# Electronic Supplementary Material (ESI) for Polymer Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Polym.Chem. _journal_coden_Cambridge 1478 _publ_contact_author_name 'Rongrong Hu' _publ_contact_author_address ; ; _publ_contact_author_email tangbenz@ust.hk loop_ _publ_author_name 'Rongrong Hu' 'Jacky W. Y. Lam' 'Yong Yu' 'Herman H. Y. Sung' 'Ian D. Williams' 'Matthew M. F. Yuen' ; B.Z.Tang ; # Attachment '- 1.cif' data_rong4 _database_code_depnum_ccdc_archive 'CCDC 885935' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 O4' _chemical_formula_weight 472.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 '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 8.9570(2) _cell_length_b 11.1473(3) _cell_length_c 12.7782(4) _cell_angle_alpha 80.558(2) _cell_angle_beta 89.540(2) _cell_angle_gamma 86.557(2) _cell_volume 1256.30(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8712 _cell_measurement_theta_min 3.50 _cell_measurement_theta_max 71.28 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.654 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11051 _diffrn_reflns_av_R_equivalents 0.0371 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 67.46 _reflns_number_total 4445 _reflns_number_gt 3910 _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^)+(0.0550P)^2^+0.1685P] 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 4445 _refine_ls_number_parameters 345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.06303(11) 0.29388(9) 0.49873(7) 0.0552(3) Uani 1 1 d . . . O2 O -0.14879(13) 0.13568(11) 0.43398(9) 0.0715(3) Uani 1 1 d . . . O3 O 0.7353(3) 0.7821(2) 0.30523(17) 0.0485(5) Uani 0.70 1 d P A 1 O4 O 0.9597(3) 0.7305(3) 0.24058(19) 0.0738(7) Uani 0.70 1 d P A 1 O3A O 0.7769(9) 0.7772(7) 0.2926(5) 0.0552(17) Uiso 0.30 1 d P A 2 O4A O 0.9883(6) 0.6781(5) 0.2485(4) 0.0665(16) Uiso 0.30 1 d P A 2 C1 C 0.32513(13) 0.33152(10) 0.31385(9) 0.0381(3) Uani 1 1 d . . . C2 C 0.29336(14) 0.21766(11) 0.37041(9) 0.0426(3) Uani 1 1 d . . . H2A H 0.3617 0.1497 0.3677 0.051 Uiso 1 1 calc R . . C3 C 0.16422(15) 0.20166(11) 0.43044(10) 0.0455(3) Uani 1 1 d . . . H3A H 0.1446 0.1239 0.4690 0.055 Uiso 1 1 calc R . . C4 C 0.06442(14) 0.30072(12) 0.43333(9) 0.0436(3) Uani 1 1 d . . . C5 C 0.09144(14) 0.41451(11) 0.37851(10) 0.0440(3) Uani 1 1 d . . . H5A H 0.0217 0.4817 0.3807 0.053 Uiso 1 1 calc R . . C6 C 0.22220(14) 0.42939(11) 0.32002(9) 0.0412(3) Uani 1 1 d . . . H6A H 0.2422 0.5080 0.2833 0.049 Uiso 1 1 calc R . . C7 C -0.16175(16) 0.20802(12) 0.49307(11) 0.0503(3) Uani 1 1 d . . . C8 C -0.28775(19) 0.21840(15) 0.56679(13) 0.0639(4) Uani 1 1 d . . . H8A H -0.2881 0.2777 0.6124 0.077 Uiso 1 1 calc R . . C9 C -0.39838(19) 0.14743(16) 0.57010(16) 0.0745(5) Uani 1 1 d . . . H9A H -0.3987 0.0880 0.5247 0.089 Uiso 1 1 calc R . . H9B H -0.4788 0.1551 0.6179 0.089 Uiso 1 1 calc R . . C10 C 0.46604(13) 0.35127(10) 0.25194(9) 0.0380(3) Uani 1 1 d . . . C11 C 0.54219(13) 0.46354(10) 0.26544(9) 0.0377(3) Uani 1 1 d . A . C12 C 0.57972(14) 0.48604(11) 0.36570(9) 0.0431(3) Uani 1 1 d . . . H12A H 0.5553 0.4297 0.4266 0.052 Uiso 1 1 calc R . . C13 C 0.65213(15) 0.58930(12) 0.37803(10) 0.0473(3) Uani 1 1 d . A . H13A H 0.6790 0.6032 0.4466 0.057 Uiso 1 1 calc R . . C14 C 0.68449(14) 0.67153(11) 0.28908(10) 0.0447(3) Uani 1 1 d . . . C15 C 0.64698(15) 0.65291(11) 0.18868(10) 0.0444(3) Uani 1 1 d . A . H15A H 0.6696 0.7106 0.1282 0.053 Uiso 1 1 calc R . . C16 C 0.57607(14) 0.54898(11) 0.17755(9) 0.0416(3) Uani 1 1 d . . . H16A H 0.5500 0.5356 0.1087 0.050 Uiso 1 1 calc R A . C17 C 0.8787(4) 0.8046(3) 0.27413(15) 0.0445(5) Uani 0.70 1 d P A 1 C18 C 0.9098(3) 0.9275(2) 0.29128(16) 0.0533(5) Uani 0.70 1 d P A 1 H18A H 0.8348 0.9755 0.3211 0.064 Uiso 0.70 1 calc PR A 1 C19 C 1.0393(4) 0.9720(3) 0.2660(2) 0.0766(7) Uani 0.70 1 d P A 1 H19A H 1.1148 0.9245 0.2361 0.092 Uiso 0.70 1 calc PR A 1 H19B H 1.0580 1.0518 0.2775 0.092 Uiso 0.70 1 calc PR A 1 C17A C 0.9286(11) 0.7658(8) 0.2665(7) 0.0489(19) Uiso 0.30 1 d P A 2 C18A C 0.9938(7) 0.8878(5) 0.2600(4) 0.0566(11) Uiso 0.30 1 d P A 2 H18B H 1.0980 0.8912 0.2463 0.068 Uiso 0.30 1 calc PR A 2 C19A C 0.9220(9) 0.9878(7) 0.2713(5) 0.0676(17) Uiso 0.30 1 d P A 2 H19C H 0.8176 0.9889 0.2851 0.081 Uiso 0.30 1 calc PR A 2 H19D H 0.9732 1.0608 0.2658 0.081 Uiso 0.30 1 calc PR A 2 C20 C 0.52092(13) 0.27711(10) 0.18481(9) 0.0384(3) Uani 1 1 d . . . C21 C 0.66729(13) 0.29542(10) 0.12900(9) 0.0386(3) Uani 1 1 d . . . C22 C 0.67536(14) 0.29499(11) 0.02005(9) 0.0423(3) Uani 1 1 d . . . H22A H 0.5900 0.2760 -0.0163 0.051 Uiso 1 1 calc R . . C23 C 0.80521(15) 0.32167(12) -0.03631(10) 0.0484(3) Uani 1 1 d . . . H23A H 0.8080 0.3220 -0.1107 0.058 Uiso 1 1 calc R . . C24 C 0.93074(16) 0.34782(13) 0.01588(12) 0.0539(3) Uani 1 1 d . . . H24A H 1.0194 0.3683 -0.0226 0.065 Uiso 1 1 calc R . . C25 C 0.92633(16) 0.34394(15) 0.12462(12) 0.0586(4) Uani 1 1 d . . . H25A H 1.0133 0.3597 0.1610 0.070 Uiso 1 1 calc R . . C26 C 0.79674(15) 0.31739(13) 0.18078(10) 0.0495(3) Uani 1 1 d . . . H26A H 0.7959 0.3141 0.2555 0.059 Uiso 1 1 calc R . . C31 C 0.43484(14) 0.17875(11) 0.15190(9) 0.0399(3) Uani 1 1 d . . . C32 C 0.49481(17) 0.05921(12) 0.16388(12) 0.0533(3) Uani 1 1 d . . . H32A H 0.5880 0.0381 0.1991 0.064 Uiso 1 1 calc R . . C33 C 0.41996(19) -0.02913(13) 0.12502(14) 0.0633(4) Uani 1 1 d . . . H33A H 0.4610 -0.1108 0.1352 0.076 Uiso 1 1 calc R . . C34 C 0.28639(18) 0.00034(13) 0.07168(13) 0.0613(4) Uani 1 1 d . . . H34A H 0.2366 -0.0603 0.0436 0.074 Uiso 1 1 calc R . . C35 C 0.22552(16) 0.11818(13) 0.05935(12) 0.0555(3) Uani 1 1 d . . . H35A H 0.1329 0.1388 0.0232 0.067 Uiso 1 1 calc R . . C36 C 0.29908(14) 0.20694(12) 0.09964(10) 0.0455(3) Uani 1 1 d . . . H36A H 0.2559 0.2879 0.0913 0.055 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0560(6) 0.0582(5) 0.0565(5) -0.0213(4) 0.0198(4) -0.0155(4) O2 0.0624(7) 0.0855(8) 0.0775(7) -0.0380(6) 0.0153(6) -0.0265(6) O3 0.0444(12) 0.0468(9) 0.0622(11) -0.0276(7) 0.0086(9) -0.0167(8) O4 0.0544(12) 0.0803(18) 0.0986(16) -0.0444(14) 0.0304(10) -0.0241(12) C1 0.0388(6) 0.0419(6) 0.0361(5) -0.0128(5) -0.0015(5) -0.0060(5) C2 0.0446(7) 0.0415(6) 0.0431(6) -0.0108(5) 0.0000(5) -0.0028(5) C3 0.0515(7) 0.0441(6) 0.0421(6) -0.0079(5) 0.0041(5) -0.0100(6) C4 0.0441(7) 0.0515(7) 0.0389(6) -0.0161(5) 0.0057(5) -0.0104(5) C5 0.0435(7) 0.0458(6) 0.0458(6) -0.0169(5) 0.0021(5) -0.0025(5) C6 0.0430(7) 0.0402(6) 0.0422(6) -0.0113(5) 0.0015(5) -0.0060(5) C7 0.0497(8) 0.0527(7) 0.0486(7) -0.0073(6) 0.0043(6) -0.0072(6) C8 0.0604(9) 0.0641(9) 0.0666(9) -0.0085(7) 0.0201(7) -0.0071(7) C9 0.0546(9) 0.0697(10) 0.0931(12) 0.0031(9) 0.0199(9) -0.0027(8) C10 0.0373(6) 0.0408(6) 0.0370(6) -0.0093(5) -0.0022(5) -0.0031(5) C11 0.0336(6) 0.0421(6) 0.0397(6) -0.0133(5) 0.0013(4) -0.0026(5) C12 0.0469(7) 0.0490(7) 0.0356(6) -0.0115(5) 0.0024(5) -0.0079(5) C13 0.0528(7) 0.0549(7) 0.0389(6) -0.0194(5) -0.0019(5) -0.0087(6) C14 0.0444(7) 0.0426(6) 0.0512(7) -0.0181(5) 0.0016(5) -0.0073(5) C15 0.0494(7) 0.0423(6) 0.0427(6) -0.0092(5) 0.0025(5) -0.0053(5) C16 0.0450(7) 0.0445(6) 0.0374(6) -0.0124(5) -0.0021(5) -0.0039(5) C17 0.0440(14) 0.0514(13) 0.0413(11) -0.0141(9) 0.0073(9) -0.0130(12) C18 0.0608(14) 0.0528(13) 0.0484(11) -0.0102(10) 0.0016(9) -0.0161(11) C19 0.087(2) 0.0722(15) 0.0769(16) -0.0187(12) 0.0144(13) -0.0386(14) C20 0.0369(6) 0.0400(6) 0.0388(6) -0.0087(5) -0.0020(5) -0.0015(5) C21 0.0378(6) 0.0378(6) 0.0416(6) -0.0110(5) -0.0013(5) 0.0002(5) C22 0.0432(7) 0.0426(6) 0.0429(6) -0.0124(5) -0.0030(5) -0.0027(5) C23 0.0527(8) 0.0493(7) 0.0437(6) -0.0089(5) 0.0055(6) -0.0040(6) C24 0.0426(7) 0.0584(8) 0.0630(8) -0.0158(6) 0.0108(6) -0.0077(6) C25 0.0375(7) 0.0791(10) 0.0648(9) -0.0276(7) -0.0024(6) -0.0067(6) C26 0.0407(7) 0.0661(8) 0.0447(7) -0.0188(6) -0.0031(5) 0.0002(6) C31 0.0399(6) 0.0409(6) 0.0409(6) -0.0123(5) 0.0055(5) -0.0044(5) C32 0.0511(8) 0.0450(7) 0.0645(8) -0.0130(6) 0.0016(6) 0.0017(6) C33 0.0674(10) 0.0395(7) 0.0865(11) -0.0209(7) 0.0110(8) -0.0039(7) C34 0.0611(9) 0.0523(8) 0.0789(10) -0.0311(7) 0.0126(8) -0.0184(7) C35 0.0469(8) 0.0582(8) 0.0669(9) -0.0229(7) -0.0003(6) -0.0123(6) C36 0.0442(7) 0.0428(6) 0.0520(7) -0.0148(5) 0.0009(5) -0.0045(5) _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 C7 1.3521(16) . ? O1 C4 1.4077(15) . ? O2 C7 1.1921(17) . ? O3 C17 1.368(4) . ? O3 C14 1.386(2) . ? O4 C17 1.196(4) . ? O3A C17A 1.401(10) . ? O3A C14 1.486(9) . ? O4A C17A 1.142(11) . ? C1 C6 1.3974(17) . ? C1 C2 1.3976(17) . ? C1 C10 1.4924(16) . ? C2 C3 1.3870(18) . ? C3 C4 1.3836(19) . ? C4 C5 1.3787(18) . ? C5 C6 1.3880(17) . ? C7 C8 1.476(2) . ? C8 C9 1.301(2) . ? C10 C20 1.3557(17) . ? C10 C11 1.4956(15) . ? C11 C16 1.3924(17) . ? C11 C12 1.3927(16) . ? C12 C13 1.3861(17) . ? C13 C14 1.3787(18) . ? C14 C15 1.3800(18) . ? C15 C16 1.3819(17) . ? C17 C18 1.466(3) . ? C18 C19 1.306(3) . ? C17A C18A 1.502(10) . ? C18A C19A 1.280(9) . ? C20 C31 1.4938(16) . ? C20 C21 1.4961(16) . ? C21 C26 1.3934(17) . ? C21 C22 1.3943(17) . ? C22 C23 1.3847(18) . ? C23 C24 1.382(2) . ? C24 C25 1.383(2) . ? C25 C26 1.3813(19) . ? C31 C36 1.3862(18) . ? C31 C32 1.3914(18) . ? C32 C33 1.382(2) . ? C33 C34 1.377(2) . ? C34 C35 1.377(2) . ? C35 C36 1.3888(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 C7 O1 C4 120.16(10) . . ? C17 O3 C14 116.40(19) . . ? C17A O3A C14 118.2(6) . . ? C6 C1 C2 117.65(11) . . ? C6 C1 C10 120.15(10) . . ? C2 C1 C10 122.16(11) . . ? C3 C2 C1 121.46(12) . . ? C4 C3 C2 119.00(11) . . ? C5 C4 C3 121.35(11) . . ? C5 C4 O1 116.17(11) . . ? C3 C4 O1 122.28(11) . . ? C4 C5 C6 118.95(12) . . ? C5 C6 C1 121.58(11) . . ? O2 C7 O1 123.66(12) . . ? O2 C7 C8 125.09(14) . . ? O1 C7 C8 111.23(12) . . ? C9 C8 C7 120.84(16) . . ? C20 C10 C1 123.80(10) . . ? C20 C10 C11 121.11(10) . . ? C1 C10 C11 115.05(9) . . ? C16 C11 C12 118.32(11) . . ? C16 C11 C10 120.53(10) . . ? C12 C11 C10 121.14(10) . . ? C13 C12 C11 121.10(11) . . ? C14 C13 C12 118.89(11) . . ? C13 C14 C15 121.51(11) . . ? C13 C14 O3 117.11(13) . . ? C15 C14 O3 120.67(14) . . ? C13 C14 O3A 122.9(3) . . ? C15 C14 O3A 115.2(3) . . ? O3 C14 O3A 15.9(3) . . ? C14 C15 C16 118.95(11) . . ? C15 C16 C11 121.22(11) . . ? O4 C17 O3 122.2(2) . . ? O4 C17 C18 129.0(3) . . ? O3 C17 C18 108.8(2) . . ? C19 C18 C17 120.8(3) . . ? O4A C17A O3A 124.2(8) . . ? O4A C17A C18A 126.8(9) . . ? O3A C17A C18A 108.8(8) . . ? C19A C18A C17A 126.1(8) . . ? C10 C20 C31 123.20(11) . . ? C10 C20 C21 122.33(10) . . ? C31 C20 C21 114.20(9) . . ? C26 C21 C22 117.82(11) . . ? C26 C21 C20 122.68(10) . . ? C22 C21 C20 119.46(10) . . ? C23 C22 C21 121.38(11) . . ? C24 C23 C22 119.86(12) . . ? C23 C24 C25 119.46(12) . . ? C26 C25 C24 120.63(13) . . ? C25 C26 C21 120.75(12) . . ? C36 C31 C32 118.39(12) . . ? C36 C31 C20 120.34(11) . . ? C32 C31 C20 121.00(12) . . ? C33 C32 C31 120.59(14) . . ? C34 C33 C32 120.51(13) . . ? C35 C34 C33 119.56(13) . . ? C34 C35 C36 120.18(14) . . ? C31 C36 C35 120.75(12) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 66.50 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.185 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.030 # Attachment '- E2.cif' data_rong6cult _database_code_depnum_ccdc_archive 'CCDC 885936' #TrackingRef '- E2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 O4' _chemical_formula_weight 472.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 '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 9.5026(11) _cell_length_b 12.2523(14) _cell_length_c 12.4543(8) _cell_angle_alpha 98.109(7) _cell_angle_beta 110.976(8) _cell_angle_gamma 105.891(10) _cell_volume 1255.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3165 _cell_measurement_theta_min 3.88 _cell_measurement_theta_max 71.22 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.655 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6598 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.94 _diffrn_reflns_theta_max 67.48 _reflns_number_total 4371 _reflns_number_gt 3273 _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^)+(0.0980P)^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 4371 _refine_ls_number_parameters 324 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1498 _refine_ls_wR_factor_gt 0.1425 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.81851(16) 1.07452(12) 0.89316(13) 0.0555(4) Uani 1 1 d . . . O2 O 0.5650(4) 1.0175(3) 0.8777(3) 0.0598(8) Uiso 0.50 1 d P . . O2A O 0.5831(5) 0.9780(4) 0.8990(4) 0.0711(10) Uiso 0.50 1 d P . . O3 O 0.47946(16) 0.29119(12) 0.03801(13) 0.0543(4) Uani 1 1 d . . . O4 O 0.22994(17) 0.29951(14) -0.01956(14) 0.0642(4) Uani 1 1 d . . . C1 C 0.6949(2) 0.83012(15) 0.57505(16) 0.0396(4) Uani 1 1 d . . . C2 C 0.7800(2) 0.81454(15) 0.68604(16) 0.0411(4) Uani 1 1 d . . . H2A H 0.8116 0.7475 0.6893 0.049 Uiso 1 1 calc R . . C3 C 0.8187(2) 0.89517(16) 0.79120(17) 0.0453(4) Uani 1 1 d . . . H3A H 0.8764 0.8836 0.8660 0.054 Uiso 1 1 calc R . . C4 C 0.7730(2) 0.99211(16) 0.78637(17) 0.0450(4) Uani 1 1 d . . . C5 C 0.6922(2) 1.01216(17) 0.67824(18) 0.0509(5) Uani 1 1 d . . . H5A H 0.6642 1.0808 0.6759 0.061 Uiso 1 1 calc R . . C6 C 0.6533(2) 0.93074(17) 0.57411(18) 0.0478(5) Uani 1 1 d . . . H6A H 0.5965 0.9436 0.4998 0.057 Uiso 1 1 calc R . . C7 C 0.7063(3) 1.0692(2) 0.9373(2) 0.0636(6) Uani 1 1 d . . . C8 C 0.7665(3) 1.1612(2) 1.0494(2) 0.0698(7) Uani 1 1 d . . . H8A H 0.7015 1.1569 1.0926 0.084 Uiso 1 1 calc R . . C9 C 0.9047(3) 1.2485(2) 1.0929(2) 0.0694(7) Uani 1 1 d . . . H9A H 0.9724 1.2551 1.0516 0.083 Uiso 1 1 calc R . . H9B H 0.9372 1.3052 1.1655 0.083 Uiso 1 1 calc R . . C10 C 0.6411(2) 0.73875(15) 0.46178(15) 0.0378(4) Uani 1 1 d . . . C11 C 0.67113(19) 0.57952(14) 0.33338(15) 0.0364(4) Uani 1 1 d . . . C12 C 0.5485(2) 0.47894(16) 0.32184(17) 0.0425(4) Uani 1 1 d . . . H12A H 0.5087 0.4763 0.3818 0.051 Uiso 1 1 calc R . . C13 C 0.4843(2) 0.38314(16) 0.22425(18) 0.0461(4) Uani 1 1 d . . . H13A H 0.4023 0.3141 0.2176 0.055 Uiso 1 1 calc R . . C14 C 0.5402(2) 0.38835(15) 0.13626(17) 0.0438(4) Uani 1 1 d . . . C15 C 0.6642(2) 0.48582(16) 0.14592(17) 0.0435(4) Uani 1 1 d . . . H15A H 0.7028 0.4880 0.0854 0.052 Uiso 1 1 calc R . . C16 C 0.73068(19) 0.58036(15) 0.24640(16) 0.0400(4) Uani 1 1 d . . . H16A H 0.8184 0.6468 0.2558 0.048 Uiso 1 1 calc R . . C17 C 0.3193(2) 0.25146(17) -0.03308(19) 0.0504(5) Uani 1 1 d . . . C18 C 0.2737(3) 0.14490(19) -0.1276(2) 0.0627(6) Uani 1 1 d . . . H18A H 0.3484 0.1063 -0.1253 0.075 Uiso 1 1 calc R . . C19 C 0.1289(3) 0.1036(2) -0.2151(2) 0.0773(8) Uani 1 1 d . . . H19A H 0.0544 0.1424 -0.2171 0.093 Uiso 1 1 calc R . . H19B H 0.0987 0.0349 -0.2763 0.093 Uiso 1 1 calc R . . C20 C 0.73684(19) 0.68476(14) 0.43753(15) 0.0369(4) Uani 1 1 d . . . C21 C 0.91283(19) 0.72228(14) 0.51136(15) 0.0364(4) Uani 1 1 d . . . C22 C 0.9800(2) 0.64269(16) 0.55845(16) 0.0430(4) Uani 1 1 d . . . H22A H 0.9123 0.5637 0.5421 0.052 Uiso 1 1 calc R . . C23 C 1.1428(2) 0.67590(18) 0.62847(17) 0.0515(5) Uani 1 1 d . . . H23A H 1.1855 0.6206 0.6614 0.062 Uiso 1 1 calc R . . C24 C 1.2438(2) 0.7901(2) 0.65046(18) 0.0563(6) Uani 1 1 d . . . H24A H 1.3559 0.8136 0.6984 0.068 Uiso 1 1 calc R . . C25 C 1.1799(2) 0.86918(19) 0.6020(2) 0.0585(6) Uani 1 1 d . . . H25A H 1.2490 0.9472 0.6161 0.070 Uiso 1 1 calc R . . C26 C 1.0162(2) 0.83663(16) 0.53300(18) 0.0471(5) Uani 1 1 d . . . H26A H 0.9742 0.8924 0.5003 0.057 Uiso 1 1 calc R . . C31 C 0.4692(2) 0.70663(15) 0.37718(16) 0.0405(4) Uani 1 1 d . . . C32 C 0.3476(2) 0.68495(18) 0.41753(18) 0.0486(5) Uani 1 1 d . . . H32A H 0.3753 0.6927 0.5002 0.058 Uiso 1 1 calc R . . C33 C 0.1875(2) 0.6524(2) 0.3399(2) 0.0587(5) Uani 1 1 d . . . H33A H 0.1064 0.6373 0.3691 0.070 Uiso 1 1 calc R . . C34 C 0.1456(3) 0.6419(2) 0.2187(2) 0.0645(6) Uani 1 1 d . . . H34A H 0.0359 0.6187 0.1646 0.077 Uiso 1 1 calc R . . C35 C 0.2645(3) 0.6654(2) 0.17815(19) 0.0612(6) Uani 1 1 d . . . H35A H 0.2362 0.6592 0.0957 0.073 Uiso 1 1 calc R . . C36 C 0.4248(2) 0.69791(18) 0.25526(17) 0.0481(5) Uani 1 1 d . . . H36A H 0.5052 0.7144 0.2255 0.058 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0506(7) 0.0574(8) 0.0497(8) -0.0045(6) 0.0181(6) 0.0191(6) O3 0.0475(7) 0.0467(7) 0.0538(8) -0.0076(6) 0.0155(6) 0.0127(6) O4 0.0470(7) 0.0659(9) 0.0597(9) -0.0043(7) 0.0123(7) 0.0141(7) C1 0.0371(8) 0.0430(9) 0.0410(9) 0.0090(7) 0.0164(7) 0.0184(7) C2 0.0439(9) 0.0413(9) 0.0432(10) 0.0120(7) 0.0185(8) 0.0215(7) C3 0.0450(9) 0.0503(10) 0.0400(10) 0.0094(8) 0.0161(8) 0.0193(8) C4 0.0401(9) 0.0456(10) 0.0432(10) 0.0012(8) 0.0149(8) 0.0145(7) C5 0.0526(10) 0.0458(10) 0.0521(11) 0.0047(8) 0.0142(9) 0.0284(8) C6 0.0499(10) 0.0493(10) 0.0430(10) 0.0085(8) 0.0123(8) 0.0271(8) C7 0.0562(12) 0.0778(15) 0.0499(12) 0.0032(11) 0.0214(10) 0.0207(11) C8 0.0710(15) 0.0926(17) 0.0459(12) 0.0038(12) 0.0205(11) 0.0412(14) C9 0.0790(16) 0.0778(15) 0.0423(11) 0.0006(11) 0.0090(11) 0.0436(13) C10 0.0383(8) 0.0392(9) 0.0393(9) 0.0104(7) 0.0160(7) 0.0187(7) C11 0.0309(7) 0.0369(8) 0.0380(9) 0.0054(7) 0.0104(7) 0.0146(6) C12 0.0395(8) 0.0439(9) 0.0441(10) 0.0105(8) 0.0179(8) 0.0147(7) C13 0.0384(9) 0.0392(9) 0.0497(11) 0.0047(8) 0.0135(8) 0.0075(7) C14 0.0391(9) 0.0367(9) 0.0435(10) -0.0011(7) 0.0089(7) 0.0124(7) C15 0.0403(9) 0.0467(10) 0.0403(9) 0.0040(7) 0.0162(8) 0.0151(7) C16 0.0325(8) 0.0389(8) 0.0436(10) 0.0041(7) 0.0140(7) 0.0111(7) C17 0.0454(10) 0.0444(10) 0.0502(11) 0.0027(8) 0.0184(9) 0.0064(8) C18 0.0616(13) 0.0475(11) 0.0603(14) -0.0037(10) 0.0242(11) 0.0020(9) C19 0.0662(14) 0.0614(14) 0.0703(16) -0.0137(12) 0.0239(13) -0.0061(11) C20 0.0368(8) 0.0363(8) 0.0376(9) 0.0077(7) 0.0144(7) 0.0151(7) C21 0.0363(8) 0.0372(8) 0.0342(8) 0.0012(6) 0.0147(7) 0.0146(7) C22 0.0398(9) 0.0416(9) 0.0420(10) 0.0028(7) 0.0123(7) 0.0166(7) C23 0.0444(10) 0.0614(12) 0.0430(10) 0.0022(9) 0.0098(8) 0.0270(9) C24 0.0351(9) 0.0711(13) 0.0454(11) -0.0088(10) 0.0091(8) 0.0155(9) C25 0.0451(10) 0.0493(11) 0.0617(13) -0.0077(10) 0.0215(9) 0.0000(9) C26 0.0477(10) 0.0379(9) 0.0505(11) 0.0041(8) 0.0199(9) 0.0117(8) C31 0.0415(9) 0.0436(9) 0.0391(9) 0.0086(7) 0.0146(7) 0.0227(7) C32 0.0440(9) 0.0626(11) 0.0420(10) 0.0112(9) 0.0170(8) 0.0255(9) C33 0.0419(10) 0.0739(14) 0.0626(13) 0.0164(11) 0.0212(9) 0.0253(9) C34 0.0439(10) 0.0798(15) 0.0549(13) 0.0055(11) 0.0046(9) 0.0275(10) C35 0.0640(12) 0.0792(14) 0.0400(11) 0.0116(10) 0.0115(10) 0.0401(11) C36 0.0512(10) 0.0590(11) 0.0426(10) 0.0152(8) 0.0191(8) 0.0316(9) _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 C7 1.354(3) . ? O1 C4 1.395(2) . ? O2 O2A 0.619(5) . ? O2 C7 1.201(4) . ? O2A C7 1.257(4) . ? O3 C17 1.358(2) . ? O3 C14 1.398(2) . ? O4 C17 1.202(3) . ? C1 C6 1.395(3) . ? C1 C2 1.400(3) . ? C1 C10 1.493(2) . ? C2 C3 1.385(3) . ? C3 C4 1.374(3) . ? C4 C5 1.386(3) . ? C5 C6 1.380(3) . ? C7 C8 1.476(3) . ? C8 C9 1.312(4) . ? C10 C20 1.352(2) . ? C10 C31 1.494(2) . ? C11 C16 1.390(3) . ? C11 C12 1.393(3) . ? C11 C20 1.497(2) . ? C12 C13 1.379(3) . ? C13 C14 1.380(3) . ? C14 C15 1.384(3) . ? C15 C16 1.390(2) . ? C17 C18 1.473(3) . ? C18 C19 1.314(3) . ? C20 C21 1.487(2) . ? C21 C22 1.391(3) . ? C21 C26 1.397(2) . ? C22 C23 1.382(3) . ? C23 C24 1.386(3) . ? C24 C25 1.377(3) . ? C25 C26 1.387(3) . ? C31 C32 1.394(3) . ? C31 C36 1.402(3) . ? C32 C33 1.384(3) . ? C33 C34 1.393(3) . ? C34 C35 1.373(3) . ? C35 C36 1.383(3) . ? 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 C7 O1 C4 117.17(15) . . ? O2A O2 C7 80.5(6) . . ? O2 O2A C7 70.5(5) . . ? C17 O3 C14 117.82(15) . . ? C6 C1 C2 117.66(16) . . ? C6 C1 C10 120.87(16) . . ? C2 C1 C10 121.35(15) . . ? C3 C2 C1 121.12(16) . . ? C4 C3 C2 119.37(17) . . ? C3 C4 C5 121.23(17) . . ? C3 C4 O1 118.45(17) . . ? C5 C4 O1 120.20(17) . . ? C6 C5 C4 118.82(17) . . ? C5 C6 C1 121.76(18) . . ? O2 C7 O2A 29.0(2) . . ? O2 C7 O1 122.7(2) . . ? O2A C7 O1 119.7(3) . . ? O2 C7 C8 122.0(3) . . ? O2A C7 C8 125.6(3) . . ? O1 C7 C8 112.61(19) . . ? C9 C8 C7 123.8(2) . . ? C20 C10 C1 123.44(15) . . ? C20 C10 C31 121.47(15) . . ? C1 C10 C31 115.05(14) . . ? C16 C11 C12 118.80(15) . . ? C16 C11 C20 120.79(15) . . ? C12 C11 C20 120.41(16) . . ? C13 C12 C11 120.60(18) . . ? C12 C13 C14 119.45(17) . . ? C13 C14 C15 121.52(16) . . ? C13 C14 O3 120.34(16) . . ? C15 C14 O3 118.02(17) . . ? C14 C15 C16 118.33(18) . . ? C15 C16 C11 121.19(16) . . ? O4 C17 O3 123.31(17) . . ? O4 C17 C18 125.78(18) . . ? O3 C17 C18 110.90(18) . . ? C19 C18 C17 119.6(2) . . ? C10 C20 C21 123.69(15) . . ? C10 C20 C11 121.71(15) . . ? C21 C20 C11 114.60(14) . . ? C22 C21 C26 117.95(16) . . ? C22 C21 C20 120.54(15) . . ? C26 C21 C20 121.49(16) . . ? C23 C22 C21 121.56(17) . . ? C22 C23 C24 119.85(19) . . ? C25 C24 C23 119.33(18) . . ? C24 C25 C26 121.00(19) . . ? C25 C26 C21 120.27(19) . . ? C32 C31 C36 117.85(17) . . ? C32 C31 C10 120.78(16) . . ? C36 C31 C10 121.37(16) . . ? C33 C32 C31 121.47(19) . . ? C32 C33 C34 119.8(2) . . ? C35 C34 C33 119.36(19) . . ? C34 C35 C36 121.2(2) . . ? C35 C36 C31 120.36(19) . . ? 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 C6 C1 C2 C3 1.1(3) . . . . ? C10 C1 C2 C3 -174.93(16) . . . . ? C1 C2 C3 C4 -0.1(3) . . . . ? C2 C3 C4 C5 -1.6(3) . . . . ? C2 C3 C4 O1 -177.62(16) . . . . ? C7 O1 C4 C3 -100.2(2) . . . . ? C7 O1 C4 C5 83.8(3) . . . . ? C3 C4 C5 C6 2.0(3) . . . . ? O1 C4 C5 C6 178.01(17) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? C10 C1 C6 C5 175.43(18) . . . . ? O2A O2 C7 O1 93.2(6) . . . . ? O2A O2 C7 C8 -106.7(6) . . . . ? O2 O2A C7 O1 -104.7(6) . . . . ? O2 O2A C7 C8 93.1(6) . . . . ? C4 O1 C7 O2 -17.5(4) . . . . ? C4 O1 C7 O2A 16.4(4) . . . . ? C4 O1 C7 C8 -179.24(19) . . . . ? O2 C7 C8 C9 -152.8(3) . . . . ? O2A C7 C8 C9 172.3(4) . . . . ? O1 C7 C8 C9 9.1(4) . . . . ? C6 C1 C10 C20 138.2(2) . . . . ? C2 C1 C10 C20 -45.9(3) . . . . ? C6 C1 C10 C31 -44.2(2) . . . . ? C2 C1 C10 C31 131.75(18) . . . . ? C16 C11 C12 C13 -1.8(3) . . . . ? C20 C11 C12 C13 178.04(16) . . . . ? C11 C12 C13 C14 -1.3(3) . . . . ? C12 C13 C14 C15 2.7(3) . . . . ? C12 C13 C14 O3 178.47(16) . . . . ? C17 O3 C14 C13 60.3(3) . . . . ? C17 O3 C14 C15 -123.8(2) . . . . ? C13 C14 C15 C16 -0.9(3) . . . . ? O3 C14 C15 C16 -176.77(16) . . . . ? C14 C15 C16 C11 -2.3(3) . . . . ? C12 C11 C16 C15 3.6(3) . . . . ? C20 C11 C16 C15 -176.20(16) . . . . ? C14 O3 C17 O4 4.4(3) . . . . ? C14 O3 C17 C18 -176.53(18) . . . . ? O4 C17 C18 C19 8.9(4) . . . . ? O3 C17 C18 C19 -170.2(2) . . . . ? C1 C10 C20 C21 -9.8(3) . . . . ? C31 C10 C20 C21 172.74(16) . . . . ? C1 C10 C20 C11 169.17(16) . . . . ? C31 C10 C20 C11 -8.3(3) . . . . ? C16 C11 C20 C10 122.8(2) . . . . ? C12 C11 C20 C10 -57.0(2) . . . . ? C16 C11 C20 C21 -58.2(2) . . . . ? C12 C11 C20 C21 122.00(18) . . . . ? C10 C20 C21 C22 124.7(2) . . . . ? C11 C20 C21 C22 -54.3(2) . . . . ? C10 C20 C21 C26 -57.0(3) . . . . ? C11 C20 C21 C26 124.00(18) . . . . ? C26 C21 C22 C23 2.5(3) . . . . ? C20 C21 C22 C23 -179.22(17) . . . . ? C21 C22 C23 C24 -1.7(3) . . . . ? C22 C23 C24 C25 0.0(3) . . . . ? C23 C24 C25 C26 0.8(3) . . . . ? C24 C25 C26 C21 0.0(3) . . . . ? C22 C21 C26 C25 -1.6(3) . . . . ? C20 C21 C26 C25 -179.90(18) . . . . ? C20 C10 C31 C32 131.8(2) . . . . ? C1 C10 C31 C32 -45.9(2) . . . . ? C20 C10 C31 C36 -48.6(3) . . . . ? C1 C10 C31 C36 133.74(18) . . . . ? C36 C31 C32 C33 1.9(3) . . . . ? C10 C31 C32 C33 -178.47(19) . . . . ? C31 C32 C33 C34 -0.6(3) . . . . ? C32 C33 C34 C35 -0.7(4) . . . . ? C33 C34 C35 C36 0.8(4) . . . . ? C34 C35 C36 C31 0.6(3) . . . . ? C32 C31 C36 C35 -1.8(3) . . . . ? C10 C31 C36 C35 178.50(18) . . . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 66.50 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.306 _refine_diff_density_min -0.330 _refine_diff_density_rms 0.043 # Attachment '- 16.cif' data_rong5 _database_code_depnum_ccdc_archive 'CCDC 885937' #TrackingRef '- 16.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H22 O4' _chemical_formula_weight 458.49 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 17.330(8) _cell_length_b 9.333(4) _cell_length_c 13.964(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.064(6) _cell_angle_gamma 90.00 _cell_volume 2230.2(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1980 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 28.28 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6479 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0588 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2159 _reflns_number_gt 1832 _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^)+(0.0325P)^2^+2.9993P] 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 2159 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1109 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.29015(8) 0.54232(14) 0.47835(9) 0.0230(3) Uani 1 1 d . . . O2 O 0.33075(10) 0.42103(17) 0.35702(10) 0.0381(4) Uani 1 1 d . . . C1 C 0.53759(10) 0.10933(18) 0.68621(12) 0.0156(4) Uani 1 1 d . . . C2 C 0.52189(10) -0.03242(18) 0.70888(13) 0.0173(4) Uani 1 1 d . . . C3 C 0.54594(11) -0.1452(2) 0.65595(13) 0.0205(4) Uani 1 1 d . . . H3A H 0.5349 -0.2414 0.6712 0.025 Uiso 1 1 calc R . . C4 C 0.58641(11) -0.1146(2) 0.58026(13) 0.0231(4) Uani 1 1 d . . . H4A H 0.6025 -0.1905 0.5427 0.028 Uiso 1 1 calc R . . C5 C 0.60355(11) 0.0260(2) 0.55896(13) 0.0230(4) Uani 1 1 d . . . H5A H 0.6322 0.0450 0.5077 0.028 Uiso 1 1 calc R . . C6 C 0.57937(11) 0.1392(2) 0.61150(13) 0.0188(4) Uani 1 1 d . . . H6A H 0.5912 0.2352 0.5966 0.023 Uiso 1 1 calc R . . C10 C 0.5000 0.2146(3) 0.7500 0.0146(5) Uani 1 2 d S . . C11 C 0.44173(10) 0.30751(18) 0.68306(12) 0.0149(4) Uani 1 1 d . . . C12 C 0.36292(10) 0.27162(19) 0.66080(12) 0.0171(4) Uani 1 1 d . . . H12A H 0.3432 0.1929 0.6927 0.021 Uiso 1 1 calc R . . C13 C 0.31274(11) 0.34957(19) 0.59256(13) 0.0190(4) Uani 1 1 d . . . H13A H 0.2589 0.3252 0.5783 0.023 Uiso 1 1 calc R . . C14 C 0.34175(11) 0.46197(19) 0.54609(13) 0.0190(4) Uani 1 1 d . . . C15 C 0.41899(11) 0.50283(19) 0.56809(13) 0.0196(4) Uani 1 1 d . . . H15A H 0.4379 0.5828 0.5366 0.023 Uiso 1 1 calc R . . C16 C 0.46861(11) 0.42569(18) 0.63678(13) 0.0177(4) Uani 1 1 d . . . H16A H 0.5218 0.4537 0.6526 0.021 Uiso 1 1 calc R . . C17 C 0.28971(11) 0.51083(19) 0.38303(13) 0.0192(4) Uani 1 1 d . . . C18 C 0.23334(11) 0.5996(2) 0.31835(13) 0.0215(4) Uani 1 1 d . . . H18A H 0.2199 0.5707 0.2526 0.026 Uiso 1 1 calc R . . C19 C 0.20073(13) 0.7155(2) 0.34603(15) 0.0302(5) Uani 1 1 d . . . H19A H 0.2129 0.7471 0.4113 0.036 Uiso 1 1 calc R . . H19B H 0.1648 0.7681 0.3009 0.036 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0248(8) 0.0288(7) 0.0133(6) 0.0012(5) -0.0041(6) 0.0113(6) O2 0.0473(10) 0.0446(9) 0.0199(7) -0.0054(7) -0.0025(7) 0.0237(8) C1 0.0111(8) 0.0197(9) 0.0133(8) -0.0004(7) -0.0065(7) 0.0018(7) C2 0.0129(9) 0.0216(9) 0.0147(9) -0.0003(7) -0.0066(7) 0.0005(7) C3 0.0180(10) 0.0196(9) 0.0203(9) -0.0021(7) -0.0078(8) 0.0019(7) C4 0.0188(10) 0.0277(10) 0.0203(10) -0.0085(8) -0.0042(8) 0.0072(8) C5 0.0171(10) 0.0370(11) 0.0139(9) -0.0003(8) -0.0007(8) 0.0052(8) C6 0.0170(9) 0.0227(9) 0.0148(9) 0.0030(7) -0.0036(7) 0.0015(7) C10 0.0140(12) 0.0170(12) 0.0116(11) 0.000 -0.0021(10) 0.000 C11 0.0162(9) 0.0175(8) 0.0101(8) -0.0039(6) -0.0008(7) 0.0033(7) C12 0.0162(9) 0.0201(9) 0.0140(8) -0.0019(7) -0.0008(7) -0.0006(7) C13 0.0157(9) 0.0239(9) 0.0158(9) -0.0060(7) -0.0027(7) 0.0011(7) C14 0.0224(10) 0.0217(9) 0.0107(8) -0.0021(7) -0.0041(7) 0.0094(8) C15 0.0241(10) 0.0187(9) 0.0156(9) 0.0032(7) 0.0020(8) 0.0032(8) C16 0.0141(9) 0.0208(9) 0.0168(9) -0.0006(7) -0.0014(7) 0.0010(7) C17 0.0211(10) 0.0204(9) 0.0147(9) -0.0016(7) -0.0018(8) -0.0011(8) C18 0.0209(10) 0.0274(10) 0.0141(9) 0.0024(7) -0.0034(7) -0.0023(8) C19 0.0351(12) 0.0300(11) 0.0207(10) 0.0004(8) -0.0102(9) 0.0093(9) _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 C17 1.362(2) . ? O1 C14 1.411(2) . ? O2 C17 1.192(2) . ? C1 C6 1.389(2) . ? C1 C2 1.397(2) . ? C1 C10 1.538(2) . ? C2 C3 1.387(2) . ? C2 C2 1.473(4) 2_656 ? C3 C4 1.387(3) . ? C4 C5 1.388(3) . ? C5 C6 1.388(3) . ? C10 C11 1.532(2) 2_656 ? C10 C11 1.532(2) . ? C10 C1 1.538(2) 2_656 ? C11 C12 1.393(3) . ? C11 C16 1.395(2) . ? C12 C13 1.390(3) . ? C13 C14 1.370(3) . ? C14 C15 1.379(3) . ? C15 C16 1.385(3) . ? C17 C18 1.476(3) . ? C18 C19 1.307(3) . ? 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 C17 O1 C14 116.48(14) . . ? C6 C1 C2 120.22(16) . . ? C6 C1 C10 128.71(16) . . ? C2 C1 C10 111.01(15) . . ? C3 C2 C1 120.80(17) . . ? C3 C2 C2 130.57(11) . 2_656 ? C1 C2 C2 108.62(10) . 2_656 ? C2 C3 C4 118.71(17) . . ? C3 C4 C5 120.58(17) . . ? C6 C5 C4 120.89(17) . . ? C5 C6 C1 118.77(17) . . ? C11 C10 C11 111.1(2) 2_656 . ? C11 C10 C1 114.59(9) 2_656 . ? C11 C10 C1 107.86(9) . . ? C11 C10 C1 107.86(9) 2_656 2_656 ? C11 C10 C1 114.59(10) . 2_656 ? C1 C10 C1 100.58(19) . 2_656 ? C12 C11 C16 118.29(16) . . ? C12 C11 C10 121.94(15) . . ? C16 C11 C10 119.59(15) . . ? C13 C12 C11 120.84(17) . . ? C14 C13 C12 119.26(17) . . ? C13 C14 C15 121.46(17) . . ? C13 C14 O1 118.91(17) . . ? C15 C14 O1 119.53(16) . . ? C14 C15 C16 119.05(17) . . ? C15 C16 C11 121.04(17) . . ? O2 C17 O1 122.52(17) . . ? O2 C17 C18 125.25(17) . . ? O1 C17 C18 112.22(15) . . ? C19 C18 C17 123.98(18) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.266 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.051