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Acta Cryst. (2009). E65, m816    [ doi:10.1107/S1600536809022259 ]

[N'-(5-Chloro-2-oxidobenzylidene-[kappa]O)-3-hydroxy-2-naphthohydrazidato-[kappa]2N',O]dimethyltin(IV)

S. M. Lee, K. M. Lo, H. Mohd Ali and S. W. Ng

Abstract top

The SnIV atom in the title compound, [Sn(CH3)2(C18H11ClN2O3)], shows a trans-C2NO2Sn trigonal-bipyramidal coordination; the axial O-Sn-O angle is 155.22 (5)°. The tridentate N'-(5-chloro-2-oxidobenzylidene)-3-hydroxy-2-naphthohydrazidate dianion is stabilized by an intramolecular O-H...N hydrogen bond.

Related literature top

The dianions of similar N'-(2-hydroxybenzylidene)benzohydrazones O,N,O'-chelate tin in organotin compounds; see: Labib et al. (1996); Samanta et al. (2007).

Experimental top

The Schiff base was synthesized by the condensation of 3-hydroxy-2-naphthoylhydrazide and 5-chorosalicylaldehyde. The Schiff base (0.50 g, 1.5 mmol) and dimethyltin oxide (0.24 g, 1.5 mmol) were heated in methanol until the oxide dissolved completely; the filtered solution yielded yellow crystals when the solvent was allowed to evaporate over a few days.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5Ueq(C). The hydroxy H-atom was refined with a distance restraint of 0.84±0.01 Å.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of (CH3)2Sn(C18H11N2O3) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
[N'-(5-Chloro-2-oxidobenzylidene-κO)-3-hydroxy- 2-naphthohydrazidato-κ2N',O]dimethyltin(IV) top
Crystal data top
[Sn(CH3)2(C18H11ClN2O3)]Z = 2
Mr = 487.50F(000) = 484
Triclinic, P1Dx = 1.772 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8374 (1) ÅCell parameters from 6181 reflections
b = 11.6207 (2) Åθ = 2.5–28.3°
c = 12.0159 (2) ŵ = 1.57 mm−1
α = 86.874 (1)°T = 100 K
β = 75.926 (1)°Block, yellow
γ = 80.635 (1)°0.30 × 0.20 × 0.10 mm
V = 913.61 (3) Å3
Data collection top
Bruker SMART APEX
diffractometer		4182 independent reflections
Radiation source: fine-focus sealed tube3924 reflections with I > 2σ(I)
graphiteRint = 0.015
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −8→8
Tmin = 0.623, Tmax = 0.746k = −14→15
8585 measured reflectionsl = −15→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.019Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0261P)2 + 0.3698P]
where P = (Fo2 + 2Fc2)/3
4182 reflections(Δ/σ)max = 0.001
250 parametersΔρmax = 0.65 e Å−3
1 restraintΔρmin = −0.58 e Å−3
Crystal data top
[Sn(CH3)2(C18H11ClN2O3)]γ = 80.635 (1)°
Mr = 487.50V = 913.61 (3) Å3
Triclinic, P1Z = 2
a = 6.8374 (1) ÅMo Kα radiation
b = 11.6207 (2) ŵ = 1.57 mm−1
c = 12.0159 (2) ÅT = 100 K
α = 86.874 (1)°0.30 × 0.20 × 0.10 mm
β = 75.926 (1)°
Data collection top
Bruker SMART APEX
diffractometer		4182 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3924 reflections with I > 2σ(I)
Tmin = 0.623, Tmax = 0.746Rint = 0.015
8585 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.019H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.049Δρmax = 0.65 e Å−3
S = 1.04Δρmin = −0.58 e Å−3
4182 reflectionsAbsolute structure: ?
250 parametersFlack parameter: ?
1 restraintRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.249480 (17)0.940034 (10)0.829046 (10)0.01557 (5)
Cl10.43674 (7)1.55715 (4)0.85417 (4)0.02564 (11)
O10.1479 (2)1.10418 (11)0.90330 (12)0.0216 (3)
O20.4251 (2)0.81921 (11)0.69992 (12)0.0232 (3)
O30.8870 (2)0.93252 (12)0.43301 (12)0.0248 (3)
H30.813 (3)0.968 (2)0.4896 (15)0.033 (7)*
N10.4700 (2)1.03357 (13)0.71084 (13)0.0155 (3)
N20.6016 (2)0.96863 (13)0.62100 (13)0.0164 (3)
C1−0.0334 (3)0.92182 (17)0.79696 (17)0.0219 (4)
H1A−0.14000.93310.86830.033*
H1B−0.02550.84360.76800.033*
H1C−0.06630.98030.73970.033*
C20.3785 (3)0.85984 (17)0.96219 (17)0.0235 (4)
H2A0.27420.86571.03470.035*
H2B0.49130.89910.96910.035*
H2C0.42990.77750.94450.035*
C30.2252 (3)1.20273 (15)0.89032 (16)0.0168 (3)
C40.1378 (3)1.29089 (16)0.97140 (16)0.0196 (4)
H40.02741.27751.03350.023*
C50.2091 (3)1.39631 (16)0.96262 (16)0.0195 (4)
H50.15201.45331.02010.023*
C60.3645 (3)1.41882 (15)0.86956 (16)0.0188 (4)
C70.4554 (3)1.33520 (16)0.78900 (16)0.0179 (4)
H70.56231.35140.72600.021*
C80.3901 (3)1.22474 (15)0.79955 (15)0.0158 (3)
C90.4990 (3)1.14094 (15)0.71396 (15)0.0160 (3)
H90.60201.16650.65390.019*
C100.5659 (3)0.86010 (15)0.62363 (15)0.0162 (3)
C110.6967 (3)0.78165 (15)0.53296 (15)0.0154 (3)
C120.8488 (3)0.82057 (15)0.44149 (16)0.0173 (3)
C130.9604 (3)0.74493 (16)0.35706 (15)0.0178 (4)
H131.05870.77230.29550.021*
C140.9313 (3)0.62645 (16)0.36032 (15)0.0164 (3)
C151.0449 (3)0.54640 (16)0.27417 (15)0.0188 (4)
H151.14140.57230.21070.023*
C161.0161 (3)0.43211 (17)0.28209 (16)0.0206 (4)
H161.09410.37940.22430.025*
C170.8725 (3)0.39148 (16)0.37463 (17)0.0208 (4)
H170.85340.31200.37870.025*
C180.7606 (3)0.46675 (16)0.45860 (16)0.0181 (4)
H180.66470.43900.52120.022*
C190.7861 (3)0.58623 (15)0.45330 (15)0.0161 (3)
C200.6700 (3)0.66597 (15)0.53765 (15)0.0159 (3)
H200.57080.63950.59930.019*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01565 (7)0.01387 (7)0.01579 (7)−0.00315 (4)−0.00023 (5)−0.00126 (4)
Cl10.0265 (2)0.0153 (2)0.0333 (3)−0.00562 (17)−0.0009 (2)−0.00611 (18)
O10.0212 (7)0.0156 (6)0.0240 (7)−0.0042 (5)0.0037 (5)−0.0026 (5)
O20.0250 (7)0.0166 (7)0.0237 (7)−0.0071 (5)0.0057 (6)−0.0045 (5)
O30.0301 (8)0.0177 (7)0.0224 (7)−0.0094 (6)0.0066 (6)−0.0051 (5)
N10.0150 (7)0.0161 (7)0.0144 (7)−0.0019 (6)−0.0017 (6)−0.0022 (6)
N20.0166 (7)0.0159 (7)0.0150 (7)−0.0024 (6)0.0001 (6)−0.0035 (6)
C10.0196 (9)0.0252 (10)0.0209 (9)−0.0074 (7)−0.0026 (7)0.0010 (7)
C20.0263 (10)0.0207 (9)0.0238 (10)−0.0013 (8)−0.0079 (8)−0.0008 (7)
C30.0166 (8)0.0149 (8)0.0190 (9)−0.0012 (6)−0.0050 (7)−0.0004 (7)
C40.0189 (9)0.0195 (9)0.0174 (9)−0.0003 (7)−0.0005 (7)−0.0009 (7)
C50.0200 (9)0.0166 (9)0.0205 (9)0.0032 (7)−0.0052 (7)−0.0045 (7)
C60.0214 (9)0.0130 (8)0.0229 (9)−0.0027 (7)−0.0067 (7)−0.0019 (7)
C70.0167 (8)0.0184 (9)0.0184 (9)−0.0032 (7)−0.0033 (7)−0.0006 (7)
C80.0170 (8)0.0140 (8)0.0163 (8)−0.0006 (6)−0.0048 (7)−0.0017 (6)
C90.0158 (8)0.0160 (8)0.0159 (8)−0.0032 (6)−0.0027 (7)0.0003 (6)
C100.0161 (8)0.0169 (9)0.0155 (8)−0.0025 (7)−0.0032 (7)−0.0008 (7)
C110.0143 (8)0.0162 (8)0.0157 (8)−0.0018 (6)−0.0037 (7)−0.0021 (6)
C120.0192 (9)0.0155 (8)0.0177 (9)−0.0041 (7)−0.0044 (7)0.0000 (7)
C130.0168 (8)0.0208 (9)0.0150 (8)−0.0048 (7)−0.0010 (7)−0.0003 (7)
C140.0149 (8)0.0200 (9)0.0150 (8)−0.0015 (7)−0.0051 (7)−0.0027 (7)
C150.0181 (9)0.0228 (9)0.0145 (9)−0.0018 (7)−0.0022 (7)−0.0029 (7)
C160.0215 (9)0.0214 (9)0.0187 (9)−0.0002 (7)−0.0048 (7)−0.0069 (7)
C170.0213 (9)0.0161 (9)0.0260 (10)−0.0026 (7)−0.0072 (8)−0.0030 (7)
C180.0168 (8)0.0184 (9)0.0191 (9)−0.0028 (7)−0.0042 (7)−0.0011 (7)
C190.0149 (8)0.0174 (9)0.0166 (8)−0.0017 (7)−0.0049 (7)−0.0024 (7)
C200.0148 (8)0.0169 (9)0.0149 (8)−0.0028 (6)−0.0014 (7)−0.0015 (6)
Geometric parameters (Å, °) top
Sn1—O12.091 (1)C5—H50.9500
Sn1—O22.146 (1)C6—C71.371 (2)
Sn1—N12.190 (2)C7—C81.416 (2)
Sn1—C12.107 (2)C7—H70.9500
Sn1—C22.113 (2)C8—C91.436 (2)
Cl1—C61.745 (2)C9—H90.9500
O1—C31.324 (2)C10—C111.479 (2)
O2—C101.291 (2)C11—C201.382 (2)
O3—C121.362 (2)C11—C121.427 (2)
O3—H30.828 (10)C12—C131.374 (2)
N1—C91.299 (2)C13—C141.420 (3)
N1—N21.393 (2)C13—H130.9500
N2—C101.320 (2)C14—C191.417 (3)
C1—H1A0.9800C14—C151.421 (2)
C1—H1B0.9800C15—C161.369 (3)
C1—H1C0.9800C15—H150.9500
C2—H2A0.9800C16—C171.409 (3)
C2—H2B0.9800C16—H160.9500
C2—H2C0.9800C17—C181.368 (3)
C3—C81.411 (3)C17—H170.9500
C3—C41.408 (2)C18—C191.423 (3)
C4—C51.380 (3)C18—H180.9500
C4—H40.9500C19—C201.410 (2)
C5—C61.389 (3)C20—H200.9500
O1—Sn1—C195.03 (7)C6—C7—H7120.0
O1—Sn1—C297.04 (7)C8—C7—H7120.0
C1—Sn1—C2127.30 (8)C3—C8—C7119.79 (16)
O1—Sn1—O2155.22 (5)C3—C8—C9123.84 (16)
C1—Sn1—O294.59 (7)C7—C8—C9116.37 (16)
C2—Sn1—O295.16 (7)N1—C9—C8126.20 (16)
O1—Sn1—N182.77 (5)N1—C9—H9116.9
C1—Sn1—N1122.40 (7)C8—C9—H9116.9
C2—Sn1—N1109.96 (7)O2—C10—N2124.04 (16)
O2—Sn1—N172.80 (5)O2—C10—C11118.68 (15)
C3—O1—Sn1133.18 (12)N2—C10—C11117.28 (16)
C10—O2—Sn1115.30 (11)C20—C11—C12118.99 (16)
C12—O3—H3108.0 (18)C20—C11—C10118.33 (16)
C9—N1—N2114.99 (15)C12—C11—C10122.69 (16)
C9—N1—Sn1129.10 (12)O3—C12—C13117.62 (16)
N2—N1—Sn1115.88 (11)O3—C12—C11122.19 (16)
C10—N2—N1111.96 (14)C13—C12—C11120.18 (16)
Sn1—C1—H1A109.5C12—C13—C14121.08 (17)
Sn1—C1—H1B109.5C12—C13—H13119.5
H1A—C1—H1B109.5C14—C13—H13119.5
Sn1—C1—H1C109.5C19—C14—C15118.84 (16)
H1A—C1—H1C109.5C19—C14—C13118.96 (16)
H1B—C1—H1C109.5C15—C14—C13122.20 (17)
Sn1—C2—H2A109.5C16—C15—C14120.38 (17)
Sn1—C2—H2B109.5C16—C15—H15119.8
H2A—C2—H2B109.5C14—C15—H15119.8
Sn1—C2—H2C109.5C15—C16—C17121.04 (17)
H2A—C2—H2C109.5C15—C16—H16119.5
H2B—C2—H2C109.5C17—C16—H16119.5
O1—C3—C8123.74 (16)C18—C17—C16119.80 (17)
O1—C3—C4118.25 (16)C18—C17—H17120.1
C8—C3—C4118.00 (16)C16—C17—H17120.1
C5—C4—C3121.42 (17)C17—C18—C19120.79 (17)
C5—C4—H4119.3C17—C18—H18119.6
C3—C4—H4119.3C19—C18—H18119.6
C4—C5—C6119.82 (17)C20—C19—C14119.00 (16)
C4—C5—H5120.1C20—C19—C18121.86 (17)
C6—C5—H5120.1C14—C19—C18119.14 (16)
C7—C6—C5120.72 (17)C11—C20—C19121.72 (17)
C7—C6—Cl1120.41 (15)C11—C20—H20119.1
C5—C6—Cl1118.83 (14)C19—C20—H20119.1
C6—C7—C8120.09 (17)
C1—Sn1—O1—C3−134.26 (17)Sn1—N1—C9—C80.8 (3)
C2—Sn1—O1—C397.15 (17)C3—C8—C9—N1−3.8 (3)
O2—Sn1—O1—C3−21.8 (2)C7—C8—C9—N1176.64 (17)
N1—Sn1—O1—C3−12.18 (16)Sn1—O2—C10—N2−1.3 (2)
O1—Sn1—O2—C1011.1 (2)Sn1—O2—C10—C11178.74 (12)
C1—Sn1—O2—C10123.65 (14)N1—N2—C10—O20.4 (2)
C2—Sn1—O2—C10−108.21 (14)N1—N2—C10—C11−179.60 (14)
N1—Sn1—O2—C101.11 (12)O2—C10—C11—C20−3.6 (2)
O1—Sn1—N1—C95.00 (15)N2—C10—C11—C20176.39 (16)
C1—Sn1—N1—C996.39 (16)O2—C10—C11—C12176.49 (17)
C2—Sn1—N1—C9−89.90 (16)N2—C10—C11—C12−3.5 (3)
O2—Sn1—N1—C9−179.19 (17)C20—C11—C12—O3−178.33 (17)
O1—Sn1—N1—N2−176.74 (12)C10—C11—C12—O31.6 (3)
C1—Sn1—N1—N2−85.36 (13)C20—C11—C12—C132.7 (3)
C2—Sn1—N1—N288.36 (12)C10—C11—C12—C13−177.41 (16)
O2—Sn1—N1—N2−0.93 (11)O3—C12—C13—C14179.31 (16)
C9—N1—N2—C10179.15 (15)C11—C12—C13—C14−1.7 (3)
Sn1—N1—N2—C100.64 (18)C12—C13—C14—C19−0.8 (3)
Sn1—O1—C3—C813.4 (3)C12—C13—C14—C15−179.92 (17)
Sn1—O1—C3—C4−166.82 (13)C19—C14—C15—C16−0.9 (3)
O1—C3—C4—C5−179.32 (17)C13—C14—C15—C16178.26 (17)
C8—C3—C4—C50.5 (3)C14—C15—C16—C170.7 (3)
C3—C4—C5—C62.8 (3)C15—C16—C17—C18−0.5 (3)
C4—C5—C6—C7−3.3 (3)C16—C17—C18—C190.5 (3)
C4—C5—C6—Cl1174.59 (14)C15—C14—C19—C20−178.65 (16)
C5—C6—C7—C80.5 (3)C13—C14—C19—C202.2 (2)
Cl1—C6—C7—C8−177.37 (14)C15—C14—C19—C180.9 (2)
O1—C3—C8—C7176.52 (17)C13—C14—C19—C18−178.24 (16)
C4—C3—C8—C7−3.3 (3)C17—C18—C19—C20178.81 (17)
O1—C3—C8—C9−3.0 (3)C17—C18—C19—C14−0.8 (3)
C4—C3—C8—C9177.20 (16)C12—C11—C20—C19−1.3 (3)
C6—C7—C8—C32.9 (3)C10—C11—C20—C19178.82 (15)
C6—C7—C8—C9−177.61 (16)C14—C19—C20—C11−1.1 (3)
N2—N1—C9—C8−177.52 (16)C18—C19—C20—C11179.27 (17)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N20.83 (1)1.86 (2)2.604 (2)148 (2)
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···N20.83 (1)1.86 (2)2.604 (2)148 (2)
Acknowledgements top

We thank the University of Malaya (PS320/2008C, RG020/09AFR) for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Labib, L., Khalil, T. E., Iskander, M. F. & Refaat, L. S. (1996). Polyhedron, 21, 3697–3707.

Samanta, B., Chakraborty, J., Dey, D. K. & Mitra, S. (2007). Struct. Chem. 18, 287–297.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.