N-(2-Chloro­phenyl­sulfon­yl)-2-methyl­propanamide

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

doi:10.1107/S1600536811004284

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o595

doi:10.1107/S1600536811004284

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N-(2-Chlorophenylsulfonyl)-2-methylpropanamide

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 3 February 2011; accepted 4 February 2011; online 9 February 2011)

In the title compound, C₁₀H₁₂ClNO₃S, the amide H atom is syn with respect to the ortho-chloro group in the benzene ring and the C—S—N—C torsion angle is 64.35 (16)°. The benzene ring and the SO₂—NH—CO—C segment form a dihedral angle of 87.4 (1)°. The crystal structure features inversion-related dimers linked by pairs of N—H⋯O hydrogen bonds.

Related literature

For the sulfanilamide moiety in sulfonamide drugs, see; Maren (1976 ). For its ability to form hydrogen bonds in the solid state, see; Yang & Guillory (1972 ). For the hydrogen-bonding characteristics of sulfonamides, see; Adsmond & Grant (2001 ). For the effect of substituents on the crystal structures of sulfonoamides, see: Gowda et al. (2008 , 2009 , 2010 )

Experimental

Crystal data

C₁₀H₁₂ClNO₃S
M_r = 261.72
Triclinic, $[P \overline 1]$
a = 8.365 (1) Å
b = 8.719 (1) Å
c = 9.143 (1) Å
α = 92.74 (1)°
β = 104.22 (1)°
γ = 108.75 (1)°
V = 606.24 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 293 K
0.45 × 0.35 × 0.35 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 = 0.814, T_max = 0.851
4031 measured reflections
2481 independent reflections
2200 reflections with I > 2σ(I)
R_int = 0.011

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.102
S = 1.04
2481 reflections
149 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.84 (2)	2.14 (2)	2.976 (2)	174 (2)
Symmetry code: (i) -x+1, -y, -z.

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/S1600536811004284/ds2091sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004284/ds2091Isup2.hkl

checkCIF report

Comment top

The molecular structures of sulfonamide drugs contain the sulfanilamide moiety (Maren, 1976). The affinity for hydrogen bonding in the solid state due to the presence of various hydrogen bond donors and acceptors can give 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 play a significant role on the crystal structures of N-(aryl)sulfonoamides (Gowda et al., 2008, 2009, 2010). As a part of studying the substituent effects on the structures of this class of compounds, the structure of N-(2-chlorophenylsulfonyl)-2,2-dimethylacetamide (I) has been determined. The conformations of the N—H and C=O bonds of the SO₂—NH—CO—C segment in the structure are anti to each other (Fig. 1), similar to that observed in N-(phenylsulfonyl)-acetamide (II) (Gowda et al., 2010), 2,2-dimethyl-N-(phenylsulfonyl)- acetamide (III)(Gowda et al., 2009) and 2,2-dichloro-N- (phenylsulfonyl)-acetamide (IV) (Gowda et al., 2008).

The molecule in (I) is bent at the S-atom with a C1—S1—N1—C7 torsion angle of 64.4 (2)°, compared to the values of -58.8 (4)° in (II), 67.1 (3)° in (III) and -66.3 (3)° in (IV). Further, the dihedral angle between the benzene ring and the SO2—NH—CO—C group in (I) is 87.4 (1)°, compared to the values of 89.0 (2)° in (II), 87.4 (1)° in (III) and 79.8 (1)° in (IV),

In the crystal structure, the intermolecular N–H···O hydrogen bonds (Table 1) link the molecules through inversion-related dimers into zigzag chains in the bc-plane. Part of the crystal structure is shown in Fig. 2.

Related literature top

For the sulfanilamide moiety in sulfonamide drugs, see; Maren (1976). For its ability to form hydrogen bonds in the solid state, see; Yang & Guillory (1972). For the hydrogen-bonding characteristics of sulfonamides, see; Adsmond & Grant (2001). For the effect of substituents on the crystal structures of sulfonoamides, see: Gowda et al. (2008, 2009, 2010)

Experimental top

The title compound was prepared by refluxing 2-chlorobenzenesulfonamide (0.10 mole) with an excess of 2,2-dimethylacetyl chloride (0.20 mole) for one 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 reprecipitated by acidifying the filtered solution with glacial acetic acid. It was filtered, dried and recrystallized from ethanol. The purity of the compound was checked by determining its melting point. It was further characterized by recording its infrared spectra.

Prism like colorless single crystals 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-methylpropanamide top

Crystal data top

C₁₀H₁₂ClNO₃S	Z = 2
M_r = 261.72	F(000) = 272
Triclinic, P1	D_x = 1.434 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.365 (1) Å	Cell parameters from 2678 reflections
b = 8.719 (1) Å	θ = 3.0–27.7°
c = 9.143 (1) Å	µ = 0.48 mm⁻¹
α = 92.74 (1)°	T = 293 K
β = 104.22 (1)°	Prism, colourless
γ = 108.75 (1)°	0.45 × 0.35 × 0.35 mm
V = 606.24 (12) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2481 independent reflections
Radiation source: fine-focus sealed tube	2200 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.011
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −10→10
T_min = 0.814, T_max = 0.851	k = −10→9
4031 measured reflections	l = −11→11

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) = 0.102	w = 1/[σ²(F_o²) + (0.0589P)² + 0.1796P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2481 reflections	Δρ_max = 0.39 e Å⁻³
149 parameters	Δρ_min = −0.27 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: 0.074 (7)

Crystal data top

C₁₀H₁₂ClNO₃S	γ = 108.75 (1)°
M_r = 261.72	V = 606.24 (12) Å³
Triclinic, P1	Z = 2
a = 8.365 (1) Å	Mo Kα radiation
b = 8.719 (1) Å	µ = 0.48 mm⁻¹
c = 9.143 (1) Å	T = 293 K
α = 92.74 (1)°	0.45 × 0.35 × 0.35 mm
β = 104.22 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2481 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2200 reflections with I > 2σ(I)
T_min = 0.814, T_max = 0.851	R_int = 0.011
4031 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.39 e Å⁻³
2481 reflections	Δρ_min = −0.27 e Å⁻³
149 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	0.8887 (2)	0.33504 (18)	0.17180 (18)	0.0374 (3)
C2	0.9618 (2)	0.2693 (2)	0.07502 (19)	0.0455 (4)
C3	1.1391 (3)	0.3366 (3)	0.0881 (2)	0.0571 (5)
H3	1.1882	0.2924	0.0234	0.069*
C4	1.2436 (3)	0.4688 (3)	0.1967 (3)	0.0581 (5)
H4	1.3630	0.5137	0.2051	0.070*
C5	1.1725 (3)	0.5347 (2)	0.2926 (2)	0.0546 (5)
H5	1.2436	0.6243	0.3656	0.065*
C6	0.9956 (2)	0.4682 (2)	0.2808 (2)	0.0441 (4)
H6	0.9477	0.5128	0.3462	0.053*
C7	0.7107 (2)	0.0482 (2)	0.36475 (18)	0.0397 (4)
C8	0.6623 (2)	−0.1303 (2)	0.3835 (2)	0.0481 (4)
H8	0.5375	−0.1848	0.3306	0.058*
C9	0.6889 (5)	−0.1514 (4)	0.5501 (3)	0.0922 (9)
H9A	0.6168	−0.1053	0.5915	0.111*
H9B	0.8101	−0.0965	0.6046	0.111*
H9C	0.6566	−0.2657	0.5599	0.111*
C10	0.7668 (3)	−0.2058 (3)	0.3089 (3)	0.0720 (6)
H10A	0.8900	−0.1503	0.3556	0.086*
H10B	0.7401	−0.1958	0.2023	0.086*
H10C	0.7368	−0.3194	0.3215	0.086*
Cl1	0.83725 (8)	0.10188 (7)	−0.06290 (7)	0.0749 (2)
N1	0.63339 (19)	0.07529 (16)	0.22009 (16)	0.0418 (3)
H1N	0.578 (3)	−0.005 (2)	0.150 (2)	0.050*
O1	0.55713 (17)	0.22202 (16)	0.00990 (15)	0.0571 (4)
O2	0.63345 (17)	0.36011 (15)	0.27093 (17)	0.0567 (4)
O3	0.8089 (2)	0.16099 (17)	0.46098 (15)	0.0609 (4)
S1	0.66390 (5)	0.25610 (5)	0.16468 (5)	0.04147 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0413 (8)	0.0280 (7)	0.0386 (8)	0.0104 (6)	0.0055 (6)	0.0046 (6)
C2	0.0544 (10)	0.0359 (8)	0.0409 (8)	0.0119 (7)	0.0098 (7)	−0.0009 (7)
C3	0.0622 (12)	0.0528 (11)	0.0604 (11)	0.0176 (9)	0.0277 (10)	0.0037 (9)
C4	0.0452 (10)	0.0501 (11)	0.0717 (13)	0.0050 (8)	0.0189 (9)	0.0054 (9)
C5	0.0481 (10)	0.0384 (9)	0.0610 (11)	0.0013 (8)	0.0072 (8)	−0.0068 (8)
C6	0.0469 (9)	0.0341 (8)	0.0452 (9)	0.0108 (7)	0.0077 (7)	−0.0024 (7)
C7	0.0393 (8)	0.0378 (8)	0.0400 (8)	0.0126 (7)	0.0090 (7)	0.0020 (6)
C8	0.0424 (9)	0.0400 (9)	0.0549 (10)	0.0088 (7)	0.0070 (8)	0.0130 (8)
C9	0.118 (2)	0.0910 (19)	0.0757 (17)	0.0331 (18)	0.0383 (16)	0.0458 (15)
C10	0.0806 (16)	0.0527 (12)	0.0824 (16)	0.0358 (12)	0.0069 (12)	−0.0016 (11)
Cl1	0.0767 (4)	0.0630 (4)	0.0670 (4)	0.0134 (3)	0.0098 (3)	−0.0306 (3)
N1	0.0444 (8)	0.0286 (7)	0.0412 (7)	0.0055 (6)	0.0017 (6)	0.0008 (5)
O1	0.0500 (7)	0.0446 (7)	0.0586 (8)	0.0094 (6)	−0.0090 (6)	0.0123 (6)
O2	0.0506 (7)	0.0399 (7)	0.0824 (10)	0.0184 (6)	0.0210 (7)	0.0004 (6)
O3	0.0738 (9)	0.0465 (7)	0.0459 (7)	0.0160 (7)	−0.0040 (6)	−0.0078 (6)
S1	0.0381 (2)	0.0302 (2)	0.0493 (3)	0.01005 (16)	0.00256 (17)	0.00424 (17)

Geometric parameters (Å, º) top

C1—C6	1.387 (2)	C7—C8	1.507 (2)
C1—C2	1.389 (2)	C8—C10	1.511 (3)
C1—S1	1.7659 (17)	C8—C9	1.514 (3)
C2—C3	1.380 (3)	C8—H8	0.9800
C2—Cl1	1.7344 (18)	C9—H9A	0.9600
C3—C4	1.377 (3)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C4—C5	1.371 (3)	C10—H10A	0.9600
C4—H4	0.9300	C10—H10B	0.9600
C5—C6	1.379 (3)	C10—H10C	0.9600
C5—H5	0.9300	N1—S1	1.6396 (14)
C6—H6	0.9300	N1—H1N	0.843 (15)
C7—O3	1.208 (2)	O1—S1	1.4341 (13)
C7—N1	1.390 (2)	O2—S1	1.4202 (14)

C6—C1—C2	119.32 (16)	C7—C8—H8	108.1
C6—C1—S1	117.57 (13)	C10—C8—H8	108.1
C2—C1—S1	123.11 (13)	C9—C8—H8	108.1
C3—C2—C1	119.91 (16)	C8—C9—H9A	109.5
C3—C2—Cl1	118.08 (14)	C8—C9—H9B	109.5
C1—C2—Cl1	122.01 (14)	H9A—C9—H9B	109.5
C4—C3—C2	120.17 (18)	C8—C9—H9C	109.5
C4—C3—H3	119.9	H9A—C9—H9C	109.5
C2—C3—H3	119.9	H9B—C9—H9C	109.5
C5—C4—C3	120.34 (18)	C8—C10—H10A	109.5
C5—C4—H4	119.8	C8—C10—H10B	109.5
C3—C4—H4	119.8	H10A—C10—H10B	109.5
C4—C5—C6	119.98 (17)	C8—C10—H10C	109.5
C4—C5—H5	120.0	H10A—C10—H10C	109.5
C6—C5—H5	120.0	H10B—C10—H10C	109.5
C5—C6—C1	120.28 (17)	C7—N1—S1	124.59 (11)
C5—C6—H6	119.9	C7—N1—H1N	119.7 (15)
C1—C6—H6	119.9	S1—N1—H1N	115.1 (14)
O3—C7—N1	120.87 (16)	O2—S1—O1	118.79 (9)
O3—C7—C8	125.77 (16)	O2—S1—N1	109.66 (8)
N1—C7—C8	113.34 (14)	O1—S1—N1	104.14 (8)
C7—C8—C10	109.40 (16)	O2—S1—C1	107.71 (8)
C7—C8—C9	110.55 (18)	O1—S1—C1	110.42 (8)
C10—C8—C9	112.5 (2)	N1—S1—C1	105.30 (8)

C6—C1—C2—C3	0.1 (3)	O3—C7—C8—C9	23.2 (3)
S1—C1—C2—C3	−179.39 (15)	N1—C7—C8—C9	−158.19 (19)
C6—C1—C2—Cl1	179.41 (13)	O3—C7—N1—S1	−0.2 (2)
S1—C1—C2—Cl1	0.0 (2)	C8—C7—N1—S1	−178.89 (12)
C1—C2—C3—C4	−0.1 (3)	C7—N1—S1—O2	−51.29 (16)
Cl1—C2—C3—C4	−179.50 (16)	C7—N1—S1—O1	−179.42 (14)
C2—C3—C4—C5	0.0 (3)	C7—N1—S1—C1	64.35 (16)
C3—C4—C5—C6	0.2 (3)	C6—C1—S1—O2	4.95 (16)
C4—C5—C6—C1	−0.3 (3)	C2—C1—S1—O2	−175.59 (14)
C2—C1—C6—C5	0.1 (3)	C6—C1—S1—O1	136.13 (13)
S1—C1—C6—C5	179.61 (14)	C2—C1—S1—O1	−44.41 (16)
O3—C7—C8—C10	−101.1 (2)	C6—C1—S1—N1	−112.02 (14)
N1—C7—C8—C10	77.45 (19)	C2—C1—S1—N1	67.44 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.84 (2)	2.14 (2)	2.976 (2)	174 (2)

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂ClNO₃S
M_r	261.72
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.365 (1), 8.719 (1), 9.143 (1)
α, β, γ (°)	92.74 (1), 104.22 (1), 108.75 (1)
V (Å³)	606.24 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.45 × 0.35 × 0.35

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	0.814, 0.851
No. of measured, independent and observed [I > 2σ(I)] reflections	4031, 2481, 2200
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.102, 1.04
No. of reflections	2481
No. of parameters	149
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)	0.39, −0.27

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	0.843 (15)	2.136 (16)	2.976 (2)	174 (2)

Symmetry code: (i) −x+1, −y, −z.

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

Adsmond, D. A. & Grant, D. J. W. (2001). J. Pharm. Sci. 90, 2058–2077. Web of Science CrossRef PubMed CAS Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2009). Acta Cryst. E65, o2680. Web of Science CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o1284. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o1522. Web of Science CSD CrossRef IUCr Journals Google Scholar
Maren, T. H. (1976). Annu. Rev. Pharmacol Toxicol. 16, 309–327. CrossRef CAS PubMed Web of Science Google Scholar
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England. 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
Yang, S. S. & Guillory, J. K. (1972). J. Pharm. Sci. 61, 26–40. CrossRef CAS PubMed Web of Science Google Scholar