# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Xue Weijian' _publ_contact_author_email hehexueweijian@163.com loop_ _publ_author_name 'Wei-Jian Xue' 'Qi Li' 'Yan-Ping Zhu' 'Jun-Gang Wang' 'An-Xin Wu' data_110603em _database_code_depnum_ccdc_archive 'CCDC 848144' #TrackingRef 'web_deposit_cif_file_0_XueWeijian_1318329802.110603EM.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H15 N O2' _chemical_formula_weight 325.35 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)/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 17.224(5) _cell_length_b 5.1542(15) _cell_length_c 20.107(6) _cell_angle_alpha 90.00 _cell_angle_beta 113.663(5) _cell_angle_gamma 90.00 _cell_volume 1635.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 857 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 19.24 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9958 _exptl_absorpt_correction_T_max 0.9983 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 29856 _diffrn_reflns_av_R_equivalents 0.0987 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2884 _reflns_number_gt 2123 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0229P)^2^+2.8932P] 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 2884 _refine_ls_number_parameters 263 _refine_ls_number_restraints 22 _refine_ls_R_factor_all 0.1421 _refine_ls_R_factor_gt 0.1073 _refine_ls_wR_factor_ref 0.1765 _refine_ls_wR_factor_gt 0.1659 _refine_ls_goodness_of_fit_ref 1.226 _refine_ls_restrained_S_all 1.230 _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 0.4565(3) 0.9516(9) 0.1183(2) 0.0399(10) Uani 1 1 d . . . C2 C 0.4699(3) 1.1309(9) 0.0726(2) 0.0494(12) Uani 1 1 d . . . H2 H 0.5220 1.1324 0.0689 0.059 Uiso 1 1 calc R . . C3 C 0.4093(3) 1.3055(10) 0.0327(2) 0.0574(13) Uani 1 1 d . . . H3 H 0.4198 1.4215 0.0019 0.069 Uiso 1 1 calc R . . C4 C 0.3322(3) 1.3074(10) 0.0389(2) 0.0577(13) Uani 1 1 d . . . H4 H 0.2903 1.4250 0.0122 0.069 Uiso 1 1 calc R . . C5 C 0.3180(3) 1.1338(10) 0.0848(3) 0.0600(14) Uani 1 1 d . . . H5 H 0.2664 1.1367 0.0895 0.072 Uiso 1 1 calc R . . C6 C 0.3788(3) 0.9557(10) 0.1238(2) 0.0505(12) Uani 1 1 d . . . H6 H 0.3677 0.8378 0.1539 0.061 Uiso 1 1 calc R . . C7 C 0.5268(3) 0.7687(9) 0.1580(2) 0.0437(11) Uani 1 1 d . . . C8 C 0.5210(2) 0.5784(8) 0.2115(2) 0.0381(10) Uani 1 1 d . A . C9 C 0.4935(2) 0.3511(8) 0.2877(2) 0.0359(10) Uani 1 1 d . A . C10 C 0.5691(2) 0.2681(8) 0.2892(2) 0.0362(10) Uani 1 1 d . A . C11 C 0.6322(2) 0.0681(8) 0.3274(2) 0.0364(10) Uani 1 1 d . . . C12 C 0.7080(3) 0.0534(9) 0.3179(2) 0.0467(11) Uani 1 1 d . . . H12 H 0.7189 0.1732 0.2882 0.056 Uiso 1 1 calc R . . C13 C 0.7667(3) -0.1367(9) 0.3521(2) 0.0502(12) Uani 1 1 d . . . H13 H 0.8167 -0.1452 0.3448 0.060 Uiso 1 1 calc R . . C14 C 0.7521(3) -0.3134(9) 0.3967(2) 0.0507(12) Uani 1 1 d . . . H14 H 0.7918 -0.4421 0.4194 0.061 Uiso 1 1 calc R . . C15 C 0.6785(3) -0.2993(9) 0.4077(2) 0.0505(12) Uani 1 1 d . . . H15 H 0.6687 -0.4171 0.4385 0.061 Uiso 1 1 calc R . . C16 C 0.6189(3) -0.1112(9) 0.3732(2) 0.0449(11) Uani 1 1 d . . . H16 H 0.5691 -0.1045 0.3807 0.054 Uiso 1 1 calc R . . C17 C 0.4440(2) 0.2729(8) 0.3302(2) 0.0396(10) Uani 1 1 d D . . C18 C 0.4805(5) 0.2664(19) 0.4049(3) 0.060(2) Uani 0.63 1 d PD A 1 H18 H 0.5379 0.3031 0.4295 0.073 Uiso 0.63 1 calc PR A 1 C19 C 0.4323(5) 0.206(2) 0.4434(4) 0.075(3) Uani 0.63 1 d PD A 1 H19 H 0.4575 0.2070 0.4939 0.091 Uiso 0.63 1 calc PR A 1 C21 C 0.3113(5) 0.156(2) 0.3339(4) 0.088(3) Uani 0.63 1 d PD A 1 H21 H 0.2539 0.1186 0.3095 0.106 Uiso 0.63 1 calc PR A 1 C22 C 0.3590(4) 0.222(2) 0.2949(4) 0.072(3) Uani 0.63 1 d PD A 1 H22 H 0.3332 0.2318 0.2445 0.086 Uiso 0.63 1 calc PR A 1 C20 C 0.3494(4) 0.1441(12) 0.4096(3) 0.0799(19) Uani 1 1 d D . . H20 H 0.3183 0.0953 0.4361 0.096 Uiso 1 1 calc R A 1 C18' C 0.4336(9) 0.448(2) 0.3785(7) 0.071(4) Uani 0.37 1 d PD A 2 H18' H 0.4571 0.6132 0.3830 0.085 Uiso 0.37 1 calc PR A 2 C19' C 0.3888(10) 0.382(2) 0.4199(8) 0.073(5) Uani 0.37 1 d PD A 2 H19' H 0.3855 0.4971 0.4543 0.088 Uiso 0.37 1 calc PR A 2 C21' C 0.3641(9) -0.0416(19) 0.3671(8) 0.067(4) Uani 0.37 1 d PD A 2 H21' H 0.3449 -0.2107 0.3662 0.080 Uiso 0.37 1 calc PR A 2 C22' C 0.4082(7) 0.0288(19) 0.3257(7) 0.052(3) Uani 0.37 1 d PD A 2 H22' H 0.4141 -0.0919 0.2937 0.063 Uiso 0.37 1 calc PR A 2 N1 N 0.4635(2) 0.5486(7) 0.23759(17) 0.0394(9) Uani 1 1 d . . . O1 O 0.5915(2) 0.7687(7) 0.14713(18) 0.0661(11) Uani 1 1 d . . . O2 O 0.58700(16) 0.4125(5) 0.24014(14) 0.0383(7) 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 0.051(3) 0.039(3) 0.029(2) -0.0022(19) 0.015(2) 0.002(2) C2 0.051(3) 0.051(3) 0.046(3) 0.001(2) 0.019(2) 0.000(2) C3 0.071(3) 0.049(3) 0.049(3) 0.010(2) 0.019(3) 0.000(3) C4 0.068(3) 0.052(3) 0.042(3) 0.005(2) 0.011(2) 0.016(3) C5 0.053(3) 0.064(4) 0.060(3) 0.012(3) 0.020(3) 0.019(3) C6 0.052(3) 0.052(3) 0.048(3) 0.008(2) 0.021(2) 0.008(2) C7 0.048(3) 0.047(3) 0.039(2) 0.002(2) 0.020(2) 0.001(2) C8 0.035(2) 0.041(3) 0.036(2) -0.005(2) 0.0118(19) 0.001(2) C9 0.037(2) 0.037(2) 0.034(2) -0.0011(19) 0.0143(19) -0.002(2) C10 0.042(2) 0.038(3) 0.032(2) -0.004(2) 0.0189(19) -0.003(2) C11 0.042(2) 0.033(2) 0.034(2) -0.0071(19) 0.0149(19) -0.005(2) C12 0.050(3) 0.052(3) 0.046(3) 0.007(2) 0.026(2) 0.001(2) C13 0.047(3) 0.051(3) 0.055(3) 0.002(3) 0.023(2) 0.002(2) C14 0.046(3) 0.047(3) 0.049(3) -0.002(2) 0.009(2) 0.002(2) C15 0.056(3) 0.045(3) 0.048(3) 0.009(2) 0.019(2) -0.008(2) C16 0.049(3) 0.043(3) 0.048(3) 0.002(2) 0.025(2) -0.003(2) C17 0.041(2) 0.037(3) 0.047(3) 0.001(2) 0.023(2) 0.002(2) C18 0.062(5) 0.080(7) 0.047(5) -0.006(5) 0.029(4) -0.013(5) C19 0.096(8) 0.088(8) 0.065(6) -0.002(6) 0.055(6) -0.013(7) C21 0.061(6) 0.125(10) 0.101(8) -0.028(7) 0.056(6) -0.026(6) C22 0.048(5) 0.118(9) 0.055(5) 0.002(5) 0.026(4) 0.001(5) C20 0.098(5) 0.077(5) 0.104(5) -0.009(4) 0.081(4) -0.019(4) C18' 0.076(10) 0.053(10) 0.110(12) -0.025(9) 0.064(10) -0.008(9) C19' 0.081(11) 0.064(11) 0.105(13) -0.023(10) 0.070(10) -0.009(10) C21' 0.087(11) 0.037(8) 0.116(12) 0.002(9) 0.081(10) -0.003(8) C22' 0.054(8) 0.041(8) 0.075(9) -0.014(7) 0.041(7) -0.010(7) N1 0.0374(19) 0.045(2) 0.0335(18) 0.0009(17) 0.0117(16) 0.0008(18) O1 0.058(2) 0.080(3) 0.076(2) 0.033(2) 0.0434(19) 0.0222(19) O2 0.0401(16) 0.0407(18) 0.0372(15) 0.0069(14) 0.0186(13) 0.0057(14) _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 C6 1.387(6) . ? C1 C2 1.387(6) . ? C1 C7 1.488(6) . ? C2 C3 1.368(6) . ? C2 H2 0.9300 . ? C3 C4 1.382(6) . ? C3 H3 0.9300 . ? C4 C5 1.376(6) . ? C4 H4 0.9300 . ? C5 C6 1.377(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O1 1.219(5) . ? C7 C8 1.488(6) . ? C8 N1 1.303(5) . ? C8 O2 1.352(5) . ? C9 C10 1.359(5) . ? C9 N1 1.379(5) . ? C9 C17 1.485(5) . ? C10 O2 1.367(4) . ? C10 C11 1.471(6) . ? C11 C16 1.387(5) . ? C11 C12 1.394(5) . ? C12 C13 1.378(6) . ? C12 H12 0.9300 . ? C13 C14 1.371(6) . ? C13 H13 0.9300 . ? C14 C15 1.374(6) . ? C14 H14 0.9300 . ? C15 C16 1.379(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C22 1.373(6) . ? C17 C18 1.376(6) . ? C17 C22' 1.388(8) . ? C17 C18' 1.390(8) . ? C18 C19 1.380(7) . ? C18 H18 0.9300 . ? C19 C20 1.350(7) . ? C19 H19 0.9300 . ? C21 C22 1.386(7) . ? C21 C20 1.396(7) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C20 C21' 1.372(8) . ? C20 C19' 1.377(8) . ? C20 H20 0.9300 . ? C18' C19' 1.385(9) . ? C18' H18' 0.9300 . ? C19' H19' 0.9300 . ? C21' C22' 1.381(8) . ? C21' H21' 0.9300 . ? C22' H22' 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 C6 C1 C2 117.8(4) . . ? C6 C1 C7 124.8(4) . . ? C2 C1 C7 117.4(4) . . ? C3 C2 C1 122.3(4) . . ? C3 C2 H2 118.8 . . ? C1 C2 H2 118.8 . . ? C2 C3 C4 119.2(5) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 119.4(5) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.1(5) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 120.1(5) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O1 C7 C8 117.4(4) . . ? O1 C7 C1 120.7(4) . . ? C8 C7 C1 121.9(4) . . ? N1 C8 O2 113.5(4) . . ? N1 C8 C7 130.6(4) . . ? O2 C8 C7 115.9(3) . . ? C10 C9 N1 108.9(3) . . ? C10 C9 C17 131.9(4) . . ? N1 C9 C17 119.2(3) . . ? C9 C10 O2 107.7(3) . . ? C9 C10 C11 137.2(4) . . ? O2 C10 C11 115.1(3) . . ? C16 C11 C12 117.9(4) . . ? C16 C11 C10 121.9(4) . . ? C12 C11 C10 120.2(4) . . ? C13 C12 C11 120.8(4) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C14 C13 C12 120.5(4) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.6(4) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 120.3(4) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 120.9(4) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C22 C17 C18 119.1(5) . . ? C22 C17 C22' 55.9(6) . . ? C18 C17 C22' 92.6(7) . . ? C22 C17 C18' 94.4(7) . . ? C18 C17 C18' 52.0(7) . . ? C22' C17 C18' 117.1(6) . . ? C22 C17 C9 119.6(4) . . ? C18 C17 C9 121.2(4) . . ? C22' C17 C9 123.5(5) . . ? C18' C17 C9 119.3(5) . . ? C17 C18 C19 120.2(6) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C20 C19 C18 121.6(6) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C22 C21 C20 120.1(6) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C17 C22 C21 120.4(6) . . ? C17 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C19 C20 C21' 93.1(8) . . ? C19 C20 C19' 50.0(7) . . ? C21' C20 C19' 120.8(6) . . ? C19 C20 C21 118.5(5) . . ? C21' C20 C21 58.3(7) . . ? C19' C20 C21 96.6(9) . . ? C19 C20 H20 120.7 . . ? C21' C20 H20 117.5 . . ? C19' C20 H20 121.2 . . ? C21 C20 H20 120.7 . . ? C19' C18' C17 121.2(9) . . ? C19' C18' H18' 119.4 . . ? C17 C18' H18' 119.4 . . ? C20 C19' C18' 119.3(9) . . ? C20 C19' H19' 120.4 . . ? C18' C19' H19' 120.4 . . ? C20 C21' C22' 118.4(8) . . ? C20 C21' H21' 120.8 . . ? C22' C21' H21' 120.8 . . ? C21' C22' C17 122.4(8) . . ? C21' C22' H22' 118.8 . . ? C17 C22' H22' 118.8 . . ? C8 N1 C9 105.0(3) . . ? C8 O2 C10 104.9(3) . . ? 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 -1.0(7) . . . . ? C7 C1 C2 C3 179.0(4) . . . . ? C1 C2 C3 C4 1.1(7) . . . . ? C2 C3 C4 C5 -0.1(7) . . . . ? C3 C4 C5 C6 -1.0(8) . . . . ? C4 C5 C6 C1 1.1(7) . . . . ? C2 C1 C6 C5 -0.1(7) . . . . ? C7 C1 C6 C5 179.9(4) . . . . ? C6 C1 C7 O1 176.0(5) . . . . ? C2 C1 C7 O1 -4.0(6) . . . . ? C6 C1 C7 C8 -3.5(7) . . . . ? C2 C1 C7 C8 176.5(4) . . . . ? O1 C7 C8 N1 174.0(4) . . . . ? C1 C7 C8 N1 -6.5(7) . . . . ? O1 C7 C8 O2 -3.6(6) . . . . ? C1 C7 C8 O2 175.9(4) . . . . ? N1 C9 C10 O2 0.0(4) . . . . ? C17 C9 C10 O2 -177.9(4) . . . . ? N1 C9 C10 C11 -178.4(4) . . . . ? C17 C9 C10 C11 3.7(8) . . . . ? C9 C10 C11 C16 5.1(7) . . . . ? O2 C10 C11 C16 -173.2(4) . . . . ? C9 C10 C11 C12 -175.2(5) . . . . ? O2 C10 C11 C12 6.4(5) . . . . ? C16 C11 C12 C13 1.2(6) . . . . ? C10 C11 C12 C13 -178.5(4) . . . . ? C11 C12 C13 C14 -0.7(7) . . . . ? C12 C13 C14 C15 -0.4(7) . . . . ? C13 C14 C15 C16 1.0(7) . . . . ? C14 C15 C16 C11 -0.5(7) . . . . ? C12 C11 C16 C15 -0.6(6) . . . . ? C10 C11 C16 C15 179.1(4) . . . . ? C10 C9 C17 C22 -132.2(7) . . . . ? N1 C9 C17 C22 50.1(7) . . . . ? C10 C9 C17 C18 52.0(8) . . . . ? N1 C9 C17 C18 -125.8(6) . . . . ? C10 C9 C17 C22' -65.6(9) . . . . ? N1 C9 C17 C22' 116.6(8) . . . . ? C10 C9 C17 C18' 113.0(9) . . . . ? N1 C9 C17 C18' -64.8(9) . . . . ? C22 C17 C18 C19 0.9(13) . . . . ? C22' C17 C18 C19 -50.9(11) . . . . ? C18' C17 C18 C19 72.0(10) . . . . ? C9 C17 C18 C19 176.8(8) . . . . ? C17 C18 C19 C20 1.9(16) . . . . ? C18 C17 C22 C21 -2.3(13) . . . . ? C22' C17 C22 C21 69.4(10) . . . . ? C18' C17 C22 C21 -50.7(12) . . . . ? C9 C17 C22 C21 -178.2(8) . . . . ? C20 C21 C22 C17 1.0(16) . . . . ? C18 C19 C20 C21' 52.1(12) . . . . ? C18 C19 C20 C19' -76.5(11) . . . . ? C18 C19 C20 C21 -3.2(15) . . . . ? C22 C21 C20 C19 1.8(15) . . . . ? C22 C21 C20 C21' -73.0(10) . . . . ? C22 C21 C20 C19' 49.3(13) . . . . ? C22 C17 C18' C19' 53.2(16) . . . . ? C18 C17 C18' C19' -70.8(15) . . . . ? C22' C17 C18' C19' 0(2) . . . . ? C9 C17 C18' C19' -179.1(13) . . . . ? C19 C20 C19' C18' 75.1(15) . . . . ? C21' C20 C19' C18' 10(2) . . . . ? C21 C20 C19' C18' -47.0(17) . . . . ? C17 C18' C19' C20 -4(2) . . . . ? C19 C20 C21' C22' -54.5(15) . . . . ? C19' C20 C21' C22' -10(2) . . . . ? C21 C20 C21' C22' 67.4(13) . . . . ? C20 C21' C22' C17 6(2) . . . . ? C22 C17 C22' C21' -76.1(13) . . . . ? C18 C17 C22' C21' 47.8(14) . . . . ? C18' C17 C22' C21' -0.2(18) . . . . ? C9 C17 C22' C21' 178.4(11) . . . . ? O2 C8 N1 C9 0.7(4) . . . . ? C7 C8 N1 C9 -177.0(4) . . . . ? C10 C9 N1 C8 -0.4(4) . . . . ? C17 C9 N1 C8 177.8(4) . . . . ? N1 C8 O2 C10 -0.7(4) . . . . ? C7 C8 O2 C10 177.3(3) . . . . ? C9 C10 O2 C8 0.4(4) . . . . ? C11 C10 O2 C8 179.2(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 C6 H6 N1 0.93 2.36 3.014(6) 127.6 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.207 _refine_diff_density_min -0.222 _refine_diff_density_rms 0.047 # Attachment 'web_deposit_cif_file_1_XueWeijian_1318329802.110716fm.cif' data_110716fm _database_code_depnum_ccdc_archive 'CCDC 848145' #TrackingRef 'web_deposit_cif_file_1_XueWeijian_1318329802.110716fm.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H17 N O2' _chemical_formula_weight 375.41 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 6.211(3) _cell_length_b 16.562(8) _cell_length_c 18.215(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.318(9) _cell_angle_gamma 90.00 _cell_volume 1868.5(15) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1782 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 21.10 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9866 _exptl_absorpt_correction_T_max 0.9916 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 17996 _diffrn_reflns_av_R_equivalents 0.0750 _diffrn_reflns_av_sigmaI/netI 0.0593 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3484 _reflns_number_gt 2592 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0313P)^2^+1.2154P] 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 3484 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1109 _refine_ls_R_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.1470 _refine_ls_wR_factor_gt 0.1372 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.151 _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 0.5978(5) 0.70877(18) 0.09565(16) 0.0340(7) Uani 1 1 d . . . C2 C 0.7224(5) 0.66997(19) 0.04440(16) 0.0395(8) Uani 1 1 d . . . H2 H 0.6832 0.6186 0.0278 0.047 Uiso 1 1 calc R . . C3 C 0.8979(5) 0.7060(2) 0.01887(17) 0.0426(8) Uani 1 1 d . . . H3 H 0.9782 0.6787 -0.0143 0.051 Uiso 1 1 calc R . . C4 C 0.9603(5) 0.78422(19) 0.04181(16) 0.0360(7) Uani 1 1 d . . . C5 C 0.8363(5) 0.82448(18) 0.09237(16) 0.0366(7) Uani 1 1 d . . . C6 C 0.6564(5) 0.78463(18) 0.11868(16) 0.0375(8) Uani 1 1 d . . . H6 H 0.5758 0.8107 0.1526 0.045 Uiso 1 1 calc R . . C7 C 0.8961(6) 0.9031(2) 0.1149(2) 0.0527(9) Uani 1 1 d . . . H7 H 0.8166 0.9298 0.1488 0.063 Uiso 1 1 calc R . . C8 C 1.0686(6) 0.9407(2) 0.0880(2) 0.0598(10) Uani 1 1 d . . . H8 H 1.1042 0.9932 0.1026 0.072 Uiso 1 1 calc R . . C9 C 1.1917(6) 0.9006(3) 0.0385(2) 0.0622(11) Uani 1 1 d . . . H9 H 1.3104 0.9262 0.0207 0.075 Uiso 1 1 calc R . . C10 C 1.1399(5) 0.8246(2) 0.01597(19) 0.0533(10) Uani 1 1 d . . . H10 H 1.2240 0.7986 -0.0170 0.064 Uiso 1 1 calc R . . C11 C 0.4097(5) 0.66400(19) 0.12072(17) 0.0365(7) Uani 1 1 d . . . C12 C 0.2836(5) 0.69528(18) 0.18040(16) 0.0347(7) Uani 1 1 d . . . C13 C 0.1414(5) 0.75950(17) 0.26490(16) 0.0318(7) Uani 1 1 d . . . C14 C 0.0271(5) 0.69039(18) 0.25340(15) 0.0323(7) Uani 1 1 d . . . C15 C 0.1092(5) 0.82912(17) 0.31351(16) 0.0324(7) Uani 1 1 d . . . C16 C -0.0927(5) 0.86641(19) 0.31422(17) 0.0400(8) Uani 1 1 d . . . H16 H -0.2098 0.8455 0.2855 0.048 Uiso 1 1 calc R . . C17 C -0.1197(6) 0.93332(19) 0.35668(18) 0.0456(9) Uani 1 1 d . . . H17 H -0.2547 0.9576 0.3565 0.055 Uiso 1 1 calc R . . C18 C 0.0511(6) 0.96477(19) 0.39953(18) 0.0457(9) Uani 1 1 d . . . H18 H 0.0321 1.0103 0.4282 0.055 Uiso 1 1 calc R . . C19 C 0.2507(6) 0.9286(2) 0.39991(19) 0.0487(9) Uani 1 1 d . . . H19 H 0.3665 0.9495 0.4292 0.058 Uiso 1 1 calc R . . C20 C 0.2797(5) 0.86106(19) 0.35682(18) 0.0426(8) Uani 1 1 d . . . H20 H 0.4152 0.8371 0.3571 0.051 Uiso 1 1 calc R . . C21 C -0.1547(5) 0.65213(18) 0.28663(16) 0.0335(7) Uani 1 1 d . . . C22 C -0.2231(5) 0.6793(2) 0.35267(17) 0.0434(8) Uani 1 1 d . . . H22 H -0.1494 0.7213 0.3773 0.052 Uiso 1 1 calc R . . C23 C -0.3975(5) 0.6453(2) 0.38258(19) 0.0512(9) Uani 1 1 d . . . H23 H -0.4405 0.6645 0.4272 0.061 Uiso 1 1 calc R . . C24 C -0.5083(6) 0.5839(2) 0.3477(2) 0.0554(10) Uani 1 1 d . . . H24 H -0.6290 0.5620 0.3676 0.066 Uiso 1 1 calc R . . C25 C -0.4404(6) 0.5542(2) 0.2825(2) 0.0568(10) Uani 1 1 d . . . H25 H -0.5139 0.5114 0.2590 0.068 Uiso 1 1 calc R . . C26 C -0.2644(5) 0.5876(2) 0.25201(18) 0.0449(8) Uani 1 1 d . . . H26 H -0.2189 0.5670 0.2083 0.054 Uiso 1 1 calc R . . N1 N 0.3064(4) 0.76080(14) 0.21858(13) 0.0347(6) Uani 1 1 d . . . O1 O 0.3553(4) 0.59961(14) 0.09225(13) 0.0517(6) Uani 1 1 d . . . O2 O 0.1164(3) 0.64853(12) 0.19836(11) 0.0361(5) 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 0.0348(18) 0.0354(17) 0.0324(16) -0.0013(13) 0.0054(14) 0.0040(14) C2 0.0436(19) 0.0393(18) 0.0366(18) -0.0041(14) 0.0096(15) 0.0024(15) C3 0.0401(19) 0.051(2) 0.0382(18) -0.0037(16) 0.0153(15) 0.0110(16) C4 0.0332(18) 0.0447(19) 0.0306(16) 0.0042(14) 0.0057(14) 0.0018(15) C5 0.0388(18) 0.0370(17) 0.0342(17) 0.0064(14) 0.0045(14) 0.0029(15) C6 0.0398(18) 0.0401(18) 0.0341(17) -0.0025(14) 0.0127(15) 0.0032(15) C7 0.055(2) 0.048(2) 0.058(2) -0.0039(18) 0.0150(19) -0.0053(18) C8 0.066(3) 0.049(2) 0.065(3) 0.0005(19) 0.009(2) -0.020(2) C9 0.047(2) 0.075(3) 0.066(3) 0.008(2) 0.010(2) -0.021(2) C10 0.040(2) 0.071(3) 0.050(2) 0.0050(19) 0.0141(17) -0.0033(19) C11 0.0370(18) 0.0356(18) 0.0374(17) -0.0009(14) 0.0058(14) 0.0005(14) C12 0.0316(17) 0.0366(17) 0.0371(17) -0.0014(14) 0.0103(14) -0.0004(14) C13 0.0289(16) 0.0341(16) 0.0331(16) -0.0022(13) 0.0063(13) 0.0050(13) C14 0.0307(17) 0.0383(17) 0.0283(16) -0.0021(13) 0.0057(13) 0.0055(14) C15 0.0306(17) 0.0353(17) 0.0324(16) 0.0008(13) 0.0096(13) -0.0025(14) C16 0.0369(19) 0.0443(19) 0.0392(18) -0.0007(15) 0.0046(15) 0.0015(15) C17 0.052(2) 0.0395(19) 0.047(2) 0.0007(16) 0.0139(17) 0.0110(17) C18 0.069(3) 0.0297(17) 0.0406(19) -0.0026(14) 0.0177(18) -0.0013(17) C19 0.051(2) 0.044(2) 0.052(2) -0.0112(17) 0.0069(17) -0.0097(18) C20 0.0364(19) 0.0436(19) 0.049(2) -0.0052(16) 0.0094(16) -0.0006(15) C21 0.0299(16) 0.0367(17) 0.0337(17) 0.0014(14) 0.0009(13) 0.0036(14) C22 0.045(2) 0.0436(19) 0.0432(19) -0.0046(15) 0.0145(16) -0.0075(16) C23 0.051(2) 0.054(2) 0.051(2) -0.0031(18) 0.0230(18) -0.0037(18) C24 0.041(2) 0.067(3) 0.060(2) 0.005(2) 0.0168(18) -0.0123(19) C25 0.051(2) 0.062(2) 0.057(2) -0.0002(19) 0.0014(19) -0.0252(19) C26 0.047(2) 0.050(2) 0.0384(19) -0.0034(16) 0.0074(16) -0.0058(17) N1 0.0339(14) 0.0357(14) 0.0360(14) -0.0013(12) 0.0127(12) 0.0000(12) O1 0.0562(15) 0.0450(14) 0.0562(15) -0.0131(12) 0.0201(12) -0.0133(12) O2 0.0353(12) 0.0378(12) 0.0365(12) -0.0055(9) 0.0104(10) -0.0035(10) _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 C6 1.365(4) . ? C1 C2 1.411(4) . ? C1 C11 1.485(4) . ? C2 C3 1.356(4) . ? C2 H2 0.9300 . ? C3 C4 1.406(4) . ? C3 H3 0.9300 . ? C4 C5 1.411(4) . ? C4 C10 1.412(4) . ? C5 C7 1.407(4) . ? C5 C6 1.412(4) . ? C6 H6 0.9300 . ? C7 C8 1.363(5) . ? C7 H7 0.9300 . ? C8 C9 1.394(5) . ? C8 H8 0.9300 . ? C9 C10 1.355(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 O1 1.222(3) . ? C11 C12 1.480(4) . ? C12 N1 1.291(4) . ? C12 O2 1.355(3) . ? C13 C14 1.355(4) . ? C13 N1 1.376(4) . ? C13 C15 1.477(4) . ? C14 O2 1.370(3) . ? C14 C21 1.465(4) . ? C15 C20 1.377(4) . ? C15 C16 1.399(4) . ? C16 C17 1.369(4) . ? C16 H16 0.9300 . ? C17 C18 1.371(5) . ? C17 H17 0.9300 . ? C18 C19 1.377(5) . ? C18 H18 0.9300 . ? C19 C20 1.386(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.381(4) . ? C21 C26 1.392(4) . ? C22 C23 1.370(4) . ? C22 H22 0.9300 . ? C23 C24 1.359(5) . ? C23 H23 0.9300 . ? C24 C25 1.379(5) . ? C24 H24 0.9300 . ? C25 C26 1.379(5) . ? C25 H25 0.9300 . ? C26 H26 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 C6 C1 C2 118.4(3) . . ? C6 C1 C11 124.3(3) . . ? C2 C1 C11 117.4(3) . . ? C3 C2 C1 121.4(3) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 121.0(3) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 118.5(3) . . ? C3 C4 C10 123.0(3) . . ? C5 C4 C10 118.5(3) . . ? C7 C5 C4 118.9(3) . . ? C7 C5 C6 122.1(3) . . ? C4 C5 C6 119.0(3) . . ? C1 C6 C5 121.7(3) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? C8 C7 C5 121.0(3) . . ? C8 C7 H7 119.5 . . ? C5 C7 H7 119.5 . . ? C7 C8 C9 120.0(4) . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.6(3) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C4 121.0(3) . . ? C9 C10 H10 119.5 . . ? C4 C10 H10 119.5 . . ? O1 C11 C12 118.2(3) . . ? O1 C11 C1 120.3(3) . . ? C12 C11 C1 121.5(3) . . ? N1 C12 O2 113.9(3) . . ? N1 C12 C11 130.3(3) . . ? O2 C12 C11 115.8(3) . . ? C14 C13 N1 108.9(2) . . ? C14 C13 C15 131.3(3) . . ? N1 C13 C15 119.8(3) . . ? C13 C14 O2 107.7(2) . . ? C13 C14 C21 135.5(3) . . ? O2 C14 C21 116.8(3) . . ? C20 C15 C16 118.4(3) . . ? C20 C15 C13 120.7(3) . . ? C16 C15 C13 120.8(3) . . ? C17 C16 C15 120.7(3) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 120.4(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C19 119.7(3) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C18 C19 C20 120.3(3) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C15 C20 C19 120.5(3) . . ? C15 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C22 C21 C26 118.2(3) . . ? C22 C21 C14 121.1(3) . . ? C26 C21 C14 120.7(3) . . ? C23 C22 C21 121.2(3) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C24 C23 C22 120.6(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 119.5(3) . . ? C23 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? C26 C25 C24 120.5(3) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C21 120.1(3) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? C12 N1 C13 105.1(2) . . ? C12 O2 C14 104.3(2) . . ? 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 0.8(5) . . . . ? C11 C1 C2 C3 -179.5(3) . . . . ? C1 C2 C3 C4 -1.0(5) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C2 C3 C4 C10 -179.1(3) . . . . ? C3 C4 C5 C7 -179.2(3) . . . . ? C10 C4 C5 C7 0.1(4) . . . . ? C3 C4 C5 C6 0.8(4) . . . . ? C10 C4 C5 C6 -179.9(3) . . . . ? C2 C1 C6 C5 0.2(5) . . . . ? C11 C1 C6 C5 -179.5(3) . . . . ? C7 C5 C6 C1 179.0(3) . . . . ? C4 C5 C6 C1 -1.0(5) . . . . ? C4 C5 C7 C8 0.9(5) . . . . ? C6 C5 C7 C8 -179.1(3) . . . . ? C5 C7 C8 C9 -1.4(6) . . . . ? C7 C8 C9 C10 0.9(6) . . . . ? C8 C9 C10 C4 0.2(6) . . . . ? C3 C4 C10 C9 178.7(3) . . . . ? C5 C4 C10 C9 -0.7(5) . . . . ? C6 C1 C11 O1 172.9(3) . . . . ? C2 C1 C11 O1 -6.8(4) . . . . ? C6 C1 C11 C12 -7.3(5) . . . . ? C2 C1 C11 C12 173.0(3) . . . . ? O1 C11 C12 N1 -179.6(3) . . . . ? C1 C11 C12 N1 0.6(5) . . . . ? O1 C11 C12 O2 0.1(4) . . . . ? C1 C11 C12 O2 -179.7(3) . . . . ? N1 C13 C14 O2 -1.4(3) . . . . ? C15 C13 C14 O2 175.4(3) . . . . ? N1 C13 C14 C21 176.2(3) . . . . ? C15 C13 C14 C21 -6.9(6) . . . . ? C14 C13 C15 C20 133.8(3) . . . . ? N1 C13 C15 C20 -49.6(4) . . . . ? C14 C13 C15 C16 -49.1(5) . . . . ? N1 C13 C15 C16 127.5(3) . . . . ? C20 C15 C16 C17 0.4(4) . . . . ? C13 C15 C16 C17 -176.8(3) . . . . ? C15 C16 C17 C18 -0.3(5) . . . . ? C16 C17 C18 C19 -0.2(5) . . . . ? C17 C18 C19 C20 0.5(5) . . . . ? C16 C15 C20 C19 0.0(5) . . . . ? C13 C15 C20 C19 177.2(3) . . . . ? C18 C19 C20 C15 -0.4(5) . . . . ? C13 C14 C21 C22 -12.7(5) . . . . ? O2 C14 C21 C22 164.8(3) . . . . ? C13 C14 C21 C26 166.8(3) . . . . ? O2 C14 C21 C26 -15.7(4) . . . . ? C26 C21 C22 C23 -1.7(5) . . . . ? C14 C21 C22 C23 177.8(3) . . . . ? C21 C22 C23 C24 -0.2(5) . . . . ? C22 C23 C24 C25 1.7(6) . . . . ? C23 C24 C25 C26 -1.4(6) . . . . ? C24 C25 C26 C21 -0.5(5) . . . . ? C22 C21 C26 C25 2.0(5) . . . . ? C14 C21 C26 C25 -177.5(3) . . . . ? O2 C12 N1 C13 -1.1(3) . . . . ? C11 C12 N1 C13 178.7(3) . . . . ? C14 C13 N1 C12 1.5(3) . . . . ? C15 C13 N1 C12 -175.8(3) . . . . ? N1 C12 O2 C14 0.2(3) . . . . ? C11 C12 O2 C14 -179.6(2) . . . . ? C13 C14 O2 C12 0.8(3) . . . . ? C21 C14 O2 C12 -177.4(2) . . . . ? 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 C2 H2 O1 0.93 2.45 2.760(4) 99.7 . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.176 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.045 # Attachment 'web_deposit_cif_file_2_XueWeijian_1318329802.110717am.cif' data_110717am _database_code_depnum_ccdc_archive 'CCDC 848146' #TrackingRef 'web_deposit_cif_file_2_XueWeijian_1318329802.110717am.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 0.0016 '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 Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.5338(9) _cell_length_b 21.451(3) _cell_length_c 12.1305(16) _cell_angle_alpha 90.00 _cell_angle_beta 95.016(3) _cell_angle_gamma 90.00 _cell_volume 1693.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1502 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 25.79 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9854 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 9012 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0839 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7433 _reflns_number_gt 4743 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0237P)^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 SHELXL _refine_ls_extinction_coef 0.0054(3) _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 -1(2) _refine_ls_number_reflns 7433 _refine_ls_number_parameters 910 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1036 _refine_ls_R_factor_gt 0.0606 _refine_ls_wR_factor_ref 0.1213 _refine_ls_wR_factor_gt 0.1052 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0.265 _refine_ls_shift/su_mean 0.062 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 C41 C 0.6213(12) 0.7961(4) 0.3857(6) 0.040(2) Uani 1 1 d . . . H41 H 0.6007 0.8383 0.3709 0.047 Uiso 1 1 calc R . . C1A C -0.4895(15) 0.1679(4) -0.2419(8) 0.064(3) Uani 1 1 d . . . H1A1 H -0.5858 0.1822 -0.1920 0.095 Uiso 1 1 calc R . . H1A2 H -0.5508 0.1351 -0.2874 0.095 Uiso 1 1 calc R . . H1A3 H -0.4531 0.2019 -0.2879 0.095 Uiso 1 1 calc R . . C2A C -0.2950(13) 0.1432(4) -0.1749(8) 0.052(2) Uani 1 1 d . . . H2A1 H -0.3324 0.1155 -0.1167 0.062 Uiso 1 1 calc R . . H2A2 H -0.2105 0.1202 -0.2228 0.062 Uiso 1 1 calc R . . C3A C 0.0008(14) 0.1833(4) -0.0708(8) 0.054(2) Uani 1 1 d . . . C4A C 0.0830(12) 0.1253(4) -0.0544(7) 0.053(2) Uani 1 1 d . . . H4A H 0.0139 0.0899 -0.0819 0.064 Uiso 1 1 calc R . . C5A C 0.2762(15) 0.1213(4) 0.0056(8) 0.060(3) Uani 1 1 d . . . H5A H 0.3336 0.0820 0.0187 0.072 Uiso 1 1 calc R . . C6A C 0.3826(13) 0.1715(4) 0.0452(7) 0.038(2) Uani 1 1 d . . . C7A C 0.2907(15) 0.2307(4) 0.0300(6) 0.053(2) Uani 1 1 d . . . H7A H 0.3556 0.2658 0.0617 0.063 Uiso 1 1 calc R . . C8A C 0.1030(13) 0.2366(4) -0.0325(6) 0.044(2) Uani 1 1 d . . . H8A H 0.0469 0.2758 -0.0483 0.053 Uiso 1 1 calc R . . C9A C 0.5864(14) 0.1610(4) 0.1079(7) 0.047(2) Uani 1 1 d . . . C10A C 0.7157(12) 0.2119(4) 0.1571(6) 0.0321(18) Uani 1 1 d . . . C11A C 0.9780(12) 0.2488(3) 0.2574(6) 0.0326(18) Uani 1 1 d . . . C12A C 0.8483(14) 0.2957(4) 0.2246(7) 0.057(2) Uani 1 1 d . . . H12A H 0.8695 0.3377 0.2408 0.069 Uiso 1 1 calc R . . C13A C 1.1818(13) 0.2423(4) 0.3202(5) 0.039(2) Uani 1 1 d . . . C14A C 1.2887(12) 0.1855(3) 0.3292(7) 0.0346(18) Uani 1 1 d . . . H14A H 1.2328 0.1501 0.2939 0.041 Uiso 1 1 calc R . . C15A C 1.4734(13) 0.1822(4) 0.3892(7) 0.052(2) Uani 1 1 d . . . H15A H 1.5422 0.1442 0.3921 0.062 Uiso 1 1 calc R . . C16A C 1.5636(13) 0.2311(3) 0.4453(6) 0.0335(18) Uani 1 1 d . . . C17A C 1.4559(14) 0.2879(4) 0.4384(7) 0.049(2) Uani 1 1 d . . . H17A H 1.5089 0.3228 0.4762 0.059 Uiso 1 1 calc R . . C18A C 1.2682(14) 0.2911(4) 0.3740(7) 0.053(2) Uani 1 1 d . . . H18A H 1.2001 0.3292 0.3684 0.064 Uiso 1 1 calc R . . C19A C 1.8544(14) 0.1746(4) 0.5199(7) 0.045(2) Uani 1 1 d . . . H19A H 1.8956 0.1612 0.4488 0.054 Uiso 1 1 calc R . . H19B H 1.7706 0.1422 0.5490 0.054 Uiso 1 1 calc R . . C20A C 2.0445(14) 0.1877(5) 0.6006(9) 0.068(3) Uani 1 1 d . . . H20A H 2.1262 0.2196 0.5706 0.102 Uiso 1 1 calc R . . H20B H 2.1245 0.1502 0.6112 0.102 Uiso 1 1 calc R . . H20C H 2.0015 0.2012 0.6703 0.102 Uiso 1 1 calc R . . C1B C -0.5611(14) 0.4632(4) 0.5142(7) 0.051(2) Uani 1 1 d . . . H1B1 H -0.5245 0.4443 0.4469 0.076 Uiso 1 1 calc R . . H1B2 H -0.6237 0.5030 0.4979 0.076 Uiso 1 1 calc R . . H1B3 H -0.6562 0.4367 0.5481 0.076 Uiso 1 1 calc R . . C2B C -0.3748(14) 0.4716(4) 0.5905(8) 0.059(3) Uani 1 1 d . . . H2B1 H -0.2866 0.5030 0.5618 0.070 Uiso 1 1 calc R . . H2B2 H -0.4120 0.4853 0.6623 0.070 Uiso 1 1 calc R . . C3B C -0.0815(13) 0.4107(4) 0.6639(7) 0.050(2) Uani 1 1 d . . . C4B C 0.0158(15) 0.3543(4) 0.6709(8) 0.059(3) Uani 1 1 d . . . H4B H -0.0465 0.3201 0.6349 0.070 Uiso 1 1 calc R . . C5B C 0.2015(14) 0.3472(4) 0.7292(7) 0.053(2) Uani 1 1 d . . . H5B H 0.2674 0.3087 0.7317 0.063 Uiso 1 1 calc R . . C6B C 0.2960(12) 0.4005(4) 0.7875(8) 0.049(2) Uani 1 1 d . . . C7B C 0.1952(15) 0.4549(5) 0.7821(8) 0.055(2) Uani 1 1 d . . . H7B H 0.2533 0.4885 0.8218 0.067 Uiso 1 1 calc R . . C8B C 0.0024(14) 0.4640(4) 0.7183(6) 0.042(2) Uani 1 1 d . . . H8B H -0.0628 0.5025 0.7132 0.050 Uiso 1 1 calc R . . C9B C 0.4871(14) 0.3954(4) 0.8533(7) 0.049(2) Uani 1 1 d . . . C10B C 0.6196(13) 0.3499(3) 0.8836(8) 0.048(2) Uani 1 1 d . . . H10B H 0.5988 0.3082 0.8644 0.058 Uiso 1 1 calc R . . C11B C 0.7628(13) 0.4309(4) 0.9469(7) 0.045(2) Uani 1 1 d . . . C12B C 0.8861(14) 0.4828(3) 1.0012(7) 0.042(2) Uani 1 1 d . . . C13B C 1.0875(13) 0.4698(4) 1.0598(6) 0.038(2) Uani 1 1 d . . . C14B C 1.1747(11) 0.4130(3) 1.0840(7) 0.044(2) Uani 1 1 d . . . H14B H 1.1020 0.3771 1.0623 0.052 Uiso 1 1 calc R . . C15B C 1.3646(14) 0.4072(4) 1.1389(7) 0.053(2) Uani 1 1 d . . . H15B H 1.4230 0.3678 1.1482 0.064 Uiso 1 1 calc R . . C16B C 1.4736(13) 0.4591(3) 1.1813(6) 0.0312(18) Uani 1 1 d . . . C17B C 1.3816(14) 0.5174(4) 1.1600(7) 0.050(2) Uani 1 1 d . . . H17B H 1.4505 0.5531 1.1864 0.060 Uiso 1 1 calc R . . C18B C 1.1972(13) 0.5237(4) 1.1025(7) 0.042(2) Uani 1 1 d . . . H18B H 1.1406 0.5631 1.0905 0.051 Uiso 1 1 calc R . . C19B C 1.7655(15) 0.5019(4) 1.2909(8) 0.054(3) Uani 1 1 d . . . H19C H 1.6788 0.5229 1.3402 0.065 Uiso 1 1 calc R . . H19D H 1.8040 0.5314 1.2358 0.065 Uiso 1 1 calc R . . C20B C 1.9526(14) 0.4757(5) 1.3546(7) 0.069(3) Uani 1 1 d . . . H20D H 1.9128 0.4535 1.4180 0.104 Uiso 1 1 calc R . . H20E H 2.0438 0.5091 1.3785 0.104 Uiso 1 1 calc R . . H20F H 2.0212 0.4478 1.3082 0.104 Uiso 1 1 calc R . . C1C C -0.5717(14) 0.6832(5) 0.0107(7) 0.054(3) Uani 1 1 d . . . H1C1 H -0.6602 0.7140 0.0388 0.082 Uiso 1 1 calc R . . H1C2 H -0.6438 0.6443 0.0019 0.082 Uiso 1 1 calc R . . H1C3 H -0.5309 0.6966 -0.0597 0.082 Uiso 1 1 calc R . . C2C C -0.3811(14) 0.6749(4) 0.0918(8) 0.058(3) Uani 1 1 d . . . H2C1 H -0.4218 0.6632 0.1640 0.070 Uiso 1 1 calc R . . H2C2 H -0.2954 0.6419 0.0662 0.070 Uiso 1 1 calc R . . C3C C -0.0825(13) 0.7312(4) 0.1664(7) 0.046(2) Uani 1 1 d . . . C4C C 0.0016(14) 0.6812(3) 0.2216(6) 0.037(2) Uani 1 1 d . . . H4C H -0.0691 0.6435 0.2200 0.044 Uiso 1 1 calc R . . C5C C 0.1920(15) 0.6859(4) 0.2805(7) 0.055(2) Uani 1 1 d . . . H5C H 0.2542 0.6510 0.3141 0.067 Uiso 1 1 calc R . . C6C C 0.2899(13) 0.7440(3) 0.2887(6) 0.0335(18) Uani 1 1 d . . . C7C C 0.2017(13) 0.7960(4) 0.2323(7) 0.044(2) Uani 1 1 d . . . H7C H 0.2671 0.8346 0.2360 0.053 Uiso 1 1 calc R . . C8C C 0.0142(14) 0.7882(4) 0.1709(7) 0.045(2) Uani 1 1 d . . . H8C H -0.0468 0.8218 0.1324 0.054 Uiso 1 1 calc R . . C9C C 0.4891(13) 0.7490(4) 0.3523(6) 0.039(2) Uani 1 1 d . . . C10C C 0.7458(15) 0.7115(4) 0.4442(7) 0.053(2) Uani 1 1 d . . . C11C C 0.8885(12) 0.6599(4) 0.5004(6) 0.0373(19) Uani 1 1 d . . . C12C C 1.0897(11) 0.6731(3) 0.5605(6) 0.0348(18) Uani 1 1 d . . . C13C C 1.1990(12) 0.6225(3) 0.6051(7) 0.041(2) Uani 1 1 d . . . H13C H 1.1379 0.5835 0.5961 0.049 Uiso 1 1 calc R . . C14C C 1.3819(14) 0.6250(4) 0.6592(8) 0.051(2) Uani 1 1 d . . . H14C H 1.4510 0.5888 0.6823 0.062 Uiso 1 1 calc R . . C15C C 1.4735(11) 0.6860(3) 0.6820(6) 0.0309(17) Uani 1 1 d . . . C16C C 1.3681(13) 0.7364(4) 0.6416(7) 0.048(2) Uani 1 1 d . . . H16C H 1.4240 0.7759 0.6545 0.057 Uiso 1 1 calc R . . C17C C 1.1811(13) 0.7308(4) 0.5822(7) 0.047(2) Uani 1 1 d . . . H17C H 1.1134 0.7666 0.5556 0.057 Uiso 1 1 calc R . . C18C C 1.7696(13) 0.6446(4) 0.7859(7) 0.043(2) Uani 1 1 d . . . H18C H 1.8091 0.6168 0.7283 0.052 Uiso 1 1 calc R . . H18D H 1.6844 0.6215 0.8332 0.052 Uiso 1 1 calc R . . C19C C 1.9581(15) 0.6689(5) 0.8526(8) 0.077(3) Uani 1 1 d . . . H19E H 2.0304 0.6969 0.8080 0.116 Uiso 1 1 calc R . . H19F H 2.0461 0.6346 0.8758 0.116 Uiso 1 1 calc R . . H19G H 1.9180 0.6906 0.9165 0.116 Uiso 1 1 calc R . . C1D C -0.4819(14) 0.9773(5) 0.2559(8) 0.056(2) Uani 1 1 d . . . H1D1 H -0.4439 0.9441 0.2089 0.084 Uiso 1 1 calc R . . H1D2 H -0.5505 1.0094 0.2117 0.084 Uiso 1 1 calc R . . H1D3 H -0.5725 0.9616 0.3076 0.084 Uiso 1 1 calc R . . C2D C -0.2926(14) 1.0037(5) 0.3179(9) 0.066(3) Uani 1 1 d . . . H2D1 H -0.2066 1.0242 0.2676 0.080 Uiso 1 1 calc R . . H2D2 H -0.3289 1.0336 0.3729 0.080 Uiso 1 1 calc R . . C3D C -0.0008(14) 0.9613(4) 0.4280(7) 0.054(2) Uani 1 1 d . . . C4D C 0.1052(14) 0.9067(4) 0.4693(7) 0.046(2) Uani 1 1 d . . . H4D H 0.0459 0.8676 0.4575 0.055 Uiso 1 1 calc R . . C5D C 0.2986(14) 0.9124(4) 0.5277(7) 0.046(2) Uani 1 1 d . . . H5D H 0.3688 0.8771 0.5547 0.055 Uiso 1 1 calc R . . C6D C 0.3861(14) 0.9719(4) 0.5453(7) 0.046(2) Uani 1 1 d . . . C7D C 0.2768(15) 1.0244(4) 0.5076(8) 0.055(2) Uani 1 1 d . . . H7D H 0.3296 1.0641 0.5223 0.066 Uiso 1 1 calc R . . C8D C 0.0796(13) 1.0165(4) 0.4452(7) 0.051(2) Uani 1 1 d . . . H8D H 0.0088 1.0514 0.4167 0.061 Uiso 1 1 calc R . . C9D C 0.5907(15) 0.9813(4) 0.6083(7) 0.053(2) Uani 1 1 d . . . C10D C 0.7060(11) 0.9325(3) 0.6557(6) 0.0307(17) Uani 1 1 d . . . C11D C 0.8529(15) 0.8503(5) 0.7267(9) 0.069(3) Uani 1 1 d . . . H11D H 0.8769 0.8089 0.7468 0.083 Uiso 1 1 calc R . . C12D C 0.9782(13) 0.8974(4) 0.7558(7) 0.043(2) Uani 1 1 d . . . C13D C 1.1769(14) 0.9022(4) 0.8216(7) 0.047(2) Uani 1 1 d . . . C14D C 1.2664(16) 0.8529(4) 0.8762(8) 0.063(3) Uani 1 1 d . . . H14D H 1.1964 0.8151 0.8717 0.075 Uiso 1 1 calc R . . C15D C 1.4546(16) 0.8546(4) 0.9383(9) 0.067(3) Uani 1 1 d . . . H15D H 1.5084 0.8188 0.9732 0.080 Uiso 1 1 calc R . . C16D C 1.5631(12) 0.9114(4) 0.9476(7) 0.0367(19) Uani 1 1 d . . . C17D C 1.4728(15) 0.9633(5) 0.8915(7) 0.057(3) Uani 1 1 d . . . H17D H 1.5379 1.0019 0.8969 0.068 Uiso 1 1 calc R . . C18D C 1.2873(11) 0.9570(4) 0.8283(6) 0.0342(18) Uani 1 1 d . . . H18E H 1.2347 0.9913 0.7884 0.041 Uiso 1 1 calc R . . C19D C 1.8490(13) 0.9720(4) 1.0220(7) 0.041(2) Uani 1 1 d . . . H19H H 1.8846 0.9881 0.9514 0.049 Uiso 1 1 calc R . . H19I H 1.7629 1.0023 1.0552 0.049 Uiso 1 1 calc R . . C20D C 2.0359(15) 0.9592(5) 1.0958(8) 0.061(3) Uani 1 1 d . . . H20G H 1.9983 0.9403 1.1628 0.092 Uiso 1 1 calc R . . H20H H 2.1072 0.9976 1.1130 0.092 Uiso 1 1 calc R . . H20I H 2.1237 0.9315 1.0595 0.092 Uiso 1 1 calc R . . N1A N 0.6851(11) 0.2720(3) 0.1650(6) 0.0436(17) Uani 1 1 d . . . N1B N 0.7965(12) 0.3724(3) 0.9487(6) 0.053(2) Uani 1 1 d . . . N1C N 0.5794(9) 0.6948(2) 0.3929(4) 0.0245(13) Uani 1 1 d . . . N1D N 0.6809(10) 0.8716(3) 0.6621(6) 0.0374(15) Uani 1 1 d . . . O1A O -0.1863(9) 0.1953(2) -0.1288(5) 0.0498(16) Uani 1 1 d . . . O2A O 0.6591(10) 0.1082(3) 0.1172(6) 0.0623(18) Uani 1 1 d . . . O3A O 0.8979(9) 0.1957(2) 0.2156(5) 0.0425(14) Uani 1 1 d . . . O4A O 1.7441(9) 0.2309(3) 0.5087(5) 0.0499(16) Uani 1 1 d . . . O1B O -0.2676(9) 0.4120(3) 0.6008(5) 0.0547(17) Uani 1 1 d . . . O2B O 0.5825(9) 0.4507(3) 0.8948(5) 0.0453(15) Uani 1 1 d . . . O3B O 0.8187(11) 0.5358(3) 0.9891(6) 0.071(2) Uani 1 1 d . . . O4B O 1.6587(10) 0.4489(3) 1.2383(5) 0.0591(18) Uani 1 1 d . . . O1C O -0.2707(9) 0.7308(3) 0.0997(5) 0.0495(16) Uani 1 1 d . . . O2C O 0.7904(12) 0.7704(4) 0.4452(7) 0.093(2) Uani 1 1 d . . . O3C O 0.8190(10) 0.6084(3) 0.4909(6) 0.0672(19) Uani 1 1 d . . . O4C O 1.6613(9) 0.6952(3) 0.7390(5) 0.0618(18) Uani 1 1 d . . . O1D O -0.1839(9) 0.9491(2) 0.3720(5) 0.0447(15) Uani 1 1 d . . . O2D O 0.6592(11) 1.0358(3) 0.6184(6) 0.067(2) Uani 1 1 d . . . O3D O 0.8972(8) 0.9507(2) 0.7148(4) 0.0398(13) Uani 1 1 d . . . O4D O 1.7414(9) 0.9114(3) 1.0071(5) 0.0538(16) 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 C41 0.040(5) 0.031(4) 0.044(5) 0.008(3) -0.016(4) -0.009(4) C1A 0.048(6) 0.064(6) 0.075(6) 0.018(5) -0.018(5) -0.007(5) C2A 0.032(5) 0.063(5) 0.061(6) -0.006(4) 0.000(4) 0.021(4) C3A 0.029(5) 0.066(6) 0.066(6) -0.011(5) -0.010(4) 0.002(4) C4A 0.025(5) 0.046(5) 0.085(6) 0.019(4) -0.020(4) -0.005(4) C5A 0.061(6) 0.028(4) 0.089(7) 0.009(4) -0.002(5) 0.018(4) C6A 0.036(5) 0.036(4) 0.044(5) -0.003(4) 0.004(4) 0.011(4) C7A 0.082(7) 0.050(5) 0.026(4) -0.006(4) 0.005(4) 0.018(5) C8A 0.052(6) 0.047(5) 0.028(4) 0.011(4) -0.019(4) 0.017(4) C9A 0.042(5) 0.058(5) 0.041(5) 0.004(4) 0.008(4) 0.017(4) C10A 0.033(5) 0.036(4) 0.028(4) 0.007(3) 0.007(3) 0.006(3) C11A 0.039(5) 0.027(4) 0.031(4) 0.010(3) -0.004(3) -0.007(3) C12A 0.049(6) 0.053(5) 0.064(6) -0.002(4) -0.029(4) 0.012(4) C13A 0.048(5) 0.053(5) 0.016(3) -0.014(3) -0.003(3) 0.005(4) C14A 0.039(5) 0.019(3) 0.046(5) 0.002(3) 0.005(4) 0.004(3) C15A 0.038(5) 0.037(4) 0.080(6) -0.016(4) -0.002(5) 0.016(4) C16A 0.044(5) 0.027(4) 0.030(4) 0.001(3) 0.011(4) 0.015(3) C17A 0.056(6) 0.022(4) 0.063(6) -0.010(4) -0.023(4) 0.001(4) C18A 0.053(6) 0.038(4) 0.066(6) 0.012(4) -0.015(5) 0.016(4) C19A 0.058(6) 0.048(5) 0.029(4) 0.007(4) 0.006(4) -0.001(4) C20A 0.037(5) 0.072(6) 0.089(7) 0.007(5) -0.025(5) 0.010(4) C1B 0.065(6) 0.041(4) 0.046(5) -0.007(4) 0.001(4) 0.006(4) C2B 0.031(5) 0.046(5) 0.096(7) -0.007(5) -0.013(5) 0.013(4) C3B 0.033(5) 0.049(5) 0.064(6) 0.002(4) -0.016(4) -0.019(4) C4B 0.039(5) 0.052(6) 0.083(7) -0.003(5) -0.003(5) 0.003(4) C5B 0.054(6) 0.036(4) 0.065(6) -0.012(4) -0.010(4) -0.004(4) C6B 0.019(4) 0.033(4) 0.094(6) 0.020(4) -0.001(4) 0.000(4) C7B 0.044(6) 0.070(6) 0.051(5) -0.016(5) -0.002(4) -0.003(5) C8B 0.052(5) 0.044(4) 0.029(4) 0.014(3) 0.002(4) -0.003(4) C9B 0.037(5) 0.054(5) 0.058(6) -0.025(4) 0.015(4) -0.001(4) C10B 0.043(5) 0.020(4) 0.082(6) -0.007(4) 0.007(4) -0.003(3) C11B 0.033(5) 0.051(5) 0.049(5) 0.005(4) -0.011(4) 0.004(4) C12B 0.054(6) 0.019(4) 0.052(5) -0.002(3) -0.002(4) -0.014(4) C13B 0.041(5) 0.039(4) 0.032(4) 0.003(3) 0.000(4) -0.009(4) C14B 0.023(4) 0.031(4) 0.074(6) -0.002(4) -0.012(4) -0.018(3) C15B 0.050(6) 0.031(4) 0.078(6) -0.016(4) 0.005(5) -0.012(4) C16B 0.051(5) 0.020(3) 0.024(4) 0.005(3) 0.008(3) -0.008(3) C17B 0.067(6) 0.032(4) 0.052(5) -0.023(4) 0.012(4) -0.016(4) C18B 0.035(5) 0.042(5) 0.048(5) -0.001(4) -0.006(4) -0.016(4) C19B 0.070(6) 0.048(5) 0.043(5) -0.017(4) -0.008(4) -0.030(4) C20B 0.041(6) 0.118(8) 0.048(5) -0.046(5) 0.002(4) 0.011(5) C1C 0.047(6) 0.070(6) 0.046(5) -0.003(5) 0.001(4) -0.015(5) C2C 0.056(6) 0.039(5) 0.074(6) 0.000(4) -0.024(5) -0.005(4) C3C 0.039(5) 0.054(5) 0.040(5) -0.001(4) -0.019(4) -0.009(4) C4C 0.051(6) 0.018(3) 0.042(5) 0.005(3) 0.002(4) -0.006(3) C5C 0.070(7) 0.043(5) 0.050(5) 0.004(4) -0.014(5) 0.002(5) C6C 0.039(5) 0.031(4) 0.031(4) -0.002(3) 0.004(4) 0.006(3) C7C 0.037(5) 0.038(4) 0.054(5) 0.005(4) -0.016(4) 0.012(3) C8C 0.050(5) 0.028(4) 0.053(5) 0.007(4) -0.025(4) 0.007(4) C9C 0.034(5) 0.052(5) 0.030(4) -0.002(4) -0.009(3) 0.005(4) C10C 0.084(7) 0.025(4) 0.050(5) 0.021(3) 0.012(5) 0.012(4) C11C 0.030(4) 0.047(4) 0.035(4) 0.003(3) 0.006(3) 0.022(4) C12C 0.026(4) 0.034(4) 0.045(5) -0.001(3) 0.008(4) 0.016(3) C13C 0.025(4) 0.024(4) 0.071(6) -0.002(4) -0.006(4) 0.000(3) C14C 0.042(5) 0.032(4) 0.081(6) 0.003(4) 0.012(5) -0.003(4) C15C 0.026(4) 0.037(4) 0.032(4) 0.010(3) 0.016(3) -0.005(3) C16C 0.041(5) 0.041(5) 0.059(6) 0.011(4) -0.005(4) 0.013(4) C17C 0.038(5) 0.041(5) 0.060(6) 0.020(4) -0.009(4) 0.009(4) C18C 0.045(5) 0.037(4) 0.049(5) 0.010(4) 0.014(4) -0.001(4) C19C 0.051(6) 0.108(8) 0.068(6) 0.035(6) -0.025(5) -0.001(6) C1D 0.040(5) 0.069(6) 0.059(6) -0.010(5) 0.006(4) 0.001(5) C2D 0.041(5) 0.074(6) 0.079(6) 0.017(5) -0.024(5) 0.010(5) C3D 0.056(6) 0.039(5) 0.062(6) -0.012(4) -0.020(4) 0.006(4) C4D 0.049(5) 0.033(4) 0.053(5) -0.009(4) -0.008(4) -0.023(4) C5D 0.057(6) 0.028(4) 0.052(5) -0.003(4) 0.001(4) -0.004(4) C6D 0.054(6) 0.039(5) 0.043(5) 0.003(4) -0.006(4) -0.016(4) C7D 0.065(7) 0.048(5) 0.053(6) -0.005(4) 0.013(5) -0.002(5) C8D 0.044(5) 0.054(5) 0.050(5) 0.004(4) -0.022(4) 0.022(4) C9D 0.070(6) 0.031(4) 0.055(5) -0.010(4) -0.003(4) -0.026(4) C10D 0.015(3) 0.033(4) 0.043(4) -0.025(3) -0.003(3) -0.006(3) C11D 0.056(6) 0.052(6) 0.096(8) -0.005(5) -0.008(6) 0.023(5) C12D 0.039(5) 0.035(4) 0.055(5) -0.010(4) 0.014(4) -0.011(4) C13D 0.039(6) 0.049(5) 0.052(5) 0.003(4) -0.004(4) -0.007(4) C14D 0.063(7) 0.039(5) 0.083(7) -0.011(5) -0.007(5) -0.026(5) C15D 0.057(6) 0.049(5) 0.092(7) 0.003(5) 0.000(6) -0.007(5) C16D 0.026(4) 0.034(4) 0.052(5) 0.002(4) 0.017(4) 0.006(3) C17D 0.049(6) 0.060(6) 0.060(6) 0.004(5) -0.005(5) -0.007(5) C18D 0.021(4) 0.040(4) 0.042(5) 0.004(4) 0.007(3) 0.005(3) C19D 0.040(5) 0.049(5) 0.036(4) -0.002(4) 0.014(4) -0.008(4) C20D 0.047(6) 0.054(6) 0.077(7) 0.000(5) -0.018(5) -0.001(5) N1A 0.031(4) 0.049(4) 0.049(4) 0.008(3) -0.007(3) 0.003(3) N1B 0.061(5) 0.028(4) 0.069(5) -0.006(3) -0.013(4) -0.005(3) N1C 0.024(3) 0.020(3) 0.027(3) 0.002(2) -0.012(3) -0.011(2) N1D 0.029(4) 0.029(3) 0.053(4) 0.001(3) -0.003(3) -0.003(3) O1A 0.035(4) 0.028(3) 0.083(4) 0.001(3) -0.011(3) 0.008(3) O2A 0.051(4) 0.048(4) 0.085(5) -0.002(3) -0.013(4) -0.003(3) O3A 0.042(4) 0.037(3) 0.047(3) 0.003(3) -0.007(3) 0.000(3) O4A 0.041(4) 0.041(3) 0.065(4) -0.002(3) -0.013(3) 0.004(3) O1B 0.043(4) 0.049(4) 0.070(4) -0.001(3) -0.012(3) -0.001(3) O2B 0.035(3) 0.042(3) 0.058(4) -0.002(3) -0.004(3) 0.003(3) O3B 0.069(5) 0.028(3) 0.108(5) 0.007(3) -0.032(4) 0.019(3) O4B 0.047(4) 0.076(4) 0.051(4) -0.016(3) -0.017(3) -0.008(3) O1C 0.051(4) 0.036(3) 0.059(4) 0.005(3) -0.011(3) -0.010(3) O2C 0.094(6) 0.082(5) 0.098(6) -0.007(4) -0.016(5) 0.011(5) O3C 0.045(4) 0.049(4) 0.103(5) -0.002(4) -0.019(4) -0.013(3) O4C 0.037(4) 0.075(4) 0.070(4) 0.011(4) -0.017(3) 0.004(3) O1D 0.047(4) 0.027(3) 0.058(4) 0.000(3) -0.011(3) -0.003(3) O2D 0.085(5) 0.025(3) 0.086(5) 0.002(3) -0.022(4) -0.006(3) O3D 0.026(3) 0.039(3) 0.052(3) -0.006(3) -0.006(2) 0.008(2) O4D 0.030(3) 0.048(3) 0.079(4) -0.005(3) -0.014(3) -0.001(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 C41 C9C 1.368(10) . ? C41 O2C 1.381(11) . ? C41 H41 0.9300 . ? C1A C2A 1.542(12) . ? C1A H1A1 0.9600 . ? C1A H1A2 0.9600 . ? C1A H1A3 0.9600 . ? C2A O1A 1.413(10) . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? C3A C4A 1.363(12) . ? C3A O1A 1.381(10) . ? C3A C8A 1.383(12) . ? C4A C5A 1.404(12) . ? C4A H4A 0.9300 . ? C5A C6A 1.348(12) . ? C5A H5A 0.9300 . ? C6A C7A 1.410(11) . ? C6A C9A 1.492(12) . ? C7A C8A 1.390(12) . ? C7A H7A 0.9300 . ? C8A H8A 0.9300 . ? C9A O2A 1.230(11) . ? C9A C10A 1.475(12) . ? C10A N1A 1.308(10) . ? C10A O3A 1.377(10) . ? C11A O3A 1.335(9) . ? C11A C12A 1.353(12) . ? C11A C13A 1.482(11) . ? C12A N1A 1.335(10) . ? C12A H12A 0.9300 . ? C13A C18A 1.332(11) . ? C13A C14A 1.404(11) . ? C14A C15A 1.355(11) . ? C14A H14A 0.9300 . ? C15A C16A 1.357(11) . ? C15A H15A 0.9300 . ? C16A O4A 1.351(10) . ? C16A C17A 1.405(11) . ? C17A C18A 1.397(11) . ? C17A H17A 0.9300 . ? C18A H18A 0.9300 . ? C19A O4A 1.407(10) . ? C19A C20A 1.538(11) . ? C19A H19A 0.9700 . ? C19A H19B 0.9700 . ? C20A H20A 0.9600 . ? C20A H20B 0.9600 . ? C20A H20C 0.9600 . ? C1B C2B 1.475(12) . ? C1B H1B1 0.9600 . ? C1B H1B2 0.9600 . ? C1B H1B3 0.9600 . ? C2B O1B 1.459(10) . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ? C3B O1B 1.379(10) . ? C3B C4B 1.365(13) . ? C3B C8B 1.407(12) . ? C4B C5B 1.359(12) . ? C4B H4B 0.9300 . ? C5B C6B 1.454(11) . ? C5B H5B 0.9300 . ? C6B C7B 1.337(12) . ? C6B C9B 1.426(12) . ? C7B C8B 1.433(12) . ? C7B H7B 0.9300 . ? C8B H8B 0.9300 . ? C9B C10B 1.335(12) . ? C9B O2B 1.412(10) . ? C10B N1B 1.426(11) . ? C10B H10B 0.9300 . ? C11B N1B 1.275(11) . ? C11B O2B 1.355(10) . ? C11B C12B 1.493(11) . ? C12B O3B 1.222(10) . ? C12B C13B 1.467(12) . ? C13B C14B 1.367(11) . ? C13B C18B 1.432(11) . ? C14B C15B 1.361(12) . ? C14B H14B 0.9300 . ? C15B C16B 1.397(10) . ? C15B H15B 0.9300 . ? C16B O4B 1.357(10) . ? C16B C17B 1.402(11) . ? C17B C18B 1.345(12) . ? C17B H17B 0.9300 . ? C18B H18B 0.9300 . ? C19B O4B 1.451(9) . ? C19B C20B 1.497(13) . ? C19B H19C 0.9700 . ? C19B H19D 0.9700 . ? C20B H20D 0.9600 . ? C20B H20E 0.9600 . ? C20B H20F 0.9600 . ? C1C C2C 1.529(12) . ? C1C H1C1 0.9600 . ? C1C H1C2 0.9600 . ? C1C H1C3 0.9600 . ? C2C O1C 1.400(10) . ? C2C H2C1 0.9700 . ? C2C H2C2 0.9700 . ? C3C C4C 1.356(12) . ? C3C C8C 1.374(11) . ? C3C O1C 1.412(9) . ? C4C C5C 1.383(12) . ? C4C H4C 0.9300 . ? C5C C6C 1.399(11) . ? C5C H5C 0.9300 . ? C6C C7C 1.407(11) . ? C6C C9C 1.458(11) . ? C7C C8C 1.387(11) . ? C7C H7C 0.9300 . ? C8C H8C 0.9300 . ? C9C N1C 1.375(10) . ? C10C N1C 1.257(10) . ? C10C O2C 1.297(10) . ? C10C C11C 1.565(11) . ? C11C O3C 1.196(10) . ? C11C C12C 1.474(11) . ? C12C C13C 1.384(11) . ? C12C C17C 1.389(11) . ? C13C C14C 1.313(12) . ? C13C H13C 0.9300 . ? C14C C15C 1.455(11) . ? C14C H14C 0.9300 . ? C15C C16C 1.351(11) . ? C15C O4C 1.368(9) . ? C16C C17C 1.368(12) . ? C16C H16C 0.9300 . ? C17C H17C 0.9300 . ? C18C O4C 1.390(10) . ? C18C C19C 1.507(12) . ? C18C H18C 0.9700 . ? C18C H18D 0.9700 . ? C19C H19E 0.9600 . ? C19C H19F 0.9600 . ? C19C H19G 0.9600 . ? C1D C2D 1.501(12) . ? C1D H1D1 0.9600 . ? C1D H1D2 0.9600 . ? C1D H1D3 0.9600 . ? C2D O1D 1.492(11) . ? C2D H2D1 0.9700 . ? C2D H2D2 0.9700 . ? C3D C8D 1.304(12) . ? C3D O1D 1.349(10) . ? C3D C4D 1.430(12) . ? C4D C5D 1.399(12) . ? C4D H4D 0.9300 . ? C5D C6D 1.408(11) . ? C5D H5D 0.9300 . ? C6D C7D 1.390(13) . ? C6D C9D 1.494(12) . ? C7D C8D 1.446(12) . ? C7D H7D 0.9300 . ? C8D H8D 0.9300 . ? C9D O2D 1.255(9) . ? C9D C10D 1.385(12) . ? C10D N1D 1.320(9) . ? C10D O3D 1.439(8) . ? C11D C12D 1.330(12) . ? C11D N1D 1.390(11) . ? C11D H11D 0.9300 . ? C12D O3D 1.336(10) . ? C12D C13D 1.467(12) . ? C13D C14D 1.353(12) . ? C13D C18D 1.377(11) . ? C14D C15D 1.385(13) . ? C14D H14D 0.9300 . ? C15D C16D 1.410(12) . ? C15D H15D 0.9300 . ? C16D O4D 1.316(10) . ? C16D C17D 1.408(12) . ? C17D C18D 1.383(11) . ? C17D H17D 0.9300 . ? C18D H18E 0.9300 . ? C19D C20D 1.475(12) . ? C19D O4D 1.481(10) . ? C19D H19H 0.9700 . ? C19D H19I 0.9700 . ? C20D H20G 0.9600 . ? C20D H20H 0.9600 . ? C20D H20I 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 C9C C41 O2C 108.4(7) . . ? C9C C41 H41 125.8 . . ? O2C C41 H41 125.8 . . ? C2A C1A H1A1 109.4 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C2A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? O1A C2A C1A 107.4(7) . . ? O1A C2A H2A1 110.2 . . ? C1A C2A H2A1 110.3 . . ? O1A C2A H2A2 110.3 . . ? C1A C2A H2A2 110.2 . . ? H2A1 C2A H2A2 108.5 . . ? C4A C3A O1A 124.3(8) . . ? C4A C3A C8A 122.2(8) . . ? O1A C3A C8A 113.5(8) . . ? C3A C4A C5A 117.2(8) . . ? C3A C4A H4A 121.4 . . ? C5A C4A H4A 121.4 . . ? C6A C5A C4A 123.2(8) . . ? C6A C5A H5A 118.4 . . ? C4A C5A H5A 118.4 . . ? C5A C6A C7A 118.2(8) . . ? C5A C6A C9A 118.1(8) . . ? C7A C6A C9A 123.6(8) . . ? C8A C7A C6A 119.9(8) . . ? C8A C7A H7A 120.1 . . ? C6A C7A H7A 120.0 . . ? C3A C8A C7A 119.0(8) . . ? C3A C8A H8A 120.5 . . ? C7A C8A H8A 120.5 . . ? O2A C9A C10A 116.3(8) . . ? O2A C9A C6A 120.4(8) . . ? C10A C9A C6A 123.2(8) . . ? N1A C10A O3A 110.0(7) . . ? N1A C10A C9A 132.3(8) . . ? O3A C10A C9A 117.3(7) . . ? O3A C11A C12A 107.9(7) . . ? O3A C11A C13A 114.8(7) . . ? C12A C11A C13A 137.1(7) . . ? N1A C12A C11A 109.0(7) . . ? N1A C12A H12A 125.5 . . ? C11A C12A H12A 125.5 . . ? C18A C13A C14A 117.2(7) . . ? C18A C13A C11A 120.1(8) . . ? C14A C13A C11A 122.7(7) . . ? C15A C14A C13A 120.0(7) . . ? C15A C14A H14A 120.0 . . ? C13A C14A H14A 120.0 . . ? C16A C15A C14A 123.8(8) . . ? C16A C15A H15A 118.1 . . ? C14A C15A H15A 118.1 . . ? O4A C16A C15A 127.1(7) . . ? O4A C16A C17A 116.4(7) . . ? C15A C16A C17A 116.5(8) . . ? C16A C17A C18A 119.1(7) . . ? C16A C17A H17A 120.4 . . ? C18A C17A H17A 120.5 . . ? C13A C18A C17A 123.3(8) . . ? C13A C18A H18A 118.4 . . ? C17A C18A H18A 118.3 . . ? O4A C19A C20A 106.5(7) . . ? O4A C19A H19A 110.4 . . ? C20A C19A H19A 110.4 . . ? O4A C19A H19B 110.4 . . ? C20A C19A H19B 110.5 . . ? H19A C19A H19B 108.6 . . ? C19A C20A H20A 109.5 . . ? C19A C20A H20B 109.4 . . ? H20A C20A H20B 109.5 . . ? C19A C20A H20C 109.5 . . ? H20A C20A H20C 109.5 . . ? H20B C20A H20C 109.5 . . ? C2B C1B H1B1 109.5 . . ? C2B C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? C2B C1B H1B3 109.4 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? O1B C2B C1B 108.0(7) . . ? O1B C2B H2B1 110.1 . . ? C1B C2B H2B1 110.1 . . ? O1B C2B H2B2 110.1 . . ? C1B C2B H2B2 110.1 . . ? H2B1 C2B H2B2 108.4 . . ? O1B C3B C4B 115.8(8) . . ? O1B C3B C8B 122.2(9) . . ? C4B C3B C8B 122.0(8) . . ? C5B C4B C3B 121.4(9) . . ? C5B C4B H4B 119.3 . . ? C3B C4B H4B 119.3 . . ? C4B C5B C6B 119.1(9) . . ? C4B C5B H5B 120.5 . . ? C6B C5B H5B 120.4 . . ? C7B C6B C9B 119.9(8) . . ? C7B C6B C5B 118.4(8) . . ? C9B C6B C5B 121.7(8) . . ? C6B C7B C8B 123.4(8) . . ? C6B C7B H7B 118.3 . . ? C8B C7B H7B 118.3 . . ? C3B C8B C7B 115.5(9) . . ? C3B C8B H8B 122.3 . . ? C7B C8B H8B 122.2 . . ? C10B C9B O2B 105.1(7) . . ? C10B C9B C6B 136.5(8) . . ? O2B C9B C6B 118.2(8) . . ? C9B C10B N1B 112.3(7) . . ? C9B C10B H10B 123.8 . . ? N1B C10B H10B 123.9 . . ? N1B C11B O2B 117.2(8) . . ? N1B C11B C12B 129.9(8) . . ? O2B C11B C12B 112.7(8) . . ? O3B C12B C13B 122.2(7) . . ? O3B C12B C11B 117.7(8) . . ? C13B C12B C11B 119.9(7) . . ? C14B C13B C18B 117.1(8) . . ? C14B C13B C12B 127.8(7) . . ? C18B C13B C12B 114.9(8) . . ? C15B C14B C13B 122.1(7) . . ? C15B C14B H14B 118.9 . . ? C13B C14B H14B 118.9 . . ? C14B C15B C16B 121.4(8) . . ? C14B C15B H15B 119.3 . . ? C16B C15B H15B 119.3 . . ? O4B C16B C15B 117.5(7) . . ? O4B C16B C17B 125.9(7) . . ? C15B C16B C17B 116.5(8) . . ? C18B C17B C16B 122.3(7) . . ? C18B C17B H17B 118.8 . . ? C16B C17B H17B 118.8 . . ? C17B C18B C13B 120.3(8) . . ? C17B C18B H18B 119.8 . . ? C13B C18B H18B 119.8 . . ? O4B C19B C20B 105.9(8) . . ? O4B C19B H19C 110.5 . . ? C20B C19B H19C 110.6 . . ? O4B C19B H19D 110.6 . . ? C20B C19B H19D 110.5 . . ? H19C C19B H19D 108.7 . . ? C19B C20B H20D 109.4 . . ? C19B C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? C19B C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? C2C C1C H1C1 109.5 . . ? C2C C1C H1C2 109.4 . . ? H1C1 C1C H1C2 109.5 . . ? C2C C1C H1C3 109.5 . . ? H1C1 C1C H1C3 109.5 . . ? H1C2 C1C H1C3 109.5 . . ? O1C C2C C1C 109.2(8) . . ? O1C C2C H2C1 109.8 . . ? C1C C2C H2C1 109.8 . . ? O1C C2C H2C2 109.9 . . ? C1C C2C H2C2 109.9 . . ? H2C1 C2C H2C2 108.3 . . ? C4C C3C C8C 121.3(8) . . ? C4C C3C O1C 125.0(7) . . ? C8C C3C O1C 113.7(8) . . ? C3C C4C C5C 120.3(7) . . ? C3C C4C H4C 119.8 . . ? C5C C4C H4C 119.9 . . ? C4C C5C C6C 119.2(8) . . ? C4C C5C H5C 120.4 . . ? C6C C5C H5C 120.4 . . ? C5C C6C C7C 120.4(8) . . ? C5C C6C C9C 119.0(8) . . ? C7C C6C C9C 120.5(7) . . ? C8C C7C C6C 118.0(7) . . ? C8C C7C H7C 121.0 . . ? C6C C7C H7C 121.0 . . ? C3C C8C C7C 120.7(8) . . ? C3C C8C H8C 119.6 . . ? C7C C8C H8C 119.7 . . ? C41 C9C N1C 106.2(7) . . ? C41 C9C C6C 136.3(8) . . ? N1C C9C C6C 117.5(7) . . ? N1C C10C O2C 117.7(8) . . ? N1C C10C C11C 118.1(7) . . ? O2C C10C C11C 124.1(9) . . ? O3C C11C C12C 122.8(8) . . ? O3C C11C C10C 113.9(8) . . ? C12C C11C C10C 123.4(7) . . ? C13C C12C C17C 115.2(7) . . ? C13C C12C C11C 116.7(7) . . ? C17C C12C C11C 128.0(7) . . ? C14C C13C C12C 125.4(7) . . ? C14C C13C H13C 117.3 . . ? C12C C13C H13C 117.3 . . ? C13C C14C C15C 118.2(8) . . ? C13C C14C H14C 120.9 . . ? C15C C14C H14C 120.9 . . ? C16C C15C O4C 118.3(7) . . ? C16C C15C C14C 117.6(7) . . ? O4C C15C C14C 124.1(7) . . ? C15C C16C C17C 121.6(8) . . ? C15C C16C H16C 119.2 . . ? C17C C16C H16C 119.2 . . ? C16C C17C C12C 121.9(8) . . ? C16C C17C H17C 119.1 . . ? C12C C17C H17C 119.0 . . ? O4C C18C C19C 108.2(7) . . ? O4C C18C H18C 110.1 . . ? C19C C18C H18C 110.0 . . ? O4C C18C H18D 110.1 . . ? C19C C18C H18D 110.1 . . ? H18C C18C H18D 108.4 . . ? C18C C19C H19E 109.5 . . ? C18C C19C H19F 109.5 . . ? H19E C19C H19F 109.5 . . ? C18C C19C H19G 109.5 . . ? H19E C19C H19G 109.5 . . ? H19F C19C H19G 109.5 . . ? C2D C1D H1D1 109.5 . . ? C2D C1D H1D2 109.5 . . ? H1D1 C1D H1D2 109.5 . . ? C2D C1D H1D3 109.5 . . ? H1D1 C1D H1D3 109.5 . . ? H1D2 C1D H1D3 109.5 . . ? O1D C2D C1D 105.3(7) . . ? O1D C2D H2D1 110.7 . . ? C1D C2D H2D1 110.7 . . ? O1D C2D H2D2 110.7 . . ? C1D C2D H2D2 110.7 . . ? H2D1 C2D H2D2 108.8 . . ? C8D C3D O1D 125.8(8) . . ? C8D C3D C4D 120.8(8) . . ? O1D C3D C4D 113.4(7) . . ? C5D C4D C3D 119.6(7) . . ? C5D C4D H4D 120.2 . . ? C3D C4D H4D 120.2 . . ? C4D C5D C6D 119.6(8) . . ? C4D C5D H5D 120.2 . . ? C6D C5D H5D 120.2 . . ? C7D C6D C5D 119.7(8) . . ? C7D C6D C9D 118.1(7) . . ? C5D C6D C9D 122.2(8) . . ? C6D C7D C8D 119.0(8) . . ? C6D C7D H7D 120.5 . . ? C8D C7D H7D 120.5 . . ? C3D C8D C7D 121.3(8) . . ? C3D C8D H8D 119.4 . . ? C7D C8D H8D 119.4 . . ? O2D C9D C10D 119.2(8) . . ? O2D C9D C6D 118.0(8) . . ? C10D C9D C6D 122.7(6) . . ? N1D C10D C9D 135.0(7) . . ? N1D C10D O3D 110.3(7) . . ? C9D C10D O3D 114.7(6) . . ? C12D C11D N1D 110.4(8) . . ? C12D C11D H11D 124.8 . . ? N1D C11D H11D 124.8 . . ? C11D C12D O3D 109.7(8) . . ? C11D C12D C13D 133.8(9) . . ? O3D C12D C13D 116.5(6) . . ? C14D C13D C18D 115.8(8) . . ? C14D C13D C12D 122.4(8) . . ? C18D C13D C12D 121.7(8) . . ? C13D C14D C15D 124.9(8) . . ? C13D C14D H14D 117.6 . . ? C15D C14D H14D 117.6 . . ? C14D C15D C16D 118.8(9) . . ? C14D C15D H15D 120.6 . . ? C16D C15D H15D 120.6 . . ? O4D C16D C17D 125.4(7) . . ? O4D C16D C15D 117.3(8) . . ? C17D C16D C15D 117.3(8) . . ? C18D C17D C16D 120.0(8) . . ? C18D C17D H17D 120.0 . . ? C16D C17D H17D 120.0 . . ? C13D C18D C17D 123.1(8) . . ? C13D C18D H18E 118.4 . . ? C17D C18D H18E 118.5 . . ? C20D C19D O4D 105.6(7) . . ? C20D C19D H19H 110.6 . . ? O4D C19D H19H 110.6 . . ? C20D C19D H19I 110.6 . . ? O4D C19D H19I 110.6 . . ? H19H C19D H19I 108.8 . . ? C19D C20D H20G 109.5 . . ? C19D C20D H20H 109.5 . . ? H20G C20D H20H 109.5 . . ? C19D C20D H20I 109.4 . . ? H20G C20D H20I 109.5 . . ? H20H C20D H20I 109.5 . . ? C10A N1A C12A 107.2(8) . . ? C11B N1B C10B 101.2(8) . . ? C10C N1C C9C 105.2(6) . . ? C10D N1D C11D 105.1(7) . . ? C3A O1A C2A 116.6(7) . . ? C11A O3A C10A 105.8(6) . . ? C16A O4A C19A 118.2(6) . . ? C3B O1B C2B 117.3(7) . . ? C11B O2B C9B 104.0(7) . . ? C16B O4B C19B 118.1(7) . . ? C2C O1C C3C 117.5(7) . . ? C10C O2C C41 102.5(8) . . ? C15C O4C C18C 119.8(7) . . ? C3D O1D C2D 115.8(6) . . ? C12D O3D C10D 104.6(6) . . ? C16D O4D C19D 117.1(7) . . ? 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 O1A C3A C4A C5A 179.3(8) . . . . ? C8A C3A C4A C5A 1.3(14) . . . . ? C3A C4A C5A C6A -1.1(15) . . . . ? C4A C5A C6A C7A 3.1(14) . . . . ? C4A C5A C6A C9A 179.9(8) . . . . ? C5A C6A C7A C8A -5.3(12) . . . . ? C9A C6A C7A C8A 178.1(7) . . . . ? C4A C3A C8A C7A -3.6(14) . . . . ? O1A C3A C8A C7A 178.2(7) . . . . ? C6A C7A C8A C3A 5.6(12) . . . . ? C5A C6A C9A O2A 4.2(13) . . . . ? C7A C6A C9A O2A -179.2(8) . . . . ? C5A C6A C9A C10A -178.9(8) . . . . ? C7A C6A C9A C10A -2.3(13) . . . . ? O2A C9A C10A N1A -177.9(9) . . . . ? C6A C9A C10A N1A 5.1(14) . . . . ? O2A C9A C10A O3A -4.7(11) . . . . ? C6A C9A C10A O3A 178.2(7) . . . . ? O3A C11A C12A N1A 1.6(10) . . . . ? C13A C11A C12A N1A 177.8(8) . . . . ? O3A C11A C13A C18A -174.0(7) . . . . ? C12A C11A C13A C18A 10.0(14) . . . . ? O3A C11A C13A C14A 4.0(10) . . . . ? C12A C11A C13A C14A -172.0(10) . . . . ? C18A C13A C14A C15A -1.0(12) . . . . ? C11A C13A C14A C15A -179.0(7) . . . . ? C13A C14A C15A C16A 1.6(13) . . . . ? C14A C15A C16A O4A 178.2(8) . . . . ? C14A C15A C16A C17A -0.4(13) . . . . ? O4A C16A C17A C18A 180.0(7) . . . . ? C15A C16A C17A C18A -1.2(13) . . . . ? C14A C13A C18A C17A -0.6(13) . . . . ? C11A C13A C18A C17A 177.4(8) . . . . ? C16A C17A C18A C13A 1.8(14) . . . . ? O1B C3B C4B C5B 179.0(8) . . . . ? C8B C3B C4B C5B -1.3(15) . . . . ? C3B C4B C5B C6B 1.5(15) . . . . ? C4B C5B C6B C7B 0.4(13) . . . . ? C4B C5B C6B C9B 177.7(8) . . . . ? C9B C6B C7B C8B -179.9(7) . . . . ? C5B C6B C7B C8B -2.5(14) . . . . ? O1B C3B C8B C7B 179.0(7) . . . . ? C4B C3B C8B C7B -0.6(13) . . . . ? C6B C7B C8B C3B 2.6(13) . . . . ? C7B C6B C9B C10B 174.6(10) . . . . ? C5B C6B C9B C10B -2.6(16) . . . . ? C7B C6B C9B O2B -11.3(12) . . . . ? C5B C6B C9B O2B 171.4(7) . . . . ? O2B C9B C10B N1B 2.8(9) . . . . ? C6B C9B C10B N1B 177.4(9) . . . . ? N1B C11B C12B O3B -178.4(11) . . . . ? O2B C11B C12B O3B -3.3(12) . . . . ? N1B C11B C12B C13B 6.0(14) . . . . ? O2B C11B C12B C13B -179.0(7) . . . . ? O3B C12B C13B C14B 176.1(9) . . . . ? C11B C12B C13B C14B -8.4(13) . . . . ? O3B C12B C13B C18B 0.7(13) . . . . ? C11B C12B C13B C18B 176.2(7) . . . . ? C18B C13B C14B C15B -5.0(12) . . . . ? C12B C13B C14B C15B 179.7(8) . . . . ? C13B C14B C15B C16B 5.3(13) . . . . ? C14B C15B C16B O4B 177.7(7) . . . . ? C14B C15B C16B C17B -2.9(12) . . . . ? O4B C16B C17B C18B 179.9(8) . . . . ? C15B C16B C17B C18B 0.6(11) . . . . ? C16B C17B C18B C13B -0.5(13) . . . . ? C14B C13B C18B C17B 2.6(12) . . . . ? C12B C13B C18B C17B 178.5(7) . . . . ? C8C C3C C4C C5C -2.7(14) . . . . ? O1C C3C C4C C5C 176.8(8) . . . . ? C3C C4C C5C C6C 4.5(13) . . . . ? C4C C5C C6C C7C -3.8(13) . . . . ? C4C C5C C6C C9C 179.0(7) . . . . ? C5C C6C C7C C8C 1.4(12) . . . . ? C9C C6C C7C C8C 178.5(8) . . . . ? C4C C3C C8C C7C 0.1(14) . . . . ? O1C C3C C8C C7C -179.4(8) . . . . ? C6C C7C C8C C3C 0.5(13) . . . . ? O2C C41 C9C N1C 0.5(9) . . . . ? O2C C41 C9C C6C -179.8(9) . . . . ? C5C C6C C9C C41 -174.0(9) . . . . ? C7C C6C C9C C41 8.8(15) . . . . ? C5C C6C C9C N1C 5.7(11) . . . . ? C7C C6C C9C N1C -171.4(7) . . . . ? N1C C10C C11C O3C -2.1(11) . . . . ? O2C C10C C11C O3C 179.5(9) . . . . ? N1C C10C C11C C12C 178.4(7) . . . . ? O2C C10C C11C C12C 0.0(13) . . . . ? O3C C11C C12C C13C 0.9(12) . . . . ? C10C C11C C12C C13C -179.6(7) . . . . ? O3C C11C C12C C17C -176.2(9) . . . . ? C10C C11C C12C C17C 3.3(12) . . . . ? C17C C12C C13C C14C -4.0(13) . . . . ? C11C C12C C13C C14C 178.5(8) . . . . ? C12C C13C C14C C15C 4.8(13) . . . . ? C13C C14C C15C C16C -2.9(11) . . . . ? C13C C14C C15C O4C 178.9(7) . . . . ? O4C C15C C16C C17C 178.9(7) . . . . ? C14C C15C C16C C17C 0.6(12) . . . . ? C15C C16C C17C C12C 0.1(14) . . . . ? C13C C12C C17C C16C 1.3(13) . . . . ? C11C C12C C17C C16C 178.5(8) . . . . ? C8D C3D C4D C5D -0.8(14) . . . . ? O1D C3D C4D C5D 179.1(7) . . . . ? C3D C4D C5D C6D 0.2(13) . . . . ? C4D C5D C6D C7D 2.0(13) . . . . ? C4D C5D C6D C9D 179.2(8) . . . . ? C5D C6D C7D C8D -3.5(13) . . . . ? C9D C6D C7D C8D 179.2(7) . . . . ? O1D C3D C8D C7D 179.3(8) . . . . ? C4D C3D C8D C7D -0.9(14) . . . . ? C6D C7D C8D C3D 3.0(14) . . . . ? C7D C6D C9D O2D -4.1(13) . . . . ? C5D C6D C9D O2D 178.7(9) . . . . ? C7D C6D C9D C10D 175.7(8) . . . . ? C5D C6D C9D C10D -1.5(13) . . . . ? O2D C9D C10D N1D 179.2(9) . . . . ? C6D C9D C10D N1D -0.6(15) . . . . ? O2D C9D C10D O3D 0.9(12) . . . . ? C6D C9D C10D O3D -178.9(7) . . . . ? N1D C11D C12D O3D 0.9(11) . . . . ? N1D C11D C12D C13D -179.8(8) . . . . ? C11D C12D C13D C14D -5.5(16) . . . . ? O3D C12D C13D C14D 173.8(8) . . . . ? C11D C12D C13D C18D 172.1(10) . . . . ? O3D C12D C13D C18D -8.6(12) . . . . ? C18D C13D C14D C15D 1.4(15) . . . . ? C12D C13D C14D C15D 179.1(9) . . . . ? C13D C14D C15D C16D 0.7(16) . . . . ? C14D C15D C16D O4D -180.0(8) . . . . ? C14D C15D C16D C17D -0.7(14) . . . . ? O4D C16D C17D C18D 177.8(8) . . . . ? C15D C16D C17D C18D -1.5(13) . . . . ? C14D C13D C18D C17D -3.6(13) . . . . ? C12D C13D C18D C17D 178.6(8) . . . . ? C16D C17D C18D C13D 3.8(13) . . . . ? O3A C10A N1A C12A 2.2(9) . . . . ? C9A C10A N1A C12A 175.7(8) . . . . ? C11A C12A N1A C10A -2.4(10) . . . . ? O2B C11B N1B C10B 3.6(11) . . . . ? C12B C11B N1B C10B 178.5(9) . . . . ? C9B C10B N1B C11B -3.9(10) . . . . ? O2C C10C N1C C9C -1.0(10) . . . . ? C11C C10C N1C C9C -179.5(7) . . . . ? C41 C9C N1C C10C 0.2(9) . . . . ? C6C C9C N1C C10C -179.6(7) . . . . ? C9D C10D N1D C11D -177.3(10) . . . . ? O3D C10D N1D C11D 1.1(9) . . . . ? C12D C11D N1D C10D -1.3(10) . . . . ? C4A C3A O1A C2A -1.1(13) . . . . ? C8A C3A O1A C2A 177.1(7) . . . . ? C1A C2A O1A C3A -176.1(7) . . . . ? C12A C11A O3A C10A -0.3(8) . . . . ? C13A C11A O3A C10A -177.4(6) . . . . ? N1A C10A O3A C11A -1.2(8) . . . . ? C9A C10A O3A C11A -175.8(6) . . . . ? C15A C16A O4A C19A -0.1(12) . . . . ? C17A C16A O4A C19A 178.5(7) . . . . ? C20A C19A O4A C16A -177.1(7) . . . . ? C4B C3B O1B C2B -179.3(8) . . . . ? C8B C3B O1B C2B 1.0(12) . . . . ? C1B C2B O1B C3B 176.3(7) . . . . ? N1B C11B O2B C9B -2.1(11) . . . . ? C12B C11B O2B C9B -177.8(7) . . . . ? C10B C9B O2B C11B -0.6(9) . . . . ? C6B C9B O2B C11B -176.4(7) . . . . ? C15B C16B O4B C19B -174.8(7) . . . . ? C17B C16B O4B C19B 5.8(11) . . . . ? C20B C19B O4B C16B 175.2(7) . . . . ? C1C C2C O1C C3C -176.5(7) . . . . ? C4C C3C O1C C2C 1.4(13) . . . . ? C8C C3C O1C C2C -179.0(8) . . . . ? N1C C10C O2C C41 1.2(11) . . . . ? C11C C10C O2C C41 179.7(8) . . . . ? C9C C41 O2C C10C -0.9(10) . . . . ? C16C C15C O4C C18C 177.1(7) . . . . ? C14C C15C O4C C18C -4.7(11) . . . . ? C19C C18C O4C C15C -174.3(7) . . . . ? C8D C3D O1D C2D 5.3(13) . . . . ? C4D C3D O1D C2D -174.5(8) . . . . ? C1D C2D O1D C3D 176.4(7) . . . . ? C11D C12D O3D C10D -0.2(9) . . . . ? C13D C12D O3D C10D -179.6(6) . . . . ? N1D C10D O3D C12D -0.6(8) . . . . ? C9D C10D O3D C12D 178.1(7) . . . . ? C17D C16D O4D C19D 4.2(12) . . . . ? C15D C16D O4D C19D -176.6(7) . . . . ? C20D C19D O4D C16D 177.0(7) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.172 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.042