metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-(Eth­oxy­carbon­yl)quinolinium butyl­tri­chlorido(quinoline-2-carboxyl­ato-κ2N,O)stannate(IV)

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China, and bAnalytical and Testing Center of Beihua University, 132013, People's Republic of China
*Correspondence e-mail: handongyin@163.com

(Received 18 November 2007; accepted 18 December 2007; online 4 January 2008)

In the title compound, (C12H12NO2)[Sn(C4H9)(C10H6NO2)Cl3], the Sn atom is coordinated by one O and one N atom of a quinolinium-2-carboxyl­ate anion, three Cl atoms and one butyl ligand within a distorted octa­hedron. Three C atoms of the butyl ligand are disordered and were refined using a split model; the site occupancies are 0.57 and 0.43. The NH group of the cation is involved in inter­molecular N—H⋯O hydrogen bonding.

Related literature

For related literature, see: Xie et al. (1991[Xie, Q. L., Li, S. H., Zhang, D. K., Zhang, Z. G. & Hu, J. M. (1991). Acta Chim. Sinica, 49, 723-728.]); Ma et al. (2006[Ma, C. L., Li, J. K., Zhang, R. F. & Wang, D. Q. (2006). J. Organomet. Chem. 691, 1713-1721.]).

[Scheme 1]

Experimental

Crystal data
  • (C12H12NO2)[Sn(C4H9)(C10H6NO2)Cl3]

  • Mr = 656.54

  • Monoclinic, P 21 /c

  • a = 13.6828 (18) Å

  • b = 11.0449 (15) Å

  • c = 18.598 (2) Å

  • β = 93.898 (2)°

  • V = 2804.1 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.23 mm−1

  • T = 293 (2) K

  • 0.43 × 0.25 × 0.11 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.620, Tmax = 0.876

  • 13504 measured reflections

  • 4942 independent reflections

  • 2884 reflections with I > 2σ(I)

  • Rint = 0.050

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.132

  • S = 1.00

  • 4942 reflections

  • 328 parameters

  • 15 restraints

  • H-atom parameters constrained

  • Δρmax = 0.64 e Å−3

  • Δρmin = −0.41 e Å−3

Table 1
Selected geometric parameters (Å, °)

Sn1—O1 2.079 (4)
Sn1—C11 2.142 (7)
Sn1—N1 2.371 (4)
Sn1—Cl2 2.4405 (18)
Sn1—Cl3 2.4482 (18)
Sn1—Cl1 2.4924 (16)
O1—Sn1—C11 172.6 (2)
O1—Sn1—N1 73.06 (16)
C11—Sn1—N1 107.7 (3)
O1—Sn1—Cl2 82.66 (12)
C11—Sn1—Cl2 96.4 (3)
N1—Sn1—Cl2 155.72 (13)
O1—Sn1—Cl3 87.93 (13)
C11—Sn1—Cl3 99.5 (2)
N1—Sn1—Cl3 84.64 (12)
Cl2—Sn1—Cl3 94.28 (6)
O1—Sn1—Cl1 83.87 (13)
C11—Sn1—Cl1 88.8 (2)
N1—Sn1—Cl1 84.22 (12)
Cl2—Sn1—Cl1 93.73 (6)
Cl3—Sn1—Cl1 167.71 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O2i 0.86 2.26 3.078 (7) 158
N2—H2⋯O4i 0.86 2.53 2.990 (6) 114
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a[Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a[Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Sheldrick, 1997b[Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Organotin esters of carboxylic acids are widely used as biocidesand fungicides and in industry as homogeneous catalysts(Q. L. Xie et al., 1991). As a part of our ongoing investigations in this field we have synthesized the title compound and determined its crystal structure. The crystal structure of the title compound consists of discrete [ethyl(quinolinium-2-carboxylate)] cations and discrete [trichloro-butyl-(quinoline-2-carboxylato)tin(IV)] anions (Fig. 1 and Table 1). The Sn atom is coordinated by one O and one N atom of a quinolinium-2-carboxylate anion, which acts as a chelate ligand, three chloro atoms and one carbon atom of the butyl ligand within a distorted octahedral environment. The Sn1—O1 distance of 2.079 (4)Å and the Sn1—N1 distance of 2.371 (4) Å are comparable to those in similar organotin carboxylates (C. L. Ma et al., 2006). The N—H H atom of the [ethyl(quinolinium-2-carboxylate)] cation is involved in intermolecular N—H···O hydrogen bonding to O2 of the [ethyl(quinolinium-2-carboxylate)] anion (Table 2). The N—H atom forms an additional very weak hydrogen bond to O4 of a second [ethyl(quinolinium-2-carboxylate)] anion.

Related literature top

For related literature, see: Xie et al. (1991); Ma et al. (2006).

Experimental top

The reaction was carried out under nitrogen atmosphere. Quinoline-2-carboxylic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to the solution of ethanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Butyltin trichloride (1 mmol) was added to the Schlenk flask and the reaction mixture was stirred for 12 h at 313 K.The solvent was removed from the clear under reduced pressure. The crew prodcut was recrystallized from a mixture of dichloromethane/methanol (1:1).(yield 76%; m.p. 466 K). Analysis calculated (%) for C26H27Cl3N2O4Sn (Mr = 656.54): C, 47.56; H, 4.14; N, 4.27. found: C, 47.49; H, 4.21; N, 4.32.

Refinement top

The C—H and N—H H atoms were positioned with idealized geometry and were refined isotropic Uiso(H) = 1.5 Ueq for methyl H atoms and Uiso(H) = 1.2 Ueq for all other H atoms using a riding model with with N—H = 0.86 Å and C—H = 0.93, 0.96 and 0.97 Å for aromatic, methyl and methylene H atoms, respectively, The carbon atoms C12, C13, and C14 of the butyl ligand are disordered and were refined using a split model. In the first refinements the site-occupancy factors were refined using fixed isotropic displacement parameters and in the final refinement they were fixed at 0.57 for C12, C13 and C14 and to 0.43 for C12', C13' and C14'. The atoms with higher occupancy were refined anisotropic and those of lower occupancy were refined only isotropic.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. Crystal structure of the title compound with labeling and displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity and the two orientations of the disordered butyl ligand is shown as closed and open lines.
2-(Ethoxycarbonyl)quinolinium butyltrichlorido(quinoline-2-carboxylato-κ2N,O)tin(IV) top
Crystal data top
(C12H12NO2)[Sn(C4H9)(C10H6NO2)Cl3]F(000) = 1320
Mr = 656.54Dx = 1.555 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.6828 (18) ÅCell parameters from 2742 reflections
b = 11.0449 (15) Åθ = 2.2–20.4°
c = 18.598 (2) ŵ = 1.23 mm1
β = 93.898 (2)°T = 293 K
V = 2804.1 (6) Å3Block, colourless
Z = 40.43 × 0.25 × 0.11 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4942 independent reflections
Radiation source: fine-focus sealed tube2884 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ϕ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1612
Tmin = 0.620, Tmax = 0.877k = 1313
13504 measured reflectionsl = 1822
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.064P)2]
where P = (Fo2 + 2Fc2)/3
4942 reflections(Δ/σ)max < 0.001
328 parametersΔρmax = 0.64 e Å3
15 restraintsΔρmin = 0.41 e Å3
Crystal data top
(C12H12NO2)[Sn(C4H9)(C10H6NO2)Cl3]V = 2804.1 (6) Å3
Mr = 656.54Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.6828 (18) ŵ = 1.23 mm1
b = 11.0449 (15) ÅT = 293 K
c = 18.598 (2) Å0.43 × 0.25 × 0.11 mm
β = 93.898 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4942 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2884 reflections with I > 2σ(I)
Tmin = 0.620, Tmax = 0.877Rint = 0.050
13504 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04615 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.00Δρmax = 0.64 e Å3
4942 reflectionsΔρmin = 0.41 e Å3
328 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Sn10.69831 (3)0.03081 (4)0.28168 (2)0.04929 (18)
Cl10.74131 (13)0.15041 (15)0.35719 (8)0.0612 (5)
Cl20.82158 (17)0.01177 (16)0.19623 (10)0.0823 (7)
Cl30.65882 (15)0.23171 (16)0.23224 (10)0.0769 (6)
O10.8168 (3)0.1091 (4)0.3402 (2)0.0581 (12)
O20.8843 (4)0.1604 (5)0.4467 (3)0.0805 (15)
N10.6386 (4)0.1089 (4)0.3890 (2)0.0458 (12)
C10.8125 (5)0.1382 (5)0.4063 (4)0.0512 (16)
C20.7123 (5)0.1434 (5)0.4343 (3)0.0470 (15)
C30.6989 (6)0.1831 (6)0.5037 (3)0.0617 (18)
H30.75260.20640.53390.074*
C40.6076 (6)0.1880 (6)0.5275 (4)0.072 (2)
H40.59830.21390.57420.087*
C50.5276 (5)0.1540 (6)0.4815 (4)0.0591 (18)
C60.5443 (5)0.1167 (5)0.4111 (3)0.0497 (16)
C70.4649 (5)0.0865 (7)0.3630 (4)0.076 (2)
H70.47550.06340.31610.092*
C80.3722 (6)0.0909 (8)0.3852 (5)0.093 (3)
H80.31950.07030.35330.112*
C90.3554 (7)0.1265 (8)0.4561 (6)0.093 (3)
H90.29210.12810.47140.111*
C100.4302 (7)0.1574 (7)0.5005 (5)0.082 (3)
H100.41780.18270.54680.099*
C110.5827 (6)0.0718 (7)0.2273 (4)0.093 (3)
H11A0.61060.14070.20370.111*0.57
H11B0.53960.10230.26250.111*0.57
H11C0.60170.15640.22880.111*0.43
H11D0.52490.06400.25440.111*0.43
C120.5211 (17)0.0064 (16)0.1694 (10)0.120 (6)*0.57
H12A0.48230.06440.19430.144*0.57
H12B0.56590.05160.14140.144*0.57
C130.4535 (16)0.0666 (17)0.1185 (10)0.144 (7)*0.57
H13A0.39990.10100.14330.173*0.57
H13B0.48870.13130.09620.173*0.57
C140.4166 (18)0.0265 (18)0.0631 (12)0.148 (9)*0.57
H14A0.37300.01180.02740.222*0.57
H14B0.47120.06060.04020.222*0.57
H14C0.38240.08950.08650.222*0.57
C12'0.553 (2)0.038 (3)0.1457 (10)0.147 (12)*0.43
H12C0.59560.02330.12710.176*0.43
H12D0.55020.10820.11430.176*0.43
C13'0.451 (2)0.011 (3)0.1610 (18)0.196 (16)*0.43
H13C0.45800.09260.18030.235*0.43
H13D0.42350.03900.19740.235*0.43
C14'0.379 (2)0.014 (3)0.0927 (17)0.155 (13)*0.43
H14D0.31720.04660.10480.232*0.43
H14E0.36940.06710.07460.232*0.43
H14F0.40570.06330.05640.232*0.43
O31.0771 (3)0.3148 (4)0.5369 (2)0.0624 (12)
O41.0959 (3)0.1229 (4)0.4993 (2)0.0598 (12)
N20.9935 (4)0.0470 (4)0.6118 (2)0.0461 (12)
H21.02160.00300.58440.055*
C151.0645 (5)0.1969 (6)0.5387 (3)0.0506 (16)
C161.0041 (4)0.1641 (5)0.5998 (3)0.0429 (14)
C170.9592 (5)0.2459 (6)0.6425 (3)0.0542 (17)
H170.96420.32840.63350.058 (18)*
C180.9077 (5)0.2060 (6)0.6975 (3)0.0593 (18)
H180.87960.26220.72720.07 (2)*
C190.8962 (5)0.0835 (5)0.7110 (3)0.0487 (15)
C200.9409 (5)0.0006 (5)0.6651 (3)0.0473 (16)
C210.9317 (5)0.1241 (6)0.6754 (3)0.0571 (18)
H210.96310.17850.64650.07 (2)*
C220.8756 (5)0.1650 (7)0.7282 (4)0.068 (2)
H220.86600.24770.73370.08 (2)*
C230.8330 (6)0.0833 (7)0.7743 (4)0.072 (2)
H230.79780.11290.81160.07 (2)*
C240.8416 (5)0.0365 (7)0.7658 (4)0.067 (2)
H240.81150.08900.79660.10 (3)*
C251.1392 (6)0.3627 (7)0.4834 (4)0.084 (2)
H25A1.10960.34820.43530.101*
H25B1.20280.32360.48760.101*
C261.1503 (7)0.4927 (7)0.4965 (5)0.107 (3)
H26A1.08690.53010.49450.161*
H26B1.18840.52760.46030.161*
H26C1.18290.50560.54320.161*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sn10.0565 (3)0.0507 (3)0.0415 (3)0.0008 (2)0.00965 (19)0.0027 (2)
Cl10.0690 (12)0.0592 (10)0.0573 (10)0.0150 (9)0.0176 (8)0.0050 (8)
Cl20.1224 (18)0.0624 (11)0.0690 (11)0.0002 (11)0.0563 (12)0.0073 (9)
Cl30.0952 (16)0.0634 (11)0.0731 (12)0.0124 (11)0.0122 (10)0.0132 (9)
O10.048 (3)0.071 (3)0.058 (3)0.000 (2)0.015 (2)0.012 (2)
O20.053 (3)0.109 (4)0.079 (3)0.004 (3)0.007 (3)0.020 (3)
N10.042 (3)0.049 (3)0.047 (3)0.009 (3)0.008 (2)0.005 (2)
C10.047 (4)0.049 (4)0.058 (4)0.001 (3)0.008 (3)0.004 (3)
C20.050 (4)0.046 (4)0.046 (4)0.004 (3)0.008 (3)0.004 (3)
C30.073 (5)0.066 (5)0.046 (4)0.000 (4)0.005 (4)0.009 (3)
C40.098 (7)0.067 (5)0.055 (4)0.011 (5)0.023 (5)0.017 (4)
C50.065 (5)0.053 (4)0.063 (4)0.016 (4)0.031 (4)0.004 (3)
C60.047 (4)0.053 (4)0.052 (4)0.009 (3)0.017 (3)0.009 (3)
C70.052 (5)0.106 (6)0.072 (5)0.000 (5)0.010 (4)0.009 (4)
C80.042 (5)0.129 (7)0.107 (7)0.008 (5)0.002 (5)0.038 (6)
C90.058 (6)0.096 (7)0.128 (8)0.024 (5)0.044 (6)0.030 (6)
C100.080 (7)0.068 (5)0.105 (7)0.027 (5)0.047 (6)0.016 (5)
C110.098 (7)0.083 (5)0.093 (6)0.010 (5)0.028 (5)0.015 (5)
O30.075 (3)0.054 (3)0.061 (3)0.003 (3)0.027 (2)0.011 (2)
O40.065 (3)0.069 (3)0.047 (3)0.000 (3)0.012 (2)0.009 (2)
N20.048 (3)0.049 (3)0.042 (3)0.002 (3)0.006 (2)0.004 (2)
C150.043 (4)0.064 (5)0.045 (4)0.004 (3)0.002 (3)0.006 (3)
C160.037 (4)0.044 (4)0.048 (4)0.001 (3)0.007 (3)0.004 (3)
C170.056 (4)0.044 (4)0.064 (4)0.001 (3)0.020 (3)0.007 (3)
C180.071 (5)0.048 (4)0.062 (4)0.006 (4)0.028 (4)0.001 (3)
C190.053 (4)0.044 (4)0.050 (4)0.001 (3)0.011 (3)0.000 (3)
C200.049 (4)0.048 (4)0.045 (4)0.002 (3)0.004 (3)0.007 (3)
C210.070 (5)0.044 (4)0.057 (4)0.003 (4)0.005 (4)0.003 (3)
C220.078 (6)0.057 (5)0.069 (5)0.009 (4)0.003 (4)0.012 (4)
C230.088 (6)0.070 (5)0.060 (5)0.006 (5)0.023 (4)0.018 (4)
C240.074 (5)0.064 (5)0.066 (5)0.001 (4)0.027 (4)0.006 (4)
C250.100 (7)0.072 (5)0.087 (6)0.021 (5)0.045 (5)0.012 (4)
C260.127 (9)0.102 (7)0.098 (6)0.028 (6)0.042 (6)0.026 (5)
Geometric parameters (Å, º) top
Sn1—O12.079 (4)C14—H14B0.9600
Sn1—C112.142 (7)C14—H14C0.9600
Sn1—N12.371 (4)C12'—C13'1.547 (17)
Sn1—Cl22.4405 (18)C12'—H12C0.9700
Sn1—Cl32.4482 (18)C12'—H12D0.9700
Sn1—Cl12.4924 (16)C13'—C14'1.555 (17)
O1—C11.275 (7)C13'—H13C0.9700
O2—C11.221 (7)C13'—H13D0.9700
N1—C21.325 (7)C14'—H14D0.9600
N1—C61.383 (7)C14'—H14E0.9600
C1—C21.500 (8)C14'—H14F0.9600
C2—C31.386 (8)O3—C151.315 (7)
C3—C41.355 (9)O3—C251.452 (7)
C3—H30.9300O4—C151.197 (7)
C4—C51.394 (10)N2—C161.322 (7)
C4—H40.9300N2—C201.363 (7)
C5—C101.403 (10)N2—H20.8600
C5—C61.407 (8)C15—C161.494 (8)
C6—C71.398 (9)C16—C171.375 (8)
C7—C81.361 (10)C17—C181.355 (8)
C7—H70.9300C17—H170.9298
C8—C91.411 (11)C18—C191.387 (8)
C8—H80.9300C18—H180.9300
C9—C101.316 (11)C19—C241.403 (8)
C9—H90.9300C19—C201.419 (8)
C10—H100.9300C20—C211.397 (8)
C11—C121.579 (13)C21—C221.364 (8)
C11—C12'1.587 (16)C21—H210.9305
C11—H11A0.9700C22—C231.398 (9)
C11—H11B0.9700C22—H220.9295
C11—H11C0.9700C23—C241.339 (9)
C11—H11D0.9700C23—H230.9303
C12—C131.511 (14)C24—H240.9306
C12—H12A0.9700C25—C261.463 (9)
C12—H12B0.9700C25—H25A0.9699
C13—C141.518 (15)C25—H25B0.9699
C13—H13A0.9700C26—H26A0.9600
C13—H13B0.9700C26—H26B0.9600
C14—H14A0.9600C26—H26C0.9600
O1—Sn1—C11172.6 (2)C14—C13—H13A111.2
O1—Sn1—N173.06 (16)C12—C13—H13B111.2
C11—Sn1—N1107.7 (3)C14—C13—H13B111.2
O1—Sn1—Cl282.66 (12)H13A—C13—H13B109.1
C11—Sn1—Cl296.4 (3)C13—C14—H14A109.5
N1—Sn1—Cl2155.72 (13)C13—C14—H14B109.5
O1—Sn1—Cl387.93 (13)H14A—C14—H14B109.5
C11—Sn1—Cl399.5 (2)C13—C14—H14C109.5
N1—Sn1—Cl384.64 (12)H14A—C14—H14C109.5
Cl2—Sn1—Cl394.28 (6)H14B—C14—H14C109.5
O1—Sn1—Cl183.87 (13)C13'—C12'—C1194.6 (19)
C11—Sn1—Cl188.8 (2)C13'—C12'—H12C112.8
N1—Sn1—Cl184.22 (12)C11—C12'—H12C112.8
Cl2—Sn1—Cl193.73 (6)C13'—C12'—H12D112.8
Cl3—Sn1—Cl1167.71 (6)C11—C12'—H12D112.8
C1—O1—Sn1121.6 (4)H12C—C12'—H12D110.3
C2—N1—C6118.7 (5)C12'—C13'—C14'113 (3)
C2—N1—Sn1110.4 (4)C12'—C13'—H13C109.0
C6—N1—Sn1130.8 (4)C14'—C13'—H13C109.0
O2—C1—O1123.7 (6)C12'—C13'—H13D109.0
O2—C1—C2119.7 (6)C14'—C13'—H13D109.0
O1—C1—C2116.6 (6)H13C—C13'—H13D107.8
N1—C2—C3122.6 (6)C13'—C14'—H14D109.5
N1—C2—C1116.2 (5)C13'—C14'—H14E109.5
C3—C2—C1121.2 (6)H14D—C14'—H14E109.5
C4—C3—C2120.0 (7)C13'—C14'—H14F109.5
C4—C3—H3120.0H14D—C14'—H14F109.5
C2—C3—H3120.0H14E—C14'—H14F109.5
C3—C4—C5119.4 (6)C15—O3—C25117.5 (5)
C3—C4—H4120.3C16—N2—C20124.1 (5)
C5—C4—H4120.3C16—N2—H2118.0
C4—C5—C10123.9 (7)C20—N2—H2118.0
C4—C5—C6118.8 (6)O4—C15—O3127.4 (6)
C10—C5—C6117.3 (7)O4—C15—C16122.7 (6)
N1—C6—C7119.7 (6)O3—C15—C16109.9 (6)
N1—C6—C5120.5 (6)N2—C16—C17119.1 (5)
C7—C6—C5119.8 (6)N2—C16—C15116.0 (5)
C8—C7—C6119.8 (7)C17—C16—C15124.9 (6)
C8—C7—H7120.1C18—C17—C16119.9 (6)
C6—C7—H7120.1C18—C17—H17120.2
C7—C8—C9120.5 (8)C16—C17—H17119.9
C7—C8—H8119.8C17—C18—C19121.7 (6)
C9—C8—H8119.8C17—C18—H18119.1
C10—C9—C8119.4 (8)C19—C18—H18119.2
C10—C9—H9120.3C18—C19—C24124.4 (6)
C8—C9—H9120.3C18—C19—C20117.5 (6)
C9—C10—C5123.1 (8)C24—C19—C20118.1 (6)
C9—C10—H10118.4N2—C20—C21121.8 (6)
C5—C10—H10118.4N2—C20—C19117.7 (5)
C12—C11—Sn1112.1 (8)C21—C20—C19120.4 (6)
C12'—C11—Sn1117.2 (12)C22—C21—C20119.1 (6)
C12—C11—H11A109.2C22—C21—H21120.5
C12'—C11—H11A80.4C20—C21—H21120.5
Sn1—C11—H11A109.2C21—C22—C23120.4 (7)
C12—C11—H11B109.2C21—C22—H22119.7
C12'—C11—H11B126.9C23—C22—H22119.9
Sn1—C11—H11B109.2C24—C23—C22121.5 (7)
H11A—C11—H11B107.9C24—C23—H23119.3
C12—C11—H11C132.5C22—C23—H23119.2
C12'—C11—H11C107.6C23—C24—C19120.4 (7)
Sn1—C11—H11C108.0C23—C24—H24119.8
H11B—C11—H11C79.6C19—C24—H24119.8
C12—C11—H11D83.6O3—C25—C26107.6 (6)
C12'—C11—H11D108.3O3—C25—H25A110.2
Sn1—C11—H11D108.0C26—C25—H25A110.3
H11A—C11—H11D131.6O3—C25—H25B110.3
H11C—C11—H11D107.3C26—C25—H25B110.0
C13—C12—C11114.3 (14)H25A—C25—H25B108.5
C13—C12—H12A108.7C25—C26—H26A109.5
C11—C12—H12A108.7C25—C26—H26B109.5
C13—C12—H12B108.7H26A—C26—H26B109.5
C11—C12—H12B108.7C25—C26—H26C109.5
H12A—C12—H12B107.6H26A—C26—H26C109.5
C12—C13—C14103.0 (16)H26B—C26—H26C109.5
C12—C13—H13A111.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.263.078 (7)158
N2—H2···O4i0.862.532.990 (6)114
Symmetry code: (i) x+2, y, z+1.

Experimental details

Crystal data
Chemical formula(C12H12NO2)[Sn(C4H9)(C10H6NO2)Cl3]
Mr656.54
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.6828 (18), 11.0449 (15), 18.598 (2)
β (°) 93.898 (2)
V3)2804.1 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.23
Crystal size (mm)0.43 × 0.25 × 0.11
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.620, 0.877
No. of measured, independent and
observed [I > 2σ(I)] reflections
13504, 4942, 2884
Rint0.050
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.132, 1.00
No. of reflections4942
No. of parameters328
No. of restraints15
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.64, 0.41

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected geometric parameters (Å, º) top
Sn1—O12.079 (4)Sn1—Cl22.4405 (18)
Sn1—C112.142 (7)Sn1—Cl32.4482 (18)
Sn1—N12.371 (4)Sn1—Cl12.4924 (16)
O1—Sn1—C11172.6 (2)N1—Sn1—Cl384.64 (12)
O1—Sn1—N173.06 (16)Cl2—Sn1—Cl394.28 (6)
C11—Sn1—N1107.7 (3)O1—Sn1—Cl183.87 (13)
O1—Sn1—Cl282.66 (12)C11—Sn1—Cl188.8 (2)
C11—Sn1—Cl296.4 (3)N1—Sn1—Cl184.22 (12)
N1—Sn1—Cl2155.72 (13)Cl2—Sn1—Cl193.73 (6)
O1—Sn1—Cl387.93 (13)Cl3—Sn1—Cl1167.71 (6)
C11—Sn1—Cl399.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.263.078 (7)158.4
N2—H2···O4i0.862.532.990 (6)114.2
Symmetry code: (i) x+2, y, z+1.
 

Acknowledgements

We thank the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support.

References

First citationMa, C. L., Li, J. K., Zhang, R. F. & Wang, D. Q. (2006). J. Organomet. Chem. 691, 1713–1721.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationXie, Q. L., Li, S. H., Zhang, D. K., Zhang, Z. G. & Hu, J. M. (1991). Acta Chim. Sinica, 49, 723–728.  CAS Google Scholar

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