3,3'-Di-tert-butyl-5,5'-dimethoxy-biphenyl-2,2'-diol.

The title compound, C(22)H(30)O(4), displays twofold rotational symmetry. The two benzene rings are almost perpendicular to each other, forming a dihedral angle of 89.8 (6)°. In the crystal, mol-ecules are linked into an extended one-dimensional chain structure via inter-molecular O-H⋯O hydrogen bonds.

Related literature

For the various methods of preparing di-BHA [a dimer of 3-tert-butyl-4-hydroxy­anisole], see: Hewgill & Hewitt (1967 ▶); Jarl et al. (2004 ▶); Masahiro et al. (2005 ▶); Seiichiro et al. (2004 ▶).

Experimental

Crystal data

C22H30O4

M = 358.46

Tetragonal,

a = 13.4289 (8) Å

c = 23.127 (3) Å

V = 4170.5 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 291 K

0.49 × 0.49 × 0.38 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.963, T max = 0.972

13638 measured reflections

1938 independent reflections

1542 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.112

S = 1.04

1938 reflections

123 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023071/at2819sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023071/at2819Isup2.hkl

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

C22H30O4	Dx = 1.142 Mg m−3
Mr = 358.46	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/a	Cell parameters from 3994 reflections
Hall symbol: -I 4ad	θ = 3.0–25.5°
a = 13.4289 (8) Å	µ = 0.08 mm−1
c = 23.127 (3) Å	T = 291 K
V = 4170.5 (6) Å3	Block, colourless
Z = 8	0.49 × 0.49 × 0.38 mm
F(000) = 1552

Bruker APEXII CCD area-detector diffractometer	1938 independent reflections
Radiation source: fine-focus sealed tube	1542 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→15
Tmin = 0.963, Tmax = 0.972	k = −15→16
13638 measured reflections	l = −28→27

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0476P)2 + 2.3626P] where P = (Fo2 + 2Fc2)/3
1938 reflections	(Δ/σ)max < 0.001
123 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.13 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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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
C1	0.11953 (11)	0.79586 (10)	0.02439 (6)	0.0416 (4)
C2	0.18758 (11)	0.87570 (10)	0.02195 (6)	0.0416 (4)
C3	0.16557 (11)	0.95179 (11)	−0.01654 (6)	0.0431 (4)
H3	0.2085	1.0060	−0.0188	0.052*
C4	0.08231 (11)	0.95010 (10)	−0.05172 (6)	0.0408 (3)
C5	0.01714 (11)	0.87114 (10)	−0.04926 (6)	0.0417 (4)
H5	−0.0385	0.8696	−0.0732	0.050*
C6	0.03503 (10)	0.79350 (10)	−0.01059 (6)	0.0387 (3)
C7	0.28338 (12)	0.87786 (13)	0.05857 (7)	0.0546 (4)
C8	0.34307 (17)	0.97382 (18)	0.04844 (11)	0.0950 (8)
H8A	0.3018	1.0305	0.0566	0.142*
H8B	0.3647	0.9764	0.0089	0.142*
H8C	0.4001	0.9746	0.0735	0.142*
C9	0.34957 (16)	0.78944 (19)	0.04258 (11)	0.0878 (7)
H9A	0.4062	0.7876	0.0679	0.132*
H9B	0.3718	0.7964	0.0033	0.132*
H9C	0.3123	0.7288	0.0465	0.132*
C10	0.25901 (15)	0.87337 (17)	0.12326 (8)	0.0725 (6)
H10A	0.2230	0.9322	0.1342	0.109*
H10B	0.3197	0.8695	0.1451	0.109*
H10C	0.2190	0.8157	0.1310	0.109*
C11	0.00097 (17)	1.02543 (14)	−0.13233 (9)	0.0733 (6)
H11A	0.0167	0.9698	−0.1567	0.110*
H11B	0.0028	1.0856	−0.1547	0.110*
H11C	−0.0644	1.0168	−0.1163	0.110*
O1	0.07070 (9)	1.03143 (8)	−0.08749 (5)	0.0586 (3)
O2	0.13978 (10)	0.72001 (8)	0.06230 (6)	0.0665 (4)
H2	0.0997	0.6747	0.0574	0.100*

	U11	U22	U33	U12	U13	U23
C1	0.0462 (8)	0.0351 (7)	0.0437 (8)	−0.0028 (6)	−0.0020 (6)	0.0010 (6)
C2	0.0421 (8)	0.0389 (8)	0.0438 (8)	−0.0058 (6)	−0.0027 (6)	−0.0030 (6)
C3	0.0453 (8)	0.0369 (8)	0.0470 (8)	−0.0119 (6)	0.0005 (7)	−0.0021 (6)
C4	0.0483 (8)	0.0313 (7)	0.0427 (8)	−0.0033 (6)	−0.0002 (6)	0.0021 (6)
C5	0.0409 (8)	0.0403 (8)	0.0440 (8)	−0.0042 (6)	−0.0047 (6)	−0.0015 (6)
C6	0.0393 (8)	0.0338 (7)	0.0428 (8)	−0.0048 (6)	0.0025 (6)	−0.0024 (6)
C7	0.0491 (9)	0.0582 (10)	0.0565 (10)	−0.0083 (8)	−0.0133 (8)	−0.0002 (8)
C8	0.0763 (14)	0.1044 (17)	0.1042 (18)	−0.0472 (13)	−0.0422 (13)	0.0238 (14)
C9	0.0574 (12)	0.1129 (18)	0.0930 (16)	0.0194 (12)	−0.0211 (11)	−0.0159 (14)
C10	0.0739 (13)	0.0843 (14)	0.0595 (11)	−0.0043 (10)	−0.0228 (10)	−0.0031 (10)
C11	0.0946 (15)	0.0568 (11)	0.0686 (12)	−0.0020 (10)	−0.0309 (11)	0.0131 (9)
O1	0.0791 (8)	0.0406 (6)	0.0562 (7)	−0.0134 (5)	−0.0178 (6)	0.0115 (5)
O2	0.0759 (9)	0.0465 (7)	0.0770 (9)	−0.0174 (6)	−0.0289 (7)	0.0210 (6)

C1—O2	1.3711 (18)	C8—H8A	0.9600
C1—C6	1.394 (2)	C8—H8B	0.9600
C1—C2	1.410 (2)	C8—H8C	0.9600
C2—C3	1.387 (2)	C9—H9A	0.9600
C2—C7	1.541 (2)	C9—H9B	0.9600
C3—C4	1.383 (2)	C9—H9C	0.9600
C3—H3	0.9300	C10—H10A	0.9600
C4—C5	1.3761 (19)	C10—H10B	0.9600
C4—O1	1.3788 (17)	C10—H10C	0.9600
C5—C6	1.395 (2)	C11—O1	1.400 (2)
C5—H5	0.9300	C11—H11A	0.9600
C6—C6i	1.500 (3)	C11—H11B	0.9600
C7—C9	1.529 (3)	C11—H11C	0.9600
C7—C10	1.533 (3)	O2—H2	0.8200
C7—C8	1.535 (3)
O2—C1—C6	121.03 (13)	C7—C8—H8B	109.5
O2—C1—C2	117.52 (13)	H8A—C8—H8B	109.5
C6—C1—C2	121.45 (13)	C7—C8—H8C	109.5
C3—C2—C1	116.61 (13)	H8A—C8—H8C	109.5
C3—C2—C7	121.12 (13)	H8B—C8—H8C	109.5
C1—C2—C7	122.25 (13)	C7—C9—H9A	109.5
C4—C3—C2	122.53 (13)	C7—C9—H9B	109.5
C4—C3—H3	118.7	H9A—C9—H9B	109.5
C2—C3—H3	118.7	C7—C9—H9C	109.5
C5—C4—O1	124.28 (13)	H9A—C9—H9C	109.5
C5—C4—C3	120.16 (13)	H9B—C9—H9C	109.5
O1—C4—C3	115.55 (12)	C7—C10—H10A	109.5
C4—C5—C6	119.54 (13)	C7—C10—H10B	109.5
C4—C5—H5	120.2	H10A—C10—H10B	109.5
C6—C5—H5	120.2	C7—C10—H10C	109.5
C1—C6—C5	119.70 (12)	H10A—C10—H10C	109.5
C1—C6—C6i	121.90 (13)	H10B—C10—H10C	109.5
C5—C6—C6i	118.31 (12)	O1—C11—H11A	109.5
C9—C7—C10	109.25 (17)	O1—C11—H11B	109.5
C9—C7—C8	108.15 (18)	H11A—C11—H11B	109.5
C10—C7—C8	107.07 (16)	O1—C11—H11C	109.5
C9—C7—C2	109.75 (14)	H11A—C11—H11C	109.5
C10—C7—C2	110.95 (14)	H11B—C11—H11C	109.5
C8—C7—C2	111.58 (14)	C4—O1—C11	118.33 (12)
C7—C8—H8A	109.5	C1—O2—H2	109.5
O2—C1—C2—C3	−179.81 (14)	O2—C1—C6—C6i	−2.8 (2)
C6—C1—C2—C3	0.6 (2)	C2—C1—C6—C6i	176.75 (13)
O2—C1—C2—C7	1.9 (2)	C4—C5—C6—C1	−1.1 (2)
C6—C1—C2—C7	−177.67 (14)	C4—C5—C6—C6i	−177.55 (13)
C1—C2—C3—C4	−1.0 (2)	C3—C2—C7—C9	−117.04 (18)
C7—C2—C3—C4	177.31 (14)	C1—C2—C7—C9	61.1 (2)
C2—C3—C4—C5	0.3 (2)	C3—C2—C7—C10	122.12 (17)
C2—C3—C4—O1	179.81 (14)	C1—C2—C7—C10	−59.7 (2)
O1—C4—C5—C6	−178.71 (14)	C3—C2—C7—C8	2.8 (2)
C3—C4—C5—C6	0.7 (2)	C1—C2—C7—C8	−179.02 (17)
O2—C1—C6—C5	−179.17 (14)	C5—C4—O1—C11	−13.7 (2)
C2—C1—C6—C5	0.4 (2)	C3—C4—O1—C11	166.78 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ii	0.82	2.08	2.7592 (15)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	2.08	2.7592 (15)	140

Symmetry code: (i) .