Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025883/dn2182sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025883/dn2182Isup2.hkl |
CCDC reference: 614677
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.006 Å
- R factor = 0.069
- wR factor = 0.198
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT149_ALERT_3_B su on the beta Angle is Too Large (x 100) .. 9 Deg.
Alert level C CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 10.16 Cell volume su given = 8.00 RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.114 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.93 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S2 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT415_ALERT_2_C Short Inter D-H..H-X H5 .. H14C .. 2.13 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.933 Tmax scaled 0.930 Tmin scaled 0.654
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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 title compound were obtained from a slow evaporation of its ethanolic solution and used for X-ray diffraction studied at room temperature.
All H atoms attached were fixed geometrically and treated as riding on their parent atoms with C—H = 0.93 Å (Caromatic) or 0.96 Å (CH3) and N—H =0.86 Å with Uiso(H) = 1.2Ueq(Caromatic or N) and Uiso(H) = 1.5Ueq(CH3).
The biological activity of alkyl sulphonanilides is thought to be due to the hydrogen of the phenyl N—H portion of the sulphonanilide molecules as it can align itself, in relation to a receptor site. Therefore the structural studies of sulphonanilides are of interest. In the present work, the structure of N-(2,4,6-trimethylphenyl)-methanesulfonamde (246TMPMSA) has been determined to explore the substituent effects on the solid state structures of sulfonanilides (Gowda et al., 2007a,b,c,d,e,f,g,h,i,j,k,l,m,n). The structure of 246TMPMSA (Fig. 1) resembles those of N-(phenyl)-methanesulfonamde (PMSA) (Klug, 1968), N-(2-methylphenyl)-methanesulphonamde (2MPMSA), N-(4-methylphenyl)-methanesulfonamde (4MPMSA), N-(2,4-dimethylphenyl)-methanesulfonamde (24DMPMSA), N-(2,6-dimethylphenyl)-methanesulfonamde (26DMPMSA) and other methanesulfonanilides (Gowda et al.,2007a,b,c,d,e,f,g,h,i,j,k, l,m,n). The ortho substitution of a methyl group in PMSA changes its space group from monoclinic P21/c (Klug, 1968) to triclinic P-1 (Gowda et al., 2007d). The substitution of an additional methyl group at the second ortho position in 2MPMSA to produce 26DMPMSA changes the space group from triclinic P-1 to orthorhombic P212121, determined under identical conditions (Gowda et al., 2007n). Introduction of the third methyl group at the para position of 26DMPMSA to produce 246TMPMSA changes the space group from orthorhombic P212121 to monoclinic P21/n. The geometric parameters in 246TMPMSA are similar to those in PMSA, 2MPMSA, 4MPMSA, 24DMPMSA, 26DMPMSA and other methanesulfonanilides (Gowda et al., 2007a-n), except for some difference in the bond and torsional angles. The amide hydrogen sits alone on one side of the plane of the phenyl group, while the whole methanesulfonyl group is on the opposite side of the plane, similar to that in other methanesulfonanilides. The amide hydrogen is thus available to a receptor molecule during its biological activity. The molecules in 246TMPMSA are packed into polymeric chain in the direction of b axis through N—H···O hydrogen bonds (Fig. 2, Table 1).
For related literature, see: Gowda et al. (2007a, b,c,d,e, f,g,h,i,j, k,l,m,n); 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: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'; software used to prepare material for publication: SHELXL97.
C10H15NO2S | F(000) = 456 |
Mr = 213.29 | Dx = 1.295 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 14.588 (4) Å | θ = 7.0–19.1° |
b = 4.920 (2) Å | µ = 2.43 mm−1 |
c = 16.386 (8) Å | T = 299 K |
β = 111.49 (9)° | Needle, colourless |
V = 1094.3 (8) Å3 | 0.60 × 0.11 × 0.03 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1385 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.114 |
Graphite monochromator | θmax = 67.0°, θmin = 3.5° |
ω/θ scans | h = −17→2 |
Absorption correction: psi-scan (North et al., 1968) | k = 0→5 |
Tmin = 0.701, Tmax = 0.996 | l = −18→19 |
2261 measured reflections | 3 standard reflections every 120 min |
1953 independent reflections | intensity decay: 1.2% |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.1367P)2] where P = (Fo2 + 2Fc2)/3 |
1953 reflections | (Δ/σ)max = 0.031 |
131 parameters | Δρmax = 0.84 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
C10H15NO2S | V = 1094.3 (8) Å3 |
Mr = 213.29 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 14.588 (4) Å | µ = 2.43 mm−1 |
b = 4.920 (2) Å | T = 299 K |
c = 16.386 (8) Å | 0.60 × 0.11 × 0.03 mm |
β = 111.49 (9)° |
Enraf–Nonius CAD-4 diffractometer | 1385 reflections with I > 2σ(I) |
Absorption correction: psi-scan (North et al., 1968) | Rint = 0.114 |
Tmin = 0.701, Tmax = 0.996 | 3 standard reflections every 120 min |
2261 measured reflections | intensity decay: 1.2% |
1953 independent reflections |
R[F2 > 2σ(F2)] = 0.069 | 0 restraints |
wR(F2) = 0.198 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.84 e Å−3 |
1953 reflections | Δρmin = −0.55 e Å−3 |
131 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 | 0.1583 (3) | −0.1041 (11) | 0.1477 (3) | 0.0605 (12) | |
H1A | 0.1547 | −0.2978 | 0.1528 | 0.091* | |
H1B | 0.1020 | −0.0415 | 0.0993 | 0.091* | |
H1C | 0.1590 | −0.0197 | 0.2008 | 0.091* | |
C6 | 0.2181 (3) | −0.0825 (7) | −0.0439 (2) | 0.0366 (8) | |
C7 | 0.1251 (3) | −0.1758 (7) | −0.0963 (2) | 0.0395 (9) | |
C8 | 0.0818 (3) | −0.0731 (8) | −0.1804 (2) | 0.0455 (9) | |
H8 | 0.0206 | −0.1397 | −0.2163 | 0.055* | |
C9 | 0.1265 (3) | 0.1260 (9) | −0.2131 (2) | 0.0487 (10) | |
C10 | 0.2200 (3) | 0.2072 (10) | −0.1605 (3) | 0.0489 (10) | |
H10 | 0.2523 | 0.3342 | −0.1824 | 0.059* | |
C11 | 0.2685 (3) | 0.1074 (8) | −0.0758 (2) | 0.0408 (9) | |
C12 | 0.0716 (3) | −0.3944 (9) | −0.0663 (3) | 0.0541 (11) | |
H12A | 0.0219 | −0.4751 | −0.1164 | 0.081* | |
H12B | 0.0412 | −0.3153 | −0.0289 | 0.081* | |
H12C | 0.1177 | −0.5314 | −0.0344 | 0.081* | |
C13 | 0.0751 (4) | 0.2409 (12) | −0.3028 (3) | 0.0710 (14) | |
H13A | 0.0371 | 0.3965 | −0.2991 | 0.107* | |
H13B | 0.0322 | 0.1058 | −0.3396 | 0.107* | |
H13C | 0.1229 | 0.2943 | −0.3272 | 0.107* | |
C14 | 0.3723 (3) | 0.1976 (10) | −0.0241 (3) | 0.0567 (11) | |
H14A | 0.4035 | 0.2541 | −0.0637 | 0.085* | |
H14B | 0.4086 | 0.0493 | 0.0112 | 0.085* | |
H14C | 0.3710 | 0.3469 | 0.0132 | 0.085* | |
N5 | 0.2665 (2) | −0.1810 (6) | 0.04429 (19) | 0.0405 (8) | |
H5 | 0.2971 | −0.3338 | 0.0518 | 0.049* | |
O3 | 0.3461 (2) | −0.1205 (6) | 0.20308 (18) | 0.0558 (8) | |
O4 | 0.2624 (3) | 0.2640 (6) | 0.1099 (2) | 0.0637 (10) | |
S2 | 0.26621 (7) | −0.01834 (17) | 0.12998 (5) | 0.0394 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.067 (3) | 0.066 (3) | 0.057 (3) | −0.002 (2) | 0.033 (2) | −0.007 (2) |
C6 | 0.048 (2) | 0.0289 (17) | 0.0370 (17) | 0.0049 (15) | 0.0202 (16) | 0.0029 (14) |
C7 | 0.050 (2) | 0.0295 (19) | 0.044 (2) | −0.0014 (15) | 0.0229 (17) | −0.0048 (15) |
C8 | 0.044 (2) | 0.049 (2) | 0.0422 (19) | 0.0018 (17) | 0.0133 (16) | −0.0092 (18) |
C9 | 0.056 (2) | 0.055 (3) | 0.0374 (19) | 0.0074 (19) | 0.0198 (18) | −0.0003 (18) |
C10 | 0.059 (3) | 0.051 (2) | 0.044 (2) | 0.0020 (19) | 0.0288 (19) | 0.0101 (18) |
C11 | 0.045 (2) | 0.042 (2) | 0.0373 (18) | 0.0007 (16) | 0.0181 (16) | 0.0024 (16) |
C12 | 0.058 (3) | 0.046 (2) | 0.063 (3) | −0.0145 (19) | 0.027 (2) | −0.004 (2) |
C13 | 0.079 (3) | 0.087 (4) | 0.043 (2) | 0.020 (3) | 0.018 (2) | 0.012 (2) |
C14 | 0.052 (3) | 0.065 (3) | 0.056 (2) | −0.006 (2) | 0.024 (2) | 0.005 (2) |
N5 | 0.062 (2) | 0.0245 (15) | 0.0372 (16) | 0.0087 (13) | 0.0206 (14) | 0.0038 (12) |
O3 | 0.0647 (19) | 0.0549 (19) | 0.0417 (15) | 0.0019 (14) | 0.0122 (13) | 0.0032 (13) |
O4 | 0.128 (3) | 0.0200 (15) | 0.0497 (17) | 0.0024 (14) | 0.0397 (18) | 0.0021 (12) |
S2 | 0.0600 (6) | 0.0242 (5) | 0.0340 (5) | 0.0010 (4) | 0.0173 (4) | 0.0033 (3) |
C1—S2 | 1.754 (4) | C11—C14 | 1.506 (6) |
C1—H1A | 0.9600 | C12—H12A | 0.9600 |
C1—H1B | 0.9600 | C12—H12B | 0.9600 |
C1—H1C | 0.9600 | C12—H12C | 0.9600 |
C6—C7 | 1.391 (5) | C13—H13A | 0.9600 |
C6—C11 | 1.402 (5) | C13—H13B | 0.9600 |
C6—N5 | 1.440 (4) | C13—H13C | 0.9600 |
C7—C8 | 1.385 (5) | C14—H14A | 0.9600 |
C7—C12 | 1.513 (5) | C14—H14B | 0.9600 |
C8—C9 | 1.388 (6) | C14—H14C | 0.9600 |
C8—H8 | 0.9300 | N5—S2 | 1.618 (3) |
C9—C10 | 1.379 (6) | N5—H5 | 0.8600 |
C9—C13 | 1.494 (6) | O3—S2 | 1.422 (3) |
C10—C11 | 1.396 (5) | O4—S2 | 1.424 (3) |
C10—H10 | 0.9300 | ||
S2—C1—H1A | 109.5 | H12A—C12—H12B | 109.5 |
S2—C1—H1B | 109.5 | C7—C12—H12C | 109.5 |
H1A—C1—H1B | 109.5 | H12A—C12—H12C | 109.5 |
S2—C1—H1C | 109.5 | H12B—C12—H12C | 109.5 |
H1A—C1—H1C | 109.5 | C9—C13—H13A | 109.5 |
H1B—C1—H1C | 109.5 | C9—C13—H13B | 109.5 |
C7—C6—C11 | 121.1 (3) | H13A—C13—H13B | 109.5 |
C7—C6—N5 | 121.1 (3) | C9—C13—H13C | 109.5 |
C11—C6—N5 | 117.8 (3) | H13A—C13—H13C | 109.5 |
C8—C7—C6 | 118.7 (4) | H13B—C13—H13C | 109.5 |
C8—C7—C12 | 118.8 (4) | C11—C14—H14A | 109.5 |
C6—C7—C12 | 122.5 (3) | C11—C14—H14B | 109.5 |
C7—C8—C9 | 122.3 (4) | H14A—C14—H14B | 109.5 |
C7—C8—H8 | 118.9 | C11—C14—H14C | 109.5 |
C9—C8—H8 | 118.9 | H14A—C14—H14C | 109.5 |
C10—C9—C8 | 117.4 (4) | H14B—C14—H14C | 109.5 |
C10—C9—C13 | 122.1 (4) | C6—N5—S2 | 123.3 (3) |
C8—C9—C13 | 120.5 (4) | C6—N5—H5 | 118.4 |
C9—C10—C11 | 123.0 (4) | S2—N5—H5 | 118.4 |
C9—C10—H10 | 118.5 | O3—S2—O4 | 119.3 (2) |
C11—C10—H10 | 118.5 | O3—S2—N5 | 107.10 (19) |
C10—C11—C6 | 117.4 (4) | O4—S2—N5 | 107.14 (17) |
C10—C11—C14 | 119.7 (4) | O3—S2—C1 | 106.5 (2) |
C6—C11—C14 | 122.9 (3) | O4—S2—C1 | 108.1 (2) |
C7—C12—H12A | 109.5 | N5—S2—C1 | 108.3 (2) |
C7—C12—H12B | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···O4i | 0.86 | 2.33 | 2.944 (4) | 128 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C10H15NO2S |
Mr | 213.29 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 299 |
a, b, c (Å) | 14.588 (4), 4.920 (2), 16.386 (8) |
β (°) | 111.49 (9) |
V (Å3) | 1094.3 (8) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.43 |
Crystal size (mm) | 0.60 × 0.11 × 0.03 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | Psi-scan (North et al., 1968) |
Tmin, Tmax | 0.701, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2261, 1953, 1385 |
Rint | 0.114 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.198, 1.02 |
No. of reflections | 1953 |
No. of parameters | 131 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.84, −0.55 |
Computer programs: CAD-4-PC (Enraf–Nonius, 1996), CAD-4-PC, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)', SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···O4i | 0.86 | 2.33 | 2.944 (4) | 128.4 |
Symmetry code: (i) x, y−1, z. |
The biological activity of alkyl sulphonanilides is thought to be due to the hydrogen of the phenyl N—H portion of the sulphonanilide molecules as it can align itself, in relation to a receptor site. Therefore the structural studies of sulphonanilides are of interest. In the present work, the structure of N-(2,4,6-trimethylphenyl)-methanesulfonamde (246TMPMSA) has been determined to explore the substituent effects on the solid state structures of sulfonanilides (Gowda et al., 2007a,b,c,d,e,f,g,h,i,j,k,l,m,n). The structure of 246TMPMSA (Fig. 1) resembles those of N-(phenyl)-methanesulfonamde (PMSA) (Klug, 1968), N-(2-methylphenyl)-methanesulphonamde (2MPMSA), N-(4-methylphenyl)-methanesulfonamde (4MPMSA), N-(2,4-dimethylphenyl)-methanesulfonamde (24DMPMSA), N-(2,6-dimethylphenyl)-methanesulfonamde (26DMPMSA) and other methanesulfonanilides (Gowda et al.,2007a,b,c,d,e,f,g,h,i,j,k, l,m,n). The ortho substitution of a methyl group in PMSA changes its space group from monoclinic P21/c (Klug, 1968) to triclinic P-1 (Gowda et al., 2007d). The substitution of an additional methyl group at the second ortho position in 2MPMSA to produce 26DMPMSA changes the space group from triclinic P-1 to orthorhombic P212121, determined under identical conditions (Gowda et al., 2007n). Introduction of the third methyl group at the para position of 26DMPMSA to produce 246TMPMSA changes the space group from orthorhombic P212121 to monoclinic P21/n. The geometric parameters in 246TMPMSA are similar to those in PMSA, 2MPMSA, 4MPMSA, 24DMPMSA, 26DMPMSA and other methanesulfonanilides (Gowda et al., 2007a-n), except for some difference in the bond and torsional angles. The amide hydrogen sits alone on one side of the plane of the phenyl group, while the whole methanesulfonyl group is on the opposite side of the plane, similar to that in other methanesulfonanilides. The amide hydrogen is thus available to a receptor molecule during its biological activity. The molecules in 246TMPMSA are packed into polymeric chain in the direction of b axis through N—H···O hydrogen bonds (Fig. 2, Table 1).