3-[(1-Bromo-naphthalen-2-yl)meth-oxy]-5,5-di-methyl-cyclo-hex-2-enone.

In the title compound, C19H19BrO2, the cyclo-hexenone 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 mol-ecules, 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 = 359.25

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.199

S = 1.07

3075 reflections

222 parameters

72 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301026X/xu5694sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301026X/xu5694Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301026X/xu5694Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301026X/xu5694Isup4.cml

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

C19H19BrO2	F(000) = 736
Mr = 359.25	Dx = 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

Bruker SMART 1000 CCD area-detector diffractometer	3075 independent reflections
Radiation source: fine-focus sealed tube	1931 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
phi and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −16→16
Tmin = 0.504, Tmax = 0.554	k = −12→12
11934 measured reflections	l = −14→14

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(Fo2) + (0.0635P)2 + 1.8223P] where P = (Fo2 + 2Fc2)/3
3075 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.26 e Å−3
72 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)