Methyl (4-bromo-benzene-sulfonamido)acetate.

The title compound, C(9)H(10)BrNO(4)S, is an inter-mediate for the formation of benzothia-zines. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules, forming R(2) (2)(10) ring motifs, which are linked into a two-dimensional polymeric sheet through inter-molecular 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 = 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

Δρmax = 0.53 e Å−3

Δρmin = −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.

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

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

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

C9H10BrNO4S	Z = 2
Mr = 308.15	F000 = 308
Triclinic, P1	Dx = 1.767 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.0451 (2) Å	Cell parameters from 2846 reflections
b = 7.0369 (2) Å	θ = 1.5–28.3º
c = 13.8695 (5) Å	µ = 3.73 mm−1
α = 83.866 (2)º	T = 296 (2) K
β = 81.190 (1)º	Prism, colorless
γ = 87.027 (2)º	0.23 × 0.18 × 0.12 mm
V = 579.31 (3) Å3

Bruker Kappa APEXII CCD diffractometer	2846 independent reflections
Radiation source: fine-focus sealed tube	1893 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
Detector resolution: 7.40 pixels mm-1	θmax = 28.3º
T = 296(2) K	θmin = 1.5º
ω scans	h = −8→8
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.449, Tmax = 0.639	l = −18→18
13148 measured reflections

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.5395P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2846 reflections	Δρmax = 0.53 e Å−3
145 parameters	Δρmin = −0.59 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Br1	0.31108 (8)	0.18201 (7)	0.47759 (3)	0.0859 (2)
S1	−0.15899 (12)	0.80316 (11)	0.19808 (6)	0.0428 (2)
O1	0.4939 (4)	0.7999 (3)	−0.06466 (17)	0.0535 (6)
O2	0.2102 (5)	0.6116 (4)	−0.06458 (19)	0.0694 (8)
O3	−0.3871 (3)	0.7563 (4)	0.20253 (19)	0.0589 (6)
O4	−0.1032 (4)	0.9893 (3)	0.21559 (19)	0.0602 (6)
N1	−0.0358 (4)	0.7668 (4)	0.08966 (18)	0.0426 (6)
H1	−0.1060	0.7168	0.0497	0.051*
C1	0.6104 (7)	0.7313 (6)	−0.1532 (3)	0.0720 (12)
H1A	0.7505	0.7935	−0.1714	0.108*
H1B	0.5207	0.7589	−0.2048	0.108*
H1C	0.6379	0.5957	−0.1425	0.108*
C2	0.2962 (5)	0.7298 (4)	−0.0293 (2)	0.0411 (7)
C3	0.1966 (5)	0.8203 (5)	0.0605 (2)	0.0427 (7)
H3A	0.2818	0.7791	0.1133	0.051*
H3B	0.2032	0.9583	0.0477	0.051*
C4	−0.0381 (5)	0.6363 (4)	0.2804 (2)	0.0385 (6)
C5	−0.1158 (6)	0.4529 (5)	0.2982 (2)	0.0482 (8)
H5	−0.2363	0.4206	0.2696	0.058*
C6	−0.0151 (6)	0.3180 (5)	0.3582 (2)	0.0534 (8)
H6	−0.0672	0.1944	0.3709	0.064*
C7	0.1645 (6)	0.3690 (6)	0.3992 (2)	0.0528 (9)
C8	0.2420 (6)	0.5515 (6)	0.3828 (3)	0.0549 (9)
H8	0.3625	0.5834	0.4115	0.066*
C9	0.1398 (5)	0.6868 (5)	0.3233 (2)	0.0484 (8)
H9	0.1898	0.8111	0.3121	0.058*

	U11	U22	U33	U12	U13	U23
Br1	0.0822 (3)	0.1005 (4)	0.0689 (3)	0.0267 (3)	−0.0172 (2)	0.0133 (2)
S1	0.0313 (4)	0.0443 (5)	0.0512 (5)	−0.0016 (3)	−0.0027 (3)	−0.0019 (3)
O1	0.0403 (12)	0.0621 (15)	0.0588 (14)	−0.0191 (10)	0.0057 (10)	−0.0201 (12)
O2	0.0744 (17)	0.0703 (18)	0.0649 (16)	−0.0429 (14)	0.0103 (13)	−0.0240 (14)
O3	0.0288 (11)	0.0740 (17)	0.0704 (16)	−0.0032 (10)	−0.0048 (10)	0.0059 (13)
O4	0.0603 (15)	0.0420 (14)	0.0770 (18)	0.0016 (11)	−0.0034 (13)	−0.0112 (12)
N1	0.0335 (13)	0.0531 (16)	0.0423 (14)	−0.0158 (11)	−0.0078 (10)	0.0004 (12)
C1	0.060 (2)	0.078 (3)	0.076 (3)	−0.016 (2)	0.020 (2)	−0.031 (2)
C2	0.0409 (16)	0.0361 (16)	0.0465 (17)	−0.0116 (12)	−0.0062 (13)	−0.0003 (13)
C3	0.0363 (16)	0.0476 (18)	0.0453 (17)	−0.0140 (13)	−0.0052 (12)	−0.0053 (14)
C4	0.0320 (14)	0.0470 (17)	0.0359 (15)	−0.0035 (12)	−0.0008 (11)	−0.0067 (13)
C5	0.0478 (18)	0.052 (2)	0.0467 (18)	−0.0114 (15)	−0.0110 (14)	−0.0048 (15)
C6	0.061 (2)	0.050 (2)	0.0488 (19)	−0.0070 (16)	−0.0077 (16)	−0.0017 (15)
C7	0.0484 (19)	0.071 (2)	0.0348 (16)	0.0117 (17)	0.0007 (14)	−0.0016 (15)
C8	0.0398 (17)	0.076 (3)	0.050 (2)	−0.0057 (16)	−0.0110 (14)	−0.0062 (18)
C9	0.0386 (17)	0.055 (2)	0.0524 (19)	−0.0110 (14)	−0.0041 (14)	−0.0102 (16)

Br1—C7	1.889 (3)	C3—N1	1.458 (4)
S1—O4	1.424 (2)	C3—H3A	0.9700
S1—O3	1.425 (2)	C3—H3B	0.9700
S1—N1	1.613 (3)	C4—C5	1.381 (4)
S1—C4	1.759 (3)	C4—C9	1.385 (4)
O1—C2	1.320 (3)	C5—C6	1.374 (5)
O1—C1	1.436 (4)	C5—H5	0.9300
O2—C2	1.188 (4)	C6—C7	1.381 (5)
N1—H1	0.8600	C6—H6	0.9300
C1—H1A	0.9600	C7—C8	1.374 (5)
C1—H1B	0.9600	C8—C9	1.377 (5)
C1—H1C	0.9600	C8—H8	0.9300
C2—C3	1.489 (4)	C9—H9	0.9300
O4—S1—O3	120.49 (15)	N1—C3—H3B	109.6
O4—S1—N1	106.96 (14)	C2—C3—H3B	109.6
O3—S1—N1	106.53 (14)	H3A—C3—H3B	108.1
O4—S1—C4	107.89 (15)	C5—C4—C9	120.5 (3)
O3—S1—C4	107.66 (14)	C5—C4—S1	119.4 (2)
N1—S1—C4	106.55 (14)	C9—C4—S1	120.1 (2)
C2—O1—C1	117.5 (3)	C6—C5—C4	120.1 (3)
C3—N1—S1	118.9 (2)	C6—C5—H5	120.0
C3—N1—H1	120.6	C4—C5—H5	120.0
S1—N1—H1	120.6	C5—C6—C7	118.9 (3)
O1—C1—H1A	109.5	C5—C6—H6	120.6
O1—C1—H1B	109.5	C7—C6—H6	120.6
H1A—C1—H1B	109.5	C8—C7—C6	121.6 (3)
O1—C1—H1C	109.5	C8—C7—Br1	119.2 (3)
H1A—C1—H1C	109.5	C6—C7—Br1	119.2 (3)
H1B—C1—H1C	109.5	C7—C8—C9	119.4 (3)
O2—C2—O1	124.5 (3)	C7—C8—H8	120.3
O2—C2—C3	125.0 (3)	C9—C8—H8	120.3
O1—C2—C3	110.4 (2)	C8—C9—C4	119.5 (3)
N1—C3—C2	110.1 (2)	C8—C9—H9	120.2
N1—C3—H3A	109.6	C4—C9—H9	120.2
C2—C3—H3A	109.6
C1—O1—C2—O2	1.4 (5)	C4—C5—C6—C7	−0.4 (5)
C1—O1—C2—C3	−178.3 (3)	C5—C6—C7—C8	1.1 (5)
O2—C2—C3—N1	−9.3 (5)	C5—C6—C7—Br1	−177.6 (3)
O1—C2—C3—N1	170.5 (3)	C6—C7—C8—C9	−0.5 (5)
O4—S1—C4—C5	162.0 (2)	Br1—C7—C8—C9	178.1 (2)
O3—S1—C4—C5	30.5 (3)	C7—C8—C9—C4	−0.6 (5)
N1—S1—C4—C5	−83.4 (3)	C5—C4—C9—C8	1.2 (5)
O4—S1—C4—C9	−20.8 (3)	S1—C4—C9—C8	−175.9 (2)
O3—S1—C4—C9	−152.3 (3)	C2—C3—N1—S1	165.0 (2)
N1—S1—C4—C9	93.7 (3)	O4—S1—N1—C3	44.2 (3)
C9—C4—C5—C6	−0.7 (5)	O3—S1—N1—C3	174.3 (2)
S1—C4—C5—C6	176.5 (3)	C4—S1—N1—C3	−71.0 (3)

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

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

Symmetry codes: (i) ; (ii) .