# Supplementary Material (ESI) for Catalysis Science & Technology # This journal is (c) The Royal Society of Chemistry 2011 data_global loop_ _publ_author_name 'Fossey, John' 'Deng, Wei-Ping' _publ_contact_author_name 'Deng, Wei-Ping' _publ_contact_author_email weiping_deng@ecust.edu.cn _publ_section_title ; Novel N,O-Cu(OAc)2 complex catalysed diastereo- and enantioselective 1,4-addition of glycine derivatives to alkylidene malonates. ; # Attachment '- cd201415.cif' data_cd201415 _database_code_depnum_ccdc_archive 'CCDC 795643' #TrackingRef '- cd201415.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H27 N O6' _chemical_formula_weight 473.51 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.4200(17) _cell_length_b 12.888(2) _cell_length_c 19.103(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2565.4(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 922 _cell_measurement_theta_min 5.461 _cell_measurement_theta_max 37.314 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.402 _exptl_crystal_size_mid 0.349 _exptl_crystal_size_min 0.311 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3842 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 11182 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 23.27 _reflns_number_total 2125 _reflns_number_gt 1731 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0489P)^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 SHELXL _refine_ls_extinction_coef 0.0043(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _chemical_absolute_configuration unk _refine_ls_number_reflns 2125 _refine_ls_number_parameters 320 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_ref 0.0852 _refine_ls_wR_factor_gt 0.0814 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _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 0.1640(3) 0.1591(2) 0.37324(14) 0.0941(8) Uani 1 1 d . . . O2 O 0.1393(3) 0.32968(19) 0.36328(13) 0.0892(8) Uani 1 1 d . . . O3 O 0.4591(3) 0.20807(19) 0.40693(13) 0.0883(8) Uani 1 1 d . . . O4 O 0.4958(3) 0.35763(17) 0.35446(13) 0.0860(8) Uani 1 1 d . . . O5 O 0.0285(2) 0.1601(2) 0.22644(15) 0.1000(9) Uani 1 1 d . . . O6 O 0.1467(2) 0.01609(17) 0.24062(13) 0.0828(7) Uani 1 1 d . . . N1 N 0.2360(2) 0.26495(18) 0.17004(12) 0.0546(7) Uani 1 1 d . . . C1 C 0.2538(3) 0.1621(2) 0.20031(14) 0.0515(7) Uani 1 1 d . . . H1 H 0.2895 0.1168 0.1640 0.062 Uiso 1 1 calc R . . C2 C 0.3538(3) 0.1698(2) 0.26079(13) 0.0470(7) Uani 1 1 d . . . H2 H 0.3497 0.1049 0.2874 0.056 Uiso 1 1 calc R . . C3 C 0.3232(3) 0.2597(2) 0.31201(14) 0.0516(7) Uani 1 1 d . . . H3 H 0.3151 0.3245 0.2855 0.062 Uiso 1 1 calc R . . C4 C 0.1996(3) 0.2407(3) 0.35268(15) 0.0618(8) Uani 1 1 d . . . C5 C 0.0180(5) 0.3207(4) 0.4008(3) 0.138(2) Uani 1 1 d . . . H5A H -0.0382 0.2747 0.3758 0.207 Uiso 1 1 calc R . . H5B H -0.0212 0.3878 0.4045 0.207 Uiso 1 1 calc R . . H5C H 0.0335 0.2935 0.4468 0.207 Uiso 1 1 calc R . . C6 C 0.4321(3) 0.2702(2) 0.36398(17) 0.0586(8) Uani 1 1 d . . . C7 C 0.6098(5) 0.3716(3) 0.3976(3) 0.1302(19) Uani 1 1 d . . . H7A H 0.5871 0.3651 0.4461 0.195 Uiso 1 1 calc R . . H7B H 0.6453 0.4393 0.3893 0.195 Uiso 1 1 calc R . . H7C H 0.6722 0.3197 0.3857 0.195 Uiso 1 1 calc R . . C8 C 0.1292(4) 0.1164(3) 0.22391(16) 0.0645(9) Uani 1 1 d . . . C9 C 0.0368(4) -0.0369(3) 0.2719(2) 0.1182(16) Uani 1 1 d . . . H9A H 0.0173 -0.0058 0.3163 0.177 Uiso 1 1 calc R . . H9B H 0.0571 -0.1089 0.2785 0.177 Uiso 1 1 calc R . . H9C H -0.0360 -0.0307 0.2414 0.177 Uiso 1 1 calc R . . C10 C 0.4882(3) 0.1793(2) 0.23132(13) 0.0498(7) Uani 1 1 d . . . C11 C 0.5705(3) 0.0962(3) 0.23402(18) 0.0736(10) Uani 1 1 d . . . H11 H 0.5433 0.0342 0.2540 0.088 Uiso 1 1 calc R . . C12 C 0.6933(4) 0.1038(4) 0.2074(2) 0.0988(14) Uani 1 1 d . . . H12 H 0.7483 0.0471 0.2103 0.119 Uiso 1 1 calc R . . C13 C 0.7345(4) 0.1922(4) 0.17731(19) 0.0964(14) Uani 1 1 d . . . H13 H 0.8173 0.1965 0.1594 0.116 Uiso 1 1 calc R . . C14 C 0.6543(4) 0.2753(3) 0.17336(19) 0.0909(12) Uani 1 1 d . . . H14 H 0.6827 0.3366 0.1529 0.109 Uiso 1 1 calc R . . C15 C 0.5320(3) 0.2692(3) 0.19932(18) 0.0738(10) Uani 1 1 d . . . H15 H 0.4775 0.3260 0.1954 0.089 Uiso 1 1 calc R . . C16 C 0.2200(3) 0.2747(2) 0.10439(14) 0.0461(7) Uani 1 1 d . . . C17 C 0.2084(3) 0.1865(2) 0.05435(14) 0.0522(7) Uani 1 1 d . . . C18 C 0.0897(4) 0.1420(3) 0.04238(18) 0.0758(10) Uani 1 1 d . . . H18 H 0.0174 0.1679 0.0649 0.091 Uiso 1 1 calc R . . C19 C 0.0784(5) 0.0592(3) -0.0029(2) 0.0986(14) Uani 1 1 d . . . H19 H -0.0016 0.0294 -0.0109 0.118 Uiso 1 1 calc R . . C20 C 0.1833(7) 0.0212(3) -0.0357(2) 0.1071(18) Uani 1 1 d . . . H20 H 0.1746 -0.0347 -0.0661 0.129 Uiso 1 1 calc R . . C21 C 0.3013(5) 0.0632(3) -0.02492(19) 0.0936(14) Uani 1 1 d . . . H21 H 0.3727 0.0359 -0.0476 0.112 Uiso 1 1 calc R . . C22 C 0.3145(4) 0.1473(3) 0.02017(15) 0.0691(9) Uani 1 1 d . . . H22 H 0.3948 0.1771 0.0273 0.083 Uiso 1 1 calc R . . C23 C 0.2129(3) 0.3822(2) 0.07508(14) 0.0509(7) Uani 1 1 d . . . C24 C 0.1877(4) 0.4003(2) 0.00602(16) 0.0702(10) Uani 1 1 d . . . H24 H 0.1723 0.3444 -0.0237 0.084 Uiso 1 1 calc R . . C25 C 0.1846(4) 0.4998(3) -0.02065(18) 0.0885(12) Uani 1 1 d . . . H25 H 0.1676 0.5107 -0.0679 0.106 Uiso 1 1 calc R . . C26 C 0.2066(5) 0.5821(3) 0.0224(2) 0.0916(13) Uani 1 1 d . . . H26 H 0.2027 0.6494 0.0050 0.110 Uiso 1 1 calc R . . C27 C 0.2345(4) 0.5653(3) 0.0916(2) 0.0900(12) Uani 1 1 d . . . H27 H 0.2515 0.6211 0.1210 0.108 Uiso 1 1 calc R . . C28 C 0.2373(4) 0.4664(2) 0.11745(16) 0.0690(9) Uani 1 1 d . . . H28 H 0.2561 0.4558 0.1645 0.083 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 0.090(2) 0.0833(17) 0.109(2) 0.0227(16) 0.0316(16) -0.0021(15) O2 0.0834(18) 0.0827(16) 0.1013(18) -0.0174(15) 0.0215(16) 0.0214(15) O3 0.106(2) 0.0832(16) 0.0762(16) 0.0222(14) -0.0359(15) -0.0161(14) O4 0.0968(19) 0.0614(15) 0.0999(18) -0.0015(13) -0.0180(15) -0.0208(14) O5 0.0511(16) 0.118(2) 0.131(2) 0.0313(18) -0.0071(15) 0.0092(15) O6 0.0740(16) 0.0637(14) 0.1108(18) 0.0117(13) -0.0039(14) -0.0157(13) N1 0.0649(17) 0.0507(14) 0.0483(15) 0.0000(11) -0.0067(12) 0.0090(13) C1 0.058(2) 0.0466(17) 0.0497(16) -0.0011(13) -0.0045(14) 0.0049(15) C2 0.0535(17) 0.0412(14) 0.0462(15) 0.0035(13) -0.0044(14) 0.0042(14) C3 0.0582(19) 0.0469(16) 0.0498(16) 0.0036(14) -0.0004(14) 0.0020(14) C4 0.064(2) 0.070(2) 0.0512(18) -0.0025(17) 0.0007(16) 0.012(2) C5 0.103(4) 0.149(4) 0.163(4) -0.036(4) 0.059(4) 0.027(3) C6 0.072(2) 0.0515(18) 0.0522(19) -0.0037(16) 0.0016(17) -0.0018(17) C7 0.113(4) 0.110(3) 0.168(5) -0.021(3) -0.043(4) -0.042(3) C8 0.058(2) 0.071(2) 0.064(2) 0.0042(17) -0.0127(18) 0.0023(19) C9 0.094(3) 0.112(3) 0.149(4) 0.035(3) -0.006(3) -0.046(3) C10 0.0530(19) 0.0547(18) 0.0416(17) -0.0002(14) -0.0037(14) 0.0045(15) C11 0.067(2) 0.078(2) 0.076(2) 0.0101(19) 0.003(2) 0.0207(19) C12 0.075(3) 0.128(4) 0.094(3) 0.018(3) 0.014(2) 0.042(3) C13 0.054(2) 0.168(4) 0.068(2) 0.017(3) 0.0103(19) 0.013(3) C14 0.068(3) 0.115(3) 0.089(3) 0.031(2) 0.011(2) -0.008(3) C15 0.063(2) 0.073(2) 0.086(2) 0.014(2) 0.0106(19) 0.0038(18) C16 0.0388(16) 0.0516(17) 0.0480(17) -0.0021(13) -0.0028(13) 0.0044(13) C17 0.060(2) 0.0501(16) 0.0461(16) 0.0010(13) -0.0021(15) 0.0028(15) C18 0.075(3) 0.077(2) 0.075(2) -0.006(2) -0.0028(19) -0.018(2) C19 0.132(4) 0.080(3) 0.084(3) -0.005(2) -0.018(3) -0.039(3) C20 0.191(6) 0.059(2) 0.071(3) -0.013(2) -0.037(3) 0.005(3) C21 0.139(4) 0.084(3) 0.058(2) -0.010(2) -0.007(2) 0.049(3) C22 0.075(2) 0.073(2) 0.0599(19) -0.0049(18) -0.0023(18) 0.0172(18) C23 0.0543(19) 0.0527(17) 0.0457(17) -0.0012(13) 0.0007(14) 0.0069(14) C24 0.095(3) 0.061(2) 0.055(2) 0.0018(15) -0.0072(18) 0.0045(18) C25 0.135(4) 0.072(2) 0.059(2) 0.0170(19) -0.009(2) 0.009(2) C26 0.138(4) 0.056(2) 0.081(3) 0.017(2) 0.003(3) 0.014(2) C27 0.136(4) 0.056(2) 0.077(2) -0.0004(18) -0.001(2) 0.006(2) C28 0.094(3) 0.0570(19) 0.0563(19) 0.0024(16) -0.0055(17) 0.0075(19) _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 C4 1.183(4) . ? O2 C4 1.323(4) . ? O2 C5 1.457(5) . ? O3 C6 1.181(3) . ? O4 C6 1.320(4) . ? O4 C7 1.457(5) . ? O5 C8 1.192(4) . ? O6 C8 1.344(4) . ? O6 C9 1.461(5) . ? N1 C16 1.271(3) . ? N1 C1 1.458(3) . ? C1 C8 1.495(4) . ? C1 C2 1.559(4) . ? C1 H1 0.9800 . ? C2 C10 1.515(4) . ? C2 C3 1.550(4) . ? C2 H2 0.9800 . ? C3 C6 1.514(4) . ? C3 C4 1.523(4) . ? C3 H3 0.9800 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.373(4) . ? C10 C15 1.387(4) . ? C11 C12 1.380(5) . ? C11 H11 0.9300 . ? C12 C13 1.347(6) . ? C12 H12 0.9300 . ? C13 C14 1.360(6) . ? C13 H13 0.9300 . ? C14 C15 1.370(5) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C17 1.489(4) . ? C16 C23 1.496(4) . ? C17 C22 1.380(4) . ? C17 C18 1.382(4) . ? C18 C19 1.378(5) . ? C18 H18 0.9300 . ? C19 C20 1.352(7) . ? C19 H19 0.9300 . ? C20 C21 1.359(6) . ? C20 H20 0.9300 . ? C21 C22 1.392(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 C24 1.365(4) . ? C23 C28 1.378(4) . ? C24 C25 1.381(4) . ? C24 H24 0.9300 . ? C25 C26 1.362(5) . ? C25 H25 0.9300 . ? C26 C27 1.371(5) . ? C26 H26 0.9300 . ? C27 C28 1.366(4) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? 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 C4 O2 C5 114.7(3) . . ? C6 O4 C7 116.0(3) . . ? C8 O6 C9 116.1(3) . . ? C16 N1 C1 119.8(2) . . ? N1 C1 C8 111.5(3) . . ? N1 C1 C2 108.7(2) . . ? C8 C1 C2 112.5(2) . . ? N1 C1 H1 108.0 . . ? C8 C1 H1 108.0 . . ? C2 C1 H1 108.0 . . ? C10 C2 C3 111.4(2) . . ? C10 C2 C1 110.3(2) . . ? C3 C2 C1 112.2(2) . . ? C10 C2 H2 107.6 . . ? C3 C2 H2 107.6 . . ? C1 C2 H2 107.6 . . ? C6 C3 C4 108.3(2) . . ? C6 C3 C2 109.0(2) . . ? C4 C3 C2 112.1(2) . . ? C6 C3 H3 109.1 . . ? C4 C3 H3 109.1 . . ? C2 C3 H3 109.1 . . ? O1 C4 O2 124.8(3) . . ? O1 C4 C3 125.3(3) . . ? O2 C4 C3 109.9(3) . . ? O2 C5 H5A 109.5 . . ? O2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O3 C6 O4 123.7(3) . . ? O3 C6 C3 125.0(3) . . ? O4 C6 C3 111.3(3) . . ? O4 C7 H7A 109.5 . . ? O4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C8 O6 124.4(3) . . ? O5 C8 C1 126.2(3) . . ? O6 C8 C1 109.4(3) . . ? O6 C9 H9A 109.5 . . ? O6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 117.6(3) . . ? C11 C10 C2 120.0(3) . . ? C15 C10 C2 122.4(3) . . ? C10 C11 C12 120.6(4) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 120.9(4) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.6(4) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 120.4(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C10 120.9(4) . . ? C14 C15 H15 119.5 . . ? C10 C15 H15 119.5 . . ? N1 C16 C17 124.7(2) . . ? N1 C16 C23 117.8(2) . . ? C17 C16 C23 117.5(2) . . ? C22 C17 C18 119.1(3) . . ? C22 C17 C16 121.1(3) . . ? C18 C17 C16 119.7(3) . . ? C19 C18 C17 120.1(4) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 120.1(4) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 121.1(4) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C22 119.6(4) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C17 C22 C21 119.9(4) . . ? C17 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C24 C23 C28 117.9(3) . . ? C24 C23 C16 122.0(3) . . ? C28 C23 C16 120.0(2) . . ? C23 C24 C25 121.3(3) . . ? C23 C24 H24 119.3 . . ? C25 C24 H24 119.3 . . ? C26 C25 C24 119.8(3) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C25 C26 C27 119.7(3) . . ? C25 C26 H26 120.1 . . ? C27 C26 H26 120.1 . . ? C28 C27 C26 120.0(3) . . ? C28 C27 H27 120.0 . . ? C26 C27 H27 120.0 . . ? C27 C28 C23 121.2(3) . . ? C27 C28 H28 119.4 . . ? C23 C28 H28 119.4 . . ? 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 C16 N1 C1 C8 -92.9(3) . . . . ? C16 N1 C1 C2 142.6(3) . . . . ? N1 C1 C2 C10 -76.0(3) . . . . ? C8 C1 C2 C10 160.0(3) . . . . ? N1 C1 C2 C3 48.8(3) . . . . ? C8 C1 C2 C3 -75.2(3) . . . . ? C10 C2 C3 C6 -49.2(3) . . . . ? C1 C2 C3 C6 -173.4(2) . . . . ? C10 C2 C3 C4 -169.0(2) . . . . ? C1 C2 C3 C4 66.7(3) . . . . ? C5 O2 C4 O1 -2.7(5) . . . . ? C5 O2 C4 C3 178.9(3) . . . . ? C6 C3 C4 O1 -83.8(4) . . . . ? C2 C3 C4 O1 36.5(4) . . . . ? C6 C3 C4 O2 94.6(3) . . . . ? C2 C3 C4 O2 -145.1(3) . . . . ? C7 O4 C6 O3 4.0(5) . . . . ? C7 O4 C6 C3 -174.7(3) . . . . ? C4 C3 C6 O3 55.4(4) . . . . ? C2 C3 C6 O3 -66.8(4) . . . . ? C4 C3 C6 O4 -125.9(3) . . . . ? C2 C3 C6 O4 112.0(3) . . . . ? C9 O6 C8 O5 -7.8(5) . . . . ? C9 O6 C8 C1 173.6(3) . . . . ? N1 C1 C8 O5 -8.5(5) . . . . ? C2 C1 C8 O5 113.9(4) . . . . ? N1 C1 C8 O6 170.0(2) . . . . ? C2 C1 C8 O6 -67.6(3) . . . . ? C3 C2 C10 C11 128.9(3) . . . . ? C1 C2 C10 C11 -105.8(3) . . . . ? C3 C2 C10 C15 -52.9(4) . . . . ? C1 C2 C10 C15 72.3(3) . . . . ? C15 C10 C11 C12 1.8(5) . . . . ? C2 C10 C11 C12 -180.0(3) . . . . ? C10 C11 C12 C13 -1.0(6) . . . . ? C11 C12 C13 C14 0.3(7) . . . . ? C12 C13 C14 C15 -0.4(7) . . . . ? C13 C14 C15 C10 1.3(6) . . . . ? C11 C10 C15 C14 -1.9(5) . . . . ? C2 C10 C15 C14 179.8(3) . . . . ? C1 N1 C16 C17 4.7(4) . . . . ? C1 N1 C16 C23 -175.1(3) . . . . ? N1 C16 C17 C22 -92.6(4) . . . . ? C23 C16 C17 C22 87.2(3) . . . . ? N1 C16 C17 C18 86.5(4) . . . . ? C23 C16 C17 C18 -93.7(3) . . . . ? C22 C17 C18 C19 0.3(5) . . . . ? C16 C17 C18 C19 -178.8(3) . . . . ? C17 C18 C19 C20 0.1(6) . . . . ? C18 C19 C20 C21 0.0(6) . . . . ? C19 C20 C21 C22 -0.5(6) . . . . ? C18 C17 C22 C21 -0.8(4) . . . . ? C16 C17 C22 C21 178.3(3) . . . . ? C20 C21 C22 C17 0.9(5) . . . . ? N1 C16 C23 C24 -175.7(3) . . . . ? C17 C16 C23 C24 4.5(4) . . . . ? N1 C16 C23 C28 7.1(4) . . . . ? C17 C16 C23 C28 -172.7(3) . . . . ? C28 C23 C24 C25 -1.0(5) . . . . ? C16 C23 C24 C25 -178.3(3) . . . . ? C23 C24 C25 C26 -0.2(6) . . . . ? C24 C25 C26 C27 1.5(7) . . . . ? C25 C26 C27 C28 -1.4(7) . . . . ? C26 C27 C28 C23 0.2(6) . . . . ? C24 C23 C28 C27 1.1(5) . . . . ? C16 C23 C28 C27 178.4(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.114 _refine_diff_density_min -0.111 _refine_diff_density_rms 0.023