Methyl 2-(N-methoxy­carbonyl­meth­yl-N-methylsulfamo­yl)benzoate

Naeem Ahmad; M Nawaz Tahir; Durre Shahwar; Muhammad Akmal Khan; Uzma Sana

doi:10.1107/S1600536809003742

. 2009 Feb 4;65(Pt 3):o449. doi: 10.1107/S1600536809003742

Methyl 2-(N-methoxycarbonylmethyl-N-methylsulfamoyl)benzoate

Naeem Ahmad ^a, M Nawaz Tahir ^b,^*, Durre Shahwar ^a, Muhammad Akmal Khan ^a, Uzma Sana ^a

PMCID: PMC2968464 PMID: 21582122

Abstract

In the title compound, C₁₂H₁₅NO₆S, the aromatic ring is oriented at dihedral angles of 64.76 (11) and 56.42 (13)° with respect to the planar methyl ester unit and the SO₂ group, respectively. The dihedral angle between the SO₂ group and the planar methoxycarbonylmethyl group is 50.42 (14)°. Intramolecular C—H⋯O hydrogen bonding results in the formation of an eight-membered ring. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules.

Related literature

For general background, see: Hanson et al. (1999 ▶). For related structures, see: Arshad et al. (2008 ▶); Shafiq et al. (2008a ▶,b ▶); Ma et al., 2003 ▶).

Experimental

Crystal data

C₁₂H₁₅NO₆S
M _r = 301.31
Orthorhombic,
a = 8.5830 (3) Å
b = 9.0966 (3) Å
c = 18.3329 (7) Å
V = 1431.36 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 (2) K
0.22 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.942, T _max = 0.965
16627 measured reflections
3558 independent reflections
2513 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.098
S = 1.01
3558 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ▶), 1509 Friedel pairs
Flack parameter: 0.12 (8)

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/S1600536809003742/hk2618sup1.cif

e-65-0o449-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003742/hk2618Isup2.hkl

e-65-0o449-Isup2.hkl^{(171KB, 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
C9—H9A⋯O1	0.97	2.20	3.125 (3)	159
C9—H9B⋯O1ⁱ	0.97	2.56	3.321 (3)	135
C12—H12B⋯O4ⁱⁱ	0.96	2.44	3.041 (4)	120

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

Acknowledgments

NA gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing his Scholarship under the Indigenous PhD Program (PIN 042–120599-PS2–156).

supplementary crystallographic information

Comment

Sulfonamides are a class of compounds, which find wide applications in medicinal chemistry (Hanson et al., 1999). Cyclic sulfonamides (benzothiazine) have biological activities such as lipoxygenase inhibition, and they are used as drugs for heart diseases. We are engaged in the syntheses of various derivatives of benzothiazine molecule (Arshad et al., 2008; Shafiq et al., 20082008a,b). We report herein the crystal structure of the title compound, (I), which is used as an intermediate for further syntheses.

In the molecule of the title compound, (I), (Fig. 1), the coordination around the S atom is a distorted tetrahedral. The crystal structure of methyl 2-(4-methoxypyrimidin-2-ylcarbamoylsulfamoyl)benzoate, (II) (Ma et al., 2003) has been reported, which also has a sulfamoylbenzoate moiety. In (I), the benzene ring A (C1-C6) is oriented with respect to the planar methyl ester moiety (O1/O2/C7/C8) and SO₂ group at dihedral angles of 64.76 (11)° and 56.42 (13)°, respectively. The dihedral angle between SO₂ moiety and the planar methoxycarbonylmethyl group (O5/O6/N1/C9/C10/C12) is 50.42 (14)°. Intramolecular C—H···O hydrogen bonding (Table 1) results in the formation of an eight-membered ring (S1/O1/N1/C1/C6/C7/C9/H9A).

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, sodium saccharine (20.5 g, 0.1 mol) and methylchloroacetic acid (10.85 g, 0.1 mol) were dissolved in DMF (50 ml) and refluxed for 1 h, and then ice was added for precipitation. The precipitate (12.8 g, 0.05 mol) was dissolved in methanol (50 ml), and sodium methoxide (5.4 g, 0.1 mol) was added, and then refluxed for 3 h. The volume was reduced to half by evaporation. Then, HCl was added on cooling and left overnight in refrigerator, which was then recrystallized from absolute ethanol.