organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-(2-Chloro­phenyl­sulfon­yl)-2,2-di­methyl­propanamide

aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com

(Received 5 May 2011; accepted 9 May 2011; online 14 May 2011)

In the title compound, C11H14ClNO3S, the C—S—N—C torsion angle is −61.69 (17)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur, generating R22(8) loops.

Related literature

For the sulfanilamide moiety in sulfonamide drugs, see: Maren (1976[Maren, T. H. (1976). Annu. Rev. Pharmacol Toxicol. 16, 309-327.]). For the ability of sulfonamides to form hydrogen bonds in the solid state, see: Yang & Guillory (1972[Yang, S. S. & Guillory, J. K. (1972). J. Pharm. Sci. 61, 26-40.]). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001[Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058-2077.]). For our study of the effect of substituents on the structures of N-(ar­yl)-methane­sulfonamides, see: Gowda et al. (2007[Gowda, B. T., Foro, S. & Fuess, H. (2007). Acta Cryst. E63, o2597.]). For related structures, see: Gowda et al. (2008[Gowda, B. T., Foro, S., Sowmya, B. P., Nirmala, P. G. & Fuess, H. (2008). Acta Cryst. E64, o1410.]); Shakuntala et al. (2011a[Shakuntala, K., Foro, S. & Gowda, B. T. (2011a). Acta Cryst. E67, o549.],b[Shakuntala, K., Foro, S. & Gowda, B. T. (2011b). Acta Cryst. E67, o1097.]).

[Scheme 1]

Experimental

Crystal data
  • C11H14ClNO3S

  • Mr = 275.74

  • Triclinic, [P \overline 1]

  • a = 8.785 (1) Å

  • b = 8.914 (1) Å

  • c = 9.313 (1) Å

  • α = 103.12 (1)°

  • β = 107.14 (1)°

  • γ = 94.20 (1)°

  • V = 670.98 (13) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.44 mm−1

  • T = 293 K

  • 0.44 × 0.40 × 0.38 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.831, Tmax = 0.852

  • 4355 measured reflections

  • 2730 independent reflections

  • 2321 reflections with I > 2σ(I)

  • Rint = 0.012

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.107

  • S = 1.06

  • 2730 reflections

  • 158 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O1i 0.83 (2) 2.22 (2) 3.042 (2) 178 (2)
Symmetry code: (i) -x+1, -y+2, -z+2.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The molecular structures of sulfonamide drugs contain the sulfanilamide moiety (Maren, 1976). The propensity for hydrogen bonding in the solid state, due to the presence of various hydrogen bond donors and acceptors, gives rise to polymorphism (Yang & Guillory, 1972). The hydrogen bonding preferences of sulfonamides has also been investigated (Adsmond & Grant, 2001). The nature and position of substituents in N-(aryl)sulfonoamides play a significant role on their crystal structures. As a part of a study of the substituent effects upon their crystal structures (Gowda et al., 2007, 2008; Shakuntala et al., 2011a,b), in the present work, the crystal structure of N-(2-chlorophenylsulfonyl)-2,2,2-trimethylacetamide (I) has been determined. The N—H and CO bonds in the SO2—NH—CO—C segment of (I) are anti to each other (Fig. 1), similar to that observed in N-(2-methylphenylsulfonyl)-2,2,2- trimethylacetamide (II) (Shakuntala et al., 2011a), N-(phenylsulfonyl)-2,2,2-trimethylacetamide (III) (Gowda et al., 2008) and N-(2-chlorophenylsulfonyl)-acetamide (IV) (Shakuntala et al., 2011b). Further, the amide hydrogen is syn to the ortho-chloro group in the benzene ring.

The N—C bond in the C—SO2—NH—C segment has gauche torsion with respect to the SO bonds. The molecule is twisted at the S- atom with a C—S—N—C torsion angle of -61.7 (2) °, compared to the values of -65.4 (2) ° in (II), -64.5 (3) ° in (III), and -71.7 (3) ° and 61.2 (3) ° in the two independent molecules of (IV).

In the crystal structure, the pairs of intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into inversion-related dimers; a view of the crystal packing is shown in Fig. 2.

Related literature top

For the sulfanilamide moiety in sulfonamide drugs, see: Maren (1976). For the ability of sulfonamides to form hydrogen bonds in the solid state, see: Yang & Guillory (1972). For hydrogen-bonding modes of sulfonamides, see: Adsmond & Grant (2001). For our study of the effect of substituents on the structures of N-(aryl)-methanesulfonamides, see: Gowda et al. (2007). For related structures, see: Gowda et al. (2008); Shakuntala et al. (2011a,b).

Experimental top

The title compound was prepared by refluxing 2-chlorobenzenesulfonamide (0.10 mole) with an excess of pivalyl chloride (0.20 mole) for about an hour on a water bath. The reaction mixture was cooled and poured into ice cold water. The resulting solid was separated, washed thoroughly with water and dissolved in warm dilute sodium hydrogen carbonate solution. The title compound was re-precipitated by acidifying the filtered solution with glacial acetic acid. It was filtered, dried and recrystallized from ethanol. Colorless prisms of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of an ethanolic solution of the compound.

Refinement top

The H atom of the NH group was located in a difference map and later restrained to the distance N—H = 0.86 (2) Å The other H atoms were positioned with idealized geometry using a riding model with the aromatic C—H = 0.93 Å and methyl C—H = 0.96 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines.
N-(2-Chlorophenylsulfonyl)-2,2-dimethylpropanamide top
Crystal data top
C11H14ClNO3SZ = 2
Mr = 275.74F(000) = 288
Triclinic, P1Dx = 1.365 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.785 (1) ÅCell parameters from 2522 reflections
b = 8.914 (1) Åθ = 3.1–27.7°
c = 9.313 (1) ŵ = 0.44 mm1
α = 103.12 (1)°T = 293 K
β = 107.14 (1)°Prism, colourless
γ = 94.20 (1)°0.44 × 0.40 × 0.38 mm
V = 670.98 (13) Å3
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2730 independent reflections
Radiation source: fine-focus sealed tube2321 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
Rotation method data acquisition using ω and ϕ scansθmax = 26.4°, θmin = 3.2°
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
h = 1010
Tmin = 0.831, Tmax = 0.852k = 1110
4355 measured reflectionsl = 117
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0533P)2 + 0.2343P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.004
2730 reflectionsΔρmax = 0.26 e Å3
158 parametersΔρmin = 0.26 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.129 (8)
Crystal data top
C11H14ClNO3Sγ = 94.20 (1)°
Mr = 275.74V = 670.98 (13) Å3
Triclinic, P1Z = 2
a = 8.785 (1) ÅMo Kα radiation
b = 8.914 (1) ŵ = 0.44 mm1
c = 9.313 (1) ÅT = 293 K
α = 103.12 (1)°0.44 × 0.40 × 0.38 mm
β = 107.14 (1)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
2730 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)
2321 reflections with I > 2σ(I)
Tmin = 0.831, Tmax = 0.852Rint = 0.012
4355 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0361 restraint
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.26 e Å3
2730 reflectionsΔρmin = 0.26 e Å3
158 parameters
Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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) top
xyzUiso*/Ueq
C10.1873 (2)0.8220 (2)0.6448 (2)0.0421 (4)
C20.2567 (2)0.9285 (2)0.5857 (2)0.0506 (5)
C30.1853 (3)0.9346 (3)0.4339 (3)0.0635 (6)
H30.23161.00590.39400.076*
C40.0468 (3)0.8358 (3)0.3420 (3)0.0666 (6)
H40.00120.84170.24050.080*
C50.0218 (2)0.7287 (3)0.3977 (3)0.0603 (5)
H50.11530.66140.33410.072*
C60.0485 (2)0.7210 (2)0.5489 (2)0.0482 (4)
H60.00260.64760.58680.058*
C70.4718 (2)0.6231 (2)0.7753 (2)0.0424 (4)
C80.6484 (2)0.6029 (2)0.8078 (2)0.0473 (4)
C90.7309 (3)0.7253 (3)0.7535 (4)0.0773 (7)
H9A0.72200.82740.80890.093*
H9B0.68020.71120.64390.093*
H9C0.84270.71440.77350.093*
C100.7287 (3)0.6256 (4)0.9819 (3)0.0817 (8)
H10A0.67500.55031.01660.098*
H10B0.72210.72871.03680.098*
H10C0.83980.61221.00180.098*
C110.6588 (3)0.4422 (3)0.7175 (4)0.0894 (9)
H11A0.60880.43080.60820.107*
H11B0.60440.36500.74960.107*
H11C0.76990.42870.73730.107*
N10.44486 (18)0.76248 (19)0.86001 (19)0.0483 (4)
H1N0.515 (2)0.838 (2)0.912 (2)0.058*
O10.29358 (17)0.96456 (19)0.94151 (18)0.0656 (4)
O20.16258 (17)0.69277 (19)0.86012 (18)0.0635 (4)
O30.36032 (17)0.52985 (17)0.68368 (18)0.0614 (4)
Cl10.43167 (8)1.05545 (7)0.69656 (9)0.0820 (2)
S10.26460 (5)0.81187 (6)0.83971 (5)0.04740 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0325 (8)0.0377 (8)0.0535 (10)0.0082 (6)0.0111 (7)0.0092 (7)
C20.0415 (9)0.0402 (9)0.0667 (12)0.0038 (7)0.0138 (9)0.0127 (8)
C30.0661 (14)0.0577 (12)0.0771 (15)0.0134 (10)0.0264 (12)0.0318 (11)
C40.0639 (13)0.0745 (15)0.0584 (13)0.0198 (12)0.0086 (10)0.0229 (11)
C50.0428 (10)0.0636 (13)0.0600 (12)0.0055 (9)0.0030 (9)0.0062 (10)
C60.0353 (9)0.0434 (9)0.0613 (11)0.0039 (7)0.0132 (8)0.0082 (8)
C70.0408 (9)0.0427 (9)0.0450 (9)0.0069 (7)0.0136 (7)0.0142 (7)
C80.0415 (9)0.0493 (10)0.0518 (10)0.0140 (8)0.0151 (8)0.0119 (8)
C90.0606 (14)0.0830 (17)0.104 (2)0.0109 (12)0.0483 (14)0.0255 (15)
C100.0679 (15)0.109 (2)0.0668 (15)0.0413 (15)0.0077 (12)0.0302 (14)
C110.0721 (16)0.0639 (15)0.118 (2)0.0272 (13)0.0259 (16)0.0034 (15)
N10.0327 (8)0.0500 (9)0.0538 (9)0.0090 (6)0.0079 (6)0.0042 (7)
O10.0498 (8)0.0707 (10)0.0623 (9)0.0196 (7)0.0132 (7)0.0068 (7)
O20.0460 (8)0.0832 (11)0.0725 (10)0.0109 (7)0.0249 (7)0.0343 (8)
O30.0470 (8)0.0519 (8)0.0717 (9)0.0013 (6)0.0117 (7)0.0019 (7)
Cl10.0639 (4)0.0658 (4)0.1008 (5)0.0238 (3)0.0154 (3)0.0167 (3)
S10.0350 (2)0.0546 (3)0.0507 (3)0.01154 (19)0.01324 (19)0.0089 (2)
Geometric parameters (Å, º) top
C1—C61.389 (2)C8—C91.524 (3)
C1—C21.388 (3)C8—C101.524 (3)
C1—S11.7664 (19)C9—H9A0.9600
C2—C31.383 (3)C9—H9B0.9600
C2—Cl11.728 (2)C9—H9C0.9600
C3—C41.370 (3)C10—H10A0.9600
C3—H30.9300C10—H10B0.9600
C4—C51.368 (3)C10—H10C0.9600
C4—H40.9300C11—H11A0.9600
C5—C61.381 (3)C11—H11B0.9600
C5—H50.9300C11—H11C0.9600
C6—H60.9300N1—S11.6434 (15)
C7—O31.202 (2)N1—H1N0.826 (16)
C7—N11.389 (2)O1—S11.4274 (15)
C7—C81.523 (2)O2—S11.4209 (16)
C8—C111.512 (3)
C6—C1—C2119.18 (18)C8—C9—H9A109.5
C6—C1—S1117.88 (15)C8—C9—H9B109.5
C2—C1—S1122.92 (14)H9A—C9—H9B109.5
C3—C2—C1119.74 (18)C8—C9—H9C109.5
C3—C2—Cl1118.34 (16)H9A—C9—H9C109.5
C1—C2—Cl1121.92 (16)H9B—C9—H9C109.5
C4—C3—C2120.2 (2)C8—C10—H10A109.5
C4—C3—H3119.9C8—C10—H10B109.5
C2—C3—H3119.9H10A—C10—H10B109.5
C5—C4—C3120.8 (2)C8—C10—H10C109.5
C5—C4—H4119.6H10A—C10—H10C109.5
C3—C4—H4119.6H10B—C10—H10C109.5
C4—C5—C6119.62 (19)C8—C11—H11A109.5
C4—C5—H5120.2C8—C11—H11B109.5
C6—C5—H5120.2H11A—C11—H11B109.5
C5—C6—C1120.45 (19)C8—C11—H11C109.5
C5—C6—H6119.8H11A—C11—H11C109.5
C1—C6—H6119.8H11B—C11—H11C109.5
O3—C7—N1120.27 (17)C7—N1—S1123.31 (13)
O3—C7—C8124.89 (17)C7—N1—H1N125.0 (16)
N1—C7—C8114.84 (15)S1—N1—H1N110.5 (16)
C11—C8—C7109.01 (18)O2—S1—O1118.83 (10)
C11—C8—C9109.4 (2)O2—S1—N1109.93 (9)
C7—C8—C9108.39 (16)O1—S1—N1104.49 (9)
C11—C8—C10110.8 (2)O2—S1—C1107.67 (9)
C7—C8—C10109.76 (17)O1—S1—C1109.39 (9)
C9—C8—C10109.4 (2)N1—S1—C1105.81 (8)
C6—C1—C2—C31.3 (3)N1—C7—C8—C965.3 (2)
S1—C1—C2—C3177.01 (16)O3—C7—C8—C10126.5 (2)
C6—C1—C2—Cl1178.68 (14)N1—C7—C8—C1054.2 (2)
S1—C1—C2—Cl13.0 (2)O3—C7—N1—S11.5 (3)
C1—C2—C3—C40.1 (3)C8—C7—N1—S1177.89 (13)
Cl1—C2—C3—C4179.88 (18)C7—N1—S1—O254.30 (18)
C2—C3—C4—C50.9 (4)C7—N1—S1—O1177.13 (15)
C3—C4—C5—C60.6 (3)C7—N1—S1—C161.69 (17)
C4—C5—C6—C10.6 (3)C6—C1—S1—O20.55 (16)
C2—C1—C6—C51.5 (3)C2—C1—S1—O2178.86 (15)
S1—C1—C6—C5176.85 (15)C6—C1—S1—O1129.89 (14)
O3—C7—C8—C114.9 (3)C2—C1—S1—O148.42 (17)
N1—C7—C8—C11175.7 (2)C6—C1—S1—N1118.06 (15)
O3—C7—C8—C9114.0 (2)C2—C1—S1—N163.63 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.83 (2)2.22 (2)3.042 (2)178 (2)
Symmetry code: (i) x+1, y+2, z+2.

Experimental details

Crystal data
Chemical formulaC11H14ClNO3S
Mr275.74
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.785 (1), 8.914 (1), 9.313 (1)
α, β, γ (°)103.12 (1), 107.14 (1), 94.20 (1)
V3)670.98 (13)
Z2
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.44 × 0.40 × 0.38
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire CCD detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.831, 0.852
No. of measured, independent and
observed [I > 2σ(I)] reflections
4355, 2730, 2321
Rint0.012
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.107, 1.06
No. of reflections2730
No. of parameters158
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.26, 0.26

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1i0.826 (16)2.217 (16)3.042 (2)178 (2)
Symmetry code: (i) x+1, y+2, z+2.
 

Acknowledgements

KS thanks the University Grants Commission, Government of India, New Delhi, for the award of a research fellowship under its faculty improvement program.

References

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