Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Linpei Jin' _publ_contact_author_address ; Department of Chemistry Beijing Normal University Beijing 100875 CHINA ; _publ_contact_author_email LPJIN@BNU.EDU.CN _publ_section_title ; Low pH hydrothermal synthesis and properties of lanthanide-organic frameworks with (4^10,6^5)(4^9,6^6) topology constructed from Ln-Hbptc building block ; loop_ _publ_author_name 'Linpei Jin.' 'Licun Li.' 'Danfeng Weng.' 'Wenwen Yang.' 'Xianjun Zheng.' # Attachment 'Eu_complex.cif' data_r60604e _database_code_depnum_ccdc_archive 'CCDC 628276' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H9 Eu O9' _chemical_formula_sum 'C16 H9 Eu O9' _chemical_formula_weight 497.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 13.030(6) _cell_length_b 6.715(3) _cell_length_c 16.385(8) _cell_angle_alpha 90.00 _cell_angle_beta 108.600(3) _cell_angle_gamma 90.00 _cell_volume 1358.7(10) _cell_formula_units_Z 4 _cell_measurement_temperature 294 _cell_measurement_reflns_used 3307 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 27.9 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 4.676 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6038 _exptl_absorpt_correction_T_max 0.7667 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10064 _diffrn_reflns_av_R_equivalents 0.0583 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.65 _diffrn_reflns_theta_max 27.85 _reflns_number_total 3224 _reflns_number_gt 2792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^+4.3336P] 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 SHELXL _refine_ls_extinction_coef 0.00056(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3224 _refine_ls_number_parameters 249 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.0858 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Eu1 Eu 0.47056(2) 0.18636(4) 0.093352(18) 0.01199(10) Uani 1 1 d . . . O1 O 0.3753(3) 0.2896(6) 0.1872(3) 0.0179(9) Uani 1 1 d . . . O2 O 0.4212(3) 0.5546(6) 0.2719(2) 0.0157(8) Uani 1 1 d . . . O3 O 0.4231(3) 0.3753(6) 0.4275(3) 0.0177(9) Uani 1 1 d . . . O4 O 0.2931(3) 0.3741(6) 0.4865(3) 0.0192(9) Uani 1 1 d . . . O5 O -0.2584(3) 0.1227(7) -0.1946(3) 0.0233(10) Uani 1 1 d . . . O6 O -0.3798(3) 0.1241(6) -0.1252(3) 0.0184(9) Uani 1 1 d . . . O7 O -0.3892(3) 0.5091(6) -0.0326(3) 0.0245(10) Uani 1 1 d . . . O8 O -0.3716(3) 0.2762(6) 0.0660(3) 0.0184(9) Uani 1 1 d . . . O9 O 0.5630(3) 0.4932(6) 0.1783(3) 0.0194(9) Uani 1 1 d D . . C1 C 0.2517(4) 0.3912(8) 0.2553(4) 0.0127(11) Uani 1 1 d . . . C2 C 0.2347(4) 0.3883(8) 0.3353(4) 0.0140(11) Uani 1 1 d . . . C3 C 0.1281(4) 0.3750(10) 0.3356(4) 0.0205(13) Uani 1 1 d . . . H3 H 0.1150 0.3749 0.3882 0.025 Uiso 1 1 calc R . . C4 C 0.0407(5) 0.3620(10) 0.2604(4) 0.0215(13) Uani 1 1 d . . . H4 H -0.0294 0.3553 0.2632 0.026 Uiso 1 1 calc R . . C5 C 0.0579(4) 0.3591(9) 0.1806(4) 0.0155(12) Uani 1 1 d . . . C6 C 0.1643(4) 0.3737(9) 0.1805(4) 0.0170(12) Uani 1 1 d . . . H6 H 0.1774 0.3717 0.1279 0.020 Uiso 1 1 calc R . . C7 C 0.3591(4) 0.4133(9) 0.2391(3) 0.0125(11) Uani 1 1 d . . . C8 C 0.3221(4) 0.3834(9) 0.4215(4) 0.0168(12) Uani 1 1 d . . . C9 C -0.2007(4) 0.2400(9) -0.0533(4) 0.0183(12) Uani 1 1 d . . . C10 C -0.2244(4) 0.3277(8) 0.0160(4) 0.0143(11) Uani 1 1 d . . . C11 C -0.1397(4) 0.3707(8) 0.0917(4) 0.0175(12) Uani 1 1 d . . . H11 H -0.1554 0.4266 0.1383 0.021 Uiso 1 1 calc R . . C12 C -0.0318(4) 0.3307(9) 0.0982(4) 0.0170(12) Uani 1 1 d . . . C13 C -0.0108(4) 0.2546(10) 0.0264(4) 0.0209(13) Uani 1 1 d . . . H13 H 0.0606 0.2349 0.0284 0.025 Uiso 1 1 calc R . . C14 C -0.0937(5) 0.2072(9) -0.0482(4) 0.0209(13) Uani 1 1 d . . . H14 H -0.0775 0.1533 -0.0950 0.025 Uiso 1 1 calc R . . C15 C -0.2888(4) 0.1587(8) -0.1277(4) 0.0147(12) Uani 1 1 d . . . C16 C -0.3376(4) 0.3743(8) 0.0154(4) 0.0133(11) Uani 1 1 d . . . H9B H 0.564(6) 0.588(8) 0.144(4) 0.06(3) Uiso 1 1 d D . . H9A H 0.513(5) 0.509(11) 0.200(5) 0.06(3) Uiso 1 1 d D . . H1 H -0.308(6) 0.071(13) -0.237(6) 0.05(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Eu1 0.01060(15) 0.01522(17) 0.00952(16) 0.00032(12) 0.00230(10) 0.00105(10) O1 0.020(2) 0.021(2) 0.015(2) -0.0047(18) 0.0084(16) -0.0007(17) O2 0.0110(17) 0.021(2) 0.014(2) -0.0002(17) 0.0016(15) -0.0033(16) O3 0.0097(18) 0.026(2) 0.015(2) 0.0019(18) 0.0014(15) -0.0002(16) O4 0.021(2) 0.025(2) 0.011(2) -0.0019(17) 0.0032(16) 0.0032(17) O5 0.019(2) 0.036(3) 0.013(2) -0.004(2) 0.0023(17) -0.0046(19) O6 0.0148(19) 0.021(2) 0.017(2) 0.0007(17) 0.0018(16) -0.0031(16) O7 0.021(2) 0.020(2) 0.028(3) 0.0007(19) 0.0019(18) 0.0040(17) O8 0.0147(19) 0.026(2) 0.018(2) 0.0028(18) 0.0094(16) 0.0039(17) O9 0.014(2) 0.026(2) 0.019(2) -0.003(2) 0.0059(16) -0.0008(16) C1 0.008(2) 0.016(3) 0.013(3) 0.000(2) 0.002(2) 0.000(2) C2 0.013(2) 0.016(3) 0.012(3) -0.003(2) 0.002(2) -0.001(2) C3 0.019(3) 0.034(4) 0.012(3) -0.001(3) 0.011(2) 0.002(3) C4 0.016(3) 0.031(4) 0.018(3) -0.003(3) 0.006(2) -0.001(2) C5 0.015(3) 0.018(3) 0.013(3) 0.001(2) 0.004(2) -0.001(2) C6 0.017(3) 0.021(3) 0.012(3) 0.002(2) 0.002(2) 0.000(2) C7 0.012(2) 0.021(3) 0.002(3) 0.002(2) -0.0001(18) -0.002(2) C8 0.019(3) 0.017(3) 0.011(3) -0.004(2) 0.001(2) -0.001(2) C9 0.015(3) 0.020(3) 0.018(3) 0.002(2) 0.003(2) -0.001(2) C10 0.013(2) 0.015(3) 0.015(3) 0.002(2) 0.005(2) -0.001(2) C11 0.017(3) 0.015(3) 0.021(3) 0.003(2) 0.008(2) 0.004(2) C12 0.012(2) 0.020(3) 0.017(3) 0.000(3) 0.000(2) -0.004(2) C13 0.011(3) 0.029(3) 0.020(3) 0.000(3) 0.000(2) 0.002(2) C14 0.019(3) 0.024(3) 0.021(3) -0.006(3) 0.008(2) 0.001(2) C15 0.014(3) 0.010(3) 0.020(3) 0.000(2) 0.005(2) 0.001(2) C16 0.010(2) 0.012(3) 0.015(3) -0.003(2) 0.001(2) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O8 2.319(4) 1_655 ? Eu1 O1 2.366(4) . ? Eu1 O7 2.372(4) 3_565 ? Eu1 O2 2.378(4) 2_645 ? Eu1 O4 2.449(4) 4_565 ? Eu1 O6 2.532(4) 3 ? Eu1 O9 2.562(4) . ? Eu1 O3 2.589(4) 2_645 ? Eu1 O3 2.621(4) 4_565 ? Eu1 C8 2.900(6) 4_565 ? Eu1 Eu1 4.2081(14) 3_655 ? O1 C7 1.255(7) . ? O2 C7 1.252(6) . ? O2 Eu1 2.378(4) 2_655 ? O3 C8 1.289(6) . ? O3 Eu1 2.589(4) 2_655 ? O3 Eu1 2.621(4) 4_566 ? O4 C8 1.240(7) . ? O4 Eu1 2.449(4) 4_566 ? O5 C15 1.302(7) . ? O5 H1 0.85(5) . ? O6 C15 1.222(6) . ? O6 Eu1 2.532(4) 3 ? O7 C16 1.246(7) . ? O7 Eu1 2.372(4) 3_565 ? O8 C16 1.246(7) . ? O8 Eu1 2.319(4) 1_455 ? O9 H9B 0.85(6) . ? O9 H9A 0.84(7) . ? C1 C6 1.386(7) . ? C1 C2 1.397(8) . ? C1 C7 1.511(7) . ? C2 C3 1.394(7) . ? C2 C8 1.506(8) . ? C3 C4 1.389(8) . ? C3 H3 0.9300 . ? C4 C5 1.395(8) . ? C4 H4 0.9300 . ? C5 C6 1.391(7) . ? C5 C12 1.490(7) . ? C6 H6 0.9300 . ? C8 Eu1 2.900(6) 4_566 ? C9 C14 1.389(8) . ? C9 C10 1.399(8) . ? C9 C15 1.485(8) . ? C10 C11 1.402(8) . ? C10 C16 1.505(7) . ? C11 C12 1.403(7) . ? C11 H11 0.9300 . ? C12 C13 1.387(8) . ? C13 C14 1.385(8) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Eu1 O1 136.89(14) 1_655 . ? O8 Eu1 O7 90.00(14) 1_655 3_565 ? O1 Eu1 O7 76.29(15) . 3_565 ? O8 Eu1 O2 88.65(14) 1_655 2_645 ? O1 Eu1 O2 77.55(14) . 2_645 ? O7 Eu1 O2 139.77(14) 3_565 2_645 ? O8 Eu1 O4 126.76(14) 1_655 4_565 ? O1 Eu1 O4 86.65(14) . 4_565 ? O7 Eu1 O4 69.45(14) 3_565 4_565 ? O2 Eu1 O4 138.32(13) 2_645 4_565 ? O8 Eu1 O6 139.03(14) 1_655 3 ? O1 Eu1 O6 74.40(14) . 3 ? O7 Eu1 O6 128.38(13) 3_565 3 ? O2 Eu1 O6 71.33(13) 2_645 3 ? O4 Eu1 O6 67.31(13) 4_565 3 ? O8 Eu1 O9 66.67(14) 1_655 . ? O1 Eu1 O9 70.38(13) . . ? O7 Eu1 O9 66.69(14) 3_565 . ? O2 Eu1 O9 76.00(14) 2_645 . ? O4 Eu1 O9 134.01(14) 4_565 . ? O6 Eu1 O9 136.01(14) 3 . ? O8 Eu1 O3 68.86(13) 1_655 2_645 ? O1 Eu1 O3 137.37(14) . 2_645 ? O7 Eu1 O3 145.79(15) 3_565 2_645 ? O2 Eu1 O3 68.81(13) 2_645 2_645 ? O4 Eu1 O3 101.26(13) 4_565 2_645 ? O6 Eu1 O3 70.60(13) 3 2_645 ? O9 Eu1 O3 122.81(12) . 2_645 ? O8 Eu1 O3 76.78(13) 1_655 4_565 ? O1 Eu1 O3 136.11(13) . 4_565 ? O7 Eu1 O3 77.00(14) 3_565 4_565 ? O2 Eu1 O3 141.05(13) 2_645 4_565 ? O4 Eu1 O3 51.37(12) 4_565 4_565 ? O6 Eu1 O3 96.47(13) 3 4_565 ? O9 Eu1 O3 127.24(14) . 4_565 ? O3 Eu1 O3 72.24(14) 2_645 4_565 ? O8 Eu1 C8 102.26(16) 1_655 4_565 ? O1 Eu1 C8 110.63(15) . 4_565 ? O7 Eu1 C8 70.20(16) 3_565 4_565 ? O2 Eu1 C8 148.78(15) 2_645 4_565 ? O4 Eu1 C8 25.03(14) 4_565 4_565 ? O6 Eu1 C8 81.76(15) 3 4_565 ? O9 Eu1 C8 135.20(15) . 4_565 ? O3 Eu1 C8 87.78(15) 2_645 4_565 ? O3 Eu1 C8 26.38(14) 4_565 4_565 ? O8 Eu1 Eu1 68.64(10) 1_655 3_655 ? O1 Eu1 Eu1 154.35(10) . 3_655 ? O7 Eu1 Eu1 111.63(12) 3_565 3_655 ? O2 Eu1 Eu1 105.19(10) 2_645 3_655 ? O4 Eu1 Eu1 74.42(10) 4_565 3_655 ? O6 Eu1 Eu1 82.29(10) 3 3_655 ? O9 Eu1 Eu1 135.26(10) . 3_655 ? O3 Eu1 Eu1 36.38(9) 2_645 3_655 ? O3 Eu1 Eu1 35.86(9) 4_565 3_655 ? C8 Eu1 Eu1 54.42(12) 4_565 3_655 ? C7 O1 Eu1 150.7(4) . . ? C7 O2 Eu1 142.3(4) . 2_655 ? C8 O3 Eu1 122.2(4) . 2_655 ? C8 O3 Eu1 89.0(3) . 4_566 ? Eu1 O3 Eu1 107.76(14) 2_655 4_566 ? C8 O4 Eu1 98.3(3) . 4_566 ? C15 O5 H1 114(3) . . ? C15 O6 Eu1 133.3(4) . 3 ? C16 O7 Eu1 166.0(4) . 3_565 ? C16 O8 Eu1 142.3(4) . 1_455 ? Eu1 O9 H9B 110(3) . . ? Eu1 O9 H9A 92(4) . . ? H9B O9 H9A 111(4) . . ? C6 C1 C2 119.8(5) . . ? C6 C1 C7 113.5(5) . . ? C2 C1 C7 126.7(5) . . ? C3 C2 C1 117.5(5) . . ? C3 C2 C8 116.8(5) . . ? C1 C2 C8 125.6(5) . . ? C4 C3 C2 122.4(5) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C3 C4 C5 120.1(5) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 117.3(5) . . ? C6 C5 C12 120.0(5) . . ? C4 C5 C12 122.6(5) . . ? C1 C6 C5 122.9(5) . . ? C1 C6 H6 118.6 . . ? C5 C6 H6 118.6 . . ? O2 C7 O1 124.5(5) . . ? O2 C7 C1 120.5(5) . . ? O1 C7 C1 114.8(5) . . ? O4 C8 O3 121.1(5) . . ? O4 C8 C2 117.4(5) . . ? O3 C8 C2 121.3(5) . . ? O4 C8 Eu1 56.6(3) . 4_566 ? O3 C8 Eu1 64.6(3) . 4_566 ? C2 C8 Eu1 170.0(4) . 4_566 ? C14 C9 C10 119.7(5) . . ? C14 C9 C15 119.3(5) . . ? C10 C9 C15 120.5(5) . . ? C9 C10 C11 119.3(5) . . ? C9 C10 C16 123.5(5) . . ? C11 C10 C16 117.2(5) . . ? C10 C11 C12 121.0(5) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 118.1(5) . . ? C13 C12 C5 120.5(5) . . ? C11 C12 C5 121.4(5) . . ? C14 C13 C12 121.6(5) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C9 120.2(6) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? O6 C15 O5 123.4(5) . . ? O6 C15 C9 123.2(5) . . ? O5 C15 C9 113.4(5) . . ? O7 C16 O8 124.7(5) . . ? O7 C16 C10 119.0(5) . . ? O8 C16 C10 116.2(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 O8 Eu1 O1 C7 13.6(8) 1_655 . . . ? O7 Eu1 O1 C7 -61.3(7) 3_565 . . . ? O2 Eu1 O1 C7 87.9(7) 2_645 . . . ? O4 Eu1 O1 C7 -130.9(8) 4_565 . . . ? O6 Eu1 O1 C7 161.7(8) 3 . . . ? O9 Eu1 O1 C7 8.5(7) . . . . ? O3 Eu1 O1 C7 126.1(7) 2_645 . . . ? O3 Eu1 O1 C7 -115.3(7) 4_565 . . . ? C8 Eu1 O1 C7 -123.6(7) 4_565 . . . ? Eu1 Eu1 O1 C7 -172.9(6) 3_655 . . . ? C6 C1 C2 C3 -2.4(8) . . . . ? C7 C1 C2 C3 177.3(5) . . . . ? C6 C1 C2 C8 173.0(5) . . . . ? C7 C1 C2 C8 -7.4(9) . . . . ? C1 C2 C3 C4 1.0(9) . . . . ? C8 C2 C3 C4 -174.8(6) . . . . ? C2 C3 C4 C5 0.9(10) . . . . ? C3 C4 C5 C6 -1.3(9) . . . . ? C3 C4 C5 C12 175.5(6) . . . . ? C2 C1 C6 C5 2.0(9) . . . . ? C7 C1 C6 C5 -177.7(5) . . . . ? C4 C5 C6 C1 -0.1(9) . . . . ? C12 C5 C6 C1 -177.0(5) . . . . ? Eu1 O2 C7 O1 -119.6(6) 2_655 . . . ? Eu1 O2 C7 C1 65.4(7) 2_655 . . . ? Eu1 O1 C7 O2 -12.3(11) . . . . ? Eu1 O1 C7 C1 162.9(5) . . . . ? C6 C1 C7 O2 127.2(6) . . . . ? C2 C1 C7 O2 -52.5(8) . . . . ? C6 C1 C7 O1 -48.2(7) . . . . ? C2 C1 C7 O1 132.1(6) . . . . ? Eu1 O4 C8 O3 -4.7(6) 4_566 . . . ? Eu1 O4 C8 C2 170.7(4) 4_566 . . . ? Eu1 O3 C8 O4 -106.1(6) 2_655 . . . ? Eu1 O3 C8 O4 4.3(6) 4_566 . . . ? Eu1 O3 C8 C2 78.7(6) 2_655 . . . ? Eu1 O3 C8 C2 -170.9(5) 4_566 . . . ? Eu1 O3 C8 Eu1 -110.5(3) 2_655 . . 4_566 ? C3 C2 C8 O4 -2.2(8) . . . . ? C1 C2 C8 O4 -177.5(6) . . . . ? C3 C2 C8 O3 173.2(5) . . . . ? C1 C2 C8 O3 -2.1(9) . . . . ? C3 C2 C8 Eu1 49(2) . . . 4_566 ? C1 C2 C8 Eu1 -126(2) . . . 4_566 ? C14 C9 C10 C11 -3.7(9) . . . . ? C15 C9 C10 C11 168.6(5) . . . . ? C14 C9 C10 C16 178.2(5) . . . . ? C15 C9 C10 C16 -9.5(9) . . . . ? C9 C10 C11 C12 1.3(9) . . . . ? C16 C10 C11 C12 179.5(5) . . . . ? C10 C11 C12 C13 2.5(9) . . . . ? C10 C11 C12 C5 -174.5(5) . . . . ? C6 C5 C12 C13 21.3(9) . . . . ? C4 C5 C12 C13 -155.4(6) . . . . ? C6 C5 C12 C11 -161.8(6) . . . . ? C4 C5 C12 C11 21.5(9) . . . . ? C11 C12 C13 C14 -3.9(9) . . . . ? C5 C12 C13 C14 173.1(6) . . . . ? C12 C13 C14 C9 1.6(10) . . . . ? C10 C9 C14 C13 2.3(9) . . . . ? C15 C9 C14 C13 -170.1(6) . . . . ? Eu1 O6 C15 O5 83.5(7) 3 . . . ? Eu1 O6 C15 C9 -94.5(6) 3 . . . ? C14 C9 C15 O6 156.1(6) . . . . ? C10 C9 C15 O6 -16.2(9) . . . . ? C14 C9 C15 O5 -22.0(8) . . . . ? C10 C9 C15 O5 165.7(5) . . . . ? Eu1 O7 C16 O8 83.0(17) 3_565 . . . ? Eu1 O7 C16 C10 -94.7(17) 3_565 . . . ? Eu1 O8 C16 O7 19.8(10) 1_455 . . . ? Eu1 O8 C16 C10 -162.4(4) 1_455 . . . ? C9 C10 C16 O7 -69.1(8) . . . . ? C11 C10 C16 O7 112.8(6) . . . . ? C9 C10 C16 O8 112.9(7) . . . . ? C11 C10 C16 O8 -65.2(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H1 O9 0.86(9) 1.85(8) 2.696(6) 165(8) 4_465 O9 H9A O2 0.84(7) 1.95(7) 2.782(6) 169(8) . O9 H9B O3 0.85(6) 2.29(6) 3.134(6) 170(8) 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.227 _refine_diff_density_min -0.885 _refine_diff_density_rms 0.206 # Attachment 'Gd_complex.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 628277' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H9 Gd O9' _chemical_formula_sum 'C16 H9 Gd O9' _chemical_formula_weight 502.48 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' Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' 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 13.0362(10) _cell_length_b 6.7037(4) _cell_length_c 16.4150(12) _cell_angle_alpha 90.00 _cell_angle_beta 108.589(3) _cell_angle_gamma 90.00 _cell_volume 1359.68(17) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3721 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.9 _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 ? _exptl_crystal_density_diffrn 2.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 4.937 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5888 _exptl_absorpt_correction_T_max 0.6935 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10148 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0365 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 27.85 _reflns_number_total 3220 _reflns_number_gt 2803 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_cell_refinement 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_data_reduction 'CrystalClear (Rigaku/MSC Inc., 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.0255P)^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 3220 _refine_ls_number_parameters 248 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0480 _refine_ls_wR_factor_gt 0.0463 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 0.470641(9) 0.186416(17) 0.093514(8) 0.00947(5) Uani 1 1 d . . . O1 O 0.37564(16) 0.2894(3) 0.18657(14) 0.0161(4) Uani 1 1 d . . . O2 O 0.42197(14) 0.5550(3) 0.27182(12) 0.0140(4) Uani 1 1 d . . . O3 O 0.42347(14) 0.3760(3) 0.42749(13) 0.0165(4) Uani 1 1 d . . . O4 O 0.29407(15) 0.3746(3) 0.48712(13) 0.0172(4) Uani 1 1 d . . . O5 O -0.25825(16) 0.1213(3) -0.19535(14) 0.0224(5) Uani 1 1 d . . . O6 O -0.38036(14) 0.1242(3) -0.12523(13) 0.0172(4) Uani 1 1 d . . . O7 O -0.39017(16) 0.5086(3) -0.03287(15) 0.0227(5) Uani 1 1 d . . . O8 O -0.37196(16) 0.2760(3) 0.06663(14) 0.0189(4) Uani 1 1 d . . . O9 O 0.56242(17) 0.4926(3) 0.17839(15) 0.0183(4) Uani 1 1 d . . . C1 C 0.25227(19) 0.3914(4) 0.25583(17) 0.0111(5) Uani 1 1 d . . . C2 C 0.2348(2) 0.3889(4) 0.33522(17) 0.0119(5) Uani 1 1 d . . . C3 C 0.1278(2) 0.3758(4) 0.33565(19) 0.0176(6) Uani 1 1 d . . . H3 H 0.1145 0.3760 0.3881 0.021 Uiso 1 1 calc R . . C4 C 0.0412(2) 0.3626(5) 0.2606(2) 0.0189(6) Uani 1 1 d . . . H4 H -0.0289 0.3554 0.2633 0.023 Uiso 1 1 calc R . . C5 C 0.0579(2) 0.3600(4) 0.18105(18) 0.0139(5) Uani 1 1 d . . . C6 C 0.1650(2) 0.3744(4) 0.18026(18) 0.0146(5) Uani 1 1 d . . . H6 H 0.1782 0.3725 0.1278 0.017 Uiso 1 1 calc R . . C7 C 0.35956(19) 0.4115(4) 0.23902(17) 0.0110(5) Uani 1 1 d . . . C8 C 0.3221(2) 0.3830(4) 0.42154(18) 0.0130(5) Uani 1 1 d . . . C9 C -0.2014(2) 0.2413(4) -0.05319(18) 0.0134(5) Uani 1 1 d . . . C10 C -0.2246(2) 0.3278(4) 0.01664(18) 0.0120(5) Uani 1 1 d . . . C11 C -0.1402(2) 0.3702(4) 0.09179(18) 0.0153(5) Uani 1 1 d . . . H11 H -0.1560 0.4253 0.1384 0.018 Uiso 1 1 calc R . . C12 C -0.0322(2) 0.3315(4) 0.09837(18) 0.0151(6) Uani 1 1 d . . . C13 C -0.0104(2) 0.2553(5) 0.0263(2) 0.0196(6) Uani 1 1 d . . . H13 H 0.0609 0.2342 0.0284 0.024 Uiso 1 1 calc R . . C14 C -0.0938(2) 0.2108(4) -0.0482(2) 0.0180(6) Uani 1 1 d . . . H14 H -0.0779 0.1600 -0.0955 0.022 Uiso 1 1 calc R . . C15 C -0.2889(2) 0.1589(4) -0.12807(18) 0.0135(5) Uani 1 1 d . . . C16 C -0.3388(2) 0.3750(4) 0.01536(17) 0.0119(5) Uani 1 1 d . . . H9B H 0.558(3) 0.592(7) 0.144(3) 0.048(13) Uiso 1 1 d . . . H9A H 0.527(3) 0.527(6) 0.209(3) 0.051(14) Uiso 1 1 d . . . H1 H -0.319(4) 0.069(7) -0.243(4) 0.077(16) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Gd1 0.00774(8) 0.01302(8) 0.00757(8) 0.00016(5) 0.00232(5) 0.00089(5) O1 0.0157(10) 0.0180(10) 0.0179(11) -0.0048(7) 0.0100(8) -0.0016(7) O2 0.0103(8) 0.0183(9) 0.0122(10) -0.0032(8) 0.0020(7) -0.0038(7) O3 0.0092(9) 0.0226(10) 0.0154(11) 0.0020(8) 0.0007(8) 0.0007(8) O4 0.0141(9) 0.0261(10) 0.0106(10) 0.0008(8) 0.0027(8) 0.0027(8) O5 0.0155(10) 0.0369(12) 0.0141(11) -0.0070(9) 0.0037(8) -0.0028(9) O6 0.0118(9) 0.0196(10) 0.0185(11) -0.0006(8) 0.0024(8) -0.0027(8) O7 0.0185(10) 0.0179(10) 0.0263(13) 0.0047(8) -0.0004(9) 0.0053(8) O8 0.0136(10) 0.0246(11) 0.0213(12) 0.0026(8) 0.0096(9) 0.0018(8) O9 0.0162(10) 0.0233(11) 0.0159(11) -0.0029(8) 0.0058(9) 0.0005(8) C1 0.0079(11) 0.0124(12) 0.0120(13) -0.0001(9) 0.0019(10) 0.0012(9) C2 0.0092(12) 0.0148(12) 0.0112(13) -0.0010(10) 0.0023(10) -0.0005(10) C3 0.0121(13) 0.0285(15) 0.0118(14) 0.0006(11) 0.0033(11) -0.0001(11) C4 0.0081(12) 0.0314(15) 0.0175(16) -0.0028(12) 0.0045(11) 0.0006(11) C5 0.0080(12) 0.0189(13) 0.0131(14) -0.0008(10) 0.0011(11) -0.0003(10) C6 0.0120(13) 0.0202(13) 0.0115(14) -0.0002(10) 0.0037(11) -0.0020(10) C7 0.0078(11) 0.0152(13) 0.0092(13) 0.0035(10) 0.0013(10) 0.0025(10) C8 0.0129(12) 0.0112(12) 0.0140(14) -0.0023(10) 0.0032(11) 0.0001(10) C9 0.0118(13) 0.0167(13) 0.0104(13) 0.0020(10) 0.0016(11) -0.0020(10) C10 0.0107(13) 0.0133(12) 0.0122(14) 0.0022(9) 0.0037(11) -0.0017(10) C11 0.0123(13) 0.0200(13) 0.0129(14) -0.0015(10) 0.0029(11) -0.0018(11) C12 0.0103(13) 0.0198(14) 0.0137(15) 0.0009(10) 0.0018(11) -0.0008(10) C13 0.0072(13) 0.0300(15) 0.0206(16) -0.0029(12) 0.0029(11) -0.0020(12) C14 0.0139(14) 0.0284(16) 0.0126(14) -0.0041(11) 0.0057(11) -0.0002(11) C15 0.0133(13) 0.0128(13) 0.0133(14) 0.0010(10) 0.0025(11) 0.0011(10) C16 0.0087(12) 0.0148(12) 0.0108(13) -0.0026(10) 0.0011(10) -0.0004(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 Gd1 O8 2.311(2) 1_655 ? Gd1 O1 2.356(2) . ? Gd1 O7 2.3676(18) 3_565 ? Gd1 O2 2.3768(18) 2_645 ? Gd1 O4 2.4399(19) 4_565 ? Gd1 O6 2.526(2) 3 ? Gd1 O9 2.554(2) . ? Gd1 O3 2.5805(19) 2_645 ? Gd1 O3 2.629(2) 4_565 ? Gd1 C8 2.907(3) 4_565 ? O1 C7 1.253(3) . ? O2 C7 1.264(3) . ? O2 Gd1 2.3767(18) 2_655 ? O3 C8 1.294(3) . ? O3 Gd1 2.5805(19) 2_655 ? O3 Gd1 2.629(2) 4_566 ? O4 C8 1.244(3) . ? O4 Gd1 2.4398(19) 4_566 ? O5 C15 1.313(4) . ? O5 H1 0.98(5) . ? O6 C15 1.230(3) . ? O6 Gd1 2.527(2) 3 ? O7 C16 1.240(3) . ? O7 Gd1 2.3676(18) 3_565 ? O8 C16 1.252(3) . ? O8 Gd1 2.312(2) 1_455 ? O9 H9B 0.86(5) . ? O9 H9A 0.81(5) . ? C1 C2 1.393(4) . ? C1 C6 1.395(4) . ? C1 C7 1.515(3) . ? C2 C3 1.400(4) . ? C2 C8 1.509(4) . ? C3 C4 1.384(4) . ? C3 H3 0.9300 . ? C4 C5 1.390(4) . ? C4 H4 0.9300 . ? C5 C6 1.403(4) . ? C5 C12 1.497(4) . ? C6 H6 0.9300 . ? C8 Gd1 2.907(3) 4_566 ? C9 C14 1.393(4) . ? C9 C10 1.401(4) . ? C9 C15 1.491(4) . ? C10 C11 1.396(4) . ? C10 C16 1.516(4) . ? C11 C12 1.402(4) . ? C11 H11 0.9300 . ? C12 C13 1.399(4) . ? C13 C14 1.385(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Gd1 O1 136.87(7) 1_655 . ? O8 Gd1 O7 89.81(7) 1_655 3_565 ? O1 Gd1 O7 76.43(8) . 3_565 ? O8 Gd1 O2 88.76(7) 1_655 2_645 ? O1 Gd1 O2 77.36(7) . 2_645 ? O7 Gd1 O2 139.62(7) 3_565 2_645 ? O8 Gd1 O4 126.81(7) 1_655 4_565 ? O1 Gd1 O4 86.69(7) . 4_565 ? O7 Gd1 O4 69.71(7) 3_565 4_565 ? O2 Gd1 O4 138.17(6) 2_645 4_565 ? O8 Gd1 O6 138.91(7) 1_655 3 ? O1 Gd1 O6 74.47(7) . 3 ? O7 Gd1 O6 128.70(6) 3_565 3 ? O2 Gd1 O6 71.21(6) 2_645 3 ? O4 Gd1 O6 67.31(6) 4_565 3 ? O8 Gd1 O9 66.76(7) 1_655 . ? O1 Gd1 O9 70.27(7) . . ? O7 Gd1 O9 66.62(7) 3_565 . ? O2 Gd1 O9 75.87(7) 2_645 . ? O4 Gd1 O9 134.12(7) 4_565 . ? O6 Gd1 O9 135.89(7) 3 . ? O8 Gd1 O3 68.83(7) 1_655 2_645 ? O1 Gd1 O3 137.49(7) . 2_645 ? O7 Gd1 O3 145.54(8) 3_565 2_645 ? O2 Gd1 O3 69.13(6) 2_645 2_645 ? O4 Gd1 O3 101.07(6) 4_565 2_645 ? O6 Gd1 O3 70.55(7) 3 2_645 ? O9 Gd1 O3 122.92(6) . 2_645 ? O8 Gd1 O3 76.82(7) 1_655 4_565 ? O1 Gd1 O3 136.15(6) . 4_565 ? O7 Gd1 O3 77.03(7) 3_565 4_565 ? O2 Gd1 O3 141.16(6) 2_645 4_565 ? O4 Gd1 O3 51.38(6) 4_565 4_565 ? O6 Gd1 O3 96.44(6) 3 4_565 ? O9 Gd1 O3 127.40(7) . 4_565 ? O3 Gd1 O3 72.04(7) 2_645 4_565 ? O8 Gd1 C8 102.30(8) 1_655 4_565 ? O1 Gd1 C8 110.59(7) . 4_565 ? O7 Gd1 C8 70.20(7) 3_565 4_565 ? O2 Gd1 C8 148.91(7) 2_645 4_565 ? O4 Gd1 C8 25.01(7) 4_565 4_565 ? O6 Gd1 C8 81.86(7) 3 4_565 ? O9 Gd1 C8 135.21(7) . 4_565 ? O3 Gd1 C8 87.71(7) 2_645 4_565 ? O3 Gd1 C8 26.43(7) 4_565 4_565 ? C7 O1 Gd1 151.00(18) . . ? C7 O2 Gd1 141.86(17) . 2_655 ? C8 O3 Gd1 122.48(16) . 2_655 ? C8 O3 Gd1 88.85(16) . 4_566 ? Gd1 O3 Gd1 107.97(7) 2_655 4_566 ? C8 O4 Gd1 99.00(16) . 4_566 ? C15 O5 H1 111(3) . . ? C15 O6 Gd1 133.19(17) . 3 ? C16 O7 Gd1 165.5(2) . 3_565 ? C16 O8 Gd1 141.59(18) . 1_455 ? Gd1 O9 H9B 110(3) . . ? Gd1 O9 H9A 108(3) . . ? H9B O9 H9A 104(4) . . ? C2 C1 C6 120.0(2) . . ? C2 C1 C7 127.4(2) . . ? C6 C1 C7 112.6(2) . . ? C1 C2 C3 117.8(2) . . ? C1 C2 C8 125.4(2) . . ? C3 C2 C8 116.6(2) . . ? C4 C3 C2 122.1(3) . . ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 . . ? C3 C4 C5 120.6(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 117.5(2) . . ? C4 C5 C12 122.7(2) . . ? C6 C5 C12 119.7(3) . . ? C1 C6 C5 121.9(3) . . ? C1 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? O1 C7 O2 124.3(2) . . ? O1 C7 C1 115.7(2) . . ? O2 C7 C1 119.8(2) . . ? O4 C8 O3 120.5(2) . . ? O4 C8 C2 118.1(2) . . ? O3 C8 C2 121.2(2) . . ? O4 C8 Gd1 56.00(14) . 4_566 ? O3 C8 Gd1 64.73(14) . 4_566 ? C2 C8 Gd1 170.29(18) . 4_566 ? C14 C9 C10 119.2(3) . . ? C14 C9 C15 119.1(3) . . ? C10 C9 C15 121.3(2) . . ? C11 C10 C9 119.5(2) . . ? C11 C10 C16 117.6(2) . . ? C9 C10 C16 122.9(2) . . ? C10 C11 C12 121.3(3) . . ? C10 C11 H11 119.3 . . ? C12 C11 H11 119.3 . . ? C13 C12 C11 118.2(2) . . ? C13 C12 C5 120.1(2) . . ? C11 C12 C5 121.6(3) . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C9 120.8(3) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? O6 C15 O5 123.7(3) . . ? O6 C15 C9 122.4(3) . . ? O5 C15 C9 113.9(2) . . ? O7 C16 O8 125.5(3) . . ? O7 C16 C10 119.2(2) . . ? O8 C16 C10 115.3(2) . . ? 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 O8 Gd1 O1 C7 12.4(4) 1_655 . . . ? O7 Gd1 O1 C7 -62.3(4) 3_565 . . . ? O2 Gd1 O1 C7 86.7(4) 2_645 . . . ? O4 Gd1 O1 C7 -132.3(4) 4_565 . . . ? O6 Gd1 O1 C7 160.4(4) 3 . . . ? O9 Gd1 O1 C7 7.3(4) . . . . ? O3 Gd1 O1 C7 124.9(4) 2_645 . . . ? O3 Gd1 O1 C7 -116.6(4) 4_565 . . . ? C8 Gd1 O1 C7 -124.8(4) 4_565 . . . ? C6 C1 C2 C3 -2.1(4) . . . . ? C7 C1 C2 C3 177.8(2) . . . . ? C6 C1 C2 C8 172.8(2) . . . . ? C7 C1 C2 C8 -7.3(4) . . . . ? C1 C2 C3 C4 0.9(4) . . . . ? C8 C2 C3 C4 -174.4(3) . . . . ? C2 C3 C4 C5 0.6(5) . . . . ? C3 C4 C5 C6 -1.0(4) . . . . ? C3 C4 C5 C12 175.6(3) . . . . ? C2 C1 C6 C5 1.8(4) . . . . ? C7 C1 C6 C5 -178.1(2) . . . . ? C4 C5 C6 C1 -0.2(4) . . . . ? C12 C5 C6 C1 -176.9(2) . . . . ? Gd1 O1 C7 O2 -10.4(5) . . . . ? Gd1 O1 C7 C1 163.8(3) . . . . ? Gd1 O2 C7 O1 -120.6(3) 2_655 . . . ? Gd1 O2 C7 C1 65.5(3) 2_655 . . . ? C2 C1 C7 O1 132.7(3) . . . . ? C6 C1 C7 O1 -47.5(3) . . . . ? C2 C1 C7 O2 -52.9(4) . . . . ? C6 C1 C7 O2 127.0(3) . . . . ? Gd1 O4 C8 O3 -5.4(3) 4_566 . . . ? Gd1 O4 C8 C2 170.95(19) 4_566 . . . ? Gd1 O3 C8 O4 -105.7(3) 2_655 . . . ? Gd1 O3 C8 O4 4.9(3) 4_566 . . . ? Gd1 O3 C8 C2 78.1(3) 2_655 . . . ? Gd1 O3 C8 C2 -171.3(2) 4_566 . . . ? Gd1 O3 C8 Gd1 -110.67(16) 2_655 . . 4_566 ? C1 C2 C8 O4 -177.6(3) . . . . ? C3 C2 C8 O4 -2.6(4) . . . . ? C1 C2 C8 O3 -1.3(4) . . . . ? C3 C2 C8 O3 173.7(3) . . . . ? C14 C9 C10 C11 -4.0(4) . . . . ? C15 C9 C10 C11 168.5(2) . . . . ? C14 C9 C10 C16 177.1(3) . . . . ? C15 C9 C10 C16 -10.4(4) . . . . ? C9 C10 C11 C12 1.2(4) . . . . ? C16 C10 C11 C12 -179.9(2) . . . . ? C10 C11 C12 C13 2.2(4) . . . . ? C10 C11 C12 C5 -174.6(3) . . . . ? C4 C5 C12 C13 -155.6(3) . . . . ? C6 C5 C12 C13 21.0(4) . . . . ? C4 C5 C12 C11 21.2(4) . . . . ? C6 C5 C12 C11 -162.3(3) . . . . ? C11 C12 C13 C14 -2.9(4) . . . . ? C5 C12 C13 C14 174.0(3) . . . . ? C12 C13 C14 C9 0.1(5) . . . . ? C10 C9 C14 C13 3.4(4) . . . . ? C15 C9 C14 C13 -169.3(3) . . . . ? Gd1 O6 C15 O5 82.7(3) 3 . . . ? Gd1 O6 C15 C9 -95.0(3) 3 . . . ? C14 C9 C15 O6 157.0(3) . . . . ? C10 C9 C15 O6 -15.5(4) . . . . ? C14 C9 C15 O5 -20.9(4) . . . . ? C10 C9 C15 O5 166.6(2) . . . . ? Gd1 O7 C16 O8 83.5(8) 3_565 . . . ? Gd1 O7 C16 C10 -94.2(8) 3_565 . . . ? Gd1 O8 C16 O7 19.7(5) 1_455 . . . ? Gd1 O8 C16 C10 -162.5(2) 1_455 . . . ? C11 C10 C16 O7 113.1(3) . . . . ? C9 C10 C16 O7 -68.0(4) . . . . ? C11 C10 C16 O8 -64.8(3) . . . . ? C9 C10 C16 O8 114.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O9 H9B O3 0.86(5) 2.29(5) 3.140(3) 169(4) 2_655 O9 H9A O2 0.81(5) 1.97(5) 2.770(3) 167(4) . O5 H1 O9 0.98(5) 1.72(5) 2.693(3) 171(4) 4_465 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.532 _refine_diff_density_min -1.052 _refine_diff_density_rms 0.130