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

In the title compound, C(13)H(10)BrNO(4)S, the dihedral angle between the benzene rings is 82.75 (15)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal structure, two mol-ecules form an R(2) (2)(8) centrosymmetric dimer through a pair of O-H⋯O hydrogen bonds. Intra- and inter-molecular C-H⋯O hydrogen bonds are also observed.

Related literature

For background to sulfonamide derivatives, see: Allison et al. (2006 ▶); Sheppard et al. (2006 ▶). For related structures, see: Arshad et al. (2009 ▶); Shafiq et al. (2009 ▶); Asiri et al. (2009 ▶). For hydrogen-bond graph-set terminology, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C13H10BrNO4S

M = 356.19

Monoclinic,

a = 27.8316 (11) Å

b = 8.5684 (4) Å

c = 11.6632 (5) Å

β = 98.196 (2)°

V = 2752.9 (2) Å3

Z = 8

Mo Kα radiation

μ = 3.15 mm−1

T = 296 K

0.23 × 0.19 × 0.11 mm

Data collection

Bruker Kappa-APEXII CCD area-detector diffractometer

Absorption correction: refined from ΔF [Cubic fit to sin(θ)/λ - 24 parameters; Parkin et al., 1995 ▶] T min = 0.497, T max = 0.707

14822 measured reflections

3416 independent reflections

1764 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.093

S = 0.98

3416 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022545/is2431sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022545/is2431Isup2.hkl

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

C13H10BrNO4S	F(000) = 1424
Mr = 356.19	Dx = 1.719 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3121 reflections
a = 27.8316 (11) Å	θ = 2.5–22.0°
b = 8.5684 (4) Å	µ = 3.15 mm−1
c = 11.6632 (5) Å	T = 296 K
β = 98.196 (2)°	Block, dark brown
V = 2752.9 (2) Å3	0.23 × 0.19 × 0.11 mm
Z = 8

Bruker Kappa-APEXII CCD area-detector diffractometer	3416 independent reflections
Radiation source: sealed tube	1764 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 28.3°, θmin = 2.5°
Absorption correction: part of the refinement model (ΔF) [Cubic fit to sin(θ)/λ - 24 parameters; Parkin et al., 1995]	h = −37→36
Tmin = 0.497, Tmax = 0.707	k = −11→11
14822 measured reflections	l = −15→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.033P)2 + 1.5317P] where P = (Fo2 + 2Fc2)/3
3416 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > σ(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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	0.81917 (1)	0.43825 (6)	0.51473 (4)	0.1153 (2)
S1	0.62425 (3)	0.44674 (8)	0.15544 (6)	0.0547 (2)
O1	0.53281 (7)	0.4722 (2)	0.39261 (16)	0.0628 (7)
O2	0.50891 (7)	0.2889 (2)	0.50674 (17)	0.0721 (8)
O3	0.61345 (8)	0.6071 (2)	0.13563 (17)	0.0713 (8)
O4	0.63014 (7)	0.3473 (2)	0.06120 (15)	0.0665 (7)
N1	0.58022 (7)	0.3824 (2)	0.22029 (18)	0.0555 (8)
C1	0.67716 (9)	0.4336 (3)	0.2571 (2)	0.0514 (9)
C2	0.71403 (11)	0.3319 (3)	0.2413 (3)	0.0659 (11)
C3	0.75605 (11)	0.3324 (4)	0.3185 (3)	0.0788 (14)
C4	0.76082 (11)	0.4310 (4)	0.4111 (3)	0.0705 (11)
C5	0.72375 (12)	0.5304 (4)	0.4281 (3)	0.0782 (14)
C6	0.68182 (12)	0.5303 (4)	0.3517 (3)	0.0714 (12)
C7	0.57612 (8)	0.2291 (3)	0.2636 (2)	0.0488 (9)
C8	0.55269 (8)	0.2054 (3)	0.3611 (2)	0.0505 (9)
C9	0.54903 (10)	0.0538 (4)	0.4003 (3)	0.0685 (11)
C10	0.56676 (11)	−0.0710 (4)	0.3463 (3)	0.0788 (14)
C11	0.58873 (11)	−0.0459 (3)	0.2499 (3)	0.0726 (11)
C12	0.59331 (10)	0.1022 (3)	0.2086 (3)	0.0606 (10)
C13	0.53137 (9)	0.3347 (4)	0.4206 (2)	0.0562 (10)
H1	0.55740	0.44700	0.22910	0.0670*
H2	0.71040	0.26350	0.17880	0.0790*
H2A	0.49850	0.36530	0.53760	0.1080*
H3	0.78130	0.26550	0.30760	0.0940*
H5	0.72720	0.59740	0.49150	0.0940*
H6	0.65640	0.59580	0.36380	0.0860*
H9	0.53410	0.03640	0.46550	0.0820*
H10	0.56390	−0.17150	0.37460	0.0940*
H11	0.60060	−0.13020	0.21220	0.0870*
H12	0.60810	0.11760	0.14300	0.0730*

	U11	U22	U33	U12	U13	U23
Br1	0.0724 (2)	0.1642 (5)	0.1042 (4)	−0.0277 (2)	−0.0048 (2)	0.0332 (3)
S1	0.0662 (4)	0.0525 (4)	0.0493 (4)	0.0040 (3)	0.0221 (3)	0.0044 (3)
O1	0.0667 (12)	0.0678 (13)	0.0586 (12)	0.0035 (10)	0.0251 (10)	0.0005 (10)
O2	0.0768 (13)	0.0831 (13)	0.0641 (13)	−0.0003 (11)	0.0362 (11)	0.0049 (11)
O3	0.0920 (14)	0.0549 (12)	0.0700 (14)	0.0115 (10)	0.0218 (11)	0.0149 (10)
O4	0.0860 (13)	0.0710 (12)	0.0478 (11)	−0.0033 (10)	0.0273 (10)	−0.0051 (10)
N1	0.0548 (12)	0.0553 (13)	0.0600 (15)	0.0105 (10)	0.0206 (11)	0.0067 (11)
C1	0.0595 (15)	0.0492 (15)	0.0499 (16)	−0.0006 (12)	0.0226 (13)	0.0021 (13)
C2	0.0743 (19)	0.0599 (18)	0.066 (2)	0.0077 (15)	0.0182 (16)	−0.0043 (15)
C3	0.069 (2)	0.084 (2)	0.086 (3)	0.0129 (17)	0.0198 (19)	0.006 (2)
C4	0.0598 (17)	0.089 (2)	0.064 (2)	−0.0170 (17)	0.0137 (15)	0.0162 (18)
C5	0.076 (2)	0.100 (3)	0.061 (2)	−0.0116 (19)	0.0177 (18)	−0.0176 (18)
C6	0.074 (2)	0.079 (2)	0.065 (2)	0.0075 (16)	0.0227 (17)	−0.0166 (17)
C7	0.0403 (13)	0.0554 (16)	0.0510 (16)	−0.0008 (11)	0.0079 (12)	−0.0010 (13)
C8	0.0388 (12)	0.0612 (17)	0.0529 (16)	−0.0032 (12)	0.0112 (11)	0.0012 (14)
C9	0.0602 (17)	0.073 (2)	0.077 (2)	−0.0094 (15)	0.0259 (16)	0.0083 (18)
C10	0.074 (2)	0.0595 (19)	0.106 (3)	−0.0088 (16)	0.024 (2)	0.0123 (19)
C11	0.076 (2)	0.0557 (19)	0.090 (2)	−0.0043 (15)	0.0251 (18)	−0.0065 (17)
C12	0.0607 (17)	0.0576 (18)	0.0665 (19)	−0.0056 (13)	0.0196 (14)	−0.0032 (15)
C13	0.0402 (13)	0.080 (2)	0.0490 (16)	−0.0046 (13)	0.0080 (12)	0.0015 (15)

Br1—C4	1.882 (3)	C7—C12	1.382 (4)
S1—O3	1.4184 (19)	C7—C8	1.404 (3)
S1—O4	1.4186 (19)	C8—C13	1.476 (4)
S1—N1	1.625 (2)	C8—C9	1.386 (4)
S1—C1	1.758 (3)	C9—C10	1.368 (5)
O1—C13	1.225 (4)	C10—C11	1.371 (5)
O2—C13	1.317 (3)	C11—C12	1.370 (4)
O2—H2A	0.8200	C2—H2	0.9300
N1—C7	1.418 (3)	C3—H3	0.9300
N1—H1	0.8600	C5—H5	0.9300
C1—C6	1.371 (4)	C6—H6	0.9300
C1—C2	1.379 (4)	C9—H9	0.9300
C2—C3	1.371 (5)	C10—H10	0.9300
C3—C4	1.363 (5)	C11—H11	0.9300
C4—C5	1.374 (5)	C12—H12	0.9300
C5—C6	1.364 (5)
Br1···C9i	3.662 (3)	C12···O4	2.987 (3)
Br1···C10i	3.540 (3)	C13···N1vi	3.325 (3)
Br1···C11i	3.599 (3)	C13···O3iii	3.182 (3)
S1···H12	2.8600	C13···C7vi	3.543 (3)
O1···N1	2.670 (3)	C2···H5v	3.0500
O1···O2ii	2.703 (3)	C5···H2ix	3.0900
O2···O3iii	3.205 (3)	C6···H3ix	3.0200
O2···O1ii	2.703 (3)	C9···H9vii	3.0700
O3···C11iv	3.369 (3)	C13···H1	2.6300
O3···C13v	3.182 (3)	C13···H1vi	2.9700
O3···O2v	3.205 (3)	C13···H2Aii	2.7700
O4···C6v	3.185 (4)	H1···O1	2.1300
O4···C5v	3.384 (4)	H1···C13	2.6300
O4···C12	2.987 (3)	H1···O1vi	2.7100
O1···H1	2.1300	H1···C13vi	2.9700
O1···H2Aii	1.8900	H2···O4	2.5500
O1···H1vi	2.7100	H2···H5v	2.5900
O2···H9	2.3500	H2···C5x	3.0900
O2···H10vii	2.8000	H2A···O1ii	1.8900
O3···H11iv	2.4700	H2A···C13ii	2.7700
O3···H6	2.7600	H2A···H2Aii	2.4700
O4···H12	2.3100	H3···C6x	3.0200
O4···H2	2.5500	H5···C2iii	3.0500
O4···H6v	2.5600	H5···H2iii	2.5900
N1···O1	2.670 (3)	H6···O3	2.7600
N1···C13vi	3.325 (3)	H6···O4iii	2.5600
C5···O4iii	3.384 (4)	H9···O2	2.3500
C6···O4iii	3.185 (4)	H9···C9vii	3.0700
C7···C13vi	3.543 (3)	H9···H9vii	2.2500
C9···Br1i	3.661 (3)	H10···O2vii	2.8000
C10···Br1i	3.540 (3)	H11···O3viii	2.4700
C11···Br1i	3.599 (3)	H12···S1	2.8600
C11···O3viii	3.369 (3)	H12···O4	2.3100
O3—S1—O4	120.06 (12)	C9—C8—C13	119.7 (2)
O3—S1—N1	104.36 (12)	C8—C9—C10	122.2 (3)
O3—S1—C1	108.04 (13)	C9—C10—C11	119.2 (3)
O4—S1—N1	109.57 (11)	C10—C11—C12	120.6 (3)
O4—S1—C1	107.82 (12)	C7—C12—C11	120.7 (3)
N1—S1—C1	106.21 (11)	O1—C13—O2	121.8 (3)
C13—O2—H2A	109.00	O1—C13—C8	124.5 (2)
S1—N1—C7	125.76 (16)	O2—C13—C8	113.7 (3)
C7—N1—H1	117.00	C1—C2—H2	120.00
S1—N1—H1	117.00	C3—C2—H2	120.00
S1—C1—C2	121.2 (2)	C2—C3—H3	120.00
S1—C1—C6	118.6 (2)	C4—C3—H3	120.00
C2—C1—C6	120.2 (3)	C4—C5—H5	120.00
C1—C2—C3	119.5 (3)	C6—C5—H5	120.00
C2—C3—C4	120.0 (3)	C1—C6—H6	120.00
Br1—C4—C3	120.5 (2)	C5—C6—H6	120.00
Br1—C4—C5	118.9 (3)	C8—C9—H9	119.00
C3—C4—C5	120.6 (3)	C10—C9—H9	119.00
C4—C5—C6	119.7 (3)	C9—C10—H10	120.00
C1—C6—C5	120.0 (3)	C11—C10—H10	120.00
C8—C7—C12	119.6 (2)	C10—C11—H11	120.00
N1—C7—C12	120.9 (2)	C12—C11—H11	120.00
N1—C7—C8	119.5 (2)	C7—C12—H12	120.00
C7—C8—C9	117.9 (2)	C11—C12—H12	120.00
C7—C8—C13	122.5 (2)
O3—S1—N1—C7	−176.5 (2)	Br1—C4—C5—C6	177.9 (3)
O4—S1—N1—C7	53.8 (2)	C3—C4—C5—C6	0.0 (5)
C1—S1—N1—C7	−62.4 (2)	C4—C5—C6—C1	−1.3 (5)
O3—S1—C1—C2	−135.0 (2)	N1—C7—C8—C9	179.5 (2)
O4—S1—C1—C2	−3.8 (3)	N1—C7—C8—C13	0.7 (3)
N1—S1—C1—C2	113.6 (2)	C12—C7—C8—C9	1.8 (4)
O3—S1—C1—C6	43.2 (3)	C12—C7—C8—C13	−177.0 (2)
O4—S1—C1—C6	174.3 (2)	N1—C7—C12—C11	−179.2 (3)
N1—S1—C1—C6	−68.3 (3)	C8—C7—C12—C11	−1.6 (4)
S1—N1—C7—C8	149.12 (19)	C7—C8—C9—C10	−0.9 (4)
S1—N1—C7—C12	−33.3 (3)	C13—C8—C9—C10	177.9 (3)
S1—C1—C6—C5	−175.6 (3)	C7—C8—C13—O1	−1.4 (4)
S1—C1—C2—C3	175.7 (2)	C7—C8—C13—O2	176.9 (2)
C6—C1—C2—C3	−2.4 (4)	C9—C8—C13—O1	179.9 (3)
C2—C1—C6—C5	2.5 (5)	C9—C8—C13—O2	−1.9 (3)
C1—C2—C3—C4	1.1 (5)	C8—C9—C10—C11	−0.3 (5)
C2—C3—C4—C5	0.1 (5)	C9—C10—C11—C12	0.6 (5)
C2—C3—C4—Br1	−177.7 (2)	C10—C11—C12—C7	0.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	2.13	2.670 (3)	121
O2—H2A···O1ii	0.82	1.89	2.703 (3)	173
C6—H6···O4iii	0.93	2.56	3.185 (4)	125
C11—H11···O3viii	0.93	2.47	3.369 (3)	164
C12—H12···O4	0.93	2.31	2.987 (3)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	2.13	2.670 (3)	121
O2—H2A⋯O1i	0.82	1.89	2.703 (3)	173
C6—H6⋯O4ii	0.93	2.56	3.185 (4)	125
C11—H11⋯O3iii	0.93	2.47	3.369 (3)	164
C12—H12⋯O4	0.93	2.31	2.987 (3)	130

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