(4-Hydr­oxy-2,5-dimethyl­phen­yl)phenyl­methanone

Rodolfo Moreno-Fuquen; Leidy J Valencia; Alan R Kennedy; Denise Gilmour; R H De Almeida Santos

doi:10.1107/S1600536809039488

. 2009 Oct 3;65(Pt 11):o2614. doi: 10.1107/S1600536809039488

(4-Hydroxy-2,5-dimethylphenyl)phenylmethanone

Rodolfo Moreno-Fuquen ^a,^*, Leidy J Valencia ^a, Alan R Kennedy ^b, Denise Gilmour ^b, R H De Almeida Santos ^c

PMCID: PMC2971310 PMID: 21578230

Abstract

The title compound, C₁₅H₁₄O₂, was obtained by Friedel–Crafts acylation between 2,5-dimethylphenol and benzoyl chloride in the presence of aluminium chloride as a catalyst. The dihedral angle between the benzene rings is 61.95 (4)°. In the crystal, O—H⋯O hydrogen bonding and C—H⋯O weak interactions lead to polymeric C(6), C(8) and C(11) chains along the a, b and c-axis directions, respectively.

Related literature

For background information on the anti-fungal and anti-inflamatory biological activity of benzophenones, see: Naldoni et al. (2009 ▶); Selvi et al. (2003 ▶); Naveen et al. (2006 ▶). For 104 benzophenone molecules, see: Cox et al. (2008 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C₁₅H₁₄O₂
M _r = 226.26
Orthorhombic,
a = 12.1392 (10) Å
b = 8.1386 (7) Å
c = 23.665 (2) Å
V = 2338.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 123 K
0.25 × 0.12 × 0.05 mm

Data collection

Oxford Diffraction Gemini S diffractometer
Absorption correction: multi-scan (CrysAlis CCD; Oxford Diffraction, 2009 ▶) T _min = 0.904, T _max = 1.000
9067 measured reflections
2059 independent reflections
1061 reflections with I > 2σ(I)
R _int = 0.061

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.058
S = 0.73
2059 reflections
158 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PARST95 (Nardelli, 1995 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039488/hg2568sup1.cif

e-65-o2614-sup1.cif^{(17.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039488/hg2568Isup2.hkl

e-65-o2614-Isup2.hkl^{(101.2KB, hkl)}

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
O2—H2⋯O1ⁱ	0.84	1.92	2.6973 (15)	154
C15—H15B⋯O1ⁱⁱ	0.98	2.62	3.352 (2)	132
C4—H4⋯O2ⁱⁱⁱ	0.95	2.67	3.454 (2)	140

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

Acknowledgments

RMF is grateful to the Spanish Research Council (CSIC) for the use of a free-of-charge licence to the Cambridge Structural Database (Allen, 2002 ▶). RMF also thanks the Universidad del Valle, Colombia, and the Instituto de Química de São Carlos, Brazil, for partial financial support.

supplementary crystallographic information

Comment

The title compound, C₁₅H₁₄O₂, (4-Hydroxy-2,5-dimethyl-phenyl)-phenyl-methanone), (I), is part of a series of studies on benzophenone, which have been made in our research group. Benzophenone analogue systems show various anti-fungal and anti-inflamatory biological activities (Naldoni et al., 2009 and Selvi et al., 2003). The presence of various substituents in the benzophenone nucleus is essential to determining the quantitative structure-activity relationships of these systems. Some studies were carried out to show that methyl-substituted benzophenones exhibit anti-fungal properties (Naveen et al., 2006). In order to present the molecular conformation of (I), to analyse the type of hydrogen-bonds formed in (I) and to study its supramolecular behavior, the title compound was synthesized. The molecular structure of the title compound is shown in Fig. 1. The bond lengths and bond angles of (I) are in good agreement with the standard values and correspond to those observed in (4-Hydroxy-3-methylphenyl)(4- methylphenyl)methanone (Naveen et al., 2006). The two aromatic rings in the title structure form a dihedral angle of 61.95 (4)°. This value is greater than the value presented in the stable, orthorhombic form of unsubstituted benzophenone (54°) and follows the standard behavior of the majority of benzophenone molecules [104 benzophenone molecules, Cox et al., 2008]. The title molecule is characterized by the formation of O—H···O hydrogen-bonds and other C—H···O weak interactions (Table 1, Nardelli, 1995). The strongest hydrogen bond O—H···O interaction is responsible for crystal growth in [100] direction. Indeed, in a first substructure, atom O2 in the molecule at (x, y, z) acts as hydrogen bond donor to carbonyl O1 atom in the molecule at (x - 1/2, -y + 1/2, -z + 1). The propagation of this interaction forms a C(8) (Etter, 1990) chain running along [100] direction (Fig. 2). In a second substructure, atom C15 in the molecule at (x, y, z) links with weak interaction to carbonyl O1 atom in the molecule at (-x + 3/2, y - 1/2, z). The propagation of this interaction forms C(6) continuous chains via C15—H15B···O1 and running along [010] direction (Fig. 3). Finally in a third sub-structure, atom C4 in the molecule at (x, y, z) links with weak interaction to hydroxyl O2 atom in the molecule at (x, -y + 3/2, z - 1/2). The propagation of this interaction forms C(11) continuous chains and running along [001] direction. All of these interactions in [100], [010] and [001] directions define the bulk structure of the crystal.

Experimental

2,5-dimethylphenol (0.50 g, 4.10 mmol) was added to a solution of anhydrous aluminium chloride (0.40 g, 3.00 mmol) in dry dichloromethane (25 ml). The resulting solution was cooled and then a benzoyl chloride (0.80 g, 5.70 mmol) was slowly added at 0–5° C. After complete addition, the mixture was allowed to stir at room temperature for 0.5 h, and then it was heated up to 50° C for 1 h. The reaction mixture was poured onto ice (100 g) and conc. HCl (10 ml). The crude product was isolated by extraction with dichloromethane. The combined organic layers were washed with 10% aqueous NaOH, water, and then the solution was dried over Na₂SO₄ and it was evaporated at room temperature.