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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 3| March 2011| Pages o733-o734

[(2R,5R,6S,9R)-6-Iso­propyl-9-methyl-1,4-dioxa­spiro­[4.5]decan-2-yl]methyl 4-bromo­benzoate

aDepartment of Chemistry and Physics, Mansfield University, Mansfield, PA 16933, USA, and bYoungstown State University, One University Plaza, Youngstown, Ohio 44555-3663, USA
*Correspondence e-mail: akiessli@mansfield.edu

(Received 1 February 2011; accepted 20 February 2011; online 26 February 2011)

The title compound, C20H27BrO4, a 4-bromo­benzoyl derivative of a stereoisomer of glycerol menthonide, synthesized as part of a study of 3-carbon stereochemical moieties, crystallizes with two crystallographically independent mol­ecules in the asymmetric unit, the two mol­ecules differing only in one of the C—O—C—C torsion angles around the ester O atom [−106.5 (7) and 146.1 (6)°]. The two mol­ecules are crystallographically related by a pseudotranslation along the (011) diagonal of the unit cell, emulating a primitive monoclinic cell of half the volume. The translational symmetry is broken by the 4-bromo­benzoate groups. The crystallographic assignment of the absolute stereochemistry is consistent with having started with (−)-menthone, the acetal C atom is R and the secondary alcohol is R. This brings the bromo­benzoate into approximately the same plane as the menthyl ring and cis to the isopropyl group. The glycerol menthonide sections of the molecules interact with each other via C—H⋯O interactions, leading to the formation of chains either A or B molecules that stretch parallel to [010], forming column-shaped double chains. Interactions between neighboring columns are limited to van der Waals contacts.

Related literature

For the original synthesis of glycerol menthonides, see: Greenberg (1999[Greenberg, M. (1999). US Patent No. 5 977 166, Nov. 2.]). For general background to glycerol menthonides, see: Kiessling et al. (2009b[Kiessling, A., Ganong, C. & Johnson, A. (2009b). Am. J. Undergrad. Res. 8, 1-6.]). For a related structure, see: Kiessling et al. (2009a[Kiessling, A., Campana, C. & Kastner, M. E. (2009a). Acta Cryst. E65, o1540.]).

[Scheme 1]

Experimental

Crystal data
  • C20H27BrO4

  • Mr = 411.33

  • Monoclinic, C 2

  • a = 42.976 (7) Å

  • b = 5.5763 (9) Å

  • c = 16.072 (3) Å

  • β = 92.618 (2)°

  • V = 3847.5 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.16 mm−1

  • T = 100 K

  • 0.50 × 0.05 × 0.03 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.588, Tmax = 0.746

  • 17537 measured reflections

  • 9230 independent reflections

  • 6765 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.148

  • S = 1.02

  • 9230 reflections

  • 457 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 4.00 e Å−3

  • Δρmin = −0.75 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3965 Friedel pairs

  • Flack parameter: 0.000 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3A—H3A⋯O1Bi 0.95 2.61 3.295 (8) 129
C13B—H13B⋯O3Bi 1.00 2.69 3.541 (6) 143
C15B—H15C⋯O3Bi 0.99 2.62 3.484 (6) 145
C8A—H8A1⋯O4Aii 0.99 2.68 3.452 (8) 135
C15A—H15A⋯O3Ai 0.99 2.59 3.486 (6) 150
C3B—H3B⋯O1Aii 0.95 2.51 3.195 (8) 129
C8B—H8B1⋯O4Bii 0.99 2.56 3.394 (8) 143
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL and Mercury.

Supporting information


Comment top

The title structure was synthesized as part of a study of 3-carbon stereochemical moieties, specifically tri-substituted glycerol. Here menthone serves as a chiral auxiliary, freezing two carbons into a specific stereochemistry and influencing the stereochemistry of the third owing to the steric bulk of the menthone (Kiessling et al., 2009b). Previously a different stereoisomer was isolated as the 3,5-dinitrobenzoate derivative and its crystal structure was published (Kiessling et al., 2009a).

The starting material, glycerol menthonide, was originally prepared as an additive to spearmint gum by reaction of menthone with glycerol under acid catalysis (Greenberg, 1999). No further chemical analysis of the menthonide had been reported in the literature at that time. Later analysis revealed that glycerol menthonide exists in as many as six isomers, which proved to be difficult to separate (Kiessling et al. 2009b). However, conversion of the hydroxy group to an ester by reaction with 4-bromobenzoyl chloride yields a mixture of esters out of which the title compound crystallizes. Isolation of the crystals followed by sequential recrystallization from methanol/water yielded the title compound in > 97% purity in the form of colorless needles.

The title compound crystallizes with two crystallographically independent molecules in a monoclinic setting in the space group C2, Fig. 1. The two molecules, molecule A and B, are chemically identical and differ only in one on the torsion angles around the ester oxygen atom, C9—C8—O2—C1, which is -106.5 (7) ° in molecule A, and 146.1 (6) ° in molecule B. All other bonds, angles and torsion angles in both molecules are virtually identical, as can be seen in the overlay of the two molecules as shown in Fig. 2, and are within their expected ranges. The two molecules are not only very similar with respect to each other, they are also crystallographically related by a pseudotranslation found along the (0 1 1) diagonal of the unit cell (Fig. 3.). The glycerol menthonide of the two molecules are transformed into each other by a translation of half a unit cell along this direction. The p-bromo benzoate moieties, however, do not obey the pseudotranslation, thus causing a doubling of the unit cell with respect to a theoretical smaller primitive monoclinic cell with the dimensions a = 22.5949, b = 5.5763, c = 16.0718 and β = 108.193.

Packing in the structure of the title molecule is dominated by a combination weak interactions and van der Waals interactions. Via pairs of bifurcated C—H···O interactions between phenyl H atoms and the ester carbonyl O atoms molecules A and B form dimers (Fig. 4, Table 1). The dimers have local non-crystallographic inversion symmetry with the p-bromo benzoate moieties of the A and B molecules related by a pseudo inversion center in the middle of each dimer. The glycerol menthonide sections of the molecules are also interacting with each other with both oxygen atoms of the gylcerol units acting as acceptors for weak C—H···O interactions from aliphatic C—H and CH2 groups of neighboring glycerol menthonide moieties (Table 1). The connections are between like molecules and to both sides of the molecules, which leads to the formation of chains of molecules of either A or B that stretch parallel to the (0 1 0) direction. The combination of both types of C—H···O interactions leads to the formation of column shaped double chains as shown in Fig. 4. The outside of these columns is dominated by methyl, methylene and aromatic H atoms and the bromine atoms, and interactions between neighboring columns are limited to van der Waals interactions.

The refined Flack parameter of 0.000 (13) confirms the compound as a chiral and enantiopure molecule. The crystallographic assignment of the absolute stereochemistry is consistent with having started with (-)-menthone, and provides the stereochemistry of the acetal carbon and the esterified secondary alcohol of the glycerol chain. Specifically, the acetal carbon, C5, is R and the secondary alcohol, C2, is also R. This brings the bromobenzoate into approximately the same plane as the menthyl ring and cis to the isopropyl group.

Related literature top

For the original synthesis of glycerol menthonides, see: Greenberg (1999). For general background to glycerol menthonides, see: Kiessling et al. (2009b). For a related structure, see: Kiessling et al. (2009a).

Experimental top

All chemicals were purchased through ThermoFisher Inc. and used without further purification. Glycerol menthonide was prepared according to the published procedure (Greenberg 1999). GC/MS data was obtained using a Varian CP 3800 with Saturn 2000 ion trap MS. Column: Varian CP 5860, WCOT fused silica 30 m × 0.25 mm, coating CP-Sil. Carrier gas: He 1.2 ml/min. Temperature Program: initial temperature 473 K, ramp 20 K/min to 533 K hold 14.5 min. NMR data were obtained at Bucknell University using a Varian 600 MHz instrument and CDCl3, data are reported as p.p.m. from TMS and coupling constants are in Hz. Melting points were obtained on a MelTemp and are uncorrected. TLC was done with Analtech 2520 plates.

In a 50-ml round-bottom flask were placed glycerol menthonide (5.02 g, 22.0 mmol), 4-bromobenzoyl chloride (4.96 g, 23.0 mmol) and pyridine (10 ml). The flask was fitted with an air reflux condenser, drying tube and a magnetic stir bar. The flask was heated to reflux of the solvent while stirring for 2 h. The contents of the flask were then added to water (30 ml) and methyl tert-butyl ether (MTBE, 20 ml) and separated. The aqueous layer was extracted twice with MTBE (20 ml). The combined organic layers were washed with 10% HCl (2 × 15 ml), 10% Na2CO3 (2 × 15 ml) and saturated NaCl (15 ml), dried over MgSO4 and the solvent removed under vacuum to yield the crude product as an oil. To the oil was added methanol (10 ml) and the solution placed in a freezer for 72 hr. Vacuum filtration yielded the product as a white solid (1.19 g) which was 72% pure by GC/MS analysis. A portion of this solid was further purified by recrystallization from methanol/water to yield white needles, mp 353.5 – 354 K. TLC: Rf = 0.54 in 7% ethyl acetate/petroleum ether. GC: Rt = 12.11 min. IR: 2952, 1718, 1589, 1269, 1095, 1008, 849, 753. MS: 412 (18), 410 (18), 397 (34), 395 (35), 355 (48), 353 (48), 327 (100), 325 (86), 185 (36), 183 (32), 69 (45), expected for C20H27BrO4 410.10. 13C NMR: 165.7, 131.7 (2), 131.3 (2), 128.7, 128.3, 113.1, 77.5, 65.9, 64.7, 48.3, 44.1, 33.5, 30.3, 24.1, 23.4, 23.2, 22.1, 18.1. 1H NMR: 7.92 (dt, J = 8.4, 1.8 Hz, 2H), 7.59 (dt, J = 9.0, 1.8 Hz, 2H), 4.53 (m, 1H), 4.48 (dd, J = 11.4, 4.2 Hz, 1H), 4.40 (dd, J = 11.4, 5.1 Hz, 1H), 4.09 (dd, J = 7.8, 6.9 Hz, 1H), 3.75 (dd, J = 7.8, 6.6 Hz, 1H), 2.24 (sept, J = 6.9 Hz, 1H)1.86 (ddd, J = 13.2, 2.4, 1.2 Hz, 1H), 1.71 - 1.77 (m, 1H), 1.56 - 1.68 (m, 2H), 1.34 - 1.46 (m, 2H), 1.01 (t, j = 12.9 Hz, 1H), 0.89 (d, J = 6.6 Hz, 3H), 0.87 (d, J = 7.2 Hz, 3H), 0.83 (d, J = 7.2 Hz, 3H), 0.86 - 0.90 (m, 1H).

Refinement top

Reflection 2 0 0 was obstructed by the beam stop and was omitted from the refinement. The structure shows pseudotranslation along the (0 1 1) diagonal. The p-bromo benzoate moieties do not obey the pseudotranslation and cause the doubling of the unit cell. The largest residual electron density peaks are located close to the bromine atoms, 0.84 Å from Br1 and 0.82 Å from Br2. The relatively large residual electron densities found (4.00 and 3.78 e Å-3) are associated with correlation effects due to the pseudotranslation exhibited by the structure. Q1, located close to Br1, is at a position that agrees with the position of Br2 translated along the direction of the pseudotranslation. Q2, on the other hand, reflects Br1 translated by half a unit cell along (0 1 1) (Fig. 5).

H atoms attached to carbon atoms were positioned geometrically and constrained to ride on their parent atoms, with C—H distances of 0.95 (CHar), 0.99 (CH2), 0.98 (CH3) or 1.00 Å (C—H) and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(Cmethyl) for methyl H.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid style view of the two molecules A and B of the title compound. Ellipsoid probability is at the 50% level.
[Figure 2] Fig. 2. Overlay of the two crystallographically independent molecules.
[Figure 3] Fig. 3. Packing view of the title compound, view down the (0 1 1) diagonal showing the pseudotranslation. Molecules A are shown in red, molecules B in blue.
[Figure 4] Fig. 4. Packing view of the title compound with intermolecular C—H···O interactions shown (blue dashed lines). Molecules A are shown in red, molecules B in blue.
[Figure 5] Fig. 5. Q-peaks (yellow spheres) caused by correlation effects due to pseudo-translation and their positions with respect to the Br atoms (green smaller spheres). Q1, located close to Br1, is created by translation of Br2 and Q2 by translation of Br1 by half a unit cell along the (0 1 1) direction. View is down the direction of the pseudotranslation as in Fig. 3.
[(2R,5R,6S,9R)-6-Isopropyl-9-methyl-1,4- dioxaspiro[4.5]decan-2-yl]methyl 4-bromobenzoate top
Crystal data top
C20H27BrO4F(000) = 1712
Mr = 411.33Dx = 1.420 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 3693 reflections
a = 42.976 (7) Åθ = 2.5–27.6°
b = 5.5763 (9) ŵ = 2.16 mm1
c = 16.072 (3) ÅT = 100 K
β = 92.618 (2)°Needle, colourless
V = 3847.5 (11) Å30.50 × 0.05 × 0.03 mm
Z = 8
Data collection top
Bruker SMART APEX CCD
diffractometer
9230 independent reflections
Radiation source: fine-focus sealed tube6765 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
ω scansθmax = 28.3°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 5756
Tmin = 0.588, Tmax = 0.746k = 77
17537 measured reflectionsl = 2121
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)] = 0.058H-atom parameters constrained
wR(F2) = 0.148 w = 1/[σ2(Fo2) + (0.0759P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
9230 reflectionsΔρmax = 4.00 e Å3
457 parametersΔρmin = 0.75 e Å3
1 restraintAbsolute structure: Flack (1983), 3965 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.000 (13)
Crystal data top
C20H27BrO4V = 3847.5 (11) Å3
Mr = 411.33Z = 8
Monoclinic, C2Mo Kα radiation
a = 42.976 (7) ŵ = 2.16 mm1
b = 5.5763 (9) ÅT = 100 K
c = 16.072 (3) Å0.50 × 0.05 × 0.03 mm
β = 92.618 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer
9230 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
6765 reflections with I > 2σ(I)
Tmin = 0.588, Tmax = 0.746Rint = 0.043
17537 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.148Δρmax = 4.00 e Å3
S = 1.02Δρmin = 0.75 e Å3
9230 reflectionsAbsolute structure: Flack (1983), 3965 Friedel pairs
457 parametersAbsolute structure parameter: 0.000 (13)
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
Br1A0.677987 (16)0.69491 (10)0.98525 (5)0.02577 (19)
Br1B0.822411 (16)0.57423 (10)0.51465 (5)0.02449 (18)
C1A0.79543 (14)0.4707 (12)0.7970 (4)0.0172 (14)
C2A0.76758 (14)0.5328 (11)0.8445 (4)0.0141 (12)
C3A0.74302 (14)0.3702 (11)0.8413 (4)0.0165 (13)
H3A0.74480.22690.80990.020*
C4A0.71634 (15)0.4125 (12)0.8826 (4)0.0167 (13)
H4A0.69980.29900.88140.020*
C5A0.71416 (17)0.6295 (9)0.9266 (5)0.0119 (18)
C6A0.73825 (16)0.7922 (11)0.9304 (4)0.0195 (14)
H6A0.73650.93600.96150.023*
C7A0.76521 (14)0.7446 (12)0.8881 (4)0.0188 (14)
H7A0.78180.85710.88940.023*
C8A0.84603 (15)0.6051 (12)0.7615 (5)0.0151 (15)
H8A10.85170.75960.73590.018*
H8A20.84190.48710.71630.018*
C9A0.87254 (10)0.5184 (8)0.8185 (3)0.0130 (9)
H9A0.87460.62230.86910.016*
C10A0.86975 (11)0.2539 (9)0.8437 (3)0.0169 (10)
H10A0.87860.22670.90090.020*
H10B0.84780.20050.84040.020*
C11A0.91262 (10)0.2894 (9)0.7673 (3)0.0139 (9)
C12A0.93969 (12)0.2590 (10)0.8319 (3)0.0172 (11)
H12A0.95570.38220.82210.021*
H12B0.93200.28520.88830.021*
C13A0.95462 (12)0.0102 (10)0.8282 (3)0.0201 (11)
H13A0.93880.11270.84230.024*
C14A0.96479 (11)0.0364 (10)0.7392 (3)0.0201 (11)
H14A0.98170.07640.72630.024*
H14B0.97310.20140.73570.024*
C15A0.93810 (12)0.0064 (10)0.6753 (3)0.0172 (11)
H15A0.92200.12890.68500.021*
H15B0.94580.03240.61890.021*
C16A0.92351 (11)0.2444 (9)0.6798 (3)0.0127 (10)
H16A0.94080.36080.67150.015*
C17A0.89885 (11)0.2924 (9)0.6090 (3)0.0151 (9)
H17A0.88560.42870.62700.018*
C18A0.87701 (16)0.0784 (15)0.5892 (5)0.0263 (15)
H18A0.86620.03370.63940.039*
H18B0.88930.05820.57070.039*
H18C0.86160.12370.54500.039*
C19A0.91434 (13)0.3708 (10)0.5304 (3)0.0234 (11)
H19A0.89830.40800.48690.035*
H19B0.92760.24110.51120.035*
H19C0.92710.51370.54220.035*
C20A0.98250 (12)0.0095 (12)0.8913 (3)0.0289 (13)
H20A0.99860.10520.87660.043*
H20B0.99100.17250.89020.043*
H20C0.97570.02650.94730.043*
C1B0.70385 (15)0.7839 (11)0.6994 (4)0.0161 (13)
C2B0.73214 (14)0.7265 (13)0.6536 (4)0.0182 (13)
C3B0.75673 (15)0.8902 (13)0.6586 (4)0.0199 (14)
H3B0.75501.03390.68980.024*
C4B0.78383 (15)0.8412 (12)0.6174 (4)0.0174 (14)
H4B0.80080.95060.62040.021*
C5B0.78569 (19)0.6330 (10)0.5726 (5)0.0149 (19)
C6B0.76197 (14)0.4659 (12)0.5682 (4)0.0163 (13)
H6B0.76410.32070.53810.020*
C7B0.73489 (14)0.5156 (11)0.6091 (4)0.0142 (13)
H7B0.71820.40420.60640.017*
C8B0.65383 (17)0.6320 (10)0.7341 (5)0.0187 (18)
H8B10.64960.80060.74930.022*
H8B20.65600.53580.78580.022*
C9B0.62768 (10)0.5353 (8)0.6779 (3)0.0136 (9)
H9B0.62550.63370.62590.016*
C10B0.63120 (11)0.2705 (9)0.6557 (3)0.0163 (10)
H10C0.62300.23790.59820.020*
H10D0.65330.21980.66110.020*
C11B0.58757 (10)0.3063 (9)0.7291 (3)0.0137 (9)
C12B0.56128 (12)0.2708 (10)0.6640 (3)0.0168 (10)
H12C0.56930.29560.60790.020*
H12D0.54490.39190.67240.020*
C13B0.54689 (11)0.0148 (10)0.6691 (3)0.0157 (11)
H13B0.56310.10540.65510.019*
C14B0.53697 (11)0.0327 (9)0.7582 (3)0.0175 (10)
H14C0.51920.07260.77010.021*
H14D0.52990.20100.76250.021*
C15B0.56317 (12)0.0115 (10)0.8228 (3)0.0153 (11)
H15C0.58000.10630.81490.018*
H15D0.55530.01330.87910.018*
C16B0.57645 (11)0.2651 (9)0.8171 (3)0.0124 (10)
H16B0.55840.37600.82310.015*
C17B0.60009 (12)0.3292 (9)0.8881 (3)0.0180 (10)
H17B0.61170.47490.87070.022*
C18B0.6239 (2)0.1343 (11)0.9093 (5)0.028 (2)
H18D0.61320.00960.92820.042*
H18E0.63850.19130.95370.042*
H18F0.63540.09590.85980.042*
C19B0.58304 (13)0.3940 (11)0.9663 (3)0.0257 (12)
H19D0.59830.43111.01170.039*
H19E0.57010.25830.98240.039*
H19F0.56980.53420.95500.039*
C20B0.51938 (12)0.0086 (11)0.6060 (3)0.0262 (12)
H20D0.50320.10690.61950.039*
H20E0.51090.17160.60820.039*
H20F0.52640.02370.55000.039*
O1A0.79755 (11)0.2908 (9)0.7548 (3)0.0252 (11)
O2A0.81834 (12)0.6356 (6)0.8087 (3)0.0151 (13)
O3A0.90037 (7)0.5265 (6)0.7737 (2)0.0152 (7)
O4A0.88748 (12)0.1333 (6)0.7838 (3)0.0165 (13)
O1B0.70079 (11)0.9560 (8)0.7431 (3)0.0222 (10)
O2B0.68186 (12)0.6166 (8)0.6883 (4)0.0186 (13)
O3B0.59946 (7)0.5436 (6)0.7213 (2)0.0158 (7)
O4B0.61311 (12)0.1522 (7)0.7151 (3)0.0132 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0183 (4)0.0367 (4)0.0226 (4)0.0055 (4)0.0042 (3)0.0042 (4)
Br1B0.0170 (4)0.0360 (4)0.0207 (4)0.0008 (4)0.0030 (3)0.0012 (4)
C1A0.013 (3)0.023 (3)0.015 (3)0.002 (2)0.000 (2)0.004 (3)
C2A0.022 (3)0.009 (3)0.012 (3)0.003 (2)0.001 (2)0.002 (3)
C3A0.021 (3)0.008 (3)0.020 (3)0.001 (2)0.001 (3)0.001 (2)
C4A0.020 (3)0.013 (3)0.017 (3)0.005 (2)0.002 (3)0.002 (3)
C5A0.009 (4)0.017 (4)0.009 (4)0.0005 (19)0.000 (3)0.005 (2)
C6A0.034 (4)0.004 (3)0.020 (3)0.001 (3)0.002 (3)0.000 (2)
C7A0.015 (3)0.015 (4)0.026 (4)0.001 (3)0.001 (3)0.006 (3)
C8A0.015 (3)0.017 (3)0.014 (3)0.001 (2)0.005 (3)0.002 (2)
C9A0.015 (2)0.014 (2)0.010 (2)0.0014 (17)0.0048 (17)0.0005 (18)
C10A0.017 (2)0.017 (3)0.016 (2)0.0037 (18)0.0025 (18)0.0067 (19)
C11A0.011 (2)0.016 (2)0.015 (2)0.0002 (18)0.0002 (17)0.0033 (19)
C12A0.011 (2)0.024 (3)0.016 (2)0.002 (2)0.002 (2)0.002 (2)
C13A0.015 (2)0.031 (3)0.014 (2)0.006 (2)0.008 (2)0.007 (2)
C14A0.014 (2)0.029 (3)0.018 (2)0.009 (2)0.0013 (19)0.004 (2)
C15A0.019 (3)0.021 (3)0.012 (2)0.001 (2)0.001 (2)0.004 (2)
C16A0.012 (2)0.015 (3)0.011 (2)0.002 (2)0.0002 (19)0.0048 (18)
C17A0.018 (2)0.015 (2)0.012 (2)0.0008 (19)0.0034 (18)0.0032 (19)
C18A0.029 (4)0.027 (3)0.021 (3)0.010 (3)0.014 (3)0.010 (3)
C19A0.034 (3)0.023 (3)0.013 (2)0.003 (2)0.002 (2)0.006 (2)
C20A0.021 (3)0.052 (4)0.013 (2)0.005 (3)0.001 (2)0.006 (2)
C1B0.025 (3)0.008 (3)0.014 (3)0.005 (2)0.003 (3)0.000 (2)
C2B0.018 (3)0.018 (4)0.018 (3)0.001 (3)0.002 (3)0.005 (3)
C3B0.029 (4)0.021 (3)0.009 (3)0.000 (3)0.002 (3)0.004 (3)
C4B0.018 (3)0.020 (3)0.014 (3)0.001 (2)0.001 (3)0.009 (3)
C5B0.019 (4)0.015 (4)0.012 (4)0.005 (2)0.005 (4)0.003 (2)
C6B0.013 (3)0.024 (3)0.011 (3)0.000 (2)0.003 (2)0.003 (3)
C7B0.026 (3)0.007 (3)0.009 (3)0.004 (2)0.006 (2)0.000 (2)
C8B0.018 (4)0.020 (4)0.018 (4)0.001 (2)0.003 (3)0.002 (2)
C9B0.015 (2)0.014 (3)0.012 (2)0.0012 (17)0.0026 (17)0.0013 (18)
C10B0.017 (2)0.017 (2)0.015 (2)0.0012 (19)0.0045 (18)0.0056 (19)
C11B0.010 (2)0.012 (2)0.019 (2)0.0002 (17)0.0004 (17)0.0055 (19)
C12B0.015 (2)0.021 (3)0.015 (2)0.002 (2)0.003 (2)0.001 (2)
C13B0.011 (2)0.020 (3)0.017 (2)0.001 (2)0.002 (2)0.002 (2)
C14B0.016 (2)0.018 (3)0.018 (2)0.0035 (18)0.0007 (19)0.003 (2)
C15B0.015 (2)0.017 (3)0.014 (2)0.000 (2)0.005 (2)0.0024 (19)
C16B0.011 (2)0.015 (2)0.011 (2)0.003 (2)0.0034 (18)0.0021 (18)
C17B0.025 (3)0.017 (2)0.012 (2)0.001 (2)0.0023 (19)0.0071 (19)
C18B0.034 (4)0.029 (4)0.020 (4)0.004 (2)0.007 (3)0.006 (2)
C19B0.032 (3)0.032 (3)0.013 (2)0.001 (2)0.001 (2)0.009 (2)
C20B0.020 (3)0.039 (3)0.019 (3)0.005 (2)0.001 (2)0.009 (2)
O1A0.026 (2)0.022 (2)0.028 (3)0.006 (2)0.008 (2)0.011 (2)
O2A0.017 (3)0.012 (3)0.016 (3)0.0001 (14)0.003 (2)0.0024 (14)
O3A0.0153 (16)0.0121 (18)0.0187 (17)0.0002 (12)0.0058 (13)0.0006 (14)
O4A0.017 (3)0.011 (3)0.022 (3)0.0002 (14)0.006 (2)0.0029 (15)
O1B0.025 (2)0.020 (2)0.022 (2)0.0031 (18)0.0022 (19)0.008 (2)
O2B0.013 (3)0.018 (3)0.025 (3)0.0051 (15)0.004 (2)0.0064 (17)
O3B0.0175 (16)0.0105 (18)0.0198 (17)0.0008 (13)0.0047 (13)0.0000 (14)
O4B0.016 (3)0.008 (2)0.016 (3)0.0006 (14)0.002 (2)0.0016 (15)
Geometric parameters (Å, º) top
Br1A—C5A1.889 (7)C20A—H20C0.9800
Br1B—C5B1.897 (8)C1B—O1B1.199 (8)
C1A—O1A1.217 (8)C1B—O2B1.334 (7)
C1A—O2A1.354 (8)C1B—C2B1.485 (9)
C1A—C2A1.489 (8)C2B—C7B1.385 (10)
C2A—C7A1.380 (10)C2B—C3B1.396 (9)
C2A—C3A1.391 (9)C3B—C4B1.393 (9)
C3A—C4A1.371 (9)C3B—H3B0.9500
C3A—H3A0.9500C4B—C5B1.370 (9)
C4A—C5A1.408 (9)C4B—H4B0.9500
C4A—H4A0.9500C5B—C6B1.381 (9)
C5A—C6A1.376 (9)C6B—C7B1.390 (8)
C6A—C7A1.395 (9)C6B—H6B0.9500
C6A—H6A0.9500C7B—H7B0.9500
C7A—H7A0.9500C8B—O2B1.443 (9)
C8A—O2A1.450 (8)C8B—C9B1.509 (8)
C8A—C9A1.508 (8)C8B—H8B10.9900
C8A—H8A10.9900C8B—H8B20.9900
C8A—H8A20.9900C9B—O3B1.427 (5)
C9A—O3A1.424 (5)C9B—C10B1.528 (6)
C9A—C10A1.536 (6)C9B—H9B1.0000
C9A—H9A1.0000C10B—O4B1.421 (6)
C10A—O4A1.423 (7)C10B—H10C0.9900
C10A—H10A0.9900C10B—H10D0.9900
C10A—H10B0.9900C11B—O4B1.420 (6)
C11A—O4A1.422 (6)C11B—O3B1.426 (6)
C11A—O3A1.429 (6)C11B—C12B1.517 (7)
C11A—C16A1.524 (6)C11B—C16B1.530 (6)
C11A—C12A1.533 (7)C12B—C13B1.559 (8)
C12A—C13A1.531 (8)C12B—H12C0.9900
C12A—H12A0.9900C12B—H12D0.9900
C12A—H12B0.9900C13B—C20B1.527 (7)
C13A—C20A1.537 (7)C13B—C14B1.536 (7)
C13A—C14A1.538 (7)C13B—H13B1.0000
C13A—H13A1.0000C14B—C15B1.517 (7)
C14A—C15A1.513 (7)C14B—H14C0.9900
C14A—H14A0.9900C14B—H14D0.9900
C14A—H14B0.9900C15B—C16B1.529 (8)
C15A—C16A1.535 (7)C15B—H15C0.9900
C15A—H15A0.9900C15B—H15D0.9900
C15A—H15B0.9900C16B—C17B1.535 (7)
C16A—C17A1.542 (7)C16B—H16B1.0000
C16A—H16A1.0000C17B—C18B1.522 (9)
C17A—C19A1.520 (6)C17B—C19B1.527 (7)
C17A—C18A1.543 (9)C17B—H17B1.0000
C17A—H17A1.0000C18B—H18D0.9800
C18A—H18A0.9800C18B—H18E0.9800
C18A—H18B0.9800C18B—H18F0.9800
C18A—H18C0.9800C19B—H19D0.9800
C19A—H19A0.9800C19B—H19E0.9800
C19A—H19B0.9800C19B—H19F0.9800
C19A—H19C0.9800C20B—H20D0.9800
C20A—H20A0.9800C20B—H20E0.9800
C20A—H20B0.9800C20B—H20F0.9800
O1A—C1A—O2A124.4 (6)C7B—C2B—C3B120.2 (6)
O1A—C1A—C2A124.0 (6)C7B—C2B—C1B122.1 (6)
O2A—C1A—C2A111.6 (6)C3B—C2B—C1B117.7 (6)
C7A—C2A—C3A120.2 (6)C4B—C3B—C2B119.5 (7)
C7A—C2A—C1A122.6 (6)C4B—C3B—H3B120.3
C3A—C2A—C1A117.1 (6)C2B—C3B—H3B120.3
C4A—C3A—C2A121.3 (6)C5B—C4B—C3B119.1 (7)
C4A—C3A—H3A119.3C5B—C4B—H4B120.5
C2A—C3A—H3A119.3C3B—C4B—H4B120.5
C3A—C4A—C5A117.9 (6)C4B—C5B—C6B122.6 (7)
C3A—C4A—H4A121.0C4B—C5B—Br1B118.3 (6)
C5A—C4A—H4A121.0C6B—C5B—Br1B119.1 (5)
C6A—C5A—C4A121.4 (7)C5B—C6B—C7B118.2 (6)
C6A—C5A—Br1A119.1 (5)C5B—C6B—H6B120.9
C4A—C5A—Br1A119.5 (5)C7B—C6B—H6B120.9
C5A—C6A—C7A119.6 (6)C2B—C7B—C6B120.5 (6)
C5A—C6A—H6A120.2C2B—C7B—H7B119.8
C7A—C6A—H6A120.2C6B—C7B—H7B119.8
C2A—C7A—C6A119.5 (6)O2B—C8B—C9B106.8 (6)
C2A—C7A—H7A120.3O2B—C8B—H8B1110.4
C6A—C7A—H7A120.3C9B—C8B—H8B1110.4
O2A—C8A—C9A109.6 (6)O2B—C8B—H8B2110.4
O2A—C8A—H8A1109.8C9B—C8B—H8B2110.4
C9A—C8A—H8A1109.8H8B1—C8B—H8B2108.6
O2A—C8A—H8A2109.8O3B—C9B—C8B108.8 (4)
C9A—C8A—H8A2109.8O3B—C9B—C10B103.9 (4)
H8A1—C8A—H8A2108.2C8B—C9B—C10B113.9 (4)
O3A—C9A—C8A108.2 (4)O3B—C9B—H9B110.0
O3A—C9A—C10A104.0 (4)C8B—C9B—H9B110.0
C8A—C9A—C10A113.7 (4)C10B—C9B—H9B110.0
O3A—C9A—H9A110.3O4B—C10B—C9B103.2 (4)
C8A—C9A—H9A110.3O4B—C10B—H10C111.1
C10A—C9A—H9A110.3C9B—C10B—H10C111.1
O4A—C10A—C9A103.0 (4)O4B—C10B—H10D111.1
O4A—C10A—H10A111.2C9B—C10B—H10D111.1
C9A—C10A—H10A111.2H10C—C10B—H10D109.1
O4A—C10A—H10B111.2O4B—C11B—O3B105.4 (4)
C9A—C10A—H10B111.2O4B—C11B—C12B111.7 (4)
H10A—C10A—H10B109.1O3B—C11B—C12B108.6 (4)
O4A—C11A—O3A105.5 (3)O4B—C11B—C16B109.4 (4)
O4A—C11A—C16A109.9 (4)O3B—C11B—C16B110.4 (4)
O3A—C11A—C16A110.4 (4)C12B—C11B—C16B111.3 (4)
O4A—C11A—C12A111.5 (4)C11B—C12B—C13B111.6 (4)
O3A—C11A—C12A108.9 (4)C11B—C12B—H12C109.3
C16A—C11A—C12A110.6 (4)C13B—C12B—H12C109.3
C13A—C12A—C11A112.4 (4)C11B—C12B—H12D109.3
C13A—C12A—H12A109.1C13B—C12B—H12D109.3
C11A—C12A—H12A109.1H12C—C12B—H12D108.0
C13A—C12A—H12B109.1C20B—C13B—C14B111.4 (4)
C11A—C12A—H12B109.1C20B—C13B—C12B109.9 (4)
H12A—C12A—H12B107.9C14B—C13B—C12B109.5 (4)
C12A—C13A—C20A110.8 (5)C20B—C13B—H13B108.7
C12A—C13A—C14A109.0 (4)C14B—C13B—H13B108.7
C20A—C13A—C14A110.8 (4)C12B—C13B—H13B108.7
C12A—C13A—H13A108.7C15B—C14B—C13B112.4 (4)
C20A—C13A—H13A108.7C15B—C14B—H14C109.1
C14A—C13A—H13A108.7C13B—C14B—H14C109.1
C15A—C14A—C13A112.0 (4)C15B—C14B—H14D109.1
C15A—C14A—H14A109.2C13B—C14B—H14D109.1
C13A—C14A—H14A109.2H14C—C14B—H14D107.9
C15A—C14A—H14B109.2C14B—C15B—C16B112.1 (4)
C13A—C14A—H14B109.2C14B—C15B—H15C109.2
H14A—C14A—H14B107.9C16B—C15B—H15C109.2
C14A—C15A—C16A111.5 (4)C14B—C15B—H15D109.2
C14A—C15A—H15A109.3C16B—C15B—H15D109.2
C16A—C15A—H15A109.3H15C—C15B—H15D107.9
C14A—C15A—H15B109.3C15B—C16B—C11B109.2 (4)
C16A—C15A—H15B109.3C15B—C16B—C17B114.0 (4)
H15A—C15A—H15B108.0C11B—C16B—C17B115.3 (4)
C11A—C16A—C15A109.7 (4)C15B—C16B—H16B105.8
C11A—C16A—C17A115.0 (4)C11B—C16B—H16B105.8
C15A—C16A—C17A113.1 (4)C17B—C16B—H16B105.8
C11A—C16A—H16A106.1C18B—C17B—C19B109.1 (5)
C15A—C16A—H16A106.1C18B—C17B—C16B114.6 (5)
C17A—C16A—H16A106.1C19B—C17B—C16B110.0 (4)
C19A—C17A—C16A110.6 (4)C18B—C17B—H17B107.6
C19A—C17A—C18A109.7 (5)C19B—C17B—H17B107.6
C16A—C17A—C18A114.1 (5)C16B—C17B—H17B107.6
C19A—C17A—H17A107.4C17B—C18B—H18D109.5
C16A—C17A—H17A107.4C17B—C18B—H18E109.5
C18A—C17A—H17A107.4H18D—C18B—H18E109.5
C17A—C18A—H18A109.5C17B—C18B—H18F109.5
C17A—C18A—H18B109.5H18D—C18B—H18F109.5
H18A—C18A—H18B109.5H18E—C18B—H18F109.5
C17A—C18A—H18C109.5C17B—C19B—H19D109.5
H18A—C18A—H18C109.5C17B—C19B—H19E109.5
H18B—C18A—H18C109.5H19D—C19B—H19E109.5
C17A—C19A—H19A109.5C17B—C19B—H19F109.5
C17A—C19A—H19B109.5H19D—C19B—H19F109.5
H19A—C19A—H19B109.5H19E—C19B—H19F109.5
C17A—C19A—H19C109.5C13B—C20B—H20D109.5
H19A—C19A—H19C109.5C13B—C20B—H20E109.5
H19B—C19A—H19C109.5H20D—C20B—H20E109.5
C13A—C20A—H20A109.5C13B—C20B—H20F109.5
C13A—C20A—H20B109.5H20D—C20B—H20F109.5
H20A—C20A—H20B109.5H20E—C20B—H20F109.5
C13A—C20A—H20C109.5C1A—O2A—C8A117.1 (5)
H20A—C20A—H20C109.5C9A—O3A—C11A109.1 (3)
H20B—C20A—H20C109.5C11A—O4A—C10A105.8 (4)
O1B—C1B—O2B122.8 (6)C1B—O2B—C8B119.5 (5)
O1B—C1B—C2B125.2 (6)C11B—O3B—C9B109.2 (3)
O2B—C1B—C2B111.9 (6)C11B—O4B—C10B106.0 (4)
O1A—C1A—C2A—C7A176.4 (7)C1B—C2B—C7B—C6B178.8 (6)
O2A—C1A—C2A—C7A5.4 (9)C5B—C6B—C7B—C2B0.7 (10)
O1A—C1A—C2A—C3A1.6 (10)O2B—C8B—C9B—O3B179.1 (4)
O2A—C1A—C2A—C3A176.6 (6)O2B—C8B—C9B—C10B63.7 (6)
C7A—C2A—C3A—C4A1.5 (10)O3B—C9B—C10B—O4B22.7 (5)
C1A—C2A—C3A—C4A179.6 (6)C8B—C9B—C10B—O4B95.5 (5)
C2A—C3A—C4A—C5A1.7 (10)O4B—C11B—C12B—C13B64.6 (5)
C3A—C4A—C5A—C6A1.7 (10)O3B—C11B—C12B—C13B179.6 (4)
C3A—C4A—C5A—Br1A179.5 (5)C16B—C11B—C12B—C13B57.9 (5)
C4A—C5A—C6A—C7A1.5 (10)C11B—C12B—C13B—C20B176.8 (4)
Br1A—C5A—C6A—C7A179.3 (5)C11B—C12B—C13B—C14B54.1 (6)
C3A—C2A—C7A—C6A1.3 (10)C20B—C13B—C14B—C15B174.8 (4)
C1A—C2A—C7A—C6A179.2 (6)C12B—C13B—C14B—C15B53.0 (6)
C5A—C6A—C7A—C2A1.2 (10)C13B—C14B—C15B—C16B55.9 (6)
O2A—C8A—C9A—O3A170.9 (4)C14B—C15B—C16B—C11B56.9 (5)
O2A—C8A—C9A—C10A74.2 (6)C14B—C15B—C16B—C17B172.5 (4)
O3A—C9A—C10A—O4A23.3 (5)O4B—C11B—C16B—C15B65.8 (5)
C8A—C9A—C10A—O4A94.1 (5)O3B—C11B—C16B—C15B178.7 (4)
O4A—C11A—C12A—C13A65.0 (5)C12B—C11B—C16B—C15B58.0 (5)
O3A—C11A—C12A—C13A179.0 (4)O4B—C11B—C16B—C17B64.0 (5)
C16A—C11A—C12A—C13A57.5 (6)O3B—C11B—C16B—C17B51.5 (5)
C11A—C12A—C13A—C20A177.6 (4)C12B—C11B—C16B—C17B172.1 (4)
C11A—C12A—C13A—C14A55.4 (6)C15B—C16B—C17B—C18B44.4 (7)
C12A—C13A—C14A—C15A55.0 (6)C11B—C16B—C17B—C18B83.1 (6)
C20A—C13A—C14A—C15A177.2 (5)C15B—C16B—C17B—C19B79.0 (5)
C13A—C14A—C15A—C16A57.1 (6)C11B—C16B—C17B—C19B153.6 (4)
O4A—C11A—C16A—C15A66.9 (5)O1A—C1A—O2A—C8A5.8 (10)
O3A—C11A—C16A—C15A177.2 (4)C2A—C1A—O2A—C8A176.0 (5)
C12A—C11A—C16A—C15A56.5 (5)C9A—C8A—O2A—C1A106.5 (6)
O4A—C11A—C16A—C17A61.9 (5)C8A—C9A—O3A—C11A118.0 (4)
O3A—C11A—C16A—C17A54.1 (5)C10A—C9A—O3A—C11A3.2 (5)
C12A—C11A—C16A—C17A174.7 (4)O4A—C11A—O3A—C9A18.3 (5)
C14A—C15A—C16A—C11A57.0 (5)C16A—C11A—O3A—C9A137.0 (4)
C14A—C15A—C16A—C17A173.2 (4)C12A—C11A—O3A—C9A101.4 (4)
C11A—C16A—C17A—C19A150.3 (4)O3A—C11A—O4A—C10A34.0 (5)
C15A—C16A—C17A—C19A82.6 (5)C16A—C11A—O4A—C10A153.0 (4)
C11A—C16A—C17A—C18A85.5 (6)C12A—C11A—O4A—C10A84.2 (5)
C15A—C16A—C17A—C18A41.6 (6)C9A—C10A—O4A—C11A35.1 (5)
O1B—C1B—C2B—C7B175.2 (7)O1B—C1B—O2B—C8B4.0 (10)
O2B—C1B—C2B—C7B3.2 (9)C2B—C1B—O2B—C8B174.5 (6)
O1B—C1B—C2B—C3B2.9 (10)C9B—C8B—O2B—C1B146.1 (6)
O2B—C1B—C2B—C3B178.7 (6)O4B—C11B—O3B—C9B18.4 (5)
C7B—C2B—C3B—C4B1.0 (10)C12B—C11B—O3B—C9B101.4 (4)
C1B—C2B—C3B—C4B179.1 (6)C16B—C11B—O3B—C9B136.4 (4)
C2B—C3B—C4B—C5B0.2 (10)C8B—C9B—O3B—C11B119.0 (4)
C3B—C4B—C5B—C6B1.7 (10)C10B—C9B—O3B—C11B2.8 (5)
C3B—C4B—C5B—Br1B178.4 (5)O3B—C11B—O4B—C10B33.6 (5)
C4B—C5B—C6B—C7B1.9 (10)C12B—C11B—O4B—C10B84.1 (5)
Br1B—C5B—C6B—C7B178.1 (5)C16B—C11B—O4B—C10B152.3 (4)
C3B—C2B—C7B—C6B0.7 (10)C9B—C10B—O4B—C11B34.6 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3A—H3A···O1Bi0.952.613.295 (8)129
C13B—H13B···O3Bi1.002.693.541 (6)143
C15B—H15C···O3Bi0.992.623.484 (6)145
C8A—H8A1···O4Aii0.992.683.452 (8)135
C15A—H15A···O3Ai0.992.593.486 (6)150
C3B—H3B···O1Aii0.952.513.195 (8)129
C8B—H8B1···O4Bii0.992.563.394 (8)143
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC20H27BrO4
Mr411.33
Crystal system, space groupMonoclinic, C2
Temperature (K)100
a, b, c (Å)42.976 (7), 5.5763 (9), 16.072 (3)
β (°) 92.618 (2)
V3)3847.5 (11)
Z8
Radiation typeMo Kα
µ (mm1)2.16
Crystal size (mm)0.50 × 0.05 × 0.03
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.588, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
17537, 9230, 6765
Rint0.043
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.148, 1.02
No. of reflections9230
No. of parameters457
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)4.00, 0.75
Absolute structureFlack (1983), 3965 Friedel pairs
Absolute structure parameter0.000 (13)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3A—H3A···O1Bi0.952.613.295 (8)129.2
C13B—H13B···O3Bi1.002.693.541 (6)142.8
C15B—H15C···O3Bi0.992.623.484 (6)145.2
C8A—H8A1···O4Aii0.992.683.452 (8)134.9
C15A—H15A···O3Ai0.992.593.486 (6)150.4
C3B—H3B···O1Aii0.952.513.195 (8)128.8
C8B—H8B1···O4Bii0.992.563.394 (8)142.5
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
 

Acknowledgements

The diffractometer was funded by NSF grant 0087210, Ohio Board of Regents grant CAP-491 and YSU.

References

First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationGreenberg, M. (1999). US Patent No. 5 977 166, Nov. 2.  Google Scholar
First citationKiessling, A., Campana, C. & Kastner, M. E. (2009a). Acta Cryst. E65, o1540.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKiessling, A., Ganong, C. & Johnson, A. (2009b). Am. J. Undergrad. Res. 8, 1–6.  Google Scholar
First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 3| March 2011| Pages o733-o734
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