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

The N-H and C=O bonds of the SO(2)-NH-CO group in the title compound, C(11)H(15)NO(3)S, are anti to each other. The asymmetric unit contains two independent mol-ecules. The benzene rings form dihedral angles of 83.19 (8) and 76.01 (10)° with the mean planes of the C(2)NOS fragments. The mol-ecules are linked into chains parallel to the b axis by inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related literature, see: Gowda, Nayak et al. (2007 ▶); Gowda, Foro & Fuess (2007 ▶); Gowda, Kožíšek et al. (2007 ▶); Gowda, Svoboda et al. (2007 ▶).

Experimental

Crystal data

C11H15NO3S

M = 241.30

Monoclinic,

a = 12.3045 (9) Å

b = 11.3016 (7) Å

c = 18.466 (1) Å

β = 103.117 (6)°

V = 2500.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 299 (2) K

0.50 × 0.48 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.885, T max = 0.906

15589 measured reflections

4985 independent reflections

3639 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.167

S = 1.16

4985 reflections

290 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.40 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/S1600536808019983/rz2222sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019983/rz2222Isup2.hkl

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

C11H15NO3S	F000 = 1024
Mr = 241.30	Dx = 1.282 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7426 reflections
a = 12.3045 (9) Å	θ = 2.5–28.0º
b = 11.3016 (7) Å	µ = 0.25 mm−1
c = 18.466 (1) Å	T = 299 (2) K
β = 103.117 (6)º	Prism, colourless
V = 2500.9 (3) Å3	0.50 × 0.48 × 0.40 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4985 independent reflections
Radiation source: fine-focus sealed tube	3639 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
T = 299(2) K	θmax = 26.4º
Rotation method data acquisition using ω and φ scans	θmin = 2.5º
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	h = −15→15
Tmin = 0.885, Tmax = 0.906	k = −13→13
15589 measured reflections	l = −21→22

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051	w = 1/[σ2(Fo2) + (0.0676P)2 + 1.8991P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.167	(Δ/σ)max = 0.002
S = 1.16	Δρmax = 0.44 e Å−3
4985 reflections	Δρmin = −0.40 e Å−3
290 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.100 (4)
Secondary atom site location: difference Fourier map

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	0.6562 (2)	0.7079 (2)	0.00179 (14)	0.0448 (6)
C2	0.7702 (3)	0.7222 (3)	0.00846 (18)	0.0580 (8)
H2	0.8043	0.7948	0.0223	0.070*
C3	0.8318 (3)	0.6267 (3)	−0.0058 (2)	0.0693 (9)
H3	0.9082	0.6350	−0.0015	0.083*
C4	0.7817 (3)	0.5195 (3)	−0.02624 (19)	0.0679 (9)
H4	0.8244	0.4554	−0.0350	0.081*
C5	0.6688 (3)	0.5067 (3)	−0.03380 (18)	0.0624 (8)
H5	0.6350	0.4344	−0.0486	0.075*
C6	0.6053 (3)	0.6003 (3)	−0.01956 (16)	0.0515 (7)
H6	0.5289	0.5913	−0.0242	0.062*
C7	0.5886 (2)	0.7797 (2)	0.15920 (15)	0.0440 (6)
C8	0.6204 (3)	0.8245 (3)	0.23927 (15)	0.0541 (7)
C9	0.5795 (4)	0.7357 (4)	0.2886 (2)	0.0894 (13)
H9A	0.6138	0.6603	0.2849	0.107*
H9B	0.5000	0.7281	0.2730	0.107*
H9C	0.5990	0.7625	0.3393	0.107*
C10	0.5687 (3)	0.9456 (3)	0.24601 (19)	0.0713 (9)
H10A	0.4889	0.9399	0.2307	0.086*
H10B	0.5953	1.0013	0.2148	0.086*
H10C	0.5892	0.9718	0.2967	0.086*
C11	0.7482 (3)	0.8339 (4)	0.2623 (2)	0.0856 (12)
H11A	0.7740	0.8874	0.2295	0.103*
H11B	0.7805	0.7572	0.2596	0.103*
H11C	0.7698	0.8630	0.3124	0.103*
N1	0.6084 (2)	0.8572 (2)	0.10554 (12)	0.0499 (6)
H1N	0.6401	0.9236	0.1200	0.060*
O1	0.46068 (17)	0.79593 (19)	−0.00518 (12)	0.0590 (6)
O2	0.6126 (2)	0.93176 (18)	−0.01691 (11)	0.0613 (6)
O3	0.54943 (18)	0.68328 (17)	0.14170 (11)	0.0541 (5)
S1	0.57470 (6)	0.82976 (6)	0.01579 (4)	0.0467 (2)
C12	0.8299 (2)	0.2840 (2)	0.14176 (14)	0.0476 (6)
C13	0.9320 (3)	0.3399 (3)	0.15839 (18)	0.0678 (9)
H13	0.9972	0.2991	0.1572	0.081*
C14	0.9346 (6)	0.4580 (5)	0.1769 (2)	0.1085 (19)
H14	1.0028	0.4973	0.1888	0.130*
C15	0.8403 (8)	0.5176 (4)	0.1781 (3)	0.120 (2)
H15	0.8442	0.5975	0.1905	0.144*
C16	0.7397 (5)	0.4626 (4)	0.1615 (2)	0.0985 (16)
H16	0.6752	0.5051	0.1625	0.118*
C17	0.7324 (3)	0.3431 (3)	0.14311 (17)	0.0657 (9)
H17	0.6640	0.3042	0.1321	0.079*
C18	0.8663 (2)	0.1631 (3)	−0.01406 (16)	0.0531 (7)
C19	0.8292 (3)	0.1401 (3)	−0.09727 (16)	0.0547 (7)
C20	0.9144 (4)	0.1923 (4)	−0.1351 (2)	0.0894 (13)
H20A	0.9856	0.1557	−0.1160	0.107*
H20B	0.9202	0.2759	−0.1258	0.107*
H20C	0.8918	0.1785	−0.1877	0.107*
C21	0.8234 (4)	0.0072 (4)	−0.1109 (2)	0.0822 (11)
H21A	0.7707	−0.0273	−0.0859	0.099*
H21B	0.8957	−0.0271	−0.0921	0.099*
H21C	0.8002	−0.0079	−0.1633	0.099*
C22	0.7149 (4)	0.1925 (5)	−0.1277 (2)	0.0991 (15)
H22A	0.7175	0.2764	−0.1193	0.119*
H22B	0.6622	0.1573	−0.1030	0.119*
H22C	0.6925	0.1771	−0.1801	0.119*
N2	0.7948 (2)	0.1235 (2)	0.02886 (12)	0.0541 (6)
H2N	0.7323	0.0925	0.0067	0.065*
O4	0.7261 (2)	0.0845 (2)	0.13953 (12)	0.0719 (7)
O5	0.9285 (2)	0.0813 (2)	0.15009 (14)	0.0811 (8)
O6	0.9519 (2)	0.2109 (3)	0.01479 (13)	0.0823 (8)
S2	0.82357 (6)	0.13285 (7)	0.12026 (4)	0.0512 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0553 (15)	0.0441 (14)	0.0354 (12)	−0.0074 (12)	0.0111 (11)	−0.0005 (10)
C2	0.0561 (17)	0.0525 (17)	0.0625 (18)	−0.0116 (14)	0.0070 (14)	0.0000 (14)
C3	0.0572 (19)	0.076 (2)	0.077 (2)	0.0004 (17)	0.0198 (16)	0.0044 (18)
C4	0.081 (2)	0.061 (2)	0.068 (2)	0.0118 (17)	0.0315 (17)	−0.0010 (16)
C5	0.082 (2)	0.0481 (17)	0.0640 (19)	−0.0070 (15)	0.0306 (16)	−0.0093 (14)
C6	0.0598 (17)	0.0494 (16)	0.0481 (15)	−0.0122 (13)	0.0184 (12)	−0.0038 (12)
C7	0.0478 (14)	0.0402 (14)	0.0453 (14)	0.0023 (11)	0.0132 (11)	−0.0035 (11)
C8	0.0719 (19)	0.0524 (16)	0.0370 (14)	−0.0026 (14)	0.0103 (13)	−0.0038 (12)
C9	0.144 (4)	0.079 (3)	0.0471 (18)	−0.019 (3)	0.027 (2)	0.0023 (17)
C10	0.092 (3)	0.067 (2)	0.0593 (19)	0.0040 (19)	0.0272 (18)	−0.0160 (16)
C11	0.082 (3)	0.099 (3)	0.064 (2)	0.008 (2)	−0.0068 (19)	−0.011 (2)
N1	0.0684 (15)	0.0436 (12)	0.0376 (11)	−0.0118 (11)	0.0119 (10)	−0.0049 (9)
O1	0.0524 (12)	0.0616 (13)	0.0582 (12)	0.0000 (10)	0.0025 (9)	−0.0063 (10)
O2	0.0892 (16)	0.0466 (11)	0.0499 (11)	−0.0053 (11)	0.0195 (10)	0.0045 (9)
O3	0.0697 (13)	0.0420 (11)	0.0520 (11)	−0.0059 (9)	0.0165 (9)	−0.0025 (8)
S1	0.0585 (4)	0.0419 (4)	0.0387 (4)	−0.0035 (3)	0.0088 (3)	−0.0003 (3)
C12	0.0596 (17)	0.0470 (15)	0.0345 (13)	−0.0036 (12)	0.0071 (11)	−0.0018 (11)
C13	0.077 (2)	0.075 (2)	0.0491 (17)	−0.0233 (18)	0.0108 (15)	−0.0077 (15)
C14	0.172 (5)	0.084 (3)	0.068 (3)	−0.066 (4)	0.023 (3)	−0.021 (2)
C15	0.244 (8)	0.054 (3)	0.064 (3)	−0.014 (4)	0.039 (4)	−0.011 (2)
C16	0.164 (5)	0.078 (3)	0.057 (2)	0.056 (3)	0.031 (3)	0.005 (2)
C17	0.077 (2)	0.072 (2)	0.0467 (16)	0.0168 (17)	0.0098 (15)	0.0002 (15)
C18	0.0506 (16)	0.0640 (18)	0.0474 (16)	−0.0065 (14)	0.0164 (12)	−0.0095 (13)
C19	0.0563 (17)	0.0657 (19)	0.0445 (15)	−0.0009 (14)	0.0164 (12)	−0.0089 (13)
C20	0.111 (3)	0.112 (3)	0.053 (2)	−0.033 (3)	0.036 (2)	−0.012 (2)
C21	0.114 (3)	0.074 (2)	0.068 (2)	−0.010 (2)	0.040 (2)	−0.0204 (18)
C22	0.085 (3)	0.152 (4)	0.056 (2)	0.037 (3)	0.0070 (19)	−0.008 (2)
N2	0.0570 (14)	0.0692 (16)	0.0382 (12)	−0.0159 (12)	0.0152 (10)	−0.0152 (11)
O4	0.0986 (18)	0.0684 (15)	0.0565 (13)	−0.0316 (13)	0.0338 (12)	−0.0093 (11)
O5	0.0916 (18)	0.0805 (17)	0.0672 (15)	0.0328 (14)	0.0099 (13)	0.0079 (13)
O6	0.0625 (14)	0.132 (2)	0.0541 (13)	−0.0361 (15)	0.0165 (11)	−0.0164 (14)
S2	0.0652 (5)	0.0477 (4)	0.0410 (4)	−0.0019 (3)	0.0130 (3)	−0.0016 (3)

C1—C6	1.384 (4)	C12—C13	1.377 (4)
C1—C2	1.389 (4)	C12—C17	1.378 (4)
C1—S1	1.757 (3)	C12—S2	1.752 (3)
C2—C3	1.378 (5)	C13—C14	1.376 (6)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.373 (5)	C14—C15	1.347 (8)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.372 (5)	C15—C16	1.357 (8)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.375 (4)	C16—C17	1.391 (6)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—O3	1.206 (3)	C18—O6	1.195 (4)
C7—N1	1.384 (3)	C18—N2	1.386 (4)
C7—C8	1.527 (4)	C18—C19	1.523 (4)
C8—C9	1.516 (5)	C19—C20	1.506 (5)
C8—C10	1.526 (5)	C19—C22	1.512 (5)
C8—C11	1.536 (5)	C19—C21	1.522 (5)
C9—H9A	0.9600	C20—H20A	0.9600
C9—H9B	0.9600	C20—H20B	0.9600
C9—H9C	0.9600	C20—H20C	0.9600
C10—H10A	0.9600	C21—H21A	0.9600
C10—H10B	0.9600	C21—H21B	0.9600
C10—H10C	0.9600	C21—H21C	0.9600
C11—H11A	0.9600	C22—H22A	0.9600
C11—H11B	0.9600	C22—H22B	0.9600
C11—H11C	0.9600	C22—H22C	0.9600
N1—S1	1.644 (2)	N2—S2	1.647 (2)
N1—H1N	0.8600	N2—H2N	0.8600
O1—S1	1.421 (2)	O4—S2	1.434 (2)
O2—S1	1.428 (2)	O5—S2	1.410 (2)
C6—C1—C2	120.7 (3)	C13—C12—C17	121.9 (3)
C6—C1—S1	119.6 (2)	C13—C12—S2	119.3 (3)
C2—C1—S1	119.6 (2)	C17—C12—S2	118.8 (2)
C3—C2—C1	118.7 (3)	C14—C13—C12	118.0 (4)
C3—C2—H2	120.7	C14—C13—H13	121.0
C1—C2—H2	120.7	C12—C13—H13	121.0
C4—C3—C2	120.8 (3)	C15—C14—C13	121.2 (5)
C4—C3—H3	119.6	C15—C14—H14	119.4
C2—C3—H3	119.6	C13—C14—H14	119.4
C5—C4—C3	120.1 (3)	C14—C15—C16	120.9 (4)
C5—C4—H4	119.9	C14—C15—H15	119.6
C3—C4—H4	119.9	C16—C15—H15	119.6
C4—C5—C6	120.4 (3)	C15—C16—C17	120.3 (5)
C4—C5—H5	119.8	C15—C16—H16	119.9
C6—C5—H5	119.8	C17—C16—H16	119.9
C5—C6—C1	119.4 (3)	C12—C17—C16	117.8 (4)
C5—C6—H6	120.3	C12—C17—H17	121.1
C1—C6—H6	120.3	C16—C17—H17	121.1
O3—C7—N1	120.3 (2)	O6—C18—N2	120.0 (3)
O3—C7—C8	123.9 (3)	O6—C18—C19	124.0 (3)
N1—C7—C8	115.8 (2)	N2—C18—C19	116.0 (2)
C9—C8—C10	110.1 (3)	C20—C19—C22	111.2 (4)
C9—C8—C7	108.4 (3)	C20—C19—C21	108.7 (3)
C10—C8—C7	110.9 (2)	C22—C19—C21	108.7 (3)
C9—C8—C11	109.7 (3)	C20—C19—C18	108.7 (3)
C10—C8—C11	109.6 (3)	C22—C19—C18	110.4 (3)
C7—C8—C11	108.2 (3)	C21—C19—C18	109.1 (3)
C8—C9—H9A	109.5	C19—C20—H20A	109.5
C8—C9—H9B	109.5	C19—C20—H20B	109.5
H9A—C9—H9B	109.5	H20A—C20—H20B	109.5
C8—C9—H9C	109.5	C19—C20—H20C	109.5
H9A—C9—H9C	109.5	H20A—C20—H20C	109.5
H9B—C9—H9C	109.5	H20B—C20—H20C	109.5
C8—C10—H10A	109.5	C19—C21—H21A	109.5
C8—C10—H10B	109.5	C19—C21—H21B	109.5
H10A—C10—H10B	109.5	H21A—C21—H21B	109.5
C8—C10—H10C	109.5	C19—C21—H21C	109.5
H10A—C10—H10C	109.5	H21A—C21—H21C	109.5
H10B—C10—H10C	109.5	H21B—C21—H21C	109.5
C8—C11—H11A	109.5	C19—C22—H22A	109.5
C8—C11—H11B	109.5	C19—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
C8—C11—H11C	109.5	C19—C22—H22C	109.5
H11A—C11—H11C	109.5	H22A—C22—H22C	109.5
H11B—C11—H11C	109.5	H22B—C22—H22C	109.5
C7—N1—S1	123.86 (19)	C18—N2—S2	123.3 (2)
C7—N1—H1N	118.1	C18—N2—H2N	118.4
S1—N1—H1N	118.1	S2—N2—H2N	118.4
O1—S1—O2	119.96 (14)	O5—S2—O4	119.27 (17)
O1—S1—N1	109.45 (13)	O5—S2—N2	109.80 (14)
O2—S1—N1	104.02 (12)	O4—S2—N2	103.43 (13)
O1—S1—C1	108.08 (13)	O5—S2—C12	108.93 (16)
O2—S1—C1	108.55 (13)	O4—S2—C12	108.21 (14)
N1—S1—C1	105.93 (12)	N2—S2—C12	106.43 (13)
C6—C1—C2—C3	−0.7 (4)	C17—C12—C13—C14	0.2 (5)
S1—C1—C2—C3	−177.3 (3)	S2—C12—C13—C14	−178.4 (3)
C1—C2—C3—C4	0.1 (5)	C12—C13—C14—C15	−0.6 (6)
C2—C3—C4—C5	0.9 (5)	C13—C14—C15—C16	0.4 (7)
C3—C4—C5—C6	−1.3 (5)	C14—C15—C16—C17	0.2 (7)
C4—C5—C6—C1	0.6 (5)	C13—C12—C17—C16	0.4 (5)
C2—C1—C6—C5	0.4 (4)	S2—C12—C17—C16	179.0 (3)
S1—C1—C6—C5	177.0 (2)	C15—C16—C17—C12	−0.6 (6)
O3—C7—C8—C9	−7.8 (4)	O6—C18—C19—C20	−2.7 (5)
N1—C7—C8—C9	172.8 (3)	N2—C18—C19—C20	178.1 (3)
O3—C7—C8—C10	−128.7 (3)	O6—C18—C19—C22	−124.9 (4)
N1—C7—C8—C10	51.9 (4)	N2—C18—C19—C22	56.0 (4)
O3—C7—C8—C11	111.1 (3)	O6—C18—C19—C21	115.7 (4)
N1—C7—C8—C11	−68.3 (3)	N2—C18—C19—C21	−63.4 (4)
O3—C7—N1—S1	3.8 (4)	O6—C18—N2—S2	−2.9 (5)
C8—C7—N1—S1	−176.8 (2)	C19—C18—N2—S2	176.2 (2)
C7—N1—S1—O1	51.8 (3)	C18—N2—S2—O5	−53.0 (3)
C7—N1—S1—O2	−178.8 (2)	C18—N2—S2—O4	178.7 (3)
C7—N1—S1—C1	−64.5 (3)	C18—N2—S2—C12	64.7 (3)
C6—C1—S1—O1	−5.4 (3)	C13—C12—S2—O5	22.0 (3)
C2—C1—S1—O1	171.3 (2)	C17—C12—S2—O5	−156.6 (2)
C6—C1—S1—O2	−136.9 (2)	C13—C12—S2—O4	153.0 (2)
C2—C1—S1—O2	39.7 (3)	C17—C12—S2—O4	−25.5 (3)
C6—C1—S1—N1	111.9 (2)	C13—C12—S2—N2	−96.4 (2)
C2—C1—S1—N1	−71.5 (3)	C17—C12—S2—N2	85.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O4i	0.86	2.09	2.946 (3)	171
N2—H2N···O2ii	0.86	2.32	3.094 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O4i	0.86	2.09	2.946 (3)	171
N2—H2N⋯O2ii	0.86	2.32	3.094 (3)	151

Symmetry codes: (i) ; (ii) .