3,3′-Dibromo-5,5′-di-tert-butyl-2,2′-dimethoxy­biphen­yl

Polson, M.I.J.; Steel, P.J.

doi:10.1107/S1600536808002420

organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o532

doi:10.1107/S1600536808002420

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3,3′-Dibromo-5,5′-di-tert-butyl-2,2′-dimethoxybiphenyl

Matthew I. J. Polson ^a ^* and Peter J. Steel ^a

^aChemistry Department, University of Canterbury, PO Box 4800, Christchurch, New Zealand
^*Correspondence e-mail: matthew.polson@canterbury.ac.nz

(Received 9 November 2007; accepted 22 January 2008; online 30 January 2008)

The title compound, C₂₂H₂₈Br₂O₂, crystallizes in a staggered arrangement to minimize the interactions of its ortho substituents, with a dihedral angle of 84.2 (3)° between the two aromatic rings. Short C—H⋯O hydrogen-bonding interactions between methoxy groups result in a one-dimensional polymeric chain of molecules lying parallel to the b axis. One tert-butyl group is disordered equally over two positions.

Related literature

For a related structure, see: He & Ng (2006 ); Steiner (1996 ). For an alternative synthesis, see: Katagiri et al. (2006 ).

Experimental

Crystal data

C₂₂H₂₈Br₂O₂
M_r = 484.27
Monoclinic, C 2/c
a = 14.661 (2) Å
b = 13.408 (2) Å
c = 22.489 (3) Å
β = 96.104 (12)°
V = 4395.8 (11) Å³
Z = 8
Mo Kα radiation
μ = 3.70 mm⁻¹
T = 93 (2) K
0.40 × 0.12 × 0.10 mm

Data collection

Bruker APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.433, T_max = 0.691
14546 measured reflections
3918 independent reflections
2784 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.143
S = 1.10
3918 reflections
293 parameters
54 restraints
H-atom parameters constrained
Δρ_max = 1.10 e Å⁻³
Δρ_min = −0.93 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C31—H31C⋯O10ⁱ	0.98	2.61	2.842 (15)	94
C41—H41C⋯O21ⁱⁱ	0.98	2.57	2.866 (14)	98
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (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: ORTEP-3 for Windows (Version 1.08; Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002420/pv2045sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808002420/pv2045Isup2.hkl

checkCIF report

Comment top

During attempts to dilithiate 2,6-dibromo-4 - t-butylanisole, the title compound, (I), was serindipitously produced. Compared to the literature methods (Katagiri et al., 2006) this is a much simpler method, wherein the product was acheived in a single step rather than three and with a superior overall yield. The structure adopts a staggered arrangement with a dihedral angle of 84.2 (3)° between the two aromatic rings. A similar angle is found in the literature (80.1°, He & Ng, 2006). Two CH₃···O hydrogen bonds involving both methoxy groups (Table 1) connect the molecules to form a one dimensional polymeric chain parallel to the b axis (Figure 2); similar type of interactions have already been reported (Steiner, 1996).

Related literature top

For a related structures, see: He & Ng (2006); Steiner, (1996). For an alternative synthesis, see: Katagiri et al. (2006).

Experimental top

2,6-Dibromo-4 - t-butylanisole (1 g) in THF (40 ml) at 193 K was treated with n-butyl lithium (1.6 M, 2.5 ml). The solution was stirred and allowed to warm up to room temp over 2 hr. The resulting solution was evaporated to dryness, treated with water and extracted with dichloromethane. The organic layer was seperated and purified by column chromotography (SiO₂, dichloromethane). Yeild = 0.6 g (79%).

Computing details top

Data collection: APEX2 (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: ORTEP-3 for Windows (Version 1.08; Farrugia, 1997) and Mercury (Version 1.4; Bruno et al., 2002); software used to prepare material for publication: pubCIF (Westrip, 2008).

Figures top

	Fig. 1. A view of the asymmetric unit of (I), showing displacement ellipsoids at the 50% probability level. All hydrogen atoms have been omited for clarity. The bonds for one of the disordered parts are displayed as hollow bonds.
	Fig. 2. A diagram showing the hydrogen bonding which extends the structure into a 1-D polymer. The closest C—H···O bonds are shown as dashed lines.

3,3'-Dibromo-5,5'-di-tert-butyl-2,2'-dimethoxybiphenyl top

Crystal data top

C₂₂H₂₈Br₂O₂	F(000) = 1968
M_r = 484.27	D_x = 1.463 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4881 reflections
a = 14.661 (2) Å	θ = 2.8–26.5°
b = 13.408 (2) Å	µ = 3.70 mm⁻¹
c = 22.489 (3) Å	T = 93 K
β = 96.104 (12)°	Shard, colourless
V = 4395.8 (11) Å³	0.40 × 0.12 × 0.10 mm
Z = 8

Data collection top

Bruker APEX2 CCD area-detector diffractometer	3918 independent reflections
Radiation source: sealed tube	2784 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −17→17
T_min = 0.433, T_max = 0.691	k = −14→16
14546 measured reflections	l = −18→26

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0562P)² + 0.5007P] where P = (F_o² + 2F_c²)/3
3918 reflections	(Δ/σ)_max < 0.001
293 parameters	Δρ_max = 1.11 e Å⁻³
54 restraints	Δρ_min = −0.93 e Å⁻³

Crystal data top

C₂₂H₂₈Br₂O₂	V = 4395.8 (11) Å³
M_r = 484.27	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 14.661 (2) Å	µ = 3.70 mm⁻¹
b = 13.408 (2) Å	T = 93 K
c = 22.489 (3) Å	0.40 × 0.12 × 0.10 mm
β = 96.104 (12)°

Data collection top

Bruker APEX2 CCD area-detector diffractometer	3918 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2784 reflections with I > 2σ(I)
T_min = 0.433, T_max = 0.691	R_int = 0.077
14546 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	54 restraints
wR(F²) = 0.143	H-atom parameters constrained
S = 1.10	Δρ_max = 1.11 e Å⁻³
3918 reflections	Δρ_min = −0.93 e Å⁻³
293 parameters

Special details top

Experimental. Spectroscopic data: ¹H NMR (CDCl₃): δ 1.33 (18H, s, (CH₃)₃), 3.53 (6H, s, OCH₃), 7.36 (2H, d, ArH), 7.57 (2H, d, ArH). Mass Spec: (ESI-TOF) 485.3 {M+} calc 485.05.

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)
Br10	0.15107 (7)	0.73599 (8)	0.05847 (4)	0.0641 (3)
C10	0.2414 (5)	0.7782 (5)	0.1739 (3)	0.0318 (16)
C11	0.2365 (5)	0.8029 (6)	0.1143 (3)	0.0384 (18)
C12	0.2911 (5)	0.8769 (6)	0.0943 (3)	0.0395 (18)
H12	0.2846	0.8937	0.0531	0.047*
C13	0.3553 (5)	0.9273 (5)	0.1330 (3)	0.0319 (16)
C14	0.3623 (5)	0.8991 (5)	0.1932 (3)	0.0305 (16)
H14	0.4073	0.9302	0.2206	0.037*
C15	0.3053 (4)	0.8267 (5)	0.2143 (3)	0.0278 (15)
C16	0.4181 (6)	1.0090 (5)	0.1119 (3)	0.0404 (18)
Br21	0.18307 (6)	0.87188 (6)	0.42817 (3)	0.0464 (2)
C20	0.3129 (4)	0.7995 (5)	0.2790 (3)	0.0264 (15)
C21	0.2538 (4)	0.8409 (5)	0.3166 (3)	0.0264 (15)
C22	0.2626 (4)	0.8137 (5)	0.3765 (3)	0.0268 (15)
C23	0.3269 (4)	0.7445 (5)	0.3990 (3)	0.0285 (15)
H23	0.3308	0.7263	0.4400	0.034*
C24	0.3863 (4)	0.7008 (5)	0.3618 (3)	0.0247 (14)
C25	0.3790 (4)	0.7306 (5)	0.3025 (3)	0.0265 (14)
H25	0.4202	0.7035	0.2769	0.032*
C26	0.4557 (5)	0.6205 (5)	0.3860 (3)	0.0317 (16)
O21	0.1887 (3)	0.9095 (3)	0.2945 (2)	0.0332 (11)
C30	0.0955 (9)	0.8615 (11)	0.2798 (7)	0.042 (4)	0.50
H30A	0.1009	0.8049	0.2528	0.062*	0.50
H30B	0.0526	0.9105	0.2603	0.062*	0.50
H30C	0.0726	0.8379	0.3167	0.062*	0.50
C31	0.2269 (10)	1.0158 (10)	0.2987 (6)	0.037 (3)	0.50
H31A	0.2469	1.0319	0.3405	0.055*	0.50
H31B	0.1790	1.0628	0.2830	0.055*	0.50
H31C	0.2792	1.0208	0.2751	0.055*	0.50
O10	0.1857 (3)	0.7052 (3)	0.1937 (2)	0.0349 (11)
C40	0.0985 (9)	0.7443 (12)	0.2011 (7)	0.043 (4)	0.50
H40A	0.1045	0.7958	0.2322	0.064*	0.50
H40B	0.0587	0.6908	0.2130	0.064*	0.50
H40C	0.0716	0.7736	0.1634	0.064*	0.50
C41	0.2209 (10)	0.5993 (9)	0.1949 (6)	0.036 (3)	0.50
H41A	0.2306	0.5786	0.1542	0.054*	0.50
H41B	0.1760	0.5550	0.2105	0.054*	0.50
H41C	0.2791	0.5955	0.2206	0.054*	0.50
C50	0.4475 (12)	0.5886 (13)	0.4517 (7)	0.050 (4)	0.50
H50A	0.4877	0.5314	0.4619	0.075*	0.50
H50B	0.3838	0.5699	0.4559	0.075*	0.50
H50C	0.4657	0.6442	0.4786	0.075*	0.50
C51	0.4383 (12)	0.5241 (12)	0.3484 (7)	0.052 (4)	0.50
H51A	0.4576	0.5346	0.3085	0.078*	0.50
H51B	0.3728	0.5078	0.3449	0.078*	0.50
H51C	0.4735	0.4690	0.3682	0.078*	0.50
C52	0.5535 (11)	0.6565 (13)	0.3834 (8)	0.053 (4)	0.50
H52A	0.5635	0.7177	0.4070	0.080*	0.50
H52B	0.5636	0.6699	0.3418	0.080*	0.50
H52C	0.5965	0.6050	0.3999	0.080*	0.50
C60	0.4038 (11)	0.5287 (11)	0.3985 (7)	0.043 (4)	0.50
H60A	0.3881	0.4918	0.3612	0.065*	0.50
H60B	0.3474	0.5473	0.4155	0.065*	0.50
H60C	0.4416	0.4866	0.4269	0.065*	0.50
C61	0.5257 (11)	0.6015 (12)	0.3413 (7)	0.045 (4)	0.50
H61A	0.5465	0.6654	0.3264	0.067*	0.50
H61B	0.4971	0.5619	0.3077	0.067*	0.50
H61C	0.5784	0.5651	0.3612	0.067*	0.50
C62	0.5094 (10)	0.6633 (11)	0.4442 (6)	0.038 (3)	0.50
H62A	0.5527	0.6131	0.4618	0.057*	0.50
H62B	0.4661	0.6806	0.4728	0.057*	0.50
H62C	0.5431	0.7232	0.4343	0.057*	0.50
C70	0.4117 (9)	1.0992 (9)	0.1512 (5)	0.103 (4)
H70A	0.4498	1.0889	0.1892	0.155*
H70B	0.3477	1.1092	0.1588	0.155*
H70C	0.4333	1.1582	0.1311	0.155*
C71	0.3892 (7)	1.0442 (8)	0.0495 (4)	0.079 (3)
H71A	0.4268	1.1015	0.0404	0.119*
H71B	0.3245	1.0640	0.0461	0.119*
H71C	0.3973	0.9902	0.0212	0.119*
C72	0.5157 (6)	0.9717 (7)	0.1155 (4)	0.065 (3)
H72A	0.5559	1.0256	0.1047	0.098*
H72B	0.5193	0.9157	0.0879	0.098*
H72C	0.5353	0.9495	0.1564	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br10	0.0766 (7)	0.0720 (7)	0.0396 (5)	−0.0096 (5)	−0.0125 (4)	−0.0105 (5)
C10	0.030 (4)	0.038 (4)	0.027 (4)	0.015 (3)	0.003 (3)	0.001 (3)
C11	0.040 (4)	0.046 (5)	0.029 (4)	0.013 (4)	−0.002 (3)	−0.007 (3)
C12	0.051 (5)	0.049 (5)	0.019 (3)	0.008 (4)	0.006 (3)	0.004 (3)
C13	0.035 (4)	0.034 (4)	0.027 (4)	0.008 (3)	0.005 (3)	0.003 (3)
C14	0.033 (4)	0.028 (4)	0.032 (4)	0.002 (3)	0.009 (3)	0.001 (3)
C15	0.028 (4)	0.026 (4)	0.030 (4)	0.010 (3)	0.007 (3)	0.000 (3)
C16	0.065 (5)	0.029 (4)	0.029 (4)	0.004 (4)	0.012 (4)	0.004 (3)
Br21	0.0562 (5)	0.0481 (5)	0.0387 (4)	0.0201 (4)	0.0232 (3)	0.0043 (4)
C20	0.026 (4)	0.028 (4)	0.025 (3)	−0.003 (3)	0.002 (3)	0.000 (3)
C21	0.020 (3)	0.021 (3)	0.039 (4)	0.001 (3)	0.007 (3)	0.003 (3)
C22	0.026 (4)	0.026 (4)	0.029 (4)	0.002 (3)	0.004 (3)	−0.001 (3)
C23	0.035 (4)	0.028 (4)	0.023 (3)	−0.005 (3)	0.007 (3)	−0.003 (3)
C24	0.028 (4)	0.022 (3)	0.024 (3)	−0.002 (3)	0.005 (3)	0.001 (3)
C25	0.028 (4)	0.028 (4)	0.023 (3)	−0.001 (3)	0.001 (3)	0.000 (3)
C26	0.035 (4)	0.033 (4)	0.028 (4)	0.008 (3)	0.006 (3)	0.008 (3)
O21	0.032 (3)	0.027 (3)	0.041 (3)	0.004 (2)	0.008 (2)	0.007 (2)
C30	0.035 (8)	0.034 (9)	0.054 (9)	0.008 (7)	−0.009 (7)	0.008 (7)
C31	0.057 (10)	0.033 (8)	0.022 (7)	0.006 (7)	0.009 (7)	−0.003 (6)
O10	0.033 (3)	0.034 (3)	0.038 (3)	0.002 (2)	0.006 (2)	0.000 (2)
C40	0.027 (8)	0.053 (10)	0.046 (9)	−0.008 (7)	−0.004 (6)	0.000 (8)
C41	0.039 (8)	0.022 (8)	0.047 (9)	−0.013 (6)	0.004 (7)	0.005 (6)
C50	0.059 (8)	0.052 (8)	0.039 (7)	0.015 (7)	0.008 (6)	0.018 (6)
C51	0.062 (8)	0.040 (7)	0.050 (7)	0.015 (7)	−0.006 (7)	−0.001 (6)
C52	0.045 (7)	0.056 (8)	0.059 (8)	0.007 (7)	0.008 (6)	0.015 (7)
C60	0.047 (7)	0.031 (7)	0.052 (7)	−0.004 (6)	0.004 (6)	0.008 (6)
C61	0.042 (7)	0.053 (8)	0.039 (7)	0.015 (6)	0.007 (6)	0.000 (6)
C62	0.046 (7)	0.038 (7)	0.029 (6)	0.006 (6)	0.001 (6)	0.014 (6)
C70	0.126 (6)	0.085 (5)	0.104 (5)	−0.007 (4)	0.035 (4)	0.003 (4)
C71	0.075 (5)	0.090 (5)	0.072 (5)	−0.009 (4)	0.010 (4)	0.027 (4)
C72	0.059 (4)	0.058 (4)	0.078 (4)	−0.011 (4)	0.005 (4)	0.019 (4)

Geometric parameters (Å, º) top

Br10—C11	1.902 (7)	C31—H31B	0.9800
C10—C11	1.375 (9)	C31—H31C	0.9800
C10—O10	1.379 (8)	O10—C40	1.408 (15)
C10—C15	1.394 (9)	O10—C41	1.511 (14)
C11—C12	1.379 (10)	C40—H40A	0.9800
C12—C13	1.388 (10)	C40—H40B	0.9800
C12—H12	0.9500	C40—H40C	0.9800
C13—C14	1.398 (9)	C41—H41A	0.9800
C13—C16	1.539 (10)	C41—H41B	0.9800
C14—C15	1.397 (9)	C41—H41C	0.9800
C14—H14	0.9500	C50—H50A	0.9800
C15—C20	1.493 (9)	C50—H50B	0.9800
C16—C71	1.499 (11)	C50—H50C	0.9800
C16—C70	1.507 (13)	C51—H51A	0.9800
C16—C72	1.510 (11)	C51—H51B	0.9800
Br21—C22	1.899 (6)	C51—H51C	0.9800
C20—C21	1.390 (9)	C52—H52A	0.9800
C20—C25	1.401 (9)	C52—H52B	0.9800
C21—O21	1.380 (7)	C52—H52C	0.9800
C21—C22	1.388 (9)	C60—H60A	0.9800
C22—C23	1.380 (9)	C60—H60B	0.9800
C23—C24	1.398 (9)	C60—H60C	0.9800
C23—H23	0.9500	C61—H61A	0.9800
C24—C25	1.385 (8)	C61—H61B	0.9800
C24—C26	1.541 (9)	C61—H61C	0.9800
C25—H25	0.9500	C62—H62A	0.9800
C26—C60	1.489 (15)	C62—H62B	0.9800
C26—C52	1.519 (17)	C62—H62C	0.9800
C26—C61	1.533 (15)	C70—H70A	0.9800
C26—C51	1.550 (17)	C70—H70B	0.9800
C26—C50	1.555 (15)	C70—H70C	0.9800
C26—C62	1.563 (15)	C71—H71A	0.9800
O21—C30	1.516 (14)	C71—H71B	0.9800
O21—C31	1.530 (15)	C71—H71C	0.9800
C30—H30A	0.9800	C72—H72A	0.9800
C30—H30B	0.9800	C72—H72B	0.9800
C30—H30C	0.9800	C72—H72C	0.9800
C31—H31A	0.9800

C11—C10—O10	121.0 (6)	O21—C30—H30A	109.5
C11—C10—C15	119.0 (7)	O21—C30—H30B	109.5
O10—C10—C15	120.0 (6)	O21—C30—H30C	109.5
C10—C11—C12	121.3 (7)	O21—C31—H31A	109.5
C10—C11—Br10	119.5 (6)	O21—C31—H31B	109.5
C12—C11—Br10	119.2 (5)	H31A—C31—H31B	109.5
C11—C12—C13	121.6 (6)	O21—C31—H31C	109.5
C11—C12—H12	119.2	H31A—C31—H31C	109.5
C13—C12—H12	119.2	H31B—C31—H31C	109.5
C12—C13—C14	116.8 (6)	C10—O10—C40	110.5 (8)
C12—C13—C16	122.8 (6)	C10—O10—C41	117.3 (7)
C14—C13—C16	120.5 (6)	C40—O10—C41	131.4 (9)
C15—C14—C13	122.1 (6)	O10—C40—H40A	109.5
C15—C14—H14	118.9	O10—C40—H40B	109.5
C13—C14—H14	118.9	H40A—C40—H40B	109.5
C10—C15—C14	119.2 (6)	O10—C40—H40C	109.5
C10—C15—C20	119.8 (6)	H40A—C40—H40C	109.5
C14—C15—C20	121.1 (6)	H40B—C40—H40C	109.5
C71—C16—C70	105.5 (8)	O10—C41—H41A	109.5
C71—C16—C72	109.2 (7)	O10—C41—H41B	109.5
C70—C16—C72	110.6 (8)	O10—C41—H41C	109.5
C71—C16—C13	113.3 (7)	C26—C50—H50A	109.5
C70—C16—C13	108.3 (7)	C26—C50—H50B	109.5
C72—C16—C13	110.0 (6)	C26—C50—H50C	109.5
C21—C20—C25	119.0 (6)	C26—C51—H51A	109.5
C21—C20—C15	120.6 (6)	C26—C51—H51B	109.5
C25—C20—C15	120.4 (6)	C26—C51—H51C	109.5
O21—C21—C22	121.0 (5)	C26—C52—H52A	109.5
O21—C21—C20	120.0 (6)	C26—C52—H52B	109.5
C22—C21—C20	119.0 (6)	C26—C52—H52C	109.5
C23—C22—C21	121.5 (6)	C26—C60—H60A	109.5
C23—C22—Br21	119.5 (5)	C26—C60—H60B	109.5
C21—C22—Br21	119.0 (5)	H60A—C60—H60B	109.5
C22—C23—C24	120.4 (6)	C26—C60—H60C	109.5
C22—C23—H23	119.8	H60A—C60—H60C	109.5
C24—C23—H23	119.8	H60B—C60—H60C	109.5
C25—C24—C23	117.8 (6)	C26—C61—H61A	109.5
C25—C24—C26	121.5 (5)	C26—C61—H61B	109.5
C23—C24—C26	120.7 (5)	H61A—C61—H61B	109.5
C24—C25—C20	122.2 (6)	C26—C61—H61C	109.5
C24—C25—H25	118.9	H61A—C61—H61C	109.5
C20—C25—H25	118.9	H61B—C61—H61C	109.5
C60—C26—C52	140.6 (10)	C26—C62—H62A	109.5
C60—C26—C61	112.2 (10)	C26—C62—H62B	109.5
C52—C26—C61	47.7 (9)	H62A—C62—H62B	109.5
C60—C26—C24	108.2 (8)	C26—C62—H62C	109.5
C52—C26—C24	110.8 (8)	H62A—C62—H62C	109.5
C61—C26—C24	110.4 (7)	H62B—C62—H62C	109.5
C60—C26—C51	49.9 (9)	C16—C70—H70A	109.5
C52—C26—C51	110.2 (11)	C16—C70—H70B	109.5
C61—C26—C51	65.6 (10)	H70A—C70—H70B	109.5
C24—C26—C51	109.0 (8)	C16—C70—H70C	109.5
C60—C26—C50	60.0 (9)	H70A—C70—H70C	109.5
C52—C26—C50	107.0 (10)	H70B—C70—H70C	109.5
C61—C26—C50	134.6 (9)	C16—C71—H71A	109.5
C24—C26—C50	114.4 (7)	C16—C71—H71B	109.5
C51—C26—C50	105.3 (10)	H71A—C71—H71B	109.5
C60—C26—C62	111.6 (9)	C16—C71—H71C	109.5
C52—C26—C62	61.4 (9)	H71A—C71—H71C	109.5
C61—C26—C62	107.3 (9)	H71B—C71—H71C	109.5
C24—C26—C62	107.1 (7)	C16—C72—H72A	109.5
C51—C26—C62	143.3 (9)	C16—C72—H72B	109.5
C50—C26—C62	52.4 (8)	H72A—C72—H72B	109.5
C21—O21—C30	111.6 (7)	C16—C72—H72C	109.5
C21—O21—C31	111.4 (7)	H72A—C72—H72C	109.5
C30—O21—C31	136.5 (8)	H72B—C72—H72C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C31—H31C···O10ⁱ	0.98	2.61	2.842 (15)	94
C41—H41C···O21ⁱⁱ	0.98	2.57	2.866 (14)	98

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₈Br₂O₂
M_r	484.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	93
a, b, c (Å)	14.661 (2), 13.408 (2), 22.489 (3)
β (°)	96.104 (12)
V (Å³)	4395.8 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.70
Crystal size (mm)	0.40 × 0.12 × 0.10

Data collection
Diffractometer	Bruker APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.433, 0.691
No. of measured, independent and observed [I > 2σ(I)] reflections	14546, 3918, 2784
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.143, 1.10
No. of reflections	3918
No. of parameters	293
No. of restraints	54
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.11, −0.93

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Version 1.08; Farrugia, 1997) and Mercury (Version 1.4; Bruno et al., 2002), pubCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C31—H31C···O10ⁱ	0.98	2.61	2.842 (15)	94
C41—H41C···O21ⁱⁱ	0.98	2.57	2.866 (14)	98

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

We thank the Foundation of Research Science and Technology for funding. PJS also thanks the Royal Society of New Zealand for the award of a James Cook Research Fellowship.

References

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