1,5-Bis(2-chloro­benzyl­idene)carbonohydrazide

Kaozhen Li; Jing Jiao; Yong Wang; Guo-Dong Wei; Daqi Wang

doi:10.1107/S1600536809026014

. 2009 Jul 11;65(Pt 8):o1846. doi: 10.1107/S1600536809026014

1,5-Bis(2-chlorobenzylidene)carbonohydrazide

Kaozhen Li ^a,^*, Jing Jiao ^a, Yong Wang ^b, Guo-Dong Wei ^c, Daqi Wang ^a

PMCID: PMC2977268 PMID: 21583546

Abstract

In the title molecule, C₁₅H₁₂Cl₂N₄O, the two benzene rings are inclined at a dihedral angle of 14.5 (2)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link molecules into chains propagated in [001].

Related literature

For related structures, see: Meyers et al. (1995 ▶); Li et al. (2008 ▶).

Experimental

Crystal data

C₁₅H₁₂Cl₂N₄O
M _r = 335.19
Monoclinic,
a = 10.7889 (11) Å
b = 15.7117 (19) Å
c = 9.0543 (10) Å
β = 90.978 (1)°
V = 1534.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 298 K
0.49 × 0.43 × 0.42 mm

Data collection

Bruker SMART APEX CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.817, T _max = 0.840
7395 measured reflections
2684 independent reflections
1698 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.063
wR(F ²) = 0.186
S = 1.05
2684 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.29 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/S1600536809026014/cv2581sup1.cif

e-65-o1846-sup1.cif^{(16.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026014/cv2581Isup2.hkl

e-65-o1846-Isup2.hkl^{(131.8KB, 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⋯O1ⁱ	0.86	2.15	2.925 (4)	149
N3—H3⋯O1ⁱ	0.86	2.06	2.863 (4)	154

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge financial support by the University Student Science and Technology Culture Foundation of Liaocheng University (grant No. SRT08040HX2).

supplementary crystallographic information

Comment

In continuation of our ongoing program directed to the development of environmentally benign methods of chemical synthesis (Li et al., 2008), we present here a user-friendly, solvent-free protocol for the synthesis of substituted carbonohydrazide starting from the fragrant aldehydes and carbohydrazide under solvent-free conditions. Using this method, we obtained the title compound, (I).

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). Two benzene rings - C3-C8 and C10-C15, respectively - form a dihedral angle of 14.46 (22)°. Intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains propagated in direction [001].

Experimental

o-Chlorobenzaldehyde (10 mmol) and carbohydrazide (5.0 mmol) were mixed in 50 ml flash under sovlent-free condtions After stirring 2 h at 373 K, tthe resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C₁₅H₁₂Cl₂N₄O: C 53.75, H 3.61, N 16.72%; found: C 53.61, H 3.47, N 16.86%.