PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2174.
Published online 2009 August 19. doi:  10.1107/S1600536809031547
PMCID: PMC2970092

5-Bromo-2,3-dihydro-1H-cyclo­penta­[a]naphthalen-1-one

Abstract

The title compound, C13H9BrO, has been synthesized by the intra­molecular Friedel–Crafts reaction of 1-(1-bromo-4-naphth­yl)-3-chloro­propan-1-one. There are two approximately planar [maximum deviations of 0.8 (2) and 0.4 (2) Å in the two mol­ecules] molecules in the asymmetric unit. The dihedral angle between their mean planes is 19.72 (8)°. Weak inter­molecular C—H(...)O hydrogen bonding is present in the crystal structure.

Related literature

The trimer of the title compound is a potential inter­mediate in the synthesis of fullerenes, see: Boorum et al. (2001 [triangle]); Scott et al. (1996 [triangle]). The Aldol cyclo­trimerization of the title compound is widely used in the synthesis of fullerenes and bowl-shaped compounds, see: Amick & Scott (2007 [triangle]). For a related structure, see: Sil et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2174-scheme1.jpg

Experimental

Crystal data

  • C13H9BrO
  • M r = 261.10
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2174-efi1.jpg
  • a = 7.369 (2) Å
  • b = 9.986 (3) Å
  • c = 14.177 (5) Å
  • α = 87.763 (6)°
  • β = 78.991 (6)°
  • γ = 87.154 (7)°
  • V = 1022.3 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.99 mm−1
  • T = 298 K
  • 0.09 × 0.08 × 0.06 mm

Data collection

  • Oxford Gemini S Ultra diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 [triangle]) T min = 0.716, T max = 0.796
  • 5159 measured reflections
  • 3524 independent reflections
  • 2663 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.119
  • S = 0.97
  • 3524 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.52 e Å−3
  • Δρmin = −0.40 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031547/xu2577sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031547/xu2577Isup2.hkl

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

Acknowledgments

This work was supported by the NFFTBS (No. J0630429).

supplementary crystallographic information

Comment

The title compound is the medial compound for the synthesis of its trimmer molecule. In the acid conditions, the trimmer molecule can be obtained by the Aldol cyclotrimerization of 5-bromo-2,3-dihydrocyclopenta[a]naphthalen-1-one. These kinds of the trimmers are the potential intermediate in the synthesis of fullerenes (Boorum et al., 2001; Scott et al., 1996). So this method was widely used in the organic synthesis of fullerenes and bowl-shaped compounds (Amick & Scott, 2007).

The molecular structure is depicted in Fig. 1. Bond lengths and angles are in good agreement with previous reported for similar compounds (Sil et al., 2004). The molecule assumes a co-planar structure, except methylene H atoms. The asymmetric unit of the crystal structure contains two independent molecules, the two molecular planes make a dihedral angle of 19.72 (8)° with respect to each other. Weak intermolecular C—H···O hydrogen bonding (Table 1) is present in the crystal structure(Fig. 2).

Experimental

All reagents and solvents were used as obtained commercially without further purification. The title compound was synthesized by adding 1-(1-bromonaphthalen-4-yl)-3-chloropropan-1-one (1.4 mL) to concentrated H2SO4 (11 ml) at room temperature. The resulting mixture was stirred at 383 K for 3 h, after cooling to room temperature, the mixture was poured into water-ice slowly. The aqueous layer was extracted with cyclohexane (3 × 60 mL). The organic layers were combined and washed with saturated NaHCO3 solution (120 mL), saturated brine (3 × 60 ml), and dried over MgSO4, and concentrated under reduced pressure to provide the title compound. The compound was dissolved in CH2Cl2 and kept in darkness for several days, yellow block-shaped single crystals were obtained.

Refinement

H atoms were generated geometrically with C—H 0.93 or 0.97 Å and were allowed to ride on their parent atoms in the riding model approximations, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound with 30% probability displacement ellipsoids.

Crystal data

C13H9BrOZ = 4
Mr = 261.10F(000) = 520
Triclinic, P1Dx = 1.696 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.369 (2) ÅCell parameters from 2244 reflections
b = 9.986 (3) Åθ = 5.0–51.6°
c = 14.177 (5) ŵ = 3.99 mm1
α = 87.763 (6)°T = 298 K
β = 78.991 (6)°Block, yellow
γ = 87.154 (7)°0.09 × 0.08 × 0.06 mm
V = 1022.3 (5) Å3

Data collection

Oxford Gemini S Ultra diffractometer3524 independent reflections
Radiation source: fine-focus sealed tube2663 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 16.1903 pixels mm-1θmax = 25.0°, θmin = 2.0°
ω scansh = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)k = −11→7
Tmin = 0.716, Tmax = 0.796l = −16→16
5159 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.0728P)2] where P = (Fo2 + 2Fc2)/3
3524 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = −0.40 e Å3

Special details

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)

xyzUiso*/Ueq
Br10.65084 (6)0.55540 (4)0.27810 (3)0.06465 (19)
Br20.91872 (7)0.04342 (5)0.24015 (3)0.07118 (19)
C10.8141 (5)0.4593 (4)−0.1539 (3)0.0496 (9)
C20.8305 (6)0.3098 (4)−0.1488 (3)0.0595 (11)
H2A0.95220.2786−0.18150.071*
H2B0.73840.2722−0.17940.071*
C30.8005 (6)0.2664 (4)−0.0430 (3)0.0574 (10)
H3A0.69530.2096−0.02620.069*
H3B0.90930.2181−0.02790.069*
C40.7646 (5)0.3963 (3)0.0089 (3)0.0428 (8)
C50.7302 (5)0.4116 (4)0.1088 (3)0.0507 (9)
H5A0.72910.33730.15050.061*
C60.6988 (5)0.5365 (4)0.1428 (3)0.0454 (9)
C70.7025 (5)0.6556 (3)0.0827 (2)0.0406 (8)
C80.6704 (5)0.7859 (3)0.1171 (3)0.0480 (9)
H8A0.64510.79850.18300.058*
C90.6756 (5)0.8937 (4)0.0558 (3)0.0540 (10)
H9A0.65440.97940.08010.065*
C100.7121 (5)0.8774 (4)−0.0427 (3)0.0527 (9)
H10A0.71460.9523−0.08400.063*
C110.7444 (5)0.7531 (3)−0.0796 (3)0.0477 (9)
H11A0.77010.7435−0.14590.057*
C120.7392 (5)0.6376 (3)−0.0175 (2)0.0397 (8)
C130.7711 (5)0.5055 (4)−0.0526 (3)0.0416 (8)
C140.6249 (5)−0.0807 (4)0.6648 (3)0.0528 (10)
C150.5904 (6)−0.2280 (4)0.6573 (3)0.0656 (12)
H15A0.6664−0.28290.69380.079*
H15B0.4615−0.24520.68250.079*
C160.6392 (5)−0.2604 (4)0.5528 (3)0.0551 (10)
H16A0.5316−0.28780.52960.066*
H16B0.7347−0.33160.54200.066*
C170.7091 (4)−0.1300 (3)0.5032 (3)0.0435 (9)
C180.7752 (5)−0.1078 (4)0.4049 (3)0.0498 (9)
H18A0.7815−0.17670.36200.060*
C190.8295 (5)0.0155 (4)0.3739 (3)0.0462 (9)
C200.8236 (4)0.1243 (3)0.4364 (3)0.0416 (8)
C210.8801 (5)0.2544 (4)0.4031 (3)0.0491 (9)
H21A0.92470.27180.33810.059*
C220.8680 (5)0.3541 (4)0.4681 (3)0.0569 (11)
H22A0.90330.43960.44590.068*
C230.8054 (5)0.3321 (4)0.5651 (3)0.0543 (10)
H23A0.80140.40110.60770.065*
C240.7489 (5)0.2069 (4)0.5980 (3)0.0542 (10)
H24A0.70430.19230.66330.065*
C250.7569 (5)0.1006 (3)0.5352 (3)0.0429 (9)
C260.7001 (5)−0.0297 (3)0.5667 (3)0.0414 (8)
O10.8324 (5)0.5286 (3)−0.2259 (2)0.0722 (9)
O20.5922 (4)−0.0199 (3)0.7378 (2)0.0781 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0910 (4)0.0609 (3)0.0390 (3)−0.0119 (2)−0.0041 (2)0.00645 (18)
Br20.0765 (3)0.0813 (4)0.0490 (3)−0.0153 (2)0.0092 (2)−0.0078 (2)
C10.045 (2)0.051 (2)0.054 (2)0.0024 (17)−0.0130 (19)−0.0079 (19)
C20.065 (3)0.057 (3)0.056 (3)−0.003 (2)−0.008 (2)−0.015 (2)
C30.058 (3)0.041 (2)0.074 (3)−0.0061 (18)−0.011 (2)−0.0051 (19)
C40.0401 (19)0.037 (2)0.051 (2)−0.0083 (15)−0.0050 (16)−0.0017 (16)
C50.059 (2)0.042 (2)0.050 (2)−0.0074 (18)−0.0108 (19)0.0109 (17)
C60.050 (2)0.047 (2)0.039 (2)−0.0091 (17)−0.0047 (17)0.0022 (16)
C70.0395 (19)0.041 (2)0.041 (2)−0.0082 (15)−0.0069 (16)0.0048 (15)
C80.053 (2)0.045 (2)0.045 (2)−0.0002 (17)−0.0088 (18)−0.0033 (17)
C90.064 (3)0.035 (2)0.063 (3)−0.0005 (18)−0.013 (2)−0.0006 (17)
C100.062 (3)0.043 (2)0.051 (2)−0.0005 (18)−0.0076 (19)0.0106 (17)
C110.058 (2)0.045 (2)0.039 (2)−0.0037 (18)−0.0066 (18)0.0081 (16)
C120.0379 (19)0.0370 (19)0.044 (2)−0.0035 (15)−0.0072 (16)0.0030 (15)
C130.039 (2)0.042 (2)0.044 (2)−0.0062 (15)−0.0080 (16)−0.0005 (15)
C140.045 (2)0.061 (3)0.054 (3)−0.0040 (19)−0.0141 (19)0.012 (2)
C150.059 (3)0.061 (3)0.080 (3)−0.013 (2)−0.024 (2)0.031 (2)
C160.046 (2)0.038 (2)0.083 (3)−0.0077 (17)−0.017 (2)0.0108 (19)
C170.0309 (18)0.042 (2)0.059 (2)−0.0021 (15)−0.0142 (17)0.0055 (17)
C180.045 (2)0.041 (2)0.064 (3)−0.0022 (17)−0.0090 (19)−0.0090 (18)
C190.040 (2)0.055 (2)0.040 (2)−0.0015 (17)−0.0010 (16)0.0007 (16)
C200.0318 (18)0.041 (2)0.051 (2)−0.0002 (15)−0.0073 (16)0.0004 (16)
C210.043 (2)0.048 (2)0.058 (2)−0.0121 (17)−0.0121 (18)0.0083 (18)
C220.059 (3)0.034 (2)0.081 (3)−0.0123 (18)−0.020 (2)0.004 (2)
C230.053 (2)0.045 (2)0.067 (3)−0.0079 (18)−0.015 (2)−0.016 (2)
C240.056 (2)0.057 (3)0.052 (2)−0.0019 (19)−0.013 (2)−0.0053 (19)
C250.0360 (19)0.042 (2)0.052 (2)0.0007 (15)−0.0123 (17)−0.0037 (16)
C260.040 (2)0.042 (2)0.044 (2)−0.0029 (16)−0.0117 (16)0.0053 (15)
O10.098 (2)0.079 (2)0.0383 (17)0.0139 (17)−0.0135 (16)−0.0042 (15)
O20.092 (2)0.089 (2)0.052 (2)−0.0133 (18)−0.0097 (17)0.0082 (17)

Geometric parameters (Å, °)

Br1—C61.898 (4)C12—C131.421 (5)
Br2—C191.899 (4)C14—O21.198 (5)
C1—O11.200 (5)C14—C261.476 (5)
C1—C21.492 (5)C14—C151.517 (6)
C1—C131.496 (5)C15—C161.501 (6)
C2—C31.522 (6)C15—H15A0.9700
C2—H2A0.9700C15—H15B0.9700
C2—H2B0.9700C16—C171.521 (5)
C3—C41.504 (5)C16—H16A0.9700
C3—H3A0.9700C16—H16B0.9700
C3—H3B0.9700C17—C261.364 (5)
C4—C131.366 (5)C17—C181.398 (5)
C4—C51.403 (5)C18—C191.345 (5)
C5—C61.349 (5)C18—H18A0.9300
C5—H5A0.9300C19—C201.423 (5)
C6—C71.434 (5)C20—C251.408 (5)
C7—C81.400 (5)C20—C211.420 (5)
C7—C121.412 (5)C21—C221.371 (5)
C8—C91.354 (5)C21—H21A0.9300
C8—H8A0.9300C22—C231.376 (6)
C9—C101.386 (5)C22—H22A0.9300
C9—H9A0.9300C23—C241.373 (6)
C10—C111.358 (5)C23—H23A0.9300
C10—H10A0.9300C24—C251.404 (5)
C11—C121.421 (5)C24—H24A0.9300
C11—H11A0.9300C25—C261.416 (5)
O1—C1—C2126.2 (4)O2—C14—C26128.1 (4)
O1—C1—C13126.9 (4)O2—C14—C15124.9 (4)
C2—C1—C13106.9 (3)C26—C14—C15107.0 (3)
C1—C2—C3107.6 (3)C16—C15—C14107.2 (3)
C1—C2—H2A110.2C16—C15—H15A110.3
C3—C2—H2A110.2C14—C15—H15A110.3
C1—C2—H2B110.2C16—C15—H15B110.3
C3—C2—H2B110.2C14—C15—H15B110.3
H2A—C2—H2B108.5H15A—C15—H15B108.5
C4—C3—C2103.8 (3)C15—C16—C17104.2 (3)
C4—C3—H3A111.0C15—C16—H16A110.9
C2—C3—H3A111.0C17—C16—H16A110.9
C4—C3—H3B111.0C15—C16—H16B110.9
C2—C3—H3B111.0C17—C16—H16B110.9
H3A—C3—H3B109.0H16A—C16—H16B108.9
C13—C4—C5120.9 (3)C26—C17—C18121.2 (3)
C13—C4—C3112.5 (3)C26—C17—C16111.9 (4)
C5—C4—C3126.6 (3)C18—C17—C16127.0 (3)
C6—C5—C4118.4 (3)C19—C18—C17118.5 (3)
C6—C5—H5A120.8C19—C18—H18A120.7
C4—C5—H5A120.8C17—C18—H18A120.7
C5—C6—C7123.8 (3)C18—C19—C20123.1 (4)
C5—C6—Br1117.9 (3)C18—C19—Br2117.8 (3)
C7—C6—Br1118.3 (3)C20—C19—Br2119.1 (3)
C8—C7—C12119.0 (3)C25—C20—C21119.4 (3)
C8—C7—C6124.4 (3)C25—C20—C19117.9 (3)
C12—C7—C6116.7 (3)C21—C20—C19122.8 (4)
C9—C8—C7121.0 (4)C22—C21—C20119.0 (4)
C9—C8—H8A119.5C22—C21—H21A120.5
C7—C8—H8A119.5C20—C21—H21A120.5
C8—C9—C10120.6 (4)C21—C22—C23122.3 (4)
C8—C9—H9A119.7C21—C22—H22A118.8
C10—C9—H9A119.7C23—C22—H22A118.8
C11—C10—C9120.6 (4)C24—C23—C22119.1 (4)
C11—C10—H10A119.7C24—C23—H23A120.4
C9—C10—H10A119.7C22—C23—H23A120.4
C10—C11—C12120.4 (3)C23—C24—C25121.4 (4)
C10—C11—H11A119.8C23—C24—H24A119.3
C12—C11—H11A119.8C25—C24—H24A119.3
C7—C12—C13119.1 (3)C24—C25—C20118.7 (4)
C7—C12—C11118.4 (3)C24—C25—C26122.9 (4)
C13—C12—C11122.5 (3)C20—C25—C26118.3 (3)
C4—C13—C12121.1 (3)C17—C26—C25121.0 (3)
C4—C13—C1109.1 (3)C17—C26—C14109.7 (3)
C12—C13—C1129.7 (3)C25—C26—C14129.3 (3)
O1—C1—C2—C3178.9 (4)O1—C1—C2—C3178.9 (4)
C13—C1—C2—C3−1.1 (4)C13—C1—C2—C3−1.1 (4)
C1—C2—C3—C40.8 (4)C1—C2—C3—C40.8 (4)
C2—C3—C4—C13−0.2 (4)C2—C3—C4—C13−0.2 (4)
C2—C3—C4—C5−179.3 (4)C2—C3—C4—C5−179.3 (4)
C13—C4—C5—C61.7 (5)C13—C4—C5—C61.7 (5)
C3—C4—C5—C6−179.3 (3)C3—C4—C5—C6−179.3 (3)
C4—C5—C6—C7−1.4 (6)C4—C5—C6—C7−1.4 (6)
C4—C5—C6—Br1179.6 (3)C4—C5—C6—Br1179.6 (3)
C5—C6—C7—C8−179.9 (3)C5—C6—C7—C8−179.9 (3)
Br1—C6—C7—C8−0.9 (5)Br1—C6—C7—C8−0.9 (5)
C5—C6—C7—C120.8 (5)C5—C6—C7—C120.8 (5)
Br1—C6—C7—C12179.8 (2)Br1—C6—C7—C12179.8 (2)
C12—C7—C8—C9−0.5 (5)C12—C7—C8—C9−0.5 (5)
C6—C7—C8—C9−179.8 (4)C6—C7—C8—C9−179.8 (4)
C7—C8—C9—C100.3 (6)C7—C8—C9—C100.3 (6)
C8—C9—C10—C11−0.4 (6)C8—C9—C10—C11−0.4 (6)
C9—C10—C11—C120.7 (6)C9—C10—C11—C120.7 (6)
C8—C7—C12—C13−179.7 (3)C8—C7—C12—C13−179.7 (3)
C6—C7—C12—C13−0.5 (5)C6—C7—C12—C13−0.5 (5)
C8—C7—C12—C110.8 (5)C8—C7—C12—C110.8 (5)
C6—C7—C12—C11−179.9 (3)C6—C7—C12—C11−179.9 (3)
C10—C11—C12—C7−0.9 (5)C10—C11—C12—C7−0.9 (5)
C10—C11—C12—C13179.7 (3)C10—C11—C12—C13179.7 (3)
C5—C4—C13—C12−1.4 (5)C5—C4—C13—C12−1.4 (5)
C3—C4—C13—C12179.4 (3)C3—C4—C13—C12179.4 (3)
C5—C4—C13—C1178.7 (3)C5—C4—C13—C1178.7 (3)
C3—C4—C13—C1−0.5 (4)C3—C4—C13—C1−0.5 (4)
C7—C12—C13—C40.8 (5)C7—C12—C13—C40.8 (5)
C11—C12—C13—C4−179.8 (3)C11—C12—C13—C4−179.8 (3)
C7—C12—C13—C1−179.3 (3)C7—C12—C13—C1−179.3 (3)
C11—C12—C13—C10.0 (6)C11—C12—C13—C10.0 (6)
O1—C1—C13—C4−179.0 (4)O1—C1—C13—C4−179.0 (4)
C2—C1—C13—C41.0 (4)C2—C1—C13—C41.0 (4)
O1—C1—C13—C121.1 (7)O1—C1—C13—C121.1 (7)
C2—C1—C13—C12−178.9 (3)C2—C1—C13—C12−178.9 (3)
O2—C14—C15—C16176.4 (4)O2—C14—C15—C16176.4 (4)
C26—C14—C15—C16−2.3 (4)C26—C14—C15—C16−2.3 (4)
C14—C15—C16—C172.3 (4)C14—C15—C16—C172.3 (4)
C15—C16—C17—C26−1.6 (4)C15—C16—C17—C26−1.6 (4)
C15—C16—C17—C18178.8 (3)C15—C16—C17—C18178.8 (3)
C26—C17—C18—C19−0.3 (5)C26—C17—C18—C19−0.3 (5)
C16—C17—C18—C19179.3 (3)C16—C17—C18—C19179.3 (3)
C17—C18—C19—C200.3 (5)C17—C18—C19—C200.3 (5)
C17—C18—C19—Br2−180.0 (2)C17—C18—C19—Br2−180.0 (2)
C18—C19—C20—C25−0.2 (5)C18—C19—C20—C25−0.2 (5)
Br2—C19—C20—C25−180.0 (2)Br2—C19—C20—C25−180.0 (2)
C18—C19—C20—C21−179.6 (3)C18—C19—C20—C21−179.6 (3)
Br2—C19—C20—C210.6 (4)Br2—C19—C20—C210.6 (4)
C25—C20—C21—C22−0.1 (5)C25—C20—C21—C22−0.1 (5)
C19—C20—C21—C22179.3 (3)C19—C20—C21—C22179.3 (3)
C20—C21—C22—C231.0 (5)C20—C21—C22—C231.0 (5)
C21—C22—C23—C24−1.5 (6)C21—C22—C23—C24−1.5 (6)
C22—C23—C24—C251.2 (6)C22—C23—C24—C251.2 (6)
C23—C24—C25—C20−0.4 (5)C23—C24—C25—C20−0.4 (5)
C23—C24—C25—C26179.9 (3)C23—C24—C25—C26179.9 (3)
C21—C20—C25—C24−0.2 (5)C21—C20—C25—C24−0.2 (5)
C19—C20—C25—C24−179.6 (3)C19—C20—C25—C24−179.6 (3)
C21—C20—C25—C26179.5 (3)C21—C20—C25—C26179.5 (3)
C19—C20—C25—C260.1 (5)C19—C20—C25—C260.1 (5)
C18—C17—C26—C250.2 (5)C18—C17—C26—C250.2 (5)
C16—C17—C26—C25−179.4 (3)C16—C17—C26—C25−179.4 (3)
C18—C17—C26—C14179.8 (3)C18—C17—C26—C14179.8 (3)
C16—C17—C26—C140.2 (4)C16—C17—C26—C140.2 (4)
C24—C25—C26—C17179.6 (3)C24—C25—C26—C17179.6 (3)
C20—C25—C26—C17−0.1 (5)C20—C25—C26—C17−0.1 (5)
C24—C25—C26—C140.0 (6)C24—C25—C26—C140.0 (6)
C20—C25—C26—C14−179.7 (3)C20—C25—C26—C14−179.7 (3)
O2—C14—C26—C17−177.3 (4)O2—C14—C26—C17−177.3 (4)
C15—C14—C26—C171.3 (4)C15—C14—C26—C171.3 (4)
O2—C14—C26—C252.2 (6)O2—C14—C26—C252.2 (6)
C15—C14—C26—C25−179.1 (3)C15—C14—C26—C25−179.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C15—H15A···O1i0.972.543.495 (5)167

Symmetry codes: (i) x, y−1, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2577).

References

  • Amick, A. W. & Scott, L. T. (2007). J. Org. Chem.72, 3412–3418. [PubMed]
  • Boorum, M. M., Vasil’ev, Y. V., Drewello, T. & Scott, L. T. (2001). Science, 294, 828–831. [PubMed]
  • Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, England.
  • Scott, L. T., Bratcher, M. S. & Hagen, S. (1996). J. Am. Chem. Soc.118, 8743–8744.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sil, D., Sharon, A., Maulik, P. R. & Ram, V. J. (2004). Tetrahedron Lett.45, 6619–6621.
  • Westrip, S. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography