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

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ISSN: 2056-9890

(20S)-22-Acetoxymethyl-6β-meth­­oxy-3α,5-di­hydro-3′H-cyclo­propa[3α,5]-5α-pregnane

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 27 May 2009; accepted 31 May 2009; online 6 June 2009)

In the title steroid derivative, C25H40O3, the fused cyclo­propane unit that corresponds to a part of the A ring has a β-configuration and the associated cyclo­pentane ring an envelope-shaped conformation.

Related literature

For the synthesis and crystal structure of the iodo-substituted compound, see: Ketuly et al. (2009[Ketuly, K. A. A., Hadi, A. H. & Ng, S. W. (2009). Acta Cryst. E65, o1125.]). The absolute configuration of the acetoxymethyl title compound is that of the iodo-substituted compound.

[Scheme 1]

Experimental

Crystal data
  • C25H40O3

  • Mr = 388.57

  • Monoclinic, P 21

  • a = 9.8222 (1) Å

  • b = 7.6128 (1) Å

  • c = 15.2309 (2) Å

  • β = 107.604 (1)°

  • V = 1085.55 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.30 × 0.10 × 0.02 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 10411 measured reflections

  • 2674 independent reflections

  • 2550 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.092

  • S = 1.05

  • 2674 reflections

  • 258 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-211.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For the synthesis and crystal structure of the iodo-substituted steroid, see: Ketuly et al. (2009).

Experimental top

(20S)-22-Iodomethyl-6-methoxy-3,5-dihydro-3'H-cyclopropa[3α,5]-5-pregnane (Ketuly et al., 2009) (250 mg) was dissolved in pyridine (2 ml) and acetic anhydride (2 ml). The solution was heated at 353 K for an hour. The solvent was evaporated to give a product (280 mg), which was purified by recrystallization from ethanol (140 mg); m.p. 395–396 K. Mass spectrum: M+ 338. C&H elemental analysis: calc. C 77.27, H 10.38% (found: C 77.06, H 10.44%).

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C). 2271 Friedel pairs were merged.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C25H40O3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
(20S)-22-Acetoxymethyl-6β-methoxy-3α,5-dihydro-3'H-cyclopropa[3α,5]-5α-pregnane top
Crystal data top
C25H40O3F(000) = 428
Mr = 388.57Dx = 1.189 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 5999 reflections
a = 9.8222 (1) Åθ = 2.2–28.3°
b = 7.6128 (1) ŵ = 0.08 mm1
c = 15.2309 (2) ÅT = 100 K
β = 107.604 (1)°Plate, colorless
V = 1085.55 (2) Å30.30 × 0.10 × 0.02 mm
Z = 2
Data collection top
Bruker SMART APEX
diffractometer
2550 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
ω scansh = 1212
10411 measured reflectionsk = 99
2674 independent reflectionsl = 1919
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0668P)2 + 0.103P]
where P = (Fo2 + 2Fc2)/3
2674 reflections(Δ/σ)max = 0.001
258 parametersΔρmax = 0.30 e Å3
1 restraintΔρmin = 0.18 e Å3
Crystal data top
C25H40O3V = 1085.55 (2) Å3
Mr = 388.57Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.8222 (1) ŵ = 0.08 mm1
b = 7.6128 (1) ÅT = 100 K
c = 15.2309 (2) Å0.30 × 0.10 × 0.02 mm
β = 107.604 (1)°
Data collection top
Bruker SMART APEX
diffractometer
2550 reflections with I > 2σ(I)
10411 measured reflectionsRint = 0.023
2674 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0331 restraint
wR(F2) = 0.092H-atom parameters constrained
S = 1.05Δρmax = 0.30 e Å3
2674 reflectionsΔρmin = 0.18 e Å3
258 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.10395 (12)0.50018 (19)0.12290 (8)0.0237 (3)
O20.24166 (13)0.5963 (2)0.03933 (8)0.0286 (3)
O30.25451 (12)0.95997 (17)0.77203 (8)0.0214 (3)
C10.49210 (17)0.7214 (2)0.92678 (10)0.0213 (3)
H1C0.50640.83530.95970.026*
H1D0.46180.62390.95960.026*
C20.58913 (18)0.6782 (2)0.87028 (11)0.0206 (3)
H20.66540.76380.86830.025*
C30.6102 (2)0.4859 (3)0.85413 (12)0.0307 (4)
H3C0.67010.42880.91120.037*
H3D0.65610.47010.80500.037*
C40.4587 (2)0.4096 (2)0.82473 (12)0.0308 (4)
H4C0.43230.36960.87930.037*
H4D0.45240.30840.78290.037*
C50.35775 (17)0.5589 (2)0.77468 (10)0.0193 (3)
C60.2085 (2)0.5381 (3)0.78560 (12)0.0312 (4)
H6D0.21400.55440.85040.047*
H6E0.17190.42030.76550.047*
H6F0.14430.62630.74790.047*
C70.43341 (16)0.7250 (2)0.82255 (10)0.0158 (3)
C80.39518 (15)0.9004 (2)0.77576 (10)0.0153 (3)
H80.46690.98970.80920.018*
C90.23898 (18)0.9981 (3)0.86009 (12)0.0258 (4)
H9D0.14841.05960.85220.039*
H9E0.31831.07260.89490.039*
H9F0.23950.88820.89370.039*
C100.39576 (16)0.8908 (2)0.67622 (10)0.0158 (3)
H10C0.49510.87460.67490.019*
H10D0.36001.00320.64510.019*
C110.30351 (15)0.7405 (2)0.62360 (10)0.0133 (3)
H110.20210.76090.62170.016*
C120.35449 (16)0.5638 (2)0.67192 (10)0.0163 (3)
H120.45530.54750.67150.020*
C130.2681 (2)0.4112 (2)0.61596 (12)0.0254 (4)
H13C0.16740.42180.61550.030*
H13D0.30590.29900.64660.030*
C140.27319 (19)0.4064 (2)0.51608 (11)0.0221 (3)
H14C0.37250.38480.51590.027*
H14D0.21290.30870.48270.027*
C150.21989 (15)0.5799 (2)0.46676 (10)0.0149 (3)
C160.05902 (15)0.6053 (3)0.45320 (11)0.0224 (3)
H16D0.04260.61240.51350.034*
H16E0.00580.50560.41860.034*
H16F0.02640.71410.41890.034*
C170.31116 (15)0.7284 (2)0.52507 (10)0.0136 (3)
H170.41270.69960.53040.016*
C180.27348 (18)0.8908 (2)0.46325 (11)0.0190 (3)
H18E0.35260.97710.47910.023*
H18F0.18570.94790.46850.023*
C190.24985 (18)0.8151 (2)0.36523 (10)0.0212 (3)
H19C0.32680.85470.34030.025*
H19D0.15710.85520.32330.025*
C200.25155 (15)0.6111 (2)0.37410 (10)0.0155 (3)
H200.35160.57090.38230.019*
C210.15462 (16)0.5210 (2)0.28707 (10)0.0188 (3)
H210.05460.56330.27670.023*
C220.1550 (2)0.3196 (3)0.29402 (12)0.0285 (4)
H22A0.10660.26950.23330.043*
H22B0.10500.28380.33790.043*
H22C0.25380.27720.31530.043*
C230.20266 (16)0.5758 (2)0.20495 (10)0.0202 (3)
H23D0.20260.70540.19990.024*
H23E0.30070.53280.21260.024*
C240.13665 (17)0.5221 (2)0.04415 (11)0.0211 (3)
C250.0256 (2)0.4403 (4)0.03584 (12)0.0402 (5)
H25D0.00460.52560.08620.060*
H25E0.05700.40520.01650.060*
H25F0.06590.33670.05700.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0205 (5)0.0370 (7)0.0136 (5)0.0064 (5)0.0052 (4)0.0046 (5)
O20.0325 (6)0.0348 (7)0.0209 (6)0.0102 (6)0.0118 (5)0.0031 (6)
O30.0187 (5)0.0283 (6)0.0156 (5)0.0068 (5)0.0027 (4)0.0055 (5)
C10.0284 (8)0.0204 (8)0.0125 (7)0.0008 (7)0.0024 (6)0.0001 (6)
C20.0216 (8)0.0210 (8)0.0158 (7)0.0040 (6)0.0008 (6)0.0002 (6)
C30.0431 (11)0.0242 (9)0.0185 (8)0.0145 (8)0.0001 (7)0.0013 (7)
C40.0559 (12)0.0158 (8)0.0159 (8)0.0000 (9)0.0034 (7)0.0025 (7)
C50.0296 (8)0.0149 (7)0.0123 (7)0.0046 (7)0.0046 (5)0.0008 (6)
C60.0381 (10)0.0397 (11)0.0187 (8)0.0207 (9)0.0129 (7)0.0035 (8)
C70.0185 (7)0.0160 (7)0.0123 (7)0.0002 (6)0.0037 (5)0.0004 (6)
C80.0151 (6)0.0144 (7)0.0157 (7)0.0010 (6)0.0038 (5)0.0010 (6)
C90.0210 (7)0.0358 (10)0.0205 (8)0.0039 (7)0.0063 (6)0.0081 (7)
C100.0202 (7)0.0124 (7)0.0152 (7)0.0004 (6)0.0059 (5)0.0006 (6)
C110.0148 (6)0.0127 (7)0.0126 (6)0.0004 (5)0.0045 (5)0.0000 (5)
C120.0230 (7)0.0125 (7)0.0123 (7)0.0016 (6)0.0039 (5)0.0008 (6)
C130.0446 (10)0.0127 (7)0.0162 (8)0.0077 (7)0.0053 (7)0.0005 (6)
C140.0337 (9)0.0132 (7)0.0169 (8)0.0010 (7)0.0039 (6)0.0014 (6)
C150.0177 (7)0.0150 (7)0.0128 (6)0.0004 (6)0.0061 (5)0.0010 (6)
C160.0165 (7)0.0333 (9)0.0187 (7)0.0039 (7)0.0071 (5)0.0034 (7)
C170.0151 (6)0.0130 (6)0.0129 (7)0.0003 (6)0.0046 (5)0.0003 (6)
C180.0274 (8)0.0150 (7)0.0144 (7)0.0007 (6)0.0060 (6)0.0012 (6)
C190.0307 (8)0.0195 (8)0.0131 (7)0.0020 (7)0.0064 (6)0.0019 (6)
C200.0154 (6)0.0182 (7)0.0132 (7)0.0009 (6)0.0050 (5)0.0014 (6)
C210.0183 (7)0.0250 (8)0.0133 (7)0.0040 (6)0.0049 (6)0.0035 (6)
C220.0410 (10)0.0262 (9)0.0179 (8)0.0116 (8)0.0085 (7)0.0057 (7)
C230.0201 (7)0.0265 (8)0.0134 (7)0.0044 (7)0.0039 (5)0.0033 (6)
C240.0239 (7)0.0236 (8)0.0167 (7)0.0010 (6)0.0076 (6)0.0023 (6)
C250.0399 (10)0.0626 (15)0.0185 (9)0.0212 (11)0.0092 (7)0.0084 (9)
Geometric parameters (Å, º) top
O1—C241.3425 (19)C12—C131.536 (2)
O1—C231.4491 (18)C12—H121.0000
O2—C241.198 (2)C13—C141.538 (2)
O3—C91.4247 (19)C13—H13C0.9900
O3—C81.4388 (18)C13—H13D0.9900
C1—C21.501 (2)C14—C151.532 (2)
C1—C71.516 (2)C14—H14C0.9900
C1—H1C0.9900C14—H14D0.9900
C1—H1D0.9900C15—C161.5425 (19)
C2—C31.509 (2)C15—C171.545 (2)
C2—C71.524 (2)C15—C201.5525 (19)
C2—H21.0000C16—H16D0.9800
C3—C41.533 (3)C16—H16E0.9800
C3—H3C0.9900C16—H16F0.9800
C3—H3D0.9900C17—C181.530 (2)
C4—C51.549 (2)C17—H171.0000
C4—H4C0.9900C18—C191.551 (2)
C4—H4D0.9900C18—H18E0.9900
C5—C61.532 (2)C18—H18F0.9900
C5—C71.535 (2)C19—C201.559 (2)
C5—C121.5562 (19)C19—H19C0.9900
C6—H6D0.9800C19—H19D0.9900
C6—H6E0.9800C20—C211.540 (2)
C6—H6F0.9800C20—H201.0000
C7—C81.507 (2)C21—C231.523 (2)
C8—C101.520 (2)C21—C221.536 (3)
C8—H81.0000C21—H211.0000
C9—H9D0.9800C22—H22A0.9800
C9—H9E0.9800C22—H22B0.9800
C9—H9F0.9800C22—H22C0.9800
C10—C111.527 (2)C23—H23D0.9900
C10—H10C0.9900C23—H23E0.9900
C10—H10D0.9900C24—C251.503 (2)
C11—C171.5279 (19)C25—H25D0.9800
C11—C121.542 (2)C25—H25E0.9800
C11—H111.0000C25—H25F0.9800
C24—O1—C23116.28 (12)C12—C13—H13C109.0
C9—O3—C8113.69 (12)C14—C13—H13C109.0
C2—C1—C760.67 (10)C12—C13—H13D109.0
C2—C1—H1C117.7C14—C13—H13D109.0
C7—C1—H1C117.7H13C—C13—H13D107.8
C2—C1—H1D117.7C15—C14—C13110.86 (13)
C7—C1—H1D117.7C15—C14—H14C109.5
H1C—C1—H1D114.8C13—C14—H14C109.5
C1—C2—C3116.65 (16)C15—C14—H14D109.5
C1—C2—C760.16 (10)C13—C14—H14D109.5
C3—C2—C7108.47 (15)H14C—C14—H14D108.1
C1—C2—H2119.1C14—C15—C16110.98 (14)
C3—C2—H2119.1C14—C15—C17107.23 (12)
C7—C2—H2119.1C16—C15—C17112.21 (13)
C2—C3—C4104.22 (16)C14—C15—C20116.41 (13)
C2—C3—H3C110.9C16—C15—C20109.75 (12)
C4—C3—H3C110.9C17—C15—C2099.78 (11)
C2—C3—H3D110.9C15—C16—H16D109.5
C4—C3—H3D110.9C15—C16—H16E109.5
H3C—C3—H3D108.9H16D—C16—H16E109.5
C3—C4—C5106.63 (14)C15—C16—H16F109.5
C3—C4—H4C110.4H16D—C16—H16F109.5
C5—C4—H4C110.4H16E—C16—H16F109.5
C3—C4—H4D110.4C11—C17—C18118.76 (13)
C5—C4—H4D110.4C11—C17—C15114.60 (12)
H4C—C4—H4D108.6C18—C17—C15104.30 (11)
C6—C5—C7112.04 (14)C11—C17—H17106.1
C6—C5—C4111.19 (15)C18—C17—H17106.1
C7—C5—C4103.00 (12)C15—C17—H17106.1
C6—C5—C12112.47 (13)C17—C18—C19103.31 (13)
C7—C5—C12108.54 (12)C17—C18—H18E111.1
C4—C5—C12109.15 (14)C19—C18—H18E111.1
C5—C6—H6D109.5C17—C18—H18F111.1
C5—C6—H6E109.5C19—C18—H18F111.1
H6D—C6—H6E109.5H18E—C18—H18F109.1
C5—C6—H6F109.5C18—C19—C20106.99 (13)
H6D—C6—H6F109.5C18—C19—H19C110.3
H6E—C6—H6F109.5C20—C19—H19C110.3
C8—C7—C1118.20 (14)C18—C19—H19D110.3
C8—C7—C2120.24 (14)C20—C19—H19D110.3
C1—C7—C259.17 (10)H19C—C19—H19D108.6
C8—C7—C5119.34 (12)C21—C20—C15118.22 (12)
C1—C7—C5117.30 (14)C21—C20—C19112.44 (13)
C2—C7—C5107.80 (13)C15—C20—C19103.36 (12)
O3—C8—C7113.39 (13)C21—C20—H20107.4
O3—C8—C10105.61 (12)C15—C20—H20107.4
C7—C8—C10110.70 (13)C19—C20—H20107.4
O3—C8—H8109.0C23—C21—C22109.58 (14)
C7—C8—H8109.0C23—C21—C20108.70 (12)
C10—C8—H8109.0C22—C21—C20113.40 (14)
O3—C9—H9D109.5C23—C21—H21108.3
O3—C9—H9E109.5C22—C21—H21108.3
H9D—C9—H9E109.5C20—C21—H21108.3
O3—C9—H9F109.5C21—C22—H22A109.5
H9D—C9—H9F109.5C21—C22—H22B109.5
H9E—C9—H9F109.5H22A—C22—H22B109.5
C8—C10—C11112.28 (12)C21—C22—H22C109.5
C8—C10—H10C109.1H22A—C22—H22C109.5
C11—C10—H10C109.1H22B—C22—H22C109.5
C8—C10—H10D109.1O1—C23—C21107.87 (12)
C11—C10—H10D109.1O1—C23—H23D110.1
H10C—C10—H10D107.9C21—C23—H23D110.1
C10—C11—C17111.29 (12)O1—C23—H23E110.1
C10—C11—C12110.33 (11)C21—C23—H23E110.1
C17—C11—C12108.11 (12)H23D—C23—H23E108.4
C10—C11—H11109.0O2—C24—O1123.80 (15)
C17—C11—H11109.0O2—C24—C25124.99 (15)
C12—C11—H11109.0O1—C24—C25111.21 (14)
C13—C12—C11110.47 (12)C24—C25—H25D109.5
C13—C12—C5112.33 (13)C24—C25—H25E109.5
C11—C12—C5113.93 (13)H25D—C25—H25E109.5
C13—C12—H12106.5C24—C25—H25F109.5
C11—C12—H12106.5H25D—C25—H25F109.5
C5—C12—H12106.5H25E—C25—H25F109.5
C12—C13—C14112.90 (14)
C7—C1—C2—C396.93 (17)C4—C5—C12—C1373.88 (17)
C1—C2—C3—C447.2 (2)C6—C5—C12—C1176.57 (17)
C7—C2—C3—C418.01 (19)C7—C5—C12—C1147.97 (17)
C2—C3—C4—C530.41 (18)C4—C5—C12—C11159.54 (13)
C3—C4—C5—C6150.84 (15)C11—C12—C13—C1455.86 (19)
C3—C4—C5—C730.67 (17)C5—C12—C13—C14175.72 (14)
C3—C4—C5—C1284.52 (16)C12—C13—C14—C1556.96 (19)
C2—C1—C7—C8110.21 (16)C13—C14—C15—C1667.31 (17)
C2—C1—C7—C595.32 (16)C13—C14—C15—C1755.57 (16)
C1—C2—C7—C8106.81 (16)C13—C14—C15—C20166.22 (13)
C3—C2—C7—C8142.48 (15)C10—C11—C17—C1855.54 (16)
C3—C2—C7—C1110.71 (16)C12—C11—C17—C18176.85 (13)
C1—C2—C7—C5111.68 (14)C10—C11—C17—C15179.67 (12)
C3—C2—C7—C50.96 (18)C12—C11—C17—C1559.02 (15)
C6—C5—C7—C879.26 (17)C14—C15—C17—C1159.41 (16)
C4—C5—C7—C8161.16 (15)C16—C15—C17—C1162.70 (17)
C12—C5—C7—C845.53 (18)C20—C15—C17—C11178.85 (12)
C6—C5—C7—C174.92 (18)C14—C15—C17—C18169.08 (12)
C4—C5—C7—C144.66 (17)C16—C15—C17—C1868.81 (15)
C12—C5—C7—C1160.29 (13)C20—C15—C17—C1847.34 (14)
C6—C5—C7—C2138.82 (14)C11—C17—C18—C19163.91 (12)
C4—C5—C7—C219.24 (16)C15—C17—C18—C1934.87 (15)
C12—C5—C7—C296.40 (14)C17—C18—C19—C208.70 (17)
C9—O3—C8—C765.98 (17)C14—C15—C20—C2179.65 (17)
C9—O3—C8—C10172.64 (14)C16—C15—C20—C2147.44 (19)
C1—C7—C8—O384.03 (16)C17—C15—C20—C21165.44 (13)
C2—C7—C8—O3152.90 (13)C14—C15—C20—C19155.41 (14)
C5—C7—C8—O369.91 (17)C16—C15—C20—C1977.50 (16)
C1—C7—C8—C10157.49 (13)C17—C15—C20—C1940.50 (14)
C2—C7—C8—C1088.62 (16)C18—C19—C20—C21148.82 (13)
C5—C7—C8—C1048.57 (18)C18—C19—C20—C1520.22 (16)
O3—C8—C10—C1170.54 (16)C15—C20—C21—C23177.98 (14)
C7—C8—C10—C1152.56 (16)C19—C20—C21—C2357.63 (17)
C8—C10—C11—C17177.44 (12)C15—C20—C21—C2259.89 (19)
C8—C10—C11—C1257.44 (16)C19—C20—C21—C22179.76 (15)
C10—C11—C12—C13176.47 (13)C24—O1—C23—C21174.41 (14)
C17—C11—C12—C1354.57 (16)C22—C21—C23—O159.70 (18)
C10—C11—C12—C555.99 (16)C20—C21—C23—O1175.88 (13)
C17—C11—C12—C5177.89 (12)C23—O1—C24—O21.3 (3)
C6—C5—C12—C1350.0 (2)C23—O1—C24—C25179.22 (17)
C7—C5—C12—C13174.54 (13)

Experimental details

Crystal data
Chemical formulaC25H40O3
Mr388.57
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)9.8222 (1), 7.6128 (1), 15.2309 (2)
β (°) 107.604 (1)
V3)1085.55 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.10 × 0.02
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10411, 2674, 2550
Rint0.023
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.092, 1.05
No. of reflections2674
No. of parameters258
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.18

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

We thank the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–211.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKetuly, K. A. A., Hadi, A. H. & Ng, S. W. (2009). Acta Cryst. E65, o1125.  Web of Science CSD CrossRef IUCr Journals 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. (2009). publCIF. In preparation.  Google Scholar

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