N-Phenyl-6-(1H-pyrazol-1-yl)pyridazin-3-amine

Abdul Qayyum Ather; M Nawaz Tahir; Misbahul Ain Khan; Muhammad Makshoof Athar

doi:10.1107/S1600536810016697

. 2010 May 12;66(Pt 6):o1327. doi: 10.1107/S1600536810016697

N-Phenyl-6-(1H-pyrazol-1-yl)pyridazin-3-amine

Abdul Qayyum Ather ^a,^b, M Nawaz Tahir ^c,^*, Misbahul Ain Khan ^a, Muhammad Makshoof Athar ^d

PMCID: PMC2979482 PMID: 21579418

Abstract

The molecule of title compound, C₁₃H₁₁N₅, is essentially planar (r.m.s. deviation = 0.0440 Å) and an intramolecular C—H⋯N hydrogen bond generates an S(6) motif. In the crystal, molecules are connected into chains by intermolecular N—H⋯N and C—H⋯N hydrogen bonds. In addition, π–π stacking interactions are observed between the pyrazole and pyridazine rings [interplanar distance = 3.6859 (10) Å].

Related literature

For a related structure, see: Ather et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₃H₁₁N₅
M _r = 237.27
Orthorhombic,
a = 11.3533 (7) Å
b = 9.4214 (5) Å
c = 21.6603 (14) Å
V = 2316.9 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.982, T _max = 0.988
10085 measured reflections
2754 independent reflections
1571 reflections with I > 2σ(I)
R _int = 0.045

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.119
S = 0.99
2754 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016697/gk2271sup1.cif

e-66-o1327-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016697/gk2271Isup2.hkl

e-66-o1327-Isup2.hkl^{(132.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N5ⁱ	0.86	2.22	3.071 (2)	173
C6—H6⋯N2	0.93	2.37	2.966 (3)	122
C8—H8⋯N3ⁱⁱ	0.93	2.60	3.265 (2)	129

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

In continuation of our studies on pyrazolylpyridazine derivatives (Ather et al., 2009), the structure of title compound ( Fig. 1) is reported here.

The title compound contains pyrazole, pyridazine and benzene rings. The r. m. s. deviation of 0.044 Å shows that the molecule of title compound is essentially planar. There exist S(6) ring motif (Bernstein et al., 1995) due to C–H···N intramolecular H-bonding (Fig. 1). The molecules are stabilized in the form of infinite polymeric chains due to intermolecular H-bondings (Table 1) extending along the crystallographic b-axis (Fig. 2). The π–π interactions between the pyrazol and pyridazine ring are present at a distance of 3.6859 (10) Å.

Experimental

3-Chloro-6-(1H-pyrazole-1-yl)pyridazine (1 g, 5.5 mmol) was dissolved in xylene (15 ml). Aniline (0.516 g, 5.5 mmol) was added to the solution and refluxed for 12 h. The reaction was monitored by TLC. After the completion, the reaction mixture was concentrated under vacuum. Distilled water (50 ml) was added to the resulting concentrated mixture, which give rise to precipitate. The filtered precipitate was dried and recrystallized from chloroform to obtain the title compound (I).