# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Wu, Yan-Chao' _publ_contact_author_email ycwu@iccas.ac.cn _publ_section_title ; Cascade reaction of b,g-unsaturated a-ketoesters with phenols in trityl chloride/TFA system. Highly selective synthesis of 4-aryl-2H-chromenes and their applications ; loop_ _publ_author_name 'Yan-Chao Wu' 'Hui-Jing Li' 'Li Liu' 'Zhe Liu' 'Dong Wang' 'Yong-Jun Chen' data_13a _database_code_depnum_ccdc_archive 'CCDC 791782' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 O3' _chemical_formula_weight 322.39 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' 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 17.683(4) _cell_length_b 10.819(2) _cell_length_c 10.206(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.81(3) _cell_angle_gamma 90.00 _cell_volume 1772.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6608 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9551 _exptl_absorpt_correction_T_max 0.9881 _exptl_absorpt_process_details abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis Rapid IP' _diffrn_measurement_method oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6608 _diffrn_reflns_av_R_equivalents 0.0799 _diffrn_reflns_av_sigmaI/netI 0.0706 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1990 _reflns_number_gt 1363 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid Auto(Rigaku 2001)' _computing_cell_refinement 'Rapid Auto(Rigaku 2001)' _computing_data_reduction 'Rapid Auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1002P)^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 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 1(2) _refine_ls_number_reflns 1990 _refine_ls_number_parameters 217 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0905 _refine_ls_R_factor_gt 0.0698 _refine_ls_wR_factor_ref 0.1823 _refine_ls_wR_factor_gt 0.1715 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.1799(2) 0.4764(4) 0.8023(5) 0.1066(16) Uani 1 1 d . . . O2 O 0.2393(2) 0.3433(4) 0.9860(4) 0.0775(10) Uani 1 1 d . . . O3 O 0.38337(18) 0.3658(3) 0.9846(3) 0.0614(9) Uani 1 1 d . . . C1 C 0.1586(4) 0.3263(7) 0.9882(8) 0.100(2) Uani 1 1 d . . . H1A H 0.1628 0.2651 1.0590 0.149 Uiso 1 1 calc R . . H1B H 0.1191 0.2995 0.8948 0.149 Uiso 1 1 calc R . . H1C H 0.1403 0.4031 1.0123 0.149 Uiso 1 1 calc R . . C2 C 0.2401(3) 0.4274(5) 0.8902(6) 0.0680(14) Uani 1 1 d . . . C3 C 0.3252(2) 0.4487(4) 0.8968(4) 0.0500(10) Uani 1 1 d . . . C4 C 0.3406(3) 0.5375(4) 0.8295(5) 0.0580(10) Uani 1 1 d . . . H4A H 0.2959 0.5832 0.7652 0.070 Uiso 1 1 calc R . . C5 C 0.4257(2) 0.5725(4) 0.8478(4) 0.0502(9) Uani 1 1 d . . . H5A H 0.4247 0.5828 0.7517 0.060 Uiso 1 1 calc R . . C6 C 0.4487(2) 0.6982(3) 0.9269(5) 0.0450(9) Uani 1 1 d . . . C7 C 0.4297(3) 0.8058(4) 0.8473(6) 0.0625(12) Uani 1 1 d . . . H7A H 0.4055 0.8037 0.7469 0.075 Uiso 1 1 calc R . . C8 C 0.4477(4) 0.9184(4) 0.9216(8) 0.0810(18) Uani 1 1 d . . . H8A H 0.4354 0.9919 0.8697 0.097 Uiso 1 1 calc R . . C9 C 0.4832(3) 0.9223(5) 1.0692(7) 0.0781(16) Uani 1 1 d . . . H9A H 0.4958 0.9978 1.1172 0.094 Uiso 1 1 calc R . . C10 C 0.5002(3) 0.8120(5) 1.1469(7) 0.0757(14) Uani 1 1 d . . . H10A H 0.5230 0.8132 1.2473 0.091 Uiso 1 1 calc R . . C11 C 0.4833(3) 0.7036(4) 1.0754(5) 0.0579(11) Uani 1 1 d . . . H11A H 0.4952 0.6303 1.1278 0.069 Uiso 1 1 calc R . . C12 C 0.4855(2) 0.4716(3) 0.9235(4) 0.0435(8) Uani 1 1 d . . . C13 C 0.4630(3) 0.3761(3) 0.9880(4) 0.0483(9) Uani 1 1 d . . . C14 C 0.5178(3) 0.2826(4) 1.0614(5) 0.0609(11) Uani 1 1 d . . . H14A H 0.5014 0.2197 1.1060 0.073 Uiso 1 1 calc R . . C15 C 0.5963(3) 0.2844(4) 1.0674(6) 0.0608(12) Uani 1 1 d . . . H15A H 0.6330 0.2211 1.1155 0.073 Uiso 1 1 calc R . . C16 C 0.6236(2) 0.3797(4) 1.0026(4) 0.0513(10) Uani 1 1 d . . . C17 C 0.5664(2) 0.4702(4) 0.9322(4) 0.0480(9) Uani 1 1 d . . . H17A H 0.5825 0.5339 0.8880 0.058 Uiso 1 1 calc R . . C18 C 0.7111(3) 0.3784(5) 1.0063(5) 0.0652(13) Uani 1 1 d . . . C19 C 0.7702(5) 0.3007(13) 1.1284(13) 0.213(7) Uani 1 1 d . . . H19A H 0.8243 0.3020 1.1275 0.320 Uiso 1 1 calc R . . H19B H 0.7501 0.2172 1.1172 0.320 Uiso 1 1 calc R . . H19C H 0.7741 0.3332 1.2185 0.320 Uiso 1 1 calc R . . C20 C 0.7072(5) 0.3278(11) 0.8667(12) 0.162(5) Uani 1 1 d . . . H20A H 0.7621 0.3272 0.8693 0.242 Uiso 1 1 calc R . . H20B H 0.6714 0.3788 0.7882 0.242 Uiso 1 1 calc R . . H20C H 0.6857 0.2451 0.8532 0.242 Uiso 1 1 calc R . . C21 C 0.7462(5) 0.5068(7) 1.0195(14) 0.155(4) Uani 1 1 d . . . H21A H 0.8009 0.5027 1.0215 0.233 Uiso 1 1 calc R . . H21B H 0.7494 0.5441 1.1071 0.233 Uiso 1 1 calc R . . H21C H 0.7106 0.5555 0.9384 0.233 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 0.0362(18) 0.097(3) 0.153(4) 0.032(3) 0.007(2) 0.0029(18) O2 0.0473(18) 0.109(3) 0.080(2) -0.004(2) 0.0306(17) -0.0103(19) O3 0.0452(15) 0.079(2) 0.066(2) 0.0176(16) 0.0287(15) 0.0076(14) C1 0.059(3) 0.137(5) 0.117(5) -0.011(4) 0.051(4) -0.016(3) C2 0.050(3) 0.067(3) 0.085(4) -0.010(3) 0.026(3) -0.007(2) C3 0.036(2) 0.056(2) 0.049(2) -0.0062(19) 0.0096(17) -0.0016(16) C4 0.040(2) 0.057(2) 0.063(3) 0.002(2) 0.0077(19) 0.0043(17) C5 0.046(2) 0.057(2) 0.043(2) 0.0063(18) 0.0145(18) 0.0034(17) C6 0.0345(17) 0.0432(19) 0.061(2) 0.0104(17) 0.0237(18) 0.0083(14) C7 0.052(3) 0.063(3) 0.080(3) 0.021(2) 0.035(2) 0.010(2) C8 0.075(3) 0.046(2) 0.138(6) 0.021(3) 0.061(4) 0.013(2) C9 0.063(3) 0.055(3) 0.116(5) -0.013(3) 0.038(3) -0.003(2) C10 0.065(3) 0.076(4) 0.078(3) -0.014(3) 0.022(3) 0.006(2) C11 0.055(2) 0.048(2) 0.064(3) 0.003(2) 0.019(2) 0.0032(17) C12 0.0413(19) 0.049(2) 0.041(2) -0.0042(17) 0.0187(16) 0.0013(16) C13 0.045(2) 0.052(2) 0.055(3) -0.0019(19) 0.028(2) 0.0041(17) C14 0.059(3) 0.055(2) 0.077(3) 0.013(2) 0.037(2) 0.0084(19) C15 0.059(3) 0.049(2) 0.078(3) 0.012(2) 0.032(2) 0.0180(19) C16 0.040(2) 0.062(2) 0.054(3) -0.0078(19) 0.0226(19) 0.0071(17) C17 0.048(2) 0.047(2) 0.054(2) 0.0025(17) 0.026(2) 0.0018(16) C18 0.043(2) 0.085(3) 0.070(3) -0.007(3) 0.026(2) 0.006(2) C19 0.059(5) 0.330(17) 0.254(14) 0.170(13) 0.068(7) 0.060(7) C20 0.088(5) 0.261(12) 0.176(9) -0.089(9) 0.094(6) -0.028(7) C21 0.074(4) 0.105(5) 0.312(14) -0.047(7) 0.105(7) -0.027(4) _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 C2 1.192(7) . ? O2 C2 1.340(6) . ? O2 C1 1.448(6) . ? O3 C3 1.375(5) . ? O3 C13 1.398(5) . ? C2 C3 1.495(6) . ? C3 C4 1.275(6) . ? C4 C5 1.485(6) . ? C5 C12 1.490(6) . ? C5 C6 1.546(6) . ? C6 C11 1.377(6) . ? C6 C7 1.378(5) . ? C7 C8 1.399(8) . ? C8 C9 1.368(8) . ? C9 C10 1.395(8) . ? C10 C11 1.347(7) . ? C12 C13 1.371(5) . ? C12 C17 1.397(5) . ? C13 C14 1.384(6) . ? C14 C15 1.364(6) . ? C15 C16 1.415(6) . ? C16 C17 1.375(5) . ? C16 C18 1.531(6) . ? C18 C20 1.502(10) . ? C18 C19 1.503(10) . ? C18 C21 1.504(9) . ? 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 O2 C1 114.3(4) . . ? C3 O3 C13 115.8(3) . . ? O1 C2 O2 124.8(5) . . ? O1 C2 C3 122.0(5) . . ? O2 C2 C3 113.0(4) . . ? C4 C3 O3 124.9(3) . . ? C4 C3 C2 122.0(4) . . ? O3 C3 C2 113.1(4) . . ? C3 C4 C5 123.9(4) . . ? C4 C5 C12 109.9(3) . . ? C4 C5 C6 108.7(3) . . ? C12 C5 C6 113.5(3) . . ? C11 C6 C7 119.9(4) . . ? C11 C6 C5 120.7(3) . . ? C7 C6 C5 119.3(4) . . ? C6 C7 C8 118.2(5) . . ? C9 C8 C7 121.3(5) . . ? C8 C9 C10 119.3(5) . . ? C11 C10 C9 119.4(5) . . ? C10 C11 C6 121.9(4) . . ? C13 C12 C17 117.2(3) . . ? C13 C12 C5 121.0(3) . . ? C17 C12 C5 121.8(3) . . ? C12 C13 C14 122.2(4) . . ? C12 C13 O3 122.7(3) . . ? C14 C13 O3 115.1(3) . . ? C15 C14 C13 118.8(4) . . ? C14 C15 C16 122.0(4) . . ? C17 C16 C15 116.3(3) . . ? C17 C16 C18 122.2(4) . . ? C15 C16 C18 121.4(4) . . ? C16 C17 C12 123.4(4) . . ? C20 C18 C19 108.8(7) . . ? C20 C18 C21 105.9(7) . . ? C19 C18 C21 109.0(8) . . ? C20 C18 C16 109.7(5) . . ? C19 C18 C16 111.7(5) . . ? C21 C18 C16 111.6(4) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.307 _refine_diff_density_min -0.303 _refine_diff_density_rms 0.055 data_3a _database_code_depnum_ccdc_archive 'CCDC 791783' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 O4' _chemical_formula_weight 338.39 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' 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.3688(8) _cell_length_b 7.7163(4) _cell_length_c 18.1469(11) _cell_angle_alpha 90.00 _cell_angle_beta 111.567(2) _cell_angle_gamma 90.00 _cell_volume 1871.15(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.78 _exptl_crystal_size_mid 0.73 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9382 _exptl_absorpt_correction_T_max 0.9733 _exptl_absorpt_process_details 'Psi scan' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku R-axis RAPID IP' _diffrn_measurement_method Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3958 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1574 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3958 _reflns_number_gt 1238 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID AUTO (Rigaku, 2001)' _computing_cell_refinement 'RAPID AUTO (Rigaku, 2001)' _computing_data_reduction 'RAPID AUTO (Rigaku, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Siemens, 1994)' _computing_publication_material 'SHELXTL (Siemens, 1994)' _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^)+(0.0600P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3958 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1399 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1209 _refine_ls_goodness_of_fit_ref 0.673 _refine_ls_restrained_S_all 0.673 _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 0.00143(17) 0.6975(3) 0.04171(13) 0.0825(7) Uani 1 1 d . . . O2 O 0.01757(15) 0.8291(3) 0.15401(11) 0.0715(6) Uani 1 1 d . . . O3 O -0.03921(14) 0.3926(2) 0.09552(11) 0.0664(6) Uani 1 1 d . . . H3A H -0.0143 0.4030 0.0617 0.100 Uiso 1 1 calc R . . O4 O 0.09379(13) 0.4988(2) 0.20233(11) 0.0595(5) Uani 1 1 d . . . C1 C 0.0354(3) 0.9936(3) 0.1217(2) 0.0907(11) Uani 1 1 d . . . H1A H 0.0444 1.0837 0.1602 0.136 Uiso 1 1 calc R . . H1B H -0.0209 1.0209 0.0746 0.136 Uiso 1 1 calc R . . H1C H 0.0945 0.9845 0.1091 0.136 Uiso 1 1 calc R . . C2 C 0.00377(19) 0.6941(4) 0.10773(18) 0.0540(7) Uani 1 1 d . . . C3 C -0.0075(2) 0.5268(3) 0.14920(16) 0.0498(7) Uani 1 1 d . . . C4 C -0.07650(18) 0.5382(3) 0.19410(15) 0.0497(7) Uani 1 1 d . . . H4B H -0.1309 0.6132 0.1765 0.060 Uiso 1 1 calc R . . C5 C -0.06151(18) 0.4436(3) 0.25843(16) 0.0464(7) Uani 1 1 d . . . C6 C -0.13240(18) 0.4527(3) 0.30064(17) 0.0475(7) Uani 1 1 d . . . C7 C -0.2350(2) 0.4439(4) 0.25856(19) 0.0635(8) Uani 1 1 d . . . H7A H -0.2594 0.4204 0.2045 0.076 Uiso 1 1 calc R . . C8 C -0.3012(2) 0.4705(4) 0.2977(2) 0.0790(10) Uani 1 1 d . . . H8A H -0.3697 0.4645 0.2691 0.095 Uiso 1 1 calc R . . C9 C -0.2684(3) 0.5045(4) 0.3760(2) 0.0807(10) Uani 1 1 d . . . H9A H -0.3137 0.5236 0.4009 0.097 Uiso 1 1 calc R . . C10 C -0.1675(3) 0.5106(4) 0.41835(19) 0.0753(9) Uani 1 1 d . . . H10A H -0.1439 0.5333 0.4725 0.090 Uiso 1 1 calc R . . C11 C -0.1005(2) 0.4833(3) 0.38090(17) 0.0603(8) Uani 1 1 d . . . H11A H -0.0322 0.4856 0.4107 0.072 Uiso 1 1 calc R . . C12 C 0.02982(18) 0.3381(3) 0.28822(15) 0.0466(7) Uani 1 1 d . . . C13 C 0.1055(2) 0.3706(3) 0.25910(16) 0.0521(7) Uani 1 1 d . . . C14 C 0.1948(2) 0.2825(4) 0.28588(17) 0.0649(8) Uani 1 1 d . . . H14A H 0.2456 0.3115 0.2679 0.078 Uiso 1 1 calc R . . C15 C 0.2080(2) 0.1497(4) 0.34008(17) 0.0646(8) Uani 1 1 d . . . H15A H 0.2682 0.0895 0.3582 0.078 Uiso 1 1 calc R . . C16 C 0.13300(19) 0.1039(4) 0.36827(16) 0.0534(7) Uani 1 1 d . . . C17 C 0.04555(18) 0.2015(3) 0.34197(15) 0.0519(7) Uani 1 1 d . . . H17A H -0.0046 0.1747 0.3610 0.062 Uiso 1 1 calc R . . C18 C 0.1461(2) -0.0501(4) 0.42421(17) 0.0608(8) Uani 1 1 d . . . C19 C 0.2255(5) -0.1708(7) 0.4213(4) 0.272(4) Uani 1 1 d . . . H19A H 0.2312 -0.2661 0.4567 0.408 Uiso 1 1 calc R . . H19B H 0.2882 -0.1104 0.4369 0.408 Uiso 1 1 calc R . . H19C H 0.2082 -0.2139 0.3683 0.408 Uiso 1 1 calc R . . C20 C 0.0546(3) -0.1486(6) 0.4054(3) 0.211(3) Uani 1 1 d . . . H20A H 0.0655 -0.2432 0.4420 0.317 Uiso 1 1 calc R . . H20B H 0.0347 -0.1930 0.3525 0.317 Uiso 1 1 calc R . . H20C H 0.0028 -0.0749 0.4094 0.317 Uiso 1 1 calc R . . C21 C 0.1772(4) 0.0115(5) 0.5062(2) 0.194(3) Uani 1 1 d . . . H21A H 0.1842 -0.0855 0.5409 0.291 Uiso 1 1 calc R . . H21D H 0.1276 0.0896 0.5108 0.291 Uiso 1 1 calc R . . H21B H 0.2401 0.0708 0.5204 0.291 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 0.1391(19) 0.0611(13) 0.0601(14) 0.0065(12) 0.0518(14) -0.0055(13) O2 0.1097(17) 0.0454(11) 0.0645(14) -0.0005(11) 0.0383(12) -0.0065(11) O3 0.0955(15) 0.0485(11) 0.0656(13) -0.0014(11) 0.0418(11) -0.0062(11) O4 0.0512(11) 0.0635(12) 0.0686(14) 0.0197(11) 0.0277(11) 0.0039(10) C1 0.124(3) 0.0421(18) 0.110(3) 0.0107(19) 0.048(2) -0.013(2) C2 0.0577(18) 0.0494(18) 0.059(2) 0.0031(18) 0.0258(17) -0.0034(15) C3 0.0583(18) 0.0444(16) 0.0467(17) 0.0043(15) 0.0196(15) -0.0001(15) C4 0.0473(16) 0.0498(16) 0.0514(17) 0.0020(15) 0.0175(14) 0.0030(14) C5 0.0436(15) 0.0468(16) 0.0492(17) -0.0001(15) 0.0176(14) -0.0010(14) C6 0.0415(16) 0.0481(16) 0.0531(18) 0.0065(14) 0.0176(14) 0.0020(14) C7 0.0491(17) 0.073(2) 0.068(2) 0.0121(17) 0.0210(16) -0.0016(17) C8 0.0475(17) 0.103(3) 0.090(3) 0.020(2) 0.030(2) 0.0024(19) C9 0.069(2) 0.100(3) 0.087(3) 0.021(2) 0.045(2) 0.013(2) C10 0.088(2) 0.081(2) 0.064(2) 0.0048(19) 0.036(2) 0.008(2) C11 0.0526(16) 0.072(2) 0.060(2) 0.0031(17) 0.0252(16) 0.0006(17) C12 0.0458(15) 0.0461(16) 0.0470(16) 0.0053(14) 0.0161(13) 0.0012(14) C13 0.0532(18) 0.0486(17) 0.0551(19) 0.0077(15) 0.0205(15) -0.0026(15) C14 0.0478(17) 0.072(2) 0.078(2) 0.0137(19) 0.0271(16) 0.0061(17) C15 0.0529(17) 0.068(2) 0.076(2) 0.0172(18) 0.0279(17) 0.0178(17) C16 0.0491(17) 0.0553(17) 0.0528(18) 0.0072(15) 0.0150(14) 0.0085(15) C17 0.0505(16) 0.0556(17) 0.0534(18) 0.0055(15) 0.0235(14) 0.0045(15) C18 0.0596(18) 0.0606(18) 0.058(2) 0.0185(16) 0.0173(15) 0.0112(17) C19 0.391(9) 0.183(5) 0.397(9) 0.218(6) 0.329(8) 0.217(6) C20 0.134(4) 0.155(4) 0.243(6) 0.148(4) -0.049(4) -0.071(4) C21 0.314(7) 0.137(4) 0.065(3) 0.042(3) -0.007(4) -0.062(4) _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 C2 1.186(3) . ? O2 C2 1.307(3) . ? O2 C1 1.460(3) . ? O3 C3 1.379(3) . ? O3 H3A 0.8200 . ? O4 C13 1.393(3) . ? O4 C3 1.436(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.532(4) . ? C3 C4 1.500(3) . ? C4 C5 1.325(3) . ? C4 H4B 0.9300 . ? C5 C12 1.468(3) . ? C5 C6 1.484(3) . ? C6 C11 1.377(3) . ? C6 C7 1.390(3) . ? C7 C8 1.397(4) . ? C7 H7A 0.9300 . ? C8 C9 1.347(4) . ? C8 H8A 0.9300 . ? C9 C10 1.370(4) . ? C9 H9A 0.9300 . ? C10 C11 1.383(4) . ? C10 H10A 0.9300 . ? C11 H11A 0.9300 . ? C12 C13 1.395(3) . ? C12 C17 1.397(3) . ? C13 C14 1.373(3) . ? C14 C15 1.384(3) . ? C14 H14A 0.9300 . ? C15 C16 1.397(3) . ? C15 H15A 0.9300 . ? C16 C17 1.390(3) . ? C16 C18 1.529(4) . ? C17 H17A 0.9300 . ? C18 C20 1.447(4) . ? C18 C21 1.466(4) . ? C18 C19 1.489(5) . ? 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 H21D 0.9600 . ? C21 H21B 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 C2 O2 C1 116.3(2) . . ? C3 O3 H3A 109.5 . . ? C13 O4 C3 114.84(19) . . ? O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 O2 124.9(3) . . ? O1 C2 C3 123.1(3) . . ? O2 C2 C3 112.0(2) . . ? O3 C3 O4 110.6(2) . . ? O3 C3 C4 108.4(2) . . ? O4 C3 C4 110.7(2) . . ? O3 C3 C2 110.6(2) . . ? O4 C3 C2 101.1(2) . . ? C4 C3 C2 115.3(2) . . ? C5 C4 C3 121.3(2) . . ? C5 C4 H4B 119.3 . . ? C3 C4 H4B 119.3 . . ? C4 C5 C12 117.6(2) . . ? C4 C5 C6 120.6(2) . . ? C12 C5 C6 121.7(2) . . ? C11 C6 C7 117.6(3) . . ? C11 C6 C5 122.0(2) . . ? C7 C6 C5 120.3(3) . . ? C6 C7 C8 119.8(3) . . ? C6 C7 H7A 120.1 . . ? C8 C7 H7A 120.1 . . ? C9 C8 C7 121.7(3) . . ? C9 C8 H8A 119.2 . . ? C7 C8 H8A 119.2 . . ? C8 C9 C10 119.1(3) . . ? C8 C9 H9A 120.4 . . ? C10 C9 H9A 120.4 . . ? C9 C10 C11 120.2(3) . . ? C9 C10 H10A 119.9 . . ? C11 C10 H10A 119.9 . . ? C6 C11 C10 121.6(3) . . ? C6 C11 H11A 119.2 . . ? C10 C11 H11A 119.2 . . ? C13 C12 C17 116.8(2) . . ? C13 C12 C5 118.5(2) . . ? C17 C12 C5 124.7(2) . . ? C14 C13 O4 117.2(2) . . ? C14 C13 C12 122.3(3) . . ? O4 C13 C12 120.6(2) . . ? C13 C14 C15 119.0(3) . . ? C13 C14 H14A 120.5 . . ? C15 C14 H14A 120.5 . . ? C14 C15 C16 121.7(3) . . ? C14 C15 H15A 119.2 . . ? C16 C15 H15A 119.2 . . ? C17 C16 C15 117.3(3) . . ? C17 C16 C18 121.6(3) . . ? C15 C16 C18 121.1(2) . . ? C16 C17 C12 122.8(3) . . ? C16 C17 H17A 118.6 . . ? C12 C17 H17A 118.6 . . ? C20 C18 C21 108.7(4) . . ? C20 C18 C19 107.7(4) . . ? C21 C18 C19 106.7(4) . . ? C20 C18 C16 111.9(3) . . ? C21 C18 C16 109.8(3) . . ? C19 C18 C16 111.8(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 H21D 109.5 . . ? H21A C21 H21D 109.5 . . ? C18 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? H21D C21 H21B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.322 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.041 data_6a _database_code_depnum_ccdc_archive 'CCDC 791784' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H29 N O3' _chemical_formula_weight 427.52 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 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 6.0368(12) _cell_length_b 13.398(3) _cell_length_c 29.789(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2409.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18931 _cell_measurement_theta_min 1.37 _cell_measurement_theta_max 27.47 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9455 _exptl_absorpt_correction_T_max 0.9943 _exptl_absorpt_process_details abscor _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Raxis Rapid IP' _diffrn_measurement_method oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18931 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0582 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3133 _reflns_number_gt 2054 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rapid auto(Rigaku 2001)' _computing_cell_refinement 'Rapid auto(Rigaku 2001)' _computing_data_reduction 'Rapid auto(Rigaku 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0619P)^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 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 -1(2) _refine_ls_number_reflns 3133 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1307 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _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 0.1746(4) 0.62376(18) 0.24613(7) 0.0665(6) Uani 1 1 d . . . O2 O 0.4541(3) 0.7217(2) 0.22672(9) 0.0748(7) Uani 1 1 d . . . O3 O 0.1963(3) 0.85279(15) 0.18820(6) 0.0551(6) Uani 1 1 d . . . N1 N -0.0855(4) 0.79798(19) 0.23803(7) 0.0497(6) Uani 1 1 d . . . H1A H -0.2222 0.7940 0.2301 0.060 Uiso 1 1 calc R . . C1 C 0.3279(6) 0.5543(3) 0.26599(13) 0.0821(11) Uani 1 1 d . . . H1B H 0.2476 0.4992 0.2786 0.123 Uiso 1 1 calc R . . H1C H 0.4107 0.5872 0.2892 0.123 Uiso 1 1 calc R . . H1D H 0.4277 0.5301 0.2434 0.123 Uiso 1 1 calc R . . C2 C 0.2611(5) 0.7043(3) 0.22737(9) 0.0500(7) Uani 1 1 d . . . C3 C 0.0783(4) 0.7680(2) 0.20615(9) 0.0457(7) Uani 1 1 d . . . C4 C -0.0370(5) 0.7120(2) 0.16916(9) 0.0473(7) Uani 1 1 d . . . H4A H -0.0498 0.6429 0.1707 0.057 Uiso 1 1 calc R . . C5 C -0.1201(5) 0.7610(2) 0.13453(9) 0.0438(7) Uani 1 1 d . . . C6 C -0.2527(5) 0.7106(2) 0.09888(9) 0.0465(7) Uani 1 1 d . . . C7 C -0.4513(6) 0.6663(3) 0.10917(13) 0.0731(10) Uani 1 1 d . . . H7A H -0.5038 0.6677 0.1385 0.088 Uiso 1 1 calc R . . C8 C -0.5736(7) 0.6193(3) 0.07595(17) 0.0980(14) Uani 1 1 d . . . H8A H -0.7084 0.5895 0.0829 0.118 Uiso 1 1 calc R . . C9 C -0.4962(10) 0.6170(3) 0.03317(17) 0.0978(16) Uani 1 1 d . . . H9A H -0.5793 0.5859 0.0109 0.117 Uiso 1 1 calc R . . C10 C -0.2996(9) 0.6592(3) 0.02257(12) 0.0827(13) Uani 1 1 d . . . H10A H -0.2470 0.6561 -0.0067 0.099 Uiso 1 1 calc R . . C11 C -0.1763(6) 0.7072(2) 0.05542(10) 0.0604(9) Uani 1 1 d . . . H11A H -0.0421 0.7371 0.0480 0.072 Uiso 1 1 calc R . . C12 C -0.0850(5) 0.8698(2) 0.13136(9) 0.0472(7) Uani 1 1 d . . . C13 C -0.2010(5) 0.9316(2) 0.10249(10) 0.0489(7) Uani 1 1 d . . . H13A H -0.3090 0.9038 0.0840 0.059 Uiso 1 1 calc R . . C14 C -0.1614(5) 1.0339(2) 0.10010(10) 0.0517(8) Uani 1 1 d . . . C15 C 0.0042(6) 1.0714(3) 0.12778(11) 0.0652(9) Uani 1 1 d . . . H15A H 0.0373 1.1391 0.1266 0.078 Uiso 1 1 calc R . . C16 C 0.1204(6) 1.0117(2) 0.15682(11) 0.0645(9) Uani 1 1 d . . . H16A H 0.2297 1.0394 0.1750 0.077 Uiso 1 1 calc R . . C17 C 0.0759(5) 0.9112(2) 0.15923(9) 0.0501(7) Uani 1 1 d . . . C18 C -0.2899(6) 1.1035(2) 0.06894(11) 0.0574(8) Uani 1 1 d . . . C19 C -0.4033(7) 1.1854(3) 0.09674(13) 0.0805(11) Uani 1 1 d . . . H19A H -0.2940 1.2207 0.1140 0.121 Uiso 1 1 calc R . . H19B H -0.5095 1.1556 0.1166 0.121 Uiso 1 1 calc R . . H19C H -0.4773 1.2312 0.0770 0.121 Uiso 1 1 calc R . . C20 C -0.1316(7) 1.1523(3) 0.03562(13) 0.0816(11) Uani 1 1 d . . . H20A H -0.0607 1.1016 0.0179 0.122 Uiso 1 1 calc R . . H20B H -0.0214 1.1896 0.0517 0.122 Uiso 1 1 calc R . . H20C H -0.2129 1.1963 0.0163 0.122 Uiso 1 1 calc R . . C21 C -0.4716(7) 1.0494(2) 0.04289(12) 0.0707(10) Uani 1 1 d . . . H21A H -0.4065 0.9979 0.0248 0.106 Uiso 1 1 calc R . . H21B H -0.5477 1.0961 0.0239 0.106 Uiso 1 1 calc R . . H21C H -0.5748 1.0202 0.0636 0.106 Uiso 1 1 calc R . . C22 C -0.0391(5) 0.8334(2) 0.28134(9) 0.0444(7) Uani 1 1 d . . . C23 C 0.1589(5) 0.8786(2) 0.29251(10) 0.0541(8) Uani 1 1 d . . . H23A H 0.2688 0.8865 0.2709 0.065 Uiso 1 1 calc R . . C24 C 0.1931(6) 0.9119(2) 0.33588(10) 0.0561(8) Uani 1 1 d . . . H24A H 0.3277 0.9419 0.3429 0.067 Uiso 1 1 calc R . . C25 C 0.0378(6) 0.9027(2) 0.36882(10) 0.0528(8) Uani 1 1 d . . . C26 C -0.1626(6) 0.8598(2) 0.35687(10) 0.0585(8) Uani 1 1 d . . . H26A H -0.2742 0.8547 0.3783 0.070 Uiso 1 1 calc R . . C27 C -0.2008(5) 0.8243(2) 0.31403(10) 0.0528(8) Uani 1 1 d . . . H27A H -0.3355 0.7943 0.3071 0.063 Uiso 1 1 calc R . . C28 C 0.0802(8) 0.9345(2) 0.41683(10) 0.0744(11) Uani 1 1 d . . . H28A H 0.2266 0.9619 0.4192 0.112 Uiso 1 1 calc R . . H28B H 0.0674 0.8776 0.4363 0.112 Uiso 1 1 calc R . . H28C H -0.0265 0.9840 0.4254 0.112 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 0.0477(12) 0.0755(15) 0.0763(14) 0.0207(12) -0.0088(12) -0.0072(12) O2 0.0332(11) 0.1012(19) 0.0901(17) 0.0075(15) -0.0052(11) -0.0099(13) O3 0.0427(11) 0.0730(13) 0.0496(11) 0.0075(10) -0.0075(10) -0.0227(11) N1 0.0300(11) 0.0729(16) 0.0463(14) -0.0056(12) -0.0036(11) -0.0087(12) C1 0.071(2) 0.086(2) 0.090(3) 0.019(2) -0.013(2) 0.007(2) C2 0.0357(15) 0.074(2) 0.0407(15) -0.0068(15) -0.0008(13) -0.0078(15) C3 0.0344(14) 0.0619(18) 0.0408(15) 0.0005(13) -0.0028(13) -0.0136(14) C4 0.0396(14) 0.0562(16) 0.0459(16) -0.0035(14) -0.0042(14) -0.0130(15) C5 0.0400(14) 0.0514(16) 0.0399(15) -0.0062(13) -0.0019(13) -0.0084(13) C6 0.0500(15) 0.0442(15) 0.0453(16) -0.0039(13) -0.0116(14) -0.0008(14) C7 0.0535(19) 0.091(3) 0.074(2) -0.017(2) -0.0080(19) -0.017(2) C8 0.067(3) 0.107(3) 0.120(4) -0.021(3) -0.031(3) -0.028(3) C9 0.123(4) 0.075(3) 0.095(3) -0.020(2) -0.066(3) -0.004(3) C10 0.130(4) 0.067(2) 0.0509(19) -0.0118(18) -0.031(3) 0.022(3) C11 0.075(2) 0.0592(18) 0.0471(17) 0.0014(15) -0.0122(18) 0.0025(19) C12 0.0444(16) 0.0560(17) 0.0412(15) -0.0030(14) 0.0007(14) -0.0097(15) C13 0.0452(15) 0.0544(18) 0.0472(16) -0.0093(13) -0.0043(15) -0.0077(15) C14 0.0532(17) 0.0528(18) 0.0492(17) -0.0070(14) 0.0058(16) -0.0073(15) C15 0.071(2) 0.0563(19) 0.068(2) 0.0010(17) -0.001(2) -0.0219(19) C16 0.060(2) 0.068(2) 0.066(2) -0.0007(18) -0.0088(18) -0.0321(18) C17 0.0429(16) 0.0648(19) 0.0426(15) 0.0026(14) -0.0009(14) -0.0185(15) C18 0.0591(19) 0.0506(17) 0.0625(18) -0.0048(15) 0.0057(17) 0.0025(16) C19 0.078(3) 0.064(2) 0.100(3) -0.018(2) 0.012(2) 0.004(2) C20 0.087(3) 0.075(2) 0.084(2) 0.021(2) 0.016(2) 0.006(2) C21 0.076(2) 0.069(2) 0.068(2) -0.0044(18) -0.012(2) 0.015(2) C22 0.0394(14) 0.0481(16) 0.0457(16) 0.0017(13) -0.0042(14) -0.0004(14) C23 0.0428(16) 0.0685(19) 0.0511(17) -0.0063(16) -0.0023(15) -0.0115(15) C24 0.0531(17) 0.0563(18) 0.0588(18) -0.0096(15) -0.0097(17) -0.0068(16) C25 0.067(2) 0.0418(16) 0.0492(17) -0.0035(14) -0.0067(17) 0.0071(16) C26 0.064(2) 0.0616(19) 0.0504(18) -0.0003(15) 0.0114(18) -0.0039(18) C27 0.0435(16) 0.0592(18) 0.0558(18) 0.0009(15) 0.0004(15) -0.0078(15) C28 0.103(3) 0.064(2) 0.0558(19) -0.0163(16) -0.011(2) 0.005(2) _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 C2 1.322(4) . ? O1 C1 1.440(4) . ? O2 C2 1.189(3) . ? O3 C17 1.373(3) . ? O3 C3 1.444(3) . ? N1 C22 1.403(3) . ? N1 C3 1.429(3) . ? C2 C3 1.531(4) . ? C3 C4 1.503(4) . ? C4 C5 1.321(4) . ? C5 C12 1.476(4) . ? C5 C6 1.492(4) . ? C6 C7 1.372(5) . ? C6 C11 1.375(4) . ? C7 C8 1.386(5) . ? C8 C9 1.358(7) . ? C9 C10 1.352(7) . ? C10 C11 1.387(5) . ? C12 C13 1.384(4) . ? C12 C17 1.393(4) . ? C13 C14 1.394(4) . ? C14 C15 1.390(4) . ? C14 C18 1.527(4) . ? C15 C16 1.371(5) . ? C16 C17 1.375(4) . ? C18 C20 1.525(5) . ? C18 C21 1.527(5) . ? C18 C19 1.536(4) . ? C22 C23 1.380(4) . ? C22 C27 1.384(4) . ? C23 C24 1.383(4) . ? C24 C25 1.363(5) . ? C25 C26 1.386(5) . ? C25 C28 1.514(4) . ? C26 C27 1.381(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 C2 O1 C1 116.6(2) . . ? C17 O3 C3 114.9(2) . . ? C22 N1 C3 124.6(2) . . ? O2 C2 O1 123.7(3) . . ? O2 C2 C3 126.1(3) . . ? O1 C2 C3 110.2(2) . . ? N1 C3 O3 111.5(2) . . ? N1 C3 C4 107.9(2) . . ? O3 C3 C4 110.5(2) . . ? N1 C3 C2 112.4(2) . . ? O3 C3 C2 103.7(2) . . ? C4 C3 C2 111.0(2) . . ? C5 C4 C3 120.0(3) . . ? C4 C5 C12 119.1(3) . . ? C4 C5 C6 122.3(3) . . ? C12 C5 C6 118.6(2) . . ? C7 C6 C11 119.3(3) . . ? C7 C6 C5 120.4(3) . . ? C11 C6 C5 120.3(3) . . ? C6 C7 C8 120.2(4) . . ? C9 C8 C7 119.8(4) . . ? C10 C9 C8 120.8(4) . . ? C9 C10 C11 120.0(4) . . ? C6 C11 C10 120.0(4) . . ? C13 C12 C17 119.0(3) . . ? C13 C12 C5 123.9(3) . . ? C17 C12 C5 117.1(3) . . ? C12 C13 C14 122.2(3) . . ? C15 C14 C13 116.6(3) . . ? C15 C14 C18 120.4(3) . . ? C13 C14 C18 123.0(3) . . ? C16 C15 C14 122.1(3) . . ? C15 C16 C17 120.3(3) . . ? O3 C17 C16 119.2(3) . . ? O3 C17 C12 121.1(3) . . ? C16 C17 C12 119.7(3) . . ? C20 C18 C21 108.8(3) . . ? C20 C18 C14 109.8(3) . . ? C21 C18 C14 112.6(2) . . ? C20 C18 C19 108.9(3) . . ? C21 C18 C19 107.0(3) . . ? C14 C18 C19 109.6(3) . . ? C23 C22 C27 118.7(3) . . ? C23 C22 N1 122.9(3) . . ? C27 C22 N1 118.5(3) . . ? C22 C23 C24 119.8(3) . . ? C25 C24 C23 122.7(3) . . ? C24 C25 C26 116.9(3) . . ? C24 C25 C28 122.6(3) . . ? C26 C25 C28 120.5(3) . . ? C27 C26 C25 121.7(3) . . ? C26 C27 C22 120.1(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O2 0.86 2.18 2.981(3) 154.0 1_455 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.314 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.122