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

Krishnakumar, K.; Franklin, S.; Prabhu, G.V.; Balasubramanian, T.

doi:10.1107/S1600536812042936

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 (C-C) = 0.003 Å
R = 0.040
wR = 0.095
Data-to-parameter ratio = 11.4
Details

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

K. Krishnakumar,^a S. Franklin,^b ^* G. Venkatesa Prabhu ^a and T. Balasubramanian ^c

^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-HO hydrogen bonds supplemented by weak C-HO 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); Singh & Vijayan (1973). For related structures, see: Singh & Vijayan (1974, 1976); Tordjman et al. (1991); Yadav et al. (2003); Li & Zhang (2004); Wen (2005); Sun et al. (2007).

Experimental

Crystal data

C₂₃H₂₂N₄O
M_r = 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 radiation
= 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) T_min = 0.976, T_max = 0.984
14432 measured reflections
2959 independent reflections
2337 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(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
_max = 0.18 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO1ⁱ	0.85 (3)	2.16 (3)	2.982 (3)	161 (2)
C18-H18O1ⁱ	0.93	2.58	3.335 (3)	138
C23-H23CO1ⁱⁱ	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); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2009).

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.
Li, Z.-X. & Zhang, X.-L. (2004). Acta Cryst. E60, o2199-o2200.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, T. P. & Vijayan, M. (1973). Acta Cryst. B29, 714-720.
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Singh, T. P. & Vijayan, M. (1976). Acta Cryst. B32, 2432-2437.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sun, Y.-F., Li, J.-K., Zheng, Z.-B. & Wu, R.-T. (2007). Acta Cryst. E63, o2522-o2523.
Tordjman, I., Durif, A. & Masse, R. (1991). Acta Cryst. C47, 351-353.
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Wen, P. (2005). Acta Cryst. E61, o2918-o2920.
Yadav, P. N., Demertzis, M. A., Kovala-Demertzi, D., Skoulika, S. & West, D. X. (2003). Inorg. Chim. Acta, 349, 30-36.

organic compounds