2,4-Dibromo-6-tert-butyl-benzene-1,3-diol.

In the title compound, C(10)H(12)Br(2)O(2), a multiply substituted bromo-arene, the C-C-C angles within the aromatic ring are in the range 115.7 (7)-122.4 (7)°. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, but no π-π stacking is observed.

Related literature

For similar compounds, see: Butler & Walker (1993 ▶); Seevers & Counsell (1982 ▶); Zheng et al. (2004 ▶).

Experimental

Crystal data

C10H12Br2O2

M = 324.02

Tetragonal,

a = 11.618 (3) Å

c = 17.761 (4) Å

V = 2397.4 (9) Å3

Z = 8

Mo Kα radiation

μ = 6.74 mm−1

T = 290 K

0.22 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.319, T max = 0.346

4935 measured reflections

1367 independent reflections

775 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.059

S = 1.08

1367 reflections

132 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034866/vm2103sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034866/vm2103Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034866/vm2103Isup3.cml

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

C10H12Br2O2	Dx = 1.795 Mg m−3
Mr = 324.02	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4b2	Cell parameters from 1414 reflections
Hall symbol: P -4 -2ab	θ = 3.4–29.0°
a = 11.618 (3) Å	µ = 6.74 mm−1
c = 17.761 (4) Å	T = 290 K
V = 2397.4 (9) Å3	Prismatic, colorless
Z = 8	0.22 × 0.20 × 0.20 mm
F(000) = 1264

Oxford Diffraction Xcalibur Eos Gemini diffractometer	1367 independent reflections
Radiation source: fine-focus sealed tube	775 reflections with I > 2σ(I)
graphite	Rint = 0.087
Detector resolution: 16.2312 pixels mm-1	θmax = 26.4°, θmin = 3.4°
ω scans	h = −7→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→11
Tmin = 0.319, Tmax = 0.346	l = −22→11
4935 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0056P)2] where P = (Fo2 + 2Fc2)/3
1367 reflections	(Δ/σ)max < 0.001
132 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Experimental. CrysAlisPro (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Br1	0.54152 (12)	0.82654 (10)	0.57359 (5)	0.1038 (5)
Br2	0.26935 (9)	0.44073 (9)	0.65318 (6)	0.0780 (4)
O1	0.5347 (6)	0.8647 (5)	0.7424 (3)	0.076 (2)
H1	0.5215	0.9175	0.7131	0.114*
O2	0.4052 (6)	0.6107 (6)	0.5499 (2)	0.085 (2)
H2	0.4250	0.5434	0.5444	0.128*
C1	0.4723 (7)	0.7689 (7)	0.7214 (4)	0.045 (2)
C2	0.4666 (7)	0.7357 (7)	0.6471 (4)	0.058 (2)
C3	0.4069 (7)	0.6383 (8)	0.6250 (4)	0.055 (3)
C4	0.3557 (7)	0.5756 (6)	0.6803 (5)	0.050 (2)
C5	0.3603 (7)	0.6096 (7)	0.7559 (4)	0.047 (2)
H5	0.3220	0.5655	0.7917	0.056*
C6	0.4188 (7)	0.7050 (7)	0.7788 (4)	0.046 (2)
C7	0.4255 (8)	0.7422 (9)	0.8617 (4)	0.065 (3)
C8	0.3682 (9)	0.8603 (8)	0.8714 (4)	0.090 (4)
H8A	0.2916	0.8579	0.8512	0.134*
H8B	0.4123	0.9176	0.8452	0.134*
H8C	0.3648	0.8794	0.9240	0.134*
C9	0.5530 (9)	0.7473 (11)	0.8882 (5)	0.121 (4)
H9A	0.5558	0.7698	0.9402	0.182*
H9B	0.5943	0.8024	0.8583	0.182*
H9C	0.5877	0.6728	0.8825	0.182*
C10	0.3623 (9)	0.6572 (8)	0.9131 (4)	0.093 (3)
H10A	0.3963	0.5822	0.9082	0.139*
H10B	0.2827	0.6536	0.8990	0.139*
H10C	0.3684	0.6825	0.9644	0.139*

	U11	U22	U33	U12	U13	U23
Br1	0.1535 (13)	0.0852 (10)	0.0726 (6)	−0.0324 (7)	0.0515 (8)	0.0131 (6)
Br2	0.0772 (8)	0.0694 (8)	0.0875 (7)	−0.0210 (6)	0.0110 (7)	−0.0109 (6)
O1	0.080 (6)	0.068 (5)	0.079 (4)	−0.032 (5)	0.013 (3)	−0.007 (3)
O2	0.130 (7)	0.084 (6)	0.041 (3)	−0.009 (5)	0.028 (3)	−0.012 (3)
C1	0.049 (6)	0.037 (6)	0.050 (4)	−0.005 (4)	0.010 (5)	0.001 (4)
C2	0.070 (7)	0.054 (6)	0.049 (5)	−0.013 (5)	0.023 (5)	0.002 (5)
C3	0.070 (7)	0.053 (7)	0.043 (5)	−0.009 (5)	0.019 (5)	0.011 (5)
C4	0.047 (6)	0.026 (5)	0.076 (6)	−0.007 (4)	0.009 (5)	−0.004 (4)
C5	0.038 (6)	0.060 (7)	0.041 (5)	0.003 (5)	0.011 (4)	0.013 (5)
C6	0.047 (6)	0.048 (6)	0.044 (4)	−0.002 (5)	0.010 (4)	0.012 (5)
C7	0.067 (7)	0.084 (8)	0.046 (5)	−0.005 (6)	0.000 (5)	0.007 (5)
C8	0.120 (11)	0.094 (10)	0.055 (6)	0.009 (7)	0.022 (6)	−0.011 (5)
C9	0.108 (11)	0.162 (13)	0.094 (7)	−0.020 (8)	−0.047 (7)	0.023 (7)
C10	0.112 (11)	0.112 (10)	0.054 (6)	−0.013 (7)	0.006 (6)	0.009 (6)

Br1—C2	1.891 (7)	C6—C7	1.536 (10)
Br2—C4	1.922 (7)	C7—C10	1.532 (11)
O1—C1	1.379 (8)	C7—C8	1.536 (11)
O1—H1	0.8200	C7—C9	1.556 (11)
O2—C3	1.373 (8)	C8—H8A	0.9600
O2—H2	0.8200	C8—H8B	0.9600
C1—C2	1.377 (9)	C8—H8C	0.9600
C1—C6	1.406 (9)	C9—H9A	0.9600
C2—C3	1.384 (10)	C9—H9B	0.9600
C3—C4	1.360 (10)	C9—H9C	0.9600
C4—C5	1.400 (9)	C10—H10A	0.9600
C5—C6	1.362 (10)	C10—H10B	0.9600
C5—H5	0.9300	C10—H10C	0.9600
C1—O1—H1	109.5	C6—C7—C8	109.7 (6)
C3—O2—H2	109.5	C10—C7—C9	107.5 (7)
C2—C1—O1	120.7 (7)	C6—C7—C9	110.4 (7)
C2—C1—C6	121.7 (7)	C8—C7—C9	110.2 (10)
O1—C1—C6	117.5 (7)	C7—C8—H8A	109.5
C1—C2—C3	121.6 (7)	C7—C8—H8B	109.5
C1—C2—Br1	118.9 (6)	H8A—C8—H8B	109.5
C3—C2—Br1	119.5 (5)	C7—C8—H8C	109.5
C4—C3—O2	124.7 (8)	H8A—C8—H8C	109.5
C4—C3—C2	117.0 (7)	H8B—C8—H8C	109.5
O2—C3—C2	118.3 (7)	C7—C9—H9A	109.5
C3—C4—C5	121.6 (7)	C7—C9—H9B	109.5
C3—C4—Br2	119.0 (6)	H9A—C9—H9B	109.5
C5—C4—Br2	119.4 (6)	C7—C9—H9C	109.5
C6—C5—C4	122.4 (7)	H9A—C9—H9C	109.5
C6—C5—H5	118.8	H9B—C9—H9C	109.5
C4—C5—H5	118.8	C7—C10—H10A	109.5
C5—C6—C1	115.7 (7)	C7—C10—H10B	109.5
C5—C6—C7	122.7 (7)	H10A—C10—H10B	109.5
C1—C6—C7	121.6 (8)	C7—C10—H10C	109.5
C10—C7—C6	111.5 (8)	H10A—C10—H10C	109.5
C10—C7—C8	107.5 (7)	H10B—C10—H10C	109.5
O1—C1—C2—C3	178.4 (9)	Br2—C4—C5—C6	−179.3 (7)
C6—C1—C2—C3	0.7 (14)	C4—C5—C6—C1	1.4 (13)
O1—C1—C2—Br1	−2.1 (12)	C4—C5—C6—C7	−179.3 (7)
C6—C1—C2—Br1	−179.8 (7)	C2—C1—C6—C5	−0.8 (13)
C1—C2—C3—C4	−1.1 (13)	O1—C1—C6—C5	−178.6 (8)
Br1—C2—C3—C4	179.4 (6)	C2—C1—C6—C7	179.9 (8)
C1—C2—C3—O2	−180.0 (8)	O1—C1—C6—C7	2.1 (12)
Br1—C2—C3—O2	0.5 (12)	C5—C6—C7—C10	1.8 (12)
O2—C3—C4—C5	−179.5 (7)	C1—C6—C7—C10	−178.9 (8)
C2—C3—C4—C5	1.7 (12)	C5—C6—C7—C8	−117.2 (10)
O2—C3—C4—Br2	−2.2 (12)	C1—C6—C7—C8	62.1 (11)
C2—C3—C4—Br2	179.0 (7)	C5—C6—C7—C9	121.2 (10)
C3—C4—C5—C6	−2.0 (13)	C1—C6—C7—C9	−59.5 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1i	0.82	2.67	3.246 (13)	129.
O2—H2···O2ii	0.82	2.36	2.979 (9)	133.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1i	0.82	2.67	3.246 (13)	129
O2—H2⋯O2ii	0.82	2.36	2.979 (9)	133

Symmetry codes: (i) ; (ii) .