2,2-Dimethyl-N-(2-methyl-phenyl-sulfon-yl)propanamide.

In the title compound, C(12)H(17)NO(3)S, the amide H atom is syn to the ortho-methyl group of the benzene ring and the C-S-N-C torsion angle is -65.39 (17)°. The crystal structure features inversion-related dimers linked by pairs of N-H⋯O hydrogen bonds in which the acceptor O atom is bound to the S atom.

Related literature

Sulfonamide drugs contain the sulfanilamide moiety (Maren, 1976 ▶). Their tendency and preferences for hydrogen bonding in the solid state can give rise to polymorphism, see: Yang & Guillory (1972 ▶); Adsmond & Grant (2001 ▶). For our studies on the effect of substituents on the crystal structures of this class of compounds, see: Gowda et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C12H17NO3S

M = 255.33

Monoclinic,

a = 7.3827 (6) Å

b = 21.986 (2) Å

c = 8.6060 (8) Å

β = 97.158 (9)°

V = 1386.0 (2) Å3

Z = 4

Cu Kα radiation

μ = 2.06 mm−1

T = 299 K

0.30 × 0.25 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

3884 measured reflections

2472 independent reflections

2202 reflections with I > 2σ(I)

R int = 0.050

3 standard reflections every 120 min intensity decay: 0.5%

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.05

2472 reflections

162 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.35 e Å−3

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, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003400/tk2712sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003400/tk2712Isup2.hkl

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

C12H17NO3S	F(000) = 544
Mr = 255.33	Dx = 1.224 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 7.3827 (6) Å	θ = 6.0–21.6°
b = 21.986 (2) Å	µ = 2.06 mm−1
c = 8.6060 (8) Å	T = 299 K
β = 97.158 (9)°	Prism, red
V = 1386.0 (2) Å3	0.30 × 0.25 × 0.25 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.050
Radiation source: fine-focus sealed tube	θmax = 67.0°, θmin = 4.0°
graphite	h = −8→4
ω/2θ scans	k = −26→0
3884 measured reflections	l = −10→10
2472 independent reflections	3 standard reflections every 120 min
2202 reflections with I > 2σ(I)	intensity decay: 0.5%

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.5143P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2472 reflections	Δρmax = 0.38 e Å−3
162 parameters	Δρmin = −0.35 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0174 (8)

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	0.5655 (2)	0.64776 (8)	0.66047 (17)	0.0386 (4)
C2	0.7426 (2)	0.64421 (9)	0.6175 (2)	0.0460 (4)
C3	0.8623 (3)	0.69061 (10)	0.6714 (2)	0.0574 (5)
H3	0.9803	0.6902	0.6443	0.069*
C4	0.8114 (3)	0.73713 (10)	0.7636 (3)	0.0643 (6)
H4	0.8957	0.7669	0.7998	0.077*
C5	0.6366 (3)	0.73991 (10)	0.8024 (3)	0.0637 (6)
H5	0.6026	0.7715	0.8644	0.076*
C6	0.5122 (3)	0.69569 (9)	0.7493 (2)	0.0495 (4)
H6	0.3928	0.6979	0.7728	0.059*
C7	0.2796 (2)	0.62930 (9)	0.32969 (19)	0.0452 (4)
C8	0.2533 (3)	0.61352 (10)	0.1557 (2)	0.0574 (5)
C9	0.4402 (4)	0.60025 (15)	0.1019 (3)	0.0859 (9)
H9A	0.4938	0.5654	0.1569	0.103*
H9B	0.5187	0.6348	0.1237	0.103*
H9C	0.4248	0.5922	−0.0087	0.103*
C10	0.1352 (5)	0.55743 (18)	0.1291 (3)	0.1121 (12)
H10A	0.0191	0.5649	0.1648	0.135*
H10B	0.1942	0.5239	0.1861	0.135*
H10C	0.1173	0.5479	0.0193	0.135*
C11	0.1705 (5)	0.66816 (14)	0.0647 (3)	0.0888 (9)
H11A	0.2493	0.7027	0.0855	0.107*
H11B	0.0532	0.6770	0.0965	0.107*
H11C	0.1566	0.6592	−0.0453	0.107*
C12	0.8070 (3)	0.59462 (12)	0.5168 (3)	0.0670 (6)
H12A	0.7316	0.5940	0.4175	0.080*
H12B	0.7990	0.5561	0.5679	0.080*
H12C	0.9314	0.6022	0.5008	0.080*
N1	0.3642 (2)	0.58401 (7)	0.42600 (16)	0.0439 (4)
H1N	0.403 (3)	0.5529 (8)	0.390 (2)	0.053*
O1	0.49106 (18)	0.53203 (6)	0.66336 (13)	0.0508 (3)
O2	0.24290 (17)	0.60428 (7)	0.68099 (15)	0.0536 (4)
O3	0.2347 (2)	0.67637 (7)	0.38512 (15)	0.0604 (4)
S1	0.40583 (5)	0.588952 (19)	0.61796 (4)	0.03927 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0424 (9)	0.0401 (9)	0.0319 (7)	0.0023 (7)	−0.0013 (6)	0.0018 (6)
C2	0.0418 (9)	0.0505 (10)	0.0441 (9)	0.0040 (8)	−0.0020 (7)	0.0020 (8)
C3	0.0455 (10)	0.0631 (13)	0.0613 (12)	−0.0043 (9)	−0.0029 (9)	0.0057 (9)
C4	0.0690 (14)	0.0542 (12)	0.0650 (13)	−0.0143 (10)	−0.0107 (10)	−0.0032 (10)
C5	0.0817 (15)	0.0485 (12)	0.0588 (12)	−0.0006 (10)	0.0006 (11)	−0.0143 (9)
C6	0.0556 (10)	0.0488 (10)	0.0438 (9)	0.0043 (8)	0.0049 (8)	−0.0049 (8)
C7	0.0458 (9)	0.0525 (11)	0.0360 (8)	0.0026 (8)	−0.0005 (7)	0.0001 (7)
C8	0.0759 (13)	0.0610 (13)	0.0325 (9)	0.0066 (11)	−0.0040 (8)	−0.0011 (8)
C9	0.113 (2)	0.102 (2)	0.0456 (12)	0.0371 (17)	0.0222 (13)	0.0108 (12)
C10	0.145 (3)	0.113 (3)	0.0665 (16)	−0.038 (2)	−0.0314 (17)	−0.0137 (16)
C11	0.122 (2)	0.098 (2)	0.0431 (11)	0.0481 (18)	−0.0054 (12)	0.0072 (11)
C12	0.0462 (11)	0.0754 (16)	0.0807 (15)	0.0058 (10)	0.0127 (10)	−0.0192 (12)
N1	0.0523 (9)	0.0455 (9)	0.0321 (7)	0.0068 (7)	−0.0017 (6)	−0.0044 (6)
O1	0.0696 (8)	0.0416 (7)	0.0393 (6)	0.0031 (6)	−0.0009 (6)	0.0037 (5)
O2	0.0457 (7)	0.0712 (9)	0.0455 (7)	−0.0024 (6)	0.0112 (5)	−0.0053 (6)
O3	0.0777 (10)	0.0550 (8)	0.0466 (7)	0.0184 (7)	0.0007 (6)	−0.0044 (6)
S1	0.0434 (3)	0.0433 (3)	0.0304 (2)	0.00067 (17)	0.00183 (16)	−0.00052 (15)

C1—C6	1.387 (3)	C8—C9	1.537 (3)
C1—C2	1.405 (2)	C9—H9A	0.9600
C1—S1	1.7570 (17)	C9—H9B	0.9600
C2—C3	1.391 (3)	C9—H9C	0.9600
C2—C12	1.506 (3)	C10—H10A	0.9600
C3—C4	1.375 (3)	C10—H10B	0.9600
C3—H3	0.9300	C10—H10C	0.9600
C4—C5	1.374 (3)	C11—H11A	0.9600
C4—H4	0.9300	C11—H11B	0.9600
C5—C6	1.376 (3)	C11—H11C	0.9600
C5—H5	0.9300	C12—H12A	0.9600
C6—H6	0.9300	C12—H12B	0.9600
C7—O3	1.203 (2)	C12—H12C	0.9600
C7—N1	1.393 (2)	N1—S1	1.6459 (14)
C7—C8	1.526 (2)	N1—H1N	0.817 (16)
C8—C10	1.511 (4)	O1—S1	1.4330 (13)
C8—C11	1.520 (3)	O2—S1	1.4204 (13)
C6—C1—C2	121.63 (17)	C8—C9—H9C	109.5
C6—C1—S1	116.41 (14)	H9A—C9—H9C	109.5
C2—C1—S1	121.78 (14)	H9B—C9—H9C	109.5
C3—C2—C1	116.41 (18)	C8—C10—H10A	109.5
C3—C2—C12	119.35 (18)	C8—C10—H10B	109.5
C1—C2—C12	124.24 (18)	H10A—C10—H10B	109.5
C4—C3—C2	122.0 (2)	C8—C10—H10C	109.5
C4—C3—H3	119.0	H10A—C10—H10C	109.5
C2—C3—H3	119.0	H10B—C10—H10C	109.5
C5—C4—C3	120.4 (2)	C8—C11—H11A	109.5
C5—C4—H4	119.8	C8—C11—H11B	109.5
C3—C4—H4	119.8	H11A—C11—H11B	109.5
C4—C5—C6	119.7 (2)	C8—C11—H11C	109.5
C4—C5—H5	120.1	H11A—C11—H11C	109.5
C6—C5—H5	120.1	H11B—C11—H11C	109.5
C5—C6—C1	119.75 (19)	C2—C12—H12A	109.5
C5—C6—H6	120.1	C2—C12—H12B	109.5
C1—C6—H6	120.1	H12A—C12—H12B	109.5
O3—C7—N1	120.29 (16)	C2—C12—H12C	109.5
O3—C7—C8	125.23 (17)	H12A—C12—H12C	109.5
N1—C7—C8	114.48 (16)	H12B—C12—H12C	109.5
C10—C8—C11	112.3 (2)	C7—N1—S1	124.33 (13)
C10—C8—C7	109.58 (19)	C7—N1—H1N	121.7 (15)
C11—C8—C7	108.65 (18)	S1—N1—H1N	113.9 (15)
C10—C8—C9	108.8 (3)	O2—S1—O1	117.84 (8)
C11—C8—C9	108.3 (2)	O2—S1—N1	109.75 (8)
C7—C8—C9	109.25 (17)	O1—S1—N1	103.69 (7)
C8—C9—H9A	109.5	O2—S1—C1	108.90 (8)
C8—C9—H9B	109.5	O1—S1—C1	108.99 (8)
H9A—C9—H9B	109.5	N1—S1—C1	107.11 (8)
C6—C1—C2—C3	1.3 (3)	N1—C7—C8—C11	−176.7 (2)
S1—C1—C2—C3	−173.65 (13)	O3—C7—C8—C9	120.8 (2)
C6—C1—C2—C12	−177.79 (19)	N1—C7—C8—C9	−58.8 (2)
S1—C1—C2—C12	7.3 (3)	O3—C7—N1—S1	1.5 (3)
C1—C2—C3—C4	0.8 (3)	C8—C7—N1—S1	−178.99 (14)
C12—C2—C3—C4	179.9 (2)	C7—N1—S1—O2	52.69 (18)
C2—C3—C4—C5	−1.6 (3)	C7—N1—S1—O1	179.43 (15)
C3—C4—C5—C6	0.3 (3)	C7—N1—S1—C1	−65.39 (17)
C4—C5—C6—C1	1.8 (3)	C6—C1—S1—O2	2.45 (16)
C2—C1—C6—C5	−2.6 (3)	C2—C1—S1—O2	177.61 (13)
S1—C1—C6—C5	172.59 (15)	C6—C1—S1—O1	−127.33 (13)
O3—C7—C8—C10	−120.1 (3)	C2—C1—S1—O1	47.82 (15)
N1—C7—C8—C10	60.3 (3)	C6—C1—S1—N1	121.08 (14)
O3—C7—C8—C11	2.9 (3)	C2—C1—S1—N1	−63.76 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.82 (2)	2.10 (2)	2.906 (2)	170 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.82 (2)	2.10 (2)	2.906 (2)	170 (2)

Symmetry code: (i) .