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

Shakuntala, K.; Foro, S.; Gowda, B.T.

doi:10.1107/S1600536811017429

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1400

doi:10.1107/S1600536811017429

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

K. Shakuntala,^a Sabine Foro ^b and B. Thimme Gowda ^a ^*

^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 ). 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

Crystal data

C₁₁H₁₄ClNO₃S
M_r = 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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.831, T_max = 0.852
4355 measured reflections
2730 independent reflections
2321 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017429/tk2742sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017429/tk2742Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017429/tk2742Isup3.cml

checkCIF report

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 C═O 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 S═O 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.

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

	Fig. 1. Molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	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

C₁₁H₁₄ClNO₃S	Z = 2
M_r = 275.74	F(000) = 288
Triclinic, P1	D_x = 1.365 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.785 (1) Å	Cell parameters from 2522 reflections
b = 8.914 (1) Å	θ = 3.1–27.7°
c = 9.313 (1) Å	µ = 0.44 mm⁻¹
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 tube	2321 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
Rotation method data acquisition using ω and ϕ scans	θ_max = 26.4°, θ_min = 3.2°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→10
T_min = 0.831, T_max = 0.852	k = −11→10
4355 measured reflections	l = −11→7

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0533P)² + 0.2343P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.004
2730 reflections	Δρ_max = 0.26 e Å⁻³
158 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.129 (8)

Crystal data top

C₁₁H₁₄ClNO₃S	γ = 94.20 (1)°
M_r = 275.74	V = 670.98 (13) Å³
Triclinic, P1	Z = 2
a = 8.785 (1) Å	Mo Kα radiation
b = 8.914 (1) Å	µ = 0.44 mm⁻¹
c = 9.313 (1) Å	T = 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)
T_min = 0.831, T_max = 0.852	R_int = 0.012
4355 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.26 e Å⁻³
2730 reflections	Δρ_min = −0.26 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	0.1873 (2)	0.8220 (2)	0.6448 (2)	0.0421 (4)
C2	0.2567 (2)	0.9285 (2)	0.5857 (2)	0.0506 (5)
C3	0.1853 (3)	0.9346 (3)	0.4339 (3)	0.0635 (6)
H3	0.2316	1.0059	0.3940	0.076*
C4	0.0468 (3)	0.8358 (3)	0.3420 (3)	0.0666 (6)
H4	−0.0012	0.8417	0.2405	0.080*
C5	−0.0218 (2)	0.7287 (3)	0.3977 (3)	0.0603 (5)
H5	−0.1153	0.6614	0.3341	0.072*
C6	0.0485 (2)	0.7210 (2)	0.5489 (2)	0.0482 (4)
H6	0.0026	0.6476	0.5868	0.058*
C7	0.4718 (2)	0.6231 (2)	0.7753 (2)	0.0424 (4)
C8	0.6484 (2)	0.6029 (2)	0.8078 (2)	0.0473 (4)
C9	0.7309 (3)	0.7253 (3)	0.7535 (4)	0.0773 (7)
H9A	0.7220	0.8274	0.8089	0.093*
H9B	0.6802	0.7112	0.6439	0.093*
H9C	0.8427	0.7144	0.7735	0.093*
C10	0.7287 (3)	0.6256 (4)	0.9819 (3)	0.0817 (8)
H10A	0.6750	0.5503	1.0166	0.098*
H10B	0.7221	0.7287	1.0368	0.098*
H10C	0.8398	0.6122	1.0018	0.098*
C11	0.6588 (3)	0.4422 (3)	0.7175 (4)	0.0894 (9)
H11A	0.6088	0.4308	0.6082	0.107*
H11B	0.6044	0.3650	0.7496	0.107*
H11C	0.7699	0.4287	0.7373	0.107*
N1	0.44486 (18)	0.76248 (19)	0.86001 (19)	0.0483 (4)
H1N	0.515 (2)	0.838 (2)	0.912 (2)	0.058*
O1	0.29358 (17)	0.96456 (19)	0.94151 (18)	0.0656 (4)
O2	0.16258 (17)	0.69277 (19)	0.86012 (18)	0.0635 (4)
O3	0.36032 (17)	0.52985 (17)	0.68368 (18)	0.0614 (4)
Cl1	0.43167 (8)	1.05545 (7)	0.69656 (9)	0.0820 (2)
S1	0.26460 (5)	0.81187 (6)	0.83971 (5)	0.04740 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0325 (8)	0.0377 (8)	0.0535 (10)	0.0082 (6)	0.0111 (7)	0.0092 (7)
C2	0.0415 (9)	0.0402 (9)	0.0667 (12)	0.0038 (7)	0.0138 (9)	0.0127 (8)
C3	0.0661 (14)	0.0577 (12)	0.0771 (15)	0.0134 (10)	0.0264 (12)	0.0318 (11)
C4	0.0639 (13)	0.0745 (15)	0.0584 (13)	0.0198 (12)	0.0086 (10)	0.0229 (11)
C5	0.0428 (10)	0.0636 (13)	0.0600 (12)	0.0055 (9)	0.0030 (9)	0.0062 (10)
C6	0.0353 (9)	0.0434 (9)	0.0613 (11)	0.0039 (7)	0.0132 (8)	0.0082 (8)
C7	0.0408 (9)	0.0427 (9)	0.0450 (9)	0.0069 (7)	0.0136 (7)	0.0142 (7)
C8	0.0415 (9)	0.0493 (10)	0.0518 (10)	0.0140 (8)	0.0151 (8)	0.0119 (8)
C9	0.0606 (14)	0.0830 (17)	0.104 (2)	0.0109 (12)	0.0483 (14)	0.0255 (15)
C10	0.0679 (15)	0.109 (2)	0.0668 (15)	0.0413 (15)	0.0077 (12)	0.0302 (14)
C11	0.0721 (16)	0.0639 (15)	0.118 (2)	0.0272 (13)	0.0259 (16)	−0.0034 (15)
N1	0.0327 (8)	0.0500 (9)	0.0538 (9)	0.0090 (6)	0.0079 (6)	0.0042 (7)
O1	0.0498 (8)	0.0707 (10)	0.0623 (9)	0.0196 (7)	0.0132 (7)	−0.0068 (7)
O2	0.0460 (8)	0.0832 (11)	0.0725 (10)	0.0109 (7)	0.0249 (7)	0.0343 (8)
O3	0.0470 (8)	0.0519 (8)	0.0717 (9)	−0.0013 (6)	0.0117 (7)	0.0019 (7)
Cl1	0.0639 (4)	0.0658 (4)	0.1008 (5)	−0.0238 (3)	0.0154 (3)	0.0167 (3)
S1	0.0350 (2)	0.0546 (3)	0.0507 (3)	0.01154 (19)	0.01324 (19)	0.0089 (2)

Geometric parameters (Å, º) top

C1—C6	1.389 (2)	C8—C9	1.524 (3)
C1—C2	1.388 (3)	C8—C10	1.524 (3)
C1—S1	1.7664 (19)	C9—H9A	0.9600
C2—C3	1.383 (3)	C9—H9B	0.9600
C2—Cl1	1.728 (2)	C9—H9C	0.9600
C3—C4	1.370 (3)	C10—H10A	0.9600
C3—H3	0.9300	C10—H10B	0.9600
C4—C5	1.368 (3)	C10—H10C	0.9600
C4—H4	0.9300	C11—H11A	0.9600
C5—C6	1.381 (3)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C6—H6	0.9300	N1—S1	1.6434 (15)
C7—O3	1.202 (2)	N1—H1N	0.826 (16)
C7—N1	1.389 (2)	O1—S1	1.4274 (15)
C7—C8	1.523 (2)	O2—S1	1.4209 (16)
C8—C11	1.512 (3)

C6—C1—C2	119.18 (18)	C8—C9—H9A	109.5
C6—C1—S1	117.88 (15)	C8—C9—H9B	109.5
C2—C1—S1	122.92 (14)	H9A—C9—H9B	109.5
C3—C2—C1	119.74 (18)	C8—C9—H9C	109.5
C3—C2—Cl1	118.34 (16)	H9A—C9—H9C	109.5
C1—C2—Cl1	121.92 (16)	H9B—C9—H9C	109.5
C4—C3—C2	120.2 (2)	C8—C10—H10A	109.5
C4—C3—H3	119.9	C8—C10—H10B	109.5
C2—C3—H3	119.9	H10A—C10—H10B	109.5
C5—C4—C3	120.8 (2)	C8—C10—H10C	109.5
C5—C4—H4	119.6	H10A—C10—H10C	109.5
C3—C4—H4	119.6	H10B—C10—H10C	109.5
C4—C5—C6	119.62 (19)	C8—C11—H11A	109.5
C4—C5—H5	120.2	C8—C11—H11B	109.5
C6—C5—H5	120.2	H11A—C11—H11B	109.5
C5—C6—C1	120.45 (19)	C8—C11—H11C	109.5
C5—C6—H6	119.8	H11A—C11—H11C	109.5
C1—C6—H6	119.8	H11B—C11—H11C	109.5
O3—C7—N1	120.27 (17)	C7—N1—S1	123.31 (13)
O3—C7—C8	124.89 (17)	C7—N1—H1N	125.0 (16)
N1—C7—C8	114.84 (15)	S1—N1—H1N	110.5 (16)
C11—C8—C7	109.01 (18)	O2—S1—O1	118.83 (10)
C11—C8—C9	109.4 (2)	O2—S1—N1	109.93 (9)
C7—C8—C9	108.39 (16)	O1—S1—N1	104.49 (9)
C11—C8—C10	110.8 (2)	O2—S1—C1	107.67 (9)
C7—C8—C10	109.76 (17)	O1—S1—C1	109.39 (9)
C9—C8—C10	109.4 (2)	N1—S1—C1	105.81 (8)

C6—C1—C2—C3	1.3 (3)	N1—C7—C8—C9	−65.3 (2)
S1—C1—C2—C3	−177.01 (16)	O3—C7—C8—C10	−126.5 (2)
C6—C1—C2—Cl1	−178.68 (14)	N1—C7—C8—C10	54.2 (2)
S1—C1—C2—Cl1	3.0 (2)	O3—C7—N1—S1	−1.5 (3)
C1—C2—C3—C4	−0.1 (3)	C8—C7—N1—S1	177.89 (13)
Cl1—C2—C3—C4	179.88 (18)	C7—N1—S1—O2	54.30 (18)
C2—C3—C4—C5	−0.9 (4)	C7—N1—S1—O1	−177.13 (15)
C3—C4—C5—C6	0.6 (3)	C7—N1—S1—C1	−61.69 (17)
C4—C5—C6—C1	0.6 (3)	C6—C1—S1—O2	0.55 (16)
C2—C1—C6—C5	−1.5 (3)	C2—C1—S1—O2	178.86 (15)
S1—C1—C6—C5	176.85 (15)	C6—C1—S1—O1	−129.89 (14)
O3—C7—C8—C11	−4.9 (3)	C2—C1—S1—O1	48.42 (17)
N1—C7—C8—C11	175.7 (2)	C6—C1—S1—N1	118.06 (15)
O3—C7—C8—C9	114.0 (2)	C2—C1—S1—N1	−63.63 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄ClNO₃S
M_r	275.74
Crystal system, space group	Triclinic, 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)
V (Å³)	670.98 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.44 × 0.40 × 0.38

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.831, 0.852
No. of measured, independent and observed [I > 2σ(I)] reflections	4355, 2730, 2321
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.107, 1.06
No. of reflections	2730
No. of parameters	158
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.826 (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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