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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1327.
Published online 2010 May 12. doi:  10.1107/S1600536810016697
PMCID: PMC2979482

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

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 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

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Object name is e-66-o1327-scheme1.jpg

Experimental

Crystal data

  • C13H11N5
  • M r = 237.27
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1327-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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).

Figures

Fig. 1.
View of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radii. The dotted line indicates the intramolecular hydrogen bond.
Fig. 2.
Packing diagram of the title compound (PLATON: Spek, 2009) showing that infinite polymeric chains extend along the b-axis.

Crystal data

C13H11N5F(000) = 992
Mr = 237.27Dx = 1.360 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2920 reflections
a = 11.3533 (7) Åθ = 2.6–27.9°
b = 9.4214 (5) ŵ = 0.09 mm1
c = 21.6603 (14) ÅT = 296 K
V = 2316.9 (2) Å3Prismatic, pale brown
Z = 80.30 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer2754 independent reflections
Radiation source: fine-focus sealed tube1571 reflections with I > 2σ(I)
graphiteRint = 0.045
Detector resolution: 7.50 pixels mm-1θmax = 27.9°, θmin = 2.6°
ω scanh = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −12→8
Tmin = 0.982, Tmax = 0.988l = −17→28
10085 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0546P)2 + 0.0495P] where P = (Fo2 + 2Fc2)/3
2754 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = −0.15 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
C10.22072 (14)−0.09114 (16)0.11333 (7)0.0450 (4)
C20.17051 (16)−0.18861 (17)0.07303 (8)0.0588 (5)
H20.0892−0.20080.07290.071*
C30.23913 (19)−0.2677 (2)0.03321 (9)0.0685 (5)
H30.2040−0.33270.00660.082*
C40.35859 (18)−0.2505 (2)0.03286 (9)0.0676 (5)
H40.4052−0.30270.00590.081*
C50.40882 (17)−0.1552 (2)0.07273 (9)0.0694 (5)
H50.4902−0.14400.07270.083*
C60.34133 (15)−0.07516 (18)0.11315 (9)0.0579 (5)
H60.3772−0.01120.13990.069*
C70.15904 (13)0.08370 (16)0.19601 (7)0.0432 (4)
C80.05780 (14)0.14252 (16)0.22366 (8)0.0499 (4)
H8−0.01690.11390.21130.060*
C90.07086 (14)0.24049 (17)0.26820 (8)0.0499 (4)
H90.00660.28240.28760.060*
C100.18694 (13)0.27585 (16)0.28379 (7)0.0422 (4)
C110.31668 (15)0.42876 (18)0.34775 (9)0.0561 (5)
H110.38920.40550.33050.067*
C120.29780 (17)0.52176 (19)0.39459 (9)0.0608 (5)
H120.35370.57480.41590.073*
C130.17754 (17)0.52036 (18)0.40374 (8)0.0596 (5)
H130.13920.57500.43330.072*
N10.14245 (11)−0.01684 (14)0.15110 (6)0.0493 (4)
H10.0698−0.03830.14500.059*
N20.26728 (11)0.12101 (13)0.21296 (6)0.0473 (4)
N30.27965 (11)0.22007 (14)0.25801 (6)0.0468 (3)
N40.21109 (11)0.37648 (13)0.33089 (6)0.0452 (3)
N50.12287 (12)0.43206 (15)0.36555 (7)0.0558 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0436 (9)0.0463 (9)0.0452 (9)0.0013 (7)−0.0012 (8)0.0076 (8)
C20.0529 (10)0.0656 (11)0.0579 (11)−0.0040 (9)−0.0040 (9)−0.0029 (10)
C30.0790 (14)0.0682 (12)0.0583 (12)−0.0014 (11)−0.0065 (11)−0.0114 (10)
C40.0691 (14)0.0739 (13)0.0599 (12)0.0118 (11)0.0068 (10)−0.0065 (10)
C50.0490 (11)0.0843 (13)0.0748 (13)0.0052 (10)0.0041 (10)−0.0132 (12)
C60.0465 (10)0.0645 (11)0.0627 (12)−0.0005 (9)0.0009 (9)−0.0095 (9)
C70.0336 (8)0.0461 (9)0.0499 (9)−0.0005 (7)−0.0016 (7)0.0067 (8)
C80.0290 (8)0.0585 (10)0.0621 (11)−0.0005 (7)−0.0047 (8)−0.0022 (9)
C90.0313 (8)0.0592 (10)0.0593 (11)0.0049 (7)0.0002 (8)−0.0038 (9)
C100.0340 (8)0.0457 (9)0.0468 (9)0.0011 (7)−0.0031 (7)0.0051 (8)
C110.0400 (9)0.0635 (11)0.0648 (12)−0.0036 (8)−0.0072 (8)−0.0002 (10)
C120.0606 (12)0.0602 (11)0.0617 (12)−0.0044 (9)−0.0155 (10)−0.0052 (10)
C130.0632 (12)0.0617 (11)0.0540 (11)0.0092 (9)−0.0080 (10)−0.0076 (9)
N10.0329 (7)0.0563 (8)0.0585 (9)−0.0031 (6)−0.0016 (6)−0.0046 (7)
N20.0337 (7)0.0552 (8)0.0531 (8)−0.0003 (6)−0.0012 (6)−0.0023 (7)
N30.0308 (7)0.0557 (8)0.0539 (8)0.0006 (6)−0.0015 (6)−0.0007 (7)
N40.0347 (7)0.0517 (8)0.0491 (8)0.0031 (6)−0.0038 (6)0.0038 (7)
N50.0435 (8)0.0649 (9)0.0589 (10)0.0100 (7)0.0008 (7)−0.0042 (8)

Geometric parameters (Å, °)

C1—C61.378 (2)C8—H80.9300
C1—C21.389 (2)C9—C101.401 (2)
C1—N11.3961 (19)C9—H90.9300
C2—C31.381 (2)C10—N31.3022 (19)
C2—H20.9300C10—N41.4194 (19)
C3—C41.366 (3)C11—N41.3465 (19)
C3—H30.9300C11—C121.358 (2)
C4—C51.370 (2)C11—H110.9300
C4—H40.9300C12—C131.380 (3)
C5—C61.387 (2)C12—H120.9300
C5—H50.9300C13—N51.327 (2)
C6—H60.9300C13—H130.9300
C7—N21.3300 (18)N1—H10.8600
C7—N11.371 (2)N2—N31.3574 (17)
C7—C81.410 (2)N4—N51.3570 (17)
C8—C91.343 (2)
C6—C1—C2118.58 (16)C8—C9—C10116.13 (15)
C6—C1—N1125.41 (15)C8—C9—H9121.9
C2—C1—N1116.01 (15)C10—C9—H9121.9
C3—C2—C1121.18 (18)N3—C10—C9124.14 (15)
C3—C2—H2119.4N3—C10—N4114.93 (13)
C1—C2—H2119.4C9—C10—N4120.92 (14)
C4—C3—C2119.97 (18)N4—C11—C12107.35 (16)
C4—C3—H3120.0N4—C11—H11126.3
C2—C3—H3120.0C12—C11—H11126.3
C3—C4—C5119.20 (18)C11—C12—C13104.92 (16)
C3—C4—H4120.4C11—C12—H12127.5
C5—C4—H4120.4C13—C12—H12127.5
C4—C5—C6121.63 (18)N5—C13—C12112.29 (16)
C4—C5—H5119.2N5—C13—H13123.9
C6—C5—H5119.2C12—C13—H13123.9
C1—C6—C5119.44 (17)C7—N1—C1132.45 (13)
C1—C6—H6120.3C7—N1—H1113.8
C5—C6—H6120.3C1—N1—H1113.8
N2—C7—N1120.37 (14)C7—N2—N3118.41 (13)
N2—C7—C8122.16 (15)C10—N3—N2120.13 (13)
N1—C7—C8117.46 (14)C11—N4—N5111.46 (14)
C9—C8—C7119.03 (15)C11—N4—C10127.68 (14)
C9—C8—H8120.5N5—N4—C10120.86 (13)
C7—C8—H8120.5C13—N5—N4103.98 (14)
C6—C1—C2—C3−0.4 (2)C6—C1—N1—C7−1.0 (3)
N1—C1—C2—C3179.63 (15)C2—C1—N1—C7178.96 (16)
C1—C2—C3—C4−0.2 (3)N1—C7—N2—N3−179.41 (13)
C2—C3—C4—C50.6 (3)C8—C7—N2—N3−0.6 (2)
C3—C4—C5—C6−0.5 (3)C9—C10—N3—N20.0 (2)
C2—C1—C6—C50.5 (3)N4—C10—N3—N2179.08 (12)
N1—C1—C6—C5−179.48 (15)C7—N2—N3—C100.3 (2)
C4—C5—C6—C1−0.1 (3)C12—C11—N4—N5−0.26 (19)
N2—C7—C8—C90.6 (2)C12—C11—N4—C10179.96 (14)
N1—C7—C8—C9179.46 (14)N3—C10—N4—C116.3 (2)
C7—C8—C9—C10−0.3 (2)C9—C10—N4—C11−174.63 (16)
C8—C9—C10—N30.0 (2)N3—C10—N4—N5−173.47 (13)
C8—C9—C10—N4−179.01 (13)C9—C10—N4—N55.6 (2)
N4—C11—C12—C130.03 (19)C12—C13—N5—N4−0.37 (19)
C11—C12—C13—N50.2 (2)C11—N4—N5—C130.39 (18)
N2—C7—N1—C1−4.1 (3)C10—N4—N5—C13−179.82 (14)
C8—C7—N1—C1177.09 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···N5i0.862.223.071 (2)173
C6—H6···N20.932.372.966 (3)122
C8—H8···N3ii0.932.603.265 (2)129

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x−1/2, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2271).

References

  • Ather, A. Q., Tahir, M. N., Khan, M. A. & Athar, M. M. (2009). Acta Cryst. E65, o1628. [PMC free article] [PubMed]
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed.34, 1555–1573.
  • 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.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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