N-(2-Benzoyl-4-chloro­phen­yl)-4-chloro­benzene­sulfonamide

Arto Valkonen; Ryszard Gawinecki; Henryk Janota; Borys Ośmiałowski; Erkki Kolehmainen

doi:10.1107/S1600536808007435

. 2008 Mar 29;64(Pt 4):o737. doi: 10.1107/S1600536808007435

N-(2-Benzoyl-4-chlorophenyl)-4-chlorobenzenesulfonamide

Arto Valkonen ^a,^*, Ryszard Gawinecki ^b, Henryk Janota ^b, Borys Ośmiałowski ^b, Erkki Kolehmainen ^a

PMCID: PMC2961035 PMID: 21202127

Abstract

The title compound, C₁₉H₁₃Cl₂NO₃S, is an N-arylsulfonyl derivative of 2-amino-5-chlorobenzophenone. The compound is biologically active and shows potential to be utilized as an inhibitor of CCR2 and CCR9 receptor functions. In the crystal structure, there is an intramolecular N—H⋯O hydrogen bond between the amide and carbonyl groups. The benzoyl and 4-chlorophenyl groups form intramolecular and intermolecular face-to-face contacts, with a dihedral angle of 10.6 (1)° between their mean planes in both cases, and centroid–centroid separations of 4.00 (1) and 4.25 (1) Å for the intra- and intermolecular interactions, respectively.

Related literature

For related literature, see: Basak et al. (2008 ▶); Fleming et al. (2003 ▶); Kolehmainen et al. (2003 ▶); Sternbach et al. (1962 ▶).

Experimental

Crystal data

C₁₉H₁₃Cl₂NO₃S
M _r = 406.26
Monoclinic,
a = 8.2307 (1) Å
b = 18.5014 (3) Å
c = 12.1364 (2) Å
β = 105.211 (1)°
V = 1783.38 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 173 (2) K
0.25 × 0.25 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: none
13987 measured reflections
4401 independent reflections
3534 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.084
S = 1.05
4401 reflections
238 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: COLLECT (Bruker, 2004 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003 ▶) and Mercury (Macrae et al., 2006 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007435/bi2286sup1.cif

e-64-0o737-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007435/bi2286Isup2.hkl

e-64-0o737-Isup2.hkl^{(211.3KB, 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
N1—H1⋯O1	0.865 (15)	2.20 (2)	2.798 (2)	126.1 (18)

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supplementary crystallographic information

Comment

The title compound was originally prepared to study its molecular structure by spectroscopy (Kolehmainen et al., 2003). The compound has a sulfone group showing strong electron acceptor capability and two S=O double bonds with ineffective conjugation properties with other double bonds. The compound has also shown a potential to be utilized as inhibitor of CCR2 (Basak et al., 2008) and CCR9 (Fleming et al., 2003) receptor functions. This potent antagonist can possibly be utilized in pharmaceutical compositions for treatment of CCR2 and CCR9 related diseases.

In the crystal, there is an intramolecular N—H···O hydrogen bond between the amide and carbonyl groups (Fig. 1). The benzoyl and 4-chlorophenyl groups form intramolecular (Fig. 2) and intermolecular face-to-face contacts (Fig. 3), with a dihedral angle of 10.6 (1)° between their mean planes in both cases, and a centroid-centroid separation of 4.00 (1) and 4.25 (1)Å for the intra- and intermolecular interactions, respectively.

Experimental

The title compound was obtained by condensation of 2-amino-5-chlorobenzophenone and 4-chlorobenzenesulfonyl chloride according to a previously described method (Sternbach et al., 1962). The reaction product was purified by crystallization from ethanol. The spectroscopic characterization (NMR, IR) has previously been reported by us (Kolehmainen et al., 2003). The single-crystal suitable for X-ray determination was obtained by extremely slow evaporation of a CDCl₃ solution in a NMR tube.