# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ruqiang Zou' _publ_contact_author_email rzou@pku.edu.cn _publ_author_name 'Ruqiang Zou' data_Pr-LOF-Platon _database_code_depnum_ccdc_archive 'CCDC 881994' #TrackingRef 'Pr-LOF-Platon.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H17 O7 Pr' _chemical_formula_weight 594.32 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' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6122 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' 'y, x, -z+1/3' 'x-y, -y, -z' '-x, -x+y, -z+2/3' '-y, -x, -z+5/6' '-x+y, y, -z+1/2' 'x, x-y, -z+1/6' _cell_length_a 16.4393(3) _cell_length_b 16.4393(3) _cell_length_c 23.7770(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5564.9(3) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Green _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.064 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1764 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6854 _exptl_absorpt_correction_T_max 0.8758 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 73752 _diffrn_reflns_av_R_equivalents 0.1063 _diffrn_reflns_av_sigmaI/netI 0.0606 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 27.60 _reflns_number_total 4317 _reflns_number_gt 3617 _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^)+(0.0508P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_number_reflns 4317 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0899 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _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 Pr1 Pr 0.91567(2) 1.0000 0.0000 0.02112(10) Uani 1 2 d S . . C1 C 0.8243(3) 0.8004(3) 0.0363(2) 0.0311(12) Uani 1 1 d . . . C2 C 0.7863(3) 0.6970(3) 0.0415(2) 0.0294(11) Uani 1 1 d . . . C3 C 0.8315(4) 0.6604(3) 0.0746(2) 0.0276(11) Uani 1 1 d . . . H3 H 0.8891 0.7012 0.0910 0.033 Uiso 1 1 calc R . . C4 C 0.7928(3) 0.5669(3) 0.0829(2) 0.0295(11) Uani 1 1 d . . . H4 H 0.8223 0.5445 0.1065 0.035 Uiso 1 1 calc R . . C5 C 0.7069(4) 0.5024(3) 0.0559(2) 0.0322(12) Uani 1 1 d . . . C6 C 0.6669(4) 0.5386(4) 0.0207(2) 0.0403(14) Uani 1 1 d . . . H6 H 0.6131 0.4977 0.0008 0.048 Uiso 1 1 calc R . . C7 C 0.7048(3) 0.6350(3) 0.0141(2) 0.0393(14) Uani 1 1 d . . . H7 H 0.6749 0.6576 -0.0090 0.047 Uiso 1 1 calc R . . C8 C 0.6579(4) 0.4014(3) 0.0697(2) 0.0322(11) Uani 1 1 d . . . C9 C 0.7069(5) 0.3535(2) 0.0833 0.0330(17) Uani 1 2 d S . . H9 H 0.7723 0.3861 0.0833 0.040 Uiso 1 2 calc SR . . C10 C 0.5615(4) 0.3498(4) 0.0687(3) 0.0425(14) Uani 1 1 d . . . H10 H 0.5284 0.3794 0.0577 0.051 Uiso 1 1 calc R . . C11 C 0.5115(5) 0.2557(3) 0.0833 0.046(2) Uani 1 2 d S . . C12 C 0.4053(5) 0.2027(3) 0.0833 0.041(2) Uani 1 2 d S . . C13 C 0.3567(4) 0.2233(5) 0.0424(3) 0.063(2) Uani 1 1 d . . . H13 H 0.3891 0.2690 0.0153 0.076 Uiso 1 1 calc R . . C14 C 0.2597(4) 0.1741(5) 0.0434(3) 0.0571(17) Uani 1 1 d . . . H14 H 0.2267 0.1875 0.0167 0.069 Uiso 1 1 calc R . . C15 C 0.2103(5) 0.1052(2) 0.0833 0.0373(19) Uani 1 2 d S . . C16 C 0.1053(5) 0.0527(2) 0.0833 0.0338(17) Uani 1 2 d S . . O1 O 0.8911(2) 0.8580(2) 0.06836(14) 0.0299(7) Uani 1 1 d . . . O2 O 0.7898(3) 0.8308(2) 0.0021(2) 0.0674(14) Uani 1 1 d . . . O3 O 0.0652(2) 0.0709(2) 0.04446(14) 0.0411(8) Uani 1 1 d . . . O1W O 0.7642(3) 1.0000 0.0000 0.0639(18) Uani 1 2 d S . . 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 Pr1 0.01506(13) 0.01563(18) 0.03285(17) 0.00561(17) 0.00281(8) 0.00781(9) C1 0.023(2) 0.022(2) 0.047(3) 0.010(2) 0.000(2) 0.010(2) C2 0.027(3) 0.023(2) 0.036(3) 0.004(2) 0.003(2) 0.011(2) C3 0.021(2) 0.020(2) 0.041(3) -0.006(2) -0.009(2) 0.010(2) C4 0.022(2) 0.024(3) 0.048(3) 0.003(2) -0.001(2) 0.016(2) C5 0.018(3) 0.018(2) 0.057(3) 0.000(2) 0.000(2) 0.007(2) C6 0.032(3) 0.026(3) 0.052(3) 0.003(2) -0.016(2) 0.006(2) C7 0.025(3) 0.024(3) 0.060(4) 0.015(2) -0.007(2) 0.005(2) C8 0.021(3) 0.020(2) 0.055(3) 0.003(2) -0.002(2) 0.009(2) C9 0.022(4) 0.016(2) 0.062(5) -0.001(3) 0.000 0.0112(19) C10 0.023(3) 0.027(3) 0.086(4) 0.007(3) -0.002(3) 0.018(2) C11 0.016(4) 0.023(3) 0.097(7) 0.009(4) 0.000 0.0079(19) C12 0.024(4) 0.021(3) 0.078(6) 0.002(3) 0.000 0.012(2) C13 0.019(3) 0.060(4) 0.098(5) 0.038(4) 0.007(3) 0.010(3) C14 0.027(3) 0.055(4) 0.070(4) 0.023(4) -0.006(3) 0.005(3) C15 0.021(4) 0.036(3) 0.051(5) 0.004(3) 0.000 0.0104(18) C16 0.018(4) 0.030(3) 0.050(4) -0.001(3) 0.000 0.0089(18) O1 0.037(2) 0.0188(16) 0.0370(17) 0.0012(14) 0.0034(16) 0.0160(16) O2 0.047(2) 0.024(2) 0.107(4) 0.023(3) -0.039(3) -0.0009(17) O3 0.0241(19) 0.040(2) 0.054(2) 0.0080(18) -0.0041(15) 0.0121(17) O1W 0.056(3) 0.090(5) 0.057(4) -0.039(4) -0.020(2) 0.045(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 Pr1 O3 2.378(3) 1_665 ? Pr1 O3 2.378(3) 8_665 ? Pr1 O1 2.478(3) 5_564 ? Pr1 O1 2.478(3) 12_565 ? Pr1 O1W 2.491(6) . ? Pr1 O2 2.504(3) . ? Pr1 O2 2.504(3) 8_675 ? Pr1 O1 2.704(3) 8_675 ? Pr1 O1 2.704(3) . ? Pr1 C1 2.974(4) . ? Pr1 C1 2.974(4) 8_675 ? C1 O2 1.231(6) . ? C1 O1 1.282(6) . ? C1 C2 1.494(6) . ? C2 C7 1.376(7) . ? C2 C3 1.407(7) . ? C3 C4 1.351(7) . ? C4 C5 1.426(7) . ? C5 C6 1.371(7) . ? C5 C8 1.475(6) . ? C6 C7 1.391(7) . ? C8 C10 1.374(7) . ? C8 C9 1.418(6) . ? C9 C8 1.418(6) 12 ? C10 C11 1.384(6) . ? C11 C10 1.384(6) 12 ? C11 C12 1.511(10) . ? C12 C13 1.404(7) . ? C12 C13 1.404(7) 12 ? C13 C14 1.381(7) . ? C14 C15 1.387(7) . ? C15 C14 1.387(7) 12 ? C15 C16 1.494(9) . ? C16 O3 1.256(4) . ? C16 O3 1.256(4) 12 ? O1 Pr1 2.478(3) 6_655 ? O3 Pr1 2.378(3) 1_445 ? 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 O3 Pr1 O3 75.9(2) 1_665 8_665 ? O3 Pr1 O1 135.65(11) 1_665 5_564 ? O3 Pr1 O1 73.43(11) 8_665 5_564 ? O3 Pr1 O1 73.43(12) 1_665 12_565 ? O3 Pr1 O1 135.65(11) 8_665 12_565 ? O1 Pr1 O1 148.36(15) 5_564 12_565 ? O3 Pr1 O1W 142.06(10) 1_665 . ? O3 Pr1 O1W 142.06(10) 8_665 . ? O1 Pr1 O1W 74.18(8) 5_564 . ? O1 Pr1 O1W 74.18(8) 12_565 . ? O3 Pr1 O2 127.82(12) 1_665 . ? O3 Pr1 O2 79.27(15) 8_665 . ? O1 Pr1 O2 76.26(13) 5_564 . ? O1 Pr1 O2 95.16(15) 12_565 . ? O1W Pr1 O2 74.29(10) . . ? O3 Pr1 O2 79.27(15) 1_665 8_675 ? O3 Pr1 O2 127.82(12) 8_665 8_675 ? O1 Pr1 O2 95.16(15) 5_564 8_675 ? O1 Pr1 O2 76.26(13) 12_565 8_675 ? O1W Pr1 O2 74.29(10) . 8_675 ? O2 Pr1 O2 148.59(19) . 8_675 ? O3 Pr1 O1 74.16(11) 1_665 8_675 ? O3 Pr1 O1 80.07(11) 8_665 8_675 ? O1 Pr1 O1 69.64(11) 5_564 8_675 ? O1 Pr1 O1 120.12(10) 12_565 8_675 ? O1W Pr1 O1 106.40(7) . 8_675 ? O2 Pr1 O1 143.92(15) . 8_675 ? O2 Pr1 O1 49.06(12) 8_675 8_675 ? O3 Pr1 O1 80.07(11) 1_665 . ? O3 Pr1 O1 74.16(11) 8_665 . ? O1 Pr1 O1 120.12(10) 5_564 . ? O1 Pr1 O1 69.64(11) 12_565 . ? O1W Pr1 O1 106.40(7) . . ? O2 Pr1 O1 49.06(12) . . ? O2 Pr1 O1 143.92(15) 8_675 . ? O1 Pr1 O1 147.20(15) 8_675 . ? O3 Pr1 C1 103.87(13) 1_665 . ? O3 Pr1 C1 71.72(13) 8_665 . ? O1 Pr1 C1 96.03(12) 5_564 . ? O1 Pr1 C1 85.43(12) 12_565 . ? O1W Pr1 C1 92.68(9) . . ? O2 Pr1 C1 24.07(12) . . ? O2 Pr1 C1 159.79(13) 8_675 . ? O1 Pr1 C1 151.16(12) 8_675 . ? O1 Pr1 C1 25.53(11) . . ? O3 Pr1 C1 71.72(13) 1_665 8_675 ? O3 Pr1 C1 103.87(13) 8_665 8_675 ? O1 Pr1 C1 85.43(12) 5_564 8_675 ? O1 Pr1 C1 96.03(12) 12_565 8_675 ? O1W Pr1 C1 92.68(9) . 8_675 ? O2 Pr1 C1 159.79(13) . 8_675 ? O2 Pr1 C1 24.07(12) 8_675 8_675 ? O1 Pr1 C1 25.53(11) 8_675 8_675 ? O1 Pr1 C1 151.16(12) . 8_675 ? C1 Pr1 C1 174.64(19) . 8_675 ? O2 C1 O1 119.4(4) . . ? O2 C1 C2 120.0(5) . . ? O1 C1 C2 120.6(4) . . ? O2 C1 Pr1 56.0(3) . . ? O1 C1 Pr1 65.4(2) . . ? C2 C1 Pr1 166.6(4) . . ? C7 C2 C3 118.3(4) . . ? C7 C2 C1 120.2(5) . . ? C3 C2 C1 121.5(4) . . ? C4 C3 C2 121.3(5) . . ? C3 C4 C5 120.5(5) . . ? C6 C5 C4 117.6(4) . . ? C6 C5 C8 120.9(5) . . ? C4 C5 C8 121.2(5) . . ? C5 C6 C7 121.6(5) . . ? C2 C7 C6 120.4(5) . . ? C10 C8 C9 117.5(4) . . ? C10 C8 C5 120.2(5) . . ? C9 C8 C5 122.3(5) . . ? C8 C9 C8 121.0(6) . 12 ? C8 C10 C11 122.9(5) . . ? C10 C11 C10 118.1(7) 12 . ? C10 C11 C12 121.0(3) 12 . ? C10 C11 C12 121.0(3) . . ? C13 C12 C13 120.9(7) . 12 ? C13 C12 C11 119.5(4) . . ? C13 C12 C11 119.5(4) 12 . ? C14 C13 C12 118.5(6) . . ? C13 C14 C15 121.5(6) . . ? C14 C15 C14 119.1(7) 12 . ? C14 C15 C16 120.5(4) 12 . ? C14 C15 C16 120.5(4) . . ? O3 C16 O3 125.9(6) . 12 ? O3 C16 C15 117.1(3) . . ? O3 C16 C15 117.1(3) 12 . ? C1 O1 Pr1 139.3(3) . 6_655 ? C1 O1 Pr1 89.1(3) . . ? Pr1 O1 Pr1 108.15(11) 6_655 . ? C1 O2 Pr1 99.9(3) . . ? C16 O3 Pr1 138.4(4) . 1_445 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.238 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.107 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.027 0.447 0.328 2777 1713 ' ' _platon_squeeze_details ; ; # Attachment 'Pr-LOF.cif' data_Pr-LOF _database_code_depnum_ccdc_archive 'CCDC 896622' #TrackingRef 'Pr-LOF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H31 N2 O9 Pr' _chemical_formula_weight 740.51 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6122 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' '-x, -y, z+1/2' 'y, -x+y, z+5/6' 'x-y, x, z+1/6' 'y, x, -z+1/3' 'x-y, -y, -z' '-x, -x+y, -z+2/3' '-y, -x, -z+5/6' '-x+y, y, -z+1/2' 'x, x-y, -z+1/6' _cell_length_a 16.4393(3) _cell_length_b 16.4393(3) _cell_length_c 23.7770(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5564.9(3) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour Green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2244 _exptl_absorpt_coefficient_mu 1.362 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6854 _exptl_absorpt_correction_T_max 0.8758 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 73752 _diffrn_reflns_av_R_equivalents 0.1106 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 27.60 _reflns_number_total 4317 _reflns_number_gt 3521 _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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(5) _refine_ls_number_reflns 4317 _refine_ls_number_parameters 186 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0897 _refine_ls_R_factor_gt 0.0707 _refine_ls_wR_factor_ref 0.2072 _refine_ls_wR_factor_gt 0.1949 _refine_ls_goodness_of_fit_ref 1.443 _refine_ls_restrained_S_all 1.517 _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 Pr1 Pr 0.91567(4) 1.0000 0.0000 0.0212(2) Uani 1 2 d S . . C1 C 0.8258(7) 0.8013(7) 0.0374(5) 0.031(2) Uani 1 1 d . . . C2 C 0.7883(7) 0.6967(7) 0.0420(4) 0.028(2) Uani 1 1 d . . . C3 C 0.8324(8) 0.6614(7) 0.0748(5) 0.029(2) Uani 1 1 d . . . H3 H 0.8896 0.7023 0.0916 0.034 Uiso 1 1 calc R . . C4 C 0.7928(7) 0.5663(7) 0.0828(5) 0.029(2) Uani 1 1 d . . . H4 H 0.8229 0.5439 0.1059 0.035 Uiso 1 1 calc R . . C5 C 0.7066(7) 0.5015(6) 0.0566(5) 0.031(2) Uani 1 1 d . . . C6 C 0.6662(9) 0.5380(8) 0.0213(5) 0.042(3) Uani 1 1 d . . . H6 H 0.6118 0.4971 0.0018 0.050 Uiso 1 1 calc R . . C7 C 0.7048(8) 0.6349(8) 0.0141(5) 0.040(3) Uani 1 1 d . . . H7 H 0.6752 0.6581 -0.0090 0.048 Uiso 1 1 calc R . . C8 C 0.6574(7) 0.4009(7) 0.0704(5) 0.032(2) Uani 1 1 d . . . C9 C 0.7067(10) 0.3533(5) 0.0833 0.032(3) Uani 1 2 d S . . H9 H 0.7720 0.3860 0.0833 0.039 Uiso 1 2 calc SR . . C10 C 0.5613(8) 0.3497(8) 0.0691(6) 0.040(3) Uani 1 1 d . . . H10 H 0.5285 0.3795 0.0581 0.048 Uiso 1 1 calc R . . C11 C 0.5108(11) 0.2554(6) 0.0833 0.041(4) Uani 1 2 d S . . C12 C 0.4055(11) 0.2027(6) 0.0833 0.043(4) Uani 1 2 d S . . C13 C 0.3563(11) 0.2213(9) 0.0426(7) 0.059(4) Uani 1 1 d . . . H13 H 0.3889 0.2658 0.0148 0.071 Uiso 1 1 calc R . . C14 C 0.2594(11) 0.1741(9) 0.0430(6) 0.058(4) Uani 1 1 d . . . H14 H 0.2271 0.1884 0.0163 0.070 Uiso 1 1 calc R . . C15 C 0.2095(11) 0.1048(6) 0.0833 0.035(4) Uani 1 2 d S . . C16 C 0.1041(11) 0.0521(5) 0.0833 0.030(3) Uani 1 2 d S . . O1 O 0.8914(5) 0.8584(5) 0.0688(3) 0.0289(15) Uani 1 1 d . . . O2 O 0.7900(7) 0.8305(6) 0.0016(5) 0.069(3) Uani 1 1 d . . . O3 O 0.0642(5) 0.0705(5) 0.0451(3) 0.0402(18) Uani 1 1 d . . . O1W O 0.7649(8) 1.0000 0.0000 0.053(3) Uani 1 2 d S . . C17 C 0.917(2) 0.404(2) 0.1948(15) 0.219(19) Uiso 1 1 d D . . C18 C 0.765(3) 0.323(3) 0.250(2) 0.29(3) Uiso 1 1 d D . . C19 C 0.876(3) 0.256(3) 0.248(2) 0.28(2) Uiso 1 1 d D . . O4 O 0.981(4) 0.414(4) 0.158(2) 0.29(3) Uiso 0.50 1 d PD A 1 O4' O 0.899(2) 0.461(2) 0.1681(13) 0.137(11) Uiso 0.50 1 d PD A 2 N1 N 0.850(2) 0.324(2) 0.2328(14) 0.241(17) Uiso 1 1 d D A . 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 Pr1 0.0152(3) 0.0152(4) 0.0332(4) -0.0026(3) -0.00132(16) 0.00760(18) C1 0.022(5) 0.023(5) 0.051(6) -0.001(5) 0.010(5) 0.012(4) C2 0.025(5) 0.024(5) 0.039(6) -0.001(4) 0.003(4) 0.014(4) C3 0.023(5) 0.020(5) 0.043(6) 0.007(4) 0.001(5) 0.012(4) C4 0.017(5) 0.021(5) 0.047(6) 0.000(5) 0.004(4) 0.007(4) C5 0.021(5) 0.020(5) 0.054(7) 0.003(4) 0.004(5) 0.012(4) C6 0.043(7) 0.033(6) 0.057(7) 0.018(5) 0.019(6) 0.025(6) C7 0.038(6) 0.030(6) 0.059(8) 0.007(5) 0.020(5) 0.023(5) C8 0.020(5) 0.023(5) 0.052(6) 0.001(4) 0.006(5) 0.010(4) C9 0.019(7) 0.023(6) 0.054(9) 0.000(6) 0.000 0.009(4) C10 0.019(5) 0.022(5) 0.077(8) 0.003(6) 0.007(6) 0.008(4) C11 0.024(8) 0.017(5) 0.086(13) 0.000(7) 0.000 0.012(4) C12 0.022(8) 0.024(6) 0.081(14) 0.000(8) 0.000 0.011(4) C13 0.061(9) 0.021(6) 0.087(11) -0.003(7) 0.022(8) 0.015(6) C14 0.070(10) 0.028(7) 0.070(9) -0.007(7) 0.017(7) 0.019(7) C15 0.035(8) 0.023(6) 0.050(9) 0.000(5) 0.000 0.017(4) C16 0.032(8) 0.017(4) 0.045(8) 0.000(5) 0.000 0.016(4) O1 0.024(3) 0.032(4) 0.036(3) -0.004(3) -0.001(3) 0.019(3) O2 0.074(7) 0.048(5) 0.111(8) 0.037(6) 0.063(7) 0.050(5) O3 0.038(4) 0.022(4) 0.056(4) 0.004(3) 0.012(3) 0.012(3) O1W 0.051(5) 0.051(7) 0.058(7) 0.020(8) 0.010(4) 0.025(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 Pr1 O3 2.371(8) 1_665 ? Pr1 O3 2.371(8) 8_665 ? Pr1 O1 2.468(7) 5_564 ? Pr1 O1 2.468(7) 12_565 ? Pr1 O1W 2.478(12) . ? Pr1 O2 2.505(10) 8_675 ? Pr1 O2 2.505(10) . ? Pr1 O1 2.707(7) 8_675 ? Pr1 O1 2.707(7) . ? Pr1 C1 2.970(10) 8_675 ? Pr1 C1 2.970(10) . ? C1 O2 1.258(14) . ? C1 O1 1.261(13) . ? C1 C2 1.513(14) . ? C2 C3 1.376(15) . ? C2 C7 1.400(16) . ? C3 C4 1.372(14) . ? C4 C5 1.424(15) . ? C5 C6 1.379(16) . ? C5 C8 1.470(13) . ? C6 C7 1.401(16) . ? C8 C10 1.370(14) . ? C8 C9 1.412(12) . ? C9 C8 1.412(12) 12 ? C10 C11 1.386(13) . ? C11 C10 1.386(13) 12 ? C11 C12 1.50(2) . ? C12 C13 1.390(18) . ? C12 C13 1.390(18) 12 ? C13 C14 1.38(2) . ? C14 C15 1.399(16) . ? C15 C14 1.399(16) 12 ? C15 C16 1.50(2) . ? C16 O3 1.245(11) . ? C16 O3 1.245(11) 12 ? O1 Pr1 2.468(7) 6_655 ? O3 Pr1 2.371(8) 1_445 ? C17 O4' 1.266(10) . ? C17 O4 1.309(11) . ? C17 N1 1.516(9) . ? C18 N1 1.450(9) . ? C19 N1 1.428(9) . ? 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 O3 Pr1 O3 76.5(4) 1_665 8_665 ? O3 Pr1 O1 136.1(3) 1_665 5_564 ? O3 Pr1 O1 72.9(2) 8_665 5_564 ? O3 Pr1 O1 72.9(2) 1_665 12_565 ? O3 Pr1 O1 136.1(3) 8_665 12_565 ? O1 Pr1 O1 148.5(3) 5_564 12_565 ? O3 Pr1 O1W 141.7(2) 1_665 . ? O3 Pr1 O1W 141.7(2) 8_665 . ? O1 Pr1 O1W 74.24(17) 5_564 . ? O1 Pr1 O1W 74.24(17) 12_565 . ? O3 Pr1 O2 79.0(3) 1_665 8_675 ? O3 Pr1 O2 127.7(3) 8_665 8_675 ? O1 Pr1 O2 95.5(3) 5_564 8_675 ? O1 Pr1 O2 76.0(3) 12_565 8_675 ? O1W Pr1 O2 74.4(2) . 8_675 ? O3 Pr1 O2 127.7(3) 1_665 . ? O3 Pr1 O2 79.0(3) 8_665 . ? O1 Pr1 O2 76.0(3) 5_564 . ? O1 Pr1 O2 95.5(3) 12_565 . ? O1W Pr1 O2 74.4(2) . . ? O2 Pr1 O2 148.9(4) 8_675 . ? O3 Pr1 O1 74.7(2) 1_665 8_675 ? O3 Pr1 O1 79.7(2) 8_665 8_675 ? O1 Pr1 O1 69.5(3) 5_564 8_675 ? O1 Pr1 O1 120.3(2) 12_565 8_675 ? O1W Pr1 O1 106.43(15) . 8_675 ? O2 Pr1 O1 49.4(3) 8_675 8_675 ? O2 Pr1 O1 143.4(3) . 8_675 ? O3 Pr1 O1 79.7(2) 1_665 . ? O3 Pr1 O1 74.7(2) 8_665 . ? O1 Pr1 O1 120.3(2) 5_564 . ? O1 Pr1 O1 69.5(3) 12_565 . ? O1W Pr1 O1 106.43(15) . . ? O2 Pr1 O1 143.4(3) 8_675 . ? O2 Pr1 O1 49.4(3) . . ? O1 Pr1 O1 147.1(3) 8_675 . ? O3 Pr1 C1 72.0(3) 1_665 8_675 ? O3 Pr1 C1 103.1(3) 8_665 8_675 ? O1 Pr1 C1 85.1(3) 5_564 8_675 ? O1 Pr1 C1 96.6(3) 12_565 8_675 ? O1W Pr1 C1 93.0(2) . 8_675 ? O2 Pr1 C1 24.7(3) 8_675 8_675 ? O2 Pr1 C1 159.5(3) . 8_675 ? O1 Pr1 C1 25.1(3) 8_675 8_675 ? O1 Pr1 C1 151.1(2) . 8_675 ? O3 Pr1 C1 103.1(3) 1_665 . ? O3 Pr1 C1 72.0(3) 8_665 . ? O1 Pr1 C1 96.6(3) 5_564 . ? O1 Pr1 C1 85.1(3) 12_565 . ? O1W Pr1 C1 93.0(2) . . ? O2 Pr1 C1 159.5(3) 8_675 . ? O2 Pr1 C1 24.7(3) . . ? O1 Pr1 C1 151.1(2) 8_675 . ? O1 Pr1 C1 25.1(3) . . ? C1 Pr1 C1 174.0(4) 8_675 . ? O2 C1 O1 120.3(10) . . ? O2 C1 C2 118.7(10) . . ? O1 C1 C2 121.0(10) . . ? O2 C1 Pr1 56.5(6) . . ? O1 C1 Pr1 65.7(5) . . ? C2 C1 Pr1 165.5(8) . . ? C3 C2 C7 119.7(10) . . ? C3 C2 C1 121.3(9) . . ? C7 C2 C1 119.0(10) . . ? C4 C3 C2 120.6(10) . . ? C3 C4 C5 121.3(10) . . ? C6 C5 C4 117.2(10) . . ? C6 C5 C8 120.8(10) . . ? C4 C5 C8 121.7(10) . . ? C5 C6 C7 121.8(12) . . ? C2 C7 C6 119.3(11) . . ? C10 C8 C9 118.0(10) . . ? C10 C8 C5 120.2(10) . . ? C9 C8 C5 121.8(9) . . ? C8 C9 C8 120.5(13) . 12 ? C8 C10 C11 122.9(11) . . ? C10 C11 C10 117.5(15) . 12 ? C10 C11 C12 121.2(7) . . ? C10 C11 C12 121.2(7) 12 . ? C13 C12 C13 119.6(17) . 12 ? C13 C12 C11 120.2(8) . . ? C13 C12 C11 120.2(8) 12 . ? C14 C13 C12 120.4(14) . . ? C13 C14 C15 120.3(16) . . ? C14 C15 C14 119.0(19) . 12 ? C14 C15 C16 120.5(9) . . ? C14 C15 C16 120.5(9) 12 . ? O3 C16 O3 125.7(14) . 12 ? O3 C16 C15 117.1(7) . . ? O3 C16 C15 117.1(7) 12 . ? C1 O1 Pr1 139.3(7) . 6_655 ? C1 O1 Pr1 89.2(6) . . ? Pr1 O1 Pr1 108.4(3) 6_655 . ? C1 O2 Pr1 98.8(8) . . ? C16 O3 Pr1 138.6(8) . 1_445 ? O4' C17 O4 92(3) . . ? O4' C17 N1 127.6(19) . . ? O4 C17 N1 133(2) . . ? C19 N1 C18 124.7(9) . . ? C19 N1 C17 118.3(9) . . ? C18 N1 C17 117.0(8) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.956 _refine_diff_density_min -2.229 _refine_diff_density_rms 0.289