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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m161.
Published online 2010 January 16. doi:  10.1107/S1600536810001133
PMCID: PMC2979755

[N′-(5-Bromo-2-oxidobenzyl­idene-κO)-3-hydr­oxy-2-naphthohydrazidato-κ2 N′,O]dimethyl­tin(IV)

Abstract

The SnIV atom in the title compound, [Sn(CH3)2(C18H11BrN2O3)], shows a distorted cis-C2NO2Sn trigonal-bipyramidal coordination geometry, with an axial O—Sn—O angle of 155.27 (9)°. The presence of an intra­molecular O—H(...)N hydrogen bond between the amido N atom and hydr­oxy H atom in the Schiff base ligand helps to stabilize the overall mol­ecular structure.

Related literature

For related structures, see Lee et al. (2009a [triangle],b [triangle]). For similar hydrazone dianions acting as O,N,O′-chelate ligands to tin in organotin compounds, see: Labib et al. (1996 [triangle]); Samanta et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m161-scheme1.jpg

Experimental

Crystal data

  • [Sn(CH3)2(C18H11BrN2O3)]
  • M r = 531.96
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m161-efi1.jpg
  • a = 6.8662 (5) Å
  • b = 11.7998 (9) Å
  • c = 11.9365 (9) Å
  • α = 87.464 (1)°
  • β = 76.128 (1)°
  • γ = 81.213 (1)°
  • V = 927.84 (12) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 3.55 mm−1
  • T = 145 K
  • 0.39 × 0.37 × 0.09 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.338, T max = 0.740
  • 5350 measured reflections
  • 4028 independent reflections
  • 3703 reflections with I > 2σ(I)
  • R int = 0.016

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.079
  • S = 1.14
  • 4028 reflections
  • 245 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.63 e Å−3
  • Δρmin = −0.76 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]0); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810001133/sj2691sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001133/sj2691Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

The Schiff base ligand was prepared by the condensation reaction of 3-hydroxy-2-naphthoyl hydrazide with 5-bromosalicylaldehyde. The title compound was prepared by refluxing the Schiff base (0.74 g, 2.0 mmol) with dimethyltin oxide (0.32 g, 2.0 mmol) in toluene for 6 h. The solution was filtered and left for recrystallization for a week during which yellow crystals were obtained.

Refinement

All H-atoms were positioned geometrically and refined using a riding model with d(C-H) = 0.95Å, Uiso=1.2Ueq (C) for aromatic 0.98Å, Uiso = 1.5Ueq (C) for CH3 atoms and 0.84Å, Uiso = 1.5Ueq (O) for the OH group.

Figures

Fig. 1.
The molecular structure of [N'-(5-bromo-2-oxidobenzylidene-κO)-3-hydroxy-2- naphthohydrazidato-κ2N',O]dimethyltin(IV) showing 70% probability displacement ellipsoids and the atom numbering. Hydrogen atoms are drawn as spheres of arbitrary ...

Crystal data

[Sn(CH3)2(C18H11BrN2O3)]Z = 2
Mr = 531.96F(000) = 520
Triclinic, P1Dx = 1.904 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.8662 (5) ÅCell parameters from 3900 reflections
b = 11.7998 (9) Åθ = 2.5–30.6°
c = 11.9365 (9) ŵ = 3.55 mm1
α = 87.464 (1)°T = 145 K
β = 76.128 (1)°Plate, yellow
γ = 81.213 (1)°0.39 × 0.37 × 0.09 mm
V = 927.84 (12) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer4028 independent reflections
Radiation source: fine-focus sealed tube3703 reflections with I > 2σ(I)
graphiteRint = 0.016
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.338, Tmax = 0.740k = −10→15
5350 measured reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.14w = 1/[σ2(Fo2) + (0.0316P)2 + 1.8608P] where P = (Fo2 + 2Fc2)/3
4028 reflections(Δ/σ)max = 0.001
245 parametersΔρmax = 0.63 e Å3
1 restraintΔρmin = −0.75 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Sn10.75049 (3)0.561594 (19)0.670242 (18)0.01412 (8)
Br10.57215 (5)−0.06224 (3)0.64595 (3)0.02011 (9)
N10.5307 (4)0.4692 (2)0.7889 (2)0.0141 (5)
N20.3995 (4)0.5332 (3)0.8788 (2)0.0172 (6)
O10.8546 (4)0.4001 (2)0.5966 (2)0.0202 (5)
O20.5723 (4)0.6809 (2)0.7987 (2)0.0228 (5)
O30.1095 (4)0.5698 (2)1.0656 (2)0.0219 (5)
H30.17500.53441.00540.033*
C10.6138 (5)0.2791 (3)0.6996 (3)0.0141 (6)
C20.7792 (5)0.3027 (3)0.6092 (3)0.0152 (6)
C30.8681 (5)0.2152 (3)0.5277 (3)0.0188 (7)
H3A0.97760.22880.46550.023*
C40.7999 (5)0.1105 (3)0.5364 (3)0.0158 (6)
H40.85930.05410.47900.019*
C50.6435 (5)0.0871 (3)0.6295 (3)0.0164 (6)
C60.5524 (5)0.1702 (3)0.7093 (3)0.0154 (6)
H60.44590.15400.77230.019*
C70.5032 (5)0.3630 (3)0.7853 (3)0.0150 (6)
H70.39990.33790.84500.018*
C80.4332 (5)0.6410 (3)0.8761 (3)0.0164 (6)
C90.3027 (5)0.7184 (3)0.9668 (3)0.0151 (6)
C100.1483 (5)0.6797 (3)1.0581 (3)0.0147 (6)
C110.0383 (5)0.7555 (3)1.1419 (3)0.0154 (6)
H11−0.06020.72911.20370.018*
C120.0673 (5)0.8711 (3)1.1392 (3)0.0139 (6)
C13−0.0460 (5)0.9515 (3)1.2244 (3)0.0189 (7)
H13−0.14290.92671.28800.023*
C14−0.0175 (5)1.0647 (3)1.2160 (3)0.0190 (7)
H14−0.09621.11741.27320.023*
C150.1279 (5)1.1033 (3)1.1232 (3)0.0192 (7)
H150.14691.18161.11860.023*
C160.2407 (5)1.0289 (3)1.0405 (3)0.0164 (6)
H160.33761.05580.97820.020*
C170.2153 (5)0.9112 (3)1.0461 (3)0.0138 (6)
C180.3312 (5)0.8320 (3)0.9627 (3)0.0152 (6)
H180.43220.85730.90170.018*
C191.0295 (5)0.5826 (3)0.7067 (3)0.0201 (7)
H19A1.04780.53670.77480.030*
H19B1.02910.66370.72160.030*
H19C1.14090.55720.64050.030*
C200.6241 (5)0.6376 (3)0.5344 (3)0.0227 (7)
H20A0.49330.61170.53910.034*
H20B0.71650.61500.46010.034*
H20C0.60400.72130.54120.034*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.01425 (12)0.01281 (13)0.01497 (12)−0.00358 (8)−0.00180 (8)−0.00023 (8)
Br10.02169 (17)0.01283 (18)0.02579 (18)−0.00506 (13)−0.00342 (14)−0.00316 (13)
N10.0149 (12)0.0107 (13)0.0174 (13)−0.0042 (10)−0.0034 (10)0.0001 (10)
N20.0154 (13)0.0220 (15)0.0131 (12)−0.0028 (11)−0.0010 (10)−0.0018 (11)
O10.0197 (12)0.0140 (12)0.0244 (12)−0.0038 (9)0.0011 (10)−0.0017 (10)
O20.0216 (12)0.0197 (13)0.0232 (12)−0.0073 (10)0.0054 (10)−0.0029 (10)
O30.0292 (13)0.0127 (12)0.0214 (12)−0.0114 (10)0.0050 (10)−0.0056 (9)
C10.0160 (14)0.0122 (15)0.0151 (14)−0.0024 (12)−0.0058 (12)−0.0001 (12)
C20.0162 (15)0.0134 (16)0.0172 (15)−0.0026 (12)−0.0061 (12)0.0000 (12)
C30.0164 (15)0.0223 (18)0.0160 (15)−0.0008 (13)−0.0022 (12)0.0031 (13)
C40.0175 (15)0.0133 (16)0.0168 (15)−0.0006 (12)−0.0051 (12)−0.0014 (12)
C50.0173 (15)0.0141 (16)0.0194 (16)−0.0024 (12)−0.0075 (12)−0.0002 (13)
C60.0146 (14)0.0159 (16)0.0171 (15)−0.0062 (12)−0.0042 (12)0.0015 (12)
C70.0157 (14)0.0140 (16)0.0168 (15)−0.0063 (12)−0.0049 (12)0.0033 (12)
C80.0131 (14)0.0223 (18)0.0143 (15)−0.0037 (12)−0.0040 (12)0.0021 (13)
C90.0151 (14)0.0150 (16)0.0157 (15)−0.0012 (12)−0.0051 (12)−0.0013 (12)
C100.0181 (15)0.0119 (15)0.0155 (15)−0.0045 (12)−0.0047 (12)−0.0025 (12)
C110.0154 (14)0.0174 (17)0.0139 (14)−0.0057 (12)−0.0024 (12)−0.0015 (12)
C120.0139 (14)0.0144 (16)0.0149 (14)−0.0036 (12)−0.0050 (11)−0.0022 (12)
C130.0145 (15)0.0284 (19)0.0137 (15)−0.0037 (13)−0.0029 (12)0.0001 (13)
C140.0202 (16)0.0201 (18)0.0178 (16)−0.0024 (13)−0.0059 (13)−0.0044 (13)
C150.0207 (16)0.0173 (17)0.0206 (16)−0.0011 (13)−0.0073 (13)−0.0035 (13)
C160.0182 (15)0.0120 (16)0.0202 (16)−0.0047 (12)−0.0051 (12)−0.0025 (12)
C170.0162 (14)0.0134 (15)0.0125 (14)−0.0016 (12)−0.0049 (11)−0.0024 (12)
C180.0147 (14)0.0176 (17)0.0132 (14)−0.0020 (12)−0.0035 (11)−0.0007 (12)
C190.0173 (15)0.0249 (19)0.0193 (16)−0.0090 (14)−0.0031 (13)−0.0007 (14)
C200.0225 (17)0.0223 (19)0.0238 (17)−0.0015 (14)−0.0079 (14)0.0017 (14)

Geometric parameters (Å, °)

Sn1—O12.084 (2)C8—C91.477 (5)
Sn1—C192.116 (3)C9—C181.381 (5)
Sn1—C202.120 (3)C9—C101.438 (4)
Sn1—O22.143 (2)C10—C111.372 (5)
Sn1—N12.194 (3)C11—C121.406 (5)
Br1—C51.890 (3)C11—H110.9500
N1—C71.300 (4)C12—C131.421 (5)
N1—N21.390 (4)C12—C171.432 (4)
N2—C81.324 (5)C13—C141.375 (5)
O1—C21.320 (4)C13—H130.9500
O2—C81.290 (4)C14—C151.412 (5)
O3—C101.358 (4)C14—H140.9500
O3—H30.8400C15—C161.360 (5)
C1—C61.404 (4)C15—H150.9500
C1—C21.419 (4)C16—C171.422 (5)
C1—C71.446 (5)C16—H160.9500
C2—C31.413 (5)C17—C181.405 (4)
C3—C41.377 (5)C18—H180.9500
C3—H3A0.9500C19—H19A0.9800
C4—C51.399 (5)C19—H19B0.9800
C4—H40.9500C19—H19C0.9800
C5—C61.367 (5)C20—H20A0.9800
C6—H60.9500C20—H20B0.9800
C7—H70.9500C20—H20C0.9800
O1—Sn1—C1995.10 (12)C18—C9—C8118.2 (3)
O1—Sn1—C2097.09 (13)C10—C9—C8122.5 (3)
C19—Sn1—C20127.84 (14)O3—C10—C11118.6 (3)
O1—Sn1—O2155.27 (9)O3—C10—C9122.3 (3)
C19—Sn1—O294.33 (12)C11—C10—C9119.2 (3)
C20—Sn1—O295.04 (13)C10—C11—C12121.9 (3)
O1—Sn1—N183.01 (10)C10—C11—H11119.0
C19—Sn1—N1121.63 (12)C12—C11—H11119.0
C20—Sn1—N1110.12 (12)C11—C12—C13123.0 (3)
O2—Sn1—N172.59 (10)C11—C12—C17119.2 (3)
C7—N1—N2115.3 (3)C13—C12—C17117.8 (3)
C7—N1—Sn1128.8 (2)C14—C13—C12121.0 (3)
N2—N1—Sn1115.9 (2)C14—C13—H13119.5
C8—N2—N1112.2 (3)C12—C13—H13119.5
C2—O1—Sn1133.1 (2)C13—C14—C15120.6 (3)
C8—O2—Sn1115.9 (2)C13—C14—H14119.7
C10—O3—H3109.5C15—C14—H14119.7
C6—C1—C2120.1 (3)C16—C15—C14120.3 (3)
C6—C1—C7117.1 (3)C16—C15—H15119.9
C2—C1—C7122.8 (3)C14—C15—H15119.9
O1—C2—C3118.3 (3)C15—C16—C17120.7 (3)
O1—C2—C1124.5 (3)C15—C16—H16119.6
C3—C2—C1117.2 (3)C17—C16—H16119.6
C4—C3—C2121.6 (3)C18—C17—C16122.1 (3)
C4—C3—H3A119.2C18—C17—C12118.3 (3)
C2—C3—H3A119.2C16—C17—C12119.6 (3)
C3—C4—C5120.2 (3)C9—C18—C17121.9 (3)
C3—C4—H4119.9C9—C18—H18119.0
C5—C4—H4119.9C17—C18—H18119.0
C6—C5—C4119.8 (3)Sn1—C19—H19A109.5
C6—C5—Br1121.4 (2)Sn1—C19—H19B109.5
C4—C5—Br1118.7 (3)H19A—C19—H19B109.5
C5—C6—C1120.9 (3)Sn1—C19—H19C109.5
C5—C6—H6119.5H19A—C19—H19C109.5
C1—C6—H6119.5H19B—C19—H19C109.5
N1—C7—C1126.6 (3)Sn1—C20—H20A109.5
N1—C7—H7116.7Sn1—C20—H20B109.5
C1—C7—H7116.7H20A—C20—H20B109.5
O2—C8—N2123.4 (3)Sn1—C20—H20C109.5
O2—C8—C9119.1 (3)H20A—C20—H20C109.5
N2—C8—C9117.5 (3)H20B—C20—H20C109.5
C18—C9—C10119.4 (3)
O1—Sn1—N1—C7−5.4 (3)Sn1—N1—C7—C1−0.2 (5)
C19—Sn1—N1—C7−97.1 (3)C6—C1—C7—N1−177.1 (3)
C20—Sn1—N1—C789.6 (3)C2—C1—C7—N13.5 (5)
O2—Sn1—N1—C7178.6 (3)Sn1—O2—C8—N20.3 (4)
O1—Sn1—N1—N2176.3 (2)Sn1—O2—C8—C9−179.4 (2)
C19—Sn1—N1—N284.6 (2)N1—N2—C8—O20.0 (4)
C20—Sn1—N1—N2−88.7 (2)N1—N2—C8—C9179.6 (3)
O2—Sn1—N1—N20.3 (2)O2—C8—C9—C182.0 (4)
C7—N1—N2—C8−178.8 (3)N2—C8—C9—C18−177.7 (3)
Sn1—N1—N2—C8−0.3 (3)O2—C8—C9—C10−178.2 (3)
C19—Sn1—O1—C2133.7 (3)N2—C8—C9—C102.2 (5)
C20—Sn1—O1—C2−97.1 (3)C18—C9—C10—O3178.5 (3)
O2—Sn1—O1—C221.7 (4)C8—C9—C10—O3−1.4 (5)
N1—Sn1—O1—C212.4 (3)C18—C9—C10—C11−2.7 (5)
O1—Sn1—O2—C8−10.0 (4)C8—C9—C10—C11177.4 (3)
C19—Sn1—O2—C8−122.1 (2)O3—C10—C11—C12−178.9 (3)
C20—Sn1—O2—C8109.2 (2)C9—C10—C11—C122.2 (5)
N1—Sn1—O2—C8−0.3 (2)C10—C11—C12—C13179.4 (3)
Sn1—O1—C2—C3166.5 (2)C10—C11—C12—C170.2 (5)
Sn1—O1—C2—C1−13.5 (5)C11—C12—C13—C14−177.7 (3)
C6—C1—C2—O1−176.3 (3)C17—C12—C13—C141.5 (5)
C7—C1—C2—O13.1 (5)C12—C13—C14—C15−1.0 (5)
C6—C1—C2—C33.7 (4)C13—C14—C15—C160.4 (5)
C7—C1—C2—C3−177.0 (3)C14—C15—C16—C17−0.3 (5)
O1—C2—C3—C4178.9 (3)C15—C16—C17—C18−179.2 (3)
C1—C2—C3—C4−1.1 (5)C15—C16—C17—C120.9 (5)
C2—C3—C4—C5−2.2 (5)C11—C12—C17—C18−2.1 (4)
C3—C4—C5—C62.8 (5)C13—C12—C17—C18178.7 (3)
C3—C4—C5—Br1−174.0 (2)C11—C12—C17—C16177.8 (3)
C4—C5—C6—C1−0.2 (5)C13—C12—C17—C16−1.4 (4)
Br1—C5—C6—C1176.6 (2)C10—C9—C18—C170.8 (5)
C2—C1—C6—C5−3.1 (5)C8—C9—C18—C17−179.3 (3)
C7—C1—C6—C5177.5 (3)C16—C17—C18—C9−178.3 (3)
N2—N1—C7—C1178.1 (3)C12—C17—C18—C91.6 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N20.841.882.611 (4)144

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2691).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). 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.
  • Lee, S. M., Lo, K. M., Mohd Ali, H. & Ng, S. W. (2009a). Acta Cryst. E65, m816. [PMC free article] [PubMed]
  • Lee, S. M., Lo, K. M., Ali, H. M. & Ng, S. W. (2009b). Acta Cryst. E65, m862. [PMC free article] [PubMed]
  • 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. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography