(1′S,2R,3R)-(−)-2-Hydr­oxy-3-morpholino-3-phenyl-N-(1′-phenyl­ethyl)propion­amide

Mendoza, A.; Aparicio, D.M.; Terán, J.L.; Gnecco, D.; Juárez, J.R.

doi:10.1107/S1600536809008198

Volume 65
Part 4
Page o743
April 2009

Received 3 March 2009
Accepted 5 March 2009
Online 14 March 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R = 0.054
wR = 0.163
Data-to-parameter ratio = 11.8
Details

(1'S,2R,3R)-(-)-2-Hydroxy-3-morpholino-3-phenyl-N-(1'-phenylethyl)propionamide

Angel Mendoza,^a ^* David M. Aparicio,^a Joel L. Terán,^a Dino Gnecco ^a and Jorge R. Juárez ^a

^aCentro de Química, ICUAP, Benemérita Universidad Autónoma de Puebla, Puebla, Puebla, Mexico
Correspondence e-mail: angel.mendoza.m@gmail.com

In the title compound, C₂₁H₂₆N₂O₃, the morpholine ring has a chair conformation and the dihedral angle between the two phenyl rings is 59.0 (3)°. The crystal packing is stabilized by intermolecular O-HO hydrogen bonds, generating a ribbon structure along the a axis. An intramolecular N-HO contact is also present.

Related literature

For general background, see: Barbaro et al. (1992); Szymanski et al. (2006); Sheppard et al. (2004); Chen et al. (1996); Concellón et al. (2003a,b); Martín et al. (2004). For related structures, see: Romero et al. (2005a,b). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₁H₂₆N₂O₃
M_r = 354.44
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.0010 (17) Å
b = 15.659 (3) Å
c = 20.746 (4) Å
V = 1949.5 (8) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 K
0.72 × 0.28 × 0.16 mm

Data collection

Bruker P4 diffractometer
Absorption correction: none
3964 measured reflections
2959 independent reflections
1116 reflections with I > 2(I)
R_int = 0.055
3 standard reflections every 97 reflections intensity decay: 3%

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.163
S = 0.89
2959 reflections
251 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.24 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1	1.00 (7)	1.92 (7)	2.569 (5)	120 (5)
O1-H1OO2ⁱ	0.98 (8)	1.80 (8)	2.753 (4)	163 (7)
Symmetry code: (i) x-1, y, z.

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2398 ).

Acknowledgements

We acknowledge financial support under scholarship DMAS No. 169011 and CONACyT project No. 83185. Special thanks go to Dr Marcos Flores (USAI-FQ-UNAM) for useful comments.

References

Barbaro, G., Battaglia, A. & Giorgianni, P. (1992). J. Org. Chem. 57, 5128-5136.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.
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Concellón, J. M. & Bardales, E. (2003a). Org. Lett. 5, 4783-4785.
Concellón, J. M. & Bardales, E. (2003b). Tetrahedron Lett. 44, 5323-5326.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
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Romero, N., Terán, J. L., Gnecco, D. & Bernès, S. (2005a). Acta Cryst. E61, o2924-o2926.
Romero, N., Terán, J. L., Gnecco, D. & Bernès, S. (2005b). Acta Cryst. E61, o2927-o2929.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sheppard, G. S., Wang, J., Kawai, M., BaMaung, N. T., Craig, R. A., Erickson, S. A., Lynch, L., Patel, J., Yang, F., Searle, X. B., Lou, P., Park, C., Kim, K. H., Henkin, J. & Lesniewski, R. (2004). Bioorg. Med. Chem. Lett. 14, 865-868.
Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Szymanski, W. & Ostaszewski, R. (2006). Tetrahedron Asymmetry, 17, 2667-2671.

organic compounds