organic compounds
5-Benzenesulfonamido-2-chlorobenzoic acid
aDepartment of Chemistry, Government College University, Lahore, Pakistan, and bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
In the title compound, C13H10ClNO4S, the dihedral angle between the aromatic ring planes is 87.07 (6)° and an intramolecular C—H⋯O interaction 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
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell 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.
Supporting information
10.1107/S1600536809009787/hb2925sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536809009787/hb2925Isup2.hkl
5-Amino-2-chlorobenzoic acid (1 g, 5.27 mmol) was dissolved in distilled water (10 ml). The pH of the solution was maintained at 8–9 using 1M, Na2CO3 solution. Benzene sulfonyl chloride (0.932 g, 5.27 mmol) was then added to the solution, which was stirred at room temperature until the consumption of all the benzene sulfonyl chloride. During the reaction the pH was again strictly maintained at 8–9 using 1M, Na2CO3. On completion of the reaction the pH was adjusted 1–2, using 1 N HCl under vigorous stirring. The precipitates obtained were filtered off, washed with distilled water and dried. Colourless prisms of (I) were obtained by recrystallization from methanol.
The H-atoms were positioned geometrically, with O-H = 0.82 Å for hydroxy, N—H = 0.86 Å for amine and C—H = 0.93 Å for aromatic H, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C, N, O).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. The dotted lines show the intramolecular H-bonds. | |
Fig. 2. The partial packing diagram of (I) which shows that the molecules are dimerized and linked to each other. |
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 monochromator | 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 |
C13H10ClNO4S | V = 1311.47 (8) Å3 |
Mr = 311.73 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.7139 (4) Å | µ = 0.46 mm−1 |
b = 5.3957 (2) Å | T = 296 K |
c = 20.7565 (8) Å | 0.24 × 0.18 × 0.15 mm |
β = 91.483 (2)° |
Bruker Kappa APEXII CCD diffractometer | 3269 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 2513 reflections with I > 2σ(I) |
Tmin = 0.939, Tmax = 0.940 | Rint = 0.029 |
14693 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.37 e Å−3 |
3269 reflections | Δρmin = −0.36 e Å−3 |
182 parameters |
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 | 1.73 (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) −x, −y+3, −z; (ii) −x, y+1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C13H10ClNO4S |
Mr | 311.73 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 11.7139 (4), 5.3957 (2), 20.7565 (8) |
β (°) | 91.483 (2) |
V (Å3) | 1311.47 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.46 |
Crystal size (mm) | 0.24 × 0.18 × 0.15 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.939, 0.940 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14693, 3269, 2513 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.108, 1.02 |
No. of reflections | 3269 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.36 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
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) |
Symmetry codes: (i) −x, −y+3, −z; (ii) −x, y+1/2, −z+1/2; (iii) x, −y+3/2, z−1/2; (iv) x, y−1, z. |
Acknowledgements
MNA gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a Scholarship under the Indigenous PhD Program (PIN 042–120607-PS2–183).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Sulfonamide derivatives have been used as antibacterial agents. Recently these type of derivatives (Bouchain et al., 2003) have been reported the as antitumor agents. As part of our onging studies of sulfonamide (Arshad, Khan et al., 2009) and thiazine related heterocycles (Arshad et al., 2008), we now report the crystal structure of the title compound, (I), (Fig 1).
The crystal structure of 2-chloro-5-(2-iodobenzenesulfonamido)benzoic acid (Arshad, Tahir et al., 2009), (II), has been reported recently. The title compound differs from (II) as there is no iodoine atom on the phenylsulfonyl moiety. Therefore, (II) is the best structure with which the bond distances etc can be compared. The title compound consists of dimers due to the carboxylic moiety, forming R22(8) ring motifs (Bernstein et al., 1995), (Fig 2). These dimers link each other through the N—H···O type of intermolecular H-bonding where the accepter is the SO2 moiety (Table 1). The benzene rings A (C1—C6) and B (C8—C13) are oriented at a dihedral angle of 87.07 (6)°. The molecules are stabilized due to intra as well as intermolecular H-bonding and the π-interactions (Table 1).