N-[4-(β-d-Allopyranos­yloxy)benzyl­idene]methyl­amine

Shi-Ming Lv; Lei Zheng; Hui Zhao; Ying Li; Shu-Fan Yin

doi:10.1107/S1600536809000944

. 2009 Jan 10;65(Pt 2):o290. doi: 10.1107/S1600536809000944

N-[4-(β-d-Allopyranosyloxy)benzylidene]methylamine

Shi-Ming Lv ^a, Lei Zheng ^a, Hui Zhao ^a, Ying Li ^a, Shu-Fan Yin ^a,^*

PMCID: PMC2968321 PMID: 21581901

Abstract

The title compound, C₁₄H₁₉NO₆, was synthesized by the condensation reaction between hecilid (4-formylphenl-β-d-allopyranoside) and methylamine in methanol. In the crystal structure, the pyran ring adopts a chair conformation and adjacent molecules are linked by intermolecular O—H⋯O and O—H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For the pharmaceutical and biological properties of hecilid and its derivatives, see: Chen et al. (1981 ▶); Sha & Mao (1987 ▶); Zhu et al. (2006 ▶); Yang et al. (2008 ▶).

Experimental

Crystal data

C₁₄H₁₉NO₆
M _r = 297.30
Monoclinic,
a = 6.721 (4) Å
b = 7.751 (3) Å
c = 14.119 (4) Å
β = 91.46 (3)°
V = 735.3 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 292 (2) K
0.48 × 0.46 × 0.44 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
1479 measured reflections
1469 independent reflections
1325 reflections with I > 2σ(I)
R _int = 0.004
3 standard reflections every 120 reflections intensity decay: 0.8%

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.093
S = 1.09
1469 reflections
195 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: DIFRAC (Gabe et al., 1993 ▶); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000944/rz2284sup1.cif

e-65-0o290-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000944/rz2284Isup2.hkl

e-65-0o290-Isup2.hkl^{(72.4KB, 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
O2—H2O⋯O5ⁱ	0.82	2.02	2.742 (3)	147
O3—H3O⋯O2ⁱⁱ	0.82	2.14	2.942 (3)	165
O4—H4O⋯O2ⁱⁱⁱ	0.82	2.02	2.824 (3)	167
O5—H5O⋯N1^iv	0.82	1.91	2.723 (3)	170

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

Acknowledgments

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

supplementary crystallographic information

Comment

The natural compound hecilid (systematic name: 4-formylphenl-β-D-allopyranoside], which is extracted from the fruit of Helicia nilagirica Beed. (Chen et al., 1981), has been one major active ingredient of herb medicine used in China for a long time. It has manifested good biological effects on the central nervous system and a low toxicity (Sha & Mao, 1987). Some derivatives of this compound have been reported with good pharmacological activities (Zhu et al., 2006; Yang et al., 2008). The title compound, a new helicid-derived compound, was synthesized via condensation reaction of hecilid and methyl amine with good yield.

In the molecule of the title compound (Fig. 1), the average of C–C bond length in the hexatomic ring is 1.524 (3) Å; The average C(sp³)–O and C(sp²)–O bond lengths are 1.421 (3) and 1.378 (3) Å, respectively. The hexatomic ring adopts chair conformation with the hydroxy group at C3 in axial position and the other substituents at C1, C2 and C4 in equatorial positions. The C(14)–N(1)–C(13)–C(10) and C(11)–C(10)–C(13)–N(1) torsion angles are -175.7 (3) and -165.5 (3) °, respectively, possibly as a consequence of O—H···.N hydrogen bond. In the crystal packing, intermolecular O—H···.O and O—H···.N hydrogen bonds (Table 1) link the molecules into a three-dimensional network.

Experimental

A solution of helicid (1.42 g, 5 mmol) in methanol (8 ml) and a 40% aqueous solution of methyl amine (0.75 ml, 10 mmol) was subjected to ultrasonic radiation for 3 h at 333 K. On cooling to room temperature, colourless crystals were obtained unintentionally.