supplementary materials


xu5694 scheme

Acta Cryst. (2013). E69, o758    [ doi:10.1107/S160053681301026X ]

3-[(1-Bromonaphthalen-2-yl)methoxy]-5,5-dimethylcyclohex-2-enone

L.-L. Fang, N. Liu and X.-Y. Zhang

Abstract top

In the title compound, C19H19BrO2, the cyclohexenone ring adopts an envelope conformation with the C atom bearing the methyl substituents as the flap. In the crystal, weak [pi]-[pi] stacking is observed between parallel aromatic rings of adjacent molecules, the centroid-centroid distance being 3.694 (6) Å. The entire bromonaphthylmethyl unit is disordered over two orientations, with a site-occupancy ratio of 0.5214 (19):0.4786 (19).

Comment top

Cyclohex-2-enone derivatives display a wide range of biological activities (Aghil et al., 1992; Correcia et al., 2001). Moreover, they have been frequently used as precursors in the synthesis of heterocyclic compounds (Ghorab, et al., 2011). The title compound is the derivative of cyclohex-2-enones, and we report its crystal structure here.

In the title compound, C19H19BrO2, all the bond lengths and bond angles are within normal ranges. The cyclohexenone ring adopts an envelope conformation with the C atom bearing two methyl groups as the flap atom. All the atoms in the o-bromonaphthylmethyl group are disordered over two positions with site occupancy factors of 0.521 (2) and 0.479 (2).

In the crystal structure, weak π-π stacking is observed between parallel aromatic rings of adjacent molecules, the centrods distance being 3.694 (6) Å.

Related literature top

For the biological activity and applications of cyclohex-2-enone derivatives, see: Aghil et al. (1992); Correcia et al. (2001); Ghorab et al. (2011).

Experimental top

To a solution of 1-bromo-2-(bromomethyl)naphthalene (0.15 g, 0.5 mmol) and 5,5-dimethylcyclohexane-1,3-dione (0.14 g, 1.0 mmol) in DMF (3 ml) were added K2CO3 (0.21 g, 1.5 mmol) and CuI (0.01 g, 0.05 mmol). The mixture was stirred at 373 K until a complete conversion. It was cooled to room temperature and added with water, then extracted with ethyl ether (5 ml × 3). The combined organic phases were concentrated under vacuum. The crude product was purified by column chromatography eluting with ethyl acetate/hexane (10–20%) to give the title compound with the yield of 32% (0.057 g, 0.16 mmol). Single crystals, suitable for X-ray diffraction analysis, were obtained by slow evaporation of the solvents from a chloroform-ethyl acetate (1:1 v/v) solution of the title compound.

Refinement top

H atoms were positioned geometrically and refined using riding model with C—H = 0.93–0.97 Å, Uiso(H) = 1.2Ueq(C). The The bromonaphthalene moiety is disordered over two orientations, the site occupancies were refined to 0.5214 (19):0.4786 (19), the ADP of corresponding atoms in the disordered components were restrained as the same.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with the disorder atoms, with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Molecular structure of the title compound without the disorder atoms, with displacement ellipsoids drawn at the 30% probability level.
[Figure 3] Fig. 3. Crystal structure of the title compound with view along the a axis (disorder atoms have been omitted for clarity).
3-[(1-Bromonaphthalen-2-yl)methoxy]-5,5-dimethylcyclohex-2-enone top
Crystal data top
C19H19BrO2F(000) = 736
Mr = 359.25Dx = 1.439 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2538 reflections
a = 13.986 (3) Åθ = 2.5–20.6°
b = 9.9970 (18) ŵ = 2.48 mm1
c = 11.859 (2) ÅT = 296 K
β = 91.169 (2)°Block, colourless
V = 1657.8 (5) Å30.32 × 0.29 × 0.27 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
3075 independent reflections
Radiation source: fine-focus sealed tube1931 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.074
phi and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1616
Tmin = 0.504, Tmax = 0.554k = 1212
11934 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0635P)2 + 1.8223P]
where P = (Fo2 + 2Fc2)/3
3075 reflections(Δ/σ)max < 0.001
222 parametersΔρmax = 0.26 e Å3
72 restraintsΔρmin = 0.20 e Å3
Crystal data top
C19H19BrO2V = 1657.8 (5) Å3
Mr = 359.25Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.986 (3) ŵ = 2.48 mm1
b = 9.9970 (18) ÅT = 296 K
c = 11.859 (2) Å0.32 × 0.29 × 0.27 mm
β = 91.169 (2)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
3075 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1931 reflections with I > 2σ(I)
Tmin = 0.504, Tmax = 0.554Rint = 0.074
11934 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.061H-atom parameters constrained
wR(F2) = 0.199Δρmax = 0.26 e Å3
S = 1.07Δρmin = 0.20 e Å3
3075 reflectionsAbsolute structure: ?
222 parametersFlack parameter: ?
72 restraintsRogers parameter: ?
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*/UeqOcc. (<1)
Br10.93272 (9)0.21923 (16)0.49100 (14)0.0729 (5)0.5214 (19)
C90.8583 (5)0.0318 (10)0.6902 (8)0.0531 (17)0.5214 (19)
H9A0.83280.01220.61530.064*0.5214 (19)
H9B0.84640.04480.73810.064*0.5214 (19)
C101.1164 (5)0.0103 (9)0.7741 (7)0.0667 (19)0.5214 (19)
H101.15230.03160.83070.080*0.5214 (19)
C111.0182 (6)0.0061 (16)0.7684 (11)0.082 (4)0.5214 (19)
H110.98810.05990.82080.098*0.5214 (19)
C120.9649 (5)0.0574 (9)0.6848 (7)0.057 (2)0.5214 (19)
C131.0089 (4)0.1363 (8)0.6063 (6)0.0555 (17)0.5214 (19)
C141.1077 (4)0.1516 (9)0.6101 (7)0.068 (3)0.5214 (19)
C151.1529 (4)0.2292 (9)0.5302 (7)0.076 (3)0.5214 (19)
H151.11710.27070.47330.092*0.5214 (19)
C161.2513 (5)0.2448 (9)0.5352 (7)0.073 (3)0.5214 (19)
H161.28160.29680.48160.087*0.5214 (19)
C171.3047 (5)0.1829 (8)0.6201 (7)0.068 (3)0.5214 (19)
H171.37070.19340.62340.081*0.5214 (19)
C181.2595 (4)0.1054 (9)0.7000 (7)0.070 (2)0.5214 (19)
H181.29530.06380.75690.085*0.5214 (19)
C191.1611 (4)0.0897 (9)0.6950 (6)0.068 (3)0.5214 (19)
C9'0.8450 (6)0.0553 (11)0.6468 (9)0.0531 (17)0.4786 (19)
H9'10.80380.05950.58000.064*0.4786 (19)
H9'20.84580.03590.67480.064*0.4786 (19)
C10'1.0349 (5)0.2273 (10)0.4867 (7)0.0667 (19)0.4786 (19)
H10'1.03680.27770.42090.080*0.4786 (19)
C11'0.9485 (6)0.1796 (18)0.5240 (12)0.082 (4)0.4786 (19)
H11'0.89230.19960.48420.098*0.4786 (19)
C12'0.9454 (5)0.1022 (10)0.6205 (7)0.057 (2)0.4786 (19)
C13'1.0287 (5)0.0714 (9)0.6786 (7)0.0555 (17)0.4786 (19)
C14'1.1158 (4)0.1209 (10)0.6427 (7)0.068 (3)0.4786 (19)
C15'1.2003 (5)0.0901 (10)0.7016 (8)0.076 (3)0.4786 (19)
H15'1.19860.03690.76580.092*0.4786 (19)
C16'1.2875 (6)0.1393 (10)0.6641 (9)0.073 (3)0.4786 (19)
H16'1.34380.11880.70340.087*0.4786 (19)
C17'1.2901 (6)0.2191 (10)0.5678 (8)0.068 (3)0.4786 (19)
H17'1.34820.25190.54280.081*0.4786 (19)
C18'1.2056 (5)0.2498 (9)0.5089 (7)0.070 (2)0.4786 (19)
H18'1.20730.30310.44460.085*0.4786 (19)
C19'1.1184 (4)0.2007 (9)0.5463 (7)0.068 (3)0.4786 (19)
Br1'1.02132 (16)0.0384 (2)0.80852 (18)0.1011 (8)0.4786 (19)
C10.7221 (3)0.1315 (4)0.7734 (3)0.0451 (10)
C20.6685 (3)0.0219 (5)0.7571 (4)0.0515 (11)
H20.69150.04920.71490.062*
C30.5733 (3)0.0146 (5)0.8065 (4)0.0525 (11)
C40.5388 (3)0.1316 (5)0.8710 (4)0.0531 (11)
H4A0.49620.10010.92880.064*
H4B0.50200.18880.82040.064*
C50.6191 (3)0.2159 (4)0.9280 (3)0.0471 (10)
C60.6897 (3)0.2516 (4)0.8369 (4)0.0465 (10)
H6A0.65980.31430.78460.056*
H6B0.74480.29540.87140.056*
C70.6693 (4)0.1348 (6)1.0219 (4)0.0652 (14)
H7A0.71860.18821.05690.098*
H7B0.69720.05580.99020.098*
H7C0.62350.10951.07720.098*
C80.5763 (4)0.3438 (6)0.9770 (5)0.0684 (14)
H8A0.62630.39701.01070.103*
H8B0.53070.32071.03320.103*
H8C0.54500.39380.91780.103*
O10.8111 (2)0.1500 (3)0.7355 (3)0.0642 (10)
O20.5246 (3)0.0871 (4)0.7946 (3)0.0814 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0660 (7)0.0816 (11)0.0705 (9)0.0125 (6)0.0091 (5)0.0032 (7)
C90.0528 (19)0.0533 (19)0.053 (2)0.0011 (10)0.0026 (10)0.0008 (10)
C100.073 (5)0.065 (5)0.061 (4)0.008 (4)0.007 (4)0.009 (4)
C110.102 (8)0.075 (9)0.068 (9)0.010 (6)0.003 (6)0.013 (6)
C120.063 (5)0.051 (5)0.060 (6)0.007 (4)0.011 (5)0.017 (4)
C130.040 (4)0.062 (5)0.065 (5)0.001 (3)0.007 (4)0.006 (3)
C140.052 (3)0.067 (6)0.084 (7)0.003 (3)0.014 (4)0.024 (5)
C150.055 (7)0.079 (6)0.096 (7)0.010 (5)0.012 (5)0.004 (5)
C160.059 (5)0.063 (6)0.096 (7)0.013 (4)0.012 (4)0.004 (5)
C170.044 (4)0.067 (6)0.093 (9)0.002 (4)0.009 (5)0.008 (6)
C180.075 (7)0.060 (5)0.077 (6)0.001 (5)0.008 (5)0.001 (4)
C190.050 (5)0.059 (5)0.097 (7)0.004 (4)0.009 (5)0.021 (5)
C9'0.0528 (19)0.0533 (19)0.053 (2)0.0011 (10)0.0026 (10)0.0008 (10)
C10'0.073 (5)0.065 (5)0.061 (4)0.008 (4)0.007 (4)0.009 (4)
C11'0.102 (8)0.075 (9)0.068 (9)0.010 (6)0.003 (6)0.013 (6)
C12'0.063 (5)0.051 (5)0.060 (6)0.007 (4)0.011 (5)0.017 (4)
C13'0.040 (4)0.062 (5)0.065 (5)0.001 (3)0.007 (4)0.006 (3)
C14'0.052 (3)0.067 (6)0.084 (7)0.003 (3)0.014 (4)0.024 (5)
C15'0.055 (7)0.079 (6)0.096 (7)0.010 (5)0.012 (5)0.004 (5)
C16'0.059 (5)0.063 (6)0.096 (7)0.013 (4)0.012 (4)0.004 (5)
C17'0.044 (4)0.067 (6)0.093 (9)0.002 (4)0.009 (5)0.008 (6)
C18'0.075 (7)0.060 (5)0.077 (6)0.001 (5)0.008 (5)0.001 (4)
C19'0.050 (5)0.059 (5)0.097 (7)0.004 (4)0.009 (5)0.021 (5)
Br1'0.1561 (17)0.0705 (11)0.0769 (14)0.0061 (9)0.0059 (10)0.0235 (9)
C10.043 (2)0.050 (3)0.042 (2)0.0009 (19)0.0091 (18)0.0007 (19)
C20.051 (3)0.054 (3)0.050 (2)0.008 (2)0.008 (2)0.009 (2)
C30.053 (3)0.062 (3)0.042 (2)0.017 (2)0.001 (2)0.002 (2)
C40.042 (2)0.064 (3)0.053 (3)0.006 (2)0.006 (2)0.001 (2)
C50.041 (2)0.057 (3)0.043 (2)0.003 (2)0.0087 (18)0.001 (2)
C60.045 (2)0.051 (3)0.044 (2)0.0027 (19)0.0065 (18)0.0026 (19)
C70.072 (3)0.087 (4)0.037 (2)0.014 (3)0.001 (2)0.010 (2)
C80.063 (3)0.073 (3)0.070 (3)0.004 (3)0.015 (3)0.017 (3)
O10.0533 (19)0.059 (2)0.081 (2)0.0126 (15)0.0272 (17)0.0207 (18)
O20.069 (2)0.083 (3)0.093 (3)0.035 (2)0.018 (2)0.018 (2)
Geometric parameters (Å, º) top
Br1—C131.907 (6)C13'—Br1'1.897 (7)
C9—O11.461 (10)C14'—C15'1.395 (5)
C9—C121.515 (8)C14'—C19'1.395 (5)
C9—H9A0.9700C15'—C16'1.395 (5)
C9—H9B0.9700C15'—H15'0.9300
C10—C111.383 (6)C16'—C17'1.395 (5)
C10—C191.387 (6)C16'—H16'0.9300
C10—H100.9300C17'—C18'1.395 (5)
C11—C121.382 (6)C17'—H17'0.9300
C11—H110.9300C18'—C19'1.395 (5)
C12—C131.376 (6)C18'—H18'0.9300
C13—C141.390 (6)C1—C21.339 (6)
C14—C191.386 (5)C1—O11.345 (5)
C14—C151.386 (5)C1—C61.493 (6)
C15—C161.386 (5)C2—C31.467 (6)
C15—H150.9300C2—H20.9300
C16—C171.386 (5)C3—O21.231 (6)
C16—H160.9300C3—C41.483 (7)
C17—C181.386 (5)C4—C51.548 (6)
C17—H170.9300C4—H4A0.9700
C18—C191.386 (5)C4—H4B0.9700
C18—H180.9300C5—C61.520 (6)
C9'—O11.499 (11)C5—C81.531 (7)
C9'—C12'1.519 (9)C5—C71.536 (6)
C9'—H9'10.9700C6—H6A0.9700
C9'—H9'20.9700C6—H6B0.9700
C10'—C19'1.379 (7)C7—H7A0.9600
C10'—C11'1.380 (6)C7—H7B0.9600
C10'—H10'0.9300C7—H7C0.9600
C11'—C12'1.383 (6)C8—H8A0.9600
C11'—H11'0.9300C8—H8B0.9600
C12'—C13'1.377 (6)C8—H8C0.9600
C13'—C14'1.389 (7)
O1—C9—C12109.3 (7)C14'—C15'—C16'120.0
O1—C9—H9A109.8C14'—C15'—H15'120.0
C12—C9—H9A109.8C16'—C15'—H15'120.0
O1—C9—H9B109.8C15'—C16'—C17'120.0
C12—C9—H9B109.8C15'—C16'—H16'120.0
H9A—C9—H9B108.3C17'—C16'—H16'120.0
C11—C10—C19119.7 (4)C18'—C17'—C16'120.0
C11—C10—H10120.2C18'—C17'—H17'120.0
C19—C10—H10120.2C16'—C17'—H17'120.0
C12—C11—C10120.1 (4)C17'—C18'—C19'120.0
C12—C11—H11120.0C17'—C18'—H18'120.0
C10—C11—H11120.0C19'—C18'—H18'120.0
C13—C12—C11120.4 (4)C10'—C19'—C18'120.4 (4)
C13—C12—C9125.5 (6)C10'—C19'—C14'119.6 (4)
C11—C12—C9114.2 (6)C18'—C19'—C14'120.0
C12—C13—C14120.0 (4)C2—C1—O1125.7 (4)
C12—C13—Br1118.9 (4)C2—C1—C6123.7 (4)
C14—C13—Br1121.1 (4)O1—C1—C6110.6 (4)
C19—C14—C15120.0C1—C2—C3119.5 (4)
C19—C14—C13119.6 (3)C1—C2—H2120.2
C15—C14—C13120.4 (3)C3—C2—H2120.2
C16—C15—C14120.0O2—C3—C2120.0 (4)
C16—C15—H15120.0O2—C3—C4121.7 (4)
C14—C15—H15120.0C2—C3—C4118.3 (4)
C17—C16—C15120.0C3—C4—C5114.4 (4)
C17—C16—H16120.0C3—C4—H4A108.7
C15—C16—H16120.0C5—C4—H4A108.7
C16—C17—C18120.0C3—C4—H4B108.7
C16—C17—H17120.0C5—C4—H4B108.7
C18—C17—H17120.0H4A—C4—H4B107.6
C17—C18—C19120.0C6—C5—C8109.8 (4)
C17—C18—H18120.0C6—C5—C7110.2 (4)
C19—C18—H18120.0C8—C5—C7110.0 (4)
C14—C19—C18120.0C6—C5—C4107.1 (3)
C14—C19—C10120.2 (3)C8—C5—C4109.5 (4)
C18—C19—C10119.8 (3)C7—C5—C4110.2 (4)
O1—C9'—C12'104.8 (7)C1—C6—C5112.2 (3)
O1—C9'—H9'1110.8C1—C6—H6A109.2
C12'—C9'—H9'1110.8C5—C6—H6A109.2
O1—C9'—H9'2110.8C1—C6—H6B109.2
C12'—C9'—H9'2110.8C5—C6—H6B109.2
H9'1—C9'—H9'2108.9H6A—C6—H6B107.9
C19'—C10'—C11'120.5 (4)C5—C7—H7A109.5
C19'—C10'—H10'119.8C5—C7—H7B109.5
C11'—C10'—H10'119.8H7A—C7—H7B109.5
C10'—C11'—C12'120.1 (4)C5—C7—H7C109.5
C10'—C11'—H11'120.0H7A—C7—H7C109.5
C12'—C11'—H11'120.0H7B—C7—H7C109.5
C13'—C12'—C11'119.9 (4)C5—C8—H8A109.5
C13'—C12'—C9'127.3 (7)C5—C8—H8B109.5
C11'—C12'—C9'112.8 (7)H8A—C8—H8B109.5
C12'—C13'—C14'120.4 (4)C5—C8—H8C109.5
C12'—C13'—Br1'118.4 (4)H8A—C8—H8C109.5
C14'—C13'—Br1'121.2 (4)H8B—C8—H8C109.5
C13'—C14'—C15'120.5 (4)C1—O1—C9116.1 (4)
C13'—C14'—C19'119.5 (4)C1—O1—C9'117.1 (4)
C15'—C14'—C19'120.0C9—O1—C9'23.1 (5)
C19—C10—C11—C121 (2)C12'—C13'—C14'—C19'0.8 (14)
C10—C11—C12—C131 (2)Br1'—C13'—C14'—C19'179.6 (6)
C10—C11—C12—C9179.1 (13)C13'—C14'—C15'—C16'179.4 (11)
O1—C9—C12—C1375.3 (11)C19'—C14'—C15'—C16'0.0
O1—C9—C12—C11104.4 (12)C14'—C15'—C16'—C17'0.0
C11—C12—C13—C140.6 (17)C15'—C16'—C17'—C18'0.0
C9—C12—C13—C14179.8 (9)C16'—C17'—C18'—C19'0.0
C11—C12—C13—Br1178.9 (11)C11'—C10'—C19'—C18'179.5 (12)
C9—C12—C13—Br11.5 (13)C11'—C10'—C19'—C14'2.4 (17)
C12—C13—C14—C191.6 (12)C17'—C18'—C19'—C10'178.1 (10)
Br1—C13—C14—C19179.8 (5)C17'—C18'—C19'—C14'0.0
C12—C13—C14—C15178.9 (7)C13'—C14'—C19'—C10'1.3 (11)
Br1—C13—C14—C150.7 (11)C15'—C14'—C19'—C10'178.1 (10)
C19—C14—C15—C160.0C13'—C14'—C19'—C18'179.4 (11)
C13—C14—C15—C16179.5 (10)C15'—C14'—C19'—C18'0.0
C14—C15—C16—C170.0O1—C1—C2—C3178.3 (4)
C15—C16—C17—C180.0C6—C1—C2—C32.0 (7)
C16—C17—C18—C190.0C1—C2—C3—O2178.0 (5)
C15—C14—C19—C180.0C1—C2—C3—C41.4 (7)
C13—C14—C19—C18179.5 (10)O2—C3—C4—C5151.0 (4)
C15—C14—C19—C10179.0 (10)C2—C3—C4—C528.4 (6)
C13—C14—C19—C101.5 (10)C3—C4—C5—C652.9 (5)
C17—C18—C19—C140.0C3—C4—C5—C8171.8 (4)
C17—C18—C19—C10179.0 (9)C3—C4—C5—C767.0 (5)
C11—C10—C19—C140.4 (15)C2—C1—C6—C529.6 (6)
C11—C10—C19—C18179.4 (11)O1—C1—C6—C5150.7 (4)
C19'—C10'—C11'—C12'1 (2)C8—C5—C6—C1170.9 (4)
C10'—C11'—C12'—C13'1 (2)C7—C5—C6—C167.8 (5)
C10'—C11'—C12'—C9'178.3 (14)C4—C5—C6—C152.1 (5)
O1—C9'—C12'—C13'83.4 (12)C2—C1—O1—C911.2 (7)
O1—C9'—C12'—C11'99.3 (13)C6—C1—O1—C9169.1 (5)
C11'—C12'—C13'—C14'1.8 (18)C2—C1—O1—C9'14.7 (8)
C9'—C12'—C13'—C14'178.9 (10)C6—C1—O1—C9'165.1 (6)
C11'—C12'—C13'—Br1'178.6 (12)C12—C9—O1—C1162.9 (5)
C9'—C12'—C13'—Br1'1.5 (15)C12—C9—O1—C9'98.9 (13)
C12'—C13'—C14'—C15'179.8 (8)C12'—C9'—O1—C1179.2 (6)
Br1'—C13'—C14'—C15'0.2 (12)C12'—C9'—O1—C987.4 (13)
Acknowledgements top

This work was supported by the National Natural Science Foundation of China (No. 21172057).

references
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