Document Detail

3'-(3-Hy-droxy-phen-yl)-4-methyl-spiro-[benzo[e][1,4]diazepine-3,2'-oxirane]-2,5(1H,4H)-dione.
Jump to Full Text
MedLine Citation:
PMID:  21837069     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
In the title compound, C(17)H(14)N(2)O(4), 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 inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.
Authors:
Jun-Liang Liu; Zhi-Yu Hu; Qing-Yan Xu
Related Documents :
22259509 - 3-methyl-anilinium hydrogen phthalate.
21429689 - In vitro photobiochemical characterization of sulfobutylether-β-cyclodextrin formulati...
21589439 - 3-diethyl-amino-6-[(z)-(4-hy-droxy-anilino)methyl-idene]cyclo-hexa-2,4-dienone.
21581719 - 4-chloro-3-nitro-benzamide.
21401049 - Thermal decomposition of 2-butanol as a potential nonfossil fuel: a computational study.
21141869 - Ultra-sensitive fluorescent sensor for hg2+ based on a donor-acceptor-donor framework.
21939659 - Essential role of the metal ion in the ipm-assisted domain closure of 3-isopropylmalate...
18964339 - 2,6-diacetylpyridine bis(arylhydrazone) derivatives as analytical reagents for uranium.
23580169 - A xas study of the luminescent eu centers in thiosilicate phosphors.
Publication Detail:
Type:  Journal Article     Date:  2011-06-18
Journal Detail:
Title:  Acta crystallographica. Section E, Structure reports online     Volume:  67     ISSN:  1600-5368     ISO Abbreviation:  Acta Crystallogr Sect E Struct Rep Online     Publication Date:  2011 Jul 
Date Detail:
Created Date:  2011-08-12     Completed Date:  2011-11-10     Revised Date:  2011-12-09    
Medline Journal Info:
Nlm Unique ID:  101089178     Medline TA:  Acta Crystallogr Sect E Struct Rep Online     Country:  England    
Other Details:
Languages:  eng     Pagination:  o1670     Citation Subset:  -    
Affiliation:
Laboratory of Microbial Pharmaceutical Engineering, School of Life Sciences, Xiamen University, Xiamen 361005, People's Republic of China.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Full Text
Journal Information
Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online
Journal ID (publisher-id): Acta Cryst. E
ISSN: 1600-5368
Publisher: International Union of Crystallography
Article Information
Download PDF
A full version of this article is available from Crystallography Journals Online.© Liu et al. 2011
open-access:
Received Day: 31 Month: 5 Year: 2011
Accepted Day: 08 Month: 6 Year: 2011
collection publication date: Day: 01 Month: 7 Year: 2011
Electronic publication date: Day: 18 Month: 6 Year: 2011
pmc-release publication date: Day: 18 Month: 6 Year: 2011
Volume: 67 Issue: Pt 7
First Page: o1670 Last Page: o1670
ID: 3152106
PubMed Id: 21837069
Publisher Id: xu5236
DOI: 10.1107/S1600536811022161
Coden: ACSEBH
Publisher Item Identifier: S1600536811022161

3′-(3-Hy­droxy­phen­yl)-4-methyl­spiro­[benzo[e][1,4]diazepine-3,2′-oxirane]-2,5(1H,4H)-dione Alternate Title:C17H14N2O4
Jun-Liang Liua
Zhi-Yu Hua
Qing-Yan Xua*
aLaboratory of Microbial Pharmaceutical Engineering, School of Life Sciences, Xiamen University, Xiamen 361005, People’s Republic of China
Correspondence: Correspondence e-mail: xuqingyan@xmu.edu.cn

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).[Chemical Structure ID: scheme1]


Experimental
Crystal data

  • C17H14N2O4
  • Mr = 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)
  • Rint = 0.021

Refinement

  • R[F2 > 2σ(F2)] = 0.033
  • wR(F2) = 0.107
  • S = 0.99
  • 1701 reflections
  • 208 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −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

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

Supplementary material file. DOI: 10.1107/S1600536811022161/xu5236Isup3.cml

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


Notes

fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5236).

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%).

Refinement

H atoms were positioned geometrically and were treated as riding on their parent atoms, with C—H distances of 0.93–0.98 Å, an N—H distance of 0.86 Å, and O—H distance of 0.82Å and Uiso(H)=1.2Ueq(N,C).

Figures
Crystal data
Data collection
Refinement
Special details
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, °)
Hydrogen-bond geometry (Å, °)

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z.


References
Birkinshaw, J. H., Luckner, M., Mohammed, Y. S., Mothes, K. & Stickings, C. E. (1963). Biochem. J.89, 196–202.
Bruker (2007). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
Cutler, H. G., Crumley, F. G., Cox, R. H., Wells, J. & Cole, R. J. (1984). Plant Cell Physiol25, 257–263.
Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
Heguy, A., Cai, P., Meyn, P., Houck, D., Russo, S., Michitsch, R., Pearce, C. & Katz, B. (1998). Antivir. Chem. Chemother.9, 149–155.
Nover, L. & Luckner, M. (1969). Eur. J. Biochem.10, 268–273.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Figures

[Figure ID: Fap1]
Fig. 1. 

The molecular structure of the title compound with 50% probability ellipsoids.



[Figure ID: Fap2]
Fig. 2. 

Partial packing diagram of the title compound, viewed along the a axis.



Tables
[TableWrap ID: d1e128]
C17H14N2O4 F(000) = 324
Mr = 310.30 Dx = 1.455 Mg m3
Monoclinic, P21 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb Cell parameters from 1484 reflections
a = 7.0066 (2) Å θ = 1.9–27.5°
b = 11.6160 (4) Å µ = 0.11 mm1
c = 9.1568 (2) Å T = 193 K
β = 108.157 (1)° Block, colourless
V = 708.15 (4) Å3 0.55 × 0.32 × 0.22 mm
Z = 2

[TableWrap ID: d1e255]
Bruker SMART 1000 CCD area-detector diffractometer 1627 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.021
graphite θmax = 27.5°, θmin = 3.1°
φ and ω scans h = −8→9
6890 measured reflections k = −15→15
1701 independent reflections l = −11→11

[TableWrap ID: d1e353]
Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107 H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
1701 reflections (Δ/σ)max = 0.009
208 parameters Δρmax = 0.21 e Å3
1 restraint Δρmin = −0.24 e Å3

[TableWrap ID: d1e507]
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

[TableWrap ID: d1e606]
x y z Uiso*/Ueq
O2 0.4377 (2) 0.08072 (14) 0.31423 (17) 0.0269 (3)
O3 0.4521 (2) 0.40192 (14) 0.02123 (17) 0.0227 (3)
O1 0.6694 (2) 0.51497 (15) 0.29249 (19) 0.0291 (4)
O4 −0.0361 (2) 0.06229 (14) −0.25108 (18) 0.0271 (4)
H4A 0.0758 0.0542 −0.2604 0.041*
N2 0.4837 (2) 0.24388 (15) 0.19567 (18) 0.0184 (3)
N1 0.4887 (2) 0.42631 (15) 0.42617 (18) 0.0205 (4)
H1 0.5578 0.4610 0.5087 0.025*
C8 0.3244 (3) 0.35791 (17) 0.4353 (2) 0.0186 (4)
C9 0.2804 (3) 0.24831 (18) 0.3691 (2) 0.0186 (4)
C7 0.2100 (3) 0.40240 (19) 0.5227 (2) 0.0216 (4)
H7 0.2433 0.4733 0.5712 0.026*
C4 0.1162 (3) 0.18798 (19) 0.3878 (2) 0.0236 (4)
H4 0.0858 0.1152 0.3445 0.028*
C3 0.4063 (3) 0.18510 (18) 0.2913 (2) 0.0192 (4)
C12 0.1144 (3) 0.22949 (19) −0.1034 (2) 0.0212 (4)
H12 0.2423 0.1976 −0.0787 0.025*
C10 0.6209 (3) 0.1863 (2) 0.1253 (2) 0.0257 (4)
H10A 0.6350 0.1068 0.1554 0.038*
H10B 0.7499 0.2231 0.1592 0.038*
H10C 0.5671 0.1915 0.0154 0.038*
C16 −0.1031 (3) 0.3876 (2) −0.0884 (2) 0.0241 (4)
H16 −0.1207 0.4607 −0.0531 0.029*
C11 0.0875 (3) 0.33865 (18) −0.0492 (2) 0.0201 (4)
C14 −0.2433 (3) 0.21769 (19) −0.2334 (2) 0.0234 (4)
H14 −0.3541 0.1771 −0.2941 0.028*
C6 0.0469 (3) 0.3415 (2) 0.5378 (2) 0.0247 (4)
H6 −0.0307 0.3725 0.5941 0.030*
C13 −0.0508 (3) 0.16860 (19) −0.1948 (2) 0.0208 (4)
C17 0.2579 (3) 0.40891 (18) 0.0485 (2) 0.0198 (4)
H17 0.2200 0.4869 0.0695 0.024*
C15 −0.2672 (3) 0.3264 (2) −0.1808 (2) 0.0252 (4)
H15 −0.3946 0.3592 −0.2075 0.030*
C2 0.4422 (3) 0.36451 (16) 0.1645 (2) 0.0180 (4)
C5 −0.0007 (3) 0.2341 (2) 0.4688 (2) 0.0267 (5)
H5 −0.1113 0.1937 0.4774 0.032*
C1 0.5463 (3) 0.44186 (18) 0.2995 (2) 0.0195 (4)

[TableWrap ID: d1e1135]
U11 U22 U33 U12 U13 U23
O2 0.0382 (8) 0.0157 (7) 0.0268 (7) 0.0038 (6) 0.0100 (6) 0.0041 (6)
O3 0.0288 (7) 0.0214 (7) 0.0222 (7) 0.0002 (5) 0.0139 (5) 0.0024 (6)
O1 0.0309 (8) 0.0236 (8) 0.0359 (8) −0.0097 (6) 0.0149 (6) −0.0027 (7)
O4 0.0268 (7) 0.0222 (8) 0.0341 (8) −0.0028 (6) 0.0121 (6) −0.0060 (6)
N2 0.0227 (7) 0.0155 (8) 0.0180 (7) 0.0029 (6) 0.0077 (6) 0.0006 (7)
N1 0.0236 (8) 0.0174 (8) 0.0189 (8) −0.0052 (6) 0.0044 (6) −0.0034 (6)
C8 0.0194 (9) 0.0184 (9) 0.0169 (8) −0.0022 (7) 0.0042 (7) 0.0015 (7)
C9 0.0225 (8) 0.0181 (9) 0.0144 (8) 0.0006 (7) 0.0046 (7) 0.0022 (7)
C7 0.0273 (9) 0.0183 (9) 0.0180 (8) 0.0001 (7) 0.0052 (7) −0.0012 (7)
C4 0.0251 (9) 0.0204 (10) 0.0234 (9) −0.0063 (8) 0.0050 (7) 0.0004 (8)
C3 0.0220 (9) 0.0140 (9) 0.0188 (8) 0.0025 (7) 0.0021 (6) 0.0016 (7)
C12 0.0234 (9) 0.0216 (10) 0.0186 (8) 0.0041 (7) 0.0065 (7) 0.0022 (7)
C10 0.0248 (10) 0.0251 (11) 0.0290 (9) 0.0094 (8) 0.0113 (7) −0.0007 (8)
C16 0.0289 (10) 0.0229 (10) 0.0216 (9) 0.0058 (8) 0.0096 (8) 0.0013 (8)
C11 0.0256 (9) 0.0208 (10) 0.0149 (8) 0.0012 (7) 0.0076 (7) 0.0007 (7)
C14 0.0204 (9) 0.0291 (12) 0.0213 (9) −0.0014 (7) 0.0071 (7) 0.0018 (8)
C6 0.0277 (10) 0.0291 (11) 0.0202 (9) 0.0014 (8) 0.0117 (8) 0.0027 (8)
C13 0.0265 (9) 0.0187 (9) 0.0195 (8) −0.0010 (8) 0.0105 (7) 0.0000 (7)
C17 0.0263 (10) 0.0163 (9) 0.0178 (8) 0.0017 (7) 0.0085 (7) 0.0028 (7)
C15 0.0234 (10) 0.0300 (12) 0.0230 (10) 0.0054 (8) 0.0082 (8) 0.0030 (8)
C2 0.0220 (9) 0.0143 (9) 0.0193 (8) 0.0005 (7) 0.0087 (7) 0.0016 (7)
C5 0.0263 (10) 0.0300 (12) 0.0252 (10) −0.0084 (9) 0.0101 (8) 0.0025 (9)
C1 0.0200 (8) 0.0149 (9) 0.0238 (9) 0.0001 (6) 0.0069 (7) −0.0002 (7)

[TableWrap ID: d1e1555]
O2—C3 1.238 (3) C12—C13 1.392 (3)
O3—C2 1.405 (2) C12—C11 1.396 (3)
O3—C17 1.461 (2) C12—H12 0.9300
O1—C1 1.226 (3) C10—H10A 0.9600
O4—C13 1.354 (3) C10—H10B 0.9600
O4—H4A 0.8200 C10—H10C 0.9600
N2—C3 1.350 (3) C16—C15 1.392 (3)
N2—C2 1.441 (2) C16—C11 1.392 (3)
N2—C10 1.474 (2) C16—H16 0.9300
N1—C1 1.354 (3) C11—C17 1.492 (3)
N1—C8 1.422 (2) C14—C15 1.380 (3)
N1—H1 0.8600 C14—C13 1.404 (3)
C8—C7 1.397 (3) C14—H14 0.9300
C8—C9 1.402 (3) C6—C5 1.391 (3)
C9—C4 1.403 (3) C6—H6 0.9300
C9—C3 1.489 (3) C17—C2 1.486 (3)
C7—C6 1.387 (3) C17—H17 0.9800
C7—H7 0.9300 C15—H15 0.9300
C4—C5 1.373 (3) C2—C1 1.518 (3)
C4—H4 0.9300 C5—H5 0.9300
C2—O3—C17 62.43 (12) C11—C16—H16 120.2
C13—O4—H4A 109.5 C16—C11—C12 120.29 (19)
C3—N2—C2 121.51 (17) C16—C11—C17 117.10 (18)
C3—N2—C10 120.16 (17) C12—C11—C17 122.59 (17)
C2—N2—C10 118.28 (17) C15—C14—C13 119.7 (2)
C1—N1—C8 125.99 (16) C15—C14—H14 120.1
C1—N1—H1 117.0 C13—C14—H14 120.1
C8—N1—H1 117.0 C7—C6—C5 119.99 (19)
C7—C8—C9 119.68 (18) C7—C6—H6 120.0
C7—C8—N1 116.53 (18) C5—C6—H6 120.0
C9—C8—N1 123.70 (17) O4—C13—C12 122.98 (18)
C4—C9—C8 118.62 (18) O4—C13—C14 117.11 (18)
C4—C9—C3 116.31 (19) C12—C13—C14 119.9 (2)
C8—C9—C3 124.83 (17) O3—C17—C2 56.95 (11)
C6—C7—C8 120.4 (2) O3—C17—C11 118.78 (16)
C6—C7—H7 119.8 C2—C17—C11 126.41 (18)
C8—C7—H7 119.8 O3—C17—H17 114.1
C5—C4—C9 121.4 (2) C2—C17—H17 114.1
C5—C4—H4 119.3 C11—C17—H17 114.1
C9—C4—H4 119.3 C14—C15—C16 120.80 (18)
O2—C3—N2 121.27 (19) C14—C15—H15 119.6
O2—C3—C9 120.14 (19) C16—C15—H15 119.6
N2—C3—C9 118.58 (18) O3—C2—N2 114.81 (16)
C13—C12—C11 119.76 (18) O3—C2—C17 60.63 (12)
C13—C12—H12 120.1 N2—C2—C17 123.77 (17)
C11—C12—H12 120.1 O3—C2—C1 115.22 (16)
N2—C10—H10A 109.5 N2—C2—C1 113.46 (16)
N2—C10—H10B 109.5 C17—C2—C1 117.85 (17)
H10A—C10—H10B 109.5 C4—C5—C6 119.79 (19)
N2—C10—H10C 109.5 C4—C5—H5 120.1
H10A—C10—H10C 109.5 C6—C5—H5 120.1
H10B—C10—H10C 109.5 O1—C1—N1 122.65 (19)
C15—C16—C11 119.5 (2) O1—C1—C2 122.34 (19)
C15—C16—H16 120.2 N1—C1—C2 114.97 (17)

[TableWrap ID: d1e2067]
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


Article Categories:
  • Organic Papers


Previous Document:  Bis[(1-methyl-1H-tetra-zol-5-yl)sulfan-yl]ethane.
Next Document:  [(5-Bromo-1H-indol-3-yl)meth-yl]dimethyl-aza-nium nitrate.