(2E)-2-(Furan-2-yl­methyl­idene)-2,3-dihydro-1H-inden-1-one

Abdullah M Asiri; Hassan M Faidallah; Khulud F Al-Nemari; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812010501

. 2012 Mar 14;68(Pt 4):o1065. doi: 10.1107/S1600536812010501

(2E)-2-(Furan-2-ylmethylidene)-2,3-dihydro-1H-inden-1-one

Abdullah M Asiri ^a,^b,^‡, Hassan M Faidallah ^a, Khulud F Al-Nemari ^a, Seik Weng Ng ^c,^a, Edward R T Tiekink ^c,^*

PMCID: PMC3344023 PMID: 22589932

Abstract

In the title compound, C₁₄H₁₀O₂, the five-membered ring of the inden-1-one residue is almost planar (r.m.s. deviation = 0.035 Å). A twist about the single bond linking the two residues is evident [C—C—C—C torsion angle = −13.2 (5)°]. The three-dimensional architecture is stabilized by C—H⋯O (involving the trifurcated carbonyl O atom), C—H⋯π and π–π interactions [between the five- and six-membered rings of inden-1-one residues; ring centroid–centroid distance = 3.7983 (17) Å]. The sample studied was a non-merohedral twin; the minor component refined to approximately 36%.

Related literature

For the biological activity of related species, see: Vera-DiVaio et al. (2009 ▶). For related structures, see: Asiri et al. (2012a ▶,b ▶). For the treatment of twinned data, see: Spek (2009 ▶).

Experimental

Crystal data

C₁₄H₁₀O₂
M _r = 210.22
Monoclinic,
a = 5.9333 (8) Å
b = 7.6605 (6) Å
c = 22.386 (3) Å
β = 91.582 (14)°
V = 1017.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.25 × 0.25 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.978, T _max = 0.995
5052 measured reflections
3274 independent reflections
2683 reflections with I > 2σ(I)
R _int = 0.086

Refinement

R[F ² > 2σ(F ²)] = 0.081
wR(F ²) = 0.251
S = 1.10
3274 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.38 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010501/bt5838sup1.cif

e-68-o1065-sup1.cif^{(15.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010501/bt5838Isup2.hkl

e-68-o1065-Isup2.hkl^{(160.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010501/bt5838Isup3.cml

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

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

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.95	2.56	3.414 (4)	149
C8—H8A⋯O1ⁱⁱ	0.99	2.37	3.343 (4)	166
C14—H14⋯O1ⁱⁱⁱ	0.95	2.45	3.372 (4)	164
C8—H8B⋯Cg1^iv	0.99	2.70	3.517 (3)	140

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

Acknowledgments

The authors are grateful to the Center of Excellence for Advanced Materials Research and the Chemistry Department at King Abdulaziz University for providing the research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

The title compound, 2-furan-2-ylmethylene-indan-1-one (I), has been investigated crystallographically in connection with recent structural studies on related derivatives (Asiri et al., 2012a; Asiri et al., 2012b). The motivation for the original synthesis of (I) is its relationship to biologically active compounds (Vera-DiVaio et al., 2009).

In the molecule of (I), Fig. 1, the five-membered ring of the inden-1-one residue is planar with the r.m.s. deviation for the five atoms = 0.035 Å [maximum deviations = 0.031 (2) for the C9 atom and -0.026 (3) for the C8 atom]. A twist in the molecule about the C10—C11 bond is evident with the C9—C10—C11—C12 torsion angle being -13.2 (5)°. The configuration about the C9═C10 bond [1.346 (4) Å] is E.

The carbonyl-O1 atom is tri-furcated, forming three C—H···O interactions which lead to a three-dimensional architecture. Additional interactions in the crystal packing include C—H···π interactions, Table 1, as well as π–π contacts between the five- and six-membered rings of inden-1-one residue [ring centroid···centroid distance = 3.7983 (17) Å, angle of inclination = 1.02 (14)° for symmetry operation 1 - x, -y, 1 - z], Fig. 2.

Experimental

A solution of the furan-2-carboxaldehyde (0.95 g, 0.01 M) in ethanol (20 ml) was added to a stirred solution of 1-indanone (1.3 g,0.01 M) in (20%) ethanolic KOH (20 ml), and stirring was maintained at room temperature for 6 h. The reaction mixture was then poured into water (200 ml) and set aside overnight. The precipitated solid product was collected by filtration, washed with water, dried and recrystallized from ethanol. Yield: 92%. M.pt: 393–395 K.