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Volume 69 
Part 12 
Pages o1741-o1742  
December 2013  

Received 6 September 2013
Accepted 24 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.115
Data-to-parameter ratio = 14.0
Details
Open access

N-Benzyl-2-hy­droxy­ethanaminium cyanurate

aInstituto de Química, Universidad Nacional Autónoma de México, Circuito exterior, Ciudad Universitaria, México, D.F., 04510, Mexico, and bUniversidad Politécnica de Tlaxcala Km. 9.5 Carretera Federal Tlaxcala-Puebla, Av. Universidad Politécnica No. 1 Xalcaltzingo, Tepeyanco, Tlaxcala, C.P., 90180, Mexico
Correspondence e-mail: ericka.santacruz@uptlax.edu.mx

In the cation of the title compound C9H14ON+·C3H2O3N3-, the benzyl­amine C-N bond subtends a dihedral angle of 78.3 (2)° with the phenyl ring. The cyanurate anion is in the usual keto-form and shows an r.m.s. deviation from planarity of 0.010 Å. In the crystal, the cyanurate anions form N-H...O hydrogen-bonded zigzag ribbons along [001]. These ribbons are crosslinked by the organocations via O-H...N and N-H...O hydrogen bonds, forming bilayers parallel to (010) which are held together along [010] by slipped [pi]-[pi] inter­actions between pairs of cyanurate anions [shortest contact distances C...C = 3.479 (2), O...N = 3.400 (2); centroid-centroid distance= 4.5946 (9) Å] and between cyanurate and phenyl rings [centroid-centroid distance = 3.7924 (12) Å, ring-ring angle = 11.99 (10)°].

Related literature

For adducts of cyanuric acid, see: Sivashankar (2000[Sivashankar, K. (2000). Proc. Indian Acad. Sci. Chem. Sci. 112, 607-614.]); Ranganathan et al. (2000[Ranganathan, A., Pedireddi, V. R., Sanjayan, G. & Rao, C. N. R. (2000). J. Mol. Struct. 522, 87-94.]); Prior et al. (2013[Prior, T. J., Armstrong, J. A., Benoit, D. M. & Marshall, K. L. (2013). CrystEngComm, 15, 5838-5843.]). For cyanurate and tri­thio­cyanurate salts, see: Krepps et al. (2001[Krepps, M., Parkin, S. & Atwood, D. A. (2001). Cryst. Growth Des. 1, 291-207.]); Barszcz et al. (2006[Barszcz, B., Lapinski, A., Graja, A., Flakina, A. M., Chekhlov, A. N. & Lyubovskaya, R. N. (2006). Chem. Phys. 330, 486-494.]); Yang (2010[Yang, Y. (2010). Acta Cryst. E66, o2793.]); Nichol & Clegg (2006[Nichol, G. S. & Clegg, W. (2006). Cryst. Growth Des. 6, 451-460.]); Hou & Yang (2011[Hou, Y. & Yang, Y. (2011). Acta Cryst. E67, o44.]); El-Gamel et al. (2008[El-Gamel, N. E. A., Wagler, J. & Kroke, E. (2008). J. Mol. Struct. 888, 204-213.]). For a common hydrogen-bond motif in cyanurates and tri­thio­cyanurates, see: Falvello et al. (1997[Falvello, L. R., Pascual, I., Tomás, M. & Urriolabeitia, E. P. (1997). J. Am. Chem. Soc. 119, 11894-11902.]); Sivashankar (2000[Sivashankar, K. (2000). Proc. Indian Acad. Sci. Chem. Sci. 112, 607-614.]); Hou & Yang (2011[Hou, Y. & Yang, Y. (2011). Acta Cryst. E67, o44.]).

[Scheme 1]

Experimental

Crystal data
  • C9H14NO+·C3H2N3O3-

  • Mr = 280.29

  • Monoclinic, C 2/c

  • a = 21.0855 (3) Å

  • b = 14.0236 (2) Å

  • c = 10.0626 (1) Å

  • [beta] = 115.474 (1)°

  • V = 2686.18 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 298 K

  • 0.47 × 0.12 × 0.09 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.68, Tmax = 0.75

  • 16557 measured reflections

  • 2753 independent reflections

  • 1913 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.115

  • S = 1.02

  • 2753 reflections

  • 197 parameters

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

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3...O2i 0.921 (19) 1.841 (19) 2.7609 (17) 176.5 (16)
N5-H5...O4ii 0.879 (19) 1.97 (2) 2.8434 (17) 172.9 (17)
O1-H1...N1 0.91 (2) 1.82 (2) 2.7103 (17) 169 (2)
N2-H2A...O2iii 0.942 (19) 1.979 (19) 2.8612 (17) 155.2 (16)
N2-H2B...O1iii 0.939 (19) 2.003 (19) 2.835 (2) 146.6 (16)
Symmetry codes: (i) [-x+1, y, -z+{\script{1\over 2}}]; (ii) [-x+1, y, -z+{\script{3\over 2}}]; (iii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z].

Data collection: APEX2 (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QK2061 ).


Acknowledgements

RRM and DMM thank Dr Ruben A. Toscano for technical assistance. Support of this research by CONACyT (CB 2010-154732) and PAPIIT (IN201711-3) is acknowledged. ESJ thanks PROMEP "Apoyo a perfil deseable".

References

Barszcz, B., Lapinski, A., Graja, A., Flakina, A. M., Chekhlov, A. N. & Lyubovskaya, R. N. (2006). Chem. Phys. 330, 486-494.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
El-Gamel, N. E. A., Wagler, J. & Kroke, E. (2008). J. Mol. Struct. 888, 204-213.  [ChemPort]
Falvello, L. R., Pascual, I., Tomás, M. & Urriolabeitia, E. P. (1997). J. Am. Chem. Soc. 119, 11894-11902.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Hou, Y. & Yang, Y. (2011). Acta Cryst. E67, o44.  [CrossRef] [IUCr Journals]
Krepps, M., Parkin, S. & Atwood, D. A. (2001). Cryst. Growth Des. 1, 291-207.  [CSD] [CrossRef] [ChemPort]
Nichol, G. S. & Clegg, W. (2006). Cryst. Growth Des. 6, 451-460.  [CSD] [CrossRef] [ChemPort]
Prior, T. J., Armstrong, J. A., Benoit, D. M. & Marshall, K. L. (2013). CrystEngComm, 15, 5838-5843.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Ranganathan, A., Pedireddi, V. R., Sanjayan, G. & Rao, C. N. R. (2000). J. Mol. Struct. 522, 87-94.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sivashankar, K. (2000). Proc. Indian Acad. Sci. Chem. Sci. 112, 607-614.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yang, Y. (2010). Acta Cryst. E66, o2793.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1741-o1742   [ doi:10.1107/S1600536813029383 ]

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