# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_6 _database_code_depnum_ccdc_archive 'CCDC 906608' #TrackingRef '906608.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Dy O10' _chemical_formula_weight 453.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9378(18) _cell_length_b 15.708(3) _cell_length_c 8.9066(18) _cell_angle_alpha 90.00 _cell_angle_beta 100.67(3) _cell_angle_gamma 90.00 _cell_volume 1228.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1085 _cell_measurement_theta_min 2.5105 _cell_measurement_theta_max 28.7933 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 6.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4597 _exptl_absorpt_correction_T_max 0.5790 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number 3908 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6964 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.0585 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2171 _reflns_number_gt 1710 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _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^)+(0.0329P)^2^+0.6660P] 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 2171 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0799 _refine_ls_goodness_of_fit_ref 1.148 _refine_ls_restrained_S_all 1.148 _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 Dy1 Dy 0.95238(4) 0.12614(3) 0.99361(4) 0.01648(14) Uani 1 1 d . . . C1 C 0.3165(9) 0.0900(5) 0.5140(9) 0.0160(19) Uani 1 1 d . . . C2 C 0.3254(9) 0.1336(5) 0.3768(8) 0.0163(18) Uani 1 1 d . . . C3 C 0.4615(10) 0.1703(6) 0.3618(9) 0.021(2) Uani 1 1 d . . . H3 H 0.4690 0.1969 0.2702 0.026 Uiso 1 1 calc R . . C4 C 0.5873(10) 0.1690(5) 0.4780(9) 0.019(2) Uani 1 1 d . . . H4 H 0.6773 0.1960 0.4671 0.023 Uiso 1 1 calc R . . C5 C 0.5753(9) 0.1260(6) 0.6122(9) 0.0210(18) Uani 1 1 d . . . C6 C 0.4402(9) 0.0867(5) 0.6297(9) 0.0185(19) Uani 1 1 d . . . H6 H 0.4341 0.0583 0.7200 0.022 Uiso 1 1 calc R . . C7 C 0.1652(10) 0.0003(5) 0.6512(10) 0.023(2) Uani 1 1 d . . . H7B H 0.2634 -0.0247 0.6923 0.027 Uiso 1 1 calc R . . H7A H 0.0947 -0.0458 0.6177 0.027 Uiso 1 1 calc R . . C8 C 0.1100(10) 0.0490(5) 0.7762(9) 0.020(2) Uani 1 1 d . . . C9 C 0.1926(10) 0.1379(5) 0.2450(9) 0.019(2) Uani 1 1 d . . . C10 C 0.7087(9) 0.1261(6) 0.7439(8) 0.0152(17) Uani 1 1 d . . . O1 O 0.1794(6) 0.0519(4) 0.5219(6) 0.0268(15) Uani 1 1 d . . . O2 O 0.0894(7) 0.1278(4) 0.7692(6) 0.0274(14) Uani 1 1 d . . . O3 O 0.0723(6) 0.0064(3) 0.8837(6) 0.0171(13) Uani 1 1 d . . . O4 O 0.0599(6) 0.1503(3) 0.2649(6) 0.0197(14) Uani 1 1 d . . . O5 O 0.2190(6) 0.1309(4) 0.1100(6) 0.0256(14) Uani 1 1 d . . . O6 O 0.7867(7) 0.1934(4) 0.7732(7) 0.0262(15) Uani 1 1 d . . . O7 O 0.7418(7) 0.0596(4) 0.8220(6) 0.0276(15) Uani 1 1 d . . . O8 O 0.7497(7) 0.1584(4) 1.1133(7) 0.0246(14) Uani 1 1 d . . . H8B H 0.7516 0.2069 1.1556 0.030 Uiso 1 1 d R . . H8A H 0.6597 0.1443 1.0725 0.030 Uiso 1 1 d R . . O9 O 0.9936(7) 0.2721(4) 1.0115(6) 0.0252(15) Uani 1 1 d . . . H9B H 1.0430 0.3045 1.0796 0.030 Uiso 1 1 d R . . H9A H 0.9825 0.2952 0.9240 0.030 Uiso 1 1 d R . . O10 O 0.485(3) 0.0683(11) 0.036(2) 0.048(5) Uani 0.50 1 d P A 1 O10' O 0.460(2) 0.1128(14) -0.009(2) 0.049(5) Uani 0.50 1 d P B 2 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 Dy1 0.0163(2) 0.0195(2) 0.0131(2) 0.00050(19) 0.00122(15) -0.0006(2) C1 0.013(4) 0.023(4) 0.012(4) -0.004(3) 0.005(4) -0.007(4) C2 0.014(4) 0.024(5) 0.010(4) -0.003(4) -0.002(3) 0.005(4) C3 0.017(5) 0.032(5) 0.013(4) 0.008(4) -0.003(4) -0.006(4) C4 0.015(5) 0.027(5) 0.013(4) 0.004(4) -0.004(4) -0.009(4) C5 0.020(4) 0.025(4) 0.016(4) 0.000(4) 0.001(4) 0.006(5) C6 0.014(5) 0.020(4) 0.020(5) 0.005(4) 0.000(4) -0.003(4) C7 0.023(5) 0.028(5) 0.018(4) 0.005(4) 0.006(4) -0.004(4) C8 0.018(5) 0.024(5) 0.018(5) 0.000(4) 0.000(4) -0.002(4) C9 0.016(5) 0.020(5) 0.019(5) 0.006(4) -0.003(4) -0.006(4) C10 0.012(4) 0.023(4) 0.010(4) -0.001(4) 0.000(3) -0.005(4) O1 0.018(3) 0.044(4) 0.020(3) 0.009(3) 0.007(3) -0.006(3) O2 0.039(4) 0.024(3) 0.021(3) 0.004(3) 0.011(3) 0.004(4) O3 0.020(3) 0.017(3) 0.014(3) 0.002(2) 0.002(3) 0.001(2) O4 0.014(3) 0.032(4) 0.012(3) -0.003(2) -0.001(2) 0.004(3) O5 0.016(3) 0.048(4) 0.013(3) -0.001(3) 0.005(3) 0.002(3) O6 0.025(4) 0.028(4) 0.023(3) 0.006(3) -0.001(3) -0.007(3) O7 0.026(4) 0.027(3) 0.024(3) 0.005(3) -0.009(3) -0.001(3) O8 0.027(4) 0.021(3) 0.029(3) -0.004(3) 0.010(3) 0.005(3) O9 0.040(4) 0.021(3) 0.014(3) 0.001(2) 0.002(3) -0.009(3) O10 0.036(12) 0.049(12) 0.061(15) -0.004(9) 0.015(10) -0.005(10) O10' 0.025(9) 0.088(16) 0.032(10) -0.013(12) 0.000(7) -0.004(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 Dy1 O8 2.321(6) . ? Dy1 O9 2.324(6) . ? Dy1 O3 2.380(5) 3_657 ? Dy1 O5 2.418(5) 1_656 ? Dy1 O7 2.430(6) . ? Dy1 O3 2.456(5) 1_655 ? Dy1 O4 2.459(5) 1_656 ? Dy1 O6 2.467(6) . ? Dy1 O2 2.530(6) 1_655 ? Dy1 C9 2.807(8) 1_656 ? Dy1 C10 2.810(7) . ? Dy1 C8 2.866(9) 1_655 ? C1 C6 1.366(11) . ? C1 O1 1.377(9) . ? C1 C2 1.416(11) . ? C2 C3 1.375(11) . ? C2 C9 1.508(10) . ? C3 C4 1.380(11) . ? C3 H3 0.9300 . ? C4 C5 1.394(11) . ? C4 H4 0.9300 . ? C5 C6 1.391(12) . ? C5 C10 1.510(10) . ? C6 H6 0.9300 . ? C7 O1 1.433(9) . ? C7 C8 1.507(12) . ? C7 H7B 0.9700 . ? C7 H7A 0.9700 . ? C8 O2 1.251(9) . ? C8 O3 1.265(10) . ? C8 Dy1 2.866(9) 1_455 ? C9 O4 1.247(10) . ? C9 O5 1.272(10) . ? C9 Dy1 2.807(8) 1_454 ? C10 O7 1.259(10) . ? C10 O6 1.266(9) . ? O2 Dy1 2.530(6) 1_455 ? O3 Dy1 2.380(5) 3_657 ? O3 Dy1 2.456(5) 1_455 ? O4 Dy1 2.459(5) 1_454 ? O5 Dy1 2.418(5) 1_454 ? O8 H8B 0.8490 . ? O8 H8A 0.8481 . ? O9 H9B 0.8494 . ? O9 H9A 0.8485 . ? 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 O8 Dy1 O9 83.1(2) . . ? O8 Dy1 O3 80.42(19) . 3_657 ? O9 Dy1 O3 149.17(18) . 3_657 ? O8 Dy1 O5 126.0(2) . 1_656 ? O9 Dy1 O5 79.0(2) . 1_656 ? O3 Dy1 O5 89.9(2) 3_657 1_656 ? O8 Dy1 O7 78.7(2) . . ? O9 Dy1 O7 124.2(2) . . ? O3 Dy1 O7 77.64(19) 3_657 . ? O5 Dy1 O7 150.5(2) 1_656 . ? O8 Dy1 O3 141.7(2) . 1_655 ? O9 Dy1 O3 135.1(2) . 1_655 ? O3 Dy1 O3 66.3(2) 3_657 1_655 ? O5 Dy1 O3 74.14(19) 1_656 1_655 ? O7 Dy1 O3 76.37(19) . 1_655 ? O8 Dy1 O4 73.2(2) . 1_656 ? O9 Dy1 O4 75.66(18) . 1_656 ? O3 Dy1 O4 74.70(18) 3_657 1_656 ? O5 Dy1 O4 53.06(18) 1_656 1_656 ? O7 Dy1 O4 143.2(2) . 1_656 ? O3 Dy1 O4 112.95(18) 1_655 1_656 ? O8 Dy1 O6 82.4(2) . . ? O9 Dy1 O6 72.30(19) . . ? O3 Dy1 O6 130.32(19) 3_657 . ? O5 Dy1 O6 136.6(2) 1_656 . ? O7 Dy1 O6 53.33(19) . . ? O3 Dy1 O6 104.63(19) 1_655 . ? O4 Dy1 O6 141.60(19) 1_656 . ? O8 Dy1 O2 153.3(2) . 1_655 ? O9 Dy1 O2 87.15(19) . 1_655 ? O3 Dy1 O2 118.11(19) 3_657 1_655 ? O5 Dy1 O2 75.84(19) 1_656 1_655 ? O7 Dy1 O2 86.5(2) . 1_655 ? O3 Dy1 O2 51.85(18) 1_655 1_655 ? O4 Dy1 O2 128.05(19) 1_656 1_655 ? O6 Dy1 O2 71.0(2) . 1_655 ? O8 Dy1 C9 99.6(2) . 1_656 ? O9 Dy1 C9 78.0(2) . 1_656 ? O3 Dy1 C9 79.2(2) 3_657 1_656 ? O5 Dy1 C9 26.9(2) 1_656 1_656 ? O7 Dy1 C9 156.8(2) . 1_656 ? O3 Dy1 C9 92.4(2) 1_655 1_656 ? O4 Dy1 C9 26.4(2) 1_656 1_656 ? O6 Dy1 C9 149.8(2) . 1_656 ? O2 Dy1 C9 102.6(2) 1_655 1_656 ? O8 Dy1 C10 78.9(2) . . ? O9 Dy1 C10 98.3(2) . . ? O3 Dy1 C10 103.8(2) 3_657 . ? O5 Dy1 C10 153.8(2) 1_656 . ? O7 Dy1 C10 26.6(2) . . ? O3 Dy1 C10 90.9(2) 1_655 . ? O4 Dy1 C10 151.9(2) 1_656 . ? O6 Dy1 C10 26.8(2) . . ? O2 Dy1 C10 78.0(2) 1_655 . ? C9 Dy1 C10 176.2(2) 1_656 . ? O8 Dy1 C8 157.8(2) . 1_655 ? O9 Dy1 C8 111.8(2) . 1_655 ? O3 Dy1 C8 92.3(2) 3_657 1_655 ? O5 Dy1 C8 74.6(2) 1_656 1_655 ? O7 Dy1 C8 79.3(2) . 1_655 ? O3 Dy1 C8 26.1(2) 1_655 1_655 ? O4 Dy1 C8 125.3(2) 1_656 1_655 ? O6 Dy1 C8 86.6(2) . 1_655 ? O2 Dy1 C8 25.9(2) 1_655 1_655 ? C9 Dy1 C8 99.6(2) 1_656 1_655 ? C10 Dy1 C8 82.6(2) . 1_655 ? C6 C1 O1 123.3(7) . . ? C6 C1 C2 120.2(8) . . ? O1 C1 C2 116.5(7) . . ? C3 C2 C1 118.6(7) . . ? C3 C2 C9 119.2(7) . . ? C1 C2 C9 122.1(7) . . ? C2 C3 C4 122.2(8) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? C3 C4 C5 118.0(8) . . ? C3 C4 H4 121.0 . . ? C5 C4 H4 121.0 . . ? C6 C5 C4 121.1(7) . . ? C6 C5 C10 119.4(7) . . ? C4 C5 C10 119.4(8) . . ? C1 C6 C5 119.8(8) . . ? C1 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? O1 C7 C8 113.3(7) . . ? O1 C7 H7B 108.9 . . ? C8 C7 H7B 108.9 . . ? O1 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? H7B C7 H7A 107.7 . . ? O2 C8 O3 120.2(8) . . ? O2 C8 C7 122.1(7) . . ? O3 C8 C7 117.4(7) . . ? O2 C8 Dy1 61.9(4) . 1_455 ? O3 C8 Dy1 58.6(4) . 1_455 ? C7 C8 Dy1 169.3(6) . 1_455 ? O4 C9 O5 119.7(7) . . ? O4 C9 C2 121.9(7) . . ? O5 C9 C2 118.4(7) . . ? O4 C9 Dy1 61.1(4) . 1_454 ? O5 C9 Dy1 59.3(4) . 1_454 ? C2 C9 Dy1 173.4(6) . 1_454 ? O7 C10 O6 121.0(7) . . ? O7 C10 C5 119.9(7) . . ? O6 C10 C5 119.1(7) . . ? O7 C10 Dy1 59.7(4) . . ? O6 C10 Dy1 61.3(4) . . ? C5 C10 Dy1 178.7(6) . . ? C1 O1 C7 119.9(6) . . ? C8 O2 Dy1 92.3(5) . 1_455 ? C8 O3 Dy1 150.6(5) . 3_657 ? C8 O3 Dy1 95.4(5) . 1_455 ? Dy1 O3 Dy1 113.7(2) 3_657 1_455 ? C9 O4 Dy1 92.6(5) . 1_454 ? C9 O5 Dy1 93.9(5) . 1_454 ? C10 O6 Dy1 91.9(5) . . ? C10 O7 Dy1 93.8(5) . . ? Dy1 O8 H8B 116.5 . . ? Dy1 O8 H8A 120.3 . . ? H8B O8 H8A 111.3 . . ? Dy1 O9 H9B 133.9 . . ? Dy1 O9 H9A 111.6 . . ? H9B O9 H9A 110.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.6(13) . . . . ? O1 C1 C2 C3 -178.0(8) . . . . ? C6 C1 C2 C9 179.1(8) . . . . ? O1 C1 C2 C9 -0.5(12) . . . . ? C1 C2 C3 C4 -2.7(14) . . . . ? C9 C2 C3 C4 179.7(8) . . . . ? C2 C3 C4 C5 2.4(14) . . . . ? C3 C4 C5 C6 -1.0(14) . . . . ? C3 C4 C5 C10 -177.7(8) . . . . ? O1 C1 C6 C5 179.3(8) . . . . ? C2 C1 C6 C5 -0.3(13) . . . . ? C4 C5 C6 C1 0.0(13) . . . . ? C10 C5 C6 C1 176.7(8) . . . . ? O1 C7 C8 O2 -4.5(12) . . . . ? O1 C7 C8 O3 169.5(7) . . . . ? O1 C7 C8 Dy1 105(3) . . . 1_455 ? C3 C2 C9 O4 -140.6(8) . . . . ? C1 C2 C9 O4 41.9(12) . . . . ? C3 C2 C9 O5 37.4(12) . . . . ? C1 C2 C9 O5 -140.1(8) . . . . ? C3 C2 C9 Dy1 105(5) . . . 1_454 ? C1 C2 C9 Dy1 -73(5) . . . 1_454 ? C6 C5 C10 O7 42.7(12) . . . . ? C4 C5 C10 O7 -140.5(9) . . . . ? C6 C5 C10 O6 -137.9(8) . . . . ? C4 C5 C10 O6 38.8(12) . . . . ? C6 C5 C10 Dy1 -28(28) . . . . ? C4 C5 C10 Dy1 149(27) . . . . ? O8 Dy1 C10 O7 -86.8(5) . . . . ? O9 Dy1 C10 O7 -168.1(5) . . . . ? O3 Dy1 C10 O7 -9.7(5) 3_657 . . . ? O5 Dy1 C10 O7 110.1(6) 1_656 . . . ? O3 Dy1 C10 O7 56.0(5) 1_655 . . . ? O4 Dy1 C10 O7 -93.1(6) 1_656 . . . ? O6 Dy1 C10 O7 178.0(8) . . . . ? O2 Dy1 C10 O7 106.6(5) 1_655 . . . ? C9 Dy1 C10 O7 -153(3) 1_656 . . . ? C8 Dy1 C10 O7 80.8(5) 1_655 . . . ? O8 Dy1 C10 O6 95.1(5) . . . . ? O9 Dy1 C10 O6 13.9(5) . . . . ? O3 Dy1 C10 O6 172.3(4) 3_657 . . . ? O5 Dy1 C10 O6 -68.0(8) 1_656 . . . ? O7 Dy1 C10 O6 -178.0(8) . . . . ? O3 Dy1 C10 O6 -122.0(5) 1_655 . . . ? O4 Dy1 C10 O6 88.9(6) 1_656 . . . ? O2 Dy1 C10 O6 -71.4(5) 1_655 . . . ? C9 Dy1 C10 O6 29(4) 1_656 . . . ? C8 Dy1 C10 O6 -97.2(5) 1_655 . . . ? O8 Dy1 C10 C5 -16(27) . . . . ? O9 Dy1 C10 C5 -97(27) . . . . ? O3 Dy1 C10 C5 61(27) 3_657 . . . ? O5 Dy1 C10 C5 -179(100) 1_656 . . . ? O7 Dy1 C10 C5 71(27) . . . . ? O3 Dy1 C10 C5 127(27) 1_655 . . . ? O4 Dy1 C10 C5 -22(28) 1_656 . . . ? O6 Dy1 C10 C5 -111(27) . . . . ? O2 Dy1 C10 C5 178(100) 1_655 . . . ? C9 Dy1 C10 C5 -82(28) 1_656 . . . ? C8 Dy1 C10 C5 152(27) 1_655 . . . ? C6 C1 O1 C7 -5.1(12) . . . . ? C2 C1 O1 C7 174.5(7) . . . . ? C8 C7 O1 C1 92.6(9) . . . . ? O3 C8 O2 Dy1 -5.3(8) . . . 1_455 ? C7 C8 O2 Dy1 168.6(7) . . . 1_455 ? O2 C8 O3 Dy1 177.5(7) . . . 3_657 ? C7 C8 O3 Dy1 3.4(16) . . . 3_657 ? Dy1 C8 O3 Dy1 172.0(12) 1_455 . . 3_657 ? O2 C8 O3 Dy1 5.5(9) . . . 1_455 ? C7 C8 O3 Dy1 -168.7(7) . . . 1_455 ? O5 C9 O4 Dy1 8.9(8) . . . 1_454 ? C2 C9 O4 Dy1 -173.2(7) . . . 1_454 ? O4 C9 O5 Dy1 -9.0(8) . . . 1_454 ? C2 C9 O5 Dy1 172.9(6) . . . 1_454 ? O7 C10 O6 Dy1 -2.0(8) . . . . ? C5 C10 O6 Dy1 178.6(6) . . . . ? O8 Dy1 O6 C10 -80.4(5) . . . . ? O9 Dy1 O6 C10 -165.6(5) . . . . ? O3 Dy1 O6 C10 -9.9(6) 3_657 . . . ? O5 Dy1 O6 C10 143.5(5) 1_656 . . . ? O7 Dy1 O6 C10 1.1(5) . . . . ? O3 Dy1 O6 C10 61.2(5) 1_655 . . . ? O4 Dy1 O6 C10 -130.8(5) 1_656 . . . ? O2 Dy1 O6 C10 101.3(5) 1_655 . . . ? C9 Dy1 O6 C10 -176.3(5) 1_656 . . . ? C8 Dy1 O6 C10 80.2(5) 1_655 . . . ? O6 C10 O7 Dy1 2.0(8) . . . . ? C5 C10 O7 Dy1 -178.6(6) . . . . ? O8 Dy1 O7 C10 87.8(5) . . . . ? O9 Dy1 O7 C10 14.3(6) . . . . ? O3 Dy1 O7 C10 170.3(5) 3_657 . . . ? O5 Dy1 O7 C10 -122.7(5) 1_656 . . . ? O3 Dy1 O7 C10 -121.4(5) 1_655 . . . ? O4 Dy1 O7 C10 128.4(5) 1_656 . . . ? O6 Dy1 O7 C10 -1.1(5) . . . . ? O2 Dy1 O7 C10 -69.9(5) 1_655 . . . ? C9 Dy1 O7 C10 175.6(6) 1_656 . . . ? C8 Dy1 O7 C10 -94.9(5) 1_655 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.080 _refine_diff_density_min -0.989 _refine_diff_density_rms 0.179 data_8 _database_code_depnum_ccdc_archive 'CCDC 906609' #TrackingRef '906609.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Er O10' _chemical_formula_weight 458.45 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' Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9007(18) _cell_length_b 15.592(3) _cell_length_c 8.8728(18) _cell_angle_alpha 90.00 _cell_angle_beta 100.63(3) _cell_angle_gamma 90.00 _cell_volume 1210.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1085 _cell_measurement_theta_min 2.5105 _cell_measurement_theta_max 28.7933 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 6.989 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4876 _exptl_absorpt_correction_T_max 0.5416 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number 3908 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6892 _diffrn_reflns_av_R_equivalents 0.0676 _diffrn_reflns_av_sigmaI/netI 0.0650 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2139 _reflns_number_gt 1679 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _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^)+(0.0258P)^2^+4.1038P] 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 2139 _refine_ls_number_parameters 199 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0819 _refine_ls_goodness_of_fit_ref 1.191 _refine_ls_restrained_S_all 1.188 _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 Er1 Er 0.95343(5) 0.12549(3) 0.49369(5) 0.01649(15) Uani 1 1 d . . . C1 C 0.3165(10) 0.0900(6) 0.0133(11) 0.014(2) Uani 1 1 d . . . C2 C 0.3264(10) 0.1341(6) -0.1230(10) 0.014(2) Uani 1 1 d . . . C3 C 0.4633(10) 0.1712(6) -0.1400(11) 0.016(2) Uani 1 1 d U . . H3 H 0.4711 0.1982 -0.2316 0.019 Uiso 1 1 calc R . . C4 C 0.5896(11) 0.1685(7) -0.0215(11) 0.021(2) Uani 1 1 d . . . H4 H 0.6806 0.1952 -0.0320 0.025 Uiso 1 1 calc R . . C5 C 0.5780(10) 0.1259(7) 0.1114(10) 0.018(2) Uani 1 1 d . . . C6 C 0.4422(11) 0.0862(6) 0.1298(11) 0.018(2) Uani 1 1 d . . . H6 H 0.4365 0.0572 0.2202 0.021 Uiso 1 1 calc R . . C7 C 0.1662(11) 0.0002(6) 0.1505(11) 0.020(2) Uani 1 1 d . . . H7A H 0.2649 -0.0247 0.1924 0.024 Uiso 1 1 calc R . . H7B H 0.0959 -0.0464 0.1169 0.024 Uiso 1 1 calc R . . C8 C 0.1093(10) 0.0496(7) 0.2765(11) 0.015(2) Uani 1 1 d . . . C9 C 0.1934(10) 0.1369(6) -0.2564(11) 0.017(2) Uani 1 1 d . . . C10 C 0.7106(10) 0.1260(8) 0.2428(10) 0.018(2) Uani 1 1 d . . . O1 O 0.1808(7) 0.0513(4) 0.0214(8) 0.0235(17) Uani 1 1 d . . . O2 O 0.0901(7) 0.1283(5) 0.2710(7) 0.0236(16) Uani 1 1 d . . . O3 O 0.0736(7) 0.0059(4) 0.3846(7) 0.0154(15) Uani 1 1 d . . . O4 O 0.0601(7) 0.1499(4) -0.2352(7) 0.0175(16) Uani 1 1 d . . . O5 O 0.2190(7) 0.1306(5) -0.3900(7) 0.0265(17) Uani 1 1 d . . . O6 O 0.7886(7) 0.1943(5) 0.2734(7) 0.0225(17) Uani 1 1 d . . . O7 O 0.7429(8) 0.0601(5) 0.3242(8) 0.0295(19) Uani 1 1 d . . . O8 O 0.9945(7) 0.2709(4) 0.5108(7) 0.0211(16) Uani 1 1 d U . . H8A H 1.0451 0.2999 0.5862 0.025 Uiso 1 1 d R . . H8B H 0.9631 0.3019 0.4289 0.025 Uiso 1 1 d R . . O9 O 0.7514(8) 0.1580(4) 0.6122(8) 0.0254(18) Uani 1 1 d . . . H9A H 0.6568 0.1497 0.5794 0.030 Uiso 1 1 d R . . H9B H 0.7677 0.2085 0.6475 0.030 Uiso 1 1 d R . . O10 O 0.463(3) 0.1143(16) 0.492(3) 0.045(6) Uani 0.50 1 d P . . O10' O 0.479(3) 0.0675(12) 0.531(3) 0.034(6) Uani 0.50 1 d P . . 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 Er1 0.0149(2) 0.0206(3) 0.0132(2) 0.0001(2) 0.00075(15) -0.0007(2) C1 0.013(5) 0.021(6) 0.010(5) -0.006(4) 0.007(4) -0.005(4) C2 0.011(5) 0.016(6) 0.015(5) -0.002(5) 0.000(4) 0.004(4) C3 0.016(2) 0.016(2) 0.016(2) 0.0007(10) 0.0033(11) -0.0003(10) C4 0.012(5) 0.029(6) 0.021(6) 0.000(5) -0.001(4) -0.007(4) C5 0.019(5) 0.023(6) 0.010(5) 0.000(5) 0.000(4) 0.003(5) C6 0.021(6) 0.022(6) 0.010(5) 0.003(4) 0.003(4) 0.002(4) C7 0.017(5) 0.026(7) 0.016(6) 0.002(5) 0.001(5) -0.005(4) C8 0.009(5) 0.019(6) 0.017(6) -0.002(4) 0.001(4) -0.002(4) C9 0.017(5) 0.020(6) 0.016(5) 0.001(5) 0.003(4) -0.002(4) C10 0.015(5) 0.028(6) 0.011(5) 0.003(5) 0.001(4) 0.007(5) O1 0.023(4) 0.033(5) 0.015(4) 0.010(3) 0.005(3) -0.003(3) O2 0.030(4) 0.022(4) 0.019(4) 0.004(4) 0.006(3) 0.001(4) O3 0.016(4) 0.022(4) 0.008(3) 0.002(3) 0.003(3) 0.000(3) O4 0.015(4) 0.026(4) 0.010(4) 0.001(3) 0.000(3) 0.004(3) O5 0.015(3) 0.045(5) 0.018(4) -0.003(4) 0.000(3) 0.003(4) O6 0.018(4) 0.032(5) 0.015(4) 0.003(3) -0.002(3) -0.010(3) O7 0.022(4) 0.034(5) 0.027(5) 0.003(4) -0.009(3) 0.001(3) O8 0.0218(18) 0.0206(18) 0.0205(18) 0.0010(10) 0.0027(10) -0.0008(10) O9 0.020(4) 0.025(4) 0.032(5) 0.000(3) 0.007(3) 0.007(3) O10 0.025(10) 0.076(18) 0.035(12) -0.011(15) 0.009(8) -0.023(15) O10' 0.032(11) 0.031(13) 0.039(14) -0.005(10) 0.007(9) -0.012(10) _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 Er1 O8 2.296(7) . ? Er1 O9 2.301(6) . ? Er1 O3 2.349(6) 3_656 ? Er1 O5 2.400(6) 1_656 ? Er1 O7 2.402(7) . ? Er1 O3 2.437(6) 1_655 ? Er1 O4 2.447(6) 1_656 ? Er1 O6 2.463(7) . ? Er1 O2 2.504(6) 1_655 ? Er1 C9 2.787(9) 1_656 ? Er1 C8 2.833(10) 1_655 ? C1 O1 1.364(10) . ? C1 C6 1.377(13) . ? C1 C2 1.408(13) . ? C2 C3 1.382(12) . ? C2 C9 1.512(12) . ? C3 C4 1.391(13) . ? C3 H3 0.9300 . ? C4 C5 1.374(13) . ? C4 H4 0.9300 . ? C5 C6 1.395(13) . ? C5 C10 1.498(12) . ? C6 H6 0.9300 . ? C7 O1 1.420(11) . ? C7 C8 1.519(13) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O2 1.239(11) . ? C8 O3 1.264(11) . ? C8 Er1 2.833(10) 1_455 ? C9 O4 1.252(11) . ? C9 O5 1.252(11) . ? C9 Er1 2.787(9) 1_454 ? C10 O7 1.258(12) . ? C10 O6 1.274(12) . ? O2 Er1 2.504(6) 1_455 ? O3 Er1 2.349(6) 3_656 ? O3 Er1 2.437(6) 1_455 ? O4 Er1 2.447(6) 1_454 ? O5 Er1 2.400(6) 1_454 ? O8 H8A 0.8628 . ? O8 H8B 0.8750 . ? O9 H9A 0.8489 . ? O9 H9B 0.8496 . ? O10 O10' 0.81(2) . ? 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 O8 Er1 O9 83.1(2) . . ? O8 Er1 O3 149.2(2) . 3_656 ? O9 Er1 O3 80.0(2) . 3_656 ? O8 Er1 O5 78.9(2) . 1_656 ? O9 Er1 O5 125.9(2) . 1_656 ? O3 Er1 O5 90.4(2) 3_656 1_656 ? O8 Er1 O7 123.8(2) . . ? O9 Er1 O7 78.1(3) . . ? O3 Er1 O7 77.5(2) 3_656 . ? O5 Er1 O7 151.2(2) 1_656 . ? O8 Er1 O3 134.8(2) . 1_655 ? O9 Er1 O3 141.9(2) . 1_655 ? O3 Er1 O3 66.7(2) 3_656 1_655 ? O5 Er1 O3 74.1(2) 1_656 1_655 ? O7 Er1 O3 77.0(2) . 1_655 ? O8 Er1 O4 75.7(2) . 1_656 ? O9 Er1 O4 73.2(2) . 1_656 ? O3 Er1 O4 74.8(2) 3_656 1_656 ? O5 Er1 O4 53.1(2) 1_656 1_656 ? O7 Er1 O4 142.9(2) . 1_656 ? O3 Er1 O4 113.0(2) 1_655 1_656 ? O8 Er1 O6 71.7(2) . . ? O9 Er1 O6 82.3(2) . . ? O3 Er1 O6 130.4(2) 3_656 . ? O5 Er1 O6 136.2(2) 1_656 . ? O7 Er1 O6 53.6(2) . . ? O3 Er1 O6 105.0(2) 1_655 . ? O4 Er1 O6 141.1(2) 1_656 . ? O8 Er1 O2 86.6(2) . 1_655 ? O9 Er1 O2 153.0(2) . 1_655 ? O3 Er1 O2 118.9(2) 3_656 1_655 ? O5 Er1 O2 75.8(2) 1_656 1_655 ? O7 Er1 O2 87.1(2) . 1_655 ? O3 Er1 O2 52.2(2) 1_655 1_655 ? O4 Er1 O2 128.0(2) 1_656 1_655 ? O6 Er1 O2 70.8(2) . 1_655 ? O8 Er1 C9 78.2(3) . 1_656 ? O9 Er1 C9 99.9(3) . 1_656 ? O3 Er1 C9 79.5(3) 3_656 1_656 ? O5 Er1 C9 26.6(2) 1_656 1_656 ? O7 Er1 C9 157.0(3) . 1_656 ? O3 Er1 C9 92.1(2) 1_655 1_656 ? O4 Er1 C9 26.7(2) 1_656 1_656 ? O6 Er1 C9 149.4(3) . 1_656 ? O2 Er1 C9 102.4(2) 1_655 1_656 ? O8 Er1 C8 111.4(3) . 1_655 ? O9 Er1 C8 157.7(3) . 1_655 ? O3 Er1 C8 93.1(3) 3_656 1_655 ? O5 Er1 C8 74.9(2) 1_656 1_655 ? O7 Er1 C8 79.6(3) . 1_655 ? O3 Er1 C8 26.4(2) 1_655 1_655 ? O4 Er1 C8 125.7(2) 1_656 1_655 ? O6 Er1 C8 86.4(3) . 1_655 ? O2 Er1 C8 25.9(2) 1_655 1_655 ? C9 Er1 C8 99.7(3) 1_656 1_655 ? O1 C1 C6 123.0(9) . . ? O1 C1 C2 117.2(8) . . ? C6 C1 C2 119.7(9) . . ? C3 C2 C1 119.6(8) . . ? C3 C2 C9 118.8(9) . . ? C1 C2 C9 121.5(8) . . ? C2 C3 C4 120.8(9) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 119.0(9) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.3(9) . . ? C4 C5 C10 119.6(9) . . ? C6 C5 C10 119.0(8) . . ? C1 C6 C5 119.6(9) . . ? C1 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? O1 C7 C8 113.7(8) . . ? O1 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? O1 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? O2 C8 O3 120.8(9) . . ? O2 C8 C7 122.4(9) . . ? O3 C8 C7 116.7(9) . . ? O2 C8 Er1 62.1(5) . 1_455 ? O3 C8 Er1 59.1(5) . 1_455 ? C7 C8 Er1 169.7(6) . 1_455 ? O4 C9 O5 119.9(9) . . ? O4 C9 C2 120.9(8) . . ? O5 C9 C2 119.1(8) . . ? O4 C9 Er1 61.4(5) . 1_454 ? O5 C9 Er1 59.2(5) . 1_454 ? C2 C9 Er1 174.5(7) . 1_454 ? O7 C10 O6 120.1(8) . . ? O7 C10 C5 120.7(10) . . ? O6 C10 C5 119.2(9) . . ? C1 O1 C7 120.3(8) . . ? C8 O2 Er1 92.0(5) . 1_455 ? C8 O3 Er1 151.7(6) . 3_656 ? C8 O3 Er1 94.5(6) . 1_455 ? Er1 O3 Er1 113.3(2) 3_656 1_455 ? C9 O4 Er1 92.0(5) . 1_454 ? C9 O5 Er1 94.2(5) . 1_454 ? C10 O6 Er1 91.5(5) . . ? C10 O7 Er1 94.8(6) . . ? Er1 O8 H8A 128.5 . . ? Er1 O8 H8B 117.9 . . ? H8A O8 H8B 113.3 . . ? Er1 O9 H9A 128.3 . . ? Er1 O9 H9B 106.1 . . ? H9A O9 H9B 111.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -177.1(8) . . . . ? C6 C1 C2 C3 1.7(15) . . . . ? O1 C1 C2 C9 -1.3(14) . . . . ? C6 C1 C2 C9 177.4(9) . . . . ? C1 C2 C3 C4 -2.7(15) . . . . ? C9 C2 C3 C4 -178.6(9) . . . . ? C2 C3 C4 C5 2.1(16) . . . . ? C3 C4 C5 C6 -0.6(16) . . . . ? C3 C4 C5 C10 -177.1(9) . . . . ? O1 C1 C6 C5 178.6(9) . . . . ? C2 C1 C6 C5 -0.1(15) . . . . ? C4 C5 C6 C1 -0.5(16) . . . . ? C10 C5 C6 C1 176.1(9) . . . . ? O1 C7 C8 O2 -5.7(13) . . . . ? O1 C7 C8 O3 170.5(8) . . . . ? O1 C7 C8 Er1 107(4) . . . 1_455 ? C3 C2 C9 O4 -140.6(10) . . . . ? C1 C2 C9 O4 43.6(14) . . . . ? C3 C2 C9 O5 35.6(14) . . . . ? C1 C2 C9 O5 -140.2(10) . . . . ? C3 C2 C9 Er1 106(7) . . . 1_454 ? C1 C2 C9 Er1 -70(7) . . . 1_454 ? C4 C5 C10 O7 -142.1(10) . . . . ? C6 C5 C10 O7 41.3(14) . . . . ? C4 C5 C10 O6 39.4(14) . . . . ? C6 C5 C10 O6 -137.2(10) . . . . ? C6 C1 O1 C7 -3.6(14) . . . . ? C2 C1 O1 C7 175.2(9) . . . . ? C8 C7 O1 C1 92.3(10) . . . . ? O3 C8 O2 Er1 -6.7(9) . . . 1_455 ? C7 C8 O2 Er1 169.3(8) . . . 1_455 ? O2 C8 O3 Er1 176.4(8) . . . 3_656 ? C7 C8 O3 Er1 0.2(18) . . . 3_656 ? Er1 C8 O3 Er1 169.5(13) 1_455 . . 3_656 ? O2 C8 O3 Er1 6.9(9) . . . 1_455 ? C7 C8 O3 Er1 -169.3(7) . . . 1_455 ? O5 C9 O4 Er1 9.5(10) . . . 1_454 ? C2 C9 O4 Er1 -174.3(8) . . . 1_454 ? O4 C9 O5 Er1 -9.7(10) . . . 1_454 ? C2 C9 O5 Er1 174.0(8) . . . 1_454 ? O7 C10 O6 Er1 0.0(9) . . . . ? C5 C10 O6 Er1 178.5(7) . . . . ? O8 Er1 O6 C10 -166.2(6) . . . . ? O9 Er1 O6 C10 -80.9(5) . . . . ? O3 Er1 O6 C10 -11.1(6) 3_656 . . . ? O5 Er1 O6 C10 143.5(5) 1_656 . . . ? O7 Er1 O6 C10 0.0(5) . . . . ? O3 Er1 O6 C10 60.9(6) 1_655 . . . ? O4 Er1 O6 C10 -131.6(5) 1_656 . . . ? O2 Er1 O6 C10 101.0(5) 1_655 . . . ? C9 Er1 O6 C10 -177.2(6) 1_656 . . . ? C8 Er1 O6 C10 79.8(6) 1_655 . . . ? O6 C10 O7 Er1 0.0(9) . . . . ? C5 C10 O7 Er1 -178.5(7) . . . . ? O8 Er1 O7 C10 15.8(7) . . . . ? O9 Er1 O7 C10 89.1(6) . . . . ? O3 Er1 O7 C10 171.3(6) 3_656 . . . ? O5 Er1 O7 C10 -121.4(6) 1_656 . . . ? O3 Er1 O7 C10 -120.0(6) 1_655 . . . ? O4 Er1 O7 C10 128.9(6) 1_656 . . . ? O6 Er1 O7 C10 0.0(5) . . . . ? O2 Er1 O7 C10 -68.2(6) 1_655 . . . ? C9 Er1 O7 C10 176.4(7) 1_656 . . . ? C8 Er1 O7 C10 -93.2(6) 1_655 . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.990 _refine_diff_density_min -0.999 _refine_diff_density_rms 0.192 data_3 _database_code_depnum_ccdc_archive 'CCDC 906610' #TrackingRef '906610.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Eu O10' _chemical_formula_weight 443.15 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' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.96312(18) _cell_length_b 15.7701(3) _cell_length_c 8.95189(18) _cell_angle_alpha 90.00 _cell_angle_beta 100.376(2) _cell_angle_gamma 90.00 _cell_volume 1244.65(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1085 _cell_measurement_theta_min 2.5105 _cell_measurement_theta_max 28.7933 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 5.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5155 _exptl_absorpt_correction_T_max 0.6299 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number 3908 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7253 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2162 _reflns_number_gt 1876 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _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^+0.0000P] 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 2162 _refine_ls_number_parameters 199 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0210 _refine_ls_wR_factor_ref 0.0467 _refine_ls_wR_factor_gt 0.0452 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.039 _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 1.048901(19) 0.872764(11) 1.007180(19) 0.00815(8) Uani 1 1 d . . . C1 C 0.6855(4) 0.9100(2) 0.4878(4) 0.0121(8) Uani 1 1 d . . . C2 C 0.6757(4) 0.8674(2) 0.6242(4) 0.0125(8) Uani 1 1 d . . . C3 C 0.5391(4) 0.8299(2) 0.6400(4) 0.0149(9) Uani 1 1 d . . . H3 H 0.5313 0.8033 0.7310 0.018 Uiso 1 1 calc R . . C4 C 0.4139(4) 0.8312(2) 0.5231(4) 0.0132(8) Uani 1 1 d . . . H4 H 0.3241 0.8043 0.5338 0.016 Uiso 1 1 calc R . . C5 C 0.4258(4) 0.8739(2) 0.3890(4) 0.0116(8) Uani 1 1 d . . . C6 C 0.5601(4) 0.9139(2) 0.3735(4) 0.0140(8) Uani 1 1 d . . . H6 H 0.5655 0.9436 0.2849 0.017 Uiso 1 1 calc R . . C7 C 0.8348(4) 1.0006(2) 0.3514(4) 0.0169(9) Uani 1 1 d . . . H7A H 0.9057 1.0463 0.3839 0.020 Uiso 1 1 calc R . . H7B H 0.7371 1.0259 0.3112 0.020 Uiso 1 1 calc R . . C8 C 0.8891(4) 0.9509(2) 0.2255(4) 0.0129(8) Uani 1 1 d . . . C9 C 0.8053(4) 0.8614(2) 0.7542(4) 0.0109(8) Uani 1 1 d . . . C10 C 0.2946(4) 0.8743(2) 0.2594(4) 0.0118(8) Uani 1 1 d . . . O1 O 0.8206(3) 0.94977(17) 0.4797(3) 0.0186(6) Uani 1 1 d . . . O2 O 0.9101(3) 0.87327(15) 0.2332(3) 0.0159(6) Uani 1 1 d . . . O3 O 0.9233(3) 0.99360(15) 0.1157(3) 0.0121(6) Uani 1 1 d . . . O4 O 0.9397(3) 0.85041(16) 0.7340(3) 0.0122(6) Uani 1 1 d . . . O5 O 0.7783(3) 0.86698(16) 0.8892(3) 0.0166(6) Uani 1 1 d . . . O6 O 0.2616(3) 0.93959(16) 0.1808(3) 0.0193(6) Uani 1 1 d . . . O7 O 0.2182(3) 0.80605(16) 0.2288(3) 0.0156(6) Uani 1 1 d . . . O8 O 1.0100(3) 0.72440(16) 0.9893(3) 0.0154(6) Uani 1 1 d . . . H8A H 0.9872 0.6954 1.0629 0.018 Uiso 1 1 d R . . H8B H 0.9733 0.7010 0.9036 0.018 Uiso 1 1 d R . . O9 O 1.2557(3) 0.84163(17) 0.8851(3) 0.0170(6) Uani 1 1 d . . . H9A H 1.2525 0.7930 0.8446 0.020 Uiso 1 1 d R . . H9B H 1.3465 0.8567 0.9188 0.020 Uiso 1 1 d R . . O10 O 0.5399(8) 0.8872(5) 1.0129(7) 0.0300(17) Uani 0.50 1 d PU . . O10' O 0.5174(8) 0.9308(5) 0.9696(8) 0.0284(17) Uani 0.50 1 d PU . . 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 0.00819(11) 0.01009(11) 0.00587(11) 0.00015(7) 0.00040(8) -0.00027(8) C1 0.011(2) 0.0134(19) 0.0122(19) -0.0023(15) 0.0030(16) -0.0008(16) C2 0.0105(19) 0.0119(19) 0.0142(19) -0.0040(16) -0.0005(16) 0.0036(16) C3 0.020(2) 0.016(2) 0.0081(19) 0.0035(16) 0.0017(17) -0.0033(17) C4 0.0083(19) 0.020(2) 0.0120(19) 0.0001(16) 0.0027(16) -0.0053(16) C5 0.0106(19) 0.0131(19) 0.0098(18) -0.0015(16) -0.0020(16) -0.0004(16) C6 0.017(2) 0.020(2) 0.0050(18) 0.0024(16) 0.0017(17) -0.0008(17) C7 0.017(2) 0.020(2) 0.0131(19) 0.0042(16) 0.0007(17) -0.0029(18) C8 0.0092(19) 0.017(2) 0.0125(19) 0.0021(17) 0.0027(16) -0.0003(16) C9 0.0102(19) 0.011(2) 0.0097(19) -0.0001(15) -0.0020(16) -0.0022(15) C10 0.0087(18) 0.020(2) 0.0069(18) -0.0011(17) 0.0026(15) 0.0029(17) O1 0.0132(15) 0.0286(16) 0.0134(13) 0.0029(12) 0.0009(12) -0.0051(12) O2 0.0247(15) 0.0111(14) 0.0128(13) 0.0017(11) 0.0055(12) 0.0028(12) O3 0.0172(14) 0.0133(14) 0.0068(12) 0.0029(10) 0.0047(11) -0.0012(11) O4 0.0103(14) 0.0190(14) 0.0069(13) -0.0035(11) 0.0006(11) -0.0009(11) O5 0.0128(14) 0.0292(16) 0.0078(13) -0.0025(11) 0.0016(11) -0.0008(12) O6 0.0233(16) 0.0156(15) 0.0151(14) 0.0023(12) -0.0067(13) -0.0022(12) O7 0.0138(14) 0.0155(15) 0.0147(14) 0.0026(11) -0.0051(12) -0.0057(12) O8 0.0246(15) 0.0141(14) 0.0067(12) 0.0015(10) 0.0009(11) -0.0048(12) O9 0.0109(14) 0.0193(14) 0.0212(15) -0.0025(12) 0.0042(12) 0.0003(12) O10 0.023(3) 0.039(3) 0.028(3) -0.010(3) 0.003(3) -0.005(3) O10' 0.021(3) 0.032(3) 0.035(3) -0.004(3) 0.014(3) -0.002(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 O9 2.367(3) . ? Eu1 O8 2.367(3) . ? Eu1 O3 2.411(2) 3_776 ? Eu1 O5 2.467(3) . ? Eu1 O6 2.469(3) 1_656 ? Eu1 O4 2.490(2) . ? Eu1 O3 2.497(2) 1_556 ? Eu1 O7 2.502(2) 1_656 ? Eu1 O2 2.559(3) 1_556 ? Eu1 C10 2.856(4) 1_656 ? Eu1 C8 2.898(4) 1_556 ? Eu1 Eu1 4.1048(4) 3_777 ? C1 O1 1.377(4) . ? C1 C6 1.379(5) . ? C1 C2 1.410(5) . ? C2 C3 1.390(5) . ? C2 C9 1.492(5) . ? C3 C4 1.390(5) . ? C4 C5 1.397(5) . ? C5 C6 1.387(5) . ? C5 C10 1.496(5) . ? C7 O1 1.424(4) . ? C7 C8 1.523(5) . ? C8 O2 1.239(4) . ? C8 O3 1.273(4) . ? C8 Eu1 2.898(4) 1_554 ? C9 O4 1.262(5) . ? C9 O5 1.277(4) . ? C10 O6 1.252(4) . ? C10 O7 1.278(4) . ? C10 Eu1 2.856(4) 1_454 ? O2 Eu1 2.559(3) 1_554 ? O3 Eu1 2.411(2) 3_776 ? O3 Eu1 2.497(2) 1_554 ? O6 Eu1 2.469(2) 1_454 ? O7 Eu1 2.502(2) 1_454 ? O10 O10' 0.797(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 Eu1 O8 83.20(9) . . ? O9 Eu1 O3 79.44(9) . 3_776 ? O8 Eu1 O3 149.25(8) . 3_776 ? O9 Eu1 O5 125.88(9) . . ? O8 Eu1 O5 79.22(9) . . ? O3 Eu1 O5 90.66(8) 3_776 . ? O9 Eu1 O6 78.41(9) . 1_656 ? O8 Eu1 O6 123.52(9) . 1_656 ? O3 Eu1 O6 77.44(8) 3_776 1_656 ? O5 Eu1 O6 150.90(9) . 1_656 ? O9 Eu1 O4 73.68(8) . . ? O8 Eu1 O4 76.49(8) . . ? O3 Eu1 O4 74.36(8) 3_776 . ? O5 Eu1 O4 52.55(8) . . ? O6 Eu1 O4 143.25(9) 1_656 . ? O9 Eu1 O3 141.58(9) . 1_556 ? O8 Eu1 O3 135.19(9) . 1_556 ? O3 Eu1 O3 66.51(10) 3_776 1_556 ? O5 Eu1 O3 73.58(8) . 1_556 ? O6 Eu1 O3 77.32(8) 1_656 1_556 ? O4 Eu1 O3 111.41(8) . 1_556 ? O9 Eu1 O7 82.25(9) . 1_656 ? O8 Eu1 O7 72.47(8) . 1_656 ? O3 Eu1 O7 129.16(8) 3_776 1_656 ? O5 Eu1 O7 137.16(8) . 1_656 ? O6 Eu1 O7 52.48(8) 1_656 1_656 ? O4 Eu1 O7 142.56(8) . 1_656 ? O3 Eu1 O7 105.31(8) 1_556 1_656 ? O9 Eu1 O2 153.97(9) . 1_556 ? O8 Eu1 O2 88.28(8) . 1_556 ? O3 Eu1 O2 117.58(8) 3_776 1_556 ? O5 Eu1 O2 76.00(8) . 1_556 ? O6 Eu1 O2 86.05(9) 1_656 1_556 ? O4 Eu1 O2 128.01(9) . 1_556 ? O3 Eu1 O2 51.14(8) 1_556 1_556 ? O7 Eu1 O2 71.72(9) 1_656 1_556 ? O9 Eu1 C10 79.07(10) . 1_656 ? O8 Eu1 C10 98.34(10) . 1_656 ? O3 Eu1 C10 103.00(10) 3_776 1_656 ? O5 Eu1 C10 153.84(10) . 1_656 ? O6 Eu1 C10 25.91(9) 1_656 1_656 ? O4 Eu1 C10 152.66(10) . 1_656 ? O3 Eu1 C10 91.35(9) 1_556 1_656 ? O7 Eu1 C10 26.56(9) 1_656 1_656 ? O2 Eu1 C10 77.91(10) 1_556 1_656 ? O9 Eu1 C8 157.36(10) . 1_556 ? O8 Eu1 C8 112.43(10) . 1_556 ? O3 Eu1 C8 92.30(10) 3_776 1_556 ? O5 Eu1 C8 74.77(9) . 1_556 ? O6 Eu1 C8 79.23(10) 1_656 1_556 ? O4 Eu1 C8 124.61(9) . 1_556 ? O3 Eu1 C8 25.96(9) 1_556 1_556 ? O7 Eu1 C8 86.97(9) 1_656 1_556 ? O2 Eu1 C8 25.28(9) 1_556 1_556 ? C10 Eu1 C8 82.39(10) 1_656 1_556 ? O9 Eu1 Eu1 111.65(6) . 3_777 ? O8 Eu1 Eu1 159.45(7) . 3_777 ? O3 Eu1 Eu1 33.92(6) 3_776 3_777 ? O5 Eu1 Eu1 80.49(6) . 3_777 ? O6 Eu1 Eu1 74.85(6) 1_656 3_777 ? O4 Eu1 Eu1 93.66(6) . 3_777 ? O3 Eu1 Eu1 32.59(6) 1_556 3_777 ? O7 Eu1 Eu1 122.11(6) 1_656 3_777 ? O2 Eu1 Eu1 83.70(5) 1_556 3_777 ? C10 Eu1 Eu1 98.42(8) 1_656 3_777 ? C8 Eu1 Eu1 58.44(7) 1_556 3_777 ? O1 C1 C6 123.2(3) . . ? O1 C1 C2 117.1(3) . . ? C6 C1 C2 119.6(4) . . ? C3 C2 C1 119.0(3) . . ? C3 C2 C9 118.0(3) . . ? C1 C2 C9 122.9(3) . . ? C2 C3 C4 121.5(3) . . ? C3 C4 C5 118.5(3) . . ? C6 C5 C4 120.5(3) . . ? C6 C5 C10 119.7(3) . . ? C4 C5 C10 119.8(3) . . ? C1 C6 C5 120.8(3) . . ? O1 C7 C8 113.2(3) . . ? O2 C8 O3 120.7(3) . . ? O2 C8 C7 122.2(3) . . ? O3 C8 C7 117.0(3) . . ? O2 C8 Eu1 61.9(2) . 1_554 ? O3 C8 Eu1 59.17(19) . 1_554 ? C7 C8 Eu1 168.7(3) . 1_554 ? O4 C9 O5 119.5(3) . . ? O4 C9 C2 121.8(3) . . ? O5 C9 C2 118.7(3) . . ? O6 C10 O7 120.6(3) . . ? O6 C10 C5 120.8(3) . . ? O7 C10 C5 118.6(3) . . ? O6 C10 Eu1 59.50(18) . 1_454 ? O7 C10 Eu1 61.09(17) . 1_454 ? C5 C10 Eu1 178.5(3) . 1_454 ? C1 O1 C7 120.4(3) . . ? C8 O2 Eu1 92.8(2) . 1_554 ? C8 O3 Eu1 150.8(2) . 3_776 ? C8 O3 Eu1 94.9(2) . 1_554 ? Eu1 O3 Eu1 113.49(10) 3_776 1_554 ? C9 O4 Eu1 93.2(2) . . ? C9 O5 Eu1 93.9(2) . . ? C10 O6 Eu1 94.6(2) . 1_454 ? C10 O7 Eu1 92.3(2) . 1_454 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 176.9(3) . . . . ? C6 C1 C2 C3 0.1(6) . . . . ? O1 C1 C2 C9 -2.3(5) . . . . ? C6 C1 C2 C9 -179.1(3) . . . . ? C1 C2 C3 C4 2.0(6) . . . . ? C9 C2 C3 C4 -178.7(3) . . . . ? C2 C3 C4 C5 -2.2(6) . . . . ? C3 C4 C5 C6 0.1(6) . . . . ? C3 C4 C5 C10 178.2(3) . . . . ? O1 C1 C6 C5 -178.7(3) . . . . ? C2 C1 C6 C5 -2.1(6) . . . . ? C4 C5 C6 C1 2.0(6) . . . . ? C10 C5 C6 C1 -176.0(3) . . . . ? O1 C7 C8 O2 3.7(5) . . . . ? O1 C7 C8 O3 -171.2(3) . . . . ? O1 C7 C8 Eu1 -104.3(13) . . . 1_554 ? C3 C2 C9 O4 141.8(4) . . . . ? C1 C2 C9 O4 -39.0(5) . . . . ? C3 C2 C9 O5 -37.6(5) . . . . ? C1 C2 C9 O5 141.6(4) . . . . ? C6 C5 C10 O6 -41.1(5) . . . . ? C4 C5 C10 O6 140.8(4) . . . . ? C6 C5 C10 O7 137.7(4) . . . . ? C4 C5 C10 O7 -40.4(5) . . . . ? C6 C5 C10 Eu1 59(11) . . . 1_454 ? C4 C5 C10 Eu1 -119(10) . . . 1_454 ? C6 C1 O1 C7 2.4(5) . . . . ? C2 C1 O1 C7 -174.2(3) . . . . ? C8 C7 O1 C1 -90.5(4) . . . . ? O3 C8 O2 Eu1 6.9(4) . . . 1_554 ? C7 C8 O2 Eu1 -167.8(3) . . . 1_554 ? O2 C8 O3 Eu1 -173.9(3) . . . 3_776 ? C7 C8 O3 Eu1 1.1(7) . . . 3_776 ? Eu1 C8 O3 Eu1 -166.8(5) 1_554 . . 3_776 ? O2 C8 O3 Eu1 -7.1(4) . . . 1_554 ? C7 C8 O3 Eu1 167.9(3) . . . 1_554 ? O5 C9 O4 Eu1 -8.7(3) . . . . ? C2 C9 O4 Eu1 172.0(3) . . . . ? O9 Eu1 O4 C9 178.3(2) . . . . ? O8 Eu1 O4 C9 91.6(2) . . . . ? O3 Eu1 O4 C9 -98.4(2) 3_776 . . . ? O5 Eu1 O4 C9 4.90(19) . . . . ? O6 Eu1 O4 C9 -139.6(2) 1_656 . . . ? O3 Eu1 O4 C9 -42.0(2) 1_556 . . . ? O7 Eu1 O4 C9 126.2(2) 1_656 . . . ? O2 Eu1 O4 C9 14.7(2) 1_556 . . . ? C10 Eu1 O4 C9 173.5(2) 1_656 . . . ? C8 Eu1 O4 C9 -16.6(2) 1_556 . . . ? Eu1 Eu1 O4 C9 -70.2(2) 3_777 . . . ? O4 C9 O5 Eu1 8.7(3) . . . . ? C2 C9 O5 Eu1 -171.9(3) . . . . ? O9 Eu1 O5 C9 -12.6(2) . . . . ? O8 Eu1 O5 C9 -86.0(2) . . . . ? O3 Eu1 O5 C9 64.8(2) 3_776 . . . ? O6 Eu1 O5 C9 129.5(2) 1_656 . . . ? O4 Eu1 O5 C9 -4.84(19) . . . . ? O3 Eu1 O5 C9 130.0(2) 1_556 . . . ? O7 Eu1 O5 C9 -135.0(2) 1_656 . . . ? O2 Eu1 O5 C9 -176.9(2) 1_556 . . . ? C10 Eu1 O5 C9 -173.0(2) 1_656 . . . ? C8 Eu1 O5 C9 157.0(2) 1_556 . . . ? Eu1 Eu1 O5 C9 97.3(2) 3_777 . . . ? O7 C10 O6 Eu1 -0.5(4) . . . 1_454 ? C5 C10 O6 Eu1 178.3(3) . . . 1_454 ? O6 C10 O7 Eu1 0.5(4) . . . 1_454 ? C5 C10 O7 Eu1 -178.3(3) . . . 1_454 ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.979 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.113 data_4 _database_code_depnum_ccdc_archive 'CCDC 906611' #TrackingRef '906611.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Gd O10' _chemical_formula_weight 448.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/C loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9811(3) _cell_length_b 15.7995(6) _cell_length_c 8.9343(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.505(3) _cell_angle_gamma 90.00 _cell_volume 1246.50(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1085 _cell_measurement_theta_min 2.5105 _cell_measurement_theta_max 28.7933 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 5.374 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8208 _exptl_absorpt_correction_T_max 0.9042 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number 3908 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8028 _diffrn_reflns_av_R_equivalents 0.0385 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2206 _reflns_number_gt 1877 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _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^)+(0.0200P)^2^+1.3523P] 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 2206 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0569 _refine_ls_wR_factor_gt 0.0518 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 Gd1 Gd 0.54886(2) 0.126745(16) 1.00601(2) 0.01273(9) Uani 1 1 d . . . C1 C 0.1852(5) 0.0895(3) 0.4858(5) 0.0162(11) Uani 1 1 d . . . C2 C 0.1760(5) 0.1330(3) 0.6218(5) 0.0161(11) Uani 1 1 d . . . C3 C 0.0409(5) 0.1706(3) 0.6381(5) 0.0195(12) Uani 1 1 d . . . H3 H 0.0338 0.1976 0.7290 0.023 Uiso 1 1 calc R . . C4 C -0.0847(6) 0.1690(4) 0.5213(5) 0.0218(12) Uani 1 1 d . . . H4 H -0.1741 0.1959 0.5325 0.026 Uiso 1 1 calc R . . C5 C -0.0741(5) 0.1263(3) 0.3872(5) 0.0151(11) Uani 1 1 d . . . C6 C 0.0600(5) 0.0864(3) 0.3714(5) 0.0172(11) Uani 1 1 d . . . H6 H 0.0652 0.0571 0.2822 0.021 Uiso 1 1 calc R . . C7 C 0.3340(5) 0.0004(3) 0.3502(5) 0.0172(11) Uani 1 1 d . . . H7A H 0.2359 -0.0237 0.3084 0.021 Uiso 1 1 calc R . . H7B H 0.4030 -0.0459 0.3833 0.021 Uiso 1 1 calc R . . C8 C 0.3916(5) 0.0497(3) 0.2256(5) 0.0145(11) Uani 1 1 d . . . C9 C 0.3074(5) 0.1379(3) 0.7526(5) 0.0153(11) Uani 1 1 d . . . C10 C -0.2072(5) 0.1258(3) 0.2574(5) 0.0179(11) Uani 1 1 d . . . O1 O 0.3203(4) 0.0513(2) 0.4782(3) 0.0214(8) Uani 1 1 d . . . O2 O 0.4110(4) 0.1267(2) 0.2318(4) 0.0220(8) Uani 1 1 d . . . O3 O 0.4236(3) 0.0061(2) 0.1161(3) 0.0161(7) Uani 1 1 d . . . O4 O 0.4413(4) 0.1497(2) 0.7332(3) 0.0199(8) Uani 1 1 d . . . O5 O 0.2805(4) 0.1319(2) 0.8864(3) 0.0240(9) Uani 1 1 d . . . O6 O -0.2823(4) 0.1938(2) 0.2270(4) 0.0234(8) Uani 1 1 d . . . O7 O -0.2387(4) 0.0607(2) 0.1796(4) 0.0263(9) Uani 1 1 d . . . O8 O 0.7547(4) 0.1579(2) 0.8845(4) 0.0241(8) Uani 1 1 d . . . H8A H 0.8444 0.1405 0.9157 0.029 Uiso 1 1 d R . . H8B H 0.7541 0.2062 0.8434 0.029 Uiso 1 1 d R . . O9 O 0.5081(4) 0.2740(2) 0.9880(3) 0.0223(8) Uani 1 1 d . . . H9A H 0.4869 0.3002 1.0628 0.027 Uiso 1 1 d R . . H9B H 0.4680 0.2981 0.9045 0.027 Uiso 1 1 d R . . O10 O 0.0379(14) 0.3901(8) 0.5092(13) 0.042(3) Uani 0.50 1 d P . . O10' O 0.0202(17) 0.4309(8) 0.4635(15) 0.047(4) Uani 0.50 1 d P . . 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 Gd1 0.01190(14) 0.01549(16) 0.00991(14) -0.00057(10) -0.00038(9) 0.00020(10) C1 0.017(3) 0.020(3) 0.012(2) 0.005(2) 0.004(2) 0.002(2) C2 0.013(2) 0.024(3) 0.009(2) 0.000(2) -0.0021(19) -0.002(2) C3 0.020(3) 0.026(3) 0.011(2) -0.005(2) -0.002(2) 0.008(2) C4 0.018(3) 0.028(3) 0.019(3) -0.001(2) 0.003(2) 0.007(2) C5 0.014(2) 0.018(3) 0.011(2) 0.000(2) -0.0034(19) -0.001(2) C6 0.018(3) 0.019(3) 0.014(2) -0.002(2) 0.004(2) 0.004(2) C7 0.018(3) 0.021(3) 0.013(2) -0.002(2) 0.0052(19) 0.002(2) C8 0.008(2) 0.023(3) 0.012(2) -0.003(2) -0.0013(19) 0.004(2) C9 0.014(3) 0.020(3) 0.010(2) -0.002(2) -0.0047(19) 0.005(2) C10 0.015(3) 0.027(3) 0.012(2) -0.001(2) 0.003(2) -0.001(2) O1 0.0152(18) 0.033(2) 0.0163(17) -0.0075(16) 0.0035(14) 0.0041(16) O2 0.033(2) 0.016(2) 0.0174(18) -0.0052(16) 0.0069(15) -0.0043(17) O3 0.0195(18) 0.019(2) 0.0107(16) -0.0035(14) 0.0042(13) -0.0003(15) O4 0.0126(18) 0.031(2) 0.0153(17) 0.0016(16) 0.0004(14) -0.0008(16) O5 0.0141(18) 0.046(3) 0.0113(17) 0.0012(16) -0.0004(14) -0.0012(17) O6 0.0205(19) 0.024(2) 0.0219(19) -0.0025(16) -0.0061(15) 0.0066(17) O7 0.028(2) 0.021(2) 0.0244(19) -0.0059(17) -0.0103(16) 0.0004(17) O8 0.0175(18) 0.026(2) 0.028(2) 0.0029(17) 0.0031(15) -0.0013(16) O9 0.038(2) 0.017(2) 0.0107(16) -0.0007(14) 0.0011(14) 0.0088(17) O10 0.019(5) 0.082(11) 0.028(6) -0.016(6) 0.014(5) -0.013(7) O10' 0.045(7) 0.044(8) 0.057(9) 0.002(6) 0.022(6) -0.015(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Gd1 O9 2.356(4) . ? Gd1 O8 2.361(3) . ? Gd1 O3 2.399(3) 3_656 ? Gd1 O5 2.453(3) . ? Gd1 O7 2.461(3) 1_656 ? Gd1 O4 2.479(3) . ? Gd1 O6 2.495(3) 1_656 ? Gd1 O3 2.504(3) 1_556 ? Gd1 O2 2.552(3) 1_556 ? Gd1 C10 2.837(5) 1_656 ? Gd1 C9 2.840(4) . ? Gd1 C8 2.887(5) 1_556 ? C1 O1 1.368(5) . ? C1 C6 1.375(6) . ? C1 C2 1.412(6) . ? C2 C3 1.383(6) . ? C2 C9 1.504(6) . ? C3 C4 1.390(6) . ? C3 H3 0.9300 . ? C4 C5 1.393(7) . ? C4 H4 0.9300 . ? C5 C6 1.389(6) . ? C5 C10 1.506(6) . ? C6 H6 0.9300 . ? C7 O1 1.421(5) . ? C7 C8 1.524(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O2 1.229(6) . ? C8 O3 1.272(5) . ? C8 Gd1 2.887(5) 1_554 ? C9 O4 1.259(5) . ? C9 O5 1.265(5) . ? C10 O7 1.244(6) . ? C10 O6 1.272(6) . ? C10 Gd1 2.837(5) 1_454 ? O2 Gd1 2.552(3) 1_554 ? O3 Gd1 2.399(3) 3_656 ? O3 Gd1 2.504(3) 1_554 ? O6 Gd1 2.495(3) 1_454 ? O7 Gd1 2.461(3) 1_454 ? O8 H8A 0.8482 . ? O8 H8B 0.8461 . ? O9 H9A 0.8371 . ? O9 H9B 0.8569 . ? O10 O10' 0.764(13) . ? 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 O9 Gd1 O8 83.53(12) . . ? O9 Gd1 O3 149.37(10) . 3_656 ? O8 Gd1 O3 79.58(11) . 3_656 ? O9 Gd1 O5 79.03(12) . . ? O8 Gd1 O5 125.63(11) . . ? O3 Gd1 O5 90.30(11) 3_656 . ? O9 Gd1 O7 123.69(12) . 1_656 ? O8 Gd1 O7 78.24(12) . 1_656 ? O3 Gd1 O7 77.49(11) 3_656 1_656 ? O5 Gd1 O7 151.13(12) . 1_656 ? O9 Gd1 O4 76.14(11) . . ? O8 Gd1 O4 73.43(11) . . ? O3 Gd1 O4 74.63(11) 3_656 . ? O5 Gd1 O4 52.49(10) . . ? O7 Gd1 O4 143.14(11) 1_656 . ? O9 Gd1 O6 72.50(11) . 1_656 ? O8 Gd1 O6 82.04(11) . 1_656 ? O3 Gd1 O6 129.27(11) 3_656 1_656 ? O5 Gd1 O6 137.53(11) . 1_656 ? O7 Gd1 O6 52.54(12) 1_656 1_656 ? O4 Gd1 O6 141.94(12) . 1_656 ? O9 Gd1 O3 134.69(11) . 1_556 ? O8 Gd1 O3 141.74(12) . 1_556 ? O3 Gd1 O3 66.65(11) 3_656 1_556 ? O5 Gd1 O3 73.75(11) . 1_556 ? O7 Gd1 O3 77.39(11) 1_656 1_556 ? O4 Gd1 O3 112.03(10) . 1_556 ? O6 Gd1 O3 105.30(11) 1_656 1_556 ? O9 Gd1 O2 87.85(11) . 1_556 ? O8 Gd1 O2 153.79(11) . 1_556 ? O3 Gd1 O2 117.67(11) 3_656 1_556 ? O5 Gd1 O2 76.38(11) . 1_556 ? O7 Gd1 O2 86.21(11) 1_656 1_556 ? O4 Gd1 O2 128.22(11) . 1_556 ? O6 Gd1 O2 71.76(11) 1_656 1_556 ? O3 Gd1 O2 51.09(10) 1_556 1_556 ? O9 Gd1 C10 98.47(14) . 1_656 ? O8 Gd1 C10 78.98(12) . 1_656 ? O3 Gd1 C10 103.09(13) 3_656 1_656 ? O5 Gd1 C10 154.22(12) . 1_656 ? O7 Gd1 C10 25.93(13) 1_656 1_656 ? O4 Gd1 C10 152.29(12) . 1_656 ? O6 Gd1 C10 26.61(13) 1_656 1_656 ? O3 Gd1 C10 91.27(12) 1_556 1_656 ? O2 Gd1 C10 77.88(12) 1_556 1_656 ? O9 Gd1 C9 78.33(13) . . ? O8 Gd1 C9 99.71(12) . . ? O3 Gd1 C9 79.57(12) 3_656 . ? O5 Gd1 C9 26.38(12) . . ? O7 Gd1 C9 156.96(13) 1_656 . ? O4 Gd1 C9 26.28(12) . . ? O6 Gd1 C9 150.41(13) 1_656 . ? O3 Gd1 C9 91.61(12) 1_556 . ? O2 Gd1 C9 102.71(13) 1_556 . ? C10 Gd1 C9 176.69(15) 1_656 . ? O9 Gd1 C8 111.93(12) . 1_556 ? O8 Gd1 C8 157.19(12) . 1_556 ? O3 Gd1 C8 92.52(13) 3_656 1_556 ? O5 Gd1 C8 75.31(11) . 1_556 ? O7 Gd1 C8 79.17(12) 1_656 1_556 ? O4 Gd1 C8 125.34(11) . 1_556 ? O6 Gd1 C8 86.74(12) 1_656 1_556 ? O3 Gd1 C8 26.06(12) 1_556 1_556 ? O2 Gd1 C8 25.16(12) 1_556 1_556 ? C10 Gd1 C8 82.09(13) 1_656 1_556 ? C9 Gd1 C8 99.84(13) . 1_556 ? O1 C1 C6 124.0(4) . . ? O1 C1 C2 116.7(4) . . ? C6 C1 C2 119.3(4) . . ? C3 C2 C1 119.3(4) . . ? C3 C2 C9 118.4(4) . . ? C1 C2 C9 122.3(4) . . ? C2 C3 C4 121.4(4) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 118.8(5) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C6 C5 C4 120.2(4) . . ? C6 C5 C10 120.0(4) . . ? C4 C5 C10 119.7(4) . . ? C1 C6 C5 121.0(4) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? O1 C7 C8 113.0(4) . . ? O1 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? O1 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? O2 C8 O3 121.4(4) . . ? O2 C8 C7 122.5(4) . . ? O3 C8 C7 116.1(4) . . ? O2 C8 Gd1 62.0(3) . 1_554 ? O3 C8 Gd1 59.9(2) . 1_554 ? C7 C8 Gd1 170.0(3) . 1_554 ? O4 C9 O5 119.5(4) . . ? O4 C9 C2 122.3(4) . . ? O5 C9 C2 118.2(4) . . ? O4 C9 Gd1 60.6(2) . . ? O5 C9 Gd1 59.5(2) . . ? C2 C9 Gd1 173.2(3) . . ? O7 C10 O6 121.4(4) . . ? O7 C10 C5 120.2(5) . . ? O6 C10 C5 118.4(4) . . ? O7 C10 Gd1 59.9(2) . 1_454 ? O6 C10 Gd1 61.5(2) . 1_454 ? C5 C10 Gd1 178.0(3) . 1_454 ? C1 O1 C7 119.8(4) . . ? C8 O2 Gd1 92.9(3) . 1_554 ? C8 O3 Gd1 151.7(3) . 3_656 ? C8 O3 Gd1 94.0(3) . 1_554 ? Gd1 O3 Gd1 113.35(11) 3_656 1_554 ? C9 O4 Gd1 93.1(3) . . ? C9 O5 Gd1 94.1(3) . . ? C10 O6 Gd1 91.9(3) . 1_454 ? C10 O7 Gd1 94.2(3) . 1_454 ? Gd1 O8 H8A 123.9 . . ? Gd1 O8 H8B 116.4 . . ? H8A O8 H8B 111.5 . . ? Gd1 O9 H9A 119.3 . . ? Gd1 O9 H9B 122.3 . . ? H9A O9 H9B 110.7 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.589 _refine_diff_density_min -0.528 _refine_diff_density_rms 0.131 data_7 _database_code_depnum_ccdc_archive 'CCDC 906612' #TrackingRef '906612.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Ho O10' _chemical_formula_weight 456.12 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' Ho Ho -0.2175 4.6783 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.93845(13) _cell_length_b 15.6658(2) _cell_length_c 8.88816(16) _cell_angle_alpha 90.00 _cell_angle_beta 100.6480(15) _cell_angle_gamma 90.00 _cell_volume 1223.16(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1085 _cell_measurement_theta_min 2.5105 _cell_measurement_theta_max 28.7933 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 6.523 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4843 _exptl_absorpt_correction_T_max 0.5616 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number 3908 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8965 _diffrn_reflns_av_R_equivalents 0.0291 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2165 _reflns_number_gt 1954 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _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^)+(0.0138P)^2^+2.9897P] 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 2165 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0235 _refine_ls_R_factor_gt 0.0203 _refine_ls_wR_factor_ref 0.0461 _refine_ls_wR_factor_gt 0.0445 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ho1 Ho 1.047330(19) 0.374058(12) 0.50652(2) 0.01136(7) Uani 1 1 d . . . C1 C 0.6837(4) 0.4102(3) -0.0128(5) 0.0143(9) Uani 1 1 d . . . C2 C 0.6753(4) 0.3671(3) 0.1237(5) 0.0146(9) Uani 1 1 d . . . C3 C 0.5389(5) 0.3294(3) 0.1400(5) 0.0185(10) Uani 1 1 d . . . H3 H 0.5318 0.3021 0.2313 0.022 Uiso 1 1 calc R . . C4 C 0.4126(5) 0.3317(3) 0.0223(5) 0.0198(10) Uani 1 1 d . . . H4 H 0.3220 0.3055 0.0338 0.024 Uiso 1 1 calc R . . C5 C 0.4235(5) 0.3736(3) -0.1120(5) 0.0154(9) Uani 1 1 d . . . C6 C 0.5591(5) 0.4136(3) -0.1288(5) 0.0168(9) Uani 1 1 d . . . H6 H 0.5649 0.4427 -0.2188 0.020 Uiso 1 1 calc R . . C7 C 0.8333(5) 0.4998(3) -0.1510(5) 0.0198(10) Uani 1 1 d . . . H7A H 0.9022 0.5468 -0.1179 0.024 Uiso 1 1 calc R . . H7B H 0.7344 0.5239 -0.1930 0.024 Uiso 1 1 calc R . . C8 C 0.8909(4) 0.4509(3) -0.2759(5) 0.0145(9) Uani 1 1 d . . . C9 C 0.8060(4) 0.3622(3) 0.2555(5) 0.0130(9) Uani 1 1 d . . . C10 C 0.2909(4) 0.3743(3) -0.2430(5) 0.0171(10) Uani 1 1 d . . . O1 O 0.8200(3) 0.4490(2) -0.0217(4) 0.0228(7) Uani 1 1 d . . . O2 O 0.9260(3) 0.49407(17) -0.3850(3) 0.0143(6) Uani 1 1 d . . . O3 O 0.9103(4) 0.37252(18) -0.2698(4) 0.0227(7) Uani 1 1 d . . . O4 O 0.9406(3) 0.35020(18) 0.2349(3) 0.0160(6) Uani 1 1 d . . . O5 O 0.7814(3) 0.3690(2) 0.3896(4) 0.0224(7) Uani 1 1 d . . . O6 O 0.2137(3) 0.30637(19) -0.2737(4) 0.0227(7) Uani 1 1 d . . . O7 O 0.2585(3) 0.43958(19) -0.3233(4) 0.0256(8) Uani 1 1 d . . . O8 O 1.0061(3) 0.22825(19) 0.4890(4) 0.0211(7) Uani 1 1 d . . . H8A H 0.9822 0.2015 0.5648 0.029(15) Uiso 1 1 d R . . H8B H 0.9722 0.2018 0.4064 0.042(17) Uiso 1 1 d R . . O9 O 1.2506(3) 0.3418(2) 0.3882(4) 0.0215(7) Uani 1 1 d . . . H9A H 1.2453 0.2960 0.3385 0.036(16) Uiso 1 1 d R . . H9B H 1.3405 0.3594 0.4155 0.051(19) Uiso 1 1 d R . . O10 O 0.5362(12) 0.3876(8) 0.5110(13) 0.047(3) Uani 0.50 1 d P . . O10' O 0.5186(14) 0.4317(7) 0.4669(15) 0.049(3) Uani 0.50 1 d P . . 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 Ho1 0.01055(11) 0.01446(11) 0.00835(12) 0.00042(8) -0.00019(7) -0.00036(7) C1 0.010(2) 0.020(2) 0.014(2) -0.0028(19) 0.0043(17) -0.0040(16) C2 0.012(2) 0.017(2) 0.013(2) -0.0020(19) -0.0017(17) -0.0025(17) C3 0.018(2) 0.026(2) 0.011(3) 0.005(2) 0.0012(18) -0.0050(18) C4 0.014(2) 0.030(3) 0.014(3) -0.001(2) -0.0004(18) -0.0100(19) C5 0.016(2) 0.017(2) 0.011(2) 0.0001(19) -0.0031(17) 0.0026(17) C6 0.018(2) 0.022(2) 0.009(2) 0.0033(19) 0.0000(17) -0.0049(18) C7 0.022(2) 0.023(2) 0.016(3) 0.005(2) 0.0069(19) -0.0029(19) C8 0.010(2) 0.019(2) 0.015(3) -0.0004(19) 0.0013(17) -0.0011(16) C9 0.013(2) 0.015(2) 0.010(2) -0.0001(18) -0.0013(17) -0.0024(16) C10 0.012(2) 0.025(2) 0.013(3) -0.001(2) -0.0008(17) 0.0011(18) O1 0.0160(15) 0.0362(19) 0.0161(19) 0.0074(15) 0.0028(13) -0.0068(13) O2 0.0191(15) 0.0159(15) 0.0096(17) 0.0032(13) 0.0069(12) -0.0009(12) O3 0.0365(19) 0.0177(17) 0.0159(19) 0.0043(14) 0.0100(14) 0.0025(14) O4 0.0124(15) 0.0249(16) 0.0098(17) -0.0015(13) -0.0003(12) 0.0005(12) O5 0.0133(15) 0.041(2) 0.0111(18) -0.0031(15) -0.0019(12) 0.0016(13) O6 0.0205(16) 0.0240(17) 0.020(2) 0.0034(14) -0.0063(13) -0.0065(13) O7 0.0247(17) 0.0215(17) 0.025(2) 0.0026(15) -0.0106(14) -0.0024(13) O8 0.0349(18) 0.0175(16) 0.0113(18) 0.0022(14) 0.0049(14) -0.0065(13) O9 0.0147(16) 0.0241(17) 0.026(2) -0.0059(15) 0.0057(13) -0.0004(13) O10 0.021(5) 0.093(9) 0.030(7) -0.022(6) 0.011(4) -0.021(6) O10' 0.044(6) 0.058(7) 0.052(9) -0.002(6) 0.024(5) -0.019(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ho1 O8 2.314(3) . ? Ho1 O9 2.317(3) . ? Ho1 O2 2.364(3) 3_765 ? Ho1 O5 2.413(3) . ? Ho1 O7 2.418(3) 1_656 ? Ho1 O2 2.455(3) 1_556 ? Ho1 O4 2.455(3) . ? Ho1 O6 2.466(3) 1_656 ? Ho1 O3 2.521(3) 1_556 ? Ho1 C9 2.808(4) . ? Ho1 C10 2.812(4) 1_656 ? Ho1 C8 2.854(4) 1_556 ? C1 C6 1.372(6) . ? C1 O1 1.377(5) . ? C1 C2 1.402(6) . ? C2 C3 1.386(6) . ? C2 C9 1.496(6) . ? C3 C4 1.391(6) . ? C4 C5 1.380(6) . ? C5 C6 1.397(6) . ? C5 C10 1.500(6) . ? C7 O1 1.421(5) . ? C7 C8 1.515(6) . ? C8 O3 1.240(5) . ? C8 O2 1.268(5) . ? C8 Ho1 2.854(4) 1_554 ? C9 O5 1.256(5) . ? C9 O4 1.264(5) . ? C10 O7 1.251(5) . ? C10 O6 1.270(5) . ? C10 Ho1 2.812(4) 1_454 ? O2 Ho1 2.364(3) 3_765 ? O2 Ho1 2.455(3) 1_554 ? O3 Ho1 2.521(3) 1_554 ? O6 Ho1 2.466(3) 1_454 ? O7 Ho1 2.418(3) 1_454 ? O10 O10' 0.796(12) . ? 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 O8 Ho1 O9 83.24(11) . . ? O8 Ho1 O2 149.34(11) . 3_765 ? O9 Ho1 O2 80.19(10) . 3_765 ? O8 Ho1 O5 78.88(11) . . ? O9 Ho1 O5 126.16(11) . . ? O2 Ho1 O5 90.36(10) 3_765 . ? O8 Ho1 O7 123.85(11) . 1_656 ? O9 Ho1 O7 77.86(11) . 1_656 ? O2 Ho1 O7 77.40(10) 3_765 1_656 ? O5 Ho1 O7 151.16(11) . 1_656 ? O8 Ho1 O2 134.90(10) . 1_556 ? O9 Ho1 O2 141.79(10) . 1_556 ? O2 Ho1 O2 66.38(11) 3_765 1_556 ? O5 Ho1 O2 73.90(10) . 1_556 ? O7 Ho1 O2 77.27(10) 1_656 1_556 ? O8 Ho1 O4 75.85(11) . . ? O9 Ho1 O4 73.46(10) . . ? O2 Ho1 O4 74.77(10) 3_765 . ? O5 Ho1 O4 53.04(9) . . ? O7 Ho1 O4 142.77(10) 1_656 . ? O2 Ho1 O4 112.54(9) 1_556 . ? O8 Ho1 O6 72.18(11) . 1_656 ? O9 Ho1 O6 81.78(11) . 1_656 ? O2 Ho1 O6 129.87(10) 3_765 1_656 ? O5 Ho1 O6 136.81(10) . 1_656 ? O7 Ho1 O6 53.15(10) 1_656 1_656 ? O2 Ho1 O6 105.29(10) 1_556 1_656 ? O4 Ho1 O6 141.41(10) . 1_656 ? O8 Ho1 O3 87.09(10) . 1_556 ? O9 Ho1 O3 153.12(11) . 1_556 ? O2 Ho1 O3 118.26(9) 3_765 1_556 ? O5 Ho1 O3 75.86(11) . 1_556 ? O7 Ho1 O3 87.00(11) 1_656 1_556 ? O2 Ho1 O3 51.92(9) 1_556 1_556 ? O4 Ho1 O3 128.10(10) . 1_556 ? O6 Ho1 O3 71.38(10) 1_656 1_556 ? O8 Ho1 C9 78.01(11) . . ? O9 Ho1 C9 100.17(11) . . ? O2 Ho1 C9 79.75(11) 3_765 . ? O5 Ho1 C9 26.48(11) . . ? O7 Ho1 C9 157.07(11) 1_656 . ? O2 Ho1 C9 91.86(11) 1_556 . ? O4 Ho1 C9 26.72(10) . . ? O6 Ho1 C9 149.71(11) 1_656 . ? O3 Ho1 C9 102.25(11) 1_556 . ? O8 Ho1 C10 98.31(12) . 1_656 ? O9 Ho1 C10 78.58(12) . 1_656 ? O2 Ho1 C10 103.42(11) 3_765 1_656 ? O5 Ho1 C10 153.91(12) . 1_656 ? O7 Ho1 C10 26.32(11) 1_656 1_656 ? O2 Ho1 C10 91.26(11) 1_556 1_656 ? O4 Ho1 C10 151.89(11) . 1_656 ? O6 Ho1 C10 26.83(11) 1_656 1_656 ? O3 Ho1 C10 78.10(12) 1_556 1_656 ? C9 Ho1 C10 176.26(12) . 1_656 ? O8 Ho1 C8 111.72(11) . 1_556 ? O9 Ho1 C8 157.39(11) . 1_556 ? O2 Ho1 C8 92.54(11) 3_765 1_556 ? O5 Ho1 C8 74.84(11) . 1_556 ? O7 Ho1 C8 79.67(11) 1_656 1_556 ? O2 Ho1 C8 26.29(10) 1_556 1_556 ? O4 Ho1 C8 125.49(10) . 1_556 ? O6 Ho1 C8 86.78(11) 1_656 1_556 ? O3 Ho1 C8 25.73(10) 1_556 1_556 ? C9 Ho1 C8 99.54(12) . 1_556 ? C10 Ho1 C8 82.41(12) 1_656 1_556 ? C6 C1 O1 122.9(4) . . ? C6 C1 C2 120.2(4) . . ? O1 C1 C2 116.8(4) . . ? C3 C2 C1 119.0(4) . . ? C3 C2 C9 118.1(4) . . ? C1 C2 C9 122.9(4) . . ? C2 C3 C4 121.1(4) . . ? C5 C4 C3 119.1(4) . . ? C4 C5 C6 120.5(4) . . ? C4 C5 C10 120.2(4) . . ? C6 C5 C10 119.4(4) . . ? C1 C6 C5 120.1(4) . . ? O1 C7 C8 113.6(4) . . ? O3 C8 O2 120.6(4) . . ? O3 C8 C7 122.2(4) . . ? O2 C8 C7 117.2(4) . . ? O3 C8 Ho1 61.9(2) . 1_554 ? O2 C8 Ho1 59.0(2) . 1_554 ? C7 C8 Ho1 170.1(3) . 1_554 ? O5 C9 O4 119.2(4) . . ? O5 C9 C2 119.4(4) . . ? O4 C9 C2 121.4(4) . . ? O5 C9 Ho1 58.9(2) . . ? O4 C9 Ho1 60.9(2) . . ? C2 C9 Ho1 173.2(3) . . ? O7 C10 O6 120.2(4) . . ? O7 C10 C5 121.0(4) . . ? O6 C10 C5 118.7(4) . . ? O7 C10 Ho1 59.0(2) . 1_454 ? O6 C10 Ho1 61.2(2) . 1_454 ? C5 C10 Ho1 178.6(3) . 1_454 ? C1 O1 C7 120.1(3) . . ? C8 O2 Ho1 151.1(3) . 3_765 ? C8 O2 Ho1 94.7(2) . 1_554 ? Ho1 O2 Ho1 113.62(11) 3_765 1_554 ? C8 O3 Ho1 92.3(2) . 1_554 ? C9 O4 Ho1 92.4(2) . . ? C9 O5 Ho1 94.6(2) . . ? C10 O6 Ho1 92.0(3) . 1_454 ? C10 O7 Ho1 94.7(3) . 1_454 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.9(6) . . . . ? O1 C1 C2 C3 177.9(4) . . . . ? C6 C1 C2 C9 -178.9(4) . . . . ? O1 C1 C2 C9 -0.1(6) . . . . ? C1 C2 C3 C4 1.7(7) . . . . ? C9 C2 C3 C4 179.8(4) . . . . ? C2 C3 C4 C5 -1.0(7) . . . . ? C3 C4 C5 C6 -0.6(7) . . . . ? C3 C4 C5 C10 177.7(4) . . . . ? O1 C1 C6 C5 -179.3(4) . . . . ? C2 C1 C6 C5 -0.6(7) . . . . ? C4 C5 C6 C1 1.3(7) . . . . ? C10 C5 C6 C1 -176.9(4) . . . . ? O1 C7 C8 O3 6.3(6) . . . . ? O1 C7 C8 O2 -170.4(3) . . . . ? O1 C7 C8 Ho1 -105.7(17) . . . 1_554 ? C3 C2 C9 O5 -38.0(6) . . . . ? C1 C2 C9 O5 140.0(4) . . . . ? C3 C2 C9 O4 141.0(4) . . . . ? C1 C2 C9 O4 -41.0(6) . . . . ? C3 C2 C9 Ho1 -111(2) . . . . ? C1 C2 C9 Ho1 67(3) . . . . ? O8 Ho1 C9 O5 89.1(3) . . . . ? O9 Ho1 C9 O5 169.9(2) . . . . ? O2 Ho1 C9 O5 -112.2(3) 3_765 . . . ? O7 Ho1 C9 O5 -107.3(3) 1_656 . . . ? O2 Ho1 C9 O5 -46.6(2) 1_556 . . . ? O4 Ho1 C9 O5 171.4(4) . . . . ? O6 Ho1 C9 O5 78.8(3) 1_656 . . . ? O3 Ho1 C9 O5 4.8(3) 1_556 . . . ? C10 Ho1 C9 O5 99.8(18) 1_656 . . . ? C8 Ho1 C9 O5 -21.3(3) 1_556 . . . ? O8 Ho1 C9 O4 -82.3(2) . . . . ? O9 Ho1 C9 O4 -1.5(2) . . . . ? O2 Ho1 C9 O4 76.4(2) 3_765 . . . ? O5 Ho1 C9 O4 -171.4(4) . . . . ? O7 Ho1 C9 O4 81.3(4) 1_656 . . . ? O2 Ho1 C9 O4 142.0(2) 1_556 . . . ? O6 Ho1 C9 O4 -92.6(3) 1_656 . . . ? O3 Ho1 C9 O4 -166.6(2) 1_556 . . . ? C10 Ho1 C9 O4 -71.6(18) 1_656 . . . ? C8 Ho1 C9 O4 167.3(2) 1_556 . . . ? O8 Ho1 C9 C2 166(2) . . . . ? O9 Ho1 C9 C2 -113(2) . . . . ? O2 Ho1 C9 C2 -35(2) 3_765 . . . ? O5 Ho1 C9 C2 77(2) . . . . ? O7 Ho1 C9 C2 -30(3) 1_656 . . . ? O2 Ho1 C9 C2 31(2) 1_556 . . . ? O4 Ho1 C9 C2 -111(3) . . . . ? O6 Ho1 C9 C2 156(2) 1_656 . . . ? O3 Ho1 C9 C2 82(2) 1_556 . . . ? C10 Ho1 C9 C2 177(2) 1_656 . . . ? C8 Ho1 C9 C2 56(2) 1_556 . . . ? C4 C5 C10 O7 141.1(4) . . . . ? C6 C5 C10 O7 -40.6(6) . . . . ? C4 C5 C10 O6 -40.5(6) . . . . ? C6 C5 C10 O6 137.7(4) . . . . ? C4 C5 C10 Ho1 -128(13) . . . 1_454 ? C6 C5 C10 Ho1 51(13) . . . 1_454 ? C6 C1 O1 C7 4.1(6) . . . . ? C2 C1 O1 C7 -174.7(4) . . . . ? C8 C7 O1 C1 -93.1(4) . . . . ? O3 C8 O2 Ho1 -175.8(3) . . . 3_765 ? C7 C8 O2 Ho1 0.9(8) . . . 3_765 ? Ho1 C8 O2 Ho1 -168.7(6) 1_554 . . 3_765 ? O3 C8 O2 Ho1 -7.1(4) . . . 1_554 ? C7 C8 O2 Ho1 169.6(3) . . . 1_554 ? O2 C8 O3 Ho1 6.9(4) . . . 1_554 ? C7 C8 O3 Ho1 -169.6(4) . . . 1_554 ? O5 C9 O4 Ho1 -8.4(4) . . . . ? C2 C9 O4 Ho1 172.6(3) . . . . ? O8 Ho1 O4 C9 91.4(2) . . . . ? O9 Ho1 O4 C9 178.4(2) . . . . ? O2 Ho1 O4 C9 -97.5(2) 3_765 . . . ? O5 Ho1 O4 C9 4.8(2) . . . . ? O7 Ho1 O4 C9 -140.5(2) 1_656 . . . ? O2 Ho1 O4 C9 -41.7(2) 1_556 . . . ? O6 Ho1 O4 C9 126.1(2) 1_656 . . . ? O3 Ho1 O4 C9 16.7(3) 1_556 . . . ? C10 Ho1 O4 C9 172.4(3) 1_656 . . . ? C8 Ho1 O4 C9 -15.4(3) 1_556 . . . ? O4 C9 O5 Ho1 8.6(4) . . . . ? C2 C9 O5 Ho1 -172.4(3) . . . . ? O8 Ho1 O5 C9 -85.4(3) . . . . ? O9 Ho1 O5 C9 -12.4(3) . . . . ? O2 Ho1 O5 C9 65.7(3) 3_765 . . . ? O7 Ho1 O5 C9 129.5(3) 1_656 . . . ? O2 Ho1 O5 C9 130.9(3) 1_556 . . . ? O4 Ho1 O5 C9 -4.8(2) . . . . ? O6 Ho1 O5 C9 -133.7(2) 1_656 . . . ? O3 Ho1 O5 C9 -175.2(3) 1_556 . . . ? C10 Ho1 O5 C9 -171.6(3) 1_656 . . . ? C8 Ho1 O5 C9 158.2(3) 1_556 . . . ? O7 C10 O6 Ho1 0.0(4) . . . 1_454 ? C5 C10 O6 Ho1 -178.4(3) . . . 1_454 ? O6 C10 O7 Ho1 0.0(4) . . . 1_454 ? C5 C10 O7 Ho1 178.3(4) . . . 1_454 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.816 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.111 data_10 _database_code_depnum_ccdc_archive 'CCDC 906613' #TrackingRef '906613.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Lu O10' _chemical_formula_weight 466.16 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' Lu Lu -0.4720 5.8584 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9151(18) _cell_length_b 15.521(3) _cell_length_c 8.8732(18) _cell_angle_alpha 90.00 _cell_angle_beta 100.58(3) _cell_angle_gamma 90.00 _cell_volume 1206.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1085 _cell_measurement_theta_min 2.5105 _cell_measurement_theta_max 28.7933 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 8.235 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4931 _exptl_absorpt_correction_T_max 0.6836 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number 3908 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6745 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0470 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2102 _reflns_number_gt 1741 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _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^)+(0.0147P)^2^+7.3175P] 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 SHELXL _refine_ls_extinction_coef 0.00053(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2102 _refine_ls_number_parameters 200 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.0710 _refine_ls_wR_factor_gt 0.0671 _refine_ls_goodness_of_fit_ref 1.236 _refine_ls_restrained_S_all 1.235 _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 Lu1 Lu 0.45395(4) 0.87500(3) -0.00593(4) 0.01527(14) Uani 1 1 d . . . C1 C 0.8165(9) 0.9096(5) 0.5128(9) 0.0143(19) Uani 1 1 d . . . C2 C 0.8250(9) 0.8676(6) 0.3756(9) 0.0161(18) Uani 1 1 d . . . C3 C 0.9636(9) 0.8293(6) 0.3606(9) 0.019(2) Uani 1 1 d . . . H3 H 0.9713 0.8016 0.2694 0.022 Uiso 1 1 calc R . . C4 C 1.0887(9) 0.8316(6) 0.4771(9) 0.018(2) Uani 1 1 d . . . H4 H 1.1794 0.8053 0.4647 0.021 Uiso 1 1 calc R . . C5 C 1.0791(8) 0.8727(6) 0.6112(8) 0.0125(17) Uani 1 1 d . . . C6 C 0.9454(10) 0.9134(6) 0.6299(9) 0.017(2) Uani 1 1 d . . . H6 H 0.9412 0.9433 0.7200 0.021 Uiso 1 1 calc R . . C7 C 0.6681(10) 0.9996(6) 0.6522(9) 0.0167(19) Uani 1 1 d . . . H7A H 0.6007 1.0478 0.6196 0.020 Uiso 1 1 calc R . . H7B H 0.7680 1.0228 0.6945 0.020 Uiso 1 1 calc R . . C8 C 0.6086(9) 0.9508(6) 0.7772(9) 0.0142(19) Uani 1 1 d . . . C9 C 0.6937(9) 0.8618(6) 0.2440(9) 0.0149(19) Uani 1 1 d . . . C10 C 1.2128(9) 0.8739(7) 0.7428(9) 0.0188(19) Uani 1 1 d . . . O1 O 0.6797(6) 0.9484(4) 0.5225(6) 0.0207(14) Uani 1 1 d . . . O2 O 0.5895(7) 0.8713(4) 0.7719(6) 0.0238(14) Uani 1 1 d . . . O3 O 0.5719(6) 0.9942(4) 0.8848(6) 0.0117(12) Uani 1 1 d U . . O4 O 0.7172(6) 0.8706(5) 0.1085(6) 0.0245(14) Uani 1 1 d . . . O5 O 0.5584(6) 0.8502(4) 0.2642(6) 0.0169(14) Uani 1 1 d . . . O6 O 1.2910(7) 0.8061(4) 0.7735(7) 0.0234(15) Uani 1 1 d . . . O7 O 1.2449(7) 0.9393(4) 0.8254(7) 0.0255(15) Uani 1 1 d . . . O8 O 0.2537(6) 0.8434(4) 0.1085(7) 0.0231(15) Uani 1 1 d . . . H8A H 0.1598 0.8549 0.0780 0.028 Uiso 1 1 d R . . H8B H 0.2649 0.7921 0.1420 0.028 Uiso 1 1 d R . . O9 O 0.4956(6) 0.7313(4) 0.0107(6) 0.0201(14) Uani 1 1 d . . . H9A H 0.5130 0.7058 -0.0698 0.024 Uiso 1 1 d R . . H9B H 0.5254 0.7052 0.0959 0.024 Uiso 1 1 d R . . O10 O 0.986(2) 0.5691(12) 0.530(3) 0.039(5) Uani 0.50 1 d P . . O10' O 0.958(2) 0.6144(14) 0.489(2) 0.045(5) Uani 0.50 1 d P . . 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 Lu1 0.0145(2) 0.0167(2) 0.0141(2) -0.0003(2) 0.00155(13) 0.00037(19) C1 0.016(4) 0.014(4) 0.015(4) 0.003(4) 0.006(4) -0.003(4) C2 0.018(4) 0.019(5) 0.010(4) 0.002(4) -0.002(3) 0.004(4) C3 0.020(5) 0.029(6) 0.007(4) -0.006(4) 0.001(4) 0.006(4) C4 0.011(4) 0.027(5) 0.014(5) -0.004(4) -0.001(4) 0.010(4) C5 0.012(4) 0.016(4) 0.008(4) 0.001(5) -0.004(3) -0.005(4) C6 0.026(5) 0.016(5) 0.009(4) -0.006(4) 0.001(4) 0.000(4) C7 0.016(4) 0.019(5) 0.015(4) -0.004(4) 0.002(4) 0.003(4) C8 0.013(4) 0.015(5) 0.013(4) -0.001(4) -0.002(4) 0.003(4) C9 0.011(4) 0.012(5) 0.020(5) 0.000(4) -0.001(3) 0.005(4) C10 0.014(4) 0.031(5) 0.010(4) -0.002(5) -0.001(3) -0.008(5) O1 0.011(3) 0.036(4) 0.016(3) -0.008(3) 0.005(3) 0.005(3) O2 0.039(4) 0.016(3) 0.016(3) -0.005(3) 0.005(3) -0.009(4) O3 0.0121(15) 0.0123(15) 0.0109(15) 0.0000(10) 0.0026(10) 0.0003(9) O4 0.016(3) 0.041(4) 0.015(3) -0.002(4) 0.000(2) -0.006(3) O5 0.014(3) 0.021(4) 0.015(3) -0.003(3) 0.001(2) -0.005(2) O6 0.025(3) 0.021(4) 0.021(3) -0.003(3) -0.004(3) 0.012(3) O7 0.021(3) 0.027(4) 0.022(4) -0.001(3) -0.013(3) 0.001(3) O8 0.018(3) 0.026(4) 0.027(4) 0.000(3) 0.007(3) -0.002(3) O9 0.031(4) 0.018(3) 0.012(3) 0.001(3) 0.003(3) 0.009(3) O10 0.017(9) 0.051(13) 0.050(14) -0.001(11) 0.009(9) -0.001(9) O10' 0.026(9) 0.072(15) 0.036(11) -0.011(14) 0.002(8) -0.008(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 Lu1 O9 2.262(6) . ? Lu1 O8 2.264(5) . ? Lu1 O3 2.328(5) 3_676 ? Lu1 O4 2.381(5) . ? Lu1 O7 2.384(6) 1_454 ? Lu1 O3 2.417(5) 1_554 ? Lu1 O5 2.438(6) . ? Lu1 O6 2.457(6) 1_454 ? Lu1 O2 2.495(5) 1_554 ? Lu1 C10 2.799(8) 1_454 ? Lu1 C8 2.822(8) 1_554 ? C1 O1 1.377(9) . ? C1 C2 1.395(11) . ? C1 C6 1.402(12) . ? C2 C3 1.399(11) . ? C2 C9 1.497(11) . ? C3 C4 1.375(11) . ? C3 H3 0.9300 . ? C4 C5 1.367(11) . ? C4 H4 0.9300 . ? C5 C6 1.386(11) . ? C5 C10 1.507(10) . ? C6 H6 0.9300 . ? C7 O1 1.418(10) . ? C7 C8 1.516(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O2 1.247(10) . ? C8 O3 1.259(9) . ? C8 Lu1 2.822(8) 1_556 ? C9 O5 1.264(9) . ? C9 O4 1.265(9) . ? C10 O7 1.255(11) . ? C10 O6 1.264(11) . ? C10 Lu1 2.799(8) 1_656 ? O2 Lu1 2.495(5) 1_556 ? O3 Lu1 2.328(5) 3_676 ? O3 Lu1 2.417(5) 1_556 ? O6 Lu1 2.457(6) 1_656 ? O7 Lu1 2.384(6) 1_656 ? O8 H8A 0.8495 . ? O8 H8B 0.8502 . ? O9 H9A 0.8549 . ? O9 H9B 0.8553 . ? O10 O10' 0.81(2) . ? 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 O9 Lu1 O8 83.7(2) . . ? O9 Lu1 O3 149.19(19) . 3_676 ? O8 Lu1 O3 80.1(2) . 3_676 ? O9 Lu1 O4 78.8(2) . . ? O8 Lu1 O4 126.8(2) . . ? O3 Lu1 O4 90.1(2) 3_676 . ? O9 Lu1 O7 123.6(2) . 1_454 ? O8 Lu1 O7 77.4(2) . 1_454 ? O3 Lu1 O7 78.0(2) 3_676 1_454 ? O4 Lu1 O7 151.1(2) . 1_454 ? O9 Lu1 O3 134.64(19) . 1_554 ? O8 Lu1 O3 141.5(2) . 1_554 ? O3 Lu1 O3 66.7(2) 3_676 1_554 ? O4 Lu1 O3 74.1(2) . 1_554 ? O7 Lu1 O3 77.0(2) 1_454 1_554 ? O9 Lu1 O5 75.63(19) . . ? O8 Lu1 O5 73.46(19) . . ? O3 Lu1 O5 74.69(19) 3_676 . ? O4 Lu1 O5 53.64(18) . . ? O7 Lu1 O5 142.8(2) 1_454 . ? O3 Lu1 O5 113.53(18) 1_554 . ? O9 Lu1 O6 71.9(2) . 1_454 ? O8 Lu1 O6 82.1(2) . 1_454 ? O3 Lu1 O6 130.75(19) 3_676 1_454 ? O4 Lu1 O6 136.0(2) . 1_454 ? O7 Lu1 O6 53.3(2) 1_454 1_454 ? O3 Lu1 O6 104.52(19) 1_554 1_454 ? O5 Lu1 O6 141.1(2) . 1_454 ? O9 Lu1 O2 86.0(2) . 1_554 ? O8 Lu1 O2 152.3(2) . 1_554 ? O3 Lu1 O2 119.24(19) 3_676 1_554 ? O4 Lu1 O2 75.76(19) . 1_554 ? O7 Lu1 O2 87.1(2) 1_454 1_554 ? O3 Lu1 O2 52.51(19) 1_554 1_554 ? O5 Lu1 O2 128.34(18) . 1_554 ? O6 Lu1 O2 70.23(19) 1_454 1_554 ? O9 Lu1 C10 98.0(3) . 1_454 ? O8 Lu1 C10 78.6(2) . 1_454 ? O3 Lu1 C10 104.3(3) 3_676 1_454 ? O4 Lu1 C10 153.2(2) . 1_454 ? O7 Lu1 C10 26.5(3) 1_454 1_454 ? O3 Lu1 C10 90.7(2) 1_554 1_454 ? O5 Lu1 C10 151.8(2) . 1_454 ? O6 Lu1 C10 26.8(2) 1_454 1_454 ? O2 Lu1 C10 77.5(2) 1_554 1_454 ? O9 Lu1 C8 111.2(2) . 1_554 ? O8 Lu1 C8 157.0(2) . 1_554 ? O3 Lu1 C8 93.0(2) 3_676 1_554 ? O4 Lu1 C8 74.7(2) . 1_554 ? O7 Lu1 C8 79.7(2) 1_454 1_554 ? O3 Lu1 C8 26.4(2) 1_554 1_554 ? O5 Lu1 C8 126.2(2) . 1_554 ? O6 Lu1 C8 86.0(2) 1_454 1_554 ? O2 Lu1 C8 26.2(2) 1_554 1_554 ? C10 Lu1 C8 81.9(2) 1_454 1_554 ? O1 C1 C2 116.7(7) . . ? O1 C1 C6 123.4(7) . . ? C2 C1 C6 119.9(7) . . ? C1 C2 C3 118.2(8) . . ? C1 C2 C9 123.3(7) . . ? C3 C2 C9 118.6(7) . . ? C4 C3 C2 121.8(8) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C5 C4 C3 119.6(8) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.7(7) . . ? C4 C5 C10 120.9(7) . . ? C6 C5 C10 118.5(7) . . ? C5 C6 C1 119.8(7) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O1 C7 C8 113.7(7) . . ? O1 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? O1 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? O2 C8 O3 120.3(7) . . ? O2 C8 C7 122.1(7) . . ? O3 C8 C7 117.5(7) . . ? O2 C8 Lu1 62.1(4) . 1_556 ? O3 C8 Lu1 58.6(4) . 1_556 ? C7 C8 Lu1 170.8(6) . 1_556 ? O5 C9 O4 118.6(7) . . ? O5 C9 C2 121.8(7) . . ? O4 C9 C2 119.5(7) . . ? O7 C10 O6 119.3(7) . . ? O7 C10 C5 121.7(9) . . ? O6 C10 C5 118.9(9) . . ? O7 C10 Lu1 58.0(4) . 1_656 ? O6 C10 Lu1 61.3(4) . 1_656 ? C5 C10 Lu1 178.0(5) . 1_656 ? C1 O1 C7 119.6(7) . . ? C8 O2 Lu1 91.7(5) . 1_556 ? C8 O3 Lu1 151.3(5) . 3_676 ? C8 O3 Lu1 95.0(5) . 1_556 ? Lu1 O3 Lu1 113.3(2) 3_676 1_556 ? C9 O4 Lu1 94.9(5) . . ? C9 O5 Lu1 92.3(5) . . ? C10 O6 Lu1 91.8(5) . 1_656 ? C10 O7 Lu1 95.5(5) . 1_656 ? Lu1 O8 H8A 128.6 . . ? Lu1 O8 H8B 107.9 . . ? H8A O8 H8B 110.8 . . ? Lu1 O9 H9A 117.0 . . ? Lu1 O9 H9B 123.0 . . ? H9A O9 H9B 116.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 178.4(8) . . . . ? C6 C1 C2 C3 0.8(13) . . . . ? O1 C1 C2 C9 -1.3(13) . . . . ? C6 C1 C2 C9 -178.9(8) . . . . ? C1 C2 C3 C4 0.7(14) . . . . ? C9 C2 C3 C4 -179.6(8) . . . . ? C2 C3 C4 C5 -0.5(15) . . . . ? C3 C4 C5 C6 -1.2(14) . . . . ? C3 C4 C5 C10 178.1(8) . . . . ? C4 C5 C6 C1 2.6(13) . . . . ? C10 C5 C6 C1 -176.7(8) . . . . ? O1 C1 C6 C5 -179.9(8) . . . . ? C2 C1 C6 C5 -2.4(13) . . . . ? O1 C7 C8 O2 7.9(12) . . . . ? O1 C7 C8 O3 -168.9(7) . . . . ? O1 C7 C8 Lu1 -106(4) . . . 1_556 ? C1 C2 C9 O5 -38.9(13) . . . . ? C3 C2 C9 O5 141.4(9) . . . . ? C1 C2 C9 O4 139.5(9) . . . . ? C3 C2 C9 O4 -40.2(13) . . . . ? C4 C5 C10 O7 141.7(9) . . . . ? C6 C5 C10 O7 -39.0(12) . . . . ? C4 C5 C10 O6 -40.8(12) . . . . ? C6 C5 C10 O6 138.5(9) . . . . ? C4 C5 C10 Lu1 -137(21) . . . 1_656 ? C6 C5 C10 Lu1 42(22) . . . 1_656 ? C2 C1 O1 C7 -173.6(8) . . . . ? C6 C1 O1 C7 4.0(12) . . . . ? C8 C7 O1 C1 -94.4(9) . . . . ? O3 C8 O2 Lu1 6.3(8) . . . 1_556 ? C7 C8 O2 Lu1 -170.5(7) . . . 1_556 ? O2 C8 O3 Lu1 -177.4(7) . . . 3_676 ? C7 C8 O3 Lu1 -0.6(15) . . . 3_676 ? Lu1 C8 O3 Lu1 -170.9(11) 1_556 . . 3_676 ? O2 C8 O3 Lu1 -6.5(8) . . . 1_556 ? C7 C8 O3 Lu1 170.4(6) . . . 1_556 ? O5 C9 O4 Lu1 7.1(8) . . . . ? C2 C9 O4 Lu1 -171.4(7) . . . . ? O9 Lu1 O4 C9 -84.3(5) . . . . ? O8 Lu1 O4 C9 -10.9(7) . . . . ? O3 Lu1 O4 C9 66.8(5) 3_676 . . . ? O7 Lu1 O4 C9 131.5(6) 1_454 . . . ? O3 Lu1 O4 C9 132.5(6) 1_554 . . . ? O5 Lu1 O4 C9 -4.0(5) . . . . ? O6 Lu1 O4 C9 -132.9(5) 1_454 . . . ? O2 Lu1 O4 C9 -173.0(6) 1_554 . . . ? C10 Lu1 O4 C9 -169.9(6) 1_454 . . . ? C8 Lu1 O4 C9 159.9(6) 1_554 . . . ? O4 C9 O5 Lu1 -6.9(8) . . . . ? C2 C9 O5 Lu1 171.5(8) . . . . ? O9 Lu1 O5 C9 90.6(5) . . . . ? O8 Lu1 O5 C9 178.2(5) . . . . ? O3 Lu1 O5 C9 -97.7(5) 3_676 . . . ? O4 Lu1 O5 C9 4.0(5) . . . . ? O7 Lu1 O5 C9 -141.9(5) 1_454 . . . ? O3 Lu1 O5 C9 -42.2(5) 1_554 . . . ? O6 Lu1 O5 C9 124.7(5) 1_454 . . . ? O2 Lu1 O5 C9 17.7(6) 1_554 . . . ? C10 Lu1 O5 C9 170.5(6) 1_454 . . . ? C8 Lu1 O5 C9 -15.3(6) 1_554 . . . ? O7 C10 O6 Lu1 -0.2(8) . . . 1_656 ? C5 C10 O6 Lu1 -177.7(6) . . . 1_656 ? O6 C10 O7 Lu1 0.2(8) . . . 1_656 ? C5 C10 O7 Lu1 177.7(6) . . . 1_656 ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.004 _refine_diff_density_min -1.009 _refine_diff_density_rms 0.181 data_5 _database_code_depnum_ccdc_archive 'CCDC 906614' #TrackingRef '906614.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 Nd O10' _chemical_formula_weight 435.43 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' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 19.808(4) _cell_length_b 9.989(2) _cell_length_c 6.9059(14) _cell_angle_alpha 90.00 _cell_angle_beta 106.03(3) _cell_angle_gamma 90.00 _cell_volume 1313.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1085 _cell_measurement_theta_min 2.5105 _cell_measurement_theta_max 28.7933 _exptl_crystal_description purple _exptl_crystal_colour colourless _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 4.004 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7669 _exptl_absorpt_correction_T_max 0.8562 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number 3908 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3953 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0328 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.59 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2026 _reflns_number_gt 1962 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _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^)+(0.0267P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.026(17) _refine_ls_number_reflns 2026 _refine_ls_number_parameters 190 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0215 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0484 _refine_ls_wR_factor_gt 0.0480 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.033 _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 Nd1 Nd 0.85190(4) 0.760395(18) 0.55764(8) 0.00677(8) Uani 1 1 d . . . C1 C 0.6788(3) 0.6582(5) 0.5742(8) 0.0093(11) Uani 1 1 d . . . C2 C 0.6988(2) 0.5242(5) 0.5960(8) 0.0091(11) Uani 1 1 d . . . C3 C 0.6469(2) 0.4277(5) 0.5220(7) 0.0073(10) Uani 1 1 d U . . H3 H 0.6586 0.3375 0.5403 0.009 Uiso 1 1 calc R . . C4 C 0.5785(2) 0.4628(5) 0.4221(8) 0.0102(11) Uani 1 1 d . . . H4 H 0.5453 0.3975 0.3668 0.012 Uiso 1 1 calc R . . C5 C 0.5602(2) 0.5977(5) 0.4058(8) 0.0078(10) Uani 1 1 d . . . C6 C 0.6101(2) 0.6963(5) 0.4814(8) 0.0084(11) Uani 1 1 d . . . H6 H 0.5976 0.7863 0.4700 0.010 Uiso 1 1 calc R . . C7 C 0.7100(2) 0.8767(4) 0.7215(8) 0.0097(11) Uani 1 1 d . . . H7A H 0.6813 0.8603 0.8124 0.012 Uiso 1 1 calc R . . H7B H 0.6832 0.9306 0.6097 0.012 Uiso 1 1 calc R . . C8 C 0.7774(3) 0.9481(5) 0.8310(8) 0.0121(11) Uani 1 1 d . . . C9 C 0.7726(3) 0.4768(5) 0.7020(7) 0.0084(11) Uani 1 1 d . . . C10 C 0.4868(3) 0.6423(5) 0.2978(8) 0.0095(11) Uani 1 1 d . . . O1 O 0.7305(2) 0.7524(3) 0.6497(6) 0.0127(9) Uani 1 1 d . . . O2 O 0.83468(18) 0.8893(4) 0.8435(6) 0.0142(9) Uani 1 1 d . . . O3 O 0.77042(19) 1.0594(4) 0.8998(6) 0.0119(9) Uani 1 1 d U . . O4 O 0.82439(18) 0.5558(3) 0.7154(5) 0.0131(8) Uani 1 1 d . . . O5 O 0.77921(18) 0.3615(3) 0.7743(5) 0.0112(8) Uani 1 1 d . . . O6 O 0.44885(18) 0.5676(4) 0.1635(6) 0.0107(9) Uani 1 1 d . . . O7 O 0.4650(2) 0.7533(3) 0.3402(6) 0.0130(9) Uani 1 1 d . . . O8 O 0.89379(19) 0.8277(4) 0.2608(6) 0.0146(9) Uani 1 1 d . . . H8A H 0.8707 0.8080 0.1418 0.018 Uiso 1 1 d R . . H8B H 0.9123 0.9045 0.2672 0.018 Uiso 1 1 d R . . O9 O 0.92993(18) 0.5811(3) 0.4837(6) 0.0130(8) Uani 1 1 d . . . H9A H 0.8966 0.5337 0.4033 0.016 Uiso 1 1 d R . . H9B H 0.9623 0.5284 0.5551 0.016 Uiso 1 1 d R . . O10 O 1.0151(2) 0.3913(4) 0.7139(6) 0.0224(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Nd1 0.00572(12) 0.00542(12) 0.00773(13) -0.0001(2) -0.00052(9) -0.0005(2) C1 0.011(2) 0.006(2) 0.009(3) -0.0004(19) 0.000(2) -0.0019(19) C2 0.006(2) 0.014(3) 0.008(3) 0.004(2) 0.003(2) 0.003(2) C3 0.0082(13) 0.0069(13) 0.0071(13) 0.0002(9) 0.0027(9) -0.0004(9) C4 0.016(3) 0.005(2) 0.008(3) -0.0015(19) 0.000(2) -0.0029(19) C5 0.008(2) 0.009(2) 0.008(3) 0.0004(19) 0.006(2) 0.0014(19) C6 0.004(2) 0.010(3) 0.009(3) -0.001(2) -0.001(2) 0.002(2) C7 0.011(3) 0.006(3) 0.012(3) -0.004(2) 0.002(2) -0.0010(19) C8 0.016(3) 0.009(3) 0.011(3) 0.002(2) 0.003(2) 0.003(2) C9 0.010(3) 0.006(3) 0.006(3) -0.001(2) -0.003(2) 0.001(2) C10 0.010(2) 0.005(3) 0.015(3) -0.001(2) 0.006(2) -0.004(2) O1 0.009(2) 0.010(2) 0.018(2) -0.0036(13) 0.0030(18) -0.0027(13) O2 0.0124(19) 0.013(2) 0.016(2) -0.0009(16) 0.0015(17) 0.0009(15) O3 0.0120(12) 0.0113(12) 0.0123(12) -0.0019(9) 0.0033(9) -0.0022(9) O4 0.0100(19) 0.0105(18) 0.017(2) 0.0058(15) 0.0003(16) -0.0006(15) O5 0.0105(17) 0.0049(18) 0.015(2) 0.0019(14) -0.0018(16) 0.0002(13) O6 0.0091(18) 0.011(2) 0.011(2) 0.0014(16) 0.0013(16) -0.0014(15) O7 0.0086(19) 0.013(2) 0.016(2) -0.0010(13) 0.0004(17) 0.0016(13) O8 0.017(2) 0.010(2) 0.013(2) 0.0003(16) -0.0035(16) -0.0060(16) O9 0.0087(18) 0.012(2) 0.015(2) -0.0019(15) -0.0025(16) 0.0031(14) O10 0.026(2) 0.020(2) 0.021(2) -0.0017(16) 0.0051(19) 0.0077(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Nd1 O5 2.414(3) 2_564 ? Nd1 O4 2.447(3) . ? Nd1 O2 2.459(4) . ? Nd1 O3 2.462(4) 2_574 ? Nd1 O8 2.507(4) . ? Nd1 O9 2.508(4) . ? Nd1 O6 2.530(4) 4_565 ? Nd1 O7 2.535(4) 4_565 ? Nd1 O1 2.652(4) . ? Nd1 C10 2.896(5) 4_565 ? C1 O1 1.382(6) . ? C1 C6 1.389(7) . ? C1 C2 1.392(7) . ? C2 C3 1.399(6) . ? C2 C9 1.519(6) . ? C3 C4 1.385(6) . ? C3 H3 0.9300 . ? C4 C5 1.392(6) . ? C4 H4 0.9300 . ? C5 C6 1.390(6) . ? C5 C10 1.508(6) . ? C6 H6 0.9300 . ? C7 O1 1.437(5) . ? C7 C8 1.518(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O3 1.232(6) . ? C8 O2 1.259(6) . ? C9 O5 1.248(6) . ? C9 O4 1.277(6) . ? C10 O7 1.254(6) . ? C10 O6 1.264(6) . ? C10 Nd1 2.896(5) 4_464 ? O3 Nd1 2.462(4) 2_575 ? O5 Nd1 2.414(3) 2_565 ? O6 Nd1 2.530(4) 4_464 ? O7 Nd1 2.535(4) 4_464 ? O8 H8A 0.8459 . ? O8 H8B 0.8459 . ? O9 H9A 0.8751 . ? O9 H9B 0.8698 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Nd1 O4 77.49(12) 2_564 . ? O5 Nd1 O2 136.97(12) 2_564 . ? O4 Nd1 O2 88.99(12) . . ? O5 Nd1 O3 80.71(13) 2_564 2_574 ? O4 Nd1 O3 127.47(12) . 2_574 ? O2 Nd1 O3 75.71(13) . 2_574 ? O5 Nd1 O8 74.36(12) 2_564 . ? O4 Nd1 O8 138.84(13) . . ? O2 Nd1 O8 131.84(14) . . ? O3 Nd1 O8 76.49(13) 2_574 . ? O5 Nd1 O9 74.81(12) 2_564 . ? O4 Nd1 O9 73.75(12) . . ? O2 Nd1 O9 140.12(13) . . ? O3 Nd1 O9 142.86(14) 2_574 . ? O8 Nd1 O9 70.31(13) . . ? O5 Nd1 O6 144.30(13) 2_564 4_565 ? O4 Nd1 O6 133.09(13) . 4_565 ? O2 Nd1 O6 71.02(13) . 4_565 ? O3 Nd1 O6 89.07(10) 2_574 4_565 ? O8 Nd1 O6 70.00(12) . 4_565 ? O9 Nd1 O6 94.74(12) . 4_565 ? O5 Nd1 O7 143.02(11) 2_564 4_565 ? O4 Nd1 O7 82.54(11) . 4_565 ? O2 Nd1 O7 72.50(12) . 4_565 ? O3 Nd1 O7 135.40(12) 2_574 4_565 ? O8 Nd1 O7 102.85(13) . 4_565 ? O9 Nd1 O7 69.83(12) . 4_565 ? O6 Nd1 O7 51.36(11) 4_565 4_565 ? O5 Nd1 O1 78.57(13) 2_564 . ? O4 Nd1 O1 62.61(11) . . ? O2 Nd1 O1 59.16(12) . . ? O3 Nd1 O1 66.51(12) 2_574 . ? O8 Nd1 O1 136.96(12) . . ? O9 Nd1 O1 132.65(10) . . ? O6 Nd1 O1 128.11(12) 4_565 . ? O7 Nd1 O1 118.71(13) 4_565 . ? O5 Nd1 C10 151.99(14) 2_564 4_565 ? O4 Nd1 C10 107.99(13) . 4_565 ? O2 Nd1 C10 71.04(13) . 4_565 ? O3 Nd1 C10 113.36(13) 2_574 4_565 ? O8 Nd1 C10 85.24(14) . 4_565 ? O9 Nd1 C10 80.40(13) . 4_565 ? O6 Nd1 C10 25.83(12) 4_565 4_565 ? O7 Nd1 C10 25.60(12) 4_565 4_565 ? O1 Nd1 C10 128.82(14) . 4_565 ? O1 C1 C6 121.2(4) . . ? O1 C1 C2 117.1(4) . . ? C6 C1 C2 121.7(4) . . ? C1 C2 C3 117.7(4) . . ? C1 C2 C9 124.0(4) . . ? C3 C2 C9 118.3(4) . . ? C4 C3 C2 121.7(4) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C5 118.8(4) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C6 C5 C4 120.9(4) . . ? C6 C5 C10 117.7(4) . . ? C4 C5 C10 121.3(4) . . ? C1 C6 C5 118.9(4) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? O1 C7 C8 106.5(4) . . ? O1 C7 H7A 110.4 . . ? C8 C7 H7A 110.4 . . ? O1 C7 H7B 110.4 . . ? C8 C7 H7B 110.4 . . ? H7A C7 H7B 108.6 . . ? O3 C8 O2 126.1(5) . . ? O3 C8 C7 116.0(4) . . ? O2 C8 C7 117.9(4) . . ? O5 C9 O4 123.2(4) . . ? O5 C9 C2 117.5(4) . . ? O4 C9 C2 119.3(4) . . ? O7 C10 O6 121.4(4) . . ? O7 C10 C5 119.6(4) . . ? O6 C10 C5 119.1(4) . . ? O7 C10 Nd1 60.9(3) . 4_464 ? O6 C10 Nd1 60.7(2) . 4_464 ? C5 C10 Nd1 173.9(4) . 4_464 ? C1 O1 C7 117.9(4) . . ? C1 O1 Nd1 123.8(3) . . ? C7 O1 Nd1 114.7(3) . . ? C8 O2 Nd1 120.7(3) . . ? C8 O3 Nd1 134.5(3) . 2_575 ? C9 O4 Nd1 139.2(3) . . ? C9 O5 Nd1 139.7(3) . 2_565 ? C10 O6 Nd1 93.5(3) . 4_464 ? C10 O7 Nd1 93.5(3) . 4_464 ? Nd1 O8 H8A 121.3 . . ? Nd1 O8 H8B 115.9 . . ? H8A O8 H8B 111.9 . . ? Nd1 O9 H9A 96.7 . . ? Nd1 O9 H9B 135.7 . . ? H9A O9 H9B 109.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 179.4(5) . . . . ? C6 C1 C2 C3 -0.4(8) . . . . ? O1 C1 C2 C9 1.8(8) . . . . ? C6 C1 C2 C9 -178.0(5) . . . . ? C1 C2 C3 C4 2.8(8) . . . . ? C9 C2 C3 C4 -179.4(5) . . . . ? C2 C3 C4 C5 -3.8(8) . . . . ? C3 C4 C5 C6 2.4(8) . . . . ? C3 C4 C5 C10 179.6(5) . . . . ? O1 C1 C6 C5 179.2(5) . . . . ? C2 C1 C6 C5 -1.0(8) . . . . ? C4 C5 C6 C1 0.0(8) . . . . ? C10 C5 C6 C1 -177.3(5) . . . . ? O1 C7 C8 O3 178.3(5) . . . . ? O1 C7 C8 O2 -1.8(6) . . . . ? C1 C2 C9 O5 155.3(5) . . . . ? C3 C2 C9 O5 -22.3(7) . . . . ? C1 C2 C9 O4 -23.9(8) . . . . ? C3 C2 C9 O4 158.5(5) . . . . ? C6 C5 C10 O7 -26.6(7) . . . . ? C4 C5 C10 O7 156.2(5) . . . . ? C6 C5 C10 O6 152.3(5) . . . . ? C4 C5 C10 O6 -25.0(7) . . . . ? C6 C5 C10 Nd1 66(3) . . . 4_464 ? C4 C5 C10 Nd1 -111(3) . . . 4_464 ? C6 C1 O1 C7 30.1(7) . . . . ? C2 C1 O1 C7 -149.7(5) . . . . ? C6 C1 O1 Nd1 -127.4(4) . . . . ? C2 C1 O1 Nd1 52.8(6) . . . . ? C8 C7 O1 C1 169.3(4) . . . . ? C8 C7 O1 Nd1 -31.3(5) . . . . ? O5 Nd1 O1 C1 22.5(3) 2_564 . . . ? O4 Nd1 O1 C1 -59.2(3) . . . . ? O2 Nd1 O1 C1 -165.9(4) . . . . ? O3 Nd1 O1 C1 107.2(4) 2_574 . . . ? O8 Nd1 O1 C1 74.2(4) . . . . ? O9 Nd1 O1 C1 -34.2(4) . . . . ? O6 Nd1 O1 C1 175.9(3) 4_565 . . . ? O7 Nd1 O1 C1 -122.5(3) 4_565 . . . ? C10 Nd1 O1 C1 -150.9(3) 4_565 . . . ? O5 Nd1 O1 C7 -135.6(3) 2_564 . . . ? O4 Nd1 O1 C7 142.7(4) . . . . ? O2 Nd1 O1 C7 36.0(3) . . . . ? O3 Nd1 O1 C7 -50.9(3) 2_574 . . . ? O8 Nd1 O1 C7 -83.9(4) . . . . ? O9 Nd1 O1 C7 167.7(3) . . . . ? O6 Nd1 O1 C7 17.8(4) 4_565 . . . ? O7 Nd1 O1 C7 79.5(3) 4_565 . . . ? C10 Nd1 O1 C7 51.0(4) 4_565 . . . ? O3 C8 O2 Nd1 -140.6(5) . . . . ? C7 C8 O2 Nd1 39.5(6) . . . . ? O5 Nd1 O2 C8 -27.8(5) 2_564 . . . ? O4 Nd1 O2 C8 -98.1(4) . . . . ? O3 Nd1 O2 C8 31.1(4) 2_574 . . . ? O8 Nd1 O2 C8 87.6(4) . . . . ? O9 Nd1 O2 C8 -160.9(3) . . . . ? O6 Nd1 O2 C8 125.1(4) 4_565 . . . ? O7 Nd1 O2 C8 179.4(4) 4_565 . . . ? O1 Nd1 O2 C8 -39.8(4) . . . . ? C10 Nd1 O2 C8 152.4(4) 4_565 . . . ? O2 C8 O3 Nd1 7.8(9) . . . 2_575 ? C7 C8 O3 Nd1 -172.2(3) . . . 2_575 ? O5 C9 O4 Nd1 162.9(4) . . . . ? C2 C9 O4 Nd1 -17.9(8) . . . . ? O5 Nd1 O4 C9 -39.3(5) 2_564 . . . ? O2 Nd1 O4 C9 99.5(5) . . . . ? O3 Nd1 O4 C9 28.5(6) 2_574 . . . ? O8 Nd1 O4 C9 -87.0(5) . . . . ? O9 Nd1 O4 C9 -116.9(5) . . . . ? O6 Nd1 O4 C9 162.0(5) 4_565 . . . ? O7 Nd1 O4 C9 172.0(5) 4_565 . . . ? O1 Nd1 O4 C9 44.2(5) . . . . ? C10 Nd1 O4 C9 169.2(5) 4_565 . . . ? O4 C9 O5 Nd1 33.2(9) . . . 2_565 ? C2 C9 O5 Nd1 -145.9(4) . . . 2_565 ? O7 C10 O6 Nd1 5.8(5) . . . 4_464 ? C5 C10 O6 Nd1 -173.0(4) . . . 4_464 ? O6 C10 O7 Nd1 -5.8(5) . . . 4_464 ? C5 C10 O7 Nd1 173.0(4) . . . 4_464 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.579 _refine_diff_density_min -0.459 _refine_diff_density_rms 0.093 data_1 _database_code_depnum_ccdc_archive 'CCDC 906615' #TrackingRef '906615.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 O10 Pr' _chemical_formula_weight 432.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 19.115(4) _cell_length_b 9.6740(19) _cell_length_c 6.6627(13) _cell_angle_alpha 90.00 _cell_angle_beta 106.72(3) _cell_angle_gamma 90.00 _cell_volume 1180.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1085 _cell_measurement_theta_min 2.5105 _cell_measurement_theta_max 28.7933 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 4.185 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7582 _exptl_absorpt_correction_T_max 0.8504 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number 3908 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3333 _diffrn_reflns_av_R_equivalents 0.0776 _diffrn_reflns_av_sigmaI/netI 0.0981 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1695 _reflns_number_gt 1677 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _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^)+(0.0445P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(3) _refine_ls_number_reflns 1695 _refine_ls_number_parameters 190 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1097 _refine_ls_wR_factor_gt 0.1093 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.054 _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 0.44837(13) 0.73953(4) 0.0244(3) 0.0131(2) Uani 1 1 d . . . C1 C 0.6205(4) 0.8406(10) 0.0049(12) 0.0153(17) Uani 1 1 d . . . C2 C 0.6013(4) 0.9740(9) -0.0153(12) 0.0142(17) Uani 1 1 d . . . C3 C 0.6536(4) 1.0709(9) 0.0577(12) 0.0134(16) Uani 1 1 d . . . H3 H 0.6415 1.1640 0.0368 0.016 Uiso 1 1 calc R . . C4 C 0.7213(4) 1.0355(9) 0.1580(13) 0.0169(18) Uani 1 1 d . . . H4 H 0.7560 1.1027 0.2158 0.020 Uiso 1 1 calc R . . C5 C 0.7391(4) 0.9016(9) 0.1752(11) 0.0141(17) Uani 1 1 d . . . C6 C 0.6898(5) 0.8031(11) 0.0995(15) 0.0209(19) Uani 1 1 d . . . H6 H 0.7031 0.7104 0.1118 0.025 Uiso 1 1 calc R . . C7 C 0.5899(4) 0.6234(9) -0.1394(14) 0.0189(19) Uani 1 1 d . . . H7A H 0.6193 0.5690 -0.0234 0.023 Uiso 1 1 calc R . . H7B H 0.6183 0.6414 -0.2359 0.023 Uiso 1 1 calc R . . C8 C 0.5222(5) 0.5484(10) -0.2470(14) 0.021(2) Uani 1 1 d . . . C9 C 0.5276(4) 1.0222(10) -0.1231(12) 0.0148(18) Uani 1 1 d . . . C10 C 0.8131(5) 0.8568(10) 0.2807(13) 0.021(2) Uani 1 1 d . . . O1 O 0.5690(6) 0.7478(5) -0.0661(18) 0.020(2) Uani 1 1 d . . . O2 O 0.5297(4) 0.4390(8) -0.3179(11) 0.0262(16) Uani 1 1 d . . . O3 O 0.4658(3) 0.6093(8) -0.2603(10) 0.0268(17) Uani 1 1 d . . . O4 O 0.4767(3) 0.9419(7) -0.1346(10) 0.0212(14) Uani 1 1 d . . . O5 O 0.5208(3) 1.1355(6) -0.1943(9) 0.0174(13) Uani 1 1 d . . . O6 O 0.8509(3) 0.9331(7) 0.4170(9) 0.0182(15) Uani 1 1 d . . . O7 O 0.8342(6) 0.7475(5) 0.2427(19) 0.022(2) Uani 1 1 d U . . O8 O 0.4057(4) 0.6719(8) 0.3206(9) 0.0265(16) Uani 1 1 d . . . H8A H 0.4252 0.7043 0.4418 0.032 Uiso 1 1 d R . . H8B H 0.3810 0.5984 0.3167 0.032 Uiso 1 1 d R . . O9 O 0.3706(3) 0.9203(7) 0.0960(11) 0.0253(15) Uani 1 1 d . . . H9A H 0.3833 0.9660 0.2120 0.030 Uiso 1 1 d R . . H9B H 0.3488 0.9787 0.0044 0.030 Uiso 1 1 d R . . O10 O 0.7832(4) 0.6098(10) 0.8627(12) 0.047(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 Pr1 0.0086(3) 0.0122(3) 0.0159(3) 0.0003(5) -0.0007(2) -0.0008(5) C1 0.013(4) 0.016(5) 0.015(3) 0.001(4) 0.001(3) -0.004(3) C2 0.012(4) 0.017(5) 0.014(4) 0.007(4) 0.004(3) 0.007(3) C3 0.015(4) 0.011(5) 0.015(3) 0.000(3) 0.004(3) 0.000(3) C4 0.012(4) 0.016(5) 0.022(4) -0.004(4) 0.004(3) -0.007(3) C5 0.006(3) 0.020(5) 0.013(4) 0.001(3) -0.002(3) -0.001(3) C6 0.015(4) 0.018(6) 0.027(5) 0.003(5) 0.002(4) 0.010(4) C7 0.014(4) 0.011(5) 0.029(5) -0.008(4) 0.002(3) 0.002(3) C8 0.024(5) 0.017(5) 0.020(4) -0.008(4) 0.004(4) -0.005(4) C9 0.012(4) 0.016(5) 0.013(4) -0.001(4) -0.002(3) 0.001(4) C10 0.020(4) 0.017(5) 0.026(5) 0.009(4) 0.008(4) 0.010(4) O1 0.006(5) 0.025(6) 0.028(6) -0.002(2) 0.007(5) -0.003(2) O2 0.026(3) 0.018(4) 0.035(4) -0.011(4) 0.009(3) -0.010(3) O3 0.015(3) 0.037(5) 0.026(3) -0.014(3) 0.002(3) 0.001(3) O4 0.011(3) 0.019(4) 0.029(4) 0.009(3) -0.002(2) 0.003(3) O5 0.015(3) 0.010(4) 0.023(3) 0.009(3) 0.000(2) 0.003(2) O6 0.011(3) 0.013(4) 0.024(3) -0.006(3) -0.005(2) 0.000(3) O7 0.017(4) 0.020(4) 0.024(4) 0.005(2) -0.003(3) 0.002(2) O8 0.033(4) 0.023(5) 0.023(3) 0.007(3) 0.007(3) -0.004(3) O9 0.020(3) 0.027(4) 0.027(3) -0.003(3) 0.004(2) 0.002(3) O10 0.039(4) 0.052(6) 0.047(4) -0.002(4) 0.011(3) 0.009(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 O5 2.324(6) 2_575 ? Pr1 O2 2.359(7) 2_565 ? Pr1 O4 2.362(7) . ? Pr1 O3 2.379(7) . ? Pr1 O9 2.430(7) . ? Pr1 O8 2.432(7) . ? Pr1 O7 2.438(11) 4_464 ? Pr1 O6 2.451(7) 4_464 ? Pr1 O1 2.548(11) . ? Pr1 C10 2.788(9) 4_464 ? C1 O1 1.314(13) . ? C1 C2 1.337(12) . ? C1 C6 1.343(12) . ? C2 C3 1.355(12) . ? C2 C9 1.461(10) . ? C3 C4 1.319(11) . ? C3 H3 0.9300 . ? C4 C5 1.337(12) . ? C4 H4 0.9300 . ? C5 C6 1.333(13) . ? C5 C10 1.453(10) . ? C6 H6 0.9300 . ? C7 O1 1.399(11) . ? C7 C8 1.476(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O2 1.184(11) . ? C8 O3 1.210(10) . ? C9 O5 1.187(11) . ? C9 O4 1.231(11) . ? C10 O7 1.185(12) . ? C10 O6 1.230(11) . ? C10 Pr1 2.788(9) 4_565 ? O2 Pr1 2.359(7) 2_564 ? O5 Pr1 2.324(6) 2_574 ? O6 Pr1 2.451(7) 4_565 ? O7 Pr1 2.438(11) 4_565 ? O8 H8A 0.8457 . ? O8 H8B 0.8503 . ? O9 H9A 0.8626 . ? O9 H9B 0.8482 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Pr1 O2 81.8(3) 2_575 2_565 ? O5 Pr1 O4 76.7(2) 2_575 . ? O2 Pr1 O4 126.9(3) 2_565 . ? O5 Pr1 O3 137.0(3) 2_575 . ? O2 Pr1 O3 75.0(3) 2_565 . ? O4 Pr1 O3 88.8(3) . . ? O5 Pr1 O9 74.0(2) 2_575 . ? O2 Pr1 O9 143.3(3) 2_565 . ? O4 Pr1 O9 73.9(2) . . ? O3 Pr1 O9 140.5(3) . . ? O5 Pr1 O8 75.3(2) 2_575 . ? O2 Pr1 O8 76.9(3) 2_565 . ? O4 Pr1 O8 139.5(3) . . ? O3 Pr1 O8 131.4(3) . . ? O9 Pr1 O8 70.6(3) . . ? O5 Pr1 O7 142.0(2) 2_575 4_464 ? O2 Pr1 O7 135.2(2) 2_565 4_464 ? O4 Pr1 O7 83.2(3) . 4_464 ? O3 Pr1 O7 73.3(3) . 4_464 ? O9 Pr1 O7 69.6(3) . 4_464 ? O8 Pr1 O7 101.8(3) . 4_464 ? O5 Pr1 O6 144.8(3) 2_575 4_464 ? O2 Pr1 O6 88.85(19) 2_565 4_464 ? O4 Pr1 O6 133.4(3) . 4_464 ? O3 Pr1 O6 71.1(2) . 4_464 ? O9 Pr1 O6 95.2(3) . 4_464 ? O8 Pr1 O6 69.5(2) . 4_464 ? O7 Pr1 O6 51.2(2) 4_464 4_464 ? O5 Pr1 O1 78.7(3) 2_575 . ? O2 Pr1 O1 66.6(3) 2_565 . ? O4 Pr1 O1 61.8(2) . . ? O3 Pr1 O1 58.9(3) . . ? O9 Pr1 O1 132.1(2) . . ? O8 Pr1 O1 137.6(3) . . ? O7 Pr1 O1 119.1(4) 4_464 . ? O6 Pr1 O1 128.1(2) 4_464 . ? O5 Pr1 C10 151.8(3) 2_575 4_464 ? O2 Pr1 C10 113.4(3) 2_565 4_464 ? O4 Pr1 C10 108.0(3) . 4_464 ? O3 Pr1 C10 71.2(2) . 4_464 ? O9 Pr1 C10 80.7(3) . 4_464 ? O8 Pr1 C10 84.9(3) . 4_464 ? O7 Pr1 C10 25.1(3) 4_464 4_464 ? O6 Pr1 C10 26.1(2) 4_464 4_464 ? O1 Pr1 C10 128.6(3) . 4_464 ? O1 C1 C2 117.9(8) . . ? O1 C1 C6 121.3(9) . . ? C2 C1 C6 120.8(9) . . ? C1 C2 C3 118.7(8) . . ? C1 C2 C9 123.7(8) . . ? C3 C2 C9 117.5(8) . . ? C4 C3 C2 121.1(8) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C3 C4 C5 119.0(7) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C6 C5 C4 121.7(8) . . ? C6 C5 C10 117.0(9) . . ? C4 C5 C10 121.3(8) . . ? C5 C6 C1 118.7(9) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? O1 C7 C8 107.1(8) . . ? O1 C7 H7A 110.3 . . ? C8 C7 H7A 110.3 . . ? O1 C7 H7B 110.3 . . ? C8 C7 H7B 110.3 . . ? H7A C7 H7B 108.5 . . ? O2 C8 O3 127.9(9) . . ? O2 C8 C7 116.3(8) . . ? O3 C8 C7 115.8(8) . . ? O5 C9 O4 124.4(8) . . ? O5 C9 C2 118.1(8) . . ? O4 C9 C2 117.6(8) . . ? O7 C10 O6 122.0(10) . . ? O7 C10 C5 120.4(10) . . ? O6 C10 C5 117.4(8) . . ? O7 C10 Pr1 60.7(7) . 4_565 ? O6 C10 Pr1 61.4(5) . 4_565 ? C5 C10 Pr1 172.8(6) . 4_565 ? C1 O1 C7 117.0(10) . . ? C1 O1 Pr1 124.8(7) . . ? C7 O1 Pr1 115.0(6) . . ? C8 O2 Pr1 133.8(6) . 2_564 ? C8 O3 Pr1 121.7(6) . . ? C9 O4 Pr1 140.7(5) . . ? C9 O5 Pr1 140.7(5) . 2_574 ? C10 O6 Pr1 92.4(6) . 4_565 ? C10 O7 Pr1 94.2(7) . 4_565 ? Pr1 O8 H8A 121.1 . . ? Pr1 O8 H8B 120.9 . . ? H8A O8 H8B 115.3 . . ? Pr1 O9 H9A 121.0 . . ? Pr1 O9 H9B 122.7 . . ? H9A O9 H9B 104.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 179.8(9) . . . . ? C6 C1 C2 C3 1.4(12) . . . . ? O1 C1 C2 C9 -3.9(13) . . . . ? C6 C1 C2 C9 177.6(8) . . . . ? C1 C2 C3 C4 -4.0(12) . . . . ? C9 C2 C3 C4 179.5(7) . . . . ? C2 C3 C4 C5 4.3(11) . . . . ? C3 C4 C5 C6 -2.1(12) . . . . ? C3 C4 C5 C10 178.9(8) . . . . ? C4 C5 C6 C1 -0.4(14) . . . . ? C10 C5 C6 C1 178.6(7) . . . . ? O1 C1 C6 C5 -177.6(9) . . . . ? C2 C1 C6 C5 0.8(14) . . . . ? O1 C7 C8 O2 -179.3(9) . . . . ? O1 C7 C8 O3 4.0(12) . . . . ? C1 C2 C9 O5 -155.1(8) . . . . ? C3 C2 C9 O5 21.3(12) . . . . ? C1 C2 C9 O4 24.6(12) . . . . ? C3 C2 C9 O4 -159.1(8) . . . . ? C6 C5 C10 O7 23.9(14) . . . . ? C4 C5 C10 O7 -157.0(10) . . . . ? C6 C5 C10 O6 -152.2(8) . . . . ? C4 C5 C10 O6 26.8(11) . . . . ? C6 C5 C10 Pr1 -73(6) . . . 4_565 ? C4 C5 C10 Pr1 106(5) . . . 4_565 ? C2 C1 O1 C7 149.7(9) . . . . ? C6 C1 O1 C7 -31.9(15) . . . . ? C2 C1 O1 Pr1 -51.4(12) . . . . ? C6 C1 O1 Pr1 127.0(8) . . . . ? C8 C7 O1 C1 -169.3(9) . . . . ? C8 C7 O1 Pr1 29.7(10) . . . . ? O5 Pr1 O1 C1 -22.4(8) 2_575 . . . ? O2 Pr1 O1 C1 -108.3(9) 2_565 . . . ? O4 Pr1 O1 C1 58.4(8) . . . . ? O3 Pr1 O1 C1 165.6(10) . . . . ? O9 Pr1 O1 C1 33.5(10) . . . . ? O8 Pr1 O1 C1 -75.4(9) . . . . ? O7 Pr1 O1 C1 121.5(8) 4_464 . . . ? O6 Pr1 O1 C1 -176.8(8) 4_464 . . . ? C10 Pr1 O1 C1 149.7(8) 4_464 . . . ? O5 Pr1 O1 C7 136.9(8) 2_575 . . . ? O2 Pr1 O1 C7 51.0(7) 2_565 . . . ? O4 Pr1 O1 C7 -142.3(9) . . . . ? O3 Pr1 O1 C7 -35.1(7) . . . . ? O9 Pr1 O1 C7 -167.2(7) . . . . ? O8 Pr1 O1 C7 83.9(9) . . . . ? O7 Pr1 O1 C7 -79.2(8) 4_464 . . . ? O6 Pr1 O1 C7 -17.5(9) 4_464 . . . ? C10 Pr1 O1 C7 -51.0(9) 4_464 . . . ? O3 C8 O2 Pr1 -10.6(17) . . . 2_564 ? C7 C8 O2 Pr1 173.2(6) . . . 2_564 ? O2 C8 O3 Pr1 142.0(9) . . . . ? C7 C8 O3 Pr1 -41.7(11) . . . . ? O5 Pr1 O3 C8 30.1(9) 2_575 . . . ? O2 Pr1 O3 C8 -29.8(7) 2_565 . . . ? O4 Pr1 O3 C8 99.0(7) . . . . ? O9 Pr1 O3 C8 161.6(7) . . . . ? O8 Pr1 O3 C8 -86.6(8) . . . . ? O7 Pr1 O3 C8 -177.7(8) 4_464 . . . ? O6 Pr1 O3 C8 -123.8(8) 4_464 . . . ? O1 Pr1 O3 C8 41.6(7) . . . . ? C10 Pr1 O3 C8 -151.5(8) 4_464 . . . ? O5 C9 O4 Pr1 -161.5(6) . . . . ? C2 C9 O4 Pr1 18.9(14) . . . . ? O5 Pr1 O4 C9 39.0(10) 2_575 . . . ? O2 Pr1 O4 C9 -29.9(11) 2_565 . . . ? O3 Pr1 O4 C9 -100.1(10) . . . . ? O9 Pr1 O4 C9 115.9(10) . . . . ? O8 Pr1 O4 C9 86.4(11) . . . . ? O7 Pr1 O4 C9 -173.4(10) 4_464 . . . ? O6 Pr1 O4 C9 -162.3(9) 4_464 . . . ? O1 Pr1 O4 C9 -45.1(10) . . . . ? C10 Pr1 O4 C9 -169.8(10) 4_464 . . . ? O4 C9 O5 Pr1 -33.3(16) . . . 2_574 ? C2 C9 O5 Pr1 146.3(6) . . . 2_574 ? O7 C10 O6 Pr1 -4.2(11) . . . 4_565 ? C5 C10 O6 Pr1 171.9(6) . . . 4_565 ? O6 C10 O7 Pr1 4.2(11) . . . 4_565 ? C5 C10 O7 Pr1 -171.8(7) . . . 4_565 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.029 _refine_diff_density_min -2.316 _refine_diff_density_rms 0.227 data_5a _database_code_depnum_ccdc_archive 'CCDC 906616' #TrackingRef '906616.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 O10 Tb' _chemical_formula_weight 450.11 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9200(18) _cell_length_b 15.660(3) _cell_length_c 8.9500(18) _cell_angle_alpha 90.00 _cell_angle_beta 100.58(3) _cell_angle_gamma 90.00 _cell_volume 1228.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11782 _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 27.14 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 5.809 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5424 _exptl_absorpt_correction_T_max 0.6536 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number 3908 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9898 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2159 _reflns_number_gt 1792 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _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^)+(0.0244P)^2^+5.0042P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2159 _refine_ls_number_parameters 199 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.0821 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.235 _refine_ls_restrained_S_all 1.233 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Tb1 Tb 1.04785(4) 0.12630(3) 0.50629(4) 0.01589(14) Uani 1 1 d . . . C1 C 0.6841(9) 0.0911(5) -0.0136(9) 0.0154(19) Uani 1 1 d U . . C2 C 0.6768(9) 0.1333(6) 0.1229(9) 0.0181(18) Uani 1 1 d . . . C3 C 0.5368(10) 0.1703(6) 0.1383(9) 0.023(2) Uani 1 1 d . . . H3 H 0.5286 0.1970 0.2292 0.027 Uiso 1 1 calc R . . C4 C 0.4120(10) 0.1679(6) 0.0229(10) 0.022(2) Uani 1 1 d U . . H4 H 0.3206 0.1934 0.0343 0.026 Uiso 1 1 calc R . . C5 C 0.4257(9) 0.1263(6) -0.1123(8) 0.0172(17) Uani 1 1 d . . . C6 C 0.5606(9) 0.0868(5) -0.1291(9) 0.0189(19) Uani 1 1 d . . . H6 H 0.5671 0.0576 -0.2182 0.023 Uiso 1 1 calc R . . C7 C 0.8052(10) 0.1380(6) 0.2532(10) 0.020(2) Uani 1 1 d . . . C8 C 0.2919(9) 0.1259(7) -0.2432(9) 0.0216(19) Uani 1 1 d . . . C9 C 0.8341(11) 0.0018(6) -0.1508(10) 0.024(2) Uani 1 1 d . . . H9A H 0.7357 -0.0235 -0.1910 0.029 Uiso 1 1 calc R . . H9B H 0.9046 -0.0446 -0.1180 0.029 Uiso 1 1 calc R . . C10 C 0.8881(9) 0.0489(5) -0.2769(10) 0.0180(19) Uani 1 1 d . . . O1 O 0.9390(7) 0.1502(4) 0.2345(6) 0.0201(14) Uani 1 1 d . . . O2 O 0.7806(6) 0.1312(4) 0.3879(6) 0.0263(14) Uani 1 1 d . . . O3 O 0.9251(7) 0.0061(3) -0.3835(6) 0.0161(13) Uani 1 1 d . . . O4 O 0.9103(7) 0.1269(4) -0.2691(6) 0.0273(14) Uani 1 1 d . . . O5 O 0.2143(7) 0.1931(4) -0.2724(7) 0.0246(15) Uani 1 1 d . . . O6 O 0.2612(7) 0.0608(4) -0.3236(7) 0.0278(16) Uani 1 1 d . . . O7 O 0.8198(6) 0.0514(4) -0.0221(6) 0.0265(15) Uani 1 1 d . . . O8 O 1.2529(7) 0.1590(4) 0.3860(7) 0.0254(15) Uani 1 1 d . . . O9 O 1.0060(7) 0.2739(4) 0.4885(6) 0.0235(14) Uani 1 1 d . . . O10 O 0.535(3) 0.1121(14) 0.506(3) 0.053(6) Uani 0.50 1 d P . . O10' O 0.521(4) 0.0675(13) 0.469(3) 0.050(7) Uani 0.50 1 d P . . 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 0.0135(2) 0.0192(2) 0.0139(2) -0.0005(2) -0.00023(14) 0.0004(2) C1 0.013(3) 0.019(3) 0.017(4) 0.001(3) 0.008(3) 0.005(3) C2 0.013(4) 0.020(5) 0.018(4) 0.001(4) -0.005(3) 0.003(4) C3 0.024(5) 0.032(5) 0.009(4) 0.000(4) -0.002(4) 0.009(4) C4 0.016(4) 0.027(4) 0.022(4) 0.001(3) 0.000(3) 0.007(3) C5 0.014(4) 0.027(5) 0.009(4) 0.005(4) -0.001(3) -0.003(4) C6 0.017(5) 0.028(5) 0.011(4) -0.004(4) 0.000(4) 0.003(4) C7 0.017(5) 0.019(5) 0.021(5) -0.001(4) -0.006(4) 0.005(4) C8 0.019(4) 0.035(5) 0.010(4) -0.005(5) -0.001(3) -0.002(5) C9 0.024(5) 0.026(5) 0.024(5) -0.009(4) 0.004(4) 0.008(4) C10 0.008(4) 0.023(5) 0.022(5) 0.002(4) 0.003(4) -0.003(4) O1 0.016(3) 0.030(4) 0.014(3) 0.001(2) 0.000(2) -0.004(3) O2 0.012(3) 0.047(4) 0.020(3) 0.001(3) 0.002(2) -0.002(3) O3 0.023(3) 0.016(3) 0.010(3) -0.005(2) 0.006(3) 0.000(2) O4 0.037(4) 0.021(3) 0.024(3) -0.006(3) 0.008(3) -0.006(4) O5 0.024(4) 0.025(4) 0.021(3) 0.001(3) -0.005(3) 0.009(3) O6 0.026(4) 0.023(4) 0.029(4) -0.005(3) -0.010(3) 0.003(3) O7 0.016(3) 0.047(4) 0.017(3) -0.009(3) 0.003(3) 0.007(3) O8 0.022(3) 0.027(3) 0.028(4) 0.004(3) 0.005(3) -0.005(3) O9 0.027(4) 0.024(3) 0.018(3) 0.000(3) 0.002(3) 0.009(3) O10 0.034(10) 0.072(16) 0.057(15) 0.043(16) 0.015(10) 0.026(17) O10' 0.041(12) 0.049(13) 0.068(16) 0.015(13) 0.029(11) 0.015(14) _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 O9 2.342(6) . ? Tb1 O8 2.343(6) . ? Tb1 O3 2.380(5) 3_755 ? Tb1 O2 2.425(5) . ? Tb1 O6 2.435(6) 1_656 ? Tb1 O3 2.472(5) 1_556 ? Tb1 O1 2.476(5) . ? Tb1 O5 2.478(6) 1_656 ? Tb1 O4 2.540(6) 1_556 ? Tb1 C8 2.824(8) 1_656 ? Tb1 C10 2.877(8) 1_556 ? C1 C6 1.366(11) . ? C1 O7 1.375(9) . ? C1 C2 1.401(11) . ? C2 C3 1.405(12) . ? C2 C7 1.478(11) . ? C3 C4 1.373(12) . ? C4 C5 1.399(12) . ? C5 C6 1.385(11) . ? C5 C8 1.511(10) . ? C7 O1 1.249(10) . ? C7 O2 1.269(10) . ? C8 O6 1.249(11) . ? C8 O5 1.260(11) . ? C8 Tb1 2.824(8) 1_454 ? C9 O7 1.415(10) . ? C9 C10 1.501(12) . ? C10 O4 1.237(10) . ? C10 O3 1.258(10) . ? C10 Tb1 2.877(8) 1_554 ? O3 Tb1 2.380(5) 3_755 ? O3 Tb1 2.472(5) 1_554 ? O4 Tb1 2.540(6) 1_554 ? O5 Tb1 2.478(6) 1_454 ? O6 Tb1 2.435(6) 1_454 ? O10 O10' 0.77(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 Tb1 O8 83.2(2) . . ? O9 Tb1 O3 148.97(19) . 3_755 ? O8 Tb1 O3 79.9(2) . 3_755 ? O9 Tb1 O2 78.9(2) . . ? O8 Tb1 O2 125.4(2) . . ? O3 Tb1 O2 90.0(2) 3_755 . ? O9 Tb1 O6 123.7(2) . 1_656 ? O8 Tb1 O6 78.1(2) . 1_656 ? O3 Tb1 O6 77.8(2) 3_755 1_656 ? O2 Tb1 O6 151.5(2) . 1_656 ? O9 Tb1 O3 134.6(2) . 1_556 ? O8 Tb1 O3 142.2(2) . 1_556 ? O3 Tb1 O3 67.1(2) 3_755 1_556 ? O2 Tb1 O3 74.1(2) . 1_556 ? O6 Tb1 O3 77.4(2) 1_656 1_556 ? O9 Tb1 O1 75.83(19) . . ? O8 Tb1 O1 73.4(2) . . ? O3 Tb1 O1 74.50(18) 3_755 . ? O2 Tb1 O1 52.36(19) . . ? O6 Tb1 O1 143.0(2) 1_656 . ? O3 Tb1 O1 112.62(18) 1_556 . ? O9 Tb1 O5 72.7(2) . 1_656 ? O8 Tb1 O5 82.6(2) . 1_656 ? O3 Tb1 O5 129.82(19) 3_755 1_656 ? O2 Tb1 O5 137.1(2) . 1_656 ? O6 Tb1 O5 52.64(19) 1_656 1_656 ? O3 Tb1 O5 104.27(19) 1_556 1_656 ? O1 Tb1 O5 142.24(19) . 1_656 ? O9 Tb1 O4 87.5(2) . 1_556 ? O8 Tb1 O4 153.4(2) . 1_556 ? O3 Tb1 O4 118.25(19) 3_755 1_556 ? O2 Tb1 O4 76.53(19) . 1_556 ? O6 Tb1 O4 86.7(2) 1_656 1_556 ? O3 Tb1 O4 51.19(18) 1_556 1_556 ? O1 Tb1 O4 128.13(18) . 1_556 ? O5 Tb1 O4 70.81(19) 1_656 1_556 ? O9 Tb1 C8 98.4(3) . 1_656 ? O8 Tb1 C8 79.2(2) . 1_656 ? O3 Tb1 C8 103.7(2) 3_755 1_656 ? O2 Tb1 C8 154.1(2) . 1_656 ? O6 Tb1 C8 26.2(2) 1_656 1_656 ? O3 Tb1 C8 90.9(2) 1_556 1_656 ? O1 Tb1 C8 152.4(2) . 1_656 ? O5 Tb1 C8 26.5(2) 1_656 1_656 ? O4 Tb1 C8 77.6(2) 1_556 1_656 ? O9 Tb1 C10 111.7(2) . 1_556 ? O8 Tb1 C10 158.0(2) . 1_556 ? O3 Tb1 C10 92.8(2) 3_755 1_556 ? O2 Tb1 C10 74.9(2) . 1_556 ? O6 Tb1 C10 80.1(2) 1_656 1_556 ? O3 Tb1 C10 25.8(2) 1_556 1_556 ? O1 Tb1 C10 124.9(2) . 1_556 ? O5 Tb1 C10 86.4(2) 1_656 1_556 ? O4 Tb1 C10 25.4(2) 1_556 1_556 ? C8 Tb1 C10 82.5(2) 1_656 1_556 ? C6 C1 O7 122.1(7) . . ? C6 C1 C2 121.5(8) . . ? O7 C1 C2 116.3(7) . . ? C1 C2 C3 117.6(7) . . ? C1 C2 C7 123.9(8) . . ? C3 C2 C7 118.4(7) . . ? C4 C3 C2 121.8(8) . . ? C3 C4 C5 118.4(8) . . ? C6 C5 C4 121.1(7) . . ? C6 C5 C8 119.5(7) . . ? C4 C5 C8 119.4(8) . . ? C1 C6 C5 119.4(8) . . ? O1 C7 O2 118.4(7) . . ? O1 C7 C2 121.5(8) . . ? O2 C7 C2 120.1(8) . . ? O6 C8 O5 120.5(7) . . ? O6 C8 C5 120.5(9) . . ? O5 C8 C5 118.9(8) . . ? O6 C8 Tb1 59.2(4) . 1_454 ? O5 C8 Tb1 61.3(4) . 1_454 ? C5 C8 Tb1 178.3(6) . 1_454 ? O7 C9 C10 115.6(7) . . ? O4 C10 O3 120.5(8) . . ? O4 C10 C9 120.9(8) . . ? O3 C10 C9 118.3(7) . . ? O4 C10 Tb1 61.9(4) . 1_554 ? O3 C10 Tb1 58.8(4) . 1_554 ? C9 C10 Tb1 169.1(6) . 1_554 ? C7 O1 Tb1 93.3(5) . . ? C7 O2 Tb1 95.2(5) . . ? C10 O3 Tb1 151.3(5) . 3_755 ? C10 O3 Tb1 95.4(5) . 1_554 ? Tb1 O3 Tb1 112.9(2) 3_755 1_554 ? C10 O4 Tb1 92.7(5) . 1_554 ? C8 O5 Tb1 92.2(5) . 1_454 ? C8 O6 Tb1 94.6(5) . 1_454 ? C1 O7 C9 120.3(7) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.019 _refine_diff_density_min -1.076 _refine_diff_density_rms 0.166 data_9 _database_code_depnum_ccdc_archive 'CCDC 906617' #TrackingRef '906617.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H11 O10 Yb' _chemical_formula_weight 464.23 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' Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8839(5) _cell_length_b 15.4942(11) _cell_length_c 8.8941(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.575(6) _cell_angle_gamma 90.00 _cell_volume 1203.47(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1085 _cell_measurement_theta_min 2.5105 _cell_measurement_theta_max 28.7933 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 2.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 884 _exptl_absorpt_coefficient_mu 7.826 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4798 _exptl_absorpt_correction_T_max 0.5083 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.2116 _diffrn_standards_number 3908 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4816 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2138 _reflns_number_gt 1666 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET) (compiled Sep 15 2009,11:49:04) ; _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^)+(0.0358P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2138 _refine_ls_number_parameters 199 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0266 _refine_ls_wR_factor_ref 0.0702 _refine_ls_wR_factor_gt 0.0679 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.047 _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 Yb1 Yb 1.04631(3) 0.12559(2) 0.50698(3) 0.00770(11) Uani 1 1 d . . . C1 C 0.6834(7) 0.0888(4) 0.9871(6) 0.0057(13) Uani 1 1 d U . . C2 C 0.6743(7) 0.1336(4) 1.1262(7) 0.0079(13) Uani 1 1 d U . . C3 C 0.5360(7) 0.1704(4) 1.1421(7) 0.0084(14) Uani 1 1 d . . . H3 H 0.5280 0.1973 1.2338 0.010 Uiso 1 1 calc R . . C4 C 0.4091(7) 0.1683(5) 1.0254(7) 0.0103(14) Uani 1 1 d . . . H4 H 0.3184 0.1950 1.0374 0.012 Uiso 1 1 calc R . . C5 C 0.4195(7) 0.1252(5) 0.8886(7) 0.0078(13) Uani 1 1 d U . . C6 C 0.5560(7) 0.0853(4) 0.8721(7) 0.0077(13) Uani 1 1 d U . . H6 H 0.5615 0.0559 0.7822 0.009 Uiso 1 1 calc R . . C7 C 0.8345(8) -0.0011(4) 0.8489(7) 0.0099(14) Uani 1 1 d . . . H7A H 0.7356 -0.0263 0.8076 0.012 Uiso 1 1 calc R . . H7B H 0.9053 -0.0480 0.8818 0.012 Uiso 1 1 calc R . . C8 C 0.8904(7) 0.0492(4) 0.7242(6) 0.0069(14) Uani 1 1 d . . . C9 C 0.8064(7) 0.1370(4) 1.2573(7) 0.0092(14) Uani 1 1 d U . . C10 C 0.2858(7) 0.1258(5) 0.7562(7) 0.0074(13) Uani 1 1 d U . . O1 O 0.8204(5) 0.0512(3) 0.9800(4) 0.0112(10) Uani 1 1 d U . . O2 O 0.9101(5) 0.1287(3) 0.7299(5) 0.0119(10) Uani 1 1 d . . . O3 O 0.9278(4) 0.0062(3) 0.6140(4) 0.0050(9) Uani 1 1 d U . . O4 O 0.9415(5) 0.1498(3) 1.2365(5) 0.0102(10) Uani 1 1 d . . . O5 O 0.7827(5) 0.1301(3) 1.3936(4) 0.0122(10) Uani 1 1 d . . . O6 O 0.2110(5) 0.1953(3) 0.7266(4) 0.0121(11) Uani 1 1 d . . . O7 O 0.2537(5) 0.0597(3) 0.6770(5) 0.0149(11) Uani 1 1 d . . . O8 O 1.2486(5) 0.1565(3) 0.3931(5) 0.0115(10) Uani 1 1 d . . . H8A H 1.3388 0.1378 0.4272 0.014 Uiso 1 1 d R . . H8B H 1.2410 0.2090 0.3639 0.014 Uiso 1 1 d R . . O9 O 1.0057(5) 0.2706(3) 0.4897(4) 0.0099(10) Uani 1 1 d U . . H9A H 0.9836 0.3032 0.5636 0.012 Uiso 1 1 d R . . H9B H 0.9693 0.2947 0.4024 0.012 Uiso 1 1 d R . . O10 O 0.5396(11) 0.1138(9) 0.5141(11) 0.025(3) Uani 0.50 1 d P . . O10' O 0.5162(14) 0.0673(8) 0.4729(12) 0.023(3) Uani 0.50 1 d PU . . 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 Yb1 0.00749(16) 0.00852(17) 0.00711(16) 0.00017(13) 0.00137(10) 0.00019(14) C1 0.0057(15) 0.0060(16) 0.0057(15) 0.0009(10) 0.0019(10) 0.0000(10) C2 0.0083(16) 0.0077(16) 0.0075(15) 0.0007(10) 0.0012(10) -0.0004(10) C3 0.014(3) 0.006(4) 0.005(3) -0.002(3) 0.000(3) 0.004(3) C4 0.007(3) 0.012(4) 0.013(3) -0.001(3) 0.003(3) 0.003(3) C5 0.0080(15) 0.0074(16) 0.0079(15) 0.0002(10) 0.0014(10) -0.0003(10) C6 0.0080(16) 0.0075(16) 0.0078(16) -0.0003(10) 0.0020(10) 0.0002(10) C7 0.015(3) 0.011(4) 0.005(3) -0.003(3) 0.005(3) -0.001(3) C8 0.006(3) 0.007(4) 0.007(3) 0.000(3) -0.001(2) -0.004(3) C9 0.0092(16) 0.0086(17) 0.0094(16) -0.0004(10) 0.0010(10) 0.0003(10) C10 0.0074(15) 0.0083(16) 0.0068(15) 0.0000(10) 0.0023(10) -0.0001(10) O1 0.0110(13) 0.0122(13) 0.0109(12) -0.0014(9) 0.0030(9) 0.0010(9) O2 0.021(2) 0.010(3) 0.006(2) -0.001(2) 0.0051(18) -0.003(3) O3 0.0056(12) 0.0057(13) 0.0041(12) -0.0002(9) 0.0023(9) 0.0005(9) O4 0.009(2) 0.012(3) 0.009(2) -0.0002(19) 0.0011(18) 0.001(2) O5 0.011(2) 0.018(3) 0.008(2) 0.001(2) 0.0017(18) -0.007(2) O6 0.009(2) 0.015(3) 0.010(2) 0.000(2) -0.0011(18) 0.002(2) O7 0.016(3) 0.012(3) 0.014(2) 0.000(2) -0.0029(19) 0.002(2) O8 0.010(2) 0.006(2) 0.019(2) 0.001(2) 0.0040(19) 0.001(2) O9 0.0119(12) 0.0099(13) 0.0080(12) -0.0004(9) 0.0022(9) 0.0010(9) O10 0.012(5) 0.042(9) 0.021(6) 0.008(6) 0.004(4) 0.012(6) O10' 0.023(3) 0.023(3) 0.023(3) -0.0002(10) 0.0043(12) 0.0003(10) _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 Yb1 O8 2.270(4) . ? Yb1 O9 2.277(5) . ? Yb1 O3 2.339(4) 3_756 ? Yb1 O5 2.374(4) 1_554 ? Yb1 O7 2.387(5) 1_655 ? Yb1 O3 2.409(4) . ? Yb1 O4 2.444(4) 1_554 ? Yb1 O6 2.464(4) 1_655 ? Yb1 O2 2.506(4) . ? Yb1 C10 2.776(6) 1_655 ? Yb1 C9 2.787(6) 1_554 ? Yb1 Yb1 3.9750(7) 3_756 ? Yb1 H8B 2.6625 . ? C1 O1 1.361(7) . ? C1 C6 1.380(9) . ? C1 C2 1.434(8) . ? C2 C3 1.385(9) . ? C2 C9 1.496(9) . ? C3 C4 1.385(9) . ? C3 H3 0.9300 . ? C4 C5 1.406(9) . ? C4 H4 0.9300 . ? C5 C6 1.393(9) . ? C5 C10 1.511(8) . ? C6 H6 0.9300 . ? C7 O1 1.444(7) . ? C7 C8 1.512(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O2 1.244(7) . ? C8 O3 1.278(7) . ? C9 O4 1.263(7) . ? C9 O5 1.273(7) . ? C9 Yb1 2.787(6) 1_556 ? C10 O7 1.247(8) . ? C10 O6 1.267(8) . ? C10 Yb1 2.776(6) 1_455 ? O3 Yb1 2.339(4) 3_756 ? O4 Yb1 2.444(4) 1_556 ? O5 Yb1 2.374(4) 1_556 ? O6 Yb1 2.464(4) 1_455 ? O7 Yb1 2.387(5) 1_455 ? O8 H8A 0.8536 . ? O8 H8B 0.8533 . ? O9 H9A 0.8788 . ? O9 H9B 0.8687 . ? O10 O10' 0.818(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Yb1 O9 83.71(15) . . ? O8 Yb1 O3 79.99(15) . 3_756 ? O9 Yb1 O3 149.15(13) . 3_756 ? O8 Yb1 O5 127.17(14) . 1_554 ? O9 Yb1 O5 79.09(16) . 1_554 ? O3 Yb1 O5 90.16(15) 3_756 1_554 ? O8 Yb1 O7 77.92(16) . 1_655 ? O9 Yb1 O7 124.00(16) . 1_655 ? O3 Yb1 O7 77.77(15) 3_756 1_655 ? O5 Yb1 O7 150.18(16) 1_554 1_655 ? O8 Yb1 O3 141.02(15) . . ? O9 Yb1 O3 135.16(14) . . ? O3 Yb1 O3 66.32(15) 3_756 . ? O5 Yb1 O3 73.84(14) 1_554 . ? O7 Yb1 O3 76.34(15) 1_655 . ? O8 Yb1 O4 73.63(15) . 1_554 ? O9 Yb1 O4 75.81(14) . 1_554 ? O3 Yb1 O4 74.54(14) 3_756 1_554 ? O5 Yb1 O4 53.82(14) 1_554 1_554 ? O7 Yb1 O4 143.07(15) 1_655 1_554 ? O3 Yb1 O4 113.05(14) . 1_554 ? O8 Yb1 O6 81.83(14) . 1_655 ? O9 Yb1 O6 71.61(15) . 1_655 ? O3 Yb1 O6 130.76(14) 3_756 1_655 ? O5 Yb1 O6 136.01(15) 1_554 1_655 ? O7 Yb1 O6 53.75(16) 1_655 1_655 ? O3 Yb1 O6 105.21(14) . 1_655 ? O4 Yb1 O6 140.92(15) 1_554 1_655 ? O8 Yb1 O2 152.36(15) . . ? O9 Yb1 O2 86.61(14) . . ? O3 Yb1 O2 118.89(14) 3_756 . ? O5 Yb1 O2 75.74(14) 1_554 . ? O7 Yb1 O2 86.31(15) 1_655 . ? O3 Yb1 O2 52.59(14) . . ? O4 Yb1 O2 128.60(14) 1_554 . ? O6 Yb1 O2 70.55(14) 1_655 . ? O8 Yb1 C10 78.62(16) . 1_655 ? O9 Yb1 C10 98.12(18) . 1_655 ? O3 Yb1 C10 104.05(17) 3_756 1_655 ? O5 Yb1 C10 152.92(15) 1_554 1_655 ? O7 Yb1 C10 26.61(18) 1_655 1_655 ? O3 Yb1 C10 90.69(17) . 1_655 ? O4 Yb1 C10 152.05(16) 1_554 1_655 ? O6 Yb1 C10 27.15(17) 1_655 1_655 ? O2 Yb1 C10 77.21(16) . 1_655 ? O8 Yb1 C9 100.57(16) . 1_554 ? O9 Yb1 C9 78.17(18) . 1_554 ? O3 Yb1 C9 79.31(17) 3_756 1_554 ? O5 Yb1 C9 27.06(15) 1_554 1_554 ? O7 Yb1 C9 156.93(17) 1_655 1_554 ? O3 Yb1 C9 92.16(16) . 1_554 ? O4 Yb1 C9 26.93(16) 1_554 1_554 ? O6 Yb1 C9 149.27(17) 1_655 1_554 ? O2 Yb1 C9 102.68(16) . 1_554 ? C10 Yb1 C9 176.3(2) 1_655 1_554 ? O8 Yb1 Yb1 111.64(12) . 3_756 ? O9 Yb1 Yb1 159.22(11) . 3_756 ? O3 Yb1 Yb1 33.71(9) 3_756 3_756 ? O5 Yb1 Yb1 80.39(12) 1_554 3_756 ? O7 Yb1 Yb1 74.47(12) 1_655 3_756 ? O3 Yb1 Yb1 32.61(9) . 3_756 ? O4 Yb1 Yb1 94.61(10) 1_554 3_756 ? O6 Yb1 Yb1 122.91(11) 1_655 3_756 ? O2 Yb1 Yb1 85.20(10) . 3_756 ? C10 Yb1 Yb1 98.64(15) 1_655 3_756 ? C9 Yb1 Yb1 85.04(14) 1_554 3_756 ? O8 Yb1 H8B 17.7 . . ? O9 Yb1 H8B 66.3 . . ? O3 Yb1 H8B 94.4 3_756 . ? O5 Yb1 H8B 117.4 1_554 . ? O7 Yb1 H8B 91.0 1_655 . ? O3 Yb1 H8B 158.6 . . ? O4 Yb1 H8B 67.6 1_554 . ? O6 Yb1 H8B 79.8 1_655 . ? O2 Yb1 H8B 145.0 . . ? C10 Yb1 H8B 84.9 1_655 . ? C9 Yb1 H8B 93.3 1_554 . ? Yb1 Yb1 H8B 127.5 3_756 . ? O1 C1 C6 124.6(5) . . ? O1 C1 C2 116.1(5) . . ? C6 C1 C2 119.3(6) . . ? C3 C2 C1 118.6(6) . . ? C3 C2 C9 119.3(5) . . ? C1 C2 C9 122.0(6) . . ? C2 C3 C4 121.9(6) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C3 C4 C5 119.1(6) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C6 C5 C4 119.9(6) . . ? C6 C5 C10 119.8(5) . . ? C4 C5 C10 120.3(6) . . ? C1 C6 C5 121.1(6) . . ? C1 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? O1 C7 C8 113.0(5) . . ? O1 C7 H7A 109.0 . . ? C8 C7 H7A 109.0 . . ? O1 C7 H7B 109.0 . . ? C8 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? O2 C8 O3 119.5(5) . . ? O2 C8 C7 122.9(5) . . ? O3 C8 C7 117.4(5) . . ? O4 C9 O5 118.7(6) . . ? O4 C9 C2 121.5(5) . . ? O5 C9 C2 119.8(5) . . ? O4 C9 Yb1 61.2(3) . 1_556 ? O5 C9 Yb1 58.1(3) . 1_556 ? C2 C9 Yb1 174.1(5) . 1_556 ? O7 C10 O6 121.6(6) . . ? O7 C10 C5 120.1(6) . . ? O6 C10 C5 118.3(6) . . ? O7 C10 Yb1 59.0(3) . 1_455 ? O6 C10 Yb1 62.6(3) . 1_455 ? C5 C10 Yb1 178.2(4) . 1_455 ? C1 O1 C7 119.2(5) . . ? C8 O2 Yb1 91.9(3) . . ? C8 O3 Yb1 150.3(4) . 3_756 ? C8 O3 Yb1 95.6(4) . . ? Yb1 O3 Yb1 113.68(15) 3_756 . ? C9 O4 Yb1 91.8(3) . 1_556 ? C9 O5 Yb1 94.8(4) . 1_556 ? C10 O6 Yb1 90.3(4) . 1_455 ? C10 O7 Yb1 94.4(4) . 1_455 ? Yb1 O8 H8A 122.6 . . ? Yb1 O8 H8B 108.2 . . ? H8A O8 H8B 116.6 . . ? Yb1 O9 H9A 124.8 . . ? Yb1 O9 H9B 120.8 . . ? H9A O9 H9B 108.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -177.7(6) . . . . ? C6 C1 C2 C3 1.5(10) . . . . ? O1 C1 C2 C9 -1.4(9) . . . . ? C6 C1 C2 C9 177.8(6) . . . . ? C1 C2 C3 C4 -2.9(10) . . . . ? C9 C2 C3 C4 -179.2(6) . . . . ? C2 C3 C4 C5 2.1(11) . . . . ? C3 C4 C5 C6 0.1(10) . . . . ? C3 C4 C5 C10 -176.8(6) . . . . ? O1 C1 C6 C5 179.7(6) . . . . ? C2 C1 C6 C5 0.6(10) . . . . ? C4 C5 C6 C1 -1.4(10) . . . . ? C10 C5 C6 C1 175.5(6) . . . . ? O1 C7 C8 O2 -5.3(9) . . . . ? O1 C7 C8 O3 170.0(5) . . . . ? C3 C2 C9 O4 -141.1(6) . . . . ? C1 C2 C9 O4 42.6(10) . . . . ? C3 C2 C9 O5 36.3(10) . . . . ? C1 C2 C9 O5 -140.0(6) . . . . ? C3 C2 C9 Yb1 103(4) . . . 1_556 ? C1 C2 C9 Yb1 -73(4) . . . 1_556 ? C6 C5 C10 O7 41.9(9) . . . . ? C4 C5 C10 O7 -141.2(6) . . . . ? C6 C5 C10 O6 -136.4(6) . . . . ? C4 C5 C10 O6 40.5(9) . . . . ? C6 C5 C10 Yb1 -17(17) . . . 1_455 ? C4 C5 C10 Yb1 160(16) . . . 1_455 ? C6 C1 O1 C7 -4.4(9) . . . . ? C2 C1 O1 C7 174.8(5) . . . . ? C8 C7 O1 C1 92.8(6) . . . . ? O3 C8 O2 Yb1 -6.3(6) . . . . ? C7 C8 O2 Yb1 168.9(6) . . . . ? O8 Yb1 O2 C8 -126.8(4) . . . . ? O9 Yb1 O2 C8 163.6(4) . . . . ? O3 Yb1 O2 C8 1.9(4) 3_756 . . . ? O5 Yb1 O2 C8 84.0(4) 1_554 . . . ? O7 Yb1 O2 C8 -72.0(4) 1_655 . . . ? O3 Yb1 O2 C8 3.7(3) . . . . ? O4 Yb1 O2 C8 94.8(4) 1_554 . . . ? O6 Yb1 O2 C8 -124.7(4) 1_655 . . . ? C10 Yb1 O2 C8 -97.2(4) 1_655 . . . ? C9 Yb1 O2 C8 86.6(4) 1_554 . . . ? Yb1 Yb1 O2 C8 2.8(4) 3_756 . . . ? O2 C8 O3 Yb1 176.8(5) . . . 3_756 ? C7 C8 O3 Yb1 1.3(11) . . . 3_756 ? O2 C8 O3 Yb1 6.6(6) . . . . ? C7 C8 O3 Yb1 -168.9(5) . . . . ? O8 Yb1 O3 C8 142.3(4) . . . . ? O9 Yb1 O3 C8 -32.6(4) . . . . ? O3 Yb1 O3 C8 174.7(4) 3_756 . . . ? O5 Yb1 O3 C8 -87.8(4) 1_554 . . . ? O7 Yb1 O3 C8 92.3(4) 1_655 . . . ? O4 Yb1 O3 C8 -125.4(3) 1_554 . . . ? O6 Yb1 O3 C8 46.5(4) 1_655 . . . ? O2 Yb1 O3 C8 -3.6(3) . . . . ? C10 Yb1 O3 C8 69.7(4) 1_655 . . . ? C9 Yb1 O3 C8 -107.9(4) 1_554 . . . ? Yb1 Yb1 O3 C8 174.7(4) 3_756 . . . ? O8 Yb1 O3 Yb1 -32.4(3) . . . 3_756 ? O9 Yb1 O3 Yb1 152.68(17) . . . 3_756 ? O3 Yb1 O3 Yb1 0.0 3_756 . . 3_756 ? O5 Yb1 O3 Yb1 97.49(19) 1_554 . . 3_756 ? O7 Yb1 O3 Yb1 -82.44(18) 1_655 . . 3_756 ? O4 Yb1 O3 Yb1 59.8(2) 1_554 . . 3_756 ? O6 Yb1 O3 Yb1 -128.29(17) 1_655 . . 3_756 ? O2 Yb1 O3 Yb1 -178.3(3) . . . 3_756 ? C10 Yb1 O3 Yb1 -105.1(2) 1_655 . . 3_756 ? C9 Yb1 O3 Yb1 77.33(19) 1_554 . . 3_756 ? O5 C9 O4 Yb1 8.7(6) . . . 1_556 ? C2 C9 O4 Yb1 -173.9(6) . . . 1_556 ? O4 C9 O5 Yb1 -9.0(6) . . . 1_556 ? C2 C9 O5 Yb1 173.6(6) . . . 1_556 ? O7 C10 O6 Yb1 0.0(6) . . . 1_455 ? C5 C10 O6 Yb1 178.3(5) . . . 1_455 ? O6 C10 O7 Yb1 0.0(6) . . . 1_455 ? C5 C10 O7 Yb1 -178.2(5) . . . 1_455 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.926 _refine_diff_density_min -0.690 _refine_diff_density_rms 0.182