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

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

doi:10.1107/S1600536809020339

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m721

doi:10.1107/S1600536809020339

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

Chui Lian Tan,^a Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^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—H_pyridinium⋯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 ). 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

Crystal data

[Sn(C₇H₇)₂(C₅H₅N₂O)Cl]
M_r = 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 ) T_min = 0.640, T_max = 0.746 (expected range = 0.792–0.923)
32398 measured reflections
4086 independent reflections
3434 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020339/tk2469sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020339/tk2469Isup2.hkl

checkCIF report

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.

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

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
M_r = 445.50	D_x = 1.663 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9941 reflections
a = 11.0457 (1) Å	θ = 2.4–28.2°
b = 16.8447 (2) Å	µ = 1.59 mm⁻¹
c = 19.1227 (2) Å	T = 133 K
V = 3558.00 (6) Å³	Prism, pale-yellow
Z = 8	0.20 × 0.05 × 0.05 mm

Data collection top

Bruker SMART APEX diffractometer	4086 independent reflections
Radiation source: fine-focus sealed tube	3434 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.640, T_max = 0.746	k = −21→21
32398 measured reflections	l = −24→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0279P)² + 2.1692P] where P = (F_o² + 2F_c²)/3
4086 reflections	(Δ/σ)_max = 0.004
225 parameters	Δρ_max = 0.58 e Å⁻³
2 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

[Sn(C₇H₇)₂(C₅H₅N₂O)Cl]	V = 3558.00 (6) Å³
M_r = 445.50	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.0457 (1) Å	µ = 1.59 mm⁻¹
b = 16.8447 (2) Å	T = 133 K
c = 19.1227 (2) Å	0.20 × 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)
T_min = 0.640, T_max = 0.746	R_int = 0.025
32398 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	2 restraints
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.58 e Å⁻³
4086 reflections	Δρ_min = −0.38 e Å⁻³
225 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.497920 (10)	0.547145 (7)	0.324875 (6)	0.01725 (5)
Cl1	0.65272 (4)	0.45738 (3)	0.37607 (3)	0.02492 (10)
O1	0.40585 (10)	0.64531 (8)	0.26870 (6)	0.0207 (3)
N1	0.68659 (13)	0.70633 (9)	0.19394 (8)	0.0185 (3)
H1	0.7626 (10)	0.6937 (12)	0.2015 (11)	0.024 (5)*
N2	0.63839 (13)	0.61218 (9)	0.28027 (8)	0.0183 (3)
H2	0.7151 (10)	0.6008 (13)	0.2832 (12)	0.033 (6)*
C1	0.43387 (17)	0.46293 (11)	0.24812 (10)	0.0224 (4)
H1A	0.4448	0.4079	0.2653	0.027*
H1B	0.3469	0.4716	0.2383	0.027*
C2	0.50788 (15)	0.47652 (12)	0.18346 (10)	0.0212 (4)
C3	0.46973 (18)	0.53013 (12)	0.13232 (10)	0.0230 (4)
H3	0.3931	0.5552	0.1369	0.028*
C4	0.54191 (19)	0.54737 (12)	0.07487 (11)	0.0261 (4)
H4	0.5147	0.5844	0.0408	0.031*
C5	0.65348 (18)	0.51080 (12)	0.06696 (10)	0.0277 (4)
H5	0.7032	0.5228	0.0278	0.033*
C6	0.69168 (18)	0.45658 (12)	0.11679 (11)	0.0274 (4)
H6	0.7676	0.4308	0.1114	0.033*
C7	0.62000 (17)	0.43961 (12)	0.17456 (10)	0.0238 (4)
H7	0.6476	0.4025	0.2084	0.029*
C8	0.44732 (17)	0.60092 (12)	0.42300 (10)	0.0229 (4)
H8A	0.3655	0.6246	0.4198	0.027*
H8B	0.4474	0.5609	0.4609	0.027*
C9	0.54035 (17)	0.66398 (11)	0.43697 (9)	0.0216 (4)
C10	0.65205 (17)	0.64382 (11)	0.46612 (9)	0.0234 (4)
H10	0.6665	0.5907	0.4805	0.028*
C11	0.74193 (18)	0.70028 (12)	0.47429 (10)	0.0271 (4)
H11	0.8177	0.6854	0.4938	0.033*
C12	0.72242 (19)	0.77828 (12)	0.45420 (11)	0.0286 (4)
H12	0.7841	0.8170	0.4602	0.034*
C13	0.6121 (2)	0.79920 (12)	0.42533 (11)	0.0301 (4)
H13	0.5978	0.8526	0.4116	0.036*
C14	0.52218 (18)	0.74232 (12)	0.41639 (11)	0.0265 (4)
H14	0.4472	0.7572	0.3959	0.032*
C15	0.48011 (15)	0.68662 (11)	0.22755 (10)	0.0179 (4)
C16	0.44615 (17)	0.74253 (11)	0.17952 (10)	0.0225 (4)
H16	0.3632	0.7565	0.1748	0.027*
C17	0.53422 (18)	0.77968 (12)	0.13674 (10)	0.0246 (4)
H17	0.5103	0.8175	0.1026	0.030*
C18	0.65246 (17)	0.76107 (11)	0.14473 (10)	0.0232 (4)
H18	0.7119	0.7859	0.1162	0.028*
C19	0.60653 (15)	0.66784 (10)	0.23445 (9)	0.0158 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01411 (7)	0.02073 (8)	0.01692 (8)	−0.00099 (5)	−0.00013 (4)	0.00119 (4)
Cl1	0.0225 (2)	0.0226 (2)	0.0297 (2)	0.00080 (18)	−0.00556 (19)	0.00552 (18)
O1	0.0125 (6)	0.0273 (7)	0.0223 (7)	0.0028 (5)	0.0014 (5)	0.0027 (5)
N1	0.0132 (7)	0.0216 (8)	0.0209 (8)	0.0025 (6)	0.0013 (6)	0.0014 (6)
N2	0.0111 (6)	0.0226 (8)	0.0212 (8)	0.0013 (6)	−0.0007 (6)	0.0016 (6)
C1	0.0192 (9)	0.0256 (9)	0.0224 (9)	−0.0051 (7)	−0.0019 (7)	−0.0006 (7)
C2	0.0197 (9)	0.0216 (9)	0.0223 (10)	−0.0034 (7)	−0.0026 (7)	−0.0057 (7)
C3	0.0206 (8)	0.0270 (10)	0.0215 (10)	0.0010 (8)	−0.0028 (8)	−0.0045 (7)
C4	0.0281 (10)	0.0289 (10)	0.0211 (10)	−0.0017 (8)	−0.0031 (8)	−0.0012 (8)
C5	0.0261 (9)	0.0334 (11)	0.0237 (10)	−0.0050 (9)	0.0040 (8)	−0.0080 (8)
C6	0.0210 (9)	0.0320 (11)	0.0292 (11)	0.0026 (8)	−0.0008 (8)	−0.0098 (8)
C7	0.0235 (9)	0.0232 (9)	0.0247 (10)	0.0001 (8)	−0.0039 (7)	−0.0043 (7)
C8	0.0196 (9)	0.0300 (10)	0.0191 (9)	−0.0004 (8)	0.0027 (7)	0.0010 (8)
C9	0.0224 (9)	0.0274 (10)	0.0150 (9)	0.0004 (8)	0.0039 (7)	−0.0015 (7)
C10	0.0290 (10)	0.0244 (9)	0.0168 (9)	0.0025 (8)	−0.0019 (7)	−0.0013 (7)
C11	0.0231 (9)	0.0374 (12)	0.0208 (10)	0.0008 (8)	−0.0020 (8)	−0.0052 (8)
C12	0.0324 (10)	0.0301 (11)	0.0235 (10)	−0.0094 (9)	0.0042 (8)	−0.0053 (8)
C13	0.0405 (12)	0.0246 (10)	0.0253 (10)	0.0011 (9)	0.0036 (9)	−0.0002 (8)
C14	0.0267 (10)	0.0296 (11)	0.0233 (10)	0.0061 (8)	0.0003 (8)	−0.0016 (8)
C15	0.0131 (8)	0.0219 (9)	0.0186 (9)	0.0011 (7)	0.0000 (7)	−0.0031 (7)
C16	0.0180 (9)	0.0261 (10)	0.0234 (10)	0.0062 (8)	−0.0020 (7)	0.0011 (7)
C17	0.0248 (9)	0.0265 (10)	0.0226 (10)	0.0055 (8)	−0.0006 (8)	0.0059 (8)
C18	0.0241 (9)	0.0233 (9)	0.0223 (10)	0.0014 (8)	0.0031 (8)	0.0050 (7)
C19	0.0139 (7)	0.0185 (8)	0.0151 (9)	0.0014 (6)	−0.0007 (6)	−0.0034 (6)

Geometric parameters (Å, º) top

Sn1—N2	2.0821 (15)	C6—H6	0.9500
Sn1—C8	2.1573 (19)	C7—H7	0.9500
Sn1—C1	2.1604 (18)	C8—C9	1.502 (3)
Sn1—O1	2.2187 (12)	C8—H8A	0.9900
Sn1—Cl1	2.4836 (4)	C8—H8B	0.9900
O1—C15	1.333 (2)	C9—C14	1.392 (3)
N1—C19	1.343 (2)	C9—C10	1.396 (3)
N1—C18	1.370 (2)	C10—C11	1.384 (3)
N1—H1	0.878 (9)	C10—H10	0.9500
N2—C19	1.331 (2)	C11—C12	1.386 (3)
N2—H2	0.871 (9)	C11—H11	0.9500
C1—C2	1.500 (3)	C12—C13	1.383 (3)
C1—H1A	0.9900	C12—H12	0.9500
C1—H1B	0.9900	C13—C14	1.391 (3)
C2—C7	1.396 (3)	C13—H13	0.9500
C2—C3	1.396 (3)	C14—H14	0.9500
C3—C4	1.388 (3)	C15—C16	1.368 (3)
C3—H3	0.9500	C15—C19	1.438 (2)
C4—C5	1.386 (3)	C16—C17	1.417 (3)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.386 (3)	C17—C18	1.352 (3)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.389 (3)	C18—H18	0.9500

N2—Sn1—C8	109.18 (7)	C2—C7—H7	119.6
N2—Sn1—C1	108.13 (7)	C9—C8—Sn1	105.93 (12)
C8—Sn1—C1	141.43 (7)	C9—C8—H8A	110.6
N2—Sn1—O1	75.58 (5)	Sn1—C8—H8A	110.6
C8—Sn1—O1	89.40 (6)	C9—C8—H8B	110.6
C1—Sn1—O1	90.59 (6)	Sn1—C8—H8B	110.6
N2—Sn1—Cl1	88.21 (4)	H8A—C8—H8B	108.7
C8—Sn1—Cl1	95.23 (5)	C14—C9—C10	118.10 (18)
C1—Sn1—Cl1	95.36 (5)	C14—C9—C8	121.45 (17)
O1—Sn1—Cl1	163.77 (3)	C10—C9—C8	120.25 (17)
C15—O1—Sn1	113.14 (10)	C11—C10—C9	120.81 (18)
C19—N1—C18	122.68 (15)	C11—C10—H10	119.6
C19—N1—H1	114.7 (14)	C9—C10—H10	119.6
C18—N1—H1	122.6 (14)	C10—C11—C12	120.59 (19)
C19—N2—Sn1	116.32 (11)	C10—C11—H11	119.7
C19—N2—H2	117.0 (15)	C12—C11—H11	119.7
Sn1—N2—H2	125.7 (15)	C13—C12—C11	119.29 (19)
C2—C1—Sn1	106.34 (12)	C13—C12—H12	120.4
C2—C1—H1A	110.5	C11—C12—H12	120.4
Sn1—C1—H1A	110.5	C12—C13—C14	120.17 (19)
C2—C1—H1B	110.5	C12—C13—H13	119.9
Sn1—C1—H1B	110.5	C14—C13—H13	119.9
H1A—C1—H1B	108.7	C13—C14—C9	121.04 (19)
C7—C2—C3	118.06 (18)	C13—C14—H14	119.5
C7—C2—C1	121.07 (18)	C9—C14—H14	119.5
C3—C2—C1	120.77 (17)	O1—C15—C16	125.95 (16)
C4—C3—C2	121.08 (18)	O1—C15—C19	115.38 (15)
C4—C3—H3	119.5	C16—C15—C19	118.65 (16)
C2—C3—H3	119.5	C15—C16—C17	120.23 (17)
C5—C4—C3	120.27 (19)	C15—C16—H16	119.9
C5—C4—H4	119.9	C17—C16—H16	119.9
C3—C4—H4	119.9	C18—C17—C16	119.72 (18)
C6—C5—C4	119.25 (19)	C18—C17—H17	120.1
C6—C5—H5	120.4	C16—C17—H17	120.1
C4—C5—H5	120.4	C17—C18—N1	119.96 (17)
C5—C6—C7	120.60 (18)	C17—C18—H18	120.0
C5—C6—H6	119.7	N1—C18—H18	120.0
C7—C6—H6	119.7	N2—C19—N1	123.10 (15)
C6—C7—C2	120.73 (19)	N2—C19—C15	118.18 (15)
C6—C7—H7	119.6	N1—C19—C15	118.71 (16)

N2—Sn1—O1—C15	9.88 (12)	Sn1—C8—C9—C14	93.23 (18)
C8—Sn1—O1—C15	119.87 (12)	Sn1—C8—C9—C10	−81.55 (18)
C1—Sn1—O1—C15	−98.71 (12)	C14—C9—C10—C11	0.1 (3)
Cl1—Sn1—O1—C15	13.0 (2)	C8—C9—C10—C11	175.01 (17)
C8—Sn1—N2—C19	−94.25 (14)	C9—C10—C11—C12	0.6 (3)
C1—Sn1—N2—C19	75.77 (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—C19	170.83 (13)	C12—C13—C14—C9	0.9 (3)
N2—Sn1—C1—C2	−1.11 (14)	C10—C9—C14—C13	−0.8 (3)
C8—Sn1—C1—C2	163.69 (12)	C8—C9—C14—C13	−175.65 (18)
O1—Sn1—C1—C2	73.91 (13)	Sn1—O1—C15—C16	170.06 (16)
Cl1—Sn1—C1—C2	−90.98 (12)	Sn1—O1—C15—C19	−8.36 (19)
Sn1—C1—C2—C7	85.78 (19)	O1—C15—C16—C17	−177.14 (17)
Sn1—C1—C2—C3	−90.42 (18)	C19—C15—C16—C17	1.2 (3)
C7—C2—C3—C4	−1.1 (3)	C15—C16—C17—C18	−1.6 (3)
C1—C2—C3—C4	175.23 (18)	C16—C17—C18—N1	0.2 (3)
C2—C3—C4—C5	0.6 (3)	C19—N1—C18—C17	1.7 (3)
C3—C4—C5—C6	0.4 (3)	Sn1—N2—C19—N1	−169.87 (13)
C4—C5—C6—C7	−0.8 (3)	Sn1—N2—C19—C15	9.3 (2)
C5—C6—C7—C2	0.3 (3)	C18—N1—C19—N2	177.05 (17)
C3—C2—C7—C6	0.7 (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—N1	179.10 (15)
O1—Sn1—C8—C9	−82.56 (12)	C16—C15—C19—N1	0.6 (3)
Cl1—Sn1—C8—C9	81.86 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88 (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]
M_r	445.50
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	133
a, b, c (Å)	11.0457 (1), 16.8447 (2), 19.1227 (2)
V (Å³)	3558.00 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.59
Crystal size (mm)	0.20 × 0.05 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.640, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	32398, 4086, 3434
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.054, 1.01
No. of reflections	4086
No. of parameters	225
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88 (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

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