3-(1,3-Dioxolan-2-yl)-2-hydrazino-7-methyl­quinoline

R Subashini; Venkatesha R Hathwar; P Nithya; K Prabakaran; F Nawaz Khan

doi:10.1107/S1600536809003031

. 2009 Jan 28;65(Pt 2):o407–o408. doi: 10.1107/S1600536809003031

3-(1,3-Dioxolan-2-yl)-2-hydrazino-7-methylquinoline

R Subashini ^a, Venkatesha R Hathwar ^b, P Nithya ^a, K Prabakaran ^a, F Nawaz Khan ^a,^*

PMCID: PMC2968224 PMID: 21582000

Abstract

In the title molecule, C₁₃H₁₅N₃O₂, the dihedral angle between the mean plane of the 1,3-dioxolane group and the 2-hydrazino-7-methylisoquinoline unit is 85.21 (5)°. The conformation of the molecule is influenced by bifurcated N—H⋯(O,O) and N—H⋯N intramolecular hydrogen bonds. In the crystal structure, molecules are linked via intermolecular N—H⋯O hydrogen bonds, forming extended chains along [001].

Related literature

For general background to hydrazine compounds, see: Broadhurst et al. (2001 ▶); Behrens (1999 ▶); Broadhurst (1991 ▶); Chao et al. (1999 ▶); Kametani (1968 ▶). For related crystal structures, see: Yang et al. (2008 ▶); Choudhury & Guru Row (2006 ▶); Choudhury et al. (2002 ▶); Hathwar et al. (2008 ▶); Cho et al. (2002 ▶); Manivel et al. (2009 ▶), and references therein. For bond-length data, see: Allen et al., 1987 ▶)

Experimental

Crystal data

C₁₃H₁₅N₃O₂
M _r = 245.28
Monoclinic,
a = 13.1909 (17) Å
b = 10.1165 (13) Å
c = 9.7805 (13) Å
β = 109.956 (2)°
V = 1226.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 290 (2) K
0.30 × 0.21 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.942, T _max = 0.987
8929 measured reflections
2279 independent reflections
1699 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.129
S = 1.06
2279 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003031/lh2748sup1.cif

e-65-0o407-sup1.cif^{(16.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003031/lh2748Isup2.hkl

e-65-0o407-Isup2.hkl^{(112.1KB, 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
N2—H2N⋯O1	0.843 (19)	2.372 (18)	2.9329 (17)	124.5 (15)
N2—H2N⋯O2	0.843 (19)	2.653 (18)	3.0968 (19)	114.3 (14)
N3—H3NA⋯N1	0.94 (2)	2.35 (2)	2.691 (2)	100.9 (15)
N3—H3NB⋯O2ⁱ	0.92 (2)	2.44 (2)	3.207 (2)	141.2 (19)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility setup under the IRHPA-DST program at IISc. We thank Professor T. N. Guru Row, IISc, Bangalore, for useful crystallographic discussions. FNK thanks the DST for Fast Track Proposal funding.

supplementary crystallographic information

Comment

The title compound (I), belongs to the quinoline class. Quinolines and quinolinones are an integral part of many naturally occurring fused heterocycles and find application in synthetic and pharmaceutical chemistry (Kametani, 1968). Isoquinolinones and isoquinolineamines have been reported as cancer chemotherapeutic agents (Behrens, 1999) whereas quinolyl and isoquinolyl derivatives have been reported as insecticidal compounds (Broadhurst, 1991). 3-substituted isoquinolines have potent use in medicine (Chao et al., 1999) and in general, hydrazine derivatives can be used as medicaments (Broadhurst et al., 2001; Choudhury, et al., 2002; Choudhury & Guru Row, 2006; Yang, et al., 2008). Due to the importance of quinoline derivates (Cho et al., 2002) and in continuous of our research on quinolines and isoquinoline derivatives (Hathwar et al., 2008; Manivel et al., 2009) we present here crystal structure of the title compound.

In (I) the dihedral angle between 1,3-dioxolane moiety and 2 hyrazino-7-methyl isoquinoline unit is 85.21 (5)°. All bond lengths (Allen et al., 1987) and angles are within normal ranges. The conformation of the molecule is influenced by N—H···O and N—H···N intramolecular hydrogen bonds whereas the crystal structure is stabilized by intermolecular N—H···O hydrogen bonds forming exteded chains along [001].

Experimental

A solution of 2-chloro (3-(1,3-dioxolan-2-yl)-7-methylquinoline in ethanol was treated with hydrazine hydrate and stirred at 323 K for 3hr. The product was filtered. The solid was washed with water and diethyl ether and dried under vacuum. Single crystals were obtained by recrystalization of (I) from DMSO.