3′-(3-Hy­droxy­phen­yl)-4-methyl­spiro­[benzo[e][1,4]diazepine-3,2′-oxirane]-2,5(1H,4H)-dione

Jun-Liang Liu; Zhi-Yu Hu; Qing-Yan Xu

doi:10.1107/S1600536811022161

. 2011 Jun 18;67(Pt 7):o1670. doi: 10.1107/S1600536811022161

3′-(3-Hydroxyphenyl)-4-methylspiro[benzo[e][1,4]diazepine-3,2′-oxirane]-2,5(1H,4H)-dione

Jun-Liang Liu ^a, Zhi-Yu Hu ^a, Qing-Yan Xu ^a,^*

PMCID: PMC3152106 PMID: 21837069

Abstract

In the title compound, C₁₇H₁₄N₂O₄, the seven-membered ring adopts a boat conformation, and the two benzene rings make a dihedral angle of 45.22 (5)°. The crystal packing is stabilized by intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the biological activity of the title compound, see: Birkinshaw et al. (1963 ▶); Cutler et al. (1984 ▶); Heguy, et al. (1998 ▶). For the biosynthesis of cyclopenol, see: Nover & Luckner (1969 ▶).

Experimental

Crystal data

C₁₇H₁₄N₂O₄
M _r = 310.30
Monoclinic,
a = 7.0066 (2) Å
b = 11.6160 (4) Å
c = 9.1568 (2) Å
β = 108.157 (1)°
V = 708.15 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 193 K
0.55 × 0.32 × 0.22 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
6890 measured reflections
1701 independent reflections
1627 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.107
S = 0.99
1701 reflections
208 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811022161/xu5236sup1.cif

e-67-o1670-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022161/xu5236Isup2.hkl

e-67-o1670-Isup2.hkl^{(83.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811022161/xu5236Isup3.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
N1—H1⋯O2ⁱ	0.86	2.13	2.893 (2)	148
O4—H4A⋯O1ⁱⁱ	0.82	1.95	2.7689 (17)	173

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

Acknowledgments

The authors thank the Fundamental Research Funds for the Central Universities, China, for financial support (grant No. 2010121092).

supplementary crystallographic information

Comment

The title compund named cyclopenol is an benzodiazepine metabolite produced by a number of Penicllium species. Cyclopenol isolated from Penicillium cyclopium Westling (Birkinshaw et al., 1963). It display intermediate in the biosynthesis of viridicatins, inhibitors of the TNF-α-induced replication of human HIV (Nover & Luckner, 1969; Heguy, et al., 1998). It is of ecological significance due to its phytotoxic and antimicrobial properties (Cutler, et al., 1984). In our study, we determined the crystal structure of the title compound. The seven membered ring adopts a boat conformation. The crystal packing is stabilized by intermolecular N—H···O and O—H···O hydrogen bondings (Table 1).

Experimental

The fungal F00734 was cultured using half sea-water Potato Dextrose Agar medium at 28 degrees celsius for 14 days. The fermentation (10 liters) was extracted with ethyl acetate (EtOAc). The EtOAc extract (5.0 g) which was subjected to column chromatography over RP-18, eluted with Methanol-H₂O (30%, 50%, 70%, 100%; V/V) to yield 10 fractions. Fraction 5, eluted with methanol was further puried by Sephadex LH-20 chromatography. Then merged the components 1–15 tubes eluted with acetone, and further purified by silica-gel column chromatography to afford the title compound 1 (140.0 mg). F00734 is an high-yield strain of cyclopenol (2.8%).