N-(4-Methoxy-phen-yl)-tert-butane-sulfinamide.

In the title compound, C(11)H(17)NO(2)S, the mol-ecules inter-act head-to-tail through N-H⋯OS hydrogen bonds, giving discrete centrosymmetric cyclic dimers. The N-C(ar-yl) bond length [1.4225 (14) Å] is inter-mediate between that in N-phenyl-tert-butane-sulfinamide [1.4083 (12) Å] and the N-C(alk-yl) bond lengths in N-alkyl-alkanesulfinamides (1.470-1.530 Å), suggesting weaker delocalization of electrons over the N atom and the aromatic ring due to the presence of the 4-meth-oxy group.

Related literature

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

Experimental

Crystal data

C11H17NO2S

M = 227.32

Orthorhombic,

a = 19.6157 (11) Å

b = 9.1034 (5) Å

c = 13.3808 (7) Å

V = 2389.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 150 K

0.70 × 0.37 × 0.33 mm

Data collection

Bruker APEXII CCD-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 2007 ▶) T min = 0.843, T max = 0.921

26681 measured reflections

3659 independent reflections

3027 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.108

S = 1.05

3659 reflections

144 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.38 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/S1600536809042548/zs2015sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042548/zs2015Isup2.hkl

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

C11H17NO2S	Dx = 1.264 Mg m−3
Mr = 227.32	Melting point: 384 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6992 reflections
a = 19.6157 (11) Å	θ = 2.5–30.4°
b = 9.1034 (5) Å	µ = 0.25 mm−1
c = 13.3808 (7) Å	T = 150 K
V = 2389.4 (2) Å3	Block, colourless
Z = 8	0.70 × 0.37 × 0.33 mm
F(000) = 976

Bruker APEXII CCD-detector diffractometer	3659 independent reflections
Radiation source: fine-focus sealed tube	3027 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω rotation with narrow frames scans	θmax = 30.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −27→27
Tmin = 0.843, Tmax = 0.921	k = −13→12
26681 measured reflections	l = −18→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.5032P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.108	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.37 e Å−3
3659 reflections	Δρmin = −0.38 e Å−3
144 parameters	Extinction correction: SHELXL97>/i> (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0049 (8)
Primary atom site location: structure-invariant direct methods

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
O1	0.55068 (4)	1.13801 (9)	0.06229 (6)	0.02755 (19)
S1	0.613894 (14)	1.06197 (3)	0.02673 (2)	0.02307 (10)
N1	0.59358 (6)	0.89272 (11)	−0.01268 (8)	0.0256 (2)
H1	0.5522 (8)	0.8854 (16)	−0.0349 (11)	0.031*
C1	0.61179 (5)	0.77090 (13)	0.04831 (8)	0.0229 (2)
C2	0.56489 (6)	0.65860 (12)	0.06430 (9)	0.0258 (2)
H2	0.5208	0.6652	0.0353	0.031*
C3	0.58165 (6)	0.53688 (13)	0.12200 (9)	0.0281 (2)
H3	0.5491	0.4613	0.1328	0.034*
C4	0.64632 (6)	0.52643 (13)	0.16383 (9)	0.0283 (2)
C5	0.69388 (6)	0.63664 (14)	0.14644 (9)	0.0302 (3)
H5	0.7383	0.6288	0.1743	0.036*
C6	0.67709 (6)	0.75779 (13)	0.08881 (9)	0.0275 (2)
H6	0.7101	0.8321	0.0768	0.033*
O2	0.66770 (5)	0.41138 (10)	0.22206 (8)	0.0405 (2)
C11	0.61629 (8)	0.32282 (15)	0.26749 (11)	0.0421 (3)
H11A	0.5832	0.3862	0.3014	0.063*
H11B	0.6374	0.2565	0.3162	0.063*
H11C	0.5930	0.2650	0.2160	0.063*
C7	0.63507 (6)	1.14369 (12)	−0.09505 (8)	0.0251 (2)
C8	0.57849 (6)	1.11814 (14)	−0.17123 (9)	0.0296 (2)
H8A	0.5877	1.1761	−0.2314	0.044*
H8B	0.5347	1.1482	−0.1425	0.044*
H8C	0.5767	1.0137	−0.1887	0.044*
C9	0.70236 (7)	1.07343 (15)	−0.12670 (11)	0.0351 (3)
H9A	0.6963	0.9670	−0.1330	0.053*
H9B	0.7373	1.0941	−0.0763	0.053*
H9C	0.7167	1.1142	−0.1912	0.053*
C10	0.64515 (7)	1.30746 (13)	−0.07418 (10)	0.0321 (3)
H10A	0.6645	1.3551	−0.1334	0.048*
H10B	0.6763	1.3198	−0.0175	0.048*
H10C	0.6011	1.3525	−0.0582	0.048*

	U11	U22	U33	U12	U13	U23
O1	0.0260 (4)	0.0291 (4)	0.0275 (4)	0.0000 (3)	0.0027 (3)	−0.0045 (3)
S1	0.02289 (15)	0.02413 (15)	0.02218 (15)	−0.00033 (9)	−0.00198 (9)	−0.00084 (9)
N1	0.0277 (5)	0.0220 (4)	0.0272 (5)	0.0001 (4)	−0.0057 (4)	0.0009 (4)
C1	0.0246 (5)	0.0237 (5)	0.0205 (5)	0.0034 (4)	0.0007 (4)	−0.0007 (4)
C2	0.0238 (5)	0.0256 (5)	0.0279 (5)	0.0019 (4)	−0.0032 (4)	−0.0012 (4)
C3	0.0282 (6)	0.0250 (5)	0.0310 (6)	−0.0009 (4)	−0.0030 (4)	0.0013 (4)
C4	0.0305 (6)	0.0272 (5)	0.0272 (5)	0.0059 (5)	−0.0021 (4)	0.0017 (4)
C5	0.0229 (5)	0.0366 (6)	0.0310 (6)	0.0059 (5)	−0.0022 (4)	0.0030 (5)
C6	0.0220 (5)	0.0309 (6)	0.0295 (6)	0.0003 (4)	0.0022 (4)	0.0028 (4)
O2	0.0408 (5)	0.0357 (5)	0.0451 (6)	0.0047 (4)	−0.0105 (4)	0.0147 (4)
C11	0.0590 (9)	0.0309 (6)	0.0363 (7)	−0.0034 (6)	−0.0074 (6)	0.0087 (5)
C7	0.0251 (5)	0.0245 (5)	0.0256 (5)	−0.0002 (4)	0.0021 (4)	0.0009 (4)
C8	0.0336 (6)	0.0314 (6)	0.0238 (5)	−0.0004 (5)	−0.0017 (4)	0.0017 (4)
C9	0.0274 (6)	0.0388 (7)	0.0392 (7)	0.0021 (5)	0.0070 (5)	−0.0028 (5)
C10	0.0339 (6)	0.0266 (5)	0.0358 (6)	−0.0045 (5)	0.0021 (5)	0.0007 (5)

O1—S1	1.4977 (9)	O2—C11	1.4271 (18)
S1—N1	1.6765 (10)	C11—H11A	0.9800
S1—C7	1.8388 (11)	C11—H11B	0.9800
N1—C1	1.4225 (14)	C11—H11C	0.9800
N1—H1	0.867 (16)	C7—C8	1.5246 (16)
C1—C2	1.3919 (16)	C7—C9	1.5267 (17)
C1—C6	1.3960 (16)	C7—C10	1.5296 (16)
C2—C3	1.3900 (16)	C8—H8A	0.9800
C2—H2	0.9500	C8—H8B	0.9800
C3—C4	1.3897 (17)	C8—H8C	0.9800
C3—H3	0.9500	C9—H9A	0.9800
C4—O2	1.3711 (14)	C9—H9B	0.9800
C4—C5	1.3896 (18)	C9—H9C	0.9800
C5—C6	1.3854 (16)	C10—H10A	0.9800
C5—H5	0.9500	C10—H10B	0.9800
C6—H6	0.9500	C10—H10C	0.9800
O1—S1—N1	109.15 (5)	O2—C11—H11C	109.5
O1—S1—C7	106.35 (5)	H11A—C11—H11C	109.5
N1—S1—C7	98.44 (5)	H11B—C11—H11C	109.5
C1—N1—S1	118.44 (8)	C8—C7—C9	112.33 (10)
C1—N1—H1	111.8 (10)	C8—C7—C10	111.40 (10)
S1—N1—H1	113.7 (10)	C9—C7—C10	110.31 (10)
C2—C1—C6	118.95 (11)	C8—C7—S1	111.49 (8)
C2—C1—N1	119.66 (10)	C9—C7—S1	105.76 (8)
C6—C1—N1	121.32 (11)	C10—C7—S1	105.17 (8)
C3—C2—C1	120.96 (11)	C7—C8—H8A	109.5
C3—C2—H2	119.5	C7—C8—H8B	109.5
C1—C2—H2	119.5	H8A—C8—H8B	109.5
C4—C3—C2	119.62 (11)	C7—C8—H8C	109.5
C4—C3—H3	120.2	H8A—C8—H8C	109.5
C2—C3—H3	120.2	H8B—C8—H8C	109.5
O2—C4—C5	116.18 (11)	C7—C9—H9A	109.5
O2—C4—C3	124.09 (11)	C7—C9—H9B	109.5
C5—C4—C3	119.73 (11)	H9A—C9—H9B	109.5
C6—C5—C4	120.56 (11)	C7—C9—H9C	109.5
C6—C5—H5	119.7	H9A—C9—H9C	109.5
C4—C5—H5	119.7	H9B—C9—H9C	109.5
C5—C6—C1	120.14 (11)	C7—C10—H10A	109.5
C5—C6—H6	119.9	C7—C10—H10B	109.5
C1—C6—H6	119.9	H10A—C10—H10B	109.5
C4—O2—C11	117.22 (11)	C7—C10—H10C	109.5
O2—C11—H11A	109.5	H10A—C10—H10C	109.5
O2—C11—H11B	109.5	H10B—C10—H10C	109.5
H11A—C11—H11B	109.5
O1—S1—N1—C1	−106.05 (9)	C4—C5—C6—C1	0.60 (19)
C7—S1—N1—C1	143.29 (9)	C2—C1—C6—C5	−1.93 (17)
S1—N1—C1—C2	135.83 (10)	N1—C1—C6—C5	−178.79 (11)
S1—N1—C1—C6	−47.33 (14)	C5—C4—O2—C11	160.40 (12)
C6—C1—C2—C3	1.88 (17)	C3—C4—O2—C11	−20.22 (18)
N1—C1—C2—C3	178.79 (11)	O1—S1—C7—C8	−61.74 (9)
C1—C2—C3—C4	−0.47 (18)	N1—S1—C7—C8	51.16 (9)
C2—C3—C4—O2	179.75 (12)	O1—S1—C7—C9	175.89 (8)
C2—C3—C4—C5	−0.89 (18)	N1—S1—C7—C9	−71.21 (9)
O2—C4—C5—C6	−179.76 (11)	O1—S1—C7—C10	59.13 (9)
C3—C4—C5—C6	0.83 (19)	N1—S1—C7—C10	172.03 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.867 (16)	2.062 (17)	2.9201 (14)	170.1 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.867 (16)	2.062 (17)	2.9201 (14)	170.1 (14)

Symmetry code: (i) .