2-Chloro-6-(2,3-di­chloro­benzene­sulfonamido)­benzoic acid

Ayesha Munir; Hafiz Mubashar-ur-Rehman; Abdullah M Asiri; Islam Ullah Khan; Muhammad Nadeem Arshad

doi:10.1107/S1600536813011574

. 2013 May 4;69(Pt 6):o832. doi: 10.1107/S1600536813011574

2-Chloro-6-(2,3-dichlorobenzenesulfonamido)benzoic acid

Ayesha Munir ^a, Hafiz Mubashar-ur-Rehman ^a,^*, Abdullah M Asiri ^b,^c, Islam Ullah Khan ^a, Muhammad Nadeem Arshad ^c,^*

PMCID: PMC3684920 PMID: 23795022

Abstract

In the title compound, C₁₃H₈Cl₃NO₄S, the aromatic rings are oriented at a dihedral angle of 68.94 (1)° and the molecule adopts a V-shape. An intramolecular N—H⋯O interaction generates a six-membered S(6) ring motif. In the crystal, pairs of O—H⋯O hydrogen bonds involving the carboxy group link the molecules into inversion dimers with an R ₂ ²(8) motif. N—H⋯O and non-classical C—H⋯O interactions connect the molecules, forming sheets propagating in (100).

Related literature

For the synthesis, see: Arshad et al. (2012 ▶) For related structures, see: Arshad et al. (2009 ▶, 2011 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₃H₈Cl₃NO₄S
M _r = 380.61
Monoclinic,
a = 9.0164 (3) Å
b = 18.6017 (5) Å
c = 9.8574 (3) Å
β = 111.653 (3)°
V = 1536.62 (8) Å³
Z = 4
Cu Kα radiation
μ = 6.83 mm⁻¹
T = 296 K
0.38 × 0.20 × 0.18 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas, CCD) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.467, T _max = 1.000
11742 measured reflections
3018 independent reflections
2597 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.104
S = 1.04
3018 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and X-SEED (Barbour, 2001 ▶).

Supplementary Material

Click here for additional data file.^{(22.2KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813011574/hg5312sup1.cif

e-69-0o832-sup1.cif^{(22.2KB, cif)}

Click here for additional data file.^{(148.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011574/hg5312Isup2.hkl

e-69-0o832-Isup2.hkl^{(148.1KB, hkl)}

Click here for additional data file.^{(5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813011574/hg5312Isup3.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⋯O3	0.86	2.55	2.940 (2)	108
C12—H12⋯O3ⁱ	0.93	2.59	3.425 (3)	150
O3—H3⋯O4ⁱⁱ	0.82	1.85	2.666 (2)	176
N1—H1⋯O2ⁱⁱⁱ	0.86	2.30	3.128 (2)	162
C5—H5⋯O4^iv	0.93	2.53	3.256 (4)	135
C10—H10⋯O1^v	0.93	2.51	3.165 (3)	127

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

The authors would like to thank the Deanship of Scientific Research at King Abdulaziz University for the support of this research via the Research Group Track of Grant No. (3-102/428).

supplementary crystallographic information

Comment

In connection to synthesis of halogenated sulfonamide derivatives 2-Chloro-4-(2-iodobenzenesulfonamido)benzoic acid (Arshad et al., 2011) and 2-Chloro-5-(2-iodobenzenesulfonamido)benzoic acid (Arshad et al., 2009), we are reporting the crystal structure of title compound.

The two aromatic rings [(C1—C6) & (C7—C12)] in the structure of molecule are oriented at dihedral angle of 68.94 (1)°. The carboxylic group (C13/O3/O4) is twisted at 58.11 (1)° with respect to its mother aromatic ring (C7—C12) and its atoms C13, O3 & O4 are away by -0.1938 (35)Å , 0.6924 (39)Å , -1.1739 (39)Å repectively from the mean plane generating from atoms C7/C8/C9/C10/C11/C12 with the r.m.s deviation of 0.0183 (15) Å. The amino and carboxylic groups are involved in classical N1—H1···O3 intramolecular hydrogen bonding interaction and produce six membered ring motif S¹₁ (6) (Bernstein et al. 1995) which is oriented at dihedral angles of 54.30 (11)° & 18.98 (12)° with respect to two aromatic rings [(C1—C6) & (C7—C12)], respectively. On the other hand the amino group get connected with oxygen of SO₂ to form intermolecular N1—H1···O2 hydrogen bond. The carboxylic group gives typical inversion dimerization by generating eight membered ring motif R²₂ (8) (Bernstein et al. 1995) through O3—H3···O4 interaction. The non-clasical C—H···O type interaction have also been observed in the molecule (Fig. 2) for which symmetry detail are available in Table 1.

Experimental

The title compound was synthesised following the literature method (Arshad et al., 2012) and recrystallized from ethylacetate under slow evaporation at room temperature.