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Volume 68 
Part 11 
Page o3193  
November 2012  

Received 22 August 2012
Accepted 15 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.095
Data-to-parameter ratio = 11.4
Details
Open access

1,5-Dimethyl-2-phenyl-4-[phenyl(pyridin-2-ylamino)methyl]-1H-pyrazol-3(2H)-one

aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, Tamilnadu, India,bDepartment of Physics, Bishop Heber College (Autonomous), Tiruchirappalli 620 017, Tamilnadu, India, and cDepartment of Physics, National Institute of Technology, Tiruchirappalli 620 015, Tamilnadu, India
Correspondence e-mail: xrdfrank@yahoo.co.in

In the title compound, C23H22N4O, the pyrazole ring makes dihedral angles of 45.57 (11)° with the attached phenyl ring, and 83.98 (10) and 67.85 (10) °, respectively, with the other phenyl ring and the pyridyl ring. The pyridyl ring makes a dihedral angle of 80.15 (10)° with the adjacent phenyl ring. In the crystal, N-H...O hydrogen bonds supplemented by weak C-H...O hydrogen bonds link the molecules into chains which run parallel to the a-axis direction.

Related literature

For the origin of the material studied, see: Vijayan (1971[Vijayan, M. (1971). Curr. Sci. 40, 262-264.]); Singh & Vijayan (1973[Singh, T. P. & Vijayan, M. (1973). Acta Cryst. B29, 714-720.]). For related structures, see: Singh & Vijayan (1974[Singh, T. P. & Vijayan, M. (1974). Acta Cryst. B30, 557-562.], 1976[Singh, T. P. & Vijayan, M. (1976). Acta Cryst. B32, 2432-2437.]); Tordjman et al. (1991[Tordjman, I., Durif, A. & Masse, R. (1991). Acta Cryst. C47, 351-353.]); Yadav et al. (2003[Yadav, P. N., Demertzis, M. A., Kovala-Demertzi, D., Skoulika, S. & West, D. X. (2003). Inorg. Chim. Acta, 349, 30-36.]); Li & Zhang (2004[Li, Z.-X. & Zhang, X.-L. (2004). Acta Cryst. E60, o2199-o2200.]); Wen (2005[Wen, P. (2005). Acta Cryst. E61, o2918-o2920.]); Sun et al. (2007[Sun, Y.-F., Li, J.-K., Zheng, Z.-B. & Wu, R.-T. (2007). Acta Cryst. E63, o2522-o2523.]).

[Scheme 1]

Experimental

Crystal data
  • C23H22N4O

  • Mr = 370.45

  • Orthorhombic, P 21 21 21

  • a = 5.701 (5) Å

  • b = 12.485 (5) Å

  • c = 26.736 (5) Å

  • V = 1903.0 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 273 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.976, Tmax = 0.984

  • 14432 measured reflections

  • 2959 independent reflections

  • 2337 reflections with I > 2[sigma](I)

  • Rint = 0.036

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

  • wR(F2) = 0.095

  • S = 1.01

  • 2959 reflections

  • 259 parameters

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

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O1i 0.85 (3) 2.16 (3) 2.982 (3) 161 (2)
C18-H18...O1i 0.93 2.58 3.335 (3) 138
C23-H23C...O1ii 0.96 2.59 3.512 (3) 162
Symmetry codes: (i) x-1, y, z; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2004[Bruker (2004). APEX2, 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: 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: GO2065 ).


Acknowledgements

The authors thank the SAIF at IITM Chennai, sponsored by DST India, for providing analytical facilities.

References

Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Li, Z.-X. & Zhang, X.-L. (2004). Acta Cryst. E60, o2199-o2200.  [CSD] [CrossRef] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Singh, T. P. & Vijayan, M. (1973). Acta Cryst. B29, 714-720.  [CrossRef] [ChemPort] [details] [ISI]
Singh, T. P. & Vijayan, M. (1974). Acta Cryst. B30, 557-562.  [CrossRef] [ChemPort] [details] [ISI]
Singh, T. P. & Vijayan, M. (1976). Acta Cryst. B32, 2432-2437.  [CrossRef] [details] [ISI]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sun, Y.-F., Li, J.-K., Zheng, Z.-B. & Wu, R.-T. (2007). Acta Cryst. E63, o2522-o2523.  [CSD] [CrossRef] [details]
Tordjman, I., Durif, A. & Masse, R. (1991). Acta Cryst. C47, 351-353.  [CrossRef] [details]
Vijayan, M. (1971). Curr. Sci. 40, 262-264.  [ChemPort]
Wen, P. (2005). Acta Cryst. E61, o2918-o2920.  [CSD] [CrossRef] [details]
Yadav, P. N., Demertzis, M. A., Kovala-Demertzi, D., Skoulika, S. & West, D. X. (2003). Inorg. Chim. Acta, 349, 30-36.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3193  [ doi:10.1107/S1600536812042936 ]

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