2,2-Dimethyl-N-(phenyl-sulfon-yl)acetamide.

In the title compound, C(10)H(13)NO(3)S, the N-H and C=O bonds in the SO(2)-NH-CO-C segment are anti to each other. The benzene ring and the SO(2)-NH-CO-C segment form a dihedral angle of 87.4 (1)°. The crystal packing features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds.

Related literature

For sulfonamide drugs, see: Maren (1976 ▶). It has been postulated that the propensity for hydrogen bonding in the solid state can give rise to polymorphism due to the presence of various hydrogen-bond donors and acceptors, see: Yang & Guillory (1972 ▶). The hydrogen bonding preferences of sulfon­amides have also been investigated, see: Adsmond & Grant (2001 ▶). The nature and position of substituents play a significant role in the crystal structures of N-(ar­yl)sulfonoamides, see: Gowda et al. (2008a ▶,b ▶,c ▶);

Experimental

Crystal data

C10H13NO3S

M = 227.27

Monoclinic,

a = 6.1240 (4) Å

b = 22.201 (2) Å

c = 8.9192 (9) Å

β = 106.903 (6)°

V = 1160.26 (17) Å3

Z = 4

Cu Kα radiation

μ = 2.40 mm−1

T = 299 K

0.50 × 0.13 × 0.08 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2732 measured reflections

2075 independent reflections

1755 reflections with I > 2σ(I)

R int = 0.047

3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.213

S = 1.08

2075 reflections

140 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.78 e Å−3

Δρmin = −0.58 e Å−3

Data collection: CAD-4-PC (Enraf–Nonius, 1996 ▶); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809040483/fl2270sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809040483/fl2270Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H13NO3S	F(000) = 480
Mr = 227.27	Dx = 1.301 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 6.1240 (4) Å	θ = 4.0–20.3°
b = 22.201 (2) Å	µ = 2.40 mm−1
c = 8.9192 (9) Å	T = 299 K
β = 106.903 (6)°	Rod, colourless
V = 1160.26 (17) Å3	0.50 × 0.13 × 0.08 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.047
Radiation source: fine-focus sealed tube	θmax = 67.0°, θmin = 4.0°
graphite	h = 0→7
ω/2θ scans	k = −26→4
2732 measured reflections	l = −10→10
2075 independent reflections	3 standard reflections every 120 min
1755 reflections with I > 2σ(I)	intensity decay: 1.0%

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)] = 0.073	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.213	w = 1/[σ2(Fo2) + (0.1492P)2 + 0.3098P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2075 reflections	Δρmax = 0.78 e Å−3
140 parameters	Δρmin = −0.58 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (4)

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.

	x	y	z	Uiso*/Ueq
C1	0.4133 (5)	0.36281 (13)	0.1597 (3)	0.0566 (7)
C2	0.6038 (6)	0.3479 (2)	0.1164 (5)	0.0806 (10)
H2	0.6706	0.3751	0.0637	0.097*
C3	0.6932 (8)	0.2901 (3)	0.1549 (7)	0.1103 (19)
H3	0.8212	0.2782	0.1263	0.132*
C4	0.5957 (12)	0.2509 (2)	0.2337 (7)	0.117 (2)
H4	0.6587	0.2128	0.2591	0.141*
C5	0.4070 (11)	0.26677 (19)	0.2757 (6)	0.1049 (15)
H5	0.3418	0.2397	0.3297	0.126*
C6	0.3138 (7)	0.32271 (16)	0.2382 (4)	0.0734 (9)
H6	0.1838	0.3337	0.2655	0.088*
C7	0.0475 (5)	0.41022 (15)	−0.1737 (4)	0.0627 (8)
C8	0.0133 (7)	0.42667 (17)	−0.3429 (4)	0.0721 (9)
H8	0.0582	0.4689	−0.3459	0.087*
C9	0.1661 (13)	0.3903 (4)	−0.4061 (7)	0.162 (3)
H9A	0.1324	0.3484	−0.3988	0.194*
H9B	0.3216	0.3980	−0.3470	0.194*
H9C	0.1443	0.4008	−0.5139	0.194*
C10	−0.2332 (10)	0.4217 (3)	−0.4352 (6)	0.123 (2)
H10A	−0.3227	0.4479	−0.3908	0.148*
H10B	−0.2835	0.3809	−0.4321	0.148*
H10C	−0.2514	0.4332	−0.5420	0.148*
N1	0.2199 (5)	0.44210 (13)	−0.0704 (3)	0.0632 (8)
H1N	0.280 (7)	0.4703 (19)	−0.101 (5)	0.076*
O1	0.1032 (5)	0.43906 (11)	0.1775 (3)	0.0754 (7)
O2	0.4768 (5)	0.47818 (11)	0.1727 (3)	0.0779 (8)
O3	−0.0530 (5)	0.37102 (14)	−0.1283 (3)	0.0923 (10)
S1	0.29657 (13)	0.43493 (3)	0.12050 (8)	0.0570 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0624 (17)	0.0556 (16)	0.0489 (15)	−0.0002 (12)	0.0118 (13)	−0.0021 (11)
C2	0.0643 (19)	0.094 (3)	0.084 (2)	−0.0031 (18)	0.0227 (17)	−0.020 (2)
C3	0.074 (3)	0.120 (4)	0.122 (4)	0.030 (3)	0.005 (3)	−0.043 (3)
C4	0.137 (5)	0.080 (3)	0.105 (4)	0.038 (3)	−0.012 (3)	−0.005 (3)
C5	0.144 (4)	0.071 (2)	0.094 (3)	0.014 (3)	0.026 (3)	0.021 (2)
C6	0.090 (2)	0.0648 (19)	0.0673 (19)	0.0021 (17)	0.0261 (17)	0.0103 (15)
C7	0.0627 (17)	0.0669 (18)	0.0547 (17)	−0.0113 (14)	0.0112 (14)	0.0026 (13)
C8	0.083 (2)	0.076 (2)	0.0534 (18)	−0.0139 (17)	0.0147 (16)	−0.0006 (15)
C9	0.184 (7)	0.226 (8)	0.096 (4)	0.083 (6)	0.074 (4)	0.015 (5)
C10	0.113 (4)	0.163 (5)	0.068 (3)	−0.016 (3)	−0.015 (3)	0.003 (3)
N1	0.0731 (17)	0.0619 (16)	0.0497 (14)	−0.0170 (12)	0.0104 (12)	0.0071 (11)
O1	0.0876 (17)	0.0760 (16)	0.0715 (15)	0.0129 (12)	0.0370 (13)	0.0004 (11)
O2	0.0986 (18)	0.0689 (14)	0.0570 (13)	−0.0292 (12)	0.0081 (12)	−0.0041 (10)
O3	0.0977 (19)	0.108 (2)	0.0663 (15)	−0.0501 (16)	0.0162 (13)	0.0048 (13)
S1	0.0701 (6)	0.0519 (5)	0.0477 (5)	−0.0063 (3)	0.0153 (4)	−0.0007 (3)

C1—C2	1.372 (5)	C7—C8	1.507 (4)
C1—C6	1.379 (5)	C8—C9	1.466 (7)
C1—S1	1.747 (3)	C8—C10	1.499 (6)
C2—C3	1.400 (7)	C8—H8	0.9800
C2—H2	0.9300	C9—H9A	0.9600
C3—C4	1.361 (8)	C9—H9B	0.9600
C3—H3	0.9300	C9—H9C	0.9600
C4—C5	1.361 (8)	C10—H10A	0.9600
C4—H4	0.9300	C10—H10B	0.9600
C5—C6	1.367 (6)	C10—H10C	0.9600
C5—H5	0.9300	N1—S1	1.637 (3)
C6—H6	0.9300	N1—H1N	0.81 (4)
C7—O3	1.202 (4)	O1—S1	1.420 (3)
C7—N1	1.378 (4)	O2—S1	1.435 (2)
C2—C1—C6	121.7 (3)	C9—C8—H8	107.5
C2—C1—S1	119.7 (3)	C10—C8—H8	107.5
C6—C1—S1	118.6 (3)	C7—C8—H8	107.5
C1—C2—C3	117.1 (4)	C8—C9—H9A	109.5
C1—C2—H2	121.4	C8—C9—H9B	109.5
C3—C2—H2	121.4	H9A—C9—H9B	109.5
C4—C3—C2	121.0 (4)	C8—C9—H9C	109.5
C4—C3—H3	119.5	H9A—C9—H9C	109.5
C2—C3—H3	119.5	H9B—C9—H9C	109.5
C5—C4—C3	120.8 (4)	C8—C10—H10A	109.5
C5—C4—H4	119.6	C8—C10—H10B	109.5
C3—C4—H4	119.6	H10A—C10—H10B	109.5
C4—C5—C6	119.7 (5)	C8—C10—H10C	109.5
C4—C5—H5	120.1	H10A—C10—H10C	109.5
C6—C5—H5	120.1	H10B—C10—H10C	109.5
C5—C6—C1	119.7 (4)	C7—N1—S1	125.3 (2)
C5—C6—H6	120.1	C7—N1—H1N	120 (3)
C1—C6—H6	120.1	S1—N1—H1N	114 (3)
O3—C7—N1	120.9 (3)	O1—S1—O2	118.90 (16)
O3—C7—C8	125.3 (3)	O1—S1—N1	110.43 (16)
N1—C7—C8	113.7 (3)	O2—S1—N1	103.49 (14)
C9—C8—C10	113.7 (5)	O1—S1—C1	108.82 (15)
C9—C8—C7	109.5 (4)	O2—S1—C1	108.49 (16)
C10—C8—C7	110.9 (4)	N1—S1—C1	105.91 (14)
C6—C1—C2—C3	0.2 (5)	O3—C7—N1—S1	−4.4 (5)
S1—C1—C2—C3	178.2 (3)	C8—C7—N1—S1	179.4 (3)
C1—C2—C3—C4	−0.8 (7)	C7—N1—S1—O1	−50.6 (3)
C2—C3—C4—C5	0.6 (8)	C7—N1—S1—O2	−178.9 (3)
C3—C4—C5—C6	0.2 (8)	C7—N1—S1—C1	67.1 (3)
C4—C5—C6—C1	−0.8 (7)	C2—C1—S1—O1	−179.6 (3)
C2—C1—C6—C5	0.6 (6)	C6—C1—S1—O1	−1.4 (3)
S1—C1—C6—C5	−177.5 (3)	C2—C1—S1—O2	−48.8 (3)
O3—C7—C8—C9	−88.9 (6)	C6—C1—S1—O2	129.3 (3)
N1—C7—C8—C9	87.0 (5)	C2—C1—S1—N1	61.7 (3)
O3—C7—C8—C10	37.3 (6)	C6—C1—S1—N1	−120.1 (3)
N1—C7—C8—C10	−146.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.81 (4)	2.12 (5)	2.898 (4)	160 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.81 (4)	2.12 (5)	2.898 (4)	160 (4)

Symmetry code: (i) .