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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m272.
Published online 2008 January 4. doi:  10.1107/S1600536807067566
PMCID: PMC2960164

2-(Ethoxy­carbon­yl)quinolinium butyl­trichlorido(quinoline-2-carboxyl­ato-κ2 N,O)stannate(IV)

Abstract

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 [triangle]); Ma et al. (2006 [triangle]).

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Object name is e-64-0m272-scheme1.jpg

Experimental

Crystal data

  • (C12H12NO2)[Sn(C4H9)(C10H6NO2)Cl3]
  • M r = 656.54
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m272-efi1.jpg
  • 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 [triangle]) T min = 0.620, T max = 0.876
  • 13504 measured reflections
  • 4942 independent reflections
  • 2884 reflections with I > 2σ(I)
  • R int = 0.050

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 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

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

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067566/nc2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067566/nc2083Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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.

Crystal data

(C12H12NO2)[Sn(C4H9)(C10H6NO2)Cl3]F000 = 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 = 2.2–20.4º
c = 18.598 (2) ŵ = 1.23 mm1
β = 93.898 (2)ºT = 293 (2) K
V = 2804.1 (6) Å3Block, colourless
Z = 40.43 × 0.25 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer4942 independent reflections
Radiation source: fine-focus sealed tube2884 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.050
T = 293(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −16→12
Tmin = 0.620, Tmax = 0.877k = −13→13
13504 measured reflectionsl = −18→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.132  w = 1/[σ2(Fo2) + (0.064P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4942 reflectionsΔρmax = 0.64 e Å3
328 parametersΔρmin = −0.41 e Å3
15 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

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)
H11A0.6106−0.14070.20370.111*0.57
H11B0.5396−0.10230.26250.111*0.57
H11C0.6017−0.15640.22880.111*0.43
H11D0.5249−0.06400.25440.111*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
H13A0.3999−0.10100.14330.173*0.57
H13B0.4887−0.13130.09620.173*0.57
C140.4166 (18)0.0265 (18)0.0631 (12)0.148 (9)*0.57
H14A0.3730−0.01180.02740.222*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
H12D0.5502−0.10820.11430.176*0.43
C13'0.451 (2)0.011 (3)0.1610 (18)0.196 (16)*0.43
H13C0.45800.09260.18030.235*0.43
H13D0.4235−0.03900.19740.235*0.43
C14'0.379 (2)0.014 (3)0.0927 (17)0.155 (13)*0.43
H14D0.31720.04660.10480.232*0.43
H14E0.3694−0.06710.07460.232*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)
H21.0216−0.00300.58440.055*
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)
H210.9631−0.17850.64650.07 (2)*
C220.8756 (5)−0.1650 (7)0.7282 (4)0.068 (2)
H220.8660−0.24770.73370.08 (2)*
C230.8330 (6)−0.0833 (7)0.7743 (4)0.072 (2)
H230.7978−0.11290.81160.07 (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)

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, °)

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, °)

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 codes: (i) −x+2, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2083).

References

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  • Xie, Q. L., Li, S. H., Zhang, D. K., Zhang, Z. G. & Hu, J. M. (1991). Acta Chim. Sinica, 49, 723–728.

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