# 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 _publ_contact_author_email rzou@pku.edu.c _publ_contact_author_name 'Ruqiang Zou' loop_ _publ_author_name 'Zhongjun Lin' 'Jie Liang' 'Wei Xia' 'Ruqiang Zou' data_1-squeeze _database_code_depnum_ccdc_archive 'CCDC 825106' #TrackingRef '1-SQUEEZE.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H17 Ce O7' _chemical_formula_weight 593.53 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' Ce Ce -0.2486 2.6331 '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' H H 0.0000 0.0000 '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' 'x-y, x, z+1/6' '-y, x-y, z+1/3' '-x, -y, z+1/2' '-x+y, -x, z+2/3' 'y, -x+y, z+5/6' '-y, -x, -z+5/6' 'x-y, -y, -z' 'x, x-y, -z+1/6' 'y, x, -z+1/3' '-x+y, y, -z+1/2' '-x, -x+y, -z+2/3' _cell_length_a 16.5126(7) _cell_length_b 16.5126(7) _cell_length_c 24.5098(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5787.6(5) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7635 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.45 _exptl_crystal_description olive _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.02 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1758 _exptl_absorpt_coefficient_mu 1.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_T_max 0.824 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 14377 _diffrn_reflns_av_R_equivalents 0.0893 _diffrn_reflns_av_sigmaI/netI 0.0796 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.19 _reflns_number_total 3481 _reflns_number_gt 2916 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_reduction SAINT-Plus _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Sheldrick, 1998)' _computing_publication_material XP _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^)+(0.0882P)^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 0.000(1) _refine_ls_number_reflns 3481 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0652 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1479 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 Ce1 Ce 1.07705(4) 1.0000 1.0000 0.0219(2) Uani 1 2 d S . . C1 C 0.9715(5) 0.8033(5) 0.9600(3) 0.0295(19) Uani 1 1 d . . . C2 C 0.9037(6) 0.6982(6) 0.9534(3) 0.031(2) Uani 1 1 d . . . C3 C 0.9267(7) 0.6381(6) 0.9798(4) 0.044(2) Uani 1 1 d . . . H3 H 0.9782 0.6616 1.0029 0.053 Uiso 1 1 calc R . . C4 C 0.8707(7) 0.5405(7) 0.9711(4) 0.054(3) Uani 1 1 d . . . H4 H 0.8865 0.4997 0.9879 0.065 Uiso 1 1 calc R . . C5 C 0.7930(6) 0.5054(6) 0.9380(3) 0.0342(19) Uani 1 1 d . . . C6 C 0.7713(6) 0.5680(6) 0.9129(4) 0.037(2) Uani 1 1 d . . . H6 H 0.7188 0.5446 0.8905 0.045 Uiso 1 1 calc R . . C7 C 0.8267(7) 0.6662(6) 0.9204(3) 0.041(2) Uani 1 1 d . . . H7 H 0.8114 0.7073 0.9035 0.049 Uiso 1 1 calc R . . C8 C 0.7408(6) 0.4043(6) 0.9272(3) 0.0348(19) Uani 1 1 d . . . C9 C 0.6457(5) 0.3543(5) 0.9167 0.040(3) Uani 1 2 d S . . H9 H 0.6132 0.3868 0.9167 0.047 Uiso 1 2 calc SR . . C10 C 0.7866(7) 0.3534(7) 0.9273(4) 0.045(2) Uani 1 1 d . . . H10 H 0.8503 0.3844 0.9349 0.054 Uiso 1 1 calc R . . C11 C 0.7419(5) 0.2581(5) 0.9167 0.044(3) Uani 1 2 d S . . C12 C 0.7938(5) 0.2062(5) 0.9167 0.054(4) Uani 1 2 d S . . C13 C 0.8623(9) 0.2243(8) 0.9556(5) 0.068(3) Uani 1 1 d . . . H13 H 0.8752 0.2686 0.9826 0.081 Uiso 1 1 calc R . . C14 C 0.9106(9) 0.1771(9) 0.9540(4) 0.069(3) Uani 1 1 d . . . H14 H 0.9581 0.1924 0.9793 0.083 Uiso 1 1 calc R . . C15 C 0.8919(4) 0.1081(4) 0.9167 0.034(3) Uani 1 2 d S . . C16 C 0.9431(4) 0.0569(4) 0.9167 0.039(3) Uani 1 2 d S . . O1 O 1.0323(5) 0.8303(4) 0.9959(3) 0.057(2) Uani 1 1 d . . . O2 O 0.9622(4) 0.8608(4) 0.9290(2) 0.0307(13) Uani 1 1 d . . . O3 O 0.9990(5) 0.0718(5) 0.9547(2) 0.0489(14) Uani 1 1 d . . . 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 Ce1 0.0175(3) 0.0166(3) 0.0313(3) -0.0039(3) -0.00194(14) 0.00831(17) C1 0.017(4) 0.015(4) 0.045(4) -0.008(4) 0.009(4) -0.001(3) C2 0.026(5) 0.027(4) 0.038(4) -0.004(3) -0.003(3) 0.013(4) C3 0.040(5) 0.029(5) 0.062(5) -0.005(4) -0.023(5) 0.016(5) C4 0.039(6) 0.022(5) 0.097(7) 0.001(5) -0.025(5) 0.013(5) C5 0.029(5) 0.018(4) 0.055(5) -0.003(3) -0.007(4) 0.012(4) C6 0.027(5) 0.024(5) 0.056(5) -0.008(4) -0.010(4) 0.009(4) C7 0.039(6) 0.033(5) 0.048(4) 0.003(4) -0.011(4) 0.016(4) C8 0.030(5) 0.018(4) 0.058(5) -0.001(4) -0.004(4) 0.013(4) C9 0.028(5) 0.028(5) 0.061(7) 0.000(5) 0.000(5) 0.012(6) C10 0.024(5) 0.026(5) 0.085(6) -0.009(5) -0.006(5) 0.012(4) C11 0.026(5) 0.026(5) 0.089(10) -0.011(6) -0.011(6) 0.020(6) C12 0.029(6) 0.029(6) 0.107(12) -0.011(7) -0.011(7) 0.017(7) C13 0.070(8) 0.045(7) 0.118(9) -0.034(7) -0.038(7) 0.050(6) C14 0.068(8) 0.091(10) 0.070(6) -0.017(7) -0.030(7) 0.057(8) C15 0.031(5) 0.031(5) 0.045(6) -0.008(5) -0.008(5) 0.021(6) C16 0.045(6) 0.045(6) 0.037(6) 0.001(5) 0.001(5) 0.029(7) O1 0.078(5) 0.020(3) 0.075(4) -0.023(3) -0.051(4) 0.026(3) O2 0.041(3) 0.013(3) 0.038(2) 0.001(2) -0.001(2) 0.013(3) O3 0.052(4) 0.056(4) 0.059(3) 0.001(3) -0.005(4) 0.042(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 Ce1 O3 2.414(6) 1_565 ? Ce1 O3 2.414(6) 8_567 ? Ce1 O2 2.511(5) 7_776 ? Ce1 O2 2.511(5) 2_655 ? Ce1 O1 2.517(6) 8_677 ? Ce1 O1 2.517(5) . ? Ce1 O2 2.747(5) . ? Ce1 O2 2.747(5) 8_677 ? Ce1 C1 2.981(7) . ? Ce1 C1 2.981(7) 8_677 ? C1 O1 1.239(10) . ? C1 O2 1.284(10) . ? C1 C2 1.533(11) . ? C2 C3 1.386(12) . ? C2 C7 1.371(12) . ? C3 C4 1.418(13) . ? C3 H3 0.9300 . ? C4 C5 1.376(12) . ? C4 H4 0.9300 . ? C5 C6 1.395(12) . ? C5 C8 1.471(11) . ? C6 C7 1.421(12) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C10 1.383(12) . ? C8 C9 1.384(10) . ? C9 C8 1.384(10) 7_666 ? C9 H9 0.9300 . ? C10 C11 1.387(11) . ? C10 H10 0.9300 . ? C11 C10 1.387(11) 7_666 ? C11 C12 1.485(19) . ? C12 C13 1.393(13) . ? C12 C13 1.393(13) 7_666 ? C13 C14 1.366(14) . ? C13 H13 0.9300 . ? C14 C15 1.371(13) . ? C14 H14 0.9300 . ? C15 C14 1.371(13) 7_666 ? C15 C16 1.466(17) . ? C16 O3 1.248(8) . ? C16 O3 1.248(8) 7_666 ? O2 Ce1 2.511(5) 6_564 ? O3 Ce1 2.414(6) 1_545 ? 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 Ce1 O3 77.6(4) 1_565 8_567 ? O3 Ce1 O2 72.59(19) 1_565 7_776 ? O3 Ce1 O2 137.96(19) 8_567 7_776 ? O3 Ce1 O2 137.96(19) 1_565 2_655 ? O3 Ce1 O2 72.59(19) 8_567 2_655 ? O2 Ce1 O2 146.9(2) 7_776 2_655 ? O3 Ce1 O1 79.2(3) 1_565 8_677 ? O3 Ce1 O1 126.7(2) 8_567 8_677 ? O2 Ce1 O1 75.82(19) 7_776 8_677 ? O2 Ce1 O1 95.5(2) 2_655 8_677 ? O3 Ce1 O1 126.7(2) 1_565 . ? O3 Ce1 O1 79.2(3) 8_567 . ? O2 Ce1 O1 95.5(2) 7_776 . ? O2 Ce1 O1 75.82(19) 2_655 . ? O1 Ce1 O1 149.5(3) 8_677 . ? O3 Ce1 O2 78.8(2) 1_565 . ? O3 Ce1 O2 76.75(19) 8_567 . ? O2 Ce1 O2 68.99(19) 7_776 . ? O2 Ce1 O2 120.87(16) 2_655 . ? O1 Ce1 O2 142.7(2) 8_677 . ? O1 Ce1 O2 49.29(17) . . ? O3 Ce1 O2 76.75(19) 1_565 8_677 ? O3 Ce1 O2 78.8(2) 8_567 8_677 ? O2 Ce1 O2 120.87(16) 7_776 8_677 ? O2 Ce1 O2 68.99(19) 2_655 8_677 ? O1 Ce1 O2 49.29(17) 8_677 8_677 ? O1 Ce1 O2 142.7(2) . 8_677 ? O2 Ce1 O2 148.5(2) . 8_677 ? O3 Ce1 C1 102.7(2) 1_565 . ? O3 Ce1 C1 73.6(2) 8_567 . ? O2 Ce1 C1 84.68(19) 7_776 . ? O2 Ce1 C1 96.6(2) 2_655 . ? O1 Ce1 C1 158.93(19) 8_677 . ? O1 Ce1 C1 24.2(2) . . ? O2 Ce1 C1 25.5(2) . . ? O2 Ce1 C1 151.77(18) 8_677 . ? O3 Ce1 C1 73.6(2) 1_565 8_677 ? O3 Ce1 C1 102.7(2) 8_567 8_677 ? O2 Ce1 C1 96.6(2) 7_776 8_677 ? O2 Ce1 C1 84.68(19) 2_655 8_677 ? O1 Ce1 C1 24.2(2) 8_677 8_677 ? O1 Ce1 C1 158.93(19) . 8_677 ? O2 Ce1 C1 151.77(17) . 8_677 ? O2 Ce1 C1 25.5(2) 8_677 8_677 ? C1 Ce1 C1 175.4(3) . 8_677 ? O1 C1 O2 121.9(7) . . ? O1 C1 C2 119.0(8) . . ? O2 C1 C2 119.1(7) . . ? O1 C1 Ce1 56.4(4) . . ? O2 C1 Ce1 67.0(4) . . ? C2 C1 Ce1 165.2(5) . . ? C3 C2 C7 122.2(8) . . ? C3 C2 C1 117.1(7) . . ? C7 C2 C1 120.6(8) . . ? C2 C3 C4 119.1(8) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 120.5(8) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 118.7(8) . . ? C4 C5 C8 118.5(8) . . ? C6 C5 C8 122.6(8) . . ? C5 C6 C7 122.0(8) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C2 C7 C6 117.4(8) . . ? C2 C7 H7 121.3 . . ? C6 C7 H7 121.3 . . ? C10 C8 C9 116.0(8) . . ? C10 C8 C5 120.1(8) . . ? C9 C8 C5 123.9(8) . . ? C8 C9 C8 124.5(12) . 7_666 ? C8 C9 H9 117.7 . . ? C8 C9 H9 117.7 7_666 . ? C8 C10 C11 123.1(9) . . ? C8 C10 H10 118.5 . . ? C11 C10 H10 118.5 . . ? C10 C11 C10 117.3(12) . 7_666 ? C10 C11 C12 121.4(6) . . ? C10 C11 C12 121.4(6) 7_666 . ? C13 C12 C13 117.6(13) . 7_666 ? C13 C12 C11 121.2(7) . . ? C13 C12 C11 121.2(7) 7_666 . ? C14 C13 C12 120.1(11) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 122.6(10) . . ? C13 C14 H14 118.7 . . ? C15 C14 H14 118.7 . . ? C14 C15 C14 116.7(12) . 7_666 ? C14 C15 C16 121.6(6) . . ? C14 C15 C16 121.6(6) 7_666 . ? O3 C16 O3 123.9(12) . 7_666 ? O3 C16 C15 118.0(6) . . ? O3 C16 C15 118.0(6) 7_666 . ? C1 O1 Ce1 99.4(5) . . ? C1 O2 Ce1 139.3(5) . 6_564 ? C1 O2 Ce1 87.5(4) . . ? Ce1 O2 Ce1 108.86(18) 6_564 . ? C16 O3 Ce1 140.4(7) . 1_545 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.444 _refine_diff_density_min -0.587 _refine_diff_density_rms 0.130 # 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 -0.035 0.433 0.828 3096 661 ' ' _platon_squeeze_details ; END ; # Attachment '1.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 825107' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H17 Ce O7' _chemical_formula_weight 593.53 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' Ce Ce -0.2486 2.6331 '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' H H 0.0000 0.0000 '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' 'x-y, x, z+1/6' '-y, x-y, z+1/3' '-x, -y, z+1/2' '-x+y, -x, z+2/3' 'y, -x+y, z+5/6' '-y, -x, -z+5/6' 'x-y, -y, -z' 'x, x-y, -z+1/6' 'y, x, -z+1/3' '-x+y, y, -z+1/2' '-x, -x+y, -z+2/3' _cell_length_a 16.5126(7) _cell_length_b 16.5126(7) _cell_length_c 24.5098(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 5787.6(5) _cell_formula_units_Z 6 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7636 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.45 _exptl_crystal_description olive _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.022 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1758 _exptl_absorpt_coefficient_mu 1.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.748 _exptl_absorpt_correction_T_max 0.824 _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 14377 _diffrn_reflns_av_R_equivalents 0.0741 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.19 _reflns_number_total 3481 _reflns_number_gt 2935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'SAINT-Plus (Bruker, 2001)' _computing_data_reduction SAINT-Plus _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Sheldrick, 1998)' _computing_publication_material XP _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^)+(0.1304P)^2^+10.2062P] 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 0.000(1) _refine_ls_number_reflns 3481 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0794 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.2175 _refine_ls_wR_factor_gt 0.2041 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 Ce1 Ce 1.07702(5) 1.0000 1.0000 0.0217(3) Uani 1 2 d S . . C1 C 0.9703(7) 0.8037(7) 0.9602(4) 0.030(3) Uani 1 1 d . . . C2 C 0.9036(7) 0.6986(8) 0.9540(4) 0.030(3) Uani 1 1 d . . . C3 C 0.9261(10) 0.6379(9) 0.9802(5) 0.043(3) Uani 1 1 d . . . H3 H 0.9777 0.6610 1.0032 0.052 Uiso 1 1 calc R . . C4 C 0.8697(10) 0.5413(10) 0.9715(6) 0.054(4) Uani 1 1 d . . . H4 H 0.8851 0.5008 0.9890 0.064 Uiso 1 1 calc R . . C5 C 0.7938(9) 0.5053(8) 0.9385(5) 0.036(3) Uani 1 1 d . . . C6 C 0.7714(8) 0.5684(8) 0.9133(5) 0.035(3) Uani 1 1 d . . . H6 H 0.7189 0.5447 0.8909 0.041 Uiso 1 1 calc R . . C7 C 0.8251(9) 0.6652(8) 0.9207(5) 0.037(3) Uani 1 1 d . . . H7 H 0.8089 0.7058 0.9040 0.045 Uiso 1 1 calc R . . C8 C 0.7409(8) 0.4038(8) 0.9276(5) 0.036(3) Uani 1 1 d . . . C9 C 0.6454(6) 0.3546(6) 0.9167 0.035(4) Uani 1 2 d S . . H9 H 0.6128 0.3872 0.9167 0.042 Uiso 1 2 calc SR . . C10 C 0.7849(9) 0.3529(9) 0.9282(6) 0.046(3) Uani 1 1 d . . . H10 H 0.8482 0.3835 0.9369 0.056 Uiso 1 1 calc R . . C11 C 0.7414(6) 0.2586(6) 0.9167 0.050(5) Uani 1 2 d S . . C12 C 0.7940(7) 0.2060(7) 0.9167 0.054(5) Uani 1 2 d S . . C13 C 0.8617(12) 0.2235(11) 0.9559(7) 0.068(5) Uani 1 1 d . . . H13 H 0.8742 0.2676 0.9830 0.081 Uiso 1 1 calc R . . C14 C 0.9089(12) 0.1776(12) 0.9548(6) 0.065(4) Uani 1 1 d . . . H14 H 0.9555 0.1923 0.9806 0.077 Uiso 1 1 calc R . . C15 C 0.8911(6) 0.1089(6) 0.9167 0.038(4) Uani 1 2 d S . . C16 C 0.9439(6) 0.0561(6) 0.9167 0.037(4) Uani 1 2 d S . . O1 O 1.0315(7) 0.8314(5) 0.9964(4) 0.058(3) Uani 1 1 d . . . O2 O 0.9624(5) 0.8612(5) 0.9290(3) 0.0301(17) Uani 1 1 d . . . O3 O 0.9988(8) 0.0708(7) 0.9548(3) 0.050(2) Uani 1 1 d . . . O1W O 1.2308(9) 1.0000 1.0000 0.065(4) 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 Ce1 0.0172(3) 0.0167(5) 0.0311(4) -0.0036(4) -0.00181(18) 0.0083(2) C1 0.023(6) 0.014(5) 0.045(6) -0.004(5) 0.010(5) 0.003(4) C2 0.021(6) 0.025(6) 0.041(5) -0.007(5) -0.006(4) 0.010(5) C3 0.042(7) 0.028(7) 0.058(7) -0.002(5) -0.021(6) 0.016(6) C4 0.044(9) 0.033(7) 0.085(9) -0.003(7) -0.027(7) 0.019(7) C5 0.028(7) 0.021(6) 0.059(7) -0.004(5) -0.010(5) 0.012(6) C6 0.026(6) 0.026(6) 0.049(6) -0.007(5) -0.009(5) 0.011(5) C7 0.035(7) 0.023(6) 0.049(6) 0.003(5) -0.009(5) 0.012(5) C8 0.029(6) 0.016(6) 0.064(7) -0.006(5) -0.007(6) 0.012(5) C9 0.022(6) 0.022(6) 0.059(9) -0.002(6) -0.002(6) 0.009(7) C10 0.017(6) 0.027(7) 0.093(9) -0.012(7) -0.013(6) 0.009(6) C11 0.027(7) 0.027(7) 0.107(15) -0.014(9) -0.014(9) 0.021(9) C12 0.023(7) 0.023(7) 0.114(17) -0.005(9) -0.005(9) 0.009(8) C13 0.068(11) 0.050(9) 0.115(12) -0.039(9) -0.044(10) 0.052(9) C14 0.068(11) 0.071(11) 0.072(9) -0.021(9) -0.032(9) 0.047(9) C15 0.033(7) 0.033(7) 0.057(10) -0.008(7) -0.008(7) 0.024(8) C16 0.041(8) 0.041(8) 0.038(8) 0.000(7) 0.000(7) 0.026(9) O1 0.073(7) 0.014(4) 0.081(6) -0.019(4) -0.052(6) 0.017(4) O2 0.038(4) 0.010(4) 0.040(3) 0.001(3) -0.001(3) 0.010(3) O3 0.053(5) 0.059(6) 0.061(5) 0.001(5) -0.005(5) 0.044(6) O1W 0.062(7) 0.075(10) 0.063(7) 0.028(9) 0.014(5) 0.037(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 Ce1 O3 2.403(8) 8_567 ? Ce1 O3 2.403(8) 1_565 ? Ce1 O1 2.497(8) 8_677 ? Ce1 O1 2.497(8) . ? Ce1 O2 2.509(7) 7_776 ? Ce1 O2 2.509(7) 2_655 ? Ce1 O1W 2.539(15) . ? Ce1 O2 2.743(7) . ? Ce1 O2 2.743(7) 8_677 ? Ce1 C1 2.975(10) 8_677 ? Ce1 C1 2.975(10) . ? C1 O1 1.248(13) . ? C1 O2 1.274(13) . ? C1 C2 1.529(15) . ? C2 C3 1.388(16) . ? C2 C7 1.391(15) . ? C3 C4 1.404(18) . ? C3 H3 0.9300 . ? C4 C5 1.355(17) . ? C4 H4 0.9300 . ? C5 C6 1.411(16) . ? C5 C8 1.477(15) . ? C6 C7 1.400(16) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C10 1.358(16) . ? C8 C9 1.393(14) . ? C9 C8 1.393(14) 7_666 ? C9 H9 0.9300 . ? C10 C11 1.379(15) . ? C10 H10 0.9300 . ? C11 C10 1.379(15) 7_666 ? C11 C12 1.50(3) . ? C12 C13 1.392(17) . ? C12 C13 1.392(17) 7_666 ? C13 C14 1.332(19) . ? C13 H13 0.9300 . ? C14 C15 1.382(17) . ? C14 H14 0.9300 . ? C15 C14 1.382(17) 7_666 ? C15 C16 1.51(2) . ? C16 O3 1.239(12) . ? C16 O3 1.239(12) 7_666 ? O2 Ce1 2.509(7) 6_564 ? O3 Ce1 2.403(8) 1_545 ? 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 Ce1 O3 77.3(5) 8_567 1_565 ? O3 Ce1 O1 126.2(3) 8_567 8_677 ? O3 Ce1 O1 79.0(4) 1_565 8_677 ? O3 Ce1 O1 79.0(4) 8_567 . ? O3 Ce1 O1 126.2(3) 1_565 . ? O1 Ce1 O1 150.2(5) 8_677 . ? O3 Ce1 O2 137.9(3) 8_567 7_776 ? O3 Ce1 O2 72.5(3) 1_565 7_776 ? O1 Ce1 O2 75.8(3) 8_677 7_776 ? O1 Ce1 O2 95.8(3) . 7_776 ? O3 Ce1 O2 72.5(3) 8_567 2_655 ? O3 Ce1 O2 137.9(3) 1_565 2_655 ? O1 Ce1 O2 95.8(3) 8_677 2_655 ? O1 Ce1 O2 75.8(3) . 2_655 ? O2 Ce1 O2 147.1(3) 7_776 2_655 ? O3 Ce1 O1W 141.4(2) 8_567 . ? O3 Ce1 O1W 141.4(3) 1_565 . ? O1 Ce1 O1W 75.1(2) 8_677 . ? O1 Ce1 O1W 75.1(2) . . ? O2 Ce1 O1W 73.56(16) 7_776 . ? O2 Ce1 O1W 73.56(16) 2_655 . ? O3 Ce1 O2 77.0(3) 8_567 . ? O3 Ce1 O2 78.5(3) 1_565 . ? O1 Ce1 O2 142.3(3) 8_677 . ? O1 Ce1 O2 49.3(2) . . ? O2 Ce1 O2 68.8(3) 7_776 . ? O2 Ce1 O2 121.0(2) 2_655 . ? O1W Ce1 O2 105.79(16) . . ? O3 Ce1 O2 78.5(3) 8_567 8_677 ? O3 Ce1 O2 77.0(3) 1_565 8_677 ? O1 Ce1 O2 49.3(2) 8_677 8_677 ? O1 Ce1 O2 142.3(3) . 8_677 ? O2 Ce1 O2 121.0(2) 7_776 8_677 ? O2 Ce1 O2 68.8(3) 2_655 8_677 ? O1W Ce1 O2 105.79(16) . 8_677 ? O2 Ce1 O2 148.4(3) . 8_677 ? O3 Ce1 C1 102.1(3) 8_567 8_677 ? O3 Ce1 C1 73.5(3) 1_565 8_677 ? O1 Ce1 C1 24.4(3) 8_677 8_677 ? O1 Ce1 C1 159.2(3) . 8_677 ? O2 Ce1 C1 96.8(3) 7_776 8_677 ? O2 Ce1 C1 84.8(3) 2_655 8_677 ? O1W Ce1 C1 92.7(2) . 8_677 ? O2 Ce1 C1 151.4(2) . 8_677 ? O2 Ce1 C1 25.3(3) 8_677 8_677 ? O3 Ce1 C1 73.5(3) 8_567 . ? O3 Ce1 C1 102.1(3) 1_565 . ? O1 Ce1 C1 159.2(3) 8_677 . ? O1 Ce1 C1 24.4(3) . . ? O2 Ce1 C1 84.8(3) 7_776 . ? O2 Ce1 C1 96.8(3) 2_655 . ? O1W Ce1 C1 92.7(2) . . ? O2 Ce1 C1 25.3(3) . . ? O2 Ce1 C1 151.4(2) 8_677 . ? C1 Ce1 C1 174.5(4) 8_677 . ? O1 C1 O2 121.3(9) . . ? O1 C1 C2 118.5(10) . . ? O2 C1 C2 120.2(10) . . ? O1 C1 Ce1 55.8(5) . . ? O2 C1 Ce1 67.1(5) . . ? C2 C1 Ce1 165.4(7) . . ? C3 C2 C7 121.2(11) . . ? C3 C2 C1 118.2(10) . . ? C7 C2 C1 120.5(10) . . ? C2 C3 C4 119.0(11) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 122.1(12) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 117.7(11) . . ? C4 C5 C8 119.9(11) . . ? C6 C5 C8 122.3(11) . . ? C7 C6 C5 122.4(11) . . ? C7 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? C2 C7 C6 117.5(11) . . ? C2 C7 H7 121.3 . . ? C6 C7 H7 121.3 . . ? C10 C8 C9 116.3(11) . . ? C10 C8 C5 120.3(10) . . ? C9 C8 C5 123.4(11) . . ? C8 C9 C8 123.1(15) . 7_666 ? C8 C9 H9 118.5 . . ? C8 C9 H9 118.5 7_666 . ? C8 C10 C11 123.9(12) . . ? C8 C10 H10 118.0 . . ? C11 C10 H10 118.0 . . ? C10 C11 C10 116.4(16) . 7_666 ? C10 C11 C12 121.8(8) . . ? C10 C11 C12 121.8(8) 7_666 . ? C13 C12 C13 117.8(18) . 7_666 ? C13 C12 C11 121.1(9) . . ? C13 C12 C11 121.1(9) 7_666 . ? C14 C13 C12 120.4(15) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 122.4(14) . . ? C13 C14 H14 118.8 . . ? C15 C14 H14 118.8 . . ? C14 C15 C14 116.6(17) . 7_666 ? C14 C15 C16 121.7(8) . . ? C14 C15 C16 121.7(8) 7_666 . ? O3 C16 O3 124.7(16) . 7_666 ? O3 C16 C15 117.6(8) . . ? O3 C16 C15 117.6(8) 7_666 . ? C1 O1 Ce1 99.8(7) . . ? C1 O2 Ce1 140.0(7) . 6_564 ? C1 O2 Ce1 87.6(6) . . ? Ce1 O2 Ce1 109.0(2) 6_564 . ? C16 O3 Ce1 140.5(9) . 1_545 ? 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 O3 Ce1 C1 O1 -99.9(8) 8_567 . . . ? O3 Ce1 C1 O1 -172.6(8) 1_565 . . . ? O1 Ce1 C1 O1 96.5(15) 8_677 . . . ? O2 Ce1 C1 O1 116.5(8) 7_776 . . . ? O2 Ce1 C1 O1 -30.4(8) 2_655 . . . ? O1W Ce1 C1 O1 43.3(8) . . . . ? O2 Ce1 C1 O1 165.7(11) . . . . ? O2 Ce1 C1 O1 -87.7(10) 8_677 . . . ? C1 Ce1 C1 O1 -136.7(8) 8_677 . . . ? O3 Ce1 C1 O2 94.4(6) 8_567 . . . ? O3 Ce1 C1 O2 21.7(6) 1_565 . . . ? O1 Ce1 C1 O2 -69.2(12) 8_677 . . . ? O1 Ce1 C1 O2 -165.7(11) . . . . ? O2 Ce1 C1 O2 -49.2(5) 7_776 . . . ? O2 Ce1 C1 O2 163.9(6) 2_655 . . . ? O1W Ce1 C1 O2 -122.4(6) . . . . ? O2 Ce1 C1 O2 106.6(8) 8_677 . . . ? C1 Ce1 C1 O2 57.6(6) 8_677 . . . ? O3 Ce1 C1 C2 -28(3) 8_567 . . . ? O3 Ce1 C1 C2 -101(3) 1_565 . . . ? O1 Ce1 C1 C2 168(3) 8_677 . . . ? O1 Ce1 C1 C2 72(3) . . . . ? O2 Ce1 C1 C2 -172(3) 7_776 . . . ? O2 Ce1 C1 C2 41(3) 2_655 . . . ? O1W Ce1 C1 C2 115(3) . . . . ? O2 Ce1 C1 C2 -123(3) . . . . ? O2 Ce1 C1 C2 -16(4) 8_677 . . . ? C1 Ce1 C1 C2 -65(3) 8_677 . . . ? O1 C1 C2 C3 -13.8(16) . . . . ? O2 C1 C2 C3 166.6(11) . . . . ? Ce1 C1 C2 C3 -77(3) . . . . ? O1 C1 C2 C7 169.3(11) . . . . ? O2 C1 C2 C7 -10.3(16) . . . . ? Ce1 C1 C2 C7 106(3) . . . . ? C7 C2 C3 C4 1.9(19) . . . . ? C1 C2 C3 C4 -175.0(12) . . . . ? C2 C3 C4 C5 0(2) . . . . ? C3 C4 C5 C6 -1(2) . . . . ? C3 C4 C5 C8 175.6(13) . . . . ? C4 C5 C6 C7 1(2) . . . . ? C8 C5 C6 C7 -175.6(12) . . . . ? C3 C2 C7 C6 -2.0(18) . . . . ? C1 C2 C7 C6 174.8(11) . . . . ? C5 C6 C7 C2 0.6(19) . . . . ? C4 C5 C8 C10 -30(2) . . . . ? C6 C5 C8 C10 146.9(14) . . . . ? C4 C5 C8 C9 149.9(12) . . . . ? C6 C5 C8 C9 -33.6(18) . . . . ? C10 C8 C9 C8 -1.3(9) . . . 7_666 ? C5 C8 C9 C8 179.2(13) . . . 7_666 ? C9 C8 C10 C11 3(2) . . . . ? C5 C8 C10 C11 -177.8(11) . . . . ? C8 C10 C11 C10 -1.4(11) . . . 7_666 ? C8 C10 C11 C12 178.6(11) . . . . ? C10 C11 C12 C13 39.9(12) . . . . ? C10 C11 C12 C13 -140.1(12) 7_666 . . . ? C10 C11 C12 C13 -140.1(12) . . . 7_666 ? C10 C11 C12 C13 39.9(12) 7_666 . . 7_666 ? C13 C12 C13 C14 1.2(14) 7_666 . . . ? C11 C12 C13 C14 -178.8(13) . . . . ? C12 C13 C14 C15 -2(3) . . . . ? C13 C14 C15 C14 1.3(14) . . . 7_666 ? C13 C14 C15 C16 -178.7(14) . . . . ? C14 C15 C16 O3 5.8(11) . . . . ? C14 C15 C16 O3 -174.2(11) 7_666 . . . ? C14 C15 C16 O3 -174.2(11) . . . 7_666 ? C14 C15 C16 O3 5.8(11) 7_666 . . 7_666 ? O2 C1 O1 Ce1 15.4(12) . . . . ? C2 C1 O1 Ce1 -164.2(8) . . . . ? O3 Ce1 O1 C1 74.2(8) 8_567 . . . ? O3 Ce1 O1 C1 9.0(9) 1_565 . . . ? O1 Ce1 O1 C1 -134.8(8) 8_677 . . . ? O2 Ce1 O1 C1 -63.6(8) 7_776 . . . ? O2 Ce1 O1 C1 148.7(8) 2_655 . . . ? O1W Ce1 O1 C1 -134.8(8) . . . . ? O2 Ce1 O1 C1 -8.0(6) . . . . ? O2 Ce1 O1 C1 128.5(7) 8_677 . . . ? C1 Ce1 O1 C1 169.3(9) 8_677 . . . ? O1 C1 O2 Ce1 103.4(12) . . . 6_564 ? C2 C1 O2 Ce1 -77.0(13) . . . 6_564 ? Ce1 C1 O2 Ce1 117.3(9) . . . 6_564 ? O1 C1 O2 Ce1 -13.8(11) . . . . ? C2 C1 O2 Ce1 165.8(9) . . . . ? O3 Ce1 O2 C1 -78.9(6) 8_567 . . . ? O3 Ce1 O2 C1 -158.3(6) 1_565 . . . ? O1 Ce1 O2 C1 147.2(6) 8_677 . . . ? O1 Ce1 O2 C1 7.7(6) . . . . ? O2 Ce1 O2 C1 126.1(5) 7_776 . . . ? O2 Ce1 O2 C1 -18.8(7) 2_655 . . . ? O1W Ce1 O2 C1 61.2(6) . . . . ? O2 Ce1 O2 C1 -118.8(6) 8_677 . . . ? C1 Ce1 O2 C1 -170.3(8) 8_677 . . . ? O3 Ce1 O2 Ce1 138.2(4) 8_567 . . 6_564 ? O3 Ce1 O2 Ce1 58.8(3) 1_565 . . 6_564 ? O1 Ce1 O2 Ce1 4.3(6) 8_677 . . 6_564 ? O1 Ce1 O2 Ce1 -135.1(5) . . . 6_564 ? O2 Ce1 O2 Ce1 -16.7(4) 7_776 . . 6_564 ? O2 Ce1 O2 Ce1 -161.64(13) 2_655 . . 6_564 ? O1W Ce1 O2 Ce1 -81.6(2) . . . 6_564 ? O2 Ce1 O2 Ce1 98.4(2) 8_677 . . 6_564 ? C1 Ce1 O2 Ce1 46.9(7) 8_677 . . 6_564 ? C1 Ce1 O2 Ce1 -142.8(7) . . . 6_564 ? O3 C16 O3 Ce1 -20.2(8) 7_666 . . 1_545 ? C15 C16 O3 Ce1 159.8(8) . . . 1_545 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.19 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.571 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.196