2,5-Dibromo-indan-1-ol.

In the title compound, C(9)H(8)Br(2)O, the cyclo-pentene ring adopts an envelope conformation with the brominated C atom as the flap. In the crystal, mol-ecules are linked by strong O-H⋯O hydrogen bonds into zigzag C(4) chains along [010]. In addition, a C-H⋯π inter-action involving the benzene ring and the H atom attached to the hy-droxy-lated C atom is observed.

Related literature

For bromination of hydro­carbons, see: Cakmak et al. (2006 ▶); Erenler & Cakmak (2004 ▶); Erenler et al. (2006 ▶). For the pharmacological and medicinal proparties of indanes, see: Mitrochkine et al. (1995 ▶); Catto et al. (2010 ▶); Wu (2006 ▶); McClure et al. (2011 ▶) and for their use in natural product chemistry, see: Snyder & Brill (2011 ▶). For a similar structure, see: Çelik et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H8Br2O

M = 291.95

Monoclinic,

a = 9.5137 (10) Å

b = 4.8991 (7) Å

c = 20.249 (3) Å

β = 94.165 (10)°

V = 941.3 (2) Å3

Z = 4

Cu Kα radiation

μ = 10.50 mm−1

T = 299 K

0.17 × 0.01 × 0.01 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: refined from ΔF (XABS2; Parkin et al., 1995 ▶)T min = 0.882, T max = 0.900

1777 measured reflections

1777 independent reflections

733 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.228

S = 1.00

1777 reflections

79 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.78 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035829/pk2441sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035829/pk2441Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035829/pk2441Isup3.cml

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

C9H8Br2O	F(000) = 560
Mr = 291.95	Dx = 2.060 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 378 reflections
a = 9.5137 (10) Å	θ = 4.4–70.4°
b = 4.8991 (7) Å	µ = 10.50 mm−1
c = 20.249 (3) Å	T = 299 K
β = 94.165 (10)°	Prism, colourless
V = 941.3 (2) Å3	0.17 × 0.01 × 0.01 mm
Z = 4

Agilent Xcalibur Ruby Gemini diffractometer	1777 independent reflections
Radiation source: Enhance (Cu) X-ray Source	733 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 10.2673 pixels mm-1	θmax = 70.6°, θmin = 4.4°
ω scans	h = −11→11
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	k = 0→5
Tmin = 0.882, Tmax = 0.900	l = 0→24
1777 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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.228	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0341P)2] where P = (Fo2 + 2Fc2)/3
1777 reflections	(Δ/σ)max < 0.001
79 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.78 e Å−3

Experimental. Absorption correction: XABS2 (Parkin et al., 1995); Quadratic fit to sin(theta)/lambda - 18 parameters

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.4208 (2)	0.8732 (4)	0.60524 (11)	0.0799 (7)
Br2	1.11644 (19)	0.3412 (4)	0.60918 (10)	0.0766 (7)
O1	0.9808 (12)	0.057 (2)	0.7220 (5)	0.069 (4)
C1	0.7790 (16)	0.247 (3)	0.6578 (8)	0.062 (2)
C2	0.7029 (16)	0.359 (3)	0.7090 (8)	0.062 (2)
C3	0.5983 (16)	0.544 (3)	0.6919 (8)	0.062 (2)
C4	0.5687 (16)	0.618 (3)	0.6270 (7)	0.062 (2)
C5	0.6461 (16)	0.517 (3)	0.5754 (8)	0.062 (2)
C6	0.7444 (16)	0.331 (3)	0.5936 (8)	0.062 (2)
C7	0.8485 (19)	0.172 (3)	0.5499 (7)	0.067 (6)
C8	0.9613 (18)	0.074 (3)	0.5978 (7)	0.063 (6)
C9	0.8931 (16)	0.040 (3)	0.6617 (7)	0.057 (5)
H1	1.00390	−0.09700	0.73430	0.1030*
H2	0.72330	0.30880	0.75290	0.0740*
H3	0.54710	0.62080	0.72470	0.0740*
H5	0.62990	0.57520	0.53190	0.0740*
H7A	0.80100	0.02070	0.52700	0.0810*
H7B	0.88630	0.29260	0.51750	0.0810*
H8	0.99730	−0.10210	0.58330	0.0750*
H9	0.84820	−0.14010	0.66060	0.0680*

	U11	U22	U33	U12	U13	U23
Br1	0.0591 (11)	0.0778 (13)	0.1011 (14)	0.0087 (10)	−0.0058 (10)	0.0030 (11)
Br2	0.0611 (11)	0.0755 (12)	0.0942 (13)	0.0033 (9)	0.0123 (9)	0.0108 (10)
O1	0.081 (8)	0.052 (6)	0.072 (7)	0.005 (6)	−0.002 (6)	0.004 (5)
C1	0.052 (4)	0.069 (4)	0.064 (4)	−0.007 (3)	0.001 (3)	−0.001 (3)
C2	0.052 (4)	0.069 (4)	0.064 (4)	−0.007 (3)	0.001 (3)	−0.001 (3)
C3	0.052 (4)	0.069 (4)	0.064 (4)	−0.007 (3)	0.001 (3)	−0.001 (3)
C4	0.052 (4)	0.069 (4)	0.064 (4)	−0.007 (3)	0.001 (3)	−0.001 (3)
C5	0.052 (4)	0.069 (4)	0.064 (4)	−0.007 (3)	0.001 (3)	−0.001 (3)
C6	0.052 (4)	0.069 (4)	0.064 (4)	−0.007 (3)	0.001 (3)	−0.001 (3)
C7	0.089 (12)	0.058 (9)	0.056 (8)	0.007 (9)	0.013 (8)	−0.005 (8)
C8	0.083 (12)	0.046 (8)	0.058 (9)	0.008 (8)	−0.005 (8)	0.004 (7)
C9	0.059 (9)	0.048 (8)	0.061 (9)	−0.003 (7)	−0.008 (8)	0.010 (7)

Br1—C4	1.910 (15)	C6—C7	1.58 (2)
Br2—C8	1.974 (16)	C7—C8	1.47 (2)
O1—C9	1.430 (18)	C8—C9	1.50 (2)
O1—H1	0.8200	C2—H2	0.9300
C1—C6	1.38 (2)	C3—H3	0.9300
C1—C9	1.48 (2)	C5—H5	0.9300
C1—C2	1.42 (2)	C7—H7A	0.9700
C2—C3	1.37 (2)	C7—H7B	0.9700
C3—C4	1.37 (2)	C8—H8	0.9800
C4—C5	1.41 (2)	C9—H9	0.9800
C5—C6	1.34 (2)
C9—O1—H1	109.00	O1—C9—C1	112.6 (12)
C2—C1—C6	118.3 (14)	C1—C2—H2	121.00
C6—C1—C9	112.2 (13)	C3—C2—H2	121.00
C2—C1—C9	129.5 (14)	C2—C3—H3	120.00
C1—C2—C3	118.1 (15)	C4—C3—H3	120.00
C2—C3—C4	120.7 (15)	C4—C5—H5	122.00
Br1—C4—C5	118.3 (11)	C6—C5—H5	122.00
C3—C4—C5	122.3 (14)	C6—C7—H7A	111.00
Br1—C4—C3	119.4 (11)	C6—C7—H7B	111.00
C4—C5—C6	115.3 (15)	C8—C7—H7A	111.00
C1—C6—C7	105.3 (12)	C8—C7—H7B	111.00
C5—C6—C7	129.4 (14)	H7A—C7—H7B	109.00
C1—C6—C5	125.2 (15)	Br2—C8—H8	110.00
C6—C7—C8	104.4 (12)	C7—C8—H8	110.00
Br2—C8—C9	109.9 (10)	C9—C8—H8	110.00
C7—C8—C9	105.3 (13)	O1—C9—H9	107.00
Br2—C8—C7	111.3 (10)	C1—C9—H9	107.00
O1—C9—C8	117.9 (13)	C8—C9—H9	107.00
C1—C9—C8	103.8 (12)
C6—C1—C2—C3	0 (2)	Br1—C4—C5—C6	−177.5 (11)
C9—C1—C2—C3	−178.1 (15)	C3—C4—C5—C6	4 (2)
C2—C1—C6—C5	2 (2)	C4—C5—C6—C1	−4 (2)
C2—C1—C6—C7	179.4 (13)	C4—C5—C6—C7	179.1 (14)
C9—C1—C6—C5	−179.5 (15)	C1—C6—C7—C8	−16.7 (16)
C9—C1—C6—C7	−1.9 (17)	C5—C6—C7—C8	160.8 (16)
C2—C1—C9—O1	−33 (2)	C6—C7—C8—Br2	−90.7 (12)
C2—C1—C9—C8	−162.1 (15)	C6—C7—C8—C9	28.3 (15)
C6—C1—C9—O1	148.1 (13)	Br2—C8—C9—O1	−34.8 (16)
C6—C1—C9—C8	19.4 (17)	Br2—C8—C9—C1	90.6 (12)
C1—C2—C3—C4	0 (2)	C7—C8—C9—O1	−154.8 (12)
C2—C3—C4—Br1	179.3 (12)	C7—C8—C9—C1	−29.4 (15)
C2—C3—C4—C5	−2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1i	0.82	1.91	2.713 (14)	165
C9—H9···Cg2ii	0.98	2.67	3.629 (16)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1i	0.82	1.91	2.713 (14)	165
C9—H9⋯Cg2ii	0.98	2.67	3.629 (16)	166

Symmetry codes: (i) ; (ii) .