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Volume 69 
Part 7 
Page o1043  
July 2013  

Received 29 May 2013
Accepted 30 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.068
wR = 0.174
Data-to-parameter ratio = 13.9
Details
Open access

Bruceolline D: 3,3-dimethyl-1H,4H-cyclopenta[b]indol-2(3H)-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 title compound, C13H13NO, crystallizes with four independent molecules in the asymmetric unit. The 12-membered penta[b]indole rings are essentially planar, with maximum deviations ranging from 0.034 (4) to 0.036 (4) Å in the four unique molecules. In the crystal, weak C-H...O interactions are observed, which link the molecules into chains along [010].

Related literature

For the first isolation of bruceolline D, see: Ouyang et al. (1994[Ouyang, Y., Koike, K. & Ohmoto, T. (1994). Phytochemistry, 37, 575-578.]). For a Fischer indole synthesis approach to bruceolline D, see: Dashkevich (1978[Dashkevich, S. N. (1978). Chem. Heterocycl. Compd, 14, 109.]). For the methylation of 2-methylcyclopentane-1,3-dione, see: Agosta & Smith (1970[Agosta, W. C. & Smith, A. B. (1970). J. Org. Chem. 35, 3856-3860.]). For the palladium-catalysed synthesis of related fused indole structures, see: Nazare et al. (2004[Nazare, M., Schneider, C., Lindenschmidt, A. & Will, D. W. (2004). Angew. Chem. Int. Ed. 43, 4526-4528.]). For the isolation of related bruceollines, 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, 2438-2445.]). 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 standard bond lengths, 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
  • C13H13NO

  • Mr = 199.24

  • Orthorhombic, P b c 21

  • a = 10.13410 (14) Å

  • b = 21.9219 (3) Å

  • c = 19.3747 (3) Å

  • V = 4304.27 (11) Å3

  • Z = 16

  • Cu K[alpha] radiation

  • [mu] = 0.62 mm-1

  • T = 173 K

  • 0.32 × 0.18 × 0.06 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 = 0.876, Tmax = 1.000

  • 28235 measured reflections

  • 7612 independent reflections

  • 7097 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.068

  • wR(F2) = 0.174

  • S = 1.04

  • 7612 reflections

  • 549 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.69 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9B-H9B...O1Bi 0.95 2.51 3.427 (4) 162
C10B-H10B...O1A 0.95 2.61 3.379 (5) 139
C12B-H12D...O1Cii 0.98 2.73 3.497 (6) 136
C9D-H9D...O1Diii 0.95 2.46 3.372 (4) 161
C10D-H10D...O1Cii 0.95 2.46 3.274 (5) 144
C12D-H12J...O1Aiv 0.98 2.69 3.485 (6) 138
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, z]; (ii) [-x+1, y-{\script{1\over 2}}, z]; (iii) [-x, y-{\script{1\over 2}}, z]; (iv) x-1, y, z.

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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5328 ).


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.
Agosta, W. C. & Smith, A. B. (1970). J. Org. Chem. 35, 3856-3860.  [CrossRef] [ChemPort]
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.
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, 2438-2445.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Dashkevich, S. N. (1978). Chem. Heterocycl. Compd, 14, 109.  [CrossRef]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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]
Jordan, J. A., Gribble, G. W. & Badenock, J. C. (2011). Tetrahedron Lett. 52, 6772-6774.  [Web of Science] [CrossRef] [ChemPort]
Nazare, M., Schneider, C., Lindenschmidt, A. & Will, D. W. (2004). Angew. Chem. Int. Ed. 43, 4526-4528.  [ChemPort]
Ouyang, Y., Koike, K. & Ohmoto, T. (1994). Phytochemistry, 37, 575-578.  [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, o1043  [ doi:10.1107/S1600536813014955 ]

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