2-Benzoyl-4-chloro­phenyl benzoate

Bushra Begum A; Mohammed Al-Ghorbani; Suresh Sharma; Vivek K Gupta; Shaukath Ara Khanum

doi:10.1107/S1600536813014396

. 2013 May 31;69(Pt 6):o999–o1000. doi: 10.1107/S1600536813014396

2-Benzoyl-4-chlorophenyl benzoate

Bushra Begum A ^a, Mohammed Al-Ghorbani ^a, Suresh Sharma ^b, Vivek K Gupta ^b, Shaukath Ara Khanum ^a,^*

PMCID: PMC3685129 PMID: 23795148

Abstract

In the title compound, C₂₀H₁₃ClO₃, the dihedral angles between the benzoate and the chlorobenzene and benzoyl rings are 68.82 (5) and 53.76 (6)°, respectively, while the dihedral angle between the benzoyl and benzoate rings is 81.17 (5)°. The eight atoms of the benzoyl residue are essentially planar with the exception of the O atom which lies 0.1860 (5) Å out of their mean plane (r.m.s. deviation = 0.97 Å). The nine atoms of benzoate residue are also essentially planar (r.m.s. deviation = 0.20 Å) with the ester O atom showing the greatest deviation [0.407 (12) Å] from their mean plane. In the crystal, molecules are connected into centrosymmetric dimers by pairs of C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Sieroń et al. (2004 ▶); Mahendra et al. (2005 ▶); Naveen et al. (2006 ▶). For the biological activity of the title compound, see: Belluti et al. (2011 ▶); Revesz et al. (2004 ▶); Khanum et al. (2004 ▶, 2009 ▶, 2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₀H₁₃ClO₃
M _r = 336.75
Triclinic,
a = 9.1934 (2) Å
b = 9.8641 (3) Å
c = 10.0778 (3) Å
α = 94.033 (2)°
β = 114.207 (2)°
γ = 102.512 (2)°
V = 800.64 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T _min = 0.871, T _max = 1.000
18813 measured reflections
3131 independent reflections
2631 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.084
S = 1.03
3131 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(23.7KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014396/go2090sup1.cif

e-69-0o999-sup1.cif^{(23.7KB, cif)}

Click here for additional data file.^{(150.5KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014396/go2090Isup2.hkl

e-69-0o999-Isup2.hkl^{(150.5KB, hkl)}

Click here for additional data file.^{(5.8KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813014396/go2090Isup3.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
C20—H20⋯O7ⁱ	0.93	2.50	3.394 (2)	162

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Symmetry code: (i) Inline graphic .

Acknowledgments

SAK gratefully acknowledges financial support provided by the UGC, New Delhi, under the Major Research Project Scheme.

supplementary crystallographic information

Comment

The benzophenone nucleus is an important part of the therapeutically interesting drug candidate as inhibitors of HIV-1 reverse transcriptase RT, cancer (Revesz et al., 2004) and inflammatory (Khanum et al., 2004; Khanum et al., 2009; Khanum et al., 2010). Therefore, a number of benzophenone analogues were synthesized, and their chemistry has been extensively studied. The benzophenone moiety, a structural element often seen in compounds from natural sources, presents a variety of biological activities such as anti-inflammatory, antimalarial and anticancer and demonstrated to be a versatile pharmacophoric nucleus, largely used in medicinal chemistry programs (Belluti et al., 2011). The importance of these substances is basically due to the diverse biological and chemical properties that they possess. In view of the above importance and to understand the conformation of the benzophenone moiety, the crystal structure determination of the title compound, was carried out. Bond lengths and bond angles of the title molecule show a fair amount of agreement with some related molecules related structures (Sieroń et al., 2004; Naveen et al., 2006; Mahendra et al., 2005). All bond lengths and angles are within expected values (Allen et al., 1987). The title compound has three benzene rings which are linked by carbonyl and ester groups. The dihedral angles between the ring (C1–C6) and (C8–C13) is 68.82 (5)°, ring (C1–C6) and (C16–C21) is 53.76 (6)° and ring (C8–C13) makes a dihedral angle of 81.17 (5)° with ring (C16–C21). The conformation of attachment of the benzoyl and benzoate rings to the central benzene ring can be characterized by torsion angles C6—C1—C7—C8 and C1—C2—O14—C15 of -54.9 (2) and -58.4 (2)°, respectively. The double bonds C7═O7 and C15═O15 are confirmed by their respective distances of 1.214 (2) and 1.196 (2) Å. Packing view of the molecules in the unit cell viewed down the a axis is shown in Fig. 2. The molecules are linked by intermolecular C20—H20···O7 interactions through hydrogen bonding of the carbonyl (benzophenone moiety) and ester substituent. The interaction with a neighbouring molecule is related to the other by a centre of inversion and form hydrogen-bonded dimer unit. Each unit is independently stacked when viewed down the a axis Fig.3.

Experimental

To a solution of (2-hydroxy-5-chlorophenyl) phenyl methanone (1, 1.99 g, 8.6 mmol) in 10% sodium hydroxide solution, benzoyl chloride (1.10 g, 8.6 mmol) was added with constant stirring. The reaction mixture was cooled to 0°C, made alkaline by adding 10% sodium solution and stirring was continued for about 1 h. The separated solid was extracted with ether (3 × 20 ml), the organic layer was washed with 10% sodium hydroxide solution (3 × 15 ml) and with distilled water (3 × 30 ml). The organic layer was dried over anhydrous sodium sulfate and ether was removed to afford crude product, which on recrystallization with alcohol gave white crystals of title compound. Yield: 71%, m.p. 365–367K.