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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o281.
Published online 2009 January 10. doi:  10.1107/S1600536808043869
PMCID: PMC2968399

2-Chloro-5-(2-iodo­benzene­sulfonamido)­benzoic acid

Abstract

In the mol­ecule of the title compound, C13H9ClINO4S, the coordination around the S atom is distorted tetra­hedral. The aromatic rings are oriented at a dihedral angle of 74.46 (9)°. Intra­molecular C—H(...)O hydrogen bonds result in the formation of two five- and one six-membered rings, which adopt planar, envelope and twisted conformations, respectively. In the crystal structure, inter­molecular N—H(...)O and O—H(...)O hydrogen bonds link the mol­ecules to form R 2 2(8) ring motifs, which are further linked by C—H(...)O hydrogen bonds. π–π contacts between the benzene rings [centroid–centroid distances = 3.709 (3) and 3.772 (3) Å] may further stabilize the structure. The I atom is disordered over two positions, refined with occupancies of ca 0.75 and 0.25.

Related literature

For related structures, see: Arshad, Tahir, Khan, Ahmad & Shafiq (2008 [triangle]); Arshad, Tahir, Khan, Shafiq & Siddiqui (2008 [triangle]); Arshad et al. (2009 [triangle]); Deng & Mani (2006 [triangle]). For ring motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o281-scheme1.jpg

Experimental

Crystal data

  • C13H9ClINO4S
  • M r = 437.62
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o281-efi1.jpg
  • a = 26.6375 (9) Å
  • b = 8.5532 (2) Å
  • c = 14.2696 (5) Å
  • β = 111.923 (2)°
  • V = 3016.03 (17) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 2.45 mm−1
  • T = 296 (2) K
  • 0.25 × 0.12 × 0.08 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.708, T max = 0.819
  • 16794 measured reflections
  • 3738 independent reflections
  • 2909 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.069
  • S = 1.05
  • 3738 reflections
  • 203 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.54 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808043869/hk2607sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043869/hk2607Isup2.hkl

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

Acknowledgments

MNA gratefully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Program (PIN 042-120607-PS2-183).

supplementary crystallographic information

Comment

In continuation to our researches with sulfonamides (Arshad, Tahir, Khan, Ahmad & Shafiq, 2008; Arshad, Tahir, Khan, Shafiq & Siddiqui, 2008; Arshad et al., 2009), the title compound has been synthesized, and we report herein its crystal structure.

The structure of the title compound, (I), (Fig 1), differs from 4-[(2-iodo- phenyl)sulfonyl]aminobenzoic acid hydrate, (II) (Arshad et al., 2009), due to the attachment of Cl atom and the change of the position of carboxylate group. Also in (I), there is no water molecule. The coordination around the S atom is a distorted tetrahedral. Rings A(C1-C6) and B(C7-C12) are oriented at a dihedral angle of 74.46 (9)°, which is nearly the same with the corresponding value [74.18 (17)°] in (II). The intramolecular C-H···O hydrogen bonds (Table 1) result in the formations of two five- and one six-membered rings: C (S1/O1/C1/C6/H6), D (O3/C8/C9/C13/H8) and E (S1/O1/N1/C7/C8/H8). Ring C is planar. Ring D adopts envelope conformation with O3 atom displaced by -0.260 (4) Å from the plane of the other rings atoms, while ring E has twisted conformation. The dihedral angle between rings A and C is 2.18 (3)°.

In the crystal structure, intermolecular N-H···O and O-H···O hydrogen bonds (Table 1) link the molecules to form R22(8) ring motifs (Bernstein et al., 1995), they are further linked by C-H···O hydrogen bonds (Table 1, Fig. 2), in which they may be effective in the stabilization of the structure. The π-π contacts between the phenyl rings and the benzene rings, Cg1—Cg1i and Cg2—Cg2ii [symmetry codes: (i) 1/2 - x, 3/2 - y, 1 - z; (ii) -x, 2 - y, -z, where Cg1 and Cg2 are centroids of the rings A (C1-C6) and B(C7-C12), respectively] may further stabilize the structure, with centroid-centroid distances of 3.709 (3) Å and 3.772 (3) Å.

Experimental

The title compound was synthesized according to a literature method (Deng & Mani, 2006). 5-Amino-2-chlorobenzoic acid (0.28 g, 1.66 mmol) was suspended in distilled water (10 ml) in a round bottom flask. The pH of the solution was adjusted to 8-9 using Na2CO3 (1 M). Then, 2-iodobenzene sulfonyl chloride (0.5 g, 1.66 mmol) was added, and stirred at room temperature. The reaction pH was maintained at 8-9. Completion of reaction was indicated by the dissolvation of the suspended 2-iodobenzene sulfonyl chloride. Then, pH was adjusted to 2-3 using HCl (2 N). The precipitate formed was filtered, washed with distilled water, and then recrystalyzed in methanol.

Refinement

The iodine atom was disordered over two positions. During the refinement process the disordered atoms I1A and I1B were refined with occupancies of 0.75 and 0.25, respectively. H3O (for OH) atom was located in difference syntheses and refined [O-H = 0.76 (4) Å, Uiso(H) = 1.2Ueq(O)]. The remaining H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93 Å for aromatic H, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
Fig. 2.
A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C13H9ClINO4SF(000) = 1696
Mr = 437.62Dx = 1.928 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3738 reflections
a = 26.6375 (9) Åθ = 2.5–28.3°
b = 8.5532 (2) ŵ = 2.45 mm1
c = 14.2696 (5) ÅT = 296 K
β = 111.923 (2)°Needle, light brown
V = 3016.03 (17) Å30.25 × 0.12 × 0.08 mm
Z = 8

Data collection

Bruker Kappa APEXII CCD diffractometer3738 independent reflections
Radiation source: fine-focus sealed tube2909 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 7.40 pixels mm-1θmax = 28.3°, θmin = 2.5°
ω scansh = −34→35
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −11→11
Tmin = 0.708, Tmax = 0.819l = −18→18
16794 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0301P)2 + 3.5121P] where P = (Fo2 + 2Fc2)/3
3738 reflections(Δ/σ)max = 0.002
203 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = −0.31 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
I1A0.12215 (4)0.55411 (16)0.41289 (12)0.0562 (2)0.750
I1B0.12364 (17)0.5371 (5)0.4021 (4)0.0789 (10)0.250
Cl1−0.04930 (3)1.21242 (9)0.10878 (7)0.0669 (3)
S10.16694 (2)0.68574 (6)0.21704 (5)0.0391 (2)
O10.18866 (8)0.7712 (2)0.15530 (16)0.0565 (7)
O20.18272 (7)0.52454 (19)0.23828 (15)0.0482 (6)
O30.13053 (10)1.2455 (2)0.1957 (2)0.0776 (9)
O40.05294 (9)1.3743 (2)0.13943 (18)0.0690 (8)
N10.10171 (8)0.6828 (2)0.16552 (17)0.0441 (7)
C10.18390 (9)0.7924 (3)0.33142 (18)0.0361 (7)
C20.16797 (10)0.7500 (3)0.4100 (2)0.0418 (8)
C30.18262 (12)0.8446 (4)0.4949 (2)0.0556 (10)
C40.21208 (13)0.9786 (4)0.5010 (3)0.0624 (11)
C50.22800 (12)1.0202 (3)0.4236 (3)0.0578 (10)
C60.21433 (10)0.9275 (3)0.3391 (2)0.0453 (8)
C70.06742 (10)0.8137 (2)0.15009 (18)0.0371 (7)
C80.08656 (10)0.9658 (2)0.15617 (19)0.0402 (7)
C90.05220 (10)1.0940 (3)0.14506 (18)0.0394 (7)
C10−0.00221 (11)1.0655 (3)0.12406 (19)0.0436 (8)
C11−0.02139 (11)0.9137 (3)0.1157 (2)0.0490 (8)
C120.01314 (10)0.7883 (3)0.1292 (2)0.0451 (8)
C130.07726 (12)1.2528 (3)0.1587 (2)0.0456 (8)
H10.086560.593520.145790.0529*
H30.172390.817000.548290.0667*
H3O0.1464 (16)1.322 (5)0.207 (3)0.0931*
H40.221301.041510.558110.0749*
H50.248001.111020.428210.0695*
H60.225450.955030.286810.0544*
H80.122890.982810.167840.0482*
H11−0.058020.896060.100690.0588*
H12−0.000120.686810.124270.0541*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I1A0.0535 (3)0.0462 (3)0.0796 (5)−0.0084 (2)0.0373 (3)0.0109 (4)
I1B0.106 (2)0.0709 (18)0.0809 (13)−0.0395 (13)0.0591 (12)−0.0108 (9)
Cl10.0705 (5)0.0508 (4)0.0822 (5)0.0268 (3)0.0318 (4)0.0054 (4)
S10.0453 (3)0.0250 (3)0.0528 (4)0.0010 (2)0.0250 (3)−0.0009 (2)
O10.0748 (13)0.0452 (10)0.0659 (13)−0.0060 (9)0.0452 (11)−0.0017 (9)
O20.0482 (10)0.0272 (8)0.0719 (13)0.0059 (7)0.0255 (9)−0.0022 (8)
O30.0640 (15)0.0245 (9)0.140 (2)−0.0043 (9)0.0331 (15)−0.0062 (11)
O40.0735 (14)0.0240 (9)0.0982 (17)0.0068 (9)0.0190 (12)0.0050 (9)
N10.0451 (11)0.0202 (8)0.0602 (14)0.0000 (8)0.0119 (10)−0.0022 (8)
C10.0333 (11)0.0271 (10)0.0489 (14)0.0007 (8)0.0166 (10)0.0000 (9)
C20.0379 (13)0.0389 (12)0.0531 (15)0.0018 (10)0.0221 (11)0.0042 (11)
C30.0577 (17)0.0623 (18)0.0538 (17)0.0023 (14)0.0290 (14)−0.0012 (13)
C40.0660 (19)0.0542 (17)0.0633 (19)−0.0021 (14)0.0198 (16)−0.0204 (14)
C50.0598 (18)0.0364 (14)0.073 (2)−0.0110 (12)0.0200 (16)−0.0077 (13)
C60.0444 (14)0.0344 (12)0.0583 (16)−0.0061 (10)0.0205 (12)0.0012 (11)
C70.0459 (13)0.0241 (10)0.0378 (12)0.0028 (9)0.0115 (10)0.0001 (9)
C80.0458 (13)0.0255 (10)0.0476 (14)0.0015 (9)0.0155 (11)0.0015 (9)
C90.0551 (15)0.0246 (10)0.0376 (13)0.0035 (9)0.0163 (11)0.0014 (9)
C100.0545 (15)0.0362 (12)0.0398 (13)0.0129 (10)0.0172 (11)0.0012 (10)
C110.0456 (14)0.0440 (14)0.0541 (16)0.0017 (11)0.0147 (12)−0.0001 (12)
C120.0465 (14)0.0310 (11)0.0539 (15)−0.0024 (10)0.0143 (12)0.0006 (10)
C130.0632 (17)0.0253 (11)0.0490 (15)0.0040 (10)0.0218 (13)0.0007 (10)

Geometric parameters (Å, °)

I1A—C22.082 (3)C4—C51.370 (5)
I1B—C22.150 (5)C5—C61.374 (4)
Cl1—C101.731 (3)C7—C121.380 (4)
S1—O11.423 (2)C7—C81.388 (3)
S1—O21.4403 (17)C8—C91.399 (3)
S1—N11.614 (2)C9—C101.388 (4)
S1—C11.775 (3)C9—C131.494 (4)
O3—C131.318 (4)C10—C111.384 (4)
O4—C131.201 (3)C11—C121.379 (4)
O3—H3O0.76 (4)C3—H30.9300
N1—C71.409 (3)C4—H40.9300
N1—H10.8600C5—H50.9300
C1—C61.392 (4)C6—H60.9300
C1—C21.387 (4)C8—H80.9300
C2—C31.386 (4)C11—H110.9300
C3—C41.373 (5)C12—H120.9300
I1A···O23.446 (2)C1···C83.215 (3)
I1A···N13.540 (3)C2···C4ii3.552 (5)
I1A···Cl1i3.4575 (16)C4···C2ii3.552 (5)
I1A···C5ii3.851 (4)C4···O1x3.293 (4)
I1B···O23.271 (6)C5···I1Aii3.851 (4)
I1B···N13.438 (6)C5···I1Bii3.835 (6)
I1B···C5ii3.835 (6)C6···C83.445 (4)
I1B···Cl1i3.381 (5)C6···O2xi3.419 (3)
I1A···H12iii3.2900C7···Cl1v3.549 (3)
I1A···H11iii3.3600C8···O13.193 (3)
Cl1···O42.939 (3)C8···C63.445 (4)
Cl1···I1Aiv3.4575 (16)C8···C13.215 (3)
Cl1···I1Biv3.381 (5)C9···C11v3.499 (4)
Cl1···C7v3.549 (3)C10···C10iii3.552 (4)
S1···H3Ovi3.15 (4)C11···C11iii3.568 (4)
S1···H82.7800C11···C9v3.499 (4)
O1···C83.193 (3)C1···H82.8100
O1···C4vii3.293 (4)C6···H82.7700
O2···O3vi2.714 (3)C13···H1ix2.9400
O2···I1B3.271 (6)H1···O4vi2.0700
O2···I1A3.446 (2)H1···C13vi2.9400
O2···C6viii3.419 (3)H1···H122.3500
O3···O2ix2.714 (3)H3···O3x2.7800
O4···N1ix2.903 (3)H3O···S1ix3.15 (4)
O4···Cl12.939 (3)H3O···O2ix1.95 (4)
O1···H82.5700H4···O1x2.4800
O1···H4vii2.4800H5···O1xi2.7600
O1···H62.3600H6···O12.3600
O1···H5viii2.7600H6···O2xi2.6700
O2···H6viii2.6700H8···S12.7800
O2···H3Ovi1.95 (4)H8···O12.5700
O3···H3vii2.7800H8···O32.2800
O3···H82.2800H8···C12.8100
O4···H1ix2.0700H8···C62.7700
N1···I1A3.540 (3)H11···I1Aiii3.3600
N1···I1B3.438 (6)H12···H12.3500
N1···O4vi2.903 (3)H12···I1Aiii3.2900
O1—S1—O2117.89 (12)C8—C9—C10118.2 (2)
O1—S1—N1110.08 (12)C8—C9—C13117.2 (2)
O1—S1—C1106.41 (12)C10—C9—C13124.6 (2)
O2—S1—N1105.12 (11)Cl1—C10—C9123.3 (2)
O2—S1—C1110.15 (12)Cl1—C10—C11116.3 (2)
N1—S1—C1106.73 (12)C9—C10—C11120.4 (3)
C13—O3—H3O118 (3)C10—C11—C12120.8 (3)
S1—N1—C7125.69 (16)C7—C12—C11119.9 (2)
C7—N1—H1117.00O3—C13—O4122.7 (3)
S1—N1—H1117.00O3—C13—C9111.8 (2)
S1—C1—C6116.10 (19)O4—C13—C9125.5 (3)
S1—C1—C2124.0 (2)C2—C3—H3120.00
C2—C1—C6119.9 (2)C4—C3—H3120.00
I1A—C2—C1125.8 (2)C3—C4—H4120.00
I1A—C2—C3115.4 (2)C5—C4—H4120.00
C1—C2—C3118.9 (3)C4—C5—H5120.00
I1B—C2—C1120.5 (2)C6—C5—H5120.00
I1B—C2—C3120.7 (3)C1—C6—H6120.00
C2—C3—C4120.7 (3)C5—C6—H6120.00
C3—C4—C5120.5 (3)C7—C8—H8119.00
C4—C5—C6119.8 (3)C9—C8—H8119.00
C1—C6—C5120.3 (3)C10—C11—H11120.00
C8—C7—C12119.5 (2)C12—C11—H11120.00
N1—C7—C8122.2 (2)C7—C12—H12120.00
N1—C7—C12118.31 (19)C11—C12—H12120.00
C7—C8—C9121.2 (3)
O1—S1—N1—C7−65.6 (2)C3—C4—C5—C60.1 (5)
O2—S1—N1—C7166.5 (2)C4—C5—C6—C10.7 (5)
C1—S1—N1—C749.5 (2)N1—C7—C8—C9−177.1 (2)
O1—S1—C1—C2177.4 (2)C12—C7—C8—C92.3 (4)
O1—S1—C1—C6−1.6 (2)N1—C7—C12—C11178.7 (2)
O2—S1—C1—C2−53.8 (3)C8—C7—C12—C11−0.7 (4)
O2—S1—C1—C6127.3 (2)C7—C8—C9—C10−2.3 (4)
N1—S1—C1—C259.8 (3)C7—C8—C9—C13176.6 (2)
N1—S1—C1—C6−119.1 (2)C8—C9—C10—Cl1179.79 (19)
S1—N1—C7—C815.6 (4)C8—C9—C10—C110.8 (4)
S1—N1—C7—C12−163.8 (2)C13—C9—C10—Cl11.0 (4)
S1—C1—C2—I1A0.7 (4)C13—C9—C10—C11−178.1 (2)
S1—C1—C2—C3−178.5 (2)C8—C9—C13—O3−10.3 (3)
C6—C1—C2—I1A179.6 (2)C8—C9—C13—O4170.0 (3)
C6—C1—C2—C30.4 (4)C10—C9—C13—O3168.5 (3)
S1—C1—C6—C5178.0 (2)C10—C9—C13—O4−11.2 (4)
C2—C1—C6—C5−0.9 (4)Cl1—C10—C11—C12−178.3 (2)
I1A—C2—C3—C4−178.9 (3)C9—C10—C11—C120.8 (4)
C1—C2—C3—C40.4 (5)C10—C11—C12—C7−0.8 (4)
C2—C3—C4—C5−0.7 (5)

Symmetry codes: (i) −x, y−1, −z+1/2; (ii) −x+1/2, −y+3/2, −z+1; (iii) −x, y, −z+1/2; (iv) −x, y+1, −z+1/2; (v) −x, −y+2, −z; (vi) x, y−1, z; (vii) x, −y+2, z−1/2; (viii) −x+1/2, y−1/2, −z+1/2; (ix) x, y+1, z; (x) x, −y+2, z+1/2; (xi) −x+1/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O4vi0.862.072.903 (3)164
O3—H3O···O2ix0.76 (4)1.95 (4)2.714 (3)176 (5)
C4—H4···O1x0.932.483.293 (4)146
C6—H6···O10.932.362.792 (3)108
C8—H8···O10.932.573.193 (3)125
C8—H8···O30.932.282.631 (3)102

Symmetry codes: (vi) x, y−1, z; (ix) x, y+1, z; (x) x, −y+2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2607).

References

  • Arshad, M. N., Tahir, M. N., Khan, I. U., Ahmad, E. & Shafiq, M. (2008). Acta Cryst. E64, o2380. [PMC free article] [PubMed]
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