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Nootkatone, or (4R,4aS,6R)-4,4a,5,6,7,8-hexa­hydro-4,4a-di­methyl-6-(1-methyl­ethenyl)­naphthalen-2(3H)-one, C15H22O, a sesquiterpene with strong repellent properties against Formosan subterranean termites and other insects, has the valencene skeleton. The di­bromo derivative (1S,3R,4S,4aS,6R,8aR)-1,3-di­bromo-6-iso­propyl-4,4a-di­methyl-1,2,3,4,5,6,7,8-octa­hydro­naphthalen-2-one, C15H24Br2O, has two independent mol­ecules in the asymmetric unit, which differ in the rotation of the iso­propyl group with respect to the main skeleton. The C-Br distances are in the range 1.950 (4)-1.960 (4) Å. Both independent molecules form zigzag chains, with very short intermolecular carbonyl-carbonyl interactions, having the perpendicular motif and O...C distances of 2.886 (6) and 2.898 (6) Å. These chains are flanked by intermolecular Br...Br interactions of distances in the range 4.067 (1)-4.218 (1) Å. The absolute configuration of the di­bromo derivative was determined, from which that of nootkatone was inferred.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010300684X/sq1013sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010300684X/sq1013Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010300684X/sq1013IIsup3.hkl
Contains datablock II

CCDC references: 214169; 214170

Comment top

Nootkatone, (I), the major flavorant of grapefruit, is a valencene-class sesquiterpene ketone, which was first isolated from Alaskan yellow cedar (Erdtman & Hirose, 1962), and is a minor component of some vetiver oils. Part of the interest in this class of compounds is their termiticidic and insect repellent activity, particularly towards the Formosan subterranean termite (Zhu, Henderson, Chen, Fei & Laine, 2001; Zhu, Henderson, Chen, Fei, Maistrello & Laine, 2001). Nootkatone appears to be non-toxic to humans, as it is currently added to juices to impart a grapefruit essence. We have been studying nootkatone because of its potent and seemingly receptor-specific activity, and its potential commercial importance as a termiticide. Since absolute structure is usually an important factor controlling biological activity, we have determined the crystal structure of this low-melting (m.p. 309–311 K) natural product and sought to definitively establish its absolute structure. We are not aware of any previous absolute structure determinations by X-ray methods of valencene-class sesquiterpenoids or those of the eremophilene class, differing from the valencenes by the configuration at C4 and C5. To this end, we attempted to synthesize a bromo derivative of nootkatone, but were unsuccessful in growing suitable crystals of any such compounds. We thus turned to bromination of tetrahydronootkatone, which has the same absolute configuration, because a published synthesis of 3-α-bromo-tetrahydronootkatone (m.p. 353–351 K) was available (MacLeod, 1965). In our hands, the MacLeod synthesis did not yield the expected product, but instead yielded compound (II) (m.p. 406–408 K; Sauer et al., 2003), a dibromo derivative. Fortunately, it crystallized well and was sufficient for absolute configuration determination. We report here the low-temperature structures of both nootkatone, (I), and the dibromo derivative (II).

The structure of (I) is shown in Fig. 1, which illustrates its valencene-type skeleton, with methyl groups C14 and C15 α-oriented, and the substituent at C7 β-oriented. The C5–C10 ring is in a slightly flattened chair conformation, with endocyclic torsion angles in the range 45.3 (2)–57.5 (2)°, the flattening being a result of the C1C10 double bond. The presence of the C1C10 unsaturation in the other ring and the ketone conjugated to it causes it to have a conformation in which all atoms but C4 are nearly coplanar. Atom C4 lies 0.624 (2) Å out of the best plane of the other five, which exhibit a maximum deviation of 0.074 (2) Å for C2. The packing for (I) is unremarkable; in particular, molecules do not form carbonyl–carbonyl intermolcular interactions of the type described by Allen et al. (1998). The absolute configuration of (I) is inferred to be that shown in Fig. 1, corresponding to the configuration directly determined for (II). The skeleton of nootkatone is shared with tetrahydronootkatone, vetivone and valencene, all of which have the same configuration. All have strong repellent properties against the Formosan subterranean termite except for valencene, which lacks the C2-ketone group and is relatively inactive. Thus, we conclude that the binding site must recognize the stereochemistry of the skeleton, but require the ketone.

The absolute structure of (II) is shown in Fig. 2, which illustrates one of the two independent molecules. There are no significant differences between corresponding bond distances in the two molecules, nor between their endocyclic torsion angles. Both rings in the molecule have chair conformations; that carrying the ketone being slightly flattened, with endocyclic torsion angles in the range 40.5 (5)–64.5 (5)°, while the other ring is much less flattened compared to that of (I), having torsion angles in the range 52.6 (5)–60.0 (5)°. The main difference between molecules A and B is in the rotation of the isopropyl group with respect to the main skeleton. The difference in rotation is 125.2 (8)°, such that C13 is anti to C6 in the molecule A and anti to C8 in the molecule B.

The most remarkable feature of the structure of (II) is its packing. Both molecules form zigzag chains of carbonyl–carbonyl intermolecular interactions in the [010] direction, propagated by 21 axes. The geometry of the interactions is the perpendicular motif, reported by Allen et al. (1998) to occur in about 1.3% of the carbonyl-containing structures in the Cambridge Structural Database (Allen & Kennard, 1993). The CO···C angles here are nearly linear, with C2AO1A···C2Ai = 176.4 (4)° and C2BO1B···C2Bii = 175.8 (4)° [symmetry codes: (i) 1 − x, 1/2 + y, 1 − z; (ii) −x, 1/2 + y, −z]. The C···O distances are much shorter than expected [2.886 (6) Å for the the A chain and 2.898 (6) Å for the B chain], representing some of the shortest such interactions known. Allen et al. (1998) reported that only 26% of such interactions are shorter than the sum of C and O van der Waals radii (3.22 Å), with a median of 3.35 Å. The shortness of these contacts may be related to the fact that the ketone substituent is flanked by two C—Br bonds, both of which are equatorial on the six-membered ring. Thus, each carbonyl–carbonyl interaction is accompanied by two intermolecular Br···Br interactions. These distances are 4.067 (1) and 4.218 (1) Å for the A chain, and 4.147 (1) and 4.172 (1) Å for the B chain, slightly longer than 3.70 Å, which is twice the van der Waals radius of Br (Bondi, 1964).

Experimental top

A sample of (+)-nootkatone, [α]D = +166°, was purchased from Aromor Inc., Israel. A suitable single-crystal was chosen without recrystallization. To a solution of tetrahydronootkatone (0.5 g, 2.25 mmol), also obtained from Aromor, in glacial acetic acid (11 ml) was added 1 equivalent of a 1 M solution of Br2 in acetic acid. The solution was stirred at room temperature for 1 h under a positive N2 pressure. The reaction mixture was then poured over water and extracted with CHCl3. The organic layers were combined, dried over Na2SO4, filtered, and concentrated to give a thick oil. The dibromo derivative [(II), m.p. 406–408 K, [α]D = +0.28°] was crystallized from hexanes (0.531 g, 32.6% yield).

Refinement top

H atoms were treated as riding in idealized positions, with C—H distances in the range 0.95–1.00 Å, depending on the atom type. A torsional parameter was refined for each methyl group. Displacement parameters for H atoms were assigned as Uiso = 1.2Ueq of the attached atom (1.5 for methyl groups). Friedel pairs were averaged for (I). For the dibromo derivative, (II), the absolute configuration was determined by refinement of the Flack (1983) parameter, using 4216 Friedel pairs. All residual peaks greater than 0.69 e Å−3 were within 1.1 Å of bromine positions.

Computing details top

For both compounds, data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEP-3 (Farrugia, 1997) for (I); ORTEP-3 (Farrugia, 1997) and CrystMol (Duchamp, 1999) for (II). For both compounds, software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of the molecule of nootkatone (I), showing the atom-numbering scheme and ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. View of one of the two independent molecules of (II), showing the atom-numbering scheme and ellipsoids at the 50% probability level.
[Figure 3] Fig. 3. Stereopair of intermolecular interactions for the B molecule of (II). Carbonyl–carbonyl and Br···Br interactions are dotted and H atoms are not shown.
(I) top
Crystal data top
C15H22OF(000) = 240
Mr = 218.33Dx = 1.119 Mg m3
Monoclinic, P21Melting point: 309-311K K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 5.903 (2) ÅCell parameters from 1493 reflections
b = 9.495 (4) Åθ = 2.5–27.5°
c = 11.630 (6) ŵ = 0.07 mm1
β = 96.09 (2)°T = 150 K
V = 648.2 (5) Å3Needle fragment, colorless
Z = 20.32 × 0.25 × 0.20 mm
Data collection top
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
1202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 2.7°
ω scans with κ offsetsh = 77
7526 measured reflectionsk = 1212
1577 independent reflectionsl = 1515
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)] = 0.041H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0459P)2 + 0.044P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1577 reflectionsΔρmax = 0.16 e Å3
149 parametersΔρmin = 0.15 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.041 (9)
Crystal data top
C15H22OV = 648.2 (5) Å3
Mr = 218.33Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.903 (2) ŵ = 0.07 mm1
b = 9.495 (4) ÅT = 150 K
c = 11.630 (6) Å0.32 × 0.25 × 0.20 mm
β = 96.09 (2)°
Data collection top
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
1202 reflections with I > 2σ(I)
7526 measured reflectionsRint = 0.023
1577 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0411 restraint
wR(F2) = 0.098H-atom parameters constrained
S = 1.06Δρmax = 0.16 e Å3
1577 reflectionsΔρmin = 0.15 e Å3
149 parameters
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
O10.9245 (3)0.4298 (2)0.40302 (15)0.0544 (5)
C10.8374 (4)0.3090 (3)0.56883 (19)0.0324 (5)
H10.91460.22680.54750.039*
C20.8218 (4)0.4282 (3)0.4894 (2)0.0379 (6)
C30.6720 (4)0.5467 (3)0.5196 (2)0.0393 (6)
H3A0.51180.52480.49120.047*
H3B0.71570.63370.48060.047*
C40.6917 (4)0.5713 (2)0.65075 (19)0.0317 (6)
H40.85550.59230.67580.038*
C50.6313 (3)0.4369 (3)0.71613 (18)0.0274 (5)
C60.7166 (4)0.4560 (2)0.84551 (18)0.0287 (5)
H6A0.87550.49080.85140.034*
H6B0.62310.52990.87770.034*
C70.7101 (4)0.3238 (2)0.92099 (19)0.0280 (5)
H70.54860.29030.91480.034*
C80.8507 (4)0.2093 (3)0.8705 (2)0.0343 (6)
H8A0.84460.12220.91690.041*
H8B1.01170.23980.87440.041*
C90.7605 (4)0.1786 (3)0.7443 (2)0.0352 (6)
H9A0.86110.10870.71220.042*
H9B0.60650.13670.74190.042*
C100.7490 (3)0.3088 (2)0.67038 (18)0.0283 (5)
C110.7807 (4)0.3577 (2)1.04696 (19)0.0328 (6)
C120.6291 (4)0.4579 (3)1.1030 (2)0.0431 (7)
H12A0.67550.46121.18640.065*
H12B0.47090.42571.08920.065*
H12C0.64210.55221.07000.065*
C130.9638 (4)0.3046 (3)1.1070 (2)0.0452 (7)
H13A0.99980.32981.18590.054*
H13B1.05930.24121.07120.054*
C140.3711 (4)0.4100 (3)0.7018 (2)0.0397 (6)
H14A0.31480.41100.61940.060*
H14B0.29440.48390.74200.060*
H14C0.33940.31810.73490.060*
C150.5564 (5)0.7019 (3)0.6779 (2)0.0473 (7)
H15A0.61930.78460.64220.071*
H15B0.56650.71520.76190.071*
H15C0.39650.68970.64710.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0656 (12)0.0614 (13)0.0393 (10)0.0189 (11)0.0202 (9)0.0027 (10)
C10.0315 (11)0.0327 (12)0.0330 (12)0.0024 (10)0.0037 (10)0.0046 (11)
C20.0368 (12)0.0485 (16)0.0287 (11)0.0164 (12)0.0044 (10)0.0046 (12)
C30.0409 (13)0.0428 (15)0.0327 (13)0.0061 (12)0.0042 (11)0.0093 (11)
C40.0324 (11)0.0326 (14)0.0290 (12)0.0024 (10)0.0018 (10)0.0046 (10)
C50.0242 (10)0.0287 (11)0.0289 (11)0.0007 (9)0.0020 (9)0.0016 (10)
C60.0312 (11)0.0260 (12)0.0287 (11)0.0003 (9)0.0025 (9)0.0006 (10)
C70.0284 (11)0.0259 (12)0.0298 (11)0.0007 (9)0.0031 (9)0.0002 (10)
C80.0432 (13)0.0256 (12)0.0347 (13)0.0026 (10)0.0064 (11)0.0022 (10)
C90.0459 (14)0.0257 (13)0.0349 (13)0.0003 (11)0.0086 (11)0.0030 (10)
C100.0233 (10)0.0300 (12)0.0312 (12)0.0035 (9)0.0004 (9)0.0002 (10)
C110.0402 (14)0.0270 (12)0.0319 (12)0.0009 (10)0.0076 (11)0.0019 (10)
C120.0556 (16)0.0426 (16)0.0324 (13)0.0069 (13)0.0110 (11)0.0009 (12)
C130.0531 (15)0.0436 (15)0.0371 (13)0.0117 (13)0.0038 (12)0.0007 (13)
C140.0264 (11)0.0484 (17)0.0443 (14)0.0025 (11)0.0031 (10)0.0025 (12)
C150.0597 (17)0.0369 (14)0.0429 (15)0.0118 (13)0.0052 (13)0.0048 (13)
Geometric parameters (Å, º) top
O1—C21.228 (3)C8—C91.534 (3)
C1—C101.341 (3)C8—H8A0.9900
C1—C21.457 (4)C8—H8B0.9900
C1—H10.9500C9—C101.504 (3)
C2—C31.496 (4)C9—H9A0.9900
C3—C41.536 (3)C9—H9B0.9900
C3—H3A0.9900C11—C131.323 (3)
C3—H3B0.9900C11—C121.501 (3)
C4—C151.526 (4)C12—H12A0.9800
C4—C51.546 (3)C12—H12B0.9800
C4—H41.0000C12—H12C0.9800
C5—C101.524 (3)C13—H13A0.9500
C5—C61.546 (3)C13—H13B0.9500
C5—C141.549 (3)C14—H14A0.9800
C6—C71.535 (3)C14—H14B0.9800
C6—H6A0.9900C14—H14C0.9800
C6—H6B0.9900C15—H15A0.9800
C7—C111.515 (3)C15—H15B0.9800
C7—C81.523 (3)C15—H15C0.9800
C7—H71.0000
C10—C1—C2123.7 (2)C9—C8—H8A109.5
C10—C1—H1118.2C7—C8—H8B109.5
C2—C1—H1118.2C9—C8—H8B109.5
O1—C2—C1121.7 (2)H8A—C8—H8B108.1
O1—C2—C3122.5 (2)C10—C9—C8112.37 (19)
C1—C2—C3115.8 (2)C10—C9—H9A109.1
C2—C3—C4111.27 (18)C8—C9—H9A109.1
C2—C3—H3A109.4C10—C9—H9B109.1
C4—C3—H3A109.4C8—C9—H9B109.1
C2—C3—H3B109.4H9A—C9—H9B107.9
C4—C3—H3B109.4C1—C10—C9120.4 (2)
H3A—C3—H3B108.0C1—C10—C5122.8 (2)
C15—C4—C3110.07 (19)C9—C10—C5116.82 (19)
C15—C4—C5114.6 (2)C13—C11—C12120.2 (2)
C3—C4—C5111.48 (19)C13—C11—C7123.7 (2)
C15—C4—H4106.8C12—C11—C7116.05 (19)
C3—C4—H4106.8C11—C12—H12A109.5
C5—C4—H4106.8C11—C12—H12B109.5
C10—C5—C6108.66 (17)H12A—C12—H12B109.5
C10—C5—C4110.44 (16)C11—C12—H12C109.5
C6—C5—C4108.28 (18)H12A—C12—H12C109.5
C10—C5—C14108.32 (19)H12B—C12—H12C109.5
C6—C5—C14109.93 (17)C11—C13—H13A120.0
C4—C5—C14111.17 (19)C11—C13—H13B120.0
C7—C6—C5115.81 (18)H13A—C13—H13B120.0
C7—C6—H6A108.3C5—C14—H14A109.5
C5—C6—H6A108.3C5—C14—H14B109.5
C7—C6—H6B108.3H14A—C14—H14B109.5
C5—C6—H6B108.3C5—C14—H14C109.5
H6A—C6—H6B107.4H14A—C14—H14C109.5
C11—C7—C8114.82 (17)H14B—C14—H14C109.5
C11—C7—C6110.97 (18)C4—C15—H15A109.5
C8—C7—C6108.41 (18)C4—C15—H15B109.5
C11—C7—H7107.4H15A—C15—H15B109.5
C8—C7—H7107.4C4—C15—H15C109.5
C6—C7—H7107.4H15A—C15—H15C109.5
C7—C8—C9110.89 (18)H15B—C15—H15C109.5
C7—C8—H8A109.5
C10—C1—C2—O1172.4 (2)C11—C7—C8—C9177.82 (19)
C10—C1—C2—C38.1 (3)C6—C7—C8—C957.5 (2)
O1—C2—C3—C4142.6 (2)C7—C8—C9—C1055.0 (3)
C1—C2—C3—C437.9 (3)C2—C1—C10—C9176.45 (19)
C2—C3—C4—C15174.2 (2)C2—C1—C10—C52.9 (3)
C2—C3—C4—C557.5 (3)C8—C9—C10—C1130.8 (2)
C15—C4—C5—C10171.74 (19)C8—C9—C10—C549.8 (3)
C3—C4—C5—C1045.9 (2)C6—C5—C10—C1135.4 (2)
C15—C4—C5—C669.4 (2)C4—C5—C10—C116.7 (3)
C3—C4—C5—C6164.77 (18)C14—C5—C10—C1105.2 (2)
C15—C4—C5—C1451.5 (3)C6—C5—C10—C945.3 (2)
C3—C4—C5—C1474.4 (2)C4—C5—C10—C9163.92 (18)
C10—C5—C6—C749.6 (2)C14—C5—C10—C974.1 (2)
C4—C5—C6—C7169.61 (18)C8—C7—C11—C136.8 (3)
C14—C5—C6—C768.8 (3)C6—C7—C11—C13116.5 (3)
C5—C6—C7—C11175.80 (18)C8—C7—C11—C12173.2 (2)
C5—C6—C7—C857.2 (2)C6—C7—C11—C1263.4 (2)
(II) top
Crystal data top
C15H24Br2OF(000) = 768
Mr = 380.16Dx = 1.612 Mg m3
Monoclinic, P21Melting point: 406-408K K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 13.500 (3) ÅCell parameters from 4844 reflections
b = 6.1403 (10) Åθ = 2.5–30.5°
c = 18.909 (5) ŵ = 5.16 mm1
β = 92.145 (7)°T = 100 K
V = 1566.3 (6) Å3Needle, colorless
Z = 40.30 × 0.05 × 0.02 mm
Data collection top
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
9388 independent reflections
Radiation source: fine-focus sealed tube7482 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ω scans with κ offsetsθmax = 30.5°, θmin = 3.0°
Absorption correction: multi-scan
(HKL SCALEPACK; Otwinowski & Minor, 1997)
h = 1919
Tmin = 0.385, Tmax = 0.902k = 88
19375 measured reflectionsl = 2726
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)] = 0.053H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + 4.911P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
9388 reflectionsΔρmax = 1.09 e Å3
333 parametersΔρmin = 0.66 e Å3
1 restraintAbsolute structure: Flack (1983), 4216 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.019 (11)
Crystal data top
C15H24Br2OV = 1566.3 (6) Å3
Mr = 380.16Z = 4
Monoclinic, P21Mo Kα radiation
a = 13.500 (3) ŵ = 5.16 mm1
b = 6.1403 (10) ÅT = 100 K
c = 18.909 (5) Å0.30 × 0.05 × 0.02 mm
β = 92.145 (7)°
Data collection top
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
9388 independent reflections
Absorption correction: multi-scan
(HKL SCALEPACK; Otwinowski & Minor, 1997)
7482 reflections with I > 2σ(I)
Tmin = 0.385, Tmax = 0.902Rint = 0.063
19375 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.095Δρmax = 1.09 e Å3
S = 1.10Δρmin = 0.66 e Å3
9388 reflectionsAbsolute structure: Flack (1983), 4216 Friedel pairs
333 parametersAbsolute structure parameter: 0.019 (11)
1 restraint
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
Br1A0.31947 (3)0.63431 (9)0.38734 (3)0.02530 (12)
Br2A0.71950 (3)0.65096 (9)0.46932 (3)0.02331 (11)
O1A0.5042 (3)0.7030 (5)0.47129 (19)0.0210 (8)
C1A0.4379 (3)0.4506 (7)0.3845 (3)0.0161 (10)
H1A0.42180.30720.40640.019*
C2A0.5197 (3)0.5570 (7)0.4304 (3)0.0155 (9)
C3A0.6222 (3)0.4556 (7)0.4236 (2)0.0145 (9)
H3A0.62290.31800.45190.017*
C4A0.6501 (3)0.3935 (9)0.3483 (2)0.0153 (8)
H4A0.65900.53180.32130.018*
C5A0.5647 (3)0.2638 (7)0.3104 (3)0.0135 (9)
C6A0.5925 (4)0.2194 (8)0.2334 (3)0.0196 (10)
H6A10.61240.35870.21170.024*
H6A20.65080.12160.23390.024*
C7A0.5095 (3)0.1164 (8)0.1864 (2)0.0190 (10)
H7A0.49120.02490.20870.023*
C8A0.4182 (4)0.2649 (8)0.1875 (3)0.0233 (11)
H8A10.43370.40550.16480.028*
H8A20.36300.19630.15970.028*
C9A0.3859 (3)0.3066 (8)0.2625 (3)0.0186 (10)
H9A10.36500.16740.28370.022*
H9A20.32810.40600.26090.022*
C10A0.4695 (3)0.4077 (9)0.3095 (2)0.0148 (8)
H10A0.48680.55130.28820.018*
C11A0.5450 (4)0.0648 (9)0.1117 (3)0.0241 (11)
H11A0.57550.20020.09280.029*
C12A0.6244 (4)0.1118 (13)0.1140 (3)0.0372 (14)
H12A0.59870.24220.13690.056*
H12B0.68300.05910.14090.056*
H12C0.64250.14770.06570.056*
C13A0.4611 (4)0.0035 (11)0.0597 (3)0.0337 (14)
H13A0.48810.03190.01320.050*
H13B0.41190.11360.05560.050*
H13C0.42950.13590.07700.050*
C14A0.5487 (4)0.0440 (7)0.3484 (3)0.0180 (10)
H14A0.48980.02810.32750.027*
H14B0.53930.07020.39880.027*
H14C0.60680.04930.34280.027*
C15A0.7499 (4)0.2750 (9)0.3515 (3)0.0220 (10)
H15A0.74280.13550.37600.033*
H15B0.79930.36480.37720.033*
H15C0.77150.24870.30330.033*
Br1B0.18748 (3)0.40480 (9)0.09903 (3)0.02568 (11)
Br2B0.21533 (3)0.40203 (11)0.04876 (3)0.02671 (12)
O1B0.0012 (3)0.3464 (5)0.02916 (19)0.0216 (8)
C1B0.0709 (3)0.5932 (7)0.1113 (3)0.0159 (10)
H1B0.08710.73640.08860.019*
C2B0.0140 (4)0.4910 (7)0.0715 (3)0.0161 (9)
C3B0.1152 (3)0.5943 (7)0.0865 (2)0.0145 (9)
H3B0.11670.73190.05830.017*
C4B0.1396 (3)0.6571 (9)0.1641 (2)0.0149 (8)
H4B0.14770.51930.19190.018*
C5B0.0514 (3)0.7868 (7)0.1950 (3)0.0149 (9)
C6B0.0746 (3)0.8319 (7)0.2737 (3)0.0160 (9)
H6B10.13200.93180.27800.019*
H6B20.09380.69350.29730.019*
C7B0.0126 (3)0.9326 (8)0.3124 (2)0.0183 (10)
H7B0.03321.06620.28540.022*
C8B0.0995 (4)0.7742 (8)0.3068 (3)0.0216 (10)
H8B10.08070.63540.33040.026*
H8B20.15660.83590.33140.026*
C9B0.1293 (4)0.7307 (8)0.2297 (3)0.0204 (10)
H9B10.15150.86840.20690.024*
H9B20.18570.62740.22730.024*
C10B0.0433 (3)0.6359 (9)0.1893 (2)0.0148 (8)
H10B0.02520.49300.21150.018*
C11B0.0138 (4)1.0057 (8)0.3891 (3)0.0213 (11)
H11B0.04901.05960.40930.026*
C12B0.0518 (4)0.8221 (8)0.4373 (3)0.0236 (11)
H12D0.11550.76950.42080.035*
H12E0.00380.70230.43620.035*
H12F0.06060.87660.48580.035*
C13B0.0860 (4)1.1991 (9)0.3898 (3)0.0314 (13)
H13D0.09541.25370.43830.047*
H13E0.05871.31530.35940.047*
H13F0.14991.15170.37230.047*
C14B0.0340 (4)1.0032 (7)0.1551 (3)0.0185 (10)
H14D0.02981.06490.16780.028*
H14E0.03370.97650.10400.028*
H14F0.08731.10560.16830.028*
C15B0.2377 (4)0.7796 (9)0.1696 (3)0.0207 (10)
H15D0.28950.69210.14830.031*
H15E0.25580.80650.21950.031*
H15F0.23100.91880.14460.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0172 (2)0.0302 (3)0.0285 (3)0.0093 (2)0.00145 (18)0.0048 (3)
Br2A0.0201 (2)0.0270 (2)0.0225 (2)0.0045 (2)0.00245 (18)0.0052 (2)
O1A0.0268 (18)0.0178 (17)0.0185 (18)0.0024 (14)0.0034 (15)0.0039 (14)
C1A0.012 (2)0.016 (2)0.020 (2)0.0058 (17)0.0015 (17)0.0010 (18)
C2A0.014 (2)0.016 (2)0.017 (2)0.0019 (18)0.0002 (18)0.0055 (19)
C3A0.014 (2)0.013 (2)0.016 (2)0.0021 (16)0.0011 (17)0.0004 (17)
C4A0.0152 (19)0.015 (2)0.015 (2)0.002 (2)0.0006 (15)0.002 (2)
C5A0.014 (2)0.013 (2)0.014 (2)0.0001 (17)0.0005 (17)0.0006 (18)
C6A0.018 (2)0.024 (2)0.017 (3)0.0019 (19)0.0055 (18)0.001 (2)
C7A0.021 (2)0.018 (2)0.017 (2)0.002 (2)0.0017 (17)0.002 (2)
C8A0.024 (3)0.022 (3)0.023 (3)0.000 (2)0.005 (2)0.001 (2)
C9A0.014 (2)0.024 (2)0.017 (3)0.0033 (19)0.0012 (18)0.004 (2)
C10A0.0175 (19)0.0141 (19)0.013 (2)0.004 (2)0.0015 (15)0.002 (2)
C11A0.028 (3)0.029 (3)0.016 (3)0.001 (2)0.002 (2)0.000 (2)
C12A0.032 (3)0.054 (4)0.026 (3)0.009 (3)0.001 (2)0.011 (3)
C13A0.035 (3)0.047 (3)0.019 (3)0.000 (3)0.001 (2)0.003 (3)
C14A0.020 (2)0.014 (2)0.021 (3)0.0016 (18)0.001 (2)0.0021 (19)
C15A0.019 (2)0.022 (2)0.025 (3)0.0008 (19)0.0008 (19)0.007 (2)
Br1B0.0182 (2)0.0256 (2)0.0330 (3)0.0054 (2)0.00305 (19)0.0070 (3)
Br2B0.0232 (2)0.0346 (3)0.0224 (3)0.0103 (3)0.00155 (18)0.0071 (3)
O1B0.0277 (18)0.0182 (18)0.0187 (19)0.0012 (14)0.0019 (15)0.0008 (14)
C1B0.016 (2)0.012 (2)0.020 (2)0.0019 (16)0.0022 (17)0.0010 (17)
C2B0.021 (2)0.015 (2)0.012 (2)0.0007 (19)0.0023 (18)0.0026 (19)
C3B0.016 (2)0.016 (2)0.011 (2)0.0092 (17)0.0034 (16)0.0021 (17)
C4B0.0157 (19)0.016 (2)0.012 (2)0.004 (2)0.0034 (15)0.003 (2)
C5B0.014 (2)0.015 (2)0.016 (2)0.0008 (17)0.0009 (18)0.0015 (19)
C6B0.015 (2)0.014 (2)0.018 (2)0.0014 (17)0.0008 (18)0.0011 (18)
C7B0.024 (2)0.019 (2)0.012 (2)0.000 (2)0.0018 (17)0.0029 (19)
C8B0.019 (2)0.024 (3)0.022 (3)0.001 (2)0.003 (2)0.003 (2)
C9B0.015 (2)0.022 (2)0.025 (3)0.0034 (19)0.0018 (19)0.002 (2)
C10B0.0153 (19)0.0134 (19)0.015 (2)0.000 (2)0.0000 (15)0.000 (2)
C11B0.020 (2)0.023 (2)0.021 (3)0.003 (2)0.001 (2)0.006 (2)
C12B0.030 (3)0.026 (3)0.015 (3)0.004 (2)0.003 (2)0.002 (2)
C13B0.042 (3)0.027 (3)0.025 (3)0.004 (2)0.006 (2)0.000 (2)
C14B0.023 (2)0.012 (2)0.020 (3)0.0002 (18)0.002 (2)0.0004 (19)
C15B0.018 (2)0.027 (3)0.017 (3)0.001 (2)0.0010 (19)0.001 (2)
Geometric parameters (Å, º) top
Br1A—C1A1.959 (4)Br1B—C1B1.960 (4)
Br2A—C3A1.956 (4)Br2B—C3B1.950 (4)
O1A—C2A1.207 (6)O1B—C2B1.203 (6)
C1A—C10A1.520 (6)C1B—C10B1.529 (6)
C1A—C2A1.526 (6)C1B—C2B1.530 (7)
C1A—H1A1.0000C1B—H1B1.0000
C2A—C3A1.527 (6)C2B—C3B1.523 (6)
C3A—C4A1.535 (6)C3B—C4B1.542 (6)
C3A—H3A1.0000C3B—H3B1.0000
C4A—C15A1.530 (6)C4B—C15B1.523 (6)
C4A—C5A1.554 (6)C4B—C5B1.564 (6)
C4A—H4A1.0000C4B—H4B1.0000
C5A—C6A1.543 (7)C5B—C6B1.535 (7)
C5A—C14A1.547 (6)C5B—C14B1.541 (6)
C5A—C10A1.560 (6)C5B—C10B1.579 (6)
C6A—C7A1.540 (7)C6B—C7B1.538 (6)
C6A—H6A10.9900C6B—H6B10.9900
C6A—H6A20.9900C6B—H6B20.9900
C7A—C8A1.533 (7)C7B—C8B1.525 (7)
C7A—C11A1.541 (7)C7B—C11B1.547 (7)
C7A—H7A1.0000C7B—H7B1.0000
C8A—C9A1.521 (7)C8B—C9B1.522 (7)
C8A—H8A10.9900C8B—H8B10.9900
C8A—H8A20.9900C8B—H8B20.9900
C9A—C10A1.540 (6)C9B—C10B1.529 (6)
C9A—H9A10.9900C9B—H9B10.9900
C9A—H9A20.9900C9B—H9B20.9900
C10A—H10A1.0000C10B—H10B1.0000
C11A—C12A1.524 (8)C11B—C12B1.527 (7)
C11A—C13A1.531 (8)C11B—C13B1.536 (7)
C11A—H11A1.0000C11B—H11B1.0000
C12A—H12A0.9800C12B—H12D0.9800
C12A—H12B0.9800C12B—H12E0.9800
C12A—H12C0.9800C12B—H12F0.9800
C13A—H13A0.9800C13B—H13D0.9800
C13A—H13B0.9800C13B—H13E0.9800
C13A—H13C0.9800C13B—H13F0.9800
C14A—H14A0.9800C14B—H14D0.9800
C14A—H14B0.9800C14B—H14E0.9800
C14A—H14C0.9800C14B—H14F0.9800
C15A—H15A0.9800C15B—H15D0.9800
C15A—H15B0.9800C15B—H15E0.9800
C15A—H15C0.9800C15B—H15F0.9800
C10A—C1A—C2A112.5 (4)C10B—C1B—C2B112.7 (4)
C10A—C1A—Br1A112.5 (3)C10B—C1B—Br1B112.4 (3)
C2A—C1A—Br1A108.2 (3)C2B—C1B—Br1B108.2 (3)
C10A—C1A—H1A107.8C10B—C1B—H1B107.8
C2A—C1A—H1A107.8C2B—C1B—H1B107.8
Br1A—C1A—H1A107.8Br1B—C1B—H1B107.8
O1A—C2A—C1A122.9 (4)O1B—C2B—C3B122.4 (4)
O1A—C2A—C3A122.5 (4)O1B—C2B—C1B122.6 (4)
C1A—C2A—C3A114.6 (4)C3B—C2B—C1B114.9 (4)
C2A—C3A—C4A115.7 (4)C2B—C3B—C4B116.1 (4)
C2A—C3A—Br2A107.9 (3)C2B—C3B—Br2B108.0 (3)
C4A—C3A—Br2A112.2 (3)C4B—C3B—Br2B111.9 (3)
C2A—C3A—H3A106.8C2B—C3B—H3B106.8
C4A—C3A—H3A106.8C4B—C3B—H3B106.8
Br2A—C3A—H3A106.8Br2B—C3B—H3B106.8
C15A—C4A—C3A109.1 (4)C15B—C4B—C3B110.0 (4)
C15A—C4A—C5A114.3 (4)C15B—C4B—C5B113.3 (4)
C3A—C4A—C5A110.6 (3)C3B—C4B—C5B110.1 (3)
C15A—C4A—H4A107.5C15B—C4B—H4B107.7
C3A—C4A—H4A107.5C3B—C4B—H4B107.7
C5A—C4A—H4A107.5C5B—C4B—H4B107.7
C6A—C5A—C14A109.1 (4)C6B—C5B—C14B109.9 (4)
C6A—C5A—C4A108.9 (4)C6B—C5B—C4B108.9 (4)
C14A—C5A—C4A110.4 (4)C14B—C5B—C4B111.1 (4)
C6A—C5A—C10A108.6 (4)C6B—C5B—C10B107.9 (4)
C14A—C5A—C10A111.7 (4)C14B—C5B—C10B111.4 (4)
C4A—C5A—C10A108.2 (4)C4B—C5B—C10B107.5 (4)
C7A—C6A—C5A114.8 (4)C5B—C6B—C7B113.7 (4)
C7A—C6A—H6A1108.6C5B—C6B—H6B1108.8
C5A—C6A—H6A1108.6C7B—C6B—H6B1108.8
C7A—C6A—H6A2108.6C5B—C6B—H6B2108.8
C5A—C6A—H6A2108.6C7B—C6B—H6B2108.8
H6A1—C6A—H6A2107.5H6B1—C6B—H6B2107.7
C8A—C7A—C6A108.4 (4)C8B—C7B—C6B108.2 (4)
C8A—C7A—C11A114.3 (4)C8B—C7B—C11B113.5 (4)
C6A—C7A—C11A111.6 (4)C6B—C7B—C11B114.1 (4)
C8A—C7A—H7A107.4C8B—C7B—H7B106.9
C6A—C7A—H7A107.4C6B—C7B—H7B106.9
C11A—C7A—H7A107.4C11B—C7B—H7B106.9
C9A—C8A—C7A111.8 (4)C9B—C8B—C7B110.7 (4)
C9A—C8A—H8A1109.3C9B—C8B—H8B1109.5
C7A—C8A—H8A1109.3C7B—C8B—H8B1109.5
C9A—C8A—H8A2109.3C9B—C8B—H8B2109.5
C7A—C8A—H8A2109.3C7B—C8B—H8B2109.5
H8A1—C8A—H8A2107.9H8B1—C8B—H8B2108.1
C8A—C9A—C10A112.1 (4)C8B—C9B—C10B111.5 (4)
C8A—C9A—H9A1109.2C8B—C9B—H9B1109.3
C10A—C9A—H9A1109.2C10B—C9B—H9B1109.3
C8A—C9A—H9A2109.2C8B—C9B—H9B2109.3
C10A—C9A—H9A2109.2C10B—C9B—H9B2109.3
H9A1—C9A—H9A2107.9H9B1—C9B—H9B2108.0
C1A—C10A—C9A112.5 (4)C1B—C10B—C9B112.6 (4)
C1A—C10A—C5A110.3 (3)C1B—C10B—C5B109.5 (4)
C9A—C10A—C5A111.4 (4)C9B—C10B—C5B111.8 (4)
C1A—C10A—H10A107.5C1B—C10B—H10B107.6
C9A—C10A—H10A107.5C9B—C10B—H10B107.6
C5A—C10A—H10A107.5C5B—C10B—H10B107.6
C12A—C11A—C13A109.0 (5)C12B—C11B—C13B111.5 (4)
C12A—C11A—C7A111.3 (4)C12B—C11B—C7B114.0 (4)
C13A—C11A—C7A113.4 (4)C13B—C11B—C7B110.9 (4)
C12A—C11A—H11A107.6C12B—C11B—H11B106.7
C13A—C11A—H11A107.6C13B—C11B—H11B106.7
C7A—C11A—H11A107.6C7B—C11B—H11B106.7
C11A—C12A—H12A109.5C11B—C12B—H12D109.5
C11A—C12A—H12B109.5C11B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
C11A—C12A—H12C109.5C11B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
C11A—C13A—H13A109.5C11B—C13B—H13D109.5
C11A—C13A—H13B109.5C11B—C13B—H13E109.5
H13A—C13A—H13B109.5H13D—C13B—H13E109.5
C11A—C13A—H13C109.5C11B—C13B—H13F109.5
H13A—C13A—H13C109.5H13D—C13B—H13F109.5
H13B—C13A—H13C109.5H13E—C13B—H13F109.5
C5A—C14A—H14A109.5C5B—C14B—H14D109.5
C5A—C14A—H14B109.5C5B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
C5A—C14A—H14C109.5C5B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
C4A—C15A—H15A109.5C4B—C15B—H15D109.5
C4A—C15A—H15B109.5C4B—C15B—H15E109.5
H15A—C15A—H15B109.5H15D—C15B—H15E109.5
C4A—C15A—H15C109.5C4B—C15B—H15F109.5
H15A—C15A—H15C109.5H15D—C15B—H15F109.5
H15B—C15A—H15C109.5H15E—C15B—H15F109.5
C10A—C1A—C2A—O1A138.4 (5)C10B—C1B—C2B—O1B138.6 (5)
Br1A—C1A—C2A—O1A13.5 (6)Br1B—C1B—C2B—O1B13.7 (6)
C10A—C1A—C2A—C3A44.8 (5)C10B—C1B—C2B—C3B44.4 (5)
Br1A—C1A—C2A—C3A169.8 (3)Br1B—C1B—C2B—C3B169.4 (3)
O1A—C2A—C3A—C4A142.1 (5)O1B—C2B—C3B—C4B142.6 (4)
C1A—C2A—C3A—C4A41.1 (6)C1B—C2B—C3B—C4B40.5 (5)
O1A—C2A—C3A—Br2A15.4 (6)O1B—C2B—C3B—Br2B16.0 (5)
C1A—C2A—C3A—Br2A167.8 (3)C1B—C2B—C3B—Br2B167.1 (3)
C2A—C3A—C4A—C15A174.6 (4)C2B—C3B—C4B—C15B174.0 (4)
Br2A—C3A—C4A—C15A60.9 (5)Br2B—C3B—C4B—C15B61.4 (5)
C2A—C3A—C4A—C5A48.1 (5)C2B—C3B—C4B—C5B48.4 (5)
Br2A—C3A—C4A—C5A172.6 (3)Br2B—C3B—C4B—C5B173.0 (3)
C15A—C4A—C5A—C6A60.5 (5)C15B—C4B—C5B—C6B60.5 (5)
C3A—C4A—C5A—C6A175.9 (4)C3B—C4B—C5B—C6B175.8 (4)
C15A—C4A—C5A—C14A59.2 (5)C15B—C4B—C5B—C14B60.7 (5)
C3A—C4A—C5A—C14A64.4 (5)C3B—C4B—C5B—C14B63.0 (5)
C15A—C4A—C5A—C10A178.3 (4)C15B—C4B—C5B—C10B177.2 (4)
C3A—C4A—C5A—C10A58.1 (5)C3B—C4B—C5B—C10B59.1 (5)
C14A—C5A—C6A—C7A66.7 (5)C14B—C5B—C6B—C7B65.6 (5)
C4A—C5A—C6A—C7A172.8 (4)C4B—C5B—C6B—C7B172.5 (4)
C10A—C5A—C6A—C7A55.3 (5)C10B—C5B—C6B—C7B56.0 (5)
C5A—C6A—C7A—C8A56.6 (5)C5B—C6B—C7B—C8B60.0 (5)
C5A—C6A—C7A—C11A176.6 (4)C5B—C6B—C7B—C11B172.6 (4)
C6A—C7A—C8A—C9A55.7 (5)C6B—C7B—C8B—C9B59.1 (5)
C11A—C7A—C8A—C9A179.1 (4)C11B—C7B—C8B—C9B173.2 (4)
C7A—C8A—C9A—C10A57.4 (5)C7B—C8B—C9B—C10B58.9 (6)
C2A—C1A—C10A—C9A178.3 (4)C2B—C1B—C10B—C9B178.0 (4)
Br1A—C1A—C10A—C9A55.8 (5)Br1B—C1B—C10B—C9B55.4 (5)
C2A—C1A—C10A—C5A56.7 (5)C2B—C1B—C10B—C5B57.0 (5)
Br1A—C1A—C10A—C5A179.2 (3)Br1B—C1B—C10B—C5B179.6 (3)
C8A—C9A—C10A—C1A179.9 (4)C8B—C9B—C10B—C1B179.3 (4)
C8A—C9A—C10A—C5A55.7 (5)C8B—C9B—C10B—C5B55.5 (5)
C6A—C5A—C10A—C1A178.6 (4)C6B—C5B—C10B—C1B178.2 (4)
C14A—C5A—C10A—C1A58.2 (5)C14B—C5B—C10B—C1B57.5 (5)
C4A—C5A—C10A—C1A63.5 (5)C4B—C5B—C10B—C1B64.5 (5)
C6A—C5A—C10A—C9A52.9 (5)C6B—C5B—C10B—C9B52.6 (5)
C14A—C5A—C10A—C9A67.5 (5)C14B—C5B—C10B—C9B68.1 (5)
C4A—C5A—C10A—C9A170.8 (4)C4B—C5B—C10B—C9B169.9 (4)
C8A—C7A—C11A—C12A170.6 (5)C8B—C7B—C11B—C12B65.2 (6)
C6A—C7A—C11A—C12A65.9 (6)C6B—C7B—C11B—C12B59.3 (6)
C8A—C7A—C11A—C13A47.2 (6)C8B—C7B—C11B—C13B168.0 (4)
C6A—C7A—C11A—C13A170.8 (5)C6B—C7B—C11B—C13B67.4 (5)

Experimental details

(I)(II)
Crystal data
Chemical formulaC15H22OC15H24Br2O
Mr218.33380.16
Crystal system, space groupMonoclinic, P21Monoclinic, P21
Temperature (K)150100
a, b, c (Å)5.903 (2), 9.495 (4), 11.630 (6)13.500 (3), 6.1403 (10), 18.909 (5)
β (°) 96.09 (2) 92.145 (7)
V3)648.2 (5)1566.3 (6)
Z24
Radiation typeMo KαMo Kα
µ (mm1)0.075.16
Crystal size (mm)0.32 × 0.25 × 0.200.30 × 0.05 × 0.02
Data collection
DiffractometerNonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
Absorption correctionMulti-scan
(HKL SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.385, 0.902
No. of measured, independent and
observed [I > 2σ(I)] reflections
7526, 1577, 1202 19375, 9388, 7482
Rint0.0230.063
(sin θ/λ)max1)0.6500.714
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.098, 1.06 0.053, 0.095, 1.10
No. of reflections15779388
No. of parameters149333
No. of restraints11
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.151.09, 0.66
Absolute structure?Flack (1983), 4216 Friedel pairs
Absolute structure parameter?0.019 (11)

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and CrystMol (Duchamp, 1999), SHELXL97.

Selected geometric parameters (Å, º) for (I) top
O1—C21.228 (3)C11—C131.323 (3)
C1—C101.341 (3)C11—C121.501 (3)
C1—C21.457 (4)
C10—C1—C2—C38.1 (3)C7—C8—C9—C1055.0 (3)
C1—C2—C3—C437.9 (3)C2—C1—C10—C52.9 (3)
C2—C3—C4—C557.5 (3)C8—C9—C10—C549.8 (3)
C3—C4—C5—C1045.9 (2)C4—C5—C10—C116.7 (3)
C10—C5—C6—C749.6 (2)C6—C5—C10—C945.3 (2)
C5—C6—C7—C857.2 (2)C6—C7—C11—C1263.4 (2)
C6—C7—C8—C957.5 (2)
Selected geometric parameters (Å, º) for (II) top
Br1A—C1A1.959 (4)Br1B—C1B1.960 (4)
Br2A—C3A1.956 (4)Br2B—C3B1.950 (4)
O1A—C2A1.207 (6)O1B—C2B1.203 (6)
C10A—C1A—C2A—C3A44.8 (5)C10B—C1B—C2B—C3B44.4 (5)
C1A—C2A—C3A—C4A41.1 (6)C1B—C2B—C3B—C4B40.5 (5)
C2A—C3A—C4A—C5A48.1 (5)C2B—C3B—C4B—C5B48.4 (5)
C3A—C4A—C5A—C10A58.1 (5)C3B—C4B—C5B—C10B59.1 (5)
C10A—C5A—C6A—C7A55.3 (5)C10B—C5B—C6B—C7B56.0 (5)
C5A—C6A—C7A—C8A56.6 (5)C5B—C6B—C7B—C8B60.0 (5)
C6A—C7A—C8A—C9A55.7 (5)C6B—C7B—C8B—C9B59.1 (5)
C7A—C8A—C9A—C10A57.4 (5)C7B—C8B—C9B—C10B58.9 (6)
C2A—C1A—C10A—C5A56.7 (5)C2B—C1B—C10B—C5B57.0 (5)
C8A—C9A—C10A—C5A55.7 (5)C8B—C9B—C10B—C5B55.5 (5)
C4A—C5A—C10A—C1A63.5 (5)C4B—C5B—C10B—C1B64.5 (5)
C6A—C5A—C10A—C9A52.9 (5)C6B—C5B—C10B—C9B52.6 (5)
C6A—C7A—C11A—C12A65.9 (6)C6B—C7B—C11B—C12B59.3 (6)
 

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