4-[(Hy­droxy)(4-methyl­phen­yl)methyl­idene]isochroman-1,3-dione

Akoun Abou; Abdoulaye Djandé; Adama Saba; Thierry Chiavassa; Rita Kakou-Yao

doi:10.1107/S1600536811050975

. 2011 Dec 3;68(Pt 1):o3. doi: 10.1107/S1600536811050975

4-[(Hydroxy)(4-methylphenyl)methylidene]isochroman-1,3-dione

Akoun Abou ^a,^*, Abdoulaye Djandé ^b, Adama Saba ^b, Thierry Chiavassa ^c, Rita Kakou-Yao ^a

PMCID: PMC3254283 PMID: 22259535

Abstract

In the title compound, C₁₇H₁₂O₄, the six-membered heterocyclic ring adopts a distorted screw-boat conformation. The molecular structure exhibits an S(6) ring motif, owing to an intramolecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯O contacts generate an infinite chain along the c axis. There are also π–π stacking interactions between neighbouring isochromanedione benzene rings, with a centroid–centroid distance of 3.755 (1) Å, and C—O⋯π interactions with an O⋯centroid distance of 3.964 (2) Å.

Related literature

For the biological activity of isochromanones, see: Bianchi et al., (2004 ▶); Buntin et al. (2008 ▶). For π–π stacking interactions, see: Janiak (2000 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₇H₁₂O₄
M _r = 280.27
Monoclinic,
a = 15.6767 (6) Å
b = 5.9655 (2) Å
c = 14.4589 (4) Å
β = 102.961 (1)°
V = 1317.74 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.40 × 0.34 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer
12419 measured reflections
3304 independent reflections
2684 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.150
S = 1.08
3304 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811050975/fj2488sup1.cif

e-68-000o3-sup1.cif^{(24.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050975/fj2488Isup2.hkl

e-68-000o3-Isup2.hkl^{(158.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811050975/fj2488Isup3.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
O4—H4⋯O3	0.82	1.75	2.485 (2)	148
C7—H7⋯O2ⁱ	0.93	2.57	3.299 (2)	136

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Laboratoire de Physique des Interactions Ioniques et Spectropôle, Université de Provence, and Université Paul Cézanne, Faculté des Sciences et Techniques de Saint Jérôme, Marseille, France, for the use of their diffractometer.

supplementary crystallographic information

Comment

The title molecule is related to the isochromanone derivatives that are generally known as regulators of plant growth (Bianchi et al., 2004). Depending on their chemical structure and concentration they can act either as inhibitors or stimulators in these processes. Some substituted isochromanones isolated from myxobacteria strains were introduced as anti-fungal agents (Buntin et al., 2008).

The structure of the title compound (I) (Fig. 1) consists of two essentially planar benzene rings with the maximum deviations from the best planes of 0.035 (1) Å for atom C6 (benzene ring C4—C9) and 0.008 (2) Å for atoms C12 and C15 (benzene ring C11—C16). An S(6) ring motifs (Bernstein et al., 1995), arising from the intramolecular hydrogen bond O—H···O, generates a planar pseudo six-membered ring (maximum deviation from planarity being ∓0.055 (2) Å for atoms C1 and C10) to result in a tricyclic ring (Fig. 1). The dihedral angles between two benzene rings is 58.99 (8)° and that between the pseudo six-membered ring and benzene rings are 13.75 (8) ° (ring C4—C9) and 53.96 (8)° (ring C11—C16). The heterocyclic ring O1/C1—C5 adopts a distorted screw-boat conformation as judged from the puckering parameters (Cremer & Pople, 1975): Q = 0.0974 (17) Å, θ = 69.6 (1)° and φ = 132.6 (1)°. Furthermore, intermolecular C—H···O hydrogen bonds (Table 1) link molecules into infinite chains along the [001] (Fig. 2).

The supramolecular aggregation is completed by the presence of C—O···π interactions (O3···Cg3[x,1/2 - y,-3/2 + z] = 3.964 (2) Å, C2—O3···Cg3 = 83.89 (12)°, where Cg3 is the centroid of the benzene ring C11—C16 and π–π stacking between two parallel isochromandione-benzene C4—C9 rings; in the latter, the centroid···centroid distance, (Cg2···Cg2(-x,2 - y,-z) of 3.755 (1) Å), is less than 3.8 Å, the maximum regarded as relevant for π–π interactions (Janiak, 2000) (Fig.3).

Experimental

To a solution of p-Toluoyl chloride (4.10^-2 mole) in dried tetrahydrofuran (150 ml), was added dried triethylamine (0.12 mole) and homophtalic anhydride (4.10^-2 mole) by small portions over 30 min. The mixture was then refluxed for 3 h and poured in 300 ml of chloroform. The solution was acidified with dilute hydrochloric acid until the pH was 2 - 3. The organic layer was extracted, washed with water, dried over MgSO4 and the solvent removed. The crude product was recrystallized from chloroform-hexane (1/1, v/v) mixture. Yellow crystals of the title compound were obtained in a good yield: 85%; M.pt. 387–388 K.