Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'F. Heaney' _publ_contact_author_address ; Department of Chemistry National University of Ireland Maynooth Co. Kildare REPUBLIC OF IRELAND ; _publ_contact_author_email MARY.F.HEANEY@MAY.IE _publ_section_title ; 1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; first and second generation cycloaddition products ; loop_ _publ_author_name 'F. Heaney' 'Desmond Cunningham' 'E. Lawless' 'Mary Mahon' 'Patrick McArdle' # Attachment 'revised fhm1_1.cif' data_fhm1_1 _database_code_depnum_ccdc_archive 'CCDC 298840' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H20 N2 O5' _chemical_formula_weight 404.41 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5822(15) _cell_length_b 10.3689(13) _cell_length_c 13.0588(9) _cell_angle_alpha 90.275(9) _cell_angle_beta 101.461(11) _cell_angle_gamma 100.074(13) _cell_volume 989.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Marresearch image plate' _diffrn_measurement_method '180 mm image plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3934 _diffrn_reflns_av_R_equivalents 0.0579 _diffrn_reflns_av_sigmaI/netI 0.0813 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 20.86 _reflns_number_total 1920 _reflns_number_gt 1684 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Marresearch MarControl software' _computing_cell_refinement 'XDS (W.Kabsch, 2000)' _computing_data_reduction 'XDS (W.Kabsch, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0571P)^2^+0.2197P] 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 SHELXL _refine_ls_extinction_coef 0.079(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1920 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 O1 O -0.4120(3) 0.86255(19) 0.11811(15) 0.0618(6) Uani 1 1 d . . . O2 O 0.1689(2) 0.80762(17) 0.19941(14) 0.0496(6) Uani 1 1 d . . . O3 O -0.0462(3) 0.98251(19) 0.34211(15) 0.0610(6) Uani 1 1 d . . . O4 O 0.2466(2) 0.96247(17) 0.37649(14) 0.0533(6) Uani 1 1 d . . . O5 O -0.1302(2) 0.95074(17) 0.10197(13) 0.0507(6) Uani 1 1 d . . . N1 N 0.0231(3) 0.5386(2) 0.27794(17) 0.0447(6) Uani 1 1 d . . . N3 N -0.1492(3) 0.6546(2) 0.36797(16) 0.0402(6) Uani 1 1 d . . . C2 C 0.0047(3) 0.6047(2) 0.3584(2) 0.0398(7) Uani 1 1 d . . . C4 C -0.2378(3) 0.7169(2) 0.29769(19) 0.0372(7) Uani 1 1 d . . . C5 C -0.1553(3) 0.7624(2) 0.20175(18) 0.0357(6) Uani 1 1 d . . . C5A C -0.1756(3) 0.6373(2) 0.13580(18) 0.0369(7) Uani 1 1 d . . . C6 C -0.2734(3) 0.6212(3) 0.03338(19) 0.0438(7) Uani 1 1 d . . . H6 H -0.3289 0.6890 0.0035 0.057 Uiso 1 1 calc R . . C7 C -0.2900(4) 0.5077(3) -0.0248(2) 0.0522(8) Uani 1 1 d . . . H7 H -0.3548 0.4999 -0.0936 0.068 Uiso 1 1 calc R . . C8 C -0.2114(4) 0.4055(3) 0.0182(2) 0.0544(8) Uani 1 1 d . . . H8 H -0.2244 0.3280 -0.0209 0.071 Uiso 1 1 calc R . . C9 C -0.1139(4) 0.4185(3) 0.1188(2) 0.0510(7) Uani 1 1 d . . . H9 H -0.0599 0.3494 0.1472 0.066 Uiso 1 1 calc R . . C9A C -0.0935(3) 0.5332(2) 0.18001(19) 0.0400(7) Uani 1 1 d . . . C10 C 0.0465(3) 0.8284(2) 0.23880(19) 0.0360(7) Uani 1 1 d . . . C11 C 0.0771(4) 0.9332(2) 0.32578(19) 0.0402(7) Uani 1 1 d . . . C12 C 0.2840(4) 1.0643(3) 0.4585(2) 0.0696(10) Uani 1 1 d . . . H12A H 0.2309 1.1381 0.4322 0.097 Uiso 1 1 calc R . . H12B H 0.4138 1.0911 0.4812 0.097 Uiso 1 1 calc R . . H12C H 0.2320 1.0310 0.5165 0.097 Uiso 1 1 calc R . . C13 C -0.2519(4) 0.8629(2) 0.13793(19) 0.0415(7) Uani 1 1 d . . . C14 C -0.2018(4) 1.0536(3) 0.0413(2) 0.0654(9) Uani 1 1 d . . . H14A H -0.2909 1.0152 -0.0187 0.092 Uiso 1 1 calc R . . H14B H -0.1037 1.1104 0.0188 0.092 Uiso 1 1 calc R . . H14C H -0.2582 1.1032 0.0836 0.092 Uiso 1 1 calc R . . C15 C 0.1524(3) 0.6158(3) 0.4501(2) 0.0450(7) Uani 1 1 d . . . H15 H 0.2433 0.5669 0.4476 0.058 Uiso 1 1 calc R . . C16 C 0.1706(3) 0.6878(3) 0.5362(2) 0.0447(7) Uani 1 1 d . . . H16 H 0.0739 0.7293 0.5428 0.058 Uiso 1 1 calc R . . C17 C 0.3299(3) 0.7079(2) 0.62242(19) 0.0433(7) Uani 1 1 d . . . C18 C 0.4627(4) 0.6294(3) 0.6342(2) 0.0530(8) Uani 1 1 d . . . H18 H 0.4459 0.5564 0.5893 0.069 Uiso 1 1 calc R . . C19 C 0.6185(4) 0.6573(3) 0.7110(2) 0.0619(9) Uani 1 1 d . . . H19 H 0.7058 0.6034 0.7175 0.081 Uiso 1 1 calc R . . C20 C 0.6454(4) 0.7646(3) 0.7780(2) 0.0636(9) Uani 1 1 d . . . H20 H 0.7516 0.7842 0.8292 0.083 Uiso 1 1 calc R . . C21 C 0.5154(4) 0.8425(3) 0.7691(2) 0.0644(9) Uani 1 1 d . . . H21 H 0.5335 0.9153 0.8143 0.084 Uiso 1 1 calc R . . C22 C 0.3587(4) 0.8138(3) 0.6936(2) 0.0556(8) Uani 1 1 d . . . H22 H 0.2698 0.8660 0.6899 0.072 Uiso 1 1 calc R . . C23 C -0.4218(3) 0.7396(3) 0.3087(2) 0.0503(8) Uani 1 1 d . . . H23A H -0.4476 0.7062 0.3735 0.070 Uiso 1 1 calc R . . H23B H -0.5126 0.6954 0.2516 0.070 Uiso 1 1 calc R . . H23C H -0.4238 0.8319 0.3079 0.070 Uiso 1 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 O1 0.0421(12) 0.0726(15) 0.0721(14) 0.0214(10) 0.0038(10) 0.0224(10) O2 0.0390(11) 0.0560(13) 0.0561(12) -0.0020(9) 0.0118(10) 0.0126(9) O3 0.0511(12) 0.0638(14) 0.0689(14) -0.0168(10) 0.0087(11) 0.0174(11) O4 0.0411(12) 0.0587(13) 0.0545(12) -0.0105(10) 0.0049(10) -0.0002(9) O5 0.0507(11) 0.0500(12) 0.0544(11) 0.0203(9) 0.0100(9) 0.0173(9) N1 0.0441(13) 0.0444(14) 0.0459(15) 0.0047(11) 0.0027(12) 0.0161(10) N3 0.0358(12) 0.0445(13) 0.0393(13) 0.0061(11) 0.0047(11) 0.0075(11) C2 0.0405(16) 0.0365(16) 0.0422(17) 0.0112(13) 0.0053(14) 0.0093(12) C4 0.0330(14) 0.0385(15) 0.0382(15) -0.0012(12) 0.0027(12) 0.0061(12) C5 0.0323(13) 0.0381(15) 0.0376(14) 0.0051(12) 0.0035(11) 0.0127(11) C5A 0.0321(13) 0.0412(16) 0.0378(16) 0.0048(12) 0.0066(12) 0.0086(12) C6 0.0441(15) 0.0468(18) 0.0398(16) 0.0026(13) 0.0045(13) 0.0106(13) C7 0.0515(17) 0.057(2) 0.0421(16) -0.0040(16) 0.0009(13) 0.0046(15) C8 0.0612(18) 0.0437(18) 0.0554(19) -0.0107(15) 0.0093(16) 0.0048(14) C9 0.0557(17) 0.0419(17) 0.0551(19) -0.0014(14) 0.0070(15) 0.0126(13) C9A 0.0383(14) 0.0424(17) 0.0408(16) 0.0041(13) 0.0076(13) 0.0113(12) C10 0.0375(15) 0.0352(15) 0.0383(14) 0.0072(12) 0.0080(13) 0.0146(12) C11 0.0368(17) 0.0424(16) 0.0423(16) 0.0063(13) 0.0080(14) 0.0097(14) C12 0.0634(19) 0.075(2) 0.060(2) -0.0237(18) 0.0071(16) -0.0082(16) C13 0.0415(17) 0.0447(17) 0.0379(15) 0.0014(12) 0.0037(14) 0.0119(14) C14 0.079(2) 0.058(2) 0.0655(19) 0.0278(16) 0.0173(17) 0.0272(16) C15 0.0419(15) 0.0465(17) 0.0472(17) 0.0136(14) 0.0037(14) 0.0157(13) C16 0.0401(15) 0.0508(18) 0.0444(17) 0.0084(14) 0.0058(13) 0.0141(13) C17 0.0428(15) 0.0486(17) 0.0397(15) 0.0116(14) 0.0058(13) 0.0138(13) C18 0.0551(17) 0.0520(18) 0.0499(17) 0.0057(13) -0.0031(15) 0.0199(15) C19 0.0597(19) 0.067(2) 0.0584(19) 0.0077(17) -0.0037(17) 0.0264(16) C20 0.0547(18) 0.082(2) 0.0471(18) 0.0022(17) -0.0090(15) 0.0150(17) C21 0.069(2) 0.078(2) 0.0429(17) -0.0089(15) -0.0008(16) 0.0201(18) C22 0.0556(18) 0.068(2) 0.0466(17) 0.0004(15) 0.0053(16) 0.0268(15) C23 0.0401(15) 0.0609(19) 0.0517(17) 0.0045(14) 0.0109(13) 0.0120(13) _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 O1 C13 1.189(3) . ? O2 C10 1.197(3) . ? O3 C11 1.194(3) . ? O4 C11 1.306(3) . ? O4 C12 1.451(3) . ? O5 C13 1.336(3) . ? O5 C14 1.449(3) . ? N1 C2 1.295(3) . ? N1 C9A 1.398(3) . ? N3 C4 1.274(3) . ? N3 C2 1.384(3) . ? C2 C15 1.457(3) . ? C4 C23 1.488(3) . ? C4 C5 1.548(4) . ? C5 C5A 1.521(3) . ? C5 C13 1.533(3) . ? C5 C10 1.543(3) . ? C5A C6 1.388(3) . ? C5A C9A 1.409(3) . ? C6 C7 1.371(4) . ? C7 C8 1.374(4) . ? C8 C9 1.366(4) . ? C9 C9A 1.398(4) . ? C10 C11 1.523(4) . ? C15 C16 1.317(4) . ? C16 C17 1.462(4) . ? C17 C18 1.388(4) . ? C17 C22 1.394(4) . ? C18 C19 1.375(4) . ? C19 C20 1.373(4) . ? C20 C21 1.368(4) . ? C21 C22 1.371(4) . ? 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 C11 O4 C12 115.8(2) . . ? C13 O5 C14 116.3(2) . . ? C2 N1 C9A 123.5(2) . . ? C4 N3 C2 124.6(2) . . ? N1 C2 N3 125.7(2) . . ? N1 C2 C15 116.6(2) . . ? N3 C2 C15 117.4(2) . . ? N3 C4 C23 118.6(2) . . ? N3 C4 C5 119.5(2) . . ? C23 C4 C5 121.9(2) . . ? C5A C5 C13 110.34(19) . . ? C5A C5 C10 112.35(19) . . ? C13 C5 C10 106.65(19) . . ? C5A C5 C4 104.50(19) . . ? C13 C5 C4 113.7(2) . . ? C10 C5 C4 109.48(19) . . ? C6 C5A C9A 118.4(2) . . ? C6 C5A C5 122.5(2) . . ? C9A C5A C5 119.1(2) . . ? C7 C6 C5A 121.6(2) . . ? C6 C7 C8 120.2(3) . . ? C9 C8 C7 119.5(2) . . ? C8 C9 C9A 121.7(3) . . ? N1 C9A C9 115.9(2) . . ? N1 C9A C5A 125.2(2) . . ? C9 C9A C5A 118.6(2) . . ? O2 C10 C11 121.5(2) . . ? O2 C10 C5 124.3(2) . . ? C11 C10 C5 114.0(2) . . ? O3 C11 O4 125.4(2) . . ? O3 C11 C10 120.9(2) . . ? O4 C11 C10 113.7(2) . . ? O1 C13 O5 123.3(2) . . ? O1 C13 C5 126.5(2) . . ? O5 C13 C5 110.1(2) . . ? C16 C15 C2 126.9(2) . . ? C15 C16 C17 125.6(2) . . ? C18 C17 C22 117.2(2) . . ? C18 C17 C16 122.7(2) . . ? C22 C17 C16 120.0(2) . . ? C19 C18 C17 121.3(3) . . ? C20 C19 C18 120.1(3) . . ? C21 C20 C19 119.8(3) . . ? C20 C21 C22 120.3(3) . . ? C21 C22 C17 121.3(3) . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 20.86 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 0.159 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.042 # Attachment 'alodnitrone MP rearranged - cif file - azomethine ylide' data_fhx _database_code_depnum_ccdc_archive 'CCDC 602119' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H30 N2 O6' _chemical_formula_weight 610.64 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4430(10) _cell_length_b 10.892(2) _cell_length_c 19.212(3) _cell_angle_alpha 82.95(2) _cell_angle_beta 81.14(2) _cell_angle_gamma 88.01(2) _cell_volume 1527.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Marresearch image plate' _diffrn_measurement_method '180 mm image plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7081 _diffrn_reflns_av_R_equivalents 0.0109 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.98 _reflns_number_total 5982 _reflns_number_gt 3370 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Marresearch MarControl software' _computing_cell_refinement 'XDS (W.Kabsch, 2000)' _computing_data_reduction 'XDS (W.Kabsch, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0781P)^2^+0.0000P] 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 5982 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0947 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1417 _refine_ls_wR_factor_gt 0.1190 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 O1 O 0.0812(3) 0.70287(19) 0.19176(10) 0.0769(6) Uani 1 1 d . . . O2 O 0.2374(2) 0.67929(15) 0.08570(9) 0.0573(5) Uani 1 1 d . . . O3 O 0.6212(2) 0.29857(15) 0.32405(8) 0.0536(4) Uani 1 1 d . . . N1 N 0.4854(2) 0.45725(16) 0.26351(9) 0.0368(4) Uani 1 1 d . . . C1 C 0.3340(3) 0.53022(19) 0.25242(11) 0.0391(5) Uani 1 1 d . . . H1 H 0.2384 0.5460 0.2877 0.051 Uiso 1 1 calc R . . C2 C 0.3444(3) 0.57510(19) 0.18360(11) 0.0389(5) Uani 1 1 d . . . C3 C 0.5137(3) 0.53028(18) 0.14676(11) 0.0378(5) Uani 1 1 d . . . C4 C 0.5994(3) 0.5468(2) 0.07678(12) 0.0472(6) Uani 1 1 d . . . H4 H 0.5443 0.5942 0.0421 0.061 Uiso 1 1 calc R . . C5 C 0.7665(4) 0.4919(2) 0.05976(13) 0.0551(7) Uani 1 1 d . . . H5 H 0.8245 0.5018 0.0130 0.072 Uiso 1 1 calc R . . C6 C 0.8503(4) 0.4217(2) 0.11164(13) 0.0559(7) Uani 1 1 d . . . H6 H 0.9641 0.3862 0.0988 0.073 Uiso 1 1 calc R . . C7 C 0.7692(3) 0.4033(2) 0.18150(12) 0.0467(6) Uani 1 1 d . . . H7 H 0.8260 0.3567 0.2160 0.061 Uiso 1 1 calc R . . C8 C 0.5996(3) 0.45729(19) 0.19802(11) 0.0366(5) Uani 1 1 d . . . C9 C 0.5112(3) 0.3832(2) 0.32684(11) 0.0377(5) Uani 1 1 d . . . C10 C 0.4044(3) 0.4156(2) 0.39254(11) 0.0398(5) Uani 1 1 d . . . H10 H 0.3226 0.4821 0.3912 0.052 Uiso 1 1 calc R . . C11 C 0.4235(3) 0.3511(2) 0.45370(11) 0.0394(5) Uani 1 1 d . . . H11 H 0.5045 0.2843 0.4513 0.051 Uiso 1 1 calc R . . C12 C 0.3344(3) 0.3706(2) 0.52454(11) 0.0375(5) Uani 1 1 d . . . C13 C 0.2138(3) 0.4683(2) 0.53705(12) 0.0422(5) Uani 1 1 d . . . H13 H 0.1867 0.5239 0.4992 0.055 Uiso 1 1 calc R . . C14 C 0.1339(3) 0.4832(2) 0.60511(13) 0.0507(6) Uani 1 1 d . . . H14 H 0.0532 0.5490 0.6129 0.066 Uiso 1 1 calc R . . C15 C 0.1722(3) 0.4022(3) 0.66140(13) 0.0545(7) Uani 1 1 d . . . H15 H 0.1181 0.4130 0.7072 0.071 Uiso 1 1 calc R . . C16 C 0.2906(4) 0.3050(3) 0.65001(13) 0.0604(7) Uani 1 1 d . . . H16 H 0.3165 0.2495 0.6881 0.079 Uiso 1 1 calc R . . C17 C 0.3713(3) 0.2894(2) 0.58198(12) 0.0502(6) Uani 1 1 d . . . H17 H 0.4516 0.2234 0.5746 0.065 Uiso 1 1 calc R . . C18 C 0.2053(3) 0.6574(2) 0.15571(13) 0.0470(6) Uani 1 1 d . . . C19 C 0.1116(4) 0.7626(3) 0.05270(16) 0.0762(9) Uani 1 1 d . . . H19A H -0.0087 0.7295 0.0642 0.107 Uiso 1 1 calc R . . H19B H 0.1473 0.7720 0.0022 0.107 Uiso 1 1 calc R . . H19C H 0.1124 0.8418 0.0698 0.107 Uiso 1 1 calc R . . O4 O -0.2137(2) -0.01895(17) 0.08278(9) 0.0600(5) Uani 1 1 d . . . O5 O -0.3723(2) -0.05986(16) 0.19120(9) 0.0573(5) Uani 1 1 d . . . O6 O 0.1325(2) 0.27270(15) 0.32371(8) 0.0502(4) Uani 1 1 d . . . N2 N 0.0087(2) 0.14401(15) 0.26110(8) 0.0353(4) Uani 1 1 d . . . C20 C -0.1347(3) 0.07635(19) 0.24794(11) 0.0372(5) Uani 1 1 d . . . H20 H -0.2340 0.0502 0.2815 0.048 Uiso 1 1 calc R . . C21 C -0.1092(3) 0.05412(19) 0.17951(11) 0.0375(5) Uani 1 1 d . . . C22 C 0.0609(3) 0.10812(19) 0.14584(11) 0.0361(5) Uani 1 1 d . . . C23 C 0.1581(3) 0.1115(2) 0.07749(11) 0.0437(6) Uani 1 1 d . . . H23 H 0.1127 0.0751 0.0426 0.057 Uiso 1 1 calc R . . C24 C 0.3232(4) 0.1702(2) 0.06303(13) 0.0542(7) Uani 1 1 d . . . H24 H 0.3893 0.1742 0.0176 0.070 Uiso 1 1 calc R . . C25 C 0.3922(4) 0.2235(2) 0.11521(13) 0.0569(7) Uani 1 1 d . . . H25 H 0.5047 0.2614 0.1040 0.074 Uiso 1 1 calc R . . C26 C 0.2993(3) 0.2218(2) 0.18282(12) 0.0479(6) Uani 1 1 d . . . H26 H 0.3464 0.2577 0.2175 0.062 Uiso 1 1 calc R . . C27 C 0.1319(3) 0.16414(19) 0.19725(11) 0.0360(5) Uani 1 1 d . . . C28 C 0.0249(3) 0.19146(19) 0.32473(11) 0.0358(5) Uani 1 1 d . . . C29 C -0.0875(3) 0.1360(2) 0.38950(11) 0.0371(5) Uani 1 1 d . . . H29 H -0.1721 0.0764 0.3871 0.048 Uiso 1 1 calc R . . C30 C -0.0686(3) 0.1708(2) 0.45135(11) 0.0375(5) Uani 1 1 d . . . H30 H 0.0140 0.2335 0.4501 0.049 Uiso 1 1 calc R . . C31 C -0.1610(3) 0.12318(19) 0.52139(11) 0.0361(5) Uani 1 1 d . . . C32 C -0.1237(3) 0.1744(2) 0.58051(12) 0.0459(6) Uani 1 1 d . . . H32 H -0.0418 0.2389 0.5743 0.060 Uiso 1 1 calc R . . C33 C -0.2055(4) 0.1314(2) 0.64783(12) 0.0549(7) Uani 1 1 d . . . H33 H -0.1791 0.1669 0.6866 0.071 Uiso 1 1 calc R . . C34 C -0.3265(3) 0.0358(2) 0.65781(12) 0.0517(6) Uani 1 1 d . . . H34 H -0.3821 0.0067 0.7033 0.067 Uiso 1 1 calc R . . C35 C -0.3649(3) -0.0167(2) 0.60019(12) 0.0478(6) Uani 1 1 d . . . H35 H -0.4463 -0.0814 0.6069 0.062 Uiso 1 1 calc R . . C36 C -0.2835(3) 0.0263(2) 0.53279(12) 0.0411(5) Uani 1 1 d . . . H36 H -0.3105 -0.0099 0.4943 0.053 Uiso 1 1 calc R . . C37 C -0.2325(3) -0.0107(2) 0.14484(12) 0.0412(5) Uani 1 1 d . . . C38 C -0.5011(4) -0.1250(3) 0.16070(16) 0.0776(9) Uani 1 1 d . . . H38A H -0.5557 -0.0686 0.1273 0.109 Uiso 1 1 calc R . . H38B H -0.5939 -0.1592 0.1976 0.109 Uiso 1 1 calc R . . H38C H -0.4393 -0.1905 0.1369 0.109 Uiso 1 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 O1 0.0589(12) 0.0973(16) 0.0618(13) 0.0121(11) 0.0059(10) 0.0314(11) O2 0.0689(12) 0.0578(10) 0.0438(10) 0.0009(8) -0.0148(8) 0.0219(9) O3 0.0591(11) 0.0572(10) 0.0416(9) -0.0024(8) -0.0058(8) 0.0207(9) N1 0.0374(10) 0.0384(10) 0.0332(10) -0.0036(7) -0.0020(8) 0.0015(8) C1 0.0366(12) 0.0388(12) 0.0409(13) -0.0043(9) -0.0035(9) 0.0032(10) C2 0.0410(12) 0.0368(12) 0.0375(13) -0.0011(9) -0.0041(10) -0.0013(10) C3 0.0409(12) 0.0314(11) 0.0395(13) -0.0021(9) -0.0023(10) -0.0042(9) C4 0.0557(15) 0.0448(13) 0.0376(13) 0.0029(10) -0.0015(11) -0.0029(11) C5 0.0590(16) 0.0584(15) 0.0396(14) 0.0029(11) 0.0113(12) 0.0000(13) C6 0.0488(15) 0.0587(16) 0.0528(16) -0.0018(12) 0.0098(12) 0.0085(12) C7 0.0432(13) 0.0475(13) 0.0464(14) -0.0012(11) -0.0012(11) 0.0047(11) C8 0.0386(12) 0.0345(11) 0.0351(12) -0.0030(9) -0.0011(9) -0.0034(9) C9 0.0373(12) 0.0410(12) 0.0353(12) -0.0044(9) -0.0075(9) 0.0002(10) C10 0.0369(12) 0.0440(12) 0.0390(13) -0.0065(10) -0.0062(10) 0.0000(10) C11 0.0397(12) 0.0418(12) 0.0379(12) -0.0079(10) -0.0081(10) 0.0015(10) C12 0.0345(11) 0.0436(12) 0.0356(12) -0.0060(9) -0.0075(9) -0.0045(10) C13 0.0372(12) 0.0441(13) 0.0446(13) -0.0041(10) -0.0051(10) -0.0008(10) C14 0.0415(14) 0.0556(15) 0.0540(16) -0.0151(12) 0.0027(11) -0.0004(11) C15 0.0497(15) 0.0771(18) 0.0359(14) -0.0126(12) 0.0020(11) -0.0071(14) C16 0.0652(17) 0.0747(18) 0.0385(14) 0.0043(12) -0.0086(12) 0.0025(15) C17 0.0529(15) 0.0563(15) 0.0392(14) -0.0016(11) -0.0052(11) 0.0099(12) C18 0.0451(14) 0.0442(13) 0.0481(14) 0.0050(11) -0.0044(11) -0.0006(11) C19 0.090(2) 0.0681(19) 0.069(2) 0.0098(15) -0.0275(17) 0.0250(17) O4 0.0613(11) 0.0837(13) 0.0389(10) -0.0217(9) -0.0056(8) -0.0140(10) O5 0.0562(11) 0.0726(12) 0.0458(10) -0.0207(8) -0.0002(8) -0.0249(9) O6 0.0584(11) 0.0524(10) 0.0407(9) -0.0126(7) -0.0009(8) -0.0186(9) N2 0.0381(10) 0.0386(10) 0.0294(9) -0.0072(7) -0.0026(7) -0.0047(8) C20 0.0364(12) 0.0408(12) 0.0344(12) -0.0062(9) -0.0030(9) -0.0042(10) C21 0.0417(13) 0.0393(12) 0.0317(12) -0.0063(9) -0.0048(9) 0.0000(10) C22 0.0420(12) 0.0324(11) 0.0335(12) -0.0039(9) -0.0052(9) 0.0014(9) C23 0.0549(15) 0.0439(13) 0.0309(12) -0.0065(10) 0.0000(10) -0.0008(11) C24 0.0646(17) 0.0552(15) 0.0378(13) -0.0079(11) 0.0117(12) -0.0098(13) C25 0.0539(16) 0.0614(16) 0.0523(16) -0.0126(12) 0.0108(12) -0.0204(13) C26 0.0505(14) 0.0502(14) 0.0422(14) -0.0115(11) 0.0023(11) -0.0121(11) C27 0.0410(12) 0.0348(11) 0.0311(11) -0.0040(9) -0.0022(9) -0.0019(9) C28 0.0386(12) 0.0354(11) 0.0345(12) -0.0071(9) -0.0075(9) 0.0030(10) C29 0.0348(12) 0.0439(12) 0.0334(12) -0.0064(9) -0.0055(9) -0.0012(10) C30 0.0378(12) 0.0405(12) 0.0349(12) -0.0056(9) -0.0072(9) 0.0009(10) C31 0.0335(11) 0.0410(12) 0.0339(12) -0.0058(9) -0.0056(9) 0.0056(10) C32 0.0491(14) 0.0529(14) 0.0373(13) -0.0104(10) -0.0068(10) -0.0034(11) C33 0.0623(16) 0.0701(17) 0.0327(13) -0.0108(11) -0.0054(11) 0.0015(14) C34 0.0502(15) 0.0615(16) 0.0360(13) 0.0051(11) 0.0059(11) 0.0079(13) C35 0.0411(13) 0.0487(14) 0.0496(15) -0.0014(11) 0.0015(11) 0.0027(11) C36 0.0378(12) 0.0482(13) 0.0385(12) -0.0084(10) -0.0072(10) 0.0027(10) C37 0.0434(13) 0.0451(13) 0.0366(13) -0.0130(10) -0.0045(10) 0.0009(10) C38 0.070(2) 0.089(2) 0.080(2) -0.0302(17) -0.0082(16) -0.0366(17) _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 O1 C18 1.198(3) . ? O2 C18 1.323(3) . ? O2 C19 1.444(3) . ? O3 C9 1.213(2) . ? N1 C1 1.385(3) . ? N1 C8 1.406(3) . ? N1 C9 1.410(3) . ? C1 C2 1.344(3) . ? C2 C3 1.447(3) . ? C2 C18 1.467(3) . ? C3 C4 1.390(3) . ? C3 C8 1.406(3) . ? C4 C5 1.372(3) . ? C5 C6 1.392(4) . ? C6 C7 1.378(3) . ? C7 C8 1.382(3) . ? C9 C10 1.460(3) . ? C10 C11 1.318(3) . ? C11 C12 1.456(3) . ? C12 C17 1.383(3) . ? C12 C13 1.387(3) . ? C13 C14 1.377(3) . ? C14 C15 1.369(4) . ? C15 C16 1.370(4) . ? C16 C17 1.379(3) . ? O4 C37 1.193(3) . ? O5 C37 1.341(3) . ? O5 C38 1.445(3) . ? O6 C28 1.210(2) . ? N2 C20 1.389(3) . ? N2 C28 1.408(3) . ? N2 C27 1.413(3) . ? C20 C21 1.350(3) . ? C21 C22 1.440(3) . ? C21 C37 1.460(3) . ? C22 C23 1.395(3) . ? C22 C27 1.399(3) . ? C23 C24 1.379(3) . ? C24 C25 1.388(3) . ? C25 C26 1.373(3) . ? C26 C27 1.388(3) . ? C28 C29 1.464(3) . ? C29 C30 1.320(3) . ? C30 C31 1.457(3) . ? C31 C36 1.393(3) . ? C31 C32 1.394(3) . ? C32 C33 1.375(3) . ? C33 C34 1.377(4) . ? C34 C35 1.378(3) . ? C35 C36 1.376(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 C18 O2 C19 116.4(2) . . ? C1 N1 C8 107.90(17) . . ? C1 N1 C9 126.36(18) . . ? C8 N1 C9 125.29(18) . . ? C2 C1 N1 110.46(19) . . ? C1 C2 C3 107.58(19) . . ? C1 C2 C18 123.1(2) . . ? C3 C2 C18 129.3(2) . . ? C4 C3 C8 119.3(2) . . ? C4 C3 C2 134.1(2) . . ? C8 C3 C2 106.63(18) . . ? C5 C4 C3 118.9(2) . . ? C4 C5 C6 120.8(2) . . ? C7 C6 C5 121.8(2) . . ? C6 C7 C8 117.0(2) . . ? C7 C8 N1 130.4(2) . . ? C7 C8 C3 122.1(2) . . ? N1 C8 C3 107.42(18) . . ? O3 C9 N1 118.90(19) . . ? O3 C9 C10 123.9(2) . . ? N1 C9 C10 117.15(19) . . ? C11 C10 C9 120.3(2) . . ? C10 C11 C12 128.5(2) . . ? C17 C12 C13 118.3(2) . . ? C17 C12 C11 119.1(2) . . ? C13 C12 C11 122.6(2) . . ? C14 C13 C12 120.4(2) . . ? C15 C14 C13 120.5(2) . . ? C14 C15 C16 119.8(2) . . ? C15 C16 C17 119.9(2) . . ? C16 C17 C12 121.0(2) . . ? O1 C18 O2 123.8(2) . . ? O1 C18 C2 124.4(2) . . ? O2 C18 C2 111.7(2) . . ? C37 O5 C38 115.10(19) . . ? C20 N2 C28 126.88(17) . . ? C20 N2 C27 107.56(16) . . ? C28 N2 C27 125.44(17) . . ? C21 C20 N2 110.21(19) . . ? C20 C21 C22 107.68(18) . . ? C20 C21 C37 126.6(2) . . ? C22 C21 C37 125.67(19) . . ? C23 C22 C27 119.7(2) . . ? C23 C22 C21 133.3(2) . . ? C27 C22 C21 107.01(18) . . ? C24 C23 C22 118.3(2) . . ? C23 C24 C25 121.0(2) . . ? C26 C25 C24 121.9(2) . . ? C25 C26 C27 117.2(2) . . ? C26 C27 C22 121.9(2) . . ? C26 C27 N2 130.49(19) . . ? C22 C27 N2 107.52(18) . . ? O6 C28 N2 119.16(19) . . ? O6 C28 C29 123.54(19) . . ? N2 C28 C29 117.27(19) . . ? C30 C29 C28 119.8(2) . . ? C29 C30 C31 128.0(2) . . ? C36 C31 C32 117.7(2) . . ? C36 C31 C30 123.19(19) . . ? C32 C31 C30 119.1(2) . . ? C33 C32 C31 121.2(2) . . ? C32 C33 C34 120.0(2) . . ? C33 C34 C35 119.8(2) . . ? C36 C35 C34 120.3(2) . . ? C35 C36 C31 120.9(2) . . ? O4 C37 O5 123.4(2) . . ? O4 C37 C21 124.8(2) . . ? O5 C37 C21 111.86(18) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.212 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.077 # Attachment 'cif data 1 - ketonitrone DMAD h04pma2' data_c:\x-ray\helix\h04pma2\maxus\h04pma2 _database_code_depnum_ccdc_archive 'CCDC 602120' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N2 O2' _chemical_formula_weight 318.36 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4920(1) _cell_length_b 9.0450(2) _cell_length_c 13.5630(4) _cell_angle_alpha 73.159(1) _cell_angle_beta 73.945(1) _cell_angle_gamma 70.568(1) _cell_volume 812.88(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11569 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 27.485 #_diffrn_measurement_method 'CCD' _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.301 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min 0.9587 _exptl_absorpt_correction_T_max 0.9587 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 KappaCCD _diffrn_measurement_method KappaCCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14444 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 27.57 _reflns_number_total 3688 _reflns_number_gt 3052 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepack (otwinowski & Minor, 1997' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0439P)^2^+0.2083P] 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 SHELXL _refine_ls_extinction_coef 0.043(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3688 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0982 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _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 O1 O 0.81741(12) 0.12635(10) 0.81024(7) 0.0364(2) Uani 1 1 d . . . O2 O 0.68775(12) 0.30997(9) 0.90996(6) 0.0284(2) Uani 1 1 d . . . N1 N 0.28009(13) 0.44105(11) 0.88492(7) 0.0241(2) Uani 1 1 d . . . N2 N 0.32884(13) 0.16263(11) 0.88861(7) 0.0243(2) Uani 1 1 d . . . C1 C 0.30049(15) 0.27919(13) 0.93427(8) 0.0231(2) Uani 1 1 d . . . C2 C 0.39870(16) 0.48384(13) 0.80182(9) 0.0248(2) Uani 1 1 d . . . C3 C 0.57281(16) 0.36415(13) 0.75320(9) 0.0254(2) Uani 1 1 d . . . H3 H 0.6508 0.4256 0.6934 0.031 Uiso 1 1 calc R . . C4 C 0.48883(15) 0.27300(13) 0.70865(9) 0.0246(2) Uani 1 1 d . . . C5 C 0.52312(17) 0.28029(14) 0.60115(9) 0.0298(3) Uani 1 1 d . . . H5 H 0.6028 0.3436 0.5534 0.036 Uiso 1 1 calc R . . C6 C 0.44192(18) 0.19600(15) 0.56340(9) 0.0328(3) Uani 1 1 d . . . H6 H 0.4655 0.2019 0.4900 0.039 Uiso 1 1 calc R . . C7 C 0.32604(18) 0.10287(14) 0.63307(9) 0.0310(3) Uani 1 1 d . . . H7 H 0.2708 0.0447 0.6072 0.037 Uiso 1 1 calc R . . C8 C 0.29077(16) 0.09434(13) 0.73961(9) 0.0271(3) Uani 1 1 d . . . H8 H 0.2130 0.0289 0.7867 0.033 Uiso 1 1 calc R . . C9 C 0.36852(15) 0.18130(12) 0.77914(8) 0.0233(2) Uani 1 1 d . . . C10 C 0.36051(18) 0.65577(14) 0.74386(10) 0.0318(3) Uani 1 1 d . . . H10A H 0.2393 0.7189 0.7798 0.048 Uiso 1 1 calc R . . H10B H 0.3505 0.6634 0.6719 0.048 Uiso 1 1 calc R . . H10C H 0.4668 0.6976 0.7419 0.048 Uiso 1 1 calc R . . C11 C 0.70550(16) 0.25108(13) 0.82745(9) 0.0259(2) Uani 1 1 d . . . C12 C 0.80559(19) 0.20713(15) 0.98601(10) 0.0351(3) Uani 1 1 d . . . H12A H 0.7656 0.1081 1.0175 0.053 Uiso 1 1 calc R . . H12B H 0.7890 0.2633 1.0412 0.053 Uiso 1 1 calc R . . H12C H 0.9417 0.1806 0.9507 0.053 Uiso 1 1 calc R . . C13 C 0.25991(16) 0.24212(13) 1.04924(8) 0.0253(2) Uani 1 1 d . . . H13 H 0.2841 0.1325 1.0851 0.030 Uiso 1 1 calc R . . C14 C 0.19087(16) 0.35401(13) 1.10635(8) 0.0251(2) Uani 1 1 d . . . H14 H 0.1725 0.4626 1.0687 0.030 Uiso 1 1 calc R . . C15 C 0.14030(15) 0.32650(13) 1.22146(8) 0.0244(2) Uani 1 1 d . . . C16 C 0.04231(16) 0.45805(14) 1.26840(9) 0.0271(2) Uani 1 1 d . . . H16 H 0.0141 0.5631 1.2252 0.033 Uiso 1 1 calc R . . C17 C -0.01435(17) 0.43808(15) 1.37674(10) 0.0319(3) Uani 1 1 d . . . H17 H -0.0810 0.5288 1.4072 0.038 Uiso 1 1 calc R . . C18 C 0.02652(18) 0.28530(16) 1.44056(9) 0.0343(3) Uani 1 1 d . . . H18 H -0.0124 0.2709 1.5148 0.041 Uiso 1 1 calc R . . C19 C 0.12475(18) 0.15352(15) 1.39524(9) 0.0335(3) Uani 1 1 d . . . H19 H 0.1532 0.0488 1.4388 0.040 Uiso 1 1 calc R . . C20 C 0.18153(17) 0.17346(14) 1.28713(9) 0.0287(3) Uani 1 1 d . . . H20 H 0.2492 0.0824 1.2572 0.034 Uiso 1 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 O1 0.0312(5) 0.0331(5) 0.0475(5) -0.0159(4) -0.0117(4) -0.0027(4) O2 0.0306(4) 0.0274(4) 0.0295(4) -0.0056(3) -0.0098(3) -0.0082(3) N1 0.0268(5) 0.0225(4) 0.0242(5) -0.0053(4) -0.0062(4) -0.0073(4) N2 0.0262(5) 0.0252(5) 0.0228(5) -0.0062(4) -0.0032(4) -0.0091(4) C1 0.0209(5) 0.0239(5) 0.0250(5) -0.0056(4) -0.0039(4) -0.0070(4) C2 0.0276(6) 0.0243(5) 0.0260(5) -0.0060(4) -0.0080(4) -0.0090(4) C3 0.0255(5) 0.0263(5) 0.0248(5) -0.0044(4) -0.0024(4) -0.0107(4) C4 0.0228(5) 0.0245(5) 0.0253(5) -0.0069(4) -0.0044(4) -0.0039(4) C5 0.0279(6) 0.0328(6) 0.0247(6) -0.0062(5) -0.0015(4) -0.0065(5) C6 0.0361(6) 0.0369(6) 0.0236(6) -0.0108(5) -0.0063(5) -0.0039(5) C7 0.0346(6) 0.0307(6) 0.0311(6) -0.0124(5) -0.0108(5) -0.0051(5) C8 0.0279(6) 0.0248(5) 0.0296(6) -0.0079(4) -0.0059(4) -0.0068(4) C9 0.0236(5) 0.0219(5) 0.0235(5) -0.0063(4) -0.0049(4) -0.0038(4) C10 0.0361(6) 0.0251(6) 0.0334(6) -0.0012(5) -0.0082(5) -0.0109(5) C11 0.0230(5) 0.0268(6) 0.0306(6) -0.0073(4) -0.0028(4) -0.0112(4) C12 0.0409(7) 0.0324(6) 0.0350(7) -0.0017(5) -0.0170(5) -0.0109(5) C13 0.0280(6) 0.0236(5) 0.0244(6) -0.0044(4) -0.0043(4) -0.0085(4) C14 0.0247(5) 0.0251(5) 0.0261(6) -0.0056(4) -0.0039(4) -0.0086(4) C15 0.0218(5) 0.0283(6) 0.0261(6) -0.0099(4) -0.0043(4) -0.0078(4) C16 0.0241(5) 0.0279(6) 0.0316(6) -0.0102(5) -0.0061(4) -0.0066(4) C17 0.0264(6) 0.0383(7) 0.0337(6) -0.0188(5) -0.0044(5) -0.0044(5) C18 0.0310(6) 0.0481(7) 0.0234(6) -0.0126(5) -0.0036(5) -0.0080(5) C19 0.0350(6) 0.0347(6) 0.0273(6) -0.0044(5) -0.0080(5) -0.0055(5) C20 0.0293(6) 0.0287(6) 0.0276(6) -0.0096(5) -0.0050(5) -0.0049(5) _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 O1 C11 1.2022(14) . ? O2 C11 1.3302(14) . ? O2 C12 1.4526(14) . ? N1 C2 1.2775(14) . ? N1 C1 1.3980(13) . ? N2 C1 1.3026(14) . ? N2 C9 1.4020(14) . ? C1 C13 1.4625(15) . ? C2 C10 1.4961(15) . ? C2 C3 1.5188(16) . ? C3 C4 1.5115(15) . ? C3 C11 1.5261(16) . ? C4 C5 1.3945(16) . ? C4 C9 1.4056(15) . ? C5 C6 1.3859(18) . ? C6 C7 1.3884(18) . ? C7 C8 1.3789(16) . ? C8 C9 1.4026(15) . ? C13 C14 1.3327(16) . ? C14 C15 1.4674(15) . ? C15 C20 1.3993(16) . ? C15 C16 1.3997(16) . ? C16 C17 1.3872(16) . ? C17 C18 1.3873(18) . ? C18 C19 1.3894(18) . ? C19 C20 1.3844(16) . ? 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 C11 O2 C12 115.50(9) . . ? C2 N1 C1 121.32(9) . . ? C1 N2 C9 123.10(9) . . ? N2 C1 N1 126.21(10) . . ? N2 C1 C13 117.04(9) . . ? N1 C1 C13 116.19(9) . . ? N1 C2 C10 120.04(10) . . ? N1 C2 C3 122.49(10) . . ? C10 C2 C3 117.31(10) . . ? C4 C3 C2 104.71(9) . . ? C4 C3 C11 111.68(9) . . ? C2 C3 C11 115.54(9) . . ? C5 C4 C9 119.69(10) . . ? C5 C4 C3 122.36(10) . . ? C9 C4 C3 117.93(9) . . ? C6 C5 C4 120.56(11) . . ? C5 C6 C7 119.84(11) . . ? C8 C7 C6 120.31(11) . . ? C7 C8 C9 120.68(11) . . ? N2 C9 C8 116.80(9) . . ? N2 C9 C4 124.21(10) . . ? C8 C9 C4 118.88(10) . . ? O1 C11 O2 124.64(11) . . ? O1 C11 C3 123.15(10) . . ? O2 C11 C3 112.16(9) . . ? C14 C13 C1 123.47(10) . . ? C13 C14 C15 126.61(10) . . ? C20 C15 C16 118.06(10) . . ? C20 C15 C14 122.94(10) . . ? C16 C15 C14 118.99(10) . . ? C17 C16 C15 121.29(11) . . ? C18 C17 C16 119.84(11) . . ? C17 C18 C19 119.60(11) . . ? C20 C19 C18 120.57(11) . . ? C19 C20 C15 120.65(11) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.226 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.035