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The crystal structures of Emycin E (1), di-o-bromobenzoyl-Emycin F (2) and o-bromobenzoyl-Emycin D (3) have been determined by X-ray analysis at low temperature. Emycin E and o-bromobenzoyl-Emycin D both crystallize with two molecules in a triclinic unit cell. These two structures can be solved and refined either in the centrosymmetric space group P\bar 1, with apparent disorder localized at or around the expected chiral centre, or in the non-centrosymmetric space group P1 as mixtures of two diastereomers without disorder. Only the latter interpretation is consistent with the chemical and spectroscopic evidence. Refinements in the centrosymmetric and non-centrosymmetric space groups are compared in this paper and are shown to favour the chemically correct interpretation, more decisively so in the case of the bromo derivative as a result of the anomalous dispersion of bromine. Structures (1) and (3) provide a dramatic warning of the dangers inherent in the conventional wisdom that if a structure can be refined satisfactorarily in both centrosymmetric and non-centrosymmetric space groups, the former should always be chosen. In these two cases, despite apparently acceptable intensity statistics and R factors (5.87 and 3.55%), the choice of the centrosymmetric space group leads to the serious chemical error that the triclinic unit cell contains a racemate rather than two chiral diastereomers! The weakest reflections are shown to be most sensitive to the correct choice of space group, underlining the importance of refining against all data rather than against intensities greater than a specified threshold. The use of similar-distance restraints is shown to be beneficial in both P1 refinements. Di-o-bromobenzoyl-Emycin F crystallizes in the monoclinic space group P21 with one molecule in the asymmetric unit and so does not give rise to these problems of interpretation. The absolute configuration of the two bromo derivatives, and hence the Emycins in general, was determined unambiguously as S at the chiral centre C3.

Supporting information

cif

Crystallographic Information File (CIF)
Contains datablocks ende3, gelb, salbei

CCDC references: 134776; 134777; 134778

Computing details top

For all compounds, data collection: DIF4 (Stoe & Cie, 1988a); cell refinement: DIF4 (Stoe & Cie, 1988a); data reduction: REDU4 (Stoe & Cie, 1988b); program(s) used to solve structure: SHELXS90 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL 5.1 (Sheldrick, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
(ende3) top
Crystal data top
C19H18O4Z = 2
Mr = 310.33F(000) = 328
Triclinic, P1Dx = 1.372 Mg m3
a = 8.075 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.871 (2) ÅCell parameters from 50 reflections
c = 11.606 (2) Åθ = 10–12.5°
α = 72.69 (3)°µ = 0.10 mm1
β = 80.07 (3)°T = 153 K
γ = 71.84 (3)°Blocks, colourless
V = 751.3 (3) Å30.4 × 0.2 × 0.2 mm
Data collection top
Stoe-Siemens-Huber AED2 four-circle
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 3.1°
Graphite monochromatorh = 99
profile data from 2θ/ω scansk = 1010
5336 measured reflectionsl = 1313
5336 independent reflections3 standard reflections every 90 min
4018 reflections with I > 2σ(I)
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 atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.030P)2 + 0.8P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5336 reflectionsΔρmax = 0.19 e Å3
421 parametersΔρmin = 0.22 e Å3
68 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 3 (2)
Crystal data top
C19H18O4γ = 71.84 (3)°
Mr = 310.33V = 751.3 (3) Å3
Triclinic, P1Z = 2
a = 8.075 (2) ÅMo Kα radiation
b = 8.871 (2) ŵ = 0.10 mm1
c = 11.606 (2) ÅT = 153 K
α = 72.69 (3)°0.4 × 0.2 × 0.2 mm
β = 80.07 (3)°
Data collection top
Stoe-Siemens-Huber AED2 four-circle
diffractometer
4018 reflections with I > 2σ(I)
5336 measured reflectionsRint = 0.000
5336 independent reflections3 standard reflections every 90 min
Refinement top
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118Δρmax = 0.19 e Å3
S = 1.03Δρmin = 0.22 e Å3
5336 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
421 parametersAbsolute structure parameter: 3 (2)
68 restraints
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
O11.2807 (5)0.4671 (5)0.0429 (4)0.0295 (11)
C11.4036 (7)0.4809 (6)0.0336 (5)0.0201 (14)
C21.5307 (8)0.3314 (7)0.0646 (6)0.0276 (16)
H2A1.47070.28680.10880.033*
H2B1.56360.24690.01180.033*
C31.6965 (7)0.3589 (6)0.1404 (5)0.0241 (14)
H31.76670.38760.09130.029*
C41.6411 (8)0.5043 (6)0.2485 (5)0.0252 (15)
H4A1.74640.52640.30020.030*
H4B1.57080.47720.29740.030*
C4A1.5353 (7)0.6555 (6)0.2088 (5)0.0205 (14)
C51.5472 (8)0.8096 (7)0.2795 (5)0.0249 (15)
H51.61960.81800.35360.030*
C61.4557 (8)0.9505 (7)0.2437 (5)0.0268 (16)
H61.46471.05470.29340.032*
C6A1.3507 (7)0.9398 (6)0.1355 (5)0.0224 (14)
O6A1.2669 (6)1.0860 (5)0.1085 (4)0.0302 (11)
H6A1.23551.06910.03400.045*
O71.2253 (5)0.9084 (5)0.1095 (4)0.0230 (10)
C71.0646 (7)0.9451 (7)0.1866 (5)0.0234 (15)
H7A1.02731.06230.18710.028*
H7B1.07910.87630.27070.028*
C7A0.9356 (6)0.9053 (7)0.1304 (5)0.0198 (14)
C80.7563 (7)0.9394 (7)0.1510 (5)0.0224 (14)
O80.6749 (5)1.0339 (5)0.2297 (4)0.0271 (11)
H80.58731.00350.26730.041*
C90.6665 (7)0.8842 (7)0.0879 (5)0.0233 (14)
H90.54240.91030.09900.028*
C100.7589 (7)0.7904 (7)0.0081 (5)0.0233 (15)
H100.69620.75340.03500.028*
C110.9392 (7)0.7496 (7)0.0099 (5)0.0207 (14)
H111.00140.68270.06250.025*
C11A1.0262 (7)0.8097 (6)0.0515 (5)0.0194 (14)
C121.2195 (7)0.7798 (6)0.0567 (5)0.0220 (14)
H121.26560.67020.11400.026*
C12A1.3320 (7)0.7887 (6)0.0617 (5)0.0179 (13)
C12B1.4251 (7)0.6461 (6)0.1007 (5)0.0197 (14)
C131.8066 (6)0.2064 (5)0.1797 (4)0.0375 (10)
H13A1.84260.11610.10790.056*
H13B1.91070.22940.23060.056*
H13C1.73770.17520.22580.056*
O1'0.4082 (5)0.9157 (5)0.3601 (4)0.0307 (12)
C1'0.2874 (7)0.9032 (6)0.4390 (5)0.0227 (15)
C2'0.1687 (8)1.0571 (7)0.4683 (6)0.0289 (15)
H2'10.13621.14010.39120.035*
H2'20.23551.10010.50890.035*
C3'0.0010 (8)1.0407 (7)0.5484 (5)0.0290 (15)
H3'0.04731.13940.58150.035*
C4'0.0481 (8)0.8894 (6)0.6540 (5)0.0294 (16)
H4'10.11970.90950.70610.035*
H4'20.06070.87220.70320.035*
C4A'0.1476 (7)0.7354 (6)0.6153 (5)0.0232 (14)
C5'0.1312 (8)0.5834 (6)0.6852 (5)0.0254 (15)
H5'0.05460.57790.75730.030*
C6'0.2213 (7)0.4417 (7)0.6538 (5)0.0241 (15)
H6'0.20950.33920.70510.029*
C6A'0.3311 (7)0.4465 (6)0.5467 (5)0.0230 (15)
O6A'0.4175 (6)0.2993 (5)0.5210 (4)0.0312 (11)
H6A'0.46160.31610.44880.047*
O7'0.4586 (5)0.4714 (5)0.3001 (4)0.0248 (11)
C7'0.6191 (7)0.4354 (8)0.2212 (5)0.0235 (15)
H7'10.60340.50420.13710.028*
H7'20.65770.31810.22080.028*
C7A'0.7461 (6)0.4774 (7)0.2773 (5)0.0194 (14)
C8'0.9270 (7)0.4403 (7)0.2552 (5)0.0210 (14)
O8'1.0052 (5)0.3514 (5)0.1721 (4)0.0297 (11)
H8'1.10520.36450.14770.045*
C9'1.0184 (8)0.4946 (7)0.3180 (6)0.0271 (16)
H9'1.14210.47090.30410.033*
C10'0.9298 (7)0.5836 (8)0.4010 (6)0.0268 (15)
H10'0.99360.61820.44500.032*
C11'0.7483 (7)0.6224 (7)0.4203 (5)0.0230 (14)
H11'0.68710.68430.47640.028*
C1A'0.6598 (6)0.5693 (7)0.3566 (5)0.0182 (14)
C12'0.4650 (6)0.6015 (6)0.3522 (5)0.0184 (13)
H12'0.42000.71060.29410.022*
C2A'0.3508 (7)0.5956 (6)0.4709 (5)0.0211 (14)
C2B'0.2613 (7)0.7408 (6)0.5084 (5)0.0193 (13)
C13'0.1375 (5)1.0327 (5)0.4774 (4)0.0336 (10)
H13D0.24771.03640.52890.050*
H13E0.09800.93020.45220.050*
H13F0.15561.12640.40560.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.023 (2)0.027 (2)0.037 (3)0.012 (2)0.007 (2)0.007 (2)
C10.016 (3)0.025 (3)0.019 (3)0.006 (3)0.004 (3)0.003 (3)
C20.035 (4)0.015 (3)0.027 (3)0.004 (3)0.004 (3)0.005 (2)
C30.025 (3)0.024 (3)0.022 (3)0.005 (2)0.005 (2)0.010 (2)
C40.029 (4)0.023 (3)0.020 (3)0.008 (3)0.001 (3)0.001 (2)
C4A0.017 (3)0.025 (3)0.019 (3)0.006 (3)0.002 (3)0.005 (3)
C50.027 (4)0.032 (4)0.018 (3)0.015 (3)0.005 (3)0.006 (3)
C60.025 (3)0.021 (3)0.032 (4)0.008 (3)0.001 (3)0.003 (3)
C6A0.018 (3)0.020 (3)0.029 (4)0.004 (3)0.007 (3)0.006 (3)
O6A0.031 (3)0.023 (2)0.032 (3)0.0052 (19)0.003 (2)0.003 (2)
O70.025 (2)0.026 (2)0.025 (2)0.010 (2)0.003 (2)0.0131 (19)
C70.023 (4)0.022 (3)0.029 (4)0.009 (3)0.003 (3)0.011 (3)
C7A0.022 (3)0.019 (3)0.017 (3)0.005 (3)0.001 (3)0.004 (3)
C80.019 (3)0.018 (3)0.028 (4)0.005 (3)0.003 (3)0.003 (3)
O80.020 (2)0.029 (2)0.034 (3)0.0098 (19)0.008 (2)0.013 (2)
C90.016 (3)0.030 (4)0.021 (3)0.009 (3)0.003 (3)0.001 (3)
C100.026 (3)0.025 (3)0.022 (3)0.013 (3)0.006 (3)0.001 (3)
C110.026 (3)0.019 (3)0.019 (3)0.009 (3)0.002 (3)0.007 (3)
C11A0.023 (4)0.014 (3)0.019 (3)0.005 (3)0.002 (3)0.001 (3)
C120.023 (4)0.018 (3)0.023 (4)0.005 (3)0.001 (3)0.005 (3)
C12A0.017 (3)0.020 (3)0.018 (3)0.007 (3)0.005 (3)0.003 (3)
C12B0.016 (3)0.023 (3)0.021 (3)0.006 (3)0.004 (3)0.005 (3)
C130.036 (2)0.028 (2)0.038 (2)0.0018 (19)0.0075 (19)0.0074 (19)
O1'0.030 (3)0.025 (2)0.034 (3)0.011 (2)0.008 (2)0.006 (2)
C1'0.021 (3)0.028 (4)0.024 (4)0.010 (3)0.003 (3)0.008 (3)
C2'0.027 (3)0.029 (3)0.031 (4)0.011 (3)0.004 (3)0.009 (3)
C3'0.031 (3)0.025 (3)0.029 (3)0.006 (2)0.001 (3)0.007 (2)
C4'0.030 (4)0.037 (4)0.024 (4)0.009 (3)0.005 (3)0.016 (3)
C4A'0.024 (3)0.027 (3)0.021 (4)0.009 (3)0.006 (3)0.007 (3)
C5'0.024 (3)0.027 (3)0.021 (4)0.006 (3)0.002 (3)0.000 (3)
C6'0.028 (3)0.027 (3)0.017 (3)0.013 (3)0.006 (3)0.003 (3)
C6A'0.020 (3)0.020 (3)0.026 (4)0.004 (3)0.003 (3)0.002 (3)
O6A'0.037 (3)0.018 (2)0.033 (3)0.006 (2)0.008 (2)0.005 (2)
O7'0.014 (2)0.031 (3)0.031 (3)0.009 (2)0.004 (2)0.012 (2)
C7'0.018 (3)0.034 (4)0.018 (3)0.005 (3)0.004 (3)0.010 (3)
C7A'0.018 (3)0.016 (3)0.023 (3)0.007 (3)0.002 (3)0.000 (3)
C8'0.022 (3)0.014 (3)0.022 (3)0.003 (3)0.003 (3)0.002 (3)
O8'0.021 (2)0.024 (2)0.045 (3)0.008 (2)0.011 (2)0.016 (2)
C9'0.017 (3)0.018 (3)0.044 (4)0.006 (3)0.002 (3)0.001 (3)
C10'0.023 (3)0.030 (3)0.029 (4)0.009 (3)0.007 (3)0.005 (3)
C11'0.021 (3)0.022 (3)0.023 (3)0.006 (3)0.003 (3)0.000 (3)
C1A'0.013 (3)0.021 (3)0.019 (3)0.005 (3)0.001 (3)0.003 (3)
C12'0.014 (3)0.019 (3)0.023 (4)0.004 (3)0.003 (3)0.008 (3)
C2A'0.011 (3)0.027 (3)0.023 (4)0.004 (3)0.001 (3)0.007 (3)
C2B'0.015 (3)0.021 (3)0.020 (3)0.005 (3)0.003 (3)0.003 (3)
C13'0.028 (2)0.034 (2)0.032 (2)0.0066 (18)0.0002 (18)0.0026 (18)
Geometric parameters (Å, º) top
O1—C11.222 (6)O1'—C1'1.226 (6)
C1—C12B1.489 (6)C1'—C2B'1.485 (6)
C1—C21.499 (6)C1'—C2'1.499 (7)
C2—C31.516 (7)C2'—C3'1.526 (7)
C3—C131.518 (6)C3'—C4'1.520 (7)
C3—C41.519 (7)C3'—C13'1.529 (7)
C4—C4A1.503 (6)C4'—C4A'1.507 (6)
C4A—C51.393 (6)C4A'—C5'1.385 (7)
C4A—C12B1.404 (6)C4A'—C2B'1.408 (6)
C5—C61.381 (7)C5'—C6'1.362 (7)
C6—C6A1.385 (7)C6'—C6A'1.395 (6)
C6A—O6A1.364 (6)C6A'—O6A'1.369 (6)
C6A—C12A1.397 (6)C6A'—C2A'1.393 (6)
O7—C71.449 (6)O7'—C7'1.459 (6)
O7—C121.462 (6)O7'—C12'1.471 (6)
C7—C7A1.495 (7)C7'—C7A'1.492 (7)
C7A—C81.376 (6)C7A'—C1A'1.367 (6)
C7A—C11A1.392 (6)C7A'—C8'1.389 (6)
C8—O81.369 (6)C8'—O8'1.373 (6)
C8—C91.386 (6)C8'—C9'1.387 (7)
C9—C101.393 (7)C9'—C10'1.387 (7)
C10—C111.380 (7)C10'—C11'1.391 (7)
C11—C11A1.385 (6)C11'—C1A'1.370 (7)
C11A—C121.509 (6)C1A'—C12'1.516 (6)
C12—C12A1.507 (6)C12'—C2A'1.516 (6)
C12A—C12B1.414 (6)C2A'—C2B'1.420 (6)
O1—C1—C12B120.6 (5)O1'—C1'—C2B'121.8 (5)
O1—C1—C2120.2 (5)O1'—C1'—C2'118.1 (5)
C12B—C1—C2119.1 (4)C2B'—C1'—C2'120.1 (5)
C1—C2—C3115.4 (5)C1'—C2'—C3'116.3 (5)
C2—C3—C13111.6 (4)C4'—C3'—C2'108.0 (5)
C2—C3—C4107.0 (5)C4'—C3'—C13'111.9 (5)
C13—C3—C4111.7 (4)C2'—C3'—C13'111.9 (5)
C4A—C4—C3111.3 (5)C4A'—C4'—C3'113.5 (5)
C5—C4A—C12B118.5 (5)C5'—C4A'—C2B'118.0 (5)
C5—C4A—C4119.8 (5)C5'—C4A'—C4'120.6 (5)
C12B—C4A—C4121.7 (5)C2B'—C4A'—C4'121.4 (5)
C6—C5—C4A121.2 (5)C6'—C5'—C4A'122.1 (5)
C5—C6—C6A120.0 (5)C5'—C6'—C6A'120.2 (5)
O6A—C6A—C6115.2 (5)O6A'—C6A'—C2A'122.4 (5)
O6A—C6A—C12A123.4 (5)O6A'—C6A'—C6'117.0 (5)
C6—C6A—C12A121.4 (5)C2A'—C6A'—C6'120.6 (5)
C7—O7—C12107.4 (4)C7'—O7'—C12'107.3 (4)
O7—C7—C7A103.9 (4)O7'—C7'—C7A'102.8 (4)
C8—C7A—C11A120.3 (5)C1A'—C7A'—C8'120.6 (5)
C8—C7A—C7130.8 (5)C1A'—C7A'—C7'110.5 (4)
C11A—C7A—C7108.8 (4)C8'—C7A'—C7'128.8 (5)
O8—C8—C7A117.5 (5)O8'—C8'—C9'123.7 (5)
O8—C8—C9123.2 (5)O8'—C8'—C7A'117.8 (5)
C7A—C8—C9119.3 (5)C9'—C8'—C7A'118.5 (5)
C8—C9—C10119.7 (5)C10'—C9'—C8'120.3 (5)
C11—C10—C9121.7 (5)C9'—C10'—C11'120.5 (6)
C10—C11—C11A117.7 (5)C1A'—C11'—C10'118.5 (5)
C11—C11A—C7A121.3 (5)C7A'—C1A'—C11'121.5 (5)
C11—C11A—C12130.3 (5)C7A'—C1A'—C12'108.0 (4)
C7A—C11A—C12108.2 (4)C11'—C1A'—C12'130.4 (5)
O7—C12—C12A110.0 (4)O7'—C12'—C1A'102.3 (4)
O7—C12—C11A103.0 (4)O7'—C12'—C2A'110.2 (4)
C12A—C12—C11A116.8 (5)C1A'—C12'—C2A'117.5 (5)
C6A—C12A—C12B117.8 (5)C6A'—C2A'—C2B'118.0 (5)
C6A—C12A—C12120.4 (4)C6A'—C2A'—C12'120.7 (4)
C12B—C12A—C12121.8 (4)C2B'—C2A'—C12'121.3 (5)
C4A—C12B—C12A121.2 (5)C4A'—C2B'—C2A'121.0 (5)
C4A—C12B—C1116.8 (4)C4A'—C2B'—C1'117.3 (4)
C12A—C12B—C1122.0 (4)C2A'—C2B'—C1'121.7 (5)
(gelb) top
Crystal data top
C33H24Br2O6F(000) = 680
Mr = 676.34Dx = 1.638 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.796 (2) ÅCell parameters from 54 reflections
b = 7.914 (2) Åθ = 10–12.5°
c = 22.243 (2) ŵ = 3.00 mm1
β = 92.12 (2)°T = 153 K
V = 1371.4 (5) Å3Blocks, yellow
Z = 20.4 × 0.2 × 0.2 mm
Data collection top
Stoe-Siemes-Huber AED2 four-circle
diffractometer
4144 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 25.1°, θmin = 3.1°
profile data from 2theata/ω scansh = 99
Absorption correction: ψ scan
SHEXTL 5.1 (Sheldrick, 1998)
k = 99
Tmin = 0.203, Tmax = 0.273l = 2626
6184 measured reflections3 standard reflections every 90 min
4870 independent reflections
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)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097 w = 1/[σ2(Fo2) + (0.0439P)2 + 1.0045P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4870 reflectionsΔρmax = 0.37 e Å3
371 parametersΔρmin = 0.61 e Å3
1 restraintAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.017 (10)
Crystal data top
C33H24Br2O6V = 1371.4 (5) Å3
Mr = 676.34Z = 2
Monoclinic, P21Mo Kα radiation
a = 7.796 (2) ŵ = 3.00 mm1
b = 7.914 (2) ÅT = 153 K
c = 22.243 (2) Å0.4 × 0.2 × 0.2 mm
β = 92.12 (2)°
Data collection top
Stoe-Siemes-Huber AED2 four-circle
diffractometer
4870 independent reflections
Absorption correction: ψ scan
SHEXTL 5.1 (Sheldrick, 1998)
4144 reflections with I > 2σ(I)
Tmin = 0.203, Tmax = 0.273Rint = 0.039
6184 measured reflections3 standard reflections every 90 min
Refinement top
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097Δρmax = 0.37 e Å3
S = 1.03Δρmin = 0.61 e Å3
4870 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
371 parametersAbsolute structure parameter: 0.017 (10)
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
Br10.53656 (7)0.26337 (10)0.62293 (3)0.0618 (2)
Br20.84803 (7)0.38811 (8)0.53382 (3)0.05315 (18)
O10.8591 (4)0.0143 (4)0.91404 (13)0.0246 (7)
O71.0971 (4)0.0192 (4)0.85444 (13)0.0254 (7)
O6A0.5546 (4)0.4198 (4)0.82114 (13)0.0242 (7)
O1'0.6948 (4)0.3811 (6)0.73638 (15)0.0431 (10)
O80.9624 (4)0.1616 (4)0.69371 (14)0.0286 (7)
O11'0.8264 (5)0.0459 (5)0.61244 (16)0.0475 (11)
C11.0182 (5)0.0994 (7)0.90366 (19)0.0223 (9)
C21.1465 (5)0.0968 (7)0.95567 (19)0.0278 (10)
H2A1.08940.12630.99330.033*
H2B1.19630.01770.96030.033*
C31.2901 (5)0.2260 (6)0.94372 (19)0.0266 (11)
H31.34280.19320.90510.032*
C131.4310 (6)0.2182 (7)0.9931 (2)0.0363 (12)
H13A1.47530.10260.99630.054*
H13B1.52450.29500.98310.054*
H13C1.38400.25221.03150.054*
C41.2220 (6)0.4080 (6)0.9361 (2)0.0262 (10)
H4A1.30790.47530.91480.031*
H4B1.21080.45850.97650.031*
C4A1.0527 (6)0.4224 (6)0.90237 (19)0.0232 (10)
C50.9705 (6)0.5720 (6)0.88573 (19)0.0255 (11)
H51.02730.67660.89290.031*
C60.8072 (6)0.5714 (6)0.85882 (19)0.0248 (10)
H60.75580.67530.84650.030*
C6A0.7185 (5)0.4229 (6)0.84966 (19)0.0231 (10)
C71.0241 (5)0.0468 (6)0.79540 (19)0.0264 (10)
H7A1.01490.17020.78880.032*
H7B1.10510.00240.76600.032*
C7A0.8499 (5)0.0307 (6)0.78141 (19)0.0218 (10)
C80.8213 (6)0.1269 (6)0.7295 (2)0.0265 (10)
C90.6627 (6)0.1978 (6)0.7138 (2)0.0295 (11)
H90.64980.26770.67920.035*
C100.5240 (6)0.1655 (7)0.7490 (2)0.0315 (12)
H100.41390.21010.73820.038*
C110.5475 (6)0.0670 (6)0.8004 (2)0.0270 (11)
H110.45250.04350.82470.032*
C11A0.7071 (6)0.0031 (6)0.8165 (2)0.0229 (10)
C120.7286 (5)0.0928 (6)0.87512 (18)0.0230 (10)
H120.61700.09350.89590.028*
C12A0.7930 (5)0.2728 (6)0.86923 (17)0.0198 (9)
C12B0.9590 (5)0.2764 (6)0.89062 (17)0.0203 (9)
C1'0.5601 (6)0.3978 (6)0.7598 (2)0.0258 (11)
C2'0.3883 (5)0.3991 (6)0.7300 (2)0.0228 (10)
C3'0.3591 (6)0.3446 (6)0.6709 (2)0.0285 (11)
C4'0.1966 (6)0.3449 (7)0.6446 (2)0.0358 (13)
H4'0.17840.30550.60460.043*
C5'0.0612 (6)0.4023 (7)0.6763 (2)0.0338 (12)
H5'0.05110.40120.65820.041*
C6'0.0860 (6)0.4615 (6)0.7343 (2)0.0306 (11)
H6'0.00770.50420.75580.037*
C7'0.2488 (6)0.4580 (6)0.7605 (2)0.0266 (11)
H7'0.26580.49710.80070.032*
C11'0.9444 (6)0.1224 (6)0.6340 (2)0.0293 (11)
C12'1.0921 (6)0.1860 (6)0.6006 (2)0.0273 (11)
C13'1.0679 (6)0.3003 (7)0.5533 (2)0.0318 (12)
C14'1.2035 (7)0.3562 (8)0.5205 (2)0.0421 (15)
H14'1.18540.43520.48880.051*
C15'1.3655 (7)0.2954 (8)0.5346 (2)0.0443 (15)
H15'1.45940.33200.51190.053*
C16'1.3937 (6)0.1837 (8)0.5805 (2)0.0459 (16)
H16'1.50620.14250.58940.055*
C17'1.2571 (6)0.1302 (8)0.6141 (2)0.0373 (12)
H17'1.27740.05440.64670.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0324 (3)0.1028 (6)0.0505 (4)0.0027 (3)0.0055 (2)0.0425 (4)
Br20.0428 (3)0.0585 (4)0.0576 (4)0.0067 (3)0.0058 (3)0.0178 (3)
O10.0250 (16)0.0265 (18)0.0222 (17)0.0002 (14)0.0006 (13)0.0055 (14)
O70.0271 (16)0.0251 (18)0.0240 (17)0.0048 (14)0.0003 (13)0.0059 (14)
O6A0.0216 (15)0.0275 (18)0.0237 (16)0.0057 (13)0.0028 (12)0.0023 (14)
O1'0.0207 (16)0.078 (3)0.0302 (19)0.0004 (18)0.0002 (14)0.008 (2)
O80.0311 (16)0.034 (2)0.0211 (16)0.0055 (15)0.0035 (13)0.0022 (14)
O11'0.045 (2)0.066 (3)0.0320 (19)0.026 (2)0.0106 (16)0.015 (2)
C10.024 (2)0.024 (2)0.019 (2)0.002 (2)0.0008 (16)0.002 (2)
C20.032 (2)0.028 (2)0.024 (2)0.004 (2)0.0002 (18)0.002 (2)
C30.026 (2)0.035 (3)0.019 (2)0.007 (2)0.0022 (17)0.002 (2)
C130.031 (2)0.042 (3)0.036 (3)0.003 (2)0.004 (2)0.001 (2)
C40.029 (2)0.023 (3)0.026 (2)0.001 (2)0.0006 (19)0.002 (2)
C4A0.026 (2)0.026 (3)0.018 (2)0.001 (2)0.0042 (17)0.004 (2)
C50.031 (2)0.024 (3)0.022 (2)0.001 (2)0.0003 (19)0.0022 (19)
C60.033 (2)0.017 (3)0.024 (2)0.0059 (19)0.0010 (18)0.0006 (18)
C6A0.019 (2)0.030 (3)0.021 (2)0.005 (2)0.0026 (17)0.001 (2)
C70.027 (2)0.029 (3)0.024 (2)0.005 (2)0.0064 (18)0.001 (2)
C7A0.025 (2)0.021 (3)0.019 (2)0.0015 (19)0.0028 (18)0.0059 (19)
C80.028 (2)0.030 (3)0.022 (2)0.002 (2)0.0022 (18)0.001 (2)
C90.033 (2)0.027 (3)0.028 (3)0.001 (2)0.003 (2)0.001 (2)
C100.035 (3)0.034 (3)0.025 (3)0.008 (2)0.006 (2)0.004 (2)
C110.027 (2)0.030 (3)0.025 (2)0.002 (2)0.0037 (19)0.004 (2)
C11A0.027 (2)0.018 (2)0.024 (2)0.0010 (19)0.0012 (18)0.0015 (19)
C120.021 (2)0.027 (3)0.021 (2)0.003 (2)0.0031 (16)0.003 (2)
C12A0.0216 (19)0.022 (2)0.016 (2)0.0015 (19)0.0035 (15)0.0030 (19)
C12B0.025 (2)0.021 (2)0.015 (2)0.007 (2)0.0029 (16)0.0005 (19)
C1'0.026 (2)0.026 (3)0.025 (2)0.002 (2)0.0025 (19)0.001 (2)
C2'0.023 (2)0.017 (2)0.029 (2)0.0020 (18)0.0025 (18)0.003 (2)
C3'0.028 (2)0.028 (3)0.030 (3)0.000 (2)0.0039 (19)0.003 (2)
C4'0.031 (3)0.051 (4)0.025 (3)0.002 (2)0.003 (2)0.002 (2)
C5'0.029 (2)0.040 (3)0.032 (3)0.002 (2)0.006 (2)0.008 (2)
C6'0.021 (2)0.038 (3)0.033 (3)0.000 (2)0.0053 (19)0.008 (2)
C7'0.024 (2)0.032 (3)0.023 (2)0.003 (2)0.0000 (19)0.002 (2)
C11'0.034 (3)0.030 (3)0.024 (2)0.003 (2)0.005 (2)0.004 (2)
C12'0.028 (2)0.035 (3)0.019 (2)0.006 (2)0.0006 (18)0.004 (2)
C13'0.032 (2)0.041 (3)0.023 (2)0.006 (2)0.0019 (19)0.006 (2)
C14'0.052 (3)0.054 (4)0.020 (2)0.015 (3)0.000 (2)0.006 (3)
C15'0.037 (3)0.073 (4)0.023 (3)0.018 (3)0.007 (2)0.004 (3)
C16'0.025 (2)0.074 (5)0.039 (3)0.003 (3)0.001 (2)0.012 (3)
C17'0.034 (3)0.051 (3)0.027 (3)0.002 (3)0.004 (2)0.004 (2)
Geometric parameters (Å, º) top
Br1—C3'1.891 (5)C7A—C81.393 (6)
Br2—C13'1.885 (5)C7A—C11A1.401 (6)
O1—C11.437 (5)C8—C91.391 (6)
O1—C121.451 (5)C9—C101.382 (7)
O7—C11.424 (5)C10—C111.391 (7)
O7—C71.428 (5)C11—C11A1.378 (6)
O6A—C1'1.378 (5)C11A—C121.512 (6)
O6A—C6A1.405 (5)C12—C12A1.518 (7)
O1'—C1'1.196 (5)C12A—C12B1.362 (5)
O8—C11'1.367 (5)C1'—C2'1.472 (6)
O8—C81.409 (5)C2'—C7'1.384 (6)
O11'—C11'1.187 (6)C2'—C3'1.395 (6)
C1—C12B1.500 (7)C3'—C4'1.375 (6)
C1—C21.501 (6)C4'—C5'1.369 (7)
C2—C31.546 (7)C5'—C6'1.379 (7)
C3—C131.525 (6)C6'—C7'1.377 (6)
C3—C41.542 (7)C11'—C12'1.480 (6)
C4—C4A1.498 (6)C12'—C17'1.382 (7)
C4A—C12B1.387 (6)C12'—C13'1.395 (7)
C4A—C51.389 (6)C13'—C14'1.379 (7)
C5—C61.387 (6)C14'—C15'1.377 (8)
C6—C6A1.375 (6)C15'—C16'1.361 (8)
C6A—C12A1.385 (6)C16'—C17'1.390 (7)
C7—C7A1.512 (6)
C1—O1—C12107.1 (3)O1—C12—C11A110.6 (4)
C1—O7—C7118.0 (3)O1—C12—C12A103.1 (3)
C1'—O6A—C6A112.9 (3)C11A—C12—C12A115.1 (4)
C11'—O8—C8116.9 (3)C12B—C12A—C6A118.3 (4)
O7—C1—O1108.3 (4)C12B—C12A—C12107.6 (4)
O7—C1—C12B113.9 (3)C6A—C12A—C12134.1 (4)
O1—C1—C12B102.0 (3)C12A—C12B—C4A124.7 (4)
O7—C1—C2107.0 (3)C12A—C12B—C1109.3 (4)
O1—C1—C2115.1 (4)C4A—C12B—C1125.8 (4)
C12B—C1—C2110.7 (4)O1'—C1'—O6A120.3 (4)
C1—C2—C3108.9 (4)O1'—C1'—C2'127.2 (4)
C13—C3—C4110.7 (4)O6A—C1'—C2'112.5 (4)
C13—C3—C2110.9 (4)C7'—C2'—C3'117.5 (4)
C4—C3—C2112.8 (4)C7'—C2'—C1'120.1 (4)
C4A—C4—C3114.8 (4)C3'—C2'—C1'122.4 (4)
C12B—C4A—C5115.2 (4)C4'—C3'—C2'121.0 (4)
C12B—C4A—C4118.6 (4)C4'—C3'—Br1116.3 (4)
C5—C4A—C4126.0 (4)C2'—C3'—Br1122.7 (3)
C6—C5—C4A121.3 (4)C5'—C4'—C3'119.8 (5)
C6A—C6—C5121.0 (4)C4'—C5'—C6'120.7 (4)
C6—C6A—C12A118.9 (4)C7'—C6'—C5'119.0 (5)
C6—C6A—O6A121.7 (4)C6'—C7'—C2'121.9 (4)
C12A—C6A—O6A119.4 (4)O11'—C11'—O8123.9 (4)
O7—C7—C7A116.8 (4)O11'—C11'—C12'125.2 (4)
C8—C7A—C11A116.1 (4)O8—C11'—C12'110.9 (4)
C8—C7A—C7120.5 (4)C17'—C12'—C13'118.0 (4)
C11A—C7A—C7123.3 (4)C17'—C12'—C11'121.2 (4)
C9—C8—C7A122.9 (4)C13'—C12'—C11'120.8 (4)
C9—C8—O8118.9 (4)C14'—C13'—C12'121.5 (5)
C7A—C8—O8118.1 (4)C14'—C13'—Br2117.9 (4)
C10—C9—C8119.3 (5)C12'—C13'—Br2120.6 (3)
C9—C10—C11119.2 (4)C15'—C14'—C13'118.8 (5)
C11A—C11—C10120.7 (4)C16'—C15'—C14'121.3 (5)
C11—C11A—C7A121.8 (4)C15'—C16'—C17'119.7 (5)
C11—C11A—C12118.6 (4)C12'—C17'—C16'120.7 (5)
C7A—C11A—C12119.6 (4)
(salbei) top
Crystal data top
C26H19BrO5Z = 2
Mr = 491.32F(000) = 500
Triclinic, P1Dx = 1.565 Mg m3
a = 8.279 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.539 (3) ÅCell parameters from 43 reflections
c = 11.962 (3) Åθ = 10–12.5°
α = 101.32 (2)°µ = 2.01 mm1
β = 110.25 (2)°T = 153 K
γ = 92.76 (2)°Blocks, colourless
V = 1042.9 (5) Å30.4 × 0.2 × 0.2 mm
Data collection top
Stoe-Siemens AED2 four-circle)
diffractometer
5946 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.000
Graphite monochromatorθmax = 25.1°, θmin = 3.0°
profile data from 2θ/ω scansh = 99
Absorption correction: ψ scan
SHELXTL 5.1 (Sheldrick, 1998)
k = 1313
Tmin = 0.376, Tmax = 0.426l = 1414
6304 measured reflections3 standard reflections every 90 min
6304 independent reflections
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)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.030P)2 + 1.3P]
where P = (Fo2 + 2Fc2)/3
S = 1.30(Δ/σ)max < 0.001
6304 reflectionsΔρmax = 0.41 e Å3
579 parametersΔρmin = 0.41 e Å3
96 restraintsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.009 (11)
Crystal data top
C26H19BrO5γ = 92.76 (2)°
Mr = 491.32V = 1042.9 (5) Å3
Triclinic, P1Z = 2
a = 8.279 (2) ÅMo Kα radiation
b = 11.539 (3) ŵ = 2.01 mm1
c = 11.962 (3) ÅT = 153 K
α = 101.32 (2)°0.4 × 0.2 × 0.2 mm
β = 110.25 (2)°
Data collection top
Stoe-Siemens AED2 four-circle)
diffractometer
6304 independent reflections
Absorption correction: ψ scan
SHELXTL 5.1 (Sheldrick, 1998)
5946 reflections with I > 2σ(I)
Tmin = 0.376, Tmax = 0.426Rint = 0.000
6304 measured reflections3 standard reflections every 90 min
Refinement top
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089Δρmax = 0.41 e Å3
S = 1.30Δρmin = 0.41 e Å3
6304 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
579 parametersAbsolute structure parameter: 0.009 (11)
96 restraints
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
Br11.08650 (6)1.05612 (4)1.14244 (4)0.0317 (2)
O11.2784 (7)0.5963 (5)0.3668 (5)0.0329 (14)
C11.1493 (9)0.5246 (6)0.3032 (6)0.0240 (16)
C21.1498 (7)0.4276 (5)0.1996 (5)0.0282 (13)
H2A1.14530.34980.22230.034*
H2B1.25900.44050.18470.034*
C30.9955 (7)0.4248 (5)0.0826 (4)0.0251 (11)
H31.00620.50230.05870.030*
C160.9931 (12)0.3249 (7)0.0228 (7)0.0314 (19)
H16A0.90700.33510.09940.047*
H16B0.96270.24780.00770.047*
H16C1.10810.32760.02910.047*
C40.8257 (9)0.4121 (6)0.1044 (6)0.0261 (17)
H4A0.73410.43710.03830.031*
H4B0.79280.32680.09830.031*
C4A0.8290 (9)0.4829 (7)0.2264 (6)0.0231 (18)
C50.6716 (9)0.4943 (7)0.2440 (6)0.0254 (18)
H50.56510.46480.17780.030*
C60.6708 (10)0.5485 (6)0.3579 (6)0.0264 (19)
H60.56350.55460.36960.032*
C6A0.8235 (9)0.5935 (6)0.4539 (5)0.0201 (16)
O6A0.8105 (7)0.6445 (5)0.5645 (4)0.0247 (12)
C70.9762 (9)0.6934 (6)0.6610 (6)0.0247 (17)
H70.96580.70880.74330.030*
O71.0988 (7)0.6159 (4)0.6545 (4)0.0258 (13)
C7A1.0475 (10)0.8052 (5)0.6376 (6)0.0234 (17)
C81.0233 (10)0.9238 (5)0.6652 (7)0.0254 (18)
O80.9113 (7)0.9580 (5)0.7270 (5)0.0280 (13)
C91.1014 (11)1.0080 (6)0.6261 (7)0.0288 (19)
H91.08551.08950.64550.035*
C101.2038 (11)0.9717 (6)0.5580 (7)0.0277 (19)
H101.25671.02920.53020.033*
C111.2302 (11)0.8538 (6)0.5299 (7)0.0287 (19)
H111.30060.82960.48360.034*
C121.1507 (10)0.7720 (5)0.5713 (6)0.0242 (18)
C131.1407 (10)0.6378 (6)0.5511 (6)0.0269 (19)
H131.24960.60650.54700.032*
C140.9823 (9)0.5859 (6)0.4391 (5)0.0212 (17)
C150.9843 (8)0.5306 (6)0.3232 (5)0.0202 (16)
C1'0.9692 (9)0.9577 (8)0.8488 (6)0.033 (2)
O1'1.1139 (8)0.9454 (9)0.9035 (6)0.086 (3)
C2'0.8275 (9)0.9766 (6)0.8961 (6)0.0272 (19)
C3'0.8583 (8)1.0134 (6)1.0215 (5)0.0237 (18)
C4'0.7245 (9)1.0224 (6)1.0646 (6)0.0260 (19)
H4'0.74821.04761.14980.031*
C5'0.5563 (11)0.9946 (7)0.9834 (7)0.033 (2)
H5'0.46351.00021.01300.040*
C6'0.5205 (10)0.9585 (7)0.8592 (6)0.0278 (18)
H6'0.40380.93950.80350.033*
C7'0.6549 (10)0.9503 (7)0.8169 (7)0.033 (2)
H7'0.62960.92620.73140.040*
Br21.51559 (5)0.21961 (4)0.27707 (4)0.03030 (19)
O1011.3171 (8)0.6661 (5)1.0570 (5)0.0364 (15)
C1011.4451 (9)0.7321 (6)1.1265 (6)0.0234 (16)
C1021.4442 (7)0.8068 (5)1.2456 (5)0.0278 (13)
H10A1.33560.84411.22830.033*
H10B1.44290.75341.30080.033*
C1031.5955 (7)0.9032 (5)1.3113 (4)0.0265 (12)
H1031.58470.96451.26130.032*
C1161.5946 (12)0.9642 (7)1.4375 (7)0.035 (2)
H11A1.69761.02341.48040.052*
H11B1.59560.90431.48550.052*
H11C1.48991.00381.42700.052*
C1041.7621 (9)0.8508 (6)1.3217 (6)0.0251 (17)
H10C1.86090.91511.36160.030*
H10D1.77720.79271.37430.030*
C14A1.7649 (8)0.7896 (6)1.1995 (6)0.0203 (17)
C1051.9175 (9)0.7805 (6)1.1787 (6)0.0217 (17)
H1052.02350.81091.24520.026*
C1061.9249 (9)0.7296 (6)1.0665 (6)0.0211 (17)
H1062.03270.72471.05520.025*
C16A1.7680 (9)0.6855 (6)0.9701 (5)0.0218 (17)
O16A1.7810 (7)0.6349 (4)0.8580 (4)0.0275 (13)
C1071.6162 (9)0.5877 (6)0.7616 (6)0.0286 (19)
H1071.62660.57490.67930.034*
O1071.4950 (7)0.6647 (5)0.7704 (5)0.0282 (13)
C17A1.5445 (10)0.4742 (5)0.7813 (6)0.0233 (17)
C1081.5701 (10)0.3572 (6)0.7519 (7)0.0264 (18)
O1081.6827 (8)0.3238 (5)0.6899 (5)0.0316 (14)
C1091.4904 (11)0.2714 (6)0.7883 (7)0.0304 (19)
H1091.50560.19000.76650.037*
C1101.3881 (11)0.3047 (6)0.8568 (7)0.033 (2)
H1101.33410.24550.88210.040*
C1111.3629 (10)0.4229 (6)0.8893 (6)0.0245 (17)
H1111.29530.44550.93810.029*
C1121.4391 (9)0.5069 (6)0.8484 (6)0.0234 (17)
C1131.4505 (9)0.6398 (5)0.8716 (5)0.0205 (16)
H1131.34160.67120.87570.025*
C1141.6100 (8)0.6906 (6)0.9855 (5)0.0210 (17)
C1151.6096 (8)0.7387 (6)1.1025 (5)0.0197 (16)
C11'1.6287 (9)0.3264 (8)0.5693 (6)0.032 (2)
O11'1.4891 (8)0.3521 (6)0.5165 (6)0.0445 (15)
C12'1.7702 (8)0.3051 (6)0.5219 (5)0.0222 (17)
C13'1.7410 (9)0.2635 (6)0.3976 (5)0.0244 (19)
C14'1.8795 (10)0.2505 (7)0.3597 (7)0.030 (2)
H14'1.85850.22220.27520.035*
C15'2.0476 (9)0.2776 (6)0.4417 (6)0.0260 (18)
H15'2.14150.26650.41390.031*
C16'2.0798 (10)0.3211 (7)0.5643 (7)0.0305 (19)
H16'2.19560.34200.62120.037*
C17'1.9412 (8)0.3340 (7)0.6036 (6)0.0238 (17)
H17'1.96340.36330.68810.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0304 (5)0.0352 (4)0.0218 (4)0.0032 (3)0.0035 (3)0.0016 (3)
O10.016 (3)0.047 (3)0.031 (3)0.001 (2)0.008 (3)0.001 (2)
C10.017 (4)0.026 (3)0.028 (3)0.005 (3)0.006 (3)0.009 (2)
C20.018 (3)0.038 (3)0.029 (3)0.009 (2)0.009 (2)0.007 (2)
C30.023 (3)0.028 (3)0.024 (2)0.004 (2)0.008 (2)0.009 (2)
C160.030 (5)0.038 (4)0.028 (4)0.003 (3)0.015 (4)0.004 (3)
C40.018 (4)0.038 (4)0.019 (3)0.005 (3)0.003 (3)0.006 (3)
C4A0.021 (5)0.028 (4)0.021 (3)0.006 (3)0.007 (3)0.009 (3)
C50.012 (5)0.038 (4)0.025 (4)0.002 (3)0.003 (3)0.011 (3)
C60.025 (6)0.028 (4)0.035 (4)0.012 (4)0.017 (4)0.012 (3)
C6A0.018 (5)0.021 (3)0.021 (4)0.000 (3)0.008 (3)0.003 (3)
O6A0.013 (3)0.036 (3)0.023 (3)0.001 (2)0.006 (2)0.004 (2)
C70.018 (5)0.035 (4)0.018 (4)0.005 (3)0.003 (3)0.005 (3)
O70.026 (4)0.033 (3)0.018 (3)0.002 (2)0.008 (2)0.007 (2)
C7A0.016 (5)0.035 (4)0.014 (4)0.001 (3)0.002 (3)0.003 (3)
C80.025 (5)0.033 (4)0.018 (4)0.005 (4)0.009 (4)0.001 (3)
O80.022 (3)0.040 (3)0.021 (3)0.007 (2)0.007 (2)0.006 (2)
C90.034 (6)0.032 (4)0.019 (4)0.001 (4)0.007 (4)0.007 (3)
C100.026 (5)0.037 (4)0.024 (4)0.001 (4)0.012 (4)0.010 (3)
C110.028 (6)0.037 (4)0.021 (4)0.004 (4)0.014 (4)0.001 (3)
C120.026 (5)0.026 (4)0.016 (4)0.002 (3)0.005 (3)0.001 (3)
C130.027 (5)0.036 (4)0.019 (4)0.001 (4)0.011 (4)0.005 (3)
C140.021 (5)0.023 (3)0.019 (4)0.005 (3)0.007 (3)0.005 (3)
C150.018 (4)0.025 (3)0.017 (3)0.005 (3)0.004 (3)0.009 (3)
C1'0.026 (6)0.046 (5)0.019 (4)0.005 (4)0.005 (4)0.004 (3)
O1'0.021 (4)0.207 (9)0.019 (3)0.028 (4)0.006 (3)0.002 (4)
C2'0.032 (6)0.024 (4)0.023 (4)0.004 (4)0.009 (4)0.001 (3)
C3'0.020 (5)0.026 (4)0.020 (4)0.001 (3)0.003 (4)0.004 (3)
C4'0.026 (5)0.028 (4)0.018 (4)0.005 (3)0.004 (3)0.001 (3)
C5'0.038 (6)0.037 (4)0.037 (5)0.011 (4)0.021 (4)0.019 (4)
C6'0.017 (5)0.033 (4)0.026 (4)0.001 (3)0.001 (4)0.004 (3)
C7'0.041 (6)0.037 (4)0.024 (4)0.010 (4)0.012 (4)0.011 (3)
Br20.0276 (5)0.0321 (4)0.0228 (4)0.0027 (3)0.0013 (3)0.0019 (3)
O1010.023 (4)0.049 (3)0.033 (3)0.001 (3)0.012 (3)0.002 (3)
C1010.020 (4)0.028 (3)0.021 (3)0.004 (3)0.007 (3)0.005 (2)
C1020.024 (3)0.040 (3)0.023 (3)0.010 (3)0.011 (2)0.007 (2)
C1030.032 (3)0.029 (3)0.023 (2)0.008 (2)0.012 (2)0.009 (2)
C1160.038 (6)0.040 (4)0.026 (4)0.002 (4)0.016 (4)0.002 (3)
C1040.028 (5)0.026 (3)0.021 (3)0.001 (3)0.008 (3)0.005 (3)
C14A0.018 (5)0.020 (3)0.023 (4)0.001 (3)0.005 (3)0.007 (3)
C1050.018 (5)0.018 (3)0.025 (4)0.001 (3)0.003 (3)0.003 (3)
C1060.009 (4)0.024 (4)0.026 (4)0.004 (3)0.002 (3)0.007 (3)
C16A0.023 (5)0.025 (3)0.020 (4)0.007 (3)0.009 (3)0.008 (3)
O16A0.029 (4)0.032 (3)0.024 (3)0.001 (3)0.015 (3)0.003 (2)
C1070.026 (5)0.038 (4)0.023 (4)0.001 (4)0.012 (4)0.007 (3)
O1070.023 (4)0.038 (3)0.024 (3)0.009 (3)0.006 (3)0.013 (2)
C17A0.020 (5)0.032 (4)0.016 (4)0.001 (3)0.006 (3)0.004 (3)
C1080.019 (5)0.037 (4)0.020 (4)0.001 (3)0.005 (3)0.004 (3)
O1080.034 (4)0.043 (3)0.020 (3)0.013 (3)0.014 (3)0.005 (2)
C1090.027 (6)0.026 (4)0.030 (4)0.001 (4)0.006 (4)0.002 (3)
C1100.032 (6)0.035 (4)0.023 (4)0.011 (4)0.002 (4)0.005 (3)
C1110.012 (5)0.037 (4)0.018 (4)0.005 (3)0.001 (3)0.002 (3)
C1120.007 (4)0.041 (4)0.015 (3)0.002 (3)0.001 (3)0.001 (3)
C1130.009 (4)0.032 (4)0.021 (4)0.005 (3)0.004 (3)0.008 (3)
C1140.013 (4)0.022 (3)0.027 (4)0.001 (3)0.004 (3)0.009 (3)
C1150.019 (4)0.016 (3)0.025 (4)0.004 (3)0.008 (3)0.004 (3)
C11'0.026 (5)0.046 (4)0.023 (4)0.013 (4)0.009 (4)0.006 (3)
O11'0.037 (4)0.068 (3)0.030 (3)0.022 (3)0.011 (3)0.015 (2)
C12'0.018 (5)0.029 (4)0.021 (4)0.008 (3)0.005 (4)0.009 (3)
C13'0.030 (6)0.017 (3)0.023 (4)0.004 (3)0.007 (4)0.004 (3)
C14'0.039 (6)0.029 (4)0.026 (4)0.013 (4)0.019 (4)0.005 (3)
C15'0.020 (5)0.027 (4)0.029 (4)0.006 (3)0.009 (3)0.000 (3)
C16'0.026 (6)0.036 (4)0.030 (4)0.007 (4)0.009 (4)0.011 (3)
C17'0.017 (5)0.032 (4)0.016 (4)0.000 (3)0.001 (3)0.000 (3)
Geometric parameters (Å, º) top
Br1—C3'1.908 (6)Br2—C13'1.892 (6)
O1—C11.229 (7)O101—C1011.207 (7)
C1—C151.468 (8)C101—C1151.488 (8)
C1—C21.499 (8)C101—C1021.516 (7)
C2—C31.527 (7)C102—C1031.505 (7)
C3—C41.521 (7)C103—C1041.509 (8)
C3—C161.526 (8)C103—C1161.538 (7)
C4—C4A1.516 (8)C104—C14A1.501 (7)
C4A—C151.396 (8)C14A—C1051.374 (8)
C4A—C51.398 (8)C14A—C1151.405 (7)
C5—C61.385 (8)C105—C1061.380 (8)
C6—C6A1.373 (8)C106—C16A1.395 (8)
C6A—O6A1.380 (7)C16A—C1141.385 (8)
C6A—C141.391 (8)C16A—O16A1.396 (7)
O6A—C71.451 (7)O16A—C1071.442 (7)
C7—O71.397 (7)C107—O1071.389 (8)
C7—C7A1.508 (7)C107—C17A1.506 (7)
O7—C131.458 (7)O107—C1131.456 (7)
C7A—C121.373 (8)C17A—C1081.373 (8)
C7A—C81.384 (7)C17A—C1121.394 (8)
C8—C91.382 (8)C108—C1091.382 (8)
C8—O81.399 (7)C108—O1081.403 (7)
O8—C1'1.368 (7)O108—C11'1.362 (7)
C9—C101.391 (8)C109—C1101.388 (9)
C10—C111.383 (8)C110—C1111.389 (8)
C11—C121.385 (8)C111—C1121.384 (7)
C12—C131.513 (7)C112—C1131.497 (7)
C13—C141.506 (8)C113—C1141.520 (7)
C14—C151.414 (7)C114—C1151.402 (7)
C1'—O1'1.181 (8)C11'—O11'1.193 (7)
C1'—C2'1.476 (8)C11'—C12'1.479 (8)
C2'—C7'1.393 (8)C12'—C17'1.393 (7)
C2'—C3'1.404 (8)C12'—C13'1.400 (8)
C3'—C4'1.374 (8)C13'—C14'1.375 (8)
C4'—C5'1.372 (8)C14'—C15'1.374 (8)
C5'—C6'1.382 (8)C15'—C16'1.379 (8)
C6'—C7'1.373 (9)C16'—C17'1.386 (8)
O1—C1—C15121.7 (6)O101—C101—C115122.0 (6)
O1—C1—C2122.2 (6)O101—C101—C102120.0 (6)
C15—C1—C2116.1 (5)C115—C101—C102117.9 (5)
C1—C2—C3111.4 (5)C103—C102—C101114.8 (5)
C4—C3—C16110.1 (5)C102—C103—C104109.3 (5)
C4—C3—C2110.7 (4)C102—C103—C116110.9 (5)
C16—C3—C2111.8 (5)C104—C103—C116111.6 (5)
C4A—C4—C3115.3 (5)C14A—C104—C103112.5 (5)
C15—C4A—C5119.4 (6)C105—C14A—C115117.8 (6)
C15—C4A—C4121.9 (6)C105—C14A—C104121.8 (6)
C5—C4A—C4118.6 (6)C115—C14A—C104120.4 (6)
C6—C5—C4A120.0 (7)C14A—C105—C106123.4 (6)
C6A—C6—C5120.7 (7)C105—C106—C16A117.4 (6)
C6—C6A—O6A116.8 (6)C114—C16A—C106121.9 (6)
C6—C6A—C14120.8 (6)C114—C16A—O16A122.4 (6)
O6A—C6A—C14122.5 (6)C106—C16A—O16A115.6 (6)
C6A—O6A—C7113.9 (5)C16A—O16A—C107113.9 (5)
O7—C7—O6A109.3 (5)O107—C107—O16A109.1 (6)
O7—C7—C7A103.3 (5)O107—C107—C17A103.6 (5)
O6A—C7—C7A110.1 (5)O16A—C107—C17A110.3 (6)
C7—O7—C13102.9 (5)C107—O107—C113103.5 (5)
C12—C7A—C8119.4 (5)C108—C17A—C112120.2 (6)
C12—C7A—C7107.3 (5)C108—C17A—C107133.2 (6)
C8—C7A—C7133.3 (6)C112—C17A—C107106.5 (5)
C9—C8—C7A120.4 (6)C17A—C108—C109119.9 (6)
C9—C8—O8119.4 (6)C17A—C108—O108120.9 (6)
C7A—C8—O8120.1 (6)C109—C108—O108119.2 (6)
C1'—O8—C8116.5 (6)C11'—O108—C108117.4 (6)
C8—C9—C10119.0 (6)C108—C109—C110119.6 (6)
C11—C10—C9121.5 (6)C109—C110—C111121.4 (6)
C10—C11—C12117.9 (6)C112—C111—C110118.1 (6)
C7A—C12—C11121.9 (6)C111—C112—C17A120.8 (6)
C7A—C12—C13105.8 (5)C111—C112—C113132.8 (6)
C11—C12—C13132.2 (6)C17A—C112—C113106.0 (5)
O7—C13—C14105.8 (5)O107—C113—C112102.3 (5)
O7—C13—C12102.2 (5)O107—C113—C114105.2 (5)
C14—C13—C12107.3 (6)C112—C113—C114107.6 (5)
C6A—C14—C15118.9 (6)C16A—C114—C115118.6 (6)
C6A—C14—C13115.9 (5)C16A—C114—C113115.7 (5)
C15—C14—C13125.2 (6)C115—C114—C113125.7 (6)
C4A—C15—C14120.1 (6)C114—C115—C14A120.6 (6)
C4A—C15—C1119.5 (5)C114—C115—C101120.3 (6)
C14—C15—C1120.3 (6)C14A—C115—C101119.1 (5)
O1'—C1'—O8122.1 (6)O11'—C11'—O108121.9 (6)
O1'—C1'—C2'127.8 (6)O11'—C11'—C12'127.2 (6)
O8—C1'—C2'110.1 (6)O108—C11'—C12'110.7 (6)
C7'—C2'—C3'117.0 (6)C17'—C12'—C13'118.1 (6)
C7'—C2'—C1'120.4 (6)C17'—C12'—C11'118.6 (6)
C3'—C2'—C1'122.4 (6)C13'—C12'—C11'123.2 (6)
C4'—C3'—C2'121.6 (6)C14'—C13'—C12'119.9 (6)
C4'—C3'—Br1115.8 (5)C14'—C13'—Br2117.6 (5)
C2'—C3'—Br1122.6 (5)C12'—C13'—Br2122.5 (5)
C5'—C4'—C3'119.5 (6)C15'—C14'—C13'121.3 (6)
C4'—C5'—C6'120.7 (7)C14'—C15'—C16'119.9 (7)
C7'—C6'—C5'119.5 (7)C15'—C16'—C17'119.2 (7)
C6'—C7'—C2'121.7 (7)C16'—C17'—C12'121.5 (6)

Experimental details

(ende3)(gelb)(salbei)
Crystal data
Chemical formulaC19H18O4C33H24Br2O6C26H19BrO5
Mr310.33676.34491.32
Crystal system, space groupTriclinic, P1Monoclinic, P21Triclinic, P1
Temperature (K)153153153
a, b, c (Å)8.075 (2), 8.871 (2), 11.606 (2)7.796 (2), 7.914 (2), 22.243 (2)8.279 (2), 11.539 (3), 11.962 (3)
α, β, γ (°)72.69 (3), 80.07 (3), 71.84 (3)90, 92.12 (2), 90101.32 (2), 110.25 (2), 92.76 (2)
V3)751.3 (3)1371.4 (5)1042.9 (5)
Z222
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.103.002.01
Crystal size (mm)0.4 × 0.2 × 0.20.4 × 0.2 × 0.20.4 × 0.2 × 0.2
Data collection
DiffractometerStoe-Siemens-Huber AED2 four-circle
diffractometer
Stoe-Siemes-Huber AED2 four-circle
diffractometer
Stoe-Siemens AED2 four-circle)
diffractometer
Absorption correctionψ scan
SHEXTL 5.1 (Sheldrick, 1998)
ψ scan
SHELXTL 5.1 (Sheldrick, 1998)
Tmin, Tmax0.203, 0.2730.376, 0.426
No. of measured, independent and
observed [I > 2σ(I)] reflections
5336, 5336, 4018 6184, 4870, 4144 6304, 6304, 5946
Rint0.0000.0390.000
(sin θ/λ)max1)0.5960.5960.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.118, 1.03 0.042, 0.097, 1.03 0.031, 0.089, 1.30
No. of reflections533648706304
No. of parameters421371579
No. of restraints68196
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.220.37, 0.610.41, 0.41
Absolute structureFlack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter3 (2)0.017 (10)0.009 (11)

Computer programs: DIF4 (Stoe & Cie, 1988a), REDU4 (Stoe & Cie, 1988b), SHELXS90 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL 5.1 (Sheldrick, 1998).

 
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