data_cl21031s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H35 N3 O4' _chemical_formula_weight 513.62 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' 'y+1/2, x+1/2, -z+1/2' '-y, -x, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' '-y-1/2, -x-1/2, z-1/2' 'y, x, z-1/2' _cell_length_a 28.2016(11) _cell_length_b 28.2016(11) _cell_length_c 15.4533(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 12290.5(12) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.110 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4384 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40683 _diffrn_reflns_av_R_equivalents 0.0684 _diffrn_reflns_av_sigmaI/netI 0.0637 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 24.99 _reflns_number_total 5300 _reflns_number_gt 2642 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1376P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5300 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1441 _refine_ls_R_factor_gt 0.0704 _refine_ls_wR_factor_ref 0.2516 _refine_ls_wR_factor_gt 0.2291 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 N1 N 0.54350(10) 0.10906(11) 0.9865(2) 0.0496(8) Uani 1 1 d . . . H1 H 0.5383 0.1296 1.0265 0.059 Uiso 1 1 calc R . . N2 N 0.53180(10) 0.05621(11) 0.8894(2) 0.0491(8) Uani 1 1 d . . . N3 N 0.31054(11) 0.10103(11) 0.9739(2) 0.0543(9) Uani 1 1 d . . . O1 O 0.23961(9) 0.12654(9) 1.11321(19) 0.0598(8) Uani 1 1 d . . . O2 O 0.19614(11) 0.05161(11) 1.2088(2) 0.0756(9) Uani 1 1 d . . . O3 O 0.17834(10) -0.03578(10) 1.1159(2) 0.0698(8) Uani 1 1 d . . . O4 O 0.23831(10) -0.00723(10) 0.97630(19) 0.0680(9) Uani 1 1 d . . . C1 C 0.58831(13) 0.09769(13) 0.9543(3) 0.0506(10) Uani 1 1 d . . . C2 C 0.58142(13) 0.06460(14) 0.8934(2) 0.0483(10) Uani 1 1 d . . . C3 C 0.50986(13) 0.08402(13) 0.9472(2) 0.0456(9) Uani 1 1 d . . . C11 C 0.63093(13) 0.11885(14) 0.9947(3) 0.0517(10) Uani 1 1 d . . . C12 C 0.63894(16) 0.11129(18) 1.0823(3) 0.0758(14) Uani 1 1 d . . . H12 H 0.6187 0.0919 1.1140 0.091 Uiso 1 1 calc R . . C13 C 0.67761(19) 0.1330(2) 1.1225(4) 0.0939(17) Uani 1 1 d . . . H13 H 0.6829 0.1285 1.1813 0.113 Uiso 1 1 calc R . . C14 C 0.70761(19) 0.1607(2) 1.0752(5) 0.0961(18) Uani 1 1 d . . . H14 H 0.7337 0.1744 1.1020 0.115 Uiso 1 1 calc R . . C15 C 0.70003(17) 0.16842(16) 0.9903(4) 0.0810(15) Uani 1 1 d . . . H15 H 0.7209 0.1874 0.9590 0.097 Uiso 1 1 calc R . . C16 C 0.66059(14) 0.14786(15) 0.9490(3) 0.0675(12) Uani 1 1 d . . . H16 H 0.6547 0.1540 0.8909 0.081 Uiso 1 1 calc R . . C21 C 0.61361(13) 0.03721(15) 0.8359(2) 0.0515(10) Uani 1 1 d . . . C22 C 0.64820(15) 0.06008(18) 0.7881(3) 0.0701(13) Uani 1 1 d . . . H22 H 0.6523 0.0926 0.7939 0.084 Uiso 1 1 calc R . . C23 C 0.67686(17) 0.0349(3) 0.7315(3) 0.0877(16) Uani 1 1 d . . . H23 H 0.6994 0.0504 0.6978 0.105 Uiso 1 1 calc R . . C24 C 0.67155(19) -0.0128(2) 0.7260(4) 0.0878(17) Uani 1 1 d . . . H24 H 0.6915 -0.0298 0.6895 0.105 Uiso 1 1 calc R . . C25 C 0.6384(2) -0.0364(2) 0.7715(4) 0.0877(16) Uani 1 1 d . . . H25 H 0.6352 -0.0690 0.7657 0.105 Uiso 1 1 calc R . . C26 C 0.60872(16) -0.01109(18) 0.8277(3) 0.0691(13) Uani 1 1 d . . . H26 H 0.5857 -0.0270 0.8596 0.083 Uiso 1 1 calc R . . C31 C 0.45893(12) 0.08741(14) 0.9599(2) 0.0456(9) Uani 1 1 d . . . C32 C 0.43781(12) 0.12929(14) 0.9891(3) 0.0488(10) Uani 1 1 d . . . H32 H 0.4569 0.1547 1.0049 0.059 Uiso 1 1 calc R . . C33 C 0.38990(13) 0.13352(13) 0.9948(2) 0.0494(10) Uani 1 1 d . . . H33 H 0.3770 0.1621 1.0135 0.059 Uiso 1 1 calc R . . C34 C 0.35937(12) 0.09602(13) 0.9734(2) 0.0425(9) Uani 1 1 d . . . C35 C 0.38063(13) 0.05349(14) 0.9475(3) 0.0510(10) Uani 1 1 d . . . H35 H 0.3617 0.0275 0.9342 0.061 Uiso 1 1 calc R . . C36 C 0.42909(13) 0.04975(14) 0.9413(2) 0.0520(10) Uani 1 1 d . . . H36 H 0.4423 0.0210 0.9241 0.062 Uiso 1 1 calc R . . C37 C 0.28889(14) 0.14737(15) 0.9942(3) 0.0655(12) Uani 1 1 d . . . H37A H 0.2592 0.1501 0.9628 0.079 Uiso 1 1 calc R . . H37B H 0.3098 0.1723 0.9738 0.079 Uiso 1 1 calc R . . C38 C 0.27949(14) 0.15483(15) 1.0882(3) 0.0707(14) Uani 1 1 d . . . H38A H 0.3071 0.1458 1.1217 0.085 Uiso 1 1 calc R . . H38B H 0.2729 0.1881 1.0991 0.085 Uiso 1 1 calc R . . C39 C 0.23045(18) 0.12685(16) 1.2023(3) 0.0745(13) Uani 1 1 d . . . H39A H 0.2271 0.1593 1.2221 0.089 Uiso 1 1 calc R . . H39B H 0.2569 0.1127 1.2328 0.089 Uiso 1 1 calc R . . C40 C 0.18735(18) 0.10067(17) 1.2218(3) 0.0777(14) Uani 1 1 d . . . H40A H 0.1779 0.1063 1.2812 0.093 Uiso 1 1 calc R . . H40B H 0.1619 0.1111 1.1842 0.093 Uiso 1 1 calc R . . C41 C 0.1545(2) 0.02390(19) 1.2166(3) 0.0843(15) Uani 1 1 d . . . H41A H 0.1313 0.0341 1.1741 0.101 Uiso 1 1 calc R . . H41B H 0.1408 0.0282 1.2737 0.101 Uiso 1 1 calc R . . C42 C 0.1661(2) -0.02743(19) 1.2028(4) 0.0947(17) Uani 1 1 d . . . H42A H 0.1924 -0.0364 1.2399 0.114 Uiso 1 1 calc R . . H42B H 0.1390 -0.0468 1.2183 0.114 Uiso 1 1 calc R . . C43 C 0.22503(18) -0.05389(19) 1.1045(4) 0.0945(18) Uani 1 1 d . . . H43A H 0.2262 -0.0864 1.1248 0.113 Uiso 1 1 calc R . . H43B H 0.2470 -0.0354 1.1391 0.113 Uiso 1 1 calc R . . C44 C 0.23945(18) -0.05228(17) 1.0153(4) 0.0890(17) Uani 1 1 d . . . H44A H 0.2715 -0.0645 1.0112 0.107 Uiso 1 1 calc R . . H44B H 0.2191 -0.0733 0.9824 0.107 Uiso 1 1 calc R . . C45 C 0.27037(14) 0.02610(14) 1.0141(3) 0.0598(11) Uani 1 1 d . . . H45A H 0.2997 0.0106 1.0303 0.072 Uiso 1 1 calc R . . H45B H 0.2565 0.0402 1.0654 0.072 Uiso 1 1 calc R . . C46 C 0.27936(13) 0.06294(14) 0.9473(3) 0.0535(11) Uani 1 1 d . . . H46A H 0.2930 0.0477 0.8968 0.064 Uiso 1 1 calc R . . H46B H 0.2492 0.0765 0.9301 0.064 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0350(18) 0.060(2) 0.0535(19) -0.0117(16) 0.0034(15) -0.0008(16) N2 0.0344(17) 0.059(2) 0.054(2) -0.0028(16) 0.0056(15) 0.0004(15) N3 0.0397(19) 0.057(2) 0.066(2) 0.0031(17) 0.0023(16) -0.0003(16) O1 0.0524(17) 0.0573(17) 0.070(2) -0.0108(14) -0.0046(14) -0.0059(14) O2 0.080(2) 0.071(2) 0.076(2) -0.0005(17) 0.0020(17) -0.0020(18) O3 0.070(2) 0.0679(19) 0.071(2) 0.0035(16) -0.0100(16) 0.0014(16) O4 0.0620(19) 0.0588(18) 0.083(2) -0.0065(16) 0.0040(16) -0.0109(15) C1 0.039(2) 0.048(2) 0.064(3) -0.001(2) -0.005(2) -0.0004(18) C2 0.040(2) 0.060(2) 0.044(2) 0.002(2) 0.0014(19) 0.0049(19) C3 0.040(2) 0.054(2) 0.043(2) -0.0015(19) 0.0022(18) -0.0035(19) C11 0.037(2) 0.052(2) 0.066(3) -0.003(2) 0.000(2) 0.0042(19) C12 0.054(3) 0.099(4) 0.075(3) -0.001(3) -0.009(2) -0.016(3) C13 0.076(4) 0.104(4) 0.101(4) -0.009(4) -0.027(3) -0.001(3) C14 0.065(3) 0.080(4) 0.143(6) -0.029(4) -0.020(4) -0.010(3) C15 0.057(3) 0.057(3) 0.129(5) 0.006(3) -0.005(3) -0.007(2) C16 0.051(3) 0.062(3) 0.089(3) 0.010(2) -0.001(2) 0.000(2) C21 0.034(2) 0.074(3) 0.046(2) 0.000(2) -0.0006(18) 0.007(2) C22 0.053(3) 0.091(3) 0.067(3) -0.001(3) 0.004(2) 0.011(2) C23 0.056(3) 0.142(5) 0.066(3) -0.003(3) 0.010(2) 0.011(3) C24 0.066(4) 0.110(5) 0.087(4) -0.028(4) 0.002(3) 0.020(3) C25 0.082(4) 0.094(4) 0.088(4) -0.024(3) -0.006(3) 0.015(3) C26 0.062(3) 0.080(3) 0.065(3) -0.004(3) 0.011(2) 0.007(3) C31 0.039(2) 0.055(2) 0.044(2) -0.0072(19) 0.0004(17) -0.0031(19) C32 0.038(2) 0.051(2) 0.057(3) -0.0037(19) 0.0000(18) -0.0087(18) C33 0.043(2) 0.049(2) 0.056(2) -0.0030(19) 0.0056(19) 0.0028(19) C34 0.037(2) 0.047(2) 0.044(2) 0.0014(17) 0.0020(16) -0.0051(18) C35 0.038(2) 0.059(3) 0.056(3) -0.009(2) 0.0016(19) -0.0132(19) C36 0.050(2) 0.055(2) 0.051(2) -0.013(2) 0.0081(19) 0.004(2) C37 0.042(2) 0.064(3) 0.090(4) 0.013(3) -0.004(2) 0.000(2) C38 0.043(2) 0.055(3) 0.114(4) -0.016(3) -0.003(3) 0.003(2) C39 0.092(4) 0.065(3) 0.066(3) -0.015(2) -0.016(3) 0.010(3) C40 0.092(4) 0.081(4) 0.060(3) -0.001(3) 0.003(3) 0.016(3) C41 0.104(4) 0.100(4) 0.048(3) -0.002(3) 0.008(3) -0.015(3) C42 0.118(4) 0.092(4) 0.075(4) 0.026(3) -0.014(3) -0.020(3) C43 0.074(4) 0.084(4) 0.125(5) 0.044(4) -0.016(3) 0.016(3) C44 0.066(3) 0.061(3) 0.141(6) -0.002(3) 0.010(3) 0.009(3) C45 0.053(2) 0.060(3) 0.067(3) -0.002(2) -0.002(2) -0.007(2) C46 0.039(2) 0.062(3) 0.060(3) 0.006(2) -0.003(2) -0.0029(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C3 1.329(4) . ? N1 C1 1.396(4) . ? N2 C3 1.340(4) . ? N2 C2 1.420(4) . ? N3 C34 1.384(4) . ? N3 C46 1.448(5) . ? N3 C37 1.476(5) . ? O1 C39 1.401(5) . ? O1 C38 1.432(5) . ? O2 C41 1.417(6) . ? O2 C40 1.420(5) . ? O3 C42 1.406(6) . ? O3 C43 1.423(6) . ? O4 C44 1.407(6) . ? O4 C45 1.429(5) . ? C1 C2 1.339(5) . ? C1 C11 1.481(5) . ? C2 C21 1.487(5) . ? C3 C31 1.453(5) . ? C11 C16 1.367(6) . ? C11 C12 1.389(6) . ? C12 C13 1.395(7) . ? C13 C14 1.364(8) . ? C14 C15 1.346(7) . ? C15 C16 1.408(6) . ? C21 C26 1.375(6) . ? C21 C22 1.383(6) . ? C22 C23 1.387(7) . ? C23 C24 1.355(7) . ? C24 C25 1.347(7) . ? C25 C26 1.401(6) . ? C31 C36 1.385(5) . ? C31 C32 1.398(5) . ? C32 C33 1.359(5) . ? C33 C34 1.403(5) . ? C34 C35 1.399(5) . ? C35 C36 1.374(5) . ? C37 C38 1.492(6) . ? C39 C40 1.454(6) . ? C41 C42 1.500(7) . ? C43 C44 1.437(8) . ? C45 C46 1.486(5) . ? 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 C3 N1 C1 111.2(3) . . ? C3 N2 C2 109.2(3) . . ? C34 N3 C46 121.8(3) . . ? C34 N3 C37 120.2(3) . . ? C46 N3 C37 117.8(3) . . ? C39 O1 C38 114.0(3) . . ? C41 O2 C40 112.4(4) . . ? C42 O3 C43 113.9(4) . . ? C44 O4 C45 113.9(4) . . ? C2 C1 N1 106.2(3) . . ? C2 C1 C11 134.1(4) . . ? N1 C1 C11 119.5(3) . . ? C1 C2 N2 106.8(3) . . ? C1 C2 C21 133.9(3) . . ? N2 C2 C21 119.3(3) . . ? N1 C3 N2 106.6(3) . . ? N1 C3 C31 127.5(3) . . ? N2 C3 C31 125.8(3) . . ? C16 C11 C12 119.8(4) . . ? C16 C11 C1 121.3(4) . . ? C12 C11 C1 118.8(4) . . ? C11 C12 C13 119.5(5) . . ? C14 C13 C12 119.8(6) . . ? C15 C14 C13 121.1(5) . . ? C14 C15 C16 120.0(5) . . ? C11 C16 C15 119.7(5) . . ? C26 C21 C22 118.9(4) . . ? C26 C21 C2 120.5(4) . . ? C22 C21 C2 120.5(4) . . ? C21 C22 C23 120.6(5) . . ? C24 C23 C22 118.9(5) . . ? C25 C24 C23 122.3(5) . . ? C24 C25 C26 119.2(5) . . ? C21 C26 C25 120.1(5) . . ? C36 C31 C32 117.1(3) . . ? C36 C31 C3 121.5(3) . . ? C32 C31 C3 121.4(3) . . ? C33 C32 C31 121.2(3) . . ? C32 C33 C34 121.9(4) . . ? N3 C34 C35 121.0(3) . . ? N3 C34 C33 122.1(3) . . ? C35 C34 C33 116.8(3) . . ? C36 C35 C34 120.8(3) . . ? C35 C36 C31 122.1(4) . . ? N3 C37 C38 113.9(4) . . ? O1 C38 C37 108.9(4) . . ? O1 C39 C40 110.7(4) . . ? O2 C40 C39 108.6(4) . . ? O2 C41 C42 109.8(4) . . ? O3 C42 C41 110.5(4) . . ? O3 C43 C44 111.7(4) . . ? O4 C44 C43 115.7(4) . . ? O4 C45 C46 106.5(3) . . ? N3 C46 C45 115.2(3) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.341 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.047