Crystal structure of 5,5'-di-bromo-3,3'-di-tert-butyl-6,6'-di-methyl-biphenyl-2,2'-diol.

The whole mol-ecule of the title compound, C22H28Br2O2, is generated by twofold rotation symmetry. The dihedral angle of the biphenyl moiety is 85.05 (11)°. The hy-droxy groups show intra-molecular O-H⋯π inter-actions without any other hydrogen-bond acceptors. In the crystal, there are no other significant inter-molecular inter-actions present.

Related literature

For the synthesis of the title compound using a transition-metal catalyst, see: Kubota et al. (2012 ▸). For the determination of the absolute configuration of the corresponding (+)-chloro derivative, viz. S, see: Gutierrez et al. (2010 ▸). For the crystal structure of a similar compound, i.e. 5,5′-dimeth­oxy-6,6′-di­methyl­biphenyl-2,2′-diol di­chloro­methane solvate, see: Guo et al. (2011 ▸).

Experimental

Crystal data

C22H28Br2O2

M = 484.24

Orthorhombic,

a = 7.3680 (5) Å

b = 22.4243 (14) Å

c = 6.6148 (4) Å

V = 1092.91 (12) Å3

Z = 2

Mo Kα radiation

μ = 3.72 mm−1

T = 299 K

0.16 × 0.15 × 0.10 mm

Data collection

Bruker D8 VENTURE diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.630, T max = 0.773

9406 measured reflections

1966 independent reflections

1615 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.065

S = 1.06

1966 reflections

123 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack x determined using 621 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: 0.034 (9)

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXL2014 and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015006313/su5104sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006313/su5104Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006313/su5104Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015006313/su5104fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015006313/su5104fig2.tif

The synthesis of the title compound, (I).

CCDC reference: 1056738

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H28Br2O2	Dx = 1.472 Mg m−3
Mr = 484.24	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pba2	Cell parameters from 4121 reflections
a = 7.3680 (5) Å	θ = 2.9–23.6°
b = 22.4243 (14) Å	µ = 3.72 mm−1
c = 6.6148 (4) Å	T = 299 K
V = 1092.91 (12) Å3	Prism, colourless
Z = 2	0.16 × 0.15 × 0.10 mm
F(000) = 492

Bruker D8 VENTURE diffractometer	1615 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
ω scans	θmax = 25.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −8→8
Tmin = 0.630, Tmax = 0.773	k = −26→26
9406 measured reflections	l = −7→7
1966 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0176P)2 + 0.3778P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.065	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.48 e Å−3
1966 reflections	Δρmin = −0.21 e Å−3
123 parameters	Absolute structure: Flack x determined using 621 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.034 (9)
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
Br1	1.18668 (8)	0.81211 (2)	0.48288 (15)	0.0681 (2)
O2	0.7528 (4)	0.98204 (13)	0.9897 (9)	0.0576 (8)
H2	0.7777	1.0166	0.9607	0.086*
C3	0.9856 (6)	0.96676 (17)	0.7429 (7)	0.0352 (10)
C4	1.0903 (6)	0.9290 (2)	0.6223 (7)	0.0388 (11)
C5	1.0536 (6)	0.8689 (2)	0.6397 (7)	0.0399 (11)
C6	0.9212 (6)	0.84644 (19)	0.7649 (7)	0.0394 (11)
H6	0.9023	0.8054	0.7685	0.047*
C7	0.8150 (6)	0.88292 (19)	0.8859 (7)	0.0360 (10)
C8	0.8518 (6)	0.94415 (19)	0.8707 (7)	0.0370 (11)
C9	1.2322 (7)	0.9538 (2)	0.4852 (15)	0.0650 (14)
H9A	1.1993	0.9460	0.3473	0.098*
H9B	1.3467	0.9353	0.5143	0.098*
H9C	1.2417	0.9960	0.5058	0.098*
C10	0.6668 (5)	0.8582 (2)	1.0234 (8)	0.0428 (15)
C11	0.6564 (7)	0.7905 (2)	1.0111 (14)	0.074 (2)
H11A	0.6243	0.7789	0.8761	0.111*
H11B	0.5661	0.7762	1.1039	0.111*
H11C	0.7722	0.7737	1.0456	0.111*
C12	0.7053 (8)	0.8746 (3)	1.2449 (9)	0.0756 (18)
H12A	0.8260	0.8623	1.2802	0.113*
H12B	0.6195	0.8548	1.3311	0.113*
H12C	0.6944	0.9170	1.2619	0.113*
C13	0.4827 (6)	0.8829 (2)	0.9625 (15)	0.0760 (17)
H13A	0.4791	0.9249	0.9894	0.114*
H13B	0.3893	0.8632	1.0387	0.114*
H13C	0.4634	0.8760	0.8208	0.114*

	U11	U22	U33	U12	U13	U23
Br1	0.0866 (4)	0.0458 (3)	0.0718 (4)	0.0118 (2)	0.0311 (4)	−0.0118 (4)
O2	0.0646 (19)	0.0366 (16)	0.072 (2)	0.0049 (14)	0.018 (3)	−0.009 (3)
C3	0.040 (3)	0.030 (2)	0.036 (3)	0.0016 (19)	−0.004 (2)	0.001 (2)
C4	0.048 (3)	0.033 (3)	0.035 (3)	0.003 (2)	0.002 (2)	0.000 (2)
C5	0.048 (3)	0.035 (3)	0.037 (3)	0.009 (2)	0.003 (2)	−0.003 (2)
C6	0.046 (3)	0.028 (2)	0.045 (3)	0.002 (2)	−0.002 (2)	−0.002 (2)
C7	0.036 (3)	0.034 (2)	0.038 (2)	0.008 (2)	−0.005 (2)	−0.002 (2)
C8	0.042 (3)	0.031 (3)	0.038 (2)	0.006 (2)	0.000 (2)	−0.005 (2)
C9	0.084 (3)	0.048 (3)	0.063 (3)	0.003 (2)	0.033 (5)	−0.003 (5)
C10	0.035 (3)	0.045 (3)	0.048 (4)	−0.0010 (19)	0.008 (3)	0.003 (2)
C11	0.070 (3)	0.048 (3)	0.104 (6)	−0.013 (2)	0.036 (5)	0.008 (4)
C12	0.078 (4)	0.099 (5)	0.049 (4)	−0.021 (4)	0.010 (3)	0.002 (3)
C13	0.039 (3)	0.086 (4)	0.103 (5)	0.005 (2)	0.012 (4)	0.020 (5)

Br1—C5	1.913 (4)	C9—H9B	0.9600
O2—C8	1.369 (6)	C9—H9C	0.9600
O2—H2	0.8200	C10—C13	1.520 (7)
C3—C8	1.394 (6)	C10—C11	1.521 (7)
C3—C4	1.396 (6)	C10—C12	1.537 (8)
C3—C3i	1.506 (8)	C11—H11A	0.9600
C4—C5	1.379 (6)	C11—H11B	0.9600
C4—C9	1.491 (8)	C11—H11C	0.9600
C5—C6	1.375 (6)	C12—H12A	0.9600
C6—C7	1.386 (6)	C12—H12B	0.9600
C6—H6	0.9300	C12—H12C	0.9600
C7—C8	1.403 (6)	C13—H13A	0.9600
C7—C10	1.526 (6)	C13—H13B	0.9600
C9—H9A	0.9600	C13—H13C	0.9600
C8—O2—H2	109.5	C13—C10—C11	107.7 (4)
C8—C3—C4	121.1 (4)	C13—C10—C7	110.4 (5)
C8—C3—C3i	117.3 (4)	C11—C10—C7	111.5 (4)
C4—C3—C3i	121.6 (4)	C13—C10—C12	109.3 (5)
C5—C4—C3	115.9 (4)	C11—C10—C12	107.4 (5)
C5—C4—C9	123.5 (4)	C7—C10—C12	110.5 (4)
C3—C4—C9	120.5 (4)	C10—C11—H11A	109.5
C6—C5—C4	123.2 (4)	C10—C11—H11B	109.5
C6—C5—Br1	116.5 (3)	H11A—C11—H11B	109.5
C4—C5—Br1	120.3 (3)	C10—C11—H11C	109.5
C5—C6—C7	122.2 (4)	H11A—C11—H11C	109.5
C5—C6—H6	118.9	H11B—C11—H11C	109.5
C7—C6—H6	118.9	C10—C12—H12A	109.5
C6—C7—C8	115.3 (4)	C10—C12—H12B	109.5
C6—C7—C10	122.2 (4)	H12A—C12—H12B	109.5
C8—C7—C10	122.5 (4)	C10—C12—H12C	109.5
O2—C8—C3	120.0 (4)	H12A—C12—H12C	109.5
O2—C8—C7	117.6 (4)	H12B—C12—H12C	109.5
C3—C8—C7	122.4 (4)	C10—C13—H13A	109.5
C4—C9—H9A	109.5	C10—C13—H13B	109.5
C4—C9—H9B	109.5	H13A—C13—H13B	109.5
H9A—C9—H9B	109.5	C10—C13—H13C	109.5
C4—C9—H9C	109.5	H13A—C13—H13C	109.5
H9A—C9—H9C	109.5	H13B—C13—H13C	109.5
H9B—C9—H9C	109.5
C8—C3—C4—C5	−0.5 (6)	C3i—C3—C8—O2	0.0 (6)
C3i—C3—C4—C5	178.5 (4)	C4—C3—C8—C7	0.1 (7)
C8—C3—C4—C9	179.6 (5)	C3i—C3—C8—C7	−179.0 (4)
C3i—C3—C4—C9	−1.4 (7)	C6—C7—C8—O2	−178.9 (4)
C3—C4—C5—C6	0.9 (7)	C10—C7—C8—O2	1.9 (6)
C9—C4—C5—C6	−179.3 (6)	C6—C7—C8—C3	0.1 (6)
C3—C4—C5—Br1	179.9 (3)	C10—C7—C8—C3	−179.1 (4)
C9—C4—C5—Br1	−0.2 (7)	C6—C7—C10—C13	−118.6 (5)
C4—C5—C6—C7	−0.8 (7)	C8—C7—C10—C13	60.5 (6)
Br1—C5—C6—C7	−179.8 (3)	C6—C7—C10—C11	1.0 (6)
C5—C6—C7—C8	0.3 (7)	C8—C7—C10—C11	−179.8 (5)
C5—C6—C7—C10	179.4 (4)	C6—C7—C10—C12	120.4 (5)
C4—C3—C8—O2	179.0 (4)	C8—C7—C10—C12	−60.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cgi	0.82	2.54	3.047 (5)	122

Table 1

Hydrogen-bond geometry (, )

Cg is the centroid of benzene ring C3C8.

DHA	DH	HA	D A	DHA
O2H2Cg i	0.82	2.54	3.047(5)	122

Symmetry code: (i) .