11-Hy­droxy-9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propano­anthracen-12-one

Usama Karama; Abdulrahman I Almansour; Natarajan Arumugam; Ibrahim Abdul Razak; Suhana Arshad

doi:10.1107/S1600536811033538

. 2011 Aug 27;67(Pt 9):o2487. doi: 10.1107/S1600536811033538

11-Hydroxy-9-(prop-2-en-1-yl)-9,10-dihydro-9,10-propanoanthracen-12-one

Usama Karama ^a, Abdulrahman I Almansour ^a, Natarajan Arumugam ^a, Ibrahim Abdul Razak ^b,^*,^‡, Suhana Arshad ^b

PMCID: PMC3200828 PMID: 22059039

Abstract

In the title compound, C₂₀H₁₈O₂, the central six-membered ring adopts a boat conformation and the terminal benzene rings make a dihedral angle of 42.66 (4)° with each other. In the crystal structure, the O—H group forms both an intra- and an intermolecular O—H⋯O hydrogen bond; the former generates an S(5) ring and the latter leads to inversion-generated R ₂ ²(10) loops. The dimers are further linked into ribbons propagating along the a axis by C—H⋯O interactions, and the packing is consolidated by weak C—H⋯π interactions.

Related literature

For background to benzoctamine, see: Wilhelm & Schmidt (1969 ▶); Karama et al. (2010a ▶). For further synthetic details, see: Karama et al. (2010b ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set descriptors of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₀H₁₈O₂
M _r = 290.34
Triclinic,
a = 7.60940 (1) Å
b = 9.16090 (1) Å
c = 11.1735 (2) Å
α = 84.202 (1)°
β = 85.707 (1)°
γ = 69.895 (1)°
V = 727.02 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.57 × 0.39 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.954, T _max = 0.978
14851 measured reflections
5283 independent reflections
4634 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.130
S = 1.06
5283 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033538/hb6360sup1.cif

e-67-o2487-sup1.cif^{(20.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033538/hb6360Isup2.hkl

e-67-o2487-Isup2.hkl^{(258.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033538/hb6360Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.948 (18)	2.08 (2)	2.600 (2)	113 (2)
O2—H1O2⋯O1ⁱ	0.948 (18)	2.01 (2)	2.8041 (10)	140 (2)
C14—H14A⋯O2ⁱⁱ	1.00	2.41	3.3909 (12)	166
C17—H17A⋯Cg1ⁱⁱⁱ	1.00	2.92	3.6542 (10)	131
C20—H20A⋯Cg1^iv	0.95	2.79	3.6357 (11)	149

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

Acknowledgments

UK, AIM and NA are grateful to the Deanship of Scientific Research, College of Science, King Saud University (KSU), for funding the synthetic chemistry work under Research Grant No. RGP-VPP-128.

supplementary crystallographic information

Comment

Benzoctamine is a clinically useful drug for the treatment of anxiety (Wilhelm & Schmidt, 1969) and our research group recently reported (Karama et al., 2010a) the synthesis of bishomobenzoctamine (Karama et al., 2010b) as it is a structural mimic of benzoctamine and was derived from anthrone which might be exhibited antidepressant activity. The title compound is the key intermediate for the synthesis of bishomobenzoctamine and its crystal structure is presented here.

In the molecular structure (Fig 1), the central 6-membered ring (C1/C6–C8/C13/C14) adopts a boat conformation with puckering amplitude Q = 0.6082 (9) Å, θ = 91.42 (8)° and φ = 120.69 (9)° (Cremer & Pople, 1975). The terminal benzene rings (C1–C6 and C8–C13) make a dihedral angle of 42.66 (4)° to each other. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

The crystal packing is shown in Fig. 2. The molecules are linked by the intermolecular O2—H1O2···O1 hydrogen bonds (Table 1) and generating R²₂(10) ring motifs (Bernstein et al., 1995). These ring motifs are further linked into ribbons along a axis via intermolecular C14—H14A···O2 hydrogen bonds (Table 1). In addition, the C—H···π interactions (Table 1) which involves C17 and C20 with the phenyl ring (Cg1; C1–C6) further stabilized the structure.

Experimental

To 12-Bromo-9-(prop-2-en-1-yl)-9,10-dihydro-9,10-ethanoanthracen-12-carbaldehyde (Karama et al., 2010a) (1 g, 2.85 mmol) in THF (10 ml) was added 1M aqueous NaOH (10 ml). The mixture was stirred at room temperature for 4 h, extracted with ether twice, washed with water, dried with MgSO₄ and the solvent was evaporated in vacuo to yield the crude product. The crude product was purified by column chromatography on silica gel (petroleum ether–ethyl acetate 5:1) and product was crystallized from EtOAc to reveal the title compound as colourless blocks.