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The title compound, (1), is the product of a model synthesis of an analogue of the antibiotic medermycin, and is thought to be the result of an unusual 1,6-hydride shift.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800018092/ob6002sup1.cif
Contains datablocks 1, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800018092/ob60021sup2.hkl
Contains datablock 1

CCDC reference: 155875

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.036
  • wR factor = 0.114
  • Data-to-parameter ratio = 7.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
REFNR_01 Alert B Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX > 18 sine(theta)/lambda 0.5878 Proportion of unique data used 1.0000 Ratio reflections to parameters 7.7539
Yellow Alert Alert Level C:
THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5878 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 65.00 From the CIF: _reflns_number_total 2962 Count of symmetry unique reflns 2962 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Recent synthetic effort has been directed towards the synthesis of the pyranonaphthoquinone antibiotic medermycin (2) which was isolated from Streptomyces tanashiensis and contains a C-glycoside linkage to a 2-deoxy sugar (Takano et al., 1976). As part of this programme we embarked on model studies directed towards the synthesis of the 2-deoxyglucosyl analogue of medermycin (3). The key step in the approach to (3) involved the direct C-glycosylation of 3-bromonaphthol (4) with a 2-deoxyglucosyl donor (5) (Brimble and Brenstrum, 2000) (Scheme 1) which was expected to afford the desired C-glycoside (6). Unfortunately this critical C-glycosylation reaction afforded predominantly C-glycoside (1) wherein extensive rearrangement of the 2-deoxyglucosyl moiety had taken place. The structure of this rearranged C-glycoside was established by X-ray crystallography of the acetate derivative of the initial glycosylation product (Fig. 1).

The structure of this rearranged C-glycoside (1) clearly shows that extensive rearrangement of the carbohydrate skeleton has taken place. This rearrangement has been proposed to occur via an unusual 1,6-hydride shift similar to that observed by Steel et al. in the dimerization of tri-O-benzyl-D-glucal (Byerley et al.,1998). The X-ray structure also clearly establishes that the naphthalene ring is endo to the bicylic ring system

Experimental top

Trimethylsilyl trifluoromethanesulfonate (51 ml, 0.266 mmol) and silver perchlorate (2 mg, 5 mol%) were added to a stirred solution of 3-bromo-1,4-dimethoxy-5-hydroxynaphthalene (4) (50 mg, 0.177 mmol) and tri-O-benzyl-2-deoxy-D-glucosyl acetate (5) (101 mg, 210 mmol) in dry acetonitrile (5 ml) at 0 °C. The mixture was stirred for 1 h then quenched with aqueous bicarbonate solution (5 ml). The reaction mixture was extracted with dichloromethane (3 x 50 ml), washed with water (100 ml) and dried (magnesium sulfate). The solvent was removed at reduced pressure and the oily residue purified by flash chromatography using hexane-ethyl acetate (4:1) as eluent to give a mixture of a rearranged C-glycoside and b-C-glycoside (6) (71 mg, 6:1). This mixture of glycosides was subjected to HPLC.

Triethylamine (0.50 ml, 3.59 mmol), acetic anhydride (0.25 ml, 2.65 mmol) and a catalytic quantity of dimethylaminopyridine were added to a solution of the above rearranged C-glycoside (98 mg, 0.166 mmol) in dichloromethane (2 ml). The solution was stirred overnight then the solvent removed at reduced pressure. The residue was purified by flash chromatography using hexane-ethyl acetate (4:1) to give the acetate (1) (99 mg, 94%) which was recrystallized from hexane-ethyl acetate to give pale brown needles m.p. 477–478 K.

Computing details top

Data collection: MSC AFC Diffractometer Control (MSC, 1995); cell refinement: MSC AFC Diffractometer Control (MSC, 1995); data reduction: TEXSAN (MSC, 1992); program(s) used to solve structure: SIR92 (Altomare, et al. 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN for Windows (MSC, 1997).

Figures top
[Figure 1] Fig. 1. ORTEP (Johnson, 1976, Hall et al. 1999) projection of (1) with displacement ellipsoids shown at the 20% level.
(1) top
Crystal data top
C34H33BrO7Dx = 1.393 Mg m3
Mr = 633.51Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 25 reflections
a = 19.515 (1) Åθ = 26.6–30.2°
b = 23.667 (2) ŵ = 2.25 mm1
c = 6.541 (2) ÅT = 294 K
V = 3021.0 (10) Å3Acicular, pale brown
Z = 40.55 × 0.13 × 0.08 mm
F(000) = 1312
Data collection top
Rigaku AFC7R
diffractometer
2068 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.000
Graphite monochromatorθmax = 65.0°, θmin = 2.9°
ω–2θ scansh = 022
Absorption correction: ψ scan
(North et al., 1968)
k = 027
Tmin = 0.715, Tmax = 0.835l = 07
2962 measured reflections3 standard reflections every 150 reflections
2962 independent reflections intensity decay: 2.4%
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0579P)2 + 0.6329P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2962 reflectionsΔρmax = 0.31 e Å3
382 parametersΔρmin = 0.34 e Å3
0 restraintsAbsolute structure: Flack (1983) and Bernardinelli & Flack(1985); No Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (3)
Crystal data top
C34H33BrO7V = 3021.0 (10) Å3
Mr = 633.51Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 19.515 (1) ŵ = 2.25 mm1
b = 23.667 (2) ÅT = 294 K
c = 6.541 (2) Å0.55 × 0.13 × 0.08 mm
Data collection top
Rigaku AFC7R
diffractometer
2068 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.000
Tmin = 0.715, Tmax = 0.8353 standard reflections every 150 reflections
2962 measured reflections intensity decay: 2.4%
2962 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.114Δρmax = 0.31 e Å3
S = 1.02Δρmin = 0.34 e Å3
2962 reflectionsAbsolute structure: Flack (1983) and Bernardinelli & Flack(1985); No Friedel pairs
382 parametersAbsolute structure parameter: 0.06 (3)
0 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
Br10.96750 (3)0.09686 (3)0.05259 (13)0.0935 (3)
O10.56407 (16)0.20795 (14)0.4274 (6)0.0644 (9)
O20.56036 (17)0.34224 (14)0.5699 (7)0.0745 (11)
O30.54484 (19)0.18553 (15)0.8661 (7)0.0843 (12)
O40.74688 (16)0.23284 (14)0.1453 (5)0.0595 (8)
O50.8305 (2)0.26370 (16)0.3496 (7)0.0776 (11)
O60.85879 (17)0.18547 (15)0.0133 (6)0.0659 (9)
O70.8080 (2)0.00178 (14)0.4892 (8)0.0842 (13)
C10.6316 (2)0.2297 (2)0.3920 (8)0.0556 (11)
H10.63180.24930.26000.067*
C20.6533 (2)0.27178 (17)0.5577 (8)0.0519 (11)
H20.70350.27220.55970.062*
C30.6298 (2)0.25151 (19)0.7669 (8)0.0572 (12)
H3A0.65400.21700.80150.069*
H3B0.64140.27980.86850.069*
C40.5532 (3)0.2405 (2)0.7740 (9)0.0620 (13)
H40.53110.26900.86000.074*
C50.5235 (2)0.2429 (2)0.5625 (9)0.0629 (13)
H50.47790.22560.56990.075*
C60.5133 (3)0.3027 (2)0.4865 (11)0.0785 (17)
H6A0.51760.30300.33880.094*
H6B0.46710.31470.51990.094*
C70.6295 (2)0.33348 (18)0.5157 (10)0.0654 (14)
H70.63470.34120.36930.078*
C80.6720 (3)0.37487 (19)0.6311 (11)0.0693 (15)
C90.6497 (3)0.3983 (2)0.8139 (12)0.0847 (19)
H90.60660.38910.86410.102*
C100.6916 (4)0.4357 (2)0.9235 (15)0.102 (2)
H100.67580.45191.04420.123*
C110.7563 (4)0.4484 (3)0.8520 (17)0.108 (3)
H110.78480.47250.92560.130*
C120.7783 (4)0.4252 (3)0.6719 (17)0.101 (2)
H120.82180.43370.62290.122*
C130.7367 (3)0.3898 (2)0.5638 (13)0.0831 (18)
H130.75240.37510.44050.100*
C140.6804 (2)0.17996 (18)0.3789 (8)0.0535 (11)
C150.6690 (3)0.13042 (19)0.4902 (9)0.0621 (13)
H150.62890.12660.56580.075*
C160.7157 (3)0.08766 (19)0.4899 (10)0.0668 (14)
H160.70820.05600.57090.080*
C170.7755 (2)0.09084 (19)0.3677 (8)0.0583 (12)
C180.8241 (3)0.04559 (19)0.3654 (10)0.0656 (13)
C190.8813 (3)0.0487 (2)0.2487 (11)0.0741 (15)
H190.91390.02000.25240.089*
C200.8904 (2)0.0960 (2)0.1220 (8)0.0632 (12)
C210.8461 (2)0.1404 (2)0.1148 (8)0.0555 (11)
C220.7869 (2)0.13918 (18)0.2459 (8)0.0502 (11)
C230.7386 (2)0.18412 (19)0.2630 (8)0.0532 (11)
C240.7972 (3)0.2688 (2)0.1991 (10)0.0674 (14)
C250.8021 (3)0.3149 (3)0.0407 (14)0.104 (3)
H25A0.82770.34610.09530.156*
H25B0.75690.32750.00470.156*
H25C0.82480.30060.07880.156*
C260.8297 (3)0.1785 (4)0.2147 (9)0.103 (2)
H26A0.84410.14300.27080.154*
H26B0.84500.20860.30170.154*
H26C0.78060.17930.20540.154*
C270.8576 (3)0.0429 (2)0.5058 (13)0.096 (2)
H27A0.86680.05810.37250.144*
H27B0.83990.07220.59250.144*
H27C0.89920.02830.56330.144*
C280.4846 (3)0.1790 (2)0.9722 (12)0.0849 (18)
H28A0.44700.19510.89470.102*
H28B0.48750.19861.10220.102*
C290.4722 (3)0.1169 (2)1.0074 (9)0.0675 (14)
C300.4775 (3)0.0943 (3)1.2008 (10)0.0789 (16)
H300.49090.11731.30920.095*
C310.4632 (4)0.0379 (3)1.2355 (12)0.0911 (19)
H310.46570.02311.36700.109*
C320.4453 (3)0.0042 (3)1.0755 (15)0.094 (2)
H320.43520.03361.09840.113*
C330.4421 (4)0.0251 (3)0.8851 (14)0.097 (2)
H330.43020.00140.77720.116*
C340.4565 (4)0.0818 (3)0.8475 (11)0.0880 (19)
H340.45530.09580.71470.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0722 (4)0.0954 (4)0.1128 (5)0.0176 (3)0.0302 (4)0.0167 (4)
O10.0494 (17)0.069 (2)0.075 (2)0.0040 (15)0.0021 (18)0.0120 (19)
O20.0603 (19)0.0546 (18)0.109 (3)0.0108 (15)0.015 (2)0.007 (2)
O30.075 (2)0.062 (2)0.116 (3)0.0093 (18)0.031 (2)0.020 (2)
O40.0522 (17)0.0634 (18)0.063 (2)0.0027 (15)0.0038 (17)0.0188 (18)
O50.074 (2)0.067 (2)0.092 (3)0.0155 (19)0.013 (2)0.007 (2)
O60.0595 (19)0.078 (2)0.060 (2)0.0061 (16)0.0033 (17)0.0157 (19)
O70.082 (2)0.0570 (19)0.114 (4)0.0130 (17)0.022 (3)0.023 (2)
C10.055 (2)0.057 (3)0.055 (3)0.001 (2)0.001 (2)0.006 (2)
C20.048 (2)0.046 (2)0.061 (3)0.0033 (18)0.003 (2)0.005 (2)
C30.064 (3)0.044 (2)0.063 (3)0.003 (2)0.005 (3)0.003 (2)
C40.068 (3)0.049 (2)0.069 (3)0.005 (2)0.014 (3)0.007 (3)
C50.044 (2)0.067 (3)0.078 (3)0.001 (2)0.002 (3)0.000 (3)
C60.063 (3)0.072 (3)0.101 (5)0.006 (2)0.017 (3)0.009 (4)
C70.065 (3)0.047 (2)0.084 (4)0.002 (2)0.006 (3)0.012 (3)
C80.073 (3)0.040 (2)0.096 (4)0.005 (2)0.010 (3)0.012 (3)
C90.080 (4)0.053 (3)0.121 (6)0.009 (3)0.007 (4)0.010 (4)
C100.113 (5)0.057 (3)0.137 (7)0.015 (3)0.012 (5)0.022 (4)
C110.098 (5)0.050 (3)0.175 (9)0.006 (3)0.033 (6)0.007 (5)
C120.089 (4)0.058 (3)0.157 (8)0.009 (3)0.000 (5)0.013 (5)
C130.087 (4)0.050 (3)0.112 (5)0.014 (3)0.008 (4)0.012 (4)
C140.054 (2)0.049 (2)0.057 (3)0.004 (2)0.001 (2)0.002 (2)
C150.063 (3)0.056 (3)0.068 (3)0.004 (2)0.009 (3)0.003 (3)
C160.071 (3)0.049 (2)0.081 (4)0.004 (2)0.010 (3)0.006 (3)
C170.059 (2)0.048 (2)0.068 (3)0.003 (2)0.003 (2)0.002 (3)
C180.066 (3)0.049 (3)0.082 (4)0.001 (2)0.001 (3)0.006 (3)
C190.064 (3)0.069 (3)0.090 (4)0.013 (3)0.002 (3)0.010 (3)
C200.066 (3)0.058 (3)0.066 (3)0.003 (2)0.003 (2)0.002 (3)
C210.053 (2)0.061 (3)0.053 (3)0.002 (2)0.007 (2)0.001 (2)
C220.048 (2)0.047 (2)0.055 (3)0.0031 (18)0.004 (2)0.000 (2)
C230.054 (2)0.056 (2)0.050 (3)0.003 (2)0.011 (2)0.005 (2)
C240.056 (3)0.062 (3)0.084 (4)0.002 (2)0.005 (3)0.021 (3)
C250.082 (4)0.087 (4)0.143 (7)0.001 (3)0.016 (5)0.061 (5)
C260.092 (5)0.165 (7)0.052 (3)0.030 (5)0.005 (3)0.013 (4)
C270.099 (4)0.073 (4)0.117 (6)0.019 (3)0.014 (4)0.033 (4)
C280.095 (4)0.069 (3)0.091 (4)0.013 (3)0.024 (4)0.002 (3)
C290.069 (3)0.062 (3)0.072 (4)0.011 (2)0.015 (3)0.005 (3)
C300.090 (4)0.071 (3)0.076 (4)0.001 (3)0.013 (3)0.005 (3)
C310.107 (5)0.071 (4)0.095 (5)0.002 (4)0.016 (5)0.010 (4)
C320.084 (4)0.062 (3)0.135 (7)0.012 (3)0.013 (5)0.013 (5)
C330.100 (5)0.074 (4)0.117 (6)0.020 (3)0.004 (4)0.019 (4)
C340.109 (5)0.080 (4)0.075 (4)0.016 (4)0.004 (4)0.002 (3)
Geometric parameters (Å, º) top
Br1—C201.889 (5)C12—H120.9300
O1—C11.434 (5)C13—H130.9300
O1—C51.447 (6)C14—C231.370 (6)
O2—C71.411 (6)C14—C151.398 (6)
O2—C61.421 (6)C15—C161.362 (7)
O3—C281.373 (7)C15—H150.9300
O3—C41.442 (6)C16—C171.416 (7)
O4—C241.346 (7)C16—H160.9300
O4—C231.396 (5)C17—C221.412 (7)
O5—C241.187 (7)C17—C181.430 (6)
O6—C211.380 (6)C18—C191.355 (8)
O6—C261.444 (7)C19—C201.404 (7)
O7—C181.352 (6)C19—H190.9300
O7—C271.437 (6)C20—C211.361 (7)
C1—C141.516 (6)C21—C221.438 (7)
C1—C21.531 (7)C22—C231.426 (6)
C1—H10.9800C24—C251.508 (8)
C2—C31.521 (7)C25—H25A0.9600
C2—C71.557 (6)C25—H25B0.9600
C2—H20.9800C25—H25C0.9600
C3—C41.519 (7)C26—H26A0.9600
C3—H3A0.9700C26—H26B0.9600
C3—H3B0.9700C26—H26C0.9600
C4—C51.501 (8)C27—H27A0.9600
C4—H40.9800C27—H27B0.9600
C5—C61.512 (7)C27—H27C0.9600
C5—H50.9800C28—C291.508 (7)
C6—H6A0.9700C28—H28A0.9700
C6—H6B0.9700C28—H28B0.9700
C7—C81.489 (8)C29—C341.370 (8)
C7—H70.9800C29—C301.377 (9)
C8—C131.383 (8)C30—C311.383 (8)
C8—C91.388 (9)C30—H300.9300
C9—C101.401 (9)C31—C321.361 (11)
C9—H90.9300C31—H310.9300
C10—C111.381 (10)C32—C331.341 (11)
C10—H100.9300C32—H320.9300
C11—C121.369 (12)C33—C341.393 (9)
C11—H110.9300C33—H330.9300
C12—C131.365 (10)C34—H340.9300
C1—O1—C5113.3 (4)C14—C15—H15119.5
C7—O2—C6115.2 (4)C15—C16—C17120.9 (5)
C28—O3—C4114.1 (4)C15—C16—H16119.6
C24—O4—C23117.6 (4)C17—C16—H16119.6
C21—O6—C26113.3 (5)C22—C17—C16119.4 (4)
C18—O7—C27117.0 (4)C22—C17—C18119.8 (4)
O1—C1—C14107.9 (4)C16—C17—C18120.8 (5)
O1—C1—C2111.9 (4)O7—C18—C19124.7 (5)
C14—C1—C2111.8 (4)O7—C18—C17114.5 (5)
O1—C1—H1108.4C19—C18—C17120.8 (5)
C14—C1—H1108.4C18—C19—C20118.7 (5)
C2—C1—H1108.4C18—C19—H19120.7
C3—C2—C1110.4 (3)C20—C19—H19120.7
C3—C2—C7111.4 (4)C21—C20—C19123.7 (5)
C1—C2—C7113.7 (4)C21—C20—Br1118.5 (4)
C3—C2—H2107.0C19—C20—Br1117.8 (4)
C1—C2—H2107.0C20—C21—O6120.2 (4)
C7—C2—H2107.0C20—C21—C22118.3 (4)
C4—C3—C2112.2 (4)O6—C21—C22121.5 (4)
C4—C3—H3A109.2C17—C22—C23117.1 (4)
C2—C3—H3A109.2C17—C22—C21118.6 (4)
C4—C3—H3B109.2C23—C22—C21124.3 (4)
C2—C3—H3B109.2C14—C23—O4117.4 (4)
H3A—C3—H3B107.9C14—C23—C22122.6 (4)
O3—C4—C5112.1 (4)O4—C23—C22119.8 (4)
O3—C4—C3106.2 (4)O5—C24—O4123.5 (5)
C5—C4—C3110.2 (4)O5—C24—C25127.5 (6)
O3—C4—H4109.4O4—C24—C25108.9 (5)
C5—C4—H4109.4C24—C25—H25A109.5
C3—C4—H4109.4C24—C25—H25B109.5
O1—C5—C4109.2 (4)H25A—C25—H25B109.5
O1—C5—C6114.0 (5)C24—C25—H25C109.5
C4—C5—C6113.0 (5)H25A—C25—H25C109.5
O1—C5—H5106.7H25B—C25—H25C109.5
C4—C5—H5106.7O6—C26—H26A109.5
C6—C5—H5106.7O6—C26—H26B109.5
O2—C6—C5113.9 (4)H26A—C26—H26B109.5
O2—C6—H6A108.8O6—C26—H26C109.5
C5—C6—H6A108.8H26A—C26—H26C109.5
O2—C6—H6B108.8H26B—C26—H26C109.5
C5—C6—H6B108.8O7—C27—H27A109.5
H6A—C6—H6B107.7O7—C27—H27B109.5
O2—C7—C8108.0 (5)H27A—C27—H27B109.5
O2—C7—C2112.3 (4)O7—C27—H27C109.5
C8—C7—C2111.2 (4)H27A—C27—H27C109.5
O2—C7—H7108.4H27B—C27—H27C109.5
C8—C7—H7108.4O3—C28—C29108.9 (5)
C2—C7—H7108.4O3—C28—H28A109.9
C13—C8—C9117.2 (6)C29—C28—H28A109.9
C13—C8—C7121.0 (6)O3—C28—H28B109.9
C9—C8—C7121.7 (5)C29—C28—H28B109.9
C8—C9—C10120.8 (7)H28A—C28—H28B108.3
C8—C9—H9119.6C34—C29—C30118.9 (5)
C10—C9—H9119.6C34—C29—C28120.7 (6)
C11—C10—C9119.8 (8)C30—C29—C28120.4 (6)
C11—C10—H10120.1C29—C30—C31120.6 (7)
C9—C10—H10120.1C29—C30—H30119.7
C12—C11—C10119.4 (8)C31—C30—H30119.7
C12—C11—H11120.3C32—C31—C30119.4 (7)
C10—C11—H11120.3C32—C31—H31120.3
C13—C12—C11120.4 (7)C30—C31—H31120.3
C13—C12—H12119.8C33—C32—C31120.7 (6)
C11—C12—H12119.8C33—C32—H32119.6
C12—C13—C8122.3 (8)C31—C32—H32119.6
C12—C13—H13118.8C32—C33—C34120.6 (7)
C8—C13—H13118.8C32—C33—H33119.7
C23—C14—C15118.7 (4)C34—C33—H33119.7
C23—C14—C1119.7 (4)C29—C34—C33119.6 (7)
C15—C14—C1121.5 (4)C29—C34—H34120.2
C16—C15—C14121.1 (5)C33—C34—H34120.2
C16—C15—H15119.5
C5—O1—C1—C14143.3 (4)C27—O7—C18—C193.8 (9)
C5—O1—C1—C220.0 (5)C27—O7—C18—C17175.1 (6)
O1—C1—C2—C340.0 (5)C22—C17—C18—O7179.5 (5)
C14—C1—C2—C381.1 (5)C16—C17—C18—O71.0 (8)
O1—C1—C2—C786.0 (5)C22—C17—C18—C190.5 (8)
C14—C1—C2—C7152.8 (4)C16—C17—C18—C19179.9 (6)
C1—C2—C3—C455.2 (5)O7—C18—C19—C20178.0 (5)
C7—C2—C3—C472.1 (5)C17—C18—C19—C203.2 (9)
C28—O3—C4—C589.0 (6)C18—C19—C20—C212.5 (9)
C28—O3—C4—C3150.6 (5)C18—C19—C20—Br1175.8 (5)
C2—C3—C4—O3131.5 (4)C19—C20—C21—O6179.7 (5)
C2—C3—C4—C59.8 (6)Br1—C20—C21—O61.9 (6)
C1—O1—C5—C468.2 (5)C19—C20—C21—C220.8 (8)
C1—O1—C5—C659.2 (5)Br1—C20—C21—C22179.1 (3)
O3—C4—C5—O168.3 (5)C26—O6—C21—C2089.6 (6)
C3—C4—C5—O149.8 (5)C26—O6—C21—C2291.4 (5)
O3—C4—C5—C6163.7 (4)C16—C17—C22—C233.7 (7)
C3—C4—C5—C678.2 (5)C18—C17—C22—C23176.8 (5)
C7—O2—C6—C564.8 (7)C16—C17—C22—C21176.8 (5)
O1—C5—C6—O296.4 (6)C18—C17—C22—C212.8 (7)
C4—C5—C6—O229.1 (7)C20—C21—C22—C173.4 (7)
C6—O2—C7—C8174.7 (5)O6—C21—C22—C17177.7 (4)
C6—O2—C7—C251.8 (7)C20—C21—C22—C23176.1 (5)
C3—C2—C7—O245.3 (6)O6—C21—C22—C232.8 (7)
C1—C2—C7—O280.2 (6)C15—C14—C23—O4176.8 (4)
C3—C2—C7—C875.8 (5)C1—C14—C23—O46.1 (7)
C1—C2—C7—C8158.7 (5)C15—C14—C23—C222.2 (7)
O2—C7—C8—C13158.2 (5)C1—C14—C23—C22179.3 (4)
C2—C7—C8—C1378.2 (7)C24—O4—C23—C14111.8 (5)
O2—C7—C8—C924.4 (7)C24—O4—C23—C2273.5 (6)
C2—C7—C8—C999.2 (6)C17—C22—C23—C145.1 (7)
C13—C8—C9—C100.3 (8)C21—C22—C23—C14175.4 (4)
C7—C8—C9—C10177.8 (5)C17—C22—C23—O4179.5 (4)
C8—C9—C10—C111.6 (10)C21—C22—C23—O41.0 (7)
C9—C10—C11—C121.5 (10)C23—O4—C24—O56.5 (8)
C10—C11—C12—C130.1 (10)C23—O4—C24—C25174.1 (4)
C11—C12—C13—C81.2 (10)C4—O3—C28—C29163.7 (5)
C9—C8—C13—C121.1 (9)O3—C28—C29—C3469.1 (8)
C7—C8—C13—C12176.4 (6)O3—C28—C29—C30110.0 (7)
O1—C1—C14—C23151.4 (4)C34—C29—C30—C313.8 (10)
C2—C1—C14—C2385.1 (5)C28—C29—C30—C31177.0 (6)
O1—C1—C14—C1531.5 (6)C29—C30—C31—C321.7 (11)
C2—C1—C14—C1591.9 (5)C30—C31—C32—C330.6 (11)
C23—C14—C15—C162.2 (8)C31—C32—C33—C340.5 (12)
C1—C14—C15—C16174.9 (5)C30—C29—C34—C333.8 (10)
C14—C15—C16—C173.5 (9)C28—C29—C34—C33177.0 (6)
C15—C16—C17—C220.4 (8)C32—C33—C34—C291.7 (12)
C15—C16—C17—C18179.1 (5)

Experimental details

Crystal data
Chemical formulaC34H33BrO7
Mr633.51
Crystal system, space groupOrthorhombic, P212121
Temperature (K)294
a, b, c (Å)19.515 (1), 23.667 (2), 6.541 (2)
V3)3021.0 (10)
Z4
Radiation typeCu Kα
µ (mm1)2.25
Crystal size (mm)0.55 × 0.13 × 0.08
Data collection
DiffractometerRigaku AFC7R
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.715, 0.835
No. of measured, independent and
observed [I > 2σ(I)] reflections
2962, 2962, 2068
Rint0.000
(sin θ/λ)max1)0.588
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.114, 1.02
No. of reflections2962
No. of parameters382
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.34
Absolute structureFlack (1983) and Bernardinelli & Flack(1985); No Friedel pairs
Absolute structure parameter0.06 (3)

Computer programs: MSC AFC Diffractometer Control (MSC, 1995), TEXSAN (MSC, 1992), SIR92 (Altomare, et al. 1993), SHELXL97 (Sheldrick, 1997), TEXSAN for Windows (MSC, 1997).

 

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