(S)-N-[(1S,2S)-2-Benzyl-amino-1-(4-hy-droxy-phen-yl)-3-methyl-butyl]-1,1-di-methyl-ethane-2-sulfinamide.

The title compound, C(22)H(32)N(2)O(2)S, was obtained by dehydroxy-lation and deacetyl-ation of 4-{(1S,2S)-2-(benzylhydroxy-amino)-3-methyl-1-[(S)-2-methyl-propane-2-sulfinylamino]but-yl}phenyl acetate, which was derived from reductive crosslinking of nitrone with N-tert-butane-sulfinyl-imine. The crystal structure shows that the mol-ecules are linked by O-H⋯O hydrogen bonds.

Related literature

For general background on optically pure vicinal diamines, see: Bennai & Hanessian (1997 ▶); Kizirian (2008 ▶). For the synthesis of the starting material, see: Zhong et al. (2004 ▶).

Experimental

Crystal data

C22H32N2O2S

M = 388.56

Orthorhombic,

a = 9.7503 (9) Å

b = 12.1068 (11) Å

c = 19.6292 (18) Å

V = 2317.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 293 (2) K

0.45 × 0.40 × 0.29 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.783, T max = 1.000 (expected range = 0.749–0.956)

13756 measured reflections

5016 independent reflections

2765 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.130

S = 0.89

5016 reflections

261 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Absolute structure: Flack (1983 ▶), with 2249 Friedel pairs

Flack parameter: 0.01 (10)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536808031073/bv2109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031073/bv2109Isup2.hkl

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

C22H32N2O2S	F(000) = 840
Mr = 388.56	Dx = 1.114 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2613 reflections
a = 9.7503 (9) Å	θ = 4.7–40.0°
b = 12.1068 (11) Å	µ = 0.16 mm−1
c = 19.6292 (18) Å	T = 293 K
V = 2317.1 (4) Å3	Prismatic, colourless
Z = 4	0.45 × 0.40 × 0.29 mm

Bruker SMART APEX CCD area-detector diffractometer	5016 independent reflections
Radiation source: fine-focus sealed tube	2765 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→12
Tmin = 0.784, Tmax = 1.000	k = −14→15
13756 measured reflections	l = −23→25

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0628P)2] where P = (Fo2 + 2Fc2)/3
S = 0.89	(Δ/σ)max = 0.001
5016 reflections	Δρmax = 0.17 e Å−3
261 parameters	Δρmin = −0.16 e Å−3
3 restraints	Absolute structure: Flack (1983), with 2249 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (10)

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	0.65403 (9)	0.95415 (7)	0.85995 (4)	0.0833 (3)
O1	0.7047 (3)	1.29113 (19)	0.61688 (11)	0.0852 (7)
O2	0.5196 (3)	0.9143 (2)	0.88218 (16)	0.1612 (15)
N1	0.7265 (3)	0.8691 (2)	0.80538 (11)	0.0728 (7)
N2	0.7310 (3)	0.6729 (2)	0.73797 (12)	0.0631 (6)
C1	0.6665 (3)	0.8654 (2)	0.73606 (12)	0.0632 (7)
H1	0.5697	0.8445	0.7396	0.076*
C2	0.7439 (3)	0.7739 (2)	0.69788 (12)	0.0605 (7)
H2	0.8412	0.7943	0.6988	0.073*
C3	0.7030 (4)	0.7655 (3)	0.62223 (14)	0.0791 (9)
H3	0.7041	0.8411	0.6044	0.095*
C4	0.5602 (5)	0.7234 (4)	0.61216 (19)	0.1376 (17)
H4A	0.5316	0.7378	0.5662	0.206*
H4B	0.4993	0.7602	0.6432	0.206*
H4C	0.5580	0.6454	0.6206	0.206*
C5	0.8053 (5)	0.7010 (3)	0.58036 (15)	0.1184 (14)
H5A	0.8967	0.7229	0.5926	0.178*
H5B	0.7904	0.7156	0.5329	0.178*
H5C	0.7939	0.6235	0.5890	0.178*
C6	0.6761 (3)	0.9788 (2)	0.70327 (12)	0.0590 (7)
C7	0.5600 (3)	1.0341 (3)	0.68355 (14)	0.0728 (8)
H7	0.4750	1.0008	0.6898	0.087*
C8	0.5659 (3)	1.1384 (3)	0.65456 (15)	0.0750 (8)
H8	0.4855	1.1745	0.6420	0.090*
C9	0.6911 (3)	1.1884 (2)	0.64437 (14)	0.0677 (7)
C10	0.8081 (3)	1.1331 (3)	0.66348 (15)	0.0777 (8)
H10	0.8933	1.1658	0.6568	0.093*
C11	0.7999 (3)	1.0292 (3)	0.69266 (14)	0.0736 (8)
H11	0.8801	0.9929	0.7053	0.088*
C12	0.8389 (4)	0.5915 (3)	0.73358 (17)	0.1013 (12)
H12A	0.9268	0.6284	0.7375	0.122*
H12B	0.8351	0.5565	0.6892	0.122*
C13	0.8291 (3)	0.5047 (3)	0.78733 (14)	0.0700 (8)
C14	0.8323 (3)	0.5296 (3)	0.85489 (16)	0.0841 (8)
H14	0.8391	0.6032	0.8680	0.101*
C15	0.8259 (4)	0.4497 (4)	0.90415 (16)	0.1048 (11)
H15	0.8300	0.4686	0.9500	0.126*
C16	0.8133 (5)	0.3416 (4)	0.8847 (2)	0.1146 (14)
H16	0.8085	0.2867	0.9177	0.138*
C17	0.8076 (5)	0.3137 (3)	0.8174 (2)	0.1120 (13)
H17	0.7971	0.2404	0.8043	0.134*
C18	0.8176 (4)	0.3956 (3)	0.76973 (17)	0.0913 (10)
H18	0.8166	0.3766	0.7238	0.110*
C19	0.7700 (5)	0.9328 (3)	0.93164 (15)	0.1022 (13)
C20	0.9065 (5)	0.9748 (6)	0.9100 (3)	0.184 (2)
H20A	0.9624	0.9878	0.9495	0.276*
H20B	0.8952	1.0427	0.8853	0.276*
H20C	0.9502	0.9212	0.8813	0.276*
C21	0.7701 (9)	0.8136 (3)	0.95298 (19)	0.187 (4)
H21A	0.8172	0.7703	0.9194	0.325*
H21B	0.6773	0.7880	0.9571	0.325*
H21C	0.8158	0.8064	0.9961	0.325*
C22	0.7108 (6)	1.0067 (3)	0.98828 (17)	0.1491 (19)
H22A	0.7718	1.0066	1.0267	0.224*
H22B	0.6228	0.9788	1.0020	0.224*
H22C	0.7007	1.0807	0.9715	0.224*
H1A	0.738 (3)	0.8013 (15)	0.8199 (13)	0.065 (9)*
H2A	0.651 (2)	0.645 (3)	0.7369 (16)	0.094 (12)*
H1B	0.634 (3)	1.329 (3)	0.614 (2)	0.15 (2)*

	U11	U22	U33	U12	U13	U23
S1	0.1059 (7)	0.0689 (5)	0.0750 (5)	−0.0119 (5)	0.0166 (4)	−0.0222 (4)
O1	0.1074 (19)	0.0627 (15)	0.0853 (15)	0.0058 (14)	0.0131 (13)	0.0169 (12)
O2	0.135 (2)	0.174 (3)	0.175 (3)	−0.068 (2)	0.076 (2)	−0.113 (2)
N1	0.1051 (19)	0.0633 (17)	0.0501 (13)	0.0144 (15)	0.0058 (12)	0.0019 (13)
N2	0.0687 (18)	0.0526 (15)	0.0680 (15)	0.0056 (13)	0.0095 (12)	0.0088 (12)
C1	0.0726 (18)	0.0592 (17)	0.0579 (15)	0.0020 (15)	−0.0025 (15)	0.0007 (14)
C2	0.0737 (18)	0.0556 (17)	0.0524 (14)	−0.0021 (14)	0.0000 (14)	0.0042 (13)
C3	0.119 (3)	0.0614 (19)	0.0570 (17)	−0.0054 (19)	−0.0165 (17)	0.0032 (15)
C4	0.151 (4)	0.160 (4)	0.101 (3)	−0.011 (3)	−0.056 (3)	−0.019 (3)
C5	0.173 (4)	0.130 (3)	0.0521 (17)	0.028 (3)	−0.003 (2)	−0.018 (2)
C6	0.0635 (17)	0.0550 (17)	0.0584 (14)	0.0033 (15)	0.0039 (13)	−0.0034 (13)
C7	0.072 (2)	0.065 (2)	0.0817 (19)	0.0047 (16)	0.0077 (15)	0.0019 (18)
C8	0.082 (2)	0.065 (2)	0.077 (2)	0.0141 (17)	0.0021 (17)	0.0095 (17)
C9	0.088 (2)	0.0566 (18)	0.0590 (15)	0.0067 (17)	0.0086 (16)	−0.0019 (15)
C10	0.074 (2)	0.070 (2)	0.090 (2)	−0.0025 (17)	−0.0012 (17)	0.0027 (18)
C11	0.073 (2)	0.063 (2)	0.0848 (19)	0.0046 (16)	−0.0082 (15)	0.0026 (17)
C12	0.113 (3)	0.090 (2)	0.101 (2)	0.036 (2)	0.036 (2)	0.032 (2)
C13	0.0714 (19)	0.074 (2)	0.0646 (17)	0.0123 (17)	0.0114 (15)	0.0132 (16)
C14	0.094 (2)	0.072 (2)	0.086 (2)	−0.0030 (19)	0.0030 (19)	−0.003 (2)
C15	0.142 (3)	0.112 (3)	0.0610 (18)	−0.002 (3)	0.002 (2)	0.011 (2)
C16	0.164 (4)	0.085 (3)	0.094 (3)	0.016 (3)	0.016 (3)	0.030 (2)
C17	0.164 (4)	0.071 (2)	0.101 (3)	0.012 (3)	0.019 (3)	0.009 (2)
C18	0.116 (3)	0.079 (3)	0.079 (2)	0.009 (2)	0.000 (2)	−0.0023 (19)
C19	0.181 (4)	0.070 (2)	0.0555 (17)	−0.014 (2)	−0.002 (2)	−0.0059 (17)
C20	0.140 (4)	0.283 (8)	0.130 (4)	−0.007 (5)	−0.052 (3)	−0.018 (5)
C21	0.309 (12)	0.076 (3)	0.065 (2)	0.030 (4)	−0.043 (4)	−0.003 (2)
C22	0.249 (6)	0.111 (3)	0.087 (2)	−0.012 (3)	0.005 (3)	−0.047 (2)

S1—O2	1.463 (3)	C9—C10	1.374 (4)
S1—N1	1.645 (2)	C10—C11	1.385 (4)
S1—C19	1.824 (4)	C10—H10	0.9300
O1—C9	1.363 (3)	C11—H11	0.9300
O1—H1B	0.828 (19)	C12—C13	1.492 (4)
N1—C1	1.481 (3)	C12—H12A	0.9700
N1—H1A	0.875 (17)	C12—H12B	0.9700
N2—C12	1.443 (4)	C13—C14	1.360 (4)
N2—C2	1.460 (3)	C13—C18	1.370 (4)
N2—H2A	0.847 (18)	C14—C15	1.369 (4)
C1—C6	1.520 (4)	C14—H14	0.9300
C1—C2	1.536 (4)	C15—C16	1.368 (5)
C1—H1	0.9800	C15—H15	0.9300
C2—C3	1.541 (4)	C16—C17	1.364 (5)
C2—H2	0.9800	C16—H16	0.9300
C3—C4	1.496 (5)	C17—C18	1.368 (5)
C3—C5	1.510 (5)	C17—H17	0.9300
C3—H3	0.9800	C18—H18	0.9300
C4—H4A	0.9600	C19—C20	1.487 (6)
C4—H4B	0.9600	C19—C21	1.502 (5)
C4—H4C	0.9600	C19—C22	1.539 (5)
C5—H5A	0.9600	C20—H20A	0.9600
C5—H5B	0.9600	C20—H20B	0.9600
C5—H5C	0.9600	C20—H20C	0.9600
C6—C11	1.368 (4)	C21—H21A	0.9600
C6—C7	1.371 (4)	C21—H21B	0.9600
C7—C8	1.386 (4)	C21—H21C	0.9600
C7—H7	0.9300	C22—H22A	0.9600
C8—C9	1.378 (4)	C22—H22B	0.9600
C8—H8	0.9300	C22—H22C	0.9600
O2—S1—N1	111.86 (14)	C9—C10—H10	119.8
O2—S1—C19	106.2 (2)	C11—C10—H10	119.8
N1—S1—C19	98.49 (15)	C6—C11—C10	121.2 (3)
C9—O1—H1B	117 (3)	C6—C11—H11	119.4
C1—N1—S1	116.59 (19)	C10—C11—H11	119.4
C1—N1—H1A	108.7 (18)	N2—C12—C13	113.1 (2)
S1—N1—H1A	115.4 (18)	N2—C12—H12A	109.0
C12—N2—C2	118.5 (2)	C13—C12—H12A	109.0
C12—N2—H2A	114 (2)	N2—C12—H12B	109.0
C2—N2—H2A	113 (2)	C13—C12—H12B	109.0
N1—C1—C6	109.7 (2)	H12A—C12—H12B	107.8
N1—C1—C2	106.0 (2)	C14—C13—C18	117.5 (3)
C6—C1—C2	114.5 (2)	C14—C13—C12	122.1 (3)
N1—C1—H1	108.8	C18—C13—C12	120.4 (3)
C6—C1—H1	108.8	C13—C14—C15	122.1 (3)
C2—C1—H1	108.8	C13—C14—H14	119.0
N2—C2—C1	107.4 (2)	C15—C14—H14	119.0
N2—C2—C3	116.2 (2)	C16—C15—C14	118.8 (3)
C1—C2—C3	113.0 (2)	C16—C15—H15	120.6
N2—C2—H2	106.5	C14—C15—H15	120.6
C1—C2—H2	106.5	C17—C16—C15	120.7 (3)
C3—C2—H2	106.5	C17—C16—H16	119.6
C4—C3—C5	111.5 (3)	C15—C16—H16	119.6
C4—C3—C2	113.0 (3)	C16—C17—C18	118.7 (4)
C5—C3—C2	112.8 (3)	C16—C17—H17	120.7
C4—C3—H3	106.3	C18—C17—H17	120.7
C5—C3—H3	106.3	C17—C18—C13	122.2 (3)
C2—C3—H3	106.3	C17—C18—H18	118.9
C3—C4—H4A	109.5	C13—C18—H18	118.9
C3—C4—H4B	109.5	C20—C19—C21	114.1 (5)
H4A—C4—H4B	109.5	C20—C19—C22	110.1 (4)
C3—C4—H4C	109.5	C21—C19—C22	110.9 (3)
H4A—C4—H4C	109.5	C20—C19—S1	106.6 (3)
H4B—C4—H4C	109.5	C21—C19—S1	110.6 (3)
C3—C5—H5A	109.5	C22—C19—S1	104.0 (3)
C3—C5—H5B	109.5	C19—C20—H20A	109.5
H5A—C5—H5B	109.5	C19—C20—H20B	109.5
C3—C5—H5C	109.5	H20A—C20—H20B	109.5
H5A—C5—H5C	109.5	C19—C20—H20C	109.5
H5B—C5—H5C	109.5	H20A—C20—H20C	109.5
C11—C6—C7	117.9 (3)	H20B—C20—H20C	109.5
C11—C6—C1	121.4 (3)	C19—C21—H21A	109.5
C7—C6—C1	120.7 (3)	C19—C21—H21B	109.5
C6—C7—C8	121.8 (3)	H21A—C21—H21B	109.5
C6—C7—H7	119.1	C19—C21—H21C	109.5
C8—C7—H7	119.1	H21A—C21—H21C	109.5
C9—C8—C7	119.8 (3)	H21B—C21—H21C	109.5
C9—C8—H8	120.1	C19—C22—H22A	109.5
C7—C8—H8	120.1	C19—C22—H22B	109.5
O1—C9—C10	118.2 (3)	H22A—C22—H22B	109.5
O1—C9—C8	123.0 (3)	C19—C22—H22C	109.5
C10—C9—C8	118.8 (3)	H22A—C22—H22C	109.5
C9—C10—C11	120.5 (3)	H22B—C22—H22C	109.5
O2—S1—N1—C1	72.0 (3)	O1—C9—C10—C11	179.0 (2)
C19—S1—N1—C1	−176.7 (2)	C8—C9—C10—C11	−0.2 (4)
S1—N1—C1—C6	60.5 (3)	C7—C6—C11—C10	0.6 (4)
S1—N1—C1—C2	−175.33 (19)	C1—C6—C11—C10	−179.2 (2)
C12—N2—C2—C1	−151.5 (3)	C9—C10—C11—C6	−0.1 (5)
C12—N2—C2—C3	80.9 (4)	C2—N2—C12—C13	167.6 (3)
N1—C1—C2—N2	55.6 (3)	N2—C12—C13—C14	−59.0 (5)
C6—C1—C2—N2	176.7 (2)	N2—C12—C13—C18	121.6 (4)
N1—C1—C2—C3	−174.9 (2)	C18—C13—C14—C15	0.7 (5)
C6—C1—C2—C3	−53.8 (3)	C12—C13—C14—C15	−178.8 (3)
N2—C2—C3—C4	55.6 (4)	C13—C14—C15—C16	−1.2 (6)
C1—C2—C3—C4	−69.3 (4)	C14—C15—C16—C17	0.2 (7)
N2—C2—C3—C5	−72.1 (4)	C15—C16—C17—C18	1.3 (7)
C1—C2—C3—C5	163.1 (3)	C16—C17—C18—C13	−1.9 (6)
N1—C1—C6—C11	60.3 (3)	C14—C13—C18—C17	0.9 (5)
C2—C1—C6—C11	−58.7 (3)	C12—C13—C18—C17	−179.6 (3)
N1—C1—C6—C7	−119.5 (3)	O2—S1—C19—C20	−179.0 (3)
C2—C1—C6—C7	121.5 (3)	N1—S1—C19—C20	65.2 (3)
C11—C6—C7—C8	−0.9 (4)	O2—S1—C19—C21	56.4 (4)
C1—C6—C7—C8	178.9 (2)	N1—S1—C19—C21	−59.4 (4)
C6—C7—C8—C9	0.6 (4)	O2—S1—C19—C22	−62.7 (3)
C7—C8—C9—O1	−179.2 (3)	N1—S1—C19—C22	−178.5 (3)
C7—C8—C9—C10	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···O2i	0.83 (2)	1.82 (2)	2.647 (4)	173 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯O2i	0.828 (19)	1.82 (2)	2.647 (4)	173 (5)

Symmetry code: (i) .