2-Chloro-N-[(2-methyl-phen-yl)sulfon-yl]acetamide.

In the title compound, C(9)H(10)ClNO(3)S, the amide H atom is syn with respect to the ortho-methyl group in the benzene ring and the C-S-N-C torsion angle is -66.9 (2)°. An intra-molecular N-H⋯Cl hydrogen bond occurs. 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 hydrogen-bonding preferences of sulfonamides, see; Adsmond & Grant (2001 ▶). For the effect of substituents on the crystal structures of sulfono­amides, see: Gowda et al. (2008 ▶, 2010 ▶)

Experimental

Crystal data

C9H10ClNO3S

M = 247.69

Triclinic,

a = 7.4439 (8) Å

b = 7.5195 (8) Å

c = 10.519 (1) Å

α = 93.64 (1)°

β = 109.72 (1)°

γ = 102.52 (1)°

V = 535.07 (10) Å3

Z = 2

Cu Kα radiation

μ = 4.90 mm−1

T = 299 K

0.50 × 0.40 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.193, T max = 0.473

3727 measured reflections

1891 independent reflections

1771 reflections with I > 2σ(I)

R int = 0.051

3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.137

S = 1.08

1891 reflections

141 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.57 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/S1600536811003655/ds2090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003655/ds2090Isup2.hkl

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

C9H10ClNO3S	Z = 2
Mr = 247.69	F(000) = 256
Triclinic, P1	Dx = 1.537 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 7.4439 (8) Å	Cell parameters from 25 reflections
b = 7.5195 (8) Å	θ = 7.0–23.1°
c = 10.519 (1) Å	µ = 4.90 mm−1
α = 93.64 (1)°	T = 299 K
β = 109.72 (1)°	Prism, colourless
γ = 102.52 (1)°	0.50 × 0.40 × 0.18 mm
V = 535.07 (10) Å3

Enraf–Nonius CAD-4 diffractometer	1771 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
graphite	θmax = 66.9°, θmin = 4.5°
ω/2θ scans	h = −8→8
Absorption correction: ψ scan (North et al., 1968)	k = −8→8
Tmin = 0.193, Tmax = 0.473	l = −12→12
3727 measured reflections	3 standard reflections every 120 min
1891 independent reflections	intensity decay: 0.5%

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0853P)2 + 0.2427P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
1891 reflections	Δρmax = 0.52 e Å−3
141 parameters	Δρmin = −0.57 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: 0.028 (3)

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	0.4813 (4)	0.6426 (3)	0.3198 (2)	0.0356 (6)
C2	0.6844 (5)	0.7012 (3)	0.3580 (3)	0.0465 (7)
C3	0.7891 (6)	0.7927 (4)	0.4905 (3)	0.0674 (10)
H3	0.9259	0.8321	0.5206	0.081*
C4	0.6944 (8)	0.8259 (5)	0.5778 (3)	0.0764 (13)
H4	0.7682	0.8892	0.6653	0.092*
C5	0.4938 (8)	0.7680 (5)	0.5388 (3)	0.0754 (12)
H5	0.4320	0.7916	0.5992	0.090*
C6	0.3832 (6)	0.6737 (4)	0.4081 (3)	0.0531 (8)
H6	0.2468	0.6321	0.3800	0.064*
C7	0.2227 (4)	0.8123 (3)	0.0563 (2)	0.0336 (5)
C8	0.1973 (4)	0.9327 (3)	−0.0539 (3)	0.0397 (6)
H8A	0.2593	1.0596	−0.0110	0.048*
H8B	0.0574	0.9224	−0.0984	0.048*
C9	0.7974 (5)	0.6716 (5)	0.2685 (4)	0.0622 (8)
H9A	0.7241	0.6847	0.1766	0.075*
H9B	0.8181	0.5500	0.2704	0.075*
H9C	0.9226	0.7610	0.3010	0.075*
N1	0.3146 (3)	0.6745 (3)	0.05184 (19)	0.0327 (5)
H1N	0.366 (4)	0.660 (4)	−0.001 (3)	0.039*
O1	0.4251 (3)	0.3986 (2)	0.11017 (18)	0.0450 (5)
O2	0.1386 (3)	0.4445 (3)	0.1603 (2)	0.0516 (5)
O3	0.1615 (3)	0.8425 (3)	0.14615 (19)	0.0504 (5)
Cl1	0.29367 (12)	0.88507 (9)	−0.18091 (7)	0.0525 (3)
S1	0.32891 (8)	0.51904 (7)	0.15752 (5)	0.0320 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0487 (16)	0.0278 (10)	0.0267 (11)	0.0120 (10)	0.0075 (10)	0.0051 (8)
C2	0.0512 (18)	0.0318 (12)	0.0458 (14)	0.0066 (11)	0.0055 (12)	0.0113 (10)
C3	0.076 (3)	0.0459 (16)	0.0511 (18)	0.0051 (15)	−0.0078 (16)	0.0068 (13)
C4	0.112 (4)	0.0511 (18)	0.0400 (17)	0.017 (2)	−0.0020 (19)	−0.0004 (13)
C5	0.137 (4)	0.070 (2)	0.0381 (16)	0.051 (2)	0.039 (2)	0.0132 (14)
C6	0.076 (2)	0.0538 (16)	0.0392 (14)	0.0305 (15)	0.0231 (14)	0.0143 (11)
C7	0.0357 (13)	0.0325 (11)	0.0310 (11)	0.0118 (9)	0.0084 (9)	0.0030 (8)
C8	0.0451 (16)	0.0363 (12)	0.0417 (13)	0.0181 (11)	0.0150 (11)	0.0101 (10)
C9	0.0466 (19)	0.0606 (18)	0.076 (2)	0.0087 (14)	0.0209 (15)	0.0130 (15)
N1	0.0407 (12)	0.0335 (10)	0.0287 (9)	0.0161 (8)	0.0141 (8)	0.0063 (8)
O1	0.0661 (14)	0.0323 (9)	0.0412 (9)	0.0231 (9)	0.0185 (9)	0.0057 (7)
O2	0.0432 (12)	0.0498 (11)	0.0537 (11)	−0.0001 (9)	0.0134 (9)	0.0151 (8)
O3	0.0648 (14)	0.0597 (12)	0.0438 (10)	0.0355 (10)	0.0277 (10)	0.0130 (8)
Cl1	0.0744 (6)	0.0547 (5)	0.0462 (4)	0.0325 (4)	0.0314 (4)	0.0216 (3)
S1	0.0384 (4)	0.0259 (4)	0.0298 (4)	0.0087 (3)	0.0093 (3)	0.0049 (2)

C1—C2	1.386 (4)	C7—N1	1.367 (3)
C1—C6	1.398 (4)	C7—C8	1.502 (3)
C1—S1	1.760 (2)	C8—Cl1	1.768 (3)
C2—C3	1.392 (4)	C8—H8A	0.9700
C2—C9	1.494 (5)	C8—H8B	0.9700
C3—C4	1.374 (7)	C9—H9A	0.9600
C3—H3	0.9300	C9—H9B	0.9600
C4—C5	1.367 (6)	C9—H9C	0.9600
C4—H4	0.9300	N1—S1	1.6590 (19)
C5—C6	1.389 (5)	N1—H1N	0.79 (2)
C5—H5	0.9300	O1—S1	1.4303 (18)
C6—H6	0.9300	O2—S1	1.417 (2)
C7—O3	1.208 (3)
C2—C1—C6	122.5 (2)	C7—C8—Cl1	116.35 (17)
C2—C1—S1	122.3 (2)	C7—C8—H8A	108.2
C6—C1—S1	115.3 (2)	Cl1—C8—H8A	108.2
C1—C2—C3	116.8 (3)	C7—C8—H8B	108.2
C1—C2—C9	124.9 (2)	Cl1—C8—H8B	108.2
C3—C2—C9	118.3 (3)	H8A—C8—H8B	107.4
C4—C3—C2	121.3 (4)	C2—C9—H9A	109.5
C4—C3—H3	119.4	C2—C9—H9B	109.5
C2—C3—H3	119.4	H9A—C9—H9B	109.5
C5—C4—C3	121.4 (3)	C2—C9—H9C	109.5
C5—C4—H4	119.3	H9A—C9—H9C	109.5
C3—C4—H4	119.3	H9B—C9—H9C	109.5
C4—C5—C6	119.4 (3)	C7—N1—S1	123.27 (17)
C4—C5—H5	120.3	C7—N1—H1N	124 (2)
C6—C5—H5	120.3	S1—N1—H1N	113 (2)
C5—C6—C1	118.7 (4)	O2—S1—O1	118.71 (12)
C5—C6—H6	120.7	O2—S1—N1	108.92 (11)
C1—C6—H6	120.7	O1—S1—N1	103.64 (10)
O3—C7—N1	122.6 (2)	O2—S1—C1	108.50 (12)
O3—C7—C8	118.3 (2)	O1—S1—C1	110.83 (12)
N1—C7—C8	119.1 (2)	N1—S1—C1	105.34 (10)
C6—C1—C2—C3	0.5 (4)	N1—C7—C8—Cl1	−0.7 (3)
S1—C1—C2—C3	−178.1 (2)	O3—C7—N1—S1	7.4 (4)
C6—C1—C2—C9	179.8 (3)	C8—C7—N1—S1	−172.97 (18)
S1—C1—C2—C9	1.2 (4)	C7—N1—S1—O2	49.3 (2)
C1—C2—C3—C4	−1.2 (4)	C7—N1—S1—O1	176.60 (19)
C9—C2—C3—C4	179.4 (3)	C7—N1—S1—C1	−66.9 (2)
C2—C3—C4—C5	1.0 (5)	C2—C1—S1—O2	167.1 (2)
C3—C4—C5—C6	0.0 (5)	C6—C1—S1—O2	−11.5 (2)
C4—C5—C6—C1	−0.7 (5)	C2—C1—S1—O1	35.1 (2)
C2—C1—C6—C5	0.4 (4)	C6—C1—S1—O1	−143.56 (19)
S1—C1—C6—C5	179.1 (2)	C2—C1—S1—N1	−76.3 (2)
O3—C7—C8—Cl1	178.8 (2)	C6—C1—S1—N1	105.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.79 (2)	2.32 (2)	3.087 (3)	166 (3)
N1—H1N···Cl1	0.79 (2)	2.62 (3)	2.978 (2)	110 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.79 (2)	2.32 (2)	3.087 (3)	166 (3)
N1—H1N⋯Cl1	0.79 (2)	2.62 (3)	2.978 (2)	110 (2)

Symmetry code: (i) .