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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Pages o1160-o1161

17-Deoxoestrone [estra-1,3,5(10)-trien-3-ol]–methanol (3/1)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 11 April 2011; accepted 11 April 2011; online 16 April 2011)

Three independent mol­ecules of the title estrone derivative and a mol­ecule of methanol comprise the asymmetric unit of the title compound [systematic name: 13-methyl-6,7,8,9,11,12,13,14,15,16-deca­hydro­cyclo­penta­[a]phenanthren-3-ol–meth­an­ol (3/1)], 3C18H24O·CH3OH. Two of the estrone mol­ecules exhibit 50:50 disorder (one displays whole-mol­ecule disorder and the other partial disorder in the fused five- and six-membered rings) so that five (partial) mol­ecular conformations are discernable. The conformation of the six-membered ring abutting the aromatic ring is close to a half-chair in all five components. The conformation of the six-membered ring fused to the five-membered ring is based on a chair with varying degrees of distortion ranging from minor to significant. Two distinct conformations are found for the five-membered ring: in four mol­ecules, the five-membered ring is twisted about the bond linking it to the six-membered ring, and in the other, the five-membered ring is an envelope with the quaternary C atom being the flap atom. The crystal packing features O—H⋯O hydrogen bonding whereby the four mol­ecules comprising the asymmetric unit are linked into a supra­molecular chain along the b axis.

Related literature

For the original synthesis, see: Huang-Minlon (1949[Huang-Minlon (1949). J. Am. Chem. Soc. 71, 3301-3303.]). For geometric and structural features for a series of cholestane derivatives, see: Rajnikant et al. (2006[Rajnikant, Dinesh, & Bhavnaish, C. (2006). Acta Cryst. A62, 136-145.]). For background to steroidal estrogen boronic acids and boronates, see: Ketuly & Hadi (2010[Ketuly, K. A. & Hadi, A. H. (2010). Molecules, 15, 2347-2356.]). For related structures see: Ketuly et al. (1997[Ketuly, K. A., Yufit, D. S., Brooks, C. J. W. & Freer, A. A. (1997). Acta Cryst. C53, 981-982.], 2010[Ketuly, K. A., Hadi, A. H. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2265.]).

[Scheme 1]

Experimental

Crystal data
  • 3C18H24O·CH4O

  • Mr = 801.16

  • Monoclinic, C 2

  • a = 24.3084 (16) Å

  • b = 7.7235 (5) Å

  • c = 26.6479 (18) Å

  • β = 114.292 (1)°

  • V = 4560.1 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.35 × 0.20 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.976, Tmax = 0.993

  • 21707 measured reflections

  • 5612 independent reflections

  • 4481 reflections with I > 2σ(I)

  • Rint = 0.050

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.141

  • S = 1.02

  • 5612 reflections

  • 616 parameters

  • 234 restraints

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O3 0.84 1.83 2.662 (3) 170
O2—H2⋯O4 0.84 1.82 2.655 (4) 170
O3—H3⋯O2 0.84 1.88 2.711 (3) 173
O4—H4⋯O1i 0.84 1.90 2.736 (4) 178
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]), DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and QMOL (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The title estrone, (I), has been prepared by a modified procedure from Huang-Minlon (1949) as a precursor for the synthesis of steroidal estrogen boronic acids and boronates (Ketuly & Hadi, 2010). Related structures have been reported (Ketuly et al., 1997; Ketuly et al., 2010) as has a systematic evaluation of geometric and structural features for a series of cholestane derivatives (Rajnikant et al., 2006). Herein, the crystal and molecular structure of (I) is described.

Three independent estrone molecules, Figs 1 - 3, and a solvent methanol molecule comprise the asymmetric unit of (I). The first independent molecule exhibits whole molecule disorder pivoted on the O1 atom. As seen from the overlay diagram, Fig. 4, the two components of equal weight, i.e. shown as red and green, have almost identical conformations. Referring to the Scheme for numbering of the rings, the six-membered ring B, being fused to an aromatic ring, has an half-chair conformation, six-membered ring C has a slightly twisted chair conformation, and five-membered ring C is twisted on the bond linking it to the six-membered ring. Disorder is also evident in the second independent molecule. In this case, the 50:50 disorder is restricted to rings C and D. As shown in pink and blue in Fig. 4, the rings have distinct conformations. For the molecule illustrated in pink, ring B is an half-chair and the conformation of ring C is that of a twisted chair. Ring D is an envelope on the quaternary-C29 atom. In the second disordered conformation, ring B is an half-chair and ring C is a slightly twisted chair. Ring D is distinct from that in the first orientation in that is adopts a twisted conformation about the C25—C29 bond. The third independent molecule, shown as light-blue in Fig. 4, is different from the other molecules in that ring B is a slightly twisted half-chair, ring C is a slightly twisted chair, and ring C is twisted about the C43—C47 bond.

In the crystal packing, the four independent molecules are connected via a sequence of O—H···O hydrogen bonds, Table 1. These link molecules into a supramolecular chain along the b axis, Fig. 5.

Related literature top

For the original synthesis, see: Huang-Minlon (1949). For geometric and structural features for a series of cholestane derivatives, see: Rajnikant et al. (2006). For background to steroidal estrogen boronic acids and boronates, see: Ketuly & Hadi (2010). For related structures see: Ketuly et al. (1997, 2010).

Experimental top

The title compound (I) was prepared by a modified procedure from Huang-Minlon (1949) Estrone (1.5 g) was dissolved in diethylene glycol (40 ml), with heating and stirring in an oil bath at 388–393 K. Hydrazine hydrate (98–100%) was added in four 3 ml portions at 15 min intervals. During this time stirring and heating was continued and the flask connected to a drying tube. While the temperature was raised to 423 K, nitrogen was bubbled through the reaction mixture to remove excess reagent and water as by-product. When most of the reagent had been evaporated, KOH pellets (9.6 g) were added. The flask was then fitted with a 50 cm air condenser (with a drying tube), and the reaction mixture was refluxed for 2 h under nitrogen. The cooled basic reaction mixture was diluted with water and extracted three times with ether, and each extract was washed five times with water. The ether extracts were dried under vacuum and the residue crystallized from MeOH/water, yielding colourless crystals (1.305 g, 91%), M.pt. 401–403 K. This product was recrystallized three times from MeOH/water, yielding (I). M.pt. 407–408 K, (Lit. 407–407.5 K (Huang-Minlon, 1949)).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Ueq(C). The hydroxy H-atoms were similarly placed (O—H 0.84 Å) and their Uiso(H) similarly tied. Of the three independent molecules, one (with O1) is whole-molecule disordered and another (with O2) is partially disordered. The disorder was assumed to be a 1:1 disorder as the occupancy could not be refined. The aromatic C–C distances were restrained to 1.39±0.01 Å and the aliphatic ones to 1.54±0.01 Å; for the aliphatic arbon atoms, the 1,3-related distances were restrained to 2.52±0.01 Å. The anisotropic displacement factors of the primed atoms were restrained to be equal to those of the unprimed ones, and the anisotropic displacement factors of the disordered carbon atoms were restrained to be nearly isotropic. In the absence of significant anomalous scattering effects, 2199 Friedel pairs were averaged in the final refinement. However, the absolute configuration was assigned on the basis of the known chirality of the estrone starting material.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMOL (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structures of the first independent molecule comprising the asymmetric unit of (I) showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. The molecular structures of the second independent molecule comprising the asymmetric unit of (I) showing displacement ellipsoids at the 50% probability level.
[Figure 3] Fig. 3. The molecular structures of the third independent molecule comprising the asymmetric unit of (I) showing displacement ellipsoids at the 50% probability level.
[Figure 4] Fig. 4. Overlay diagram the three independent molecules comprising the asymmetric unit of (I) and their disordered components. The disordered components of the molecule shown in Fig. 1 are shown in red and green, the disordered components of Fig. 2 are shown in blue and pink, and the molecule in Fig. 3 is shown in light-blue.
[Figure 5] Fig. 5. View of the supramolecular chain aligned along the b axis of the crystal structure of (I). The O—H···O contacts hydrogen bonds are shown as orange dashed lines. Only one orientation of the disordered O—H1 atom is shown.
13-methyl-6,7,8,9,11,12,13,14,15,16- decahydrocyclopenta[a]phenanthren-3-ol–methanol (3/1) top
Crystal data top
3C18H24O·CH4OF(000) = 1752
Mr = 801.16Dx = 1.167 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 5587 reflections
a = 24.3084 (16) Åθ = 2.3–28.2°
b = 7.7235 (5) ŵ = 0.07 mm1
c = 26.6479 (18) ÅT = 100 K
β = 114.292 (1)°Block, colourless
V = 4560.1 (5) Å30.35 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
5612 independent reflections
Radiation source: fine-focus tube4481 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.050
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3131
Tmin = 0.976, Tmax = 0.993k = 1010
21707 measured reflectionsl = 3434
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.141 w = 1/[σ2(Fo2) + (0.0693P)2 + 3.2841P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5612 reflectionsΔρmax = 0.37 e Å3
616 parametersΔρmin = 0.33 e Å3
234 restraintsAbsolute structure: 2199 Friedel pairs were merged
Primary atom site location: structure-invariant direct methods
Crystal data top
3C18H24O·CH4OV = 4560.1 (5) Å3
Mr = 801.16Z = 4
Monoclinic, C2Mo Kα radiation
a = 24.3084 (16) ŵ = 0.07 mm1
b = 7.7235 (5) ÅT = 100 K
c = 26.6479 (18) Å0.35 × 0.20 × 0.10 mm
β = 114.292 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer
5612 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4481 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.993Rint = 0.050
21707 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.052234 restraints
wR(F2) = 0.141H-atom parameters constrained
S = 1.02Δρmax = 0.37 e Å3
5612 reflectionsΔρmin = 0.33 e Å3
616 parametersAbsolute structure: 2199 Friedel pairs were merged
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.53469 (10)1.0006 (3)0.20950 (10)0.0371 (6)
H10.52040.90200.19820.056*0.50
H1'0.52120.89910.20570.056*0.50
O20.57490 (9)0.4963 (3)0.14534 (10)0.0321 (5)
H20.57010.39110.13660.048*
O30.50222 (10)0.6730 (3)0.18194 (10)0.0351 (6)
H30.52350.61060.17110.053*
O40.55238 (11)0.1609 (4)0.12576 (11)0.0421 (6)
H40.54660.11340.15150.063*
C10.5807 (19)1.0199 (18)0.2620 (12)0.0308 (17)0.50
C20.6019 (7)1.1867 (17)0.2777 (4)0.0258 (19)0.50
H2A0.58251.27970.25350.031*0.50
C30.6503 (4)1.2235 (10)0.3273 (3)0.0243 (15)0.50
C40.6678 (3)1.4130 (9)0.3394 (3)0.0302 (12)0.50
H4A0.63211.47990.33720.036*0.50
H4B0.68031.45860.31100.036*0.50
C50.7192 (3)1.4396 (9)0.3963 (3)0.0347 (11)0.50
H5A0.73921.55180.39700.042*0.50
H5B0.70231.44410.42440.042*0.50
C60.7658 (3)1.2950 (8)0.4109 (3)0.0271 (10)0.50
H60.77981.28340.38060.032*0.50
C70.8204 (3)1.3310 (9)0.4649 (3)0.0346 (11)0.50
H70.80481.33260.49420.041*0.50
C80.8559 (4)1.4986 (10)0.4715 (3)0.0503 (15)0.50
H8A0.83491.59730.47960.060*0.50
H8B0.86221.52470.43780.060*0.50
C90.9164 (5)1.4603 (12)0.5206 (4)0.066 (2)0.50
H9A0.92041.53140.55280.079*0.50
H9B0.95071.48660.51090.079*0.50
C100.9153 (4)1.2642 (10)0.5336 (3)0.0495 (15)0.50
H10A0.95531.21080.54280.059*0.50
H10B0.90401.24690.56490.059*0.50
C110.8676 (3)1.1855 (9)0.4805 (2)0.0324 (11)0.50
C120.8956 (4)1.1604 (13)0.4388 (3)0.0412 (16)0.50
H12A0.92361.06230.45020.062*0.50
H12B0.91751.26560.43740.062*0.50
H12C0.86361.13750.40230.062*0.50
C130.8376 (3)1.0165 (10)0.4873 (3)0.0391 (12)0.50
H13A0.82661.02780.51910.047*0.50
H13B0.86660.91970.49500.047*0.50
C140.7801 (3)0.9748 (9)0.4348 (3)0.0332 (11)0.50
H14A0.79230.94340.40470.040*0.50
H14B0.75980.87310.44210.040*0.50
C150.7352 (3)1.1254 (8)0.4155 (3)0.0291 (10)0.50
H150.71991.14370.44460.035*0.50
C160.6799 (3)1.0863 (8)0.3618 (3)0.0252 (12)0.50
C170.6585 (4)0.9186 (9)0.3464 (4)0.0316 (14)0.50
H170.67730.82560.37080.038*0.50
C180.6104 (6)0.8834 (16)0.2964 (5)0.032 (2)0.50
H18A0.59800.76740.28590.038*0.50
C1'0.5807 (19)1.051 (2)0.2582 (12)0.0308 (17)0.50
C2'0.5974 (7)1.2241 (16)0.2647 (5)0.0258 (19)0.50
H2'0.57771.30460.23590.031*0.50
C3'0.6434 (4)1.2783 (9)0.3139 (3)0.0243 (15)0.50
C4'0.6605 (3)1.4689 (9)0.3177 (3)0.0302 (12)0.50
H4'A0.62361.53970.30800.036*0.50
H4'B0.67721.49360.29020.036*0.50
C5'0.7070 (3)1.5246 (9)0.3748 (3)0.0347 (11)0.50
H5'A0.72731.63230.37140.042*0.50
H5'B0.68621.54840.39920.042*0.50
C6'0.7538 (3)1.3821 (8)0.3999 (2)0.0271 (10)0.50
H6'0.77121.35060.37310.032*0.50
C7'0.8054 (3)1.4399 (9)0.4540 (2)0.0346 (11)0.50
H7'0.78701.46280.48070.041*0.50
C8'0.8418 (4)1.6017 (11)0.4538 (3)0.0503 (15)0.50
H8'A0.81911.70860.45340.060*0.50
H8'B0.85231.60220.42170.060*0.50
C9'0.8987 (5)1.5852 (12)0.5081 (3)0.066 (2)0.50
H9'10.93551.60330.50140.079*0.50
H9'20.89811.67240.53510.079*0.50
C10'0.8980 (4)1.4011 (11)0.5298 (3)0.0495 (15)0.50
H10C0.88411.40270.55990.059*0.50
H10D0.93871.34870.54370.059*0.50
C11'0.8534 (3)1.2992 (9)0.4799 (3)0.0324 (11)0.50
C12'0.8849 (4)1.2449 (12)0.4428 (4)0.0412 (16)0.50
H12D0.91431.15340.46100.062*0.50
H12E0.90571.34500.43600.062*0.50
H12F0.85481.20150.40770.062*0.50
C13'0.8224 (3)1.1431 (9)0.4919 (3)0.0391 (12)0.50
H13C0.80761.17520.52010.047*0.50
H13D0.85211.04850.50710.047*0.50
C14'0.7688 (3)1.0772 (9)0.4399 (3)0.0332 (11)0.50
H14C0.78441.02820.41400.040*0.50
H14D0.74790.98340.45040.040*0.50
C15'0.7235 (3)1.2217 (8)0.4109 (3)0.0291 (10)0.50
H15'0.70471.25770.43640.035*0.50
C16'0.6717 (3)1.1612 (9)0.3566 (3)0.0252 (12)0.50
C17'0.6509 (4)0.9919 (9)0.3498 (4)0.0316 (14)0.50
H17'0.66890.91270.37930.038*0.50
C18'0.6048 (6)0.9332 (16)0.3013 (5)0.032 (2)0.50
H18'0.59030.81750.29780.038*0.50
C190.63506 (13)0.5273 (5)0.17821 (14)0.0312 (7)
C200.65239 (13)0.6954 (4)0.19521 (13)0.0263 (7)
H200.62330.78560.18250.032*
C210.71149 (14)0.7350 (4)0.23044 (13)0.0265 (7)
C220.72835 (14)0.9220 (5)0.24470 (14)0.0298 (7)
H22A0.70000.97330.25870.036*
H22B0.72310.98480.21060.036*
C230.79207 (15)0.9501 (5)0.28701 (16)0.0417 (9)
H23A0.79250.94210.32430.050*
H23B0.80511.06840.28260.050*
C240.83713 (12)0.8193 (5)0.28247 (13)0.0291 (7)
H240.83660.82490.24480.035*0.50
H24'0.83410.82330.24390.035*0.50
C250.9010 (3)0.8549 (10)0.3256 (5)0.0329 (9)0.50
H250.90310.86680.36370.039*0.50
C260.9332 (3)1.0042 (10)0.3095 (3)0.0375 (16)0.50
H26A0.92361.11660.32190.045*0.50
H26B0.91971.00820.26910.045*0.50
C271.0029 (3)0.9685 (11)0.3383 (4)0.0450 (17)0.50
H27A1.02351.05540.36730.054*0.50
H27B1.02120.97000.31130.054*0.50
C281.0068 (6)0.7803 (13)0.3641 (5)0.0421 (13)0.50
H28A1.00850.78460.40190.051*0.50
H28B1.04140.71300.36410.051*0.50
C290.9437 (3)0.7076 (11)0.3205 (4)0.0427 (12)0.50
C300.9483 (3)0.7570 (11)0.2639 (3)0.0380 (14)0.50
H30A0.97500.67480.25690.057*0.50
H30B0.96450.87440.26660.057*0.50
H30C0.90800.75190.23360.057*0.50
C310.9289 (4)0.5501 (11)0.3333 (5)0.0707 (16)0.50
H31A0.94400.54440.37390.085*0.50
H31B0.95170.46280.32230.085*0.50
C320.8617 (3)0.4922 (9)0.3089 (4)0.0390 (17)0.50
H32A0.85380.41860.27620.047*0.50
H32B0.85460.42100.33650.047*0.50
C330.81816 (14)0.6413 (5)0.29238 (16)0.0374 (8)
H330.81140.66000.32650.045*0.50
H33'0.82010.63300.33050.045*0.50
C340.75458 (15)0.6010 (5)0.25019 (16)0.0379 (8)
C350.73591 (17)0.4339 (5)0.2302 (2)0.0539 (12)
H350.76490.34320.24140.065*
C360.67717 (16)0.3952 (5)0.19488 (18)0.0462 (10)
H360.66590.28000.18230.055*
C370.44552 (13)0.6013 (4)0.16512 (13)0.0269 (7)
C380.43350 (13)0.4347 (4)0.14478 (13)0.0267 (7)
H380.46480.36820.14160.032*
C390.37618 (14)0.3624 (4)0.12873 (13)0.0252 (6)
C400.36749 (14)0.1753 (4)0.10990 (14)0.0299 (7)
H40A0.40260.10640.13450.036*
H40B0.36590.16850.07220.036*
C410.30981 (13)0.0976 (4)0.11006 (13)0.0256 (6)
H41A0.30190.01690.09170.031*
H41B0.31420.08180.14840.031*
C420.25784 (13)0.2197 (4)0.07961 (12)0.0215 (6)
H420.25930.25130.04380.026*
C430.19548 (13)0.1471 (4)0.06774 (13)0.0241 (6)
H430.19310.13280.10410.029*
C440.17621 (15)0.0260 (5)0.03742 (15)0.0337 (8)
H44A0.19410.12460.06260.040*
H44B0.18830.03320.00630.040*
C450.10627 (15)0.0241 (5)0.01659 (15)0.0375 (8)
H45A0.08680.05450.02300.045*
H45B0.09320.10850.03750.045*
C460.08903 (14)0.1616 (5)0.02594 (14)0.0323 (7)
H46A0.05300.20180.00620.039*
H46B0.08040.16690.05910.039*
C470.14434 (14)0.2722 (4)0.03357 (13)0.0263 (7)
C480.14362 (15)0.3073 (5)0.02335 (13)0.0330 (8)
H48A0.18060.36880.01910.050*
H48B0.10840.37850.04500.050*
H48C0.14140.19720.04240.050*
C490.15223 (13)0.4399 (4)0.06586 (14)0.0295 (7)
H49A0.14460.41730.09900.035*
H49B0.12200.52520.04280.035*
C500.21556 (13)0.5173 (4)0.08362 (14)0.0267 (7)
H50A0.21980.61720.10820.032*
H50B0.22030.56060.05070.032*
C510.26593 (13)0.3857 (4)0.11363 (12)0.0212 (6)
H510.26150.35180.14800.025*
C520.32922 (12)0.4613 (4)0.13156 (12)0.0214 (6)
C530.34287 (13)0.6289 (4)0.15313 (12)0.0236 (6)
H530.31180.69670.15630.028*
C540.40010 (14)0.6995 (4)0.17005 (12)0.0261 (6)
H540.40820.81330.18480.031*
C550.51180 (17)0.0929 (7)0.07527 (17)0.0532 (11)
H55A0.47050.12480.06920.080*
H55B0.51550.03350.07590.080*
H55C0.52110.13990.04550.080*
C25'0.9021 (3)0.8583 (11)0.3213 (5)0.0329 (9)0.50
H25'0.90040.83640.35760.039*0.50
C26'0.9282 (3)1.0474 (11)0.3304 (4)0.0375 (16)0.50
H26C0.91881.10720.29500.045*0.50
H26D0.91261.11690.35300.045*0.50
C27'0.9963 (3)1.0124 (12)0.3613 (4)0.0450 (17)0.50
H27C1.01121.05700.39950.054*0.50
H27D1.01881.07100.34250.054*0.50
C28'1.0058 (6)0.8123 (13)0.3618 (6)0.0421 (13)0.50
H28C1.03890.78620.35050.051*0.50
H28D1.01730.76730.39960.051*0.50
C29'0.9489 (4)0.7248 (13)0.3231 (4)0.0427 (12)0.50
C30'0.9486 (3)0.6490 (10)0.2694 (3)0.0380 (14)0.50
H30D0.97020.53830.27730.057*0.50
H30E0.96860.73000.25400.057*0.50
H30F0.90690.63070.24280.057*0.50
C31'0.9282 (4)0.5437 (11)0.3375 (3)0.0707 (16)0.50
H31C0.92220.54950.37210.085*0.50
H31D0.95760.45120.34070.085*0.50
C32'0.8661 (3)0.5148 (12)0.2856 (3)0.0390 (17)0.50
H32C0.87080.54140.25120.047*0.50
H32D0.85280.39300.28400.047*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0280 (11)0.0275 (13)0.0546 (15)0.0022 (10)0.0159 (11)0.0072 (11)
O20.0234 (10)0.0343 (14)0.0390 (12)0.0058 (10)0.0132 (9)0.0089 (11)
O30.0248 (11)0.0269 (12)0.0549 (15)0.0049 (10)0.0176 (10)0.0080 (11)
O40.0363 (13)0.0380 (15)0.0503 (14)0.0099 (12)0.0162 (11)0.0130 (13)
C10.0228 (15)0.029 (4)0.046 (3)0.001 (5)0.020 (2)0.003 (4)
C20.026 (2)0.022 (5)0.032 (5)0.005 (3)0.015 (3)0.007 (3)
C30.026 (3)0.022 (4)0.031 (4)0.006 (3)0.019 (3)0.009 (3)
C40.029 (2)0.026 (3)0.035 (4)0.006 (2)0.013 (3)0.006 (2)
C50.047 (3)0.022 (3)0.035 (3)0.007 (3)0.017 (3)0.0009 (19)
C60.035 (3)0.020 (3)0.027 (2)0.006 (3)0.013 (2)0.002 (2)
C70.044 (3)0.033 (3)0.023 (2)0.004 (3)0.011 (2)0.002 (2)
C80.058 (4)0.038 (3)0.039 (3)0.006 (3)0.003 (3)0.004 (3)
C90.075 (5)0.052 (4)0.044 (3)0.011 (4)0.001 (3)0.007 (3)
C100.057 (4)0.053 (4)0.027 (2)0.002 (3)0.006 (2)0.000 (3)
C110.034 (3)0.039 (3)0.0219 (19)0.004 (2)0.0085 (18)0.002 (2)
C120.037 (3)0.048 (5)0.036 (2)0.002 (4)0.013 (2)0.004 (4)
C130.047 (3)0.038 (3)0.033 (2)0.005 (2)0.018 (2)0.005 (2)
C140.041 (3)0.025 (3)0.040 (2)0.005 (2)0.022 (2)0.010 (3)
C150.038 (3)0.023 (3)0.035 (2)0.004 (3)0.023 (2)0.003 (3)
C160.034 (3)0.014 (4)0.036 (2)0.002 (3)0.023 (2)0.008 (3)
C170.038 (3)0.020 (4)0.045 (2)0.003 (3)0.026 (2)0.003 (4)
C180.033 (3)0.025 (6)0.051 (3)0.001 (4)0.030 (2)0.009 (3)
C1'0.0228 (15)0.029 (4)0.046 (3)0.001 (5)0.020 (2)0.003 (4)
C2'0.026 (2)0.022 (5)0.032 (5)0.005 (3)0.015 (3)0.007 (3)
C3'0.026 (3)0.022 (4)0.031 (4)0.006 (3)0.019 (3)0.009 (3)
C4'0.029 (2)0.026 (3)0.035 (4)0.006 (2)0.013 (3)0.006 (2)
C5'0.047 (3)0.022 (3)0.035 (3)0.007 (3)0.017 (3)0.0009 (19)
C6'0.035 (3)0.020 (3)0.027 (2)0.006 (3)0.013 (2)0.002 (2)
C7'0.044 (3)0.033 (3)0.023 (2)0.004 (3)0.011 (2)0.002 (2)
C8'0.058 (4)0.038 (3)0.039 (3)0.006 (3)0.003 (3)0.004 (3)
C9'0.075 (5)0.052 (4)0.044 (3)0.011 (4)0.001 (3)0.007 (3)
C10'0.057 (4)0.053 (4)0.027 (2)0.002 (3)0.006 (2)0.000 (3)
C11'0.034 (3)0.039 (3)0.0219 (19)0.004 (2)0.0085 (18)0.002 (2)
C12'0.037 (3)0.048 (5)0.036 (2)0.002 (4)0.013 (2)0.004 (4)
C13'0.047 (3)0.038 (3)0.033 (2)0.005 (2)0.018 (2)0.005 (2)
C14'0.041 (3)0.025 (3)0.040 (2)0.005 (2)0.022 (2)0.010 (3)
C15'0.038 (3)0.023 (3)0.035 (2)0.004 (3)0.023 (2)0.003 (3)
C16'0.034 (3)0.014 (4)0.036 (2)0.002 (3)0.023 (2)0.008 (3)
C17'0.038 (3)0.020 (4)0.045 (2)0.003 (3)0.026 (2)0.003 (4)
C18'0.033 (3)0.025 (6)0.051 (3)0.001 (4)0.030 (2)0.009 (3)
C190.0209 (14)0.0385 (19)0.0377 (17)0.0043 (14)0.0155 (13)0.0092 (15)
C200.0221 (14)0.0287 (17)0.0320 (15)0.0014 (13)0.0151 (12)0.0029 (13)
C210.0237 (14)0.0288 (17)0.0328 (15)0.0023 (13)0.0175 (13)0.0068 (14)
C220.0232 (15)0.0322 (19)0.0373 (17)0.0026 (13)0.0158 (13)0.0062 (14)
C230.0348 (18)0.0276 (19)0.050 (2)0.0033 (15)0.0043 (16)0.0014 (17)
C240.0187 (14)0.042 (2)0.0257 (15)0.0045 (13)0.0086 (12)0.0033 (14)
C250.0247 (15)0.044 (2)0.026 (2)0.0055 (15)0.0066 (13)0.0100 (16)
C260.028 (2)0.037 (4)0.039 (4)0.007 (2)0.006 (3)0.001 (3)
C270.028 (2)0.055 (4)0.047 (4)0.008 (3)0.011 (3)0.000 (3)
C280.0234 (16)0.054 (4)0.038 (2)0.005 (2)0.0016 (15)0.020 (3)
C290.0170 (17)0.078 (3)0.0282 (18)0.0030 (19)0.0040 (15)0.008 (2)
C300.0261 (19)0.057 (4)0.034 (2)0.014 (3)0.0156 (17)0.006 (3)
C310.0219 (18)0.047 (3)0.119 (4)0.0046 (18)0.004 (2)0.013 (3)
C320.0193 (19)0.041 (3)0.056 (5)0.003 (2)0.015 (3)0.006 (4)
C330.0183 (14)0.0329 (19)0.055 (2)0.0016 (14)0.0092 (14)0.0071 (16)
C340.0238 (16)0.0318 (19)0.059 (2)0.0001 (14)0.0176 (16)0.0104 (18)
C350.0274 (18)0.033 (2)0.091 (3)0.0026 (16)0.015 (2)0.019 (2)
C360.0276 (17)0.032 (2)0.077 (3)0.0046 (15)0.0198 (18)0.022 (2)
C370.0226 (14)0.0235 (16)0.0339 (16)0.0038 (12)0.0108 (12)0.0013 (13)
C380.0227 (14)0.0199 (15)0.0408 (17)0.0028 (12)0.0162 (13)0.0007 (13)
C390.0252 (15)0.0191 (16)0.0318 (15)0.0010 (12)0.0125 (12)0.0005 (13)
C400.0266 (15)0.0190 (16)0.0471 (18)0.0017 (13)0.0181 (14)0.0022 (14)
C410.0249 (14)0.0163 (14)0.0369 (16)0.0017 (12)0.0140 (13)0.0023 (13)
C420.0221 (13)0.0170 (14)0.0273 (14)0.0000 (11)0.0122 (11)0.0005 (12)
C430.0252 (14)0.0209 (16)0.0303 (15)0.0004 (12)0.0155 (12)0.0012 (12)
C440.0335 (17)0.0245 (17)0.0431 (18)0.0040 (14)0.0157 (15)0.0025 (15)
C450.0331 (17)0.035 (2)0.0456 (19)0.0100 (15)0.0169 (15)0.0031 (16)
C460.0234 (14)0.0349 (19)0.0388 (17)0.0049 (14)0.0129 (13)0.0036 (15)
C470.0237 (14)0.0248 (16)0.0323 (16)0.0008 (12)0.0134 (13)0.0028 (13)
C480.0303 (16)0.0347 (19)0.0306 (16)0.0021 (14)0.0090 (14)0.0073 (14)
C490.0223 (14)0.0271 (17)0.0424 (17)0.0044 (13)0.0166 (13)0.0032 (14)
C500.0239 (14)0.0178 (15)0.0406 (17)0.0035 (12)0.0155 (13)0.0025 (13)
C510.0227 (13)0.0151 (14)0.0293 (14)0.0010 (11)0.0141 (11)0.0000 (12)
C520.0196 (13)0.0202 (15)0.0252 (14)0.0006 (11)0.0099 (11)0.0037 (12)
C530.0248 (14)0.0227 (16)0.0250 (14)0.0029 (12)0.0119 (11)0.0011 (12)
C540.0315 (15)0.0188 (15)0.0287 (15)0.0010 (12)0.0131 (12)0.0015 (12)
C550.0352 (19)0.068 (3)0.056 (2)0.008 (2)0.0183 (18)0.021 (2)
C25'0.0247 (15)0.044 (2)0.026 (2)0.0055 (15)0.0066 (13)0.0100 (16)
C26'0.028 (2)0.037 (4)0.039 (4)0.007 (2)0.006 (3)0.001 (3)
C27'0.028 (2)0.055 (4)0.047 (4)0.008 (3)0.011 (3)0.000 (3)
C28'0.0234 (16)0.054 (4)0.038 (2)0.005 (2)0.0016 (15)0.020 (3)
C29'0.0170 (17)0.078 (3)0.0282 (18)0.0030 (19)0.0040 (15)0.008 (2)
C30'0.0261 (19)0.057 (4)0.034 (2)0.014 (3)0.0156 (17)0.006 (3)
C31'0.0219 (18)0.047 (3)0.119 (4)0.0046 (18)0.004 (2)0.013 (3)
C32'0.0193 (19)0.041 (3)0.056 (5)0.003 (2)0.015 (3)0.006 (4)
Geometric parameters (Å, º) top
O1—C1'1.38 (2)C23—H23A0.9900
O1—C11.39 (2)C23—H23B0.9900
O1—H10.8400C24—C331.507 (5)
O1—H1'0.8400C24—C25'1.520 (8)
O2—C191.382 (4)C24—C251.530 (8)
O2—H20.8400C24—H241.0000
O3—C371.378 (4)C24—H24'1.0000
O3—H30.8400C25—C261.549 (9)
O4—C551.402 (4)C25—C291.583 (8)
O4—H40.8400C25—H251.0000
C1—C21.386 (9)C26—C271.571 (7)
C1—C181.388 (10)C26—H26A0.9900
C2—C31.391 (9)C26—H26B0.9900
C2—H2A0.9500C27—C281.595 (9)
C3—C161.394 (7)C27—H27A0.9900
C3—C41.522 (8)C27—H27B0.9900
C4—C51.532 (7)C28—C291.598 (8)
C4—H4A0.9900C28—H28A0.9900
C4—H4B0.9900C28—H28B0.9900
C5—C61.523 (7)C29—C311.352 (11)
C5—H5A0.9900C29—C301.603 (9)
C5—H5B0.9900C30—H30A0.9800
C6—C71.529 (7)C30—H30B0.9800
C6—C151.536 (7)C30—H30C0.9800
C6—H61.0000C31—C321.554 (7)
C7—C81.526 (8)C31—H31A0.9900
C7—C111.536 (8)C31—H31B0.9900
C7—H71.0000C32—C331.503 (6)
C8—C91.542 (8)C32—H32A0.9900
C8—H8A0.9900C32—H32B0.9900
C8—H8B0.9900C33—C341.523 (4)
C9—C101.557 (9)C33—C32'1.588 (7)
C9—H9A0.9900C33—H331.0000
C9—H9B0.9900C33—H33'1.0000
C10—C111.539 (7)C34—C351.399 (5)
C10—H10A0.9900C35—C361.382 (5)
C10—H10B0.9900C35—H350.9500
C11—C121.535 (8)C36—H360.9500
C11—C131.542 (8)C37—C381.380 (5)
C12—H12A0.9800C37—C541.389 (4)
C12—H12B0.9800C38—C391.395 (4)
C12—H12C0.9800C38—H380.9500
C13—C141.550 (7)C39—C521.401 (4)
C13—H13A0.9900C39—C401.515 (4)
C13—H13B0.9900C40—C411.527 (4)
C14—C151.532 (7)C40—H40A0.9900
C14—H14A0.9900C40—H40B0.9900
C14—H14B0.9900C41—C421.517 (4)
C15—C161.536 (8)C41—H41A0.9900
C15—H151.0000C41—H41B0.9900
C16—C171.393 (8)C42—C431.523 (4)
C17—C181.392 (9)C42—C511.535 (4)
C17—H170.9500C42—H421.0000
C18—H18A0.9500C43—C441.532 (4)
C1'—C18'1.390 (10)C43—C471.541 (4)
C1'—C2'1.390 (9)C43—H431.0000
C2'—C3'1.392 (9)C44—C451.557 (5)
C2'—H2'0.9500C44—H44A0.9900
C3'—C16'1.393 (7)C44—H44B0.9900
C3'—C4'1.522 (8)C45—C461.543 (5)
C4'—C5'1.537 (7)C45—H45A0.9900
C4'—H4'A0.9900C45—H45B0.9900
C4'—H4'B0.9900C46—C471.534 (4)
C5'—C6'1.526 (7)C46—H46A0.9900
C5'—H5'A0.9900C46—H46B0.9900
C5'—H5'B0.9900C47—C491.523 (5)
C6'—C15'1.530 (7)C47—C481.534 (4)
C6'—C7'1.536 (7)C48—H48A0.9800
C6'—H6'1.0000C48—H48B0.9800
C7'—C8'1.532 (8)C48—H48C0.9800
C7'—C11'1.535 (8)C49—C501.534 (4)
C7'—H7'1.0000C49—H49A0.9900
C8'—C9'1.541 (8)C49—H49B0.9900
C8'—H8'A0.9900C50—C511.538 (4)
C8'—H8'B0.9900C50—H50A0.9900
C9'—C10'1.539 (9)C50—H50B0.9900
C9'—H9'10.9900C51—C521.527 (4)
C9'—H9'20.9900C51—H511.0000
C10'—C11'1.542 (8)C52—C531.400 (4)
C10'—H10C0.9900C53—C541.385 (4)
C10'—H10D0.9900C53—H530.9500
C11'—C13'1.525 (8)C54—H540.9500
C11'—C12'1.536 (8)C55—H55A0.9800
C12'—H12D0.9800C55—H55B0.9800
C12'—H12E0.9800C55—H55C0.9800
C12'—H12F0.9800C25'—C29'1.521 (7)
C13'—C14'1.546 (8)C25'—C26'1.571 (8)
C13'—H13C0.9900C25'—H25'1.0000
C13'—H13D0.9900C26'—C27'1.540 (8)
C14'—C15'1.535 (7)C26'—H26C0.9900
C14'—H14C0.9900C26'—H26D0.9900
C14'—H14D0.9900C27'—C28'1.562 (9)
C15'—C16'1.548 (8)C27'—H27C0.9900
C15'—H15'1.0000C27'—H27D0.9900
C16'—C17'1.387 (8)C28'—C29'1.503 (9)
C17'—C18'1.393 (9)C28'—H28C0.9900
C17'—H17'0.9500C28'—H28D0.9900
C18'—H18'0.9500C29'—C30'1.546 (8)
C19—C201.382 (5)C29'—C31'1.586 (14)
C19—C361.383 (5)C30'—H30D0.9800
C20—C211.389 (4)C30'—H30E0.9800
C20—H200.9500C30'—H30F0.9800
C21—C341.411 (5)C31'—C32'1.589 (8)
C21—C221.506 (5)C31'—H31C0.9900
C22—C231.510 (4)C31'—H31D0.9900
C22—H22A0.9900C32'—H32C0.9900
C22—H22B0.9900C32'—H32D0.9900
C23—C241.531 (5)
C1—O1—H1120.0C25'—C24—H24104.8
C1'—O1—H1'120.2C25—C24—H24109.7
C1—O1—H1'109.5C23—C24—H24109.7
C19—O2—H2109.5C33—C24—H24'108.0
C37—O3—H3109.5C25'—C24—H24'108.0
C55—O4—H4109.5C25—C24—H24'112.9
C2—C1—C18118.6 (17)C23—C24—H24'108.0
C2—C1—O1116.5 (11)C24—C25—C26113.5 (7)
C18—C1—O1124.5 (12)C24—C25—C29107.7 (6)
C1—C2—C3122.7 (12)C24—C25—H25113.1
C1—C2—H2A118.7C26—C25—H25113.1
C3—C2—H2A118.7C29—C25—H25113.1
C2—C3—C16118.5 (7)C25—C26—C27107.5 (5)
C2—C3—C4116.8 (7)C25—C26—H26A110.2
C16—C3—C4124.6 (7)C27—C26—H26A110.2
C3—C4—C5112.4 (6)C25—C26—H26B110.2
C3—C4—H4A109.1C27—C26—H26B110.2
C5—C4—H4A109.1H26A—C26—H26B108.5
C3—C4—H4B109.1C26—C27—C28103.3 (6)
C5—C4—H4B109.1C26—C27—H27A111.1
H4A—C4—H4B107.8C28—C27—H27A111.1
C6—C5—C4111.9 (5)C26—C27—H27B111.1
C6—C5—H5A109.2C28—C27—H27B111.1
C4—C5—H5A109.2H27A—C27—H27B109.1
C6—C5—H5B109.2C27—C28—C2997.9 (5)
C4—C5—H5B109.2C27—C28—H28A112.2
H5A—C5—H5B107.9C29—C28—H28A112.2
C5—C6—C7111.9 (5)C27—C28—H28B112.2
C5—C6—C15108.2 (5)C29—C28—H28B112.2
C7—C6—C15109.9 (5)H28A—C28—H28B109.8
C5—C6—H6108.9C31—C29—C25111.9 (6)
C7—C6—H6108.9C31—C29—C28114.0 (7)
C15—C6—H6108.9C25—C29—C2898.7 (8)
C8—C7—C6119.6 (6)C31—C29—C30125.5 (7)
C8—C7—C11105.4 (6)C25—C29—C30102.2 (6)
C6—C7—C11112.6 (5)C28—C29—C30100.6 (7)
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C7—C8—C9103.4 (6)C29—C31—H31B107.4
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C8—C9—C10106.2 (7)C33—C32—H32B108.9
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C10—C9—H9A110.5H32A—C32—H32B107.7
C8—C9—H9B110.5C32—C33—C24121.4 (3)
C10—C9—H9B110.5C32—C33—C34116.0 (4)
H9A—C9—H9B108.7C24—C33—C34110.3 (3)
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C11—C10—H10A110.8C34—C33—C32'111.1 (4)
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H10A—C10—H10B108.9C24—C33—H33'110.3
C12—C11—C7113.6 (6)C34—C33—H33'110.3
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C14—C13—H13A109.4C35—C36—C19118.7 (3)
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H13A—C13—H13B108.0O3—C37—C38121.6 (3)
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C15—C14—H14A108.9C38—C37—C54119.9 (3)
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H14A—C14—H14B107.7C38—C39—C52119.9 (3)
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C14—C15—C16113.2 (5)C52—C39—C40122.1 (3)
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H12D—C12'—H12F109.5C39—C52—C51120.9 (3)
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C19—C20—C21121.3 (3)C29'—C28'—H28C109.6
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C20—C21—C22118.7 (3)H28C—C28'—H28D108.1
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C21—C22—C23114.5 (3)C28'—C29'—C30'117.2 (9)
C21—C22—H22A108.6C25'—C29'—C30'120.6 (8)
C23—C22—H22A108.6C28'—C29'—C31'121.7 (8)
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C23—C22—H22B108.6C30'—C29'—C31'90.5 (6)
H22A—C22—H22B107.6C29'—C31'—C32'101.3 (7)
C22—C23—C24113.2 (3)C29'—C31'—H31C111.5
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H23A—C23—H23B107.8C33—C32'—C31'107.0 (6)
C33—C24—C25'111.6 (5)C33—C32'—H32C110.3
C33—C24—C25108.8 (4)C31'—C32'—H32C110.3
C33—C24—C23107.9 (3)C33—C32'—H32D110.3
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C33—C24—H24109.7
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C1'—O1—C1—C18163 (30)C25—C26—C27—C287.4 (11)
C18—C1—C2—C32 (6)C26—C27—C28—C2928.7 (12)
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C1—C2—C3—C162 (4)C26—C25—C29—C31178.8 (7)
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C16—C3—C4—C54.4 (14)C24—C25—C29—C3072.1 (7)
C3—C4—C5—C637.6 (10)C26—C25—C29—C3044.5 (7)
C4—C5—C6—C7174.0 (6)C27—C28—C29—C31173.7 (9)
C4—C5—C6—C1564.8 (7)C27—C28—C29—C2554.9 (11)
C5—C6—C7—C856.1 (9)C27—C28—C29—C3049.4 (11)
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C5—C6—C7—C11179.4 (6)C28—C29—C31—C32157.5 (11)
C15—C6—C7—C1159.2 (7)C30—C29—C31—C3278.1 (11)
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C11—C7—C8—C934.1 (9)C31—C32—C33—C2419.7 (9)
C7—C8—C9—C108.1 (11)C31—C32—C33—C34158.3 (7)
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C6—C7—C11—C1262.9 (8)C25—C24—C33—C3239.4 (7)
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C11—C13—C14—C1552.5 (8)C22—C21—C34—C337.4 (5)
C13—C14—C15—C650.7 (7)C32—C33—C34—C354.0 (7)
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C7—C6—C15—C1452.8 (7)C32—C33—C34—C21177.1 (5)
C5—C6—C15—C1657.3 (7)C24—C33—C34—C2134.1 (5)
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C2—C3—C16—C172.6 (16)C21—C34—C35—C363.6 (7)
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C4—C3—C16—C151.5 (14)O2—C19—C36—C35176.5 (4)
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C3—C16—C17—C183.3 (15)C37—C38—C39—C40176.5 (3)
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C1'—C2'—C3'—C16'1 (4)C51—C42—C43—C4761.8 (3)
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C3'—C4'—C5'—C6'38.3 (9)C44—C45—C46—C4717.7 (4)
C4'—C5'—C6'—C15'65.4 (7)C45—C46—C47—C49155.7 (3)
C4'—C5'—C6'—C7'173.2 (6)C45—C46—C47—C4878.5 (3)
C5'—C6'—C7'—C8'56.8 (9)C45—C46—C47—C4338.9 (3)
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C9'—C10'—C11'—C12'79.7 (9)C49—C50—C51—C4253.1 (3)
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C12'—C11'—C13'—C14'67.3 (8)C40—C39—C52—C53175.6 (3)
C10'—C11'—C13'—C14'166.9 (7)C38—C39—C52—C51179.3 (3)
C11'—C13'—C14'—C15'53.6 (8)C40—C39—C52—C512.2 (4)
C5'—C6'—C15'—C14'176.1 (5)C42—C51—C52—C53167.0 (2)
C7'—C6'—C15'—C14'53.0 (7)C50—C51—C52—C5340.2 (4)
C5'—C6'—C15'—C16'57.3 (7)C42—C51—C52—C3915.3 (4)
C7'—C6'—C15'—C16'179.5 (6)C50—C51—C52—C39142.0 (3)
C13'—C14'—C15'—C6'51.4 (7)C39—C52—C53—C541.7 (4)
C13'—C14'—C15'—C16'176.2 (6)C51—C52—C53—C54179.5 (3)
C2'—C3'—C16'—C17'3.2 (18)C52—C53—C54—C370.5 (5)
C4'—C3'—C16'—C17'177.4 (8)O3—C37—C54—C53179.8 (3)
C2'—C3'—C16'—C15'179.0 (12)C38—C37—C54—C531.5 (5)
C4'—C3'—C16'—C15'0.4 (15)C33—C24—C25'—C29'52.5 (11)
C6'—C15'—C16'—C17'157.2 (7)C25—C24—C25'—C29'107 (6)
C14'—C15'—C16'—C17'30.9 (10)C23—C24—C25'—C29'174.4 (8)
C6'—C15'—C16'—C3'25.0 (11)C33—C24—C25'—C26'164.2 (8)
C14'—C15'—C16'—C3'151.3 (8)C25—C24—C25'—C26'109 (6)
C3'—C16'—C17'—C18'2.7 (15)C23—C24—C25'—C26'42.3 (11)
C15'—C16'—C17'—C18'179.5 (9)C24—C25'—C26'—C27'167.7 (9)
O1—C1'—C18'—C17'179 (3)C29'—C25'—C26'—C27'23.1 (11)
C2'—C1'—C18'—C17'6 (6)C25'—C26'—C27'—C28'6.6 (11)
C16'—C17'—C18'—C1'2 (3)C26'—C27'—C28'—C29'11.4 (16)
O2—C19—C20—C21176.8 (3)C27'—C28'—C29'—C25'24.2 (15)
C36—C19—C20—C212.0 (5)C27'—C28'—C29'—C30'108.4 (13)
C19—C20—C21—C341.2 (5)C27'—C28'—C29'—C31'142.3 (9)
C19—C20—C21—C22176.3 (3)C24—C25'—C29'—C28'176.4 (10)
C20—C21—C22—C23175.0 (3)C26'—C25'—C29'—C28'29.6 (13)
C34—C21—C22—C237.5 (5)C24—C25'—C29'—C30'45.9 (13)
C21—C22—C23—C2434.8 (4)C26'—C25'—C29'—C30'100.9 (10)
C22—C23—C24—C3361.7 (4)C24—C25'—C29'—C31'55.4 (11)
C22—C23—C24—C25'174.4 (6)C26'—C25'—C29'—C31'157.8 (8)
C22—C23—C24—C25179.2 (5)C28'—C29'—C31'—C32'177.9 (10)
C33—C24—C25—C26161.7 (5)C25'—C29'—C31'—C32'63.3 (7)
C25'—C24—C25—C2635 (6)C30'—C29'—C31'—C32'59.2 (6)
C23—C24—C25—C2679.7 (7)C32—C33—C32'—C31'63.4 (10)
C33—C24—C25—C2957.8 (7)C24—C33—C32'—C31'71.2 (6)
C25'—C24—C25—C2969 (6)C34—C33—C32'—C31'169.8 (5)
C23—C24—C25—C29176.5 (6)C29'—C31'—C32'—C3374.4 (6)
C24—C25—C26—C27152.2 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.841.832.662 (3)170
O2—H2···O40.841.822.655 (4)170
O3—H3···O20.841.882.711 (3)173
O4—H4···O1i0.841.902.736 (4)178
Symmetry code: (i) x, y1, z.

Experimental details

Crystal data
Chemical formula3C18H24O·CH4O
Mr801.16
Crystal system, space groupMonoclinic, C2
Temperature (K)100
a, b, c (Å)24.3084 (16), 7.7235 (5), 26.6479 (18)
β (°) 114.292 (1)
V3)4560.1 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.35 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.976, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
21707, 5612, 4481
Rint0.050
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.141, 1.02
No. of reflections5612
No. of parameters616
No. of restraints234
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.33
Absolute structure2199 Friedel pairs were merged

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and QMOL (Gans & Shalloway, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.841.832.662 (3)170
O2—H2···O40.841.822.655 (4)170
O3—H3···O20.841.882.711 (3)173
O4—H4···O1i0.841.902.736 (4)178
Symmetry code: (i) x, y1, z.
 

Footnotes

Additional correspondence author, e-mail: kketuly@gmail.com.

Acknowledgements

The authors thank the University of Malaya for support and greatly appreciate UMRG grant No. RG035/10BIO.

References

First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationGans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557–559.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHuang-Minlon (1949). J. Am. Chem. Soc. 71, 3301–3303.  Google Scholar
First citationKetuly, K. A. & Hadi, A. H. (2010). Molecules, 15, 2347–2356.  Web of Science CrossRef CAS PubMed Google Scholar
First citationKetuly, K. A., Hadi, A. H. A., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2265.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKetuly, K. A., Yufit, D. S., Brooks, C. J. W. & Freer, A. A. (1997). Acta Cryst. C53, 981–982.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationRajnikant, Dinesh, & Bhavnaish, C. (2006). Acta Cryst. A62, 136–145.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Pages o1160-o1161
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