(2E)-2-[(2H-1,3-Benzodioxol-5-yl)methyl­idene]-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/S1600536812009464

. 2012 Mar 10;68(Pt 4):o1015. doi: 10.1107/S1600536812009464

(2E)-2-[(2H-1,3-Benzodioxol-5-yl)methylidene]-2,3-dihydro-1H-inden-1-one

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

PMCID: PMC3343980 PMID: 22589889

Abstract

In the title compound, C₁₇H₁₂O₃, each of the five-membered rings in the inden-1-one and 1,3-benzodioxole residues is almost planar (r.m.s. deviations = 0.041 and 0.033 Å, respectively). A small twist about the single bond linking the two residues is evident [the C—C—C—C torsion angle = 8.7 (4)°]. Supramolecular zigzag layers propagating in the ac plane are formed in the crystal via C—H⋯O interactions. The layers are linked via π–π interactions between the five- and six-membered rings of 1,3-benzodioxole residues [centroid–centroid distance = 3.4977 (14) Å].

Related literature

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

Experimental

Crystal data

C₁₇H₁₂O₃
M _r = 264.27
Orthorhombic,
a = 12.6102 (12) Å
b = 7.3497 (10) Å
c = 26.569 (4) Å
V = 2462.5 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.35 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.967, T _max = 0.995
6424 measured reflections
2820 independent reflections
1697 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.136
S = 0.98
2820 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 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/S1600536812009464/hb6667sup1.cif

e-68-o1015-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009464/hb6667Isup2.hkl

e-68-o1015-Isup2.hkl^{(138.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812009464/hb6667Isup3.cml

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.95	2.47	3.290 (3)	144
C17—H17A⋯O1ⁱⁱ	0.99	2.46	3.302 (3)	143

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

Acknowledgments

The authors are grateful to the Center of Excellence for Advanced Materials Research and the Chemistry Department at King Abdulaziz University for providing 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 crystal and molecular structure of the title compound, 2-benzo[1,3]dioxol-5-ylmethylene-indan-1-one (I), has been determined in connection with recent structural studies on related derivatives (Asiri et al., 2012a; Asiri et al., 2012b). The motivation for the original synthesis was its relationship to biologically active compounds (Vera-DiVaio et al., 2009).

In the molecule of (I), Fig. 1, both five-membered rings are essentially planar. In the inden-1-one residue the r.m.s. deviation for the five atoms = 0.041 Å [maximum deviations = 0.033 (2) for the C8 atom and -0.033 (2) for the C7 atom] and in the 1,3-benzodioxole residue, the r.m.s. deviation = 0.033 Å [maximum deviations = 0.028 (3) [C17] and -0.028 (1) [O3]]. A twist in the molecule about the C10—C11 bond is evident with the C9—C10—C11—C16 torsion angle being 8.7 (4)°. The configuration about the C9═C10 bond [1.340 (3) Å] is E.

In the crystal packing, C—H···O interactions, Table 1, involving the bifurcated carbonyl-O atom link molecules into zigzag layers in the ac plane, Fig. 2. Layers are linked along the b axis viaπ–π interactions between the five- and six-membered rings of 1,3-benzodioxole residues [ring centroid···centroid distance = 3.4977 (14) Å, angle of inclination = 10.97 (12)° for symmetry operation 3/2 - x, -1/2 + y, z], Fig. 3.

Experimental

A solution of the piperonaldehyde (1.5 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 as light-yellow prisms. Yield: 93%; M. pt: 450–451 K.