# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author_name 'Koichi Kodama' _publ_contact_author_email kodama@mail.saitama-u.ac.jp _publ_contact_author_address '255 Shimo-Okubo,Sakura-ku,Saitama,Japan' _publ_contact_author_fax +81-48-858-9548 _publ_contact_author_phone +81-48-858-9548 _publ_contact_letter ; ENTER TEXT OF LETTER ; #============================================================================== # TITLE AND AUTHOR LIST _publ_section_title ; Enantioseparation of 1-arylethanols via a supramolecular chiral host consisting of N-(2-naphthoyl)-L-aspartic acid and an achiral diamine ; _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; loop_ _publ_author_name _publ_author_footnote _publ_author_address ' Koichi Kodama ' ; Dept. of Applied Chemistry, Graduate School of Engineering, Saitama University ; ; 255 Shimo-Okubo,Sakura-ku,Saitama,Japan ; ; Ayaka Kanno ; ; Dept. of Applied Chemistry, Graduate School of Engineering, Saitama University ; ; 255 Shimo-Okubo,Sakura-ku,Saitama,Japan ; ; Eriko Sekine ; ; Dept. of Applied Chemistry, Graduate School of Engineering, Saitama University ; ; 255 Shimo-Okubo,Sakura-ku,Saitama,Japan ; ; Takuji Hirose ; ; Dept. of Applied Chemistry, Graduate School of Engineering, Saitama University ; ; 255 Shimo-Okubo,Sakura-ku,Saitama,Japan ; _publ_section_synopsis ; ENTER SYNOPSIS ; #===================================================================== data_L-1_2_(R)-3a _database_code_depnum_ccdc_archive 'CCDC 842304' #TrackingRef '- 1_2_3a.CIF' #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H39 N3 O6' _chemical_formula_weight 621.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.7098(9) _cell_length_b 9.5517(15) _cell_length_c 14.904(2) _cell_angle_alpha 87.425(2) _cell_angle_beta 89.606(2) _cell_angle_gamma 82.942(2) _cell_volume 805.9(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 330 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9576 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details ? _chemical_absolute_configuration rm _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3862 _diffrn_reflns_av_R_equivalents 0.1402 _diffrn_reflns_av_sigmaI/netI 0.0592 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3236 _reflns_number_gt 3180 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1323P)^2^+0.1505P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(12) _refine_ls_number_reflns 3236 _refine_ls_number_parameters 424 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1556 _refine_ls_wR_factor_gt 0.1544 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0185(4) -0.0334(2) 1.36683(16) 0.0178(5) Uani 1 1 d . . . O2 O -0.0464(4) -0.5880(2) 1.37295(16) 0.0190(5) Uani 1 1 d . . . O3 O 0.2718(4) -0.1626(2) 1.44452(16) 0.0193(5) Uani 1 1 d . . . N10 N 0.4308(5) 0.3746(3) 1.39473(19) 0.0171(6) Uani 1 1 d . . . H33 H 0.4690 0.4161 1.3319 0.026 Uiso 1 1 calc R . . H34 H 0.5099 0.4268 1.4432 0.026 Uiso 1 1 calc R . . H35 H 0.2503 0.3871 1.4044 0.026 Uiso 1 1 calc R . . O5 O -0.3165(4) -0.4762(2) 1.27863(17) 0.0218(5) Uani 1 1 d . . . N11 N 0.5043(5) -0.0035(3) 1.32882(18) 0.0155(6) Uani 1 1 d . . . H36 H 0.4691 -0.0470 1.3914 0.023 Uiso 1 1 calc R . . H37 H 0.6844 -0.0145 1.3182 0.023 Uiso 1 1 calc R . . H38 H 0.4246 -0.0550 1.2801 0.023 Uiso 1 1 calc R . . O6 O 0.2899(4) -0.1870(2) 1.21380(15) 0.0183(5) Uani 1 1 d . . . N8 N -0.0594(5) -0.2730(3) 1.23450(18) 0.0166(6) Uani 1 1 d . . . C47 C 0.0000(6) -0.1321(3) 1.0995(2) 0.0182(7) Uani 1 1 d . . . C10 C 0.0904(6) -0.1988(3) 1.1869(2) 0.0162(7) Uani 1 1 d . . . O7 O 0.4248(5) 0.5845(3) 1.52645(18) 0.0283(6) Uani 1 1 d . . . C12 C 0.0090(6) -0.3563(3) 1.3166(2) 0.0158(6) Uani 1 1 d . . . H1 H 0.1825 -0.3879 1.3159 0.019 Uiso 1 1 calc R . . C13 C 0.4580(6) 0.2184(3) 1.2327(2) 0.0173(7) Uani 1 1 d . . . C14 C 0.1263(6) -0.0327(3) 1.0583(2) 0.0200(7) Uani 1 1 d . . . H2 H 0.2689 -0.0136 1.0851 0.024 Uiso 1 1 calc R . . C15 C -0.0574(6) -0.2757(3) 1.4022(2) 0.0164(7) Uani 1 1 d . . . H3 H -0.2296 -0.2458 1.4031 0.020 Uiso 1 1 calc R . . H4 H -0.0169 -0.3389 1.4558 0.020 Uiso 1 1 calc R . . C16 C 0.6798(6) 0.1968(3) 1.1928(2) 0.0211(7) Uani 1 1 d . . . H5 H 0.8018 0.1330 1.2204 0.025 Uiso 1 1 calc R . . C17 C 0.4696(6) 0.1567(3) 1.4935(2) 0.0156(7) Uani 1 1 d . . . C18 C 0.6452(6) 0.0694(3) 1.5391(2) 0.0206(7) Uani 1 1 d . . . H6 H 0.7978 0.0509 1.5132 0.025 Uiso 1 1 calc R . . C19 C 0.2804(6) 0.3105(4) 1.1918(2) 0.0216(7) Uani 1 1 d . . . H7 H 0.1280 0.3240 1.2183 0.026 Uiso 1 1 calc R . . C20 C 0.0501(7) 0.0409(4) 0.9780(2) 0.0238(8) Uani 1 1 d . . . C21 C 0.5222(6) 0.2211(3) 1.4015(2) 0.0146(6) Uani 1 1 d . . . H8 H 0.6971 0.2105 1.3925 0.018 Uiso 1 1 calc R . . C22 C -0.1284(5) -0.4862(3) 1.3212(2) 0.0162(7) Uani 1 1 d . . . C23 C 0.0729(6) -0.1474(3) 1.4057(2) 0.0154(7) Uani 1 1 d . . . C24 C -0.2841(7) -0.0961(5) 0.9782(3) 0.0316(8) Uani 1 1 d . . . H9 H -0.4223 -0.1202 0.9507 0.038 Uiso 1 1 calc R . . C25 C -0.2082(6) -0.1637(4) 1.0566(2) 0.0254(8) Uani 1 1 d . . . H10 H -0.2953 -0.2332 1.0834 0.030 Uiso 1 1 calc R . . C26 C -0.1598(7) 0.0107(4) 0.9363(2) 0.0269(8) Uani 1 1 d . . . C27 C 0.7225(7) 0.2692(4) 1.1122(3) 0.0258(8) Uani 1 1 d . . . H11 H 0.8733 0.2544 1.0845 0.031 Uiso 1 1 calc R . . C28 C 0.3769(7) 0.0365(4) 1.6614(2) 0.0305(9) Uani 1 1 d . . . H12 H 0.3450 -0.0047 1.7187 0.037 Uiso 1 1 calc R . . C29 C 0.5979(7) 0.0080(4) 1.6238(3) 0.0272(8) Uani 1 1 d . . . H13 H 0.7176 -0.0528 1.6549 0.033 Uiso 1 1 calc R . . C30 C 0.4465(7) 0.6230(4) 1.6869(3) 0.0285(8) Uani 1 1 d . . . C31 C 0.1710(8) 0.1497(4) 0.9375(3) 0.0303(9) Uani 1 1 d . . . H14 H 0.3134 0.1708 0.9634 0.036 Uiso 1 1 calc R . . C32 C 0.5834(7) 0.5931(4) 1.6000(2) 0.0257(8) Uani 1 1 d . . . H15 H 0.6776 0.6729 1.5860 0.031 Uiso 1 1 calc R . . C33 C 0.3257(7) 0.3839(4) 1.1112(3) 0.0289(8) Uani 1 1 d . . . H16 H 0.2049 0.4484 1.0834 0.035 Uiso 1 1 calc R . . C34 C 0.5453(8) 0.3622(4) 1.0727(3) 0.0310(9) Uani 1 1 d . . . H17 H 0.5757 0.4119 1.0180 0.037 Uiso 1 1 calc R . . C35 C 0.4094(5) 0.1504(3) 1.3241(2) 0.0134(6) Uani 1 1 d . . . H18 H 0.2348 0.1594 1.3337 0.016 Uiso 1 1 calc R . . C36 C -0.2423(8) 0.0889(5) 0.8579(3) 0.0375(10) Uani 1 1 d . . . H19 H -0.3816 0.0679 0.8296 0.045 Uiso 1 1 calc R . . C37 C 0.2457(6) 0.1841(4) 1.5317(2) 0.0230(7) Uani 1 1 d . . . H20 H 0.1244 0.2431 1.5002 0.028 Uiso 1 1 calc R . . C38 C 0.7495(8) 0.4577(4) 1.6040(3) 0.0326(9) Uani 1 1 d . . . H21 H 0.6614 0.3786 1.6207 0.049 Uiso 1 1 calc R . . H22 H 0.8720 0.4637 1.6489 0.049 Uiso 1 1 calc R . . H23 H 0.8231 0.4428 1.5451 0.049 Uiso 1 1 calc R . . C39 C 0.2212(8) 0.6927(5) 1.6870(3) 0.0393(10) Uani 1 1 d . . . H24 H 0.1424 0.7157 1.6314 0.047 Uiso 1 1 calc R . . C40 C 0.0846(8) 0.2239(5) 0.8621(3) 0.0368(10) Uani 1 1 d . . . H25 H 0.1671 0.2964 0.8365 0.044 Uiso 1 1 calc R . . C41 C 0.2007(7) 0.1248(5) 1.6163(3) 0.0304(8) Uani 1 1 d . . . H26 H 0.0495 0.1448 1.6430 0.037 Uiso 1 1 calc R . . C42 C 0.5596(10) 0.5922(5) 1.7694(3) 0.0494(12) Uani 1 1 d . . . H27 H 0.7174 0.5471 1.7714 0.059 Uiso 1 1 calc R . . C43 C -0.1246(8) 0.1947(5) 0.8219(3) 0.0387(11) Uani 1 1 d . . . H28 H -0.1841 0.2481 0.7698 0.046 Uiso 1 1 calc R . . C44 C 0.1040(10) 0.7310(6) 1.7669(4) 0.0564(14) Uani 1 1 d . . . H29 H -0.0495 0.7823 1.7648 0.068 Uiso 1 1 calc R . . C45 C 0.2108(10) 0.6945(5) 1.8478(3) 0.0495(13) Uani 1 1 d . . . H30 H 0.1283 0.7147 1.9021 0.059 Uiso 1 1 calc R . . C46 C 0.4396(13) 0.6281(6) 1.8499(3) 0.0627(17) Uani 1 1 d . . . H31 H 0.5169 0.6063 1.9059 0.075 Uiso 1 1 calc R . . H32 H -0.204(14) -0.283(8) 1.217(5) 0.08(2) Uiso 1 1 d . . . H39 H 0.364(11) 0.655(7) 1.505(4) 0.054(17) 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 O1 0.0254(12) 0.0102(11) 0.0190(12) 0.0002(9) -0.0005(9) -0.0065(9) O2 0.0237(12) 0.0095(10) 0.0248(13) 0.0028(9) -0.0010(10) -0.0071(9) O3 0.0278(13) 0.0126(11) 0.0192(12) 0.0014(9) -0.0026(10) -0.0097(9) N10 0.0258(14) 0.0070(13) 0.0202(14) -0.0009(11) -0.0018(11) -0.0085(10) O5 0.0267(13) 0.0157(11) 0.0246(13) 0.0034(9) -0.0054(10) -0.0110(9) N11 0.0242(14) 0.0049(12) 0.0192(14) -0.0015(10) -0.0021(11) -0.0080(10) O6 0.0262(12) 0.0146(11) 0.0158(11) -0.0011(8) 0.0011(9) -0.0095(8) N8 0.0261(15) 0.0122(12) 0.0131(13) 0.0019(10) -0.0018(11) -0.0093(10) C47 0.0273(17) 0.0134(15) 0.0151(16) -0.0049(12) 0.0016(13) -0.0064(12) C10 0.0241(17) 0.0085(14) 0.0174(17) -0.0036(12) 0.0011(12) -0.0060(11) O7 0.0502(17) 0.0148(12) 0.0195(13) -0.0032(10) -0.0102(11) -0.0007(11) C12 0.0235(16) 0.0095(14) 0.0155(16) 0.0009(12) -0.0011(12) -0.0067(12) C13 0.0285(18) 0.0110(14) 0.0147(16) -0.0014(12) -0.0030(13) -0.0111(13) C14 0.0273(17) 0.0174(16) 0.0161(16) -0.0025(13) 0.0007(13) -0.0056(13) C15 0.0241(16) 0.0093(14) 0.0168(15) 0.0017(12) 0.0014(12) -0.0065(12) C16 0.0308(19) 0.0144(16) 0.0197(17) -0.0017(13) 0.0011(14) -0.0086(13) C17 0.0258(17) 0.0087(14) 0.0148(16) -0.0044(12) 0.0006(12) -0.0103(12) C18 0.0282(18) 0.0173(16) 0.0181(17) -0.0041(13) -0.0015(13) -0.0087(13) C19 0.0304(18) 0.0181(17) 0.0173(17) 0.0001(14) -0.0021(14) -0.0078(14) C20 0.0357(19) 0.0218(17) 0.0136(16) -0.0016(13) 0.0071(14) -0.0023(14) C21 0.0220(15) 0.0057(14) 0.0173(16) -0.0004(12) -0.0017(12) -0.0057(11) C22 0.0237(17) 0.0066(14) 0.0196(16) -0.0030(12) 0.0013(13) -0.0062(12) C23 0.0241(16) 0.0123(15) 0.0105(15) -0.0006(12) 0.0031(12) -0.0056(12) C24 0.034(2) 0.043(2) 0.0205(18) -0.0049(16) -0.0008(15) -0.0123(16) C25 0.0296(18) 0.0297(19) 0.0195(18) 0.0009(14) -0.0008(14) -0.0148(14) C26 0.0323(18) 0.033(2) 0.0148(17) -0.0002(14) 0.0020(13) -0.0004(15) C27 0.0356(19) 0.0238(18) 0.0207(18) -0.0034(14) 0.0075(15) -0.0134(15) C28 0.044(2) 0.038(2) 0.0134(17) 0.0028(15) -0.0004(15) -0.0218(17) C29 0.041(2) 0.0227(18) 0.0190(18) 0.0024(14) -0.0057(15) -0.0091(15) C30 0.048(2) 0.0165(16) 0.0220(19) -0.0033(14) -0.0012(16) -0.0064(15) C31 0.046(2) 0.0228(18) 0.023(2) 0.0059(15) 0.0058(16) -0.0073(16) C32 0.039(2) 0.0206(17) 0.0184(18) -0.0015(13) -0.0030(14) -0.0090(14) C33 0.045(2) 0.0208(19) 0.0206(19) 0.0055(14) -0.0064(15) -0.0038(16) C34 0.050(2) 0.0262(19) 0.0188(18) 0.0048(15) 0.0001(16) -0.0159(17) C35 0.0214(15) 0.0052(14) 0.0152(15) -0.0027(11) 0.0003(12) -0.0073(11) C36 0.038(2) 0.054(3) 0.0178(19) 0.0014(18) -0.0008(16) 0.0050(19) C37 0.0295(19) 0.0228(17) 0.0183(17) 0.0004(14) -0.0011(14) -0.0102(14) C38 0.045(2) 0.029(2) 0.0237(19) -0.0014(15) -0.0033(16) -0.0008(17) C39 0.044(2) 0.050(3) 0.023(2) -0.0010(18) 0.0017(17) -0.0031(19) C40 0.056(3) 0.033(2) 0.020(2) 0.0084(16) 0.0096(18) -0.0022(19) C41 0.0320(19) 0.043(2) 0.0196(18) -0.0026(16) 0.0048(14) -0.0162(16) C42 0.072(3) 0.045(3) 0.027(2) -0.0032(19) -0.002(2) 0.013(2) C43 0.047(2) 0.049(3) 0.016(2) 0.0101(18) 0.0052(17) 0.009(2) C44 0.052(3) 0.071(4) 0.043(3) -0.002(3) 0.019(2) 0.006(3) C45 0.082(4) 0.036(2) 0.029(2) -0.0014(18) 0.016(2) -0.005(2) C46 0.111(5) 0.050(3) 0.022(2) -0.001(2) -0.001(3) 0.011(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 O1 C23 1.265(4) . ? O2 C22 1.259(4) . ? O3 C23 1.268(4) . ? N10 C21 1.494(4) . ? N10 H33 1.0330 . ? N10 H34 1.0330 . ? N10 H35 1.0330 . ? O5 C22 1.243(4) . ? N11 C35 1.502(4) . ? N11 H36 1.0330 . ? N11 H37 1.0330 . ? N11 H38 1.0330 . ? O6 C10 1.230(4) . ? N8 C10 1.354(4) . ? N8 C12 1.457(4) . ? N8 H32 0.88(8) . ? C47 C14 1.381(5) . ? C47 C25 1.424(5) . ? C47 C10 1.491(5) . ? O7 C32 1.438(5) . ? O7 H39 0.77(6) . ? C12 C15 1.541(4) . ? C12 C22 1.546(4) . ? C12 H1 1.0000 . ? C13 C19 1.384(5) . ? C13 C16 1.392(5) . ? C13 C35 1.520(4) . ? C14 C20 1.405(5) . ? C14 H2 0.9500 . ? C15 C23 1.513(4) . ? C15 H3 0.9900 . ? C15 H4 0.9900 . ? C16 C27 1.395(5) . ? C16 H5 0.9500 . ? C17 C18 1.385(5) . ? C17 C37 1.396(5) . ? C17 C21 1.521(4) . ? C18 C29 1.406(5) . ? C18 H6 0.9500 . ? C19 C33 1.402(5) . ? C19 H7 0.9500 . ? C20 C26 1.420(6) . ? C20 C31 1.427(5) . ? C21 C35 1.546(4) . ? C21 H8 1.0000 . ? C24 C25 1.356(5) . ? C24 C26 1.432(5) . ? C24 H9 0.9500 . ? C25 H10 0.9500 . ? C26 C36 1.409(5) . ? C27 C34 1.378(6) . ? C27 H11 0.9500 . ? C28 C29 1.379(6) . ? C28 C41 1.388(6) . ? C28 H12 0.9500 . ? C29 H13 0.9500 . ? C30 C39 1.374(6) . ? C30 C42 1.395(6) . ? C30 C32 1.528(5) . ? C31 C40 1.363(6) . ? C31 H14 0.9500 . ? C32 C38 1.505(5) . ? C32 H15 1.0000 . ? C33 C34 1.372(6) . ? C33 H16 0.9500 . ? C34 H17 0.9500 . ? C35 H18 1.0000 . ? C36 C43 1.369(7) . ? C36 H19 0.9500 . ? C37 C41 1.394(5) . ? C37 H20 0.9500 . ? C38 H21 0.9800 . ? C38 H22 0.9800 . ? C38 H23 0.9800 . ? C39 C44 1.402(6) . ? C39 H24 0.9500 . ? C40 C43 1.404(7) . ? C40 H25 0.9500 . ? C41 H26 0.9500 . ? C42 C46 1.412(7) . ? C42 H27 0.9500 . ? C43 H28 0.9500 . ? C44 C45 1.366(8) . ? C44 H29 0.9500 . ? C45 C46 1.380(9) . ? C45 H30 0.9500 . ? C46 H31 0.9500 . ? 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 C21 N10 H33 109.5 . . ? C21 N10 H34 109.5 . . ? H33 N10 H34 109.5 . . ? C21 N10 H35 109.5 . . ? H33 N10 H35 109.5 . . ? H34 N10 H35 109.5 . . ? C35 N11 H36 109.5 . . ? C35 N11 H37 109.5 . . ? H36 N11 H37 109.5 . . ? C35 N11 H38 109.5 . . ? H36 N11 H38 109.5 . . ? H37 N11 H38 109.5 . . ? C10 N8 C12 123.1(3) . . ? C10 N8 H32 125(5) . . ? C12 N8 H32 112(4) . . ? C14 C47 C25 118.3(3) . . ? C14 C47 C10 117.5(3) . . ? C25 C47 C10 124.2(3) . . ? O6 C10 N8 122.2(3) . . ? O6 C10 C47 121.7(3) . . ? N8 C10 C47 116.1(3) . . ? C32 O7 H39 117(5) . . ? N8 C12 C15 112.9(2) . . ? N8 C12 C22 108.2(3) . . ? C15 C12 C22 106.1(2) . . ? N8 C12 H1 109.8 . . ? C15 C12 H1 109.8 . . ? C22 C12 H1 109.8 . . ? C19 C13 C16 119.8(3) . . ? C19 C13 C35 118.5(3) . . ? C16 C13 C35 121.5(3) . . ? C47 C14 C20 121.9(3) . . ? C47 C14 H2 119.0 . . ? C20 C14 H2 119.0 . . ? C23 C15 C12 110.6(2) . . ? C23 C15 H3 109.5 . . ? C12 C15 H3 109.5 . . ? C23 C15 H4 109.5 . . ? C12 C15 H4 109.5 . . ? H3 C15 H4 108.1 . . ? C13 C16 C27 119.8(3) . . ? C13 C16 H5 120.1 . . ? C27 C16 H5 120.1 . . ? C18 C17 C37 120.0(3) . . ? C18 C17 C21 119.5(3) . . ? C37 C17 C21 120.5(3) . . ? C17 C18 C29 120.0(3) . . ? C17 C18 H6 120.0 . . ? C29 C18 H6 120.0 . . ? C13 C19 C33 120.0(3) . . ? C13 C19 H7 120.0 . . ? C33 C19 H7 120.0 . . ? C14 C20 C26 119.5(3) . . ? C14 C20 C31 122.5(4) . . ? C26 C20 C31 117.9(3) . . ? N10 C21 C17 110.9(3) . . ? N10 C21 C35 107.1(2) . . ? C17 C21 C35 112.9(2) . . ? N10 C21 H8 108.6 . . ? C17 C21 H8 108.6 . . ? C35 C21 H8 108.6 . . ? O5 C22 O2 126.4(3) . . ? O5 C22 C12 117.0(3) . . ? O2 C22 C12 116.4(3) . . ? O1 C23 O3 124.1(3) . . ? O1 C23 C15 118.2(3) . . ? O3 C23 C15 117.6(3) . . ? C25 C24 C26 121.3(4) . . ? C25 C24 H9 119.4 . . ? C26 C24 H9 119.4 . . ? C24 C25 C47 121.1(3) . . ? C24 C25 H10 119.4 . . ? C47 C25 H10 119.4 . . ? C36 C26 C20 119.6(4) . . ? C36 C26 C24 122.6(4) . . ? C20 C26 C24 117.8(3) . . ? C34 C27 C16 119.9(3) . . ? C34 C27 H11 120.1 . . ? C16 C27 H11 120.1 . . ? C29 C28 C41 120.5(3) . . ? C29 C28 H12 119.7 . . ? C41 C28 H12 119.7 . . ? C28 C29 C18 119.7(4) . . ? C28 C29 H13 120.1 . . ? C18 C29 H13 120.1 . . ? C39 C30 C42 117.9(4) . . ? C39 C30 C32 122.2(4) . . ? C42 C30 C32 119.6(4) . . ? C40 C31 C20 120.8(4) . . ? C40 C31 H14 119.6 . . ? C20 C31 H14 119.6 . . ? O7 C32 C38 106.9(3) . . ? O7 C32 C30 110.8(3) . . ? C38 C32 C30 114.2(3) . . ? O7 C32 H15 108.3 . . ? C38 C32 H15 108.3 . . ? C30 C32 H15 108.3 . . ? C34 C33 C19 119.6(3) . . ? C34 C33 H16 120.2 . . ? C19 C33 H16 120.2 . . ? C33 C34 C27 120.9(3) . . ? C33 C34 H17 119.5 . . ? C27 C34 H17 119.5 . . ? N11 C35 C13 111.1(2) . . ? N11 C35 C21 107.6(2) . . ? C13 C35 C21 112.3(2) . . ? N11 C35 H18 108.6 . . ? C13 C35 H18 108.6 . . ? C21 C35 H18 108.6 . . ? C43 C36 C26 121.0(4) . . ? C43 C36 H19 119.5 . . ? C26 C36 H19 119.5 . . ? C41 C37 C17 119.8(4) . . ? C41 C37 H20 120.1 . . ? C17 C37 H20 120.1 . . ? C32 C38 H21 109.5 . . ? C32 C38 H22 109.5 . . ? H21 C38 H22 109.5 . . ? C32 C38 H23 109.5 . . ? H21 C38 H23 109.5 . . ? H22 C38 H23 109.5 . . ? C30 C39 C44 122.0(4) . . ? C30 C39 H24 119.0 . . ? C44 C39 H24 119.0 . . ? C31 C40 C43 121.0(4) . . ? C31 C40 H25 119.5 . . ? C43 C40 H25 119.5 . . ? C28 C41 C37 120.0(4) . . ? C28 C41 H26 120.0 . . ? C37 C41 H26 120.0 . . ? C30 C42 C46 120.1(5) . . ? C30 C42 H27 120.0 . . ? C46 C42 H27 120.0 . . ? C36 C43 C40 119.7(4) . . ? C36 C43 H28 120.1 . . ? C40 C43 H28 120.1 . . ? C45 C44 C39 119.9(5) . . ? C45 C44 H29 120.0 . . ? C39 C44 H29 120.0 . . ? C44 C45 C46 119.5(5) . . ? C44 C45 H30 120.3 . . ? C46 C45 H30 120.3 . . ? C45 C46 C42 120.5(5) . . ? C45 C46 H31 119.7 . . ? C42 C46 H31 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C12 N8 C10 O6 -6.2(5) . . . . ? C12 N8 C10 C47 173.7(3) . . . . ? C14 C47 C10 O6 -13.1(4) . . . . ? C25 C47 C10 O6 167.3(3) . . . . ? C14 C47 C10 N8 167.0(3) . . . . ? C25 C47 C10 N8 -12.6(5) . . . . ? C10 N8 C12 C15 96.0(3) . . . . ? C10 N8 C12 C22 -146.9(3) . . . . ? C25 C47 C14 C20 2.5(5) . . . . ? C10 C47 C14 C20 -177.1(3) . . . . ? N8 C12 C15 C23 -63.0(3) . . . . ? C22 C12 C15 C23 178.6(3) . . . . ? C19 C13 C16 C27 0.6(5) . . . . ? C35 C13 C16 C27 -175.2(3) . . . . ? C37 C17 C18 C29 0.2(5) . . . . ? C21 C17 C18 C29 -179.3(3) . . . . ? C16 C13 C19 C33 -1.2(5) . . . . ? C35 C13 C19 C33 174.7(3) . . . . ? C47 C14 C20 C26 -1.5(5) . . . . ? C47 C14 C20 C31 176.2(3) . . . . ? C18 C17 C21 N10 -134.2(3) . . . . ? C37 C17 C21 N10 46.3(4) . . . . ? C18 C17 C21 C35 105.7(3) . . . . ? C37 C17 C21 C35 -73.8(4) . . . . ? N8 C12 C22 O5 -23.7(4) . . . . ? C15 C12 C22 O5 97.7(3) . . . . ? N8 C12 C22 O2 161.1(3) . . . . ? C15 C12 C22 O2 -77.5(3) . . . . ? C12 C15 C23 O1 86.8(3) . . . . ? C12 C15 C23 O3 -90.4(3) . . . . ? C26 C24 C25 C47 -0.8(6) . . . . ? C14 C47 C25 C24 -1.4(5) . . . . ? C10 C47 C25 C24 178.2(3) . . . . ? C14 C20 C26 C36 177.1(3) . . . . ? C31 C20 C26 C36 -0.6(5) . . . . ? C14 C20 C26 C24 -0.7(5) . . . . ? C31 C20 C26 C24 -178.5(3) . . . . ? C25 C24 C26 C36 -175.9(4) . . . . ? C25 C24 C26 C20 1.9(6) . . . . ? C13 C16 C27 C34 0.3(6) . . . . ? C41 C28 C29 C18 0.2(6) . . . . ? C17 C18 C29 C28 -0.7(6) . . . . ? C14 C20 C31 C40 -176.5(4) . . . . ? C26 C20 C31 C40 1.2(5) . . . . ? C39 C30 C32 O7 -26.7(5) . . . . ? C42 C30 C32 O7 160.0(4) . . . . ? C39 C30 C32 C38 -147.5(4) . . . . ? C42 C30 C32 C38 39.3(5) . . . . ? C13 C19 C33 C34 1.0(6) . . . . ? C19 C33 C34 C27 -0.1(6) . . . . ? C16 C27 C34 C33 -0.6(6) . . . . ? C19 C13 C35 N11 137.1(3) . . . . ? C16 C13 C35 N11 -47.0(4) . . . . ? C19 C13 C35 C21 -102.4(3) . . . . ? C16 C13 C35 C21 73.5(4) . . . . ? N10 C21 C35 N11 178.7(3) . . . . ? C17 C21 C35 N11 -59.0(3) . . . . ? N10 C21 C35 C13 56.2(3) . . . . ? C17 C21 C35 C13 178.5(3) . . . . ? C20 C26 C36 C43 -0.8(6) . . . . ? C24 C26 C36 C43 177.0(4) . . . . ? C18 C17 C37 C41 0.8(5) . . . . ? C21 C17 C37 C41 -179.7(3) . . . . ? C42 C30 C39 C44 -0.9(7) . . . . ? C32 C30 C39 C44 -174.2(4) . . . . ? C20 C31 C40 C43 -0.5(6) . . . . ? C29 C28 C41 C37 0.8(6) . . . . ? C17 C37 C41 C28 -1.3(6) . . . . ? C39 C30 C42 C46 2.2(7) . . . . ? C32 C30 C42 C46 175.8(5) . . . . ? C26 C36 C43 C40 1.5(6) . . . . ? C31 C40 C43 C36 -0.9(6) . . . . ? C30 C39 C44 C45 -2.4(8) . . . . ? C39 C44 C45 C46 4.2(9) . . . . ? C44 C45 C46 C42 -2.8(9) . . . . ? C30 C42 C46 C45 -0.4(9) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.475 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.076 _publ_section_title_footnote ; ENTER FOOTNOTE TO TITLE OF PAPER ; _publ_section_synopsis ; ENTER SYNOPSIS ; #===================================================================== data_L-1_2_(R)-3e _database_code_depnum_ccdc_archive 'CCDC 842305' #TrackingRef '- 1_2_3e.CIF' #===================================================================== _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H41 N3 O6' _chemical_formula_weight 635.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.660(2) _cell_length_b 9.583(4) _cell_length_c 15.456(6) _cell_angle_alpha 94.113(5) _cell_angle_beta 92.683(5) _cell_angle_gamma 96.361(5) _cell_volume 829.8(5) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 338 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9581 _exptl_absorpt_correction_T_max 0.9957 _exptl_absorpt_process_details ? _chemical_absolute_configuration rm _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type CCD _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3764 _diffrn_reflns_av_R_equivalents 0.1348 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3208 _reflns_number_gt 2902 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1254P)^2^+2.9085P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(3) _refine_ls_number_reflns 3208 _refine_ls_number_parameters 434 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0972 _refine_ls_R_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.2513 _refine_ls_wR_factor_gt 0.2314 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.7736(9) 1.0271(5) 0.3484(4) 0.0213(12) Uani 1 1 d . . . O2 O 0.4739(9) 0.8934(6) 0.2735(4) 0.0218(12) Uani 1 1 d . . . O3 O 0.4862(9) 0.8880(5) 0.5001(3) 0.0213(12) Uani 1 1 d . . . O4 O 0.7976(10) 0.4739(5) 0.3503(4) 0.0249(13) Uani 1 1 d . . . O5 O 0.2929(11) 0.6347(7) 1.2032(4) 0.0306(14) Uani 1 1 d . . . N11 N 0.8353(12) 0.8014(7) 0.4801(4) 0.0227(15) Uani 1 1 d . . . O6 O 1.0806(9) 0.5898(6) 0.4411(4) 0.0260(13) Uani 1 1 d . . . N8 N 0.3160(11) 1.4349(6) 0.3288(4) 0.0200(14) Uani 1 1 d . . . H35 H 0.2810 1.4772 0.3896 0.030 Uiso 1 1 calc R . . H36 H 0.2328 1.4864 0.2817 0.030 Uiso 1 1 calc R . . H37 H 0.4975 1.4467 0.3217 0.030 Uiso 1 1 calc R . . C48 C 0.6887(12) 0.8736(7) 0.5254(5) 0.0171(15) Uani 1 1 d . . . C10 C 0.8890(13) 0.5799(8) 0.4005(5) 0.0211(17) Uani 1 1 d . . . C11 C 0.6767(13) 0.9108(7) 0.3120(5) 0.0177(16) Uani 1 1 d . . . C12 C 0.4956(15) 1.3732(9) 0.5213(6) 0.0265(19) Uani 1 1 d . . . H1 H 0.6442 1.3882 0.4953 0.032 Uiso 1 1 calc R . . N10 N 0.2580(11) 1.0587(6) 0.3847(4) 0.0180(13) Uani 1 1 d . . . H38 H 0.2873 1.0160 0.3234 0.027 Uiso 1 1 calc R . . H39 H 0.0776 1.0470 0.3941 0.027 Uiso 1 1 calc R . . H40 H 0.3455 1.0071 0.4307 0.027 Uiso 1 1 calc R . . C14 C 0.4907(15) 1.2458(10) 0.1929(6) 0.029(2) Uani 1 1 d . . . H2 H 0.6134 1.3088 0.2233 0.035 Uiso 1 1 calc R . . C15 C 0.7530(13) 0.7099(8) 0.4013(5) 0.0178(16) Uani 1 1 d . . . H3 H 0.5779 0.6807 0.4018 0.021 Uiso 1 1 calc R . . C16 C 0.0982(14) 1.2553(8) 0.5206(5) 0.0205(17) Uani 1 1 d . . . H4 H -0.0273 1.1902 0.4938 0.025 Uiso 1 1 calc R . . C17 C 0.3129(13) 1.2802(8) 0.4807(5) 0.0183(16) Uani 1 1 d . . . C18 C 0.2235(14) 1.2802(8) 0.3193(5) 0.0196(17) Uani 1 1 d . . . H5 H 0.0479 1.2688 0.3262 0.024 Uiso 1 1 calc R . . C19 C 0.2752(14) 1.2169(8) 0.2298(5) 0.0224(18) Uani 1 1 d . . . C20 C 0.3498(13) 1.2113(8) 0.3932(5) 0.0174(16) Uani 1 1 d . . . H6 H 0.5244 1.2207 0.3841 0.021 Uiso 1 1 calc R . . C21 C 0.0990(15) 1.1238(9) 0.1834(5) 0.0248(18) Uani 1 1 d . . . H7 H -0.0528 1.1052 0.2065 0.030 Uiso 1 1 calc R . . C22 C 0.6613(14) 1.0353(9) 0.6537(6) 0.0264(18) Uani 1 1 d . . . H8 H 0.5159 1.0562 0.6271 0.032 Uiso 1 1 calc R . . C23 C 0.2716(17) 0.6571(9) 1.0485(6) 0.035(2) Uani 1 1 d . . . C24 C 0.7919(13) 0.9421(8) 0.6120(5) 0.0204(16) Uani 1 1 d . . . C25 C 0.7437(15) 1.1023(9) 0.7384(5) 0.0284(19) Uani 1 1 d . . . C26 C 0.0698(17) 1.3271(10) 0.6003(6) 0.033(2) Uani 1 1 d . . . H9 H -0.0760 1.3099 0.6278 0.040 Uiso 1 1 calc R . . C27 C 0.8107(16) 0.7827(8) 0.3181(6) 0.0268(19) Uani 1 1 d . . . H10 H 0.9840 0.8121 0.3184 0.032 Uiso 1 1 calc R . . H11 H 0.7656 0.7157 0.2667 0.032 Uiso 1 1 calc R . . C28 C 0.9516(15) 1.0631(11) 0.7787(6) 0.034(2) Uani 1 1 d . . . C29 C 0.1271(15) 0.6420(9) 1.1293(5) 0.0282(18) Uani 1 1 d . . . H12 H 0.0387 0.7260 1.1391 0.034 Uiso 1 1 calc R . . C30 C 0.6115(17) 1.2000(10) 0.7829(6) 0.037(2) Uani 1 1 d . . . H13 H 0.4675 1.2244 0.7571 0.044 Uiso 1 1 calc R . . C31 C 1.0044(16) 0.9071(10) 0.6524(5) 0.031(2) Uani 1 1 d . . . H14 H 1.0931 0.8413 0.6233 0.038 Uiso 1 1 calc R . . C32 C 1.0840(16) 0.9676(12) 0.7336(6) 0.040(2) Uani 1 1 d . . . H15 H 1.2289 0.9449 0.7595 0.047 Uiso 1 1 calc R . . C33 C 0.1428(17) 1.0591(11) 0.1048(6) 0.035(2) Uani 1 1 d . . . H16 H 0.0231 0.9922 0.0760 0.042 Uiso 1 1 calc R . . C34 C 0.3546(17) 1.0880(12) 0.0666(6) 0.040(2) Uani 1 1 d . . . H17 H 0.3817 1.0448 0.0112 0.048 Uiso 1 1 calc R . . C35 C -0.0419(17) 0.5116(10) 1.1267(6) 0.037(2) Uani 1 1 d . . . H18 H 0.0443 0.4294 1.1160 0.056 Uiso 1 1 calc R . . H19 H -0.1647 0.5129 1.0800 0.056 Uiso 1 1 calc R . . H20 H -0.1169 0.5064 1.1825 0.056 Uiso 1 1 calc R . . C36 C 0.4603(17) 1.4452(11) 0.6008(6) 0.035(2) Uani 1 1 d . . . H21 H 0.5844 1.5108 0.6281 0.042 Uiso 1 1 calc R . . C37 C 0.2476(18) 1.4220(10) 0.6398(6) 0.036(2) Uani 1 1 d . . . H22 H 0.2244 1.4713 0.6937 0.043 Uiso 1 1 calc R . . C38 C 0.5292(15) 1.1838(11) 0.1123(6) 0.034(2) Uani 1 1 d . . . H23 H 0.6773 1.2066 0.0872 0.041 Uiso 1 1 calc R . . C39 C 0.4778(19) 0.7348(12) 1.0470(6) 0.048(3) Uani 1 1 d . . . H24 H 0.5430 0.7826 1.1002 0.058 Uiso 1 1 calc R . . C40 C 1.0311(19) 1.1269(14) 0.8623(7) 0.050(3) Uani 1 1 d . . . H25 H 1.1745 1.1044 0.8896 0.060 Uiso 1 1 calc R . . C41 C 0.516(2) 0.6884(11) 0.8934(7) 0.054(3) Uani 1 1 d . . . C42 C 0.696(2) 1.2590(13) 0.8644(7) 0.050(3) Uani 1 1 d . . . H26 H 0.6122 1.3269 0.8938 0.060 Uiso 1 1 calc R . . C43 C 0.609(2) 0.7526(15) 0.9733(7) 0.065(4) Uani 1 1 d . . . H27 H 0.7593 0.8079 0.9777 0.077 Uiso 1 1 calc R . . C44 C 0.900(2) 1.2210(15) 0.9036(7) 0.055(3) Uani 1 1 d . . . H28 H 0.9506 1.2606 0.9604 0.066 Uiso 1 1 calc R . . C45 C 0.651(3) 0.7041(18) 0.8136(9) 0.084(5) Uani 1 1 d . . . H29 H 0.6778 0.6109 0.7882 0.126 Uiso 1 1 calc R . . H30 H 0.8044 0.7605 0.8286 0.126 Uiso 1 1 calc R . . H31 H 0.5594 0.7513 0.7714 0.126 Uiso 1 1 calc R . . C46 C 0.307(4) 0.607(2) 0.8951(9) 0.126(10) Uani 1 1 d . . . H32 H 0.2456 0.5536 0.8430 0.151 Uiso 1 1 calc R . . C47 C 0.177(3) 0.595(2) 0.9681(8) 0.105(7) Uani 1 1 d . . . H33 H 0.0218 0.5448 0.9635 0.126 Uiso 1 1 calc R . . H34 H 0.990(15) 0.780(8) 0.492(5) 0.013(19) Uiso 1 1 d . . . H41 H 0.323(14) 0.705(10) 1.214(5) 0.00(2) 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 O1 0.013(3) 0.012(3) 0.037(3) 0.001(2) 0.001(2) -0.005(2) O2 0.020(3) 0.020(3) 0.022(3) -0.004(2) -0.007(2) -0.004(2) O3 0.025(3) 0.018(3) 0.020(3) 0.004(2) 0.000(2) -0.002(2) O4 0.028(3) 0.011(3) 0.033(3) -0.005(2) -0.003(2) -0.005(2) O5 0.046(4) 0.016(3) 0.027(3) 0.002(3) -0.002(3) -0.011(3) N11 0.022(4) 0.019(3) 0.024(4) -0.007(3) -0.003(3) 0.000(3) O6 0.021(3) 0.019(3) 0.036(3) 0.001(2) -0.008(2) 0.002(2) N8 0.019(3) 0.010(3) 0.030(4) 0.001(3) -0.001(3) -0.002(3) C48 0.012(4) 0.017(4) 0.022(4) 0.009(3) 0.000(3) -0.005(3) C10 0.013(4) 0.017(4) 0.032(5) 0.002(4) 0.005(3) -0.002(3) C11 0.025(4) 0.010(3) 0.019(4) 0.010(3) 0.008(3) -0.006(3) C12 0.029(5) 0.019(4) 0.027(5) -0.005(4) 0.000(4) -0.009(4) N10 0.021(3) 0.011(3) 0.021(3) 0.002(3) 0.000(3) -0.002(2) C14 0.027(5) 0.029(5) 0.030(5) 0.006(4) 0.002(4) 0.001(4) C15 0.017(4) 0.016(4) 0.017(4) -0.006(3) -0.001(3) -0.005(3) C16 0.020(4) 0.020(4) 0.019(4) -0.001(3) 0.001(3) -0.004(3) C17 0.011(4) 0.020(4) 0.023(4) -0.001(3) -0.001(3) 0.002(3) C18 0.020(4) 0.008(3) 0.029(4) 0.001(3) 0.000(3) -0.006(3) C19 0.028(5) 0.011(4) 0.028(5) 0.004(3) 0.003(3) 0.000(3) C20 0.010(3) 0.014(4) 0.028(4) 0.002(3) -0.002(3) 0.002(3) C21 0.029(5) 0.022(4) 0.020(4) 0.000(3) -0.006(3) -0.005(3) C22 0.022(4) 0.023(4) 0.032(5) 0.002(3) -0.002(3) -0.008(3) C23 0.039(5) 0.024(4) 0.039(5) 0.002(4) 0.001(4) -0.015(4) C24 0.022(4) 0.026(4) 0.010(3) -0.002(3) -0.003(3) -0.009(3) C25 0.036(5) 0.031(4) 0.013(4) -0.006(3) 0.004(3) -0.012(4) C26 0.040(5) 0.042(5) 0.021(5) 0.004(4) 0.011(4) 0.012(4) C27 0.028(4) 0.016(4) 0.037(5) 0.006(4) 0.003(4) 0.004(3) C28 0.030(5) 0.047(5) 0.021(4) -0.010(4) 0.001(3) -0.012(4) C29 0.031(4) 0.033(5) 0.018(4) -0.001(3) 0.000(3) -0.003(4) C30 0.039(5) 0.038(5) 0.030(5) -0.010(4) -0.002(4) 0.000(4) C31 0.035(5) 0.036(5) 0.021(4) -0.005(4) -0.001(4) 0.000(4) C32 0.026(5) 0.068(7) 0.023(5) 0.005(4) -0.008(4) 0.000(5) C33 0.036(5) 0.035(5) 0.030(5) -0.007(4) -0.011(4) 0.000(4) C34 0.035(5) 0.058(7) 0.026(5) -0.009(5) -0.004(4) 0.014(5) C35 0.040(5) 0.040(5) 0.027(5) -0.002(4) -0.004(4) -0.012(4) C36 0.040(6) 0.034(5) 0.029(5) -0.007(4) 0.007(4) -0.003(4) C37 0.055(6) 0.031(5) 0.020(4) -0.010(4) 0.000(4) 0.002(4) C38 0.014(4) 0.045(6) 0.044(6) 0.009(4) 0.003(4) 0.002(4) C39 0.059(7) 0.057(7) 0.020(5) -0.014(5) 0.010(4) -0.026(6) C40 0.037(5) 0.081(8) 0.028(5) -0.002(5) -0.002(4) -0.008(5) C41 0.085(8) 0.040(6) 0.032(5) -0.001(5) 0.025(5) -0.028(6) C42 0.055(7) 0.056(7) 0.034(6) -0.016(5) 0.009(5) -0.006(5) C43 0.072(8) 0.070(8) 0.040(7) -0.011(6) 0.017(6) -0.035(7) C44 0.050(7) 0.083(9) 0.025(5) -0.015(5) 0.008(5) -0.014(6) C45 0.108(11) 0.080(10) 0.054(8) -0.014(7) 0.037(7) -0.039(9) C46 0.147(16) 0.17(2) 0.033(7) -0.038(10) 0.022(8) -0.097(15) C47 0.111(12) 0.156(16) 0.021(6) -0.025(8) 0.016(6) -0.092(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C11 1.267(9) . ? O2 C11 1.257(9) . ? O3 C48 1.219(9) . ? O4 C10 1.277(10) . ? O5 C29 1.454(10) . ? O5 H41 0.68(9) . ? N11 C48 1.330(10) . ? N11 C15 1.474(9) . ? N11 H34 0.93(8) . ? O6 C10 1.219(9) . ? N8 C18 1.510(9) . ? N8 H35 1.0330 . ? N8 H36 1.0330 . ? N8 H37 1.0330 . ? C48 C24 1.510(10) . ? C10 C15 1.535(11) . ? C11 C27 1.518(11) . ? C12 C17 1.383(11) . ? C12 C36 1.399(13) . ? C12 H1 0.9500 . ? N10 C20 1.492(9) . ? N10 H38 1.0330 . ? N10 H39 1.0330 . ? N10 H40 1.0330 . ? C14 C38 1.379(14) . ? C14 C19 1.380(12) . ? C14 H2 0.9500 . ? C15 C27 1.538(11) . ? C15 H3 1.0000 . ? C16 C26 1.392(12) . ? C16 C17 1.393(11) . ? C16 H4 0.9500 . ? C17 C20 1.496(11) . ? C18 C19 1.524(12) . ? C18 C20 1.546(9) . ? C18 H5 1.0000 . ? C19 C21 1.396(11) . ? C20 H6 1.0000 . ? C21 C33 1.369(13) . ? C21 H7 0.9500 . ? C22 C24 1.367(12) . ? C22 C25 1.449(11) . ? C22 H8 0.9500 . ? C23 C39 1.315(13) . ? C23 C47 1.395(14) . ? C23 C29 1.532(13) . ? C24 C31 1.414(12) . ? C25 C28 1.406(13) . ? C25 C30 1.421(13) . ? C26 C37 1.368(14) . ? C26 H9 0.9500 . ? C27 H10 0.9900 . ? C27 H11 0.9900 . ? C28 C32 1.411(14) . ? C28 C40 1.421(13) . ? C29 C35 1.484(12) . ? C29 H12 1.0000 . ? C30 C42 1.386(13) . ? C30 H13 0.9500 . ? C31 C32 1.379(12) . ? C31 H14 0.9500 . ? C32 H15 0.9500 . ? C33 C34 1.371(15) . ? C33 H16 0.9500 . ? C34 C38 1.400(14) . ? C34 H17 0.9500 . ? C35 H18 0.9800 . ? C35 H19 0.9800 . ? C35 H20 0.9800 . ? C36 C37 1.375(14) . ? C36 H21 0.9500 . ? C37 H22 0.9500 . ? C38 H23 0.9500 . ? C39 C43 1.398(15) . ? C39 H24 0.9500 . ? C40 C44 1.373(17) . ? C40 H25 0.9500 . ? C41 C46 1.35(2) . ? C41 C43 1.393(15) . ? C41 C45 1.490(17) . ? C42 C44 1.372(17) . ? C42 H26 0.9500 . ? C43 H27 0.9500 . ? C44 H28 0.9500 . ? C45 H29 0.9800 . ? C45 H30 0.9800 . ? C45 H31 0.9800 . ? C46 C47 1.38(2) . ? C46 H32 0.9500 . ? C47 H33 0.9500 . ? 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 C29 O5 H41 100(7) . . ? C48 N11 C15 122.2(6) . . ? C48 N11 H34 133(5) . . ? C15 N11 H34 104(5) . . ? C18 N8 H35 109.5 . . ? C18 N8 H36 109.5 . . ? H35 N8 H36 109.5 . . ? C18 N8 H37 109.5 . . ? H35 N8 H37 109.5 . . ? H36 N8 H37 109.5 . . ? O3 C48 N11 124.1(7) . . ? O3 C48 C24 120.7(7) . . ? N11 C48 C24 115.2(6) . . ? O6 C10 O4 125.8(8) . . ? O6 C10 C15 118.2(7) . . ? O4 C10 C15 115.7(6) . . ? O2 C11 O1 124.3(7) . . ? O2 C11 C27 117.8(7) . . ? O1 C11 C27 117.9(7) . . ? C17 C12 C36 119.6(8) . . ? C17 C12 H1 120.2 . . ? C36 C12 H1 120.2 . . ? C20 N10 H38 109.5 . . ? C20 N10 H39 109.5 . . ? H38 N10 H39 109.5 . . ? C20 N10 H40 109.5 . . ? H38 N10 H40 109.5 . . ? H39 N10 H40 109.5 . . ? C38 C14 C19 120.4(8) . . ? C38 C14 H2 119.8 . . ? C19 C14 H2 119.8 . . ? N11 C15 C10 107.8(6) . . ? N11 C15 C27 111.8(6) . . ? C10 C15 C27 106.9(6) . . ? N11 C15 H3 110.1 . . ? C10 C15 H3 110.1 . . ? C27 C15 H3 110.1 . . ? C26 C16 C17 119.1(8) . . ? C26 C16 H4 120.4 . . ? C17 C16 H4 120.4 . . ? C12 C17 C16 119.8(7) . . ? C12 C17 C20 118.6(7) . . ? C16 C17 C20 121.6(7) . . ? N8 C18 C19 109.8(6) . . ? N8 C18 C20 106.5(5) . . ? C19 C18 C20 112.1(6) . . ? N8 C18 H5 109.5 . . ? C19 C18 H5 109.5 . . ? C20 C18 H5 109.5 . . ? C14 C19 C21 118.2(8) . . ? C14 C19 C18 122.8(7) . . ? C21 C19 C18 119.0(7) . . ? N10 C20 C17 112.4(7) . . ? N10 C20 C18 106.9(5) . . ? C17 C20 C18 112.1(6) . . ? N10 C20 H6 108.5 . . ? C17 C20 H6 108.5 . . ? C18 C20 H6 108.5 . . ? C33 C21 C19 120.7(9) . . ? C33 C21 H7 119.7 . . ? C19 C21 H7 119.7 . . ? C24 C22 C25 120.2(7) . . ? C24 C22 H8 119.9 . . ? C25 C22 H8 119.9 . . ? C39 C23 C47 115.4(10) . . ? C39 C23 C29 124.5(8) . . ? C47 C23 C29 119.9(9) . . ? C22 C24 C31 120.2(7) . . ? C22 C24 C48 116.7(6) . . ? C31 C24 C48 123.0(7) . . ? C28 C25 C30 119.9(7) . . ? C28 C25 C22 118.7(8) . . ? C30 C25 C22 121.3(8) . . ? C37 C26 C16 121.4(9) . . ? C37 C26 H9 119.3 . . ? C16 C26 H9 119.3 . . ? C11 C27 C15 110.5(6) . . ? C11 C27 H10 109.6 . . ? C15 C27 H10 109.6 . . ? C11 C27 H11 109.6 . . ? C15 C27 H11 109.6 . . ? H10 C27 H11 108.1 . . ? C25 C28 C32 119.7(7) . . ? C25 C28 C40 118.9(9) . . ? C32 C28 C40 121.3(8) . . ? O5 C29 C35 105.5(7) . . ? O5 C29 C23 107.9(7) . . ? C35 C29 C23 114.7(7) . . ? O5 C29 H12 109.5 . . ? C35 C29 H12 109.5 . . ? C23 C29 H12 109.5 . . ? C42 C30 C25 118.8(9) . . ? C42 C30 H13 120.6 . . ? C25 C30 H13 120.6 . . ? C32 C31 C24 120.6(8) . . ? C32 C31 H14 119.7 . . ? C24 C31 H14 119.7 . . ? C31 C32 C28 120.5(8) . . ? C31 C32 H15 119.7 . . ? C28 C32 H15 119.7 . . ? C21 C33 C34 121.9(9) . . ? C21 C33 H16 119.1 . . ? C34 C33 H16 119.1 . . ? C33 C34 C38 117.4(9) . . ? C33 C34 H17 121.3 . . ? C38 C34 H17 121.3 . . ? C29 C35 H18 109.5 . . ? C29 C35 H19 109.5 . . ? H18 C35 H19 109.5 . . ? C29 C35 H20 109.5 . . ? H18 C35 H20 109.5 . . ? H19 C35 H20 109.5 . . ? C37 C36 C12 120.6(9) . . ? C37 C36 H21 119.7 . . ? C12 C36 H21 119.7 . . ? C26 C37 C36 119.4(9) . . ? C26 C37 H22 120.3 . . ? C36 C37 H22 120.3 . . ? C14 C38 C34 121.4(9) . . ? C14 C38 H23 119.3 . . ? C34 C38 H23 119.3 . . ? C23 C39 C43 125.1(9) . . ? C23 C39 H24 117.4 . . ? C43 C39 H24 117.4 . . ? C44 C40 C28 119.7(10) . . ? C44 C40 H25 120.1 . . ? C28 C40 H25 120.1 . . ? C46 C41 C43 115.5(11) . . ? C46 C41 C45 123.6(11) . . ? C43 C41 C45 120.8(11) . . ? C44 C42 C30 121.2(11) . . ? C44 C42 H26 119.4 . . ? C30 C42 H26 119.4 . . ? C41 C43 C39 119.3(11) . . ? C41 C43 H27 120.3 . . ? C39 C43 H27 120.3 . . ? C42 C44 C40 121.3(10) . . ? C42 C44 H28 119.3 . . ? C40 C44 H28 119.3 . . ? C41 C45 H29 109.5 . . ? C41 C45 H30 109.5 . . ? H29 C45 H30 109.5 . . ? C41 C45 H31 109.5 . . ? H29 C45 H31 109.5 . . ? H30 C45 H31 109.5 . . ? C41 C46 C47 123.9(11) . . ? C41 C46 H32 118.1 . . ? C47 C46 H32 118.1 . . ? C46 C47 C23 120.3(12) . . ? C46 C47 H33 119.8 . . ? C23 C47 H33 119.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 N11 C48 O3 -11.3(12) . . . . ? C15 N11 C48 C24 170.1(7) . . . . ? C48 N11 C15 C10 -143.0(7) . . . . ? C48 N11 C15 C27 99.9(8) . . . . ? O6 C10 C15 N11 -23.6(10) . . . . ? O4 C10 C15 N11 162.2(7) . . . . ? O6 C10 C15 C27 96.7(8) . . . . ? O4 C10 C15 C27 -77.5(8) . . . . ? C36 C12 C17 C16 -2.1(13) . . . . ? C36 C12 C17 C20 176.2(8) . . . . ? C26 C16 C17 C12 1.2(12) . . . . ? C26 C16 C17 C20 -177.1(8) . . . . ? C38 C14 C19 C21 0.0(12) . . . . ? C38 C14 C19 C18 179.0(8) . . . . ? N8 C18 C19 C14 43.6(10) . . . . ? C20 C18 C19 C14 -74.5(9) . . . . ? N8 C18 C19 C21 -137.4(7) . . . . ? C20 C18 C19 C21 104.4(8) . . . . ? C12 C17 C20 N10 137.4(7) . . . . ? C16 C17 C20 N10 -44.2(9) . . . . ? C12 C17 C20 C18 -102.2(8) . . . . ? C16 C17 C20 C18 76.1(9) . . . . ? N8 C18 C20 N10 179.6(7) . . . . ? C19 C18 C20 N10 -60.4(7) . . . . ? N8 C18 C20 C17 56.0(7) . . . . ? C19 C18 C20 C17 176.0(7) . . . . ? C14 C19 C21 C33 2.4(12) . . . . ? C18 C19 C21 C33 -176.6(8) . . . . ? C25 C22 C24 C31 2.1(12) . . . . ? C25 C22 C24 C48 178.0(7) . . . . ? O3 C48 C24 C22 -8.9(11) . . . . ? N11 C48 C24 C22 169.8(7) . . . . ? O3 C48 C24 C31 166.9(8) . . . . ? N11 C48 C24 C31 -14.4(11) . . . . ? C24 C22 C25 C28 -3.9(12) . . . . ? C24 C22 C25 C30 179.7(8) . . . . ? C17 C16 C26 C37 0.4(13) . . . . ? O2 C11 C27 C15 -90.3(8) . . . . ? O1 C11 C27 C15 87.6(8) . . . . ? N11 C15 C27 C11 -64.0(8) . . . . ? C10 C15 C27 C11 178.2(7) . . . . ? C30 C25 C28 C32 -179.1(9) . . . . ? C22 C25 C28 C32 4.5(13) . . . . ? C30 C25 C28 C40 -2.5(14) . . . . ? C22 C25 C28 C40 -179.0(9) . . . . ? C39 C23 C29 O5 -39.4(13) . . . . ? C47 C23 C29 O5 146.0(13) . . . . ? C39 C23 C29 C35 -156.7(11) . . . . ? C47 C23 C29 C35 28.7(16) . . . . ? C28 C25 C30 C42 2.4(14) . . . . ? C22 C25 C30 C42 178.8(9) . . . . ? C22 C24 C31 C32 -0.8(14) . . . . ? C48 C24 C31 C32 -176.5(8) . . . . ? C24 C31 C32 C28 1.5(15) . . . . ? C25 C28 C32 C31 -3.3(15) . . . . ? C40 C28 C32 C31 -179.8(10) . . . . ? C19 C21 C33 C34 -3.5(15) . . . . ? C21 C33 C34 C38 1.9(15) . . . . ? C17 C12 C36 C37 1.4(15) . . . . ? C16 C26 C37 C36 -1.1(15) . . . . ? C12 C36 C37 C26 0.2(15) . . . . ? C19 C14 C38 C34 -1.5(14) . . . . ? C33 C34 C38 C14 0.5(15) . . . . ? C47 C23 C39 C43 -3(2) . . . . ? C29 C23 C39 C43 -178.2(12) . . . . ? C25 C28 C40 C44 2.5(16) . . . . ? C32 C28 C40 C44 178.9(11) . . . . ? C25 C30 C42 C44 -2.3(17) . . . . ? C46 C41 C43 C39 -3(2) . . . . ? C45 C41 C43 C39 -179.5(15) . . . . ? C23 C39 C43 C41 2(2) . . . . ? C30 C42 C44 C40 2(2) . . . . ? C28 C40 C44 C42 -2.3(19) . . . . ? C43 C41 C46 C47 6(3) . . . . ? C45 C41 C46 C47 -178(2) . . . . ? C41 C46 C47 C23 -8(4) . . . . ? C39 C23 C47 C46 6(3) . . . . ? C29 C23 C47 C46 -179.1(19) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.401 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.088 #============================================================================== # start Validation Reply Form _vrf_PLAT211_ ; PROBLRM: ADP of Atom C11 is N.P.D. or (nearly) 2D ... ? RESPONSE: Our calculations show that although the smallprincipal mean square displacements of the C atoms are very small. However using isotropic atomic displacement for all atom positions, yields a very similar model. ; # end Validation Reply Form #==============================================================================