2-Amino-4-methyl­benzene­sulfonamide

Abstract

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,

• a = 9.873 (5) Å

• b = 9.151 (4) Å

• c = 10.408 (5) Å

• β = 114.689 (6)°

• V = 854.4 (7) ų

• 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[F ² > 2σ(F ²)] = 0.047

• wR(F ²) = 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

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.

Supplementary Material

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

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) ; (ii) .

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All the H atoms attached to C atoms were placed in geometrical positions and constrained to ride on their parent atoms with C—H distance in the range 0.93–0.98 Å, They were treated as riding atoms, with U_iso(H) = 1.2U_eq(C).

Figures

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.

Crystal data

C7H10N2O2S	F(000) = 392
Mr = 186.23	Dx = 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

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

Refinement

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(Fo2) + (0.0721P)2 + 0.701P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
1449 reflections	Δρmax = 0.56 e Å−3
110 parameters	Δρmin = −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)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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.