o-Toluene-sulfonamide: a redetermination.

The structure of the title compound, C(7)H(9)NO(2)S, was previously determined from powder diffraction data [Tremayne, Seaton & Glidewell (2002). Acta Cryst. B58, 823-834]. It has now been refined to a significantly higher precision. The amino N-atom is bent with a C-C-S-N torsion angle of -65.8 (2)deg;. In the crystal, mol-ecules are packed into a three-dimensional framework/supramolecular structure through hydrogen bonds between the two H atoms of the sulfonamide group and sulfonyl O atoms of neighbouring mol-ecules.

Related literature

For our studies of the effect of substituents on the solid state structures of sulfonamides, see: Gowda et al. (2003 ▶, 2009 ▶); Gowda, Srilatha et al. (2007 ▶). For the parent benzene­sulfonamide, see: Gowda, Nayak et al. (2007 ▶). For other aryl sulfonamides, see: Gowda et al. (2003 ▶, 2009 ▶); Gowda, Srilatha et al. (2007 ▶); Jones & Weinkauf (1993 ▶); Kumar et al. (1992 ▶); O’Connor & Maslen (1965 ▶). For the powder structure of the title compound, see: Tremayne et al. (2002 ▶).

Experimental

Crystal data

C7H9NO2S

M = 171.21

Tetragonal,

a = 18.670 (3) Å

c = 9.057 (1) Å

V = 3157.0 (8) Å3

Z = 16

Cu Kα radiation

μ = 3.24 mm−1

T = 299 K

0.40 × 0.35 × 0.02 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.324, T max = 0.938

5320 measured reflections

1403 independent reflections

1290 reflections with I > 2σ(I)

R int = 0.059

3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.101

S = 1.07

1403 reflections

108 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.41 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/S1600536809033686/fl2262sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033686/fl2262Isup2.hkl

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

C7H9NO2S	Dx = 1.441 Mg m−3
Mr = 171.21	Cu Kα radiation, λ = 1.54180 Å
Tetragonal, I41/a	Cell parameters from 25 reflections
Hall symbol: -I 4ad	θ = 4.7–17.9°
a = 18.670 (3) Å	µ = 3.24 mm−1
c = 9.057 (1) Å	T = 299 K
V = 3157.0 (8) Å3	Prism, colourless
Z = 16	0.40 × 0.35 × 0.02 mm
F(000) = 1440

Enraf–Nonius CAD-4 diffractometer	1290 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
graphite	θmax = 66.8°, θmin = 4.7°
ω/2θ scans	h = −22→22
Absorption correction: ψ scan (North et al., 1968)	k = −22→22
Tmin = 0.324, Tmax = 0.938	l = −10→0
5320 measured reflections	3 standard reflections every 120 min
1403 independent reflections	intensity decay: 1.5%

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.101	w = 1/[σ2(Fo2) + (0.0529P)2 + 2.2812P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1403 reflections	Δρmax = 0.28 e Å−3
108 parameters	Δρmin = −0.41 e Å−3
2 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: 0.00227 (18)

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
S1	0.13337 (2)	0.12556 (2)	0.26312 (5)	0.0365 (2)
O1	0.20600 (8)	0.10124 (10)	0.24990 (15)	0.0543 (5)
O2	0.11947 (10)	0.20074 (8)	0.25836 (16)	0.0612 (5)
N1	0.09068 (10)	0.08933 (10)	0.13117 (18)	0.0454 (4)
H11	0.0510 (10)	0.1073 (12)	0.108 (3)	0.054*
H12	0.1053 (12)	0.0484 (10)	0.107 (3)	0.054*
C1	0.10065 (9)	0.09226 (9)	0.43325 (19)	0.0329 (4)
C2	0.03095 (11)	0.10630 (10)	0.4810 (2)	0.0395 (5)
C3	0.01179 (12)	0.07885 (12)	0.6185 (2)	0.0522 (5)
H3	−0.0341	0.0873	0.6542	0.063*
C4	0.05868 (14)	0.03960 (13)	0.7032 (2)	0.0575 (6)
H4	0.0441	0.0222	0.7946	0.069*
C5	0.12671 (13)	0.02595 (13)	0.6539 (2)	0.0545 (6)
H5	0.1583	−0.0007	0.7113	0.065*
C6	0.14805 (11)	0.05211 (11)	0.5179 (2)	0.0430 (5)
H6	0.1940	0.0429	0.4832	0.052*
C7	−0.02347 (13)	0.14733 (13)	0.3939 (3)	0.0609 (6)
H7A	−0.0344	0.1218	0.3047	0.073*
H7B	−0.0046	0.1937	0.3695	0.073*
H7C	−0.0663	0.1529	0.4515	0.073*

	U11	U22	U33	U12	U13	U23
S1	0.0422 (3)	0.0384 (3)	0.0289 (3)	−0.00894 (17)	−0.00042 (16)	0.00272 (16)
O1	0.0375 (8)	0.0865 (12)	0.0388 (8)	−0.0106 (7)	0.0015 (6)	0.0054 (7)
O2	0.1032 (14)	0.0364 (8)	0.0441 (9)	−0.0154 (8)	0.0039 (8)	0.0066 (6)
N1	0.0483 (10)	0.0500 (10)	0.0378 (9)	0.0088 (8)	−0.0116 (7)	−0.0078 (7)
C1	0.0401 (10)	0.0305 (8)	0.0281 (8)	−0.0057 (7)	−0.0005 (7)	−0.0006 (7)
C2	0.0427 (11)	0.0357 (10)	0.0401 (10)	−0.0035 (8)	0.0019 (8)	−0.0061 (7)
C3	0.0541 (13)	0.0591 (13)	0.0435 (11)	−0.0101 (10)	0.0151 (9)	−0.0081 (9)
C4	0.0769 (16)	0.0612 (14)	0.0345 (10)	−0.0178 (12)	0.0063 (10)	0.0060 (10)
C5	0.0673 (15)	0.0549 (13)	0.0413 (12)	−0.0066 (10)	−0.0086 (10)	0.0160 (9)
C6	0.0445 (11)	0.0439 (11)	0.0405 (10)	−0.0014 (8)	−0.0025 (8)	0.0056 (8)
C7	0.0474 (12)	0.0632 (14)	0.0721 (16)	0.0123 (11)	0.0017 (11)	0.0027 (12)

S1—O2	1.4281 (16)	C3—C4	1.375 (4)
S1—O1	1.4349 (16)	C3—H3	0.9300
S1—N1	1.5877 (17)	C4—C5	1.370 (3)
S1—C1	1.7703 (17)	C4—H4	0.9300
N1—H11	0.839 (16)	C5—C6	1.384 (3)
N1—H12	0.841 (16)	C5—H5	0.9300
C1—C6	1.390 (3)	C6—H6	0.9300
C1—C2	1.396 (3)	C7—H7A	0.9600
C2—C3	1.394 (3)	C7—H7B	0.9600
C2—C7	1.497 (3)	C7—H7C	0.9600
O2—S1—O1	118.70 (11)	C2—C3—H3	119.0
O2—S1—N1	107.74 (10)	C5—C4—C3	120.5 (2)
O1—S1—N1	106.07 (9)	C5—C4—H4	119.8
O2—S1—C1	107.98 (9)	C3—C4—H4	119.8
O1—S1—C1	106.72 (8)	C4—C5—C6	119.4 (2)
N1—S1—C1	109.41 (9)	C4—C5—H5	120.3
S1—N1—H11	117.3 (17)	C6—C5—H5	120.3
S1—N1—H12	114.9 (17)	C5—C6—C1	119.9 (2)
H11—N1—H12	126 (2)	C5—C6—H6	120.1
C6—C1—C2	121.59 (17)	C1—C6—H6	120.1
C6—C1—S1	116.72 (15)	C2—C7—H7A	109.5
C2—C1—S1	121.69 (14)	C2—C7—H7B	109.5
C3—C2—C1	116.55 (19)	H7A—C7—H7B	109.5
C3—C2—C7	119.0 (2)	C2—C7—H7C	109.5
C1—C2—C7	124.44 (19)	H7A—C7—H7C	109.5
C4—C3—C2	122.1 (2)	H7B—C7—H7C	109.5
C4—C3—H3	119.0
O2—S1—C1—C6	−128.04 (16)	S1—C1—C2—C7	2.5 (3)
O1—S1—C1—C6	0.61 (17)	C1—C2—C3—C4	−0.3 (3)
N1—S1—C1—C6	114.96 (15)	C7—C2—C3—C4	178.8 (2)
O2—S1—C1—C2	51.23 (17)	C2—C3—C4—C5	−0.2 (3)
O1—S1—C1—C2	179.89 (15)	C3—C4—C5—C6	0.1 (4)
N1—S1—C1—C2	−65.77 (17)	C4—C5—C6—C1	0.4 (3)
C6—C1—C2—C3	0.9 (3)	C2—C1—C6—C5	−0.9 (3)
S1—C1—C2—C3	−178.38 (14)	S1—C1—C6—C5	178.33 (17)
C6—C1—C2—C7	−178.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O2i	0.84 (2)	2.19 (2)	3.003 (2)	162 (2)
N1—H12···O1ii	0.84 (2)	2.14 (2)	2.964 (2)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O2i	0.839 (16)	2.193 (18)	3.003 (2)	162 (2)
N1—H12⋯O1ii	0.841 (16)	2.138 (17)	2.964 (2)	167 (2)

Symmetry codes: (i) ; (ii) .