2,5-Dibromo­indan-1-ol

Çelik, Í.; Akkurt, M.; Yilmaz, M.; Tutar, A.; Erenler, R.; García-Granda, S.

doi:10.1107/S1600536812035829

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages o2795-o2796

doi:10.1107/S1600536812035829

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2,5-Dibromoindan-1-ol

Ísmail Çelik,^a ^* Mehmet Akkurt,^b Makbule Yilmaz,^c Ahmet Tutar,^d Ramazan Erenler ^e and Santiago García-Granda ^f

^aDepartment of Physics, Faculty of Sciences, Cumhuriyet University, 58140 Sivas, Turkey, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 39039 Kayseri, Turkey, ^cDuzce University, Faculty of Art and Science, Department of Chemistry, TR-81620 Duzce, Turkey, ^dSakarya University, Faculty of Art and Science, Department of Chemistry, TR-54187 Adapazarı, Turkey, ^eGaziosmanpasa University, Faculty of Art and Science, Department of Chemistry, TR-60240 Tokat, Turkey, and ^fDepartamento Química Física y Analítica, Facultad de Química, Universidad Oviedo, C/ Julián Clavería, 8, 33006 Oviedo (Asturias), Spain
^*Correspondence e-mail: icelik@cumhuriyet.edu.tr

(Received 10 August 2012; accepted 14 August 2012; online 25 August 2012)

In the title compound, C₉H₈Br₂O, the cyclopentene ring adopts an envelope conformation with the brominated C atom as the flap. In the crystal, molecules are linked by strong O—H⋯O hydrogen bonds into zigzag C(4) chains along [010]. In addition, a C—H⋯π interaction involving the benzene ring and the H atom attached to the hydroxylated 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_r = 291.95
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.082
wR(F²) = 0.228
S = 1.00
1777 reflections
79 parameters
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.78 e Å⁻³

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) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y-1, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812035829/pk2441sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812035829/pk2441Isup3.cml

checkCIF report

Comment top

Bromination of hydrocarbons are important processes in synthetic chemistry (Cakmak et al., 2006; Erenler et al., 2006; Erenler & Cakmak, 2004). Indanes are an important class of molecules due to their pharmacological and medicinal proparties (Mitrochkine et al., 1995; Catto et al., 2010; Wu, 2006; McClure et al., 2011) as well as in natural product chemistry (Snyder & Brill, 2011).

In the title compound (I), (Fig. 1), the five-membered C1/C6–C9 cyclopentene ring exhibits an envelope conformation with C8 at the tip of the envelope [the puckering parameters (Cremer & Pople, 1975) are Q(2) = 0.289 (17) Å and ϕ(2) = 290 (3) °]. All bond lengths and bond angles in (I) are in the normal range and are in good agreement with those reported in a similar structure (Çelik et al., 2012).

In the crystal, pairs of strong O—H···O hydrogen bonds connect the molecules, forming zigzag C(4) chains propagating along the b axis (Bernstein et al., 1995; Table 1, Fig. 2). In addition, a C—H···π interaction with the benzene ring is also found (Table 1).

Related literature top

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 top

To a stirred solution of tribromide (1.0 g, 2.8 mmol) in THF (10 ml) was added a solution of AgClO₄.H₂O (0.82 g, 3.64 mmol) in aqueous THF (5 ml THF / 2 ml H₂O). The resulting mixture was stirred at room temperature for 6 h. The precipitated AgBr was removed by filtration and then the solution was dried over calcium chloride. After removal of the solvent, the residue was purified by silica gel column chromatography. Elution with hexane/ethyl acetate (4:1) afforded the 2,5-dibromo-1-hdyroxylindane (0.59 g, 72%).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).

Figures top

An ORTEP plot of (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

View of the packing and hydrogen bonding of (I), along the a axis. H atoms not involved in hydrogen bonding are omitted for the sake of clarity.

2,5-Dibromoindan-1-ol top

Crystal data top

C₉H₈Br₂O	F(000) = 560
M_r = 291.95	D_x = 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

Data collection top

Agilent Xcalibur Ruby Gemini diffractometer	1777 independent reflections
Radiation source: Enhance (Cu) X-ray Source	733 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.0000
Detector resolution: 10.2673 pixels mm^-1	θ_max = 70.6°, θ_min = 4.4°
ω scans	h = −11→11
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	k = 0→5
T_min = 0.882, T_max = 0.900	l = 0→24
1777 measured reflections

Refinement top

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(F_o²) + (0.0341P)²] where P = (F_o² + 2F_c²)/3
1777 reflections	(Δ/σ)_max < 0.001
79 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.78 e Å⁻³

Crystal data top

C₉H₈Br₂O	V = 941.3 (2) Å³
M_r = 291.95	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 9.5137 (10) Å	µ = 10.50 mm⁻¹
b = 4.8991 (7) Å	T = 299 K
c = 20.249 (3) Å	0.17 × 0.01 × 0.01 mm
β = 94.165 (10)°

Data collection top

Agilent Xcalibur Ruby Gemini diffractometer	1777 independent reflections
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	733 reflections with I > 2σ(I)
T_min = 0.882, T_max = 0.900	R_int = 0.0000
1777 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.228	H-atom parameters constrained
S = 1.00	Δρ_max = 0.68 e Å⁻³
1777 reflections	Δρ_min = −0.78 e Å⁻³
79 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, y−1/2, −z+3/2; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₉H₈Br₂O
M_r	291.95
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	9.5137 (10), 4.8991 (7), 20.249 (3)
β (°)	94.165 (10)
V (Å³)	941.3 (2)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	10.50
Crystal size (mm)	0.17 × 0.01 × 0.01

Data collection
Diffractometer	Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction	Part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)
T_min, T_max	0.882, 0.900
No. of measured, independent and observed [I > 2σ(I)] reflections	1777, 1777, 733
R_int	0.0000
(sin θ/λ)_max (Å⁻¹)	0.612

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.228, 1.00
No. of reflections	1777
No. of parameters	79
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.78

Computer programs: CrysAlis PRO (Agilent, 2011), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1999), WinGX (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+2, y−1/2, −z+3/2; (ii) x, y−1, z.

References

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Volume 68| Part 9| September 2012| Pages o2795-o2796

doi:10.1107/S1600536812035829

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