2-Amino-4-methyl­benzene­sulfonamide

Qian, S.-S.; Hu, H.; Cui, H.-Y.

doi:10.1107/S1600536809037271

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2513

doi:10.1107/S1600536809037271

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2-Amino-4-methylbenzenesulfonamide

Shao-Song Qian,^a ^* Hao Hu ^a and Hong-You Cui ^b

^aSchool of Life, ShanDong University of Technology, ZiBo 255049, People's Republic of China, and ^bSchool of Chemical Engineering, ShanDong University of Technology, ZiBo 255049, People's Republic of China
^*Correspondence e-mail: njuqss@yahoo.com.cn

(Received 5 September 2009; accepted 15 September 2009; online 26 September 2009)

In the crystal of the title compound, C₇H₁₀N₂O₂S, the molecules are linked by two strong N—H⋯O hydrogen bonds. The molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond. The C/S/N plane makes a dihedral angle of 69.7 (2)° with the aromatic ring plane.

Related literature

For the anticonvulsant activity of the title compound and its derivatives, see: Monzani et al. (1985 ); Tait et al. (1993 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₇H₁₀N₂O₂S
M_r = 186.23
Monoclinic, P 2₁ /c
a = 9.873 (5) Å
b = 9.151 (4) Å
c = 10.408 (5) Å
β = 114.689 (6)°
V = 854.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 273 K
0.16 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.948, T_max = 0.967
4115 measured reflections
1449 independent reflections
1338 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.132
S = 1.10
1449 reflections
110 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2ⁱ	0.86	2.15	3.003 (4)	174
N2—H2A⋯O1ⁱⁱ	0.86	2.27	2.975 (4)	139
N1—H1B⋯O2	0.86	2.60	3.080 (5)	117
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037271/bx2239sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037271/bx2239Isup2.hkl

checkCIF report

Comment top

The title compound (I), Figure1, was prepared and tested for anticonvulsant activity in mice, (Monzani, et al.,1985). In addition, its derivatives was studied using indomethacin as a reference drug (Tait, et al.,1993). We report here its crystal and molecular structure. The molecules are linked by two strong N—H···O generating a graph-set motif R⁴₄(16) ring (Bernstein, et al., 1995) and is stabilized by one N—H···O intramolecular hydrogen bonds (Table1, Figure 2). The C2/S1/N2 plane makes a dihedral angle of 69.7 (2)° with the aromatic ring plane.

Related literature top

For the anticonvulsant activity of the title compound andits derivatives, see: Monzani et al. (1985); Tait et al. (1993). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized according to method described by Monzani, et al.,1985.The single crystals suitable for X-ray diffraction were obtained by spontaneous evaporation of the solvent.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level.
	Fig. 2. A portion of the packing diagram for (I) showing graph-set motif R⁴₄(16) ring. For the sake clarity the atoms not involved in the motif shown have been omitted Symmetry codes: (i) x, -y+1/2, z+1/2; (ii)-x,y+1/2,-z+3/2.

2-Amino-4-methylbenzenesulfonamide top

Crystal data top

C₇H₁₀N₂O₂S	F(000) = 392
M_r = 186.23	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3354 reflections
a = 9.873 (5) Å	θ = 2.2–28.2°
b = 9.151 (4) Å	µ = 0.34 mm⁻¹
c = 10.408 (5) Å	T = 273 K
β = 114.689 (6)°	Block, colorless
V = 854.4 (7) Å³	0.16 × 0.13 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1449 independent reflections
Radiation source: fine-focus sealed tube	1338 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 25.1°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.948, T_max = 0.967	k = −10→10
4115 measured reflections	l = −12→9

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0721P)² + 0.701P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
1449 reflections	Δρ_max = 0.56 e Å⁻³
110 parameters	Δρ_min = −0.41 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: 0.047 (9)

Crystal data top

C₇H₁₀N₂O₂S	V = 854.4 (7) Å³
M_r = 186.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.873 (5) Å	µ = 0.34 mm⁻¹
b = 9.151 (4) Å	T = 273 K
c = 10.408 (5) Å	0.16 × 0.13 × 0.10 mm
β = 114.689 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1449 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1338 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.967	R_int = 0.017
4115 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.10	Δρ_max = 0.56 e Å⁻³
1449 reflections	Δρ_min = −0.41 e Å⁻³
110 parameters

Special details top

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
S1	0.13944 (9)	0.19821 (9)	0.76214 (8)	0.0361 (4)
O1	0.1511 (3)	0.0560 (3)	0.8246 (3)	0.0533 (8)
O2	0.0800 (3)	0.2040 (4)	0.6109 (3)	0.0603 (9)
N1	0.2315 (4)	0.5060 (4)	0.6773 (4)	0.0604 (10)
H1A	0.2566	0.5867	0.6510	0.073*
H1B	0.1391	0.4815	0.6450	0.073*
N2	0.0260 (3)	0.2896 (3)	0.8048 (3)	0.0412 (7)
H2A	−0.0514	0.3293	0.7402	0.049*
H2B	0.0426	0.2990	0.8924	0.049*
C1	0.3488 (4)	0.4078 (4)	0.7793 (3)	0.0357 (7)
C2	0.3186 (3)	0.2754 (4)	0.8318 (3)	0.0342 (7)
C3	0.4324 (4)	0.1967 (4)	0.9361 (4)	0.0396 (8)
H3	0.4098	0.1121	0.9727	0.048*
C4	0.5787 (4)	0.2433 (4)	0.9859 (4)	0.0443 (9)
H4	0.6543	0.1920	1.0571	0.053*
C5	0.6107 (3)	0.3669 (4)	0.9282 (4)	0.0417 (8)
C6	0.4979 (4)	0.4501 (4)	0.8300 (4)	0.0406 (8)
H6	0.5221	0.5362	0.7969	0.049*
C7	0.7610 (3)	0.4151 (5)	0.9737 (4)	0.0497 (9)
H7A	0.7795	0.4947	1.0389	0.074*
H7B	0.7771	0.4471	0.8933	0.074*
H7C	0.8276	0.3360	1.0193	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0355 (6)	0.0364 (6)	0.0356 (6)	−0.0058 (3)	0.0140 (4)	−0.0071 (3)
O1	0.0470 (15)	0.0348 (14)	0.0722 (18)	−0.0059 (11)	0.0191 (13)	−0.0030 (12)
O2	0.0540 (16)	0.086 (2)	0.0376 (14)	−0.0211 (14)	0.0163 (12)	−0.0185 (13)
N1	0.056 (2)	0.063 (2)	0.062 (2)	0.0026 (16)	0.0245 (17)	0.0197 (17)
N2	0.0373 (16)	0.0455 (17)	0.0419 (15)	0.0014 (12)	0.0174 (13)	0.0004 (12)
C1	0.0368 (16)	0.0390 (17)	0.0348 (15)	0.0007 (13)	0.0184 (13)	−0.0019 (13)
C2	0.0329 (16)	0.0357 (16)	0.0352 (16)	−0.0012 (12)	0.0155 (13)	−0.0053 (12)
C3	0.0414 (18)	0.0327 (17)	0.0435 (18)	0.0024 (13)	0.0165 (15)	0.0001 (13)
C4	0.0360 (18)	0.0431 (19)	0.0474 (19)	0.0067 (14)	0.0109 (15)	−0.0027 (16)
C5	0.0313 (17)	0.047 (2)	0.0467 (18)	−0.0029 (14)	0.0165 (14)	−0.0113 (15)
C6	0.0395 (17)	0.0420 (18)	0.0443 (18)	−0.0051 (14)	0.0213 (15)	−0.0005 (15)
C7	0.0246 (16)	0.058 (2)	0.062 (2)	−0.0056 (15)	0.0139 (16)	−0.0010 (18)

Geometric parameters (Å, º) top

S1—O2	1.433 (3)	C2—C3	1.393 (5)
S1—O1	1.438 (3)	C3—C4	1.383 (5)
S1—N2	1.602 (3)	C3—H3	0.9300
S1—C2	1.756 (3)	C4—C5	1.378 (6)
N1—C1	1.500 (5)	C4—H4	0.9300
N1—H1A	0.8600	C5—C6	1.383 (5)
N1—H1B	0.8600	C5—C7	1.426 (4)
N2—H2A	0.8600	C6—H6	0.9300
N2—H2B	0.8600	C7—H7A	0.9600
C1—C6	1.395 (5)	C7—H7B	0.9600
C1—C2	1.412 (5)	C7—H7C	0.9600

O2—S1—O1	116.68 (18)	C4—C3—C2	120.6 (3)
O2—S1—N2	105.80 (18)	C4—C3—H3	119.7
O1—S1—N2	106.29 (16)	C2—C3—H3	119.7
O2—S1—C2	108.58 (16)	C5—C4—C3	118.9 (3)
O1—S1—C2	107.49 (16)	C5—C4—H4	120.5
N2—S1—C2	112.08 (16)	C3—C4—H4	120.5
C1—N1—H1A	120.0	C4—C5—C6	120.9 (3)
C1—N1—H1B	120.0	C4—C5—C7	120.3 (3)
H1A—N1—H1B	120.0	C6—C5—C7	118.7 (4)
S1—N2—H2A	120.0	C5—C6—C1	121.5 (3)
S1—N2—H2B	120.0	C5—C6—H6	119.2
H2A—N2—H2B	120.0	C1—C6—H6	119.2
C6—C1—C2	116.9 (3)	C5—C7—H7A	109.5
C6—C1—N1	118.9 (3)	C5—C7—H7B	109.5
C2—C1—N1	124.3 (3)	H7A—C7—H7B	109.5
C3—C2—C1	120.9 (3)	C5—C7—H7C	109.5
C3—C2—S1	117.4 (3)	H7A—C7—H7C	109.5
C1—C2—S1	121.6 (3)	H7B—C7—H7C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2ⁱ	0.86	2.15	3.003 (4)	174
N2—H2A···O1ⁱⁱ	0.86	2.27	2.975 (4)	139
N1—H1B···O2	0.86	2.60	3.080 (5)	117

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₇H₁₀N₂O₂S
M_r	186.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	9.873 (5), 9.151 (4), 10.408 (5)
β (°)	114.689 (6)
V (Å³)	854.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.16 × 0.13 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.948, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	4115, 1449, 1338
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.132, 1.10
No. of reflections	1449
No. of parameters	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.41

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2ⁱ	0.86	2.15	3.003 (4)	173.5
N2—H2A···O1ⁱⁱ	0.86	2.27	2.975 (4)	138.6
N1—H1B···O2	0.86	2.60	3.080 (5)	116.7

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x, y+1/2, −z+3/2.

Acknowledgements

This project was sponsored by the ShanDong Province Science & Technology Innovation Foundation.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Monzani, A., Gamberini, G., Braghiroli, D., Di Bella, M., Raffa, L. & Sandrini, M. (1985). Arch. Pharm. 318, 299–304. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tait, A., Parenti, C., Zanoli, P., Veneri, C., Truzzi, C., Brandoli, C., Baraldi, M. & Di Bella, M. (1993). Farmaco, 48, 1463–1473. CAS PubMed Web of Science Google Scholar