2,2,2-Trimethyl-N-(4-methyl-phenyl-sulfon-yl)acetamide.

The bond parameters and conformations of the N-H and C=O bonds of the SO(2)-NH-CO-C group in the title compound, C(12)H(17)NO(3)S, anti to each other, are similar to what has been observed in related structures. The benzene ring and the SO(2)-NH-CO-C group make a dihedral angle of 71.2 (1)°. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For related literature, see: Gowda et al. (2003 ▶, 2007 ▶, 2008 ▶).

Experimental

Crystal data

C12H17NO3S

M = 255.34

Triclinic,

a = 6.695 (1) Å

b = 8.953 (2) Å

c = 12.040 (2) Å

α = 80.21 (1)°

β = 78.51 (1)°

γ = 88.98 (1)°

V = 696.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 299 (2) K

0.50 × 0.32 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.894, T max = 0.978

8562 measured reflections

2827 independent reflections

1947 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.142

S = 1.02

2827 reflections

182 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017790/rk2096sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017790/rk2096Isup2.hkl

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

C12H17NO3S	Z = 2
Mr = 255.34	F000 = 272
Triclinic, P1	Dx = 1.217 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.695 (1) Å	Cell parameters from 1734 reflections
b = 8.953 (2) Å	θ = 2.3–28.0º
c = 12.040 (2) Å	µ = 0.23 mm−1
α = 80.21 (1)º	T = 299 (2) K
β = 78.51 (1)º	Plate, colourless
γ = 88.98 (1)º	0.50 × 0.32 × 0.10 mm
V = 696.8 (2) Å3

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2827 independent reflections
Radiation source: Fine–focus sealed tube	1947 reflections with I > 2σ(I)
Monochromator: Graphite	Rint = 0.023
T = 299(2) K	θmax = 26.4º
ω and φ scans	θmin = 2.3º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −8→8
Tmin = 0.894, Tmax = 0.978	k = −11→11
8562 measured reflections	l = −14→15

Refinement on F2	Secondary atom site location: Difmap
Least-squares matrix: Full	Hydrogen site location: Geom
R[F2 > 2σ(F2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0808P)2 + 0.1297P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.038
2827 reflections	Δρmax = 0.33 e Å−3
182 parameters	Δρmin = −0.34 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: Direct

Experimental. CrysAlis RED, Oxford Diffraction Ltd., 2007 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
C1	0.1874 (3)	0.8846 (2)	0.75440 (18)	0.0516 (5)
C2	0.3230 (3)	0.8778 (3)	0.65199 (19)	0.0594 (6)
H2	0.4609	0.8988	0.6453	0.071*
C3	0.2531 (4)	0.8401 (3)	0.5608 (2)	0.0683 (6)
H3	0.3445	0.8360	0.4923	0.082*
C4	0.0483 (4)	0.8079 (3)	0.5687 (2)	0.0709 (7)
C5	−0.0839 (4)	0.8185 (3)	0.6716 (3)	0.0791 (8)
H5	−0.2221	0.7987	0.6783	0.095*
C6	−0.0172 (3)	0.8569 (3)	0.7630 (2)	0.0678 (6)
H6	−0.1093	0.8643	0.8307	0.081*
C7	0.3855 (4)	1.2106 (3)	0.7911 (2)	0.0639 (6)
C8	0.3541 (4)	1.3752 (3)	0.8054 (2)	0.0701 (7)
C9A	0.1437 (11)	1.4233 (10)	0.7939 (9)	0.100 (3)	0.50
H9A	0.0464	1.3618	0.8524	0.120*	0.50
H9B	0.1219	1.4113	0.7195	0.120*	0.50
H9C	0.1274	1.5278	0.8025	0.120*	0.50
C10A	0.5538 (16)	1.4617 (14)	0.7800 (13)	0.177 (7)	0.50
H10A	0.6243	1.4556	0.7033	0.213*	0.50
H10B	0.6360	1.4187	0.8338	0.213*	0.50
H10C	0.5281	1.5660	0.7867	0.213*	0.50
C11A	0.3989 (18)	1.3949 (12)	0.9168 (9)	0.196 (10)	0.50
H11A	0.5374	1.3672	0.9193	0.235*	0.50
H11B	0.3084	1.3313	0.9777	0.235*	0.50
H11C	0.3802	1.4989	0.9262	0.235*	0.50
C9B	0.1959 (18)	1.4340 (12)	0.7407 (9)	0.261 (14)	0.50
H9D	0.0703	1.3790	0.7733	0.314*	0.50
H9E	0.2375	1.4234	0.6615	0.314*	0.50
H9F	0.1766	1.5393	0.7460	0.314*	0.50
C10B	0.4889 (17)	1.4674 (8)	0.6990 (9)	0.127 (4)	0.50
H10D	0.4484	1.4464	0.6310	0.152*	0.50
H10E	0.6287	1.4400	0.6971	0.152*	0.50
H10F	0.4742	1.5735	0.7022	0.152*	0.50
C11B	0.2711 (16)	1.3977 (11)	0.9308 (7)	0.099 (3)	0.50
H11D	0.3680	1.3606	0.9775	0.119*	0.50
H11E	0.1444	1.3427	0.9599	0.119*	0.50
H11F	0.2494	1.5035	0.9328	0.119*	0.50
C12	−0.0265 (5)	0.7606 (4)	0.4700 (3)	0.1004 (10)
H12A	−0.0457	0.6525	0.4840	0.120*
H12B	0.0722	0.7904	0.4002	0.120*
H12C	−0.1536	0.8087	0.4627	0.120*
N1	0.2641 (3)	1.1039 (2)	0.87314 (17)	0.0608 (5)
H1N	0.171 (4)	1.125 (3)	0.919 (2)	0.073*
O1	0.1327 (3)	0.85718 (17)	0.97613 (13)	0.0685 (5)
O2	0.4839 (2)	0.87466 (19)	0.86454 (14)	0.0702 (5)
O3	0.5046 (3)	1.1703 (2)	0.71397 (17)	0.0929 (6)
S1	0.27716 (8)	0.91984 (6)	0.87499 (4)	0.0559 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0458 (11)	0.0419 (10)	0.0596 (12)	0.0075 (8)	0.0015 (9)	−0.0024 (9)
C2	0.0520 (12)	0.0601 (13)	0.0604 (13)	0.0020 (10)	0.0012 (10)	−0.0089 (10)
C3	0.0722 (16)	0.0665 (15)	0.0615 (14)	0.0057 (12)	−0.0020 (12)	−0.0114 (11)
C4	0.0814 (17)	0.0575 (14)	0.0755 (16)	0.0051 (12)	−0.0248 (14)	−0.0057 (12)
C5	0.0550 (14)	0.0894 (19)	0.0890 (19)	0.0024 (13)	−0.0138 (14)	−0.0047 (15)
C6	0.0512 (13)	0.0781 (16)	0.0664 (15)	0.0075 (11)	0.0001 (11)	−0.0052 (12)
C7	0.0625 (14)	0.0571 (13)	0.0663 (14)	−0.0074 (11)	−0.0023 (12)	−0.0058 (11)
C8	0.0807 (17)	0.0509 (13)	0.0763 (16)	−0.0078 (12)	−0.0163 (13)	−0.0027 (11)
C9A	0.086 (4)	0.065 (4)	0.154 (8)	0.005 (3)	−0.031 (5)	−0.022 (4)
C10A	0.134 (8)	0.151 (9)	0.228 (14)	−0.094 (7)	0.083 (9)	−0.110 (10)
C11A	0.37 (3)	0.084 (6)	0.205 (15)	0.025 (12)	−0.223 (19)	−0.044 (8)
C9B	0.51 (3)	0.132 (10)	0.268 (18)	0.156 (15)	−0.32 (2)	−0.113 (11)
C10B	0.138 (8)	0.044 (3)	0.164 (9)	−0.010 (4)	0.031 (7)	0.006 (4)
C11B	0.152 (8)	0.055 (4)	0.091 (5)	−0.010 (4)	−0.010 (5)	−0.023 (4)
C12	0.124 (3)	0.088 (2)	0.099 (2)	0.0007 (19)	−0.048 (2)	−0.0169 (17)
N1	0.0642 (12)	0.0479 (10)	0.0605 (11)	0.0012 (8)	0.0108 (9)	−0.0086 (8)
O1	0.0794 (11)	0.0538 (9)	0.0583 (9)	0.0055 (8)	0.0097 (8)	0.0015 (7)
O2	0.0580 (10)	0.0762 (11)	0.0751 (11)	0.0184 (8)	−0.0113 (8)	−0.0134 (8)
O3	0.0956 (14)	0.0753 (12)	0.0865 (13)	−0.0155 (10)	0.0340 (11)	−0.0132 (10)
S1	0.0568 (4)	0.0479 (3)	0.0556 (3)	0.0077 (2)	0.0021 (2)	−0.0040 (2)

C1—C6	1.377 (3)	C9A—H9C	0.9600
C1—C2	1.388 (3)	C10A—H10A	0.9600
C1—S1	1.755 (2)	C10A—H10B	0.9600
C2—C3	1.370 (3)	C10A—H10C	0.9600
C2—H2	0.9300	C11A—H11A	0.9600
C3—C4	1.387 (4)	C11A—H11B	0.9600
C3—H3	0.9300	C11A—H11C	0.9600
C4—C5	1.388 (4)	C9B—H9D	0.9600
C4—C12	1.503 (4)	C9B—H9E	0.9600
C5—C6	1.363 (4)	C9B—H9F	0.9600
C5—H5	0.9300	C10B—H10D	0.9600
C6—H6	0.9300	C10B—H10E	0.9600
C7—O3	1.199 (3)	C10B—H10F	0.9600
C7—N1	1.391 (3)	C11B—H11D	0.9600
C7—C8	1.519 (3)	C11B—H11E	0.9600
C8—C9B	1.474 (8)	C11B—H11F	0.9600
C8—C11A	1.471 (8)	C12—H12A	0.9600
C8—C9A	1.492 (7)	C12—H12B	0.9600
C8—C10A	1.508 (8)	C12—H12C	0.9600
C8—C10B	1.530 (7)	N1—S1	1.645 (2)
C8—C11B	1.548 (8)	N1—H1N	0.79 (3)
C9A—H9A	0.9600	O1—S1	1.4322 (15)
C9A—H9B	0.9600	O2—S1	1.4226 (16)
C6—C1—C2	119.9 (2)	H9C—C9A—H9D	124.4
C6—C1—S1	119.81 (17)	C8—C9A—H9F	99.8
C2—C1—S1	120.19 (17)	H9A—C9A—H9F	143.6
C3—C2—C1	119.7 (2)	H9B—C9A—H9F	79.1
C3—C2—H2	120.1	H9C—C9A—H9F	38.1
C1—C2—H2	120.1	H9D—C9A—H9F	115.2
C2—C3—C4	121.2 (2)	C8—C10A—H10A	109.5
C2—C3—H3	119.4	C8—C10A—H10B	109.5
C4—C3—H3	119.4	H10A—C10A—H10B	109.5
C3—C4—C5	117.6 (2)	C8—C10A—H10C	109.5
C3—C4—C12	121.0 (3)	H10A—C10A—H10C	109.5
C5—C4—C12	121.3 (3)	H10B—C10A—H10C	109.5
C6—C5—C4	122.0 (2)	C8—C11A—H11A	109.5
C6—C5—H5	119.0	C8—C11A—H11B	109.5
C4—C5—H5	119.0	H11A—C11A—H11B	109.5
C5—C6—C1	119.5 (2)	C8—C11A—H11C	109.5
C5—C6—H6	120.3	H11A—C11A—H11C	109.5
C1—C6—H6	120.3	H11B—C11A—H11C	109.5
O3—C7—N1	119.9 (2)	C8—C9B—H9D	109.6
O3—C7—C8	123.8 (2)	C8—C9B—H9E	110.1
N1—C7—C8	116.3 (2)	H9D—C9B—H9E	109.5
C9B—C8—C11A	133.9 (8)	C8—C9B—H9F	108.6
C9B—C8—C9A	25.6 (7)	H9D—C9B—H9F	109.5
C11A—C8—C9A	112.1 (6)	H9E—C9B—H9F	109.5
C9B—C8—C10A	118.0 (9)	C8—C10B—H10D	109.5
C11A—C8—C10A	73.2 (8)	C8—C10B—H10E	109.5
C9A—C8—C10A	132.1 (7)	H10D—C10B—H10E	109.5
C9B—C8—C7	106.9 (4)	C8—C10B—H10F	109.5
C11A—C8—C7	109.0 (4)	H10D—C10B—H10F	109.5
C9A—C8—C7	110.8 (4)	H10E—C10B—H10F	109.5
C10A—C8—C7	111.7 (5)	C8—C11B—H11D	109.5
C9B—C8—C10B	80.5 (7)	C8—C11B—H11E	109.5
C11A—C8—C10B	115.8 (8)	H11D—C11B—H11E	109.5
C9A—C8—C10B	103.5 (6)	C8—C11B—H11F	109.5
C10A—C8—C10B	44.0 (6)	H11D—C11B—H11F	109.5
C7—C8—C10B	105.3 (4)	H11E—C11B—H11F	109.5
C9B—C8—C11B	105.6 (7)	C4—C12—H12A	109.5
C11A—C8—C11B	32.2 (6)	C4—C12—H12B	109.5
C9A—C8—C11B	81.3 (6)	H12A—C12—H12B	109.5
C10A—C8—C11B	100.5 (6)	C4—C12—H12C	109.5
C7—C8—C11B	114.1 (4)	H12A—C12—H12C	109.5
C10B—C8—C11B	135.7 (5)	H12B—C12—H12C	109.5
C8—C9A—H9A	109.5	C7—N1—S1	124.02 (17)
C8—C9A—H9B	109.5	C7—N1—H1N	124.0 (19)
H9A—C9A—H9B	109.5	S1—N1—H1N	111.5 (19)
C8—C9A—H9C	109.5	O2—S1—O1	118.88 (10)
H9A—C9A—H9C	109.5	O2—S1—N1	109.50 (10)
H9B—C9A—H9C	109.5	O1—S1—N1	103.95 (9)
C8—C9A—H9D	125.1	O2—S1—C1	108.79 (10)
H9A—C9A—H9D	64.0	O1—S1—C1	108.34 (10)
H9B—C9A—H9D	45.5	N1—S1—C1	106.71 (10)
C6—C1—C2—C3	−1.5 (3)	N1—C7—C8—C10A	139.4 (7)
S1—C1—C2—C3	175.60 (17)	O3—C7—C8—C10B	4.5 (6)
C1—C2—C3—C4	−0.2 (4)	N1—C7—C8—C10B	−174.6 (5)
C2—C3—C4—C5	1.3 (4)	O3—C7—C8—C11B	−154.7 (5)
C2—C3—C4—C12	−177.6 (2)	N1—C7—C8—C11B	26.3 (5)
C3—C4—C5—C6	−0.9 (4)	O3—C7—N1—S1	2.2 (4)
C12—C4—C5—C6	178.0 (2)	C8—C7—N1—S1	−178.70 (17)
C4—C5—C6—C1	−0.8 (4)	C7—N1—S1—O2	49.4 (2)
C2—C1—C6—C5	2.0 (3)	C7—N1—S1—O1	177.46 (19)
S1—C1—C6—C5	−175.16 (18)	C7—N1—S1—C1	−68.1 (2)
O3—C7—C8—C9B	88.9 (6)	C6—C1—S1—O2	152.78 (18)
N1—C7—C8—C9B	−90.1 (6)	C2—C1—S1—O2	−24.3 (2)
O3—C7—C8—C11A	−120.5 (6)	C6—C1—S1—O1	22.2 (2)
N1—C7—C8—C11A	60.5 (6)	C2—C1—S1—O1	−154.90 (17)
O3—C7—C8—C9A	115.7 (5)	C6—C1—S1—N1	−89.16 (19)
N1—C7—C8—C9A	−63.3 (5)	C2—C1—S1—N1	93.72 (18)
O3—C7—C8—C10A	−41.6 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.79 (3)	2.19 (3)	2.955 (2)	164 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.79 (3)	2.19 (3)	2.955 (2)	164 (3)

Symmetry code: (i) .