3-Chloro-6-[2-(cyclo­pentyl­idene)hydrazin-1-yl]pyridazine

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

doi:10.1107/S1600536811011342

. 2011 Mar 31;67(Pt 4):o1020. doi: 10.1107/S1600536811011342

3-Chloro-6-[2-(cyclopentylidene)hydrazin-1-yl]pyridazine

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

PMCID: PMC3099815 PMID: 21754036

Abstract

The asymmetric unit of the title compound, C₉H₁₁ClN₄, contains two virtually planar molecules that differ in conformation about the bond connecting the hydrazine and pyridazine units. The 3-chloro-6-hydrazinylpyridazine and cyclopentane groups are oriented at dihedral angles of 4.5 (3) and 8.8 (4)° in the two molecules. In the crystal, the molecules form a one dimensional polymeric structure extending along the a axis via N—H⋯N hydrogen bonds. The crystal stucired was an inversion twin [ratio of the twin domains = 0.73 (9):0.27 (9)].

Related literature

For related structures, see: Ather et al. (2010a ▶,b ▶,c ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₉H₁₁ClN₄
M _r = 210.67
Orthorhombic,
a = 10.180 (5) Å
b = 9.870 (5) Å
c = 20.049 (3) Å
V = 2014.5 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 296 K
0.30 × 0.15 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.942, T _max = 0.950
7740 measured reflections
3355 independent reflections
2130 reflections with I > 2σ(I)
R _int = 0.044

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.120
S = 1.00
3355 reflections
254 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ▶), 1307 Friedel pairs
Flack parameter: 0.73 (9)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536811011342/gk2360sup1.cif

e-67-o1020-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011342/gk2360Isup2.hkl

e-67-o1020-Isup2.hkl^{(161.2KB, 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
N3—H3A⋯N5ⁱ	0.86	2.52	3.295 (5)	150
N3—H3A⋯N6ⁱ	0.86	2.27	3.088 (5)	159
N7—H7⋯N1ⁱⁱ	0.86	2.19	3.041 (5)	170

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

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the 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.

supplementary crystallographic information

Comment

In continuation to on our studies on 3-chloro-6-hydrazinylpyridazine derivatives (Ather et al., 2010a,b,c), the title compound (Fig. 1) is being reported here.

There are two symmetry independent molecule in the asymmetric unit of title compound that differ in conformation. In one molecule 3-chloro-6-hydrazinylpyridazine moiety A (C1—C4/N1—N4/CL1) and cyclopentane group B (C5–C9) are planar with r. m. s. deviations of 0.0104 and 0.0354 Å. The dihedral angle between A/B is 8.5 (4)°. In the second symmetry independent molecule 3-chloro-6-hydrazinylpyridazine moiety C (C10—C13/N5—N8/CL2) and cyclopentane gruop D (C14–C18) are also planar with r. m. s. deviations of 0.0068 and 0.0046 Å. The dihedral angle between C/D is 4.5 (3)°. The title compound consists of one dimensional polymeric chains via N–H···N hydrogen bonds extending along the crystallographic a-axis (Table 1, Fig. 2).

Experimental

3-Chloro-6-hydrazinylpyridazine (0.5 g, 3.46 mmol), dissolved in ethanol (10 ml) and refluxed for 15 min. Cyclopentanone (0.291 g, 3.459 mmol) was added to the formar solution and refluxed about 3 h, till the completion of reaction monitored through TLC. On completion of the reaction mixture was concenterated under vacuum. The crude product was recrystallized in ethanol which yielded the light yellow needles of the title compound.