Supplementary Material for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 # 1. SUBMISSION DETAILS _publ_contact_author_name 'Muller, Thomas J.J.' _publ_contact_author_address ; Institut fur Makromolekulare Chemie und Organische Chemie Heinrich-Heine-Universitat Dusseldorf Universitatsstrasse 1 D-40225 Dusseldorf Germany ; _publ_contact_author_phone '+49 211 - 8112298' _publ_contact_author_fax '+49 211 - 8114324' _publ_contact_author_email ThomasJJ.Mueller@uni-duesseldorf.de _publ_requested_coeditor_name ? _publ_contact_letter ; paper submitted for publication Organic and Biomolecular Chemistry ; #======================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Dichotomies in microwave-assisted propargyl- isomerization-Claisen domino sequences dependent on base strengths ; loop_ _publ_author_name _publ_author_address D.M.D'Souza ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; W.-W.Liao ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; F.Rominger ; Organisch-Chemisches Institut Universitat Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Bundesrepublik Deutschland ; T.J.J.Muller ; Institut fur Organische Chemie und Makromolekulare Chemie Heinrich Heine Universitat Dusseldorf Universitatsstra\se 1 40225 Dusseldorf Bundesrepublik Deutschland ; # Attachment 'DDS_OBC_07_komplett.cif' #====================================================================== data_dds52 _database_code_depnum_ccdc_archive 'CCDC 641143' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'in paper 2c' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H25 N O' _chemical_formula_weight 475.56 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 12.1762(2) _cell_length_b 17.4387(2) _cell_length_c 20.1060(1) _cell_angle_alpha 80.239(1) _cell_angle_beta 73.766(1) _cell_angle_gamma 73.137(1) _cell_volume 3904.56(8) _cell_formula_units_Z 6 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1500 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9717 _exptl_absorpt_correction_T_max 0.9942 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26587 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 22.72 _reflns_number_total 10487 _reflns_number_gt 7415 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+0.8682P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10487 _refine_ls_number_parameters 1000 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1238 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O9 O -0.17672(16) 0.23836(11) 0.21528(10) 0.0562(5) Uani 1 1 d . . . N27 N -0.0174(3) -0.24996(16) 0.20829(14) 0.0716(8) Uani 1 1 d . . . C1 C 0.0773(2) 0.18711(14) 0.20746(13) 0.0358(6) Uani 1 1 d . . . H1 H 0.0254 0.2134 0.2499 0.043 Uiso 1 1 calc R . . C2 C 0.0197(2) 0.19058(13) 0.14888(12) 0.0310(6) Uani 1 1 d . . . C3 C 0.08260(19) 0.12496(13) 0.09973(12) 0.0286(6) Uani 1 1 d . . . H3 H 0.0663 0.1459 0.0530 0.034 Uiso 1 1 calc R . . C4 C 0.2165(2) 0.11861(13) 0.09447(12) 0.0290(6) Uani 1 1 d . . . H4 H 0.2722 0.0910 0.0536 0.035 Uiso 1 1 calc R . . C5 C 0.2163(2) 0.20694(13) 0.09143(12) 0.0271(6) Uani 1 1 d . . . C6 C 0.1052(2) 0.24312(14) 0.14090(12) 0.0323(6) Uani 1 1 d . . . H6 H 0.0753 0.3029 0.1413 0.039 Uiso 1 1 calc R . . C7 C 0.2430(2) 0.07997(14) 0.16298(13) 0.0347(6) Uani 1 1 d . . . H7 H 0.3061 0.0334 0.1662 0.042 Uiso 1 1 calc R . . C8 C 0.1726(2) 0.11525(15) 0.21849(13) 0.0381(6) Uani 1 1 d . . . H8 H 0.1831 0.0950 0.2638 0.046 Uiso 1 1 calc R . . C9 C -0.1104(2) 0.22629(14) 0.15813(15) 0.0383(7) Uani 1 1 d . . . C10 C -0.1556(2) 0.24527(15) 0.09342(15) 0.0409(7) Uani 1 1 d . . . C11 C -0.2619(3) 0.22846(18) 0.0945(2) 0.0649(9) Uani 1 1 d . . . H11 H -0.3069 0.2066 0.1361 0.078 Uiso 1 1 calc R . . C12 C -0.3007(3) 0.2447(2) 0.0324(2) 0.0700(10) Uani 1 1 d . . . H12 H -0.3709 0.2317 0.0317 0.084 Uiso 1 1 calc R . . C13 C -0.2378(3) 0.2791(2) -0.0267(2) 0.0726(10) Uani 1 1 d . . . H13 H -0.2658 0.2904 -0.0679 0.087 Uiso 1 1 calc R . . C14 C -0.1362(3) 0.29716(17) -0.02765(17) 0.0581(8) Uani 1 1 d . . . H14 H -0.0940 0.3219 -0.0688 0.070 Uiso 1 1 calc R . . C15 C -0.0947(2) 0.27904(15) 0.03241(15) 0.0439(7) Uani 1 1 d . . . H15 H -0.0223 0.2902 0.0314 0.053 Uiso 1 1 calc R . . C21 C 0.04863(19) 0.04602(13) 0.12207(12) 0.0290(6) Uani 1 1 d . . . C22 C -0.0018(2) 0.02384(15) 0.19105(13) 0.0417(7) Uani 1 1 d . . . H22 H -0.0239 0.0615 0.2245 0.050 Uiso 1 1 calc R . . C23 C -0.0205(2) -0.05192(16) 0.21186(14) 0.0435(7) Uani 1 1 d . . . H23 H -0.0532 -0.0665 0.2595 0.052 Uiso 1 1 calc R . . C24 C 0.0085(2) -0.10651(15) 0.16324(14) 0.0370(6) Uani 1 1 d . . . C25 C 0.0542(2) -0.08421(14) 0.09349(13) 0.0374(6) Uani 1 1 d . . . H25 H 0.0718 -0.1208 0.0596 0.045 Uiso 1 1 calc R . . C26 C 0.0738(2) -0.00858(14) 0.07371(13) 0.0330(6) Uani 1 1 d . . . H26 H 0.1051 0.0064 0.0260 0.040 Uiso 1 1 calc R . . C27 C -0.0060(3) -0.18660(17) 0.18705(15) 0.0493(7) Uani 1 1 d . . . C30 C 0.3019(2) 0.24281(13) 0.05586(12) 0.0282(6) Uani 1 1 d . . . C31 C 0.4161(2) 0.19824(13) 0.01175(13) 0.0299(6) Uani 1 1 d . . . C32 C 0.4627(2) 0.23278(15) -0.05406(13) 0.0354(6) Uani 1 1 d . . . H32 H 0.4231 0.2853 -0.0699 0.042 Uiso 1 1 calc R . . C33 C 0.5659(2) 0.19140(17) -0.09641(14) 0.0461(7) Uani 1 1 d . . . H33 H 0.5953 0.2150 -0.1417 0.055 Uiso 1 1 calc R . . C34 C 0.6263(2) 0.11641(17) -0.07360(17) 0.0516(8) Uani 1 1 d . . . H34 H 0.6970 0.0881 -0.1030 0.062 Uiso 1 1 calc R . . C35 C 0.5837(2) 0.08260(16) -0.00810(17) 0.0536(8) Uani 1 1 d . . . H35 H 0.6259 0.0312 0.0083 0.064 Uiso 1 1 calc R . . C36 C 0.4795(2) 0.12319(15) 0.03409(15) 0.0413(7) Uani 1 1 d . . . H36 H 0.4509 0.0991 0.0793 0.050 Uiso 1 1 calc R . . C41 C 0.2913(2) 0.32918(13) 0.06202(12) 0.0288(6) Uani 1 1 d . . . C42 C 0.1983(2) 0.39174(14) 0.04665(12) 0.0340(6) Uani 1 1 d . . . H42 H 0.1389 0.3804 0.0306 0.041 Uiso 1 1 calc R . . C43 C 0.1915(2) 0.47034(15) 0.05444(14) 0.0448(7) Uani 1 1 d . . . H43 H 0.1281 0.5125 0.0431 0.054 Uiso 1 1 calc R . . C44 C 0.2758(3) 0.48808(16) 0.07849(14) 0.0493(8) Uani 1 1 d . . . H44 H 0.2703 0.5422 0.0841 0.059 Uiso 1 1 calc R . . C45 C 0.3681(3) 0.42672(17) 0.09443(14) 0.0496(8) Uani 1 1 d . . . H45 H 0.4263 0.4384 0.1114 0.059 Uiso 1 1 calc R . . C46 C 0.3761(2) 0.34841(15) 0.08571(13) 0.0393(7) Uani 1 1 d . . . H46 H 0.4408 0.3067 0.0961 0.047 Uiso 1 1 calc R . . O9A O 0.90909(15) 0.41845(10) 0.11982(9) 0.0436(5) Uani 1 1 d . . . N27A N 0.7858(2) 0.89952(14) 0.08080(12) 0.0552(7) Uani 1 1 d . . . C1A C 0.6591(2) 0.46650(14) 0.12438(12) 0.0315(6) Uani 1 1 d . . . H1A H 0.7128 0.4351 0.0852 0.038 Uiso 1 1 calc R . . C2A C 0.71247(19) 0.46979(13) 0.18323(12) 0.0273(6) Uani 1 1 d . . . C3A C 0.64802(19) 0.54143(13) 0.22529(12) 0.0272(6) Uani 1 1 d . . . H3A H 0.6602 0.5264 0.2734 0.033 Uiso 1 1 calc R . . C4A C 0.5149(2) 0.54808(13) 0.22876(12) 0.0305(6) Uani 1 1 d . . . H4A H 0.4579 0.5808 0.2663 0.037 Uiso 1 1 calc R . . C5A C 0.5136(2) 0.45963(13) 0.24096(12) 0.0286(6) Uani 1 1 d . . . C6A C 0.6253(2) 0.41771(14) 0.19512(12) 0.0299(6) Uani 1 1 d . . . H6A H 0.6533 0.3576 0.1999 0.036 Uiso 1 1 calc R . . C7A C 0.5681(2) 0.53785(14) 0.10608(13) 0.0354(6) Uani 1 1 d . . . H7A H 0.5627 0.5535 0.0593 0.042 Uiso 1 1 calc R . . C8A C 0.4945(2) 0.57911(14) 0.15766(13) 0.0351(6) Uani 1 1 d . . . H8A H 0.4329 0.6252 0.1502 0.042 Uiso 1 1 calc R . . C9A C 0.8417(2) 0.43301(13) 0.17642(13) 0.0301(6) Uani 1 1 d . . . C10A C 0.8872(2) 0.41603(14) 0.23980(13) 0.0343(6) Uani 1 1 d . . . C11A C 0.9958(2) 0.43000(16) 0.23642(17) 0.0525(8) Uani 1 1 d . . . H11A H 1.0393 0.4507 0.1936 0.063 Uiso 1 1 calc R . . C12A C 1.0407(3) 0.4141(2) 0.2945(2) 0.0739(10) Uani 1 1 d . . . H12A H 1.1135 0.4254 0.2923 0.089 Uiso 1 1 calc R . . C13A C 0.9787(4) 0.3816(2) 0.3558(2) 0.0820(12) Uani 1 1 d . . . H13A H 1.0100 0.3696 0.3957 0.098 Uiso 1 1 calc R . . C14A C 0.8727(3) 0.36632(18) 0.35994(17) 0.0675(10) Uani 1 1 d . . . H14A H 0.8314 0.3433 0.4024 0.081 Uiso 1 1 calc R . . C15A C 0.8259(3) 0.38444(15) 0.30236(14) 0.0460(7) Uani 1 1 d . . . H15A H 0.7514 0.3752 0.3056 0.055 Uiso 1 1 calc R . . C21A C 0.6863(2) 0.61840(13) 0.19625(12) 0.0280(6) Uani 1 1 d . . . C22A C 0.7688(2) 0.62403(14) 0.13332(12) 0.0335(6) Uani 1 1 d . . . H22A H 0.8060 0.5779 0.1084 0.040 Uiso 1 1 calc R . . C23A C 0.7975(2) 0.69620(15) 0.10636(13) 0.0366(6) Uani 1 1 d . . . H23A H 0.8546 0.6990 0.0634 0.044 Uiso 1 1 calc R . . C24A C 0.7436(2) 0.76399(14) 0.14154(13) 0.0328(6) Uani 1 1 d . . . C25A C 0.6637(2) 0.75912(15) 0.20560(13) 0.0385(6) Uani 1 1 d . . . H25A H 0.6280 0.8051 0.2308 0.046 Uiso 1 1 calc R . . C26A C 0.6367(2) 0.68647(14) 0.23242(13) 0.0354(6) Uani 1 1 d . . . H26A H 0.5829 0.6830 0.2767 0.042 Uiso 1 1 calc R . . C27A C 0.7677(2) 0.83983(16) 0.10884(14) 0.0400(7) Uani 1 1 d . . . C30A C 0.4303(2) 0.42631(13) 0.28373(12) 0.0311(6) Uani 1 1 d . . . C31A C 0.3157(2) 0.47391(14) 0.32400(13) 0.0335(6) Uani 1 1 d . . . C32A C 0.2717(2) 0.44984(16) 0.39379(14) 0.0454(7) Uani 1 1 d . . . H32A H 0.3153 0.4029 0.4158 0.054 Uiso 1 1 calc R . . C33A C 0.1651(3) 0.49374(18) 0.43126(16) 0.0568(8) Uani 1 1 d . . . H33A H 0.1369 0.4776 0.4791 0.068 Uiso 1 1 calc R . . C34A C 0.0996(3) 0.56080(17) 0.39955(18) 0.0600(9) Uani 1 1 d . . . H34A H 0.0260 0.5905 0.4254 0.072 Uiso 1 1 calc R . . C35A C 0.1409(2) 0.58455(17) 0.33085(17) 0.0567(8) Uani 1 1 d . . . H35A H 0.0958 0.6307 0.3089 0.068 Uiso 1 1 calc R . . C36A C 0.2478(2) 0.54156(15) 0.29331(15) 0.0434(7) Uani 1 1 d . . . H36A H 0.2754 0.5585 0.2456 0.052 Uiso 1 1 calc R . . C41A C 0.4475(2) 0.33698(14) 0.29181(14) 0.0398(7) Uani 1 1 d . . . C42A C 0.5266(3) 0.28677(17) 0.32843(19) 0.0691(10) Uani 1 1 d . . . H42A H 0.5702 0.3090 0.3492 0.083 Uiso 1 1 calc R . . C43A C 0.5422(3) 0.2035(2) 0.3348(3) 0.1006(16) Uani 1 1 d . . . H43A H 0.5965 0.1691 0.3598 0.121 Uiso 1 1 calc R . . C44A C 0.4798(4) 0.1715(2) 0.3052(2) 0.0952(16) Uani 1 1 d . . . H44A H 0.4908 0.1148 0.3098 0.114 Uiso 1 1 calc R . . C45A C 0.4011(4) 0.2200(2) 0.26880(18) 0.0837(13) Uani 1 1 d . . . H45A H 0.3587 0.1972 0.2478 0.100 Uiso 1 1 calc R . . C46A C 0.3841(3) 0.30318(17) 0.26307(15) 0.0579(8) Uani 1 1 d . . . H46A H 0.3281 0.3371 0.2390 0.070 Uiso 1 1 calc R . . O9B O 0.47437(16) 0.92800(11) 0.47467(10) 0.0514(5) Uani 1 1 d . . . N27B N 0.5836(3) 0.45422(19) 0.42241(15) 0.0955(12) Uani 1 1 d . . . C1B C 0.6946(2) 0.86084(14) 0.51487(12) 0.0334(6) Uani 1 1 d . . . H1B H 0.6255 0.8911 0.5490 0.040 Uiso 1 1 calc R . . C2B C 0.6805(2) 0.86795(13) 0.44165(12) 0.0301(6) Uani 1 1 d . . . C3B C 0.7630(2) 0.79929(13) 0.39939(12) 0.0301(6) Uani 1 1 d . . . H3B H 0.7802 0.8207 0.3492 0.036 Uiso 1 1 calc R . . C4B C 0.8786(2) 0.78272(14) 0.42523(12) 0.0321(6) Uani 1 1 d . . . H4B H 0.9498 0.7506 0.3936 0.039 Uiso 1 1 calc R . . C5B C 0.8857(2) 0.86810(14) 0.42705(12) 0.0305(6) Uani 1 1 d . . . C6B C 0.7615(2) 0.91223(14) 0.45712(12) 0.0315(6) Uani 1 1 d . . . H6B H 0.7385 0.9722 0.4561 0.038 Uiso 1 1 calc R . . C7B C 0.7627(2) 0.78359(15) 0.54286(13) 0.0378(6) Uani 1 1 d . . . H7B H 0.7409 0.7636 0.5903 0.045 Uiso 1 1 calc R . . C8B C 0.8555(2) 0.74363(15) 0.49861(13) 0.0363(6) Uani 1 1 d . . . H8B H 0.9043 0.6935 0.5123 0.044 Uiso 1 1 calc R . . C9B C 0.5632(2) 0.91261(14) 0.42726(14) 0.0352(6) Uani 1 1 d . . . C10B C 0.5566(2) 0.93653(14) 0.35386(14) 0.0368(6) Uani 1 1 d . . . C11B C 0.6495(2) 0.95711(14) 0.30258(14) 0.0421(7) Uani 1 1 d . . . H11B H 0.7206 0.9557 0.3142 0.050 Uiso 1 1 calc R . . C12B C 0.6393(3) 0.97979(15) 0.23434(15) 0.0516(8) Uani 1 1 d . . . H12B H 0.7024 0.9947 0.1995 0.062 Uiso 1 1 calc R . . C13B C 0.5357(3) 0.98030(17) 0.21797(17) 0.0617(9) Uani 1 1 d . . . H13B H 0.5283 0.9950 0.1714 0.074 Uiso 1 1 calc R . . C14B C 0.4439(3) 0.95975(19) 0.26843(19) 0.0679(9) Uani 1 1 d . . . H14B H 0.3735 0.9603 0.2565 0.082 Uiso 1 1 calc R . . C15B C 0.4531(3) 0.93857(16) 0.33561(16) 0.0518(8) Uani 1 1 d . . . H15B H 0.3886 0.9251 0.3702 0.062 Uiso 1 1 calc R . . C21B C 0.7196(2) 0.72516(14) 0.40553(12) 0.0296(6) Uani 1 1 d . . . C22B C 0.6148(2) 0.71547(15) 0.45150(13) 0.0396(7) Uani 1 1 d . . . H22B H 0.5669 0.7573 0.4797 0.048 Uiso 1 1 calc R . . C23B C 0.5788(2) 0.64579(15) 0.45688(14) 0.0447(7) Uani 1 1 d . . . H23B H 0.5065 0.6401 0.4883 0.054 Uiso 1 1 calc R . . C24B C 0.6487(2) 0.58441(15) 0.41629(13) 0.0418(7) Uani 1 1 d . . . C25B C 0.7541(2) 0.59311(15) 0.37020(13) 0.0420(7) Uani 1 1 d . . . H25B H 0.8028 0.5508 0.3428 0.050 Uiso 1 1 calc R . . C26B C 0.7875(2) 0.66332(14) 0.36446(13) 0.0357(6) Uani 1 1 d . . . H26B H 0.8585 0.6696 0.3318 0.043 Uiso 1 1 calc R . . C27B C 0.6116(3) 0.51190(19) 0.42115(15) 0.0610(9) Uani 1 1 d . . . C30B C 0.9850(2) 0.89405(14) 0.40560(12) 0.0330(6) Uani 1 1 d . . . C31B C 1.1029(2) 0.83366(16) 0.38922(13) 0.0388(7) Uani 1 1 d . . . C32B C 1.1344(2) 0.77044(17) 0.43804(15) 0.0485(7) Uani 1 1 d . . . H32B H 1.0795 0.7655 0.4816 0.058 Uiso 1 1 calc R . . C33B C 1.2426(3) 0.71453(19) 0.42543(17) 0.0624(9) Uani 1 1 d . . . H33B H 1.2614 0.6717 0.4598 0.075 Uiso 1 1 calc R . . C34B C 1.3223(3) 0.7212(2) 0.36330(19) 0.0701(10) Uani 1 1 d . . . H34B H 1.3968 0.6827 0.3543 0.084 Uiso 1 1 calc R . . C35B C 1.2956(3) 0.7831(2) 0.31374(18) 0.0706(10) Uani 1 1 d . . . H35B H 1.3518 0.7874 0.2706 0.085 Uiso 1 1 calc R . . C36B C 1.1856(3) 0.84021(19) 0.32636(15) 0.0567(8) Uani 1 1 d . . . H36B H 1.1678 0.8833 0.2920 0.068 Uiso 1 1 calc R . . C41B C 0.9876(2) 0.97945(15) 0.40090(12) 0.0362(6) Uani 1 1 d . . . C42B C 1.0796(3) 0.99810(17) 0.41849(13) 0.0456(7) Uani 1 1 d . . . H42B H 1.1394 0.9559 0.4336 0.055 Uiso 1 1 calc R . . C43B C 1.0850(3) 1.0769(2) 0.41421(14) 0.0562(9) Uani 1 1 d . . . H43B H 1.1482 1.0883 0.4263 0.067 Uiso 1 1 calc R . . C44B C 0.9991(3) 1.1389(2) 0.39255(15) 0.0620(9) Uani 1 1 d . . . H44B H 1.0024 1.1930 0.3904 0.074 Uiso 1 1 calc R . . C45B C 0.9079(3) 1.12206(17) 0.37394(14) 0.0549(8) Uani 1 1 d . . . H45B H 0.8488 1.1647 0.3585 0.066 Uiso 1 1 calc R . . C46B C 0.9030(2) 1.04282(16) 0.37783(13) 0.0432(7) Uani 1 1 d . . . H46B H 0.8406 1.0317 0.3645 0.052 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 O9 0.0401(12) 0.0525(12) 0.0574(13) -0.0075(10) 0.0117(11) -0.0052(9) N27 0.096(2) 0.0478(17) 0.080(2) 0.0130(15) -0.0294(17) -0.0368(16) C1 0.0410(16) 0.0351(15) 0.0294(14) -0.0055(11) -0.0022(12) -0.0114(12) C2 0.0280(14) 0.0264(13) 0.0334(14) -0.0035(11) -0.0004(12) -0.0055(11) C3 0.0292(14) 0.0246(13) 0.0305(14) -0.0009(11) -0.0056(11) -0.0072(11) C4 0.0254(13) 0.0251(13) 0.0336(14) -0.0023(11) -0.0047(11) -0.0049(10) C5 0.0254(14) 0.0242(13) 0.0304(14) -0.0021(11) -0.0098(11) -0.0017(11) C6 0.0308(14) 0.0270(14) 0.0357(15) -0.0049(11) -0.0029(12) -0.0063(11) C7 0.0333(15) 0.0285(14) 0.0423(16) 0.0021(12) -0.0155(13) -0.0053(11) C8 0.0448(17) 0.0376(15) 0.0315(15) 0.0012(12) -0.0104(13) -0.0114(13) C9 0.0327(16) 0.0249(14) 0.0498(18) -0.0077(13) 0.0052(15) -0.0083(12) C10 0.0221(14) 0.0312(15) 0.069(2) -0.0207(14) -0.0087(14) -0.0005(11) C11 0.0361(18) 0.059(2) 0.099(3) -0.0344(19) -0.0062(19) -0.0061(15) C12 0.041(2) 0.074(2) 0.111(3) -0.040(2) -0.036(2) -0.0054(17) C13 0.068(3) 0.060(2) 0.099(3) -0.025(2) -0.042(2) 0.0015(19) C14 0.062(2) 0.0472(18) 0.069(2) -0.0128(16) -0.0314(18) -0.0024(16) C15 0.0387(16) 0.0383(16) 0.0573(19) -0.0101(14) -0.0202(15) -0.0028(13) C21 0.0236(13) 0.0292(14) 0.0328(15) -0.0027(11) -0.0068(11) -0.0048(11) C22 0.0496(17) 0.0355(16) 0.0383(16) -0.0069(13) 0.0004(14) -0.0171(13) C23 0.0504(18) 0.0451(17) 0.0360(16) 0.0019(14) -0.0031(14) -0.0243(14) C24 0.0342(15) 0.0338(15) 0.0462(17) 0.0042(13) -0.0127(13) -0.0151(12) C25 0.0417(16) 0.0319(15) 0.0407(17) -0.0061(12) -0.0100(13) -0.0114(12) C26 0.0332(15) 0.0330(15) 0.0334(15) -0.0008(12) -0.0080(12) -0.0110(11) C27 0.058(2) 0.0426(19) 0.0535(19) 0.0048(15) -0.0188(15) -0.0224(15) C30 0.0258(14) 0.0272(13) 0.0319(14) -0.0010(11) -0.0081(12) -0.0072(11) C31 0.0237(14) 0.0265(14) 0.0408(16) -0.0052(12) -0.0087(12) -0.0067(11) C32 0.0284(15) 0.0363(15) 0.0410(16) -0.0057(13) -0.0089(13) -0.0061(12) C33 0.0337(16) 0.060(2) 0.0441(17) -0.0117(15) -0.0026(14) -0.0141(15) C34 0.0280(16) 0.052(2) 0.072(2) -0.0289(17) -0.0018(16) -0.0040(14) C35 0.0336(17) 0.0335(16) 0.086(2) -0.0086(16) -0.0071(17) -0.0028(13) C36 0.0299(15) 0.0333(15) 0.0555(18) 0.0004(13) -0.0065(14) -0.0068(12) C41 0.0281(14) 0.0276(14) 0.0282(14) -0.0050(11) -0.0008(11) -0.0077(11) C42 0.0336(15) 0.0284(15) 0.0386(15) -0.0050(12) -0.0050(12) -0.0084(12) C43 0.0503(18) 0.0294(16) 0.0465(17) -0.0033(13) -0.0042(15) -0.0055(13) C44 0.067(2) 0.0299(16) 0.0509(18) -0.0073(13) -0.0055(16) -0.0195(15) C45 0.060(2) 0.0487(19) 0.0525(18) -0.0089(15) -0.0153(16) -0.0285(16) C46 0.0393(16) 0.0374(16) 0.0444(17) -0.0034(13) -0.0135(13) -0.0117(13) O9A 0.0308(10) 0.0500(11) 0.0411(11) -0.0117(9) 0.0012(9) -0.0025(8) N27A 0.0770(19) 0.0477(16) 0.0451(15) 0.0024(12) -0.0082(13) -0.0327(14) C1A 0.0285(14) 0.0349(15) 0.0305(14) -0.0051(11) -0.0018(12) -0.0115(11) C2A 0.0266(14) 0.0252(13) 0.0288(14) -0.0035(11) -0.0038(11) -0.0069(11) C3A 0.0261(13) 0.0264(13) 0.0280(13) -0.0027(11) -0.0049(11) -0.0069(10) C4A 0.0250(14) 0.0267(13) 0.0356(15) -0.0033(11) -0.0004(11) -0.0068(10) C5A 0.0259(14) 0.0255(13) 0.0332(14) -0.0053(11) -0.0037(12) -0.0066(11) C6A 0.0275(14) 0.0248(13) 0.0356(14) -0.0011(11) -0.0047(12) -0.0080(11) C7A 0.0354(15) 0.0386(15) 0.0365(15) 0.0056(13) -0.0127(13) -0.0177(13) C8A 0.0269(14) 0.0294(14) 0.0476(17) 0.0057(13) -0.0104(13) -0.0091(11) C9A 0.0294(14) 0.0237(13) 0.0357(16) -0.0052(11) -0.0022(13) -0.0084(11) C10A 0.0315(15) 0.0252(14) 0.0437(17) -0.0100(12) -0.0097(13) 0.0008(11) C11A 0.0397(18) 0.0489(18) 0.072(2) -0.0160(16) -0.0189(16) -0.0055(14) C12A 0.062(2) 0.075(2) 0.102(3) -0.019(2) -0.047(2) -0.0109(19) C13A 0.105(3) 0.070(2) 0.086(3) -0.010(2) -0.068(3) -0.001(2) C14A 0.099(3) 0.052(2) 0.052(2) 0.0032(16) -0.035(2) -0.0098(19) C15A 0.0531(18) 0.0375(16) 0.0463(18) -0.0006(13) -0.0163(16) -0.0080(14) C21A 0.0248(13) 0.0294(14) 0.0302(14) -0.0040(11) -0.0065(12) -0.0072(11) C22A 0.0328(15) 0.0298(14) 0.0359(15) -0.0065(12) -0.0019(12) -0.0092(11) C23A 0.0359(15) 0.0418(16) 0.0321(15) -0.0021(13) -0.0006(12) -0.0182(13) C24A 0.0353(15) 0.0304(15) 0.0368(15) -0.0002(12) -0.0105(13) -0.0145(12) C25A 0.0435(16) 0.0311(15) 0.0395(16) -0.0066(12) -0.0052(14) -0.0101(12) C26A 0.0360(15) 0.0318(15) 0.0333(15) -0.0027(12) 0.0001(12) -0.0096(12) C27A 0.0469(17) 0.0394(17) 0.0380(16) -0.0025(14) -0.0101(13) -0.0183(14) C30A 0.0278(14) 0.0272(14) 0.0350(14) 0.0001(11) -0.0045(12) -0.0069(11) C31A 0.0278(14) 0.0306(14) 0.0405(16) -0.0021(12) -0.0017(12) -0.0121(12) C32A 0.0407(17) 0.0405(16) 0.0466(18) -0.0026(13) -0.0009(14) -0.0080(13) C33A 0.0478(19) 0.059(2) 0.0506(19) -0.0094(16) 0.0120(16) -0.0151(16) C34A 0.0392(18) 0.0436(19) 0.081(2) -0.0165(17) 0.0119(18) -0.0056(15) C35A 0.0361(18) 0.0401(17) 0.079(2) 0.0027(16) -0.0005(17) -0.0049(14) C36A 0.0285(15) 0.0402(16) 0.0526(18) 0.0011(14) -0.0001(14) -0.0077(13) C41A 0.0354(16) 0.0263(14) 0.0449(17) -0.0013(13) 0.0103(13) -0.0089(12) C42A 0.0413(18) 0.0394(19) 0.110(3) 0.0245(18) -0.0111(19) -0.0109(14) C43A 0.049(2) 0.049(2) 0.155(4) 0.036(3) 0.010(3) 0.0013(18) C44A 0.094(3) 0.035(2) 0.109(4) -0.008(2) 0.048(3) -0.013(2) C45A 0.135(4) 0.056(2) 0.055(2) -0.0176(19) 0.021(2) -0.054(3) C46A 0.084(2) 0.0442(19) 0.0455(18) -0.0061(14) -0.0009(17) -0.0303(17) O9B 0.0346(11) 0.0597(13) 0.0528(12) -0.0106(10) -0.0050(10) -0.0039(9) N27B 0.131(3) 0.082(2) 0.074(2) -0.0353(17) 0.0409(19) -0.077(2) C1B 0.0316(14) 0.0359(15) 0.0310(14) -0.0048(12) -0.0027(12) -0.0099(12) C2B 0.0291(14) 0.0289(14) 0.0326(15) -0.0006(11) -0.0083(12) -0.0087(11) C3B 0.0318(14) 0.0270(13) 0.0312(14) -0.0013(11) -0.0069(12) -0.0087(11) C4B 0.0261(14) 0.0327(14) 0.0372(15) -0.0056(12) -0.0075(12) -0.0061(11) C5B 0.0334(15) 0.0314(14) 0.0284(14) -0.0047(11) -0.0100(12) -0.0077(12) C6B 0.0338(15) 0.0292(14) 0.0333(14) -0.0038(11) -0.0077(12) -0.0107(11) C7B 0.0412(16) 0.0441(16) 0.0294(15) 0.0002(13) -0.0099(13) -0.0136(13) C8B 0.0377(16) 0.0343(15) 0.0383(16) 0.0013(12) -0.0146(13) -0.0089(12) C9B 0.0322(16) 0.0256(14) 0.0481(17) -0.0059(12) -0.0076(14) -0.0084(11) C10B 0.0358(16) 0.0261(14) 0.0462(17) -0.0018(12) -0.0142(14) -0.0013(12) C11B 0.0452(17) 0.0305(15) 0.0493(18) -0.0009(13) -0.0160(15) -0.0054(13) C12B 0.062(2) 0.0321(16) 0.050(2) 0.0003(14) -0.0111(16) -0.0010(14) C13B 0.076(2) 0.053(2) 0.053(2) 0.0070(16) -0.037(2) 0.0018(17) C14B 0.058(2) 0.076(2) 0.074(3) 0.0116(19) -0.039(2) -0.0116(18) C15B 0.0438(18) 0.0477(18) 0.064(2) 0.0067(15) -0.0259(16) -0.0061(14) C21B 0.0302(14) 0.0306(14) 0.0291(14) -0.0002(11) -0.0108(12) -0.0076(11) C22B 0.0431(17) 0.0329(15) 0.0406(16) -0.0081(12) -0.0030(14) -0.0106(13) C23B 0.0460(17) 0.0426(17) 0.0455(17) -0.0044(14) 0.0011(14) -0.0233(14) C24B 0.0553(18) 0.0374(16) 0.0365(16) -0.0026(13) -0.0043(14) -0.0247(14) C25B 0.0508(18) 0.0363(16) 0.0414(16) -0.0099(13) -0.0064(14) -0.0159(13) C26B 0.0320(15) 0.0358(15) 0.0389(16) -0.0045(12) -0.0049(12) -0.0113(12) C27B 0.082(2) 0.057(2) 0.0433(18) -0.0144(15) 0.0162(17) -0.0425(19) C30B 0.0348(15) 0.0412(16) 0.0271(14) -0.0045(12) -0.0063(12) -0.0167(12) C31B 0.0309(15) 0.0538(18) 0.0370(16) -0.0141(14) -0.0031(13) -0.0185(13) C32B 0.0319(16) 0.0586(19) 0.0495(18) -0.0115(16) -0.0019(14) -0.0076(14) C33B 0.0386(19) 0.073(2) 0.067(2) -0.0103(18) -0.0044(17) -0.0055(16) C34B 0.047(2) 0.086(3) 0.070(2) -0.021(2) -0.010(2) -0.0021(18) C35B 0.038(2) 0.115(3) 0.051(2) -0.028(2) 0.0104(16) -0.017(2) C36B 0.0428(19) 0.083(2) 0.0441(18) -0.0111(16) -0.0021(15) -0.0208(17) C41B 0.0428(16) 0.0436(16) 0.0262(14) -0.0033(12) -0.0032(13) -0.0223(14) C42B 0.0555(19) 0.0580(19) 0.0318(15) -0.0026(13) -0.0062(14) -0.0328(15) C43B 0.080(2) 0.071(2) 0.0336(17) -0.0080(16) -0.0052(17) -0.050(2) C44B 0.099(3) 0.053(2) 0.0398(18) -0.0104(16) 0.0039(19) -0.045(2) C45B 0.073(2) 0.0459(19) 0.0412(18) -0.0025(14) 0.0009(16) -0.0233(16) C46B 0.0534(18) 0.0436(18) 0.0352(16) -0.0058(13) -0.0029(14) -0.0228(15) _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 O9 C9 1.217(3) . ? N27 C27 1.148(3) . ? C1 C8 1.473(3) . ? C1 C2 1.516(3) . ? C1 C6 1.535(3) . ? C1 H1 1.0000 . ? C2 C9 1.495(3) . ? C2 C3 1.525(3) . ? C2 C6 1.536(3) . ? C3 C21 1.512(3) . ? C3 C4 1.576(3) . ? C3 H3 1.0000 . ? C4 C7 1.504(3) . ? C4 C5 1.531(3) . ? C4 H4 1.0000 . ? C5 C30 1.341(3) . ? C5 C6 1.477(3) . ? C6 H6 1.0000 . ? C7 C8 1.323(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.501(4) . ? C10 C15 1.379(4) . ? C10 C11 1.401(4) . ? C11 C12 1.411(5) . ? C11 H11 0.9500 . ? C12 C13 1.370(5) . ? C12 H12 0.9500 . ? C13 C14 1.358(4) . ? C13 H13 0.9500 . ? C14 C15 1.390(4) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C21 C26 1.387(3) . ? C21 C22 1.389(3) . ? C22 C23 1.381(3) . ? C22 H22 0.9500 . ? C23 C24 1.383(4) . ? C23 H23 0.9500 . ? C24 C25 1.390(3) . ? C24 C27 1.442(4) . ? C25 C26 1.381(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C30 C31 1.497(3) . ? C30 C41 1.497(3) . ? C31 C36 1.385(3) . ? C31 C32 1.394(3) . ? C32 C33 1.381(3) . ? C32 H32 0.9500 . ? C33 C34 1.374(4) . ? C33 H33 0.9500 . ? C34 C35 1.372(4) . ? C34 H34 0.9500 . ? C35 C36 1.382(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C42 1.390(3) . ? C41 C46 1.391(3) . ? C42 C43 1.382(3) . ? C42 H42 0.9500 . ? C43 C44 1.376(4) . ? C43 H43 0.9500 . ? C44 C45 1.378(4) . ? C44 H44 0.9500 . ? C45 C46 1.379(3) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? O9A C9A 1.220(3) . ? N27A C27A 1.147(3) . ? C1A C7A 1.478(3) . ? C1A C2A 1.517(3) . ? C1A C6A 1.543(3) . ? C1A H1A 1.0000 . ? C2A C9A 1.494(3) . ? C2A C3A 1.520(3) . ? C2A C6A 1.533(3) . ? C3A C21A 1.518(3) . ? C3A C4A 1.573(3) . ? C3A H3A 1.0000 . ? C4A C8A 1.502(3) . ? C4A C5A 1.524(3) . ? C4A H4A 1.0000 . ? C5A C30A 1.339(3) . ? C5A C6A 1.478(3) . ? C6A H6A 1.0000 . ? C7A C8A 1.325(3) . ? C7A H7A 0.9500 . ? C8A H8A 0.9500 . ? C9A C10A 1.480(3) . ? C10A C15A 1.386(3) . ? C10A C11A 1.394(4) . ? C11A C12A 1.378(4) . ? C11A H11A 0.9500 . ? C12A C13A 1.378(5) . ? C12A H12A 0.9500 . ? C13A C14A 1.370(5) . ? C13A H13A 0.9500 . ? C14A C15A 1.380(4) . ? C14A H14A 0.9500 . ? C15A H15A 0.9500 . ? C21A C22A 1.387(3) . ? C21A C26A 1.391(3) . ? C22A C23A 1.385(3) . ? C22A H22A 0.9500 . ? C23A C24A 1.379(3) . ? C23A H23A 0.9500 . ? C24A C25A 1.386(3) . ? C24A C27A 1.445(3) . ? C25A C26A 1.384(3) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? C30A C31A 1.488(3) . ? C30A C41A 1.497(3) . ? C31A C36A 1.389(3) . ? C31A C32A 1.394(3) . ? C32A C33A 1.382(4) . ? C32A H32A 0.9500 . ? C33A C34A 1.379(4) . ? C33A H33A 0.9500 . ? C34A C35A 1.368(4) . ? C34A H34A 0.9500 . ? C35A C36A 1.379(4) . ? C35A H35A 0.9500 . ? C36A H36A 0.9500 . ? C41A C46A 1.381(4) . ? C41A C42A 1.388(4) . ? C42A C43A 1.397(5) . ? C42A H42A 0.9500 . ? C43A C44A 1.362(6) . ? C43A H43A 0.9500 . ? C44A C45A 1.371(6) . ? C44A H44A 0.9500 . ? C45A C46A 1.394(4) . ? C45A H45A 0.9500 . ? C46A H46A 0.9500 . ? O9B C9B 1.222(3) . ? N27B C27B 1.147(3) . ? C1B C7B 1.475(3) . ? C1B C2B 1.510(3) . ? C1B C6B 1.535(3) . ? C1B H1B 1.0000 . ? C2B C9B 1.496(3) . ? C2B C3B 1.528(3) . ? C2B C6B 1.536(3) . ? C3B C21B 1.507(3) . ? C3B C4B 1.567(3) . ? C3B H3B 1.0000 . ? C4B C8B 1.503(3) . ? C4B C5B 1.523(3) . ? C4B H4B 1.0000 . ? C5B C30B 1.346(3) . ? C5B C6B 1.489(3) . ? C6B H6B 1.0000 . ? C7B C8B 1.321(3) . ? C7B H7B 0.9500 . ? C8B H8B 0.9500 . ? C9B C10B 1.482(4) . ? C10B C11B 1.389(3) . ? C10B C15B 1.398(4) . ? C11B C12B 1.392(4) . ? C11B H11B 0.9500 . ? C12B C13B 1.387(4) . ? C12B H12B 0.9500 . ? C13B C14B 1.372(4) . ? C13B H13B 0.9500 . ? C14B C15B 1.366(4) . ? C14B H14B 0.9500 . ? C15B H15B 0.9500 . ? C21B C22B 1.387(3) . ? C21B C26B 1.390(3) . ? C22B C23B 1.385(3) . ? C22B H22B 0.9500 . ? C23B C24B 1.384(4) . ? C23B H23B 0.9500 . ? C24B C25B 1.389(4) . ? C24B C27B 1.441(4) . ? C25B C26B 1.376(3) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? C30B C41B 1.485(3) . ? C30B C31B 1.502(3) . ? C31B C32B 1.387(4) . ? C31B C36B 1.390(4) . ? C32B C33B 1.379(4) . ? C32B H32B 0.9500 . ? C33B C34B 1.362(4) . ? C33B H33B 0.9500 . ? C34B C35B 1.370(4) . ? C34B H34B 0.9500 . ? C35B C36B 1.404(4) . ? C35B H35B 0.9500 . ? C36B H36B 0.9500 . ? C41B C46B 1.390(4) . ? C41B C42B 1.399(4) . ? C42B C43B 1.381(4) . ? C42B H42B 0.9500 . ? C43B C44B 1.375(4) . ? C43B H43B 0.9500 . ? C44B C45B 1.385(4) . ? C44B H44B 0.9500 . ? C45B C46B 1.389(4) . ? C45B H45B 0.9500 . ? C46B H46B 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 C8 C1 C2 118.0(2) . . ? C8 C1 C6 116.6(2) . . ? C2 C1 C6 60.47(15) . . ? C8 C1 H1 116.6 . . ? C2 C1 H1 116.6 . . ? C6 C1 H1 116.6 . . ? C9 C2 C1 120.2(2) . . ? C9 C2 C3 119.1(2) . . ? C1 C2 C3 114.6(2) . . ? C9 C2 C6 121.65(19) . . ? C1 C2 C6 60.38(15) . . ? C3 C2 C6 106.84(18) . . ? C21 C3 C2 115.71(19) . . ? C21 C3 C4 114.13(18) . . ? C2 C3 C4 101.53(18) . . ? C21 C3 H3 108.4 . . ? C2 C3 H3 108.4 . . ? C4 C3 H3 108.4 . . ? C7 C4 C5 105.56(19) . . ? C7 C4 C3 107.95(18) . . ? C5 C4 C3 102.13(17) . . ? C7 C4 H4 113.4 . . ? C5 C4 H4 113.4 . . ? C3 C4 H4 113.4 . . ? C30 C5 C6 127.0(2) . . ? C30 C5 C4 127.9(2) . . ? C6 C5 C4 104.98(18) . . ? C5 C6 C1 112.7(2) . . ? C5 C6 C2 107.22(19) . . ? C1 C6 C2 59.15(15) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? C2 C6 H6 120.7 . . ? C8 C7 C4 115.5(2) . . ? C8 C7 H7 122.2 . . ? C4 C7 H7 122.2 . . ? C7 C8 C1 117.6(2) . . ? C7 C8 H8 121.2 . . ? C1 C8 H8 121.2 . . ? O9 C9 C2 121.8(3) . . ? O9 C9 C10 121.6(2) . . ? C2 C9 C10 116.6(2) . . ? C15 C10 C11 118.8(3) . . ? C15 C10 C9 121.4(2) . . ? C11 C10 C9 119.7(3) . . ? C10 C11 C12 118.7(3) . . ? C10 C11 H11 120.7 . . ? C12 C11 H11 120.7 . . ? C13 C12 C11 120.4(3) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 121.2(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 119.1(3) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C10 C15 C14 121.8(3) . . ? C10 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C26 C21 C22 118.1(2) . . ? C26 C21 C3 119.9(2) . . ? C22 C21 C3 121.9(2) . . ? C23 C22 C21 121.2(2) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 119.9(2) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? C23 C24 C25 119.8(2) . . ? C23 C24 C27 118.6(2) . . ? C25 C24 C27 121.6(2) . . ? C26 C25 C24 119.6(2) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C21 121.4(2) . . ? C25 C26 H26 119.3 . . ? C21 C26 H26 119.3 . . ? N27 C27 C24 177.6(3) . . ? C5 C30 C31 122.5(2) . . ? C5 C30 C41 121.3(2) . . ? C31 C30 C41 116.09(19) . . ? C36 C31 C32 117.8(2) . . ? C36 C31 C30 122.4(2) . . ? C32 C31 C30 119.8(2) . . ? C33 C32 C31 120.6(2) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C34 C33 C32 120.6(3) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C35 C34 C33 119.6(3) . . ? C35 C34 H34 120.2 . . ? C33 C34 H34 120.2 . . ? C34 C35 C36 120.1(3) . . ? C34 C35 H35 120.0 . . ? C36 C35 H35 120.0 . . ? C35 C36 C31 121.3(3) . . ? C35 C36 H36 119.3 . . ? C31 C36 H36 119.3 . . ? C42 C41 C46 117.8(2) . . ? C42 C41 C30 122.9(2) . . ? C46 C41 C30 119.2(2) . . ? C43 C42 C41 120.6(2) . . ? C43 C42 H42 119.7 . . ? C41 C42 H42 119.7 . . ? C44 C43 C42 120.7(3) . . ? C44 C43 H43 119.7 . . ? C42 C43 H43 119.7 . . ? C43 C44 C45 119.5(2) . . ? C43 C44 H44 120.3 . . ? C45 C44 H44 120.3 . . ? C44 C45 C46 120.0(3) . . ? C44 C45 H45 120.0 . . ? C46 C45 H45 120.0 . . ? C45 C46 C41 121.4(2) . . ? C45 C46 H46 119.3 . . ? C41 C46 H46 119.3 . . ? C7A C1A C2A 118.1(2) . . ? C7A C1A C6A 117.3(2) . . ? C2A C1A C6A 60.15(15) . . ? C7A C1A H1A 116.5 . . ? C2A C1A H1A 116.5 . . ? C6A C1A H1A 116.5 . . ? C9A C2A C1A 118.9(2) . . ? C9A C2A C3A 120.6(2) . . ? C1A C2A C3A 114.00(19) . . ? C9A C2A C6A 121.51(19) . . ? C1A C2A C6A 60.79(15) . . ? C3A C2A C6A 106.46(18) . . ? C21A C3A C2A 115.36(18) . . ? C21A C3A C4A 114.14(18) . . ? C2A C3A C4A 101.95(18) . . ? C21A C3A H3A 108.3 . . ? C2A C3A H3A 108.3 . . ? C4A C3A H3A 108.3 . . ? C8A C4A C5A 107.46(19) . . ? C8A C4A C3A 107.86(18) . . ? C5A C4A C3A 101.15(17) . . ? C8A C4A H4A 113.2 . . ? C5A C4A H4A 113.2 . . ? C3A C4A H4A 113.2 . . ? C30A C5A C6A 127.0(2) . . ? C30A C5A C4A 128.1(2) . . ? C6A C5A C4A 104.99(18) . . ? C5A C6A C2A 106.83(19) . . ? C5A C6A C1A 113.07(19) . . ? C2A C6A C1A 59.06(14) . . ? C5A C6A H6A 120.7 . . ? C2A C6A H6A 120.7 . . ? C1A C6A H6A 120.7 . . ? C8A C7A C1A 117.3(2) . . ? C8A C7A H7A 121.4 . . ? C1A C7A H7A 121.4 . . ? C7A C8A C4A 115.4(2) . . ? C7A C8A H8A 122.3 . . ? C4A C8A H8A 122.3 . . ? O9A C9A C10A 120.4(2) . . ? O9A C9A C2A 121.0(2) . . ? C10A C9A C2A 118.6(2) . . ? C15A C10A C11A 118.9(3) . . ? C15A C10A C9A 121.6(2) . . ? C11A C10A C9A 119.5(2) . . ? C12A C11A C10A 120.7(3) . . ? C12A C11A H11A 119.6 . . ? C10A C11A H11A 119.6 . . ? C11A C12A C13A 119.2(3) . . ? C11A C12A H12A 120.4 . . ? C13A C12A H12A 120.4 . . ? C14A C13A C12A 121.0(3) . . ? C14A C13A H13A 119.5 . . ? C12A C13A H13A 119.5 . . ? C13A C14A C15A 119.8(3) . . ? C13A C14A H14A 120.1 . . ? C15A C14A H14A 120.1 . . ? C14A C15A C10A 120.4(3) . . ? C14A C15A H15A 119.8 . . ? C10A C15A H15A 119.8 . . ? C22A C21A C26A 118.0(2) . . ? C22A C21A C3A 122.0(2) . . ? C26A C21A C3A 120.0(2) . . ? C23A C22A C21A 120.8(2) . . ? C23A C22A H22A 119.6 . . ? C21A C22A H22A 119.6 . . ? C24A C23A C22A 120.4(2) . . ? C24A C23A H23A 119.8 . . ? C22A C23A H23A 119.8 . . ? C23A C24A C25A 119.8(2) . . ? C23A C24A C27A 118.8(2) . . ? C25A C24A C27A 121.3(2) . . ? C26A C25A C24A 119.3(2) . . ? C26A C25A H25A 120.4 . . ? C24A C25A H25A 120.4 . . ? C25A C26A C21A 121.7(2) . . ? C25A C26A H26A 119.2 . . ? C21A C26A H26A 119.2 . . ? N27A C27A C24A 177.5(3) . . ? C5A C30A C31A 123.4(2) . . ? C5A C30A C41A 120.5(2) . . ? C31A C30A C41A 116.1(2) . . ? C36A C31A C32A 118.0(2) . . ? C36A C31A C30A 121.7(2) . . ? C32A C31A C30A 120.3(2) . . ? C33A C32A C31A 120.5(3) . . ? C33A C32A H32A 119.8 . . ? C31A C32A H32A 119.8 . . ? C34A C33A C32A 120.3(3) . . ? C34A C33A H33A 119.8 . . ? C32A C33A H33A 119.8 . . ? C35A C34A C33A 119.9(3) . . ? C35A C34A H34A 120.1 . . ? C33A C34A H34A 120.1 . . ? C34A C35A C36A 120.1(3) . . ? C34A C35A H35A 119.9 . . ? C36A C35A H35A 119.9 . . ? C35A C36A C31A 121.2(3) . . ? C35A C36A H36A 119.4 . . ? C31A C36A H36A 119.4 . . ? C46A C41A C42A 118.8(3) . . ? C46A C41A C30A 120.3(3) . . ? C42A C41A C30A 120.9(3) . . ? C41A C42A C43A 119.9(4) . . ? C41A C42A H42A 120.0 . . ? C43A C42A H42A 120.0 . . ? C44A C43A C42A 120.2(4) . . ? C44A C43A H43A 119.9 . . ? C42A C43A H43A 119.9 . . ? C43A C44A C45A 120.9(4) . . ? C43A C44A H44A 119.6 . . ? C45A C44A H44A 119.6 . . ? C44A C45A C46A 119.2(4) . . ? C44A C45A H45A 120.4 . . ? C46A C45A H45A 120.4 . . ? C41A C46A C45A 121.0(3) . . ? C41A C46A H46A 119.5 . . ? C45A C46A H46A 119.5 . . ? C7B C1B C2B 118.5(2) . . ? C7B C1B C6B 118.4(2) . . ? C2B C1B C6B 60.59(15) . . ? C7B C1B H1B 116.0 . . ? C2B C1B H1B 116.0 . . ? C6B C1B H1B 116.0 . . ? C9B C2B C1B 118.5(2) . . ? C9B C2B C3B 121.5(2) . . ? C1B C2B C3B 113.89(19) . . ? C9B C2B C6B 121.3(2) . . ? C1B C2B C6B 60.53(15) . . ? C3B C2B C6B 105.74(18) . . ? C21B C3B C2B 116.85(19) . . ? C21B C3B C4B 113.40(18) . . ? C2B C3B C4B 101.89(18) . . ? C21B C3B H3B 108.1 . . ? C2B C3B H3B 108.1 . . ? C4B C3B H3B 108.1 . . ? C8B C4B C5B 108.41(19) . . ? C8B C4B C3B 107.78(19) . . ? C5B C4B C3B 101.28(18) . . ? C8B C4B H4B 112.9 . . ? C5B C4B H4B 112.9 . . ? C3B C4B H4B 112.9 . . ? C30B C5B C6B 130.2(2) . . ? C30B C5B C4B 125.5(2) . . ? C6B C5B C4B 104.30(19) . . ? C5B C6B C1B 112.8(2) . . ? C5B C6B C2B 107.11(19) . . ? C1B C6B C2B 58.88(15) . . ? C5B C6B H6B 120.7 . . ? C1B C6B H6B 120.7 . . ? C2B C6B H6B 120.7 . . ? C8B C7B C1B 116.7(2) . . ? C8B C7B H7B 121.7 . . ? C1B C7B H7B 121.7 . . ? C7B C8B C4B 115.6(2) . . ? C7B C8B H8B 122.2 . . ? C4B C8B H8B 122.2 . . ? O9B C9B C10B 120.5(2) . . ? O9B C9B C2B 121.0(2) . . ? C10B C9B C2B 118.4(2) . . ? C11B C10B C15B 118.8(3) . . ? C11B C10B C9B 122.4(2) . . ? C15B C10B C9B 118.8(2) . . ? C10B C11B C12B 120.5(3) . . ? C10B C11B H11B 119.7 . . ? C12B C11B H11B 119.7 . . ? C13B C12B C11B 119.1(3) . . ? C13B C12B H12B 120.5 . . ? C11B C12B H12B 120.5 . . ? C14B C13B C12B 120.6(3) . . ? C14B C13B H13B 119.7 . . ? C12B C13B H13B 119.7 . . ? C15B C14B C13B 120.5(3) . . ? C15B C14B H14B 119.8 . . ? C13B C14B H14B 119.8 . . ? C14B C15B C10B 120.5(3) . . ? C14B C15B H15B 119.7 . . ? C10B C15B H15B 119.7 . . ? C22B C21B C26B 118.4(2) . . ? C22B C21B C3B 122.5(2) . . ? C26B C21B C3B 119.1(2) . . ? C23B C22B C21B 121.0(2) . . ? C23B C22B H22B 119.5 . . ? C21B C22B H22B 119.5 . . ? C24B C23B C22B 119.7(2) . . ? C24B C23B H23B 120.1 . . ? C22B C23B H23B 120.1 . . ? C23B C24B C25B 119.9(2) . . ? C23B C24B C27B 120.1(2) . . ? C25B C24B C27B 119.9(2) . . ? C26B C25B C24B 119.7(2) . . ? C26B C25B H25B 120.1 . . ? C24B C25B H25B 120.1 . . ? C25B C26B C21B 121.3(2) . . ? C25B C26B H26B 119.4 . . ? C21B C26B H26B 119.4 . . ? N27B C27B C24B 177.5(3) . . ? C5B C30B C41B 124.4(2) . . ? C5B C30B C31B 119.3(2) . . ? C41B C30B C31B 116.3(2) . . ? C32B C31B C36B 117.6(3) . . ? C32B C31B C30B 120.5(2) . . ? C36B C31B C30B 121.9(3) . . ? C33B C32B C31B 122.2(3) . . ? C33B C32B H32B 118.9 . . ? C31B C32B H32B 118.9 . . ? C34B C33B C32B 119.5(3) . . ? C34B C33B H33B 120.3 . . ? C32B C33B H33B 120.3 . . ? C33B C34B C35B 120.4(3) . . ? C33B C34B H34B 119.8 . . ? C35B C34B H34B 119.8 . . ? C34B C35B C36B 120.4(3) . . ? C34B C35B H35B 119.8 . . ? C36B C35B H35B 119.8 . . ? C31B C36B C35B 119.9(3) . . ? C31B C36B H36B 120.0 . . ? C35B C36B H36B 120.0 . . ? C46B C41B C42B 117.7(2) . . ? C46B C41B C30B 122.5(2) . . ? C42B C41B C30B 119.8(2) . . ? C43B C42B C41B 121.1(3) . . ? C43B C42B H42B 119.4 . . ? C41B C42B H42B 119.4 . . ? C44B C43B C42B 120.3(3) . . ? C44B C43B H43B 119.8 . . ? C42B C43B H43B 119.8 . . ? C43B C44B C45B 119.7(3) . . ? C43B C44B H44B 120.1 . . ? C45B C44B H44B 120.1 . . ? C44B C45B C46B 119.9(3) . . ? C44B C45B H45B 120.0 . . ? C46B C45B H45B 120.0 . . ? C45B C46B C41B 121.2(3) . . ? C45B C46B H46B 119.4 . . ? C41B C46B H46B 119.4 . . ? 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 C8 C1 C2 C9 142.0(2) . . . . ? C6 C1 C2 C9 -111.6(2) . . . . ? C8 C1 C2 C3 -10.3(3) . . . . ? C6 C1 C2 C3 96.1(2) . . . . ? C8 C1 C2 C6 -106.4(2) . . . . ? C9 C2 C3 C21 -66.8(3) . . . . ? C1 C2 C3 C21 85.8(2) . . . . ? C6 C2 C3 C21 150.4(2) . . . . ? C9 C2 C3 C4 169.0(2) . . . . ? C1 C2 C3 C4 -38.3(2) . . . . ? C6 C2 C3 C4 26.3(2) . . . . ? C21 C3 C4 C7 -54.0(3) . . . . ? C2 C3 C4 C7 71.2(2) . . . . ? C21 C3 C4 C5 -165.01(19) . . . . ? C2 C3 C4 C5 -39.8(2) . . . . ? C7 C4 C5 C30 102.0(3) . . . . ? C3 C4 C5 C30 -145.2(2) . . . . ? C7 C4 C5 C6 -73.5(2) . . . . ? C3 C4 C5 C6 39.3(2) . . . . ? C30 C5 C6 C1 -135.6(2) . . . . ? C4 C5 C6 C1 39.9(2) . . . . ? C30 C5 C6 C2 161.3(2) . . . . ? C4 C5 C6 C2 -23.2(2) . . . . ? C8 C1 C6 C5 11.5(3) . . . . ? C2 C1 C6 C5 -97.1(2) . . . . ? C8 C1 C6 C2 108.6(2) . . . . ? C9 C2 C6 C5 -144.3(2) . . . . ? C1 C2 C6 C5 106.5(2) . . . . ? C3 C2 C6 C5 -2.7(2) . . . . ? C9 C2 C6 C1 109.2(3) . . . . ? C3 C2 C6 C1 -109.2(2) . . . . ? C5 C4 C7 C8 54.2(3) . . . . ? C3 C4 C7 C8 -54.5(3) . . . . ? C4 C7 C8 C1 0.2(3) . . . . ? C2 C1 C8 C7 34.0(3) . . . . ? C6 C1 C8 C7 -35.1(3) . . . . ? C1 C2 C9 O9 -15.0(3) . . . . ? C3 C2 C9 O9 136.1(2) . . . . ? C6 C2 C9 O9 -86.7(3) . . . . ? C1 C2 C9 C10 166.0(2) . . . . ? C3 C2 C9 C10 -42.9(3) . . . . ? C6 C2 C9 C10 94.3(3) . . . . ? O9 C9 C10 C15 139.9(3) . . . . ? C2 C9 C10 C15 -41.1(3) . . . . ? O9 C9 C10 C11 -40.2(4) . . . . ? C2 C9 C10 C11 138.8(2) . . . . ? C15 C10 C11 C12 1.7(4) . . . . ? C9 C10 C11 C12 -178.2(2) . . . . ? C10 C11 C12 C13 -2.5(4) . . . . ? C11 C12 C13 C14 1.0(5) . . . . ? C12 C13 C14 C15 1.1(5) . . . . ? C11 C10 C15 C14 0.4(4) . . . . ? C9 C10 C15 C14 -179.7(2) . . . . ? C13 C14 C15 C10 -1.9(4) . . . . ? C2 C3 C21 C26 161.9(2) . . . . ? C4 C3 C21 C26 -80.8(3) . . . . ? C2 C3 C21 C22 -21.8(3) . . . . ? C4 C3 C21 C22 95.5(3) . . . . ? C26 C21 C22 C23 3.6(4) . . . . ? C3 C21 C22 C23 -172.9(2) . . . . ? C21 C22 C23 C24 -1.7(4) . . . . ? C22 C23 C24 C25 -1.2(4) . . . . ? C22 C23 C24 C27 176.7(2) . . . . ? C23 C24 C25 C26 2.1(4) . . . . ? C27 C24 C25 C26 -175.7(2) . . . . ? C24 C25 C26 C21 -0.1(4) . . . . ? C22 C21 C26 C25 -2.7(4) . . . . ? C3 C21 C26 C25 173.8(2) . . . . ? C23 C24 C27 N27 -21(8) . . . . ? C25 C24 C27 N27 157(8) . . . . ? C6 C5 C30 C31 174.4(2) . . . . ? C4 C5 C30 C31 -0.1(4) . . . . ? C6 C5 C30 C41 -1.4(4) . . . . ? C4 C5 C30 C41 -176.0(2) . . . . ? C5 C30 C31 C36 -44.6(3) . . . . ? C41 C30 C31 C36 131.5(2) . . . . ? C5 C30 C31 C32 136.2(2) . . . . ? C41 C30 C31 C32 -47.7(3) . . . . ? C36 C31 C32 C33 2.9(4) . . . . ? C30 C31 C32 C33 -177.8(2) . . . . ? C31 C32 C33 C34 -1.9(4) . . . . ? C32 C33 C34 C35 -0.2(4) . . . . ? C33 C34 C35 C36 1.2(4) . . . . ? C34 C35 C36 C31 -0.1(4) . . . . ? C32 C31 C36 C35 -1.9(4) . . . . ? C30 C31 C36 C35 178.8(2) . . . . ? C5 C30 C41 C42 -58.1(3) . . . . ? C31 C30 C41 C42 125.8(2) . . . . ? C5 C30 C41 C46 120.3(3) . . . . ? C31 C30 C41 C46 -55.8(3) . . . . ? C46 C41 C42 C43 0.4(4) . . . . ? C30 C41 C42 C43 178.8(2) . . . . ? C41 C42 C43 C44 -0.9(4) . . . . ? C42 C43 C44 C45 0.5(4) . . . . ? C43 C44 C45 C46 0.5(4) . . . . ? C44 C45 C46 C41 -1.1(4) . . . . ? C42 C41 C46 C45 0.6(4) . . . . ? C30 C41 C46 C45 -177.9(2) . . . . ? C7A C1A C2A C9A -140.9(2) . . . . ? C6A C1A C2A C9A 112.0(2) . . . . ? C7A C1A C2A C3A 10.9(3) . . . . ? C6A C1A C2A C3A -96.1(2) . . . . ? C7A C1A C2A C6A 107.1(2) . . . . ? C9A C2A C3A C21A 65.6(3) . . . . ? C1A C2A C3A C21A -85.8(2) . . . . ? C6A C2A C3A C21A -150.59(19) . . . . ? C9A C2A C3A C4A -170.2(2) . . . . ? C1A C2A C3A C4A 38.5(2) . . . . ? C6A C2A C3A C4A -26.3(2) . . . . ? C21A C3A C4A C8A 53.3(3) . . . . ? C2A C3A C4A C8A -71.7(2) . . . . ? C21A C3A C4A C5A 165.96(19) . . . . ? C2A C3A C4A C5A 40.9(2) . . . . ? C8A C4A C5A C30A -108.2(3) . . . . ? C3A C4A C5A C30A 138.9(3) . . . . ? C8A C4A C5A C6A 71.9(2) . . . . ? C3A C4A C5A C6A -41.0(2) . . . . ? C30A C5A C6A C2A -154.8(2) . . . . ? C4A C5A C6A C2A 25.2(2) . . . . ? C30A C5A C6A C1A 142.3(2) . . . . ? C4A C5A C6A C1A -37.8(2) . . . . ? C9A C2A C6A C5A 144.9(2) . . . . ? C1A C2A C6A C5A -107.2(2) . . . . ? C3A C2A C6A C5A 1.5(2) . . . . ? C9A C2A C6A C1A -107.9(2) . . . . ? C3A C2A C6A C1A 108.7(2) . . . . ? C7A C1A C6A C5A -11.9(3) . . . . ? C2A C1A C6A C5A 96.4(2) . . . . ? C7A C1A C6A C2A -108.3(2) . . . . ? C2A C1A C7A C8A -35.3(3) . . . . ? C6A C1A C7A C8A 33.6(3) . . . . ? C1A C7A C8A C4A 1.0(3) . . . . ? C5A C4A C8A C7A -54.5(3) . . . . ? C3A C4A C8A C7A 53.8(3) . . . . ? C1A C2A C9A O9A 17.9(3) . . . . ? C3A C2A C9A O9A -132.1(2) . . . . ? C6A C2A C9A O9A 89.5(3) . . . . ? C1A C2A C9A C10A -163.3(2) . . . . ? C3A C2A C9A C10A 46.7(3) . . . . ? C6A C2A C9A C10A -91.7(3) . . . . ? O9A C9A C10A C15A -140.1(2) . . . . ? C2A C9A C10A C15A 41.1(3) . . . . ? O9A C9A C10A C11A 38.1(3) . . . . ? C2A C9A C10A C11A -140.6(2) . . . . ? C15A C10A C11A C12A -1.1(4) . . . . ? C9A C10A C11A C12A -179.4(2) . . . . ? C10A C11A C12A C13A 2.1(5) . . . . ? C11A C12A C13A C14A -1.2(5) . . . . ? C12A C13A C14A C15A -0.7(5) . . . . ? C13A C14A C15A C10A 1.7(4) . . . . ? C11A C10A C15A C14A -0.8(4) . . . . ? C9A C10A C15A C14A 177.5(2) . . . . ? C2A C3A C21A C22A 4.0(3) . . . . ? C4A C3A C21A C22A -113.6(2) . . . . ? C2A C3A C21A C26A -177.1(2) . . . . ? C4A C3A C21A C26A 65.3(3) . . . . ? C26A C21A C22A C23A -2.3(4) . . . . ? C3A C21A C22A C23A 176.6(2) . . . . ? C21A C22A C23A C24A -0.5(4) . . . . ? C22A C23A C24A C25A 2.5(4) . . . . ? C22A C23A C24A C27A -174.4(2) . . . . ? C23A C24A C25A C26A -1.8(4) . . . . ? C27A C24A C25A C26A 175.1(2) . . . . ? C24A C25A C26A C21A -1.0(4) . . . . ? C22A C21A C26A C25A 3.0(4) . . . . ? C3A C21A C26A C25A -175.9(2) . . . . ? C23A C24A C27A N27A 51(7) . . . . ? C25A C24A C27A N27A -126(7) . . . . ? C6A C5A C30A C31A -175.0(2) . . . . ? C4A C5A C30A C31A 5.1(4) . . . . ? C6A C5A C30A C41A 3.3(4) . . . . ? C4A C5A C30A C41A -176.6(2) . . . . ? C5A C30A C31A C36A 46.3(4) . . . . ? C41A C30A C31A C36A -132.0(3) . . . . ? C5A C30A C31A C32A -135.8(3) . . . . ? C41A C30A C31A C32A 45.9(3) . . . . ? C36A C31A C32A C33A -1.8(4) . . . . ? C30A C31A C32A C33A -179.7(2) . . . . ? C31A C32A C33A C34A 1.6(4) . . . . ? C32A C33A C34A C35A -0.7(5) . . . . ? C33A C34A C35A C36A 0.0(5) . . . . ? C34A C35A C36A C31A -0.2(4) . . . . ? C32A C31A C36A C35A 1.1(4) . . . . ? C30A C31A C36A C35A 179.0(2) . . . . ? C5A C30A C41A C46A -107.3(3) . . . . ? C31A C30A C41A C46A 71.1(3) . . . . ? C5A C30A C41A C42A 73.0(3) . . . . ? C31A C30A C41A C42A -108.6(3) . . . . ? C46A C41A C42A C43A 1.0(4) . . . . ? C30A C41A C42A C43A -179.4(3) . . . . ? C41A C42A C43A C44A -0.1(5) . . . . ? C42A C43A C44A C45A 0.1(6) . . . . ? C43A C44A C45A C46A -0.9(6) . . . . ? C42A C41A C46A C45A -1.8(4) . . . . ? C30A C41A C46A C45A 178.6(2) . . . . ? C44A C45A C46A C41A 1.8(5) . . . . ? C7B C1B C2B C9B 139.7(2) . . . . ? C6B C1B C2B C9B -111.9(2) . . . . ? C7B C1B C2B C3B -13.2(3) . . . . ? C6B C1B C2B C3B 95.2(2) . . . . ? C7B C1B C2B C6B -108.4(2) . . . . ? C9B C2B C3B C21B -64.7(3) . . . . ? C1B C2B C3B C21B 87.4(2) . . . . ? C6B C2B C3B C21B 151.6(2) . . . . ? C9B C2B C3B C4B 171.2(2) . . . . ? C1B C2B C3B C4B -36.8(2) . . . . ? C6B C2B C3B C4B 27.5(2) . . . . ? C21B C3B C4B C8B -55.1(3) . . . . ? C2B C3B C4B C8B 71.3(2) . . . . ? C21B C3B C4B C5B -168.85(19) . . . . ? C2B C3B C4B C5B -42.4(2) . . . . ? C8B C4B C5B C30B 108.5(3) . . . . ? C3B C4B C5B C30B -138.3(2) . . . . ? C8B C4B C5B C6B -71.4(2) . . . . ? C3B C4B C5B C6B 41.8(2) . . . . ? C30B C5B C6B C1B -142.2(3) . . . . ? C4B C5B C6B C1B 37.7(2) . . . . ? C30B C5B C6B C2B 155.0(2) . . . . ? C4B C5B C6B C2B -25.1(2) . . . . ? C7B C1B C6B C5B 11.7(3) . . . . ? C2B C1B C6B C5B -96.8(2) . . . . ? C7B C1B C6B C2B 108.5(2) . . . . ? C9B C2B C6B C5B -145.9(2) . . . . ? C1B C2B C6B C5B 106.8(2) . . . . ? C3B C2B C6B C5B -2.1(2) . . . . ? C9B C2B C6B C1B 107.3(3) . . . . ? C3B C2B C6B C1B -108.9(2) . . . . ? C2B C1B C7B C8B 36.2(3) . . . . ? C6B C1B C7B C8B -33.8(3) . . . . ? C1B C7B C8B C4B -0.2(3) . . . . ? C5B C4B C8B C7B 53.9(3) . . . . ? C3B C4B C8B C7B -55.0(3) . . . . ? C1B C2B C9B O9B -15.5(3) . . . . ? C3B C2B C9B O9B 135.3(2) . . . . ? C6B C2B C9B O9B -86.6(3) . . . . ? C1B C2B C9B C10B 165.6(2) . . . . ? C3B C2B C9B C10B -43.6(3) . . . . ? C6B C2B C9B C10B 94.6(3) . . . . ? O9B C9B C10B C11B 148.2(2) . . . . ? C2B C9B C10B C11B -33.0(3) . . . . ? O9B C9B C10B C15B -31.7(3) . . . . ? C2B C9B C10B C15B 147.1(2) . . . . ? C15B C10B C11B C12B 0.4(4) . . . . ? C9B C10B C11B C12B -179.5(2) . . . . ? C10B C11B C12B C13B -1.1(4) . . . . ? C11B C12B C13B C14B 0.8(4) . . . . ? C12B C13B C14B C15B 0.1(5) . . . . ? C13B C14B C15B C10B -0.8(5) . . . . ? C11B C10B C15B C14B 0.6(4) . . . . ? C9B C10B C15B C14B -179.5(3) . . . . ? C2B C3B C21B C22B -5.5(3) . . . . ? C4B C3B C21B C22B 112.6(3) . . . . ? C2B C3B C21B C26B 175.5(2) . . . . ? C4B C3B C21B C26B -66.4(3) . . . . ? C26B C21B C22B C23B 0.5(4) . . . . ? C3B C21B C22B C23B -178.6(2) . . . . ? C21B C22B C23B C24B 0.5(4) . . . . ? C22B C23B C24B C25B -0.3(4) . . . . ? C22B C23B C24B C27B -179.5(3) . . . . ? C23B C24B C25B C26B -0.9(4) . . . . ? C27B C24B C25B C26B 178.3(3) . . . . ? C24B C25B C26B C21B 2.0(4) . . . . ? C22B C21B C26B C25B -1.7(4) . . . . ? C3B C21B C26B C25B 177.3(2) . . . . ? C23B C24B C27B N27B 140(9) . . . . ? C25B C24B C27B N27B -40(9) . . . . ? C6B C5B C30B C41B -7.0(4) . . . . ? C4B C5B C30B C41B 173.2(2) . . . . ? C6B C5B C30B C31B 169.0(2) . . . . ? C4B C5B C30B C31B -10.9(4) . . . . ? C5B C30B C31B C32B -54.4(3) . . . . ? C41B C30B C31B C32B 121.8(3) . . . . ? C5B C30B C31B C36B 127.8(3) . . . . ? C41B C30B C31B C36B -55.9(3) . . . . ? C36B C31B C32B C33B -1.1(4) . . . . ? C30B C31B C32B C33B -178.9(3) . . . . ? C31B C32B C33B C34B 0.4(5) . . . . ? C32B C33B C34B C35B 0.3(5) . . . . ? C33B C34B C35B C36B -0.2(5) . . . . ? C32B C31B C36B C35B 1.1(4) . . . . ? C30B C31B C36B C35B 178.9(3) . . . . ? C34B C35B C36B C31B -0.6(5) . . . . ? C5B C30B C41B C46B -39.1(4) . . . . ? C31B C30B C41B C46B 144.8(2) . . . . ? C5B C30B C41B C42B 142.4(3) . . . . ? C31B C30B C41B C42B -33.6(3) . . . . ? C46B C41B C42B C43B 1.1(4) . . . . ? C30B C41B C42B C43B 179.6(2) . . . . ? C41B C42B C43B C44B 0.1(4) . . . . ? C42B C43B C44B C45B -1.0(4) . . . . ? C43B C44B C45B C46B 0.6(4) . . . . ? C44B C45B C46B C41B 0.7(4) . . . . ? C42B C41B C46B C45B -1.5(4) . . . . ? C30B C41B C46B C45B -179.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 22.72 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.374 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.044 #====================================================================== data_dds53 _database_code_depnum_ccdc_archive 'CCDC 641144' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'in paper 5e' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H24 O' _chemical_formula_weight 388.48 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' 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 8.5190(2) _cell_length_b 12.5850(3) _cell_length_c 10.24100(10) _cell_angle_alpha 73.0570(11) _cell_angle_beta 86.7680(12) _cell_angle_gamma 98.8770(9) _cell_volume 1031.73(4) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 3017 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 25.39 _exptl_crystal_description polyhedron _exptl_crystal_colour colorless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9647 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14378 _diffrn_reflns_av_R_equivalents 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 24.73 _reflns_number_total 14378 _reflns_number_gt 9690 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0520P)^2^+0.0175P] 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 14378 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1307 _refine_ls_wR_factor_gt 0.1122 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 0.29646(14) 0.75626(9) 1.02636(12) 0.0292(3) Uani 1 1 d . . . C2 C 0.17370(16) 0.65899(10) 1.00774(14) 0.0335(3) Uani 1 1 d . . . H2A H 0.1079(15) 0.6177(10) 1.0931(13) 0.036(4) Uiso 1 1 d . . . H2B H 0.2324(13) 0.6118(10) 0.9704(11) 0.032(3) Uiso 1 1 d . . . C3 C 0.07346(15) 0.71316(10) 0.89658(13) 0.0307(3) Uani 1 1 d . . . H3 H -0.0182(15) 0.7394(9) 0.9354(12) 0.036(3) Uiso 1 1 d . . . C4 C 0.01726(15) 0.63813(10) 0.80886(13) 0.0336(3) Uani 1 1 d . . . O4 O 0.09895(11) 0.57110(8) 0.79033(10) 0.0490(3) Uani 1 1 d . . . C11 C 0.45098(14) 0.72122(10) 1.07991(12) 0.0301(3) Uani 1 1 d . . . C12 C 0.56192(15) 0.79919(11) 1.11416(14) 0.0411(3) Uani 1 1 d . . . H12 H 0.5400 0.8727 1.1042 0.049 Uiso 1 1 calc R . . C13 C 0.70299(16) 0.77221(12) 1.16224(14) 0.0482(4) Uani 1 1 d . . . H13 H 0.7774 0.8272 1.1842 0.058 Uiso 1 1 calc R . . C14 C 0.73633(16) 0.66595(12) 1.17855(13) 0.0433(4) Uani 1 1 d . . . H14 H 0.8338 0.6472 1.2111 0.052 Uiso 1 1 calc R . . C15 C 0.62692(16) 0.58697(12) 1.14716(14) 0.0428(3) Uani 1 1 d . . . H15 H 0.6485 0.5130 1.1594 0.051 Uiso 1 1 calc R . . C16 C 0.48597(15) 0.61442(10) 1.09794(13) 0.0368(3) Uani 1 1 d . . . H16 H 0.4120 0.5591 1.0762 0.044 Uiso 1 1 calc R . . C21 C 0.21721(13) 0.80933(10) 1.12582(12) 0.0281(3) Uani 1 1 d . . . C22 C 0.18560(15) 0.74872(11) 1.26443(13) 0.0383(3) Uani 1 1 d . . . H22 H 0.2135 0.6760 1.2959 0.046 Uiso 1 1 calc R . . C23 C 0.11454(16) 0.79195(12) 1.35732(14) 0.0472(4) Uani 1 1 d . . . H23 H 0.0940 0.7488 1.4515 0.057 Uiso 1 1 calc R . . C24 C 0.07331(16) 0.89718(12) 1.31428(15) 0.0463(4) Uani 1 1 d . . . H24 H 0.0247 0.9271 1.3782 0.056 Uiso 1 1 calc R . . C25 C 0.10325(15) 0.95808(11) 1.17829(14) 0.0418(3) Uani 1 1 d . . . H25 H 0.0749 1.0308 1.1477 0.050 Uiso 1 1 calc R . . C26 C 0.17448(14) 0.91504(10) 1.08452(13) 0.0334(3) Uani 1 1 d . . . H26 H 0.1943 0.9587 0.9905 0.040 Uiso 1 1 calc R . . C31 C 0.32121(14) 0.83757(9) 0.88066(12) 0.0299(3) Uani 1 1 d . . . C32 C 0.44459(15) 0.92680(10) 0.81841(13) 0.0360(3) Uani 1 1 d . . . H32 H 0.5346 0.9411 0.8655 0.043 Uiso 1 1 calc R . . C33 C 0.43557(17) 0.99495(11) 0.68717(14) 0.0449(4) Uani 1 1 d . . . H33 H 0.5204 1.0559 0.6436 0.054 Uiso 1 1 calc R . . C34 C 0.30480(18) 0.97526(11) 0.61905(14) 0.0459(4) Uani 1 1 d . . . H34 H 0.2989 1.0237 0.5296 0.055 Uiso 1 1 calc R . . C35 C 0.18171(16) 0.88544(10) 0.67974(13) 0.0384(3) Uani 1 1 d . . . H35 H 0.0922 0.8713 0.6320 0.046 Uiso 1 1 calc R . . C36 C 0.19063(14) 0.81689(10) 0.81015(12) 0.0300(3) Uani 1 1 d . . . C41 C -0.12987(14) 0.65068(10) 0.74019(12) 0.0306(3) Uani 1 1 d . . . C42 C -0.15983(16) 0.59684(10) 0.64067(13) 0.0394(3) Uani 1 1 d . . . H42 H -0.0870 0.5523 0.6204 0.047 Uiso 1 1 calc R . . C43 C -0.29248(17) 0.60703(11) 0.57154(14) 0.0446(4) Uani 1 1 d . . . H43 H -0.3090 0.5709 0.5027 0.054 Uiso 1 1 calc R . . C44 C -0.40306(16) 0.66933(11) 0.60065(14) 0.0415(3) Uani 1 1 d . . . C45 C -0.37503(17) 0.72141(12) 0.70016(15) 0.0470(4) Uani 1 1 d . . . H45 H -0.4499 0.7640 0.7218 0.056 Uiso 1 1 calc R . . C46 C -0.24086(16) 0.71323(11) 0.76916(14) 0.0423(3) Uani 1 1 d . . . H46 H -0.2241 0.7505 0.8369 0.051 Uiso 1 1 calc R . . C47 C -0.55051(18) 0.67855(13) 0.52700(16) 0.0605(4) Uani 1 1 d . . . H47A H -0.5260 0.6784 0.4324 0.091 Uiso 1 1 calc R . . H47B H -0.5866 0.7490 0.5261 0.091 Uiso 1 1 calc R . . H47C H -0.6351 0.6143 0.5744 0.091 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 0.0269(7) 0.0264(6) 0.0353(7) -0.0108(6) -0.0050(6) 0.0038(5) C2 0.0338(8) 0.0292(7) 0.0364(8) -0.0094(7) -0.0063(6) 0.0026(6) C3 0.0286(7) 0.0308(7) 0.0343(7) -0.0115(6) -0.0055(6) 0.0063(6) C4 0.0310(7) 0.0289(7) 0.0403(8) -0.0117(6) -0.0012(6) 0.0023(6) O4 0.0399(6) 0.0493(6) 0.0739(7) -0.0360(6) -0.0187(5) 0.0180(5) C11 0.0282(7) 0.0316(7) 0.0310(7) -0.0105(6) -0.0037(5) 0.0050(6) C12 0.0335(8) 0.0368(8) 0.0557(9) -0.0175(7) -0.0119(7) 0.0058(6) C13 0.0342(8) 0.0539(9) 0.0577(10) -0.0208(8) -0.0130(7) 0.0013(7) C14 0.0291(8) 0.0620(10) 0.0389(8) -0.0109(7) -0.0077(6) 0.0153(7) C15 0.0424(9) 0.0437(8) 0.0456(9) -0.0127(7) -0.0079(7) 0.0179(7) C16 0.0342(8) 0.0365(7) 0.0408(8) -0.0125(6) -0.0070(6) 0.0074(6) C21 0.0204(6) 0.0325(7) 0.0320(7) -0.0115(6) -0.0070(5) 0.0017(5) C22 0.0362(8) 0.0391(7) 0.0384(8) -0.0087(6) -0.0074(6) 0.0075(6) C23 0.0434(9) 0.0646(10) 0.0332(8) -0.0153(7) 0.0002(7) 0.0093(8) C24 0.0389(8) 0.0672(10) 0.0448(9) -0.0305(8) -0.0082(7) 0.0180(8) C25 0.0373(8) 0.0460(8) 0.0512(9) -0.0230(7) -0.0110(7) 0.0160(7) C26 0.0318(7) 0.0355(7) 0.0347(7) -0.0122(6) -0.0069(6) 0.0071(6) C31 0.0315(7) 0.0269(6) 0.0334(7) -0.0130(6) 0.0002(6) 0.0058(6) C32 0.0337(8) 0.0319(7) 0.0428(8) -0.0156(6) 0.0021(6) 0.0011(6) C33 0.0504(9) 0.0336(7) 0.0432(9) -0.0084(7) 0.0131(7) -0.0023(7) C34 0.0615(10) 0.0376(8) 0.0332(8) -0.0043(7) 0.0027(7) 0.0083(7) C35 0.0455(9) 0.0366(7) 0.0344(8) -0.0114(6) -0.0055(6) 0.0099(7) C36 0.0333(7) 0.0276(6) 0.0321(7) -0.0131(6) -0.0027(6) 0.0069(6) C41 0.0302(7) 0.0275(6) 0.0324(7) -0.0086(6) -0.0040(6) 0.0005(5) C42 0.0400(8) 0.0377(8) 0.0429(8) -0.0162(7) -0.0046(7) 0.0061(6) C43 0.0507(9) 0.0471(8) 0.0389(8) -0.0192(7) -0.0133(7) 0.0022(7) C44 0.0383(8) 0.0405(8) 0.0410(8) -0.0064(7) -0.0108(7) 0.0024(7) C45 0.0417(9) 0.0540(9) 0.0559(9) -0.0254(8) -0.0171(7) 0.0195(7) C46 0.0415(9) 0.0470(8) 0.0491(9) -0.0259(7) -0.0144(7) 0.0144(7) C47 0.0530(10) 0.0652(10) 0.0625(11) -0.0144(9) -0.0283(8) 0.0097(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C31 1.5252(16) . ? C1 C11 1.5321(16) . ? C1 C2 1.5466(16) . ? C1 C21 1.5483(16) . ? C2 C3 1.5255(17) . ? C3 C36 1.5194(17) . ? C3 C4 1.5268(16) . ? C4 O4 1.2213(14) . ? C4 C41 1.4786(17) . ? C11 C16 1.3838(16) . ? C11 C12 1.3895(16) . ? C12 C13 1.3774(18) . ? C13 C14 1.3746(19) . ? C14 C15 1.3762(18) . ? C15 C16 1.3820(17) . ? C21 C26 1.3857(16) . ? C21 C22 1.3899(17) . ? C22 C23 1.3805(18) . ? C23 C24 1.3755(19) . ? C24 C25 1.3673(19) . ? C25 C26 1.3867(17) . ? C31 C32 1.3839(16) . ? C31 C36 1.3919(17) . ? C32 C33 1.3814(17) . ? C33 C34 1.3756(19) . ? C34 C35 1.3837(18) . ? C35 C36 1.3762(17) . ? C41 C46 1.3914(17) . ? C41 C42 1.3933(16) . ? C42 C43 1.3699(18) . ? C43 C44 1.3869(19) . ? C44 C45 1.3762(18) . ? C44 C47 1.5037(19) . ? C45 C46 1.3789(18) . ? 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 C31 C1 C11 113.57(10) . . ? C31 C1 C2 100.32(10) . . ? C11 C1 C2 114.47(10) . . ? C31 C1 C21 110.10(9) . . ? C11 C1 C21 109.09(9) . . ? C2 C1 C21 108.98(10) . . ? C3 C2 C1 106.47(10) . . ? C36 C3 C2 102.00(10) . . ? C36 C3 C4 110.13(10) . . ? C2 C3 C4 113.34(10) . . ? O4 C4 C41 119.97(11) . . ? O4 C4 C3 119.42(11) . . ? C41 C4 C3 120.52(11) . . ? C16 C11 C12 117.58(12) . . ? C16 C11 C1 123.30(11) . . ? C12 C11 C1 119.11(10) . . ? C13 C12 C11 121.47(12) . . ? C14 C13 C12 120.16(13) . . ? C13 C14 C15 119.28(13) . . ? C14 C15 C16 120.49(12) . . ? C15 C16 C11 121.01(12) . . ? C26 C21 C22 117.29(12) . . ? C26 C21 C1 123.60(11) . . ? C22 C21 C1 119.11(11) . . ? C23 C22 C21 121.43(12) . . ? C24 C23 C22 120.38(13) . . ? C25 C24 C23 119.08(13) . . ? C24 C25 C26 120.79(13) . . ? C21 C26 C25 121.04(12) . . ? C32 C31 C36 119.79(12) . . ? C32 C31 C1 129.59(11) . . ? C36 C31 C1 110.50(10) . . ? C33 C32 C31 119.36(12) . . ? C34 C33 C32 120.53(13) . . ? C33 C34 C35 120.55(13) . . ? C36 C35 C34 119.12(13) . . ? C35 C36 C31 120.63(12) . . ? C35 C36 C3 128.89(11) . . ? C31 C36 C3 110.47(11) . . ? C46 C41 C42 117.82(12) . . ? C46 C41 C4 123.82(11) . . ? C42 C41 C4 118.37(11) . . ? C43 C42 C41 121.13(12) . . ? C42 C43 C44 120.96(13) . . ? C45 C44 C43 118.09(13) . . ? C45 C44 C47 120.87(13) . . ? C43 C44 C47 121.03(13) . . ? C44 C45 C46 121.57(13) . . ? C45 C46 C41 120.42(13) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.73 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.167 _refine_diff_density_min -0.181 _refine_diff_density_rms 0.037 #====================================================================== data_dds14 _database_code_depnum_ccdc_archive 'CCDC 660693' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'in paper 2a' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H31 N O4' _chemical_formula_weight 553.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.348(2) _cell_length_b 8.806(1) _cell_length_c 22.612(4) _cell_angle_alpha 90.0 _cell_angle_beta 109.831(3) _cell_angle_gamma 90.0 _cell_volume 2874.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3761 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 28.07 _exptl_crystal_description irregular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.065 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9796 _exptl_absorpt_correction_T_max 0.9853 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _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 area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16360 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 21.96 _reflns_number_total 3488 _reflns_number_gt 2697 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+2.2654P] 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 3488 _refine_ls_number_parameters 509 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0685 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1164 _refine_ls_wR_factor_gt 0.1073 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.004 _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 0.02673(13) 0.2994(2) 0.50576(9) 0.0258(5) Uani 1 1 d . . . O2 O 0.38370(18) -0.2924(3) 0.61611(15) 0.0610(8) Uani 1 1 d . . . O3 O 0.4813(5) -0.2290(7) 0.6948(3) 0.0525(16) Uani 0.50 1 d P . . O3A O 0.5199(4) -0.1722(6) 0.6778(3) 0.0353(13) Uani 0.50 1 d P . . N1 N 0.4250(2) -0.1875(4) 0.64878(15) 0.0536(9) Uani 1 1 d . . . C1 C 0.14201(18) 0.3945(3) 0.59736(12) 0.0175(6) Uani 1 1 d . . . C3 C 0.2564(2) 0.4570(3) 0.69706(13) 0.0178(7) Uani 1 1 d . . . C4 C 0.18214(18) 0.5802(3) 0.68132(12) 0.0188(7) Uani 1 1 d . . . C5 C 0.1035(2) 0.5152(3) 0.63099(13) 0.0196(7) Uani 1 1 d . . . C6 C 0.0884(2) 0.3450(3) 0.63986(13) 0.0196(7) Uani 1 1 d . . . C7 C 0.1415(2) 0.2787(3) 0.70145(13) 0.0197(7) Uani 1 1 d . . . C8 C 0.2248(2) 0.3341(3) 0.73168(14) 0.0193(7) Uani 1 1 d . . . C9 C 0.0973(2) 0.3745(3) 0.52786(13) 0.0199(7) Uani 1 1 d . . . C10 C 0.14081(19) 0.4484(3) 0.48565(13) 0.0204(7) Uani 1 1 d . . . C11 C 0.1847(2) 0.5886(3) 0.49976(15) 0.0291(8) Uani 1 1 d . . . C12 C 0.2206(2) 0.6568(4) 0.45785(16) 0.0378(9) Uani 1 1 d . . . C13 C 0.2145(2) 0.5853(4) 0.40236(16) 0.0396(9) Uani 1 1 d . . . C14 C 0.1716(2) 0.4462(4) 0.38762(15) 0.0352(8) Uani 1 1 d . . . C15 C 0.1345(2) 0.3776(4) 0.42899(14) 0.0274(8) Uani 1 1 d . . . C16 C 0.24642(19) 0.3928(3) 0.63006(13) 0.0179(7) Uani 1 1 d . . . C17 C 0.29295(18) 0.2399(3) 0.63219(12) 0.0186(7) Uani 1 1 d . . . C18 C 0.3857(2) 0.2228(4) 0.66809(14) 0.0285(8) Uani 1 1 d . . . C19 C 0.4299(2) 0.0843(4) 0.67423(15) 0.0345(9) Uani 1 1 d . . . C20 C 0.3799(2) -0.0377(4) 0.64136(14) 0.0309(8) Uani 1 1 d . . . C21 C 0.2891(2) -0.0256(4) 0.60414(15) 0.0297(8) Uani 1 1 d . . . C22 C 0.2453(2) 0.1140(3) 0.59991(14) 0.0240(7) Uani 1 1 d . . . C23 C 0.18457(18) 0.7164(3) 0.70902(12) 0.0182(7) Uani 1 1 d . . . C24 C 0.26573(18) 0.7723(3) 0.76168(12) 0.0187(7) Uani 1 1 d . . . C25 C 0.3165(2) 0.6786(4) 0.81116(14) 0.0262(7) Uani 1 1 d . . . C26 C 0.3931(2) 0.7325(4) 0.85904(16) 0.0356(9) Uani 1 1 d . . . C27 C 0.4213(2) 0.8815(4) 0.85798(16) 0.0362(9) Uani 1 1 d . . . C28 C 0.3715(2) 0.9769(4) 0.81013(14) 0.0295(8) Uani 1 1 d . . . C29 C 0.2942(2) 0.9237(3) 0.76299(14) 0.0237(7) Uani 1 1 d . . . C30 C 0.10271(18) 0.8224(3) 0.68743(13) 0.0180(7) Uani 1 1 d . . . C31 C 0.0576(2) 0.8647(3) 0.72912(15) 0.0239(7) Uani 1 1 d . . . C32 C -0.0182(2) 0.9610(3) 0.71074(16) 0.0281(8) Uani 1 1 d . . . C33 C -0.0495(2) 1.0190(3) 0.65023(15) 0.0280(8) Uani 1 1 d . . . C34 C -0.0052(2) 0.9798(3) 0.60843(15) 0.0277(8) Uani 1 1 d . . . C35 C 0.0696(2) 0.8822(3) 0.62680(14) 0.0225(7) Uani 1 1 d . . . H3 H 0.3186(18) 0.494(3) 0.7201(11) 0.010(6) Uiso 1 1 d . . . H5 H 0.0496(18) 0.573(3) 0.6091(12) 0.012(7) Uiso 1 1 d . . . H6 H 0.029(2) 0.311(3) 0.6168(12) 0.019(7) Uiso 1 1 d . . . H7 H 0.1174(19) 0.200(3) 0.7195(13) 0.026(8) Uiso 1 1 d . . . H8 H 0.2646(18) 0.300(3) 0.7733(13) 0.020(7) Uiso 1 1 d . . . H11 H 0.1908(18) 0.640(3) 0.5382(14) 0.023(8) Uiso 1 1 d . . . H12 H 0.252(2) 0.755(4) 0.4688(15) 0.043(9) Uiso 1 1 d . . . H13 H 0.238(2) 0.632(3) 0.3720(15) 0.038(9) Uiso 1 1 d . . . H14 H 0.168(2) 0.388(3) 0.3455(15) 0.038(8) Uiso 1 1 d . . . H15 H 0.103(2) 0.282(3) 0.4202(13) 0.029(8) Uiso 1 1 d . . . H16 H 0.2751(16) 0.466(3) 0.6118(11) 0.004(6) Uiso 1 1 d . . . H18 H 0.420(2) 0.305(3) 0.6897(13) 0.026(8) Uiso 1 1 d . . . H19 H 0.492(2) 0.071(3) 0.7000(15) 0.041(9) Uiso 1 1 d . . . H21 H 0.258(2) -0.114(4) 0.5813(14) 0.032(8) Uiso 1 1 d . . . H22 H 0.178(2) 0.122(3) 0.5748(14) 0.032(8) Uiso 1 1 d . . . H25 H 0.2955(18) 0.581(3) 0.8122(12) 0.022(8) Uiso 1 1 d . . . H26 H 0.427(2) 0.669(3) 0.8926(14) 0.028(8) Uiso 1 1 d . . . H27 H 0.476(2) 0.917(4) 0.8905(15) 0.041(9) Uiso 1 1 d . . . H28 H 0.3909(19) 1.085(3) 0.8089(13) 0.028(8) Uiso 1 1 d . . . H29 H 0.2569(19) 0.992(3) 0.7287(13) 0.022(7) Uiso 1 1 d . . . H31 H 0.0793(18) 0.822(3) 0.7710(14) 0.026(8) Uiso 1 1 d . . . H32 H -0.050(2) 0.984(3) 0.7395(14) 0.033(9) Uiso 1 1 d . . . H33 H -0.1021(19) 1.087(3) 0.6371(12) 0.019(7) Uiso 1 1 d . . . H34 H -0.027(2) 1.023(3) 0.5659(16) 0.040(9) Uiso 1 1 d . . . H35 H 0.0974(19) 0.849(3) 0.5974(13) 0.024(8) Uiso 1 1 d . . . O50 O 0.5830(5) 0.8589(7) 0.6076(3) 0.092(2) Uani 0.50 1 d P A 1 C50 C 0.6140(6) 0.8271(8) 0.5646(5) 0.0449(19) Uani 0.50 1 d P A 1 C51 C 0.6943(7) 0.9148(11) 0.5623(5) 0.072(2) Uani 0.50 1 d P A 1 H51A H 0.7123 0.8794 0.5270 0.109 Uiso 0.50 1 calc PR A 1 H51B H 0.7462 0.9008 0.6016 0.109 Uiso 0.50 1 calc PR A 1 H51C H 0.6780 1.0227 0.5566 0.109 Uiso 0.50 1 calc PR A 1 O50A O 0.4930(5) 0.9416(7) 0.5343(3) 0.085(2) Uani 0.50 1 d P A 2 C50A C 0.5503(8) 0.8594(10) 0.5298(4) 0.055(2) Uani 0.50 1 d P A 2 C51A C 0.6291(7) 0.9211(11) 0.5177(5) 0.072(2) Uani 0.50 1 d P A 2 H51D H 0.6268 1.0322 0.5189 0.109 Uiso 0.50 1 calc PR A 2 H51E H 0.6282 0.8881 0.4761 0.109 Uiso 0.50 1 calc PR A 2 H51F H 0.6860 0.8851 0.5498 0.109 Uiso 0.50 1 calc PR A 2 C52 C 0.5653(4) 0.6986(5) 0.5273(2) 0.126(3) Uani 1 1 d . . . H52A H 0.5160 0.6650 0.5428 0.189 Uiso 1 1 calc R A 1 H52B H 0.6090 0.6150 0.5308 0.189 Uiso 1 1 calc R A 1 H52C H 0.5381 0.7292 0.4831 0.189 Uiso 1 1 calc R A 1 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 0.0257(12) 0.0261(12) 0.0224(11) -0.0030(9) 0.0038(9) -0.0063(10) O2 0.0543(17) 0.0283(15) 0.106(2) 0.0049(16) 0.0342(16) 0.0115(13) O3 0.062(4) 0.053(4) 0.030(3) 0.001(3) -0.001(3) 0.035(3) O3A 0.033(3) 0.029(3) 0.039(3) 0.004(2) 0.006(3) 0.012(2) N1 0.066(2) 0.052(2) 0.037(2) -0.0002(17) 0.0101(18) 0.040(2) C1 0.0189(15) 0.0132(15) 0.0205(16) 0.0007(12) 0.0070(13) -0.0001(12) C3 0.0161(16) 0.0175(16) 0.0186(16) -0.0011(13) 0.0042(13) -0.0008(13) C4 0.0208(16) 0.0179(17) 0.0175(16) 0.0018(13) 0.0060(13) -0.0038(13) C5 0.0207(17) 0.0154(16) 0.0230(17) 0.0024(13) 0.0077(14) 0.0029(13) C6 0.0193(17) 0.0155(16) 0.0241(17) -0.0027(13) 0.0075(14) -0.0027(13) C7 0.0269(18) 0.0135(16) 0.0229(17) -0.0014(14) 0.0138(15) -0.0001(14) C8 0.0245(18) 0.0175(16) 0.0167(17) -0.0019(13) 0.0083(14) 0.0042(13) C9 0.0222(17) 0.0148(15) 0.0218(17) -0.0022(13) 0.0061(13) 0.0038(14) C10 0.0216(16) 0.0205(17) 0.0172(16) 0.0018(13) 0.0040(13) 0.0012(13) C11 0.040(2) 0.0234(19) 0.0221(18) 0.0004(15) 0.0078(15) -0.0042(15) C12 0.049(2) 0.030(2) 0.033(2) 0.0080(17) 0.0122(17) -0.0096(17) C13 0.042(2) 0.052(2) 0.029(2) 0.0169(19) 0.0172(17) 0.0022(18) C14 0.037(2) 0.045(2) 0.026(2) 0.0009(17) 0.0136(16) 0.0019(17) C15 0.0270(17) 0.0281(19) 0.0253(19) -0.0001(15) 0.0067(14) 0.0002(15) C16 0.0211(16) 0.0142(16) 0.0201(16) 0.0019(13) 0.0094(13) -0.0035(13) C17 0.0201(16) 0.0235(17) 0.0150(15) 0.0007(13) 0.0098(13) 0.0012(13) C18 0.0220(18) 0.034(2) 0.0281(18) -0.0048(16) 0.0074(15) 0.0017(17) C19 0.0237(19) 0.054(2) 0.0243(18) -0.0038(17) 0.0058(15) 0.0142(18) C20 0.038(2) 0.031(2) 0.0246(18) 0.0005(15) 0.0123(16) 0.0188(16) C21 0.034(2) 0.0230(19) 0.0329(19) -0.0032(15) 0.0128(16) 0.0062(16) C22 0.0228(18) 0.0234(18) 0.0258(17) -0.0006(14) 0.0083(15) 0.0023(14) C23 0.0214(16) 0.0184(16) 0.0159(16) 0.0009(13) 0.0079(12) -0.0029(13) C24 0.0210(16) 0.0174(16) 0.0191(16) -0.0043(13) 0.0086(13) 0.0017(13) C25 0.0315(18) 0.0164(18) 0.0274(19) -0.0067(15) 0.0054(15) 0.0018(15) C26 0.034(2) 0.034(2) 0.028(2) -0.0038(17) -0.0034(16) 0.0072(17) C27 0.0269(19) 0.040(2) 0.035(2) -0.0123(18) 0.0020(17) -0.0034(17) C28 0.0309(19) 0.029(2) 0.0297(19) -0.0065(16) 0.0124(16) -0.0071(16) C29 0.0268(17) 0.0226(18) 0.0226(18) -0.0040(15) 0.0096(15) -0.0032(14) C30 0.0206(16) 0.0102(15) 0.0220(17) -0.0023(13) 0.0055(13) -0.0051(12) C31 0.0264(18) 0.0176(17) 0.0282(19) 0.0035(15) 0.0100(15) -0.0039(14) C32 0.0264(18) 0.0206(18) 0.043(2) 0.0010(16) 0.0195(17) -0.0031(15) C33 0.0207(17) 0.0142(16) 0.045(2) -0.0009(15) 0.0053(16) 0.0006(14) C34 0.0296(19) 0.0158(17) 0.029(2) -0.0010(15) -0.0016(16) -0.0016(15) C35 0.0271(18) 0.0157(16) 0.0236(18) -0.0038(14) 0.0073(15) -0.0019(14) O50 0.123(6) 0.078(5) 0.093(5) -0.020(4) 0.062(5) -0.047(4) C50 0.057(6) 0.033(5) 0.049(5) -0.003(4) 0.025(5) -0.007(4) C51 0.099(7) 0.062(4) 0.071(6) -0.004(5) 0.050(4) 0.000(5) O50A 0.088(5) 0.054(4) 0.099(5) -0.022(3) 0.015(4) 0.016(4) C50A 0.084(7) 0.043(6) 0.034(5) 0.001(4) 0.013(5) -0.008(5) C51A 0.099(7) 0.062(4) 0.071(6) -0.004(5) 0.050(4) 0.000(5) C52 0.173(6) 0.056(3) 0.087(4) -0.008(3) -0.038(4) 0.034(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 O1 C9 1.222(3) . ? O2 N1 1.218(4) . ? O3 O3A 0.952(6) . ? O3 N1 1.164(6) . ? O3A N1 1.387(6) . ? N1 C20 1.473(4) . ? C1 C9 1.497(4) . ? C1 C16 1.520(4) . ? C1 C6 1.525(4) . ? C1 C5 1.538(4) . ? C3 C8 1.509(4) . ? C3 C4 1.526(4) . ? C3 C16 1.575(4) . ? C3 H3 0.97(3) . ? C4 C23 1.348(4) . ? C4 C5 1.466(4) . ? C5 C6 1.541(4) . ? C5 H5 0.95(3) . ? C6 C7 1.475(4) . ? C6 H6 0.93(3) . ? C7 C8 1.321(4) . ? C7 H7 0.94(3) . ? C8 H8 0.98(3) . ? C9 C10 1.487(4) . ? C10 C11 1.391(4) . ? C10 C15 1.398(4) . ? C11 C12 1.384(4) . ? C11 H11 0.96(3) . ? C12 C13 1.378(5) . ? C12 H12 0.98(3) . ? C13 C14 1.378(5) . ? C13 H13 0.96(3) . ? C14 C15 1.387(4) . ? C14 H14 1.06(3) . ? C15 H15 0.96(3) . ? C16 C17 1.517(4) . ? C16 H16 0.95(2) . ? C17 C18 1.386(4) . ? C17 C22 1.391(4) . ? C18 C19 1.380(4) . ? C18 H18 0.93(3) . ? C19 C20 1.381(5) . ? C19 H19 0.95(3) . ? C20 C21 1.366(4) . ? C21 C22 1.389(4) . ? C21 H21 0.96(3) . ? C22 H22 1.00(3) . ? C23 C24 1.485(4) . ? C23 C30 1.507(4) . ? C24 C25 1.395(4) . ? C24 C29 1.400(4) . ? C25 C26 1.385(4) . ? C25 H25 0.92(3) . ? C26 C27 1.385(5) . ? C26 H26 0.95(3) . ? C27 C28 1.378(5) . ? C27 H27 0.96(3) . ? C28 C29 1.380(4) . ? C28 H28 1.00(3) . ? C29 H29 1.00(3) . ? C30 C35 1.394(4) . ? C30 C31 1.396(4) . ? C31 C32 1.384(4) . ? C31 H31 0.97(3) . ? C32 C33 1.385(4) . ? C32 H32 0.95(3) . ? C33 C34 1.382(5) . ? C33 H33 0.97(3) . ? C34 C35 1.381(4) . ? C34 H34 0.98(3) . ? C35 H35 0.95(3) . ? O50 C50 1.250(9) . ? C50 C52 1.458(9) . ? C50 C51 1.471(12) . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? O50A C50A 1.170(11) . ? C50A C52 1.439(10) . ? C50A C51A 1.434(13) . ? C51A H51D 0.9800 . ? C51A H51E 0.9800 . ? C51A H51F 0.9800 . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? 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 O3A O3 N1 81.3(6) . . ? O3 O3A N1 56.0(5) . . ? O3 N1 O2 112.3(5) . . ? O3 N1 O3A 42.7(3) . . ? O2 N1 O3A 127.4(3) . . ? O3 N1 C20 124.1(4) . . ? O2 N1 C20 118.8(3) . . ? O3A N1 C20 110.2(4) . . ? C9 C1 C16 122.8(2) . . ? C9 C1 C6 118.3(2) . . ? C16 C1 C6 113.3(2) . . ? C9 C1 C5 119.0(2) . . ? C16 C1 C5 106.6(2) . . ? C6 C1 C5 60.39(18) . . ? C8 C3 C4 106.5(2) . . ? C8 C3 C16 107.3(2) . . ? C4 C3 C16 102.1(2) . . ? C8 C3 H3 113.1(14) . . ? C4 C3 H3 113.9(14) . . ? C16 C3 H3 113.1(14) . . ? C23 C4 C5 126.4(3) . . ? C23 C4 C3 128.6(2) . . ? C5 C4 C3 104.9(2) . . ? C4 C5 C1 107.4(2) . . ? C4 C5 C6 113.5(2) . . ? C1 C5 C6 59.41(18) . . ? C4 C5 H5 122.3(15) . . ? C1 C5 H5 121.6(15) . . ? C6 C5 H5 116.5(15) . . ? C7 C6 C1 117.7(2) . . ? C7 C6 C5 116.7(2) . . ? C1 C6 C5 60.20(18) . . ? C7 C6 H6 121.7(17) . . ? C1 C6 H6 111.7(16) . . ? C5 C6 H6 113.6(17) . . ? C8 C7 C6 118.1(3) . . ? C8 C7 H7 120.0(17) . . ? C6 C7 H7 121.9(17) . . ? C7 C8 C3 114.9(3) . . ? C7 C8 H8 124.3(16) . . ? C3 C8 H8 120.7(16) . . ? O1 C9 C10 120.2(2) . . ? O1 C9 C1 121.3(2) . . ? C10 C9 C1 118.5(2) . . ? C11 C10 C15 118.9(3) . . ? C11 C10 C9 121.9(3) . . ? C15 C10 C9 119.1(3) . . ? C12 C11 C10 120.2(3) . . ? C12 C11 H11 118.4(16) . . ? C10 C11 H11 121.4(16) . . ? C13 C12 C11 120.3(3) . . ? C13 C12 H12 120.5(19) . . ? C11 C12 H12 119.1(19) . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13 117.7(18) . . ? C12 C13 H13 121.9(19) . . ? C13 C14 C15 119.7(3) . . ? C13 C14 H14 121.2(16) . . ? C15 C14 H14 119.0(16) . . ? C14 C15 C10 120.5(3) . . ? C14 C15 H15 122.5(17) . . ? C10 C15 H15 117.0(17) . . ? C17 C16 C1 115.6(2) . . ? C17 C16 C3 113.4(2) . . ? C1 C16 C3 101.9(2) . . ? C17 C16 H16 109.4(14) . . ? C1 C16 H16 110.5(14) . . ? C3 C16 H16 105.5(14) . . ? C18 C17 C22 118.3(3) . . ? C18 C17 C16 119.6(3) . . ? C22 C17 C16 122.2(2) . . ? C19 C18 C17 121.8(3) . . ? C19 C18 H18 117.5(17) . . ? C17 C18 H18 120.7(17) . . ? C18 C19 C20 117.9(3) . . ? C18 C19 H19 122.2(19) . . ? C20 C19 H19 119.9(19) . . ? C21 C20 C19 122.4(3) . . ? C21 C20 N1 118.8(3) . . ? C19 C20 N1 118.8(3) . . ? C20 C21 C22 118.7(3) . . ? C20 C21 H21 118.8(18) . . ? C22 C21 H21 122.4(18) . . ? C21 C22 C17 120.8(3) . . ? C21 C22 H22 119.2(17) . . ? C17 C22 H22 119.9(16) . . ? C4 C23 C24 123.4(2) . . ? C4 C23 C30 120.8(2) . . ? C24 C23 C30 115.8(2) . . ? C25 C24 C29 117.4(3) . . ? C25 C24 C23 122.4(3) . . ? C29 C24 C23 120.2(2) . . ? C26 C25 C24 121.3(3) . . ? C26 C25 H25 120.8(17) . . ? C24 C25 H25 117.8(17) . . ? C25 C26 C27 119.9(3) . . ? C25 C26 H26 121.0(18) . . ? C27 C26 H26 119.1(18) . . ? C28 C27 C26 119.9(3) . . ? C28 C27 H27 120.8(19) . . ? C26 C27 H27 119.3(19) . . ? C29 C28 C27 120.1(3) . . ? C29 C28 H28 119.2(16) . . ? C27 C28 H28 120.7(16) . . ? C28 C29 C24 121.3(3) . . ? C28 C29 H29 120.8(16) . . ? C24 C29 H29 117.9(16) . . ? C35 C30 C31 117.7(3) . . ? C35 C30 C23 122.6(2) . . ? C31 C30 C23 119.8(2) . . ? C32 C31 C30 121.3(3) . . ? C32 C31 H31 120.3(16) . . ? C30 C31 H31 118.3(16) . . ? C31 C32 C33 119.8(3) . . ? C31 C32 H32 119.6(18) . . ? C33 C32 H32 120.6(18) . . ? C34 C33 C32 119.9(3) . . ? C34 C33 H33 119.8(16) . . ? C32 C33 H33 120.3(16) . . ? C35 C34 C33 120.1(3) . . ? C35 C34 H34 120.9(18) . . ? C33 C34 H34 119.1(18) . . ? C34 C35 C30 121.3(3) . . ? C34 C35 H35 120.5(17) . . ? C30 C35 H35 118.0(17) . . ? O50 C50 C52 111.6(7) . . ? O50 C50 C51 117.1(8) . . ? C52 C50 C51 131.2(8) . . ? C50 C51 H51A 109.5 . . ? C50 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C50 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? O50A C50A C52 138.3(9) . . ? O50A C50A C51A 119.3(8) . . ? C52 C50A C51A 102.1(9) . . ? C50A C51A H51D 109.5 . . ? C50A C51A H51E 109.5 . . ? H51D C51A H51E 109.5 . . ? C50A C51A H51F 109.5 . . ? H51D C51A H51F 109.5 . . ? H51E C51A H51F 109.5 . . ? C50A C52 C50 43.1(4) . . ? C50A C52 H52A 97.5 . . ? C50 C52 H52A 109.5 . . ? C50A C52 H52B 148.2 . . ? C50 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? C50A C52 H52C 75.5 . . ? C50 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? 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 O3A O3 N1 O2 121.6(6) . . . . ? O3A O3 N1 C20 -83.1(7) . . . . ? O3 O3A N1 O2 -82.9(7) . . . . ? O3 O3A N1 C20 118.9(6) . . . . ? C8 C3 C4 C23 104.1(3) . . . . ? C16 C3 C4 C23 -143.5(3) . . . . ? C8 C3 C4 C5 -72.7(3) . . . . ? C16 C3 C4 C5 39.7(3) . . . . ? C23 C4 C5 C1 158.2(3) . . . . ? C3 C4 C5 C1 -24.9(3) . . . . ? C23 C4 C5 C6 -138.3(3) . . . . ? C3 C4 C5 C6 38.6(3) . . . . ? C9 C1 C5 C4 -144.5(2) . . . . ? C16 C1 C5 C4 -0.3(3) . . . . ? C6 C1 C5 C4 107.5(3) . . . . ? C9 C1 C5 C6 108.0(3) . . . . ? C16 C1 C5 C6 -107.8(2) . . . . ? C9 C1 C6 C7 144.5(3) . . . . ? C16 C1 C6 C7 -10.0(3) . . . . ? C5 C1 C6 C7 -106.5(3) . . . . ? C9 C1 C6 C5 -109.1(3) . . . . ? C16 C1 C6 C5 96.5(2) . . . . ? C4 C5 C6 C7 11.1(3) . . . . ? C1 C5 C6 C7 108.1(3) . . . . ? C4 C5 C6 C1 -97.0(3) . . . . ? C1 C6 C7 C8 36.1(4) . . . . ? C5 C6 C7 C8 -32.5(4) . . . . ? C6 C7 C8 C3 -2.2(4) . . . . ? C4 C3 C8 C7 55.5(3) . . . . ? C16 C3 C8 C7 -53.3(3) . . . . ? C16 C1 C9 O1 140.5(3) . . . . ? C6 C1 C9 O1 -11.5(4) . . . . ? C5 C1 C9 O1 -81.4(3) . . . . ? C16 C1 C9 C10 -39.5(4) . . . . ? C6 C1 C9 C10 168.6(2) . . . . ? C5 C1 C9 C10 98.7(3) . . . . ? O1 C9 C10 C11 145.1(3) . . . . ? C1 C9 C10 C11 -35.0(4) . . . . ? O1 C9 C10 C15 -32.5(4) . . . . ? C1 C9 C10 C15 147.5(3) . . . . ? C15 C10 C11 C12 0.6(4) . . . . ? C9 C10 C11 C12 -177.0(3) . . . . ? C10 C11 C12 C13 -1.1(5) . . . . ? C11 C12 C13 C14 0.9(5) . . . . ? C12 C13 C14 C15 -0.2(5) . . . . ? C13 C14 C15 C10 -0.4(5) . . . . ? C11 C10 C15 C14 0.1(4) . . . . ? C9 C10 C15 C14 177.8(3) . . . . ? C9 C1 C16 C17 -69.8(3) . . . . ? C6 C1 C16 C17 83.4(3) . . . . ? C5 C1 C16 C17 147.7(2) . . . . ? C9 C1 C16 C3 166.8(2) . . . . ? C6 C1 C16 C3 -40.1(3) . . . . ? C5 C1 C16 C3 24.3(3) . . . . ? C8 C3 C16 C17 -51.9(3) . . . . ? C4 C3 C16 C17 -163.8(2) . . . . ? C8 C3 C16 C1 73.0(3) . . . . ? C4 C3 C16 C1 -38.9(3) . . . . ? C1 C16 C17 C18 -171.5(3) . . . . ? C3 C16 C17 C18 -54.3(3) . . . . ? C1 C16 C17 C22 7.5(4) . . . . ? C3 C16 C17 C22 124.7(3) . . . . ? C22 C17 C18 C19 -2.5(4) . . . . ? C16 C17 C18 C19 176.5(3) . . . . ? C17 C18 C19 C20 2.5(5) . . . . ? C18 C19 C20 C21 -0.7(5) . . . . ? C18 C19 C20 N1 -178.2(3) . . . . ? O3 N1 C20 C21 -145.5(6) . . . . ? O2 N1 C20 C21 8.3(5) . . . . ? O3A N1 C20 C21 168.6(4) . . . . ? O3 N1 C20 C19 32.0(7) . . . . ? O2 N1 C20 C19 -174.2(3) . . . . ? O3A N1 C20 C19 -13.8(5) . . . . ? C19 C20 C21 C22 -0.9(5) . . . . ? N1 C20 C21 C22 176.6(3) . . . . ? C20 C21 C22 C17 0.9(4) . . . . ? C18 C17 C22 C21 0.8(4) . . . . ? C16 C17 C22 C21 -178.2(3) . . . . ? C5 C4 C23 C24 177.4(3) . . . . ? C3 C4 C23 C24 1.3(4) . . . . ? C5 C4 C23 C30 -2.6(4) . . . . ? C3 C4 C23 C30 -178.7(2) . . . . ? C4 C23 C24 C25 -41.5(4) . . . . ? C30 C23 C24 C25 138.5(3) . . . . ? C4 C23 C24 C29 138.4(3) . . . . ? C30 C23 C24 C29 -41.6(3) . . . . ? C29 C24 C25 C26 -1.3(4) . . . . ? C23 C24 C25 C26 178.6(3) . . . . ? C24 C25 C26 C27 -0.7(5) . . . . ? C25 C26 C27 C28 1.7(5) . . . . ? C26 C27 C28 C29 -0.7(5) . . . . ? C27 C28 C29 C24 -1.4(5) . . . . ? C25 C24 C29 C28 2.3(4) . . . . ? C23 C24 C29 C28 -177.5(3) . . . . ? C4 C23 C30 C35 -62.0(4) . . . . ? C24 C23 C30 C35 118.0(3) . . . . ? C4 C23 C30 C31 118.5(3) . . . . ? C24 C23 C30 C31 -61.5(3) . . . . ? C35 C30 C31 C32 0.9(4) . . . . ? C23 C30 C31 C32 -179.5(3) . . . . ? C30 C31 C32 C33 -1.1(4) . . . . ? C31 C32 C33 C34 0.4(4) . . . . ? C32 C33 C34 C35 0.5(4) . . . . ? C33 C34 C35 C30 -0.7(4) . . . . ? C31 C30 C35 C34 0.0(4) . . . . ? C23 C30 C35 C34 -179.6(3) . . . . ? O50A C50A C52 C50 -126.0(14) . . . . ? C51A C50A C52 C50 60.3(9) . . . . ? O50 C50 C52 C50A 81.9(9) . . . . ? C51 C50 C52 C50A -102.5(14) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 21.96 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.539 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.041 #====================================================================== data_wl1 _database_code_depnum_ccdc_archive 'CCDC 660694' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'in paper 11f' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H24 O2' _chemical_formula_weight 404.48 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pccn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 15.277(3) _cell_length_b 37.640(8) _cell_length_c 7.251(2) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 4169.4(15) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1138 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 24.96 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9859 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details 'Blessing, Acta Cryst. (1995) A51 33-38.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10547 _diffrn_reflns_av_R_equivalents 0.0737 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 20.81 _reflns_number_total 2173 _reflns_number_gt 1621 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0553P)^2^+5.8185P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2173 _refine_ls_number_parameters 281 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1415 _refine_ls_wR_factor_gt 0.1327 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 O10 O 0.58091(19) 0.45344(7) 0.1516(4) 0.0303(8) Uani 1 1 d . . . O14 O 0.34007(19) 0.57512(7) 0.4487(4) 0.0305(8) Uani 1 1 d . . . C1 C 0.4946(3) 0.35151(11) 0.1048(6) 0.0261(11) Uani 1 1 d . . . C2 C 0.5365(3) 0.38299(11) 0.2135(7) 0.0326(12) Uani 1 1 d . . . H2A H 0.5525 0.3754 0.3398 0.039 Uiso 1 1 calc R . . H2B H 0.5900 0.3915 0.1501 0.039 Uiso 1 1 calc R . . C3 C 0.4668(3) 0.41271(10) 0.2201(6) 0.0247(11) Uani 1 1 d . . . H3 H 0.4298 0.4101 0.3331 0.030 Uiso 1 1 calc R . . C4 C 0.4129(3) 0.40530(11) 0.0496(6) 0.0216(11) Uani 1 1 d . . . C5 C 0.3547(3) 0.42767(11) -0.0429(6) 0.0240(11) Uani 1 1 d . . . H5 H 0.3414 0.4506 0.0047 0.029 Uiso 1 1 calc R . . C6 C 0.3170(3) 0.41609(12) -0.2036(6) 0.0289(12) Uani 1 1 d . . . H6 H 0.2780 0.4312 -0.2685 0.035 Uiso 1 1 calc R . . C7 C 0.3352(3) 0.38242(12) -0.2730(7) 0.0319(12) Uani 1 1 d . . . H7 H 0.3082 0.3748 -0.3843 0.038 Uiso 1 1 calc R . . C8 C 0.3917(3) 0.36009(12) -0.1823(6) 0.0317(12) Uani 1 1 d . . . H8 H 0.4041 0.3371 -0.2301 0.038 Uiso 1 1 calc R . . C9 C 0.4306(3) 0.37162(11) -0.0187(6) 0.0234(11) Uani 1 1 d . . . C10 C 0.5070(3) 0.44980(11) 0.2135(6) 0.0214(11) Uani 1 1 d . . . C11 C 0.4576(3) 0.48135(10) 0.2771(6) 0.0191(10) Uani 1 1 d . . . C12 C 0.3779(3) 0.47977(11) 0.3692(6) 0.0273(12) Uani 1 1 d . . . H12 H 0.3517 0.4573 0.3925 0.033 Uiso 1 1 calc R . . C13 C 0.3362(3) 0.51045(11) 0.4278(6) 0.0269(12) Uani 1 1 d . . . H13 H 0.2817 0.5090 0.4905 0.032 Uiso 1 1 calc R . . C14 C 0.3740(3) 0.54299(11) 0.3945(6) 0.0226(11) Uani 1 1 d . . . C15 C 0.4529(3) 0.54499(11) 0.3022(6) 0.0262(11) Uani 1 1 d . . . H15 H 0.4791 0.5675 0.2794 0.031 Uiso 1 1 calc R . . C16 C 0.4934(3) 0.51444(11) 0.2433(6) 0.0251(11) Uani 1 1 d . . . H16 H 0.5471 0.5161 0.1779 0.030 Uiso 1 1 calc R . . C17 C 0.2674(3) 0.57429(12) 0.5735(6) 0.0339(12) Uani 1 1 d . . . H17A H 0.2159 0.5647 0.5102 0.051 Uiso 1 1 calc R . . H17B H 0.2547 0.5984 0.6164 0.051 Uiso 1 1 calc R . . H17C H 0.2818 0.5592 0.6794 0.051 Uiso 1 1 calc R . . C31 C 0.4472(3) 0.32655(11) 0.2375(6) 0.0278(12) Uani 1 1 d . . . C32 C 0.4932(3) 0.31150(12) 0.3836(7) 0.0354(13) Uani 1 1 d . . . H32 H 0.5532 0.3173 0.3996 0.042 Uiso 1 1 calc R . . C33 C 0.4538(4) 0.28820(13) 0.5068(7) 0.0448(14) Uani 1 1 d . . . H33 H 0.4871 0.2781 0.6042 0.054 Uiso 1 1 calc R . . C34 C 0.3665(4) 0.27974(13) 0.4879(7) 0.0444(15) Uani 1 1 d . . . H34 H 0.3392 0.2637 0.5711 0.053 Uiso 1 1 calc R . . C35 C 0.3189(3) 0.29510(12) 0.3449(7) 0.0422(14) Uani 1 1 d . . . H35 H 0.2584 0.2898 0.3317 0.051 Uiso 1 1 calc R . . C36 C 0.3587(3) 0.31804(12) 0.2220(7) 0.0324(12) Uani 1 1 d . . . H36 H 0.3251 0.3282 0.1251 0.039 Uiso 1 1 calc R . . C41 C 0.5629(3) 0.33179(11) -0.0151(7) 0.0300(12) Uani 1 1 d . . . C42 C 0.6114(3) 0.35078(13) -0.1422(7) 0.0360(13) Uani 1 1 d . . . H42 H 0.6029 0.3757 -0.1531 0.043 Uiso 1 1 calc R . . C43 C 0.6722(3) 0.33398(13) -0.2543(7) 0.0431(14) Uani 1 1 d . . . H43 H 0.7051 0.3475 -0.3405 0.052 Uiso 1 1 calc R . . C44 C 0.6856(3) 0.29806(14) -0.2421(7) 0.0410(14) Uani 1 1 d . . . H44 H 0.7279 0.2868 -0.3181 0.049 Uiso 1 1 calc R . . C45 C 0.6374(3) 0.27864(13) -0.1195(7) 0.0379(14) Uani 1 1 d . . . H45 H 0.6459 0.2537 -0.1114 0.046 Uiso 1 1 calc R . . C46 C 0.5758(3) 0.29521(12) -0.0059(7) 0.0340(13) Uani 1 1 d . . . H46 H 0.5424 0.2814 0.0782 0.041 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 O10 0.0263(19) 0.0298(19) 0.035(2) -0.0033(15) 0.0051(16) -0.0013(16) O14 0.0273(18) 0.0274(19) 0.037(2) -0.0067(16) 0.0034(16) 0.0056(15) C1 0.027(3) 0.024(2) 0.028(3) -0.005(2) -0.003(2) 0.004(2) C2 0.035(3) 0.027(3) 0.036(3) -0.002(2) -0.009(3) 0.001(2) C3 0.031(3) 0.023(3) 0.020(3) -0.003(2) -0.002(2) -0.001(2) C4 0.018(2) 0.024(3) 0.023(3) -0.004(2) 0.004(2) -0.002(2) C5 0.016(2) 0.024(2) 0.033(3) 0.000(2) 0.002(2) 0.000(2) C6 0.020(3) 0.037(3) 0.029(3) 0.006(2) -0.003(2) 0.000(2) C7 0.030(3) 0.039(3) 0.027(3) -0.002(3) -0.009(2) -0.005(3) C8 0.032(3) 0.029(3) 0.034(3) -0.004(3) -0.002(3) 0.000(2) C9 0.022(2) 0.028(3) 0.021(3) -0.005(2) -0.002(2) -0.002(2) C10 0.023(3) 0.026(3) 0.016(3) -0.001(2) -0.002(2) -0.001(2) C11 0.022(2) 0.020(3) 0.015(2) 0.001(2) -0.001(2) 0.000(2) C12 0.033(3) 0.022(3) 0.027(3) -0.004(2) -0.002(2) -0.006(2) C13 0.024(3) 0.031(3) 0.026(3) -0.002(2) 0.004(2) -0.002(2) C14 0.027(3) 0.022(3) 0.019(3) 0.000(2) -0.003(2) 0.004(2) C15 0.031(3) 0.024(3) 0.024(3) 0.002(2) -0.002(2) -0.005(2) C16 0.024(2) 0.025(3) 0.026(3) -0.002(2) 0.002(2) 0.001(2) C17 0.027(3) 0.043(3) 0.031(3) -0.010(2) 0.003(2) 0.011(2) C31 0.037(3) 0.018(2) 0.028(3) -0.005(2) 0.002(2) 0.011(2) C32 0.040(3) 0.028(3) 0.038(3) -0.005(3) -0.006(3) 0.010(3) C33 0.066(4) 0.034(3) 0.034(3) -0.002(3) 0.000(3) 0.016(3) C34 0.071(4) 0.028(3) 0.034(3) 0.002(3) 0.013(3) 0.001(3) C35 0.045(3) 0.037(3) 0.045(4) -0.004(3) 0.007(3) -0.007(3) C36 0.033(3) 0.031(3) 0.033(3) -0.006(2) 0.004(2) 0.000(2) C41 0.025(3) 0.027(3) 0.039(3) -0.005(2) -0.005(2) -0.003(2) C42 0.033(3) 0.028(3) 0.047(3) -0.003(3) 0.002(3) 0.001(3) C43 0.035(3) 0.043(4) 0.051(4) 0.001(3) 0.007(3) -0.008(3) C44 0.033(3) 0.049(4) 0.041(3) -0.005(3) 0.005(3) 0.004(3) C45 0.044(3) 0.029(3) 0.041(3) -0.009(3) -0.002(3) 0.010(3) C46 0.035(3) 0.027(3) 0.039(3) -0.003(2) 0.001(3) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O10 C10 1.222(5) . ? O14 C14 1.373(5) . ? O14 C17 1.433(5) . ? C1 C9 1.526(6) . ? C1 C31 1.527(6) . ? C1 C41 1.549(6) . ? C1 C2 1.561(6) . ? C2 C3 1.546(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.511(6) . ? C3 C10 1.526(6) . ? C3 H3 1.0000 . ? C4 C9 1.388(6) . ? C4 C5 1.397(6) . ? C5 C6 1.371(6) . ? C5 H5 0.9500 . ? C6 C7 1.391(6) . ? C6 H6 0.9500 . ? C7 C8 1.373(6) . ? C7 H7 0.9500 . ? C8 C9 1.396(6) . ? C8 H8 0.9500 . ? C10 C11 1.481(6) . ? C11 C16 1.382(5) . ? C11 C12 1.390(6) . ? C12 C13 1.386(6) . ? C12 H12 0.9500 . ? C13 C14 1.376(6) . ? C13 H13 0.9500 . ? C14 C15 1.381(6) . ? C15 C16 1.374(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C31 C32 1.391(6) . ? C31 C36 1.394(6) . ? C32 C33 1.389(7) . ? C32 H32 0.9500 . ? C33 C34 1.379(7) . ? C33 H33 0.9500 . ? C34 C35 1.392(7) . ? C34 H34 0.9500 . ? C35 C36 1.382(6) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C42 1.382(6) . ? C41 C46 1.392(6) . ? C42 C43 1.387(6) . ? C42 H42 0.9500 . ? C43 C44 1.370(7) . ? C43 H43 0.9500 . ? C44 C45 1.366(7) . ? C44 H44 0.9500 . ? C45 C46 1.398(6) . ? C45 H45 0.9500 . ? C46 H46 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 C14 O14 C17 117.0(3) . . ? C9 C1 C31 111.8(3) . . ? C9 C1 C41 109.9(4) . . ? C31 C1 C41 112.2(3) . . ? C9 C1 C2 100.5(3) . . ? C31 C1 C2 110.1(4) . . ? C41 C1 C2 111.7(4) . . ? C3 C2 C1 106.4(3) . . ? C3 C2 H2A 110.5 . . ? C1 C2 H2A 110.5 . . ? C3 C2 H2B 110.5 . . ? C1 C2 H2B 110.5 . . ? H2A C2 H2B 108.6 . . ? C4 C3 C10 111.3(3) . . ? C4 C3 C2 102.5(3) . . ? C10 C3 C2 112.5(3) . . ? C4 C3 H3 110.1 . . ? C10 C3 H3 110.1 . . ? C2 C3 H3 110.1 . . ? C9 C4 C5 120.2(4) . . ? C9 C4 C3 110.8(4) . . ? C5 C4 C3 128.9(4) . . ? C6 C5 C4 118.9(4) . . ? C6 C5 H5 120.5 . . ? C4 C5 H5 120.5 . . ? C5 C6 C7 120.9(4) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 120.7(4) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 119.0(4) . . ? C7 C8 H8 120.5 . . ? C9 C8 H8 120.5 . . ? C4 C9 C8 120.3(4) . . ? C4 C9 C1 111.6(4) . . ? C8 C9 C1 128.1(4) . . ? O10 C10 C11 119.7(4) . . ? O10 C10 C3 119.1(4) . . ? C11 C10 C3 121.2(4) . . ? C16 C11 C12 118.0(4) . . ? C16 C11 C10 117.8(4) . . ? C12 C11 C10 124.2(4) . . ? C13 C12 C11 121.0(4) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 C12 119.6(4) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? O14 C14 C13 125.2(4) . . ? O14 C14 C15 114.8(4) . . ? C13 C14 C15 120.0(4) . . ? C16 C15 C14 119.9(4) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C11 121.4(4) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? O14 C17 H17A 109.5 . . ? O14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C32 C31 C36 117.2(4) . . ? C32 C31 C1 119.4(4) . . ? C36 C31 C1 123.3(4) . . ? C33 C32 C31 121.9(5) . . ? C33 C32 H32 119.1 . . ? C31 C32 H32 119.1 . . ? C34 C33 C32 120.1(5) . . ? C34 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C33 C34 C35 118.9(5) . . ? C33 C34 H34 120.5 . . ? C35 C34 H34 120.5 . . ? C36 C35 C34 120.7(5) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C31 121.2(5) . . ? C35 C36 H36 119.4 . . ? C31 C36 H36 119.4 . . ? C42 C41 C46 117.9(4) . . ? C42 C41 C1 119.2(4) . . ? C46 C41 C1 122.9(4) . . ? C41 C42 C43 120.9(4) . . ? C41 C42 H42 119.5 . . ? C43 C42 H42 119.5 . . ? C44 C43 C42 120.8(5) . . ? C44 C43 H43 119.6 . . ? C42 C43 H43 119.6 . . ? C45 C44 C43 119.3(5) . . ? C45 C44 H44 120.3 . . ? C43 C44 H44 120.3 . . ? C44 C45 C46 120.5(4) . . ? C44 C45 H45 119.8 . . ? C46 C45 H45 119.8 . . ? C41 C46 C45 120.5(5) . . ? C41 C46 H46 119.7 . . ? C45 C46 H46 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 C9 C1 C2 C3 27.9(4) . . . . ? C31 C1 C2 C3 -90.2(4) . . . . ? C41 C1 C2 C3 144.4(4) . . . . ? C1 C2 C3 C4 -26.5(4) . . . . ? C1 C2 C3 C10 -146.2(4) . . . . ? C10 C3 C4 C9 135.1(4) . . . . ? C2 C3 C4 C9 14.6(5) . . . . ? C10 C3 C4 C5 -42.1(6) . . . . ? C2 C3 C4 C5 -162.6(4) . . . . ? C9 C4 C5 C6 -1.3(6) . . . . ? C3 C4 C5 C6 175.6(4) . . . . ? C4 C5 C6 C7 0.9(6) . . . . ? C5 C6 C7 C8 -0.3(7) . . . . ? C6 C7 C8 C9 0.2(6) . . . . ? C5 C4 C9 C8 1.2(6) . . . . ? C3 C4 C9 C8 -176.2(4) . . . . ? C5 C4 C9 C1 -179.1(4) . . . . ? C3 C4 C9 C1 3.5(5) . . . . ? C7 C8 C9 C4 -0.6(6) . . . . ? C7 C8 C9 C1 179.7(4) . . . . ? C31 C1 C9 C4 97.2(4) . . . . ? C41 C1 C9 C4 -137.5(4) . . . . ? C2 C1 C9 C4 -19.6(4) . . . . ? C31 C1 C9 C8 -83.1(5) . . . . ? C41 C1 C9 C8 42.2(6) . . . . ? C2 C1 C9 C8 160.1(4) . . . . ? C4 C3 C10 O10 -93.3(5) . . . . ? C2 C3 C10 O10 21.1(5) . . . . ? C4 C3 C10 C11 85.5(5) . . . . ? C2 C3 C10 C11 -160.2(4) . . . . ? O10 C10 C11 C16 7.6(6) . . . . ? C3 C10 C11 C16 -171.2(4) . . . . ? O10 C10 C11 C12 -172.1(4) . . . . ? C3 C10 C11 C12 9.2(6) . . . . ? C16 C11 C12 C13 -0.9(6) . . . . ? C10 C11 C12 C13 178.8(4) . . . . ? C11 C12 C13 C14 -0.1(6) . . . . ? C17 O14 C14 C13 10.3(6) . . . . ? C17 O14 C14 C15 -168.8(4) . . . . ? C12 C13 C14 O14 -178.6(4) . . . . ? C12 C13 C14 C15 0.4(6) . . . . ? O14 C14 C15 C16 179.3(4) . . . . ? C13 C14 C15 C16 0.2(6) . . . . ? C14 C15 C16 C11 -1.1(6) . . . . ? C12 C11 C16 C15 1.5(6) . . . . ? C10 C11 C16 C15 -178.2(4) . . . . ? C9 C1 C31 C32 -167.4(4) . . . . ? C41 C1 C31 C32 68.6(5) . . . . ? C2 C1 C31 C32 -56.5(5) . . . . ? C9 C1 C31 C36 11.9(6) . . . . ? C41 C1 C31 C36 -112.1(4) . . . . ? C2 C1 C31 C36 122.8(4) . . . . ? C36 C31 C32 C33 1.7(6) . . . . ? C1 C31 C32 C33 -179.0(4) . . . . ? C31 C32 C33 C34 -0.9(7) . . . . ? C32 C33 C34 C35 -0.5(7) . . . . ? C33 C34 C35 C36 1.0(7) . . . . ? C34 C35 C36 C31 -0.2(7) . . . . ? C32 C31 C36 C35 -1.1(6) . . . . ? C1 C31 C36 C35 179.6(4) . . . . ? C9 C1 C41 C42 54.9(5) . . . . ? C31 C1 C41 C42 -180.0(4) . . . . ? C2 C1 C41 C42 -55.7(5) . . . . ? C9 C1 C41 C46 -122.5(5) . . . . ? C31 C1 C41 C46 2.6(6) . . . . ? C2 C1 C41 C46 126.8(5) . . . . ? C46 C41 C42 C43 -1.4(7) . . . . ? C1 C41 C42 C43 -178.9(4) . . . . ? C41 C42 C43 C44 0.3(7) . . . . ? C42 C43 C44 C45 0.8(8) . . . . ? C43 C44 C45 C46 -0.7(7) . . . . ? C42 C41 C46 C45 1.5(7) . . . . ? C1 C41 C46 C45 178.9(4) . . . . ? C44 C45 C46 C41 -0.4(7) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.210 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.047 #======================================================================