# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Veronique Blandin' _publ_contact_author_email VERONIQUE.BLANDIN@UJF-GRENOBLE.FR _publ_section_title ; MiPNO, a new chiral cyclic nitrone for enantioselective amino acid synthesis: the cycloaddition approach. ; loop_ _publ_author_footnote ; FIRST AUTHORS FOOTNOTES ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? loop_ _publ_author_name 'Veronique Blandin' 'Pierre Y Chavant' 'Christian Philouze' 'Maryse Thiverny' # -- ENTER TORSION ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 C4 52.8(1) . . . . yes #------------------------------------------------------------------------------ # Attachment 'Blandin_compound_1_final.cif' data_Enregistrement2 _database_code_depnum_ccdc_archive 'CCDC 747517' #TrackingRef 'Blandin_compound_1_final.cif' _computing_data_collection 'Bruker-Enraf-Nonius kappaCCD' _computing_cell_refinement 'Bruker-Enraf-Nonius kappaCCD' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 6.900(2) _cell_length_b 7.365(2) _cell_length_c 8.819(2) _cell_angle_alpha 83.78(2) _cell_angle_beta 86.06(2) _cell_angle_gamma 84.78(2) _cell_volume 442.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293.0 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0.0 _cell_measurement_theta_max 0.0 #------------------------------------------------------------------------------ _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.276 #_exptl_crystal_density_meas 'not measured' _chemical_formula_weight 170.21 _chemical_formula_analytical ? _chemical_formula_sum 'C8 H14 N2 O2 ' _chemical_formula_moiety 'C8 H14 N2 O2 ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 184.00 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293.0 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector CCD _diffrn_measurement_device_type 'Bruker-Enraf-Nonius kappaCCD' _diffrn_detector_area_resol_mean ? _diffrn_measurement_method 'phi scans and omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.00 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? _diffrn_reflns_number 9127 _reflns_number_total 2392 _reflns_number_gt 1930 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.09075 _diffrn_reflns_av_sigmaI/netI 0.040 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 29.97 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 16 0.002 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 28 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 4 0.004 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 4 0.008 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(10) 0.1072(2) 0.2378(2) 0.5055(1) 0.0536(3) 1.000 . Uani d ? O(11) 0.1938(1) -0.1506(1) 0.9496(1) 0.0416(2) 1.000 . Uani d ? N(1) 0.1455(1) 0.1675(1) 0.6390(1) 0.0333(2) 1.000 . Uani d ? N(3) 0.2516(1) 0.1494(1) 0.8781(1) 0.0267(2) 1.000 . Uani d ? C(2) 0.2222(1) 0.2845(1) 0.7473(1) 0.0248(2) 1.000 . Uani d ? C(4) 0.1932(2) -0.0155(2) 0.8562(1) 0.0291(2) 1.000 . Uani d ? C(5) 0.1303(2) 0.0014(2) 0.7004(1) 0.0356(3) 1.000 . Uani d ? C(6) 0.2921(2) 0.1949(2) 1.0281(1) 0.0369(3) 1.000 . Uani d ? C(7) 0.4103(2) 0.3587(2) 0.6707(1) 0.0295(2) 1.000 . Uani d ? C(8) 0.5624(2) 0.2079(2) 0.6302(2) 0.0563(4) 1.000 . Uani d ? C(8') 0.4977(2) 0.4886(2) 0.7634(2) 0.0473(3) 1.000 . Uani d ? C(9) 0.0616(2) 0.4334(2) 0.7786(2) 0.0382(3) 1.000 . Uani d ? H(1) 0.0852 -0.0944 0.6518 0.043 1.000 . Uiso c ? H(2) 0.2212 0.3075 1.0477 0.044 1.000 . Uiso c ? H(3) 0.4277 0.2065 1.0315 0.044 1.000 . Uiso c ? H(4) 0.2540 0.1005 1.1034 0.044 1.000 . Uiso c ? H(5) 0.3760 0.4270 0.5774 0.035 1.000 . Uiso c ? H(6) 0.6741 0.2605 0.5811 0.068 1.000 . Uiso c ? H(7) 0.5983 0.1340 0.7206 0.068 1.000 . Uiso c ? H(8) 0.5106 0.1345 0.5632 0.068 1.000 . Uiso c ? H(9) 0.5534 0.4215 0.8502 0.057 1.000 . Uiso c ? H(10) 0.5960 0.5493 0.7022 0.057 1.000 . Uiso c ? H(11) 0.3987 0.5767 0.7958 0.057 1.000 . Uiso c ? H(12) 0.1010 0.5051 0.8525 0.046 1.000 . Uiso c ? H(13) 0.0375 0.5095 0.6867 0.046 1.000 . Uiso c ? H(14) -0.0540 0.3785 0.8163 0.046 1.000 . Uiso c ? 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(10) 0.0809(6) 0.0524(6) 0.0327(4) -0.0235(5) -0.0289(4) 0.0039(4) O(11) 0.0448(4) 0.0332(4) 0.0444(5) -0.0052(4) -0.0027(4) 0.0080(4) N(1) 0.0429(5) 0.0330(4) 0.0271(4) -0.0119(4) -0.0122(4) -0.0033(4) N(3) 0.0311(4) 0.0291(4) 0.0208(4) -0.0036(3) -0.0046(3) -0.0035(3) C(2) 0.0283(4) 0.0250(4) 0.0225(4) -0.0050(3) -0.0057(3) -0.0039(4) C(4) 0.0278(4) 0.0289(5) 0.0305(5) -0.0027(4) -0.0015(4) -0.0029(4) C(5) 0.0445(6) 0.0315(5) 0.0338(5) -0.0110(4) -0.0077(4) -0.0065(4) C(6) 0.0409(5) 0.0476(6) 0.0239(5) -0.0046(5) -0.0087(4) -0.0058(5) C(7) 0.0336(5) 0.0303(5) 0.0261(5) -0.0080(4) -0.0006(4) -0.0052(4) C(8) 0.0463(7) 0.0472(7) 0.074(1) -0.0056(6) 0.0241(7) -0.0178(7) C(8') 0.0436(6) 0.0542(7) 0.0497(7) -0.0221(5) 0.0027(5) -0.0193(6) C(9) 0.0329(5) 0.0327(5) 0.0474(7) 0.0031(4) -0.0033(5) -0.0011(5) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00090|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1930 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_all 0.0867 _refine_ls_wR_factor_ref 0.0867 _refine_ls_goodness_of_fit_all 1.935 _refine_ls_goodness_of_fit_ref 1.935 _refine_ls_shift/su_max 0.0040 _refine_ls_shift/su_mean 0.0010 _refine_diff_density_min -0.28 _refine_diff_density_max 0.35 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O10 N1 1.269(1) . . yes O11 C4 1.221(1) . . yes N1 C2 1.505(1) . . yes N1 C5 1.293(2) . . yes N3 C2 1.452(1) . . yes N3 C4 1.350(2) . . yes N3 C6 1.451(1) . . yes C2 C7 1.539(2) . . yes C2 C9 1.519(2) . . yes C4 C5 1.458(2) . . yes C5 H1 0.95 . . no C6 H2 0.95 . . no C6 H3 0.95 . . no C6 H4 0.95 . . no C7 C8 1.512(2) . . yes C7 C8' 1.513(2) . . yes C7 H5 0.95 . . no C8 H6 0.95 . . no C8 H7 0.95 . . no C8 H8 0.95 . . no C8' H9 0.95 . . no C8' H10 0.95 . . no C8' H11 0.95 . . no C9 H12 0.95 . . no C9 H13 0.95 . . no C9 H14 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O10 N1 C2 119.12(9) . . . yes O10 N1 C5 129.1(1) . . . yes C2 N1 C5 111.80(9) . . . yes C2 N3 C4 112.57(9) . . . yes C2 N3 C6 123.7(1) . . . yes C4 N3 C6 122.0(1) . . . yes N1 C2 N3 99.97(8) . . . yes N1 C2 C7 107.45(8) . . . yes N1 C2 C9 106.91(9) . . . yes N3 C2 C7 114.64(8) . . . yes N3 C2 C9 112.76(9) . . . yes C7 C2 C9 113.71(9) . . . yes O11 C4 N3 126.2(1) . . . yes O11 C4 C5 127.5(1) . . . yes N3 C4 C5 106.4(1) . . . yes N1 C5 C4 109.2(1) . . . yes N1 C5 H1 125.4 . . . no C4 C5 H1 125.4 . . . no N3 C6 H2 109.5 . . . no N3 C6 H3 109.5 . . . no N3 C6 H4 109.5 . . . no H2 C6 H3 109.5 . . . no H2 C6 H4 109.5 . . . no H3 C6 H4 109.5 . . . no C2 C7 C8 112.7(1) . . . yes C2 C7 C8' 113.27(9) . . . yes C2 C7 H5 106.8 . . . no C8 C7 C8' 110.0(1) . . . yes C8 C7 H5 106.8 . . . no C8' C7 H5 106.8 . . . no C7 C8 H6 109.5 . . . no C7 C8 H7 109.5 . . . no C7 C8 H8 109.5 . . . no H6 C8 H7 109.5 . . . no H6 C8 H8 109.5 . . . no H7 C8 H8 109.5 . . . no C7 C8' H9 109.5 . . . no C7 C8' H10 109.5 . . . no C7 C8' H11 109.5 . . . no H9 C8' H10 109.5 . . . no H9 C8' H11 109.5 . . . no H10 C8' H11 109.5 . . . no C2 C9 H12 109.5 . . . no C2 C9 H13 109.5 . . . no C2 C9 H14 109.5 . . . no H12 C9 H13 109.5 . . . no H12 C9 H14 109.5 . . . no H13 C9 H14 109.5 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O10 C5 3.273(2) . 2_556 no O10 C9 3.475(2) . 2_566 no O11 C4 3.285(1) . 2_557 no O11 N3 3.333(1) . 2_557 no O11 C6 3.388(2) . 2_557 no O11 O11 3.447(2) . 2_557 no O11 C9 3.492(2) . 2_557 no O11 C6 3.550(2) . 2_657 no C4 C4 3.561(2) . 2_557 no C6 C8' 3.581(2) . 2_667 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag ? ? ? ? ? ? ? ? ? ? # -- ENTER TORSION ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 C4 52.8(1) . . . . yes #------------------------------------------------------------------------------ # Attachment 'Blandin_compound_10a_final.cif' data_THIVERN _database_code_depnum_ccdc_archive 'CCDC 747518' _audit_creation_date 2009-07-24 _audit_creation_method 'by teXsan v1.8' _audit_update_record ; ? ; _publ_section_title_footnote ' ENTER ANY FOOTNOTES TO TITLE ' _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; #------------------------------------------------------------------------------ _computing_data_collection 'Bruker-Enraf-Nonius CAD4' _computing_cell_refinement 'Bruker-Enraf-Nonius CAD4' _computing_data_reduction 'teXsan (MSC, 1992-1997)' _computing_structure_solution SIR92 _computing_structure_refinement 'teXsan (MSC, 1992-1997)' _computing_publication_material 'teXsan (MSC, 1992-1997)' #------------------------------------------------------------------------------ _cell_length_a 10.080(3) _cell_length_b 9.129(4) _cell_length_c 11.610(3) _cell_angle_alpha 90 _cell_angle_beta 112.49(3) _cell_angle_gamma 90 _cell_volume 987.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293.0 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 20.27 _cell_measurement_theta_max 24.90 #------------------------------------------------------------------------------ _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_Int_Tables_number 4 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y, -z' #------------------------------------------------------------------------------ _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.23 _exptl_crystal_density_diffrn 1.270 #_exptl_crystal_density_meas 'not measured' _chemical_formula_weight 377.44 _chemical_formula_analytical ? _chemical_formula_sum 'C19 H27 N3 O5 ' _chemical_formula_moiety 'C19 H27 N3 O5 ' _chemical_formula_structural ? _chemical_compound_source ? _chemical_absolute_configuration syn _exptl_crystal_F_000 404.00 _exptl_absorpt_coefficient_mu 0.764 _exptl_absorpt_correction_type none _exptl_special_details ; absolute configuration of atom C11 was known from the configuration of the starting material ( (S) phenylalanin ). ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293.0 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device_type CAD-4 _diffrn_measurement_method 'omega scans' _diffrn_standards_number 2 _diffrn_standards_interval_count 120 _diffrn_standards_decay_% -3.76 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -2 1 6 -2 -1 6 _diffrn_reflns_number 2273 _reflns_number_total 2174 _reflns_number_gt 2064 _reflns_threshold_expression I>2.00\s(I) _diffrn_reflns_av_R_equivalents 0.07243 _diffrn_reflns_av_sigmaI/netI 0.010 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.12 _diffrn_reflns_theta_max 74.88 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.04778 _diffrn_orient_matrix_UB_12 0.01284 _diffrn_orient_matrix_UB_13 0.09236 _diffrn_orient_matrix_UB_21 0.07269 _diffrn_orient_matrix_UB_22 0.06628 _diffrn_orient_matrix_UB_23 -0.01193 _diffrn_orient_matrix_UB_31 -0.06298 _diffrn_orient_matrix_UB_32 0.08625 _diffrn_orient_matrix_UB_33 -0.00460 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 38 0.017 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 54 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N 0 6 0.029 0.018 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O 0 10 0.047 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(22) -0.4084(1) -0.2184(2) -0.3534(1) 0.0558(3) 1.000 . Uani d ? O(23) -0.4063(1) -0.4493(2) -0.4233(1) 0.0551(3) 1.000 . Uani d ? O(24) -0.2737(1) -0.3012(2) -0.6408(1) 0.0645(3) 1.000 . Uani d ? O(25) -0.3906(1) -0.5082(1) -0.73576(9) 0.0432(2) 1.000 . Uani d ? O(26) -0.4542(2) -0.8386(2) -0.9615(1) 0.0710(4) 1.000 . Uani d ? N(1) -0.2670(1) -0.5449(2) -0.7672(1) 0.0420(2) 1.000 . Uani d ? N(4) -0.2905(1) -0.7986(2) -0.7640(1) 0.0458(3) 1.000 . Uani d ? N(12) -0.5009(1) -0.2589(2) -0.5569(1) 0.0468(3) 1.000 . Uani d ? C(2) -0.3381(2) -0.6018(2) -0.8963(1) 0.0481(3) 1.000 . Uani d ? C(3) -0.3701(2) -0.7596(2) -0.8813(1) 0.0476(3) 1.000 . Uani d ? C(5) -0.1979(1) -0.6773(2) -0.6934(1) 0.0415(3) 1.000 . Uani d ? C(6) -0.3012(2) -0.9438(2) -0.7157(2) 0.0613(4) 1.000 . Uani d ? C(7) -0.0468(2) -0.6839(2) -0.7002(2) 0.0519(3) 1.000 . Uani d ? C(8) 0.0514(2) -0.5644(3) -0.6230(2) 0.0688(5) 1.000 . Uani d ? C(8') 0.0232(2) -0.8336(3) -0.6646(3) 0.0770(6) 1.000 . Uani d ? C(9) -0.1918(2) -0.6715(2) -0.5613(1) 0.0533(3) 1.000 . Uani d ? C(10) -0.3784(1) -0.3777(2) -0.6776(1) 0.0442(3) 1.000 . Uani d ? C(11) -0.5222(2) -0.3438(2) -0.6680(1) 0.0438(3) 1.000 . Uani d ? C(13) -0.4369(1) -0.3191(2) -0.4433(1) 0.0418(3) 1.000 . Uani d ? C(14) -0.3391(2) -0.2657(3) -0.2272(2) 0.0634(4) 1.000 . Uani d ? C(15) -0.6143(2) -0.2576(2) -0.7863(1) 0.0495(3) 1.000 . Uani d ? C(16) -0.7736(2) -0.2771(2) -0.8244(1) 0.0483(3) 1.000 . Uani d ? C(17) -0.8479(2) -0.3748(3) -0.9197(2) 0.0662(4) 1.000 . Uani d ? C(18) -0.9943(3) -0.3939(4) -0.9564(2) 0.0801(6) 1.000 . Uani d ? C(19) -1.0699(2) -0.3171(3) -0.9008(2) 0.0743(5) 1.000 . Uani d ? C(20) -0.9989(2) -0.2210(3) -0.8064(2) 0.0704(5) 1.000 . Uani d ? C(21) -0.8513(2) -0.1999(2) -0.7693(2) 0.0562(4) 1.000 . Uani d ? H(1) -0.2757 -0.5939 -0.9401 0.058 1.000 . Uiso c ? H(2) -0.4242 -0.5495 -0.9400 0.058 1.000 . Uiso c ? H(3) -0.3383 -0.9353 -0.6521 0.074 1.000 . Uiso c ? H(4) -0.2087 -0.9876 -0.6822 0.074 1.000 . Uiso c ? H(5) -0.3636 -1.0031 -0.7813 0.074 1.000 . Uiso c ? H(6) -0.0600 -0.6668 -0.7846 0.062 1.000 . Uiso c ? H(7) 0.0839 -0.5894 -0.5371 0.083 1.000 . Uiso c ? H(8) 0.0004 -0.4744 -0.6369 0.083 1.000 . Uiso c ? H(9) 0.1315 -0.5546 -0.6464 0.083 1.000 . Uiso c ? H(10) 0.0324 -0.8572 -0.5822 0.092 1.000 . Uiso c ? H(11) 0.1156 -0.8318 -0.6686 0.092 1.000 . Uiso c ? H(12) -0.0346 -0.9053 -0.7208 0.092 1.000 . Uiso c ? H(13) -0.1368 -0.7517 -0.5152 0.064 1.000 . Uiso c ? H(14) -0.1484 -0.5823 -0.5234 0.064 1.000 . Uiso c ? H(15) -0.2865 -0.6770 -0.5625 0.064 1.000 . Uiso c ? H(16) -0.5693 -0.4330 -0.6650 0.053 1.000 . Uiso c ? H(17) -0.5325 -0.1600 -0.5644 0.056 1.000 . Uiso c ? H(18) -0.4023 -0.2531 -0.1848 0.076 1.000 . Uiso c ? H(19) -0.2547 -0.2092 -0.1872 0.076 1.000 . Uiso c ? H(20) -0.3141 -0.3662 -0.2257 0.076 1.000 . Uiso c ? H(21) -0.5927 -0.1564 -0.7711 0.059 1.000 . Uiso c ? H(22) -0.5891 -0.2893 -0.8532 0.059 1.000 . Uiso c ? H(23) -0.7973 -0.4288 -0.9599 0.079 1.000 . Uiso c ? H(24) -1.0430 -0.4613 -1.0211 0.096 1.000 . Uiso c ? H(25) -1.1708 -0.3301 -0.9273 0.089 1.000 . Uiso c ? H(26) -1.0505 -0.1686 -0.7662 0.084 1.000 . Uiso c ? H(27) -0.8036 -0.1314 -0.7051 0.067 1.000 . Uiso c ? 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(22) 0.0700(6) 0.0460(6) 0.0445(4) 0.0097(5) 0.0141(4) -0.0038(5) O(23) 0.0676(6) 0.0344(5) 0.0548(5) 0.0019(5) 0.0140(5) 0.0037(5) O(24) 0.0540(5) 0.0452(7) 0.0914(8) -0.0098(5) 0.0245(5) -0.0228(6) O(25) 0.0460(4) 0.0337(5) 0.0503(4) 0.0007(4) 0.0189(3) -0.0055(4) O(26) 0.0800(7) 0.0702(8) 0.0558(5) -0.0278(7) 0.0181(5) -0.0232(6) N(1) 0.0438(4) 0.0349(6) 0.0468(5) 0.0017(4) 0.0167(4) -0.0032(4) N(4) 0.0499(5) 0.0331(6) 0.0511(5) -0.0024(5) 0.0157(4) -0.0018(5) N(12) 0.0587(6) 0.0352(6) 0.0435(5) 0.0128(5) 0.0160(4) 0.0004(4) C(2) 0.0561(6) 0.0451(8) 0.0403(5) 0.0031(6) 0.0154(5) -0.0012(6) C(3) 0.0519(6) 0.0453(7) 0.0460(5) -0.0038(6) 0.0193(4) -0.0079(5) C(5) 0.0470(5) 0.0326(6) 0.0435(5) 0.0043(5) 0.0157(4) -0.0009(5) C(6) 0.0641(8) 0.0382(8) 0.079(1) -0.0042(7) 0.0244(7) 0.0071(7) C(7) 0.0438(6) 0.0503(8) 0.0591(6) 0.0040(6) 0.0168(5) -0.0006(7) C(8) 0.0550(7) 0.063(1) 0.078(1) -0.0108(9) 0.0137(7) -0.006(1) C(8') 0.0561(8) 0.059(1) 0.114(2) 0.0131(9) 0.0299(9) 0.001(1) C(9) 0.0598(7) 0.0531(8) 0.0431(5) 0.0031(7) 0.0153(5) -0.0003(6) C(10) 0.0463(5) 0.0324(6) 0.0487(5) 0.0016(5) 0.0126(4) -0.0017(5) C(11) 0.0487(5) 0.0329(6) 0.0458(5) 0.0046(6) 0.0138(4) 0.0019(5) C(13) 0.0435(5) 0.0357(6) 0.0449(5) 0.0050(5) 0.0153(4) 0.0000(5) C(14) 0.0683(9) 0.067(1) 0.0471(6) 0.005(1) 0.0133(6) -0.0009(8) C(15) 0.0511(6) 0.0475(8) 0.0472(6) 0.0063(6) 0.0158(5) 0.0060(6) C(16) 0.0490(6) 0.0440(7) 0.0449(6) 0.0055(6) 0.0102(5) 0.0064(6) C(17) 0.0693(8) 0.064(1) 0.0571(7) 0.0007(9) 0.0144(6) -0.0130(8) C(18) 0.0696(9) 0.081(1) 0.069(1) -0.017(1) 0.0034(8) -0.016(1) C(19) 0.0523(7) 0.072(1) 0.085(1) -0.0100(9) 0.0107(7) 0.0153(9) C(20) 0.0584(7) 0.059(1) 0.097(1) 0.0053(8) 0.0329(7) 0.003(1) C(21) 0.0557(6) 0.0482(9) 0.0616(7) 0.0039(7) 0.0190(6) -0.0039(7) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[\s^2^(Fo) + 0.00226|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method 'Zachariasen (1967)' _refine_ls_extinction_coef 0.00014(1) _refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.' _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2064 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_all 0.0921 _refine_ls_wR_factor_ref 0.0921 _refine_ls_goodness_of_fit_all 1.948 _refine_ls_goodness_of_fit_ref 1.948 _refine_ls_shift/su_max 0.0783 _refine_ls_shift/su_mean 0.0630 _refine_diff_density_min -0.22 _refine_diff_density_max 0.21 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O22 C13 1.337(3) . . yes O22 C14 1.428(3) . . yes O23 C13 1.227(3) . . yes O24 C10 1.200(3) . . yes O25 N1 1.464(2) . . yes O25 C10 1.352(2) . . yes O26 C3 1.226(3) . . yes N1 C2 1.487(2) . . yes N1 C5 1.491(3) . . yes N4 C3 1.337(3) . . yes N4 C5 1.477(2) . . yes N4 C6 1.460(3) . . yes N12 C11 1.449(3) . . yes N12 C13 1.344(2) . . yes N12 H17 0.95 . . no C2 C3 1.501(4) . . yes C2 H1 0.95 . . no C2 H2 0.95 . . no C5 C7 1.557(3) . . yes C5 C9 1.511(3) . . yes C6 H3 0.95 . . no C6 H4 0.95 . . no C6 H5 0.95 . . no C7 C8 1.515(4) . . yes C7 C8' 1.521(4) . . yes C7 H6 0.95 . . no C8 H7 0.95 . . no C8 H8 0.95 . . no C8 H9 0.95 . . no C8' H10 0.95 . . no C8' H11 0.95 . . no C8' H12 0.95 . . no C9 H13 0.95 . . no C9 H14 0.95 . . no C9 H15 0.95 . . no C10 C11 1.527(3) . . yes C11 C15 1.546(3) . . yes C11 H16 0.95 . . no C14 H18 0.95 . . no C14 H19 0.95 . . no C14 H20 0.95 . . no C15 C16 1.503(3) . . yes C15 H21 0.95 . . no C15 H22 0.95 . . no C16 C17 1.395(4) . . yes C16 C21 1.380(4) . . yes C17 C18 1.381(4) . . yes C17 H23 0.95 . . no C18 C19 1.366(6) . . yes C18 H24 0.95 . . no C19 C20 1.372(5) . . yes C19 H25 0.95 . . no C20 C21 1.395(4) . . yes C20 H26 0.95 . . no C21 H27 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O22 C14 117.9(2) . . . yes N1 O25 C10 113.8(1) . . . yes O25 N1 C2 101.8(1) . . . yes O25 N1 C5 107.3(1) . . . yes C2 N1 C5 103.6(2) . . . yes C3 N4 C5 111.8(2) . . . yes C3 N4 C6 121.9(2) . . . yes C5 N4 C6 126.2(2) . . . yes C11 N12 C13 120.5(2) . . . yes C11 N12 H17 119.7 . . . no C13 N12 H17 119.8 . . . no N1 C2 C3 105.1(2) . . . yes N1 C2 H1 110.6 . . . no N1 C2 H2 110.6 . . . no C3 C2 H1 110.6 . . . no C3 C2 H2 110.6 . . . no H1 C2 H2 109.4 . . . no O26 C3 N4 126.1(3) . . . yes O26 C3 C2 126.4(2) . . . yes N4 C3 C2 107.6(2) . . . yes N1 C5 N4 103.4(1) . . . yes N1 C5 C7 104.7(2) . . . yes N1 C5 C9 112.5(2) . . . yes N4 C5 C7 111.4(2) . . . yes N4 C5 C9 111.2(2) . . . yes C7 C5 C9 113.1(2) . . . yes N4 C6 H3 109.5 . . . no N4 C6 H4 109.5 . . . no N4 C6 H5 109.5 . . . no H3 C6 H4 109.5 . . . no H3 C6 H5 109.5 . . . no H4 C6 H5 109.5 . . . no C5 C7 C8 111.9(2) . . . yes C5 C7 C8' 112.5(2) . . . yes C5 C7 H6 107.1 . . . no C8 C7 C8' 110.8(2) . . . yes C8 C7 H6 107.1 . . . no C8' C7 H6 107.1 . . . no C7 C8 H7 109.5 . . . no C7 C8 H8 109.5 . . . no C7 C8 H9 109.5 . . . no H7 C8 H8 109.5 . . . no H7 C8 H9 109.5 . . . no H8 C8 H9 109.5 . . . no C7 C8' H10 109.5 . . . no C7 C8' H11 109.5 . . . no C7 C8' H12 109.4 . . . no H10 C8' H11 109.4 . . . no H10 C8' H12 109.5 . . . no H11 C8' H12 109.5 . . . no C5 C9 H13 109.5 . . . no C5 C9 H14 109.5 . . . no C5 C9 H15 109.4 . . . no H13 C9 H14 109.5 . . . no H13 C9 H15 109.5 . . . no H14 C9 H15 109.5 . . . no O24 C10 O25 126.2(2) . . . yes O24 C10 C11 125.9(2) . . . yes O25 C10 C11 107.9(2) . . . yes N12 C11 C10 110.6(2) . . . yes N12 C11 C15 110.6(2) . . . yes N12 C11 H16 109.3 . . . no C10 C11 C15 107.6(2) . . . yes C10 C11 H16 109.3 . . . no C15 C11 H16 109.3 . . . no O22 C13 O23 123.7(2) . . . yes O22 C13 N12 111.3(2) . . . yes O23 C13 N12 124.9(2) . . . yes O22 C14 H18 109.5 . . . no O22 C14 H19 109.5 . . . no O22 C14 H20 109.5 . . . no H18 C14 H19 109.5 . . . no H18 C14 H20 109.5 . . . no H19 C14 H20 109.5 . . . no C11 C15 C16 114.3(2) . . . yes C11 C15 H21 108.2 . . . no C11 C15 H22 108.3 . . . no C16 C15 H21 108.2 . . . no C16 C15 H22 108.2 . . . no H21 C15 H22 109.5 . . . no C15 C16 C17 119.9(2) . . . yes C15 C16 C21 122.3(2) . . . yes C17 C16 C21 117.8(2) . . . yes C16 C17 C18 120.7(3) . . . yes C16 C17 H23 119.6 . . . no C18 C17 H23 119.6 . . . no C17 C18 C19 120.9(3) . . . yes C17 C18 H24 119.6 . . . no C19 C18 H24 119.5 . . . no C18 C19 C20 119.4(3) . . . yes C18 C19 H25 120.3 . . . no C20 C19 H25 120.3 . . . no C19 C20 C21 120.3(3) . . . yes C19 C20 H26 119.9 . . . no C21 C20 H26 119.9 . . . no C16 C21 C20 120.9(3) . . . yes C16 C21 H27 119.5 . . . no C20 C21 H27 119.6 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O22 O25 3.234(2) . 2_454 no O22 C11 3.518(3) . 2_454 no O22 O23 3.541(2) . 2_454 no O23 N12 2.959(2) . 2_444 no O23 C21 3.540(3) . 2_444 no O24 C6 3.360(4) . 1_565 no O24 C8' 3.491(4) . 2_554 no O25 C14 3.498(4) . 2_444 no O26 C2 3.200(3) . 2_443 no O26 C15 3.339(3) . 2_443 no #------------------------------------------------------------------------------ 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag ? ? ? ? ? ? ? ? ? ?