citationSýkora, J., Budka, J., Lhoták, P., Stibor, I. & Císařová, I. (2005). Org. Biomol. Chem. 3, 2572–2578.  Web of Science PubMed Google Scholar
 First citationWatkin, D. (1994). Acta Cryst. A50, 411–437.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationWatkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.  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 66| Part 2| February 2010| Pages o419-o420
https://doi.org/10.1107/S1600536810002242
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