1-(3-Phenyl­isoquinolin-1-yl)hydrazine

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

doi:10.1107/S1600536808042062

. 2008 Dec 17;65(Pt 1):o137–o138. doi: 10.1107/S1600536808042062

1-(3-Phenylisoquinolin-1-yl)hydrazine

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

PMCID: PMC2968055 PMID: 21581597

Abstract

The title compound, C₁₅H₁₃N₃, contains two independent molecules in the asymmetric unit. The isoquinoline moiety and phenyl rings form dihedral angles of 4.38 (2) and 10.14 (3)° in the two independent molecules. The crystal packing is stabilized by N—H⋯N molecular dimers formed across a center of symmetry.

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 ▶). For bond-length data, see: Allen et al. (1998 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₃N₃
M _r = 235.28
Triclinic,
a = 6.672 (2) Å
b = 13.825 (4) Å
c = 14.934 (5) Å
α = 63.836 (5)°
β = 86.895 (6)°
γ = 82.106 (5)°
V = 1224.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 (2) K
0.15 × 0.12 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.953, T _max = 0.996
12381 measured reflections
4546 independent reflections
2926 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.116
S = 1.02
4546 reflections
429 parameters
All H-atom parameters refined
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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 (Farrugia,1999 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042062/cs2101sup1.cif

e-65-0o137-sup1.cif^{(24.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042062/cs2101Isup2.hkl

e-65-0o137-Isup2.hkl^{(227.1KB, 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′—H2′N⋯N3′ⁱ	0.91 (2)	2.15 (2)	2.967 (2)	151 (2)
N2—H2N⋯N3ⁱⁱ	0.90 (2)	2.20 (2)	3.027 (2)	152 (2)
N3′—H3′B⋯N1′ⁱⁱⁱ	0.89 (2)	2.24 (2)	3.119 (2)	169 (2)
N3—H3A⋯N1^iv	0.92 (2)	2.26 (2)	3.170 (3)	168 (2)

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

Acknowledgments

We thank the Department of Science and Technology, India, for use of the CCD facility set up under the IRHPA–DST program at IISc. We thank Prof 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 belongs to the class isoquinolines. Isoquinolines and isoquinolinones are an integral part of many naturally occurring fused heterocycles and find applications in synthetic and pharmaceutical chemistry (Kametani et al., 1968). Isoquinolinones and isoquinoline amines were reported as cancer chemotherapeutic agents (Behrens, 1999) whereas quinolyl and isoquinolyl derivatives have been reported as insecticidal compounds (Broadhurst, 1991). 3-Substituted isoquinolines are of 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, 2006) reported crystal structures of substituted isoquinolines while Hathwar, et al. (2008) reports the crystal structure of an isoquinolinyl diselenide.

The asymmetric unit of the crystal structure of the title compound contains two independent molecules (Fig. 1). The isoquinoline moiety and phenyl rings form dihedral angles of 4.38 (2) and 10.14 (3)° ,respectively, in the two independent molecules. All bond lengths and angles are normal (Allen et al., 1998). The packing (Fig. 2) is consolidated by four N—H···N hydrogen bonds. All the four N—H···N hydrogen bonds generate dimers across centres of symmetry (Table 1) resulting in tight molecular packing in the crystal. The N2'-H2'N···N3' and the N2—H2N···N3 hydrogen bonds form a R²₂(6) motif whereas the N3'-H3'B···N1' and the N3—H3A···N1 hydrogen bond dimers form a R²₂(10) motif (Bernstein et al., 1995) in the crystal (Fig. 2).

Experimental

The solution of 1-chloro-3-phenylisoquioline 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 of the title compound were obtained via recrystalization from a dichloromethane solution.