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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030437/bt2408sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030437/bt2408Isup2.hkl |
CCDC reference: 655046
The title compound was prepared according to the literature method (Jayalakshmi & Gowda, 2004). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Jayalakshmi & Gowda, 2004). Single crystals of the compound were obtained by slow evaporation of an ethanolic solution.
The methyl H atoms were positioned with idealized geometry using a riding model with C—H = 0.96 Å. The other H atoms were located in difference map, and their positional parameters were refined freely [N—H = 0.90 (3) Å, and C—H = 0.89 (4)–0.99 (3) Å]. Uiso(H) values were set equal to 1.2 Ueq of the parent atom.
The biological activity of sulfonanilides is thought to be due to the amide hydrogen portion of the molecules as it can align itself in relation to a receptor site. Thus the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(3,5-dimethylphenyl)- methanesulfonamide has been determined as part of our study of the substituent effects on the solid state structures of methanesulfonanilides (Gowda et al., 2007a, Gowda et al., 2007b, Gowda et al., 2007c, Gowda et al., 2007d, Gowda et al., 2007e). The structure of the title compound (Fig. 1) is similar to those of N-(phenyl)- methanesulfonamide (Klug, 1968), N-(3-methylphenyl)- methanesulfonamide (Gowda et al., 2007a), N-(3,5-dichlorophenyl)-methanesulfonamide (Gowda et al., 2007e) and other methanesulfonanilides (Gowda et al., 2007b, c, d), with similar geometric parameters. The substitution of a methyl group at the meta position of PMSA (Klug, 1968) to produce 3MPMSA changes its space group from monoclinic P21/c to orthorhombic Pccn (Gowda et al., 2007a). The N—H···O hydrogen bonds (Table 1) build up centrosymmetric dimers (Fig. 2).
For related literature, see: Gowda et al. (2007a,b, c,d,e); Jayalakshmi & Gowda (2004); Klug (1968).
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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C9H13NO2S | F(000) = 424 |
Mr = 199.26 | Dx = 1.324 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 16.273 (2) Å | θ = 7.3–37.0° |
b = 5.1208 (7) Å | µ = 2.63 mm−1 |
c = 12.105 (1) Å | T = 299 K |
β = 97.84 (1)° | Long plate, colourless |
V = 999.3 (2) Å3 | 0.60 × 0.35 × 0.03 mm |
Z = 4 |
Enraf-Nonius CAD-4 diffractometer | 1604 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 66.9°, θmin = 2.7° |
ω/2θ scans | h = −19→19 |
Absorption correction: psi-scan (North et al., 1968) | k = 0→6 |
Tmin = 0.395, Tmax = 0.922 | l = −14→2 |
2110 measured reflections | 3 standard reflections every 120 min |
1781 independent reflections | intensity decay: 1.0% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.172 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1338P)2 + 0.2826P] where P = (Fo2 + 2Fc2)/3 |
1781 reflections | (Δ/σ)max = 0.009 |
133 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.85 e Å−3 |
C9H13NO2S | V = 999.3 (2) Å3 |
Mr = 199.26 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 16.273 (2) Å | µ = 2.63 mm−1 |
b = 5.1208 (7) Å | T = 299 K |
c = 12.105 (1) Å | 0.60 × 0.35 × 0.03 mm |
β = 97.84 (1)° |
Enraf-Nonius CAD-4 diffractometer | 1604 reflections with I > 2σ(I) |
Absorption correction: psi-scan (North et al., 1968) | Rint = 0.041 |
Tmin = 0.395, Tmax = 0.922 | 3 standard reflections every 120 min |
2110 measured reflections | intensity decay: 1.0% |
1781 independent reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.172 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.57 e Å−3 |
1781 reflections | Δρmin = −0.85 e Å−3 |
133 parameters |
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 | ||
C1 | 0.39578 (17) | 0.3450 (5) | −0.0116 (2) | 0.0410 (6) | |
H1A | 0.3368 | 0.3475 | −0.0333 | 0.049* | |
H1B | 0.4218 | 0.2603 | −0.0685 | 0.049* | |
H1C | 0.4160 | 0.5208 | −0.0020 | 0.049* | |
C6 | 0.29375 (14) | 0.3915 (5) | 0.20981 (18) | 0.0323 (5) | |
C7 | 0.27426 (16) | 0.5821 (5) | 0.2837 (2) | 0.0386 (6) | |
H7 | 0.315 (2) | 0.670 (6) | 0.325 (3) | 0.046* | |
C8 | 0.19292 (18) | 0.6424 (5) | 0.2932 (2) | 0.0433 (7) | |
C9 | 0.13008 (16) | 0.5109 (6) | 0.2254 (3) | 0.0495 (7) | |
H9 | 0.071 (2) | 0.556 (7) | 0.231 (3) | 0.059* | |
C10 | 0.14826 (17) | 0.3211 (5) | 0.1507 (3) | 0.0450 (7) | |
C11 | 0.23041 (15) | 0.2584 (6) | 0.1435 (2) | 0.0390 (6) | |
H11 | 0.2410 (19) | 0.125 (7) | 0.097 (3) | 0.047* | |
C12 | 0.1731 (2) | 0.8452 (7) | 0.3755 (3) | 0.0632 (9) | |
H12A | 0.1140 | 0.8615 | 0.3719 | 0.076* | |
H12B | 0.1962 | 1.0100 | 0.3579 | 0.076* | |
H12C | 0.1965 | 0.7934 | 0.4494 | 0.076* | |
C13 | 0.0797 (2) | 0.1815 (8) | 0.0764 (4) | 0.0688 (11) | |
H13A | 0.0319 | 0.2927 | 0.0634 | 0.083* | |
H13B | 0.0655 | 0.0237 | 0.1122 | 0.083* | |
H13C | 0.0983 | 0.1395 | 0.0066 | 0.083* | |
N5 | 0.37874 (13) | 0.3388 (4) | 0.20790 (17) | 0.0345 (5) | |
H5N | 0.4167 (18) | 0.451 (6) | 0.242 (3) | 0.041* | |
O3 | 0.38043 (13) | −0.0767 (3) | 0.10100 (19) | 0.0510 (5) | |
O4 | 0.50638 (11) | 0.1894 (4) | 0.14746 (16) | 0.0425 (5) | |
S2 | 0.41901 (3) | 0.17442 (10) | 0.11399 (4) | 0.0314 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0492 (15) | 0.0395 (15) | 0.0339 (12) | 0.0009 (11) | 0.0045 (10) | 0.0027 (10) |
C6 | 0.0348 (11) | 0.0303 (12) | 0.0322 (11) | −0.0031 (10) | 0.0059 (9) | 0.0019 (9) |
C7 | 0.0417 (13) | 0.0323 (13) | 0.0424 (13) | −0.0055 (10) | 0.0076 (10) | −0.0028 (10) |
C8 | 0.0470 (15) | 0.0312 (14) | 0.0548 (16) | −0.0005 (11) | 0.0176 (12) | −0.0004 (11) |
C9 | 0.0373 (13) | 0.0450 (16) | 0.0679 (18) | 0.0012 (12) | 0.0135 (12) | −0.0002 (14) |
C10 | 0.0352 (13) | 0.0448 (17) | 0.0545 (16) | −0.0063 (11) | 0.0038 (11) | 0.0000 (12) |
C11 | 0.0392 (13) | 0.0360 (13) | 0.0417 (13) | −0.0066 (11) | 0.0057 (10) | −0.0069 (12) |
C12 | 0.066 (2) | 0.050 (2) | 0.080 (2) | 0.0001 (15) | 0.0325 (18) | −0.0163 (16) |
C13 | 0.0410 (15) | 0.074 (3) | 0.088 (3) | −0.0103 (15) | −0.0026 (15) | −0.0183 (19) |
N5 | 0.0334 (10) | 0.0351 (12) | 0.0348 (10) | −0.0034 (8) | 0.0038 (8) | −0.0058 (8) |
O3 | 0.0642 (13) | 0.0204 (10) | 0.0702 (13) | −0.0042 (8) | 0.0153 (9) | −0.0027 (8) |
O4 | 0.0390 (11) | 0.0408 (11) | 0.0486 (11) | 0.0099 (7) | 0.0089 (8) | 0.0058 (8) |
S2 | 0.0361 (4) | 0.0226 (4) | 0.0361 (4) | 0.00312 (19) | 0.0064 (3) | 0.00110 (19) |
C1—S2 | 1.750 (2) | C10—C11 | 1.389 (4) |
C1—H1A | 0.9600 | C10—C13 | 1.513 (4) |
C1—H1B | 0.9600 | C11—H11 | 0.92 (3) |
C1—H1C | 0.9600 | C12—H12A | 0.9600 |
C6—C7 | 1.390 (4) | C12—H12B | 0.9600 |
C6—C11 | 1.395 (4) | C12—H12C | 0.9600 |
C6—N5 | 1.412 (3) | C13—H13A | 0.9600 |
C7—C8 | 1.379 (4) | C13—H13B | 0.9600 |
C7—H7 | 0.89 (4) | C13—H13C | 0.9600 |
C8—C9 | 1.394 (4) | N5—S2 | 1.623 (2) |
C8—C12 | 1.505 (4) | N5—H5N | 0.90 (3) |
C9—C10 | 1.387 (4) | O3—S2 | 1.4300 (19) |
C9—H9 | 0.99 (3) | O4—S2 | 1.4262 (19) |
S2—C1—H1A | 109.5 | C6—C11—H11 | 122.1 (19) |
S2—C1—H1B | 109.5 | C8—C12—H12A | 109.5 |
H1A—C1—H1B | 109.5 | C8—C12—H12B | 109.5 |
S2—C1—H1C | 109.5 | H12A—C12—H12B | 109.5 |
H1A—C1—H1C | 109.5 | C8—C12—H12C | 109.5 |
H1B—C1—H1C | 109.5 | H12A—C12—H12C | 109.5 |
C7—C6—C11 | 119.9 (2) | H12B—C12—H12C | 109.5 |
C7—C6—N5 | 117.0 (2) | C10—C13—H13A | 109.5 |
C11—C6—N5 | 123.1 (2) | C10—C13—H13B | 109.5 |
C8—C7—C6 | 121.1 (2) | H13A—C13—H13B | 109.5 |
C8—C7—H7 | 119 (2) | C10—C13—H13C | 109.5 |
C6—C7—H7 | 120 (2) | H13A—C13—H13C | 109.5 |
C7—C8—C9 | 118.6 (3) | H13B—C13—H13C | 109.5 |
C7—C8—C12 | 120.3 (3) | C6—N5—S2 | 126.90 (17) |
C9—C8—C12 | 121.1 (3) | C6—N5—H5N | 118.8 (19) |
C10—C9—C8 | 121.2 (2) | S2—N5—H5N | 109.6 (19) |
C10—C9—H9 | 120 (2) | O4—S2—O3 | 119.03 (11) |
C8—C9—H9 | 119 (2) | O4—S2—N5 | 104.79 (11) |
C9—C10—C11 | 119.7 (2) | O3—S2—N5 | 109.27 (12) |
C9—C10—C13 | 120.9 (3) | O4—S2—C1 | 107.99 (12) |
C11—C10—C13 | 119.4 (3) | O3—S2—C1 | 108.29 (13) |
C10—C11—C6 | 119.5 (3) | N5—S2—C1 | 106.85 (12) |
C10—C11—H11 | 118.3 (19) | ||
C11—C6—C7—C8 | 0.2 (4) | C13—C10—C11—C6 | 178.4 (3) |
N5—C6—C7—C8 | −178.5 (2) | C7—C6—C11—C10 | 1.0 (4) |
C6—C7—C8—C9 | −1.1 (4) | N5—C6—C11—C10 | 179.7 (2) |
C6—C7—C8—C12 | 178.6 (3) | C7—C6—N5—S2 | −166.20 (19) |
C7—C8—C9—C10 | 0.7 (4) | C11—C6—N5—S2 | 15.1 (3) |
C12—C8—C9—C10 | −179.0 (3) | C6—N5—S2—O4 | 177.13 (19) |
C8—C9—C10—C11 | 0.5 (4) | C6—N5—S2—O3 | −54.3 (2) |
C8—C9—C10—C13 | −179.3 (3) | C6—N5—S2—C1 | 62.7 (2) |
C9—C10—C11—C6 | −1.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O4i | 0.90 (3) | 2.10 (3) | 2.982 (3) | 168 (3) |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C9H13NO2S |
Mr | 199.26 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 299 |
a, b, c (Å) | 16.273 (2), 5.1208 (7), 12.105 (1) |
β (°) | 97.84 (1) |
V (Å3) | 999.3 (2) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.63 |
Crystal size (mm) | 0.60 × 0.35 × 0.03 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 |
Absorption correction | Psi-scan (North et al., 1968) |
Tmin, Tmax | 0.395, 0.922 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2110, 1781, 1604 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.172, 1.06 |
No. of reflections | 1781 |
No. of parameters | 133 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.57, −0.85 |
Computer programs: CAD-4-PC (Enraf-Nonius, 1996), CAD-4-PC, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O4i | 0.90 (3) | 2.10 (3) | 2.982 (3) | 168 (3) |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
The biological activity of sulfonanilides is thought to be due to the amide hydrogen portion of the molecules as it can align itself in relation to a receptor site. Thus the structural studies of sulfonanilides are of interest. In the present work, the structure of N-(3,5-dimethylphenyl)- methanesulfonamide has been determined as part of our study of the substituent effects on the solid state structures of methanesulfonanilides (Gowda et al., 2007a, Gowda et al., 2007b, Gowda et al., 2007c, Gowda et al., 2007d, Gowda et al., 2007e). The structure of the title compound (Fig. 1) is similar to those of N-(phenyl)- methanesulfonamide (Klug, 1968), N-(3-methylphenyl)- methanesulfonamide (Gowda et al., 2007a), N-(3,5-dichlorophenyl)-methanesulfonamide (Gowda et al., 2007e) and other methanesulfonanilides (Gowda et al., 2007b, c, d), with similar geometric parameters. The substitution of a methyl group at the meta position of PMSA (Klug, 1968) to produce 3MPMSA changes its space group from monoclinic P21/c to orthorhombic Pccn (Gowda et al., 2007a). The N—H···O hydrogen bonds (Table 1) build up centrosymmetric dimers (Fig. 2).