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Volume 69 
Part 6 
Pages o924-o925  
June 2013  

Received 30 April 2013
Accepted 10 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 102 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.114
Data-to-parameter ratio = 14.0
Details
Open access

3,4-Bis[1-(prop-2-ynyl)-1H-indol-3-yl]-1H-pyrrole-2,5-dione

aSchool of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, People's Republic of China, and bDepartment of Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China
Correspondence e-mail: mhhuang@bit.edu.cn

In the title molecule, C26H17N3O2, both indole ring systems are essentially planar, with maximum deviations of 0.019 (2) and 0.033 (1) Å for the N atoms, and form dihedral angles of 34.40 (9) and 45.06 (8)° with the essentially planar pyrrole ring [maximum deviation = 0.020 (2) Å]. The dihedral angle between the two indole ring systems is 58.78 (6)°. In the crystal, molecules are connected by pairs of N-H...O hydrogen bonds, forming inversion dimers and generating R22(8) rings. Weak [pi]-[pi] stacking interactions, with a centroid-centroid distance of 3.983 (2) Å, are also observed.

Related literature

For the importance of bisindolylmaleimides in medicinal chemistry, see: Bulbule et al. (2008[Bulbule, V. J., Rivas, K., Verlinde, C. L. M. J., Van Voorhis, W. C. & Gelb, M. H. (2008). J. Med. Chem. 51, 384-387.]); Wang et al. (2012[Wang, K., Yan, Z., Wang, N. & Liu, Z. Z. (2012). Chin. Chem. Lett. 23, 462-465.]) and in materials science, see: Chiu et al. (2003[Chiu, C.-W., Chow, T.-J., Chuen, C.-H., Lin, H.-M. & Tao, Y.-T. (2003). Chem. Mater. 15, 4527-4532.]); Kaletas et al. (2005[Kaletas, B. K., Kozhevnikov, V. N., Zimine, M., Williams, R. M., Koenig, B. & De Cola, L. (2005). Eur. J. Org. Chem. pp. 3443-3449.]); Lin et al. (2010[Lin, Z., Lin, Y.-D., Wu, C.-Y., Chow, P.-T., Sun, C.-H. & Chow, T. J. (2010). Macromolecules, 43, 5925-5931.]); Nakazono et al. (2007[Nakazono, M., Nanbu, S., Uesaki, A., Kuwano, R., Kashiwabara, M. & Zaitsu, K. (2007). Org. Lett. 9, 3583-3586.]); Yeh et al. (2006[Yeh, T.-S., Chow, T. J., Tsai, S.-H., Chiu, C.-W. & Zhao, C.-X. (2006). Chem. Mater. 18, 832-839.]). For the isolation of bisindolylmaleimides from natural products, see: Kamata et al. (2006[Kamata, K., Suetsugu, T., Yamamoto, Y., Hayashi, M., Komiyama, K. & Ishibashi, M. (2006). J. Nat. Prod. 69, 1252-1254.]). For the synthesis of bisindolylmaleimides, see: Prateeptongkum et al. (2010[Prateeptongkum, S., Driller, K. M., Jackstell, R., Spannenberg, A. & Beller, M. (2010). Chem. Eur. J. 16, 9606-9615.]). For a related crystal structure, see: Huang et al. (2012[Huang, L., Li, Y., Gao, D. & Du, Z. (2012). Acta Cryst. E68, o1328.]). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C26H17N3O2

  • Mr = 403.43

  • Triclinic, [P \overline 1]

  • a = 8.8015 (14) Å

  • b = 11.2619 (14) Å

  • c = 11.838 (3) Å

  • [alpha] = 62.860 (17)°

  • [beta] = 73.625 (16)°

  • [gamma] = 79.593 (12)°

  • V = 999.9 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 102 K

  • 0.11 × 0.10 × 0.07 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.991, Tmax = 0.994

  • 6379 measured reflections

  • 3920 independent reflections

  • 3113 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.114

  • S = 1.03

  • 3920 reflections

  • 280 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.88 2.01 2.872 (2) 165
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5613 ).


Acknowledgements

The authors wish to thank the Natural Science Foundation of China (No. 21202008) for generous support.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brandenburg, K. (2006). DIAMOND. Crystal Impact, Bonn, Germany.
Bruker (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bulbule, V. J., Rivas, K., Verlinde, C. L. M. J., Van Voorhis, W. C. & Gelb, M. H. (2008). J. Med. Chem. 51, 384-387.  [ISI] [CrossRef] [PubMed] [ChemPort]
Chiu, C.-W., Chow, T.-J., Chuen, C.-H., Lin, H.-M. & Tao, Y.-T. (2003). Chem. Mater. 15, 4527-4532.  [ISI] [CSD] [CrossRef] [ChemPort]
Huang, L., Li, Y., Gao, D. & Du, Z. (2012). Acta Cryst. E68, o1328.  [CSD] [CrossRef] [details]
Kaletas, B. K., Kozhevnikov, V. N., Zimine, M., Williams, R. M., Koenig, B. & De Cola, L. (2005). Eur. J. Org. Chem. pp. 3443-3449.
Kamata, K., Suetsugu, T., Yamamoto, Y., Hayashi, M., Komiyama, K. & Ishibashi, M. (2006). J. Nat. Prod. 69, 1252-1254.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lin, Z., Lin, Y.-D., Wu, C.-Y., Chow, P.-T., Sun, C.-H. & Chow, T. J. (2010). Macromolecules, 43, 5925-5931.  [ISI] [CrossRef] [ChemPort]
Nakazono, M., Nanbu, S., Uesaki, A., Kuwano, R., Kashiwabara, M. & Zaitsu, K. (2007). Org. Lett. 9, 3583-3586.  [ISI] [CrossRef] [PubMed] [ChemPort]
Prateeptongkum, S., Driller, K. M., Jackstell, R., Spannenberg, A. & Beller, M. (2010). Chem. Eur. J. 16, 9606-9615.  [CSD] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wang, K., Yan, Z., Wang, N. & Liu, Z. Z. (2012). Chin. Chem. Lett. 23, 462-465.  [CrossRef] [ChemPort]
Yeh, T.-S., Chow, T. J., Tsai, S.-H., Chiu, C.-W. & Zhao, C.-X. (2006). Chem. Mater. 18, 832-839.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o924-o925   [ doi:10.1107/S1600536813012889 ]

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