[Journal logo]

Volume 69 
Part 6 
Pages o968-o969  
June 2013  

Received 7 May 2013
Accepted 20 May 2013
Online 25 May 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.003 Å
R = 0.062
wR = 0.157
Data-to-parameter ratio = 19.2
Details
Open access

6-(4-Methylphenyl)-1,3,5-triazine-2,4-diamine-benzoic acid (1/1)

aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Chemistry, Government Arts College (Autonomous), Thanthonimalai, Karur 639 005, Tamil Nadu, India
Correspondence e-mail: arazaki@usm.my

The benzoic acid molecule of the title adduct, C10H11N5·C7H6O2, is approximately planar, with a dihedral angle of 7.2 (3)° between the carboxylic acid group and the benzene ring. In the triazine molecule, the plane of the triazine ring makes a dihedral angle of 28.85 (9)° with that of the adjacent benzene ring. In the crystal, the two components are linked by N-H...O and O-H...N hydrogen bonds with an R22(8) motif, thus generating a 1 + 1 unit of triazine and benzoic acid molecules. The acid-base units are further connected by N-H...N hydrogen bonds with R22(8) motifs, forming a supramolecular ribbon along [101]. The crystal structure also features weak [pi]-[pi] [centroid-centroid distances = 3.7638 (12) and 3.6008 (12) Å] and C-H...[pi] interactions.

Related literature

For the biological activity of triazine derivatives, see: Bork et al. (2003[Bork, J. T., Lee, J. W., Khersonsky, S. M., Moon, H. S. & Chang, Y. T. (2003). Org. Lett. 5, 117-120.]). For related structures, see: Thanigaimani et al. (2007[Thanigaimani, K., Muthiah, P. T. & Lynch, D. E. (2007). Acta Cryst. E63, o4450-o4451.], 2012a[Thanigaimani, K., Razak, I. A., Arshad, S., Jagatheesan, R. & Santhanaraj, K. J. (2012a). Acta Cryst. E68, o2910.],b[Thanigaimani, K., Razak, I. A., Arshad, S., Jagatheesan, R. & Santhanaraj, K. J. (2012b). Acta Cryst. E68, o2938-o2939.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). 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.]). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C10H11N5·C7H6O2

  • Mr = 323.36

  • Triclinic, [P \overline 1]

  • a = 7.4324 (5) Å

  • b = 10.9717 (3) Å

  • c = 11.2267 (3) Å

  • [alpha] = 117.202 (1)°

  • [beta] = 101.645 (2)°

  • [gamma] = 94.032 (2)°

  • V = 783.47 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.53 × 0.43 × 0.21 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.952, Tmax = 0.980

  • 16402 measured reflections

  • 4578 independent reflections

  • 3744 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.157

  • S = 1.11

  • 4578 reflections

  • 238 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2-C7 ring.

D-H...A D-H H...A D...A D-H...A
N4-H1N4...N2i 0.839 (19) 2.19 (2) 3.021 (2) 172 (2)
N4-H2N4...O2ii 0.86 (3) 2.11 (3) 2.965 (3) 172 (3)
N5-H1N5...N3iii 0.85 (3) 2.14 (3) 2.984 (3) 169 (3)
O1-H1O1...N1iv 0.83 (3) 1.80 (3) 2.613 (2) 167 (3)
C1-H1B...Cg2v 0.98 2.75 3.661 (2) 156
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z+1; (iii) -x+2, -y+1, -z+2; (iv) x, y-1, z-1; (v) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: IS5271 ).


Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant (No. 304/PFIZIK/6312078) to conduct this work. KT thanks The Academy of Sciences for the Developing World and USM for a TWAS-USM fellowship.

References

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bork, J. T., Lee, J. W., Khersonsky, S. M., Moon, H. S. & Chang, Y. T. (2003). Org. Lett. 5, 117-120.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
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]
Thanigaimani, K., Muthiah, P. T. & Lynch, D. E. (2007). Acta Cryst. E63, o4450-o4451.  [CSD] [CrossRef] [ChemPort] [details]
Thanigaimani, K., Razak, I. A., Arshad, S., Jagatheesan, R. & Santhanaraj, K. J. (2012a). Acta Cryst. E68, o2910.  [CSD] [CrossRef] [details]
Thanigaimani, K., Razak, I. A., Arshad, S., Jagatheesan, R. & Santhanaraj, K. J. (2012b). Acta Cryst. E68, o2938-o2939.  [CSD] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o968-o969   [ doi:10.1107/S1600536813013883 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.