2,3-Dihydro-1H-cyclo­penta­[b]naph­tha­len-1-ol

Ísmail Çelik; Mehmet Akkurt; Ahmet Tutar; Ramazan Erenler; Santiago García-Granda

doi:10.1107/S1600536812005181

. 2012 Feb 10;68(Pt 3):o687. doi: 10.1107/S1600536812005181

2,3-Dihydro-1H-cyclopenta[b]naphthalen-1-ol

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

PMCID: PMC3295469 PMID: 22412580

Abstract

In the title compound, C₁₃H₁₂O, the cyclopentene ring fused with the naphthalene group adopts an envelope conformation. The cyclopentene torsion angle, with the fusion bond at the centre, has a magnitude of 1.16 (16)°. In the crystal, neighbouring molecules are connected through O—H⋯O hydrogen bonds into an R ₄ ⁴(8) ring motif. The crystal packing also features weak π–π stacking interactions [centroid–centroid distance = 3.8981 (8) Å] and C—H⋯π interactions.

Related literature

For the synthesis of the title compound, see: Carpino & Lin (1990 ▶). For the crystal structure of a similar compound, see: Çelik et al. (2009 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₃H₁₂O
M _r = 184.23
Tetragonal,
a = 25.3105 (4) Å
c = 6.0995 (2) Å
V = 3907.47 (18) Å³
Z = 16
Cu Kα radiation
μ = 0.61 mm⁻¹
T = 299 K
0.46 × 0.17 × 0.11 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.884, T _max = 0.936
5702 measured reflections
1791 independent reflections
1580 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.126
S = 1.04
1791 reflections
131 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.10 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005181/qm2052sup1.cif

e-68-0o687-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005181/qm2052Isup2.hkl

e-68-0o687-Isup2.hkl^{(88.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812005181/qm2052Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O1ⁱ	0.93 (2)	1.78 (2)	2.7113 (15)	174.4 (18)
C3—H3⋯Cg2ⁱⁱ	0.93	2.71	3.633 (2)	171
C11—H11A⋯Cg2ⁱⁱⁱ	0.97	2.89	3.706 (2)	142

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

supplementary crystallographic information

Comment

The treatment of benz[f]indanone with sodium borohydride in THF/MeOH for 2 h afforded the corresponding benz[f]indan-1-ol in an 89% yield (Carpino & Lin, 1990). Two signal groups, aliphatic and aromatic were observed in ¹H-NMR spectra. The H2 and H3 protons exhibited a AA'BB' splitting pattern. H1 appeared at lower magnetic field than the 2,3 H atoms. This is due to the electronegativity of oxygen atom attached to C-1. The signal observed at δ 5.39 as a broad singlet could be attributed to OH group. Moreover a thirteen line ¹³C-NMR spectrum supports the proposed structure. The exact configuration of the molecule was established by X-ray diffraction.

The molecular structure of the title compound (I) is shown in Fig. 1. All bond lengths and angles in the title compound (I) show normal values (Allen et al., 1987; Çelik et al., 2009). The cyclopentene ring (C8–C9/C11–C13) fused with the naphthalene group (C1–C10) adopts an envelope conformation [puckering parameters: Q(2) = 0.2503 (18) Å, φ(2) = 110.1 (4)°; (Cremer & Pople, 1975)] with atom C12 deviating from the ring plane. The naphthalene group is essentially planar with a maximum deviation of -0.013 (1) Å for C8. The torsion angles C9–C8–C13–O1 and C7–C8– C13–O1 are -141.52 (12) and 38.33 (19) °, respectively.

In the crystal, neighbouring molecules are linked with intermolecular O—H···O hydrogen bonds, forming R₄⁴(8) ring motifs (Bernstein et al., 1995). A weak π -π stacking interaction [Cg3···Cg3ⁱⁱⁱ = 3.8981 (8) Å (symmetry code: (iii) = -x, -y, -z)] between the C5–C10 benzene rings and two C—H···π interactions contribute to the stabilization of the crystal packing.

Experimental

To an ice-cold, stirred solution of benz[f]indanone (4.0 g, 22 mmol) in THF/MeOH (30/20 ml) mixture was added NaBH₄ (0.34 g, 8.8 mmol). The reaction mixture was allowed to warm to room temperature. After the completion of the reaction, 2 h, water was added to the reaction mixture which was extracted with diethyl ether (3×50 ml), dried over MgSO₄ and concentrated in vacuo affording benz[f]indan-1-ol which was crystallized from hexane/chloroform as yellow needles (3.6 g, 89%). ¹H-NMR (400 MHz, CDCl₃): δ 2.0–2.09 (m, 2H, H2), 2.54–2.60 (m, 1H, H3), 2.94–3.02 (m, 1H, H3'), 3.18–3.26 (m, 1H, H1), 5.39 (brs, 1H, OH), 7.43–7.49 (m, 2H, ArH), 7.70 (brs, 1H, ArH), 7.80–7.85 (brs, 2H, ArH), 7.87 (brs, 1H, ArH); ¹³C-NMR (100 MHz, CDCl₃): δ 29.3, 36.6, 75.9, 122.7, 122.9, 125.2, 125.8, 127.6, 128.2, 132.9, 133.9, 141.5, 144.3.