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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o419–o420.
Published online 2010 January 23. doi:  10.1107/S1600536810002242
PMCID: PMC2979721

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

Abstract

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 [triangle]); Rao & Dey (2004 [triangle]). For applications of the title compound, see: Pinkhassik et al. (1997 [triangle]; 1998 [triangle]). For details of the synthesis, see: Sýkora et al. (2005 [triangle]); Casnati et al. (1996 [triangle]). For the weighting scheme, see: Prince (1982 [triangle]); Watkin (1994 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o419-scheme1.jpg

Experimental

Crystal data

  • C42H46N2O4
  • M r = 642.84
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o419-efi1.jpg
  • 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 [triangle]) T min = 0.83, T max = 0.93
  • 44656 measured reflections
  • 14658 independent reflections
  • 7906 reflections with I > 2σ(I)
  • R int = 0.103

Refinement

  • R[F 2 > 2σ(F 2)] = 0.083
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002242/om2307Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

Fig. 1.
The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

Crystal data

C42H46N2O4F(000) = 2752
Mr = 642.84Dx = 1.205 Mg m3
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 mm1
β = 93.987 (10)°T = 150 K
V = 7086.9 (16) Å3Block, colorless
Z = 80.40 × 0.33 × 0.12 mm

Data collection

Oxford Diffraction XCALIBUR diffractometer14658 independent reflections
graphite7906 reflections with I > 2σ(I)
Detector resolution: 8.1917 pixels mm-1Rint = 0.103
[var phi] & 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

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 Å3
920 parametersΔρmin = −0.41 e Å3
18 restraints

Special details

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)

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)

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, °)

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, °)

D—H···AD—HH···AD···AD—H···A
C10—H101···N30i0.952.553.392 (8)147

Symmetry codes: (i) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: OM2307).

References

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