(R)-N-(3-Meth­oxy­phen­yl)-tert-butane­sulfinamide

Sun, X.; Dai, C.; Tu, X.; Wang, W.; Zeng, Q.

doi:10.1107/S1600536812006496

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o773

doi:10.1107/S1600536812006496

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(R)-N-(3-Methoxyphenyl)-tert-butanesulfinamide

Xiaofei Sun,^a Chuan Dai,^a Xingzhao Tu,^a Wenguo Wang ^b and Qingle Zeng ^a ^*

^aInstitute 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 9 February 2012; accepted 14 February 2012; online 17 February 2012)

The title compound, C₁₁H₁₇NO₂S, was obtained by the reaction of (R)-tert-butanesulfinamide with 3-methoxyphenyl bromide in toluene. In the crystal, molecules interact head-to-tail through N—H⋯O and C—H⋯O hydrogen bonds, forming one-dimensional chains parallel to the a axis.

Related literature

For the structure of the racemic title compound, see: Datta et al. (2010 ). For the structures of related N-arylalkanesulfinamides, see: Datta et al. (2008 , 2009a ,b ). For the structures of related N-alkylalkanesulfinamides, see: Sato et al. (1975 ); Schuckmann et al. (1978 ); Ferreira et al. (2005 ).

Experimental

Crystal data

C₁₁H₁₇NO₂S
M_r = 227.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.4418 (9) Å
b = 9.7027 (12) Å
c = 16.862 (2) Å
V = 1217.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.990, T_max = 1.0
7010 measured reflections
2481 independent reflections
2062 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.092
S = 1.10
2481 reflections
204 parameters
All H-atom parameters refined
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1029 Friedel pairs
Flack parameter: −0.02 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.80 (2)	2.28 (3)	3.031 (3)	157 (2)
C10—H10A⋯O2ⁱ	1.02 (3)	2.47 (3)	3.487 (4)	171 (2)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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/S1600536812006496/rz2711sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006496/rz2711Isup4.hkl

Supporting information file. DOI: 10.1107/S1600536812006496/rz2711Isup3.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 study on sulfinamides, we have prepared the title compound and report its crystal structure herein.

In the molecule of the title compound (Fig. 1), the N–C_aryl bond length [1.416 (3) Å] is quite similar to that found in the racemic 3-MeO-N-phenyl-tert-butanesulfinamide (1.418 (2) Å; Datta et al., 2010), and could be compared with those reported for 4-MeO-N-phenyl-tert-butanesulfinamide (1.4225 (14) Å; Datta et al., 2009a), N-phenyl-tert-butanesulfinamide (1.4083 (12) Å; Datta et al., 2009b) and other N-alkylalkanesulfinamides (1.470–1.530 Å; Sato et al., 1975; Schuckmann et al., 1978; Ferreira et al., 2005). The crystal packing shows an intermolecular interaction through N-H···O=S hydrogen bond, forming a chain structure parallel to the a axis (Fig. 2; Table 1). In addition, the chain is enforced by an intermolecular C-H···O=S hydrogen bond as observed in the crystal packing of N-phenyladamantane-1-sulfinamide (Datta et al., 2008).

Related literature top

For the structure of the racemic title compound, see: Datta et al. (2010). For the structures of related N-arylalkanesulfinamides, see: Datta et al. (2008, 2009a,b). For the structures of related N-alkylalkanesulfinamides, see: Sato et al. (1975); Schuckmann et al. (1978); Ferreira et al. (2005).

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 3-methoxyphenyl 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 ethyl acetate (20 mL) for twice. The organic layer was 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. A test tube containing the eluate 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. Yield: 0.186 g, 82%. Spectroscopic analysis: ESI-MS (negative mode), m/z = 226 [M-H]-. FTIR (KBr) (cm^-1): 3456, 3273, 3112, 3076, 2966, 1584, 1519, 1246, 1186, 1113, 1068, 875, 795, 751. ¹H NMR (300 MHz, CDCl₃), δ (ppm): 7.16 (t, J = 8.2 Hz, 1H), 5.60-5.55 (m, 3H), 5.34 (s, 1H), 3.78(s, 3H), 1.33 (s, 9H). ¹³C NMR (300 MHz, CD₃OD), δ (ppm): 160.2, 143.5, 129.8, 110.1, 107.9, 103.5, 56.3, 54.9, 22.3. [α]D = -2.6 (c 0.05, ethyl acetate).

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. The molecular structure of the title compound with 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The chain structure of the title compound formed by intermolecular N—H···O hydrogen bonds (dashed lines).

(R)-N-(3-Methoxyphenyl)-tert-butanesulfinamide top

Crystal data top

C₁₁H₁₇NO₂S	D_x = 1.246 Mg m⁻³
M_r = 227.33	Melting point: 375 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2411 reflections
a = 7.4418 (9) Å	θ = 3.0–29.1°
b = 9.7027 (12) Å	µ = 0.25 mm⁻¹
c = 16.862 (2) Å	T = 293 K
V = 1217.5 (3) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm
F(000) = 488

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2481 independent reflections
Radiation source: fine-focus sealed tube	2062 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 3.0°
ω scans	h = −9→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→12
T_min = 0.990, T_max = 1.0	l = −18→21
7010 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)] = 0.043	All H-atom parameters refined
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0403P)²] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
2481 reflections	Δρ_max = 0.22 e Å⁻³
204 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1029 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (9)

Crystal data top

C₁₁H₁₇NO₂S	V = 1217.5 (3) Å³
M_r = 227.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.4418 (9) Å	µ = 0.25 mm⁻¹
b = 9.7027 (12) Å	T = 293 K
c = 16.862 (2) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2481 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2062 reflections with I > 2σ(I)
T_min = 0.990, T_max = 1.0	R_int = 0.031
7010 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	All H-atom parameters refined
wR(F²) = 0.092	Δρ_max = 0.22 e Å⁻³
S = 1.10	Δρ_min = −0.29 e Å⁻³
2481 reflections	Absolute structure: Flack (1983), 1029 Friedel pairs
204 parameters	Absolute structure parameter: −0.02 (9)
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	−0.84124 (9)	−0.41552 (6)	−0.07783 (3)	0.04091 (18)
O1	−0.6725 (4)	0.18196 (19)	−0.18439 (11)	0.0691 (6)
O2	−1.0171 (2)	−0.39294 (19)	−0.03812 (10)	0.0543 (5)
N1	−0.7259 (3)	−0.2699 (2)	−0.08452 (13)	0.0464 (5)
C1	−0.7230 (3)	0.0498 (3)	−0.20153 (15)	0.0468 (7)
C2	−0.7075 (3)	−0.0421 (3)	−0.13905 (15)	0.0416 (6)
C3	−0.7532 (3)	−0.1789 (3)	−0.14907 (14)	0.0390 (6)
C4	−0.8154 (4)	−0.2233 (3)	−0.22198 (15)	0.0540 (7)
C5	−0.8331 (5)	−0.1298 (3)	−0.28284 (17)	0.0627 (8)
C6	−0.7857 (4)	0.0065 (3)	−0.27436 (17)	0.0561 (8)
C7	−0.6704 (6)	0.2798 (4)	−0.2476 (2)	0.0730 (10)
C8	−0.6971 (3)	−0.5045 (3)	−0.00507 (14)	0.0423 (6)
C9	−0.5083 (4)	−0.5131 (4)	−0.0392 (2)	0.0621 (8)
C10	−0.7023 (5)	−0.4311 (3)	0.07445 (17)	0.0527 (7)
C11	−0.7817 (6)	−0.6475 (3)	0.0011 (2)	0.0618 (9)
H9C	−0.509 (4)	−0.550 (3)	−0.0879 (18)	0.060 (9)*
H2	−0.667 (3)	−0.012 (2)	−0.0913 (14)	0.041 (6)*
H10A	−0.641 (4)	−0.337 (3)	0.0697 (16)	0.074 (9)*
H7B	−0.593 (4)	0.247 (3)	−0.2904 (19)	0.071 (10)*
H9B	−0.438 (5)	−0.567 (4)	−0.005 (2)	0.113 (14)*
H9A	−0.439 (4)	−0.423 (3)	−0.0417 (16)	0.065 (9)*
H5	−0.878 (4)	−0.161 (3)	−0.3324 (17)	0.060 (8)*
H6	−0.807 (4)	0.066 (3)	−0.3158 (15)	0.056 (8)*
H1	−0.692 (4)	−0.237 (2)	−0.0438 (14)	0.039 (7)*
H4	−0.845 (4)	−0.312 (3)	−0.2268 (15)	0.056 (8)*
H11C	−0.913 (5)	−0.641 (3)	0.0169 (18)	0.069 (10)*
H10C	−0.819 (4)	−0.425 (3)	0.0947 (17)	0.077 (10)*
H11A	−0.709 (4)	−0.705 (3)	0.0376 (17)	0.071 (9)*
H10B	−0.643 (4)	−0.481 (3)	0.1119 (16)	0.061 (8)*
H7A	−0.620 (5)	0.361 (4)	−0.224 (2)	0.103 (14)*
H7C	−0.793 (5)	0.285 (4)	−0.2714 (18)	0.095 (13)*
H11B	−0.775 (4)	−0.695 (3)	−0.0537 (18)	0.075 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0392 (3)	0.0430 (3)	0.0405 (3)	−0.0007 (3)	−0.0001 (3)	−0.0027 (3)
O1	0.0977 (18)	0.0545 (11)	0.0550 (11)	−0.0043 (13)	−0.0024 (13)	0.0189 (9)
O2	0.0394 (10)	0.0641 (12)	0.0594 (12)	0.0039 (10)	0.0060 (9)	0.0031 (9)
N1	0.0555 (14)	0.0464 (12)	0.0374 (12)	−0.0082 (10)	−0.0103 (12)	0.0041 (10)
C1	0.0424 (16)	0.0568 (16)	0.0414 (13)	0.0049 (12)	0.0027 (13)	0.0091 (11)
C2	0.0401 (15)	0.0520 (15)	0.0326 (13)	0.0047 (11)	0.0005 (12)	0.0048 (11)
C3	0.0304 (14)	0.0538 (14)	0.0328 (12)	0.0025 (11)	0.0020 (12)	0.0059 (10)
C4	0.061 (2)	0.0594 (17)	0.0419 (15)	−0.0038 (16)	−0.0022 (14)	−0.0001 (13)
C5	0.067 (2)	0.088 (2)	0.0333 (14)	−0.0040 (19)	−0.0088 (17)	−0.0004 (13)
C6	0.0509 (18)	0.076 (2)	0.0412 (15)	0.0086 (16)	0.0015 (14)	0.0183 (14)
C7	0.075 (3)	0.075 (2)	0.068 (2)	−0.007 (2)	0.004 (2)	0.0300 (18)
C8	0.0428 (15)	0.0392 (12)	0.0448 (14)	0.0019 (12)	−0.0018 (12)	0.0021 (10)
C9	0.0529 (19)	0.065 (2)	0.068 (2)	0.0114 (18)	0.0010 (19)	−0.0014 (18)
C10	0.0557 (19)	0.0586 (17)	0.0439 (14)	−0.0086 (15)	−0.0047 (16)	0.0064 (14)
C11	0.072 (3)	0.0414 (16)	0.072 (2)	−0.0058 (15)	−0.007 (2)	0.0048 (15)

Geometric parameters (Å, º) top

S1—O2	1.4866 (18)	C6—H6	0.92 (3)
S1—N1	1.657 (2)	C7—H7B	0.98 (3)
S1—C8	1.844 (2)	C7—H7A	0.96 (4)
O1—C1	1.367 (3)	C7—H7C	1.00 (4)
O1—C7	1.428 (3)	C8—C9	1.521 (4)
N1—C3	1.416 (3)	C8—C10	1.519 (4)
N1—H1	0.80 (2)	C8—C11	1.527 (4)
C1—C2	1.385 (3)	C9—H9C	0.90 (3)
C1—C6	1.379 (4)	C9—H9B	0.93 (4)
C2—C3	1.381 (3)	C9—H9A	1.01 (3)
C2—H2	0.91 (2)	C10—H10A	1.02 (3)
C3—C4	1.382 (4)	C10—H10C	0.94 (3)
C4—C5	1.376 (4)	C10—H10B	0.91 (3)
C4—H4	0.90 (3)	C11—H11C	1.02 (3)
C5—C6	1.376 (4)	C11—H11A	0.99 (3)
C5—H5	0.95 (3)	C11—H11B	1.03 (3)

S1—N1—H1	116.3 (18)	C8—C9—H9C	111.4 (19)
O1—C1—C2	114.8 (2)	C8—C9—H9B	109 (2)
O1—C1—C6	124.5 (2)	C8—C9—H9A	115.9 (17)
O1—C7—H7B	109.7 (18)	C8—C10—H10A	109.8 (16)
O1—C7—H7A	104 (2)	C8—C10—H10C	112.1 (19)
O1—C7—H7C	109 (2)	C8—C10—H10B	110.3 (17)
O2—S1—N1	111.17 (12)	C8—C11—H11C	110.9 (17)
O2—S1—C8	106.35 (11)	C8—C11—H11A	109.0 (18)
N1—S1—C8	98.23 (12)	C8—C11—H11B	108.7 (17)
C1—O1—C7	118.0 (3)	C9—C8—S1	108.1 (2)
C1—C2—H2	119.6 (15)	C9—C8—C11	110.9 (3)
C1—C6—H6	122.8 (16)	C10—C8—S1	110.65 (19)
C2—C3—N1	118.0 (2)	C10—C8—C9	112.5 (3)
C2—C3—C4	119.4 (2)	C10—C8—C11	110.8 (2)
C3—N1—S1	120.62 (19)	C11—C8—S1	103.4 (2)
C3—N1—H1	117.4 (17)	H9C—C9—H9B	110 (3)
C3—C2—C1	120.3 (2)	H9C—C9—H9A	108 (3)
C3—C2—H2	120.1 (15)	H10A—C10—H10C	113 (3)
C3—C4—H4	117.5 (17)	H10A—C10—H10B	108 (2)
C4—C3—N1	122.5 (2)	H7B—C7—H7A	110 (3)
C4—C5—C6	122.1 (3)	H7B—C7—H7C	105 (3)
C4—C5—H5	118.5 (17)	H9B—C9—H9A	103 (3)
C5—C4—C3	119.4 (3)	H11C—C11—H11A	114 (3)
C5—C4—H4	123.1 (17)	H11C—C11—H11B	108 (3)
C5—C6—C1	118.2 (3)	H10C—C10—H10B	103 (2)
C5—C6—H6	118.8 (16)	H11A—C11—H11B	106 (2)
C6—C1—C2	120.6 (3)	H7A—C7—H7C	119 (3)
C6—C5—H5	119.4 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.80 (2)	2.28 (3)	3.031 (3)	157 (2)
C10—H10A···O2ⁱ	1.02 (3)	2.47 (3)	3.487 (4)	171 (2)

Symmetry code: (i) x+1/2, −y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇NO₂S
M_r	227.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	7.4418 (9), 9.7027 (12), 16.862 (2)
V (Å³)	1217.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.990, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	7010, 2481, 2062
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.092, 1.10
No. of reflections	2481
No. of parameters	204
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.29
Absolute structure	Flack (1983), 1029 Friedel pairs
Absolute structure parameter	−0.02 (9)

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···O2ⁱ	0.80 (2)	2.28 (3)	3.031 (3)	157 (2)
C10—H10A···O2ⁱ	1.02 (3)	2.47 (3)	3.487 (4)	171 (2)

Symmetry code: (i) x+1/2, −y−1/2, −z.

Acknowledgements

The authors thank the National Science Foundation of China (grant No. 20672088), the Ministry of Human Resources and Social Security of China, the Science and Technology Bureau of Sichuan (grant No. 2011HH0016), the Opening Fund of the State Key Laboratory of Geohazard Prevention and Geoenvironment Protection, and the Cultivating Programme for Excellent Innovation Team of Chengdu University of Technology (grant No. HY0084) for financial support.

References

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