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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1815.
Published online 2009 July 11. doi:  10.1107/S1600536809026142
PMCID: PMC2977214

5-Amino-2-methyl­benzene­sulfonamide

Abstract

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 [triangle]).

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Object name is e-65-o1815-scheme1.jpg

Experimental

Crystal data

  • C7H10N2O2S
  • M r = 186.23
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1815-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.120
  • S = 1.00
  • 1432 reflections
  • 111 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.35 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 576 Friedel pairs
  • Flack parameter: 0.04 (14)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

H atoms were positioned geometrically, with N-H = 0.86 Å (for NH2) and C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Figures

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.

Crystal data

C7H10N2O2SF(000) = 784
Mr = 186.23Dx = 1.435 Mg m3
Orthorhombic, Iba2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2cCell parameters from 25 reflections
a = 10.679 (2) Åθ = 10–14°
b = 22.431 (5) ŵ = 0.34 mm1
c = 7.1980 (14) ÅT = 294 K
V = 1724.2 (6) Å3Block, colorless
Z = 80.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer1369 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
graphiteθmax = 25.3°, θmin = 1.8°
ω/2θ scansh = −12→0
Absorption correction: ψ scan (North et al., 1968)k = −26→8
Tmin = 0.906, Tmax = 0.967l = −8→8
1587 measured reflections3 standard reflections every 120 min
1432 independent reflections intensity decay: 1%

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040w = 1/[σ2(Fo2) + (0.1P)2 + 0.35P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.28 e Å3
1432 reflectionsΔρmin = −0.35 e Å3
111 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.019 (2)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 576 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.04 (14)

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 (Å2)

xyzUiso*/Ueq
S0.16988 (6)0.09021 (3)0.64671 (14)0.0332 (3)
O10.06327 (19)0.12096 (9)0.5690 (4)0.0469 (6)
N10.1216 (3)0.05631 (12)0.8282 (5)0.0495 (8)
H1B0.13620.01890.84190.059*
H1C0.08100.07550.91230.059*
C10.4280 (3)0.06855 (16)0.8644 (6)0.0527 (9)
H1D0.51270.06860.90890.079*
H1E0.42100.04200.76040.079*
H1F0.37300.05550.96180.079*
O20.2333 (2)0.04672 (10)0.5348 (4)0.0511 (7)
N20.3024 (3)0.30886 (10)0.6676 (5)0.0489 (8)
H2B0.23290.31690.61250.059*
H2C0.35320.33720.69620.059*
C20.3922 (2)0.13040 (13)0.8053 (4)0.0316 (6)
C30.2794 (2)0.14549 (11)0.7132 (4)0.0272 (6)
C40.2507 (2)0.20373 (11)0.6649 (5)0.0287 (6)
H4A0.17670.21180.60170.034*
C50.3323 (3)0.25064 (13)0.7103 (5)0.0318 (7)
C60.4439 (3)0.23609 (14)0.8042 (5)0.0357 (7)
H6A0.49970.26620.83670.043*
C70.4711 (3)0.17810 (14)0.8483 (4)0.0363 (7)
H7A0.54580.17010.90980.044*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S0.0294 (4)0.0314 (4)0.0390 (5)−0.0021 (2)−0.0014 (3)−0.0050 (3)
O10.0350 (11)0.0441 (12)0.0615 (15)−0.0049 (10)−0.0151 (11)0.0014 (11)
N10.0459 (16)0.0367 (14)0.066 (2)0.0010 (12)0.0155 (16)0.0131 (13)
C10.0487 (19)0.0423 (17)0.067 (2)0.0114 (15)−0.016 (2)0.0051 (18)
O20.0447 (14)0.0482 (13)0.0603 (17)−0.0016 (10)0.0036 (12)−0.0242 (12)
N20.0561 (15)0.0312 (12)0.059 (2)−0.0070 (11)−0.0146 (18)0.0069 (14)
C20.0283 (14)0.0348 (15)0.0317 (15)0.0046 (11)0.0002 (12)−0.0003 (11)
C30.0236 (12)0.0307 (13)0.0273 (13)0.0010 (10)0.0024 (11)−0.0021 (11)
C40.0249 (12)0.0330 (13)0.0281 (15)−0.0009 (10)−0.0035 (12)0.0019 (11)
C50.0374 (14)0.0322 (14)0.0258 (14)0.0000 (10)0.0029 (12)0.0010 (11)
C60.0309 (13)0.0422 (16)0.0339 (15)−0.0101 (12)−0.0014 (13)−0.0054 (13)
C70.0248 (14)0.0503 (17)0.0338 (16)0.0022 (11)−0.0052 (12)−0.0034 (11)

Geometric parameters (Å, °)

S—O21.435 (2)N2—H2B0.8600
S—O11.444 (2)N2—H2C0.8600
S—N11.597 (3)C2—C71.397 (4)
S—C31.770 (3)C2—C31.416 (4)
N1—H1B0.8600C3—C41.386 (4)
N1—H1C0.8600C4—C51.405 (4)
C1—C21.501 (4)C4—H4A0.9300
C1—H1D0.9600C5—C61.408 (4)
C1—H1E0.9600C6—C71.370 (5)
C1—H1F0.9600C6—H6A0.9300
N2—C51.379 (4)C7—H7A0.9300
O2—S—O1118.64 (18)C7—C2—C3115.7 (3)
O2—S—N1106.75 (16)C7—C2—C1119.5 (3)
O1—S—N1106.85 (15)C3—C2—C1124.8 (3)
O2—S—C3108.43 (14)C4—C3—C2122.1 (2)
O1—S—C3106.92 (12)C4—C3—S116.5 (2)
N1—S—C3108.98 (17)C2—C3—S121.4 (2)
S—N1—H1B120.0C3—C4—C5120.7 (3)
S—N1—H1C120.0C3—C4—H4A119.7
H1B—N1—H1C120.0C5—C4—H4A119.7
C2—C1—H1D109.5N2—C5—C4120.9 (3)
C2—C1—H1E109.5N2—C5—C6121.5 (3)
H1D—C1—H1E109.5C4—C5—C6117.6 (3)
C2—C1—H1F109.5C7—C6—C5120.7 (3)
H1D—C1—H1F109.5C7—C6—H6A119.7
H1E—C1—H1F109.5C5—C6—H6A119.7
C5—N2—H2B120.0C6—C7—C2123.3 (3)
C5—N2—H2C120.0C6—C7—H7A118.4
H2B—N2—H2C120.0C2—C7—H7A118.4
C7—C2—C3—C41.5 (5)C2—C3—C4—C5−1.6 (5)
C1—C2—C3—C4178.9 (3)S—C3—C4—C5−179.5 (2)
C7—C2—C3—S179.3 (2)C3—C4—C5—N2−177.9 (3)
C1—C2—C3—S−3.3 (5)C3—C4—C5—C60.7 (5)
O2—S—C3—C4123.0 (3)N2—C5—C6—C7178.9 (3)
O1—S—C3—C4−6.0 (3)C4—C5—C6—C70.3 (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—C2176.1 (3)C1—C2—C7—C6−178.1 (3)
N1—S—C3—C261.0 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···O2i0.862.272.996 (4)142
N1—H1C···O1ii0.862.163.001 (4)164
N2—H2C···O1iii0.862.603.278 (4)137

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2722).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography