(E)-4-Amino-N′-(2-hy­droxy-5-methyl­benzyl­idene)benzohydrazide

Hadi Kargar; Reza Kia; Muhammad Nawaz Tahir

doi:10.1107/S1600536812027948

. 2012 Jun 23;68(Pt 7):o2185–o2186. doi: 10.1107/S1600536812027948

(E)-4-Amino-N′-(2-hydroxy-5-methylbenzylidene)benzohydrazide

Hadi Kargar ^a,^*, Reza Kia ^b,^‡, Muhammad Nawaz Tahir ^c,^*

PMCID: PMC3393987 PMID: 22798852

Abstract

The asymmetric unit of the title compound, C₁₅H₁₅N₃O₂, comprises two crystallographically independent molecules (A and B), each having an E conformation around the C=N bond. In each molecule, there is an intramolecular O—H⋯N hydrogen bond making an S(6) ring motif. The dihedral angles between the substituted phenyl rings are 17.49 (9) and 10.03 (9)°. In the crystal, N—H⋯O hydrogen bonds link neighbouring independent molecules into infinite chains, of the type –A–B–A–B–, along the a axis, enclosing R ₂ ¹(7) ring motifs. The chains are linked by N—H⋯O hydrogen bonds and C—H⋯O interactions, leading to the formation of a three-dimensional network.

Related literature

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006 ▶); Karthikeyan et al. (2006 ▶). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012 ▶); Shi & Li (2012 ▶); Bakir & Green (2002 ▶); Kargar et al. (2012a ▶,b ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₅N₃O₂
M _r = 269.30
Triclinic,
a = 10.2717 (8) Å
b = 11.5668 (10) Å
c = 11.9152 (9) Å
α = 94.544 (3)°
β = 100.583 (3)°
γ = 95.880 (3)°
V = 1377.28 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 291 K
0.30 × 0.25 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.974, T _max = 0.979
21355 measured reflections
6081 independent reflections
3917 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.137
S = 1.05
6081 reflections
365 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027948/su2458sup1.cif

e-68-o2185-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027948/su2458Isup2.hkl

e-68-o2185-Isup2.hkl^{(297.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812027948/su2458Isup3.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
O2—H2⋯N3	0.82	1.89	2.6079 (19)	145
O4—H4⋯N6	0.82	1.86	2.5826 (17)	146
N2—H1N2⋯O4ⁱ	0.94	2.01	2.9342 (18)	169
N5—H1N5⋯O1ⁱⁱ	0.95	1.93	2.8615 (17)	167
N1—H1A⋯O3ⁱⁱⁱ	0.86	2.42	3.149 (2)	142
C12—H12A⋯O3^iv	0.93	2.51	3.400 (2)	160
C17—H17A⋯O1ⁱⁱ	0.93	2.53	3.320 (2)	143

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

Acknowledgments

HK thanks PNU for financial support. MNT thanks GC University of Sargodha, Pakistan, for the research facility.

supplementary crystallographic information

Comment

Schiff bases are one of the most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and magnetism, and supramolecular architectures (Karthikeyan et al., 2006; Kucukguzel et al., 2006). Structures of Schiff bases derived from substituted 4-aminobenzohydrazide have been reported earlier (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002; Kargar et al. (2012a,b). In order to explore the structure of new Schiff base derivatives, the title compound was prepared and characterized crystallographically.

The asymmetric unit of the title compound, Fig. 1, comprises two crystallographically independent molecules (A and B) both with an E conformation around the C═N bond. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those reported for related structures (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002; Kargar et al. (2012a,b). In each molecule there is an intramolecular O—H···N hydrogen bond making an S(6) ring motif. The dihedral angles between the substituted phenyl rings (C1-C6/C9-C14 in molecule A and C16-C21/C24-C29 in molecule B) are 17.49 (9) and 10.03 (9)°, respectively.

In the crystal, N—H···O hydrogen bonds (Table 1 and Fig. 2) link neighbouring independent molecules into infinite chains, of the type -A-B-A-B-, along the a axis, enclosing R¹₂(7) ring motifs (Bernstein et al., 1995). The chains are linked by N-H···O hydrogen bonds and C—H···O interactions leading to the formation of a three-dimensional network (Table 1).

Experimental

The title compound was synthesized by adding 1 mmol of methyl 4-aminobenzoate to a solution of 5-methylsalicylaldehyde (1 mmol) in methanol (30 ml). The mixture was refluxed with stirring for 30 min and after cooling to room temperature a light-yellow precipitate was filtered and washed with diethylether and dried in air. Yellow prismatic crystals of the title compound, suitable for X-ray structure analysis, were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.