Ζ. Kristallogr. NCS 215 (2000) 301-302 301
© by Oldenbourg Wissenschaftsverlag, München
Crystal structure of l,3-dimethyl-2-[l-methyl-l-(3-methyl-l-triazeno)- ethyl]benzimidazolium hexafluorophosphate,
[C 7 H4N2(CH3)2C(CH3)2N3HCH3] + [PF 6 ]-
K. P e t e r s * ' E . - M . Peters
1, M. Ach" and H. Quast
11I Max-Planck-Institut für Festkörperforschung, Heisenbergstraße 1, D-70506 Stuttgart, Germany
II Universität Würzburg, Institut für Organische Chemie, Am Hubland, D-97074 Würzburg, Germany Received October 4, 1999, CCDC-No. 1267/303
Table 1. Data collection and handling.
C22
Acstract
C 1 3 H 2 0 N 5 P F 6 ,
monoclinic,
P\2\/a\(No. 14),
a= 13.374(3) Ä, Zj = 13.898(4) Ä,c = 9.377(2) Ä, β = 95.20(2)°, V= 1735.7 Ä
3, Z = 4, R
gt(F) = 0.058, wR(F) = 0.058, T = 293 K.
Source of material
The title compound was prepared in 86% yield, according to [1]
by slow addition of a solution of acetic acid (2 equiv.) and ammo- nium hexafluorophosphate (1.1 equiv.) in ethanol/water (5:1) to a cooled solution of the [3+2] cycloadduct of methyl azide to 1,3-dimethyl-2-( 1 -methylethylidene)-2,3-dihydro- lH-benz- imidazole [3]. Recrystallization of the product from methanol at 253 Κ afforded colourless prisms, mp 448 Κ - 451 Κ with decomposition.
Crystal: colourless prism, size 0.5 χ 0.55 χ 0.3 mm Wavelength: Mo Ka radiation (0.71073 Ä)
μ: 2.30 cm1
Diffractometer, scan mode: Siemens R3m/V, Wyckoff 55°
W^OmMsurctt, N(hkl)uniqut· 4314,3982
Criterion for Fobs, N(hkl)gt: Fobs > 3 a(Fobs), 3103
N(param),c fired: 244
Program: SHELXTL-plus [4]
Table 2. Atomic coordinates and displacement parameters (in Ä2).
Atom Site X y ζ Ciso
H(5A) 4e 0.0595(2) 0.4876(3) 0.8600(3) 0.08 H(6A) 4e 0.0194(3) 0.6444(3) 0.7913(4) 0.08 H(7A) 4e 0.1004(3) 0.6724(2) 0.6304(4) 0.08 H(8A) 4e 0.1800(2) 0.5444(2) 0.5240(3) 0.08 H(10A) 4e 0.2312(2) 0.2761(2) 0.4691(3) 0.08 H(10B) 4e 0.2779(2) 0.3736(2) 0.5270(3) 0.08 H(10C) 4e 0.1908(2) 0.3739(2) 0.4032(3) 0.08 H(21A) 4e 0.0380(3) 0.1049(3) 0.8008(4) 0.08 H(21B) 4e 0.0525(3) 0.0441(3) 0.6634(4) 0.08 H(21C) 4e 0.0274(3) 0.1268(3) 0.6573(4) 0.08 H(22A) 4e 0.2192(3) 0.1687(2) 0.8213(4) 0.08 H(22B) 4e 0.2694(3) 0.1887(2) 0.6795(4) 0.08 H(22C) 4e 0.2312(3) 0.0851(2) 0.7121(4) 0.08 H(25) 4e 0.017(3) 0.154(2) 0.235(4) 0.08 H(26A) 4e 0.1865(3) 0.1270(3) 0.2553(4) 0.08 H(26B) 4e 0.1133(3) 0.1232(3) 0.1151(4) 0.08 H(26C) 4e 0.1150(3) 0.0386(3) 0.2258(4) 0.08 H(30A) 4e 0.0367(3) 0.2144(3) 0.8409(3) 0.08 H(30B) 4e 0.0870(3) 0.3153(3) 0.8563(3) 0.08 H(30C) 4e 0.0123(3) 0.2898(3) 0.9504(3) 0.08
Table 3. Atomic coordinates and displacement parameters (in Ä2).
Atom Site X y ζ Uu U22 U33 t/ 1 2 U13 U23
N(l) 4e 0.1400(2) 0.3509(2) 0.5900(2) 0.046(1) 0.053(1) 0.043(1) 0.001(1) 0.008(1) 0.001(1) C(2) 4e 0.0943(2) 0.2816(2) 0.6602(3) 0.046(1) 0.057(2) 0.040(1) 0.007(1) 0.001(1) 0.002(1) N(3) 4e 0.0320(2) 0.3247(2) 0.7455(2) 0.043(1) 0.065(2) 0.044(1) 0.005(1) 0.006(1) 0.005(1) C(4) 4e 0.0375(2) 0.4238(2) 0.7303(3) 0.043(1) 0.064(2) 0.043(1) 0.000(1) 0.000(1) 0.001(1) C(5) 4e 0.0112(2) 0.4990(3) 0.7922(3) 0.055(2) 0.086(2) 0.053(2) 0.010(2) 0.007(1) 0.009(2)
* Correspondence author
(e-mail: karpet@vsibml.mpi-stuttgart.mpg.de)
302
[ C 7 H4N 2 ( C H 3 ) 2 C ( C H 3 ) 2 C H 4 N 3]+[ P F6] -Table 3. Continued.
Atom Site X ζ t / l l t/22 i/33 Ul2 Un i/23
C(6) 4e 0.0133(3) 0.5904(3) 0.7516(4) 0.078(2) 0.068(2) 0.072(2) 0.019(2) 0.001(2) 0.015(2)
C(7) 4e 0.0843(3) 0.6074(2) 0.6541(4) 0.080(2) 0.054(2) 0.076(2) 0.003(2) 0.005(2) 0.001(2)
C(8) 4e 0.1318(2) 0.5329(2) 0.5920(3) 0.064(2) 0.060(2) 0.059(2) 0.001(2) 0.006(1) 0.003(1)
C(9) 4e 0.1070(2) 0.4406(2) 0.6311(3) 0.045(2) 0.055(2) 0.044(1) 0.000(1) 0.001(1) 0.001(1)
C(10) 4e 0.2171(2) 0.3422(2) 0.4896(3) 0.060(2) 0.070(2) 0.065(2) 0.000(2) 0.027(2) 0.002(2)
C(20) 4e 0.1156(2) 0.1749(2) 0.6435(3) 0.063(2) 0.054(2) 0.052(2) 0.005(1) 0.000(1) 0.003(1)
C(21) 4e 0.0376(3) 0.1069(3) 0.6985(4) 0.110(3) 0.066(2) 0.080(2) 0.022(2) 0.013(2) 0.008(2)
C(22) 4e 0.2184(3) 0.1526(2) 0.7217(4) 0.083(2) 0.066(2) 0.062(2) 0.012(2) 0.013(2) 0.001(2)
N(23) 4e 0.1233(2) 0.1528(2) 0.4886(3) 0.058(1) 0.054(1) 0.056(1) 0.001(1) 0.008(1) 0.003(1)
N(24) 4e 0.0409(2) 0.1684(2) 0.4195(3) 0.066(2) 0.060(2) 0.061(2) 0.002(1) 0.009(1) 0.004(1)
N(25) 4e 0.0396(2) 0.1495(2) 0.2797(3) 0.076(2) 0.075(2) 0.063(2) 0.007(2) 0.018(1) 0.016(1)
C(26) 4e 0.1214(3) 0.1069(3) 0.2150(4) 0.101(3) 0.087(3) 0.065(2) 0.008(2) 0.003(2) 0.019(2)
C(30) 4e 0.0243(3) 0.2816(3) 0.8582(3) 0.059(2) 0.093(2) 0.057(2) 0.011(2) 0.018(2) 0.009(2)
P ( l ) 4e 0.21852(6) 0.88168(6) 0.96127(8) 0.0472(4) 0.0703(5) 0.0533(4) 0.0008(4) 0.0061(3) 0.0096(4) F ( l ) 4e 0.2262(2) 0.8641(2) 1.1285(2) 0.107(2) 0.119(2) 0.058(1) 0.026(1) 0.015(1) 0.023(1)
F(2) 4e 0.2074(2) 0.9003(2) 0.7941(2) 0.129(2) 0.141(2) 0.052(1) 0.016(2) 0.026(1) 0.010(1)
F(3) 4e 0.1098(2) 0.9241(2) 0.9697(2) 0.066(1) 0.177(2) 0.081(1) 0.038(2) 0.002(1) 0.023(1)
F(4) 4e 0.1702(2) 0.7796(2) 0.9340(3) 0.126(2) 0.095(2) 0.106(2) 0.042(2) 0.031(1) 0.020(1)
F(5) 4e 0.2653(2) 0.9845(2) 0.9885(3) 0.135(2) 0.082(2) 0.118(2) 0.032(1) 0.026(2) 0.010(1)
F(6) 4e 0.3257(2) 0.8387(2) 0.9516(3) 0.061(1) 0.143(2) 0.177(3) 0.029(1) 0.019(2) 0.011(2)
References
1. Ach, Μ.: 1,3-Dipolare Cycloaddition cyclischer Keten-iV.X-acetale mit Azidcn. Dissertation, Universität Würzburg, Germany 1992.
2. Quast, Η.; Ach, Μ.; Kindermann, Μ. Κ.; Rademacher, P.; Schindler, Μ.:
Synthese, NMR-Spektren und Photoelektronen-Spektren von cyclischen Keten-W.X-acetalen (2-Alkyliden-iV-heterocyclen). C h e m . Ber. 126 ( 1 9 9 3 ) 5 0 3 - 5 1 6 .
3. Peters, K.; Peters, E.-M.; Ach, M.; Quast, H.: Crystal structure 4 , 5 , 2 ' , 3 ' - t e t r a h y d r o - 4 - ( 1,1 - d i m e t h y l e t h y l ) - 1 , 1 ' , 3 ' - t r i m e t h y l s p i r o - lW][l,2,3]-triazole-5,2'-[l//]-benzimidazole. Z. Kristallogr. NCS 215 (2000) 297-298.
4. Sheldrick, G. M . : Program Package S H E L X T L - p l u s . Release 4.1.
Siemens Analytical X - R a y Instruments Inc., Madison (WI 53719), USA 1990.
