(S)-N-[(1S,2S)-2-Benzyl­amino-1-(4-hy­droxy­phen­yl)-3-methyl­butyl]-1,1-di­methyl­ethane-2-sulfinamide

Shen, C.

doi:10.1107/S1600536808031073

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2082

doi:10.1107/S1600536808031073

Open

access

(S)-N-[(1S,2S)-2-Benzylamino-1-(4-hydroxyphenyl)-3-methylbutyl]-1,1-dimethylethane-2-sulfinamide

Chun Shen ^a ^*

^aDepartment of Chemistry, East China Normal University, 3663 Zhongshan Road, Shanghai 200062, People's Republic of China
^*Correspondence e-mail: fengcg@mail.sioc.ac.cn

(Received 5 September 2008; accepted 25 September 2008; online 9 October 2008)

The title compound, C₂₂H₃₂N₂O₂S, was obtained by dehydroxylation and deacetylation of 4-{(1S,2S)-2-(benzylhydroxyamino)-3-methyl-1-[(S)-2-methylpropane-2-sulfinylamino]butyl}phenyl acetate, which was derived from reductive crosslinking of nitrone with N-tert-butanesulfinylimine. The crystal structure shows that the molecules 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_r = 388.56
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.130
S = 0.89
5016 reflections
261 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), with 2249 Friedel pairs
Flack parameter: 0.01 (10)

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031073/bv2109sup1.cif

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

checkCIF report

Comment top

Optically pure vicinal diamines are important molecules due to their special structures. Among them, a lot of compounds have been used as catalysts in asymmetric reactions (Bennai & Hanessian, 1997; Kizirian, 2008). In our study of vicinal diamines, we prepared (S)-N-((1S,2S)-2-(benzylamino)-1-(4-hydroxyphenyl) -3-methylbutyl)-2-methylpropane-2-sulfinamide through dehydroxylation and deacetylation of acetic acid 4-[(1S,2S)-2(benzyl-hydroxy-amino)-3-methyl-1- ((S)-2-methyl-propane-2-sulfinylamino)-butyl]-phenyl ester which was prepared according to the reported procedure (Zhong et al., 2004). Here, we report its crystal structure. The molecules are linked by a strong intermolecular O1—H1B···O2ⁱ hydrogen interaction. The molecular packing for the compound is shown in Fig. 3, where hydrogen bond interactions are shown as dashed lines. The two benzene rings are almost perpendicular to each other, making a diheral angle of 84.12(0.12)°. The molecule exists in a trans configuration with an N1—C1—C2—N2 torsion angle of 55.6 (3)°. The absolute configuration was known from the starting chiral material and is confirmed by this X-ray analysis.

Related literature top

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 top

A mixture of Cu(II) acetate (18 mg, 0.1 mmol), zinc powder (324 mg, 5.0 mmol) and acetic acid (2 ml) was stirred for 15 minutes under a nitrogen atmosphere at room temperature. Then a mixture of acetic acid (2 ml), distilled water (0.7 ml) and acetic acid 4-[(1S,2S)-2(benzyl-hydroxy-amino)-3-methyl -1-((S)-2-methyl-propane-2-sulfinylamino)-butyl]-phenyl ester (Zhong et al., 2004) (446 mg, 1.0 mmol) was added. The resulting mixture was heated to 343 K and stirred for an hour. After cooling to room temperature, ethylene diamine tetraacetic acid disodium salt (0.5 g) was added and stirred for 10 minutes. Aqueous KOH (3N) solution was then added to adjust the mixture to a pH value of 10. The resulting solution was extracted with ethyl acetate, and the combined organic layers were washed with saturated aqueous ethylene diamine tetraacetic acid disodium salt and brine successively. Concentrated under reduced pressure, the crude product was dissolved in MeOH (10 ml) and saturated aqueous NaHCO₃ (10 ml) was added. The mixture was stirred for 12 h at room temperature and then MeOH was removed under reduced pressure. The crude solid was redissolved in CH₂Cl₂, washed with brine and dried with anhydrous Na₂SO₄. After silica gel chromatography, the pure product was obtained as a white solid (yield 77% over two steps). Suitable crystals for the X-ray diffraction experiment were obtained by recrystalization from hexane/CH₂Cl₂ (3:1). Spectroscopic data: ¹H NMR (300 MHz, CDCl₃) δ 7.36–7.24 (m, 5H), 7.11 (d, J = 6.0 Hz, 2H), 6.80 (d, J = 5.7 Hz, 2H), 5.49 (s, 1H), 4.02 (m, 2H), 3.77 (d, J = 13.2 Hz, 1H), 2.63(d, J = 9.3 Hz, 1H), 1.72 (m, 2H), 1.14 (s, 9H), 0.95 (d, J = 4.5 Hz, 3H), 0.77 (d, J = 4.5 Hz, 3H). ESI-MS (m/z): 389(M+H⁺).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. Plot of C₂₂H₃₂N₂O₂S at the 50% probability level. H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Hydrogen bonding in the title compound. Symmetry codes: (i) -x + 1, y + 1/2, -z + 3/2.
	Fig. 3. Molecular packing plot, viewed along a axis. Hydrogen bond interactions are shown as dashed lines.

(S)-N-[(1S,2S)-2-Benzylamino-1-(4-hydroxyphenyl)- 3-methylbutyl]-1,1-dimethylethane-2-sulfinamide top

Crystal data top

C₂₂H₃₂N₂O₂S	F(000) = 840
M_r = 388.56	D_x = 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

Data collection top

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

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0628P)²] where P = (F_o² + 2F_c²)/3
S = 0.89	(Δ/σ)_max = 0.001
5016 reflections	Δρ_max = 0.17 e Å⁻³
261 parameters	Δρ_min = −0.16 e Å⁻³
3 restraints	Absolute structure: Flack (1983), with 2249 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (10)

Crystal data top

C₂₂H₃₂N₂O₂S	V = 2317.1 (4) Å³
M_r = 388.56	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.7503 (9) Å	µ = 0.16 mm⁻¹
b = 12.1068 (11) Å	T = 293 K
c = 19.6292 (18) Å	0.45 × 0.40 × 0.29 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5016 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2765 reflections with I > 2σ(I)
T_min = 0.784, T_max = 1.000	R_int = 0.038
13756 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.130	Δρ_max = 0.17 e Å⁻³
S = 0.89	Δρ_min = −0.16 e Å⁻³
5016 reflections	Absolute structure: Flack (1983), with 2249 Friedel pairs
261 parameters	Absolute structure parameter: 0.01 (10)
3 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	0.65403 (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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (i) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₃₂N₂O₂S
M_r	388.56
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.7503 (9), 12.1068 (11), 19.6292 (18)
V (Å³)	2317.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.45 × 0.40 × 0.29

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.784, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13756, 5016, 2765
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.130, 0.89
No. of reflections	5016
No. of parameters	261
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16
Absolute structure	Flack (1983), with 2249 Friedel pairs
Absolute structure parameter	0.01 (10)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y+1/2, −z+3/2.

References

Bennai, Y. L. & Hanessian, S. (1997). Chem. Rev. 97, 3161–3196. PubMed Google Scholar
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kizirian, J. C. (2008). Chem. Rev. 108, 140–205. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhong, Y.-W., Xu, M.-H. & Lin, G.-Q. (2004). Org. Lett. 6, 3953–3956. Web of Science CSD CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2082

doi:10.1107/S1600536808031073

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(S)-N-[(1S,2S)-2-Benzyl­amino-1-(4-hy­dr­oxy­phen­yl)-3-methyl­butyl]-1,1-di­methyl­ethane-2-sulfinamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(S)-N-[(1S,2S)-2-Benzylamino-1-(4-hydroxyphenyl)-3-methylbutyl]-1,1-dimethylethane-2-sulfinamide