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Volume 69 
Part 6 
Page o929  
June 2013  

Received 19 April 2013
Accepted 15 May 2013
Online 22 May 2013

Key indicators
Single-crystal X-ray study
T = 143 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.112
Data-to-parameter ratio = 15.0
Details
Open access

6-Amino-2-methyl-8-phenyl-1,2,3,4-tetrahydroisoquinoline-5,7-dicarbonitrile

aDepartment of Pharmaceutical and Biological Engineering, College of Chemical Engineering, Sichuan University, Chengdu 610065, People's Republic of China
Correspondence e-mail: cusack@scu.edu.cn

In the title compound, C18H16N4, the dihedral angle between the benzene and phenyl rings is 61.40 (4)°. In the crystal, molecules are linked by N-H...N(nitrile) hydrogen bonds, forming inversion dimers. The dimers are further linked by N-H...N(amine) hydrogen bonds, and both units are arranged almost perpendicular to each other [angle between dimer mean planes = 84.43 (12)°]. This arrangement is extended to form a ladder-like structure parallel to the c axis.

Related literature

For background to natural products containing an isoquinoline backbone, see: Marchand et al. (2006[Marchand, C., Antony, S., Kohn, K. W., Cushman, M., Ioanoviciu, A., Staker, B. L., Burgin, A. B., Stewart, L. & Pommier, Y. (2006). Mol. Cancer Ther. 5, 287-295.]); Cho et al. (2007[Cho, W.-J., Le, Q. M., Van, H. T. M., Lee, K. Y., Kang, B. Y., Lee, E.-S., Lee, S. K. & Kwon, Y. (2007). Bioorg. Med. Chem. Lett. 17, 3531-3534.]); Van Quaquebeke et al. (2007[Van Quaquebeke, E., Mahieu, T., Dumont, P., Dewelle, J., Ribaucour, F., Simon, G., Sauvage, S., Gaussin, J.-F., Tuti, J., El Yazidi, M., Van Vynckt, F., Mijatovic, T., Lefranc, F., Darro, F. & Kiss, R. (2007). J. Med. Chem. 50, 4122-4134.]). For related structures, see: Rong et al. (2010[Rong, L. C., Gao, L. J., Han, H. X., Jiang, H., Dai, Y. S. & Tu, S. J. (2010). Synth. Commun. 40, 289-294.]); Balamurugan et al. (2011[Balamurugan, K., Jeyachandran, V., Perumal, S. & Menéndez, J. C. (2011). Tetrahedron, 67, 1432-1437.]).

[Scheme 1]

Experimental

Crystal data
  • C18H16N4

  • Mr = 288.35

  • Monoclinic, P 21 /c

  • a = 17.5630 (5) Å

  • b = 6.25208 (19) Å

  • c = 13.7963 (4) Å

  • [beta] = 93.209 (3)°

  • V = 1512.53 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 143 K

  • 0.38 × 0.35 × 0.25 mm

Data collection
  • Agilent Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction, Yarnton, England.]) Tmin = 0.960, Tmax = 1.000

  • 6799 measured reflections

  • 3089 independent reflections

  • 2414 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.112

  • S = 1.05

  • 3089 reflections

  • 206 parameters

  • 4 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4A...N2i 0.89 (1) 2.21 (1) 3.052 (2) 157 (2)
N4-H4B...N1ii 0.87 (1) 2.21 (1) 3.0261 (19) 155 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: 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.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2477 ).


Acknowledgements

We thank the Analytical and Testing Center of Sichuan University for the X-ray measurements.

References

Balamurugan, K., Jeyachandran, V., Perumal, S. & Menéndez, J. C. (2011). Tetrahedron, 67, 1432-1437.  [ISI] [CSD] [CrossRef] [ChemPort]
Cho, W.-J., Le, Q. M., Van, H. T. M., Lee, K. Y., Kang, B. Y., Lee, E.-S., Lee, S. K. & Kwon, Y. (2007). Bioorg. Med. Chem. Lett. 17, 3531-3534.  [CrossRef] [PubMed] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Marchand, C., Antony, S., Kohn, K. W., Cushman, M., Ioanoviciu, A., Staker, B. L., Burgin, A. B., Stewart, L. & Pommier, Y. (2006). Mol. Cancer Ther. 5, 287-295.  [ISI] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction, Yarnton, England.
Rong, L. C., Gao, L. J., Han, H. X., Jiang, H., Dai, Y. S. & Tu, S. J. (2010). Synth. Commun. 40, 289-294.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Van Quaquebeke, E., Mahieu, T., Dumont, P., Dewelle, J., Ribaucour, F., Simon, G., Sauvage, S., Gaussin, J.-F., Tuti, J., El Yazidi, M., Van Vynckt, F., Mijatovic, T., Lefranc, F., Darro, F. & Kiss, R. (2007). J. Med. Chem. 50, 4122-4134.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o929  [ doi:10.1107/S1600536813013342 ]

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