Dieth­yl[N-(3-meth­oxy-2-oxidobenzyl­idene)-N′-(oxidomethyl­ene)hydrazine-κ3 O,N,O′]tin(IV)

Shaukat Shuja; M Nawaz Tahir; Saqib Ali; Nasir Khalid

doi:10.1107/S1600536808018953

. 2008 Jun 28;64(Pt 7):m963–m964. doi: 10.1107/S1600536808018953

Diethyl[N-(3-methoxy-2-oxidobenzylidene)-N′-(oxidomethylene)hydrazine-κ³ O,N,O′]tin(IV)

Shaukat Shuja ^a, M Nawaz Tahir ^b,^*, Saqib Ali ^a, Nasir Khalid ^c

PMCID: PMC2961818 PMID: 21202810

Abstract

In the molecule of the title compound, [Sn(C₂H₅)₂(C₉H₈N₂O₃)], the Sn atom is five-coordinated in a distorted trigonal-bipyramidal configuration by two O and one N atoms of the tridentate Schiff base ligand in the equatorial plane, and by two C atoms of ethyl groups in the axial positions. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For related literature, see: Chen et al. (2006 ▶); Shuja et al. (2007a ▶,b ▶,c ▶); Shuja et al. (2008 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

[Sn(C₂H₅)₂(C₉H₈N₂O₃)]
M _r = 368.98
Triclinic,
a = 8.2485 (3) Å
b = 9.8609 (4) Å
c = 10.4501 (4) Å
α = 63.521 (2)°
β = 68.967 (1)°
γ = 77.803 (2)°
V = 708.79 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.81 mm⁻¹
T = 296 (2) K
0.30 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.650, T _max = 0.720
14275 measured reflections
3603 independent reflections
3458 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.016
wR(F ²) = 0.063
S = 1.02
3603 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808018953/hk2477sup1.cif

e-64-0m963-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018953/hk2477Isup2.hkl

e-64-0m963-Isup2.hkl^{(173.1KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Selected geometric parameters (Å, °).

Sn1—C11	2.1216 (19)
Sn1—C9	2.1217 (18)
Sn1—O1	2.1888 (13)
Sn1—O2	2.2162 (14)
Sn1—N1	2.2271 (15)

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C11—Sn1—C9	153.45 (9)
C11—Sn1—O1	97.19 (7)
C9—Sn1—O1	93.40 (7)
C11—Sn1—O2	92.71 (8)
C9—Sn1—O2	88.78 (7)
O1—Sn1—O2	152.79 (5)
C11—Sn1—N1	99.42 (7)
C9—Sn1—N1	106.13 (7)
O1—Sn1—N1	82.07 (5)
O2—Sn1—N1	71.30 (6)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O2ⁱ	0.96	2.34	3.068 (4)	132

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore, and for financial support to SS for PhD studies under the Indigenous Scholarship Scheme (PIN Code: 042–111889).

supplementary crystallographic information

Comment

In continuation of our efforts to synthesize various Schiff base ligands of substituted salicylaldehydes with hydrazides, aminoacids and their organotin derivatives (Shuja et al., 2007a,b,c; Shuja et al., 2008), we report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the Sn atom is five-coordinated in distorted trigonal bipyramidal configuration (Table 1) by two O and one N atoms of the tridentate Schiff base ligand in the equatorial plane, and two C atoms of diethyl groups in the axial positions. The bond lengths and angles are within normal ranges, which are comparable with the corresponding values in (3-methoxy-2-oxidobenzaldehyde benzoylhydrazonato)dimethyltin(IV), (II) (Chen et al., 2006) and (2,2'-bipyridine-κ²N,N'){[(3-methoxy-2-oxidobenzylidene -κO²)hydrazono]methanolato-κ²N²,O}dimethyltin(IV), (III) (Shuja et al., 2008). The Sn1-C9 [2.1217 (18) Å] and Sn1-C11 [2.1219 (19) Å] bonds in (I) are reported as 2.099 (4) and 2.102 (4) Å in (II) and 2.097 (3) and 2.098 (3) Å in (III). On the other hand, the Sn1-O1 [2.1888 (13) Å] and Sn1-O2 [2.2162 (14) Å] bonds in (I) are reported as 2.131 (3) and 2.178 (3) Å in (II) and 2.1572 (14) and 2.2658 (15) Å in (III), while the Sn1-N1 [2.2271 (15) Å] bond in (I) is reported as 2.188 (3) Å in (II) and 2.2980 (18) Å in (III).

Rings A (Sn1/O2/N1/N2/C8) and C (C1-C6) are, of course, planar, and the dihedral angle between them is A/C = 7.96 (3)°. Ring B (Sn1/O1/N1/C1/C6/C7) adopts flattened-boat [φ = -57.24 (2)° and θ = 107.39 (3)°] conformation, having total puckering amplitude, Q_T, of 0.453 (3) Å (Cremer & Pople, 1975).

In the crystal structure, intermolecular C-H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, N-(3-methoxy-2-hydroxybenzylidene)- formichydrazide (0.58 g, 3.0 mmol) and Et₃N (0.84 ml, 6 mmol) were added to dry toluene (100 ml) in a 250 ml round bottom flask equipped with a reflux condenser. Diethyltin(IV) dichloride (0.74 g, 3.0 mmol) dissolved in dry toluene (20 ml) was then added. The reaction mixture was stirred at room temperature for 5 h and allowed to stand overnight. The formed Et₃N-HCl was filtered off and the clear yellow solution was evaporated on a rotary evaporator under reduced pressure. Crystals of (I) were obtained by recrystallization from a chloroform solution.