2,3,4,5,6-Penta-bromo-phenol.

The title compound, C(6)HBr(5)O, is the perbrominated derivative of phenol. The mol-ecule shows non-crystallographic mirror symmetry. Bond lengths between the C and Br atoms are normal. In the crystal structure, O-H⋯O hydrogen bonds connect the mol-ecules into infinite strands. Dispersive Br⋯Br contacts are observed. No significant π-π stacking is obvious.

Related literature

For the structure of the perfluorinated derivative of phenol, see: Das et al. (2006 ▶); Gdaniec (2007 ▶). For the structure of 2,3,4,5,6-penta­chloro­phenol, see: Sakurai (1962 ▶).

Experimental

Crystal data

C6HBr5O

M = 488.57

Monoclinic,

a = 32.3058 (15) Å

b = 3.9957 (2) Å

c = 16.1887 (8) Å

β = 112.118 (3)°

V = 1935.93 (17) Å3

Z = 8

Mo Kα radiation

μ = 20.70 mm−1

T = 200 (2) K

0.28 × 0.08 × 0.05 mm

Data collection

Nonius Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.062, T max = 0.355

13465 measured reflections

2219 independent reflections

1930 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.074

S = 1.03

2219 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.88 e Å−3

Δρmin = −1.02 e Å−3

Data collection: COLLECT (Nonius, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor 1997 ▶); data reduction: DENZO (Otwinowski & Minor 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028602/rk2109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808028602/rk2109Isup2.hkl

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

C6HBr5O	F(000) = 1760
Mr = 488.57	Dx = 3.353 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8265 reflections
a = 32.3058 (15) Å	θ = 3.1–27.5°
b = 3.9957 (2) Å	µ = 20.70 mm−1
c = 16.1887 (8) Å	T = 200 K
β = 112.118 (3)°	Rod, colourless
V = 1935.93 (17) Å3	0.28 × 0.08 × 0.05 mm
Z = 8

Nonius Kappa CCD diffractometer	2219 independent reflections
Radiation source: Rotating anode	1930 reflections with I > 2σ(I)
MONTEL, graded multilayered X-ray optics	Rint = 0.054
Rotation images; thick slices scans	θmax = 27.6°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −41→41
Tmin = 0.062, Tmax = 0.355	k = −4→5
13465 measured reflections	l = −21→21

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)] = 0.030	H-atom parameters constrained
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0374P)2 + 5.8817P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2219 reflections	Δρmax = 0.88 e Å−3
111 parameters	Δρmin = −1.02 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00087 (8)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.204848 (13)	0.51248 (10)	0.41077 (2)	0.03029 (14)
Br2	0.096769 (13)	0.38703 (10)	0.36125 (2)	0.02821 (13)
Br3	0.024427 (13)	0.61492 (11)	0.16493 (3)	0.03106 (14)
Br4	0.060474 (12)	0.97946 (11)	0.02144 (2)	0.02709 (13)
Br5	0.169251 (13)	1.09979 (10)	0.07733 (2)	0.02651 (13)
O1	0.22213 (8)	0.8423 (7)	0.26447 (18)	0.0289 (6)
H1	0.2271	0.9643	0.2270	0.043*
C1	0.17732 (11)	0.7978 (9)	0.2394 (2)	0.0213 (7)
C2	0.16196 (12)	0.6421 (9)	0.2996 (2)	0.0216 (7)
C3	0.11662 (12)	0.5889 (9)	0.2773 (2)	0.0211 (7)
C4	0.08601 (11)	0.6883 (9)	0.1945 (2)	0.0213 (7)
C5	0.10107 (12)	0.8416 (8)	0.1339 (2)	0.0209 (7)
C6	0.14663 (12)	0.8957 (8)	0.1567 (2)	0.0197 (7)

	U11	U22	U33	U12	U13	U23
Br1	0.0248 (2)	0.0387 (3)	0.0229 (2)	0.00504 (16)	0.00385 (16)	0.00541 (16)
Br2	0.0300 (2)	0.0331 (2)	0.0244 (2)	−0.00243 (15)	0.01352 (16)	0.00349 (14)
Br3	0.0171 (2)	0.0443 (3)	0.0318 (2)	−0.00324 (15)	0.00924 (16)	0.00412 (16)
Br4	0.0201 (2)	0.0377 (2)	0.0212 (2)	0.00309 (15)	0.00524 (15)	0.00423 (14)
Br5	0.0238 (2)	0.0331 (2)	0.0255 (2)	−0.00301 (14)	0.01252 (16)	0.00230 (14)
O1	0.0160 (12)	0.0393 (16)	0.0315 (14)	0.0005 (11)	0.0091 (11)	0.0025 (12)
C1	0.0146 (16)	0.0222 (16)	0.0260 (17)	−0.0013 (14)	0.0066 (13)	−0.0031 (14)
C2	0.0188 (18)	0.0236 (18)	0.0201 (16)	0.0003 (14)	0.0048 (13)	−0.0015 (13)
C3	0.0237 (19)	0.0211 (16)	0.0208 (17)	−0.0001 (13)	0.0110 (14)	−0.0028 (13)
C4	0.0146 (16)	0.0261 (17)	0.0244 (17)	−0.0029 (14)	0.0087 (13)	−0.0038 (14)
C5	0.0196 (17)	0.0237 (17)	0.0184 (15)	−0.0001 (14)	0.0061 (13)	−0.0027 (13)
C6	0.0213 (17)	0.0215 (17)	0.0207 (16)	−0.0026 (14)	0.0129 (13)	−0.0009 (13)

Br1—C2	1.884 (3)	C1—C6	1.389 (5)
Br2—C3	1.888 (4)	C1—C2	1.395 (5)
Br3—C4	1.886 (3)	C2—C3	1.387 (5)
Br4—C5	1.882 (3)	C3—C4	1.391 (5)
Br5—C6	1.886 (4)	C4—C5	1.390 (5)
O1—C1	1.360 (4)	C5—C6	1.393 (5)
O1—H1	0.8400
C1—O1—H1	109.5	C5—C4—C3	119.7 (3)
O1—C1—C6	122.9 (3)	C5—C4—Br3	120.4 (2)
O1—C1—C2	117.9 (3)	C3—C4—Br3	120.0 (3)
C6—C1—C2	119.1 (3)	C4—C5—C6	119.8 (3)
C3—C2—C1	120.3 (3)	C4—C5—Br4	120.7 (3)
C3—C2—Br1	122.1 (3)	C6—C5—Br4	119.5 (3)
C1—C2—Br1	117.6 (3)	C1—C6—C5	120.7 (3)
C2—C3—C4	120.4 (3)	C1—C6—Br5	117.4 (3)
C2—C3—Br2	119.3 (3)	C5—C6—Br5	121.9 (3)
C4—C3—Br2	120.3 (3)
O1—C1—C2—C3	−179.7 (3)	C3—C4—C5—C6	−0.2 (5)
C6—C1—C2—C3	−0.6 (5)	Br3—C4—C5—C6	179.7 (3)
O1—C1—C2—Br1	0.7 (4)	C3—C4—C5—Br4	−179.9 (3)
C6—C1—C2—Br1	179.8 (3)	Br3—C4—C5—Br4	0.1 (4)
C1—C2—C3—C4	0.4 (5)	O1—C1—C6—C5	179.4 (3)
Br1—C2—C3—C4	180.0 (3)	C2—C1—C6—C5	0.4 (5)
C1—C2—C3—Br2	−178.5 (3)	O1—C1—C6—Br5	−0.2 (5)
Br1—C2—C3—Br2	1.1 (4)	C2—C1—C6—Br5	−179.2 (3)
C2—C3—C4—C5	0.0 (5)	C4—C5—C6—C1	0.0 (5)
Br2—C3—C4—C5	178.9 (3)	Br4—C5—C6—C1	179.7 (3)
C2—C3—C4—Br3	−179.9 (3)	C4—C5—C6—Br5	179.6 (3)
Br2—C3—C4—Br3	−1.1 (4)	Br4—C5—C6—Br5	−0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1i	0.84	2.19	2.844 (4)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1i	0.84	2.19	2.844 (4)	134

Symmetry code: (i) .