(E)-N′-(4-Chloro­benzyl­idene)-2-meth­oxy­benzohydrazide

M Syukri Baharudin; Muhammad Taha; Nor Hadiani Ismail; Syed Adnan Ali Shah; Sammer Yousuf

doi:10.1107/S160053681300175X

. 2013 Jan 23;69(Pt 2):o276. doi: 10.1107/S160053681300175X

(E)-N′-(4-Chlorobenzylidene)-2-methoxybenzohydrazide

M Syukri Baharudin ^a, Muhammad Taha ^a, Nor Hadiani Ismail ^b, Syed Adnan Ali Shah ^a,^c, Sammer Yousuf ^d,^*

PMCID: PMC3569803 PMID: 23424549

Abstract

In the title hydrazone derivative, C₁₅H₁₃ClN₂O₂, the dihedral angle between the benzene rings is 2.36 (2)°. An intramolecular N—H⋯O hydrogen bond is present. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link the molecules into chains running parallel to the b axis.

Related literature

For applications and biological activity of hydrazone derivatives, see: Khan et al. (2011 ▶, 2012 ▶); Kūçūkgūzel et al. (1999 ▶); Patel et al. (1984 ▶); Wilder (1967 ▶); Glasser & Doughty (1962 ▶). For a related structure, see: Cao (2009 ▶). graphic file with name e-69-0o276-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₃ClN₂O₂
M _r = 288.72
Orthorhombic,
a = 12.5830 (7) Å
b = 9.8335 (5) Å
c = 23.6377 (13) Å
V = 2924.8 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 273 K
0.48 × 0.27 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.884, T _max = 0.974
16194 measured reflections
2713 independent reflections
2021 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.124
S = 1.06
2713 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(18.5KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681300175X/rz5038sup1.cif

e-69-0o276-sup1.cif^{(18.5KB, cif)}

Click here for additional data file.^{(133.3KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681300175X/rz5038Isup2.hkl

e-69-0o276-Isup2.hkl^{(133.3KB, hkl)}

Click here for additional data file.^{(2.1KB, cml)}

Supplementary material file. DOI: 10.1107/S160053681300175X/rz5038Isup3.cml

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—H1A⋯O2	0.76 (2)	2.04 (2)	2.632 (2)	135.7 (19)
N1—H1A⋯O1ⁱ	0.76 (2)	2.58 (2)	3.163 (3)	135.5 (19)
C8—H8A⋯O1ⁱ	0.93	2.42	3.127 (3)	132

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Organic compounds based on the hydrazone moiety are well known due to their wide range of applications both in structural and medicinal chemistry (Khan et al., 2011, 2012; Kūçūkgūzel et al., 1999; Patel et al., 1984; Wilder, 1967; Glasser & Doughty, 1962). The title compound is a hydrazone derivative synthesized in order to evaluate its biological activities.

The structure of title compound (Fig. 1) is similar to that of the previously published compound (E)-N'-(2-chlorobenzylidene)-2-methoxybenzohydrazide (Cao, 2009) with the difference that the 2-chlorobenzene ring is replaced by a 4-chlorobenzene ring (C9–19 C14). The bond lengths and angles were found to be similar to those observed in the structurally related phenyl hydrazone (Cao, 2009). The azomethine double bond adopts an E configuration (C═N, 1.270 (3) Å). The molecular conformation is stablized by an intramolecular N1—H1A···O2 hydrogen bond (Table 1) to generate an S6 graph set ring motif. N1—H1A···O1 and C8—H8A···O1 hydrogen bonds play important roles in stabilizing the crystal structure by forming chains running parallel to the b axis (Fig. 2).

Experimental

The title compound was synthesized by refluxing in methanol a mixture of 2-methoxybenzohydrazide (0.332 g, 2 mmol), 4-chlorobenzaldehyde (0.281 g, 2 mmol) and a catalytical amount of acetic acid for 3 h. The progress of reaction was monitored by TLC. After completion of the reaction, the solvent was evaporated by vacuum to afford the crude product which was further recrystallized in methanol to obtain colourless crystals (0.467 g, 81% yield). All chemicals were purchased by sigma Aldrich, Germany.