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Volume 69 
Part 11 
Pages o1717-o1718  
November 2013  

Received 17 October 2013
Accepted 22 October 2013
Online 31 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.048
wR = 0.135
Data-to-parameter ratio = 56.4
Details
Open access

4-Meth­oxy-N-(pyridin-4-ylmeth­yl)-3-(tri­fluoro­meth­yl)benzamide monohydrate

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, India,cDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and dDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
Correspondence e-mail: pasuchetan@yahoo.co.in

In the title compound, C15H13F3N2O2·H2O, the dihedral angle between the benzene and pyridine rings is 74.97 (1)°. The -CF3 group attached to the benzene ring is syn to the C=O bond in the adjacent side chain. In the crystal, mol­ecules are linked to one another through the water mol­ecules by strong N-H...O, O-H...O and O-H...N hydrogen bonds, forming a ladder-type network. The benzamide mol­ecules are also linked to one another through C-H...F inter­actions, forming C(6) chains parallel to the b-axis direction. Aromatic [pi]-[pi] stacking inter­actions [centroid-centroid separations = 3.7150 (1) and 3.7857 (1) Å] between adjacent pairs of pyridine and benzene rings are also observed, resulting in a three-dimensional architecture are also observed.

Related literature

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 the biological activity of amides, see: Manojkumar et al. (2013a[Manojkumar, K. E., Sreenivasa, S., Mohan, N. R., Madhuchakrapani Rao, T. & Harikrishna, T. (2013a). J. Appl. Chem. 2, 730-737.],b[Manojkumar, K. E., Sreenivasa, S., Shivaraja, G. & Madhuchakrapani Rao, T. (2013b). Molbank. M803; doi:10.3390/M803.]); Sreenivasa et al. (2013c[Sreenivasa, S., Palakshamurthy, B. S., Lohith, T. N., Mohan, N. R., Kumar, V. & Suchetan, P. A. (2013c). Acta Cryst. E69, o1263.]). For the importance of amides containing tri­fluoro­methyl substituents as pharmacophores, see: Sreenivasa et al. (2013a[Sreenivasa, S., ManojKumar, K. E., Kempaiah, A., Suchetan, P. A. & Palakshamurthy, B. S. (2013a). Acta Cryst. E69, o761.]) and for amides providing structural rigidity to the mol­ecules, see: Sreenivasa et al. (2013b[Sreenivasa, S., ManojKumar, K. E., Suchetan, P. A., Tonannavar, J., Chavan, Y. & Palakshamurthy, B. S. (2013b). Acta Cryst. E69, o185.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13F3N2O2·H2O

  • Mr = 328.29

  • Triclinic, [P \overline 1]

  • a = 7.2687 (13) Å

  • b = 7.8758 (14) Å

  • c = 14.177 (3) Å

  • [alpha] = 104.071 (10)°

  • [beta] = 99.672 (10)°

  • [gamma] = 97.21 (1)°

  • V = 764.2 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 296 K

  • 0.34 × 0.28 × 0.22 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: [psi] scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.959, Tmax = 0.973

  • 11967 measured reflections

  • 11967 independent reflections

  • 9619 reflections with I > 2[sigma](I)

Refinement
  • R[F2 > 2[sigma](F2)] = 0.048

  • wR(F2) = 0.135

  • S = 1.06

  • 11967 reflections

  • 212 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-HN1...O3i 0.86 2.12 2.9119 (14) 152
O3-H1O...N2 0.85 2.01 2.8402 (15) 166
O3-H2O...O2ii 0.85 2.20 2.9646 (13) 149
C6-H6...F3iii 0.93 2.46 3.3963 (15) 173
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y-1, -z; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5360 ).


Acknowledgements

The authors thank Professor T. N. Guru Row, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for his help and valuable suggestions.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
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.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Manojkumar, K. E., Sreenivasa, S., Mohan, N. R., Madhuchakrapani Rao, T. & Harikrishna, T. (2013a). J. Appl. Chem. 2, 730-737.  [ChemPort]
Manojkumar, K. E., Sreenivasa, S., Shivaraja, G. & Madhuchakrapani Rao, T. (2013b). Molbank. M803; doi:10.3390/M803.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sreenivasa, S., ManojKumar, K. E., Kempaiah, A., Suchetan, P. A. & Palakshamurthy, B. S. (2013a). Acta Cryst. E69, o761.  [CrossRef] [IUCr Journals]
Sreenivasa, S., ManojKumar, K. E., Suchetan, P. A., Tonannavar, J., Chavan, Y. & Palakshamurthy, B. S. (2013b). Acta Cryst. E69, o185.  [CSD] [CrossRef] [IUCr Journals]
Sreenivasa, S., Palakshamurthy, B. S., Lohith, T. N., Mohan, N. R., Kumar, V. & Suchetan, P. A. (2013c). Acta Cryst. E69, o1263.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1717-o1718   [ doi:10.1107/S1600536813029103 ]

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