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

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ISSN: 2056-9890

4,4,6a,6b,11,12,14b-Hepta­methyl-16-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,9,10,11,12,12a,14a,14b-octa­deca­hydro-12b,8a-(ep­oxy­methano)­picen-3-yl acetate

aUniversity of Peshawar, Institute of Chemical Sciences, Peshawar 25120, Pakistan, bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, cUniversity of Peshawar, Centre of Biotechnology and Microbiology, Peshawar 25120, Pakistan, and dQuaid-i-Azam University, Department of Chemistry, Islamabad, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 13 March 2013; accepted 16 March 2013; online 23 March 2013)

The title compound, C32H48O4, which was extracted from the bark of Rhododendron arboreum, consists of five fused rings to which an acetate and seven methyl groups are attached. The A, D and E rings adopt chair conformations, the B ring is in a distorted chair and the C ring is in a half-chair conformation. The five-membered ring formed by the lactone group, which bridges from the A/B to the B/C ring junctions, is an approximate envelope with the C atom of the methyne group as the flap [displacement from the other four atoms = 0.753 (2) Å]. There are no identified directional inter­actions in the crystal structure.

Related literature

For a related crystal structure, see: El-Seedi et al. (1994[El-Seedi, H. R., Hazell, A. C. & Torssell, K. B. G. (1994). Phytochemistry, 35, 1297-1299.]). For puckering parameters, see: Cremer & Pople (1975)[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.].

[Scheme 1]

Experimental

Crystal data
  • C32H48O4

  • Mr = 496.70

  • Monoclinic, P 21

  • a = 13.7309 (8) Å

  • b = 6.9177 (4) Å

  • c = 14.8539 (9) Å

  • β = 90.943 (2)°

  • V = 1410.73 (14) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.35 × 0.20 × 0.18 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.987

  • 11401 measured reflections

  • 2856 independent reflections

  • 2261 reflections with I > 2σ(I)

  • Rint = 0.029

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.101

  • S = 1.03

  • 2856 reflections

  • 333 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.15 e Å−3

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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.

Supporting information


Comment top

The title compound (I), (Fig. 1) has been extracted from the bark of Rhododendron arboreum collected in February 2011 from Butal, Hazar division, Pakistan.

The crystal structures of 3β,13β-13,28-Epoxy-3-acetoxy-11oleanene (El-Seedi et al., 1994) extracted from the bark of Minquartia guianensis has been published which is related to (I).

In (I), five six-membered rings A (C2–C7), B (C5/C6/C9—C12), C (C9/C10/C15—C18), D (C15/C16/C20—C23) and E (C22/C23/C25—C28) are fused to each other. Seven methyl groups are attached at different positions. A carboxylate group is fused over ring A & B. One acetate group is also attached at the terminal ring E. The rings A, B, C, D and E are confirmed by different puckering parameters (Cremer & Pople, 1975). The puckering amplitude Q for rings A, B, C, D and E have values of 0.558 (3), 0.623 (3), 0.557 (3), 0.574 (3) & 0.561 (3) Å, θ for rings A, B, C, D and E have values of 3.6 (3), 164.3 (3), 49.3 (3), 172.3 (3) & 2.7 (3)°, ϕ for rings A, B, C, D and E have values of 323 (5), 230.3 (9), 102.6 (4), 359 (2) & 184 (7)°, respectively. The acetate group F (O3/O4/C31/C32) is planar with r. m. s. deviation of 0.0021 Å. It is oriented at a dihedral angle of 72.36 (0.15) ° with the plane of (C22/C25/C26/C28).

Related literature top

For a related crystal structure, see: El-Seedi et al. (1994). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The dried and crushed barks of Rhododendron arboreum (5 kg) were subjected to cold extraction with methanol (MeOH). The MeOH extract (0.3 kg) was suspended in water and successively partitioned with n-hexane, CHCl3, EtOAc and butanol (BuOH). The CHCl3 fraction (15 g) was subjected to column chromatography on silica gel. The column was first eluted with n-hexane: CHCL3 (100:0 0:100) as solvent system. A total of 23 fractions, SF-1 to SF-23 were obtained based on TLC profiles. On further purification of fraction SF18 through pencil column colourless needles of (I) were obtained. Yield: 10 mg.

Refinement top

Anomanous dispersion was negligible and the absolute structure of (I) is indeterminate based on the present refinement. The H-atoms were positioned geometrically at C—H = 0.96—0.98 Å and included in the refinement as riding with Uiso(H) = xUeq(C), where x = 1.5 for metyl H-atoms and x = 1.2 for all other H-atoms.

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 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
4,4,6a,6b,11,12,14b-Heptamethyl-16-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,9,10,11,12,12a,14a,14b-octadecahydro-12b,8a-(epoxymethano)picen-3-yl acetate top
Crystal data top
C32H48O4F(000) = 544
Mr = 496.70Dx = 1.169 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2261 reflections
a = 13.7309 (8) Åθ = 2.7–25.3°
b = 6.9177 (4) ŵ = 0.08 mm1
c = 14.8539 (9) ÅT = 296 K
β = 90.943 (2)°Needle, colorless
V = 1410.73 (14) Å30.35 × 0.20 × 0.18 mm
Z = 2
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2856 independent reflections
Radiation source: fine-focus sealed tube2261 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: 8.10 pixels mm-1θmax = 25.5°, θmin = 2.7°
ω scansh = 1516
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 85
Tmin = 0.975, Tmax = 0.987l = 1717
11401 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0488P)2 + 0.1608P]
where P = (Fo2 + 2Fc2)/3
2856 reflections(Δ/σ)max < 0.001
333 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.15 e Å3
Crystal data top
C32H48O4V = 1410.73 (14) Å3
Mr = 496.70Z = 2
Monoclinic, P21Mo Kα radiation
a = 13.7309 (8) ŵ = 0.08 mm1
b = 6.9177 (4) ÅT = 296 K
c = 14.8539 (9) Å0.35 × 0.20 × 0.18 mm
β = 90.943 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2856 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2261 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.987Rint = 0.029
11401 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0411 restraint
wR(F2) = 0.101H-atom parameters constrained
S = 1.03Δρmax = 0.15 e Å3
2856 reflectionsΔρmin = 0.15 e Å3
333 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O10.32780 (13)0.9669 (3)0.29373 (12)0.0464 (6)
O20.45050 (16)1.0954 (3)0.21754 (15)0.0664 (8)
O30.05842 (19)0.5882 (4)0.84926 (15)0.0817 (10)
O40.0088 (2)0.2830 (5)0.83569 (19)0.1098 (14)
C10.2961 (3)0.2682 (6)0.0396 (2)0.0783 (14)
C20.3127 (2)0.4699 (5)0.08018 (18)0.0571 (10)
C30.4184 (2)0.5303 (5)0.0680 (2)0.0641 (11)
C40.4413 (2)0.7319 (5)0.1039 (2)0.0610 (11)
C50.40994 (19)0.7503 (4)0.20146 (18)0.0450 (9)
C60.30424 (18)0.6838 (4)0.21412 (16)0.0407 (8)
C70.2829 (2)0.4786 (4)0.18059 (18)0.0478 (9)
C80.1764 (2)0.4236 (6)0.1928 (2)0.0706 (12)
C90.28636 (17)0.7675 (4)0.30996 (16)0.0374 (8)
C100.34669 (17)0.6733 (4)0.38810 (16)0.0349 (8)
C110.45584 (18)0.6933 (4)0.36732 (17)0.0457 (9)
C120.47923 (19)0.6465 (4)0.26904 (18)0.0495 (10)
C130.4016 (2)0.9561 (4)0.23483 (18)0.0488 (9)
C140.3239 (2)0.4550 (4)0.39160 (17)0.0442 (8)
C150.31827 (17)0.7735 (4)0.48074 (16)0.0357 (8)
C160.20947 (17)0.7223 (3)0.49750 (16)0.0383 (8)
C170.14878 (18)0.7802 (5)0.41643 (18)0.0462 (9)
C180.18247 (18)0.7978 (4)0.33399 (18)0.0463 (9)
C190.3337 (2)0.9951 (3)0.47758 (18)0.0441 (9)
C200.38119 (18)0.6971 (4)0.56019 (17)0.0454 (9)
C210.34095 (18)0.7519 (5)0.65228 (17)0.0495 (10)
C220.23627 (19)0.6818 (4)0.66293 (18)0.0456 (9)
C230.16692 (18)0.7774 (4)0.59105 (18)0.0423 (8)
C240.1520 (2)0.9982 (4)0.6012 (2)0.0558 (11)
C250.0663 (2)0.6807 (5)0.59872 (19)0.0583 (10)
C260.0281 (2)0.6833 (6)0.6953 (2)0.0675 (11)
C270.0994 (3)0.5862 (5)0.7590 (2)0.0655 (11)
C280.2011 (2)0.6766 (5)0.76271 (19)0.0574 (11)
C290.2007 (3)0.8748 (6)0.8091 (2)0.0770 (16)
C300.2685 (3)0.5399 (7)0.8174 (2)0.0900 (16)
C310.0121 (3)0.4303 (7)0.8771 (2)0.0742 (14)
C320.0336 (3)0.4631 (8)0.9671 (2)0.1036 (19)
H1A0.315780.268190.022160.1174*
H1B0.228300.235530.042610.1174*
H1C0.333880.174900.072830.1174*
H20.271510.561300.046540.0684*
H3A0.433180.526030.004420.0769*
H3B0.460320.437640.098630.0769*
H4A0.510650.756150.100030.0733*
H4B0.407420.827640.067370.0733*
H60.265830.767210.173750.0488*
H70.323700.387880.215070.0573*
H8A0.135900.504370.155190.1061*
H8B0.159160.441180.254590.1061*
H8C0.166970.290770.176100.1061*
H11A0.476500.824430.380580.0548*
H11B0.492750.607050.406470.0548*
H12A0.474380.507970.259860.0595*
H12B0.545790.684670.257240.0595*
H14A0.362350.388340.347980.0662*
H14B0.256050.434550.378340.0662*
H14C0.339270.406160.450650.0662*
H160.207950.580660.496760.0460*
H170.083050.805360.425020.0554*
H180.138670.831090.288150.0555*
H19A0.335211.045670.537780.0661*
H19B0.281121.053910.444090.0661*
H19C0.394201.023190.448920.0661*
H20A0.385260.557360.556080.0545*
H20B0.446640.748320.555290.0545*
H21A0.381730.695370.699280.0594*
H21B0.343040.891250.659220.0594*
H220.238490.545470.645170.0547*
H24A0.137171.053590.543330.0837*
H24B0.210511.055550.625330.0837*
H24C0.099181.022180.641200.0837*
H25A0.020150.747300.559460.0699*
H25B0.070700.547850.578350.0699*
H26A0.017950.815920.714180.0809*
H26B0.034060.616800.697080.0809*
H270.106200.451160.740240.0784*
H29A0.148810.952200.784180.1155*
H29B0.261800.938330.799660.1155*
H29C0.191060.857940.872490.1155*
H30A0.240310.514640.874950.1345*
H30B0.331060.599590.825950.1345*
H30C0.275900.420510.785300.1345*
H32A0.065800.347030.985920.1552*
H32B0.080180.566180.962360.1552*
H32C0.016020.496871.010630.1552*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0564 (11)0.0303 (9)0.0526 (11)0.0062 (9)0.0044 (9)0.0073 (8)
O20.0744 (15)0.0429 (12)0.0820 (16)0.0120 (11)0.0050 (12)0.0171 (11)
O30.112 (2)0.0720 (17)0.0624 (14)0.0162 (15)0.0373 (13)0.0018 (12)
O40.150 (3)0.095 (2)0.085 (2)0.049 (2)0.0222 (18)0.0005 (19)
C10.109 (3)0.069 (2)0.057 (2)0.005 (2)0.0036 (19)0.0152 (18)
C20.074 (2)0.0529 (17)0.0445 (16)0.0090 (17)0.0024 (14)0.0008 (14)
C30.078 (2)0.061 (2)0.0540 (19)0.0142 (18)0.0183 (16)0.0011 (15)
C40.063 (2)0.062 (2)0.0585 (19)0.0050 (16)0.0183 (15)0.0111 (15)
C50.0459 (16)0.0402 (15)0.0493 (16)0.0042 (13)0.0102 (12)0.0075 (12)
C60.0441 (15)0.0396 (14)0.0383 (14)0.0060 (12)0.0017 (11)0.0068 (12)
C70.0563 (17)0.0407 (15)0.0463 (15)0.0001 (14)0.0018 (12)0.0007 (12)
C80.066 (2)0.078 (2)0.068 (2)0.0183 (18)0.0033 (16)0.0197 (18)
C90.0390 (14)0.0291 (12)0.0440 (15)0.0047 (11)0.0012 (11)0.0036 (11)
C100.0314 (13)0.0286 (12)0.0445 (14)0.0015 (11)0.0006 (11)0.0063 (11)
C110.0377 (15)0.0431 (15)0.0562 (17)0.0047 (12)0.0002 (12)0.0073 (13)
C120.0388 (15)0.0467 (17)0.0634 (18)0.0045 (13)0.0098 (13)0.0090 (14)
C130.0556 (18)0.0392 (15)0.0516 (16)0.0006 (14)0.0035 (14)0.0118 (13)
C140.0547 (16)0.0307 (13)0.0472 (15)0.0032 (13)0.0022 (12)0.0043 (12)
C150.0351 (13)0.0267 (12)0.0451 (14)0.0007 (11)0.0040 (11)0.0042 (11)
C160.0363 (14)0.0322 (14)0.0463 (15)0.0022 (10)0.0036 (11)0.0001 (11)
C170.0311 (13)0.0579 (17)0.0494 (17)0.0049 (14)0.0014 (12)0.0036 (14)
C180.0381 (14)0.0522 (17)0.0482 (17)0.0115 (13)0.0092 (12)0.0003 (13)
C190.0490 (16)0.0301 (14)0.0532 (16)0.0053 (12)0.0006 (12)0.0002 (12)
C200.0398 (15)0.0444 (15)0.0518 (16)0.0001 (12)0.0077 (12)0.0063 (13)
C210.0487 (16)0.0545 (18)0.0449 (16)0.0017 (14)0.0116 (12)0.0038 (13)
C220.0516 (16)0.0370 (14)0.0482 (15)0.0017 (13)0.0006 (12)0.0019 (12)
C230.0407 (15)0.0401 (14)0.0460 (15)0.0014 (13)0.0016 (12)0.0018 (12)
C240.0584 (18)0.0503 (19)0.0589 (18)0.0133 (15)0.0042 (14)0.0026 (14)
C250.0456 (16)0.075 (2)0.0546 (18)0.0080 (16)0.0097 (13)0.0088 (16)
C260.0585 (19)0.083 (2)0.0615 (19)0.0168 (19)0.0159 (16)0.0089 (18)
C270.086 (2)0.058 (2)0.0533 (19)0.0095 (19)0.0227 (17)0.0043 (16)
C280.070 (2)0.0596 (19)0.0428 (16)0.0005 (17)0.0050 (14)0.0030 (15)
C290.095 (3)0.080 (3)0.056 (2)0.015 (2)0.0053 (18)0.0143 (19)
C300.105 (3)0.108 (3)0.057 (2)0.019 (3)0.0047 (19)0.027 (2)
C310.080 (2)0.085 (3)0.058 (2)0.010 (2)0.0121 (18)0.015 (2)
C320.119 (3)0.118 (4)0.075 (3)0.002 (3)0.038 (2)0.023 (3)
Geometric parameters (Å, º) top
O1—C91.513 (3)C3—H3A0.9700
O1—C131.352 (3)C3—H3B0.9700
O2—C131.205 (3)C4—H4A0.9700
O3—C271.463 (4)C4—H4B0.9700
O3—C311.333 (5)C6—H60.9800
O4—C311.191 (6)C7—H70.9800
C1—C21.536 (5)C8—H8A0.9600
C2—C31.524 (4)C8—H8B0.9600
C2—C71.554 (4)C8—H8C0.9600
C3—C41.524 (5)C11—H11A0.9700
C4—C51.524 (4)C11—H11B0.9700
C5—C61.537 (4)C12—H12A0.9700
C5—C121.548 (4)C12—H12B0.9700
C5—C131.512 (4)C14—H14A0.9600
C6—C71.531 (4)C14—H14B0.9600
C6—C91.560 (3)C14—H14C0.9600
C7—C81.525 (4)C16—H160.9800
C9—C101.558 (3)C17—H170.9300
C9—C181.491 (3)C18—H180.9300
C10—C111.541 (3)C19—H19A0.9600
C10—C141.543 (4)C19—H19B0.9600
C10—C151.595 (3)C19—H19C0.9600
C11—C121.534 (4)C20—H20A0.9700
C15—C161.559 (3)C20—H20B0.9700
C15—C191.548 (3)C21—H21A0.9700
C15—C201.544 (4)C21—H21B0.9700
C16—C171.507 (4)C22—H220.9800
C16—C231.563 (4)C24—H24A0.9600
C17—C181.322 (4)C24—H24B0.9600
C20—C211.531 (4)C24—H24C0.9600
C21—C221.528 (4)C25—H25A0.9700
C22—C231.565 (4)C25—H25B0.9700
C22—C281.567 (4)C26—H26A0.9700
C23—C241.549 (4)C26—H26B0.9700
C23—C251.541 (4)C27—H270.9800
C25—C261.536 (4)C29—H29A0.9600
C26—C271.508 (5)C29—H29B0.9600
C27—C281.530 (5)C29—H29C0.9600
C28—C291.535 (5)C30—H30A0.9600
C28—C301.545 (5)C30—H30B0.9600
C31—C321.503 (5)C30—H30C0.9600
C1—H1A0.9600C32—H32A0.9600
C1—H1B0.9600C32—H32B0.9600
C1—H1C0.9600C32—H32C0.9600
C2—H20.9800
C9—O1—C13109.9 (2)C5—C6—H6104.00
C27—O3—C31118.0 (3)C7—C6—H6104.00
C1—C2—C3109.8 (3)C9—C6—H6104.00
C1—C2—C7111.9 (3)C2—C7—H7109.00
C3—C2—C7111.7 (2)C6—C7—H7109.00
C2—C3—C4113.6 (3)C8—C7—H7109.00
C3—C4—C5110.4 (2)C7—C8—H8A109.00
C4—C5—C6111.9 (2)C7—C8—H8B110.00
C4—C5—C12113.4 (2)C7—C8—H8C109.00
C4—C5—C13114.5 (2)H8A—C8—H8B109.00
C6—C5—C12110.7 (2)H8A—C8—H8C109.00
C6—C5—C1399.5 (2)H8B—C8—H8C110.00
C12—C5—C13105.9 (2)C10—C11—H11A109.00
C5—C6—C7114.4 (2)C10—C11—H11B109.00
C5—C6—C999.4 (2)C12—C11—H11A109.00
C7—C6—C9127.5 (2)C12—C11—H11B109.00
C2—C7—C6107.2 (2)H11A—C11—H11B108.00
C2—C7—C8111.9 (2)C5—C12—H12A109.00
C6—C7—C8111.8 (2)C5—C12—H12B109.00
O1—C9—C697.34 (18)C11—C12—H12A109.00
O1—C9—C10107.66 (19)C11—C12—H12B109.00
O1—C9—C18105.9 (2)H12A—C12—H12B108.00
C6—C9—C10115.8 (2)C10—C14—H14A109.00
C6—C9—C18115.9 (2)C10—C14—H14B110.00
C10—C9—C18112.3 (2)C10—C14—H14C109.00
C9—C10—C11108.7 (2)H14A—C14—H14B109.00
C9—C10—C14109.2 (2)H14A—C14—H14C109.00
C9—C10—C15109.1 (2)H14B—C14—H14C109.00
C11—C10—C14107.0 (2)C15—C16—H16104.00
C11—C10—C15112.7 (2)C17—C16—H16104.00
C14—C10—C15110.1 (2)C23—C16—H16104.00
C10—C11—C12113.0 (2)C16—C17—H17118.00
C5—C12—C11112.5 (2)C18—C17—H17118.00
O1—C13—O2121.4 (3)C9—C18—H18118.00
O1—C13—C5109.0 (2)C17—C18—H18118.00
O2—C13—C5129.6 (3)C15—C19—H19A109.00
C10—C15—C16106.72 (19)C15—C19—H19B109.00
C10—C15—C19111.6 (2)C15—C19—H19C110.00
C10—C15—C20111.6 (2)H19A—C19—H19B109.00
C16—C15—C19111.2 (2)H19A—C19—H19C110.00
C16—C15—C20109.0 (2)H19B—C19—H19C109.00
C19—C15—C20106.7 (2)C15—C20—H20A109.00
C15—C16—C17109.3 (2)C15—C20—H20B109.00
C15—C16—C23117.36 (19)C21—C20—H20A109.00
C17—C16—C23115.8 (2)C21—C20—H20B109.00
C16—C17—C18124.6 (2)H20A—C20—H20B108.00
C9—C18—C17124.0 (2)C20—C21—H21A109.00
C15—C20—C21113.1 (2)C20—C21—H21B109.00
C20—C21—C22111.6 (2)C22—C21—H21A109.00
C21—C22—C23111.0 (2)C22—C21—H21B109.00
C21—C22—C28114.2 (2)H21A—C21—H21B108.00
C23—C22—C28117.5 (2)C21—C22—H22104.00
C16—C23—C22105.7 (2)C23—C22—H22104.00
C16—C23—C24112.3 (2)C28—C22—H22104.00
C16—C23—C25108.0 (2)C23—C24—H24A109.00
C22—C23—C24115.5 (2)C23—C24—H24B109.00
C22—C23—C25107.6 (2)C23—C24—H24C109.00
C24—C23—C25107.5 (2)H24A—C24—H24B109.00
C23—C25—C26112.6 (2)H24A—C24—H24C110.00
C25—C26—C27110.7 (3)H24B—C24—H24C109.00
O3—C27—C26108.4 (3)C23—C25—H25A109.00
O3—C27—C28109.1 (3)C23—C25—H25B109.00
C26—C27—C28115.0 (3)C26—C25—H25A109.00
C22—C28—C27105.7 (2)C26—C25—H25B109.00
C22—C28—C29114.1 (3)H25A—C25—H25B108.00
C22—C28—C30108.7 (2)C25—C26—H26A110.00
C27—C28—C29111.8 (3)C25—C26—H26B110.00
C27—C28—C30107.9 (3)C27—C26—H26A110.00
C29—C28—C30108.5 (3)C27—C26—H26B110.00
O3—C31—O4123.7 (3)H26A—C26—H26B108.00
O3—C31—C32111.1 (4)O3—C27—H27108.00
O4—C31—C32125.1 (4)C26—C27—H27108.00
C2—C1—H1A109.00C28—C27—H27108.00
C2—C1—H1B109.00C28—C29—H29A109.00
C2—C1—H1C109.00C28—C29—H29B110.00
H1A—C1—H1B109.00C28—C29—H29C109.00
H1A—C1—H1C109.00H29A—C29—H29B109.00
H1B—C1—H1C110.00H29A—C29—H29C109.00
C1—C2—H2108.00H29B—C29—H29C110.00
C3—C2—H2108.00C28—C30—H30A109.00
C7—C2—H2108.00C28—C30—H30B109.00
C2—C3—H3A109.00C28—C30—H30C109.00
C2—C3—H3B109.00H30A—C30—H30B109.00
C4—C3—H3A109.00H30A—C30—H30C109.00
C4—C3—H3B109.00H30B—C30—H30C110.00
H3A—C3—H3B108.00C31—C32—H32A109.00
C3—C4—H4A110.00C31—C32—H32B110.00
C3—C4—H4B110.00C31—C32—H32C109.00
C5—C4—H4A110.00H32A—C32—H32B109.00
C5—C4—H4B110.00H32A—C32—H32C109.00
H4A—C4—H4B108.00H32B—C32—H32C109.00
C13—O1—C9—C632.6 (2)C14—C10—C11—C1274.0 (3)
C13—O1—C9—C1087.5 (2)C15—C10—C11—C12164.9 (2)
C13—O1—C9—C18152.2 (2)C9—C10—C15—C1665.3 (2)
C9—O1—C13—O2174.0 (2)C9—C10—C15—C1956.4 (3)
C9—O1—C13—C54.4 (3)C9—C10—C15—C20175.7 (2)
C31—O3—C27—C2697.1 (4)C11—C10—C15—C16174.0 (2)
C31—O3—C27—C28136.9 (3)C11—C10—C15—C1964.3 (3)
C27—O3—C31—O46.1 (6)C11—C10—C15—C2055.0 (3)
C27—O3—C31—C32174.5 (3)C14—C10—C15—C1654.5 (2)
C1—C2—C3—C4178.3 (2)C14—C10—C15—C19176.2 (2)
C7—C2—C3—C457.0 (3)C14—C10—C15—C2064.5 (3)
C1—C2—C7—C6179.0 (2)C10—C11—C12—C548.1 (3)
C1—C2—C7—C858.1 (3)C10—C15—C16—C1754.2 (3)
C3—C2—C7—C655.5 (3)C10—C15—C16—C23171.3 (2)
C3—C2—C7—C8178.4 (3)C19—C15—C16—C1767.8 (3)
C2—C3—C4—C553.2 (3)C19—C15—C16—C2366.7 (3)
C3—C4—C5—C650.6 (3)C20—C15—C16—C17174.9 (2)
C3—C4—C5—C1275.5 (3)C20—C15—C16—C2350.6 (3)
C3—C4—C5—C13162.9 (2)C10—C15—C20—C21166.3 (2)
C4—C5—C6—C754.9 (3)C16—C15—C20—C2148.6 (3)
C4—C5—C6—C9166.2 (2)C19—C15—C20—C2171.5 (3)
C12—C5—C6—C772.7 (3)C15—C16—C17—C1824.5 (4)
C12—C5—C6—C966.2 (3)C23—C16—C17—C18159.8 (3)
C13—C5—C6—C7176.2 (2)C15—C16—C23—C2254.8 (3)
C13—C5—C6—C944.9 (2)C15—C16—C23—C2472.0 (3)
C4—C5—C12—C11170.9 (2)C15—C16—C23—C25169.7 (2)
C6—C5—C12—C1162.3 (3)C17—C16—C23—C22173.7 (2)
C13—C5—C12—C1144.6 (3)C17—C16—C23—C2459.6 (3)
C4—C5—C13—O1145.8 (2)C17—C16—C23—C2558.7 (3)
C4—C5—C13—O236.0 (4)C16—C17—C18—C91.6 (5)
C6—C5—C13—O126.3 (3)C15—C20—C21—C2256.5 (3)
C6—C5—C13—O2155.5 (3)C20—C21—C22—C2361.7 (3)
C12—C5—C13—O188.5 (2)C20—C21—C22—C28162.7 (2)
C12—C5—C13—O289.7 (3)C21—C22—C23—C1657.9 (3)
C5—C6—C7—C255.5 (3)C21—C22—C23—C2466.9 (3)
C5—C6—C7—C8178.5 (2)C21—C22—C23—C25173.1 (2)
C9—C6—C7—C2179.4 (2)C28—C22—C23—C16168.1 (2)
C9—C6—C7—C856.4 (3)C28—C22—C23—C2467.1 (3)
C5—C6—C9—O146.7 (2)C28—C22—C23—C2552.9 (3)
C5—C6—C9—C1067.0 (3)C21—C22—C28—C27175.0 (3)
C5—C6—C9—C18158.3 (2)C21—C22—C28—C2961.8 (3)
C7—C6—C9—O1177.7 (2)C21—C22—C28—C3059.4 (4)
C7—C6—C9—C1064.0 (3)C23—C22—C28—C2752.4 (3)
C7—C6—C9—C1870.7 (3)C23—C22—C28—C2970.8 (3)
O1—C9—C10—C1150.0 (3)C23—C22—C28—C30168.0 (3)
O1—C9—C10—C14166.42 (19)C16—C23—C25—C26166.3 (3)
O1—C9—C10—C1573.2 (2)C22—C23—C25—C2652.6 (3)
C6—C9—C10—C1157.6 (3)C24—C23—C25—C2672.4 (3)
C6—C9—C10—C1458.8 (3)C23—C25—C26—C2757.1 (4)
C6—C9—C10—C15179.2 (2)C25—C26—C27—O3178.5 (3)
C18—C9—C10—C11166.2 (2)C25—C26—C27—C2859.0 (4)
C18—C9—C10—C1477.4 (3)O3—C27—C28—C22176.2 (2)
C18—C9—C10—C1542.9 (3)O3—C27—C28—C2951.5 (3)
O1—C9—C18—C17105.8 (3)O3—C27—C28—C3067.7 (3)
C6—C9—C18—C17147.6 (3)C26—C27—C28—C2254.1 (3)
C10—C9—C18—C1711.5 (4)C26—C27—C28—C2970.5 (3)
C9—C10—C11—C1243.9 (3)C26—C27—C28—C30170.2 (3)

Experimental details

Crystal data
Chemical formulaC32H48O4
Mr496.70
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)13.7309 (8), 6.9177 (4), 14.8539 (9)
β (°) 90.943 (2)
V3)1410.73 (14)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.35 × 0.20 × 0.18
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.975, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
11401, 2856, 2261
Rint0.029
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.101, 1.03
No. of reflections2856
No. of parameters333
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.15

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

 

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana Inter­national, Karachi, Pakistan.

References

First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationEl-Seedi, H. R., Hazell, A. C. & Torssell, K. B. G. (1994). Phytochemistry, 35, 1297–1299.  CAS
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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