# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author # name and address of author for correspondence ; Dr X. Moreau Institut Lavoisier de Versailles, ILV, UMR CNRS 8180 Universit\'e de Versailles Saint-Quentin-en-Yvelines 45 Avenue des Etats Unis 78035 Versailles Cedex France ; _publ_contact_author_phone '(33) 1 39 25 44 05 ' _publ_contact_author_fax '(33) 1 39 25 44 52' _publ_contact_author_email moreau@chimie.uvsq.fr _publ_requested_coeditor_name ? _publ_contact_letter ; ; #==================================================================== # 2. processing summary (iucr office use only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ; _journal_techeditor_code ? _journal_techeditor_notes ; ; _journal_coden_astm ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #==================================================================== # 3. title and author list _publ_section_title ; Asymmetric Organocatalytic Michael/\a-Amination Sequence for the Construction of a Quaternary Stereogenic Center ; # the loop structure below should contain the names and addresses of all # authors, in the required order of publication. repeat as necessary. loop_ _publ_author_name _publ_author_address A.Desmarchelier ; Institut Lavoisier de Versailles, ILV, UMR CNRS 8180 Universit\'e de Versailles Saint-Quentin-en-Yvelines 45 Avenue des Etats Unis 78035 Versailles Cedex France ; J.Marrot ; Institut Lavoisier de Versailles, ILV, UMR CNRS 8180 Universit\'e de Versailles Saint-Quentin-en-Yvelines 45 Avenue des Etats Unis 78035 Versailles Cedex France ; X.Moreau ; Institut Lavoisier de Versailles, ILV, UMR CNRS 8180 Universit\'e de Versailles Saint-Quentin-en-Yvelines 45 Avenue des Etats Unis 78035 Versailles Cedex France ; C.Greck ; Institut Lavoisier de Versailles, ILV, UMR CNRS 8180 Universit\'e de Versailles Saint-Quentin-en-Yvelines 45 Avenue des Etats Unis 78035 Versailles Cedex France ; #==================================================================== # 4. text _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_experimental ; ; _publ_section_references ; sheldrick, g.m. (1993). shelxl-93. program for crystal structure determination. univ. of g\"ottingen, federal republic of germany. sheldrick, g.m. (1997). shelxs-86. program for the solution of crystal structures. univ. of g\"ottingen, federal republic of germany. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; #==================================================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 784199' #TrackingRef 'data3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H31 N3 O7' _chemical_formula_weight 437.49 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.158(3) _cell_length_b 14.069(4) _cell_length_c 17.637(4) _cell_angle_alpha 90.00 _cell_angle_beta 99.962(11) _cell_angle_gamma 90.00 _cell_volume 2482.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 8032 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 24.84 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _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 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9698 _exptl_absorpt_correction_T_max 0.9826 _exptl_absorpt_process_details 'SADABS (Sheldrick, V2.10)' _exptl_special_details ; 'Blessing, Acta Cryst. (1995) A51, 33-38' ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 512x512 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 136829 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4347 _reflns_number_gt 4107 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1137P)^2^+0.7703P] 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 4347 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0861 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.2158 _refine_ls_wR_factor_gt 0.1933 _refine_ls_goodness_of_fit_ref 1.216 _refine_ls_restrained_S_all 1.216 _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 0.19153(18) 0.98375(13) 0.91710(11) 0.0743(5) Uani 1 1 d . . . O2 O 0.16713(19) 0.64792(13) 0.93447(12) 0.0739(5) Uani 1 1 d . . . O3 O 0.31797(19) 0.53198(12) 0.92052(13) 0.0744(5) Uani 1 1 d . . . O4 O 0.14542(16) 0.83731(11) 0.76766(9) 0.0607(4) Uani 1 1 d . . . O5 O 0.19078(16) 0.67953(12) 0.75785(9) 0.0613(5) Uani 1 1 d . . . O6 O 0.4922(3) 1.0448(2) 0.71269(16) 0.1195(10) Uani 1 1 d . . . O7 O 0.4962(3) 1.10323(17) 0.82345(16) 0.1103(9) Uani 1 1 d . . . N1 N 0.30356(16) 0.76347(11) 0.85427(9) 0.0425(4) Uani 1 1 d . . . N2 N 0.35419(17) 0.67678(12) 0.88311(10) 0.0466(4) Uani 1 1 d . . . H12 H 0.4349 0.6596 0.8814 0.056 Uiso 1 1 calc R . . N3 N 0.4617(2) 1.04362(17) 0.77545(14) 0.0718(6) Uani 1 1 d . . . C1 C 0.6743(2) 0.89025(16) 0.92799(14) 0.0557(5) Uani 1 1 d . . . H1 H 0.6636 0.9329 0.9667 0.067 Uiso 1 1 calc R . . C2 C 0.7966(3) 0.8468(2) 0.92967(19) 0.0728(7) Uani 1 1 d . . . H2 H 0.8671 0.8602 0.9694 0.087 Uiso 1 1 calc R . . C3 C 0.8144(3) 0.7840(2) 0.8728(2) 0.0840(9) Uani 1 1 d . . . H3 H 0.8965 0.7543 0.8740 0.101 Uiso 1 1 calc R . . C4 C 0.7097(3) 0.7651(2) 0.8140(2) 0.0871(9) Uani 1 1 d . . . H4 H 0.7217 0.7229 0.7752 0.105 Uiso 1 1 calc R . . C5 C 0.5871(3) 0.8083(2) 0.81198(15) 0.0653(7) Uani 1 1 d . . . H5 H 0.5175 0.7950 0.7718 0.078 Uiso 1 1 calc R . . C6 C 0.5667(2) 0.87160(14) 0.86958(12) 0.0464(5) Uani 1 1 d . . . C7 C 0.4325(2) 0.91841(14) 0.87031(11) 0.0446(5) Uani 1 1 d . . . H7 H 0.4495 0.9708 0.9073 0.053 Uiso 1 1 calc R . . C8 C 0.33316(19) 0.85006(13) 0.90150(11) 0.0422(5) Uani 1 1 d . . . C9 C 0.3916(2) 0.82283(16) 0.98498(11) 0.0526(5) Uani 1 1 d . . . H9A H 0.4741 0.7891 0.9860 0.079 Uiso 1 1 calc R . . H9B H 0.3293 0.7831 1.0054 0.079 Uiso 1 1 calc R . . H9C H 0.4080 0.8794 1.0156 0.079 Uiso 1 1 calc R . . C10 C 0.2019(2) 0.89963(17) 0.90861(13) 0.0560(6) Uani 1 1 d . . . H10 H 0.1257 0.8624 0.9062 0.067 Uiso 1 1 calc R . . C11 C 0.3731(2) 0.96347(17) 0.79322(14) 0.0587(6) Uani 1 1 d . . . H11A H 0.3654 0.9160 0.7528 0.070 Uiso 1 1 calc R . . H11B H 0.2844 0.9876 0.7954 0.070 Uiso 1 1 calc R . . C12 C 0.2673(2) 0.61938(15) 0.91486(14) 0.0551(5) Uani 1 1 d . . . C13 C 0.2552(4) 0.4554(2) 0.9595(3) 0.1036(13) Uani 1 1 d . . . C14 C 0.1150(5) 0.4391(3) 0.9176(4) 0.141(2) Uani 1 1 d . . . H14A H 0.1159 0.4320 0.8635 0.211 Uiso 1 1 calc R . . H14B H 0.0601 0.4924 0.9256 0.211 Uiso 1 1 calc R . . H14C H 0.0797 0.3824 0.9368 0.211 Uiso 1 1 calc R . . C15 C 0.3440(5) 0.3718(3) 0.9491(4) 0.160(3) Uani 1 1 d . . . H15A H 0.4317 0.3823 0.9784 0.239 Uiso 1 1 calc R . . H15B H 0.3499 0.3653 0.8956 0.239 Uiso 1 1 calc R . . H15C H 0.3069 0.3149 0.9668 0.239 Uiso 1 1 calc R . . C16 C 0.2634(7) 0.4826(4) 1.0434(3) 0.161(2) Uani 1 1 d . . . H16A H 0.2140 0.5402 1.0469 0.242 Uiso 1 1 calc R . . H16B H 0.3552 0.4924 1.0664 0.242 Uiso 1 1 calc R . . H16C H 0.2263 0.4326 1.0701 0.242 Uiso 1 1 calc R . . C17 C 0.2049(2) 0.76493(15) 0.78969(12) 0.0471(5) Uani 1 1 d . . . C18 C 0.0973(2) 0.6618(2) 0.68498(16) 0.0749(8) Uani 1 1 d . . . C19 C 0.1372(4) 0.7258(4) 0.62271(19) 0.1223(17) Uani 1 1 d . . . H19A H 0.0834 0.7107 0.5739 0.183 Uiso 1 1 calc R . . H19B H 0.2297 0.7158 0.6200 0.183 Uiso 1 1 calc R . . H19C H 0.1235 0.7911 0.6351 0.183 Uiso 1 1 calc R . . C20 C 0.1204(4) 0.5571(3) 0.6723(3) 0.132(2) Uani 1 1 d . . . H20A H 0.1027 0.5216 0.7160 0.198 Uiso 1 1 calc R . . H20B H 0.2114 0.5473 0.6661 0.198 Uiso 1 1 calc R . . H20C H 0.0615 0.5361 0.6269 0.198 Uiso 1 1 calc R . . C21 C -0.0440(3) 0.6794(2) 0.6960(2) 0.0863(10) Uani 1 1 d . . . H21A H -0.0631 0.6416 0.7381 0.129 Uiso 1 1 calc R . . H21B H -0.1043 0.6625 0.6499 0.129 Uiso 1 1 calc R . . H21C H -0.0550 0.7455 0.7071 0.129 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 0.0693(11) 0.0630(11) 0.0872(13) -0.0217(9) 0.0044(9) 0.0183(8) O2 0.0688(11) 0.0659(11) 0.0948(13) 0.0071(9) 0.0363(10) -0.0039(9) O3 0.0726(11) 0.0429(9) 0.1066(14) 0.0156(9) 0.0125(10) -0.0016(8) O4 0.0577(9) 0.0548(9) 0.0642(10) 0.0015(7) -0.0047(7) 0.0022(7) O5 0.0578(9) 0.0608(10) 0.0608(9) -0.0208(8) -0.0018(7) 0.0001(7) O6 0.143(2) 0.131(2) 0.0914(16) 0.0289(15) 0.0379(15) -0.0507(18) O7 0.144(2) 0.0726(14) 0.1068(18) 0.0111(13) -0.0001(16) -0.0461(15) N1 0.0462(9) 0.0365(8) 0.0443(8) -0.0014(6) 0.0064(7) -0.0013(6) N2 0.0451(9) 0.0391(9) 0.0564(10) 0.0015(7) 0.0109(7) 0.0018(7) N3 0.0694(13) 0.0658(14) 0.0749(14) 0.0269(12) -0.0024(11) -0.0126(10) C1 0.0525(12) 0.0507(12) 0.0620(13) 0.0025(10) 0.0047(10) -0.0045(9) C2 0.0479(13) 0.0738(17) 0.0923(19) 0.0125(15) -0.0004(12) -0.0059(12) C3 0.0501(14) 0.0760(18) 0.132(3) 0.0042(18) 0.0325(16) 0.0031(13) C4 0.0668(17) 0.086(2) 0.119(2) -0.0310(18) 0.0451(17) -0.0093(14) C5 0.0544(13) 0.0768(16) 0.0686(15) -0.0158(12) 0.0213(11) -0.0113(11) C6 0.0480(11) 0.0429(10) 0.0494(11) 0.0033(8) 0.0115(8) -0.0064(8) C7 0.0484(11) 0.0383(10) 0.0456(10) 0.0009(8) 0.0040(8) -0.0031(8) C8 0.0460(10) 0.0390(10) 0.0419(10) -0.0025(8) 0.0086(8) -0.0005(8) C9 0.0661(13) 0.0528(12) 0.0397(10) -0.0021(9) 0.0109(9) -0.0028(10) C10 0.0512(12) 0.0591(14) 0.0580(12) -0.0107(10) 0.0104(9) 0.0030(10) C11 0.0550(12) 0.0567(13) 0.0608(13) 0.0154(10) 0.0000(10) -0.0108(10) C12 0.0587(13) 0.0421(11) 0.0638(13) 0.0025(9) 0.0090(10) -0.0062(9) C13 0.090(2) 0.0558(17) 0.157(4) 0.038(2) 0.000(2) -0.0196(15) C14 0.102(3) 0.081(2) 0.225(6) 0.021(3) -0.010(3) -0.036(2) C15 0.133(4) 0.055(2) 0.283(8) 0.056(3) 0.014(4) 0.004(2) C16 0.196(6) 0.154(4) 0.126(4) 0.076(4) 0.007(4) -0.052(4) C17 0.0456(10) 0.0476(11) 0.0486(11) -0.0051(9) 0.0098(8) -0.0052(9) C18 0.0448(12) 0.105(2) 0.0709(16) -0.0465(15) 0.0002(11) 0.0050(12) C19 0.088(2) 0.227(5) 0.0537(16) -0.018(2) 0.0190(15) 0.008(3) C20 0.081(2) 0.129(3) 0.168(4) -0.107(3) -0.028(2) 0.024(2) C21 0.0465(13) 0.100(2) 0.113(2) -0.0426(19) 0.0134(14) -0.0050(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 C10 1.200(3) . ? O2 C12 1.199(3) . ? O3 C12 1.330(3) . ? O3 C13 1.480(4) . ? O4 C17 1.213(3) . ? O5 C17 1.324(3) . ? O5 C18 1.481(3) . ? O6 N3 1.200(4) . ? O7 N3 1.200(3) . ? N1 C17 1.381(3) . ? N1 N2 1.386(2) . ? N1 C8 1.477(2) . ? N2 C12 1.384(3) . ? N2 H12 0.8600 . ? N3 C11 1.509(3) . ? C1 C2 1.380(4) . ? C1 C6 1.391(3) . ? C1 H1 0.9300 . ? C2 C3 1.372(5) . ? C2 H2 0.9300 . ? C3 C4 1.377(5) . ? C3 H3 0.9300 . ? C4 C5 1.380(4) . ? C4 H4 0.9300 . ? C5 C6 1.393(3) . ? C5 H5 0.9300 . ? C6 C7 1.516(3) . ? C7 C11 1.527(3) . ? C7 C8 1.561(3) . ? C7 H7 0.9800 . ? C8 C10 1.528(3) . ? C8 C9 1.538(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 C14 1.504(6) . ? C13 C15 1.513(6) . ? C13 C16 1.518(8) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C18 C21 1.502(4) . ? C18 C20 1.514(5) . ? C18 C19 1.528(6) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 C12 O3 C13 121.0(2) . . ? C17 O5 C18 121.82(19) . . ? C17 N1 N2 119.08(16) . . ? C17 N1 C8 120.05(16) . . ? N2 N1 C8 119.51(15) . . ? C12 N2 N1 116.09(17) . . ? C12 N2 H12 122.0 . . ? N1 N2 H12 122.0 . . ? O6 N3 O7 123.4(3) . . ? O6 N3 C11 117.4(3) . . ? O7 N3 C11 119.2(2) . . ? C2 C1 C6 121.4(2) . . ? C2 C1 H1 119.3 . . ? C6 C1 H1 119.3 . . ? C3 C2 C1 120.1(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.5(3) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 120.7(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 117.6(2) . . ? C1 C6 C7 120.28(19) . . ? C5 C6 C7 122.09(19) . . ? C6 C7 C11 112.96(18) . . ? C6 C7 C8 111.87(16) . . ? C11 C7 C8 112.93(17) . . ? C6 C7 H7 106.1 . . ? C11 C7 H7 106.1 . . ? C8 C7 H7 106.1 . . ? N1 C8 C10 109.10(16) . . ? N1 C8 C9 109.98(16) . . ? C10 C8 C9 103.48(16) . . ? N1 C8 C7 112.96(15) . . ? C10 C8 C7 111.96(17) . . ? C9 C8 C7 108.93(16) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 C10 C8 123.9(2) . . ? O1 C10 H10 118.1 . . ? C8 C10 H10 118.1 . . ? N3 C11 C7 109.72(18) . . ? N3 C11 H11A 109.7 . . ? C7 C11 H11A 109.7 . . ? N3 C11 H11B 109.7 . . ? C7 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? O2 C12 O3 128.7(2) . . ? O2 C12 N2 123.6(2) . . ? O3 C12 N2 107.7(2) . . ? O3 C13 C14 109.3(3) . . ? O3 C13 C15 101.3(4) . . ? C14 C13 C15 110.9(4) . . ? O3 C13 C16 108.3(3) . . ? C14 C13 C16 113.9(5) . . ? C15 C13 C16 112.4(4) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O4 C17 O5 127.93(19) . . ? O4 C17 N1 121.79(18) . . ? O5 C17 N1 110.27(17) . . ? O5 C18 C21 110.1(2) . . ? O5 C18 C20 101.5(2) . . ? C21 C18 C20 110.8(3) . . ? O5 C18 C19 108.3(2) . . ? C21 C18 C19 111.9(3) . . ? C20 C18 C19 113.6(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C18 C21 H21A 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C18 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.532 _refine_diff_density_min -0.624 _refine_diff_density_rms 0.208 #===END