Methyl (4-bromo­benzene­sulfonamido)acetate

Muhammad Nadeem Arshad; M Nawaz Tahir; Islam Ullah Khan; Ejaz Ahmad; Muhammad Shafiq

doi:10.1107/S1600536808037550

. 2008 Nov 20;64(Pt 12):o2380. doi: 10.1107/S1600536808037550

Methyl (4-bromobenzenesulfonamido)acetate

Muhammad Nadeem Arshad ^a, M Nawaz Tahir ^b,^*, Islam Ullah Khan ^a, Ejaz Ahmad ^a, Muhammad Shafiq ^a

PMCID: PMC2960029 PMID: 21581352

Abstract

The title compound, C₉H₁₀BrNO₄S, is an intermediate for the formation of benzothiazines. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules, forming R ₂ ²(10) ring motifs, which are linked into a two-dimensional polymeric sheet through intermolecular C—H⋯O hydrogen bonds.

Related literature

For general background, see: Arshad et al. (2008 ▶); Tahir et al. (2008 ▶). For a related structure, see: Bornaghi et al. (2005 ▶). For ring motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₉H₁₀BrNO₄S
M _r = 308.15
Triclinic,
a = 6.0451 (2) Å
b = 7.0369 (2) Å
c = 13.8695 (5) Å
α = 83.866 (2)°
β = 81.190 (1)°
γ = 87.027 (2)°
V = 579.31 (3) Å³
Z = 2
Mo Kα radiation
μ = 3.73 mm⁻¹
T = 296 (2) K
0.23 × 0.18 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.449, T _max = 0.639
13148 measured reflections
2846 independent reflections
1893 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.116
S = 1.04
2846 reflections
145 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037550/hk2573sup1.cif

e-64-o2380-sup1.cif^{(16KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037550/hk2573Isup2.hkl

e-64-o2380-Isup2.hkl^{(136.8KB, 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⋯O2ⁱ	0.86	2.41	2.987 (4)	125
C3—H3A⋯O3ⁱⁱ	0.97	2.50	3.410 (4)	156

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

MNA gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a Scholarship under the Indigenous PhD Programme (PIN 042-120607-PS2-183).

supplementary crystallographic information

Comment

The glycine methyl ester is the simplest among the amino acids and the p-bromobenzenesulfonyl chloride is also comercially available. We have synthesized the title compound, (I), from their condensation. It has been prepared as an intermediate for the formation of benzothiazines, which are of our research interest (Arshad et al., 2008; Tahir et al., 2008).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths (Allen et al., 1987) and angles are within normal ranges, and are comparable with the corresponding values in N-(2-nitrophenylsulfonyl)glycine methyl ester, (II), (Bornaghi et al., 2005). Ring A (C4-C9) is, of course, planar, and the Br atom lies slightly out of the ring plane [0.069 (3) Å]. The S1-N1 bond is almost perpendicular to the ring plane, with N1-S1-C4-C5 [-83.4 (3)°] and/or N1/S1/C4/C9 [93.7 (3)°] torsion angles. The (O1/O2/C1-C3) moiety is planar, and it is oriented with respect to ring A at a dihedral angle of 87.74 (3)°.

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 1) link the molecules to form R₂²(10) ring motifs (Bernstein et al., 1995), in which they are linked to form a two dimensional polymeric sheet through intermolecular C-H···O hydrogen bonds (Table 1, Fig. 2).

Experimental

Glycine methyl ester hydrochloride (0.246 g, 1.95 mmol) was dissolved in water (10 ml) in round bottom flask. The pH of the solution was adjusted to 8–9 using sodium carbonate (1 N), and then 4-bromo benzene sulfonyl chloride (0.5 g, 1.95 mmol) was added. The mixture was stirred for 2 h at room temperature. During the reaction, pH was strictly maintained at 8–9 as HCl produced, which lowers the pH. Colorless solid product obtained was washed, dried and recrystalized from methanol for X-ray analysis (m.p. 393-394 K).