# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_khleb5 _database_code_CSD 185601 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Khlebnikov, Alexander' 'Kopf, Jurgen' 'Kostikov, Rafael R.' 'Novikov, Mikhail S.' 'Voznyi, Igor V.' _publ_contact_author_name 'Prof Alexander Khlebnikov' _publ_contact_author_address ; Department of Chemistry St. Petersburg State University Petrodvorets, Universitetskii pr. 2 St. Petersburg 198504 RUSSIAN FEDERATION ; _publ_contact_author_email 'ALEXANDER.KHLEBNIKOV@POBOX.SPBU.RU' _publ_section_title ; Unprecedented 1,3-Dipolar Cycloaddition of Azomethine Ylides to Ester Carbonyl ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H15 F2 N O2' _chemical_formula_weight 315.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0236(5) _cell_length_b 6.5832(4) _cell_length_c 18.8618(8) _cell_angle_alpha 90.00 _cell_angle_beta 99.721(3) _cell_angle_gamma 90.00 _cell_volume 1471.55(13) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14655 _diffrn_reflns_av_R_equivalents 0.0673 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.45 _reflns_number_total 3343 _reflns_number_gt 2898 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0630P)^2^+0.1960P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3343 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1083 _refine_ls_wR_factor_gt 0.1051 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F501 F 0.44804(6) 0.74568(12) 0.24579(4) 0.02914(19) Uani 1 1 d . . . F502 F 0.27719(6) 0.64844(11) 0.24667(4) 0.02771(19) Uani 1 1 d . . . O501 O 0.25565(6) 0.83472(13) 0.36774(4) 0.02146(19) Uani 1 1 d . . . O502 O 0.38302(6) 1.08011(12) 0.34017(4) 0.02006(19) Uani 1 1 d . . . N501 N 0.30859(8) 0.98844(15) 0.22694(5) 0.0218(2) Uani 1 1 d . . . C501 C 0.07682(9) 0.9653(2) 0.38182(6) 0.0246(3) Uani 1 1 d . . . C502 C 0.30042(9) 1.14712(17) 0.28044(6) 0.0198(2) Uani 1 1 d . . . C503 C 0.34786(9) 0.81118(17) 0.26297(6) 0.0200(2) Uani 1 1 d . . . C504 C 0.10698(10) 1.29620(19) 0.29410(6) 0.0246(3) Uani 1 1 d . . . C505 C 0.17363(9) 0.98250(18) 0.35128(5) 0.0197(2) Uani 1 1 d . . . C506 C 0.18911(9) 1.14625(18) 0.30704(5) 0.0203(2) Uani 1 1 d . . . C507 C 0.28398(10) 0.8475(2) 0.10620(6) 0.0265(3) Uani 1 1 d . . . C508 C 0.24269(11) 0.8651(2) 0.03311(7) 0.0333(3) Uani 1 1 d . . . C509 C 0.36154(9) 0.87233(17) 0.34362(5) 0.0187(2) Uani 1 1 d . . . C510 C 0.00941(10) 1.2806(2) 0.32430(7) 0.0289(3) Uani 1 1 d . . . C511 C 0.53675(11) 0.8614(2) 0.43183(7) 0.0325(3) Uani 1 1 d . . . C512 C 0.43733(11) 0.5346(2) 0.39624(7) 0.0289(3) Uani 1 1 d . . . C513 C 0.20646(11) 1.1763(2) 0.12555(6) 0.0289(3) Uani 1 1 d . . . C514 C -0.00506(10) 1.1159(2) 0.36766(7) 0.0282(3) Uani 1 1 d . . . C515 C 0.45162(9) 0.75998(19) 0.39369(6) 0.0224(2) Uani 1 1 d . . . C516 C 0.26594(9) 1.00424(18) 0.15281(6) 0.0216(2) Uani 1 1 d . . . C517 C 0.16555(12) 1.1906(3) 0.05194(7) 0.0360(3) Uani 1 1 d . . . C518 C 0.18323(11) 1.0357(3) 0.00575(7) 0.0376(3) Uani 1 1 d . . . H501 H -0.0695(13) 1.102(3) 0.3889(8) 0.037(4) Uiso 1 1 d . . . H502 H 0.4911(12) 0.473(3) 0.4364(8) 0.035(4) Uiso 1 1 d . . . H503 H 0.3204(11) 1.277(2) 0.2657(7) 0.018(3) Uiso 1 1 d . . . H504 H 0.2572(13) 0.758(3) 0.0024(9) 0.041(4) Uiso 1 1 d . . . H505 H 0.0699(11) 0.851(2) 0.4131(7) 0.021(3) Uiso 1 1 d . . . H506 H 0.5953(13) 0.792(3) 0.4648(8) 0.037(4) Uiso 1 1 d . . . H507 H 0.1943(13) 1.289(3) 0.1577(8) 0.036(4) Uiso 1 1 d . . . H508 H -0.0448(12) 1.387(2) 0.3153(8) 0.032(4) Uiso 1 1 d . . . H509 H 0.3262(12) 0.728(2) 0.1243(8) 0.027(3) Uiso 1 1 d . . . H510 H 0.1197(11) 1.412(2) 0.2643(7) 0.025(3) Uiso 1 1 d . . . H511 H 0.1267(14) 1.316(3) 0.0337(9) 0.043(4) Uiso 1 1 d . . . H512 H 0.3612(14) 0.494(3) 0.4020(9) 0.043(4) Uiso 1 1 d . . . H513 H 0.4508(13) 0.471(3) 0.3506(9) 0.044(5) Uiso 1 1 d . . . H514 H 0.5418(13) 1.013(3) 0.4278(8) 0.037(4) Uiso 1 1 d . . . H515 H 0.1544(15) 1.043(3) -0.0443(10) 0.054(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F501 0.0290(4) 0.0350(4) 0.0251(3) -0.0009(3) 0.0094(3) 0.0098(3) F502 0.0376(4) 0.0199(4) 0.0241(3) -0.0014(3) 0.0007(3) -0.0058(3) O501 0.0217(4) 0.0214(4) 0.0225(4) 0.0050(3) 0.0071(3) 0.0025(3) O502 0.0226(4) 0.0175(4) 0.0194(4) 0.0003(3) 0.0014(3) -0.0008(3) N501 0.0310(5) 0.0189(5) 0.0156(4) 0.0003(3) 0.0045(4) 0.0020(4) C501 0.0237(5) 0.0290(7) 0.0211(5) -0.0002(5) 0.0041(4) -0.0011(5) C502 0.0253(5) 0.0170(6) 0.0171(5) 0.0010(4) 0.0031(4) -0.0002(4) C503 0.0225(5) 0.0186(6) 0.0194(5) -0.0010(4) 0.0048(4) 0.0002(4) C504 0.0289(6) 0.0217(6) 0.0218(5) -0.0005(4) 0.0000(4) 0.0028(5) C505 0.0212(5) 0.0207(6) 0.0165(5) -0.0023(4) 0.0013(4) 0.0020(4) C506 0.0236(5) 0.0206(6) 0.0161(5) -0.0024(4) 0.0015(4) 0.0001(4) C507 0.0274(6) 0.0315(7) 0.0210(5) -0.0025(5) 0.0048(4) -0.0011(5) C508 0.0337(6) 0.0465(9) 0.0200(6) -0.0075(5) 0.0049(5) -0.0031(6) C509 0.0206(5) 0.0184(6) 0.0176(5) -0.0002(4) 0.0046(4) -0.0001(4) C510 0.0249(6) 0.0300(7) 0.0301(6) -0.0042(5) -0.0001(5) 0.0075(5) C511 0.0279(6) 0.0358(8) 0.0308(6) 0.0030(5) -0.0033(5) 0.0006(5) C512 0.0315(6) 0.0255(7) 0.0280(6) 0.0041(5) 0.0005(5) 0.0053(5) C513 0.0328(6) 0.0338(7) 0.0205(5) 0.0035(5) 0.0060(5) 0.0049(5) C514 0.0213(5) 0.0353(7) 0.0281(6) -0.0049(5) 0.0046(4) 0.0014(5) C515 0.0232(5) 0.0257(6) 0.0187(5) 0.0019(4) 0.0045(4) 0.0047(4) C516 0.0217(5) 0.0269(6) 0.0166(5) 0.0016(4) 0.0048(4) -0.0032(4) C517 0.0354(7) 0.0488(9) 0.0232(6) 0.0094(6) 0.0032(5) 0.0092(6) C518 0.0334(7) 0.0602(10) 0.0181(5) 0.0013(6) 0.0010(5) 0.0011(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F501 C503 1.3687(13) . ? F502 C503 1.3698(13) . ? O501 C505 1.3828(13) . ? O501 C509 1.4439(12) . ? O502 C509 1.3956(14) . ? O502 C502 1.4397(13) . ? N501 C503 1.3921(15) . ? N501 C516 1.4095(13) . ? N501 C502 1.4672(14) . ? C501 C505 1.3878(15) . ? C501 C514 1.3909(17) . ? C501 H505 0.968(14) . ? C502 C506 1.5066(15) . ? C502 H503 0.941(15) . ? C503 C509 1.5553(14) . ? C504 C506 1.3884(16) . ? C504 C510 1.3919(17) . ? C504 H510 0.975(15) . ? C505 C506 1.3949(16) . ? C507 C508 1.3891(16) . ? C507 C516 1.3964(17) . ? C507 H509 0.966(16) . ? C508 C518 1.384(2) . ? C508 H504 0.948(18) . ? C509 C515 1.5056(15) . ? C510 C514 1.386(2) . ? C510 H508 0.953(16) . ? C511 C515 1.3274(18) . ? C511 H506 0.973(16) . ? C511 H514 1.004(18) . ? C512 C515 1.4951(19) . ? C512 H502 0.995(15) . ? C512 H512 0.977(17) . ? C512 H513 0.996(17) . ? C513 C516 1.3908(17) . ? C513 C517 1.3956(17) . ? C513 H507 0.982(17) . ? C514 H501 0.936(16) . ? C517 C518 1.381(2) . ? C517 H511 0.982(17) . ? C518 H515 0.951(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C505 O501 C509 116.23(8) . . ? C509 O502 C502 103.19(8) . . ? C503 N501 C516 125.64(10) . . ? C503 N501 C502 108.52(8) . . ? C516 N501 C502 125.05(9) . . ? C505 C501 C514 118.57(11) . . ? C505 C501 H505 118.7(8) . . ? C514 C501 H505 122.7(8) . . ? O502 C502 N501 101.69(8) . . ? O502 C502 C506 105.81(8) . . ? N501 C502 C506 113.13(9) . . ? O502 C502 H503 109.4(8) . . ? N501 C502 H503 113.1(8) . . ? C506 C502 H503 112.8(8) . . ? F501 C503 F502 103.76(9) . . ? F501 C503 N501 112.84(9) . . ? F502 C503 N501 113.55(9) . . ? F501 C503 C509 111.17(9) . . ? F502 C503 C509 112.40(9) . . ? N501 C503 C509 103.39(9) . . ? C506 C504 C510 119.94(11) . . ? C506 C504 H510 118.8(8) . . ? C510 C504 H510 121.2(8) . . ? O501 C505 C501 117.77(10) . . ? O501 C505 C506 121.06(10) . . ? C501 C505 C506 121.15(10) . . ? C504 C506 C505 119.47(10) . . ? C504 C506 C502 125.74(10) . . ? C505 C506 C502 114.71(10) . . ? C508 C507 C516 119.72(12) . . ? C508 C507 H509 119.8(9) . . ? C516 C507 H509 120.5(9) . . ? C518 C508 C507 120.89(13) . . ? C518 C508 H504 120.9(10) . . ? C507 C508 H504 118.2(10) . . ? O502 C509 O501 111.27(9) . . ? O502 C509 C515 113.05(9) . . ? O501 C509 C515 107.29(8) . . ? O502 C509 C503 101.41(8) . . ? O501 C509 C503 108.10(8) . . ? C515 C509 C503 115.63(9) . . ? C514 C510 C504 119.85(11) . . ? C514 C510 H508 122.0(9) . . ? C504 C510 H508 118.1(9) . . ? C515 C511 H506 121.2(10) . . ? C515 C511 H514 120.6(9) . . ? H506 C511 H514 118.2(13) . . ? C515 C512 H502 111.5(9) . . ? C515 C512 H512 112.9(10) . . ? H502 C512 H512 107.7(13) . . ? C515 C512 H513 110.8(10) . . ? H502 C512 H513 107.8(13) . . ? H512 C512 H513 105.8(14) . . ? C516 C513 C517 119.73(12) . . ? C516 C513 H507 120.3(9) . . ? C517 C513 H507 119.9(9) . . ? C510 C514 C501 121.02(11) . . ? C510 C514 H501 121.7(10) . . ? C501 C514 H501 117.3(10) . . ? C511 C515 C512 124.33(11) . . ? C511 C515 C509 120.00(11) . . ? C512 C515 C509 115.67(10) . . ? C513 C516 C507 119.60(10) . . ? C513 C516 N501 120.34(10) . . ? C507 C516 N501 120.05(11) . . ? C518 C517 C513 120.78(13) . . ? C518 C517 H511 121.0(10) . . ? C513 C517 H511 118.2(10) . . ? C517 C518 C508 119.28(11) . . ? C517 C518 H515 121.5(12) . . ? C508 C518 H515 119.2(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C509 O502 C502 N501 -44.71(10) . . . . ? C509 O502 C502 C506 73.68(10) . . . . ? C503 N501 C502 O502 25.86(11) . . . . ? C516 N501 C502 O502 -163.84(10) . . . . ? C503 N501 C502 C506 -87.15(11) . . . . ? C516 N501 C502 C506 83.15(13) . . . . ? C516 N501 C503 F501 70.47(14) . . . . ? C502 N501 C503 F501 -119.30(10) . . . . ? C516 N501 C503 F502 -47.24(14) . . . . ? C502 N501 C503 F502 122.99(9) . . . . ? C516 N501 C503 C509 -169.32(10) . . . . ? C502 N501 C503 C509 0.91(11) . . . . ? C509 O501 C505 C501 -171.42(9) . . . . ? C509 O501 C505 C506 6.86(14) . . . . ? C514 C501 C505 O501 178.04(10) . . . . ? C514 C501 C505 C506 -0.25(16) . . . . ? C510 C504 C506 C505 -1.01(17) . . . . ? C510 C504 C506 C502 -177.47(10) . . . . ? O501 C505 C506 C504 -177.32(10) . . . . ? C501 C505 C506 C504 0.90(16) . . . . ? O501 C505 C506 C502 -0.49(14) . . . . ? C501 C505 C506 C502 177.74(10) . . . . ? O502 C502 C506 C504 137.15(11) . . . . ? N501 C502 C506 C504 -112.37(12) . . . . ? O502 C502 C506 C505 -39.46(12) . . . . ? N501 C502 C506 C505 71.02(12) . . . . ? C516 C507 C508 C518 -0.3(2) . . . . ? C502 O502 C509 O501 -69.88(10) . . . . ? C502 O502 C509 C515 169.30(8) . . . . ? C502 O502 C509 C503 44.87(9) . . . . ? C505 O501 C509 O502 29.19(12) . . . . ? C505 O501 C509 C515 153.33(9) . . . . ? C505 O501 C509 C503 -81.34(11) . . . . ? F501 C503 C509 O502 93.08(10) . . . . ? F502 C503 C509 O502 -151.10(8) . . . . ? N501 C503 C509 O502 -28.26(10) . . . . ? F501 C503 C509 O501 -149.83(9) . . . . ? F502 C503 C509 O501 -34.02(12) . . . . ? N501 C503 C509 O501 88.83(10) . . . . ? F501 C503 C509 C515 -29.59(13) . . . . ? F502 C503 C509 C515 86.22(11) . . . . ? N501 C503 C509 C515 -150.93(9) . . . . ? C506 C504 C510 C514 0.47(18) . . . . ? C504 C510 C514 C501 0.19(18) . . . . ? C505 C501 C514 C510 -0.30(18) . . . . ? O502 C509 C515 C511 3.56(15) . . . . ? O501 C509 C515 C511 -119.49(12) . . . . ? C503 C509 C515 C511 119.83(12) . . . . ? O502 C509 C515 C512 -176.26(9) . . . . ? O501 C509 C515 C512 60.69(12) . . . . ? C503 C509 C515 C512 -59.99(13) . . . . ? C517 C513 C516 C507 -0.07(18) . . . . ? C517 C513 C516 N501 179.45(12) . . . . ? C508 C507 C516 C513 0.19(18) . . . . ? C508 C507 C516 N501 -179.34(11) . . . . ? C503 N501 C516 C513 165.67(11) . . . . ? C502 N501 C516 C513 -2.99(17) . . . . ? C503 N501 C516 C507 -14.81(17) . . . . ? C502 N501 C516 C507 176.53(10) . . . . ? C516 C513 C517 C518 0.1(2) . . . . ? C513 C517 C518 C508 -0.3(2) . . . . ? C507 C508 C518 C517 0.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.367 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.088