E.-M. Peters

Crystal structure of 2-amino-3-(4-fluorophenacyl)-5-methyl-1,3,4-oxadiazolium bromide, [C2N2O]+[NH2][CH3][(CH2CO)C6H4F]Br-

CiiHiiBrFN3C>2, triclinic, Ρ1 (No. 2), a = 5.114(1) Ä, b = 9.930(1) Ä, c = 12.966(2) Ä, α = 89.62(1)°, β = 82.48(1)°, γ = 88.57(1)°, V= 652.6 Ä, Ζ = 2, Rgl(F) = 0.037, wR(F) = 0.037, Γ =273 Κ. Source of material The title compound was synthesized by lh refluxing of equimolecular amounts of 2-amino-5-methyl-l,3,4-oxadiazole with 4-fluorophenacylbromide in ethanol; mp 546 Κ (decomp.) [1]. Table 3. Atomic coordinates and displacement parameters (in Ä). Atom Site X y ζ Uiso H(6A) 2i 0.2164(6) 0.4750(3) 0.7577(2) 0.08 H(6B) 2 i 0.3903(6) 0.5439(3) 0.8323(2) 0.08 H(9) 2i 0.8476(7) 0.5925(4) 0.5116(2) 0.08 H(10) 2i 0.7459(9) 0.7695(4) 0.3991(3) 0.08 H(12) 2 i 0.0851(8) 0.8628(4) 0.5954(3) 0.08 H(13) 2 i 0.1905(7) 0.6918(3) 0.7094(3) 0.08 H(14A) 2 i 0.8906 0.3515 0.9785 0.11(2) H(14B) 2 i 0.7798 0.4798 0.9129 0.07(1) H(15A) 2 i 0.2161(9) -0.0207(4) 0.8086(4) 0.08 H(15B) 2 i 0.3045(9) -0.0319(4) 0.9197(4) 0.08 H(15C) 2 i 0.5097(9) -0.0592(4) 0.8208(4) 0.08 Atom Site χ y ζ U n U22 i/33 U12 U13 i/23 Br(l) 2 i -0.16306(7) 0.71394(3) 0.90166(2) 0.0563(2) 0.0453(2) 0.0538(2) 0.0035(1) -0.0076(1) 0.0037(1) N(l) 2 i 0.4451(5) 0.3458(3) 0.8240(2) 0.046(1) 0.039(1) 0.045(1) 0.000(1) -0.008(1) 0.008(1) C(2) 2 i 0.6268(6) 0.3118(3) 0.8832(2) 0.047(2) 0.042(2) 0.041(1) 0.004(1) -0.000(1) 0.006(1) 0(3) 2i 0.6220(4) 0.1794(2) 0.8969(2) 0.059(1) 0.040(1) 0.050(1) 0.005(1) -0.010(1) 0.0076(9) C(4) 21 0.4229(7) 0.1359(4) 0.8444(2) 0.065(2) 0.043(2) 0.052(2) 0.001(2) -0.012(2) 0.002(1) N(5) 2 1 0.3142(5) 0.2322(3) 0.7981(2) 0.060(2) 0.042(1) 0.050(1) -0.004(1) -0.012(1) 0.005(1) C(6) 2i 0.3882(6) 0.4761(3) 0.7799(2) 0.048(2) 0.039(2) 0.045(2) 0.003(1) -0.006(1) 0.009(1) C(7) 2 i 0.5910(6) 0.5102(3) 0.6868(2) 0.043(2) 0.042(2) 0.044(1) -0.004(1) -0.007(1) 0.003(1) 0(7) 2 i 0.7949(4) 0.4446(3) 0.6708(2) 0.052(1) 0.059(1) 0.060(1) 0.010(1) 0.002(1) 0.010(1) C(8) 2 i 0.5262(6) 0.6240(3) 0.6205(2) 0.050(2) 0.039(2) 0.041(1) -0.007(1) -0.010(1) 0.003(1) C(9) 2i 0.6914(7) 0.6476(4) 0.5290(2) 0.064(2) 0.049(2) 0.046(2) -0.009(2) -0.007(1) 0.005(1) C(10) 2 i 0.6311(9) 0.7513(4) 0.4621(3) 0.095(3) 0.059(2) 0.042(2) -0.019(2) -0.010(2) 0.009(2) C(ll) 2i 0.4090(9) 0.8251(4) 0.4880(3) 0.100(3) 0.041(2) 0.059(2) -0.012(2) -0.032(2) 0.013(2) C(12) 2/ 0.2406(8) 0.8069(4) 0.5789(3) 0.075(2) 0.044(2) 0.076(2) 0.004(2) -0.019(2) 0.008(2) C(13) 2 i 0.3029(7) 0.7059(3) 0.6451(3) 0.061(2) 0.045(2) 0.056(2) -0.002(2) -0.006(2) 0.007(1) N(14) 2i 0.7863(5) 0.3858(3) 0.9255(2) 0.051(2) 0.048(2) 0.062(2) -0.005(1) -0.018(1) 0.009(1) C(15) 2i 0.3578(9) -0.0061(4) 0.8488(4) 0.110(3) 0.044(2) 0.098(3) -0.003(2) -0.031(3) 0.010(2) F(l) 2 i 0.3446(6) 0.9215(3) 0.4210(2) 0.151(2) 0.063(2) 0.085(2) -0.002(2) -0.039(2) 0.035(1) * Correspondence author (e-mail: peters@vsibml.mpi-stuttgart.mpg.de) 382 2-Amino-3-(4-fluorophenacyl)-5-methyl-l ,3,4-oxadiazolium bromide References 1. Hetzheim, Α.: Unpublished results. 2. Sheldrick, G. M.: Program Package SHELXTL-Plus. Release 4.1, Siemens Analytical X-Ray Instruments Inc., Madison (WI 53719), USA 1990.

Crystal structure of 1-acetylamino-2-pyrrolidino-4-tert-butylimidazole, (C4H9)(C2H4N0)(C4H8N)C3HN2

H(3) 16/ 0.1587(2) 0.5574(2) 0.0952(2) 0.08 H(7A) 16/ 0.4135(2) 0.5833(2) 0.1498(2) 0.08 H(7B) 16/ 0.4378(2) 0.5095(2) 0.1122(2) 0.08 H(8A) 16/ 0.5449(2) 0.5555(3) 0.0899(3) 0.08 H(8B) 16/ 0.5204(2) 0.6294(3) 0.1272(3) 0.08 H(9A) 16/ 0.5261(2) 0.6747(3) 0.0197(3) 0.08 H(9B) 16/ 0.5406(2) 0.5987(3) -0.0188(3) 0.08 H(10A) 16/ 0.4337(2) 0.6071(2) -0.0669(2) 0.08 H(10B) 16/ 0.4145(2) 0.6744(2) -0.0150(2) 0.08 H ( l l ) 16/ 0.296(2) 0.499(2) 0.182(2) 0.056(9) H(13A) 16/ 0.3138(2) 0.3208(2) 0.1319(2) 0.08 H(13B) 16/ 0.2774(2) 0.3655(2) 0.1987(2) 0.08 H(13C) 16/ 0.3601(2) 0.3769(2) 0.1794(2) 0.08 H(15A) 16/ 0.0711(2) 0.6494(2) 0.0603(2) 0.08 H(15B) 16/ 0.0672(2) 0.5968(2) -0.0109(2) 0.08 H(15C) 16/ 0.0383(2) 0.6769(2) -0.0180(2) 0.08 H(16A) 16/ 0.1486(2) 0.6162(2) -0.1247(2) 0.08 H(16B) 16/ 0.2027(2) 0.6823(2) -0.1256(2) 0.08 H(16C) 16/ 0.1186(2) 0.6958(2) -0.1319(2) 0.08 H(17A) 16/ 0.1248(2) 0.7801(2) -0.0204(2) 0.08 H(17B) 16/ 0.2089(2) 0.7665(2) -0.0141(2) 0.08 H(17C) 16/ 0.1587(2) 0.7541(2) 0.0579(2) 0.08

Crystal structure of 3,4-diphenyl-6-methyl-1-propargylaminoímidazo[1,5-b]pyridazine, (C6H5)2C7H4N3(C3H4N)

C22H18N4, triclinic, PI (No. 2), a = 8.667(1) k,b = 9.781(1) Â, c = 22.097(2) Â, α = 79.53(1)°, β = 86.62(1)°, γ = 78.09(1)°, V = 1801.9 À*, Ζ = 4, Rgt(F) = 0.057, ÄW(F) = 0.059, T= 293 K.

Crystal structure of 2,4-dimethyl-5-(4-methoxyphenyÍ)- 7-pyrid-3-ylmethylaminoimidazo[1,5-b]- pyridazine, C6HN3(C6H7N2)(C7H7O)(CH3)2

C21H21N5O, triclinic, P I (No. 2), a = 8 .606(2) Â , b = 9 .852(3) Â , c = 22 .056(4) À, α = 99.11(2)° , β = 98 .41(1)° , γ = 94 .20(1)° , V = 1817 .7 Λ 3 , Ζ = 4 , RgríF) = 0 . 0 7 2 , RW(F) = 0 . 0 6 7 , 7 = 2 9 3 Κ.

Crystal structure of 1-(2,5-dimethylpyrrolidino)-4-(4- methoxyphenyl)-imidazole-2(1/H)-thione, C16H17N3OS

C16H17N3OS, monoclinic, P12i/cl (No. 14), a = 11.324(1) Ä, b= 13.552(1) Ä , c = 11.131(1) Α, β = 111.18(1)°, V= 1592.8 Ä, Z = 4, Rgl(F) = 0.065, Rw(F) = 0.068, T= 293 K. Source of material The title compound was synthesized by reaction of 1 -amino-4-(4ethoxyphenyl)imidazole-2(l/i)-thione with acetonylacetone [1]. Discussion Two intermolecular Η bridges (H2-S1 = 252 pm) arround the origin of the unit cell form an isolated pait of the asymmetric unit. Table 2. Atomic coordinates and displacement parameters (in Ä). Atom Site X y ζ t/i so H(2) Ae 0.071(3) 0.585(2) 0.090(3) 0.08(1) H(4) Ae 0.3685(3) 0.6144(2) 0.4034(3) 0.08 H(8) Ae 0.5760(4) 0.2715(3) 0.3327(4) 0.08 H(9) Ae 0.4685(4) 0.2204(3) 0.4856(4) 0.08 H(12) Ae 0.0879(3) 0.7488(2) 0.0393(3) 0.08 H(13) Ae 0.0540(3) 0.9170(2) 0.0207(3) 0.08 H(15) Ae 0.2245(3) 0.9491(2) 0.4071(3) 0.08 H(16) Ae 0.2587(3) 0.7785(2) 0.4269(3) 0.08 H(17A) Ae 0.1476(4) 1.1795(2) 0.2540(4) 0.08 H(17B) Ae 0.2642(4) 1.1083(2) 0.3052(4) 0.08 H(17C) Ae 0.1547(4) 1.1008(2) 0.3596(4) 0.08 H(18A) Ae 0.5491(4) 0.4244(4) 0.1695(4) 0.08 H(18B) Ae 0.5096(4) 0.5183(4) 0.2282(4) 0.08 H(18C) Ae 0.4074(4) 0.4589(4) 0.1185(4) 0.08 H(19A) Ae 0.2736(4) 0.3005(3) 0.5463(4) 0.08 H(19B) Ae 0.1822(4) 0.3582(3) 0.4268(4) 0.08 H(19C) Ae 0.2818(4) 0.4158(3) 0.5409(4) 0.08 Table 3. Atomic coordinates and displacement parameters (in A). Atom Site X y ζ Uu U22 C/33 Un Un i/23 S( l ) Ae 0.12472(8) 0.37466(6) 0.10231(8) 0.0717(5) 0.0555(5) 0.0733(5) 0.0021(4) -0.0052(4) —0.0092(4) C ( l ) Ae 0.1783(3) 0.4796(2) 0.1817(3) 0.052(1) 0.058(2) 0.059(2) 0.002(1) 0.006(1) —0.001(1) N(2) Ae 0.1315(2) 0.5714(2) 0.1561(2) 0.054(1) 0.057(1) 0.063(2) 0.002(1) -0.002(1) -0.005(1) C(3) Ae 0.2052(3) 0.6393(2) 0.2457(3) 0.057(2) 0.053(2) 0.063(2) -0.004(1) 0.010(1) -0.004(1) C(4) Ae 0.3009(3) 0.5885(2) 0.3302(3) 0.057(2) 0.056(2) 0.062(2) -0.002(1) 0.005(1) -0.007(1) N(5) Ae 0.2826(2) 0.4906(2) 0.2908(2) 0.054(1) 0.056(1) 0.063(1) 0.001(1) 0.004(1) -0.004(1) N(6) Ae 0.3687(2) 0.4163(2) 0.3421(2) 0.053(1) 0.059(1) 0.067(2) 0.006(1) 0.004(1) -0.000(1) C(7) Ae 0.4595(3) 0.3911(3) 0.2905(4) 0.057(2) 0.089(2) 0.083(2) 0.008(2) 0.002(2) -0.013(2) C(8) Ae 0.5094(4) 0.3067(3) 0.3482(4) 0.064(2) 0.098(3) 0.117(3) 0.025(2) -0.007(2) -0.027(3) * Correspondence author (e-mail: karpet@vsibml.mpi-stuttgart.mpg.de)

Crystal structure of 2,4-dimethyl-5-4'-methoxyphenyl-7-thioxoimidazo-[1,5-b]pyridazine, C6H2N3S(CH3)2C6H4OCH3

H(l) 4e 0.119(4) 0.479(4) 0.589(3) 0.15(2) H(5) 4e 0.6435(2) 0.2807(3) 0.4872(2) 0.08 H(10) 4e 0.2041(3) 0.5767(3) 0.7382(2) 0.08 H(ll) 4e 0.1977(3) 0.5856(3) 0.9159(2) 0.08 H(13) 4e 0.4252(3) 0.2737(3) 0.9670(2) 0.08 H(14) 4c 0.4280(2) 0.2637(2) 0.7891(2) 0.08 H(15A) 4c 0.5651(2) 0.3528(3) 0.7326(2) 0.08 H(15B) 4c 0.6794(2) 0.3897(3) 0.6784(2) 0.08 H(15C) 4c 0.6461(2) 0.2473(3) 0.6916(2) 0.08 H(16A) 4c 0.6021(3) 0.2459(3) 0.3052(2) 0.08 H(16B) 4c 0.5071(3) 0.3446(3) 0.2407(2) 0.08 H(I6C) 4c 0.4596(3) 0.2066(3) 0.2541(2) 0.08 H(17A) 4c 0.2270(4) 0.4897(4) 1.1733(3) 0.08 H(17B) 4c 0.1323(4) 0.4856(4) 1.0637(3) 0.08 H(17C) 4c 0.2405(4) 0.5893(4) 1.0875(3) 0.08

Crystal structure of 2-amino-3-phenacyl-4,5-dimethyloxazolium bromide, [C3NO]+(NH2)(CH3)2[(CH2CO)C6H5]Br-

H(6A) 4e 0.018(5) -0.432(3) 0.611(3) 0.13(2) H(6B) Ae -0.162(4) -0.434(3) 0.535(3) 0.08(1) H(7A) 4e 0.1213(4) -0.3169(3) 0.7395(3) 0.08 H(7B) 4e 0.0985(4) -0.2174(3) 0.8074(3) 0.08 H(10) 4e 0.3586(4) -0.2571(3) 0.8740(3) 0.08 H(ll) 4e 0.6102(5) -0.2655(3) 0.9894(3) 0.08 H(12) 4e 0.6607(5) -0.3827(3) 1.1318(3) 0.08 H(13) 4e 0.4569(5) -0.4871(3) 1.1622(3) 0.08 H(14) 4e 0.2028(4) -0.4780(3) 1.0486(3) 0.08 H(15A) 4e -0.2703(5) -0.1138(3) 0.8541(3) 0.08 H(15B) 4e -0.1032(5) -0.0958(3) 0.8393(3) 0.08 H(15C) 4e -0.1318(5) -0.1914(3) 0.9096(3) 0.08 H(16A) 4e -0.5213(4) -0.1537(3) 0.7199(4) 0.08 H(16B) 4e -0.5824(4) -0.2660(3) 0.6675(4) 0.08 H(16C) 4e -0.5430(4) -0.1702(3) 0.6014(4) 0.08

Crystal structure of 1-acetylamino-2-(2'-ethoxycarbonyl-1'-methyl)- hydrazino-4-phenylimidazole, [C6H5][NH(CO)CH3][N(CH3)NH(C00C2H5)]C3N2H

H(2) 4c -0.6182(5) -0.1470(3) 0.1389(1) 0.08 H(6) 4c -0.530(5) 0.069(4) 0.235(1) 0.06(1) H(8A) 4c -0.5254(5) -0.1757(4) 0.3276(1) 0.08 H(8B) 4c -0.6812(5) -0.0697(4) 0.3040(1) 0.08 H(8C) 4c -0.4767(5) -0.0088(4) 0.3212(1) 0.08 H(9A) 4c 0.0253(5) 0.2110(4) 0.1335(1) 0.08 H(9B) 4c 0.1581(5) 0.0919(4) 0.1589(1) 0.08 H(9C) 4c 0.1268(5) 0.2441(4) 0.1846(1) 0.08 H(10) 4c -0.001(5) -0.039(4) 0.237(1) 0.06(1) H(13A) 4« -0.1163(8) 0.1849(4) 0.3693(1) 0.08 H(13B) 4c 0.1068(8) 0.2117(4) 0.3589(1) 0.08 H{14A) 4c 0.0677(9) 0.1011(5) 0.4328(1) 0.08 H(14B) 4c 0.1806(9) -0.0024(5) 0.3965(1) 0.08 H(14C) 4c -0.0425(9) -0.0291(5) 0.4068(1) 0.08 H(16) 4c -0.1200(8) -0.0729(6) 0.0267(2) 0.08 H(17) 4c -0.150(1) -0.1684(8) -0.0531(2) 0.08 H(18) 4c -0.424(1) -0.2942(8) -0.0783(2) 0.08 H(19) 4c -0.673(1) -0.3226(8) -0.0240(2) 0.08 H(20) 4c -0.6538(9) -0.2341(7) 0.0562(2) 0.08