# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/400 data_global _audit_creation_date 2000-01-24 _publ_contact_author_name 'Dr Claude Riche' _publ_contact_author_address ; Institut de Chimie des Substances Naturelles C.N.R.S. 91198 Gif-sur-Yvette CEDEX France ; _publ_contact_letter ; This CIF submission correspond to a paper submitted to PERKIN TRANSACTION I The paper is referenced B000129P/P1P Authors: S. Rigolet, J.-M. Melot, J. Vebrel, A. Chiaroni, C. Riche Title: The reaction of alpha- and omega-Methylactams with nitrones. Influence of electronic and geometric factors on the stereoselectivity of their 1,3 dipolar cycloaddition ; _publ_contact_author_phone ' 1 69 82 30 46' _publ_contact_author_fax ' 1 69 07 72 47' _publ_contact_author_email ' Claude.Riche@icsn.cnrs-gif.fr' data_v113 _audit_creation_method SHELXL #_chemical_absolute_configuration unk??? _chemical_name_systematic ; 3,11-dibenzoyl-6,13dimethyl-7,14-dioxo-2,10-diphenyl-1,9-dioxa- 2,6,10,13-tetraazaspiro[4.2.2.4]tetradecane ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C36 H32 N4 O6' _chemical_formula_weight 616.66 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.932(2) _cell_length_b 9.670(3) _cell_length_c 10.105(2) _cell_angle_alpha 100.95(2) _cell_angle_beta 105.61(2) _cell_angle_gamma 106.37(2) _cell_volume 772.4(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.8 _cell_measurement_theta_max 23.2 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.240 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.060 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method ? _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 0.747 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD4 diffractometer' _diffrn_measurement_method \q/2\q _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2974 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.74 _diffrn_reflns_theta_max 67.89 _reflns_number_total 2797 _reflns_number_gt 2080 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0730P)^2^+0.2025P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2797 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_all 0.1454 _refine_ls_wR_factor_ref 0.1276 _refine_ls_goodness_of_fit_all 1.046 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.046 _refine_ls_restrained_S_obs 1.078 _refine_ls_shift/su_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group C1 C 0.4904(3) 0.3530(2) 0.4323(2) 0.0537(5) Uani 1 d . . N2 N 0.5074(2) 0.4567(2) 0.3607(2) 0.0564(5) Uani 1 d . . C3 C 0.4975(2) 0.6031(2) 0.4112(2) 0.0496(5) Uani 1 d . . O4 O 0.3360(2) 0.6015(2) 0.3347(2) 0.0642(5) Uani 1 d . . N5 N 0.3572(2) 0.6978(2) 0.2393(2) 0.0465(4) Uani 1 d . . C6 C 0.5188(2) 0.8169(2) 0.3175(2) 0.0461(5) Uani 1 d . . H6 H 0.5119(2) 0.8935(2) 0.3923(2) 0.051 Uiso 1 calc R . C7 C 0.6225(3) 0.7290(2) 0.3823(3) 0.0581(6) Uani 1 d . . H7A H 0.7115(3) 0.7927(2) 0.4706(3) 0.064 Uiso 1 calc R . H7B H 0.6700(3) 0.6876(2) 0.3156(3) 0.064 Uiso 1 calc R . C8 C 0.4900(5) 0.4036(3) 0.2088(3) 0.0911(9) Uani 1 d . . H8A H 0.5044(5) 0.4869(3) 0.1689(3) 0.109 Uiso 1 calc R . H8B H 0.3814(5) 0.3293(3) 0.1568(3) 0.109 Uiso 1 calc R . H8C H 0.5727(5) 0.3599(3) 0.2017(3) 0.109 Uiso 1 calc R . O9 O 0.4733(3) 0.2227(2) 0.3787(2) 0.0846(6) Uani 1 d . . C10 C 0.2147(2) 0.7397(2) 0.2051(2) 0.0448(4) Uani 1 d . . C11 C 0.2257(3) 0.8863(2) 0.2069(2) 0.0543(5) Uani 1 d . . H11 H 0.3289(3) 0.9627(2) 0.2391(2) 0.060 Uiso 1 calc R . C12 C 0.0820(3) 0.9177(3) 0.1605(3) 0.0696(7) Uani 1 d . . H12 H 0.0895(3) 1.0156(3) 0.1603(3) 0.077 Uiso 1 calc R . C13 C -0.0715(3) 0.8072(3) 0.1147(3) 0.0745(7) Uani 1 d . . H13 H -0.1673(3) 0.8299(3) 0.0844(3) 0.082 Uiso 1 calc R . C14 C -0.0821(3) 0.6623(3) 0.1143(3) 0.0705(7) Uani 1 d . . H14 H -0.1858(3) 0.5868(3) 0.0834(3) 0.078 Uiso 1 calc R . C15 C 0.0592(3) 0.6282(2) 0.1590(2) 0.0581(5) Uani 1 d . . H15 H 0.0505(3) 0.5299(2) 0.1584(2) 0.064 Uiso 1 calc R . C16 C 0.5856(2) 0.8860(2) 0.2115(2) 0.0477(5) Uani 1 d . . O17 O 0.5331(2) 0.8158(2) 0.0860(2) 0.0720(5) Uani 1 d . . C18 C 0.7184(2) 1.0367(2) 0.2665(2) 0.0472(5) Uani 1 d . . C19 C 0.7616(3) 1.1050(3) 0.1668(3) 0.0661(6) Uani 1 d . . H19 H 0.7047(3) 1.0576(3) 0.0694(3) 0.073 Uiso 1 calc R . C20 C 0.8875(4) 1.2417(3) 0.2103(3) 0.0894(9) Uani 1 d . . H20 H 0.9159(4) 1.2862(3) 0.1423(3) 0.098 Uiso 1 calc R . C21 C 0.9716(4) 1.3132(3) 0.3537(4) 0.0869(9) Uani 1 d . . H21 H 1.0574(4) 1.4056(3) 0.3827(4) 0.096 Uiso 1 calc R . C22 C 0.9296(3) 1.2487(3) 0.4543(3) 0.0779(8) Uani 1 d . . H22 H 0.9862(3) 1.2977(3) 0.5515(3) 0.086 Uiso 1 calc R . C23 C 0.8026(3) 1.1103(2) 0.4113(2) 0.0605(6) Uani 1 d . . H23 H 0.7739(3) 1.0668(2) 0.4796(2) 0.067 Uiso 1 calc R . 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 C1 0.0577(12) 0.0414(10) 0.0589(12) 0.0153(9) 0.0144(10) 0.0179(9) N2 0.0756(12) 0.0519(10) 0.0448(9) 0.0173(8) 0.0155(8) 0.0293(9) C3 0.0484(11) 0.0460(11) 0.0544(11) 0.0233(9) 0.0100(9) 0.0177(9) O4 0.0466(8) 0.0636(9) 0.0848(11) 0.0512(8) 0.0119(7) 0.0135(7) N5 0.0428(9) 0.0421(8) 0.0551(9) 0.0249(7) 0.0126(7) 0.0127(7) C6 0.0421(10) 0.0444(10) 0.0489(10) 0.0206(8) 0.0111(8) 0.0104(8) C7 0.0466(12) 0.0596(13) 0.0707(14) 0.0345(11) 0.0137(10) 0.0184(10) C8 0.133(3) 0.087(2) 0.0534(14) 0.0185(13) 0.030(2) 0.044(2) O9 0.121(2) 0.0434(9) 0.0884(13) 0.0134(8) 0.0404(11) 0.0272(9) C10 0.0454(10) 0.0454(10) 0.0451(10) 0.0191(8) 0.0135(8) 0.0162(8) C11 0.0555(12) 0.0469(11) 0.0598(12) 0.0192(9) 0.0144(10) 0.0197(9) C12 0.079(2) 0.0664(14) 0.073(2) 0.0238(12) 0.0216(13) 0.0424(13) C13 0.0603(15) 0.095(2) 0.077(2) 0.0261(14) 0.0189(12) 0.0432(14) C14 0.0443(12) 0.086(2) 0.078(2) 0.0283(13) 0.0172(11) 0.0176(12) C15 0.0471(11) 0.0549(12) 0.0687(14) 0.0259(10) 0.0156(10) 0.0115(9) C16 0.0475(11) 0.0495(11) 0.0502(11) 0.0213(9) 0.0166(9) 0.0187(9) O17 0.0743(11) 0.0726(11) 0.0500(9) 0.0103(8) 0.0209(8) 0.0028(8) C18 0.0485(11) 0.0447(10) 0.0547(11) 0.0226(9) 0.0206(9) 0.0173(8) C19 0.089(2) 0.0508(12) 0.0647(14) 0.0294(11) 0.0335(12) 0.0191(12) C20 0.127(3) 0.0555(14) 0.093(2) 0.0355(14) 0.059(2) 0.013(2) C21 0.095(2) 0.0513(14) 0.104(2) 0.0197(14) 0.047(2) -0.0004(13) C22 0.075(2) 0.0622(15) 0.072(2) 0.0079(12) 0.0182(13) 0.0014(12) C23 0.0621(13) 0.0587(13) 0.0576(13) 0.0220(10) 0.0230(10) 0.0106(10) _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 C1 O9 1.221(3) . ? C1 N2 1.342(3) . ? C1 C3 1.524(3) 2_666 ? N2 C3 1.447(3) . ? N2 C8 1.474(3) . ? C3 O4 1.436(2) . ? C3 C1 1.524(3) 2_666 ? C3 C7 1.535(3) . ? O4 N5 1.473(2) . ? N5 C10 1.418(2) . ? N5 C6 1.462(2) . ? C6 C7 1.530(3) . ? C6 C16 1.530(3) . ? C10 C15 1.388(3) . ? C10 C11 1.389(3) . ? C11 C12 1.382(3) . ? C12 C13 1.372(4) . ? C13 C14 1.376(4) . ? C14 C15 1.375(3) . ? C16 O17 1.210(2) . ? C16 C18 1.484(3) . ? C18 C19 1.385(3) . ? C18 C23 1.386(3) . ? C19 C20 1.372(4) . ? C20 C21 1.373(4) . ? C21 C22 1.370(4) . ? C22 C23 1.388(3) . ? 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 O9 C1 N2 122.3(2) . . ? O9 C1 C3 117.1(2) . 2_666 ? N2 C1 C3 120.5(2) . 2_666 ? C1 N2 C3 123.2(2) . . ? C1 N2 C8 116.8(2) . . ? C3 N2 C8 117.9(2) . . ? O4 C3 N2 109.0(2) . . ? O4 C3 C1 103.4(2) . 2_666 ? N2 C3 C1 114.7(2) . 2_666 ? O4 C3 C7 106.00(14) . . ? N2 C3 C7 112.8(2) . . ? C1 C3 C7 110.1(2) 2_666 . ? C3 O4 N5 107.52(14) . . ? C10 N5 C6 118.1(2) . . ? C10 N5 O4 106.85(14) . . ? C6 N5 O4 104.74(13) . . ? N5 C6 C7 101.72(15) . . ? N5 C6 C16 109.4(2) . . ? C7 C6 C16 111.1(2) . . ? C6 C7 C3 103.9(2) . . ? C15 C10 C11 119.2(2) . . ? C15 C10 N5 118.5(2) . . ? C11 C10 N5 122.1(2) . . ? C12 C11 C10 119.5(2) . . ? C13 C12 C11 121.2(2) . . ? C12 C13 C14 119.2(2) . . ? C15 C14 C13 120.6(2) . . ? C14 C15 C10 120.3(2) . . ? O17 C16 C18 121.3(2) . . ? O17 C16 C6 119.8(2) . . ? C18 C16 C6 118.9(2) . . ? C19 C18 C23 118.8(2) . . ? C19 C18 C16 117.6(2) . . ? C23 C18 C16 123.5(2) . . ? C20 C19 C18 120.7(2) . . ? C19 C20 C21 120.2(2) . . ? C22 C21 C20 120.2(2) . . ? C21 C22 C23 120.0(3) . . ? C18 C23 C22 120.1(2) . . ? _refine_diff_density_max 0.189 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.053