2-(4-Bromo-benzene-sulfonamido)acetic acid.

The title compound, C(8)H(8)BrNO(4)S, a halogenated sulfon-amide, was prepared by basic hydrolysis of the methyl ester. In the crystal, mol-ecules form centrosymmetric hydrogen-bonded dimers via the carboxyl groups. These dimers are further linked by N-H⋯O inter-actions involving the carbonyl O and amide H atoms, forming a ribbon-like structure propagating in [010]. These ribbons are further linked via C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For details of the crystal structure of the methyl ester of the title compound, see: Arshad et al. (2008b ▶). For related structures, see: Arshad et al. (2008a ▶); Arshad et al. (2009 ▶). For related thia­zine heterocycles, see: Arshad et al. (2008c ▶). For hydrogen-bonding patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H8BrNO4S

M = 294.12

Triclinic,

a = 5.0042 (4) Å

b = 7.9997 (6) Å

c = 13.2289 (11) Å

α = 79.691 (4)°

β = 88.667 (5)°

γ = 81.404 (4)°

V = 515.18 (7) Å3

Z = 2

Mo Kα radiation

μ = 4.18 mm−1

T = 296 K

0.28 × 0.17 × 0.11 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.612, T max = 0.632

10359 measured reflections

2557 independent reflections

1243 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.168

S = 0.95

2557 reflections

137 parameters

H-atom parameters constrained

Δρmax = 1.15 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680902604X/tk2493sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680902604X/tk2493Isup2.hkl

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

C8H8BrNO4S	Z = 2
Mr = 294.12	F(000) = 292
Triclinic, P1	Dx = 1.896 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0042 (4) Å	Cell parameters from 1869 reflections
b = 7.9997 (6) Å	θ = 2.2–21.8°
c = 13.2289 (11) Å	µ = 4.18 mm−1
α = 79.691 (4)°	T = 296 K
β = 88.667 (5)°	Needle, colorless
γ = 81.404 (4)°	0.28 × 0.17 × 0.11 mm
V = 515.18 (7) Å3

Bruker Kappa APEXII CCD diffractometer	2557 independent reflections
Radiation source: fine-focus sealed tube	1243 reflections with I > 2σ(I)
graphite	Rint = 0.056
φ and ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −6→6
Tmin = 0.612, Tmax = 0.632	k = −10→10
10359 measured reflections	l = −17→17

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0872P)2 + 0.2177P] where P = (Fo2 + 2Fc2)/3
2557 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 1.15 e Å−3
0 restraints	Δρmin = −0.38 e Å−3

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	0.70371 (17)	0.78972 (8)	0.05167 (5)	0.0774 (4)
S1	0.3354 (2)	0.11701 (17)	0.32101 (10)	0.0365 (4)
O1	0.2650 (7)	0.0106 (5)	0.2528 (3)	0.0486 (10)
O2	0.1387 (7)	0.1738 (5)	0.3930 (3)	0.0492 (10)
O3	0.7775 (7)	−0.4424 (5)	0.4169 (3)	0.0505 (10)
H3O	0.7174	−0.5221	0.4536	0.076*
O4	0.4156 (7)	−0.2871 (4)	0.4743 (3)	0.0427 (9)
N1	0.5998 (8)	0.0162 (5)	0.3816 (3)	0.0389 (10)
H1	0.6632	0.0630	0.4278	0.047*
C1	0.5927 (12)	0.5917 (7)	0.1309 (4)	0.0456 (14)
C2	0.3808 (12)	0.6089 (7)	0.1979 (5)	0.0495 (15)
H2	0.2914	0.7172	0.2039	0.059*
C3	0.3022 (11)	0.4635 (7)	0.2560 (5)	0.0453 (14)
H3	0.1575	0.4737	0.3010	0.054*
C4	0.4368 (10)	0.3039 (7)	0.2478 (4)	0.0355 (12)
C5	0.6490 (11)	0.2867 (7)	0.1801 (4)	0.0489 (15)
H5	0.7386	0.1784	0.1742	0.059*
C6	0.7271 (13)	0.4320 (8)	0.1211 (5)	0.0584 (17)
H6	0.8695	0.4221	0.0751	0.070*
C7	0.7389 (10)	−0.1470 (6)	0.3652 (4)	0.0410 (13)
H7A	0.9274	−0.1559	0.3839	0.049*
H7B	0.7316	−0.1519	0.2925	0.049*
C8	0.6253 (10)	−0.2978 (7)	0.4249 (4)	0.0368 (12)

	U11	U22	U33	U12	U13	U23
Br1	0.1144 (7)	0.0372 (4)	0.0728 (6)	−0.0176 (4)	0.0098 (4)	0.0154 (3)
S1	0.0376 (7)	0.0264 (7)	0.0458 (8)	−0.0085 (5)	0.0029 (5)	−0.0043 (6)
O1	0.053 (2)	0.037 (2)	0.060 (3)	−0.0124 (18)	−0.0073 (18)	−0.0143 (19)
O2	0.045 (2)	0.046 (2)	0.058 (2)	−0.0118 (18)	0.0163 (18)	−0.011 (2)
O3	0.050 (2)	0.027 (2)	0.069 (3)	0.0001 (18)	0.0167 (19)	−0.001 (2)
O4	0.0398 (19)	0.027 (2)	0.059 (2)	−0.0058 (16)	0.0127 (17)	−0.0008 (17)
N1	0.050 (2)	0.019 (2)	0.046 (3)	−0.0062 (19)	−0.002 (2)	−0.001 (2)
C1	0.064 (4)	0.026 (3)	0.044 (3)	−0.009 (3)	−0.004 (3)	0.002 (3)
C2	0.059 (3)	0.017 (3)	0.068 (4)	0.003 (3)	0.000 (3)	−0.006 (3)
C3	0.045 (3)	0.025 (3)	0.065 (4)	−0.002 (2)	0.008 (3)	−0.007 (3)
C4	0.041 (3)	0.027 (3)	0.038 (3)	−0.003 (2)	−0.001 (2)	−0.005 (2)
C5	0.064 (4)	0.022 (3)	0.054 (4)	0.001 (3)	0.013 (3)	0.004 (3)
C6	0.073 (4)	0.040 (4)	0.054 (4)	−0.001 (3)	0.021 (3)	0.006 (3)
C7	0.039 (3)	0.032 (3)	0.049 (3)	−0.010 (2)	0.009 (2)	0.001 (3)
C8	0.035 (3)	0.033 (3)	0.042 (3)	−0.007 (2)	0.000 (2)	−0.003 (2)

Br1—C1	1.886 (5)	C2—C3	1.379 (7)
S1—O1	1.429 (4)	C2—H2	0.9300
S1—O2	1.436 (4)	C3—C4	1.374 (7)
S1—N1	1.594 (4)	C3—H3	0.9300
S1—C4	1.765 (5)	C4—C5	1.380 (7)
O3—C8	1.306 (6)	C5—C6	1.382 (7)
O3—H3O	0.8200	C5—H5	0.9300
O4—C8	1.223 (6)	C6—H6	0.9300
N1—C7	1.436 (6)	C7—C8	1.499 (6)
N1—H1	0.8600	C7—H7A	0.9700
C1—C2	1.373 (8)	C7—H7B	0.9700
C1—C6	1.379 (8)
O1—S1—O2	119.3 (2)	C3—C4—C5	120.5 (5)
O1—S1—N1	106.7 (2)	C3—C4—S1	120.6 (4)
O2—S1—N1	109.3 (2)	C5—C4—S1	118.9 (4)
O1—S1—C4	108.9 (2)	C4—C5—C6	119.4 (5)
O2—S1—C4	106.5 (2)	C4—C5—H5	120.3
N1—S1—C4	105.3 (2)	C6—C5—H5	120.3
C8—O3—H3O	109.5	C1—C6—C5	119.6 (5)
C7—N1—S1	124.8 (4)	C1—C6—H6	120.2
C7—N1—H1	117.6	C5—C6—H6	120.2
S1—N1—H1	117.5	N1—C7—C8	113.8 (4)
C2—C1—C6	121.0 (5)	N1—C7—H7A	108.8
C2—C1—Br1	119.6 (4)	C8—C7—H7A	108.8
C6—C1—Br1	119.4 (4)	N1—C7—H7B	108.8
C1—C2—C3	119.2 (5)	C8—C7—H7B	108.8
C1—C2—H2	120.4	H7A—C7—H7B	107.7
C3—C2—H2	120.4	O4—C8—O3	124.3 (5)
C4—C3—C2	120.2 (5)	O4—C8—C7	124.4 (5)
C4—C3—H3	119.9	O3—C8—C7	111.4 (4)
C2—C3—H3	119.9
O1—S1—N1—C7	2.2 (4)	O1—S1—C4—C5	−57.6 (5)
O2—S1—N1—C7	132.5 (4)	O2—S1—C4—C5	172.6 (4)
C4—S1—N1—C7	−113.5 (4)	N1—S1—C4—C5	56.6 (5)
C6—C1—C2—C3	0.0 (9)	C3—C4—C5—C6	0.6 (9)
Br1—C1—C2—C3	−179.5 (4)	S1—C4—C5—C6	178.9 (5)
C1—C2—C3—C4	0.8 (9)	C2—C1—C6—C5	−0.5 (10)
C2—C3—C4—C5	−1.1 (8)	Br1—C1—C6—C5	179.1 (5)
C2—C3—C4—S1	−179.4 (4)	C4—C5—C6—C1	0.2 (9)
O1—S1—C4—C3	120.7 (5)	S1—N1—C7—C8	−85.5 (5)
O2—S1—C4—C3	−9.1 (5)	N1—C7—C8—O4	8.2 (8)
N1—S1—C4—C3	−125.2 (5)	N1—C7—C8—O3	−172.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4i	0.82	1.85	2.671 (5)	174
N1—H1···O4ii	0.86	2.38	3.124 (5)	146
C2—H2···O1iii	0.93	2.53	3.384 (7)	153
C3—H3···O3iv	0.93	2.50	3.423 (7)	170
C3—H3···O2	0.93	2.50	2.884 (7)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4i	0.82	1.85	2.671 (5)	174
N1—H1⋯O4ii	0.86	2.38	3.124 (5)	146
C2—H2⋯O1iii	0.93	2.53	3.384 (7)	153
C3—H3⋯O3iv	0.93	2.50	3.423 (7)	170

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .