N-(3-Methoxy-phen-yl)-tert-butane-sulfinamide.

In the title compound, C(11)H(17)NO(2)S, the mol-ecules inter-act in a head-to-tail fashion through pairs of N-H⋯O hydrogen bonds, giving discrete centrosymmetric dimers. The N(H)S(O)(t)Bu fragment is disordered over two sets of positions, with the major component comprising 90.0 (2)%.

Related literature

For N-aryl­alkanesulfinamides, see: Datta et al. (2008 ▶, 2009 ▶). For N-alkyl­alkanesulfinamides, see: Sato et al. (1975 ▶); Ferreira et al. (2005 ▶); Schuckmann et al. (1978 ▶). For the synthesis, see: Stretter et al. (1969 ▶).

Experimental

Crystal data

C11H17NO2S

M = 227.32

Monoclinic,

a = 12.4068 (13) Å

b = 7.3076 (8) Å

c = 12.9230 (13) Å

β = 93.2992 (15)°

V = 1169.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 150 K

0.37 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.911, T max = 0.950

10627 measured reflections

2633 independent reflections

2237 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.07

2633 reflections

166 parameters

149 restraints

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052507/ng2698sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052507/ng2698Isup2.hkl

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

C11H17NO2S	F(000) = 488
Mr = 227.32	Dx = 1.291 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4390 reflections
a = 12.4068 (13) Å	θ = 2.2–27.2°
b = 7.3076 (8) Å	µ = 0.26 mm−1
c = 12.9230 (13) Å	T = 150 K
β = 93.2992 (15)°	Block, colourless
V = 1169.7 (2) Å3	0.37 × 0.22 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	2633 independent reflections
Radiation source: fine-focus sealed tube	2237 reflections with I > 2σ(I)
graphite	Rint = 0.032
ω rotation with narrow frames scans	θmax = 27.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −15→16
Tmin = 0.911, Tmax = 0.950	k = −9→9
10627 measured reflections	l = −16→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.056P)2 + 0.7085P] where P = (Fo2 + 2Fc2)/3
2633 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.62 e Å−3
149 restraints	Δρmin = −0.40 e Å−3

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	Occ. (<1)
O1	0.54940 (10)	−0.05258 (18)	0.36978 (10)	0.0229 (3)	0.900 (2)
S1	0.50816 (3)	0.13248 (6)	0.33748 (3)	0.01938 (15)	0.900 (2)
N1	0.42312 (12)	0.2035 (3)	0.42415 (12)	0.0236 (4)	0.900 (2)
H1	0.4482	0.2281	0.4877	0.028*	0.900 (2)
C1	0.31128 (13)	0.2253 (2)	0.39789 (13)	0.0253 (4)
C2	0.24035 (14)	0.2103 (3)	0.47687 (14)	0.0277 (4)
H2	0.2669	0.1811	0.5453	0.033*
C3	0.13034 (14)	0.2383 (3)	0.45550 (14)	0.0289 (4)
O2	0.06872 (11)	0.2258 (3)	0.54029 (11)	0.0462 (4)
C11	−0.04594 (16)	0.2441 (4)	0.52212 (19)	0.0487 (6)
H11A	−0.0626	0.3643	0.4916	0.073*
H11B	−0.0808	0.2325	0.5879	0.073*
H11C	−0.0727	0.1480	0.4744	0.073*
C4	0.08935 (14)	0.2716 (3)	0.35566 (15)	0.0300 (4)
H4	0.0140	0.2867	0.3407	0.036*
C5	0.16122 (16)	0.2821 (3)	0.27816 (15)	0.0384 (5)
H5	0.1340	0.3040	0.2090	0.046*
C6	0.27117 (15)	0.2620 (3)	0.29758 (14)	0.0328 (4)
H6	0.3188	0.2731	0.2429	0.039*
C7	0.62017 (14)	0.2928 (3)	0.36663 (14)	0.0212 (4)	0.900 (2)
C8	0.57870 (17)	0.4793 (3)	0.32914 (18)	0.0314 (5)	0.900 (2)
H8A	0.5209	0.5198	0.3724	0.047*	0.900 (2)
H8B	0.5507	0.4698	0.2569	0.047*	0.900 (2)
H8C	0.6379	0.5682	0.3341	0.047*	0.900 (2)
C9	0.65533 (15)	0.2918 (3)	0.48138 (15)	0.0262 (4)	0.900 (2)
H9A	0.6810	0.1694	0.5015	0.039*	0.900 (2)
H9B	0.5939	0.3248	0.5220	0.039*	0.900 (2)
H9C	0.7137	0.3807	0.4945	0.039*	0.900 (2)
C10	0.7108 (2)	0.2247 (6)	0.3005 (2)	0.0282 (7)	0.900 (2)
H10A	0.7359	0.1048	0.3258	0.042*	0.900 (2)
H10B	0.7710	0.3118	0.3054	0.042*	0.900 (2)
H10C	0.6835	0.2141	0.2281	0.042*	0.900 (2)
O1X	0.5509 (11)	0.5520 (16)	0.3695 (10)	0.032 (3)*	0.100 (2)
S1X	0.5084 (4)	0.3681 (6)	0.3374 (3)	0.0303 (15)*	0.100 (2)
N1X	0.4214 (12)	0.288 (2)	0.4216 (13)	0.026 (4)*	0.100 (2)
H1X	0.4450	0.2833	0.4871	0.032*	0.100 (2)
C7X	0.6173 (12)	0.204 (2)	0.3663 (12)	0.029 (4)*	0.100 (2)
C8X	0.5762 (16)	0.016 (2)	0.3308 (16)	0.034 (4)*	0.100 (2)
H8D	0.5135	−0.0179	0.3694	0.052*	0.100 (2)
H8E	0.6335	−0.0751	0.3436	0.052*	0.100 (2)
H8F	0.5553	0.0197	0.2565	0.052*	0.100 (2)
C9X	0.6514 (16)	0.199 (3)	0.4840 (12)	0.032 (5)*	0.100 (2)
H9D	0.6766	0.3204	0.5065	0.048*	0.100 (2)
H9E	0.7096	0.1097	0.4964	0.048*	0.100 (2)
H9F	0.5893	0.1635	0.5231	0.048*	0.100 (2)
C10X	0.7138 (19)	0.269 (4)	0.308 (2)	0.025 (8)*	0.100 (2)
H10D	0.7374	0.3893	0.3344	0.038*	0.100 (2)
H10E	0.6927	0.2793	0.2338	0.038*	0.100 (2)
H10F	0.7731	0.1813	0.3179	0.038*	0.100 (2)

	U11	U22	U33	U12	U13	U23
O1	0.0234 (6)	0.0218 (7)	0.0233 (6)	0.0001 (5)	0.0005 (5)	0.0005 (5)
S1	0.0152 (2)	0.0251 (2)	0.0179 (2)	0.00068 (16)	0.00179 (14)	0.00043 (17)
N1	0.0151 (8)	0.0366 (11)	0.0193 (8)	0.0024 (7)	0.0019 (6)	0.0015 (7)
C1	0.0168 (8)	0.0337 (10)	0.0254 (9)	0.0007 (6)	0.0014 (6)	0.0012 (7)
C2	0.0215 (9)	0.0385 (10)	0.0230 (8)	−0.0003 (7)	0.0009 (6)	0.0003 (7)
C3	0.0189 (8)	0.0400 (10)	0.0282 (9)	0.0001 (7)	0.0047 (7)	−0.0026 (7)
O2	0.0164 (7)	0.0900 (13)	0.0327 (8)	0.0034 (7)	0.0060 (5)	0.0010 (7)
C11	0.0156 (9)	0.0850 (19)	0.0464 (12)	0.0009 (10)	0.0083 (8)	−0.0025 (12)
C4	0.0180 (8)	0.0380 (10)	0.0336 (10)	0.0047 (7)	−0.0021 (7)	−0.0017 (8)
C5	0.0284 (10)	0.0603 (14)	0.0259 (9)	0.0128 (9)	−0.0022 (7)	0.0034 (9)
C6	0.0243 (9)	0.0504 (12)	0.0241 (9)	0.0076 (8)	0.0050 (7)	0.0068 (8)
C7	0.0165 (8)	0.0226 (10)	0.0251 (9)	−0.0010 (7)	0.0064 (6)	−0.0021 (8)
C8	0.0282 (10)	0.0240 (10)	0.0431 (12)	0.0031 (8)	0.0109 (9)	0.0028 (9)
C9	0.0187 (9)	0.0324 (12)	0.0277 (10)	−0.0042 (8)	0.0026 (7)	−0.0061 (8)
C10	0.0195 (12)	0.0340 (18)	0.0321 (14)	0.0012 (10)	0.0109 (8)	−0.0028 (13)

O1—S1	1.4967 (14)	C8—H8B	0.9800
S1—N1	1.6652 (16)	C8—H8C	0.9800
S1—C7	1.8401 (19)	C9—H9A	0.9800
N1—C1	1.418 (2)	C9—H9B	0.9800
N1—H1	0.8800	C9—H9C	0.9800
C1—C6	1.388 (3)	C10—H10A	0.9800
C1—C2	1.390 (2)	C10—H10B	0.9800
C1—N1X	1.457 (16)	C10—H10C	0.9800
C2—C3	1.392 (2)	O1X—S1X	1.493 (12)
C2—H2	0.9500	S1X—N1X	1.681 (13)
C3—O2	1.375 (2)	S1X—C7X	1.828 (13)
C3—C4	1.381 (3)	N1X—H1X	0.8800
O2—C11	1.435 (2)	C7X—C8X	1.528 (16)
C11—H11A	0.9800	C7X—C10X	1.528 (16)
C11—H11B	0.9800	C7X—C9X	1.555 (15)
C11—H11C	0.9800	C8X—H8D	0.9800
C4—C5	1.381 (3)	C8X—H8E	0.9800
C4—H4	0.9500	C8X—H8F	0.9800
C5—C6	1.381 (3)	C9X—H9D	0.9800
C5—H5	0.9500	C9X—H9E	0.9800
C6—H6	0.9500	C9X—H9F	0.9800
C7—C9	1.522 (3)	C10X—H10D	0.9800
C7—C8	1.526 (3)	C10X—H10E	0.9800
C7—C10	1.534 (3)	C10X—H10F	0.9800
C8—H8A	0.9800
O1—S1—N1	108.28 (9)	H8B—C8—H8C	109.5
O1—S1—C7	106.04 (8)	C7—C9—H9A	109.5
N1—S1—C7	99.44 (9)	C7—C9—H9B	109.5
C1—N1—S1	121.54 (13)	H9A—C9—H9B	109.5
C1—N1—H1	119.2	C7—C9—H9C	109.5
S1—N1—H1	119.2	H9A—C9—H9C	109.5
C6—C1—C2	119.54 (16)	H9B—C9—H9C	109.5
C6—C1—N1	122.58 (16)	C7—C10—H10A	109.5
C2—C1—N1	117.88 (15)	C7—C10—H10B	109.5
C6—C1—N1X	114.7 (6)	H10A—C10—H10B	109.5
C2—C1—N1X	119.7 (6)	C7—C10—H10C	109.5
C1—C2—C3	119.86 (16)	H10A—C10—H10C	109.5
C1—C2—H2	120.1	H10B—C10—H10C	109.5
C3—C2—H2	120.1	O1X—S1X—N1X	111.3 (8)
O2—C3—C4	124.38 (16)	O1X—S1X—C7X	106.8 (8)
O2—C3—C2	114.58 (16)	N1X—S1X—C7X	97.7 (8)
C4—C3—C2	121.03 (17)	C1—N1X—S1X	127.0 (11)
C3—O2—C11	117.06 (16)	C1—N1X—H1X	116.5
O2—C11—H11A	109.5	S1X—N1X—H1X	116.5
O2—C11—H11B	109.5	C8X—C7X—C10X	112.9 (15)
H11A—C11—H11B	109.5	C8X—C7X—C9X	109.8 (14)
O2—C11—H11C	109.5	C10X—C7X—C9X	108.3 (16)
H11A—C11—H11C	109.5	C8X—C7X—S1X	107.4 (11)
H11B—C11—H11C	109.5	C10X—C7X—S1X	106.6 (14)
C5—C4—C3	117.97 (16)	C9X—C7X—S1X	111.8 (11)
C5—C4—H4	121.0	C7X—C8X—H8D	109.5
C3—C4—H4	121.0	C7X—C8X—H8E	109.5
C6—C5—C4	122.33 (17)	H8D—C8X—H8E	109.5
C6—C5—H5	118.8	C7X—C8X—H8F	109.5
C4—C5—H5	118.8	H8D—C8X—H8F	109.5
C5—C6—C1	119.20 (17)	H8E—C8X—H8F	109.5
C5—C6—H6	120.4	C7X—C9X—H9D	109.5
C1—C6—H6	120.4	C7X—C9X—H9E	109.5
C9—C7—C8	112.73 (17)	H9D—C9X—H9E	109.5
C9—C7—C10	111.27 (18)	C7X—C9X—H9F	109.5
C8—C7—C10	110.95 (19)	H9D—C9X—H9F	109.5
C9—C7—S1	111.54 (13)	H9E—C9X—H9F	109.5
C8—C7—S1	105.49 (13)	C7X—C10X—H10D	109.5
C10—C7—S1	104.40 (18)	C7X—C10X—H10E	109.5
C7—C8—H8A	109.5	H10D—C10X—H10E	109.5
C7—C8—H8B	109.5	C7X—C10X—H10F	109.5
H8A—C8—H8B	109.5	H10D—C10X—H10F	109.5
C7—C8—H8C	109.5	H10E—C10X—H10F	109.5
H8A—C8—H8C	109.5
O1—S1—N1—C1	−113.14 (17)	N1X—C1—C6—C5	−152.9 (8)
C7—S1—N1—C1	136.38 (17)	O1—S1—C7—C9	−59.63 (15)
S1—N1—C1—C6	−26.5 (3)	N1—S1—C7—C9	52.62 (15)
S1—N1—C1—C2	154.05 (16)	O1—S1—C7—C8	177.66 (12)
S1—N1—C1—N1X	−104.9 (15)	N1—S1—C7—C8	−70.09 (14)
C6—C1—C2—C3	−2.1 (3)	O1—S1—C7—C10	60.64 (17)
N1—C1—C2—C3	177.31 (18)	N1—S1—C7—C10	172.89 (16)
N1X—C1—C2—C3	149.0 (8)	C6—C1—N1X—S1X	−10.0 (16)
C1—C2—C3—O2	−177.99 (17)	C2—C1—N1X—S1X	−162.5 (9)
C1—C2—C3—C4	3.4 (3)	N1—C1—N1X—S1X	105 (2)
C4—C3—O2—C11	1.7 (3)	O1X—S1X—N1X—C1	125.7 (13)
C2—C3—O2—C11	−176.92 (19)	C7X—S1X—N1X—C1	−122.9 (14)
O2—C3—C4—C5	179.45 (19)	O1X—S1X—C7X—C8X	−178.2 (12)
C2—C3—C4—C5	−2.1 (3)	N1X—S1X—C7X—C8X	66.7 (13)
C3—C4—C5—C6	−0.5 (3)	O1X—S1X—C7X—C10X	−57.0 (15)
C4—C5—C6—C1	1.6 (3)	N1X—S1X—C7X—C10X	−172.0 (15)
C2—C1—C6—C5	−0.3 (3)	O1X—S1X—C7X—C9X	61.2 (14)
N1—C1—C6—C5	−179.7 (2)	N1X—S1X—C7X—C9X	−53.9 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.24	2.884 (2)	130
N1X—H1X···O1Xii	0.88	2.21	2.94 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.24	2.884 (2)	130
N1X—H1X⋯O1Xii	0.88	2.21	2.94 (2)	141

Symmetry codes: (i) ; (ii) .