N-Phenyl-tert-butane-sulfinamide.

In the racemic title compound, C(10)H(15)NOS, the packing exhibits centrosymmetric pairs of mol-ecules linked by N-H⋯O=S hydrogen bonds in a head-to-tail fashion. The N-C(ar-yl) bond [1.4083 (12) Å] is considerably shorter than the N-C(alk-yl) bonds typically found in N-alkyl-alkanesulfinamides (1.470-1.530 Å).

Related literature

For N-aryl­alkanesulfinamides, see: Datta et al. (2008 ▶) and for cyclic N-aryl­alkanesulfinamides (sultims), see: Schulze et al. (2005 ▶). 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

C10H15NOS

M = 197.29

Monoclinic,

a = 7.4822 (3) Å

b = 15.7881 (6) Å

c = 8.8333 (4) Å

β = 99.3865 (6)°

V = 1029.50 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 150 K

0.54 × 0.49 × 0.39 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.866, T max = 0.900

12022 measured reflections

3150 independent reflections

2861 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.05

3150 reflections

125 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.36 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/S1600536809028633/zs2002sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028633/zs2002Isup2.hkl

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

C10H15NOS	F(000) = 424
Mr = 197.29	Dx = 1.273 Mg m−3
Monoclinic, P21/c	Melting point = 376–377 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.4822 (3) Å	Cell parameters from 6597 reflections
b = 15.7881 (6) Å	θ = 2.3–30.5°
c = 8.8333 (4) Å	µ = 0.28 mm−1
β = 99.3865 (6)°	T = 150 K
V = 1029.50 (7) Å3	Block, colourless
Z = 4	0.54 × 0.49 × 0.39 mm

Bruker APEXII CCD diffractometer	3150 independent reflections
Radiation source: fine-focus sealed tube	2861 reflections with I > 2σ(I)
graphite	Rint = 0.020
ω rotation with narrow frames scans	θmax = 30.6°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −10→10
Tmin = 0.866, Tmax = 0.900	k = −22→22
12022 measured reflections	l = −12→12

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0516P)2 + 0.2529P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
3150 reflections	Δρmax = 0.38 e Å−3
125 parameters	Δρmin = −0.36 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (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
O1	−0.06049 (10)	0.60738 (4)	0.41648 (9)	0.02295 (16)
S1	0.10835 (3)	0.601595 (13)	0.34614 (3)	0.01896 (9)
N1	0.17155 (13)	0.50050 (5)	0.35165 (10)	0.02446 (18)
H1	0.1463 (19)	0.4727 (9)	0.4219 (15)	0.029*
C1	0.19492 (12)	0.45439 (6)	0.21979 (11)	0.01998 (18)
C2	0.24483 (16)	0.49296 (7)	0.09080 (12)	0.0281 (2)
H2	0.2589	0.5527	0.0877	0.034*
C3	0.27381 (17)	0.44344 (7)	−0.03327 (13)	0.0318 (2)
H3	0.3053	0.4700	−0.1218	0.038*
C4	0.25757 (15)	0.35617 (7)	−0.02991 (13)	0.0295 (2)
H4	0.2790	0.3230	−0.1148	0.035*
C5	0.20955 (14)	0.31769 (6)	0.09922 (12)	0.0257 (2)
H5	0.1990	0.2578	0.1029	0.031*
C6	0.17690 (13)	0.36629 (6)	0.22303 (11)	0.02134 (18)
H6	0.1422	0.3396	0.3101	0.026*
C7	0.29072 (13)	0.64579 (6)	0.48984 (11)	0.02172 (18)
C8	0.24368 (16)	0.73950 (7)	0.50283 (14)	0.0316 (2)
H8A	0.3444	0.7687	0.5668	0.047*
H8B	0.1342	0.7448	0.5497	0.047*
H8C	0.2223	0.7650	0.4003	0.047*
C9	0.46486 (15)	0.63537 (8)	0.42278 (14)	0.0312 (2)
H9A	0.5658	0.6613	0.4919	0.047*
H9B	0.4512	0.6632	0.3224	0.047*
H9C	0.4894	0.5750	0.4110	0.047*
C10	0.30068 (15)	0.60073 (6)	0.64357 (12)	0.0265 (2)
H10A	0.3290	0.5408	0.6314	0.040*
H10B	0.1839	0.6057	0.6794	0.040*
H10C	0.3956	0.6267	0.7188	0.040*

	U11	U22	U33	U12	U13	U23
O1	0.0218 (3)	0.0215 (3)	0.0264 (4)	0.0011 (2)	0.0067 (3)	0.0021 (2)
S1	0.02263 (13)	0.01561 (12)	0.01895 (13)	0.00052 (7)	0.00429 (8)	0.00155 (7)
N1	0.0397 (5)	0.0153 (3)	0.0206 (4)	0.0013 (3)	0.0114 (3)	0.0012 (3)
C1	0.0214 (4)	0.0187 (4)	0.0202 (4)	0.0003 (3)	0.0045 (3)	−0.0011 (3)
C2	0.0397 (6)	0.0210 (4)	0.0254 (5)	−0.0014 (4)	0.0112 (4)	0.0010 (4)
C3	0.0422 (6)	0.0327 (6)	0.0224 (5)	0.0011 (4)	0.0111 (4)	0.0006 (4)
C4	0.0324 (5)	0.0316 (5)	0.0251 (5)	0.0014 (4)	0.0063 (4)	−0.0080 (4)
C5	0.0247 (5)	0.0218 (4)	0.0304 (5)	−0.0010 (3)	0.0043 (4)	−0.0060 (4)
C6	0.0207 (4)	0.0186 (4)	0.0252 (4)	−0.0012 (3)	0.0053 (3)	−0.0006 (3)
C7	0.0218 (4)	0.0186 (4)	0.0242 (4)	0.0006 (3)	0.0022 (3)	−0.0001 (3)
C8	0.0352 (5)	0.0183 (4)	0.0387 (6)	−0.0002 (4)	−0.0013 (4)	−0.0037 (4)
C9	0.0230 (5)	0.0366 (6)	0.0346 (6)	0.0004 (4)	0.0065 (4)	0.0042 (4)
C10	0.0290 (5)	0.0278 (5)	0.0220 (5)	0.0026 (4)	0.0020 (4)	0.0006 (3)

O1—S1	1.4988 (7)	C5—H5	0.9500
S1—N1	1.6632 (9)	C6—H6	0.9500
S1—C7	1.8426 (10)	C7—C10	1.5241 (14)
N1—C1	1.4083 (12)	C7—C9	1.5255 (14)
N1—H1	0.808 (12)	C7—C8	1.5294 (14)
C1—C2	1.3954 (13)	C8—H8A	0.9800
C1—C6	1.3982 (12)	C8—H8B	0.9800
C2—C3	1.3918 (15)	C8—H8C	0.9800
C2—H2	0.9500	C9—H9A	0.9800
C3—C4	1.3838 (17)	C9—H9B	0.9800
C3—H3	0.9500	C9—H9C	0.9800
C4—C5	1.3903 (15)	C10—H10A	0.9800
C4—H4	0.9500	C10—H10B	0.9800
C5—C6	1.3898 (13)	C10—H10C	0.9800
O1—S1—N1	107.53 (4)	C10—C7—C9	112.02 (8)
O1—S1—C7	105.72 (4)	C10—C7—C8	111.29 (9)
N1—S1—C7	99.69 (5)	C9—C7—C8	110.80 (9)
C1—N1—S1	123.02 (7)	C10—C7—S1	111.11 (7)
C1—N1—H1	115.5 (10)	C9—C7—S1	105.97 (7)
S1—N1—H1	116.3 (10)	C8—C7—S1	105.33 (7)
C2—C1—C6	119.36 (9)	C7—C8—H8A	109.5
C2—C1—N1	122.39 (8)	C7—C8—H8B	109.5
C6—C1—N1	118.16 (8)	H8A—C8—H8B	109.5
C3—C2—C1	119.65 (10)	C7—C8—H8C	109.5
C3—C2—H2	120.2	H8A—C8—H8C	109.5
C1—C2—H2	120.2	H8B—C8—H8C	109.5
C4—C3—C2	121.12 (10)	C7—C9—H9A	109.5
C4—C3—H3	119.4	C7—C9—H9B	109.5
C2—C3—H3	119.4	H9A—C9—H9B	109.5
C3—C4—C5	119.21 (9)	C7—C9—H9C	109.5
C3—C4—H4	120.4	H9A—C9—H9C	109.5
C5—C4—H4	120.4	H9B—C9—H9C	109.5
C6—C5—C4	120.43 (9)	C7—C10—H10A	109.5
C6—C5—H5	119.8	C7—C10—H10B	109.5
C4—C5—H5	119.8	H10A—C10—H10B	109.5
C5—C6—C1	120.21 (9)	C7—C10—H10C	109.5
C5—C6—H6	119.9	H10A—C10—H10C	109.5
C1—C6—H6	119.9	H10B—C10—H10C	109.5
O1—S1—N1—C1	123.13 (8)	C4—C5—C6—C1	−1.02 (15)
C7—S1—N1—C1	−126.86 (8)	C2—C1—C6—C5	0.40 (14)
S1—N1—C1—C2	28.58 (14)	N1—C1—C6—C5	−176.09 (9)
S1—N1—C1—C6	−155.05 (8)	O1—S1—C7—C10	54.89 (8)
C6—C1—C2—C3	0.76 (16)	N1—S1—C7—C10	−56.55 (8)
N1—C1—C2—C3	177.09 (10)	O1—S1—C7—C9	176.79 (7)
C1—C2—C3—C4	−1.32 (18)	N1—S1—C7—C9	65.35 (7)
C2—C3—C4—C5	0.70 (17)	O1—S1—C7—C8	−65.73 (8)
C3—C4—C5—C6	0.48 (16)	N1—S1—C7—C8	−177.17 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.81 (1)	2.09 (1)	2.8882 (11)	173 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.808 (12)	2.085 (12)	2.8882 (11)	173.1 (14)

Symmetry code: (i) .