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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 2| February 2011| Pages o296-o297

5,11,17,23,29-Penta-tert-butyl-31,32,33,34,35-penta­propoxycalix[5]arene di­chloro­methane hemisolvate

aInstitute of Physics, AS CR, v.v.i, Na Slovance 2, 182 21 Prague 8, Czech Republic, bInstitute of Chemical Technology, Department of Organic Chemistry, Technická 5, 166 28 Prague 6, Czech Republic, cCharles University in Prague, Faculty of Science - Department of Inorganic Chemistry, Hlavova 2030/8, 128 43 Prague 2, Czech Republic, and dWest Bohemia University, Faculty of Applied Science, Univerzitní 22, 306 14 Plzeň, Czech Republic
*Correspondence e-mail: pojarova@fzu.cz

(Received 13 December 2010; accepted 5 January 2011; online 8 January 2011)

The title compound, tert-butyl­propoxycalix[5]arene, C70H100O5·0.5CH2Cl2, crystallizes as a solvate with two mol­ecules of calix[5]arene in 1,2-alternate conformations and one mol­ecule of dichloro­methane in the asymmetric unit. One tert-butyl group in one of the mol­ecules and two in the other are disordered over two positions with occupancy factors fixed at 0.5917:0.4083, 0.5901:0.4099 and 0.8535:0.1465, respectively, in the final refinement. The C atoms of a prop­oxy group in each of the mol­ecules are also disordered over two positions with occupancies of 0.7372:0.2628 and 0.5027:0.4973. The mol­ecules form intra­molecular hydrogen bonds between prop­oxy O atoms and an adjacent CH2 group in a neighbouring prop­oxy chain. In the crystal, inter­molecular C—H⋯O and C—H⋯Cl inter­actions occur involving the dichloro­methane mol­ecule.

Related literature

For the synthesis and NMR analysis of esters of p-tert-butyl­calix[5]arene, see: Stewart et al. (1995[Stewart, D. R., Krawiec, M., Kashyap, R. P., Watson, W. H. & Gutsche, C. D. (1995). J. Am. Chem. Soc. 117, 586-601.]). For the weighting scheme used, see: Watkin (1994[Watkin, D. (1994). Acta Cryst. A50, 411-437.]); Prince (1982[Prince, E. (1982). Mathematical Techniques in Crystallography and Materials Science. New York: Springer-Verlag.]).

[Scheme 1]

Experimental

Crystal data
  • C70H100O5·0.5CH2Cl2

  • Mr = 1064.03

  • Monoclinic, P 21 /c

  • a = 12.3740 (2) Å

  • b = 23.9130 (2) Å

  • c = 43.6550 (5) Å

  • β = 91.7460 (5)°

  • V = 12911.5 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 150 K

  • 0.45 × 0.23 × 0.12 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 39073 measured reflections

  • 20282 independent reflections

  • 13395 reflections with I > 2σ(I)

  • Rint = 0.043

  • θmax = 24.1°

Refinement
  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 0.151

  • S = 1.02

  • 20282 reflections

  • 1531 parameters

  • 220 restraints

  • H-atom parameters constrained

  • Δρmax = 1.88 e Å−3

  • Δρmin = −1.75 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C71—H711⋯O7 1.03 2.36 3.363 (8) 163
C48—H482⋯O1 0.99 2.60 3.351 (5) 134
C110—H1101⋯O8 1.00 2.57 3.361 (5) 136
C120—H1202⋯O9 1.00 2.57 3.371 (5) 136
C14—H142⋯O3 1.01 2.47 2.869 (5) 103
C38—H382⋯Cl1 0.97 2.92 3.795 (5) 151

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); 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: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: CRYSTALS and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The studied compound was prepared by alkylation of tert-butylcalix[5]arene with propyl iodide in a presence of NaH and crystallized from mixture of dichloromethane and methanol. Molecules of dichloromethane are present in the crystal structure. The asymmetric unit contains two molecules of calix[5]arene which are turned to each other in direction of the b axis at an angle of 67/% (angle between planes formed by the bridging CH2 groups). This leads to the formation of infinite channels along the a axis by half of the molecules. The channels are separated by layers of turned molecules. The solvent molecule forms C—H···O hydrogen bonds. Hydrogen atom (H711) of the CH2 group in dichloromethane point toward O7, the distance between HC—H···O is 2.36 Å, and the chlorine atom has close contact to the terminal CH3 group of the propoxy chain (the HC—H···Cl distance is 2.92 Å). In each macrocycle two propoxy chains point above the cavity, while the others are turned out. The orientation toward the cavity is caused by intra-molecular hydrogen bonds between a methylene group of a propoxy chain and a neighbouring oxygen atom (C110-H1101···O8, C120-H1202···O9, C48—H482···O1, the distances are given in Table 1). Two disordered positions were modeled for three tert-butyl groups and the C atoms of two propoxy groups. The disorder components were found from difference electron density maps and their occupancy factors were fixed after several cycles of refinement as follows: tert-butyl groups with central carbon atoms: C67 - 0.59:0.40; C137 - 0.59:0.41; C138 - 0.85:0.15; propoxy group bound to oxygen atoms: O1 - 0.7372:0.2628 and O6 - 0.5027: 0.4973.

Related literature top

For the synthesis and NMR analysis of esters of p-tert-butylcalix[5]arene, see: Stewart et al. (1995). For the weighting scheme used, see: Watkin (1994); Prince (1982).

Experimental top

To the solution of 250 mg (0.3 mmol) of 1 in 15 ml of dry DMF cooled to 0 °C was added 123 mg (3 mmol) of 60% suspension of NaH in mineral oil and the mixture was stirred for 15 minutes. Then, 0.45 ml of propyl iodide was added and the reaction was stirred at room temperature. After two days, the mixture was poured into 30 ml of 1 M HCl and extracted 3 τimes 20 ml of dichloromethane. Combined extracts were washed with 20 ml of water and 20 ml of brine and dried over MgSO4. The drying agent was filtered off and the filtrate was evaporated to dryness. The crude product was dissolved in 10 ml of dichloromethane, 10 ml of MeOH was added and the mixture was slowly evaporated in an open flask. After two days, 235 mg (75%) of the white crystals of product 2 was obtained.

NMR spectra corresponded with data in the literature (Stewart et al., 1995) - on a compound prepared using a different procedure, in acetonitrile with K2CO3, yield 83%. MS-ESI+: C70H100O5 required 1020.76; found 1043.71 ([M+Na]+; 100%), 1059.70 ([M+K]+; 10%)

Refinement top

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 > 2sigma(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. The position of disordered atoms were located from difference maps of electron density. Disordered fragments were then placed in appropriate positions, and all distances between neighbouring atoms and angles were restrained. Site occupancies were refined for the different parts with the same thermal parameters for the same atoms in the various fragments. At the end of refinement, site occupancies were fixed and hydrogen atoms were placed in calculated positions with the thermal parameters Uiso(H) (in the range 1.2–1.5 times Ueq of the parent atom).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: CRYSTALS (Betteridge et al., 2003) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. A view of first molecule of 1 with atom's numbering. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are drawn as dashed lines. Hydrogen atoms not participating in hydrogen bonds are omitted. For clarity only the major disorder component of the disordered tert-butyl and propoxy groups are shown.
[Figure 2] Fig. 2. A view of second molecule of 1 with atom's numbering. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are drawn as dashed lines. Hydrogen atoms not participating in hydrogen bonds are omitted. For clarity only the major disorder component of the disordered tert-butyl and propoxy groups are shown.
[Figure 3] Fig. 3. The asymmetric unit of 1.
5,11,17,23,29-Penta-tert-butyl-31,32,33,34,35-pentapropoxycalix[5]arene dichloromethane hemisolvate top
Crystal data top
C70H100O5·0.5CH2Cl2F(000) = 4648
Mr = 1064.03Dx = 1.095 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 390743 reflections
a = 12.3740 (2) Åθ = 1.0–24.1°
b = 23.9130 (2) ŵ = 0.11 mm1
c = 43.6550 (5) ÅT = 150 K
β = 91.7460 (5)°Plate, colourless
V = 12911.5 (3) Å30.45 × 0.23 × 0.12 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer
Rint = 0.043
Graphite monochromatorθmax = 24.1°, θmin = 1.3°
ω/2θ scansh = 1414
39073 measured reflectionsk = 2727
20282 independent reflectionsl = 5050
13395 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.151 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: 11.5 14.0 3.91
S = 1.02(Δ/σ)max = 0.001
20282 reflectionsΔρmax = 1.88 e Å3
1531 parametersΔρmin = 1.75 e Å3
220 restraints
Crystal data top
C70H100O5·0.5CH2Cl2V = 12911.5 (3) Å3
Mr = 1064.03Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.3740 (2) ŵ = 0.11 mm1
b = 23.9130 (2) ÅT = 150 K
c = 43.6550 (5) Å0.45 × 0.23 × 0.12 mm
β = 91.7460 (5)°
Data collection top
Nonius KappaCCD
diffractometer
13395 reflections with I > 2σ(I)
39073 measured reflectionsRint = 0.043
20282 independent reflectionsθmax = 24.1°
Refinement top
R[F2 > 2σ(F2)] = 0.074220 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.02Δρmax = 1.88 e Å3
20282 reflectionsΔρmin = 1.75 e Å3
1531 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.57648 (17)0.44344 (8)0.53618 (5)0.1149
Cl20.75149 (18)0.42717 (11)0.49435 (7)0.1499
O10.3168 (2)0.36142 (11)0.61877 (6)0.0385
O20.4804 (2)0.27551 (11)0.70453 (6)0.0369
O30.2037 (2)0.23598 (12)0.73657 (7)0.0465
O40.0814 (2)0.19447 (12)0.69175 (7)0.0446
O50.0087 (2)0.31590 (12)0.62105 (6)0.0396
O70.4990 (2)0.38058 (11)0.44291 (6)0.0350
O80.44330 (19)0.26652 (11)0.50838 (6)0.0313
O90.21648 (19)0.13254 (11)0.46283 (6)0.0317
O100.2735 (2)0.18753 (12)0.38854 (6)0.0394
C10.0976 (3)0.23706 (17)0.59817 (9)0.0331
C20.1905 (3)0.27406 (17)0.58846 (9)0.0354
C30.2992 (3)0.26365 (17)0.60504 (9)0.0327
C40.3457 (3)0.21050 (17)0.60532 (9)0.0344
C50.4462 (3)0.19915 (17)0.61923 (9)0.0343
C60.4981 (3)0.24336 (17)0.63415 (9)0.0336
C70.4556 (3)0.29704 (16)0.63505 (9)0.0324
C80.5175 (3)0.34373 (17)0.65123 (9)0.0369
C90.4690 (3)0.36604 (16)0.68048 (9)0.0321
C100.4440 (3)0.42264 (17)0.68304 (9)0.0366
C110.3998 (3)0.44602 (17)0.70921 (9)0.0366
C120.3743 (3)0.40857 (17)0.73253 (9)0.0367
C130.3977 (3)0.35146 (17)0.73122 (9)0.0331
C140.3679 (3)0.31298 (18)0.75739 (9)0.0368
C150.2511 (3)0.31707 (17)0.76683 (9)0.0349
C160.2218 (3)0.35663 (19)0.78843 (9)0.0410
C170.1162 (3)0.36135 (19)0.79821 (9)0.0421
C180.0403 (3)0.32465 (19)0.78536 (9)0.0422
C190.0651 (3)0.28482 (18)0.76340 (10)0.0379
C200.0241 (3)0.24950 (19)0.74867 (10)0.0442
C210.0819 (3)0.27921 (17)0.72163 (10)0.0368
C220.1100 (3)0.33538 (17)0.72356 (10)0.0390
C230.1610 (3)0.36469 (18)0.69960 (9)0.0363
C240.1785 (3)0.33557 (17)0.67210 (9)0.0355
C250.1519 (3)0.27880 (18)0.66909 (10)0.0376
C260.1724 (3)0.2503 (2)0.63880 (10)0.0442
C270.0753 (3)0.22581 (18)0.62280 (9)0.0366
C280.0759 (3)0.17028 (18)0.61437 (9)0.0382
C290.0059 (3)0.14613 (18)0.59739 (9)0.0382
C300.0907 (3)0.18102 (17)0.58940 (9)0.0355
C310.3570 (3)0.30688 (16)0.61932 (9)0.0313
C320.4498 (3)0.33161 (16)0.70573 (9)0.0331
C330.1723 (3)0.28035 (17)0.75489 (9)0.0356
C340.1069 (3)0.25127 (17)0.69434 (10)0.0373
C350.0118 (3)0.25910 (17)0.61450 (9)0.0345
C390.5932 (3)0.2661 (2)0.71254 (11)0.0482
C400.6153 (4)0.2544 (2)0.74556 (11)0.0555
C410.5689 (5)0.1992 (2)0.75635 (14)0.0754
C420.2004 (4)0.2471 (2)0.70448 (10)0.0486
C430.2555 (6)0.2000 (3)0.68780 (14)0.0846
C440.2068 (7)0.1459 (3)0.6895 (2)0.1284
C450.1665 (4)0.1582 (2)0.70146 (14)0.0657
C460.1239 (5)0.0991 (2)0.70335 (16)0.0791
C470.0469 (6)0.0912 (3)0.73034 (18)0.1052
C480.0753 (3)0.33122 (17)0.64732 (10)0.0390
C490.0738 (4)0.39336 (19)0.65105 (11)0.0499
C500.1414 (4)0.4096 (3)0.67903 (15)0.0842
C510.5002 (3)0.14147 (18)0.61738 (11)0.0440
C520.4236 (4)0.09687 (19)0.60426 (13)0.0609
C530.5965 (4)0.1456 (2)0.59599 (13)0.0665
C540.5408 (5)0.1230 (2)0.64941 (12)0.0711
C550.3829 (4)0.50901 (18)0.71227 (11)0.0441
C560.4919 (5)0.5358 (2)0.7190 (2)0.1149
C570.3044 (5)0.5239 (2)0.73684 (14)0.0875
C580.3378 (6)0.5344 (2)0.68244 (13)0.0828
C590.0816 (4)0.4055 (2)0.82133 (10)0.0552
C600.1754 (5)0.4432 (3)0.83163 (14)0.0818
C610.0371 (6)0.3769 (3)0.84946 (12)0.0914
C620.0046 (4)0.4437 (2)0.80613 (12)0.0727
C630.1956 (3)0.42560 (18)0.70422 (10)0.0396
C640.0977 (4)0.46152 (19)0.71482 (12)0.0556
C650.2798 (4)0.4267 (2)0.72898 (11)0.0547
C660.2449 (4)0.45182 (19)0.67507 (10)0.0477
C710.6226 (5)0.4543 (3)0.49944 (17)0.0921
C720.4129 (3)0.18398 (17)0.35096 (9)0.0337
C730.3859 (3)0.24204 (16)0.33889 (9)0.0360
C740.4649 (3)0.28711 (16)0.35017 (9)0.0331
C750.5754 (3)0.27735 (18)0.35251 (9)0.0368
C760.6493 (3)0.31754 (18)0.36326 (9)0.0366
C770.6063 (3)0.36744 (18)0.37403 (9)0.0386
C780.4954 (3)0.37921 (16)0.37216 (9)0.0325
C790.4527 (3)0.43374 (17)0.38472 (10)0.0401
C800.3719 (3)0.43022 (16)0.41026 (9)0.0329
C810.2732 (3)0.45755 (16)0.40702 (10)0.0377
C820.1998 (3)0.46128 (16)0.43037 (9)0.0350
C830.2274 (3)0.43444 (16)0.45753 (10)0.0353
C840.3232 (3)0.40413 (16)0.46212 (9)0.0305
C850.3493 (3)0.37538 (16)0.49267 (9)0.0335
C860.2831 (3)0.32317 (16)0.49943 (8)0.0287
C870.1695 (3)0.32567 (16)0.49931 (9)0.0318
C880.1048 (3)0.27963 (16)0.50487 (9)0.0308
C890.1560 (3)0.22889 (16)0.51008 (8)0.0308
C900.2691 (3)0.22374 (16)0.51103 (8)0.0285
C910.3210 (3)0.16770 (16)0.51910 (9)0.0314
C920.3798 (3)0.13757 (15)0.49404 (9)0.0292
C930.4877 (3)0.12282 (16)0.49839 (9)0.0328
C940.5442 (3)0.09268 (16)0.47680 (10)0.0342
C950.4904 (3)0.08084 (16)0.44912 (10)0.0350
C960.3819 (3)0.09491 (16)0.44346 (9)0.0335
C970.3278 (3)0.08105 (17)0.41269 (9)0.0375
C980.3863 (3)0.10652 (17)0.38593 (9)0.0352
C990.4666 (3)0.07706 (18)0.37127 (9)0.0394
C1000.5235 (3)0.09963 (18)0.34715 (9)0.0386
C1010.4935 (3)0.15263 (17)0.33717 (9)0.0364
C1020.4273 (3)0.33965 (17)0.35875 (9)0.0338
C1030.3960 (3)0.40346 (16)0.43806 (9)0.0314
C1040.3314 (3)0.27171 (16)0.50648 (8)0.0300
C1050.3270 (3)0.12129 (15)0.46665 (9)0.0295
C1060.3597 (3)0.16010 (17)0.37535 (9)0.0340
C1100.5036 (3)0.32053 (16)0.43991 (9)0.0331
C1110.6159 (3)0.30165 (18)0.44939 (10)0.0429
C1120.6232 (4)0.2383 (2)0.44767 (13)0.0632
C1130.4892 (3)0.28464 (18)0.53762 (9)0.0356
C1140.6099 (3)0.2761 (2)0.53786 (10)0.0507
C1150.6632 (3)0.2964 (2)0.56753 (10)0.0601
C1160.1508 (3)0.08509 (18)0.46990 (10)0.0382
C1170.0337 (3)0.1005 (2)0.46478 (10)0.0458
C1180.0045 (4)0.1146 (2)0.43170 (12)0.0660
C1190.3045 (3)0.23067 (17)0.41036 (9)0.0374
C1200.2040 (3)0.25435 (18)0.42402 (10)0.0411
C1210.1302 (4)0.2835 (2)0.40130 (11)0.0589
C1220.7708 (3)0.30570 (19)0.36255 (11)0.0442
C1230.8015 (4)0.2962 (2)0.32900 (12)0.0616
C1240.8383 (4)0.3538 (2)0.37563 (13)0.0609
C1250.7994 (4)0.2530 (2)0.38076 (12)0.0546
C1260.0947 (3)0.49451 (18)0.42547 (11)0.0438
C1270.1222 (4)0.55546 (18)0.41810 (11)0.0509
C1280.0246 (4)0.4942 (2)0.45379 (12)0.0617
C1290.0298 (4)0.4691 (2)0.39812 (13)0.0670
C1300.0185 (3)0.28697 (17)0.50565 (10)0.0370
C1310.0611 (3)0.3027 (2)0.47376 (11)0.0600
C1320.0454 (3)0.33372 (19)0.52823 (11)0.0509
C1330.0763 (3)0.23437 (19)0.51616 (12)0.0532
C1340.6598 (3)0.07164 (18)0.48388 (12)0.0484
C1350.6575 (6)0.0370 (3)0.51548 (18)0.04760.5901
C1360.7090 (7)0.0358 (4)0.4610 (2)0.05960.5901
C1370.7350 (6)0.1218 (3)0.4924 (2)0.05170.5901
C3350.6565 (11)0.0080 (5)0.4800 (4)0.09550.4099
C3360.7242 (10)0.0847 (8)0.4528 (3)0.09750.4099
C3370.7146 (12)0.0991 (9)0.5083 (4)0.11250.4099
O60.3176 (2)0.35209 (12)0.35529 (7)0.0415
C1070.2872 (16)0.3702 (12)0.3248 (4)0.12490.5027
C1080.1665 (15)0.3862 (7)0.3215 (5)0.13790.5027
C1090.1217 (16)0.3326 (7)0.3150 (4)0.14660.5027
C2070.2826 (8)0.3635 (7)0.3245 (3)0.04070.4973
C2080.1594 (8)0.3581 (5)0.3250 (3)0.05860.4973
C2090.1099 (9)0.3696 (4)0.2938 (2)0.06360.4973
C1380.6146 (8)0.0672 (3)0.33234 (19)0.05770.8535
C1390.5640 (7)0.0173 (3)0.3152 (2)0.10070.8535
C1400.6942 (6)0.0454 (4)0.35689 (16)0.08830.8535
C1410.6763 (7)0.1023 (4)0.30980 (17)0.08760.8535
C3380.609 (3)0.0655 (14)0.3296 (8)0.04600.1465
C3390.559 (2)0.0436 (12)0.2993 (5)0.03990.1465
C3400.648 (3)0.0148 (12)0.3481 (6)0.04220.1465
C3410.703 (3)0.1045 (14)0.3230 (7)0.04390.1465
C670.0038 (8)0.0843 (7)0.5877 (3)0.03500.5917
C680.0996 (8)0.0536 (5)0.5973 (2)0.05290.5917
C690.0100 (8)0.0801 (4)0.5524 (2)0.05610.5917
C700.1009 (8)0.0532 (5)0.6022 (3)0.06570.5917
C2670.0053 (17)0.0842 (12)0.5897 (5)0.06500.4083
C2680.1104 (14)0.0634 (8)0.5840 (4)0.08050.4083
C2690.0613 (15)0.0728 (7)0.5598 (4)0.08500.4083
C2700.0613 (16)0.0525 (7)0.6163 (4)0.08470.4083
C360.3429 (9)0.3941 (3)0.59245 (19)0.04230.7372
C370.2926 (7)0.4505 (3)0.59579 (18)0.05390.7372
C380.3076 (6)0.4872 (3)0.56818 (15)0.06000.7372
C2360.326 (3)0.3806 (10)0.5872 (5)0.04320.2628
C2370.2568 (16)0.4308 (7)0.5791 (4)0.05140.2628
C2380.281 (2)0.4777 (8)0.6015 (5)0.06200.2628
H210.17010.31480.59160.0471*
H220.20130.26850.56590.0474*
H410.30620.17960.59590.0466*
H610.56840.23700.64440.0453*
H810.59220.32970.65670.0501*
H820.52330.37600.63660.0500*
H1010.45790.44740.66560.0494*
H1210.33730.42270.75080.0494*
H1410.41590.32270.77560.0502*
H1420.38390.27330.75110.0504*
H1610.27770.38240.79680.0556*
H1810.03460.32640.79220.0551*
H2020.07930.24060.76430.0595*
H2010.00740.21300.74140.0594*
H2210.09430.35540.74300.0529*
H2410.20990.35560.65400.0495*
H2610.22290.21800.64230.0594*
H2620.20870.27770.62490.0592*
H2810.13730.14660.62050.0522*
H3010.14820.16540.57740.0465*
H3920.63740.30030.70630.0611*
H3910.61670.23280.70040.0615*
H4010.58270.28600.75770.0734*
H4020.69670.25400.74980.0733*
H4130.58740.19260.77820.1181*
H4120.49010.19840.75300.1179*
H4110.60040.16820.74400.1183*
H4220.23950.28510.70130.0648*
H4210.12330.25160.69660.0644*
H4310.33350.19540.69640.1075*
H4320.25900.20930.66470.1077*
H4410.24560.11870.67680.1933*
H4430.21540.13390.71200.1936*
H4420.13080.14890.68360.1932*
H4510.19490.17020.72210.0873*
H4520.22890.16030.68590.0874*
H4620.18530.07160.70500.1030*
H4610.08470.09050.68400.1034*
H4710.02600.05170.73240.1573*
H4730.08330.10350.74960.1573*
H4720.01890.11440.72790.1570*
H4810.04610.31290.66640.0532*
H4820.15090.31820.64520.0526*
H4920.00280.40680.65310.0669*
H4910.10450.41090.63230.0677*
H5010.13800.45030.68230.1272*
H5020.11220.39090.69760.1272*
H5030.21690.39760.67650.1273*
H5220.45950.06030.60400.0990*
H5210.35980.09450.61720.0991*
H5230.39980.10670.58290.0991*
H5320.63190.10930.59420.1030*
H5310.65030.17250.60430.1032*
H5330.57160.15840.57560.1034*
H5430.57740.08640.64820.1111*
H5420.59400.15100.65800.1112*
H5410.47950.12020.66310.1110*
H5630.48350.57660.72060.1702*
H5620.51960.52110.73890.1702*
H5610.54160.52620.70300.1702*
H5710.28980.56400.73700.1418*
H5720.33540.51340.75710.1422*
H5730.23570.50370.73400.1421*
H5820.32740.57450.68510.1289*
H5810.26770.51580.67660.1296*
H5830.38890.52770.66580.1293*
H6020.14770.47140.84640.1233*
H6010.23440.42170.84190.1230*
H6030.20550.46390.81380.1233*
H6130.01850.40510.86460.1412*
H6120.08880.35040.85800.1410*
H6110.03020.35610.84300.1411*
H6230.02450.47330.82020.1209*
H6220.06930.42150.80000.1210*
H6210.02310.46160.78740.1215*
H6410.12370.49950.72030.0921*
H6420.06180.44470.73300.0920*
H6430.04550.46490.69780.0924*
H6520.30160.46620.73270.0903*
H6510.24880.41110.74850.0904*
H6530.34370.40530.72250.0900*
H6620.26430.49130.67900.0779*
H6610.31080.43130.66830.0779*
H6630.19200.45080.65870.0783*
H7120.62260.49540.49440.1125*
H7110.57060.43570.48360.1122*
H7310.31180.25240.34520.0471*
H7320.38490.24060.31590.0472*
H7510.60300.24080.34640.0485*
H7710.65400.39540.38270.0513*
H7910.51520.45680.39200.0545*
H7920.41550.45410.36690.0544*
H8110.25620.47520.38750.0513*
H8310.17900.43740.47440.0475*
H8510.33710.40300.50960.0452*
H8520.42940.36530.49340.0450*
H8710.13450.36150.49520.0425*
H8910.11270.19580.51300.0424*
H9110.37530.17350.53670.0441*
H9120.26430.14230.52660.0440*
H9310.52470.13490.51740.0446*
H9510.52890.06160.43310.0476*
H9720.25150.09520.41220.0492*
H9710.32570.03940.40990.0493*
H9910.48430.03890.37870.0513*
H10110.53130.16940.31980.0504*
H11010.44840.30330.45320.0450*
H11020.48550.30970.41770.0449*
H11120.63110.31520.47100.0582*
H11110.66960.31950.43560.0582*
H11230.69620.22520.45410.1011*
H11220.57180.22090.46160.1010*
H11210.60630.22420.42690.1009*
H11310.45530.26360.55480.0497*
H11320.47420.32600.54060.0493*
H11420.62570.23470.53530.0667*
H11410.63970.29650.51990.0662*
H11530.73910.28860.56800.0958*
H11520.63000.27840.58540.0962*
H11510.65230.33770.56910.0963*
H11610.16610.07270.49250.0508*
H11620.16950.05350.45590.0503*
H11710.01770.13390.47770.0607*
H11720.01470.06900.47180.0605*
H11820.07240.12480.42940.1040*
H11810.04880.14590.42490.1040*
H11830.01910.08210.41880.1044*
H11920.35390.21440.42720.0504*
H11910.34510.26090.39940.0500*
H12010.22610.28240.44080.0557*
H12020.16470.22320.43420.0554*
H12120.06700.29910.41130.0952*
H12110.16950.31450.39160.0950*
H12130.10710.25720.38530.0952*
H12320.87880.28790.32800.0989*
H12310.78520.33030.31690.0992*
H12330.75850.26490.31980.0994*
H12410.91450.34530.37370.1020*
H12430.82130.36000.39700.1019*
H12420.82140.38860.36370.1020*
H12510.87560.24420.37870.0908*
H12530.78610.25990.40250.0910*
H12520.75510.22090.37340.0911*
H12710.05580.57830.41600.0832*
H12720.16840.57120.43500.0832*
H12730.16290.55800.39900.0831*
H12820.04230.51550.44970.0959*
H12810.06510.51070.47160.0961*
H12830.00390.45550.45880.0962*
H12920.03750.48980.39480.1129*
H12910.01210.43030.40280.1131*
H12930.07190.47030.37930.1133*
H13110.13950.30840.47330.0978*
H13130.02720.33800.46710.0982*
H13120.04390.27270.45920.0981*
H13210.12420.33750.53050.0829*
H13230.01250.32580.54890.0832*
H13220.01800.36940.52080.0829*
H13310.15360.24050.51710.0869*
H13320.04870.22210.53670.0872*
H13330.06350.20350.50150.0870*
H13520.72760.02260.52090.0789*0.5901
H13510.63550.06040.53140.0789*0.5901
H13530.60850.00620.51330.0791*0.5901
H13620.77920.02160.46840.0938*0.5901
H13610.66120.00510.45550.0939*0.5901
H13630.72210.05820.44220.0941*0.5901
H13710.80320.10850.50170.0882*0.5901
H13730.69950.14790.50610.0883*0.5901
H13720.75180.14140.47340.0878*0.5901
H33510.72910.00600.47690.1489*0.4099
H33530.63000.00810.49880.1491*0.4099
H33520.61050.00190.46320.1489*0.4099
H33610.79410.06790.45320.1479*0.4099
H33620.72970.12380.44930.1479*0.4099
H33630.68220.06840.43490.1480*0.4099
H33720.79340.10660.50210.1601*0.4099
H33710.70970.08700.52690.1601*0.4099
H33730.68590.14190.50720.1602*0.4099
H10720.33610.40390.31960.1390*0.5027
H10710.30790.34110.30920.1392*0.5027
H10810.14310.40390.34050.1502*0.5027
H10820.15550.41130.30410.1502*0.5027
H10930.04680.33750.31150.1931*0.5027
H10920.13520.30820.33330.1932*0.5027
H10910.15600.31450.29770.1932*0.5027
H20720.30370.40000.31790.0561*0.4973
H20710.30840.33440.30990.0562*0.4973
H20810.12530.38570.33960.0739*0.4973
H20820.13860.32090.33240.0744*0.4973
H20930.03200.37270.29510.1000*0.4973
H20920.13850.40370.28590.0999*0.4973
H20910.12800.33990.28030.1000*0.4973
H13930.62230.00480.30630.1501*0.8535
H13920.52530.00630.32950.1498*0.8535
H13910.51460.03080.29870.1501*0.8535
H14010.75410.02580.34740.1381*0.8535
H14020.72400.07780.36870.1380*0.8535
H14030.65830.01990.37060.1380*0.8535
H14120.73620.08170.30170.1350*0.8535
H14110.70550.13610.32050.1354*0.8535
H14130.62800.11430.29260.1350*0.8535
H33920.62700.02600.28620.0670*0.1465
H33910.49870.01080.30580.0670*0.1465
H33930.51930.07990.28720.0670*0.1465
H34030.71930.00390.33970.0620*0.1465
H34020.66700.02910.36890.0620*0.1465
H34010.60200.01310.34810.0619*0.1465
H34130.74920.08830.30770.0640*0.1465
H34120.74240.11420.34060.0640*0.1465
H34110.67380.14000.31320.0641*0.1465
H6810.10120.01600.58860.0809*0.5917
H6820.10300.05140.61900.0809*0.5917
H6830.16460.07450.58920.0815*0.5917
H6920.01250.04130.54650.0860*0.5917
H6910.07570.09950.54520.0864*0.5917
H6930.05270.09780.54310.0858*0.5917
H7020.09100.01270.59940.0950*0.5917
H7010.10620.06070.62440.0955*0.5917
H7030.16510.06440.59310.0948*0.5917
H26830.11540.02770.57630.1291*0.4083
H26820.15200.06670.60370.1292*0.4083
H26810.14880.09070.56950.1291*0.4083
H26930.04040.03860.55120.1300*0.4083
H26920.13880.07350.56470.1299*0.4083
H26910.04470.10430.54550.1302*0.4083
H27010.05890.01340.61390.1320*0.4083
H27020.02030.06160.63570.1320*0.4083
H27030.13420.06640.61960.1321*0.4083
H3620.42240.39810.59090.0560*0.7372
H3610.31570.37590.57300.0564*0.7372
H3720.32360.46920.61480.0743*0.7372
H3710.21380.44600.59910.0742*0.7372
H3810.28060.52530.57140.0941*0.7372
H3820.38340.48940.56340.0939*0.7372
H3830.26790.47180.55020.0941*0.7372
H23620.40070.38600.58220.0560*0.2628
H23610.29750.34880.57340.0561*0.2628
H23720.18310.42170.58170.0740*0.2628
H23710.27240.44280.55920.0740*0.2628
H23810.24070.51110.59560.0960*0.2628
H23820.26710.46860.62220.0959*0.2628
H23830.35950.48850.60060.0961*0.2628
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1092 (15)0.0894 (13)0.1436 (19)0.0272 (11)0.0370 (13)0.0077 (13)
Cl20.0935 (15)0.1327 (19)0.221 (3)0.0327 (14)0.0447 (16)0.0620 (19)
O10.0387 (16)0.0324 (16)0.0447 (17)0.0002 (13)0.0078 (13)0.0051 (13)
O20.0309 (15)0.0334 (16)0.0466 (17)0.0001 (12)0.0045 (13)0.0025 (13)
O30.0501 (18)0.0413 (18)0.0481 (18)0.0043 (15)0.0009 (15)0.0003 (15)
O40.0384 (16)0.0338 (16)0.062 (2)0.0005 (13)0.0082 (14)0.0016 (14)
O50.0390 (16)0.0392 (17)0.0405 (16)0.0045 (13)0.0007 (13)0.0036 (13)
O70.0274 (14)0.0287 (15)0.0490 (17)0.0011 (12)0.0044 (12)0.0006 (13)
O80.0205 (13)0.0413 (16)0.0322 (14)0.0012 (11)0.0003 (11)0.0006 (12)
O90.0224 (13)0.0329 (15)0.0396 (16)0.0037 (11)0.0011 (11)0.0002 (12)
O100.0292 (15)0.0412 (17)0.0479 (17)0.0023 (13)0.0032 (13)0.0113 (14)
C10.030 (2)0.041 (2)0.028 (2)0.0029 (18)0.0029 (16)0.0001 (18)
C20.036 (2)0.037 (2)0.033 (2)0.0038 (18)0.0005 (18)0.0018 (18)
C30.030 (2)0.036 (2)0.032 (2)0.0023 (18)0.0068 (17)0.0053 (18)
C40.033 (2)0.035 (2)0.035 (2)0.0040 (18)0.0012 (17)0.0018 (18)
C50.033 (2)0.032 (2)0.038 (2)0.0001 (18)0.0041 (18)0.0030 (18)
C60.025 (2)0.043 (2)0.033 (2)0.0012 (18)0.0042 (17)0.0017 (18)
C70.031 (2)0.035 (2)0.031 (2)0.0034 (18)0.0099 (17)0.0005 (17)
C80.032 (2)0.037 (2)0.043 (2)0.0042 (18)0.0081 (18)0.0001 (19)
C90.028 (2)0.033 (2)0.035 (2)0.0044 (17)0.0032 (17)0.0000 (18)
C100.034 (2)0.038 (2)0.039 (2)0.0049 (18)0.0049 (18)0.0045 (19)
C110.035 (2)0.036 (2)0.039 (2)0.0004 (18)0.0013 (18)0.0018 (19)
C120.034 (2)0.040 (2)0.037 (2)0.0018 (19)0.0048 (18)0.0012 (19)
C130.026 (2)0.035 (2)0.038 (2)0.0036 (17)0.0012 (17)0.0027 (18)
C140.033 (2)0.046 (3)0.032 (2)0.0020 (19)0.0019 (17)0.0035 (19)
C150.035 (2)0.039 (2)0.031 (2)0.0003 (19)0.0007 (17)0.0081 (18)
C160.040 (2)0.044 (3)0.039 (2)0.003 (2)0.0010 (19)0.003 (2)
C170.041 (2)0.054 (3)0.031 (2)0.011 (2)0.0028 (19)0.004 (2)
C180.036 (2)0.055 (3)0.036 (2)0.006 (2)0.0056 (19)0.007 (2)
C190.033 (2)0.038 (2)0.042 (2)0.0002 (19)0.0030 (19)0.009 (2)
C200.042 (3)0.044 (3)0.047 (3)0.001 (2)0.001 (2)0.012 (2)
C210.027 (2)0.037 (2)0.046 (3)0.0027 (18)0.0021 (18)0.001 (2)
C220.036 (2)0.036 (2)0.044 (3)0.0050 (19)0.0028 (19)0.003 (2)
C230.032 (2)0.041 (2)0.036 (2)0.0050 (18)0.0014 (18)0.0014 (19)
C240.024 (2)0.043 (2)0.039 (2)0.0006 (18)0.0011 (17)0.0037 (19)
C250.025 (2)0.044 (3)0.044 (2)0.0025 (18)0.0043 (18)0.003 (2)
C260.032 (2)0.052 (3)0.049 (3)0.003 (2)0.003 (2)0.007 (2)
C270.026 (2)0.046 (3)0.038 (2)0.0047 (19)0.0004 (17)0.002 (2)
C280.029 (2)0.044 (3)0.042 (2)0.0006 (19)0.0000 (18)0.002 (2)
C290.034 (2)0.043 (2)0.037 (2)0.0002 (19)0.0024 (18)0.002 (2)
C300.027 (2)0.042 (2)0.037 (2)0.0035 (18)0.0019 (17)0.0028 (19)
C310.032 (2)0.031 (2)0.031 (2)0.0010 (17)0.0087 (17)0.0021 (17)
C320.027 (2)0.032 (2)0.040 (2)0.0016 (17)0.0012 (17)0.0008 (18)
C330.039 (2)0.036 (2)0.032 (2)0.0056 (19)0.0045 (18)0.0074 (18)
C340.024 (2)0.032 (2)0.056 (3)0.0026 (17)0.0074 (19)0.002 (2)
C350.033 (2)0.036 (2)0.033 (2)0.0063 (18)0.0060 (17)0.0020 (18)
C390.033 (2)0.047 (3)0.064 (3)0.005 (2)0.002 (2)0.003 (2)
C400.042 (3)0.065 (3)0.060 (3)0.005 (2)0.002 (2)0.004 (3)
C410.072 (4)0.070 (4)0.085 (4)0.015 (3)0.009 (3)0.032 (3)
C420.049 (3)0.052 (3)0.045 (3)0.001 (2)0.004 (2)0.000 (2)
C430.107 (5)0.076 (4)0.071 (4)0.003 (4)0.022 (4)0.024 (3)
C440.130 (7)0.089 (6)0.169 (8)0.014 (5)0.048 (6)0.058 (6)
C450.050 (3)0.042 (3)0.106 (5)0.009 (2)0.006 (3)0.000 (3)
C460.089 (5)0.045 (3)0.104 (5)0.006 (3)0.015 (4)0.002 (3)
C470.104 (6)0.053 (4)0.158 (7)0.007 (4)0.004 (5)0.024 (4)
C480.031 (2)0.042 (3)0.044 (2)0.0002 (19)0.0057 (19)0.003 (2)
C490.037 (2)0.045 (3)0.069 (3)0.006 (2)0.007 (2)0.008 (2)
C500.044 (3)0.082 (4)0.127 (6)0.001 (3)0.005 (3)0.049 (4)
C510.040 (2)0.038 (2)0.053 (3)0.007 (2)0.007 (2)0.005 (2)
C520.056 (3)0.033 (3)0.093 (4)0.003 (2)0.013 (3)0.005 (3)
C530.047 (3)0.050 (3)0.104 (5)0.010 (2)0.017 (3)0.018 (3)
C540.087 (4)0.050 (3)0.075 (4)0.018 (3)0.022 (3)0.004 (3)
C550.045 (3)0.034 (2)0.054 (3)0.000 (2)0.009 (2)0.002 (2)
C560.074 (4)0.043 (4)0.227 (9)0.003 (3)0.004 (5)0.035 (5)
C570.126 (6)0.047 (3)0.093 (5)0.027 (3)0.055 (4)0.005 (3)
C580.137 (6)0.039 (3)0.073 (4)0.016 (3)0.020 (4)0.014 (3)
C590.055 (3)0.075 (4)0.035 (3)0.022 (3)0.005 (2)0.009 (2)
C600.076 (4)0.088 (4)0.080 (4)0.034 (3)0.026 (3)0.045 (4)
C610.123 (6)0.112 (5)0.040 (3)0.041 (5)0.023 (3)0.002 (3)
C620.070 (4)0.084 (4)0.063 (4)0.039 (3)0.004 (3)0.013 (3)
C630.042 (2)0.038 (2)0.038 (2)0.002 (2)0.0002 (19)0.0030 (19)
C640.059 (3)0.037 (3)0.070 (3)0.001 (2)0.009 (3)0.001 (2)
C650.058 (3)0.052 (3)0.055 (3)0.012 (2)0.012 (2)0.000 (2)
C660.055 (3)0.042 (3)0.046 (3)0.006 (2)0.002 (2)0.006 (2)
C710.065 (4)0.067 (4)0.144 (7)0.001 (3)0.014 (4)0.006 (4)
C720.032 (2)0.036 (2)0.034 (2)0.0034 (18)0.0007 (17)0.0058 (18)
C730.034 (2)0.035 (2)0.038 (2)0.0033 (18)0.0012 (18)0.0015 (19)
C740.035 (2)0.033 (2)0.031 (2)0.0009 (18)0.0052 (17)0.0052 (18)
C750.034 (2)0.038 (2)0.039 (2)0.0061 (19)0.0022 (18)0.0002 (19)
C760.030 (2)0.042 (2)0.038 (2)0.0001 (19)0.0016 (18)0.0031 (19)
C770.039 (2)0.038 (2)0.039 (2)0.0038 (19)0.0042 (19)0.0030 (19)
C780.038 (2)0.032 (2)0.028 (2)0.0006 (18)0.0038 (17)0.0029 (17)
C790.046 (3)0.030 (2)0.045 (3)0.0020 (19)0.011 (2)0.0043 (19)
C800.037 (2)0.027 (2)0.034 (2)0.0016 (18)0.0049 (18)0.0012 (17)
C810.041 (2)0.029 (2)0.043 (2)0.0024 (19)0.0002 (19)0.0014 (19)
C820.034 (2)0.028 (2)0.043 (2)0.0016 (17)0.0018 (19)0.0005 (18)
C830.032 (2)0.029 (2)0.045 (2)0.0021 (18)0.0045 (18)0.0027 (19)
C840.029 (2)0.028 (2)0.034 (2)0.0016 (17)0.0022 (17)0.0001 (17)
C850.029 (2)0.032 (2)0.040 (2)0.0011 (17)0.0003 (17)0.0047 (18)
C860.028 (2)0.030 (2)0.028 (2)0.0014 (16)0.0008 (16)0.0031 (16)
C870.028 (2)0.032 (2)0.036 (2)0.0042 (17)0.0019 (17)0.0036 (18)
C880.025 (2)0.036 (2)0.031 (2)0.0031 (17)0.0042 (16)0.0058 (17)
C890.026 (2)0.034 (2)0.033 (2)0.0015 (17)0.0030 (16)0.0034 (18)
C900.0247 (19)0.033 (2)0.028 (2)0.0019 (16)0.0007 (15)0.0045 (17)
C910.028 (2)0.033 (2)0.034 (2)0.0016 (17)0.0038 (17)0.0025 (17)
C920.026 (2)0.027 (2)0.035 (2)0.0015 (16)0.0042 (16)0.0043 (17)
C930.031 (2)0.032 (2)0.034 (2)0.0012 (17)0.0001 (17)0.0037 (18)
C940.023 (2)0.031 (2)0.049 (3)0.0007 (17)0.0051 (18)0.0054 (19)
C950.030 (2)0.030 (2)0.046 (3)0.0012 (17)0.0121 (19)0.0007 (19)
C960.031 (2)0.030 (2)0.039 (2)0.0020 (17)0.0026 (18)0.0029 (18)
C970.036 (2)0.037 (2)0.040 (2)0.0034 (19)0.0060 (19)0.0026 (19)
C980.037 (2)0.034 (2)0.035 (2)0.0007 (18)0.0035 (18)0.0034 (18)
C990.045 (3)0.036 (2)0.038 (2)0.007 (2)0.010 (2)0.0018 (19)
C1000.038 (2)0.041 (2)0.037 (2)0.0096 (19)0.0062 (19)0.0026 (19)
C1010.040 (2)0.039 (2)0.031 (2)0.0028 (19)0.0043 (18)0.0022 (18)
C1020.030 (2)0.035 (2)0.037 (2)0.0044 (18)0.0063 (17)0.0063 (18)
C1030.028 (2)0.025 (2)0.041 (2)0.0015 (16)0.0029 (17)0.0020 (18)
C1040.0235 (19)0.037 (2)0.030 (2)0.0004 (17)0.0044 (16)0.0028 (17)
C1050.0235 (19)0.027 (2)0.038 (2)0.0030 (16)0.0074 (17)0.0069 (17)
C1060.025 (2)0.037 (2)0.040 (2)0.0011 (17)0.0017 (17)0.0086 (19)
C1100.034 (2)0.031 (2)0.035 (2)0.0038 (17)0.0062 (17)0.0032 (18)
C1110.040 (2)0.044 (3)0.046 (3)0.007 (2)0.006 (2)0.008 (2)
C1120.055 (3)0.047 (3)0.089 (4)0.020 (2)0.023 (3)0.022 (3)
C1130.026 (2)0.048 (3)0.033 (2)0.0027 (18)0.0020 (17)0.0011 (19)
C1140.029 (2)0.089 (4)0.033 (2)0.004 (2)0.0002 (18)0.004 (2)
C1150.032 (2)0.107 (5)0.041 (3)0.012 (3)0.005 (2)0.006 (3)
C1160.029 (2)0.041 (2)0.044 (3)0.0063 (18)0.0038 (18)0.001 (2)
C1170.029 (2)0.060 (3)0.048 (3)0.005 (2)0.003 (2)0.009 (2)
C1180.047 (3)0.078 (4)0.072 (4)0.006 (3)0.013 (3)0.008 (3)
C1190.037 (2)0.034 (2)0.041 (2)0.0024 (18)0.0041 (19)0.0083 (19)
C1200.040 (2)0.038 (2)0.045 (3)0.008 (2)0.007 (2)0.001 (2)
C1210.046 (3)0.070 (4)0.062 (3)0.022 (3)0.011 (2)0.013 (3)
C1220.031 (2)0.048 (3)0.054 (3)0.002 (2)0.005 (2)0.002 (2)
C1230.038 (3)0.078 (4)0.069 (3)0.006 (3)0.012 (2)0.002 (3)
C1240.032 (3)0.059 (3)0.091 (4)0.002 (2)0.005 (3)0.007 (3)
C1250.040 (3)0.055 (3)0.069 (3)0.007 (2)0.001 (2)0.004 (3)
C1260.036 (2)0.041 (3)0.054 (3)0.008 (2)0.003 (2)0.000 (2)
C1270.060 (3)0.039 (3)0.054 (3)0.016 (2)0.001 (2)0.002 (2)
C1280.044 (3)0.065 (3)0.077 (4)0.023 (3)0.012 (3)0.013 (3)
C1290.049 (3)0.057 (3)0.093 (4)0.011 (3)0.023 (3)0.018 (3)
C1300.023 (2)0.038 (2)0.049 (3)0.0046 (18)0.0018 (18)0.002 (2)
C1310.029 (2)0.088 (4)0.062 (3)0.009 (3)0.005 (2)0.002 (3)
C1320.033 (2)0.048 (3)0.073 (3)0.004 (2)0.015 (2)0.013 (2)
C1330.025 (2)0.046 (3)0.090 (4)0.000 (2)0.011 (2)0.005 (3)
C1340.024 (2)0.040 (3)0.082 (4)0.0045 (19)0.005 (2)0.004 (2)
C1350.028 (4)0.046 (4)0.069 (5)0.012 (3)0.005 (3)0.023 (4)
C1360.036 (4)0.068 (5)0.074 (5)0.022 (4)0.007 (4)0.005 (4)
C1370.025 (4)0.046 (4)0.084 (6)0.005 (3)0.005 (4)0.013 (4)
C3350.040 (7)0.106 (10)0.140 (11)0.024 (7)0.005 (7)0.024 (9)
C3360.030 (6)0.132 (10)0.131 (10)0.030 (7)0.002 (6)0.012 (9)
C3370.044 (7)0.160 (13)0.132 (12)0.038 (8)0.018 (8)0.006 (11)
O60.0312 (15)0.0400 (17)0.0535 (19)0.0062 (13)0.0019 (13)0.0040 (14)
C1070.158 (15)0.108 (12)0.104 (11)0.000 (11)0.074 (10)0.035 (10)
C1080.182 (13)0.114 (11)0.112 (9)0.012 (10)0.085 (9)0.024 (9)
C1090.187 (14)0.132 (12)0.116 (10)0.014 (11)0.079 (10)0.012 (10)
C2070.021 (5)0.040 (6)0.060 (7)0.016 (4)0.003 (5)0.006 (5)
C2080.043 (5)0.058 (6)0.073 (6)0.010 (5)0.031 (4)0.007 (5)
C2090.068 (6)0.054 (6)0.067 (6)0.006 (5)0.033 (5)0.006 (5)
C1380.066 (4)0.054 (3)0.054 (4)0.023 (3)0.025 (3)0.003 (3)
C1390.109 (5)0.089 (5)0.106 (5)0.033 (4)0.031 (4)0.025 (4)
C1400.079 (4)0.110 (5)0.078 (4)0.057 (4)0.038 (4)0.033 (4)
C1410.086 (5)0.109 (6)0.071 (5)0.053 (5)0.050 (4)0.035 (5)
C3380.058 (8)0.047 (8)0.034 (8)0.024 (8)0.016 (7)0.001 (7)
C3390.054 (9)0.045 (9)0.020 (8)0.028 (8)0.010 (8)0.006 (8)
C3400.053 (11)0.045 (10)0.030 (10)0.029 (9)0.005 (9)0.005 (9)
C3410.051 (13)0.044 (12)0.038 (12)0.026 (11)0.007 (11)0.001 (11)
C670.024 (5)0.040 (7)0.041 (6)0.004 (5)0.008 (4)0.004 (5)
C680.052 (5)0.048 (5)0.060 (5)0.014 (4)0.013 (4)0.001 (4)
C690.067 (5)0.046 (5)0.055 (5)0.008 (4)0.004 (4)0.016 (4)
C700.065 (6)0.052 (5)0.079 (7)0.012 (5)0.017 (5)0.013 (5)
C2670.082 (13)0.040 (10)0.073 (11)0.002 (10)0.006 (10)0.029 (9)
C2680.098 (10)0.051 (8)0.092 (10)0.002 (7)0.004 (8)0.030 (7)
C2690.116 (10)0.044 (7)0.096 (9)0.003 (7)0.016 (8)0.025 (6)
C2700.122 (12)0.037 (7)0.094 (10)0.006 (8)0.007 (9)0.014 (8)
C360.041 (5)0.035 (5)0.052 (4)0.012 (4)0.009 (3)0.012 (3)
C370.078 (5)0.034 (4)0.051 (5)0.004 (4)0.013 (4)0.005 (4)
C380.079 (5)0.044 (4)0.058 (4)0.001 (3)0.005 (4)0.008 (3)
C2360.033 (9)0.031 (9)0.067 (9)0.011 (9)0.013 (8)0.015 (8)
C2370.072 (9)0.037 (8)0.046 (9)0.002 (7)0.017 (8)0.006 (7)
C2380.072 (9)0.042 (9)0.072 (9)0.005 (8)0.001 (8)0.004 (8)
Geometric parameters (Å, º) top
Cl1—C711.738 (7)C89—C901.404 (5)
Cl2—C711.742 (6)C89—H8910.967
O1—C311.396 (5)C90—C911.523 (5)
O1—C361.435 (8)C90—C1041.400 (5)
O1—C311.396 (5)C91—C921.514 (5)
O1—C2361.459 (18)C91—H9111.015
O2—C321.395 (5)C91—H9120.992
O2—C391.446 (5)C92—C931.389 (5)
O3—C331.391 (5)C92—C1051.400 (5)
O3—C421.426 (5)C93—C941.391 (5)
O4—C341.400 (5)C93—H9310.978
O4—C451.439 (5)C94—C951.391 (6)
O5—C351.389 (5)C94—C1341.539 (5)
O5—C481.439 (5)C95—C961.398 (5)
O7—C1031.398 (4)C95—H9510.974
O7—C1101.443 (4)C96—C971.519 (5)
O8—C1041.391 (4)C96—C1051.388 (5)
O8—C1131.448 (4)C97—C981.521 (5)
O9—C1051.399 (4)C97—H9721.003
O9—C1161.435 (5)C97—H9711.004
O10—C1061.392 (4)C98—C991.390 (5)
O10—C1191.448 (5)C98—C1061.398 (6)
C1—C21.520 (5)C99—C1001.393 (6)
C1—C301.396 (6)C99—H9910.991
C1—C351.400 (5)C100—C1011.387 (6)
C2—C31.529 (5)C100—C1381.529 (11)
C2—H211.016C100—C1011.387 (6)
C2—H221.007C100—C3381.56 (5)
C3—C41.395 (5)C101—H10110.987
C3—C311.393 (5)C102—O61.393 (4)
C4—C51.394 (5)C110—C1111.506 (5)
C4—H410.970C110—H11010.999
C5—C61.389 (5)C110—H11021.024
C5—C511.536 (6)C111—C1121.519 (6)
C6—C71.388 (5)C111—H11121.010
C6—H610.977C111—H11111.005
C7—C81.516 (5)C112—H11230.989
C7—C311.402 (5)C112—H11220.984
C8—C91.524 (5)C112—H11210.984
C8—H811.005C113—C1141.506 (5)
C8—H821.007C113—H11311.007
C9—C101.394 (6)C113—H11321.015
C9—C321.402 (5)C114—C1151.515 (6)
C10—C111.398 (6)C114—H11421.016
C10—H1010.984C114—H11411.002
C11—C121.399 (6)C115—H11530.956
C11—C551.527 (6)C115—H11520.992
C12—C131.398 (6)C115—H11511.000
C12—H1210.990C116—C1171.505 (5)
C13—C141.521 (5)C116—H11611.041
C13—C321.387 (5)C116—H11621.002
C14—C151.518 (5)C117—C1181.516 (6)
C14—H1411.006C117—H11711.001
C14—H1421.009C117—H11721.017
C15—C161.392 (6)C118—H11820.985
C15—C331.401 (6)C118—H11810.980
C16—C171.392 (6)C118—H11830.979
C16—H1610.988C119—C1201.506 (5)
C17—C181.391 (6)C119—H11921.018
C17—C591.531 (6)C119—H11911.008
C18—C191.392 (6)C120—C1211.500 (6)
C18—H1810.983C120—H12011.023
C19—C201.517 (6)C120—H12021.002
C19—C331.392 (5)C121—H12120.981
C20—C211.536 (6)C121—H12110.988
C20—H2021.003C121—H12130.976
C20—H2011.012C122—C1231.541 (6)
C21—C221.391 (6)C122—C1241.522 (6)
C21—C341.393 (6)C122—C1251.525 (6)
C22—C231.395 (6)C123—H12320.979
C22—H2210.987C123—H12310.990
C23—C241.399 (6)C123—H12330.997
C23—C631.533 (6)C124—H12410.970
C24—C251.404 (6)C124—H12430.975
C24—H2410.993C124—H12421.001
C25—C261.503 (6)C125—H12510.973
C25—C341.386 (6)C125—H12530.982
C26—C271.525 (5)C125—H12520.991
C26—H2611.007C126—C1271.533 (6)
C26—H2620.991C126—C1281.532 (6)
C27—C281.378 (6)C126—C1291.544 (6)
C27—C351.397 (6)C127—H12710.988
C28—C291.398 (6)C127—H12720.995
C28—H2810.990C127—H12730.988
C29—C301.393 (6)C128—H12820.985
C29—C2671.52 (3)C128—H12810.995
C29—C301.393 (6)C128—H12830.986
C29—C671.537 (18)C129—H12920.976
C30—H3010.971C129—H12910.977
C39—C401.485 (6)C129—H12930.987
C39—H3921.025C130—C1311.521 (6)
C39—H3911.006C130—C1321.533 (6)
C40—C411.521 (7)C130—C1331.525 (6)
C40—H4011.014C131—H13110.980
C40—H4021.018C131—H13130.991
C41—H4130.985C131—H13120.986
C41—H4120.982C132—H13210.987
C41—H4111.002C132—H13230.999
C42—C431.515 (7)C132—H13220.976
C42—H4221.040C133—H13310.970
C42—H4211.009C133—H13320.994
C43—C441.430 (9)C133—H13330.993
C43—H4311.031C134—C1351.611 (8)
C43—H4321.036C134—C1361.464 (8)
C44—H4410.987C134—C1371.555 (8)
C44—H4431.029C134—C3351.531 (12)
C44—H4420.969C134—C3361.626 (12)
C45—C461.510 (7)C134—C3371.407 (13)
C45—H4511.016C135—H13520.955
C45—H4521.014C135—H13510.940
C46—C471.504 (9)C135—H13530.957
C46—H4621.010C136—H13620.979
C46—H4611.008C136—H13610.968
C47—H4710.983C136—H13630.996
C47—H4731.011C137—H13710.978
C47—H4720.993C137—H13730.977
C48—C491.495 (6)C137—H13720.982
C48—H4811.018C335—H33510.973
C48—H4820.993C335—H33530.971
C49—C501.511 (7)C335—H33520.944
C49—H4921.008C336—H33610.953
C49—H4911.005C336—H33620.950
C50—H5010.985C336—H33631.003
C50—H5021.003C337—H33721.035
C50—H5030.986C337—H33710.866
C51—C521.527 (6)C337—H33731.085
C51—C531.539 (6)O6—C1071.439 (15)
C51—C541.536 (6)O6—C2071.426 (11)
C52—H5220.981C107—C1081.544 (16)
C52—H5210.985C107—H10721.037
C52—H5230.996C107—H10711.013
C53—H5320.976C108—C1091.422 (15)
C53—H5310.987C108—H10810.980
C53—H5330.983C108—H10820.975
C54—H5430.988C109—H10930.942
C54—H5421.002C109—H10921.002
C54—H5410.982C109—H10910.979
C55—C561.515 (7)C207—C2081.532 (12)
C55—C571.511 (6)C207—H20720.957
C55—C581.527 (7)C207—H20711.002
C56—H5630.984C208—C2091.500 (12)
C56—H5620.988C208—H20811.018
C56—H5610.973C208—H20820.983
C57—H5710.977C209—H20930.970
C57—H5720.984C209—H20920.958
C57—H5730.982C209—H20910.955
C58—H5820.975C138—C1391.532 (9)
C58—H5811.001C138—C1401.524 (9)
C58—H5830.990C138—C1411.517 (9)
C59—C601.526 (7)C139—H13930.983
C59—C611.523 (7)C139—H13920.977
C59—C621.539 (6)C139—H13910.986
C60—H6021.000C140—H14010.981
C60—H6010.988C140—H14020.995
C60—H6031.002C140—H14030.971
C61—H6130.976C141—H14120.967
C61—H6120.968C141—H14110.995
C61—H6111.003C141—H14130.989
C62—H6230.975C338—C3391.53 (2)
C62—H6220.991C338—C3401.53 (2)
C62—H6210.993C338—C3411.53 (2)
C63—C641.544 (6)C339—H33921.110
C63—C651.524 (6)C339—H33911.129
C63—C661.529 (6)C339—H33931.123
C64—H6410.994C340—H34030.997
C64—H6420.984C340—H34020.993
C64—H6431.003C340—H34010.879
C65—H6520.997C341—H34130.971
C65—H6510.998C341—H34120.926
C65—H6530.977C341—H34111.012
C66—H6620.990C67—C681.545 (11)
C66—H6610.989C67—C691.548 (12)
C66—H6630.983C67—C701.533 (12)
C71—H7121.009C68—H6810.977
C71—H7111.031C68—H6820.950
C72—C731.518 (5)C68—H6831.004
C72—C1011.399 (5)C69—H6920.966
C72—C1061.391 (5)C69—H6910.995
C73—C741.527 (5)C69—H6930.963
C73—H7310.997C70—H7020.983
C73—H7321.006C70—H7010.984
C74—C751.388 (5)C70—H7030.937
C74—C1021.395 (5)C267—C2681.529 (17)
C75—C761.397 (6)C267—C2691.520 (17)
C75—H7510.978C267—C2701.533 (17)
C76—C771.394 (6)C268—H26830.919
C76—C1221.531 (5)C268—H26821.018
C77—C781.400 (5)C268—H26811.018
C77—H7710.962C269—H26930.934
C78—C791.516 (5)C269—H26920.976
C78—C1021.385 (5)C269—H26910.995
C79—C801.523 (5)C270—H27010.942
C79—H7910.993C270—H27021.026
C79—H7921.016C270—H27030.968
C80—C811.388 (5)C36—C371.494 (10)
C80—C1031.396 (5)C36—H3620.992
C81—C821.389 (6)C36—H3611.002
C81—H8110.968C37—C381.506 (8)
C82—C831.382 (6)C37—H3721.006
C82—C1261.533 (5)C37—H3710.996
C83—C841.399 (5)C38—H3810.982
C83—H8310.964C38—H3820.969
C84—C851.526 (5)C38—H3830.983
C84—C1031.404 (5)C236—C2371.509 (18)
C85—C861.527 (5)C236—H23620.970
C85—H8511.007C236—H23611.024
C85—H8521.019C237—C2381.512 (16)
C86—C871.407 (5)C237—H23720.948
C86—C1041.398 (5)C237—H23710.940
C87—C881.387 (5)C238—H23810.972
C87—H8710.973C238—H23820.955
C88—C891.384 (5)C238—H23831.003
C88—C1301.537 (5)
C31—O1—C36115.7 (4)C98—C97—H972108.5
C31—O1—C236105.8 (9)C96—C97—H971109.5
C32—O2—C39113.6 (3)C98—C97—H971108.4
C33—O3—C42115.0 (3)H972—C97—H971108.1
C34—O4—C45113.1 (3)C97—C98—C99121.0 (4)
C35—O5—C48113.2 (3)C97—C98—C106120.6 (4)
C103—O7—C110114.5 (3)C99—C98—C106118.5 (4)
C104—O8—C113112.9 (3)C98—C99—C100122.4 (4)
C105—O9—C116112.3 (3)C98—C99—H991118.0
C106—O10—C119114.7 (3)C100—C99—H991119.6
C2—C1—C30121.5 (4)C99—C100—C101117.1 (4)
C2—C1—C35120.9 (4)C99—C100—C138121.3 (4)
C30—C1—C35117.4 (4)C101—C100—C138121.7 (4)
C1—C2—C3115.8 (3)C99—C100—C101117.1 (4)
C1—C2—H21109.1C99—C100—C338122.4 (12)
C3—C2—H21108.1C101—C100—C338120.2 (11)
C1—C2—H22108.7C72—C101—C100122.8 (4)
C3—C2—H22107.5C72—C101—H1011118.2
H21—C2—H22107.4C100—C101—H1011119.0
C2—C3—C4120.6 (4)C74—C102—C78121.6 (4)
C2—C3—C31121.5 (4)C74—C102—O6119.7 (4)
C4—C3—C31117.8 (4)C78—C102—O6118.6 (3)
C3—C4—C5122.9 (4)C84—C103—O7119.6 (3)
C3—C4—H41119.2C84—C103—C80121.4 (3)
C5—C4—H41117.9O7—C103—C80118.7 (3)
C4—C5—C6116.7 (4)C90—C104—C86121.3 (3)
C4—C5—C51122.4 (4)C90—C104—O8118.0 (3)
C6—C5—C51120.8 (4)C86—C104—O8120.7 (3)
C5—C6—C7123.2 (4)C92—C105—O9118.5 (3)
C5—C6—H61119.1C92—C105—C96121.6 (3)
C7—C6—H61117.7O9—C105—C96119.9 (3)
C6—C7—C8120.5 (4)C98—C106—O10118.1 (4)
C6—C7—C31117.8 (4)C98—C106—C72121.2 (4)
C8—C7—C31121.6 (4)O10—C106—C72120.6 (4)
C7—C8—C9116.3 (3)O7—C110—C111108.2 (3)
C7—C8—H81108.2O7—C110—H1101109.2
C9—C8—H81107.4C111—C110—H1101111.0
C7—C8—H82108.3O7—C110—H1102109.2
C9—C8—H82107.5C111—C110—H1102111.0
H81—C8—H82108.9H1101—C110—H1102108.2
C8—C9—C10120.1 (4)C110—C111—C112109.9 (4)
C8—C9—C32122.2 (4)C110—C111—H1112107.7
C10—C9—C32117.7 (4)C112—C111—H1112110.9
C9—C10—C11123.2 (4)C110—C111—H1111109.2
C9—C10—H101118.5C112—C111—H1111110.7
C11—C10—H101118.3H1112—C111—H1111108.3
C10—C11—C12116.2 (4)C111—C112—H1123110.9
C10—C11—C55121.6 (4)C111—C112—H1122110.5
C12—C11—C55122.2 (4)H1123—C112—H1122107.0
C11—C12—C13122.9 (4)C111—C112—H1121112.1
C11—C12—H121119.2H1123—C112—H1121108.8
C13—C12—H121117.9H1122—C112—H1121107.4
C12—C13—C14120.3 (4)O8—C113—C114109.1 (3)
C12—C13—C32118.0 (4)O8—C113—H1131110.4
C14—C13—C32121.7 (4)C114—C113—H1131111.2
C13—C14—C15114.8 (3)O8—C113—H1132109.7
C13—C14—H141107.7C114—C113—H1132108.5
C15—C14—H141108.3H1131—C113—H1132107.8
C13—C14—H142108.2C113—C114—C115111.6 (4)
C15—C14—H142109.3C113—C114—H1142109.0
H141—C14—H142108.4C115—C114—H1142109.0
C14—C15—C16119.9 (4)C113—C114—H1141108.5
C14—C15—C33121.1 (4)C115—C114—H1141110.5
C16—C15—C33119.1 (4)H1142—C114—H1141108.1
C15—C16—C17122.0 (4)C114—C115—H1153111.1
C15—C16—H161118.7C114—C115—H1152110.8
C17—C16—H161119.3H1153—C115—H1152109.2
C16—C17—C18117.0 (4)C114—C115—H1151108.6
C16—C17—C59122.8 (4)H1153—C115—H1151108.8
C18—C17—C59120.2 (4)H1152—C115—H1151108.4
C17—C18—C19123.3 (4)O9—C116—C117108.9 (3)
C17—C18—H181118.8O9—C116—H1161110.0
C19—C18—H181118.0C117—C116—H1161110.9
C18—C19—C20119.9 (4)O9—C116—H1162108.8
C18—C19—C33118.0 (4)C117—C116—H1162109.5
C20—C19—C33122.1 (4)H1161—C116—H1162108.8
C19—C20—C21112.6 (3)C116—C117—C118113.4 (4)
C19—C20—H202109.3C116—C117—H1171108.6
C21—C20—H202108.1C118—C117—H1171108.2
C19—C20—H201109.3C116—C117—H1172110.3
C21—C20—H201109.4C118—C117—H1172109.1
H202—C20—H201108.0H1171—C117—H1172107.0
C20—C21—C22120.8 (4)C117—C118—H1182110.7
C20—C21—C34121.5 (4)C117—C118—H1181109.9
C22—C21—C34117.8 (4)H1182—C118—H1181109.1
C21—C22—C23123.3 (4)C117—C118—H1183109.2
C21—C22—H221118.5H1182—C118—H1183109.5
C23—C22—H221118.3H1181—C118—H1183108.4
C22—C23—C24116.6 (4)O10—C119—C120108.9 (3)
C22—C23—C63120.0 (4)O10—C119—H1192110.0
C24—C23—C63123.3 (4)C120—C119—H1192110.1
C23—C24—C25122.1 (4)O10—C119—H1191109.0
C23—C24—H241119.4C120—C119—H1191110.3
C25—C24—H241118.5H1192—C119—H1191108.5
C24—C25—C26119.2 (4)C119—C120—C121114.0 (4)
C24—C25—C34118.3 (4)C119—C120—H1201108.9
C26—C25—C34122.5 (4)C121—C120—H1201108.2
C25—C26—C27117.6 (3)C119—C120—H1202108.3
C25—C26—H261107.6C121—C120—H1202110.2
C27—C26—H261106.1H1201—C120—H1202107.1
C25—C26—H262107.3C120—C121—H1212111.1
C27—C26—H262108.9C120—C121—H1211109.4
H261—C26—H262109.0H1212—C121—H1211108.4
C26—C27—C28119.6 (4)C120—C121—H1213109.3
C26—C27—C35121.7 (4)H1212—C121—H1213110.1
C28—C27—C35118.6 (4)H1211—C121—H1213108.4
C27—C28—C29122.8 (4)C76—C122—C123108.5 (4)
C27—C28—H281118.6C76—C122—C124112.4 (4)
C29—C28—H281118.6C123—C122—C124108.6 (4)
C28—C29—C30116.7 (4)C76—C122—C125110.8 (4)
C28—C29—C267121.4 (8)C123—C122—C125108.3 (4)
C30—C29—C267121.8 (8)C124—C122—C125108.2 (4)
C28—C29—C30116.7 (4)C122—C123—H1232110.0
C28—C29—C67122.5 (5)C122—C123—H1231109.5
C30—C29—C67120.9 (5)H1232—C123—H1231109.0
C1—C30—C29123.1 (4)C122—C123—H1233110.5
C1—C30—H301118.5H1232—C123—H1233109.9
C29—C30—H301118.3H1231—C123—H1233107.9
C7—C31—O1118.0 (3)C122—C124—H1241109.5
C7—C31—C3121.5 (4)C122—C124—H1243110.0
O1—C31—C3120.5 (3)H1241—C124—H1243110.7
C9—C32—O2118.9 (3)C122—C124—H1242109.3
C9—C32—C13121.6 (4)H1241—C124—H1242108.4
O2—C32—C13119.5 (4)H1243—C124—H1242108.9
C15—C33—C19120.7 (4)C122—C125—H1251110.0
C15—C33—O3119.2 (4)C122—C125—H1253108.8
C19—C33—O3119.8 (4)H1251—C125—H1253108.4
O4—C34—C21119.3 (4)C122—C125—H1252110.7
O4—C34—C25118.9 (4)H1251—C125—H1252109.2
C21—C34—C25121.7 (4)H1253—C125—H1252109.6
C1—C35—C27121.4 (4)C82—C126—C127109.2 (4)
C1—C35—O5120.0 (4)C82—C126—C128112.5 (4)
C27—C35—O5118.5 (4)C127—C126—C128108.0 (4)
O2—C39—C40114.3 (4)C82—C126—C129108.8 (4)
O2—C39—H392109.3C127—C126—C129109.0 (4)
C40—C39—H392109.0C128—C126—C129109.2 (4)
O2—C39—H391106.7C126—C127—H1271110.8
C40—C39—H391108.3C126—C127—H1272109.3
H392—C39—H391109.0H1271—C127—H1272108.6
C39—C40—C41113.8 (5)C126—C127—H1273111.0
C39—C40—H401107.6H1271—C127—H1273109.3
C41—C40—H401108.9H1272—C127—H1273107.8
C39—C40—H402109.2C126—C128—H1282110.2
C41—C40—H402108.5C126—C128—H1281110.2
H401—C40—H402108.7H1282—C128—H1281109.7
C40—C41—H413111.0C126—C128—H1283109.9
C40—C41—H412110.7H1282—C128—H1283107.6
H413—C41—H412110.1H1281—C128—H1283109.2
C40—C41—H411108.5C126—C129—H1292109.5
H413—C41—H411108.6C126—C129—H1291109.0
H412—C41—H411107.8H1292—C129—H1291108.6
O3—C42—C43109.5 (4)C126—C129—H1293111.0
O3—C42—H422107.0H1292—C129—H1293109.4
C43—C42—H422111.6H1291—C129—H1293109.3
O3—C42—H421110.6C88—C130—C131108.9 (3)
C43—C42—H421110.5C88—C130—C132109.4 (3)
H422—C42—H421107.6C131—C130—C132109.4 (4)
C42—C43—C44116.9 (6)C88—C130—C133112.8 (3)
C42—C43—H431109.6C131—C130—C133109.0 (4)
C44—C43—H431106.0C132—C130—C133107.1 (4)
C42—C43—H432109.9C130—C131—H1311111.8
C44—C43—H432105.9C130—C131—H1313109.8
H431—C43—H432108.1H1311—C131—H1313107.6
C43—C44—H441110.8C130—C131—H1312109.6
C43—C44—H443105.6H1311—C131—H1312108.7
H441—C44—H443108.1H1313—C131—H1312109.3
C43—C44—H442109.1C130—C132—H1321111.4
H441—C44—H442112.7C130—C132—H1323110.7
H443—C44—H442110.2H1321—C132—H1323107.7
O4—C45—C46108.8 (4)C130—C132—H1322109.8
O4—C45—H451111.5H1321—C132—H1322107.9
C46—C45—H451110.2H1323—C132—H1322109.3
O4—C45—H452108.7C130—C133—H1331111.1
C46—C45—H452110.0C130—C133—H1332111.3
H451—C45—H452107.7H1331—C133—H1332108.6
C45—C46—C47111.8 (5)C130—C133—H1333109.5
C45—C46—H462110.5H1331—C133—H1333108.4
C47—C46—H462108.7H1332—C133—H1333107.8
C45—C46—H461108.8C94—C134—C135107.4 (4)
C47—C46—H461108.8C94—C134—C136117.2 (5)
H462—C46—H461108.1C135—C134—C136107.6 (6)
C46—C47—H471110.6C94—C134—C137110.0 (4)
C46—C47—H473109.2C135—C134—C137102.6 (5)
H471—C47—H473108.9C136—C134—C137110.9 (6)
C46—C47—H472110.4C94—C134—C335106.3 (6)
H471—C47—H472109.4C94—C134—C336104.2 (6)
H473—C47—H472108.3C335—C134—C33696.3 (9)
O5—C48—C49109.3 (4)C94—C134—C337115.0 (7)
O5—C48—H481109.5C335—C134—C337123.9 (11)
C49—C48—H481109.4C336—C134—C337107.8 (10)
O5—C48—H482111.4C134—C135—H1352110.9
C49—C48—H482109.7C134—C135—H1351109.9
H481—C48—H482107.5H1352—C135—H1351108.2
C48—C49—C50109.6 (4)C134—C135—H1353109.9
C48—C49—H492110.0H1352—C135—H1353108.5
C50—C49—H492110.2H1351—C135—H1353109.4
C48—C49—H491108.7C134—C136—H1362111.2
C50—C49—H491109.8C134—C136—H1361110.4
H492—C49—H491108.6H1362—C136—H1361110.3
C49—C50—H501110.3C134—C136—H1363109.2
C49—C50—H502109.6H1362—C136—H1363107.1
H501—C50—H502107.8H1361—C136—H1363108.5
C49—C50—H503109.7C134—C137—H1371110.6
H501—C50—H503110.5C134—C137—H1373111.3
H502—C50—H503109.0H1371—C137—H1373110.5
C5—C51—C52112.4 (3)C134—C137—H1372107.9
C5—C51—C53108.7 (4)H1371—C137—H1372107.7
C52—C51—C53107.5 (4)H1373—C137—H1372108.7
C5—C51—C54109.9 (4)C134—C335—H3351109.7
C52—C51—C54108.9 (4)C134—C335—H3353108.0
C53—C51—C54109.4 (4)H3351—C335—H3353108.4
C51—C52—H522110.5C134—C335—H3352110.5
C51—C52—H521109.0H3351—C335—H3352110.1
H522—C52—H521109.0H3353—C335—H3352110.1
C51—C52—H523110.4C134—C336—H3361111.6
H522—C52—H523108.7C134—C336—H3362111.2
H521—C52—H523109.2H3361—C336—H3362110.4
C51—C53—H532110.4C134—C336—H3363108.6
C51—C53—H531110.2H3361—C336—H3363107.6
H532—C53—H531108.1H3362—C336—H3363107.2
C51—C53—H533110.0C134—C337—H3372108.6
H532—C53—H533109.6C134—C337—H3371120.5
H531—C53—H533108.5H3372—C337—H3371113.4
C51—C54—H543109.9C134—C337—H3373105.0
C51—C54—H542110.0H3372—C337—H337397.7
H543—C54—H542108.4H3371—C337—H3373108.7
C51—C54—H541109.6C102—O6—C107113.0 (9)
H543—C54—H541109.7C102—O6—C207114.2 (5)
H542—C54—H541109.2O6—C107—C108112.6 (15)
C11—C55—C56108.1 (4)O6—C107—H1072107.3
C11—C55—C57112.8 (4)C108—C107—H1072110.9
C56—C55—C57110.5 (5)O6—C107—H1071110.6
C11—C55—C58111.4 (4)C108—C107—H1071111.9
C56—C55—C58107.3 (5)H1072—C107—H1071103.1
C57—C55—C58106.6 (4)C107—C108—C10999.5 (17)
C55—C56—H563109.8C107—C108—H1081109.8
C55—C56—H562107.7C109—C108—H1081115.8
H563—C56—H562108.9C107—C108—H1082109.7
C55—C56—H561109.8C109—C108—H1082110.6
H563—C56—H561110.9H1081—C108—H1082110.9
H562—C56—H561109.7C108—C109—H1093107.2
C55—C57—H571111.0C108—C109—H1092108.1
C55—C57—H572109.7H1093—C109—H1092110.0
H571—C57—H572108.2C108—C109—H1091112.2
C55—C57—H573111.6H1093—C109—H1091112.2
H571—C57—H573108.9H1092—C109—H1091107.1
H572—C57—H573107.3O6—C207—C208104.1 (8)
C55—C58—H582109.5O6—C207—H2072112.4
C55—C58—H581109.4C208—C207—H2072111.3
H582—C58—H581110.6O6—C207—H2071111.9
C55—C58—H583109.7C208—C207—H2071106.6
H582—C58—H583109.6H2072—C207—H2071110.3
H581—C58—H583108.0C207—C208—C209110.5 (10)
C17—C59—C60112.1 (4)C207—C208—H2081112.6
C17—C59—C61109.7 (5)C209—C208—H2081106.4
C60—C59—C61108.5 (5)C207—C208—H2082110.6
C17—C59—C62109.2 (4)C209—C208—H2082111.2
C60—C59—C62106.7 (5)H2081—C208—H2082105.3
C61—C59—C62110.5 (4)C208—C209—H2093110.0
C59—C60—H602108.4C208—C209—H2092109.9
C59—C60—H601111.8H2093—C209—H2092109.6
H602—C60—H601108.8C208—C209—H2091109.0
C59—C60—H603111.1H2093—C209—H2091110.0
H602—C60—H603108.1H2092—C209—H2091108.4
H601—C60—H603108.6C100—C138—C139107.9 (6)
C59—C61—H613109.6C100—C138—C140110.2 (6)
C59—C61—H612110.7C139—C138—C140108.9 (7)
H613—C61—H612110.8C100—C138—C141112.7 (6)
C59—C61—H611108.3C139—C138—C141108.7 (8)
H613—C61—H611108.8C140—C138—C141108.5 (7)
H612—C61—H611108.5C138—C139—H1393108.5
C59—C62—H623110.1C138—C139—H1392109.7
C59—C62—H622110.0H1393—C139—H1392109.0
H623—C62—H622110.0C138—C139—H1391109.7
C59—C62—H621111.0H1393—C139—H1391109.4
H623—C62—H621107.9H1392—C139—H1391110.5
H622—C62—H621107.8C138—C140—H1401110.2
C23—C63—C64110.4 (3)C138—C140—H1402108.6
C23—C63—C65108.1 (4)H1401—C140—H1402108.7
C64—C63—C65108.9 (4)C138—C140—H1403110.4
C23—C63—C66112.7 (4)H1401—C140—H1403108.9
C64—C63—C66108.1 (4)H1402—C140—H1403110.0
C65—C63—C66108.6 (4)C138—C141—H1412111.3
C63—C64—H641108.9C138—C141—H1411109.1
C63—C64—H642110.2H1412—C141—H1411108.3
H641—C64—H642108.7C138—C141—H1413110.4
C63—C64—H643109.9H1412—C141—H1413108.8
H641—C64—H643109.0H1411—C141—H1413108.8
H642—C64—H643110.2C100—C338—C339110 (2)
C63—C65—H652109.1C100—C338—C340111 (2)
C63—C65—H651110.3C339—C338—C340107 (2)
H652—C65—H651108.2C100—C338—C341108 (2)
C63—C65—H653110.4C339—C338—C341109 (3)
H652—C65—H653109.0C340—C338—C341111 (3)
H651—C65—H653109.8C338—C339—H3392106.5
C63—C66—H662109.8C338—C339—H3391105.7
C63—C66—H661110.5H3392—C339—H3391112.6
H662—C66—H661109.0C338—C339—H3393107.6
C63—C66—H663109.7H3392—C339—H3393112.3
H662—C66—H663108.7H3391—C339—H3393111.5
H661—C66—H663109.3C338—C340—H3403106.4
Cl2—C71—Cl1113.0 (4)C338—C340—H3402105.9
Cl2—C71—H712109.2H3403—C340—H3402104.1
Cl1—C71—H712110.4C338—C340—H3401114.0
Cl2—C71—H711108.0H3403—C340—H3401112.6
Cl1—C71—H711109.8H3402—C340—H3401113.1
H712—C71—H711106.1C338—C341—H3413110.7
C73—C72—C101119.5 (4)C338—C341—H3412112.5
C73—C72—C106122.5 (4)H3413—C341—H3412111.6
C101—C72—C106118.0 (4)C338—C341—H3411109.0
C72—C73—C74113.7 (3)H3413—C341—H3411104.8
C72—C73—H731109.0H3412—C341—H3411107.9
C74—C73—H731108.8C29—C67—C68112.9 (9)
C72—C73—H732108.2C29—C67—C69109.6 (9)
C74—C73—H732109.6C68—C67—C69107.8 (10)
H731—C73—H732107.4C29—C67—C70110.3 (9)
C73—C74—C75121.7 (4)C68—C67—C70107.6 (10)
C73—C74—C102120.4 (3)C69—C67—C70108.5 (9)
C75—C74—C102117.9 (4)C67—C68—H681109.8
C74—C75—C76122.8 (4)C67—C68—H682111.1
C74—C75—H751118.7H681—C68—H682109.7
C76—C75—H751118.4C67—C68—H683109.1
C75—C76—C77116.7 (4)H681—C68—H683108.3
C75—C76—C122119.9 (4)H682—C68—H683108.7
C77—C76—C122123.4 (4)C67—C69—H692109.4
C76—C77—C78122.4 (4)C67—C69—H691110.5
C76—C77—H771119.4H692—C69—H691109.3
C78—C77—H771118.2C67—C69—H693109.2
C77—C78—C79120.2 (4)H692—C69—H693109.9
C77—C78—C102118.0 (4)H691—C69—H693108.6
C79—C78—C102121.7 (4)C67—C70—H702109.5
C78—C79—C80117.5 (3)C67—C70—H701110.2
C78—C79—H791108.5H702—C70—H701107.6
C80—C79—H791108.6C67—C70—H703110.6
C78—C79—H792106.8H702—C70—H703109.5
C80—C79—H792107.2H701—C70—H703109.4
H791—C79—H792107.9C29—C267—C268110.5 (16)
C79—C80—C81119.7 (4)C29—C267—C269111.4 (16)
C79—C80—C103122.3 (4)C268—C267—C269104.5 (17)
C81—C80—C103117.9 (4)C29—C267—C270108.4 (15)
C80—C81—C82123.3 (4)C268—C267—C270111.2 (18)
C80—C81—H811117.5C269—C267—C270110.7 (17)
C82—C81—H811119.2C267—C268—H2683114.4
C81—C82—C83116.8 (4)C267—C268—H2682109.4
C81—C82—C126120.1 (4)H2683—C268—H2682110.6
C83—C82—C126123.1 (4)C267—C268—H2681108.0
C82—C83—C84123.3 (4)H2683—C268—H2681110.1
C82—C83—H831118.5H2682—C268—H2681103.7
C84—C83—H831118.2C267—C269—H2693112.0
C83—C84—C85121.0 (3)C267—C269—H2692106.3
C83—C84—C103117.3 (4)H2693—C269—H2692111.2
C85—C84—C103121.7 (3)C267—C269—H2691108.2
C84—C85—C86115.9 (3)H2693—C269—H2691111.2
C84—C85—H851108.3H2692—C269—H2691107.7
C86—C85—H851107.5C267—C270—H2701113.4
C84—C85—H852108.4C267—C270—H2702107.4
C86—C85—H852109.1H2701—C270—H2702106.6
H851—C85—H852107.3C267—C270—H2703109.9
C85—C86—C87120.4 (3)H2701—C270—H2703112.5
C85—C86—C104122.3 (3)H2702—C270—H2703106.6
C87—C86—C104117.3 (3)O1—C36—C37108.0 (7)
C86—C87—C88123.2 (4)O1—C36—H362110.7
C86—C87—H871118.4C37—C36—H362109.7
C88—C87—H871118.4O1—C36—H361111.3
C87—C88—C89117.5 (3)C37—C36—H361110.2
C87—C88—C130119.4 (3)H362—C36—H361106.9
C89—C88—C130123.1 (4)C36—C37—C38112.6 (6)
C88—C89—C90122.2 (4)C36—C37—H372109.3
C88—C89—H891119.1C38—C37—H372110.4
C90—C89—H891118.7C36—C37—H371109.2
C89—C90—C91119.8 (3)C38—C37—H371109.0
C89—C90—C104118.4 (3)H372—C37—H371106.2
C91—C90—C104121.6 (3)C37—C38—H381111.9
C90—C91—C92117.4 (3)C37—C38—H382110.3
C90—C91—H911108.6H381—C38—H382108.4
C92—C91—H911107.0C37—C38—H383110.5
C90—C91—H912108.5H381—C38—H383107.4
C92—C91—H912108.0H382—C38—H383108.2
H911—C91—H912106.9O1—C236—C237114.4 (17)
C91—C92—C93120.2 (3)O1—C236—H2362110.8
C91—C92—C105121.8 (3)C237—C236—H2362112.2
C93—C92—C105117.9 (3)O1—C236—H2361106.8
C92—C93—C94122.7 (4)C237—C236—H2361105.9
C92—C93—H931117.6H2362—C236—H2361106.1
C94—C93—H931119.7C236—C237—C238109.8 (17)
C93—C94—C95117.2 (3)C236—C237—H2372109.1
C93—C94—C134121.1 (4)C238—C237—H2372105.5
C95—C94—C134121.7 (4)C236—C237—H2371109.2
C94—C95—C96122.4 (4)C238—C237—H2371109.1
C94—C95—H951119.2H2372—C237—H2371113.9
C96—C95—H951118.4C237—C238—H2381110.3
C95—C96—C97119.9 (4)C237—C238—H2382113.9
C95—C96—C105118.0 (4)H2381—C238—H2382109.2
C97—C96—C105122.1 (3)C237—C238—H2383109.9
C96—C97—C98112.6 (3)H2381—C238—H2383105.8
C96—C97—H972109.6H2382—C238—H2383107.4
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C71—H711···O71.032.363.363 (8)163
C48—H482···O10.992.603.351 (5)134
C110—H1101···O81.002.573.361 (5)136
C14—H142···O21.012.392.874 (5)109
C120—H1202···O91.002.573.371 (5)136
C14—H142···O31.012.472.869 (5)103
C73—H731···O61.002.422.862 (5)106
C73—H731···O101.002.502.918 (5)105
C85—H852···O71.022.422.900 (5)108
C85—H852···O81.022.462.924 (5)107
C97—H972···O91.002.432.896 (5)107
C97—H972···O101.002.462.829 (5)101
C38—H382···Cl10.972.923.795 (5)151

Experimental details

Crystal data
Chemical formulaC70H100O5·0.5CH2Cl2
Mr1064.03
Crystal system, space groupMonoclinic, P21/c
Temperature (K)150
a, b, c (Å)12.3740 (2), 23.9130 (2), 43.6550 (5)
β (°) 91.7460 (5)
V3)12911.5 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.45 × 0.23 × 0.12
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
39073, 20282, 13395
Rint0.043
θmax (°)24.1
(sin θ/λ)max1)0.575
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.151, 1.02
No. of reflections20282
No. of parameters1531
No. of restraints220
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.88, 1.75

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR97 (Altomare et al., 1999), DIAMOND (Brandenburg & Putz, 2005), CRYSTALS (Betteridge et al., 2003) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C71—H711···O71.032.363.363 (8)163
C48—H482···O10.992.603.351 (5)134
C110—H1101···O81.002.573.361 (5)136
C120—H1202···O91.002.573.371 (5)136
C14—H142···O31.012.472.869 (5)103
C38—H382···Cl10.972.923.795 (5)151
 

Acknowledgements

The authors acknowledge the institutional research plan No. AVOZ10100521 of the Institute of Physics, the project Praemium Academiae of the Academy of Sciences of the Czech Republic and the Czech Ministry of Education, Youth and Sports, projects MSM6046137301 and MSM 4977751303.

References

First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS 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 citationBrandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.  Google Scholar
First citationPrince, E. (1982). Mathematical Techniques in Crystallography and Materials Science. New York: Springer-Verlag.  Google Scholar
First citationStewart, D. R., Krawiec, M., Kashyap, R. P., Watson, W. H. & Gutsche, C. D. (1995). J. Am. Chem. Soc. 117, 586–601.  CSD CrossRef CAS Web of Science Google Scholar
First citationWatkin, D. (1994). Acta Cryst. A50, 411–437.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 2| February 2011| Pages o296-o297
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