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Volume 66 
Part 8 
Page o1900  
August 2010  

Received 21 June 2010
Accepted 24 June 2010
Online 3 July 2010

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.060
wR = 0.176
Data-to-parameter ratio = 15.0
Details
Open access

N-(4-Methylphenyl)-6-(pyrazol-1-yl)pyridazin-3-amine

Abdul Qayyum Ather,a M. Nawaz Tahir,b* Misbahul Ain Khan,c Muhammad Makshoof Athard and Eliana Aparecida Silicz Buenoe

aDepartment of Chemistry, Islamia University, Bahawalpur, Pakistan, Applied Chemistry Research Center, PCSIR Laboratories Complex, Lahore 54600, Pakistan,bDepartment of Physics, University of Sargodha, Sargodha, Pakistan,cDepartment of Chemistry, Islamia University, Bahawalpur, Pakistan,dInstitute of Chemistry, University of the Punjab, Lahore, Pakistan, and eInstituto de Quimica, Universidade Estadual de Londrina, Londrina, Pr., Brazil
Correspondence e-mail: dmntahir_uos@yahoo.com

In the title compound, C14H13N5, the pyrazole ring is disordered over two orientations in a 0.571 (10):0.429 (10) ratio and the dihedral angle between the pyridazine ring and the benzene ring is 28.07 (10)°. In the crystal, pairs of N-H...N and C-H...N hydrogen bonds link the molecules into dimers, with the aid of a crystallographic twofold axis. The packing is consolidated by further C-H...N bonds and weak C-H...[pi] interactions.

Related literature

For related structures, see: Ather et al. (2009[Ather, A. Q., Tahir, M. N., Khan, M. A. & Athar, M. M. (2009). Acta Cryst. E65, o1628.], 2010a[Ather, A. Q., Sahin, O., Khan, I. U., Khan, M. A. & Büyükgüngör, O. (2010a). Acta Cryst. E66, o1295.],b[Ather, A. Q., Tahir, M. N., Khan, M. A. & Athar, M. M. (2010b). Acta Cryst. E66, o1327.],c[Ather, A. Q., Tahir, M. N., Khan, M. A., Athar, M. M. & Bueno, E. A. S. (2010c). Acta Cryst. E66, o2016.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C14H13N5

  • Mr = 251.29

  • Monoclinic, C 2/c

  • a = 31.8677 (17) Å

  • b = 7.9408 (5) Å

  • c = 10.8446 (7) Å

  • [beta] = 109.715 (3)°

  • V = 2583.4 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.32 × 0.18 × 0.16 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.982, Tmax = 0.988

  • 9293 measured reflections

  • 2336 independent reflections

  • 1384 reflections with I > 2[sigma](I)

  • Rint = 0.059
Refinement

  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.176

  • S = 1.03

  • 2336 reflections

  • 156 parameters

  • 11 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N4/N5B/C12B-C14B ring.
D-H...A D-H H...A D...A D-H...A
N1-H1...N2i 0.86 2.12 2.982 (3) 178
C6-H6...N3i 0.93 2.62 3.498 (4) 157
C14B-H14B...N5Bii 0.93 2.47 3.357 (11) 160
C5-H5...Cg1iii 0.93 2.99 3.527 (5) 118
Symmetry codes: (i) [-x, y, -z+{\script{3\over 2}}]; (ii) [x, -y+1, z+{\script{1\over 2}}]; (iii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5514 ).

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Bana International, Karachi, Pakistan.

References

Ather, A. Q., Sahin, O., Khan, I. U., Khan, M. A. & Büyükgüngör, O. (2010a). Acta Cryst. E66, o1295.  [CrossRef] [details]
Ather, A. Q., Tahir, M. N., Khan, M. A. & Athar, M. M. (2009). Acta Cryst. E65, o1628.  [CSD] [CrossRef] [details]
Ather, A. Q., Tahir, M. N., Khan, M. A. & Athar, M. M. (2010b). Acta Cryst. E66, o1327.  [CrossRef] [details]
Ather, A. Q., Tahir, M. N., Khan, M. A., Athar, M. M. & Bueno, E. A. S. (2010c). Acta Cryst. E66, o2016.  [CrossRef] [details]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2010). E66, o1900  [ doi:10.1107/S1600536810024700 ]

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