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Acta Cryst. (2009). E65, m721    [ doi:10.1107/S1600536809020339 ]

(2-Amido-3-oxidopyridinium-[kappa]2N,O)dibenzylchloridotin(IV)

C. L. Tan, K. M. Lo and S. W. Ng

Abstract top

The Sn atom in the title compound, [Sn(C7H7)2(C5H5N2O)Cl], shows a distorted C2ClNOSn trigonal-bipyramidal coordination, with a Cl-Sn-O axial angle of 163.77 (3)°, but the C-Sn-C angle [141.43 (7)°] deviates from 120°. The chelating ligand exists in a zwitterionic form. Adjacent molecules are linked by an N-Hpyridinium...O hydrogen bond, forming a chain running along the c axis of the orthorhombic unit cell.

Related literature top

2-Amino-3-hydroxypyridine behaves as a mono-anion chelating to a metal atom; see: Gerber et al. (2004). The ligand also chelates in the neutral form; see: Palkina et al. (2000). The ligand exists as an isolated mono-cation in other metal salts; see: Halvorson et al. (1990); Place et al. (1998).

Experimental top

Dibenzyltin dichloride (0.37 g, 1 mmol) and 2-amino-3-hydroxypyridine (0.11 g, 1 mmol) were dissolved in chloroform (100 ml); the solution was heated for 1 hour. Slow evaporation of the filtrate afforded pale-yellow crystals.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2Ueq(C). The nitrogen-bound H atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.88±0.01 Å and individual isotropic temperature factors.

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 SnCl(C7H7)(C5H5N2O) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
(2-Amido-3-oxidopyridinium-κ2N,O)dibenzylchloridotin(IV) top
Crystal data top
[Sn(C7H7)2(C5H5N2O)Cl]F(000) = 1776
Mr = 445.50Dx = 1.663 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 9941 reflections
a = 11.0457 (1) Åθ = 2.4–28.2°
b = 16.8447 (2) ŵ = 1.59 mm−1
c = 19.1227 (2) ÅT = 133 K
V = 3558.00 (6) Å3Prism, pale-yellow
Z = 80.20 × 0.05 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		4086 independent reflections
Radiation source: fine-focus sealed tube3434 reflections with I > 2σ(I)
graphiteRint = 0.025
ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.640, Tmax = 0.746k = −21→21
32398 measured reflectionsl = −24→24
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)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0279P)2 + 2.1692P]
where P = (Fo2 + 2Fc2)/3
4086 reflections(Δ/σ)max = 0.004
225 parametersΔρmax = 0.58 e Å−3
2 restraintsΔρmin = −0.38 e Å−3
Crystal data top
[Sn(C7H7)2(C5H5N2O)Cl]V = 3558.00 (6) Å3
Mr = 445.50Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.0457 (1) ŵ = 1.59 mm−1
b = 16.8447 (2) ÅT = 133 K
c = 19.1227 (2) Å0.20 × 0.05 × 0.05 mm
Data collection top
Bruker SMART APEX
diffractometer		4086 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3434 reflections with I > 2σ(I)
Tmin = 0.640, Tmax = 0.746Rint = 0.025
32398 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.054Δρmax = 0.58 e Å−3
S = 1.01Δρmin = −0.38 e Å−3
4086 reflectionsAbsolute structure: ?
225 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sn10.497920 (10)0.547145 (7)0.324875 (6)0.01725 (5)
Cl10.65272 (4)0.45738 (3)0.37607 (3)0.02492 (10)
O10.40585 (10)0.64531 (8)0.26870 (6)0.0207 (3)
N10.68659 (13)0.70633 (9)0.19394 (8)0.0185 (3)
H10.7626 (10)0.6937 (12)0.2015 (11)0.024 (5)*
N20.63839 (13)0.61218 (9)0.28027 (8)0.0183 (3)
H20.7151 (10)0.6008 (13)0.2832 (12)0.033 (6)*
C10.43387 (17)0.46293 (11)0.24812 (10)0.0224 (4)
H1A0.44480.40790.26530.027*
H1B0.34690.47160.23830.027*
C20.50788 (15)0.47652 (12)0.18346 (10)0.0212 (4)
C30.46973 (18)0.53013 (12)0.13232 (10)0.0230 (4)
H30.39310.55520.13690.028*
C40.54191 (19)0.54737 (12)0.07487 (11)0.0261 (4)
H40.51470.58440.04080.031*
C50.65348 (18)0.51080 (12)0.06696 (10)0.0277 (4)
H50.70320.52280.02780.033*
C60.69168 (18)0.45658 (12)0.11679 (11)0.0274 (4)
H60.76760.43080.11140.033*
C70.62000 (17)0.43961 (12)0.17456 (10)0.0238 (4)
H70.64760.40250.20840.029*
C80.44732 (17)0.60092 (12)0.42300 (10)0.0229 (4)
H8A0.36550.62460.41980.027*
H8B0.44740.56090.46090.027*
C90.54035 (17)0.66398 (11)0.43697 (9)0.0216 (4)
C100.65205 (17)0.64382 (11)0.46612 (9)0.0234 (4)
H100.66650.59070.48050.028*
C110.74193 (18)0.70028 (12)0.47429 (10)0.0271 (4)
H110.81770.68540.49380.033*
C120.72242 (19)0.77828 (12)0.45420 (11)0.0286 (4)
H120.78410.81700.46020.034*
C130.6121 (2)0.79920 (12)0.42533 (11)0.0301 (4)
H130.59780.85260.41160.036*
C140.52218 (18)0.74232 (12)0.41639 (11)0.0265 (4)
H140.44720.75720.39590.032*
C150.48011 (15)0.68662 (11)0.22755 (10)0.0179 (4)
C160.44615 (17)0.74253 (11)0.17952 (10)0.0225 (4)
H160.36320.75650.17480.027*
C170.53422 (18)0.77968 (12)0.13674 (10)0.0246 (4)
H170.51030.81750.10260.030*
C180.65246 (17)0.76107 (11)0.14473 (10)0.0232 (4)
H180.71190.78590.11620.028*
C190.60653 (15)0.66784 (10)0.23445 (9)0.0158 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.01411 (7)0.02073 (8)0.01692 (8)−0.00099 (5)−0.00013 (4)0.00119 (4)
Cl10.0225 (2)0.0226 (2)0.0297 (2)0.00080 (18)−0.00556 (19)0.00552 (18)
O10.0125 (6)0.0273 (7)0.0223 (7)0.0028 (5)0.0014 (5)0.0027 (5)
N10.0132 (7)0.0216 (8)0.0209 (8)0.0025 (6)0.0013 (6)0.0014 (6)
N20.0111 (6)0.0226 (8)0.0212 (8)0.0013 (6)−0.0007 (6)0.0016 (6)
C10.0192 (9)0.0256 (9)0.0224 (9)−0.0051 (7)−0.0019 (7)−0.0006 (7)
C20.0197 (9)0.0216 (9)0.0223 (10)−0.0034 (7)−0.0026 (7)−0.0057 (7)
C30.0206 (8)0.0270 (10)0.0215 (10)0.0010 (8)−0.0028 (8)−0.0045 (7)
C40.0281 (10)0.0289 (10)0.0211 (10)−0.0017 (8)−0.0031 (8)−0.0012 (8)
C50.0261 (9)0.0334 (11)0.0237 (10)−0.0050 (9)0.0040 (8)−0.0080 (8)
C60.0210 (9)0.0320 (11)0.0292 (11)0.0026 (8)−0.0008 (8)−0.0098 (8)
C70.0235 (9)0.0232 (9)0.0247 (10)0.0001 (8)−0.0039 (7)−0.0043 (7)
C80.0196 (9)0.0300 (10)0.0191 (9)−0.0004 (8)0.0027 (7)0.0010 (8)
C90.0224 (9)0.0274 (10)0.0150 (9)0.0004 (8)0.0039 (7)−0.0015 (7)
C100.0290 (10)0.0244 (9)0.0168 (9)0.0025 (8)−0.0019 (7)−0.0013 (7)
C110.0231 (9)0.0374 (12)0.0208 (10)0.0008 (8)−0.0020 (8)−0.0052 (8)
C120.0324 (10)0.0301 (11)0.0235 (10)−0.0094 (9)0.0042 (8)−0.0053 (8)
C130.0405 (12)0.0246 (10)0.0253 (10)0.0011 (9)0.0036 (9)−0.0002 (8)
C140.0267 (10)0.0296 (11)0.0233 (10)0.0061 (8)0.0003 (8)−0.0016 (8)
C150.0131 (8)0.0219 (9)0.0186 (9)0.0011 (7)0.0000 (7)−0.0031 (7)
C160.0180 (9)0.0261 (10)0.0234 (10)0.0062 (8)−0.0020 (7)0.0011 (7)
C170.0248 (9)0.0265 (10)0.0226 (10)0.0055 (8)−0.0006 (8)0.0059 (8)
C180.0241 (9)0.0233 (9)0.0223 (10)0.0014 (8)0.0031 (8)0.0050 (7)
C190.0139 (7)0.0185 (8)0.0151 (9)0.0014 (6)−0.0007 (6)−0.0034 (6)
Geometric parameters (Å, °) top
Sn1—N22.0821 (15)C6—H60.9500
Sn1—C82.1573 (19)C7—H70.9500
Sn1—C12.1604 (18)C8—C91.502 (3)
Sn1—O12.2187 (12)C8—H8A0.9900
Sn1—Cl12.4836 (4)C8—H8B0.9900
O1—C151.333 (2)C9—C141.392 (3)
N1—C191.343 (2)C9—C101.396 (3)
N1—C181.370 (2)C10—C111.384 (3)
N1—H10.878 (9)C10—H100.9500
N2—C191.331 (2)C11—C121.386 (3)
N2—H20.871 (9)C11—H110.9500
C1—C21.500 (3)C12—C131.383 (3)
C1—H1A0.9900C12—H120.9500
C1—H1B0.9900C13—C141.391 (3)
C2—C71.396 (3)C13—H130.9500
C2—C31.396 (3)C14—H140.9500
C3—C41.388 (3)C15—C161.368 (3)
C3—H30.9500C15—C191.438 (2)
C4—C51.386 (3)C16—C171.417 (3)
C4—H40.9500C16—H160.9500
C5—C61.386 (3)C17—C181.352 (3)
C5—H50.9500C17—H170.9500
C6—C71.389 (3)C18—H180.9500
N2—Sn1—C8109.18 (7)C2—C7—H7119.6
N2—Sn1—C1108.13 (7)C9—C8—Sn1105.93 (12)
C8—Sn1—C1141.43 (7)C9—C8—H8A110.6
N2—Sn1—O175.58 (5)Sn1—C8—H8A110.6
C8—Sn1—O189.40 (6)C9—C8—H8B110.6
C1—Sn1—O190.59 (6)Sn1—C8—H8B110.6
N2—Sn1—Cl188.21 (4)H8A—C8—H8B108.7
C8—Sn1—Cl195.23 (5)C14—C9—C10118.10 (18)
C1—Sn1—Cl195.36 (5)C14—C9—C8121.45 (17)
O1—Sn1—Cl1163.77 (3)C10—C9—C8120.25 (17)
C15—O1—Sn1113.14 (10)C11—C10—C9120.81 (18)
C19—N1—C18122.68 (15)C11—C10—H10119.6
C19—N1—H1114.7 (14)C9—C10—H10119.6
C18—N1—H1122.6 (14)C10—C11—C12120.59 (19)
C19—N2—Sn1116.32 (11)C10—C11—H11119.7
C19—N2—H2117.0 (15)C12—C11—H11119.7
Sn1—N2—H2125.7 (15)C13—C12—C11119.29 (19)
C2—C1—Sn1106.34 (12)C13—C12—H12120.4
C2—C1—H1A110.5C11—C12—H12120.4
Sn1—C1—H1A110.5C12—C13—C14120.17 (19)
C2—C1—H1B110.5C12—C13—H13119.9
Sn1—C1—H1B110.5C14—C13—H13119.9
H1A—C1—H1B108.7C13—C14—C9121.04 (19)
C7—C2—C3118.06 (18)C13—C14—H14119.5
C7—C2—C1121.07 (18)C9—C14—H14119.5
C3—C2—C1120.77 (17)O1—C15—C16125.95 (16)
C4—C3—C2121.08 (18)O1—C15—C19115.38 (15)
C4—C3—H3119.5C16—C15—C19118.65 (16)
C2—C3—H3119.5C15—C16—C17120.23 (17)
C5—C4—C3120.27 (19)C15—C16—H16119.9
C5—C4—H4119.9C17—C16—H16119.9
C3—C4—H4119.9C18—C17—C16119.72 (18)
C6—C5—C4119.25 (19)C18—C17—H17120.1
C6—C5—H5120.4C16—C17—H17120.1
C4—C5—H5120.4C17—C18—N1119.96 (17)
C5—C6—C7120.60 (18)C17—C18—H18120.0
C5—C6—H6119.7N1—C18—H18120.0
C7—C6—H6119.7N2—C19—N1123.10 (15)
C6—C7—C2120.73 (19)N2—C19—C15118.18 (15)
C6—C7—H7119.6N1—C19—C15118.71 (16)
N2—Sn1—O1—C159.88 (12)Sn1—C8—C9—C1493.23 (18)
C8—Sn1—O1—C15119.87 (12)Sn1—C8—C9—C10−81.55 (18)
C1—Sn1—O1—C15−98.71 (12)C14—C9—C10—C110.1 (3)
Cl1—Sn1—O1—C1513.0 (2)C8—C9—C10—C11175.01 (17)
C8—Sn1—N2—C19−94.25 (14)C9—C10—C11—C120.6 (3)
C1—Sn1—N2—C1975.77 (14)C10—C11—C12—C13−0.4 (3)
O1—Sn1—N2—C19−10.04 (12)C11—C12—C13—C14−0.3 (3)
Cl1—Sn1—N2—C19170.83 (13)C12—C13—C14—C90.9 (3)
N2—Sn1—C1—C2−1.11 (14)C10—C9—C14—C13−0.8 (3)
C8—Sn1—C1—C2163.69 (12)C8—C9—C14—C13−175.65 (18)
O1—Sn1—C1—C273.91 (13)Sn1—O1—C15—C16170.06 (16)
Cl1—Sn1—C1—C2−90.98 (12)Sn1—O1—C15—C19−8.36 (19)
Sn1—C1—C2—C785.78 (19)O1—C15—C16—C17−177.14 (17)
Sn1—C1—C2—C3−90.42 (18)C19—C15—C16—C171.2 (3)
C7—C2—C3—C4−1.1 (3)C15—C16—C17—C18−1.6 (3)
C1—C2—C3—C4175.23 (18)C16—C17—C18—N10.2 (3)
C2—C3—C4—C50.6 (3)C19—N1—C18—C171.7 (3)
C3—C4—C5—C60.4 (3)Sn1—N2—C19—N1−169.87 (13)
C4—C5—C6—C7−0.8 (3)Sn1—N2—C19—C159.3 (2)
C5—C6—C7—C20.3 (3)C18—N1—C19—N2177.05 (17)
C3—C2—C7—C60.7 (3)C18—N1—C19—C15−2.1 (3)
C1—C2—C7—C6−175.64 (17)O1—C15—C19—N2−0.1 (2)
N2—Sn1—C8—C9−8.06 (14)C16—C15—C19—N2−178.61 (17)
C1—Sn1—C8—C9−172.75 (12)O1—C15—C19—N1179.10 (15)
O1—Sn1—C8—C9−82.56 (12)C16—C15—C19—N10.6 (3)
Cl1—Sn1—C8—C981.86 (12)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (1)1.87 (1)2.726 (2)165 (2)
Symmetry codes: (i) x+1/2, y, −z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (1)1.87 (1)2.726 (2)165 (2)
Symmetry codes: (i) x+1/2, y, −z+1/2.
Acknowledgements top

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

references
References top

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