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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

16-Iso­propyl-5,9-di­methyl­tetra­cyclo­[10.2.2.01,10.04,9]hexa­dec-15-ene-5,14-di­methanol

aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing, 210042, People's Republic of China
*Correspondence e-mail: shangsb@hotmail.com

(Received 23 December 2010; accepted 6 January 2011; online 12 January 2011)

The title compound, C23H38O2, a tetra­cyclo­[10.2.2.01,10.04,9] hexa­decane structure, crystallized with four independent mol­ecules in the asymmetric unit. In the crystal, these independent mol­ecules are linked by O—H⋯O hydrogen bonds, forming a polymeric chain propagating in [100]

Related literature

For the isolation of acrylic modified rosin, see: Aldrich (1971[Aldrich, P. H. (1971). US Patent No. 3 562 243.]). For the crystal structure of 16-isopropyl-5,9-dimethyl­tetra­cyclo­[10.2.2.01,10.04,9]hexa­dec-15-ene-5,14-dicarb­oxy­lic acid, see: Wang et al. (2009[Wang, H.-X., Shang, S.-B., Yin, Y.-B., Rao, X.-P. & Xu, X. (2009). Acta Cryst. E65, o1521.]).

[Scheme 1]

Experimental

Crystal data
  • C23H38O2

  • Mr = 346.53

  • Monoclinic, P 21

  • a = 12.986 (3) Å

  • b = 25.583 (5) Å

  • c = 14.292 (3) Å

  • β = 116.19 (3)°

  • V = 4260.6 (19) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al. 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.980, Tmax = 0.993

  • 8392 measured reflections

  • 8024 independent reflections

  • 4643 reflections with I > 2σ(I)

  • Rint = 0.028

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.160

  • S = 1.00

  • 8024 reflections

  • 917 parameters

  • 13 restraints

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1O⋯O6i 0.82 1.99 2.717 (6) 148
O2—H2O⋯O7ii 0.85 1.84 2.692 (5) 179
O3—H3O⋯O2iii 0.82 1.92 2.712 (5) 163
O4—H4O⋯O5iv 0.82 2.11 2.694 (5) 128
O5—H5O⋯O8v 0.82 1.92 2.682 (5) 155
O6—H6O⋯O3vi 0.82 2.03 2.704 (6) 139
O7—H7O⋯O4vii 0.82 2.02 2.692 (5) 139
O8—H8O⋯O1viii 0.82 1.87 2.677 (6) 166
Symmetry codes: (i) x-1, y, z-1; (ii) [-x+1, y+{\script{1\over 2}}, -z]; (iii) [-x+1, y-{\script{1\over 2}}, -z+1]; (iv) [-x, y-{\script{1\over 2}}, -z+2]; (v) [-x, y+{\script{1\over 2}}, -z+1]; (vi) [-x+1, y+{\script{1\over 2}}, -z+2]; (vii) x+1, y, z-1; (viii) [-x, y-{\script{1\over 2}}, -z].

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994)[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]; cell refinement: CAD-4 EXPRESS[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]; data reduction: XCAD4 (Harms & Wocadlo,1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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

16-Isopropyl-5,9-dimethyltetracyclo[10.2.2.01,10.04,9]hexadec-15-ene-5,14- dicarboxylic acid was isolated from acrylic modified rosin (Aldrich, 1971), and its crystal structure has been reported previously (Wang et al., 2009). The title compound was obtained on reduction of this dicarboxylic acid.

The molecular structure of one of the independent molecules of the title compound is shown in Fig. 1. The asymmetric unit consists of four crystallographically independent molecules (Fig. 2).

In the crystal the independent molecules are linked via O–H···O hydrogen bonds (Table 1), to form a polymer chain propagating in [100], as illustrated in Fig. 3.

Related literature top

For the isolation of acrylic modified rosin, see: Aldrich (1971). For the crystal structure of 16-isopropyl-5,9-dimethyltetracyclo[10.2.2.01,10.04,9]hexadec-15-ene-5,14-dicarboxylic acid, see: Wang et al. (2009).

Experimental top

16-Isopropyl-5,9-dimethyltetracyclo[10.2.2.01,10.04,9]hexadec-15- ene-5,14-dicarboxylic acid was (20.0 g) dissolved in tetrahydrofuran (300 ml) at 263 K while stirring vigorously, lithium aluminium hydride (8.1 g) was added in batch within 2 h. The reaction was maintained during 1 h at the temperature of reflux, then water (8.1 ml) and 10% sodium hydroxide solution(8.1 ml) were added drop wise at 263 K. The mixture was then filtered and the filtrate was concentrated. The crude product was recrystallized with ethanol, giving the title compound. Crystals, suitable for X-ray diffraction, were obtained by slow evaporation of an ethanol solution.

Refinement top

Only one equivalent of the diffraction data was measured and the absolute structure of the molecules in the crystal are unknown. The structure contains solvent accessible voids of 47 Å3 which could possibly be a disordered water molecule. It was not taken into consideration when refining the crystal structure. The C-C bonds of the isopropyl groups wre refined with distance restraints of 1.50 (2) Å. The OH and the C-bound H-atoms were included in calculated positions and treated as riding atoms: O-H = 0.82 - 0.85 Å, C-H = 0.96, 0.9 and 0.98 Å for CH~3~, CH2 and CH H-atoms, respectively, with Uiso(H) = k ×Ueq of the carrier atom, where k = 1.5 for OH and CH3 H-atoms and 1.2 for all other H-atoms.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo,1995); 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. A view of the molecular structure of one of the four independent molecules of the title compound. The displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A view of the four independent molecules of the title compound. The displacement ellipsoids are drawn at the 30% probability level.
[Figure 3] Fig. 3. A perspective view along the a-axis of the crystal packing of the title compound. The O-H···O hydrogen bonds are shown as dashed lines (see Table 1 for details).
16-Isopropyl-5,9-dimethyltetracyclo[10.2.2.01,10.04,9] hexadec-15-ene-5,14-dimethanol top
Crystal data top
C23H38O2F(000) = 1536
Mr = 346.53Dx = 1.080 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 12.986 (3) Åθ = 9–13°
b = 25.583 (5) ŵ = 0.07 mm1
c = 14.292 (3) ÅT = 293 K
β = 116.19 (3)°Rod, colourless
V = 4260.6 (19) Å30.30 × 0.20 × 0.10 mm
Z = 8
Data collection top
Enraf–Nonius CAD-4
diffractometer
4643 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 25.4°, θmin = 1.6°
ω/2θ scansh = 015
Absorption correction: ψ scan
(North et al. 1968)
k = 030
Tmin = 0.980, Tmax = 0.993l = 1715
8392 measured reflections3 standard reflections every 200 reflections
8024 independent reflections intensity decay: 1%
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0716P)2 + 1.P]
where P = (Fo2 + 2Fc2)/3
8024 reflections(Δ/σ)max < 0.001
917 parametersΔρmax = 0.30 e Å3
13 restraintsΔρmin = 0.14 e Å3
Crystal data top
C23H38O2V = 4260.6 (19) Å3
Mr = 346.53Z = 8
Monoclinic, P21Mo Kα radiation
a = 12.986 (3) ŵ = 0.07 mm1
b = 25.583 (5) ÅT = 293 K
c = 14.292 (3) Å0.30 × 0.20 × 0.10 mm
β = 116.19 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
4643 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al. 1968)
Rint = 0.028
Tmin = 0.980, Tmax = 0.9933 standard reflections every 200 reflections
8392 measured reflections intensity decay: 1%
8024 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05613 restraints
wR(F2) = 0.160H-atom parameters constrained
S = 1.00Δρmax = 0.30 e Å3
8024 reflectionsΔρmin = 0.14 e Å3
917 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
O10.2354 (3)0.50237 (16)0.1961 (3)0.0794 (12)
H1O0.26620.50960.23360.119*
O20.3722 (3)0.62999 (15)0.3156 (3)0.0725 (11)
H2O0.32960.64560.25910.109*
C10.0449 (4)0.4625 (2)0.2538 (4)0.0535 (13)
H1A0.08560.42960.26430.064*
H1B0.01790.46230.18410.064*
C20.1255 (4)0.5069 (2)0.2632 (4)0.0558 (13)
H2A0.08150.53910.24200.067*
H2B0.15870.50070.21530.067*
C30.2223 (4)0.5144 (2)0.3723 (3)0.0488 (12)
C40.1786 (4)0.5106 (2)0.4566 (4)0.0550 (13)
H40.13350.54240.44870.066*
C50.0951 (4)0.4644 (2)0.4462 (4)0.0558 (13)
C60.0028 (4)0.4674 (2)0.3328 (3)0.0474 (12)
H60.03070.50350.32540.057*
C70.1106 (4)0.4331 (2)0.3097 (4)0.0591 (14)
C80.1499 (5)0.4414 (3)0.3969 (4)0.0708 (16)
H8A0.18230.47620.39000.085*
H8B0.21000.41640.38720.085*
C90.0556 (5)0.4353 (3)0.5040 (5)0.086 (2)
H9A0.02770.39960.51370.103*
H9B0.08490.44220.55450.103*
C100.0446 (5)0.4731 (3)0.5230 (4)0.0744 (18)
H10A0.01730.50890.51670.089*
H10B0.10430.46830.59340.089*
C110.2823 (4)0.5151 (3)0.5664 (4)0.0736 (17)
H11A0.27020.54370.60490.088*
H11B0.29010.48300.60530.088*
C120.3907 (5)0.5247 (3)0.5528 (4)0.0805 (19)
H120.45730.52700.62120.097*
C130.4067 (5)0.4803 (3)0.4906 (5)0.087 (2)
C140.3182 (5)0.4761 (2)0.3976 (4)0.0646 (15)
H140.31560.45060.35020.078*
C150.3774 (5)0.5744 (2)0.4934 (4)0.0718 (16)
H15A0.44740.58160.48700.086*
H15B0.36410.60320.53090.086*
C160.2773 (4)0.5701 (2)0.3855 (4)0.0544 (13)
H160.21940.59610.37980.065*
C170.1589 (5)0.4119 (2)0.4722 (5)0.0772 (18)
H17A0.22610.41470.53770.116*
H17B0.18100.40310.41840.116*
H17C0.10940.38520.47680.116*
C180.0901 (5)0.3747 (2)0.3006 (5)0.0719 (16)
H18A0.16000.35580.28320.108*
H18B0.03180.36230.36580.108*
H18C0.06560.36960.24690.108*
C190.2071 (5)0.4487 (2)0.2061 (4)0.0702 (16)
H19A0.18610.43900.15120.084*
H19B0.27500.42870.19560.084*
C200.3157 (5)0.5811 (2)0.3008 (4)0.0657 (15)
H20A0.36720.55350.30110.079*
H20B0.24930.58080.23330.079*
C210.5125 (7)0.4473 (4)0.5347 (7)0.119 (3)
H210.53270.43510.60570.143*
C220.4941 (10)0.4023 (4)0.4569 (9)0.174 (5)
H22A0.56400.38280.47850.261*
H22B0.47260.41650.38860.261*
H22C0.43430.37970.45520.261*
C230.6059 (8)0.4670 (4)0.5227 (8)0.143 (3)
H23A0.66380.44050.54070.214*
H23B0.63670.49670.56750.214*
H23C0.58150.47740.45150.214*
O30.4090 (3)0.10639 (17)0.6457 (3)0.0779 (12)
H3O0.47140.11970.65900.117*
O40.0145 (3)0.16146 (16)0.9101 (3)0.0739 (11)
H4O0.04590.15150.95770.111*
C240.2672 (5)0.2709 (2)0.6054 (5)0.0643 (15)
H24A0.23870.30640.59970.077*
H24B0.32610.26600.67610.077*
C250.3206 (5)0.2640 (2)0.5303 (5)0.0752 (17)
H25A0.26350.27090.45950.090*
H25B0.38300.28880.54730.090*
C260.3656 (5)0.2090 (2)0.5377 (5)0.0750 (17)
H26A0.42540.20320.60780.090*
H26B0.40000.20540.49000.090*
C270.2746 (4)0.1671 (2)0.5129 (4)0.0567 (13)
C280.2137 (4)0.17624 (18)0.5840 (4)0.0471 (11)
H280.27440.17120.65490.057*
C290.1685 (4)0.2326 (2)0.5847 (4)0.0540 (13)
C300.1232 (4)0.1361 (2)0.5736 (4)0.0520 (12)
H30A0.15160.10130.57100.062*
H30B0.05470.14190.50900.062*
C310.0928 (5)0.13969 (19)0.6660 (4)0.0544 (13)
H31A0.03230.11480.65520.065*
H31B0.15960.12960.72910.065*
C320.0538 (4)0.19368 (19)0.6822 (4)0.0462 (11)
C330.1373 (4)0.23639 (19)0.6781 (4)0.0514 (13)
H330.20940.23170.74130.062*
C340.0910 (5)0.2907 (2)0.6884 (5)0.0717 (16)
H34A0.07250.31090.62550.086*
H34B0.14910.30950.74680.086*
C350.0179 (6)0.2836 (2)0.7056 (6)0.0786 (19)
H350.04870.31770.71190.094*
C360.0191 (6)0.2521 (2)0.8076 (5)0.0739 (17)
H36A0.08120.27010.86430.089*
H36B0.04480.24910.82510.089*
C370.0583 (4)0.1983 (2)0.7935 (4)0.0504 (12)
H370.13860.19430.84490.060*
C380.1049 (5)0.2539 (3)0.6168 (5)0.0789 (19)
C390.0663 (4)0.2068 (3)0.6080 (4)0.0636 (15)
H390.11250.18310.55760.076*
C400.0667 (5)0.2474 (2)0.4809 (4)0.0717 (17)
H40A0.09410.26690.43900.108*
H40B0.01340.26830.49430.108*
H40C0.02910.21620.44450.108*
C410.1937 (5)0.1642 (3)0.3966 (4)0.0814 (19)
H41A0.23620.15390.35910.122*
H41B0.15950.19780.37250.122*
H41C0.13460.13890.38510.122*
C420.3345 (5)0.1133 (2)0.5388 (5)0.0676 (16)
H42A0.27630.08620.51700.081*
H42B0.37800.10910.49890.081*
C430.0092 (5)0.1550 (2)0.8113 (4)0.0629 (15)
H43A0.08640.15470.75500.075*
H43B0.02630.12170.81090.075*
C440.2276 (6)0.2714 (3)0.5497 (6)0.098 (2)
H44A0.26170.24210.50190.118*
C450.2956 (6)0.2751 (4)0.6056 (6)0.113 (3)
H45A0.37080.28780.55970.169*
H45B0.25990.29890.66300.169*
H45C0.30190.24130.63150.169*
C460.2399 (7)0.3144 (3)0.4825 (6)0.114 (3)
H46A0.20570.30590.43710.170*
H46B0.20250.34450.52350.170*
H46C0.32000.32180.44160.170*
O50.0878 (3)0.57521 (17)0.9800 (3)0.0851 (13)
H5O0.13500.55910.99230.128*
O60.5896 (3)0.51875 (17)1.2480 (3)0.0789 (12)
H6O0.58050.53341.29490.118*
C470.0097 (5)0.4123 (2)0.9244 (5)0.0778 (18)
H47A0.01740.41500.99490.093*
H47B0.03220.37720.91550.093*
C480.1160 (5)0.4204 (3)0.8479 (6)0.088 (2)
H48A0.12610.41530.77710.106*
H48B0.16340.39510.86140.106*
C490.1524 (5)0.4747 (3)0.8597 (5)0.0824 (19)
H49A0.14770.47830.92900.099*
H49B0.23200.47950.80980.099*
C500.0809 (5)0.5173 (2)0.8434 (4)0.0605 (14)
C510.0462 (4)0.50645 (19)0.9154 (4)0.0556 (13)
H510.05310.51000.98620.067*
C520.0913 (5)0.4509 (2)0.9117 (4)0.0595 (14)
C530.2112 (4)0.4457 (2)1.0075 (4)0.0559 (13)
H530.19740.44941.06930.067*
C540.3000 (4)0.4887 (2)1.0170 (4)0.0520 (13)
C550.2476 (4)0.5429 (2)1.0013 (4)0.0565 (13)
H55A0.29920.56740.99200.068*
H55B0.24110.55281.06400.068*
C560.1297 (4)0.5474 (2)0.9085 (4)0.0558 (13)
H56A0.13690.54230.84440.067*
H56B0.09920.58220.90700.067*
C570.2701 (5)0.3919 (2)1.0186 (5)0.0782 (18)
H57A0.26440.37231.07420.094*
H57B0.23040.37230.95440.094*
C580.3940 (5)0.3974 (3)1.0419 (6)0.088 (2)
H580.43000.36311.04870.105*
C590.4041 (5)0.4290 (3)0.9578 (6)0.086 (2)
C600.3523 (5)0.4776 (3)0.9426 (4)0.0679 (16)
H600.34980.50110.89190.081*
C610.4532 (6)0.4282 (3)1.1390 (6)0.098 (2)
H61A0.53400.43111.15600.117*
H61B0.44680.41021.19600.117*
C620.4005 (5)0.4835 (2)1.1264 (4)0.0636 (14)
H620.36850.48651.17680.076*
C630.1150 (5)0.5702 (3)0.8732 (5)0.0792 (19)
H63A0.07670.59790.85430.095*
H63B0.19700.57510.83260.095*
C640.1094 (5)0.5238 (3)0.7281 (4)0.0779 (18)
H64A0.10150.49080.70010.117*
H64B0.05780.54870.72130.117*
H64C0.18690.53610.69060.117*
C650.0978 (5)0.4385 (3)0.8078 (5)0.0758 (17)
H65A0.02190.43880.75130.114*
H65B0.13160.40460.81250.114*
H65C0.14390.46440.79560.114*
C660.4910 (5)0.5260 (2)1.1525 (4)0.0645 (15)
H66A0.51450.52771.09690.077*
H66B0.45660.55941.15470.077*
C670.4671 (6)0.4063 (3)0.9017 (6)0.102 (3)
H670.52460.38470.95680.123*
C680.5382 (8)0.4397 (4)0.8765 (8)0.129 (3)
H68A0.58100.41930.84930.194*
H68B0.59040.45780.93810.194*
H68C0.49150.46460.82510.194*
C690.4039 (7)0.3658 (4)0.8217 (7)0.133 (3)
H69A0.45440.35070.79620.199*
H69B0.33980.38170.76480.199*
H69C0.37690.33900.85230.199*
O70.7637 (3)0.17940 (18)0.1371 (3)0.0820 (13)
H7O0.82800.16950.09640.123*
O80.2650 (3)0.05258 (16)0.0216 (3)0.0788 (12)
H8O0.24610.03540.07510.118*
C700.8051 (4)0.1997 (3)0.1952 (4)0.0710 (16)
H70A0.81470.20270.26630.085*
H70B0.82140.16380.18450.085*
C710.8912 (5)0.2354 (3)0.1816 (5)0.085 (2)
H71A0.87870.27120.19650.101*
H71B0.96840.22540.23040.101*
C720.8786 (4)0.2318 (3)0.0714 (4)0.0713 (16)
H72A0.89770.19650.05940.086*
H72B0.93320.25540.06430.086*
C730.7580 (4)0.2452 (2)0.0120 (4)0.0582 (14)
C740.6696 (4)0.2130 (2)0.0078 (4)0.0527 (13)
H740.68630.17690.00360.063*
C750.6798 (4)0.2121 (2)0.1198 (4)0.0523 (13)
C760.5455 (4)0.2203 (2)0.0702 (4)0.0589 (14)
H76A0.54030.22280.13980.071*
H76B0.51650.25260.05530.071*
C770.4717 (4)0.1744 (2)0.0656 (4)0.0578 (14)
H77A0.39260.18070.11540.069*
H77B0.49700.14280.08650.069*
C780.4766 (4)0.1659 (2)0.0420 (4)0.0521 (12)
C790.6066 (4)0.1668 (2)0.1293 (3)0.0512 (12)
H790.64190.13460.12010.061*
C800.6051 (5)0.1621 (3)0.2361 (4)0.0757 (17)
H80A0.65440.13340.27470.091*
H80B0.63550.19390.27550.091*
C810.4834 (5)0.1526 (3)0.2245 (4)0.0773 (19)
H81A0.48450.14930.29320.093*
C820.4364 (6)0.1032 (3)0.1615 (5)0.087 (2)
H82A0.36010.09610.15490.105*
H82B0.48540.07380.19660.105*
C830.4315 (4)0.1105 (2)0.0500 (4)0.0571 (13)
H83A0.48150.08430.04100.069*
C840.4093 (5)0.2043 (2)0.0715 (5)0.0668 (15)
H840.36890.23150.02750.080*
C850.4102 (5)0.1972 (3)0.1668 (5)0.0786 (19)
C860.7501 (5)0.2334 (3)0.1170 (5)0.0762 (18)
H86A0.67590.24520.16910.091*
H86B0.80830.25360.12590.091*
C870.7344 (6)0.3050 (2)0.0182 (6)0.087 (2)
H87A0.65690.31180.06860.131*
H87B0.78650.32270.03860.131*
H87C0.74530.31760.04890.131*
C880.6460 (5)0.2652 (2)0.1501 (5)0.0748 (18)
H88A0.57110.27510.09850.112*
H88B0.70070.29130.15400.112*
H88C0.64520.26210.21670.112*
C890.3108 (5)0.1022 (2)0.0334 (4)0.0671 (15)
H89A0.26200.13020.02990.081*
H89B0.31040.10370.10140.081*
C900.3458 (7)0.2273 (3)0.2128 (7)0.109 (3)
H900.33060.20170.25620.131*
C910.2334 (7)0.2459 (4)0.1414 (7)0.121 (3)
H91A0.19720.26180.18000.182*
H91B0.18760.21700.10180.182*
H91C0.24060.27110.09500.182*
C920.4157 (7)0.2687 (4)0.2882 (6)0.117 (3)
H92A0.37050.28510.31790.176*
H92B0.43890.29440.25240.176*
H92C0.48240.25300.34260.176*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.069 (2)0.080 (3)0.093 (3)0.018 (2)0.040 (2)0.016 (2)
O20.058 (2)0.073 (3)0.078 (3)0.016 (2)0.023 (2)0.014 (2)
C10.055 (3)0.059 (3)0.042 (3)0.007 (3)0.017 (2)0.008 (2)
C20.052 (3)0.069 (4)0.045 (3)0.006 (3)0.020 (2)0.004 (2)
C30.047 (3)0.058 (3)0.039 (3)0.009 (2)0.017 (2)0.002 (2)
C40.056 (3)0.070 (4)0.038 (3)0.009 (3)0.020 (2)0.001 (2)
C50.057 (3)0.062 (4)0.044 (3)0.013 (3)0.018 (3)0.001 (2)
C60.052 (3)0.049 (3)0.037 (3)0.001 (2)0.015 (2)0.000 (2)
C70.056 (3)0.065 (4)0.052 (3)0.007 (3)0.020 (3)0.001 (3)
C80.055 (3)0.087 (5)0.072 (4)0.008 (3)0.030 (3)0.002 (3)
C90.077 (4)0.113 (6)0.062 (4)0.019 (4)0.026 (3)0.012 (4)
C100.065 (4)0.110 (5)0.051 (3)0.017 (4)0.028 (3)0.001 (3)
C110.059 (3)0.104 (5)0.045 (3)0.028 (3)0.011 (3)0.001 (3)
C120.063 (4)0.114 (6)0.046 (3)0.013 (4)0.007 (3)0.012 (4)
C130.060 (4)0.119 (6)0.074 (4)0.000 (4)0.021 (4)0.034 (4)
C140.056 (3)0.073 (4)0.060 (3)0.013 (3)0.020 (3)0.009 (3)
C150.066 (4)0.083 (4)0.055 (3)0.027 (3)0.016 (3)0.005 (3)
C160.054 (3)0.059 (3)0.048 (3)0.004 (3)0.020 (3)0.001 (2)
C170.067 (4)0.067 (4)0.080 (4)0.003 (3)0.016 (3)0.029 (3)
C180.069 (4)0.051 (3)0.091 (4)0.010 (3)0.031 (3)0.007 (3)
C190.056 (3)0.075 (4)0.062 (4)0.002 (3)0.011 (3)0.002 (3)
C200.075 (4)0.073 (4)0.050 (3)0.019 (3)0.028 (3)0.005 (3)
C210.088 (6)0.135 (8)0.130 (7)0.035 (6)0.044 (6)0.034 (6)
C220.163 (10)0.165 (11)0.154 (10)0.046 (9)0.033 (8)0.017 (8)
C230.114 (7)0.133 (8)0.160 (9)0.006 (6)0.042 (7)0.017 (7)
O30.057 (2)0.087 (3)0.085 (3)0.019 (2)0.026 (2)0.023 (2)
O40.077 (3)0.093 (3)0.067 (2)0.018 (2)0.045 (2)0.021 (2)
C240.073 (4)0.050 (3)0.082 (4)0.002 (3)0.045 (3)0.008 (3)
C250.078 (4)0.068 (4)0.099 (5)0.007 (3)0.057 (4)0.020 (3)
C260.072 (4)0.078 (4)0.095 (5)0.005 (3)0.055 (4)0.004 (4)
C270.052 (3)0.063 (3)0.058 (3)0.010 (3)0.026 (3)0.009 (3)
C280.042 (3)0.046 (3)0.046 (3)0.009 (2)0.013 (2)0.005 (2)
C290.058 (3)0.047 (3)0.061 (3)0.000 (2)0.029 (3)0.003 (2)
C300.053 (3)0.053 (3)0.051 (3)0.007 (2)0.023 (3)0.007 (2)
C310.057 (3)0.048 (3)0.060 (3)0.001 (2)0.027 (3)0.001 (2)
C320.041 (3)0.047 (3)0.047 (3)0.002 (2)0.016 (2)0.002 (2)
C330.059 (3)0.040 (3)0.067 (3)0.001 (2)0.039 (3)0.000 (2)
C340.079 (4)0.061 (4)0.089 (4)0.012 (3)0.049 (4)0.000 (3)
C350.103 (5)0.061 (4)0.105 (5)0.035 (4)0.076 (5)0.026 (4)
C360.085 (4)0.071 (4)0.082 (4)0.006 (3)0.052 (4)0.001 (3)
C370.046 (3)0.056 (3)0.046 (3)0.005 (2)0.018 (2)0.003 (2)
C380.072 (4)0.090 (5)0.086 (5)0.038 (4)0.045 (4)0.037 (4)
C390.042 (3)0.093 (5)0.052 (3)0.000 (3)0.017 (3)0.003 (3)
C400.071 (4)0.082 (4)0.060 (3)0.029 (3)0.026 (3)0.029 (3)
C410.085 (4)0.099 (5)0.055 (3)0.021 (4)0.025 (3)0.018 (3)
C420.066 (4)0.068 (4)0.072 (4)0.023 (3)0.033 (3)0.011 (3)
C430.066 (3)0.072 (4)0.062 (3)0.015 (3)0.039 (3)0.004 (3)
C440.073 (4)0.125 (7)0.098 (5)0.023 (4)0.040 (4)0.028 (5)
C450.086 (5)0.130 (7)0.126 (7)0.023 (5)0.051 (5)0.028 (5)
C460.092 (5)0.123 (7)0.120 (6)0.018 (5)0.042 (5)0.045 (5)
O50.074 (3)0.103 (3)0.097 (3)0.012 (2)0.055 (3)0.038 (3)
O60.055 (2)0.098 (3)0.061 (2)0.005 (2)0.0047 (19)0.020 (2)
C470.056 (4)0.072 (4)0.095 (5)0.021 (3)0.024 (3)0.002 (3)
C480.061 (4)0.072 (4)0.116 (6)0.020 (3)0.025 (4)0.016 (4)
C490.058 (4)0.095 (5)0.092 (5)0.002 (4)0.031 (3)0.021 (4)
C500.060 (3)0.062 (3)0.060 (3)0.000 (3)0.026 (3)0.007 (3)
C510.058 (3)0.051 (3)0.063 (3)0.004 (3)0.031 (3)0.014 (3)
C520.065 (3)0.050 (3)0.067 (3)0.005 (3)0.033 (3)0.010 (3)
C530.056 (3)0.042 (3)0.067 (3)0.001 (2)0.024 (3)0.002 (2)
C540.052 (3)0.057 (3)0.054 (3)0.003 (2)0.030 (3)0.003 (2)
C550.064 (3)0.046 (3)0.064 (3)0.002 (3)0.033 (3)0.002 (3)
C560.063 (3)0.049 (3)0.055 (3)0.000 (3)0.026 (3)0.001 (2)
C570.072 (4)0.045 (3)0.098 (5)0.000 (3)0.020 (4)0.005 (3)
C580.064 (4)0.056 (4)0.136 (7)0.003 (3)0.037 (4)0.021 (4)
C590.057 (4)0.084 (5)0.114 (6)0.007 (4)0.034 (4)0.038 (4)
C600.068 (4)0.081 (4)0.065 (4)0.009 (3)0.039 (3)0.020 (3)
C610.072 (4)0.072 (5)0.120 (6)0.005 (4)0.015 (4)0.002 (4)
C620.056 (3)0.065 (4)0.063 (4)0.005 (3)0.020 (3)0.005 (3)
C630.076 (4)0.096 (5)0.075 (4)0.025 (4)0.042 (4)0.009 (4)
C640.080 (4)0.089 (5)0.060 (4)0.015 (4)0.026 (3)0.003 (3)
C650.075 (4)0.078 (4)0.074 (4)0.002 (3)0.032 (3)0.023 (3)
C660.068 (4)0.071 (4)0.056 (3)0.011 (3)0.028 (3)0.009 (3)
C670.083 (5)0.107 (6)0.117 (6)0.002 (4)0.043 (5)0.048 (5)
C680.153 (8)0.114 (7)0.157 (8)0.026 (6)0.102 (7)0.031 (6)
C690.102 (6)0.129 (7)0.166 (8)0.018 (5)0.059 (6)0.078 (7)
O70.067 (2)0.103 (4)0.082 (3)0.009 (2)0.038 (2)0.035 (2)
O80.081 (3)0.074 (3)0.092 (3)0.022 (2)0.048 (3)0.012 (2)
C700.044 (3)0.095 (5)0.058 (3)0.002 (3)0.009 (3)0.009 (3)
C710.038 (3)0.114 (5)0.091 (5)0.011 (3)0.019 (3)0.032 (4)
C720.048 (3)0.092 (5)0.072 (4)0.001 (3)0.025 (3)0.013 (3)
C730.053 (3)0.063 (4)0.065 (4)0.004 (3)0.032 (3)0.004 (3)
C740.040 (3)0.064 (3)0.049 (3)0.008 (2)0.015 (2)0.007 (2)
C750.045 (3)0.063 (3)0.047 (3)0.002 (2)0.019 (2)0.010 (2)
C760.060 (3)0.066 (4)0.049 (3)0.001 (3)0.022 (3)0.011 (3)
C770.046 (3)0.075 (4)0.051 (3)0.004 (3)0.019 (2)0.016 (3)
C780.046 (3)0.057 (3)0.050 (3)0.001 (2)0.018 (2)0.000 (2)
C790.048 (3)0.062 (3)0.039 (3)0.001 (2)0.015 (2)0.002 (2)
C800.070 (4)0.109 (5)0.048 (3)0.003 (4)0.026 (3)0.006 (3)
C810.070 (4)0.127 (6)0.039 (3)0.008 (4)0.028 (3)0.004 (4)
C820.083 (5)0.116 (6)0.058 (4)0.016 (4)0.027 (3)0.021 (4)
C830.051 (3)0.070 (4)0.045 (3)0.004 (3)0.016 (2)0.003 (3)
C840.054 (3)0.070 (4)0.084 (4)0.007 (3)0.037 (3)0.002 (3)
C850.066 (4)0.108 (5)0.077 (4)0.016 (4)0.044 (4)0.029 (4)
C860.067 (4)0.091 (5)0.084 (4)0.006 (3)0.045 (3)0.006 (4)
C870.098 (5)0.055 (4)0.134 (6)0.000 (3)0.075 (5)0.006 (4)
C880.075 (4)0.076 (4)0.085 (4)0.012 (3)0.046 (4)0.037 (3)
C890.063 (4)0.062 (4)0.063 (3)0.015 (3)0.015 (3)0.002 (3)
C900.110 (6)0.118 (7)0.118 (6)0.007 (6)0.068 (6)0.018 (5)
C910.099 (6)0.131 (7)0.130 (7)0.026 (5)0.047 (6)0.014 (6)
C920.119 (6)0.127 (7)0.121 (6)0.009 (6)0.067 (5)0.035 (6)
Geometric parameters (Å, º) top
O1—C191.413 (7)O5—C631.413 (7)
O1—H1O0.8200O5—H5O0.8200
O2—C201.419 (6)O6—C661.412 (6)
O2—H2O0.8504O6—H6O0.8200
C1—C21.510 (7)C47—C521.516 (7)
C1—C61.513 (6)C47—C481.526 (8)
C1—H1A0.9700C47—H47A0.9700
C1—H1B0.9700C47—H47B0.9700
C2—C31.522 (6)C48—C491.499 (9)
C2—H2A0.9700C48—H48A0.9700
C2—H2B0.9700C48—H48B0.9700
C3—C141.500 (7)C49—C501.515 (9)
C3—C41.545 (6)C49—H49A0.9700
C3—C161.566 (7)C49—H49B0.9700
C4—C111.557 (7)C50—C641.529 (7)
C4—C51.566 (7)C50—C511.537 (7)
C4—H40.9800C50—C631.542 (8)
C5—C101.523 (7)C51—C561.541 (7)
C5—C171.534 (8)C51—C521.547 (7)
C5—C61.559 (6)C51—H510.9800
C6—C71.560 (7)C52—C651.557 (7)
C6—H60.9800C52—C531.560 (7)
C7—C191.510 (7)C53—C571.548 (7)
C7—C181.533 (8)C53—C541.557 (7)
C7—C81.555 (7)C53—H530.9800
C8—C91.487 (8)C54—C551.515 (7)
C8—H8A0.9700C54—C601.521 (7)
C8—H8B0.9700C54—C621.538 (7)
C9—C101.546 (8)C55—C561.525 (7)
C9—H9A0.9700C55—H55A0.9700
C9—H9B0.9700C55—H55B0.9700
C10—H10A0.9700C56—H56A0.9700
C10—H10B0.9700C56—H56B0.9700
C11—C121.522 (8)C57—C581.498 (9)
C11—H11A0.9700C57—H57A0.9700
C11—H11B0.9700C57—H57B0.9700
C12—C151.498 (9)C58—C611.481 (9)
C12—C131.512 (10)C58—C591.502 (10)
C12—H120.9800C58—H580.9800
C13—C141.323 (8)C59—C601.384 (9)
C13—C211.493 (9)C59—C671.493 (8)
C14—H140.9300C60—H600.9300
C15—C161.520 (7)C61—C621.547 (8)
C15—H15A0.9700C61—H61A0.9700
C15—H15B0.9700C61—H61B0.9700
C16—C201.525 (7)C62—C661.523 (7)
C16—H160.9800C62—H620.9800
C17—H17A0.9600C63—H63A0.9700
C17—H17B0.9600C63—H63B0.9700
C17—H17C0.9600C64—H64A0.9600
C18—H18A0.9600C64—H64B0.9600
C18—H18B0.9600C64—H64C0.9600
C18—H18C0.9600C65—H65A0.9600
C19—H19A0.9700C65—H65B0.9600
C19—H19B0.9700C65—H65C0.9600
C20—H20A0.9700C66—H66A0.9700
C20—H20B0.9700C66—H66B0.9700
C21—C231.392 (10)C67—C681.417 (9)
C21—C221.544 (11)C67—C691.492 (9)
C21—H210.9800C67—H670.9800
C22—H22A0.9600C68—H68A0.9600
C22—H22B0.9600C68—H68B0.9600
C22—H22C0.9600C68—H68C0.9600
C23—H23A0.9600C69—H69A0.9600
C23—H23B0.9600C69—H69B0.9600
C23—H23C0.9600C69—H69C0.9600
O3—C421.413 (6)O7—C861.437 (7)
O3—H3O0.8201O7—H7O0.8200
O4—C431.453 (6)O8—C891.444 (7)
O4—H4O0.8200O8—H8O0.8199
C24—C251.524 (8)C70—C711.522 (8)
C24—C291.535 (7)C70—C751.537 (7)
C24—H24A0.9700C70—H70A0.9700
C24—H24B0.9700C70—H70B0.9700
C25—C261.511 (8)C71—C721.513 (8)
C25—H25A0.9700C71—H71A0.9700
C25—H25B0.9700C71—H71B0.9700
C26—C271.516 (8)C72—C731.531 (7)
C26—H26A0.9700C72—H72A0.9700
C26—H26B0.9700C72—H72B0.9700
C27—C411.527 (7)C73—C861.489 (8)
C27—C421.543 (7)C73—C741.536 (7)
C27—C281.555 (7)C73—C871.557 (8)
C28—C301.519 (7)C74—C761.513 (7)
C28—C291.559 (7)C74—C751.547 (7)
C28—H280.9800C74—H740.9800
C29—C401.536 (7)C75—C791.542 (7)
C29—C331.560 (7)C75—C881.546 (7)
C30—C311.539 (7)C76—C771.535 (7)
C30—H30A0.9700C76—H76A0.9700
C30—H30B0.9700C76—H76B0.9700
C31—C321.524 (7)C77—C781.526 (6)
C31—H31A0.9700C77—H77A0.9700
C31—H31B0.9700C77—H77B0.9700
C32—C391.486 (7)C78—C841.493 (7)
C32—C331.558 (7)C78—C831.558 (7)
C32—C371.570 (7)C78—C791.597 (6)
C33—C341.546 (7)C79—C801.539 (7)
C33—H330.9800C79—H790.9800
C34—C351.550 (8)C80—C811.534 (8)
C34—H34A0.9700C80—H80A0.9700
C34—H34B0.9700C80—H80B0.9700
C35—C381.483 (9)C81—C851.480 (9)
C35—C361.545 (8)C81—C821.516 (9)
C35—H350.9800C81—H81A0.9800
C36—C371.513 (7)C82—C831.577 (7)
C36—H36A0.9700C82—H82A0.9700
C36—H36B0.9700C82—H82B0.9700
C37—C431.502 (7)C83—C891.508 (7)
C37—H370.9800C83—H83A0.9800
C38—C391.333 (8)C84—C851.370 (8)
C38—C441.520 (8)C84—H840.9300
C39—H390.9300C85—C901.487 (8)
C40—H40A0.9600C86—H86A0.9700
C40—H40B0.9600C86—H86B0.9700
C40—H40C0.9600C87—H87A0.9600
C41—H41A0.9600C87—H87B0.9600
C41—H41B0.9600C87—H87C0.9600
C41—H41C0.9600C88—H88A0.9600
C42—H42A0.9700C88—H88B0.9600
C42—H42B0.9700C88—H88C0.9600
C43—H43A0.9700C89—H89A0.9700
C43—H43B0.9700C89—H89B0.9700
C44—C461.421 (9)C90—C911.443 (9)
C44—C451.432 (9)C90—C921.497 (9)
C44—H44A0.9800C90—H900.9800
C45—H45A0.9600C91—H91A0.9600
C45—H45B0.9600C91—H91B0.9600
C45—H45C0.9600C91—H91C0.9600
C46—H46A0.9600C92—H92A0.9600
C46—H46B0.9600C92—H92B0.9600
C46—H46C0.9600C92—H92C0.9600
C19—O1—H1O109.4C63—O5—H5O109.4
C20—O2—H2O101.3C66—O6—H6O109.5
C2—C1—C6111.5 (4)C52—C47—C48114.1 (5)
C2—C1—H1A109.3C52—C47—H47A108.7
C6—C1—H1A109.3C48—C47—H47A108.7
C2—C1—H1B109.3C52—C47—H47B108.7
C6—C1—H1B109.3C48—C47—H47B108.7
H1A—C1—H1B108.0H47A—C47—H47B107.6
C1—C2—C3114.4 (4)C49—C48—C47109.6 (5)
C1—C2—H2A108.7C49—C48—H48A109.7
C3—C2—H2A108.7C47—C48—H48A109.7
C1—C2—H2B108.7C49—C48—H48B109.7
C3—C2—H2B108.7C47—C48—H48B109.7
H2A—C2—H2B107.6H48A—C48—H48B108.2
C14—C3—C2112.8 (4)C48—C49—C50113.8 (5)
C14—C3—C4108.8 (4)C48—C49—H49A108.8
C2—C3—C4111.7 (4)C50—C49—H49A108.8
C14—C3—C16106.3 (4)C48—C49—H49B108.8
C2—C3—C16111.4 (4)C50—C49—H49B108.8
C4—C3—C16105.6 (4)H49A—C49—H49B107.7
C3—C4—C11109.2 (4)C49—C50—C64111.7 (5)
C3—C4—C5116.8 (4)C49—C50—C51108.5 (5)
C11—C4—C5113.9 (4)C64—C50—C51114.8 (4)
C3—C4—H4105.3C49—C50—C63108.6 (5)
C11—C4—H4105.3C64—C50—C63103.9 (5)
C5—C4—H4105.3C51—C50—C63109.2 (4)
C10—C5—C17108.2 (5)C50—C51—C56114.3 (4)
C10—C5—C6109.2 (4)C50—C51—C52117.0 (4)
C17—C5—C6113.6 (4)C56—C51—C52109.6 (4)
C10—C5—C4108.7 (4)C50—C51—H51104.8
C17—C5—C4111.1 (4)C56—C51—H51104.8
C6—C5—C4105.9 (4)C52—C51—H51104.8
C1—C6—C5110.9 (4)C47—C52—C51107.5 (4)
C1—C6—C7114.8 (4)C47—C52—C65108.4 (5)
C5—C6—C7115.8 (4)C51—C52—C65113.6 (5)
C1—C6—H6104.6C47—C52—C53108.6 (5)
C5—C6—H6104.6C51—C52—C53107.2 (4)
C7—C6—H6104.6C65—C52—C53111.5 (5)
C19—C7—C18105.8 (5)C57—C53—C54107.8 (4)
C19—C7—C8109.0 (5)C57—C53—C52115.0 (4)
C18—C7—C8109.4 (5)C54—C53—C52115.5 (4)
C19—C7—C6109.8 (4)C57—C53—H53105.9
C18—C7—C6113.1 (5)C54—C53—H53105.9
C8—C7—C6109.6 (4)C52—C53—H53105.9
C9—C8—C7113.4 (5)C55—C54—C60112.2 (5)
C9—C8—H8A108.9C55—C54—C62110.8 (4)
C7—C8—H8A108.9C60—C54—C62104.7 (4)
C9—C8—H8B108.9C55—C54—C53111.5 (4)
C7—C8—H8B108.9C60—C54—C53110.4 (4)
H8A—C8—H8B107.7C62—C54—C53106.9 (4)
C8—C9—C10111.3 (5)C54—C55—C56114.3 (4)
C8—C9—H9A109.4C54—C55—H55A108.7
C10—C9—H9A109.4C56—C55—H55A108.7
C8—C9—H9B109.4C54—C55—H55B108.7
C10—C9—H9B109.4C56—C55—H55B108.7
H9A—C9—H9B108.0H55A—C55—H55B107.6
C5—C10—C9112.2 (5)C55—C56—C51110.9 (4)
C5—C10—H10A109.2C55—C56—H56A109.5
C9—C10—H10A109.2C51—C56—H56A109.5
C5—C10—H10B109.2C55—C56—H56B109.5
C9—C10—H10B109.2C51—C56—H56B109.5
H10A—C10—H10B107.9H56A—C56—H56B108.0
C12—C11—C4108.7 (4)C58—C57—C53111.9 (5)
C12—C11—H11A109.9C58—C57—H57A109.2
C4—C11—H11A109.9C53—C57—H57A109.2
C12—C11—H11B109.9C58—C57—H57B109.2
C4—C11—H11B109.9C53—C57—H57B109.2
H11A—C11—H11B108.3H57A—C57—H57B107.9
C15—C12—C13108.5 (5)C61—C58—C57108.7 (6)
C15—C12—C11109.1 (6)C61—C58—C59105.7 (6)
C13—C12—C11109.2 (6)C57—C58—C59109.7 (6)
C15—C12—H12110.0C61—C58—H58110.9
C13—C12—H12110.0C57—C58—H58110.9
C11—C12—H12110.0C59—C58—H58110.9
C14—C13—C21127.4 (8)C60—C59—C67127.5 (8)
C14—C13—C12111.6 (6)C60—C59—C58113.7 (6)
C21—C13—C12121.0 (7)C67—C59—C58118.8 (7)
C13—C14—C3116.7 (6)C59—C60—C54113.2 (6)
C13—C14—H14121.6C59—C60—H60123.4
C3—C14—H14121.6C54—C60—H60123.4
C12—C15—C16110.2 (5)C58—C61—C62110.9 (6)
C12—C15—H15A109.6C58—C61—H61A109.5
C16—C15—H15A109.6C62—C61—H61A109.5
C12—C15—H15B109.6C58—C61—H61B109.5
C16—C15—H15B109.6C62—C61—H61B109.5
H15A—C15—H15B108.1H61A—C61—H61B108.0
C15—C16—C20111.0 (4)C66—C62—C54113.8 (5)
C15—C16—C3109.2 (4)C66—C62—C61111.8 (5)
C20—C16—C3111.3 (4)C54—C62—C61109.4 (5)
C15—C16—H16108.4C66—C62—H62107.2
C20—C16—H16108.4C54—C62—H62107.2
C3—C16—H16108.4C61—C62—H62107.2
C5—C17—H17A109.5O5—C63—C50114.4 (5)
C5—C17—H17B109.5O5—C63—H63A108.7
H17A—C17—H17B109.5C50—C63—H63A108.7
C5—C17—H17C109.5O5—C63—H63B108.7
H17A—C17—H17C109.5C50—C63—H63B108.7
H17B—C17—H17C109.5H63A—C63—H63B107.6
C7—C18—H18A109.5C50—C64—H64A109.5
C7—C18—H18B109.5C50—C64—H64B109.5
H18A—C18—H18B109.5H64A—C64—H64B109.5
C7—C18—H18C109.5C50—C64—H64C109.5
H18A—C18—H18C109.5H64A—C64—H64C109.5
H18B—C18—H18C109.5H64B—C64—H64C109.5
O1—C19—C7114.9 (5)C52—C65—H65A109.5
O1—C19—H19A108.5C52—C65—H65B109.5
C7—C19—H19A108.5H65A—C65—H65B109.5
O1—C19—H19B108.5C52—C65—H65C109.5
C7—C19—H19B108.5H65A—C65—H65C109.5
H19A—C19—H19B107.5H65B—C65—H65C109.5
O2—C20—C16111.9 (4)O6—C66—C62114.5 (5)
O2—C20—H20A109.2O6—C66—H66A108.6
C16—C20—H20A109.2C62—C66—H66A108.6
O2—C20—H20B109.2O6—C66—H66B108.6
C16—C20—H20B109.2C62—C66—H66B108.6
H20A—C20—H20B107.9H66A—C66—H66B107.6
C23—C21—C13115.7 (8)C68—C67—C69115.0 (8)
C23—C21—C2292.7 (8)C68—C67—C59118.3 (7)
C13—C21—C22107.2 (8)C69—C67—C59115.9 (6)
C23—C21—H21113.1C68—C67—H67101.1
C13—C21—H21113.1C69—C67—H67101.1
C22—C21—H21113.1C59—C67—H67101.1
C21—C22—H22A109.5C67—C68—H68A109.5
C21—C22—H22B109.5C67—C68—H68B109.5
H22A—C22—H22B109.5H68A—C68—H68B109.5
C21—C22—H22C109.5C67—C68—H68C109.5
H22A—C22—H22C109.5H68A—C68—H68C109.5
H22B—C22—H22C109.5H68B—C68—H68C109.5
C21—C23—H23A109.5C67—C69—H69A109.5
C21—C23—H23B109.5C67—C69—H69B109.5
H23A—C23—H23B109.5H69A—C69—H69B109.5
C21—C23—H23C109.5C67—C69—H69C109.5
H23A—C23—H23C109.5H69A—C69—H69C109.5
H23B—C23—H23C109.5H69B—C69—H69C109.5
C42—O3—H3O109.5C86—O7—H7O109.5
C43—O4—H4O109.5C89—O8—H8O109.4
C25—C24—C29113.1 (5)C71—C70—C75113.3 (5)
C25—C24—H24A109.0C71—C70—H70A108.9
C29—C24—H24A109.0C75—C70—H70A108.9
C25—C24—H24B109.0C71—C70—H70B108.9
C29—C24—H24B109.0C75—C70—H70B108.9
H24A—C24—H24B107.8H70A—C70—H70B107.7
C26—C25—C24109.9 (5)C72—C71—C70110.4 (5)
C26—C25—H25A109.7C72—C71—H71A109.6
C24—C25—H25A109.7C70—C71—H71A109.6
C26—C25—H25B109.7C72—C71—H71B109.6
C24—C25—H25B109.7C70—C71—H71B109.6
H25A—C25—H25B108.2H71A—C71—H71B108.1
C25—C26—C27113.9 (5)C71—C72—C73113.6 (5)
C25—C26—H26A108.8C71—C72—H72A108.9
C27—C26—H26A108.8C73—C72—H72A108.9
C25—C26—H26B108.8C71—C72—H72B108.9
C27—C26—H26B108.8C73—C72—H72B108.9
H26A—C26—H26B107.7H72A—C72—H72B107.7
C26—C27—C41112.3 (5)C86—C73—C72109.3 (5)
C26—C27—C42108.4 (4)C86—C73—C74110.7 (4)
C41—C27—C42104.4 (5)C72—C73—C74109.2 (4)
C26—C27—C28108.1 (4)C86—C73—C87102.6 (5)
C41—C27—C28114.5 (4)C72—C73—C87111.9 (5)
C42—C27—C28109.0 (4)C74—C73—C87113.1 (5)
C30—C28—C27115.4 (4)C76—C74—C73116.0 (4)
C30—C28—C29110.4 (4)C76—C74—C75109.9 (4)
C27—C28—C29116.4 (4)C73—C74—C75118.0 (4)
C30—C28—H28104.3C76—C74—H74103.6
C27—C28—H28104.3C73—C74—H74103.6
C29—C28—H28104.3C75—C74—H74103.6
C24—C29—C40108.5 (4)C70—C75—C79106.5 (4)
C24—C29—C28107.9 (4)C70—C75—C88109.2 (4)
C40—C29—C28112.8 (4)C79—C75—C88112.0 (4)
C24—C29—C33107.8 (4)C70—C75—C74108.0 (4)
C40—C29—C33111.9 (4)C79—C75—C74109.1 (4)
C28—C29—C33107.7 (4)C88—C75—C74111.8 (4)
C28—C30—C31110.9 (4)C74—C76—C77110.9 (4)
C28—C30—H30A109.5C74—C76—H76A109.5
C31—C30—H30A109.5C77—C76—H76A109.5
C28—C30—H30B109.5C74—C76—H76B109.5
C31—C30—H30B109.5C77—C76—H76B109.5
H30A—C30—H30B108.1H76A—C76—H76B108.0
C32—C31—C30114.4 (4)C78—C77—C76113.8 (4)
C32—C31—H31A108.7C78—C77—H77A108.8
C30—C31—H31A108.7C76—C77—H77A108.8
C32—C31—H31B108.7C78—C77—H77B108.8
C30—C31—H31B108.7C76—C77—H77B108.8
H31A—C31—H31B107.6H77A—C77—H77B107.7
C39—C32—C31114.2 (4)C84—C78—C77114.9 (5)
C39—C32—C33110.1 (4)C84—C78—C83107.0 (4)
C31—C32—C33110.3 (4)C77—C78—C83110.7 (4)
C39—C32—C37105.3 (4)C84—C78—C79108.6 (4)
C31—C32—C37110.8 (4)C77—C78—C79110.2 (4)
C33—C32—C37105.7 (4)C83—C78—C79104.9 (4)
C34—C33—C32108.7 (4)C80—C79—C75115.1 (4)
C34—C33—C29113.3 (4)C80—C79—C78107.6 (4)
C32—C33—C29115.9 (4)C75—C79—C78115.0 (4)
C34—C33—H33106.1C80—C79—H79106.2
C32—C33—H33106.1C75—C79—H79106.2
C29—C33—H33106.1C78—C79—H79106.2
C33—C34—C35109.3 (5)C81—C80—C79111.6 (4)
C33—C34—H34A109.8C81—C80—H80A109.3
C35—C34—H34A109.8C79—C80—H80A109.3
C33—C34—H34B109.8C81—C80—H80B109.3
C35—C34—H34B109.8C79—C80—H80B109.3
H34A—C34—H34B108.3H80A—C80—H80B108.0
C38—C35—C36110.1 (5)C85—C81—C82108.7 (5)
C38—C35—C34109.1 (5)C85—C81—C80108.4 (5)
C36—C35—C34106.6 (5)C82—C81—C80108.8 (6)
C38—C35—H35110.3C85—C81—H81A110.3
C36—C35—H35110.3C82—C81—H81A110.3
C34—C35—H35110.3C80—C81—H81A110.3
C37—C36—C35109.4 (5)C81—C82—C83109.1 (5)
C37—C36—H36A109.8C81—C82—H82A109.9
C35—C36—H36A109.8C83—C82—H82A109.9
C37—C36—H36B109.8C81—C82—H82B109.9
C35—C36—H36B109.8C83—C82—H82B109.9
H36A—C36—H36B108.3H82A—C82—H82B108.3
C43—C37—C36113.1 (4)C89—C83—C78111.2 (4)
C43—C37—C32110.7 (4)C89—C83—C82110.3 (5)
C36—C37—C32109.8 (4)C78—C83—C82109.4 (5)
C43—C37—H37107.7C89—C83—H83A108.6
C36—C37—H37107.7C78—C83—H83A108.6
C32—C37—H37107.7C82—C83—H83A108.6
C39—C38—C35111.6 (5)C85—C84—C78116.3 (5)
C39—C38—C44122.7 (7)C85—C84—H84121.8
C35—C38—C44125.4 (7)C78—C84—H84121.8
C38—C39—C32117.2 (6)C84—C85—C81112.2 (5)
C38—C39—H39121.4C84—C85—C90127.6 (7)
C32—C39—H39121.4C81—C85—C90120.1 (6)
C29—C40—H40A109.5O7—C86—C73115.9 (5)
C29—C40—H40B109.5O7—C86—H86A108.3
H40A—C40—H40B109.5C73—C86—H86A108.3
C29—C40—H40C109.5O7—C86—H86B108.3
H40A—C40—H40C109.5C73—C86—H86B108.3
H40B—C40—H40C109.5H86A—C86—H86B107.4
C27—C41—H41A109.5C73—C87—H87A109.5
C27—C41—H41B109.5C73—C87—H87B109.5
H41A—C41—H41B109.5H87A—C87—H87B109.5
C27—C41—H41C109.5C73—C87—H87C109.5
H41A—C41—H41C109.5H87A—C87—H87C109.5
H41B—C41—H41C109.5H87B—C87—H87C109.5
O3—C42—C27113.8 (5)C75—C88—H88A109.5
O3—C42—H42A108.8C75—C88—H88B109.5
C27—C42—H42A108.8H88A—C88—H88B109.5
O3—C42—H42B108.8C75—C88—H88C109.5
C27—C42—H42B108.8H88A—C88—H88C109.5
H42A—C42—H42B107.7H88B—C88—H88C109.5
O4—C43—C37111.2 (4)O8—C89—C83111.6 (5)
O4—C43—H43A109.4O8—C89—H89A109.3
C37—C43—H43A109.4C83—C89—H89A109.3
O4—C43—H43B109.4O8—C89—H89B109.3
C37—C43—H43B109.4C83—C89—H89B109.3
H43A—C43—H43B108.0H89A—C89—H89B108.0
C46—C44—C45114.3 (7)C91—C90—C85116.7 (7)
C46—C44—C38115.4 (6)C91—C90—C92112.3 (7)
C45—C44—C38113.7 (6)C85—C90—C92113.8 (6)
C46—C44—H44A103.9C91—C90—H90104.1
C45—C44—H44A103.9C85—C90—H90104.1
C38—C44—H44A103.9C92—C90—H90104.1
C44—C45—H45A109.5C90—C91—H91A109.5
C44—C45—H45B109.5C90—C91—H91B109.5
H45A—C45—H45B109.5H91A—C91—H91B109.5
C44—C45—H45C109.5C90—C91—H91C109.5
H45A—C45—H45C109.5H91A—C91—H91C109.5
H45B—C45—H45C109.5H91B—C91—H91C109.5
C44—C46—H46A109.5C90—C92—H92A109.5
C44—C46—H46B109.5C90—C92—H92B109.5
H46A—C46—H46B109.5H92A—C92—H92B109.5
C44—C46—H46C109.5C90—C92—H92C109.5
H46A—C46—H46C109.5H92A—C92—H92C109.5
H46B—C46—H46C109.5H92B—C92—H92C109.5
C6—C1—C2—C353.8 (6)C52—C47—C48—C4958.0 (8)
C1—C2—C3—C1478.9 (5)C47—C48—C49—C5057.5 (8)
C1—C2—C3—C444.0 (6)C48—C49—C50—C6474.2 (7)
C1—C2—C3—C16161.8 (4)C48—C49—C50—C5153.3 (7)
C14—C3—C4—C1151.3 (6)C48—C49—C50—C63171.8 (5)
C2—C3—C4—C11176.4 (5)C49—C50—C51—C56179.1 (5)
C16—C3—C4—C1162.4 (5)C64—C50—C51—C5655.2 (6)
C14—C3—C4—C579.7 (5)C63—C50—C51—C5660.9 (6)
C2—C3—C4—C545.4 (6)C49—C50—C51—C5250.8 (6)
C16—C3—C4—C5166.6 (4)C64—C50—C51—C5274.9 (6)
C3—C4—C5—C10169.4 (5)C63—C50—C51—C52169.0 (5)
C11—C4—C5—C1061.7 (6)C48—C47—C52—C5152.9 (7)
C3—C4—C5—C1771.6 (6)C48—C47—C52—C6570.2 (7)
C11—C4—C5—C1757.3 (6)C48—C47—C52—C53168.5 (5)
C3—C4—C5—C652.3 (6)C50—C51—C52—C4750.6 (6)
C11—C4—C5—C6178.9 (5)C56—C51—C52—C47177.1 (5)
C2—C1—C6—C562.5 (5)C50—C51—C52—C6569.3 (6)
C2—C1—C6—C7163.7 (4)C56—C51—C52—C6563.0 (6)
C10—C5—C6—C1176.3 (5)C50—C51—C52—C53167.2 (4)
C17—C5—C6—C162.9 (6)C56—C51—C52—C5360.5 (5)
C4—C5—C6—C159.4 (5)C47—C52—C53—C5763.3 (6)
C10—C5—C6—C750.5 (6)C51—C52—C53—C57179.1 (5)
C17—C5—C6—C770.3 (6)C65—C52—C53—C5756.0 (6)
C4—C5—C6—C7167.4 (4)C47—C52—C53—C54170.1 (5)
C1—C6—C7—C1960.9 (6)C51—C52—C53—C5454.3 (6)
C5—C6—C7—C19167.7 (5)C65—C52—C53—C5470.6 (6)
C1—C6—C7—C1857.1 (6)C57—C53—C54—C55177.0 (5)
C5—C6—C7—C1874.3 (6)C52—C53—C54—C5546.8 (6)
C1—C6—C7—C8179.4 (4)C57—C53—C54—C6051.6 (6)
C5—C6—C7—C848.0 (6)C52—C53—C54—C6078.6 (6)
C19—C7—C8—C9170.9 (5)C57—C53—C54—C6261.8 (5)
C18—C7—C8—C973.8 (6)C52—C53—C54—C62168.0 (4)
C6—C7—C8—C950.7 (7)C60—C54—C55—C5678.9 (5)
C7—C8—C9—C1056.9 (8)C62—C54—C55—C56164.5 (4)
C17—C5—C10—C970.0 (6)C53—C54—C55—C5645.6 (6)
C6—C5—C10—C954.1 (6)C54—C55—C56—C5154.5 (6)
C4—C5—C10—C9169.2 (5)C50—C51—C56—C55164.1 (4)
C8—C9—C10—C559.2 (7)C52—C51—C56—C5562.2 (6)
C3—C4—C11—C123.1 (7)C54—C53—C57—C583.9 (7)
C5—C4—C11—C12135.7 (5)C52—C53—C57—C58134.3 (6)
C4—C11—C12—C1560.1 (7)C53—C57—C58—C6157.9 (8)
C4—C11—C12—C1358.3 (7)C53—C57—C58—C5957.3 (7)
C15—C12—C13—C1459.4 (7)C61—C58—C59—C6061.3 (7)
C11—C12—C13—C1459.4 (7)C57—C58—C59—C6055.8 (7)
C15—C12—C13—C21120.3 (7)C61—C58—C59—C67118.2 (6)
C11—C12—C13—C21120.9 (7)C57—C58—C59—C67124.8 (6)
C21—C13—C14—C3179.8 (6)C67—C59—C60—C54177.6 (6)
C12—C13—C14—C30.2 (8)C58—C59—C60—C541.8 (7)
C2—C3—C14—C13179.2 (5)C55—C54—C60—C59178.0 (5)
C4—C3—C14—C1356.4 (6)C62—C54—C60—C5957.8 (6)
C16—C3—C14—C1356.9 (6)C53—C54—C60—C5957.0 (6)
C13—C12—C15—C1657.1 (7)C57—C58—C61—C6260.8 (8)
C11—C12—C15—C1661.7 (7)C59—C58—C61—C6256.9 (7)
C12—C15—C16—C20123.7 (6)C55—C54—C62—C6653.2 (6)
C12—C15—C16—C30.6 (7)C60—C54—C62—C6667.9 (6)
C14—C3—C16—C1553.7 (5)C53—C54—C62—C66174.9 (4)
C2—C3—C16—C15176.9 (4)C55—C54—C62—C61179.0 (5)
C4—C3—C16—C1561.7 (5)C60—C54—C62—C6157.9 (6)
C14—C3—C16—C2069.2 (5)C53—C54—C62—C6159.3 (6)
C2—C3—C16—C2054.0 (6)C58—C61—C62—C66125.4 (6)
C4—C3—C16—C20175.3 (4)C58—C61—C62—C541.5 (8)
C18—C7—C19—O1176.5 (5)C49—C50—C63—O565.7 (6)
C8—C7—C19—O165.9 (6)C64—C50—C63—O5175.3 (5)
C6—C7—C19—O154.2 (7)C51—C50—C63—O552.4 (7)
C15—C16—C20—O254.4 (6)C54—C62—C66—O6173.7 (4)
C3—C16—C20—O2176.3 (4)C61—C62—C66—O649.1 (7)
C14—C13—C21—C2394.8 (11)C60—C59—C67—C6838.7 (11)
C12—C13—C21—C2384.9 (10)C58—C59—C67—C68140.7 (8)
C14—C13—C21—C227.0 (11)C60—C59—C67—C69104.0 (9)
C12—C13—C21—C22173.4 (7)C58—C59—C67—C6976.6 (10)
C29—C24—C25—C2658.6 (7)C75—C70—C71—C7258.5 (7)
C24—C25—C26—C2759.1 (7)C70—C71—C72—C7357.4 (7)
C25—C26—C27—C4173.3 (6)C71—C72—C73—C86172.2 (5)
C25—C26—C27—C42171.9 (5)C71—C72—C73—C7451.0 (7)
C25—C26—C27—C2854.0 (6)C71—C72—C73—C8774.9 (7)
C26—C27—C28—C30177.1 (4)C86—C73—C74—C7657.7 (6)
C41—C27—C28—C3056.9 (6)C72—C73—C74—C76178.0 (5)
C42—C27—C28—C3059.5 (5)C87—C73—C74—C7656.7 (7)
C26—C27—C28—C2951.0 (6)C86—C73—C74—C75168.8 (5)
C41—C27—C28—C2975.0 (6)C72—C73—C74—C7548.4 (6)
C42—C27—C28—C29168.6 (4)C87—C73—C74—C7576.8 (6)
C25—C24—C29—C4069.1 (6)C71—C70—C75—C79169.6 (5)
C25—C24—C29—C2853.4 (6)C71—C70—C75—C8869.3 (6)
C25—C24—C29—C33169.5 (4)C71—C70—C75—C7452.5 (6)
C30—C28—C29—C24174.9 (4)C76—C74—C75—C70174.9 (5)
C27—C28—C29—C2450.9 (5)C73—C74—C75—C7049.0 (6)
C30—C28—C29—C4065.3 (5)C76—C74—C75—C7959.4 (5)
C27—C28—C29—C4068.9 (5)C73—C74—C75—C79164.5 (4)
C30—C28—C29—C3358.8 (5)C76—C74—C75—C8864.9 (5)
C27—C28—C29—C33167.1 (4)C73—C74—C75—C8871.2 (6)
C27—C28—C30—C31164.4 (4)C73—C74—C76—C77160.6 (4)
C29—C28—C30—C3160.9 (5)C75—C74—C76—C7762.3 (6)
C28—C30—C31—C3255.6 (6)C74—C76—C77—C7857.4 (6)
C30—C31—C32—C3977.3 (5)C76—C77—C78—C8475.7 (6)
C30—C31—C32—C3347.3 (5)C76—C77—C78—C83163.0 (4)
C30—C31—C32—C37164.0 (4)C76—C77—C78—C7947.4 (6)
C39—C32—C33—C3449.8 (6)C70—C75—C79—C8065.6 (6)
C31—C32—C33—C34176.7 (4)C88—C75—C79—C8053.8 (6)
C37—C32—C33—C3463.5 (5)C74—C75—C79—C80178.1 (4)
C39—C32—C33—C2979.1 (5)C70—C75—C79—C78168.6 (4)
C31—C32—C33—C2947.8 (5)C88—C75—C79—C7872.0 (5)
C37—C32—C33—C29167.6 (4)C74—C75—C79—C7852.3 (5)
C24—C29—C33—C3463.8 (6)C84—C78—C79—C8049.3 (6)
C40—C29—C33—C3455.5 (6)C77—C78—C79—C80175.9 (5)
C28—C29—C33—C34180.0 (4)C83—C78—C79—C8064.9 (5)
C24—C29—C33—C32169.6 (4)C84—C78—C79—C7580.3 (5)
C40—C29—C33—C3271.1 (5)C77—C78—C79—C7546.3 (6)
C28—C29—C33—C3253.5 (5)C83—C78—C79—C75165.6 (4)
C32—C33—C34—C353.3 (6)C75—C79—C80—C81135.3 (5)
C29—C33—C34—C35133.6 (5)C78—C79—C80—C815.8 (7)
C33—C34—C35—C3858.3 (6)C79—C80—C81—C8559.9 (7)
C33—C34—C35—C3660.5 (7)C79—C80—C81—C8258.2 (7)
C38—C35—C36—C3754.0 (6)C85—C81—C82—C8356.9 (6)
C34—C35—C36—C3764.2 (7)C80—C81—C82—C8360.9 (7)
C35—C36—C37—C43121.4 (5)C84—C78—C83—C8968.6 (6)
C35—C36—C37—C322.8 (6)C77—C78—C83—C8957.3 (6)
C39—C32—C37—C4369.6 (5)C79—C78—C83—C89176.1 (4)
C31—C32—C37—C4354.4 (5)C84—C78—C83—C8253.5 (6)
C33—C32—C37—C43173.8 (4)C77—C78—C83—C82179.4 (4)
C39—C32—C37—C3655.9 (5)C79—C78—C83—C8261.8 (5)
C31—C32—C37—C36179.9 (4)C81—C82—C83—C89122.6 (6)
C33—C32—C37—C3660.6 (5)C81—C82—C83—C780.0 (7)
C36—C35—C38—C3956.5 (7)C77—C78—C84—C85178.9 (5)
C34—C35—C38—C3960.1 (7)C83—C78—C84—C8555.5 (6)
C36—C35—C38—C44117.5 (6)C79—C78—C84—C8557.3 (6)
C34—C35—C38—C44125.9 (6)C78—C84—C85—C812.1 (8)
C35—C38—C39—C322.7 (7)C78—C84—C85—C90176.1 (6)
C44—C38—C39—C32176.9 (5)C82—C81—C85—C8461.0 (7)
C31—C32—C39—C38178.8 (5)C80—C81—C85—C8457.1 (7)
C33—C32—C39—C3854.0 (6)C82—C81—C85—C90117.4 (6)
C37—C32—C39—C3859.4 (6)C80—C81—C85—C90124.5 (6)
C26—C27—C42—O363.9 (6)C72—C73—C86—O763.6 (6)
C41—C27—C42—O3176.2 (5)C74—C73—C86—O756.6 (6)
C28—C27—C42—O353.5 (6)C87—C73—C86—O7177.6 (5)
C36—C37—C43—O451.1 (6)C78—C83—C89—O8175.5 (4)
C32—C37—C43—O4174.8 (4)C82—C83—C89—O853.9 (6)
C39—C38—C44—C46116.5 (9)C84—C85—C90—C9134.4 (11)
C35—C38—C44—C4670.2 (9)C81—C85—C90—C91143.6 (8)
C39—C38—C44—C45108.7 (8)C84—C85—C90—C9298.9 (9)
C35—C38—C44—C4564.6 (10)C81—C85—C90—C9283.1 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O6i0.821.992.717 (6)148
O2—H2O···O7ii0.851.842.692 (5)179
O3—H3O···O2iii0.821.922.712 (5)163
O4—H4O···O5iv0.822.112.694 (5)128
O5—H5O···O8v0.821.922.682 (5)155
O6—H6O···O3vi0.822.032.704 (6)139
O7—H7O···O4vii0.822.022.692 (5)139
O8—H8O···O1viii0.821.872.677 (6)166
Symmetry codes: (i) x1, y, z1; (ii) x+1, y+1/2, z; (iii) x+1, y1/2, z+1; (iv) x, y1/2, z+2; (v) x, y+1/2, z+1; (vi) x+1, y+1/2, z+2; (vii) x+1, y, z1; (viii) x, y1/2, z.

Experimental details

Crystal data
Chemical formulaC23H38O2
Mr346.53
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)12.986 (3), 25.583 (5), 14.292 (3)
β (°) 116.19 (3)
V3)4260.6 (19)
Z8
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al. 1968)
Tmin, Tmax0.980, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
8392, 8024, 4643
Rint0.028
(sin θ/λ)max1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.160, 1.00
No. of reflections8024
No. of parameters917
No. of restraints13
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.14

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O6i0.821.992.717 (6)148
O2—H2O···O7ii0.851.842.692 (5)179
O3—H3O···O2iii0.821.922.712 (5)163
O4—H4O···O5iv0.822.112.694 (5)128
O5—H5O···O8v0.821.922.682 (5)155
O6—H6O···O3vi0.822.032.704 (6)139
O7—H7O···O4vii0.822.022.692 (5)139
O8—H8O···O1viii0.821.872.677 (6)166
Symmetry codes: (i) x1, y, z1; (ii) x+1, y+1/2, z; (iii) x+1, y1/2, z+1; (iv) x, y1/2, z+2; (v) x, y+1/2, z+1; (vi) x+1, y+1/2, z+2; (vii) x+1, y, z1; (viii) x, y1/2, z.
 

References

First citationAldrich, P. H. (1971). US Patent No. 3 562 243.  Google Scholar
First citationEnraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, H.-X., Shang, S.-B., Yin, Y.-B., Rao, X.-P. & Xu, X. (2009). Acta Cryst. E65, o1521.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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