(8S,9S,10R)-4-(4-Chloro­benz­yloxy)-7,8-didehydro-3,7-dimeth­oxy-17-methyl­morphinan-6-one monohydrate

Xing-Liang Zheng; Shu-Jun Chen; Ning-Fei Jiang; Sue-Hui Zhan

doi:10.1107/S1600536811013973

. 2011 Apr 22;67(Pt 5):o1190. doi: 10.1107/S1600536811013973

(8S,9S,10R)-4-(4-Chlorobenzyloxy)-7,8-didehydro-3,7-dimethoxy-17-methylmorphinan-6-one monohydrate

Xing-Liang Zheng ^a,^*, Shu-Jun Chen ^a, Ning-Fei Jiang ^a, Sue-Hui Zhan ^a

PMCID: PMC3089213 PMID: 21754492

Abstract

In the title compound, C₂₆H₂₈Cl_NO₄·H₂O, the dihedral angle betwene the two aromatic rings is 69.73 (6)°. The N-containing ring exhibits a chair conformation, while the other non-aromatic rings are in approximate envelope conformations. In the crystal, the water molecule forms O—H⋯O and O—H⋯N hydrogen bonds and a C—H⋯O link also occurs.

Related literature

For background to the biological activity of sinomenine derivatives and other related compounds, see: Liu et al. (1994 ▶, 1996 ▶, 1997 ▶); Mark et al. (2003 ▶); Ye et al. (2004 ▶). For the synthesis of the title compound, see: Mitsunobu (1981 ▶). For related structures, see: Li et al. (2009 ▶); Batterham et al. (1965 ▶).

Experimental

Crystal data

C₂₆H₂₈ClNO₄·H₂O
M _r = 471.96
Monoclinic,
a = 8.8866 (4) Å
b = 14.6386 (7) Å
c = 9.1860 (4) Å
β = 91.618 (1)°
V = 1194.51 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.45 × 0.36 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.917, T _max = 0.940
13795 measured reflections
4185 independent reflections
3974 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.082
S = 1.05
4185 reflections
303 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 1991 Friedel pairs
Flack parameter: −0.02 (6)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013973/kp2320sup1.cif

e-67-o1190-sup1.cif^{(25KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013973/kp2320Isup2.hkl

e-67-o1190-Isup2.hkl^{(205.1KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1ⁱ	0.98	2.56	3.469 (2)	155
O1W—H1WB⋯O4ⁱⁱ	0.85	2.04	2.879 (2)	169
O1W—H1WA⋯N1	0.85	2.16	2.899 (2)	146

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The project was supported by the National Natural Science Foundation of China (No. 20976017) and the Scientific Research Fund of Hunan Provincial Science and Technology Department of China (No. 2009 C K3070).

supplementary crystallographic information

Comment

We synthesised a new sinomenine derivative (8S,9S,10R)-7,8-didehydro-4-(4'-chlorobenzyloxy)-3,7-\ dimethoxy-17-methyl-morphinan-6-one monohydrate. Herein, its crystal structure is reported. Biological effects of sinomenine derivatives and related compounds have been described (Liu et al., 1994, 1996, 1997; Mark et al., 2003; Ye et al., 2004).

The molecular structure of (I) is shown in Fig. 1. The angle between the two benzene planes is 69.736°. Rings C [C9/C10/C11/C12/C13/C14] and B [C5···.C10], both, are in an envelope conformation. In contrast, ring D [C8/N1/C15/C16/C10/C9] exhibits an almost regular chair conformation. Similar features have been described in related compounds (Li et al., 2009; Batterham et al., 1965). The crystal structure is stabilised by O—H···O and O—H···N hydrogen bonds linking sinomenine derivative and the water molecule; weak C—H···O hydrogen bonds (Table 1 and Fig. 2) also occurred.

Experimental

The title compound was obtained according to the method of Mitsunobu (1981). Colourless blocks of (I) were grown from an acetic ether solution.