3,3'-Dibromo-5,5'-di-tert-butyl-2,2'-dimethoxy-biphen-yl.

The title compound, C(22)H(28)Br(2)O(2), crystallizes in a staggered arrangement to minimize the inter-actions of its ortho substituents, with a dihedral angle of 84.2 (3)° between the two aromatic rings. Short C-H⋯O hydrogen-bonding inter-actions between meth-oxy groups result in a one-dimensional polymeric chain of mol-ecules 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 = 484.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.143

S = 1.10

3918 reflections

293 parameters

54 restraints

H-atom parameters constrained

Δρmax = 1.10 e Å−3

Δρmin = −0.93 e Å−3

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 ▶).

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

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

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

C22H28Br2O2	F000 = 1968
Mr = 484.27	Dx = 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 = 2.8–26.5º
b = 13.408 (2) Å	µ = 3.70 mm−1
c = 22.489 (3) Å	T = 93 (2) K
β = 96.104 (12)º	Shard, colourless
V = 4395.8 (11) Å3	0.40 × 0.12 × 0.10 mm
Z = 8

Bruker APEX2 CCD area-detector diffractometer	3918 independent reflections
Radiation source: sealed tube	2784 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.077
T = 93(2) K	θmax = 25.1º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2007)	h = −17→17
Tmin = 0.433, Tmax = 0.691	k = −14→16
14546 measured reflections	l = −18→26

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067	H-atom parameters constrained
wR(F2) = 0.143	w = 1/[σ2(Fo2) + (0.0562P)2 + 0.5007P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
3918 reflections	Δρmax = 1.11 e Å−3
293 parameters	Δρmin = −0.93 e Å−3
54 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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

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

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) ; (ii) .