4-[(4-Chloro­phen­yl)(hy­droxy)methyl­idene]isochromane-1,3-dione

Akoun Abou; Abdoulaye Djandé; Bintou Sessouma; Adama Saba; Rita Kakou-Yao

doi:10.1107/S160053681104829X

. 2011 Nov 19;67(Pt 12):o3349. doi: 10.1107/S160053681104829X

4-[(4-Chlorophenyl)(hydroxy)methylidene]isochromane-1,3-dione

Akoun Abou ^a,^*, Abdoulaye Djandé ^b, Bintou Sessouma ^b, Adama Saba ^b, Rita Kakou-Yao ^a

PMCID: PMC3238994 PMID: 22199843

Abstract

In the title compound, C₁₆H₉ClO₄, the six-membered heterocyclic ring adopts a screw-boat conformation. The benzene rings are oriented to each other at a dihedral angle of 59.26 (9)°. The molecular structure exhibits a ring motif, viz. S(6), owing to an intramolecular O—H⋯O hydrogen bond. The presence of C—H⋯O contacts generates an infinite chain along [001]. Also present are π–π stacking interactions between neighbouring isochromanedione benzene rings [centroid–centroid distance = 3.746 (1) Å], and C—O⋯π interactions [O⋯centroid = 3.934 (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 puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₆H₉ClO₄
M _r = 300.68
Monoclinic,
a = 15.4973 (4) Å
b = 5.9631 (1) Å
c = 14.4526 (3) Å
β = 102.661 (1)°
V = 1303.12 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
12213 measured reflections
3248 independent reflections
2693 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.163
S = 1.08
3248 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); 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/S160053681104829X/tk5016sup1.cif

e-67-o3349-sup1.cif^{(23.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104829X/tk5016Isup2.hkl

e-67-o3349-Isup2.hkl^{(156.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681104829X/tk5016Isup3.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
O14—H14⋯O12	0.82	1.76	2.492 (2)	148
C3—H3⋯O11ⁱ	0.93	2.56	3.288 (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 facilities.

supplementary crystallographic information

Comment

The title molecule is related to 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 of 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 planar benzene rings with the maximum deviations from the best planes of 0.035 (2) Å for atom C1 (benzene ring C1—C6) and ±0.007 (2) Å for atoms C15 and C16 (benzene ring C15—C20). An S(6) ring motif (Bernstein et al., 1995), arises from an intramolecular O—H···O hydrogen bond to generate a planar pseudo six-membered ring (maximum deviation from planarity being 0.059 (2) Å for atom C13) to result in a tricyclic ring system (Fig. 1). The dihedral angles between two benzene rings is 59.26 (9) and that between the pseudo six-membered ring and benzene ring C1—C6 is 13.65 (9) °. The heterocyclic ring C1/C6/C7/O8/C9/C10 adopts a screw-boat conformation as judged from the puckering parameters (Cremer & Pople, 1975): Q = 0.0952 (19) Å, θ = 67.5 (11)° and φ = 228.4 (12)°. Furthermore, intermolecular C—H···O contacts (Table 1) link molecules into infinite chains through along [001] (Fig. 2).

The supramolecular aggregation is completed by the presence of C—O···π interactions (O12···Cg3[x,1/2 - y,-1/2 + z] = 3.934 (2) Å, C9—O12···Cg3 = 83.48 (12)°, where Cg3 is the centroid of the benzene ring C15—C20, and π–π stacking between two parallel isochromanedione-benzene C1—C6 rings; in the latter, the centroid···centroid distance, (Cg2···Cg2 (-x,-y,-z) of 3.746 (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 4-chlorobenzoyl chloride (4.10 ^-2 mol) in dry tetrahydrofuran (150 ml ), was added dried triethylamine (0.12 mol) and homophthalic anhydride (4.10 ^-2 mol) in 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 a chloroform-hexane (1/1, v/v) mixture. Yellow crystals were obtained in a good yield: 90%; M.pt. 432–433 K.