3-Hy­droxy-N′-[(E)-2-thienyl­methyl­idene]-2-naphtho­hydrazide

Qingkun Wu; Handong Yin; Daqi Wang

doi:10.1107/S160053681005405X

. 2011 Jan 8;67(Pt 2):o277. doi: 10.1107/S160053681005405X

3-Hydroxy-N′-[(E)-2-thienylmethylidene]-2-naphthohydrazide

Qingkun Wu ^a, Handong Yin ^a,^*, Daqi Wang ^a

PMCID: PMC3051446 PMID: 21522969

Abstract

The asymmetric unit of the title compound, C₁₆H₁₂N₂O₂S, contains three independent molecules. Intramolecular N—H⋯O hydrogen bonds in the three molecules lead to very similar conformations: the thiopene ring and naphthalene ring system in the three molecules form dihedral angles of 10.3 (2), 9.1 (2) and 9.3 (3)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into chains propagating in [031].

Related literature

For related structures, see: Huang (2009 ▶); Liang et al. (2008 ▶); Shafiq et al. (2009 ▶).

Experimental

Crystal data

C₁₆H₁₂N₂O₂S
M _r = 296.34
Orthorhombic,
a = 19.8191 (16) Å
b = 6.2487 (5) Å
c = 33.947 (3) Å
V = 4204.1 (6) Å³
Z = 12
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 K
0.41 × 0.17 × 0.06 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.909, T _max = 0.986
20887 measured reflections
7258 independent reflections
3449 reflections with I > 2σ(I)
R _int = 0.077

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.078
S = 0.97
7258 reflections
569 parameters
11 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ▶), 3473 Friedel pairs
Flack parameter: 0.01 (7)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S160053681005405X/cv5019sup1.cif

e-67-0o277-sup1.cif^{(31.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005405X/cv5019Isup2.hkl

e-67-0o277-Isup2.hkl^{(355.2KB, 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
O6—H51⋯O2	0.82	2.03	2.771 (5)	149
N6—H54⋯O6	0.86	1.96	2.641 (5)	135
N2—H2A⋯O4	0.86	1.96	2.660 (5)	138
N4—H53⋯O5	0.86	1.90	2.614 (5)	139
O5—H50⋯O1	0.82	1.87	2.682 (5)	169
O4—H4⋯O3ⁱ	0.82	2.40	2.688 (5)	102

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Symmetry code: (i) Inline graphic .

Acknowledgments

We acknowledge the National Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (grant No. Y2008B48) for financial support.

supplementary crystallographic information

Comment

In continuation of our research of organotin derivatives, the title compound (I) - a novel Schiff base - have been synthesized. Herewith we present its crystal structure.

In (I), there are three independent molecules in the asymmetric unit (Fig. 1). All the bond lengths and angles are normal and correspond to those observed in the related compounds (Huang (2009); Liang et al. (2008); Shafiq et al. (2009). Intramolecular N—H···O hydrogen bonds (Table 1) lead to very close conformations - the thiopene ring and naphthalene bicycle in three molecules form dihedral angles of 9.67 (27)°, 9.16 (29)° and 9.41 (26)°, respectively.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into chains propagated in direction [031].

Experimental

The methanol solution of thiophene(0.1 mol) was added dropwise to a solution of 3-hydroxyl-2-naphthohydrazide(0.1 mol) in mehtanol. Then the mixture was stirred at room temperature for 6 h, during which time a yellow precipitate can be observed. The mixture was filtrated and the obtained solid was recrystallized from methanol. Yield 80%. M.p. 245°C. Anal. Calcd (%) for C₁₆H₁₂N₂O₂S (Mr = 296.34): C, 64.84; H, 4.08; N, 9.45. Found (%): C, 64.82; H, 4.03; N, 9.49.