(R)-N-(3-Meth-oxy-phen-yl)-tert-butane-sulfinamide.

The title compound, C(11)H(17)NO(2)S, was obtained by the reaction of (R)-tert-butane-sulfinamide with 3-meth-oxy-phenyl bromide in toluene. In the crystal, mol-ecules inter-act head-to-tail through N-H⋯O and C-H⋯O hydrogen bonds, forming one-dimensional chains parallel to the a axis.

Related literature

For the structure of the racemic title compound, see: Datta et al. (2010 ▶). For the structures of related N-aryl­alkanesulfinamides, see: Datta et al. (2008 ▶, 2009a ▶,b ▶). For the structures of related N-alkyl­alkanesulfinamides, see: Sato et al. (1975 ▶); Schuckmann et al. (1978 ▶); Ferreira et al. (2005 ▶).

Experimental

Crystal data

C11H17NO2S

M = 227.33

Orthorhombic,

a = 7.4418 (9) Å

b = 9.7027 (12) Å

c = 16.862 (2) Å

V = 1217.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.990, T max = 1.0

7010 measured reflections

2481 independent reflections

2062 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.092

S = 1.10

2481 reflections

204 parameters

All H-atom parameters refined

Δρmax = 0.22 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), 1029 Friedel pairs

Flack parameter: −0.02 (9)

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812006496/rz2711sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006496/rz2711Isup4.hkl

Supplementary material file. DOI: 10.1107/S1600536812006496/rz2711Isup3.cml

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

C11H17NO2S	Dx = 1.246 Mg m−3
Mr = 227.33	Melting point: 375 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2411 reflections
a = 7.4418 (9) Å	θ = 3.0–29.1°
b = 9.7027 (12) Å	µ = 0.25 mm−1
c = 16.862 (2) Å	T = 293 K
V = 1217.5 (3) Å3	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm
F(000) = 488

Oxford Diffraction Xcalibur Eos diffractometer	2481 independent reflections
Radiation source: fine-focus sealed tube	2062 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.0°
ω scans	h = −9→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→12
Tmin = 0.990, Tmax = 1.0	l = −18→21
7010 measured reflections

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)] = 0.043	All H-atom parameters refined
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0403P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2481 reflections	Δρmax = 0.22 e Å−3
204 parameters	Δρmin = −0.29 e Å−3
0 restraints	Absolute structure: Flack (1983), 1029 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.02 (9)

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
S1	−0.84124 (9)	−0.41552 (6)	−0.07783 (3)	0.04091 (18)
O1	−0.6725 (4)	0.18196 (19)	−0.18439 (11)	0.0691 (6)
O2	−1.0171 (2)	−0.39294 (19)	−0.03812 (10)	0.0543 (5)
N1	−0.7259 (3)	−0.2699 (2)	−0.08452 (13)	0.0464 (5)
C1	−0.7230 (3)	0.0498 (3)	−0.20153 (15)	0.0468 (7)
C2	−0.7075 (3)	−0.0421 (3)	−0.13905 (15)	0.0416 (6)
C3	−0.7532 (3)	−0.1789 (3)	−0.14907 (14)	0.0390 (6)
C4	−0.8154 (4)	−0.2233 (3)	−0.22198 (15)	0.0540 (7)
C5	−0.8331 (5)	−0.1298 (3)	−0.28284 (17)	0.0627 (8)
C6	−0.7857 (4)	0.0065 (3)	−0.27436 (17)	0.0561 (8)
C7	−0.6704 (6)	0.2798 (4)	−0.2476 (2)	0.0730 (10)
C8	−0.6971 (3)	−0.5045 (3)	−0.00507 (14)	0.0423 (6)
C9	−0.5083 (4)	−0.5131 (4)	−0.0392 (2)	0.0621 (8)
C10	−0.7023 (5)	−0.4311 (3)	0.07445 (17)	0.0527 (7)
C11	−0.7817 (6)	−0.6475 (3)	0.0011 (2)	0.0618 (9)
H9C	−0.509 (4)	−0.550 (3)	−0.0879 (18)	0.060 (9)*
H2	−0.667 (3)	−0.012 (2)	−0.0913 (14)	0.041 (6)*
H10A	−0.641 (4)	−0.337 (3)	0.0697 (16)	0.074 (9)*
H7B	−0.593 (4)	0.247 (3)	−0.2904 (19)	0.071 (10)*
H9B	−0.438 (5)	−0.567 (4)	−0.005 (2)	0.113 (14)*
H9A	−0.439 (4)	−0.423 (3)	−0.0417 (16)	0.065 (9)*
H5	−0.878 (4)	−0.161 (3)	−0.3324 (17)	0.060 (8)*
H6	−0.807 (4)	0.066 (3)	−0.3158 (15)	0.056 (8)*
H1	−0.692 (4)	−0.237 (2)	−0.0438 (14)	0.039 (7)*
H4	−0.845 (4)	−0.312 (3)	−0.2268 (15)	0.056 (8)*
H11C	−0.913 (5)	−0.641 (3)	0.0169 (18)	0.069 (10)*
H10C	−0.819 (4)	−0.425 (3)	0.0947 (17)	0.077 (10)*
H11A	−0.709 (4)	−0.705 (3)	0.0376 (17)	0.071 (9)*
H10B	−0.643 (4)	−0.481 (3)	0.1119 (16)	0.061 (8)*
H7A	−0.620 (5)	0.361 (4)	−0.224 (2)	0.103 (14)*
H7C	−0.793 (5)	0.285 (4)	−0.2714 (18)	0.095 (13)*
H11B	−0.775 (4)	−0.695 (3)	−0.0537 (18)	0.075 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0392 (3)	0.0430 (3)	0.0405 (3)	−0.0007 (3)	−0.0001 (3)	−0.0027 (3)
O1	0.0977 (18)	0.0545 (11)	0.0550 (11)	−0.0043 (13)	−0.0024 (13)	0.0189 (9)
O2	0.0394 (10)	0.0641 (12)	0.0594 (12)	0.0039 (10)	0.0060 (9)	0.0031 (9)
N1	0.0555 (14)	0.0464 (12)	0.0374 (12)	−0.0082 (10)	−0.0103 (12)	0.0041 (10)
C1	0.0424 (16)	0.0568 (16)	0.0414 (13)	0.0049 (12)	0.0027 (13)	0.0091 (11)
C2	0.0401 (15)	0.0520 (15)	0.0326 (13)	0.0047 (11)	0.0005 (12)	0.0048 (11)
C3	0.0304 (14)	0.0538 (14)	0.0328 (12)	0.0025 (11)	0.0020 (12)	0.0059 (10)
C4	0.061 (2)	0.0594 (17)	0.0419 (15)	−0.0038 (16)	−0.0022 (14)	−0.0001 (13)
C5	0.067 (2)	0.088 (2)	0.0333 (14)	−0.0040 (19)	−0.0088 (17)	−0.0004 (13)
C6	0.0509 (18)	0.076 (2)	0.0412 (15)	0.0086 (16)	0.0015 (14)	0.0183 (14)
C7	0.075 (3)	0.075 (2)	0.068 (2)	−0.007 (2)	0.004 (2)	0.0300 (18)
C8	0.0428 (15)	0.0392 (12)	0.0448 (14)	0.0019 (12)	−0.0018 (12)	0.0021 (10)
C9	0.0529 (19)	0.065 (2)	0.068 (2)	0.0114 (18)	0.0010 (19)	−0.0014 (18)
C10	0.0557 (19)	0.0586 (17)	0.0439 (14)	−0.0086 (15)	−0.0047 (16)	0.0064 (14)
C11	0.072 (3)	0.0414 (16)	0.072 (2)	−0.0058 (15)	−0.007 (2)	0.0048 (15)

S1—O2	1.4866 (18)	C6—H6	0.92 (3)
S1—N1	1.657 (2)	C7—H7B	0.98 (3)
S1—C8	1.844 (2)	C7—H7A	0.96 (4)
O1—C1	1.367 (3)	C7—H7C	1.00 (4)
O1—C7	1.428 (3)	C8—C9	1.521 (4)
N1—C3	1.416 (3)	C8—C10	1.519 (4)
N1—H1	0.80 (2)	C8—C11	1.527 (4)
C1—C2	1.385 (3)	C9—H9C	0.90 (3)
C1—C6	1.379 (4)	C9—H9B	0.93 (4)
C2—C3	1.381 (3)	C9—H9A	1.01 (3)
C2—H2	0.91 (2)	C10—H10A	1.02 (3)
C3—C4	1.382 (4)	C10—H10C	0.94 (3)
C4—C5	1.376 (4)	C10—H10B	0.91 (3)
C4—H4	0.90 (3)	C11—H11C	1.02 (3)
C5—C6	1.376 (4)	C11—H11A	0.99 (3)
C5—H5	0.95 (3)	C11—H11B	1.03 (3)
S1—N1—H1	116.3 (18)	C8—C9—H9C	111.4 (19)
O1—C1—C2	114.8 (2)	C8—C9—H9B	109 (2)
O1—C1—C6	124.5 (2)	C8—C9—H9A	115.9 (17)
O1—C7—H7B	109.7 (18)	C8—C10—H10A	109.8 (16)
O1—C7—H7A	104 (2)	C8—C10—H10C	112.1 (19)
O1—C7—H7C	109 (2)	C8—C10—H10B	110.3 (17)
O2—S1—N1	111.17 (12)	C8—C11—H11C	110.9 (17)
O2—S1—C8	106.35 (11)	C8—C11—H11A	109.0 (18)
N1—S1—C8	98.23 (12)	C8—C11—H11B	108.7 (17)
C1—O1—C7	118.0 (3)	C9—C8—S1	108.1 (2)
C1—C2—H2	119.6 (15)	C9—C8—C11	110.9 (3)
C1—C6—H6	122.8 (16)	C10—C8—S1	110.65 (19)
C2—C3—N1	118.0 (2)	C10—C8—C9	112.5 (3)
C2—C3—C4	119.4 (2)	C10—C8—C11	110.8 (2)
C3—N1—S1	120.62 (19)	C11—C8—S1	103.4 (2)
C3—N1—H1	117.4 (17)	H9C—C9—H9B	110 (3)
C3—C2—C1	120.3 (2)	H9C—C9—H9A	108 (3)
C3—C2—H2	120.1 (15)	H10A—C10—H10C	113 (3)
C3—C4—H4	117.5 (17)	H10A—C10—H10B	108 (2)
C4—C3—N1	122.5 (2)	H7B—C7—H7A	110 (3)
C4—C5—C6	122.1 (3)	H7B—C7—H7C	105 (3)
C4—C5—H5	118.5 (17)	H9B—C9—H9A	103 (3)
C5—C4—C3	119.4 (3)	H11C—C11—H11A	114 (3)
C5—C4—H4	123.1 (17)	H11C—C11—H11B	108 (3)
C5—C6—C1	118.2 (3)	H10C—C10—H10B	103 (2)
C5—C6—H6	118.8 (16)	H11A—C11—H11B	106 (2)
C6—C1—C2	120.6 (3)	H7A—C7—H7C	119 (3)
C6—C5—H5	119.4 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.80 (2)	2.28 (3)	3.031 (3)	157 (2)
C10—H10A···O2i	1.02 (3)	2.47 (3)	3.487 (4)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.80 (2)	2.28 (3)	3.031 (3)	157 (2)
C10—H10A⋯O2i	1.02 (3)	2.47 (3)	3.487 (4)	171 (2)

Symmetry code: (i) .