Electronic Supplementary Material for CrystEngComm This journal is (c) The royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1350 _publ_section_title ; Monitoring reaction centers and molecules during an enantioselective photoreaction in a crystal ; _publ_section_title_footnote ; Part 9 of the series "Monitoring structural transformations in crystals" ; _publ_contact_author_name 'Ilona Turowska-Tyrk' _publ_contact_author_address ; Department of Chemistry Wroclaw University of Technology Wybrzeze Wyspianskiego 27 Wroclaw 50-370 POLAND ; _publ_contact_author_email ILONA.TUROWSKA-TYRK@PWR.WROC.PL _publ_requested_journal 'Cryst Eng. Comm.' loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Turowska-Tyrk, Ilona' ; ? ; ; Department of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland ; 'Bakowicz, Julia' ; ? ; ; Department of Chemistry, Wroclaw University of Technology, Wybrzeze Wyspianskiego 27, 50-370 Wroclaw, Poland ; 'Scheffer, John R.' ; ? ; ; Department of Chemistry, University of British Columbia, 6174 University Blvd., Vancouver, British Columbia, Canada, V6T 1Z3 ; 'Wujiong Xia.' ; ? ; ; Department of Chemistry, University of British Columbia, 6174 University Blvd., Vancouver, British Columbia, Canada, V6T 1Z3 ; #====================================================================== data_0.0%P _database_code_depnum_ccdc_archive 'CCDC 608915' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.0884(16) _cell_length_b 17.675(4) _cell_length_c 19.404(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2088.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 18 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.175 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9482 _exptl_absorpt_correction_T_max 0.9773 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11199 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3661 _reflns_number_gt 3008 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SXELXL97 (Sheldrick, 1997)' _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^)+(0.0458P)^2^+0.2337P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3661 _refine_ls_number_parameters 369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1007 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 C1R C 0.8269(4) 0.97321(14) 0.48728(11) 0.0560(6) Uani 1 1 d . . . C2R C 1.0466(5) 0.9341(2) 0.48412(15) 0.0758(8) Uani 1 1 d . . . C3R C 1.0130(5) 0.8655(2) 0.46137(16) 0.0852(9) Uani 1 1 d . . . C4R C 0.7717(4) 0.85605(13) 0.44875(13) 0.0644(7) Uani 1 1 d . . . C5R C 0.6639(7) 0.85518(19) 0.52065(14) 0.0791(8) Uani 1 1 d . . . C6R C 0.7022(5) 0.93573(17) 0.54667(13) 0.0701(7) Uani 1 1 d . . . C7R C 0.7100(4) 0.93672(11) 0.42554(10) 0.0480(5) Uani 1 1 d . . . C8R C 0.7913(4) 0.95903(12) 0.35609(11) 0.0525(5) Uani 1 1 d . . . C9R C 0.6859(3) 0.92715(11) 0.29312(10) 0.0427(5) Uani 1 1 d . . . C10R C 0.7979(4) 0.93130(12) 0.23098(11) 0.0479(5) Uani 1 1 d . . . C11R C 0.7077(4) 0.90203(12) 0.17152(11) 0.0460(5) Uani 1 1 d . . . C12R C 0.5007(3) 0.87012(10) 0.17228(10) 0.0408(4) Uani 1 1 d . . . C13R C 0.3868(4) 0.86738(13) 0.23402(11) 0.0485(5) Uani 1 1 d . . . C14R C 0.4776(4) 0.89491(13) 0.29392(11) 0.0494(5) Uani 1 1 d . . . C15R C 0.4023(4) 0.83690(12) 0.10803(11) 0.0464(5) Uani 1 1 d . . . C16R C 0.7766(4) 0.65502(12) 0.10324(10) 0.0475(5) Uani 1 1 d . . . C17R C 0.7306(3) 0.67365(12) 0.17864(10) 0.0470(5) Uani 1 1 d . . . C18R C 0.9404(5) 0.69035(19) 0.21820(12) 0.0651(7) Uani 1 1 d . . . C19R C 0.8942(6) 0.7090(2) 0.29365(12) 0.0801(9) Uani 1 1 d . . . C20R C 0.7702(7) 0.6457(2) 0.32781(15) 0.0936(10) Uani 1 1 d . . . C21R C 0.5622(7) 0.6281(3) 0.28898(15) 0.1006(12) Uani 1 1 d . . . C22R C 0.6069(5) 0.60980(19) 0.21371(14) 0.0725(8) Uani 1 1 d . . . C23R C 0.5753(6) 0.6297(2) 0.06258(15) 0.0756(8) Uani 1 1 d . . . O1R O 0.9428(4) 1.00336(12) 0.34954(9) 0.0952(7) Uani 1 1 d . . . O2R O 0.2068(3) 0.81778(11) 0.10938(8) 0.0731(5) Uani 1 1 d . . . O3R O 0.5275(2) 0.82976(9) 0.05645(7) 0.0537(4) Uani 1 1 d . . . N1R N 0.8675(3) 0.72269(10) 0.06665(9) 0.0419(4) Uani 1 1 d . . . H1R H 0.842(4) 1.0287(15) 0.4908(12) 0.070(7) Uiso 1 1 d . . . H2R H 1.174(6) 0.9594(19) 0.5034(15) 0.105(10) Uiso 1 1 d . . . H3R H 1.129(6) 0.824(2) 0.4592(19) 0.120(11) Uiso 1 1 d . . . H4R H 0.720(4) 0.8157(16) 0.4174(14) 0.086(8) Uiso 1 1 d . . . H5R1 H 0.508(6) 0.8437(17) 0.5158(16) 0.095(10) Uiso 1 1 d . . . H5R2 H 0.734(5) 0.8194(17) 0.5456(15) 0.088(9) Uiso 1 1 d . . . H6R1 H 0.782(5) 0.9369(15) 0.5879(15) 0.084(8) Uiso 1 1 d . . . H6R2 H 0.558(5) 0.9639(17) 0.5557(15) 0.091(9) Uiso 1 1 d . . . H7R H 0.545(4) 0.9426(13) 0.4296(12) 0.062(6) Uiso 1 1 d . . . H10R H 0.953(4) 0.9535(12) 0.2282(11) 0.058(6) Uiso 1 1 d . . . H11R H 0.786(3) 0.9043(11) 0.1303(10) 0.045(5) Uiso 1 1 d . . . H13R H 0.239(4) 0.8438(13) 0.2341(12) 0.071(7) Uiso 1 1 d . . . H14R H 0.399(4) 0.8915(13) 0.3359(12) 0.060(7) Uiso 1 1 d . . . H16R H 0.894(4) 0.6144(14) 0.1021(12) 0.065(7) Uiso 1 1 d . . . H17R H 0.647(4) 0.7221(14) 0.1816(12) 0.065(7) Uiso 1 1 d . . . H18A H 1.022(5) 0.732(2) 0.1959(16) 0.106(11) Uiso 1 1 d . . . H18B H 1.032(5) 0.6392(17) 0.2150(13) 0.077(8) Uiso 1 1 d . . . H19A H 1.033(6) 0.7187(19) 0.3163(17) 0.104(11) Uiso 1 1 d . . . H19B H 0.809(5) 0.7589(17) 0.2984(14) 0.088(9) Uiso 1 1 d . . . H20A H 0.863(7) 0.601(2) 0.3263(19) 0.126(14) Uiso 1 1 d . . . H20B H 0.741(5) 0.6581(17) 0.3758(18) 0.106(10) Uiso 1 1 d . . . H21A H 0.463(7) 0.674(2) 0.296(2) 0.137(16) Uiso 1 1 d . . . H21B H 0.499(5) 0.5837(19) 0.3126(16) 0.099(10) Uiso 1 1 d . . . H22A H 0.703(5) 0.5619(19) 0.2076(15) 0.098(10) Uiso 1 1 d . . . H22B H 0.465(6) 0.5998(18) 0.1894(15) 0.103(10) Uiso 1 1 d . . . H23A H 0.614(5) 0.6281(16) 0.0123(16) 0.090(9) Uiso 1 1 d . . . H23B H 0.456(6) 0.665(2) 0.0718(18) 0.109(12) Uiso 1 1 d . . . H23C H 0.543(5) 0.579(2) 0.0797(16) 0.104(10) Uiso 1 1 d . . . H1R1 H 0.916(4) 0.7066(13) 0.0200(13) 0.065(7) Uiso 1 1 d . . . H1R2 H 0.993(4) 0.7476(14) 0.0913(13) 0.075(8) Uiso 1 1 d . . . H1R3 H 0.763(4) 0.7609(13) 0.0650(11) 0.050(6) Uiso 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 C1R 0.0643(14) 0.0575(14) 0.0460(12) -0.0078(10) -0.0125(10) -0.0001(11) C2R 0.0579(15) 0.097(2) 0.0727(17) -0.0017(16) -0.0186(13) 0.0037(15) C3R 0.080(2) 0.090(2) 0.086(2) -0.0028(17) -0.0091(16) 0.0314(18) C4R 0.0864(18) 0.0513(13) 0.0555(14) -0.0038(11) -0.0074(13) 0.0009(13) C5R 0.107(3) 0.079(2) 0.0520(15) 0.0105(14) -0.0088(16) -0.0089(18) C6R 0.0806(18) 0.0892(19) 0.0405(13) -0.0046(13) -0.0074(13) 0.0001(16) C7R 0.0530(12) 0.0491(11) 0.0418(11) -0.0079(9) -0.0056(10) -0.0024(10) C8R 0.0609(13) 0.0500(12) 0.0468(11) -0.0052(9) -0.0049(11) -0.0095(11) C9R 0.0480(11) 0.0407(10) 0.0393(10) -0.0035(8) -0.0060(9) -0.0022(9) C10R 0.0452(11) 0.0526(11) 0.0459(11) -0.0026(9) -0.0021(10) -0.0096(10) C11R 0.0492(11) 0.0524(11) 0.0363(10) -0.0011(9) 0.0031(10) -0.0073(10) C12R 0.0427(10) 0.0405(10) 0.0391(10) -0.0037(8) -0.0033(9) -0.0010(8) C13R 0.0416(11) 0.0589(13) 0.0449(11) -0.0075(10) 0.0007(9) -0.0092(10) C14R 0.0485(12) 0.0605(13) 0.0393(11) -0.0056(10) 0.0054(10) -0.0084(10) C15R 0.0518(12) 0.0473(11) 0.0399(10) -0.0026(9) -0.0078(10) -0.0016(10) C16R 0.0611(13) 0.0424(11) 0.0389(10) 0.0008(8) 0.0037(10) -0.0003(10) C17R 0.0564(12) 0.0463(11) 0.0381(10) 0.0023(9) 0.0057(9) 0.0078(10) C18R 0.0735(16) 0.0820(18) 0.0397(12) -0.0008(12) -0.0016(11) -0.0142(15) C19R 0.106(2) 0.099(2) 0.0359(12) -0.0037(14) -0.0035(15) -0.0023(19) C20R 0.121(3) 0.118(3) 0.0420(14) 0.0175(17) 0.0090(18) 0.008(2) C21R 0.101(3) 0.147(3) 0.0545(16) 0.0194(19) 0.0242(18) -0.019(3) C22R 0.0764(18) 0.085(2) 0.0555(15) 0.0175(14) 0.0120(14) -0.0165(17) C23R 0.094(2) 0.0770(19) 0.0558(16) -0.0005(15) -0.0054(15) -0.0409(18) O1R 0.1205(16) 0.1101(15) 0.0551(10) -0.0045(10) -0.0077(10) -0.0741(14) O2R 0.0555(10) 0.1093(14) 0.0543(9) -0.0132(9) -0.0059(8) -0.0281(10) O3R 0.0573(8) 0.0676(9) 0.0363(7) -0.0082(7) -0.0059(7) 0.0041(8) N1R 0.0404(9) 0.0527(10) 0.0328(9) -0.0037(8) 0.0009(8) -0.0019(8) _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 C1R C2R 1.507(4) . ? C1R C6R 1.531(4) . ? C1R C7R 1.536(3) . ? C2R C3R 1.306(4) . ? C3R C4R 1.499(4) . ? C4R C5R 1.542(4) . ? C4R C7R 1.542(3) . ? C5R C6R 1.528(4) . ? C7R C8R 1.489(3) . ? C8R O1R 1.217(3) . ? C8R C9R 1.491(3) . ? C9R C10R 1.387(3) . ? C9R C14R 1.391(3) . ? C10R C11R 1.379(3) . ? C11R C12R 1.381(3) . ? C12R C13R 1.385(3) . ? C12R C15R 1.503(3) . ? C13R C14R 1.376(3) . ? C15R O2R 1.237(3) . ? C15R O3R 1.264(3) . ? C16R N1R 1.497(3) . ? C16R C23R 1.525(3) . ? C16R C17R 1.526(3) . ? C17R C22R 1.518(3) . ? C17R C18R 1.519(3) . ? C18R C19R 1.527(4) . ? C19R C20R 1.503(5) . ? C20R C21R 1.506(5) . ? C21R C22R 1.521(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 C2R C1R C6R 105.8(2) . . ? C2R C1R C7R 100.8(2) . . ? C6R C1R C7R 100.12(19) . . ? C3R C2R C1R 107.5(3) . . ? C2R C3R C4R 108.2(3) . . ? C3R C4R C5R 105.7(2) . . ? C3R C4R C7R 100.6(2) . . ? C5R C4R C7R 99.8(2) . . ? C6R C5R C4R 103.0(2) . . ? C5R C6R C1R 103.3(2) . . ? C8R C7R C1R 116.16(19) . . ? C8R C7R C4R 115.37(18) . . ? C1R C7R C4R 92.72(18) . . ? O1R C8R C7R 121.13(19) . . ? O1R C8R C9R 118.94(19) . . ? C7R C8R C9R 119.92(18) . . ? C10R C9R C14R 118.66(19) . . ? C10R C9R C8R 118.76(18) . . ? C14R C9R C8R 122.56(19) . . ? C11R C10R C9R 120.80(18) . . ? C10R C11R C12R 120.5(2) . . ? C11R C12R C13R 118.73(18) . . ? C11R C12R C15R 120.98(18) . . ? C13R C12R C15R 120.28(16) . . ? C14R C13R C12R 121.13(19) . . ? C13R C14R C9R 120.1(2) . . ? O2R C15R O3R 124.70(19) . . ? O2R C15R C12R 118.21(19) . . ? O3R C15R C12R 117.08(17) . . ? N1R C16R C23R 106.64(19) . . ? N1R C16R C17R 110.51(16) . . ? C23R C16R C17R 114.3(2) . . ? C22R C17R C18R 109.6(2) . . ? C22R C17R C16R 111.14(19) . . ? C18R C17R C16R 111.85(19) . . ? C17R C18R C19R 111.8(2) . . ? C20R C19R C18R 110.8(3) . . ? C19R C20R C21R 110.8(3) . . ? C20R C21R C22R 112.0(3) . . ? C17R C22R C21R 111.2(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.169 _refine_diff_density_min -0.123 _refine_diff_density_rms 0.039 #===END data_10.0%P _database_code_depnum_ccdc_archive 'CCDC 608916' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.0982(14) _cell_length_b 17.667(4) _cell_length_c 19.405(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2090.6(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9483 _exptl_absorpt_correction_T_max 0.9774 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11223 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3644 _reflns_number_gt 3023 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0716P)^2^+0.0606P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.017(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3644 _refine_ls_number_parameters 354 _refine_ls_number_restraints 195 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.044 _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 C1R C 0.8295(6) 0.97375(19) 0.48740(17) 0.0623(12) Uani 0.900(4) 1 d PD A 1 H1R H 0.8327 1.0292 0.4878 0.075 Uiso 0.900(4) 1 calc PR A 1 C2R C 1.0475(4) 0.9353(2) 0.48492(15) 0.0793(8) Uani 0.900(4) 1 d PD A 1 H2R H 1.1815 0.9561 0.4977 0.095 Uiso 0.900(4) 1 calc PR A 1 C3R C 1.0147(7) 0.8667(2) 0.4614(2) 0.0905(13) Uani 0.900(4) 1 d PDU A 1 H3R H 1.1226 0.8304 0.4540 0.109 Uiso 0.900(4) 1 calc PR A 1 C4R C 0.7732(4) 0.85638(12) 0.44841(12) 0.0664(7) Uani 0.900(4) 1 d PD A 1 H4R H 0.7320 0.8152 0.4171 0.080 Uiso 0.900(4) 1 calc PR A 1 C5R C 0.6666(6) 0.85532(18) 0.52037(15) 0.0837(9) Uani 0.900(4) 1 d PDU A 1 H5R1 H 0.5115 0.8435 0.5173 0.100 Uiso 0.900(4) 1 calc PR A 1 H5R2 H 0.7374 0.8185 0.5501 0.100 Uiso 0.900(4) 1 calc PR A 1 C6R C 0.7024(8) 0.9358(2) 0.54694(14) 0.0739(11) Uani 0.900(4) 1 d PDU A 1 H6R1 H 0.7878 0.9358 0.5891 0.089 Uiso 0.900(4) 1 calc PR A 1 H6R2 H 0.5638 0.9612 0.5552 0.089 Uiso 0.900(4) 1 calc PR A 1 C7R C 0.7126(6) 0.93682(16) 0.42537(11) 0.0509(6) Uani 0.900(4) 1 d PD A 1 H7R H 0.5538 0.9445 0.4288 0.061 Uiso 0.900(4) 1 calc PR A 1 C8R C 0.7922(5) 0.9597(2) 0.35585(14) 0.0559(8) Uani 0.900(4) 1 d PD A 1 C9R C 0.6885(7) 0.9274(2) 0.29282(13) 0.0460(12) Uani 0.900(4) 1 d PD A 1 C10R C 0.8020(6) 0.92948(19) 0.23111(13) 0.0492(8) Uani 0.900(4) 1 d PD A 1 H10R H 0.9411 0.9510 0.2297 0.059 Uiso 0.900(4) 1 calc PR A 1 C11R C 0.7125(6) 0.9004(2) 0.17194(12) 0.0455(7) Uani 0.900(4) 1 d PD A 1 H11R H 0.7931 0.9011 0.1312 0.055 Uiso 0.900(4) 1 calc PR A 1 C12R C 0.5043(8) 0.8700(4) 0.17228(16) 0.0441(17) Uani 0.900(4) 1 d PD A 1 C13R C 0.3877(6) 0.8690(2) 0.23346(15) 0.0522(9) Uani 0.900(4) 1 d PDU A 1 H13R H 0.2462 0.8493 0.2340 0.063 Uiso 0.900(4) 1 calc PR A 1 C14R C 0.4775(5) 0.8964(2) 0.29325(12) 0.0505(8) Uani 0.900(4) 1 d PD A 1 H14R H 0.3980 0.8945 0.3341 0.061 Uiso 0.900(4) 1 calc PR A 1 C15R C 0.4079(7) 0.8361(3) 0.10793(18) 0.0485(13) Uani 0.900(4) 1 d PD A 1 C16R C 0.7728(6) 0.65584(19) 0.10318(14) 0.0482(8) Uani 0.900(4) 1 d PDU A 1 H16R H 0.8807 0.6148 0.1008 0.058 Uiso 0.900(4) 1 calc PR A 1 C17R C 0.7290(7) 0.67322(19) 0.17870(12) 0.0467(8) Uani 0.900(4) 1 d PD A 1 H17R H 0.6362 0.7184 0.1810 0.056 Uiso 0.900(4) 1 calc PR A 1 C18R C 0.9381(6) 0.6893(2) 0.21822(14) 0.0659(9) Uani 0.900(4) 1 d PD A 1 H18A H 1.0133 0.7317 0.1970 0.079 Uiso 0.900(4) 1 calc PR A 1 H18B H 1.0338 0.6456 0.2154 0.079 Uiso 0.900(4) 1 calc PR A 1 C19R C 0.8945(7) 0.7075(2) 0.29355(13) 0.0786(9) Uani 0.900(4) 1 d PD A 1 H19A H 1.0327 0.7151 0.3173 0.094 Uiso 0.900(4) 1 calc PR A 1 H19B H 0.8106 0.7540 0.2968 0.094 Uiso 0.900(4) 1 calc PR A 1 C20R C 0.7696(7) 0.6442(3) 0.32751(14) 0.0891(10) Uani 0.900(4) 1 d PD A 1 H20A H 0.8612 0.5994 0.3295 0.107 Uiso 0.900(4) 1 calc PR A 1 H20B H 0.7330 0.6585 0.3744 0.107 Uiso 0.900(4) 1 calc PR A 1 C21R C 0.5638(6) 0.6265(3) 0.28878(14) 0.0994(12) Uani 0.900(4) 1 d PDU A 1 H21A H 0.4648 0.6694 0.2918 0.119 Uiso 0.900(4) 1 calc PR A 1 H21B H 0.4922 0.5834 0.3100 0.119 Uiso 0.900(4) 1 calc PR A 1 C22R C 0.6082(6) 0.6091(2) 0.21352(15) 0.0718(8) Uani 0.900(4) 1 d PDU A 1 H22A H 0.6949 0.5632 0.2102 0.086 Uiso 0.900(4) 1 calc PR A 1 H22B H 0.4702 0.6003 0.1900 0.086 Uiso 0.900(4) 1 calc PR A 1 C23R C 0.5720(6) 0.6320(2) 0.06282(16) 0.0709(8) Uani 0.900(4) 1 d PD A 1 H23A H 0.6136 0.6202 0.0163 0.106 Uiso 0.900(4) 1 calc PR A 1 H23B H 0.4673 0.6726 0.0626 0.106 Uiso 0.900(4) 1 calc PR A 1 H23C H 0.5078 0.5882 0.0840 0.106 Uiso 0.900(4) 1 calc PR A 1 O1R O 0.9421(4) 1.00415(13) 0.34917(9) 0.0963(9) Uani 0.900(4) 1 d PD A 1 O2R O 0.2120(6) 0.8171(3) 0.1091(2) 0.0783(17) Uani 0.900(4) 1 d PD A 1 O3R O 0.5330(6) 0.8284(2) 0.05681(16) 0.0575(9) Uani 0.900(4) 1 d PD A 1 N1R N 0.8667(8) 0.7236(2) 0.06764(18) 0.0454(9) Uani 0.900(4) 1 d PDU A 1 H1R1 H 0.8881 0.7130 0.0233 0.068 Uiso 0.900(4) 1 calc PR A 1 H1R2 H 0.9940 0.7359 0.0871 0.068 Uiso 0.900(4) 1 calc PR A 1 H1R3 H 0.7739 0.7623 0.0714 0.068 Uiso 0.900(4) 1 calc PR A 1 C1P C 0.798(4) 0.9742(13) 0.4770(9) 0.042(9) Uiso 0.100(4) 1 d PD A 2 H1P H 0.8000 1.0296 0.4791 0.050 Uiso 0.100(4) 1 calc PR A 2 C2P C 1.015(3) 0.9424(13) 0.4460(9) 0.084(9) Uiso 0.100(4) 1 d PD A 2 H2P H 1.1402 0.9734 0.4600 0.100 Uiso 0.100(4) 1 calc PR A 2 C3P C 1.051(6) 0.8611(18) 0.465(2) 0.097(10) Uiso 0.100(4) 1 d PDU A 2 H3P H 1.1704 0.8366 0.4457 0.116 Uiso 0.100(4) 1 calc PR A 2 C4P C 0.925(4) 0.8211(13) 0.5078(15) 0.105(10) Uiso 0.100(4) 1 d PD A 2 H4P H 0.9622 0.7710 0.5169 0.125 Uiso 0.100(4) 1 calc PR A 2 C5P C 0.726(5) 0.8541(16) 0.5417(18) 0.103(10) Uiso 0.100(4) 1 d PDU A 2 H5P1 H 0.7098 0.8328 0.5875 0.123 Uiso 0.100(4) 1 calc PR A 2 H5P2 H 0.5965 0.8407 0.5153 0.123 Uiso 0.100(4) 1 calc PR A 2 C6P C 0.743(6) 0.9397(17) 0.5469(10) 0.082(10) Uiso 0.100(4) 1 d PDU A 2 H6P1 H 0.8561 0.9530 0.5799 0.099 Uiso 0.100(4) 1 calc PR A 2 H6P2 H 0.6049 0.9602 0.5633 0.099 Uiso 0.100(4) 1 calc PR A 2 C7P C 0.640(3) 0.9461(19) 0.4230(9) 0.062(10) Uiso 0.100(4) 1 d PD A 2 H7P H 0.4939 0.9324 0.4293 0.074 Uiso 0.100(4) 1 calc PR A 2 C8P C 0.753(3) 0.945(2) 0.3643(8) 0.073(15) Uiso 0.100(4) 1 d PD A 2 C9P C 0.656(3) 0.9200(13) 0.2955(8) 0.040(12) Uiso 0.100(4) 1 d PD A 2 C10P C 0.753(3) 0.9423(14) 0.2336(9) 0.032(8) Uiso 0.100(4) 1 d PD A 2 H10P H 0.8739 0.9747 0.2341 0.039 Uiso 0.100(4) 1 calc PR A 2 C11P C 0.671(4) 0.9164(15) 0.1713(9) 0.035(9) Uiso 0.100(4) 1 d PD A 2 H11P H 0.7415 0.9284 0.1303 0.043 Uiso 0.100(4) 1 calc PR A 2 C12P C 0.481(6) 0.872(3) 0.1702(10) 0.030(12) Uiso 0.100(4) 1 d PD A 2 C13P C 0.379(5) 0.853(2) 0.2319(11) 0.046(5) Uiso 0.100(4) 1 d PDU A 2 H13P H 0.2487 0.8257 0.2312 0.055 Uiso 0.100(4) 1 calc PR A 2 C14P C 0.469(4) 0.8750(17) 0.2941(10) 0.049(10) Uiso 0.100(4) 1 d PD A 2 H14P H 0.4051 0.8594 0.3352 0.059 Uiso 0.100(4) 1 calc PR A 2 C15P C 0.382(4) 0.846(2) 0.1025(11) 0.036(11) Uiso 0.100(4) 1 d PD A 2 C16P C 0.825(4) 0.6517(14) 0.1045(10) 0.030(6) Uiso 0.100(4) 1 d PDU A 2 H16P H 0.9510 0.6174 0.1062 0.036 Uiso 0.100(4) 1 calc PR A 2 C17P C 0.780(4) 0.6803(17) 0.1781(10) 0.044(10) Uiso 0.100(4) 1 d PD A 2 H17P H 0.6945 0.7269 0.1732 0.053 Uiso 0.100(4) 1 calc PR A 2 C18P C 0.990(3) 0.7021(16) 0.2159(11) 0.039(7) Uiso 0.100(4) 1 d PD A 2 H18C H 1.0621 0.7424 0.1907 0.047 Uiso 0.100(4) 1 calc PR A 2 H18D H 1.0877 0.6588 0.2166 0.047 Uiso 0.100(4) 1 calc PR A 2 C19P C 0.949(4) 0.7285(16) 0.2907(12) 0.062(9) Uiso 0.100(4) 1 d PD A 2 H19C H 1.0869 0.7420 0.3126 0.075 Uiso 0.100(4) 1 calc PR A 2 H19D H 0.8540 0.7725 0.2912 0.075 Uiso 0.100(4) 1 calc PR A 2 C20P C 0.842(5) 0.663(2) 0.3286(13) 0.084(12) Uiso 0.100(4) 1 d PD A 2 H20C H 0.9332 0.6181 0.3254 0.100 Uiso 0.100(4) 1 calc PR A 2 H20D H 0.8233 0.6755 0.3770 0.100 Uiso 0.100(4) 1 calc PR A 2 C21P C 0.620(5) 0.648(2) 0.2957(14) 0.107(10) Uiso 0.100(4) 1 d PDU A 2 H21C H 0.5307 0.6932 0.2995 0.128 Uiso 0.100(4) 1 calc PR A 2 H21D H 0.5472 0.6077 0.3205 0.128 Uiso 0.100(4) 1 calc PR A 2 C22P C 0.640(6) 0.626(2) 0.2197(14) 0.091(10) Uiso 0.100(4) 1 d PDU A 2 H22C H 0.7028 0.5757 0.2166 0.109 Uiso 0.100(4) 1 calc PR A 2 H22D H 0.4945 0.6241 0.1996 0.109 Uiso 0.100(4) 1 calc PR A 2 C23P C 0.637(4) 0.6106(13) 0.0687(13) 0.052(8) Uiso 0.100(4) 1 d PD A 2 H23D H 0.6790 0.5981 0.0224 0.078 Uiso 0.100(4) 1 calc PR A 2 H23E H 0.5100 0.6428 0.0677 0.078 Uiso 0.100(4) 1 calc PR A 2 H23F H 0.6030 0.5650 0.0934 0.078 Uiso 0.100(4) 1 calc PR A 2 O1P O 0.977(3) 0.9487(13) 0.3712(8) 0.101(7) Uiso 0.100(4) 1 d PD A 2 O2P O 0.192(4) 0.820(2) 0.1030(18) 0.055(10) Uiso 0.100(4) 1 d PD A 2 O3P O 0.511(4) 0.8416(16) 0.0513(12) 0.028(5) Uiso 0.100(4) 1 d PD A 2 N1P N 0.884(6) 0.7180(18) 0.0587(15) 0.027(4) Uiso 0.100(4) 1 d PDU A 2 H1P1 H 0.9783 0.7480 0.0807 0.040 Uiso 0.100(4) 1 calc PR A 2 H1P2 H 0.7636 0.7440 0.0484 0.040 Uiso 0.100(4) 1 calc PR A 2 H1P3 H 0.9457 0.7010 0.0201 0.040 Uiso 0.100(4) 1 calc PR A 2 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 C1R 0.073(2) 0.0615(18) 0.0524(16) -0.0095(12) -0.0178(15) 0.0024(13) C2R 0.0613(14) 0.102(2) 0.0747(19) 0.0006(17) -0.0168(14) 0.0053(15) C3R 0.089(2) 0.097(2) 0.086(2) -0.0024(18) -0.0058(18) 0.037(2) C4R 0.0943(18) 0.0509(13) 0.0539(14) -0.0044(10) -0.0058(12) 0.0011(12) C5R 0.115(2) 0.0837(19) 0.0519(15) 0.0111(14) -0.0070(16) -0.0139(18) C6R 0.085(2) 0.096(2) 0.0407(13) -0.0065(12) -0.0105(12) 0.0025(17) C7R 0.0526(15) 0.0545(14) 0.0454(14) -0.0084(9) -0.0054(11) -0.0014(13) C8R 0.0668(16) 0.0523(16) 0.0485(14) -0.0045(11) -0.0038(12) -0.0085(15) C9R 0.0513(14) 0.0426(15) 0.0442(18) -0.0039(9) -0.0062(10) -0.0042(12) C10R 0.0420(13) 0.0536(17) 0.0518(16) -0.0064(10) -0.0016(11) -0.0043(15) C11R 0.0470(13) 0.0474(16) 0.0420(15) -0.0012(9) 0.0025(10) -0.0019(15) C12R 0.045(2) 0.042(2) 0.045(2) -0.0039(9) -0.0029(10) 0.0007(14) C13R 0.0449(11) 0.059(2) 0.0523(13) -0.0123(12) 0.0041(9) -0.0128(13) C14R 0.0571(17) 0.0530(19) 0.0414(14) -0.0092(10) 0.0086(10) -0.0094(13) C15R 0.0540(17) 0.047(2) 0.0439(17) -0.0027(12) -0.0112(12) 0.0026(15) C16R 0.0558(19) 0.0462(13) 0.0426(13) 0.0020(8) 0.0020(12) 0.0013(14) C17R 0.0518(15) 0.0477(16) 0.0407(14) 0.0036(9) 0.0067(10) 0.0031(13) C18R 0.071(2) 0.085(2) 0.0419(14) 0.0011(12) 0.0014(13) -0.0214(18) C19R 0.102(2) 0.094(2) 0.0399(14) -0.0011(14) -0.0033(14) -0.015(2) C20R 0.107(3) 0.119(3) 0.0422(15) 0.0209(15) 0.0073(16) 0.000(3) C21R 0.099(2) 0.142(3) 0.0571(17) 0.0191(19) 0.0234(17) -0.025(2) C22R 0.0760(18) 0.081(2) 0.0578(15) 0.0180(14) 0.0106(13) -0.0185(16) C23R 0.086(2) 0.0667(18) 0.0602(16) 0.0047(14) -0.0112(15) -0.0305(18) O1R 0.1237(17) 0.1067(17) 0.0586(11) -0.0053(10) -0.0083(10) -0.0744(14) O2R 0.0590(16) 0.117(3) 0.0585(17) -0.0171(13) -0.0088(10) -0.0295(14) O3R 0.0639(14) 0.069(2) 0.0400(11) -0.0083(11) -0.0094(9) 0.0107(13) N1R 0.0445(15) 0.0586(14) 0.0330(13) -0.0058(10) 0.0028(10) -0.0032(11) _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 C1R C2R 1.494(4) . ? C1R C7R 1.544(4) . ? C1R C6R 1.545(4) . ? C2R C3R 1.310(5) . ? C3R C4R 1.505(5) . ? C4R C7R 1.535(4) . ? C4R C5R 1.541(4) . ? C5R C6R 1.528(4) . ? C7R C8R 1.490(4) . ? C8R O1R 1.212(4) . ? C8R C9R 1.491(3) . ? C9R C10R 1.383(4) . ? C9R C14R 1.398(4) . ? C10R C11R 1.371(3) . ? C11R C12R 1.378(4) . ? C12R C13R 1.384(3) . ? C12R C15R 1.504(3) . ? C13R C14R 1.372(3) . ? C15R O2R 1.241(3) . ? C15R O3R 1.259(3) . ? C16R N1R 1.496(3) . ? C16R C23R 1.513(4) . ? C16R C17R 1.521(3) . ? C17R C22R 1.511(4) . ? C17R C18R 1.515(4) . ? C18R C19R 1.520(3) . ? C19R C20R 1.506(5) . ? C20R C21R 1.496(5) . ? C21R C22R 1.517(4) . ? C1P C7P 1.509(10) . ? C1P C6P 1.524(10) . ? C1P C2P 1.557(10) . ? C2P O1P 1.474(10) . ? C2P C3P 1.500(10) . ? C3P C4P 1.330(10) . ? C4P C5P 1.500(10) . ? C5P C6P 1.520(10) . ? C7P C8P 1.331(9) . ? C8P O1P 1.374(9) . ? C8P C9P 1.526(9) . ? C9P C14P 1.391(9) . ? C9P C10P 1.397(9) . ? C10P C11P 1.388(9) . ? C11P C12P 1.394(9) . ? C12P C13P 1.392(9) . ? C12P C15P 1.520(9) . ? C13P C14P 1.383(10) . ? C15P O2P 1.246(10) . ? C15P O3P 1.269(10) . ? C16P N1P 1.514(10) . ? C16P C23P 1.525(10) . ? C16P C17P 1.539(10) . ? C17P C22P 1.517(10) . ? C17P C18P 1.523(10) . ? C18P C19P 1.545(10) . ? C19P C20P 1.522(10) . ? C20P C21P 1.517(10) . ? C21P C22P 1.530(10) . ? 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 C2R C1R C7R 101.2(2) . . ? C2R C1R C6R 105.9(3) . . ? C7R C1R C6R 99.7(2) . . ? C3R C2R C1R 107.2(3) . . ? C2R C3R C4R 108.7(3) . . ? C3R C4R C7R 99.9(2) . . ? C3R C4R C5R 105.2(3) . . ? C7R C4R C5R 100.0(2) . . ? C6R C5R C4R 103.6(2) . . ? C5R C6R C1R 102.9(2) . . ? C8R C7R C4R 115.9(2) . . ? C8R C7R C1R 116.2(2) . . ? C4R C7R C1R 93.0(2) . . ? O1R C8R C7R 121.2(2) . . ? O1R C8R C9R 118.7(3) . . ? C7R C8R C9R 120.0(3) . . ? C10R C9R C14R 118.4(2) . . ? C10R C9R C8R 119.2(3) . . ? C14R C9R C8R 122.4(3) . . ? C11R C10R C9R 121.0(3) . . ? C10R C11R C12R 120.6(2) . . ? C11R C12R C13R 118.9(2) . . ? C11R C12R C15R 120.7(2) . . ? C13R C12R C15R 120.4(3) . . ? C14R C13R C12R 121.0(3) . . ? C13R C14R C9R 120.1(2) . . ? O2R C15R O3R 124.7(3) . . ? O2R C15R C12R 117.9(3) . . ? O3R C15R C12R 117.4(3) . . ? N1R C16R C23R 107.1(2) . . ? N1R C16R C17R 110.5(2) . . ? C23R C16R C17R 114.4(3) . . ? C22R C17R C18R 109.0(2) . . ? C22R C17R C16R 111.4(2) . . ? C18R C17R C16R 112.2(3) . . ? C17R C18R C19R 112.3(3) . . ? C20R C19R C18R 110.6(3) . . ? C21R C20R C19R 111.1(2) . . ? C20R C21R C22R 112.1(3) . . ? C17R C22R C21R 111.4(3) . . ? C7P C1P C6P 110.3(13) . . ? C7P C1P C2P 99.0(9) . . ? C6P C1P C2P 112.8(12) . . ? O1P C2P C3P 109.9(15) . . ? O1P C2P C1P 102.7(9) . . ? C3P C2P C1P 111.9(11) . . ? C4P C3P C2P 125.4(13) . . ? C3P C4P C5P 122.2(13) . . ? C4P C5P C6P 111.1(13) . . ? C5P C6P C1P 110.7(13) . . ? C8P C7P C1P 105.5(10) . . ? C7P C8P O1P 115.6(10) . . ? C7P C8P C9P 123.6(12) . . ? O1P C8P C9P 118.8(11) . . ? C14P C9P C10P 119.5(10) . . ? C14P C9P C8P 120.0(11) . . ? C10P C9P C8P 120.5(11) . . ? C11P C10P C9P 120.1(12) . . ? C10P C11P C12P 120.0(12) . . ? C13P C12P C11P 119.6(11) . . ? C13P C12P C15P 119.3(12) . . ? C11P C12P C15P 121.1(12) . . ? C14P C13P C12P 120.3(12) . . ? C13P C14P C9P 120.2(12) . . ? O2P C15P O3P 124.1(16) . . ? O2P C15P C12P 118.5(14) . . ? O3P C15P C12P 116.6(14) . . ? N1P C16P C23P 106.3(13) . . ? N1P C16P C17P 109.4(14) . . ? C23P C16P C17P 116.5(13) . . ? C22P C17P C18P 112.1(14) . . ? C22P C17P C16P 112.7(13) . . ? C18P C17P C16P 112.5(13) . . ? C17P C18P C19P 113.3(12) . . ? C20P C19P C18P 107.0(13) . . ? C21P C20P C19P 108.1(14) . . ? C20P C21P C22P 112.4(15) . . ? C17P C22P C21P 113.3(14) . . ? C8P O1P C2P 104.4(9) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.141 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.035 #===END data_13.6%P _database_code_depnum_ccdc_archive 'CCDC 608917' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1046(13) _cell_length_b 17.656(4) _cell_length_c 19.423(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2093.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.172 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9483 _exptl_absorpt_correction_T_max 0.9774 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11228 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3650 _reflns_number_gt 2995 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0764P)^2^+0.0335P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3650 _refine_ls_number_parameters 354 _refine_ls_number_restraints 195 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.031 _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 C1R C 0.8307(7) 0.9743(2) 0.48694(17) 0.0636(12) Uani 0.864(4) 1 d PD A 1 H1R H 0.8338 1.0298 0.4874 0.076 Uiso 0.864(4) 1 calc PR A 1 C2R C 1.0483(5) 0.9356(2) 0.48492(16) 0.0817(9) Uani 0.864(4) 1 d PD A 1 H2R H 1.1820 0.9563 0.4981 0.098 Uiso 0.864(4) 1 calc PR A 1 C3R C 1.0159(7) 0.8670(3) 0.4611(2) 0.0931(14) Uani 0.864(4) 1 d PDU A 1 H3R H 1.1241 0.8309 0.4533 0.112 Uiso 0.864(4) 1 calc PR A 1 C4R C 0.7742(4) 0.85631(13) 0.44851(13) 0.0687(8) Uani 0.864(4) 1 d PD A 1 H4R H 0.7328 0.8150 0.4175 0.082 Uiso 0.864(4) 1 calc PR A 1 C5R C 0.6689(7) 0.85557(18) 0.52053(15) 0.0849(10) Uani 0.864(4) 1 d PDU A 1 H5R1 H 0.5140 0.8437 0.5178 0.102 Uiso 0.864(4) 1 calc PR A 1 H5R2 H 0.7401 0.8189 0.5502 0.102 Uiso 0.864(4) 1 calc PR A 1 C6R C 0.7043(8) 0.9358(2) 0.54689(14) 0.0766(12) Uani 0.864(4) 1 d PDU A 1 H6R1 H 0.7902 0.9359 0.5889 0.092 Uiso 0.864(4) 1 calc PR A 1 H6R2 H 0.5657 0.9611 0.5554 0.092 Uiso 0.864(4) 1 calc PR A 1 C7R C 0.7127(6) 0.93709(16) 0.42523(11) 0.0533(6) Uani 0.864(4) 1 d PD A 1 H7R H 0.5541 0.9448 0.4287 0.064 Uiso 0.864(4) 1 calc PR A 1 C8R C 0.7924(6) 0.9599(2) 0.35570(14) 0.0584(8) Uani 0.864(4) 1 d PD A 1 C9R C 0.6885(7) 0.9273(2) 0.29280(14) 0.0470(13) Uani 0.864(4) 1 d PD A 1 C10R C 0.8032(6) 0.9286(2) 0.23140(16) 0.0515(10) Uani 0.864(4) 1 d PD A 1 H10R H 0.9429 0.9496 0.2302 0.062 Uiso 0.864(4) 1 calc PR A 1 C11R C 0.7142(7) 0.8993(2) 0.17220(15) 0.0475(9) Uani 0.864(4) 1 d PD A 1 H11R H 0.7956 0.8993 0.1317 0.057 Uiso 0.864(4) 1 calc PR A 1 C12R C 0.5043(10) 0.8700(5) 0.1724(2) 0.046(2) Uani 0.864(4) 1 d PD A 1 C13R C 0.3875(7) 0.8695(3) 0.23323(17) 0.0550(12) Uani 0.864(4) 1 d PDU A 1 H13R H 0.2458 0.8502 0.2337 0.066 Uiso 0.864(4) 1 calc PR A 1 C14R C 0.4769(5) 0.8971(2) 0.29293(14) 0.0538(9) Uani 0.864(4) 1 d PD A 1 H14R H 0.3965 0.8958 0.3336 0.065 Uiso 0.864(4) 1 calc PR A 1 C15R C 0.4093(7) 0.8357(4) 0.1080(2) 0.0498(14) Uani 0.864(4) 1 d PD A 1 C16R C 0.7721(7) 0.6563(2) 0.10315(16) 0.0504(10) Uani 0.864(4) 1 d PDU A 1 H16R H 0.8786 0.6149 0.1006 0.060 Uiso 0.864(4) 1 calc PR A 1 C17R C 0.7296(8) 0.6732(2) 0.17856(14) 0.0483(9) Uani 0.864(4) 1 d PD A 1 H17R H 0.6361 0.7183 0.1812 0.058 Uiso 0.864(4) 1 calc PR A 1 C18R C 0.9384(7) 0.6894(3) 0.21814(16) 0.0680(11) Uani 0.864(4) 1 d PD A 1 H18A H 1.0132 0.7320 0.1972 0.082 Uiso 0.864(4) 1 calc PR A 1 H18B H 1.0344 0.6457 0.2151 0.082 Uiso 0.864(4) 1 calc PR A 1 C19R C 0.8943(8) 0.7071(3) 0.29351(15) 0.0809(11) Uani 0.864(4) 1 d PD A 1 H19A H 1.0322 0.7148 0.3173 0.097 Uiso 0.864(4) 1 calc PR A 1 H19B H 0.8098 0.7534 0.2970 0.097 Uiso 0.864(4) 1 calc PR A 1 C20R C 0.7703(8) 0.6432(3) 0.32725(16) 0.0916(12) Uani 0.864(4) 1 d PD A 1 H20A H 0.8627 0.5985 0.3291 0.110 Uiso 0.864(4) 1 calc PR A 1 H20B H 0.7334 0.6573 0.3741 0.110 Uiso 0.864(4) 1 calc PR A 1 C21R C 0.5663(7) 0.6253(3) 0.28863(16) 0.1003(13) Uani 0.864(4) 1 d PDU A 1 H21A H 0.4665 0.6679 0.2919 0.120 Uiso 0.864(4) 1 calc PR A 1 H21B H 0.4957 0.5818 0.3096 0.120 Uiso 0.864(4) 1 calc PR A 1 C22R C 0.6103(7) 0.6083(3) 0.21312(17) 0.0741(10) Uani 0.864(4) 1 d PDU A 1 H22A H 0.6978 0.5626 0.2095 0.089 Uiso 0.864(4) 1 calc PR A 1 H22B H 0.4724 0.5994 0.1897 0.089 Uiso 0.864(4) 1 calc PR A 1 C23R C 0.5708(7) 0.6329(2) 0.06287(18) 0.0704(9) Uani 0.864(4) 1 d PD A 1 H23A H 0.6119 0.6210 0.0164 0.106 Uiso 0.864(4) 1 calc PR A 1 H23B H 0.4669 0.6737 0.0627 0.106 Uiso 0.864(4) 1 calc PR A 1 H23C H 0.5060 0.5891 0.0840 0.106 Uiso 0.864(4) 1 calc PR A 1 O1R O 0.9419(4) 1.00428(14) 0.34906(10) 0.0994(9) Uani 0.864(4) 1 d PD A 1 O2R O 0.2134(6) 0.8164(4) 0.1093(2) 0.0812(18) Uani 0.864(4) 1 d PD A 1 O3R O 0.5346(7) 0.8282(3) 0.05702(19) 0.0599(11) Uani 0.864(4) 1 d PD A 1 N1R N 0.8689(10) 0.7237(3) 0.0680(2) 0.0512(15) Uani 0.864(4) 1 d PDU A 1 H1R1 H 0.8903 0.7132 0.0237 0.077 Uiso 0.864(4) 1 calc PR A 1 H1R2 H 0.9963 0.7353 0.0876 0.077 Uiso 0.864(4) 1 calc PR A 1 H1R3 H 0.7777 0.7628 0.0718 0.077 Uiso 0.864(4) 1 calc PR A 1 C1P C 0.791(3) 0.9731(11) 0.4766(8) 0.057(8) Uiso 0.136(4) 1 d PD A 2 H1P H 0.7915 1.0286 0.4777 0.068 Uiso 0.136(4) 1 calc PR A 2 C2P C 1.010(2) 0.9430(9) 0.4463(7) 0.079(6) Uiso 0.136(4) 1 d PD A 2 H2P H 1.1322 0.9759 0.4600 0.094 Uiso 0.136(4) 1 calc PR A 2 C3P C 1.054(5) 0.8629(14) 0.4680(17) 0.108(10) Uiso 0.136(4) 1 d PDU A 2 H3P H 1.1797 0.8397 0.4514 0.129 Uiso 0.136(4) 1 calc PR A 2 C4P C 0.925(3) 0.8227(10) 0.5093(11) 0.097(7) Uiso 0.136(4) 1 d PD A 2 H4P H 0.9545 0.7714 0.5150 0.116 Uiso 0.136(4) 1 calc PR A 2 C5P C 0.735(4) 0.8559(13) 0.5471(14) 0.118(8) Uiso 0.136(4) 1 d PDU A 2 H5P1 H 0.7363 0.8378 0.5943 0.141 Uiso 0.136(4) 1 calc PR A 2 H5P2 H 0.5999 0.8387 0.5259 0.141 Uiso 0.136(4) 1 calc PR A 2 C6P C 0.738(5) 0.9416(13) 0.5474(9) 0.102(10) Uiso 0.136(4) 1 d PDU A 2 H6P1 H 0.8472 0.9591 0.5801 0.122 Uiso 0.136(4) 1 calc PR A 2 H6P2 H 0.5966 0.9604 0.5621 0.122 Uiso 0.136(4) 1 calc PR A 2 C7P C 0.633(2) 0.9447(16) 0.4227(8) 0.079(10) Uiso 0.136(4) 1 d PD A 2 H7P H 0.4872 0.9314 0.4286 0.095 Uiso 0.136(4) 1 calc PR A 2 C8P C 0.750(2) 0.9428(14) 0.3649(7) 0.064(9) Uiso 0.136(4) 1 d PD A 2 C9P C 0.659(3) 0.9190(10) 0.2952(7) 0.049(11) Uiso 0.136(4) 1 d PD A 2 C10P C 0.760(3) 0.9412(12) 0.2340(8) 0.036(7) Uiso 0.136(4) 1 d PD A 2 H10P H 0.8798 0.9736 0.2348 0.043 Uiso 0.136(4) 1 calc PR A 2 C11P C 0.679(3) 0.9144(12) 0.1717(8) 0.032(6) Uiso 0.136(4) 1 d PD A 2 H11P H 0.7529 0.9252 0.1311 0.038 Uiso 0.136(4) 1 calc PR A 2 C12P C 0.488(5) 0.872(3) 0.1695(9) 0.035(12) Uiso 0.136(4) 1 d PD A 2 C13P C 0.379(4) 0.8546(17) 0.2308(9) 0.041(6) Uiso 0.136(4) 1 d PDU A 2 H13P H 0.2457 0.8293 0.2297 0.049 Uiso 0.136(4) 1 calc PR A 2 C14P C 0.470(3) 0.8752(12) 0.2932(8) 0.046(7) Uiso 0.136(4) 1 d PD A 2 H14P H 0.4046 0.8597 0.3340 0.056 Uiso 0.136(4) 1 calc PR A 2 C15P C 0.391(3) 0.846(2) 0.1013(9) 0.041(9) Uiso 0.136(4) 1 d PD A 2 C16P C 0.821(3) 0.6516(12) 0.1044(9) 0.032(5) Uiso 0.136(4) 1 d PDU A 2 H16P H 0.9475 0.6175 0.1047 0.039 Uiso 0.136(4) 1 calc PR A 2 C17P C 0.777(4) 0.6786(16) 0.1786(9) 0.050(9) Uiso 0.136(4) 1 d PD A 2 H17P H 0.6942 0.7260 0.1741 0.060 Uiso 0.136(4) 1 calc PR A 2 C18P C 0.988(3) 0.6995(16) 0.2160(10) 0.051(7) Uiso 0.136(4) 1 d PD A 2 H18C H 1.0600 0.7399 0.1909 0.061 Uiso 0.136(4) 1 calc PR A 2 H18D H 1.0844 0.6560 0.2160 0.061 Uiso 0.136(4) 1 calc PR A 2 C19P C 0.951(4) 0.7254(14) 0.2910(10) 0.066(7) Uiso 0.136(4) 1 d PD A 2 H19C H 1.0898 0.7366 0.3130 0.079 Uiso 0.136(4) 1 calc PR A 2 H19D H 0.8604 0.7705 0.2922 0.079 Uiso 0.136(4) 1 calc PR A 2 C20P C 0.837(4) 0.6604(16) 0.3279(11) 0.080(9) Uiso 0.136(4) 1 d PD A 2 H20C H 0.9221 0.6143 0.3233 0.096 Uiso 0.136(4) 1 calc PR A 2 H20D H 0.8214 0.6719 0.3765 0.096 Uiso 0.136(4) 1 calc PR A 2 C21P C 0.612(4) 0.650(2) 0.2954(12) 0.113(9) Uiso 0.136(4) 1 d PDU A 2 H21C H 0.5304 0.6966 0.2985 0.135 Uiso 0.136(4) 1 calc PR A 2 H21D H 0.5322 0.6111 0.3207 0.135 Uiso 0.136(4) 1 calc PR A 2 C22P C 0.632(5) 0.626(2) 0.2198(12) 0.090(9) Uiso 0.136(4) 1 d PDU A 2 H22C H 0.6912 0.5750 0.2174 0.108 Uiso 0.136(4) 1 calc PR A 2 H22D H 0.4869 0.6249 0.1993 0.108 Uiso 0.136(4) 1 calc PR A 2 C23P C 0.631(3) 0.6123(11) 0.0678(11) 0.056(7) Uiso 0.136(4) 1 d PD A 2 H23D H 0.6737 0.5999 0.0216 0.084 Uiso 0.136(4) 1 calc PR A 2 H23E H 0.5065 0.6455 0.0668 0.084 Uiso 0.136(4) 1 calc PR A 2 H23F H 0.5935 0.5667 0.0921 0.084 Uiso 0.136(4) 1 calc PR A 2 O1P O 0.973(2) 0.9479(10) 0.3716(6) 0.098(5) Uiso 0.136(4) 1 d PD A 2 O2P O 0.198(3) 0.8222(19) 0.1011(15) 0.060(7) Uiso 0.136(4) 1 d PD A 2 O3P O 0.520(4) 0.8398(16) 0.0504(11) 0.036(5) Uiso 0.136(4) 1 d PD A 2 N1P N 0.875(4) 0.7204(13) 0.0609(13) 0.019(4) Uiso 0.136(4) 1 d PDU A 2 H1P1 H 0.9686 0.7499 0.0835 0.028 Uiso 0.136(4) 1 calc PR A 2 H1P2 H 0.7523 0.7463 0.0523 0.028 Uiso 0.136(4) 1 calc PR A 2 H1P3 H 0.9343 0.7056 0.0213 0.028 Uiso 0.136(4) 1 calc PR A 2 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 C1R 0.073(2) 0.062(2) 0.0558(17) -0.0111(12) -0.0191(16) 0.0023(14) C2R 0.0624(15) 0.106(3) 0.076(2) 0.0011(18) -0.0166(15) 0.0047(16) C3R 0.093(3) 0.099(3) 0.088(2) -0.004(2) -0.006(2) 0.036(2) C4R 0.097(2) 0.0535(14) 0.0557(15) -0.0042(11) -0.0053(13) -0.0006(13) C5R 0.118(2) 0.085(2) 0.0519(16) 0.0120(14) -0.0053(17) -0.0170(18) C6R 0.092(2) 0.097(2) 0.0409(14) -0.0067(13) -0.0112(13) 0.0031(18) C7R 0.0576(17) 0.0581(16) 0.0442(15) -0.0108(10) -0.0048(11) -0.0026(14) C8R 0.0699(18) 0.0531(18) 0.0523(15) -0.0036(12) -0.0059(13) -0.0091(16) C9R 0.0522(15) 0.0436(16) 0.045(2) -0.0043(9) -0.0056(10) -0.0040(13) C10R 0.0433(15) 0.0553(19) 0.0559(18) -0.0070(12) -0.0035(12) -0.0032(17) C11R 0.0507(16) 0.0484(19) 0.0434(16) -0.0016(11) 0.0031(11) -0.0003(16) C12R 0.047(3) 0.043(3) 0.048(3) -0.0038(11) -0.0030(11) -0.0016(14) C13R 0.0477(15) 0.060(3) 0.0575(18) -0.0160(13) 0.0059(11) -0.0151(15) C14R 0.0637(19) 0.052(2) 0.0454(15) -0.0109(12) 0.0097(11) -0.0098(15) C15R 0.057(2) 0.048(2) 0.0441(17) -0.0025(15) -0.0114(13) 0.0018(15) C16R 0.056(2) 0.0481(15) 0.0469(15) 0.0031(9) 0.0026(13) 0.0019(15) C17R 0.0531(17) 0.0492(18) 0.0425(16) 0.0040(9) 0.0066(11) 0.0014(15) C18R 0.070(2) 0.090(3) 0.0440(16) 0.0019(13) 0.0003(14) -0.022(2) C19R 0.105(3) 0.097(3) 0.0402(15) -0.0014(16) -0.0037(16) -0.018(2) C20R 0.105(3) 0.124(3) 0.0453(17) 0.0221(17) 0.0087(18) -0.004(3) C21R 0.104(2) 0.140(4) 0.0569(18) 0.018(2) 0.0221(18) -0.028(2) C22R 0.082(2) 0.081(3) 0.0598(17) 0.0175(15) 0.0099(14) -0.0201(18) C23R 0.084(2) 0.0650(19) 0.0617(18) 0.0057(15) -0.0124(16) -0.0268(19) O1R 0.1274(18) 0.1094(18) 0.0614(12) -0.0061(11) -0.0089(11) -0.0749(15) O2R 0.0615(16) 0.122(3) 0.0606(19) -0.0163(17) -0.0117(11) -0.0319(16) O3R 0.0681(15) 0.071(3) 0.0404(13) -0.0073(13) -0.0110(10) 0.0101(14) N1R 0.0512(17) 0.067(2) 0.0358(19) -0.0066(12) 0.0011(11) -0.0046(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 C1R C2R 1.494(4) . ? C1R C7R 1.545(4) . ? C1R C6R 1.553(4) . ? C2R C3R 1.313(5) . ? C3R C4R 1.507(5) . ? C4R C5R 1.540(4) . ? C4R C7R 1.543(4) . ? C5R C6R 1.522(4) . ? C7R C8R 1.491(4) . ? C8R O1R 1.209(4) . ? C8R C9R 1.492(3) . ? C9R C10R 1.383(4) . ? C9R C14R 1.397(5) . ? C10R C11R 1.372(3) . ? C11R C12R 1.382(4) . ? C12R C13R 1.379(4) . ? C12R C15R 1.507(4) . ? C13R C14R 1.371(4) . ? C15R O2R 1.244(3) . ? C15R O3R 1.258(3) . ? C16R N1R 1.494(3) . ? C16R C23R 1.514(4) . ? C16R C17R 1.517(3) . ? C17R C22R 1.515(4) . ? C17R C18R 1.516(5) . ? C18R C19R 1.521(4) . ? C19R C20R 1.508(5) . ? C20R C21R 1.488(5) . ? C21R C22R 1.521(4) . ? C1P C7P 1.509(10) . ? C1P C6P 1.518(10) . ? C1P C2P 1.555(9) . ? C2P O1P 1.472(9) . ? C2P C3P 1.499(10) . ? C3P C4P 1.330(10) . ? C4P C5P 1.493(10) . ? C5P C6P 1.512(10) . ? C7P C8P 1.328(9) . ? C8P O1P 1.373(9) . ? C8P C9P 1.524(9) . ? C9P C14P 1.388(9) . ? C9P C10P 1.395(9) . ? C10P C11P 1.390(9) . ? C11P C12P 1.391(9) . ? C12P C13P 1.394(9) . ? C12P C15P 1.519(9) . ? C13P C14P 1.382(9) . ? C15P O2P 1.248(10) . ? C15P O3P 1.268(10) . ? C16P N1P 1.517(10) . ? C16P C23P 1.526(10) . ? C16P C17P 1.541(10) . ? C17P C22P 1.514(10) . ? C17P C18P 1.522(10) . ? C18P C19P 1.543(10) . ? C19P C20P 1.522(10) . ? C20P C21P 1.520(10) . ? C21P C22P 1.533(10) . ? 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 C2R C1R C7R 101.5(2) . . ? C2R C1R C6R 105.2(3) . . ? C7R C1R C6R 99.4(3) . . ? C3R C2R C1R 107.3(3) . . ? C2R C3R C4R 108.7(3) . . ? C3R C4R C5R 105.2(3) . . ? C3R C4R C7R 99.8(3) . . ? C5R C4R C7R 99.9(2) . . ? C6R C5R C4R 103.8(2) . . ? C5R C6R C1R 103.0(2) . . ? C8R C7R C4R 115.9(2) . . ? C8R C7R C1R 115.8(3) . . ? C4R C7R C1R 93.0(2) . . ? O1R C8R C7R 121.2(2) . . ? O1R C8R C9R 118.9(3) . . ? C7R C8R C9R 119.9(3) . . ? C10R C9R C14R 118.4(2) . . ? C10R C9R C8R 119.0(4) . . ? C14R C9R C8R 122.6(3) . . ? C11R C10R C9R 121.1(3) . . ? C10R C11R C12R 120.3(3) . . ? C13R C12R C11R 119.0(3) . . ? C13R C12R C15R 120.7(3) . . ? C11R C12R C15R 120.3(3) . . ? C14R C13R C12R 121.1(3) . . ? C13R C14R C9R 120.1(3) . . ? O2R C15R O3R 124.9(3) . . ? O2R C15R C12R 117.6(3) . . ? O3R C15R C12R 117.5(3) . . ? N1R C16R C23R 107.6(3) . . ? N1R C16R C17R 110.6(3) . . ? C23R C16R C17R 114.4(3) . . ? C22R C17R C18R 108.8(3) . . ? C22R C17R C16R 111.1(3) . . ? C18R C17R C16R 112.5(3) . . ? C17R C18R C19R 112.2(3) . . ? C20R C19R C18R 110.7(3) . . ? C21R C20R C19R 111.1(3) . . ? C20R C21R C22R 112.3(3) . . ? C17R C22R C21R 111.3(3) . . ? C7P C1P C6P 111.8(13) . . ? C7P C1P C2P 99.9(9) . . ? C6P C1P C2P 113.6(12) . . ? O1P C2P C3P 111.1(14) . . ? O1P C2P C1P 102.8(8) . . ? C3P C2P C1P 111.6(10) . . ? C4P C3P C2P 124.7(12) . . ? C3P C4P C5P 123.1(12) . . ? C4P C5P C6P 112.5(12) . . ? C5P C6P C1P 111.5(12) . . ? C8P C7P C1P 104.7(9) . . ? C7P C8P O1P 116.8(9) . . ? C7P C8P C9P 124.2(11) . . ? O1P C8P C9P 117.7(9) . . ? C14P C9P C10P 120.0(10) . . ? C14P C9P C8P 118.8(10) . . ? C10P C9P C8P 121.3(11) . . ? C11P C10P C9P 119.3(11) . . ? C10P C11P C12P 120.7(11) . . ? C11P C12P C13P 119.2(10) . . ? C11P C12P C15P 120.9(12) . . ? C13P C12P C15P 119.8(11) . . ? C14P C13P C12P 120.1(12) . . ? C13P C14P C9P 120.3(11) . . ? O2P C15P O3P 123.6(15) . . ? O2P C15P C12P 117.9(13) . . ? O3P C15P C12P 117.7(13) . . ? N1P C16P C23P 105.6(12) . . ? N1P C16P C17P 108.1(13) . . ? C23P C16P C17P 116.4(13) . . ? C22P C17P C18P 113.0(13) . . ? C22P C17P C16P 113.9(13) . . ? C18P C17P C16P 112.0(12) . . ? C17P C18P C19P 113.6(12) . . ? C20P C19P C18P 106.7(13) . . ? C21P C20P C19P 108.2(13) . . ? C20P C21P C22P 111.2(14) . . ? C17P C22P C21P 112.6(13) . . ? C8P O1P C2P 104.0(9) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.159 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.036 #===END data_17.8%P _database_code_depnum_ccdc_archive 'CCDC 608918' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1154(13) _cell_length_b 17.642(4) _cell_length_c 19.443(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2097.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.170 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9484 _exptl_absorpt_correction_T_max 0.9774 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11249 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3659 _reflns_number_gt 2915 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.0878P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.018(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3659 _refine_ls_number_parameters 354 _refine_ls_number_restraints 171 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1222 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.068 _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 C1R C 0.8312(8) 0.9748(2) 0.48598(19) 0.0664(14) Uani 0.822(4) 1 d PD A 1 H1R H 0.8344 1.0304 0.4863 0.080 Uiso 0.822(4) 1 calc PR A 1 C2R C 1.0482(6) 0.9361(3) 0.4847(2) 0.0877(11) Uani 0.822(4) 1 d PD A 1 H2R H 1.1809 0.9573 0.4980 0.105 Uiso 0.822(4) 1 calc PR A 1 C3R C 1.0189(9) 0.8665(3) 0.4615(3) 0.0934(19) Uani 0.822(4) 1 d PD A 1 H3R H 1.1271 0.8304 0.4543 0.112 Uiso 0.822(4) 1 calc PR A 1 C4R C 0.7759(5) 0.85649(17) 0.44850(15) 0.0751(10) Uani 0.822(4) 1 d PD A 1 H4R H 0.7344 0.8149 0.4177 0.090 Uiso 0.822(4) 1 calc PR A 1 C5R C 0.6721(8) 0.8556(2) 0.52089(17) 0.0897(11) Uani 0.822(4) 1 d PDU A 1 H5R1 H 0.5177 0.8433 0.5185 0.108 Uiso 0.822(4) 1 calc PR A 1 H5R2 H 0.7447 0.8191 0.5504 0.108 Uiso 0.822(4) 1 calc PR A 1 C6R C 0.7064(11) 0.9362(3) 0.54697(19) 0.0853(17) Uani 0.822(4) 1 d PDU A 1 H6R1 H 0.7933 0.9367 0.5887 0.102 Uiso 0.822(4) 1 calc PR A 1 H6R2 H 0.5678 0.9611 0.5558 0.102 Uiso 0.822(4) 1 calc PR A 1 C7R C 0.7104(7) 0.93748(19) 0.42500(13) 0.0571(8) Uani 0.822(4) 1 d PD A 1 H7R H 0.5521 0.9451 0.4286 0.068 Uiso 0.822(4) 1 calc PR A 1 C8R C 0.7919(7) 0.9601(2) 0.35577(16) 0.0638(10) Uani 0.822(4) 1 d PD A 1 C9R C 0.6882(8) 0.9273(3) 0.29279(17) 0.0502(14) Uani 0.822(4) 1 d PD A 1 C10R C 0.8034(9) 0.9278(3) 0.2318(2) 0.0550(14) Uani 0.822(4) 1 d PD A 1 H10R H 0.9431 0.9486 0.2308 0.066 Uiso 0.822(4) 1 calc PR A 1 C11R C 0.7165(8) 0.8983(3) 0.17256(19) 0.0506(11) Uani 0.822(4) 1 d PD A 1 H11R H 0.7996 0.8973 0.1325 0.061 Uiso 0.822(4) 1 calc PR A 1 C12R C 0.5053(13) 0.8701(6) 0.1722(2) 0.050(3) Uani 0.822(4) 1 d PD A 1 C13R C 0.3880(8) 0.8705(3) 0.2325(2) 0.0598(15) Uani 0.822(4) 1 d PD A 1 H13R H 0.2453 0.8522 0.2326 0.072 Uiso 0.822(4) 1 calc PR A 1 C14R C 0.4776(7) 0.8973(3) 0.29261(17) 0.0584(11) Uani 0.822(4) 1 d PD A 1 H14R H 0.3974 0.8954 0.3332 0.070 Uiso 0.822(4) 1 calc PR A 1 C15R C 0.4117(9) 0.8355(4) 0.1075(2) 0.0508(17) Uani 0.822(4) 1 d PD A 1 C16R C 0.7711(9) 0.6569(3) 0.1029(2) 0.0554(14) Uani 0.822(4) 1 d PD A 1 H16R H 0.8757 0.6150 0.1001 0.066 Uiso 0.822(4) 1 calc PR A 1 C17R C 0.7312(10) 0.6730(3) 0.17846(18) 0.0519(13) Uani 0.822(4) 1 d PD A 1 H17R H 0.6390 0.7183 0.1817 0.062 Uiso 0.822(4) 1 calc PR A 1 C18R C 0.9390(8) 0.6881(4) 0.2178(2) 0.0746(15) Uani 0.822(4) 1 d PD A 1 H18A H 1.0148 0.7307 0.1971 0.090 Uiso 0.822(4) 1 calc PR A 1 H18B H 1.0336 0.6441 0.2145 0.090 Uiso 0.822(4) 1 calc PR A 1 C19R C 0.8961(9) 0.7055(3) 0.29319(18) 0.0849(13) Uani 0.822(4) 1 d PD A 1 H19A H 1.0342 0.7130 0.3168 0.102 Uiso 0.822(4) 1 calc PR A 1 H19B H 0.8123 0.7520 0.2969 0.102 Uiso 0.822(4) 1 calc PR A 1 C20R C 0.7727(9) 0.6420(3) 0.32701(19) 0.0935(14) Uani 0.822(4) 1 d PD A 1 H20A H 0.8640 0.5971 0.3286 0.112 Uiso 0.822(4) 1 calc PR A 1 H20B H 0.7367 0.6561 0.3739 0.112 Uiso 0.822(4) 1 calc PR A 1 C21R C 0.5674(10) 0.6248(4) 0.2884(2) 0.1078(18) Uani 0.822(4) 1 d PD A 1 H21A H 0.4685 0.6676 0.2920 0.129 Uiso 0.822(4) 1 calc PR A 1 H21B H 0.4962 0.5813 0.3090 0.129 Uiso 0.822(4) 1 calc PR A 1 C22R C 0.6119(9) 0.6084(4) 0.2131(2) 0.0747(16) Uani 0.822(4) 1 d PD A 1 H22A H 0.6989 0.5626 0.2094 0.090 Uiso 0.822(4) 1 calc PR A 1 H22B H 0.4743 0.5996 0.1896 0.090 Uiso 0.822(4) 1 calc PR A 1 C23R C 0.5703(8) 0.6342(3) 0.0629(2) 0.0737(11) Uani 0.822(4) 1 d PD A 1 H23A H 0.6109 0.6223 0.0165 0.111 Uiso 0.822(4) 1 calc PR A 1 H23B H 0.4674 0.6752 0.0629 0.111 Uiso 0.822(4) 1 calc PR A 1 H23C H 0.5050 0.5905 0.0840 0.111 Uiso 0.822(4) 1 calc PR A 1 O1R O 0.9419(5) 1.00443(18) 0.34905(12) 0.1075(12) Uani 0.822(4) 1 d PDU A 1 O2R O 0.2165(8) 0.8170(4) 0.1080(3) 0.089(3) Uani 0.822(4) 1 d PD A 1 O3R O 0.5387(9) 0.8282(4) 0.0569(2) 0.0652(16) Uani 0.822(4) 1 d PD A 1 N1R N 0.8713(13) 0.7236(4) 0.0679(3) 0.056(2) Uani 0.822(4) 1 d PDU A 1 H1R1 H 0.8924 0.7129 0.0237 0.084 Uiso 0.822(4) 1 calc PR A 1 H1R2 H 0.9989 0.7344 0.0876 0.084 Uiso 0.822(4) 1 calc PR A 1 H1R3 H 0.7823 0.7633 0.0716 0.084 Uiso 0.822(4) 1 calc PR A 1 C1P C 0.786(3) 0.9729(11) 0.4762(7) 0.078(10) Uiso 0.178(4) 1 d PD A 2 H1P H 0.7856 1.0284 0.4781 0.093 Uiso 0.178(4) 1 calc PR A 2 C2P C 1.006(2) 0.9451(8) 0.4452(6) 0.076(5) Uiso 0.178(4) 1 d PD A 2 H2P H 1.1231 0.9802 0.4578 0.091 Uiso 0.178(4) 1 calc PR A 2 C3P C 1.063(4) 0.8665(14) 0.4687(16) 0.17(2) Uiso 0.178(4) 1 d PD A 2 H3P H 1.1943 0.8458 0.4540 0.198 Uiso 0.178(4) 1 calc PR A 2 C4P C 0.936(3) 0.8249(9) 0.5091(10) 0.101(6) Uiso 0.178(4) 1 d PD A 2 H4P H 0.9615 0.7730 0.5111 0.121 Uiso 0.178(4) 1 calc PR A 2 C5P C 0.756(4) 0.8566(11) 0.5514(13) 0.122(7) Uiso 0.178(4) 1 d PDU A 2 H5P1 H 0.7813 0.8433 0.5991 0.146 Uiso 0.178(4) 1 calc PR A 2 H5P2 H 0.6197 0.8329 0.5374 0.146 Uiso 0.178(4) 1 calc PR A 2 C6P C 0.730(5) 0.9412(12) 0.5464(9) 0.106(9) Uiso 0.178(4) 1 d PDU A 2 H6P1 H 0.8228 0.9649 0.5806 0.127 Uiso 0.178(4) 1 calc PR A 2 H6P2 H 0.5796 0.9543 0.5572 0.127 Uiso 0.178(4) 1 calc PR A 2 C7P C 0.629(2) 0.9462(17) 0.4219(8) 0.104(11) Uiso 0.178(4) 1 d PD A 2 H7P H 0.4803 0.9360 0.4271 0.125 Uiso 0.178(4) 1 calc PR A 2 C8P C 0.747(2) 0.9404(12) 0.3651(6) 0.062(6) Uiso 0.178(4) 1 d PD A 2 C9P C 0.658(2) 0.9170(9) 0.2953(7) 0.052(9) Uiso 0.178(4) 1 d PD A 2 C10P C 0.763(3) 0.9378(14) 0.2344(8) 0.049(8) Uiso 0.178(4) 1 d PD A 2 H10P H 0.8883 0.9678 0.2358 0.059 Uiso 0.178(4) 1 calc PR A 2 C11P C 0.680(3) 0.9132(11) 0.1720(8) 0.035(5) Uiso 0.178(4) 1 d PD A 2 H11P H 0.7516 0.9253 0.1312 0.042 Uiso 0.178(4) 1 calc PR A 2 C12P C 0.490(5) 0.870(3) 0.1704(8) 0.040(12) Uiso 0.178(4) 1 d PD A 2 C13P C 0.380(3) 0.8534(13) 0.2312(8) 0.042(6) Uiso 0.178(4) 1 d PD A 2 H13P H 0.2494 0.8266 0.2297 0.050 Uiso 0.178(4) 1 calc PR A 2 C14P C 0.464(3) 0.8762(12) 0.2938(8) 0.057(7) Uiso 0.178(4) 1 d PD A 2 H14P H 0.3919 0.8643 0.3344 0.069 Uiso 0.178(4) 1 calc PR A 2 C15P C 0.391(3) 0.846(2) 0.1021(9) 0.058(12) Uiso 0.178(4) 1 d PD A 2 C16P C 0.817(3) 0.6514(11) 0.1045(8) 0.029(4) Uiso 0.178(4) 1 d PD A 2 H16P H 0.9425 0.6167 0.1041 0.035 Uiso 0.178(4) 1 calc PR A 2 C17P C 0.773(4) 0.6772(17) 0.1789(8) 0.056(9) Uiso 0.178(4) 1 d PD A 2 H17P H 0.6821 0.7228 0.1748 0.067 Uiso 0.178(4) 1 calc PR A 2 C18P C 0.978(3) 0.7024(12) 0.2162(8) 0.047(5) Uiso 0.178(4) 1 d PD A 2 H18C H 1.0419 0.7447 0.1913 0.057 Uiso 0.178(4) 1 calc PR A 2 H18D H 1.0830 0.6612 0.2154 0.057 Uiso 0.178(4) 1 calc PR A 2 C19P C 0.942(3) 0.7267(11) 0.2916(9) 0.066(6) Uiso 0.178(4) 1 d PD A 2 H19C H 1.0797 0.7405 0.3129 0.080 Uiso 0.178(4) 1 calc PR A 2 H19D H 0.8438 0.7698 0.2940 0.080 Uiso 0.178(4) 1 calc PR A 2 C20P C 0.842(4) 0.6585(14) 0.3278(11) 0.090(8) Uiso 0.178(4) 1 d PD A 2 H20C H 0.9370 0.6148 0.3228 0.108 Uiso 0.178(4) 1 calc PR A 2 H20D H 0.8256 0.6691 0.3765 0.108 Uiso 0.178(4) 1 calc PR A 2 C21P C 0.621(4) 0.6420(19) 0.2962(11) 0.114(12) Uiso 0.178(4) 1 d PD A 2 H21C H 0.5277 0.6861 0.3013 0.136 Uiso 0.178(4) 1 calc PR A 2 H21D H 0.5528 0.6003 0.3208 0.136 Uiso 0.178(4) 1 calc PR A 2 C22P C 0.637(6) 0.621(2) 0.2199(11) 0.120(18) Uiso 0.178(4) 1 d PD A 2 H22C H 0.7019 0.5715 0.2157 0.144 Uiso 0.178(4) 1 calc PR A 2 H22D H 0.4914 0.6193 0.2005 0.144 Uiso 0.178(4) 1 calc PR A 2 C23P C 0.626(3) 0.6148(10) 0.0670(10) 0.054(6) Uiso 0.178(4) 1 d PD A 2 H23D H 0.6686 0.6025 0.0208 0.081 Uiso 0.178(4) 1 calc PR A 2 H23E H 0.5047 0.6494 0.0659 0.081 Uiso 0.178(4) 1 calc PR A 2 H23F H 0.5832 0.5693 0.0906 0.081 Uiso 0.178(4) 1 calc PR A 2 O1P O 0.9712(16) 0.9470(7) 0.3702(5) 0.084(4) Uiso 0.178(4) 1 d PDU A 2 O2P O 0.203(3) 0.8185(14) 0.1051(14) 0.066(9) Uiso 0.178(4) 1 d PD A 2 O3P O 0.520(3) 0.8380(16) 0.0518(11) 0.041(4) Uiso 0.178(4) 1 d PD A 2 N1P N 0.873(4) 0.7217(13) 0.0629(13) 0.028(5) Uiso 0.178(4) 1 d PDU A 2 H1P1 H 0.9669 0.7503 0.0864 0.041 Uiso 0.178(4) 1 calc PR A 2 H1P2 H 0.7516 0.7481 0.0548 0.041 Uiso 0.178(4) 1 calc PR A 2 H1P3 H 0.9331 0.7080 0.0231 0.041 Uiso 0.178(4) 1 calc PR A 2 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 C1R 0.078(2) 0.062(2) 0.059(2) -0.0110(14) -0.019(2) -0.0001(16) C2R 0.0672(19) 0.112(3) 0.084(3) 0.003(2) -0.0159(18) 0.0038(19) C3R 0.093(3) 0.102(4) 0.085(3) -0.003(2) 0.000(2) 0.033(3) C4R 0.106(2) 0.0594(18) 0.0602(18) -0.0043(13) -0.0029(16) 0.0010(17) C5R 0.126(3) 0.090(2) 0.0530(19) 0.0118(17) 0.000(2) -0.016(2) C6R 0.103(3) 0.109(3) 0.0446(18) -0.0095(16) -0.0119(17) 0.004(2) C7R 0.065(2) 0.0612(19) 0.0454(17) -0.0116(12) -0.0037(13) -0.0055(17) C8R 0.079(2) 0.056(2) 0.0563(19) -0.0027(15) -0.0047(16) -0.009(2) C9R 0.0567(18) 0.0455(17) 0.048(2) -0.0061(11) -0.0053(13) -0.0056(16) C10R 0.0460(18) 0.062(2) 0.057(2) -0.0101(14) -0.0035(14) -0.004(2) C11R 0.0519(19) 0.051(2) 0.049(2) -0.0023(13) 0.0014(13) 0.0003(19) C12R 0.051(4) 0.047(3) 0.052(4) -0.0053(12) -0.0022(12) 0.0000(16) C13R 0.0532(19) 0.063(3) 0.063(2) -0.0179(17) 0.0103(13) -0.0167(19) C14R 0.071(3) 0.054(2) 0.0503(19) -0.0130(14) 0.0131(14) -0.0122(18) C15R 0.058(2) 0.050(2) 0.045(2) -0.0037(15) -0.0114(15) 0.0036(18) C16R 0.060(3) 0.054(2) 0.052(2) 0.0033(12) 0.0027(17) 0.005(2) C17R 0.057(2) 0.053(2) 0.046(2) 0.0057(11) 0.0060(13) 0.0017(18) C18R 0.085(3) 0.092(3) 0.0469(19) 0.0034(16) -0.0007(16) -0.030(2) C19R 0.116(3) 0.097(3) 0.0422(18) -0.0003(19) -0.0057(19) -0.024(3) C20R 0.104(4) 0.132(4) 0.0446(19) 0.023(2) 0.005(2) -0.008(3) C21R 0.107(3) 0.159(5) 0.058(2) 0.022(3) 0.021(2) -0.033(4) C22R 0.080(3) 0.085(3) 0.059(2) 0.0193(17) 0.0112(16) -0.018(2) C23R 0.084(3) 0.066(2) 0.071(2) 0.0060(19) -0.015(2) -0.023(2) O1R 0.139(2) 0.116(2) 0.0676(14) -0.0065(14) -0.0097(14) -0.0828(19) O2R 0.064(2) 0.134(5) 0.070(3) -0.0222(16) -0.0104(12) -0.0374(19) O3R 0.072(2) 0.078(3) 0.0449(16) -0.0092(15) -0.0135(13) 0.0119(17) N1R 0.054(2) 0.073(3) 0.041(2) -0.0076(13) 0.0004(12) -0.0046(11) _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 C1R C2R 1.492(5) . ? C1R C7R 1.545(5) . ? C1R C6R 1.567(5) . ? C2R C3R 1.320(6) . ? C3R C4R 1.517(6) . ? C4R C5R 1.544(4) . ? C4R C7R 1.553(5) . ? C5R C6R 1.524(6) . ? C7R C8R 1.490(4) . ? C8R O1R 1.212(5) . ? C8R C9R 1.496(4) . ? C9R C10R 1.380(5) . ? C9R C14R 1.393(5) . ? C10R C11R 1.370(4) . ? C11R C12R 1.384(5) . ? C12R C13R 1.374(4) . ? C12R C15R 1.511(4) . ? C13R C14R 1.375(4) . ? C15R O2R 1.238(4) . ? C15R O3R 1.259(4) . ? C16R N1R 1.491(4) . ? C16R C23R 1.507(5) . ? C16R C17R 1.515(4) . ? C17R C18R 1.507(6) . ? C17R C22R 1.512(5) . ? C18R C19R 1.520(4) . ? C19R C20R 1.502(6) . ? C20R C21R 1.494(6) . ? C21R C22R 1.517(5) . ? C1P C7P 1.506(10) . ? C1P C6P 1.514(10) . ? C1P C2P 1.549(9) . ? C2P O1P 1.474(9) . ? C2P C3P 1.500(10) . ? C3P C4P 1.325(10) . ? C4P C5P 1.484(10) . ? C5P C6P 1.504(10) . ? C7P C8P 1.325(9) . ? C8P O1P 1.377(9) . ? C8P C9P 1.521(8) . ? C9P C14P 1.386(9) . ? C9P C10P 1.397(9) . ? C10P C11P 1.387(9) . ? C11P C12P 1.389(9) . ? C12P C13P 1.390(9) . ? C12P C15P 1.522(9) . ? C13P C14P 1.380(9) . ? C15P O2P 1.245(10) . ? C15P O3P 1.268(10) . ? C16P N1P 1.520(10) . ? C16P C23P 1.525(10) . ? C16P C17P 1.540(10) . ? C17P C22P 1.513(10) . ? C17P C18P 1.517(10) . ? C18P C19P 1.544(10) . ? C19P C20P 1.522(10) . ? C20P C21P 1.515(10) . ? C21P C22P 1.530(10) . ? 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 C2R C1R C7R 102.5(3) . . ? C2R C1R C6R 104.3(4) . . ? C7R C1R C6R 99.3(3) . . ? C3R C2R C1R 108.1(4) . . ? C2R C3R C4R 107.4(3) . . ? C3R C4R C5R 104.6(3) . . ? C3R C4R C7R 101.2(3) . . ? C5R C4R C7R 99.9(3) . . ? C6R C5R C4R 103.7(3) . . ? C5R C6R C1R 102.8(3) . . ? C8R C7R C1R 114.8(3) . . ? C8R C7R C4R 115.2(3) . . ? C1R C7R C4R 92.5(3) . . ? O1R C8R C7R 121.6(3) . . ? O1R C8R C9R 118.8(3) . . ? C7R C8R C9R 119.6(4) . . ? C10R C9R C14R 118.2(3) . . ? C10R C9R C8R 119.0(4) . . ? C14R C9R C8R 122.8(3) . . ? C11R C10R C9R 121.4(4) . . ? C10R C11R C12R 120.2(4) . . ? C13R C12R C11R 118.8(4) . . ? C13R C12R C15R 121.0(4) . . ? C11R C12R C15R 120.2(4) . . ? C12R C13R C14R 121.2(4) . . ? C13R C14R C9R 120.1(3) . . ? O2R C15R O3R 125.0(4) . . ? O2R C15R C12R 117.7(4) . . ? O3R C15R C12R 117.3(4) . . ? N1R C16R C23R 108.0(4) . . ? N1R C16R C17R 111.1(4) . . ? C23R C16R C17R 114.8(4) . . ? C18R C17R C22R 108.3(4) . . ? C18R C17R C16R 112.9(4) . . ? C22R C17R C16R 111.6(4) . . ? C17R C18R C19R 112.3(4) . . ? C20R C19R C18R 111.0(4) . . ? C21R C20R C19R 110.7(3) . . ? C20R C21R C22R 111.9(4) . . ? C17R C22R C21R 111.9(5) . . ? C7P C1P C6P 111.7(13) . . ? C7P C1P C2P 100.5(9) . . ? C6P C1P C2P 115.6(12) . . ? O1P C2P C3P 110.8(13) . . ? O1P C2P C1P 104.7(8) . . ? C3P C2P C1P 112.0(10) . . ? C4P C3P C2P 123.8(12) . . ? C3P C4P C5P 123.6(12) . . ? C4P C5P C6P 114.6(11) . . ? C5P C6P C1P 113.6(12) . . ? C8P C7P C1P 104.9(9) . . ? C7P C8P O1P 118.6(9) . . ? C7P C8P C9P 124.6(10) . . ? O1P C8P C9P 116.4(9) . . ? C14P C9P C10P 120.9(10) . . ? C14P C9P C8P 117.9(10) . . ? C10P C9P C8P 121.2(10) . . ? C11P C10P C9P 119.3(11) . . ? C10P C11P C12P 119.8(11) . . ? C11P C12P C13P 120.1(10) . . ? C11P C12P C15P 120.5(11) . . ? C13P C12P C15P 119.3(11) . . ? C14P C13P C12P 120.5(11) . . ? C13P C14P C9P 119.2(11) . . ? O2P C15P O3P 124.8(16) . . ? O2P C15P C12P 115.8(13) . . ? O3P C15P C12P 117.1(14) . . ? N1P C16P C23P 105.3(12) . . ? N1P C16P C17P 107.3(13) . . ? C23P C16P C17P 116.0(12) . . ? C22P C17P C18P 113.0(13) . . ? C22P C17P C16P 113.6(13) . . ? C18P C17P C16P 112.9(13) . . ? C17P C18P C19P 114.6(11) . . ? C20P C19P C18P 106.2(12) . . ? C21P C20P C19P 108.8(13) . . ? C20P C21P C22P 112.3(14) . . ? C17P C22P C21P 113.2(13) . . ? C8P O1P C2P 102.2(8) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.201 _refine_diff_density_min -0.132 _refine_diff_density_rms 0.039 #===END data_20.6%P _database_code_depnum_ccdc_archive 'CCDC 608919' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1363(8) _cell_length_b 17.631(2) _cell_length_c 19.450(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2104.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.166 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9593 _exptl_absorpt_correction_T_max 0.9775 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11311 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3673 _reflns_number_gt 2508 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.1080P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.018(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3673 _refine_ls_number_parameters 354 _refine_ls_number_restraints 177 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0546 _refine_ls_wR_factor_ref 0.1615 _refine_ls_wR_factor_gt 0.1446 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.985 _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 C1R C 0.8334(10) 0.9751(3) 0.4851(2) 0.0741(19) Uani 0.794(5) 1 d PD A 1 H1R H 0.8364 1.0307 0.4853 0.089 Uiso 0.794(5) 1 calc PR A 1 C2R C 1.0496(7) 0.9365(3) 0.4846(3) 0.0976(16) Uani 0.794(5) 1 d PD A 1 H2R H 1.1813 0.9579 0.4982 0.117 Uiso 0.794(5) 1 calc PR A 1 C3R C 1.0214(11) 0.8666(4) 0.4614(3) 0.101(3) Uani 0.794(5) 1 d PD A 1 H3R H 1.1297 0.8305 0.4543 0.121 Uiso 0.794(5) 1 calc PR A 1 C4R C 0.7781(7) 0.8563(2) 0.4484(2) 0.0853(14) Uani 0.794(5) 1 d PD A 1 H4R H 0.7369 0.8145 0.4178 0.102 Uiso 0.794(5) 1 calc PR A 1 C5R C 0.6774(10) 0.8551(3) 0.5213(2) 0.1006(16) Uani 0.794(5) 1 d PDU A 1 H5R1 H 0.5236 0.8425 0.5196 0.121 Uiso 0.794(5) 1 calc PR A 1 H5R2 H 0.7516 0.8189 0.5507 0.121 Uiso 0.794(5) 1 calc PR A 1 C6R C 0.7121(14) 0.9366(4) 0.5470(2) 0.099(2) Uani 0.794(5) 1 d PDU A 1 H6R1 H 0.8008 0.9374 0.5883 0.119 Uiso 0.794(5) 1 calc PR A 1 H6R2 H 0.5741 0.9614 0.5563 0.119 Uiso 0.794(5) 1 calc PR A 1 C7R C 0.7096(10) 0.9377(3) 0.42495(17) 0.0656(11) Uani 0.794(5) 1 d PD A 1 H7R H 0.5519 0.9453 0.4288 0.079 Uiso 0.794(5) 1 calc PR A 1 C8R C 0.7921(8) 0.9600(3) 0.3558(2) 0.0728(14) Uani 0.794(5) 1 d PD A 1 C9R C 0.6882(9) 0.9271(3) 0.2928(2) 0.0571(18) Uani 0.794(5) 1 d PD A 1 C10R C 0.8044(11) 0.9265(4) 0.2319(3) 0.064(2) Uani 0.794(5) 1 d PD A 1 H10R H 0.9447 0.9464 0.2311 0.077 Uiso 0.794(5) 1 calc PR A 1 C11R C 0.7166(12) 0.8970(4) 0.1726(3) 0.060(2) Uani 0.794(5) 1 d PD A 1 H11R H 0.7993 0.8958 0.1325 0.072 Uiso 0.794(5) 1 calc PR A 1 C12R C 0.5048(13) 0.8691(7) 0.1722(3) 0.054(2) Uani 0.794(5) 1 d PDU A 1 C13R C 0.3866(9) 0.8703(4) 0.2321(2) 0.0620(17) Uani 0.794(5) 1 d PD A 1 H13R H 0.2437 0.8527 0.2321 0.074 Uiso 0.794(5) 1 calc PR A 1 C14R C 0.4771(8) 0.8973(4) 0.2923(2) 0.0642(15) Uani 0.794(5) 1 d PD A 1 H14R H 0.3969 0.8956 0.3328 0.077 Uiso 0.794(5) 1 calc PR A 1 C15R C 0.4114(9) 0.8344(5) 0.1080(3) 0.056(2) Uani 0.794(5) 1 d PD A 1 C16R C 0.7714(12) 0.6571(5) 0.1028(3) 0.064(2) Uani 0.794(5) 1 d PD A 1 H16R H 0.8757 0.6152 0.0996 0.077 Uiso 0.794(5) 1 calc PR A 1 C17R C 0.7319(12) 0.6723(4) 0.1783(2) 0.0573(17) Uani 0.794(5) 1 d PD A 1 H17R H 0.6393 0.7175 0.1819 0.069 Uiso 0.794(5) 1 calc PR A 1 C18R C 0.9409(11) 0.6880(4) 0.2176(2) 0.0804(19) Uani 0.794(5) 1 d PD A 1 H18A H 1.0156 0.7305 0.1965 0.097 Uiso 0.794(5) 1 calc PR A 1 H18B H 1.0355 0.6440 0.2143 0.097 Uiso 0.794(5) 1 calc PR A 1 C19R C 0.8995(12) 0.7057(4) 0.2933(2) 0.0897(17) Uani 0.794(5) 1 d PD A 1 H19A H 1.0374 0.7130 0.3167 0.108 Uiso 0.794(5) 1 calc PR A 1 H19B H 0.8160 0.7522 0.2972 0.108 Uiso 0.794(5) 1 calc PR A 1 C20R C 0.7758(11) 0.6413(4) 0.3267(2) 0.0990(18) Uani 0.794(5) 1 d PD A 1 H20A H 0.8674 0.5965 0.3280 0.119 Uiso 0.794(5) 1 calc PR A 1 H20B H 0.7401 0.6549 0.3737 0.119 Uiso 0.794(5) 1 calc PR A 1 C21R C 0.5708(12) 0.6236(6) 0.2884(3) 0.118(2) Uani 0.794(5) 1 d PD A 1 H21A H 0.4713 0.6662 0.2923 0.141 Uiso 0.794(5) 1 calc PR A 1 H21B H 0.5013 0.5798 0.3090 0.141 Uiso 0.794(5) 1 calc PR A 1 C22R C 0.6150(13) 0.6077(5) 0.2128(3) 0.082(2) Uani 0.794(5) 1 d PD A 1 H22A H 0.7025 0.5621 0.2088 0.098 Uiso 0.794(5) 1 calc PR A 1 H22B H 0.4778 0.5987 0.1894 0.098 Uiso 0.794(5) 1 calc PR A 1 C23R C 0.5708(12) 0.6345(4) 0.0626(3) 0.0824(18) Uani 0.794(5) 1 d PD A 1 H23A H 0.6114 0.6226 0.0162 0.124 Uiso 0.794(5) 1 calc PR A 1 H23B H 0.4686 0.6757 0.0625 0.124 Uiso 0.794(5) 1 calc PR A 1 H23C H 0.5051 0.5908 0.0835 0.124 Uiso 0.794(5) 1 calc PR A 1 O1R O 0.9429(7) 1.0040(3) 0.34921(16) 0.1216(17) Uani 0.794(5) 1 d PD A 1 O2R O 0.2165(10) 0.8146(5) 0.1090(3) 0.090(2) Uani 0.794(5) 1 d PDU A 1 O3R O 0.5318(15) 0.8299(8) 0.0560(4) 0.072(3) Uani 0.794(5) 1 d PD A 1 N1R N 0.8715(17) 0.7241(6) 0.0685(4) 0.063(3) Uani 0.794(5) 1 d PDU A 1 H1R1 H 0.8931 0.7138 0.0242 0.095 Uiso 0.794(5) 1 calc PR A 1 H1R2 H 0.9985 0.7347 0.0884 0.095 Uiso 0.794(5) 1 calc PR A 1 H1R3 H 0.7828 0.7638 0.0724 0.095 Uiso 0.794(5) 1 calc PR A 1 C1P C 0.785(3) 0.9726(11) 0.4764(7) 0.076(9) Uiso 0.206(5) 1 d PD A 2 H1P H 0.7823 1.0281 0.4784 0.091 Uiso 0.206(5) 1 calc PR A 2 C2P C 1.004(2) 0.9459(9) 0.4458(6) 0.083(6) Uiso 0.206(5) 1 d PD A 2 H2P H 1.1192 0.9824 0.4573 0.100 Uiso 0.206(5) 1 calc PR A 2 C3P C 1.068(4) 0.8683(14) 0.4704(15) 0.16(2) Uiso 0.206(5) 1 d PD A 2 H3P H 1.2051 0.8495 0.4587 0.193 Uiso 0.206(5) 1 calc PR A 2 C4P C 0.937(3) 0.8256(9) 0.5083(9) 0.096(6) Uiso 0.206(5) 1 d PD A 2 H4P H 0.9536 0.7732 0.5061 0.115 Uiso 0.206(5) 1 calc PR A 2 C5P C 0.765(4) 0.8564(11) 0.5538(13) 0.124(7) Uiso 0.206(5) 1 d PDU A 2 H5P1 H 0.8035 0.8455 0.6011 0.148 Uiso 0.206(5) 1 calc PR A 2 H5P2 H 0.6291 0.8303 0.5440 0.148 Uiso 0.206(5) 1 calc PR A 2 C6P C 0.729(5) 0.9404(12) 0.5465(9) 0.114(9) Uiso 0.206(5) 1 d PDU A 2 H6P1 H 0.8153 0.9664 0.5809 0.137 Uiso 0.206(5) 1 calc PR A 2 H6P2 H 0.5766 0.9513 0.5561 0.137 Uiso 0.206(5) 1 calc PR A 2 C7P C 0.627(2) 0.9455(19) 0.4223(8) 0.107(12) Uiso 0.206(5) 1 d PD A 2 H7P H 0.4793 0.9355 0.4276 0.129 Uiso 0.206(5) 1 calc PR A 2 C8P C 0.746(2) 0.9391(11) 0.3656(7) 0.060(6) Uiso 0.206(5) 1 d PD A 2 C9P C 0.658(2) 0.9157(9) 0.2956(7) 0.058(9) Uiso 0.206(5) 1 d PD A 2 C10P C 0.768(3) 0.9371(14) 0.2359(9) 0.050(8) Uiso 0.206(5) 1 d PD A 2 H10P H 0.8896 0.9683 0.2384 0.060 Uiso 0.206(5) 1 calc PR A 2 C11P C 0.693(4) 0.9118(16) 0.1729(9) 0.041(6) Uiso 0.206(5) 1 d PD A 2 H11P H 0.7741 0.9203 0.1332 0.049 Uiso 0.206(5) 1 calc PR A 2 C12P C 0.495(5) 0.873(3) 0.1697(9) 0.052(9) Uiso 0.206(5) 1 d PDU A 2 C13P C 0.393(4) 0.8501(14) 0.2297(9) 0.064(9) Uiso 0.206(5) 1 d PD A 2 H13P H 0.2738 0.8174 0.2272 0.077 Uiso 0.206(5) 1 calc PR A 2 C14P C 0.465(3) 0.8750(13) 0.2932(9) 0.072(9) Uiso 0.206(5) 1 d PD A 2 H14P H 0.3864 0.8648 0.3330 0.087 Uiso 0.206(5) 1 calc PR A 2 C15P C 0.410(4) 0.8486(18) 0.0998(9) 0.057(11) Uiso 0.206(5) 1 d PD A 2 C16P C 0.814(4) 0.6528(13) 0.1046(9) 0.035(5) Uiso 0.206(5) 1 d PD A 2 H16P H 0.9351 0.6166 0.1041 0.042 Uiso 0.206(5) 1 calc PR A 2 C17P C 0.774(4) 0.6782(18) 0.1791(9) 0.063(9) Uiso 0.206(5) 1 d PD A 2 H17P H 0.6813 0.7233 0.1767 0.076 Uiso 0.206(5) 1 calc PR A 2 C18P C 0.984(3) 0.7027(14) 0.2146(9) 0.059(6) Uiso 0.206(5) 1 d PD A 2 H18C H 1.0466 0.7451 0.1896 0.071 Uiso 0.206(5) 1 calc PR A 2 H18D H 1.0880 0.6612 0.2129 0.071 Uiso 0.206(5) 1 calc PR A 2 C19P C 0.950(4) 0.7261(15) 0.2902(10) 0.098(10) Uiso 0.206(5) 1 d PD A 2 H19C H 1.0877 0.7398 0.3110 0.117 Uiso 0.206(5) 1 calc PR A 2 H19D H 0.8530 0.7696 0.2926 0.117 Uiso 0.206(5) 1 calc PR A 2 C20P C 0.850(4) 0.6592(17) 0.3280(11) 0.105(10) Uiso 0.206(5) 1 d PD A 2 H20C H 0.9470 0.6159 0.3252 0.126 Uiso 0.206(5) 1 calc PR A 2 H20D H 0.8305 0.6720 0.3761 0.126 Uiso 0.206(5) 1 calc PR A 2 C21P C 0.632(4) 0.639(2) 0.2965(12) 0.113(12) Uiso 0.206(5) 1 d PD A 2 H21C H 0.5325 0.6814 0.3021 0.135 Uiso 0.206(5) 1 calc PR A 2 H21D H 0.5706 0.5959 0.3209 0.135 Uiso 0.206(5) 1 calc PR A 2 C22P C 0.650(6) 0.620(2) 0.2202(12) 0.114(17) Uiso 0.206(5) 1 d PD A 2 H22C H 0.7215 0.5708 0.2155 0.137 Uiso 0.206(5) 1 calc PR A 2 H22D H 0.5041 0.6147 0.2012 0.137 Uiso 0.206(5) 1 calc PR A 2 C23P C 0.619(4) 0.6163(13) 0.0687(13) 0.068(8) Uiso 0.206(5) 1 d PD A 2 H23D H 0.6583 0.6035 0.0223 0.101 Uiso 0.206(5) 1 calc PR A 2 H23E H 0.4994 0.6513 0.0682 0.101 Uiso 0.206(5) 1 calc PR A 2 H23F H 0.5774 0.5712 0.0930 0.101 Uiso 0.206(5) 1 calc PR A 2 O1P O 0.9694(17) 0.9451(8) 0.3704(5) 0.085(4) Uiso 0.206(5) 1 d PD A 2 O2P O 0.217(4) 0.8270(18) 0.0972(14) 0.075(7) Uiso 0.206(5) 1 d PDU A 2 O3P O 0.554(5) 0.832(3) 0.0548(15) 0.055(8) Uiso 0.206(5) 1 d PD A 2 N1P N 0.877(5) 0.7208(15) 0.0617(14) 0.034(6) Uiso 0.206(5) 1 d PDU A 2 H1P1 H 0.9706 0.7494 0.0851 0.051 Uiso 0.206(5) 1 calc PR A 2 H1P2 H 0.7583 0.7479 0.0520 0.051 Uiso 0.206(5) 1 calc PR A 2 H1P3 H 0.9387 0.7053 0.0228 0.051 Uiso 0.206(5) 1 calc PR A 2 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 C1R 0.086(3) 0.069(3) 0.068(3) -0.011(2) -0.023(3) 0.001(2) C2R 0.078(3) 0.119(5) 0.096(4) 0.004(3) -0.013(3) 0.003(3) C3R 0.100(4) 0.113(5) 0.089(4) -0.003(3) 0.003(3) 0.029(4) C4R 0.122(4) 0.069(3) 0.064(2) -0.0050(19) -0.002(2) -0.003(2) C5R 0.144(4) 0.096(3) 0.061(3) 0.011(2) 0.001(3) -0.019(3) C6R 0.125(5) 0.123(5) 0.050(2) -0.010(2) -0.013(3) 0.004(3) C7R 0.081(3) 0.067(3) 0.049(2) -0.0128(17) -0.002(2) -0.008(3) C8R 0.089(3) 0.065(3) 0.065(3) 0.000(2) -0.006(2) -0.009(3) C9R 0.066(3) 0.050(2) 0.056(3) -0.0063(16) -0.0068(18) -0.007(2) C10R 0.054(3) 0.073(4) 0.065(3) -0.015(2) -0.004(2) -0.003(3) C11R 0.068(3) 0.055(4) 0.058(3) -0.006(2) 0.0023(19) -0.004(3) C12R 0.054(3) 0.048(3) 0.060(3) -0.0043(17) -0.0017(16) 0.0014(19) C13R 0.057(2) 0.068(4) 0.061(3) -0.024(2) 0.0116(17) -0.013(2) C14R 0.080(4) 0.059(3) 0.054(3) -0.0139(19) 0.0184(19) -0.012(2) C15R 0.070(4) 0.053(3) 0.046(2) -0.001(3) -0.0107(18) 0.001(2) C16R 0.072(4) 0.061(3) 0.060(3) 0.0051(17) 0.003(2) 0.002(3) C17R 0.064(3) 0.058(3) 0.051(3) 0.0051(15) 0.0043(18) 0.002(2) C18R 0.093(4) 0.100(4) 0.048(2) 0.006(2) 0.000(2) -0.036(3) C19R 0.123(5) 0.105(4) 0.041(2) 0.002(2) -0.004(2) -0.024(4) C20R 0.107(5) 0.139(5) 0.051(3) 0.027(3) 0.004(3) -0.010(4) C21R 0.117(5) 0.175(7) 0.061(3) 0.025(4) 0.021(3) -0.035(5) C22R 0.085(4) 0.092(4) 0.068(3) 0.020(2) 0.007(2) -0.024(3) C23R 0.099(4) 0.074(3) 0.075(3) 0.008(3) -0.021(3) -0.028(3) O1R 0.157(3) 0.132(3) 0.076(2) -0.013(2) -0.007(2) -0.085(3) O2R 0.074(2) 0.131(5) 0.066(3) -0.012(3) -0.0129(19) -0.039(2) O3R 0.073(4) 0.092(4) 0.052(3) -0.0128(16) -0.0115(17) 0.005(3) N1R 0.064(3) 0.081(4) 0.045(3) -0.010(2) -0.0002(18) -0.0069(17) _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 C1R C2R 1.491(6) . ? C1R C7R 1.543(6) . ? C1R C6R 1.570(6) . ? C2R C3R 1.325(7) . ? C3R C4R 1.525(7) . ? C4R C5R 1.548(5) . ? C4R C7R 1.564(6) . ? C5R C6R 1.535(7) . ? C7R C8R 1.489(5) . ? C8R O1R 1.215(6) . ? C8R C9R 1.499(5) . ? C9R C10R 1.382(6) . ? C9R C14R 1.398(6) . ? C10R C11R 1.376(5) . ? C11R C12R 1.390(5) . ? C12R C13R 1.371(5) . ? C12R C15R 1.505(5) . ? C13R C14R 1.381(5) . ? C15R O2R 1.246(5) . ? C15R O3R 1.254(5) . ? C16R N1R 1.489(5) . ? C16R C23R 1.512(6) . ? C16R C17R 1.512(5) . ? C17R C22R 1.505(6) . ? C17R C18R 1.518(6) . ? C18R C19R 1.526(5) . ? C19R C20R 1.513(7) . ? C20R C21R 1.494(7) . ? C21R C22R 1.522(6) . ? C1P C7P 1.507(10) . ? C1P C6P 1.516(9) . ? C1P C2P 1.546(9) . ? C2P O1P 1.481(9) . ? C2P C3P 1.502(9) . ? C3P C4P 1.327(10) . ? C4P C5P 1.481(10) . ? C5P C6P 1.506(10) . ? C7P C8P 1.327(9) . ? C8P O1P 1.378(9) . ? C8P C9P 1.520(8) . ? C9P C14P 1.388(9) . ? C9P C10P 1.393(9) . ? C10P C11P 1.382(9) . ? C11P C12P 1.393(9) . ? C12P C13P 1.387(9) . ? C12P C15P 1.520(9) . ? C13P C14P 1.384(9) . ? C15P O2P 1.248(10) . ? C15P O3P 1.272(10) . ? C16P N1P 1.511(10) . ? C16P C23P 1.525(10) . ? C16P C17P 1.537(10) . ? C17P C22P 1.515(10) . ? C17P C18P 1.524(10) . ? C18P C19P 1.542(10) . ? C19P C20P 1.518(10) . ? C20P C21P 1.515(10) . ? C21P C22P 1.528(10) . ? 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 C2R C1R C7R 103.8(4) . . ? C2R C1R C6R 103.3(4) . . ? C7R C1R C6R 99.4(4) . . ? C3R C2R C1R 108.1(5) . . ? C2R C3R C4R 107.2(5) . . ? C3R C4R C5R 103.9(4) . . ? C3R C4R C7R 101.6(4) . . ? C5R C4R C7R 99.9(3) . . ? C6R C5R C4R 103.3(3) . . ? C5R C6R C1R 102.8(4) . . ? C8R C7R C1R 113.9(4) . . ? C8R C7R C4R 114.5(4) . . ? C1R C7R C4R 92.2(3) . . ? O1R C8R C7R 121.6(4) . . ? O1R C8R C9R 119.0(4) . . ? C7R C8R C9R 119.4(5) . . ? C10R C9R C14R 117.9(4) . . ? C10R C9R C8R 119.0(5) . . ? C14R C9R C8R 123.1(4) . . ? C11R C10R C9R 121.3(5) . . ? C10R C11R C12R 120.2(5) . . ? C13R C12R C11R 119.0(4) . . ? C13R C12R C15R 120.6(4) . . ? C11R C12R C15R 120.3(4) . . ? C12R C13R C14R 120.8(4) . . ? C13R C14R C9R 120.6(4) . . ? O2R C15R O3R 124.0(5) . . ? O2R C15R C12R 117.8(4) . . ? O3R C15R C12R 118.1(5) . . ? N1R C16R C23R 108.2(5) . . ? N1R C16R C17R 111.1(5) . . ? C23R C16R C17R 114.8(5) . . ? C22R C17R C16R 112.0(4) . . ? C22R C17R C18R 108.4(5) . . ? C16R C17R C18R 112.7(5) . . ? C17R C18R C19R 112.5(5) . . ? C20R C19R C18R 110.1(5) . . ? C21R C20R C19R 111.4(4) . . ? C20R C21R C22R 111.7(5) . . ? C17R C22R C21R 112.1(6) . . ? C7P C1P C6P 111.2(13) . . ? C7P C1P C2P 101.2(9) . . ? C6P C1P C2P 115.6(12) . . ? O1P C2P C3P 110.1(13) . . ? O1P C2P C1P 104.9(8) . . ? C3P C2P C1P 112.4(10) . . ? C4P C3P C2P 122.3(13) . . ? C3P C4P C5P 123.9(13) . . ? C4P C5P C6P 114.2(11) . . ? C5P C6P C1P 114.8(12) . . ? C8P C7P C1P 104.7(9) . . ? C7P C8P O1P 118.9(9) . . ? C7P C8P C9P 125.0(10) . . ? O1P C8P C9P 115.7(9) . . ? C14P C9P C10P 121.5(10) . . ? C14P C9P C8P 118.3(10) . . ? C10P C9P C8P 120.2(11) . . ? C11P C10P C9P 119.5(12) . . ? C10P C11P C12P 119.0(12) . . ? C13P C12P C11P 120.1(11) . . ? C13P C12P C15P 120.9(12) . . ? C11P C12P C15P 118.5(11) . . ? C14P C13P C12P 120.7(12) . . ? C13P C14P C9P 118.0(11) . . ? O2P C15P O3P 124.1(17) . . ? O2P C15P C12P 116.7(13) . . ? O3P C15P C12P 116.3(15) . . ? N1P C16P C23P 106.4(13) . . ? N1P C16P C17P 109.2(13) . . ? C23P C16P C17P 115.6(13) . . ? C22P C17P C18P 112.5(13) . . ? C22P C17P C16P 112.2(13) . . ? C18P C17P C16P 112.1(13) . . ? C17P C18P C19P 113.0(12) . . ? C20P C19P C18P 108.1(13) . . ? C21P C20P C19P 110.1(13) . . ? C20P C21P C22P 112.4(14) . . ? C17P C22P C21P 113.3(14) . . ? C8P O1P C2P 102.3(8) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.222 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.042 #===END data_23.4%P _database_code_depnum_ccdc_archive 'CCDC 608920' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1416(10) _cell_length_b 17.622(3) _cell_length_c 19.468(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2107.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.165 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9593 _exptl_absorpt_correction_T_max 0.9775 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11353 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.35 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3682 _reflns_number_gt 2406 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.1304P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3682 _refine_ls_number_parameters 354 _refine_ls_number_restraints 195 _refine_ls_R_factor_all 0.0908 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1967 _refine_ls_wR_factor_gt 0.1743 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.013 _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 C1R C 0.8344(11) 0.9753(3) 0.4846(3) 0.078(2) Uani 0.766(6) 1 d PD A 1 H1R H 0.8370 1.0309 0.4845 0.093 Uiso 0.766(6) 1 calc PR A 1 C2R C 1.0508(9) 0.9371(4) 0.4842(4) 0.103(2) Uani 0.766(6) 1 d PD A 1 H2R H 1.1825 0.9585 0.4976 0.123 Uiso 0.766(6) 1 calc PR A 1 C3R C 1.0215(11) 0.8668(5) 0.4612(4) 0.109(3) Uani 0.766(6) 1 d PDU A 1 H3R H 1.1295 0.8307 0.4541 0.130 Uiso 0.766(6) 1 calc PR A 1 C4R C 0.7794(9) 0.8563(3) 0.4485(2) 0.0906(18) Uani 0.766(6) 1 d PD A 1 H4R H 0.7380 0.8145 0.4180 0.109 Uiso 0.766(6) 1 calc PR A 1 C5R C 0.6798(13) 0.8551(3) 0.5217(3) 0.104(2) Uani 0.766(6) 1 d PDU A 1 H5R1 H 0.5261 0.8425 0.5204 0.125 Uiso 0.766(6) 1 calc PR A 1 H5R2 H 0.7546 0.8189 0.5509 0.125 Uiso 0.766(6) 1 calc PR A 1 C6R C 0.7155(17) 0.9371(4) 0.5471(3) 0.104(3) Uani 0.766(6) 1 d PDU A 1 H6R1 H 0.8056 0.9382 0.5880 0.124 Uiso 0.766(6) 1 calc PR A 1 H6R2 H 0.5780 0.9620 0.5568 0.124 Uiso 0.766(6) 1 calc PR A 1 C7R C 0.7107(11) 0.9377(3) 0.4251(2) 0.0714(14) Uani 0.766(6) 1 d PDU A 1 H7R H 0.5531 0.9453 0.4292 0.086 Uiso 0.766(6) 1 calc PR A 1 C8R C 0.7920(10) 0.9599(4) 0.3558(3) 0.0790(18) Uani 0.766(6) 1 d PD A 1 C9R C 0.6870(11) 0.9266(4) 0.2933(2) 0.058(2) Uani 0.766(6) 1 d PD A 1 C10R C 0.8063(13) 0.9256(5) 0.2327(3) 0.068(3) Uani 0.766(6) 1 d PD A 1 H10R H 0.9462 0.9458 0.2323 0.081 Uiso 0.766(6) 1 calc PR A 1 C11R C 0.7218(12) 0.8956(4) 0.1736(3) 0.064(2) Uani 0.766(6) 1 d PD A 1 H11R H 0.8072 0.8928 0.1342 0.076 Uiso 0.766(6) 1 calc PR A 1 C12R C 0.5079(17) 0.8693(9) 0.1724(4) 0.059(5) Uani 0.766(6) 1 d PD A 1 C13R C 0.3865(9) 0.8701(5) 0.2316(3) 0.0623(19) Uani 0.766(6) 1 d PD A 1 H13R H 0.2434 0.8528 0.2311 0.075 Uiso 0.766(6) 1 calc PR A 1 C14R C 0.4770(9) 0.8966(5) 0.2922(2) 0.0658(18) Uani 0.766(6) 1 d PD A 1 H14R H 0.3967 0.8944 0.3326 0.079 Uiso 0.766(6) 1 calc PR A 1 C15R C 0.4172(14) 0.8350(7) 0.1074(4) 0.060(3) Uani 0.766(6) 1 d PD A 1 C16R C 0.7721(14) 0.6571(5) 0.1022(3) 0.066(2) Uani 0.766(6) 1 d PDU A 1 H16R H 0.8778 0.6157 0.0987 0.079 Uiso 0.766(6) 1 calc PR A 1 C17R C 0.7319(13) 0.6719(4) 0.1778(3) 0.0599(19) Uani 0.766(6) 1 d PD A 1 H17R H 0.6364 0.7162 0.1816 0.072 Uiso 0.766(6) 1 calc PR A 1 C18R C 0.9409(13) 0.6890(6) 0.2170(3) 0.081(2) Uani 0.766(6) 1 d PD A 1 H18A H 1.0113 0.7327 0.1964 0.098 Uiso 0.766(6) 1 calc PR A 1 H18B H 1.0390 0.6462 0.2128 0.098 Uiso 0.766(6) 1 calc PR A 1 C19R C 0.9006(15) 0.7050(5) 0.2929(3) 0.094(2) Uani 0.766(6) 1 d PD A 1 H19A H 1.0388 0.7121 0.3161 0.113 Uiso 0.766(6) 1 calc PR A 1 H19B H 0.8171 0.7515 0.2976 0.113 Uiso 0.766(6) 1 calc PR A 1 C20R C 0.7778(12) 0.6400(5) 0.3260(3) 0.105(2) Uani 0.766(6) 1 d PDU A 1 H20A H 0.8715 0.5958 0.3279 0.127 Uiso 0.766(6) 1 calc PR A 1 H20B H 0.7402 0.6538 0.3728 0.127 Uiso 0.766(6) 1 calc PR A 1 C21R C 0.5759(13) 0.6207(6) 0.2878(3) 0.116(3) Uani 0.766(6) 1 d PDU A 1 H21A H 0.4733 0.6622 0.2920 0.139 Uiso 0.766(6) 1 calc PR A 1 H21B H 0.5102 0.5761 0.3084 0.139 Uiso 0.766(6) 1 calc PR A 1 C22R C 0.6178(14) 0.6052(6) 0.2117(4) 0.087(2) Uani 0.766(6) 1 d PD A 1 H22A H 0.7070 0.5601 0.2071 0.104 Uiso 0.766(6) 1 calc PR A 1 H22B H 0.4803 0.5959 0.1887 0.104 Uiso 0.766(6) 1 calc PR A 1 C23R C 0.5718(15) 0.6342(5) 0.0619(4) 0.086(2) Uani 0.766(6) 1 d PD A 1 H23A H 0.6127 0.6224 0.0155 0.129 Uiso 0.766(6) 1 calc PR A 1 H23B H 0.4692 0.6753 0.0617 0.129 Uiso 0.766(6) 1 calc PR A 1 H23C H 0.5066 0.5905 0.0828 0.129 Uiso 0.766(6) 1 calc PR A 1 O1R O 0.9429(9) 1.0039(3) 0.3493(2) 0.127(2) Uani 0.766(6) 1 d PD A 1 O2R O 0.2211(12) 0.8171(7) 0.1064(5) 0.105(5) Uani 0.766(6) 1 d PD A 1 O3R O 0.5422(15) 0.8282(8) 0.0569(4) 0.073(3) Uani 0.766(6) 1 d PD A 1 N1R N 0.8693(18) 0.7252(6) 0.0682(4) 0.059(2) Uani 0.766(6) 1 d PDU A 1 H1R1 H 0.8914 0.7153 0.0239 0.088 Uiso 0.766(6) 1 calc PR A 1 H1R2 H 0.9957 0.7364 0.0881 0.088 Uiso 0.766(6) 1 calc PR A 1 H1R3 H 0.7788 0.7644 0.0722 0.088 Uiso 0.766(6) 1 calc PR A 1 C1P C 0.782(3) 0.9712(11) 0.4754(7) 0.080(9) Uiso 0.234(6) 1 d PD A 2 H1P H 0.7772 1.0267 0.4768 0.096 Uiso 0.234(6) 1 calc PR A 2 C2P C 1.003(2) 0.9457(9) 0.4451(6) 0.079(5) Uiso 0.234(6) 1 d PD A 2 H2P H 1.1165 0.9827 0.4568 0.095 Uiso 0.234(6) 1 calc PR A 2 C3P C 1.070(4) 0.8681(13) 0.4693(15) 0.125(9) Uiso 0.234(6) 1 d PDU A 2 H3P H 1.2051 0.8491 0.4566 0.149 Uiso 0.234(6) 1 calc PR A 2 C4P C 0.940(3) 0.8259(9) 0.5083(10) 0.100(6) Uiso 0.234(6) 1 d PD A 2 H4P H 0.9541 0.7734 0.5055 0.120 Uiso 0.234(6) 1 calc PR A 2 C5P C 0.775(4) 0.8573(12) 0.5562(13) 0.127(8) Uiso 0.234(6) 1 d PDU A 2 H5P1 H 0.8264 0.8501 0.6029 0.152 Uiso 0.234(6) 1 calc PR A 2 H5P2 H 0.6416 0.8286 0.5511 0.152 Uiso 0.234(6) 1 calc PR A 2 C6P C 0.726(5) 0.9401(13) 0.5457(9) 0.121(10) Uiso 0.234(6) 1 d PDU A 2 H6P1 H 0.8042 0.9692 0.5800 0.145 Uiso 0.234(6) 1 calc PR A 2 H6P2 H 0.5713 0.9481 0.5537 0.145 Uiso 0.234(6) 1 calc PR A 2 C7P C 0.627(2) 0.9430(17) 0.4213(8) 0.092(8) Uiso 0.234(6) 1 d PDU A 2 H7P H 0.4804 0.9312 0.4265 0.111 Uiso 0.234(6) 1 calc PR A 2 C8P C 0.747(2) 0.9389(13) 0.3645(7) 0.066(7) Uiso 0.234(6) 1 d PD A 2 C9P C 0.658(3) 0.9149(10) 0.2948(7) 0.076(12) Uiso 0.234(6) 1 d PD A 2 C10P C 0.766(3) 0.9353(15) 0.2344(8) 0.054(8) Uiso 0.234(6) 1 d PD A 2 H10P H 0.8903 0.9651 0.2364 0.065 Uiso 0.234(6) 1 calc PR A 2 C11P C 0.687(3) 0.9112(12) 0.1713(8) 0.036(5) Uiso 0.234(6) 1 d PD A 2 H11P H 0.7621 0.9219 0.1310 0.043 Uiso 0.234(6) 1 calc PR A 2 C12P C 0.492(5) 0.870(3) 0.1698(9) 0.051(15) Uiso 0.234(6) 1 d PD A 2 C13P C 0.393(4) 0.8480(14) 0.2305(9) 0.070(9) Uiso 0.234(6) 1 d PD A 2 H13P H 0.2756 0.8146 0.2287 0.084 Uiso 0.234(6) 1 calc PR A 2 C14P C 0.465(4) 0.8743(16) 0.2933(9) 0.099(14) Uiso 0.234(6) 1 d PD A 2 H14P H 0.3858 0.8651 0.3333 0.119 Uiso 0.234(6) 1 calc PR A 2 C15P C 0.395(4) 0.844(2) 0.1020(10) 0.064(14) Uiso 0.234(6) 1 d PD A 2 C16P C 0.816(4) 0.6520(15) 0.1057(9) 0.046(5) Uiso 0.234(6) 1 d PDU A 2 H16P H 0.9320 0.6139 0.1063 0.055 Uiso 0.234(6) 1 calc PR A 2 C17P C 0.778(4) 0.6792(17) 0.1796(10) 0.067(9) Uiso 0.234(6) 1 d PD A 2 H17P H 0.6940 0.7264 0.1763 0.081 Uiso 0.234(6) 1 calc PR A 2 C18P C 0.990(4) 0.6994(18) 0.2158(11) 0.076(9) Uiso 0.234(6) 1 d PD A 2 H18C H 1.0598 0.7407 0.1913 0.092 Uiso 0.234(6) 1 calc PR A 2 H18D H 1.0870 0.6560 0.2141 0.092 Uiso 0.234(6) 1 calc PR A 2 C19P C 0.958(4) 0.7229(16) 0.2911(12) 0.093(9) Uiso 0.234(6) 1 d PD A 2 H19C H 1.0981 0.7315 0.3126 0.111 Uiso 0.234(6) 1 calc PR A 2 H19D H 0.8753 0.7698 0.2933 0.111 Uiso 0.234(6) 1 calc PR A 2 C20P C 0.837(4) 0.6607(18) 0.3290(12) 0.113(5) Uiso 0.234(6) 1 d PDU A 2 H20C H 0.9216 0.6143 0.3280 0.136 Uiso 0.234(6) 1 calc PR A 2 H20D H 0.8167 0.6753 0.3767 0.136 Uiso 0.234(6) 1 calc PR A 2 C21P C 0.617(4) 0.6470(19) 0.2960(12) 0.118(8) Uiso 0.234(6) 1 d PDU A 2 H21C H 0.5301 0.6928 0.2991 0.142 Uiso 0.234(6) 1 calc PR A 2 H21D H 0.5414 0.6072 0.3209 0.142 Uiso 0.234(6) 1 calc PR A 2 C22P C 0.639(5) 0.6239(18) 0.2206(12) 0.087(11) Uiso 0.234(6) 1 d PD A 2 H22C H 0.7043 0.5738 0.2180 0.104 Uiso 0.234(6) 1 calc PR A 2 H22D H 0.4957 0.6211 0.2000 0.104 Uiso 0.234(6) 1 calc PR A 2 C23P C 0.619(4) 0.6177(16) 0.0695(14) 0.073(9) Uiso 0.234(6) 1 d PD A 2 H23D H 0.6576 0.6048 0.0231 0.110 Uiso 0.234(6) 1 calc PR A 2 H23E H 0.5022 0.6539 0.0690 0.110 Uiso 0.234(6) 1 calc PR A 2 H23F H 0.5733 0.5728 0.0934 0.110 Uiso 0.234(6) 1 calc PR A 2 O1P O 0.9694(17) 0.9446(8) 0.3698(5) 0.084(4) Uiso 0.234(6) 1 d PD A 2 O2P O 0.208(4) 0.8165(14) 0.1048(15) 0.075(10) Uiso 0.234(6) 1 d PD A 2 O3P O 0.523(5) 0.837(2) 0.0515(13) 0.061(8) Uiso 0.234(6) 1 d PD A 2 N1P N 0.890(6) 0.7178(19) 0.0620(14) 0.051(7) Uiso 0.234(6) 1 d PDU A 2 H1P1 H 0.9833 0.7461 0.0856 0.076 Uiso 0.234(6) 1 calc PR A 2 H1P2 H 0.7750 0.7458 0.0502 0.076 Uiso 0.234(6) 1 calc PR A 2 H1P3 H 0.9543 0.7003 0.0242 0.076 Uiso 0.234(6) 1 calc PR A 2 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 C1R 0.091(4) 0.072(4) 0.070(4) -0.013(3) -0.028(3) 0.001(3) C2R 0.083(4) 0.128(6) 0.098(5) 0.006(4) -0.009(3) -0.001(4) C3R 0.106(5) 0.128(6) 0.092(4) 0.001(4) 0.003(4) 0.028(5) C4R 0.129(5) 0.075(3) 0.067(3) -0.006(2) 0.001(3) -0.007(3) C5R 0.150(5) 0.097(4) 0.066(3) 0.010(3) 0.009(4) -0.016(4) C6R 0.132(6) 0.125(6) 0.054(3) -0.013(3) -0.008(3) 0.004(4) C7R 0.085(4) 0.076(3) 0.053(3) -0.016(2) 0.000(3) -0.010(3) C8R 0.095(4) 0.070(4) 0.072(4) 0.000(3) -0.006(3) -0.006(4) C9R 0.067(3) 0.050(3) 0.057(4) -0.0069(19) -0.010(2) -0.003(2) C10R 0.051(3) 0.083(5) 0.069(4) -0.014(3) -0.005(2) -0.005(4) C11R 0.067(4) 0.057(4) 0.066(4) -0.003(2) -0.006(3) 0.004(3) C12R 0.056(5) 0.054(5) 0.067(6) -0.005(2) 0.000(2) 0.000(3) C13R 0.061(3) 0.063(4) 0.063(4) -0.023(2) 0.011(2) -0.013(3) C14R 0.083(4) 0.062(4) 0.053(3) -0.016(2) 0.020(2) -0.012(3) C15R 0.067(4) 0.064(4) 0.049(4) -0.006(3) -0.013(3) 0.006(3) C16R 0.073(5) 0.065(3) 0.060(3) 0.005(2) 0.001(3) 0.002(4) C17R 0.063(3) 0.061(3) 0.056(3) 0.0062(19) 0.005(2) -0.002(3) C18R 0.086(4) 0.106(5) 0.052(3) 0.006(2) -0.005(3) -0.035(4) C19R 0.122(6) 0.112(6) 0.047(3) 0.002(3) -0.003(3) -0.031(5) C20R 0.128(6) 0.133(6) 0.055(3) 0.030(3) 0.003(3) -0.013(4) C21R 0.128(5) 0.159(8) 0.060(3) 0.022(4) 0.018(4) -0.043(5) C22R 0.097(5) 0.091(6) 0.072(4) 0.015(4) 0.009(3) -0.026(4) C23R 0.097(5) 0.078(4) 0.083(4) 0.008(4) -0.024(4) -0.027(4) O1R 0.163(4) 0.137(4) 0.080(3) -0.015(3) -0.009(3) -0.086(4) O2R 0.073(4) 0.159(8) 0.082(4) -0.029(3) -0.012(2) -0.045(3) O3R 0.076(3) 0.090(5) 0.052(3) -0.011(3) -0.014(2) 0.010(3) N1R 0.057(4) 0.075(4) 0.044(3) -0.013(2) 0.0015(19) -0.002(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 C1R C2R 1.490(7) . ? C1R C7R 1.536(7) . ? C1R C6R 1.569(7) . ? C2R C3R 1.330(8) . ? C3R C4R 1.519(8) . ? C4R C5R 1.552(6) . ? C4R C7R 1.562(7) . ? C5R C6R 1.543(7) . ? C7R C8R 1.491(6) . ? C8R O1R 1.216(7) . ? C8R C9R 1.497(6) . ? C9R C10R 1.389(6) . ? C9R C14R 1.394(7) . ? C10R C11R 1.368(5) . ? C11R C12R 1.394(7) . ? C12R C13R 1.373(6) . ? C12R C15R 1.509(6) . ? C13R C14R 1.385(6) . ? C15R O2R 1.245(6) . ? C15R O3R 1.253(5) . ? C16R N1R 1.494(6) . ? C16R C23R 1.514(7) . ? C16R C17R 1.515(6) . ? C17R C22R 1.518(7) . ? C17R C18R 1.523(7) . ? C18R C19R 1.524(6) . ? C19R C20R 1.516(7) . ? C20R C21R 1.486(7) . ? C21R C22R 1.527(7) . ? C1P C7P 1.505(10) . ? C1P C6P 1.515(9) . ? C1P C2P 1.547(9) . ? C2P O1P 1.479(9) . ? C2P C3P 1.503(10) . ? C3P C4P 1.327(10) . ? C4P C5P 1.484(10) . ? C5P C6P 1.505(10) . ? C7P C8P 1.330(9) . ? C8P O1P 1.376(9) . ? C8P C9P 1.521(9) . ? C9P C14P 1.390(9) . ? C9P C10P 1.395(9) . ? C10P C11P 1.386(9) . ? C11P C12P 1.394(9) . ? C12P C13P 1.388(9) . ? C12P C15P 1.522(9) . ? C13P C14P 1.381(9) . ? C15P O2P 1.246(10) . ? C15P O3P 1.266(10) . ? C16P N1P 1.509(10) . ? C16P C23P 1.523(10) . ? C16P C17P 1.534(10) . ? C17P C22P 1.520(10) . ? C17P C18P 1.523(10) . ? C18P C19P 1.537(10) . ? C19P C20P 1.516(10) . ? C20P C21P 1.514(10) . ? C21P C22P 1.531(10) . ? 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 C2R C1R C7R 104.0(4) . . ? C2R C1R C6R 103.1(5) . . ? C7R C1R C6R 99.7(5) . . ? C3R C2R C1R 107.6(5) . . ? C2R C3R C4R 107.5(5) . . ? C3R C4R C5R 103.8(5) . . ? C3R C4R C7R 101.6(5) . . ? C5R C4R C7R 100.0(4) . . ? C6R C5R C4R 103.0(4) . . ? C5R C6R C1R 102.7(4) . . ? C8R C7R C1R 113.8(5) . . ? C8R C7R C4R 114.4(5) . . ? C1R C7R C4R 92.5(4) . . ? O1R C8R C7R 121.2(5) . . ? O1R C8R C9R 119.6(5) . . ? C7R C8R C9R 119.3(5) . . ? C10R C9R C14R 118.0(4) . . ? C10R C9R C8R 117.9(6) . . ? C14R C9R C8R 124.0(5) . . ? C11R C10R C9R 121.3(6) . . ? C10R C11R C12R 120.0(6) . . ? C13R C12R C11R 119.6(5) . . ? C13R C12R C15R 120.5(5) . . ? C11R C12R C15R 119.7(5) . . ? C12R C13R C14R 120.0(5) . . ? C13R C14R C9R 120.8(4) . . ? O2R C15R O3R 123.7(6) . . ? O2R C15R C12R 118.2(5) . . ? O3R C15R C12R 118.0(6) . . ? N1R C16R C23R 108.0(5) . . ? N1R C16R C17R 111.0(5) . . ? C23R C16R C17R 114.6(6) . . ? C16R C17R C22R 111.4(5) . . ? C16R C17R C18R 112.5(5) . . ? C22R C17R C18R 109.0(5) . . ? C17R C18R C19R 112.6(6) . . ? C20R C19R C18R 110.7(6) . . ? C21R C20R C19R 112.1(5) . . ? C20R C21R C22R 112.7(6) . . ? C17R C22R C21R 111.2(6) . . ? C7P C1P C6P 111.6(14) . . ? C7P C1P C2P 101.1(9) . . ? C6P C1P C2P 116.3(12) . . ? O1P C2P C3P 109.7(13) . . ? O1P C2P C1P 105.0(8) . . ? C3P C2P C1P 112.4(10) . . ? C4P C3P C2P 121.9(12) . . ? C3P C4P C5P 124.0(13) . . ? C4P C5P C6P 114.6(11) . . ? C5P C6P C1P 115.2(11) . . ? C8P C7P C1P 104.6(9) . . ? C7P C8P O1P 118.8(9) . . ? C7P C8P C9P 124.2(10) . . ? O1P C8P C9P 116.2(9) . . ? C14P C9P C10P 121.3(10) . . ? C14P C9P C8P 117.8(11) . . ? C10P C9P C8P 120.9(11) . . ? C11P C10P C9P 120.2(11) . . ? C10P C11P C12P 118.4(11) . . ? C13P C12P C11P 120.5(11) . . ? C13P C12P C15P 118.5(11) . . ? C11P C12P C15P 120.8(11) . . ? C14P C13P C12P 121.2(12) . . ? C13P C14P C9P 117.6(12) . . ? O2P C15P O3P 124.6(16) . . ? O2P C15P C12P 116.3(13) . . ? O3P C15P C12P 117.3(14) . . ? N1P C16P C23P 106.4(13) . . ? N1P C16P C17P 109.5(14) . . ? C23P C16P C17P 116.0(14) . . ? C22P C17P C18P 112.7(13) . . ? C22P C17P C16P 112.1(13) . . ? C18P C17P C16P 112.2(13) . . ? C17P C18P C19P 113.2(12) . . ? C20P C19P C18P 109.5(13) . . ? C21P C20P C19P 110.3(13) . . ? C20P C21P C22P 111.7(14) . . ? C17P C22P C21P 112.6(13) . . ? C8P O1P C2P 102.5(8) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.235 _refine_diff_density_min -0.158 _refine_diff_density_rms 0.048 #===END data_25.1%P _database_code_depnum_ccdc_archive 'CCDC 608921' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1508(9) _cell_length_b 17.596(2) _cell_length_c 19.478(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2108.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9775 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11370 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3684 _reflns_number_gt 2297 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.1568P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.018(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3684 _refine_ls_number_parameters 354 _refine_ls_number_restraints 201 _refine_ls_R_factor_all 0.1046 _refine_ls_R_factor_gt 0.0730 _refine_ls_wR_factor_ref 0.2283 _refine_ls_wR_factor_gt 0.2058 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1R C 0.8352(13) 0.9760(4) 0.4837(3) 0.083(3) Uani 0.749(7) 1 d PD A 1 H1R H 0.8376 1.0317 0.4833 0.100 Uiso 0.749(7) 1 calc PR A 1 C2R C 1.0506(11) 0.9374(5) 0.4834(5) 0.113(3) Uani 0.749(7) 1 d PD A 1 H2R H 1.1820 0.9593 0.4963 0.136 Uiso 0.749(7) 1 calc PR A 1 C3R C 1.0240(14) 0.8665(6) 0.4616(5) 0.112(4) Uani 0.749(7) 1 d PD A 1 H3R H 1.1323 0.8303 0.4555 0.135 Uiso 0.749(7) 1 calc PR A 1 C4R C 0.7809(11) 0.8561(3) 0.4486(3) 0.101(2) Uani 0.749(7) 1 d PD A 1 H4R H 0.7394 0.8140 0.4184 0.121 Uiso 0.749(7) 1 calc PR A 1 C5R C 0.6851(17) 0.8548(4) 0.5228(4) 0.114(3) Uani 0.749(7) 1 d PD A 1 H5R1 H 0.5320 0.8416 0.5225 0.137 Uiso 0.749(7) 1 calc PR A 1 H5R2 H 0.7629 0.8192 0.5519 0.137 Uiso 0.749(7) 1 calc PR A 1 C6R C 0.720(2) 0.9375(5) 0.5469(3) 0.111(3) Uani 0.749(7) 1 d PDU A 1 H6R1 H 0.8114 0.9394 0.5874 0.133 Uiso 0.749(7) 1 calc PR A 1 H6R2 H 0.5823 0.9621 0.5570 0.133 Uiso 0.749(7) 1 calc PR A 1 C7R C 0.7094(13) 0.9376(4) 0.4252(2) 0.0782(18) Uani 0.749(7) 1 d PDU A 1 H7R H 0.5521 0.9450 0.4296 0.094 Uiso 0.749(7) 1 calc PR A 1 C8R C 0.7908(12) 0.9599(4) 0.3558(3) 0.086(2) Uani 0.749(7) 1 d PD A 1 C9R C 0.6859(11) 0.9264(4) 0.2937(3) 0.062(2) Uani 0.749(7) 1 d PD A 1 C10R C 0.8077(15) 0.9249(7) 0.2332(4) 0.077(3) Uani 0.749(7) 1 d PD A 1 H10R H 0.9484 0.9442 0.2332 0.092 Uiso 0.749(7) 1 calc PR A 1 C11R C 0.7228(16) 0.8954(7) 0.1739(4) 0.072(3) Uani 0.749(7) 1 d PD A 1 H11R H 0.8082 0.8927 0.1346 0.087 Uiso 0.749(7) 1 calc PR A 1 C12R C 0.5085(18) 0.8694(9) 0.1724(4) 0.062(5) Uani 0.749(7) 1 d PD A 1 C13R C 0.3872(10) 0.8698(4) 0.2314(3) 0.0636(18) Uani 0.749(7) 1 d PDU A 1 H13R H 0.2450 0.8518 0.2308 0.076 Uiso 0.749(7) 1 calc PR A 1 C14R C 0.4765(10) 0.8969(4) 0.2919(3) 0.0715(19) Uani 0.749(7) 1 d PDU A 1 H14R H 0.3949 0.8953 0.3320 0.086 Uiso 0.749(7) 1 calc PR A 1 C15R C 0.4175(15) 0.8348(9) 0.1078(4) 0.061(4) Uani 0.749(7) 1 d PD A 1 C16R C 0.7750(17) 0.6556(7) 0.1017(4) 0.071(3) Uani 0.749(7) 1 d PDU A 1 H16R H 0.8791 0.6136 0.0983 0.085 Uiso 0.749(7) 1 calc PR A 1 C17R C 0.7342(14) 0.6710(5) 0.1776(3) 0.063(2) Uani 0.749(7) 1 d PD A 1 H17R H 0.6391 0.7155 0.1809 0.075 Uiso 0.749(7) 1 calc PR A 1 C18R C 0.9429(14) 0.6890(6) 0.2163(3) 0.084(3) Uani 0.749(7) 1 d PD A 1 H18A H 1.0114 0.7331 0.1956 0.100 Uiso 0.749(7) 1 calc PR A 1 H18B H 1.0423 0.6465 0.2119 0.100 Uiso 0.749(7) 1 calc PR A 1 C19R C 0.9026(16) 0.7048(5) 0.2925(3) 0.095(2) Uani 0.749(7) 1 d PDU A 1 H19A H 1.0406 0.7122 0.3156 0.114 Uiso 0.749(7) 1 calc PR A 1 H19B H 0.8184 0.7512 0.2973 0.114 Uiso 0.749(7) 1 calc PR A 1 C20R C 0.7811(15) 0.6394(6) 0.3259(3) 0.114(3) Uani 0.749(7) 1 d PDU A 1 H20A H 0.8747 0.5951 0.3274 0.136 Uiso 0.749(7) 1 calc PR A 1 H20B H 0.7443 0.6530 0.3727 0.136 Uiso 0.749(7) 1 calc PR A 1 C21R C 0.5783(14) 0.6204(7) 0.2875(3) 0.123(3) Uani 0.749(7) 1 d PDU A 1 H21A H 0.4765 0.6622 0.2919 0.147 Uiso 0.749(7) 1 calc PR A 1 H21B H 0.5120 0.5759 0.3081 0.147 Uiso 0.749(7) 1 calc PR A 1 C22R C 0.6182(16) 0.6049(6) 0.2114(4) 0.088(3) Uani 0.749(7) 1 d PD A 1 H22A H 0.7054 0.5593 0.2064 0.106 Uiso 0.749(7) 1 calc PR A 1 H22B H 0.4803 0.5963 0.1885 0.106 Uiso 0.749(7) 1 calc PR A 1 C23R C 0.5728(18) 0.6337(7) 0.0616(5) 0.093(3) Uani 0.749(7) 1 d PD A 1 H23A H 0.6123 0.6217 0.0151 0.140 Uiso 0.749(7) 1 calc PR A 1 H23B H 0.4720 0.6753 0.0617 0.140 Uiso 0.749(7) 1 calc PR A 1 H23C H 0.5062 0.5901 0.0825 0.140 Uiso 0.749(7) 1 calc PR A 1 O1R O 0.9430(11) 1.0033(4) 0.3488(3) 0.138(3) Uani 0.749(7) 1 d PD A 1 O2R O 0.2262(11) 0.8121(6) 0.1073(4) 0.087(2) Uani 0.749(7) 1 d PD A 1 O3R O 0.5442(12) 0.8265(5) 0.0574(3) 0.073(2) Uani 0.749(7) 1 d PD A 1 N1R N 0.874(3) 0.7235(9) 0.0685(6) 0.070(4) Uani 0.749(7) 1 d PDU A 1 H1R1 H 0.8964 0.7140 0.0242 0.105 Uiso 0.749(7) 1 calc PR A 1 H1R2 H 1.0002 0.7342 0.0887 0.105 Uiso 0.749(7) 1 calc PR A 1 H1R3 H 0.7846 0.7630 0.0727 0.105 Uiso 0.749(7) 1 calc PR A 1 C1P C 0.783(3) 0.9707(12) 0.4754(8) 0.088(10) Uiso 0.251(7) 1 d PD A 2 H1P H 0.7755 1.0263 0.4762 0.105 Uiso 0.251(7) 1 calc PR A 2 C2P C 1.005(2) 0.9456(9) 0.4453(6) 0.080(6) Uiso 0.251(7) 1 d PD A 2 H2P H 1.1177 0.9828 0.4568 0.096 Uiso 0.251(7) 1 calc PR A 2 C3P C 1.070(4) 0.8677(15) 0.4697(15) 0.135(18) Uiso 0.251(7) 1 d PD A 2 H3P H 1.2052 0.8485 0.4571 0.162 Uiso 0.251(7) 1 calc PR A 2 C4P C 0.941(3) 0.8258(10) 0.5087(10) 0.100(7) Uiso 0.251(7) 1 d PD A 2 H4P H 0.9561 0.7733 0.5062 0.120 Uiso 0.251(7) 1 calc PR A 2 C5P C 0.773(5) 0.8561(13) 0.5561(15) 0.142(12) Uiso 0.251(7) 1 d PD A 2 H5P1 H 0.8192 0.8475 0.6031 0.171 Uiso 0.251(7) 1 calc PR A 2 H5P2 H 0.6383 0.8284 0.5491 0.171 Uiso 0.251(7) 1 calc PR A 2 C6P C 0.730(5) 0.9399(14) 0.5462(9) 0.127(9) Uiso 0.251(7) 1 d PDU A 2 H6P1 H 0.8144 0.9679 0.5798 0.152 Uiso 0.251(7) 1 calc PR A 2 H6P2 H 0.5776 0.9496 0.5556 0.152 Uiso 0.251(7) 1 calc PR A 2 C7P C 0.629(3) 0.9408(19) 0.4221(9) 0.100(8) Uiso 0.251(7) 1 d PDU A 2 H7P H 0.4834 0.9277 0.4279 0.119 Uiso 0.251(7) 1 calc PR A 2 C8P C 0.746(2) 0.9370(11) 0.3647(7) 0.057(5) Uiso 0.251(7) 1 d PD A 2 C9P C 0.657(3) 0.9127(9) 0.2952(7) 0.084(12) Uiso 0.251(7) 1 d PD A 2 C10P C 0.767(3) 0.9325(16) 0.2350(8) 0.051(7) Uiso 0.251(7) 1 d PD A 2 H10P H 0.8913 0.9625 0.2371 0.061 Uiso 0.251(7) 1 calc PR A 2 C11P C 0.690(4) 0.9073(17) 0.1722(8) 0.039(6) Uiso 0.251(7) 1 d PD A 2 H11P H 0.7689 0.9159 0.1323 0.046 Uiso 0.251(7) 1 calc PR A 2 C12P C 0.492(5) 0.869(3) 0.1696(8) 0.056(15) Uiso 0.251(7) 1 d PD A 2 C13P C 0.390(4) 0.8464(14) 0.2298(9) 0.077(7) Uiso 0.251(7) 1 d PDU A 2 H13P H 0.2714 0.8137 0.2278 0.092 Uiso 0.251(7) 1 calc PR A 2 C14P C 0.463(3) 0.8723(15) 0.2927(9) 0.087(8) Uiso 0.251(7) 1 d PDU A 2 H14P H 0.3846 0.8627 0.3325 0.104 Uiso 0.251(7) 1 calc PR A 2 C15P C 0.397(4) 0.844(3) 0.1013(9) 0.067(16) Uiso 0.251(7) 1 d PD A 2 C16P C 0.809(5) 0.6567(17) 0.1061(10) 0.056(6) Uiso 0.251(7) 1 d PDU A 2 H16P H 0.9267 0.6193 0.1049 0.067 Uiso 0.251(7) 1 calc PR A 2 C17P C 0.779(4) 0.6806(17) 0.1812(10) 0.077(10) Uiso 0.251(7) 1 d PD A 2 H17P H 0.6939 0.7276 0.1812 0.093 Uiso 0.251(7) 1 calc PR A 2 C18P C 0.996(4) 0.699(2) 0.2159(12) 0.089(10) Uiso 0.251(7) 1 d PD A 2 H18C H 1.0652 0.7403 0.1920 0.107 Uiso 0.251(7) 1 calc PR A 2 H18D H 1.0906 0.6546 0.2123 0.107 Uiso 0.251(7) 1 calc PR A 2 C19P C 0.970(5) 0.7197(19) 0.2920(13) 0.109(8) Uiso 0.251(7) 1 d PDU A 2 H19C H 1.1118 0.7262 0.3127 0.130 Uiso 0.251(7) 1 calc PR A 2 H19D H 0.8920 0.7675 0.2957 0.130 Uiso 0.251(7) 1 calc PR A 2 C20P C 0.846(5) 0.658(2) 0.3301(13) 0.132(9) Uiso 0.251(7) 1 d PDU A 2 H20C H 0.9297 0.6117 0.3300 0.158 Uiso 0.251(7) 1 calc PR A 2 H20D H 0.8248 0.6738 0.3775 0.158 Uiso 0.251(7) 1 calc PR A 2 C21P C 0.627(4) 0.644(2) 0.2971(13) 0.121(9) Uiso 0.251(7) 1 d PDU A 2 H21C H 0.5385 0.6896 0.3005 0.145 Uiso 0.251(7) 1 calc PR A 2 H21D H 0.5523 0.6037 0.3217 0.145 Uiso 0.251(7) 1 calc PR A 2 C22P C 0.650(5) 0.6216(19) 0.2214(12) 0.097(12) Uiso 0.251(7) 1 d PD A 2 H22C H 0.7227 0.5728 0.2183 0.116 Uiso 0.251(7) 1 calc PR A 2 H22D H 0.5068 0.6164 0.2011 0.116 Uiso 0.251(7) 1 calc PR A 2 C23P C 0.614(5) 0.6207(19) 0.0708(15) 0.075(9) Uiso 0.251(7) 1 d PD A 2 H23D H 0.6517 0.6077 0.0245 0.112 Uiso 0.251(7) 1 calc PR A 2 H23E H 0.4950 0.6561 0.0705 0.112 Uiso 0.251(7) 1 calc PR A 2 H23F H 0.5718 0.5756 0.0952 0.112 Uiso 0.251(7) 1 calc PR A 2 O1P O 0.9688(17) 0.9436(8) 0.3701(5) 0.083(4) Uiso 0.251(7) 1 d PD A 2 O2P O 0.198(3) 0.8334(16) 0.0983(13) 0.084(9) Uiso 0.251(7) 1 d PD A 2 O3P O 0.523(3) 0.8419(14) 0.0500(10) 0.057(6) Uiso 0.251(7) 1 d PD A 2 N1P N 0.879(6) 0.7230(19) 0.0628(15) 0.045(8) Uiso 0.251(7) 1 d PDU A 2 H1P1 H 0.9730 0.7513 0.0864 0.067 Uiso 0.251(7) 1 calc PR A 2 H1P2 H 0.7638 0.7508 0.0517 0.067 Uiso 0.251(7) 1 calc PR A 2 H1P3 H 0.9429 0.7060 0.0248 0.067 Uiso 0.251(7) 1 calc PR A 2 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 C1R 0.097(5) 0.081(5) 0.072(4) -0.012(3) -0.032(4) -0.002(4) C2R 0.093(5) 0.130(7) 0.116(7) 0.016(6) -0.008(5) 0.003(5) C3R 0.111(6) 0.131(9) 0.095(6) 0.000(5) -0.001(5) 0.028(6) C4R 0.142(6) 0.084(4) 0.077(4) -0.005(3) 0.002(4) -0.003(4) C5R 0.170(7) 0.100(5) 0.072(4) 0.019(4) 0.013(5) -0.017(5) C6R 0.138(6) 0.132(7) 0.063(4) -0.013(4) -0.005(4) 0.005(5) C7R 0.094(5) 0.085(4) 0.056(3) -0.019(3) 0.004(3) -0.014(4) C8R 0.102(5) 0.072(5) 0.084(4) 0.006(3) -0.004(4) -0.015(4) C9R 0.072(4) 0.052(3) 0.061(4) -0.008(2) -0.012(3) -0.003(3) C10R 0.059(4) 0.096(6) 0.075(5) -0.017(3) -0.007(3) -0.002(4) C11R 0.078(5) 0.071(6) 0.067(4) -0.005(3) -0.008(3) 0.001(5) C12R 0.058(6) 0.061(6) 0.068(6) -0.005(3) -0.001(2) -0.002(3) C13R 0.065(3) 0.064(4) 0.062(3) -0.025(3) 0.011(2) -0.015(3) C14R 0.090(4) 0.063(4) 0.061(3) -0.017(3) 0.024(3) -0.011(3) C15R 0.066(5) 0.068(5) 0.049(4) -0.005(3) -0.010(3) 0.010(4) C16R 0.084(6) 0.066(4) 0.062(4) 0.004(2) 0.000(3) -0.007(4) C17R 0.069(4) 0.058(4) 0.062(4) 0.002(2) 0.003(3) -0.002(3) C18R 0.087(5) 0.112(6) 0.051(3) 0.007(3) -0.005(3) -0.041(5) C19R 0.117(6) 0.121(6) 0.048(3) 0.000(3) -0.003(4) -0.026(5) C20R 0.131(7) 0.156(8) 0.054(3) 0.035(4) -0.005(4) -0.023(6) C21R 0.129(6) 0.172(9) 0.067(4) 0.025(5) 0.016(4) -0.046(6) C22R 0.094(5) 0.101(6) 0.070(4) 0.012(4) 0.003(4) -0.034(5) C23R 0.103(6) 0.087(6) 0.089(6) 0.008(4) -0.032(5) -0.032(5) O1R 0.181(6) 0.144(5) 0.088(3) -0.018(3) -0.009(3) -0.088(5) O2R 0.071(3) 0.115(7) 0.075(3) -0.010(4) -0.015(2) -0.026(4) O3R 0.081(4) 0.080(5) 0.057(3) -0.006(3) -0.016(2) 0.015(3) N1R 0.071(5) 0.093(6) 0.047(4) -0.011(3) -0.002(2) -0.004(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 C1R C2R 1.489(8) . ? C1R C7R 1.534(7) . ? C1R C6R 1.574(7) . ? C2R C3R 1.326(8) . ? C3R C4R 1.528(9) . ? C4R C5R 1.562(7) . ? C4R C7R 1.567(7) . ? C5R C6R 1.544(8) . ? C7R C8R 1.496(7) . ? C8R O1R 1.215(7) . ? C8R C9R 1.493(6) . ? C9R C14R 1.389(7) . ? C9R C10R 1.396(7) . ? C10R C11R 1.369(6) . ? C11R C12R 1.396(7) . ? C12R C13R 1.370(6) . ? C12R C15R 1.505(7) . ? C13R C14R 1.386(6) . ? C15R O2R 1.243(6) . ? C15R O3R 1.262(6) . ? C16R N1R 1.489(7) . ? C16R C23R 1.520(8) . ? C16R C17R 1.523(6) . ? C17R C22R 1.514(7) . ? C17R C18R 1.522(8) . ? C18R C19R 1.531(7) . ? C19R C20R 1.518(8) . ? C20R C21R 1.493(8) . ? C21R C22R 1.527(8) . ? C1P C7P 1.501(10) . ? C1P C6P 1.517(9) . ? C1P C2P 1.550(9) . ? C2P O1P 1.482(9) . ? C2P C3P 1.506(10) . ? C3P C4P 1.325(10) . ? C4P C5P 1.484(10) . ? C5P C6P 1.509(10) . ? C7P C8P 1.330(9) . ? C8P O1P 1.382(9) . ? C8P C9P 1.521(8) . ? C9P C14P 1.387(9) . ? C9P C10P 1.399(9) . ? C10P C11P 1.385(9) . ? C11P C12P 1.394(9) . ? C12P C13P 1.386(9) . ? C12P C15P 1.517(9) . ? C13P C14P 1.384(9) . ? C15P O2P 1.243(9) . ? C15P O3P 1.266(9) . ? C16P N1P 1.503(10) . ? C16P C23P 1.520(10) . ? C16P C17P 1.533(10) . ? C17P C22P 1.523(10) . ? C17P C18P 1.527(10) . ? C18P C19P 1.537(10) . ? C19P C20P 1.516(10) . ? C20P C21P 1.515(10) . ? C21P C22P 1.534(10) . ? 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 C2R C1R C7R 104.2(5) . . ? C2R C1R C6R 102.0(6) . . ? C7R C1R C6R 99.4(5) . . ? C3R C2R C1R 108.7(6) . . ? C2R C3R C4R 106.6(6) . . ? C3R C4R C5R 102.6(6) . . ? C3R C4R C7R 102.3(6) . . ? C5R C4R C7R 100.2(5) . . ? C6R C5R C4R 102.4(5) . . ? C5R C6R C1R 103.3(5) . . ? C8R C7R C1R 112.8(5) . . ? C8R C7R C4R 114.2(5) . . ? C1R C7R C4R 92.6(4) . . ? O1R C8R C9R 119.4(6) . . ? O1R C8R C7R 121.6(5) . . ? C9R C8R C7R 119.0(6) . . ? C14R C9R C10R 118.0(5) . . ? C14R C9R C8R 124.7(5) . . ? C10R C9R C8R 117.3(6) . . ? C11R C10R C9R 121.0(7) . . ? C10R C11R C12R 120.1(7) . . ? C13R C12R C11R 119.7(6) . . ? C13R C12R C15R 120.0(6) . . ? C11R C12R C15R 120.1(6) . . ? C12R C13R C14R 119.9(5) . . ? C13R C14R C9R 121.2(5) . . ? O2R C15R O3R 122.8(6) . . ? O2R C15R C12R 119.3(5) . . ? O3R C15R C12R 117.8(6) . . ? N1R C16R C23R 108.3(7) . . ? N1R C16R C17R 110.3(7) . . ? C23R C16R C17R 114.2(7) . . ? C22R C17R C18R 110.0(6) . . ? C22R C17R C16R 111.3(6) . . ? C18R C17R C16R 112.2(6) . . ? C17R C18R C19R 112.4(6) . . ? C20R C19R C18R 110.9(6) . . ? C21R C20R C19R 111.5(6) . . ? C20R C21R C22R 113.1(6) . . ? C17R C22R C21R 111.1(7) . . ? C7P C1P C6P 111.6(14) . . ? C7P C1P C2P 101.2(9) . . ? C6P C1P C2P 115.6(12) . . ? O1P C2P C3P 109.3(13) . . ? O1P C2P C1P 104.4(8) . . ? C3P C2P C1P 112.0(10) . . ? C4P C3P C2P 121.8(13) . . ? C3P C4P C5P 125.1(13) . . ? C4P C5P C6P 113.1(11) . . ? C5P C6P C1P 115.3(12) . . ? C8P C7P C1P 104.9(9) . . ? C7P C8P O1P 118.0(9) . . ? C7P C8P C9P 124.6(10) . . ? O1P C8P C9P 116.5(9) . . ? C14P C9P C10P 120.9(10) . . ? C14P C9P C8P 118.9(10) . . ? C10P C9P C8P 120.2(11) . . ? C11P C10P C9P 119.7(11) . . ? C10P C11P C12P 119.2(11) . . ? C13P C12P C11P 120.1(11) . . ? C13P C12P C15P 119.0(12) . . ? C11P C12P C15P 120.5(11) . . ? C14P C13P C12P 120.6(12) . . ? C13P C14P C9P 118.7(12) . . ? O2P C15P O3P 124.5(14) . . ? O2P C15P C12P 117.5(13) . . ? O3P C15P C12P 117.7(12) . . ? N1P C16P C23P 107.3(14) . . ? N1P C16P C17P 110.8(14) . . ? C23P C16P C17P 116.9(14) . . ? C22P C17P C18P 111.6(14) . . ? C22P C17P C16P 111.4(13) . . ? C18P C17P C16P 112.1(13) . . ? C17P C18P C19P 112.6(13) . . ? C20P C19P C18P 110.7(14) . . ? C21P C20P C19P 110.9(14) . . ? C20P C21P C22P 111.5(14) . . ? C17P C22P C21P 111.6(13) . . ? C8P O1P C2P 103.0(8) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.276 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.056 #===END data_27.2%P _database_code_depnum_ccdc_archive 'CCDC 608922' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1598(9) _cell_length_b 17.563(2) _cell_length_c 19.500(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2109.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.163 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11389 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3683 _reflns_number_gt 2137 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.1885P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3683 _refine_ls_number_parameters 353 _refine_ls_number_restraints 213 _refine_ls_R_factor_all 0.1242 _refine_ls_R_factor_gt 0.0872 _refine_ls_wR_factor_ref 0.2781 _refine_ls_wR_factor_gt 0.2509 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.997 _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 C1R C 0.8354(16) 0.9763(5) 0.4836(4) 0.090(4) Uani 0.728(9) 1 d PD A 1 H1R H 0.8365 1.0320 0.4830 0.108 Uiso 0.728(9) 1 calc PR A 1 C2R C 1.0519(14) 0.9378(7) 0.4824(6) 0.121(3) Uani 0.728(9) 1 d PDU A 1 H2R H 1.1834 0.9601 0.4944 0.145 Uiso 0.728(9) 1 calc PR A 1 C3R C 1.0256(17) 0.8663(7) 0.4613(6) 0.119(6) Uani 0.728(9) 1 d PD A 1 H3R H 1.1338 0.8300 0.4553 0.143 Uiso 0.728(9) 1 calc PR A 1 C4R C 0.7832(15) 0.8557(4) 0.4488(4) 0.112(3) Uani 0.728(9) 1 d PD A 1 H4R H 0.7418 0.8134 0.4187 0.135 Uiso 0.728(9) 1 calc PR A 1 C5R C 0.688(2) 0.8542(5) 0.5229(5) 0.123(4) Uani 0.728(9) 1 d PDU A 1 H5R1 H 0.5347 0.8412 0.5226 0.147 Uiso 0.728(9) 1 calc PR A 1 H5R2 H 0.7651 0.8184 0.5518 0.147 Uiso 0.728(9) 1 calc PR A 1 C6R C 0.724(2) 0.9375(6) 0.5471(4) 0.115(4) Uani 0.728(9) 1 d PDU A 1 H6R1 H 0.8177 0.9393 0.5871 0.138 Uiso 0.728(9) 1 calc PR A 1 H6R2 H 0.5873 0.9621 0.5580 0.138 Uiso 0.728(9) 1 calc PR A 1 C7R C 0.7094(15) 0.9369(5) 0.4257(3) 0.087(2) Uani 0.728(9) 1 d PDU A 1 H7R H 0.5522 0.9439 0.4301 0.104 Uiso 0.728(9) 1 calc PR A 1 C8R C 0.7908(14) 0.9596(5) 0.3560(3) 0.092(3) Uani 0.728(9) 1 d PD A 1 C9R C 0.6858(13) 0.9259(5) 0.2940(3) 0.069(3) Uani 0.728(9) 1 d PD A 1 C10R C 0.8088(17) 0.9236(8) 0.2337(4) 0.085(4) Uani 0.728(9) 1 d PD A 1 H10R H 0.9499 0.9425 0.2338 0.102 Uiso 0.728(9) 1 calc PR A 1 C11R C 0.7244(17) 0.8940(8) 0.1747(4) 0.073(3) Uani 0.728(9) 1 d PDU A 1 H11R H 0.8105 0.8909 0.1356 0.088 Uiso 0.728(9) 1 calc PR A 1 C12R C 0.510(2) 0.8684(11) 0.1725(4) 0.069(6) Uani 0.728(9) 1 d PD A 1 C13R C 0.3872(12) 0.8693(5) 0.2312(3) 0.065(2) Uani 0.728(9) 1 d PDU A 1 H13R H 0.2442 0.8523 0.2304 0.078 Uiso 0.728(9) 1 calc PR A 1 C14R C 0.4778(13) 0.8957(6) 0.2919(3) 0.077(2) Uani 0.728(9) 1 d PDU A 1 H14R H 0.3971 0.8931 0.3322 0.093 Uiso 0.728(9) 1 calc PR A 1 C15R C 0.4197(16) 0.8335(9) 0.1079(5) 0.064(4) Uani 0.728(9) 1 d PD A 1 C16R C 0.7795(18) 0.6532(7) 0.1011(4) 0.071(3) Uani 0.728(9) 1 d PDU A 1 H16R H 0.8788 0.6098 0.0982 0.086 Uiso 0.728(9) 1 calc PR A 1 C17R C 0.7357(16) 0.6700(5) 0.1771(4) 0.064(2) Uani 0.728(9) 1 d PD A 1 H17R H 0.6392 0.7143 0.1796 0.076 Uiso 0.728(9) 1 calc PR A 1 C18R C 0.9444(19) 0.6898(8) 0.2154(4) 0.084(3) Uani 0.728(9) 1 d PD A 1 H18A H 1.0079 0.7351 0.1952 0.100 Uiso 0.728(9) 1 calc PR A 1 H18B H 1.0474 0.6484 0.2100 0.100 Uiso 0.728(9) 1 calc PR A 1 C19R C 0.905(2) 0.7037(7) 0.2919(4) 0.102(3) Uani 0.728(9) 1 d PD A 1 H19A H 1.0435 0.7112 0.3148 0.123 Uiso 0.728(9) 1 calc PR A 1 H19B H 0.8202 0.7498 0.2977 0.123 Uiso 0.728(9) 1 calc PR A 1 C20R C 0.7867(19) 0.6374(8) 0.3250(4) 0.119(4) Uani 0.728(9) 1 d PDU A 1 H20A H 0.8810 0.5932 0.3257 0.143 Uiso 0.728(9) 1 calc PR A 1 H20B H 0.7508 0.6503 0.3720 0.143 Uiso 0.728(9) 1 calc PR A 1 C21R C 0.5828(19) 0.6185(10) 0.2866(4) 0.132(5) Uani 0.728(9) 1 d PD A 1 H21A H 0.4815 0.6605 0.2913 0.159 Uiso 0.728(9) 1 calc PR A 1 H21B H 0.5167 0.5739 0.3072 0.159 Uiso 0.728(9) 1 calc PR A 1 C22R C 0.6204(19) 0.6033(7) 0.2107(5) 0.092(3) Uani 0.728(9) 1 d PD A 1 H22A H 0.7074 0.5576 0.2054 0.110 Uiso 0.728(9) 1 calc PR A 1 H22B H 0.4821 0.5949 0.1882 0.110 Uiso 0.728(9) 1 calc PR A 1 C23R C 0.5734(19) 0.6336(7) 0.0610(6) 0.089(3) Uani 0.728(9) 1 d PD A 1 H23A H 0.6108 0.6216 0.0144 0.134 Uiso 0.728(9) 1 calc PR A 1 H23B H 0.4765 0.6764 0.0615 0.134 Uiso 0.728(9) 1 calc PR A 1 H23C H 0.5035 0.5906 0.0818 0.134 Uiso 0.728(9) 1 calc PR A 1 O1R O 0.9441(14) 1.0027(5) 0.3489(4) 0.153(4) Uani 0.728(9) 1 d PD A 1 O2R O 0.2289(14) 0.8112(8) 0.1069(5) 0.089(3) Uani 0.728(9) 1 d PD A 1 O3R O 0.5436(16) 0.8335(9) 0.0557(4) 0.070(3) Uani 0.728(9) 1 d PDU A 1 N1R N 0.8856(17) 0.7201(6) 0.0674(5) 0.062(2) Uani 0.728(9) 1 d PDU A 1 H1R1 H 0.9073 0.7099 0.0232 0.092 Uiso 0.728(9) 1 calc PR A 1 H1R2 H 1.0124 0.7293 0.0876 0.092 Uiso 0.728(9) 1 calc PR A 1 H1R3 H 0.8002 0.7607 0.0713 0.092 Uiso 0.728(9) 1 calc PR A 1 C1P C 0.787(3) 0.9712(12) 0.4747(8) 0.085(11) Uiso 0.272(9) 1 d PD A 2 H1P H 0.7794 1.0270 0.4748 0.103 Uiso 0.272(9) 1 calc PR A 2 C2P C 1.007(2) 0.9449(11) 0.4440(7) 0.091(6) Uiso 0.272(9) 1 d PDU A 2 H2P H 1.1206 0.9819 0.4547 0.109 Uiso 0.272(9) 1 calc PR A 2 C3P C 1.072(4) 0.8669(16) 0.4684(16) 0.136(19) Uiso 0.272(9) 1 d PD A 2 H3P H 1.2045 0.8470 0.4547 0.163 Uiso 0.272(9) 1 calc PR A 2 C4P C 0.945(3) 0.8259(10) 0.5089(11) 0.098(7) Uiso 0.272(9) 1 d PD A 2 H4P H 0.9656 0.7734 0.5086 0.117 Uiso 0.272(9) 1 calc PR A 2 C5P C 0.773(4) 0.8561(13) 0.5548(14) 0.124(8) Uiso 0.272(9) 1 d PDU A 2 H5P1 H 0.8126 0.8458 0.6020 0.149 Uiso 0.272(9) 1 calc PR A 2 H5P2 H 0.6381 0.8297 0.5453 0.149 Uiso 0.272(9) 1 calc PR A 2 C6P C 0.738(6) 0.9408(14) 0.5460(9) 0.129(9) Uiso 0.272(9) 1 d PDU A 2 H6P1 H 0.8289 0.9675 0.5787 0.155 Uiso 0.272(9) 1 calc PR A 2 H6P2 H 0.5881 0.9525 0.5571 0.155 Uiso 0.272(9) 1 calc PR A 2 C7P C 0.630(3) 0.940(2) 0.4227(9) 0.102(8) Uiso 0.272(9) 1 d PDU A 2 H7P H 0.4861 0.9260 0.4295 0.122 Uiso 0.272(9) 1 calc PR A 2 C8P C 0.744(2) 0.9358(11) 0.3649(7) 0.056(6) Uiso 0.272(9) 1 d PD A 2 C9P C 0.656(3) 0.9114(9) 0.2955(8) 0.069(9) Uiso 0.272(9) 1 d PD A 2 C10P C 0.767(4) 0.9313(16) 0.2355(9) 0.053(8) Uiso 0.272(9) 1 d PD A 2 H10P H 0.8930 0.9605 0.2380 0.064 Uiso 0.272(9) 1 calc PR A 2 C11P C 0.689(4) 0.9072(18) 0.1728(9) 0.048(6) Uiso 0.272(9) 1 d PDU A 2 H11P H 0.7674 0.9170 0.1330 0.058 Uiso 0.272(9) 1 calc PR A 2 C12P C 0.492(5) 0.868(2) 0.1692(9) 0.054(13) Uiso 0.272(9) 1 d PD A 2 C13P C 0.395(4) 0.8430(14) 0.2293(9) 0.076(7) Uiso 0.272(9) 1 d PDU A 2 H13P H 0.2861 0.8064 0.2276 0.091 Uiso 0.272(9) 1 calc PR A 2 C14P C 0.460(4) 0.8725(17) 0.2918(9) 0.093(8) Uiso 0.272(9) 1 d PDU A 2 H14P H 0.3740 0.8663 0.3307 0.112 Uiso 0.272(9) 1 calc PR A 2 C15P C 0.398(4) 0.844(2) 0.1007(10) 0.065(14) Uiso 0.272(9) 1 d PD A 2 C16P C 0.806(5) 0.6614(16) 0.1056(11) 0.065(7) Uiso 0.272(9) 1 d PDU A 2 H16P H 0.9352 0.6291 0.1014 0.078 Uiso 0.272(9) 1 calc PR A 2 C17P C 0.781(5) 0.6804(18) 0.1819(11) 0.084(12) Uiso 0.272(9) 1 d PD A 2 H17P H 0.6999 0.7283 0.1846 0.101 Uiso 0.272(9) 1 calc PR A 2 C18P C 1.000(5) 0.694(3) 0.2170(14) 0.107(14) Uiso 0.272(9) 1 d PD A 2 H18C H 1.0766 0.7341 0.1932 0.128 Uiso 0.272(9) 1 calc PR A 2 H18D H 1.0863 0.6478 0.2139 0.128 Uiso 0.272(9) 1 calc PR A 2 C19P C 0.973(6) 0.716(2) 0.2928(15) 0.115(14) Uiso 0.272(9) 1 d PD A 2 H19C H 1.1144 0.7183 0.3143 0.139 Uiso 0.272(9) 1 calc PR A 2 H19D H 0.9076 0.7661 0.2957 0.139 Uiso 0.272(9) 1 calc PR A 2 C20P C 0.832(6) 0.660(3) 0.3311(13) 0.143(10) Uiso 0.272(9) 1 d PDU A 2 H20C H 0.9107 0.6120 0.3359 0.171 Uiso 0.272(9) 1 calc PR A 2 H20D H 0.8037 0.6791 0.3768 0.171 Uiso 0.272(9) 1 calc PR A 2 C21P C 0.619(5) 0.644(2) 0.2956(14) 0.127(15) Uiso 0.272(9) 1 d PD A 2 H21C H 0.5303 0.6900 0.2975 0.152 Uiso 0.272(9) 1 calc PR A 2 H21D H 0.5424 0.6044 0.3199 0.152 Uiso 0.272(9) 1 calc PR A 2 C22P C 0.649(5) 0.621(2) 0.2204(13) 0.095(13) Uiso 0.272(9) 1 d PD A 2 H22C H 0.7223 0.5720 0.2183 0.114 Uiso 0.272(9) 1 calc PR A 2 H22D H 0.5076 0.6151 0.1989 0.114 Uiso 0.272(9) 1 calc PR A 2 C23P C 0.621(5) 0.6187(17) 0.0716(15) 0.077(10) Uiso 0.272(9) 1 d PD A 2 H23D H 0.6602 0.6060 0.0254 0.115 Uiso 0.272(9) 1 calc PR A 2 H23E H 0.4934 0.6503 0.0711 0.115 Uiso 0.272(9) 1 calc PR A 2 H23F H 0.5909 0.5729 0.0968 0.115 Uiso 0.272(9) 1 calc PR A 2 O1P O 0.9676(18) 0.9423(9) 0.3693(6) 0.078(4) Uiso 0.272(9) 1 d PD A 2 O2P O 0.199(4) 0.8317(19) 0.0980(15) 0.088(10) Uiso 0.272(9) 1 d PD A 2 O3P O 0.529(6) 0.819(3) 0.0552(17) 0.094(13) Uiso 0.272(9) 1 d PDU A 2 N1P N 0.850(6) 0.7321(17) 0.0643(15) 0.061(7) Uiso 0.272(9) 1 d PDU A 2 H1P1 H 0.9434 0.7616 0.0867 0.091 Uiso 0.272(9) 1 calc PR A 2 H1P2 H 0.7261 0.7573 0.0579 0.091 Uiso 0.272(9) 1 calc PR A 2 H1P3 H 0.9056 0.7192 0.0238 0.091 Uiso 0.272(9) 1 calc PR A 2 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 C1R 0.107(7) 0.090(6) 0.073(5) -0.011(4) -0.034(5) -0.006(5) C2R 0.101(6) 0.130(8) 0.131(9) 0.023(7) -0.001(6) -0.004(6) C3R 0.113(8) 0.147(12) 0.098(8) 0.000(7) -0.003(6) 0.010(8) C4R 0.152(8) 0.091(6) 0.095(6) -0.007(4) 0.002(6) -0.003(6) C5R 0.167(8) 0.117(7) 0.084(6) 0.020(5) 0.014(6) -0.013(7) C6R 0.144(8) 0.137(8) 0.064(5) -0.018(5) -0.002(5) 0.005(6) C7R 0.103(6) 0.092(5) 0.065(4) -0.025(4) 0.003(4) -0.014(6) C8R 0.104(7) 0.078(6) 0.096(6) 0.011(4) -0.008(5) -0.014(5) C9R 0.081(5) 0.061(4) 0.066(5) -0.012(3) -0.012(3) -0.007(4) C10R 0.059(5) 0.118(9) 0.079(6) -0.021(4) -0.015(4) -0.002(6) C11R 0.073(5) 0.081(7) 0.066(5) -0.009(4) -0.010(4) 0.002(5) C12R 0.065(7) 0.070(7) 0.071(7) -0.009(3) 0.001(3) 0.000(4) C13R 0.069(4) 0.063(5) 0.063(4) -0.023(3) 0.011(3) -0.009(4) C14R 0.096(6) 0.069(5) 0.067(4) -0.018(3) 0.029(4) -0.011(4) C15R 0.067(6) 0.071(6) 0.053(5) -0.011(4) -0.013(4) 0.016(4) C16R 0.083(6) 0.065(5) 0.066(4) 0.001(3) -0.005(4) -0.010(4) C17R 0.070(5) 0.061(4) 0.060(4) 0.004(3) 0.002(3) -0.004(4) C18R 0.088(6) 0.114(7) 0.049(4) 0.009(3) -0.006(4) -0.031(5) C19R 0.118(8) 0.141(10) 0.048(4) -0.001(5) -0.001(5) -0.030(7) C20R 0.157(9) 0.149(10) 0.052(4) 0.033(5) -0.007(5) -0.019(7) C21R 0.140(9) 0.183(14) 0.074(6) 0.039(7) 0.011(6) -0.051(9) C22R 0.099(7) 0.104(8) 0.072(5) 0.006(5) 0.003(4) -0.037(6) C23R 0.097(7) 0.080(6) 0.090(6) 0.006(5) -0.028(5) -0.019(5) O1R 0.199(8) 0.158(8) 0.102(5) -0.024(5) -0.018(5) -0.092(7) O2R 0.073(4) 0.120(8) 0.074(4) -0.012(5) -0.017(3) -0.025(5) O3R 0.072(4) 0.082(7) 0.056(4) -0.015(3) -0.011(2) 0.003(3) N1R 0.053(4) 0.082(5) 0.050(3) -0.011(3) -0.002(3) 0.007(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 C1R C2R 1.496(8) . ? C1R C7R 1.535(8) . ? C1R C6R 1.571(8) . ? C2R C3R 1.331(9) . ? C3R C4R 1.524(9) . ? C4R C5R 1.561(8) . ? C4R C7R 1.563(8) . ? C5R C6R 1.554(9) . ? C7R C8R 1.501(7) . ? C8R O1R 1.218(8) . ? C8R C9R 1.494(7) . ? C9R C14R 1.387(8) . ? C9R C10R 1.400(8) . ? C10R C11R 1.365(7) . ? C11R C12R 1.398(8) . ? C12R C13R 1.371(7) . ? C12R C15R 1.507(7) . ? C13R C14R 1.388(7) . ? C15R O2R 1.240(7) . ? C15R O3R 1.271(7) . ? C16R N1R 1.495(7) . ? C16R C23R 1.530(8) . ? C16R C17R 1.536(7) . ? C17R C22R 1.518(8) . ? C17R C18R 1.526(8) . ? C18R C19R 1.533(7) . ? C19R C20R 1.519(9) . ? C20R C21R 1.499(9) . ? C21R C22R 1.522(9) . ? C1P C7P 1.505(10) . ? C1P C6P 1.519(9) . ? C1P C2P 1.551(9) . ? C2P O1P 1.477(9) . ? C2P C3P 1.504(10) . ? C3P C4P 1.323(10) . ? C4P C5P 1.483(10) . ? C5P C6P 1.513(10) . ? C7P C8P 1.328(9) . ? C8P O1P 1.385(9) . ? C8P C9P 1.521(8) . ? C9P C14P 1.388(9) . ? C9P C10P 1.401(9) . ? C10P C11P 1.382(9) . ? C11P C12P 1.396(9) . ? C12P C13P 1.388(9) . ? C12P C15P 1.518(9) . ? C13P C14P 1.384(9) . ? C15P O2P 1.246(9) . ? C15P O3P 1.272(10) . ? C16P N1P 1.504(10) . ? C16P C23P 1.519(10) . ? C16P C17P 1.533(10) . ? C17P C22P 1.525(10) . ? C17P C18P 1.529(10) . ? C18P C19P 1.537(10) . ? C19P C20P 1.511(10) . ? C20P C21P 1.509(10) . ? C21P C22P 1.535(10) . ? 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 C2R C1R C7R 103.6(6) . . ? C2R C1R C6R 101.9(7) . . ? C7R C1R C6R 99.5(6) . . ? C3R C2R C1R 108.8(7) . . ? C2R C3R C4R 106.5(8) . . ? C3R C4R C5R 102.9(7) . . ? C3R C4R C7R 102.7(7) . . ? C5R C4R C7R 100.0(6) . . ? C6R C5R C4R 102.2(5) . . ? C5R C6R C1R 103.4(5) . . ? C8R C7R C1R 112.1(6) . . ? C8R C7R C4R 114.0(6) . . ? C1R C7R C4R 92.9(5) . . ? O1R C8R C9R 119.3(6) . . ? O1R C8R C7R 121.8(7) . . ? C9R C8R C7R 118.8(6) . . ? C14R C9R C10R 117.7(6) . . ? C14R C9R C8R 125.1(6) . . ? C10R C9R C8R 117.2(7) . . ? C11R C10R C9R 120.8(7) . . ? C10R C11R C12R 120.6(7) . . ? C13R C12R C11R 119.4(6) . . ? C13R C12R C15R 120.1(6) . . ? C11R C12R C15R 120.3(6) . . ? C12R C13R C14R 119.6(6) . . ? C9R C14R C13R 121.6(6) . . ? O2R C15R O3R 123.8(7) . . ? O2R C15R C12R 119.3(6) . . ? O3R C15R C12R 116.7(6) . . ? N1R C16R C23R 108.4(6) . . ? N1R C16R C17R 110.5(7) . . ? C23R C16R C17R 113.0(7) . . ? C22R C17R C18R 111.0(6) . . ? C22R C17R C16R 110.5(6) . . ? C18R C17R C16R 111.6(6) . . ? C17R C18R C19R 112.3(7) . . ? C20R C19R C18R 111.5(7) . . ? C21R C20R C19R 111.1(7) . . ? C20R C21R C22R 113.4(8) . . ? C17R C22R C21R 110.8(8) . . ? C7P C1P C6P 111.2(13) . . ? C7P C1P C2P 100.9(9) . . ? C6P C1P C2P 114.9(12) . . ? O1P C2P C3P 109.1(13) . . ? O1P C2P C1P 104.4(8) . . ? C3P C2P C1P 112.4(10) . . ? C4P C3P C2P 121.9(13) . . ? C3P C4P C5P 125.8(13) . . ? C4P C5P C6P 112.7(11) . . ? C5P C6P C1P 114.9(12) . . ? C8P C7P C1P 104.7(10) . . ? C7P C8P O1P 117.9(9) . . ? C7P C8P C9P 125.5(10) . . ? O1P C8P C9P 115.8(9) . . ? C14P C9P C10P 120.5(10) . . ? C14P C9P C8P 119.7(11) . . ? C10P C9P C8P 119.8(11) . . ? C11P C10P C9P 119.4(11) . . ? C10P C11P C12P 119.9(11) . . ? C13P C12P C11P 119.2(11) . . ? C13P C12P C15P 119.3(12) . . ? C11P C12P C15P 121.0(11) . . ? C14P C13P C12P 120.1(12) . . ? C13P C14P C9P 118.7(12) . . ? O2P C15P O3P 122.6(16) . . ? O2P C15P C12P 117.4(13) . . ? O3P C15P C12P 117.8(15) . . ? N1P C16P C23P 107.9(14) . . ? N1P C16P C17P 111.0(14) . . ? C23P C16P C17P 117.0(14) . . ? C22P C17P C18P 110.9(14) . . ? C22P C17P C16P 112.5(13) . . ? C18P C17P C16P 112.2(14) . . ? C17P C18P C19P 112.0(14) . . ? C20P C19P C18P 111.9(14) . . ? C21P C20P C19P 112.7(14) . . ? C20P C21P C22P 112.5(15) . . ? C17P C22P C21P 110.4(13) . . ? C8P O1P C2P 103.0(8) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.287 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.067 #===END data_27.5%P _database_code_depnum_ccdc_archive 'CCDC 608923' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1549(9) _cell_length_b 17.572(2) _cell_length_c 19.491(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2108.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9775 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11374 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0464 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3679 _reflns_number_gt 2192 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.1713P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.019(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3679 _refine_ls_number_parameters 354 _refine_ls_number_restraints 207 _refine_ls_R_factor_all 0.1156 _refine_ls_R_factor_gt 0.0800 _refine_ls_wR_factor_ref 0.2584 _refine_ls_wR_factor_gt 0.2320 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.023 _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 C1R C 0.8365(13) 0.9760(4) 0.4837(3) 0.084(3) Uani 0.725(8) 1 d PDU A 1 H1R H 0.8390 1.0317 0.4831 0.100 Uiso 0.725(8) 1 calc PR A 1 C2R C 1.0524(12) 0.9373(6) 0.4840(5) 0.116(3) Uani 0.725(8) 1 d PD A 1 H2R H 1.1833 0.9591 0.4974 0.140 Uiso 0.725(8) 1 calc PR A 1 C3R C 1.0258(16) 0.8664(6) 0.4619(6) 0.114(5) Uani 0.725(8) 1 d PD A 1 H3R H 1.1342 0.8302 0.4557 0.137 Uiso 0.725(8) 1 calc PR A 1 C4R C 0.7835(13) 0.8558(4) 0.4486(4) 0.107(3) Uani 0.725(8) 1 d PD A 1 H4R H 0.7429 0.8136 0.4183 0.128 Uiso 0.725(8) 1 calc PR A 1 C5R C 0.684(2) 0.8547(5) 0.5218(4) 0.122(3) Uani 0.725(8) 1 d PD A 1 H5R1 H 0.7585 0.8184 0.5511 0.146 Uiso 0.725(8) 1 calc PR A 1 H5R2 H 0.5305 0.8423 0.5205 0.146 Uiso 0.725(8) 1 calc PR A 1 C6R C 0.721(2) 0.9380(6) 0.5469(4) 0.115(4) Uani 0.725(8) 1 d PDU A 1 H6R1 H 0.8136 0.9393 0.5872 0.138 Uiso 0.725(8) 1 calc PR A 1 H6R2 H 0.5848 0.9630 0.5573 0.138 Uiso 0.725(8) 1 calc PR A 1 C7R C 0.7101(14) 0.9373(4) 0.4255(3) 0.082(2) Uani 0.725(8) 1 d PDU A 1 H7R H 0.5529 0.9444 0.4301 0.099 Uiso 0.725(8) 1 calc PR A 1 C8R C 0.7903(13) 0.9597(4) 0.3561(3) 0.089(2) Uani 0.725(8) 1 d PD A 1 C9R C 0.6864(12) 0.9260(4) 0.2937(3) 0.063(3) Uani 0.725(8) 1 d PD A 1 C10R C 0.8079(17) 0.9243(8) 0.2335(4) 0.084(4) Uani 0.725(8) 1 d PD A 1 H10R H 0.9484 0.9437 0.2333 0.100 Uiso 0.725(8) 1 calc PR A 1 C11R C 0.7228(17) 0.8941(7) 0.1743(4) 0.073(3) Uani 0.725(8) 1 d PDU A 1 H11R H 0.8085 0.8909 0.1351 0.087 Uiso 0.725(8) 1 calc PR A 1 C12R C 0.509(2) 0.8682(10) 0.1725(4) 0.062(6) Uani 0.725(8) 1 d PD A 1 C13R C 0.3876(12) 0.8700(5) 0.2317(3) 0.068(2) Uani 0.725(8) 1 d PDU A 1 H13R H 0.2444 0.8531 0.2311 0.082 Uiso 0.725(8) 1 calc PR A 1 C14R C 0.4768(12) 0.8966(6) 0.2921(3) 0.072(3) Uani 0.725(8) 1 d PD A 1 H14R H 0.3955 0.8948 0.3323 0.087 Uiso 0.725(8) 1 calc PR A 1 C15R C 0.4171(14) 0.8336(9) 0.1077(5) 0.063(4) Uani 0.725(8) 1 d PD A 1 C16R C 0.7752(19) 0.6547(8) 0.1015(4) 0.075(3) Uani 0.725(8) 1 d PDU A 1 H16R H 0.8766 0.6118 0.0983 0.090 Uiso 0.725(8) 1 calc PR A 1 C17R C 0.7340(17) 0.6702(6) 0.1772(4) 0.065(3) Uani 0.725(8) 1 d PD A 1 H17R H 0.6373 0.7144 0.1805 0.078 Uiso 0.725(8) 1 calc PR A 1 C18R C 0.9434(16) 0.6890(7) 0.2159(4) 0.086(3) Uani 0.725(8) 1 d PDU A 1 H18A H 1.0446 0.6470 0.2110 0.103 Uiso 0.725(8) 1 calc PR A 1 H18B H 1.0097 0.7338 0.1957 0.103 Uiso 0.725(8) 1 calc PR A 1 C19R C 0.9029(19) 0.7035(6) 0.2920(3) 0.101(3) Uani 0.725(8) 1 d PD A 1 H19A H 1.0406 0.7111 0.3152 0.121 Uiso 0.725(8) 1 calc PR A 1 H19B H 0.8172 0.7495 0.2974 0.121 Uiso 0.725(8) 1 calc PR A 1 C20R C 0.7833(17) 0.6367(6) 0.3248(4) 0.115(3) Uani 0.725(8) 1 d PDU A 1 H20A H 0.8782 0.5927 0.3257 0.138 Uiso 0.725(8) 1 calc PR A 1 H20B H 0.7466 0.6495 0.3719 0.138 Uiso 0.725(8) 1 calc PR A 1 C21R C 0.5808(17) 0.6175(8) 0.2865(4) 0.120(4) Uani 0.725(8) 1 d PDU A 1 H21A H 0.4783 0.6591 0.2913 0.144 Uiso 0.725(8) 1 calc PR A 1 H21B H 0.5157 0.5726 0.3070 0.144 Uiso 0.725(8) 1 calc PR A 1 C22R C 0.619(2) 0.6026(7) 0.2103(5) 0.102(4) Uani 0.725(8) 1 d PD A 1 H22A H 0.7078 0.5573 0.2049 0.122 Uiso 0.725(8) 1 calc PR A 1 H22B H 0.4815 0.5939 0.1876 0.122 Uiso 0.725(8) 1 calc PR A 1 C23R C 0.571(2) 0.6338(8) 0.0618(6) 0.089(3) Uani 0.725(8) 1 d PD A 1 H23A H 0.6092 0.6218 0.0153 0.133 Uiso 0.725(8) 1 calc PR A 1 H23B H 0.4723 0.6760 0.0623 0.133 Uiso 0.725(8) 1 calc PR A 1 H23C H 0.5036 0.5905 0.0828 0.133 Uiso 0.725(8) 1 calc PR A 1 O1R O 0.9432(13) 1.0032(5) 0.3489(3) 0.143(3) Uani 0.725(8) 1 d PDU A 1 O2R O 0.2253(13) 0.8127(8) 0.1078(5) 0.092(3) Uani 0.725(8) 1 d PD A 1 O3R O 0.539(2) 0.8303(11) 0.0560(6) 0.087(7) Uani 0.725(8) 1 d PD A 1 N1R N 0.879(3) 0.7218(11) 0.0681(6) 0.070(5) Uani 0.725(8) 1 d PD A 1 H1R1 H 0.9009 0.7119 0.0239 0.104 Uiso 0.725(8) 1 calc PR A 1 H1R2 H 1.0056 0.7315 0.0883 0.104 Uiso 0.725(8) 1 calc PR A 1 H1R3 H 0.7922 0.7621 0.0722 0.104 Uiso 0.725(8) 1 calc PR A 1 C1P C 0.780(3) 0.9700(12) 0.4759(8) 0.090(7) Uiso 0.275(8) 1 d PDU A 2 H1P H 0.7713 1.0256 0.4771 0.108 Uiso 0.275(8) 1 calc PR A 2 C2P C 1.003(2) 0.9464(10) 0.4459(6) 0.084(6) Uiso 0.275(8) 1 d PD A 2 H2P H 1.1138 0.9846 0.4569 0.101 Uiso 0.275(8) 1 calc PR A 2 C3P C 1.073(4) 0.8689(16) 0.4709(16) 0.15(2) Uiso 0.275(8) 1 d PD A 2 H3P H 1.2101 0.8509 0.4592 0.182 Uiso 0.275(8) 1 calc PR A 2 C4P C 0.944(3) 0.8260(10) 0.5092(11) 0.097(6) Uiso 0.275(8) 1 d PD A 2 H4P H 0.9641 0.7736 0.5070 0.116 Uiso 0.275(8) 1 calc PR A 2 C5P C 0.770(5) 0.8547(13) 0.5554(16) 0.147(13) Uiso 0.275(8) 1 d PD A 2 H5P1 H 0.8110 0.8448 0.6026 0.176 Uiso 0.275(8) 1 calc PR A 2 H5P2 H 0.6368 0.8272 0.5461 0.176 Uiso 0.275(8) 1 calc PR A 2 C6P C 0.729(5) 0.9391(14) 0.5467(9) 0.128(9) Uiso 0.275(8) 1 d PDU A 2 H6P1 H 0.8157 0.9665 0.5801 0.154 Uiso 0.275(8) 1 calc PR A 2 H6P2 H 0.5774 0.9492 0.5568 0.154 Uiso 0.275(8) 1 calc PR A 2 C7P C 0.627(3) 0.9405(18) 0.4222(9) 0.098(8) Uiso 0.275(8) 1 d PDU A 2 H7P H 0.4808 0.9285 0.4276 0.117 Uiso 0.275(8) 1 calc PR A 2 C8P C 0.745(2) 0.9354(12) 0.3655(7) 0.065(6) Uiso 0.275(8) 1 d PD A 2 C9P C 0.657(3) 0.9118(9) 0.2956(7) 0.073(10) Uiso 0.275(8) 1 d PD A 2 C10P C 0.769(4) 0.9315(16) 0.2359(9) 0.054(7) Uiso 0.275(8) 1 d PD A 2 H10P H 0.8958 0.9604 0.2385 0.065 Uiso 0.275(8) 1 calc PR A 2 C11P C 0.691(4) 0.9077(17) 0.1728(9) 0.045(6) Uiso 0.275(8) 1 d PDU A 2 H11P H 0.7720 0.9160 0.1332 0.054 Uiso 0.275(8) 1 calc PR A 2 C12P C 0.490(5) 0.871(3) 0.1693(9) 0.061(16) Uiso 0.275(8) 1 d PD A 2 C13P C 0.391(4) 0.8467(14) 0.2293(9) 0.075(5) Uiso 0.275(8) 1 d PDU A 2 H13P H 0.2754 0.8127 0.2271 0.090 Uiso 0.275(8) 1 calc PR A 2 C14P C 0.462(3) 0.8724(16) 0.2922(9) 0.094(12) Uiso 0.275(8) 1 d PD A 2 H14P H 0.3809 0.8635 0.3316 0.112 Uiso 0.275(8) 1 calc PR A 2 C15P C 0.403(4) 0.845(2) 0.1000(10) 0.071(15) Uiso 0.275(8) 1 d PD A 2 C16P C 0.809(5) 0.6571(19) 0.1026(10) 0.063(7) Uiso 0.275(8) 1 d PDU A 2 H16P H 0.9330 0.6220 0.1011 0.075 Uiso 0.275(8) 1 calc PR A 2 C17P C 0.776(4) 0.6797(18) 0.1776(11) 0.075(10) Uiso 0.275(8) 1 d PD A 2 H17P H 0.6925 0.7273 0.1778 0.090 Uiso 0.275(8) 1 calc PR A 2 C18P C 0.993(4) 0.696(2) 0.2131(13) 0.098(8) Uiso 0.275(8) 1 d PDU A 2 H18C H 1.0673 0.7364 0.1885 0.117 Uiso 0.275(8) 1 calc PR A 2 H18D H 1.0828 0.6509 0.2111 0.117 Uiso 0.275(8) 1 calc PR A 2 C19P C 0.963(4) 0.7200(17) 0.2883(13) 0.095(9) Uiso 0.275(8) 1 d PD A 2 H19C H 1.1048 0.7251 0.3098 0.114 Uiso 0.275(8) 1 calc PR A 2 H19D H 0.8919 0.7691 0.2901 0.114 Uiso 0.275(8) 1 calc PR A 2 C20P C 0.830(5) 0.6621(19) 0.3272(12) 0.124(6) Uiso 0.275(8) 1 d PDU A 2 H20C H 0.9120 0.6152 0.3312 0.149 Uiso 0.275(8) 1 calc PR A 2 H20D H 0.8025 0.6810 0.3732 0.149 Uiso 0.275(8) 1 calc PR A 2 C21P C 0.615(4) 0.6456(19) 0.2925(12) 0.118(9) Uiso 0.275(8) 1 d PDU A 2 H21C H 0.5251 0.6907 0.2944 0.142 Uiso 0.275(8) 1 calc PR A 2 H21D H 0.5413 0.6054 0.3174 0.142 Uiso 0.275(8) 1 calc PR A 2 C22P C 0.643(4) 0.6213(17) 0.2174(12) 0.077(8) Uiso 0.275(8) 1 d PD A 2 H22C H 0.7157 0.5723 0.2156 0.093 Uiso 0.275(8) 1 calc PR A 2 H22D H 0.5014 0.6157 0.1963 0.093 Uiso 0.275(8) 1 calc PR A 2 C23P C 0.621(5) 0.6181(18) 0.0666(15) 0.075(9) Uiso 0.275(8) 1 d PD A 2 H23D H 0.6622 0.6056 0.0205 0.113 Uiso 0.275(8) 1 calc PR A 2 H23E H 0.4979 0.6517 0.0658 0.113 Uiso 0.275(8) 1 calc PR A 2 H23F H 0.5834 0.5725 0.0909 0.113 Uiso 0.275(8) 1 calc PR A 2 O1P O 0.9675(18) 0.9428(9) 0.3708(6) 0.086(4) Uiso 0.275(8) 1 d PDU A 2 O2P O 0.207(4) 0.829(2) 0.0952(15) 0.094(11) Uiso 0.275(8) 1 d PD A 2 O3P O 0.543(5) 0.8305(19) 0.0542(13) 0.060(12) Uiso 0.275(8) 1 d PD A 2 N1P N 0.871(7) 0.726(2) 0.0617(16) 0.052(10) Uiso 0.275(8) 1 d PD A 2 H1P1 H 0.9649 0.7543 0.0858 0.078 Uiso 0.275(8) 1 calc PR A 2 H1P2 H 0.7531 0.7536 0.0528 0.078 Uiso 0.275(8) 1 calc PR A 2 H1P3 H 0.9331 0.7119 0.0225 0.078 Uiso 0.275(8) 1 calc PR A 2 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 C1R 0.093(5) 0.083(5) 0.075(5) -0.016(3) -0.032(4) -0.006(4) C2R 0.098(6) 0.133(9) 0.117(8) 0.017(7) -0.008(5) 0.007(6) C3R 0.111(7) 0.130(10) 0.101(7) -0.007(6) 0.003(6) 0.021(7) C4R 0.145(7) 0.084(5) 0.091(6) -0.012(4) 0.002(5) 0.000(5) C5R 0.190(9) 0.101(6) 0.075(5) 0.017(4) 0.016(7) -0.008(7) C6R 0.135(7) 0.140(8) 0.070(5) -0.018(5) -0.001(5) 0.003(6) C7R 0.095(5) 0.088(5) 0.063(4) -0.018(3) 0.003(4) -0.013(5) C8R 0.100(6) 0.072(5) 0.095(6) 0.007(4) -0.007(4) -0.014(5) C9R 0.075(4) 0.056(4) 0.058(5) -0.006(3) -0.009(3) -0.005(4) C10R 0.058(4) 0.106(8) 0.087(6) -0.023(4) -0.011(4) -0.003(5) C11R 0.078(5) 0.077(7) 0.064(4) -0.007(3) -0.007(4) 0.004(5) C12R 0.058(6) 0.064(7) 0.063(7) -0.008(3) 0.000(3) 0.002(4) C13R 0.065(3) 0.066(5) 0.073(4) -0.028(3) 0.011(3) -0.009(3) C14R 0.096(6) 0.060(5) 0.061(4) -0.016(3) 0.025(4) -0.012(4) C15R 0.072(7) 0.064(6) 0.054(5) -0.005(4) -0.018(4) 0.010(4) C16R 0.081(6) 0.068(4) 0.077(5) 0.005(3) 0.003(4) -0.009(4) C17R 0.073(5) 0.068(5) 0.054(4) 0.003(3) 0.006(3) -0.003(4) C18R 0.088(5) 0.105(6) 0.065(4) 0.007(3) -0.004(4) -0.037(5) C19R 0.126(8) 0.128(8) 0.047(4) 0.002(4) 0.004(4) -0.043(6) C20R 0.147(7) 0.132(7) 0.066(4) 0.030(4) -0.001(5) -0.019(6) C21R 0.139(7) 0.154(10) 0.067(5) 0.025(5) 0.014(5) -0.041(7) C22R 0.109(7) 0.101(8) 0.095(6) 0.011(6) 0.009(5) -0.040(6) C23R 0.096(7) 0.080(6) 0.091(6) 0.001(5) -0.026(5) -0.017(6) O1R 0.184(7) 0.153(7) 0.093(4) -0.022(4) -0.014(4) -0.088(6) O2R 0.073(4) 0.129(8) 0.074(4) -0.013(5) -0.016(3) -0.036(4) O3R 0.090(8) 0.119(10) 0.053(5) -0.019(3) -0.010(2) 0.008(3) N1R 0.070(6) 0.097(9) 0.042(4) -0.010(3) -0.002(3) -0.003(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 C1R C2R 1.492(8) . ? C1R C7R 1.535(7) . ? C1R C6R 1.570(8) . ? C2R C3R 1.328(9) . ? C3R C4R 1.525(9) . ? C4R C5R 1.553(8) . ? C4R C7R 1.567(8) . ? C5R C6R 1.560(9) . ? C7R C8R 1.493(7) . ? C8R O1R 1.220(7) . ? C8R C9R 1.497(7) . ? C9R C14R 1.391(8) . ? C9R C10R 1.392(8) . ? C10R C11R 1.373(7) . ? C11R C12R 1.395(7) . ? C12R C13R 1.374(7) . ? C12R C15R 1.512(7) . ? C13R C14R 1.379(7) . ? C15R O2R 1.236(6) . ? C15R O3R 1.257(7) . ? C16R N1R 1.491(8) . ? C16R C23R 1.519(8) . ? C16R C17R 1.521(7) . ? C17R C22R 1.525(8) . ? C17R C18R 1.530(8) . ? C18R C19R 1.526(7) . ? C19R C20R 1.525(8) . ? C20R C21R 1.492(8) . ? C21R C22R 1.527(8) . ? C1P C7P 1.501(10) . ? C1P C6P 1.516(9) . ? C1P C2P 1.549(9) . ? C2P O1P 1.480(9) . ? C2P C3P 1.508(10) . ? C3P C4P 1.325(10) . ? C4P C5P 1.488(10) . ? C5P C6P 1.513(10) . ? C7P C8P 1.326(9) . ? C8P O1P 1.381(9) . ? C8P C9P 1.522(8) . ? C9P C14P 1.388(9) . ? C9P C10P 1.396(9) . ? C10P C11P 1.386(9) . ? C11P C12P 1.398(9) . ? C12P C13P 1.388(10) . ? C12P C15P 1.521(9) . ? C13P C14P 1.378(9) . ? C15P O2P 1.242(9) . ? C15P O3P 1.268(10) . ? C16P N1P 1.502(10) . ? C16P C23P 1.518(10) . ? C16P C17P 1.530(10) . ? C17P C22P 1.524(10) . ? C17P C18P 1.530(10) . ? C18P C19P 1.535(10) . ? C19P C20P 1.513(10) . ? C20P C21P 1.511(10) . ? C21P C22P 1.535(10) . ? 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 C2R C1R C7R 104.6(6) . . ? C2R C1R C6R 101.8(7) . . ? C7R C1R C6R 99.4(6) . . ? C3R C2R C1R 108.5(7) . . ? C2R C3R C4R 106.9(7) . . ? C3R C4R C5R 103.3(7) . . ? C3R C4R C7R 102.7(6) . . ? C5R C4R C7R 99.3(5) . . ? C4R C5R C6R 102.6(5) . . ? C5R C6R C1R 102.7(5) . . ? C8R C7R C1R 112.6(6) . . ? C8R C7R C4R 114.0(6) . . ? C1R C7R C4R 92.6(5) . . ? O1R C8R C7R 121.6(6) . . ? O1R C8R C9R 119.0(6) . . ? C7R C8R C9R 119.4(6) . . ? C14R C9R C10R 118.1(6) . . ? C14R C9R C8R 124.2(6) . . ? C10R C9R C8R 117.7(7) . . ? C11R C10R C9R 120.8(7) . . ? C10R C11R C12R 120.4(7) . . ? C13R C12R C11R 119.0(6) . . ? C13R C12R C15R 120.6(6) . . ? C11R C12R C15R 120.2(6) . . ? C12R C13R C14R 120.5(6) . . ? C13R C14R C9R 121.0(5) . . ? O2R C15R O3R 123.9(8) . . ? O2R C15R C12R 118.3(6) . . ? O3R C15R C12R 117.8(7) . . ? N1R C16R C23R 108.8(7) . . ? N1R C16R C17R 110.7(7) . . ? C23R C16R C17R 113.5(8) . . ? C16R C17R C22R 110.4(6) . . ? C16R C17R C18R 112.1(6) . . ? C22R C17R C18R 110.4(6) . . ? C19R C18R C17R 112.2(7) . . ? C20R C19R C18R 111.0(7) . . ? C21R C20R C19R 111.6(7) . . ? C20R C21R C22R 113.3(7) . . ? C17R C22R C21R 110.5(7) . . ? C7P C1P C6P 112.4(14) . . ? C7P C1P C2P 101.6(9) . . ? C6P C1P C2P 115.6(12) . . ? O1P C2P C3P 108.9(13) . . ? O1P C2P C1P 104.7(8) . . ? C3P C2P C1P 111.8(10) . . ? C4P C3P C2P 121.7(13) . . ? C3P C4P C5P 125.3(14) . . ? C4P C5P C6P 112.7(11) . . ? C5P C6P C1P 114.7(12) . . ? C8P C7P C1P 105.2(9) . . ? C7P C8P O1P 118.2(9) . . ? C7P C8P C9P 124.8(10) . . ? O1P C8P C9P 116.4(9) . . ? C14P C9P C10P 120.8(10) . . ? C14P C9P C8P 119.0(11) . . ? C10P C9P C8P 120.2(11) . . ? C11P C10P C9P 119.5(11) . . ? C10P C11P C12P 119.4(11) . . ? C13P C12P C11P 119.3(11) . . ? C13P C12P C15P 120.1(12) . . ? C11P C12P C15P 119.5(11) . . ? C14P C13P C12P 120.6(12) . . ? C13P C14P C9P 118.8(12) . . ? O2P C15P O3P 123.9(16) . . ? O2P C15P C12P 118.6(13) . . ? O3P C15P C12P 116.5(14) . . ? N1P C16P C23P 108.4(14) . . ? N1P C16P C17P 109.3(14) . . ? C23P C16P C17P 117.0(14) . . ? C22P C17P C18P 111.4(14) . . ? C22P C17P C16P 112.6(13) . . ? C18P C17P C16P 111.2(13) . . ? C17P C18P C19P 112.3(13) . . ? C20P C19P C18P 111.0(14) . . ? C21P C20P C19P 112.3(13) . . ? C20P C21P C22P 112.6(14) . . ? C17P C22P C21P 110.9(13) . . ? C8P O1P C2P 103.1(8) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.280 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.062 #===END data_29.4%P _database_code_depnum_ccdc_archive 'CCDC 608924' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1644(9) _cell_length_b 17.546(3) _cell_length_c 19.520(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2111.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 17 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9594 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11388 _diffrn_reflns_av_R_equivalents 0.0524 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -4 _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 23 _diffrn_reflns_theta_min 3.47 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3686 _reflns_number_gt 2046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3686 _refine_ls_number_parameters 353 _refine_ls_number_restraints 231 _refine_ls_R_factor_all 0.1373 _refine_ls_R_factor_gt 0.0972 _refine_ls_wR_factor_ref 0.3017 _refine_ls_wR_factor_gt 0.2748 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.025 _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 C1R C 0.8370(16) 0.9765(5) 0.4840(4) 0.094(4) Uani 0.706(9) 1 d PD A 1 H1R H 0.8392 1.0324 0.4833 0.112 Uiso 0.706(9) 1 calc PR A 1 C2R C 1.0523(15) 0.9373(7) 0.4834(7) 0.124(4) Uani 0.706(9) 1 d PDU A 1 H2R H 1.1837 0.9594 0.4957 0.149 Uiso 0.706(9) 1 calc PR A 1 C3R C 1.0262(18) 0.8660(7) 0.4624(7) 0.123(6) Uani 0.706(9) 1 d PD A 1 H3R H 1.1343 0.8295 0.4570 0.148 Uiso 0.706(9) 1 calc PR A 1 C4R C 0.7848(17) 0.8555(5) 0.4489(5) 0.123(4) Uani 0.706(9) 1 d PD A 1 H4R H 0.7444 0.8132 0.4187 0.148 Uiso 0.706(9) 1 calc PR A 1 C5R C 0.687(3) 0.8544(6) 0.5222(5) 0.135(5) Uani 0.706(9) 1 d PD A 1 H5R1 H 0.7620 0.8182 0.5514 0.162 Uiso 0.706(9) 1 calc PR A 1 H5R2 H 0.5335 0.8418 0.5212 0.162 Uiso 0.706(9) 1 calc PR A 1 C6R C 0.724(3) 0.9381(7) 0.5469(5) 0.121(4) Uani 0.706(9) 1 d PDU A 1 H6R1 H 0.8164 0.9396 0.5871 0.145 Uiso 0.706(9) 1 calc PR A 1 H6R2 H 0.5872 0.9629 0.5575 0.145 Uiso 0.706(9) 1 calc PR A 1 C7R C 0.7095(17) 0.9369(5) 0.4260(3) 0.092(3) Uani 0.706(9) 1 d PDU A 1 H7R H 0.5524 0.9438 0.4306 0.110 Uiso 0.706(9) 1 calc PR A 1 C8R C 0.7900(15) 0.9592(5) 0.3565(4) 0.098(3) Uani 0.706(9) 1 d PDU A 1 C9R C 0.6862(14) 0.9253(5) 0.2945(4) 0.072(3) Uani 0.706(9) 1 d PD A 1 C10R C 0.8075(17) 0.9234(9) 0.2345(5) 0.084(4) Uani 0.706(9) 1 d PDU A 1 H10R H 0.9475 0.9431 0.2346 0.101 Uiso 0.706(9) 1 calc PR A 1 C11R C 0.7255(18) 0.8930(8) 0.1752(5) 0.077(4) Uani 0.706(9) 1 d PDU A 1 H11R H 0.8132 0.8888 0.1367 0.092 Uiso 0.706(9) 1 calc PR A 1 C12R C 0.510(2) 0.8683(11) 0.1728(5) 0.066(6) Uani 0.706(9) 1 d PD A 1 C13R C 0.3897(14) 0.8680(6) 0.2320(4) 0.071(3) Uani 0.706(9) 1 d PDU A 1 H13R H 0.2489 0.8490 0.2317 0.085 Uiso 0.706(9) 1 calc PR A 1 C14R C 0.4775(14) 0.8960(6) 0.2919(4) 0.079(3) Uani 0.706(9) 1 d PDU A 1 H14R H 0.3945 0.8951 0.3317 0.095 Uiso 0.706(9) 1 calc PR A 1 C15R C 0.4212(16) 0.8332(9) 0.1081(5) 0.065(4) Uani 0.706(9) 1 d PD A 1 C16R C 0.776(2) 0.6554(8) 0.1001(5) 0.076(4) Uani 0.706(9) 1 d PDU A 1 H16R H 0.8793 0.6132 0.0958 0.092 Uiso 0.706(9) 1 calc PR A 1 C17R C 0.7357(19) 0.6696(7) 0.1764(4) 0.070(3) Uani 0.706(9) 1 d PD A 1 H17R H 0.6373 0.7132 0.1804 0.084 Uiso 0.706(9) 1 calc PR A 1 C18R C 0.9438(19) 0.6893(9) 0.2148(4) 0.094(3) Uani 0.706(9) 1 d PDU A 1 H18A H 1.0055 0.7353 0.1953 0.112 Uiso 0.706(9) 1 calc PR A 1 H18B H 1.0478 0.6484 0.2085 0.112 Uiso 0.706(9) 1 calc PR A 1 C19R C 0.908(2) 0.7016(7) 0.2915(4) 0.100(3) Uani 0.706(9) 1 d PDU A 1 H19A H 1.0468 0.7083 0.3140 0.120 Uiso 0.706(9) 1 calc PR A 1 H19B H 0.8236 0.7477 0.2984 0.120 Uiso 0.706(9) 1 calc PR A 1 C20R C 0.790(2) 0.6346(7) 0.3236(5) 0.122(4) Uani 0.706(9) 1 d PDU A 1 H20A H 0.8853 0.5907 0.3243 0.147 Uiso 0.706(9) 1 calc PR A 1 H20B H 0.7529 0.6470 0.3706 0.147 Uiso 0.706(9) 1 calc PR A 1 C21R C 0.5871(19) 0.6146(10) 0.2856(5) 0.124(4) Uani 0.706(9) 1 d PDU A 1 H21A H 0.4829 0.6556 0.2911 0.149 Uiso 0.706(9) 1 calc PR A 1 H21B H 0.5249 0.5690 0.3057 0.149 Uiso 0.706(9) 1 calc PR A 1 C22R C 0.624(2) 0.6009(9) 0.2092(5) 0.101(4) Uani 0.706(9) 1 d PD A 1 H22A H 0.4858 0.5920 0.1869 0.121 Uiso 0.706(9) 1 calc PR A 1 H22B H 0.7131 0.5559 0.2030 0.121 Uiso 0.706(9) 1 calc PR A 1 C23R C 0.571(2) 0.6343(9) 0.0610(7) 0.094(4) Uani 0.706(9) 1 d PD A 1 H23A H 0.6075 0.6222 0.0144 0.140 Uiso 0.706(9) 1 calc PR A 1 H23B H 0.4718 0.6765 0.0616 0.140 Uiso 0.706(9) 1 calc PR A 1 H23C H 0.5040 0.5908 0.0822 0.140 Uiso 0.706(9) 1 calc PR A 1 O1R O 0.9440(16) 1.0026(6) 0.3487(4) 0.155(4) Uani 0.706(9) 1 d PDU A 1 O2R O 0.2306(14) 0.8108(8) 0.1070(5) 0.090(3) Uani 0.706(9) 1 d PD A 1 O3R O 0.5446(15) 0.8348(8) 0.0555(4) 0.068(3) Uani 0.706(9) 1 d PD A 1 N1R N 0.875(3) 0.7246(11) 0.0679(7) 0.080(7) Uani 0.706(9) 1 d PD A 1 H1R1 H 0.8983 0.7158 0.0236 0.119 Uiso 0.706(9) 1 calc PR A 1 H1R2 H 1.0003 0.7352 0.0884 0.119 Uiso 0.706(9) 1 calc PR A 1 H1R3 H 0.7851 0.7640 0.0725 0.119 Uiso 0.706(9) 1 calc PR A 1 C1P C 0.782(3) 0.9696(12) 0.4749(8) 0.082(9) Uiso 0.294(9) 1 d PD A 2 H1P H 0.7710 1.0253 0.4746 0.098 Uiso 0.294(9) 1 calc PR A 2 C2P C 1.004(2) 0.9450(10) 0.4446(7) 0.089(6) Uiso 0.294(9) 1 d PDU A 2 H2P H 1.1154 0.9830 0.4555 0.107 Uiso 0.294(9) 1 calc PR A 2 C3P C 1.073(4) 0.8677(17) 0.4698(17) 0.139(19) Uiso 0.294(9) 1 d PD A 2 H3P H 1.2071 0.8486 0.4565 0.166 Uiso 0.294(9) 1 calc PR A 2 C4P C 0.949(3) 0.8259(10) 0.5104(11) 0.096(7) Uiso 0.294(9) 1 d PD A 2 H4P H 0.9769 0.7739 0.5118 0.115 Uiso 0.294(9) 1 calc PR A 2 C5P C 0.768(5) 0.8544(14) 0.5540(16) 0.137(13) Uiso 0.294(9) 1 d PD A 2 H5P1 H 0.7983 0.8425 0.6015 0.164 Uiso 0.294(9) 1 calc PR A 2 H5P2 H 0.6348 0.8286 0.5412 0.164 Uiso 0.294(9) 1 calc PR A 2 C6P C 0.737(5) 0.9398(14) 0.5465(9) 0.128(9) Uiso 0.294(9) 1 d PDU A 2 H6P1 H 0.5887 0.9525 0.5588 0.153 Uiso 0.294(9) 1 calc PR A 2 H6P2 H 0.8321 0.9656 0.5785 0.153 Uiso 0.294(9) 1 calc PR A 2 C7P C 0.630(3) 0.937(2) 0.4223(9) 0.102(8) Uiso 0.294(9) 1 d PDU A 2 H7P H 0.4870 0.9218 0.4288 0.123 Uiso 0.294(9) 1 calc PR A 2 C8P C 0.744(2) 0.9340(13) 0.3647(7) 0.068(6) Uiso 0.294(9) 1 d PDU A 2 C9P C 0.655(3) 0.9100(10) 0.2954(8) 0.068(9) Uiso 0.294(9) 1 d PD A 2 C10P C 0.768(4) 0.9285(18) 0.2356(9) 0.073(7) Uiso 0.294(9) 1 d PDU A 2 H10P H 0.8975 0.9556 0.2383 0.087 Uiso 0.294(9) 1 calc PR A 2 C11P C 0.687(4) 0.9065(16) 0.1725(9) 0.045(6) Uiso 0.294(9) 1 d PDU A 2 H11P H 0.7651 0.9172 0.1328 0.055 Uiso 0.294(9) 1 calc PR A 2 C12P C 0.490(5) 0.868(2) 0.1684(9) 0.061(13) Uiso 0.294(9) 1 d PD A 2 C13P C 0.384(4) 0.8465(18) 0.2280(10) 0.089(8) Uiso 0.294(9) 1 d PDU A 2 H13P H 0.2625 0.8153 0.2257 0.107 Uiso 0.294(9) 1 calc PR A 2 C14P C 0.459(4) 0.8714(17) 0.2910(10) 0.091(8) Uiso 0.294(9) 1 d PDU A 2 H14P H 0.3779 0.8622 0.3303 0.110 Uiso 0.294(9) 1 calc PR A 2 C15P C 0.397(4) 0.843(2) 0.0998(10) 0.073(15) Uiso 0.294(9) 1 d PD A 2 C16P C 0.810(5) 0.6536(17) 0.1041(11) 0.066(7) Uiso 0.294(9) 1 d PDU A 2 H16P H 0.9289 0.6164 0.1033 0.079 Uiso 0.294(9) 1 calc PR A 2 C17P C 0.777(5) 0.6777(19) 0.1788(11) 0.087(12) Uiso 0.294(9) 1 d PD A 2 H17P H 0.6956 0.7258 0.1783 0.104 Uiso 0.294(9) 1 calc PR A 2 C18P C 0.993(4) 0.693(3) 0.2146(14) 0.109(8) Uiso 0.294(9) 1 d PDU A 2 H18C H 1.0723 0.7317 0.1893 0.131 Uiso 0.294(9) 1 calc PR A 2 H18D H 1.0797 0.6468 0.2142 0.131 Uiso 0.294(9) 1 calc PR A 2 C19P C 0.963(5) 0.7196(18) 0.2890(14) 0.103(5) Uiso 0.294(9) 1 d PDU A 2 H19C H 1.1035 0.7239 0.3110 0.123 Uiso 0.294(9) 1 calc PR A 2 H19D H 0.8957 0.7696 0.2893 0.123 Uiso 0.294(9) 1 calc PR A 2 C20P C 0.823(5) 0.664(2) 0.3289(13) 0.132(6) Uiso 0.294(9) 1 d PDU A 2 H20C H 0.9017 0.6172 0.3354 0.159 Uiso 0.294(9) 1 calc PR A 2 H20D H 0.7928 0.6857 0.3738 0.159 Uiso 0.294(9) 1 calc PR A 2 C21P C 0.610(4) 0.648(2) 0.2932(13) 0.116(9) Uiso 0.294(9) 1 d PDU A 2 H21C H 0.5221 0.6933 0.2930 0.139 Uiso 0.294(9) 1 calc PR A 2 H21D H 0.5329 0.6088 0.3188 0.139 Uiso 0.294(9) 1 calc PR A 2 C22P C 0.642(5) 0.6201(19) 0.2193(13) 0.089(11) Uiso 0.294(9) 1 d PD A 2 H22C H 0.7157 0.5712 0.2194 0.107 Uiso 0.294(9) 1 calc PR A 2 H22D H 0.5022 0.6135 0.1975 0.107 Uiso 0.294(9) 1 calc PR A 2 C23P C 0.617(4) 0.6176(17) 0.0680(15) 0.070(9) Uiso 0.294(9) 1 d PD A 2 H23D H 0.6570 0.6049 0.0219 0.105 Uiso 0.294(9) 1 calc PR A 2 H23E H 0.4988 0.6531 0.0675 0.105 Uiso 0.294(9) 1 calc PR A 2 H23F H 0.5747 0.5723 0.0920 0.105 Uiso 0.294(9) 1 calc PR A 2 O1P O 0.9672(19) 0.9423(9) 0.3700(6) 0.083(4) Uiso 0.294(9) 1 d PDU A 2 O2P O 0.198(4) 0.8318(18) 0.0972(14) 0.091(10) Uiso 0.294(9) 1 d PD A 2 O3P O 0.530(5) 0.816(2) 0.0566(15) 0.088(12) Uiso 0.294(9) 1 d PD A 2 N1P N 0.882(6) 0.7214(18) 0.0626(15) 0.046(10) Uiso 0.294(9) 1 d PD A 2 H1P1 H 0.9749 0.7491 0.0869 0.068 Uiso 0.294(9) 1 calc PR A 2 H1P2 H 0.7665 0.7497 0.0520 0.068 Uiso 0.294(9) 1 calc PR A 2 H1P3 H 0.9454 0.7055 0.0243 0.068 Uiso 0.294(9) 1 calc PR A 2 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 C1R 0.100(7) 0.096(7) 0.085(7) -0.017(5) -0.037(6) -0.012(6) C2R 0.103(7) 0.140(10) 0.130(9) 0.024(8) -0.006(7) 0.003(7) C3R 0.117(9) 0.147(13) 0.106(9) -0.014(8) 0.003(7) 0.006(9) C4R 0.156(10) 0.094(7) 0.119(9) -0.007(6) 0.008(7) -0.007(7) C5R 0.201(12) 0.126(10) 0.079(7) 0.025(6) 0.022(9) -0.012(10) C6R 0.132(8) 0.145(9) 0.085(6) -0.020(6) 0.002(6) 0.005(7) C7R 0.111(7) 0.097(6) 0.068(5) -0.022(4) 0.005(5) -0.010(6) C8R 0.100(7) 0.078(7) 0.115(7) 0.006(5) -0.009(6) -0.005(6) C9R 0.085(6) 0.068(5) 0.062(5) -0.010(4) -0.010(4) -0.010(5) C10R 0.061(5) 0.109(7) 0.083(6) -0.020(5) -0.013(4) -0.010(6) C11R 0.082(6) 0.087(8) 0.062(5) -0.012(4) -0.007(4) 0.008(6) C12R 0.057(6) 0.076(8) 0.064(6) -0.011(4) 0.000(4) -0.004(4) C13R 0.065(4) 0.075(6) 0.072(5) -0.031(4) 0.012(3) -0.016(4) C14R 0.094(6) 0.067(6) 0.077(5) -0.019(4) 0.024(4) -0.016(5) C15R 0.066(6) 0.069(6) 0.060(6) -0.008(4) -0.017(4) 0.014(5) C16R 0.088(7) 0.071(5) 0.070(5) 0.000(4) -0.006(4) -0.003(5) C17R 0.077(6) 0.071(6) 0.061(5) 0.009(3) 0.003(4) -0.001(5) C18R 0.091(6) 0.117(7) 0.072(5) 0.012(4) -0.011(5) -0.040(6) C19R 0.121(7) 0.124(7) 0.055(4) -0.001(5) 0.006(5) -0.034(5) C20R 0.159(8) 0.136(8) 0.073(5) 0.028(5) -0.002(6) -0.016(7) C21R 0.135(8) 0.157(12) 0.081(6) 0.028(7) 0.016(6) -0.032(8) C22R 0.105(8) 0.113(10) 0.084(7) 0.004(7) 0.012(6) -0.042(7) C23R 0.106(8) 0.082(7) 0.093(7) 0.010(6) -0.027(6) -0.015(7) O1R 0.192(8) 0.166(9) 0.106(5) -0.035(6) -0.013(6) -0.086(7) O2R 0.068(4) 0.118(9) 0.085(5) -0.015(5) -0.018(4) -0.024(5) O3R 0.077(5) 0.078(7) 0.049(4) -0.013(3) -0.010(2) -0.002(4) N1R 0.079(8) 0.113(11) 0.047(6) -0.012(4) 0.001(3) -0.009(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 C1R C2R 1.496(9) . ? C1R C7R 1.544(8) . ? C1R C6R 1.566(9) . ? C2R C3R 1.325(9) . ? C3R C4R 1.523(9) . ? C4R C5R 1.555(9) . ? C4R C7R 1.567(9) . ? C5R C6R 1.563(9) . ? C7R C8R 1.495(8) . ? C8R O1R 1.227(8) . ? C8R C9R 1.493(8) . ? C9R C14R 1.387(8) . ? C9R C10R 1.390(8) . ? C10R C11R 1.370(7) . ? C11R C12R 1.398(8) . ? C12R C13R 1.373(7) . ? C12R C15R 1.509(8) . ? C13R C14R 1.379(8) . ? C15R O2R 1.240(7) . ? C15R O3R 1.277(7) . ? C16R N1R 1.497(8) . ? C16R C23R 1.524(9) . ? C16R C17R 1.530(7) . ? C17R C18R 1.526(8) . ? C17R C22R 1.528(9) . ? C18R C19R 1.529(8) . ? C19R C20R 1.518(9) . ? C20R C21R 1.494(9) . ? C21R C22R 1.526(9) . ? C1P C7P 1.502(10) . ? C1P C6P 1.517(10) . ? C1P C2P 1.553(9) . ? C2P O1P 1.475(9) . ? C2P C3P 1.504(10) . ? C3P C4P 1.323(10) . ? C4P C5P 1.488(10) . ? C5P C6P 1.518(10) . ? C7P C8P 1.328(9) . ? C8P O1P 1.384(9) . ? C8P C9P 1.521(8) . ? C9P C14P 1.387(9) . ? C9P C10P 1.397(9) . ? C10P C11P 1.384(9) . ? C11P C12P 1.394(9) . ? C12P C13P 1.387(9) . ? C12P C15P 1.519(9) . ? C13P C14P 1.382(10) . ? C15P O2P 1.245(10) . ? C15P O3P 1.273(10) . ? C16P N1P 1.506(10) . ? C16P C23P 1.519(10) . ? C16P C17P 1.532(10) . ? C17P C22P 1.527(10) . ? C17P C18P 1.532(10) . ? C18P C19P 1.538(10) . ? C19P C20P 1.514(10) . ? C20P C21P 1.511(10) . ? C21P C22P 1.535(10) . ? 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 C2R C1R C7R 103.8(7) . . ? C2R C1R C6R 101.7(8) . . ? C7R C1R C6R 98.9(7) . . ? C3R C2R C1R 109.2(8) . . ? C2R C3R C4R 106.6(8) . . ? C3R C4R C5R 102.8(8) . . ? C3R C4R C7R 103.2(7) . . ? C5R C4R C7R 99.2(6) . . ? C4R C5R C6R 102.4(6) . . ? C5R C6R C1R 103.2(6) . . ? C8R C7R C1R 112.2(7) . . ? C8R C7R C4R 113.5(7) . . ? C1R C7R C4R 92.9(6) . . ? O1R C8R C9R 118.6(7) . . ? O1R C8R C7R 122.1(7) . . ? C9R C8R C7R 119.3(7) . . ? C14R C9R C10R 117.4(6) . . ? C14R C9R C8R 125.1(7) . . ? C10R C9R C8R 117.6(7) . . ? C11R C10R C9R 121.5(7) . . ? C10R C11R C12R 120.0(8) . . ? C13R C12R C11R 119.1(7) . . ? C13R C12R C15R 120.5(7) . . ? C11R C12R C15R 120.0(6) . . ? C12R C13R C14R 120.0(7) . . ? C13R C14R C9R 121.8(6) . . ? O2R C15R O3R 123.9(8) . . ? O2R C15R C12R 119.2(7) . . ? O3R C15R C12R 116.6(6) . . ? N1R C16R C23R 108.9(8) . . ? N1R C16R C17R 110.1(8) . . ? C23R C16R C17R 113.1(8) . . ? C18R C17R C22R 110.6(7) . . ? C18R C17R C16R 112.2(7) . . ? C22R C17R C16R 110.7(7) . . ? C17R C18R C19R 113.0(7) . . ? C20R C19R C18R 111.4(8) . . ? C21R C20R C19R 112.2(8) . . ? C20R C21R C22R 113.4(8) . . ? C21R C22R C17R 110.6(8) . . ? C7P C1P C6P 112.5(14) . . ? C7P C1P C2P 100.6(9) . . ? C6P C1P C2P 114.6(12) . . ? O1P C2P C3P 109.7(14) . . ? O1P C2P C1P 104.4(8) . . ? C3P C2P C1P 111.9(10) . . ? C4P C3P C2P 122.2(13) . . ? C3P C4P C5P 126.1(13) . . ? C4P C5P C6P 111.8(12) . . ? C1P C6P C5P 113.9(12) . . ? C8P C7P C1P 105.2(10) . . ? C7P C8P O1P 117.3(9) . . ? C7P C8P C9P 124.9(10) . . ? O1P C8P C9P 117.1(9) . . ? C14P C9P C10P 119.8(10) . . ? C14P C9P C8P 120.4(11) . . ? C10P C9P C8P 119.8(11) . . ? C11P C10P C9P 119.9(12) . . ? C10P C11P C12P 120.0(11) . . ? C13P C12P C11P 119.6(11) . . ? C13P C12P C15P 119.0(12) . . ? C11P C12P C15P 121.1(11) . . ? C14P C13P C12P 120.2(12) . . ? C13P C14P C9P 120.0(12) . . ? O2P C15P O3P 123.1(16) . . ? O2P C15P C12P 116.8(13) . . ? O3P C15P C12P 116.9(15) . . ? N1P C16P C23P 107.9(14) . . ? N1P C16P C17P 109.5(14) . . ? C23P C16P C17P 116.7(14) . . ? C22P C17P C18P 110.7(14) . . ? C22P C17P C16P 112.5(13) . . ? C18P C17P C16P 111.3(14) . . ? C17P C18P C19P 112.2(13) . . ? C20P C19P C18P 111.2(14) . . ? C21P C20P C19P 112.5(14) . . ? C20P C21P C22P 112.6(14) . . ? C17P C22P C21P 110.4(13) . . ? C8P O1P C2P 103.3(8) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.269 _refine_diff_density_min -0.264 _refine_diff_density_rms 0.076 #===END data_30.0%P _database_code_depnum_ccdc_archive 'CCDC 608925' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1732(10) _cell_length_b 17.519(3) _cell_length_c 19.547(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2114.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 14 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.161 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9595 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11413 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.0585 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3691 _reflns_number_gt 1865 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.030(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3691 _refine_ls_number_parameters 354 _refine_ls_number_restraints 225 _refine_ls_R_factor_all 0.1688 _refine_ls_R_factor_gt 0.1208 _refine_ls_wR_factor_ref 0.3508 _refine_ls_wR_factor_gt 0.3245 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.124 _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 C1R C 0.830(2) 0.9757(6) 0.4843(5) 0.105(4) Uani 0.700(11) 1 d PDU A 1 H1R H 0.8288 1.0316 0.4843 0.126 Uiso 0.700(11) 1 calc PR A 1 C2R C 1.0498(19) 0.9384(10) 0.4824(9) 0.146(5) Uani 0.700(11) 1 d PDU A 1 H2R H 1.1804 0.9610 0.4946 0.175 Uiso 0.700(11) 1 calc PR A 1 C3R C 1.024(2) 0.8674(10) 0.4602(9) 0.140(8) Uani 0.700(11) 1 d PD A 1 H3R H 1.1334 0.8317 0.4532 0.168 Uiso 0.700(11) 1 calc PR A 1 C4R C 0.783(2) 0.8550(6) 0.4481(6) 0.151(6) Uani 0.700(11) 1 d PD A 1 H4R H 0.7437 0.8127 0.4177 0.182 Uiso 0.700(11) 1 calc PR A 1 C5R C 0.688(3) 0.8524(8) 0.5218(7) 0.151(6) Uani 0.700(11) 1 d PD A 1 H5R1 H 0.7653 0.8158 0.5500 0.181 Uiso 0.700(11) 1 calc PR A 1 H5R2 H 0.5356 0.8396 0.5213 0.181 Uiso 0.700(11) 1 calc PR A 1 C6R C 0.726(3) 0.9357(9) 0.5476(6) 0.130(12) Uani 0.700(11) 1 d PD A 1 H6R1 H 0.8225 0.9367 0.5866 0.156 Uiso 0.700(11) 1 calc PR A 1 H6R2 H 0.5899 0.9598 0.5600 0.156 Uiso 0.700(11) 1 calc PR A 1 C7R C 0.703(2) 0.9362(7) 0.4264(4) 0.112(5) Uani 0.700(11) 1 d PD A 1 H7R H 0.5457 0.9423 0.4312 0.134 Uiso 0.700(11) 1 calc PR A 1 C8R C 0.7837(18) 0.9585(7) 0.3568(4) 0.114(4) Uani 0.700(11) 1 d PDU A 1 C9R C 0.6838(16) 0.9243(6) 0.2946(4) 0.075(3) Uani 0.700(11) 1 d PD A 1 C10R C 0.8104(18) 0.9200(9) 0.2357(5) 0.092(4) Uani 0.700(11) 1 d PDU A 1 H10R H 0.9536 0.9364 0.2370 0.111 Uiso 0.700(11) 1 calc PR A 1 C11R C 0.7257(19) 0.8918(10) 0.1758(5) 0.085(4) Uani 0.700(11) 1 d PDU A 1 H11R H 0.8129 0.8882 0.1371 0.102 Uiso 0.700(11) 1 calc PR A 1 C12R C 0.5093(19) 0.8684(11) 0.1725(5) 0.073(4) Uani 0.700(11) 1 d PDU A 1 C13R C 0.3893(15) 0.8664(7) 0.2319(4) 0.075(3) Uani 0.700(11) 1 d PDU A 1 H13R H 0.2496 0.8465 0.2314 0.091 Uiso 0.700(11) 1 calc PR A 1 C14R C 0.4760(15) 0.8937(8) 0.2923(4) 0.082(3) Uani 0.700(11) 1 d PD A 1 H14R H 0.3939 0.8917 0.3322 0.098 Uiso 0.700(11) 1 calc PR A 1 C15R C 0.4258(17) 0.8308(9) 0.1081(5) 0.080(5) Uani 0.700(11) 1 d PD A 1 C16R C 0.778(2) 0.6551(10) 0.0984(5) 0.085(4) Uani 0.700(11) 1 d PDU A 1 H16R H 0.8819 0.6133 0.0933 0.102 Uiso 0.700(11) 1 calc PR A 1 C17R C 0.738(2) 0.6678(7) 0.1750(4) 0.078(4) Uani 0.700(11) 1 d PD A 1 H17R H 0.6375 0.7107 0.1795 0.093 Uiso 0.700(11) 1 calc PR A 1 C18R C 0.946(2) 0.6897(12) 0.2126(5) 0.106(4) Uani 0.700(11) 1 d PDU A 1 H18A H 1.0008 0.7369 0.1936 0.127 Uiso 0.700(11) 1 calc PR A 1 H18B H 1.0536 0.6504 0.2050 0.127 Uiso 0.700(11) 1 calc PR A 1 C19R C 0.912(3) 0.6998(9) 0.2897(5) 0.117(4) Uani 0.700(11) 1 d PDU A 1 H19A H 1.0516 0.7071 0.3115 0.141 Uiso 0.700(11) 1 calc PR A 1 H19B H 0.8260 0.7452 0.2977 0.141 Uiso 0.700(11) 1 calc PR A 1 C20R C 0.800(3) 0.6319(9) 0.3221(6) 0.147(6) Uani 0.700(11) 1 d PDU A 1 H20A H 0.8967 0.5883 0.3216 0.177 Uiso 0.700(11) 1 calc PR A 1 H20B H 0.7656 0.6436 0.3694 0.177 Uiso 0.700(11) 1 calc PR A 1 C21R C 0.595(2) 0.6121(10) 0.2844(5) 0.119(4) Uani 0.700(11) 1 d PDU A 1 H21A H 0.4914 0.6533 0.2901 0.143 Uiso 0.700(11) 1 calc PR A 1 H21B H 0.5323 0.5665 0.3045 0.143 Uiso 0.700(11) 1 calc PR A 1 C22R C 0.632(2) 0.5985(9) 0.2083(5) 0.106(5) Uani 0.700(11) 1 d PD A 1 H22A H 0.4942 0.5883 0.1862 0.127 Uiso 0.700(11) 1 calc PR A 1 H22B H 0.7237 0.5541 0.2022 0.127 Uiso 0.700(11) 1 calc PR A 1 C23R C 0.574(3) 0.6344(11) 0.0583(8) 0.108(6) Uani 0.700(11) 1 d PD A 1 H23A H 0.6121 0.6224 0.0119 0.163 Uiso 0.700(11) 1 calc PR A 1 H23B H 0.4754 0.6768 0.0587 0.163 Uiso 0.700(11) 1 calc PR A 1 H23C H 0.5056 0.5909 0.0791 0.163 Uiso 0.700(11) 1 calc PR A 1 O1R O 0.942(2) 1.0008(9) 0.3493(6) 0.182(6) Uani 0.700(11) 1 d PD A 1 O2R O 0.2333(16) 0.8101(10) 0.1060(6) 0.099(4) Uani 0.700(11) 1 d PD A 1 O3R O 0.5480(14) 0.8342(7) 0.0557(4) 0.071(2) Uani 0.700(11) 1 d PDU A 1 N1R N 0.875(4) 0.7260(13) 0.0674(8) 0.083(8) Uani 0.700(11) 1 d PD A 1 H1R1 H 0.8996 0.7183 0.0231 0.124 Uiso 0.700(11) 1 calc PR A 1 H1R2 H 0.9995 0.7367 0.0884 0.124 Uiso 0.700(11) 1 calc PR A 1 H1R3 H 0.7839 0.7649 0.0726 0.124 Uiso 0.700(11) 1 calc PR A 1 C1P C 0.792(4) 0.9718(14) 0.4747(9) 0.110(8) Uiso 0.300(11) 1 d PDU A 2 H1P H 0.7825 1.0275 0.4729 0.131 Uiso 0.300(11) 1 calc PR A 2 C2P C 1.011(3) 0.9439(13) 0.4442(8) 0.111(8) Uiso 0.300(11) 1 d PDU A 2 H2P H 1.1264 0.9809 0.4538 0.133 Uiso 0.300(11) 1 calc PR A 2 C3P C 1.073(4) 0.8663(17) 0.4707(16) 0.106(13) Uiso 0.300(11) 1 d PD A 2 H3P H 1.2043 0.8457 0.4568 0.127 Uiso 0.300(11) 1 calc PR A 2 C4P C 0.951(4) 0.8257(12) 0.5128(12) 0.098(8) Uiso 0.300(11) 1 d PD A 2 H4P H 0.9811 0.7739 0.5169 0.118 Uiso 0.300(11) 1 calc PR A 2 C5P C 0.768(5) 0.8567(16) 0.5541(16) 0.130(13) Uiso 0.300(11) 1 d PD A 2 H5P1 H 0.7883 0.8434 0.6019 0.155 Uiso 0.300(11) 1 calc PR A 2 H5P2 H 0.6327 0.8339 0.5389 0.155 Uiso 0.300(11) 1 calc PR A 2 C6P C 0.754(7) 0.9431(17) 0.5471(10) 0.13(3) Uiso 0.300(11) 1 d PD A 2 H6P1 H 0.8596 0.9662 0.5774 0.156 Uiso 0.300(11) 1 calc PR A 2 H6P2 H 0.6113 0.9597 0.5620 0.156 Uiso 0.300(11) 1 calc PR A 2 C7P C 0.639(3) 0.936(3) 0.4243(11) 0.150(19) Uiso 0.300(11) 1 d PD A 2 H7P H 0.4965 0.9206 0.4325 0.180 Uiso 0.300(11) 1 calc PR A 2 C8P C 0.747(3) 0.9302(16) 0.3658(9) 0.091(7) Uiso 0.300(11) 1 d PDU A 2 C9P C 0.654(3) 0.9059(12) 0.2972(9) 0.073(10) Uiso 0.300(11) 1 d PD A 2 C10P C 0.762(4) 0.9275(19) 0.2373(10) 0.083(8) Uiso 0.300(11) 1 d PDU A 2 H10P H 0.8873 0.9571 0.2399 0.099 Uiso 0.300(11) 1 calc PR A 2 C11P C 0.684(4) 0.9047(19) 0.1742(10) 0.056(7) Uiso 0.300(11) 1 d PDU A 2 H11P H 0.7600 0.9168 0.1346 0.067 Uiso 0.300(11) 1 calc PR A 2 C12P C 0.490(5) 0.864(2) 0.1696(9) 0.070(8) Uiso 0.300(11) 1 d PDU A 2 C13P C 0.391(4) 0.8388(17) 0.2292(9) 0.094(9) Uiso 0.300(11) 1 d PDU A 2 H13P H 0.2750 0.8049 0.2268 0.113 Uiso 0.300(11) 1 calc PR A 2 C14P C 0.464(4) 0.8640(18) 0.2924(10) 0.107(15) Uiso 0.300(11) 1 d PD A 2 H14P H 0.3847 0.8529 0.3317 0.128 Uiso 0.300(11) 1 calc PR A 2 C15P C 0.392(3) 0.8429(16) 0.1009(9) 0.058(11) Uiso 0.300(11) 1 d PD A 2 C16P C 0.807(5) 0.652(2) 0.1058(11) 0.076(7) Uiso 0.300(11) 1 d PDU A 2 H16P H 0.9199 0.6126 0.1060 0.091 Uiso 0.300(11) 1 calc PR A 2 C17P C 0.776(5) 0.678(2) 0.1800(12) 0.097(14) Uiso 0.300(11) 1 d PD A 2 H17P H 0.7030 0.7282 0.1786 0.116 Uiso 0.300(11) 1 calc PR A 2 C18P C 0.992(5) 0.689(3) 0.2169(16) 0.119(9) Uiso 0.300(11) 1 d PDU A 2 H18C H 1.0799 0.7257 0.1916 0.143 Uiso 0.300(11) 1 calc PR A 2 H18D H 1.0694 0.6412 0.2178 0.143 Uiso 0.300(11) 1 calc PR A 2 C19P C 0.962(6) 0.718(2) 0.2905(16) 0.122(9) Uiso 0.300(11) 1 d PDU A 2 H19C H 1.1019 0.7217 0.3128 0.146 Uiso 0.300(11) 1 calc PR A 2 H19D H 0.8991 0.7690 0.2895 0.146 Uiso 0.300(11) 1 calc PR A 2 C20P C 0.816(6) 0.666(3) 0.3313(14) 0.166(11) Uiso 0.300(11) 1 d PDU A 2 H20C H 0.8896 0.6174 0.3388 0.199 Uiso 0.300(11) 1 calc PR A 2 H20D H 0.7865 0.6882 0.3756 0.199 Uiso 0.300(11) 1 calc PR A 2 C21P C 0.604(5) 0.651(2) 0.2948(13) 0.120(9) Uiso 0.300(11) 1 d PDU A 2 H21C H 0.5194 0.6975 0.2951 0.144 Uiso 0.300(11) 1 calc PR A 2 H21D H 0.5240 0.6125 0.3199 0.144 Uiso 0.300(11) 1 calc PR A 2 C22P C 0.631(5) 0.6241(19) 0.2206(13) 0.100(13) Uiso 0.300(11) 1 d PD A 2 H22C H 0.6935 0.5734 0.2201 0.120 Uiso 0.300(11) 1 calc PR A 2 H22D H 0.4894 0.6213 0.1990 0.120 Uiso 0.300(11) 1 calc PR A 2 C23P C 0.609(5) 0.619(2) 0.0704(16) 0.074(10) Uiso 0.300(11) 1 d PD A 2 H23D H 0.6453 0.6056 0.0241 0.111 Uiso 0.300(11) 1 calc PR A 2 H23E H 0.4945 0.6558 0.0703 0.111 Uiso 0.300(11) 1 calc PR A 2 H23F H 0.5624 0.5739 0.0943 0.111 Uiso 0.300(11) 1 calc PR A 2 O1P O 0.969(2) 0.9400(11) 0.3701(7) 0.084(5) Uiso 0.300(11) 1 d PD A 2 O2P O 0.192(3) 0.832(2) 0.0999(16) 0.101(13) Uiso 0.300(11) 1 d PD A 2 O3P O 0.517(4) 0.812(2) 0.0569(15) 0.106(12) Uiso 0.300(11) 1 d PDU A 2 N1P N 0.889(8) 0.717(3) 0.0625(17) 0.059(12) Uiso 0.300(11) 1 d PD A 2 H1P1 H 0.9820 0.7452 0.0865 0.089 Uiso 0.300(11) 1 calc PR A 2 H1P2 H 0.7773 0.7464 0.0498 0.089 Uiso 0.300(11) 1 calc PR A 2 H1P3 H 0.9543 0.6989 0.0254 0.089 Uiso 0.300(11) 1 calc PR A 2 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 C1R 0.125(9) 0.114(8) 0.076(7) -0.016(6) -0.025(6) 0.010(7) C2R 0.135(10) 0.143(11) 0.160(13) 0.027(10) 0.010(10) 0.005(10) C3R 0.139(14) 0.157(16) 0.124(13) -0.007(10) -0.014(11) 0.008(12) C4R 0.183(16) 0.104(11) 0.167(15) -0.015(9) 0.017(12) 0.005(10) C5R 0.215(16) 0.138(13) 0.099(10) 0.025(9) 0.021(12) -0.029(13) C6R 0.119(12) 0.16(2) 0.107(12) -0.025(9) 0.004(8) 0.011(9) C7R 0.168(12) 0.110(10) 0.058(6) -0.019(6) 0.013(7) 0.002(10) C8R 0.108(8) 0.091(9) 0.142(10) 0.006(7) -0.019(7) 0.008(7) C9R 0.092(7) 0.067(6) 0.065(6) -0.011(4) -0.009(5) -0.012(6) C10R 0.066(6) 0.118(9) 0.093(7) -0.020(6) -0.019(5) -0.013(7) C11R 0.087(8) 0.100(9) 0.067(6) -0.017(5) -0.003(5) 0.009(7) C12R 0.061(5) 0.089(7) 0.067(6) -0.019(4) -0.005(4) -0.006(5) C13R 0.076(5) 0.069(7) 0.081(6) -0.031(5) 0.015(4) -0.008(5) C14R 0.102(9) 0.067(7) 0.077(7) -0.013(5) 0.028(5) 0.001(6) C15R 0.079(7) 0.082(8) 0.078(8) -0.004(6) -0.028(6) 0.024(6) C16R 0.096(8) 0.078(6) 0.082(7) 0.000(5) -0.008(6) -0.001(6) C17R 0.090(7) 0.075(7) 0.067(6) 0.005(5) -0.006(5) -0.003(6) C18R 0.099(8) 0.135(9) 0.085(6) 0.017(6) -0.018(6) -0.032(8) C19R 0.138(10) 0.156(11) 0.058(5) -0.001(6) 0.013(6) -0.048(8) C20R 0.206(12) 0.164(13) 0.073(7) 0.026(8) -0.015(9) -0.033(11) C21R 0.137(9) 0.147(12) 0.073(7) 0.031(7) 0.019(7) -0.021(8) C22R 0.128(11) 0.098(10) 0.091(8) -0.015(7) 0.016(7) -0.037(8) C23R 0.124(11) 0.101(11) 0.100(10) 0.013(8) -0.039(8) -0.024(9) O1R 0.223(12) 0.192(14) 0.129(8) -0.050(9) -0.002(8) -0.085(11) O2R 0.068(5) 0.129(11) 0.100(6) -0.025(6) -0.020(4) -0.021(6) O3R 0.078(4) 0.089(6) 0.047(4) -0.016(3) -0.008(3) -0.010(4) N1R 0.079(9) 0.115(13) 0.054(6) -0.016(5) 0.008(4) 0.004(7) _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 C1R C2R 1.504(9) . ? C1R C7R 1.542(9) . ? C1R C6R 1.562(9) . ? C2R C3R 1.327(9) . ? C3R C4R 1.521(9) . ? C4R C5R 1.556(9) . ? C4R C7R 1.564(9) . ? C5R C6R 1.561(9) . ? C7R C8R 1.501(8) . ? C8R O1R 1.236(8) . ? C8R C9R 1.489(8) . ? C9R C14R 1.391(8) . ? C9R C10R 1.393(8) . ? C10R C11R 1.375(8) . ? C11R C12R 1.399(8) . ? C12R C13R 1.378(8) . ? C12R C15R 1.511(8) . ? C13R C14R 1.382(8) . ? C15R O2R 1.243(8) . ? C15R O3R 1.274(8) . ? C16R N1R 1.508(8) . ? C16R C23R 1.526(9) . ? C16R C17R 1.534(8) . ? C17R C18R 1.523(9) . ? C17R C22R 1.527(9) . ? C18R C19R 1.532(9) . ? C19R C20R 1.515(9) . ? C20R C21R 1.505(9) . ? C21R C22R 1.524(9) . ? C1P C7P 1.507(10) . ? C1P C6P 1.521(10) . ? C1P C2P 1.555(10) . ? C2P O1P 1.472(9) . ? C2P C3P 1.504(10) . ? C3P C4P 1.323(10) . ? C4P C5P 1.492(10) . ? C5P C6P 1.521(10) . ? C7P C8P 1.330(9) . ? C8P O1P 1.385(9) . ? C8P C9P 1.521(8) . ? C9P C14P 1.389(9) . ? C9P C10P 1.401(9) . ? C10P C11P 1.385(9) . ? C11P C12P 1.394(9) . ? C12P C13P 1.389(9) . ? C12P C15P 1.520(9) . ? C13P C14P 1.386(9) . ? C15P O2P 1.250(10) . ? C15P O3P 1.277(10) . ? C16P N1P 1.508(10) . ? C16P C23P 1.523(10) . ? C16P C17P 1.534(10) . ? C17P C22P 1.529(10) . ? C17P C18P 1.532(10) . ? C18P C19P 1.538(10) . ? C19P C20P 1.517(10) . ? C20P C21P 1.509(10) . ? C21P C22P 1.532(10) . ? 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 C2R C1R C7R 104.3(8) . . ? C2R C1R C6R 101.4(9) . . ? C7R C1R C6R 99.7(7) . . ? C3R C2R C1R 107.9(9) . . ? C2R C3R C4R 107.5(9) . . ? C3R C4R C5R 103.1(10) . . ? C3R C4R C7R 102.9(8) . . ? C5R C4R C7R 99.1(7) . . ? C4R C5R C6R 102.5(7) . . ? C5R C6R C1R 103.0(7) . . ? C8R C7R C1R 112.2(8) . . ? C8R C7R C4R 112.1(8) . . ? C1R C7R C4R 92.7(6) . . ? O1R C8R C9R 118.2(8) . . ? O1R C8R C7R 121.8(9) . . ? C9R C8R C7R 119.8(8) . . ? C14R C9R C10R 118.1(7) . . ? C14R C9R C8R 124.3(7) . . ? C10R C9R C8R 117.6(8) . . ? C11R C10R C9R 120.7(8) . . ? C10R C11R C12R 120.5(8) . . ? C13R C12R C11R 118.8(7) . . ? C13R C12R C15R 120.5(7) . . ? C11R C12R C15R 119.5(7) . . ? C12R C13R C14R 120.2(7) . . ? C13R C14R C9R 121.2(7) . . ? O2R C15R O3R 123.6(8) . . ? O2R C15R C12R 118.7(7) . . ? O3R C15R C12R 116.5(7) . . ? N1R C16R C23R 108.6(9) . . ? N1R C16R C17R 109.5(8) . . ? C23R C16R C17R 114.0(9) . . ? C18R C17R C22R 110.9(8) . . ? C18R C17R C16R 112.0(7) . . ? C22R C17R C16R 111.6(8) . . ? C17R C18R C19R 112.9(8) . . ? C20R C19R C18R 112.5(9) . . ? C21R C20R C19R 111.1(9) . . ? C20R C21R C22R 112.8(9) . . ? C21R C22R C17R 110.9(9) . . ? C7P C1P C6P 111.8(14) . . ? C7P C1P C2P 99.5(10) . . ? C6P C1P C2P 113.0(13) . . ? O1P C2P C3P 109.9(14) . . ? O1P C2P C1P 103.9(9) . . ? C3P C2P C1P 111.7(11) . . ? C4P C3P C2P 123.8(13) . . ? C3P C4P C5P 124.9(13) . . ? C4P C5P C6P 110.9(12) . . ? C5P C6P C1P 113.8(13) . . ? C8P C7P C1P 106.0(11) . . ? C7P C8P O1P 116.0(9) . . ? C7P C8P C9P 126.0(11) . . ? O1P C8P C9P 117.6(10) . . ? C14P C9P C10P 119.4(10) . . ? C14P C9P C8P 121.9(11) . . ? C10P C9P C8P 118.7(11) . . ? C11P C10P C9P 119.9(12) . . ? C10P C11P C12P 120.4(12) . . ? C13P C12P C11P 119.2(11) . . ? C13P C12P C15P 119.2(12) . . ? C11P C12P C15P 121.6(12) . . ? C14P C13P C12P 120.2(12) . . ? C13P C14P C9P 120.2(12) . . ? O2P C15P O3P 121.8(16) . . ? O2P C15P C12P 116.4(14) . . ? O3P C15P C12P 117.0(15) . . ? N1P C16P C23P 107.6(14) . . ? N1P C16P C17P 110.2(14) . . ? C23P C16P C17P 116.2(14) . . ? C22P C17P C18P 110.1(14) . . ? C22P C17P C16P 112.2(13) . . ? C18P C17P C16P 111.7(14) . . ? C17P C18P C19P 112.0(14) . . ? C20P C19P C18P 111.3(14) . . ? C21P C20P C19P 111.7(14) . . ? C20P C21P C22P 114.1(14) . . ? C17P C22P C21P 111.3(13) . . ? C8P O1P C2P 103.8(9) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.357 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.097 #===END data_30.7%P _database_code_depnum_ccdc_archive 'CCDC 608926' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1783(12) _cell_length_b 17.515(3) _cell_length_c 19.569(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2117.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 14 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9595 _exptl_absorpt_correction_T_max 0.9776 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11451 _diffrn_reflns_av_R_equivalents 0.0705 _diffrn_reflns_av_sigmaI/netI 0.0671 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3706 _reflns_number_gt 1732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3706 _refine_ls_number_parameters 353 _refine_ls_number_restraints 261 _refine_ls_R_factor_all 0.2027 _refine_ls_R_factor_gt 0.1412 _refine_ls_wR_factor_ref 0.3968 _refine_ls_wR_factor_gt 0.3667 _refine_ls_goodness_of_fit_ref 1.223 _refine_ls_restrained_S_all 1.225 _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 C1R C 0.827(3) 0.9753(7) 0.4844(5) 0.119(5) Uani 0.693(12) 1 d PDU A 1 H1R H 0.8246 1.0312 0.4842 0.143 Uiso 0.693(12) 1 calc PR A 1 C2R C 1.047(2) 0.9382(11) 0.4816(10) 0.158(7) Uani 0.693(12) 1 d PDU A 1 H2R H 1.1779 0.9612 0.4931 0.190 Uiso 0.693(12) 1 calc PR A 1 C3R C 1.023(2) 0.8672(11) 0.4600(10) 0.145(9) Uani 0.693(12) 1 d PD A 1 H3R H 1.1329 0.8318 0.4532 0.174 Uiso 0.693(12) 1 calc PR A 1 C4R C 0.782(3) 0.8537(7) 0.4480(7) 0.171(8) Uani 0.693(12) 1 d PD A 1 H4R H 0.7427 0.8113 0.4178 0.205 Uiso 0.693(12) 1 calc PR A 1 C5R C 0.687(3) 0.8520(8) 0.5221(8) 0.143(6) Uani 0.693(12) 1 d PDU A 1 H5R1 H 0.5342 0.8395 0.5217 0.171 Uiso 0.693(12) 1 calc PR A 1 H5R2 H 0.7632 0.8153 0.5504 0.171 Uiso 0.693(12) 1 calc PR A 1 C6R C 0.726(3) 0.9353(9) 0.5478(6) 0.131(5) Uani 0.693(12) 1 d PDU A 1 H6R1 H 0.5907 0.9594 0.5608 0.157 Uiso 0.693(12) 1 calc PR A 1 H6R2 H 0.8242 0.9361 0.5864 0.157 Uiso 0.693(12) 1 calc PR A 1 C7R C 0.704(2) 0.9351(8) 0.4264(5) 0.118(5) Uani 0.693(12) 1 d PDU A 1 H7R H 0.5468 0.9409 0.4310 0.142 Uiso 0.693(12) 1 calc PR A 1 C8R C 0.783(2) 0.9587(8) 0.3571(5) 0.120(5) Uani 0.693(12) 1 d PDU A 1 C9R C 0.6842(19) 0.9243(7) 0.2950(5) 0.085(5) Uani 0.693(12) 1 d PD A 1 C10R C 0.810(2) 0.9197(11) 0.2358(6) 0.095(4) Uani 0.693(12) 1 d PDU A 1 H10R H 0.9531 0.9366 0.2366 0.115 Uiso 0.693(12) 1 calc PR A 1 C11R C 0.725(2) 0.8901(13) 0.1763(6) 0.098(6) Uani 0.693(12) 1 d PDU A 1 H11R H 0.8122 0.8853 0.1378 0.117 Uiso 0.693(12) 1 calc PR A 1 C12R C 0.508(2) 0.8673(14) 0.1734(6) 0.086(11) Uani 0.693(12) 1 d PD A 1 C13R C 0.3884(19) 0.8648(7) 0.2331(5) 0.082(3) Uani 0.693(12) 1 d PDU A 1 H13R H 0.2484 0.8453 0.2329 0.099 Uiso 0.693(12) 1 calc PR A 1 C14R C 0.4786(18) 0.8914(10) 0.2932(5) 0.088(4) Uani 0.693(12) 1 d PD A 1 H14R H 0.4000 0.8872 0.3335 0.106 Uiso 0.693(12) 1 calc PR A 1 C15R C 0.4218(17) 0.8309(8) 0.1088(5) 0.073(3) Uani 0.693(12) 1 d PDU A 1 C16R C 0.794(3) 0.6550(10) 0.0992(6) 0.086(4) Uani 0.693(12) 1 d PDU A 1 H16R H 0.9099 0.6170 0.0971 0.104 Uiso 0.693(12) 1 calc PR A 1 C17R C 0.739(3) 0.6689(9) 0.1750(5) 0.096(10) Uani 0.693(12) 1 d PD A 1 H17R H 0.6322 0.7101 0.1778 0.115 Uiso 0.693(12) 1 calc PR A 1 C18R C 0.943(2) 0.6940(9) 0.2135(5) 0.099(4) Uani 0.693(12) 1 d PDU A 1 H18A H 0.9975 0.7408 0.1934 0.118 Uiso 0.693(12) 1 calc PR A 1 H18B H 1.0539 0.6551 0.2083 0.118 Uiso 0.693(12) 1 calc PR A 1 C19R C 0.902(3) 0.7072(9) 0.2900(6) 0.110(5) Uani 0.693(12) 1 d PDU A 1 H19A H 1.0381 0.7178 0.3128 0.132 Uiso 0.693(12) 1 calc PR A 1 H19B H 0.8088 0.7513 0.2958 0.132 Uiso 0.693(12) 1 calc PR A 1 C20R C 0.796(4) 0.6380(13) 0.3229(8) 0.180(7) Uani 0.693(12) 1 d PDU A 1 H20A H 0.9020 0.5973 0.3261 0.216 Uiso 0.693(12) 1 calc PR A 1 H20B H 0.7517 0.6512 0.3689 0.216 Uiso 0.693(12) 1 calc PR A 1 C21R C 0.601(3) 0.6092(11) 0.2837(6) 0.124(5) Uani 0.693(12) 1 d PDU A 1 H21A H 0.4839 0.6455 0.2890 0.149 Uiso 0.693(12) 1 calc PR A 1 H21B H 0.5546 0.5612 0.3036 0.149 Uiso 0.693(12) 1 calc PR A 1 C22R C 0.642(3) 0.5970(9) 0.2079(7) 0.111(5) Uani 0.693(12) 1 d PDU A 1 H22A H 0.5063 0.5845 0.1854 0.134 Uiso 0.693(12) 1 calc PR A 1 H22B H 0.7400 0.5544 0.2017 0.134 Uiso 0.693(12) 1 calc PR A 1 C23R C 0.605(4) 0.6257(17) 0.0564(11) 0.123(8) Uani 0.693(12) 1 d PD A 1 H23A H 0.6541 0.6148 0.0110 0.185 Uiso 0.693(12) 1 calc PR A 1 H23B H 0.4935 0.6640 0.0547 0.185 Uiso 0.693(12) 1 calc PR A 1 H23C H 0.5478 0.5801 0.0768 0.185 Uiso 0.693(12) 1 calc PR A 1 O1R O 0.945(3) 0.9990(11) 0.3497(7) 0.193(7) Uani 0.693(12) 1 d PDU A 1 O2R O 0.2318(16) 0.8082(9) 0.1063(6) 0.099(4) Uani 0.693(12) 1 d PDU A 1 O3R O 0.5457(19) 0.8346(10) 0.0568(5) 0.079(4) Uani 0.693(12) 1 d PDU A 1 N1R N 0.876(3) 0.7277(11) 0.0671(7) 0.080(6) Uani 0.693(12) 1 d PD A 1 H1R1 H 0.9005 0.7199 0.0228 0.119 Uiso 0.693(12) 1 calc PR A 1 H1R2 H 0.9988 0.7416 0.0874 0.119 Uiso 0.693(12) 1 calc PR A 1 H1R3 H 0.7778 0.7644 0.0721 0.119 Uiso 0.693(12) 1 calc PR A 1 C1P C 0.795(5) 0.9739(15) 0.4746(10) 0.118(9) Uiso 0.307(12) 1 d PDU A 2 H1P H 0.7892 1.0298 0.4734 0.142 Uiso 0.307(12) 1 calc PR A 2 C2P C 1.012(3) 0.9449(14) 0.4444(9) 0.133(10) Uiso 0.307(12) 1 d PDU A 2 H2P H 1.1262 0.9829 0.4518 0.160 Uiso 0.307(12) 1 calc PR A 2 C3P C 1.079(5) 0.8693(19) 0.4740(16) 0.110(15) Uiso 0.307(12) 1 d PD A 2 H3P H 1.2176 0.8515 0.4643 0.132 Uiso 0.307(12) 1 calc PR A 2 C4P C 0.952(5) 0.8266(14) 0.5131(16) 0.125(12) Uiso 0.307(12) 1 d PD A 2 H4P H 0.9785 0.7743 0.5151 0.150 Uiso 0.307(12) 1 calc PR A 2 C5P C 0.769(5) 0.8586(18) 0.5541(18) 0.131(10) Uiso 0.307(12) 1 d PDU A 2 H5P1 H 0.7891 0.8456 0.6018 0.158 Uiso 0.307(12) 1 calc PR A 2 H5P2 H 0.6342 0.8359 0.5389 0.158 Uiso 0.307(12) 1 calc PR A 2 C6P C 0.755(7) 0.9450(18) 0.5468(10) 0.126(9) Uiso 0.307(12) 1 d PDU A 2 H6P1 H 0.6124 0.9615 0.5614 0.151 Uiso 0.307(12) 1 calc PR A 2 H6P2 H 0.8601 0.9682 0.5772 0.151 Uiso 0.307(12) 1 calc PR A 2 C7P C 0.638(3) 0.941(3) 0.4239(12) 0.119(9) Uiso 0.307(12) 1 d PDU A 2 H7P H 0.4915 0.9312 0.4312 0.143 Uiso 0.307(12) 1 calc PR A 2 C8P C 0.748(3) 0.9273(17) 0.3670(9) 0.091(8) Uiso 0.307(12) 1 d PDU A 2 C9P C 0.656(3) 0.9039(13) 0.2980(9) 0.071(10) Uiso 0.307(12) 1 d PD A 2 C10P C 0.769(5) 0.925(2) 0.2387(11) 0.088(8) Uiso 0.307(12) 1 d PDU A 2 H10P H 0.8960 0.9528 0.2421 0.106 Uiso 0.307(12) 1 calc PR A 2 C11P C 0.692(5) 0.903(2) 0.1750(10) 0.063(7) Uiso 0.307(12) 1 d PDU A 2 H11P H 0.7706 0.9148 0.1359 0.075 Uiso 0.307(12) 1 calc PR A 2 C12P C 0.496(5) 0.864(2) 0.1700(9) 0.064(18) Uiso 0.307(12) 1 d PD A 2 C13P C 0.393(4) 0.8387(18) 0.2290(10) 0.088(5) Uiso 0.307(12) 1 d PDU A 2 H13P H 0.2764 0.8052 0.2258 0.105 Uiso 0.307(12) 1 calc PR A 2 C14P C 0.463(5) 0.863(2) 0.2925(10) 0.12(2) Uiso 0.307(12) 1 d PD A 2 H14P H 0.3816 0.8529 0.3313 0.143 Uiso 0.307(12) 1 calc PR A 2 C15P C 0.399(4) 0.844(2) 0.1010(10) 0.074(5) Uiso 0.307(12) 1 d PDU A 2 C16P C 0.777(6) 0.648(2) 0.1010(12) 0.090(9) Uiso 0.307(12) 1 d PDU A 2 H16P H 0.8645 0.6021 0.0963 0.108 Uiso 0.307(12) 1 calc PR A 2 C17P C 0.768(5) 0.669(2) 0.1771(12) 0.10(2) Uiso 0.307(12) 1 d PD A 2 H17P H 0.7193 0.7222 0.1808 0.120 Uiso 0.307(12) 1 calc PR A 2 C18P C 0.991(4) 0.664(2) 0.2114(14) 0.110(10) Uiso 0.307(12) 1 d PDU A 2 H18C H 1.0914 0.6970 0.1879 0.132 Uiso 0.307(12) 1 calc PR A 2 H18D H 1.0443 0.6118 0.2073 0.132 Uiso 0.307(12) 1 calc PR A 2 C19P C 0.983(5) 0.686(2) 0.2873(15) 0.109(10) Uiso 0.307(12) 1 d PDU A 2 H19C H 1.1234 0.6760 0.3078 0.130 Uiso 0.307(12) 1 calc PR A 2 H19D H 0.9538 0.7400 0.2912 0.130 Uiso 0.307(12) 1 calc PR A 2 C20P C 0.812(6) 0.642(3) 0.3265(14) 0.190(10) Uiso 0.307(12) 1 d PDU A 2 H20C H 0.8551 0.5888 0.3304 0.228 Uiso 0.307(12) 1 calc PR A 2 H20D H 0.7989 0.6627 0.3722 0.228 Uiso 0.307(12) 1 calc PR A 2 C21P C 0.594(5) 0.646(3) 0.2909(15) 0.127(10) Uiso 0.307(12) 1 d PDU A 2 H21C H 0.5430 0.6987 0.2919 0.152 Uiso 0.307(12) 1 calc PR A 2 H21D H 0.4903 0.6152 0.3155 0.152 Uiso 0.307(12) 1 calc PR A 2 C22P C 0.607(5) 0.619(2) 0.2164(15) 0.103(9) Uiso 0.307(12) 1 d PDU A 2 H22C H 0.6543 0.5662 0.2150 0.124 Uiso 0.307(12) 1 calc PR A 2 H22D H 0.4656 0.6222 0.1952 0.124 Uiso 0.307(12) 1 calc PR A 2 C23P C 0.557(6) 0.633(3) 0.0676(17) 0.081(13) Uiso 0.307(12) 1 d PD A 2 H23D H 0.5785 0.6187 0.0208 0.122 Uiso 0.307(12) 1 calc PR A 2 H23E H 0.4702 0.6783 0.0698 0.122 Uiso 0.307(12) 1 calc PR A 2 H23F H 0.4857 0.5923 0.0915 0.122 Uiso 0.307(12) 1 calc PR A 2 O1P O 0.970(2) 0.9362(12) 0.3710(7) 0.091(6) Uiso 0.307(12) 1 d PDU A 2 O2P O 0.198(4) 0.8351(18) 0.0990(16) 0.100(11) Uiso 0.307(12) 1 d PDU A 2 O3P O 0.524(5) 0.815(3) 0.0561(17) 0.095(12) Uiso 0.307(12) 1 d PDU A 2 N1P N 0.886(7) 0.711(2) 0.0609(17) 0.065(12) Uiso 0.307(12) 1 d PD A 2 H1P1 H 0.9772 0.7361 0.0880 0.097 Uiso 0.307(12) 1 calc PR A 2 H1P2 H 0.7866 0.7432 0.0449 0.097 Uiso 0.307(12) 1 calc PR A 2 H1P3 H 0.9589 0.6907 0.0261 0.097 Uiso 0.307(12) 1 calc PR A 2 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 C1R 0.135(11) 0.150(11) 0.073(7) -0.021(8) -0.019(8) 0.012(10) C2R 0.144(13) 0.168(14) 0.162(15) 0.037(12) 0.009(11) -0.003(12) C3R 0.132(14) 0.19(2) 0.110(12) -0.024(13) -0.022(12) -0.028(15) C4R 0.20(2) 0.106(13) 0.21(2) -0.010(13) 0.041(17) 0.010(14) C5R 0.168(12) 0.140(12) 0.121(11) 0.020(10) 0.022(11) -0.010(11) C6R 0.133(11) 0.153(13) 0.107(9) -0.011(9) 0.016(8) 0.002(10) C7R 0.148(11) 0.119(10) 0.089(8) -0.026(7) 0.015(9) -0.001(11) C8R 0.105(9) 0.112(12) 0.144(12) 0.005(9) -0.021(9) 0.012(9) C9R 0.122(10) 0.069(8) 0.064(7) -0.016(5) -0.014(7) -0.015(8) C10R 0.080(7) 0.123(10) 0.084(8) -0.013(7) -0.019(6) -0.017(8) C11R 0.096(9) 0.119(13) 0.078(8) -0.026(7) -0.005(7) 0.015(9) C12R 0.067(10) 0.112(16) 0.081(12) -0.030(8) -0.003(6) 0.004(6) C13R 0.087(5) 0.078(7) 0.082(6) -0.027(5) 0.017(5) -0.008(6) C14R 0.108(11) 0.079(10) 0.078(8) -0.010(6) 0.024(7) 0.000(7) C15R 0.074(6) 0.071(7) 0.075(6) -0.008(5) -0.012(5) 0.017(5) C16R 0.100(8) 0.078(8) 0.081(7) -0.001(6) -0.004(6) -0.011(7) C17R 0.113(13) 0.102(14) 0.073(10) 0.021(7) -0.018(7) -0.014(8) C18R 0.113(9) 0.097(10) 0.086(7) 0.019(7) -0.008(7) -0.005(8) C19R 0.115(10) 0.144(12) 0.072(7) 0.005(7) 0.017(7) -0.012(10) C20R 0.226(15) 0.201(15) 0.113(10) 0.034(11) -0.050(12) -0.008(14) C21R 0.143(10) 0.142(13) 0.087(9) 0.036(9) 0.011(8) -0.018(10) C22R 0.118(9) 0.098(10) 0.118(10) 0.003(8) 0.036(8) -0.022(9) C23R 0.111(14) 0.119(14) 0.140(16) -0.042(11) -0.009(12) -0.022(13) O1R 0.205(13) 0.218(17) 0.155(11) -0.070(11) -0.021(10) -0.058(12) O2R 0.070(6) 0.122(10) 0.104(7) -0.012(7) -0.024(5) -0.014(6) O3R 0.083(6) 0.101(11) 0.053(5) -0.020(5) -0.013(4) -0.007(6) N1R 0.083(9) 0.104(12) 0.052(6) -0.021(7) 0.009(4) 0.004(8) _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 C1R C2R 1.508(9) . ? C1R C7R 1.539(9) . ? C1R C6R 1.556(9) . ? C2R C3R 1.322(9) . ? C3R C4R 1.525(10) . ? C4R C7R 1.563(9) . ? C4R C5R 1.564(9) . ? C5R C6R 1.561(9) . ? C7R C8R 1.498(8) . ? C8R O1R 1.237(9) . ? C8R C9R 1.486(8) . ? C9R C14R 1.396(9) . ? C9R C10R 1.398(8) . ? C10R C11R 1.379(8) . ? C11R C12R 1.403(9) . ? C12R C13R 1.382(8) . ? C12R C15R 1.511(8) . ? C13R C14R 1.381(8) . ? C15R O2R 1.241(8) . ? C15R O3R 1.276(8) . ? C16R N1R 1.508(9) . ? C16R C23R 1.525(9) . ? C16R C17R 1.541(9) . ? C17R C18R 1.533(9) . ? C17R C22R 1.537(9) . ? C18R C19R 1.536(9) . ? C19R C20R 1.519(10) . ? C20R C21R 1.514(9) . ? C21R C22R 1.519(9) . ? C1P C7P 1.504(10) . ? C1P C6P 1.521(10) . ? C1P C2P 1.553(10) . ? C2P O1P 1.470(10) . ? C2P C3P 1.502(10) . ? C3P C4P 1.327(10) . ? C4P C5P 1.498(10) . ? C5P C6P 1.521(10) . ? C7P C8P 1.326(9) . ? C8P O1P 1.380(9) . ? C8P C9P 1.521(8) . ? C9P C14P 1.390(9) . ? C9P C10P 1.402(9) . ? C10P C11P 1.386(9) . ? C11P C12P 1.397(9) . ? C12P C13P 1.390(9) . ? C12P C15P 1.520(9) . ? C13P C14P 1.386(10) . ? C15P O2P 1.249(10) . ? C15P O3P 1.274(10) . ? C16P N1P 1.509(10) . ? C16P C23P 1.527(10) . ? C16P C17P 1.535(10) . ? C17P C18P 1.533(10) . ? C17P C22P 1.534(10) . ? C18P C19P 1.536(10) . ? C19P C20P 1.516(10) . ? C20P C21P 1.515(10) . ? C21P C22P 1.538(10) . ? 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 C2R C1R C7R 102.8(8) . . ? C2R C1R C6R 101.4(10) . . ? C7R C1R C6R 100.5(8) . . ? C3R C2R C1R 108.3(9) . . ? C2R C3R C4R 107.8(9) . . ? C3R C4R C7R 101.7(8) . . ? C3R C4R C5R 103.1(10) . . ? C7R C4R C5R 98.8(8) . . ? C6R C5R C4R 102.9(7) . . ? C1R C6R C5R 103.1(7) . . ? C8R C7R C1R 112.4(8) . . ? C8R C7R C4R 113.3(9) . . ? C1R C7R C4R 93.7(7) . . ? O1R C8R C9R 117.9(9) . . ? O1R C8R C7R 121.8(9) . . ? C9R C8R C7R 119.8(8) . . ? C14R C9R C10R 117.6(7) . . ? C14R C9R C8R 124.0(8) . . ? C10R C9R C8R 118.2(8) . . ? C11R C10R C9R 120.5(9) . . ? C10R C11R C12R 120.5(9) . . ? C13R C12R C11R 119.0(8) . . ? C13R C12R C15R 120.5(8) . . ? C11R C12R C15R 119.3(8) . . ? C14R C13R C12R 119.6(8) . . ? C13R C14R C9R 121.9(8) . . ? O2R C15R O3R 123.5(9) . . ? O2R C15R C12R 120.0(8) . . ? O3R C15R C12R 115.9(8) . . ? N1R C16R C23R 108.3(10) . . ? N1R C16R C17R 110.0(8) . . ? C23R C16R C17R 114.5(11) . . ? C18R C17R C22R 110.6(10) . . ? C18R C17R C16R 109.8(9) . . ? C22R C17R C16R 111.0(9) . . ? C17R C18R C19R 112.7(9) . . ? C20R C19R C18R 111.3(10) . . ? C21R C20R C19R 113.2(10) . . ? C20R C21R C22R 114.2(10) . . ? C21R C22R C17R 110.9(9) . . ? C7P C1P C6P 112.3(14) . . ? C7P C1P C2P 100.4(10) . . ? C6P C1P C2P 112.6(12) . . ? O1P C2P C3P 109.5(14) . . ? O1P C2P C1P 104.5(9) . . ? C3P C2P C1P 112.4(11) . . ? C4P C3P C2P 123.8(14) . . ? C3P C4P C5P 122.9(13) . . ? C4P C5P C6P 111.5(12) . . ? C1P C6P C5P 114.2(13) . . ? C8P C7P C1P 107.0(10) . . ? C7P C8P O1P 116.2(9) . . ? C7P C8P C9P 127.0(11) . . ? O1P C8P C9P 116.9(10) . . ? C14P C9P C10P 119.7(10) . . ? C14P C9P C8P 121.8(12) . . ? C10P C9P C8P 118.5(11) . . ? C11P C10P C9P 120.2(12) . . ? C10P C11P C12P 119.7(12) . . ? C13P C12P C11P 119.6(11) . . ? C13P C12P C15P 118.8(12) . . ? C11P C12P C15P 121.4(12) . . ? C14P C13P C12P 120.2(12) . . ? C13P C14P C9P 119.8(12) . . ? O2P C15P O3P 122.5(16) . . ? O2P C15P C12P 116.6(14) . . ? O3P C15P C12P 117.5(15) . . ? N1P C16P C23P 107.7(14) . . ? N1P C16P C17P 110.3(14) . . ? C23P C16P C17P 115.3(15) . . ? C18P C17P C22P 109.0(14) . . ? C18P C17P C16P 112.4(14) . . ? C22P C17P C16P 111.8(13) . . ? C17P C18P C19P 112.3(13) . . ? C20P C19P C18P 112.5(14) . . ? C21P C20P C19P 111.2(15) . . ? C20P C21P C22P 111.9(15) . . ? C17P C22P C21P 109.3(13) . . ? C8P O1P C2P 104.2(9) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.363 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.104 #===END data_32.5%P _database_code_depnum_ccdc_archive 'CCDC 608927' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H31 N O3' _chemical_formula_weight 369.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.1916(13) _cell_length_b 17.515(4) _cell_length_c 19.583(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2123.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 14 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9596 _exptl_absorpt_correction_T_max 0.9777 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kuma KM4CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11480 _diffrn_reflns_av_R_equivalents 0.0823 _diffrn_reflns_av_sigmaI/netI 0.0792 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3722 _reflns_number_gt 1527 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CRYSALIS (Oxford Diffraction, 2003)' _computing_cell_refinement 'CRYSALIS (Oxford Diffraction, 2003)' _computing_data_reduction 'CRYSALIS (Oxford Diffraction, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997)' _computing_publication_material 'SHELXL97 (Sheldrick, 1997)' _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary geom _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ; The absolute configuration was assigned to agree with that from Xia W. et al., 2005 ; _refine_ls_number_reflns 3722 _refine_ls_number_parameters 353 _refine_ls_number_restraints 273 _refine_ls_R_factor_all 0.2394 _refine_ls_R_factor_gt 0.1630 _refine_ls_wR_factor_ref 0.4348 _refine_ls_wR_factor_gt 0.4032 _refine_ls_goodness_of_fit_ref 1.268 _refine_ls_restrained_S_all 1.276 _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 C1R C 0.817(3) 0.9753(8) 0.4857(6) 0.140(6) Uani 0.675(11) 1 d PDU A 1 H1R H 0.8078 1.0312 0.4854 0.168 Uiso 0.675(11) 1 calc PR A 1 C2R C 1.042(2) 0.9415(13) 0.4822(11) 0.174(8) Uani 0.675(11) 1 d PDU A 1 H2R H 1.1691 0.9658 0.4950 0.209 Uiso 0.675(11) 1 calc PR A 1 C3R C 1.026(3) 0.8710(13) 0.4577(12) 0.186(14) Uani 0.675(11) 1 d PD A 1 H3R H 1.1401 0.8386 0.4476 0.223 Uiso 0.675(11) 1 calc PR A 1 C4R C 0.787(3) 0.8525(7) 0.4490(8) 0.187(10) Uani 0.675(11) 1 d PD A 1 H4R H 0.7510 0.8093 0.4193 0.224 Uiso 0.675(11) 1 calc PR A 1 C5R C 0.698(3) 0.8499(9) 0.5237(9) 0.154(7) Uani 0.675(11) 1 d PDU A 1 H5R1 H 0.5487 0.8332 0.5244 0.185 Uiso 0.675(11) 1 calc PR A 1 H5R2 H 0.7835 0.8159 0.5520 0.185 Uiso 0.675(11) 1 calc PR A 1 C6R C 0.719(3) 0.9340(10) 0.5484(7) 0.134(6) Uani 0.675(11) 1 d PDU A 1 H6R1 H 0.5787 0.9551 0.5600 0.161 Uiso 0.675(11) 1 calc PR A 1 H6R2 H 0.8133 0.9377 0.5877 0.161 Uiso 0.675(11) 1 calc PR A 1 C7R C 0.700(3) 0.9328(9) 0.4271(5) 0.139(6) Uani 0.675(11) 1 d PDU A 1 H7R H 0.5423 0.9365 0.4309 0.166 Uiso 0.675(11) 1 calc PR A 1 C8R C 0.781(2) 0.9571(9) 0.3583(5) 0.132(6) Uani 0.675(11) 1 d PDU A 1 C9R C 0.684(2) 0.9240(7) 0.2956(5) 0.091(5) Uani 0.675(11) 1 d PD A 1 C10R C 0.813(2) 0.9178(12) 0.2373(6) 0.105(5) Uani 0.675(11) 1 d PDU A 1 H10R H 0.9576 0.9315 0.2391 0.126 Uiso 0.675(11) 1 calc PR A 1 C11R C 0.724(2) 0.8914(11) 0.1770(6) 0.098(5) Uani 0.675(11) 1 d PDU A 1 H11R H 0.8106 0.8877 0.1383 0.118 Uiso 0.675(11) 1 calc PR A 1 C12R C 0.506(2) 0.8700(13) 0.1728(6) 0.087(5) Uani 0.675(11) 1 d PDU A 1 C13R C 0.3883(19) 0.8668(8) 0.2328(6) 0.085(4) Uani 0.675(11) 1 d PDU A 1 H13R H 0.2499 0.8462 0.2326 0.102 Uiso 0.675(11) 1 calc PR A 1 C14R C 0.476(2) 0.8940(11) 0.2928(6) 0.095(5) Uani 0.675(11) 1 d PD A 1 H14R H 0.3932 0.8922 0.3325 0.114 Uiso 0.675(11) 1 calc PR A 1 C15R C 0.4217(18) 0.8317(10) 0.1088(6) 0.088(3) Uani 0.675(11) 1 d PDU A 1 C16R C 0.793(3) 0.6545(8) 0.0979(6) 0.089(4) Uani 0.675(11) 1 d PDU A 1 H16R H 0.9036 0.6145 0.0949 0.106 Uiso 0.675(11) 1 calc PR A 1 C17R C 0.739(3) 0.6681(10) 0.1738(6) 0.113(11) Uani 0.675(11) 1 d PD A 1 H17R H 0.6326 0.7094 0.1773 0.136 Uiso 0.675(11) 1 calc PR A 1 C18R C 0.944(2) 0.6912(9) 0.2124(6) 0.104(5) Uani 0.675(11) 1 d PDU A 1 H18A H 0.9995 0.7381 0.1928 0.125 Uiso 0.675(11) 1 calc PR A 1 H18B H 1.0524 0.6519 0.2059 0.125 Uiso 0.675(11) 1 calc PR A 1 C19R C 0.909(3) 0.7030(10) 0.2891(6) 0.113(5) Uani 0.675(11) 1 d PDU A 1 H19A H 1.0471 0.7116 0.3110 0.136 Uiso 0.675(11) 1 calc PR A 1 H19B H 0.8210 0.7483 0.2960 0.136 Uiso 0.675(11) 1 calc PR A 1 C20R C 0.799(4) 0.6356(15) 0.3224(9) 0.201(8) Uani 0.675(11) 1 d PDU A 1 H20A H 0.7548 0.6497 0.3682 0.241 Uiso 0.675(11) 1 calc PR A 1 H20B H 0.9018 0.5940 0.3262 0.241 Uiso 0.675(11) 1 calc PR A 1 C21R C 0.603(3) 0.6080(12) 0.2831(7) 0.139(7) Uani 0.675(11) 1 d PDU A 1 H21A H 0.4879 0.6452 0.2880 0.167 Uiso 0.675(11) 1 calc PR A 1 H21B H 0.5532 0.5604 0.3030 0.167 Uiso 0.675(11) 1 calc PR A 1 C22R C 0.646(3) 0.5954(9) 0.2072(7) 0.124(6) Uani 0.675(11) 1 d PDU A 1 H22A H 0.5119 0.5815 0.1846 0.149 Uiso 0.675(11) 1 calc PR A 1 H22B H 0.7468 0.5536 0.2016 0.149 Uiso 0.675(11) 1 calc PR A 1 C23R C 0.598(4) 0.6304(15) 0.0544(11) 0.122(8) Uani 0.675(11) 1 d PD A 1 H23A H 0.6454 0.6192 0.0088 0.182 Uiso 0.675(11) 1 calc PR A 1 H23B H 0.4947 0.6712 0.0533 0.182 Uiso 0.675(11) 1 calc PR A 1 H23C H 0.5330 0.5858 0.0740 0.182 Uiso 0.675(11) 1 calc PR A 1 O1R O 0.935(3) 1.0017(11) 0.3505(7) 0.191(6) Uani 0.675(11) 1 d PDU A 1 O2R O 0.2356(15) 0.8049(9) 0.1073(6) 0.106(4) Uani 0.675(11) 1 d PDU A 1 O3R O 0.5455(15) 0.8357(7) 0.0564(4) 0.078(3) Uani 0.675(11) 1 d PDU A 1 N1R N 0.881(2) 0.7263(8) 0.0664(5) 0.078(4) Uani 0.675(11) 1 d PDU A 1 H1R1 H 0.9056 0.7185 0.0221 0.118 Uiso 0.675(11) 1 calc PR A 1 H1R2 H 1.0044 0.7389 0.0869 0.118 Uiso 0.675(11) 1 calc PR A 1 H1R3 H 0.7860 0.7639 0.0714 0.118 Uiso 0.675(11) 1 calc PR A 1 C1P C 0.803(5) 0.9753(15) 0.4735(11) 0.143(9) Uiso 0.325(11) 1 d PDU A 2 H1P H 0.8020 1.0311 0.4702 0.172 Uiso 0.325(11) 1 calc PR A 2 C2P C 1.017(4) 0.9424(16) 0.4444(10) 0.161(12) Uiso 0.325(11) 1 d PDU A 2 H2P H 1.1346 0.9793 0.4504 0.194 Uiso 0.325(11) 1 calc PR A 2 C3P C 1.077(5) 0.867(2) 0.4755(16) 0.118(16) Uiso 0.325(11) 1 d PD A 2 H3P H 1.2084 0.8456 0.4630 0.142 Uiso 0.325(11) 1 calc PR A 2 C4P C 0.955(5) 0.8289(15) 0.5195(17) 0.127(12) Uiso 0.325(11) 1 d PD A 2 H4P H 0.9848 0.7774 0.5266 0.153 Uiso 0.325(11) 1 calc PR A 2 C5P C 0.773(6) 0.864(2) 0.5582(19) 0.147(11) Uiso 0.325(11) 1 d PDU A 2 H5P1 H 0.7926 0.8547 0.6065 0.176 Uiso 0.325(11) 1 calc PR A 2 H5P2 H 0.6385 0.8410 0.5441 0.176 Uiso 0.325(11) 1 calc PR A 2 C6P C 0.760(7) 0.9500(19) 0.5465(11) 0.128(9) Uiso 0.325(11) 1 d PDU A 2 H6P1 H 0.8633 0.9750 0.5763 0.154 Uiso 0.325(11) 1 calc PR A 2 H6P2 H 0.6170 0.9673 0.5597 0.154 Uiso 0.325(11) 1 calc PR A 2 C7P C 0.644(4) 0.941(3) 0.4239(12) 0.130(9) Uiso 0.325(11) 1 d PDU A 2 H7P H 0.4970 0.9333 0.4316 0.156 Uiso 0.325(11) 1 calc PR A 2 C8P C 0.751(3) 0.9245(19) 0.3672(10) 0.111(9) Uiso 0.325(11) 1 d PDU A 2 C9P C 0.655(3) 0.9006(13) 0.2990(10) 0.074(10) Uiso 0.325(11) 1 d PD A 2 C10P C 0.762(5) 0.922(2) 0.2390(11) 0.097(8) Uiso 0.325(11) 1 d PDU A 2 H10P H 0.8907 0.9494 0.2414 0.116 Uiso 0.325(11) 1 calc PR A 2 C11P C 0.676(6) 0.903(3) 0.1761(11) 0.101(9) Uiso 0.325(11) 1 d PDU A 2 H11P H 0.7425 0.9195 0.1363 0.121 Uiso 0.325(11) 1 calc PR A 2 C12P C 0.489(5) 0.858(2) 0.1718(9) 0.078(8) Uiso 0.325(11) 1 d PDU A 2 C13P C 0.390(4) 0.8337(17) 0.2317(10) 0.090(6) Uiso 0.325(11) 1 d PDU A 2 H13P H 0.2782 0.7985 0.2297 0.108 Uiso 0.325(11) 1 calc PR A 2 C14P C 0.459(4) 0.8618(19) 0.2943(10) 0.098(15) Uiso 0.325(11) 1 d PD A 2 H14P H 0.3746 0.8547 0.3331 0.117 Uiso 0.325(11) 1 calc PR A 2 C15P C 0.393(3) 0.838(2) 0.1029(11) 0.091(5) Uiso 0.325(11) 1 d PDU A 2 C16P C 0.781(6) 0.641(2) 0.1014(12) 0.100(9) Uiso 0.325(11) 1 d PDU A 2 H16P H 0.8798 0.5974 0.0982 0.120 Uiso 0.325(11) 1 calc PR A 2 C17P C 0.776(5) 0.666(2) 0.1766(12) 0.11(2) Uiso 0.325(11) 1 d PD A 2 H17P H 0.7383 0.7200 0.1785 0.130 Uiso 0.325(11) 1 calc PR A 2 C18P C 0.997(4) 0.655(2) 0.2106(13) 0.122(10) Uiso 0.325(11) 1 d PDU A 2 H18C H 1.0383 0.6014 0.2073 0.146 Uiso 0.325(11) 1 calc PR A 2 H18D H 1.1039 0.6846 0.1862 0.146 Uiso 0.325(11) 1 calc PR A 2 C19P C 0.997(5) 0.678(2) 0.2859(14) 0.112(10) Uiso 0.325(11) 1 d PDU A 2 H19C H 1.1342 0.6637 0.3061 0.135 Uiso 0.325(11) 1 calc PR A 2 H19D H 0.9868 0.7337 0.2885 0.135 Uiso 0.325(11) 1 calc PR A 2 C20P C 0.816(6) 0.644(3) 0.3272(14) 0.204(11) Uiso 0.325(11) 1 d PDU A 2 H20C H 0.8086 0.6693 0.3711 0.245 Uiso 0.325(11) 1 calc PR A 2 H20D H 0.8479 0.5904 0.3354 0.245 Uiso 0.325(11) 1 calc PR A 2 C21P C 0.600(5) 0.650(3) 0.2918(16) 0.147(11) Uiso 0.325(11) 1 d PDU A 2 H21C H 0.5546 0.7034 0.2917 0.176 Uiso 0.325(11) 1 calc PR A 2 H21D H 0.4932 0.6213 0.3172 0.176 Uiso 0.325(11) 1 calc PR A 2 C22P C 0.608(5) 0.621(2) 0.2179(15) 0.125(10) Uiso 0.325(11) 1 d PDU A 2 H22C H 0.6447 0.5671 0.2178 0.151 Uiso 0.325(11) 1 calc PR A 2 H22D H 0.4665 0.6265 0.1970 0.151 Uiso 0.325(11) 1 calc PR A 2 C23P C 0.567(7) 0.616(3) 0.069(2) 0.101(16) Uiso 0.325(11) 1 d PD A 2 H23D H 0.5905 0.6017 0.0227 0.152 Uiso 0.325(11) 1 calc PR A 2 H23E H 0.4658 0.6574 0.0715 0.152 Uiso 0.325(11) 1 calc PR A 2 H23F H 0.5107 0.5730 0.0942 0.152 Uiso 0.325(11) 1 calc PR A 2 O1P O 0.973(3) 0.9307(15) 0.3713(9) 0.125(7) Uiso 0.325(11) 1 d PDU A 2 O2P O 0.192(3) 0.8330(15) 0.0996(13) 0.088(7) Uiso 0.325(11) 1 d PDU A 2 O3P O 0.514(4) 0.8064(17) 0.0582(13) 0.102(8) Uiso 0.325(11) 1 d PDU A 2 N1P N 0.873(7) 0.703(2) 0.0574(16) 0.108(14) Uiso 0.325(11) 1 d PDU A 2 H1P1 H 0.9652 0.7312 0.0818 0.162 Uiso 0.325(11) 1 calc PR A 2 H1P2 H 0.7661 0.7332 0.0425 0.162 Uiso 0.325(11) 1 calc PR A 2 H1P3 H 0.9411 0.6830 0.0219 0.162 Uiso 0.325(11) 1 calc PR A 2 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 C1R 0.166(12) 0.178(13) 0.077(9) -0.018(9) -0.027(9) 0.038(12) C2R 0.158(14) 0.188(15) 0.175(16) 0.034(14) 0.012(13) 0.019(14) C3R 0.20(3) 0.23(3) 0.130(17) -0.058(19) -0.06(2) 0.02(2) C4R 0.20(2) 0.113(15) 0.25(3) -0.026(17) 0.03(2) 0.035(16) C5R 0.163(13) 0.158(14) 0.142(14) 0.017(12) 0.033(13) -0.014(12) C6R 0.134(12) 0.144(14) 0.124(11) 0.002(10) 0.034(10) 0.006(11) C7R 0.162(13) 0.126(12) 0.128(12) -0.034(10) 0.012(11) 0.016(12) C8R 0.132(12) 0.125(13) 0.138(12) 0.022(10) -0.004(10) -0.001(11) C9R 0.132(13) 0.073(9) 0.069(9) -0.012(7) -0.005(8) -0.037(10) C10R 0.077(8) 0.138(11) 0.100(10) -0.014(8) -0.012(8) -0.011(9) C11R 0.104(10) 0.104(11) 0.087(8) -0.037(7) 0.008(8) -0.002(10) C12R 0.064(7) 0.115(11) 0.081(8) -0.019(7) -0.011(6) -0.003(7) C13R 0.091(6) 0.080(8) 0.083(7) -0.029(6) 0.011(6) -0.001(6) C14R 0.116(14) 0.088(13) 0.082(10) -0.003(8) 0.016(8) 0.022(9) C15R 0.078(7) 0.090(7) 0.095(7) -0.015(6) -0.024(6) 0.019(6) C16R 0.120(9) 0.065(8) 0.081(8) 0.005(6) 0.002(7) -0.015(8) C17R 0.136(16) 0.117(16) 0.087(12) 0.034(9) -0.032(10) -0.042(12) C18R 0.120(10) 0.084(10) 0.108(9) 0.018(8) -0.011(8) -0.007(8) C19R 0.102(10) 0.164(13) 0.073(8) 0.000(9) 0.021(7) -0.002(10) C20R 0.234(17) 0.199(16) 0.169(15) 0.046(14) -0.021(16) -0.008(16) C21R 0.162(13) 0.157(15) 0.099(10) 0.031(10) -0.007(10) -0.027(12) C22R 0.139(11) 0.115(12) 0.119(11) -0.013(9) 0.035(9) -0.025(10) C23R 0.138(16) 0.103(15) 0.124(15) 0.002(12) -0.044(13) -0.051(11) O1R 0.206(12) 0.211(14) 0.157(10) -0.061(10) -0.027(10) -0.063(11) O2R 0.066(6) 0.142(11) 0.110(7) -0.018(7) -0.026(5) 0.004(6) O3R 0.081(5) 0.099(8) 0.055(4) -0.017(5) -0.004(4) -0.018(5) N1R 0.080(7) 0.103(10) 0.052(5) -0.028(6) 0.010(5) -0.004(7) _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 C1R C2R 1.512(9) . ? C1R C7R 1.549(9) . ? C1R C6R 1.550(9) . ? C2R C3R 1.328(10) . ? C3R C4R 1.520(10) . ? C4R C5R 1.563(9) . ? C4R C7R 1.567(9) . ? C5R C6R 1.555(10) . ? C7R C8R 1.501(9) . ? C8R O1R 1.241(9) . ? C8R C9R 1.484(8) . ? C9R C14R 1.395(9) . ? C9R C10R 1.396(9) . ? C10R C11R 1.383(9) . ? C11R C12R 1.403(9) . ? C12R C13R 1.383(8) . ? C12R C15R 1.514(8) . ? C13R C14R 1.379(9) . ? C15R O2R 1.245(8) . ? C15R O3R 1.283(8) . ? C16R N1R 1.503(9) . ? C16R C23R 1.536(9) . ? C16R C17R 1.543(9) . ? C17R C18R 1.531(10) . ? C17R C22R 1.545(9) . ? C18R C19R 1.532(9) . ? C19R C20R 1.511(10) . ? C20R C21R 1.517(10) . ? C21R C22R 1.524(10) . ? C1P C7P 1.507(10) . ? C1P C6P 1.521(10) . ? C1P C2P 1.554(10) . ? C2P O1P 1.471(10) . ? C2P C3P 1.501(10) . ? C3P C4P 1.324(10) . ? C4P C5P 1.495(10) . ? C5P C6P 1.518(10) . ? C7P C8P 1.326(9) . ? C8P O1P 1.383(9) . ? C8P C9P 1.520(8) . ? C9P C14P 1.391(9) . ? C9P C10P 1.402(9) . ? C10P C11P 1.386(9) . ? C11P C12P 1.396(9) . ? C12P C13P 1.390(9) . ? C12P C15P 1.519(9) . ? C13P C14P 1.389(10) . ? C15P O2P 1.245(10) . ? C15P O3P 1.276(10) . ? C16P N1P 1.505(10) . ? C16P C23P 1.527(10) . ? C16P C17P 1.536(10) . ? C17P C22P 1.535(10) . ? C17P C18P 1.536(10) . ? C18P C19P 1.531(10) . ? C19P C20P 1.510(10) . ? C20P C21P 1.514(10) . ? C21P C22P 1.537(10) . ? 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 C2R C1R C7R 102.1(9) . . ? C2R C1R C6R 102.4(10) . . ? C7R C1R C6R 100.2(8) . . ? C3R C2R C1R 108.1(9) . . ? C2R C3R C4R 108.2(9) . . ? C3R C4R C5R 104.1(11) . . ? C3R C4R C7R 100.0(9) . . ? C5R C4R C7R 99.2(8) . . ? C6R C5R C4R 103.5(7) . . ? C1R C6R C5R 103.2(7) . . ? C8R C7R C1R 111.8(9) . . ? C8R C7R C4R 112.6(10) . . ? C1R C7R C4R 93.8(7) . . ? O1R C8R C9R 117.1(9) . . ? O1R C8R C7R 123.1(10) . . ? C9R C8R C7R 119.8(9) . . ? C14R C9R C10R 117.8(8) . . ? C14R C9R C8R 123.7(9) . . ? C10R C9R C8R 118.4(9) . . ? C11R C10R C9R 119.9(9) . . ? C10R C11R C12R 121.4(9) . . ? C13R C12R C11R 117.9(8) . . ? C13R C12R C15R 120.2(8) . . ? C11R C12R C15R 119.8(8) . . ? C14R C13R C12R 120.3(9) . . ? C13R C14R C9R 121.8(9) . . ? O2R C15R O3R 123.7(9) . . ? O2R C15R C12R 120.4(8) . . ? O3R C15R C12R 115.6(8) . . ? N1R C16R C23R 106.7(10) . . ? N1R C16R C17R 110.2(8) . . ? C23R C16R C17R 114.0(11) . . ? C18R C17R C16R 109.6(10) . . ? C18R C17R C22R 108.6(10) . . ? C16R C17R C22R 111.2(10) . . ? C17R C18R C19R 113.7(9) . . ? C20R C19R C18R 112.4(11) . . ? C19R C20R C21R 112.9(12) . . ? C20R C21R C22R 113.7(12) . . ? C21R C22R C17R 111.0(9) . . ? C7P C1P C6P 112.1(14) . . ? C7P C1P C2P 100.1(10) . . ? C6P C1P C2P 112.7(12) . . ? O1P C2P C3P 108.5(14) . . ? O1P C2P C1P 104.5(9) . . ? C3P C2P C1P 112.8(11) . . ? C4P C3P C2P 124.6(13) . . ? C3P C4P C5P 123.2(13) . . ? C4P C5P C6P 112.2(12) . . ? C5P C6P C1P 114.8(13) . . ? C8P C7P C1P 107.4(10) . . ? C7P C8P O1P 115.6(10) . . ? C7P C8P C9P 126.8(11) . . ? O1P C8P C9P 117.6(11) . . ? C14P C9P C10P 119.2(10) . . ? C14P C9P C8P 122.3(12) . . ? C10P C9P C8P 118.4(11) . . ? C11P C10P C9P 119.8(12) . . ? C10P C11P C12P 120.6(12) . . ? C13P C12P C11P 119.0(10) . . ? C13P C12P C15P 120.2(12) . . ? C11P C12P C15P 120.8(12) . . ? C14P C13P C12P 120.1(12) . . ? C13P C14P C9P 119.9(12) . . ? O2P C15P O3P 121.6(16) . . ? O2P C15P C12P 116.9(13) . . ? O3P C15P C12P 118.6(15) . . ? N1P C16P C23P 107.6(14) . . ? N1P C16P C17P 110.5(15) . . ? C23P C16P C17P 117.1(15) . . ? C22P C17P C16P 112.1(13) . . ? C22P C17P C18P 108.1(14) . . ? C16P C17P C18P 111.3(14) . . ? C19P C18P C17P 112.7(13) . . ? C20P C19P C18P 113.9(15) . . ? C19P C20P C21P 112.5(15) . . ? C20P C21P C22P 112.2(15) . . ? C17P C22P C21P 110.3(13) . . ? C8P O1P C2P 104.6(9) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.431 _refine_diff_density_min -0.489 _refine_diff_density_rms 0.117 #===END