# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxs _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H11 Dy O9' _chemical_formula_weight 569.80 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' Dy Dy -0.1892 4.4098 '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 ? _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 29.642(4) _cell_length_b 9.0327(12) _cell_length_c 16.378(2) _cell_angle_alpha 90.00 _cell_angle_beta 113.031(3) _cell_angle_gamma 90.00 _cell_volume 4035.7(9) _cell_formula_units_Z 8 _cell_measurement_temperature 386(2) _cell_measurement_reflns_used 5980 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 25.01 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.876 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2200 _exptl_absorpt_coefficient_mu 3.755 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6215 _exptl_absorpt_correction_T_max 0.7052 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 386(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku 002 Saturn 944 area detector' _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 12489 _diffrn_reflns_av_R_equivalents 0.0566 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3557 _reflns_number_gt 3050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert 2.0 r4 SHELXTL (Rigaku, 2009)' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Rigaku SHELXTL(Sheldrick, 1990)' _computing_publication_material 'Rigaku SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0271P)^2^+9.4249P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3557 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0782 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 O7 O 0.93907(12) 0.4954(4) 1.0550(2) 0.0358(9) Uani 1 1 d . . . O2 O 0.54127(12) 0.0558(4) 0.6038(3) 0.0381(10) Uani 1 1 d . . . O1 O 0.55436(13) 0.2649(4) 0.5456(2) 0.0358(10) Uani 1 1 d . . . C1 C 0.56861(19) 0.1616(6) 0.6027(3) 0.0252(12) Uani 1 1 d . . . O3 O 0.56325(13) 0.7849(4) 0.7259(2) 0.0325(9) Uani 1 1 d . . . O4 O 0.54379(12) 0.7454(4) 0.8406(2) 0.0304(9) Uani 1 1 d . . . C2 C 0.57300(18) 0.7412(5) 0.8039(3) 0.0212(11) Uani 1 1 d . . . C16 C 0.78931(17) 0.4474(5) 0.9782(3) 0.0211(11) Uani 1 1 d . . . Dy1 Dy 0.997394(8) 0.33138(3) 0.910774(16) 0.02325(10) Uani 1 1 d . . . O6 O 0.76875(12) 0.1324(4) 0.8267(2) 0.0259(8) Uani 1 1 d . . . C12 C 0.71892(18) 0.1482(5) 0.7752(3) 0.0215(11) Uani 1 1 d . . . C15 C 0.76505(18) 0.3363(5) 0.9192(3) 0.0214(11) Uani 1 1 d . . . H15 H 0.7314 0.3243 0.9010 0.026 Uiso 1 1 calc R . . C6 C 0.71717(18) 0.5852(5) 0.9552(3) 0.0231(12) Uani 1 1 d . . . O10 O 0.98497(16) 0.0597(4) 0.9059(3) 0.0501(12) Uani 1 1 d . . . O5 O 0.76445(12) 0.5437(4) 1.0104(2) 0.0312(9) Uani 1 1 d . . . O8 O 0.94154(13) 0.2984(4) 0.9743(3) 0.0330(9) Uani 1 1 d . . . C3 C 0.62334(18) 0.6834(5) 0.8552(3) 0.0197(11) Uani 1 1 d . . . C4 C 0.63727(19) 0.6478(6) 0.9447(3) 0.0269(12) Uani 1 1 d . . . H4 H 0.6148 0.6571 0.9711 0.032 Uiso 1 1 calc R . . C9 C 0.62078(18) 0.1624(5) 0.6679(3) 0.0212(11) Uani 1 1 d . . . C8 C 0.65731(19) 0.6686(5) 0.8177(3) 0.0244(12) Uani 1 1 d . . . H8 H 0.6484 0.6910 0.7580 0.029 Uiso 1 1 calc R . . C18 C 0.86553(18) 0.3651(5) 0.9784(3) 0.0209(11) Uani 1 1 d . . . C13 C 0.68892(18) 0.0330(5) 0.7752(3) 0.0275(12) Uani 1 1 d . . . H13 H 0.7015 -0.0491 0.8112 0.033 Uiso 1 1 calc R . . C17 C 0.83939(17) 0.4616(5) 1.0087(3) 0.0243(12) Uani 1 1 d . . . H17 H 0.8555 0.5353 1.0493 0.029 Uiso 1 1 calc R . . C20 C 0.79149(17) 0.2439(5) 0.8879(3) 0.0194(11) Uani 1 1 d . . . C7 C 0.70424(19) 0.6213(6) 0.8671(3) 0.0275(12) Uani 1 1 d . . . H7 H 0.7271 0.6137 0.8414 0.033 Uiso 1 1 calc R . . C11 C 0.70046(19) 0.2714(6) 0.7233(3) 0.0279(13) Uani 1 1 d . . . H11 H 0.7212 0.3490 0.7242 0.033 Uiso 1 1 calc R . . C19 C 0.84146(17) 0.2548(5) 0.9174(3) 0.0200(11) Uani 1 1 d . . . H19 H 0.8590 0.1896 0.8971 0.024 Uiso 1 1 calc R . . C14 C 0.63985(18) 0.0405(6) 0.7210(3) 0.0286(13) Uani 1 1 d . . . H14 H 0.6193 -0.0378 0.7202 0.034 Uiso 1 1 calc R . . C10 C 0.65138(19) 0.2797(6) 0.6702(3) 0.0265(12) Uani 1 1 d . . . H10 H 0.6388 0.3636 0.6360 0.032 Uiso 1 1 calc R . . C21 C 0.91975(18) 0.3868(6) 1.0055(4) 0.0261(12) Uani 1 1 d . . . C5 C 0.68427(18) 0.5988(6) 0.9945(3) 0.0251(12) Uani 1 1 d . . . H5 H 0.6934 0.5753 1.0541 0.030 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 O7 0.0174(18) 0.046(2) 0.041(2) -0.015(2) 0.0082(17) -0.0067(19) O2 0.0166(19) 0.042(2) 0.048(3) -0.0031(19) 0.0041(19) -0.0064(18) O1 0.024(2) 0.047(2) 0.027(2) 0.0043(19) -0.0005(18) 0.0040(19) C1 0.018(3) 0.034(3) 0.020(3) -0.004(2) 0.003(2) 0.002(2) O3 0.017(2) 0.054(2) 0.020(2) 0.0093(18) 0.0003(17) -0.0021(18) O4 0.0167(19) 0.052(2) 0.024(2) -0.0033(18) 0.0089(17) 0.0096(18) C2 0.019(3) 0.020(3) 0.021(3) -0.006(2) 0.005(2) -0.001(2) C16 0.016(3) 0.030(3) 0.018(3) 0.001(2) 0.007(2) 0.004(2) Dy1 0.01220(15) 0.03174(16) 0.02344(15) -0.00832(11) 0.00439(11) 0.00009(11) O6 0.0147(18) 0.0271(19) 0.029(2) -0.0087(16) 0.0013(16) 0.0012(15) C12 0.017(3) 0.026(3) 0.019(3) -0.008(2) 0.004(2) -0.003(2) C15 0.009(2) 0.028(3) 0.023(3) 0.005(2) 0.003(2) 0.001(2) C6 0.018(3) 0.024(3) 0.024(3) -0.004(2) 0.004(2) 0.006(2) O10 0.067(3) 0.037(2) 0.044(3) -0.002(2) 0.020(2) -0.016(2) O5 0.0157(18) 0.046(2) 0.024(2) -0.0111(17) 0.0000(16) 0.0121(17) O8 0.0172(19) 0.044(2) 0.044(2) -0.0123(19) 0.0175(19) -0.0012(17) C3 0.019(3) 0.019(3) 0.019(3) 0.000(2) 0.006(2) 0.002(2) C4 0.021(3) 0.043(3) 0.020(3) 0.002(2) 0.013(2) 0.009(2) C9 0.016(3) 0.029(3) 0.017(3) -0.003(2) 0.004(2) -0.001(2) C8 0.027(3) 0.032(3) 0.019(3) 0.002(2) 0.014(2) 0.004(2) C18 0.015(3) 0.026(3) 0.022(3) 0.004(2) 0.008(2) 0.002(2) C13 0.024(3) 0.023(3) 0.029(3) 0.001(2) 0.004(2) -0.002(2) C17 0.021(3) 0.027(3) 0.023(3) -0.007(2) 0.007(2) -0.001(2) C20 0.017(3) 0.019(3) 0.019(3) 0.003(2) 0.004(2) -0.003(2) C7 0.022(3) 0.038(3) 0.027(3) 0.003(3) 0.015(3) 0.009(2) C11 0.023(3) 0.029(3) 0.029(3) 0.003(2) 0.007(3) -0.006(2) C19 0.017(3) 0.022(3) 0.021(3) 0.000(2) 0.007(2) 0.004(2) C14 0.019(3) 0.029(3) 0.032(3) 0.002(2) 0.003(2) -0.008(2) C10 0.026(3) 0.027(3) 0.022(3) 0.006(2) 0.005(2) -0.002(2) C21 0.015(3) 0.032(3) 0.029(3) -0.001(3) 0.006(2) -0.004(2) C5 0.025(3) 0.038(3) 0.013(3) 0.002(2) 0.008(2) 0.006(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 O7 C21 1.259(6) . ? O7 Dy1 2.342(3) 5_767 ? O2 C1 1.258(6) . ? O2 Dy1 2.294(4) 4_646 ? O1 C1 1.270(6) . ? O1 Dy1 2.359(4) 8_455 ? C1 C9 1.497(7) . ? O3 C2 1.258(6) . ? O3 Dy1 2.296(3) 4_656 ? O4 C2 1.233(6) . ? O4 Dy1 2.248(3) 3_455 ? C2 C3 1.491(7) . ? C16 O5 1.372(6) . ? C16 C17 1.375(6) . ? C16 C15 1.384(7) . ? Dy1 O4 2.248(3) 3_545 ? Dy1 O8 2.294(4) . ? Dy1 O2 2.294(4) 4_656 ? Dy1 O3 2.296(3) 4_646 ? Dy1 O7 2.342(4) 5_767 ? Dy1 O1 2.359(4) 8_556 ? Dy1 O10 2.479(4) . ? O6 C12 1.392(6) . ? O6 C20 1.394(6) . ? C12 C13 1.369(7) . ? C12 C11 1.377(7) . ? C15 C20 1.374(7) . ? C6 C5 1.368(7) . ? C6 C7 1.378(7) . ? C6 O5 1.390(5) . ? O8 C21 1.254(6) . ? C3 C8 1.376(7) . ? C3 C4 1.396(7) . ? C4 C5 1.383(7) . ? C9 C14 1.380(7) . ? C9 C10 1.385(7) . ? C8 C7 1.376(7) . ? C18 C17 1.381(7) . ? C18 C19 1.394(7) . ? C18 C21 1.504(7) . ? C13 C14 1.377(7) . ? C20 C19 1.370(7) . ? C11 C10 1.374(7) . ? 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 C21 O7 Dy1 142.7(3) . 5_767 ? C1 O2 Dy1 165.5(4) . 4_646 ? C1 O1 Dy1 109.2(3) . 8_455 ? O2 C1 O1 122.6(5) . . ? O2 C1 C9 119.0(5) . . ? O1 C1 C9 118.4(5) . . ? C2 O3 Dy1 146.0(3) . 4_656 ? C2 O4 Dy1 161.3(4) . 3_455 ? O4 C2 O3 124.0(5) . . ? O4 C2 C3 118.3(4) . . ? O3 C2 C3 117.6(5) . . ? O5 C16 C17 117.9(4) . . ? O5 C16 C15 121.2(4) . . ? C17 C16 C15 120.9(5) . . ? O4 Dy1 O8 151.86(14) 3_545 . ? O4 Dy1 O2 129.25(14) 3_545 4_656 ? O8 Dy1 O2 75.05(14) . 4_656 ? O4 Dy1 O3 80.83(13) 3_545 4_646 ? O8 Dy1 O3 89.43(13) . 4_646 ? O2 Dy1 O3 83.77(13) 4_656 4_646 ? O4 Dy1 O7 75.96(13) 3_545 5_767 ? O8 Dy1 O7 129.35(13) . 5_767 ? O2 Dy1 O7 75.92(12) 4_656 5_767 ? O3 Dy1 O7 127.23(14) 4_646 5_767 ? O4 Dy1 O1 89.67(13) 3_545 8_556 ? O8 Dy1 O1 84.65(13) . 8_556 ? O2 Dy1 O1 124.63(14) 4_656 8_556 ? O3 Dy1 O1 147.78(14) 4_646 8_556 ? O7 Dy1 O1 78.94(13) 5_767 8_556 ? O4 Dy1 O10 75.78(15) 3_545 . ? O8 Dy1 O10 76.20(14) . . ? O2 Dy1 O10 144.05(14) 4_656 . ? O3 Dy1 O10 74.79(14) 4_646 . ? O7 Dy1 O10 139.90(14) 5_767 . ? O1 Dy1 O10 73.04(14) 8_556 . ? C12 O6 C20 117.5(4) . . ? C13 C12 C11 120.8(5) . . ? C13 C12 O6 117.2(4) . . ? C11 C12 O6 121.9(4) . . ? C20 C15 C16 119.0(4) . . ? C5 C6 C7 120.9(5) . . ? C5 C6 O5 116.1(4) . . ? C7 C6 O5 122.8(5) . . ? C16 O5 C6 118.5(4) . . ? C21 O8 Dy1 132.8(4) . . ? C8 C3 C4 118.6(5) . . ? C8 C3 C2 121.9(5) . . ? C4 C3 C2 119.5(5) . . ? C5 C4 C3 120.6(5) . . ? C14 C9 C10 119.4(5) . . ? C14 C9 C1 120.0(4) . . ? C10 C9 C1 120.4(5) . . ? C3 C8 C7 121.1(5) . . ? C17 C18 C19 120.5(4) . . ? C17 C18 C21 119.8(5) . . ? C19 C18 C21 119.5(4) . . ? C12 C13 C14 119.0(5) . . ? C16 C17 C18 119.3(5) . . ? C19 C20 C15 121.4(5) . . ? C19 C20 O6 117.2(4) . . ? C15 C20 O6 121.4(4) . . ? C8 C7 C6 119.5(5) . . ? C10 C11 C12 120.1(5) . . ? C20 C19 C18 118.9(5) . . ? C13 C14 C9 120.9(5) . . ? C11 C10 C9 119.7(5) . . ? O8 C21 O7 125.6(5) . . ? O8 C21 C18 117.2(5) . . ? O7 C21 C18 117.1(5) . . ? C6 C5 C4 119.3(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.948 _refine_diff_density_min -1.436 _refine_diff_density_rms 0.124 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 1 0.000 0.192 0.250 137.8 2.1 2 0.500 0.307 0.750 137.6 2.2 3 0.500 0.692 0.250 137.8 2.1 4 0.000 0.807 0.750 137.6 2.2 _platon_squeeze_details ; ? ; _database_code_depnum_ccdc_archive 'CCDC 927510' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelxs _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H11 Eu O9' _chemical_formula_weight 559.26 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' Eu Eu -0.1578 3.6682 '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 ? _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 29.797(3) _cell_length_b 9.0479(8) _cell_length_c 16.3496(14) _cell_angle_alpha 90.00 _cell_angle_beta 113.101(2) _cell_angle_gamma 90.00 _cell_volume 4054.4(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5896 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 25.01 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.832 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2176 _exptl_absorpt_coefficient_mu 3.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6013 _exptl_absorpt_correction_T_max 0.7040 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku 002 Saturn 944 area detector' _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 12553 _diffrn_reflns_av_R_equivalents 0.0625 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3571 _reflns_number_gt 3097 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert(Rigaku, 2009)' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Rigaku SHELXTL(Sheldrick, 1990)' _computing_publication_material 'Rigaku SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0717P)^2^+69.7278P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3571 _refine_ls_number_parameters 280 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0626 _refine_ls_wR_factor_ref 0.1675 _refine_ls_wR_factor_gt 0.1577 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.132 _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 C1 C 0.0798(3) 0.8823(12) -0.0071(7) 0.037(2) Uani 1 1 d U . . C2 C 0.1338(3) 0.8619(10) 0.0199(6) 0.0288(18) Uani 1 1 d U . . C3 C 0.1601(3) 0.9584(10) -0.0098(6) 0.0301(19) Uani 1 1 d U . . H3 H 0.1439 1.0323 -0.0502 0.036 Uiso 1 1 calc R . . C4 C 0.2101(3) 0.9459(10) 0.0201(6) 0.0274(18) Uani 1 1 d U . . C5 C 0.2348(3) 0.8366(9) 0.0790(6) 0.0246(17) Uani 1 1 d U . . H5 H 0.2683 0.8255 0.0972 0.030 Uiso 1 1 calc R . . C6 C 0.2083(3) 0.7438(9) 0.1104(6) 0.0254(17) Uani 1 1 d U . . C7 C 0.1578(3) 0.7522(10) 0.0811(5) 0.0236(17) Uani 1 1 d U . . H7 H 0.1406 0.6866 0.1018 0.028 Uiso 1 1 calc R . . C8 C 0.2809(3) 1.0854(10) 0.0432(6) 0.0262(18) Uani 1 1 d U . . C9 C 0.3143(3) 1.0987(11) 0.0049(6) 0.033(2) Uani 1 1 d U . . H9 H 0.3054 1.0750 -0.0548 0.040 Uiso 1 1 calc R . . C10 C 0.3617(3) 1.1476(11) 0.0549(6) 0.033(2) Uani 1 1 d U . . H10 H 0.3842 1.1563 0.0288 0.039 Uiso 1 1 calc R . . C11 C 0.3746(3) 1.1824(9) 0.1425(6) 0.0256(18) Uani 1 1 d U . . C12 C 0.3405(4) 1.1689(10) 0.1809(6) 0.0301(19) Uani 1 1 d U . . H12 H 0.3494 1.1928 0.2406 0.036 Uiso 1 1 calc R . . C13 C 0.2937(3) 1.1204(11) 0.1315(6) 0.031(2) Uani 1 1 d U . . H13 H 0.2711 1.1116 0.1575 0.037 Uiso 1 1 calc R . . C14 C 0.2815(3) 0.6494(10) 0.2242(6) 0.0260(18) Uani 1 1 d U . . C15 C 0.2989(3) 0.7732(11) 0.2743(6) 0.031(2) Uani 1 1 d U . . H15 H 0.2782 0.8516 0.2715 0.037 Uiso 1 1 calc R . . C16 C 0.3475(4) 0.7803(11) 0.3288(6) 0.034(2) Uani 1 1 d U . . H16 H 0.3599 0.8649 0.3623 0.040 Uiso 1 1 calc R . . C17 C 0.3779(3) 0.6640(11) 0.3342(6) 0.0296(19) Uani 1 1 d U . . C18 C 0.3592(3) 0.5415(11) 0.2816(6) 0.033(2) Uani 1 1 d U . . H18 H 0.3798 0.4629 0.2840 0.040 Uiso 1 1 calc R . . C19 C 0.3105(3) 0.5330(10) 0.2255(6) 0.033(2) Uani 1 1 d U . . H19 H 0.2981 0.4504 0.1899 0.039 Uiso 1 1 calc R . . C20 C 0.4259(3) 1.2375(10) 0.1964(6) 0.0284(18) Uani 1 1 d U . . C21 C 0.4289(4) 0.6652(12) 0.3999(7) 0.040(2) Uani 1 1 d U . . Eu1 Eu 0.502523(16) 0.66667(6) 0.59075(3) 0.0363(2) Uani 1 1 d U . . O1 O 0.0602(2) 0.9870(9) -0.0602(5) 0.0474(19) Uani 1 1 d U . . O2 O 0.0593(3) 0.7950(9) 0.0230(5) 0.0486(19) Uani 1 1 d U . . O3 O 0.2344(2) 1.0440(7) -0.0114(4) 0.0353(16) Uani 1 1 d U . . O4 O 0.2313(2) 0.6328(7) 0.1720(4) 0.0306(14) Uani 1 1 d U . . O5 O 0.4541(2) 1.2398(9) 0.1586(4) 0.0397(17) Uani 1 1 d U . . O6 O 0.4350(2) 1.2807(9) 0.2740(4) 0.0387(16) Uani 1 1 d U . . O7 O 0.4434(2) 0.7687(10) 0.4559(5) 0.0476(19) Uani 1 1 d U . . O8 O 0.4572(2) 0.5586(9) 0.4022(5) 0.0493(18) Uani 1 1 d U . . O9 O 0.5154(3) 0.9440(9) 0.5938(6) 0.064(2) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.017(4) 0.055(6) 0.036(6) 0.007(4) 0.008(4) 0.003(4) C2 0.022(4) 0.042(5) 0.019(5) -0.003(3) 0.003(4) 0.000(3) C3 0.020(4) 0.039(5) 0.025(5) 0.003(4) 0.002(4) 0.001(4) C4 0.024(4) 0.033(5) 0.023(5) 0.003(3) 0.006(4) -0.004(3) C5 0.010(4) 0.036(5) 0.021(5) 0.001(3) -0.001(3) 0.002(3) C6 0.026(4) 0.025(4) 0.020(4) -0.002(3) 0.003(3) 0.002(3) C7 0.015(4) 0.039(5) 0.015(4) -0.003(3) 0.004(3) -0.004(3) C8 0.019(4) 0.036(5) 0.021(4) 0.006(4) 0.004(3) -0.007(4) C9 0.026(4) 0.050(6) 0.019(4) -0.004(4) 0.004(4) -0.006(4) C10 0.016(4) 0.057(6) 0.024(4) -0.003(4) 0.006(4) -0.006(4) C11 0.027(4) 0.028(5) 0.019(4) 0.006(3) 0.007(3) -0.003(3) C12 0.035(5) 0.038(5) 0.016(4) -0.001(4) 0.009(4) -0.003(4) C13 0.029(4) 0.042(5) 0.026(4) -0.004(4) 0.014(4) -0.010(4) C14 0.021(4) 0.037(5) 0.015(4) 0.007(3) 0.002(3) -0.003(3) C15 0.023(4) 0.036(5) 0.027(5) -0.004(4) 0.003(4) 0.005(4) C16 0.033(5) 0.040(5) 0.020(5) -0.010(4) 0.002(4) -0.002(4) C17 0.012(4) 0.052(5) 0.019(5) 0.001(4) 0.000(3) -0.002(3) C18 0.027(4) 0.038(5) 0.029(5) 0.000(4) 0.004(4) 0.010(4) C19 0.024(4) 0.036(5) 0.030(5) -0.002(4) 0.002(4) -0.001(4) C20 0.027(4) 0.034(5) 0.021(4) 0.006(4) 0.007(4) 0.003(4) C21 0.026(5) 0.060(6) 0.030(5) 0.002(4) 0.007(4) 0.001(4) Eu1 0.0140(3) 0.0571(4) 0.0314(3) -0.0180(2) 0.0019(2) -0.0021(2) O1 0.023(3) 0.073(5) 0.044(5) 0.020(4) 0.010(3) 0.014(3) O2 0.029(4) 0.066(5) 0.053(5) 0.018(4) 0.018(4) 0.002(3) O3 0.022(3) 0.052(4) 0.021(3) 0.011(3) -0.003(3) -0.012(3) O4 0.016(3) 0.035(3) 0.028(4) 0.009(3) -0.005(3) -0.004(2) O5 0.022(3) 0.069(5) 0.024(4) 0.005(3) 0.005(3) -0.011(3) O6 0.012(3) 0.070(5) 0.022(3) -0.008(3) -0.006(3) 0.004(3) O7 0.018(3) 0.084(5) 0.029(4) -0.013(4) -0.003(3) -0.007(3) O8 0.016(3) 0.063(5) 0.053(5) 0.003(3) -0.004(3) 0.003(3) O9 0.076(6) 0.058(5) 0.048(5) 0.007(4) 0.015(5) -0.015(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.215(12) . ? C1 O1 1.262(12) . ? C1 C2 1.506(13) . ? C2 C3 1.381(13) . ? C2 C7 1.391(13) . ? C3 C4 1.379(12) . ? C4 O3 1.367(11) . ? C4 C5 1.375(12) . ? C5 C6 1.381(13) . ? C6 C7 1.392(12) . ? C6 O4 1.396(10) . ? C8 O3 1.373(10) . ? C8 C9 1.374(13) . ? C8 C13 1.379(13) . ? C9 C10 1.395(13) . ? C10 C11 1.366(13) . ? C11 C12 1.392(13) . ? C11 C20 1.520(13) . ? C12 C13 1.382(13) . ? C14 C19 1.358(13) . ? C14 C15 1.365(13) . ? C14 O4 1.410(10) . ? C15 C16 1.371(13) . ? C16 C17 1.368(14) . ? C17 C18 1.379(13) . ? C17 C21 1.479(13) . ? C18 C19 1.380(13) . ? C20 O5 1.223(11) . ? C20 O6 1.251(11) . ? C21 O7 1.262(13) . ? C21 O8 1.272(13) . ? Eu1 O5 2.298(6) 6_576 ? Eu1 O6 2.313(6) 5_676 ? Eu1 O8 2.345(8) 5_666 ? Eu1 O1 2.377(7) 4_545 ? Eu1 O2 2.382(8) 8_566 ? Eu1 O9 2.536(8) . ? Eu1 O8 3.003(8) . ? Eu1 Eu1 4.1923(10) 5_666 ? O1 Eu1 2.377(7) 4 ? O2 Eu1 2.382(8) 8_465 ? O5 Eu1 2.298(6) 6_575 ? O6 Eu1 2.313(6) 5_676 ? O8 Eu1 2.345(8) 5_666 ? 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 O2 C1 O1 126.6(9) . . ? O2 C1 C2 116.8(9) . . ? O1 C1 C2 116.5(9) . . ? C3 C2 C7 120.2(8) . . ? C3 C2 C1 120.5(8) . . ? C7 C2 C1 119.1(8) . . ? C4 C3 C2 120.3(9) . . ? O3 C4 C5 120.9(8) . . ? O3 C4 C3 118.1(8) . . ? C5 C4 C3 121.0(8) . . ? C4 C5 C6 118.1(8) . . ? C5 C6 C7 122.5(8) . . ? C5 C6 O4 121.0(8) . . ? C7 C6 O4 116.4(8) . . ? C2 C7 C6 117.8(8) . . ? O3 C8 C9 117.1(8) . . ? O3 C8 C13 122.4(8) . . ? C9 C8 C13 120.4(8) . . ? C8 C9 C10 120.6(9) . . ? C11 C10 C9 119.4(9) . . ? C10 C11 C12 119.9(8) . . ? C10 C11 C20 119.3(8) . . ? C12 C11 C20 120.9(8) . . ? C13 C12 C11 120.8(9) . . ? C8 C13 C12 119.1(8) . . ? C19 C14 C15 122.5(8) . . ? C19 C14 O4 116.5(8) . . ? C15 C14 O4 120.9(8) . . ? C14 C15 C16 119.0(9) . . ? C17 C16 C15 120.6(9) . . ? C16 C17 C18 118.9(8) . . ? C16 C17 C21 120.5(9) . . ? C18 C17 C21 120.5(9) . . ? C17 C18 C19 121.4(9) . . ? C14 C19 C18 117.7(9) . . ? O5 C20 O6 126.1(9) . . ? O5 C20 C11 116.6(8) . . ? O6 C20 C11 117.3(8) . . ? O7 C21 O8 120.5(9) . . ? O7 C21 C17 119.6(9) . . ? O8 C21 C17 119.8(9) . . ? O5 Eu1 O6 83.4(2) 6_576 5_676 ? O5 Eu1 O8 134.6(3) 6_576 5_666 ? O6 Eu1 O8 85.8(3) 5_676 5_666 ? O5 Eu1 O1 76.3(3) 6_576 4_545 ? O6 Eu1 O1 127.8(3) 5_676 4_545 ? O8 Eu1 O1 76.1(3) 5_666 4_545 ? O5 Eu1 O2 149.9(3) 6_576 8_566 ? O6 Eu1 O2 87.9(3) 5_676 8_566 ? O8 Eu1 O2 73.0(3) 5_666 8_566 ? O1 Eu1 O2 130.1(3) 4_545 8_566 ? O5 Eu1 O9 75.2(3) 6_576 . ? O6 Eu1 O9 73.7(3) 5_676 . ? O8 Eu1 O9 142.1(3) 5_666 . ? O1 Eu1 O9 141.3(3) 4_545 . ? O2 Eu1 O9 74.7(3) 8_566 . ? O5 Eu1 O8 120.1(2) 6_576 . ? O6 Eu1 O8 156.5(2) 5_676 . ? O8 Eu1 O8 77.5(2) 5_666 . ? O1 Eu1 O8 64.0(2) 4_545 . ? O2 Eu1 O8 71.7(2) 8_566 . ? O9 Eu1 O8 110.2(2) . . ? O5 Eu1 Eu1 138.72(19) 6_576 5_666 ? O6 Eu1 Eu1 128.06(17) 5_676 5_666 ? O8 Eu1 Eu1 44.37(19) 5_666 5_666 ? O1 Eu1 Eu1 63.40(17) 4_545 5_666 ? O2 Eu1 Eu1 67.08(18) 8_566 5_666 ? O9 Eu1 Eu1 133.6(2) . 5_666 ? O8 Eu1 Eu1 33.09(14) . 5_666 ? C1 O1 Eu1 140.5(7) . 4 ? C1 O2 Eu1 130.9(7) . 8_465 ? C4 O3 C8 118.8(7) . . ? C6 O4 C14 117.6(7) . . ? C20 O5 Eu1 159.3(7) . 6_575 ? C20 O6 Eu1 143.7(6) . 5_676 ? C21 O8 Eu1 168.8(7) . 5_666 ? C21 O8 Eu1 79.0(6) . . ? Eu1 O8 Eu1 102.5(2) 5_666 . ? 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 O2 C1 C2 C3 -178.6(10) . . . . ? O1 C1 C2 C3 2.7(14) . . . . ? O2 C1 C2 C7 -3.9(14) . . . . ? O1 C1 C2 C7 177.4(9) . . . . ? C7 C2 C3 C4 0.7(14) . . . . ? C1 C2 C3 C4 175.3(9) . . . . ? C2 C3 C4 O3 179.9(8) . . . . ? C2 C3 C4 C5 0.8(14) . . . . ? O3 C4 C5 C6 178.1(8) . . . . ? C3 C4 C5 C6 -2.8(14) . . . . ? C4 C5 C6 C7 3.4(13) . . . . ? C4 C5 C6 O4 -178.5(8) . . . . ? C3 C2 C7 C6 -0.1(13) . . . . ? C1 C2 C7 C6 -174.8(8) . . . . ? C5 C6 C7 C2 -2.0(13) . . . . ? O4 C6 C7 C2 179.8(8) . . . . ? O3 C8 C9 C10 176.7(9) . . . . ? C13 C8 C9 C10 0.2(15) . . . . ? C8 C9 C10 C11 -0.1(15) . . . . ? C9 C10 C11 C12 0.0(14) . . . . ? C9 C10 C11 C20 -179.2(9) . . . . ? C10 C11 C12 C13 0.0(14) . . . . ? C20 C11 C12 C13 179.2(8) . . . . ? O3 C8 C13 C12 -176.5(8) . . . . ? C9 C8 C13 C12 -0.1(14) . . . . ? C11 C12 C13 C8 0.0(14) . . . . ? C19 C14 C15 C16 -0.6(14) . . . . ? O4 C14 C15 C16 175.5(8) . . . . ? C14 C15 C16 C17 -1.2(15) . . . . ? C15 C16 C17 C18 2.2(15) . . . . ? C15 C16 C17 C21 -173.4(9) . . . . ? C16 C17 C18 C19 -1.3(15) . . . . ? C21 C17 C18 C19 174.2(9) . . . . ? C15 C14 C19 C18 1.4(14) . . . . ? O4 C14 C19 C18 -174.9(8) . . . . ? C17 C18 C19 C14 -0.4(15) . . . . ? C10 C11 C20 O5 -4.0(13) . . . . ? C12 C11 C20 O5 176.8(9) . . . . ? C10 C11 C20 O6 173.8(9) . . . . ? C12 C11 C20 O6 -5.4(13) . . . . ? C16 C17 C21 O7 5.5(15) . . . . ? C18 C17 C21 O7 -170.0(10) . . . . ? C16 C17 C21 O8 -177.6(10) . . . . ? C18 C17 C21 O8 6.9(15) . . . . ? O2 C1 O1 Eu1 37.0(19) . . . 4 ? C2 C1 O1 Eu1 -144.5(8) . . . 4 ? O1 C1 O2 Eu1 -48.5(17) . . . 8_465 ? C2 C1 O2 Eu1 132.9(8) . . . 8_465 ? C5 C4 O3 C8 -32.8(13) . . . . ? C3 C4 O3 C8 148.0(9) . . . . ? C9 C8 O3 C4 139.7(9) . . . . ? C13 C8 O3 C4 -43.8(13) . . . . ? C5 C6 O4 C14 22.1(12) . . . . ? C7 C6 O4 C14 -159.7(8) . . . . ? C19 C14 O4 C6 -128.3(9) . . . . ? C15 C14 O4 C6 55.3(11) . . . . ? O6 C20 O5 Eu1 -69(2) . . . 6_575 ? C11 C20 O5 Eu1 109.0(17) . . . 6_575 ? O5 C20 O6 Eu1 -19.9(18) . . . 5_676 ? C11 C20 O6 Eu1 162.6(8) . . . 5_676 ? O7 C21 O8 Eu1 122(3) . . . 5_666 ? C17 C21 O8 Eu1 -55(4) . . . 5_666 ? O7 C21 O8 Eu1 23.1(9) . . . . ? C17 C21 O8 Eu1 -153.7(9) . . . . ? O5 Eu1 O8 C21 34.0(7) 6_576 . . . ? O6 Eu1 O8 C21 -145.7(7) 5_676 . . . ? O8 Eu1 O8 C21 168.6(7) 5_666 . . . ? O1 Eu1 O8 C21 88.1(6) 4_545 . . . ? O2 Eu1 O8 C21 -115.4(6) 8_566 . . . ? O9 Eu1 O8 C21 -50.2(7) . . . . ? Eu1 Eu1 O8 C21 168.6(7) 5_666 . . . ? O5 Eu1 O8 Eu1 -134.6(3) 6_576 . . 5_666 ? O6 Eu1 O8 Eu1 45.6(7) 5_676 . . 5_666 ? O8 Eu1 O8 Eu1 0.0 5_666 . . 5_666 ? O1 Eu1 O8 Eu1 -80.5(3) 4_545 . . 5_666 ? O2 Eu1 O8 Eu1 76.0(3) 8_566 . . 5_666 ? O9 Eu1 O8 Eu1 141.2(3) . . . 5_666 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 3.688 _refine_diff_density_min -2.327 _refine_diff_density_rms 0.200 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 1 0.500 0.182 0.750 134.0 0.9 2 0.000 0.318 0.250 133.9 0.9 3 0.000 0.682 0.750 134.0 0.9 4 0.500 0.818 0.250 133.9 0.9 _platon_squeeze_details ; ? ; _database_code_depnum_ccdc_archive 'CCDC 927511' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelx _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H22 Gd2 O19' _chemical_formula_weight 1145.10 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' Gd Gd -0.1653 3.9035 '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 ? _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 29.889(9) _cell_length_b 9.4071(17) _cell_length_c 16.056(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.318(8) _cell_angle_gamma 90.00 _cell_volume 4176.3(19) _cell_formula_units_Z 4 _cell_measurement_temperature 386(2) _cell_measurement_reflns_used 5958 _cell_measurement_theta_min 1.47 _cell_measurement_theta_max 25.01 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.821 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2216 _exptl_absorpt_coefficient_mu 3.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6261 _exptl_absorpt_correction_T_max 0.7822 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 386(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku 002 Saturn 944 area detector' _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 11160 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3683 _reflns_number_gt 3182 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert(Rigaku, 2009)' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Rigaku SHELXTL (Sheldrick, 1990)' _computing_publication_material 'Rigaku SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1106P)^2^+104.6545P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3683 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0888 _refine_ls_R_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.2177 _refine_ls_wR_factor_gt 0.2039 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 C1 C 0.5694(4) 0.1572(15) 0.6019(9) 0.045(3) Uani 1 1 d . . . C2 C 0.5770(4) 0.7348(13) 0.8076(8) 0.035(3) Uani 1 1 d . . . C3 C 0.6272(4) 0.6847(11) 0.8612(7) 0.027(2) Uani 1 1 d . . . C4 C 0.6406(4) 0.6487(13) 0.9525(7) 0.038(3) Uani 1 1 d . . . H4 H 0.6182 0.6569 0.9794 0.045 Uiso 1 1 calc R . . C5 C 0.6865(4) 0.6014(13) 1.0025(7) 0.035(3) Uani 1 1 d . . . H5 H 0.6950 0.5778 1.0628 0.042 Uiso 1 1 calc R . . C6 C 0.7198(4) 0.5894(12) 0.9628(7) 0.029(2) Uani 1 1 d . . . C7 C 0.7088(4) 0.6252(12) 0.8725(7) 0.029(2) Uani 1 1 d . . . H7 H 0.7319 0.6175 0.8470 0.035 Uiso 1 1 calc R . . C8 C 0.6622(4) 0.6727(12) 0.8220(8) 0.031(2) Uani 1 1 d . . . H8 H 0.6540 0.6969 0.7619 0.037 Uiso 1 1 calc R . . C9 C 0.6215(4) 0.1633(12) 0.6677(7) 0.031(2) Uani 1 1 d . . . C10 C 0.6501(4) 0.2818(13) 0.6749(7) 0.031(2) Uani 1 1 d . . . H10 H 0.6361 0.3630 0.6423 0.037 Uiso 1 1 calc R . . C11 C 0.6993(4) 0.2837(12) 0.7294(7) 0.030(2) Uani 1 1 d . . . H11 H 0.7181 0.3644 0.7340 0.035 Uiso 1 1 calc R . . C12 C 0.7190(3) 0.1607(12) 0.7763(7) 0.027(2) Uani 1 1 d . . . C13 C 0.6913(3) 0.0385(12) 0.7726(7) 0.030(2) Uani 1 1 d . . . H13 H 0.7053 -0.0421 0.8058 0.035 Uiso 1 1 calc R . . C14 C 0.6421(4) 0.0408(13) 0.7181(7) 0.035(3) Uani 1 1 d . . . H14 H 0.6230 -0.0385 0.7151 0.042 Uiso 1 1 calc R . . C15 C 0.7654(3) 0.3440(11) 0.9236(6) 0.024(2) Uani 1 1 d . . . H15 H 0.7322 0.3333 0.9068 0.029 Uiso 1 1 calc R . . C16 C 0.7902(4) 0.4513(12) 0.9836(6) 0.026(2) Uani 1 1 d . . . C17 C 0.8400(4) 0.4657(12) 1.0135(7) 0.032(2) Uani 1 1 d . . . H17 H 0.8562 0.5373 1.0536 0.039 Uiso 1 1 calc R . . C18 C 0.8651(4) 0.3690(13) 0.9813(7) 0.032(3) Uani 1 1 d . . . C19 C 0.8411(3) 0.2631(12) 0.9191(7) 0.028(2) Uani 1 1 d . . . H19 H 0.8583 0.2002 0.8979 0.033 Uiso 1 1 calc R . . C20 C 0.7910(3) 0.2539(11) 0.8896(6) 0.024(2) Uani 1 1 d . . . C21 C 0.9194(4) 0.3940(16) 1.0078(9) 0.047(3) Uani 1 1 d . . . Gd1 Gd 0.996753(18) 0.34120(7) 0.90192(4) 0.0456(3) Uani 1 1 d . . . O1 O 0.5551(3) 0.2528(12) 0.5413(6) 0.056(3) Uani 1 1 d . . . O2 O 0.5429(3) 0.0570(11) 0.6075(7) 0.059(3) Uani 1 1 d . . . O3 O 0.5687(3) 0.7810(10) 0.7278(6) 0.045(2) Uani 1 1 d . . . O4 O 0.5463(3) 0.7223(9) 0.8430(5) 0.0357(18) Uani 1 1 d . . . O5 O 0.7665(2) 0.5453(9) 1.0181(5) 0.0349(19) Uani 1 1 d . . . O6 O 0.7689(2) 0.1478(8) 0.8286(5) 0.0290(17) Uani 1 1 d . . . O7 O 0.9386(3) 0.4932(11) 1.0612(7) 0.059(3) Uani 1 1 d . . . O8 O 0.9413(3) 0.3097(11) 0.9747(7) 0.055(3) Uani 1 1 d . . . O9 O 1.0000 0.4893(14) 0.7500 0.061(4) Uani 1 2 d S . . O10 O 0.9794(4) 0.0813(12) 0.9088(6) 0.064(3) 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 C1 0.019(6) 0.069(9) 0.038(7) 0.015(6) 0.000(5) -0.007(6) C2 0.012(5) 0.045(7) 0.039(7) -0.006(5) -0.001(5) -0.001(5) C3 0.016(5) 0.033(6) 0.023(5) -0.003(4) -0.003(4) -0.001(4) C4 0.021(6) 0.065(8) 0.023(6) -0.006(5) 0.004(5) 0.008(5) C5 0.026(6) 0.054(7) 0.021(5) -0.006(5) 0.003(4) 0.012(5) C6 0.019(5) 0.039(6) 0.021(5) -0.004(4) -0.001(4) 0.009(4) C7 0.017(5) 0.044(6) 0.025(5) 0.001(5) 0.006(4) 0.001(4) C8 0.023(5) 0.041(6) 0.025(6) 0.006(4) 0.006(5) -0.001(5) C9 0.014(5) 0.044(7) 0.029(6) 0.005(5) 0.002(4) 0.000(4) C10 0.013(5) 0.054(7) 0.022(5) 0.006(5) 0.004(4) 0.004(5) C11 0.019(5) 0.038(6) 0.025(5) 0.003(5) 0.002(4) -0.003(5) C12 0.010(5) 0.046(7) 0.021(5) -0.008(4) 0.002(4) 0.000(4) C13 0.014(5) 0.043(6) 0.027(5) 0.004(5) 0.003(4) 0.005(4) C14 0.017(5) 0.047(7) 0.033(6) 0.004(5) 0.000(4) -0.007(5) C15 0.012(5) 0.042(6) 0.015(5) -0.004(4) 0.001(4) 0.003(4) C16 0.020(5) 0.040(6) 0.016(5) -0.002(4) 0.006(4) 0.005(4) C17 0.021(5) 0.042(6) 0.025(5) -0.012(5) 0.000(4) -0.001(5) C18 0.016(5) 0.046(7) 0.025(6) -0.007(5) -0.003(4) 0.002(5) C19 0.014(5) 0.041(6) 0.025(5) -0.003(5) 0.004(4) 0.004(4) C20 0.016(5) 0.035(6) 0.019(5) 0.002(4) 0.005(4) -0.004(4) C21 0.015(5) 0.065(9) 0.054(8) -0.025(7) 0.005(5) -0.002(6) Gd1 0.0094(3) 0.0626(5) 0.0526(5) -0.0305(3) -0.0019(3) 0.0012(2) O1 0.019(4) 0.088(7) 0.049(5) 0.039(5) 0.001(4) 0.001(4) O2 0.016(4) 0.074(7) 0.068(6) 0.026(5) -0.004(4) -0.009(4) O3 0.019(4) 0.066(6) 0.040(5) 0.032(4) 0.001(4) 0.003(4) O4 0.019(4) 0.052(5) 0.031(4) -0.002(4) 0.003(3) 0.006(3) O5 0.018(4) 0.055(5) 0.021(4) -0.009(3) -0.005(3) 0.009(3) O6 0.010(3) 0.047(5) 0.023(4) -0.004(3) -0.002(3) -0.003(3) O7 0.016(4) 0.076(7) 0.073(7) -0.039(6) 0.004(4) -0.012(4) O8 0.018(4) 0.080(7) 0.062(6) -0.035(5) 0.011(4) -0.001(4) O9 0.028(6) 0.043(7) 0.084(10) 0.000 -0.009(7) 0.000 O10 0.053(6) 0.079(8) 0.043(5) -0.016(5) -0.002(4) -0.015(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.257(15) . ? C1 O1 1.273(15) . ? C1 C9 1.514(15) . ? C2 O4 1.255(14) . ? C2 O3 1.285(14) . ? C2 C3 1.494(14) . ? C3 C4 1.406(16) . ? C3 C8 1.416(16) . ? C4 C5 1.374(15) . ? C5 C6 1.374(15) . ? C6 C7 1.400(15) . ? C6 O5 1.401(11) . ? C7 C8 1.391(15) . ? C9 C10 1.383(16) . ? C9 C14 1.409(16) . ? C10 C11 1.396(14) . ? C11 C12 1.385(15) . ? C12 C13 1.406(15) . ? C12 O6 1.412(11) . ? C13 C14 1.395(14) . ? C15 C20 1.386(14) . ? C15 C16 1.397(14) . ? C16 O5 1.376(12) . ? C16 C17 1.386(14) . ? C17 C18 1.398(15) . ? C18 C19 1.400(15) . ? C18 C21 1.530(15) . ? C19 C20 1.392(13) . ? C20 O6 1.379(12) . ? C21 O7 1.250(15) . ? C21 O8 1.266(15) . ? Gd1 O3 2.321(7) 4_646 ? Gd1 O4 2.324(8) 3_545 ? Gd1 O2 2.327(9) 4_656 ? Gd1 O7 2.376(9) 5_767 ? Gd1 O8 2.383(10) . ? Gd1 O1 2.423(10) 8_556 ? Gd1 O9 2.842(6) . ? O1 Gd1 2.423(10) 8_455 ? O2 Gd1 2.327(9) 4_646 ? O3 Gd1 2.321(7) 4_656 ? O4 Gd1 2.324(8) 3_455 ? O7 Gd1 2.376(9) 5_767 ? O9 Gd1 2.842(6) 2_756 ? 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 O2 C1 O1 123.1(11) . . ? O2 C1 C9 119.2(11) . . ? O1 C1 C9 117.7(10) . . ? O4 C2 O3 125.8(9) . . ? O4 C2 C3 117.2(10) . . ? O3 C2 C3 117.0(10) . . ? C4 C3 C8 118.5(10) . . ? C4 C3 C2 120.2(10) . . ? C8 C3 C2 121.3(10) . . ? C5 C4 C3 120.9(11) . . ? C4 C5 C6 119.6(10) . . ? C5 C6 C7 122.2(9) . . ? C5 C6 O5 116.9(9) . . ? C7 C6 O5 120.9(9) . . ? C8 C7 C6 118.1(10) . . ? C7 C8 C3 120.8(10) . . ? C10 C9 C14 119.3(9) . . ? C10 C9 C1 121.9(10) . . ? C14 C9 C1 118.7(10) . . ? C9 C10 C11 122.2(11) . . ? C12 C11 C10 117.3(10) . . ? C11 C12 C13 122.6(9) . . ? C11 C12 O6 122.1(9) . . ? C13 C12 O6 115.3(9) . . ? C14 C13 C12 118.5(10) . . ? C13 C14 C9 120.0(10) . . ? C20 C15 C16 119.0(9) . . ? O5 C16 C17 116.6(9) . . ? O5 C16 C15 121.4(9) . . ? C17 C16 C15 121.9(9) . . ? C16 C17 C18 117.7(10) . . ? C17 C18 C19 121.7(10) . . ? C17 C18 C21 117.3(10) . . ? C19 C18 C21 120.7(10) . . ? C20 C19 C18 118.8(10) . . ? O6 C20 C15 122.4(9) . . ? O6 C20 C19 116.8(9) . . ? C15 C20 C19 120.8(9) . . ? O7 C21 O8 125.5(11) . . ? O7 C21 C18 117.8(10) . . ? O8 C21 C18 116.7(10) . . ? O3 Gd1 O4 88.1(3) 4_646 3_545 ? O3 Gd1 O2 85.4(3) 4_646 4_656 ? O4 Gd1 O2 141.4(4) 3_545 4_656 ? O3 Gd1 O7 135.4(4) 4_646 5_767 ? O4 Gd1 O7 80.4(3) 3_545 5_767 ? O2 Gd1 O7 77.9(3) 4_656 5_767 ? O3 Gd1 O8 84.5(3) 4_646 . ? O4 Gd1 O8 144.0(3) 3_545 . ? O2 Gd1 O8 73.0(4) 4_656 . ? O7 Gd1 O8 127.7(3) 5_767 . ? O3 Gd1 O1 143.7(4) 4_646 8_556 ? O4 Gd1 O1 81.6(3) 3_545 8_556 ? O2 Gd1 O1 123.3(3) 4_656 8_556 ? O7 Gd1 O1 77.1(4) 5_767 8_556 ? O8 Gd1 O1 83.8(3) . 8_556 ? O3 Gd1 O9 69.0(3) 4_646 . ? O4 Gd1 O9 69.6(3) 3_545 . ? O2 Gd1 O9 72.5(3) 4_656 . ? O7 Gd1 O9 66.6(3) 5_767 . ? O8 Gd1 O9 137.6(3) . . ? O1 Gd1 O9 136.4(2) 8_556 . ? C1 O1 Gd1 111.3(9) . 8_455 ? C1 O2 Gd1 165.8(11) . 4_646 ? C2 O3 Gd1 139.1(7) . 4_656 ? C2 O4 Gd1 145.8(8) . 3_455 ? C16 O5 C6 118.5(7) . . ? C20 O6 C12 118.2(8) . . ? C21 O7 Gd1 141.1(9) . 5_767 ? C21 O8 Gd1 134.0(10) . . ? Gd1 O9 Gd1 121.3(5) . 2_756 ? 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 O4 C2 C3 C4 -10.7(16) . . . . ? O3 C2 C3 C4 172.4(11) . . . . ? O4 C2 C3 C8 169.6(10) . . . . ? O3 C2 C3 C8 -7.3(16) . . . . ? C8 C3 C4 C5 -0.7(18) . . . . ? C2 C3 C4 C5 179.6(11) . . . . ? C3 C4 C5 C6 0.1(19) . . . . ? C4 C5 C6 C7 0.7(18) . . . . ? C4 C5 C6 O5 177.9(11) . . . . ? C5 C6 C7 C8 -0.8(17) . . . . ? O5 C6 C7 C8 -177.9(10) . . . . ? C6 C7 C8 C3 0.2(17) . . . . ? C4 C3 C8 C7 0.6(16) . . . . ? C2 C3 C8 C7 -179.7(10) . . . . ? O2 C1 C9 C10 -169.1(13) . . . . ? O1 C1 C9 C10 13.0(19) . . . . ? O2 C1 C9 C14 15.5(19) . . . . ? O1 C1 C9 C14 -162.4(13) . . . . ? C14 C9 C10 C11 1.2(17) . . . . ? C1 C9 C10 C11 -174.1(11) . . . . ? C9 C10 C11 C12 0.5(17) . . . . ? C10 C11 C12 C13 -1.8(16) . . . . ? C10 C11 C12 O6 175.7(9) . . . . ? C11 C12 C13 C14 1.3(16) . . . . ? O6 C12 C13 C14 -176.4(9) . . . . ? C12 C13 C14 C9 0.6(17) . . . . ? C10 C9 C14 C13 -1.8(17) . . . . ? C1 C9 C14 C13 173.7(11) . . . . ? C20 C15 C16 O5 178.7(9) . . . . ? C20 C15 C16 C17 -3.3(16) . . . . ? O5 C16 C17 C18 178.3(10) . . . . ? C15 C16 C17 C18 0.3(17) . . . . ? C16 C17 C18 C19 1.7(18) . . . . ? C16 C17 C18 C21 174.5(11) . . . . ? C17 C18 C19 C20 -0.6(17) . . . . ? C21 C18 C19 C20 -173.2(11) . . . . ? C16 C15 C20 O6 -178.5(9) . . . . ? C16 C15 C20 C19 4.4(15) . . . . ? C18 C19 C20 O6 -179.8(9) . . . . ? C18 C19 C20 C15 -2.5(16) . . . . ? C17 C18 C21 O7 4.7(19) . . . . ? C19 C18 C21 O7 177.6(13) . . . . ? C17 C18 C21 O8 -176.8(13) . . . . ? C19 C18 C21 O8 -4(2) . . . . ? O2 C1 O1 Gd1 -32.5(18) . . . 8_455 ? C9 C1 O1 Gd1 145.3(10) . . . 8_455 ? O1 C1 O2 Gd1 96(3) . . . 4_646 ? C9 C1 O2 Gd1 -82(4) . . . 4_646 ? O4 C2 O3 Gd1 -9(2) . . . 4_656 ? C3 C2 O3 Gd1 167.7(8) . . . 4_656 ? O3 C2 O4 Gd1 -70.4(18) . . . 3_455 ? C3 C2 O4 Gd1 113.0(12) . . . 3_455 ? C17 C16 O5 C6 146.6(10) . . . . ? C15 C16 O5 C6 -35.3(15) . . . . ? C5 C6 O5 C16 139.8(11) . . . . ? C7 C6 O5 C16 -43.0(15) . . . . ? C15 C20 O6 C12 22.3(14) . . . . ? C19 C20 O6 C12 -160.5(9) . . . . ? C11 C12 O6 C20 50.0(13) . . . . ? C13 C12 O6 C20 -132.3(10) . . . . ? O8 C21 O7 Gd1 31(3) . . . 5_767 ? C18 C21 O7 Gd1 -150.4(10) . . . 5_767 ? O7 C21 O8 Gd1 -49(2) . . . . ? C18 C21 O8 Gd1 132.3(10) . . . . ? O3 Gd1 O8 C21 -106.4(12) 4_646 . . . ? O4 Gd1 O8 C21 174.5(10) 3_545 . . . ? O2 Gd1 O8 C21 -19.6(11) 4_656 . . . ? O7 Gd1 O8 C21 39.6(13) 5_767 . . . ? O1 Gd1 O8 C21 108.0(12) 8_556 . . . ? O9 Gd1 O8 C21 -56.3(13) . . . . ? O3 Gd1 O9 Gd1 -58.9(2) 4_646 . . 2_756 ? O4 Gd1 O9 Gd1 37.1(2) 3_545 . . 2_756 ? O2 Gd1 O9 Gd1 -150.7(2) 4_656 . . 2_756 ? O7 Gd1 O9 Gd1 125.2(3) 5_767 . . 2_756 ? O8 Gd1 O9 Gd1 -113.9(4) . . . 2_756 ? O1 Gd1 O9 Gd1 89.1(4) 8_556 . . 2_756 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 3.076 _refine_diff_density_min -3.512 _refine_diff_density_rms 0.270 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 1 0.000 0.156 0.250 146.1 19.3 2 0.500 0.344 0.750 146.0 18.1 3 0.500 0.656 0.250 146.1 19.3 4 0.000 0.844 0.750 145.9 18.1 _platon_squeeze_details ; ? ; _database_code_depnum_ccdc_archive 'CCDC 927512' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelx2 #TrackingRef 'Ho.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H13 Ho O9.5' _chemical_formula_weight 588.23 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' Ho Ho -0.2175 4.6783 '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 29.66(3) _cell_length_b 9.249(8) _cell_length_c 16.298(14) _cell_angle_alpha 90.00 _cell_angle_beta 112.872(11) _cell_angle_gamma 90.00 _cell_volume 4120(6) _cell_formula_units_Z 8 _cell_measurement_temperature 386(2) _cell_measurement_reflns_used 5750 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.8 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2272 _exptl_absorpt_coefficient_mu 3.898 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.544 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 386(2) _diffrn_radiation_wavelength 0.71075 _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 13528 _diffrn_reflns_av_R_equivalents 0.0848 _diffrn_reflns_av_sigmaI/netI 0.0786 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3634 _reflns_number_gt 2625 _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^)+(0.1598P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3634 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1146 _refine_ls_R_factor_gt 0.0900 _refine_ls_wR_factor_ref 0.2742 _refine_ls_wR_factor_gt 0.2465 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 1.199 _refine_ls_shift/su_mean 0.004 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 O15 O 0.50387(19) 0.8945(5) 0.6428(4) 0.0078(12) Uani 1 1 d . . . O5 O 0.4568(3) 0.0539(16) 0.8884(8) 0.101(5) Uani 1 1 d . . . O6 O 0.4441(3) 0.2479(19) 0.9563(8) 0.109(5) Uani 1 1 d . . . O2 O 0.0593(3) 0.4936(14) 0.4427(9) 0.095(4) Uani 1 1 d . . . O1 O 0.0560(3) 0.3074(15) 0.5228(9) 0.100(5) Uani 1 1 d . . . C1 C 0.0787(5) 0.3867(17) 0.4955(11) 0.075(5) Uani 1 1 d . . . O7 O 0.4331(3) 0.7757(12) 0.7752(6) 0.064(3) Uani 1 1 d . . . Ho1 Ho 0.50290(2) 0.83762(12) 0.59505(7) 0.0867(5) Uani 1 1 d . . . O3 O 0.2295(2) 0.1408(7) 0.6717(5) 0.0359(16) Uani 1 1 d . . . C4 C 0.3387(4) 0.6697(12) 0.6799(8) 0.043(3) Uani 1 1 d . . . H4 H 0.3471 0.6923 0.7397 0.052 Uiso 1 1 calc R . . C5 C 0.3776(4) 0.1606(15) 0.8305(8) 0.058(3) Uani 1 1 d . . . C6 C 0.2333(4) 0.3385(10) 0.5769(7) 0.037(2) Uani 1 1 d . . . H6 H 0.2668 0.3256 0.5938 0.044 Uiso 1 1 calc R . . C7 C 0.2798(4) 0.1550(12) 0.7233(7) 0.036(2) Uani 1 1 d . . . O4 O 0.2334(2) 0.5426(8) 0.4860(4) 0.0380(17) Uani 1 1 d . . . C8 C 0.4245(4) 0.7413(14) 0.6968(9) 0.054(3) Uani 1 1 d . . . C9 C 0.3077(4) 0.0337(11) 0.7249(7) 0.040(2) Uani 1 1 d . . . H9 H 0.2938 -0.0476 0.6908 0.048 Uiso 1 1 calc R . . O8 O 0.4537(3) 0.7375(12) 0.6572(6) 0.068(3) Uani 1 1 d . . . C10 C 0.3744(4) 0.6850(12) 0.6424(8) 0.044(3) Uani 1 1 d . . . C11 C 0.2805(4) 0.5815(11) 0.5404(6) 0.037(2) Uani 1 1 d . . . C12 C 0.2916(4) 0.6220(11) 0.6302(7) 0.038(2) Uani 1 1 d . . . H12 H 0.2681 0.6167 0.6547 0.046 Uiso 1 1 calc R . . C13 C 0.1593(4) 0.4633(13) 0.4902(7) 0.045(3) Uani 1 1 d . . . H13 H 0.1433 0.5367 0.4505 0.054 Uiso 1 1 calc R . . C14 C 0.2072(3) 0.2481(10) 0.6102(6) 0.030(2) Uani 1 1 d . . . C15 C 0.3596(4) 0.6495(13) 0.5514(8) 0.049(3) Uani 1 1 d . . . H15 H 0.3816 0.6605 0.5239 0.059 Uiso 1 1 calc R . . C16 C 0.1332(4) 0.3703(15) 0.5208(9) 0.060(4) Uani 1 1 d . . . C17 C 0.2095(4) 0.4469(11) 0.5188(6) 0.036(2) Uani 1 1 d . . . C18 C 0.3586(4) 0.0384(14) 0.7811(8) 0.054(3) Uani 1 1 d . . . H18 H 0.3787 -0.0404 0.7842 0.064 Uiso 1 1 calc R . . C20 C 0.1571(4) 0.2594(12) 0.5819(7) 0.040(2) Uani 1 1 d . . . H20 H 0.1395 0.1958 0.6023 0.048 Uiso 1 1 calc R . . C21 C 0.3492(4) 0.2776(14) 0.8269(7) 0.046(3) Uani 1 1 d . . . H21 H 0.3630 0.3593 0.8606 0.056 Uiso 1 1 calc R . . C22 C 0.2991(4) 0.2760(12) 0.7726(7) 0.039(2) Uani 1 1 d . . . H22 H 0.2794 0.3555 0.7702 0.046 Uiso 1 1 calc R . . C23 C 0.4299(5) 0.1529(18) 0.8956(9) 0.071(5) Uani 1 1 d . . . C24 C 0.3140(4) 0.5998(13) 0.5033(7) 0.043(2) Uani 1 1 d . . . H24 H 0.3054 0.5776 0.4435 0.052 Uiso 1 1 calc R . . O11 O 0.5141(4) 0.5682(18) 0.5880(7) 0.102(4) 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 O15 0.000(3) 0.018(2) 0.003(2) 0.0014(19) -0.002(2) 0.0073(19) O5 0.018(5) 0.152(11) 0.110(9) -0.058(8) 0.000(5) 0.003(6) O6 0.010(4) 0.206(14) 0.095(8) -0.070(10) 0.004(5) -0.011(7) O2 0.021(5) 0.133(10) 0.122(9) 0.052(8) 0.019(6) 0.005(5) O1 0.014(4) 0.149(10) 0.121(9) 0.078(8) 0.008(5) 0.002(5) C1 0.016(6) 0.093(10) 0.092(11) 0.045(9) -0.004(7) 0.011(7) O7 0.023(4) 0.101(7) 0.055(6) -0.031(5) -0.001(4) 0.000(4) Ho1 0.0134(4) 0.1375(9) 0.0913(8) 0.0574(6) 0.0011(4) -0.0002(4) O3 0.008(3) 0.055(4) 0.040(4) 0.007(3) 0.004(3) 0.000(3) C4 0.021(6) 0.060(6) 0.048(6) -0.013(5) 0.012(5) -0.007(5) C5 0.013(6) 0.106(10) 0.046(7) -0.016(6) 0.004(5) -0.003(6) C6 0.018(5) 0.050(5) 0.036(5) -0.011(4) 0.004(4) -0.004(4) C7 0.011(5) 0.067(6) 0.033(5) 0.006(4) 0.009(4) -0.001(4) O4 0.014(3) 0.063(4) 0.030(3) 0.007(3) 0.000(3) -0.011(3) C8 0.014(5) 0.072(8) 0.070(9) 0.022(7) 0.009(6) 0.003(5) C9 0.014(5) 0.049(6) 0.048(6) -0.004(4) 0.002(4) 0.006(4) O8 0.021(4) 0.101(7) 0.063(6) 0.017(5) -0.004(4) -0.010(4) C10 0.018(5) 0.062(7) 0.050(7) 0.009(5) 0.010(5) -0.003(5) C11 0.020(5) 0.048(6) 0.032(5) 0.007(4) -0.001(4) -0.003(4) C12 0.019(5) 0.053(6) 0.037(5) -0.005(4) 0.005(4) -0.007(4) C13 0.017(5) 0.066(7) 0.045(6) 0.018(5) 0.003(5) 0.008(5) C14 0.019(4) 0.042(5) 0.027(5) 0.000(4) 0.007(4) -0.005(4) C15 0.025(6) 0.076(8) 0.046(6) 0.003(5) 0.013(5) -0.010(5) C16 0.011(5) 0.084(9) 0.070(8) 0.021(7) -0.002(6) -0.005(5) C17 0.020(5) 0.050(5) 0.032(5) -0.002(4) 0.003(4) -0.006(4) C18 0.012(5) 0.076(8) 0.060(7) -0.016(6) 0.000(5) 0.000(5) C20 0.017(5) 0.057(6) 0.041(6) 0.008(5) 0.005(4) 0.000(4) C21 0.024(6) 0.072(7) 0.041(6) -0.016(5) 0.011(5) -0.019(6) C22 0.017(5) 0.059(6) 0.037(5) -0.001(5) 0.007(4) 0.004(5) C23 0.023(7) 0.121(12) 0.053(8) -0.041(8) -0.002(6) -0.016(7) C24 0.028(5) 0.065(7) 0.039(6) 0.004(5) 0.015(5) 0.001(5) O11 0.059(7) 0.153(12) 0.083(8) 0.002(7) 0.017(6) 0.016(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O5 C23 1.249(19) . ? O5 Ho1 2.292(14) 2_646 ? O6 C23 1.267(18) . ? O6 Ho1 2.391(14) 6_566 ? O2 C1 1.291(16) . ? O2 Ho1 2.310(11) 7_566 ? O1 C1 1.193(18) . ? O1 Ho1 2.320(14) 3_445 ? C1 C16 1.512(17) . ? O7 C8 1.243(17) . ? O7 Ho1 2.299(8) 2_656 ? Ho1 O8 2.271(10) . ? Ho1 O5 2.292(14) 2_666 ? Ho1 O7 2.299(8) 2_656 ? Ho1 O2 2.310(11) 7_566 ? Ho1 O1 2.320(14) 3 ? Ho1 O6 2.391(14) 6_565 ? Ho1 O11 2.523(16) . ? O3 C14 1.383(11) . ? O3 C7 1.405(11) . ? C4 C12 1.385(15) . ? C4 C10 1.424(17) . ? C5 C21 1.359(18) . ? C5 C18 1.375(17) . ? C5 C23 1.504(17) . ? C6 C17 1.371(14) . ? C6 C14 1.386(15) . ? C7 C22 1.367(16) . ? C7 C9 1.387(15) . ? O4 C17 1.366(13) . ? O4 C11 1.381(11) . ? C8 O8 1.268(16) . ? C8 C10 1.496(15) . ? C9 C18 1.430(13) . ? C10 C15 1.412(17) . ? C11 C24 1.358(16) . ? C11 C12 1.420(15) . ? C13 C16 1.374(18) . ? C13 C17 1.386(14) . ? C14 C20 1.378(14) . ? C15 C24 1.353(16) . ? C16 C20 1.413(16) . ? C21 C22 1.404(14) . ? 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 C23 O5 Ho1 162.1(14) . 2_646 ? C23 O6 Ho1 114.1(13) . 6_566 ? C1 O2 Ho1 143.0(11) . 7_566 ? C1 O1 Ho1 135.1(14) . 3_445 ? O1 C1 O2 123.3(13) . . ? O1 C1 C16 122.4(11) . . ? O2 C1 C16 114.3(13) . . ? C8 O7 Ho1 140.8(8) . 2_656 ? O8 Ho1 O5 134.4(5) . 2_666 ? O8 Ho1 O7 86.1(3) . 2_656 ? O5 Ho1 O7 84.4(4) 2_666 2_656 ? O8 Ho1 O2 79.0(4) . 7_566 ? O5 Ho1 O2 76.6(4) 2_666 7_566 ? O7 Ho1 O2 134.6(5) 2_656 7_566 ? O8 Ho1 O1 149.0(5) . 3 ? O5 Ho1 O1 74.9(5) 2_666 3 ? O7 Ho1 O1 87.5(4) 2_656 3 ? O2 Ho1 O1 125.1(4) 7_566 3 ? O8 Ho1 O6 85.9(4) . 6_565 ? O5 Ho1 O6 123.7(4) 2_666 6_565 ? O7 Ho1 O6 145.7(5) 2_656 6_565 ? O2 Ho1 O6 76.0(5) 7_566 6_565 ? O1 Ho1 O6 82.5(4) 3 6_565 ? O8 Ho1 O11 74.7(4) . . ? O5 Ho1 O11 142.7(4) 2_666 . ? O7 Ho1 O11 73.7(4) 2_656 . ? O2 Ho1 O11 139.5(4) 7_566 . ? O1 Ho1 O11 74.4(5) 3 . ? O6 Ho1 O11 72.0(5) 6_565 . ? C14 O3 C7 117.7(8) . . ? C12 C4 C10 122.0(11) . . ? C21 C5 C18 121.6(11) . . ? C21 C5 C23 121.4(12) . . ? C18 C5 C23 116.7(12) . . ? C17 C6 C14 119.7(10) . . ? C22 C7 C9 122.8(10) . . ? C22 C7 O3 122.1(10) . . ? C9 C7 O3 114.9(9) . . ? C17 O4 C11 117.8(7) . . ? O7 C8 O8 128.6(11) . . ? O7 C8 C10 117.3(12) . . ? O8 C8 C10 114.0(12) . . ? C7 C9 C18 117.4(10) . . ? C8 O8 Ho1 154.3(10) . . ? C15 C10 C4 116.6(10) . . ? C15 C10 C8 122.5(11) . . ? C4 C10 C8 120.9(11) . . ? C24 C11 O4 118.7(9) . . ? C24 C11 C12 120.6(9) . . ? O4 C11 C12 120.1(10) . . ? C4 C12 C11 117.7(11) . . ? C16 C13 C17 119.5(10) . . ? C20 C14 O3 116.6(8) . . ? C20 C14 C6 121.1(9) . . ? O3 C14 C6 122.2(9) . . ? C24 C15 C10 121.4(12) . . ? C13 C16 C20 120.8(11) . . ? C13 C16 C1 122.1(11) . . ? C20 C16 C1 117.1(11) . . ? O4 C17 C6 122.5(9) . . ? O4 C17 C13 116.7(9) . . ? C6 C17 C13 120.7(10) . . ? C5 C18 C9 119.4(11) . . ? C14 C20 C16 118.1(10) . . ? C5 C21 C22 120.4(11) . . ? C7 C22 C21 118.5(10) . . ? O5 C23 O6 123.5(13) . . ? O5 C23 C5 119.4(11) . . ? O6 C23 C5 117.1(14) . . ? C15 C24 C11 121.6(11) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 3.918 _refine_diff_density_min -2.307 _refine_diff_density_rms 0.268 _database_code_depnum_ccdc_archive 'CCDC 927513' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H11 Nd O9' _chemical_formula_weight 551.54 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' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _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 29.762(6) _cell_length_b 9.1425(18) _cell_length_c 16.364(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.39(3) _cell_angle_gamma 90.00 _cell_volume 4086.7(14) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5970 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 25.01 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.793 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2152 _exptl_absorpt_coefficient_mu 2.592 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6818 _exptl_absorpt_correction_T_max 0.7462 _exptl_absorpt_process_details SADABS _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 'Rigaku 002 Saturn 944 area detector' _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 12636 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_sigmaI/netI 0.0625 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3595 _reflns_number_gt 2874 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert(Rigaku, 2009)' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Rigaku SHELXTL(Sheldrick, 1990)' _computing_publication_material 'Rigaku SHELXTL-97' _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^)+(0.0691P)^2^+10.1493P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3595 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0456 _refine_ls_wR_factor_ref 0.1310 _refine_ls_wR_factor_gt 0.1248 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Nd1 Nd 0.497310(12) -0.16375(5) 0.40641(3) 0.04000(18) Uani 1 1 d . . . O1 O 0.56044(16) 0.0202(6) 0.4366(3) 0.0501(13) Uani 1 1 d . . . O2 O 0.55836(17) 0.2086(6) 0.5215(4) 0.0482(13) Uani 1 1 d . . . O3 O 0.73303(15) -0.0434(5) 0.4865(3) 0.0370(11) Uani 1 1 d . . . O4 O 0.73119(15) 0.3653(4) 0.6711(3) 0.0324(11) Uani 1 1 d . . . O5 O 0.94134(18) 0.2295(7) 0.9567(3) 0.0552(14) Uani 1 1 d . . . O6 O 0.95626(16) 0.4394(6) 0.9059(4) 0.0577(15) Uani 1 1 d . . . O7 O 0.95246(16) -0.2343(6) 0.6579(3) 0.0430(12) Uani 1 1 d . . . O8 O 0.93238(16) -0.2734(6) 0.7729(3) 0.0434(12) Uani 1 1 d . . . O10 O 0.4846(2) -0.4449(7) 0.4075(4) 0.0710(17) Uani 1 1 d . . . C1 C 0.5797(2) 0.1230(9) 0.4893(5) 0.0398(17) Uani 1 1 d . . . C2 C 0.6344(2) 0.1404(7) 0.5192(4) 0.0297(15) Uani 1 1 d . . . C3 C 0.6583(2) 0.2467(7) 0.5801(4) 0.0284(14) Uani 1 1 d . . . H3 H 0.6410 0.3107 0.6010 0.034 Uiso 1 1 calc R . . C4 C 0.7081(2) 0.2566(6) 0.6093(4) 0.0243(13) Uani 1 1 d . . . C5 C 0.7340(2) 0.1628(6) 0.5778(4) 0.0271(14) Uani 1 1 d . . . H5 H 0.7677 0.1728 0.5958 0.032 Uiso 1 1 calc R . . C6 C 0.7092(2) 0.0551(7) 0.5195(4) 0.0266(14) Uani 1 1 d . . . C7 C 0.6597(2) 0.0428(7) 0.4889(4) 0.0315(15) Uani 1 1 d . . . H7 H 0.6432 -0.0298 0.4483 0.038 Uiso 1 1 calc R . . C8 C 0.7805(2) 0.3494(6) 0.7232(4) 0.0250(14) Uani 1 1 d . . . C9 C 0.8098(2) 0.4648(7) 0.7269(4) 0.0334(15) Uani 1 1 d . . . H9 H 0.7973 0.5467 0.6914 0.040 Uiso 1 1 calc R . . C10 C 0.8590(2) 0.4588(7) 0.7849(5) 0.0366(16) Uani 1 1 d . . . H10 H 0.8795 0.5379 0.7896 0.044 Uiso 1 1 calc R . . C11 C 0.8769(2) 0.3364(7) 0.8347(4) 0.0304(15) Uani 1 1 d . . . C12 C 0.8466(2) 0.2196(7) 0.8287(4) 0.0322(15) Uani 1 1 d . . . H12 H 0.8590 0.1365 0.8630 0.039 Uiso 1 1 calc R . . C13 C 0.7983(2) 0.2252(7) 0.7726(4) 0.0332(15) Uani 1 1 d . . . H13 H 0.7778 0.1461 0.7679 0.040 Uiso 1 1 calc R . . C14 C 0.7797(2) -0.0860(7) 0.5411(4) 0.0299(14) Uani 1 1 d . . . C15 C 0.7920(2) -0.1213(7) 0.6298(4) 0.0329(15) Uani 1 1 d . . . H15 H 0.7691 -0.1134 0.6550 0.039 Uiso 1 1 calc R . . C16 C 0.8385(2) -0.1679(6) 0.6794(4) 0.0296(14) Uani 1 1 d . . . H16 H 0.8473 -0.1909 0.7392 0.036 Uiso 1 1 calc R . . C17 C 0.8729(2) -0.1815(6) 0.6416(4) 0.0265(14) Uani 1 1 d . . . C18 C 0.8588(2) -0.1468(7) 0.5526(5) 0.0369(16) Uani 1 1 d . . . H18 H 0.8812 -0.1564 0.5263 0.044 Uiso 1 1 calc R . . C19 C 0.8127(2) -0.0989(8) 0.5030(4) 0.0345(15) Uani 1 1 d . . . H19 H 0.8038 -0.0751 0.4433 0.041 Uiso 1 1 calc R . . C20 C 0.9225(2) -0.2350(7) 0.6940(4) 0.0316(15) Uani 1 1 d . . . C21 C 0.9284(2) 0.3333(9) 0.9029(5) 0.0412(18) 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 Nd1 0.0140(2) 0.0665(3) 0.0335(3) -0.0162(2) 0.00312(18) -0.00581(17) O1 0.026(2) 0.073(4) 0.046(3) -0.014(3) 0.009(2) -0.016(3) O2 0.020(2) 0.074(3) 0.050(3) -0.010(3) 0.013(3) -0.001(2) O3 0.023(2) 0.049(3) 0.027(3) -0.010(2) -0.003(2) 0.013(2) O4 0.016(2) 0.034(2) 0.036(3) -0.009(2) -0.002(2) 0.0025(18) O5 0.027(3) 0.094(4) 0.032(3) 0.011(3) -0.002(2) 0.011(3) O6 0.015(2) 0.071(4) 0.069(4) -0.014(3) -0.002(3) -0.007(2) O7 0.021(2) 0.077(3) 0.026(3) -0.003(3) 0.004(2) 0.007(2) O8 0.026(3) 0.068(3) 0.030(3) 0.010(3) 0.004(2) 0.001(2) O10 0.069(4) 0.069(4) 0.059(4) 0.011(3) 0.009(3) -0.018(3) C1 0.022(3) 0.065(5) 0.029(4) -0.002(4) 0.006(3) -0.007(3) C2 0.017(3) 0.040(4) 0.027(4) 0.004(3) 0.004(3) -0.004(3) C3 0.019(3) 0.039(4) 0.026(4) 0.000(3) 0.007(3) 0.002(3) C4 0.020(3) 0.027(3) 0.021(3) 0.004(3) 0.003(3) -0.001(3) C5 0.014(3) 0.039(4) 0.024(4) 0.006(3) 0.004(3) 0.000(3) C6 0.024(3) 0.031(3) 0.021(3) -0.003(3) 0.004(3) 0.002(3) C7 0.023(3) 0.040(4) 0.026(4) -0.004(3) 0.003(3) 0.000(3) C8 0.016(3) 0.033(4) 0.018(3) -0.007(3) -0.002(3) 0.000(3) C9 0.030(3) 0.029(4) 0.035(4) 0.002(3) 0.006(3) 0.002(3) C10 0.022(3) 0.039(4) 0.041(4) -0.007(3) 0.004(3) -0.010(3) C11 0.018(3) 0.044(4) 0.023(4) -0.002(3) 0.002(3) 0.003(3) C12 0.028(4) 0.040(4) 0.021(4) 0.008(3) 0.001(3) 0.000(3) C13 0.027(3) 0.037(4) 0.029(4) 0.005(3) 0.003(3) -0.005(3) C14 0.025(3) 0.030(3) 0.028(4) -0.001(3) 0.002(3) 0.007(3) C15 0.030(4) 0.038(4) 0.032(4) 0.000(3) 0.014(3) 0.005(3) C16 0.029(4) 0.036(4) 0.022(3) -0.002(3) 0.009(3) 0.004(3) C17 0.025(3) 0.027(3) 0.024(4) -0.001(3) 0.005(3) -0.001(3) C18 0.030(4) 0.053(4) 0.030(4) 0.001(3) 0.014(3) 0.005(3) C19 0.028(3) 0.051(4) 0.019(3) 0.005(3) 0.004(3) 0.008(3) C20 0.020(3) 0.041(4) 0.026(4) -0.003(3) 0.001(3) 0.000(3) C21 0.019(4) 0.069(5) 0.028(4) -0.007(4) 0.001(3) 0.006(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 Nd1 O7 2.337(4) 7_646 ? Nd1 O8 2.342(5) 8_445 ? Nd1 O6 2.386(5) 8_455 ? Nd1 O2 2.419(5) 5_656 ? Nd1 O1 2.422(5) . ? Nd1 O5 2.461(6) 4_646 ? Nd1 O10 2.599(6) . ? Nd1 C21 3.025(7) 4_646 ? O1 C1 1.249(8) . ? O2 C1 1.249(8) . ? O2 Nd1 2.419(5) 5_656 ? O3 C14 1.375(7) . ? O3 C6 1.384(7) . ? O4 C8 1.381(7) . ? O4 C4 1.389(7) . ? O5 C21 1.247(9) . ? O5 Nd1 2.461(6) 4_656 ? O6 C21 1.265(9) . ? O6 Nd1 2.386(5) 8_556 ? O7 C20 1.248(7) . ? O7 Nd1 2.337(4) 7_646 ? O8 C20 1.257(8) . ? O8 Nd1 2.342(5) 8_546 ? C1 C2 1.512(9) . ? C2 C3 1.371(9) . ? C2 C7 1.380(8) . ? C3 C4 1.369(8) . ? C3 H3 0.9300 . ? C4 C5 1.384(8) . ? C5 C6 1.366(8) . ? C5 H5 0.9300 . ? C6 C7 1.359(8) . ? C7 H7 0.9300 . ? C8 C9 1.356(8) . ? C8 C13 1.372(9) . ? C9 C10 1.394(9) . ? C9 H9 0.9300 . ? C10 C11 1.362(9) . ? C10 H10 0.9300 . ? C11 C12 1.376(9) . ? C11 C21 1.496(9) . ? C12 C13 1.365(9) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C19 1.363(8) . ? C14 C15 1.387(9) . ? C15 C16 1.364(9) . ? C15 H15 0.9300 . ? C16 C17 1.397(8) . ? C16 H16 0.9300 . ? C17 C18 1.383(9) . ? C17 C20 1.466(9) . ? C18 C19 1.360(9) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C21 Nd1 3.025(7) 4_656 ? 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 O7 Nd1 O8 85.44(16) 7_646 8_445 ? O7 Nd1 O6 139.43(19) 7_646 8_455 ? O8 Nd1 O6 88.63(18) 8_445 8_455 ? O7 Nd1 O2 146.74(19) 7_646 5_656 ? O8 Nd1 O2 86.66(17) 8_445 5_656 ? O6 Nd1 O2 72.46(18) 8_455 5_656 ? O7 Nd1 O1 77.62(17) 7_646 . ? O8 Nd1 O1 130.29(18) 8_445 . ? O6 Nd1 O1 76.01(17) 8_455 . ? O2 Nd1 O1 130.11(17) 5_656 . ? O7 Nd1 O5 82.86(17) 7_646 4_646 ? O8 Nd1 O5 142.3(2) 8_445 4_646 ? O6 Nd1 O5 122.6(2) 8_455 4_646 ? O2 Nd1 O5 83.88(17) 5_656 4_646 ? O1 Nd1 O5 81.66(19) . 4_646 ? O7 Nd1 O10 74.31(19) 7_646 . ? O8 Nd1 O10 72.23(18) 8_445 . ? O6 Nd1 O10 140.75(18) 8_455 . ? O2 Nd1 O10 72.50(19) 5_656 . ? O1 Nd1 O10 142.08(19) . . ? O5 Nd1 O10 70.08(19) 4_646 . ? O7 Nd1 C21 97.15(18) 7_646 4_646 ? O8 Nd1 C21 162.67(19) 8_445 4_646 ? O6 Nd1 C21 100.1(2) 8_455 4_646 ? O2 Nd1 C21 81.81(17) 5_656 4_646 ? O1 Nd1 C21 66.78(18) . 4_646 ? O5 Nd1 C21 23.52(19) 4_646 4_646 ? O10 Nd1 C21 91.9(2) . 4_646 ? C1 O1 Nd1 140.2(4) . . ? C1 O2 Nd1 131.4(5) . 5_656 ? C14 O3 C6 118.2(5) . . ? C8 O4 C4 118.1(4) . . ? C21 O5 Nd1 104.5(5) . 4_656 ? C21 O6 Nd1 170.6(5) . 8_556 ? C20 O7 Nd1 156.2(5) . 7_646 ? C20 O8 Nd1 142.8(4) . 8_546 ? O2 C1 O1 126.4(6) . . ? O2 C1 C2 117.4(6) . . ? O1 C1 C2 116.2(6) . . ? C3 C2 C7 121.4(6) . . ? C3 C2 C1 119.4(6) . . ? C7 C2 C1 119.1(6) . . ? C4 C3 C2 118.5(6) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 121.1(6) . . ? C3 C4 O4 117.2(5) . . ? C5 C4 O4 121.8(5) . . ? C6 C5 C4 118.6(5) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C7 C6 C5 121.7(6) . . ? C7 C6 O3 116.8(5) . . ? C5 C6 O3 121.4(5) . . ? C6 C7 C2 118.6(6) . . ? C6 C7 H7 120.7 . . ? C2 C7 H7 120.7 . . ? C9 C8 C13 121.8(6) . . ? C9 C8 O4 116.9(5) . . ? C13 C8 O4 121.2(5) . . ? C8 C9 C10 118.9(6) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 119.7(6) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.4(6) . . ? C10 C11 C21 120.2(6) . . ? C12 C11 C21 119.1(6) . . ? C13 C12 C11 120.3(6) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C8 119.0(6) . . ? C12 C13 H13 120.5 . . ? C8 C13 H13 120.5 . . ? C19 C14 O3 117.0(6) . . ? C19 C14 C15 121.3(6) . . ? O3 C14 C15 121.7(5) . . ? C16 C15 C14 118.7(6) . . ? C16 C15 H15 120.6 . . ? C14 C15 H15 120.6 . . ? C15 C16 C17 120.8(6) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C18 C17 C16 118.5(6) . . ? C18 C17 C20 120.4(6) . . ? C16 C17 C20 121.1(6) . . ? C19 C18 C17 121.0(6) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C14 119.7(6) . . ? C18 C19 H19 120.2 . . ? C14 C19 H19 120.2 . . ? O7 C20 O8 124.7(6) . . ? O7 C20 C17 117.7(6) . . ? O8 C20 C17 117.6(6) . . ? O5 C21 O6 122.8(7) . . ? O5 C21 C11 118.7(7) . . ? O6 C21 C11 118.5(7) . . ? O5 C21 Nd1 52.0(4) . 4_656 ? O6 C21 Nd1 75.7(4) . 4_656 ? C11 C21 Nd1 151.9(5) . 4_656 ? 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 O7 Nd1 O1 C1 -157.1(8) 7_646 . . . ? O8 Nd1 O1 C1 130.0(7) 8_445 . . . ? O6 Nd1 O1 C1 54.1(8) 8_455 . . . ? O2 Nd1 O1 C1 2.1(9) 5_656 . . . ? O5 Nd1 O1 C1 -72.6(8) 4_646 . . . ? O10 Nd1 O1 C1 -114.1(8) . . . . ? C21 Nd1 O1 C1 -53.6(8) 4_646 . . . ? Nd1 O2 C1 O1 48.9(11) 5_656 . . . ? Nd1 O2 C1 C2 -128.4(5) 5_656 . . . ? Nd1 O1 C1 O2 -36.0(13) . . . . ? Nd1 O1 C1 C2 141.4(5) . . . . ? O2 C1 C2 C3 0.5(10) . . . . ? O1 C1 C2 C3 -177.1(6) . . . . ? O2 C1 C2 C7 176.5(6) . . . . ? O1 C1 C2 C7 -1.2(10) . . . . ? C7 C2 C3 C4 1.3(9) . . . . ? C1 C2 C3 C4 177.2(6) . . . . ? C2 C3 C4 C5 0.7(9) . . . . ? C2 C3 C4 O4 -179.9(5) . . . . ? C8 O4 C4 C3 158.8(6) . . . . ? C8 O4 C4 C5 -21.8(8) . . . . ? C3 C4 C5 C6 -2.9(9) . . . . ? O4 C4 C5 C6 177.7(5) . . . . ? C4 C5 C6 C7 3.3(9) . . . . ? C4 C5 C6 O3 -179.1(5) . . . . ? C14 O3 C6 C7 -148.4(6) . . . . ? C14 O3 C6 C5 33.9(8) . . . . ? C5 C6 C7 C2 -1.4(10) . . . . ? O3 C6 C7 C2 -179.1(5) . . . . ? C3 C2 C7 C6 -1.0(10) . . . . ? C1 C2 C7 C6 -176.8(6) . . . . ? C4 O4 C8 C9 129.5(6) . . . . ? C4 O4 C8 C13 -53.9(8) . . . . ? C13 C8 C9 C10 -2.3(9) . . . . ? O4 C8 C9 C10 174.3(6) . . . . ? C8 C9 C10 C11 1.7(10) . . . . ? C9 C10 C11 C12 -0.6(10) . . . . ? C9 C10 C11 C21 -174.7(6) . . . . ? C10 C11 C12 C13 0.1(10) . . . . ? C21 C11 C12 C13 174.2(6) . . . . ? C11 C12 C13 C8 -0.7(10) . . . . ? C9 C8 C13 C12 1.8(10) . . . . ? O4 C8 C13 C12 -174.6(6) . . . . ? C6 O3 C14 C19 -139.5(6) . . . . ? C6 O3 C14 C15 43.7(9) . . . . ? C19 C14 C15 C16 0.9(10) . . . . ? O3 C14 C15 C16 177.6(6) . . . . ? C14 C15 C16 C17 -0.7(10) . . . . ? C15 C16 C17 C18 -0.1(9) . . . . ? C15 C16 C17 C20 -178.4(6) . . . . ? C16 C17 C18 C19 0.8(10) . . . . ? C20 C17 C18 C19 179.1(6) . . . . ? C17 C18 C19 C14 -0.6(11) . . . . ? O3 C14 C19 C18 -177.1(6) . . . . ? C15 C14 C19 C18 -0.2(10) . . . . ? Nd1 O7 C20 O8 72.8(13) 7_646 . . . ? Nd1 O7 C20 C17 -109.8(10) 7_646 . . . ? Nd1 O8 C20 O7 9.0(12) 8_546 . . . ? Nd1 O8 C20 C17 -168.4(5) 8_546 . . . ? C18 C17 C20 O7 6.8(9) . . . . ? C16 C17 C20 O7 -174.9(6) . . . . ? C18 C17 C20 O8 -175.7(6) . . . . ? C16 C17 C20 O8 2.6(9) . . . . ? Nd1 O5 C21 O6 28.7(8) 4_656 . . . ? Nd1 O5 C21 C11 -148.1(5) 4_656 . . . ? Nd1 O6 C21 O5 -139(3) 8_556 . . . ? Nd1 O6 C21 C11 38(4) 8_556 . . . ? Nd1 O6 C21 Nd1 -116(3) 8_556 . . 4_656 ? C10 C11 C21 O5 169.0(6) . . . . ? C12 C11 C21 O5 -5.2(10) . . . . ? C10 C11 C21 O6 -8.0(10) . . . . ? C12 C11 C21 O6 177.9(6) . . . . ? C10 C11 C21 Nd1 106.8(11) . . . 4_656 ? C12 C11 C21 Nd1 -67.3(13) . . . 4_656 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.624 _refine_diff_density_min -1.222 _refine_diff_density_rms 0.136 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 1 0.250 -0.064 0.750 139.1 1.6 2 0.750 0.064 0.250 139.0 1.7 3 0.750 0.436 0.750 139.1 1.6 4 0.250 0.564 0.250 139.0 1.7 _platon_squeeze_details ; ? ; _database_code_depnum_ccdc_archive 'CCDC 927514' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_oooooo _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H23 O19 Pr2' _chemical_formula_weight 1113.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _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 29.888(6) _cell_length_b 9.0272(18) _cell_length_c 16.467(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.18(3) _cell_angle_gamma 90.00 _cell_volume 4084.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5890 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 25.01 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2180 _exptl_absorpt_coefficient_mu 2.440 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7263 _exptl_absorpt_correction_T_max 0.8287 _exptl_absorpt_process_details SADABS _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 'Rigaku 002 Saturn 944 area detector' _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 12490 _diffrn_reflns_av_R_equivalents 0.0790 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3598 _reflns_number_gt 2674 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert(Rigaku, 2009)' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics '(Rigaku, 1990) (Sheldrick, 1990)' _computing_publication_material 'Rigaku SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+27.7411P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3598 _refine_ls_number_parameters 285 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0653 _refine_ls_wR_factor_ref 0.1374 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 O5 O 0.95131(19) 0.7333(8) 0.6588(4) 0.0483(17) Uani 1 1 d . . . O8 O 0.9399(2) 0.2765(9) 0.9559(4) 0.0589(19) Uani 1 1 d . . . O9 O 0.9550(2) 0.0626(8) 0.9088(4) 0.0555(19) Uani 1 1 d . . . C1 C 0.9271(3) 0.1681(13) 0.9035(6) 0.045(2) Uani 1 1 d . . . O3 O 0.5577(2) 0.2838(8) 0.5198(4) 0.0530(18) Uani 1 1 d . . . O2 O 0.5597(2) 0.4722(8) 0.4339(4) 0.0545(18) Uani 1 1 d . . . C2 C 0.5790(3) 0.3691(12) 0.4887(6) 0.043(3) Uani 1 1 d . . . Pr1 Pr 0.997526(16) 0.83448(7) 0.90611(3) 0.0457(2) Uani 1 1 d . . . O7 O 0.9865(3) 0.5456(8) 0.9054(5) 0.075(2) Uani 1 1 d . . . O4 O 0.73071(17) 0.1318(6) 0.6709(3) 0.0313(13) Uani 1 1 d . . . C3 C 0.7333(2) 0.3334(9) 0.5788(4) 0.0255(17) Uani 1 1 d . . . H3 H 0.7668 0.3236 0.5970 0.031 Uiso 1 1 calc R . . O6 O 0.9315(2) 0.7656(8) 0.7732(4) 0.0473(17) Uani 1 1 d . . . C4 C 0.8714(3) 0.6788(9) 0.6411(5) 0.0264(18) Uani 1 1 d . . . C5 C 0.8374(3) 0.6658(9) 0.6786(5) 0.0316(18) Uani 1 1 d . . . H5 H 0.8461 0.6894 0.7379 0.038 Uiso 1 1 calc R . . C6 C 0.6338(2) 0.3544(9) 0.5184(5) 0.0279(18) Uani 1 1 d . . . C7 C 0.6590(3) 0.4526(10) 0.4884(5) 0.034(2) Uani 1 1 d . . . H7 H 0.6424 0.5251 0.4474 0.040 Uiso 1 1 calc R . . C8 C 0.8758(3) 0.1653(10) 0.8354(5) 0.0312(19) Uani 1 1 d . . . C9 C 0.7800(3) 0.1492(9) 0.7234(5) 0.0273(18) Uani 1 1 d . . . C10 C 0.8574(3) 0.6472(10) 0.5524(5) 0.037(2) Uani 1 1 d . . . H10 H 0.8795 0.6587 0.5258 0.045 Uiso 1 1 calc R . . C11 C 0.9214(3) 0.7312(10) 0.6943(5) 0.0310(19) Uani 1 1 d . . . O1 O 0.73238(18) 0.5408(6) 0.4864(3) 0.0373(15) Uani 1 1 d . . . C12 C 0.7783(3) 0.5848(9) 0.5403(5) 0.0291(19) Uani 1 1 d . . . C13 C 0.6576(3) 0.2471(9) 0.5798(5) 0.0284(19) Uani 1 1 d . . . H13 H 0.6405 0.1808 0.6001 0.034 Uiso 1 1 calc R . . C14 C 0.7082(3) 0.4426(9) 0.5190(5) 0.0267(18) Uani 1 1 d . . . C15 C 0.8450(3) 0.2798(10) 0.8276(5) 0.036(2) Uani 1 1 d . . . H15 H 0.8570 0.3649 0.8610 0.043 Uiso 1 1 calc R . . C16 C 0.7912(3) 0.6186(9) 0.6294(5) 0.031(2) Uani 1 1 d . . . H16 H 0.7686 0.6090 0.6549 0.037 Uiso 1 1 calc R . . C17 C 0.8097(3) 0.0351(9) 0.7278(5) 0.032(2) Uani 1 1 d . . . H17 H 0.7977 -0.0482 0.6927 0.038 Uiso 1 1 calc R . . C18 C 0.7972(3) 0.2739(10) 0.7726(5) 0.034(2) Uani 1 1 d . . . H18 H 0.7766 0.3533 0.7685 0.041 Uiso 1 1 calc R . . C19 C 0.7079(3) 0.2411(9) 0.6101(5) 0.0267(18) Uani 1 1 d . . . C20 C 0.8115(3) 0.5996(10) 0.5037(5) 0.036(2) Uani 1 1 d . . . H20 H 0.8028 0.5766 0.4444 0.043 Uiso 1 1 calc R . . C21 C 0.8580(3) 0.0414(10) 0.7845(5) 0.036(2) Uani 1 1 d . . . H21 H 0.8786 -0.0380 0.7883 0.043 Uiso 1 1 calc R . . O10 O 0.5000 0.4815(18) 0.2500 0.199(10) Uani 1 2 d S . . H10A H 0.5321 0.5120 0.2661 0.238 Uiso 0.50 1 calc PR . . 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 O5 0.019(3) 0.092(5) 0.029(3) 0.000(3) 0.005(3) -0.012(3) O8 0.030(3) 0.095(6) 0.037(4) -0.010(4) -0.003(3) -0.002(4) O9 0.016(3) 0.078(5) 0.057(4) 0.015(4) -0.001(3) 0.010(3) C1 0.023(4) 0.074(7) 0.027(4) 0.005(5) 0.000(4) -0.003(5) O3 0.020(3) 0.087(5) 0.051(4) 0.017(4) 0.013(3) 0.003(3) O2 0.024(3) 0.083(5) 0.050(4) 0.011(4) 0.007(3) 0.022(3) C2 0.017(4) 0.077(8) 0.035(5) -0.002(5) 0.009(4) 0.007(5) Pr1 0.0163(2) 0.0792(4) 0.0348(3) -0.0190(3) 0.00263(19) -0.0079(3) O7 0.081(6) 0.065(5) 0.063(5) 0.012(4) 0.012(4) -0.011(4) O4 0.017(3) 0.033(3) 0.035(3) 0.006(3) 0.001(2) -0.002(2) C3 0.012(3) 0.037(5) 0.022(4) -0.003(4) 0.001(3) 0.003(4) O6 0.026(3) 0.080(5) 0.026(3) -0.013(3) 0.000(3) -0.006(3) C4 0.026(4) 0.026(5) 0.021(4) 0.002(3) 0.002(3) -0.003(4) C5 0.029(4) 0.043(5) 0.022(4) 0.000(4) 0.009(3) -0.003(4) C6 0.015(4) 0.037(5) 0.029(4) -0.008(4) 0.005(3) 0.001(4) C7 0.022(4) 0.048(6) 0.022(4) 0.002(4) -0.001(3) -0.003(4) C8 0.015(4) 0.048(6) 0.024(4) -0.001(4) 0.001(3) -0.002(4) C9 0.018(4) 0.034(5) 0.023(4) 0.007(4) 0.001(3) -0.002(4) C10 0.030(4) 0.057(6) 0.029(4) -0.002(4) 0.016(4) -0.003(4) C11 0.018(4) 0.041(5) 0.023(4) 0.009(4) -0.003(3) 0.002(4) O1 0.027(3) 0.050(4) 0.022(3) 0.014(3) -0.004(2) -0.014(3) C12 0.023(4) 0.034(5) 0.025(4) 0.005(4) 0.002(3) -0.003(4) C13 0.023(4) 0.032(5) 0.026(4) -0.008(4) 0.006(3) -0.006(4) C14 0.020(4) 0.036(5) 0.018(4) -0.003(4) 0.001(3) -0.002(4) C15 0.027(4) 0.056(6) 0.019(4) -0.011(4) 0.004(3) -0.010(4) C16 0.034(5) 0.036(5) 0.030(4) -0.005(4) 0.020(4) -0.008(4) C17 0.028(4) 0.029(5) 0.032(4) 0.001(4) 0.005(4) -0.009(4) C18 0.027(4) 0.042(5) 0.027(4) -0.002(4) 0.003(4) 0.011(4) C19 0.018(4) 0.032(5) 0.025(4) -0.006(4) 0.003(3) 0.003(4) C20 0.035(5) 0.049(6) 0.018(4) -0.001(4) 0.005(4) -0.010(4) C21 0.021(4) 0.041(6) 0.039(5) 0.010(4) 0.005(4) 0.012(4) O10 0.25(2) 0.121(14) 0.089(11) 0.000 -0.074(13) 0.000 _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 O5 C11 1.247(9) . ? O5 Pr1 2.367(6) 2_756 ? O8 C1 1.260(11) . ? O8 Pr1 2.514(6) 5_767 ? O9 C1 1.247(11) . ? O9 Pr1 2.430(7) 1_545 ? O9 Pr1 2.959(7) 5_767 ? C1 C8 1.501(10) . ? C1 Pr1 3.057(8) 5_767 ? O3 C2 1.233(11) . ? O3 Pr1 2.451(6) 4_646 ? O2 C2 1.267(11) . ? O2 Pr1 2.457(6) 8_465 ? C2 C6 1.519(10) . ? Pr1 O5 2.367(6) 2_756 ? Pr1 O6 2.382(5) . ? Pr1 O9 2.430(7) 1_565 ? Pr1 O3 2.451(6) 4_656 ? Pr1 O2 2.457(6) 8_566 ? Pr1 O8 2.514(6) 5_767 ? Pr1 O7 2.628(8) . ? Pr1 O9 2.959(7) 5_767 ? Pr1 C1 3.057(8) 5_767 ? O4 C19 1.380(9) . ? O4 C9 1.394(8) . ? C3 C19 1.357(11) . ? C3 C14 1.386(10) . ? O6 C11 1.252(9) . ? C4 C10 1.382(10) . ? C4 C5 1.387(10) . ? C4 C11 1.480(10) . ? C5 C16 1.365(10) . ? C6 C7 1.374(11) . ? C6 C13 1.379(11) . ? C7 C14 1.357(10) . ? C8 C15 1.357(11) . ? C8 C21 1.372(11) . ? C9 C17 1.343(11) . ? C9 C18 1.363(11) . ? C10 C20 1.356(11) . ? O1 C12 1.367(9) . ? O1 C14 1.380(9) . ? C12 C20 1.357(11) . ? C12 C16 1.395(10) . ? C13 C19 1.385(10) . ? C15 C18 1.359(10) . ? C17 C21 1.379(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O5 Pr1 158.1(6) . 2_756 ? C1 O8 Pr1 103.1(6) . 5_767 ? C1 O9 Pr1 170.8(6) . 1_545 ? C1 O9 Pr1 82.5(5) . 5_767 ? Pr1 O9 Pr1 104.1(2) 1_545 5_767 ? O9 C1 O8 122.0(8) . . ? O9 C1 C8 119.8(9) . . ? O8 C1 C8 118.1(9) . . ? O9 C1 Pr1 73.7(5) . 5_767 ? O8 C1 Pr1 53.2(4) . 5_767 ? C8 C1 Pr1 152.9(6) . 5_767 ? C2 O3 Pr1 130.5(6) . 4_646 ? C2 O2 Pr1 139.0(6) . 8_465 ? O3 C2 O2 126.1(8) . . ? O3 C2 C6 118.7(8) . . ? O2 C2 C6 115.2(8) . . ? O5 Pr1 O6 86.2(2) 2_756 . ? O5 Pr1 O9 140.5(2) 2_756 1_565 ? O6 Pr1 O9 89.3(2) . 1_565 ? O5 Pr1 O3 146.5(3) 2_756 4_656 ? O6 Pr1 O3 86.1(2) . 4_656 ? O9 Pr1 O3 71.9(2) 1_565 4_656 ? O5 Pr1 O2 77.4(2) 2_756 8_566 ? O6 Pr1 O2 130.5(2) . 8_566 ? O9 Pr1 O2 76.0(2) 1_565 8_566 ? O3 Pr1 O2 130.4(2) 4_656 8_566 ? O5 Pr1 O8 82.6(2) 2_756 5_767 ? O6 Pr1 O8 141.2(3) . 5_767 ? O9 Pr1 O8 122.0(2) 1_565 5_767 ? O3 Pr1 O8 83.3(2) 4_656 5_767 ? O2 Pr1 O8 82.9(2) 8_566 5_767 ? O5 Pr1 O7 73.6(2) 2_756 . ? O6 Pr1 O7 71.3(2) . . ? O9 Pr1 O7 140.8(2) 1_565 . ? O3 Pr1 O7 73.1(2) 4_656 . ? O2 Pr1 O7 142.2(2) 8_566 . ? O8 Pr1 O7 69.9(2) 5_767 . ? O5 Pr1 O9 116.92(18) 2_756 5_767 ? O6 Pr1 O9 156.37(18) . 5_767 ? O9 Pr1 O9 75.9(2) 1_565 5_767 ? O3 Pr1 O9 71.97(18) 4_656 5_767 ? O2 Pr1 O9 64.2(2) 8_566 5_767 ? O8 Pr1 O9 46.4(2) 5_767 5_767 ? O7 Pr1 O9 108.9(2) . 5_767 ? O5 Pr1 C1 96.5(2) 2_756 5_767 ? O6 Pr1 C1 161.8(3) . 5_767 ? O9 Pr1 C1 99.6(3) 1_565 5_767 ? O3 Pr1 C1 81.8(2) 4_656 5_767 ? O2 Pr1 C1 67.4(2) 8_566 5_767 ? O8 Pr1 C1 23.7(2) 5_767 5_767 ? O7 Pr1 C1 92.2(3) . 5_767 ? O9 Pr1 C1 23.9(2) 5_767 5_767 ? C19 O4 C9 118.0(6) . . ? C19 C3 C14 118.6(7) . . ? C11 O6 Pr1 142.4(5) . . ? C10 C4 C5 118.9(7) . . ? C10 C4 C11 120.5(7) . . ? C5 C4 C11 120.6(7) . . ? C16 C5 C4 120.6(7) . . ? C7 C6 C13 121.3(7) . . ? C7 C6 C2 120.1(8) . . ? C13 C6 C2 118.6(8) . . ? C14 C7 C6 119.3(8) . . ? C15 C8 C21 118.5(7) . . ? C15 C8 C1 120.8(8) . . ? C21 C8 C1 120.4(8) . . ? C17 C9 C18 121.0(7) . . ? C17 C9 O4 117.5(7) . . ? C18 C9 O4 121.4(7) . . ? C20 C10 C4 120.4(7) . . ? O5 C11 O6 124.0(7) . . ? O5 C11 C4 118.0(7) . . ? O6 C11 C4 117.9(7) . . ? C12 O1 C14 118.7(6) . . ? C20 C12 O1 117.6(7) . . ? C20 C12 C16 119.8(7) . . ? O1 C12 C16 122.5(7) . . ? C6 C13 C19 117.7(8) . . ? C7 C14 O1 118.0(7) . . ? C7 C14 C3 121.0(7) . . ? O1 C14 C3 120.9(6) . . ? C8 C15 C18 121.9(8) . . ? C5 C16 C12 119.3(7) . . ? C9 C17 C21 119.9(8) . . ? C15 C18 C9 118.7(8) . . ? C3 C19 O4 121.6(6) . . ? C3 C19 C13 121.9(7) . . ? O4 C19 C13 116.4(7) . . ? C10 C20 C12 121.0(7) . . ? C8 C21 C17 119.9(8) . . ? 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 Pr1 O9 C1 O8 159(3) 1_545 . . . ? Pr1 O9 C1 O8 23.2(8) 5_767 . . . ? Pr1 O9 C1 C8 -19(4) 1_545 . . . ? Pr1 O9 C1 C8 -154.3(8) 5_767 . . . ? Pr1 O9 C1 Pr1 135(4) 1_545 . . 5_767 ? Pr1 O8 C1 O9 -28.2(10) 5_767 . . . ? Pr1 O8 C1 C8 149.4(6) 5_767 . . . ? Pr1 O3 C2 O2 -52.5(13) 4_646 . . . ? Pr1 O3 C2 C6 126.4(7) 4_646 . . . ? Pr1 O2 C2 O3 41.0(15) 8_465 . . . ? Pr1 O2 C2 C6 -137.9(7) 8_465 . . . ? O5 Pr1 O6 C11 -18.5(10) 2_756 . . . ? O9 Pr1 O6 C11 122.2(10) 1_565 . . . ? O3 Pr1 O6 C11 -165.9(10) 4_656 . . . ? O2 Pr1 O6 C11 51.5(11) 8_566 . . . ? O8 Pr1 O6 C11 -91.7(10) 5_767 . . . ? O7 Pr1 O6 C11 -92.4(10) . . . . ? O9 Pr1 O6 C11 172.9(8) 5_767 . . . ? C1 Pr1 O6 C11 -117.8(11) 5_767 . . . ? C10 C4 C5 C16 1.8(12) . . . . ? C11 C4 C5 C16 179.5(8) . . . . ? O3 C2 C6 C7 -176.7(8) . . . . ? O2 C2 C6 C7 2.3(12) . . . . ? O3 C2 C6 C13 -0.6(12) . . . . ? O2 C2 C6 C13 178.4(8) . . . . ? C13 C6 C7 C14 0.6(12) . . . . ? C2 C6 C7 C14 176.7(7) . . . . ? O9 C1 C8 C15 -179.1(8) . . . . ? O8 C1 C8 C15 3.3(13) . . . . ? Pr1 C1 C8 C15 66.8(18) 5_767 . . . ? O9 C1 C8 C21 6.2(13) . . . . ? O8 C1 C8 C21 -171.5(8) . . . . ? Pr1 C1 C8 C21 -108.0(15) 5_767 . . . ? C19 O4 C9 C17 -129.5(7) . . . . ? C19 O4 C9 C18 54.2(10) . . . . ? C5 C4 C10 C20 -2.2(13) . . . . ? C11 C4 C10 C20 -179.9(8) . . . . ? Pr1 O5 C11 O6 -75.0(16) 2_756 . . . ? Pr1 O5 C11 C4 107.7(14) 2_756 . . . ? Pr1 O6 C11 O5 -4.8(16) . . . . ? Pr1 O6 C11 C4 172.5(6) . . . . ? C10 C4 C11 O5 -6.2(12) . . . . ? C5 C4 C11 O5 176.2(8) . . . . ? C10 C4 C11 O6 176.3(8) . . . . ? C5 C4 C11 O6 -1.3(12) . . . . ? C14 O1 C12 C20 140.7(8) . . . . ? C14 O1 C12 C16 -41.2(11) . . . . ? C7 C6 C13 C19 -0.1(11) . . . . ? C2 C6 C13 C19 -176.2(7) . . . . ? C6 C7 C14 O1 178.7(7) . . . . ? C6 C7 C14 C3 1.3(12) . . . . ? C12 O1 C14 C7 148.5(8) . . . . ? C12 O1 C14 C3 -34.0(10) . . . . ? C19 C3 C14 C7 -3.7(11) . . . . ? C19 C3 C14 O1 178.9(7) . . . . ? C21 C8 C15 C18 1.4(13) . . . . ? C1 C8 C15 C18 -173.5(8) . . . . ? C4 C5 C16 C12 -0.6(13) . . . . ? C20 C12 C16 C5 -0.2(13) . . . . ? O1 C12 C16 C5 -178.2(8) . . . . ? C18 C9 C17 C21 1.8(12) . . . . ? O4 C9 C17 C21 -174.5(7) . . . . ? C8 C15 C18 C9 -0.5(13) . . . . ? C17 C9 C18 C15 -1.1(12) . . . . ? O4 C9 C18 C15 175.0(7) . . . . ? C14 C3 C19 O4 -178.8(7) . . . . ? C14 C3 C19 C13 4.3(12) . . . . ? C9 O4 C19 C3 23.0(10) . . . . ? C9 O4 C19 C13 -160.0(7) . . . . ? C6 C13 C19 C3 -2.4(12) . . . . ? C6 C13 C19 O4 -179.5(6) . . . . ? C4 C10 C20 C12 1.4(13) . . . . ? O1 C12 C20 C10 177.9(8) . . . . ? C16 C12 C20 C10 -0.2(13) . . . . ? C15 C8 C21 C17 -0.7(12) . . . . ? C1 C8 C21 C17 174.2(7) . . . . ? C9 C17 C21 C8 -0.9(12) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.968 _refine_diff_density_min -0.870 _refine_diff_density_rms 0.131 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 1 0.500 0.169 0.250 122.6 2.8 2 0.000 0.330 0.750 122.4 3.0 3 0.000 0.669 0.250 122.6 2.8 4 0.500 0.830 0.750 122.4 3.0 _platon_squeeze_details ; ? ; _database_code_depnum_ccdc_archive 'CCDC 927515' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_iop _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H11 O9 Sm' _chemical_formula_weight 557.66 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' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _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 29.862(6) _cell_length_b 9.2002(18) _cell_length_c 16.406(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.94(3) _cell_angle_gamma 90.00 _cell_volume 4150.9(14) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6444 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 25.01 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2168 _exptl_absorpt_coefficient_mu 2.880 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6886 _exptl_absorpt_correction_T_max 0.8023 _exptl_absorpt_process_details SADABS _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 'Rigaku 002 Saturn 944 area detector' _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 16277 _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3667 _reflns_number_gt 2790 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear-SM Expert(Rigaku, 2009)' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Rigaku SHELXTL (Sheldrick, 1990)' _computing_publication_material 'Rigaku SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1181P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3667 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1762 _refine_ls_wR_factor_gt 0.1665 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.003 _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 Sm1 Sm 1.002621(12) -0.16476(5) 1.09201(3) 0.0388(2) Uani 1 1 d . . . O1 O 0.93892(19) 0.0137(7) 1.0599(4) 0.0498(15) Uani 1 1 d . . . O2 O 0.94148(19) 0.2052(7) 0.9775(4) 0.0481(15) Uani 1 1 d . . . O3 O 0.76586(16) -0.0443(6) 1.0124(3) 0.0378(13) Uani 1 1 d . . . O4 O 0.76893(17) 0.3663(5) 0.8293(4) 0.0349(13) Uani 1 1 d . . . O5 O 0.54655(18) -0.2388(7) 0.8424(3) 0.0457(14) Uani 1 1 d . . . O6 O 0.56582(19) -0.2767(7) 0.7252(3) 0.0431(13) Uani 1 1 d . . . O7 O 0.5571(2) 0.2340(8) 0.5439(4) 0.0552(17) Uani 1 1 d . . . O8 O 0.54297(19) 0.4416(7) 0.5962(5) 0.0584(18) Uani 1 1 d . . . O9 O 1.0155(3) -0.4417(9) 1.0924(4) 0.070(2) Uani 1 1 d . . . C1 C 0.9197(3) 0.1169(10) 1.0082(5) 0.0405(19) Uani 1 1 d . . . C2 C 0.8396(2) 0.0413(8) 1.0094(4) 0.0318(16) Uani 1 1 d . . . H2 H 0.8555 -0.0324 1.0489 0.038 Uiso 1 1 calc R . . C3 C 0.8660(3) 0.1379(8) 0.9811(5) 0.0312(16) Uani 1 1 d . . . C4 C 0.8413(2) 0.2460(8) 0.9195(4) 0.0292(16) Uani 1 1 d . . . H4 H 0.8584 0.3106 0.8988 0.035 Uiso 1 1 calc R . . C5 C 0.7915(2) 0.2552(7) 0.8902(4) 0.0264(15) Uani 1 1 d . . . C6 C 0.7656(3) 0.1628(7) 0.9215(5) 0.0261(15) Uani 1 1 d . . . H6 H 0.7322 0.1734 0.9040 0.031 Uiso 1 1 calc R . . C7 C 0.7904(2) 0.0543(7) 0.9794(4) 0.0281(15) Uani 1 1 d . . . C8 C 0.7195(2) -0.0863(8) 0.9578(4) 0.0289(15) Uani 1 1 d . . . C9 C 0.7069(3) -0.1207(9) 0.8688(5) 0.0347(17) Uani 1 1 d . . . H9 H 0.7296 -0.1114 0.8433 0.042 Uiso 1 1 calc R . . C10 C 0.6600(3) -0.1690(7) 0.8184(5) 0.0319(17) Uani 1 1 d . . . H10 H 0.6515 -0.1921 0.7590 0.038 Uiso 1 1 calc R . . C11 C 0.6254(3) -0.1830(7) 0.8572(5) 0.0282(16) Uani 1 1 d . . . C12 C 0.6394(3) -0.1488(8) 0.9462(5) 0.0352(18) Uani 1 1 d . . . H12 H 0.6171 -0.1587 0.9727 0.042 Uiso 1 1 calc R . . C13 C 0.6861(3) -0.0999(9) 0.9965(5) 0.0365(18) Uani 1 1 d . . . H13 H 0.6948 -0.0764 1.0558 0.044 Uiso 1 1 calc R . . C14 C 0.5761(2) -0.2376(8) 0.8055(5) 0.0304(16) Uani 1 1 d . . . C15 C 0.7189(3) 0.3495(7) 0.7768(5) 0.0274(16) Uani 1 1 d . . . C16 C 0.7015(3) 0.2256(8) 0.7251(5) 0.0330(16) Uani 1 1 d . . . H16 H 0.7221 0.1487 0.7271 0.040 Uiso 1 1 calc R . . C17 C 0.6530(3) 0.2205(9) 0.6715(5) 0.0333(16) Uani 1 1 d . . . H17 H 0.6403 0.1367 0.6390 0.040 Uiso 1 1 calc R . . C18 C 0.6227(3) 0.3369(8) 0.6648(5) 0.0331(18) Uani 1 1 d . . . C19 C 0.6407(2) 0.4613(9) 0.7175(5) 0.0380(18) Uani 1 1 d . . . H19 H 0.6203 0.5392 0.7144 0.046 Uiso 1 1 calc R . . C20 C 0.6898(2) 0.4660(8) 0.7743(5) 0.0330(17) Uani 1 1 d . . . H20 H 0.7024 0.5468 0.8100 0.040 Uiso 1 1 calc R . . C21 C 0.5700(3) 0.3347(10) 0.5976(6) 0.043(2) 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 Sm1 0.0121(3) 0.0658(4) 0.0329(3) 0.01763(17) 0.0028(2) 0.00275(16) O1 0.025(3) 0.074(4) 0.048(3) 0.021(3) 0.012(3) 0.018(3) O2 0.015(3) 0.085(4) 0.043(3) 0.016(3) 0.010(2) 0.002(3) O3 0.022(3) 0.057(3) 0.027(3) 0.008(2) 0.001(2) -0.010(2) O4 0.014(2) 0.044(3) 0.035(3) 0.012(2) -0.004(2) -0.004(2) O5 0.024(3) 0.084(4) 0.031(3) 0.003(3) 0.012(2) -0.010(3) O6 0.025(3) 0.072(4) 0.027(3) -0.011(3) 0.004(2) -0.003(3) O7 0.027(3) 0.098(5) 0.031(3) -0.017(3) 0.001(2) -0.010(3) O8 0.015(3) 0.077(4) 0.070(4) 0.015(4) 0.003(3) 0.009(3) O9 0.065(4) 0.084(5) 0.053(4) -0.010(3) 0.014(3) 0.018(4) C1 0.020(4) 0.067(5) 0.034(4) 0.002(4) 0.010(3) 0.006(4) C2 0.025(4) 0.044(4) 0.024(3) 0.007(3) 0.007(3) 0.000(3) C3 0.022(4) 0.043(4) 0.026(4) 0.001(3) 0.006(3) 0.005(3) C4 0.017(3) 0.040(4) 0.028(4) 0.002(3) 0.007(3) -0.005(3) C5 0.017(3) 0.039(4) 0.018(3) -0.001(3) 0.001(3) 0.003(3) C6 0.012(3) 0.038(4) 0.024(4) -0.004(3) 0.002(3) 0.000(3) C7 0.025(4) 0.035(4) 0.021(3) -0.001(3) 0.006(3) -0.007(3) C8 0.022(4) 0.037(4) 0.026(3) 0.009(3) 0.007(3) -0.004(3) C9 0.027(4) 0.051(4) 0.031(4) -0.004(3) 0.017(3) -0.008(3) C10 0.027(4) 0.046(5) 0.022(4) -0.003(3) 0.009(3) -0.004(3) C11 0.018(4) 0.042(4) 0.023(4) 0.003(3) 0.006(3) 0.000(3) C12 0.026(4) 0.060(5) 0.022(4) 0.000(3) 0.012(3) -0.007(3) C13 0.026(4) 0.064(5) 0.016(3) -0.005(3) 0.005(3) -0.011(4) C14 0.021(4) 0.038(4) 0.026(4) 0.003(3) 0.003(3) 0.001(3) C15 0.017(4) 0.036(4) 0.023(3) 0.011(3) 0.000(3) 0.002(3) C16 0.024(4) 0.043(4) 0.026(4) -0.003(3) 0.003(3) 0.005(3) C17 0.025(4) 0.046(4) 0.025(4) -0.010(3) 0.006(3) -0.001(3) C18 0.014(4) 0.057(5) 0.026(4) 0.006(3) 0.004(3) 0.003(3) C19 0.017(4) 0.049(5) 0.038(4) 0.003(4) 0.001(3) 0.010(3) C20 0.021(4) 0.037(4) 0.032(4) -0.001(3) 0.000(3) 0.001(3) C21 0.020(4) 0.075(6) 0.031(4) -0.001(4) 0.006(3) -0.004(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 Sm1 O5 2.309(5) 7_647 ? Sm1 O6 2.326(5) 8_546 ? Sm1 O8 2.368(7) 8_556 ? Sm1 O2 2.389(6) 5_757 ? Sm1 O1 2.411(5) . ? Sm1 O7 2.433(6) 4_646 ? Sm1 O9 2.576(8) . ? O1 C1 1.253(10) . ? O2 C1 1.262(10) . ? O2 Sm1 2.389(6) 5_757 ? O3 C8 1.378(8) . ? O3 C7 1.400(8) . ? O4 C5 1.404(8) . ? O4 C15 1.412(8) . ? O5 C14 1.249(9) . ? O5 Sm1 2.309(5) 7_647 ? O6 C14 1.282(9) . ? O6 Sm1 2.326(5) 8_445 ? O7 C21 1.232(11) . ? O7 Sm1 2.433(6) 4_656 ? O8 C21 1.267(10) . ? O8 Sm1 2.368(7) 8_455 ? C1 C3 1.502(10) . ? C2 C7 1.361(10) . ? C2 C3 1.382(10) . ? C2 H2 0.9300 . ? C3 C4 1.404(10) . ? C4 C5 1.375(9) . ? C4 H4 0.9300 . ? C5 C6 1.377(10) . ? C6 C7 1.378(10) . ? C6 H6 0.9300 . ? C8 C13 1.380(10) . ? C8 C9 1.396(10) . ? C9 C10 1.391(10) . ? C9 H9 0.9300 . ? C10 C11 1.417(11) . ? C10 H10 0.9300 . ? C11 C12 1.389(10) . ? C11 C14 1.473(10) . ? C12 C13 1.391(10) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C15 C20 1.372(10) . ? C15 C16 1.395(10) . ? C16 C17 1.369(10) . ? C16 H16 0.9300 . ? C17 C18 1.380(10) . ? C17 H17 0.9300 . ? C18 C19 1.408(11) . ? C18 C21 1.529(10) . ? C19 C20 1.397(9) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 O5 Sm1 O6 84.50(19) 7_647 8_546 ? O5 Sm1 O8 136.7(2) 7_647 8_556 ? O6 Sm1 O8 87.5(2) 8_546 8_556 ? O5 Sm1 O2 148.4(2) 7_647 5_757 ? O6 Sm1 O2 87.1(2) 8_546 5_757 ? O8 Sm1 O2 72.9(2) 8_556 5_757 ? O5 Sm1 O1 76.9(2) 7_647 . ? O6 Sm1 O1 130.2(2) 8_546 . ? O8 Sm1 O1 76.4(2) 8_556 . ? O2 Sm1 O1 129.8(2) 5_757 . ? O5 Sm1 O7 84.7(2) 7_647 4_646 ? O6 Sm1 O7 144.0(2) 8_546 4_646 ? O8 Sm1 O7 122.8(2) 8_556 4_646 ? O2 Sm1 O7 84.3(2) 5_757 4_646 ? O1 Sm1 O7 80.0(2) . 4_646 ? O5 Sm1 O9 74.9(2) 7_647 . ? O6 Sm1 O9 72.7(2) 8_546 . ? O8 Sm1 O9 141.6(2) 8_556 . ? O2 Sm1 O9 73.5(2) 5_757 . ? O1 Sm1 O9 141.1(2) . . ? O7 Sm1 O9 71.2(2) 4_646 . ? C1 O1 Sm1 141.1(6) . . ? C1 O2 Sm1 130.9(6) . 5_757 ? C8 O3 C7 118.3(5) . . ? C5 O4 C15 117.1(5) . . ? C14 O5 Sm1 157.8(6) . 7_647 ? C14 O6 Sm1 144.2(5) . 8_445 ? C21 O7 Sm1 106.3(6) . 4_656 ? C21 O8 Sm1 170.7(6) . 8_455 ? O1 C1 O2 126.0(7) . . ? O1 C1 C3 116.9(7) . . ? O2 C1 C3 117.1(7) . . ? C7 C2 C3 119.8(7) . . ? C7 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 119.3(7) . . ? C2 C3 C1 120.0(7) . . ? C4 C3 C1 120.3(7) . . ? C5 C4 C3 119.2(7) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.3(6) . . ? C4 C5 O4 116.6(6) . . ? C6 C5 O4 122.1(6) . . ? C5 C6 C7 118.4(6) . . ? C5 C6 H6 120.8 . . ? C7 C6 H6 120.8 . . ? C2 C7 C6 121.8(7) . . ? C2 C7 O3 117.1(6) . . ? C6 C7 O3 121.0(6) . . ? O3 C8 C13 116.7(6) . . ? O3 C8 C9 122.5(6) . . ? C13 C8 C9 120.7(6) . . ? C10 C9 C8 119.6(7) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 120.2(7) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 118.7(7) . . ? C12 C11 C14 120.4(7) . . ? C10 C11 C14 120.9(7) . . ? C11 C12 C13 121.1(7) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C8 C13 C12 119.7(7) . . ? C8 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? O5 C14 O6 124.4(6) . . ? O5 C14 C11 117.3(6) . . ? O6 C14 C11 118.2(7) . . ? C20 C15 C16 122.5(6) . . ? C20 C15 O4 116.1(6) . . ? C16 C15 O4 121.1(6) . . ? C17 C16 C15 118.0(7) . . ? C17 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? C16 C17 C18 121.4(7) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C17 C18 C19 119.9(7) . . ? C17 C18 C21 120.4(7) . . ? C19 C18 C21 119.6(7) . . ? C20 C19 C18 119.1(7) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? C15 C20 C19 118.9(7) . . ? C15 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? O7 C21 O8 123.4(8) . . ? O7 C21 C18 118.3(8) . . ? O8 C21 C18 118.1(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Sm1 O1 C1 -160.6(9) 7_647 . . . ? O6 Sm1 O1 C1 128.5(9) 8_546 . . . ? O8 Sm1 O1 C1 53.8(9) 8_556 . . . ? O2 Sm1 O1 C1 0.2(10) 5_757 . . . ? O7 Sm1 O1 C1 -73.7(9) 4_646 . . . ? O9 Sm1 O1 C1 -116.2(9) . . . . ? Sm1 O1 C1 O2 -35.0(15) . . . . ? Sm1 O1 C1 C3 145.5(6) . . . . ? Sm1 O2 C1 O1 49.1(12) 5_757 . . . ? Sm1 O2 C1 C3 -131.4(6) 5_757 . . . ? C7 C2 C3 C4 -1.8(11) . . . . ? C7 C2 C3 C1 -175.0(7) . . . . ? O1 C1 C3 C2 -3.3(12) . . . . ? O2 C1 C3 C2 177.3(8) . . . . ? O1 C1 C3 C4 -176.4(7) . . . . ? O2 C1 C3 C4 4.1(12) . . . . ? C2 C3 C4 C5 1.4(11) . . . . ? C1 C3 C4 C5 174.6(7) . . . . ? C3 C4 C5 C6 1.5(11) . . . . ? C3 C4 C5 O4 179.4(6) . . . . ? C15 O4 C5 C4 159.4(7) . . . . ? C15 O4 C5 C6 -22.7(10) . . . . ? C4 C5 C6 C7 -3.9(10) . . . . ? O4 C5 C6 C7 178.3(6) . . . . ? C3 C2 C7 C6 -0.6(11) . . . . ? C3 C2 C7 O3 -178.3(7) . . . . ? C5 C6 C7 C2 3.4(11) . . . . ? C5 C6 C7 O3 -179.0(6) . . . . ? C8 O3 C7 C2 -147.8(7) . . . . ? C8 O3 C7 C6 34.5(10) . . . . ? C7 O3 C8 C13 -140.1(7) . . . . ? C7 O3 C8 C9 43.0(10) . . . . ? O3 C8 C9 C10 176.9(7) . . . . ? C13 C8 C9 C10 0.1(12) . . . . ? C8 C9 C10 C11 0.1(11) . . . . ? C9 C10 C11 C12 -0.5(10) . . . . ? C9 C10 C11 C14 -178.3(7) . . . . ? C10 C11 C12 C13 0.8(11) . . . . ? C14 C11 C12 C13 178.7(7) . . . . ? O3 C8 C13 C12 -176.8(7) . . . . ? C9 C8 C13 C12 0.2(12) . . . . ? C11 C12 C13 C8 -0.7(12) . . . . ? Sm1 O5 C14 O6 72.6(15) 7_647 . . . ? Sm1 O5 C14 C11 -109.5(12) 7_647 . . . ? Sm1 O6 C14 O5 11.7(14) 8_445 . . . ? Sm1 O6 C14 C11 -166.1(6) 8_445 . . . ? C12 C11 C14 O5 6.5(11) . . . . ? C10 C11 C14 O5 -175.7(7) . . . . ? C12 C11 C14 O6 -175.5(7) . . . . ? C10 C11 C14 O6 2.2(10) . . . . ? C5 O4 C15 C20 129.9(7) . . . . ? C5 O4 C15 C16 -55.2(10) . . . . ? C20 C15 C16 C17 -1.3(12) . . . . ? O4 C15 C16 C17 -175.9(7) . . . . ? C15 C16 C17 C18 3.4(12) . . . . ? C16 C17 C18 C19 -3.6(12) . . . . ? C16 C17 C18 C21 173.7(8) . . . . ? C17 C18 C19 C20 1.6(12) . . . . ? C21 C18 C19 C20 -175.7(7) . . . . ? C16 C15 C20 C19 -0.6(12) . . . . ? O4 C15 C20 C19 174.3(7) . . . . ? C18 C19 C20 C15 0.4(12) . . . . ? Sm1 O7 C21 O8 28.8(10) 4_656 . . . ? Sm1 O7 C21 C18 -146.3(6) 4_656 . . . ? Sm1 O8 C21 O7 -123(3) 8_455 . . . ? Sm1 O8 C21 C18 52(4) 8_455 . . . ? C17 C18 C21 O7 -7.4(12) . . . . ? C19 C18 C21 O7 169.9(8) . . . . ? C17 C18 C21 O8 177.2(8) . . . . ? C19 C18 C21 O8 -5.5(12) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 3.265 _refine_diff_density_min -2.729 _refine_diff_density_rms 0.197 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 1 0.500 -0.184 0.250 144.6 23.1 2 0.500 0.184 0.750 144.7 23.6 3 0.000 0.316 0.250 144.6 23.1 4 0.000 0.684 0.750 144.7 23.6 _platon_squeeze_details ; ? ; _database_code_depnum_ccdc_archive 'CCDC 927516'