data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Runtao Li' _publ_contact_author_email LIRT@MAIL.BJMU.EDU.CN _publ_section_title ; Highly Enantioselective Michael Addition of Cyclopentanone with Chalcones Via Novel Di-iminium Mechanism ; loop_ _publ_author_name 'Runtao Li' 'Tieming Cheng' 'Zemei Ge' 'Junfeng Wang' 'Xin Wang' # Attachment 'w4460_0m.cif' data_w4460_0m _database_code_depnum_ccdc_archive 'CCDC 743201' #TrackingRef 'w4460_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H19 N O4' _chemical_formula_weight 337.36 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 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 P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.061(2) _cell_length_b 10.513(3) _cell_length_c 11.444(3) _cell_angle_alpha 67.430(4) _cell_angle_beta 80.858(4) _cell_angle_gamma 87.369(4) _cell_volume 884.1(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1869 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 22.27 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 356 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9665 _exptl_absorpt_correction_T_max 0.9838 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6605 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3262 _reflns_number_gt 2394 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0470P)^2^+0.1199P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00 _refine_ls_number_reflns 3262 _refine_ls_number_parameters 451 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 C1 C 0.2134(5) 0.7606(4) 0.1853(4) 0.0646(10) Uani 1 1 d . . . C2 C 0.1443(7) 0.6611(5) 0.1549(5) 0.0841(13) Uani 1 1 d . . . H2 H 0.0974 0.5809 0.2199 0.101 Uiso 1 1 calc R . . C3 C 0.1446(8) 0.6799(7) 0.0300(6) 0.112(2) Uani 1 1 d . . . H3 H 0.0963 0.6131 0.0107 0.134 Uiso 1 1 calc R . . C4 C 0.2152(10) 0.7957(9) -0.0668(6) 0.123(2) Uani 1 1 d . . . H4 H 0.2153 0.8076 -0.1516 0.148 Uiso 1 1 calc R . . C5 C 0.2859(8) 0.8945(7) -0.0384(6) 0.111(2) Uani 1 1 d . . . H5 H 0.3355 0.9729 -0.1043 0.134 Uiso 1 1 calc R . . C6 C 0.2837(7) 0.8785(5) 0.0857(5) 0.0885(15) Uani 1 1 d . . . H6 H 0.3296 0.9470 0.1040 0.106 Uiso 1 1 calc R . . C7 C 0.2166(5) 0.7460(4) 0.3191(4) 0.0613(10) Uani 1 1 d . . . C8 C 0.1676(5) 0.6087(4) 0.4255(4) 0.0571(9) Uani 1 1 d . . . H8A H 0.2547 0.5431 0.4215 0.069 Uiso 1 1 calc R . . H8B H 0.0648 0.5759 0.4117 0.069 Uiso 1 1 calc R . . C9 C 0.1407(4) 0.6129(4) 0.5592(3) 0.0505(8) Uani 1 1 d . . . H9 H 0.2311 0.6700 0.5626 0.061 Uiso 1 1 calc R . . C10 C -0.0239(4) 0.6797(4) 0.5834(4) 0.0519(9) Uani 1 1 d . . . C11 C -0.1756(5) 0.6285(4) 0.5745(5) 0.0757(13) Uani 1 1 d . . . H11 H -0.1756 0.5511 0.5539 0.091 Uiso 1 1 calc R . . C12 C -0.3251(5) 0.6897(5) 0.5955(5) 0.0795(13) Uani 1 1 d . . . H12 H -0.4256 0.6537 0.5900 0.095 Uiso 1 1 calc R . . C13 C -0.3247(5) 0.8041(4) 0.6244(4) 0.0560(9) Uani 1 1 d . . . C14 C -0.1788(4) 0.8580(4) 0.6334(4) 0.0594(10) Uani 1 1 d . . . H14 H -0.1803 0.9360 0.6532 0.071 Uiso 1 1 calc R . . C15 C -0.0289(4) 0.7954(4) 0.6127(4) 0.0573(9) Uani 1 1 d . . . H15 H 0.0708 0.8321 0.6187 0.069 Uiso 1 1 calc R . . C16 C 0.1525(5) 0.4690(4) 0.6623(3) 0.0557(9) Uani 1 1 d . . . H16 H 0.0794 0.4058 0.6484 0.067 Uiso 1 1 calc R . . C17 C 0.3314(5) 0.4125(4) 0.6612(4) 0.0649(10) Uani 1 1 d . . . C18 C 0.3666(7) 0.3438(7) 0.7939(5) 0.113(2) Uani 1 1 d . . . H18A H 0.4505 0.3956 0.8102 0.135 Uiso 1 1 calc R . . H18B H 0.4076 0.2515 0.8087 0.135 Uiso 1 1 calc R . . C19 C 0.2049(7) 0.3385(6) 0.8782(5) 0.110(2) Uani 1 1 d . . . H19A H 0.2237 0.3477 0.9562 0.132 Uiso 1 1 calc R . . H19B H 0.1457 0.2521 0.9006 0.132 Uiso 1 1 calc R . . C20 C 0.1054(7) 0.4582(5) 0.8014(4) 0.0836(13) Uani 1 1 d . . . H20A H 0.1357 0.5424 0.8093 0.100 Uiso 1 1 calc R . . H20B H -0.0142 0.4408 0.8301 0.100 Uiso 1 1 calc R . . C21 C 0.0642(4) 0.2125(3) 0.4880(4) 0.0490(8) Uani 1 1 d . . . C22 C -0.0926(5) 0.2748(4) 0.4871(4) 0.0605(10) Uani 1 1 d . . . H22 H -0.1250 0.3314 0.4095 0.073 Uiso 1 1 calc R . . C23 C -0.1996(5) 0.2536(4) 0.5990(5) 0.0657(11) Uani 1 1 d . . . H23 H -0.3042 0.2949 0.5968 0.079 Uiso 1 1 calc R . . C24 C -0.1526(5) 0.1717(5) 0.7145(5) 0.0687(11) Uani 1 1 d . . . H24 H -0.2251 0.1580 0.7902 0.082 Uiso 1 1 calc R . . C25 C 0.0018(5) 0.1099(4) 0.7182(4) 0.0645(10) Uani 1 1 d . . . H25 H 0.0335 0.0544 0.7964 0.077 Uiso 1 1 calc R . . C26 C 0.1095(5) 0.1304(4) 0.6058(4) 0.0562(9) Uani 1 1 d . . . H26 H 0.2138 0.0886 0.6089 0.067 Uiso 1 1 calc R . . C27 C 0.1720(4) 0.2355(4) 0.3632(4) 0.0540(9) Uani 1 1 d . . . C28 C 0.3315(5) 0.1557(4) 0.3608(4) 0.0546(9) Uani 1 1 d . . . H28A H 0.3025 0.0600 0.3824 0.066 Uiso 1 1 calc R . . H28B H 0.3922 0.1594 0.4262 0.066 Uiso 1 1 calc R . . C29 C 0.4480(5) 0.2085(4) 0.2316(3) 0.0515(9) Uani 1 1 d . . . H29 H 0.3811 0.2097 0.1668 0.062 Uiso 1 1 calc R . . C30 C 0.5131(4) 0.3545(4) 0.1923(3) 0.0498(8) Uani 1 1 d . . . C31 C 0.5408(5) 0.4083(4) 0.2811(4) 0.0611(10) Uani 1 1 d . . . H31 H 0.5190 0.3536 0.3680 0.073 Uiso 1 1 calc R . . C32 C 0.6005(5) 0.5422(5) 0.2423(5) 0.0734(12) Uani 1 1 d . . . H32 H 0.6155 0.5782 0.3026 0.088 Uiso 1 1 calc R . . C33 C 0.6367(6) 0.6196(4) 0.1157(5) 0.0745(12) Uani 1 1 d . . . C34 C 0.6147(7) 0.5704(5) 0.0245(5) 0.0869(15) Uani 1 1 d . . . H34 H 0.6422 0.6246 -0.0622 0.104 Uiso 1 1 calc R . . C35 C 0.5507(6) 0.4387(4) 0.0642(4) 0.0717(12) Uani 1 1 d . . . H35 H 0.5322 0.4053 0.0028 0.086 Uiso 1 1 calc R . . C36 C 0.5915(5) 0.1070(4) 0.2310(3) 0.0553(9) Uani 1 1 d . . . H36 H 0.5396 0.0148 0.2674 0.066 Uiso 1 1 calc R . . C37 C 0.6832(6) 0.1250(4) 0.1002(4) 0.0696(11) Uani 1 1 d . . . C38 C 0.8652(6) 0.0953(6) 0.1084(6) 0.0964(17) Uani 1 1 d . . . H38A H 0.9325 0.1794 0.0671 0.116 Uiso 1 1 calc R . . H38B H 0.9049 0.0315 0.0678 0.116 Uiso 1 1 calc R . . C39 C 0.8752(6) 0.0317(6) 0.2510(6) 0.0930(16) Uani 1 1 d . . . H39A H 0.9826 0.0523 0.2684 0.112 Uiso 1 1 calc R . . H39B H 0.8580 -0.0673 0.2849 0.112 Uiso 1 1 calc R . . C40 C 0.7315(5) 0.1018(5) 0.3070(4) 0.0757(12) Uani 1 1 d . . . H40A H 0.6968 0.0486 0.3974 0.091 Uiso 1 1 calc R . . H40B H 0.7646 0.1938 0.2958 0.091 Uiso 1 1 calc R . . N1 N -0.4832(4) 0.8732(4) 0.6427(3) 0.0683(9) Uani 1 1 d . . . N2 N 0.7010(6) 0.7628(5) 0.0754(7) 0.1100(16) Uani 1 1 d . . . O1 O 0.2593(5) 0.8415(3) 0.3422(3) 0.0934(10) Uani 1 1 d . . . O2 O -0.4799(4) 0.9814(4) 0.6562(4) 0.0901(10) Uani 1 1 d . . . O3 O -0.6121(4) 0.8192(4) 0.6414(4) 0.1057(12) Uani 1 1 d . . . O4 O 0.4320(4) 0.4292(4) 0.5666(3) 0.1022(12) Uani 1 1 d . . . O5 O 0.1294(4) 0.3148(3) 0.2637(3) 0.0794(9) Uani 1 1 d . . . O6 O 0.7101(8) 0.8041(5) 0.1593(7) 0.160(2) Uani 1 1 d . . . O7 O 0.7401(7) 0.8286(4) -0.0386(6) 0.156(2) Uani 1 1 d . . . O8 O 0.6179(6) 0.1588(4) 0.0057(3) 0.1144(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.063(2) 0.061(2) 0.064(3) -0.020(2) -0.007(2) 0.016(2) C2 0.103(4) 0.083(3) 0.070(3) -0.035(2) -0.011(3) 0.010(3) C3 0.145(6) 0.129(5) 0.076(4) -0.052(4) -0.029(4) 0.024(5) C4 0.150(6) 0.147(6) 0.062(4) -0.033(4) -0.020(4) 0.053(5) C5 0.121(5) 0.105(5) 0.068(4) 0.000(3) 0.005(3) 0.027(4) C6 0.090(4) 0.080(3) 0.074(3) -0.011(3) -0.001(3) 0.013(3) C7 0.058(2) 0.055(2) 0.070(3) -0.025(2) -0.0031(19) 0.0022(18) C8 0.063(2) 0.050(2) 0.061(2) -0.0253(18) -0.0110(18) 0.0059(17) C9 0.0469(19) 0.052(2) 0.059(2) -0.0282(18) -0.0080(16) 0.0003(16) C10 0.048(2) 0.052(2) 0.063(2) -0.0281(18) -0.0119(17) 0.0019(16) C11 0.059(3) 0.068(3) 0.121(4) -0.056(3) -0.020(2) -0.001(2) C12 0.043(2) 0.081(3) 0.129(4) -0.053(3) -0.016(2) -0.006(2) C13 0.045(2) 0.060(2) 0.065(2) -0.0276(19) -0.0081(17) 0.0069(17) C14 0.046(2) 0.058(2) 0.086(3) -0.038(2) -0.0151(19) 0.0039(18) C15 0.045(2) 0.059(2) 0.080(3) -0.039(2) -0.0140(18) 0.0035(17) C16 0.055(2) 0.058(2) 0.056(2) -0.0239(19) -0.0101(17) 0.0085(18) C17 0.065(3) 0.064(3) 0.065(3) -0.023(2) -0.013(2) 0.011(2) C18 0.088(4) 0.144(5) 0.073(3) -0.002(3) -0.024(3) 0.020(3) C19 0.088(4) 0.136(5) 0.066(3) 0.003(3) -0.006(3) 0.006(3) C20 0.091(3) 0.088(3) 0.065(3) -0.026(3) -0.005(2) 0.009(3) C21 0.0403(18) 0.0447(19) 0.067(2) -0.0276(18) -0.0068(16) 0.0029(15) C22 0.050(2) 0.053(2) 0.087(3) -0.034(2) -0.016(2) 0.0061(17) C23 0.048(2) 0.066(3) 0.093(3) -0.045(3) -0.004(2) 0.0081(19) C24 0.059(2) 0.073(3) 0.082(3) -0.044(3) 0.006(2) 0.000(2) C25 0.064(3) 0.067(3) 0.062(2) -0.028(2) 0.0010(19) 0.000(2) C26 0.048(2) 0.051(2) 0.071(3) -0.0261(19) -0.0101(18) 0.0114(16) C27 0.048(2) 0.047(2) 0.063(2) -0.0178(19) -0.0080(18) 0.0004(16) C28 0.053(2) 0.048(2) 0.057(2) -0.0179(17) -0.0002(17) 0.0043(16) C29 0.053(2) 0.054(2) 0.050(2) -0.0217(17) -0.0082(16) 0.0034(17) C30 0.051(2) 0.049(2) 0.050(2) -0.0209(16) -0.0064(15) 0.0074(15) C31 0.068(2) 0.058(2) 0.059(2) -0.0257(19) -0.0052(19) 0.0006(19) C32 0.067(3) 0.070(3) 0.099(4) -0.050(3) -0.013(2) 0.005(2) C33 0.069(3) 0.047(2) 0.099(4) -0.024(2) 0.002(2) -0.001(2) C34 0.106(4) 0.063(3) 0.067(3) -0.006(2) 0.005(3) 0.000(3) C35 0.103(3) 0.058(3) 0.049(2) -0.015(2) -0.009(2) -0.002(2) C36 0.058(2) 0.051(2) 0.053(2) -0.0199(17) 0.0036(17) 0.0028(17) C37 0.086(3) 0.058(2) 0.063(3) -0.028(2) 0.005(2) 0.006(2) C38 0.078(3) 0.092(4) 0.110(4) -0.046(3) 0.035(3) -0.014(3) C39 0.065(3) 0.101(4) 0.132(5) -0.066(4) -0.018(3) 0.019(3) C40 0.074(3) 0.082(3) 0.076(3) -0.036(2) -0.019(2) 0.022(2) N1 0.046(2) 0.089(3) 0.074(2) -0.036(2) -0.0117(17) 0.0075(19) N2 0.096(3) 0.065(3) 0.154(5) -0.031(4) 0.000(3) -0.010(2) O1 0.125(3) 0.066(2) 0.086(2) -0.0306(17) 0.0057(19) -0.0323(19) O2 0.0645(19) 0.088(2) 0.127(3) -0.054(2) -0.0137(18) 0.0223(17) O3 0.0455(17) 0.156(3) 0.148(3) -0.093(3) -0.0151(18) 0.0016(19) O4 0.086(2) 0.138(3) 0.080(2) -0.044(2) -0.0122(19) 0.049(2) O5 0.0674(18) 0.084(2) 0.069(2) -0.0106(16) -0.0136(15) 0.0165(16) O6 0.179(5) 0.094(3) 0.229(7) -0.083(4) -0.027(4) -0.029(3) O7 0.166(5) 0.072(3) 0.179(5) -0.010(3) 0.031(4) -0.033(3) O8 0.166(4) 0.117(3) 0.063(2) -0.044(2) -0.016(2) 0.052(3) _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 C2 1.387(6) . ? C1 C6 1.390(6) . ? C1 C7 1.483(6) . ? C2 C3 1.365(7) . ? C2 H2 0.9300 . ? C3 C4 1.364(9) . ? C3 H3 0.9300 . ? C4 C5 1.372(9) . ? C4 H4 0.9300 . ? C5 C6 1.362(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.209(5) . ? C7 C8 1.508(5) . ? C8 C9 1.528(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.509(5) . ? C9 C16 1.531(5) . ? C9 H9 0.9800 . ? C10 C15 1.379(5) . ? C10 C11 1.392(5) . ? C11 C12 1.371(6) . ? C11 H11 0.9300 . ? C12 C13 1.365(6) . ? C12 H12 0.9300 . ? C13 C14 1.364(5) . ? C13 N1 1.466(5) . ? C14 C15 1.380(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.534(5) . ? C16 C20 1.537(6) . ? C16 H16 0.9800 . ? C17 O4 1.203(5) . ? C17 C18 1.478(6) . ? C18 C19 1.483(8) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.510(7) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C26 1.389(5) . ? C21 C22 1.396(5) . ? C21 C27 1.487(5) . ? C22 C23 1.372(6) . ? C22 H22 0.9300 . ? C23 C24 1.373(6) . ? C23 H23 0.9300 . ? C24 C25 1.376(6) . ? C24 H24 0.9300 . ? C25 C26 1.380(5) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 O5 1.217(4) . ? C27 C28 1.505(5) . ? C28 C29 1.534(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.518(5) . ? C29 C36 1.538(5) . ? C29 H29 0.9800 . ? C30 C35 1.383(5) . ? C30 C31 1.388(5) . ? C31 C32 1.388(6) . ? C31 H31 0.9300 . ? C32 C33 1.352(7) . ? C32 H32 0.9300 . ? C33 C34 1.367(7) . ? C33 N2 1.488(6) . ? C34 C35 1.378(6) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C36 C37 1.506(5) . ? C36 C40 1.517(6) . ? C36 H36 0.9800 . ? C37 O8 1.201(5) . ? C37 C38 1.496(7) . ? C38 C39 1.522(8) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 C40 1.531(6) . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 H40A 0.9700 . ? C40 H40B 0.9700 . ? N1 O2 1.208(4) . ? N1 O3 1.212(4) . ? N2 O6 1.208(7) . ? N2 O7 1.215(7) . ? 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 C2 C1 C6 118.3(4) . . ? C2 C1 C7 122.9(4) . . ? C6 C1 C7 118.8(4) . . ? C3 C2 C1 120.4(5) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 120.7(6) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C3 C4 C5 119.7(6) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 120.3(6) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 120.6(6) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O1 C7 C1 120.8(4) . . ? O1 C7 C8 120.8(4) . . ? C1 C7 C8 118.4(4) . . ? C7 C8 C9 113.9(3) . . ? C7 C8 H8A 108.8 . . ? C9 C8 H8A 108.8 . . ? C7 C8 H8B 108.8 . . ? C9 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C10 C9 C8 110.8(3) . . ? C10 C9 C16 111.7(3) . . ? C8 C9 C16 111.3(3) . . ? C10 C9 H9 107.6 . . ? C8 C9 H9 107.6 . . ? C16 C9 H9 107.6 . . ? C15 C10 C11 117.6(3) . . ? C15 C10 C9 121.0(3) . . ? C11 C10 C9 121.4(3) . . ? C12 C11 C10 121.4(4) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C13 C12 C11 119.2(4) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C12 C13 C14 121.3(3) . . ? C12 C13 N1 119.7(3) . . ? C14 C13 N1 119.0(3) . . ? C13 C14 C15 119.2(3) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C10 C15 C14 121.3(3) . . ? C10 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C9 C16 C17 113.2(3) . . ? C9 C16 C20 115.6(3) . . ? C17 C16 C20 102.1(3) . . ? C9 C16 H16 108.5 . . ? C17 C16 H16 108.5 . . ? C20 C16 H16 108.5 . . ? O4 C17 C18 124.8(4) . . ? O4 C17 C16 125.2(4) . . ? C18 C17 C16 109.8(4) . . ? C17 C18 C19 106.0(4) . . ? C17 C18 H18A 110.5 . . ? C19 C18 H18A 110.5 . . ? C17 C18 H18B 110.5 . . ? C19 C18 H18B 110.5 . . ? H18A C18 H18B 108.7 . . ? C18 C19 C20 105.5(4) . . ? C18 C19 H19A 110.6 . . ? C20 C19 H19A 110.6 . . ? C18 C19 H19B 110.6 . . ? C20 C19 H19B 110.6 . . ? H19A C19 H19B 108.8 . . ? C19 C20 C16 104.9(4) . . ? C19 C20 H20A 110.8 . . ? C16 C20 H20A 110.8 . . ? C19 C20 H20B 110.8 . . ? C16 C20 H20B 110.8 . . ? H20A C20 H20B 108.8 . . ? C26 C21 C22 117.9(3) . . ? C26 C21 C27 123.6(3) . . ? C22 C21 C27 118.4(3) . . ? C23 C22 C21 121.0(4) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C22 C23 C24 120.2(4) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C25 120.1(4) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C24 C25 C26 120.0(4) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.9(3) . . ? C25 C26 H26 119.5 . . ? C21 C26 H26 119.5 . . ? O5 C27 C21 120.5(3) . . ? O5 C27 C28 120.1(3) . . ? C21 C27 C28 119.3(3) . . ? C27 C28 C29 114.1(3) . . ? C27 C28 H28A 108.7 . . ? C29 C28 H28A 108.7 . . ? C27 C28 H28B 108.7 . . ? C29 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? C30 C29 C28 113.6(3) . . ? C30 C29 C36 112.0(3) . . ? C28 C29 C36 110.3(3) . . ? C30 C29 H29 106.8 . . ? C28 C29 H29 106.8 . . ? C36 C29 H29 106.8 . . ? C35 C30 C31 117.3(4) . . ? C35 C30 C29 120.3(3) . . ? C31 C30 C29 122.4(3) . . ? C30 C31 C32 121.1(4) . . ? C30 C31 H31 119.5 . . ? C32 C31 H31 119.5 . . ? C33 C32 C31 119.1(4) . . ? C33 C32 H32 120.4 . . ? C31 C32 H32 120.4 . . ? C32 C33 C34 122.0(4) . . ? C32 C33 N2 118.6(5) . . ? C34 C33 N2 119.4(5) . . ? C33 C34 C35 118.3(4) . . ? C33 C34 H34 120.8 . . ? C35 C34 H34 120.8 . . ? C34 C35 C30 122.1(4) . . ? C34 C35 H35 119.0 . . ? C30 C35 H35 119.0 . . ? C37 C36 C40 103.7(3) . . ? C37 C36 C29 114.9(3) . . ? C40 C36 C29 118.2(3) . . ? C37 C36 H36 106.4 . . ? C40 C36 H36 106.4 . . ? C29 C36 H36 106.4 . . ? O8 C37 C38 126.6(4) . . ? O8 C37 C36 124.3(4) . . ? C38 C37 C36 109.0(4) . . ? C37 C38 C39 105.2(4) . . ? C37 C38 H38A 110.7 . . ? C39 C38 H38A 110.7 . . ? C37 C38 H38B 110.7 . . ? C39 C38 H38B 110.7 . . ? H38A C38 H38B 108.8 . . ? C38 C39 C40 102.5(4) . . ? C38 C39 H39A 111.3 . . ? C40 C39 H39A 111.3 . . ? C38 C39 H39B 111.3 . . ? C40 C39 H39B 111.3 . . ? H39A C39 H39B 109.2 . . ? C36 C40 C39 104.0(4) . . ? C36 C40 H40A 111.0 . . ? C39 C40 H40A 111.0 . . ? C36 C40 H40B 111.0 . . ? C39 C40 H40B 111.0 . . ? H40A C40 H40B 109.0 . . ? O2 N1 O3 123.0(4) . . ? O2 N1 C13 119.2(3) . . ? O3 N1 C13 117.8(4) . . ? O6 N2 O7 125.4(6) . . ? O6 N2 C33 117.0(6) . . ? O7 N2 C33 117.6(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.5(7) . . . . ? C7 C1 C2 C3 180.0(5) . . . . ? C1 C2 C3 C4 1.0(9) . . . . ? C2 C3 C4 C5 -0.3(10) . . . . ? C3 C4 C5 C6 -1.0(10) . . . . ? C4 C5 C6 C1 1.5(9) . . . . ? C2 C1 C6 C5 -0.7(7) . . . . ? C7 C1 C6 C5 178.8(5) . . . . ? C2 C1 C7 O1 -171.0(4) . . . . ? C6 C1 C7 O1 9.5(6) . . . . ? C2 C1 C7 C8 9.8(6) . . . . ? C6 C1 C7 C8 -169.7(4) . . . . ? O1 C7 C8 C9 12.6(5) . . . . ? C1 C7 C8 C9 -168.2(3) . . . . ? C7 C8 C9 C10 75.0(4) . . . . ? C7 C8 C9 C16 -160.1(3) . . . . ? C8 C9 C10 C15 -121.3(4) . . . . ? C16 C9 C10 C15 114.1(4) . . . . ? C8 C9 C10 C11 57.4(5) . . . . ? C16 C9 C10 C11 -67.2(5) . . . . ? C15 C10 C11 C12 -0.7(7) . . . . ? C9 C10 C11 C12 -179.5(5) . . . . ? C10 C11 C12 C13 0.6(8) . . . . ? C11 C12 C13 C14 -0.3(7) . . . . ? C11 C12 C13 N1 177.9(4) . . . . ? C12 C13 C14 C15 0.0(6) . . . . ? N1 C13 C14 C15 -178.2(4) . . . . ? C11 C10 C15 C14 0.4(6) . . . . ? C9 C10 C15 C14 179.2(4) . . . . ? C13 C14 C15 C10 -0.1(6) . . . . ? C10 C9 C16 C17 -165.5(3) . . . . ? C8 C9 C16 C17 70.2(4) . . . . ? C10 C9 C16 C20 -48.3(4) . . . . ? C8 C9 C16 C20 -172.6(3) . . . . ? C9 C16 C17 O4 -37.6(6) . . . . ? C20 C16 C17 O4 -162.6(5) . . . . ? C9 C16 C17 C18 138.1(4) . . . . ? C20 C16 C17 C18 13.1(5) . . . . ? O4 C17 C18 C19 -176.3(5) . . . . ? C16 C17 C18 C19 8.0(7) . . . . ? C17 C18 C19 C20 -26.5(7) . . . . ? C18 C19 C20 C16 35.1(6) . . . . ? C9 C16 C20 C19 -152.2(4) . . . . ? C17 C16 C20 C19 -28.9(5) . . . . ? C26 C21 C22 C23 -1.0(5) . . . . ? C27 C21 C22 C23 177.9(3) . . . . ? C21 C22 C23 C24 0.8(6) . . . . ? C22 C23 C24 C25 -0.4(6) . . . . ? C23 C24 C25 C26 0.1(6) . . . . ? C24 C25 C26 C21 -0.2(6) . . . . ? C22 C21 C26 C25 0.7(5) . . . . ? C27 C21 C26 C25 -178.1(3) . . . . ? C26 C21 C27 O5 -175.8(4) . . . . ? C22 C21 C27 O5 5.3(5) . . . . ? C26 C21 C27 C28 6.4(5) . . . . ? C22 C21 C27 C28 -172.4(3) . . . . ? O5 C27 C28 C29 13.7(5) . . . . ? C21 C27 C28 C29 -168.5(3) . . . . ? C27 C28 C29 C30 62.9(4) . . . . ? C27 C28 C29 C36 -170.3(3) . . . . ? C28 C29 C30 C35 -150.2(4) . . . . ? C36 C29 C30 C35 83.9(4) . . . . ? C28 C29 C30 C31 31.2(5) . . . . ? C36 C29 C30 C31 -94.6(4) . . . . ? C35 C30 C31 C32 1.3(6) . . . . ? C29 C30 C31 C32 180.0(3) . . . . ? C30 C31 C32 C33 -1.9(6) . . . . ? C31 C32 C33 C34 0.6(7) . . . . ? C31 C32 C33 N2 -179.8(4) . . . . ? C32 C33 C34 C35 1.2(7) . . . . ? N2 C33 C34 C35 -178.3(4) . . . . ? C33 C34 C35 C30 -1.9(7) . . . . ? C31 C30 C35 C34 0.6(6) . . . . ? C29 C30 C35 C34 -178.1(4) . . . . ? C30 C29 C36 C37 -69.4(4) . . . . ? C28 C29 C36 C37 163.0(3) . . . . ? C30 C29 C36 C40 53.6(4) . . . . ? C28 C29 C36 C40 -74.0(4) . . . . ? C40 C36 C37 O8 -165.7(4) . . . . ? C29 C36 C37 O8 -35.2(6) . . . . ? C40 C36 C37 C38 13.9(5) . . . . ? C29 C36 C37 C38 144.3(4) . . . . ? O8 C37 C38 C39 -169.6(5) . . . . ? C36 C37 C38 C39 10.9(5) . . . . ? C37 C38 C39 C40 -30.9(5) . . . . ? C37 C36 C40 C39 -33.1(5) . . . . ? C29 C36 C40 C39 -161.6(4) . . . . ? C38 C39 C40 C36 39.9(5) . . . . ? C12 C13 N1 O2 -173.0(4) . . . . ? C14 C13 N1 O2 5.2(6) . . . . ? C12 C13 N1 O3 5.8(6) . . . . ? C14 C13 N1 O3 -176.0(4) . . . . ? C32 C33 N2 O6 -3.3(8) . . . . ? C34 C33 N2 O6 176.3(6) . . . . ? C32 C33 N2 O7 176.7(5) . . . . ? C34 C33 N2 O7 -3.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.120 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.028 _chemical_absolute_configuration syn