2-Hydr­oxy-N′-[(E)-(3-hydr­oxy-2-naphth­yl)methyl­ene]benzohydrazide

Yuying Sun; Hong-Gang Li; Xiao Wang; Shizhou Fu; Daqi Wang

doi:10.1107/S1600536808044073

. 2009 Jan 8;65(Pt 2):o262. doi: 10.1107/S1600536808044073

2-Hydroxy-N′-[(E)-(3-hydroxy-2-naphthyl)methylene]benzohydrazide

Yuying Sun ^a, Hong-Gang Li ^b, Xiao Wang ^c, Shizhou Fu ^c, Daqi Wang ^c,^*

PMCID: PMC2968222 PMID: 21581877

Abstract

In the title molecule, C₁₈H₁₄N₂O₃, O—H⋯N and N—H⋯O hydrogen bonds influence the molecular conformation; the benzene and naphthalene planes are inclined at a dihedral angle of 11.54 (5)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into chains running in the [01 Inline graphic ] direction.

Related literature

For useful applications of salicyloyl hydrazide derivatives, see: Sumita et al. (1999 ▶). For the crystal structure of (E)-2-hydroxy-N′-(3-hydroxy-4-methoxybenzylidene)benzohydrazide, see: Luo (2007 ▶).

Experimental

Crystal data

C₁₈H₁₄N₂O₃
M _r = 306.31
Orthorhombic,
a = 21.124 (2) Å
b = 11.6212 (13) Å
c = 5.9826 (8) Å
V = 1468.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.32 × 0.18 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.970, T _max = 0.986
6099 measured reflections
1422 independent reflections
896 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.076
S = 1.04
1422 reflections
209 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 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/S1600536808044073/cv2501sup1.cif

e-65-0o262-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808044073/cv2501Isup2.hkl

e-65-0o262-Isup2.hkl^{(70.2KB, 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
O3—H3⋯N2	0.82	1.90	2.623 (5)	146
N1—H1⋯O2	0.86	1.92	2.620 (4)	137
O2—H2⋯O1ⁱ	0.82	1.81	2.573 (4)	155

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (grant No. X051040).

supplementary crystallographic information

Comment

Salicyloyl hydrazide is an important organic intermediate, it can act as moulding board in inorganic complex (Sumita et al., 1999). In this paper, we present the title compound (I), which was synthesized by the reaction of 2-hydroxyl naphthaldehyde and salicyloyl hydrazide.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the reported compound (Luo, 2007). In the crystal structure, the C8=N2 bond length is 1.279 (5) Å showing the double-bond character. The dihedral angle between the naphthalene ring and C8/N2/N1 is 10.14 (3) Å, the C1/N1/N2 and benzene ring form a dihedral angle of 6.70 (4) Å showing that intramolecular O—H···N and N—H···O hydrogen bonds (Table 1) influence the molecular conformation.

In the crystal, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into chains running in direction [01–1].

Experimental

Salicyloyl hydrazide (0.5 mmol) and freshly 2-hydroxyl naphthaldehyde (0.5 mmol) were mixed in 50 ml flash. After stirring 30 min at 353 K, the mixture then cooling slowly to room temperature and affording the title compound, then recrystallized from ethanol, affording the title compound as a green crystalline solid. Elemental analysis: calculated for C₁₈H₁₄N₂O₃: C 70.58, H 4.61, N 9.15%; found: C 70.53, H 4.55, N 9.24%.