# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ts #TrackingRef 'TS 507.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H30 N2 O5' _chemical_formula_sum 'C26 H30 N2 O5' _chemical_formula_weight 450.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5277(8) _cell_length_b 11.7075(12) _cell_length_c 24.388(2) _cell_angle_alpha 87.450(4) _cell_angle_beta 88.887(4) _cell_angle_gamma 81.918(4) _cell_volume 2408.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9445 _exptl_absorpt_correction_T_max 0.9696 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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_reflns_number 28168 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0400 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 0.84 _diffrn_reflns_theta_max 23.95 _reflns_number_total 7458 _reflns_number_gt 4686 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0800P)^2^+0.7000P] 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 7458 _refine_ls_number_parameters 605 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1751 _refine_ls_wR_factor_gt 0.1484 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.0994(4) 0.8113(3) 0.52856(13) 0.0707(9) Uani 1 1 d . . . H1A H -0.1882 0.8466 0.5065 0.085 Uiso 1 1 calc R . . H1B H -0.1159 0.8369 0.5658 0.085 Uiso 1 1 calc R . . N1 N 0.0488(3) 0.84345(18) 0.50574(8) 0.0519(6) Uani 1 1 d . . . O1 O 0.2864(3) 1.0411(2) 0.71797(9) 0.1012(8) Uani 1 1 d . . . C2 C -0.0855(6) 0.6853(4) 0.5280(3) 0.129(2) Uani 1 1 d . . . H2 H -0.1484 0.6399 0.5484 0.155 Uiso 1 1 calc R . . H2A H -0.172(9) 0.678(6) 0.502(3) 0.25(4) Uiso 1 1 d . . . N2 N 0.4526(3) 0.8600(2) 0.54966(9) 0.0594(6) Uani 1 1 d . . . O2 O 0.0742(3) 0.7148(2) 0.38040(9) 0.1000(8) Uani 1 1 d . . . C3 C 0.0432(4) 0.6420(3) 0.49039(14) 0.0733(9) Uani 1 1 d . . . H3A H 0.0011 0.6131 0.4579 0.088 Uiso 1 1 calc R . . H3B H 0.1145 0.5801 0.5082 0.088 Uiso 1 1 calc R . . N3 N 0.1158(3) 0.3370(2) 0.00615(9) 0.0638(7) Uani 1 1 d . . . O3 O 0.1786(2) 0.87249(17) 0.39975(7) 0.0665(5) Uani 1 1 d . . . C4 C 0.1306(3) 0.7458(2) 0.47499(11) 0.0535(7) Uani 1 1 d . . . N4 N 0.5271(3) 0.3270(2) 0.04771(9) 0.0595(6) Uani 1 1 d . . . O4 O 0.4796(3) 0.95607(19) 0.55944(9) 0.0839(7) Uani 1 1 d . . . C5 C 0.3068(3) 0.7331(2) 0.49317(10) 0.0489(6) Uani 1 1 d . . . H5 H 0.3168 0.6809 0.5258 0.059 Uiso 1 1 calc R . . O5 O 0.5252(3) 0.7716(2) 0.56940(9) 0.0828(7) Uani 1 1 d . . . C6 C 0.3164(3) 0.8534(2) 0.51220(10) 0.0474(6) Uani 1 1 d . . . H6 H 0.3245 0.9056 0.4801 0.057 Uiso 1 1 calc R . . O6 O 0.1322(3) 0.5842(2) 0.21181(8) 0.0914(8) Uani 1 1 d . . . C7 C 0.1582(3) 0.8895(2) 0.54216(10) 0.0516(7) Uani 1 1 d . . . H7 H 0.1351 0.9739 0.5406 0.062 Uiso 1 1 calc R . . O7 O 0.5817(3) 0.4152(2) 0.05537(9) 0.0893(7) Uani 1 1 d . . . C8 C 0.1601(3) 0.8470(2) 0.60137(11) 0.0581(7) Uani 1 1 d . . . H8 H 0.1601 0.7685 0.6090 0.070 Uiso 1 1 calc R . . O8 O 0.5763(3) 0.2349(2) 0.07051(9) 0.0786(6) Uani 1 1 d . . . C9 C 0.1618(3) 0.9149(2) 0.64281(11) 0.0593(7) Uani 1 1 d . . . H9 H 0.1595 0.9933 0.6343 0.071 Uiso 1 1 calc R . . O9 O 0.1199(3) 0.2366(2) -0.12434(10) 0.1030(8) Uani 1 1 d . . . C10 C 0.1670(4) 0.8785(3) 0.70138(11) 0.0653(8) Uani 1 1 d . . . O10 O 0.2383(3) 0.3820(2) -0.09802(9) 0.0844(7) Uani 1 1 d . . . C11 C 0.1061(4) 0.7801(3) 0.72063(13) 0.0770(9) Uani 1 1 d . . . H11 H 0.0583 0.7374 0.6962 0.092 Uiso 1 1 calc R . . C12 C 0.1151(5) 0.7444(4) 0.77536(15) 0.0957(12) Uani 1 1 d . . . H12 H 0.0727 0.6788 0.7877 0.115 Uiso 1 1 calc R . . C13 C 0.1867(5) 0.8063(5) 0.81111(15) 0.1036(14) Uani 1 1 d . . . H13 H 0.1966 0.7806 0.8477 0.124 Uiso 1 1 calc R . . C14 C 0.2444(4) 0.9059(4) 0.79410(13) 0.0915(12) Uani 1 1 d . . . H14 H 0.2908 0.9484 0.8190 0.110 Uiso 1 1 calc R . . C15 C 0.2325(4) 0.9424(3) 0.73911(12) 0.0745(9) Uani 1 1 d . . . C16 C 0.3489(6) 1.1142(4) 0.75415(18) 0.1353(18) Uani 1 1 d . . . H16A H 0.2711 1.1378 0.7819 0.203 Uiso 1 1 calc R . . H16B H 0.3757 1.1811 0.7339 0.203 Uiso 1 1 calc R . . H16C H 0.4421 1.0732 0.7711 0.203 Uiso 1 1 calc R . . C17 C 0.4296(3) 0.6834(2) 0.45173(11) 0.0515(7) Uani 1 1 d . . . C18 C 0.4391(4) 0.5692(2) 0.43855(13) 0.0660(8) Uani 1 1 d . . . H18 H 0.3701 0.5233 0.4555 0.079 Uiso 1 1 calc R . . C19 C 0.5493(4) 0.5216(3) 0.40067(13) 0.0736(9) Uani 1 1 d . . . H19 H 0.5510 0.4449 0.3919 0.088 Uiso 1 1 calc R . . C20 C 0.6565(4) 0.5852(3) 0.37564(13) 0.0722(9) Uani 1 1 d . . . C21 C 0.6479(4) 0.6980(3) 0.38886(14) 0.0797(10) Uani 1 1 d . . . H21 H 0.7186 0.7430 0.3723 0.096 Uiso 1 1 calc R . . C22 C 0.5370(4) 0.7473(3) 0.42607(12) 0.0677(8) Uani 1 1 d . . . H22 H 0.5345 0.8245 0.4340 0.081 Uiso 1 1 calc R . . C23 C 0.7794(5) 0.5308(4) 0.33546(17) 0.1126(14) Uani 1 1 d . . . H23A H 0.8019 0.5879 0.3081 0.169 Uiso 1 1 calc R . . H23B H 0.7397 0.4689 0.3182 0.169 Uiso 1 1 calc R . . H23C H 0.8747 0.5012 0.3547 0.169 Uiso 1 1 calc R . . C24 C 0.1216(3) 0.7744(3) 0.41347(12) 0.0616(8) Uani 1 1 d . . . C25 C 0.1984(4) 0.8976(3) 0.34132(12) 0.0785(10) Uani 1 1 d . . . H25A H 0.2663 0.8345 0.3248 0.094 Uiso 1 1 calc R . . H25B H 0.0965 0.9072 0.3234 0.094 Uiso 1 1 calc R . . C26 C 0.2692(5) 1.0032(4) 0.33445(14) 0.1047(13) Uani 1 1 d . . . H26A H 0.2021 1.0649 0.3514 0.157 Uiso 1 1 calc R . . H26B H 0.2812 1.0221 0.2960 0.157 Uiso 1 1 calc R . . H26C H 0.3712 0.9923 0.3514 0.157 Uiso 1 1 calc R . . C27 C -0.0279(4) 0.3036(3) 0.03224(15) 0.0896(11) Uani 1 1 d . . . H27A H -0.0292 0.3171 0.0712 0.107 Uiso 1 1 calc R . . H27B H -0.1213 0.3480 0.0159 0.107 Uiso 1 1 calc R . . C28 C -0.0252(7) 0.1831(4) 0.0235(2) 0.172(3) Uani 1 1 d . . . H28A H -0.0023 0.1393 0.0578 0.207 Uiso 1 1 calc R . . H28B H -0.1288 0.1697 0.0117 0.207 Uiso 1 1 calc R . . C29 C 0.0908(4) 0.1433(3) -0.01680(14) 0.0754(9) Uani 1 1 d . . . H29A H 0.0403 0.1243 -0.0498 0.090 Uiso 1 1 calc R . . H29B H 0.1587 0.0752 -0.0029 0.090 Uiso 1 1 calc R . . C30 C 0.1873(3) 0.2435(2) -0.02887(11) 0.0544(7) Uani 1 1 d . . . C31 C 0.3645(3) 0.2194(2) -0.01150(10) 0.0478(6) Uani 1 1 d . . . H31 H 0.3706 0.1643 0.0201 0.057 Uiso 1 1 calc R . . C32 C 0.3894(3) 0.3350(2) 0.00979(10) 0.0509(7) Uani 1 1 d . . . H32 H 0.4064 0.3877 -0.0214 0.061 Uiso 1 1 calc R . . C33 C 0.2334(3) 0.3814(2) 0.03963(11) 0.0564(7) Uani 1 1 d . . . H33 H 0.2175 0.4659 0.0354 0.068 Uiso 1 1 calc R . . C34 C 0.2372(4) 0.3487(2) 0.09978(11) 0.0619(8) Uani 1 1 d . . . H34 H 0.2387 0.2713 0.1106 0.074 Uiso 1 1 calc R . . C35 C 0.2385(3) 0.4246(2) 0.13804(11) 0.0613(8) Uani 1 1 d . . . H35 H 0.2215 0.5020 0.1264 0.074 Uiso 1 1 calc R . . C36 C 0.2638(4) 0.4000(3) 0.19712(11) 0.0635(8) Uani 1 1 d . . . C37 C 0.2114(4) 0.4835(3) 0.23442(12) 0.0687(8) Uani 1 1 d . . . C38 C 0.2360(5) 0.4630(4) 0.28991(13) 0.0892(11) Uani 1 1 d . . . H38 H 0.1989 0.5193 0.3146 0.107 Uiso 1 1 calc R . . C39 C 0.3153(5) 0.3593(4) 0.30846(16) 0.1034(13) Uani 1 1 d . . . H39 H 0.3298 0.3449 0.3460 0.124 Uiso 1 1 calc R . . C40 C 0.3742(5) 0.2758(4) 0.27253(18) 0.1044(13) Uani 1 1 d . . . H40 H 0.4302 0.2062 0.2854 0.125 Uiso 1 1 calc R . . C41 C 0.3485(4) 0.2971(3) 0.21717(14) 0.0841(10) Uani 1 1 d . . . H41 H 0.3889 0.2413 0.1927 0.101 Uiso 1 1 calc R . . C42 C 0.1040(6) 0.6821(3) 0.24374(14) 0.1089(14) Uani 1 1 d . . . H42A H 0.0387 0.6663 0.2749 0.163 Uiso 1 1 calc R . . H42B H 0.0511 0.7460 0.2220 0.163 Uiso 1 1 calc R . . H42C H 0.2030 0.7010 0.2561 0.163 Uiso 1 1 calc R . . C43 C 0.4824(3) 0.1685(2) -0.05391(10) 0.0480(6) Uani 1 1 d . . . C44 C 0.4779(4) 0.0589(2) -0.07149(11) 0.0613(8) Uani 1 1 d . . . H44 H 0.4005 0.0167 -0.0574 0.074 Uiso 1 1 calc R . . C45 C 0.5862(4) 0.0102(3) -0.10968(12) 0.0689(9) Uani 1 1 d . . . H45 H 0.5791 -0.0637 -0.1210 0.083 Uiso 1 1 calc R . . C46 C 0.7041(4) 0.0680(3) -0.13141(11) 0.0667(8) Uani 1 1 d . . . C47 C 0.7089(4) 0.1773(3) -0.11430(13) 0.0803(10) Uani 1 1 d . . . H47 H 0.7867 0.2191 -0.1285 0.096 Uiso 1 1 calc R . . C48 C 0.6004(4) 0.2270(3) -0.07624(12) 0.0720(9) Uani 1 1 d . . . H48 H 0.6070 0.3013 -0.0654 0.086 Uiso 1 1 calc R . . C49 C 0.8257(5) 0.0133(3) -0.17215(15) 0.1037(13) Uani 1 1 d . . . H49A H 0.8183 0.0584 -0.2061 0.156 Uiso 1 1 calc R . . H49B H 0.8058 -0.0636 -0.1786 0.156 Uiso 1 1 calc R . . H49C H 0.9299 0.0105 -0.1575 0.156 Uiso 1 1 calc R . . C50 C 0.1754(4) 0.2853(3) -0.08888(12) 0.0645(8) Uani 1 1 d . . . C51 C 0.2330(6) 0.4359(4) -0.15288(16) 0.1194(16) Uani 1 1 d . . . H51A H 0.1695 0.3957 -0.1760 0.143 Uiso 1 1 calc R . . H51B H 0.1823 0.5152 -0.1511 0.143 Uiso 1 1 calc R . . C52 C 0.3828(6) 0.4347(5) -0.17637(18) 0.150(2) Uani 1 1 d . . . H52A H 0.4537 0.4562 -0.1498 0.225 Uiso 1 1 calc R . . H52B H 0.3773 0.4885 -0.2074 0.225 Uiso 1 1 calc R . . H52C H 0.4208 0.3585 -0.1882 0.225 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 C1 0.065(2) 0.076(2) 0.073(2) -0.0147(16) 0.0100(16) -0.0174(16) N1 0.0538(14) 0.0530(13) 0.0506(13) -0.0089(10) 0.0035(11) -0.0114(11) O1 0.130(2) 0.118(2) 0.0635(14) -0.0270(14) -0.0066(14) -0.0381(17) C2 0.111(4) 0.073(3) 0.208(6) -0.021(3) 0.078(4) -0.037(3) N2 0.0707(17) 0.0658(16) 0.0465(13) -0.0012(12) -0.0011(12) -0.0262(14) O2 0.115(2) 0.125(2) 0.0729(15) -0.0387(14) -0.0059(14) -0.0504(16) C3 0.070(2) 0.0606(18) 0.096(2) -0.0150(17) 0.0104(18) -0.0274(16) N3 0.0597(16) 0.0671(15) 0.0647(15) -0.0163(12) 0.0082(12) -0.0061(12) O3 0.0849(15) 0.0730(13) 0.0431(11) -0.0051(9) -0.0041(10) -0.0152(11) C4 0.0590(18) 0.0442(15) 0.0595(17) -0.0109(12) 0.0044(14) -0.0129(13) N4 0.0723(17) 0.0613(16) 0.0471(13) -0.0047(12) 0.0026(12) -0.0169(14) O4 0.1080(19) 0.0786(15) 0.0765(14) -0.0075(12) -0.0155(13) -0.0498(14) C5 0.0578(18) 0.0395(14) 0.0504(15) 0.0014(11) 0.0001(13) -0.0116(12) O5 0.0820(17) 0.0838(16) 0.0819(16) 0.0117(13) -0.0255(13) -0.0101(13) C6 0.0592(17) 0.0442(14) 0.0405(14) 0.0019(11) -0.0041(12) -0.0140(12) O6 0.121(2) 0.0869(16) 0.0618(13) -0.0313(12) -0.0187(13) 0.0128(14) C7 0.0666(19) 0.0443(14) 0.0446(15) -0.0035(12) -0.0003(13) -0.0103(13) O7 0.1096(19) 0.0767(15) 0.0926(16) -0.0064(12) -0.0222(14) -0.0471(14) C8 0.070(2) 0.0525(16) 0.0521(16) 0.0002(13) 0.0024(14) -0.0089(14) O8 0.0886(17) 0.0731(15) 0.0734(14) 0.0052(12) -0.0211(12) -0.0090(12) C9 0.068(2) 0.0598(17) 0.0481(16) -0.0047(14) 0.0005(14) -0.0029(14) O9 0.120(2) 0.123(2) 0.0748(16) -0.0138(14) -0.0274(15) -0.0403(17) C10 0.063(2) 0.082(2) 0.0461(17) -0.0087(16) 0.0024(14) 0.0078(16) O10 0.0970(18) 0.0965(16) 0.0652(14) 0.0194(12) -0.0186(12) -0.0376(14) C11 0.085(2) 0.085(2) 0.057(2) 0.0044(17) 0.0065(17) 0.0006(19) C12 0.096(3) 0.117(3) 0.066(2) 0.023(2) 0.010(2) 0.005(2) C13 0.088(3) 0.157(4) 0.053(2) 0.015(3) 0.008(2) 0.018(3) C14 0.081(3) 0.143(4) 0.046(2) -0.015(2) -0.0003(17) 0.003(2) C15 0.073(2) 0.095(2) 0.0535(19) -0.0103(18) 0.0062(16) -0.0042(19) C16 0.168(5) 0.147(4) 0.101(3) -0.051(3) -0.009(3) -0.045(4) C17 0.0556(17) 0.0454(15) 0.0539(16) -0.0027(12) -0.0030(13) -0.0082(13) C18 0.071(2) 0.0499(17) 0.077(2) -0.0041(15) 0.0032(17) -0.0087(15) C19 0.083(2) 0.0534(18) 0.082(2) -0.0177(17) -0.0056(19) 0.0036(17) C20 0.071(2) 0.074(2) 0.068(2) -0.0093(17) 0.0036(17) 0.0022(18) C21 0.077(2) 0.076(2) 0.086(2) -0.0074(18) 0.0231(19) -0.0116(18) C22 0.072(2) 0.0534(17) 0.079(2) -0.0090(15) 0.0161(17) -0.0123(15) C23 0.111(3) 0.116(3) 0.104(3) -0.030(2) 0.032(2) 0.013(3) C24 0.0532(18) 0.071(2) 0.0626(19) -0.0222(16) -0.0004(14) -0.0093(15) C25 0.088(2) 0.102(3) 0.0458(17) -0.0054(16) -0.0020(16) -0.014(2) C26 0.130(4) 0.132(3) 0.059(2) 0.005(2) -0.003(2) -0.045(3) C27 0.061(2) 0.110(3) 0.097(3) -0.017(2) 0.0210(19) -0.011(2) C28 0.164(5) 0.144(4) 0.231(6) -0.085(4) 0.130(5) -0.092(4) C29 0.065(2) 0.074(2) 0.091(2) -0.0090(18) 0.0097(18) -0.0244(17) C30 0.0564(18) 0.0518(16) 0.0568(16) -0.0108(13) 0.0034(13) -0.0114(13) C31 0.0559(17) 0.0436(14) 0.0446(14) -0.0028(11) 0.0023(12) -0.0090(12) C32 0.0638(18) 0.0464(15) 0.0437(14) -0.0014(12) -0.0019(13) -0.0118(13) C33 0.070(2) 0.0452(15) 0.0526(16) -0.0048(12) 0.0087(14) -0.0047(13) C34 0.078(2) 0.0509(16) 0.0556(17) -0.0052(14) 0.0107(15) -0.0050(14) C35 0.070(2) 0.0570(17) 0.0573(17) -0.0103(14) 0.0068(14) -0.0080(14) C36 0.068(2) 0.0685(19) 0.0551(18) -0.0059(15) 0.0018(15) -0.0139(16) C37 0.068(2) 0.082(2) 0.0556(19) -0.0111(16) -0.0087(15) -0.0060(17) C38 0.095(3) 0.119(3) 0.055(2) -0.013(2) -0.0086(19) -0.016(2) C39 0.112(3) 0.134(4) 0.064(2) 0.012(3) -0.018(2) -0.021(3) C40 0.112(3) 0.105(3) 0.091(3) 0.023(2) -0.018(2) -0.004(2) C41 0.095(3) 0.078(2) 0.076(2) 0.0022(19) -0.003(2) -0.002(2) C42 0.164(4) 0.092(3) 0.072(2) -0.035(2) 0.007(2) -0.013(3) C43 0.0530(17) 0.0470(15) 0.0442(14) -0.0009(12) -0.0025(12) -0.0075(13) C44 0.074(2) 0.0501(16) 0.0586(17) -0.0020(13) 0.0065(15) -0.0067(14) C45 0.089(2) 0.0536(17) 0.0599(18) -0.0069(14) 0.0066(17) 0.0057(17) C46 0.069(2) 0.077(2) 0.0486(17) -0.0034(15) 0.0041(15) 0.0075(17) C47 0.077(2) 0.094(3) 0.074(2) -0.0184(19) 0.0218(18) -0.0242(19) C48 0.078(2) 0.071(2) 0.071(2) -0.0221(16) 0.0173(17) -0.0226(17) C49 0.106(3) 0.112(3) 0.084(3) -0.015(2) 0.030(2) 0.015(2) C50 0.0554(19) 0.076(2) 0.0622(19) -0.0096(16) -0.0060(15) -0.0065(16) C51 0.123(4) 0.160(4) 0.080(3) 0.054(3) -0.032(3) -0.049(3) C52 0.132(4) 0.247(6) 0.076(3) 0.036(3) -0.002(3) -0.058(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 C1 N1 1.461(4) . ? C1 C2 1.464(5) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? N1 C7 1.472(3) . ? N1 C4 1.479(3) . ? O1 C15 1.378(4) . ? O1 C16 1.417(4) . ? C2 C3 1.466(5) . ? C2 H2 0.9300 . ? C2 H2A 1.00(7) . ? N2 O5 1.214(3) . ? N2 O4 1.214(3) . ? N2 C6 1.504(3) . ? O2 C24 1.201(3) . ? C3 C4 1.541(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? N3 C27 1.464(4) . ? N3 C33 1.469(4) . ? N3 C30 1.474(3) . ? O3 C24 1.335(3) . ? O3 C25 1.454(3) . ? C4 C24 1.524(4) . ? C4 C5 1.560(4) . ? N4 O7 1.214(3) . ? N4 O8 1.215(3) . ? N4 C32 1.499(4) . ? C5 C17 1.515(4) . ? C5 C6 1.516(3) . ? C5 H5 0.9800 . ? C6 C7 1.537(4) . ? C6 H6 0.9800 . ? O6 C37 1.372(4) . ? O6 C42 1.404(4) . ? C7 C8 1.506(4) . ? C7 H7 0.9800 . ? C8 C9 1.315(4) . ? C8 H8 0.9300 . ? C9 C10 1.472(4) . ? C9 H9 0.9300 . ? O9 C50 1.196(3) . ? C10 C15 1.384(4) . ? C10 C11 1.389(4) . ? O10 C50 1.328(4) . ? O10 C51 1.452(4) . ? C11 C12 1.381(4) . ? C11 H11 0.9300 . ? C12 C13 1.364(6) . ? C12 H12 0.9300 . ? C13 C14 1.373(6) . ? C13 H13 0.9300 . ? C14 C15 1.391(4) . ? C14 H14 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.380(4) . ? C17 C22 1.386(4) . ? C18 C19 1.383(4) . ? C18 H18 0.9300 . ? C19 C20 1.375(5) . ? C19 H19 0.9300 . ? C20 C21 1.365(4) . ? C20 C23 1.514(5) . ? C21 C22 1.382(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C25 C26 1.452(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C28 1.433(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.426(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.540(4) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C50 1.523(4) . ? C30 C31 1.561(4) . ? C31 C43 1.510(3) . ? C31 C32 1.515(3) . ? C31 H31 0.9800 . ? C32 C33 1.546(4) . ? C32 H32 0.9800 . ? C33 C34 1.499(4) . ? C33 H33 0.9800 . ? C34 C35 1.318(3) . ? C34 H34 0.9300 . ? C35 C36 1.471(4) . ? C35 H35 0.9300 . ? C36 C37 1.387(4) . ? C36 C41 1.389(4) . ? C37 C38 1.379(4) . ? C38 C39 1.367(5) . ? C38 H38 0.9300 . ? C39 C40 1.377(5) . ? C39 H39 0.9300 . ? C40 C41 1.378(5) . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 0.9600 . ? C43 C44 1.377(3) . ? C43 C48 1.385(4) . ? C44 C45 1.382(4) . ? C44 H44 0.9300 . ? C45 C46 1.374(4) . ? C45 H45 0.9300 . ? C46 C47 1.370(4) . ? C46 C49 1.518(4) . ? C47 C48 1.385(4) . ? C47 H47 0.9300 . ? C48 H48 0.9300 . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C51 C52 1.388(6) . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 H52A 0.9600 . ? C52 H52B 0.9600 . ? C52 H52C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 106.8(3) . . ? N1 C1 H1A 110.4 . . ? C2 C1 H1A 110.4 . . ? N1 C1 H1B 110.4 . . ? C2 C1 H1B 110.4 . . ? H1A C1 H1B 108.6 . . ? C1 N1 C7 119.1(2) . . ? C1 N1 C4 108.7(2) . . ? C7 N1 C4 111.4(2) . . ? C15 O1 C16 119.1(3) . . ? C1 C2 C3 109.4(3) . . ? C1 C2 H2 125.3 . . ? C3 C2 H2 125.3 . . ? C1 C2 H2A 100(4) . . ? C3 C2 H2A 95(4) . . ? H2 C2 H2A 77.1 . . ? O5 N2 O4 124.0(3) . . ? O5 N2 C6 119.5(2) . . ? O4 N2 C6 116.5(2) . . ? C2 C3 C4 105.9(3) . . ? C2 C3 H3A 110.6 . . ? C4 C3 H3A 110.6 . . ? C2 C3 H3B 110.6 . . ? C4 C3 H3B 110.6 . . ? H3A C3 H3B 108.7 . . ? C27 N3 C33 119.6(2) . . ? C27 N3 C30 108.8(2) . . ? C33 N3 C30 112.6(2) . . ? C24 O3 C25 116.1(2) . . ? N1 C4 C24 110.3(2) . . ? N1 C4 C3 105.9(2) . . ? C24 C4 C3 110.7(2) . . ? N1 C4 C5 104.97(19) . . ? C24 C4 C5 109.3(2) . . ? C3 C4 C5 115.5(2) . . ? O7 N4 O8 122.9(3) . . ? O7 N4 C32 117.5(2) . . ? O8 N4 C32 119.5(2) . . ? C17 C5 C6 117.7(2) . . ? C17 C5 C4 116.1(2) . . ? C6 C5 C4 101.1(2) . . ? C17 C5 H5 107.0 . . ? C6 C5 H5 107.0 . . ? C4 C5 H5 107.0 . . ? N2 C6 C5 114.1(2) . . ? N2 C6 C7 110.26(19) . . ? C5 C6 C7 105.0(2) . . ? N2 C6 H6 109.1 . . ? C5 C6 H6 109.1 . . ? C7 C6 H6 109.1 . . ? C37 O6 C42 119.2(3) . . ? N1 C7 C8 117.1(2) . . ? N1 C7 C6 100.33(18) . . ? C8 C7 C6 112.7(2) . . ? N1 C7 H7 108.8 . . ? C8 C7 H7 108.8 . . ? C6 C7 H7 108.8 . . ? C9 C8 C7 123.6(3) . . ? C9 C8 H8 118.2 . . ? C7 C8 H8 118.2 . . ? C8 C9 C10 126.2(3) . . ? C8 C9 H9 116.9 . . ? C10 C9 H9 116.9 . . ? C15 C10 C11 117.9(3) . . ? C15 C10 C9 120.6(3) . . ? C11 C10 C9 121.4(3) . . ? C50 O10 C51 119.3(3) . . ? C12 C11 C10 121.3(4) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C13 C12 C11 119.4(4) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C13 C14 121.2(4) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C13 C14 C15 119.1(4) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? O1 C15 C10 115.4(3) . . ? O1 C15 C14 123.6(3) . . ? C10 C15 C14 121.0(4) . . ? O1 C16 H16A 109.5 . . ? O1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 117.0(3) . . ? C18 C17 C5 120.0(2) . . ? C22 C17 C5 123.0(2) . . ? C17 C18 C19 121.3(3) . . ? C17 C18 H18 119.4 . . ? C19 C18 H18 119.4 . . ? C20 C19 C18 121.4(3) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C21 C20 C19 117.4(3) . . ? C21 C20 C23 121.9(3) . . ? C19 C20 C23 120.8(3) . . ? C20 C21 C22 121.9(3) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C21 C22 C17 121.0(3) . . ? C21 C22 H22 119.5 . . ? C17 C22 H22 119.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O2 C24 O3 123.1(3) . . ? O2 C24 C4 124.7(3) . . ? O3 C24 C4 112.1(2) . . ? C26 C25 O3 108.3(3) . . ? C26 C25 H25A 110.0 . . ? O3 C25 H25A 110.0 . . ? C26 C25 H25B 110.0 . . ? O3 C25 H25B 110.0 . . ? H25A C25 H25B 108.4 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C28 C27 N3 106.6(3) . . ? C28 C27 H27A 110.4 . . ? N3 C27 H27A 110.4 . . ? C28 C27 H27B 110.4 . . ? N3 C27 H27B 110.4 . . ? H27A C27 H27B 108.6 . . ? C29 C28 C27 111.6(3) . . ? C29 C28 H28A 109.3 . . ? C27 C28 H28A 109.3 . . ? C29 C28 H28B 109.3 . . ? C27 C28 H28B 109.3 . . ? H28A C28 H28B 108.0 . . ? C28 C29 C30 105.9(3) . . ? C28 C29 H29A 110.6 . . ? C30 C29 H29A 110.6 . . ? C28 C29 H29B 110.6 . . ? C30 C29 H29B 110.6 . . ? H29A C29 H29B 108.7 . . ? N3 C30 C50 109.5(2) . . ? N3 C30 C29 105.4(2) . . ? C50 C30 C29 111.4(2) . . ? N3 C30 C31 104.7(2) . . ? C50 C30 C31 110.2(2) . . ? C29 C30 C31 115.3(2) . . ? C43 C31 C32 116.6(2) . . ? C43 C31 C30 116.8(2) . . ? C32 C31 C30 101.5(2) . . ? C43 C31 H31 107.1 . . ? C32 C31 H31 107.1 . . ? C30 C31 H31 107.1 . . ? N4 C32 C31 113.1(2) . . ? N4 C32 C33 110.8(2) . . ? C31 C32 C33 105.8(2) . . ? N4 C32 H32 109.0 . . ? C31 C32 H32 109.0 . . ? C33 C32 H32 109.0 . . ? N3 C33 C34 117.8(2) . . ? N3 C33 C32 101.38(19) . . ? C34 C33 C32 112.2(2) . . ? N3 C33 H33 108.3 . . ? C34 C33 H33 108.3 . . ? C32 C33 H33 108.3 . . ? C35 C34 C33 123.0(3) . . ? C35 C34 H34 118.5 . . ? C33 C34 H34 118.5 . . ? C34 C35 C36 127.0(3) . . ? C34 C35 H35 116.5 . . ? C36 C35 H35 116.5 . . ? C37 C36 C41 117.9(3) . . ? C37 C36 C35 120.1(3) . . ? C41 C36 C35 121.9(3) . . ? O6 C37 C38 124.0(3) . . ? O6 C37 C36 114.9(3) . . ? C38 C37 C36 121.1(3) . . ? C39 C38 C37 119.5(4) . . ? C39 C38 H38 120.2 . . ? C37 C38 H38 120.2 . . ? C38 C39 C40 121.1(4) . . ? C38 C39 H39 119.5 . . ? C40 C39 H39 119.5 . . ? C39 C40 C41 118.9(4) . . ? C39 C40 H40 120.6 . . ? C41 C40 H40 120.6 . . ? C40 C41 C36 121.5(3) . . ? C40 C41 H41 119.3 . . ? C36 C41 H41 119.3 . . ? O6 C42 H42A 109.5 . . ? O6 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? O6 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C44 C43 C48 116.8(2) . . ? C44 C43 C31 120.4(2) . . ? C48 C43 C31 122.8(2) . . ? C43 C44 C45 121.3(3) . . ? C43 C44 H44 119.3 . . ? C45 C44 H44 119.3 . . ? C46 C45 C44 121.8(3) . . ? C46 C45 H45 119.1 . . ? C44 C45 H45 119.1 . . ? C47 C46 C45 117.3(3) . . ? C47 C46 C49 120.9(3) . . ? C45 C46 C49 121.8(3) . . ? C46 C47 C48 121.3(3) . . ? C46 C47 H47 119.3 . . ? C48 C47 H47 119.3 . . ? C43 C48 C47 121.6(3) . . ? C43 C48 H48 119.2 . . ? C47 C48 H48 119.2 . . ? C46 C49 H49A 109.5 . . ? C46 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C46 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? O9 C50 O10 123.1(3) . . ? O9 C50 C30 125.0(3) . . ? O10 C50 C30 111.9(2) . . ? C52 C51 O10 112.3(4) . . ? C52 C51 H51A 109.1 . . ? O10 C51 H51A 109.1 . . ? C52 C51 H51B 109.1 . . ? O10 C51 H51B 109.1 . . ? H51A C51 H51B 107.9 . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 23.95 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.344 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 921617' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_ts324 #TrackingRef 'TS324.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H24 N2 O6' _chemical_formula_sum 'C27 H24 N2 O6' _chemical_formula_weight 472.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P12(1)/c1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.131(7) _cell_length_b 16.402(9) _cell_length_c 11.331(6) _cell_angle_alpha 90.00 _cell_angle_beta 109.361(7) _cell_angle_gamma 90.00 _cell_volume 2302(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(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 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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_reflns_number 27624 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 23.74 _reflns_number_total 3453 _reflns_number_gt 2557 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0641P)^2^+1.5934P] 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 3453 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0716 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1466 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.189 _refine_ls_shift/su_mean 0.003 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 0.66919(16) 0.91074(12) 0.8425(2) 0.0775(7) Uani 1 1 d . . . O2 O 1.12771(16) 0.84808(13) 0.84796(18) 0.0640(5) Uani 1 1 d . . . O3 O 1.25621(14) 0.78548(12) 1.21511(17) 0.0603(5) Uani 1 1 d . . . O4 O 0.7419(2) 0.68755(14) 1.0855(3) 0.0940(8) Uani 1 1 d . . . O5 O 1.03142(18) 0.64722(13) 0.9584(2) 0.0822(7) Uani 1 1 d . . . O6 O 0.82362(16) 0.98044(13) 0.8944(2) 0.0811(7) Uani 1 1 d . . . N1 N 0.93040(15) 0.85887(12) 1.07467(19) 0.0459(5) Uani 1 1 d . . . N2 N 0.89192(19) 0.65281(13) 1.0374(2) 0.0590(6) Uani 1 1 d . . . C1 C 0.3006(3) 0.9053(3) 0.5404(4) 0.0921(12) Uani 1 1 d . . . H1 H 0.2308 0.8904 0.4927 0.111 Uiso 1 1 calc R . . C2 C 0.3171(4) 0.9467(3) 0.6460(5) 0.1157(16) Uani 1 1 d . . . H2 H 0.2594 0.9601 0.6727 0.139 Uiso 1 1 calc R . . C3 C 0.4242(4) 0.9700(3) 0.7178(4) 0.1011(13) Uani 1 1 d . . . H3 H 0.4372 0.9994 0.7916 0.121 Uiso 1 1 calc R . . C4 C 0.5080(2) 0.94883(17) 0.6771(3) 0.0594(8) Uani 1 1 d . . . C5 C 0.6221(3) 0.9725(2) 0.7465(4) 0.1111(16) Uani 1 1 d . . . H5A H 0.6629 0.9757 0.6894 0.133 Uiso 1 1 calc R . . H5B H 0.6240 1.0255 0.7853 0.133 Uiso 1 1 calc R . . C6 C 0.7726(2) 0.92336(17) 0.9096(3) 0.0564(7) Uani 1 1 d . . . C7 C 0.81478(19) 0.85667(15) 1.0104(3) 0.0488(6) Uani 1 1 d . . . C8 C 0.98281(19) 0.83754(15) 0.9840(2) 0.0469(6) Uani 1 1 d . . . H8 H 0.9725 0.8827 0.9245 0.056 Uiso 1 1 calc R . . C9 C 1.10157(19) 0.82123(15) 1.0402(2) 0.0440(6) Uani 1 1 d . . . C10 C 1.1676(2) 0.83253(15) 0.9611(2) 0.0472(6) Uani 1 1 d . . . C11 C 1.2842(2) 0.82458(15) 1.0238(2) 0.0483(6) Uani 1 1 d . . . C12 C 1.3239(2) 0.80051(17) 1.1475(3) 0.0530(7) Uani 1 1 d . . . C13 C 1.4335(2) 0.7899(2) 1.2097(3) 0.0685(8) Uani 1 1 d . . . H13 H 1.4586 0.7729 1.2926 0.082 Uiso 1 1 calc R . . C14 C 1.5037(2) 0.8050(2) 1.1461(4) 0.0788(10) Uani 1 1 d . . . H14 H 1.5774 0.7981 1.1865 0.095 Uiso 1 1 calc R . . C15 C 0.4835(3) 0.9059(2) 0.5682(3) 0.0736(9) Uani 1 1 d . . . H15 H 0.5387 0.8904 0.5386 0.088 Uiso 1 1 calc R . . C16 C 0.3810(4) 0.8853(2) 0.5025(4) 0.0877(11) Uani 1 1 d . . . H16 H 0.3672 0.8562 0.4284 0.105 Uiso 1 1 calc R . . C17 C 1.1486(2) 0.79816(17) 1.1589(3) 0.0540(7) Uani 1 1 d . . . H17 H 1.1041 0.7901 1.2070 0.065 Uiso 1 1 calc R . . C18 C 1.4671(2) 0.8303(2) 1.0229(4) 0.0763(9) Uani 1 1 d . . . H18 H 1.5159 0.8410 0.9814 0.092 Uiso 1 1 calc R . . C19 C 1.3585(2) 0.83958(18) 0.9620(3) 0.0634(8) Uani 1 1 d . . . H19 H 1.3340 0.8560 0.8787 0.076 Uiso 1 1 calc R . . C20 C 0.9100(2) 0.76415(16) 0.9152(2) 0.0534(7) Uani 1 1 d . . . H20 H 0.8965 0.7658 0.8248 0.064 Uiso 1 1 calc R . . C21 C 0.8041(2) 0.77293(16) 0.9457(3) 0.0542(7) Uani 1 1 d . . . H21 H 0.7407 0.7709 0.8697 0.065 Uiso 1 1 calc R . . C22 C 0.8056(2) 0.70169(17) 1.0318(3) 0.0633(8) Uani 1 1 d . . . C23 C 0.9170(3) 0.57634(18) 1.1087(3) 0.0811(10) Uani 1 1 d . . . H23A H 0.8600 0.5638 1.1414 0.122 Uiso 1 1 calc R . . H23B H 0.9837 0.5822 1.1766 0.122 Uiso 1 1 calc R . . H23C H 0.9236 0.5330 1.0548 0.122 Uiso 1 1 calc R . . C24 C 0.9544(2) 0.68254(18) 0.9699(3) 0.0588(8) Uani 1 1 d . . . C25 C 0.9568(2) 0.93073(16) 1.1559(3) 0.0560(7) Uani 1 1 d . . . H25A H 0.9712 0.9777 1.1119 0.067 Uiso 1 1 calc R . . H25B H 1.0190 0.9207 1.2298 0.067 Uiso 1 1 calc R . . C26 C 0.8541(2) 0.94308(18) 1.1902(3) 0.0608(7) Uani 1 1 d . . . H26A H 0.8247 0.9972 1.1660 0.073 Uiso 1 1 calc R . . H26B H 0.8698 0.9368 1.2796 0.073 Uiso 1 1 calc R . . C27 C 0.7731(2) 0.87729(18) 1.1180(3) 0.0614(8) Uani 1 1 d . . . H27A H 0.7749 0.8300 1.1700 0.074 Uiso 1 1 calc R . . H27B H 0.7001 0.8986 1.0871 0.074 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0548(12) 0.0626(13) 0.0931(16) 0.0321(11) -0.0049(11) -0.0075(10) O2 0.0648(13) 0.0774(14) 0.0493(12) 0.0052(10) 0.0184(10) 0.0078(10) O3 0.0405(10) 0.0829(14) 0.0519(11) 0.0121(10) 0.0078(9) 0.0008(9) O4 0.0884(17) 0.0624(14) 0.147(2) 0.0184(14) 0.0609(17) -0.0101(12) O5 0.0680(15) 0.0661(14) 0.1078(18) -0.0201(12) 0.0230(13) 0.0078(11) O6 0.0587(13) 0.0623(13) 0.1101(18) 0.0310(12) 0.0115(12) -0.0118(11) N1 0.0359(11) 0.0477(12) 0.0525(13) -0.0025(10) 0.0125(10) -0.0049(9) N2 0.0584(15) 0.0452(13) 0.0642(15) 0.0014(11) 0.0077(12) -0.0017(11) C1 0.066(2) 0.098(3) 0.095(3) 0.030(2) 0.004(2) -0.001(2) C2 0.076(3) 0.156(4) 0.132(4) 0.026(4) 0.057(3) 0.046(3) C3 0.117(3) 0.114(3) 0.068(2) -0.013(2) 0.026(2) 0.030(3) C4 0.0554(17) 0.0484(16) 0.0647(19) 0.0182(14) 0.0068(15) 0.0078(13) C5 0.076(2) 0.081(2) 0.132(3) 0.059(2) -0.024(2) -0.0163(19) C6 0.0424(15) 0.0520(17) 0.0706(18) 0.0071(14) 0.0131(14) -0.0030(13) C7 0.0367(14) 0.0436(14) 0.0620(16) 0.0073(12) 0.0110(12) -0.0022(11) C8 0.0403(14) 0.0500(15) 0.0475(15) 0.0030(12) 0.0108(12) -0.0010(11) C9 0.0396(14) 0.0439(14) 0.0472(15) 0.0000(11) 0.0128(12) -0.0029(11) C10 0.0482(15) 0.0420(14) 0.0497(16) -0.0019(11) 0.0138(13) 0.0007(11) C11 0.0439(15) 0.0476(15) 0.0544(16) -0.0056(12) 0.0174(12) -0.0046(11) C12 0.0423(15) 0.0560(16) 0.0613(17) -0.0044(13) 0.0181(13) -0.0043(12) C13 0.0474(17) 0.080(2) 0.070(2) 0.0047(16) 0.0084(15) -0.0003(15) C14 0.0424(17) 0.100(3) 0.090(3) -0.005(2) 0.0158(17) -0.0068(17) C15 0.076(2) 0.069(2) 0.082(2) 0.0058(18) 0.0346(19) 0.0113(17) C16 0.099(3) 0.077(2) 0.075(2) -0.0039(18) 0.013(2) -0.005(2) C17 0.0436(15) 0.0644(17) 0.0536(16) 0.0060(13) 0.0156(13) -0.0043(13) C18 0.0520(19) 0.092(2) 0.092(3) -0.011(2) 0.0331(18) -0.0129(17) C19 0.0577(19) 0.072(2) 0.0664(19) -0.0068(15) 0.0287(16) -0.0079(15) C20 0.0525(16) 0.0552(16) 0.0460(15) -0.0024(12) 0.0076(13) -0.0037(13) C21 0.0404(14) 0.0504(16) 0.0613(17) 0.0017(13) 0.0027(12) -0.0051(12) C22 0.0541(18) 0.0452(16) 0.086(2) 0.0024(15) 0.0168(16) -0.0094(14) C23 0.097(3) 0.0458(17) 0.084(2) 0.0075(16) 0.0079(19) 0.0050(16) C24 0.0481(16) 0.0535(17) 0.0623(18) -0.0137(14) 0.0014(14) -0.0006(14) C25 0.0548(16) 0.0514(16) 0.0617(17) -0.0102(13) 0.0190(14) -0.0063(13) C26 0.0607(18) 0.0583(17) 0.0683(18) 0.0037(14) 0.0280(15) 0.0039(14) C27 0.0486(16) 0.0596(18) 0.080(2) 0.0153(15) 0.0270(15) 0.0060(13) _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 C6 1.335(3) . ? O1 C5 1.464(4) . ? O2 C10 1.240(3) . ? O3 C17 1.360(3) . ? O3 C12 1.374(3) . ? O4 C22 1.210(4) . ? O5 C24 1.209(3) . ? O6 C6 1.196(3) . ? N1 C7 1.450(3) . ? N1 C8 1.456(3) . ? N1 C25 1.465(3) . ? N2 C22 1.372(4) . ? N2 C24 1.383(4) . ? N2 C23 1.469(4) . ? C1 C16 1.306(5) . ? C1 C2 1.329(6) . ? C1 H1 0.9300 . ? C2 C3 1.424(6) . ? C2 H2 0.9300 . ? C3 C4 1.372(5) . ? C3 H3 0.9300 . ? C4 C15 1.364(4) . ? C4 C5 1.494(4) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.545(4) . ? C7 C27 1.530(4) . ? C7 C21 1.541(4) . ? C8 C9 1.500(3) . ? C8 C20 1.574(4) . ? C8 H8 0.9800 . ? C9 C17 1.335(4) . ? C9 C10 1.451(4) . ? C10 C11 1.464(4) . ? C11 C12 1.382(4) . ? C11 C19 1.399(4) . ? C12 C13 1.387(4) . ? C13 C14 1.368(4) . ? C13 H13 0.9300 . ? C14 C18 1.380(5) . ? C14 H14 0.9300 . ? C15 C16 1.346(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.371(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C24 1.509(4) . ? C20 C21 1.547(4) . ? C20 H20 0.9800 . ? C21 C22 1.518(4) . ? C21 H21 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C25 C26 1.536(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.545(4) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 O1 C5 114.6(2) . . ? C17 O3 C12 118.4(2) . . ? C7 N1 C8 107.5(2) . . ? C7 N1 C25 109.0(2) . . ? C8 N1 C25 124.6(2) . . ? C22 N2 C24 113.6(2) . . ? C22 N2 C23 123.7(3) . . ? C24 N2 C23 122.7(3) . . ? C16 C1 C2 121.1(4) . . ? C16 C1 H1 119.5 . . ? C2 C1 H1 119.5 . . ? C1 C2 C3 119.1(4) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 119.4(4) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C15 C4 C3 117.4(3) . . ? C15 C4 C5 120.4(3) . . ? C3 C4 C5 122.2(4) . . ? O1 C5 C4 108.3(2) . . ? O1 C5 H5A 110.0 . . ? C4 C5 H5A 110.0 . . ? O1 C5 H5B 110.0 . . ? C4 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? O6 C6 O1 123.5(3) . . ? O6 C6 C7 125.5(2) . . ? O1 C6 C7 111.0(2) . . ? N1 C7 C27 100.7(2) . . ? N1 C7 C21 100.14(19) . . ? C27 C7 C21 125.2(2) . . ? N1 C7 C6 114.3(2) . . ? C27 C7 C6 107.3(2) . . ? C21 C7 C6 109.0(2) . . ? N1 C8 C9 114.3(2) . . ? N1 C8 C20 100.49(19) . . ? C9 C8 C20 116.7(2) . . ? N1 C8 H8 108.3 . . ? C9 C8 H8 108.3 . . ? C20 C8 H8 108.3 . . ? C17 C9 C10 119.2(2) . . ? C17 C9 C8 123.1(2) . . ? C10 C9 C8 117.7(2) . . ? O2 C10 C9 122.1(2) . . ? O2 C10 C11 122.4(2) . . ? C9 C10 C11 115.6(2) . . ? C12 C11 C19 117.9(3) . . ? C12 C11 C10 120.0(2) . . ? C19 C11 C10 122.1(3) . . ? O3 C12 C11 121.3(2) . . ? O3 C12 C13 116.6(3) . . ? C11 C12 C13 122.0(3) . . ? C14 C13 C12 118.5(3) . . ? C14 C13 H13 120.8 . . ? C12 C13 H13 120.8 . . ? C13 C14 C18 121.1(3) . . ? C13 C14 H14 119.4 . . ? C18 C14 H14 119.4 . . ? C16 C15 C4 121.5(3) . . ? C16 C15 H15 119.2 . . ? C4 C15 H15 119.2 . . ? C1 C16 C15 121.6(4) . . ? C1 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? C9 C17 O3 125.2(2) . . ? C9 C17 H17 117.4 . . ? O3 C17 H17 117.4 . . ? C19 C18 C14 119.9(3) . . ? C19 C18 H18 120.0 . . ? C14 C18 H18 120.0 . . ? C18 C19 C11 120.6(3) . . ? C18 C19 H19 119.7 . . ? C11 C19 H19 119.7 . . ? C24 C20 C21 104.1(2) . . ? C24 C20 C8 112.8(2) . . ? C21 C20 C8 105.1(2) . . ? C24 C20 H20 111.5 . . ? C21 C20 H20 111.5 . . ? C8 C20 H20 111.5 . . ? C22 C21 C7 113.6(2) . . ? C22 C21 C20 104.5(2) . . ? C7 C21 C20 104.0(2) . . ? C22 C21 H21 111.4 . . ? C7 C21 H21 111.4 . . ? C20 C21 H21 111.4 . . ? O4 C22 N2 124.3(3) . . ? O4 C22 C21 127.4(3) . . ? N2 C22 C21 108.3(3) . . ? N2 C23 H23A 109.5 . . ? N2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O5 C24 N2 124.1(3) . . ? O5 C24 C20 127.1(3) . . ? N2 C24 C20 108.7(2) . . ? N1 C25 C26 102.7(2) . . ? N1 C25 H25A 111.2 . . ? C26 C25 H25A 111.2 . . ? N1 C25 H25B 111.2 . . ? C26 C25 H25B 111.2 . . ? H25A C25 H25B 109.1 . . ? C25 C26 C27 106.4(2) . . ? C25 C26 H26A 110.5 . . ? C27 C26 H26A 110.5 . . ? C25 C26 H26B 110.5 . . ? C27 C26 H26B 110.5 . . ? H26A C26 H26B 108.6 . . ? C7 C27 C26 102.2(2) . . ? C7 C27 H27A 111.3 . . ? C26 C27 H27A 111.3 . . ? C7 C27 H27B 111.3 . . ? C26 C27 H27B 111.3 . . ? H27A C27 H27B 109.2 . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 23.74 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.222 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.038 _atom_sites_special_details ; The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual = -1, Ralpha = 0.046 ; _database_code_depnum_ccdc_archive 'CCDC 921618'