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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1642.
Published online 2008 July 31. doi:  10.1107/S1600536808020333
PMCID: PMC2962195

3,3′-Dibromo-5,5′-bis­[(S)-l-menth­yloxy]-4,4′-(hexane-1,6-diyldiimino)difuran-2(5H)-one

Abstract

The title compound, C34H54Br2N2O6, was obtained by the Michael addition–elimination reaction of (5S)-5-(l-menthyl­oxy)-3,4-dibromo­furan-2(5H)-one with 1,6-hexa­nediamine in the presence of triethyl­amine. The crystal structure contains two chiral five-membered furan­one rings, in twist and envelope conformations, and two six-membered cyclo­hexane rings in chair conformations.

Related literature

For general background, see: Boukouvalas et al. (2007 [triangle]); Carter et al. (2002 [triangle]); Feringa & de Lange (1988 [triangle]); Pal et al. (2003 [triangle]).

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Object name is e-64-o1642-scheme1.jpg

Experimental

Crystal data

  • C34H54Br2N2O6
  • M r = 746.61
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1642-efi1.jpg
  • a = 8.2302 (2) Å
  • b = 9.1319 (2) Å
  • c = 12.7193 (3) Å
  • α = 105.0370 (10)°
  • β = 93.214 (2)°
  • γ = 100.499 (2)°
  • V = 902.37 (4) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 2.29 mm−1
  • T = 298 (2) K
  • 0.28 × 0.25 × 0.21 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.567, T max = 0.645
  • 11045 measured reflections
  • 5935 independent reflections
  • 4414 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.090
  • S = 0.97
  • 5935 reflections
  • 403 parameters
  • 3 restraints
  • H-atom parameters constrained
  • Δρmax = 0.50 e Å−3
  • Δρmin = −0.25 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2587 Friedel pairs
  • Flack parameter: 0.001 (8)

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020333/kp2170sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020333/kp2170Isup2.hkl

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

Acknowledgments

The work was supported by the National Natural Science Foundation of China (No. 20772035 and No. 20772037) and the NSF of Guangdong Province, China (No. 5300082 and No. 06025033).

supplementary crystallographic information

Comment

A chiral 2(5H)-furanone moiety, a frequently found substructure in natural products, have received considerable attention due to the significant biological activities, such as antifungal, antibacterial, and anti-inflammatory (Pal et al.; 2003). It is also an important synthetic intermediates (Feringa & de Lange, 1988), and widely used in asymmetry reactions (Carter et al., 2002; Boukouvalas et al., 2007). Here we report the crystal structure of the title compound, N,N'-bis-[3-bromo-5-S-(l-menthloxy)-2(5H)-4-furanon-yl]-hexane- 1,6-diamine (I), namely C34N2H54Br2O6(Fig. 1), obtained via Michael addition-elimination reaction. The molecule of (I) has eight chiral centres (C4(S),C7(R),C10(R),C11(S),C24(S),C25(R),C27(R),C31(S)). The two chiral five-membered furanone rings are in a twisted conformation (C11/C14) and an envelope (C24) conformation whereas two six-membered cyclohexane rings are in the chair conformation.The bond lengths and angles in the title compound are in good agreement with expected values.

Experimental

The title compound (I) was prepared by reaction of 5-S-(l-menthloxy)-3,4-dibromo-2(5H)-furanone with the 1,6-hexanediamine in DMF with existence of triethylamine under N2 atmosphere. After stirring for 4 h at room temperature, the resulting solid was isolated by silica gel column chromatography with gradient mixtures of petroleum ether and ethyl acetate. Colourless crystals of (I) were obtained by slow evaporation of a solution in acetone (yield: 78%). EIS-MS (m/z): 769.75 [M+Na]+ (95%). [α]D25:+52.42°.

Refinement

The structure was solved using direct methods followed by Fourier synthesis. Non-H atoms were refined anisotropically. All of H atoms were placed in idealized positions, forced to ride on the atom to which they are bonded.

Figures

Fig. 1.
The molecular structure of the title molecule. The atom-numbering scheme is shown at the 50% probability level.

Crystal data

C34H54Br2N2O6Z = 1
Mr = 746.61F000 = 390
Triclinic, P1Dx = 1.374 Mg m3
Hall symbol: P 1Mo Kα radiation λ = 0.71073 Å
a = 8.2302 (2) ÅCell parameters from 2819 reflections
b = 9.1319 (2) Åθ = 2.0–23.7º
c = 12.7193 (3) ŵ = 2.29 mm1
α = 105.0370 (10)ºT = 298 (2) K
β = 93.214 (2)ºBlock, colourless
γ = 100.499 (2)º0.28 × 0.25 × 0.21 mm
V = 902.37 (4) Å3

Data collection

Bruker SMART CCD area-detector diffractometer5935 independent reflections
Radiation source: fine-focus sealed tube4414 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.032
T = 298(2) Kθmax = 25.5º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.567, Tmax = 0.645k = −11→11
11045 measured reflectionsl = −15→15

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039  w = 1/[σ2(Fo2) + (0.0205P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.090(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.50 e Å3
5935 reflectionsΔρmin = −0.25 e Å3
403 parametersExtinction correction: none
3 restraintsAbsolute structure: Flack (1983), 2587 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.001 (8)
Secondary atom site location: difference Fourier map

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br10.81496 (5)0.16597 (5)0.19540 (3)0.0760 (2)
Br2−0.34832 (6)−0.19512 (5)−0.08054 (3)0.0817 (2)
O10.6471 (4)0.2464 (3)0.5844 (3)0.0488 (9)
O20.9096 (4)0.2804 (4)0.5257 (2)0.0628 (8)
O31.0762 (5)0.1927 (5)0.4010 (4)0.0813 (12)
O4−0.1811 (4)−0.2781 (3)−0.4703 (3)0.0416 (8)
O5−0.3972 (4)−0.1676 (3)−0.3926 (2)0.0535 (7)
O6−0.5937 (5)−0.1698 (4)−0.2778 (3)0.0754 (11)
N10.5276 (5)0.2891 (4)0.3820 (3)0.0567 (10)
H10.47190.31690.43630.068*
N2−0.0273 (5)−0.2212 (4)−0.2574 (3)0.0583 (10)
H2A0.0307−0.2360−0.31200.070*
C10.3035 (7)0.4220 (6)0.6869 (6)0.0815 (19)
H1A0.29560.46540.76330.122*
H1B0.20160.41910.64510.122*
H1C0.39380.48480.66400.122*
C20.3345 (6)0.2579 (5)0.6683 (4)0.0491 (13)
H20.34830.21900.59070.059*
C30.1811 (6)0.1539 (6)0.6920 (4)0.0591 (13)
H3A0.20410.05330.68770.089*
H3B0.08920.14440.63900.089*
H3C0.15360.19870.76410.089*
C40.4919 (6)0.2472 (5)0.7355 (4)0.0421 (11)
H40.49360.13670.72070.051*
C50.4948 (7)0.3092 (6)0.8604 (4)0.0534 (13)
H5A0.48830.41770.87830.064*
H5B0.39760.25370.88370.064*
C60.6485 (9)0.2925 (7)0.9225 (5)0.0574 (13)
H6A0.64510.33641.00030.069*
H6B0.64970.18340.91030.069*
C70.8034 (5)0.3711 (5)0.8886 (3)0.0500 (10)
H70.80110.48160.90460.060*
C80.9614 (8)0.3565 (7)0.9516 (5)0.0807 (19)
H8A0.95730.39711.02880.121*
H8B1.05700.41370.92960.121*
H8C0.96880.24940.93590.121*
C90.8047 (6)0.3094 (5)0.7646 (4)0.0477 (11)
H9A0.90170.36680.74240.057*
H9B0.81410.20160.74730.057*
C100.6510 (5)0.3221 (5)0.6998 (3)0.0412 (9)
H100.65040.43190.70900.049*
C110.7495 (5)0.3225 (5)0.5261 (3)0.0450 (9)
H110.76210.43470.55580.054*
C120.9450 (7)0.2278 (6)0.4195 (4)0.0560 (12)
C130.8051 (7)0.2291 (5)0.3483 (4)0.0527 (12)
C140.6817 (6)0.2727 (5)0.4052 (3)0.0434 (10)
C150.4440 (7)0.2641 (5)0.2717 (4)0.0557 (13)
H15A0.52500.30060.22680.067*
H15B0.36000.32690.27710.067*
C160.3626 (6)0.0992 (5)0.2142 (4)0.0523 (12)
H16A0.27600.06280.25550.063*
H16B0.44420.03400.20970.063*
C170.2882 (7)0.0881 (6)0.1000 (4)0.0598 (14)
H17A0.20920.15600.10620.072*
H17B0.37640.12670.06050.072*
C180.2019 (7)−0.0710 (5)0.0330 (4)0.0575 (13)
H18A0.1150−0.11180.07230.069*
H18B0.2811−0.13880.02320.069*
C190.1264 (8)−0.0707 (6)−0.0781 (4)0.0631 (14)
H19A0.0414−0.0088−0.06770.076*
H19B0.2120−0.0212−0.11420.076*
C200.0509 (7)−0.2275 (6)−0.1513 (4)0.0580 (13)
H20A0.1363−0.2885−0.16480.070*
H20B−0.0324−0.2790−0.11470.070*
C21−0.1792 (6)−0.1947 (5)−0.2765 (3)0.0464 (10)
C22−0.3149 (6)−0.1883 (5)−0.2240 (4)0.0501 (12)
C23−0.4531 (7)−0.1733 (5)−0.2942 (4)0.0543 (12)
C24−0.2224 (5)−0.1659 (4)−0.3874 (3)0.0438 (9)
H24−0.1615−0.0637−0.38860.053*
C25−0.1587 (5)−0.2389 (5)−0.5739 (3)0.0422 (9)
H25−0.1167−0.1271−0.55830.051*
C26−0.3272 (6)−0.2820 (5)−0.6436 (4)0.0479 (12)
H26A−0.3776−0.3886−0.64870.057*
H26B−0.3998−0.2169−0.60740.057*
C27−0.3136 (6)−0.2637 (5)−0.7591 (3)0.0540 (11)
H27−0.2764−0.1533−0.75310.065*
C28−0.4850 (7)−0.3194 (8)−0.8265 (4)0.0748 (17)
H28A−0.4754−0.3079−0.89890.112*
H28B−0.5608−0.2588−0.79180.112*
H28C−0.5258−0.4265−0.83080.112*
C29−0.1843 (9)−0.3484 (8)−0.8117 (5)0.0659 (15)
H29A−0.1695−0.3286−0.88230.079*
H29B−0.2236−0.4589−0.82420.079*
C30−0.0177 (7)−0.2986 (7)−0.7412 (4)0.0651 (15)
H30A0.0262−0.1900−0.73410.078*
H30B0.0600−0.3576−0.77730.078*
C31−0.0318 (6)−0.3223 (5)−0.6278 (4)0.0465 (12)
H31−0.0756−0.4330−0.63870.056*
C320.1388 (6)−0.2838 (6)−0.5590 (5)0.0545 (13)
H320.1153−0.2782−0.48350.065*
C330.2355 (8)−0.4138 (7)−0.5922 (6)0.0851 (18)
H33A0.2692−0.4188−0.66390.128*
H33B0.1659−0.5107−0.59300.128*
H33C0.3320−0.3933−0.54060.128*
C340.2432 (7)−0.1293 (6)−0.5557 (5)0.0677 (15)
H34A0.2826−0.1333−0.62580.102*
H34B0.3362−0.1044−0.50070.102*
H34C0.1774−0.0512−0.53840.102*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.1001 (5)0.0902 (4)0.0445 (3)0.0276 (3)0.0298 (3)0.0200 (3)
Br20.1127 (5)0.0972 (4)0.0483 (4)0.0293 (4)0.0368 (4)0.0320 (3)
O10.058 (2)0.0498 (18)0.0312 (18)0.0000 (16)0.0030 (17)0.0068 (14)
O20.0488 (19)0.100 (2)0.0454 (17)0.0176 (17)0.0113 (14)0.0272 (16)
O30.064 (3)0.117 (3)0.085 (3)0.040 (2)0.030 (2)0.047 (2)
O40.0459 (19)0.0449 (17)0.0359 (19)0.0083 (14)0.0140 (16)0.0129 (14)
O50.0533 (19)0.0693 (19)0.0458 (16)0.0212 (15)0.0161 (14)0.0217 (14)
O60.075 (3)0.086 (3)0.085 (3)0.037 (2)0.042 (2)0.037 (2)
N10.063 (3)0.070 (3)0.0352 (19)0.021 (2)0.0022 (18)0.0063 (18)
N20.057 (3)0.077 (3)0.0358 (19)0.003 (2)0.0035 (18)0.0146 (18)
C10.062 (4)0.066 (3)0.119 (5)0.013 (3)−0.009 (3)0.034 (3)
C20.052 (3)0.047 (3)0.045 (3)0.005 (2)0.006 (3)0.011 (2)
C30.051 (3)0.062 (3)0.067 (3)0.011 (2)0.014 (2)0.021 (2)
C40.044 (3)0.044 (2)0.038 (2)0.0074 (19)0.006 (2)0.0116 (19)
C50.055 (3)0.064 (3)0.037 (3)0.002 (2)0.012 (2)0.011 (2)
C60.073 (4)0.062 (3)0.036 (3)0.015 (3)0.003 (3)0.012 (2)
C70.057 (3)0.054 (3)0.037 (2)0.015 (2)0.002 (2)0.0076 (18)
C80.070 (4)0.113 (5)0.055 (4)0.038 (3)−0.012 (3)0.007 (3)
C90.037 (3)0.061 (3)0.043 (3)0.010 (2)0.008 (2)0.011 (2)
C100.045 (3)0.041 (2)0.0334 (19)0.0039 (18)0.0076 (18)0.0065 (16)
C110.045 (3)0.050 (2)0.041 (2)0.0070 (19)0.0072 (19)0.0140 (18)
C120.056 (3)0.068 (3)0.055 (3)0.022 (3)0.024 (3)0.028 (2)
C130.063 (3)0.059 (3)0.042 (2)0.015 (2)0.013 (2)0.021 (2)
C140.054 (3)0.041 (2)0.036 (2)0.008 (2)0.007 (2)0.0124 (17)
C150.066 (3)0.062 (3)0.039 (3)0.019 (2)−0.003 (2)0.011 (2)
C160.054 (3)0.068 (3)0.037 (3)0.013 (2)0.005 (2)0.019 (2)
C170.053 (3)0.072 (3)0.050 (3)0.001 (2)−0.002 (2)0.018 (2)
C180.070 (4)0.068 (3)0.036 (3)0.012 (3)0.004 (3)0.020 (2)
C190.078 (4)0.063 (3)0.046 (3)0.006 (3)−0.003 (3)0.019 (2)
C200.064 (3)0.064 (3)0.047 (3)0.009 (2)0.001 (2)0.021 (2)
C210.052 (3)0.046 (2)0.036 (2)−0.001 (2)0.004 (2)0.0097 (18)
C220.064 (3)0.053 (3)0.034 (2)0.010 (2)0.018 (2)0.0109 (19)
C230.072 (4)0.043 (3)0.053 (3)0.017 (2)0.025 (3)0.015 (2)
C240.050 (3)0.044 (2)0.034 (2)0.0030 (18)0.0106 (18)0.0090 (16)
C250.047 (3)0.049 (2)0.033 (2)0.0101 (19)0.0094 (18)0.0146 (17)
C260.053 (3)0.056 (3)0.036 (2)0.012 (2)0.011 (2)0.0127 (19)
C270.059 (3)0.067 (3)0.037 (2)0.009 (2)0.009 (2)0.019 (2)
C280.068 (4)0.124 (5)0.037 (3)0.022 (3)0.005 (3)0.029 (3)
C290.065 (4)0.091 (4)0.037 (3)0.007 (3)0.017 (3)0.014 (3)
C300.061 (4)0.087 (4)0.042 (3)0.012 (3)0.016 (3)0.010 (2)
C310.042 (3)0.047 (3)0.050 (3)0.007 (2)0.015 (2)0.011 (2)
C320.044 (3)0.071 (3)0.057 (3)0.017 (2)0.015 (3)0.028 (3)
C330.070 (4)0.072 (4)0.125 (5)0.021 (3)0.020 (4)0.043 (3)
C340.056 (3)0.064 (3)0.074 (4)0.015 (2)−0.009 (3)0.005 (3)

Geometric parameters (Å, °)

Br1—C131.890 (5)C15—C161.502 (7)
Br2—C221.876 (5)C15—H15A0.9700
O1—C111.366 (5)C15—H15B0.9700
O1—C101.448 (5)C16—C171.516 (7)
O2—C121.378 (6)C16—H16A0.9700
O2—C111.438 (5)C16—H16B0.9700
O3—C121.200 (6)C17—C181.502 (6)
O4—C241.373 (5)C17—H17A0.9700
O4—C251.464 (5)C17—H17B0.9700
O5—C231.368 (5)C18—C191.512 (6)
O5—C241.433 (5)C18—H18A0.9700
O6—C231.192 (6)C18—H18B0.9700
N1—C141.330 (5)C19—C201.491 (7)
N1—C151.471 (6)C19—H19A0.9700
N1—H10.8600C19—H19B0.9700
N2—C211.337 (6)C20—H20A0.9700
N2—C201.482 (6)C20—H20B0.9700
N2—H2A0.8600C21—C221.335 (7)
C1—C21.526 (7)C21—C241.535 (5)
C1—H1A0.9600C22—C231.454 (7)
C1—H1B0.9600C24—H240.9800
C1—H1C0.9600C25—C311.497 (6)
C2—C31.530 (7)C25—C261.532 (6)
C2—C41.544 (7)C25—H250.9800
C2—H20.9800C26—C271.529 (6)
C3—H3A0.9600C26—H26A0.9700
C3—H3B0.9600C26—H26B0.9700
C3—H3C0.9600C27—C291.513 (9)
C4—C101.513 (6)C27—C281.536 (7)
C4—C51.539 (7)C27—H270.9800
C4—H40.9800C28—H28A0.9600
C5—C61.506 (9)C28—H28B0.9600
C5—H5A0.9700C28—H28C0.9600
C5—H5B0.9700C29—C301.521 (9)
C6—C71.489 (8)C29—H29A0.9700
C6—H6A0.9700C29—H29B0.9700
C6—H6B0.9700C30—C311.521 (7)
C7—C91.533 (6)C30—H30A0.9700
C7—C81.533 (7)C30—H30B0.9700
C7—H70.9800C31—C321.544 (7)
C8—H8A0.9600C31—H310.9800
C8—H8B0.9600C32—C341.502 (7)
C8—H8C0.9600C32—C331.530 (7)
C9—C101.509 (6)C32—H320.9800
C9—H9A0.9700C33—H33A0.9600
C9—H9B0.9700C33—H33B0.9600
C10—H100.9800C33—H33C0.9600
C11—C141.526 (5)C34—H34A0.9600
C11—H110.9800C34—H34B0.9600
C12—C131.429 (7)C34—H34C0.9600
C13—C141.339 (7)
C11—O1—C10116.8 (3)C18—C17—H17A108.3
C12—O2—C11109.9 (3)C16—C17—H17A108.3
C24—O4—C25116.0 (3)C18—C17—H17B108.3
C23—O5—C24109.9 (3)C16—C17—H17B108.3
C14—N1—C15125.9 (4)H17A—C17—H17B107.4
C14—N1—H1117.1C17—C18—C19112.2 (3)
C15—N1—H1117.1C17—C18—H18A109.2
C21—N2—C20126.3 (4)C19—C18—H18A109.2
C21—N2—H2A116.9C17—C18—H18B109.2
C20—N2—H2A116.9C19—C18—H18B109.2
C2—C1—H1A109.5H18A—C18—H18B107.9
C2—C1—H1B109.5C20—C19—C18114.4 (4)
H1A—C1—H1B109.5C20—C19—H19A108.7
C2—C1—H1C109.5C18—C19—H19A108.7
H1A—C1—H1C109.5C20—C19—H19B108.7
H1B—C1—H1C109.5C18—C19—H19B108.7
C1—C2—C3109.2 (5)H19A—C19—H19B107.6
C1—C2—C4114.2 (4)N2—C20—C19112.5 (4)
C3—C2—C4110.5 (4)N2—C20—H20A109.1
C1—C2—H2107.6C19—C20—H20A109.1
C3—C2—H2107.6N2—C20—H20B109.1
C4—C2—H2107.6C19—C20—H20B109.1
C2—C3—H3A109.5H20A—C20—H20B107.8
C2—C3—H3B109.5C22—C21—N2136.9 (4)
H3A—C3—H3B109.5C22—C21—C24106.2 (4)
C2—C3—H3C109.5N2—C21—C24116.9 (4)
H3A—C3—H3C109.5C21—C22—C23111.1 (4)
H3B—C3—H3C109.5C21—C22—Br2130.3 (4)
C10—C4—C5109.4 (4)C23—C22—Br2118.6 (4)
C10—C4—C2112.9 (4)O6—C23—O5121.9 (5)
C5—C4—C2114.8 (4)O6—C23—C22130.5 (5)
C10—C4—H4106.4O5—C23—C22107.5 (4)
C5—C4—H4106.4O4—C24—O5113.3 (3)
C2—C4—H4106.4O4—C24—C21109.9 (3)
C6—C5—C4112.9 (5)O5—C24—C21104.5 (3)
C6—C5—H5A109.0O4—C24—H24109.7
C4—C5—H5A109.0O5—C24—H24109.7
C6—C5—H5B109.0C21—C24—H24109.7
C4—C5—H5B109.0O4—C25—C31107.8 (3)
H5A—C5—H5B107.8O4—C25—C26109.0 (3)
C7—C6—C5112.1 (5)C31—C25—C26113.2 (4)
C7—C6—H6A109.2O4—C25—H25108.9
C5—C6—H6A109.2C31—C25—H25108.9
C7—C6—H6B109.2C26—C25—H25108.9
C5—C6—H6B109.2C27—C26—C25112.9 (4)
H6A—C6—H6B107.9C27—C26—H26A109.0
C6—C7—C9109.5 (4)C25—C26—H26A109.0
C6—C7—C8112.9 (4)C27—C26—H26B109.0
C9—C7—C8111.6 (4)C25—C26—H26B109.0
C6—C7—H7107.5H26A—C26—H26B107.8
C9—C7—H7107.5C29—C27—C26109.8 (4)
C8—C7—H7107.5C29—C27—C28112.7 (4)
C7—C8—H8A109.5C26—C27—C28109.9 (4)
C7—C8—H8B109.5C29—C27—H27108.1
H8A—C8—H8B109.5C26—C27—H27108.1
C7—C8—H8C109.5C28—C27—H27108.1
H8A—C8—H8C109.5C27—C28—H28A109.5
H8B—C8—H8C109.5C27—C28—H28B109.5
C10—C9—C7113.1 (4)H28A—C28—H28B109.5
C10—C9—H9A109.0C27—C28—H28C109.5
C7—C9—H9A109.0H28A—C28—H28C109.5
C10—C9—H9B109.0H28B—C28—H28C109.5
C7—C9—H9B109.0C27—C29—C30112.2 (5)
H9A—C9—H9B107.8C27—C29—H29A109.2
O1—C10—C9111.5 (4)C30—C29—H29A109.2
O1—C10—C4106.1 (3)C27—C29—H29B109.2
C9—C10—C4112.8 (3)C30—C29—H29B109.2
O1—C10—H10108.8H29A—C29—H29B107.9
C9—C10—H10108.8C29—C30—C31112.2 (5)
C4—C10—H10108.8C29—C30—H30A109.2
O1—C11—O2111.5 (3)C31—C30—H30A109.2
O1—C11—C14110.6 (3)C29—C30—H30B109.2
O2—C11—C14103.8 (3)C31—C30—H30B109.2
O1—C11—H11110.2H30A—C30—H30B107.9
O2—C11—H11110.2C25—C31—C30109.6 (4)
C14—C11—H11110.2C25—C31—C32114.7 (4)
O3—C12—O2120.6 (5)C30—C31—C32112.5 (4)
O3—C12—C13131.6 (5)C25—C31—H31106.5
O2—C12—C13107.7 (4)C30—C31—H31106.5
C14—C13—C12111.1 (4)C32—C31—H31106.5
C14—C13—Br1130.3 (4)C34—C32—C33111.5 (5)
C12—C13—Br1118.5 (4)C34—C32—C31114.3 (4)
N1—C14—C13136.4 (4)C33—C32—C31112.0 (5)
N1—C14—C11116.7 (4)C34—C32—H32106.1
C13—C14—C11106.8 (4)C33—C32—H32106.1
N1—C15—C16115.2 (4)C31—C32—H32106.1
N1—C15—H15A108.5C32—C33—H33A109.5
C16—C15—H15A108.5C32—C33—H33B109.5
N1—C15—H15B108.5H33A—C33—H33B109.5
C16—C15—H15B108.5C32—C33—H33C109.5
H15A—C15—H15B107.5H33A—C33—H33C109.5
C15—C16—C17110.0 (4)H33B—C33—H33C109.5
C15—C16—H16A109.7C32—C34—H34A109.5
C17—C16—H16A109.7C32—C34—H34B109.5
C15—C16—H16B109.7H34A—C34—H34B109.5
C17—C16—H16B109.7C32—C34—H34C109.5
H16A—C16—H16B108.2H34A—C34—H34C109.5
C18—C17—C16115.7 (4)H34B—C34—H34C109.5
C1—C2—C4—C10−67.7 (6)C17—C18—C19—C20175.3 (5)
C3—C2—C4—C10168.8 (4)C21—N2—C20—C19−82.3 (6)
C1—C2—C4—C558.7 (6)C18—C19—C20—N2177.8 (5)
C3—C2—C4—C5−64.9 (5)C20—N2—C21—C22−11.8 (8)
C10—C4—C5—C6−53.3 (5)C20—N2—C21—C24169.8 (4)
C2—C4—C5—C6178.5 (4)N2—C21—C22—C23−172.6 (5)
C4—C5—C6—C757.0 (6)C24—C21—C22—C235.8 (5)
C5—C6—C7—C9−55.4 (6)N2—C21—C22—Br27.6 (9)
C5—C6—C7—C8179.6 (5)C24—C21—C22—Br2−173.9 (3)
C6—C7—C9—C1054.3 (5)C24—O5—C23—O6177.1 (4)
C8—C7—C9—C10−179.9 (4)C24—O5—C23—C22−4.6 (4)
C11—O1—C10—C9−75.9 (5)C21—C22—C23—O6177.0 (5)
C11—O1—C10—C4160.9 (3)Br2—C22—C23—O6−3.2 (7)
C7—C9—C10—O1−173.2 (3)C21—C22—C23—O5−1.1 (5)
C7—C9—C10—C4−53.9 (5)Br2—C22—C23—O5178.7 (3)
C5—C4—C10—O1174.0 (4)C25—O4—C24—O584.4 (4)
C2—C4—C10—O1−56.8 (5)C25—O4—C24—C21−159.1 (3)
C5—C4—C10—C951.6 (5)C23—O5—C24—O4127.4 (3)
C2—C4—C10—C9−179.2 (4)C23—O5—C24—C217.8 (4)
C10—O1—C11—O290.3 (4)C22—C21—C24—O4−130.1 (4)
C10—O1—C11—C14−154.7 (3)N2—C21—C24—O448.7 (5)
C12—O2—C11—O1124.9 (4)C22—C21—C24—O5−8.3 (4)
C12—O2—C11—C145.8 (4)N2—C21—C24—O5170.5 (3)
C11—O2—C12—O3176.9 (5)C24—O4—C25—C31149.2 (3)
C11—O2—C12—C13−2.2 (5)C24—O4—C25—C26−87.5 (4)
O3—C12—C13—C14178.0 (6)O4—C25—C26—C27−173.0 (3)
O2—C12—C13—C14−3.0 (5)C31—C25—C26—C27−53.1 (5)
O3—C12—C13—Br10.0 (8)C25—C26—C27—C2951.6 (5)
O2—C12—C13—Br1179.0 (3)C25—C26—C27—C28176.1 (4)
C15—N1—C14—C13−2.3 (8)C26—C27—C29—C30−53.9 (6)
C15—N1—C14—C11173.3 (4)C28—C27—C29—C30−176.8 (5)
C12—C13—C14—N1−177.6 (5)C27—C29—C30—C3157.4 (7)
Br1—C13—C14—N10.1 (9)O4—C25—C31—C30174.1 (3)
C12—C13—C14—C116.5 (5)C26—C25—C31—C3053.4 (5)
Br1—C13—C14—C11−175.8 (3)O4—C25—C31—C32−58.3 (5)
O1—C11—C14—N155.9 (5)C26—C25—C31—C32−179.0 (4)
O2—C11—C14—N1175.7 (4)C29—C30—C31—C25−55.6 (6)
O1—C11—C14—C13−127.3 (4)C29—C30—C31—C32175.6 (5)
O2—C11—C14—C13−7.5 (4)C25—C31—C32—C34−76.0 (6)
C14—N1—C15—C1684.6 (6)C30—C31—C32—C3450.1 (6)
N1—C15—C16—C17−177.4 (4)C25—C31—C32—C33156.0 (5)
C15—C16—C17—C18−179.8 (4)C30—C31—C32—C33−77.9 (6)
C16—C17—C18—C19178.0 (6)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2170).

References

  • Boukouvalas, J., Cote, S. & Ndzi, B. (2007). Tetrahedron Lett.48, 105–107.
  • Bruker (1998). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Carter, N. B., Mabon, R., Richecoeur, A. M. E. & Sweeney, J. B. (2002). Tetrahedron, 58, 9117–9129.
  • Feringa, B. L. & de Lange, B. (1988). Tetrahedron Lett.29, 1303–1306.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Pal, M., Veeramaneni, V. R., Nagabelli, M., Kalleda, S. R., Misra, P., Casturi, S. R. & Yeleswarapu, K. R. (2003). Bioorg. Med. Chem. Lett.13, 1639–1643. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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