Crystal structure of 2-(11-oxo-10H,11H-indeno­[1,2-b]chromen-10-yl)-2,3-di­hydro-1H-indene-1,3-dione

Joel T Mague; Shaaban K Mohamed; Mehmet Akkurt; Antanr A Abdelhamid; Mustafa R Albayati

doi:10.1107/S2056989015007495

. 2015 Apr 22;71(Pt 5):o333–o334. doi: 10.1107/S2056989015007495

Crystal structure of 2-(11-oxo-10H,11H-indeno[1,2-b]chromen-10-yl)-2,3-dihydro-1H-indene-1,3-dione

Joel T Mague ^a, Shaaban K Mohamed ^b,^c, Mehmet Akkurt ^d, Antanr A Abdelhamid ^e, Mustafa R Albayati ^f,^*

PMCID: PMC4420077 PMID: 25995934

Abstract

In the title molecule, C₂₅H₁₄O₄, the fused-ring system consisting of four rings is approximately planar, with a dihedral angle of 9.62 (5)° between the planes of the indene ring system and the benzene ring. The dihydroindene-1,3-dione unit makes a dihedral angle of 63.50 (2)° with the mean plane of the fused-ring system. A weak C—H⋯O interaction organizes the molecules into a helical chain along the b axis. In addition, there is a π–π stacking interaction between the five-membered rings of adjacent fused-ring systems, with a centroid–centroid distance of 3.666 (1) Å.

Keywords: crystal structure, indandiones, chromenes, coumarins, hydrogen bonding, π–π stacking

Related literature

For synthesis and biological properties of chromene scaffolds, see: RamaGanesh et al. (2010 ▸); O’Kenedy & Thornes (1997 ▸); Zabradnik (1992 ▸). For the bioactivity of fused chromenes, see: Bargagna et al. (1992 ▸); Ermili et al. (1979 ▸).

Experimental

Crystal data

C₂₅H₁₄O₄
M _r = 378.36
Monoclinic,
a = 8.7409 (2) Å
b = 14.4740 (3) Å
c = 14.2774 (3) Å
β = 101.141 (1)°
V = 1772.28 (7) Å³
Z = 4
Cu Kα radiation
μ = 0.78 mm⁻¹
T = 150 K
0.23 × 0.22 × 0.11 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T _min = 0.86, T _max = 0.92
28946 measured reflections
3495 independent reflections
3189 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.090
S = 1.06
3495 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXL2014.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015007495/is5397sup1.cif

e-71-0o333-sup1.cif^{(864.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007495/is5397Isup2.hkl

e-71-0o333-Isup2.hkl^{(191.9KB, hkl)}

Click here for additional data file.^{(7.1KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015007495/is5397Isup3.cml

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015007495/is5397fig1.tif

The molecular structure of the title compound with labeling scheme and 50% probability ellipsoids.

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015007495/is5397fig2.tif

A packing diagram of the title compound, showing a chain structure formed by C—H⋯O interactions (dashed lines).

CCDC reference: 1059989

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
C12H12O4ⁱ	0.95	2.54	3.4687(15)	166

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Symmetry code: (i) Inline graphic .

Acknowledgments

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

supplementary crystallographic information

S1. Comment

The synthesis of chromenes scaffolds has attracted considerable attention from organic and medicinal chemists for many years as larg number of natural products contain this heterocyclic nucleus (RamaGanesh et al., 2010). They are widely used as additives in food, perfumes, cosmetics, pharmaceuticals (O'Kenedy & Thornes, 1997), optical brighteners, dispersed fluorescent and laser dyes (Zabradnik, 1992). Fused chromene ring systems have platelet anti-aggregating, local anesthetic (Bargagna et al., 1992) and also exhibit antidepressant effects (Ermili et al., 1979). In this view and following to our study in synthesis of bio-active hetero-cyclic molecules, we report in this study the synthesis and crystal structure of the title compound.

In the title molecule (Fig. 1), there is a slight fold in the larger fused ring moiety along the C1···O1 line with a dihedral angle between the mean planes of C2–C10 and C11–C16 rings being 9.62 (5)°. The dihedral angle between the mean planes of C1–C16/O1 and C17–C25 ring systems is 63.50 (2)°. The molecules associate along the 2₁ axes via a weak C12—H12···O4ⁱ [symmetry code: (i) 1-x, -1/2+y, 1/2-z] hydrogen bond to form a helical chain (Table 1 and Fig. 2). In addition, there is a π–π stacking interaction between the five-membered C2–C4/C9/C10 ring and its centrosymmetrically related counterpart with a centroid-centroid distance of 3.666 (1) Å, an interplanar distance of 3.575 (1) Å and a centroid offset of 0.812 (1) Å.

S2. Experimental

In 30 ml of ethanol, a mixture of 1 mmol (122 mg) of salicylaldehyde and 2 mmol (292 mg) of 1H-indene-1,3(2H)-dione has been refluxed in the presence of a guanidine derivative as a lewise base catalyst. The reaction was monitored by TLC till completion after 5 h. On cooling, the solid product was collected by filteration, dried under vacuum and recrystallized from dimethylformamide (DMF). Single crystals suitable for X-ray diffraction were obtained by further crystallization from DMF. M.p. 513 K.