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

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

doi:10.1107/S160053681301026X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o758

https://doi.org/10.1107/S160053681301026X

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

Liang-Liang Fang,^a Nan Liu ^a and Xin-Ying Zhang ^a ^*

^aSchool of Chemistry and Chemical Engineering, Henan Normal University, Henan 453007, People's Republic of China
^*Correspondence e-mail: xinyingzhang@htu.cn

(Received 10 April 2013; accepted 15 April 2013; online 20 April 2013)

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 π–π 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).

Related literature

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

Crystal data

C₁₉H₁₉BrO₂
M_r = 359.25
Monoclinic, P 2₁ /c
a = 13.986 (3) Å
b = 9.9970 (18) Å
c = 11.859 (2) Å
β = 91.169 (2)°
V = 1657.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 2.48 mm⁻¹
T = 296 K
0.32 × 0.29 × 0.27 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.504, T_max = 0.554
11934 measured reflections
3075 independent reflections
1931 reflections with I > 2σ(I)
R_int = 0.074

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.199
S = 1.07
3075 reflections
222 parameters
72 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681301026X/xu5694sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681301026X/xu5694Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681301026X/xu5694Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S160053681301026X/xu5694Isup4.cml

checkCIF report

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.

Structure description top

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.

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

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

	Fig. 1. Molecular structure of the title compound with the disorder atoms, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Molecular structure of the title compound without the disorder atoms, with displacement ellipsoids drawn at the 30% probability level.
	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

C₁₉H₁₉BrO₂	F(000) = 736
M_r = 359.25	D_x = 1.439 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2538 reflections
a = 13.986 (3) Å	θ = 2.5–20.6°
b = 9.9970 (18) Å	µ = 2.48 mm⁻¹
c = 11.859 (2) Å	T = 296 K
β = 91.169 (2)°	Block, colourless
V = 1657.8 (5) Å³	0.32 × 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 tube	1931 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
phi and ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
T_min = 0.504, T_max = 0.554	k = −12→12
11934 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.199	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0635P)² + 1.8223P] where P = (F_o² + 2F_c²)/3
3075 reflections	(Δ/σ)_max < 0.001
222 parameters	Δρ_max = 0.26 e Å⁻³
72 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₉H₁₉BrO₂	V = 1657.8 (5) Å³
M_r = 359.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.986 (3) Å	µ = 2.48 mm⁻¹
b = 9.9970 (18) Å	T = 296 K
c = 11.859 (2) Å	0.32 × 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)
T_min = 0.504, T_max = 0.554	R_int = 0.074
11934 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	72 restraints
wR(F²) = 0.199	H-atom parameters constrained
S = 1.07	Δρ_max = 0.26 e Å⁻³
3075 reflections	Δρ_min = −0.20 e Å⁻³
222 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1	0.93272 (9)	0.21923 (16)	0.49100 (14)	0.0729 (5)	0.5214 (19)
C9	0.8583 (5)	0.0318 (10)	0.6902 (8)	0.0531 (17)	0.5214 (19)
H9A	0.8328	0.0122	0.6153	0.064*	0.5214 (19)
H9B	0.8464	−0.0448	0.7381	0.064*	0.5214 (19)
C10	1.1164 (5)	0.0103 (9)	0.7741 (7)	0.0667 (19)	0.5214 (19)
H10	1.1523	−0.0316	0.8307	0.080*	0.5214 (19)
C11	1.0182 (6)	−0.0061 (16)	0.7684 (11)	0.082 (4)	0.5214 (19)
H11	0.9881	−0.0599	0.8208	0.098*	0.5214 (19)
C12	0.9649 (5)	0.0574 (9)	0.6848 (7)	0.057 (2)	0.5214 (19)
C13	1.0089 (4)	0.1363 (8)	0.6063 (6)	0.0555 (17)	0.5214 (19)
C14	1.1077 (4)	0.1516 (9)	0.6101 (7)	0.068 (3)	0.5214 (19)
C15	1.1529 (4)	0.2292 (9)	0.5302 (7)	0.076 (3)	0.5214 (19)
H15	1.1171	0.2707	0.4733	0.092*	0.5214 (19)
C16	1.2513 (5)	0.2448 (9)	0.5352 (7)	0.073 (3)	0.5214 (19)
H16	1.2816	0.2968	0.4816	0.087*	0.5214 (19)
C17	1.3047 (5)	0.1829 (8)	0.6201 (7)	0.068 (3)	0.5214 (19)
H17	1.3707	0.1934	0.6234	0.081*	0.5214 (19)
C18	1.2595 (4)	0.1054 (9)	0.7000 (7)	0.070 (2)	0.5214 (19)
H18	1.2953	0.0638	0.7569	0.085*	0.5214 (19)
C19	1.1611 (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)
H9'1	0.8038	0.0595	0.5800	0.064*	0.4786 (19)
H9'2	0.8458	−0.0359	0.6748	0.064*	0.4786 (19)
C10'	1.0349 (5)	0.2273 (10)	0.4867 (7)	0.0667 (19)	0.4786 (19)
H10'	1.0368	0.2777	0.4209	0.080*	0.4786 (19)
C11'	0.9485 (6)	0.1796 (18)	0.5240 (12)	0.082 (4)	0.4786 (19)
H11'	0.8923	0.1996	0.4842	0.098*	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'	1.1986	0.0369	0.7658	0.092*	0.4786 (19)
C16'	1.2875 (6)	0.1393 (10)	0.6641 (9)	0.073 (3)	0.4786 (19)
H16'	1.3438	0.1188	0.7034	0.087*	0.4786 (19)
C17'	1.2901 (6)	0.2191 (10)	0.5678 (8)	0.068 (3)	0.4786 (19)
H17'	1.3482	0.2519	0.5428	0.081*	0.4786 (19)
C18'	1.2056 (5)	0.2498 (9)	0.5089 (7)	0.070 (2)	0.4786 (19)
H18'	1.2073	0.3031	0.4446	0.085*	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)
C1	0.7221 (3)	0.1315 (4)	0.7734 (3)	0.0451 (10)
C2	0.6685 (3)	0.0219 (5)	0.7571 (4)	0.0515 (11)
H2	0.6915	−0.0492	0.7149	0.062*
C3	0.5733 (3)	0.0146 (5)	0.8065 (4)	0.0525 (11)
C4	0.5388 (3)	0.1316 (5)	0.8710 (4)	0.0531 (11)
H4A	0.4962	0.1001	0.9288	0.064*
H4B	0.5020	0.1888	0.8204	0.064*
C5	0.6191 (3)	0.2159 (4)	0.9280 (3)	0.0471 (10)
C6	0.6897 (3)	0.2516 (4)	0.8369 (4)	0.0465 (10)
H6A	0.6598	0.3143	0.7846	0.056*
H6B	0.7448	0.2954	0.8714	0.056*
C7	0.6693 (4)	0.1348 (6)	1.0219 (4)	0.0652 (14)
H7A	0.7186	0.1882	1.0569	0.098*
H7B	0.6972	0.0558	0.9902	0.098*
H7C	0.6235	0.1095	1.0772	0.098*
C8	0.5763 (4)	0.3438 (6)	0.9770 (5)	0.0684 (14)
H8A	0.6263	0.3970	1.0107	0.103*
H8B	0.5307	0.3207	1.0332	0.103*
H8C	0.5450	0.3938	0.9178	0.103*
O1	0.8111 (2)	0.1500 (3)	0.7355 (3)	0.0642 (10)
O2	0.5246 (3)	−0.0871 (4)	0.7946 (3)	0.0814 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0660 (7)	0.0816 (11)	0.0705 (9)	0.0125 (6)	−0.0091 (5)	−0.0032 (7)
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)
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)
C1	0.043 (2)	0.050 (3)	0.042 (2)	0.0009 (19)	0.0091 (18)	0.0007 (19)
C2	0.051 (3)	0.054 (3)	0.050 (2)	−0.008 (2)	0.008 (2)	−0.009 (2)
C3	0.053 (3)	0.062 (3)	0.042 (2)	−0.017 (2)	−0.001 (2)	0.002 (2)
C4	0.042 (2)	0.064 (3)	0.053 (3)	−0.006 (2)	0.006 (2)	0.001 (2)
C5	0.041 (2)	0.057 (3)	0.043 (2)	−0.003 (2)	0.0087 (18)	−0.001 (2)
C6	0.045 (2)	0.051 (3)	0.044 (2)	−0.0027 (19)	0.0065 (18)	0.0026 (19)
C7	0.072 (3)	0.087 (4)	0.037 (2)	−0.014 (3)	0.001 (2)	0.010 (2)
C8	0.063 (3)	0.073 (3)	0.070 (3)	−0.004 (3)	0.015 (3)	−0.017 (3)
O1	0.0533 (19)	0.059 (2)	0.081 (2)	−0.0126 (15)	0.0272 (17)	−0.0207 (18)
O2	0.069 (2)	0.083 (3)	0.093 (3)	−0.035 (2)	0.018 (2)	−0.018 (2)

Geometric parameters (Å, º) top

Br1—C13	1.907 (6)	C13'—Br1'	1.897 (7)
C9—O1	1.461 (10)	C14'—C15'	1.395 (5)
C9—C12	1.515 (8)	C14'—C19'	1.395 (5)
C9—H9A	0.9700	C15'—C16'	1.395 (5)
C9—H9B	0.9700	C15'—H15'	0.9300
C10—C11	1.383 (6)	C16'—C17'	1.395 (5)
C10—C19	1.387 (6)	C16'—H16'	0.9300
C10—H10	0.9300	C17'—C18'	1.395 (5)
C11—C12	1.382 (6)	C17'—H17'	0.9300
C11—H11	0.9300	C18'—C19'	1.395 (5)
C12—C13	1.376 (6)	C18'—H18'	0.9300
C13—C14	1.390 (6)	C1—C2	1.339 (6)
C14—C19	1.386 (5)	C1—O1	1.345 (5)
C14—C15	1.386 (5)	C1—C6	1.493 (6)
C15—C16	1.386 (5)	C2—C3	1.467 (6)
C15—H15	0.9300	C2—H2	0.9300
C16—C17	1.386 (5)	C3—O2	1.231 (6)
C16—H16	0.9300	C3—C4	1.483 (7)
C17—C18	1.386 (5)	C4—C5	1.548 (6)
C17—H17	0.9300	C4—H4A	0.9700
C18—C19	1.386 (5)	C4—H4B	0.9700
C18—H18	0.9300	C5—C6	1.520 (6)
C9'—O1	1.499 (11)	C5—C8	1.531 (7)
C9'—C12'	1.519 (9)	C5—C7	1.536 (6)
C9'—H9'1	0.9700	C6—H6A	0.9700
C9'—H9'2	0.9700	C6—H6B	0.9700
C10'—C19'	1.379 (7)	C7—H7A	0.9600
C10'—C11'	1.380 (6)	C7—H7B	0.9600
C10'—H10'	0.9300	C7—H7C	0.9600
C11'—C12'	1.383 (6)	C8—H8A	0.9600
C11'—H11'	0.9300	C8—H8B	0.9600
C12'—C13'	1.377 (6)	C8—H8C	0.9600
C13'—C14'	1.389 (7)

O1—C9—C12	109.3 (7)	C14'—C15'—C16'	120.0
O1—C9—H9A	109.8	C14'—C15'—H15'	120.0
C12—C9—H9A	109.8	C16'—C15'—H15'	120.0
O1—C9—H9B	109.8	C15'—C16'—C17'	120.0
C12—C9—H9B	109.8	C15'—C16'—H16'	120.0
H9A—C9—H9B	108.3	C17'—C16'—H16'	120.0
C11—C10—C19	119.7 (4)	C18'—C17'—C16'	120.0
C11—C10—H10	120.2	C18'—C17'—H17'	120.0
C19—C10—H10	120.2	C16'—C17'—H17'	120.0
C12—C11—C10	120.1 (4)	C17'—C18'—C19'	120.0
C12—C11—H11	120.0	C17'—C18'—H18'	120.0
C10—C11—H11	120.0	C19'—C18'—H18'	120.0
C13—C12—C11	120.4 (4)	C10'—C19'—C18'	120.4 (4)
C13—C12—C9	125.5 (6)	C10'—C19'—C14'	119.6 (4)
C11—C12—C9	114.2 (6)	C18'—C19'—C14'	120.0
C12—C13—C14	120.0 (4)	C2—C1—O1	125.7 (4)
C12—C13—Br1	118.9 (4)	C2—C1—C6	123.7 (4)
C14—C13—Br1	121.1 (4)	O1—C1—C6	110.6 (4)
C19—C14—C15	120.0	C1—C2—C3	119.5 (4)
C19—C14—C13	119.6 (3)	C1—C2—H2	120.2
C15—C14—C13	120.4 (3)	C3—C2—H2	120.2
C16—C15—C14	120.0	O2—C3—C2	120.0 (4)
C16—C15—H15	120.0	O2—C3—C4	121.7 (4)
C14—C15—H15	120.0	C2—C3—C4	118.3 (4)
C17—C16—C15	120.0	C3—C4—C5	114.4 (4)
C17—C16—H16	120.0	C3—C4—H4A	108.7
C15—C16—H16	120.0	C5—C4—H4A	108.7
C16—C17—C18	120.0	C3—C4—H4B	108.7
C16—C17—H17	120.0	C5—C4—H4B	108.7
C18—C17—H17	120.0	H4A—C4—H4B	107.6
C17—C18—C19	120.0	C6—C5—C8	109.8 (4)
C17—C18—H18	120.0	C6—C5—C7	110.2 (4)
C19—C18—H18	120.0	C8—C5—C7	110.0 (4)
C14—C19—C18	120.0	C6—C5—C4	107.1 (3)
C14—C19—C10	120.2 (3)	C8—C5—C4	109.5 (4)
C18—C19—C10	119.8 (3)	C7—C5—C4	110.2 (4)
O1—C9'—C12'	104.8 (7)	C1—C6—C5	112.2 (3)
O1—C9'—H9'1	110.8	C1—C6—H6A	109.2
C12'—C9'—H9'1	110.8	C5—C6—H6A	109.2
O1—C9'—H9'2	110.8	C1—C6—H6B	109.2
C12'—C9'—H9'2	110.8	C5—C6—H6B	109.2
H9'1—C9'—H9'2	108.9	H6A—C6—H6B	107.9
C19'—C10'—C11'	120.5 (4)	C5—C7—H7A	109.5
C19'—C10'—H10'	119.8	C5—C7—H7B	109.5
C11'—C10'—H10'	119.8	H7A—C7—H7B	109.5
C10'—C11'—C12'	120.1 (4)	C5—C7—H7C	109.5
C10'—C11'—H11'	120.0	H7A—C7—H7C	109.5
C12'—C11'—H11'	120.0	H7B—C7—H7C	109.5
C13'—C12'—C11'	119.9 (4)	C5—C8—H8A	109.5
C13'—C12'—C9'	127.3 (7)	C5—C8—H8B	109.5
C11'—C12'—C9'	112.8 (7)	H8A—C8—H8B	109.5
C12'—C13'—C14'	120.4 (4)	C5—C8—H8C	109.5
C12'—C13'—Br1'	118.4 (4)	H8A—C8—H8C	109.5
C14'—C13'—Br1'	121.2 (4)	H8B—C8—H8C	109.5
C13'—C14'—C15'	120.5 (4)	C1—O1—C9	116.1 (4)
C13'—C14'—C19'	119.5 (4)	C1—O1—C9'	117.1 (4)
C15'—C14'—C19'	120.0	C9—O1—C9'	23.1 (5)

C19—C10—C11—C12	−1 (2)	C12'—C13'—C14'—C19'	−0.8 (14)
C10—C11—C12—C13	1 (2)	Br1'—C13'—C14'—C19'	179.6 (6)
C10—C11—C12—C9	−179.1 (13)	C13'—C14'—C15'—C16'	179.4 (11)
O1—C9—C12—C13	−75.3 (11)	C19'—C14'—C15'—C16'	0.0
O1—C9—C12—C11	104.4 (12)	C14'—C15'—C16'—C17'	0.0
C11—C12—C13—C14	0.6 (17)	C15'—C16'—C17'—C18'	0.0
C9—C12—C13—C14	−179.8 (9)	C16'—C17'—C18'—C19'	0.0
C11—C12—C13—Br1	178.9 (11)	C11'—C10'—C19'—C18'	−179.5 (12)
C9—C12—C13—Br1	−1.5 (13)	C11'—C10'—C19'—C14'	2.4 (17)
C12—C13—C14—C19	−1.6 (12)	C17'—C18'—C19'—C10'	−178.1 (10)
Br1—C13—C14—C19	−179.8 (5)	C17'—C18'—C19'—C14'	0.0
C12—C13—C14—C15	178.9 (7)	C13'—C14'—C19'—C10'	−1.3 (11)
Br1—C13—C14—C15	0.7 (11)	C15'—C14'—C19'—C10'	178.1 (10)
C19—C14—C15—C16	0.0	C13'—C14'—C19'—C18'	−179.4 (11)
C13—C14—C15—C16	179.5 (10)	C15'—C14'—C19'—C18'	0.0
C14—C15—C16—C17	0.0	O1—C1—C2—C3	178.3 (4)
C15—C16—C17—C18	0.0	C6—C1—C2—C3	−2.0 (7)
C16—C17—C18—C19	0.0	C1—C2—C3—O2	−178.0 (5)
C15—C14—C19—C18	0.0	C1—C2—C3—C4	1.4 (7)
C13—C14—C19—C18	−179.5 (10)	O2—C3—C4—C5	151.0 (4)
C15—C14—C19—C10	−179.0 (10)	C2—C3—C4—C5	−28.4 (6)
C13—C14—C19—C10	1.5 (10)	C3—C4—C5—C6	52.9 (5)
C17—C18—C19—C14	0.0	C3—C4—C5—C8	171.8 (4)
C17—C18—C19—C10	179.0 (9)	C3—C4—C5—C7	−67.0 (5)
C11—C10—C19—C14	−0.4 (15)	C2—C1—C6—C5	29.6 (6)
C11—C10—C19—C18	−179.4 (11)	O1—C1—C6—C5	−150.7 (4)
C19'—C10'—C11'—C12'	−1 (2)	C8—C5—C6—C1	−170.9 (4)
C10'—C11'—C12'—C13'	−1 (2)	C7—C5—C6—C1	67.8 (5)
C10'—C11'—C12'—C9'	−178.3 (14)	C4—C5—C6—C1	−52.1 (5)
O1—C9'—C12'—C13'	83.4 (12)	C2—C1—O1—C9	−11.2 (7)
O1—C9'—C12'—C11'	−99.3 (13)	C6—C1—O1—C9	169.1 (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—C1	−162.9 (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—C1	179.2 (6)
Br1'—C13'—C14'—C15'	0.2 (12)	C12'—C9'—O1—C9	−87.4 (13)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉BrO₂
M_r	359.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.986 (3), 9.9970 (18), 11.859 (2)
β (°)	91.169 (2)
V (Å³)	1657.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.48
Crystal size (mm)	0.32 × 0.29 × 0.27

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.504, 0.554
No. of measured, independent and observed [I > 2σ(I)] reflections	11934, 3075, 1931
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.199, 1.07
No. of reflections	3075
No. of parameters	222
No. of restraints	72
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.20

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

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

References

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