N-(2,4,6-Trimethyl­phen­yl)methane­sulfonamide

The structure of the title compound, C₁₀H₁₅NO₂S, resembles those of other methane­sulfonanilides, with similar geometric parameters except for some differences in the bond and torsion angles. The amide H atom lies on one side of the plane of the benzene ring, while the methane­sulfonyl group is on the opposite side of the plane, as in other methane­sulfonanilides. The amide H atom is thus available to a receptor mol­ecule during its biological activity. The mol­ecules are packed into polymeric chains in the direction of the b axis through N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](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

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S1. Comment

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).

Related literature

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).

S2. Experimental

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.

S3. Refinement

All H atoms attached were fixed geometrically and treated as riding on their parent atoms with C—H = 0.93 Å (C_aromatic) or 0.96 Å (CH₃) and N—H =0.86 Å with U_iso(H) = 1.2U_eq(C_aromatic or N) and U_iso(H) = 1.5U_eq(CH₃).

Computing details

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.

Figures

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view of the title compound showing the formation of chain parallel to the b axis through N—H···O hydrogen bonds axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry code: (i) x, y - 1, z].

N-(2,4,6-Trimethylphenyl)methanesulfonamide

Crystal data

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) Å^3	0.60 × 0.11 × 0.03 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.198	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1367P)^2] where P = (Fo^2 + 2Fc^2)/3
1953 reflections	(Δ/σ)max = 0.031
131 parameters	Δρmax = 0.84 e Å^−3
0 restraints	Δρmin = −0.55 e Å^−3

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
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)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O4^i	0.86	2.33	2.944 (4)	128

Symmetry code: (i) x, y−1, z.