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Volume 69 
Part 6 
Page o970  
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) = 0.006 Å
R = 0.055
wR = 0.135
Data-to-parameter ratio = 7.9
Details
Open access

6-(4-Methylphenyl)-1,3,5-triazine-2,4-diamine-4-methylbenzoic 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 4-methylbenzoic acid molecule of the title adduct, C10H11N5·C8H8O2, is approximately planar with a dihedral angle of 6.3 (2)° between the carboxylic acid group and the benzene ring. In the triazine molecule, the plane of the triazine ring makes a dihedral angle of 29.2 (2)° with that of the adjacent benzene ring. In the crystal, the acid and base molecules are linked via N-H...O and O-H...N hydrogen bonds with an R22(8) motif, and the acid-base pairs are further connected via N-H...N hydrogen bonds with R22(8) motifs, forming a supramolecular ribbon along [101]. Between the tapes, a weak C-H...[pi] interaction is observed.

Related literature

The background to this study has been described in the preceding paper, see: Thanigaimani et al. (2013[Thanigaimani, K., Khalib, N. C., Razak, I. A., Lavanya, P. & Balasubramani, K. (2013). Acta Cryst. E69, o968-o969.]). 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·C8H8O2

  • Mr = 337.38

  • Monoclinic, C c

  • a = 11.1271 (3) Å

  • b = 20.9492 (6) Å

  • c = 7.4189 (2) Å

  • [beta] = 101.321 (2)°

  • V = 1695.73 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.40 × 0.40 × 0.20 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 = 0.965, Tmax = 0.982

  • 8715 measured reflections

  • 1932 independent reflections

  • 1811 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.135

  • S = 1.19

  • 1932 reflections

  • 244 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4-C9 ring.

D-H...A D-H H...A D...A D-H...A
O2-H1O2...N2 0.77 (6) 1.92 (6) 2.682 (4) 171 (6)
N4-H1N4...O1 0.97 (6) 1.98 (6) 2.936 (5) 169 (6)
N4-H2N4...N3i 0.84 (4) 2.26 (4) 3.099 (5) 172 (4)
N5-H1N5...N1ii 0.90 (6) 2.11 (6) 3.003 (5) 173 (5)
C10-H10C...Cg2iii 0.98 2.83 3.723 (6) 152
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+1, z-{\script{1\over 2}}].

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: IS5272 ).


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]
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., Khalib, N. C., Razak, I. A., Lavanya, P. & Balasubramani, K. (2013). Acta Cryst. E69, o968-o969.  [CrossRef] [details]


Acta Cryst (2013). E69, o970  [ doi:10.1107/S1600536813013895 ]

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