{(1R,3S)-2-Benzyl-6,7-dimeth­oxy-1-phenyl-1,2,3,4-tetra­hydro­isoquinolin-3-yl}diphenyl­methanol

Naicker, T.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.

doi:10.1107/S1600536810005295

Volume 66
Part 3
Page o638
March 2010

Received 24 January 2010
Accepted 9 February 2010
Online 17 February 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.025
wR = 0.068
Data-to-parameter ratio = 6.7
Details

{(1R,3S)-2-Benzyl-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl}diphenylmethanol

Tricia Naicker,^a ^* Thavendran Govender,^b Hendrik G. Kruger ^a and Glenn E.M. Maguire ^a

^aSchool of Chemistry, University of KwaZulu-Natal, Durban, 4000, South Africa, and ^bSchool of Pharmacy and Pharmacology, University of KwaZulu-Natal, Durban, 4000, South Africa
Correspondence e-mail: govenderthav@ukzn.ac.za

In the title compound, C₃₇H₃₅NO₃, a precursor to novel chiral catalysts, the N-containing six-membered ring assumes a half-chair conformation. Intermolecular C-HO hydrogen bonds link the molecules in the crystal structure.

Related literature

For the synthesis of the title compound, see: Chakka et al. (2010). For related structures, see: Aubry et al. (2006). For a related structure with the same chiral centres and configuration, see: Naicker et al. (2009). For proline diaryl alcohols, see: Diner et al. (2008); Seebach et al. (2008).

Experimental

Crystal data

C₃₇H₃₅NO₃
M_r = 541.66
Monoclinic, P 2₁
a = 11.9706 (5) Å
b = 10.1934 (4) Å
c = 13.1515 (5) Å
= 116.546 (2)°
V = 1435.58 (10) Å³
Z = 2
Cu K radiation
= 0.62 mm^-1
T = 173 K
0.22 × 0.14 × 0.12 mm

Data collection

Bruker Kappa Duo APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006) T_min = 0.876, T_max = 0.930
15262 measured reflections
2514 independent reflections
2451 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.025
wR(F²) = 0.068
S = 1.10
2514 reflections
375 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.14 e Å^-3
_min = -0.12 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15O2ⁱ	0.95	2.44	3.385 (2)	171
Symmetry code: (i) x, y, z-1.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2135 ).

Acknowledgements

The authors wish to thank Dr Hong Su of the Chemistry Department of the University of Cape Town for her assistance with the crystallographic data collection and Dr M Bala of the School of Chemistry at University of KwaZulu-Natal for his assistance with preparation of this manuscript.

References

Aubry, S., Pellet-Rostaing, S., Faure, R. & Lemaire, M. (2006). J. Heterocycl. Chem, 43, 139-148.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2006). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakka, S. K., Andersson, P. G., Maguire, G. E. M., Kruger, H. G. & Govender, T. (2010). Eur. J. Org. Chem. pp. 972-980
Diner, P., Kjaersgaard, A., Lie, M. A. & Jorgensen, K. A. (2008). Chem. Eur. J. 14, 122-127.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Naicker, T., McKay, M., Govender, T., Kruger, H. G. & Maguire, G. E. M. (2009). Acta Cryst. E65, o3278.
Seebach, D., Groselj, U., Badine, D. M., Schweizer, W. B. & Beck, A. K. (2008). Helv. Chim. Acta, 91, 1999-2034
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds