Dihydro­allocryptopine

Wenwen Sun; Yuyan Qin; Zhe Hou; Yao Yao; Le Zhou

doi:10.1107/S1600536811052172

. 2011 Dec 10;68(Pt 1):o69. doi: 10.1107/S1600536811052172

Dihydroallocryptopine

Wenwen Sun ^a, Yuyan Qin ^a, Zhe Hou ^a, Yao Yao ^a, Le Zhou ^a,^*

PMCID: PMC3254424 PMID: 22259569

Abstract

In the title compound [systematic name: 7,8-dimethoxy-11-methyl-17,19-dioxa-11-azatetracyclo[12.7.0.0^4,9.0^16,20]henicosa-1(21),4,6,8,14,16 (20)-hexaen-2-ol], C₂₁H₂₅NO₅, the benzene rings are inclined at a dihedral angle of 23.16 (5)°. One of the methoxy C atoms is close to coplanar with its attached ring [deviation = 0.129 (3) Å], whereas the other is orientated away from the ring [deviation = −1.124 (2) Å]. The 10-membered ring is highly puckered, and the OH and CH₃ substituents project to the same side of the ring. In the crystal, O—H⋯O hydrogen bonds link the molecules into [010] chains and C—H⋯O and C—H⋯π interactions consolidate the packing.

Related literature

For the synthesis of the title compound, see: Wada et al. (2007 ▶). For the biological activity of allocryptopine derivatives, see: Morteza et al. (2003 ▶); Yan et al. (2009 ▶); Capasso et al. (1997 ▶); Jeong et al. (2009 ▶); Zhao et al. (2008 ▶). For a related structure, see: Valpuesta et al. (2006 ▶).

Experimental

Crystal data

C₂₁H₂₅NO₅
M _r = 371.42
Monoclinic,
a = 14.2557 (19) Å
b = 9.3705 (13) Å
c = 15.278 (2) Å
β = 106.601 (2)°
V = 1955.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.45 × 0.24 × 0.21 mm

Data collection

Bruker SMART APEX II CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.961, T _max = 0.981
14189 measured reflections
3646 independent reflections
2766 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.110
S = 1.02
3646 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811052172/hb6507sup1.cif

e-68-00o69-sup1.cif^{(22.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052172/hb6507Isup2.hkl

e-68-00o69-Isup2.hkl^{(178.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811052172/hb6507Isup3.cml

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

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

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5ⁱ	0.82	2.03	2.8380 (16)	168
C7—H7A⋯O4ⁱⁱ	0.97	2.57	3.405 (3)	144
C18—H18⋯O3ⁱⁱⁱ	0.93	2.53	3.229 (2)	132
C7—H7B⋯Cg2^iv	0.97	2.57	3.464 (3)	153

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (NNSF; No. 31172365; 31101469).

supplementary crystallographic information

Comment

The allocryptopine derivatives have recently attracted great attention due to their antifungal activity (Morteza et al. 2003), antibacterial activity (Yan et al. 2009), analgesic effect (Capasso et al. 1997), anti-dementia (Jeong et al. 2009; Zhao et al. 2008), and so on. With the interests in the synthesis of allocryptopine derivatives with biological activity, we report here the synthesis and crystal structure of the title compound, (I).

As shown in Fig. 1, the molecule of the title compound is characterized by the presence of a ten-membered ring (hexahydrodibenzo[c,g]azecine) with a methylated tertiary nitrogen atom and a hydroxyl group fused to two aryl moieties. In general, the title compound have two oxygenated substituents on the benzene ring and two methoxyl on the other benzene ring. Benzene rings C1/C2/C3/C4/C5/C6 and C10/C11/C16/C17/C18/C19 are inclined with respect to one another with a dihedral angle of 23.16 (5)°.

In the crystal structure, two adjacent molecules are linked by weak intermolecular O—H···O or C—H···O hydrogen bond into a one-dimension chain along b axis. These chains are further connected by C—H···π interaction into two-dimension sheets.

Experimental

The title compound was synthesized according to the literature procedure (Wada et al. 2007), and colourless blocks of (I) were obtained from a solution in methanol by slow evaporation at room temperature.