(R)-N-[(R)-2,2-Di­chloro-1-phenyl-2-(phenyl­sulfon­yl)eth­yl]-2-methyl­propane-2-sulfinamide

Huang, H.; Li, Y.; Chu, J.

doi:10.1107/S1600536813034909

organic compounds

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ISSN: 2056-9890

Volume 70| Part 2| February 2014| Page o119

doi:10.1107/S1600536813034909

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(R)-N-[(R)-2,2-Dichloro-1-phenyl-2-(phenylsulfonyl)ethyl]-2-methylpropane-2-sulfinamide

Haiji Huang,^a Ya Li ^a ^* and Jingming Chu ^a

^aCollege of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, People's Republic of China
^*Correspondence e-mail: ya.li@sues.edu.cn

(Received 9 December 2013; accepted 30 December 2013; online 8 January 2014)

The title molecule, C₁₈H₂₁Cl₂NO₃S₂, contains one chiral carbon center and the absolute sterochemistry has been confirmed as as R. An intramolecular N—H⋯O hydrogen bond occurs and the dihedral angle between the benzene rings is 64.5 (1)°. In the crystal, the molecules are linked by weak C—H⋯O hydrogen bonds, forming a zigzag chain structure extending along the c-axis direction.

CCDC reference: 979063

Related literature

For the use of β-amino sulfones as enzyme inhibitors, see: Tamamura et al. (2003 ); Nakatani et al. (2008 ); Raja et al. (2009 ). For their use as synthetic intermediates, see: Pauly et al. (1994 ); de Blas et al. (1994 ); Carretero et al. (1997 ); Alonso et al. (1997 ). For their synthesis, see: Zhang et al. (2011 ). For the fluorinated analogue, see: Li & Hu (2005 ); Liu & Hu (2010 ).

Experimental

Crystal data

C₁₈H₂₁Cl₂NO₃S₂
M_r = 434.38
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.924 (2) Å
b = 14.772 (4) Å
c = 18.151 (5) Å
V = 2124.6 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 293 K
0.39 × 0.30 × 0.26 mm

Data collection

Bruker CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.743, T_max = 1.000
11625 measured reflections
4174 independent reflections
3834 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.086
S = 0.99
4174 reflections
242 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack, 1983 : 1786 Friedel pairs
Absolute structure parameter: −0.04 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O1ⁱ	0.93	2.44	3.236 (4)	144
N1—H1⋯O2	0.81 (3)	2.19 (3)	2.889 (3)	145 (3)
Symmetry code: (i) $[-x-{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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.

Supporting information

CCDC reference: 979063

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813034909/zs2283sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813034909/zs2283Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813034909/zs2283Isup3.cml

checkCIF report

Comment top

The β-amino sulfone motif is of significant importance because it was found to play important roles in a variety of bioactive compounds (Tamamura et al., 2003; Nakatani et al., 2008). Besides, β-amino sulfones are valuable intermediates in the preparation of a wide variety of interesting compounds (Pauly et al., 1994; Zhang et al., 2011). Herein, we report the crystal structure of a α,α-dichloro-β-amino sulfone, the title compound, C₁₈H₂₁Cl₂NO₃S₂, which may find potential use in the synthesis of bioactive compounds.

In this compound (Fig. 1), the benzene rings A (C3–C8) and B (C13-C18) are planar with r. m. s. deviations of 0.0053 Å and 0.0050 Å, respectively. The dihedral angle between A and B is 64.5 (1)°. An intramolecular N1—H···O2 hydrogen-bonding interaction is present while a weak intermolecular C17—H···O1ⁱ hydrogen bond (Table 1, Figs. 2,3) results in a one-dimensional zigzag chain structure extending along c. Present also are 40 Å³ solvent accessible voids. The absolute configuration at the chiral centre [C2(R)] has been confirmed [absolute structure parameter = -0.04 (6) for 1786 Friedel pairs] (Flack, 1983).

Related literature top

For the use of β-amino sulfones as enzyme inhibitors, see: Tamamura et al. (2003); Nakatani et al. (2008); Raja et al. (2009). For their use as synthetic intermediates, see: Pauly et al. (1994); de Blas et al. (1994); Carretero et al. (1997); Alonso et al. (1997). For their synthesis, see: Zhang et al. (2011). For the fluorinated analogue, see: Li & Hu (2005); Liu & Hu (2010).

Experimental top

Sodium bis(trimethylsilyl)amide (1.2 mmol, 1M in THF) was added slowly to a reaction mixture of (Rs)-N-benzylidene-2-methylpropane-2-sulfinamide (209 mg, 1.0 mmol) and (dichloromethylsulfonyl)benzene (225 mg, 1.0 mmol) in THF at 203 K. The mixture was stirred for 1 h at this temperature and then quenched with 1M HCl. The quenched mixture was extracted with EtOAc. After removal of the solvent, the residue was subjected to flash colume chromatography to give the title compound (226 mg: yield, 52%). The obtained compound was recrystallized from ethyl acetate/hexane (1:1) to give colorless crystals.

Structure description top

For the use of β-amino sulfones as enzyme inhibitors, see: Tamamura et al. (2003); Nakatani et al. (2008); Raja et al. (2009). For their use as synthetic intermediates, see: Pauly et al. (1994); de Blas et al. (1994); Carretero et al. (1997); Alonso et al. (1997). For their synthesis, see: Zhang et al. (2011). For the fluorinated analogue, see: Li & Hu (2005); Liu & Hu (2010).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. Intramolecular N—H···O and intermolecular C—H···O interactions in the title compound, shown as dashed lines. For symmetry code a: -x - 1/2, -y, z - 1/2.
	Fig. 3. The zigzag chain formed via intermolecular C—H···O interactions, viewed along the b axis. The intramolecular hydrogen bonds are omitted for clarity.

(R)-N-[(R)-2,2-Dichloro-1-phenyl-2-(phenylsulfonyl)ethyl]-2-methylpropane-2-sulfinamide top

Crystal data top

C₁₈H₂₁Cl₂NO₃S₂	F(000) = 904
M_r = 434.38	D_x = 1.358 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4807 reflections
a = 7.924 (2) Å	θ = 5.3–51.2°
b = 14.772 (4) Å	µ = 0.52 mm⁻¹
c = 18.151 (5) Å	T = 293 K
V = 2124.6 (10) Å³	Prismatic, colorless
Z = 4	0.39 × 0.30 × 0.26 mm

Data collection top

Bruker CCD area-detector diffractometer	4174 independent reflections
Radiation source: fine-focus sealed tube	3834 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
φ and ω scans	θ_max = 26.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
T_min = 0.743, T_max = 1.000	k = −18→12
11625 measured reflections	l = −22→22

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0379P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max < 0.001
4174 reflections	Δρ_max = 0.28 e Å⁻³
242 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Absolute structure: Flack, 1983: 1786 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (6)

Crystal data top

C₁₈H₂₁Cl₂NO₃S₂	V = 2124.6 (10) Å³
M_r = 434.38	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.924 (2) Å	µ = 0.52 mm⁻¹
b = 14.772 (4) Å	T = 293 K
c = 18.151 (5) Å	0.39 × 0.30 × 0.26 mm

Data collection top

Bruker CCD area-detector diffractometer	4174 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3834 reflections with I > 2σ(I)
T_min = 0.743, T_max = 1.000	R_int = 0.075
11625 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.086	Δρ_max = 0.28 e Å⁻³
S = 0.99	Δρ_min = −0.20 e Å⁻³
4174 reflections	Absolute structure: Flack, 1983: 1786 Friedel pairs
242 parameters	Absolute structure parameter: −0.04 (6)
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	0.31897 (9)	0.05580 (5)	0.41327 (3)	0.04581 (18)
S2	−0.02571 (8)	0.04757 (4)	0.21496 (3)	0.03700 (15)
Cl1	0.30446 (8)	−0.00843 (5)	0.15767 (3)	0.04829 (18)
Cl2	0.05808 (9)	−0.14312 (4)	0.19785 (4)	0.05009 (18)
N1	0.2849 (3)	0.04579 (15)	0.32217 (10)	0.0382 (5)
O1	0.1580 (3)	0.0660 (2)	0.45195 (11)	0.0862 (8)
O2	0.0522 (2)	0.13428 (12)	0.22302 (11)	0.0505 (5)
O3	−0.1488 (2)	0.01835 (13)	0.26710 (9)	0.0501 (5)
C1	0.1468 (3)	−0.03735 (16)	0.22190 (13)	0.0356 (5)
C2	0.2123 (3)	−0.04217 (15)	0.30187 (12)	0.0350 (5)
H2	0.1156	−0.0537	0.3342	0.042*
C3	0.3408 (3)	−0.11663 (16)	0.31436 (12)	0.0350 (5)
C4	0.5097 (3)	−0.10324 (17)	0.29887 (13)	0.0392 (6)
H4	0.5458	−0.0477	0.2805	0.047*
C5	0.6241 (4)	−0.17113 (19)	0.31038 (14)	0.0481 (7)
H5	0.7373	−0.1616	0.2993	0.058*
C6	0.5737 (4)	−0.2531 (2)	0.33810 (17)	0.0584 (8)
H6	0.6522	−0.2990	0.3456	0.070*
C7	0.4087 (5)	−0.2670 (2)	0.3544 (2)	0.0658 (9)
H7	0.3742	−0.3225	0.3732	0.079*
C8	0.2916 (4)	−0.19900 (19)	0.34330 (16)	0.0534 (7)
H8	0.1790	−0.2088	0.3554	0.064*
C9	0.4166 (4)	0.16808 (18)	0.41012 (14)	0.0459 (7)
C10	0.5815 (4)	0.1612 (2)	0.3691 (2)	0.0754 (10)
H10A	0.5600	0.1451	0.3188	0.113*
H10B	0.6509	0.1157	0.3916	0.113*
H10C	0.6386	0.2185	0.3708	0.113*
C11	0.4464 (5)	0.1909 (2)	0.49142 (18)	0.0764 (10)
H11A	0.5033	0.2481	0.4951	0.115*
H11B	0.5146	0.1446	0.5136	0.115*
H11C	0.3399	0.1943	0.5165	0.115*
C12	0.2961 (5)	0.2359 (2)	0.37614 (17)	0.0702 (10)
H12A	0.3346	0.2962	0.3865	0.105*
H12B	0.1855	0.2276	0.3966	0.105*
H12C	0.2920	0.2270	0.3238	0.105*
C13	−0.1098 (3)	0.04079 (18)	0.12566 (13)	0.0391 (6)
C14	−0.0407 (4)	0.0949 (2)	0.07116 (15)	0.0514 (7)
H14	0.0539	0.1305	0.0803	0.062*
C15	−0.1168 (4)	0.0943 (3)	0.00274 (17)	0.0673 (9)
H15	−0.0724	0.1292	−0.0352	0.081*
C16	−0.2563 (4)	0.0429 (2)	−0.00949 (16)	0.0656 (9)
H16	−0.3057	0.0432	−0.0560	0.079*
C17	−0.3265 (4)	−0.0098 (2)	0.04547 (17)	0.0581 (8)
H17	−0.4227	−0.0441	0.0364	0.070*
C18	−0.2513 (3)	−0.01063 (19)	0.11397 (15)	0.0463 (6)
H18	−0.2961	−0.0456	0.1518	0.056*
H1	0.237 (3)	0.0892 (18)	0.3050 (14)	0.041 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0602 (4)	0.0465 (4)	0.0308 (3)	−0.0052 (3)	−0.0030 (3)	0.0027 (3)
S2	0.0334 (3)	0.0386 (3)	0.0389 (3)	0.0012 (3)	−0.0006 (2)	−0.0038 (3)
Cl1	0.0409 (3)	0.0641 (4)	0.0399 (3)	0.0035 (3)	0.0099 (3)	0.0063 (3)
Cl2	0.0535 (4)	0.0381 (3)	0.0587 (4)	−0.0048 (3)	−0.0079 (3)	−0.0113 (3)
N1	0.0503 (13)	0.0327 (11)	0.0316 (10)	0.0010 (11)	−0.0046 (9)	0.0017 (9)
O1	0.0792 (15)	0.126 (2)	0.0538 (12)	−0.0324 (16)	0.0265 (12)	−0.0116 (13)
O2	0.0522 (11)	0.0372 (10)	0.0621 (12)	−0.0006 (9)	−0.0135 (10)	−0.0033 (8)
O3	0.0396 (9)	0.0694 (13)	0.0412 (9)	0.0064 (9)	0.0068 (8)	−0.0025 (9)
C1	0.0339 (12)	0.0355 (13)	0.0375 (12)	−0.0035 (10)	0.0007 (10)	−0.0024 (10)
C2	0.0373 (12)	0.0343 (12)	0.0334 (11)	−0.0039 (11)	0.0056 (10)	0.0023 (10)
C3	0.0373 (13)	0.0325 (13)	0.0352 (12)	−0.0022 (10)	−0.0024 (10)	−0.0008 (10)
C4	0.0414 (14)	0.0402 (14)	0.0360 (13)	0.0010 (11)	0.0054 (11)	0.0002 (11)
C5	0.0435 (15)	0.0576 (18)	0.0433 (14)	0.0084 (13)	0.0014 (12)	−0.0091 (13)
C6	0.063 (2)	0.0442 (17)	0.0677 (19)	0.0158 (15)	−0.0101 (16)	−0.0060 (15)
C7	0.073 (2)	0.0365 (16)	0.088 (2)	−0.0026 (15)	−0.0091 (19)	0.0145 (15)
C8	0.0458 (16)	0.0450 (16)	0.0693 (18)	−0.0078 (14)	−0.0022 (15)	0.0114 (14)
C9	0.0569 (17)	0.0404 (15)	0.0403 (14)	0.0007 (13)	−0.0041 (12)	−0.0078 (11)
C10	0.064 (2)	0.077 (2)	0.085 (2)	−0.024 (2)	0.0075 (18)	−0.0120 (19)
C11	0.103 (3)	0.071 (2)	0.0547 (18)	0.001 (2)	−0.025 (2)	−0.0192 (17)
C12	0.112 (3)	0.0453 (17)	0.0533 (17)	0.0220 (19)	−0.0169 (19)	−0.0043 (14)
C13	0.0370 (13)	0.0429 (14)	0.0373 (12)	0.0088 (12)	−0.0010 (10)	−0.0008 (11)
C14	0.0466 (15)	0.0557 (17)	0.0520 (17)	0.0031 (15)	0.0024 (13)	0.0057 (13)
C15	0.071 (2)	0.087 (2)	0.0443 (17)	0.017 (2)	0.0021 (16)	0.0115 (16)
C16	0.073 (2)	0.080 (2)	0.0440 (15)	0.022 (2)	−0.0168 (15)	−0.0116 (17)
C17	0.0516 (16)	0.0634 (19)	0.0594 (17)	0.0085 (16)	−0.0146 (15)	−0.0173 (15)
C18	0.0428 (14)	0.0472 (15)	0.0489 (15)	0.0021 (13)	−0.0045 (12)	−0.0064 (12)

Geometric parameters (Å, º) top

S1—O1	1.464 (2)	C8—H8	0.9300
S1—N1	1.682 (2)	C9—C10	1.507 (4)
S1—C9	1.831 (3)	C9—C12	1.516 (4)
S2—O3	1.4258 (18)	C9—C11	1.532 (4)
S2—O2	1.4296 (19)	C10—H10A	0.9600
S2—C13	1.755 (2)	C10—H10B	0.9600
S2—C1	1.860 (3)	C10—H10C	0.9600
Cl1—C1	1.761 (2)	C11—H11A	0.9600
Cl2—C1	1.768 (2)	C11—H11B	0.9600
N1—C2	1.468 (3)	C11—H11C	0.9600
N1—H1	0.81 (3)	C12—H12A	0.9600
C1—C2	1.543 (3)	C12—H12B	0.9600
C2—C3	1.516 (3)	C12—H12C	0.9600
C2—H2	0.9800	C13—C18	1.371 (4)
C3—C8	1.381 (4)	C13—C14	1.385 (4)
C3—C4	1.382 (3)	C14—C15	1.381 (4)
C4—C5	1.368 (4)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.359 (5)
C5—C6	1.371 (4)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.382 (5)
C6—C7	1.356 (5)	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.379 (4)
C7—C8	1.382 (4)	C17—H17	0.9300
C7—H7	0.9300	C18—H18	0.9300

O1—S1—N1	109.91 (13)	C10—C9—C12	112.9 (3)
O1—S1—C9	106.88 (15)	C10—C9—C11	110.9 (3)
N1—S1—C9	96.71 (11)	C12—C9—C11	110.1 (3)
O3—S2—O2	119.92 (12)	C10—C9—S1	108.7 (2)
O3—S2—C13	109.64 (12)	C12—C9—S1	110.2 (2)
O2—S2—C13	108.03 (12)	C11—C9—S1	103.6 (2)
O3—S2—C1	104.70 (11)	C9—C10—H10A	109.5
O2—S2—C1	106.24 (11)	C9—C10—H10B	109.5
C13—S2—C1	107.65 (11)	H10A—C10—H10B	109.5
C2—N1—S1	112.80 (16)	C9—C10—H10C	109.5
C2—N1—H1	115.1 (19)	H10A—C10—H10C	109.5
S1—N1—H1	112.7 (19)	H10B—C10—H10C	109.5
C2—C1—Cl1	113.30 (16)	C9—C11—H11A	109.5
C2—C1—Cl2	108.97 (16)	C9—C11—H11B	109.5
Cl1—C1—Cl2	109.45 (13)	H11A—C11—H11B	109.5
C2—C1—S2	110.00 (16)	C9—C11—H11C	109.5
Cl1—C1—S2	108.24 (12)	H11A—C11—H11C	109.5
Cl2—C1—S2	106.66 (12)	H11B—C11—H11C	109.5
N1—C2—C3	110.0 (2)	C9—C12—H12A	109.5
N1—C2—C1	109.09 (18)	C9—C12—H12B	109.5
C3—C2—C1	113.58 (19)	H12A—C12—H12B	109.5
N1—C2—H2	108.0	C9—C12—H12C	109.5
C3—C2—H2	108.0	H12A—C12—H12C	109.5
C1—C2—H2	108.0	H12B—C12—H12C	109.5
C8—C3—C4	118.5 (2)	C18—C13—C14	122.2 (2)
C8—C3—C2	120.5 (2)	C18—C13—S2	119.0 (2)
C4—C3—C2	121.1 (2)	C14—C13—S2	118.5 (2)
C5—C4—C3	120.4 (2)	C15—C14—C13	117.7 (3)
C5—C4—H4	119.8	C15—C14—H14	121.1
C3—C4—H4	119.8	C13—C14—H14	121.1
C4—C5—C6	120.7 (3)	C16—C15—C14	120.4 (3)
C4—C5—H5	119.6	C16—C15—H15	119.8
C6—C5—H5	119.6	C14—C15—H15	119.8
C7—C6—C5	119.6 (3)	C15—C16—C17	121.6 (3)
C7—C6—H6	120.2	C15—C16—H16	119.2
C5—C6—H6	120.2	C17—C16—H16	119.2
C6—C7—C8	120.4 (3)	C18—C17—C16	118.8 (3)
C6—C7—H7	119.8	C18—C17—H17	120.6
C8—C7—H7	119.8	C16—C17—H17	120.6
C3—C8—C7	120.4 (3)	C13—C18—C17	119.2 (3)
C3—C8—H8	119.8	C13—C18—H18	120.4
C7—C8—H8	119.8	C17—C18—H18	120.4

O1—S1—N1—C2	−72.4 (2)	C4—C5—C6—C7	−0.2 (4)
C9—S1—N1—C2	176.92 (18)	C5—C6—C7—C8	0.0 (5)
O3—S2—C1—C2	−56.98 (18)	C4—C3—C8—C7	−1.8 (4)
O2—S2—C1—C2	70.87 (18)	C2—C3—C8—C7	179.8 (3)
C13—S2—C1—C2	−173.60 (16)	C6—C7—C8—C3	1.0 (5)
O3—S2—C1—Cl1	178.74 (12)	O1—S1—C9—C10	−178.7 (2)
O2—S2—C1—Cl1	−53.41 (15)	N1—S1—C9—C10	−65.5 (2)
C13—S2—C1—Cl1	62.12 (15)	O1—S1—C9—C12	−54.5 (2)
O3—S2—C1—Cl2	61.06 (14)	N1—S1—C9—C12	58.8 (2)
O2—S2—C1—Cl2	−171.09 (12)	O1—S1—C9—C11	63.3 (2)
C13—S2—C1—Cl2	−55.56 (15)	N1—S1—C9—C11	176.5 (2)
S1—N1—C2—C3	−68.1 (2)	O3—S2—C13—C18	−17.1 (2)
S1—N1—C2—C1	166.75 (16)	O2—S2—C13—C18	−149.4 (2)
Cl1—C1—C2—N1	58.3 (2)	C1—S2—C13—C18	96.3 (2)
Cl2—C1—C2—N1	−179.58 (16)	O3—S2—C13—C14	156.5 (2)
S2—C1—C2—N1	−63.0 (2)	O2—S2—C13—C14	24.2 (2)
Cl1—C1—C2—C3	−64.7 (2)	C1—S2—C13—C14	−90.2 (2)
Cl2—C1—C2—C3	57.4 (2)	C18—C13—C14—C15	−1.6 (4)
S2—C1—C2—C3	173.99 (16)	S2—C13—C14—C15	−174.9 (2)
N1—C2—C3—C8	140.1 (2)	C13—C14—C15—C16	0.9 (4)
C1—C2—C3—C8	−97.3 (3)	C14—C15—C16—C17	0.2 (5)
N1—C2—C3—C4	−38.3 (3)	C15—C16—C17—C18	−0.7 (5)
C1—C2—C3—C4	84.2 (3)	C14—C13—C18—C17	1.0 (4)
C8—C3—C4—C5	1.6 (4)	S2—C13—C18—C17	174.3 (2)
C2—C3—C4—C5	−179.9 (2)	C16—C17—C18—C13	0.1 (4)
C3—C4—C5—C6	−0.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1ⁱ	0.93	2.44	3.236 (4)	144
N1—H1···O2	0.81 (3)	2.19 (3)	2.889 (3)	145 (3)
N1—H1···S2	0.81 (3)	2.72 (3)	3.138 (2)	114 (2)

Symmetry code: (i) −x−1/2, −y, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1ⁱ	0.93	2.44	3.236 (4)	144.2
N1—H1···O2	0.81 (3)	2.19 (3)	2.889 (3)	145 (3)

Symmetry code: (i) −x−1/2, −y, z−1/2.

Acknowledgements

The Innovation Program of Shanghai Municipal Education Commission (12YZ155) and the Innovation Program of National University Students (201310856014) are gratefully acknowledged.

References

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Volume 70| Part 2| February 2014| Page o119

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(R)-N-[(R)-2,2-Di­chloro-1-phenyl-2-(phenyl­sulfon­yl)eth­yl]-2-methyl­propane-2-sulfinamide

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Experimental

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organic compounds

(R)-N-[(R)-2,2-Dichloro-1-phenyl-2-(phenylsulfonyl)ethyl]-2-methylpropane-2-sulfinamide