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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2163.
Published online 2008 October 22. doi:  10.1107/S1600536808033163
PMCID: PMC2959616

17-(5-Ethyl-6-methyl­heptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra­deca­hydro-1H-cyclo­penta[a]phenanthrene-3,7-diol from Chisocheton tomentosus (Meliaceae)

Abstract

The asymmetric unit of the title compound, C29H50O2, contains two mol­ecules; one mol­ecule is linked to the other by two O—H(...)O hydrogen bonds, whereas only one of the hydr­oxy groups of the second mol­ecule is involved in hydrogen bonding. This gives rise to a chain that runs along the a axis of the monoclinic unit cell.

Related literature

This study is the first on Chisocheton tomentosus. For literature on other Chisocheton species, see: Awang et al. (2007 [triangle]); Bordoloi et al. (1993 [triangle]); Gunning et al. (1994 [triangle]); Inada et al. (1993 [triangle]); Phongmaykin et al. (2008 [triangle]); Tzouros et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2163-scheme1.jpg

Experimental

Crystal data

  • C29H50O2
  • M r = 430.69
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2163-efi1.jpg
  • a = 8.1690 (1) Å
  • b = 12.2369 (2) Å
  • c = 25.6945 (4) Å
  • β = 93.652 (1)°
  • V = 2563.29 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 100 (2) K
  • 0.45 × 0.15 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 21218 measured reflections
  • 6154 independent reflections
  • 5389 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.172
  • S = 1.11
  • 6154 reflections
  • 575 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033163/bt2810sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033163/bt2810Isup2.hkl

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

Acknowledgments

The authors thank the University of Malaya (PPP P8198-2008A) for supporting this study.

supplementary crystallographic information

Experimental

Dried ground bark of Chisocheton tomentosus (3.5 kg) was defatted with hexane for 5 days. The solvent was removed and the plant material dried before being extracted with dichloromethane for another 5 days. The dichloromethane was removed by evaporation to give a crude material (10 g) that was subjected to column chromatography over silica gel. Separation was effected with hexane/dichloromethane (95:5 v/v). The polarity was increased with acetone, and finally with acetone/methanol to give 24 fractions. One of the later fractions was subjected to column chromatography (25:25:50 v/v acetone/dichloromethane/hexane) to give five other fractions. The third fraction yielded colorless crystals when the solvents were allowed to evaporate.

Refinement

In the absence of significant anomalous dispersion effects, Friedel pairs were averaged. Carbon- and oxygen-bound H-atoms were placed in calculated positions (C—H 0.95–1.00, O–H 0.84 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C,O).

Figures

Fig. 1.
70% Probability displacement ellipsoid plot (Barbour, 2001) of C29H50O2. Hydrogen atoms are drawn as spheres of arbitrary radii.

Crystal data

C29H50O2F(000) = 960
Mr = 430.69Dx = 1.116 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7107 reflections
a = 8.1690 (1) Åθ = 2.3–28.3°
b = 12.2369 (2) ŵ = 0.07 mm1
c = 25.6945 (4) ÅT = 100 K
β = 93.652 (1)°Prism, colourless
V = 2563.29 (7) Å30.45 × 0.15 × 0.03 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer5389 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
graphiteθmax = 27.5°, θmin = 0.8°
ω scansh = −10→10
21218 measured reflectionsk = −14→15
6154 independent reflectionsl = −33→33

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.1065P)2 + 0.6901P] where P = (Fo2 + 2Fc2)/3
6154 reflections(Δ/σ)max = 0.001
575 parametersΔρmax = 0.46 e Å3
1 restraintΔρmin = −0.27 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.6382 (2)0.7500 (2)0.97759 (9)0.0231 (5)
H1O0.61620.73290.94630.035*
O2−0.0206 (3)0.7449 (2)1.12076 (9)0.0297 (6)
H2O−0.01180.73381.08880.045*
O3−0.0524 (3)0.7160 (2)1.01700 (9)0.0293 (6)
H3O−0.14370.73261.00220.044*
O40.5741 (3)0.6943 (2)0.87412 (9)0.0243 (5)
H4O0.64880.67840.85440.036*
C10.5203 (3)0.7010 (3)1.00956 (12)0.0204 (6)
H10.41140.69960.98950.024*
C20.5068 (4)0.7730 (3)1.05748 (12)0.0222 (6)
H2A0.61580.77911.07640.027*
H2B0.47160.84721.04630.027*
C30.3855 (4)0.7269 (2)1.09368 (11)0.0188 (6)
C40.4110 (3)0.6076 (2)1.11020 (12)0.0171 (6)
C50.5651 (4)0.6019 (3)1.14821 (12)0.0227 (6)
H5A0.54060.63431.18170.034*
H5B0.65490.64241.13350.034*
H5C0.59750.52541.15350.034*
C60.4381 (4)0.5384 (3)1.06090 (12)0.0197 (6)
H6A0.47370.46411.07200.024*
H6B0.33210.53111.04030.024*
C70.5650 (4)0.5859 (3)1.02586 (13)0.0218 (6)
H7A0.67430.58581.04490.026*
H7B0.57120.53960.99450.026*
C80.2635 (4)0.7893 (3)1.10964 (12)0.0230 (6)
H80.25490.86171.09650.028*
C90.1395 (4)0.7532 (3)1.14665 (12)0.0214 (6)
H90.13420.81121.17390.026*
C100.1912 (4)0.6469 (2)1.17448 (11)0.0178 (6)
H100.28230.66371.20110.021*
C110.2546 (4)0.5652 (2)1.13538 (12)0.0175 (6)
H110.16720.55891.10650.021*
C120.0496 (4)0.5984 (3)1.20216 (12)0.0197 (6)
H12−0.03820.58171.17440.024*
C130.0879 (4)0.4906 (3)1.23062 (12)0.0193 (6)
C140.2300 (4)0.5024 (3)1.27277 (13)0.0235 (6)
H14A0.19410.54721.30150.035*
H14B0.32370.53751.25760.035*
H14C0.26250.42991.28600.035*
C150.1318 (4)0.4089 (3)1.18813 (13)0.0234 (7)
H15A0.15950.33741.20440.028*
H15B0.03570.39851.16310.028*
C160.2773 (4)0.4499 (2)1.15891 (13)0.0228 (7)
H16A0.29710.39791.13050.027*
H16B0.37630.45001.18320.027*
C17−0.0307 (4)0.6698 (3)1.24235 (13)0.0272 (7)
H17A−0.10210.72621.22510.033*
H17B0.05290.70591.26600.033*
C18−0.1323 (4)0.5869 (3)1.27215 (13)0.0278 (7)
H18A−0.25070.59681.26270.033*
H18B−0.11310.59791.31020.033*
C19−0.0770 (4)0.4705 (3)1.25683 (13)0.0229 (6)
H19−0.15840.44301.22910.028*
C20−0.0783 (4)0.3906 (3)1.30303 (14)0.0249 (7)
H20−0.00440.42111.33200.030*
C21−0.0136 (5)0.2765 (3)1.28981 (17)0.0370 (9)
H21A−0.03350.22591.31830.056*
H21B0.10440.28071.28520.056*
H21C−0.07060.25031.25750.056*
C22−0.2509 (4)0.3809 (3)1.32302 (14)0.0310 (8)
H22A−0.29940.45491.32430.037*
H22B−0.32000.33741.29760.037*
C23−0.2574 (5)0.3286 (4)1.37654 (16)0.0406 (9)
H23A−0.19830.37691.40230.049*
H23B−0.19660.25861.37630.049*
C24−0.4290 (5)0.3056 (4)1.39556 (15)0.0391 (9)
H24−0.48610.25701.36890.047*
C25−0.4156 (6)0.2408 (4)1.44664 (18)0.0487 (11)
H25A−0.33760.27871.47160.058*
H25B−0.52410.24061.46180.058*
C26−0.3607 (10)0.1263 (6)1.4410 (3)0.081 (2)
H26A−0.36550.08841.47450.122*
H26B−0.24770.12541.43030.122*
H26C−0.43260.08921.41460.122*
C27−0.5338 (5)0.4085 (5)1.39847 (17)0.0471 (11)
H27−0.53630.44381.36330.057*
C28−0.4660 (8)0.4907 (6)1.4369 (3)0.0713 (16)
H28A−0.52730.55931.43230.107*
H28B−0.35010.50381.43120.107*
H28C−0.47600.46311.47230.107*
C29−0.7116 (6)0.3790 (7)1.4087 (2)0.076 (2)
H29A−0.78200.44301.40200.114*
H29B−0.71730.35611.44510.114*
H29C−0.74910.31921.38550.114*
C300.0493 (4)0.6698 (3)0.97992 (12)0.0235 (7)
H300.16160.66290.99750.028*
C310.0640 (4)0.7452 (3)0.93332 (12)0.0224 (6)
H31A−0.04600.75650.91570.027*
H31B0.10600.81710.94570.027*
C320.1777 (3)0.6986 (3)0.89473 (11)0.0181 (6)
C330.1431 (3)0.5817 (3)0.87644 (11)0.0160 (6)
C34−0.0179 (4)0.5826 (3)0.84128 (12)0.0222 (6)
H34A−0.09940.62830.85730.033*
H34B−0.06000.50790.83730.033*
H34C0.00360.61230.80700.033*
C350.1201 (4)0.5101 (3)0.92521 (12)0.0209 (6)
H35A0.08270.43660.91360.025*
H35B0.22780.50150.94470.025*
C36−0.0024 (4)0.5562 (3)0.96208 (13)0.0255 (7)
H36A−0.11290.55920.94400.031*
H36B−0.00780.50760.99270.031*
C370.3035 (4)0.7581 (3)0.87996 (12)0.0199 (6)
H370.31740.82950.89410.024*
C380.4237 (3)0.7196 (3)0.84267 (12)0.0185 (6)
H380.44610.78030.81810.022*
C390.3607 (3)0.6209 (2)0.81143 (11)0.0153 (5)
H390.27130.64610.78590.018*
C400.2885 (3)0.5349 (2)0.84685 (11)0.0152 (6)
H400.37710.51620.87400.018*
C410.4956 (3)0.5704 (3)0.78089 (11)0.0175 (6)
H410.57980.54180.80740.021*
C420.4398 (4)0.4716 (3)0.74682 (11)0.0178 (6)
C430.3011 (4)0.5023 (3)0.70591 (12)0.0232 (6)
H43A0.34120.55720.68200.035*
H43B0.20810.53220.72350.035*
H43C0.26600.43700.68620.035*
C440.3826 (4)0.3852 (3)0.78485 (12)0.0206 (6)
H44A0.47670.36230.80850.025*
H44B0.34260.32010.76500.025*
C450.2451 (4)0.4284 (2)0.81739 (12)0.0198 (6)
H45A0.21800.37180.84290.024*
H45B0.14590.44100.79400.024*
C460.5878 (4)0.6436 (3)0.74431 (13)0.0255 (7)
H46A0.66950.68970.76410.031*
H46B0.51100.69140.72340.031*
C470.6719 (4)0.5619 (3)0.70931 (13)0.0250 (7)
H47A0.79200.56210.71760.030*
H47B0.65080.58200.67220.030*
C480.6003 (4)0.4470 (3)0.71962 (12)0.0205 (6)
H480.67730.40970.74570.025*
C490.5895 (4)0.3761 (3)0.66984 (12)0.0239 (7)
H490.51600.41450.64320.029*
C500.5169 (5)0.2628 (3)0.67837 (15)0.0329 (8)
H50A0.53040.21740.64750.049*
H50B0.40000.26980.68420.049*
H50C0.57390.22860.70890.049*
C510.7592 (4)0.3659 (3)0.64791 (13)0.0287 (7)
H51A0.82120.43420.65550.034*
H51B0.81970.30550.66610.034*
C520.7534 (5)0.3448 (4)0.58952 (15)0.0406 (10)
H52A0.67660.39770.57200.049*
H52B0.70840.27070.58270.049*
C530.9195 (5)0.3535 (4)0.56493 (15)0.0391 (9)
H530.89840.33810.52690.047*
C540.9931 (6)0.4687 (5)0.5694 (2)0.0570 (13)
H54A1.03900.47950.60570.068*
H54B1.08540.47320.54630.068*
C550.8742 (9)0.5623 (6)0.5556 (3)0.0802 (19)
H55A0.93020.63230.56190.120*
H55B0.78000.55750.57730.120*
H55C0.83600.55700.51870.120*
C561.0435 (5)0.2673 (4)0.58622 (16)0.0432 (10)
H561.06620.28190.62430.052*
C570.9728 (7)0.1508 (4)0.58050 (19)0.0544 (12)
H57A1.05480.09790.59410.082*
H57B0.94420.13560.54360.082*
H57C0.87430.14500.60020.082*
C581.2071 (6)0.2763 (5)0.5601 (2)0.0560 (13)
H58A1.25440.34900.56670.084*
H58B1.18790.26520.52240.084*
H58C1.28320.22050.57440.084*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0131 (10)0.0272 (12)0.0290 (11)−0.0035 (9)0.0025 (8)0.0003 (9)
O20.0222 (11)0.0439 (15)0.0234 (11)0.0218 (11)0.0041 (9)0.0031 (10)
O30.0111 (10)0.0516 (16)0.0254 (11)0.0018 (11)0.0026 (8)−0.0117 (11)
O40.0097 (9)0.0317 (13)0.0318 (11)−0.0049 (9)0.0049 (8)−0.0071 (10)
C10.0096 (13)0.0225 (16)0.0292 (15)0.0020 (12)0.0015 (11)−0.0021 (13)
C20.0234 (15)0.0126 (14)0.0305 (16)0.0035 (12)0.0007 (12)−0.0002 (12)
C30.0200 (14)0.0137 (14)0.0225 (14)0.0033 (11)−0.0006 (11)−0.0019 (11)
C40.0135 (13)0.0091 (13)0.0283 (15)0.0058 (10)−0.0006 (11)−0.0015 (11)
C50.0163 (14)0.0205 (16)0.0309 (16)0.0035 (12)−0.0031 (12)0.0014 (12)
C60.0143 (14)0.0124 (13)0.0328 (16)0.0034 (11)0.0036 (11)−0.0045 (12)
C70.0152 (13)0.0184 (15)0.0326 (16)0.0020 (12)0.0064 (11)−0.0045 (13)
C80.0292 (17)0.0153 (15)0.0245 (15)0.0075 (13)0.0019 (12)0.0018 (11)
C90.0264 (16)0.0141 (14)0.0236 (14)0.0114 (12)0.0024 (11)0.0014 (11)
C100.0187 (14)0.0133 (14)0.0212 (14)0.0065 (11)−0.0010 (11)−0.0013 (11)
C110.0143 (13)0.0130 (13)0.0253 (14)0.0040 (11)0.0024 (11)−0.0048 (11)
C120.0167 (14)0.0189 (15)0.0234 (14)0.0088 (12)0.0013 (11)−0.0026 (12)
C130.0144 (13)0.0166 (15)0.0269 (14)0.0000 (12)0.0019 (11)−0.0017 (12)
C140.0159 (14)0.0213 (16)0.0329 (16)0.0002 (12)−0.0003 (12)0.0035 (13)
C150.0223 (15)0.0120 (14)0.0368 (17)−0.0002 (12)0.0083 (13)−0.0036 (12)
C160.0213 (15)0.0101 (14)0.0381 (17)0.0046 (12)0.0101 (13)−0.0023 (12)
C170.0305 (17)0.0228 (17)0.0289 (16)0.0114 (14)0.0061 (13)−0.0008 (13)
C180.0268 (16)0.0286 (18)0.0288 (16)0.0105 (14)0.0067 (13)0.0002 (14)
C190.0158 (14)0.0237 (16)0.0295 (16)0.0000 (12)0.0033 (12)−0.0033 (13)
C200.0201 (15)0.0212 (16)0.0340 (17)−0.0039 (13)0.0064 (12)−0.0009 (13)
C210.037 (2)0.0208 (18)0.056 (2)−0.0044 (15)0.0200 (17)−0.0009 (16)
C220.0230 (16)0.036 (2)0.0348 (18)−0.0072 (15)0.0071 (13)−0.0037 (15)
C230.032 (2)0.049 (3)0.041 (2)−0.0006 (18)0.0103 (16)0.0056 (19)
C240.041 (2)0.047 (2)0.0302 (18)−0.0129 (19)0.0089 (15)−0.0036 (17)
C250.049 (3)0.052 (3)0.046 (2)−0.009 (2)0.0087 (19)0.006 (2)
C260.104 (5)0.067 (4)0.075 (4)0.018 (4)0.028 (4)0.010 (3)
C270.031 (2)0.068 (3)0.042 (2)0.004 (2)0.0075 (16)0.015 (2)
C280.077 (4)0.059 (4)0.078 (4)0.013 (3)0.011 (3)−0.007 (3)
C290.037 (3)0.125 (6)0.067 (3)0.003 (3)0.014 (2)0.041 (4)
C300.0089 (13)0.0367 (19)0.0254 (15)0.0018 (13)0.0035 (11)−0.0044 (13)
C310.0128 (13)0.0237 (16)0.0310 (15)0.0025 (12)0.0045 (11)−0.0070 (13)
C320.0110 (13)0.0177 (15)0.0256 (14)0.0021 (11)0.0014 (10)−0.0009 (12)
C330.0083 (12)0.0187 (14)0.0216 (13)−0.0023 (11)0.0049 (10)−0.0007 (11)
C340.0111 (13)0.0264 (16)0.0293 (15)−0.0025 (12)0.0028 (11)−0.0038 (13)
C350.0160 (14)0.0205 (16)0.0270 (15)−0.0044 (12)0.0073 (11)0.0012 (12)
C360.0175 (15)0.0321 (19)0.0279 (16)−0.0020 (13)0.0092 (12)0.0006 (13)
C370.0165 (14)0.0139 (14)0.0297 (15)−0.0013 (11)0.0041 (11)−0.0021 (12)
C380.0125 (13)0.0170 (15)0.0264 (14)−0.0039 (11)0.0037 (11)0.0011 (11)
C390.0099 (12)0.0136 (13)0.0230 (14)−0.0025 (10)0.0055 (10)0.0013 (11)
C400.0093 (12)0.0151 (14)0.0214 (13)−0.0025 (10)0.0040 (10)0.0010 (11)
C410.0112 (12)0.0198 (15)0.0221 (13)−0.0047 (11)0.0046 (10)0.0007 (11)
C420.0139 (13)0.0195 (15)0.0206 (13)−0.0003 (11)0.0057 (10)0.0013 (11)
C430.0158 (14)0.0285 (17)0.0253 (15)0.0012 (13)0.0021 (11)0.0004 (13)
C440.0188 (14)0.0170 (15)0.0266 (15)−0.0016 (12)0.0058 (11)0.0024 (12)
C450.0199 (14)0.0113 (14)0.0291 (15)−0.0043 (11)0.0085 (12)0.0006 (11)
C460.0214 (15)0.0267 (18)0.0295 (16)−0.0060 (13)0.0105 (12)0.0010 (13)
C470.0199 (15)0.0253 (17)0.0311 (16)−0.0034 (13)0.0106 (12)0.0017 (13)
C480.0145 (13)0.0229 (16)0.0246 (15)0.0005 (12)0.0044 (11)0.0013 (12)
C490.0225 (15)0.0270 (17)0.0229 (14)0.0042 (13)0.0072 (12)−0.0017 (13)
C500.039 (2)0.0231 (18)0.0377 (19)−0.0024 (15)0.0105 (15)−0.0058 (15)
C510.0243 (16)0.0340 (19)0.0287 (16)0.0080 (14)0.0087 (13)−0.0002 (14)
C520.0312 (19)0.059 (3)0.0323 (19)0.0000 (19)0.0087 (15)0.0003 (18)
C530.040 (2)0.048 (2)0.0308 (18)0.0008 (19)0.0120 (15)−0.0002 (17)
C540.048 (3)0.066 (3)0.059 (3)0.000 (2)0.015 (2)0.011 (3)
C550.086 (5)0.073 (4)0.082 (4)0.003 (4)0.008 (3)0.028 (4)
C560.045 (2)0.053 (3)0.0323 (19)0.005 (2)0.0090 (16)−0.0046 (18)
C570.064 (3)0.049 (3)0.053 (3)−0.005 (2)0.020 (2)−0.002 (2)
C580.040 (2)0.068 (3)0.062 (3)0.011 (2)0.018 (2)−0.001 (3)

Geometric parameters (Å, °)

O1—C11.436 (4)C28—H28C0.9800
O1—H1O0.8400C29—H29A0.9800
O2—C91.433 (4)C29—H29B0.9800
O2—H2O0.8400C29—H29C0.9800
O3—C301.421 (4)C30—C361.515 (5)
O3—H3O0.8400C30—C311.522 (5)
O4—C381.460 (4)C30—H301.0000
O4—H4O0.8400C31—C321.513 (4)
C1—C71.507 (5)C31—H31A0.9900
C1—C21.523 (4)C31—H31B0.9900
C1—H11.0000C32—C371.334 (4)
C2—C31.511 (4)C32—C331.526 (4)
C2—H2A0.9900C33—C341.548 (4)
C2—H2B0.9900C33—C351.550 (4)
C3—C81.340 (4)C33—C401.559 (4)
C3—C41.531 (4)C34—H34A0.9800
C4—C51.545 (4)C34—H34B0.9800
C4—C61.552 (4)C34—H34C0.9800
C4—C111.558 (4)C35—C361.529 (4)
C5—H5A0.9800C35—H35A0.9900
C5—H5B0.9800C35—H35B0.9900
C5—H5C0.9800C36—H36A0.9900
C6—C71.531 (4)C36—H36B0.9900
C6—H6A0.9900C37—C381.491 (4)
C6—H6B0.9900C37—H370.9500
C7—H7A0.9900C38—C391.522 (4)
C7—H7B0.9900C38—H381.0000
C8—C91.499 (5)C39—C411.524 (4)
C8—H80.9500C39—C401.533 (4)
C9—C101.531 (4)C39—H391.0000
C9—H91.0000C40—C451.537 (4)
C10—C121.517 (4)C40—H401.0000
C10—C111.531 (4)C41—C461.531 (4)
C10—H101.0000C41—C421.544 (4)
C11—C161.542 (4)C41—H411.0000
C11—H111.0000C42—C441.533 (4)
C12—C131.531 (4)C42—C431.542 (4)
C12—C171.531 (4)C42—C481.554 (4)
C12—H121.0000C43—H43A0.9800
C13—C151.540 (4)C43—H43B0.9800
C13—C141.543 (4)C43—H43C0.9800
C13—C191.564 (4)C44—C451.536 (4)
C14—H14A0.9800C44—H44A0.9900
C14—H14B0.9800C44—H44B0.9900
C14—H14C0.9800C45—H45A0.9900
C15—C161.531 (4)C45—H45B0.9900
C15—H15A0.9900C46—C471.537 (5)
C15—H15B0.9900C46—H46A0.9900
C16—H16A0.9900C46—H46B0.9900
C16—H16B0.9900C47—C481.552 (5)
C17—C181.544 (5)C47—H47A0.9900
C17—H17A0.9900C47—H47B0.9900
C17—H17B0.9900C48—C491.543 (4)
C18—C191.553 (5)C48—H481.0000
C18—H18A0.9900C49—C501.529 (5)
C18—H18B0.9900C49—C511.534 (4)
C19—C201.538 (5)C49—H491.0000
C19—H191.0000C50—H50A0.9800
C20—C221.536 (5)C50—H50B0.9800
C20—C211.538 (5)C50—H50C0.9800
C20—H201.0000C51—C521.520 (5)
C21—H21A0.9800C51—H51A0.9900
C21—H21B0.9800C51—H51B0.9900
C21—H21C0.9800C52—C531.536 (5)
C22—C231.521 (5)C52—H52A0.9900
C22—H22A0.9900C52—H52B0.9900
C22—H22B0.9900C53—C541.535 (7)
C23—C241.540 (6)C53—C561.538 (6)
C23—H23A0.9900C53—H531.0000
C23—H23B0.9900C54—C551.529 (9)
C24—C271.527 (7)C54—H54A0.9900
C24—C251.531 (6)C54—H54B0.9900
C24—H241.0000C55—H55A0.9800
C25—C261.481 (9)C55—H55B0.9800
C25—H25A0.9900C55—H55C0.9800
C25—H25B0.9900C56—C581.537 (6)
C26—H26A0.9800C56—C571.542 (7)
C26—H26B0.9800C56—H561.0000
C26—H26C0.9800C57—H57A0.9800
C27—C281.492 (8)C57—H57B0.9800
C27—C291.535 (6)C57—H57C0.9800
C27—H271.0000C58—H58A0.9800
C28—H28A0.9800C58—H58B0.9800
C28—H28B0.9800C58—H58C0.9800
C1—O1—H1O109.5H29A—C29—H29C109.5
C9—O2—H2O109.5H29B—C29—H29C109.5
C30—O3—H3O109.5O3—C30—C36113.9 (3)
C38—O4—H4O109.5O3—C30—C31111.4 (3)
O1—C1—C7112.9 (2)C36—C30—C31110.6 (3)
O1—C1—C2107.9 (3)O3—C30—H30106.8
C7—C1—C2110.1 (3)C36—C30—H30106.8
O1—C1—H1108.6C31—C30—H30106.8
C7—C1—H1108.6C32—C31—C30111.7 (3)
C2—C1—H1108.6C32—C31—H31A109.3
C3—C2—C1111.5 (3)C30—C31—H31A109.3
C3—C2—H2A109.3C32—C31—H31B109.3
C1—C2—H2A109.3C30—C31—H31B109.3
C3—C2—H2B109.3H31A—C31—H31B107.9
C1—C2—H2B109.3C37—C32—C31119.8 (3)
H2A—C2—H2B108.0C37—C32—C33123.7 (3)
C8—C3—C2120.4 (3)C31—C32—C33116.5 (3)
C8—C3—C4123.3 (3)C32—C33—C34107.9 (2)
C2—C3—C4116.3 (3)C32—C33—C35108.1 (2)
C3—C4—C5108.1 (2)C34—C33—C35109.5 (2)
C3—C4—C6108.6 (2)C32—C33—C40111.2 (2)
C5—C4—C6109.8 (2)C34—C33—C40111.3 (2)
C3—C4—C11109.4 (2)C35—C33—C40108.8 (2)
C5—C4—C11112.3 (2)C33—C34—H34A109.5
C6—C4—C11108.7 (2)C33—C34—H34B109.5
C4—C5—H5A109.5H34A—C34—H34B109.5
C4—C5—H5B109.5C33—C34—H34C109.5
H5A—C5—H5B109.5H34A—C34—H34C109.5
C4—C5—H5C109.5H34B—C34—H34C109.5
H5A—C5—H5C109.5C36—C35—C33114.2 (3)
H5B—C5—H5C109.5C36—C35—H35A108.7
C7—C6—C4114.2 (3)C33—C35—H35A108.7
C7—C6—H6A108.7C36—C35—H35B108.7
C4—C6—H6A108.7C33—C35—H35B108.7
C7—C6—H6B108.7H35A—C35—H35B107.6
C4—C6—H6B108.7C30—C36—C35110.2 (3)
H6A—C6—H6B107.6C30—C36—H36A109.6
C1—C7—C6111.0 (3)C35—C36—H36A109.6
C1—C7—H7A109.4C30—C36—H36B109.6
C6—C7—H7A109.4C35—C36—H36B109.6
C1—C7—H7B109.4H36A—C36—H36B108.1
C6—C7—H7B109.4C32—C37—C38124.1 (3)
H7A—C7—H7B108.0C32—C37—H37117.9
C3—C8—C9124.9 (3)C38—C37—H37117.9
C3—C8—H8117.5O4—C38—C37106.1 (2)
C9—C8—H8117.5O4—C38—C39111.6 (2)
O2—C9—C8111.1 (2)C37—C38—C39112.0 (2)
O2—C9—C10111.9 (3)O4—C38—H38109.0
C8—C9—C10111.6 (3)C37—C38—H38109.0
O2—C9—H9107.3C39—C38—H38109.0
C8—C9—H9107.3C38—C39—C41111.2 (2)
C10—C9—H9107.3C38—C39—C40111.2 (2)
C12—C10—C11110.6 (2)C41—C39—C40110.2 (2)
C12—C10—C9110.8 (2)C38—C39—H39108.0
C11—C10—C9110.1 (2)C41—C39—H39108.0
C12—C10—H10108.4C40—C39—H39108.0
C11—C10—H10108.4C39—C40—C45112.0 (2)
C9—C10—H10108.4C39—C40—C33111.8 (2)
C10—C11—C16112.2 (2)C45—C40—C33113.1 (2)
C10—C11—C4112.1 (2)C39—C40—H40106.5
C16—C11—C4112.7 (2)C45—C40—H40106.5
C10—C11—H11106.4C33—C40—H40106.5
C16—C11—H11106.4C39—C41—C46118.6 (3)
C4—C11—H11106.4C39—C41—C42114.4 (2)
C10—C12—C13115.0 (2)C46—C41—C42104.4 (2)
C10—C12—C17117.8 (3)C39—C41—H41106.2
C13—C12—C17104.6 (2)C46—C41—H41106.2
C10—C12—H12106.2C42—C41—H41106.2
C13—C12—H12106.2C44—C42—C43111.2 (2)
C17—C12—H12106.2C44—C42—C41105.6 (2)
C12—C13—C15105.7 (2)C43—C42—C41112.0 (3)
C12—C13—C14112.1 (3)C44—C42—C48116.9 (3)
C15—C13—C14111.1 (3)C43—C42—C48110.2 (2)
C12—C13—C19100.7 (2)C41—C42—C48100.4 (2)
C15—C13—C19116.7 (3)C42—C43—H43A109.5
C14—C13—C19110.0 (2)C42—C43—H43B109.5
C13—C14—H14A109.5H43A—C43—H43B109.5
C13—C14—H14B109.5C42—C43—H43C109.5
H14A—C14—H14B109.5H43A—C43—H43C109.5
C13—C14—H14C109.5H43B—C43—H43C109.5
H14A—C14—H14C109.5C42—C44—C45111.9 (3)
H14B—C14—H14C109.5C42—C44—H44A109.2
C16—C15—C13111.0 (3)C45—C44—H44A109.2
C16—C15—H15A109.4C42—C44—H44B109.2
C13—C15—H15A109.4C45—C44—H44B109.2
C16—C15—H15B109.4H44A—C44—H44B107.9
C13—C15—H15B109.4C44—C45—C40114.0 (2)
H15A—C15—H15B108.0C44—C45—H45A108.8
C15—C16—C11114.5 (3)C40—C45—H45A108.8
C15—C16—H16A108.6C44—C45—H45B108.8
C11—C16—H16A108.6C40—C45—H45B108.8
C15—C16—H16B108.6H45A—C45—H45B107.7
C11—C16—H16B108.6C41—C46—C47103.5 (3)
H16A—C16—H16B107.6C41—C46—H46A111.1
C12—C17—C18103.1 (3)C47—C46—H46A111.1
C12—C17—H17A111.1C41—C46—H46B111.1
C18—C17—H17A111.1C47—C46—H46B111.1
C12—C17—H17B111.1H46A—C46—H46B109.0
C18—C17—H17B111.1C46—C47—C48107.6 (2)
H17A—C17—H17B109.1C46—C47—H47A110.2
C17—C18—C19107.6 (3)C48—C47—H47A110.2
C17—C18—H18A110.2C46—C47—H47B110.2
C19—C18—H18A110.2C48—C47—H47B110.2
C17—C18—H18B110.2H47A—C47—H47B108.5
C19—C18—H18B110.2C49—C48—C47111.7 (3)
H18A—C18—H18B108.5C49—C48—C42118.5 (3)
C20—C19—C18111.8 (3)C47—C48—C42103.8 (3)
C20—C19—C13118.7 (3)C49—C48—H48107.4
C18—C19—C13103.7 (3)C47—C48—H48107.4
C20—C19—H19107.4C42—C48—H48107.4
C18—C19—H19107.4C50—C49—C51110.3 (3)
C13—C19—H19107.4C50—C49—C48113.1 (3)
C22—C20—C21109.8 (3)C51—C49—C48110.2 (3)
C22—C20—C19111.0 (3)C50—C49—H49107.7
C21—C20—C19112.8 (3)C51—C49—H49107.7
C22—C20—H20107.7C48—C49—H49107.7
C21—C20—H20107.7C49—C50—H50A109.5
C19—C20—H20107.7C49—C50—H50B109.5
C20—C21—H21A109.5H50A—C50—H50B109.5
C20—C21—H21B109.5C49—C50—H50C109.5
H21A—C21—H21B109.5H50A—C50—H50C109.5
C20—C21—H21C109.5H50B—C50—H50C109.5
H21A—C21—H21C109.5C52—C51—C49113.8 (3)
H21B—C21—H21C109.5C52—C51—H51A108.8
C23—C22—C20114.9 (3)C49—C51—H51A108.8
C23—C22—H22A108.6C52—C51—H51B108.8
C20—C22—H22A108.6C49—C51—H51B108.8
C23—C22—H22B108.6H51A—C51—H51B107.7
C20—C22—H22B108.6C51—C52—C53114.9 (3)
H22A—C22—H22B107.5C51—C52—H52A108.5
C22—C23—C24116.7 (3)C53—C52—H52A108.5
C22—C23—H23A108.1C51—C52—H52B108.5
C24—C23—H23A108.1C53—C52—H52B108.5
C22—C23—H23B108.1H52A—C52—H52B107.5
C24—C23—H23B108.1C54—C53—C52112.6 (4)
H23A—C23—H23B107.3C54—C53—C56110.9 (4)
C27—C24—C25113.3 (3)C52—C53—C56112.7 (4)
C27—C24—C23112.9 (4)C54—C53—H53106.7
C25—C24—C23110.5 (4)C52—C53—H53106.7
C27—C24—H24106.6C56—C53—H53106.7
C25—C24—H24106.6C55—C54—C53115.5 (5)
C23—C24—H24106.6C55—C54—H54A108.4
C26—C25—C24114.3 (4)C53—C54—H54A108.4
C26—C25—H25A108.7C55—C54—H54B108.4
C24—C25—H25A108.7C53—C54—H54B108.4
C26—C25—H25B108.7H54A—C54—H54B107.5
C24—C25—H25B108.7C54—C55—H55A109.5
H25A—C25—H25B107.6C54—C55—H55B109.5
C25—C26—H26A109.5H55A—C55—H55B109.5
C25—C26—H26B109.5C54—C55—H55C109.5
H26A—C26—H26B109.5H55A—C55—H55C109.5
C25—C26—H26C109.5H55B—C55—H55C109.5
H26A—C26—H26C109.5C58—C56—C53111.5 (4)
H26B—C26—H26C109.5C58—C56—C57110.8 (4)
C28—C27—C24113.8 (4)C53—C56—C57111.4 (4)
C28—C27—C29111.1 (5)C58—C56—H56107.6
C24—C27—C29110.8 (5)C53—C56—H56107.6
C28—C27—H27106.9C57—C56—H56107.6
C24—C27—H27106.9C56—C57—H57A109.5
C29—C27—H27106.9C56—C57—H57B109.5
C27—C28—H28A109.5H57A—C57—H57B109.5
C27—C28—H28B109.5C56—C57—H57C109.5
H28A—C28—H28B109.5H57A—C57—H57C109.5
C27—C28—H28C109.5H57B—C57—H57C109.5
H28A—C28—H28C109.5C56—C58—H58A109.5
H28B—C28—H28C109.5C56—C58—H58B109.5
C27—C29—H29A109.5H58A—C58—H58B109.5
C27—C29—H29B109.5C56—C58—H58C109.5
H29A—C29—H29B109.5H58A—C58—H58C109.5
C27—C29—H29C109.5H58B—C58—H58C109.5
O1—C1—C2—C3−179.6 (2)O3—C30—C31—C32177.6 (2)
C7—C1—C2—C3−56.0 (3)C36—C30—C31—C32−54.6 (3)
C1—C2—C3—C8−127.2 (3)C30—C31—C32—C37−125.8 (3)
C1—C2—C3—C452.8 (3)C30—C31—C32—C3352.0 (3)
C8—C3—C4—C5−108.6 (3)C37—C32—C33—C34−112.4 (3)
C2—C3—C4—C571.4 (3)C31—C32—C33—C3470.0 (3)
C8—C3—C4—C6132.3 (3)C37—C32—C33—C35129.4 (3)
C2—C3—C4—C6−47.6 (3)C31—C32—C33—C35−48.3 (3)
C8—C3—C4—C1113.9 (4)C37—C32—C33—C4010.0 (4)
C2—C3—C4—C11−166.0 (2)C31—C32—C33—C40−167.7 (2)
C3—C4—C6—C748.7 (3)C32—C33—C35—C3650.8 (3)
C5—C4—C6—C7−69.2 (3)C34—C33—C35—C36−66.4 (3)
C11—C4—C6—C7167.6 (2)C40—C33—C35—C36171.7 (2)
O1—C1—C7—C6178.6 (2)O3—C30—C36—C35−176.2 (3)
C2—C1—C7—C657.9 (3)C31—C30—C36—C3557.4 (3)
C4—C6—C7—C1−56.2 (3)C33—C35—C36—C30−57.4 (3)
C2—C3—C8—C9−178.1 (3)C31—C32—C37—C38179.3 (3)
C4—C3—C8—C92.0 (5)C33—C32—C37—C381.7 (5)
C3—C8—C9—O2−111.9 (3)C32—C37—C38—O4−105.2 (3)
C3—C8—C9—C1013.7 (4)C32—C37—C38—C3916.8 (4)
O2—C9—C10—C12−42.1 (3)O4—C38—C39—C41−51.0 (3)
C8—C9—C10—C12−167.3 (3)C37—C38—C39—C41−169.8 (2)
O2—C9—C10—C1180.6 (3)O4—C38—C39—C4072.2 (3)
C8—C9—C10—C11−44.6 (3)C37—C38—C39—C40−46.5 (3)
C12—C10—C11—C16−46.3 (3)C38—C39—C40—C45−172.5 (2)
C9—C10—C11—C16−169.1 (3)C41—C39—C40—C45−48.6 (3)
C12—C10—C11—C4−174.3 (2)C38—C39—C40—C3359.4 (3)
C9—C10—C11—C462.9 (3)C41—C39—C40—C33−176.7 (2)
C3—C4—C11—C10−45.6 (3)C32—C33—C40—C39−39.8 (3)
C5—C4—C11—C1074.3 (3)C34—C33—C40—C3980.6 (3)
C6—C4—C11—C10−164.0 (2)C35—C33—C40—C39−158.7 (2)
C3—C4—C11—C16−173.3 (2)C32—C33—C40—C45−167.3 (2)
C5—C4—C11—C16−53.4 (3)C34—C33—C40—C45−47.0 (3)
C6—C4—C11—C1668.3 (3)C35—C33—C40—C4573.8 (3)
C11—C10—C12—C1356.7 (3)C38—C39—C41—C46−54.3 (3)
C9—C10—C12—C13179.1 (2)C40—C39—C41—C46−178.1 (3)
C11—C10—C12—C17−179.2 (3)C38—C39—C41—C42−178.2 (2)
C9—C10—C12—C17−56.9 (3)C40—C39—C41—C4258.0 (3)
C10—C12—C13—C15−61.8 (3)C39—C41—C42—C44−61.4 (3)
C17—C12—C13—C15167.4 (3)C46—C41—C42—C44167.4 (2)
C10—C12—C13—C1459.3 (3)C39—C41—C42—C4359.7 (3)
C17—C12—C13—C14−71.4 (3)C46—C41—C42—C43−71.5 (3)
C10—C12—C13—C19176.3 (2)C39—C41—C42—C48176.6 (2)
C17—C12—C13—C1945.6 (3)C46—C41—C42—C4845.4 (3)
C12—C13—C15—C1658.3 (3)C43—C42—C44—C45−64.1 (3)
C14—C13—C15—C16−63.5 (3)C41—C42—C44—C4557.6 (3)
C19—C13—C15—C16169.3 (3)C48—C42—C44—C45168.2 (3)
C13—C15—C16—C11−54.6 (4)C42—C44—C45—C40−54.5 (3)
C10—C11—C16—C1547.4 (4)C39—C40—C45—C4448.5 (3)
C4—C11—C16—C15175.1 (3)C33—C40—C45—C44176.0 (2)
C10—C12—C17—C18−165.3 (3)C39—C41—C46—C47−163.5 (3)
C13—C12—C17—C18−36.2 (3)C42—C41—C46—C47−34.9 (3)
C12—C17—C18—C1912.4 (3)C41—C46—C47—C4810.5 (3)
C17—C18—C19—C20144.2 (3)C46—C47—C48—C49146.1 (3)
C17—C18—C19—C1315.1 (3)C46—C47—C48—C4217.3 (3)
C12—C13—C19—C20−161.2 (3)C44—C42—C48—C4984.2 (3)
C15—C13—C19—C2085.0 (4)C43—C42—C48—C49−44.0 (4)
C14—C13—C19—C20−42.7 (4)C41—C42—C48—C49−162.2 (3)
C12—C13—C19—C18−36.5 (3)C44—C42—C48—C47−151.3 (3)
C15—C13—C19—C18−150.3 (3)C43—C42—C48—C4780.5 (3)
C14—C13—C19—C1882.0 (3)C41—C42—C48—C47−37.7 (3)
C18—C19—C20—C2259.9 (4)C47—C48—C49—C50−179.1 (3)
C13—C19—C20—C22−179.5 (3)C42—C48—C49—C50−58.5 (4)
C18—C19—C20—C21−176.4 (3)C47—C48—C49—C5156.9 (3)
C13—C19—C20—C21−55.7 (4)C42—C48—C49—C51177.5 (3)
C21—C20—C22—C2370.0 (4)C50—C49—C51—C5280.5 (4)
C19—C20—C22—C23−164.7 (3)C48—C49—C51—C52−153.8 (3)
C20—C22—C23—C24−173.5 (3)C49—C51—C52—C53170.2 (4)
C22—C23—C24—C27−58.9 (5)C51—C52—C53—C54−63.0 (5)
C22—C23—C24—C25173.2 (4)C51—C52—C53—C5663.3 (5)
C27—C24—C25—C26162.0 (5)C52—C53—C54—C55−45.6 (6)
C23—C24—C25—C26−70.2 (6)C56—C53—C54—C55−172.9 (4)
C25—C24—C27—C2863.1 (5)C54—C53—C56—C58−54.0 (5)
C23—C24—C27—C28−63.4 (5)C52—C53—C56—C58178.7 (4)
C25—C24—C27—C29−62.9 (5)C54—C53—C56—C57−178.4 (4)
C23—C24—C27—C29170.6 (4)C52—C53—C56—C5754.3 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O···O40.841.922.762 (3)178
O2—H2O···O30.841.872.686 (3)165
O3—H3O···O1i0.841.862.694 (3)170

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2810).

References

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