(S)-N-Phenyl-tert-butane-sulfinamide.

The asymmetric unit of the title compound, C(10)H(15)NOS, contains two independent mol-ecules with similar conformations. In the crystal, mol-ecules are linked in a head-to-tail fashion by N-H⋯O hydrogen bonds into chains running along the b axis. The absolute configuration was assigned on the basis of known chirality of the parent compound.

Related literature

For the structures of related N-alkyl and N-aryl alkanesulf­in­amides, see: Datta et al. (2008 ▶, 2009a ▶,b ▶, 2010 ▶); Sun et al. (2012a ▶,b ▶) Zhang et al. (2012 ▶); Sato et al. (1975 ▶); Schuckmann et al. (1978 ▶); Ferreira et al. (2005 ▶).

Experimental

Crystal data

C10H15NOS

M = 197.29

Orthorhombic,

a = 9.3596 (4) Å

b = 10.4702 (4) Å

c = 22.7438 (10) Å

V = 2228.82 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.38 × 0.32 × 0.30 mm

Data collection

Aglenet Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.987, T max = 1.000

6065 measured reflections

3993 independent reflections

2503 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.090

S = 0.98

3993 reflections

249 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 1390 Friedel pairs

Flack parameter: −0.09 (9)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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/S1600536812020673/rz2751sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020673/rz2751Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020673/rz2751Isup3.cml

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

C10H15NOS	Dx = 1.176 Mg m−3
Mr = 197.29	Melting point = 383–386 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7107 Å
a = 9.3596 (4) Å	Cell parameters from 1915 reflections
b = 10.4702 (4) Å	θ = 3.1–29.1°
c = 22.7438 (10) Å	µ = 0.25 mm−1
V = 2228.82 (17) Å3	T = 293 K
Z = 8	Block, colourless
F(000) = 848	0.38 × 0.32 × 0.30 mm

Aglenet Xcalibur Eos diffractometer	3993 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2503 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −11→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→10
Tmin = 0.987, Tmax = 1.000	l = −16→28
6065 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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0271P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max = 0.001
3993 reflections	Δρmax = 0.26 e Å−3
249 parameters	Δρmin = −0.26 e Å−3
0 restraints	Absolute structure: Flack (1983), 1390 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.09 (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	−0.63522 (11)	−0.88887 (8)	−0.08184 (4)	0.0658 (3)
S2	0.04812 (9)	−1.49605 (8)	0.25283 (4)	0.0596 (2)
O1	−0.6196 (3)	−0.7833 (2)	−0.12453 (11)	0.0943 (9)
O2	0.0446 (3)	−1.3883 (2)	0.20975 (9)	0.0730 (7)
N1	−0.5152 (4)	−0.9991 (3)	−0.09407 (14)	0.0781 (10)
H1	−0.517 (3)	−1.037 (2)	−0.1245 (12)	0.051 (11)*
N2	0.0029 (4)	−1.4435 (3)	0.31882 (13)	0.0702 (10)
H2	0.042 (3)	−1.376 (2)	0.3290 (11)	0.038 (9)*
C1	−0.3963 (4)	−1.0169 (3)	−0.05740 (14)	0.0567 (9)
C2	−0.3226 (4)	−1.1295 (3)	−0.06151 (15)	0.0697 (11)
H2A	−0.3507	−1.1910	−0.0887	0.084*
C3	−0.2065 (5)	−1.1521 (4)	−0.02543 (17)	0.0783 (12)
H3	−0.1560	−1.2283	−0.0289	0.094*
C4	−0.1653 (5)	−1.0632 (5)	0.01535 (16)	0.0814 (13)
H4	−0.0881	−1.0792	0.0400	0.098*
C5	−0.2383 (5)	−0.9517 (4)	0.01931 (17)	0.0805 (12)
H5	−0.2106	−0.8912	0.0470	0.097*
C6	−0.3530 (5)	−0.9262 (3)	−0.01707 (15)	0.0683 (11)
H6	−0.4007	−0.8485	−0.0144	0.082*
C7	−0.7985 (4)	−0.9729 (3)	−0.10372 (14)	0.0651 (10)
C8	−0.7966 (4)	−0.9995 (4)	−0.17018 (14)	0.0892 (12)
H8A	−0.7820	−0.9209	−0.1911	0.134*
H8B	−0.8861	−1.0365	−0.1818	0.134*
H8C	−0.7204	−1.0577	−0.1792	0.134*
C9	−0.9184 (4)	−0.8808 (3)	−0.08820 (16)	0.0868 (12)
H9A	−0.9160	−0.8631	−0.0468	0.130*
H9B	−1.0086	−0.9185	−0.0982	0.130*
H9C	−0.9061	−0.8027	−0.1097	0.130*
C10	−0.8088 (4)	−1.0947 (3)	−0.06758 (17)	0.1018 (15)
H10A	−0.7340	−1.1523	−0.0790	0.153*
H10B	−0.8999	−1.1343	−0.0743	0.153*
H10C	−0.7991	−1.0744	−0.0266	0.153*
C11	−0.1317 (4)	−1.4709 (3)	0.34283 (13)	0.0549 (9)
C12	−0.2013 (4)	−1.5837 (3)	0.33049 (14)	0.0687 (11)
H12	−0.1604	−1.6432	0.3052	0.082*
C13	−0.3322 (4)	−1.6075 (4)	0.35607 (17)	0.0791 (11)
H13	−0.3804	−1.6823	0.3466	0.095*
C14	−0.3932 (4)	−1.5244 (5)	0.39494 (17)	0.0868 (13)
H14	−0.4807	−1.5427	0.4123	0.104*
C15	−0.3220 (4)	−1.4137 (4)	0.40762 (16)	0.0815 (13)
H15	−0.3619	−1.3566	0.4343	0.098*
C16	−0.1937 (4)	−1.3846 (3)	0.38212 (14)	0.0705 (10)
H16	−0.1481	−1.3080	0.3909	0.085*
C17	0.2373 (4)	−1.5304 (3)	0.26576 (14)	0.0632 (10)
C18	0.2876 (5)	−1.5848 (4)	0.20743 (18)	0.1162 (16)
H18A	0.2232	−1.6508	0.1950	0.174*
H18B	0.3817	−1.6199	0.2120	0.174*
H18C	0.2898	−1.5182	0.1785	0.174*
C19	0.3190 (4)	−1.4111 (3)	0.28162 (15)	0.0825 (12)
H19A	0.3082	−1.3490	0.2509	0.124*
H19B	0.4184	−1.4314	0.2863	0.124*
H19C	0.2825	−1.3768	0.3178	0.124*
C20	0.2443 (5)	−1.6306 (4)	0.31436 (17)	0.1057 (15)
H20A	0.2186	−1.5922	0.3512	0.159*
H20B	0.3397	−1.6639	0.3169	0.159*
H20C	0.1791	−1.6988	0.3056	0.159*

	U11	U22	U33	U12	U13	U23
S1	0.0774 (6)	0.0593 (5)	0.0608 (5)	0.0046 (6)	0.0068 (6)	−0.0011 (5)
S2	0.0663 (5)	0.0637 (5)	0.0488 (4)	−0.0082 (6)	0.0024 (5)	−0.0111 (5)
O1	0.102 (2)	0.0703 (15)	0.1102 (19)	−0.0104 (17)	0.011 (2)	0.0274 (15)
O2	0.0870 (17)	0.0736 (15)	0.0582 (14)	0.0001 (18)	−0.0085 (15)	0.0076 (12)
N1	0.087 (2)	0.092 (2)	0.0550 (19)	0.022 (2)	−0.005 (2)	−0.027 (2)
N2	0.078 (2)	0.071 (2)	0.0618 (19)	−0.024 (2)	0.0131 (19)	−0.0221 (17)
C1	0.067 (2)	0.060 (2)	0.0430 (18)	0.001 (2)	0.0080 (18)	−0.0012 (18)
C2	0.078 (3)	0.067 (3)	0.063 (2)	0.000 (3)	0.003 (2)	−0.0006 (19)
C3	0.082 (3)	0.075 (3)	0.078 (3)	0.017 (3)	0.013 (3)	0.010 (2)
C4	0.077 (3)	0.106 (3)	0.061 (3)	0.002 (3)	−0.003 (3)	0.012 (3)
C5	0.094 (3)	0.088 (3)	0.059 (3)	−0.011 (3)	0.002 (3)	−0.004 (2)
C6	0.087 (3)	0.066 (2)	0.052 (2)	−0.002 (3)	0.007 (2)	0.0038 (19)
C7	0.072 (3)	0.054 (2)	0.069 (2)	0.004 (2)	0.009 (2)	0.0059 (18)
C8	0.087 (3)	0.102 (3)	0.078 (3)	0.004 (3)	−0.009 (3)	−0.017 (2)
C9	0.076 (3)	0.083 (3)	0.101 (3)	0.011 (3)	0.014 (3)	−0.004 (2)
C10	0.116 (4)	0.073 (3)	0.117 (3)	−0.010 (3)	0.024 (3)	0.021 (2)
C11	0.062 (2)	0.057 (2)	0.0462 (19)	−0.001 (2)	0.000 (2)	0.0024 (17)
C12	0.068 (3)	0.073 (3)	0.065 (2)	0.001 (2)	0.012 (2)	−0.0014 (19)
C13	0.071 (3)	0.082 (3)	0.084 (3)	−0.009 (3)	0.007 (3)	0.004 (2)
C14	0.065 (3)	0.117 (3)	0.079 (3)	0.010 (3)	0.014 (2)	0.017 (3)
C15	0.081 (3)	0.097 (3)	0.066 (3)	0.027 (3)	0.017 (3)	−0.004 (2)
C16	0.086 (3)	0.070 (2)	0.055 (2)	0.012 (3)	0.008 (2)	−0.004 (2)
C17	0.068 (2)	0.063 (2)	0.058 (2)	0.002 (2)	0.001 (2)	−0.0055 (18)
C18	0.091 (3)	0.150 (4)	0.107 (3)	0.016 (3)	0.013 (3)	−0.052 (3)
C19	0.071 (3)	0.078 (3)	0.098 (3)	−0.009 (2)	−0.004 (2)	−0.002 (2)
C20	0.105 (3)	0.084 (3)	0.128 (4)	0.000 (3)	−0.019 (3)	0.025 (3)

S1—O1	1.479 (2)	C9—H9B	0.9600
S1—N1	1.634 (3)	C9—H9C	0.9600
S1—C7	1.832 (4)	C10—H10A	0.9600
S2—O2	1.494 (2)	C10—H10B	0.9600
S2—N2	1.654 (3)	C10—H10C	0.9600
S2—C17	1.831 (4)	C11—C12	1.378 (4)
N1—H1	0.80 (3)	C11—C16	1.397 (4)
N1—C1	1.403 (4)	C12—H12	0.9300
N2—H2	0.83 (2)	C12—C13	1.379 (5)
N2—C11	1.403 (4)	C13—H13	0.9300
C1—C2	1.370 (4)	C13—C14	1.365 (5)
C1—C6	1.381 (4)	C14—H14	0.9300
C2—H2A	0.9300	C14—C15	1.368 (5)
C2—C3	1.382 (5)	C15—H15	0.9300
C3—H3	0.9300	C15—C16	1.368 (5)
C3—C4	1.370 (5)	C16—H16	0.9300
C4—H4	0.9300	C17—C18	1.519 (4)
C4—C5	1.356 (5)	C17—C19	1.509 (4)
C5—H5	0.9300	C17—C20	1.526 (4)
C5—C6	1.381 (5)	C18—H18A	0.9600
C6—H6	0.9300	C18—H18B	0.9600
C7—C8	1.537 (4)	C18—H18C	0.9600
C7—C9	1.521 (4)	C19—H19A	0.9600
C7—C10	1.520 (4)	C19—H19B	0.9600
C8—H8A	0.9600	C19—H19C	0.9600
C8—H8B	0.9600	C20—H20A	0.9600
C8—H8C	0.9600	C20—H20B	0.9600
C9—H9A	0.9600	C20—H20C	0.9600
O1—S1—N1	110.38 (17)	C7—C10—H10A	109.5
O1—S1—C7	105.27 (16)	C7—C10—H10B	109.5
N1—S1—C7	100.83 (16)	C7—C10—H10C	109.5
O2—S2—N2	109.77 (14)	H10A—C10—H10B	109.5
O2—S2—C17	105.97 (15)	H10A—C10—H10C	109.5
N2—S2—C17	99.62 (16)	H10B—C10—H10C	109.5
S1—N1—H1	119 (2)	C12—C11—N2	121.4 (3)
C1—N1—S1	122.5 (3)	C12—C11—C16	119.3 (4)
C1—N1—H1	118 (2)	C16—C11—N2	119.3 (3)
S2—N2—H2	115.2 (19)	C11—C12—H12	120.4
C11—N2—S2	121.0 (3)	C11—C12—C13	119.2 (4)
C11—N2—H2	117.5 (19)	C13—C12—H12	120.4
C2—C1—N1	118.3 (3)	C12—C13—H13	119.0
C2—C1—C6	119.3 (3)	C14—C13—C12	122.0 (4)
C6—C1—N1	122.5 (4)	C14—C13—H13	119.0
C1—C2—H2A	119.9	C13—C14—H14	120.9
C1—C2—C3	120.2 (4)	C13—C14—C15	118.2 (4)
C3—C2—H2A	119.9	C15—C14—H14	120.9
C2—C3—H3	119.8	C14—C15—H15	119.1
C4—C3—C2	120.5 (4)	C14—C15—C16	121.8 (4)
C4—C3—H3	119.8	C16—C15—H15	119.1
C3—C4—H4	120.4	C11—C16—H16	120.3
C5—C4—C3	119.2 (4)	C15—C16—C11	119.4 (4)
C5—C4—H4	120.4	C15—C16—H16	120.3
C4—C5—H5	119.4	C18—C17—S2	103.5 (2)
C4—C5—C6	121.2 (4)	C18—C17—C20	111.2 (3)
C6—C5—H5	119.4	C19—C17—S2	111.5 (2)
C1—C6—C5	119.6 (4)	C19—C17—C18	111.3 (3)
C1—C6—H6	120.2	C19—C17—C20	112.0 (3)
C5—C6—H6	120.2	C20—C17—S2	107.0 (3)
C8—C7—S1	110.1 (3)	C17—C18—H18A	109.5
C9—C7—S1	104.3 (2)	C17—C18—H18B	109.5
C9—C7—C8	110.6 (3)	C17—C18—H18C	109.5
C10—C7—S1	108.0 (3)	H18A—C18—H18B	109.5
C10—C7—C8	112.4 (3)	H18A—C18—H18C	109.5
C10—C7—C9	111.1 (3)	H18B—C18—H18C	109.5
C7—C8—H8A	109.5	C17—C19—H19A	109.5
C7—C8—H8B	109.5	C17—C19—H19B	109.5
C7—C8—H8C	109.5	C17—C19—H19C	109.5
H8A—C8—H8B	109.5	H19A—C19—H19B	109.5
H8A—C8—H8C	109.5	H19A—C19—H19C	109.5
H8B—C8—H8C	109.5	H19B—C19—H19C	109.5
C7—C9—H9A	109.5	C17—C20—H20A	109.5
C7—C9—H9B	109.5	C17—C20—H20B	109.5
C7—C9—H9C	109.5	C17—C20—H20C	109.5
H9A—C9—H9B	109.5	H20A—C20—H20B	109.5
H9A—C9—H9C	109.5	H20A—C20—H20C	109.5
H9B—C9—H9C	109.5	H20B—C20—H20C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.80 (3)	2.17 (3)	2.937 (4)	161 (3)
N2—H2···O1ii	0.83 (2)	2.11 (2)	2.914 (4)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.80 (3)	2.17 (3)	2.937 (4)	161 (3)
N2—H2⋯O1ii	0.83 (2)	2.11 (2)	2.914 (4)	166 (3)

Symmetry codes: (i) ; (ii) .