Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_Z-6d _database_code_CSD 165720 _audit_creation_method Xtal3.6 _audit_creation_date 00-04-03 _journal_coden_Cambridge 207 loop_ _publ_author_name 'Kocevar, Marijan' 'Meden, Anton' 'Polanc, Slovenko' 'Vranicar, Lidija' _publ_requested_journal 'Perkin Transactions 1' # 1. SUBMISSION DETAILS #---------------------- _publ_contact_author_name 'Prof Marijan Kocevar' _publ_contact_author_address ; Faculty of Chemistry and Chemical Technology University of Ljubljana Askerceva 5 Ljubljana SI-1000 SLOVENIA ; _publ_contact_author_email MARIJAN.KOCEVAR@UNI-LJ.SI _publ_contact_author_fax '+386 1 2419 104' _publ_contact_author_phone '+386 1 2419 144' _publ_section_title ; Alpha,Beta-Didehydroamino acid derivatives with isoxazolyl or pyrazolyl moiety: The effect of substituents and reaction conditions on their stereoselective formation from 2H-pyran-2-ones. ; #======================================================================= # Data block for single structure (one for each study in the #paper) #======================================================================= # 2. EXPERIMENTAL DATA #--------------------- _chemical_name_systematic ; N-{(Z)-2-[3-methyl-5-phenyl-1-(1,2,4-triazolo[4,3-b]pyridazin-6-yl) -1H-pyrazol-4-yl]ethenyl}benzamide ; _chemical_name_common ? _chemical_formula_sum 'C24 H19 N7 O1' _chemical_formula_moiety 'C24 H19 N7 O1' _chemical_formula_weight 421.46 _exptl_crystal_colour 'yellow' _chemical_melting_point 503 _exptl_crystal_description 'prism' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_preparation 'DMF/EtOH' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C_1_2/c_1 _symmetry_space_group_name_Hall -c_2yc loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,+y,1/2-z -x,-y,-z +x,-y,1/2+z 1/2+x,1/2+y,+z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 24.8950(10) _cell_length_b 16.4810(10) _cell_length_c 10.2980(10) _cell_angle_alpha 90.00000 _cell_angle_beta 93.967(9) _cell_angle_gamma 90.00000 _cell_volume 4215.1(5) _cell_formula_units_Z 8 _exptl_crystal_density_diffrn 1.328 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_radiation_monochromator 'graphite' _cell_measurement_reflns_used 12461 # Cell determined from CCD image data! _cell_measurement_theta_min 1 # Cell determined from CCD image data! _cell_measurement_theta_max 26.37 # Cell determined from CCD image data! _cell_measurement_temperature 293 _exptl_crystal_F_000 1760 _exptl_absorpt_coefficient_mu .087 _diffrn_measurement_device_type CCD _diffrn_measurement_method 'Phi, omega scans' _exptl_absorpt_correction_type none _diffrn_reflns_number 12461 _reflns_number_total 4253 _reflns_Friedel_coverage 0 _reflns_number_gt 2722 _reflns_threshold_expression 'F > 3.00 sig(F )' _diffrn_reflns_theta_max 26.37 _diffrn_reflns_av_R_equivalents .1 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .066 _refine_ls_wR_factor_ref .045 _refine_ls_R_factor_all .115 _refine_ls_wR_factor_all .052 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_number_reflns 2722 _refine_ls_number_parameters 365 _refine_ls_weighting_scheme 'calc, Regina' _refine_ls_hydrogen_treatment refall _refine_ls_shift/su_max .0035 _refine_diff_density_min -.376 _refine_diff_density_max .403 _atoms_sites_solution_primary 'direct methods' _atoms_sites_solution_secondary 'Fourier difference' _computing_data_collection 'Nonius Kappa CCD collection software' _computing_cell_refinement 'DENZO SCALEPACK' _computing_data_reduction 'DENZO SCALEPACK xtal ADDREF SORTRF' _computing_structure_solution 'SIR92' _computing_structure_refinement 'xtal CRYLSQ' _computing_molecular_graphics 'ORTEP included in xtal' _computing_publication_material 'xtal BONDLA CIFIO' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O .94276(8) .12447(13) -.1304(2) .0792(13) Uani ? ? 1.00000 ? ? N1 .64710(9) .21926(13) .7832(2) .0600(14) Uani ? ? 1.00000 ? ? N2 .69449(10) .21208(13) .8607(2) .0593(14) Uani ? ? 1.00000 ? ? N3 .70964(8) .18221(11) .65843(17) .0433(12) Uani ? ? 1.00000 ? ? N4 .73516(8) .16066(11) .55076(16) .0450(12) Uani ? ? 1.00000 ? ? N5 .81377(8) .11925(11) .46924(17) .0427(12) Uani ? ? 1.00000 ? ? N6 .86905(8) .12316(12) .48284(18) .0487(13) Uani ? ? 1.00000 ? ? N7 .90565(8) .15511(15) .0556(2) .0488(13) Uani ? ? 1.00000 ? ? C1 .65706(12) .20101(15) .6643(3) .0526(18) Uani ? ? 1.00000 ? ? C2 .73188(11) .18977(14) .7832(2) .0472(16) Uani ? ? 1.00000 ? ? C3 .78711(12) .17383(17) .8032(3) .0583(18) Uani ? ? 1.00000 ? ? C4 .81392(13) .15109(16) .7007(2) .0530(18) Uani ? ? 1.00000 ? ? C5 .78576(10) .14471(13) .5754(2) .0400(14) Uani ? ? 1.00000 ? ? C6 .79559(10) .09643(13) .3444(2) .0404(14) Uani ? ? 1.00000 ? ? C7 .84073(10) .08830(14) .2761(2) .0436(14) Uani ? ? 1.00000 ? ? C8 .88515(10) .10370(14) .3671(2) .0453(15) Uani ? ? 1.00000 ? ? C9 .94360(12) .0946(3) .3493(4) .064(2) Uani ? ? 1.00000 ? ? C10 .73945(9) .07820(14) .2998(2) .0412(14) Uani ? ? 1.00000 ? ? C11 .71668(11) .11442(17) .1876(2) .0495(16) Uani ? ? 1.00000 ? ? C12 .66462(12) .0977(2) .1438(3) .063(2) Uani ? ? 1.00000 ? ? C13 .63483(14) .0424(2) .2084(3) .066(2) Uani ? ? 1.00000 ? ? C14 .65734(12) .0041(2) .3167(3) .0607(19) Uani ? ? 1.00000 ? ? C15 .70883(11) .02187(16) .3629(3) .0515(16) Uani ? ? 1.00000 ? ? C16 .84234(12) .06071(17) .1418(2) .0510(16) Uani ? ? 1.00000 ? ? C17 .87214(11) .08777(17) .0493(3) .0518(17) Uani ? ? 1.00000 ? ? C18 .93975(10) .17110(18) -.0392(3) .0534(17) Uani ? ? 1.00000 ? ? C19 .97372(10) .24526(17) -.0272(2) .0504(15) Uani ? ? 1.00000 ? ? C20 1.01902(12) .2478(2) -.0984(3) .0622(19) Uani ? ? 1.00000 ? ? C21 1.05071(14) .3158(3) -.0979(3) .075(2) Uani ? ? 1.00000 ? ? C22 1.03848(15) .3822(3) -.0252(4) .082(2) Uani ? ? 1.00000 ? ? C23 .99416(15) .3803(2) .0489(4) .084(2) Uani ? ? 1.00000 ? ? C24 .96237(14) .3117(2) .0478(3) .068(2) Uani ? ? 1.00000 ? ? H1 .6318(10) .2011(13) .590(3) .049(7) Uiso ? ? 1.00000 ? ? H3 .8039(11) .1827(16) .888(3) .072(8) Uiso ? ? 1.00000 ? ? H4 .8502(15) .140(2) .708(3) .088(11) Uiso ? ? 1.00000 ? ? H7 .9011(10) .1880(16) .113(3) .048(8) Uiso ? ? 1.00000 ? ? H11 .7394(10) .1510(16) .144(2) .055(7) Uiso ? ? 1.00000 ? ? H12 .6491(11) .1250(16) .065(3) .065(8) Uiso ? ? 1.00000 ? ? H13 .5982(14) .0338(17) .176(3) .077(9) Uiso ? ? 1.00000 ? ? H14 .6371(11) -.0336(17) .361(2) .063(8) Uiso ? ? 1.00000 ? ? H15 .7251(9) -.0048(14) .433(2) .041(6) Uiso ? ? 1.00000 ? ? H16 .8181(11) .0210(18) .119(2) .061(8) Uiso ? ? 1.00000 ? ? H17 .8709(8) .0630(14) -.032(3) .046(7) Uiso ? ? 1.00000 ? ? H20 1.0261(11) .1987(19) -.147(3) .067(9) Uiso ? ? 1.00000 ? ? H21 1.0845(16) .314(2) -.150(3) .105(11) Uiso ? ? 1.00000 ? ? H22 1.0605(17) .431(3) -.020(3) .113(13) Uiso ? ? 1.00000 ? ? H24 .9308(12) .3131(15) .097(2) .065(8) Uiso ? ? 1.00000 ? ? H25 .9836(16) .427(3) .106(4) .122(13) Uiso ? ? 1.00000 ? ? H9a .9630(13) .0875(18) .440(4) .088(9) Uiso ? ? 1.00000 ? ? H9b .9564(13) .146(2) .315(3) .091(11) Uiso ? ? 1.00000 ? ? H9c .9499(16) .057(3) .291(4) .118(15) Uiso ? ? 1.00000 ? ? 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 O .0875(15) .0943(15) .0599(12) -.0219(12) .0353(10) -.0192(11) N1 .0626(16) .0580(14) .0618(15) .0002(11) .0223(13) -.0064(11) N2 .0691(16) .0622(15) .0489(12) .0059(12) .0196(13) -.0019(10) N3 .0483(14) .0424(12) .0403(13) .0004(10) .0107(10) -.0029(9) N4 .0491(14) .0507(12) .0363(11) .0022(10) .0102(9) -.0019(9) N5 .0422(13) .0505(13) .0361(12) -.0021(9) .0094(9) -.0001(9) N6 .0430(14) .0567(14) .0472(13) -.0025(10) .0087(9) .0032(10) N7 .0557(14) .0514(14) .0411(12) -.0019(12) .0173(11) -.0068(11) C1 .0492(19) .0553(17) .0541(19) .0001(13) .0092(16) -.0058(13) C2 .059(2) .0455(15) .0385(15) .0017(13) .0104(13) -.0002(11) C3 .067(2) .073(2) .0340(16) .0056(15) .0008(14) -.0034(13) C4 .055(2) .0616(18) .0423(16) .0043(15) .0017(14) -.0000(12) C5 .0433(17) .0403(14) .0369(14) -.0021(12) .0072(12) .0028(10) C6 .0473(16) .0364(14) .0382(14) -.0036(11) .0087(12) .0011(10) C7 .0497(16) .0381(14) .0444(15) -.0045(12) .0138(13) .0005(11) C8 .0457(17) .0438(15) .0477(15) -.0014(11) .0127(13) .0024(11) C9 .049(2) .083(3) .062(2) -.0035(17) .0129(16) -.004(2) C10 .0453(15) .0407(14) .0386(14) -.0039(12) .0104(11) -.0046(11) C11 .0515(18) .0535(17) .0443(15) -.0050(14) .0082(14) -.0005(13) C12 .062(2) .078(2) .0478(17) .0021(18) -.0018(16) -.0049(15) C13 .047(2) .084(2) .065(2) -.0062(17) .0006(16) -.0191(18) C14 .056(2) .0622(19) .0648(19) -.0171(16) .0137(17) -.0023(15) C15 .0528(18) .0523(16) .0499(16) -.0040(15) .0073(14) .0038(14) C16 .0554(17) .0497(16) .0493(17) -.0089(15) .0134(13) -.0079(13) C17 .0614(18) .0518(17) .0433(17) -.0049(15) .0129(14) -.0082(14) C18 .0525(17) .067(2) .0423(15) .0024(15) .0122(13) .0012(14) C19 .0470(15) .0613(19) .0431(14) -.0009(15) .0044(12) .0110(13) C20 .0559(19) .083(2) .0484(15) -.0077(19) .0095(14) .0082(17) C21 .058(2) .099(3) .0686(19) -.016(2) .0100(17) .014(2) C22 .071(2) .083(3) .093(2) -.022(2) .002(2) .021(2) C23 .080(3) .066(2) .108(3) -.008(2) .020(2) -.001(2) C24 .058(2) .067(2) .082(2) -.0034(17) .0206(17) .0035(17) # 5. Molecular Geometry #---------------------- 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 #<< enter YES for value to be published O C18 . . 1.220(3) ? N1 N2 . . 1.383(3) ? N1 C1 . . 1.302(4) ? N2 C2 . . 1.320(4) ? N3 N4 . . 1.363(3) ? N3 C1 . . 1.351(4) ? N3 C2 . . 1.369(3) ? N4 C5 . . 1.295(3) ? N5 N6 . . 1.375(3) ? N5 C5 . . 1.401(3) ? N5 C6 . . 1.385(3) ? N6 C8 . . 1.323(3) ? N7 C17 . . 1.387(4) ? N7 C18 . . 1.363(4) ? N7 H7 . . .81(3) ? C1 H1 . . .96(2) ? C2 C3 . . 1.401(4) ? C3 C4 . . 1.341(4) ? C3 H3 . . .95(3) ? C4 C5 . . 1.429(3) ? C4 H4 . . .92(4) ? C6 C7 . . 1.372(3) ? C6 C10 . . 1.471(3) ? C7 C8 . . 1.422(3) ? C7 C16 . . 1.459(3) ? C8 C9 . . 1.487(4) ? C9 H9a . . 1.03(3) ? C9 H9b . . .98(4) ? C9 H9c . . .88(4) ? C10 C11 . . 1.387(3) ? C10 C15 . . 1.390(4) ? C11 C12 . . 1.371(4) ? C11 H11 . . .96(3) ? C12 C13 . . 1.376(5) ? C12 H12 . . .98(3) ? C13 C14 . . 1.367(4) ? C13 H13 . . .96(3) ? C14 C15 . . 1.368(4) ? C14 H14 . . .94(3) ? C15 H15 . . .92(2) ? C16 C17 . . 1.325(4) ? C16 H16 . . .91(3) ? C17 H17 . . .93(3) ? C18 C19 . . 1.486(4) ? C19 C20 . . 1.388(4) ? C19 C24 . . 1.381(4) ? C20 C21 . . 1.371(5) ? C20 H20 . . .98(3) ? C21 C22 . . 1.372(6) ? C21 H21 . . 1.03(4) ? C22 C23 . . 1.385(6) ? C22 H22 . . .97(4) ? C23 C24 . . 1.379(5) ? C23 H25 . . 1.01(4) ? C24 H24 . . .97(3) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag #<< enter YES for value to be published N2 N1 C1 . . . 108.2(2) ? N1 N2 C2 . . . 106.5(2) ? N4 N3 C1 . . . 127.2(2) ? N4 N3 C2 . . . 127.3(2) ? C1 N3 C2 . . . 105.5(2) ? N3 N4 C5 . . . 113.31(17) ? N6 N5 C5 . . . 117.08(18) ? N6 N5 C6 . . . 111.58(18) ? C5 N5 C6 . . . 131.1(2) ? N5 N6 C8 . . . 105.09(18) ? C17 N7 C18 . . . 121.6(2) ? C17 N7 H7 . . . 116.9(19) ? C18 N7 H7 . . . 120.9(19) ? N1 C1 N3 . . . 110.1(2) ? N1 C1 H1 . . . 126.6(16) ? N3 C1 H1 . . . 123.3(16) ? N2 C2 N3 . . . 109.7(2) ? N2 C2 C3 . . . 133.6(2) ? N3 C2 C3 . . . 116.7(2) ? C2 C3 C4 . . . 118.3(3) ? C2 C3 H3 . . . 118.1(17) ? C4 C3 H3 . . . 123.5(17) ? C3 C4 C5 . . . 119.4(3) ? C3 C4 H4 . . . 122.1(19) ? C5 C4 H4 . . . 118.4(19) ? N4 C5 N5 . . . 116.00(19) ? N4 C5 C4 . . . 124.9(2) ? N5 C5 C4 . . . 119.1(2) ? N5 C6 C7 . . . 106.0(2) ? N5 C6 C10 . . . 125.9(2) ? C7 C6 C10 . . . 127.9(2) ? C6 C7 C8 . . . 105.8(2) ? C6 C7 C16 . . . 126.4(2) ? C8 C7 C16 . . . 127.5(2) ? N6 C8 C7 . . . 111.5(2) ? N6 C8 C9 . . . 119.7(2) ? C7 C8 C9 . . . 128.6(2) ? C8 C9 H9a . . . 107.6(19) ? C8 C9 H9b . . . 108(2) ? C8 C9 H9c . . . 112(3) ? H9a C9 H9b . . . 107(3) ? H9a C9 H9c . . . 116(3) ? H9b C9 H9c . . . 106(4) ? C6 C10 C11 . . . 119.8(2) ? C6 C10 C15 . . . 122.0(2) ? C11 C10 C15 . . . 118.1(2) ? C10 C11 C12 . . . 120.7(3) ? C10 C11 H11 . . . 116.0(15) ? C12 C11 H11 . . . 123.3(15) ? C11 C12 C13 . . . 120.2(3) ? C11 C12 H12 . . . 119.3(16) ? C13 C12 H12 . . . 120.5(16) ? C12 C13 C14 . . . 119.7(3) ? C12 C13 H13 . . . 117.3(17) ? C14 C13 H13 . . . 123.0(17) ? C13 C14 C15 . . . 120.5(3) ? C13 C14 H14 . . . 120.0(16) ? C15 C14 H14 . . . 119.5(16) ? C10 C15 C14 . . . 120.8(3) ? C10 C15 H15 . . . 117.5(14) ? C14 C15 H15 . . . 121.7(14) ? C7 C16 C17 . . . 129.1(3) ? C7 C16 H16 . . . 114.2(16) ? C17 C16 H16 . . . 116.6(16) ? N7 C17 C16 . . . 126.9(3) ? N7 C17 H17 . . . 112.0(14) ? C16 C17 H17 . . . 121.0(14) ? O C18 N7 . . . 120.2(3) ? O C18 C19 . . . 121.2(2) ? N7 C18 C19 . . . 118.6(2) ? C18 C19 C20 . . . 117.4(3) ? C18 C19 C24 . . . 124.2(3) ? C20 C19 C24 . . . 118.5(3) ? C19 C20 C21 . . . 120.8(3) ? C19 C20 H20 . . . 115.3(17) ? C21 C20 H20 . . . 123.9(17) ? C20 C21 C22 . . . 120.4(3) ? C20 C21 H21 . . . 118(2) ? C22 C21 H21 . . . 122(2) ? C21 C22 C23 . . . 119.8(4) ? C21 C22 H22 . . . 123(2) ? C23 C22 H22 . . . 117(2) ? C22 C23 C24 . . . 119.6(4) ? C22 C23 H25 . . . 124(2) ? C24 C23 H25 . . . 117(2) ? C19 C24 C23 . . . 121.0(3) ? C19 C24 H24 . . . 121.2(15) ? C23 C24 H24 . . . 117.7(15) ? #-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end