(R)-N-(Biphenyl-4-yl)-tert-butane­sulfinamide

Binbin Zhang; Yan Wang; Xiaofei Sun; Wenguo Wang; Qingle Zeng

doi:10.1107/S1600536812015127

. 2012 Apr 13;68(Pt 5):o1389. doi: 10.1107/S1600536812015127

(R)-N-(Biphenyl-4-yl)-tert-butanesulfinamide

Binbin Zhang ^a, Yan Wang ^a, Xiaofei Sun ^a, Wenguo Wang ^b, Qingle Zeng ^a,^*

PMCID: PMC3344516 PMID: 22590278

Abstract

In the title compound, C₁₆H₁₉NOS, 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 molecules 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 _r = 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
Δρ_max = 0.19 e Å⁻³
Δρ_min = −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.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015127/rz2735sup1.cif

e-68-o1389-sup1.cif^{(17.8KB, cif)}

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

e-68-o1389-Isup2.hkl^{(135.8KB, 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

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

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Sci-Tech Bureau of Sichuan (No. 2011HH0016), the Opening Fund of the State Key Laboratory of Geohazard Prevention and Geoenvironment Protection (No. SKLGP2012K005) and the Cultivating Programme for the Excellent Innovation Team of Chengdu University of Technology (No. HY0084) for financial support.

supplementary crystallographic information

Comment

Sulfinamides, especially chiral sulfinamides, are an important class of organic compounds in modern organic chemistry, and a great number of such compounds have been synthesized. In our continuous study on chiral N-aryl-tert-butanesulfinamides (Sun et al., 2012), we have prepared the title compound and report its crystal structure herein.

In the molecule of the title compound (Fig. 1) the aromatic rings of the biphenyl are tilted to form a dihedral angle of 38.98 (8)°, which is comparable to the value observed in other related compounds containing the biphenyl group (Jasinski et al., 2012; Gainsford et al., 2011). In the crystal packing (Fig. 2), the molecules are linked by intermolecular N—H···O hydrogen bonds (Table 1) into one-dimensional chains running parallel to the the a axis.

Experimental

A oven-dried ground test tube, which was equipped with a magnetic stir bar and fitted with a rubber septum, was charged with (R)-tert-butanesulfinamide (0.121 g, 1.0 mmol), Pd2(dba)3 (0.018 g, 0.02 mmol; dba is dibenzylideneacetone), 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl (0.0212 g, 0.05 mmol) and NaOH (0.08 g, 2 mmol). The vessel was evacuated and backfilled with argon three times, then 4-biphenyl bromide (1.3 mmol), toluene (10 ml) and degassed water (0.3 ml) were added via syringe. The solution was stirred at 90°C for 20 h. The reaction mixture was then cooled to room temperature, quenched by water, and extracted with chloroform (20 ml) for twice. The organic layers were combined, and dried over anhydrous sodium sulfate and filtrated. The filterate was condensed under vacuum. The residual was purified with silica gel column chromatography with a solution of petroleum ether and ethyl acetate (5:1 v/v) as eluent to give the title compound (R)-N-(4-biphenyl)-tert-butanesulfinamide. A test tube containing a petroleum ether and ethyl acetate (1:1 v/v) solution of the title compound was covered with a piece of filter paper and placed motionless at room temperature, and a single-crystal was cultured in the bottom of the test tube. Spectroscopic analysis: ¹H NMR (300 MHz, CDCl₃), δ (ppm): 7.49–7.29 (m, 7H), 7.06 (d, J = 8.5 Hz, 2H), 6.03 (d, J = 3.9 Hz, 1H), 1.37 (s, 9H). ¹³C NMR (300 MHz, CDCl₃), δ (ppm): 114.6, 140.4, 135.6, 128.6, 127.9, 126.8, 126.6, 118.4, 56.5, 22.4. FT—IR (KBr) (cm^-1): 3453, 3252, 2926, 1610, 1519, 1485, 1386, 1305, 1286, 1268, 1228, 1191, 1057, 912, 880, 838, 767. [α]D = -110.8 (c 0.15, ethyl acetate). ESI-MS (negative mode), m/z = 272 [M—H]-. Anal. Calcd for C₁₆H₁₉NOS: C, 70.29; H, 7.00; N, 5.12. Found: C, 70.43; H, 7.16; N 5.01.