(R)-N-[(R)-2,2-Di-chloro-1-phenyl-2-(phenyl-sulfon-yl)eth-yl]-2-methyl-propane-2-sulfinamide.

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

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 = 434.38

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.086

S = 0.99

4174 reflections

242 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack, 1983 ▶: 1786 Friedel pairs

Absolute structure parameter: −0.04 (6)

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.

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

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

Click here for additional data file.

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

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H21Cl2NO3S2	F(000) = 904
Mr = 434.38	Dx = 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

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

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(Fo2) + (0.0379P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max < 0.001
4174 reflections	Δρmax = 0.28 e Å−3
242 parameters	Δρmin = −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)

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	0.31897 (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)*

	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)

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)

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)

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) .