PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o230.
Published online 2009 January 8. doi:  10.1107/S1600536808043754
PMCID: PMC2968366

4-(2-Iodo­benzene­sulfonamido)benzoic acid monohydrate

Abstract

In the mol­ecule of the title compound, C13H10INO4S·H2O, the coordination around the S atom is distorted tetra­hedral. The aromatic rings are oriented at a dihedral angle of 74.18 (17)°. Intra­molecular C—H(...)O hydrogen bonds result in the formation of non-planar five- and six-membered rings, which adopt envelope and twist conformations, respectively. In the crystal structure, inter­molecular N—H(...)O, O—H(...)O and C—H(...)O hydrogen bonds link the mol­ecules. π–π Contacts between the phenyl rings [centroid–centroid distance = 3.726 (3) Å] may further stabilize the structure. There is also a C—H(...)π inter­action.

Related literature

For general background, see: Medina et al. (1999 [triangle]). For related structures, see: Arshad et al. (2008a [triangle],b [triangle]); Nan & Xing (2006 [triangle]); Deng & Mani (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o230-scheme1.jpg

Experimental

Crystal data

  • C13H10INO4S·H2O
  • M r = 421.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o230-efi1.jpg
  • a = 13.8049 (9) Å
  • b = 8.2756 (5) Å
  • c = 14.7928 (10) Å
  • β = 117.472 (3)°
  • V = 1499.42 (17) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.30 mm−1
  • T = 296 (2) K
  • 0.28 × 0.10 × 0.07 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.754, T max = 0.849
  • 9099 measured reflections
  • 3687 independent reflections
  • 2022 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.112
  • S = 1.01
  • 3687 reflections
  • 193 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.54 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/S1600536808043754/hk2605sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043754/hk2605Isup2.hkl

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

Acknowledgments

MNA greatfully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing him with a Scholaship under the Indigenous PhD Program (PIN 042–120607-PS2–183).

supplementary crystallographic information

Comment

The title compound belongs to the sulfonamide family of the organic compounds. This class of compounds is used as antibecterial agent. The halogenated sulfonamide is used as an inhibitor 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., 2008a,b), the title compound has been prepared, which will be utilized for the syntheses of biologically active heterocyclic molecules with thiazine moiety, and we report herein its crystal structure.

In the title compound, (I), (Fig 1), 2-iodophenyl and p-aminobenzoic acid moieties are connected through the SO2 group. The structure of (I) differs from 4-(tosylamino)benzoic acid, (II) (Nan & Xing, 2006), mainly due to the attachment of the iodo group at ortho position instead of methyl group at the para-position. 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 74.18 (17)°. The intramolecular C-H···O hydrogen bonds (Table 1) result in the formations of nonplanar five- and six-membered rings: C (S1/O1/C1/C6/H6) and D (S1/O1/N1/C7/C12/H12). Ring C adopts envelope conformation with O1 atom displaced by -0.172 (3) Å from the plane of the other rings atoms, while ring D has twisted conformation.

In the crystal structure, intermolecular N-H···O, O-H···O and C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. The π-π contact between the phenyl rings, Cg1—Cg1i [symmetry code: (i) -x, -y, -z, where Cg1 is centroid of the ring A (C1-C6)] may further stabilize the structure, with centroid-centroid distance of 3.726 (3) Å. There also exists a C–H···π interaction (Table 1).

Experimental

The title compound was synthesized according to a literature method (Deng & Mani, 2006). 4-Aminobenzoic acid (0.23 g, 1.67 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

H3O (for OH) atom was located in difference syntheses and refined [O-H = 0.91 (7) Å, Uiso(H) = 1.2Ueq(O)]. The remaining H atoms were positioned geometrically, with O-H = 0.81 and 0.88 Å (for H2O), 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,O).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% 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

C13H10INO4S·H2OF(000) = 824
Mr = 421.20Dx = 1.866 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3638 reflections
a = 13.8049 (9) Åθ = 2.8–28.3°
b = 8.2756 (5) ŵ = 2.30 mm1
c = 14.7928 (10) ÅT = 296 K
β = 117.472 (3)°Needle, light brown
V = 1499.42 (17) Å30.28 × 0.10 × 0.07 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer3687 independent reflections
Radiation source: fine-focus sealed tube2022 reflections with I > 2σ(I)
graphiteRint = 0.041
Detector resolution: 7.40 pixels mm-1θmax = 28.3°, θmin = 2.8°
ω scansh = −15→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −11→6
Tmin = 0.754, Tmax = 0.849l = −19→19
9099 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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0445P)2] where P = (Fo2 + 2Fc2)/3
3687 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.55 e Å3
1 restraintΔρmin = −0.54 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*/Ueq
I10.05915 (3)−0.04749 (5)0.26394 (3)0.0542 (2)
S10.25343 (9)0.13703 (16)0.19929 (10)0.0345 (4)
O10.3085 (3)0.2410 (4)0.1612 (3)0.0454 (14)
O20.2710 (3)−0.0328 (4)0.2010 (3)0.0415 (11)
O30.4294 (3)0.7980 (5)0.6032 (3)0.0614 (17)
O40.3555 (4)0.9284 (5)0.4580 (3)0.0710 (17)
O50.4923 (3)0.4220 (5)0.1937 (3)0.086 (2)
N10.2852 (3)0.1876 (5)0.3139 (3)0.0377 (16)
C10.1119 (4)0.1750 (5)0.1231 (4)0.0292 (17)
C20.0316 (4)0.1050 (6)0.1405 (4)0.0363 (19)
C3−0.0775 (4)0.1337 (7)0.0725 (5)0.051 (2)
C4−0.1052 (5)0.2319 (8)−0.0099 (5)0.056 (2)
C5−0.0257 (5)0.2994 (7)−0.0279 (4)0.054 (2)
C60.0834 (4)0.2707 (6)0.0389 (4)0.044 (2)
C70.3051 (3)0.3426 (6)0.3580 (4)0.0331 (18)
C80.3537 (4)0.3529 (6)0.4634 (4)0.0392 (19)
C90.3778 (4)0.5001 (6)0.5106 (4)0.0378 (17)
C100.3543 (3)0.6425 (6)0.4554 (4)0.0327 (16)
C110.3061 (4)0.6315 (6)0.3498 (4)0.0391 (19)
C120.2810 (4)0.4842 (6)0.3012 (4)0.0397 (17)
C130.3791 (4)0.8042 (7)0.5038 (5)0.0417 (19)
H10.290970.109160.354210.0453*
H3−0.132130.085380.083340.0614*
H3O0.440 (5)0.896 (8)0.634 (5)0.0734*
H4−0.178270.25271−0.053780.0676*
H5−0.044480.36446−0.084810.0649*
H60.137570.316700.026520.0534*
H80.369970.259030.502160.0469*
H90.410640.504650.581380.0457*
H110.290450.725580.311260.0474*
H120.247910.479360.230470.0474*
H5A0.552250.437140.241630.1030*
H5B0.448250.357540.205130.1030*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I10.0626 (3)0.0469 (3)0.0680 (3)0.0006 (2)0.0429 (2)0.0116 (2)
S10.0343 (6)0.0313 (8)0.0384 (9)−0.0025 (6)0.0171 (6)−0.0039 (6)
O10.049 (2)0.043 (2)0.056 (3)−0.0132 (17)0.0343 (19)−0.0061 (19)
O20.0403 (19)0.029 (2)0.050 (2)0.0031 (16)0.0165 (17)−0.0062 (18)
O30.086 (3)0.032 (3)0.043 (3)0.003 (2)0.010 (2)−0.007 (2)
O40.105 (3)0.027 (3)0.045 (3)0.005 (2)0.004 (2)0.005 (2)
O50.046 (2)0.076 (4)0.100 (4)−0.015 (2)0.003 (2)0.054 (3)
N10.053 (3)0.023 (2)0.029 (3)−0.0021 (19)0.012 (2)0.003 (2)
C10.035 (3)0.024 (3)0.028 (3)0.002 (2)0.014 (2)−0.001 (2)
C20.039 (3)0.028 (3)0.044 (4)0.002 (2)0.021 (3)−0.007 (2)
C30.043 (3)0.042 (4)0.070 (5)−0.003 (3)0.027 (3)−0.016 (3)
C40.046 (3)0.051 (4)0.049 (4)0.008 (3)0.002 (3)−0.011 (3)
C50.073 (4)0.041 (4)0.032 (4)0.009 (3)0.010 (3)−0.001 (3)
C60.054 (3)0.037 (4)0.040 (4)−0.005 (3)0.020 (3)−0.003 (3)
C70.030 (2)0.028 (3)0.038 (4)0.000 (2)0.013 (2)−0.004 (3)
C80.052 (3)0.023 (3)0.041 (4)0.001 (2)0.020 (3)0.006 (3)
C90.050 (3)0.028 (3)0.033 (3)0.000 (2)0.017 (3)0.001 (2)
C100.028 (2)0.032 (3)0.035 (3)−0.002 (2)0.012 (2)−0.002 (3)
C110.044 (3)0.023 (3)0.046 (4)0.000 (2)0.017 (3)0.007 (3)
C120.050 (3)0.033 (3)0.027 (3)0.001 (2)0.010 (3)0.003 (2)
C130.036 (3)0.030 (3)0.048 (4)0.004 (2)0.010 (3)0.002 (3)

Geometric parameters (Å, °)

I1—C22.105 (5)C5—C61.389 (9)
S1—O11.425 (4)C7—C81.387 (7)
S1—O21.425 (4)C7—C121.390 (7)
S1—N11.599 (4)C8—C91.367 (7)
S1—C11.776 (6)C9—C101.384 (7)
O3—C131.306 (8)C10—C131.481 (8)
O4—C131.191 (7)C10—C111.390 (7)
O3—H3O0.91 (7)C11—C121.376 (7)
O5—H5A0.8100C3—H30.9300
O5—H5B0.8800C4—H40.9300
N1—C71.408 (6)C5—H50.9300
N1—H10.8600C6—H60.9300
C1—C21.376 (8)C8—H80.9300
C1—C61.372 (7)C9—H90.9300
C2—C31.392 (9)C11—H110.9300
C3—C41.365 (9)C12—H120.9300
C4—C51.363 (10)
I1···O23.456 (5)C4···O2iv3.158 (8)
I1···N13.456 (4)C4···I1xi3.853 (7)
I1···C4i3.853 (7)C5···C5xii3.416 (8)
I1···C2i3.671 (5)C8···O1xiii3.353 (7)
I1···C3i3.509 (6)C9···C9x3.530 (9)
I1···H13.1200C12···O13.035 (7)
S1···H122.8800C13···O5v3.379 (7)
S1···H5Aii2.9200C9···H3xi3.1000
O1···O52.791 (6)C10···H3xi2.8900
O1···C123.035 (7)C11···H3xi3.0100
O1···C8iii3.353 (7)H1···I13.1200
O2···C4iv3.158 (8)H1···H82.3100
O2···O5ii2.924 (6)H1···O4ix2.0300
O2···I13.456 (5)H3···C10i2.8900
O3···O5v2.616 (6)H3···C9i3.1000
O4···N1vi2.860 (6)H3···C11i3.0100
O5···O3vii2.616 (6)H3O···O5v1.73 (7)
O5···C13vii3.379 (7)H3O···H5Av2.1400
O5···O2viii2.924 (6)H3O···H5Bv2.2700
O5···O12.791 (6)H4···O2iv2.6700
O1···H122.5400H5A···O2viii2.2000
O1···H5B1.9800H5A···H9x2.4700
O1···H62.3600H5A···S1viii2.9200
O1···H8iii2.8500H5A···H3Ovii2.1400
O2···H4iv2.6700H5B···O11.9800
O2···H11ix2.5200H5B···O3x2.8500
O2···H5Aii2.2000H5B···H3Ovii2.2700
O3···H92.4500H6···O12.3600
O3···H5Bx2.8500H8···O4ix2.8000
O4···H1vi2.0300H8···H12.3100
O4···H8vi2.8000H8···O1xiii2.8500
O4···H112.5600H9···O32.4500
O5···H3Ovii1.73 (7)H9···H5Ax2.4700
N1···O4ix2.860 (6)H11···O2vi2.5200
N1···I13.456 (4)H11···O42.5600
C2···I1xi3.671 (5)H12···O12.5400
C3···I1xi3.509 (6)H12···S12.8800
O1—S1—O2119.0 (3)C8—C9—C10121.5 (5)
O1—S1—N1109.0 (2)C9—C10—C11117.9 (5)
O1—S1—C1105.9 (2)C11—C10—C13119.1 (5)
O2—S1—N1106.2 (2)C9—C10—C13123.0 (5)
O2—S1—C1108.3 (2)C10—C11—C12121.3 (5)
N1—S1—C1108.1 (3)C7—C12—C11119.9 (5)
C13—O3—H3O114 (4)O3—C13—C10113.2 (5)
H5A—O5—H5B116.00O4—C13—C10124.3 (6)
S1—N1—C7129.0 (4)O3—C13—O4122.6 (6)
C7—N1—H1116.00C2—C3—H3120.00
S1—N1—H1115.00C4—C3—H3120.00
S1—C1—C2123.5 (4)C5—C4—H4120.00
S1—C1—C6116.7 (5)C3—C4—H4120.00
C2—C1—C6119.6 (5)C4—C5—H5120.00
I1—C2—C1125.2 (4)C6—C5—H5120.00
C1—C2—C3119.3 (5)C5—C6—H6120.00
I1—C2—C3115.6 (4)C1—C6—H6120.00
C2—C3—C4120.7 (6)C7—C8—H8120.00
C3—C4—C5120.0 (6)C9—C8—H8120.00
C4—C5—C6119.9 (5)C10—C9—H9119.00
C1—C6—C5120.5 (6)C8—C9—H9119.00
C8—C7—C12119.0 (5)C10—C11—H11119.00
N1—C7—C8117.8 (4)C12—C11—H11119.00
N1—C7—C12123.2 (5)C7—C12—H12120.00
C7—C8—C9120.4 (5)C11—C12—H12120.00
O1—S1—N1—C735.5 (5)C1—C2—C3—C4−0.9 (9)
O2—S1—N1—C7164.9 (5)C2—C3—C4—C51.9 (10)
C1—S1—N1—C7−79.1 (5)C3—C4—C5—C6−1.3 (9)
O1—S1—C1—C2−175.7 (4)C4—C5—C6—C1−0.1 (8)
O1—S1—C1—C69.1 (4)N1—C7—C8—C9178.2 (5)
O2—S1—C1—C255.6 (5)C12—C7—C8—C9−0.2 (9)
O2—S1—C1—C6−119.7 (4)N1—C7—C12—C11−177.8 (5)
N1—S1—C1—C2−59.0 (5)C8—C7—C12—C110.4 (9)
N1—S1—C1—C6125.7 (4)C7—C8—C9—C100.3 (9)
S1—N1—C7—C8−166.5 (4)C8—C9—C10—C11−0.6 (9)
S1—N1—C7—C1211.8 (8)C8—C9—C10—C13180.0 (6)
S1—C1—C2—I14.0 (6)C9—C10—C11—C120.9 (9)
S1—C1—C2—C3−175.7 (4)C13—C10—C11—C12−179.7 (6)
C6—C1—C2—I1179.1 (4)C9—C10—C13—O32.8 (8)
C6—C1—C2—C3−0.5 (8)C9—C10—C13—O4−176.6 (6)
S1—C1—C6—C5176.5 (4)C11—C10—C13—O3−176.6 (5)
C2—C1—C6—C51.0 (8)C11—C10—C13—O44.0 (9)
I1—C2—C3—C4179.4 (5)C10—C11—C12—C7−0.8 (9)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O4ix0.862.032.860 (6)161.00
O3—H3O···O5v0.91 (7)1.73 (7)2.616 (6)165 (7)
O5—H5A···O2viii0.812.202.924 (6)149.00
O5—H5B···O10.881.982.791 (6)152.00
C6—H6···O10.932.362.793 (7)108.00
C11—H11···O2vi0.932.523.437 (6)171.00
C12—H12···O10.932.543.035 (7)114.00
C3—H3···Cg2i0.932.903.818 (7)168.00

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2605).

References

  • Arshad, M. N., Tahir, M. N., Khan, I. U., Ahmad, E. & Shafiq, M. (2008a). Acta Cryst. E64, o2380. [PMC free article] [PubMed]
  • Arshad, M. N., Tahir, M. N., Khan, I. U., Shafiq, M. & Siddiqui, W. A. (2008b). Acta Cryst. E64, m1628. [PMC free article] [PubMed]
  • Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc. Madison, Wisconsin, USA.
  • Deng, X. & Mani, N. S. (2006). Green Chem 8, 835–838.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • 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. [PubMed]
  • Nan, Z.-H. & Xing, J.-D. (2006). Acta Cryst. E62, o1978–o1979.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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