Methyl 2-bromo-3-(4-chloro­benzene­sulfonamido)­benzoate

Ahmad Z Ghafoor; Brian Chang; Christopher L King; Ray J Butcher; Amol A Kulkarni

doi:10.1107/S1600536812048581

. 2013 Jan 31;69(Pt 2):o311. doi: 10.1107/S1600536812048581

Methyl 2-bromo-3-(4-chlorobenzenesulfonamido)benzoate

Ahmad Z Ghafoor ^a, Brian Chang ^a, Christopher L King ^b, Ray J Butcher ^b, Amol A Kulkarni ^a,^*

PMCID: PMC3569830 PMID: 23424576

Abstract

In the crystal structure of the title compound, C₁₄H₁₁BrClNO₄S, the molecules form inversion dimers with R ₂ ²(8) motifs through pairs of N—H⋯O hydrogen bonds. The benzene rings are not coplanar and subtend a dihedral angle of 66.27 (8)°. The carbomethoxy group makes a dihedral angle of 75.1 (1)° with the ring to which it is attached.

Related literature

Depending on their substitution patterns, sulfonamides display a wide array of biological activity. For their use as antimitotic, antibacterial and anti-obesity agents, see: Hu et al. (2008 ▶); Wydysh et al. (2009 ▶). For structures related to the development of novel antimicrobial agents, see: Kulkarni et al. (2012a ▶,b ▶). graphic file with name e-69-0o311-scheme1.jpg

Experimental

Crystal data

C₁₄H₁₁BrClNO₄S
M _r = 404.66
Monoclinic,
a = 7.9206 (2) Å
b = 9.4600 (3) Å
c = 20.0915 (6) Å
β = 94.505 (3)°
V = 1500.79 (8) Å³
Z = 4
Cu Kα radiation
μ = 6.84 mm⁻¹
T = 123 K
1.06 × 0.88 × 0.52 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2010 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T _min = 0.049, T _max = 0.198
5248 measured reflections
3012 independent reflections
2873 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.093
S = 1.08
3012 reflections
205 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Click here for additional data file.^{(18.7KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048581/ds2221sup1.cif

e-69-0o311-sup1.cif^{(18.7KB, cif)}

Click here for additional data file.^{(147.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048581/ds2221Isup2.hkl

e-69-0o311-Isup2.hkl^{(147.8KB, hkl)}

Click here for additional data file.^{(5.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812048581/ds2221Isup3.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
N1—H1A⋯O1ⁱ	0.80 (4)	2.22 (4)	2.978 (3)	158 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

AAK wishes to acknowledge Dr A. K. Wutoh, Dean of the College of Pharmacy, for the purchase of chemicals and solvents, as well as RCMI, Howard University, and CDRD, College of Pharmacy, Howard University, for their support. RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

supplementary crystallographic information

Comment

Depending on their substitution patterns, sulfonamides display a wide array of biological activity. These compounds have been used as antimitotic, antibacterial, anti-obesity agents. See: Hu et al. (2008); Wydysh et al. (2009). The crystal structure of the title compound has not previously been reported. The title compound was synthesized as an intermediate during our synthetic studies directed towards the development of novel antimicrobial agents (Kulkarni et al., 2012a, 2012b).

In the title compound (C₁₄H₁₁Br₁Cl₁N₁O₄S₁), the molecules form dimers through N—H···O hydrogen bonding to form R²₂(8) motifs. The two phenyl rings are not coplanar and have a dihedral angle of 66.27 (8)°. The carbomethoxy group makes a dihedral angle of 75.1 (1)° with the ring to which it is attached.

Experimental

A 25 ml one-neck flask equipped with a magnetic stir bar was charged with a solution of the methyl ester (230 mg, 1.0 mmole) in CH₂Cl₂ (4.0 ml). Pyridine (604 ml, 7.5 mmole) was added. The reaction mixture was cooled at 0 °C using ice-bath for 15 minutes. 4-chlorophenylsulfonyl chloride (253 mg, 1.2 mmole) was added to the reaction mixture. The reaction mixture was slowly warmed to RT and was stirred at RT for 4 h. The crude reaction mixture was poured into a separatory funnel containing 1 N HCl (20 ml) and CH₂Cl₂ (20 ml). The layers were separated, the organic layer was washed with water (2X 20 ml) and brine (1X 20 ml). It was dried over anhydr. Na₂SO₄. The solvent was evaporated in vacuo. The orange/brown oil thus obtained was purified using silica gel flash column chromatography. Elution with 40% EA in hexanes afforded the desired sulfonamide product as pale yellow crystals. mp 121–124 °C; ¹H-NMR (CDCl₃) d 7.80 (dd, J = 8.0, 2.0 Hz, 1H), 7. 68 (dt, J = 8.0, 2.0 Hz, 1H), 7.51 (dd, J = 8.0, 2.0 Hz, 1H), 7.41–7.31 (m, 4H), 3.86 (s, 3H). ¹³C-NMR (CDCl₃) d 165.9, 139.9, 137.1, 135.5, 133.4, 129.4, 128.6, 128.0, 127.7, 125.4, 115.1, 52.6.