(4-Fluoro­phen­yl)(4-hy­droxy-3-methyl­phen­yl)methanone

C S Dileep; V Lakshmi Ranganatha; N K Lokanath; S A Khanum; M A Sridhar

doi:10.1107/S1600536813033783

. 2013 Dec 21;70(Pt 1):o76. doi: 10.1107/S1600536813033783

(4-Fluorophenyl)(4-hydroxy-3-methylphenyl)methanone

C S Dileep ^a, V Lakshmi Ranganatha ^b, N K Lokanath ^a, S A Khanum ^b, M A Sridhar ^a,^*

PMCID: PMC3914103 PMID: 24527008

Abstract

In the title compound, C₁₄H₁₁FO₂, the two benzene rings are not coplanar, with a dihedral angle of 57.45 (12)° between their planes. In the crystal, molecules are linked by an O—H⋯O hydrogen bond, forming a 2₁ helical chain along the b axis.

Related literature

For the biological activities of benzophenone derivatives, see: Khanum et al. (2004 ▶); Naveen et al. (2006 ▶); Selvi et al. (2003 ▶). For related structures, see: Mahendra et al. (2005 ▶); Dileep, Lakshmi Ranganatha et al. (2013 ▶); Dileep, Prashanth et al. (2013 ▶). For bond-length data, see: Allen et al. (1987 ▶). graphic file with name e-70-00o76-scheme1.jpg

Experimental

Crystal data

C₁₄H₁₁FO₂
M _r = 230.23
Monoclinic,
a = 5.9265 (10) Å
b = 13.112 (2) Å
c = 14.556 (2) Å
β = 96.875 (7)°
V = 1123.0 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.85 mm⁻¹
T = 296 K
0.27 × 0.25 × 0.23 mm

Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.804, T _max = 0.829
7047 measured reflections
1769 independent reflections
1317 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.273
S = 1.16
1769 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033783/is5325sup1.cif

e-70-00o76-sup1.cif^{(22.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033783/is5325Isup2.hkl

e-70-00o76-Isup2.hkl^{(87.2KB, hkl)}

Click here for additional data file.^{(4.5KB, cml)}

Supporting information file. DOI: 10.1107/S1600536813033783/is5325Isup3.cml

Additional supporting information: 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⋯O9ⁱ	0.82	1.91	2.688 (3)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would like to thank the University of Mysore for providing the diffractometer facility under IoE. CSD would like to thank the University of Mysore for awarding an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009–2010/10.07.2012. VLR acknowledges the financial support provided by the Department of Science and Technology, New Delhi, under the INSPIRE–Fellowship scheme [IF110555]. SAK gratefully acknowledges the financial assistance provided by UGC under major research project scheme [F.39/737/2010 (SR)].

supplementary crystallographic information

1. Comment

The great interest in the benzophenone substances is fundamentally due to their diverse biological and chemical properties. Benzophenone and related compounds have a wide variety of biological activities such as anti-fungal and anti-inflammatory activities (Khanum et al., 2004; Selvi et al., 2003). The presence of various substituents in the benzophenone nucleus is essential in determining the quantitative structure-activity relationships of these systems. The competence of benzophenones as chemotherapeutic agents, especially as inhibitors of HIV-1 reverse transcriptase RT, cancer and inflammation, is well established. Their chemistry has been studied extensively. In addition, methyl-substituted benzophenones exhibit chemotherapeutical activity against fungi. Some studies were carried out to show that methyl-substituted benzophenones exhibit anti-fungal properties (Naveen et al., 2006). In view of its extensive background, the title compound was prepared and characterized by single-crystal X-ray diffraction.

In the molecular structure of the title compound (Fig. 1), bond lengths and angles do not show large deviations and are comparable with those reported for a similar structure (Mahendra et al., 2005; Dileep, Lakshmi Ranganatha et al., 2013; Dileep, Prashanth et al., 2013). The mean plane angle between the two phenyl rings (C2–C7) and (C10–C13/C15/C17) is 57.45 (12)°. The bond length between C2 and F1 is 1.357 (4) Å and is normal with the standard value (Allen et al., 1987). The conformation of the attachment of the two phenyl rings to the central carbonyl group can also be characterized by torsion angles (O9—C8—C5—C6) and (O9—C8—C10—C17) of -141.1 (3) and -152.8 (3)°, respectively. The crystal structure is stabilized by intermolecular O—H···O hydrogen bonds. The molecular packing when viewed down the a axis is shown in Fig. 2.

2. Experimental

The title compound was synthesized by a mixture of anhydrous aluminium chloride (0.03 mol) and 2-methyl-phenyl-4-fluorobenzoate (0.02 mol) in dry nitrobenzene (40 ml) was protected from moisture by calcium chloride guard tube and refluxed at 80–900 °C with stirring for 45 min. At the end of this period the solution was cooled and decomposed by acidulated ice-cold water. Nitrobenzene was removed by steam distillation. The residual solid was crushed into powder, dissolved in ether and extracted with 10 percent sodium hydroxide. The basic aqueous solution was neutralized with 10 percent hydrochloric acid. The filtered solid was washed with distilled water and recrystallized from ethanol to afford pale yellow needles of (4-fluorophenyl)(4-hydroxy-3-methylphenyl)methanone.