data_2007173 _journal_name_full 'Acta Crystallographica' _journal_year 1998 _journal_volume C54 _journal_page_first 509 _journal_page_last 513 _publ_section_title ; Nonstereospecific 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides -- Proof of Structure for four Diastereoisomeric (3+2) Cycloadducts ; loop_ _publ_author_name 'Breu, Josef' 'Range, Klaus-J\"urgen' 'Weber, Andreas' 'Sauer, J\"urgen' _chemical_formula_moiety 'C29 H33 N5' _chemical_formula_sum 'C29 H33 N5' _chemical_formula_weight 451.61 _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z _cell_length_a 16.246(3) _cell_length_b 10.8936(8) _cell_length_c 20.173(3) _cell_angle_alpha 90 _cell_angle_beta 134.282(9) _cell_angle_gamma 90 _cell_volume 2555.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 200 _exptl_crystal_density_diffrn 1.174 _diffrn_ambient_temperature 200 _refine_ls_R_factor_obs .0480 _refine_ls_wR_factor_obs .1252 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy N3 .0833(2) .4933(2) .42345(15) .0534(9) Uani 1.000 N5 .3308(2) .2903(2) .66993(14) .0553(9) Uani 1.000 N12 .2545(2) .31902(14) .43583(11) .0343(6) Uani 1.000 N13 .2184(2) .22372(14) .45599(10) .0322(6) Uani 1.000 N44 -.0190(2) .2330(2) .44140(12) .0406(6) Uani 1.000 C1 .1684(2) .2723(2) .48908(13) .0345(8) Uani 1.000 C2 .1196(2) .3971(2) .45172(14) .0389(9) Uani 1.000 C4 .2606(2) .2827(2) .59189(14) .0381(9) Uani 1.000 C6 .2472(2) .0850(2) .32986(14) .0385(8) Uani 1.000 C7 .2247(3) .0102(2) .2550(2) .0502(9) Uani 1.000 C8 .3694(3) .0748(2) .42222(15) .0481(9) Uani 1.000 C11 .2426(2) .3116(2) .36636(13) .0356(8) Uani 1.000 C14 .1545(2) .1110(2) .39856(13) .0317(8) Uani 1.000 C15 .1468(2) .1019(2) .31929(13) .0351(8) Uani 1.000 C16 .1870(2) .2084(2) .29998(13) .0370(8) Uani 1.000 C21 .2923(2) .4149(2) .35559(14) .0377(8) Uani 1.000 C22 .3159(3) .4042(2) .30253(15) .0431(9) Uani 1.000 C23 .3657(3) .5001(2) .2959(2) .0455(9) Uani 1.000 C24 .3922(3) .6099(2) .34174(15) .0447(9) Uani 1.000 C25 .3665(3) .6211(2) .3935(2) .0516(9) Uani 1.000 C26 .3165(3) .5260(2) .4004(2) .0491(9) Uani 1.000 C27 .4490(3) .7133(2) .3357(2) .0603(12) Uani 1.000 C31 .2151(2) -.0031(2) .46026(13) .0326(8) Uani 1.000 C32 .1640(2) -.1172(2) .42133(14) .0377(8) Uani 1.000 C33 .2156(2) -.2237(2) .47210(14) .0409(9) Uani 1.000 C34 .3197(2) -.2218(2) .56361(14) .0413(9) Uani 1.000 C35 .3706(3) -.1079(2) .60259(14) .0436(9) Uani 1.000 C36 .3188(2) -.0007(2) .55201(14) .0391(8) Uani 1.000 C37 .3767(3) -.3389(2) .6187(2) .0607(9) Uani 1.000 C41 -.0422(2) .2164(2) .28318(14) .0435(9) Uani 1.000 C42 .0369(2) .1293(2) .36572(13) .0339(8) Uani 1.000 C43 .0720(2) .1785(2) .45408(13) .0342(8) Uani 1.000 C45 -.1130(3) .1455(2) .3995(2) .0532(11) Uani 1.000 C46 .0214(3) .2762(3) .5286(2) .0574(12) Uani 1.000 H7A .2368(17) -.0771(3) .2713(7) .0750 Uiso 1.000 H7B .2777(11) .0363(12) .2497(9) .0750 Uiso 1.000 H7C .1453(5) .0231(14) .1957(3) .0750 Uiso 1.000 H8A .4215(3) .1034(15) .4166(3) .0720 Uiso 1.000 H8B .3867(5) -.0110(3) .4426(6) .0720 Uiso 1.000 H8C .3796(4) .1254(13) .4677(3) .0720 Uiso 1.000 H15 .0742(2) .0630(2) .26222(13) .0420 Uiso 1.000 H16 .1370(2) .2307(2) .23338(13) .0450 Uiso 1.000 H22 .2978(3) .3301(2) .26989(15) .0520 Uiso 1.000 H23 .3821(3) .4903(2) .2592(2) .0550 Uiso 1.000 H25 .3836(3) .6958(2) .4253(2) .0620 Uiso 1.000 H26 .2985(3) .5365(2) .4359(2) .0590 Uiso 1.000 H27A .4363(15) .7016(10) .2810(8) .0900 Uiso 1.000 H27B .5317(4) .7135(11) .3914(7) .0900 Uiso 1.000 H27C .4156(12) .7919(3) .3307(13) .0900 Uiso 1.000 H32 .0922(2) -.1216(2) .35863(14) .0450 Uiso 1.000 H33 .1787(2) -.3002(2) .44355(14) .0490 Uiso 1.000 H35 .4424(3) -.1037(2) .66530(14) .0520 Uiso 1.000 H36 .3552(2) .0759(2) .58081(14) .0460 Uiso 1.000 H37A .3951(18) -.3902(10) .5906(10) .0910 Uiso 1.000 H37B .3243(8) -.3835(10) .6187(13) .0910 Uiso 1.000 H37C .4475(11) -.3189(2) .6825(5) .0910 Uiso 1.000 H41A -.1061(8) .2414(13) .2758(7) .0650 Uiso 1.000 H41B -.0724(13) .1745(6) .2269(3) .0650 Uiso 1.000 H41C .0013(4) .2892(8) .2939(6) .0650 Uiso 1.000 H42 -.0019(2) .0479(2) .34920(13) .0410 Uiso 1.000 H43 .1072(2) .1102(2) .50001(13) .0410 Uiso 1.000 H45A -.1744(7) .1854(5) .3903(11) .0800 Uiso 1.000 H45B -.0841(4) .0746(8) .4405(6) .0800 Uiso 1.000 H45C -.1433(10) .1182(12) .3396(6) .0800 Uiso 1.000 H46A -.0436(4) .3090(18) .5174(3) .0860 Uiso 1.000 H46B .0789(13) .3408(14) .5545(7) .0860 Uiso 1.000 H46C .0560(17) .2077(5) .5724(5) .0860 Uiso 1.000 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N3 .062(2) .0319(11) .0723(13) -.0007(10) .0491(12) -.0010(9) N5 .051(2) .0754(14) .0411(12) -.0068(12) .0327(11) -.0076(9) N12 .0416(14) .0286(8) .0385(9) -.0033(8) .0301(9) -.0003(7) N13 .0417(13) .0279(8) .0340(8) -.0063(8) .0290(8) -.0034(6) N44 .0398(14) .0375(9) .0504(10) -.0032(9) .0337(10) -.0042(8) C1 .045(2) .0295(10) .0346(10) -.0035(9) .0298(11) -.0026(8) C2 .045(2) .0323(12) .0443(12) -.0051(10) .0330(11) -.0055(9) C4 .040(2) .0438(12) .0367(12) -.0051(10) .0291(11) -.0039(9) C6 .046(2) .0357(11) .0397(11) -.0008(10) .0321(11) -.0029(8) C7 .067(2) .0446(13) .0572(14) -.0053(12) .0500(14) -.0095(10) C8 .049(2) .0476(13) .0484(13) .0044(12) .0343(12) .0029(10) C11 .044(2) .0307(11) .0355(11) .0002(10) .0290(10) .0013(8) C14 .036(2) .0248(10) .0318(10) -.0046(9) .0227(10) -.0032(7) C15 .041(2) .0307(10) .0318(10) -.0031(9) .0248(10) -.0023(7) C16 .045(2) .0352(11) .0322(10) -.0008(10) .0275(10) .0010(8) C21 .045(2) .0325(11) .0397(11) .0007(10) .0311(11) .0046(8) C22 .056(2) .0354(11) .0461(12) .0008(10) .0386(12) .0010(9) C23 .055(2) .0469(13) .0509(12) .0035(12) .0429(13) .0068(10) C24 .046(2) .0407(12) .0457(12) -.0054(11) .0314(12) .0050(9) C25 .074(2) .0370(12) .0578(14) -.0137(12) .0511(15) -.0074(10) C26 .075(2) .0360(12) .0592(14) -.0084(12) .0552(15) -.0064(10) C27 .064(2) .057(2) .068(2) -.0148(14) .049(2) .0014(12) C31 .038(2) .0312(10) .0340(10) -.0005(9) .0271(10) -.0014(7) C32 .043(2) .0333(11) .0340(10) -.0004(10) .0259(10) -.0028(8) C33 .053(2) .0286(11) .0446(12) -.0017(10) .0354(12) -.0031(8) C34 .054(2) .0345(11) .0418(12) .0092(10) .0358(12) .0063(9) C35 .047(2) .0409(12) .0361(11) .0037(11) .0265(11) .0022(9) C36 .043(2) .0343(11) .0365(11) -.0020(10) .0265(11) -.0013(8) C37 .076(2) .0365(13) .0538(14) .0154(12) .0395(14) .0094(10) C41 .043(2) .0409(12) .0374(11) .0041(11) .0247(11) .0033(9) C42 .036(2) .0269(10) .0344(10) -.0021(9) .0230(10) -.0003(8) C43 .036(2) .0330(10) .0372(11) -.0016(10) .0269(10) .0010(8) C45 .044(2) .0538(14) .067(2) -.0048(12) .0407(14) -.0044(11) C46 .062(2) .067(2) .066(2) -.0089(15) .053(2) -.0167(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N3 C2 . . 1.141(3) no N5 C4 . . 1.131(3) no N12 N13 . . 1.386(4) no N12 C11 . . 1.277(4) no N13 C1 . . 1.464(5) no N13 C14 . . 1.499(3) no N44 C43 . . 1.441(5) no N44 C45 . . 1.467(5) no N44 C46 . . 1.461(4) no C1 C2 . . 1.487(3) no C1 C4 . . 1.490(3) no C1 C43 . . 1.566(4) no C6 C7 . . 1.519(4) no C6 C8 . . 1.503(4) no C6 C15 . . 1.501(5) no C6 C16 . . 1.518(3) no C11 C16 . . 1.478(3) no C11 C21 . . 1.487(4) no C14 C15 . . 1.518(4) no C14 C31 . . 1.534(3) no C14 C42 . . 1.537(5) no C15 C16 . . 1.510(4) no C21 C22 . . 1.371(6) no C21 C26 . . 1.393(3) no C22 C23 . . 1.384(6) no C23 C24 . . 1.384(3) no C24 C25 . . 1.374(7) no C24 C27 . . 1.514(6) no C25 C26 . . 1.382(6) no C31 C32 . . 1.393(3) no C31 C36 . . 1.382(3) no C32 C33 . . 1.378(3) no C33 C34 . . 1.382(3) no C34 C35 . . 1.391(3) no C34 C37 . . 1.511(3) no C35 C36 . . 1.383(3) no C41 C42 . . 1.528(3) no C42 C43 . . 1.540(3) no C7 H7A . . .980(5) no C7 H7B . . .98(2) no C7 H7C . . .980(7) no C8 H8A . . .980(9) no C8 H8B . . .980(5) no C8 H8C . . .980(10) no C15 H15 . . 1.000(3) no C16 H16 . . 1.000(3) no C22 H22 . . .949(3) no C23 H23 . . .952(7) no C25 H25 . . .950(4) no C26 H26 . . .951(7) no C27 H27A . . .979(19) no C27 H27B . . .980(11) no C27 H27C . . .980(14) no C32 H32 . . .950(3) no C33 H33 . . .951(3) no C35 H35 . . .950(4) no C36 H36 . . .951(3) no C37 H37A . . .98(2) no C37 H37B . . .98(2) no C37 H37C . . .980(9) no C41 H41A . . .979(17) no C41 H41B . . .980(8) no C41 H41C . . .981(10) no C42 H42 . . 1.001(4) no C43 H43 . . 1.000(3) no C45 H45A . . .980(18) no C45 H45B . . .979(9) no C45 H45C . . .980(11) no C46 H46A . . .980(11) no C46 H46B . . .979(18) no C46 H46C . . .980(7) no