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(2-Amido-3-oxidopyridinium-κ2N,O)di­benzyl­chloridotin(IV)

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 27 May 2009; accepted 28 May 2009; online 6 June 2009)

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

2-Amino-3-hydroxy­pyridine behaves as a mono-anion chelating to a metal atom; see: Gerber et al. (2004[Gerber, T. I. A., Luzipo, D. & Mayer, P. (2004). J. Coord. Chem. 57, 1419-1423.]). The ligand also chelates in the neutral form; see: Palkina et al. (2000[Palkina, K. K., Kuz'mina, N. E., Strashnova, S. V., Zaitsev, B. E., Koval'chukova, O. V., Nikitin, S. V., Goncharov, O. V. & Shchelokov, R. N. (2000). Russ. J. Inorg. Chem. 45, 515-520.]). The ligand exists as an isolated mono-cation in other metal salts; see: Halvorson et al. (1990[Halvorson, K. E., Patterson, C. & Willett, R. D. (1990). Acta Cryst. B46, 508-519.]); Place et al. (1998[Place, H., Scott, B., Long, G. S. & Willett, R. D. (1998). Inorg. Chim. Acta, 279, 1-6.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C7H7)2(C5H5N2O)Cl]

  • Mr = 445.50

  • Orthorhombic, P b c a

  • a = 11.0457 (1) Å

  • b = 16.8447 (2) Å

  • c = 19.1227 (2) Å

  • V = 3558.00 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 1.59 mm−1

  • T = 133 K

  • 0.20 × 0.05 × 0.05 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.640, Tmax = 0.746 (expected range = 0.792–0.923)

  • 32398 measured reflections

  • 4086 independent reflections

  • 3434 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.021

  • wR(F2) = 0.054

  • S = 1.01

  • 4086 reflections

  • 225 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.58 e Å−3

  • Δρmin = −0.38 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.88 (1) 1.87 (1) 2.726 (2) 165 (2)
Symmetry code: (i) [x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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 m3
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 mm1
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)
Graphite monochromatorRint = 0.025
ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.640, Tmax = 0.746k = 2121
32398 measured reflectionsl = 2424
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 Å3
2 restraintsΔρmin = 0.38 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0212 restraints
wR(F2) = 0.054H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.58 e Å3
4086 reflectionsΔρmin = 0.38 e Å3
225 parameters
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, º) 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—C1081.55 (18)
C1—Sn1—O1—C1598.71 (12)C14—C9—C10—C110.1 (3)
Cl1—Sn1—O1—C1513.0 (2)C8—C9—C10—C11175.01 (17)
C8—Sn1—N2—C1994.25 (14)C9—C10—C11—C120.6 (3)
C1—Sn1—N2—C1975.77 (14)C10—C11—C12—C130.4 (3)
O1—Sn1—N2—C1910.04 (12)C11—C12—C13—C140.3 (3)
Cl1—Sn1—N2—C19170.83 (13)C12—C13—C14—C90.9 (3)
N2—Sn1—C1—C21.11 (14)C10—C9—C14—C130.8 (3)
C8—Sn1—C1—C2163.69 (12)C8—C9—C14—C13175.65 (18)
O1—Sn1—C1—C273.91 (13)Sn1—O1—C15—C16170.06 (16)
Cl1—Sn1—C1—C290.98 (12)Sn1—O1—C15—C198.36 (19)
Sn1—C1—C2—C785.78 (19)O1—C15—C16—C17177.14 (17)
Sn1—C1—C2—C390.42 (18)C19—C15—C16—C171.2 (3)
C7—C2—C3—C41.1 (3)C15—C16—C17—C181.6 (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—N1169.87 (13)
C4—C5—C6—C70.8 (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—C152.1 (3)
C1—C2—C7—C6175.64 (17)O1—C15—C19—N20.1 (2)
N2—Sn1—C8—C98.06 (14)C16—C15—C19—N2178.61 (17)
C1—Sn1—C8—C9172.75 (12)O1—C15—C19—N1179.10 (15)
O1—Sn1—C8—C982.56 (12)C16—C15—C19—N10.6 (3)
Cl1—Sn1—C8—C981.86 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (1)1.87 (1)2.726 (2)165 (2)
Symmetry code: (i) x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formula[Sn(C7H7)2(C5H5N2O)Cl]
Mr445.50
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)133
a, b, c (Å)11.0457 (1), 16.8447 (2), 19.1227 (2)
V3)3558.00 (6)
Z8
Radiation typeMo Kα
µ (mm1)1.59
Crystal size (mm)0.20 × 0.05 × 0.05
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.640, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
32398, 4086, 3434
Rint0.025
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.021, 0.054, 1.01
No. of reflections4086
No. of parameters225
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.58, 0.38

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (1)1.87 (1)2.726 (2)165 (2)
Symmetry code: (i) x+1/2, y, z+1/2.
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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