# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Yong Xing' _publ_contact_author_email YHXING2000@YAHOO.COM _publ_section_title ; Synthesis, Structure and Luminescent Properties of Coordination Polymers with 1,2-Benzenedicarboxylate and Series of Flexible Dicarboxylate ligands ; loop_ _publ_author_name 'Yong Xing' 'Mao-Fa Ge' 'Shuyun Niu' 'Li Xian Sun' 'Zhuo Wang' 'Chun-Guang Wang' 'Jian Zhang' # Attachment '1.cif' data_hkl-71 _database_code_depnum_ccdc_archive 'CCDC 725100' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 O8.50 Tb' _chemical_formula_weight 412.09 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' Tb Tb -0.1723 4.1537 '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 19.5036(18) _cell_length_b 5.9798(5) _cell_length_c 20.4223(18) _cell_angle_alpha 90.00 _cell_angle_beta 110.8680(10) _cell_angle_gamma 90.00 _cell_volume 2225.6(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1953 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5257 _exptl_absorpt_coefficient_mu 6.393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3198 _exptl_absorpt_correction_T_max 0.7662 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5257 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1953 _reflns_number_gt 1762 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0252P)^2^+2.4463P] 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 1953 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0227 _refine_ls_wR_factor_ref 0.0530 _refine_ls_wR_factor_gt 0.0513 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H3WA H 0.535(3) 0.775(11) 0.271(3) 0.06(2) Uiso 1 1 d . . . Tb1 Tb 0.362790(10) 0.82901(3) 0.031933(10) 0.01183(9) Uani 1 1 d . . . C1 C 0.2466(2) 0.5234(7) 0.0996(2) 0.0133(9) Uani 1 1 d . . . C2 C 0.2972(2) 0.4668(7) 0.1721(2) 0.0149(9) Uani 1 1 d . . . C3 C 0.2973(3) 0.6175(8) 0.2245(2) 0.0222(11) Uani 1 1 d . . . H3A H 0.2679 0.7437 0.2128 0.033 Uiso 1 1 d R . . C4 C 0.3397(3) 0.5761(9) 0.2937(2) 0.0247(11) Uani 1 1 d . . . H4A H 0.3393 0.6771 0.3281 0.037 Uiso 1 1 d R . . C5 C 0.3830(3) 0.3863(9) 0.3114(2) 0.0255(12) Uani 1 1 d . . . H5A H 0.4108 0.3582 0.3581 0.038 Uiso 1 1 d R . . C6 C 0.3843(3) 0.2397(8) 0.2602(2) 0.0213(10) Uani 1 1 d . . . H6A H 0.4137 0.1139 0.2724 0.032 Uiso 1 1 d R . . C7 C 0.3422(2) 0.2766(8) 0.1894(2) 0.0162(10) Uani 1 1 d . . . C8 C 0.3475(2) 0.1203(7) 0.1351(2) 0.0141(9) Uiso 1 1 d . . . C9 C 0.4989(2) 1.1114(7) 0.0181(2) 0.0146(10) Uani 1 1 d . . . O1W O 0.44175(17) 0.5580(6) 0.10772(16) 0.0281(8) Uani 1 1 d . . . H13B H 0.4549 0.4589 0.0991 0.042 Uiso 1 1 d R . . H13A H 0.4566 0.6097 0.1492 0.042 Uiso 1 1 d R . . O1 O 0.26883(16) 0.6478(5) 0.06050(15) 0.0176(7) Uani 1 1 d . . . O2W O 0.33576(16) 0.4989(5) -0.03625(16) 0.0232(7) Uani 1 1 d . . . H11B H 0.3554 0.4334 -0.0385 0.035 Uiso 1 1 d R . . H11A H 0.2904 0.4648 -0.0464 0.035 Uiso 1 1 d R . . O2 O 0.18026(16) 0.4648(5) 0.07896(15) 0.0190(7) Uani 1 1 d . . . O3W O 0.5000 0.6940(10) 0.2500 0.0354(14) Uani 1 2 d S . . O3 O 0.39354(17) -0.0391(5) 0.15222(16) 0.0215(7) Uiso 1 1 d . . . O4 O 0.30659(16) 0.1453(5) 0.07134(15) 0.0156(7) Uiso 1 1 d . . . O5 O 0.45064(17) 1.1322(5) 0.04566(16) 0.0203(7) Uani 1 1 d . . . O6 O 0.54462(17) 1.2549(6) 0.01740(16) 0.0193(7) Uiso 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 Tb1 0.01105(13) 0.01216(14) 0.01243(13) -0.00033(8) 0.00434(9) -0.00035(8) C1 0.015(2) 0.011(2) 0.015(2) 0.0008(18) 0.0082(19) 0.0031(18) C2 0.017(2) 0.017(3) 0.012(2) 0.0025(18) 0.0071(19) -0.0030(18) C3 0.023(3) 0.020(3) 0.023(3) -0.003(2) 0.007(2) 0.000(2) C4 0.028(3) 0.029(3) 0.018(3) -0.007(2) 0.009(2) -0.002(2) C5 0.023(3) 0.041(3) 0.010(2) 0.001(2) 0.002(2) 0.005(2) C6 0.024(3) 0.020(3) 0.019(2) 0.004(2) 0.005(2) 0.005(2) C7 0.015(2) 0.016(3) 0.015(2) 0.0023(18) 0.0032(19) -0.0021(18) C9 0.009(2) 0.020(3) 0.013(2) 0.0002(19) 0.0014(19) 0.0003(18) O1W 0.033(2) 0.025(2) 0.0217(18) -0.0046(15) 0.0048(16) 0.0117(15) O1 0.0195(17) 0.0186(18) 0.0160(16) 0.0051(13) 0.0081(14) -0.0023(13) O2W 0.0171(17) 0.0197(18) 0.0339(19) -0.0060(15) 0.0104(15) -0.0011(14) O2 0.0150(17) 0.0235(19) 0.0179(16) 0.0026(14) 0.0050(14) -0.0005(13) O3W 0.031(3) 0.041(4) 0.025(3) 0.000 -0.002(3) 0.000 O5 0.0183(17) 0.0213(19) 0.0251(18) -0.0065(14) 0.0121(15) -0.0040(13) _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 Tb1 O2W 2.364(3) . ? Tb1 O1 2.374(3) . ? Tb1 O1W 2.386(3) . ? Tb1 O6 2.413(3) 5_675 ? Tb1 O5 2.441(3) . ? Tb1 O3 2.443(3) 1_565 ? Tb1 O2 2.449(3) 7_565 ? Tb1 O4 2.461(3) 1_565 ? Tb1 O1 2.592(3) 7_565 ? Tb1 C8 2.830(4) 1_565 ? Tb1 C1 2.909(4) 7_565 ? C1 O2 1.259(5) . ? C1 O1 1.275(5) . ? C1 C2 1.496(6) . ? C1 Tb1 2.909(4) 7_565 ? C2 C3 1.399(6) . ? C2 C7 1.402(6) . ? C3 C4 1.382(6) . ? C3 H3A 0.9252 . ? C4 C5 1.383(7) . ? C4 H4A 0.9285 . ? C5 C6 1.372(7) . ? C5 H5A 0.9292 . ? C6 C7 1.402(6) . ? C6 H6A 0.9248 . ? C7 C8 1.482(6) . ? C8 O4 1.270(5) . ? C8 O3 1.270(5) . ? C8 Tb1 2.830(4) 1_545 ? C9 O6 1.241(5) . ? C9 O5 1.264(5) . ? C9 C9 1.532(9) 5_675 ? O1W H13B 0.6923 . ? O1W H13A 0.8506 . ? O1 Tb1 2.592(3) 7_565 ? O2W H11B 0.5613 . ? O2W H11A 0.8573 . ? O2 Tb1 2.449(3) 7_565 ? O3W H3WA 0.82(6) . ? O3 Tb1 2.443(3) 1_545 ? O4 Tb1 2.461(3) 1_545 ? O6 Tb1 2.413(3) 5_675 ? 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 O2W Tb1 O1 74.57(10) . . ? O2W Tb1 O1W 76.82(11) . . ? O1 Tb1 O1W 84.67(11) . . ? O2W Tb1 O6 67.89(10) . 5_675 ? O1 Tb1 O6 139.97(11) . 5_675 ? O1W Tb1 O6 73.95(11) . 5_675 ? O2W Tb1 O5 133.45(10) . . ? O1 Tb1 O5 151.95(10) . . ? O1W Tb1 O5 99.52(11) . . ? O6 Tb1 O5 66.63(10) 5_675 . ? O2W Tb1 O3 141.74(11) . 1_565 ? O1 Tb1 O3 80.49(10) . 1_565 ? O1W Tb1 O3 72.34(11) . 1_565 ? O6 Tb1 O3 122.33(10) 5_675 1_565 ? O5 Tb1 O3 74.56(10) . 1_565 ? O2W Tb1 O2 86.83(10) . 7_565 ? O1 Tb1 O2 114.62(10) . 7_565 ? O1W Tb1 O2 150.57(11) . 7_565 ? O6 Tb1 O2 77.27(10) 5_675 7_565 ? O5 Tb1 O2 74.20(10) . 7_565 ? O3 Tb1 O2 130.37(11) 1_565 7_565 ? O2W Tb1 O4 143.36(10) . 1_565 ? O1 Tb1 O4 78.32(10) . 1_565 ? O1W Tb1 O4 124.72(10) . 1_565 ? O6 Tb1 O4 141.55(10) 5_675 1_565 ? O5 Tb1 O4 76.58(10) . 1_565 ? O3 Tb1 O4 53.22(10) 1_565 1_565 ? O2 Tb1 O4 82.50(10) 7_565 1_565 ? O2W Tb1 O1 70.16(10) . 7_565 ? O1 Tb1 O1 63.41(11) . 7_565 ? O1W Tb1 O1 138.72(10) . 7_565 ? O6 Tb1 O1 113.66(10) 5_675 7_565 ? O5 Tb1 O1 121.09(10) . 7_565 ? O3 Tb1 O1 122.67(10) 1_565 7_565 ? O2 Tb1 O1 51.35(9) 7_565 7_565 ? O4 Tb1 O1 75.89(10) 1_565 7_565 ? O2W Tb1 C8 153.10(11) . 1_565 ? O1 Tb1 C8 78.63(11) . 1_565 ? O1W Tb1 C8 98.63(12) . 1_565 ? O6 Tb1 C8 137.03(11) 5_675 1_565 ? O5 Tb1 C8 73.33(11) . 1_565 ? O3 Tb1 C8 26.60(11) 1_565 1_565 ? O2 Tb1 C8 106.62(11) 7_565 1_565 ? O4 Tb1 C8 26.62(11) 1_565 1_565 ? O1 Tb1 C8 99.76(11) 7_565 1_565 ? O2W Tb1 C1 76.89(11) . 7_565 ? O1 Tb1 C1 89.38(11) . 7_565 ? O1W Tb1 C1 153.69(12) . 7_565 ? O6 Tb1 C1 95.11(11) 5_675 7_565 ? O5 Tb1 C1 97.73(12) . 7_565 ? O3 Tb1 C1 131.86(11) 1_565 7_565 ? O2 Tb1 C1 25.36(10) 7_565 7_565 ? O4 Tb1 C1 78.66(11) 1_565 7_565 ? O1 Tb1 C1 26.00(10) 7_565 7_565 ? C8 Tb1 C1 105.28(12) 1_565 7_565 ? O2 C1 O1 119.4(4) . . ? O2 C1 C2 120.3(4) . . ? O1 C1 C2 120.0(4) . . ? O2 C1 Tb1 56.5(2) . 7_565 ? O1 C1 Tb1 63.0(2) . 7_565 ? C2 C1 Tb1 172.1(3) . 7_565 ? C3 C2 C7 119.9(4) . . ? C3 C2 C1 115.6(4) . . ? C7 C2 C1 124.5(4) . . ? C4 C3 C2 120.2(5) . . ? C4 C3 H3A 120.1 . . ? C2 C3 H3A 119.7 . . ? C3 C4 C5 120.1(4) . . ? C3 C4 H4A 119.6 . . ? C5 C4 H4A 120.3 . . ? C6 C5 C4 120.0(4) . . ? C6 C5 H5A 120.3 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C7 121.5(5) . . ? C5 C6 H6A 119.4 . . ? C7 C6 H6A 119.1 . . ? C6 C7 C2 118.2(4) . . ? C6 C7 C8 120.1(4) . . ? C2 C7 C8 121.8(4) . . ? O4 C8 O3 119.7(4) . . ? O4 C8 C7 120.5(4) . . ? O3 C8 C7 119.9(4) . . ? O4 C8 Tb1 60.3(2) . 1_545 ? O3 C8 Tb1 59.4(2) . 1_545 ? C7 C8 Tb1 177.9(3) . 1_545 ? O6 C9 O5 126.1(4) . . ? O6 C9 C9 116.9(5) . 5_675 ? O5 C9 C9 116.9(5) . 5_675 ? Tb1 O1W H13B 128.9 . . ? Tb1 O1W H13A 108.2 . . ? H13B O1W H13A 122.6 . . ? C1 O1 Tb1 152.2(3) . . ? C1 O1 Tb1 91.0(2) . 7_565 ? Tb1 O1 Tb1 116.59(11) . 7_565 ? Tb1 O2W H11B 128.0 . . ? Tb1 O2W H11A 109.6 . . ? H11B O2W H11A 119.4 . . ? C1 O2 Tb1 98.2(3) . 7_565 ? C8 O3 Tb1 94.0(3) . 1_545 ? C8 O4 Tb1 93.1(2) . 1_545 ? C9 O5 Tb1 118.7(3) . . ? C9 O6 Tb1 120.5(3) . 5_675 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.731 _refine_diff_density_min -0.789 _refine_diff_density_rms 0.139 # Attachment '2.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 725101' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H9 O8.50 Sm' _chemical_formula_weight 403.52 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 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 19.694(3) _cell_length_b 6.0192(9) _cell_length_c 20.467(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.995(2) _cell_angle_gamma 90.00 _cell_volume 2265.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6670 _cell_measurement_theta_min 2.13 _cell_measurement_theta_max 29.02 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 5.222 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5924 _exptl_absorpt_correction_T_max 0.7178 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5301 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1988 _reflns_number_gt 1827 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0233P)^2^+0.7747P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1988 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0207 _refine_ls_R_factor_gt 0.0185 _refine_ls_wR_factor_ref 0.0452 _refine_ls_wR_factor_gt 0.0442 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 Sm Sm 0.362664(8) -0.17015(3) 0.032561(8) 0.01295(7) Uani 1 1 d . . . C1 C 0.34668(17) 0.1224(6) 0.13644(17) 0.0177(7) Uani 1 1 d . . . C2 C 0.34174(17) 0.2814(6) 0.19091(17) 0.0172(7) Uani 1 1 d . . . C3 C 0.38373(19) 0.2444(6) 0.26073(18) 0.0233(8) Uani 1 1 d . . . H3 H 0.4132 0.1190 0.2732 0.028 Uiso 1 1 calc R . . C4 C 0.38217(19) 0.3929(7) 0.31212(18) 0.0276(9) Uani 1 1 d . . . H4 H 0.4100 0.3653 0.3588 0.033 Uiso 1 1 calc R . . C5 C 0.3396(2) 0.5804(7) 0.29430(18) 0.0268(8) Uani 1 1 d . . . H5 H 0.3395 0.6816 0.3286 0.032 Uiso 1 1 calc R . . C6 C 0.29664(19) 0.6180(6) 0.22447(18) 0.0226(8) Uani 1 1 d . . . H6A H 0.2676 0.7442 0.2125 0.027 Uiso 1 1 calc R . . C7 C 0.29663(16) 0.4695(5) 0.17253(16) 0.0162(7) Uani 1 1 d . . . C8 C 0.24615(15) 0.5229(5) 0.10030(15) 0.0136(6) Uiso 1 1 d . . . C9 C 0.49912(17) 0.1120(6) 0.01802(16) 0.0162(7) Uani 1 1 d . . . O1W O 0.33619(12) -0.5055(4) -0.03647(12) 0.0254(5) Uani 1 1 d . . . H1WB H 0.3622 -0.5934 -0.0366 0.038 Uiso 1 1 d R . . H1WA H 0.2958 -0.5644 -0.0450 0.038 Uiso 1 1 d R . . O1 O 0.30591(12) 0.1474(4) 0.07290(11) 0.0173(5) Uani 1 1 d . . . O2W O 0.44213(13) -0.4453(4) 0.11016(12) 0.0299(6) Uani 1 1 d . . . H2WA H 0.4685 -0.4090 0.1503 0.045 Uiso 1 1 d R . . H2WB H 0.4517 -0.5604 0.0972 0.045 Uiso 1 1 d R . . O2 O 0.39280(12) -0.0337(4) 0.15387(12) 0.0254(6) Uani 1 1 d . . . O3W O 0.5000 0.7024(6) 0.2500 0.0356(9) Uani 1 2 d S . . H1 H 0.4657 0.7920 0.2301 0.053 Uiso 1 1 d R . . O3 O 0.26799(12) 0.6456(3) 0.06118(12) 0.0177(5) Uiso 1 1 d . . . O4 O 0.18103(12) 0.4619(4) 0.08048(11) 0.0214(5) Uiso 1 1 d . . . O5 O 0.45141(12) 0.1330(4) 0.04551(13) 0.0227(5) Uani 1 1 d . . . O6 O 0.54400(12) 0.2538(4) 0.01680(13) 0.0233(5) 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 Sm 0.01191(10) 0.01265(11) 0.01530(11) -0.00035(6) 0.00611(7) -0.00054(6) C1 0.0159(16) 0.0181(19) 0.0212(19) 0.0011(14) 0.0091(14) -0.0011(14) C2 0.0211(18) 0.0159(18) 0.0145(17) -0.0003(14) 0.0063(14) -0.0017(14) C3 0.0268(19) 0.022(2) 0.0196(19) 0.0027(15) 0.0066(15) 0.0089(16) C4 0.029(2) 0.040(2) 0.0124(18) 0.0000(16) 0.0057(15) 0.0015(17) C5 0.033(2) 0.029(2) 0.0208(19) -0.0061(16) 0.0119(16) -0.0005(17) C6 0.0263(19) 0.0207(19) 0.0227(19) -0.0034(15) 0.0109(15) 0.0014(15) C7 0.0157(15) 0.0173(18) 0.0183(17) 0.0021(14) 0.0093(13) -0.0041(13) C9 0.0126(15) 0.0175(18) 0.0177(17) -0.0009(14) 0.0046(13) 0.0015(13) O1W 0.0197(12) 0.0202(13) 0.0389(14) -0.0095(12) 0.0138(11) -0.0032(11) O1 0.0191(12) 0.0165(13) 0.0154(12) -0.0004(9) 0.0051(10) 0.0004(9) O2W 0.0343(14) 0.0273(15) 0.0240(13) -0.0021(11) 0.0055(11) 0.0120(11) O2 0.0285(13) 0.0238(15) 0.0207(12) 0.0005(11) 0.0050(10) 0.0107(11) O3W 0.035(2) 0.036(2) 0.027(2) 0.000 -0.0009(17) 0.000 O5 0.0207(12) 0.0219(14) 0.0309(14) -0.0088(11) 0.0158(11) -0.0058(10) O6 0.0209(13) 0.0183(13) 0.0361(15) -0.0076(11) 0.0170(11) -0.0072(11) _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 Sm O1W 2.411(2) . ? Sm O3 2.415(2) 1_545 ? Sm O2W 2.436(2) . ? Sm O6 2.446(2) 5_655 ? Sm O5 2.474(2) . ? Sm O2 2.477(2) . ? Sm O4 2.498(2) 7 ? Sm O1 2.499(2) . ? Sm O3 2.605(2) 7 ? Sm C1 2.863(3) . ? Sm C8 2.932(3) 7 ? C1 O2 1.266(4) . ? C1 O1 1.269(4) . ? C1 C2 1.499(5) . ? C2 C3 1.389(5) . ? C2 C7 1.404(5) . ? C3 C4 1.389(5) . ? C3 H3 0.9300 . ? C4 C5 1.375(5) . ? C4 H4 0.9300 . ? C5 C6 1.394(5) . ? C5 H5 0.9300 . ? C6 C7 1.389(5) . ? C6 H6A 0.9300 . ? C7 C8 1.491(4) . ? C8 O4 1.254(4) . ? C8 O3 1.272(4) . ? C8 Sm 2.932(3) 7 ? C9 O6 1.235(4) . ? C9 O5 1.263(4) . ? C9 C9 1.544(6) 5_655 ? O1W H1WB 0.7377 . ? O1W H1WA 0.8311 . ? O2W H2WA 0.8289 . ? O2W H2WB 0.7883 . ? O3W H1 0.8460 . ? O3 Sm 2.415(2) 1_565 ? O3 Sm 2.605(2) 7 ? O4 Sm 2.498(2) 7 ? O6 Sm 2.446(2) 5_655 ? 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 O1W Sm O3 74.58(7) . 1_545 ? O1W Sm O2W 76.49(8) . . ? O3 Sm O2W 84.33(8) 1_545 . ? O1W Sm O6 67.82(7) . 5_655 ? O3 Sm O6 139.94(8) 1_545 5_655 ? O2W Sm O6 74.16(8) . 5_655 ? O1W Sm O5 132.55(7) . . ? O3 Sm O5 152.84(7) 1_545 . ? O2W Sm O5 99.64(8) . . ? O6 Sm O5 65.77(8) 5_655 . ? O1W Sm O2 142.08(8) . . ? O3 Sm O2 80.66(8) 1_545 . ? O2W Sm O2 72.83(8) . . ? O6 Sm O2 122.45(8) 5_655 . ? O5 Sm O2 75.03(8) . . ? O1W Sm O4 86.95(8) . 7 ? O3 Sm O4 114.54(7) 1_545 7 ? O2W Sm O4 150.79(8) . 7 ? O6 Sm O4 77.36(8) 5_655 7 ? O5 Sm O4 74.03(8) . 7 ? O2 Sm O4 129.89(8) . 7 ? O1W Sm O1 143.65(7) . . ? O3 Sm O1 78.20(7) 1_545 . ? O2W Sm O1 124.30(8) . . ? O6 Sm O1 141.72(8) 5_655 . ? O5 Sm O1 77.46(7) . . ? O2 Sm O1 52.42(7) . . ? O4 Sm O1 82.86(7) 7 . ? O1W Sm O3 70.53(7) . 7 ? O3 Sm O3 63.89(9) 1_545 7 ? O2W Sm O3 138.86(8) . 7 ? O6 Sm O3 113.43(7) 5_655 7 ? O5 Sm O3 120.69(8) . 7 ? O2 Sm O3 122.55(7) . 7 ? O4 Sm O3 50.78(7) 7 7 ? O1 Sm O3 76.07(7) . 7 ? O1W Sm C1 153.07(8) . . ? O3 Sm C1 78.61(8) 1_545 . ? O2W Sm C1 98.62(9) . . ? O6 Sm C1 137.05(8) 5_655 . ? O5 Sm C1 74.24(8) . . ? O2 Sm C1 26.16(8) . . ? O4 Sm C1 106.63(9) 7 . ? O1 Sm C1 26.27(8) . . ? O3 Sm C1 99.77(8) 7 . ? O1W Sm C8 77.10(8) . 7 ? O3 Sm C8 89.56(8) 1_545 7 ? O2W Sm C8 153.58(9) . 7 ? O6 Sm C8 94.99(8) 5_655 7 ? O5 Sm C8 97.47(8) . 7 ? O2 Sm C8 131.48(8) . 7 ? O4 Sm C8 25.10(8) 7 7 ? O1 Sm C8 79.07(8) . 7 ? O3 Sm C8 25.70(7) 7 7 ? C1 Sm C8 105.34(9) . 7 ? O2 C1 O1 120.2(3) . . ? O2 C1 C2 119.7(3) . . ? O1 C1 C2 120.0(3) . . ? O2 C1 Sm 59.62(17) . . ? O1 C1 Sm 60.63(16) . . ? C2 C1 Sm 177.1(2) . . ? C3 C2 C7 119.4(3) . . ? C3 C2 C1 119.3(3) . . ? C7 C2 C1 121.3(3) . . ? C2 C3 C4 120.6(3) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 120.9(3) . . ? C7 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? C6 C7 C2 119.1(3) . . ? C6 C7 C8 115.9(3) . . ? C2 C7 C8 124.9(3) . . ? O4 C8 O3 120.3(3) . . ? O4 C8 C7 119.9(3) . . ? O3 C8 C7 119.6(3) . . ? O4 C8 Sm 57.68(16) . 7 ? O3 C8 Sm 62.64(15) . 7 ? C7 C8 Sm 172.2(2) . 7 ? O6 C9 O5 126.3(3) . . ? O6 C9 C9 117.1(3) . 5_655 ? O5 C9 C9 116.6(4) . 5_655 ? Sm O1W H1WB 126.7 . . ? Sm O1W H1WA 118.1 . . ? H1WB O1W H1WA 107.9 . . ? C1 O1 Sm 93.10(19) . . ? Sm O2W H2WA 119.7 . . ? Sm O2W H2WB 123.6 . . ? H2WA O2W H2WB 115.1 . . ? C1 O2 Sm 94.2(2) . . ? C8 O3 Sm 152.11(19) . 1_565 ? C8 O3 Sm 91.66(17) . 7 ? Sm O3 Sm 116.11(9) 1_565 7 ? C8 O4 Sm 97.22(19) . 7 ? C9 O5 Sm 119.2(2) . . ? C9 O6 Sm 121.0(2) . 5_655 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.564 _refine_diff_density_min -0.720 _refine_diff_density_rms 0.098 # Attachment '3.cif' data_a _database_code_depnum_ccdc_archive 'CCDC 725102' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Eu O9' _chemical_formula_weight 427.15 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' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.673(2) _cell_length_b 5.9691(12) _cell_length_c 18.456(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.65(3) _cell_angle_gamma 90.00 _cell_volume 1274.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11096 _cell_measurement_theta_min 3.52 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 4.963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3371 _exptl_absorpt_correction_T_max 0.4164 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11096 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0610 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2885 _reflns_number_gt 2517 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0000P)^2^+3.6539P] 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 2885 _refine_ls_number_parameters 186 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0568 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.0904 _refine_ls_wR_factor_gt 0.0884 _refine_ls_goodness_of_fit_ref 1.361 _refine_ls_restrained_S_all 1.361 _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 Eu Eu 0.84709(2) 0.91280(4) 0.040451(15) 0.01619(11) Uani 1 1 d . . . C1 C 0.9674(5) 0.6226(9) 0.1450(3) 0.0203(13) Uani 1 1 d . . . C2 C 1.0280(6) 0.4689(10) 0.2014(3) 0.0208(13) Uani 1 1 d . . . C3 C 1.0241(7) 0.5114(11) 0.2754(4) 0.0299(16) Uani 1 1 d . . . H8A H 0.9850 0.6372 0.2889 0.036 Uiso 1 1 calc R . . C4 C 1.0772(7) 0.3698(12) 0.3291(4) 0.0387(18) Uani 1 1 d . . . H9A H 1.0753 0.4020 0.3782 0.046 Uiso 1 1 calc R . . C5 C 1.1335(7) 0.1794(12) 0.3089(4) 0.0360(17) Uani 1 1 d . . . H10A H 1.1675 0.0813 0.3446 0.054 Uiso 1 1 calc R . . C6 C 1.1391(6) 0.1351(11) 0.2359(4) 0.0298(15) Uani 1 1 d . . . H5A H 1.1774 0.0078 0.2228 0.036 Uiso 1 1 calc R . . C7 C 1.0880(5) 0.2796(10) 0.1820(3) 0.0199(12) Uani 1 1 d . . . C8 C 1.1033(5) 0.2208(9) 0.1043(3) 0.0184(12) Uiso 1 1 d . . . C9 C 0.6262(5) 0.7073(10) 0.0208(4) 0.0249(14) Uani 1 1 d . . . C10 C 0.5104(6) 0.6070(11) -0.0019(5) 0.0349(17) Uani 1 1 d . . . H2A H 0.445(7) 0.716(14) -0.027(4) 0.05(2) Uiso 1 1 d . . . O1 O 0.9852(4) 0.6072(7) 0.0788(2) 0.0225(9) Uani 1 1 d . . . O1W O 0.8104(4) 1.2495(8) -0.0301(3) 0.0282(10) Uani 1 1 d D . . H1WB H 0.873(3) 1.282(11) -0.041(4) 0.023(19) Uiso 1 1 d D . . H1WA H 0.784(8) 1.331(13) -0.002(4) 0.07(3) Uiso 1 1 d D . . O2W O 0.7823(6) 1.1794(9) 0.1242(4) 0.0365(13) Uani 1 1 d . . . H7B H 0.792(8) 1.177(14) 0.164(5) 0.05(3) Uiso 1 1 d . . . H7A H 0.743(9) 1.266(17) 0.109(5) 0.06(3) Uiso 1 1 d . . . O2 O 0.8980(4) 0.7661(7) 0.1637(2) 0.0291(10) Uani 1 1 d . . . O3W O 0.7988(6) 0.1157(10) 0.2710(3) 0.0598(17) Uani 1 1 d . . . O3 O 1.0284(4) 0.1001(7) 0.0657(2) 0.0218(9) Uiso 1 1 d . . . O4 O 1.1927(4) 0.2806(7) 0.0796(2) 0.0257(10) Uiso 1 1 d . . . O5 O 0.6382(4) 0.9140(7) 0.0096(3) 0.0328(11) Uani 1 1 d . . . O6 O 0.7107(4) 0.5894(7) 0.0497(3) 0.0281(10) 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 Eu 0.01522(16) 0.01440(17) 0.01921(17) 0.00017(11) 0.00331(11) -0.00126(12) C1 0.022(3) 0.019(3) 0.021(3) 0.001(2) 0.005(2) 0.000(2) C2 0.022(3) 0.021(3) 0.019(3) 0.002(2) 0.002(2) -0.001(2) C3 0.038(5) 0.030(4) 0.021(3) -0.004(3) 0.004(3) 0.005(3) C4 0.045(5) 0.047(5) 0.023(4) 0.001(3) 0.004(3) 0.003(4) C5 0.043(5) 0.039(4) 0.024(4) 0.008(3) -0.005(3) 0.004(3) C6 0.033(4) 0.026(3) 0.030(4) 0.002(3) -0.002(3) 0.007(3) C7 0.019(3) 0.022(3) 0.018(3) -0.002(2) 0.001(2) -0.002(2) C9 0.016(3) 0.023(3) 0.037(4) -0.005(3) 0.007(3) -0.002(2) C10 0.016(3) 0.029(3) 0.058(5) -0.002(3) 0.000(3) -0.006(3) O1 0.027(2) 0.023(2) 0.019(2) 0.0025(17) 0.0055(18) 0.0023(18) O1W 0.028(3) 0.026(2) 0.032(3) 0.006(2) 0.006(2) 0.003(2) O2W 0.047(4) 0.033(3) 0.030(3) -0.004(2) 0.008(3) 0.014(3) O2 0.035(3) 0.028(2) 0.026(2) 0.0007(19) 0.0091(19) 0.012(2) O3W 0.073(5) 0.065(4) 0.046(4) -0.002(3) 0.025(3) 0.002(3) O5 0.020(2) 0.018(2) 0.061(3) 0.001(2) 0.006(2) -0.0006(19) O6 0.021(2) 0.023(2) 0.040(3) 0.0066(19) 0.002(2) -0.0026(19) _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 Eu O3 2.384(4) 1_565 ? Eu O1W 2.402(5) . ? Eu O2W 2.409(5) . ? Eu O5 2.429(5) . ? Eu O2 2.437(4) . ? Eu O1 2.475(4) . ? Eu O4 2.487(4) 3_765 ? Eu O6 2.522(4) . ? Eu O3 2.591(4) 3_765 ? Eu C1 2.823(6) . ? Eu C9 2.835(6) . ? Eu C8 2.919(6) 3_765 ? Eu H1WB 2.71(6) . ? Eu H1WA 2.69(9) . ? Eu H7A 2.82(10) . ? C1 O2 1.259(7) . ? C1 O1 1.269(7) . ? C1 C2 1.494(8) . ? C2 C3 1.396(9) . ? C2 C7 1.400(8) . ? C3 C4 1.384(10) . ? C3 H8A 0.9300 . ? C4 C5 1.388(10) . ? C4 H9A 0.9300 . ? C5 C6 1.383(10) . ? C5 H10A 0.9300 . ? C6 C7 1.390(8) . ? C6 H5A 0.9300 . ? C7 C8 1.509(8) . ? C8 O4 1.246(7) . ? C8 O3 1.275(7) . ? C8 Eu 2.919(6) 3_765 ? C9 O5 1.262(7) . ? C9 O6 1.270(7) . ? C9 C10 1.487(9) . ? C10 C10 1.304(13) 3_665 ? C10 H2A 1.06(8) . ? O1W H1WB 0.80(2) . ? O1W H1WA 0.80(2) . ? O2W H7B 0.73(9) . ? O2W H7A 0.72(10) . ? O3 Eu 2.384(4) 1_545 ? O3 Eu 2.591(4) 3_765 ? O4 Eu 2.487(4) 3_765 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Eu O1W 78.65(16) 1_565 . ? O3 Eu O2W 84.93(18) 1_565 . ? O1W Eu O2W 75.3(2) . . ? O3 Eu O5 151.86(14) 1_565 . ? O1W Eu O5 76.67(16) . . ? O2W Eu O5 75.9(2) . . ? O3 Eu O2 83.48(15) 1_565 . ? O1W Eu O2 144.14(16) . . ? O2W Eu O2 72.35(19) . . ? O5 Eu O2 109.40(17) . . ? O3 Eu O1 76.24(14) 1_565 . ? O1W Eu O1 146.55(16) . . ? O2W Eu O1 123.5(2) . . ? O5 Eu O1 131.66(14) . . ? O2 Eu O1 53.09(14) . . ? O3 Eu O4 116.57(15) 1_565 3_765 ? O1W Eu O4 84.67(15) . 3_765 ? O2W Eu O4 147.23(19) . 3_765 ? O5 Eu O4 74.34(16) . 3_765 ? O2 Eu O4 131.19(15) . 3_765 ? O1 Eu O4 87.13(14) . 3_765 ? O3 Eu O6 153.84(14) 1_565 . ? O1W Eu O6 127.47(16) . . ? O2W Eu O6 101.94(19) . . ? O5 Eu O6 52.78(14) . . ? O2 Eu O6 74.89(16) . . ? O1 Eu O6 79.03(14) . . ? O4 Eu O6 70.15(15) 3_765 . ? O3 Eu O3 65.71(16) 1_565 3_765 ? O1W Eu O3 72.12(15) . 3_765 ? O2W Eu O3 139.49(17) . 3_765 ? O5 Eu O3 118.02(16) . 3_765 ? O2 Eu O3 127.13(14) . 3_765 ? O1 Eu O3 77.56(13) . 3_765 ? O4 Eu O3 50.93(14) 3_765 3_765 ? O6 Eu O3 116.83(14) . 3_765 ? O3 Eu C1 78.84(16) 1_565 . ? O1W Eu C1 156.96(17) . . ? O2W Eu C1 97.9(2) . . ? O5 Eu C1 123.66(17) . . ? O2 Eu C1 26.40(15) . . ? O1 Eu C1 26.68(16) . . ? O4 Eu C1 109.92(16) 3_765 . ? O6 Eu C1 75.24(16) . . ? O3 Eu C1 102.72(15) 3_765 . ? O3 Eu C9 175.30(16) 1_565 . ? O1W Eu C9 101.48(18) . . ? O2W Eu C9 90.6(2) . . ? O5 Eu C9 26.31(16) . . ? O2 Eu C9 93.93(18) . . ? O1 Eu C9 105.34(16) . . ? O4 Eu C9 68.06(17) 3_765 . ? O6 Eu C9 26.61(16) . . ? O3 Eu C9 118.87(16) 3_765 . ? C1 Eu C9 100.55(18) . . ? O3 Eu C8 91.58(16) 1_565 3_765 ? O1W Eu C8 77.03(16) . 3_765 ? O2W Eu C8 152.3(2) . 3_765 ? O5 Eu C8 95.84(17) . 3_765 ? O2 Eu C8 134.67(15) . 3_765 ? O1 Eu C8 81.91(15) . 3_765 ? O4 Eu C8 25.04(15) 3_765 3_765 ? O6 Eu C8 93.27(16) . 3_765 ? O3 Eu C8 25.89(14) 3_765 3_765 ? C1 Eu C8 108.44(17) . 3_765 ? C9 Eu C8 93.03(17) . 3_765 ? O3 Eu H1WB 64.3(11) 1_565 . ? O1W Eu H1WB 16.8(8) . . ? O2W Eu H1WB 83.4(13) . . ? O5 Eu H1WB 92.8(9) . . ? O2 Eu H1WB 141.2(14) . . ? O1 Eu H1WB 130.1(9) . . ? O4 Eu H1WB 84.6(15) 3_765 . ? O6 Eu H1WB 141.1(11) . . ? O3 Eu H1WB 59.4(12) 3_765 . ? C1 Eu H1WB 142.9(10) . . ? C9 Eu H1WB 116.6(10) . . ? C8 Eu H1WB 70.4(14) 3_765 . ? O3 Eu H1WA 80(2) 1_565 . ? O1W Eu H1WA 16.9(11) . . ? O2W Eu H1WA 58.5(11) . . ? O5 Eu H1WA 73(2) . . ? O2 Eu H1WA 129.0(13) . . ? O1 Eu H1WA 155(2) . . ? O4 Eu H1WA 99.2(15) 3_765 . ? O6 Eu H1WA 125(2) . . ? O3 Eu H1WA 88.0(12) 3_765 . ? C1 Eu H1WA 149.4(18) . . ? C9 Eu H1WA 99(2) . . ? C8 Eu H1WA 93.8(11) 3_765 . ? H1WB Eu H1WA 29.3(17) . . ? O3 Eu H7A 89(2) 1_565 . ? O1W Eu H7A 64(2) . . ? O2W Eu H7A 13.0(19) . . ? O5 Eu H7A 68(2) . . ? O2 Eu H7A 85(2) . . ? O1 Eu H7A 137(2) . . ? O4 Eu H7A 135(2) 3_765 . ? O6 Eu H7A 103(2) . . ? O3 Eu H7A 133(2) 3_765 . ? C1 Eu H7A 111(2) . . ? C9 Eu H7A 87(2) . . ? C8 Eu H7A 140(2) 3_765 . ? H1WB Eu H7A 74(3) . . ? H1WA Eu H7A 47(2) . . ? O2 C1 O1 120.6(5) . . ? O2 C1 C2 119.2(5) . . ? O1 C1 C2 120.2(5) . . ? O2 C1 Eu 59.4(3) . . ? O1 C1 Eu 61.2(3) . . ? C2 C1 Eu 178.3(4) . . ? C3 C2 C7 118.7(6) . . ? C3 C2 C1 119.7(6) . . ? C7 C2 C1 121.6(5) . . ? C4 C3 C2 121.2(7) . . ? C4 C3 H8A 119.4 . . ? C2 C3 H8A 119.4 . . ? C3 C4 C5 119.4(7) . . ? C3 C4 H9A 120.3 . . ? C5 C4 H9A 120.3 . . ? C6 C5 C4 120.2(6) . . ? C6 C5 H10A 119.9 . . ? C4 C5 H10A 119.9 . . ? C5 C6 C7 120.5(6) . . ? C5 C6 H5A 119.8 . . ? C7 C6 H5A 119.8 . . ? C6 C7 C2 119.9(6) . . ? C6 C7 C8 116.2(5) . . ? C2 C7 C8 123.8(5) . . ? O4 C8 O3 120.2(5) . . ? O4 C8 C7 119.5(5) . . ? O3 C8 C7 120.2(5) . . ? O4 C8 Eu 57.7(3) . 3_765 ? O3 C8 Eu 62.5(3) . 3_765 ? C7 C8 Eu 174.7(4) . 3_765 ? O5 C9 O6 120.9(6) . . ? O5 C9 C10 117.7(6) . . ? O6 C9 C10 121.4(6) . . ? O5 C9 Eu 58.6(3) . . ? O6 C9 Eu 62.8(3) . . ? C10 C9 Eu 171.0(5) . . ? C10 C10 C9 123.2(9) 3_665 . ? C10 C10 H2A 120(4) 3_665 . ? C9 C10 H2A 117(4) . . ? C1 O1 Eu 92.2(4) . . ? Eu O1W H1WB 104(5) . . ? Eu O1W H1WA 102(7) . . ? H1WB O1W H1WA 117(9) . . ? Eu O2W H7B 128(7) . . ? Eu O2W H7A 118(8) . . ? H7B O2W H7A 114(10) . . ? C1 O2 Eu 94.2(4) . . ? C8 O3 Eu 154.0(4) . 1_545 ? C8 O3 Eu 91.6(3) . 3_765 ? Eu O3 Eu 114.29(16) 1_545 3_765 ? C8 O4 Eu 97.3(4) . 3_765 ? C9 O5 Eu 95.1(4) . . ? C9 O6 Eu 90.5(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.397 _refine_diff_density_min -1.203 _refine_diff_density_rms 0.178 # Attachment '4.cif' data_wz-339-2 _database_code_depnum_ccdc_archive 'CCDC 725103' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 O9 Sm' _chemical_formula_weight 425.54 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' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.703(2) _cell_length_b 5.9725(12) _cell_length_c 18.446(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.62(3) _cell_angle_gamma 90.00 _cell_volume 1278.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 11718 _cell_measurement_theta_min 3.51 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour clorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 4.637 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4697 _exptl_absorpt_correction_T_max 0.6857 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11718 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2922 _reflns_number_gt 2440 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0000P)^2^+24.2889P] 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 2922 _refine_ls_number_parameters 182 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1131 _refine_ls_wR_factor_gt 0.1086 _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_restrained_S_all 1.216 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sm1 Sm 0.84715(3) 0.91266(7) 0.04062(2) 0.01355(13) Uani 1 1 d . . . C1 C 0.9683(7) 0.6200(13) 0.1457(4) 0.0159(16) Uani 1 1 d . . . C2 C 1.0275(7) 0.4661(14) 0.2023(5) 0.0202(17) Uani 1 1 d . . . C3 C 1.0230(9) 0.5053(17) 0.2759(5) 0.029(2) Uani 1 1 d . . . H3C H 0.9820 0.6285 0.2894 0.034 Uiso 1 1 calc R . . C4 C 1.0768(10) 0.3686(18) 0.3295(5) 0.037(3) Uani 1 1 d . . . H4A H 1.0749 0.4017 0.3786 0.044 Uiso 1 1 calc R . . C5 C 1.1342(9) 0.1800(18) 0.3095(5) 0.035(2) Uani 1 1 d . . . H5A H 1.1694 0.0843 0.3455 0.042 Uiso 1 1 calc R . . C6 C 1.1396(9) 0.1324(17) 0.2367(5) 0.030(2) Uani 1 1 d . . . H6A H 1.1769 0.0039 0.2238 0.036 Uiso 1 1 calc R . . C7 C 1.0885(7) 0.2787(14) 0.1823(4) 0.0179(17) Uani 1 1 d . . . C8 C 1.1031(6) 0.2235(13) 0.1055(4) 0.0134(15) Uiso 1 1 d . . . C9 C 0.6249(7) 0.7089(15) 0.0209(5) 0.0209(18) Uani 1 1 d . . . C10 C 0.5107(9) 0.6105(15) -0.0032(6) 0.027(2) Uani 1 1 d . . . H10 H 0.453(9) 0.686(18) -0.028(6) 0.03(3) Uiso 1 1 d . . . O1W O 0.7837(6) 1.1798(13) 0.1251(4) 0.0344(17) Uani 1 1 d D . . H1WB H 0.724(4) 1.220(12) 0.1429(16) 0.052 Uiso 1 1 d D . . H1WA H 0.7763 1.1585 0.1695 0.052 Uiso 1 1 calc RD . . O1 O 0.9861(5) 0.6057(10) 0.0796(3) 0.0188(12) Uani 1 1 d . . . O2W O 0.8114(6) 1.2502(11) -0.0292(4) 0.0256(14) Uani 1 1 d D . . H2WB H 0.791(5) 1.376(5) -0.040(3) 0.038 Uiso 1 1 d D . . H2WA H 0.8415 1.3180 -0.0601 0.038 Uiso 1 1 calc RD . . O2 O 0.8991(6) 0.7633(11) 0.1645(3) 0.0272(14) Uani 1 1 d . . . O3W O 0.7012(9) 0.6122(19) 0.2296(5) 0.060(3) Uani 1 1 d D . . H3WB H 0.737(13) 0.71(2) 0.207(8) 0.089 Uiso 1 1 d D . . H3WA H 0.638(8) 0.66(3) 0.206(8) 0.089 Uiso 1 1 d D . . O3 O 1.1925(5) 0.2820(10) 0.0804(3) 0.0223(13) Uiso 1 1 d . . . O4 O 1.0291(5) 0.0996(10) 0.0659(3) 0.0195(12) Uiso 1 1 d . . . O5 O 0.7100(5) 0.5889(11) 0.0500(3) 0.0244(13) Uani 1 1 d . . . O6 O 0.6379(5) 0.9117(11) 0.0098(4) 0.0275(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sm1 0.01123(19) 0.0120(2) 0.0174(2) 0.00006(17) 0.00178(13) -0.00112(16) C1 0.014(4) 0.013(4) 0.020(4) 0.003(3) 0.002(3) -0.003(3) C2 0.019(4) 0.019(4) 0.021(4) 0.003(3) 0.000(3) -0.001(3) C3 0.036(5) 0.031(5) 0.017(4) 0.000(4) -0.001(4) 0.010(4) C4 0.056(7) 0.037(6) 0.015(4) -0.003(4) -0.005(4) 0.007(5) C5 0.044(6) 0.035(6) 0.022(5) 0.006(4) -0.006(4) 0.011(5) C6 0.038(5) 0.028(5) 0.022(4) 0.002(4) -0.002(4) 0.011(4) C7 0.018(4) 0.017(4) 0.018(4) 0.002(3) -0.004(3) -0.003(3) C9 0.015(4) 0.018(4) 0.030(5) -0.003(4) 0.005(3) 0.000(3) C10 0.027(5) 0.014(4) 0.039(5) -0.003(4) 0.003(4) -0.003(4) O1W 0.044(4) 0.032(4) 0.028(4) -0.006(3) 0.009(3) 0.011(3) O1 0.020(3) 0.017(3) 0.019(3) 0.003(2) 0.003(2) 0.000(2) O2W 0.028(3) 0.017(3) 0.032(3) 0.008(3) 0.005(3) 0.000(3) O2 0.033(4) 0.027(3) 0.022(3) 0.003(3) 0.006(3) 0.012(3) O3W 0.069(7) 0.073(7) 0.041(5) 0.011(5) 0.022(5) -0.006(6) O5 0.017(3) 0.019(3) 0.036(3) 0.003(3) 0.000(3) -0.006(3) O6 0.014(3) 0.014(3) 0.054(4) 0.001(3) 0.003(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sm1 O4 2.395(6) 1_565 ? Sm1 O2W 2.399(6) . ? Sm1 O1W 2.415(7) . ? Sm1 O6 2.440(6) . ? Sm1 O2 2.453(6) . ? Sm1 O1 2.492(6) . ? Sm1 O3 2.505(6) 3_765 ? Sm1 O5 2.534(6) . ? Sm1 O4 2.593(6) 3_765 ? Sm1 C1 2.845(8) . ? Sm1 C9 2.851(8) . ? Sm1 C8 2.946(8) 3_765 ? C1 O2 1.258(10) . ? C1 O1 1.267(10) . ? C1 C2 1.490(11) . ? C2 C3 1.387(12) . ? C2 C7 1.403(12) . ? C3 C4 1.370(13) . ? C3 H3C 0.9300 . ? C4 C5 1.386(15) . ? C4 H4A 0.9300 . ? C5 C6 1.382(13) . ? C5 H5A 0.9300 . ? C6 C7 1.403(12) . ? C6 H6A 0.9300 . ? C7 C8 1.486(11) . ? C8 O3 1.249(10) . ? C8 O4 1.289(9) . ? C8 Sm1 2.946(8) 3_765 ? C9 O6 1.241(11) . ? C9 O5 1.285(10) . ? C9 C10 1.474(12) . ? C10 C10 1.352(18) 3_665 ? C10 H10 0.89(10) . ? O1W H1WB 0.85(2) . ? O2W H2WB 0.81(2) . ? O3W H3WB 0.85(2) . ? O3W H3WA 0.85(2) . ? O3 Sm1 2.505(6) 3_765 ? O4 Sm1 2.395(6) 1_545 ? O4 Sm1 2.593(6) 3_765 ? 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 O4 Sm1 O2W 78.5(2) 1_565 . ? O4 Sm1 O1W 84.7(2) 1_565 . ? O2W Sm1 O1W 75.2(2) . . ? O4 Sm1 O6 152.3(2) 1_565 . ? O2W Sm1 O6 77.2(2) . . ? O1W Sm1 O6 76.5(2) . . ? O4 Sm1 O2 83.3(2) 1_565 . ? O2W Sm1 O2 144.1(2) . . ? O1W Sm1 O2 72.5(2) . . ? O6 Sm1 O2 109.5(2) . . ? O4 Sm1 O1 76.0(2) 1_565 . ? O2W Sm1 O1 146.5(2) . . ? O1W Sm1 O1 123.0(2) . . ? O6 Sm1 O1 131.4(2) . . ? O2 Sm1 O1 52.56(19) . . ? O4 Sm1 O3 116.43(19) 1_565 3_765 ? O2W Sm1 O3 85.0(2) . 3_765 ? O1W Sm1 O3 147.7(2) . 3_765 ? O6 Sm1 O3 74.3(2) . 3_765 ? O2 Sm1 O3 130.9(2) . 3_765 ? O1 Sm1 O3 87.29(19) . 3_765 ? O4 Sm1 O5 153.8(2) 1_565 . ? O2W Sm1 O5 127.7(2) . . ? O1W Sm1 O5 102.0(2) . . ? O6 Sm1 O5 52.3(2) . . ? O2 Sm1 O5 74.9(2) . . ? O1 Sm1 O5 79.28(19) . . ? O3 Sm1 O5 70.3(2) 3_765 . ? O4 Sm1 O4 65.8(2) 1_565 3_765 ? O2W Sm1 O4 72.1(2) . 3_765 ? O1W Sm1 O4 139.3(2) . 3_765 ? O6 Sm1 O4 117.9(2) . 3_765 ? O2 Sm1 O4 127.0(2) . 3_765 ? O1 Sm1 O4 77.83(18) . 3_765 ? O3 Sm1 O4 50.77(19) 3_765 3_765 ? O5 Sm1 O4 116.9(2) . 3_765 ? O4 Sm1 C1 78.7(2) 1_565 . ? O2W Sm1 C1 156.6(2) . . ? O1W Sm1 C1 97.7(2) . . ? O6 Sm1 C1 123.5(2) . . ? O2 Sm1 C1 26.1(2) . . ? O1 Sm1 C1 26.4(2) . . ? O3 Sm1 C1 109.8(2) 3_765 . ? O5 Sm1 C1 75.4(2) . . ? O4 Sm1 C1 102.8(2) 3_765 . ? O4 Sm1 C9 175.2(2) 1_565 . ? O2W Sm1 C9 101.5(2) . . ? O1W Sm1 C9 90.6(3) . . ? O6 Sm1 C9 25.7(2) . . ? O2 Sm1 C9 94.2(2) . . ? O1 Sm1 C9 105.8(2) . . ? O3 Sm1 C9 68.3(2) 3_765 . ? O5 Sm1 C9 26.8(2) . . ? O4 Sm1 C9 118.9(2) 3_765 . ? C1 Sm1 C9 100.9(2) . . ? O4 Sm1 C8 91.6(2) 1_565 3_765 ? O2W Sm1 C8 77.4(2) . 3_765 ? O1W Sm1 C8 152.6(2) . 3_765 ? O6 Sm1 C8 95.7(2) . 3_765 ? O2 Sm1 C8 134.2(2) . 3_765 ? O1 Sm1 C8 82.0(2) . 3_765 ? O3 Sm1 C8 24.8(2) 3_765 3_765 ? O5 Sm1 C8 93.2(2) . 3_765 ? O4 Sm1 C8 25.92(19) 3_765 3_765 ? C1 Sm1 C8 108.2(2) . 3_765 ? C9 Sm1 C8 93.1(2) . 3_765 ? O2 C1 O1 120.3(7) . . ? O2 C1 C2 118.9(7) . . ? O1 C1 C2 120.8(7) . . ? O2 C1 Sm1 59.3(4) . . ? O1 C1 Sm1 61.1(4) . . ? C2 C1 Sm1 177.7(6) . . ? C3 C2 C7 118.7(8) . . ? C3 C2 C1 120.4(8) . . ? C7 C2 C1 120.9(8) . . ? C4 C3 C2 122.2(9) . . ? C4 C3 H3C 118.9 . . ? C2 C3 H3C 118.9 . . ? C3 C4 C5 119.0(9) . . ? C3 C4 H4A 120.5 . . ? C5 C4 H4A 120.5 . . ? C6 C5 C4 120.8(9) . . ? C6 C5 H5A 119.6 . . ? C4 C5 H5A 119.6 . . ? C5 C6 C7 119.8(9) . . ? C5 C6 H6A 120.1 . . ? C7 C6 H6A 120.1 . . ? C2 C7 C6 119.5(8) . . ? C2 C7 C8 123.7(7) . . ? C6 C7 C8 116.9(8) . . ? O3 C8 O4 118.9(7) . . ? O3 C8 C7 119.9(7) . . ? O4 C8 C7 120.9(7) . . ? O3 C8 Sm1 57.4(4) . 3_765 ? O4 C8 Sm1 61.5(4) . 3_765 ? C7 C8 Sm1 174.2(5) . 3_765 ? O6 C9 O5 120.6(8) . . ? O6 C9 C10 117.7(8) . . ? O5 C9 C10 121.7(8) . . ? O6 C9 Sm1 58.3(4) . . ? O5 C9 Sm1 62.7(4) . . ? C10 C9 Sm1 169.8(7) . . ? C10 C10 C9 122.3(12) 3_665 . ? C10 C10 H10 114(7) 3_665 . ? C9 C10 H10 123(7) . . ? Sm1 O1W H1WB 141(5) . . ? C1 O1 Sm1 92.5(5) . . ? Sm1 O2W H2WB 160(3) . . ? C1 O2 Sm1 94.6(5) . . ? H3WB O3W H3WA 89(10) . . ? C8 O3 Sm1 97.7(5) . 3_765 ? C8 O4 Sm1 153.0(5) . 1_545 ? C8 O4 Sm1 92.5(4) . 3_765 ? Sm1 O4 Sm1 114.2(2) 1_545 3_765 ? C9 O5 Sm1 90.5(5) . . ? C9 O6 Sm1 96.0(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.306 _refine_diff_density_min -1.310 _refine_diff_density_rms 0.240 # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 725104' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H23 O21 Pr3' _chemical_formula_weight 1118.19 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.542(2) _cell_length_b 13.199(3) _cell_length_c 13.687(3) _cell_angle_alpha 115.50(3) _cell_angle_beta 91.29(3) _cell_angle_gamma 115.05(3) _cell_volume 1650.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16241 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 4.450 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4821 _exptl_absorpt_correction_T_max 0.6955 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16241 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 7460 _reflns_number_gt 6478 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0000P)^2^+7.7969P] 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 7460 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0383 _refine_ls_R_factor_gt 0.0303 _refine_ls_wR_factor_ref 0.0657 _refine_ls_wR_factor_gt 0.0629 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pr1 Pr 0.64622(2) 0.14788(2) 0.47707(2) 0.01242(6) Uani 1 1 d . . . Pr2 Pr 1.00014(2) 0.14928(2) 0.39867(2) 0.01444(6) Uani 1 1 d . . . Pr3 Pr 0.45345(2) 0.33002(2) 0.51112(2) 0.01335(6) Uani 1 1 d . . . C1 C 0.4640(5) 0.0822(4) 0.2795(4) 0.0159(9) Uani 1 1 d . . . C2 C 0.3707(5) 0.0293(5) 0.1713(4) 0.0188(10) Uani 1 1 d . . . C3 C 0.3857(6) -0.0560(5) 0.0753(5) 0.0317(13) Uani 1 1 d . . . H3A H 0.4537 -0.0752 0.0805 0.038 Uiso 1 1 calc R . . C4 C 0.3008(7) -0.1133(6) -0.0285(5) 0.0401(15) Uani 1 1 d . . . H4A H 0.3157 -0.1663 -0.0924 0.048 Uiso 1 1 calc R . . C5 C 0.1953(6) -0.0924(6) -0.0375(5) 0.0361(14) Uani 1 1 d . . . H5A H 0.1369 -0.1329 -0.1066 0.043 Uiso 1 1 calc R . . C6 C 0.1776(5) -0.0099(5) 0.0581(4) 0.0280(12) Uani 1 1 d . . . H6A H 0.1054 0.0035 0.0525 0.034 Uiso 1 1 calc R . . C7 C 0.2634(5) 0.0529(4) 0.1612(4) 0.0193(10) Uani 1 1 d . . . C8 C 0.2427(5) 0.1494(5) 0.2566(4) 0.0187(10) Uani 1 1 d . . . C9 C 0.9594(4) -0.1546(4) 0.3461(4) 0.0165(9) Uani 1 1 d . . . C10 C 0.9867(5) -0.2123(4) 0.2358(4) 0.0188(10) Uani 1 1 d . . . C11 C 1.0824(5) -0.2526(5) 0.2230(4) 0.0209(10) Uani 1 1 d . . . C12 C 1.0969(6) -0.3173(6) 0.1168(5) 0.0333(13) Uani 1 1 d . . . H12A H 1.1602 -0.3444 0.1081 0.050 Uiso 1 1 calc R . . C13 C 1.0169(7) -0.3413(6) 0.0238(5) 0.0383(15) Uani 1 1 d . . . H13A H 1.0265 -0.3849 -0.0472 0.046 Uiso 1 1 calc R . . C14 C 0.9229(6) -0.3006(6) 0.0360(5) 0.0364(14) Uani 1 1 d . . . H14A H 0.8687 -0.3175 -0.0264 0.044 Uiso 1 1 calc R . . C15 C 0.9103(6) -0.2343(5) 0.1424(5) 0.0288(12) Uani 1 1 d . . . H15A H 0.8495 -0.2042 0.1509 0.035 Uiso 1 1 calc R . . C16 C 1.1748(5) -0.2188(5) 0.3231(4) 0.0204(10) Uiso 1 1 d . . . C17 C 0.2689(5) 0.0423(4) 0.7420(4) 0.0175(9) Uiso 1 1 d . . . C18 C 0.5043(4) 0.1828(4) 0.6656(4) 0.0143(9) Uani 1 1 d . . . C19 C 0.4919(5) 0.2308(4) 0.7843(4) 0.0168(9) Uani 1 1 d . . . C20 C 0.3903(5) 0.1641(4) 0.8208(4) 0.0180(10) Uani 1 1 d . . . C21 C 0.3934(6) 0.2152(5) 0.9340(4) 0.0278(12) Uani 1 1 d . . . H21A H 0.312(6) 0.165(5) 0.968(5) 0.033 Uiso 1 1 d . . . C22 C 0.4974(7) 0.3331(6) 1.0113(5) 0.0504(19) Uani 1 1 d . . . H22A H 0.5007 0.3666 1.0872 0.076 Uiso 1 1 calc R . . C23 C 0.5964(7) 0.4000(6) 0.9735(6) 0.054(2) Uani 1 1 d . . . H23A H 0.6660 0.4796 1.0246 0.065 Uiso 1 1 calc R . . C24 C 0.5936(6) 0.3506(5) 0.8615(5) 0.0301(12) Uani 1 1 d . . . H24A H 0.6600 0.3976 0.8375 0.036 Uiso 1 1 calc R . . C25 C 0.8909(5) 0.3152(4) 0.3884(4) 0.0183(10) Uani 1 1 d . . . C26 C 0.8247(5) 0.3905(5) 0.3836(5) 0.0242(11) Uani 1 1 d . . . H26A H 0.7554 0.3382 0.3149 0.029 Uiso 1 1 calc R . . H26B H 0.8892 0.4652 0.3808 0.029 Uiso 1 1 calc R . . C27 C 0.7643(5) 0.4348(5) 0.4823(4) 0.0200(10) Uiso 1 1 d . . . H27A H 0.8334 0.4800 0.5512 0.024 Uiso 1 1 calc R . . C28 C 0.7246(5) 0.5307(4) 0.4796(4) 0.0153(9) Uiso 1 1 d . . . O1 O 0.4274(3) 0.1130(3) 0.3703(3) 0.0159(7) Uani 1 1 d . . . O1W O 0.2253(4) 0.1281(3) 0.4720(3) 0.0208(8) Uani 1 1 d . . . H1WB H 0.232(6) 0.068(6) 0.447(5) 0.025 Uiso 1 1 d . . . H1WA H 0.214(6) 0.124(5) 0.527(5) 0.025 Uiso 1 1 d . . . O2 O 0.5749(3) 0.0902(3) 0.2769(3) 0.0209(7) Uani 1 1 d . . . O2W O 0.3430(4) 0.3699(4) 0.6801(3) 0.0366(10) Uani 1 1 d . . . H2WA H 0.2625 0.3257 0.6566 0.055 Uiso 1 1 calc R . . H2WB H 0.4111 0.4254 0.7231 0.044 Uiso 1 1 d R . . O3W O 0.6111(4) 0.5269(3) 0.6944(3) 0.0306(9) Uani 1 1 d . . . H3WA H 0.6226 0.5918 0.6928 0.037 Uiso 1 1 calc R . . H3WB H 0.6794 0.5239 0.7056 0.046 Uiso 1 1 d R . . O3 O 0.3405(3) 0.2562(3) 0.3233(3) 0.0205(7) Uani 1 1 d . . . O4W O 0.8536(4) 0.5556(4) 0.7635(4) 0.0335(10) Uani 1 1 d . . . H4WB H 0.864(7) 0.501(7) 0.739(6) 0.050 Uiso 1 1 d . . . H4WA H 0.928(7) 0.611(7) 0.751(6) 0.050 Uiso 1 1 d . . . O4 O 0.1250(4) 0.1207(4) 0.2638(3) 0.0295(8) Uiso 1 1 d . . . O5 O 0.9525(4) -0.2075(3) 0.4060(3) 0.0238(8) Uani 1 1 d . . . O6 O 0.9348(4) -0.0632(3) 0.3740(3) 0.0244(8) Uani 1 1 d . . . O7 O 1.2206(3) -0.1091(3) 0.4073(3) 0.0224(7) Uiso 1 1 d . . . O8 O 1.2084(3) -0.2990(3) 0.3220(3) 0.0234(7) Uiso 1 1 d . . . O9 O 0.2594(3) -0.0082(3) 0.6374(3) 0.0196(7) Uiso 1 1 d . . . O10 O 0.1740(4) -0.0035(3) 0.7800(3) 0.0256(8) Uiso 1 1 d . . . O11 O 0.5142(4) 0.2489(3) 0.6203(3) 0.0232(8) Uani 1 1 d . . . O12 O 0.5164(3) 0.0832(3) 0.6165(3) 0.0178(7) Uiso 1 1 d . . . O13 O 0.8690(3) 0.2705(3) 0.4566(3) 0.0215(7) Uani 1 1 d . . . O14 O 0.9643(3) 0.2944(3) 0.3256(3) 0.0217(7) Uani 1 1 d . . . O15 O 0.6591(3) 0.3356(3) 0.4862(3) 0.0172(7) Uiso 1 1 d . . . O16 O 0.6031(3) 0.4966(3) 0.4619(3) 0.0177(7) Uiso 1 1 d . . . O17 O 0.8109(3) 0.6378(3) 0.4973(3) 0.0215(7) Uiso 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 Pr1 0.01116(12) 0.01086(12) 0.01714(13) 0.00776(10) 0.00374(10) 0.00588(9) Pr2 0.01102(12) 0.01214(12) 0.02004(14) 0.00805(10) 0.00283(10) 0.00526(10) Pr3 0.01168(12) 0.01173(12) 0.01857(14) 0.00839(10) 0.00345(10) 0.00617(10) C1 0.018(2) 0.012(2) 0.017(2) 0.0071(19) 0.0032(19) 0.0065(18) C2 0.020(2) 0.023(2) 0.016(2) 0.010(2) 0.005(2) 0.011(2) C3 0.037(3) 0.035(3) 0.022(3) 0.008(2) 0.005(2) 0.022(3) C4 0.049(4) 0.046(4) 0.022(3) 0.009(3) 0.009(3) 0.028(3) C5 0.033(3) 0.039(3) 0.018(3) 0.004(2) -0.003(2) 0.013(3) C6 0.024(3) 0.026(3) 0.023(3) 0.007(2) -0.002(2) 0.009(2) C7 0.016(2) 0.017(2) 0.020(3) 0.008(2) 0.003(2) 0.0057(19) C8 0.017(2) 0.026(3) 0.018(2) 0.013(2) 0.005(2) 0.012(2) C9 0.009(2) 0.014(2) 0.020(2) 0.0060(19) -0.0005(18) 0.0016(17) C10 0.021(2) 0.017(2) 0.021(3) 0.011(2) 0.004(2) 0.009(2) C11 0.021(3) 0.020(2) 0.020(3) 0.007(2) 0.006(2) 0.012(2) C12 0.035(3) 0.045(4) 0.028(3) 0.015(3) 0.010(3) 0.028(3) C13 0.054(4) 0.046(4) 0.019(3) 0.012(3) 0.010(3) 0.032(3) C14 0.045(4) 0.041(3) 0.022(3) 0.011(3) 0.000(3) 0.025(3) C15 0.034(3) 0.034(3) 0.026(3) 0.015(2) 0.005(2) 0.023(3) C18 0.010(2) 0.012(2) 0.019(2) 0.0068(19) 0.0004(18) 0.0047(17) C19 0.017(2) 0.013(2) 0.021(3) 0.0084(19) 0.0036(19) 0.0070(19) C20 0.016(2) 0.017(2) 0.019(3) 0.008(2) 0.0040(19) 0.0077(19) C21 0.027(3) 0.029(3) 0.018(3) 0.009(2) 0.005(2) 0.008(2) C22 0.047(4) 0.047(4) 0.019(3) -0.001(3) 0.011(3) 0.007(3) C23 0.043(4) 0.035(4) 0.033(4) -0.001(3) 0.008(3) -0.006(3) C24 0.028(3) 0.023(3) 0.024(3) 0.006(2) 0.008(2) 0.006(2) C25 0.013(2) 0.016(2) 0.026(3) 0.011(2) 0.005(2) 0.0055(19) C26 0.032(3) 0.026(3) 0.031(3) 0.020(2) 0.017(2) 0.019(2) O1 0.0156(16) 0.0153(16) 0.0138(17) 0.0042(13) 0.0040(13) 0.0078(13) O1W 0.0254(19) 0.0139(17) 0.026(2) 0.0111(16) 0.0133(16) 0.0101(15) O2 0.0173(17) 0.0303(19) 0.0220(19) 0.0156(16) 0.0074(15) 0.0142(15) O2W 0.023(2) 0.044(2) 0.035(2) 0.018(2) 0.0094(18) 0.0110(18) O3W 0.038(2) 0.0170(18) 0.033(2) 0.0104(17) -0.0014(18) 0.0115(17) O3 0.0258(19) 0.0159(17) 0.0216(19) 0.0105(15) 0.0010(15) 0.0101(15) O4W 0.036(2) 0.027(2) 0.030(2) 0.0099(19) 0.0063(19) 0.0132(19) O5 0.031(2) 0.0237(19) 0.025(2) 0.0151(16) 0.0096(16) 0.0169(16) O6 0.030(2) 0.0178(18) 0.026(2) 0.0066(15) 0.0015(16) 0.0158(16) O11 0.029(2) 0.0233(18) 0.030(2) 0.0208(16) 0.0091(16) 0.0153(16) O13 0.0170(17) 0.0245(18) 0.034(2) 0.0203(17) 0.0122(16) 0.0124(15) O14 0.0223(18) 0.0224(18) 0.027(2) 0.0139(16) 0.0123(15) 0.0137(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pr1 O15 2.366(3) . ? Pr1 O12 2.479(4) 2_656 ? Pr1 O13 2.491(3) . ? Pr1 O9 2.516(3) 2_656 ? Pr1 O2 2.517(3) . ? Pr1 O7 2.527(3) 2_756 ? Pr1 O8 2.568(4) 2_756 ? Pr1 O1 2.645(3) . ? Pr1 O12 2.658(3) . ? Pr1 O11 2.747(4) . ? Pr1 C16 2.920(5) 2_756 ? Pr1 C1 2.944(5) . ? Pr2 O4 2.368(4) 1_655 ? Pr2 O5 2.417(4) 2_756 ? Pr2 O17 2.430(4) 2_766 ? Pr2 O6 2.436(3) . ? Pr2 O10 2.485(4) 2_656 ? Pr2 O13 2.549(3) . ? Pr2 O9 2.665(4) 2_656 ? Pr2 O14 2.673(3) . ? Pr2 O1W 2.930(4) 1_655 ? Pr2 C17 2.938(5) 2_656 ? Pr2 C25 3.000(4) . ? Pr3 O15 2.380(3) . ? Pr3 O11 2.416(3) . ? Pr3 O3 2.424(4) . ? Pr3 O16 2.520(3) 2_666 ? Pr3 O16 2.526(3) . ? Pr3 O1 2.549(3) . ? Pr3 O3W 2.556(4) . ? Pr3 O2W 2.628(4) . ? Pr3 O1W 2.662(4) . ? C1 O2 1.241(5) . ? C1 O1 1.274(6) . ? C1 C2 1.497(7) . ? C2 C3 1.388(7) . ? C2 C7 1.417(6) . ? C3 C4 1.392(8) . ? C3 H3A 0.9300 . ? C4 C5 1.371(8) . ? C4 H4A 0.9300 . ? C5 C6 1.384(8) . ? C5 H5A 0.9300 . ? C6 C7 1.376(7) . ? C6 H6A 0.9300 . ? C7 C8 1.491(7) . ? C8 O3 1.262(6) . ? C8 O4 1.265(6) . ? C9 O6 1.256(5) . ? C9 O5 1.272(6) . ? C9 C10 1.481(7) . ? C10 C15 1.382(7) . ? C10 C11 1.400(6) . ? C11 C12 1.390(7) . ? C11 C16 1.489(7) . ? C12 C13 1.388(8) . ? C12 H12A 0.9300 . ? C13 C14 1.385(8) . ? C13 H13A 0.9300 . ? C14 C15 1.388(8) . ? C14 H14A 0.9300 . ? C15 H15A 0.9300 . ? C16 O7 1.262(6) . ? C16 O8 1.266(6) . ? C16 Pr1 2.920(5) 2_756 ? C17 O10 1.254(6) . ? C17 O9 1.271(6) . ? C17 C20 1.497(7) . ? C17 Pr2 2.938(5) 2_656 ? C18 O11 1.243(5) . ? C18 O12 1.263(5) . ? C18 C19 1.504(7) . ? C19 C24 1.388(7) . ? C19 C20 1.389(6) . ? C20 C21 1.390(7) . ? C21 C22 1.388(8) . ? C21 H21A 1.14(6) . ? C22 C23 1.385(9) . ? C22 H22A 0.9300 . ? C23 C24 1.376(8) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 O14 1.248(6) . ? C25 O13 1.281(6) . ? C25 C26 1.508(6) . ? C26 C27 1.536(7) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 O15 1.382(6) . ? C27 C28 1.532(6) . ? C27 H27A 0.9800 . ? C28 O17 1.245(6) . ? C28 O16 1.258(5) . ? O1W Pr2 2.930(4) 1_455 ? O1W H1WB 0.76(6) . ? O1W H1WA 0.79(6) . ? O2W H2WA 0.8200 . ? O2W H2WB 0.7884 . ? O3W H3WA 0.8200 . ? O3W H3WB 0.8201 . ? O4W H4WB 0.72(7) . ? O4W H4WA 0.94(7) . ? O4 Pr2 2.368(4) 1_455 ? O5 Pr2 2.417(4) 2_756 ? O7 Pr1 2.527(3) 2_756 ? O8 Pr1 2.568(4) 2_756 ? O9 Pr1 2.516(3) 2_656 ? O9 Pr2 2.665(4) 2_656 ? O10 Pr2 2.485(4) 2_656 ? O12 Pr1 2.479(4) 2_656 ? O16 Pr3 2.520(3) 2_666 ? O17 Pr2 2.430(4) 2_766 ? 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 O15 Pr1 O12 137.10(11) . 2_656 ? O15 Pr1 O13 72.58(11) . . ? O12 Pr1 O13 132.97(11) 2_656 . ? O15 Pr1 O9 130.38(11) . 2_656 ? O12 Pr1 O9 67.19(11) 2_656 2_656 ? O13 Pr1 O9 66.67(11) . 2_656 ? O15 Pr1 O2 75.06(12) . . ? O12 Pr1 O2 75.62(12) 2_656 . ? O13 Pr1 O2 82.83(12) . . ? O9 Pr1 O2 72.95(11) 2_656 . ? O15 Pr1 O7 133.19(12) . 2_756 ? O12 Pr1 O7 88.77(11) 2_656 2_756 ? O13 Pr1 O7 81.43(11) . 2_756 ? O9 Pr1 O7 66.83(11) 2_656 2_756 ? O2 Pr1 O7 139.78(11) . 2_756 ? O15 Pr1 O8 84.39(11) . 2_756 ? O12 Pr1 O8 130.40(11) 2_656 2_756 ? O13 Pr1 O8 75.27(12) . 2_756 ? O9 Pr1 O8 110.35(11) 2_656 2_756 ? O2 Pr1 O8 153.63(11) . 2_756 ? O7 Pr1 O8 51.14(11) 2_756 2_756 ? O15 Pr1 O1 65.69(11) . . ? O12 Pr1 O1 71.51(11) 2_656 . ? O13 Pr1 O1 122.76(11) . . ? O9 Pr1 O1 115.82(11) 2_656 . ? O2 Pr1 O1 50.30(10) . . ? O7 Pr1 O1 155.38(11) 2_756 . ? O8 Pr1 O1 133.83(10) 2_756 . ? O15 Pr1 O12 113.06(10) . . ? O12 Pr1 O12 68.36(12) 2_656 . ? O13 Pr1 O12 144.11(11) . . ? O9 Pr1 O12 116.53(10) 2_656 . ? O2 Pr1 O12 133.03(11) . . ? O7 Pr1 O12 69.31(10) 2_756 . ? O8 Pr1 O12 70.33(11) 2_756 . ? O1 Pr1 O12 89.30(10) . . ? O15 Pr1 O11 65.72(10) . . ? O12 Pr1 O11 100.81(11) 2_656 . ? O13 Pr1 O11 126.21(11) . . ? O9 Pr1 O11 163.89(10) 2_656 . ? O2 Pr1 O11 115.70(10) . . ? O7 Pr1 O11 103.43(11) 2_756 . ? O8 Pr1 O11 68.46(11) 2_756 . ? O1 Pr1 O11 67.41(10) . . ? O12 Pr1 O11 47.44(9) . . ? O15 Pr1 C16 108.91(13) . 2_756 ? O12 Pr1 C16 110.54(13) 2_656 2_756 ? O13 Pr1 C16 76.59(13) . 2_756 ? O9 Pr1 C16 88.23(12) 2_656 2_756 ? O2 Pr1 C16 156.41(12) . 2_756 ? O7 Pr1 C16 25.50(12) 2_756 2_756 ? O8 Pr1 C16 25.65(12) 2_756 2_756 ? O1 Pr1 C16 153.05(12) . 2_756 ? O12 Pr1 C16 68.01(12) . 2_756 ? O11 Pr1 C16 86.12(12) . 2_756 ? O15 Pr1 C1 69.78(12) . . ? O12 Pr1 C1 70.43(12) 2_656 . ? O13 Pr1 C1 103.76(13) . . ? O9 Pr1 C1 93.39(12) 2_656 . ? O2 Pr1 C1 24.73(11) . . ? O7 Pr1 C1 156.03(12) 2_756 . ? O8 Pr1 C1 152.79(11) 2_756 . ? O1 Pr1 C1 25.65(11) . . ? O12 Pr1 C1 111.45(12) . . ? O11 Pr1 C1 92.40(12) . . ? C16 Pr1 C1 178.35(13) 2_756 . ? O4 Pr2 O5 132.09(13) 1_655 2_756 ? O4 Pr2 O17 84.05(13) 1_655 2_766 ? O5 Pr2 O17 70.68(12) 2_756 2_766 ? O4 Pr2 O6 91.17(13) 1_655 . ? O5 Pr2 O6 82.06(12) 2_756 . ? O17 Pr2 O6 137.33(12) 2_766 . ? O4 Pr2 O10 77.58(13) 1_655 2_656 ? O5 Pr2 O10 143.68(12) 2_756 2_656 ? O17 Pr2 O10 142.35(12) 2_766 2_656 ? O6 Pr2 O10 76.17(12) . 2_656 ? O4 Pr2 O13 133.53(12) 1_655 . ? O5 Pr2 O13 84.21(12) 2_756 . ? O17 Pr2 O13 83.34(11) 2_766 . ? O6 Pr2 O13 126.70(11) . . ? O10 Pr2 O13 85.95(12) 2_656 . ? O4 Pr2 O9 126.06(12) 1_655 2_656 ? O5 Pr2 O9 94.35(12) 2_756 2_656 ? O17 Pr2 O9 145.29(11) 2_766 2_656 ? O6 Pr2 O9 66.41(11) . 2_656 ? O10 Pr2 O9 50.32(11) 2_656 2_656 ? O13 Pr2 O9 63.66(11) . 2_656 ? O4 Pr2 O14 83.95(11) 1_655 . ? O5 Pr2 O14 123.57(11) 2_756 . ? O17 Pr2 O14 73.19(11) 2_766 . ? O6 Pr2 O14 148.53(12) . . ? O10 Pr2 O14 72.42(11) 2_656 . ? O13 Pr2 O14 49.58(10) . . ? O9 Pr2 O14 91.57(10) 2_656 . ? O4 Pr2 O1W 67.99(12) 1_655 1_655 ? O5 Pr2 O1W 65.56(11) 2_756 1_655 ? O17 Pr2 O1W 71.15(11) 2_766 1_655 ? O6 Pr2 O1W 67.83(11) . 1_655 ? O10 Pr2 O1W 128.55(11) 2_656 1_655 ? O13 Pr2 O1W 145.26(11) . 1_655 ? O9 Pr2 O1W 132.00(10) 2_656 1_655 ? O14 Pr2 O1W 136.24(10) . 1_655 ? O4 Pr2 C17 100.85(14) 1_655 2_656 ? O5 Pr2 C17 118.90(13) 2_756 2_656 ? O17 Pr2 C17 155.86(12) 2_766 2_656 ? O6 Pr2 C17 66.61(13) . 2_656 ? O10 Pr2 C17 24.99(12) 2_656 2_656 ? O13 Pr2 C17 76.17(12) . 2_656 ? O9 Pr2 C17 25.63(12) 2_656 2_656 ? O14 Pr2 C17 83.76(12) . 2_656 ? O1W Pr2 C17 132.70(11) 1_655 2_656 ? O4 Pr2 C25 108.49(13) 1_655 . ? O5 Pr2 C25 104.98(12) 2_756 . ? O17 Pr2 C25 77.66(12) 2_766 . ? O6 Pr2 C25 142.61(12) . . ? O10 Pr2 C25 77.49(13) 2_656 . ? O13 Pr2 C25 25.04(12) . . ? O9 Pr2 C25 76.38(11) 2_656 . ? O14 Pr2 C25 24.56(11) . . ? O1W Pr2 C25 148.80(12) 1_655 . ? C17 Pr2 C25 78.38(13) 2_656 . ? O15 Pr3 O11 71.21(12) . . ? O15 Pr3 O3 102.05(12) . . ? O11 Pr3 O3 140.03(11) . . ? O15 Pr3 O16 125.56(11) . 2_666 ? O11 Pr3 O16 139.34(11) . 2_666 ? O3 Pr3 O16 77.45(11) . 2_666 ? O15 Pr3 O16 64.15(10) . . ? O11 Pr3 O16 128.40(11) . . ? O3 Pr3 O16 75.85(12) . . ? O16 Pr3 O16 63.13(12) 2_666 . ? O15 Pr3 O1 67.10(11) . . ? O11 Pr3 O1 74.11(11) . . ? O3 Pr3 O1 67.36(11) . . ? O16 Pr3 O1 144.70(11) 2_666 . ? O16 Pr3 O1 108.83(11) . . ? O15 Pr3 O3W 78.94(12) . . ? O11 Pr3 O3W 74.24(12) . . ? O3 Pr3 O3W 144.75(11) . . ? O16 Pr3 O3W 73.96(11) 2_666 . ? O16 Pr3 O3W 73.07(12) . . ? O1 Pr3 O3W 139.33(11) . . ? O15 Pr3 O2W 134.64(12) . . ? O11 Pr3 O2W 71.68(12) . . ? O3 Pr3 O2W 123.17(12) . . ? O16 Pr3 O2W 72.81(12) 2_666 . ? O16 Pr3 O2W 126.49(12) . . ? O1 Pr3 O2W 124.68(12) . . ? O3W Pr3 O2W 66.58(13) . . ? O15 Pr3 O1W 127.61(11) . . ? O11 Pr3 O1W 77.68(12) . . ? O3 Pr3 O1W 76.53(12) . . ? O16 Pr3 O1W 105.56(11) 2_666 . ? O16 Pr3 O1W 151.89(11) . . ? O1 Pr3 O1W 64.36(11) . . ? O3W Pr3 O1W 130.95(13) . . ? O2W Pr3 O1W 66.76(13) . . ? O15 Pr3 Pr1 36.36(8) . . ? O11 Pr3 Pr1 45.81(8) . . ? O3 Pr3 Pr1 105.75(8) . . ? O16 Pr3 Pr1 161.77(8) 2_666 . ? O16 Pr3 Pr1 99.81(7) . . ? O1 Pr3 Pr1 43.72(8) . . ? O3W Pr3 Pr1 95.62(9) . . ? O2W Pr3 Pr1 117.35(9) . . ? O1W Pr3 Pr1 92.58(8) . . ? O2 C1 O1 121.7(4) . . ? O2 C1 C2 118.0(4) . . ? O1 C1 C2 120.2(4) . . ? O2 C1 Pr1 58.0(2) . . ? O1 C1 Pr1 64.0(2) . . ? C2 C1 Pr1 171.2(3) . . ? C3 C2 C7 118.1(5) . . ? C3 C2 C1 117.0(4) . . ? C7 C2 C1 124.7(4) . . ? C2 C3 C4 121.1(5) . . ? C2 C3 H3A 119.5 . . ? C4 C3 H3A 119.5 . . ? C5 C4 C3 120.6(5) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 118.7(5) . . ? C4 C5 H5A 120.6 . . ? C6 C5 H5A 120.6 . . ? C7 C6 C5 122.0(5) . . ? C7 C6 H6A 119.0 . . ? C5 C6 H6A 119.0 . . ? C6 C7 C2 119.4(5) . . ? C6 C7 C8 117.6(4) . . ? C2 C7 C8 122.9(4) . . ? O3 C8 O4 123.0(4) . . ? O3 C8 C7 119.6(4) . . ? O4 C8 C7 117.3(4) . . ? O6 C9 O5 122.3(5) . . ? O6 C9 C10 120.4(4) . . ? O5 C9 C10 117.1(4) . . ? C15 C10 C11 119.3(5) . . ? C15 C10 C9 119.2(4) . . ? C11 C10 C9 121.4(4) . . ? C12 C11 C10 119.9(5) . . ? C12 C11 C16 119.7(4) . . ? C10 C11 C16 120.3(4) . . ? C13 C12 C11 120.0(5) . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C14 C13 C12 120.4(5) . . ? C14 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? C13 C14 C15 119.4(5) . . ? C13 C14 H14A 120.3 . . ? C15 C14 H14A 120.3 . . ? C10 C15 C14 121.1(5) . . ? C10 C15 H15A 119.5 . . ? C14 C15 H15A 119.5 . . ? O7 C16 O8 120.9(5) . . ? O7 C16 C11 119.1(4) . . ? O8 C16 C11 119.9(4) . . ? O7 C16 Pr1 59.5(3) . 2_756 ? O8 C16 Pr1 61.4(3) . 2_756 ? C11 C16 Pr1 178.5(3) . 2_756 ? O10 C17 O9 120.8(4) . . ? O10 C17 C20 119.0(4) . . ? O9 C17 C20 120.0(4) . . ? O10 C17 Pr2 56.8(3) . 2_656 ? O9 C17 Pr2 65.1(3) . 2_656 ? C20 C17 Pr2 164.3(3) . 2_656 ? O11 C18 O12 120.4(4) . . ? O11 C18 C19 118.7(4) . . ? O12 C18 C19 120.6(4) . . ? C24 C19 C20 119.2(5) . . ? C24 C19 C18 115.5(4) . . ? C20 C19 C18 125.3(4) . . ? C19 C20 C21 120.1(5) . . ? C19 C20 C17 122.7(4) . . ? C21 C20 C17 117.0(4) . . ? C22 C21 C20 120.4(5) . . ? C22 C21 H21A 117(3) . . ? C20 C21 H21A 123(3) . . ? C23 C22 C21 118.9(6) . . ? C23 C22 H22A 120.6 . . ? C21 C22 H22A 120.6 . . ? C24 C23 C22 121.0(6) . . ? C24 C23 H23A 119.5 . . ? C22 C23 H23A 119.5 . . ? C23 C24 C19 120.2(5) . . ? C23 C24 H24A 119.9 . . ? C19 C24 H24A 119.9 . . ? O14 C25 O13 120.2(4) . . ? O14 C25 C26 120.7(4) . . ? O13 C25 C26 119.1(4) . . ? O14 C25 Pr2 62.9(2) . . ? O13 C25 Pr2 57.4(2) . . ? C26 C25 Pr2 175.0(3) . . ? C25 C26 C27 114.7(4) . . ? C25 C26 H26A 108.6 . . ? C27 C26 H26A 108.6 . . ? C25 C26 H26B 108.6 . . ? C27 C26 H26B 108.6 . . ? H26A C26 H26B 107.6 . . ? O15 C27 C28 110.9(4) . . ? O15 C27 C26 113.7(4) . . ? C28 C27 C26 109.4(4) . . ? O15 C27 H27A 107.5 . . ? C28 C27 H27A 107.5 . . ? C26 C27 H27A 107.5 . . ? O17 C28 O16 123.1(4) . . ? O17 C28 C27 120.1(4) . . ? O16 C28 C27 116.7(4) . . ? C1 O1 Pr3 128.8(3) . . ? C1 O1 Pr1 90.4(3) . . ? Pr3 O1 Pr1 94.53(11) . . ? Pr3 O1W Pr2 111.30(12) . 1_455 ? Pr3 O1W H1WB 110(4) . . ? Pr2 O1W H1WB 126(5) 1_455 . ? Pr3 O1W H1WA 112(4) . . ? Pr2 O1W H1WA 104(4) 1_455 . ? H1WB O1W H1WA 92(6) . . ? C1 O2 Pr1 97.2(3) . . ? Pr3 O2W H2WA 109.5 . . ? Pr3 O2W H2WB 92.1 . . ? H2WA O2W H2WB 157.6 . . ? Pr3 O3W H3WA 109.5 . . ? Pr3 O3W H3WB 109.4 . . ? H3WA O3W H3WB 114.0 . . ? C8 O3 Pr3 128.6(3) . . ? H4WB O4W H4WA 97(7) . . ? C8 O4 Pr2 141.0(3) . 1_455 ? C9 O5 Pr2 139.2(3) . 2_756 ? C9 O6 Pr2 148.5(3) . . ? C16 O7 Pr1 95.0(3) . 2_756 ? C16 O8 Pr1 92.9(3) . 2_756 ? C17 O9 Pr1 129.2(3) . 2_656 ? C17 O9 Pr2 89.3(3) . 2_656 ? Pr1 O9 Pr2 109.88(12) 2_656 2_656 ? C17 O10 Pr2 98.2(3) . 2_656 ? C18 O11 Pr3 160.5(3) . . ? C18 O11 Pr1 92.3(3) . . ? Pr3 O11 Pr1 95.09(12) . . ? C18 O12 Pr1 132.4(3) . 2_656 ? C18 O12 Pr1 96.0(3) . . ? Pr1 O12 Pr1 111.64(12) 2_656 . ? C25 O13 Pr1 124.9(3) . . ? C25 O13 Pr2 97.6(3) . . ? Pr1 O13 Pr2 114.60(12) . . ? C25 O14 Pr2 92.6(3) . . ? C27 O15 Pr1 128.7(3) . . ? C27 O15 Pr3 124.2(3) . . ? Pr1 O15 Pr3 107.02(13) . . ? C28 O16 Pr3 115.1(3) . 2_666 ? C28 O16 Pr3 118.7(3) . . ? Pr3 O16 Pr3 116.87(12) 2_666 . ? C28 O17 Pr2 157.5(3) . 2_766 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.354 _refine_diff_density_min -0.811 _refine_diff_density_rms 0.167 # Attachment '6.cif' data_wz-320-3a _database_code_depnum_ccdc_archive 'CCDC 725105' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 Eu O8' _chemical_formula_weight 424.17 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' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.362(3) _cell_length_b 5.9634(13) _cell_length_c 15.641(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.626(3) _cell_angle_gamma 90.00 _cell_volume 1243.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5920 _cell_measurement_theta_min 1.94 _cell_measurement_theta_max 25 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.265 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 820 _exptl_absorpt_coefficient_mu 5.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4933 _exptl_absorpt_correction_T_max 0.6150 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5920 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2187 _reflns_number_gt 1679 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0268P)^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 2187 _refine_ls_number_parameters 178 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0639 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.971 _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 Eu1 Eu 0.86942(3) 0.08015(6) 0.41937(2) 0.01618(12) Uani 1 1 d . . . C1 C 0.9873(5) 0.3605(11) 0.3226(4) 0.0198(17) Uani 1 1 d . . . C2 C 1.0499(5) 0.5101(11) 0.2713(4) 0.0155(16) Uani 1 1 d . . . C3 C 1.0640(6) 0.4612(13) 0.1866(4) 0.0274(19) Uani 1 1 d . . . H6A H 1.0324 0.3364 0.1616 0.033 Uiso 1 1 calc R . . C4 C 1.1239(6) 0.5933(14) 0.1382(4) 0.0316(19) Uani 1 1 d . . . H5C H 1.1335 0.5559 0.0815 0.038 Uiso 1 1 calc R . . C5 C 1.1688(5) 0.7791(13) 0.1741(4) 0.0278(18) Uani 1 1 d . . . H4A H 1.2089 0.8693 0.1419 0.033 Uiso 1 1 calc R . . C6 C 1.1549(5) 0.8340(12) 0.2594(4) 0.0232(17) Uani 1 1 d . . . H3A H 1.1847 0.9623 0.2833 0.035 Uiso 1 1 calc R . . C7 C 1.0969(5) 0.6989(11) 0.3088(4) 0.0189(16) Uani 1 1 d . . . C8 C 1.0949(5) 0.7607(12) 0.4015(4) 0.0168(15) Uiso 1 1 d . . . C9 C 0.6818(5) 0.2995(12) 0.4022(4) 0.0195(17) Uani 1 1 d . . . C10 C 0.5938(5) 0.4521(13) 0.4121(4) 0.0277(18) Uani 1 1 d . . . H10A H 0.5458 0.4304 0.3636 0.033 Uiso 1 1 calc R . . H10B H 0.6168 0.6063 0.4106 0.033 Uiso 1 1 calc R . . C11 C 0.5411(5) 0.4150(12) 0.4942(4) 0.0248(17) Uani 1 1 d . . . H11A H 0.5124 0.2655 0.4934 0.037 Uiso 1 1 calc R . . H11B H 0.5900 0.4239 0.5427 0.037 Uiso 1 1 calc R . . O1 O 0.9334(4) 0.2119(8) 0.2852(3) 0.0287(13) Uani 1 1 d . . . O1W O 0.8073(4) -0.1963(9) 0.3158(3) 0.0345(14) Uani 1 1 d D . . H1WA H 0.780(6) -0.327(7) 0.332(5) 0.052 Uiso 1 1 d D . . H1WB H 0.797(6) -0.166(13) 0.2610(17) 0.052 Uiso 1 1 d D . . O2 O 0.9887(3) 0.3843(7) 0.4035(3) 0.0196(11) Uani 1 1 d . . . O2W O 0.8391(4) -0.2436(9) 0.5042(3) 0.0302(12) Uani 1 1 d D . . H8A H 0.872(5) -0.318(11) 0.546(3) 0.045 Uiso 1 1 d D . . H8B H 0.797(5) -0.356(9) 0.495(5) 0.045 Uiso 1 1 d D . . O3 O 1.0268(3) 0.8882(8) 0.4278(3) 0.0239(12) Uiso 1 1 d . . . O4 O 1.1664(3) 0.7034(8) 0.4520(3) 0.0249(12) Uiso 1 1 d . . . O5 O 0.7569(4) 0.3789(8) 0.3642(3) 0.0305(13) Uani 1 1 d . . . O6 O 0.6849(4) 0.1055(8) 0.4300(3) 0.0293(12) 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 Eu1 0.0186(2) 0.01398(19) 0.01602(19) -0.00014(17) 0.00119(13) 0.00082(18) C1 0.019(4) 0.012(4) 0.028(4) 0.003(3) 0.001(3) 0.006(3) C2 0.013(4) 0.021(4) 0.013(4) 0.003(3) 0.002(3) -0.003(3) C3 0.037(5) 0.027(5) 0.019(4) -0.005(3) 0.004(3) -0.002(4) C4 0.035(5) 0.042(5) 0.017(4) 0.002(4) -0.005(3) 0.004(5) C5 0.028(4) 0.031(5) 0.025(4) 0.008(4) 0.006(3) 0.001(4) C6 0.026(4) 0.019(4) 0.023(4) -0.001(3) -0.005(3) -0.008(3) C7 0.020(4) 0.021(4) 0.016(4) -0.001(3) 0.003(3) 0.006(3) C9 0.019(4) 0.028(5) 0.010(4) -0.004(3) -0.007(3) 0.002(3) C10 0.026(4) 0.028(5) 0.029(4) 0.007(4) 0.000(3) 0.009(4) C11 0.020(4) 0.027(4) 0.028(4) 0.000(4) 0.004(3) 0.005(4) O1 0.037(3) 0.031(3) 0.018(3) -0.008(2) 0.002(2) -0.012(3) O1W 0.061(4) 0.024(3) 0.018(3) -0.002(3) 0.001(3) -0.014(3) O2 0.029(3) 0.018(3) 0.013(3) -0.004(2) 0.004(2) -0.004(2) O2W 0.035(3) 0.015(3) 0.040(3) 0.012(3) -0.006(2) -0.004(3) O5 0.023(3) 0.033(3) 0.036(3) 0.015(3) 0.008(2) 0.011(3) O6 0.028(3) 0.019(3) 0.041(3) 0.002(3) 0.006(2) 0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O3 2.391(5) 1_545 ? Eu1 O2W 2.391(5) . ? Eu1 O1W 2.421(5) . ? Eu1 O2 2.438(4) . ? Eu1 O1 2.445(5) . ? Eu1 O5 2.453(4) . ? Eu1 O4 2.463(5) 3_766 ? Eu1 O6 2.487(5) . ? Eu1 O3 2.693(4) 3_766 ? Eu1 C1 2.805(7) . ? Eu1 C9 2.826(7) . ? Eu1 C8 2.967(6) 3_766 ? C1 O1 1.263(8) . ? C1 O2 1.271(7) . ? C1 C2 1.491(9) . ? C2 C3 1.381(9) . ? C2 C7 1.399(9) . ? C3 C4 1.383(10) . ? C3 H6A 0.9300 . ? C4 C5 1.364(10) . ? C4 H5C 0.9300 . ? C5 C6 1.397(9) . ? C5 H4A 0.9300 . ? C6 C7 1.386(9) . ? C6 H3A 0.9300 . ? C7 C8 1.499(8) . ? C8 O4 1.248(7) . ? C8 O3 1.273(7) . ? C8 Eu1 2.967(6) 3_766 ? C9 O6 1.236(8) . ? C9 O5 1.288(8) . ? C9 C10 1.502(9) . ? C10 C11 1.520(9) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C11 1.515(12) 3_666 ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? O1W H1WA 0.90(2) . ? O1W H1WB 0.88(2) . ? O2W H8A 0.89(2) . ? O2W H8B 0.89(2) . ? O3 Eu1 2.391(5) 1_565 ? O3 Eu1 2.693(4) 3_766 ? O4 Eu1 2.462(5) 3_766 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Eu1 O2W 76.24(17) 1_545 . ? O3 Eu1 O1W 88.52(18) 1_545 . ? O2W Eu1 O1W 76.01(17) . . ? O3 Eu1 O2 77.47(15) 1_545 . ? O2W Eu1 O2 142.37(15) . . ? O1W Eu1 O2 129.60(16) . . ? O3 Eu1 O1 81.21(16) 1_545 . ? O2W Eu1 O1 144.70(18) . . ? O1W Eu1 O1 76.61(16) . . ? O2 Eu1 O1 53.64(14) . . ? O3 Eu1 O5 152.24(16) 1_545 . ? O2W Eu1 O5 131.28(17) . . ? O1W Eu1 O5 94.75(18) . . ? O2 Eu1 O5 79.29(16) . . ? O1 Eu1 O5 72.83(16) . . ? O3 Eu1 O4 114.93(15) 1_545 3_766 ? O2W Eu1 O4 85.51(17) . 3_766 ? O1W Eu1 O4 145.84(17) . 3_766 ? O2 Eu1 O4 81.67(15) . 3_766 ? O1 Eu1 O4 128.99(16) . 3_766 ? O5 Eu1 O4 76.10(16) . 3_766 ? O3 Eu1 O6 153.91(16) 1_545 . ? O2W Eu1 O6 78.96(17) . . ? O1W Eu1 O6 77.68(18) . . ? O2 Eu1 O6 128.26(15) . . ? O1 Eu1 O6 116.10(16) . . ? O5 Eu1 O6 52.46(16) . . ? O4 Eu1 O6 70.66(15) 3_766 . ? O3 Eu1 O3 65.34(17) 1_545 3_766 ? O2W Eu1 O3 70.11(15) . 3_766 ? O1W Eu1 O3 140.98(16) . 3_766 ? O2 Eu1 O3 74.64(14) . 3_766 ? O1 Eu1 O3 123.44(14) . 3_766 ? O5 Eu1 O3 122.07(15) . 3_766 ? O4 Eu1 O3 49.75(14) 3_766 3_766 ? O6 Eu1 O3 113.15(15) . 3_766 ? O3 Eu1 C1 78.05(17) 1_545 . ? O2W Eu1 C1 154.29(19) . . ? O1W Eu1 C1 103.04(19) . . ? O2 Eu1 C1 26.92(16) . . ? O1 Eu1 C1 26.72(16) . . ? O5 Eu1 C1 74.35(17) . . ? O4 Eu1 C1 105.83(18) 3_766 . ? O6 Eu1 C1 126.38(17) . . ? O3 Eu1 C1 99.32(17) 3_766 . ? O3 Eu1 C9 177.53(16) 1_545 . ? O2W Eu1 C9 104.2(2) . . ? O1W Eu1 C9 89.26(19) . . ? O2 Eu1 C9 103.17(19) . . ? O1 Eu1 C9 97.23(18) . . ? O5 Eu1 C9 27.07(17) . . ? O4 Eu1 C9 67.54(16) 3_766 . ? O6 Eu1 C9 25.91(17) . . ? O3 Eu1 C9 117.12(16) 3_766 . ? C1 Eu1 C9 101.4(2) . . ? O3 Eu1 C8 90.72(17) 1_545 3_766 ? O2W Eu1 C8 75.96(18) . 3_766 ? O1W Eu1 C8 151.30(18) . 3_766 ? O2 Eu1 C8 77.94(16) . 3_766 ? O1 Eu1 C8 131.55(17) . 3_766 ? O5 Eu1 C8 99.09(17) . 3_766 ? O4 Eu1 C8 24.38(16) 3_766 3_766 ? O6 Eu1 C8 91.05(16) . 3_766 ? O3 Eu1 C8 25.40(14) 3_766 3_766 ? C1 Eu1 C8 104.85(19) . 3_766 ? C9 Eu1 C8 91.75(18) . 3_766 ? O1 C1 O2 120.8(6) . . ? O1 C1 C2 119.6(6) . . ? O2 C1 C2 119.6(6) . . ? O1 C1 Eu1 60.5(4) . . ? O2 C1 Eu1 60.2(3) . . ? C2 C1 Eu1 179.8(6) . . ? C3 C2 C7 119.1(6) . . ? C3 C2 C1 120.3(6) . . ? C7 C2 C1 120.6(6) . . ? C2 C3 C4 121.6(7) . . ? C2 C3 H6A 119.2 . . ? C4 C3 H6A 119.2 . . ? C5 C4 C3 119.4(7) . . ? C5 C4 H5C 120.3 . . ? C3 C4 H5C 120.3 . . ? C4 C5 C6 120.1(7) . . ? C4 C5 H4A 119.9 . . ? C6 C5 H4A 119.9 . . ? C7 C6 C5 120.6(7) . . ? C7 C6 H3A 119.7 . . ? C5 C6 H3A 119.7 . . ? C6 C7 C2 119.1(6) . . ? C6 C7 C8 116.2(6) . . ? C2 C7 C8 124.6(6) . . ? O4 C8 O3 119.6(6) . . ? O4 C8 C7 119.0(6) . . ? O3 C8 C7 121.1(5) . . ? O4 C8 Eu1 54.5(3) . 3_766 ? O3 C8 Eu1 65.2(3) . 3_766 ? C7 C8 Eu1 168.7(4) . 3_766 ? O6 C9 O5 119.8(6) . . ? O6 C9 C10 122.7(7) . . ? O5 C9 C10 117.5(6) . . ? O6 C9 Eu1 61.5(4) . . ? O5 C9 Eu1 60.1(3) . . ? C10 C9 Eu1 165.0(5) . . ? C9 C10 C11 113.9(6) . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C11 C11 C10 112.5(7) 3_666 . ? C11 C11 H11A 109.1 3_666 . ? C10 C11 H11A 109.1 . . ? C11 C11 H11B 109.1 3_666 . ? C10 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C1 O1 Eu1 92.7(4) . . ? Eu1 O1W H1WA 122(5) . . ? Eu1 O1W H1WB 123(5) . . ? H1WA O1W H1WB 114(7) . . ? C1 O2 Eu1 92.8(4) . . ? Eu1 O2W H8A 136(5) . . ? Eu1 O2W H8B 131(5) . . ? H8A O2W H8B 91(6) . . ? C8 O3 Eu1 155.8(4) . 1_565 ? C8 O3 Eu1 89.4(4) . 3_766 ? Eu1 O3 Eu1 114.65(17) 1_565 3_766 ? C8 O4 Eu1 101.1(4) . 3_766 ? C9 O5 Eu1 92.8(4) . . ? C9 O6 Eu1 92.6(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.878 _refine_diff_density_min -0.751 _refine_diff_density_rms 0.178 # Attachment '7.cif' data_wz-237 _database_code_depnum_ccdc_archive 'CCDC 725106' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H12 O8 Sm' _chemical_formula_weight 422.56 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.354(9) _cell_length_b 5.977(4) _cell_length_c 15.640(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.532(9) _cell_angle_gamma 90.00 _cell_volume 1246.0(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5847 _cell_measurement_theta_min 1.95 _cell_measurement_theta_max 24.99 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 4.749 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6183 _exptl_absorpt_correction_T_max 0.7231 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5847 _diffrn_reflns_av_R_equivalents 0.0705 _diffrn_reflns_av_sigmaI/netI 0.0854 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2194 _reflns_number_gt 1672 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0797P)^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 2194 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1490 _refine_ls_wR_factor_gt 0.1403 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.004 _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 0.86952(4) 0.91970(9) 0.41936(3) 0.0193(2) Uani 1 1 d . . . C1 C 0.9048(9) 0.760(2) 0.5990(7) 0.024(3) Uani 1 1 d . . . C2 C 0.9030(8) 0.7000(18) 0.6916(6) 0.018(2) Uani 1 1 d . . . C3 C 0.8447(9) 0.832(2) 0.7415(7) 0.026(3) Uani 1 1 d . . . H6A H 0.8138 0.9587 0.7174 0.032 Uiso 1 1 calc R . . C4 C 0.8312(9) 0.782(2) 0.8250(7) 0.026(3) Uani 1 1 d . . . H5A H 0.7916 0.8739 0.8571 0.031 Uiso 1 1 calc R . . C5 C 0.8767(10) 0.593(2) 0.8621(7) 0.032(3) Uani 1 1 d . . . H4A H 0.8665 0.5543 0.9185 0.038 Uiso 1 1 calc R . . C6 C 0.9371(9) 0.467(2) 0.8130(8) 0.029(3) Uani 1 1 d . . . H3A H 0.9705 0.3445 0.8381 0.035 Uiso 1 1 calc R . . C7 C 0.9500(9) 0.5125(18) 0.7287(7) 0.019(2) Uani 1 1 d . . . C8 C 1.0118(8) 0.3615(19) 0.6772(7) 0.023(3) Uiso 1 1 d . . . C9 C 0.6821(9) 0.696(2) 0.4004(7) 0.025(3) Uani 1 1 d . . . C10 C 0.5930(10) 0.549(2) 0.4117(8) 0.031(3) Uani 1 1 d . . . H10A H 0.6144 0.3938 0.4091 0.038 Uiso 1 1 calc R . . H10B H 0.5443 0.5736 0.3640 0.038 Uiso 1 1 calc R . . C11 C 0.5417(9) 0.584(2) 0.4942(7) 0.027(3) Uani 1 1 d . . . H11A H 0.5140 0.7340 0.4946 0.033 Uiso 1 1 calc R . . H11B H 0.5911 0.5718 0.5421 0.033 Uiso 1 1 calc R . . O1 O 0.8338(6) 0.7026(14) 0.5484(5) 0.0264(19) Uani 1 1 d . . . O1W O 0.8360(8) 1.2488(17) 0.5054(6) 0.038(2) Uani 1 1 d . . . H5C H 0.817(12) 1.37(3) 0.486(10) 0.057 Uiso 1 1 d . . . H5B H 0.884(11) 1.28(3) 0.526(10) 0.057 Uiso 1 1 d . . . O2 O 0.9725(6) 0.8893(13) 0.5731(5) 0.0257(18) Uani 1 1 d . . . O2W O 0.8039(7) 1.1948(14) 0.3161(5) 0.037(2) Uani 1 1 d . . . H6B H 0.8152 1.1511 0.2658 0.056 Uiso 1 1 d R . . H6C H 0.8330 1.3193 0.3260 0.056 Uiso 1 1 d R . . O3 O 1.0651(6) 0.2114(15) 0.7153(5) 0.032(2) Uiso 1 1 d . . . O4 O 1.0108(6) 0.3848(13) 0.5968(5) 0.0246(18) Uiso 1 1 d . . . O5 O 0.7571(6) 0.6185(14) 0.3647(6) 0.034(2) Uani 1 1 d . . . O6 O 0.6850(6) 0.8956(13) 0.4293(5) 0.030(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 0.0253(4) 0.0107(3) 0.0216(4) 0.0000(2) 0.0002(2) -0.0008(3) C1 0.032(7) 0.013(6) 0.026(6) 0.000(5) -0.003(5) 0.006(5) C2 0.020(6) 0.019(6) 0.016(5) 0.007(4) 0.008(4) 0.001(5) C3 0.032(7) 0.017(6) 0.030(7) 0.002(5) -0.003(5) 0.001(5) C4 0.035(7) 0.024(7) 0.020(6) -0.003(5) 0.007(5) -0.002(5) C5 0.051(8) 0.027(7) 0.019(6) 0.000(5) 0.004(6) -0.006(6) C6 0.031(7) 0.020(7) 0.038(7) -0.003(5) 0.008(6) 0.014(5) C7 0.029(6) 0.013(6) 0.017(6) 0.005(4) 0.001(5) -0.002(5) C9 0.028(7) 0.028(7) 0.018(6) 0.005(5) 0.003(5) -0.010(5) C10 0.034(7) 0.020(7) 0.040(7) -0.008(5) 0.007(6) -0.001(6) C11 0.032(7) 0.022(7) 0.028(6) -0.002(5) 0.001(5) -0.003(6) O1 0.028(5) 0.026(5) 0.025(4) 0.005(3) -0.001(4) -0.007(4) O1W 0.051(6) 0.017(5) 0.044(6) -0.003(4) -0.004(5) 0.004(5) O2 0.025(4) 0.024(5) 0.028(4) 0.003(3) 0.004(4) -0.009(4) O2W 0.057(6) 0.026(5) 0.029(5) 0.003(4) -0.001(4) 0.006(4) O5 0.029(5) 0.026(5) 0.047(5) -0.017(4) 0.007(4) -0.009(4) O6 0.041(5) 0.011(4) 0.038(5) -0.003(3) 0.001(4) -0.002(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 O2 2.395(8) 3_776 ? Sm1 O2W 2.430(8) . ? Sm1 O1W 2.440(10) . ? Sm1 O4 2.445(8) 3_766 ? Sm1 O3 2.457(8) 3_766 ? Sm1 O5 2.463(8) . ? Sm1 O1 2.470(7) . ? Sm1 O6 2.482(9) . ? Sm1 O2 2.701(8) . ? Sm1 C8 2.813(12) 3_766 ? C1 O1 1.245(13) . ? C1 O2 1.276(13) . ? C1 C2 1.493(14) . ? C2 C3 1.384(15) . ? C2 C7 1.394(15) . ? C3 C4 1.362(15) . ? C3 H6A 0.9300 . ? C4 C5 1.390(17) . ? C4 H5A 0.9300 . ? C5 C6 1.376(16) . ? C5 H4A 0.9300 . ? C6 C7 1.367(15) . ? C6 H3A 0.9300 . ? C7 C8 1.493(16) . ? C8 O4 1.264(13) . ? C8 O3 1.270(13) . ? C8 Sm1 2.813(12) 3_766 ? C9 O5 1.264(14) . ? C9 O6 1.275(14) . ? C9 C10 1.501(16) . ? C10 C11 1.513(16) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C11 1.52(2) 3_666 ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? O1W H5C 0.80(17) . ? O1W H5B 0.71(15) . ? O2 Sm1 2.395(8) 3_776 ? O2W H6B 0.8499 . ? O2W H6C 0.8499 . ? O3 Sm1 2.457(8) 3_766 ? O4 Sm1 2.445(8) 3_766 ? 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 Sm1 O2W 89.5(3) 3_776 . ? O2 Sm1 O1W 77.3(3) 3_776 . ? O2W Sm1 O1W 75.6(3) . . ? O2 Sm1 O4 77.3(3) 3_776 3_766 ? O2W Sm1 O4 130.2(3) . 3_766 ? O1W Sm1 O4 143.1(3) . 3_766 ? O2 Sm1 O3 80.6(3) 3_776 3_766 ? O2W Sm1 O3 77.2(3) . 3_766 ? O1W Sm1 O3 144.8(3) . 3_766 ? O4 Sm1 O3 53.5(3) 3_766 3_766 ? O2 Sm1 O5 151.9(3) 3_776 . ? O2W Sm1 O5 94.4(3) . . ? O1W Sm1 O5 130.7(3) . . ? O4 Sm1 O5 79.0(3) 3_766 . ? O3 Sm1 O5 73.2(3) 3_766 . ? O2 Sm1 O1 115.1(2) 3_776 . ? O2W Sm1 O1 144.9(3) . . ? O1W Sm1 O1 85.5(3) . . ? O4 Sm1 O1 81.6(3) 3_766 . ? O3 Sm1 O1 129.0(3) 3_766 . ? O5 Sm1 O1 75.8(3) . . ? O2 Sm1 O6 154.0(3) 3_776 . ? O2W Sm1 O6 76.3(3) . . ? O1W Sm1 O6 78.2(3) . . ? O4 Sm1 O6 128.4(3) 3_766 . ? O3 Sm1 O6 116.2(3) 3_766 . ? O5 Sm1 O6 52.6(3) . . ? O1 Sm1 O6 71.1(3) . . ? O2 Sm1 O2 65.8(3) 3_776 . ? O2W Sm1 O2 141.3(3) . . ? O1W Sm1 O2 70.4(3) . . ? O4 Sm1 O2 75.0(2) 3_766 . ? O3 Sm1 O2 123.6(3) 3_766 . ? O5 Sm1 O2 121.7(3) . . ? O1 Sm1 O2 49.5(2) . . ? O6 Sm1 O2 113.1(2) . . ? O2 Sm1 C8 77.8(3) 3_776 3_766 ? O2W Sm1 C8 103.8(3) . 3_766 ? O1W Sm1 C8 155.0(3) . 3_766 ? O4 Sm1 C8 26.7(3) 3_766 3_766 ? O3 Sm1 C8 26.8(3) 3_766 3_766 ? O5 Sm1 C8 74.2(3) . 3_766 ? O1 Sm1 C8 105.6(3) . 3_766 ? O6 Sm1 C8 126.4(3) . 3_766 ? O2 Sm1 C8 99.5(3) . 3_766 ? O1 C1 O2 119.4(10) . . ? O1 C1 C2 119.6(11) . . ? O2 C1 C2 120.5(10) . . ? C3 C2 C7 118.6(10) . . ? C3 C2 C1 117.0(10) . . ? C7 C2 C1 124.3(10) . . ? C4 C3 C2 121.9(11) . . ? C4 C3 H6A 119.1 . . ? C2 C3 H6A 119.1 . . ? C3 C4 C5 119.9(11) . . ? C3 C4 H5A 120.1 . . ? C5 C4 H5A 120.1 . . ? C6 C5 C4 118.0(11) . . ? C6 C5 H4A 121.0 . . ? C4 C5 H4A 121.0 . . ? C7 C6 C5 122.7(11) . . ? C7 C6 H3A 118.6 . . ? C5 C6 H3A 118.6 . . ? C6 C7 C2 118.9(10) . . ? C6 C7 C8 120.4(10) . . ? C2 C7 C8 120.7(9) . . ? O4 C8 O3 121.0(10) . . ? O4 C8 C7 119.9(10) . . ? O3 C8 C7 119.1(10) . . ? O4 C8 Sm1 60.2(6) . 3_766 ? O3 C8 Sm1 60.8(6) . 3_766 ? C7 C8 Sm1 179.3(8) . 3_766 ? O5 C9 O6 119.5(10) . . ? O5 C9 C10 119.4(11) . . ? O6 C9 C10 121.0(11) . . ? C9 C10 C11 114.9(10) . . ? C9 C10 H10A 108.5 . . ? C11 C10 H10A 108.5 . . ? C9 C10 H10B 108.5 . . ? C11 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C10 C11 C11 112.5(12) . 3_666 ? C10 C11 H11A 109.1 . . ? C11 C11 H11A 109.1 3_666 . ? C10 C11 H11B 109.1 . . ? C11 C11 H11B 109.1 3_666 . ? H11A C11 H11B 107.8 . . ? C1 O1 Sm1 101.4(7) . . ? Sm1 O1W H5C 124(10) . . ? Sm1 O1W H5B 104(10) . . ? H5C O1W H5B 103(10) . . ? C1 O2 Sm1 155.9(7) . 3_776 ? C1 O2 Sm1 89.5(6) . . ? Sm1 O2 Sm1 114.2(3) 3_776 . ? Sm1 O2W H6B 109.2 . . ? Sm1 O2W H6C 109.2 . . ? H6B O2W H6C 109.5 . . ? C8 O3 Sm1 92.4(7) . 3_766 ? C8 O4 Sm1 93.1(7) . 3_766 ? C9 O5 Sm1 93.5(7) . . ? C9 O6 Sm1 92.3(7) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 3.747 _refine_diff_density_min -1.995 _refine_diff_density_rms 0.284 # Attachment '8.cif' data_wz-202 _database_code_depnum_ccdc_archive 'CCDC 725107' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H24 O16 Pr2' _chemical_formula_weight 826.23 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' 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 Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.2994(13) _cell_length_b 8.9181(18) _cell_length_c 12.448(3) _cell_angle_alpha 77.22(3) _cell_angle_beta 78.95(3) _cell_angle_gamma 71.00(3) _cell_volume 639.4(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3415 _cell_measurement_theta_min 1.69 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.146 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 402 _exptl_absorpt_coefficient_mu 3.845 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5364 _exptl_absorpt_correction_T_max 0.6575 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3415 _diffrn_reflns_av_R_equivalents 0.0107 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2745 _reflns_number_gt 2711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0323P)^2^+1.1407P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.49(2) _refine_ls_number_reflns 2745 _refine_ls_number_parameters 342 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0229 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0580 _refine_ls_wR_factor_gt 0.0577 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pr1 Pr 0.93107(4) 0.53386(3) 0.22824(3) 0.01593(13) Uani 1 1 d . . . Pr2 Pr 0.70656(4) 0.99538(3) 0.03310(2) 0.01755(14) Uani 1 1 d . . . C1 C 0.746(3) 0.6013(15) 0.0070(11) 0.019(3) Uani 1 1 d . . . C2 C 0.639(2) 0.6161(15) -0.0893(11) 0.021(3) Uani 1 1 d . . . C3 C 0.7759(14) 0.5675(12) -0.1874(7) 0.0273(19) Uani 1 1 d . . . H3A H 0.9310 0.5202 -0.1873 0.033 Uiso 1 1 calc R . . C4 C 0.680(2) 0.5899(14) -0.2839(9) 0.030(3) Uani 1 1 d . . . H4A H 0.7695 0.5572 -0.3481 0.036 Uiso 1 1 calc R . . C5 C 0.4486(15) 0.6618(12) -0.2826(7) 0.0331(19) Uani 1 1 d . . . H5A H 0.3845 0.6794 -0.3473 0.040 Uiso 1 1 calc R . . C6 C 0.3119(15) 0.7077(10) -0.1884(6) 0.0278(17) Uani 1 1 d . . . H6A H 0.1577 0.7576 -0.1904 0.033 Uiso 1 1 calc R . . C7 C 0.4021(13) 0.6803(8) -0.0901(6) 0.0206(15) Uani 1 1 d . . . C8 C 0.2362(12) 0.7091(8) 0.0139(5) 0.0165(14) Uiso 1 1 d . . . C9 C 1.2335(12) 0.1122(9) 0.2421(6) 0.0190(16) Uani 1 1 d . . . C10 C 1.1210(13) 0.0380(9) 0.3504(6) 0.0214(15) Uani 1 1 d . . . C11 C 1.1778(14) 0.0569(9) 0.4447(6) 0.0248(17) Uani 1 1 d . . . H11A H 1.2698 0.1214 0.4413 0.030 Uiso 1 1 calc R . . C12 C 1.0951(19) -0.0234(12) 0.5512(7) 0.040(2) Uani 1 1 d . . . H12C H 1.1369 -0.0145 0.6167 0.048 Uiso 1 1 calc R . . C13 C 0.953(2) -0.1136(13) 0.5531(9) 0.032(3) Uani 1 1 d . . . H13A H 0.8987 -0.1668 0.6206 0.038 Uiso 1 1 calc R . . C14 C 0.8909(15) -0.1254(12) 0.4585(7) 0.0273(19) Uani 1 1 d . . . H14A H 0.7914 -0.1842 0.4614 0.033 Uiso 1 1 calc R . . C15 C 0.975(2) -0.0499(15) 0.3551(9) 0.017(2) Uani 1 1 d . . . C16 C 0.884(2) -0.0478(16) 0.2489(10) 0.016(3) Uiso 1 1 d . . . C17 C 1.108(3) 0.472(2) 0.4362(11) 0.025(4) Uani 1 1 d . . . C18 C 1.209(3) 0.407(2) 0.5477(11) 0.037(4) Uani 1 1 d . . . H18A H 1.1698 0.4960 0.5875 0.044 Uiso 1 1 calc R . . H18B H 1.1322 0.3303 0.5912 0.044 Uiso 1 1 calc R . . C19 C 1.4606(14) 0.3258(11) 0.5450(6) 0.0335(19) Uani 1 1 d . . . H19A H 1.5407 0.4038 0.5093 0.040 Uiso 1 1 calc R . . H19B H 1.5056 0.2407 0.5010 0.040 Uiso 1 1 calc R . . C20 C 1.5284(16) 0.2551(11) 0.6604(7) 0.034(2) Uani 1 1 d . . . H20A H 1.6920 0.2258 0.6553 0.041 Uiso 1 1 calc R . . H20B H 1.4652 0.3377 0.7067 0.041 Uiso 1 1 calc R . . C21 C 1.454(3) 0.1102(17) 0.7164(11) 0.029(3) Uani 1 1 d . . . H21C H 1.2897 0.1386 0.7252 0.035 Uiso 1 1 calc R . . H21D H 1.5143 0.0266 0.6709 0.035 Uiso 1 1 calc R . . C22 C 1.533(3) 0.050(2) 0.8257(14) 0.034(4) Uani 1 1 d . . . O1W O 0.5283(10) 0.6833(8) 0.3061(7) 0.0323(15) Uani 1 1 d . . . H1WA H 0.447(18) 0.641(13) 0.313(8) 0.039 Uiso 1 1 d . . . H1WB H 0.515(18) 0.774(14) 0.272(9) 0.039 Uiso 1 1 d . . . O1 O 0.6947(10) 0.7124(6) 0.0646(4) 0.0233(12) Uani 1 1 d . . . O2W O 0.6825(16) 0.3617(11) 0.2630(7) 0.037(2) Uani 1 1 d . . . H2WA H 0.550(19) 0.386(13) 0.324(9) 0.045 Uiso 1 1 d . . . H2WB H 0.71(3) 0.35(2) 0.319(14) 0.056 Uiso 1 1 d . . . O2 O 0.8929(11) 0.4673(7) 0.0410(5) 0.0296(13) Uani 1 1 d . . . O3W O 0.4774(18) 1.2853(11) 0.0215(9) 0.044(3) Uani 1 1 d D . . H3WA H 0.375(14) 1.296(15) 0.071(7) 0.053 Uiso 1 1 d D . . H3WB H 0.47(2) 1.375(6) -0.010(9) 0.053 Uiso 1 1 d D . . O3 O 0.2531(9) 0.5982(7) 0.0974(4) 0.0263(12) Uiso 1 1 d . . . O4W O 0.9432(15) 1.1831(11) -0.0505(8) 0.036(2) Uani 1 1 d . . . H4WA H 1.0776 1.1312 -0.0563 0.054 Uiso 1 1 calc R . . H4WB H 0.900(19) 1.261(14) 0.007(9) 0.054 Uiso 1 1 d . . . O4 O 0.0829(13) 0.8393(9) 0.0060(6) 0.0381(19) Uiso 1 1 d . . . O5 O 1.1848(15) 0.2607(10) 0.2204(7) 0.0298(19) Uani 1 1 d . . . O6 O 1.3738(9) 0.0118(7) 0.1855(4) 0.0235(11) Uiso 1 1 d . . . O7 O 0.8347(11) 0.0767(8) 0.1864(5) 0.0308(16) Uiso 1 1 d . . . O8 O 0.8636(11) -0.1805(8) 0.2369(5) 0.0292(16) Uiso 1 1 d . . . O9 O 1.2362(13) 0.4985(11) 0.3477(6) 0.0256(19) Uani 1 1 d . . . O10 O 0.9130(12) 0.4710(9) 0.4354(6) 0.0321(17) Uani 1 1 d . . . O11 O 1.7472(12) -0.0191(10) 0.8314(6) 0.0392(19) Uani 1 1 d . . . O12 O 1.4019(17) 0.0546(12) 0.9158(8) 0.034(2) Uiso 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 Pr1 0.0150(3) 0.0141(3) 0.0179(3) -0.0021(2) -0.0027(2) -0.0034(2) Pr2 0.0161(3) 0.0159(3) 0.0190(3) -0.0024(2) -0.0034(2) -0.0024(2) C1 0.024(5) 0.010(5) 0.024(5) 0.000(3) 0.002(3) -0.014(4) C2 0.024(6) 0.010(5) 0.025(5) 0.000(4) 0.000(4) -0.005(4) C3 0.016(4) 0.025(5) 0.038(5) -0.012(4) 0.003(3) 0.000(4) C4 0.038(6) 0.033(7) 0.021(5) -0.015(4) -0.002(4) -0.009(5) C5 0.034(5) 0.039(6) 0.029(4) -0.003(4) -0.014(4) -0.011(4) C6 0.031(4) 0.027(4) 0.024(4) 0.000(3) -0.011(3) -0.006(3) C7 0.026(4) 0.013(4) 0.023(4) -0.003(3) -0.002(3) -0.006(3) C9 0.015(4) 0.020(4) 0.022(4) -0.003(3) -0.008(3) -0.002(3) C10 0.019(4) 0.021(4) 0.023(4) -0.008(3) -0.004(3) -0.001(3) C11 0.026(4) 0.018(4) 0.036(4) -0.016(3) 0.006(4) -0.012(3) C12 0.057(7) 0.037(6) 0.021(4) -0.007(4) -0.018(4) -0.001(5) C13 0.041(6) 0.024(6) 0.027(5) -0.002(4) 0.001(4) -0.011(5) C14 0.027(5) 0.031(5) 0.027(4) -0.009(4) -0.004(4) -0.009(4) C15 0.023(5) 0.015(5) 0.013(5) -0.003(4) -0.008(4) -0.003(4) C17 0.016(7) 0.040(8) 0.014(6) -0.003(5) -0.003(5) -0.001(5) C18 0.027(6) 0.057(10) 0.022(6) -0.001(6) -0.006(5) -0.009(6) C19 0.025(4) 0.045(5) 0.027(4) 0.003(4) -0.006(4) -0.010(4) C20 0.038(5) 0.037(5) 0.034(4) 0.001(4) -0.012(4) -0.018(4) C21 0.034(7) 0.031(7) 0.024(6) -0.002(5) -0.010(5) -0.010(5) C22 0.038(9) 0.040(8) 0.038(8) -0.014(6) -0.003(7) -0.027(7) O1W 0.014(3) 0.019(3) 0.059(5) -0.005(3) -0.003(3) -0.001(2) O1 0.038(3) 0.015(3) 0.023(3) -0.007(2) -0.009(3) -0.011(2) O2W 0.025(4) 0.025(4) 0.062(6) -0.012(4) 0.003(4) -0.010(3) O2 0.031(3) 0.020(3) 0.033(3) -0.011(2) -0.019(3) 0.011(3) O3W 0.039(5) 0.019(5) 0.065(6) -0.005(4) 0.003(4) -0.002(4) O4W 0.022(4) 0.029(4) 0.054(5) 0.000(4) -0.002(4) -0.008(3) O5 0.027(4) 0.019(4) 0.038(4) -0.005(3) 0.002(3) -0.003(3) O9 0.014(3) 0.046(4) 0.016(3) 0.002(3) -0.003(2) -0.011(3) O10 0.020(3) 0.051(5) 0.024(3) -0.006(3) -0.004(2) -0.008(3) O11 0.023(4) 0.055(5) 0.032(3) -0.015(4) -0.005(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 Pr1 O2W 2.451(8) . ? Pr1 O5 2.452(9) . ? Pr1 O8 2.466(7) 1_565 ? Pr1 O3 2.485(5) 1_655 ? Pr1 O10 2.504(7) . ? Pr1 O9 2.549(8) . ? Pr1 O1W 2.565(6) . ? Pr1 O2 2.601(5) . ? Pr1 O1 2.662(5) . ? Pr1 C17 2.886(14) . ? Pr1 C1 3.057(14) . ? Pr1 H2WB 2.44(17) . ? Pr2 O4 2.329(8) 1_655 ? Pr2 O12 2.484(10) 1_464 ? Pr2 O1 2.490(5) . ? Pr2 O11 2.503(7) 1_464 ? Pr2 O3W 2.505(10) . ? Pr2 O4W 2.524(8) . ? Pr2 O7 2.531(6) 1_565 ? Pr2 O6 2.532(5) 1_465 ? Pr2 O8 2.841(6) 1_565 ? Pr2 C22 2.875(17) 1_464 ? Pr2 C16 3.006(13) 1_565 ? C1 O1 1.272(14) . ? C1 O2 1.292(15) . ? C1 C2 1.445(19) . ? C2 C7 1.416(16) . ? C2 C3 1.417(16) . ? C3 C4 1.394(14) . ? C3 H3A 0.9300 . ? C4 C5 1.386(15) . ? C4 H4A 0.9300 . ? C5 C6 1.371(11) . ? C5 H5A 0.9300 . ? C6 C7 1.387(11) . ? C6 H6A 0.9300 . ? C7 C8 1.513(10) . ? C8 O4 1.244(11) . ? C8 O3 1.260(8) . ? C9 O5 1.237(11) . ? C9 O6 1.266(9) . ? C9 C10 1.517(10) . ? C10 C11 1.350(11) . ? C10 C15 1.373(14) . ? C11 C12 1.450(12) . ? C11 H11A 0.9300 . ? C12 C13 1.381(15) . ? C12 H12C 0.9300 . ? C13 C14 1.343(15) . ? C13 H13A 0.9300 . ? C14 C15 1.408(14) . ? C14 H14A 0.9300 . ? C15 C16 1.532(17) . ? C16 O7 1.192(14) . ? C16 O8 1.276(14) . ? C16 Pr2 3.006(13) 1_545 ? C17 O10 1.237(17) . ? C17 O9 1.259(16) . ? C17 C18 1.550(19) . ? C18 C19 1.512(18) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.518(11) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.501(15) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.47(2) . ? C21 H21C 0.9700 . ? C21 H21D 0.9700 . ? C22 O12 1.260(19) . ? C22 O11 1.29(2) . ? C22 Pr2 2.875(17) 1_646 ? O1W H1WA 0.71(10) . ? O1W H1WB 0.81(11) . ? O2W H2WA 1.02(11) . ? O2W H2WB 0.73(16) . ? O3W H3WA 0.80(2) . ? O3W H3WB 0.79(2) . ? O3 Pr1 2.485(5) 1_455 ? O4W H4WA 0.8200 . ? O4W H4WB 1.05(11) . ? O4 Pr2 2.329(8) 1_455 ? O6 Pr2 2.532(5) 1_645 ? O7 Pr2 2.531(6) 1_545 ? O8 Pr1 2.466(7) 1_545 ? O8 Pr2 2.841(6) 1_545 ? O11 Pr2 2.503(7) 1_646 ? O12 Pr2 2.483(10) 1_646 ? 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 O2W Pr1 O5 74.6(3) . . ? O2W Pr1 O8 133.3(3) . 1_565 ? O5 Pr1 O8 151.4(3) . 1_565 ? O2W Pr1 O3 142.1(3) . 1_655 ? O5 Pr1 O3 80.3(2) . 1_655 ? O8 Pr1 O3 77.78(19) 1_565 1_655 ? O2W Pr1 O10 82.7(3) . . ? O5 Pr1 O10 88.7(3) . . ? O8 Pr1 O10 89.0(2) 1_565 . ? O3 Pr1 O10 125.11(19) 1_655 . ? O2W Pr1 O9 124.1(3) . . ? O5 Pr1 O9 74.9(3) . . ? O8 Pr1 O9 81.5(3) 1_565 . ? O3 Pr1 O9 74.2(2) 1_655 . ? O10 Pr1 O9 51.1(2) . . ? O2W Pr1 O1W 69.2(3) . . ? O5 Pr1 O1W 141.2(3) . . ? O8 Pr1 O1W 64.4(2) 1_565 . ? O3 Pr1 O1W 138.1(2) 1_655 . ? O10 Pr1 O1W 73.5(2) . . ? O9 Pr1 O1W 114.9(3) . . ? O2W Pr1 O2 70.6(3) . . ? O5 Pr1 O2 74.2(2) . . ? O8 Pr1 O2 117.11(19) 1_565 . ? O3 Pr1 O2 75.5(2) 1_655 . ? O10 Pr1 O2 151.1(2) . . ? O9 Pr1 O2 139.6(2) . . ? O1W Pr1 O2 105.5(2) . . ? O2W Pr1 O1 87.6(2) . . ? O5 Pr1 O1 123.3(2) . . ? O8 Pr1 O1 71.91(18) 1_565 . ? O3 Pr1 O1 82.84(18) 1_655 . ? O10 Pr1 O1 142.6(2) . . ? O9 Pr1 O1 148.0(2) . . ? O1W Pr1 O1 69.2(2) . . ? O2 Pr1 O1 49.14(16) . . ? O2W Pr1 C17 103.7(4) . . ? O5 Pr1 C17 81.2(4) . . ? O8 Pr1 C17 84.6(4) 1_565 . ? O3 Pr1 C17 99.9(3) 1_655 . ? O10 Pr1 C17 25.3(3) . . ? O9 Pr1 C17 25.8(3) . . ? O1W Pr1 C17 94.1(4) . . ? O2 Pr1 C17 155.4(3) . . ? O1 Pr1 C17 155.3(3) . . ? O2W Pr1 C1 76.8(3) . . ? O5 Pr1 C1 99.0(3) . . ? O8 Pr1 C1 95.0(3) 1_565 . ? O3 Pr1 C1 79.6(3) 1_655 . ? O10 Pr1 C1 155.2(3) . . ? O9 Pr1 C1 153.7(3) . . ? O1W Pr1 C1 86.1(3) . . ? O2 Pr1 C1 24.8(3) . . ? O1 Pr1 C1 24.5(3) . . ? C17 Pr1 C1 179.5(5) . . ? O2W Pr1 H2WB 17(4) . . ? O5 Pr1 H2WB 73(4) . . ? O8 Pr1 H2WB 131(4) 1_565 . ? O3 Pr1 H2WB 151(4) 1_655 . ? O10 Pr1 H2WB 66(4) . . ? O9 Pr1 H2WB 108(4) . . ? O1W Pr1 H2WB 68(4) . . ? O2 Pr1 H2WB 87(4) . . ? O1 Pr1 H2WB 103(4) . . ? C17 Pr1 H2WB 87(4) . . ? C1 Pr1 H2WB 94(4) . . ? O4 Pr2 O12 129.1(3) 1_655 1_464 ? O4 Pr2 O1 74.6(2) 1_655 . ? O12 Pr2 O1 85.0(3) 1_464 . ? O4 Pr2 O11 79.7(2) 1_655 1_464 ? O12 Pr2 O11 51.9(3) 1_464 1_464 ? O1 Pr2 O11 84.8(2) . 1_464 ? O4 Pr2 O3W 139.6(3) 1_655 . ? O12 Pr2 O3W 70.4(4) 1_464 . ? O1 Pr2 O3W 145.7(3) . . ? O11 Pr2 O3W 97.4(3) 1_464 . ? O4 Pr2 O4W 72.2(3) 1_655 . ? O12 Pr2 O4W 108.1(3) 1_464 . ? O1 Pr2 O4W 145.2(3) . . ? O11 Pr2 O4W 79.2(3) 1_464 . ? O3W Pr2 O4W 67.7(3) . . ? O4 Pr2 O7 83.9(2) 1_655 1_565 ? O12 Pr2 O7 145.9(3) 1_464 1_565 ? O1 Pr2 O7 116.29(19) . 1_565 ? O11 Pr2 O7 148.6(2) 1_464 1_565 ? O3W Pr2 O7 78.3(3) . 1_565 ? O4W Pr2 O7 70.3(3) . 1_565 ? O4 Pr2 O6 137.5(2) 1_655 1_465 ? O12 Pr2 O6 81.4(3) 1_464 1_465 ? O1 Pr2 O6 80.70(19) . 1_465 ? O11 Pr2 O6 132.1(2) 1_464 1_465 ? O3W Pr2 O6 72.5(3) . 1_465 ? O4W Pr2 O6 132.2(3) . 1_465 ? O7 Pr2 O6 76.73(18) 1_565 1_465 ? O4 Pr2 O8 68.4(2) 1_655 1_565 ? O12 Pr2 O8 143.8(3) 1_464 1_565 ? O1 Pr2 O8 68.52(17) . 1_565 ? O11 Pr2 O8 142.5(2) 1_464 1_565 ? O3W Pr2 O8 119.6(3) . 1_565 ? O4W Pr2 O8 107.7(3) . 1_565 ? O7 Pr2 O8 47.84(19) 1_565 1_565 ? O6 Pr2 O8 70.59(17) 1_465 1_565 ? O4 Pr2 C22 106.2(4) 1_655 1_464 ? O12 Pr2 C22 25.9(4) 1_464 1_464 ? O1 Pr2 C22 88.7(3) . 1_464 ? O11 Pr2 C22 26.7(4) 1_464 1_464 ? O3W Pr2 C22 79.5(5) . 1_464 ? O4W Pr2 C22 90.5(4) . 1_464 ? O7 Pr2 C22 154.9(4) 1_565 1_464 ? O6 Pr2 C22 107.3(4) 1_465 1_464 ? O8 Pr2 C22 157.2(3) 1_565 1_464 ? O4 Pr2 C16 74.9(3) 1_655 1_565 ? O12 Pr2 C16 153.9(3) 1_464 1_565 ? O1 Pr2 C16 93.5(3) . 1_565 ? O11 Pr2 C16 154.0(3) 1_464 1_565 ? O3W Pr2 C16 98.4(4) . 1_565 ? O4W Pr2 C16 87.9(3) . 1_565 ? O7 Pr2 C16 22.9(3) 1_565 1_565 ? O6 Pr2 C16 72.7(3) 1_465 1_565 ? O8 Pr2 C16 25.0(3) 1_565 1_565 ? C22 Pr2 C16 177.7(5) 1_464 1_565 ? O1 C1 O2 117.2(12) . . ? O1 C1 C2 123.1(13) . . ? O2 C1 C2 119.6(11) . . ? O1 C1 Pr1 60.1(6) . . ? O2 C1 Pr1 57.4(6) . . ? C2 C1 Pr1 171.3(8) . . ? C7 C2 C3 118.5(11) . . ? C7 C2 C1 122.4(11) . . ? C3 C2 C1 119.2(12) . . ? C4 C3 C2 120.6(10) . . ? C4 C3 H3A 119.7 . . ? C2 C3 H3A 119.7 . . ? C5 C4 C3 118.8(9) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? C6 C5 C4 121.8(8) . . ? C6 C5 H5A 119.1 . . ? C4 C5 H5A 119.1 . . ? C5 C6 C7 120.4(8) . . ? C5 C6 H6A 119.8 . . ? C7 C6 H6A 119.8 . . ? C6 C7 C2 119.7(8) . . ? C6 C7 C8 117.0(7) . . ? C2 C7 C8 123.1(8) . . ? O4 C8 O3 125.4(7) . . ? O4 C8 C7 115.6(6) . . ? O3 C8 C7 118.9(6) . . ? O5 C9 O6 127.4(7) . . ? O5 C9 C10 117.7(7) . . ? O6 C9 C10 114.9(6) . . ? C11 C10 C15 120.4(8) . . ? C11 C10 C9 116.5(7) . . ? C15 C10 C9 123.1(7) . . ? C10 C11 C12 119.8(7) . . ? C10 C11 H11A 120.1 . . ? C12 C11 H11A 120.1 . . ? C13 C12 C11 118.3(8) . . ? C13 C12 H12C 120.8 . . ? C11 C12 H12C 120.8 . . ? C14 C13 C12 120.8(10) . . ? C14 C13 H13A 119.6 . . ? C12 C13 H13A 119.6 . . ? C13 C14 C15 120.7(9) . . ? C13 C14 H14A 119.7 . . ? C15 C14 H14A 119.7 . . ? C10 C15 C14 119.9(9) . . ? C10 C15 C16 119.3(10) . . ? C14 C15 C16 120.4(10) . . ? O7 C16 O8 125.8(12) . . ? O7 C16 C15 117.9(11) . . ? O8 C16 C15 116.3(11) . . ? O7 C16 Pr2 55.6(6) . 1_545 ? O8 C16 Pr2 70.2(6) . 1_545 ? C15 C16 Pr2 173.5(9) . 1_545 ? O10 C17 O9 121.7(12) . . ? O10 C17 C18 117.4(12) . . ? O9 C17 C18 119.7(13) . . ? O10 C17 Pr1 59.8(6) . . ? O9 C17 Pr1 61.9(6) . . ? C18 C17 Pr1 169.6(11) . . ? C19 C18 C17 118.8(11) . . ? C19 C18 H18A 107.6 . . ? C17 C18 H18A 107.6 . . ? C19 C18 H18B 107.6 . . ? C17 C18 H18B 107.6 . . ? H18A C18 H18B 107.0 . . ? C18 C19 C20 112.2(8) . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C21 C20 C19 114.7(8) . . ? C21 C20 H20A 108.6 . . ? C19 C20 H20A 108.6 . . ? C21 C20 H20B 108.6 . . ? C19 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? C22 C21 C20 109.8(11) . . ? C22 C21 H21C 109.7 . . ? C20 C21 H21C 109.7 . . ? C22 C21 H21D 109.7 . . ? C20 C21 H21D 109.7 . . ? H21C C21 H21D 108.2 . . ? O12 C22 O11 117.5(15) . . ? O12 C22 C21 123.1(16) . . ? O11 C22 C21 119.4(14) . . ? O12 C22 Pr2 59.4(8) . 1_646 ? O11 C22 Pr2 60.4(7) . 1_646 ? C21 C22 Pr2 168.2(10) . 1_646 ? Pr1 O1W H1WA 116(9) . . ? Pr1 O1W H1WB 101(7) . . ? H1WA O1W H1WB 125(10) . . ? C1 O1 Pr2 136.7(7) . . ? C1 O1 Pr1 95.5(7) . . ? Pr2 O1 Pr1 110.57(18) . . ? Pr1 O2W H2WA 116(6) . . ? Pr1 O2W H2WB 80(10) . . ? H2WA O2W H2WB 65(10) . . ? C1 O2 Pr1 97.8(7) . . ? Pr2 O3W H3WA 110(9) . . ? Pr2 O3W H3WB 146(9) . . ? H3WA O3W H3WB 103(10) . . ? C8 O3 Pr1 125.5(5) . 1_455 ? Pr2 O4W H4WA 109.5 . . ? Pr2 O4W H4WB 103(6) . . ? H4WA O4W H4WB 113.0 . . ? C8 O4 Pr2 152.9(6) . 1_455 ? C9 O5 Pr1 153.7(7) . . ? C9 O6 Pr2 140.1(5) . 1_645 ? C16 O7 Pr2 101.6(7) . 1_545 ? C16 O8 Pr1 164.0(8) . 1_545 ? C16 O8 Pr2 84.8(7) . 1_545 ? Pr1 O8 Pr2 105.7(2) 1_545 1_545 ? C17 O9 Pr1 92.2(8) . . ? C17 O10 Pr1 94.9(7) . . ? C22 O11 Pr2 92.9(8) . 1_646 ? C22 O12 Pr2 94.7(10) . 1_646 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.498 _refine_diff_density_min -0.767 _refine_diff_density_rms 0.096