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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 4| April 2014| Pages o492-o493

Methyl 6-O-trityl-α-D-gluco­pyran­oside methanol disolvate

aDepartment of Chemistry, Çankırı Karatekin University, TR-18100, Çankırı, Turkey, bDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey, and cUniversität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany
*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 5 March 2014; accepted 24 March 2014; online 29 March 2014)

The asymmetric unit of the title compound, C26H28O6·2CH3OH, contains two independent methyl 6-O-trityl-α-D-gluco­pyran­oside mol­ecules and four methanol solvent mol­ecules. The rings of two methyl α-D-gluco­pyran­oside adopt chair conformations. In the crystal, extensive intra- and inter­molecular O—H⋯O and C—H⋯O hydrogen bonds link the mol­ecules into a three-dimensional supra­molecular architecture.

Related literature

For intra­molecular 1,3-dipolar cyclo­additions of various carbohydrates, see: Kobayashi et al. (1994[Kobayashi, Y., Miyazaki, H. & Shiozaki, M. (1994). J. Org. Chem. 59, 813-822.]); Kleban et al. (2001[Kleban, M., Hilgers, P., Greul, J. N., Kugler, R. D., Li, J., Picasso, S., Vogel, P. & Jäger, V. (2001). Chembiochem, pp. 365-368.]); Dransfield et al. (1999[Dransfield, P. J., Moutel, S., Shipman, M. & Sik, V. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 3349-3335.]); Gallos et al. (1999[Gallos, J. K., Koumbis, A. E., Xiraphaki, V. P., Dellios, C. C. & Coutouli-Argyropoulou, E. (1999). Tetrahedron, 55, 15167-15180.]). For the importance of the title compound for the preparation of di- and tris­accharide analogues after several steps, see: Peri et al. (2002[Peri, F., Deutman, A., Ferla, B. L. & Nicotra, F. (2002). Chem. Commun. pp. 1504-1505.], 2004[Peri, F., Jiménez-Barbero, J., Garcia-Aparicio, V., Travoška, I. & Nicotra, F. (2004). Eur. J. Chem. 10, 1433-1444.]); Lopez et al. (2011[Lopez, M., Trajkovic, J., Bornaghi, L., Innocenti, A., Vullo, D., Supuran, C. T. & Poulsen, S. A. (2011). J. Med. Chem. 54, 1481-1489.]). For the use of alkyl-5-enyl aldehydes as inter­mediates for the syntheses of bi­cyclo­[x.3.0] or bi­cyclo­[x.2.1] derivatives after 1,3-dipolar cyclo­additions, see: Dransfield et al. (1999[Dransfield, P. J., Moutel, S., Shipman, M. & Sik, V. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 3349-3335.]). For the preparation of the title compound, see: Horton & Lauterback (1969[Horton, D. & Lauterback, J. H. (1969). J. Org. Chem. pp. 86-92.]); Bernet & Vasella (1979[Bernet, B. & Vasella, A. (1979). Helv. Chim. Acta, 62, 2401-2410.]); Komiotis et al. (2006[Komiotis, D., Agelis, G., Manta, S., Tzioumaki, N. & Tsoukala, E. (2006). J. Carbohydr. Chem. 25, 441-450.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C26H28O6·2CH4O

  • Mr = 500.57

  • Triclinic, P 1

  • a = 8.6763 (4) Å

  • b = 9.1233 (4) Å

  • c = 19.1545 (6) Å

  • α = 86.328 (3)°

  • β = 82.578 (2)°

  • γ = 67.903 (2)°

  • V = 1392.87 (10) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 299 K

  • 0.44 × 0.41 × 0.22 mm

Data collection
  • Bruker Kappa APEXII DUO diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.720, Tmax = 0.745

  • 40377 measured reflections

  • 11390 independent reflections

  • 10449 reflections with I > 2σ(I)

  • Rint = 0.017

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.096

  • S = 1.07

  • 11390 reflections

  • 695 parameters

  • 8 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3A—H31⋯O10 0.84 (3) 1.88 (3) 2.707 (2) 169 (2)
O3B—H32⋯O7 0.82 (3) 1.91 (3) 2.713 (2) 165 (3)
O4A—H41⋯O2B 0.83 (3) 2.02 (2) 2.8287 (18) 164.5 (19)
O4B—H42⋯O2Ai 0.77 (3) 2.15 (3) 2.9046 (19) 166 (3)
O5A—H51⋯O8 0.79 (3) 1.87 (3) 2.667 (2) 175 (4)
O5B—H52⋯O9i 0.81 (4) 1.90 (4) 2.704 (2) 173 (3)
O7—H71⋯O5Ai 0.79 (2) 1.98 (2) 2.763 (2) 170 (3)
O8—H81⋯O3B 0.90 (3) 1.84 (3) 2.727 (2) 170 (3)
O9—H91⋯O3A 0.85 (4) 1.91 (4) 2.741 (2) 167 (4)
O10—H101⋯O5B 0.81 (3) 1.95 (3) 2.754 (2) 170 (3)
C1B—H1B⋯O3Aii 0.98 2.32 3.2469 (19) 157
C3A—H3A⋯O4Biii 0.98 2.59 3.471 (2) 149
C3B—H3B⋯O4A 0.98 2.49 3.391 (2) 153
C15B—H15B⋯O1B 0.93 2.52 3.417 (2) 161
C25A—H25A⋯O1A 0.93 2.60 3.443 (2) 151
Symmetry codes: (i) x-1, y, z; (ii) x, y-1, z; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The intramolecular 1,3-dipolar cycloadditions of various carbohydrates have been reported by several authors (Kobayashi et al., 1994; Kleban et al., 2001; Dransfield et al., 1999; Gallos et al., 1999). 1,3-Dipolar cycloadducts of various carbohdrates were converted into the amino (hydroxymethyl) cyclopentanetriols which are useful for glycosidase inhibitors (Kleban et al., 2001). The title compound is useful for the preparation of di- and trisaccharide analogues after several steps (Peri et al., 2002, 2004; Lopez et al., 2011), and it can be easily converted to the alkyl-5-enyl aldehydes. These aldehydes are useful intermediates for the syntheses of bicyclo[x.3.0] or bicyclo[x.2.1] derivatives after 1,3-dipolar cycloadditions (Dransfield et al., 1999). The present study was undertaken to ascertain the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules and four methanol solvent molecules (Fig. 1). The methyl α-D-glucopyranoside rings [A (O1a/C1a–C5a) and A' (O1b/C1b–C5b)] are in chair conformations with puckering parameters (Cremer & Pople, 1975) of QT = 0.551 (2)Å, ϕ = -5.8(2.5)°, θ = 4.4 (2)° and QT = 0.550 (2)Å, ϕ = -40.7(4.9)°, θ = 2.0 (2)°, respectively. In trityl cation, the rings B (C8a–C13a), C (C14a–C19a), D (C20a–C25a) and B' (C8b–C13b), C' (C14b–C19b), D'(C20b–C25b) are oriented at dihedral angles of A/B = 74.16 (6), A/C = 63.29 (7), B/C = 83.19 (6) ° and A'/B' = 82.73 (6), A'/C' = 73.69 (7), B'/C' = 65.34 (6) °, respectively. The intramolecular O—H···O and C—H···O hydrogen bonds (Table 1) link the molecules in the asymmetric unit.

In the crystal structure, intra- and intermolecular O-H···O and C-H···O hydrogen bonds (Table 1, Fig. 2) link the molecules into a three-dimensional structure.

Related literature top

For intramolecular 1,3-dipolar cycloadditions of various carbohydrates, see: Kobayashi et al. (1994); Kleban et al. (2001); Dransfield et al. (1999); Gallos et al. (1999). For the importance of the title compound for the preparation of di- and trisaccharide analogues after several steps, see: Peri et al. (2002, 2004); Lopez et al. (2011). For the use of alkyl-5-enyl aldehydes as intermediates for the syntheses of bicyclo[x.3.0] or bicyclo[x.2.1] derivatives after 1,3-dipolar cycloadditions, see: Dransfield et al. (1999). For the preparation of the title compound, see: Horton & Lauterback (1969); Bernet & Vasella (1979); Komiotis et al. (2006). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was synthesized by the literature method (Horton et al., 1969; Bernet & Vasella, 1979; Komiotis et al., 2006). α-D-glucopyranoside (10.0 g, 51.49 mmol) and triphenyl methyl chloride (14.4 g, 52.0 mmol) in pyridine (100 ml) was heated for 3 h at 373 K under argon atmosphere, and then the yellowish solution was stirred overnight at room temperature for 24 h. Pyridine was removed in vacuo and water (100 ml) was added to the mixture. The crude mixture was extracted with EtOAc (4 × 50 ml). Combined organic layer was dried over MgSO4, filtered and the solvent was removed in vacuo. Crystallization of the crude product in MeOH:petroleum ether (5:1) gave a colorless crystalline solid (yield: 80%), m.p.: 410–411 K, literature m.p.: 421-422 K (Bernet & Vasella, 1979).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms have been omitted for clarity.
[Figure 2] Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.
Methyl 6-O-trityl-α-D-glucopyranoside methanol disolvate top
Crystal data top
C26H28O6·2CH4OZ = 2
Mr = 500.57F(000) = 536
Triclinic, P1Dx = 1.194 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6763 (4) ÅCell parameters from 10444 reflections
b = 9.1233 (4) Åθ = 2.1–26.5°
c = 19.1545 (6) ŵ = 0.09 mm1
α = 86.328 (3)°T = 299 K
β = 82.578 (2)°Block, colourless
γ = 67.903 (2)°0.44 × 0.41 × 0.22 mm
V = 1392.87 (10) Å3
Data collection top
Bruker Kappa APEXII DUO
diffractometer
11390 independent reflections
Radiation source: fine-focus sealed tube10449 reflections with I > 2σ(I)
Triumph monochromatorRint = 0.017
ω + Phi Scans scansθmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1010
Tmin = 0.720, Tmax = 0.745k = 1111
40377 measured reflectionsl = 2323
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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0559P)2 + 0.1152P]
where P = (Fo2 + 2Fc2)/3
11390 reflections(Δ/σ)max = 0.001
695 parametersΔρmax = 0.22 e Å3
8 restraintsΔρmin = 0.24 e Å3
Crystal data top
C26H28O6·2CH4Oγ = 67.903 (2)°
Mr = 500.57V = 1392.87 (10) Å3
Triclinic, P1Z = 2
a = 8.6763 (4) ÅMo Kα radiation
b = 9.1233 (4) ŵ = 0.09 mm1
c = 19.1545 (6) ÅT = 299 K
α = 86.328 (3)°0.44 × 0.41 × 0.22 mm
β = 82.578 (2)°
Data collection top
Bruker Kappa APEXII DUO
diffractometer
11390 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
10449 reflections with I > 2σ(I)
Tmin = 0.720, Tmax = 0.745Rint = 0.017
40377 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0358 restraints
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.22 e Å3
11390 reflectionsΔρmin = 0.24 e Å3
695 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.67336 (14)0.99787 (12)0.09862 (5)0.0469 (3)
O2A0.77130 (15)0.98268 (14)0.20819 (6)0.0500 (3)
O3A0.46073 (17)1.02657 (14)0.27635 (6)0.0524 (3)
H310.369 (3)1.024 (3)0.2948 (12)0.063 (6)*
O4A0.40182 (15)0.77468 (16)0.21955 (7)0.0558 (3)
H410.428 (2)0.678 (3)0.2258 (10)0.053 (5)*
O5A0.67937 (16)0.59516 (13)0.11406 (7)0.0540 (3)
H510.603 (3)0.570 (4)0.1095 (17)0.109 (11)*
O6A0.92014 (12)0.84787 (12)0.01329 (5)0.0395 (2)
C1A0.6321 (2)1.04331 (18)0.16985 (8)0.0455 (4)
H1A0.58871.15910.17150.055*
C2A0.4962 (2)0.98605 (18)0.20406 (8)0.0435 (3)
H2A0.39461.04100.18110.052*
C3A0.54653 (19)0.81009 (18)0.19520 (8)0.0426 (3)
H3A0.63590.75280.22450.051*
C4A0.60696 (19)0.76254 (17)0.11881 (8)0.0417 (3)
H4A0.51170.80320.09110.050*
C5A0.7386 (2)0.82993 (17)0.08876 (8)0.0403 (3)
H5A0.83980.78020.11250.048*
C6A0.7810 (2)0.80281 (19)0.01065 (8)0.0420 (3)
H610.80920.69210.00090.050*
H620.68540.86540.01370.050*
C7A0.95558 (17)0.85998 (17)0.08845 (7)0.0361 (3)
C8A0.97374 (18)0.70260 (18)0.11965 (7)0.0391 (3)
C9A0.8427 (2)0.6814 (2)0.14656 (9)0.0507 (4)
H9A0.74650.76870.15360.061*
C10A0.8531 (3)0.5325 (3)0.16304 (10)0.0630 (5)
H10A0.76390.52060.18100.076*
C11A0.9938 (3)0.4019 (2)0.15317 (11)0.0669 (5)
H11A0.99990.30170.16380.080*
C12A1.1259 (3)0.4207 (2)0.12731 (11)0.0631 (5)
H12A1.22220.33300.12090.076*
C13A1.1161 (2)0.5697 (2)0.11083 (9)0.0491 (4)
H13A1.20640.58090.09360.059*
C14A1.11908 (17)0.89096 (17)0.10031 (8)0.0391 (3)
C15A1.1670 (2)0.9576 (2)0.04791 (10)0.0500 (4)
H15A1.10470.97540.00380.060*
C16A1.3061 (2)0.9976 (2)0.06079 (12)0.0609 (5)
H16A1.33781.04070.02500.073*
C17A1.3989 (2)0.9746 (2)0.12582 (12)0.0594 (5)
H17A1.49151.00390.13440.071*
C18A1.3531 (2)0.9083 (3)0.17757 (11)0.0649 (5)
H18A1.41550.89170.22160.078*
C19A1.2146 (2)0.8655 (2)0.16514 (9)0.0559 (4)
H19A1.18570.81930.20070.067*
C20A0.82246 (17)1.00806 (18)0.11745 (8)0.0400 (3)
C21A0.8104 (2)1.0315 (2)0.18955 (9)0.0488 (4)
H21A0.87770.95290.22090.059*
C22A0.6979 (2)1.1721 (2)0.21449 (11)0.0607 (5)
H22A0.69121.18730.26260.073*
C23A0.5971 (2)1.2884 (2)0.16949 (13)0.0652 (5)
H23A0.52021.38090.18680.078*
C24A0.6096 (2)1.2681 (2)0.09873 (13)0.0634 (5)
H24A0.54181.34800.06810.076*
C25A0.7224 (2)1.12958 (19)0.07223 (10)0.0493 (4)
H25A0.73111.11800.02410.059*
C26A0.9017 (3)1.0390 (3)0.18293 (12)0.0714 (5)
H2610.95380.99370.13800.107*
H2630.98361.00900.21570.107*
H2620.85521.15220.17820.107*
O1B0.31293 (14)0.45350 (12)0.37621 (5)0.0440 (2)
O2B0.47236 (14)0.45945 (14)0.26845 (6)0.0500 (3)
O3B0.25027 (18)0.39417 (14)0.19786 (6)0.0551 (3)
H320.163 (3)0.406 (3)0.1816 (12)0.062 (6)*
O4B0.05021 (16)0.65235 (17)0.24352 (7)0.0553 (3)
H420.090 (3)0.743 (3)0.2394 (12)0.069 (7)*
O5B0.00591 (17)0.84545 (13)0.35104 (7)0.0526 (3)
H520.107 (4)0.874 (3)0.3576 (14)0.084 (8)*
O6B0.07427 (12)0.59786 (12)0.49097 (5)0.0394 (2)
C1B0.3571 (2)0.39980 (18)0.30618 (8)0.0431 (3)
H1B0.40870.28400.30730.052*
C2B0.2021 (2)0.44796 (18)0.26809 (8)0.0445 (3)
H2B0.13080.39360.29150.053*
C3B0.10178 (19)0.62449 (17)0.27215 (8)0.0416 (3)
H3B0.16430.68190.24400.050*
C4B0.06732 (18)0.67721 (16)0.34836 (8)0.0407 (3)
H4B0.01000.63260.37460.049*
C5B0.22883 (19)0.62183 (17)0.38259 (8)0.0385 (3)
H5B0.30190.67410.35890.046*
C6B0.19910 (19)0.65638 (18)0.46040 (8)0.0402 (3)
H630.30180.60440.48190.048*
H640.16130.76940.46760.048*
C7B0.04814 (17)0.58957 (16)0.56649 (7)0.0356 (3)
C8B0.11496 (17)0.55913 (17)0.58210 (8)0.0394 (3)
C9B0.1615 (2)0.4821 (2)0.53349 (10)0.0507 (4)
H9B0.09710.45550.49010.061*
C10B0.3025 (2)0.4443 (2)0.54856 (13)0.0646 (5)
H10B0.33280.39410.51500.078*
C11B0.3973 (2)0.4798 (2)0.61202 (14)0.0682 (6)
H11B0.49100.45250.62210.082*
C12B0.3539 (2)0.5559 (3)0.66101 (13)0.0708 (6)
H12B0.41840.58050.70440.085*
C13B0.2129 (2)0.5970 (2)0.64601 (10)0.0564 (4)
H13B0.18510.65000.67930.068*
C14B0.18515 (17)0.44195 (17)0.59409 (8)0.0371 (3)
C15B0.2934 (2)0.32726 (18)0.54781 (9)0.0462 (3)
H15B0.28850.34340.49960.055*
C16B0.4089 (2)0.1890 (2)0.57281 (11)0.0576 (4)
H16B0.48130.11380.54110.069*
C17B0.4176 (2)0.1617 (2)0.64408 (11)0.0602 (5)
H17B0.49560.06880.66050.072*
C18B0.3093 (2)0.2737 (2)0.69066 (10)0.0572 (4)
H18B0.31330.25580.73890.069*
C19B0.1945 (2)0.4127 (2)0.66593 (9)0.0468 (4)
H19B0.12260.48760.69790.056*
C20B0.03483 (18)0.74705 (18)0.59505 (8)0.0382 (3)
C21B0.1630 (2)0.7665 (2)0.62465 (10)0.0520 (4)
H21B0.25590.67830.63450.062*
C22B0.1543 (3)0.9163 (3)0.63984 (11)0.0672 (5)
H22B0.24190.92740.65950.081*
C23B0.0185 (3)1.0479 (2)0.62629 (11)0.0683 (6)
H23B0.01341.14800.63650.082*
C24B0.1096 (3)1.0302 (2)0.59751 (12)0.0690 (5)
H24B0.20251.11900.58820.083*
C25B0.1021 (2)0.8817 (2)0.58215 (10)0.0534 (4)
H25B0.19060.87180.56280.064*
C26B0.6300 (2)0.4008 (3)0.29548 (12)0.0728 (6)
H2640.61750.44200.34160.109*
H2650.70830.43360.26490.109*
H2660.67060.28740.29820.109*
O70.0018 (2)0.3825 (2)0.13088 (9)0.0811 (4)
H710.092 (2)0.449 (3)0.1299 (13)0.082 (9)*
O80.4376 (2)0.4936 (2)0.09441 (9)0.0781 (4)
O90.6599 (2)0.9282 (2)0.38342 (12)0.0916 (5)
O100.1595 (2)1.0518 (2)0.34549 (10)0.0950 (6)
C270.0464 (4)0.3127 (4)0.06554 (15)0.1008 (9)
H2710.00390.39110.02970.151*
H2720.00230.23100.06420.151*
H2730.16640.26760.05730.151*
C280.3102 (5)0.6022 (5)0.05810 (18)0.1225 (12)
H2810.24100.68700.08870.184*
H2820.24330.54970.04290.184*
H2830.35940.64400.01780.184*
H810.387 (3)0.455 (3)0.1307 (15)0.087 (8)*
C290.5938 (4)0.8244 (5)0.42249 (18)0.1127 (10)
H2910.64890.78890.46420.169*
H2920.61150.73480.39430.169*
H2930.47590.87870.43550.169*
H910.613 (5)0.953 (5)0.346 (2)0.130 (14)*
C300.0938 (5)1.1398 (3)0.40562 (15)0.1068 (10)
H3010.13861.22130.40540.160*
H3020.12281.07220.44630.160*
H3030.02591.18710.40710.160*
H1010.120 (4)0.985 (3)0.3435 (16)0.103 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0607 (7)0.0393 (5)0.0398 (6)0.0214 (5)0.0035 (5)0.0041 (4)
O2A0.0580 (7)0.0526 (6)0.0460 (6)0.0301 (5)0.0008 (5)0.0012 (5)
O3A0.0587 (7)0.0506 (6)0.0464 (6)0.0227 (5)0.0109 (5)0.0090 (5)
O4A0.0516 (7)0.0501 (7)0.0653 (7)0.0254 (5)0.0160 (5)0.0013 (5)
O5A0.0555 (7)0.0428 (6)0.0648 (7)0.0238 (5)0.0098 (5)0.0077 (5)
O6A0.0387 (5)0.0512 (6)0.0327 (5)0.0224 (5)0.0017 (4)0.0002 (4)
C1A0.0581 (10)0.0359 (7)0.0424 (8)0.0202 (7)0.0025 (7)0.0004 (6)
C2A0.0467 (8)0.0408 (8)0.0393 (8)0.0148 (6)0.0040 (6)0.0018 (6)
C3A0.0416 (7)0.0436 (7)0.0428 (7)0.0196 (6)0.0047 (6)0.0021 (6)
C4A0.0448 (8)0.0399 (7)0.0410 (7)0.0180 (6)0.0011 (6)0.0014 (5)
C5A0.0440 (8)0.0403 (7)0.0373 (7)0.0179 (6)0.0008 (6)0.0006 (6)
C6A0.0440 (8)0.0526 (8)0.0364 (7)0.0278 (7)0.0015 (6)0.0008 (6)
C7A0.0330 (7)0.0448 (7)0.0321 (7)0.0169 (6)0.0014 (5)0.0006 (5)
C8A0.0405 (8)0.0474 (8)0.0328 (7)0.0216 (6)0.0003 (6)0.0001 (6)
C9A0.0488 (9)0.0592 (10)0.0519 (9)0.0290 (8)0.0051 (7)0.0018 (7)
C10A0.0741 (13)0.0713 (12)0.0601 (11)0.0455 (11)0.0033 (9)0.0106 (9)
C11A0.0933 (16)0.0548 (11)0.0603 (11)0.0403 (11)0.0093 (11)0.0116 (8)
C12A0.0747 (13)0.0458 (9)0.0598 (11)0.0152 (9)0.0024 (9)0.0028 (8)
C13A0.0465 (9)0.0498 (9)0.0478 (8)0.0146 (7)0.0044 (7)0.0017 (7)
C14A0.0329 (7)0.0418 (7)0.0446 (8)0.0163 (6)0.0065 (6)0.0045 (6)
C15A0.0442 (8)0.0528 (9)0.0561 (9)0.0218 (7)0.0012 (7)0.0094 (7)
C16A0.0461 (9)0.0599 (10)0.0847 (13)0.0258 (8)0.0111 (9)0.0125 (9)
C17A0.0350 (8)0.0511 (9)0.0938 (14)0.0194 (7)0.0047 (9)0.0038 (9)
C18A0.0463 (10)0.0843 (13)0.0650 (12)0.0311 (9)0.0080 (8)0.0069 (10)
C19A0.0453 (9)0.0831 (13)0.0472 (9)0.0348 (9)0.0003 (7)0.0004 (8)
C20A0.0323 (7)0.0464 (8)0.0460 (8)0.0211 (6)0.0037 (6)0.0046 (6)
C21A0.0418 (8)0.0609 (10)0.0457 (9)0.0224 (7)0.0067 (7)0.0092 (7)
C22A0.0528 (10)0.0721 (12)0.0614 (11)0.0291 (9)0.0167 (9)0.0268 (9)
C23A0.0461 (9)0.0555 (10)0.0935 (15)0.0190 (8)0.0185 (9)0.0258 (10)
C24A0.0494 (10)0.0484 (9)0.0873 (15)0.0144 (8)0.0026 (9)0.0013 (9)
C25A0.0462 (9)0.0483 (9)0.0551 (10)0.0197 (7)0.0051 (7)0.0001 (7)
C26A0.0729 (13)0.0846 (14)0.0736 (12)0.0527 (12)0.0053 (10)0.0023 (10)
O1B0.0516 (6)0.0404 (5)0.0357 (5)0.0132 (5)0.0033 (4)0.0024 (4)
O2B0.0462 (6)0.0517 (6)0.0476 (6)0.0155 (5)0.0011 (5)0.0006 (5)
O3B0.0622 (8)0.0591 (7)0.0436 (6)0.0208 (6)0.0053 (5)0.0110 (5)
O4B0.0563 (7)0.0523 (7)0.0610 (7)0.0197 (6)0.0206 (6)0.0011 (5)
O5B0.0505 (7)0.0426 (6)0.0617 (7)0.0131 (5)0.0065 (5)0.0060 (5)
O6B0.0424 (5)0.0494 (6)0.0332 (5)0.0254 (5)0.0034 (4)0.0002 (4)
C1B0.0503 (9)0.0349 (7)0.0402 (8)0.0129 (6)0.0009 (6)0.0006 (6)
C2B0.0532 (9)0.0431 (8)0.0395 (8)0.0214 (7)0.0019 (6)0.0034 (6)
C3B0.0457 (8)0.0427 (7)0.0398 (7)0.0200 (6)0.0078 (6)0.0025 (6)
C4B0.0429 (8)0.0390 (7)0.0418 (7)0.0182 (6)0.0015 (6)0.0003 (5)
C5B0.0422 (7)0.0402 (7)0.0360 (7)0.0206 (6)0.0020 (6)0.0009 (5)
C6B0.0409 (8)0.0462 (8)0.0395 (8)0.0239 (6)0.0011 (6)0.0016 (6)
C7B0.0310 (7)0.0432 (7)0.0346 (7)0.0171 (6)0.0021 (5)0.0023 (6)
C8B0.0316 (7)0.0400 (7)0.0474 (8)0.0148 (6)0.0069 (6)0.0079 (6)
C9B0.0453 (9)0.0496 (9)0.0638 (10)0.0249 (7)0.0074 (7)0.0000 (7)
C10B0.0497 (10)0.0568 (10)0.0988 (16)0.0304 (9)0.0179 (10)0.0036 (10)
C11B0.0387 (9)0.0571 (10)0.1128 (17)0.0258 (8)0.0073 (10)0.0174 (11)
C12B0.0452 (10)0.0830 (14)0.0801 (14)0.0270 (10)0.0118 (9)0.0099 (11)
C13B0.0452 (9)0.0735 (12)0.0534 (10)0.0288 (8)0.0035 (7)0.0020 (8)
C14B0.0312 (7)0.0411 (7)0.0433 (8)0.0186 (6)0.0049 (6)0.0036 (6)
C15B0.0441 (8)0.0439 (8)0.0509 (9)0.0161 (7)0.0058 (7)0.0042 (7)
C16B0.0469 (9)0.0463 (9)0.0747 (12)0.0116 (7)0.0055 (8)0.0058 (8)
C17B0.0446 (9)0.0495 (9)0.0840 (14)0.0147 (7)0.0170 (9)0.0174 (9)
C18B0.0497 (10)0.0669 (11)0.0572 (10)0.0245 (8)0.0158 (8)0.0214 (8)
C19B0.0400 (8)0.0542 (9)0.0456 (9)0.0182 (7)0.0033 (6)0.0054 (7)
C20B0.0391 (7)0.0434 (7)0.0334 (7)0.0180 (6)0.0010 (6)0.0021 (5)
C21B0.0512 (9)0.0520 (9)0.0589 (10)0.0237 (8)0.0130 (8)0.0016 (7)
C22B0.0819 (14)0.0739 (13)0.0664 (12)0.0504 (12)0.0126 (10)0.0058 (10)
C23B0.0938 (16)0.0496 (10)0.0679 (12)0.0366 (11)0.0044 (11)0.0116 (9)
C24B0.0683 (12)0.0430 (10)0.0872 (15)0.0132 (9)0.0016 (11)0.0034 (9)
C25B0.0487 (9)0.0473 (9)0.0624 (11)0.0159 (7)0.0073 (8)0.0004 (7)
C26B0.0458 (10)0.0862 (14)0.0765 (13)0.0139 (9)0.0052 (9)0.0009 (11)
O70.0757 (11)0.0799 (10)0.0832 (10)0.0174 (9)0.0141 (8)0.0317 (8)
O80.0870 (11)0.0884 (11)0.0752 (10)0.0520 (9)0.0081 (8)0.0026 (8)
O90.0637 (10)0.1045 (13)0.0961 (13)0.0189 (9)0.0153 (9)0.0075 (10)
O100.0941 (12)0.1056 (13)0.1018 (13)0.0662 (11)0.0450 (10)0.0514 (10)
C270.125 (2)0.0942 (19)0.0813 (16)0.0400 (17)0.0087 (15)0.0334 (14)
C280.149 (3)0.160 (3)0.097 (2)0.094 (3)0.062 (2)0.051 (2)
C290.108 (2)0.132 (3)0.101 (2)0.050 (2)0.0187 (17)0.0295 (19)
C300.148 (3)0.0887 (17)0.0921 (18)0.0670 (18)0.0464 (18)0.0358 (14)
Geometric parameters (Å, º) top
O1A—C1A1.4130 (19)C1B—H1B0.9800
O1A—C5A1.4355 (18)C2B—O3B1.4179 (19)
O2A—C26A1.429 (2)C2B—C3B1.517 (2)
O3A—H310.83 (2)C2B—H2B0.9800
O4A—H410.83 (2)C3B—O4B1.4216 (19)
O5A—H510.795 (18)C3B—C4B1.523 (2)
O6A—C6A1.4296 (17)C3B—H3B0.9800
O6A—C7A1.4389 (17)C4B—O5B1.4248 (18)
C1A—O2A1.407 (2)C4B—C5B1.520 (2)
C1A—C2A1.520 (2)C4B—H4B0.9800
C1A—H1A0.9800C5B—C6B1.512 (2)
C2A—O3A1.4209 (19)C5B—H5B0.9800
C2A—C3A1.512 (2)C6B—H630.9700
C2A—H2A0.9800C6B—H640.9700
C3A—O4A1.4258 (18)C7B—C20B1.529 (2)
C3A—C4A1.522 (2)C7B—C8B1.5313 (19)
C3A—H3A0.9800C7B—C14B1.540 (2)
C4A—O5A1.4199 (18)C8B—C13B1.380 (2)
C4A—C5A1.525 (2)C8B—C9B1.385 (2)
C4A—H4A0.9800C9B—C10B1.383 (2)
C5A—C6A1.507 (2)C9B—H9B0.9300
C5A—H5A0.9800C10B—C11B1.360 (3)
C6A—H610.9700C10B—H10B0.9300
C6A—H620.9700C11B—C12B1.370 (4)
C7A—C14A1.5342 (19)C11B—H11B0.9300
C7A—C8A1.536 (2)C12B—C13B1.400 (3)
C7A—C20A1.537 (2)C12B—H12B0.9300
C8A—C9A1.388 (2)C13B—H13B0.9300
C8A—C13A1.388 (2)C14B—C15B1.388 (2)
C9A—C10A1.382 (3)C14B—C19B1.392 (2)
C9A—H9A0.9300C15B—C16B1.385 (2)
C10A—C11A1.372 (3)C15B—H15B0.9300
C10A—H10A0.9300C16B—C17B1.379 (3)
C11A—C12A1.376 (3)C16B—H16B0.9300
C11A—H11A0.9300C17B—C18B1.379 (3)
C12A—C13A1.384 (3)C17B—H17B0.9300
C12A—H12A0.9300C18B—C19B1.385 (2)
C13A—H13A0.9300C18B—H18B0.9300
C14A—C19A1.382 (2)C19B—H19B0.9300
C14A—C15A1.388 (2)C20B—C21B1.384 (2)
C15A—C16A1.376 (2)C20B—C25B1.386 (2)
C15A—H15A0.9300C21B—C22B1.388 (3)
C16A—C17A1.375 (3)C21B—H21B0.9300
C16A—H16A0.9300C22B—C23B1.368 (3)
C17A—C18A1.366 (3)C22B—H22B0.9300
C17A—H17A0.9300C23B—C24B1.367 (3)
C18A—C19A1.386 (3)C23B—H23B0.9300
C18A—H18A0.9300C24B—C25B1.381 (3)
C19A—H19A0.9300C24B—H24B0.9300
C20A—C25A1.392 (2)C25B—H25B0.9300
C20A—C21A1.395 (2)C26B—H2640.9600
C21A—C22A1.389 (3)C26B—H2650.9600
C21A—H21A0.9300C26B—H2660.9600
C22A—C23A1.363 (3)O7—C271.383 (3)
C22A—H22A0.9300O7—H710.789 (16)
C23A—C24A1.369 (3)O8—C281.404 (4)
C23A—H23A0.9300O8—H810.90 (3)
C24A—C25A1.389 (3)O9—C291.412 (4)
C24A—H24A0.9300O9—H910.85 (4)
C25A—H25A0.9300O10—C301.379 (3)
C26A—H2610.9600O10—H1010.802 (18)
C26A—H2630.9600C27—H2710.9600
C26A—H2620.9600C27—H2720.9600
O1B—C1B1.4130 (18)C27—H2730.9600
O1B—C5B1.4365 (18)C28—H2810.9600
O2B—C26B1.422 (2)C28—H2820.9600
O3B—H320.82 (2)C28—H2830.9600
O4B—H420.77 (3)C29—H2910.9600
O5B—H520.81 (3)C29—H2920.9600
O6B—C6B1.4254 (17)C29—H2930.9600
O6B—C7B1.4366 (17)C30—H3010.9600
C1B—O2B1.411 (2)C30—H3020.9600
C1B—C2B1.517 (2)C30—H3030.9600
C1A—O1A—C5A114.19 (11)O3B—C2B—H2B107.7
C1A—O2A—C26A113.39 (14)C1B—C2B—H2B107.7
C2A—O3A—H31113.4 (15)C3B—C2B—C1B111.89 (12)
C3A—O4A—H41110.3 (14)C3B—C2B—H2B107.7
C4A—O5A—H51104 (2)O4B—C3B—C2B106.85 (12)
C6A—O6A—C7A115.66 (10)O4B—C3B—C4B110.88 (12)
O1A—C1A—C2A109.59 (13)O4B—C3B—H3B109.6
O1A—C1A—H1A108.6C2B—C3B—C4B110.14 (12)
O2A—C1A—O1A112.26 (13)C2B—C3B—H3B109.6
O2A—C1A—C2A109.20 (12)C4B—C3B—H3B109.6
O2A—C1A—H1A108.6O5B—C4B—C3B109.90 (12)
C2A—C1A—H1A108.6O5B—C4B—C5B108.42 (12)
O3A—C2A—C1A109.07 (13)O5B—C4B—H4B109.3
O3A—C2A—C3A111.23 (12)C3B—C4B—H4B109.3
O3A—C2A—H2A108.3C5B—C4B—C3B110.66 (12)
C3A—C2A—C1A111.44 (12)C5B—C4B—H4B109.3
C3A—C2A—H2A108.3O1B—C5B—C4B110.07 (11)
C1A—C2A—H2A108.3O1B—C5B—C6B106.67 (12)
O4A—C3A—C2A106.33 (12)O1B—C5B—H5B109.1
O4A—C3A—C4A110.87 (12)C4B—C5B—H5B109.1
O4A—C3A—H3A109.3C6B—C5B—C4B112.63 (12)
C2A—C3A—C4A111.59 (12)C6B—C5B—H5B109.1
C2A—C3A—H3A109.3O6B—C6B—C5B107.27 (11)
C4A—C3A—H3A109.3O6B—C6B—H63110.3
O5A—C4A—C3A110.08 (12)O6B—C6B—H64110.3
O5A—C4A—C5A108.50 (12)C5B—C6B—H63110.3
O5A—C4A—H4A109.2C5B—C6B—H64110.3
C3A—C4A—C5A110.49 (12)H63—C6B—H64108.5
C3A—C4A—H4A109.2O6B—C7B—C8B104.16 (11)
C5A—C4A—H4A109.2O6B—C7B—C14B110.02 (11)
O1A—C5A—C4A109.63 (12)O6B—C7B—C20B108.11 (11)
O1A—C5A—C6A107.11 (12)C8B—C7B—C14B105.82 (11)
O1A—C5A—H5A109.8C20B—C7B—C8B112.91 (11)
C6A—C5A—C4A110.63 (12)C20B—C7B—C14B115.25 (12)
C6A—C5A—H5A109.8C9B—C8B—C7B120.04 (14)
C4A—C5A—H5A109.8C13B—C8B—C7B121.55 (15)
O6A—C6A—C5A108.56 (12)C13B—C8B—C9B118.26 (15)
O6A—C6A—H61110.0C8B—C9B—H9B119.6
O6A—C6A—H62110.0C10B—C9B—C8B120.88 (18)
C5A—C6A—H61110.0C10B—C9B—H9B119.6
C5A—C6A—H62110.0C9B—C10B—H10B119.7
H61—C6A—H62108.4C11B—C10B—C9B120.7 (2)
O6A—C7A—C8A107.53 (11)C11B—C10B—H10B119.7
O6A—C7A—C14A105.38 (11)C10B—C11B—C12B119.58 (17)
O6A—C7A—C20A110.27 (11)C10B—C11B—H11B120.2
C8A—C7A—C20A115.29 (12)C12B—C11B—H11B120.2
C14A—C7A—C8A112.45 (11)C11B—C12B—C13B120.3 (2)
C14A—C7A—C20A105.50 (11)C11B—C12B—H12B119.8
C9A—C8A—C7A122.39 (14)C13B—C12B—H12B119.8
C9A—C8A—C13A117.77 (15)C8B—C13B—C12B120.29 (19)
C13A—C8A—C7A119.04 (13)C8B—C13B—H13B119.9
C8A—C9A—H9A119.5C12B—C13B—H13B119.9
C10A—C9A—C8A120.97 (17)C15B—C14B—C7B120.41 (13)
C10A—C9A—H9A119.5C15B—C14B—C19B118.08 (14)
C9A—C10A—H10A119.7C19B—C14B—C7B121.26 (13)
C11A—C10A—C9A120.59 (19)C14B—C15B—H15B119.7
C11A—C10A—H10A119.7C16B—C15B—C14B120.60 (16)
C10A—C11A—C12A119.30 (18)C16B—C15B—H15B119.7
C10A—C11A—H11A120.3C15B—C16B—H16B119.6
C12A—C11A—H11A120.3C17B—C16B—C15B120.80 (17)
C11A—C12A—C13A120.31 (19)C17B—C16B—H16B119.6
C11A—C12A—H12A119.8C16B—C17B—C18B119.20 (16)
C13A—C12A—H12A119.8C16B—C17B—H17B120.4
C8A—C13A—H13A119.5C18B—C17B—H17B120.4
C12A—C13A—C8A121.05 (17)C17B—C18B—C19B120.24 (17)
C12A—C13A—H13A119.5C17B—C18B—H18B119.9
C15A—C14A—C7A120.58 (14)C19B—C18B—H18B119.9
C19A—C14A—C7A120.79 (14)C14B—C19B—H19B119.5
C19A—C14A—C15A118.41 (15)C18B—C19B—C14B121.07 (16)
C14A—C15A—H15A119.8C18B—C19B—H19B119.5
C16A—C15A—C14A120.39 (17)C21B—C20B—C7B123.23 (14)
C16A—C15A—H15A119.8C21B—C20B—C25B117.62 (15)
C15A—C16A—H16A119.5C25B—C20B—C7B118.53 (14)
C17A—C16A—C15A120.95 (18)C20B—C21B—C22B120.69 (18)
C17A—C16A—H16A119.5C20B—C21B—H21B119.7
C16A—C17A—H17A120.5C22B—C21B—H21B119.7
C18A—C17A—C16A119.01 (17)C21B—C22B—H22B119.6
C18A—C17A—H17A120.5C23B—C22B—C21B120.79 (19)
C17A—C18A—C19A120.73 (18)C23B—C22B—H22B119.6
C17A—C18A—H18A119.6C24B—C23B—C22B119.11 (17)
C19A—C18A—H18A119.6C24B—C23B—H23B120.4
C14A—C19A—C18A120.49 (17)C22B—C23B—H23B120.4
C14A—C19A—H19A119.8C23B—C24B—C25B120.55 (19)
C18A—C19A—H19A119.8C23B—C24B—H24B119.7
C21A—C20A—C7A121.38 (14)C25B—C24B—H24B119.7
C25A—C20A—C7A119.85 (14)C20B—C25B—H25B119.4
C25A—C20A—C21A118.44 (15)C24B—C25B—C20B121.24 (18)
C20A—C21A—H21A120.0C24B—C25B—H25B119.4
C22A—C21A—C20A119.97 (17)O2B—C26B—H264109.5
C22A—C21A—H21A120.0O2B—C26B—H265109.5
C21A—C22A—H22A119.5O2B—C26B—H266109.5
C23A—C22A—C21A121.01 (19)H264—C26B—H265109.5
C23A—C22A—H22A119.5H264—C26B—H266109.5
C22A—C23A—C24A119.63 (17)H265—C26B—H266109.5
C22A—C23A—H23A120.2C27—O7—H71107.5 (18)
C24A—C23A—H23A120.2C28—O8—H81106.8 (17)
C23A—C24A—C25A120.72 (19)C29—O9—H91107 (3)
C23A—C24A—H24A119.6C30—O10—H101111 (2)
C25A—C24A—H24A119.6O7—C27—H271109.5
C20A—C25A—H25A119.9O7—C27—H272109.5
C24A—C25A—C20A120.18 (17)O7—C27—H273109.5
C24A—C25A—H25A119.9H271—C27—H272109.5
O2A—C26A—H261109.5H271—C27—H273109.5
O2A—C26A—H263109.5H272—C27—H273109.5
O2A—C26A—H262109.5O8—C28—H281109.5
H261—C26A—H262109.5O8—C28—H282109.5
H261—C26A—H263109.5O8—C28—H283109.5
H263—C26A—H262109.5H281—C28—H282109.5
C1B—O1B—C5B114.55 (11)H281—C28—H283109.5
C1B—O2B—C26B112.38 (14)H282—C28—H283109.5
C2B—O3B—H32106.1 (16)O9—C29—H291109.5
C3B—O4B—H42104.3 (17)O9—C29—H292109.5
C4B—O5B—H52110.0 (19)O9—C29—H293109.5
C6B—O6B—C7B117.24 (10)H291—C29—H292109.5
O1B—C1B—C2B110.24 (12)H291—C29—H293109.5
O1B—C1B—H1B108.4H292—C29—H293109.5
O2B—C1B—O1B111.98 (12)O10—C30—H301109.5
O2B—C1B—C2B109.19 (13)O10—C30—H302109.5
O2B—C1B—H1B108.4O10—C30—H303109.5
C2B—C1B—H1B108.4H301—C30—H302109.5
O3B—C2B—C1B108.99 (13)H301—C30—H303109.5
O3B—C2B—C3B112.72 (13)H302—C30—H303109.5
C5A—O1A—C1A—O2A60.07 (16)C5B—O1B—C1B—O2B62.92 (16)
C5A—O1A—C1A—C2A61.44 (16)C5B—O1B—C1B—C2B58.85 (16)
C1A—O1A—C5A—C4A61.81 (16)C1B—O1B—C5B—C4B59.91 (15)
C1A—O1A—C5A—C6A178.11 (13)C1B—O1B—C5B—C6B177.62 (12)
C7A—O6A—C6A—C5A167.89 (12)C7B—O6B—C6B—C5B168.28 (11)
C6A—O6A—C7A—C8A53.73 (15)C6B—O6B—C7B—C8B167.83 (11)
C6A—O6A—C7A—C14A173.89 (11)C6B—O6B—C7B—C14B79.14 (14)
C6A—O6A—C7A—C20A72.73 (15)C6B—O6B—C7B—C20B47.50 (15)
O1A—C1A—O2A—C26A62.37 (17)O1B—C1B—O2B—C26B65.80 (17)
C2A—C1A—O2A—C26A175.89 (14)C2B—C1B—O2B—C26B171.82 (14)
O1A—C1A—C2A—O3A177.58 (12)O2B—C1B—C2B—O3B55.92 (16)
O1A—C1A—C2A—C3A54.39 (17)O1B—C1B—C2B—O3B179.34 (12)
O2A—C1A—C2A—O3A54.24 (16)O2B—C1B—C2B—C3B69.41 (15)
O2A—C1A—C2A—C3A68.95 (16)O1B—C1B—C2B—C3B54.00 (16)
O3A—C2A—C3A—O4A66.55 (16)O3B—C2B—C3B—O4B64.53 (16)
O3A—C2A—C3A—C4A172.44 (13)O3B—C2B—C3B—C4B174.97 (13)
C1A—C2A—C3A—O4A171.50 (13)C1B—C2B—C3B—O4B172.22 (12)
C1A—C2A—C3A—C4A50.49 (17)C1B—C2B—C3B—C4B51.71 (16)
O4A—C3A—C4A—O5A71.51 (16)O4B—C3B—C4B—O5B70.07 (15)
O4A—C3A—C4A—C5A168.67 (12)O4B—C3B—C4B—C5B170.22 (12)
C2A—C3A—C4A—O5A170.16 (13)C2B—C3B—C4B—O5B171.88 (12)
C2A—C3A—C4A—C5A50.34 (17)C2B—C3B—C4B—C5B52.17 (15)
O5A—C4A—C5A—O1A174.91 (12)O5B—C4B—C5B—O1B175.70 (11)
O5A—C4A—C5A—C6A67.18 (16)O5B—C4B—C5B—C6B65.41 (15)
C3A—C4A—C5A—O1A54.15 (16)C3B—C4B—C5B—O1B55.10 (14)
C3A—C4A—C5A—C6A172.05 (13)C3B—C4B—C5B—C6B173.99 (12)
O1A—C5A—C6A—O6A68.42 (15)O1B—C5B—C6B—O6B70.33 (14)
C4A—C5A—C6A—O6A172.14 (12)C4B—C5B—C6B—O6B50.52 (16)
O6A—C7A—C8A—C9A96.59 (16)O6B—C7B—C8B—C9B27.35 (18)
O6A—C7A—C8A—C13A72.94 (16)O6B—C7B—C8B—C13B157.16 (14)
C14A—C7A—C8A—C9A147.85 (14)C14B—C7B—C8B—C9B88.66 (17)
C14A—C7A—C8A—C13A42.63 (18)C14B—C7B—C8B—C13B86.84 (17)
C20A—C7A—C8A—C9A26.9 (2)C20B—C7B—C8B—C9B144.39 (14)
C20A—C7A—C8A—C13A163.62 (13)C20B—C7B—C8B—C13B40.12 (19)
O6A—C7A—C14A—C15A23.67 (18)O6B—C7B—C14B—C15B10.25 (17)
O6A—C7A—C14A—C19A161.74 (14)O6B—C7B—C14B—C19B175.57 (13)
C8A—C7A—C14A—C15A140.52 (15)C8B—C7B—C14B—C15B101.71 (15)
C8A—C7A—C14A—C19A44.89 (19)C8B—C7B—C14B—C19B72.47 (16)
C20A—C7A—C14A—C15A93.02 (16)C20B—C7B—C14B—C15B132.76 (14)
C20A—C7A—C14A—C19A81.57 (17)C20B—C7B—C14B—C19B53.06 (18)
O6A—C7A—C20A—C21A168.10 (13)O6B—C7B—C20B—C21B103.70 (17)
O6A—C7A—C20A—C25A18.56 (17)O6B—C7B—C20B—C25B67.09 (16)
C8A—C7A—C20A—C21A46.12 (18)C8B—C7B—C20B—C21B141.61 (16)
C8A—C7A—C20A—C25A140.54 (14)C8B—C7B—C20B—C25B47.60 (18)
C14A—C7A—C20A—C21A78.59 (16)C14B—C7B—C20B—C21B19.8 (2)
C14A—C7A—C20A—C25A94.76 (15)C14B—C7B—C20B—C25B169.38 (13)
C7A—C8A—C9A—C10A168.77 (15)C7B—C8B—C9B—C10B175.70 (15)
C13A—C8A—C9A—C10A0.9 (2)C13B—C8B—C9B—C10B0.1 (3)
C7A—C8A—C13A—C12A169.03 (15)C7B—C8B—C13B—C12B174.68 (16)
C9A—C8A—C13A—C12A1.0 (2)C9B—C8B—C13B—C12B0.9 (3)
C8A—C9A—C10A—C11A0.0 (3)C8B—C9B—C10B—C11B1.0 (3)
C9A—C10A—C11A—C12A0.7 (3)C9B—C10B—C11B—C12B1.0 (3)
C10A—C11A—C12A—C13A0.6 (3)C10B—C11B—C12B—C13B0.0 (3)
C11A—C12A—C13A—C8A0.2 (3)C11B—C12B—C13B—C8B0.9 (3)
C7A—C14A—C15A—C16A174.47 (15)C7B—C14B—C15B—C16B175.31 (14)
C19A—C14A—C15A—C16A0.2 (3)C19B—C14B—C15B—C16B1.0 (2)
C7A—C14A—C19A—C18A173.60 (17)C7B—C14B—C19B—C18B174.75 (15)
C15A—C14A—C19A—C18A1.1 (3)C15B—C14B—C19B—C18B0.4 (2)
C14A—C15A—C16A—C17A0.9 (3)C14B—C15B—C16B—C17B0.6 (3)
C15A—C16A—C17A—C18A1.3 (3)C15B—C16B—C17B—C18B0.2 (3)
C16A—C17A—C18A—C19A0.4 (3)C16B—C17B—C18B—C19B0.7 (3)
C17A—C18A—C19A—C14A0.8 (3)C17B—C18B—C19B—C14B0.4 (3)
C7A—C20A—C21A—C22A174.82 (15)C7B—C20B—C21B—C22B170.08 (16)
C25A—C20A—C21A—C22A1.4 (2)C25B—C20B—C21B—C22B0.8 (3)
C7A—C20A—C25A—C24A175.73 (15)C7B—C20B—C25B—C24B170.56 (17)
C21A—C20A—C25A—C24A2.2 (2)C21B—C20B—C25B—C24B0.8 (3)
C21A—C22A—C23A—C24A1.6 (3)C20B—C21B—C22B—C23B0.4 (3)
C20A—C21A—C22A—C23A0.5 (3)C21B—C22B—C23B—C24B0.1 (3)
C22A—C23A—C24A—C25A0.8 (3)C22B—C23B—C24B—C25B0.1 (3)
C23A—C24A—C25A—C20A1.1 (3)C23B—C24B—C25B—C20B0.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3A—H31···O100.84 (3)1.88 (3)2.707 (2)169 (2)
O3B—H32···O70.82 (3)1.91 (3)2.713 (2)165 (3)
O4A—H41···O2B0.83 (3)2.02 (2)2.8287 (18)164.5 (19)
O4B—H42···O2Ai0.77 (3)2.15 (3)2.9046 (19)166 (3)
O5A—H51···O80.79 (3)1.87 (3)2.667 (2)175 (4)
O5B—H52···O9i0.81 (4)1.90 (4)2.704 (2)173 (3)
O7—H71···O5Ai0.79 (2)1.98 (2)2.763 (2)170 (3)
O8—H81···O3B0.90 (3)1.84 (3)2.727 (2)170 (3)
O9—H91···O3A0.85 (4)1.91 (4)2.741 (2)167 (4)
O10—H101···O5B0.81 (3)1.95 (3)2.754 (2)170 (3)
C1B—H1B···O3Aii0.982.323.2469 (19)157
C3A—H3A···O4Biii0.982.593.471 (2)149
C3B—H3B···O4A0.982.493.391 (2)153
C15B—H15B···O1B0.932.523.417 (2)161
C25A—H25A···O1A0.932.603.443 (2)151
Symmetry codes: (i) x1, y, z; (ii) x, y1, z; (iii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3A—H31···O100.84 (3)1.88 (3)2.707 (2)169 (2)
O3B—H32···O70.82 (3)1.91 (3)2.713 (2)165 (3)
O4A—H41···O2B0.83 (3)2.02 (2)2.8287 (18)164.5 (19)
O4B—H42···O2Ai0.77 (3)2.15 (3)2.9046 (19)166 (3)
O5A—H51···O80.79 (3)1.87 (3)2.667 (2)175 (4)
O5B—H52···O9i0.81 (4)1.90 (4)2.704 (2)173 (3)
O7—H71···O5Ai0.79 (2)1.98 (2)2.763 (2)170 (3)
O8—H81···O3B0.90 (3)1.84 (3)2.727 (2)170 (3)
O9—H91···O3A0.85 (4)1.91 (4)2.741 (2)167 (4)
O10—H101···O5B0.81 (3)1.95 (3)2.754 (2)170 (3)
C1B—H1B···O3Aii0.982.323.2469 (19)157.00
C3A—H3A···O4Biii0.982.593.471 (2)149.00
C3B—H3B···O4A0.982.493.391 (2)153.00
C15B—H15B···O1B0.932.523.417 (2)161.00
C25A—H25A···O1A0.932.603.443 (2)151.00
Symmetry codes: (i) x1, y, z; (ii) x, y1, z; (iii) x+1, y, z.
 

Acknowledgements

The authors wish to acknowledge the financial support of this work by Çankırı Karatekin University Research Fund (grant No. BAP: 2011/06) and thank Professor Volker Jäger of Stuttgart University, Germany, for helpful discussions.

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Volume 70| Part 4| April 2014| Pages o492-o493
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