organic compounds
4-(3-Chloro-2,2-dimethylpropanamido)benzenesulfonamide
aDepartment of Physics, Faculty of Arts and Sciences, Harran University, 63300 Şanlıurfa, Turkey, bCentral Research Lab, Harran University, Osmanbey Campus, 63300 Şanlıurfa, Turkey, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and dDepartment of Chemistry, Faculty of Arts and Sciences, Harran University, 63300 Şanlıurfa, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
In the title compound, C11H15ClN2O3S, the 3-chloro-2,2-dimethylpropanamide and sulfonamide substituents are arranged on opposite sides of the benzene ring plane. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network.
Related literature
For the antibacterial, antimicrobial and antiglaucoma activity of et al. (2005); Supuran & Scozzafava (2000). For related structures, see: Akkurt et al. (2010); Idemudia et al. (2012); Asiri et al. (2012). For the synthesis, see: Türkmen et al. (2011).
and their derivatives and for their physical properties and pharmacological applications, see: PoulsenExperimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2005); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812046806/sj5282sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812046806/sj5282Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812046806/sj5282Isup3.cml
Nucleophilic acyl substitution of 3-chloro-2,2-dimethyl-propanoylchloride with sulfanilamide gave the title compound as described previously (Türkmen et al., 2011). Crystals suitable for X-ray diffraction studies were grown by slow evaporation of an ethanol, chloroform, dichloromethane (4/3/3 v/v) solution of the product.
The H atoms on the NH and NH2 groups were located from a difference Fourier map and refined with distance restraints of N—H = 0.88 (1) Å for the NH2, with Uiso(H) = 1.2Ueq(N). The remaining H atoms were positioned geometrically, with C—H = 0.93–0.97 Å, and refined as riding with Uiso(H) = 1.2 or 1.5 Ueq(C). The high
low ratio of observed to unique reflections and relatively high su values indicate that the crystals were of rather poor quality and did not diffract strongly.Data collection: CrystalClear (Rigaku/MSC, 2005); cell
CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).Fig. 1. The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. | |
Fig. 2. Packing of the title compound viewed along the b axis with N—H···O and C—H···O hydrogen bonds drawn as dashed lines. H atoms not involved in hydrogen bonding are omitted for clarity. |
C11H15ClN2O3S | F(000) = 608 |
Mr = 290.77 | Dx = 1.392 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5710 reflections |
a = 20.4359 (11) Å | θ = 2.5–30.5° |
b = 7.2437 (4) Å | µ = 0.43 mm−1 |
c = 9.4693 (5) Å | T = 294 K |
β = 98.222 (3)° | Needle, white |
V = 1387.35 (13) Å3 | 0.31 × 0.14 × 0.13 mm |
Z = 4 |
Rigaku R-AXIS RAPID-S diffractometer | 4240 independent reflections |
Radiation source: Sealed Tube | 2054 reflections with I > 2σ(I) |
Graphite Monochromator monochromator | Rint = 0.000 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 30.6°, θmin = 3.0° |
ω scans | h = −29→28 |
Absorption correction: part of the (XABS2; Parkin et al., 1995) | model (ΔF) k = 0→10 |
Tmin = 0.931, Tmax = 0.946 | l = 0→13 |
4240 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)] = 0.084 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.231 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0751P)2 + 1.0033P] where P = (Fo2 + 2Fc2)/3 |
4240 reflections | (Δ/σ)max < 0.001 |
175 parameters | Δρmax = 0.36 e Å−3 |
2 restraints | Δρmin = −0.33 e Å−3 |
C11H15ClN2O3S | V = 1387.35 (13) Å3 |
Mr = 290.77 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 20.4359 (11) Å | µ = 0.43 mm−1 |
b = 7.2437 (4) Å | T = 294 K |
c = 9.4693 (5) Å | 0.31 × 0.14 × 0.13 mm |
β = 98.222 (3)° |
Rigaku R-AXIS RAPID-S diffractometer | 4240 independent reflections |
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995) | 2054 reflections with I > 2σ(I) |
Tmin = 0.931, Tmax = 0.946 | Rint = 0.000 |
4240 measured reflections |
R[F2 > 2σ(F2)] = 0.084 | 2 restraints |
wR(F2) = 0.231 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.36 e Å−3 |
4240 reflections | Δρmin = −0.33 e Å−3 |
175 parameters |
Experimental. Absorption correction: (XABS2; Parkin et al., 1995) Cubic fit to sin(theta)/lambda - 24 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 on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.05415 (8) | 0.1450 (2) | 0.13028 (15) | 0.1040 (6) | |
S1 | 0.43958 (5) | −0.22940 (14) | 0.07872 (10) | 0.0540 (3) | |
O1 | 0.45415 (14) | −0.1736 (4) | −0.0593 (3) | 0.0634 (10) | |
O2 | 0.42131 (15) | −0.4163 (4) | 0.1004 (3) | 0.0684 (11) | |
O3 | 0.19397 (15) | 0.3907 (4) | 0.0227 (3) | 0.0689 (10) | |
N1 | 0.50493 (18) | −0.1856 (5) | 0.1885 (3) | 0.0592 (11) | |
N2 | 0.22555 (18) | 0.2516 (5) | 0.2354 (4) | 0.0640 (13) | |
C1 | 0.37522 (19) | −0.0863 (6) | 0.1199 (4) | 0.0550 (14) | |
C2 | 0.3682 (2) | 0.0917 (6) | 0.0669 (4) | 0.0603 (14) | |
C3 | 0.3193 (2) | 0.2057 (6) | 0.1041 (4) | 0.0628 (17) | |
C4 | 0.2770 (2) | 0.1406 (6) | 0.1935 (4) | 0.0579 (14) | |
C5 | 0.2852 (2) | −0.0344 (7) | 0.2500 (4) | 0.0691 (17) | |
C6 | 0.3339 (2) | −0.1493 (7) | 0.2132 (4) | 0.0675 (16) | |
C7 | 0.1859 (2) | 0.3629 (6) | 0.1465 (4) | 0.0563 (14) | |
C8 | 0.1294 (2) | 0.4544 (6) | 0.2119 (4) | 0.0643 (16) | |
C9 | 0.0901 (3) | 0.5785 (8) | 0.1019 (6) | 0.102 (3) | |
C10 | 0.1581 (3) | 0.5664 (8) | 0.3447 (6) | 0.102 (3) | |
C11 | 0.0849 (2) | 0.3082 (7) | 0.2637 (5) | 0.0727 (18) | |
H1N | 0.519 (3) | −0.074 (3) | 0.174 (6) | 0.1230* | |
H2 | 0.39660 | 0.13480 | 0.00580 | 0.0720* | |
H2N | 0.500 (3) | −0.209 (8) | 0.277 (2) | 0.1230* | |
H3 | 0.31500 | 0.32570 | 0.06900 | 0.0750* | |
H3N | 0.213 (3) | 0.216 (8) | 0.320 (6) | 0.1230* | |
H5 | 0.25770 | −0.07550 | 0.31350 | 0.0830* | |
H6 | 0.33890 | −0.26790 | 0.25080 | 0.0810* | |
H9A | 0.11770 | 0.67740 | 0.07780 | 0.1520* | |
H9B | 0.05290 | 0.62860 | 0.14050 | 0.1520* | |
H9C | 0.07470 | 0.50810 | 0.01780 | 0.1520* | |
H10A | 0.18810 | 0.65780 | 0.31830 | 0.1530* | |
H10B | 0.18120 | 0.48500 | 0.41480 | 0.1530* | |
H10C | 0.12270 | 0.62620 | 0.38370 | 0.1530* | |
H11A | 0.04780 | 0.36890 | 0.29760 | 0.0870* | |
H11B | 0.10950 | 0.24310 | 0.34380 | 0.0870* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1001 (11) | 0.1304 (13) | 0.0862 (9) | −0.0399 (9) | 0.0299 (8) | −0.0167 (8) |
S1 | 0.0632 (6) | 0.0599 (6) | 0.0404 (5) | −0.0007 (5) | 0.0126 (4) | 0.0005 (4) |
O1 | 0.079 (2) | 0.0732 (19) | 0.0411 (14) | 0.0032 (15) | 0.0195 (13) | −0.0002 (12) |
O2 | 0.083 (2) | 0.0627 (18) | 0.0608 (17) | −0.0105 (15) | 0.0144 (15) | −0.0004 (14) |
O3 | 0.0708 (19) | 0.090 (2) | 0.0481 (15) | 0.0074 (16) | 0.0166 (13) | 0.0051 (14) |
N1 | 0.063 (2) | 0.068 (2) | 0.0475 (18) | −0.0015 (17) | 0.0115 (16) | 0.0033 (16) |
N2 | 0.063 (2) | 0.084 (3) | 0.0473 (18) | 0.0104 (19) | 0.0163 (16) | 0.0035 (18) |
C1 | 0.058 (2) | 0.066 (3) | 0.0420 (19) | −0.0019 (19) | 0.0104 (16) | 0.0019 (17) |
C2 | 0.061 (2) | 0.070 (3) | 0.053 (2) | −0.001 (2) | 0.0190 (19) | 0.008 (2) |
C3 | 0.063 (3) | 0.065 (3) | 0.064 (3) | 0.003 (2) | 0.021 (2) | 0.008 (2) |
C4 | 0.056 (2) | 0.075 (3) | 0.044 (2) | 0.001 (2) | 0.0119 (17) | 0.0023 (19) |
C5 | 0.067 (3) | 0.086 (3) | 0.059 (3) | 0.003 (2) | 0.025 (2) | 0.015 (2) |
C6 | 0.067 (3) | 0.079 (3) | 0.059 (2) | 0.008 (2) | 0.018 (2) | 0.017 (2) |
C7 | 0.058 (2) | 0.069 (3) | 0.044 (2) | −0.003 (2) | 0.0143 (17) | 0.0006 (18) |
C8 | 0.074 (3) | 0.070 (3) | 0.053 (2) | 0.008 (2) | 0.023 (2) | 0.002 (2) |
C9 | 0.113 (5) | 0.104 (4) | 0.098 (4) | 0.042 (4) | 0.048 (3) | 0.032 (3) |
C10 | 0.125 (5) | 0.090 (4) | 0.097 (4) | −0.007 (3) | 0.035 (4) | −0.030 (3) |
C11 | 0.073 (3) | 0.095 (4) | 0.054 (2) | 0.008 (3) | 0.023 (2) | 0.002 (2) |
Cl1—C11 | 1.778 (5) | C7—C8 | 1.536 (6) |
S1—O1 | 1.439 (3) | C8—C9 | 1.516 (7) |
S1—O2 | 1.427 (3) | C8—C10 | 1.540 (7) |
S1—N1 | 1.602 (4) | C8—C11 | 1.522 (6) |
S1—C1 | 1.762 (4) | C2—H2 | 0.9300 |
O3—C7 | 1.224 (5) | C3—H3 | 0.9300 |
N2—C4 | 1.424 (6) | C5—H5 | 0.9300 |
N2—C7 | 1.349 (5) | C6—H6 | 0.9300 |
N1—H1N | 0.88 (3) | C9—H9A | 0.9600 |
N1—H2N | 0.88 (2) | C9—H9B | 0.9600 |
N2—H3N | 0.91 (6) | C9—H9C | 0.9600 |
C1—C2 | 1.384 (6) | C10—H10A | 0.9600 |
C1—C6 | 1.384 (6) | C10—H10B | 0.9600 |
C2—C3 | 1.380 (6) | C10—H10C | 0.9600 |
C3—C4 | 1.377 (6) | C11—H11A | 0.9700 |
C4—C5 | 1.377 (6) | C11—H11B | 0.9700 |
C5—C6 | 1.380 (6) | ||
O1—S1—O2 | 119.30 (17) | C9—C8—C10 | 110.6 (4) |
O1—S1—N1 | 105.79 (17) | C9—C8—C11 | 110.6 (4) |
O1—S1—C1 | 107.08 (18) | Cl1—C11—C8 | 113.6 (3) |
O2—S1—N1 | 107.79 (18) | C1—C2—H2 | 120.00 |
O2—S1—C1 | 107.90 (19) | C3—C2—H2 | 120.00 |
N1—S1—C1 | 108.62 (19) | C2—C3—H3 | 120.00 |
C4—N2—C7 | 124.4 (4) | C4—C3—H3 | 120.00 |
H1N—N1—H2N | 115 (5) | C4—C5—H5 | 120.00 |
S1—N1—H1N | 110 (4) | C6—C5—H5 | 120.00 |
S1—N1—H2N | 113 (4) | C1—C6—H6 | 120.00 |
C4—N2—H3N | 113 (4) | C5—C6—H6 | 120.00 |
C7—N2—H3N | 120 (4) | C8—C9—H9A | 110.00 |
S1—C1—C2 | 120.7 (3) | C8—C9—H9B | 109.00 |
C2—C1—C6 | 119.9 (4) | C8—C9—H9C | 109.00 |
S1—C1—C6 | 119.4 (3) | H9A—C9—H9B | 109.00 |
C1—C2—C3 | 120.4 (4) | H9A—C9—H9C | 109.00 |
C2—C3—C4 | 119.6 (4) | H9B—C9—H9C | 109.00 |
N2—C4—C3 | 122.1 (4) | C8—C10—H10A | 109.00 |
N2—C4—C5 | 117.7 (4) | C8—C10—H10B | 109.00 |
C3—C4—C5 | 120.1 (4) | C8—C10—H10C | 109.00 |
C4—C5—C6 | 120.6 (4) | H10A—C10—H10B | 110.00 |
C1—C6—C5 | 119.4 (4) | H10A—C10—H10C | 109.00 |
O3—C7—C8 | 121.8 (4) | H10B—C10—H10C | 110.00 |
N2—C7—C8 | 115.2 (3) | Cl1—C11—H11A | 109.00 |
O3—C7—N2 | 123.0 (4) | Cl1—C11—H11B | 109.00 |
C10—C8—C11 | 106.2 (4) | C8—C11—H11A | 109.00 |
C7—C8—C11 | 110.4 (4) | C8—C11—H11B | 109.00 |
C7—C8—C9 | 109.5 (4) | H11A—C11—H11B | 108.00 |
C7—C8—C10 | 109.6 (4) | ||
O1—S1—C1—C2 | −29.3 (4) | C2—C3—C4—N2 | −179.9 (4) |
O1—S1—C1—C6 | 154.6 (3) | C2—C3—C4—C5 | 2.7 (6) |
O2—S1—C1—C2 | −158.9 (3) | N2—C4—C5—C6 | 179.7 (4) |
O2—S1—C1—C6 | 25.0 (4) | C3—C4—C5—C6 | −2.8 (6) |
N1—S1—C1—C2 | 84.5 (4) | C4—C5—C6—C1 | 0.8 (6) |
N1—S1—C1—C6 | −91.6 (4) | O3—C7—C8—C9 | −1.1 (6) |
C7—N2—C4—C3 | 42.6 (6) | O3—C7—C8—C10 | −122.6 (4) |
C7—N2—C4—C5 | −139.9 (4) | O3—C7—C8—C11 | 120.8 (4) |
C4—N2—C7—O3 | −6.2 (7) | N2—C7—C8—C9 | 178.6 (4) |
C4—N2—C7—C8 | 174.1 (4) | N2—C7—C8—C10 | 57.2 (5) |
S1—C1—C2—C3 | −177.4 (3) | N2—C7—C8—C11 | −59.4 (5) |
C6—C1—C2—C3 | −1.4 (6) | C7—C8—C11—Cl1 | −54.2 (4) |
S1—C1—C6—C5 | 177.4 (3) | C9—C8—C11—Cl1 | 67.1 (4) |
C2—C1—C6—C5 | 1.3 (6) | C10—C8—C11—Cl1 | −172.9 (3) |
C1—C2—C3—C4 | −0.6 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.88 (3) | 2.57 (5) | 3.035 (4) | 114 (4) |
N1—H1N···O1ii | 0.88 (3) | 2.21 (4) | 3.043 (5) | 160 (5) |
N1—H2N···O1iii | 0.88 (2) | 2.10 (4) | 2.921 (4) | 155 (5) |
N2—H3N···O3iv | 0.91 (6) | 2.16 (6) | 3.063 (5) | 173 (5) |
C3—H3···O3 | 0.93 | 2.49 | 2.896 (5) | 106 |
C6—H6···O2 | 0.93 | 2.59 | 2.936 (5) | 103 |
C11—H11B···O3iv | 0.97 | 2.44 | 3.391 (5) | 166 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y, −z; (iii) x, −y−1/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H15ClN2O3S |
Mr | 290.77 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 20.4359 (11), 7.2437 (4), 9.4693 (5) |
β (°) | 98.222 (3) |
V (Å3) | 1387.35 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.43 |
Crystal size (mm) | 0.31 × 0.14 × 0.13 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID-S diffractometer |
Absorption correction | Part of the refinement model (ΔF) (XABS2; Parkin et al., 1995) |
Tmin, Tmax | 0.931, 0.946 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4240, 4240, 2054 |
Rint | 0.000 |
(sin θ/λ)max (Å−1) | 0.716 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.084, 0.231, 1.02 |
No. of reflections | 4240 |
No. of parameters | 175 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.36, −0.33 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.88 (3) | 2.57 (5) | 3.035 (4) | 114 (4) |
N1—H1N···O1ii | 0.88 (3) | 2.21 (4) | 3.043 (5) | 160 (5) |
N1—H2N···O1iii | 0.88 (2) | 2.10 (4) | 2.921 (4) | 155 (5) |
N2—H3N···O3iv | 0.91 (6) | 2.16 (6) | 3.063 (5) | 173 (5) |
C11—H11B···O3iv | 0.97 | 2.44 | 3.391 (5) | 166 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1, −y, −z; (iii) x, −y−1/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
Acknowledgements
The authors thank the Unit of Scientific Research Projects of Harran University, Turkey for a research grant (HUBAK project Nos. 874 and 1136).
References
Akkurt, M., Yalçın, Ş. P., Türkmen, H. & Büyükgüngör, O. (2010). Acta Cryst. E66, o1559–o1560. Web of Science CSD CrossRef IUCr Journals Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Asiri, A. M., Faidallah, H. M., Alamry, K. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2258–o2259. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Idemudia, O. G., Sadimenko, A. P., Afolayan, A. J. & Hosten, E. C. (2012). Acta Cryst. E68, o1599. CSD CrossRef IUCr Journals Google Scholar
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53–56. CrossRef CAS Web of Science IUCr Journals Google Scholar
Poulsen, S., Bornaghi, L. F. & Healy, P. C. (2005). Bioorg. Med. Chem. Lett. 15, 5429–5433. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Supuran, C. T. & Scozzafava, A. (2000). Exp. Opin. Ther. Pat. 10, 575–600. CrossRef CAS Google Scholar
Türkmen, H., Zengin, G. & Buyukkircali, B. (2011). Bioorg. Chem. 39 114–119. Web of Science PubMed Google Scholar
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Sulfonamides are of interest because of their unique biological properties. They are known inhibitors of the carbonic anhydrase enzyme, currently used for the treatment of glaucoma in clinical medicine (Poulsen et al., 2005; Supuran & Scozzafava, 2000). The design and development of new sulfanilamide derivatives can help determine any structural requirements for improved biological activity. In this study, we have prepared and determined the crystal structure of 4-(3-Chloro-2,2-dimethylpropanoylamino)-benzenesulfonamide (I).
In Fig. 1, the molecular structure of the title compound is not planar. In the 3-chloro-2,2-dimethylpropanamide moiety of (I), the N2—C7—C8—C9, N2—C7—C8—C10 and N2—C7—C8—C11 torsion angles are 178.6 (4), 57.2 (5) and -59.4 (5) °, respectively. The values of the bond lengths and bond angles in (I) are within the normal range and are comparable to those previously reported for the related structures (Akkurt et al., 2010; Idemudia et al., 2012; Asiri et al., 2012). The crystal structure is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1 and Fig. 2).