9-[(2-Chloro­benz­yl)amino]-5-(3,4,5-trimeth­oxy­phen­yl)-5,5a,8a,9-tetra­hydro­furo[3′,4′:6,7]naphtho­[2,3-d][1,3]dioxol-6(8H)-one

Tie-Liang Zhu; Jie-Ru Jin; Hong Chen; Li-Ting Chen; Jing Liu

doi:10.1107/S1600536811018289

. 2011 May 25;67(Pt 6):o1491. doi: 10.1107/S1600536811018289

9-[(2-Chlorobenzyl)amino]-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3′,4′:6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

Tie-Liang Zhu ^a, Jie-Ru Jin ^b, Hong Chen ^c,^d, Li-Ting Chen ^d, Jing Liu ^d,^*

PMCID: PMC3120584 PMID: 21754859

Abstract

In the title compound, C₂₉H₂₈ClNO₇, the tetrahydrofuran ring and the six-membered ring fused to it both display envelope conformations. The dihedral angles between the plane of the benzene ring of the benzo[d][1,3]dioxole system and the planes of the other two benzene rings are 80.59 (3) and 63.60 (2)°.

Related literature

For bond-length and angle data for similar structures, see: Feng et al. (2008 ▶); Zhang et al. (1994 ▶); Zuo et al. (2009 ▶).

Experimental

Crystal data

C₂₉H₂₈ClNO₇
M _r = 537.97
Orthorhombic,
a = 10.0971 (14) Å
b = 15.264 (2) Å
c = 16.220 (2) Å
V = 2499.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2007 ▶) T _min = 0.960, T _max = 0.976
26247 measured reflections
5968 independent reflections
5580 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.031
wR(F ²) = 0.066
S = 1.03
5968 reflections
350 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983), 2615 Friedel pairs
Flack parameter: 0.00 (4)

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018289/hg5035sup1.cif

e-67-o1491-sup1.cif^{(26.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018289/hg5035Isup2.hkl

e-67-o1491-Isup2.hkl^{(292.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811018289/hg5035Isup3.cml

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
C26—H26⋯O7ⁱ	0.95	2.56	3.2130 (18)	126

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 30873363), the Program of the Science Foundation of Tianjin (08JCYBJC070000) and the Major Program of the Science Foundation of Tianjin (09ZCKFSH01700).

supplementary crystallographic information

Comment

Podophyllotoxin and their derivatives are well known as substances with anti-cancer activity. In recent years, our study are paying attention to synthesize different kinds of Podophyllotoxin compounds and aim at the discovery of new derivatives with improved bioactivities. In this paper, we reported the crystal structure of title compound.

In title compound, C₂₉H₂₈ClNO₇, bond lengths and angles are normal and in good agreement with those reported previously (Feng et al., 2008; Zhang, et al., 1994; Zuo, et al., 2009). The tetrahydrofuran ring (C1/C2/C12/C30/O3) and the six-membered ring (C2—C4/C10—C12)fused to it both display envelope conformations. The dihedral angles between the benzene ring (C4—C10) of the benzo[d]-[1,3]dioxole and the other two benzene ring (C13—C18 and C23—C28) are 80.59 (3) and 63.60 (2)°, respectively. There are weaker C—H···O intermolecular interactions, which stabilized the structure (Table 1).

Experimental

The target compound was synthesized by two steps. 2-chlorobenzaldehyde, 4β-amino podophyllotoxin, two drops of acetic acid in 95% ethanol was stirred for 6 h. Appropriate amount of NaBH₄ was added into the reaction mixture to stirred for 1 h at 273 K. Then add 5% HCl to end off the reaction, the reaction mixture was concentrated in vacuo. Add saturated NaHCO₃ to adjust PH>7. The reaction mixture was extracted with CH₂Cl₂ and dried over MgSO₄ and concentrated in vacuo. The residue was resolved in a methanol solution and slow evaporation over two weeks at room temperature gave transparent crystals suitable for X-ray analysis.