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

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 68| Part 5| May 2012| Page o1371

1,1,2,2-Tetra­kis(di­methyl­amino)­ethane-1,2-diium bis­­(tetra­phenyl­borate) acetone disolvate

aInstitut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany, and bFakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany
*Correspondence e-mail: willi.kantlehner@htw-aalen.de

(Received 29 March 2012; accepted 5 April 2012; online 13 April 2012)

The title compound, C10H24N42+·2C24H20B·2C3H6O, crystallizes with two acetone solvent mol­ecules per asymmetric unit. In the dication, both amidinium units are twisted about the central C—C single bond by 63.8 (3)° and the positive charges are delocalized over both N—C—N planes.

Related literature

For the crystal structure of tetra­kis­(dimethyl­amino)­ethyl­ene (TDAE), see: Bock et al. (1991[Bock, H., Borrmann, H., Havlas, Z., Oberhammer, H., Ruppert, K. & Simon, A. (1991). Angew. Chem. Int. Ed. 30, 1678-1681.]). For the synthesis of octa­methyl­oxamidinium salts with different anions, see: Wiberg (1968[Wiberg, N. (1968). Angew. Chem. Int. Ed. 10, 766-779.]). For the synthesis and crystal structures of (TDAE)Cl2 and (TDAE)Br2, see: Bock et al. (1989[Bock, H., Ruppert, K., Merzweiler, K., Fenske, D. & Goesmann, H. (1989). Angew. Chem. Int. Ed. 28, 1684-1685.]). For the synthesis and crystal structure of (TDAE)(SCF3)2, see: Kolomeitsev et al. (2000[Kolomeitsev, A., Medébielle, M., Kirsch, P., Lork, E. & Röschenthaler, H. (2000). J. Chem. Soc. Perkin Trans. 1, pp. 2183-2185.]). For the crystal structure of (TDAE)(PF6)2, see: Elbl-Weiser et al. (1990[Elbl-Weiser, K., Krieger, C. & Staab, H. A. (1990). Angew. Chem. Int. Ed. 29, 211-213.]). For the synthesis and crystal structure of N,N,N′,N′,N′′,N′′,N′′′,N′′′-octa­methyl-(but-2-yne) bis­(amidin­ium) bis­(tetra­fluoro­borate), see: Drandarov et al. (2012[Drandarov, K., Tiritiris, I., Wassiljew, O., Siehl, H.-U. & Kantlehner, W. (2012). Chem. Eur. J. Accepted.]). For N,N,N′,N′,N′′,N′′,N′′′,N′′′-octa­methyl-(but-2-yne) bis­(amidin­ium) bis­(tetra­phenyl­borate), see: Kress et al. (2012[Kress, R., Tiritiris, I. & Kantlehner, W. (2012). Unpublished results.]).

[Scheme 1]

Experimental

Crystal data
  • C10H24N42+·2C24H20B·2C3H6O

  • Mr = 954.91

  • Orthorhombic, P c a 21

  • a = 30.0601 (9) Å

  • b = 9.9321 (3) Å

  • c = 18.2054 (6) Å

  • V = 5435.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 100 K

  • 0.30 × 0.24 × 0.18 mm

Data collection
  • Bruker Kappa APEXII DUO diffractometer

  • 36726 measured reflections

  • 4983 independent reflections

  • 4058 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.109

  • S = 1.05

  • 4983 reflections

  • 661 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.30 e Å−3

Data collection: APEX2, (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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; molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, D-53002 Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

By oxidizing tetrakis(dimethylamino)ethylene (TDAE) with elemental halogens in organic solvents, the octamethyloxamidinium ion (TDAE)2+ is formed (Wiberg, 1968). This is also associated with major structural changes. In the here studied bis(tetraphenylborate) salt (Fig. 1), the single bond between C1 and C2 is clearly characterized by a length of 1.498 (5) Å and the C–N bond lengths are equal with 1.309 (4) to 1.330 (4) Å, indicating double bond character. The bonds between the N atoms and the terminal C-methyl groups, all have values close to a typical single bond (1.463 (5)–1.479 (5) Å). The sums of angles around the central C1, C2 and the N atoms are all close to 360°. As a consequence of the two-electron oxidation, the presence of four planar dimethylamino groups and a nearly perfect delocalization of each positive charge in the amidinium systems is observed. The charges are distributed in the dication between the dimethylamino groups. The planes built up from both amidinium units (N1/C1/N2 and N3/C2/N4) are twisted to each other by 63.8 (3)°. Similar arrangements have been observed in the crystal structures of (TDAE)Cl2 (Bock et al., 1989), (TDAE)Br2 (Bock et al., 1989), (TDAE)(SCF3)2 (Kolomeitsev et al., 2000) and (TDAE)(PF6)2 (Elbl-Weiser et al., 1990). In contrast to the previously mentioned salts, which are all colourless, the title compound is yellow coloured. The same phenomenon was observed when the colours of N,N,N',N',N'',N'', N''',N'''-octamethyl-(but-2-yne)-bis(amidinium)- bis(tetrafluoroborate) (Drandarov et al., 2012) and -bis(tetraphenylborate) (Kress et al., 2012) were compared.

Related literature top

For the crystal structure of tetrakis(dimethylamino)ethylene (TDAE), see: Bock et al. (1991). For the synthesis of octamethyloxamidinium salts with different anions, see: Wiberg (1968). For the synthesis and crystal structures of (TDAE)Cl2 and (TDAE)Br2, see: Bock et al. (1989). For the synthesis and crystal structure of (TDAE)(SCF3)2, see: Kolomeitsev et al. (2000). For the crystal structure of (TDAE)(PF6)2, see: Elbl-Weiser et al. (1990). For the synthesis and crystal structure of N,N,N',N',N'',N'',N''',N'''-octamethyl-(but-2-yne)-bis(amidinium)- bis(tetrafluoroborate), see: Drandarov et al. (2012). For N,N,N',N',N'',N'',N''',N'''-octamethyl-(but-2-yne)-bis(amidinium)-bis(tetraphenylborate), see: Kress et al. (2012).

Experimental top

The title compound was prepared by reaction of sodium tetraphenylborate with N,N,N',N',N'',N'',N''', N'''-octamethyloxamidinium dichloride in acetonitrile at room temperature. Yellow single crystals were obtained by slow evaporation of an acetone solution at room temperature.

Refinement top

The title compound crystallizes in the non-centrosymmetric space group Pca21; however, in the absence of significant anomalous scattering effects, the Flack parameter is essentially meaningless. Accordingly, Friedel pairs were merged. Hydrogen atoms bound to aromatic carbon atoms were placed in idealized positions with d(C—H) = 0.95 Å and were included in the refinement in the riding model approximation with U(H) set to 1.2 Ueq(C). The hydrogen atoms of the methyl groups were allowed to rotate with a fixed angle around the C–N bond to best fit the experimental electron density, with U(H) set to 1.5 Ueq(C) and d(C—H) = 0.98 Å.

Computing details top

Data collection: APEX2, (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97; molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing 50% probability displacement ellipsoids. All H atoms were omitted for clarity.
1,1,2,2-Tetrakis(dimethylamino)ethane-1,2-diium bis(tetraphenylborate) acetone disolvate top
Crystal data top
C10H24N42+·2C24H20B·2C3H6ODx = 1.167 Mg m3
Mr = 954.91Melting point: 483 K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 9611 reflections
a = 30.0601 (9) Åθ = 1.4–25.1°
b = 9.9321 (3) ŵ = 0.07 mm1
c = 18.2054 (6) ÅT = 100 K
V = 5435.4 (3) Å3Block, yellow
Z = 40.30 × 0.24 × 0.18 mm
F(000) = 2056
Data collection top
Bruker Kappa APEXII DUO
diffractometer
4058 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.054
Graphite monochromatorθmax = 25.1°, θmin = 1.4°
ϕ scans, and ω scansh = 3534
36726 measured reflectionsk = 1111
4983 independent reflectionsl = 2121
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: difference Fourier map
wR(F2) = 0.109H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0601P)2 + 0.9312P]
where P = (Fo2 + 2Fc2)/3
4983 reflections(Δ/σ)max < 0.001
661 parametersΔρmax = 0.39 e Å3
1 restraintΔρmin = 0.30 e Å3
Crystal data top
C10H24N42+·2C24H20B·2C3H6OV = 5435.4 (3) Å3
Mr = 954.91Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 30.0601 (9) ŵ = 0.07 mm1
b = 9.9321 (3) ÅT = 100 K
c = 18.2054 (6) Å0.30 × 0.24 × 0.18 mm
Data collection top
Bruker Kappa APEXII DUO
diffractometer
4058 reflections with I > 2σ(I)
36726 measured reflectionsRint = 0.054
4983 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0461 restraint
wR(F2) = 0.109H-atom parameters constrained
S = 1.05Δρmax = 0.39 e Å3
4983 reflectionsΔρmin = 0.30 e Å3
661 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.12707 (10)0.7168 (4)0.37772 (19)0.0200 (8)
C20.13799 (11)0.7692 (3)0.3027 (2)0.0220 (8)
N10.14503 (9)0.6019 (3)0.39743 (16)0.0233 (7)
C30.16208 (12)0.5055 (4)0.3436 (2)0.0338 (9)
H3A0.15420.53550.29400.051*
H3B0.14890.41680.35280.051*
H3C0.19450.49950.34800.051*
C40.15054 (12)0.5609 (4)0.4744 (2)0.0320 (9)
H4A0.14840.64030.50620.048*
H4B0.17970.51870.48090.048*
H4C0.12720.49650.48760.048*
N20.10013 (9)0.7912 (3)0.41826 (16)0.0228 (7)
C50.09189 (12)0.9346 (4)0.4024 (2)0.0282 (9)
H5A0.11460.96790.36820.042*
H5B0.09330.98640.44820.042*
H5C0.06240.94490.38020.042*
C60.07184 (12)0.7379 (4)0.4777 (2)0.0312 (9)
H6A0.07020.63960.47370.047*
H6B0.04190.77610.47340.047*
H6C0.08460.76250.52530.047*
N30.10484 (9)0.7788 (3)0.25641 (16)0.0232 (7)
C70.10512 (12)0.8684 (4)0.1915 (2)0.0344 (9)
H7A0.12880.93540.19690.052*
H7B0.07640.91430.18750.052*
H7C0.11040.81490.14710.052*
C80.06283 (11)0.7054 (4)0.2677 (2)0.0281 (9)
H8A0.06750.63290.30340.042*
H8B0.05290.66680.22090.042*
H8C0.04010.76750.28630.042*
N40.18007 (9)0.8008 (3)0.28813 (16)0.0232 (7)
C90.21206 (11)0.8266 (4)0.3481 (2)0.0272 (8)
H9A0.19580.84620.39350.041*
H9B0.23080.90390.33530.041*
H9C0.23080.74700.35540.041*
C100.19960 (12)0.7968 (4)0.2144 (2)0.0322 (9)
H10A0.18050.74360.18190.048*
H10B0.22920.75560.21680.048*
H10C0.20220.88870.19520.048*
B10.24717 (12)0.1824 (4)0.4752 (2)0.0188 (8)
C110.23805 (10)0.1708 (3)0.38587 (19)0.0181 (7)
C120.19512 (11)0.1679 (3)0.35475 (19)0.0223 (8)
H12A0.17010.16900.38650.027*
C130.18807 (12)0.1636 (4)0.2796 (2)0.0265 (8)
H13A0.15850.16300.26100.032*
C140.22340 (13)0.1601 (4)0.2316 (2)0.0311 (9)
H14A0.21860.15570.18010.037*
C150.26608 (13)0.1631 (4)0.2598 (2)0.0323 (9)
H15A0.29090.16160.22750.039*
C160.27273 (11)0.1682 (4)0.3351 (2)0.0255 (8)
H16A0.30240.17010.35290.031*
C170.29451 (10)0.1072 (3)0.49522 (19)0.0189 (7)
C180.30372 (11)0.0243 (4)0.4717 (2)0.0243 (8)
H18A0.28180.07050.44380.029*
C190.34317 (11)0.0900 (4)0.4872 (2)0.0287 (9)
H19A0.34770.17960.47050.034*
C200.37621 (11)0.0253 (4)0.5272 (2)0.0287 (9)
H20A0.40360.06900.53730.034*
C210.36841 (11)0.1035 (4)0.5519 (2)0.0278 (9)
H21A0.39050.14870.57990.033*
C220.32844 (11)0.1680 (4)0.53598 (19)0.0227 (8)
H22A0.32400.25700.55360.027*
C230.25020 (10)0.3409 (3)0.50010 (19)0.0188 (7)
C240.26607 (10)0.4427 (3)0.45320 (19)0.0201 (8)
H24A0.27370.42040.40400.024*
C250.27097 (11)0.5748 (4)0.4767 (2)0.0281 (9)
H25A0.28170.64100.44340.034*
C260.26053 (11)0.6112 (4)0.5475 (2)0.0272 (9)
H26A0.26410.70180.56310.033*
C270.24495 (11)0.5157 (3)0.5953 (2)0.0230 (8)
H27A0.23740.53980.64430.028*
C280.24023 (10)0.3832 (3)0.57183 (19)0.0196 (8)
H28A0.22980.31820.60600.024*
C290.20597 (11)0.1089 (3)0.52084 (18)0.0190 (8)
C300.16441 (11)0.1728 (4)0.52823 (19)0.0210 (8)
H30A0.16050.25900.50650.025*
C310.12900 (11)0.1158 (4)0.56579 (19)0.0256 (8)
H31A0.10170.16340.56980.031*
C320.13319 (12)0.0089 (4)0.5972 (2)0.0315 (9)
H32A0.10890.04920.62240.038*
C330.17346 (13)0.0747 (4)0.5914 (2)0.0357 (10)
H33A0.17700.16070.61340.043*
C340.20880 (12)0.0171 (4)0.5539 (2)0.0271 (8)
H34A0.23600.06550.55070.033*
B20.00931 (12)0.3446 (4)0.2005 (2)0.0188 (8)
C350.04912 (11)0.4242 (4)0.15515 (18)0.0194 (7)
C360.09428 (10)0.4095 (3)0.17347 (19)0.0217 (8)
H36A0.10210.35350.21370.026*
C370.12799 (12)0.4743 (4)0.1345 (2)0.0283 (9)
H37A0.15810.46090.14840.034*
C380.11829 (12)0.5568 (4)0.0767 (2)0.0332 (10)
H38A0.14140.60170.05090.040*
C390.07416 (13)0.5741 (5)0.0562 (2)0.0363 (10)
H39A0.06680.63100.01610.044*
C400.04072 (11)0.5075 (4)0.0948 (2)0.0264 (8)
H40A0.01080.51930.07930.032*
C410.03901 (10)0.4195 (3)0.18651 (18)0.0189 (7)
C420.04449 (11)0.5592 (4)0.19129 (19)0.0231 (8)
H42A0.01910.61260.20200.028*
C430.08479 (11)0.6238 (4)0.18133 (19)0.0252 (8)
H43A0.08650.71880.18670.030*
C440.12205 (12)0.5531 (4)0.1640 (2)0.0336 (10)
H44A0.14990.59710.15800.040*
C450.11844 (12)0.4168 (4)0.1554 (2)0.0363 (10)
H45A0.14370.36610.14090.044*
C460.07803 (11)0.3514 (4)0.1677 (2)0.0285 (9)
H46A0.07700.25610.16300.034*
C470.00597 (10)0.1890 (4)0.17045 (19)0.0205 (8)
C480.00876 (11)0.0813 (4)0.2141 (2)0.0240 (8)
H48A0.01420.09710.26480.029*
C490.01574 (11)0.0472 (4)0.1867 (2)0.0285 (9)
H49A0.02590.11640.21850.034*
C500.00809 (11)0.0752 (4)0.1140 (2)0.0271 (9)
H50A0.01280.16330.09530.032*
C510.00657 (11)0.0272 (4)0.0681 (2)0.0274 (9)
H51A0.01180.00990.01760.033*
C520.01353 (11)0.1557 (4)0.0967 (2)0.0235 (8)
H52A0.02390.22420.06450.028*
C530.02121 (10)0.3463 (3)0.28940 (19)0.0187 (7)
C540.00099 (10)0.4337 (4)0.33938 (19)0.0209 (7)
H54A0.02180.49190.32200.025*
C550.01254 (11)0.4395 (4)0.41325 (19)0.0262 (8)
H55A0.00230.50070.44500.031*
C560.04521 (12)0.3573 (4)0.4405 (2)0.0279 (9)
H56A0.05350.36170.49080.033*
C570.06587 (11)0.2681 (4)0.3933 (2)0.0267 (9)
H57A0.08860.21040.41130.032*
C580.05373 (11)0.2622 (4)0.3203 (2)0.0239 (8)
H58A0.06800.19820.28960.029*
O10.29178 (12)0.6328 (4)0.2820 (2)0.0693 (11)
C590.32840 (16)0.6770 (6)0.3005 (3)0.0565 (14)
C600.36004 (18)0.5888 (8)0.3382 (3)0.086 (2)
H60A0.36810.62850.38570.129*
H60B0.38680.57840.30800.129*
H60C0.34640.50040.34620.129*
C610.3405 (2)0.8204 (6)0.2871 (3)0.0740 (17)
H61A0.31740.86310.25700.111*
H61B0.36900.82460.26130.111*
H61C0.34290.86780.33410.111*
O20.47849 (12)0.1730 (5)0.3833 (2)0.0902 (15)
C620.43772 (18)0.1911 (7)0.3802 (3)0.0662 (17)
C630.40778 (16)0.0963 (7)0.3460 (3)0.0734 (17)
H63A0.39380.13820.30300.110*
H63B0.38470.06990.38120.110*
H63C0.42450.01640.33050.110*
C640.4158 (2)0.3130 (7)0.4088 (4)0.095 (2)
H64A0.43590.35940.44280.142*
H64B0.38850.28750.43480.142*
H64C0.40830.37310.36790.142*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0152 (16)0.0201 (19)0.0246 (19)0.0010 (14)0.0072 (14)0.0050 (16)
C20.0197 (18)0.0111 (18)0.035 (2)0.0040 (14)0.0055 (16)0.0089 (16)
N10.0204 (14)0.0149 (16)0.0347 (17)0.0001 (12)0.0083 (13)0.0015 (13)
C30.030 (2)0.016 (2)0.055 (3)0.0080 (16)0.0070 (19)0.0104 (19)
C40.027 (2)0.026 (2)0.043 (2)0.0009 (16)0.0094 (17)0.0097 (19)
N20.0216 (15)0.0168 (16)0.0300 (16)0.0025 (13)0.0047 (13)0.0031 (13)
C50.035 (2)0.019 (2)0.031 (2)0.0076 (16)0.0051 (16)0.0051 (17)
C60.0277 (19)0.031 (2)0.035 (2)0.0048 (16)0.0025 (17)0.0003 (19)
N30.0193 (14)0.0223 (16)0.0282 (16)0.0001 (12)0.0036 (13)0.0049 (14)
C70.032 (2)0.042 (3)0.029 (2)0.0001 (18)0.0065 (17)0.0055 (19)
C80.0207 (18)0.028 (2)0.035 (2)0.0031 (16)0.0084 (16)0.0093 (18)
N40.0199 (15)0.0192 (17)0.0306 (16)0.0010 (12)0.0024 (13)0.0073 (13)
C90.0206 (18)0.022 (2)0.039 (2)0.0028 (15)0.0083 (16)0.0030 (17)
C100.027 (2)0.034 (2)0.035 (2)0.0010 (17)0.0041 (17)0.0056 (19)
B10.0169 (18)0.015 (2)0.025 (2)0.0009 (15)0.0046 (16)0.0021 (17)
C110.0207 (17)0.0089 (17)0.0248 (18)0.0004 (13)0.0012 (15)0.0002 (14)
C120.0196 (17)0.0193 (19)0.028 (2)0.0002 (14)0.0004 (15)0.0022 (16)
C130.0265 (19)0.020 (2)0.033 (2)0.0016 (16)0.0108 (16)0.0010 (17)
C140.038 (2)0.033 (2)0.022 (2)0.0005 (18)0.0036 (17)0.0027 (18)
C150.030 (2)0.037 (2)0.029 (2)0.0027 (17)0.0039 (17)0.0041 (19)
C160.0194 (18)0.029 (2)0.028 (2)0.0006 (15)0.0003 (15)0.0033 (17)
C170.0150 (16)0.0188 (19)0.0228 (18)0.0033 (14)0.0021 (14)0.0038 (15)
C180.0214 (18)0.023 (2)0.029 (2)0.0013 (15)0.0052 (15)0.0000 (16)
C190.0245 (19)0.023 (2)0.039 (2)0.0040 (16)0.0009 (17)0.0036 (18)
C200.022 (2)0.030 (2)0.034 (2)0.0072 (16)0.0030 (16)0.0051 (18)
C210.0188 (18)0.033 (2)0.031 (2)0.0051 (16)0.0072 (16)0.0042 (18)
C220.0207 (18)0.022 (2)0.0257 (19)0.0035 (15)0.0010 (15)0.0006 (16)
C230.0118 (15)0.0173 (18)0.0272 (18)0.0028 (14)0.0069 (14)0.0038 (16)
C240.0147 (16)0.0180 (19)0.028 (2)0.0034 (14)0.0068 (13)0.0028 (16)
C250.0209 (18)0.021 (2)0.042 (2)0.0023 (15)0.0081 (16)0.0098 (18)
C260.0218 (18)0.0142 (18)0.046 (3)0.0010 (14)0.0131 (17)0.0070 (18)
C270.0212 (18)0.0185 (19)0.0293 (19)0.0016 (15)0.0065 (15)0.0038 (16)
C280.0117 (16)0.0196 (19)0.0277 (19)0.0009 (13)0.0026 (14)0.0016 (16)
C290.0208 (18)0.0161 (19)0.0202 (18)0.0021 (14)0.0028 (14)0.0038 (15)
C300.0229 (19)0.0172 (19)0.0229 (18)0.0027 (15)0.0007 (14)0.0014 (15)
C310.0224 (18)0.028 (2)0.0259 (19)0.0045 (16)0.0031 (15)0.0077 (17)
C320.028 (2)0.031 (2)0.036 (2)0.0136 (17)0.0097 (17)0.0019 (19)
C330.046 (2)0.021 (2)0.040 (2)0.0070 (18)0.0094 (19)0.0089 (19)
C340.029 (2)0.021 (2)0.031 (2)0.0016 (16)0.0005 (16)0.0029 (17)
B20.0157 (18)0.020 (2)0.021 (2)0.0021 (16)0.0029 (15)0.0019 (17)
C350.0190 (17)0.0212 (19)0.0180 (17)0.0014 (15)0.0011 (13)0.0094 (15)
C360.0212 (17)0.0169 (19)0.027 (2)0.0006 (14)0.0012 (15)0.0050 (15)
C370.0192 (19)0.026 (2)0.040 (2)0.0065 (16)0.0032 (16)0.0138 (18)
C380.029 (2)0.042 (2)0.028 (2)0.0171 (18)0.0109 (17)0.0096 (19)
C390.040 (2)0.047 (3)0.022 (2)0.0151 (19)0.0016 (17)0.0033 (19)
C400.0188 (18)0.038 (2)0.0225 (18)0.0091 (16)0.0015 (15)0.0025 (17)
C410.0207 (17)0.0210 (19)0.0150 (16)0.0036 (14)0.0010 (13)0.0012 (15)
C420.0203 (18)0.023 (2)0.0265 (19)0.0036 (15)0.0049 (15)0.0061 (16)
C430.0261 (19)0.024 (2)0.0257 (19)0.0008 (15)0.0039 (16)0.0013 (16)
C440.0225 (19)0.032 (2)0.046 (2)0.0067 (17)0.0054 (17)0.015 (2)
C450.0199 (19)0.035 (3)0.054 (3)0.0042 (17)0.0044 (18)0.010 (2)
C460.0205 (18)0.021 (2)0.044 (2)0.0026 (15)0.0015 (16)0.0107 (18)
C470.0119 (15)0.025 (2)0.024 (2)0.0004 (14)0.0023 (14)0.0018 (16)
C480.0212 (18)0.022 (2)0.029 (2)0.0005 (15)0.0018 (16)0.0002 (17)
C490.0270 (19)0.019 (2)0.039 (2)0.0025 (15)0.0063 (17)0.0016 (18)
C500.0185 (17)0.017 (2)0.045 (2)0.0021 (15)0.0103 (16)0.0091 (18)
C510.0159 (18)0.029 (2)0.038 (2)0.0014 (15)0.0042 (16)0.0105 (19)
C520.0161 (17)0.024 (2)0.030 (2)0.0013 (14)0.0001 (15)0.0029 (17)
C530.0160 (16)0.0173 (18)0.0229 (18)0.0059 (14)0.0033 (14)0.0005 (15)
C540.0182 (17)0.0240 (19)0.0204 (17)0.0016 (14)0.0008 (14)0.0010 (16)
C550.0270 (19)0.030 (2)0.0218 (19)0.0001 (16)0.0038 (15)0.0010 (17)
C560.033 (2)0.032 (2)0.0187 (18)0.0072 (17)0.0076 (16)0.0045 (17)
C570.0240 (19)0.026 (2)0.030 (2)0.0032 (16)0.0096 (16)0.0062 (18)
C580.0220 (18)0.0193 (19)0.031 (2)0.0014 (15)0.0002 (15)0.0001 (16)
O10.051 (2)0.088 (3)0.069 (2)0.011 (2)0.0060 (18)0.008 (2)
C590.043 (3)0.081 (4)0.046 (3)0.010 (3)0.003 (2)0.003 (3)
C600.067 (4)0.141 (6)0.050 (3)0.032 (4)0.008 (3)0.015 (4)
C610.082 (4)0.082 (4)0.059 (3)0.010 (3)0.008 (3)0.022 (3)
O20.046 (2)0.165 (5)0.060 (2)0.028 (2)0.0040 (19)0.018 (3)
C620.053 (3)0.109 (5)0.037 (3)0.025 (3)0.012 (2)0.011 (3)
C630.047 (3)0.112 (5)0.061 (3)0.023 (3)0.018 (3)0.006 (4)
C640.073 (4)0.105 (6)0.106 (6)0.026 (4)0.031 (4)0.000 (5)
Geometric parameters (Å, º) top
C1—N11.313 (4)C30—C311.386 (5)
C1—N21.321 (4)C30—H30A0.9500
C1—C21.498 (5)C31—C321.370 (5)
C2—N31.309 (4)C31—H31A0.9500
C2—N41.330 (4)C32—C331.380 (6)
N1—C31.463 (5)C32—H32A0.9500
N1—C41.469 (5)C33—C341.386 (5)
C3—H3A0.9800C33—H33A0.9500
C3—H3B0.9800C34—H34A0.9500
C3—H3C0.9800B2—C471.642 (5)
C4—H4A0.9800B2—C411.652 (5)
C4—H4B0.9800B2—C351.655 (5)
C4—H4C0.9800B2—C531.658 (5)
N2—C61.474 (5)C35—C401.399 (5)
N2—C51.475 (5)C35—C361.405 (5)
C5—H5A0.9800C36—C371.394 (5)
C5—H5B0.9800C36—H36A0.9500
C5—H5C0.9800C37—C381.365 (6)
C6—H6A0.9800C37—H37A0.9500
C6—H6B0.9800C38—C391.389 (5)
C6—H6C0.9800C38—H38A0.9500
N3—C81.473 (4)C39—C401.393 (5)
N3—C71.479 (5)C39—H39A0.9500
C7—H7A0.9800C40—H40A0.9500
C7—H7B0.9800C41—C461.397 (5)
C7—H7C0.9800C41—C421.400 (5)
C8—H8A0.9800C42—C431.383 (5)
C8—H8B0.9800C42—H42A0.9500
C8—H8C0.9800C43—C441.360 (5)
N4—C101.465 (5)C43—H43A0.9500
N4—C91.478 (4)C44—C451.366 (5)
C9—H9A0.9800C44—H44A0.9500
C9—H9B0.9800C45—C461.396 (5)
C9—H9C0.9800C45—H45A0.9500
C10—H10A0.9800C46—H46A0.9500
C10—H10B0.9800C47—C521.401 (5)
C10—H10C0.9800C47—C481.405 (5)
B1—C231.641 (5)C48—C491.386 (5)
B1—C171.648 (5)C48—H48A0.9500
B1—C111.654 (5)C49—C501.372 (6)
B1—C291.660 (5)C49—H49A0.9500
C11—C161.394 (5)C50—C511.387 (5)
C11—C121.410 (5)C50—H50A0.9500
C12—C131.385 (5)C51—C521.394 (5)
C12—H12A0.9500C51—H51A0.9500
C13—C141.376 (5)C52—H52A0.9500
C13—H13A0.9500C53—C541.397 (5)
C14—C151.382 (5)C53—C581.404 (5)
C14—H14A0.9500C54—C551.390 (5)
C15—C161.385 (5)C54—H54A0.9500
C15—H15A0.9500C55—C561.370 (5)
C16—H16A0.9500C55—H55A0.9500
C17—C221.398 (5)C56—C571.381 (5)
C17—C181.402 (5)C56—H56A0.9500
C18—C191.383 (5)C57—C581.379 (5)
C18—H18A0.9500C57—H57A0.9500
C19—C201.389 (5)C58—H58A0.9500
C19—H19A0.9500O1—C591.232 (6)
C20—C211.375 (5)C59—C601.464 (7)
C20—H20A0.9500C59—C611.490 (8)
C21—C221.392 (5)C60—H60A0.9800
C21—H21A0.9500C60—H60B0.9800
C22—H22A0.9500C60—H60C0.9800
C23—C281.404 (5)C61—H61A0.9800
C23—C241.407 (5)C61—H61B0.9800
C24—C251.388 (5)C61—H61C0.9800
C24—H24A0.9500O2—C621.240 (6)
C25—C261.374 (6)C62—C631.444 (8)
C25—H25A0.9500C62—C641.474 (8)
C26—C271.371 (5)C63—H63A0.9800
C26—H26A0.9500C63—H63B0.9800
C27—C281.391 (5)C63—H63C0.9800
C27—H27A0.9500C64—H64A0.9800
C28—H28A0.9500C64—H64B0.9800
C29—C341.391 (5)C64—H64C0.9800
C29—C301.408 (5)
N1—C1—N2125.8 (3)C34—C29—C30114.7 (3)
N1—C1—C2117.5 (3)C34—C29—B1124.5 (3)
N2—C1—C2116.7 (3)C30—C29—B1120.7 (3)
N3—C2—N4125.3 (3)C31—C30—C29123.0 (3)
N3—C2—C1116.5 (3)C31—C30—H30A118.5
N4—C2—C1118.2 (3)C29—C30—H30A118.5
C1—N1—C3122.0 (3)C32—C31—C30120.3 (3)
C1—N1—C4123.2 (3)C32—C31—H31A119.8
C3—N1—C4114.7 (3)C30—C31—H31A119.8
N1—C3—H3A109.5C31—C32—C33118.5 (3)
N1—C3—H3B109.5C31—C32—H32A120.8
H3A—C3—H3B109.5C33—C32—H32A120.8
N1—C3—H3C109.5C32—C33—C34121.0 (4)
H3A—C3—H3C109.5C32—C33—H33A119.5
H3B—C3—H3C109.5C34—C33—H33A119.5
N1—C4—H4A109.5C33—C34—C29122.5 (3)
N1—C4—H4B109.5C33—C34—H34A118.7
H4A—C4—H4B109.5C29—C34—H34A118.7
N1—C4—H4C109.5C47—B2—C41108.6 (3)
H4A—C4—H4C109.5C47—B2—C35109.1 (3)
H4B—C4—H4C109.5C41—B2—C35110.1 (3)
C1—N2—C6124.2 (3)C47—B2—C53110.4 (3)
C1—N2—C5122.2 (3)C41—B2—C53109.6 (3)
C6—N2—C5113.2 (3)C35—B2—C53109.0 (3)
N2—C5—H5A109.5C40—C35—C36115.0 (3)
N2—C5—H5B109.5C40—C35—B2123.0 (3)
H5A—C5—H5B109.5C36—C35—B2122.0 (3)
N2—C5—H5C109.5C37—C36—C35122.2 (3)
H5A—C5—H5C109.5C37—C36—H36A118.9
H5B—C5—H5C109.5C35—C36—H36A118.9
N2—C6—H6A109.5C38—C37—C36120.9 (3)
N2—C6—H6B109.5C38—C37—H37A119.5
H6A—C6—H6B109.5C36—C37—H37A119.5
N2—C6—H6C109.5C37—C38—C39119.0 (3)
H6A—C6—H6C109.5C37—C38—H38A120.5
H6B—C6—H6C109.5C39—C38—H38A120.5
C2—N3—C8121.8 (3)C38—C39—C40119.7 (4)
C2—N3—C7123.6 (3)C38—C39—H39A120.2
C8—N3—C7114.5 (3)C40—C39—H39A120.2
N3—C7—H7A109.5C39—C40—C35123.1 (3)
N3—C7—H7B109.5C39—C40—H40A118.4
H7A—C7—H7B109.5C35—C40—H40A118.4
N3—C7—H7C109.5C46—C41—C42113.4 (3)
H7A—C7—H7C109.5C46—C41—B2123.9 (3)
H7B—C7—H7C109.5C42—C41—B2122.7 (3)
N3—C8—H8A109.5C43—C42—C41123.7 (3)
N3—C8—H8B109.5C43—C42—H42A118.1
H8A—C8—H8B109.5C41—C42—H42A118.1
N3—C8—H8C109.5C44—C43—C42120.8 (4)
H8A—C8—H8C109.5C44—C43—H43A119.6
H8B—C8—H8C109.5C42—C43—H43A119.6
C2—N4—C10123.9 (3)C43—C44—C45118.2 (4)
C2—N4—C9120.8 (3)C43—C44—H44A120.9
C10—N4—C9114.9 (3)C45—C44—H44A120.9
N4—C9—H9A109.5C44—C45—C46120.8 (4)
N4—C9—H9B109.5C44—C45—H45A119.6
H9A—C9—H9B109.5C46—C45—H45A119.6
N4—C9—H9C109.5C45—C46—C41123.0 (3)
H9A—C9—H9C109.5C45—C46—H46A118.5
H9B—C9—H9C109.5C41—C46—H46A118.5
N4—C10—H10A109.5C52—C47—C48114.4 (3)
N4—C10—H10B109.5C52—C47—B2122.1 (3)
H10A—C10—H10B109.5C48—C47—B2123.2 (3)
N4—C10—H10C109.5C49—C48—C47123.0 (3)
H10A—C10—H10C109.5C49—C48—H48A118.5
H10B—C10—H10C109.5C47—C48—H48A118.5
C23—B1—C17109.0 (3)C50—C49—C48120.6 (4)
C23—B1—C11110.3 (3)C50—C49—H49A119.7
C17—B1—C11109.2 (3)C48—C49—H49A119.7
C23—B1—C29109.0 (3)C49—C50—C51119.0 (3)
C17—B1—C29109.5 (3)C49—C50—H50A120.5
C11—B1—C29109.7 (3)C51—C50—H50A120.5
C16—C11—C12114.7 (3)C50—C51—C52119.6 (4)
C16—C11—B1122.0 (3)C50—C51—H51A120.2
C12—C11—B1123.3 (3)C52—C51—H51A120.2
C13—C12—C11122.5 (3)C51—C52—C47123.3 (4)
C13—C12—H12A118.7C51—C52—H52A118.3
C11—C12—H12A118.7C47—C52—H52A118.3
C14—C13—C12120.7 (3)C54—C53—C58114.3 (3)
C14—C13—H13A119.7C54—C53—B2123.3 (3)
C12—C13—H13A119.7C58—C53—B2122.4 (3)
C13—C14—C15118.7 (3)C55—C54—C53123.2 (3)
C13—C14—H14A120.7C55—C54—H54A118.4
C15—C14—H14A120.7C53—C54—H54A118.4
C14—C15—C16120.2 (3)C56—C55—C54120.3 (3)
C14—C15—H15A119.9C56—C55—H55A119.9
C16—C15—H15A119.9C54—C55—H55A119.9
C15—C16—C11123.3 (3)C55—C56—C57118.7 (3)
C15—C16—H16A118.4C55—C56—H56A120.7
C11—C16—H16A118.4C57—C56—H56A120.7
C22—C17—C18114.8 (3)C58—C57—C56120.5 (3)
C22—C17—B1123.5 (3)C58—C57—H57A119.8
C18—C17—B1121.7 (3)C56—C57—H57A119.8
C19—C18—C17123.1 (3)C57—C58—C53123.0 (3)
C19—C18—H18A118.4C57—C58—H58A118.5
C17—C18—H18A118.4C53—C58—H58A118.5
C18—C19—C20120.1 (4)O1—C59—C60119.7 (6)
C18—C19—H19A119.9O1—C59—C61120.8 (5)
C20—C19—H19A119.9C60—C59—C61119.4 (5)
C21—C20—C19118.6 (3)C59—C60—H60A109.5
C21—C20—H20A120.7C59—C60—H60B109.5
C19—C20—H20A120.7H60A—C60—H60B109.5
C20—C21—C22120.5 (3)C59—C60—H60C109.5
C20—C21—H21A119.8H60A—C60—H60C109.5
C22—C21—H21A119.8H60B—C60—H60C109.5
C21—C22—C17122.8 (3)C59—C61—H61A109.5
C21—C22—H22A118.6C59—C61—H61B109.5
C17—C22—H22A118.6H61A—C61—H61B109.5
C28—C23—C24114.9 (3)C59—C61—H61C109.5
C28—C23—B1122.1 (3)H61A—C61—H61C109.5
C24—C23—B1122.8 (3)H61B—C61—H61C109.5
C25—C24—C23121.9 (3)O2—C62—C63122.8 (6)
C25—C24—H24A119.0O2—C62—C64123.0 (6)
C23—C24—H24A119.0C63—C62—C64114.2 (5)
C26—C25—C24120.9 (3)C62—C63—H63A109.5
C26—C25—H25A119.6C62—C63—H63B109.5
C24—C25—H25A119.6H63A—C63—H63B109.5
C27—C26—C25119.5 (3)C62—C63—H63C109.5
C27—C26—H26A120.3H63A—C63—H63C109.5
C25—C26—H26A120.3H63B—C63—H63C109.5
C26—C27—C28119.6 (3)C62—C64—H64A109.5
C26—C27—H27A120.2C62—C64—H64B109.5
C28—C27—H27A120.2H64A—C64—H64B109.5
C27—C28—C23123.2 (3)C62—C64—H64C109.5
C27—C28—H28A118.4H64A—C64—H64C109.5
C23—C28—H28A118.4H64B—C64—H64C109.5
N1—C1—C2—N3115.9 (3)C17—B1—C29—C30164.0 (3)
N2—C1—C2—N364.2 (4)C11—B1—C29—C3076.1 (4)
N1—C1—C2—N463.4 (4)C34—C29—C30—C310.3 (5)
N2—C1—C2—N4116.4 (3)B1—C29—C30—C31179.9 (3)
N2—C1—N1—C3159.6 (3)C29—C30—C31—C320.7 (5)
C2—C1—N1—C320.5 (4)C30—C31—C32—C330.9 (5)
N2—C1—N1—C421.7 (5)C31—C32—C33—C340.8 (6)
C2—C1—N1—C4158.1 (3)C32—C33—C34—C290.4 (6)
N1—C1—N2—C625.5 (5)C30—C29—C34—C330.2 (5)
C2—C1—N2—C6154.6 (3)B1—C29—C34—C33179.9 (4)
N1—C1—N2—C5161.5 (3)C47—B2—C35—C4097.6 (4)
C2—C1—N2—C518.3 (4)C41—B2—C35—C4021.4 (4)
N4—C2—N3—C8160.9 (3)C53—B2—C35—C40141.7 (3)
C1—C2—N3—C818.3 (5)C47—B2—C35—C3680.4 (4)
N4—C2—N3—C722.6 (5)C41—B2—C35—C36160.5 (3)
C1—C2—N3—C7158.1 (3)C53—B2—C35—C3640.2 (4)
N3—C2—N4—C1026.6 (5)C40—C35—C36—C370.5 (5)
C1—C2—N4—C10152.7 (3)B2—C35—C36—C37178.7 (3)
N3—C2—N4—C9161.1 (3)C35—C36—C37—C380.6 (5)
C1—C2—N4—C919.7 (5)C36—C37—C38—C391.0 (6)
C23—B1—C11—C1688.2 (4)C37—C38—C39—C400.1 (6)
C17—B1—C11—C1631.6 (4)C38—C39—C40—C351.2 (6)
C29—B1—C11—C16151.7 (3)C36—C35—C40—C391.4 (5)
C23—B1—C11—C1289.3 (4)B2—C35—C40—C39179.6 (3)
C17—B1—C11—C12150.9 (3)C47—B2—C41—C4612.9 (5)
C29—B1—C11—C1230.8 (4)C35—B2—C41—C46132.3 (3)
C16—C11—C12—C130.3 (5)C53—B2—C41—C46107.8 (4)
B1—C11—C12—C13177.3 (3)C47—B2—C41—C42166.0 (3)
C11—C12—C13—C140.9 (6)C35—B2—C41—C4246.6 (4)
C12—C13—C14—C151.0 (6)C53—B2—C41—C4273.4 (4)
C13—C14—C15—C160.6 (6)C46—C41—C42—C432.5 (5)
C14—C15—C16—C110.1 (6)B2—C41—C42—C43178.6 (3)
C12—C11—C16—C150.1 (5)C41—C42—C43—C441.8 (6)
B1—C11—C16—C15177.8 (3)C42—C43—C44—C451.1 (6)
C23—B1—C17—C228.0 (5)C43—C44—C45—C463.1 (6)
C11—B1—C17—C22128.6 (3)C44—C45—C46—C412.4 (6)
C29—B1—C17—C22111.2 (3)C42—C41—C46—C450.4 (5)
C23—B1—C17—C18171.7 (3)B2—C41—C46—C45179.4 (3)
C11—B1—C17—C1851.0 (4)C41—B2—C47—C5285.1 (4)
C29—B1—C17—C1869.1 (4)C35—B2—C47—C5234.9 (4)
C22—C17—C18—C190.0 (5)C53—B2—C47—C52154.7 (3)
B1—C17—C18—C19179.7 (3)C41—B2—C47—C4888.5 (4)
C17—C18—C19—C200.7 (6)C35—B2—C47—C48151.5 (3)
C18—C19—C20—C211.2 (6)C53—B2—C47—C4831.7 (4)
C19—C20—C21—C221.0 (5)C52—C47—C48—C490.7 (5)
C20—C21—C22—C170.2 (5)B2—C47—C48—C49173.4 (3)
C18—C17—C22—C210.3 (5)C47—C48—C49—C500.4 (5)
B1—C17—C22—C21179.4 (3)C48—C49—C50—C510.3 (5)
C17—B1—C23—C2885.8 (4)C49—C50—C51—C520.5 (5)
C11—B1—C23—C28154.3 (3)C50—C51—C52—C470.8 (5)
C29—B1—C23—C2833.7 (4)C48—C47—C52—C510.8 (5)
C17—B1—C23—C2489.3 (4)B2—C47—C52—C51173.3 (3)
C11—B1—C23—C2430.6 (4)C47—B2—C53—C54138.2 (3)
C29—B1—C23—C24151.2 (3)C41—B2—C53—C5418.6 (4)
C28—C23—C24—C250.5 (5)C35—B2—C53—C54102.0 (3)
B1—C23—C24—C25175.9 (3)C47—B2—C53—C5843.9 (4)
C23—C24—C25—C260.2 (5)C41—B2—C53—C58163.5 (3)
C24—C25—C26—C270.2 (5)C35—B2—C53—C5875.9 (4)
C25—C26—C27—C280.5 (5)C58—C53—C54—C551.3 (5)
C26—C27—C28—C230.8 (5)B2—C53—C54—C55176.8 (3)
C24—C23—C28—C270.8 (5)C53—C54—C55—C560.1 (6)
B1—C23—C28—C27176.3 (3)C54—C55—C56—C570.8 (5)
C23—B1—C29—C34135.5 (3)C55—C56—C57—C580.0 (5)
C17—B1—C29—C3416.3 (5)C56—C57—C58—C531.5 (5)
C11—B1—C29—C34103.6 (4)C54—C53—C58—C572.1 (5)
C23—B1—C29—C3044.8 (4)B2—C53—C58—C57176.0 (3)

Experimental details

Crystal data
Chemical formulaC10H24N42+·2C24H20B·2C3H6O
Mr954.91
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)100
a, b, c (Å)30.0601 (9), 9.9321 (3), 18.2054 (6)
V3)5435.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.30 × 0.24 × 0.18
Data collection
DiffractometerBruker Kappa APEXII DUO
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
36726, 4983, 4058
Rint0.054
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.109, 1.05
No. of reflections4983
No. of parameters661
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.30

Computer programs: APEX2, (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97, DIAMOND (Brandenburg & Putz, 2005).

 

Acknowledgements

The authors thank Dr Wolfgang Frey (Institut für Organische Chemie, Universität Stuttgart) for the measuring of the crystal data.

References

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Volume 68| Part 5| May 2012| Page o1371
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