Methyl 2-(benzene-sulfonamido)acetate.

The title compound, C(9)H(11)NO(4)S, is of inter-est as a precursor to biologically active benzothia-zines. The crystal structure is stabilized by inter-molecular N-H⋯O and C-H⋯O inter-actions.

Related literature

For the synthesis and biological evaluation of sulfur-containing heterocyclic compounds, see: Zia-ur-Rehman et al. (2005 ▶, 2006 ▶, 2009 ▶); Xiao & Timberlake (2000 ▶); Martinez et al. (2000 ▶); Berredjem et al. (2000 ▶); Lee & Lee (2002 ▶). For related literature on sulfonamides, see: Esteve & Bidal (2002 ▶); Soledade et al. (2006 ▶). For related structures, see: Gowda et al. (2007a ▶,b ▶,c ▶).

Experimental

Crystal data

C9H11NO4S

M = 229.26

Monoclinic,

a = 9.7268 (8) Å

b = 5.0781 (4) Å

c = 10.9286 (9) Å

β = 100.087 (3)°

V = 531.46 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.30 mm−1

T = 296 K

0.23 × 0.11 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.935, T max = 0.977

6159 measured reflections

2216 independent reflections

1944 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.092

S = 1.07

2216 reflections

137 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 394 Friedel pairs

Flack parameter: 0.089 (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: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680901616X/bt2940sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901616X/bt2940Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H11NO4S	F(000) = 240
Mr = 229.26	Dx = 1.433 Mg m−3
Monoclinic, P21	Melting point: 332 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 9.7268 (8) Å	Cell parameters from 2710 reflections
b = 5.0781 (4) Å	θ = 2.6–26.6°
c = 10.9286 (9) Å	µ = 0.30 mm−1
β = 100.087 (3)°	T = 296 K
V = 531.46 (7) Å3	Plates, colourless
Z = 2	0.23 × 0.11 × 0.08 mm

Bruker APEXII CCD area-detector diffractometer	2216 independent reflections
Radiation source: fine-focus sealed tube	1944 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 29.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→13
Tmin = 0.935, Tmax = 0.977	k = −4→6
6159 measured reflections	l = −11→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0526P)2 + 0.0105P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2216 reflections	Δρmax = 0.25 e Å−3
137 parameters	Δρmin = −0.26 e Å−3
1 restraint	Absolute structure: Flack (1983), 394 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.089 (8)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R– factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.61607 (5)	0.09862 (10)	0.21011 (5)	0.03580 (15)
O1	0.52527 (16)	−0.0799 (4)	0.25831 (16)	0.0482 (4)
O2	0.72360 (15)	0.0024 (4)	0.14799 (15)	0.0468 (4)
O3	0.27134 (16)	0.0012 (4)	0.03143 (16)	0.0469 (4)
O4	0.16275 (17)	0.2366 (4)	0.15812 (18)	0.0589 (5)
N1	0.51744 (17)	0.2853 (4)	0.11147 (16)	0.0389 (5)
H1	0.5423	0.3294	0.0426	0.047*
C1	0.6962 (2)	0.2993 (5)	0.3344 (2)	0.0366 (5)
C2	0.6546 (3)	0.2854 (7)	0.4486 (2)	0.0537 (7)
H2	0.5847	0.1687	0.4614	0.064*
C3	0.7181 (3)	0.4473 (8)	0.5441 (2)	0.0669 (9)
H3	0.6913	0.4382	0.6216	0.080*
C4	0.8199 (3)	0.6206 (8)	0.5249 (3)	0.0646 (8)
H4	0.8612	0.7303	0.5891	0.078*
C5	0.8614 (3)	0.6333 (7)	0.4113 (3)	0.0602 (7)
H5	0.9317	0.7494	0.3992	0.072*
C6	0.7990 (2)	0.4739 (5)	0.3148 (2)	0.0481 (6)
H6	0.8259	0.4843	0.2374	0.058*
C7	0.3858 (2)	0.3768 (5)	0.1419 (2)	0.0365 (5)
H7B	0.3610	0.5437	0.1008	0.044*
H7A	0.3966	0.4050	0.2309	0.044*
C8	0.2709 (2)	0.1813 (5)	0.10223 (19)	0.0346 (5)
C9	0.0435 (3)	0.0566 (10)	0.1303 (3)	0.0886 (12)
H9A	0.0132	0.0469	0.0419	0.133*
H9B	−0.0315	0.1204	0.1687	0.133*
H9C	0.0709	−0.1155	0.1619	0.133*

	U11	U22	U33	U12	U13	U23
S1	0.0316 (2)	0.0341 (3)	0.0417 (3)	−0.0008 (3)	0.00653 (19)	0.0014 (3)
O1	0.0446 (9)	0.0426 (10)	0.0565 (10)	−0.0084 (8)	0.0069 (8)	0.0094 (9)
O2	0.0390 (8)	0.0496 (11)	0.0525 (10)	0.0075 (8)	0.0099 (7)	−0.0064 (8)
O3	0.0415 (9)	0.0443 (10)	0.0559 (10)	−0.0052 (8)	0.0114 (7)	−0.0095 (9)
O4	0.0329 (8)	0.0774 (14)	0.0701 (11)	−0.0025 (9)	0.0194 (8)	−0.0181 (11)
N1	0.0333 (9)	0.0445 (12)	0.0393 (10)	−0.0014 (9)	0.0074 (8)	0.0040 (9)
C1	0.0292 (10)	0.0377 (13)	0.0412 (11)	0.0037 (9)	0.0014 (8)	0.0020 (10)
C2	0.0461 (14)	0.0662 (19)	0.0502 (14)	−0.0020 (14)	0.0123 (11)	−0.0009 (14)
C3	0.0632 (17)	0.091 (3)	0.0467 (15)	0.0050 (18)	0.0092 (13)	−0.0126 (16)
C4	0.0643 (16)	0.064 (2)	0.0587 (15)	0.0052 (18)	−0.0098 (12)	−0.0190 (18)
C5	0.0537 (14)	0.051 (2)	0.0701 (16)	−0.0110 (15)	−0.0044 (12)	−0.0030 (16)
C6	0.0469 (13)	0.0451 (16)	0.0518 (14)	−0.0052 (12)	0.0071 (11)	0.0017 (12)
C7	0.0352 (11)	0.0327 (13)	0.0423 (11)	0.0031 (10)	0.0082 (9)	0.0019 (10)
C8	0.0295 (10)	0.0394 (14)	0.0342 (10)	0.0059 (9)	0.0038 (8)	0.0031 (10)
C9	0.0397 (14)	0.116 (3)	0.114 (3)	−0.0180 (19)	0.0257 (16)	−0.015 (3)

S1—O1	1.4290 (16)	C3—C4	1.369 (4)
S1—O2	1.4291 (15)	C3—H3	0.9300
S1—N1	1.618 (2)	C4—C5	1.372 (4)
S1—C1	1.767 (2)	C4—H4	0.9300
O3—C8	1.198 (3)	C5—C6	1.383 (4)
O4—C8	1.336 (2)	C5—H5	0.9300
O4—C9	1.466 (4)	C6—H6	0.9300
N1—C7	1.454 (3)	C7—C8	1.501 (3)
N1—H1	0.8600	C7—H7B	0.9700
C1—C2	1.380 (3)	C7—H7A	0.9700
C1—C6	1.381 (3)	C9—H9A	0.9600
C2—C3	1.386 (4)	C9—H9B	0.9600
C2—H2	0.9300	C9—H9C	0.9600
O1—S1—O2	120.61 (11)	C4—C5—C6	120.2 (3)
O1—S1—N1	106.53 (9)	C4—C5—H5	119.9
O2—S1—N1	106.36 (9)	C6—C5—H5	119.9
O1—S1—C1	107.48 (10)	C1—C6—C5	119.4 (2)
O2—S1—C1	107.55 (10)	C1—C6—H6	120.3
N1—S1—C1	107.73 (10)	C5—C6—H6	120.3
C8—O4—C9	115.6 (2)	N1—C7—C8	111.31 (18)
C7—N1—S1	118.54 (14)	N1—C7—H7B	109.4
C7—N1—H1	120.7	C8—C7—H7B	109.4
S1—N1—H1	120.7	N1—C7—H7A	109.4
C2—C1—C6	120.6 (2)	C8—C7—H7A	109.4
C2—C1—S1	120.4 (2)	H7B—C7—H7A	108.0
C6—C1—S1	119.01 (17)	O3—C8—O4	123.2 (2)
C1—C2—C3	119.2 (3)	O3—C8—C7	127.20 (19)
C1—C2—H2	120.4	O4—C8—C7	109.60 (19)
C3—C2—H2	120.4	O4—C9—H9A	109.5
C4—C3—C2	120.3 (3)	O4—C9—H9B	109.5
C4—C3—H3	119.8	H9A—C9—H9B	109.5
C2—C3—H3	119.8	O4—C9—H9C	109.5
C3—C4—C5	120.3 (3)	H9A—C9—H9C	109.5
C3—C4—H4	119.9	H9B—C9—H9C	109.5
C5—C4—H4	119.9
O1—S1—N1—C7	40.2 (2)	C1—C2—C3—C4	0.6 (5)
O2—S1—N1—C7	170.05 (17)	C2—C3—C4—C5	−0.8 (5)
C1—S1—N1—C7	−74.87 (19)	C3—C4—C5—C6	1.0 (5)
O1—S1—C1—C2	−7.1 (2)	C2—C1—C6—C5	0.8 (4)
O2—S1—C1—C2	−138.4 (2)	S1—C1—C6—C5	179.5 (2)
N1—S1—C1—C2	107.3 (2)	C4—C5—C6—C1	−1.0 (4)
O1—S1—C1—C6	174.20 (18)	S1—N1—C7—C8	−86.9 (2)
O2—S1—C1—C6	42.9 (2)	C9—O4—C8—O3	1.7 (3)
N1—S1—C1—C6	−71.3 (2)	C9—O4—C8—C7	−178.5 (2)
C6—C1—C2—C3	−0.6 (4)	N1—C7—C8—O3	−15.8 (3)
S1—C1—C2—C3	−179.2 (2)	N1—C7—C8—O4	164.42 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	2.28	2.998 (2)	141
C7—H7B···O3ii	0.97	2.55	3.503 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.28	2.998 (2)	141
C7—H7B⋯O3ii	0.97	2.55	3.503 (4)	168

Symmetry codes: (i) ; (ii) .