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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m390.
Published online 2010 March 10. doi:  10.1107/S1600536810008561
PMCID: PMC2983849

2-(Methoxy­carbon­yl)quinolinium tetra­chlorido(quinoline-2-carboxyl­ato-κ2 N,O)stannate(IV) methanol solvate

Abstract

In the title salt, (C11H10NO2)[SnCl4(C10H6NO2)]·CH3OH, the Sn atom is chelated by the quinolincarboxyl­ate unit and it exists in a distorted octa­hedral coordination geometry. The cation is linked to the solvent mol­ecule by an N—H(...)O hydrogen bond; the solvent mol­ecule is linked to the anion by an O—H(...)O hydrogen bond.

Related literature

For the structure of 2-(ethoxy­carbon­yl)quinolinium n-butyl­trichlorido(quinolin-2-carboxyl­ato)stannate(IV), see: Wang et al. (2008 [triangle]).

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Object name is e-66-0m390-scheme1.jpg

Experimental

Crystal data

  • (C11H10NO2)[SnCl4(C10H6NO2)]·CH4O
  • M r = 652.89
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m390-efi1.jpg
  • a = 8.4109 (4) Å
  • b = 33.2728 (16) Å
  • c = 10.0241 (5) Å
  • β = 112.8616 (6)°
  • V = 2584.9 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.44 mm−1
  • T = 293 K
  • 0.35 × 0.25 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.633, T max = 0.813
  • 24727 measured reflections
  • 5924 independent reflections
  • 5288 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.104
  • S = 1.17
  • 5924 reflections
  • 317 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.38 e Å−3
  • Δρmin = −1.15 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); 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 global, I. DOI: 10.1107/S1600536810008561/bt5208sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008561/bt5208Isup2.hkl

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

Acknowledgments

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Quinolin-2-carboxylic acid forms a number of compounds with organotin(IV) systems in which the deprotonated anion N,O-chelates to the tin atom. Such organotin carboxylates are conveniently synthesized by the reaction of an organotin chloride with the sodium salt of the carboxylic acid. Curiously, the reaction of sodium quinolin-2-carboxylate with n-butyltin trichloride furnishes the n-butyltrichlorido(quinolincarboxylato)stannate anion, whose charge is balanced by an ethyl quinoliniumcarboxylate cation (Wang et al., 2008). The ethyl unit arises from the ethanol solvent used in the synthesis.

In our hands, the reaction of quinolin-2-carboxylic acid with stannic chloride has yielded a similar salt, which crystallizes as a methanol solvate (Scheme I, Fig. 1). The solvent is also involved in the esterification of the acid to furnish the cation. The cation is linked to the solvent molecule by an N–H···O hydrogen bond; the solvent molecule is linked to the anion by an O–H···O hydrogen bond.

Experimental

Stannic chloride pentahydrate (1 mmol, 0.350 g) and quinaldic acid (2 mmol, 0.173 g) were dissolved in dry methanol. The solvent was allowed to evaporate to afford colorless crystals after 1 week.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The nitrogen- and oxygen-bound ones were located in a difference Fourier map, and were refined isotropically with distance restraints of N–H = O–H 0.86±0.01 Å.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of [C11H10NO2][SnCl4(C10H6NO2)].CH3OH; ellipsoids are drawn at the 50% probability level and H atoms are of arbitrary radius. Hydrogen bonds are drawn as dashed lines.

Crystal data

(C11H10NO2)[SnCl4(C10H6NO2)]·CH4OF(000) = 1296
Mr = 652.89Dx = 1.678 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9921 reflections
a = 8.4109 (4) Åθ = 2.3–28.1°
b = 33.2728 (16) ŵ = 1.44 mm1
c = 10.0241 (5) ÅT = 293 K
β = 112.8616 (6)°Wedge, colorless
V = 2584.9 (2) Å30.35 × 0.25 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer5924 independent reflections
Radiation source: fine-focus sealed tube5288 reflections with I > 2σ(I)
graphiteRint = 0.026
ω scansθmax = 27.5°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.633, Tmax = 0.813k = −43→42
24727 measured reflectionsl = −13→13

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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.17w = 1/[σ2(Fo2) + (0.0423P)2 + 3.5411P] where P = (Fo2 + 2Fc2)/3
5924 reflections(Δ/σ)max = 0.001
317 parametersΔρmax = 0.38 e Å3
2 restraintsΔρmin = −1.15 e Å3

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

xyzUiso*/Ueq
Sn10.77625 (3)0.625981 (7)0.62161 (2)0.03525 (9)
Cl10.79773 (15)0.56055 (3)0.53317 (11)0.0513 (2)
Cl20.86453 (17)0.60335 (4)0.86654 (11)0.0633 (3)
Cl31.06377 (14)0.64544 (4)0.66027 (14)0.0661 (3)
Cl40.47849 (13)0.61972 (3)0.58488 (12)0.0492 (2)
O10.6997 (4)0.64512 (8)0.4078 (3)0.0419 (6)
O20.6522 (5)0.69652 (10)0.2599 (3)0.0665 (9)
O30.1333 (4)0.58105 (10)0.2844 (4)0.0573 (8)
O40.2708 (4)0.62339 (9)0.1913 (4)0.0566 (8)
O50.5646 (4)0.63000 (9)0.0768 (3)0.0476 (6)
N10.7356 (4)0.69426 (9)0.6318 (3)0.0388 (7)
N30.4799 (4)0.56215 (9)0.1803 (3)0.0376 (6)
C10.6875 (5)0.68256 (12)0.3810 (4)0.0439 (9)
C20.7133 (5)0.71104 (11)0.5058 (4)0.0408 (8)
C30.7086 (7)0.75223 (13)0.4836 (5)0.0591 (12)
H3A0.69190.76260.39300.071*
C40.7287 (7)0.77719 (13)0.5963 (5)0.0638 (13)
H40.72970.80490.58400.077*
C50.7481 (6)0.76113 (12)0.7317 (5)0.0505 (10)
C60.7654 (7)0.78527 (14)0.8525 (6)0.0676 (14)
H60.77100.81310.84550.081*
C70.7741 (8)0.76872 (16)0.9772 (6)0.0747 (16)
H70.78310.78511.05500.090*
C80.7696 (8)0.72689 (16)0.9909 (5)0.0726 (15)
H80.77430.71571.07740.087*
C90.7581 (7)0.70231 (14)0.8775 (5)0.0573 (12)
H90.75710.67460.88820.069*
C100.7480 (5)0.71862 (11)0.7467 (4)0.0421 (8)
C110.2513 (5)0.59121 (12)0.2346 (4)0.0423 (8)
C120.3641 (5)0.55578 (11)0.2379 (4)0.0412 (8)
C130.3513 (6)0.51870 (13)0.2949 (5)0.0530 (10)
H130.26860.51430.33370.064*
C140.4601 (7)0.48872 (13)0.2940 (5)0.0599 (12)
H140.45280.46390.33390.072*
C150.5835 (6)0.49474 (12)0.2337 (4)0.0503 (10)
C160.7009 (7)0.46501 (15)0.2295 (6)0.0681 (14)
H160.70100.43990.27030.082*
C170.8142 (7)0.47287 (17)0.1659 (6)0.0739 (16)
H170.89140.45310.16380.089*
C180.8150 (6)0.51091 (17)0.1030 (6)0.0671 (14)
H180.89170.51560.05840.081*
C190.7058 (5)0.54069 (14)0.1064 (5)0.0524 (10)
H190.70810.56560.06550.063*
C200.5903 (5)0.53305 (11)0.1727 (4)0.0418 (8)
C210.0198 (7)0.61294 (16)0.2925 (7)0.0707 (14)
H21A−0.06610.60200.32310.106*
H21B−0.03550.62510.19890.106*
H21C0.08590.63280.36090.106*
C220.4323 (7)0.64239 (17)−0.0535 (5)0.0680 (13)
H22A0.32220.6360−0.05110.102*
H22B0.44450.6288−0.13340.102*
H22C0.44000.6709−0.06490.102*
H30.490 (6)0.5852 (7)0.145 (4)0.051 (13)*
H50.589 (7)0.6495 (10)0.135 (4)0.069 (16)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sn10.03944 (14)0.03703 (14)0.02901 (13)0.00101 (10)0.01300 (10)0.00026 (9)
Cl10.0677 (7)0.0394 (5)0.0486 (5)0.0063 (4)0.0244 (5)−0.0038 (4)
Cl20.0838 (8)0.0711 (7)0.0352 (5)0.0275 (6)0.0232 (5)0.0130 (5)
Cl30.0402 (6)0.0898 (9)0.0675 (7)−0.0076 (5)0.0202 (5)−0.0077 (6)
Cl40.0413 (5)0.0480 (5)0.0587 (6)−0.0016 (4)0.0200 (4)0.0033 (4)
O10.0560 (16)0.0409 (14)0.0290 (12)−0.0004 (12)0.0168 (11)−0.0010 (10)
O20.113 (3)0.0531 (18)0.0342 (15)−0.0056 (18)0.0291 (17)0.0064 (13)
O30.0554 (18)0.0594 (19)0.071 (2)−0.0112 (14)0.0394 (16)−0.0129 (15)
O40.067 (2)0.0469 (17)0.067 (2)0.0100 (14)0.0382 (17)0.0064 (14)
O50.0541 (17)0.0469 (16)0.0389 (14)−0.0048 (13)0.0151 (13)−0.0037 (12)
N10.0468 (17)0.0349 (16)0.0379 (16)−0.0054 (13)0.0199 (14)−0.0032 (12)
N30.0431 (17)0.0348 (16)0.0344 (15)−0.0011 (13)0.0147 (13)−0.0012 (12)
C10.054 (2)0.046 (2)0.0339 (18)−0.0029 (17)0.0194 (17)0.0027 (15)
C20.050 (2)0.0383 (19)0.0363 (18)−0.0022 (16)0.0187 (16)0.0012 (15)
C30.089 (4)0.043 (2)0.050 (2)−0.006 (2)0.032 (2)0.0099 (19)
C40.096 (4)0.034 (2)0.067 (3)−0.006 (2)0.039 (3)−0.002 (2)
C50.064 (3)0.036 (2)0.058 (2)−0.0072 (18)0.031 (2)−0.0069 (18)
C60.096 (4)0.041 (2)0.078 (3)−0.011 (2)0.046 (3)−0.021 (2)
C70.111 (5)0.063 (3)0.070 (3)−0.015 (3)0.057 (3)−0.030 (3)
C80.114 (5)0.069 (3)0.055 (3)−0.018 (3)0.055 (3)−0.016 (2)
C90.089 (3)0.045 (2)0.051 (2)−0.012 (2)0.042 (2)−0.0110 (19)
C100.052 (2)0.0368 (19)0.043 (2)−0.0080 (16)0.0240 (18)−0.0077 (15)
C110.043 (2)0.046 (2)0.0396 (19)−0.0044 (16)0.0181 (17)−0.0102 (16)
C120.045 (2)0.040 (2)0.0386 (19)−0.0048 (16)0.0167 (16)−0.0045 (15)
C130.064 (3)0.044 (2)0.056 (2)−0.010 (2)0.028 (2)0.0029 (19)
C140.083 (3)0.036 (2)0.058 (3)−0.007 (2)0.024 (2)0.0033 (19)
C150.059 (3)0.037 (2)0.043 (2)0.0062 (18)0.0070 (19)−0.0042 (16)
C160.078 (3)0.045 (3)0.064 (3)0.018 (2)0.009 (3)−0.006 (2)
C170.062 (3)0.070 (3)0.073 (3)0.028 (3)0.008 (3)−0.017 (3)
C180.046 (3)0.083 (4)0.068 (3)0.009 (2)0.018 (2)−0.024 (3)
C190.045 (2)0.058 (3)0.054 (2)0.0022 (19)0.0180 (19)−0.011 (2)
C200.042 (2)0.0378 (19)0.0391 (19)0.0025 (15)0.0087 (16)−0.0082 (15)
C210.061 (3)0.075 (3)0.093 (4)−0.003 (2)0.048 (3)−0.024 (3)
C220.086 (4)0.077 (3)0.043 (2)0.001 (3)0.027 (2)0.001 (2)

Geometric parameters (Å, °)

Sn1—O12.083 (2)C7—C81.400 (7)
Sn1—N12.305 (3)C7—H70.9300
Sn1—Cl12.3838 (10)C8—C91.373 (6)
Sn1—Cl32.3853 (11)C8—H80.9300
Sn1—Cl22.3937 (10)C9—C101.391 (6)
Sn1—Cl42.3947 (10)C9—H90.9300
O1—C11.270 (5)C11—C121.505 (5)
O2—C11.223 (4)C12—C131.382 (6)
O3—C111.317 (5)C13—C141.356 (7)
O3—C211.451 (6)C13—H130.9300
O4—C111.190 (5)C14—C151.404 (7)
O5—C221.409 (6)C14—H140.9300
O5—H50.842 (10)C15—C161.410 (6)
N1—C21.325 (5)C15—C201.425 (6)
N1—C101.379 (5)C16—C171.362 (8)
N3—C121.328 (5)C16—H160.9300
N3—C201.364 (5)C17—C181.415 (8)
N3—H30.860 (10)C17—H170.9300
C1—C21.517 (5)C18—C191.360 (6)
C2—C31.387 (6)C18—H180.9300
C3—C41.358 (6)C19—C201.397 (6)
C3—H3A0.9300C19—H190.9300
C4—C51.408 (6)C21—H21A0.9600
C4—H40.9300C21—H21B0.9600
C5—C61.413 (6)C21—H21C0.9600
C5—C101.423 (5)C22—H22A0.9600
C6—C71.342 (7)C22—H22B0.9600
C6—H60.9300C22—H22C0.9600
O1—Sn1—N175.66 (10)C8—C9—C10120.5 (4)
O1—Sn1—Cl186.24 (8)C8—C9—H9119.8
N1—Sn1—Cl1161.86 (8)C10—C9—H9119.8
O1—Sn1—Cl388.44 (8)N1—C10—C9121.0 (3)
N1—Sn1—Cl383.31 (9)N1—C10—C5119.9 (3)
Cl1—Sn1—Cl395.15 (4)C9—C10—C5119.0 (4)
O1—Sn1—Cl2179.45 (8)O4—C11—O3126.9 (4)
N1—Sn1—Cl2104.89 (8)O4—C11—C12122.5 (4)
Cl1—Sn1—Cl293.21 (4)O3—C11—C12110.6 (3)
Cl3—Sn1—Cl291.59 (5)N3—C12—C13120.7 (4)
O1—Sn1—Cl488.95 (8)N3—C12—C11115.3 (3)
N1—Sn1—Cl485.89 (8)C13—C12—C11123.9 (4)
Cl1—Sn1—Cl495.12 (4)C14—C13—C12119.5 (4)
Cl3—Sn1—Cl4169.21 (4)C14—C13—H13120.2
Cl2—Sn1—Cl491.12 (4)C12—C13—H13120.2
C1—O1—Sn1119.0 (2)C13—C14—C15120.8 (4)
C11—O3—C21116.3 (4)C13—C14—H14119.6
C22—O5—H5108 (4)C15—C14—H14119.6
C2—N1—C10119.0 (3)C16—C15—C14123.8 (5)
C2—N1—Sn1110.0 (2)C16—C15—C20118.0 (5)
C10—N1—Sn1130.7 (2)C14—C15—C20118.2 (4)
C12—N3—C20122.7 (3)C17—C16—C15120.3 (5)
C12—N3—H3122 (3)C17—C16—H16119.8
C20—N3—H3116 (3)C15—C16—H16119.8
O2—C1—O1123.4 (4)C16—C17—C18120.4 (4)
O2—C1—C2118.9 (4)C16—C17—H17119.8
O1—C1—C2117.6 (3)C18—C17—H17119.8
N1—C2—C3123.6 (4)C19—C18—C17121.3 (5)
N1—C2—C1116.4 (3)C19—C18—H18119.3
C3—C2—C1120.0 (3)C17—C18—H18119.3
C4—C3—C2119.0 (4)C18—C19—C20118.7 (5)
C4—C3—H3A120.5C18—C19—H19120.6
C2—C3—H3A120.5C20—C19—H19120.6
C3—C4—C5120.0 (4)N3—C20—C19120.8 (4)
C3—C4—H4120.0N3—C20—C15118.0 (4)
C5—C4—H4120.0C19—C20—C15121.2 (4)
C4—C5—C6123.1 (4)O3—C21—H21A109.5
C4—C5—C10118.3 (4)O3—C21—H21B109.5
C6—C5—C10118.6 (4)H21A—C21—H21B109.5
C7—C6—C5121.0 (4)O3—C21—H21C109.5
C7—C6—H6119.5H21A—C21—H21C109.5
C5—C6—H6119.5H21B—C21—H21C109.5
C6—C7—C8120.3 (4)O5—C22—H22A109.5
C6—C7—H7119.8O5—C22—H22B109.5
C8—C7—H7119.8H22A—C22—H22B109.5
C9—C8—C7120.5 (5)O5—C22—H22C109.5
C9—C8—H8119.8H22A—C22—H22C109.5
C7—C8—H8119.8H22B—C22—H22C109.5
N1—Sn1—O1—C18.4 (3)Sn1—N1—C10—C9−12.5 (6)
Cl1—Sn1—O1—C1−170.3 (3)C2—N1—C10—C5−4.1 (6)
Cl3—Sn1—O1—C1−75.1 (3)Sn1—N1—C10—C5168.4 (3)
Cl2—Sn1—O1—C1−169 (9)C8—C9—C10—N1−179.7 (5)
Cl4—Sn1—O1—C194.5 (3)C8—C9—C10—C5−0.6 (7)
O1—Sn1—N1—C2−10.0 (3)C4—C5—C10—N12.4 (7)
Cl1—Sn1—N1—C2−6.0 (5)C6—C5—C10—N1−178.4 (4)
Cl3—Sn1—N1—C280.1 (3)C4—C5—C10—C9−176.7 (5)
Cl2—Sn1—N1—C2170.0 (2)C6—C5—C10—C92.5 (7)
Cl4—Sn1—N1—C2−100.0 (3)C21—O3—C11—O4−2.7 (6)
O1—Sn1—N1—C10177.0 (3)C21—O3—C11—C12177.7 (4)
Cl1—Sn1—N1—C10−179.0 (2)C20—N3—C12—C130.6 (6)
Cl3—Sn1—N1—C10−92.9 (3)C20—N3—C12—C11−179.0 (3)
Cl2—Sn1—N1—C10−3.0 (3)O4—C11—C12—N3−4.2 (6)
Cl4—Sn1—N1—C1087.0 (3)O3—C11—C12—N3175.5 (3)
Sn1—O1—C1—O2176.1 (3)O4—C11—C12—C13176.2 (4)
Sn1—O1—C1—C2−5.7 (5)O3—C11—C12—C13−4.1 (5)
C10—N1—C2—C32.8 (6)N3—C12—C13—C141.0 (6)
Sn1—N1—C2—C3−171.2 (4)C11—C12—C13—C14−179.4 (4)
C10—N1—C2—C1−175.6 (3)C12—C13—C14—C15−1.1 (7)
Sn1—N1—C2—C110.4 (4)C13—C14—C15—C16179.8 (5)
O2—C1—C2—N1174.0 (4)C13—C14—C15—C20−0.5 (7)
O1—C1—C2—N1−4.2 (6)C14—C15—C16—C17178.4 (5)
O2—C1—C2—C3−4.5 (6)C20—C15—C16—C17−1.3 (7)
O1—C1—C2—C3177.3 (4)C15—C16—C17—C18−0.2 (8)
N1—C2—C3—C40.4 (8)C16—C17—C18—C191.2 (8)
C1—C2—C3—C4178.8 (4)C17—C18—C19—C20−0.5 (7)
C2—C3—C4—C5−2.1 (8)C12—N3—C20—C19177.7 (4)
C3—C4—C5—C6−178.5 (5)C12—N3—C20—C15−2.1 (5)
C3—C4—C5—C100.8 (8)C18—C19—C20—N3179.2 (4)
C4—C5—C6—C7176.3 (6)C18—C19—C20—C15−1.1 (6)
C10—C5—C6—C7−2.9 (8)C16—C15—C20—N3−178.3 (4)
C5—C6—C7—C81.3 (9)C14—C15—C20—N32.0 (6)
C6—C7—C8—C90.7 (10)C16—C15—C20—C192.0 (6)
C7—C8—C9—C10−1.0 (9)C14—C15—C20—C19−177.8 (4)
C2—N1—C10—C9175.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5···O20.84 (1)1.95 (1)2.785 (4)176 (5)
N3—H3···O50.86 (1)1.85 (2)2.693 (4)166 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5208).

References

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  • Westrip, S. P. (2010). publCIF In preparation.

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