(R)-N-(Biphenyl-4-yl)-tert-butane-sulfinamide.

In the title compound, C(16)H(19)NOS, the dihedral angle between the two aromatic rings is 38.98 (8)°. The crystal structure is stabilized by N-H⋯O hydrogen bonds, which link neighbouring mol-ecules into chains running parallel to the a axis.

Related literature

For related structures, see: Sun et al. (2012 ▶); Jasinski et al. (2012 ▶); Gainsford et al. (2011 ▶).

Experimental

Crystal data

C16H19NOS

M = 273.38

Orthorhombic,

a = 9.3588 (5) Å

b = 11.9452 (5) Å

c = 13.3136 (7) Å

V = 1488.36 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.43 × 0.41 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.988, T max = 1.000

3983 measured reflections

2766 independent reflections

2325 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.097

S = 1.06

2766 reflections

175 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: assigned from the known absolute structure of the (R)-tert-butanesulfinamide starting material; the Flack (1983 ▶) parameter is consistent with this assignment, 1017 Friedel pairs

Flack parameter: 0.03 (10)

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/S1600536812015127/rz2735sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015127/rz2735Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015127/rz2735Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812015127/rz2735Isup4.cml

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

C16H19NOS	Dx = 1.220 Mg m−3
Mr = 273.38	Melting point: 427 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1425 reflections
a = 9.3588 (5) Å	θ = 3.1–28.9°
b = 11.9452 (5) Å	µ = 0.21 mm−1
c = 13.3136 (7) Å	T = 293 K
V = 1488.36 (12) Å3	Block, colourless
Z = 4	0.43 × 0.41 × 0.40 mm
F(000) = 584

Oxford Diffraction Xcalibur Eos diffractometer	2766 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2325 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −11→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→14
Tmin = 0.988, Tmax = 1.000	l = −16→16
3983 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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0358P)2 + 0.0448P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2766 reflections	Δρmax = 0.19 e Å−3
175 parameters	Δρmin = −0.22 e Å−3
0 restraints	Absolute structure: assigned from the known absolute structure of the (R)-tert-butanesulfinamide starting material; the Flack (1983) parameter is consistent with this assignment, 1017 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (10)

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	−0.15256 (8)	−0.31264 (5)	−0.40407 (5)	0.04256 (19)
O1	−0.2124 (3)	−0.22979 (16)	−0.47627 (16)	0.0639 (7)
N1	−0.0065 (3)	−0.36901 (17)	−0.45167 (18)	0.0488 (7)
H1	0.0702	−0.3294	−0.4536	0.059*
C1	−0.0021 (3)	−0.4790 (2)	−0.48927 (19)	0.0355 (6)
C2	−0.1153 (3)	−0.5532 (2)	−0.4810 (2)	0.0415 (7)
H2	−0.1987	−0.5318	−0.4482	0.050*
C3	−0.1032 (3)	−0.6600 (2)	−0.5220 (2)	0.0400 (7)
H3	−0.1801	−0.7090	−0.5166	0.048*
C4	0.0197 (3)	−0.6959 (2)	−0.57082 (17)	0.0357 (6)
C5	0.1315 (3)	−0.6196 (2)	−0.5777 (2)	0.0395 (6)
H5	0.2149	−0.6404	−0.6107	0.047*
C6	0.1217 (3)	−0.5131 (2)	−0.5366 (2)	0.0423 (7)
H6	0.1990	−0.4644	−0.5410	0.051*
C7	0.0310 (3)	−0.8089 (2)	−0.61585 (18)	0.0377 (6)
C8	−0.0253 (3)	−0.9024 (2)	−0.5693 (2)	0.0476 (8)
H8	−0.0694	−0.8944	−0.5071	0.057*
C9	−0.0181 (4)	−1.0075 (2)	−0.6126 (2)	0.0558 (8)
H9	−0.0581	−1.0688	−0.5801	0.067*
C10	0.0480 (4)	−1.0208 (3)	−0.7031 (3)	0.0600 (9)
H10	0.0535	−1.0914	−0.7324	0.072*
C11	0.1060 (3)	−0.9301 (3)	−0.7507 (2)	0.0586 (9)
H11	0.1514	−0.9395	−0.8122	0.070*
C12	0.0980 (3)	−0.8240 (2)	−0.7081 (2)	0.0471 (7)
H12	0.1375	−0.7630	−0.7414	0.057*
C13	−0.0712 (3)	−0.2310 (2)	−0.3024 (2)	0.0461 (7)
C14	−0.1958 (4)	−0.1746 (3)	−0.2498 (2)	0.0769 (12)
H14A	−0.2385	−0.1207	−0.2941	0.115*
H14B	−0.1622	−0.1375	−0.1903	0.115*
H14C	−0.2656	−0.2299	−0.2316	0.115*
C15	−0.0002 (6)	−0.3136 (3)	−0.2314 (3)	0.0911 (14)
H15A	−0.0670	−0.3713	−0.2138	0.137*
H15B	0.0301	−0.2752	−0.1718	0.137*
H15C	0.0812	−0.3465	−0.2639	0.137*
C16	0.0316 (4)	−0.1448 (2)	−0.3427 (3)	0.0670 (10)
H16A	0.1088	−0.1818	−0.3767	0.100*
H16B	0.0690	−0.1013	−0.2880	0.100*
H16C	−0.0173	−0.0965	−0.3889	0.100*

	U11	U22	U33	U12	U13	U23
S1	0.0340 (4)	0.0355 (3)	0.0581 (4)	0.0019 (3)	−0.0013 (4)	−0.0073 (4)
O1	0.0696 (17)	0.0521 (12)	0.0701 (14)	0.0165 (12)	−0.0276 (13)	−0.0088 (11)
N1	0.0381 (15)	0.0330 (11)	0.0754 (16)	−0.0062 (11)	0.0102 (13)	−0.0137 (11)
C1	0.0374 (16)	0.0289 (13)	0.0403 (14)	0.0022 (12)	−0.0009 (13)	−0.0009 (11)
C2	0.0343 (16)	0.0364 (14)	0.0538 (16)	0.0000 (13)	0.0130 (14)	−0.0031 (13)
C3	0.0377 (16)	0.0319 (14)	0.0505 (16)	−0.0043 (12)	0.0086 (14)	−0.0013 (12)
C4	0.0386 (15)	0.0326 (12)	0.0360 (13)	0.0026 (13)	−0.0008 (12)	0.0012 (12)
C5	0.0306 (15)	0.0389 (13)	0.0488 (16)	0.0043 (12)	0.0058 (14)	−0.0017 (13)
C6	0.0363 (17)	0.0353 (14)	0.0552 (17)	−0.0038 (13)	0.0004 (14)	−0.0009 (13)
C7	0.0333 (14)	0.0373 (13)	0.0423 (14)	0.0061 (13)	−0.0057 (12)	−0.0024 (13)
C8	0.0546 (19)	0.0393 (14)	0.0488 (17)	−0.0007 (15)	0.0038 (16)	−0.0023 (13)
C9	0.063 (2)	0.0360 (14)	0.068 (2)	−0.0014 (16)	−0.0094 (19)	−0.0060 (15)
C10	0.054 (2)	0.0503 (18)	0.075 (2)	0.0092 (17)	−0.021 (2)	−0.0296 (18)
C11	0.046 (2)	0.073 (2)	0.0567 (19)	0.0086 (19)	−0.0018 (16)	−0.0280 (18)
C12	0.0446 (18)	0.0491 (16)	0.0477 (16)	0.0017 (15)	−0.0003 (15)	−0.0044 (15)
C13	0.0484 (19)	0.0452 (15)	0.0447 (16)	0.0038 (14)	−0.0030 (15)	−0.0074 (14)
C14	0.075 (3)	0.085 (3)	0.070 (2)	0.006 (2)	0.014 (2)	−0.030 (2)
C15	0.125 (4)	0.076 (2)	0.073 (2)	0.018 (3)	−0.036 (3)	−0.002 (2)
C16	0.065 (2)	0.0593 (19)	0.077 (2)	−0.0194 (18)	0.001 (2)	−0.0224 (18)

S1—O1	1.489 (2)	C9—H9	0.9300
S1—N1	1.650 (2)	C9—C10	1.364 (4)
S1—C13	1.833 (3)	C10—H10	0.9300
N1—H1	0.8600	C10—C11	1.367 (4)
N1—C1	1.407 (3)	C11—H11	0.9300
C1—C2	1.385 (3)	C11—C12	1.391 (4)
C1—C6	1.381 (4)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.519 (4)
C2—C3	1.393 (3)	C13—C15	1.519 (4)
C3—H3	0.9300	C13—C16	1.508 (4)
C3—C4	1.389 (4)	C14—H14A	0.9600
C4—C5	1.390 (4)	C14—H14B	0.9600
C4—C7	1.481 (3)	C14—H14C	0.9600
C5—H5	0.9300	C15—H15A	0.9600
C5—C6	1.388 (3)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C8	1.381 (4)	C16—H16A	0.9600
C7—C12	1.390 (4)	C16—H16B	0.9600
C8—H8	0.9300	C16—H16C	0.9600
C8—C9	1.383 (4)
O1—S1—N1	109.58 (13)	C9—C10—H10	120.1
O1—S1—C13	106.21 (12)	C9—C10—C11	119.8 (3)
N1—S1—C13	99.00 (13)	C11—C10—H10	120.1
S1—N1—H1	118.6	C10—C11—H11	119.6
C1—N1—S1	122.8 (2)	C10—C11—C12	120.8 (3)
C1—N1—H1	118.6	C12—C11—H11	119.6
C2—C1—N1	123.1 (3)	C7—C12—C11	120.2 (3)
C6—C1—N1	117.5 (2)	C7—C12—H12	119.9
C6—C1—C2	119.3 (2)	C11—C12—H12	119.9
C1—C2—H2	120.2	C14—C13—S1	105.0 (2)
C1—C2—C3	119.5 (3)	C14—C13—C15	109.7 (3)
C3—C2—H2	120.2	C15—C13—S1	107.2 (2)
C2—C3—H3	118.9	C16—C13—S1	111.5 (2)
C4—C3—C2	122.2 (3)	C16—C13—C14	110.6 (3)
C4—C3—H3	118.9	C16—C13—C15	112.6 (3)
C3—C4—C5	116.8 (2)	C13—C14—H14A	109.5
C3—C4—C7	122.0 (2)	C13—C14—H14B	109.5
C5—C4—C7	121.2 (2)	C13—C14—H14C	109.5
C4—C5—H5	119.1	H14A—C14—H14B	109.5
C6—C5—C4	121.7 (3)	H14A—C14—H14C	109.5
C6—C5—H5	119.1	H14B—C14—H14C	109.5
C1—C6—C5	120.4 (3)	C13—C15—H15A	109.5
C1—C6—H6	119.8	C13—C15—H15B	109.5
C5—C6—H6	119.8	C13—C15—H15C	109.5
C8—C7—C4	121.9 (2)	H15A—C15—H15B	109.5
C8—C7—C12	117.6 (2)	H15A—C15—H15C	109.5
C12—C7—C4	120.5 (2)	H15B—C15—H15C	109.5
C7—C8—H8	119.1	C13—C16—H16A	109.5
C7—C8—C9	121.9 (3)	C13—C16—H16B	109.5
C9—C8—H8	119.1	C13—C16—H16C	109.5
C8—C9—H9	120.1	H16A—C16—H16B	109.5
C10—C9—C8	119.8 (3)	H16A—C16—H16C	109.5
C10—C9—H9	120.1	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.35	3.144 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.35	3.144 (3)	154

Symmetry code: (i) .