4-Chloro-2-(2-chloro­benzoyl)phenol

A Bushra Begum; S Madan Kumar; B C Manjunath; Shaukath Ara Khanum; N K Lokanath

doi:10.1107/S1600536813025609

. 2013 Sep 21;69(Pt 10):o1568. doi: 10.1107/S1600536813025609

4-Chloro-2-(2-chlorobenzoyl)phenol

A Bushra Begum ^a, S Madan Kumar ^b, B C Manjunath ^b, Shaukath Ara Khanum ^a,^*, N K Lokanath ^b

PMCID: PMC3790428 PMID: 24098247

Abstract

In the title molecule, C₁₃H₈Cl₂O₂, the dihedral angle between the benzene rings is 74.53 (9)°. An intramolecular O—H⋯O hydrogen bond leading to a S(6) ring is observed. In the crystal, the molecules are connected into a three-dimensional network by C—H⋯O and π–π [inter-centroid distance = 3.6254 (10) Å] interactions.

Related literature

For the biological activity of benzophenone derivatives, see: Khanum et al. (2005 ▶, 2010 ▶). For a related structure, see: Devaiah et al. (2006 ▶).

Experimental

Crystal data

C₁₃H₈Cl₂O₂
M _r = 267.09
Orthorhombic,
a = 16.0231 (4) Å
b = 7.4216 (2) Å
c = 19.6843 (5) Å
V = 2340.80 (10) Å³
Z = 8
Cu Kα radiation
μ = 4.87 mm⁻¹
T = 295 K
0.20 × 0.19 × 0.18 mm

Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T _min = 0.442, T _max = 0.474
15868 measured reflections
1972 independent reflections
1712 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.105
S = 1.06
1972 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); 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., 2008 ▶); software used to prepare material for publication: Mercury.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813025609/tk5253sup1.cif

e-69-o1568-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813025609/tk5253Isup2.hkl

e-69-o1568-Isup2.hkl^{(97.1KB, hkl)}

Click here for additional data file.^{(4.1KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813025609/tk5253Isup3.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
O16—H16⋯O9	0.82	1.88	2.598 (2)	146
C13—H13⋯O9ⁱ	0.93	2.50	3.413 (3)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the IOE and the University of Mysore for providing the single crystal X-ray diffractometer facility.

supplementary crystallographic information

1. Comment

The on-going research in synthesizing benzophenone derivatives in our laboratory resulted in the title molecule. These derivatives used in the preparation of anti-inflammatory (Khanum et al., 2010) and anti-fungal (Khanum et al., 2005) compounds.

In the title molecule (Fig. 1), the dihedral angle between chlorobenzene (C1–C6) and chlorohydroxybenzene (C10–C15) rings is 74.53 (9)°. The molecule features an intramolecular O—H..O hydrogen bond forming a S(6) ring (Table 1). The bond lengths and bond angles are similar to those in the 5-chloro-2-hydroxyphenyl-4-chlorophenyl-methanone structure (Devaiah et al., 2006)

The molecules are connected by C13–H13···O9 hydrogen bonds forming chains along the a axis (Fig. 2 and Table 1). Additional C6—Cl7···π(Cg1), Table 1, and π(Cg2···π(Cg2) interactions, with inter-centroid distance 3.6254 (10) Å [x-1, -y, z-1], lead to a three-dimensional architecture, Fig. 2; where Cg1: C1–C6 and Cg2: C10–C15.

2. Experimental

A mixture of anhydrous aluminium chloride (1.74 g, 12.94 mmol) and include the name of the compound here (2.0 g, 8.62 mmol), was protected from moisture by a calcium chloride guard tube and heated over an oil bath at 80–90 °C for 45 min. At the end of this period the contents were cooled and decomposed by acidulated ice-cold water. The residual solid was crushed into a powder, dissolved in ether (40 ml) and extracted with 10% sodium hydroxide (3 x 30 ml). The basic aqueous solution was neutralized with 10% hydrochloric acid. The filtered solid was washed with distilled water (3 x 30 ml) and recrystallized from ethanol to afford yellow needles of the title compound. Yield 1.6 g (80%). M.Pt: 357–359 K. IR (Nujol): 1615 ν(C═O), 3525–3655 cm^-1ν(OH). ¹H NMR (CDCl₃): δ 6.9–7.5 (m, 7H, Ar—H), 9.2 (bs, 1H, OH). EI–MS: m/z 267 (M+, 81), 266 (100), 154.5 (57), 111.5 (50). Anal. Calcd. for C₁₃H₈Cl₂O₂ (267): C, 58.46; H, 3.02; Cl, 26.55. Found: C, 58.54; H, 3.25; Cl, 26.32%.