1-[1-(4-Chloro­phen­yl)ethyl­idene]carbono­hydrazide

Lingyun Du; Lei Du; Shuhao Wang

doi:10.1107/S1600536809030384

. 2009 Aug 12;65(Pt 9):o2130. doi: 10.1107/S1600536809030384

1-[1-(4-Chlorophenyl)ethylidene]carbonohydrazide

Lingyun Du ^a,^*, Lei Du ^a, Shuhao Wang ^a

PMCID: PMC2969952 PMID: 21577542

Abstract

The molecular skeleton of the title molecule, C₉H₁₁ClN₄O, is essentially planar, the dihedral angle between the ring and the and N/N/C plane being 6.7 (3)°. In the crystal, intermolecular N—H⋯O and N—H⋯N hydrogen bonds link the molecules into ribbons propagated along [010].

Related literature

For the biological activity of carbonohydrazide derivatives, see: Loncle et al. (2004 ▶). For related structures, see Meyers et al. (1995 ▶).

Experimental

Crystal data

C₉H₁₁ClN₄O
M _r = 226.67
Monoclinic,
a = 14.6429 (14) Å
b = 9.6041 (12) Å
c = 7.4327 (9) Å
β = 90.102 (1)°
V = 1045.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 298 K
0.40 × 0.30 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.875, T _max = 0.960
4419 measured reflections
1837 independent reflections
1085 reflections with I > 2σ(I)
R _int = 0.037

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.126
S = 1.01
1837 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030384/cv2587sup1.cif

e-65-o2130-sup1.cif^{(14.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030384/cv2587Isup2.hkl

e-65-o2130-Isup2.hkl^{(90.5KB, 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⋯N4ⁱ	0.86	2.24	3.024 (3)	152
N3—H3⋯O1ⁱⁱ	0.86	2.09	2.850 (3)	147
N4—H4A⋯O1ⁱⁱⁱ	0.89	2.34	3.206 (3)	164

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

Acknowledgments

The authors acknowledge financial support by the Science Foundation of China (grant No. 20877037).

supplementary crystallographic information

Comment

A number of carbonohydrazide derivatives have been claimed to possess a bioactivity such as antibacterial, antifungal, anticonvulsant and anticancer activities (Loncle et al., 2004). We describe in this paper a user-friendly, solvent-free protocol for the synthesis of substituted carbonohydrazide starting from the fragrant ketones and carbohydrazide under solvent-free conditions in this paper. Using this method, which can be considered as a a general method for the synthesis of substituted carbonohydrazides, we obtained the title compound, (I). We present here its crystal structure.

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in bis(3-fluorophenylmethine)carbonohydrazide (Meyers et al., 1995). The N4/N3/C1 and N2/N1/C1 planes form a dihedral angle of 4.09 (4)°, while ring C4-C9 and N2/N1/C1 plane form a dihedral angle of 2.64 (29)°.

In the crystal, intermolecular N—H···O and N—H···N hydrogen bonds (Table 1) link the molecules into ribbons propagated in direction [010].

Experimental

p-Chloroacetophenone (5.0 mmol) and carbohydrazide (5.0 mmol) were mixed in 50 ml flash under sovlent-free condtions After stirring 3 h at 373 K, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₉H₁₁ClN₄O: C 47.69, H 4.89, N 24.72%; found: C 47.63, H 4.75, N 24.64%.