5-Amino-2-methyl­benzene­sulfonamide

Ma, X.-J.; Fang, Z.; Ren, L.-L.; Wei, P.

doi:10.1107/S1600536809026142

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1815

doi:10.1107/S1600536809026142

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5-Amino-2-methylbenzenesulfonamide

Xiang-Jun Ma,^a Zheng Fang,^b ^* Li-Li Ren ^b and Ping Wei ^a

^aSchool of Biotechnology and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^bSchool of Pharmaceutical Sciences, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: fzcpu@163.com

(Received 26 June 2009; accepted 5 July 2009; online 11 July 2009)

In the crystal structure of the title compound, C₇H₁₀N₂O₂S, a benzoic acid derivative, intermolecular N—H⋯O interactions link the molecules into a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₇H₁₀N₂O₂S
M_r = 186.23
Orthorhombic, I b a 2
a = 10.679 (2) Å
b = 22.431 (5) Å
c = 7.1980 (14) Å
V = 1724.2 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 294 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.906, T_max = 0.967
1587 measured reflections
1432 independent reflections
1369 reflections with I > 2σ(I)
R_int = 0.044
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.120
S = 1.00
1432 reflections
111 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.35 e Å⁻³
Absolute structure: Flack (1983 ), 576 Friedel pairs
Flack parameter: 0.04 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O2ⁱ	0.86	2.27	2.996 (4)	142
N1—H1C⋯O1ⁱⁱ	0.86	2.16	3.001 (4)	164
N2—H2C⋯O1ⁱⁱⁱ	0.86	2.60	3.278 (4)	137
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x, y, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026142/hk2722sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026142/hk2722Isup2.hkl

checkCIF report

Comment top

Some derivatives of benzoic acid are important chemical materials. We report herein the crystal structure of the title compound.

In the molecule of the title compound, (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C2-C7) is, of course, planar. Atoms S, O1, N2 and C1 are 0.013 (3), -0.102 (3), -0.027 (3) and -0.032 (3) Å away from the plane of ring A, respectively.

In the crystal structure, intermolecular N-H···O interactions (Table 1) link the molecules into a three-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, ammonium hydroxide (25 ml) was added to N-acetylamino-2-toluenesulfonyl chloride (10.7 g). The mixture was cooled down, and sulfuric acid solution (10 ml, 20%) was slowly added. The mixture was kept at 273–278 K for 5 min. The corresponding sulfonamide was collected, washed with ice water and dried to give a crystalline crude colorless solid (yield; 67%). Then, hydrochloric acid (15 ml, 18%) was added to N-acetyltoluenesulfonamide (5.6 g) and the mixture was refluxed for 20 min. The resulting solution was diluted with an equal volume of water and sodium carbonate until pH = 8. After cooling, the precipitate was collected and washed with ice water (yield; 3.9 g). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

5-Amino-2-methylbenzenesulfonamide top

Crystal data top

C₇H₁₀N₂O₂S	F(000) = 784
M_r = 186.23	D_x = 1.435 Mg m⁻³
Orthorhombic, Iba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2c	Cell parameters from 25 reflections
a = 10.679 (2) Å	θ = 10–14°
b = 22.431 (5) Å	µ = 0.34 mm⁻¹
c = 7.1980 (14) Å	T = 294 K
V = 1724.2 (6) Å³	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1369 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 25.3°, θ_min = 1.8°
ω/2θ scans	h = −12→0
Absorption correction: ψ scan (North et al., 1968)	k = −26→8
T_min = 0.906, T_max = 0.967	l = −8→8
1587 measured reflections	3 standard reflections every 120 min
1432 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.1P)² + 0.35P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.120	(Δ/σ)_max < 0.001
S = 1.00	Δρ_max = 0.29 e Å⁻³
1432 reflections	Δρ_min = −0.35 e Å⁻³
111 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.019 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 576 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.04 (14)

Crystal data top

C₇H₁₀N₂O₂S	V = 1724.2 (6) Å³
M_r = 186.23	Z = 8
Orthorhombic, Iba2	Mo Kα radiation
a = 10.679 (2) Å	µ = 0.34 mm⁻¹
b = 22.431 (5) Å	T = 294 K
c = 7.1980 (14) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1369 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.044
T_min = 0.906, T_max = 0.967	3 standard reflections every 120 min
1587 measured reflections	intensity decay: 1%
1432 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.120	Δρ_max = 0.29 e Å⁻³
S = 1.00	Δρ_min = −0.35 e Å⁻³
1432 reflections	Absolute structure: Flack (1983), 576 Friedel pairs
111 parameters	Absolute structure parameter: 0.04 (14)
1 restraint

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
S	0.16988 (6)	0.09021 (3)	0.64671 (14)	0.0332 (3)
O1	0.06327 (19)	0.12096 (9)	0.5690 (4)	0.0469 (6)
N1	0.1216 (3)	0.05631 (12)	0.8282 (5)	0.0495 (8)
H1B	0.1362	0.0189	0.8419	0.059*
H1C	0.0810	0.0755	0.9123	0.059*
C1	0.4280 (3)	0.06855 (16)	0.8644 (6)	0.0527 (9)
H1D	0.5127	0.0686	0.9089	0.079*
H1E	0.4210	0.0420	0.7604	0.079*
H1F	0.3730	0.0555	0.9618	0.079*
O2	0.2333 (2)	0.04672 (10)	0.5348 (4)	0.0511 (7)
N2	0.3024 (3)	0.30886 (10)	0.6676 (5)	0.0489 (8)
H2B	0.2329	0.3169	0.6125	0.059*
H2C	0.3532	0.3372	0.6962	0.059*
C2	0.3922 (2)	0.13040 (13)	0.8053 (4)	0.0316 (6)
C3	0.2794 (2)	0.14549 (11)	0.7132 (4)	0.0272 (6)
C4	0.2507 (2)	0.20373 (11)	0.6649 (5)	0.0287 (6)
H4A	0.1767	0.2118	0.6017	0.034*
C5	0.3323 (3)	0.25064 (13)	0.7103 (5)	0.0318 (7)
C6	0.4439 (3)	0.23609 (14)	0.8042 (5)	0.0357 (7)
H6A	0.4997	0.2662	0.8367	0.043*
C7	0.4711 (3)	0.17810 (14)	0.8483 (4)	0.0363 (7)
H7A	0.5458	0.1701	0.9098	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0294 (4)	0.0314 (4)	0.0390 (5)	−0.0021 (2)	−0.0014 (3)	−0.0050 (3)
O1	0.0350 (11)	0.0441 (12)	0.0615 (15)	−0.0049 (10)	−0.0151 (11)	0.0014 (11)
N1	0.0459 (16)	0.0367 (14)	0.066 (2)	0.0010 (12)	0.0155 (16)	0.0131 (13)
C1	0.0487 (19)	0.0423 (17)	0.067 (2)	0.0114 (15)	−0.016 (2)	0.0051 (18)
O2	0.0447 (14)	0.0482 (13)	0.0603 (17)	−0.0016 (10)	0.0036 (12)	−0.0242 (12)
N2	0.0561 (15)	0.0312 (12)	0.059 (2)	−0.0070 (11)	−0.0146 (18)	0.0069 (14)
C2	0.0283 (14)	0.0348 (15)	0.0317 (15)	0.0046 (11)	0.0002 (12)	−0.0003 (11)
C3	0.0236 (12)	0.0307 (13)	0.0273 (13)	0.0010 (10)	0.0024 (11)	−0.0021 (11)
C4	0.0249 (12)	0.0330 (13)	0.0281 (15)	−0.0009 (10)	−0.0035 (12)	0.0019 (11)
C5	0.0374 (14)	0.0322 (14)	0.0258 (14)	0.0000 (10)	0.0029 (12)	0.0010 (11)
C6	0.0309 (13)	0.0422 (16)	0.0339 (15)	−0.0101 (12)	−0.0014 (13)	−0.0054 (13)
C7	0.0248 (14)	0.0503 (17)	0.0338 (16)	0.0022 (11)	−0.0052 (12)	−0.0034 (11)

Geometric parameters (Å, º) top

S—O2	1.435 (2)	N2—H2B	0.8600
S—O1	1.444 (2)	N2—H2C	0.8600
S—N1	1.597 (3)	C2—C7	1.397 (4)
S—C3	1.770 (3)	C2—C3	1.416 (4)
N1—H1B	0.8600	C3—C4	1.386 (4)
N1—H1C	0.8600	C4—C5	1.405 (4)
C1—C2	1.501 (4)	C4—H4A	0.9300
C1—H1D	0.9600	C5—C6	1.408 (4)
C1—H1E	0.9600	C6—C7	1.370 (5)
C1—H1F	0.9600	C6—H6A	0.9300
N2—C5	1.379 (4)	C7—H7A	0.9300

O2—S—O1	118.64 (18)	C7—C2—C3	115.7 (3)
O2—S—N1	106.75 (16)	C7—C2—C1	119.5 (3)
O1—S—N1	106.85 (15)	C3—C2—C1	124.8 (3)
O2—S—C3	108.43 (14)	C4—C3—C2	122.1 (2)
O1—S—C3	106.92 (12)	C4—C3—S	116.5 (2)
N1—S—C3	108.98 (17)	C2—C3—S	121.4 (2)
S—N1—H1B	120.0	C3—C4—C5	120.7 (3)
S—N1—H1C	120.0	C3—C4—H4A	119.7
H1B—N1—H1C	120.0	C5—C4—H4A	119.7
C2—C1—H1D	109.5	N2—C5—C4	120.9 (3)
C2—C1—H1E	109.5	N2—C5—C6	121.5 (3)
H1D—C1—H1E	109.5	C4—C5—C6	117.6 (3)
C2—C1—H1F	109.5	C7—C6—C5	120.7 (3)
H1D—C1—H1F	109.5	C7—C6—H6A	119.7
H1E—C1—H1F	109.5	C5—C6—H6A	119.7
C5—N2—H2B	120.0	C6—C7—C2	123.3 (3)
C5—N2—H2C	120.0	C6—C7—H7A	118.4
H2B—N2—H2C	120.0	C2—C7—H7A	118.4

C7—C2—C3—C4	1.5 (5)	C2—C3—C4—C5	−1.6 (5)
C1—C2—C3—C4	178.9 (3)	S—C3—C4—C5	−179.5 (2)
C7—C2—C3—S	179.3 (2)	C3—C4—C5—N2	−177.9 (3)
C1—C2—C3—S	−3.3 (5)	C3—C4—C5—C6	0.7 (5)
O2—S—C3—C4	123.0 (3)	N2—C5—C6—C7	178.9 (3)
O1—S—C3—C4	−6.0 (3)	C4—C5—C6—C7	0.3 (5)
N1—S—C3—C4	−121.1 (3)	C5—C6—C7—C2	−0.3 (5)
O2—S—C3—C2	−54.9 (3)	C3—C2—C7—C6	−0.6 (5)
O1—S—C3—C2	176.1 (3)	C1—C2—C7—C6	−178.1 (3)
N1—S—C3—C2	61.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2ⁱ	0.86	2.27	2.996 (4)	142
N1—H1C···O1ⁱⁱ	0.86	2.16	3.001 (4)	164
N2—H2C···O1ⁱⁱⁱ	0.86	2.60	3.278 (4)	137

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

Experimental details

Crystal data
Chemical formula	C₇H₁₀N₂O₂S
M_r	186.23
Crystal system, space group	Orthorhombic, Iba2
Temperature (K)	294
a, b, c (Å)	10.679 (2), 22.431 (5), 7.1980 (14)
V (Å³)	1724.2 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.906, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	1587, 1432, 1369
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.120, 1.00
No. of reflections	1432
No. of parameters	111
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.35
Absolute structure	Flack (1983), 576 Friedel pairs
Absolute structure parameter	0.04 (14)

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2ⁱ	0.86	2.27	2.996 (4)	142
N1—H1C···O1ⁱⁱ	0.86	2.16	3.001 (4)	164
N2—H2C···O1ⁱⁱⁱ	0.86	2.60	3.278 (4)	137

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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