# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email letizia.sambri@unibo.it _publ_contact_author_name 'Letizia Sambri' loop_ _publ_author_name 'Letizia Sambri' 'Andrea Baschieri' 'Mattia Boiani' 'Cristiana Cesari' 'Rita Mazzoni' 'Stefano Stagni' ; S.Zacchini ; data_c2c _database_code_depnum_ccdc_archive 'CCDC 862499' #TrackingRef '- C2C.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 O4' _chemical_formula_weight 374.42 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 Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.681(8) _cell_length_b 4.9756(18) _cell_length_c 33.914(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.726(5) _cell_angle_gamma 90.00 _cell_volume 3983(2) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3036 _cell_measurement_theta_min 2.4105 _cell_measurement_theta_max 25.330 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9817 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details ? _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 17291 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3419 _reflns_number_gt 2392 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1511P)^2^+16.9726P] 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 3419 _refine_ls_number_parameters 366 _refine_ls_number_restraints 622 _refine_ls_R_factor_all 0.1309 _refine_ls_R_factor_gt 0.0986 _refine_ls_wR_factor_ref 0.2948 _refine_ls_wR_factor_gt 0.2606 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.136 _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 0.2566(2) 0.2297(9) 0.37466(12) 0.0534(11) Uani 1 1 d DU . . O1 O 0.2980(3) 0.4317(18) 0.3604(2) 0.068(2) Uani 0.523(6) 1 d PDU A 1 H1 H 0.3027 0.5569 0.3769 0.101 Uiso 0.523(6) 1 calc PR A 1 C11 C 0.2304(4) 0.309(2) 0.4099(2) 0.051(2) Uani 0.523(6) 1 d PDU A 1 H11A H 0.2466 0.4805 0.4196 0.076 Uiso 0.523(6) 1 calc PR A 1 H11B H 0.2374 0.1712 0.4303 0.076 Uiso 0.523(6) 1 calc PR A 1 H11C H 0.1895 0.3298 0.4037 0.076 Uiso 0.523(6) 1 calc PR A 1 C12 C 0.3055(3) 0.0278(14) 0.39098(19) 0.0270(16) Uani 0.523(6) 1 d PDU A 1 H12A H 0.3260 -0.0373 0.3689 0.041 Uiso 0.523(6) 1 calc PR A 1 H12B H 0.2887 -0.1249 0.4040 0.041 Uiso 0.523(6) 1 calc PR A 1 H12C H 0.3319 0.1217 0.4100 0.041 Uiso 0.523(6) 1 calc PR A 1 C2 C 0.2238(2) 0.1035(10) 0.34085(12) 0.0440(10) Uani 1 1 d DU A . C3 C 0.19725(18) 0.0042(9) 0.31318(12) 0.0364(9) Uani 1 1 d DU . . C4 C 0.16591(16) -0.1273(8) 0.28070(11) 0.0327(9) Uani 1 1 d DU A . C5 C 0.19103(17) -0.3382(8) 0.26105(12) 0.0343(9) Uani 1 1 d DU . . H5 H 0.2285 -0.3936 0.2694 0.041 Uiso 1 1 calc R A . C6 C 0.16158(16) -0.4650(9) 0.22978(12) 0.0353(9) Uani 1 1 d DU A . H6 H 0.1792 -0.6054 0.2163 0.042 Uiso 1 1 calc R . . C7 C 0.10625(16) -0.3902(8) 0.21761(12) 0.0325(9) Uani 1 1 d DU . . C8 C 0.08092(17) -0.1798(8) 0.23772(11) 0.0328(9) Uani 1 1 d DU A . H8 H 0.0431 -0.1275 0.2298 0.039 Uiso 1 1 calc R . . C9 C 0.11043(17) -0.0497(9) 0.26864(12) 0.0357(9) Uani 1 1 d DU . . H9 H 0.0931 0.0930 0.2818 0.043 Uiso 1 1 calc R A . C10 C 0.07626(18) -0.5258(9) 0.18367(13) 0.0396(10) Uani 1 1 d DU A . O10 O 0.09963(14) -0.6664(8) 0.16083(12) 0.0638(11) Uani 1 1 d DU . . C21 C -0.1152(5) 0.441(2) -0.0113(3) 0.0547(17) Uani 0.465(5) 1 d PDU A 1 O21 O -0.1272(4) 0.2407(17) -0.0435(2) 0.064(2) Uani 0.465(5) 1 d PDU A 1 H21 H -0.1046 0.2641 -0.0610 0.095 Uiso 0.465(5) 1 calc PR A 1 C31 C -0.1709(5) 0.568(3) -0.0028(4) 0.061(3) Uani 0.465(5) 1 d PDU A 1 H31A H -0.1968 0.4292 0.0054 0.092 Uiso 0.465(5) 1 calc PR A 1 H31B H -0.1878 0.6575 -0.0267 0.092 Uiso 0.465(5) 1 calc PR A 1 H31C H -0.1643 0.7009 0.0185 0.092 Uiso 0.465(5) 1 calc PR A 1 C32 C -0.0764(5) 0.647(2) -0.0240(3) 0.059(3) Uani 0.465(5) 1 d PDU A 1 H32A H -0.0720 0.6252 -0.0523 0.089 Uiso 0.465(5) 1 calc PR A 1 H32B H -0.0395 0.6275 -0.0091 0.089 Uiso 0.465(5) 1 calc PR A 1 H32C H -0.0919 0.8253 -0.0193 0.089 Uiso 0.465(5) 1 calc PR A 1 C22 C -0.0892(5) 0.300(2) 0.0235(3) 0.0510(17) Uani 0.465(5) 1 d PDU A 1 C23 C -0.0718(5) 0.180(2) 0.0516(3) 0.0482(16) Uani 0.465(5) 1 d PDU A 1 C24 C -0.0495(3) 0.0147(16) 0.0837(2) 0.0452(15) Uani 0.465(5) 1 d PGDU A 1 C25 C -0.0873(3) -0.1047(19) 0.1077(3) 0.0425(16) Uani 0.465(5) 1 d PGDU A 1 H25 H -0.1268 -0.0713 0.1031 0.051 Uiso 0.465(5) 1 calc PR A 1 C26 C -0.0672(4) -0.2732(19) 0.1384(3) 0.0391(15) Uani 0.465(5) 1 d PGDU A 1 H26 H -0.0930 -0.3548 0.1548 0.047 Uiso 0.465(5) 1 calc PR A 1 C27 C -0.0095(4) -0.3221(18) 0.1452(3) 0.0392(14) Uani 0.465(5) 1 d PGDU A 1 C28 C 0.0283(3) -0.2027(19) 0.1212(3) 0.0459(16) Uani 0.465(5) 1 d PGDU A 1 H28 H 0.0678 -0.2362 0.1259 0.055 Uiso 0.465(5) 1 calc PR A 1 C29 C 0.0082(3) -0.0343(17) 0.0905(2) 0.0484(17) Uani 0.465(5) 1 d PGDU A 1 H29 H 0.0340 0.0473 0.0741 0.058 Uiso 0.465(5) 1 calc PR A 1 C30 C 0.01150(18) -0.4972(9) 0.17708(13) 0.0382(9) Uani 1 1 d DU . . O30 O -0.01581(12) -0.6368(8) 0.19784(9) 0.0491(9) Uani 1 1 d DU A . O1' O 0.2517(3) 0.0264(12) 0.40571(16) 0.0437(17) Uani 0.477(6) 1 d PDU A 2 H1' H 0.2835 0.0030 0.4181 0.066 Uiso 0.477(6) 1 calc PR A 2 C11' C 0.3143(4) 0.295(3) 0.3671(4) 0.058(3) Uani 0.477(6) 1 d PDU A 2 H11D H 0.3403 0.2232 0.3885 0.088 Uiso 0.477(6) 1 calc PR A 2 H11E H 0.3185 0.4909 0.3659 0.088 Uiso 0.477(6) 1 calc PR A 2 H11F H 0.3230 0.2159 0.3419 0.088 Uiso 0.477(6) 1 calc PR A 2 C12' C 0.2161(3) 0.4594(16) 0.3890(2) 0.0313(19) Uani 0.477(6) 1 d PDU A 2 H12D H 0.1792 0.3818 0.3937 0.047 Uiso 0.477(6) 1 calc PR A 2 H12E H 0.2111 0.5989 0.3687 0.047 Uiso 0.477(6) 1 calc PR A 2 H12F H 0.2332 0.5387 0.4137 0.047 Uiso 0.477(6) 1 calc PR A 2 C21' C -0.1527(5) 0.442(2) -0.0051(3) 0.0557(19) Uani 0.535(5) 1 d PDU A 2 O21' O -0.2010(3) 0.2746(14) -0.02275(19) 0.062(2) Uani 0.535(5) 1 d PDU A 2 H21' H -0.2072 0.3120 -0.0469 0.093 Uiso 0.535(5) 1 calc PR A 2 C31' C -0.1783(6) 0.700(2) 0.0080(3) 0.067(3) Uani 0.535(5) 1 d PDU A 2 H31D H -0.1979 0.7903 -0.0149 0.100 Uiso 0.535(5) 1 calc PR A 2 H31E H -0.1483 0.8173 0.0199 0.100 Uiso 0.535(5) 1 calc PR A 2 H31F H -0.2054 0.6612 0.0276 0.100 Uiso 0.535(5) 1 calc PR A 2 C32' C -0.1129(4) 0.483(2) -0.0376(3) 0.064(2) Uani 0.535(5) 1 d PDU A 2 H32D H -0.1329 0.5788 -0.0598 0.095 Uiso 0.535(5) 1 calc PR A 2 H32E H -0.1003 0.3073 -0.0467 0.095 Uiso 0.535(5) 1 calc PR A 2 H32F H -0.0800 0.5877 -0.0272 0.095 Uiso 0.535(5) 1 calc PR A 2 C22' C -0.1241(5) 0.296(2) 0.0287(3) 0.0522(15) Uani 0.535(5) 1 d PDU A 2 C23' C -0.1002(5) 0.177(2) 0.0562(3) 0.0490(15) Uani 0.535(5) 1 d PDU A 2 C24' C -0.0701(3) 0.0110(13) 0.0878(2) 0.0443(15) Uani 0.535(5) 1 d PGDU A 2 C25' C -0.1015(3) -0.1705(15) 0.1081(2) 0.0403(16) Uani 0.535(5) 1 d PGDU A 2 H25' H -0.1414 -0.1816 0.1024 0.048 Uiso 0.535(5) 1 calc PR A 2 C26' C -0.0746(4) -0.3358(15) 0.1369(3) 0.0386(15) Uani 0.535(5) 1 d PGDU A 2 H26' H -0.0961 -0.4598 0.1508 0.046 Uiso 0.535(5) 1 calc PR A 2 C27' C -0.0163(4) -0.3195(15) 0.1453(2) 0.0390(13) Uani 0.535(5) 1 d PGDU A 2 C28' C 0.0152(3) -0.1381(16) 0.1250(2) 0.0443(15) Uani 0.535(5) 1 d PGDU A 2 H28' H 0.0551 -0.1270 0.1307 0.053 Uiso 0.535(5) 1 calc PR A 2 C29' C -0.0117(3) 0.0272(14) 0.0962(2) 0.0483(16) Uani 0.535(5) 1 d PGDU A 2 H29' H 0.0098 0.1512 0.0823 0.058 Uiso 0.535(5) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.076(3) 0.048(2) 0.034(2) -0.0013(19) -0.005(2) 0.002(2) O1 0.052(4) 0.086(5) 0.062(4) -0.013(4) -0.010(3) 0.002(4) C11 0.057(4) 0.054(5) 0.040(4) 0.001(4) 0.001(4) -0.005(4) C12 0.028(3) 0.033(3) 0.019(3) 0.002(3) -0.007(3) -0.008(3) C2 0.060(2) 0.042(2) 0.031(2) 0.0024(18) 0.0069(18) 0.004(2) C3 0.042(2) 0.040(2) 0.0284(18) 0.0049(17) 0.0056(16) 0.0037(17) C4 0.0353(18) 0.0333(19) 0.0301(17) 0.0057(15) 0.0069(15) 0.0009(16) C5 0.0296(18) 0.035(2) 0.039(2) 0.0027(17) 0.0047(15) 0.0013(16) C6 0.0294(18) 0.034(2) 0.044(2) 0.0026(17) 0.0098(16) 0.0010(16) C7 0.0293(17) 0.0315(18) 0.0375(19) 0.0039(16) 0.0069(15) -0.0009(15) C8 0.0306(18) 0.036(2) 0.0327(18) 0.0057(16) 0.0086(15) 0.0022(16) C9 0.040(2) 0.036(2) 0.0325(19) 0.0020(16) 0.0110(16) 0.0058(17) C10 0.034(2) 0.037(2) 0.049(2) -0.0029(18) 0.0052(17) -0.0024(17) O10 0.0396(18) 0.071(2) 0.080(2) -0.039(2) 0.0025(17) 0.0058(17) C21 0.066(3) 0.053(3) 0.046(3) 0.007(3) 0.007(3) 0.012(3) O21 0.079(5) 0.060(4) 0.050(4) 0.003(4) -0.008(4) 0.009(4) C31 0.083(6) 0.057(6) 0.042(5) 0.010(5) -0.008(5) 0.014(6) C32 0.062(6) 0.058(6) 0.056(5) 0.002(5) -0.008(5) 0.017(5) C22 0.059(4) 0.050(3) 0.045(3) 0.009(3) 0.010(3) 0.010(3) C23 0.057(3) 0.044(3) 0.044(3) 0.008(3) 0.010(3) 0.006(3) C24 0.054(3) 0.039(3) 0.043(3) 0.007(2) 0.010(3) 0.002(3) C25 0.048(3) 0.040(3) 0.039(3) 0.004(3) 0.005(3) 0.001(3) C26 0.043(3) 0.038(3) 0.037(2) 0.003(3) 0.006(2) 0.002(3) C27 0.040(3) 0.036(2) 0.042(2) -0.001(2) 0.006(2) 0.002(2) C28 0.047(3) 0.038(3) 0.053(3) 0.006(3) 0.010(3) 0.003(3) C29 0.050(4) 0.042(3) 0.055(3) 0.007(3) 0.015(3) 0.004(3) C30 0.036(2) 0.038(2) 0.0404(19) -0.0013(17) 0.0032(16) -0.0034(17) O30 0.0344(16) 0.067(2) 0.0453(18) 0.0177(16) -0.0023(13) -0.0078(15) O1' 0.054(4) 0.044(3) 0.031(3) 0.007(3) -0.007(3) 0.000(3) C11' 0.064(5) 0.057(6) 0.053(5) 0.000(5) -0.006(4) 0.011(5) C12' 0.031(4) 0.039(4) 0.025(4) -0.005(3) 0.005(3) -0.006(3) C21' 0.071(4) 0.049(4) 0.047(3) 0.006(3) 0.004(3) 0.006(4) O21' 0.081(5) 0.055(4) 0.047(4) 0.009(3) -0.011(3) -0.016(4) C31' 0.104(6) 0.048(6) 0.045(5) 0.002(5) -0.009(5) 0.018(6) C32' 0.070(5) 0.065(5) 0.055(4) 0.009(4) -0.002(4) -0.007(4) C22' 0.062(3) 0.048(3) 0.047(3) 0.007(3) 0.010(3) 0.008(3) C23' 0.058(3) 0.044(3) 0.046(3) 0.006(2) 0.011(3) 0.006(3) C24' 0.053(3) 0.038(2) 0.043(2) 0.005(2) 0.011(3) 0.003(3) C25' 0.047(3) 0.037(3) 0.038(3) 0.005(3) 0.005(3) 0.002(3) C26' 0.042(3) 0.037(3) 0.037(2) 0.002(2) 0.006(2) 0.002(2) C27' 0.040(3) 0.036(2) 0.042(2) 0.000(2) 0.007(2) 0.002(2) C28' 0.044(3) 0.035(3) 0.055(3) 0.004(2) 0.012(3) 0.005(2) C29' 0.053(3) 0.039(3) 0.055(3) 0.010(2) 0.016(3) 0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C11' 1.447(8) . ? C1 C11 1.447(7) . ? C1 C2 1.471(6) . ? C1 O1' 1.472(6) . ? C1 O1 1.511(7) . ? C1 C12' 1.594(7) . ? C1 C12 1.598(6) . ? O1 H1 0.8400 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C2 C3 1.193(6) . ? C3 C4 1.434(6) . ? C4 C9 1.398(6) . ? C4 C5 1.402(6) . ? C5 C6 1.374(6) . ? C5 H5 0.9500 . ? C6 C7 1.392(5) . ? C6 H6 0.9500 . ? C7 C8 1.410(5) . ? C7 C10 1.466(6) . ? C8 C9 1.373(6) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 O10 1.211(5) . ? C10 C30 1.538(6) . ? C21 C22 1.462(12) . ? C21 C32 1.465(12) . ? C21 O21 1.487(11) . ? C21 C31 1.514(13) . ? O21 H21 0.8400 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C22 C23 1.171(11) . ? C23 C24 1.431(9) . ? C24 C25 1.3900 . ? C24 C29 1.3900 . ? C25 C26 1.3900 . ? C25 H25 0.9500 . ? C26 C27 1.3900 . ? C26 H26 0.9500 . ? C27 C28 1.3900 . ? C27 C30 1.444(7) . ? C28 C29 1.3900 . ? C28 H28 0.9500 . ? C29 H29 0.9500 . ? C30 O30 1.213(5) . ? C30 C27' 1.502(7) . ? O1' H1' 0.8400 . ? C11' H11D 0.9800 . ? C11' H11E 0.9800 . ? C11' H11F 0.9800 . ? C12' H12D 0.9800 . ? C12' H12E 0.9800 . ? C12' H12F 0.9800 . ? C21' C22' 1.474(12) . ? C21' O21' 1.498(11) . ? C21' C31' 1.504(11) . ? C21' C32' 1.522(12) . ? O21' H21' 0.8400 . ? C31' H31D 0.9800 . ? C31' H31E 0.9800 . ? C31' H31F 0.9800 . ? C32' H32D 0.9800 . ? C32' H32E 0.9800 . ? C32' H32F 0.9800 . ? C22' C23' 1.205(10) . ? C23' C24' 1.488(9) . ? C24' C25' 1.3900 . ? C24' C29' 1.3900 . ? C25' C26' 1.3900 . ? C25' H25' 0.9500 . ? C26' C27' 1.3900 . ? C26' H26' 0.9500 . ? C27' C28' 1.3900 . ? C28' C29' 1.3900 . ? C28' H28' 0.9500 . ? C29' H29' 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 C11' C1 C11 124.0(7) . . ? C11' C1 C2 113.8(6) . . ? C11 C1 C2 121.7(5) . . ? C11' C1 O1' 114.4(7) . . ? C11 C1 O1' 62.1(5) . . ? C2 C1 O1' 101.3(4) . . ? C11' C1 O1 31.5(5) . . ? C11 C1 O1 114.6(6) . . ? C2 C1 O1 110.4(4) . . ? O1' C1 O1 141.1(5) . . ? C11' C1 C12' 119.5(7) . . ? C11 C1 C12' 40.6(5) . . ? C2 C1 C12' 104.6(4) . . ? O1' C1 C12' 100.9(5) . . ? O1 C1 C12' 92.5(5) . . ? C11' C1 C12 62.3(6) . . ? C11 C1 C12 103.5(5) . . ? C2 C1 C12 108.9(4) . . ? O1' C1 C12 54.4(4) . . ? O1 C1 C12 93.4(5) . . ? C12' C1 C12 141.5(5) . . ? C1 O1 H1 109.5 . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C3 C2 C1 179.2(5) . . ? C2 C3 C4 177.4(5) . . ? C9 C4 C5 119.5(4) . . ? C9 C4 C3 120.9(4) . . ? C5 C4 C3 119.6(4) . . ? C6 C5 C4 120.2(4) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 120.8(4) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C6 C7 C8 118.9(4) . . ? C6 C7 C10 119.6(4) . . ? C8 C7 C10 121.6(4) . . ? C9 C8 C7 120.6(4) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C4 120.0(4) . . ? C8 C9 H9 120.0 . . ? C4 C9 H9 120.0 . . ? O10 C10 C7 123.4(4) . . ? O10 C10 C30 117.6(4) . . ? C7 C10 C30 118.9(4) . . ? C22 C21 C32 109.9(9) . . ? C22 C21 O21 108.4(8) . . ? C32 C21 O21 109.7(9) . . ? C22 C21 C31 111.2(9) . . ? C32 C21 C31 109.9(10) . . ? O21 C21 C31 107.7(10) . . ? C21 O21 H21 109.5 . . ? C21 C31 H31A 109.5 . . ? C21 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C21 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C21 C32 H32A 109.5 . . ? C21 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C21 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C23 C22 C21 175.6(13) . . ? C22 C23 C24 175.3(12) . . ? C25 C24 C29 120.0 . . ? C25 C24 C23 118.5(7) . . ? C29 C24 C23 121.5(7) . . ? C26 C25 C24 120.0 . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C25 C26 C27 120.0 . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C26 C27 C28 120.0 . . ? C26 C27 C30 120.2(6) . . ? C28 C27 C30 119.8(6) . . ? C29 C28 C27 120.0 . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? C28 C29 C24 120.0 . . ? C28 C29 H29 120.0 . . ? C24 C29 H29 120.0 . . ? O30 C30 C27 127.8(5) . . ? O30 C30 C27' 122.0(5) . . ? C27 C30 C27' 5.9(7) . . ? O30 C30 C10 115.8(4) . . ? C27 C30 C10 116.2(5) . . ? C27' C30 C10 122.1(5) . . ? C1 O1' H1' 109.5 . . ? C1 C11' H11D 109.5 . . ? C1 C11' H11E 109.5 . . ? H11D C11' H11E 109.5 . . ? C1 C11' H11F 109.5 . . ? H11D C11' H11F 109.5 . . ? H11E C11' H11F 109.5 . . ? C1 C12' H12D 109.5 . . ? C1 C12' H12E 109.5 . . ? H12D C12' H12E 109.5 . . ? C1 C12' H12F 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? C22' C21' O21' 108.9(8) . . ? C22' C21' C31' 111.3(8) . . ? O21' C21' C31' 106.3(9) . . ? C22' C21' C32' 110.8(9) . . ? O21' C21' C32' 106.4(8) . . ? C31' C21' C32' 112.9(9) . . ? C21' O21' H21' 109.5 . . ? C21' C31' H31D 109.5 . . ? C21' C31' H31E 109.5 . . ? H31D C31' H31E 109.5 . . ? C21' C31' H31F 109.5 . . ? H31D C31' H31F 109.5 . . ? H31E C31' H31F 109.5 . . ? C21' C32' H32D 109.5 . . ? C21' C32' H32E 109.5 . . ? H32D C32' H32E 109.5 . . ? C21' C32' H32F 109.5 . . ? H32D C32' H32F 109.5 . . ? H32E C32' H32F 109.5 . . ? C23' C22' C21' 179.4(12) . . ? C22' C23' C24' 175.1(10) . . ? C25' C24' C29' 120.0 . . ? C25' C24' C23' 118.2(6) . . ? C29' C24' C23' 121.7(6) . . ? C26' C25' C24' 120.0 . . ? C26' C25' H25' 120.0 . . ? C24' C25' H25' 120.0 . . ? C25' C26' C27' 120.0 . . ? C25' C26' H26' 120.0 . . ? C27' C26' H26' 120.0 . . ? C26' C27' C28' 120.0 . . ? C26' C27' C30 118.8(5) . . ? C28' C27' C30 121.2(5) . . ? C29' C28' C27' 120.0 . . ? C29' C28' H28' 120.0 . . ? C27' C28' H28' 120.0 . . ? C28' C29' C24' 120.0 . . ? C28' C29' H29' 120.0 . . ? C24' C29' H29' 120.0 . . ? 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 C11' C1 C2 C3 -65(37) . . . . ? C11 C1 C2 C3 108(37) . . . . ? O1' C1 C2 C3 172(100) . . . . ? O1 C1 C2 C3 -31(37) . . . . ? C12' C1 C2 C3 67(37) . . . . ? C12 C1 C2 C3 -132(37) . . . . ? C1 C2 C3 C4 162(100) . . . . ? C2 C3 C4 C9 128(10) . . . . ? C2 C3 C4 C5 -51(10) . . . . ? C9 C4 C5 C6 1.0(6) . . . . ? C3 C4 C5 C6 -179.7(4) . . . . ? C4 C5 C6 C7 -1.2(6) . . . . ? C5 C6 C7 C8 0.6(6) . . . . ? C5 C6 C7 C10 178.9(4) . . . . ? C6 C7 C8 C9 0.4(6) . . . . ? C10 C7 C8 C9 -177.9(4) . . . . ? C7 C8 C9 C4 -0.6(6) . . . . ? C5 C4 C9 C8 0.0(6) . . . . ? C3 C4 C9 C8 -179.4(4) . . . . ? C6 C7 C10 O10 -13.8(7) . . . . ? C8 C7 C10 O10 164.4(4) . . . . ? C6 C7 C10 C30 164.2(4) . . . . ? C8 C7 C10 C30 -17.6(6) . . . . ? C32 C21 C22 C23 173(16) . . . . ? O21 C21 C22 C23 -67(16) . . . . ? C31 C21 C22 C23 51(16) . . . . ? C21 C22 C23 C24 84(24) . . . . ? C22 C23 C24 C25 -104(16) . . . . ? C22 C23 C24 C29 74(16) . . . . ? C29 C24 C25 C26 0.0 . . . . ? C23 C24 C25 C26 178.0(9) . . . . ? C24 C25 C26 C27 0.0 . . . . ? C25 C26 C27 C28 0.0 . . . . ? C25 C26 C27 C30 -179.9(9) . . . . ? C26 C27 C28 C29 0.0 . . . . ? C30 C27 C28 C29 179.9(9) . . . . ? C27 C28 C29 C24 0.0 . . . . ? C25 C24 C29 C28 0.0 . . . . ? C23 C24 C29 C28 -177.9(9) . . . . ? C26 C27 C30 O30 8.1(10) . . . . ? C28 C27 C30 O30 -171.8(5) . . . . ? C26 C27 C30 C27' -3(7) . . . . ? C28 C27 C30 C27' 177(8) . . . . ? C26 C27 C30 C10 -176.6(5) . . . . ? C28 C27 C30 C10 3.4(9) . . . . ? O10 C10 C30 O30 99.5(5) . . . . ? C7 C10 C30 O30 -78.6(5) . . . . ? O10 C10 C30 C27 -76.3(7) . . . . ? C7 C10 C30 C27 105.6(7) . . . . ? O10 C10 C30 C27' -77.0(7) . . . . ? C7 C10 C30 C27' 104.9(6) . . . . ? O21' C21' C22' C23' 134(100) . . . . ? C31' C21' C22' C23' -109(100) . . . . ? C32' C21' C22' C23' 17(100) . . . . ? C21' C22' C23' C24' -78(100) . . . . ? C22' C23' C24' C25' -86(13) . . . . ? C22' C23' C24' C29' 91(13) . . . . ? C29' C24' C25' C26' 0.0 . . . . ? C23' C24' C25' C26' 177.8(7) . . . . ? C24' C25' C26' C27' 0.0 . . . . ? C25' C26' C27' C28' 0.0 . . . . ? C25' C26' C27' C30 178.9(7) . . . . ? O30 C30 C27' C26' -6.5(8) . . . . ? C27 C30 C27' C26' 164(8) . . . . ? C10 C30 C27' C26' 169.9(4) . . . . ? O30 C30 C27' C28' 172.4(5) . . . . ? C27 C30 C27' C28' -18(7) . . . . ? C10 C30 C27' C28' -11.2(8) . . . . ? C26' C27' C28' C29' 0.0 . . . . ? C30 C27' C28' C29' -178.9(7) . . . . ? C27' C28' C29' C24' 0.0 . . . . ? C25' C24' C29' C28' 0.0 . . . . ? C23' C24' C29' C28' -177.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.779 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.072 # Attachment '- P-1.CIF' data_p-1 _database_code_depnum_ccdc_archive 'CCDC 862500' #TrackingRef '- P-1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H32 O3' _chemical_formula_weight 548.65 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 6.0489(17) _cell_length_b 13.222(4) _cell_length_c 20.272(6) _cell_angle_alpha 73.883(4) _cell_angle_beta 86.839(4) _cell_angle_gamma 77.762(4) _cell_volume 1522.3(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1171 _cell_measurement_theta_min 2.278 _cell_measurement_theta_max 20.2285 _exptl_crystal_description plate _exptl_crystal_colour pale-red _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9897 _exptl_absorpt_correction_T_max 0.9926 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 11783 _diffrn_reflns_av_R_equivalents 0.1420 _diffrn_reflns_av_sigmaI/netI 0.1725 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 22.46 _reflns_number_total 3958 _reflns_number_gt 1592 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1862P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3958 _refine_ls_number_parameters 377 _refine_ls_number_restraints 321 _refine_ls_R_factor_all 0.2310 _refine_ls_R_factor_gt 0.1055 _refine_ls_wR_factor_ref 0.3554 _refine_ls_wR_factor_gt 0.2703 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.067 _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 1.2088(14) 0.8966(6) 0.0858(4) 0.0419(17) Uani 1 1 d U . . C2 C 1.3083(14) 0.7773(6) 0.0974(4) 0.0413(17) Uani 1 1 d U . . C3 C 1.1837(14) 0.7267(6) 0.1471(4) 0.0412(16) Uani 1 1 d U . . C4 C 1.0062(14) 0.8074(6) 0.1719(4) 0.0417(17) Uani 1 1 d U . . C5 C 1.0246(14) 0.9079(6) 0.1354(4) 0.0423(16) Uani 1 1 d U . . C6 C 1.2227(15) 0.6084(6) 0.1817(4) 0.0454(17) Uani 1 1 d U . . C7 C 1.4213(15) 0.5579(7) 0.2168(4) 0.0506(19) Uani 1 1 d U . . H7 H 1.5360 0.5952 0.2160 0.061 Uiso 1 1 calc R . . C8 C 1.4488(16) 0.4508(7) 0.2533(5) 0.054(2) Uani 1 1 d U . . H8 H 1.5828 0.4171 0.2775 0.065 Uiso 1 1 calc R . . C9 C 1.2851(16) 0.3925(7) 0.2549(4) 0.0498(18) Uani 1 1 d U . . C10 C 1.0921(16) 0.4424(7) 0.2171(5) 0.0520(19) Uani 1 1 d U . . H10 H 0.9821 0.4034 0.2158 0.062 Uiso 1 1 calc R . . C11 C 1.0582(15) 0.5499(6) 0.1807(4) 0.0503(19) Uani 1 1 d U . . H11 H 0.9256 0.5828 0.1557 0.060 Uiso 1 1 calc R . . C12 C 1.3171(16) 0.2834(7) 0.2972(5) 0.054(2) Uani 1 1 d U . . C13 C 1.3605(16) 0.1953(7) 0.3348(5) 0.058(2) Uani 1 1 d U A . C15 C 0.8538(15) 0.7779(6) 0.2301(4) 0.0436(17) Uani 1 1 d U . . C16 C 0.9332(16) 0.7038(7) 0.2908(4) 0.053(2) Uani 1 1 d U . . H16 H 1.0838 0.6680 0.2940 0.063 Uiso 1 1 calc R . . C17 C 0.7937(16) 0.6815(7) 0.3471(5) 0.057(2) Uani 1 1 d U . . H17 H 0.8515 0.6325 0.3879 0.068 Uiso 1 1 calc R . . C18 C 0.5662(16) 0.7327(7) 0.3426(5) 0.0560(19) Uani 1 1 d U . . C19 C 0.4851(16) 0.8023(7) 0.2817(5) 0.053(2) Uani 1 1 d U . . H19 H 0.3326 0.8352 0.2779 0.064 Uiso 1 1 calc R . . C20 C 0.6237(15) 0.8247(7) 0.2261(5) 0.0480(19) Uani 1 1 d U . . H20 H 0.5634 0.8720 0.1850 0.058 Uiso 1 1 calc R . . C21 C 0.4291(18) 0.7125(8) 0.4034(5) 0.069(2) Uani 1 1 d U . . C22 C 0.3222(19) 0.7015(9) 0.4550(6) 0.084(3) Uani 1 1 d U . . C24 C 1.5009(15) 0.7347(6) 0.0580(4) 0.0453(17) Uani 1 1 d U . . C25 C 1.5139(16) 0.6361(7) 0.0422(5) 0.0537(19) Uani 1 1 d U . . H25 H 1.3997 0.5974 0.0561 0.064 Uiso 1 1 calc R . . C26 C 1.6965(16) 0.5974(7) 0.0062(5) 0.059(2) Uani 1 1 d U . . H26 H 1.7072 0.5312 -0.0026 0.071 Uiso 1 1 calc R . . C27 C 1.8649(16) 0.6552(7) -0.0173(5) 0.060(2) Uani 1 1 d U . . H27 H 1.9868 0.6291 -0.0421 0.073 Uiso 1 1 calc R . . C28 C 1.8469(15) 0.7518(7) -0.0028(5) 0.053(2) Uani 1 1 d U . . H28 H 1.9584 0.7915 -0.0185 0.064 Uiso 1 1 calc R . . C29 C 1.6692(14) 0.7922(7) 0.0343(4) 0.0476(19) Uani 1 1 d U . . H29 H 1.6623 0.8579 0.0434 0.057 Uiso 1 1 calc R . . C30 C 0.9176(15) 1.0140(7) 0.1450(4) 0.0469(17) Uani 1 1 d U . . C31 C 1.0400(17) 1.0619(7) 0.1780(5) 0.062(2) Uani 1 1 d U . . H31 H 1.1857 1.0273 0.1935 0.074 Uiso 1 1 calc R . . C32 C 0.9471(18) 1.1620(7) 0.1883(5) 0.068(2) Uani 1 1 d U . . H32 H 1.0291 1.1927 0.2121 0.081 Uiso 1 1 calc R . . C33 C 0.7391(17) 1.2148(8) 0.1640(5) 0.066(2) Uani 1 1 d U . . H33 H 0.6811 1.2830 0.1694 0.080 Uiso 1 1 calc R . . C34 C 0.6139(17) 1.1687(7) 0.1317(5) 0.063(2) Uani 1 1 d U . . H34 H 0.4681 1.2040 0.1167 0.076 Uiso 1 1 calc R . . C35 C 0.7038(15) 1.0692(7) 0.1213(4) 0.052(2) Uani 1 1 d U . . H35 H 0.6191 1.0390 0.0979 0.062 Uiso 1 1 calc R . . O1 O 1.2703(10) 0.9696(4) 0.0423(3) 0.0601(18) Uani 1 1 d U . . C23 C 0.1976(19) 0.6919(10) 0.5203(6) 0.109(3) Uani 1 1 d DU . . O2 O 0.125(2) 0.7937(9) 0.5367(5) 0.168(4) Uani 1 1 d DU . . H2 H 0.2361 0.8180 0.5407 0.253 Uiso 1 1 calc R . . C36 C 0.345(2) 0.6136(12) 0.5774(6) 0.149(5) Uani 1 1 d DU . . H36A H 0.2646 0.6074 0.6201 0.224 Uiso 1 1 calc R . . H36B H 0.4805 0.6390 0.5804 0.224 Uiso 1 1 calc R . . H36C H 0.3838 0.5446 0.5683 0.224 Uiso 1 1 calc R . . C37 C -0.025(2) 0.6586(12) 0.5171(7) 0.141(5) Uani 1 1 d DU . . H37A H -0.1010 0.6538 0.5604 0.212 Uiso 1 1 calc R . . H37B H 0.0031 0.5898 0.5076 0.212 Uiso 1 1 calc R . . H37C H -0.1177 0.7110 0.4814 0.212 Uiso 1 1 calc R . . C14 C 1.4160(15) 0.0848(7) 0.3818(4) 0.063(2) Uani 1 1 d DU . . O3 O 1.560(2) 0.0906(10) 0.4343(6) 0.059(4) Uiso 0.477(12) 1 d PDU A 1 H3 H 1.5946 0.0313 0.4619 0.089 Uiso 0.477(12) 1 calc PR A 1 C38 C 1.592(3) 0.0228(15) 0.3410(10) 0.067(5) Uiso 0.477(12) 1 d PDU A 1 H38A H 1.6384 -0.0505 0.3677 0.101 Uiso 0.477(12) 1 calc PR A 1 H38B H 1.7214 0.0559 0.3314 0.101 Uiso 0.477(12) 1 calc PR A 1 H38C H 1.5258 0.0245 0.2987 0.101 Uiso 0.477(12) 1 calc PR A 1 C39 C 1.224(3) 0.0273(17) 0.4028(13) 0.073(5) Uiso 0.477(12) 1 d PDU A 1 H39A H 1.2798 -0.0426 0.4332 0.109 Uiso 0.477(12) 1 calc PR A 1 H39B H 1.1591 0.0197 0.3628 0.109 Uiso 0.477(12) 1 calc PR A 1 H39C H 1.1115 0.0679 0.4258 0.109 Uiso 0.477(12) 1 calc PR A 1 O4 O 1.350(2) 0.1004(10) 0.4504(5) 0.070(5) Uiso 0.523(12) 1 d PD A 2 H4 H 1.3751 0.0421 0.4795 0.106 Uiso 0.523(12) 1 calc PR A 2 C48 C 1.655(2) 0.0249(19) 0.3823(15) 0.127(11) Uiso 0.523(12) 1 d PD A 2 H48A H 1.6701 -0.0446 0.4149 0.190 Uiso 0.523(12) 1 calc PR A 2 H48B H 1.7535 0.0645 0.3950 0.190 Uiso 0.523(12) 1 calc PR A 2 H48C H 1.6941 0.0162 0.3374 0.190 Uiso 0.523(12) 1 calc PR A 2 C49 C 1.236(3) 0.0267(16) 0.3687(11) 0.076(7) Uiso 0.523(12) 1 d PD A 2 H49A H 1.2637 -0.0454 0.3983 0.113 Uiso 0.523(12) 1 calc PR A 2 H49B H 1.2437 0.0245 0.3216 0.113 Uiso 0.523(12) 1 calc PR A 2 H49C H 1.0892 0.0644 0.3778 0.113 Uiso 0.523(12) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.052(3) 0.028(3) 0.044(3) -0.009(3) 0.003(3) -0.007(3) C2 0.047(3) 0.029(3) 0.046(3) -0.010(3) 0.001(3) -0.005(3) C3 0.048(3) 0.029(3) 0.044(3) -0.007(3) -0.005(3) -0.007(3) C4 0.051(3) 0.034(3) 0.040(3) -0.009(3) -0.003(3) -0.007(3) C5 0.052(3) 0.032(3) 0.042(3) -0.013(3) -0.002(3) -0.005(3) C6 0.051(3) 0.034(3) 0.049(3) -0.004(3) -0.002(3) -0.010(3) C7 0.052(4) 0.040(3) 0.053(4) -0.002(3) -0.006(3) -0.008(3) C8 0.055(4) 0.043(4) 0.055(4) 0.000(3) -0.008(3) -0.007(3) C9 0.057(4) 0.036(3) 0.051(3) -0.003(3) -0.004(3) -0.009(3) C10 0.056(4) 0.036(3) 0.058(4) -0.002(3) -0.003(3) -0.013(3) C11 0.053(4) 0.038(3) 0.055(4) -0.002(3) -0.005(3) -0.010(3) C12 0.064(4) 0.040(4) 0.054(4) -0.002(3) -0.003(3) -0.011(3) C13 0.071(4) 0.042(4) 0.056(4) -0.003(3) -0.005(4) -0.013(4) C15 0.051(3) 0.036(3) 0.041(3) -0.005(3) 0.000(3) -0.009(3) C16 0.053(4) 0.047(4) 0.045(4) 0.003(3) 0.004(3) -0.003(3) C17 0.058(4) 0.053(4) 0.046(4) 0.006(3) 0.002(3) -0.007(3) C18 0.059(4) 0.057(4) 0.046(3) -0.002(3) 0.006(3) -0.016(3) C19 0.056(4) 0.051(4) 0.047(4) -0.004(3) 0.001(3) -0.013(3) C20 0.054(4) 0.041(4) 0.044(4) -0.001(3) -0.005(3) -0.012(3) C21 0.072(4) 0.073(4) 0.054(4) -0.003(4) 0.010(4) -0.020(4) C22 0.087(5) 0.097(5) 0.059(4) -0.007(4) 0.019(4) -0.023(4) C24 0.048(3) 0.032(3) 0.055(3) -0.014(3) 0.001(3) -0.003(3) C25 0.056(4) 0.040(4) 0.064(4) -0.017(3) 0.000(3) -0.003(3) C26 0.058(4) 0.046(4) 0.067(4) -0.018(3) 0.002(4) 0.002(3) C27 0.056(4) 0.053(4) 0.065(4) -0.014(4) 0.006(4) 0.003(3) C28 0.050(4) 0.046(4) 0.059(4) -0.009(3) 0.005(3) -0.005(3) C29 0.049(4) 0.035(3) 0.056(4) -0.012(3) 0.002(3) -0.006(3) C30 0.053(3) 0.037(3) 0.051(3) -0.016(3) -0.005(3) -0.003(3) C31 0.067(4) 0.045(4) 0.071(4) -0.019(3) -0.013(4) 0.001(3) C32 0.076(4) 0.050(4) 0.079(4) -0.026(4) -0.013(4) -0.001(4) C33 0.071(5) 0.047(4) 0.075(4) -0.020(4) -0.005(4) 0.007(4) C34 0.064(4) 0.047(4) 0.068(4) -0.013(4) -0.004(4) 0.009(4) C35 0.055(4) 0.039(4) 0.057(4) -0.013(3) -0.008(3) 0.001(3) O1 0.068(4) 0.035(3) 0.067(4) -0.003(3) 0.018(3) -0.008(3) C23 0.111(6) 0.127(6) 0.076(5) -0.008(5) 0.025(5) -0.027(5) O2 0.189(8) 0.159(8) 0.143(7) -0.033(6) 0.046(7) -0.026(7) C36 0.137(9) 0.191(10) 0.079(8) 0.014(8) 0.017(7) -0.016(9) C37 0.117(9) 0.198(10) 0.094(8) -0.006(8) 0.022(7) -0.051(8) C14 0.079(4) 0.051(4) 0.058(4) -0.010(3) -0.010(4) -0.016(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.221(9) . ? C1 C5 1.471(11) . ? C1 C2 1.520(10) . ? C2 C3 1.337(10) . ? C2 C24 1.477(11) . ? C3 C6 1.499(11) . ? C3 C4 1.516(11) . ? C4 C5 1.354(10) . ? C4 C15 1.474(11) . ? C5 C30 1.476(11) . ? C6 C7 1.373(11) . ? C6 C11 1.389(11) . ? C7 C8 1.383(11) . ? C7 H7 0.9300 . ? C8 C9 1.371(12) . ? C8 H8 0.9300 . ? C9 C10 1.371(12) . ? C9 C12 1.438(11) . ? C10 C11 1.384(11) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.186(11) . ? C13 C14 1.487(12) . ? C15 C16 1.379(11) . ? C15 C20 1.395(11) . ? C16 C17 1.383(11) . ? C16 H16 0.9300 . ? C17 C18 1.394(12) . ? C17 H17 0.9300 . ? C18 C19 1.361(12) . ? C18 C21 1.443(13) . ? C19 C20 1.371(11) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.189(12) . ? C22 C23 1.474(15) . ? C24 C29 1.384(11) . ? C24 C25 1.413(11) . ? C25 C26 1.377(12) . ? C25 H25 0.9300 . ? C26 C27 1.387(12) . ? C26 H26 0.9300 . ? C27 C28 1.369(12) . ? C27 H27 0.9300 . ? C28 C29 1.377(11) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? C30 C31 1.372(12) . ? C30 C35 1.382(12) . ? C31 C32 1.391(12) . ? C31 H31 0.9300 . ? C32 C33 1.348(12) . ? C32 H32 0.9300 . ? C33 C34 1.358(13) . ? C33 H33 0.9300 . ? C34 C35 1.381(11) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C23 O2 1.449(8) . ? C23 C36 1.505(8) . ? C23 C37 1.511(8) . ? O2 H2 0.8200 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C14 O3 1.441(8) . ? C14 O4 1.484(8) . ? C14 C48 1.491(9) . ? C14 C39 1.497(9) . ? C14 C49 1.530(8) . ? C14 C38 1.549(8) . ? O3 H3 0.8200 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? O4 H4 0.8200 . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C5 126.4(7) . . ? O1 C1 C2 125.6(8) . . ? C5 C1 C2 108.0(7) . . ? C3 C2 C24 130.9(7) . . ? C3 C2 C1 105.6(7) . . ? C24 C2 C1 123.6(7) . . ? C2 C3 C6 127.1(8) . . ? C2 C3 C4 110.4(7) . . ? C6 C3 C4 122.1(7) . . ? C5 C4 C15 127.1(7) . . ? C5 C4 C3 108.9(7) . . ? C15 C4 C3 123.9(7) . . ? C4 C5 C1 107.1(7) . . ? C4 C5 C30 131.0(8) . . ? C1 C5 C30 121.3(7) . . ? C7 C6 C11 119.5(8) . . ? C7 C6 C3 119.5(8) . . ? C11 C6 C3 121.0(8) . . ? C6 C7 C8 119.2(9) . . ? C6 C7 H7 120.4 . . ? C8 C7 H7 120.4 . . ? C9 C8 C7 122.2(9) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C10 C9 C8 118.1(8) . . ? C10 C9 C12 122.2(9) . . ? C8 C9 C12 119.7(9) . . ? C9 C10 C11 121.1(9) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? C10 C11 C6 119.8(9) . . ? C10 C11 H11 120.1 . . ? C6 C11 H11 120.1 . . ? C13 C12 C9 173.7(11) . . ? C12 C13 C14 179.8(12) . . ? C16 C15 C20 117.4(8) . . ? C16 C15 C4 121.4(8) . . ? C20 C15 C4 121.2(7) . . ? C15 C16 C17 121.4(9) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C16 C17 C18 119.9(8) . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C19 C18 C17 118.8(9) . . ? C19 C18 C21 122.9(9) . . ? C17 C18 C21 118.3(8) . . ? C18 C19 C20 121.3(9) . . ? C18 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C19 C20 C15 121.1(8) . . ? C19 C20 H20 119.5 . . ? C15 C20 H20 119.5 . . ? C22 C21 C18 175.1(12) . . ? C21 C22 C23 176.5(14) . . ? C29 C24 C25 118.7(8) . . ? C29 C24 C2 120.6(8) . . ? C25 C24 C2 120.7(8) . . ? C26 C25 C24 119.6(9) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C27 121.4(9) . . ? C25 C26 H26 119.3 . . ? C27 C26 H26 119.3 . . ? C28 C27 C26 118.2(9) . . ? C28 C27 H27 120.9 . . ? C26 C27 H27 120.9 . . ? C27 C28 C29 122.2(9) . . ? C27 C28 H28 118.9 . . ? C29 C28 H28 118.9 . . ? C28 C29 C24 120.0(8) . . ? C28 C29 H29 120.0 . . ? C24 C29 H29 120.0 . . ? C31 C30 C35 118.1(8) . . ? C31 C30 C5 118.0(8) . . ? C35 C30 C5 123.9(8) . . ? C30 C31 C32 120.3(9) . . ? C30 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C33 C32 C31 120.5(10) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C34 120.2(9) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C33 C34 C35 119.8(10) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C34 C35 C30 121.0(9) . . ? C34 C35 H35 119.5 . . ? C30 C35 H35 119.5 . . ? O2 C23 C22 113.0(10) . . ? O2 C23 C36 109.3(11) . . ? C22 C23 C36 109.2(10) . . ? O2 C23 C37 102.0(10) . . ? C22 C23 C37 112.0(11) . . ? C36 C23 C37 111.1(11) . . ? C23 O2 H2 109.5 . . ? C23 C36 H36A 109.5 . . ? C23 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C23 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C23 C37 H37A 109.5 . . ? C23 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C23 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O3 C14 O4 52.1(6) . . ? O3 C14 C13 105.8(8) . . ? O4 C14 C13 103.7(8) . . ? O3 C14 C48 64.1(11) . . ? O4 C14 C48 110.9(12) . . ? C13 C14 C48 117.1(13) . . ? O3 C14 C39 118.8(12) . . ? O4 C14 C39 75.8(11) . . ? C13 C14 C39 116.9(12) . . ? C48 C14 C39 121.5(16) . . ? O3 C14 C49 143.0(12) . . ? O4 C14 C49 101.8(10) . . ? C13 C14 C49 106.0(11) . . ? C48 C14 C49 115.5(13) . . ? C39 C14 C49 26.5(11) . . ? O3 C14 C38 99.9(10) . . ? O4 C14 C38 145.5(11) . . ? C13 C14 C38 103.5(10) . . ? C48 C14 C38 36.3(11) . . ? C39 C14 C38 109.6(12) . . ? C49 C14 C38 90.5(12) . . ? C14 O3 H3 109.5 . . ? C14 C38 H38A 109.5 . . ? C14 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C14 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C14 C39 H39A 109.5 . . ? C14 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C14 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C14 O4 H4 109.5 . . ? C14 C48 H48A 109.5 . . ? C14 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C14 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C14 C49 H49A 109.5 . . ? C14 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C14 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 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 O1 C1 C2 C3 -176.8(9) . . . . ? C5 C1 C2 C3 2.4(10) . . . . ? O1 C1 C2 C24 2.2(14) . . . . ? C5 C1 C2 C24 -178.6(8) . . . . ? C24 C2 C3 C6 6.4(16) . . . . ? C1 C2 C3 C6 -174.7(8) . . . . ? C24 C2 C3 C4 179.1(9) . . . . ? C1 C2 C3 C4 -2.0(9) . . . . ? C2 C3 C4 C5 0.8(10) . . . . ? C6 C3 C4 C5 174.0(8) . . . . ? C2 C3 C4 C15 -174.8(8) . . . . ? C6 C3 C4 C15 -1.7(13) . . . . ? C15 C4 C5 C1 176.3(8) . . . . ? C3 C4 C5 C1 0.8(10) . . . . ? C15 C4 C5 C30 5.3(16) . . . . ? C3 C4 C5 C30 -170.2(9) . . . . ? O1 C1 C5 C4 177.3(9) . . . . ? C2 C1 C5 C4 -2.0(10) . . . . ? O1 C1 C5 C30 -10.7(14) . . . . ? C2 C1 C5 C30 170.0(8) . . . . ? C2 C3 C6 C7 60.2(13) . . . . ? C4 C3 C6 C7 -111.8(10) . . . . ? C2 C3 C6 C11 -121.8(10) . . . . ? C4 C3 C6 C11 66.2(11) . . . . ? C11 C6 C7 C8 -3.2(13) . . . . ? C3 C6 C7 C8 174.8(8) . . . . ? C6 C7 C8 C9 0.9(14) . . . . ? C7 C8 C9 C10 2.2(14) . . . . ? C7 C8 C9 C12 -176.1(8) . . . . ? C8 C9 C10 C11 -3.0(14) . . . . ? C12 C9 C10 C11 175.3(8) . . . . ? C9 C10 C11 C6 0.7(14) . . . . ? C7 C6 C11 C10 2.4(13) . . . . ? C3 C6 C11 C10 -175.5(8) . . . . ? C10 C9 C12 C13 -167(9) . . . . ? C8 C9 C12 C13 11(10) . . . . ? C9 C12 C13 C14 -52(100) . . . . ? C5 C4 C15 C16 -130.0(10) . . . . ? C3 C4 C15 C16 44.9(12) . . . . ? C5 C4 C15 C20 49.4(13) . . . . ? C3 C4 C15 C20 -135.8(9) . . . . ? C20 C15 C16 C17 -3.9(14) . . . . ? C4 C15 C16 C17 175.5(8) . . . . ? C15 C16 C17 C18 1.5(14) . . . . ? C16 C17 C18 C19 1.5(15) . . . . ? C16 C17 C18 C21 -176.3(9) . . . . ? C17 C18 C19 C20 -1.8(14) . . . . ? C21 C18 C19 C20 175.8(9) . . . . ? C18 C19 C20 C15 -0.7(14) . . . . ? C16 C15 C20 C19 3.6(13) . . . . ? C4 C15 C20 C19 -175.8(8) . . . . ? C19 C18 C21 C22 -95(14) . . . . ? C17 C18 C21 C22 83(14) . . . . ? C18 C21 C22 C23 -11(32) . . . . ? C3 C2 C24 C29 -149.0(10) . . . . ? C1 C2 C24 C29 32.3(13) . . . . ? C3 C2 C24 C25 32.8(15) . . . . ? C1 C2 C24 C25 -146.0(8) . . . . ? C29 C24 C25 C26 2.5(13) . . . . ? C2 C24 C25 C26 -179.2(8) . . . . ? C24 C25 C26 C27 -2.3(14) . . . . ? C25 C26 C27 C28 0.9(14) . . . . ? C26 C27 C28 C29 0.4(14) . . . . ? C27 C28 C29 C24 -0.2(14) . . . . ? C25 C24 C29 C28 -1.2(13) . . . . ? C2 C24 C29 C28 -179.5(8) . . . . ? C4 C5 C30 C31 97.9(12) . . . . ? C1 C5 C30 C31 -71.9(11) . . . . ? C4 C5 C30 C35 -83.8(13) . . . . ? C1 C5 C30 C35 106.3(11) . . . . ? C35 C30 C31 C32 1.5(14) . . . . ? C5 C30 C31 C32 179.9(8) . . . . ? C30 C31 C32 C33 -2.3(15) . . . . ? C31 C32 C33 C34 2.8(16) . . . . ? C32 C33 C34 C35 -2.6(15) . . . . ? C33 C34 C35 C30 1.9(14) . . . . ? C31 C30 C35 C34 -1.4(14) . . . . ? C5 C30 C35 C34 -179.6(8) . . . . ? C21 C22 C23 O2 46(21) . . . . ? C21 C22 C23 C36 -76(21) . . . . ? C21 C22 C23 C37 161(20) . . . . ? C12 C13 C14 O3 69(100) . . . . ? C12 C13 C14 O4 123(100) . . . . ? C12 C13 C14 C48 1(100) . . . . ? C12 C13 C14 C39 -156(100) . . . . ? C12 C13 C14 C49 -130(100) . . . . ? C12 C13 C14 C38 -35(100) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O3 0.82 2.07 2.858(16) 161.6 2_766 O3 H3 O3 0.82 2.54 3.22(3) 141.1 2_856 O4 H4 O4 0.82 2.41 3.13(2) 147.6 2_856 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 22.46 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.614 _refine_diff_density_min -0.577 _refine_diff_density_rms 0.070