(S,2S,3R)-2-(2-Methyl-propane-2-sulfin-amido)-3-phenyl-butyronitrile.

The absolute configuration has been determined for the title compound, C(14)H(20)N(2)OS. Inter-molecular N-H⋯O hydrogen bonds are observed in the crystal packing, forming infinitive one-dimensional chains with the base vector [100].

Related literature

For uses of tert-butane­sulfinimines, see: Ferreira et al. (2009 ▶). For asymmetric Strecker reactions utilizing this auxiliary, see: Davis et al. (1994 ▶); Li et al. (2003 ▶). For the mannopeptimycin gene cluster, see: Magarvey et al. (2006 ▶). For a related structure, see: Harms et al. (2009 ▶).

Experimental

Crystal data

C14H20N2OS

M = 264.38

Orthorhombic,

a = 8.7892 (3) Å

b = 8.7967 (4) Å

c = 18.5217 (7) Å

V = 1432.02 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.36 × 0.18 × 0.15 mm

Data collection

STOE IPDS II diffractometer

Absorption correction: none

22029 measured reflections

3031 independent reflections

2624 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.064

S = 0.92

3031 reflections

244 parameters

All H-atom parameters refined

Δρmax = 0.18 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1272 Friedel pairs

Flack parameter: 0.02 (6)

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SIR2004 (Burla et al, 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041233/pv2212sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041233/pv2212Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H20N2OS	F(000) = 568
Mr = 264.38	Dx = 1.226 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 22507 reflections
a = 8.7892 (3) Å	θ = 2.2–25°
b = 8.7967 (4) Å	µ = 0.22 mm−1
c = 18.5217 (7) Å	T = 100 K
V = 1432.02 (10) Å3	Prism, colourless
Z = 4	0.36 × 0.18 × 0.15 mm

STOE IPDS II diffractometer	2624 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.070
graphite	θmax = 26.8°, θmin = 2.2°
area detetor, ω scans	h = −11→11
22029 measured reflections	k = −11→11
3031 independent reflections	l = −23→23

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.0378P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.064	(Δ/σ)max < 0.001
S = 0.92	Δρmax = 0.18 e Å−3
3031 reflections	Δρmin = −0.23 e Å−3
244 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008)
0 restraints	Extinction coefficient: 0.0113 (13)
0 constraints	Absolute structure: Flack (1983), 1272 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.02 (6)

Experimental. δH(300 MHz; DMSO) 1.13 (s, 9H, tBu), 1.28 (d, 3H, 3JMe,CH = 7.0 Hz, CH3), 3.14 (dq, 1H, 3JCH,CHN = 9.9, JCH,Me = 7.0 Hz, CH), 4.48 (pt, 1H, 3JCHN,CH = 9.9 Hz, CHN), 6.37 (d, 1H, 3JNH,CHN = 9.9 Hz, NH), 7.22 – 7.38 (m, 5H, CHarom); δC(75 MHz; DMSO-d6) 18.3 (CH3), 22.5 (C(CH3)3), 43.6 (CH), 52.4 (CHN), 56.4 (C(CH3)3), 119.8 (CN), 127.2 (p-CHarom), 127.8 (CHarom),128.5 (CHarom), 141.7 (i-Carom).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.43208 (18)	0.5330 (2)	−0.00956 (9)	0.0303 (4)
C2	0.56755 (17)	0.6458 (2)	−0.00597 (9)	0.0311 (4)
C3	0.40206 (16)	0.4817 (2)	−0.08405 (11)	0.0337 (4)
C4	0.57924 (19)	0.7071 (2)	0.07072 (10)	0.0343 (4)
C5	0.55157 (17)	0.7666 (2)	−0.06356 (9)	0.0322 (4)
C6	0.46159 (19)	0.8950 (2)	−0.05357 (10)	0.0362 (4)
C7	0.4397 (2)	0.9986 (2)	−0.10900 (12)	0.0451 (5)
C8	0.5075 (2)	0.9750 (3)	−0.17589 (12)	0.0480 (5)
C9	0.5996 (2)	0.8499 (3)	−0.18570 (11)	0.0467 (5)
C10	0.6223 (2)	0.7472 (2)	−0.13039 (10)	0.0394 (4)
C11	0.39529 (17)	0.2377 (2)	0.15401 (9)	0.0321 (4)
C12	0.4864 (3)	0.3546 (3)	0.19584 (12)	0.0498 (5)
C13	0.2643 (2)	0.1791 (3)	0.20040 (12)	0.0447 (5)
C14	0.4918 (2)	0.1082 (3)	0.12683 (12)	0.0459 (5)
N1	0.45589 (15)	0.40435 (17)	0.03876 (8)	0.0302 (3)
N2	0.37703 (17)	0.4385 (2)	−0.14134 (9)	0.0449 (4)
O1	0.23286 (12)	0.20929 (14)	0.03335 (7)	0.0376 (3)
S1	0.30144 (4)	0.33362 (5)	0.07741 (2)	0.03041 (11)
H2	0.6626 (19)	0.578 (2)	−0.0175 (9)	0.034 (5)*
H4A	0.655 (2)	0.795 (2)	0.0753 (11)	0.042 (5)*
H8	0.495 (2)	1.053 (3)	−0.2164 (11)	0.059 (6)*
H01	0.521 (2)	0.334 (2)	0.0226 (10)	0.038 (5)*
H4B	0.486 (2)	0.751 (2)	0.0859 (10)	0.041 (5)*
H10	0.689 (2)	0.649 (2)	−0.1366 (10)	0.049 (5)*
H1	0.3383 (18)	0.586 (2)	0.0075 (9)	0.030 (4)*
H13A	0.307 (3)	0.113 (3)	0.2399 (12)	0.064 (7)*
H6	0.417 (2)	0.910 (2)	−0.0079 (10)	0.040 (5)*
H14C	0.570 (2)	0.146 (2)	0.0968 (11)	0.053 (6)*
H12A	0.509 (3)	0.315 (3)	0.2468 (13)	0.063 (6)*
H14B	0.425 (2)	0.024 (3)	0.0969 (13)	0.059 (7)*
H4C	0.604 (2)	0.621 (2)	0.1034 (11)	0.051 (6)*
H13B	0.205 (3)	0.270 (3)	0.2212 (12)	0.067 (7)*
H12C	0.576 (3)	0.393 (3)	0.1711 (14)	0.080 (8)*
H7	0.379 (2)	1.088 (3)	−0.0992 (12)	0.053 (6)*
H12B	0.424 (3)	0.447 (3)	0.2040 (12)	0.060 (7)*
H9	0.650 (2)	0.827 (3)	−0.2315 (12)	0.060 (6)*
H14A	0.539 (3)	0.049 (3)	0.1672 (12)	0.061 (7)*
H13C	0.192 (3)	0.115 (3)	0.1726 (12)	0.061 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0237 (8)	0.0324 (9)	0.0348 (9)	0.0004 (7)	−0.0002 (7)	−0.0003 (7)
C2	0.0230 (7)	0.0334 (10)	0.0368 (9)	−0.0003 (7)	0.0000 (6)	0.0008 (8)
C3	0.0232 (7)	0.0387 (9)	0.0394 (10)	−0.0018 (6)	0.0012 (7)	−0.0008 (9)
C4	0.0303 (8)	0.0346 (10)	0.0381 (10)	−0.0040 (7)	−0.0005 (7)	−0.0012 (8)
C5	0.0242 (7)	0.0346 (9)	0.0378 (9)	−0.0056 (7)	−0.0021 (6)	−0.0003 (8)
C6	0.0240 (8)	0.0381 (10)	0.0465 (10)	−0.0054 (7)	−0.0032 (7)	0.0046 (8)
C7	0.0304 (9)	0.0389 (11)	0.0661 (14)	−0.0059 (8)	−0.0134 (9)	0.0087 (10)
C8	0.0445 (10)	0.0477 (13)	0.0518 (12)	−0.0203 (9)	−0.0177 (9)	0.0157 (10)
C9	0.0468 (10)	0.0524 (13)	0.0408 (11)	−0.0187 (10)	−0.0043 (8)	0.0025 (11)
C10	0.0368 (9)	0.0407 (11)	0.0408 (10)	−0.0094 (8)	0.0004 (7)	0.0008 (9)
C11	0.0264 (8)	0.0318 (9)	0.0380 (9)	−0.0014 (7)	0.0002 (6)	−0.0011 (8)
C12	0.0603 (12)	0.0454 (13)	0.0436 (11)	−0.0135 (11)	−0.0102 (10)	0.0023 (11)
C13	0.0351 (9)	0.0486 (12)	0.0505 (11)	0.0009 (10)	0.0047 (8)	0.0134 (11)
C14	0.0428 (10)	0.0481 (12)	0.0466 (11)	0.0145 (9)	0.0039 (9)	0.0072 (10)
N1	0.0235 (6)	0.0296 (8)	0.0375 (8)	0.0017 (6)	0.0030 (6)	0.0012 (7)
N2	0.0350 (8)	0.0575 (11)	0.0421 (10)	−0.0049 (8)	0.0003 (7)	−0.0064 (8)
O1	0.0311 (6)	0.0367 (7)	0.0451 (7)	−0.0088 (5)	−0.0069 (5)	−0.0010 (6)
S1	0.02191 (15)	0.0315 (2)	0.0378 (2)	−0.00129 (16)	0.00057 (16)	0.0009 (2)

C1—N1	1.458 (2)	C9—C10	1.380 (3)
C1—C3	1.476 (3)	C9—H9	0.98 (2)
C1—C2	1.551 (2)	C10—H10	1.05 (2)
C1—H1	0.998 (17)	C11—C14	1.507 (3)
C2—C5	1.512 (2)	C11—C12	1.517 (3)
C2—C4	1.523 (2)	C11—C13	1.526 (2)
C2—H2	1.046 (18)	C11—S1	1.8454 (17)
C3—N2	1.148 (2)	C12—H12A	1.02 (2)
C4—H4A	1.019 (19)	C12—H12C	0.97 (3)
C4—H4B	0.95 (2)	C12—H12B	0.99 (3)
C4—H4C	0.99 (2)	C13—H13A	1.01 (2)
C5—C6	1.391 (3)	C13—H13B	1.03 (2)
C5—C10	1.395 (2)	C13—H13C	0.99 (2)
C6—C7	1.386 (3)	C14—H14C	0.94 (2)
C6—H6	0.943 (19)	C14—H14B	1.10 (2)
C7—C8	1.390 (3)	C14—H14A	1.00 (2)
C7—H7	0.96 (2)	N1—S1	1.6560 (14)
C8—C9	1.378 (3)	N1—H01	0.89 (2)
C8—H8	1.02 (2)	O1—S1	1.4918 (12)
N1—C1—C3	111.21 (15)	C9—C10—C5	120.9 (2)
N1—C1—C2	111.10 (13)	C9—C10—H10	122.5 (11)
C3—C1—C2	111.90 (13)	C5—C10—H10	116.5 (11)
N1—C1—H1	106.6 (10)	C14—C11—C12	112.71 (17)
C3—C1—H1	106.9 (9)	C14—C11—C13	110.95 (17)
C2—C1—H1	108.8 (10)	C12—C11—C13	109.88 (17)
C5—C2—C4	114.53 (15)	C14—C11—S1	109.91 (13)
C5—C2—C1	110.36 (13)	C12—C11—S1	108.57 (14)
C4—C2—C1	108.55 (13)	C13—C11—S1	104.48 (11)
C5—C2—H2	109.2 (10)	C11—C12—H12A	110.1 (15)
C4—C2—H2	109.7 (9)	C11—C12—H12C	115.1 (16)
C1—C2—H2	104.0 (10)	H12A—C12—H12C	113 (2)
N2—C3—C1	178.3 (2)	C11—C12—H12B	109.8 (13)
C2—C4—H4A	112.9 (11)	H12A—C12—H12B	104 (2)
C2—C4—H4B	111.2 (11)	H12C—C12—H12B	104 (2)
H4A—C4—H4B	103.3 (15)	C11—C13—H13A	108.8 (13)
C2—C4—H4C	108.2 (12)	C11—C13—H13B	109.2 (12)
H4A—C4—H4C	112.6 (15)	H13A—C13—H13B	111.5 (17)
H4B—C4—H4C	108.6 (16)	C11—C13—H13C	112.4 (13)
C6—C5—C10	118.05 (17)	H13A—C13—H13C	106.7 (17)
C6—C5—C2	121.98 (15)	H13B—C13—H13C	108.3 (18)
C10—C5—C2	119.90 (16)	C11—C14—H14C	109.8 (13)
C7—C6—C5	120.94 (19)	C11—C14—H14B	112.1 (11)
C7—C6—H6	120.9 (12)	H14C—C14—H14B	109.4 (17)
C5—C6—H6	118.2 (12)	C11—C14—H14A	112.4 (13)
C6—C7—C8	120.2 (2)	H14C—C14—H14A	108.6 (17)
C6—C7—H7	118.1 (14)	H14B—C14—H14A	104.4 (18)
C8—C7—H7	121.7 (14)	C1—N1—S1	116.06 (11)
C9—C8—C7	119.2 (2)	C1—N1—H01	115.0 (12)
C9—C8—H8	120.2 (12)	S1—N1—H01	114.2 (13)
C7—C8—H8	120.4 (12)	O1—S1—N1	111.73 (7)
C8—C9—C10	120.6 (2)	O1—S1—C11	105.41 (7)
C8—C9—H9	122.8 (14)	N1—S1—C11	97.92 (7)
C10—C9—H9	116.6 (14)
N1—C1—C2—C5	172.20 (13)	C7—C8—C9—C10	1.3 (3)
C3—C1—C2—C5	47.23 (18)	C8—C9—C10—C5	0.6 (3)
N1—C1—C2—C4	−61.53 (18)	C6—C5—C10—C9	−2.1 (3)
C3—C1—C2—C4	173.50 (14)	C2—C5—C10—C9	174.84 (15)
N1—C1—C3—N2	31 (6)	C3—C1—N1—S1	−88.88 (15)
C2—C1—C3—N2	156 (6)	C2—C1—N1—S1	145.76 (12)
C4—C2—C5—C6	−39.8 (2)	C1—N1—S1—O1	90.88 (13)
C1—C2—C5—C6	83.09 (19)	C1—N1—S1—C11	−158.98 (12)
C4—C2—C5—C10	143.46 (15)	C14—C11—S1—O1	48.56 (14)
C1—C2—C5—C10	−93.69 (17)	C12—C11—S1—O1	172.26 (13)
C10—C5—C6—C7	1.6 (2)	C13—C11—S1—O1	−70.54 (14)
C2—C5—C6—C7	−175.21 (15)	C14—C11—S1—N1	−66.65 (14)
C5—C6—C7—C8	0.2 (3)	C12—C11—S1—N1	57.04 (15)
C6—C7—C8—C9	−1.7 (3)	C13—C11—S1—N1	174.25 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H01···O1i	0.89 (2)	2.167 (19)	2.9511 (18)	146.5 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H01⋯O1i	0.89 (2)	2.167 (19)	2.9511 (18)	146.5 (18)

Symmetry code: (i) .