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Volume 69 
Part 8 
Pages o1351-o1352  
August 2013  

Received 20 July 2013
Accepted 23 July 2013
Online 31 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.048
wR = 0.134
Data-to-parameter ratio = 25.4
Details
Open access

Bruceolline J: 2-hydroxy-3,3-dimethyl-2,3-dihydrocyclopenta[b]indol-1(4H)-one

aDepartment of Chemistry, Dartmouth College, Hanover, NH 03755-3564, USA, and bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

The 12-membered cyclopenta[b]indole ring system in the title compound, C13H13NO2, deviates only slightly from planarity (r.m.s. deviation = 0.051 Å). In the crystal, N-H...O and O-H...O hydrogen bonds link the molecules into sheets parallel to (100). The five-membered cyclopentanone ring is in slightly distorted envelope conformation with the C atom bearing the hydroxy substituent as the flap.

Related literature

For a review of compounds isolated from Brucea sp. plants, see: Liu et al. (2009[Liu, J.-H., Jin, H.-Z., Zhang, W.-D., Yan, S.-K. & Shen, Y.-H. (2009). Chem. Biodivers. 6, 57-70.]). For the first isolation of bruceolline J, see: Chen et al. (2011[Chen, H., Bai, J., Fang, Z.-F., Yu, S.-S., Ma, S.-G., Xu, S., Li, Y., Qu, J., Ren, J.-H., Li, L., Si, Y.-K. & Chen, X.-G. (2011). J. Nat. Prod. 74, 2438-244.]). For the DDQ-mediated selective oxidation of indole side chains, see: Oikawa & Yonemitsu (1977[Oikawa, Y. & Yonemitsu, O. (1977). J. Org. Chem. 42, 1213-1216.]). For examples of the reduction of [alpha]-keto esters with sodium borohydride, see Dalla et al. (1999[Dalla, V., Catteau, J. P. & Pale, P. (1999). Tetrahedron Lett. 40, 5193-5196.]). For the enantioselective reduction of related sterically hindered ketones with [beta]-chlorodiisopinocampheylborane, see: Brown et al. (1986[Brown, H. C., Chandrasekharan, J. & Ramachandran, P. V. (1986). J. Org. Chem. 51, 3396-3398.]). For the isolation of related bruceollines, see: Ouyang et al. (1994a[Ouyang, Y., Koike, K. & Ohmoto, T. (1994a). Phytochemistry, 36, 1543-1546.],b[Ouyang, Y., Koike, K. & Ohmoto, T. (1994b). Phytochemistry, 37, 575-578.], 1995[Ouyang, Y., Mitsunaga, K., Koike, K. & Ohmoto, T. (1995). Phytochemistry, 39, 911-913.]). For the crystal structure of bruceolline D, see: Lopchuk et al. (2013[Lopchuk, J. M., Gribble, G. W. & Jasinski, J. P. (2013). Acta Cryst. E69, o1043.]). For the total synthesis and crystal structure of bruceolline E, see: Jordan et al. (2011[Jordan, J. A., Gribble, G. W. & Badenock, J. C. (2011). Tetrahedron Lett. 52, 6772-6774.], 2012)[Jordon, J. A., Badenock, J. C., Gribble, G. W., Jasinski, J. P. & Golen, J. A. (2012). Acta Cryst. E68, o364-o365.]. For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13NO2

  • Mr = 215.24

  • Monoclinic, P 21 /c

  • a = 8.2951 (3) Å

  • b = 12.3070 (4) Å

  • c = 10.7340 (4) Å

  • [beta] = 97.207 (3)°

  • V = 1087.15 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 0.44 × 0.38 × 0.34 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.782, Tmax = 1.000

  • 13545 measured reflections

  • 3753 independent reflections

  • 2888 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.134

  • S = 1.04

  • 3753 reflections

  • 148 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...O1i 0.84 1.90 2.7245 (12) 168
N1-H1...O2ii 0.88 1.91 2.7500 (12) 158
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: XP in SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6922 ).


Acknowledgements

JML acknowledges support from a Graduate Assistance in Areas of National Need (GAANN) fellowship. GWG acknowledges support by the Donors of the Petroleum Research Fund (PRF), administered by the American Chemical Society, and by Wyeth. JPJ acknowledges the NSF MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Brown, H. C., Chandrasekharan, J. & Ramachandran, P. V. (1986). J. Org. Chem. 51, 3396-3398.  [CrossRef] [ChemPort]
Chen, H., Bai, J., Fang, Z.-F., Yu, S.-S., Ma, S.-G., Xu, S., Li, Y., Qu, J., Ren, J.-H., Li, L., Si, Y.-K. & Chen, X.-G. (2011). J. Nat. Prod. 74, 2438-244.  [CrossRef] [ChemPort] [PubMed]
Dalla, V., Catteau, J. P. & Pale, P. (1999). Tetrahedron Lett. 40, 5193-5196.  [CrossRef] [ChemPort]
Jordan, J. A., Gribble, G. W. & Badenock, J. C. (2011). Tetrahedron Lett. 52, 6772-6774.  [Web of Science] [CrossRef] [ChemPort]
Jordon, J. A., Badenock, J. C., Gribble, G. W., Jasinski, J. P. & Golen, J. A. (2012). Acta Cryst. E68, o364-o365.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Liu, J.-H., Jin, H.-Z., Zhang, W.-D., Yan, S.-K. & Shen, Y.-H. (2009). Chem. Biodivers. 6, 57-70.  [CrossRef] [PubMed] [ChemPort]
Lopchuk, J. M., Gribble, G. W. & Jasinski, J. P. (2013). Acta Cryst. E69, o1043.  [CrossRef] [IUCr Journals]
Oikawa, Y. & Yonemitsu, O. (1977). J. Org. Chem. 42, 1213-1216.  [CrossRef] [ChemPort]
Ouyang, Y., Koike, K. & Ohmoto, T. (1994a). Phytochemistry, 36, 1543-1546.  [CrossRef] [ChemPort] [PubMed]
Ouyang, Y., Koike, K. & Ohmoto, T. (1994b). Phytochemistry, 37, 575-578.  [ChemPort]
Ouyang, Y., Mitsunaga, K., Koike, K. & Ohmoto, T. (1995). Phytochemistry, 39, 911-913.  [CrossRef] [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1351-o1352   [ doi:10.1107/S1600536813020527 ]

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