Skip to main content
NCBI home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 May 7;67(Pt 6):o1327. doi: 10.1107/S1600536811016412

2-Chloro-4-(2-iodo­benzene­sulfonamido)­benzoic acid

Muhammad Nadeem Arshad a,*,‡, Islam Ullah Khan b, H M Rafique a, Abdullah M Asiri c, Muhammad Shafiq b
PMCID: PMC3120592  PMID: 21754724

Abstract

In the title compound, C13H9ClINO4S, the dihedral angle between the aromatic rings is 81.04 (17)°. The disposition of the I and Cl atoms attached to the two rings is anti. In the crystal, mol­ecules are connected via O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For background to thia­zine heterocycles, see: Arshad et al. (2008, ▶ 2011 ▶). For their biological activity, see: Medina et al. (1999 ▶). For related structures, see: Arshad et al. (2009a ▶,b ▶,c ▶).graphic file with name e-67-o1327-scheme1.jpg

Experimental

Crystal data

  • C13H9ClINO4S

  • M r = 437.62

  • Monoclinic, Inline graphic

  • a = 14.1522 (8) Å

  • b = 7.3203 (4) Å

  • c = 14.7193 (8) Å

  • β = 104.892 (2)°

  • V = 1473.68 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.51 mm−1

  • T = 296 K

  • 0.18 × 0.15 × 0.09 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.661, T max = 0.806

  • 16645 measured reflections

  • 3668 independent reflections

  • 1876 reflections with I > 2σ(I)

  • R int = 0.058

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054

  • wR(F 2) = 0.129

  • S = 1.03

  • 3668 reflections

  • 191 parameters

  • H-atom parameters constrained

  • Δρmax = 1.24 e Å−3

  • Δρmin = −1.30 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 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016412/hb5865sup1.cif

e-67-o1327-sup1.cif (17.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016412/hb5865Isup2.hkl

e-67-o1327-Isup2.hkl (176.2KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811016412/hb5865Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O2i 0.86 2.38 3.214 (6) 162
O1—H1O⋯O2ii 0.82 2.09 2.771 (6) 140
Open in a new tab

Symmetry codes: (i) Inline graphic; (ii) Inline graphic.

Acknowledgments

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant for the project to strengthen the Materials Chemistry Laboratory at GC University, Lahore, Pakistan.

supplementary crystallographic information

Comment

The title compound, (I), is an example of a halogenated sulfonamide, which are reported as inhibitors for the growth of multidrug resistant MCF-7/ADR cancer cells (Medina et al., 1999). In continuation to our researches with sulfonamides (Arshad et al., 2009a), the title compound has been prepared, as an intermediate for the preparation of thiazine related heterocycles (Arshad et al., 2008, 2011).

The crystal structure of (I) being reported here as an isomer of previously reported compound 2-chloro-5-(2-iodobenzenesulfonamido)benzoic acid (II), (Arshad, et al., 2009a). The bond lengths and bond angles are also compareable with the 5-benzenesulfonamido-2-chlorobenzoic acid (III), (Arshad, et al., 2009b) and 4-(2-Iodobenzenesulfonamido)benzoic acid monohydrate (IV) (Arshad, et al., 2009c). The two aromatic rings A (C1-C6) and B (C7-C12) are oriented at dihedral angle of 81.04 (17)° which is lower than in (IV i.e. 87.07 (6)°) and greater than in (II i.e. 74.46 (9)°) and (III i.e. 74.18 (17)°). No intramolecular hydrogen bonding interaction have been observed in the molecule. The intermolecular interaction of O—H···O and N—H···O forms three dimentional network to stabilize structure of molecule (Fig. 2 and Tab. 1).

Experimental

The title compound was prepared following the method of Arshad et al. (2009a). Red needles were recrystallised from methanol.

Refinement

All the H-atoms were positioned with idealized geometry with C—H = 0.93 Å, N—H = 0.86 Å, O—H = 0.82 Å and were refined using a riding model with Uiso(H) = 1.2 Ueqfor aromatic C and N atoms and with Uiso(H) = 1.5 Ueqfor O atom.

Figures

Fig. 1.

Fig. 1.

Open in a new tab

The structure of (I) with displacement ellipsoids drawn at the 50% probability level.

Fig. 2.

Fig. 2.

Open in a new tab

Unit cell packing for (I) with hydrogen bonding shown as dashed lines.

Crystal data

C13H9ClINO4S F(000) = 848
Mr = 437.62 Dx = 1.972 Mg m−3
Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 2692 reflections
a = 14.1522 (8) Å θ = 2.9–22.2°
b = 7.3203 (4) Å µ = 2.51 mm−1
c = 14.7193 (8) Å T = 296 K
β = 104.892 (2)° Needle, red
V = 1473.68 (14) Å3 0.18 × 0.15 × 0.09 mm
Z = 4
Open in a new tab

Data collection

Bruker Kappa APEXII CCD diffractometer 3668 independent reflections
Radiation source: fine-focus sealed tube 1876 reflections with I > 2σ(I)
graphite Rint = 0.058
φ and ω scans θmax = 28.3°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007) h = −18→18
Tmin = 0.661, Tmax = 0.806 k = −9→5
16645 measured reflections l = −19→18
Open in a new tab

Refinement

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)] = 0.054 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129 H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0383P)2 + 3.6338P] where P = (Fo2 + 2Fc2)/3
3668 reflections (Δ/σ)max < 0.001
191 parameters Δρmax = 1.24 e Å−3
0 restraints Δρmin = −1.30 e Å−3
Open in a new tab

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.
Open in a new tab

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

x y z Uiso*/Ueq
I1 0.09820 (4) 0.29186 (7) −0.02615 (4) 0.0813 (2)
Cl1 0.57812 (11) −0.0907 (2) 0.24047 (12) 0.0606 (5)
S1 0.22376 (11) −0.1302 (2) −0.02876 (11) 0.0446 (4)
O2 0.6990 (3) 0.2380 (5) 0.2686 (3) 0.0522 (11)
O3 0.1453 (3) −0.1280 (6) −0.1113 (3) 0.0608 (12)
O4 0.2813 (3) −0.2894 (6) −0.0053 (4) 0.0685 (13)
O1 0.6486 (3) 0.4890 (5) 0.1868 (3) 0.0587 (12)
H1O 0.6958 0.5337 0.2247 0.088*
N1 0.2946 (3) 0.0364 (6) −0.0429 (3) 0.0415 (12)
H1 0.2808 0.0897 −0.0967 0.050*
C1 0.1801 (4) −0.0725 (8) 0.0698 (4) 0.0443 (14)
C2 0.1285 (4) 0.0854 (10) 0.0765 (5) 0.0549 (17)
C3 0.0945 (5) 0.1169 (14) 0.1543 (6) 0.082 (3)
H3 0.0604 0.2237 0.1588 0.099*
C4 0.1104 (8) −0.005 (2) 0.2231 (8) 0.116 (4)
H4 0.0860 0.0174 0.2749 0.140*
C5 0.1625 (7) −0.1670 (17) 0.2205 (6) 0.102 (4)
H5 0.1740 −0.2503 0.2698 0.122*
C6 0.1957 (5) −0.1974 (11) 0.1423 (6) 0.070 (2)
H6 0.2295 −0.3047 0.1380 0.085*
C7 0.3765 (4) 0.1009 (7) 0.0255 (4) 0.0315 (12)
C8 0.4328 (4) −0.0092 (7) 0.0936 (4) 0.0372 (13)
H8 0.4155 −0.1309 0.0976 0.045*
C9 0.5151 (4) 0.0594 (7) 0.1565 (4) 0.0350 (13)
C10 0.5457 (4) 0.2393 (6) 0.1501 (4) 0.0297 (11)
C11 0.4845 (4) 0.3480 (7) 0.0827 (4) 0.0390 (13)
H11 0.5006 0.4704 0.0788 0.047*
C12 0.4019 (4) 0.2832 (7) 0.0222 (4) 0.0384 (13)
H12 0.3625 0.3611 −0.0214 0.046*
C13 0.6385 (4) 0.3173 (7) 0.2090 (4) 0.0364 (13)
Open in a new tab

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
I1 0.0650 (3) 0.0593 (3) 0.1146 (5) 0.0148 (2) 0.0143 (3) −0.0042 (3)
Cl1 0.0512 (9) 0.0458 (8) 0.0741 (12) 0.0036 (7) −0.0037 (8) 0.0291 (8)
S1 0.0403 (8) 0.0417 (8) 0.0510 (10) −0.0072 (6) 0.0103 (8) −0.0130 (7)
O2 0.038 (2) 0.048 (2) 0.059 (3) 0.0023 (18) −0.010 (2) 0.007 (2)
O3 0.055 (3) 0.071 (3) 0.051 (3) −0.018 (2) 0.003 (2) −0.023 (2)
O4 0.060 (3) 0.039 (2) 0.105 (4) −0.004 (2) 0.020 (3) −0.013 (2)
O1 0.069 (3) 0.044 (2) 0.045 (3) −0.019 (2) −0.017 (2) 0.006 (2)
N1 0.037 (3) 0.058 (3) 0.027 (3) −0.008 (2) 0.005 (2) 0.001 (2)
C1 0.034 (3) 0.057 (4) 0.041 (4) −0.013 (3) 0.006 (3) 0.001 (3)
C2 0.034 (3) 0.077 (5) 0.053 (4) −0.020 (3) 0.010 (3) −0.020 (4)
C3 0.062 (5) 0.125 (7) 0.075 (6) −0.020 (5) 0.045 (5) −0.039 (6)
C4 0.091 (8) 0.201 (13) 0.070 (7) −0.062 (8) 0.045 (6) −0.020 (8)
C5 0.082 (7) 0.160 (10) 0.057 (6) −0.047 (7) 0.009 (5) 0.040 (7)
C6 0.053 (4) 0.085 (5) 0.070 (5) −0.016 (4) 0.009 (4) 0.016 (4)
C7 0.030 (3) 0.041 (3) 0.026 (3) −0.002 (2) 0.013 (2) −0.001 (2)
C8 0.037 (3) 0.035 (3) 0.042 (4) 0.000 (2) 0.013 (3) 0.003 (3)
C9 0.036 (3) 0.036 (3) 0.034 (3) 0.010 (2) 0.012 (3) 0.011 (2)
C10 0.029 (3) 0.031 (3) 0.031 (3) 0.002 (2) 0.011 (2) 0.000 (2)
C11 0.042 (3) 0.037 (3) 0.036 (3) −0.002 (2) 0.006 (3) 0.005 (2)
C12 0.036 (3) 0.040 (3) 0.036 (3) 0.000 (2) 0.002 (3) 0.012 (3)
C13 0.041 (3) 0.038 (3) 0.031 (3) −0.001 (2) 0.012 (3) 0.001 (2)
Open in a new tab

Geometric parameters (Å, °)

I1—C2 2.102 (7) C4—C5 1.401 (14)
Cl1—C9 1.722 (5) C4—H4 0.9300
S1—O4 1.413 (4) C5—C6 1.368 (12)
S1—O3 1.420 (4) C5—H5 0.9300
S1—N1 1.626 (5) C6—H6 0.9300
S1—C1 1.767 (6) C7—C8 1.371 (7)
O2—C13 1.206 (6) C7—C12 1.386 (7)
O1—C13 1.315 (6) C8—C9 1.383 (7)
O1—H1O 0.8200 C8—H8 0.9300
N1—C7 1.407 (6) C9—C10 1.396 (7)
N1—H1 0.8600 C10—C11 1.388 (7)
C1—C6 1.380 (9) C10—C13 1.489 (7)
C1—C2 1.384 (9) C11—C12 1.360 (7)
C2—C3 1.371 (9) C11—H11 0.9300
C3—C4 1.326 (14) C12—H12 0.9300
C3—H3 0.9300
O4—S1—O3 119.6 (3) C5—C6—C1 121.5 (8)
O4—S1—N1 108.3 (3) C5—C6—H6 119.3
O3—S1—N1 104.7 (3) C1—C6—H6 119.3
O4—S1—C1 107.3 (3) C8—C7—C12 119.0 (5)
O3—S1—C1 109.8 (3) C8—C7—N1 122.9 (5)
N1—S1—C1 106.4 (2) C12—C7—N1 118.1 (5)
C13—O1—H1O 109.5 C7—C8—C9 120.5 (5)
C7—N1—S1 125.6 (4) C7—C8—H8 119.7
C7—N1—H1 117.2 C9—C8—H8 119.7
S1—N1—H1 117.2 C8—C9—C10 121.3 (5)
C6—C1—C2 118.7 (6) C8—C9—Cl1 116.1 (4)
C6—C1—S1 117.2 (6) C10—C9—Cl1 122.5 (4)
C2—C1—S1 124.1 (5) C11—C10—C9 116.2 (5)
C3—C2—C1 120.3 (7) C11—C10—C13 119.4 (4)
C3—C2—I1 115.4 (6) C9—C10—C13 124.4 (5)
C1—C2—I1 124.3 (5) C12—C11—C10 122.8 (5)
C4—C3—C2 119.8 (9) C12—C11—H11 118.6
C4—C3—H3 120.1 C10—C11—H11 118.6
C2—C3—H3 120.1 C11—C12—C7 120.0 (5)
C3—C4—C5 122.4 (9) C11—C12—H12 120.0
C3—C4—H4 118.8 C7—C12—H12 120.0
C5—C4—H4 118.8 O2—C13—O1 122.6 (5)
C6—C5—C4 117.2 (9) O2—C13—C10 126.4 (5)
C6—C5—H5 121.4 O1—C13—C10 111.0 (5)
C4—C5—H5 121.4
O4—S1—N1—C7 −58.9 (5) S1—N1—C7—C8 30.4 (7)
O3—S1—N1—C7 172.4 (4) S1—N1—C7—C12 −150.9 (4)
C1—S1—N1—C7 56.2 (5) C12—C7—C8—C9 −1.7 (8)
O4—S1—C1—C6 −8.9 (5) N1—C7—C8—C9 177.0 (5)
O3—S1—C1—C6 122.5 (5) C7—C8—C9—C10 −2.8 (8)
N1—S1—C1—C6 −124.7 (5) C7—C8—C9—Cl1 178.5 (4)
O4—S1—C1—C2 173.7 (5) C8—C9—C10—C11 5.3 (7)
O3—S1—C1—C2 −54.9 (5) Cl1—C9—C10—C11 −176.1 (4)
N1—S1—C1—C2 57.9 (5) C8—C9—C10—C13 −173.7 (5)
C6—C1—C2—C3 0.5 (9) Cl1—C9—C10—C13 4.9 (7)
S1—C1—C2—C3 177.9 (5) C9—C10—C11—C12 −3.6 (8)
C6—C1—C2—I1 179.7 (4) C13—C10—C11—C12 175.5 (5)
S1—C1—C2—I1 −3.0 (7) C10—C11—C12—C7 −0.7 (8)
C1—C2—C3—C4 −0.6 (11) C8—C7—C12—C11 3.4 (8)
I1—C2—C3—C4 −179.8 (6) N1—C7—C12—C11 −175.3 (5)
C2—C3—C4—C5 0.9 (14) C11—C10—C13—O2 −178.6 (5)
C3—C4—C5—C6 −1.2 (14) C9—C10—C13—O2 0.3 (9)
C4—C5—C6—C1 1.1 (12) C11—C10—C13—O1 0.3 (7)
C2—C1—C6—C5 −0.9 (10) C9—C10—C13—O1 179.2 (5)
S1—C1—C6—C5 −178.4 (6)
Open in a new tab

Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
N1—H1···O2i 0.86 2.38 3.214 (6) 162
O1—H1O···O2ii 0.82 2.09 2.771 (6) 140
Open in a new tab

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+3/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5865).

References

  1. Arshad, M. N., Khan, I. U., Zia-ur-Rehman, M. & Shafiq, M. (2011). Asian J. Chem. 23, 2801–2805.
  2. Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Sharif, H. M. A. (2009b). Acta Cryst. E65, o831. [DOI] [PMC free article] [PubMed]
  3. Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Siddiqui, W. A. (2008). Acta Cryst. E64, o2045. [DOI] [PMC free article] [PubMed]
  4. Arshad, M. N., Tahir, M. N., Khan, I. U., Siddiqui, W. A. & Shafiq, M. (2009a). Acta Cryst. E65, o281. [DOI] [PMC free article] [PubMed]
  5. Arshad, M. N., Tahir, M. N., Khan, I. U., Siddiqui, W. A. & Shafiq, M. (2009c). Acta Cryst. E65, o230. [DOI] [PMC free article] [PubMed]
  6. Bruker (2007). SADABS, APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  7. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
  8. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
  9. Medina, J. C., Roche, D., Shan, B., Learned, R. M., Frankmoelle, W. P., Clark, D. L., Rosen, T. & Jaen, J. C. (1999). Bioorg. Med. Chem. Lett. 9, 1843–1846. [DOI] [PubMed]
  10. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  11. Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016412/hb5865sup1.cif

e-67-o1327-sup1.cif (17.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016412/hb5865Isup2.hkl

e-67-o1327-Isup2.hkl (176.2KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811016412/hb5865Isup3.cml

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

RESOURCES