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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 4| April 2011| Pages o773-o774
doi:10.1107/S1600536811007306

3β-Acet­­oxy-6-hy­dr­oxy­imino­cholestane

Kamal Aziz Ketuly,a‡ A. Hamid A. Hadi,a Seik Weng Nga and Edward R. T. Tiekinka*

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

(Received 25 February 2011; accepted 25 February 2011; online 5 March 2011)

Two independent mol­ecules comprise the asymmetric unit of the title cholestane derivative, C29H49NO3 {systematic name: (3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethyl­hex­yl]-6-hy­droxy­imino-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetra­deca­hydro-1H-cyclo­penta­[a]phenanthren-3-yl ace­tate}. The major differences between the mol­ecules relate to the relative orientations of the terminal acetyl [C—C—O—C torsion angles = −158.8 (3) and −81.7 (3)°] and alkyl groups [C—C—C—C = 168.9 (3) and 65.8 (4)°]. In the crystal, the independent mol­ecules associate via pairs of O—H⋯N hydrogen bonds, forming dimeric aggregates. Supra­molecular layers in the ab plane are mediated by C—H⋯O inter­actions.

Related literature

For background to this study and further details of the synthetic procedures, see: Ketuly & Hadi (2010[Ketuly, K. A. & A. Hadi, A. H. (2010). Molecules, 15, 2347-2356.]). For previous syntheses, see: Anagnostopoulos & Fieser (1954[Anagnostopoulos, C. E. & Fieser, L. F. (1954). J. Am. Chem. Soc. 76, 532-536.]); Petersen (1963[Petersen, Q. R. (1963). Proc. Indiana Acad. Sci. 73, 127-131.]); Choucair et al. (2004[Choucair, B., Dherbomez, M., Roussakis, C. & Kihel, L. El. (2004). Tetrahedron Lett. 60, 11477-11486.]). 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.]). For ring conformational analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C29H49NO3

  • Mr = 459.69

  • Monoclinic, P 21

  • a = 11.3934 (13) Å

  • b = 9.6588 (11) Å

  • c = 25.018 (3) Å

  • β = 93.466 (2)°

  • V = 2748.1 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.35 × 0.30 × 0.03 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 = 0.757, Tmax = 0.862

  • 26531 measured reflections

  • 6690 independent reflections

  • 4553 reflections with I > 2σ(I)

  • Rint = 0.086
Refinement

  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.114

  • S = 0.99

  • 6690 reflections

  • 615 parameters

  • 1 restraint

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

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.23 e Å−3

  • Absolute structure: nd

  • Flack parameter: ?

  • Rogers parameter: ?

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N2 0.98 (4) 1.88 (4) 2.809 (3) 157 (4)
O4—H4⋯N1 0.95 (4) 1.82 (4) 2.733 (3) 160 (3)
C9—H9c⋯O6i 0.98 2.58 3.404 (4) 142
C37—H37c⋯O3ii 0.98 2.40 3.373 (4) 169
Symmetry codes: (i) x+1, y, z; (ii) [-x+2, y-{\script{1\over 2}}, -z+1].

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. Molec. Graphics 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

Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536811007306/hb5806sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007306/hb5806Isup2.hkl

checkCIF report


Comment top

The title compound, 3β-Acetoxy-6 N-hydroxyiminocholestane, (I), is a known species and has been utilized as an intermediate for the preparation of 6-ketocholestanol acetate, which it readily affords upon reduction with zinc and acetic acid followed by acid hydrolysis (Anagnostopoulos & Fieser, 1954; Petersen, 1963). Interest in hydroxyimino-steroids stems from a broad investigation into the correlation of structure with biological activity of modified steroid hormones (Choucair et al., 2004). In continuation of systematic structural analyses of related steroidal compounds (Ketuly et al., 1997; Ketuly et al., 2010), the X-ray crystallographic analysis of (I) was conducted.

Two independent molecules comprise the asymmetric unit of (I), Fig. 1. These are linked into dimeric aggregates via O—H···N hydrogen bonds, Table 1. From the overlay diagram, Fig. 3, it is evident that the molecules differ in the relative orientations of the terminal acetyl and alkyl substituents. For the former, the different conformation is manifested in the values of the C3—C4—O2—C8 and C30—C31—O5—C36 torsion angles of -158.8 (3) and -81.7 (3) °, respectively. For the alkyl chains, the differences are seen in the C22—C24—C25—C26 and C51—C53—C54—C55 torsion angles of 168.9 (3) and 65.8 (4) °, respectively. Each of the six-membered rings adopts a chair conformation or close to a chair conformation, and each of the five-membered rings has a twisted conformation, about the C14—C15 and C42—C43 bonds, respectively (Cremer & Pople, 1975).

The most notable feature of the crystal packing other than the aforementioned O—H···N hydrogen bonds is the presence of C—H···O interactions, Table 1. These lead to the formation of supramolecular layers in the ab plane, Fig. 3.

Related literature top

For background to this study and further details of the synthetic procedures, see: Ketuly & Hadi (2010). For previous syntheses, see: Anagnostopoulos & Fieser (1954); Petersen (1963); Choucair et al. (2004). For related structures, see: Ketuly et al. (1997, 2010). For ring conformational analysis, see: Cremer & Pople (1975).

Experimental top

Hydroxylamine hydrochloride (13.5 mg) was dissolved in dried and purified pyridine (2 ml) and 3β-acetoxy-5α-chloestan-6-one (10 mg) added. The solution mixture was heated at 353 K for 4 h. The solvent was dried under vacuum, yielding crude crystals. Recrystallization from methanol and water (10:1, v/v) yielded compound (I): yield 9.1 mg, 88%, M.pt. 474–475 K. Lit. M.pt. 475–476 K (Petersen, 1963). Compound (I) was also isolated as an intermediate byproduct during the reduction of 3β-acetoxy-6-nitrocholest-5-ene to 3β-acetoxy-6-oxo-cholestanol. Thus, 3β-acetoxy-6-nitrocholest-5-ene (5 g, 10.6 mmol) was dissolved in glacial acetic acid (100 ml) and stirred with a Hershbury stirrer and diluted with water (5 ml). Zinc dust (10 g) was added in small portions over a period of 0.5 h. The suspension was then heated under reflux for 4.5 h. The solution was filtered and washed with acetic acid (2 x 6.5 ml). The filtrate was diluted with water (100 ml), cooled in an ice-bath and the organic layer was extracted with ether. The yellow viscous product was crystallized from methanol, dried (4.41 g) and recrystallized four times from methanol with a few drops of ether, yielding 3β-acetoxy-6-oxo-cholestanol (3.12 g), M.pt. 402–404 K. Lit. 409 K (Choucair et al., 2004). The combined mother liquors were dried and four times recrystallized from methanol and water (10:1, v/v), yielding colourless plates of (I), (0.24 g), M.pt. 474–475 K. The purification and vacuum sublimation methods employed in the study follow literature precedents (Ketuly & Hadi, 2010).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.98 to 1.00 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Uequiv(C). The oxygen-bound H atoms were located from a difference map and refined freely. In the absence of significant anomalous scattering effects, 5428 Friedel pairs were averaged in the final refinement. However, the absolute configuration was assigned on the basis of the known chirality of the 3β-acetoxy-5α-chloestan-6-one starting material. Two reflections, i.e. (0 0 1) and (0 0 2), were omitted from the final refinement owing to poor agreement.

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 two independent molecules comprising the asymmetric unit of (I) showing displacement ellipsoids at the 50% probability level. The molecules are connected into dimeric aggregates via pairs of O—H···N hydrogen bonds (dashed lines).
[Figure 2] Fig. 2. Overlay diagram the two independent molecules comprising the asymmetric unit of (I). The independent molecule having the N1 atom is shown in red.
[Figure 3] Fig. 3. View in projection down the a axis of the crystal packing of (I). The O—H···N hydrogen bonds and C—H···O contacts are shown as orange and blue dashed lines, respectively.
(3S,8S,9S,10R,13R,14S,17R)- 17-[(1R)-1,5-dimethylhexyl]-6-hydroxyimino-10,13-dimethyl- 2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H- cyclopenta[a]phenanthren-3-yl acetate top
Crystal data top
C29H49NO3F(000) = 1016
Mr = 459.69Dx = 1.111 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2461 reflections
a = 11.3934 (13) Åθ = 2.3–20.8°
b = 9.6588 (11) ŵ = 0.07 mm−1
c = 25.018 (3) ÅT = 100 K
β = 93.466 (2)°Plate, colourless
V = 2748.1 (5) Å30.35 × 0.30 × 0.03 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer		6690 independent reflections
Radiation source: fine-focus sealed tube4553 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.086
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.757, Tmax = 0.862k = −11→12
26531 measured reflectionsl = −32→32
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)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0489P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
6690 reflectionsΔρmax = 0.24 e Å−3
615 parametersΔρmin = −0.23 e Å−3
1 restraintAbsolute structure: nd
Primary atom site location: structure-invariant direct methods
Crystal data top
C29H49NO3V = 2748.1 (5) Å3
Mr = 459.69Z = 4
Monoclinic, P21Mo Kα radiation
a = 11.3934 (13) ŵ = 0.07 mm−1
b = 9.6588 (11) ÅT = 100 K
c = 25.018 (3) Å0.35 × 0.30 × 0.03 mm
β = 93.466 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer		6690 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4553 reflections with I > 2σ(I)
Tmin = 0.757, Tmax = 0.862Rint = 0.086
26531 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0501 restraint
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.24 e Å−3
6690 reflectionsΔρmin = −0.23 e Å−3
615 parametersAbsolute structure: nd
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.84194 (18)0.5005 (3)0.55612 (8)0.0249 (5)
O21.37405 (18)0.6484 (2)0.51114 (8)0.0238 (5)
O31.4744 (2)0.8086 (3)0.46763 (10)0.0369 (7)
O41.08653 (19)0.4934 (3)0.62945 (9)0.0321 (6)
O50.55480 (19)0.3995 (2)0.69942 (9)0.0261 (5)
O60.5309 (2)0.6211 (3)0.67381 (10)0.0321 (6)
N10.9531 (2)0.5325 (3)0.53618 (10)0.0191 (6)
N20.9777 (2)0.4768 (3)0.65324 (10)0.0240 (6)
C10.9457 (3)0.5799 (3)0.48875 (12)0.0182 (7)
C21.0580 (3)0.6150 (3)0.46315 (12)0.0186 (7)
H21.04850.71200.44950.022*
C31.1680 (3)0.6152 (4)0.50172 (12)0.0208 (7)
H3A1.15540.67700.53240.025*
H3B1.18290.52060.51570.025*
C41.2728 (3)0.6646 (4)0.47275 (12)0.0221 (7)
H4A1.26270.76430.46270.027*
C51.2916 (3)0.5790 (4)0.42338 (12)0.0230 (8)
H5A1.31420.48370.43430.028*
H5B1.35690.61920.40410.028*
C61.1800 (3)0.5736 (4)0.38548 (12)0.0230 (7)
H6A1.19470.51220.35490.028*
H6B1.16370.66760.37110.028*
C71.0709 (3)0.5212 (3)0.41278 (11)0.0177 (7)
C81.4698 (3)0.7243 (4)0.50283 (14)0.0261 (8)
C91.5689 (3)0.6876 (4)0.54238 (14)0.0322 (9)
H9A1.64070.73510.53280.048*
H9B1.58170.58720.54190.048*
H9C1.54920.71630.57830.048*
C101.0868 (3)0.3688 (3)0.42964 (13)0.0235 (7)
H10A1.15210.36130.45680.035*
H10B1.10400.31300.39840.035*
H10C1.01440.33510.44450.035*
C110.9585 (3)0.5404 (3)0.37497 (11)0.0181 (7)
H110.95680.63990.36400.022*
C120.9603 (3)0.4552 (3)0.32305 (12)0.0209 (7)
H12A0.96720.35580.33240.025*
H12B1.03070.48120.30400.025*
C130.8498 (3)0.4763 (4)0.28501 (12)0.0226 (7)
H13A0.84840.57260.27150.027*
H13B0.85370.41350.25390.027*
C140.7370 (3)0.4477 (3)0.31316 (12)0.0190 (7)
C150.7391 (3)0.5408 (3)0.36309 (11)0.0192 (7)
H150.74780.63810.35020.023*
C160.8436 (3)0.5132 (3)0.40277 (11)0.0174 (7)
H160.84190.41340.41320.021*
C170.8359 (3)0.6006 (4)0.45354 (12)0.0210 (7)
H17A0.82730.69960.44390.025*
H17B0.76650.57240.47280.025*
C180.7281 (3)0.2929 (3)0.32761 (13)0.0239 (8)
H18A0.65530.27650.34550.036*
H18B0.79560.26670.35160.036*
H18C0.72780.23720.29490.036*
C190.6195 (3)0.4962 (3)0.28363 (11)0.0195 (7)
H190.63350.58970.26800.023*
C200.5362 (3)0.5155 (4)0.33006 (12)0.0251 (8)
H20A0.48770.59990.32410.030*
H20B0.48300.43490.33210.030*
C210.6149 (3)0.5290 (4)0.38261 (12)0.0241 (8)
H21A0.59400.61250.40290.029*
H21B0.60750.44640.40560.029*
C220.5642 (3)0.4040 (3)0.23836 (12)0.0220 (7)
H220.54990.31060.25390.026*
C230.6450 (3)0.3848 (4)0.19192 (12)0.0268 (8)
H23A0.60100.34050.16170.040*
H23B0.71200.32640.20370.040*
H23C0.67370.47540.18070.040*
C240.4450 (3)0.4623 (3)0.21712 (13)0.0255 (8)
H24A0.40270.49760.24770.031*
H24B0.45900.54160.19330.031*
C250.3664 (3)0.3576 (4)0.18636 (13)0.0280 (8)
H25A0.36450.27070.20730.034*
H25B0.40090.33630.15190.034*
C260.2406 (3)0.4099 (4)0.17519 (14)0.0293 (8)
H26A0.21340.45120.20850.035*
H26B0.24150.48430.14800.035*
C270.1525 (3)0.3005 (4)0.15556 (13)0.0263 (8)
H270.15810.22200.18160.032*
C280.0275 (3)0.3572 (4)0.15502 (15)0.0394 (10)
H28A0.01060.38740.19120.059*
H28B−0.02830.28460.14310.059*
H28C0.01970.43610.13040.059*
C290.1768 (3)0.2427 (5)0.10086 (15)0.0417 (10)
H29A0.25460.19920.10250.063*
H29B0.17450.31800.07460.063*
H29C0.11690.17360.09020.063*
C300.7648 (3)0.4453 (4)0.69849 (12)0.0215 (7)
H30A0.75330.51990.67160.026*
H30B0.77320.35670.67920.026*
C310.6589 (3)0.4380 (3)0.73216 (12)0.0228 (7)
H310.64620.53050.74880.027*
C320.6743 (3)0.3301 (3)0.77571 (12)0.0242 (8)
H32A0.67890.23710.75930.029*
H32B0.60530.33160.79790.029*
C330.7860 (3)0.3571 (4)0.81116 (12)0.0242 (8)
H33A0.79550.28230.83810.029*
H33B0.77700.44540.83060.029*
C340.8974 (3)0.3646 (3)0.77964 (12)0.0196 (7)
C350.8765 (3)0.4736 (3)0.73399 (12)0.0193 (7)
H350.86400.56440.75200.023*
C360.4993 (3)0.5018 (4)0.67105 (13)0.0271 (8)
C370.3957 (3)0.4475 (4)0.63748 (14)0.0316 (9)
H37A0.34140.52370.62820.047*
H37B0.35510.37700.65770.047*
H37C0.42290.40630.60460.047*
C380.9238 (3)0.2221 (3)0.75585 (13)0.0224 (7)
H38A0.95340.15980.78450.034*
H38B0.98320.23200.72940.034*
H38C0.85160.18350.73850.034*
C391.0043 (3)0.4165 (3)0.81616 (11)0.0197 (7)
H390.98500.51350.82650.024*
C401.0249 (3)0.3368 (4)0.86832 (12)0.0277 (8)
H40A1.03830.23810.85990.033*
H40B0.95290.34220.88850.033*
C411.1297 (3)0.3902 (4)0.90420 (12)0.0265 (8)
H41A1.11270.48520.91640.032*
H41B1.14060.33030.93620.032*
C421.2428 (3)0.3912 (3)0.87421 (12)0.0220 (7)
C431.2180 (3)0.4791 (3)0.82297 (11)0.0201 (7)
H431.19390.57280.83530.024*
C441.1168 (3)0.4260 (3)0.78592 (12)0.0206 (7)
H441.13720.33130.77320.025*
C451.0981 (3)0.5218 (4)0.73689 (11)0.0229 (7)
H45A1.09530.61900.74920.028*
H45B1.16580.51240.71420.028*
C460.9867 (3)0.4894 (3)0.70391 (11)0.0201 (7)
C471.2818 (3)0.2435 (3)0.86097 (13)0.0286 (8)
H47A1.22100.19910.83740.043*
H47B1.29340.18990.89420.043*
H47C1.35570.24710.84290.043*
C481.3496 (3)0.4747 (3)0.90062 (12)0.0239 (7)
H481.31760.56330.91450.029*
C491.4219 (3)0.5117 (4)0.85183 (12)0.0265 (8)
H49A1.45180.60770.85520.032*
H49B1.48980.44830.85010.032*
C501.3397 (3)0.4970 (4)0.80088 (12)0.0254 (8)
H50A1.34250.58080.77820.030*
H50B1.36110.41530.77970.030*
C511.4265 (3)0.4091 (4)0.94657 (12)0.0270 (8)
H511.46690.32630.93230.032*
C521.3565 (3)0.3630 (4)0.99354 (13)0.0351 (9)
H52A1.30370.28710.98210.053*
H52B1.31010.44101.00580.053*
H52C1.41070.33131.02290.053*
C531.5206 (3)0.5147 (4)0.96584 (14)0.0333 (9)
H53A1.55810.55140.93410.040*
H53B1.48080.59320.98260.040*
C541.6177 (3)0.4619 (4)1.00560 (15)0.0402 (10)
H54A1.58110.42131.03690.048*
H54B1.66670.54111.01850.048*
C551.6970 (3)0.3526 (4)0.98144 (14)0.0347 (9)
H55A1.65280.26460.97750.042*
H55B1.71610.38330.94520.042*
C561.8112 (3)0.3258 (4)1.01455 (15)0.0410 (10)
H561.79150.30761.05230.049*
C571.8932 (3)0.4494 (5)1.01459 (17)0.0476 (11)
H57A1.96740.42621.03450.071*
H57B1.85650.52831.03170.071*
H57C1.90870.47350.97760.071*
C581.8720 (3)0.1987 (5)0.99400 (17)0.0490 (12)
H58A1.94530.18251.01570.073*
H58B1.88980.21320.95660.073*
H58C1.82030.11810.99650.073*
H10.871 (4)0.480 (5)0.5931 (17)0.075 (15)*
H41.057 (3)0.508 (4)0.5936 (15)0.047 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0188 (12)0.0347 (14)0.0221 (11)−0.0064 (11)0.0073 (10)0.0009 (11)
O20.0167 (12)0.0278 (14)0.0271 (12)−0.0059 (10)0.0026 (10)0.0033 (10)
O30.0334 (16)0.0372 (16)0.0408 (15)−0.0089 (12)0.0073 (12)0.0070 (13)
O40.0194 (13)0.0555 (18)0.0222 (12)−0.0054 (13)0.0060 (10)0.0065 (12)
O50.0205 (12)0.0240 (13)0.0341 (12)0.0005 (10)0.0049 (10)−0.0047 (11)
O60.0284 (14)0.0222 (14)0.0455 (15)0.0027 (11)0.0015 (12)−0.0042 (12)
N10.0170 (14)0.0208 (15)0.0202 (13)−0.0027 (12)0.0059 (11)−0.0026 (11)
N20.0165 (14)0.0330 (18)0.0235 (13)−0.0007 (13)0.0086 (11)0.0025 (13)
C10.0174 (17)0.0172 (17)0.0201 (15)−0.0003 (13)0.0026 (13)−0.0069 (13)
C20.0180 (17)0.0161 (17)0.0220 (16)−0.0003 (14)0.0053 (14)0.0015 (13)
C30.0165 (17)0.0248 (18)0.0213 (16)−0.0005 (14)0.0027 (13)0.0021 (14)
C40.0201 (18)0.0217 (18)0.0241 (16)−0.0019 (14)−0.0018 (14)0.0029 (14)
C50.0183 (18)0.0266 (19)0.0246 (16)−0.0005 (15)0.0056 (14)0.0027 (15)
C60.0216 (18)0.0265 (19)0.0213 (16)0.0017 (15)0.0046 (14)0.0018 (14)
C70.0191 (17)0.0177 (17)0.0164 (14)0.0001 (14)0.0036 (12)0.0019 (13)
C80.019 (2)0.027 (2)0.0336 (19)−0.0044 (15)0.0083 (16)−0.0056 (16)
C90.023 (2)0.037 (2)0.037 (2)−0.0075 (17)0.0029 (16)−0.0066 (17)
C100.0207 (18)0.0208 (18)0.0289 (17)0.0035 (15)0.0023 (14)−0.0007 (14)
C110.0152 (17)0.0191 (18)0.0204 (15)0.0002 (13)0.0034 (13)0.0018 (13)
C120.0189 (17)0.0221 (18)0.0219 (15)−0.0020 (14)0.0039 (13)−0.0032 (14)
C130.0237 (18)0.0242 (19)0.0205 (15)−0.0010 (15)0.0055 (13)−0.0018 (14)
C140.0176 (17)0.0175 (17)0.0220 (15)−0.0019 (14)0.0014 (13)−0.0008 (13)
C150.0187 (17)0.0177 (17)0.0215 (15)0.0024 (13)0.0037 (13)0.0000 (13)
C160.0180 (16)0.0172 (16)0.0174 (14)0.0004 (14)0.0046 (12)−0.0005 (13)
C170.0185 (18)0.0238 (19)0.0212 (16)0.0029 (14)0.0051 (14)−0.0011 (14)
C180.0229 (19)0.0215 (19)0.0273 (17)0.0015 (15)0.0020 (14)−0.0015 (14)
C190.0200 (17)0.0168 (17)0.0218 (15)−0.0002 (14)0.0015 (13)0.0032 (13)
C200.0206 (18)0.0278 (19)0.0266 (16)0.0016 (15)0.0001 (14)−0.0058 (15)
C210.0216 (18)0.029 (2)0.0216 (15)0.0011 (15)0.0032 (14)−0.0016 (15)
C220.0242 (18)0.0155 (17)0.0258 (16)−0.0011 (14)−0.0015 (14)−0.0001 (14)
C230.0273 (19)0.026 (2)0.0270 (17)−0.0027 (16)0.0011 (15)−0.0014 (15)
C240.0243 (18)0.0207 (18)0.0311 (17)−0.0006 (15)−0.0014 (14)−0.0005 (15)
C250.026 (2)0.025 (2)0.0325 (18)0.0037 (16)−0.0030 (15)−0.0027 (16)
C260.026 (2)0.028 (2)0.0332 (19)0.0033 (15)−0.0019 (15)−0.0047 (16)
C270.029 (2)0.024 (2)0.0250 (17)−0.0034 (16)0.0001 (15)−0.0007 (15)
C280.027 (2)0.053 (3)0.039 (2)−0.0072 (19)0.0044 (17)−0.016 (2)
C290.031 (2)0.055 (3)0.038 (2)0.002 (2)−0.0019 (18)−0.017 (2)
C300.0213 (18)0.0215 (18)0.0221 (16)0.0015 (14)0.0043 (14)−0.0013 (14)
C310.0185 (17)0.0217 (18)0.0287 (17)−0.0021 (14)0.0045 (14)−0.0049 (14)
C320.0238 (19)0.0221 (19)0.0282 (17)−0.0023 (15)0.0123 (15)−0.0010 (15)
C330.0251 (19)0.0262 (19)0.0221 (16)−0.0004 (15)0.0074 (14)−0.0025 (14)
C340.0234 (18)0.0173 (17)0.0186 (15)−0.0005 (14)0.0063 (13)−0.0014 (13)
C350.0208 (17)0.0148 (17)0.0229 (15)0.0002 (14)0.0045 (13)−0.0025 (13)
C360.0207 (18)0.030 (2)0.0315 (18)0.0058 (17)0.0092 (15)−0.0065 (17)
C370.0237 (19)0.032 (2)0.040 (2)−0.0006 (16)0.0034 (16)−0.0063 (17)
C380.0252 (19)0.0195 (18)0.0228 (16)−0.0020 (14)0.0039 (14)−0.0037 (14)
C390.0249 (18)0.0183 (17)0.0169 (14)−0.0016 (14)0.0086 (13)0.0004 (13)
C400.027 (2)0.034 (2)0.0231 (17)−0.0049 (16)0.0051 (15)0.0022 (15)
C410.029 (2)0.030 (2)0.0216 (16)−0.0045 (16)0.0048 (15)0.0032 (15)
C420.0266 (19)0.0165 (17)0.0236 (16)0.0016 (14)0.0066 (14)0.0017 (14)
C430.0229 (17)0.0190 (18)0.0190 (15)0.0013 (14)0.0059 (13)0.0004 (13)
C440.0236 (18)0.0178 (17)0.0209 (15)0.0010 (14)0.0057 (14)−0.0023 (13)
C450.0244 (18)0.0271 (19)0.0175 (15)−0.0037 (16)0.0033 (13)0.0032 (14)
C460.0245 (18)0.0158 (17)0.0205 (15)−0.0009 (14)0.0056 (13)0.0023 (13)
C470.041 (2)0.0193 (19)0.0251 (17)0.0022 (16)0.0003 (16)0.0011 (15)
C480.0304 (19)0.0177 (18)0.0238 (16)0.0013 (15)0.0026 (14)−0.0007 (14)
C490.0236 (18)0.0265 (19)0.0294 (17)0.0019 (16)0.0020 (14)−0.0013 (16)
C500.0257 (19)0.0244 (19)0.0263 (16)0.0003 (16)0.0042 (14)0.0011 (15)
C510.032 (2)0.0235 (19)0.0245 (17)0.0075 (16)−0.0040 (15)−0.0033 (15)
C520.040 (2)0.035 (2)0.0294 (18)0.0081 (18)−0.0026 (17)0.0001 (17)
C530.035 (2)0.026 (2)0.0374 (19)0.0044 (17)−0.0083 (16)−0.0069 (17)
C540.035 (2)0.045 (3)0.040 (2)0.0048 (19)−0.0099 (17)−0.0055 (19)
C550.040 (2)0.031 (2)0.0341 (19)0.0023 (18)0.0026 (17)0.0048 (17)
C560.032 (2)0.053 (3)0.037 (2)0.000 (2)0.0018 (17)0.020 (2)
C570.035 (2)0.050 (3)0.057 (3)−0.006 (2)−0.004 (2)0.010 (2)
C580.038 (3)0.049 (3)0.061 (3)0.006 (2)0.011 (2)0.025 (2)
Geometric parameters (Å, º) top
O1—N11.422 (3)C28—H28A0.9800
O1—H10.98 (4)C28—H28B0.9800
O2—C81.341 (4)C28—H28C0.9800
O2—C41.464 (3)C29—H29A0.9800
O3—C81.202 (4)C29—H29B0.9800
O4—N21.417 (3)C29—H29C0.9800
O4—H40.95 (4)C30—C311.514 (4)
O5—C361.352 (4)C30—C351.533 (4)
O5—C311.449 (4)C30—H30A0.9900
O6—C361.208 (4)C30—H30B0.9900
N1—C11.270 (4)C31—C321.510 (4)
N2—C461.272 (4)C31—H311.0000
C1—C171.499 (4)C32—C331.529 (4)
C1—C21.504 (4)C32—H32A0.9900
C2—C31.535 (4)C32—H32B0.9900
C2—C71.566 (4)C33—C341.536 (4)
C2—H21.0000C33—H33A0.9900
C3—C41.511 (4)C33—H33B0.9900
C3—H3A0.9900C34—C381.536 (4)
C3—H3B0.9900C34—C391.560 (4)
C4—C51.513 (4)C34—C351.561 (4)
C4—H4A1.0000C35—C461.510 (4)
C5—C61.540 (4)C35—H351.0000
C5—H5A0.9900C36—C371.501 (4)
C5—H5B0.9900C37—H37A0.9800
C6—C71.540 (4)C37—H37B0.9800
C6—H6A0.9900C37—H37C0.9800
C6—H6B0.9900C38—H38A0.9800
C7—C101.539 (4)C38—H38B0.9800
C7—C111.556 (4)C38—H38C0.9800
C8—C91.498 (5)C39—C401.521 (4)
C9—H9A0.9800C39—C441.530 (4)
C9—H9B0.9800C39—H391.0000
C9—H9C0.9800C40—C411.539 (4)
C10—H10A0.9800C40—H40A0.9900
C10—H10B0.9800C40—H40B0.9900
C10—H10C0.9800C41—C421.530 (4)
C11—C121.538 (4)C41—H41A0.9900
C11—C161.542 (4)C41—H41B0.9900
C11—H111.0000C42—C471.537 (5)
C12—C131.545 (4)C42—C431.549 (4)
C12—H12A0.9900C42—C481.571 (4)
C12—H12B0.9900C43—C441.524 (4)
C13—C141.527 (4)C43—C501.533 (4)
C13—H13A0.9900C43—H431.0000
C13—H13B0.9900C44—C451.541 (4)
C14—C151.538 (4)C44—H441.0000
C14—C181.543 (4)C45—C461.504 (4)
C14—C191.562 (4)C45—H45A0.9900
C15—C161.527 (4)C45—H45B0.9900
C15—C211.529 (4)C47—H47A0.9800
C15—H151.0000C47—H47B0.9800
C16—C171.532 (4)C47—H47C0.9800
C16—H161.0000C48—C511.539 (4)
C17—H17A0.9900C48—C491.555 (4)
C17—H17B0.9900C48—H481.0000
C18—H18A0.9800C49—C501.542 (4)
C18—H18B0.9800C49—H49A0.9900
C18—H18C0.9800C49—H49B0.9900
C19—C221.545 (4)C50—H50A0.9900
C19—C201.555 (4)C50—H50B0.9900
C19—H191.0000C51—C521.526 (5)
C20—C211.552 (4)C51—C531.537 (5)
C20—H20A0.9900C51—H511.0000
C20—H20B0.9900C52—H52A0.9800
C21—H21A0.9900C52—H52B0.9800
C21—H21B0.9900C52—H52C0.9800
C22—C241.535 (4)C53—C541.530 (4)
C22—C231.537 (4)C53—H53A0.9900
C22—H221.0000C53—H53B0.9900
C23—H23A0.9800C54—C551.537 (5)
C23—H23B0.9800C54—H54A0.9900
C23—H23C0.9800C54—H54B0.9900
C24—C251.527 (4)C55—C561.521 (5)
C24—H24A0.9900C55—H55A0.9900
C24—H24B0.9900C55—H55B0.9900
C25—C261.529 (4)C56—C581.515 (6)
C25—H25A0.9900C56—C571.516 (5)
C25—H25B0.9900C56—H561.0000
C26—C271.519 (4)C57—H57A0.9800
C26—H26A0.9900C57—H57B0.9800
C26—H26B0.9900C57—H57C0.9800
C27—C291.519 (5)C58—H58A0.9800
C27—C281.525 (5)C58—H58B0.9800
C27—H271.0000C58—H58C0.9800
N1—O1—H197 (2)C27—C29—H29C109.5
C8—O2—C4117.1 (3)H29A—C29—H29C109.5
N2—O4—H499 (2)H29B—C29—H29C109.5
C36—O5—C31116.8 (3)C31—C30—C35110.3 (2)
C1—N1—O1113.3 (2)C31—C30—H30A109.6
C46—N2—O4112.8 (2)C35—C30—H30A109.6
N1—C1—C17127.1 (3)C31—C30—H30B109.6
N1—C1—C2118.0 (3)C35—C30—H30B109.6
C17—C1—C2114.9 (3)H30A—C30—H30B108.1
C1—C2—C3114.6 (2)O5—C31—C32106.6 (3)
C1—C2—C7109.6 (2)O5—C31—C30110.5 (2)
C3—C2—C7113.2 (3)C32—C31—C30111.8 (3)
C1—C2—H2106.3O5—C31—H31109.3
C3—C2—H2106.3C32—C31—H31109.3
C7—C2—H2106.3C30—C31—H31109.3
C4—C3—C2109.7 (2)C31—C32—C33110.9 (3)
C4—C3—H3A109.7C31—C32—H32A109.5
C2—C3—H3A109.7C33—C32—H32A109.5
C4—C3—H3B109.7C31—C32—H32B109.5
C2—C3—H3B109.7C33—C32—H32B109.5
H3A—C3—H3B108.2H32A—C32—H32B108.0
O2—C4—C3105.4 (2)C32—C33—C34113.3 (3)
O2—C4—C5109.4 (3)C32—C33—H33A108.9
C3—C4—C5112.0 (3)C34—C33—H33A108.9
O2—C4—H4A110.0C32—C33—H33B108.9
C3—C4—H4A110.0C34—C33—H33B108.9
C5—C4—H4A110.0H33A—C33—H33B107.7
C4—C5—C6111.7 (3)C33—C34—C38110.1 (3)
C4—C5—H5A109.3C33—C34—C39110.8 (2)
C6—C5—H5A109.3C38—C34—C39110.5 (3)
C4—C5—H5B109.3C33—C34—C35108.3 (3)
C6—C5—H5B109.3C38—C34—C35110.2 (2)
H5A—C5—H5B108.0C39—C34—C35106.9 (2)
C5—C6—C7113.3 (2)C46—C35—C30114.6 (2)
C5—C6—H6A108.9C46—C35—C34109.8 (2)
C7—C6—H6A108.9C30—C35—C34112.8 (3)
C5—C6—H6B108.9C46—C35—H35106.3
C7—C6—H6B108.9C30—C35—H35106.3
H6A—C6—H6B107.7C34—C35—H35106.3
C10—C7—C6110.6 (3)O6—C36—O5122.6 (3)
C10—C7—C11111.1 (3)O6—C36—C37126.0 (3)
C6—C7—C11110.3 (2)O5—C36—C37111.4 (3)
C10—C7—C2110.4 (2)C36—C37—H37A109.5
C6—C7—C2106.5 (2)C36—C37—H37B109.5
C11—C7—C2107.8 (2)H37A—C37—H37B109.5
O3—C8—O2123.7 (3)C36—C37—H37C109.5
O3—C8—C9125.4 (3)H37A—C37—H37C109.5
O2—C8—C9110.8 (3)H37B—C37—H37C109.5
C8—C9—H9A109.5C34—C38—H38A109.5
C8—C9—H9B109.5C34—C38—H38B109.5
H9A—C9—H9B109.5H38A—C38—H38B109.5
C8—C9—H9C109.5C34—C38—H38C109.5
H9A—C9—H9C109.5H38A—C38—H38C109.5
H9B—C9—H9C109.5H38B—C38—H38C109.5
C7—C10—H10A109.5C40—C39—C44111.4 (3)
C7—C10—H10B109.5C40—C39—C34114.5 (3)
H10A—C10—H10B109.5C44—C39—C34112.2 (2)
C7—C10—H10C109.5C40—C39—H39106.0
H10A—C10—H10C109.5C44—C39—H39106.0
H10B—C10—H10C109.5C34—C39—H39106.0
C12—C11—C16110.2 (2)C39—C40—C41113.9 (3)
C12—C11—C7113.4 (2)C39—C40—H40A108.8
C16—C11—C7113.3 (2)C41—C40—H40A108.8
C12—C11—H11106.5C39—C40—H40B108.8
C16—C11—H11106.5C41—C40—H40B108.8
C7—C11—H11106.5H40A—C40—H40B107.7
C11—C12—C13113.5 (3)C42—C41—C40111.3 (3)
C11—C12—H12A108.9C42—C41—H41A109.4
C13—C12—H12A108.9C40—C41—H41A109.4
C11—C12—H12B108.9C42—C41—H41B109.4
C13—C12—H12B108.9C40—C41—H41B109.4
H12A—C12—H12B107.7H41A—C41—H41B108.0
C14—C13—C12111.6 (2)C41—C42—C47111.3 (3)
C14—C13—H13A109.3C41—C42—C43107.0 (2)
C12—C13—H13A109.3C47—C42—C43111.8 (3)
C14—C13—H13B109.3C41—C42—C48116.8 (3)
C12—C13—H13B109.3C47—C42—C48109.9 (3)
H13A—C13—H13B108.0C43—C42—C4899.4 (2)
C13—C14—C15107.3 (2)C44—C43—C50119.1 (2)
C13—C14—C18110.6 (3)C44—C43—C42114.3 (3)
C15—C14—C18112.0 (3)C50—C43—C42103.7 (2)
C13—C14—C19116.7 (2)C44—C43—H43106.3
C15—C14—C19100.3 (2)C50—C43—H43106.3
C18—C14—C19109.6 (3)C42—C43—H43106.3
C16—C15—C21118.7 (2)C43—C44—C39110.2 (2)
C16—C15—C14113.5 (2)C43—C44—C45110.2 (3)
C21—C15—C14104.3 (2)C39—C44—C45110.4 (3)
C16—C15—H15106.5C43—C44—H44108.6
C21—C15—H15106.5C39—C44—H44108.6
C14—C15—H15106.5C45—C44—H44108.6
C15—C16—C17111.2 (2)C46—C45—C44112.6 (3)
C15—C16—C11109.1 (2)C46—C45—H45A109.1
C17—C16—C11111.9 (2)C44—C45—H45A109.1
C15—C16—H16108.2C46—C45—H45B109.1
C17—C16—H16108.2C44—C45—H45B109.1
C11—C16—H16108.2H45A—C45—H45B107.8
C1—C17—C16109.1 (3)N2—C46—C45125.6 (3)
C1—C17—H17A109.9N2—C46—C35117.9 (3)
C16—C17—H17A109.9C45—C46—C35116.5 (2)
C1—C17—H17B109.9C42—C47—H47A109.5
C16—C17—H17B109.9C42—C47—H47B109.5
H17A—C17—H17B108.3H47A—C47—H47B109.5
C14—C18—H18A109.5C42—C47—H47C109.5
C14—C18—H18B109.5H47A—C47—H47C109.5
H18A—C18—H18B109.5H47B—C47—H47C109.5
C14—C18—H18C109.5C51—C48—C49112.1 (3)
H18A—C18—H18C109.5C51—C48—C42119.6 (3)
H18B—C18—H18C109.5C49—C48—C42102.8 (2)
C22—C19—C20112.1 (3)C51—C48—H48107.2
C22—C19—C14118.3 (3)C49—C48—H48107.2
C20—C19—C14103.1 (2)C42—C48—H48107.2
C22—C19—H19107.6C50—C49—C48107.7 (3)
C20—C19—H19107.6C50—C49—H49A110.2
C14—C19—H19107.6C48—C49—H49A110.2
C21—C20—C19107.2 (2)C50—C49—H49B110.2
C21—C20—H20A110.3C48—C49—H49B110.2
C19—C20—H20A110.3H49A—C49—H49B108.5
C21—C20—H20B110.3C43—C50—C49103.3 (2)
C19—C20—H20B110.3C43—C50—H50A111.1
H20A—C20—H20B108.5C49—C50—H50A111.1
C15—C21—C20103.6 (2)C43—C50—H50B111.1
C15—C21—H21A111.0C49—C50—H50B111.1
C20—C21—H21A111.0H50A—C50—H50B109.1
C15—C21—H21B111.0C52—C51—C53109.9 (3)
C20—C21—H21B111.0C52—C51—C48113.2 (3)
H21A—C21—H21B109.0C53—C51—C48108.4 (3)
C24—C22—C23109.9 (3)C52—C51—H51108.4
C24—C22—C19110.8 (3)C53—C51—H51108.4
C23—C22—C19112.8 (3)C48—C51—H51108.4
C24—C22—H22107.7C51—C52—H52A109.5
C23—C22—H22107.7C51—C52—H52B109.5
C19—C22—H22107.7H52A—C52—H52B109.5
C22—C23—H23A109.5C51—C52—H52C109.5
C22—C23—H23B109.5H52A—C52—H52C109.5
H23A—C23—H23B109.5H52B—C52—H52C109.5
C22—C23—H23C109.5C54—C53—C51116.5 (3)
H23A—C23—H23C109.5C54—C53—H53A108.2
H23B—C23—H23C109.5C51—C53—H53A108.2
C25—C24—C22114.3 (3)C54—C53—H53B108.2
C25—C24—H24A108.7C51—C53—H53B108.2
C22—C24—H24A108.7H53A—C53—H53B107.3
C25—C24—H24B108.7C53—C54—C55113.1 (3)
C22—C24—H24B108.7C53—C54—H54A109.0
H24A—C24—H24B107.6C55—C54—H54A109.0
C24—C25—C26112.8 (3)C53—C54—H54B109.0
C24—C25—H25A109.0C55—C54—H54B109.0
C26—C25—H25A109.0H54A—C54—H54B107.8
C24—C25—H25B109.0C56—C55—C54114.0 (3)
C26—C25—H25B109.0C56—C55—H55A108.8
H25A—C25—H25B107.8C54—C55—H55A108.8
C27—C26—C25115.1 (3)C56—C55—H55B108.8
C27—C26—H26A108.5C54—C55—H55B108.8
C25—C26—H26A108.5H55A—C55—H55B107.7
C27—C26—H26B108.5C58—C56—C57110.1 (3)
C25—C26—H26B108.5C58—C56—C55110.3 (3)
H26A—C26—H26B107.5C57—C56—C55111.9 (3)
C29—C27—C26113.2 (3)C58—C56—H56108.1
C29—C27—C28110.2 (3)C57—C56—H56108.1
C26—C27—C28110.6 (3)C55—C56—H56108.1
C29—C27—H27107.5C56—C57—H57A109.5
C26—C27—H27107.5C56—C57—H57B109.5
C28—C27—H27107.5H57A—C57—H57B109.5
C27—C28—H28A109.5C56—C57—H57C109.5
C27—C28—H28B109.5H57A—C57—H57C109.5
H28A—C28—H28B109.5H57B—C57—H57C109.5
C27—C28—H28C109.5C56—C58—H58A109.5
H28A—C28—H28C109.5C56—C58—H58B109.5
H28B—C28—H28C109.5H58A—C58—H58B109.5
C27—C29—H29A109.5C56—C58—H58C109.5
C27—C29—H29B109.5H58A—C58—H58C109.5
H29A—C29—H29B109.5H58B—C58—H58C109.5
O1—N1—C1—C17−1.5 (4)C36—O5—C31—C32156.6 (3)
O1—N1—C1—C2−179.0 (2)C36—O5—C31—C30−81.7 (3)
N1—C1—C2—C3−11.2 (4)C35—C30—C31—O5−175.1 (3)
C17—C1—C2—C3171.0 (3)C35—C30—C31—C32−56.5 (4)
N1—C1—C2—C7117.3 (3)O5—C31—C32—C33177.2 (2)
C17—C1—C2—C7−60.5 (3)C30—C31—C32—C3356.3 (3)
C1—C2—C3—C4−174.8 (3)C31—C32—C33—C34−56.0 (4)
C7—C2—C3—C458.6 (4)C32—C33—C34—C38−66.9 (3)
C8—O2—C4—C3−158.8 (3)C32—C33—C34—C39170.5 (3)
C8—O2—C4—C580.7 (3)C32—C33—C34—C3553.6 (3)
C2—C3—C4—O2−174.7 (2)C31—C30—C35—C46−177.3 (3)
C2—C3—C4—C5−55.9 (3)C31—C30—C35—C3456.1 (4)
O2—C4—C5—C6171.0 (3)C33—C34—C35—C46177.0 (3)
C3—C4—C5—C654.6 (4)C38—C34—C35—C46−62.5 (3)
C4—C5—C6—C7−55.3 (4)C39—C34—C35—C4657.6 (3)
C5—C6—C7—C10−65.6 (3)C33—C34—C35—C30−53.9 (3)
C5—C6—C7—C11171.1 (3)C38—C34—C35—C3066.6 (3)
C5—C6—C7—C254.3 (3)C39—C34—C35—C30−173.2 (2)
C1—C2—C7—C10−65.9 (3)C31—O5—C36—O6−2.6 (4)
C3—C2—C7—C1063.4 (3)C31—O5—C36—C37178.0 (3)
C1—C2—C7—C6174.0 (2)C33—C34—C39—C4052.2 (4)
C3—C2—C7—C6−56.7 (3)C38—C34—C39—C40−70.1 (3)
C1—C2—C7—C1155.6 (3)C35—C34—C39—C40169.9 (3)
C3—C2—C7—C11−175.1 (2)C33—C34—C39—C44−179.7 (3)
C4—O2—C8—O33.8 (5)C38—C34—C39—C4458.0 (3)
C4—O2—C8—C9−175.1 (3)C35—C34—C39—C44−61.9 (3)
C10—C7—C11—C12−59.8 (3)C44—C39—C40—C4152.1 (4)
C6—C7—C11—C1263.1 (3)C34—C39—C40—C41−179.3 (3)
C2—C7—C11—C12179.1 (3)C39—C40—C41—C42−55.7 (4)
C10—C7—C11—C1666.7 (3)C40—C41—C42—C47−66.6 (3)
C6—C7—C11—C16−170.3 (3)C40—C41—C42—C4355.8 (4)
C2—C7—C11—C16−54.4 (3)C40—C41—C42—C48166.0 (3)
C16—C11—C12—C1352.9 (3)C41—C42—C43—C44−58.7 (3)
C7—C11—C12—C13−178.9 (3)C47—C42—C43—C4463.4 (4)
C11—C12—C13—C14−54.6 (4)C48—C42—C43—C44179.4 (3)
C12—C13—C14—C1555.3 (3)C41—C42—C43—C50170.1 (3)
C12—C13—C14—C18−67.1 (3)C47—C42—C43—C50−67.9 (3)
C12—C13—C14—C19166.8 (3)C48—C42—C43—C5048.2 (3)
C13—C14—C15—C16−60.4 (3)C50—C43—C44—C39−179.9 (3)
C18—C14—C15—C1661.1 (3)C42—C43—C44—C3956.8 (3)
C19—C14—C15—C16177.2 (2)C50—C43—C44—C45−57.7 (4)
C13—C14—C15—C21169.0 (2)C42—C43—C44—C45179.0 (3)
C18—C14—C15—C21−69.5 (3)C40—C39—C44—C43−51.1 (4)
C19—C14—C15—C2146.6 (3)C34—C39—C44—C43179.1 (3)
C21—C15—C16—C17−52.5 (4)C40—C39—C44—C45−173.1 (3)
C14—C15—C16—C17−175.6 (3)C34—C39—C44—C4557.1 (3)
C21—C15—C16—C11−176.4 (3)C43—C44—C45—C46−169.9 (3)
C14—C15—C16—C1160.5 (3)C39—C44—C45—C46−47.9 (4)
C12—C11—C16—C15−54.2 (3)O4—N2—C46—C451.4 (5)
C7—C11—C16—C15177.6 (3)O4—N2—C46—C35−179.9 (3)
C12—C11—C16—C17−177.7 (3)C44—C45—C46—N2−133.0 (3)
C7—C11—C16—C1754.1 (3)C44—C45—C46—C3548.3 (4)
N1—C1—C17—C16−119.9 (3)C30—C35—C46—N2−0.7 (4)
C2—C1—C17—C1657.7 (4)C34—C35—C46—N2127.5 (3)
C15—C16—C17—C1−174.7 (3)C30—C35—C46—C45178.2 (3)
C11—C16—C17—C1−52.4 (3)C34—C35—C46—C45−53.7 (4)
C13—C14—C19—C2280.5 (4)C41—C42—C48—C5180.1 (4)
C15—C14—C19—C22−164.0 (3)C47—C42—C48—C51−47.8 (4)
C18—C14—C19—C22−46.1 (4)C43—C42—C48—C51−165.3 (3)
C13—C14—C19—C20−155.1 (3)C41—C42—C48—C49−155.0 (3)
C15—C14—C19—C20−39.7 (3)C47—C42—C48—C4977.1 (3)
C18—C14—C19—C2078.3 (3)C43—C42—C48—C49−40.4 (3)
C22—C19—C20—C21147.6 (3)C51—C48—C49—C50148.8 (3)
C14—C19—C20—C2119.3 (3)C42—C48—C49—C5019.1 (3)
C16—C15—C21—C20−162.2 (3)C44—C43—C50—C49−165.0 (3)
C14—C15—C21—C20−34.7 (3)C42—C43—C50—C49−36.6 (3)
C19—C20—C21—C159.0 (4)C48—C49—C50—C4310.3 (4)
C20—C19—C22—C2455.8 (3)C49—C48—C51—C52−176.2 (3)
C14—C19—C22—C24175.6 (3)C42—C48—C51—C52−55.8 (4)
C20—C19—C22—C23179.5 (3)C49—C48—C51—C5361.6 (4)
C14—C19—C22—C23−60.6 (4)C42—C48—C51—C53−178.1 (3)
C23—C22—C24—C2573.6 (4)C52—C51—C53—C5464.8 (4)
C19—C22—C24—C25−161.0 (3)C48—C51—C53—C54−171.0 (3)
C22—C24—C25—C26168.9 (3)C51—C53—C54—C5565.8 (4)
C24—C25—C26—C27−167.5 (3)C53—C54—C55—C56165.0 (3)
C25—C26—C27—C29−65.6 (4)C54—C55—C56—C58168.9 (3)
C25—C26—C27—C28170.2 (3)C54—C55—C56—C57−68.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.98 (4)1.88 (4)2.809 (3)157 (4)
O4—H4···N10.95 (4)1.82 (4)2.733 (3)160 (3)
C9—H9c···O6i0.982.583.404 (4)142
C37—H37c···O3ii0.982.403.373 (4)169
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y−1/2, −z+1.

Experimental details

Crystal data
Chemical formulaC29H49NO3
Mr459.69
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)11.3934 (13), 9.6588 (11), 25.018 (3)
β (°) 93.466 (2)
V (Å3)2748.1 (5)
Z4
Radiation typeMo Kα
µ (mm−1)0.07
Crystal size (mm)0.35 × 0.30 × 0.03
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.757, 0.862
No. of measured, independent and
observed [I > 2σ(I)] reflections		26531, 6690, 4553
Rint0.086
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.114, 0.99
No. of reflections6690
No. of parameters615
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.24, −0.23
Absolute structureNd

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···N20.98 (4)1.88 (4)2.809 (3)157 (4)
O4—H4···N10.95 (4)1.82 (4)2.733 (3)160 (3)
C9—H9c···O6i0.982.583.404 (4)142
C37—H37c···O3ii0.982.403.373 (4)169
Symmetry codes: (i) x+1, y, z; (ii) −x+2, y−1/2, −z+1.
 

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 citationAnagnostopoulos, C. E. & Fieser, L. F. (1954). J. Am. Chem. Soc. 76, 532–536.  CrossRef CAS Web of Science Google Scholar
 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 citationChoucair, B., Dherbomez, M., Roussakis, C. & Kihel, L. El. (2004). Tetrahedron Lett. 60, 11477–11486.  CrossRef CAS Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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 First citationKetuly, K. A. & A. Hadi, A. H. (2010). Molecules, 15, 2347–2356.  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 citationPetersen, Q. R. (1963). Proc. Indiana Acad. Sci. 73, 127–131.  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
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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 4| April 2011| Pages o773-o774
doi:10.1107/S1600536811007306
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