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

Zhang, B.; Wang, Y.; Sun, X.; Wang, W.; Zeng, Q.

doi:10.1107/S1600536812015127

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1389

doi:10.1107/S1600536812015127

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

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

^aState Key Lab of Geohazard Prevention and Geoenvironment Protection and Institute of Green Catalysis and Synthesis, College of Materials and Chemistry and Chemical Engineering, Chengdu University of Technology, Chengdu 610059, People's Republic of China, and ^bFujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, People's Republic of China
^*Correspondence e-mail: qinglezeng@hotmail.com

(Received 30 March 2012; accepted 5 April 2012; online 13 April 2012)

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, P 2₁ 2₁ 2₁
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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.047
wR(F²) = 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)

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) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z-1]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812015127/rz2735sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812015127/rz2735Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812015127/rz2735Isup4.cml

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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 (Dolomanov et al., 2009).

Figures top

	Fig. 1. Molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The one-dimensional structure of (I) in the crystal packing, showing intermolecular hydrogen bonding as dashed lines.

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

Crystal data top

C₁₆H₁₉NOS	D_x = 1.220 Mg m⁻³
M_r = 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

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2766 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2325 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 3.1°
ω scans	h = −11→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→14
T_min = 0.988, T_max = 1.000	l = −16→16
3983 measured reflections

Refinement top

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(F_o²) + (0.0358P)² + 0.0448P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2766 reflections	Δρ_max = 0.19 e Å⁻³
175 parameters	Δρ_min = −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	Absolute structure parameter: 0.03 (10)

Crystal data top

C₁₆H₁₉NOS	V = 1488.36 (12) Å³
M_r = 273.38	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.3588 (5) Å	µ = 0.21 mm⁻¹
b = 11.9452 (5) Å	T = 293 K
c = 13.3136 (7) Å	0.43 × 0.41 × 0.40 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2766 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2325 reflections with I > 2σ(I)
T_min = 0.988, T_max = 1.000	R_int = 0.019
3983 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.097	Δρ_max = 0.19 e Å⁻³
S = 1.06	Δρ_min = −0.22 e Å⁻³
2766 reflections	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
175 parameters	Absolute structure parameter: 0.03 (10)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y−1/2, −z−1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉NOS
M_r	273.38
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.3588 (5), 11.9452 (5), 13.3136 (7)
V (Å³)	1488.36 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.43 × 0.41 × 0.40

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.988, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3983, 2766, 2325
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.097, 1.06
No. of reflections	2766
No. of parameters	175
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22
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
Absolute structure parameter	0.03 (10)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.35	3.144 (3)	154.3

Symmetry code: (i) x+1/2, −y−1/2, −z−1.

Acknowledgements

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.

References

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