5-Benzene-sulfonamido-2-chloro-benzoic acid.

In the title compound, C(13)H(10)ClNO(4)S, the dihedral angle between the aromatic ring planes is 87.07 (6)° and an intra-molecular C-H⋯O inter-action occurs. In the crystal, inversion dimers linked by two O-H⋯O hydrogen bonds arise from the carboxyl groups. N-H⋯O hydrogen bonds link the dimers into chains and short C-Cl⋯π and S-O⋯π contacts are also seen.

Related literature

For related structures: see: Arshad et al. (2008 ▶); Arshad, Khan et al. (2009 ▶); Arshad, Tahir et al. (2009 ▶). For chemical background, see: Bouchain et al. (2003 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H10ClNO4S

M = 311.73

Monoclinic,

a = 11.7139 (4) Å

b = 5.3957 (2) Å

c = 20.7565 (8) Å

β = 91.483 (2)°

V = 1311.47 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 296 K

0.24 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.939, T max = 0.940

14693 measured reflections

3269 independent reflections

2513 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.02

3269 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.36 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, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009787/hb2925sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009787/hb2925Isup2.hkl

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

C13H10ClNO4S	F(000) = 640
Mr = 311.73	Dx = 1.579 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2234 reflections
a = 11.7139 (4) Å	θ = 2.1–27.0°
b = 5.3957 (2) Å	µ = 0.46 mm−1
c = 20.7565 (8) Å	T = 296 K
β = 91.483 (2)°	Prismatic, colorless
V = 1311.47 (8) Å3	0.24 × 0.18 × 0.15 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3269 independent reflections
Radiation source: fine-focus sealed tube	2513 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 2.6°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→7
Tmin = 0.939, Tmax = 0.940	l = −27→27
14693 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.048P)2 + 0.7097P] where P = (Fo2 + 2Fc2)/3
3269 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.36 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 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
Cl1	0.34738 (5)	1.16021 (13)	−0.01036 (3)	0.0671 (2)
S1	0.18337 (4)	0.37106 (8)	0.24025 (2)	0.0317 (1)
O1	−0.00951 (12)	1.2492 (3)	0.05816 (8)	0.0530 (5)
O2	0.12244 (13)	1.3665 (3)	−0.00925 (8)	0.0557 (5)
O3	0.08966 (12)	0.2790 (3)	0.27620 (7)	0.0460 (5)
O4	0.25750 (12)	0.2023 (3)	0.20902 (7)	0.0420 (4)
N1	0.12278 (13)	0.5510 (3)	0.18667 (8)	0.0370 (5)
C1	0.16292 (15)	1.0292 (3)	0.06222 (9)	0.0320 (5)
C2	0.11598 (15)	0.8798 (3)	0.10932 (9)	0.0311 (5)
C3	0.17784 (15)	0.6911 (3)	0.13923 (9)	0.0313 (5)
C4	0.28911 (17)	0.6482 (4)	0.12081 (10)	0.0420 (6)
C5	0.33651 (18)	0.7953 (4)	0.07447 (11)	0.0465 (7)
C6	0.27543 (17)	0.9845 (4)	0.04525 (10)	0.0385 (6)
C7	0.09147 (16)	1.2312 (4)	0.03343 (9)	0.0344 (6)
C8	0.26803 (15)	0.5589 (3)	0.29150 (9)	0.0322 (5)
C9	0.21566 (19)	0.7353 (4)	0.32856 (11)	0.0484 (7)
C10	0.2813 (2)	0.8817 (5)	0.36915 (13)	0.0645 (9)
C11	0.3978 (2)	0.8482 (5)	0.37292 (13)	0.0655 (10)
C12	0.4499 (2)	0.6723 (5)	0.33606 (12)	0.0558 (8)
C13	0.38461 (17)	0.5253 (4)	0.29468 (10)	0.0432 (7)
H1N	0.04957	0.56188	0.18730	0.0444*
H1O	−0.04283	1.36994	0.04279	0.0636*
H2	0.04096	0.90730	0.12110	0.0374*
H4	0.33146	0.52045	0.13970	0.0503*
H5	0.41138	0.76657	0.06261	0.0558*
H9	0.13680	0.75516	0.32615	0.0580*
H10	0.24711	1.00298	0.39397	0.0773*
H11	0.44182	0.94605	0.40084	0.0786*
H12	0.52867	0.65190	0.33884	0.0670*
H13	0.41898	0.40565	0.26941	0.0519*

	U11	U22	U33	U12	U13	U23
Cl1	0.0512 (3)	0.0760 (4)	0.0756 (4)	0.0223 (3)	0.0284 (3)	0.0383 (3)
S1	0.0291 (2)	0.0308 (2)	0.0350 (3)	−0.0010 (2)	0.0002 (2)	0.0017 (2)
O1	0.0393 (8)	0.0620 (10)	0.0582 (10)	0.0216 (7)	0.0088 (7)	0.0238 (8)
O2	0.0443 (8)	0.0601 (10)	0.0631 (10)	0.0182 (7)	0.0114 (7)	0.0283 (8)
O3	0.0363 (7)	0.0478 (8)	0.0540 (9)	−0.0098 (6)	0.0038 (6)	0.0115 (7)
O4	0.0442 (8)	0.0354 (7)	0.0462 (8)	0.0065 (6)	−0.0018 (6)	−0.0055 (6)
N1	0.0261 (8)	0.0457 (9)	0.0392 (9)	0.0047 (7)	−0.0004 (6)	0.0085 (7)
C1	0.0325 (9)	0.0349 (9)	0.0284 (9)	0.0056 (7)	−0.0025 (7)	−0.0021 (7)
C2	0.0264 (8)	0.0373 (9)	0.0295 (9)	0.0046 (7)	−0.0020 (7)	−0.0035 (8)
C3	0.0306 (9)	0.0342 (9)	0.0291 (9)	0.0030 (7)	−0.0014 (7)	−0.0019 (7)
C4	0.0353 (10)	0.0448 (11)	0.0460 (12)	0.0138 (9)	0.0047 (8)	0.0102 (9)
C5	0.0342 (10)	0.0539 (13)	0.0519 (13)	0.0159 (9)	0.0114 (9)	0.0118 (10)
C6	0.0356 (10)	0.0430 (11)	0.0372 (10)	0.0060 (8)	0.0059 (8)	0.0050 (9)
C7	0.0322 (9)	0.0382 (10)	0.0326 (10)	0.0053 (8)	−0.0027 (7)	−0.0012 (8)
C8	0.0333 (9)	0.0335 (9)	0.0297 (9)	−0.0038 (7)	0.0016 (7)	0.0022 (7)
C9	0.0438 (12)	0.0503 (12)	0.0512 (13)	0.0002 (10)	0.0056 (10)	−0.0115 (10)
C10	0.0680 (17)	0.0646 (16)	0.0611 (16)	−0.0072 (13)	0.0067 (13)	−0.0284 (13)
C11	0.0665 (17)	0.0720 (18)	0.0577 (15)	−0.0258 (14)	−0.0038 (13)	−0.0170 (13)
C12	0.0362 (11)	0.0722 (16)	0.0587 (14)	−0.0131 (11)	−0.0050 (10)	−0.0017 (12)
C13	0.0351 (10)	0.0513 (12)	0.0433 (12)	−0.0005 (9)	0.0032 (8)	−0.0024 (10)

Cl1—C6	1.730 (2)	C5—C6	1.378 (3)
S1—O3	1.4321 (15)	C8—C13	1.378 (3)
S1—O4	1.4257 (16)	C8—C9	1.378 (3)
S1—N1	1.6255 (17)	C9—C10	1.375 (3)
S1—C8	1.7572 (18)	C10—C11	1.377 (3)
O1—C7	1.305 (2)	C11—C12	1.372 (4)
O2—C7	1.211 (3)	C12—C13	1.385 (3)
O1—H1O	0.8200	C2—H2	0.9300
N1—C3	1.411 (2)	C4—H4	0.9300
N1—H1N	0.8600	C5—H5	0.9300
C1—C6	1.394 (3)	C9—H9	0.9300
C1—C7	1.490 (3)	C10—H10	0.9300
C1—C2	1.391 (3)	C11—H11	0.9300
C2—C3	1.387 (2)	C12—H12	0.9300
C3—C4	1.387 (3)	C13—H13	0.9300
C4—C5	1.375 (3)
O3—S1—O4	119.97 (9)	S1—C8—C9	118.95 (15)
O3—S1—N1	103.69 (9)	S1—C8—C13	119.76 (14)
O3—S1—C8	108.23 (9)	C9—C8—C13	121.29 (18)
O4—S1—N1	109.31 (9)	C8—C9—C10	119.3 (2)
O4—S1—C8	107.63 (9)	C9—C10—C11	119.8 (2)
N1—S1—C8	107.41 (8)	C10—C11—C12	120.9 (2)
C7—O1—H1O	109.00	C11—C12—C13	119.7 (2)
S1—N1—C3	126.74 (13)	C8—C13—C12	119.03 (19)
C3—N1—H1N	117.00	C1—C2—H2	119.00
S1—N1—H1N	117.00	C3—C2—H2	119.00
C2—C1—C6	118.08 (16)	C3—C4—H4	120.00
C2—C1—C7	118.53 (16)	C5—C4—H4	120.00
C6—C1—C7	123.38 (17)	C4—C5—H5	119.00
C1—C2—C3	121.90 (16)	C6—C5—H5	119.00
N1—C3—C2	117.57 (16)	C8—C9—H9	120.00
N1—C3—C4	123.56 (16)	C10—C9—H9	120.00
C2—C3—C4	118.87 (17)	C9—C10—H10	120.00
C3—C4—C5	119.72 (19)	C11—C10—H10	120.00
C4—C5—C6	121.4 (2)	C10—C11—H11	120.00
C1—C6—C5	120.03 (19)	C12—C11—H11	120.00
Cl1—C6—C5	116.31 (16)	C11—C12—H12	120.00
Cl1—C6—C1	123.64 (16)	C13—C12—H12	120.00
O1—C7—O2	122.32 (19)	C8—C13—H13	120.00
O1—C7—C1	113.71 (17)	C12—C13—H13	120.00
O2—C7—C1	123.97 (17)
O3—S1—N1—C3	179.16 (16)	C2—C1—C7—O2	−177.51 (19)
O4—S1—N1—C3	−51.79 (18)	C6—C1—C7—O1	−176.84 (18)
C8—S1—N1—C3	64.71 (17)	C6—C1—C7—O2	3.7 (3)
O3—S1—C8—C9	−47.55 (18)	C1—C2—C3—N1	179.62 (16)
O3—S1—C8—C13	131.51 (16)	C1—C2—C3—C4	−1.0 (3)
O4—S1—C8—C9	−178.57 (16)	N1—C3—C4—C5	−179.45 (19)
O4—S1—C8—C13	0.48 (18)	C2—C3—C4—C5	1.2 (3)
N1—S1—C8—C9	63.83 (18)	C3—C4—C5—C6	−0.6 (3)
N1—S1—C8—C13	−117.12 (16)	C4—C5—C6—Cl1	178.09 (17)
S1—N1—C3—C2	−163.64 (14)	C4—C5—C6—C1	−0.4 (3)
S1—N1—C3—C4	17.0 (3)	S1—C8—C9—C10	179.51 (18)
C6—C1—C2—C3	0.1 (3)	C13—C8—C9—C10	0.5 (3)
C7—C1—C2—C3	−178.76 (17)	S1—C8—C13—C12	−179.00 (17)
C2—C1—C6—Cl1	−177.75 (15)	C9—C8—C13—C12	0.0 (3)
C2—C1—C6—C5	0.6 (3)	C8—C9—C10—C11	−0.9 (4)
C7—C1—C6—Cl1	1.1 (3)	C9—C10—C11—C12	0.8 (4)
C7—C1—C6—C5	179.40 (19)	C10—C11—C12—C13	−0.3 (4)
C2—C1—C7—O1	2.0 (3)	C11—C12—C13—C8	−0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2i	0.82	1.83	2.648 (2)	178
N1—H1N···O3ii	0.86	2.16	2.898 (2)	144
C4—H4···O4	0.93	2.41	3.052 (3)	126
C6—Cl1···CgBiii	1.730 (2)	3.8131 (12)	4.605 (2)	106.16 (8)
S1—O4···CgAiv	1.4257 (16)	3.1405 (17)	4.2532 (9)	133.77 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O2i	0.82	1.83	2.648 (2)	178
N1—H1N⋯O3ii	0.86	2.16	2.898 (2)	144
C4—H4⋯O4	0.93	2.41	3.052 (3)	126
C6—Cl1⋯CgBiii	1.73 (1)	3.81 (1)	4.605 (2)	106 (1)
S1—O4⋯CgAiv	1.43 (1)	3.14 (1)	4.2532 (9)	134 (1)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . CgA and CgB are the centroids of the C1–C6 and C8–C13 benzene rings, respectively.