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

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ISSN: 2056-9890

5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetra­meth­oxy­calix[4]arene di­chloro­methane hemisolvate

aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
*Correspondence e-mail: edwin.weber@chemie.tu-freiberg.de

(Received 11 December 2007; accepted 22 January 2008; online 5 March 2008)

In the title compound, C48H64O4·0.5CH2Cl2, both crystallographically independent calixarene mol­ecules display a partial cone conformation. Their crystal packing is stabilized by C—H⋯π contacts involving the meth­oxy groups. The solvent mol­ecule is located inter­stitially between two calixarene units with C—H⋯Cl contacts to meth­oxy and tert-butyl groups. One tert-butyl residue of each calixarene mol­ecule is disordered over two positions (occupancies 0.60/0.40 and 0.63/0.37), resulting in bond distances that deviate from ideal values. The tetra­mer calixarene mol­ecules present models with approximate non-crystallographic Cs symmetry.

Related literature

The solvent-free title compound has been described to assume a partial cone conformation (Grootenhuis et al., 1990[Grootenhuis, P. D. J., Kollman, P. A., Groenen, L. C., Reinhoudt, D. N., van Hummel, G. J., Ugozzoli, F. & Andreetti, G. D. (1990). J. Am. Chem. Soc. 112, 4165-4176.]). A closely related solvate with THF has been described previously (Fischer et al., 2007[Fischer, C., Gruber, T., Seichter, W. & Weber, E. (2007). Acta Cryst. E63, o4572-o4573.], and literature cited therein). For the synthesis of the compound, see: Bitter et al. (1995[Bitter, I., Grün, A., Ágai, B. & Tôke, L. (1995). Tetrahedron, 51, 7835-7840.]). For other related literature, see: Gutsche et al. (1983[Gutsche, C. D., Dhawan, B., Levine, J. A., No, K. H. & Bauer, L. J. (1983). Tetrahedron, 39, 409-426.]), Iwamoto et al. (1991[Iwamoto, K., Araki, K. & Shinkai, S. (1991). J. Org. Chem. 56, 4955-4962.]); Nishio (2004[Nishio, M. (2004). CrystEngComm, 6, 130-158.]).

[Scheme 1]

Experimental

Crystal data
  • C48H64O4·0.5CH2Cl2

  • Mr = 747.46

  • Monoclinic, P 21 /c

  • a = 16.7012 (6) Å

  • b = 19.7113 (8) Å

  • c = 28.2577 (11) Å

  • β = 103.097 (2)°

  • V = 9060.5 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 133 (2) K

  • 0.60 × 0.60 × 0.60 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.929, Tmax = 0.929

  • 186561 measured reflections

  • 20781 independent reflections

  • 12758 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.073

  • wR(F2) = 0.272

  • S = 1.21

  • 20781 reflections

  • 1058 parameters

  • H-atom parameters constrained

  • Δρmax = 0.82 e Å−3

  • Δρmin = −1.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C33A—H33E⋯Cl1Gi 0.98 2.92 3.711 (3) 139
C46—H46A⋯Cl2Gii 0.98 2.89 3.551 (10) 126
C7A—H7A1⋯CgCi 0.99 2.88 3.733 (2) 145
C33—H33ACgA′iii 0.98 2.74 3.549 (3) 140
C48—H48ACgC′ 0.98 2.76 3.526 (3) 136
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+2; (iii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]. CgC is the centroid of atoms C15–C20, CgA′ is the centroid of atoms C1A–C6A and CgC′ is the centroid of atoms C15A–C20A.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-NT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The molecular geometry of the calixarene (Figure 1) is best described by a partial cone conformation with opposite arene rings A and C differing only little from coplanarity [5.6 (1) and 9.2 (1)°, respectively], whereas the aromatic rings B and D include dihedral angles of 54.9 (1) and 58.4 (1)°, respectively. The solvent molecules are everything but located inside of the calixarene cavity offering not enough space for an accommodation. Hence the CH2Cl2 molecule occupies interstitial lattice space between two calixarene molecules (Figure 2). Due to their hydrophobic surface, the packing of the calixarene molecules is primary stabilized by van-der-Waals interactions and weak C—H···π contacts (Nishio, 2004) involving methoxy groups and neighboring aromatic rings, with H···π (centroid of the aromatic ring) distances ranging from 2.64 to 2.93 Å. Furthermore, weak C—H···Cl interactions including one of the methoxy groups [d(C33A···Cl1G) = 3.6554 Å] and a tert-butyl group [d(C46···Cl2G) = 3.4833 Å] can be observed (Table 1). The tert-butyl residues are partially disordered over two positions [0.60/0.40 (ring D), 0.63/0.37 (ring B')], resulting in bond distances that deviate from ideal values.

Related literature top

The solvent-free title compound has been described to assume a partial cone conformation (Grootenhuis et al., 1990). A closely related solvate with THF has been described previously (Fischer et al., 2007, and literature cited therein). For the synthesis of the compound, see: Bitter et al., 1995. For other related literature, see: Gutsche et al. (1983), Iwamoto et al. (1991)); Nishio (2004). CgC is the centroid of atoms C15–C20, CgA' is the centroid of atoms C1A–C6A and CgC' is the centroid of atoms C15A–C20A.

Experimental top

The title calixarene was sythesized from 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrahydroxycalix[4]arene following the literature procedure (Bitter et al., 1995). Colourless prisms of the solvated calixarene suitable for X-ray diffraction were obtained by recrystallization from dichloromethane (m.p. 515–517 K).

Refinement top

The H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 Å, and Uiso(H) = 1.2–1.5 times Ueq (parent atom).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-NT (Bruker, 2004); data reduction: SAINT-NT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular presentation of the title compound with CH2Cl2 as guest.
[Figure 2] Fig. 2. Packing diagram, viewed down the b axis. H atoms have been omitted for clarity.
5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetramethoxycalix[4]arene dichloromethane hemisolvate top
Crystal data top
C48H64O4·0.5CH2Cl2Z = 8
Mr = 747.46F(000) = 3240
Monoclinic, P21/cDx = 1.096 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 16.7012 (6) ŵ = 0.12 mm1
b = 19.7113 (8) ÅT = 133 K
c = 28.2577 (11) ÅIrregular, colourless
β = 103.097 (2)°0.60 × 0.60 × 0.60 mm
V = 9060.5 (6) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
20781 independent reflections
Radiation source: fine-focus sealed tube12758 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ϕ and ω scansθmax = 27.5°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 2119
Tmin = 0.929, Tmax = 0.929k = 2525
186561 measured reflectionsl = 3636
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.272H-atom parameters constrained
S = 1.21 w = 1/[σ2(Fo2) + (0.1495P)2 + 1.8277P]
where P = (Fo2 + 2Fc2)/3
20781 reflections(Δ/σ)max = 0.040
1058 parametersΔρmax = 0.83 e Å3
0 restraintsΔρmin = 1.13 e Å3
Crystal data top
C48H64O4·0.5CH2Cl2V = 9060.5 (6) Å3
Mr = 747.46Z = 8
Monoclinic, P21/cMo Kα radiation
a = 16.7012 (6) ŵ = 0.12 mm1
b = 19.7113 (8) ÅT = 133 K
c = 28.2577 (11) Å0.60 × 0.60 × 0.60 mm
β = 103.097 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
20781 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
12758 reflections with I > 2σ(I)
Tmin = 0.929, Tmax = 0.929Rint = 0.051
186561 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0730 restraints
wR(F2) = 0.272H-atom parameters constrained
S = 1.21Δρmax = 0.83 e Å3
20781 reflectionsΔρmin = 1.13 e Å3
1058 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.60280 (10)0.76526 (9)0.76127 (6)0.0273 (4)
O20.42283 (10)0.73542 (8)0.71821 (6)0.0265 (4)
O30.34908 (10)0.62305 (9)0.76518 (6)0.0280 (4)
O40.57295 (11)0.54128 (9)0.72312 (6)0.0311 (4)
C10.60986 (14)0.74154 (12)0.71608 (9)0.0238 (5)
C20.65502 (14)0.68252 (13)0.71359 (9)0.0252 (5)
C30.66089 (15)0.65863 (14)0.66799 (9)0.0293 (5)
H30.69130.61840.66600.035*
C40.62337 (16)0.69217 (14)0.62514 (9)0.0302 (6)
C50.57696 (16)0.74944 (13)0.62940 (9)0.0296 (6)
H50.55000.77260.60070.035*
C60.56842 (15)0.77421 (12)0.67407 (9)0.0252 (5)
C70.51028 (16)0.83291 (13)0.67603 (10)0.0302 (6)
H7A0.51390.84600.71030.036*
H7B0.52640.87260.65880.036*
C80.38253 (15)0.76378 (12)0.67482 (9)0.0243 (5)
C90.42270 (15)0.81254 (12)0.65258 (9)0.0267 (5)
C100.38306 (16)0.83698 (13)0.60731 (10)0.0316 (6)
H100.40940.87100.59240.038*
C110.30530 (16)0.81335 (13)0.58257 (10)0.0309 (6)
C120.26764 (15)0.76518 (13)0.60595 (10)0.0296 (6)
H120.21470.74890.59020.035*
C130.30470 (15)0.73966 (12)0.65185 (9)0.0257 (5)
C140.26261 (15)0.68638 (13)0.67634 (10)0.0287 (5)
H14C0.20460.68200.65850.034*
H14D0.26310.70110.70990.034*
C150.34700 (14)0.58927 (11)0.72173 (9)0.0232 (5)
C160.30485 (14)0.61746 (12)0.67787 (9)0.0236 (5)
C170.30437 (15)0.58322 (13)0.63478 (9)0.0278 (5)
H170.27570.60250.60490.033*
C180.34481 (16)0.52136 (13)0.63419 (10)0.0304 (6)
C190.38780 (16)0.49575 (12)0.67860 (10)0.0284 (5)
H190.41620.45390.67900.034*
C200.39083 (14)0.52889 (12)0.72225 (9)0.0236 (5)
C210.44439 (16)0.50240 (13)0.76944 (10)0.0293 (6)
H21C0.40940.49370.79280.035*
H21D0.46910.45870.76300.035*
C220.57354 (14)0.56945 (12)0.76836 (9)0.0243 (5)
C230.51265 (14)0.55093 (12)0.79241 (9)0.0254 (5)
C240.51367 (16)0.58064 (14)0.83718 (10)0.0302 (6)
H240.47270.56800.85400.036*
C250.57315 (16)0.62863 (14)0.85844 (9)0.0316 (6)
C260.63137 (16)0.64655 (14)0.83222 (9)0.0293 (5)
H260.67170.67960.84550.035*
C270.63274 (14)0.61798 (12)0.78739 (9)0.0242 (5)
C280.69414 (15)0.64219 (14)0.75891 (9)0.0274 (5)
H28C0.72280.60230.74920.033*
H28D0.73590.67090.78030.033*
C290.6327 (2)0.66758 (17)0.57503 (10)0.0466 (8)
C300.6708 (4)0.5982 (3)0.57684 (15)0.1008 (19)
H30A0.72550.59900.59870.151*
H30B0.67570.58500.54420.151*
H30C0.63610.56530.58880.151*
C310.6929 (4)0.7179 (3)0.55764 (17)0.1027 (19)
H31A0.67340.76450.55930.154*
H31B0.69500.70730.52410.154*
H31C0.74810.71340.57860.154*
C320.5536 (3)0.6726 (3)0.53776 (14)0.0903 (16)
H32A0.51280.64240.54680.135*
H32B0.56250.65910.50600.135*
H32C0.53350.71940.53610.135*
C330.66670 (17)0.81078 (14)0.78376 (10)0.0335 (6)
H33A0.72020.79130.78250.050*
H33B0.66420.81800.81770.050*
H33C0.65960.85430.76650.050*
C340.26726 (19)0.84015 (16)0.53167 (11)0.0418 (7)
C350.3259 (2)0.8256 (2)0.49815 (12)0.0536 (9)
H35A0.37780.84970.51010.080*
H35B0.30080.84090.46510.080*
H35C0.33650.77670.49780.080*
C360.2521 (2)0.91672 (18)0.53399 (14)0.0592 (10)
H36A0.20990.92510.55240.089*
H36B0.23350.93460.50100.089*
H36C0.30330.93940.55010.089*
C370.1848 (2)0.8052 (2)0.50887 (13)0.0614 (10)
H37A0.19340.75610.50730.092*
H37B0.16360.82290.47600.092*
H37C0.14510.81440.52880.092*
C380.41349 (18)0.77014 (15)0.76099 (10)0.0354 (6)
H38D0.43610.81610.76130.053*
H38E0.44300.74540.78980.053*
H38F0.35500.77280.76130.053*
C390.3431 (2)0.48364 (16)0.58658 (11)0.0442 (7)
C400.3160 (5)0.5286 (3)0.54277 (16)0.123 (3)
H40A0.35020.56950.54660.185*
H40B0.25840.54140.53960.185*
H40C0.32190.50400.51360.185*
C410.2830 (5)0.4240 (3)0.58312 (18)0.119 (2)
H41A0.29780.38860.56230.179*
H41B0.22700.43990.56920.179*
H41C0.28590.40550.61560.179*
C420.4238 (5)0.4509 (5)0.5877 (2)0.188 (5)
H42A0.44470.43000.61960.282*
H42B0.46300.48510.58180.282*
H42C0.41690.41590.56250.282*
C430.28403 (18)0.60501 (15)0.78743 (11)0.0371 (6)
H43A0.23130.61170.76430.056*
H43B0.28620.63360.81600.056*
H43C0.28970.55730.79730.056*
C440.57290 (18)0.66186 (17)0.90742 (10)0.0406 (7)
C45B0.5733 (5)0.7411 (3)0.9013 (2)0.063 (2)0.599 (9)
H45D0.52300.75540.87830.094*0.599 (9)
H45E0.62120.75460.88890.094*0.599 (9)
H45F0.57600.76280.93280.094*0.599 (9)
C46B0.6508 (4)0.6418 (4)0.94219 (19)0.056 (2)0.599 (9)
H46D0.65350.66380.97360.085*0.599 (9)
H46E0.69790.65610.92930.085*0.599 (9)
H46F0.65200.59250.94640.085*0.599 (9)
C47B0.4999 (5)0.6429 (6)0.9272 (3)0.086 (4)0.599 (9)
H47D0.50120.59400.93390.129*0.599 (9)
H47E0.44930.65420.90340.129*0.599 (9)
H47F0.50160.66790.95740.129*0.599 (9)
C480.61588 (19)0.47793 (16)0.72585 (13)0.0491 (8)
H48A0.67510.48590.73690.074*
H48B0.60450.45670.69370.074*
H48C0.59740.44790.74880.074*
C450.6427 (9)0.7115 (7)0.9256 (4)0.086 (5)0.401 (9)
H45A0.64890.71900.96050.129*0.401 (9)
H45B0.63040.75470.90830.129*0.401 (9)
H45C0.69390.69290.91960.129*0.401 (9)
C460.5904 (8)0.6036 (7)0.9475 (3)0.080 (4)0.401 (9)
H46A0.59850.62390.97990.121*0.401 (9)
H46B0.63990.57850.94490.121*0.401 (9)
H46C0.54340.57250.94230.121*0.401 (9)
C470.4894 (8)0.6916 (8)0.9057 (4)0.080 (5)0.401 (9)
H47A0.44730.65690.89490.121*0.401 (9)
H47B0.47980.72970.88280.121*0.401 (9)
H47C0.48670.70770.93810.121*0.401 (9)
O1A1.17566 (10)0.39965 (9)0.79774 (6)0.0261 (4)
O2A1.03065 (10)0.48985 (8)0.75598 (6)0.0253 (4)
O3A0.88555 (10)0.49010 (8)0.80712 (6)0.0271 (4)
O4A0.94633 (10)0.27854 (8)0.76393 (6)0.0263 (4)
C1A1.14831 (13)0.36509 (12)0.75435 (8)0.0222 (5)
C2A1.12314 (14)0.29761 (12)0.75532 (9)0.0238 (5)
C3A1.09746 (15)0.26289 (12)0.71166 (9)0.0251 (5)
H3A1.08220.21650.71230.030*
C4A1.09350 (14)0.29436 (13)0.66678 (9)0.0256 (5)
C5A1.11584 (15)0.36271 (13)0.66732 (9)0.0261 (5)
H5A1.11250.38540.63730.031*
C6A1.14280 (14)0.39868 (12)0.71022 (9)0.0236 (5)
C7A1.16345 (15)0.47365 (12)0.70879 (10)0.0271 (5)
H7A11.20470.47990.68900.032*
H7A21.18810.48940.74220.032*
C8A1.02534 (15)0.52380 (11)0.71257 (9)0.0231 (5)
C9A1.08823 (15)0.51668 (12)0.68767 (9)0.0253 (5)
C10A1.07839 (16)0.54748 (12)0.64226 (9)0.0271 (5)
H10A1.12130.54350.62540.033*
C11A1.00809 (16)0.58383 (12)0.62079 (9)0.0281 (5)
C12A0.94694 (16)0.58977 (12)0.64691 (9)0.0274 (5)
H12A0.89870.61470.63300.033*
C13A0.95378 (15)0.56060 (11)0.69247 (9)0.0246 (5)
C14A0.88412 (15)0.56362 (12)0.71865 (9)0.0258 (5)
H14A0.84210.59630.70190.031*
H14B0.90540.57990.75230.031*
C15A0.84881 (13)0.45960 (12)0.76320 (9)0.0214 (5)
C16A0.84482 (14)0.49415 (12)0.71992 (9)0.0226 (5)
C17A0.80957 (15)0.46159 (12)0.67593 (9)0.0258 (5)
H17A0.80580.48550.64630.031*
C18A0.78017 (14)0.39570 (12)0.67430 (9)0.0245 (5)
C19A0.78754 (14)0.36195 (12)0.71858 (9)0.0243 (5)
H19A0.76800.31670.71830.029*
C20A0.82237 (14)0.39208 (12)0.76307 (9)0.0226 (5)
C21A0.83696 (14)0.35087 (12)0.80954 (9)0.0246 (5)
H21A0.81170.30550.80220.030*
H21B0.80930.37350.83280.030*
C22A0.97906 (14)0.30570 (11)0.80969 (8)0.0219 (5)
C23A0.92743 (14)0.34220 (11)0.83324 (9)0.0220 (5)
C24A0.96146 (15)0.37132 (12)0.87778 (9)0.0254 (5)
H24A0.92640.39520.89420.031*
C25A1.04513 (15)0.36707 (12)0.89966 (9)0.0256 (5)
C26A1.09458 (15)0.33049 (12)0.87496 (9)0.0256 (5)
H26A1.15160.32620.88920.031*
C27A1.06315 (15)0.30008 (12)0.83016 (8)0.0235 (5)
C28A1.11987 (15)0.26372 (12)0.80311 (9)0.0251 (5)
H28A1.17600.26230.82410.030*
H28B1.10080.21640.79660.030*
C29A1.06832 (16)0.25501 (14)0.61851 (9)0.0324 (6)
C30A1.0112 (3)0.2970 (2)0.58006 (13)0.0701 (12)
H30D0.96680.31560.59360.105*
H30E0.98790.26830.55200.105*
H30F1.04220.33430.56980.105*
C31A1.0241 (3)0.18939 (19)0.62370 (13)0.0700 (12)
H31D0.97520.19910.63630.105*
H31E1.06090.15920.64630.105*
H31F1.00740.16730.59190.105*
C32A1.1460 (2)0.2390 (3)0.60063 (17)0.103 (2)
H32D1.13060.22320.56690.154*
H32E1.17740.20350.62110.154*
H32F1.17970.28000.60240.154*
C33A1.26088 (17)0.38840 (17)0.81930 (11)0.0430 (7)
H33D1.27310.33980.81860.064*
H33E1.27320.40430.85300.064*
H33F1.29470.41340.80100.064*
C34A0.99674 (17)0.61515 (14)0.56982 (9)0.0322 (6)
C35A0.9877 (4)0.6895 (2)0.57200 (19)0.0547 (17)0.635 (5)
H35D0.97400.70800.53890.082*0.635 (5)
H35E1.03940.70940.59000.082*0.635 (5)
H35F0.94360.70040.58850.082*0.635 (5)
C36A0.9233 (3)0.5804 (3)0.53682 (17)0.0476 (14)0.635 (5)
H36D0.91600.59810.50370.071*0.635 (5)
H36E0.87370.58930.54880.071*0.635 (5)
H36F0.93310.53130.53670.071*0.635 (5)
C37A1.0737 (3)0.6005 (3)0.54710 (16)0.0412 (12)0.635 (5)
H37D1.08280.55140.54620.062*0.635 (5)
H37E1.12260.62230.56710.062*0.635 (5)
H37F1.06330.61880.51400.062*0.635 (5)
C38A1.06639 (17)0.52777 (14)0.79879 (10)0.0324 (6)
H38A1.12320.53970.79840.049*
H38B1.06590.50030.82760.049*
H38C1.03450.56930.79970.049*
C39A0.74262 (18)0.35964 (14)0.62626 (10)0.0349 (6)
C40A0.7667 (4)0.3932 (2)0.58367 (13)0.0836 (15)
H40D0.74930.44080.58180.125*
H40E0.73990.36970.55370.125*
H40F0.82650.39080.58780.125*
C41A0.6505 (3)0.3582 (4)0.61861 (19)0.136 (3)
H41D0.63540.33700.64670.204*
H41E0.62690.33210.58930.204*
H41F0.62920.40470.61480.204*
C42A0.7712 (5)0.2869 (2)0.62814 (16)0.128 (3)
H42D0.83110.28530.63930.192*
H42E0.75500.26680.59560.192*
H42F0.74590.26130.65070.192*
C43A0.82867 (19)0.51704 (15)0.83343 (10)0.0377 (6)
H43D0.80700.56040.81900.057*
H43E0.85690.52420.86740.057*
H43F0.78330.48500.83180.057*
C44A1.07984 (17)0.40356 (14)0.94792 (10)0.0331 (6)
C45A1.0699 (2)0.48036 (17)0.93963 (13)0.0556 (9)
H45G1.09230.50430.97020.083*
H45H1.01150.49140.92830.083*
H45I1.09970.49450.91510.083*
C46A1.0315 (2)0.3829 (2)0.98586 (11)0.0531 (9)
H46G1.03230.33340.98920.080*
H46H0.97450.39850.97530.080*
H46I1.05680.40371.01720.080*
C47A1.1702 (2)0.3878 (2)0.96844 (13)0.0643 (11)
H47G1.17780.33850.97150.096*
H47H1.18810.40891.00050.096*
H47I1.20300.40570.94650.096*
C48A0.92307 (18)0.20899 (14)0.76376 (11)0.0360 (6)
H48D0.97170.18130.77690.054*
H48E0.89870.19470.73040.054*
H48F0.88280.20320.78380.054*
C35C1.0582 (5)0.6725 (4)0.5717 (3)0.040 (2)0.365 (5)
H35G1.11410.65400.57900.060*0.365 (5)
H35H1.05250.70490.59700.060*0.365 (5)
H35I1.04750.69570.54020.060*0.365 (5)
C36C0.9067 (5)0.6548 (4)0.5526 (3)0.038 (2)0.365 (5)
H36G0.90200.67440.52030.058*0.365 (5)
H36H0.90310.69100.57590.058*0.365 (5)
H36I0.86190.62230.55170.058*0.365 (5)
C37C0.9978 (7)0.5637 (5)0.5339 (3)0.053 (3)0.365 (5)
H37G0.98750.58460.50160.080*0.365 (5)
H37H0.95510.53000.53480.080*0.365 (5)
H37I1.05170.54140.54080.080*0.365 (5)
C1G0.3739 (3)0.4943 (3)0.95514 (16)0.0794 (13)
H1G10.34210.46910.97500.095*
H1G20.40550.53020.97580.095*
Cl1G0.30659 (10)0.53169 (7)0.90646 (4)0.0958 (4)
Cl2G0.44281 (10)0.43834 (9)0.93625 (6)0.1139 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0250 (9)0.0310 (9)0.0257 (9)0.0065 (7)0.0055 (7)0.0044 (7)
O20.0284 (9)0.0244 (9)0.0256 (9)0.0036 (7)0.0036 (7)0.0011 (7)
O30.0292 (9)0.0256 (9)0.0292 (9)0.0007 (7)0.0069 (7)0.0024 (7)
O40.0289 (9)0.0338 (10)0.0308 (10)0.0044 (8)0.0071 (8)0.0075 (8)
C10.0199 (11)0.0271 (12)0.0245 (12)0.0075 (9)0.0051 (9)0.0024 (10)
C20.0200 (11)0.0301 (13)0.0248 (12)0.0033 (9)0.0036 (9)0.0015 (10)
C30.0252 (12)0.0354 (14)0.0275 (13)0.0013 (10)0.0068 (10)0.0006 (11)
C40.0319 (13)0.0352 (14)0.0231 (13)0.0027 (11)0.0054 (10)0.0010 (11)
C50.0323 (13)0.0298 (13)0.0238 (13)0.0024 (11)0.0004 (10)0.0060 (10)
C60.0246 (12)0.0206 (11)0.0294 (13)0.0064 (9)0.0043 (10)0.0004 (10)
C70.0333 (14)0.0230 (12)0.0319 (14)0.0006 (10)0.0025 (11)0.0016 (10)
C80.0272 (12)0.0187 (11)0.0265 (13)0.0077 (9)0.0050 (10)0.0007 (9)
C90.0286 (13)0.0181 (11)0.0325 (14)0.0025 (9)0.0052 (10)0.0015 (10)
C100.0342 (14)0.0241 (13)0.0368 (15)0.0044 (10)0.0088 (11)0.0053 (11)
C110.0297 (13)0.0319 (14)0.0304 (14)0.0100 (11)0.0051 (11)0.0040 (11)
C120.0247 (12)0.0304 (13)0.0317 (14)0.0069 (10)0.0026 (10)0.0001 (11)
C130.0262 (12)0.0232 (12)0.0277 (13)0.0073 (9)0.0063 (10)0.0017 (10)
C140.0237 (12)0.0291 (13)0.0336 (14)0.0055 (10)0.0070 (10)0.0029 (11)
C150.0223 (11)0.0186 (11)0.0292 (13)0.0036 (9)0.0070 (10)0.0013 (9)
C160.0178 (11)0.0234 (12)0.0300 (13)0.0014 (9)0.0066 (9)0.0030 (10)
C170.0230 (12)0.0314 (13)0.0278 (13)0.0025 (10)0.0030 (10)0.0030 (10)
C180.0319 (14)0.0296 (13)0.0309 (14)0.0064 (11)0.0094 (11)0.0046 (11)
C190.0289 (13)0.0192 (11)0.0381 (15)0.0017 (10)0.0095 (11)0.0003 (10)
C200.0203 (11)0.0199 (11)0.0299 (13)0.0025 (9)0.0044 (10)0.0018 (10)
C210.0296 (13)0.0229 (12)0.0343 (14)0.0001 (10)0.0049 (11)0.0072 (11)
C220.0207 (11)0.0269 (12)0.0239 (12)0.0058 (9)0.0018 (9)0.0028 (10)
C230.0224 (12)0.0233 (12)0.0286 (13)0.0034 (9)0.0017 (10)0.0084 (10)
C240.0267 (13)0.0366 (14)0.0283 (13)0.0011 (11)0.0084 (10)0.0070 (11)
C250.0329 (14)0.0396 (15)0.0227 (13)0.0005 (11)0.0070 (11)0.0031 (11)
C260.0264 (12)0.0349 (14)0.0247 (13)0.0002 (11)0.0021 (10)0.0042 (11)
C270.0190 (11)0.0289 (13)0.0238 (12)0.0048 (9)0.0032 (9)0.0046 (10)
C280.0201 (11)0.0359 (14)0.0253 (13)0.0025 (10)0.0034 (10)0.0010 (10)
C290.059 (2)0.057 (2)0.0227 (14)0.0126 (16)0.0065 (13)0.0034 (13)
C300.166 (5)0.093 (3)0.041 (2)0.055 (4)0.018 (3)0.014 (2)
C310.145 (5)0.123 (4)0.062 (3)0.037 (4)0.068 (3)0.023 (3)
C320.089 (3)0.130 (4)0.039 (2)0.032 (3)0.010 (2)0.034 (2)
C330.0344 (14)0.0368 (15)0.0280 (14)0.0110 (11)0.0042 (11)0.0094 (11)
C340.0395 (16)0.0499 (18)0.0325 (15)0.0083 (13)0.0013 (12)0.0144 (13)
C350.054 (2)0.071 (2)0.0329 (17)0.0052 (17)0.0055 (14)0.0095 (16)
C360.069 (2)0.055 (2)0.050 (2)0.0221 (18)0.0043 (18)0.0224 (17)
C370.0460 (19)0.084 (3)0.044 (2)0.0002 (18)0.0099 (15)0.0235 (19)
C380.0385 (15)0.0366 (15)0.0312 (14)0.0012 (12)0.0078 (12)0.0053 (12)
C390.0534 (19)0.0465 (18)0.0333 (16)0.0049 (14)0.0116 (14)0.0089 (13)
C400.261 (8)0.078 (3)0.039 (2)0.040 (4)0.049 (4)0.003 (2)
C410.197 (7)0.099 (4)0.062 (3)0.067 (4)0.030 (4)0.045 (3)
C420.145 (6)0.313 (11)0.084 (4)0.144 (7)0.022 (4)0.105 (6)
C430.0424 (16)0.0355 (15)0.0375 (16)0.0018 (12)0.0177 (13)0.0010 (12)
C440.0406 (16)0.061 (2)0.0201 (13)0.0081 (14)0.0070 (11)0.0064 (13)
C45B0.089 (6)0.064 (4)0.037 (3)0.005 (4)0.018 (3)0.017 (3)
C46B0.059 (4)0.080 (5)0.028 (3)0.005 (3)0.005 (3)0.006 (3)
C47B0.065 (5)0.159 (10)0.044 (4)0.044 (6)0.030 (4)0.044 (5)
C480.0389 (17)0.0438 (18)0.066 (2)0.0078 (14)0.0152 (16)0.0164 (16)
C450.101 (10)0.108 (11)0.060 (7)0.058 (9)0.043 (7)0.044 (7)
C460.098 (10)0.114 (10)0.024 (5)0.006 (7)0.001 (5)0.001 (5)
C470.088 (8)0.117 (11)0.034 (5)0.045 (8)0.008 (5)0.025 (6)
O1A0.0248 (9)0.0285 (9)0.0243 (9)0.0001 (7)0.0036 (7)0.0053 (7)
O2A0.0272 (9)0.0242 (8)0.0241 (9)0.0002 (7)0.0052 (7)0.0053 (7)
O3A0.0273 (9)0.0249 (9)0.0278 (9)0.0003 (7)0.0036 (7)0.0031 (7)
O4A0.0336 (9)0.0222 (8)0.0209 (8)0.0011 (7)0.0020 (7)0.0011 (7)
C1A0.0168 (11)0.0277 (12)0.0213 (11)0.0036 (9)0.0028 (9)0.0025 (9)
C2A0.0222 (11)0.0260 (12)0.0234 (12)0.0072 (9)0.0057 (9)0.0015 (10)
C3A0.0257 (12)0.0216 (12)0.0274 (13)0.0035 (9)0.0049 (10)0.0000 (10)
C4A0.0230 (12)0.0294 (13)0.0230 (12)0.0015 (10)0.0023 (9)0.0025 (10)
C5A0.0236 (12)0.0343 (13)0.0198 (12)0.0020 (10)0.0035 (9)0.0047 (10)
C6A0.0182 (11)0.0262 (12)0.0271 (13)0.0027 (9)0.0068 (9)0.0001 (10)
C7A0.0228 (12)0.0294 (13)0.0299 (13)0.0029 (10)0.0078 (10)0.0030 (10)
C8A0.0252 (12)0.0181 (11)0.0257 (12)0.0035 (9)0.0050 (10)0.0028 (9)
C9A0.0256 (12)0.0206 (11)0.0296 (13)0.0062 (9)0.0063 (10)0.0013 (10)
C10A0.0325 (13)0.0234 (12)0.0263 (13)0.0094 (10)0.0085 (10)0.0016 (10)
C11A0.0399 (14)0.0204 (12)0.0228 (12)0.0096 (10)0.0043 (11)0.0023 (9)
C12A0.0309 (13)0.0192 (11)0.0295 (13)0.0033 (10)0.0015 (10)0.0017 (10)
C13A0.0272 (12)0.0149 (11)0.0304 (13)0.0040 (9)0.0038 (10)0.0001 (9)
C14A0.0278 (12)0.0199 (11)0.0301 (13)0.0037 (9)0.0075 (10)0.0050 (10)
C15A0.0169 (11)0.0214 (11)0.0248 (12)0.0017 (9)0.0025 (9)0.0001 (9)
C16A0.0182 (11)0.0212 (11)0.0283 (13)0.0034 (9)0.0051 (9)0.0029 (9)
C17A0.0258 (12)0.0265 (12)0.0247 (12)0.0048 (10)0.0049 (10)0.0057 (10)
C18A0.0218 (11)0.0256 (12)0.0256 (12)0.0023 (9)0.0042 (9)0.0022 (10)
C19A0.0196 (11)0.0220 (11)0.0311 (13)0.0018 (9)0.0056 (10)0.0019 (10)
C20A0.0175 (11)0.0245 (12)0.0261 (12)0.0004 (9)0.0055 (9)0.0019 (10)
C21A0.0225 (12)0.0232 (12)0.0287 (13)0.0022 (9)0.0072 (10)0.0023 (10)
C22A0.0286 (12)0.0164 (11)0.0193 (11)0.0007 (9)0.0027 (9)0.0031 (9)
C23A0.0240 (12)0.0179 (11)0.0244 (12)0.0021 (9)0.0058 (9)0.0074 (9)
C24A0.0304 (13)0.0213 (12)0.0266 (13)0.0020 (10)0.0106 (10)0.0026 (10)
C25A0.0299 (13)0.0264 (12)0.0201 (12)0.0005 (10)0.0047 (10)0.0013 (10)
C26A0.0241 (12)0.0263 (12)0.0244 (12)0.0013 (10)0.0012 (10)0.0022 (10)
C27A0.0284 (12)0.0215 (11)0.0210 (12)0.0026 (9)0.0063 (9)0.0038 (9)
C28A0.0252 (12)0.0235 (12)0.0259 (12)0.0056 (9)0.0047 (10)0.0023 (10)
C29A0.0314 (13)0.0397 (15)0.0244 (13)0.0017 (11)0.0027 (10)0.0034 (11)
C30A0.100 (3)0.059 (2)0.0336 (18)0.002 (2)0.0231 (19)0.0047 (16)
C31A0.118 (4)0.050 (2)0.0384 (19)0.027 (2)0.010 (2)0.0114 (16)
C32A0.043 (2)0.186 (6)0.080 (3)0.002 (3)0.015 (2)0.091 (4)
C33A0.0287 (14)0.058 (2)0.0373 (16)0.0015 (13)0.0019 (12)0.0110 (14)
C34A0.0410 (15)0.0317 (14)0.0231 (13)0.0026 (11)0.0053 (11)0.0034 (11)
C35A0.103 (5)0.029 (2)0.036 (3)0.013 (3)0.024 (3)0.013 (2)
C36A0.040 (3)0.070 (4)0.030 (3)0.007 (2)0.000 (2)0.003 (2)
C37A0.047 (3)0.051 (3)0.027 (2)0.005 (2)0.010 (2)0.010 (2)
C38A0.0329 (14)0.0375 (15)0.0268 (13)0.0005 (11)0.0067 (11)0.0014 (11)
C39A0.0415 (15)0.0344 (14)0.0276 (14)0.0011 (12)0.0051 (12)0.0044 (11)
C40A0.132 (4)0.083 (3)0.034 (2)0.039 (3)0.016 (2)0.0137 (19)
C41A0.053 (3)0.273 (9)0.076 (3)0.041 (4)0.001 (2)0.099 (5)
C42A0.275 (8)0.048 (2)0.042 (2)0.037 (4)0.002 (3)0.0184 (19)
C43A0.0440 (16)0.0374 (15)0.0316 (15)0.0091 (12)0.0081 (12)0.0068 (12)
C44A0.0352 (14)0.0373 (15)0.0252 (13)0.0001 (11)0.0036 (11)0.0083 (11)
C45A0.073 (2)0.0421 (18)0.0461 (19)0.0083 (16)0.0024 (17)0.0118 (15)
C46A0.064 (2)0.068 (2)0.0268 (15)0.0078 (18)0.0095 (15)0.0088 (15)
C47A0.0448 (19)0.100 (3)0.0395 (19)0.0093 (19)0.0080 (15)0.0306 (19)
C48A0.0400 (15)0.0280 (14)0.0392 (16)0.0048 (11)0.0074 (12)0.0035 (12)
C35C0.043 (5)0.041 (5)0.031 (4)0.004 (4)0.002 (3)0.018 (3)
C36C0.041 (4)0.047 (5)0.026 (4)0.003 (4)0.006 (3)0.011 (3)
C37C0.085 (8)0.042 (5)0.029 (4)0.007 (5)0.004 (4)0.004 (4)
C1G0.091 (3)0.092 (3)0.056 (3)0.009 (3)0.020 (2)0.014 (2)
Cl1G0.1413 (12)0.0810 (8)0.0632 (7)0.0040 (8)0.0196 (7)0.0072 (6)
Cl2G0.1168 (11)0.1275 (12)0.1013 (11)0.0235 (9)0.0327 (9)0.0333 (9)
Geometric parameters (Å, º) top
O1—C11.390 (3)O2A—C8A1.382 (3)
O1—C331.428 (3)O2A—C38A1.432 (3)
O2—C81.376 (3)O3A—C15A1.390 (3)
O2—C381.428 (3)O3A—C43A1.435 (3)
O3—C151.390 (3)O4A—C22A1.392 (3)
O3—C431.418 (3)O4A—C48A1.425 (3)
O4—C221.392 (3)C1A—C6A1.396 (3)
O4—C481.433 (3)C1A—C2A1.397 (3)
C1—C61.389 (3)C2A—C3A1.391 (3)
C1—C21.397 (3)C2A—C28A1.519 (3)
C2—C31.396 (4)C3A—C4A1.400 (3)
C2—C281.523 (3)C3A—H3A0.9500
C3—C41.397 (4)C4A—C5A1.397 (4)
C3—H30.9500C4A—C29A1.542 (3)
C4—C51.390 (4)C5A—C6A1.389 (3)
C4—C291.538 (4)C5A—H5A0.9500
C5—C61.391 (4)C6A—C7A1.520 (3)
C5—H50.9500C7A—C9A1.521 (3)
C6—C71.520 (4)C7A—H7A10.9900
C7—C91.517 (4)C7A—H7A20.9900
C7—H7A0.9900C8A—C9A1.398 (3)
C7—H7B0.9900C8A—C13A1.403 (3)
C8—C131.398 (3)C9A—C10A1.395 (3)
C8—C91.400 (4)C10A—C11A1.392 (4)
C9—C101.387 (4)C10A—H10A0.9500
C10—C111.407 (4)C11A—C12A1.394 (4)
C10—H100.9500C11A—C34A1.539 (3)
C11—C121.386 (4)C12A—C13A1.391 (3)
C11—C341.529 (4)C12A—H12A0.9500
C12—C131.398 (3)C13A—C14A1.515 (3)
C12—H120.9500C14A—C16A1.523 (3)
C13—C141.515 (4)C14A—H14A0.9900
C14—C161.527 (3)C14A—H14B0.9900
C14—H14C0.9900C15A—C16A1.388 (3)
C14—H14D0.9900C15A—C20A1.402 (3)
C15—C161.395 (3)C16A—C17A1.404 (3)
C15—C201.396 (3)C17A—C18A1.386 (3)
C16—C171.391 (4)C17A—H17A0.9500
C17—C181.396 (4)C18A—C19A1.398 (3)
C17—H170.9500C18A—C39A1.535 (4)
C18—C191.392 (4)C19A—C20A1.393 (3)
C18—C391.532 (4)C19A—H19A0.9500
C19—C201.387 (4)C20A—C21A1.516 (3)
C19—H190.9500C21A—C23A1.517 (3)
C20—C211.520 (3)C21A—H21A0.9900
C21—C231.517 (4)C21A—H21B0.9900
C21—H21C0.9900C22A—C27A1.397 (3)
C21—H21D0.9900C22A—C23A1.402 (3)
C22—C271.393 (4)C23A—C24A1.383 (3)
C22—C231.394 (3)C24A—C25A1.397 (4)
C23—C241.391 (4)C24A—H24A0.9500
C24—C251.404 (4)C25A—C26A1.397 (3)
C24—H240.9500C25A—C44A1.535 (3)
C25—C261.395 (4)C26A—C27A1.391 (3)
C25—C441.532 (4)C26A—H26A0.9500
C26—C271.391 (3)C27A—C28A1.524 (3)
C26—H260.9500C28A—H28A0.9900
C27—C281.517 (3)C28A—H28B0.9900
C28—H28C0.9900C29A—C31A1.513 (5)
C28—H28D0.9900C29A—C30A1.518 (4)
C29—C321.495 (5)C29A—C32A1.527 (5)
C29—C301.505 (5)C30A—H30D0.9800
C29—C311.569 (6)C30A—H30E0.9800
C30—H30A0.9800C30A—H30F0.9800
C30—H30B0.9800C31A—H31D0.9800
C30—H30C0.9800C31A—H31E0.9800
C31—H31A0.9800C31A—H31F0.9800
C31—H31B0.9800C32A—H32D0.9800
C31—H31C0.9800C32A—H32E0.9800
C32—H32A0.9800C32A—H32F0.9800
C32—H32B0.9800C33A—H33D0.9800
C32—H32C0.9800C33A—H33E0.9800
C33—H33A0.9800C33A—H33F0.9800
C33—H33B0.9800C34A—C37C1.439 (9)
C33—H33C0.9800C34A—C35A1.476 (5)
C34—C361.534 (5)C34A—C35C1.520 (8)
C34—C351.536 (5)C34A—C36A1.525 (5)
C34—C371.544 (5)C34A—C37A1.588 (5)
C35—H35A0.9800C34A—C36C1.667 (8)
C35—H35B0.9800C35A—H35D0.9800
C35—H35C0.9800C35A—H35E0.9800
C36—H36A0.9800C35A—H35F0.9800
C36—H36B0.9800C36A—H36D0.9800
C36—H36C0.9800C36A—H36E0.9800
C37—H37A0.9800C36A—H36F0.9800
C37—H37B0.9800C37A—H37D0.9800
C37—H37C0.9800C37A—H37E0.9800
C38—H38D0.9800C37A—H37F0.9800
C38—H38E0.9800C38A—H38A0.9800
C38—H38F0.9800C38A—H38B0.9800
C39—C421.488 (6)C38A—H38C0.9800
C39—C401.506 (6)C39A—C41A1.504 (5)
C39—C411.534 (6)C39A—C40A1.505 (5)
C40—H40A0.9800C39A—C42A1.509 (5)
C40—H40B0.9800C40A—H40D0.9800
C40—H40C0.9800C40A—H40E0.9800
C41—H41A0.9800C40A—H40F0.9800
C41—H41B0.9800C41A—H41D0.9800
C41—H41C0.9800C41A—H41E0.9800
C42—H42A0.9800C41A—H41F0.9800
C42—H42B0.9800C42A—H42D0.9800
C42—H42C0.9800C42A—H42E0.9800
C43—H43A0.9800C42A—H42F0.9800
C43—H43B0.9800C43A—H43D0.9800
C43—H43C0.9800C43A—H43E0.9800
C44—C46B1.494 (7)C43A—H43F0.9800
C44—C47B1.499 (7)C44A—C47A1.522 (4)
C44—C471.503 (11)C44A—C45A1.535 (4)
C44—C451.520 (11)C44A—C46A1.536 (4)
C44—C45B1.573 (7)C45A—H45G0.9800
C44—C461.592 (12)C45A—H45H0.9800
C45B—H45D0.9800C45A—H45I0.9800
C45B—H45E0.9800C46A—H46G0.9800
C45B—H45F0.9800C46A—H46H0.9800
C46B—H46D0.9800C46A—H46I0.9800
C46B—H46E0.9800C47A—H47G0.9800
C46B—H46F0.9800C47A—H47H0.9800
C47B—H47D0.9800C47A—H47I0.9800
C47B—H47E0.9800C48A—H48D0.9800
C47B—H47F0.9800C48A—H48E0.9800
C48—H48A0.9800C48A—H48F0.9800
C48—H48B0.9800C35C—H35G0.9800
C48—H48C0.9800C35C—H35H0.9800
C45—H45A0.9800C35C—H35I0.9800
C45—H45B0.9800C36C—H36G0.9800
C45—H45C0.9800C36C—H36H0.9800
C46—H46A0.9800C36C—H36I0.9800
C46—H46B0.9800C37C—H37G0.9800
C46—H46C0.9800C37C—H37H0.9800
C47—H47A0.9800C37C—H37I0.9800
C47—H47B0.9800C1G—Cl1G1.732 (5)
C47—H47C0.9800C1G—Cl2G1.762 (5)
O1A—C1A1.386 (3)C1G—H1G10.9900
O1A—C33A1.433 (3)C1G—H1G20.9900
C1—O1—C33114.18 (18)H47B—C47—H47C109.5
C8—O2—C38115.73 (19)C1A—O1A—C33A113.35 (19)
C15—O3—C43113.77 (19)C8A—O2A—C38A115.31 (18)
C22—O4—C48113.5 (2)C15A—O3A—C43A114.37 (19)
C6—C1—O1120.0 (2)C22A—O4A—C48A115.01 (19)
C6—C1—C2120.9 (2)O1A—C1A—C6A119.9 (2)
O1—C1—C2119.1 (2)O1A—C1A—C2A119.4 (2)
C3—C2—C1118.6 (2)C6A—C1A—C2A120.6 (2)
C3—C2—C28119.6 (2)C3A—C2A—C1A119.0 (2)
C1—C2—C28121.7 (2)C3A—C2A—C28A120.4 (2)
C2—C3—C4121.9 (2)C1A—C2A—C28A120.5 (2)
C2—C3—H3119.0C2A—C3A—C4A121.8 (2)
C4—C3—H3119.0C2A—C3A—H3A119.1
C5—C4—C3117.3 (2)C4A—C3A—H3A119.1
C5—C4—C29120.7 (2)C5A—C4A—C3A117.4 (2)
C3—C4—C29122.0 (2)C5A—C4A—C29A120.9 (2)
C4—C5—C6122.5 (2)C3A—C4A—C29A121.7 (2)
C4—C5—H5118.7C6A—C5A—C4A122.3 (2)
C6—C5—H5118.7C6A—C5A—H5A118.8
C1—C6—C5118.6 (2)C4A—C5A—H5A118.8
C1—C6—C7121.4 (2)C5A—C6A—C1A118.7 (2)
C5—C6—C7119.9 (2)C5A—C6A—C7A120.3 (2)
C9—C7—C6110.1 (2)C1A—C6A—C7A121.0 (2)
C9—C7—H7A109.6C6A—C7A—C9A112.4 (2)
C6—C7—H7A109.6C6A—C7A—H7A1109.1
C9—C7—H7B109.6C9A—C7A—H7A1109.1
C6—C7—H7B109.6C6A—C7A—H7A2109.1
H7A—C7—H7B108.2C9A—C7A—H7A2109.1
O2—C8—C13119.4 (2)H7A1—C7A—H7A2107.9
O2—C8—C9119.4 (2)O2A—C8A—C9A119.6 (2)
C13—C8—C9121.0 (2)O2A—C8A—C13A119.1 (2)
C10—C9—C8118.4 (2)C9A—C8A—C13A121.1 (2)
C10—C9—C7121.5 (2)C10A—C9A—C8A118.3 (2)
C8—C9—C7119.9 (2)C10A—C9A—C7A121.2 (2)
C9—C10—C11122.5 (2)C8A—C9A—C7A120.4 (2)
C9—C10—H10118.8C11A—C10A—C9A122.5 (2)
C11—C10—H10118.8C11A—C10A—H10A118.8
C12—C11—C10117.2 (2)C9A—C10A—H10A118.8
C12—C11—C34123.2 (2)C10A—C11A—C12A117.4 (2)
C10—C11—C34119.5 (2)C10A—C11A—C34A121.8 (2)
C11—C12—C13122.4 (2)C12A—C11A—C34A120.8 (2)
C11—C12—H12118.8C13A—C12A—C11A122.6 (2)
C13—C12—H12118.8C13A—C12A—H12A118.7
C8—C13—C12118.6 (2)C11A—C12A—H12A118.7
C8—C13—C14120.2 (2)C12A—C13A—C8A118.2 (2)
C12—C13—C14121.3 (2)C12A—C13A—C14A121.6 (2)
C13—C14—C16111.7 (2)C8A—C13A—C14A120.0 (2)
C13—C14—H14C109.3C13A—C14A—C16A111.04 (19)
C16—C14—H14C109.3C13A—C14A—H14A109.4
C13—C14—H14D109.3C16A—C14A—H14A109.4
C16—C14—H14D109.3C13A—C14A—H14B109.4
H14C—C14—H14D107.9C16A—C14A—H14B109.4
O3—C15—C16120.0 (2)H14A—C14A—H14B108.0
O3—C15—C20119.4 (2)C16A—C15A—O3A119.8 (2)
C16—C15—C20120.5 (2)C16A—C15A—C20A120.7 (2)
C17—C16—C15119.1 (2)O3A—C15A—C20A119.2 (2)
C17—C16—C14119.7 (2)C15A—C16A—C17A118.8 (2)
C15—C16—C14121.1 (2)C15A—C16A—C14A121.8 (2)
C16—C17—C18121.8 (2)C17A—C16A—C14A119.1 (2)
C16—C17—H17119.1C18A—C17A—C16A122.2 (2)
C18—C17—H17119.1C18A—C17A—H17A118.9
C19—C18—C17117.3 (2)C16A—C17A—H17A118.9
C19—C18—C39121.3 (2)C17A—C18A—C19A117.2 (2)
C17—C18—C39121.5 (2)C17A—C18A—C39A122.3 (2)
C20—C19—C18122.6 (2)C19A—C18A—C39A120.5 (2)
C20—C19—H19118.7C20A—C19A—C18A122.6 (2)
C18—C19—H19118.7C20A—C19A—H19A118.7
C19—C20—C15118.6 (2)C18A—C19A—H19A118.7
C19—C20—C21120.9 (2)C19A—C20A—C15A118.3 (2)
C15—C20—C21120.3 (2)C19A—C20A—C21A120.4 (2)
C23—C21—C20113.2 (2)C15A—C20A—C21A121.2 (2)
C23—C21—H21C108.9C20A—C21A—C23A113.02 (19)
C20—C21—H21C108.9C20A—C21A—H21A109.0
C23—C21—H21D108.9C23A—C21A—H21A109.0
C20—C21—H21D108.9C20A—C21A—H21B109.0
H21C—C21—H21D107.7C23A—C21A—H21B109.0
O4—C22—C27119.0 (2)H21A—C21A—H21B107.8
O4—C22—C23119.3 (2)O4A—C22A—C27A120.0 (2)
C27—C22—C23121.6 (2)O4A—C22A—C23A119.0 (2)
C24—C23—C22118.3 (2)C27A—C22A—C23A120.9 (2)
C24—C23—C21120.5 (2)C24A—C23A—C22A118.4 (2)
C22—C23—C21121.1 (2)C24A—C23A—C21A121.2 (2)
C23—C24—C25122.3 (2)C22A—C23A—C21A120.4 (2)
C23—C24—H24118.8C23A—C24A—C25A122.8 (2)
C25—C24—H24118.8C23A—C24A—H24A118.6
C26—C25—C24117.0 (2)C25A—C24A—H24A118.6
C26—C25—C44121.1 (2)C26A—C25A—C24A117.1 (2)
C24—C25—C44121.9 (2)C26A—C25A—C44A122.6 (2)
C27—C26—C25122.6 (2)C24A—C25A—C44A120.3 (2)
C27—C26—H26118.7C27A—C26A—C25A122.2 (2)
C25—C26—H26118.7C27A—C26A—H26A118.9
C26—C27—C22118.2 (2)C25A—C26A—H26A118.9
C26—C27—C28120.6 (2)C26A—C27A—C22A118.6 (2)
C22—C27—C28121.1 (2)C26A—C27A—C28A120.6 (2)
C27—C28—C2113.43 (19)C22A—C27A—C28A120.7 (2)
C27—C28—H28C108.9C2A—C28A—C27A113.01 (19)
C2—C28—H28C108.9C2A—C28A—H28A109.0
C27—C28—H28D108.9C27A—C28A—H28A109.0
C2—C28—H28D108.9C2A—C28A—H28B109.0
H28C—C28—H28D107.7C27A—C28A—H28B109.0
C32—C29—C30112.5 (4)H28A—C28A—H28B107.8
C32—C29—C4111.7 (3)C31A—C29A—C30A107.1 (3)
C30—C29—C4112.7 (3)C31A—C29A—C32A109.0 (4)
C32—C29—C31105.4 (4)C30A—C29A—C32A108.6 (3)
C30—C29—C31106.8 (4)C31A—C29A—C4A112.7 (2)
C4—C29—C31107.2 (3)C30A—C29A—C4A111.1 (2)
C29—C30—H30A109.5C32A—C29A—C4A108.3 (2)
C29—C30—H30B109.5C29A—C30A—H30D109.5
H30A—C30—H30B109.5C29A—C30A—H30E109.5
C29—C30—H30C109.5H30D—C30A—H30E109.5
H30A—C30—H30C109.5C29A—C30A—H30F109.5
H30B—C30—H30C109.5H30D—C30A—H30F109.5
C29—C31—H31A109.5H30E—C30A—H30F109.5
C29—C31—H31B109.5C29A—C31A—H31D109.5
H31A—C31—H31B109.5C29A—C31A—H31E109.5
C29—C31—H31C109.5H31D—C31A—H31E109.5
H31A—C31—H31C109.5C29A—C31A—H31F109.5
H31B—C31—H31C109.5H31D—C31A—H31F109.5
C29—C32—H32A109.5H31E—C31A—H31F109.5
C29—C32—H32B109.5C29A—C32A—H32D109.5
H32A—C32—H32B109.5C29A—C32A—H32E109.5
C29—C32—H32C109.5H32D—C32A—H32E109.5
H32A—C32—H32C109.5C29A—C32A—H32F109.5
H32B—C32—H32C109.5H32D—C32A—H32F109.5
O1—C33—H33A109.5H32E—C32A—H32F109.5
O1—C33—H33B109.5O1A—C33A—H33D109.5
H33A—C33—H33B109.5O1A—C33A—H33E109.5
O1—C33—H33C109.5H33D—C33A—H33E109.5
H33A—C33—H33C109.5O1A—C33A—H33F109.5
H33B—C33—H33C109.5H33D—C33A—H33F109.5
C11—C34—C36109.7 (3)H33E—C33A—H33F109.5
C11—C34—C35109.2 (2)C37C—C34A—C35A138.4 (5)
C36—C34—C35110.2 (3)C37C—C34A—C35C115.6 (6)
C11—C34—C37112.3 (3)C35A—C34A—C35C48.3 (4)
C36—C34—C37108.5 (3)C37C—C34A—C36A52.3 (5)
C35—C34—C37107.0 (3)C35A—C34A—C36A113.3 (4)
C34—C35—H35A109.5C35C—C34A—C36A143.0 (4)
C34—C35—H35B109.5C37C—C34A—C11A111.1 (4)
H35A—C35—H35B109.5C35A—C34A—C11A110.6 (3)
C34—C35—H35C109.5C35C—C34A—C11A109.1 (3)
H35A—C35—H35C109.5C36A—C34A—C11A107.7 (3)
H35B—C35—H35C109.5C37C—C34A—C37A56.3 (5)
C34—C36—H36A109.5C35A—C34A—C37A107.3 (4)
C34—C36—H36B109.5C35C—C34A—C37A63.1 (4)
H36A—C36—H36B109.5C36A—C34A—C37A106.5 (3)
C34—C36—H36C109.5C11A—C34A—C37A111.5 (3)
H36A—C36—H36C109.5C37C—C34A—C36C106.3 (5)
H36B—C36—H36C109.5C35A—C34A—C36C56.8 (4)
C34—C37—H37A109.5C35C—C34A—C36C102.6 (5)
C34—C37—H37B109.5C36A—C34A—C36C59.0 (4)
H37A—C37—H37B109.5C11A—C34A—C36C111.9 (3)
C34—C37—H37C109.5C37A—C34A—C36C136.7 (4)
H37A—C37—H37C109.5C34A—C35A—H35D109.5
H37B—C37—H37C109.5C34A—C35A—H35E109.5
O2—C38—H38D109.5C34A—C35A—H35F109.5
O2—C38—H38E109.5C34A—C36A—H36D109.5
H38D—C38—H38E109.5C34A—C36A—H36E109.5
O2—C38—H38F109.5C34A—C36A—H36F109.5
H38D—C38—H38F109.5C34A—C37A—H37D109.5
H38E—C38—H38F109.5C34A—C37A—H37E109.5
C42—C39—C40112.0 (5)C34A—C37A—H37F109.5
C42—C39—C18110.8 (3)O2A—C38A—H38A109.5
C40—C39—C18112.3 (3)O2A—C38A—H38B109.5
C42—C39—C41104.2 (6)H38A—C38A—H38B109.5
C40—C39—C41109.1 (4)O2A—C38A—H38C109.5
C18—C39—C41108.0 (3)H38A—C38A—H38C109.5
C39—C40—H40A109.5H38B—C38A—H38C109.5
C39—C40—H40B109.5C41A—C39A—C40A110.0 (4)
H40A—C40—H40B109.5C41A—C39A—C42A107.0 (5)
C39—C40—H40C109.5C40A—C39A—C42A107.8 (4)
H40A—C40—H40C109.5C41A—C39A—C18A109.6 (3)
H40B—C40—H40C109.5C40A—C39A—C18A112.0 (3)
C39—C41—H41A109.5C42A—C39A—C18A110.3 (3)
C39—C41—H41B109.5C39A—C40A—H40D109.5
H41A—C41—H41B109.5C39A—C40A—H40E109.5
C39—C41—H41C109.5H40D—C40A—H40E109.5
H41A—C41—H41C109.5C39A—C40A—H40F109.5
H41B—C41—H41C109.5H40D—C40A—H40F109.5
C39—C42—H42A109.5H40E—C40A—H40F109.5
C39—C42—H42B109.5C39A—C41A—H41D109.5
H42A—C42—H42B109.5C39A—C41A—H41E109.5
C39—C42—H42C109.5H41D—C41A—H41E109.5
H42A—C42—H42C109.5C39A—C41A—H41F109.5
H42B—C42—H42C109.5H41D—C41A—H41F109.5
O3—C43—H43A109.5H41E—C41A—H41F109.5
O3—C43—H43B109.5C39A—C42A—H42D109.5
H43A—C43—H43B109.5C39A—C42A—H42E109.5
O3—C43—H43C109.5H42D—C42A—H42E109.5
H43A—C43—H43C109.5C39A—C42A—H42F109.5
H43B—C43—H43C109.5H42D—C42A—H42F109.5
C46B—C44—C47B110.4 (5)H42E—C42A—H42F109.5
C46B—C44—C47141.9 (5)O3A—C43A—H43D109.5
C47B—C44—C4744.2 (6)O3A—C43A—H43E109.5
C46B—C44—C4557.4 (7)H43D—C43A—H43E109.5
C47B—C44—C45131.4 (5)O3A—C43A—H43F109.5
C47—C44—C45113.3 (9)H43D—C43A—H43F109.5
C46B—C44—C25107.5 (3)H43E—C43A—H43F109.5
C47B—C44—C25113.5 (3)C47A—C44A—C25A112.6 (2)
C47—C44—C25109.2 (4)C47A—C44A—C45A108.9 (3)
C45—C44—C25114.9 (4)C25A—C44A—C45A108.7 (2)
C46B—C44—C45B108.1 (5)C47A—C44A—C46A108.2 (3)
C47B—C44—C45B108.3 (6)C25A—C44A—C46A110.1 (2)
C47—C44—C45B68.6 (7)C45A—C44A—C46A108.2 (3)
C45—C44—C45B51.3 (6)C44A—C45A—H45G109.5
C25—C44—C45B108.9 (3)C44A—C45A—H45H109.5
C46B—C44—C4649.5 (5)H45G—C45A—H45H109.5
C47B—C44—C4665.7 (7)C44A—C45A—H45I109.5
C47—C44—C46108.9 (8)H45G—C45A—H45I109.5
C45—C44—C46102.9 (8)H45H—C45A—H45I109.5
C25—C44—C46107.2 (5)C44A—C46A—H46G109.5
C45B—C44—C46142.3 (5)C44A—C46A—H46H109.5
C44—C45B—H45D109.5H46G—C46A—H46H109.5
C44—C45B—H45E109.5C44A—C46A—H46I109.5
C44—C45B—H45F109.5H46G—C46A—H46I109.5
C44—C46B—H46D109.5H46H—C46A—H46I109.5
C44—C46B—H46E109.5C44A—C47A—H47G109.5
C44—C46B—H46F109.5C44A—C47A—H47H109.5
C44—C47B—H47D109.5H47G—C47A—H47H109.5
C44—C47B—H47E109.5C44A—C47A—H47I109.5
C44—C47B—H47F109.5H47G—C47A—H47I109.5
O4—C48—H48A109.5H47H—C47A—H47I109.5
O4—C48—H48B109.5O4A—C48A—H48D109.5
H48A—C48—H48B109.5O4A—C48A—H48E109.5
O4—C48—H48C109.5H48D—C48A—H48E109.5
H48A—C48—H48C109.5O4A—C48A—H48F109.5
H48B—C48—H48C109.5H48D—C48A—H48F109.5
C44—C45—H45A109.5H48E—C48A—H48F109.5
C44—C45—H45B109.5C34A—C35C—H35G109.5
H45A—C45—H45B109.5C34A—C35C—H35H109.5
C44—C45—H45C109.5C34A—C35C—H35I109.5
H45A—C45—H45C109.5C34A—C36C—H36G109.5
H45B—C45—H45C109.5C34A—C36C—H36H109.5
C44—C46—H46A109.5C34A—C36C—H36I109.5
C44—C46—H46B109.5C34A—C37C—H37G109.5
H46A—C46—H46B109.5C34A—C37C—H37H109.5
C44—C46—H46C109.5C34A—C37C—H37I109.5
H46A—C46—H46C109.5Cl1G—C1G—Cl2G112.1 (2)
H46B—C46—H46C109.5Cl1G—C1G—H1G1109.2
C44—C47—H47A109.5Cl2G—C1G—H1G1109.2
C44—C47—H47B109.5Cl1G—C1G—H1G2109.2
H47A—C47—H47B109.5Cl2G—C1G—H1G2109.2
C44—C47—H47C109.5H1G1—C1G—H1G2107.9
H47A—C47—H47C109.5
C33—O1—C1—C694.5 (3)C33A—O1A—C1A—C6A98.2 (3)
C33—O1—C1—C289.2 (3)C33A—O1A—C1A—C2A84.6 (3)
C6—C1—C2—C32.9 (3)O1A—C1A—C2A—C3A178.6 (2)
O1—C1—C2—C3179.2 (2)C6A—C1A—C2A—C3A4.1 (3)
C6—C1—C2—C28174.1 (2)O1A—C1A—C2A—C28A4.3 (3)
O1—C1—C2—C282.2 (3)C6A—C1A—C2A—C28A172.9 (2)
C1—C2—C3—C40.3 (4)C1A—C2A—C3A—C4A2.2 (3)
C28—C2—C3—C4177.4 (2)C28A—C2A—C3A—C4A174.8 (2)
C2—C3—C4—C52.3 (4)C2A—C3A—C4A—C5A0.5 (3)
C2—C3—C4—C29177.4 (3)C2A—C3A—C4A—C29A177.5 (2)
C3—C4—C5—C61.2 (4)C3A—C4A—C5A—C6A1.4 (3)
C29—C4—C5—C6178.6 (3)C29A—C4A—C5A—C6A176.7 (2)
O1—C1—C6—C5179.8 (2)C4A—C5A—C6A—C1A0.5 (3)
C2—C1—C6—C54.0 (3)C4A—C5A—C6A—C7A177.8 (2)
O1—C1—C6—C74.3 (3)O1A—C1A—C6A—C5A179.5 (2)
C2—C1—C6—C7172.0 (2)C2A—C1A—C6A—C5A3.3 (3)
C4—C5—C6—C11.9 (4)O1A—C1A—C6A—C7A2.2 (3)
C4—C5—C6—C7174.1 (2)C2A—C1A—C6A—C7A175.0 (2)
C1—C6—C7—C9113.2 (3)C5A—C6A—C7A—C9A66.0 (3)
C5—C6—C7—C962.7 (3)C1A—C6A—C7A—C9A112.3 (2)
C38—O2—C8—C1395.4 (3)C38A—O2A—C8A—C9A93.6 (3)
C38—O2—C8—C989.5 (3)C38A—O2A—C8A—C13A91.3 (3)
O2—C8—C9—C10175.6 (2)O2A—C8A—C9A—C10A175.4 (2)
C13—C8—C9—C100.7 (4)C13A—C8A—C9A—C10A0.4 (3)
O2—C8—C9—C70.8 (3)O2A—C8A—C9A—C7A1.9 (3)
C13—C8—C9—C7174.2 (2)C13A—C8A—C9A—C7A176.9 (2)
C6—C7—C9—C10106.5 (3)C6A—C7A—C9A—C10A110.0 (3)
C6—C7—C9—C868.2 (3)C6A—C7A—C9A—C8A67.2 (3)
C8—C9—C10—C111.7 (4)C8A—C9A—C10A—C11A1.0 (4)
C7—C9—C10—C11173.1 (2)C7A—C9A—C10A—C11A176.2 (2)
C9—C10—C11—C121.8 (4)C9A—C10A—C11A—C12A1.1 (4)
C9—C10—C11—C34177.0 (2)C9A—C10A—C11A—C34A177.6 (2)
C10—C11—C12—C130.9 (4)C10A—C11A—C12A—C13A0.6 (4)
C34—C11—C12—C13177.8 (2)C34A—C11A—C12A—C13A178.1 (2)
O2—C8—C13—C12174.8 (2)C11A—C12A—C13A—C8A0.0 (3)
C9—C8—C13—C120.2 (3)C11A—C12A—C13A—C14A175.7 (2)
O2—C8—C13—C144.4 (3)O2A—C8A—C13A—C12A174.9 (2)
C9—C8—C13—C14179.4 (2)C9A—C8A—C13A—C12A0.1 (3)
C11—C12—C13—C80.0 (4)O2A—C8A—C13A—C14A0.9 (3)
C11—C12—C13—C14179.2 (2)C9A—C8A—C13A—C14A175.9 (2)
C8—C13—C14—C1670.2 (3)C12A—C13A—C14A—C16A109.1 (2)
C12—C13—C14—C16109.0 (3)C8A—C13A—C14A—C16A66.5 (3)
C43—O3—C15—C1690.7 (3)C43A—O3A—C15A—C16A102.0 (3)
C43—O3—C15—C2092.6 (3)C43A—O3A—C15A—C20A83.2 (3)
O3—C15—C16—C17179.2 (2)O3A—C15A—C16A—C17A178.2 (2)
C20—C15—C16—C172.5 (3)C20A—C15A—C16A—C17A3.5 (3)
O3—C15—C16—C141.9 (3)O3A—C15A—C16A—C14A3.6 (3)
C20—C15—C16—C14174.8 (2)C20A—C15A—C16A—C14A171.1 (2)
C13—C14—C16—C1765.4 (3)C13A—C14A—C16A—C15A114.8 (2)
C13—C14—C16—C15112.0 (3)C13A—C14A—C16A—C17A59.7 (3)
C15—C16—C17—C180.1 (4)C15A—C16A—C17A—C18A1.3 (3)
C14—C16—C17—C18177.5 (2)C14A—C16A—C17A—C18A173.4 (2)
C16—C17—C18—C191.6 (4)C16A—C17A—C18A—C19A0.6 (3)
C16—C17—C18—C39179.3 (2)C16A—C17A—C18A—C39A179.2 (2)
C17—C18—C19—C200.6 (4)C17A—C18A—C19A—C20A0.3 (3)
C39—C18—C19—C20179.6 (2)C39A—C18A—C19A—C20A178.9 (2)
C18—C19—C20—C152.0 (4)C18A—C19A—C20A—C15A1.9 (3)
C18—C19—C20—C21174.7 (2)C18A—C19A—C20A—C21A173.6 (2)
O3—C15—C20—C19179.8 (2)C16A—C15A—C20A—C19A3.8 (3)
C16—C15—C20—C193.5 (3)O3A—C15A—C20A—C19A178.47 (19)
O3—C15—C20—C213.6 (3)C16A—C15A—C20A—C21A171.6 (2)
C16—C15—C20—C21173.2 (2)O3A—C15A—C20A—C21A3.1 (3)
C19—C20—C21—C23116.1 (3)C19A—C20A—C21A—C23A114.0 (2)
C15—C20—C21—C2360.4 (3)C15A—C20A—C21A—C23A61.3 (3)
C48—O4—C22—C2795.8 (3)C48A—O4A—C22A—C27A87.2 (3)
C48—O4—C22—C2387.3 (3)C48A—O4A—C22A—C23A96.8 (2)
O4—C22—C23—C24178.9 (2)O4A—C22A—C23A—C24A177.34 (19)
C27—C22—C23—C242.1 (3)C27A—C22A—C23A—C24A1.4 (3)
O4—C22—C23—C211.9 (3)O4A—C22A—C23A—C21A1.0 (3)
C27—C22—C23—C21174.9 (2)C27A—C22A—C23A—C21A177.0 (2)
C20—C21—C23—C24115.1 (3)C20A—C21A—C23A—C24A113.6 (2)
C20—C21—C23—C2261.7 (3)C20A—C21A—C23A—C22A64.7 (3)
C22—C23—C24—C250.5 (4)C22A—C23A—C24A—C25A1.4 (3)
C21—C23—C24—C25176.4 (2)C21A—C23A—C24A—C25A177.0 (2)
C23—C24—C25—C261.0 (4)C23A—C24A—C25A—C26A1.2 (4)
C23—C24—C25—C44179.0 (2)C23A—C24A—C25A—C44A176.9 (2)
C24—C25—C26—C271.2 (4)C24A—C25A—C26A—C27A0.9 (4)
C44—C25—C26—C27179.2 (2)C44A—C25A—C26A—C27A177.1 (2)
C25—C26—C27—C220.2 (4)C25A—C26A—C27A—C22A0.9 (4)
C25—C26—C27—C28176.3 (2)C25A—C26A—C27A—C28A176.8 (2)
O4—C22—C27—C26178.8 (2)O4A—C22A—C27A—C26A177.1 (2)
C23—C22—C27—C261.9 (3)C23A—C22A—C27A—C26A1.1 (3)
O4—C22—C27—C282.2 (3)O4A—C22A—C27A—C28A0.6 (3)
C23—C22—C27—C28174.6 (2)C23A—C22A—C27A—C28A176.5 (2)
C26—C27—C28—C2109.2 (3)C3A—C2A—C28A—C27A118.3 (2)
C22—C27—C28—C267.3 (3)C1A—C2A—C28A—C27A58.7 (3)
C3—C2—C28—C27118.8 (3)C26A—C27A—C28A—C2A115.3 (2)
C1—C2—C28—C2758.2 (3)C22A—C27A—C28A—C2A62.4 (3)
C5—C4—C29—C3241.0 (5)C5A—C4A—C29A—C31A163.8 (3)
C3—C4—C29—C32139.2 (4)C3A—C4A—C29A—C31A18.3 (4)
C5—C4—C29—C30168.9 (4)C5A—C4A—C29A—C30A43.6 (4)
C3—C4—C29—C3011.4 (5)C3A—C4A—C29A—C30A138.4 (3)
C5—C4—C29—C3173.9 (4)C5A—C4A—C29A—C32A75.5 (4)
C3—C4—C29—C31105.8 (4)C3A—C4A—C29A—C32A102.4 (4)
C12—C11—C34—C36118.2 (3)C10A—C11A—C34A—C37C60.6 (6)
C10—C11—C34—C3663.1 (3)C12A—C11A—C34A—C37C118.1 (6)
C12—C11—C34—C35121.0 (3)C10A—C11A—C34A—C35A119.5 (4)
C10—C11—C34—C3557.7 (4)C12A—C11A—C34A—C35A61.8 (4)
C12—C11—C34—C372.5 (4)C10A—C11A—C34A—C35C68.0 (5)
C10—C11—C34—C37176.2 (3)C12A—C11A—C34A—C35C113.3 (5)
C19—C18—C39—C4236.7 (6)C10A—C11A—C34A—C36A116.2 (3)
C17—C18—C39—C42142.4 (5)C12A—C11A—C34A—C36A62.5 (4)
C19—C18—C39—C40162.8 (4)C10A—C11A—C34A—C37A0.3 (4)
C17—C18—C39—C4016.3 (5)C12A—C11A—C34A—C37A178.9 (3)
C19—C18—C39—C4176.9 (4)C10A—C11A—C34A—C36C179.1 (4)
C17—C18—C39—C41104.1 (4)C12A—C11A—C34A—C36C0.5 (5)
C26—C25—C44—C46B64.9 (4)C17A—C18A—C39A—C41A103.5 (4)
C24—C25—C44—C46B117.2 (4)C19A—C18A—C39A—C41A77.9 (5)
C26—C25—C44—C47B172.7 (6)C17A—C18A—C39A—C40A18.9 (4)
C24—C25—C44—C47B5.2 (7)C19A—C18A—C39A—C40A159.7 (3)
C26—C25—C44—C47125.2 (8)C17A—C18A—C39A—C42A139.0 (4)
C24—C25—C44—C4752.7 (8)C19A—C18A—C39A—C42A39.6 (5)
C26—C25—C44—C453.3 (8)C26A—C25A—C44A—C47A7.4 (4)
C24—C25—C44—C45178.8 (8)C24A—C25A—C44A—C47A174.6 (3)
C26—C25—C44—C45B52.0 (5)C26A—C25A—C44A—C45A113.3 (3)
C24—C25—C44—C45B125.9 (4)C24A—C25A—C44A—C45A64.6 (3)
C26—C25—C44—C46116.9 (6)C26A—C25A—C44A—C46A128.4 (3)
C24—C25—C44—C4665.2 (6)C24A—C25A—C44A—C46A53.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C33A—H33E···Cl1Gi0.982.923.711 (3)139
C46—H46A···Cl2Gii0.982.893.551 (10)126
C7A—H7A1···CgCi0.992.883.733 (2)145
C33—H33A···CgA'iii0.982.743.549 (3)140
C48—H48A···CgC'0.982.763.526 (3)136
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+2; (iii) x+2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC48H64O4·0.5CH2Cl2
Mr747.46
Crystal system, space groupMonoclinic, P21/c
Temperature (K)133
a, b, c (Å)16.7012 (6), 19.7113 (8), 28.2577 (11)
β (°) 103.097 (2)
V3)9060.5 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.60 × 0.60 × 0.60
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.929, 0.929
No. of measured, independent and
observed [I > 2σ(I)] reflections
186561, 20781, 12758
Rint0.051
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.272, 1.21
No. of reflections20781
No. of parameters1058
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.83, 1.13

Computer programs: APEX2 (Bruker, 2004), SAINT-NT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C33A—H33E···Cl1Gi0.982.923.711 (3)138.8
C46—H46A···Cl2Gii0.982.893.551 (10)125.8
C7A—H7A1···CgCi0.992.883.733 (2)145.2
C33—H33A···CgA'iii0.982.743.549 (3)140.3
C48—H48A···CgC'0.982.763.526 (3)135.5
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z+2; (iii) x+2, y+1/2, z+3/2.
 

Acknowledgements

Financial support from the German Federal Ministry of Economics and Technolgy (BMWi) under grant No. 16IN0218 `ChemoChips' is gratefully acknowledged.

References

First citationBitter, I., Grün, A., Ágai, B. & Tôke, L. (1995). Tetrahedron, 51, 7835–7840.  CrossRef CAS Web of Science Google Scholar
First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFischer, C., Gruber, T., Seichter, W. & Weber, E. (2007). Acta Cryst. E63, o4572–o4573.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGrootenhuis, P. D. J., Kollman, P. A., Groenen, L. C., Reinhoudt, D. N., van Hummel, G. J., Ugozzoli, F. & Andreetti, G. D. (1990). J. Am. Chem. Soc. 112, 4165–4176.  CSD CrossRef CAS Web of Science Google Scholar
First citationGutsche, C. D., Dhawan, B., Levine, J. A., No, K. H. & Bauer, L. J. (1983). Tetrahedron, 39, 409–426.  CrossRef CAS Web of Science Google Scholar
First citationIwamoto, K., Araki, K. & Shinkai, S. (1991). J. Org. Chem. 56, 4955–4962.  CrossRef CAS Web of Science Google Scholar
First citationNishio, M. (2004). CrystEngComm, 6, 130–158.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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