# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_706f _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 Dy N O11' _chemical_formula_weight 590.87 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' N N 0.0061 0.0033 '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 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 13.690(3) _cell_length_b 7.4779(15) _cell_length_c 21.285(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.04(2) _cell_angle_gamma 90.00 _cell_volume 1957.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4655 _cell_measurement_theta_min 2.04 _cell_measurement_theta_max 27.87 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.005 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1164 _exptl_absorpt_coefficient_mu 3.881 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3058 _exptl_absorpt_correction_T_max 0.5107 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18967 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_unetI/netI 0.0396 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.87 _reflns_number_total 4655 _reflns_number_gt 3932 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0274P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4655 _refine_ls_number_parameters 282 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0251 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0571 _refine_ls_wR_factor_gt 0.0561 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 Dy2 Dy 0.140915(9) 0.263274(15) -0.112053(6) 0.00752(5) Uani 1 1 d . . . O2 O 0.11772(14) 0.4606(2) -0.02800(9) 0.0109(4) Uani 1 1 d . . . O5 O 0.89768(15) 0.7204(2) 0.29580(10) 0.0149(4) Uani 1 1 d . . . O3 O 0.04315(16) 0.7177(3) 0.15954(11) 0.0181(4) Uani 1 1 d . . . O6 O 0.77117(16) 0.7188(2) 0.18410(10) 0.0141(4) Uani 1 1 d . . . O4 O 0.17714(16) 0.7434(2) 0.26719(10) 0.0166(5) Uani 1 1 d . . . C15 C 0.8014(2) 0.6995(3) 0.24942(14) 0.0108(5) Uani 1 1 d . . . O7 O 0.10268(15) 0.0958(2) -0.02959(9) 0.0161(4) Uani 1 1 d . . . H7A H 0.1212 0.1370 0.0113 0.019 Uiso 1 1 d R . . H7B H 0.0708 -0.0048 -0.0411 0.019 Uiso 1 1 d R . . C8 C 0.1416(2) 0.7090(3) 0.20280(14) 0.0096(5) Uani 1 1 d . . . O1 O 0.28551(15) 0.4060(2) -0.01060(9) 0.0149(4) Uani 1 1 d . . . O8 O 0.07488(15) -0.0044(2) -0.17711(10) 0.0163(4) Uani 1 1 d . . . H8A H 0.0692 -0.0988 -0.1567 0.020 Uiso 1 1 d R . . H8B H 0.0861 -0.0410 -0.2112 0.020 Uiso 1 1 d R . . C1 C 0.4087(2) 0.5927(3) 0.19824(13) 0.0094(5) Uani 1 1 d . . . C7 C 0.2192(2) 0.4644(3) 0.01107(13) 0.0107(5) Uani 1 1 d . . . C9 C 0.5263(2) 0.5960(3) 0.24735(13) 0.0095(5) Uani 1 1 d . . . N1 N 0.39120(19) -0.1858(3) -0.04695(12) 0.0171(5) Uani 1 1 d . . . O10 O 0.28783(15) 0.0609(2) -0.06090(10) 0.0174(4) Uani 1 1 d . . . C3 C 0.2596(2) 0.5335(3) 0.08425(13) 0.0099(5) Uani 1 1 d . . . C4 C 0.1854(2) 0.5920(3) 0.10796(13) 0.0095(5) Uani 1 1 d . . . H4 H 0.1115 0.5919 0.0779 0.011 Uiso 1 1 calc R . . C2 C 0.3702(2) 0.5323(3) 0.12974(13) 0.0102(5) Uani 1 1 d . . . H2 H 0.4194 0.4903 0.1139 0.012 Uiso 1 1 calc R . . O9 O 0.09539(16) 0.5482(2) -0.16669(10) 0.0185(4) Uani 1 1 d . . . H9B H 0.0647 0.5555 -0.2110 0.022 Uiso 1 1 d R . . H9A H 0.0582 0.6150 -0.1531 0.022 Uiso 1 1 d R . . C5 C 0.2214(2) 0.6505(3) 0.17635(13) 0.0094(5) Uani 1 1 d . . . C11 C 0.7154(2) 0.6459(3) 0.27252(13) 0.0094(5) Uani 1 1 d . . . C13 C 0.6687(2) 0.5589(4) 0.36525(14) 0.0140(6) Uani 1 1 d . . . H13 H 0.6898 0.5319 0.4121 0.017 Uiso 1 1 calc R . . C14 C 0.5598(2) 0.5551(3) 0.31771(14) 0.0118(5) Uani 1 1 d . . . H14 H 0.5080 0.5247 0.3331 0.014 Uiso 1 1 calc R . . C10 C 0.6057(2) 0.6413(3) 0.22559(13) 0.0097(5) Uani 1 1 d . . . H10 H 0.5848 0.6689 0.1788 0.012 Uiso 1 1 calc R . . C16 C 0.3176(2) -0.0672(4) -0.08539(15) 0.0184(6) Uani 1 1 d . . . H16 H 0.2861 -0.0805 -0.1337 0.022 Uiso 1 1 calc R . . C12 C 0.7455(2) 0.6032(3) 0.34235(14) 0.0135(6) Uani 1 1 d . . . H12 H 0.8187 0.6046 0.3740 0.016 Uiso 1 1 calc R . . C17 C 0.4439(2) -0.1714(4) 0.02880(14) 0.0231(7) Uani 1 1 d . . . H17A H 0.4386 -0.0505 0.0422 0.035 Uiso 1 1 calc R . . H17B H 0.5191 -0.2038 0.0461 0.035 Uiso 1 1 calc R . . H17C H 0.4090 -0.2502 0.0482 0.035 Uiso 1 1 calc R . . C6 C 0.3324(2) 0.6512(3) 0.22091(13) 0.0101(5) Uani 1 1 d . . . H6 H 0.3563 0.6914 0.2666 0.012 Uiso 1 1 calc R . . C18 C 0.4183(3) -0.3385(4) -0.07808(17) 0.0274(7) Uani 1 1 d . . . H18A H 0.3786 -0.3321 -0.1281 0.041 Uiso 1 1 calc R . . H18B H 0.3994 -0.4466 -0.0617 0.041 Uiso 1 1 calc R . . H18C H 0.4949 -0.3382 -0.0651 0.041 Uiso 1 1 calc R . . O11 O 1.00311(16) 0.7264(2) 0.44438(11) 0.0141(4) Uani 1 1 d . . . H11B H 0.9574 0.7649 0.4048 0.021 Uiso 1 1 d R . . H11A H 1.0270 0.8363 0.4495 0.021 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Dy2 0.00617(7) 0.00914(8) 0.00763(8) -0.00040(4) 0.00338(5) 0.00034(4) O2 0.0087(9) 0.0123(10) 0.0097(9) -0.0022(7) 0.0022(7) 0.0008(7) O5 0.0070(9) 0.0217(11) 0.0158(10) -0.0007(8) 0.0050(8) -0.0024(7) O3 0.0073(9) 0.0294(12) 0.0156(11) -0.0052(9) 0.0031(8) 0.0026(8) O6 0.0120(10) 0.0202(10) 0.0127(10) 0.0011(8) 0.0079(8) 0.0004(8) O4 0.0122(10) 0.0269(13) 0.0120(11) -0.0030(8) 0.0065(8) 0.0026(7) C15 0.0120(13) 0.0092(13) 0.0136(14) -0.0001(11) 0.0080(11) 0.0014(10) O7 0.0231(11) 0.0147(10) 0.0131(10) -0.0016(8) 0.0103(9) -0.0037(8) C8 0.0081(12) 0.0090(12) 0.0120(13) 0.0006(10) 0.0046(10) -0.0009(10) O1 0.0128(10) 0.0196(11) 0.0129(10) -0.0061(8) 0.0062(8) -0.0002(8) O8 0.0176(10) 0.0152(10) 0.0196(11) -0.0083(8) 0.0113(9) -0.0044(8) C1 0.0071(12) 0.0096(13) 0.0114(14) 0.0025(10) 0.0040(11) -0.0003(9) C7 0.0129(13) 0.0059(13) 0.0132(14) -0.0004(10) 0.0056(11) 0.0001(10) C9 0.0091(13) 0.0073(13) 0.0125(14) -0.0023(10) 0.0050(11) 0.0004(9) N1 0.0167(12) 0.0180(13) 0.0175(13) 0.0019(10) 0.0084(10) 0.0054(10) O10 0.0179(11) 0.0161(11) 0.0185(11) -0.0003(8) 0.0083(9) 0.0069(8) C3 0.0129(13) 0.0082(13) 0.0085(13) -0.0004(10) 0.0047(10) -0.0011(10) C4 0.0050(12) 0.0097(13) 0.0112(14) 0.0009(10) 0.0012(10) -0.0011(9) C2 0.0104(13) 0.0092(13) 0.0142(14) -0.0012(10) 0.0082(11) -0.0006(10) O9 0.0244(11) 0.0170(11) 0.0200(11) 0.0095(8) 0.0151(9) 0.0091(8) C5 0.0086(12) 0.0086(13) 0.0117(14) 0.0017(10) 0.0053(10) 0.0008(10) C11 0.0103(13) 0.0068(13) 0.0131(14) -0.0003(10) 0.0071(11) 0.0005(10) C13 0.0140(14) 0.0186(15) 0.0087(14) 0.0023(11) 0.0044(11) -0.0015(11) C14 0.0099(13) 0.0134(14) 0.0138(14) 0.0000(10) 0.0067(11) -0.0014(10) C10 0.0118(13) 0.0097(13) 0.0082(13) -0.0005(10) 0.0050(10) 0.0010(10) C16 0.0183(15) 0.0203(16) 0.0163(15) -0.0008(12) 0.0071(12) 0.0022(12) C12 0.0081(13) 0.0159(14) 0.0130(14) -0.0003(11) 0.0014(11) -0.0004(10) C17 0.0207(16) 0.0266(17) 0.0194(17) 0.0058(13) 0.0066(13) 0.0015(13) C6 0.0099(13) 0.0120(13) 0.0085(13) -0.0020(10) 0.0041(10) -0.0014(10) C18 0.0326(18) 0.0234(17) 0.0319(19) 0.0013(14) 0.0192(15) 0.0109(14) O11 0.0148(10) 0.0110(10) 0.0154(11) 0.0009(7) 0.0055(8) -0.0017(7) _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 Dy2 O3 2.271(2) 3_565 ? Dy2 O6 2.3322(19) 3_665 ? Dy2 O10 2.3662(19) . ? Dy2 O8 2.3755(18) . ? Dy2 O9 2.3757(18) . ? Dy2 O7 2.3935(18) . ? Dy2 O1 2.4428(19) . ? Dy2 O2 2.4450(18) . ? O2 C7 1.268(3) . ? O5 C15 1.262(3) . ? O3 C8 1.257(3) . ? O3 Dy2 2.270(2) 3_565 ? O6 C15 1.273(3) . ? O6 Dy2 2.3322(19) 3_665 ? O4 C8 1.263(3) . ? C15 C11 1.515(3) . ? O7 H7A 0.8499 . ? O7 H7B 0.8499 . ? C8 C5 1.497(3) . ? O1 C7 1.263(3) . ? O8 H8A 0.8500 . ? O8 H8B 0.8499 . ? C1 C2 1.390(3) . ? C1 C6 1.399(3) . ? C1 C9 1.486(3) . ? C7 C3 1.497(3) . ? C9 C14 1.394(3) . ? C9 C10 1.398(3) . ? N1 C16 1.322(3) . ? N1 C18 1.448(4) . ? N1 C17 1.453(4) . ? O10 C16 1.241(3) . ? C3 C4 1.388(3) . ? C3 C2 1.394(3) . ? C4 C5 1.387(3) . ? C4 H4 0.9300 . ? C2 H2 0.9300 . ? O9 H9B 0.8500 . ? O9 H9A 0.8499 . ? C5 C6 1.394(3) . ? C11 C10 1.392(3) . ? C11 C12 1.394(4) . ? C13 C12 1.380(3) . ? C13 C14 1.387(4) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C10 H10 0.9300 . ? C16 H16 0.9300 . ? C12 H12 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C6 H6 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O11 H11B 0.8497 . ? O11 H11A 0.8730 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Dy2 O6 119.73(7) 3_565 3_665 ? O3 Dy2 O10 142.94(7) 3_565 . ? O6 Dy2 O10 76.09(7) 3_665 . ? O3 Dy2 O8 74.30(7) 3_565 . ? O6 Dy2 O8 80.76(6) 3_665 . ? O10 Dy2 O8 76.01(7) . . ? O3 Dy2 O9 74.01(7) 3_565 . ? O6 Dy2 O9 74.14(6) 3_665 . ? O10 Dy2 O9 141.84(6) . . ? O8 Dy2 O9 121.30(8) . . ? O3 Dy2 O7 78.58(7) 3_565 . ? O6 Dy2 O7 148.70(6) 3_665 . ? O10 Dy2 O7 75.12(6) . . ? O8 Dy2 O7 80.61(7) . . ? O9 Dy2 O7 137.16(6) . . ? O3 Dy2 O1 132.56(7) 3_565 . ? O6 Dy2 O1 95.99(7) 3_665 . ? O10 Dy2 O1 71.18(7) . . ? O8 Dy2 O1 146.80(6) . . ? O9 Dy2 O1 88.72(7) . . ? O7 Dy2 O1 86.19(7) . . ? O3 Dy2 O2 79.20(7) 3_565 . ? O6 Dy2 O2 135.78(6) 3_665 . ? O10 Dy2 O2 113.99(6) . . ? O8 Dy2 O2 142.82(6) . . ? O9 Dy2 O2 74.12(6) . . ? O7 Dy2 O2 68.82(7) . . ? O1 Dy2 O2 53.46(6) . . ? C7 O2 Dy2 92.10(15) . . ? C8 O3 Dy2 162.40(18) . 3_565 ? C15 O6 Dy2 135.28(17) . 3_665 ? O5 C15 O6 124.6(2) . . ? O5 C15 C11 118.2(2) . . ? O6 C15 C11 117.3(2) . . ? Dy2 O7 H7A 119.9 . . ? Dy2 O7 H7B 120.1 . . ? H7A O7 H7B 120.0 . . ? O3 C8 O4 124.2(2) . . ? O3 C8 C5 117.7(2) . . ? O4 C8 C5 118.1(2) . . ? C7 O1 Dy2 92.33(15) . . ? Dy2 O8 H8A 119.9 . . ? Dy2 O8 H8B 127.1 . . ? H8A O8 H8B 105.1 . . ? C2 C1 C6 117.8(2) . . ? C2 C1 C9 122.5(2) . . ? C6 C1 C9 119.6(2) . . ? O1 C7 O2 120.6(2) . . ? O1 C7 C3 120.2(2) . . ? O2 C7 C3 119.2(2) . . ? C14 C9 C10 118.2(2) . . ? C14 C9 C1 119.7(2) . . ? C10 C9 C1 122.1(2) . . ? C16 N1 C18 121.7(3) . . ? C16 N1 C17 120.6(2) . . ? C18 N1 C17 117.7(2) . . ? C16 O10 Dy2 132.03(19) . . ? C4 C3 C2 119.6(2) . . ? C4 C3 C7 119.5(2) . . ? C2 C3 C7 120.9(2) . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C1 C2 C3 121.5(2) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? Dy2 O9 H9B 119.8 . . ? Dy2 O9 H9A 115.4 . . ? H9B O9 H9A 105.1 . . ? C4 C5 C6 119.6(2) . . ? C4 C5 C8 120.4(2) . . ? C6 C5 C8 120.0(2) . . ? C10 C11 C12 118.7(2) . . ? C10 C11 C15 121.4(2) . . ? C12 C11 C15 119.9(2) . . ? C12 C13 C14 119.3(2) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C13 C14 C9 121.3(2) . . ? C13 C14 H14 119.3 . . ? C9 C14 H14 119.3 . . ? C11 C10 C9 121.3(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? O10 C16 N1 124.0(3) . . ? O10 C16 H16 118.0 . . ? N1 C16 H16 118.0 . . ? C13 C12 C11 121.1(2) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C5 C6 C1 121.3(2) . . ? C5 C6 H6 119.3 . . ? C1 C6 H6 119.3 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? H11B O11 H11A 82.9 . . ? 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 O3 Dy2 O2 C7 176.34(15) 3_565 . . . ? O6 Dy2 O2 C7 -61.79(17) 3_665 . . . ? O10 Dy2 O2 C7 32.80(16) . . . . ? O8 Dy2 O2 C7 131.36(15) . . . . ? O9 Dy2 O2 C7 -107.39(15) . . . . ? O7 Dy2 O2 C7 94.52(15) . . . . ? O1 Dy2 O2 C7 -6.92(14) . . . . ? Dy2 O6 C15 O5 15.1(4) 3_665 . . . ? Dy2 O6 C15 C11 -164.20(16) 3_665 . . . ? Dy2 O3 C8 O4 -13.8(8) 3_565 . . . ? Dy2 O3 C8 C5 164.9(5) 3_565 . . . ? O3 Dy2 O1 C7 11.30(18) 3_565 . . . ? O6 Dy2 O1 C7 151.95(15) 3_665 . . . ? O10 Dy2 O1 C7 -134.97(16) . . . . ? O8 Dy2 O1 C7 -125.79(16) . . . . ? O9 Dy2 O1 C7 78.05(15) . . . . ? O7 Dy2 O1 C7 -59.40(15) . . . . ? O2 Dy2 O1 C7 6.95(14) . . . . ? Dy2 O1 C7 O2 -12.6(2) . . . . ? Dy2 O1 C7 C3 165.3(2) . . . . ? Dy2 O2 C7 O1 12.6(2) . . . . ? Dy2 O2 C7 C3 -165.4(2) . . . . ? C2 C1 C9 C14 -142.8(3) . . . . ? C6 C1 C9 C14 36.9(4) . . . . ? C2 C1 C9 C10 38.0(4) . . . . ? C6 C1 C9 C10 -142.3(3) . . . . ? O3 Dy2 O10 C16 67.9(3) 3_565 . . . ? O6 Dy2 O10 C16 -53.4(2) 3_665 . . . ? O8 Dy2 O10 C16 30.4(2) . . . . ? O9 Dy2 O10 C16 -93.0(3) . . . . ? O7 Dy2 O10 C16 114.2(2) . . . . ? O1 Dy2 O10 C16 -154.8(3) . . . . ? O2 Dy2 O10 C16 172.3(2) . . . . ? O1 C7 C3 C4 -178.0(2) . . . . ? O2 C7 C3 C4 0.0(4) . . . . ? O1 C7 C3 C2 -0.8(4) . . . . ? O2 C7 C3 C2 177.1(2) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C7 C3 C4 C5 177.8(2) . . . . ? C6 C1 C2 C3 1.4(4) . . . . ? C9 C1 C2 C3 -178.8(2) . . . . ? C4 C3 C2 C1 -1.6(4) . . . . ? C7 C3 C2 C1 -178.7(2) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C3 C4 C5 C8 -178.3(2) . . . . ? O3 C8 C5 C4 -6.0(4) . . . . ? O4 C8 C5 C4 172.7(2) . . . . ? O3 C8 C5 C6 175.3(2) . . . . ? O4 C8 C5 C6 -5.9(4) . . . . ? O5 C15 C11 C10 172.2(2) . . . . ? O6 C15 C11 C10 -8.4(4) . . . . ? O5 C15 C11 C12 -6.6(4) . . . . ? O6 C15 C11 C12 172.8(2) . . . . ? C12 C13 C14 C9 -0.3(4) . . . . ? C10 C9 C14 C13 0.0(4) . . . . ? C1 C9 C14 C13 -179.2(2) . . . . ? C12 C11 C10 C9 0.4(4) . . . . ? C15 C11 C10 C9 -178.5(2) . . . . ? C14 C9 C10 C11 0.0(4) . . . . ? C1 C9 C10 C11 179.1(2) . . . . ? Dy2 O10 C16 N1 -168.11(19) . . . . ? C18 N1 C16 O10 176.4(3) . . . . ? C17 N1 C16 O10 -0.5(4) . . . . ? C14 C13 C12 C11 0.7(4) . . . . ? C10 C11 C12 C13 -0.7(4) . . . . ? C15 C11 C12 C13 178.1(2) . . . . ? C4 C5 C6 C1 -0.5(4) . . . . ? C8 C5 C6 C1 178.2(2) . . . . ? C2 C1 C6 C5 -0.4(4) . . . . ? C9 C1 C6 C5 179.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.742 _refine_diff_density_min -0.865 _refine_diff_density_rms 0.121 _database_code_depnum_ccdc_archive 'CCDC 918535' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 Eu N O11' _chemical_formula_weight 580.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 13.694(3) _cell_length_b 7.5770(15) _cell_length_c 21.438(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.27(2) _cell_angle_gamma 90.00 _cell_volume 1994.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3501 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 25.01 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.932 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 3.208 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.3602 _exptl_absorpt_correction_T_max 0.5663 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14692 _diffrn_reflns_av_R_equivalents 0.0710 _diffrn_reflns_av_unetI/netI 0.0497 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3501 _reflns_number_gt 3050 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. we are use 7 restraints as following SIZE 0.2 0.2 0.4 DFIX 1.35 0.001 H9A H9B DFIX 0.85 0.001 H9A O9 H9B O9 DFIX 1.35 0.001 H8A H8B DFIX 0.85 0.001 H8A O8 DFIX 0.85 0.001 H11B O11 DFIX 1.35 0.001 H11A H11B ; _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^)+(0.0434P)^2^+2.2708P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3501 _refine_ls_number_parameters 297 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.111 _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 0.14146(2) 0.73134(3) -0.112291(13) 0.01977(12) Uani 1 1 d . . . O1 O 0.1188(3) 0.5380(5) -0.0264(2) 0.0261(9) Uani 1 1 d . . . O2 O 0.2865(3) 0.5962(6) -0.0073(2) 0.0353(10) Uani 1 1 d . . . O3 O 0.0441(3) 0.2984(7) 0.1620(2) 0.0430(12) Uani 1 1 d . . . O4 O 0.1794(4) 0.2597(6) 0.2664(2) 0.0470(13) Uani 1 1 d . . . O5 O 0.7697(4) 0.2849(6) 0.1846(2) 0.0355(10) Uani 1 1 d . . . O6 O 0.8965(3) 0.2837(6) 0.2943(3) 0.0404(11) Uani 1 1 d . . . O7 O 0.2875(4) 0.9413(6) -0.0619(2) 0.0485(13) Uani 1 1 d . . . O8 O 0.0741(4) 1.0005(6) -0.1783(2) 0.0408(11) Uani 1 1 d D . . H8B H 0.0573 1.0019 -0.2215 0.049 Uiso 1 1 d RD . . O9 O 0.1022(5) 0.4403(6) -0.1640(3) 0.0517(14) Uani 1 1 d D . . O10 O 0.0983(4) 0.9017(6) -0.0314(2) 0.0393(11) Uani 1 1 d . . . H10A H 0.1162 0.8630 0.0094 0.047 Uiso 1 1 d R . . H10B H 0.0653 0.9999 -0.0440 0.047 Uiso 1 1 d R . . N1 N 0.3898(4) 1.1849(7) -0.0483(3) 0.0380(12) Uani 1 1 d . . . C1 C 0.5269(4) 0.4057(7) 0.2467(3) 0.0220(12) Uani 1 1 d . . . C2 C 0.6058(4) 0.3624(7) 0.2254(3) 0.0248(12) Uani 1 1 d . . . H2 H 0.5848 0.3366 0.1788 0.030 Uiso 1 1 calc R . . C3 C 0.7155(4) 0.3567(7) 0.2720(3) 0.0249(12) Uani 1 1 d . . . C4 C 0.7457(5) 0.3997(8) 0.3405(3) 0.0325(14) Uani 1 1 d . . . H4 H 0.8191 0.3988 0.3719 0.039 Uiso 1 1 calc R . . C5 C 0.6697(5) 0.4438(9) 0.3633(3) 0.0375(15) Uani 1 1 d . . . H5 H 0.6915 0.4714 0.4099 0.045 Uiso 1 1 calc R . . C6 C 0.5605(4) 0.4469(8) 0.3167(3) 0.0281(13) Uani 1 1 d . . . H6 H 0.5090 0.4767 0.3321 0.034 Uiso 1 1 calc R . . C7 C 0.8006(5) 0.3044(8) 0.2487(3) 0.0298(13) Uani 1 1 d . . . C8 C 0.4091(4) 0.4097(7) 0.1985(3) 0.0225(12) Uani 1 1 d . . . C9 C 0.3700(4) 0.4692(7) 0.1307(3) 0.0248(12) Uani 1 1 d . . . H9 H 0.4192 0.5098 0.1149 0.030 Uiso 1 1 calc R . . C10 C 0.2592(4) 0.4702(7) 0.0853(3) 0.0246(12) Uani 1 1 d . . . C11 C 0.1851(4) 0.4129(7) 0.1092(3) 0.0241(12) Uani 1 1 d . . . H11 H 0.1110 0.4131 0.0794 0.029 Uiso 1 1 calc R . . C12 C 0.2213(4) 0.3558(7) 0.1768(3) 0.0212(11) Uani 1 1 d . . . C13 C 0.3333(4) 0.3521(7) 0.2208(3) 0.0243(12) Uani 1 1 d . . . H13 H 0.3575 0.3101 0.2660 0.029 Uiso 1 1 calc R . . C14 C 0.2207(4) 0.5363(7) 0.0134(3) 0.0222(12) Uani 1 1 d . . . C15 C 0.1433(5) 0.2984(8) 0.2038(3) 0.0267(12) Uani 1 1 d . . . C16 C 0.3201(6) 1.0636(9) -0.0861(4) 0.0473(18) Uani 1 1 d . . . H16 H 0.2934 1.0703 -0.1341 0.057 Uiso 1 1 calc R . . C17 C 0.4188(7) 1.3309(11) -0.0798(4) 0.061(2) Uani 1 1 d . . . H17A H 0.3786 1.3235 -0.1294 0.091 Uiso 1 1 calc R . . H17B H 0.4954 1.3266 -0.0669 0.091 Uiso 1 1 calc R . . H17C H 0.4019 1.4398 -0.0639 0.091 Uiso 1 1 calc R . . C18 C 0.4372(7) 1.1796(12) 0.0265(4) 0.057(2) Uani 1 1 d . . . H18A H 0.4041 1.2684 0.0428 0.085 Uiso 1 1 calc R . . H18B H 0.5140 1.2014 0.0452 0.085 Uiso 1 1 calc R . . H18C H 0.4252 1.0654 0.0412 0.085 Uiso 1 1 calc R . . O11 O 0.0036(4) 0.2732(5) 0.4439(2) 0.0386(11) Uani 1 1 d D . . H11A H 0.0490 0.2045 0.4742 0.046 Uiso 1 1 d RD . . H11B H 0.009(4) 0.251(6) 0.4066(9) 0.046 Uiso 1 1 d D . . H9A H 0.123(3) 0.366(8) -0.185(3) 0.07(3) Uiso 1 1 d D . . H9B H 0.042(4) 0.400(9) -0.167(5) 0.12(5) Uiso 1 1 d D . . H8A H 0.022(3) 1.053(10) -0.1747(6) 0.08(3) Uiso 1 1 d 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 0.01786(17) 0.02203(18) 0.01902(18) 0.00150(10) 0.00779(12) -0.00038(10) O1 0.022(2) 0.028(2) 0.026(2) 0.0048(17) 0.0085(17) -0.0046(16) O2 0.023(2) 0.053(3) 0.029(2) 0.019(2) 0.0116(19) 0.0029(19) O3 0.018(2) 0.071(3) 0.036(3) 0.015(2) 0.0089(19) -0.002(2) O4 0.029(2) 0.082(4) 0.030(3) 0.017(2) 0.012(2) -0.006(2) O5 0.034(2) 0.046(3) 0.035(3) -0.004(2) 0.023(2) -0.004(2) O6 0.022(2) 0.054(3) 0.046(3) -0.003(2) 0.015(2) 0.005(2) O7 0.046(3) 0.050(3) 0.046(3) 0.005(2) 0.017(2) -0.022(2) O8 0.037(3) 0.037(3) 0.051(3) 0.021(2) 0.021(2) 0.013(2) O9 0.077(4) 0.033(3) 0.072(4) -0.030(3) 0.057(3) -0.023(3) O10 0.058(3) 0.031(2) 0.040(3) 0.005(2) 0.031(2) 0.011(2) N1 0.036(3) 0.039(3) 0.038(3) -0.002(3) 0.015(2) -0.012(3) C1 0.017(3) 0.020(3) 0.029(3) 0.003(2) 0.010(2) -0.001(2) C2 0.028(3) 0.026(3) 0.024(3) -0.004(2) 0.014(2) -0.004(2) C3 0.020(3) 0.027(3) 0.029(3) 0.004(2) 0.012(2) 0.000(2) C4 0.021(3) 0.041(4) 0.030(3) -0.003(3) 0.007(3) 0.003(3) C5 0.029(4) 0.054(4) 0.028(3) -0.002(3) 0.012(3) 0.004(3) C6 0.017(3) 0.037(3) 0.027(3) -0.002(3) 0.007(2) 0.001(2) C7 0.025(3) 0.030(3) 0.039(4) 0.000(3) 0.019(3) -0.004(3) C8 0.019(3) 0.027(3) 0.022(3) -0.001(2) 0.010(2) -0.001(2) C9 0.021(3) 0.023(3) 0.033(3) 0.002(2) 0.015(2) -0.003(2) C10 0.020(3) 0.024(3) 0.026(3) 0.003(2) 0.007(2) 0.004(2) C11 0.021(3) 0.022(3) 0.026(3) 0.000(2) 0.008(2) -0.002(2) C12 0.017(3) 0.021(3) 0.024(3) 0.002(2) 0.008(2) 0.000(2) C13 0.020(3) 0.031(3) 0.018(3) 0.007(2) 0.005(2) 0.006(2) C14 0.024(3) 0.019(3) 0.024(3) 0.000(2) 0.012(2) 0.001(2) C15 0.024(3) 0.031(3) 0.026(3) 0.001(3) 0.012(2) 0.002(3) C16 0.049(4) 0.051(4) 0.036(4) 0.002(3) 0.014(3) -0.016(4) C17 0.081(6) 0.053(5) 0.053(5) -0.004(4) 0.034(4) -0.036(5) C18 0.056(5) 0.067(5) 0.041(4) -0.012(4) 0.015(4) -0.012(4) O11 0.041(3) 0.033(3) 0.041(3) 0.003(2) 0.018(2) 0.0048(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu1 O3 2.291(4) 3_565 ? Eu1 O5 2.359(4) 3_665 ? Eu1 O7 2.405(4) . ? Eu1 O9 2.419(4) . ? Eu1 O8 2.421(4) . ? Eu1 O10 2.435(4) . ? Eu1 O2 2.470(4) . ? Eu1 O1 2.478(4) . ? O1 C14 1.273(7) . ? O2 C14 1.252(6) . ? O3 C15 1.252(7) . ? O3 Eu1 2.291(4) 3_565 ? O4 C15 1.243(7) . ? O5 C7 1.256(7) . ? O5 Eu1 2.359(4) 3_665 ? O6 C7 1.252(7) . ? O7 C16 1.237(8) . ? O8 H8B 0.8499 . ? O8 H8A 0.8500(11) . ? O9 H9A 0.8500(11) . ? O9 H9B 0.8500(11) . ? O10 H10A 0.8501 . ? O10 H10B 0.8500 . ? N1 C16 1.314(8) . ? N1 C18 1.438(9) . ? N1 C17 1.440(8) . ? C1 C2 1.384(7) . ? C1 C6 1.397(8) . ? C1 C8 1.482(7) . ? C2 C3 1.388(8) . ? C2 H2 0.9300 . ? C3 C4 1.377(8) . ? C3 C7 1.510(8) . ? C4 C5 1.373(8) . ? C4 H4 0.9300 . ? C5 C6 1.383(8) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.384(8) . ? C8 C13 1.391(7) . ? C9 C10 1.393(8) . ? C9 H9 0.9300 . ? C10 C11 1.392(7) . ? C10 C14 1.479(7) . ? C11 C12 1.377(7) . ? C11 H11 0.9300 . ? C12 C13 1.401(7) . ? C12 C15 1.489(7) . ? C13 H13 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O11 H11A 0.8500 . ? O11 H11B 0.8499(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Eu1 O5 118.52(16) 3_565 3_665 ? O3 Eu1 O7 143.60(18) 3_565 . ? O5 Eu1 O7 76.18(16) 3_665 . ? O3 Eu1 O9 73.81(19) 3_565 . ? O5 Eu1 O9 74.12(15) 3_665 . ? O7 Eu1 O9 141.31(18) . . ? O3 Eu1 O8 75.73(16) 3_565 . ? O5 Eu1 O8 80.42(15) 3_665 . ? O7 Eu1 O8 74.41(16) . . ? O9 Eu1 O8 123.39(19) . . ? O3 Eu1 O10 79.31(17) 3_565 . ? O5 Eu1 O10 148.62(15) 3_665 . ? O7 Eu1 O10 75.27(16) . . ? O9 Eu1 O10 137.26(15) . . ? O8 Eu1 O10 79.63(15) . . ? O3 Eu1 O2 131.48(14) 3_565 . ? O5 Eu1 O2 97.84(15) 3_665 . ? O7 Eu1 O2 72.03(15) . . ? O9 Eu1 O2 88.02(18) . . ? O8 Eu1 O2 145.77(16) . . ? O10 Eu1 O2 85.52(15) . . ? O3 Eu1 O1 79.04(14) 3_565 . ? O5 Eu1 O1 136.73(14) 3_665 . ? O7 Eu1 O1 114.21(14) . . ? O9 Eu1 O1 74.10(15) . . ? O8 Eu1 O1 142.39(14) . . ? O10 Eu1 O1 68.55(14) . . ? O2 Eu1 O1 52.58(13) . . ? C14 O1 Eu1 92.5(3) . . ? C14 O2 Eu1 93.4(3) . . ? C15 O3 Eu1 164.0(4) . 3_565 ? C7 O5 Eu1 134.8(4) . 3_665 ? C16 O7 Eu1 133.6(5) . . ? Eu1 O8 H8B 119.8 . . ? Eu1 O8 H8A 117(4) . . ? H8B O8 H8A 105.1 . . ? Eu1 O9 H9A 142(4) . . ? Eu1 O9 H9B 112(4) . . ? H9A O9 H9B 105.15(18) . . ? Eu1 O10 H10A 120.0 . . ? Eu1 O10 H10B 120.0 . . ? H10A O10 H10B 120.0 . . ? C16 N1 C18 120.9(6) . . ? C16 N1 C17 121.6(6) . . ? C18 N1 C17 117.5(6) . . ? C2 C1 C6 118.2(5) . . ? C2 C1 C8 122.9(5) . . ? C6 C1 C8 118.9(5) . . ? C1 C2 C3 121.6(5) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C4 C3 C2 118.6(5) . . ? C4 C3 C7 120.2(5) . . ? C2 C3 C7 121.2(5) . . ? C5 C4 C3 121.3(5) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.6(6) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 120.6(5) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O6 C7 O5 124.6(5) . . ? O6 C7 C3 118.1(5) . . ? O5 C7 C3 117.3(5) . . ? C9 C8 C13 117.6(5) . . ? C9 C8 C1 122.3(5) . . ? C13 C8 C1 120.1(5) . . ? C8 C9 C10 122.0(5) . . ? C8 C9 H9 119.0 . . ? C10 C9 H9 119.0 . . ? C11 C10 C9 119.2(5) . . ? C11 C10 C14 120.5(5) . . ? C9 C10 C14 120.3(5) . . ? C12 C11 C10 120.2(5) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 119.5(5) . . ? C11 C12 C15 121.0(5) . . ? C13 C12 C15 119.5(5) . . ? C8 C13 C12 121.5(5) . . ? C8 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? O2 C14 O1 120.4(5) . . ? O2 C14 C10 120.8(5) . . ? O1 C14 C10 118.7(5) . . ? O4 C15 O3 124.0(5) . . ? O4 C15 C12 118.6(5) . . ? O3 C15 C12 117.4(5) . . ? O7 C16 N1 124.4(7) . . ? O7 C16 H16 117.8 . . ? N1 C16 H16 117.8 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? H11A O11 H11B 105.2 . . ? 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 O3 Eu1 O1 C14 -177.9(3) 3_565 . . . ? O5 Eu1 O1 C14 61.8(4) 3_665 . . . ? O7 Eu1 O1 C14 -33.6(3) . . . . ? O9 Eu1 O1 C14 106.0(3) . . . . ? O8 Eu1 O1 C14 -129.4(3) . . . . ? O10 Eu1 O1 C14 -95.2(3) . . . . ? O2 Eu1 O1 C14 6.0(3) . . . . ? O3 Eu1 O2 C14 -11.3(4) 3_565 . . . ? O5 Eu1 O2 C14 -151.2(3) 3_665 . . . ? O7 Eu1 O2 C14 136.1(4) . . . . ? O9 Eu1 O2 C14 -77.6(3) . . . . ? O8 Eu1 O2 C14 124.3(4) . . . . ? O10 Eu1 O2 C14 60.2(3) . . . . ? O1 Eu1 O2 C14 -6.1(3) . . . . ? O3 Eu1 O7 C16 -70.2(7) 3_565 . . . ? O5 Eu1 O7 C16 49.5(7) 3_665 . . . ? O9 Eu1 O7 C16 90.2(7) . . . . ? O8 Eu1 O7 C16 -34.3(7) . . . . ? O10 Eu1 O7 C16 -117.4(7) . . . . ? O2 Eu1 O7 C16 152.6(7) . . . . ? O1 Eu1 O7 C16 -175.2(6) . . . . ? C6 C1 C2 C3 1.1(8) . . . . ? C8 C1 C2 C3 -178.8(5) . . . . ? C1 C2 C3 C4 -1.7(9) . . . . ? C1 C2 C3 C7 178.2(5) . . . . ? C2 C3 C4 C5 1.4(9) . . . . ? C7 C3 C4 C5 -178.5(6) . . . . ? C3 C4 C5 C6 -0.6(10) . . . . ? C4 C5 C6 C1 0.0(10) . . . . ? C2 C1 C6 C5 -0.2(9) . . . . ? C8 C1 C6 C5 179.7(6) . . . . ? Eu1 O5 C7 O6 -16.1(10) 3_665 . . . ? Eu1 O5 C7 C3 163.8(4) 3_665 . . . ? C4 C3 C7 O6 7.3(9) . . . . ? C2 C3 C7 O6 -172.6(5) . . . . ? C4 C3 C7 O5 -172.6(6) . . . . ? C2 C3 C7 O5 7.5(8) . . . . ? C2 C1 C8 C9 -37.4(8) . . . . ? C6 C1 C8 C9 142.7(6) . . . . ? C2 C1 C8 C13 142.4(6) . . . . ? C6 C1 C8 C13 -37.5(8) . . . . ? C13 C8 C9 C10 -0.8(8) . . . . ? C1 C8 C9 C10 179.0(5) . . . . ? C8 C9 C10 C11 1.3(9) . . . . ? C8 C9 C10 C14 179.5(5) . . . . ? C9 C10 C11 C12 -0.1(8) . . . . ? C14 C10 C11 C12 -178.3(5) . . . . ? C10 C11 C12 C13 -1.5(8) . . . . ? C10 C11 C12 C15 178.4(5) . . . . ? C9 C8 C13 C12 -0.8(8) . . . . ? C1 C8 C13 C12 179.4(5) . . . . ? C11 C12 C13 C8 1.9(8) . . . . ? C15 C12 C13 C8 -178.0(5) . . . . ? Eu1 O2 C14 O1 11.1(5) . . . . ? Eu1 O2 C14 C10 -166.0(4) . . . . ? Eu1 O1 C14 O2 -11.0(5) . . . . ? Eu1 O1 C14 C10 166.1(4) . . . . ? C11 C10 C14 O2 176.4(5) . . . . ? C9 C10 C14 O2 -1.8(8) . . . . ? C11 C10 C14 O1 -0.7(8) . . . . ? C9 C10 C14 O1 -178.9(5) . . . . ? Eu1 O3 C15 O4 -4(2) 3_565 . . . ? Eu1 O3 C15 C12 178.3(13) 3_565 . . . ? C11 C12 C15 O4 -175.1(6) . . . . ? C13 C12 C15 O4 4.8(8) . . . . ? C11 C12 C15 O3 2.3(8) . . . . ? C13 C12 C15 O3 -177.8(5) . . . . ? Eu1 O7 C16 N1 167.1(5) . . . . ? C18 N1 C16 O7 2.2(12) . . . . ? C17 N1 C16 O7 -175.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.410 _refine_diff_density_min -0.894 _refine_diff_density_rms 0.143 _database_code_depnum_ccdc_archive 'CCDC 918536' ####################################################################### # # 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_709 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 Gd N O11' _chemical_formula_weight 585.62 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' N N 0.0061 0.0033 '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 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 13.683(3) _cell_length_b 7.6057(15) _cell_length_c 21.533(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.22(2) _cell_angle_gamma 90.00 _cell_volume 2010.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4607 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.63 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.935 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1156 _exptl_absorpt_coefficient_mu 3.362 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3465 _exptl_absorpt_correction_T_max 0.5528 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9269 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_unetI/netI 0.0610 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.63 _reflns_number_total 4607 _reflns_number_gt 3954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. we use 3 restraints are as following SIZE 0.2 0.2 0.4 DFIX 1.35 0.001 H14A H14B DFIX 0.85 0.001 H14A O14 H14B O14 ; _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^)+(0.0496P)^2^+1.1384P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4607 _refine_ls_number_parameters 288 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1023 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 Gd1 Gd 0.641166(18) 0.73162(3) 0.887625(11) 0.01942(10) Uani 1 1 d . . . O1 O 0.7301(4) 0.7142(5) 0.8156(2) 0.0374(10) Uani 1 1 d . . . O2 O 0.6034(3) 0.7163(6) 0.7056(2) 0.0395(10) Uani 1 1 d . . . O3 O 1.2138(3) 0.4023(5) 1.00805(19) 0.0350(9) Uani 1 1 d . . . O4 O 1.3820(3) 0.4612(5) 1.02682(18) 0.0265(8) Uani 1 1 d . . . O5 O 1.4565(3) 0.7011(6) 0.8378(2) 0.0446(11) Uani 1 1 d . . . O6 O 1.3216(4) 0.7405(6) 0.7336(2) 0.0487(13) Uani 1 1 d . . . O7 O 0.5987(4) 0.9014(5) 0.9683(2) 0.0412(11) Uani 1 1 d . . . H7A H 0.5598 0.8564 0.9859 0.049 Uiso 1 1 d R . . H7B H 0.6227 1.0057 0.9789 0.049 Uiso 1 1 d R . . O8 O 0.5734(3) 0.9977(5) 0.8213(2) 0.0396(10) Uani 1 1 d . . . H8A H 0.5519 1.0825 0.8380 0.048 Uiso 1 1 d R . . H8B H 0.5709 1.0066 0.7813 0.048 Uiso 1 1 d R . . O9 O 0.6020(4) 0.4417(5) 0.8365(2) 0.0508(13) Uani 1 1 d . . . H9A H 0.5633 0.3707 0.8467 0.061 Uiso 1 1 d R . . H9B H 0.6271 0.4107 0.8084 0.061 Uiso 1 1 d R . . O10 O 0.7869(4) 0.9395(6) 0.9376(2) 0.0455(11) Uani 1 1 d . . . C18 C 0.8181(6) 1.0643(9) 0.9137(3) 0.0483(17) Uani 1 1 d . . . H18 H 0.7895 1.0740 0.8658 0.058 Uiso 1 1 calc R . . C17 C 0.9171(7) 1.3317(11) 0.9193(4) 0.068(2) Uani 1 1 d . . . H17A H 0.8796 1.3200 0.8699 0.102 Uiso 1 1 calc R . . H17B H 0.9943 1.3326 0.9338 0.102 Uiso 1 1 calc R . . H17C H 0.8958 1.4396 0.9329 0.102 Uiso 1 1 calc R . . C16 C 0.9363(7) 1.1800(11) 1.0262(3) 0.0575(19) Uani 1 1 d . . . H16A H 0.8941 1.2529 1.0417 0.086 Uiso 1 1 calc R . . H16B H 1.0097 1.2233 1.0450 0.086 Uiso 1 1 calc R . . H16C H 0.9365 1.0615 1.0416 0.086 Uiso 1 1 calc R . . N1 N 0.8890(4) 1.1835(7) 0.9517(3) 0.0380(11) Uani 1 1 d . . . C1 C 0.6991(4) 0.6959(7) 0.7511(3) 0.0281(11) Uani 1 1 d . . . C2 C 0.7855(4) 0.6441(7) 0.7281(3) 0.0247(10) Uani 1 1 d . . . C3 C 0.7543(4) 0.6018(7) 0.6589(3) 0.0307(12) Uani 1 1 d . . . H3 H 0.6809 0.6042 0.6276 0.037 Uiso 1 1 calc R . . C4 C 0.8305(5) 0.5567(8) 0.6364(3) 0.0346(13) Uani 1 1 d . . . H4 H 0.8094 0.5291 0.5901 0.042 Uiso 1 1 calc R . . C5 C 0.9389(4) 0.5528(7) 0.6835(3) 0.0288(11) Uani 1 1 d . . . H5 H 0.9904 0.5215 0.6683 0.035 Uiso 1 1 calc R . . C6 C 0.9739(4) 0.5944(6) 0.7533(2) 0.0228(10) Uani 1 1 d . . . C7 C 0.8947(4) 0.6380(7) 0.7752(3) 0.0258(11) Uani 1 1 d . . . H7 H 0.9154 0.6629 0.8216 0.031 Uiso 1 1 calc R . . C8 C 1.0910(4) 0.5906(6) 0.8016(2) 0.0222(10) Uani 1 1 d . . . C9 C 1.1302(4) 0.5310(7) 0.8692(2) 0.0224(10) Uani 1 1 d . . . H9 H 1.0809 0.4901 0.8848 0.027 Uiso 1 1 calc R . . C10 C 1.1676(4) 0.6471(7) 0.7792(3) 0.0247(10) Uani 1 1 d . . . H10 H 1.1438 0.6866 0.7340 0.030 Uiso 1 1 calc R . . C11 C 1.2783(4) 0.6451(6) 0.8232(2) 0.0218(10) Uani 1 1 d . . . C12 C 1.3145(4) 0.5878(6) 0.8910(2) 0.0225(10) Uani 1 1 d . . . H12 H 1.3886 0.5880 0.9208 0.027 Uiso 1 1 calc R . . C13 C 1.2410(4) 0.5304(6) 0.9146(2) 0.0230(10) Uani 1 1 d . . . C14 C 1.2799(4) 0.4632(6) 0.9869(2) 0.0236(10) Uani 1 1 d . . . C15 C 1.3570(4) 0.7009(7) 0.7962(3) 0.0270(11) Uani 1 1 d . . . O14 O 0.5049(4) 0.2256(5) 0.9446(2) 0.0383(10) Uani 1 1 d D . . H14B H 0.474(5) 0.242(6) 0.9011(4) 0.046 Uiso 1 1 d D . . H14A H 0.546(4) 0.314(5) 0.961(2) 0.046 Uiso 1 1 d 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 0.01417(15) 0.02485(15) 0.01942(15) 0.00162(8) 0.00760(11) -0.00040(9) O1 0.028(2) 0.056(3) 0.034(2) -0.0034(19) 0.0192(19) -0.0016(19) O2 0.0142(19) 0.058(3) 0.045(3) -0.005(2) 0.0114(19) 0.0006(18) O3 0.020(2) 0.054(2) 0.032(2) 0.0160(18) 0.0114(17) 0.0006(18) O4 0.0186(18) 0.034(2) 0.0211(17) 0.0013(14) 0.0032(15) -0.0041(15) O5 0.0089(18) 0.077(3) 0.041(2) 0.013(2) 0.0044(17) -0.008(2) O6 0.026(2) 0.089(4) 0.035(2) 0.020(2) 0.017(2) -0.001(2) O7 0.058(3) 0.033(2) 0.049(3) -0.0051(18) 0.038(2) -0.002(2) O8 0.035(2) 0.043(2) 0.046(2) 0.0190(19) 0.022(2) 0.0107(19) O9 0.074(4) 0.037(2) 0.069(3) -0.023(2) 0.057(3) -0.020(2) O10 0.039(3) 0.048(3) 0.046(3) 0.000(2) 0.016(2) -0.020(2) C18 0.044(4) 0.055(4) 0.037(3) 0.001(3) 0.010(3) -0.022(3) C17 0.077(6) 0.064(5) 0.075(5) -0.006(4) 0.045(5) -0.039(5) C16 0.067(5) 0.066(5) 0.036(4) -0.015(4) 0.019(4) -0.016(4) N1 0.036(3) 0.042(3) 0.039(3) -0.008(2) 0.019(2) -0.019(2) C1 0.021(3) 0.029(3) 0.036(3) 0.000(2) 0.014(2) -0.002(2) C2 0.015(2) 0.031(3) 0.030(3) -0.001(2) 0.012(2) -0.001(2) C3 0.011(2) 0.046(3) 0.027(3) -0.002(2) 0.001(2) 0.005(2) C4 0.021(3) 0.052(3) 0.026(3) -0.009(2) 0.005(2) 0.000(3) C5 0.018(3) 0.043(3) 0.028(3) -0.004(2) 0.012(2) 0.002(2) C6 0.016(3) 0.025(2) 0.023(2) 0.0046(19) 0.004(2) 0.0027(19) C7 0.021(3) 0.034(3) 0.025(2) 0.001(2) 0.012(2) 0.000(2) C8 0.014(2) 0.030(3) 0.022(2) 0.0007(19) 0.007(2) 0.0010(19) C9 0.015(2) 0.032(3) 0.023(2) 0.001(2) 0.010(2) -0.0029(19) C10 0.018(2) 0.031(3) 0.025(2) 0.010(2) 0.010(2) 0.005(2) C11 0.019(2) 0.028(2) 0.020(2) 0.0001(19) 0.010(2) -0.002(2) C12 0.011(2) 0.029(3) 0.025(2) 0.0014(19) 0.005(2) 0.0009(19) C13 0.023(3) 0.025(2) 0.021(2) 0.0033(19) 0.011(2) -0.001(2) C14 0.024(3) 0.025(2) 0.022(2) 0.0022(19) 0.010(2) -0.001(2) C15 0.021(3) 0.034(3) 0.028(3) 0.000(2) 0.013(2) 0.000(2) O14 0.035(3) 0.032(2) 0.043(2) -0.0024(18) 0.013(2) -0.0044(18) _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 O5 2.280(4) 1_455 ? Gd1 O1 2.360(4) . ? Gd1 O10 2.396(4) . ? Gd1 O8 2.413(4) . ? Gd1 O9 2.417(4) . ? Gd1 O7 2.432(4) . ? Gd1 O3 2.466(4) 3_767 ? Gd1 O4 2.482(3) 3_767 ? Gd1 C14 2.843(5) 3_767 ? O1 C1 1.268(7) . ? O2 C1 1.251(7) . ? O3 C14 1.266(6) . ? O3 Gd1 2.466(4) 3_767 ? O4 C14 1.276(6) . ? O4 Gd1 2.482(3) 3_767 ? O5 C15 1.255(7) . ? O5 Gd1 2.280(4) 1_655 ? O6 C15 1.251(7) . ? O7 H7A 0.8500 . ? O7 H7B 0.8500 . ? O8 H8A 0.8501 . ? O8 H8B 0.8499 . ? O9 H9A 0.8499 . ? O9 H9B 0.8502 . ? O10 C18 1.242(7) . ? C18 N1 1.316(8) . ? C18 H18 0.9300 . ? C17 N1 1.464(8) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C16 N1 1.441(8) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C1 C2 1.522(7) . ? C2 C7 1.388(7) . ? C2 C3 1.394(7) . ? C3 C4 1.374(7) . ? C3 H3 0.9300 . ? C4 C5 1.378(8) . ? C4 H4 0.9300 . ? C5 C6 1.398(7) . ? C5 H5 0.9300 . ? C6 C7 1.399(7) . ? C6 C8 1.475(7) . ? C7 H7 0.9300 . ? C8 C9 1.388(7) . ? C8 C10 1.400(6) . ? C9 C13 1.395(7) . ? C9 H9 0.9300 . ? C10 C11 1.387(7) . ? C10 H10 0.9300 . ? C11 C12 1.390(6) . ? C11 C15 1.493(7) . ? C12 C13 1.382(6) . ? C12 H12 0.9300 . ? C13 C14 1.495(6) . ? C14 Gd1 2.843(5) 3_767 ? O14 H14B 0.8500(11) . ? O14 H14A 0.8500(11) . ? 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 Gd1 O1 118.11(16) 1_455 . ? O5 Gd1 O10 143.94(17) 1_455 . ? O1 Gd1 O10 76.36(15) . . ? O5 Gd1 O8 75.55(15) 1_455 . ? O1 Gd1 O8 80.41(14) . . ? O10 Gd1 O8 74.84(15) . . ? O5 Gd1 O9 73.52(18) 1_455 . ? O1 Gd1 O9 73.99(14) . . ? O10 Gd1 O9 141.26(16) . . ? O8 Gd1 O9 123.08(17) . . ? O5 Gd1 O7 79.94(17) 1_455 . ? O1 Gd1 O7 148.69(15) . . ? O10 Gd1 O7 75.07(15) . . ? O8 Gd1 O7 80.01(14) . . ? O9 Gd1 O7 137.32(14) . . ? O5 Gd1 O3 131.68(14) 1_455 3_767 ? O1 Gd1 O3 97.74(14) . 3_767 ? O10 Gd1 O3 71.84(15) . 3_767 ? O8 Gd1 O3 146.05(15) . 3_767 ? O9 Gd1 O3 88.00(16) . 3_767 ? O7 Gd1 O3 85.33(14) . 3_767 ? O5 Gd1 O4 79.09(14) 1_455 3_767 ? O1 Gd1 O4 136.59(13) . 3_767 ? O10 Gd1 O4 114.21(13) . 3_767 ? O8 Gd1 O4 142.45(13) . 3_767 ? O9 Gd1 O4 73.96(13) . 3_767 ? O7 Gd1 O4 68.56(13) . 3_767 ? O3 Gd1 O4 52.76(12) 3_767 3_767 ? O5 Gd1 C14 105.70(15) 1_455 3_767 ? O1 Gd1 C14 120.38(15) . 3_767 ? O10 Gd1 C14 91.47(15) . 3_767 ? O8 Gd1 C14 152.20(14) . 3_767 ? O9 Gd1 C14 82.64(15) . 3_767 ? O7 Gd1 C14 73.04(14) . 3_767 ? O3 Gd1 C14 26.39(13) 3_767 3_767 ? O4 Gd1 C14 26.63(13) 3_767 3_767 ? C1 O1 Gd1 134.9(4) . . ? C14 O3 Gd1 93.7(3) . 3_767 ? C14 O4 Gd1 92.7(3) . 3_767 ? C15 O5 Gd1 164.3(4) . 1_655 ? Gd1 O7 H7A 119.9 . . ? Gd1 O7 H7B 120.1 . . ? H7A O7 H7B 120.0 . . ? Gd1 O8 H8A 120.1 . . ? Gd1 O8 H8B 119.9 . . ? H8A O8 H8B 120.0 . . ? Gd1 O9 H9A 120.1 . . ? Gd1 O9 H9B 120.0 . . ? H9A O9 H9B 120.0 . . ? C18 O10 Gd1 133.5(4) . . ? O10 C18 N1 124.2(6) . . ? O10 C18 H18 117.9 . . ? N1 C18 H18 117.9 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 N1 C16 121.6(6) . . ? C18 N1 C17 120.7(6) . . ? C16 N1 C17 117.5(6) . . ? O2 C1 O1 124.8(5) . . ? O2 C1 C2 118.2(5) . . ? O1 C1 C2 117.0(5) . . ? C7 C2 C3 119.7(5) . . ? C7 C2 C1 120.8(4) . . ? C3 C2 C1 119.5(5) . . ? C4 C3 C2 120.8(5) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 118.9(5) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 122.2(5) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C7 117.8(5) . . ? C5 C6 C8 120.2(4) . . ? C7 C6 C8 122.0(5) . . ? C2 C7 C6 120.4(5) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C9 C8 C10 117.5(5) . . ? C9 C8 C6 122.7(4) . . ? C10 C8 C6 119.8(4) . . ? C8 C9 C13 122.1(4) . . ? C8 C9 H9 118.9 . . ? C13 C9 H9 118.9 . . ? C11 C10 C8 121.3(4) . . ? C11 C10 H10 119.4 . . ? C8 C10 H10 119.4 . . ? C10 C11 C12 119.7(4) . . ? C10 C11 C15 119.3(4) . . ? C12 C11 C15 121.0(5) . . ? C13 C12 C11 120.4(5) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C12 C13 C9 119.0(4) . . ? C12 C13 C14 120.5(5) . . ? C9 C13 C14 120.5(4) . . ? O3 C14 O4 119.7(4) . . ? O3 C14 C13 121.1(5) . . ? O4 C14 C13 119.1(4) . . ? O3 C14 Gd1 59.9(3) . 3_767 ? O4 C14 Gd1 60.7(2) . 3_767 ? C13 C14 Gd1 168.1(3) . 3_767 ? O6 C15 O5 123.4(5) . . ? O6 C15 C11 118.9(5) . . ? O5 C15 C11 117.6(5) . . ? H14B O14 H14A 105.15(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Gd1 O1 C1 2.7(6) 1_455 . . . ? O10 Gd1 O1 C1 -141.8(5) . . . . ? O8 Gd1 O1 C1 -65.2(5) . . . . ? O9 Gd1 O1 C1 63.5(5) . . . . ? O7 Gd1 O1 C1 -117.1(5) . . . . ? O3 Gd1 O1 C1 149.1(5) 3_767 . . . ? O4 Gd1 O1 C1 107.3(5) 3_767 . . . ? C14 Gd1 O1 C1 134.6(5) 3_767 . . . ? O5 Gd1 O10 C18 -67.9(7) 1_455 . . . ? O1 Gd1 O10 C18 51.5(6) . . . . ? O8 Gd1 O10 C18 -32.1(6) . . . . ? O9 Gd1 O10 C18 92.4(7) . . . . ? O7 Gd1 O10 C18 -115.5(7) . . . . ? O3 Gd1 O10 C18 154.5(7) 3_767 . . . ? O4 Gd1 O10 C18 -173.2(6) 3_767 . . . ? C14 Gd1 O10 C18 172.5(6) 3_767 . . . ? Gd1 O10 C18 N1 167.6(5) . . . . ? O10 C18 N1 C16 -0.9(12) . . . . ? O10 C18 N1 C17 -176.8(7) . . . . ? Gd1 O1 C1 O2 15.0(9) . . . . ? Gd1 O1 C1 C2 -164.6(3) . . . . ? O2 C1 C2 C7 173.0(5) . . . . ? O1 C1 C2 C7 -7.3(8) . . . . ? O2 C1 C2 C3 -7.2(8) . . . . ? O1 C1 C2 C3 172.4(5) . . . . ? C7 C2 C3 C4 -1.0(9) . . . . ? C1 C2 C3 C4 179.2(5) . . . . ? C2 C3 C4 C5 0.3(9) . . . . ? C3 C4 C5 C6 -0.4(9) . . . . ? C4 C5 C6 C7 1.2(8) . . . . ? C4 C5 C6 C8 -179.2(5) . . . . ? C3 C2 C7 C6 1.8(8) . . . . ? C1 C2 C7 C6 -178.4(5) . . . . ? C5 C6 C7 C2 -1.8(8) . . . . ? C8 C6 C7 C2 178.5(5) . . . . ? C5 C6 C8 C9 -142.1(5) . . . . ? C7 C6 C8 C9 37.5(7) . . . . ? C5 C6 C8 C10 37.3(7) . . . . ? C7 C6 C8 C10 -143.1(5) . . . . ? C10 C8 C9 C13 1.6(8) . . . . ? C6 C8 C9 C13 -179.1(5) . . . . ? C9 C8 C10 C11 -0.6(8) . . . . ? C6 C8 C10 C11 -180.0(5) . . . . ? C8 C10 C11 C12 -0.6(8) . . . . ? C8 C10 C11 C15 177.9(5) . . . . ? C10 C11 C12 C13 0.9(8) . . . . ? C15 C11 C12 C13 -177.6(5) . . . . ? C11 C12 C13 C9 0.0(7) . . . . ? C11 C12 C13 C14 178.0(4) . . . . ? C8 C9 C13 C12 -1.3(8) . . . . ? C8 C9 C13 C14 -179.3(5) . . . . ? Gd1 O3 C14 O4 -10.9(5) 3_767 . . . ? Gd1 O3 C14 C13 166.2(4) 3_767 . . . ? Gd1 O4 C14 O3 10.9(5) 3_767 . . . ? Gd1 O4 C14 C13 -166.4(4) 3_767 . . . ? C12 C13 C14 O3 -176.5(5) . . . . ? C9 C13 C14 O3 1.5(8) . . . . ? C12 C13 C14 O4 0.7(7) . . . . ? C9 C13 C14 O4 178.7(5) . . . . ? C12 C13 C14 Gd1 -84.9(18) . . . 3_767 ? C9 C13 C14 Gd1 93.1(18) . . . 3_767 ? Gd1 O5 C15 O6 5(2) 1_655 . . . ? Gd1 O5 C15 C11 -176.9(13) 1_655 . . . ? C10 C11 C15 O6 -3.3(8) . . . . ? C12 C11 C15 O6 175.3(5) . . . . ? C10 C11 C15 O5 178.5(5) . . . . ? C12 C11 C15 O5 -2.9(8) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 1.659 _refine_diff_density_min -1.985 _refine_diff_density_rms 0.156 _database_code_depnum_ccdc_archive 'CCDC 918537' ####################################################################### # # 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_1 #TrackingRef 'La.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H23 La O14' _chemical_formula_weight 566.24 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' La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.216(7) _cell_length_b 7.5350(18) _cell_length_c 21.379(5) _cell_angle_alpha 90.00 _cell_angle_beta 115.320(3) _cell_angle_gamma 90.00 _cell_volume 3963.1(17) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4697 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 27.9 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.898 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 2.229 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.4692 _exptl_absorpt_correction_T_max 0.6641 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19401 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.90 _reflns_number_total 4697 _reflns_number_gt 4108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0359P)^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 NONE _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4697 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0713 _refine_ls_wR_factor_gt 0.0704 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0.120 _refine_ls_shift/su_mean 0.002 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 La1 La 0.924261(5) 0.297572(19) 0.617400(7) 0.00699(6) Uani 1 1 d . . . O2 O 0.55093(8) 0.2924(2) 0.68881(11) 0.0138(4) Uani 1 1 d . . . O3 O 0.61386(8) 0.2935(2) 0.79769(11) 0.0153(4) Uani 1 1 d . . . O5 O 0.84814(7) 0.0620(3) 0.60079(10) 0.0156(4) Uani 1 1 d . . . O6 O 0.84205(7) 0.5065(3) 0.60816(10) 0.0160(4) Uani 1 1 d . . . O7 O 0.91535(8) 0.2793(3) 0.72712(10) 0.0149(4) Uani 1 1 d . . . O8 O 0.95629(9) 0.5959(3) 0.67176(13) 0.0316(6) Uani 1 1 d . . . H8A H 0.9612 0.6663 0.6427 0.047 Uiso 1 1 d R . . H8B H 0.9323 0.6434 0.6835 0.047 Uiso 1 1 d R . . O9 O 0.96597(8) 0.0077(3) 0.67683(10) 0.0189(5) Uani 1 1 d . . . H9A H 0.9406 -0.0689 0.6738 0.028 Uiso 1 1 d R . . H9B H 0.9855 -0.0404 0.6573 0.028 Uiso 1 1 d R . . O10 O 0.92715(7) 0.5146(2) 1.01934(9) 0.0123(4) Uani 1 1 d . . . O11 O 0.84957(7) 0.6568(3) 0.98900(10) 0.0115(4) Uani 1 1 d . . . C12 C 0.59864(11) 0.3209(3) 0.73334(15) 0.0104(5) Uani 1 1 d . . . O13 O 0.95234(7) 0.1101(3) 0.53713(10) 0.0157(4) Uani 1 1 d . . . H13A H 0.9664 0.0108 0.5570 0.024 Uiso 1 1 d R . . H13B H 0.9242 0.0878 0.4989 0.024 Uiso 1 1 d R . . O15 O 0.97820(8) 0.3283(3) 0.83399(11) 0.0227(5) Uani 1 1 d . . . C16 C 0.93010(11) 0.3270(3) 0.78945(14) 0.0102(5) Uani 1 1 d . . . C17 C 0.64002(10) 0.3901(3) 0.71054(13) 0.0086(5) Uani 1 1 d . . . C18 C 0.69491(10) 0.3925(3) 0.75638(13) 0.0095(5) Uani 1 1 d . . . H18 H 0.7055 0.3550 0.8018 0.011 Uiso 1 1 calc R . . C19 C 0.79302(10) 0.4471(3) 0.78546(13) 0.0089(5) Uani 1 1 d . . . C20 C 0.83257(9) 0.3901(3) 0.76461(13) 0.0090(5) Uani 1 1 d . . . H20 H 0.8224 0.3544 0.7191 0.011 Uiso 1 1 calc R . . C21 C 0.73426(10) 0.4497(3) 0.73568(13) 0.0089(5) Uani 1 1 d . . . C22 C 0.88726(10) 0.3862(3) 0.81159(13) 0.0081(5) Uani 1 1 d . . . C24 C 0.62446(10) 0.4517(3) 0.64320(14) 0.0117(6) Uani 1 1 d . . . H24 H 0.5879 0.4525 0.6123 0.014 Uiso 1 1 calc R . . C25 C 0.88076(10) 0.5599(3) 0.97367(13) 0.0096(5) Uani 1 1 d . . . C26 C 0.80913(10) 0.5019(3) 0.85364(13) 0.0096(5) Uani 1 1 d . . . H26 H 0.7831 0.5418 0.8677 0.011 Uiso 1 1 calc R . . C27 C 0.86345(10) 0.4978(3) 0.90089(13) 0.0086(5) Uani 1 1 d . . . C28 C 0.90239(10) 0.4388(3) 0.87976(13) 0.0100(5) Uani 1 1 d . . . H28 H 0.9388 0.4344 0.9114 0.012 Uiso 1 1 calc R . . C29 C 0.66293(10) 0.5117(4) 0.62209(14) 0.0125(6) Uani 1 1 d . . . H29 H 0.6522 0.5537 0.5773 0.015 Uiso 1 1 calc R . . C35 C 0.71751(10) 0.5092(4) 0.66792(14) 0.0118(5) Uani 1 1 d . . . H35 H 0.7433 0.5477 0.6532 0.014 Uiso 1 1 calc R . . O1 O 0.99446(7) 0.7735(2) 0.54491(9) 0.0139(4) Uani 1 1 d G . . H1A H 1.0055 0.7954 0.5141 0.021 Uiso 1 1 d G . . O14 O 0.74408(8) 0.7639(2) 0.93362(10) 0.0243(5) Uani 1 1 d G . . O33 O 0.69778(11) 0.2623(3) 0.99639(13) 0.0514(8) Uani 1 1 d G . . H33A H 0.6907 0.3523 0.9700 0.077 Uiso 1 1 d G . . H33B H 0.6850 0.2776 1.0259 0.077 Uiso 1 1 d G . . H1B H 0.9752 0.6803 0.5312 0.077 Uiso 1 1 d R . . H5B H 0.8543 -0.0159 0.6318 0.077 Uiso 1 1 d R . . H6A H 0.8111 0.4594 0.5983 0.077 Uiso 1 1 d R . . H5A H 0.8174 0.1062 0.5936 0.077 Uiso 1 1 d R . . H6B H 0.8462 0.5969 0.6195 0.077 Uiso 1 1 d R . . H14A H 0.7765 0.7518 0.9383 0.077 Uiso 1 1 d R . . H14B H 0.7500 0.7126 0.9014 0.077 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 La1 0.00538(9) 0.01081(9) 0.00493(9) 0.00070(5) 0.00234(7) -0.00031(5) O2 0.0072(9) 0.0180(11) 0.0163(11) -0.0028(8) 0.0051(8) -0.0034(7) O3 0.0181(11) 0.0181(11) 0.0130(10) -0.0006(8) 0.0097(9) -0.0049(8) O5 0.0136(10) 0.0164(10) 0.0156(10) 0.0029(8) 0.0051(8) -0.0029(8) O6 0.0150(10) 0.0154(10) 0.0173(10) -0.0024(8) 0.0066(8) 0.0018(8) O7 0.0136(10) 0.0247(11) 0.0096(10) -0.0003(8) 0.0080(9) 0.0022(8) O8 0.0333(13) 0.0285(13) 0.0484(16) -0.0228(12) 0.0322(12) -0.0175(11) O9 0.0147(10) 0.0246(12) 0.0236(11) 0.0115(9) 0.0140(9) 0.0070(8) O10 0.0096(9) 0.0152(10) 0.0091(9) -0.0030(8) 0.0012(7) 0.0032(7) O11 0.0091(9) 0.0176(10) 0.0079(9) -0.0032(7) 0.0036(8) 0.0017(8) C12 0.0128(13) 0.0080(13) 0.0122(13) -0.0013(10) 0.0071(11) 0.0014(10) O13 0.0176(10) 0.0158(10) 0.0139(10) 0.0002(8) 0.0068(8) 0.0026(8) O15 0.0067(10) 0.0433(14) 0.0150(11) -0.0085(10) 0.0019(8) 0.0025(9) C16 0.0106(13) 0.0095(12) 0.0121(13) -0.0002(10) 0.0065(11) 0.0002(10) C17 0.0085(12) 0.0079(12) 0.0098(12) -0.0026(10) 0.0043(10) -0.0007(10) C18 0.0120(12) 0.0085(12) 0.0086(12) 0.0006(10) 0.0050(10) 0.0016(10) C19 0.0090(12) 0.0095(13) 0.0088(13) 0.0014(10) 0.0045(10) -0.0012(10) C20 0.0107(12) 0.0086(12) 0.0076(12) 0.0001(10) 0.0039(10) -0.0009(10) C21 0.0074(12) 0.0098(13) 0.0091(13) -0.0028(10) 0.0031(10) 0.0000(9) C22 0.0091(12) 0.0069(12) 0.0104(13) -0.0007(10) 0.0063(10) -0.0016(10) C24 0.0065(12) 0.0142(13) 0.0113(13) -0.0015(10) 0.0009(10) -0.0015(10) C25 0.0114(12) 0.0084(12) 0.0097(13) -0.0013(10) 0.0051(11) -0.0032(10) C26 0.0099(12) 0.0107(13) 0.0101(13) -0.0019(10) 0.0061(10) -0.0011(10) C27 0.0107(12) 0.0082(12) 0.0081(12) -0.0013(10) 0.0051(10) -0.0012(10) C28 0.0085(12) 0.0103(13) 0.0088(12) 0.0002(10) 0.0014(10) -0.0016(10) C29 0.0134(13) 0.0159(14) 0.0075(12) 0.0011(10) 0.0038(11) -0.0001(11) C35 0.0118(13) 0.0144(13) 0.0123(13) -0.0021(11) 0.0081(11) -0.0028(10) O1 0.0171(10) 0.0123(10) 0.0159(11) -0.0006(8) 0.0104(9) -0.0043(8) O14 0.0149(11) 0.0381(13) 0.0201(12) 0.0001(10) 0.0076(10) 0.0006(10) O33 0.061(2) 0.0595(19) 0.0352(17) 0.0074(15) 0.0216(16) 0.0020(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag La1 O15 2.413(2) 2_756 ? La1 O7 2.463(2) . ? La1 O8 2.509(2) . ? La1 O9 2.538(2) . ? La1 O10 2.5584(19) 6_565 ? La1 O13 2.5780(19) . ? La1 O5 2.6344(19) . ? La1 O11 2.6482(19) 6_565 ? La1 O6 2.6733(19) . ? La1 C25 2.981(3) 6_565 ? O2 C12 1.257(3) . ? O3 C12 1.273(3) . ? O5 H5B 0.8473 . ? O5 H5A 0.8523 . ? O6 H6A 0.8536 . ? O6 H6B 0.7153 . ? O7 C16 1.269(3) . ? O8 H8A 0.8703 . ? O8 H8B 0.8701 . ? O9 H9A 0.8809 . ? O9 H9B 0.8806 . ? O10 C25 1.269(3) . ? O10 La1 2.5584(19) 6_566 ? O11 C25 1.264(3) . ? O11 La1 2.6482(19) 6_566 ? C12 C17 1.499(4) . ? O13 H13A 0.8643 . ? O13 H13B 0.8645 . ? O15 C16 1.247(3) . ? O15 La1 2.413(2) 2_756 ? C16 C22 1.501(4) . ? C17 C24 1.395(4) . ? C17 C18 1.393(3) . ? C18 C21 1.391(4) . ? C18 H18 0.9300 . ? C19 C26 1.393(3) . ? C19 C20 1.397(4) . ? C19 C21 1.495(3) . ? C20 C22 1.395(3) . ? C20 H20 0.9300 . ? C21 C35 1.394(4) . ? C22 C28 1.392(3) . ? C24 C29 1.382(4) . ? C24 H24 0.9300 . ? C25 C27 1.495(3) . ? C25 La1 2.981(3) 6_566 ? C26 C27 1.389(3) . ? C26 H26 0.9300 . ? C27 C28 1.391(4) . ? C28 H28 0.9300 . ? C29 C35 1.386(4) . ? C29 H29 0.9300 . ? C35 H35 0.9300 . ? O1 H1A 0.8497 . ? O1 H1B 0.8497 . ? O14 H14B 0.8643 . ? O14 H14A 0.8500 . ? O14 H14B 0.8643 . ? O33 H33A 0.8500 . ? O33 H33B 0.8501 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O15 La1 O7 97.67(7) 2_756 . ? O15 La1 O8 67.31(8) 2_756 . ? O7 La1 O8 76.43(7) . . ? O15 La1 O9 72.10(7) 2_756 . ? O7 La1 O9 71.34(7) . . ? O8 La1 O9 123.14(8) . . ? O15 La1 O10 83.46(6) 2_756 6_565 ? O7 La1 O10 149.47(6) . 6_565 ? O8 La1 O10 75.97(7) . 6_565 ? O9 La1 O10 136.27(6) . 6_565 ? O15 La1 O13 75.79(7) 2_756 . ? O7 La1 O13 141.37(6) . . ? O8 La1 O13 131.00(7) . . ? O9 La1 O13 70.44(7) . . ? O10 La1 O13 68.66(7) 6_565 . ? O15 La1 O5 141.23(7) 2_756 . ? O7 La1 O5 72.45(6) . . ? O8 La1 O5 139.77(7) . . ? O9 La1 O5 69.21(6) . . ? O10 La1 O5 124.08(6) 6_565 . ? O13 La1 O5 88.91(6) . . ? O15 La1 O11 130.50(7) 2_756 6_565 ? O7 La1 O11 130.53(6) . 6_565 ? O8 La1 O11 108.93(7) . 6_565 ? O9 La1 O11 127.70(6) . 6_565 ? O10 La1 O11 50.03(6) 6_565 6_565 ? O13 La1 O11 72.29(6) . 6_565 ? O5 La1 O11 74.76(6) . 6_565 ? O15 La1 O6 135.01(7) 2_756 . ? O7 La1 O6 71.53(6) . . ? O8 La1 O6 67.70(7) . . ? O9 La1 O6 136.47(6) . . ? O10 La1 O6 86.08(6) 6_565 . ? O13 La1 O6 138.64(6) . . ? O5 La1 O6 78.57(7) . . ? O11 La1 O6 66.41(6) 6_565 . ? O15 La1 C25 106.75(7) 2_756 6_565 ? O7 La1 C25 147.61(7) . 6_565 ? O8 La1 C25 93.48(8) . 6_565 ? O9 La1 C25 136.20(7) . 6_565 ? O10 La1 C25 25.01(6) 6_565 6_565 ? O13 La1 C25 67.14(7) . 6_565 ? O5 La1 C25 99.27(6) . 6_565 ? O11 La1 C25 25.08(6) 6_565 6_565 ? O6 La1 C25 76.15(6) . 6_565 ? La1 O5 H5B 118.8 . . ? La1 O5 H5A 114.6 . . ? H5B O5 H5A 105.2 . . ? La1 O6 H6A 118.7 . . ? La1 O6 H6B 121.9 . . ? H6A O6 H6B 118.5 . . ? C16 O7 La1 150.31(18) . . ? La1 O8 H8A 110.1 . . ? La1 O8 H8B 110.3 . . ? H8A O8 H8B 108.5 . . ? La1 O9 H9A 111.0 . . ? La1 O9 H9B 110.4 . . ? H9A O9 H9B 107.9 . . ? C25 O10 La1 96.47(15) . 6_566 ? C25 O11 La1 92.35(15) . 6_566 ? O2 C12 O3 123.0(3) . . ? O2 C12 C17 119.3(3) . . ? O3 C12 C17 117.7(2) . . ? La1 O13 H13A 110.0 . . ? La1 O13 H13B 110.0 . . ? H13A O13 H13B 108.9 . . ? C16 O15 La1 158.6(2) . 2_756 ? O15 C16 O7 124.2(3) . . ? O15 C16 C22 117.4(2) . . ? O7 C16 C22 118.4(2) . . ? C24 C17 C18 118.9(2) . . ? C24 C17 C12 120.8(2) . . ? C18 C17 C12 120.3(2) . . ? C21 C18 C17 121.3(2) . . ? C21 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C26 C19 C20 119.0(2) . . ? C26 C19 C21 120.2(2) . . ? C20 C19 C21 120.8(2) . . ? C22 C20 C19 120.5(2) . . ? C22 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C18 C21 C35 118.5(2) . . ? C18 C21 C19 120.3(2) . . ? C35 C21 C19 121.3(2) . . ? C28 C22 C20 119.7(2) . . ? C28 C22 C16 119.5(2) . . ? C20 C22 C16 120.8(2) . . ? C29 C24 C17 120.5(2) . . ? C29 C24 H24 119.7 . . ? C17 C24 H24 119.7 . . ? O11 C25 O10 120.9(2) . . ? O11 C25 C27 120.2(2) . . ? O10 C25 C27 118.9(2) . . ? O11 C25 La1 62.58(14) . 6_566 ? O10 C25 La1 58.52(13) . 6_566 ? C27 C25 La1 174.33(17) . 6_566 ? C27 C26 C19 121.0(2) . . ? C27 C26 H26 119.5 . . ? C19 C26 H26 119.5 . . ? C26 C27 C28 119.5(2) . . ? C26 C27 C25 120.9(2) . . ? C28 C27 C25 119.6(2) . . ? C27 C28 C22 120.4(2) . . ? C27 C28 H28 119.8 . . ? C22 C28 H28 119.8 . . ? C24 C29 C35 119.8(3) . . ? C24 C29 H29 120.1 . . ? C35 C29 H29 120.1 . . ? C29 C35 C21 121.0(3) . . ? C29 C35 H35 119.5 . . ? C21 C35 H35 119.5 . . ? H1A O1 H1B 105.2 . . ? H14B O14 H14A 60.4 . . ? H14B O14 H14B 0.0 . . ? H14A O14 H14B 60.4 . . ? H33A O33 H33B 109.6 . . ? 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 O15 La1 O7 C16 37.1(4) 2_756 . . . ? O8 La1 O7 C16 -27.2(4) . . . . ? O9 La1 O7 C16 105.2(4) . . . . ? O10 La1 O7 C16 -53.0(4) 6_565 . . . ? O13 La1 O7 C16 113.9(4) . . . . ? O5 La1 O7 C16 178.6(4) . . . . ? O11 La1 O7 C16 -130.7(3) 6_565 . . . ? O6 La1 O7 C16 -97.9(4) . . . . ? C25 La1 O7 C16 -101.9(4) 6_565 . . . ? La1 O15 C16 O7 3.4(8) 2_756 . . . ? La1 O15 C16 C22 -176.6(4) 2_756 . . . ? La1 O7 C16 O15 -50.6(5) . . . . ? La1 O7 C16 C22 129.4(3) . . . . ? O2 C12 C17 C24 11.1(4) . . . . ? O3 C12 C17 C24 -168.9(2) . . . . ? O2 C12 C17 C18 -168.4(2) . . . . ? O3 C12 C17 C18 11.5(4) . . . . ? C24 C17 C18 C21 -2.0(4) . . . . ? C12 C17 C18 C21 177.5(2) . . . . ? C26 C19 C20 C22 0.7(4) . . . . ? C21 C19 C20 C22 -179.3(2) . . . . ? C17 C18 C21 C35 1.5(4) . . . . ? C17 C18 C21 C19 -178.6(2) . . . . ? C26 C19 C21 C18 -42.0(4) . . . . ? C20 C19 C21 C18 137.9(3) . . . . ? C26 C19 C21 C35 137.9(3) . . . . ? C20 C19 C21 C35 -42.1(4) . . . . ? C19 C20 C22 C28 0.3(4) . . . . ? C19 C20 C22 C16 -179.3(2) . . . . ? O15 C16 C22 C28 -0.2(4) . . . . ? O7 C16 C22 C28 179.8(2) . . . . ? O15 C16 C22 C20 179.4(3) . . . . ? O7 C16 C22 C20 -0.5(4) . . . . ? C18 C17 C24 C29 0.9(4) . . . . ? C12 C17 C24 C29 -178.6(2) . . . . ? La1 O11 C25 O10 5.2(3) 6_566 . . . ? La1 O11 C25 C27 -174.3(2) 6_566 . . . ? La1 O10 C25 O11 -5.5(3) 6_566 . . . ? La1 O10 C25 C27 174.1(2) 6_566 . . . ? C20 C19 C26 C27 -1.0(4) . . . . ? C21 C19 C26 C27 179.0(2) . . . . ? C19 C26 C27 C28 0.3(4) . . . . ? C19 C26 C27 C25 178.8(2) . . . . ? O11 C25 C27 C26 -17.8(4) . . . . ? O10 C25 C27 C26 162.6(2) . . . . ? La1 C25 C27 C26 -135.5(17) 6_566 . . . ? O11 C25 C27 C28 160.8(2) . . . . ? O10 C25 C27 C28 -18.8(4) . . . . ? La1 C25 C27 C28 43(2) 6_566 . . . ? C26 C27 C28 C22 0.8(4) . . . . ? C25 C27 C28 C22 -177.8(2) . . . . ? C20 C22 C28 C27 -1.1(4) . . . . ? C16 C22 C28 C27 178.6(2) . . . . ? C17 C24 C29 C35 0.6(4) . . . . ? C24 C29 C35 C21 -1.2(4) . . . . ? C18 C21 C35 C29 0.1(4) . . . . ? C19 C21 C35 C29 -179.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.865 _refine_diff_density_min -1.042 _refine_diff_density_rms 0.135 _database_code_depnum_ccdc_archive 'CCDC 918538' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 Nd O12.75' _chemical_formula_weight 547.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.270(5) _cell_length_b 7.6022(15) _cell_length_c 21.167(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.12(3) _cell_angle_gamma 90.00 _cell_volume 3973.1(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3449 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 25.01 _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2168 _exptl_absorpt_coefficient_mu 2.678 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5541 _exptl_absorpt_correction_T_max 0.6165 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 14063 _diffrn_reflns_av_R_equivalents 0.1008 _diffrn_reflns_av_unetI/netI 0.0752 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3449 _reflns_number_gt 2930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. we use 9 restraints are as following SIZE 0.25 0.2 0.22 ISOR O7 DFIX 1.39 0.01 H9a H9b DFIX 0.85 0.01 O9 H9b O9 H9a OMIT 10 2 9 OMIT 18 2 7 OMIT 4 2 0 OMIT 0 0 4 OMIT -3.00 50.02 ; _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^)+(0.0614P)^2^+48.1206P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3449 _refine_ls_number_parameters 275 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1395 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Nd1 Nd 0.073912(15) 0.20470(6) -0.11840(2) 0.02627(19) Uani 1 1 d . . . O3 O 0.0683(2) 0.0175(8) -0.0237(3) 0.0392(14) Uani 1 1 d . . . O4 O 0.3833(3) -0.1941(9) 0.1975(3) 0.0474(17) Uani 1 1 d . . . O5 O 0.4457(2) -0.1937(9) 0.3065(4) 0.0486(18) Uani 1 1 d . . . O6 O 0.0497(3) 0.3839(8) -0.0359(3) 0.0418(15) Uani 1 1 d . . . H6A H 0.0311 0.3203 -0.0190 0.063 Uiso 1 1 d R . . H6B H 0.0356 0.4860 -0.0439 0.063 Uiso 1 1 d R . . O9 O 0.0370(3) 0.4984(9) -0.1713(4) 0.0513(18) Uani 1 1 d D . . H9A H 0.0107 0.5683 -0.1803 0.077 Uiso 1 1 d RD . . H9B H 0.0625 0.5503 -0.1769 0.077 Uiso 1 1 d RD . . O12 O 0.1472(2) 0.1439(9) 0.0052(3) 0.0401(15) Uani 1 1 d . . . O13 O 0.0204(2) -0.1760(10) 0.1671(3) 0.0489(18) Uani 1 1 d . . . O15 O 0.0828(3) -0.2175(9) 0.2726(3) 0.0439(16) Uani 1 1 d . . . O21 O 0.1500(2) 0.4174(9) -0.0978(3) 0.0494(17) Uani 1 1 d . . . H21A H 0.1762 0.3635 -0.1007 0.074 Uiso 1 1 d R . . H21B H 0.1394 0.5001 -0.1277 0.074 Uiso 1 1 d R . . O28 O 0.0430(4) -0.0896(11) -0.1745(5) 0.079(3) Uani 1 1 d . . . H28A H 0.0160 -0.1270 -0.1670 0.118 Uiso 1 1 d R . . H28B H 0.0691 -0.1647 -0.1574 0.118 Uiso 1 1 d R . . C1 C 0.3021(3) -0.1063(11) 0.2400(4) 0.0328(18) Uani 1 1 d . . . H1 H 0.2921 -0.1376 0.1937 0.039 Uiso 1 1 calc R . . C10 C 0.1871(3) -0.0044(11) 0.1424(4) 0.0300(17) Uani 1 1 d . . . H10 H 0.2126 0.0360 0.1274 0.036 Uiso 1 1 calc R . . C11 C 0.2620(3) -0.0577(10) 0.2614(4) 0.0284(17) Uani 1 1 d . . . C14 C 0.1647(3) -0.1170(11) 0.2326(4) 0.0286(17) Uani 1 1 d . . . H14 H 0.1750 -0.1553 0.2782 0.034 Uiso 1 1 calc R . . C16 C 0.3982(4) -0.1697(11) 0.2623(5) 0.036(2) Uani 1 1 d . . . C17 C 0.3319(3) -0.0036(13) 0.3760(4) 0.044(2) Uani 1 1 d . . . H17 H 0.3418 0.0324 0.4218 0.053 Uiso 1 1 calc R . . C18 C 0.2042(3) -0.0590(10) 0.2117(4) 0.0267(16) Uani 1 1 d . . . C19 C 0.1331(3) -0.0092(11) 0.0957(4) 0.0277(17) Uani 1 1 d . . . C20 C 0.1152(3) 0.0554(11) 0.0216(4) 0.0322(18) Uani 1 1 d . . . C23 C 0.2779(3) -0.0058(13) 0.3292(4) 0.040(2) Uani 1 1 d . . . H23 H 0.2518 0.0287 0.3441 0.048 Uiso 1 1 calc R . . C25 C 0.0946(3) -0.0680(11) 0.1180(4) 0.0288(17) Uani 1 1 d . . . H25 H 0.0583 -0.0735 0.0869 0.035 Uiso 1 1 calc R . . C27 C 0.1110(3) -0.1182(11) 0.1869(4) 0.0270(16) Uani 1 1 d . . . C30 C 0.3710(3) -0.0550(12) 0.3545(5) 0.038(2) Uani 1 1 d . . . H30 H 0.4073 -0.0537 0.3859 0.045 Uiso 1 1 calc R . . C31 C 0.3559(3) -0.1086(11) 0.2862(4) 0.0308(17) Uani 1 1 d . . . C32 C 0.0682(3) -0.1756(10) 0.2109(4) 0.0304(18) Uani 1 1 d . . . O26 O 0.1525(3) -0.0030(11) -0.1122(4) 0.073(2) Uani 1 1 d . . . H26A H 0.1821 0.0544 -0.0968 0.110 Uiso 1 1 d R . . H26B H 0.1455 -0.0415 -0.1529 0.110 Uiso 1 1 d R . . O1 O 0.0037(3) 0.7218(9) 0.9516(4) 0.0444(16) Uani 1 1 d G . . H1A H -0.0158 0.7204 0.9078 0.067 Uiso 1 1 d G . . H1B H 0.0240 0.8121 0.9622 0.067 Uiso 1 1 d G . . O2 O 0.2455(5) 0.236(2) 0.9358(8) 0.060(4) Uani 0.50 1 d P . . O7 O 0.2311(18) 0.778(4) 0.0181(16) 0.086(13) Uani 0.25 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 Nd1 0.0244(3) 0.0317(3) 0.0249(3) 0.00230(16) 0.0126(2) -0.00129(17) O3 0.034(3) 0.048(4) 0.033(3) 0.012(3) 0.011(3) -0.009(3) O4 0.044(4) 0.062(5) 0.040(4) -0.002(3) 0.022(3) 0.007(3) O5 0.024(3) 0.072(5) 0.052(4) 0.002(3) 0.018(3) 0.004(3) O6 0.060(4) 0.035(3) 0.044(3) -0.005(3) 0.036(3) 0.001(3) O9 0.051(4) 0.047(4) 0.074(5) 0.025(4) 0.043(4) 0.025(3) O12 0.028(3) 0.057(4) 0.035(3) 0.013(3) 0.013(3) -0.007(3) O13 0.021(3) 0.085(5) 0.039(4) 0.004(3) 0.012(3) -0.013(3) O15 0.038(4) 0.072(5) 0.030(3) 0.009(3) 0.023(3) 0.000(3) O21 0.039(3) 0.054(4) 0.049(4) 0.009(3) 0.012(3) -0.011(3) O28 0.104(7) 0.057(5) 0.110(7) -0.013(5) 0.079(6) -0.012(5) C1 0.025(4) 0.039(5) 0.035(4) 0.003(4) 0.013(3) -0.001(4) C10 0.025(4) 0.032(4) 0.039(4) 0.007(4) 0.020(3) 0.002(3) C11 0.028(4) 0.027(4) 0.035(4) 0.008(3) 0.017(3) 0.002(3) C14 0.025(4) 0.033(4) 0.028(4) 0.006(3) 0.012(3) 0.005(3) C16 0.032(5) 0.028(4) 0.055(6) 0.002(4) 0.027(4) -0.003(4) C17 0.038(5) 0.057(6) 0.029(4) -0.008(4) 0.007(4) 0.003(4) C18 0.021(4) 0.027(4) 0.037(4) -0.004(3) 0.016(3) 0.005(3) C19 0.022(4) 0.032(4) 0.028(4) 0.002(3) 0.009(3) 0.001(3) C20 0.031(4) 0.036(5) 0.033(4) 0.008(4) 0.018(4) 0.007(4) C23 0.034(4) 0.055(6) 0.034(4) 0.005(4) 0.018(4) 0.013(4) C25 0.028(4) 0.033(4) 0.026(4) 0.005(3) 0.012(3) 0.002(3) C27 0.027(4) 0.032(4) 0.028(4) 0.000(3) 0.018(3) 0.003(3) C30 0.025(4) 0.040(5) 0.041(5) -0.002(4) 0.008(4) 0.003(4) C31 0.026(4) 0.029(4) 0.037(4) 0.004(4) 0.013(3) -0.001(3) C32 0.037(5) 0.026(4) 0.037(5) -0.004(3) 0.025(4) -0.003(3) O26 0.071(5) 0.079(6) 0.072(5) -0.009(4) 0.032(4) 0.015(5) O1 0.050(4) 0.039(4) 0.048(4) -0.004(3) 0.024(3) -0.010(3) O2 0.028(7) 0.087(11) 0.063(10) -0.008(8) 0.017(7) -0.011(7) O7 0.17(4) 0.08(2) 0.041(17) 0.018(15) 0.07(2) 0.05(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 Nd1 O13 2.339(6) 5 ? Nd1 O15 2.421(6) 6 ? Nd1 O28 2.505(8) . ? Nd1 O9 2.509(6) . ? Nd1 O6 2.514(5) . ? Nd1 O3 2.516(5) . ? Nd1 O21 2.517(6) . ? Nd1 O12 2.572(6) . ? Nd1 O26 2.619(7) . ? Nd1 C20 2.916(8) . ? O3 C20 1.263(10) . ? O4 C16 1.267(11) . ? O5 C16 1.247(11) . ? O6 H6A 0.8789 . ? O6 H6B 0.8503 . ? O9 H9A 0.8476 . ? O9 H9B 0.8504 . ? O12 C20 1.262(10) . ? O13 C32 1.238(10) . ? O13 Nd1 2.339(6) 5 ? O15 C32 1.236(10) . ? O15 Nd1 2.421(6) 6_556 ? O21 H21A 0.8499 . ? O21 H21B 0.8517 . ? O28 H28A 0.8647 . ? O28 H28B 0.8632 . ? C1 C31 1.376(11) . ? C1 C11 1.397(11) . ? C1 H1 0.9300 . ? C10 C19 1.382(10) . ? C10 C18 1.400(11) . ? C10 H10 0.9300 . ? C11 C23 1.371(11) . ? C11 C18 1.479(10) . ? C14 C27 1.370(10) . ? C14 C18 1.399(10) . ? C14 H14 0.9300 . ? C16 C31 1.517(11) . ? C17 C30 1.381(12) . ? C17 C23 1.382(12) . ? C17 H17 0.9300 . ? C19 C25 1.393(10) . ? C19 C20 1.513(10) . ? C23 H23 0.9300 . ? C25 C27 1.384(10) . ? C25 H25 0.9300 . ? C27 C32 1.523(10) . ? C30 C31 1.388(12) . ? C30 H30 0.9300 . ? O26 H26A 0.8526 . ? O26 H26B 0.8520 . ? O1 H1A 0.8503 . ? O1 H1B 0.8500 . ? O7 O7 1.58(6) 7_565 ? 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 O13 Nd1 O15 96.9(2) 5 6 ? O13 Nd1 O28 67.8(3) 5 . ? O15 Nd1 O28 74.6(2) 6 . ? O13 Nd1 O9 74.3(2) 5 . ? O15 Nd1 O9 73.9(2) 6 . ? O28 Nd1 O9 126.3(3) . . ? O13 Nd1 O6 78.0(2) 5 . ? O15 Nd1 O6 143.3(2) 6 . ? O28 Nd1 O6 132.7(2) . . ? O9 Nd1 O6 69.8(2) . . ? O13 Nd1 O3 82.6(2) 5 . ? O15 Nd1 O3 147.8(2) 6 . ? O28 Nd1 O3 75.6(2) . . ? O9 Nd1 O3 135.3(2) . . ? O6 Nd1 O3 68.3(2) . . ? O13 Nd1 O21 143.8(2) 5 . ? O15 Nd1 O21 74.4(2) 6 . ? O28 Nd1 O21 137.9(3) . . ? O9 Nd1 O21 69.5(2) . . ? O6 Nd1 O21 88.3(2) . . ? O3 Nd1 O21 123.33(19) . . ? O13 Nd1 O12 131.7(2) 5 . ? O15 Nd1 O12 128.9(2) 6 . ? O28 Nd1 O12 106.4(3) . . ? O9 Nd1 O12 127.3(2) . . ? O6 Nd1 O12 73.2(2) . . ? O3 Nd1 O12 51.07(18) . . ? O21 Nd1 O12 73.2(2) . . ? O13 Nd1 O26 133.5(3) 5 . ? O15 Nd1 O26 70.2(2) 6 . ? O28 Nd1 O26 65.7(3) . . ? O9 Nd1 O26 136.3(2) . . ? O6 Nd1 O26 137.9(2) . . ? O3 Nd1 O26 86.8(2) . . ? O21 Nd1 O26 77.4(3) . . ? O12 Nd1 O26 64.8(2) . . ? O13 Nd1 C20 106.8(2) 5 . ? O15 Nd1 C20 146.3(2) 6 . ? O28 Nd1 C20 92.4(3) . . ? O9 Nd1 C20 135.1(2) . . ? O6 Nd1 C20 66.9(2) . . ? O3 Nd1 C20 25.6(2) . . ? O21 Nd1 C20 98.0(2) . . ? O12 Nd1 C20 25.6(2) . . ? O26 Nd1 C20 76.1(2) . . ? C20 O3 Nd1 95.2(5) . . ? Nd1 O6 H6A 110.6 . . ? Nd1 O6 H6B 125.9 . . ? H6A O6 H6B 107.0 . . ? Nd1 O9 H9A 143.0 . . ? Nd1 O9 H9B 106.1 . . ? H9A O9 H9B 110.0 . . ? C20 O12 Nd1 92.6(5) . . ? C32 O13 Nd1 160.2(6) . 5 ? C32 O15 Nd1 151.6(6) . 6_556 ? Nd1 O21 H21A 109.5 . . ? Nd1 O21 H21B 110.5 . . ? H21A O21 H21B 109.4 . . ? Nd1 O28 H28A 110.4 . . ? Nd1 O28 H28B 109.9 . . ? H28A O28 H28B 108.7 . . ? C31 C1 C11 121.2(8) . . ? C31 C1 H1 119.4 . . ? C11 C1 H1 119.4 . . ? C19 C10 C18 121.5(7) . . ? C19 C10 H10 119.3 . . ? C18 C10 H10 119.3 . . ? C23 C11 C1 118.3(7) . . ? C23 C11 C18 120.9(7) . . ? C1 C11 C18 120.8(7) . . ? C27 C14 C18 120.9(7) . . ? C27 C14 H14 119.6 . . ? C18 C14 H14 119.6 . . ? O5 C16 O4 123.0(8) . . ? O5 C16 C31 119.2(8) . . ? O4 C16 C31 117.7(8) . . ? C30 C17 C23 119.8(8) . . ? C30 C17 H17 120.1 . . ? C23 C17 H17 120.1 . . ? C14 C18 C10 117.8(7) . . ? C14 C18 C11 120.6(7) . . ? C10 C18 C11 121.6(7) . . ? C10 C19 C25 119.5(7) . . ? C10 C19 C20 120.6(7) . . ? C25 C19 C20 119.9(7) . . ? O12 C20 O3 120.6(7) . . ? O12 C20 C19 120.1(7) . . ? O3 C20 C19 119.3(7) . . ? O12 C20 Nd1 61.8(4) . . ? O3 C20 Nd1 59.2(4) . . ? C19 C20 Nd1 174.3(5) . . ? C11 C23 C17 121.3(8) . . ? C11 C23 H23 119.3 . . ? C17 C23 H23 119.3 . . ? C27 C25 C19 119.5(7) . . ? C27 C25 H25 120.2 . . ? C19 C25 H25 120.2 . . ? C14 C27 C25 120.9(7) . . ? C14 C27 C32 120.5(7) . . ? C25 C27 C32 118.7(7) . . ? C17 C30 C31 119.9(7) . . ? C17 C30 H30 120.1 . . ? C31 C30 H30 120.1 . . ? C1 C31 C30 119.4(7) . . ? C1 C31 C16 120.1(8) . . ? C30 C31 C16 120.5(7) . . ? O15 C32 O13 123.8(8) . . ? O15 C32 C27 118.6(7) . . ? O13 C32 C27 117.7(7) . . ? Nd1 O26 H26A 109.5 . . ? Nd1 O26 H26B 109.2 . . ? H26A O26 H26B 109.4 . . ? H1A O1 H1B 109.5 . . ? 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 O13 Nd1 O3 C20 -161.5(5) 5 . . . ? O15 Nd1 O3 C20 107.4(6) 6 . . . ? O28 Nd1 O3 C20 129.6(6) . . . . ? O9 Nd1 O3 C20 -102.9(5) . . . . ? O6 Nd1 O3 C20 -81.5(5) . . . . ? O21 Nd1 O3 C20 -8.9(6) . . . . ? O12 Nd1 O3 C20 4.0(5) . . . . ? O26 Nd1 O3 C20 63.8(5) . . . . ? O13 Nd1 O12 C20 15.4(6) 5 . . . ? O15 Nd1 O12 C20 -142.3(5) 6 . . . ? O28 Nd1 O12 C20 -59.2(5) . . . . ? O9 Nd1 O12 C20 118.2(5) . . . . ? O6 Nd1 O12 C20 71.4(5) . . . . ? O3 Nd1 O12 C20 -4.0(5) . . . . ? O21 Nd1 O12 C20 164.8(6) . . . . ? O26 Nd1 O12 C20 -111.5(6) . . . . ? C31 C1 C11 C23 2.4(13) . . . . ? C31 C1 C11 C18 -178.8(8) . . . . ? C27 C14 C18 C10 -0.7(12) . . . . ? C27 C14 C18 C11 179.9(8) . . . . ? C19 C10 C18 C14 -0.8(12) . . . . ? C19 C10 C18 C11 178.6(8) . . . . ? C23 C11 C18 C14 -40.6(12) . . . . ? C1 C11 C18 C14 140.6(8) . . . . ? C23 C11 C18 C10 140.0(8) . . . . ? C1 C11 C18 C10 -38.8(12) . . . . ? C18 C10 C19 C25 0.6(12) . . . . ? C18 C10 C19 C20 178.2(7) . . . . ? Nd1 O12 C20 O3 7.2(8) . . . . ? Nd1 O12 C20 C19 -173.9(7) . . . . ? Nd1 O3 C20 O12 -7.4(9) . . . . ? Nd1 O3 C20 C19 173.7(6) . . . . ? C10 C19 C20 O12 -13.3(12) . . . . ? C25 C19 C20 O12 164.3(8) . . . . ? C10 C19 C20 O3 165.6(8) . . . . ? C25 C19 C20 O3 -16.8(12) . . . . ? C10 C19 C20 Nd1 -121(6) . . . . ? C25 C19 C20 Nd1 56(6) . . . . ? O13 Nd1 C20 O12 -168.1(5) 5 . . . ? O15 Nd1 C20 O12 59.2(7) 6 . . . ? O28 Nd1 C20 O12 124.4(5) . . . . ? O9 Nd1 C20 O12 -83.7(6) . . . . ? O6 Nd1 C20 O12 -99.4(5) . . . . ? O3 Nd1 C20 O12 172.8(8) . . . . ? O21 Nd1 C20 O12 -14.7(5) . . . . ? O26 Nd1 C20 O12 60.2(5) . . . . ? O13 Nd1 C20 O3 19.2(6) 5 . . . ? O15 Nd1 C20 O3 -113.6(6) 6 . . . ? O28 Nd1 C20 O3 -48.3(5) . . . . ? O9 Nd1 C20 O3 103.6(5) . . . . ? O6 Nd1 C20 O3 87.8(5) . . . . ? O21 Nd1 C20 O3 172.5(5) . . . . ? O12 Nd1 C20 O3 -172.8(8) . . . . ? O26 Nd1 C20 O3 -112.6(5) . . . . ? O13 Nd1 C20 C19 -57(6) 5 . . . ? O15 Nd1 C20 C19 170(6) 6 . . . ? O28 Nd1 C20 C19 -125(6) . . . . ? O9 Nd1 C20 C19 27(6) . . . . ? O6 Nd1 C20 C19 11(6) . . . . ? O3 Nd1 C20 C19 -76(6) . . . . ? O21 Nd1 C20 C19 96(6) . . . . ? O12 Nd1 C20 C19 111(6) . . . . ? O26 Nd1 C20 C19 171(6) . . . . ? C1 C11 C23 C17 -1.0(14) . . . . ? C18 C11 C23 C17 -179.8(9) . . . . ? C30 C17 C23 C11 -0.2(15) . . . . ? C10 C19 C25 C27 1.0(12) . . . . ? C20 C19 C25 C27 -176.6(7) . . . . ? C18 C14 C27 C25 2.4(13) . . . . ? C18 C14 C27 C32 -177.9(7) . . . . ? C19 C25 C27 C14 -2.5(12) . . . . ? C19 C25 C27 C32 177.8(7) . . . . ? C23 C17 C30 C31 0.0(15) . . . . ? C11 C1 C31 C30 -2.6(13) . . . . ? C11 C1 C31 C16 177.3(7) . . . . ? C17 C30 C31 C1 1.4(13) . . . . ? C17 C30 C31 C16 -178.5(8) . . . . ? O5 C16 C31 C1 -170.4(8) . . . . ? O4 C16 C31 C1 9.5(12) . . . . ? O5 C16 C31 C30 9.5(12) . . . . ? O4 C16 C31 C30 -170.6(8) . . . . ? Nd1 O15 C32 O13 -46.0(17) 6_556 . . . ? Nd1 O15 C32 C27 133.3(10) 6_556 . . . ? Nd1 O13 C32 O15 2(3) 5 . . . ? Nd1 O13 C32 C27 -176.9(15) 5 . . . ? C14 C27 C32 O15 1.4(12) . . . . ? C25 C27 C32 O15 -178.8(8) . . . . ? C14 C27 C32 O13 -179.2(8) . . . . ? C25 C27 C32 O13 0.6(12) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 3.474 _refine_diff_density_min -2.003 _refine_diff_density_rms 0.202 _database_code_depnum_ccdc_archive 'CCDC 918539' ####################################################################### # # 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_512 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H42 O27 Pr2' _chemical_formula_weight 1116.46 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.185(5) _cell_length_b 7.5951(15) _cell_length_c 21.260(4) _cell_angle_alpha 90.00 _cell_angle_beta 114.93(3) _cell_angle_gamma 90.00 _cell_volume 3980.6(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3494 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 25.01 _exptl_crystal_description Prism _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.863 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2224 _exptl_absorpt_coefficient_mu 2.517 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5189 _exptl_absorpt_correction_T_max 0.6329 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 15482 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_unetI/netI 0.0341 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3484 _reflns_number_gt 3210 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0368P)^2^+12.0238P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3484 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0779 _refine_ls_wR_factor_gt 0.0763 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _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 Pr1 Pr 0.574824(8) 0.69857(3) -0.118206(10) 0.01516(9) Uani 1 1 d . . . O1 O 0.64848(11) 0.6511(4) 0.00787(15) 0.0268(7) Uani 1 1 d . . . O2 O 0.57074(11) 0.5146(4) -0.02170(15) 0.0281(7) Uani 1 1 d . . . O3 O 0.52101(12) 0.3282(5) 0.16696(17) 0.0362(9) Uani 1 1 d . . . O4 O 0.58368(13) 0.2869(5) 0.27331(16) 0.0315(8) Uani 1 1 d . . . O5 O 0.88511(13) 0.3014(5) 0.19941(18) 0.0353(8) Uani 1 1 d . . . O6 O 0.94769(12) 0.3030(5) 0.30883(18) 0.0366(8) Uani 1 1 d . . . O7 O 0.65613(13) 0.4942(5) -0.10912(18) 0.0415(8) Uani 1 1 d . . . H7B H 0.6425 0.4228 -0.1429 0.062 Uiso 1 1 d R . . H7A H 0.6762 0.4374 -0.0727 0.062 Uiso 1 1 d R . . O8 O 0.65093(13) 0.9205(5) -0.09940(17) 0.0409(9) Uani 1 1 d . . . H8B H 0.6423 0.9891 -0.1340 0.061 Uiso 1 1 d R . . H8A H 0.6848 0.9200 -0.0760 0.061 Uiso 1 1 d R . . O9 O 0.54887(13) 0.8836(5) -0.03774(16) 0.0339(8) Uani 1 1 d . . . H9A H 0.5379 0.9892 -0.0413 0.051 Uiso 1 1 d R . . H9B H 0.5320 0.8280 -0.0184 0.051 Uiso 1 1 d R . . O10 O 0.54366(15) 0.4035(5) -0.1717(2) 0.0501(10) Uani 1 1 d . . . H10A H 0.5667 0.3273 -0.1712 0.075 Uiso 1 1 d R . . H10B H 0.5101 0.3782 -0.1893 0.075 Uiso 1 1 d R . . O11 O 0.53662(13) 0.9900(5) -0.17272(18) 0.0390(8) Uani 1 1 d . . . H11A H 0.5513 1.0464 -0.1949 0.058 Uiso 1 1 d R . . H11B H 0.5090 1.0322 -0.1690 0.058 Uiso 1 1 d R . . C1 C 0.89982(17) 0.3286(6) 0.2641(2) 0.0236(10) Uani 1 1 d . . . C2 C 0.85806(15) 0.3943(6) 0.2872(2) 0.0200(9) Uani 1 1 d . . . C3 C 0.87301(16) 0.4496(6) 0.3549(2) 0.0268(10) Uani 1 1 d . . . H3 H 0.9094 0.4482 0.3862 0.032 Uiso 1 1 calc R . . C4 C 0.83446(17) 0.5064(7) 0.3762(2) 0.0310(10) Uani 1 1 d . . . H4 H 0.8448 0.5451 0.4215 0.037 Uiso 1 1 calc R . . C5 C 0.77983(17) 0.5060(6) 0.3297(2) 0.0261(10) Uani 1 1 d . . . H5 H 0.7539 0.5437 0.3445 0.031 Uiso 1 1 calc R . . C6 C 0.76368(15) 0.4501(5) 0.2619(2) 0.0184(9) Uani 1 1 d . . . C7 C 0.80382(15) 0.3956(6) 0.2413(2) 0.0201(9) Uani 1 1 d . . . H7 H 0.7938 0.3595 0.1958 0.024 Uiso 1 1 calc R . . C8 C 0.70540(15) 0.4464(5) 0.2123(2) 0.0178(8) Uani 1 1 d . . . C9 C 0.68878(15) 0.5008(6) 0.1439(2) 0.0206(9) Uani 1 1 d . . . H9 H 0.7145 0.5420 0.1292 0.025 Uiso 1 1 calc R . . C10 C 0.63441(15) 0.4945(5) 0.0969(2) 0.0178(8) Uani 1 1 d . . . C11 C 0.61725(16) 0.5563(5) 0.0235(2) 0.0205(9) Uani 1 1 d . . . C12 C 0.59571(15) 0.4368(5) 0.1185(2) 0.0183(8) Uani 1 1 d . . . H12 H 0.5594 0.4320 0.0872 0.022 Uiso 1 1 calc R . . C13 C 0.61117(15) 0.3861(5) 0.1873(2) 0.0166(8) Uani 1 1 d . . . C14 C 0.66579(15) 0.3899(6) 0.2336(2) 0.0179(8) Uani 1 1 d . . . H14 H 0.6761 0.3544 0.2793 0.021 Uiso 1 1 calc R . . C15 C 0.56865(15) 0.3297(5) 0.2108(2) 0.0182(9) Uani 1 1 d . . . O12 O 0.49528(13) 0.7786(4) 0.04636(18) 0.0331(8) Uani 1 1 d . . . H12A H 0.5155 0.7664 0.0895 0.050 Uiso 1 1 d R . . H12B H 0.4722 0.6962 0.0327 0.050 Uiso 1 1 d R . . O13 O 0.6969(5) 0.2285(12) 0.9979(5) 0.077(3) Uani 0.50 1 d P . . O14 O 0.7533(2) 0.7700(8) 0.0631(3) 0.103(2) Uani 1 1 d . . . H14B H 0.7211 0.7926 0.0327 0.154 Uiso 1 1 d R . . H14A H 0.7808 0.8383 0.0809 0.154 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pr1 0.01274(14) 0.02129(14) 0.01220(14) 0.00121(9) 0.00598(10) -0.00113(9) O1 0.0223(15) 0.038(2) 0.0203(16) 0.0083(13) 0.0093(13) -0.0054(13) O2 0.0249(16) 0.0354(19) 0.0183(15) 0.0071(14) 0.0034(13) -0.0075(14) O3 0.0140(16) 0.065(3) 0.0271(18) 0.0043(16) 0.0064(14) -0.0085(15) O4 0.0302(18) 0.051(2) 0.0210(17) 0.0042(15) 0.0184(14) -0.0038(15) O5 0.0307(18) 0.049(2) 0.031(2) -0.0030(16) 0.0183(16) 0.0056(15) O6 0.0169(16) 0.055(2) 0.039(2) 0.0035(16) 0.0122(15) 0.0057(15) O7 0.0393(19) 0.045(2) 0.036(2) -0.0021(17) 0.0115(16) 0.0096(17) O8 0.0296(17) 0.048(2) 0.036(2) 0.0111(17) 0.0049(15) -0.0142(16) O9 0.048(2) 0.0311(18) 0.0329(19) -0.0016(15) 0.0276(16) 0.0054(16) O10 0.048(2) 0.037(2) 0.081(3) -0.024(2) 0.043(2) -0.0108(18) O11 0.0446(19) 0.036(2) 0.053(2) 0.0209(18) 0.0372(18) 0.0165(16) C1 0.021(2) 0.022(2) 0.031(3) 0.0020(18) 0.015(2) -0.0026(18) C2 0.018(2) 0.018(2) 0.025(2) 0.0021(18) 0.0107(17) -0.0001(17) C3 0.014(2) 0.034(3) 0.025(2) 0.0013(19) 0.0023(18) 0.0047(18) C4 0.027(2) 0.045(3) 0.018(2) -0.006(2) 0.0063(19) 0.000(2) C5 0.024(2) 0.037(3) 0.020(2) 0.002(2) 0.0122(18) 0.006(2) C6 0.0128(18) 0.023(2) 0.019(2) 0.0054(17) 0.0063(16) 0.0008(16) C7 0.021(2) 0.022(2) 0.020(2) 0.0007(18) 0.0109(17) -0.0014(18) C8 0.0124(18) 0.023(2) 0.018(2) -0.0001(16) 0.0070(16) 0.0026(16) C9 0.0160(19) 0.025(2) 0.024(2) 0.0036(18) 0.0114(17) 0.0025(17) C10 0.019(2) 0.018(2) 0.019(2) 0.0034(17) 0.0100(17) 0.0033(17) C11 0.022(2) 0.022(2) 0.018(2) 0.0034(17) 0.0088(18) 0.0043(18) C12 0.0136(18) 0.021(2) 0.018(2) 0.0005(16) 0.0051(16) 0.0008(16) C13 0.0181(19) 0.017(2) 0.019(2) -0.0009(17) 0.0117(16) -0.0005(17) C14 0.0172(19) 0.023(2) 0.0141(19) 0.0036(17) 0.0077(16) 0.0030(17) C15 0.015(2) 0.022(2) 0.020(2) -0.0026(17) 0.0099(18) -0.0003(16) O12 0.0358(19) 0.0285(18) 0.036(2) -0.0018(15) 0.0160(16) -0.0072(15) O13 0.143(10) 0.044(5) 0.050(6) 0.007(4) 0.047(6) 0.011(6) O14 0.051(3) 0.138(5) 0.121(5) -0.040(4) 0.038(3) -0.029(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 Pr1 O3 2.372(3) 5_665 ? Pr1 O4 2.420(3) 6_565 ? Pr1 O10 2.494(4) . ? Pr1 O11 2.511(3) . ? Pr1 O2 2.523(3) . ? Pr1 O9 2.533(3) . ? Pr1 O8 2.566(3) . ? Pr1 O1 2.608(3) . ? Pr1 O7 2.641(3) . ? Pr1 C11 2.941(4) . ? O1 C11 1.260(5) . ? O2 C11 1.265(5) . ? O3 C15 1.236(5) . ? O3 Pr1 2.372(3) 5_665 ? O4 C15 1.257(5) . ? O4 Pr1 2.420(3) 6_566 ? O5 C1 1.277(6) . ? O6 C1 1.262(5) . ? O7 H7B 0.8506 . ? O7 H7A 0.8523 . ? O8 H8B 0.8498 . ? O8 H8A 0.8426 . ? O9 H9A 0.8485 . ? O9 H9B 0.8476 . ? O10 H10A 0.8500 . ? O10 H10B 0.8500 . ? O11 H11A 0.8498 . ? O11 H11B 0.8497 . ? C1 C2 1.500(5) . ? C2 C7 1.383(5) . ? C2 C3 1.386(6) . ? C3 C4 1.374(6) . ? C3 H3 0.9300 . ? C4 C5 1.394(6) . ? C4 H4 0.9300 . ? C5 C6 1.386(6) . ? C5 H5 0.9300 . ? C6 C7 1.398(5) . ? C6 C8 1.488(5) . ? C7 H7 0.9300 . ? C8 C9 1.392(5) . ? C8 C14 1.400(5) . ? C9 C10 1.393(5) . ? C9 H9 0.9300 . ? C10 C12 1.385(5) . ? C10 C11 1.502(5) . ? C12 C13 1.395(5) . ? C12 H12 0.9300 . ? C13 C14 1.394(5) . ? C13 C15 1.502(5) . ? C14 H14 0.9300 . ? O12 H12A 0.8523 . ? O12 H12B 0.8466 . ? O14 H14B 0.8587 . ? O14 H14A 0.8565 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Pr1 O4 96.87(11) 5_665 6_565 ? O3 Pr1 O10 67.93(12) 5_665 . ? O4 Pr1 O10 75.99(12) 6_565 . ? O3 Pr1 O11 73.11(12) 5_665 . ? O4 Pr1 O11 73.01(11) 6_565 . ? O10 Pr1 O11 125.92(14) . . ? O3 Pr1 O2 83.75(10) 5_665 . ? O4 Pr1 O2 148.91(11) 6_565 . ? O10 Pr1 O2 75.53(12) . . ? O11 Pr1 O2 135.40(10) . . ? O3 Pr1 O9 77.02(12) 5_665 . ? O4 Pr1 O9 141.82(11) 6_565 . ? O10 Pr1 O9 131.95(11) . . ? O11 Pr1 O9 69.14(11) . . ? O2 Pr1 O9 68.77(11) . . ? O3 Pr1 O8 142.13(12) 5_665 . ? O4 Pr1 O8 73.79(11) 6_565 . ? O10 Pr1 O8 139.28(11) . . ? O11 Pr1 O8 69.05(11) . . ? O2 Pr1 O8 123.09(10) . . ? O9 Pr1 O8 88.06(11) . . ? O3 Pr1 O1 131.55(10) 5_665 . ? O4 Pr1 O1 130.11(10) 6_565 . ? O10 Pr1 O1 108.08(12) . . ? O11 Pr1 O1 125.83(11) . . ? O2 Pr1 O1 50.61(9) . . ? O9 Pr1 O1 72.20(10) . . ? O8 Pr1 O1 73.22(10) . . ? O3 Pr1 O7 135.47(12) 5_665 . ? O4 Pr1 O7 71.35(11) 6_565 . ? O10 Pr1 O7 67.55(12) . . ? O11 Pr1 O7 136.26(11) . . ? O2 Pr1 O7 86.41(11) . . ? O9 Pr1 O7 137.69(11) . . ? O8 Pr1 O7 77.27(12) . . ? O1 Pr1 O7 65.61(10) . . ? O3 Pr1 C11 107.48(11) 5_665 . ? O4 Pr1 C11 147.11(11) 6_565 . ? O10 Pr1 C11 92.76(13) . . ? O11 Pr1 C11 134.75(11) . . ? O2 Pr1 C11 25.31(10) . . ? O9 Pr1 C11 67.19(11) . . ? O8 Pr1 C11 98.02(11) . . ? O1 Pr1 C11 25.35(10) . . ? O7 Pr1 C11 75.79(11) . . ? C11 O1 Pr1 92.3(2) . . ? C11 O2 Pr1 96.1(2) . . ? C15 O3 Pr1 159.8(3) . 5_665 ? C15 O4 Pr1 151.2(3) . 6_566 ? Pr1 O7 H7B 105.0 . . ? Pr1 O7 H7A 123.9 . . ? H7B O7 H7A 109.2 . . ? Pr1 O8 H8B 111.0 . . ? Pr1 O8 H8A 134.3 . . ? H8B O8 H8A 110.3 . . ? Pr1 O9 H9A 130.8 . . ? Pr1 O9 H9B 114.5 . . ? H9A O9 H9B 105.7 . . ? Pr1 O10 H10A 120.0 . . ? Pr1 O10 H10B 120.0 . . ? H10A O10 H10B 120.0 . . ? Pr1 O11 H11A 120.0 . . ? Pr1 O11 H11B 120.0 . . ? H11A O11 H11B 120.0 . . ? O6 C1 O5 122.8(4) . . ? O6 C1 C2 119.1(4) . . ? O5 C1 C2 118.1(4) . . ? C7 C2 C3 119.3(4) . . ? C7 C2 C1 120.0(4) . . ? C3 C2 C1 120.7(4) . . ? C4 C3 C2 120.4(4) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.0(4) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.9(4) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 118.0(4) . . ? C5 C6 C8 121.2(3) . . ? C7 C6 C8 120.8(4) . . ? C2 C7 C6 121.5(4) . . ? C2 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C9 C8 C14 118.3(3) . . ? C9 C8 C6 120.9(3) . . ? C14 C8 C6 120.8(3) . . ? C8 C9 C10 121.2(3) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C12 C10 C9 119.9(4) . . ? C12 C10 C11 119.8(3) . . ? C9 C10 C11 120.3(3) . . ? O1 C11 O2 120.7(4) . . ? O1 C11 C10 120.3(4) . . ? O2 C11 C10 119.0(3) . . ? O1 C11 Pr1 62.4(2) . . ? O2 C11 Pr1 58.5(2) . . ? C10 C11 Pr1 174.1(3) . . ? C10 C12 C13 120.0(3) . . ? C10 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 119.7(3) . . ? C14 C13 C15 120.7(3) . . ? C12 C13 C15 119.6(3) . . ? C13 C14 C8 120.9(4) . . ? C13 C14 H14 119.6 . . ? C8 C14 H14 119.6 . . ? O3 C15 O4 124.4(4) . . ? O3 C15 C13 117.4(4) . . ? O4 C15 C13 118.2(3) . . ? H12A O12 H12B 109.7 . . ? H14B O14 H14A 129.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Pr1 O1 C11 21.0(3) 5_665 . . . ? O4 Pr1 O1 C11 -141.9(2) 6_565 . . . ? O10 Pr1 O1 C11 -55.2(3) . . . . ? O11 Pr1 O1 C11 120.3(2) . . . . ? O2 Pr1 O1 C11 -2.7(2) . . . . ? O9 Pr1 O1 C11 74.1(2) . . . . ? O8 Pr1 O1 C11 167.6(3) . . . . ? O7 Pr1 O1 C11 -109.1(3) . . . . ? O3 Pr1 O2 C11 -159.8(3) 5_665 . . . ? O4 Pr1 O2 C11 107.3(3) 6_565 . . . ? O10 Pr1 O2 C11 131.5(3) . . . . ? O11 Pr1 O2 C11 -101.6(3) . . . . ? O9 Pr1 O2 C11 -81.3(3) . . . . ? O8 Pr1 O2 C11 -8.5(3) . . . . ? O1 Pr1 O2 C11 2.7(2) . . . . ? O7 Pr1 O2 C11 63.7(3) . . . . ? O6 C1 C2 C7 -169.3(4) . . . . ? O5 C1 C2 C7 10.8(6) . . . . ? O6 C1 C2 C3 9.0(6) . . . . ? O5 C1 C2 C3 -170.9(4) . . . . ? C7 C2 C3 C4 -0.5(7) . . . . ? C1 C2 C3 C4 -178.8(4) . . . . ? C2 C3 C4 C5 1.0(7) . . . . ? C3 C4 C5 C6 -0.5(8) . . . . ? C4 C5 C6 C7 -0.5(7) . . . . ? C4 C5 C6 C8 179.0(4) . . . . ? C3 C2 C7 C6 -0.6(6) . . . . ? C1 C2 C7 C6 177.7(4) . . . . ? C5 C6 C7 C2 1.1(6) . . . . ? C8 C6 C7 C2 -178.4(4) . . . . ? C5 C6 C8 C9 138.8(4) . . . . ? C7 C6 C8 C9 -41.7(6) . . . . ? C5 C6 C8 C14 -40.5(6) . . . . ? C7 C6 C8 C14 138.9(4) . . . . ? C14 C8 C9 C10 -1.9(6) . . . . ? C6 C8 C9 C10 178.7(4) . . . . ? C8 C9 C10 C12 1.4(6) . . . . ? C8 C9 C10 C11 179.1(4) . . . . ? Pr1 O1 C11 O2 4.8(4) . . . . ? Pr1 O1 C11 C10 -173.9(3) . . . . ? Pr1 O2 C11 O1 -4.9(4) . . . . ? Pr1 O2 C11 C10 173.8(3) . . . . ? C12 C10 C11 O1 161.0(4) . . . . ? C9 C10 C11 O1 -16.7(6) . . . . ? C12 C10 C11 O2 -17.7(6) . . . . ? C9 C10 C11 O2 164.6(4) . . . . ? C12 C10 C11 Pr1 46(3) . . . . ? C9 C10 C11 Pr1 -132(3) . . . . ? O3 Pr1 C11 O1 -163.7(2) 5_665 . . . ? O4 Pr1 C11 O1 60.4(3) 6_565 . . . ? O10 Pr1 C11 O1 128.6(2) . . . . ? O11 Pr1 C11 O1 -80.4(3) . . . . ? O2 Pr1 C11 O1 175.2(4) . . . . ? O9 Pr1 C11 O1 -96.5(3) . . . . ? O8 Pr1 C11 O1 -12.0(3) . . . . ? O7 Pr1 C11 O1 62.6(2) . . . . ? O3 Pr1 C11 O2 21.1(3) 5_665 . . . ? O4 Pr1 C11 O2 -114.8(3) 6_565 . . . ? O10 Pr1 C11 O2 -46.6(3) . . . . ? O11 Pr1 C11 O2 104.4(3) . . . . ? O9 Pr1 C11 O2 88.3(3) . . . . ? O8 Pr1 C11 O2 172.8(2) . . . . ? O1 Pr1 C11 O2 -175.2(4) . . . . ? O7 Pr1 C11 O2 -112.6(3) . . . . ? O3 Pr1 C11 C10 -46(3) 5_665 . . . ? O4 Pr1 C11 C10 178(3) 6_565 . . . ? O10 Pr1 C11 C10 -114(3) . . . . ? O11 Pr1 C11 C10 37(3) . . . . ? O2 Pr1 C11 C10 -67(3) . . . . ? O9 Pr1 C11 C10 21(3) . . . . ? O8 Pr1 C11 C10 106(3) . . . . ? O1 Pr1 C11 C10 118(3) . . . . ? O7 Pr1 C11 C10 -180(100) . . . . ? C9 C10 C12 C13 0.3(6) . . . . ? C11 C10 C12 C13 -177.4(4) . . . . ? C10 C12 C13 C14 -1.5(6) . . . . ? C10 C12 C13 C15 177.9(4) . . . . ? C12 C13 C14 C8 0.9(6) . . . . ? C15 C13 C14 C8 -178.4(4) . . . . ? C9 C8 C14 C13 0.8(6) . . . . ? C6 C8 C14 C13 -179.9(4) . . . . ? Pr1 O3 C15 O4 5.8(12) 5_665 . . . ? Pr1 O3 C15 C13 -174.4(7) 5_665 . . . ? Pr1 O4 C15 O3 -47.2(9) 6_566 . . . ? Pr1 O4 C15 C13 133.0(5) 6_566 . . . ? C14 C13 C15 O3 -179.5(4) . . . . ? C12 C13 C15 O3 1.1(6) . . . . ? C14 C13 C15 O4 0.3(6) . . . . ? C12 C13 C15 O4 -179.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.589 _refine_diff_density_min -1.051 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 918540' ####################################################################### # # 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_601h _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H36 O23 Sm2' _chemical_formula_weight 1065.29 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 27.284(5) _cell_length_b 7.4955(15) _cell_length_c 20.849(4) _cell_angle_alpha 90.00 _cell_angle_beta 115.02(3) _cell_angle_gamma 90.00 _cell_volume 3863.7(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4582 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 27.84 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.831 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 3.097 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.3705 _exptl_absorpt_correction_T_max 0.5763 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19213 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 27.84 _reflns_number_total 4582 _reflns_number_gt 3793 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.we are use 172 restraints as foll DFIX 1.35 0.001 H9A H9B DFIX 0.85 0.001 H9A O9 DFIX 1.35 0.001 H12A H12B DFIX 0.85 0.001 H12A O12 H12B O12 DFIX 1.35 0.001 H10A H10B DFIX 0.85 0.001 H10A O10 DFIX 0.85 0.001 H11A O11 H11B O11 DFIX 1.35 0.001 H11A H11B isor 0.01 $c $o SIZE 0.2 0.2 0.4 EXTI 0.00138 ; _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^)+(0.0710P)^2^+20.7562P] 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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00138(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4582 _refine_ls_number_parameters 278 _refine_ls_number_restraints 172 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1247 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.066 _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 Sm1 Sm 0.072496(11) 0.79112(4) 0.381794(14) 0.02685(14) Uani 1 1 d . . . O1 O 0.0827(2) 0.7813(7) 0.2760(3) 0.0441(12) Uani 1 1 d U . . O2 O 0.01984(19) 0.8207(8) 0.1689(3) 0.0493(13) Uani 1 1 d U . . O3 O 0.06584(19) 1.0191(7) -0.0249(2) 0.0405(11) Uani 1 1 d U . . O4 O 0.14550(18) 1.1322(8) 0.0019(3) 0.0522(14) Uani 1 1 d U . . O6 O 0.44382(19) 0.8129(8) 0.3044(3) 0.0500(13) Uani 1 1 d U . . O5 O 0.3812(2) 0.8116(7) 0.1942(3) 0.0458(12) Uani 1 1 d U . . O9 O 0.1501(2) 0.5898(8) 0.4068(3) 0.0537(14) Uani 1 1 d DU . . H9B H 0.1465 0.4785 0.4113 0.064 Uiso 1 1 d RD . . O7 O 0.0451(3) 1.0870(10) 0.3261(4) 0.094(2) Uani 1 1 d U . . H7A H 0.0688 1.1609 0.3264 0.112 Uiso 1 1 d R . . H7B H 0.0117 1.1147 0.3066 0.112 Uiso 1 1 d R . . O8 O 0.0385(2) 0.4980(7) 0.3306(3) 0.0460(12) Uani 1 1 d U . . H8A H 0.0534 0.4424 0.3080 0.055 Uiso 1 1 d R . . H8B H 0.0118 0.4517 0.3354 0.055 Uiso 1 1 d R . . O11 O 0.0493(2) 0.6132(7) 0.4642(3) 0.0431(11) Uani 1 1 d DU . . C8 C 0.0676(2) 0.8227(8) 0.2125(3) 0.0281(12) Uani 1 1 d U . . C5 C 0.1095(2) 0.8795(8) 0.1869(3) 0.0266(11) Uani 1 1 d U . . C4 C 0.0934(2) 0.9282(8) 0.1173(3) 0.0275(12) Uani 1 1 d U . . H4 H 0.0570 0.9242 0.0861 0.033 Uiso 1 1 calc R . . C1 C 0.2028(2) 0.9346(8) 0.2110(3) 0.0278(12) Uani 1 1 d U . . C6 C 0.1638(2) 0.8812(8) 0.2334(3) 0.0263(11) Uani 1 1 d U . . H6 H 0.1742 0.8461 0.2801 0.032 Uiso 1 1 calc R . . C15 C 0.3961(3) 0.8330(9) 0.2594(4) 0.0347(14) Uani 1 1 d U . . C10 C 0.3004(2) 0.8930(8) 0.2388(3) 0.0278(12) Uani 1 1 d U . . H10 H 0.2903 0.8619 0.1917 0.033 Uiso 1 1 calc R . . C2 C 0.1858(2) 0.9887(8) 0.1412(3) 0.0287(12) Uani 1 1 d U . . H2 H 0.2113 1.0295 0.1259 0.034 Uiso 1 1 calc R . . C7 C 0.1135(2) 1.0460(9) 0.0196(3) 0.0306(13) Uani 1 1 d U . . C11 C 0.3545(2) 0.8921(8) 0.2853(3) 0.0293(12) Uani 1 1 d U . . C3 C 0.1314(2) 0.9832(8) 0.0935(3) 0.0277(12) Uani 1 1 d U . . C14 C 0.2768(3) 0.9887(10) 0.3307(3) 0.0375(15) Uani 1 1 d U . . H14 H 0.2509 1.0213 0.3464 0.045 Uiso 1 1 calc R . . C9 C 0.2606(2) 0.9394(8) 0.2607(3) 0.0276(12) Uani 1 1 d U . . C12 C 0.3697(2) 0.9404(9) 0.3549(3) 0.0373(14) Uani 1 1 d U . . H12 H 0.4060 0.9392 0.3865 0.045 Uiso 1 1 calc R . . C13 C 0.3310(3) 0.9904(11) 0.3777(4) 0.0439(16) Uani 1 1 d U . . H13 H 0.3413 1.0251 0.4244 0.053 Uiso 1 1 calc R . . O10 O 0.1513(4) 1.0075(13) 0.3872(5) 0.041(2) Uani 0.50 1 d PDU . . H10B H 0.1453 1.1187 0.3806 0.050 Uiso 0.50 1 d PRD . . O12 O 0.0020(2) 0.2788(7) 0.4493(3) 0.0427(12) Uani 1 1 d DU . . H10A H 0.123(2) 0.9572(13) 0.357(5) 0.17(6) Uiso 1 1 d D . . H11A H 0.045(2) 0.686(8) 0.431(3) 0.17(7) Uiso 1 1 d D . . H11B H 0.036(3) 0.665(8) 0.490(3) 0.034(19) Uiso 1 1 d D . . H12B H 0.0304(14) 0.25(2) 0.444(4) 0.19(9) Uiso 1 1 d D . . H12A H -0.0235(19) 0.276(14) 0.4079(16) 0.09(4) Uiso 1 1 d D . . H9A H 0.146(7) 0.603(3) 0.364(3) 0.21(9) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sm1 0.02463(19) 0.0359(2) 0.02005(19) -0.00306(12) 0.00944(13) 0.00413(13) O1 0.041(3) 0.067(3) 0.034(3) 0.009(2) 0.025(2) 0.001(2) O2 0.026(2) 0.082(4) 0.042(3) -0.003(3) 0.015(2) -0.013(2) O3 0.040(2) 0.047(3) 0.028(2) 0.009(2) 0.0080(19) -0.014(2) O4 0.031(2) 0.081(4) 0.048(3) 0.031(3) 0.020(2) 0.000(2) O6 0.028(2) 0.072(4) 0.052(3) 0.003(3) 0.019(2) 0.005(2) O5 0.045(3) 0.058(3) 0.045(3) 0.000(2) 0.028(2) 0.004(2) O9 0.044(3) 0.051(3) 0.055(3) -0.004(2) 0.010(2) 0.017(2) O7 0.122(5) 0.065(4) 0.134(6) 0.015(4) 0.093(5) 0.007(4) O8 0.051(3) 0.045(3) 0.059(3) -0.012(2) 0.040(3) -0.010(2) O11 0.060(3) 0.048(3) 0.034(2) 0.003(2) 0.032(2) 0.000(2) C8 0.026(3) 0.029(3) 0.033(3) 0.000(2) 0.017(2) -0.001(2) C5 0.027(3) 0.028(3) 0.028(3) 0.003(2) 0.015(2) 0.002(2) C4 0.022(2) 0.034(3) 0.025(3) 0.005(2) 0.007(2) 0.001(2) C1 0.023(3) 0.031(3) 0.032(3) 0.003(2) 0.014(2) 0.002(2) C6 0.027(3) 0.030(3) 0.023(3) 0.005(2) 0.011(2) 0.004(2) C15 0.032(3) 0.033(3) 0.044(4) 0.000(3) 0.021(3) -0.003(2) C10 0.023(3) 0.030(3) 0.029(3) -0.001(2) 0.010(2) -0.001(2) C2 0.025(3) 0.032(3) 0.034(3) 0.006(2) 0.017(2) 0.000(2) C7 0.027(3) 0.036(3) 0.031(3) 0.010(3) 0.014(2) 0.006(2) C11 0.023(3) 0.028(3) 0.037(3) 0.001(2) 0.013(2) -0.004(2) C3 0.023(3) 0.036(3) 0.025(3) 0.006(2) 0.012(2) 0.004(2) C14 0.033(3) 0.050(4) 0.034(3) 0.006(3) 0.018(3) 0.009(3) C9 0.024(3) 0.029(3) 0.029(3) 0.006(2) 0.010(2) 0.003(2) C12 0.025(3) 0.046(4) 0.035(3) 0.003(3) 0.006(2) 0.002(3) C13 0.042(3) 0.055(4) 0.032(3) -0.005(3) 0.012(3) 0.003(3) O10 0.052(5) 0.042(5) 0.035(4) 0.004(4) 0.022(4) -0.012(4) O12 0.046(3) 0.041(3) 0.045(3) 0.001(2) 0.024(3) 0.002(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 Sm1 O2 2.294(5) 2 ? Sm1 O1 2.338(5) . ? Sm1 O8 2.448(5) . ? Sm1 O11 2.458(5) . ? Sm1 O7 2.468(7) . ? Sm1 O9 2.469(5) . ? Sm1 O3 2.477(4) 6_576 ? Sm1 O4 2.520(5) 6_576 ? Sm1 O10 2.658(9) . ? Sm1 C7 2.877(6) 6_576 ? Sm1 H10A 2.09(10) . ? Sm1 H11A 1.70(3) . ? Sm1 H9A 2.60(14) . ? O1 C8 1.248(8) . ? O2 C8 1.234(8) . ? O2 Sm1 2.294(5) 2 ? O3 C7 1.255(7) . ? O3 Sm1 2.477(4) 6_575 ? O4 C7 1.259(7) . ? O4 Sm1 2.520(5) 6_575 ? O6 C15 1.250(8) . ? O5 C15 1.255(8) . ? O9 H9B 0.8499 . ? O9 H9A 0.8500(12) . ? O7 H7A 0.8500 . ? O7 H7B 0.8499 . ? O8 H8A 0.8501 . ? O8 H8B 0.8499 . ? O11 H11A 0.8500(11) . ? O11 H11B 0.8500(10) . ? C8 C5 1.513(7) . ? C5 C4 1.376(8) . ? C5 C6 1.385(8) . ? C4 C3 1.389(7) . ? C4 H4 0.9300 . ? C1 C2 1.387(8) . ? C1 C6 1.390(7) . ? C1 C9 1.478(8) . ? C6 H6 0.9300 . ? C15 C11 1.515(8) . ? C10 C11 1.382(8) . ? C10 C9 1.387(8) . ? C10 H10 0.9300 . ? C2 C3 1.394(8) . ? C2 H2 0.9300 . ? C7 C3 1.482(8) . ? C7 Sm1 2.877(6) 6_575 ? C11 C12 1.378(9) . ? C14 C9 1.384(8) . ? C14 C13 1.386(9) . ? C14 H14 0.9300 . ? C12 C13 1.380(9) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? O10 H10B 0.8500 . ? O10 H10A 0.8500(11) . ? O12 H12B 0.8500(12) . ? O12 H12A 0.8500(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Sm1 O1 96.54(18) 2 . ? O2 Sm1 O8 75.26(19) 2 . ? O1 Sm1 O8 74.63(17) . . ? O2 Sm1 O11 79.51(19) 2 . ? O1 Sm1 O11 144.12(18) . . ? O8 Sm1 O11 69.86(16) . . ? O2 Sm1 O7 68.9(2) 2 . ? O1 Sm1 O7 73.6(2) . . ? O8 Sm1 O7 128.2(3) . . ? O11 Sm1 O7 134.4(2) . . ? O2 Sm1 O9 146.4(2) 2 . ? O1 Sm1 O9 75.3(2) . . ? O8 Sm1 O9 71.13(18) . . ? O11 Sm1 O9 88.4(2) . . ? O7 Sm1 O9 135.3(2) . . ? O2 Sm1 O3 82.85(17) 2 6_576 ? O1 Sm1 O3 146.73(18) . 6_576 ? O8 Sm1 O3 135.86(16) . 6_576 ? O11 Sm1 O3 68.73(18) . 6_576 ? O7 Sm1 O3 75.2(2) . 6_576 ? O9 Sm1 O3 121.75(17) . 6_576 ? O2 Sm1 O4 133.52(16) 2 6_576 ? O1 Sm1 O4 125.80(17) . 6_576 ? O8 Sm1 O4 129.27(19) . 6_576 ? O11 Sm1 O4 76.01(18) . 6_576 ? O7 Sm1 O4 102.5(3) . 6_576 ? O9 Sm1 O4 71.52(18) . 6_576 ? O3 Sm1 O4 51.57(15) 6_576 6_576 ? O2 Sm1 O10 132.2(3) 2 . ? O1 Sm1 O10 69.0(2) . . ? O8 Sm1 O10 135.8(2) . . ? O11 Sm1 O10 138.0(2) . . ? O7 Sm1 O10 63.3(3) . . ? O9 Sm1 O10 76.0(3) . . ? O3 Sm1 O10 86.7(2) 6_576 . ? O4 Sm1 O10 62.2(2) 6_576 . ? O2 Sm1 C7 107.90(18) 2 6_576 ? O1 Sm1 C7 143.50(18) . 6_576 ? O8 Sm1 C7 137.07(18) . 6_576 ? O11 Sm1 C7 68.85(18) . 6_576 ? O7 Sm1 C7 90.0(2) . 6_576 ? O9 Sm1 C7 96.42(19) . 6_576 ? O3 Sm1 C7 25.74(16) 6_576 6_576 ? O4 Sm1 C7 25.91(15) 6_576 6_576 ? O10 Sm1 C7 74.5(2) . 6_576 ? O2 Sm1 H10A 122.8(3) 2 . ? O1 Sm1 H10A 55(2) . . ? O8 Sm1 H10A 127(3) . . ? O11 Sm1 H10A 153.2(16) . . ? O7 Sm1 H10A 56.4(10) . . ? O9 Sm1 H10A 79.5(13) . . ? O3 Sm1 H10A 98(3) 6_576 . ? O4 Sm1 H10A 77.5(18) 6_576 . ? O10 Sm1 H10A 15.4(19) . . ? C7 Sm1 H10A 89(2) 6_576 . ? O2 Sm1 H11A 69.1(17) 2 . ? O1 Sm1 H11A 144(3) . . ? O8 Sm1 H11A 70(3) . . ? O11 Sm1 H11A 10.7(16) . . ? O7 Sm1 H11A 125.2(18) . . ? O9 Sm1 H11A 98.5(17) . . ? O3 Sm1 H11A 66(3) 6_576 . ? O4 Sm1 H11A 83(2) 6_576 . ? O10 Sm1 H11A 144(3) . . ? C7 Sm1 H11A 71(3) 6_576 . ? H10A Sm1 H11A 160(3) . . ? O2 Sm1 H9A 139(2) 2 . ? O1 Sm1 H9A 56.2(10) . . ? O8 Sm1 H9A 68(2) . . ? O11 Sm1 H9A 104.2(3) . . ? O7 Sm1 H9A 121.3(4) . . ? O9 Sm1 H9A 19.1(10) . . ? O3 Sm1 H9A 138(2) 6_576 . ? O4 Sm1 H9A 86(2) 6_576 . ? O10 Sm1 H9A 71.2(17) . . ? C7 Sm1 H9A 112(2) 6_576 . ? H10A Sm1 H9A 70(2) . . ? H11A Sm1 H9A 113.5(19) . . ? C8 O1 Sm1 151.1(4) . . ? C8 O2 Sm1 162.3(4) . 2 ? C7 O3 Sm1 95.2(4) . 6_575 ? C7 O4 Sm1 93.1(4) . 6_575 ? Sm1 O9 H9B 119.8 . . ? Sm1 O9 H9A 89(10) . . ? H9B O9 H9A 105.1 . . ? Sm1 O7 H7A 120.3 . . ? Sm1 O7 H7B 119.7 . . ? H7A O7 H7B 120.0 . . ? Sm1 O8 H8A 120.0 . . ? Sm1 O8 H8B 120.0 . . ? H8A O8 H8B 120.0 . . ? Sm1 O11 H11A 22(4) . . ? Sm1 O11 H11B 119(5) . . ? H11A O11 H11B 105.14(17) . . ? O2 C8 O1 123.4(6) . . ? O2 C8 C5 117.6(5) . . ? O1 C8 C5 119.0(5) . . ? C4 C5 C6 120.3(5) . . ? C4 C5 C8 119.7(5) . . ? C6 C5 C8 119.9(5) . . ? C5 C4 C3 120.2(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C2 C1 C6 118.3(5) . . ? C2 C1 C9 120.8(5) . . ? C6 C1 C9 120.9(5) . . ? C5 C6 C1 120.8(5) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? O6 C15 O5 123.7(6) . . ? O6 C15 C11 117.9(6) . . ? O5 C15 C11 118.4(6) . . ? C11 C10 C9 121.5(5) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C1 C2 C3 121.5(5) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? O3 C7 O4 119.7(5) . . ? O3 C7 C3 120.1(5) . . ? O4 C7 C3 120.2(5) . . ? O3 C7 Sm1 59.0(3) . 6_575 ? O4 C7 Sm1 61.0(3) . 6_575 ? C3 C7 Sm1 172.2(4) . 6_575 ? C12 C11 C10 119.5(5) . . ? C12 C11 C15 121.0(5) . . ? C10 C11 C15 119.5(6) . . ? C4 C3 C2 119.0(5) . . ? C4 C3 C7 119.9(5) . . ? C2 C3 C7 121.0(5) . . ? C9 C14 C13 121.1(6) . . ? C9 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C9 C10 118.0(5) . . ? C14 C9 C1 121.0(5) . . ? C10 C9 C1 121.0(5) . . ? C11 C12 C13 120.1(6) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C14 119.8(6) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? Sm1 O10 H10B 119.6 . . ? Sm1 O10 H10A 41(8) . . ? H10B O10 H10A 105.1 . . ? H12B O12 H12A 105.15(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Sm1 O1 C8 29.4(10) 2 . . . ? O8 Sm1 O1 C8 102.1(10) . . . . ? O11 Sm1 O1 C8 110.5(9) . . . . ? O7 Sm1 O1 C8 -36.4(9) . . . . ? O9 Sm1 O1 C8 176.2(10) . . . . ? O3 Sm1 O1 C8 -57.5(10) 6_576 . . . ? O4 Sm1 O1 C8 -130.2(9) 6_576 . . . ? O10 Sm1 O1 C8 -103.5(10) . . . . ? C7 Sm1 O1 C8 -103.0(9) 6_576 . . . ? Sm1 O2 C8 O1 1(2) 2 . . . ? Sm1 O2 C8 C5 -178.1(13) 2 . . . ? Sm1 O1 C8 O2 -42.6(13) . . . . ? Sm1 O1 C8 C5 137.0(7) . . . . ? O2 C8 C5 C4 0.7(9) . . . . ? O1 C8 C5 C4 -179.0(6) . . . . ? O2 C8 C5 C6 -178.9(6) . . . . ? O1 C8 C5 C6 1.5(9) . . . . ? C6 C5 C4 C3 -1.4(9) . . . . ? C8 C5 C4 C3 179.0(6) . . . . ? C4 C5 C6 C1 1.1(9) . . . . ? C8 C5 C6 C1 -179.4(6) . . . . ? C2 C1 C6 C5 0.9(9) . . . . ? C9 C1 C6 C5 179.0(6) . . . . ? C6 C1 C2 C3 -2.6(9) . . . . ? C9 C1 C2 C3 179.3(6) . . . . ? Sm1 O3 C7 O4 -6.4(7) 6_575 . . . ? Sm1 O3 C7 C3 171.0(5) 6_575 . . . ? Sm1 O4 C7 O3 6.3(7) 6_575 . . . ? Sm1 O4 C7 C3 -171.1(5) 6_575 . . . ? C9 C10 C11 C12 -0.8(9) . . . . ? C9 C10 C11 C15 177.5(6) . . . . ? O6 C15 C11 C12 6.8(9) . . . . ? O5 C15 C11 C12 -171.4(6) . . . . ? O6 C15 C11 C10 -171.5(6) . . . . ? O5 C15 C11 C10 10.3(9) . . . . ? C5 C4 C3 C2 -0.2(9) . . . . ? C5 C4 C3 C7 -176.2(6) . . . . ? C1 C2 C3 C4 2.3(9) . . . . ? C1 C2 C3 C7 178.3(6) . . . . ? O3 C7 C3 C4 -13.2(10) . . . . ? O4 C7 C3 C4 164.2(6) . . . . ? Sm1 C7 C3 C4 68(3) 6_575 . . . ? O3 C7 C3 C2 170.9(6) . . . . ? O4 C7 C3 C2 -11.7(10) . . . . ? Sm1 C7 C3 C2 -108(3) 6_575 . . . ? C13 C14 C9 C10 -0.5(10) . . . . ? C13 C14 C9 C1 178.9(6) . . . . ? C11 C10 C9 C14 1.3(9) . . . . ? C11 C10 C9 C1 -178.1(6) . . . . ? C2 C1 C9 C14 141.9(7) . . . . ? C6 C1 C9 C14 -36.1(9) . . . . ? C2 C1 C9 C10 -38.6(9) . . . . ? C6 C1 C9 C10 143.4(6) . . . . ? C10 C11 C12 C13 -0.4(10) . . . . ? C15 C11 C12 C13 -178.7(6) . . . . ? C11 C12 C13 C14 1.2(11) . . . . ? C9 C14 C13 C12 -0.7(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.84 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.740 _refine_diff_density_min -1.291 _refine_diff_density_rms 0.196 _database_code_depnum_ccdc_archive 'CCDC 918541' ####################################################################### # # 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_shelxl _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 N O11 Tb' _chemical_formula_weight 587.29 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' N N 0.0061 0.0033 '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 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 13.750(3) _cell_length_b 7.6108(15) _cell_length_c 21.492(7) _cell_angle_alpha 90.00 _cell_angle_beta 116.07(2) _cell_angle_gamma 90.00 _cell_volume 2020.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3550 _cell_measurement_theta_min 3.04 _cell_measurement_theta_max 25.01 _exptl_crystal_description 0 _exptl_crystal_colour 0 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.931 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 3.563 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.3298 _exptl_absorpt_correction_T_max 0.5359 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16280 _diffrn_reflns_av_R_equivalents 0.0823 _diffrn_reflns_av_unetI/netI 0.0470 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3550 _reflns_number_gt 3296 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. we are use 9 restraints are as following DFIX 0.85 0.01 H8B O8 O8 H8A DFIX 1.35 0.01 H8B H8A SIZE 0.2 0.2 0.4 DFIX 0.85 0.01 H9B O9 O9 H9B DFIX 1.35 0.01 H9B H9A DFIX 0.85 0.01 H11B O11 O11 H11B DFIX 1.35 0.01 H11B H11A OMIT -3.00 50.02 HTAB ; _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^)+(0.0180P)^2^+4.4470P] 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 NONE _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3550 _refine_ls_number_parameters 297 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0305 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0701 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.068 _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 O10 O 0.4277(3) 0.4956(5) 1.1795(2) 0.0407(9) Uani 1 1 d . . . H10A H 0.4353 0.5885 1.1601 0.049 Uiso 1 1 d R . . Tb1 Tb 0.358954(14) 0.23219(2) 1.112373(9) 0.01728(9) Uani 1 1 d . . . O1 O 0.3816(2) 0.0394(4) 1.02725(14) 0.0245(6) Uani 1 1 d . . . O2 O 0.2144(2) 0.0985(4) 1.00860(15) 0.0317(7) Uani 1 1 d . . . O3 O -0.2706(3) -0.2149(4) 0.81626(17) 0.0353(8) Uani 1 1 d . . . O4 O -0.3967(3) -0.2166(5) 0.70589(19) 0.0382(8) Uani 1 1 d . . . O5 O 0.3223(3) -0.2423(5) 0.73436(19) 0.0475(10) Uani 1 1 d . . . O6 O 0.4572(3) -0.2026(5) 0.83863(18) 0.0416(9) Uani 1 1 d . . . O7 O 0.2146(3) 0.4400(4) 1.06275(18) 0.0411(8) Uani 1 1 d . . . O8 O 0.4019(3) 0.4017(4) 1.03241(18) 0.0385(8) Uani 1 1 d D . . H8A H 0.3841 0.3633 0.9917 0.046 Uiso 1 1 d RD . . O9 O 0.3962(4) -0.0574(4) 1.1624(2) 0.0485(10) Uani 1 1 d D . . N1 N 0.1116(3) 0.6826(6) 1.0489(2) 0.0370(9) Uani 1 1 d . . . C1 C -0.0264(3) -0.0947(5) 0.7533(2) 0.0208(8) Uani 1 1 d . . . C2 C -0.1046(3) -0.1394(5) 0.7754(2) 0.0222(8) Uani 1 1 d . . . H2 H -0.0835 -0.1667 0.8217 0.027 Uiso 1 1 calc R . . C3 C -0.2150(3) -0.1437(5) 0.7284(2) 0.0222(8) Uani 1 1 d . . . C4 C -0.2454(3) -0.1024(6) 0.6596(2) 0.0292(10) Uani 1 1 d . . . H4 H -0.3183 -0.1033 0.6284 0.035 Uiso 1 1 calc R . . C5 C -0.1682(4) -0.0595(6) 0.6366(2) 0.0322(10) Uani 1 1 d . . . H5 H -0.1894 -0.0345 0.5901 0.039 Uiso 1 1 calc R . . C6 C -0.0600(3) -0.0543(6) 0.6833(2) 0.0252(9) Uani 1 1 d . . . H6 H -0.0087 -0.0235 0.6680 0.030 Uiso 1 1 calc R . . C7 C -0.3008(3) -0.1954(6) 0.7514(2) 0.0266(9) Uani 1 1 d . . . C8 C 0.0917(3) -0.0914(5) 0.8023(2) 0.0198(8) Uani 1 1 d . . . C9 C 0.1304(3) -0.0308(5) 0.8702(2) 0.0221(8) Uani 1 1 d . . . H9 H 0.0815 0.0107 0.8858 0.026 Uiso 1 1 calc R . . C10 C 0.2409(3) -0.0306(5) 0.9153(2) 0.0193(8) Uani 1 1 d . . . C11 C 0.3151(3) -0.0873(5) 0.8916(2) 0.0209(8) Uani 1 1 d . . . H11 H 0.3888 -0.0859 0.9212 0.025 Uiso 1 1 calc R . . C12 C 0.2791(3) -0.1461(5) 0.8237(2) 0.0209(8) Uani 1 1 d . . . C13 C 0.1680(3) -0.1481(5) 0.7799(2) 0.0229(9) Uani 1 1 d . . . H13 H 0.1441 -0.1881 0.7347 0.027 Uiso 1 1 calc R . . C14 C 0.2804(3) 0.0383(5) 0.9876(2) 0.0214(8) Uani 1 1 d . . . C15 C 0.3590(3) -0.2030(6) 0.7972(2) 0.0231(9) Uani 1 1 d . . . C16 C 0.1830(4) 0.5640(7) 1.0865(3) 0.0441(13) Uani 1 1 d . . . H16 H 0.2117 0.5740 1.1344 0.053 Uiso 1 1 calc R . . C17 C 0.0637(5) 0.6765(9) 0.9742(3) 0.0550(15) Uani 1 1 d . . . H17A H 0.1028 0.7533 0.9578 0.083 Uiso 1 1 calc R . . H17B H -0.0105 0.7136 0.9557 0.083 Uiso 1 1 calc R . . H17C H 0.0669 0.5585 0.9594 0.083 Uiso 1 1 calc R . . C18 C 0.0824(6) 0.8298(8) 1.0806(3) 0.0629(18) Uani 1 1 d . . . H18A H 0.1215 0.8216 1.1301 0.094 Uiso 1 1 calc R . . H18B H 0.0061 0.8267 1.0673 0.094 Uiso 1 1 calc R . . H18C H 0.1005 0.9380 1.0652 0.094 Uiso 1 1 calc R . . O11 O 0.5047(3) 0.2737(4) 0.9436(2) 0.0367(8) Uani 1 1 d D . . H11A H 0.4776 0.2119 0.9070 0.044 Uiso 1 1 d RD . . H10B H 0.400(5) 0.532(8) 1.201(3) 0.055 Uiso 1 1 d . . . H9A H 0.366(4) -0.105(8) 1.182(3) 0.055 Uiso 1 1 d D . . H9B H 0.450(3) -0.117(6) 1.165(3) 0.055 Uiso 1 1 d D . . H8B H 0.416(5) 0.509(2) 1.0321(13) 0.055 Uiso 1 1 d D . . H11B H 0.553(3) 0.207(3) 0.9730(10) 0.055 Uiso 1 1 d 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 O10 0.0338(19) 0.0385(19) 0.053(2) -0.0226(17) 0.0226(18) -0.0104(16) Tb1 0.01456(13) 0.02080(12) 0.01709(13) -0.00150(7) 0.00752(10) 0.00041(7) O1 0.0188(15) 0.0280(15) 0.0229(15) -0.0053(12) 0.0056(12) 0.0035(12) O2 0.0222(15) 0.0457(19) 0.0271(17) -0.0148(14) 0.0107(14) -0.0001(14) O3 0.0311(19) 0.049(2) 0.0335(19) 0.0037(15) 0.0211(16) 0.0027(15) O4 0.0171(17) 0.056(2) 0.042(2) 0.0009(17) 0.0137(16) -0.0042(15) O5 0.0248(19) 0.089(3) 0.032(2) -0.0178(17) 0.0150(17) 0.0047(17) O6 0.0133(16) 0.070(2) 0.0377(19) -0.0142(18) 0.0078(15) 0.0035(16) O7 0.0373(19) 0.0424(19) 0.0390(19) -0.0010(16) 0.0124(16) 0.0208(16) O8 0.061(2) 0.0296(17) 0.0393(19) 0.0007(15) 0.0350(18) -0.0056(17) O9 0.073(3) 0.0310(18) 0.069(3) 0.0241(18) 0.057(2) 0.0187(19) N1 0.036(2) 0.039(2) 0.037(2) 0.005(2) 0.0176(19) 0.015(2) C1 0.017(2) 0.022(2) 0.021(2) -0.0045(16) 0.0074(17) 0.0010(16) C2 0.019(2) 0.030(2) 0.0175(19) -0.0004(17) 0.0082(17) 0.0041(17) C3 0.019(2) 0.024(2) 0.027(2) -0.0042(17) 0.0129(18) 0.0004(17) C4 0.013(2) 0.046(3) 0.021(2) -0.0011(19) 0.0003(17) -0.0018(19) C5 0.025(2) 0.049(3) 0.019(2) 0.006(2) 0.0065(19) -0.004(2) C6 0.021(2) 0.032(2) 0.025(2) -0.0001(18) 0.0124(18) -0.0050(18) C7 0.022(2) 0.027(2) 0.035(3) 0.001(2) 0.017(2) 0.0038(19) C8 0.017(2) 0.023(2) 0.019(2) -0.0041(16) 0.0080(17) -0.0002(16) C9 0.017(2) 0.022(2) 0.027(2) -0.0038(18) 0.0098(17) 0.0001(17) C10 0.0178(19) 0.0197(19) 0.018(2) -0.0022(16) 0.0061(16) 0.0012(16) C11 0.0133(19) 0.027(2) 0.020(2) -0.0018(16) 0.0047(16) -0.0003(16) C12 0.018(2) 0.021(2) 0.026(2) -0.0018(17) 0.0120(18) -0.0007(16) C13 0.019(2) 0.031(2) 0.019(2) -0.0066(17) 0.0081(17) -0.0041(18) C14 0.023(2) 0.0193(19) 0.021(2) -0.0019(16) 0.0090(18) -0.0008(17) C15 0.019(2) 0.028(2) 0.024(2) -0.0031(18) 0.0113(19) -0.0009(18) C16 0.044(3) 0.052(3) 0.031(3) -0.001(2) 0.011(2) 0.020(3) C17 0.061(4) 0.061(4) 0.041(3) 0.013(3) 0.020(3) 0.014(3) C18 0.081(5) 0.055(4) 0.060(4) 0.004(3) 0.037(4) 0.036(4) O11 0.037(2) 0.0252(16) 0.041(2) 0.0009(14) 0.0109(17) 0.0043(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 O10 Tb1 2.408(3) . ? O10 H10A 0.8500 . ? O10 H10B 0.78(6) . ? Tb1 O6 2.283(3) 3_657 ? Tb1 O3 2.341(3) 3_557 ? Tb1 O7 2.392(3) . ? Tb1 O9 2.406(3) . ? Tb1 O8 2.420(3) . ? Tb1 O2 2.463(3) . ? Tb1 O1 2.470(3) . ? O1 C14 1.273(5) . ? O2 C14 1.264(5) . ? O3 C7 1.276(5) . ? O3 Tb1 2.341(3) 3_557 ? O4 C7 1.260(6) . ? O5 C15 1.253(5) . ? O6 C15 1.248(5) . ? O6 Tb1 2.283(3) 3_657 ? O7 C16 1.239(6) . ? O8 H8A 0.8502 . ? O8 H8B 0.840(10) . ? O9 H9A 0.79(4) . ? O9 H9B 0.848(7) . ? N1 C16 1.317(6) . ? N1 C17 1.444(7) . ? N1 C18 1.456(7) . ? C1 C2 1.393(5) . ? C1 C6 1.400(6) . ? C1 C8 1.498(5) . ? C2 C3 1.407(6) . ? C2 H2 0.9300 . ? C3 C4 1.384(6) . ? C3 C7 1.517(5) . ? C4 C5 1.392(6) . ? C4 H4 0.9300 . ? C5 C6 1.382(6) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.393(6) . ? C8 C13 1.401(5) . ? C9 C10 1.398(6) . ? C9 H9 0.9300 . ? C10 C11 1.394(5) . ? C10 C14 1.498(5) . ? C11 C12 1.392(5) . ? C11 H11 0.9300 . ? C12 C13 1.399(6) . ? C12 C15 1.506(5) . ? C13 H13 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O11 H11A 0.8499 . ? O11 H11B 0.852(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 Tb1 O10 H10A 119.9 . . ? Tb1 O10 H10B 120(5) . . ? H10A O10 H10B 101.4 . . ? O6 Tb1 O3 118.71(13) 3_657 3_557 ? O6 Tb1 O7 143.60(14) 3_657 . ? O3 Tb1 O7 76.19(12) 3_557 . ? O6 Tb1 O9 74.24(15) 3_657 . ? O3 Tb1 O9 74.08(11) 3_557 . ? O7 Tb1 O9 140.98(13) . . ? O6 Tb1 O10 75.06(13) 3_657 . ? O3 Tb1 O10 80.44(12) 3_557 . ? O7 Tb1 O10 75.33(13) . . ? O9 Tb1 O10 122.97(15) . . ? O6 Tb1 O8 79.28(14) 3_657 . ? O3 Tb1 O8 148.60(12) 3_557 . ? O7 Tb1 O8 75.19(12) . . ? O9 Tb1 O8 137.31(11) . . ? O10 Tb1 O8 80.08(12) . . ? O6 Tb1 O2 131.81(11) 3_657 . ? O3 Tb1 O2 97.20(11) 3_557 . ? O7 Tb1 O2 71.81(11) . . ? O9 Tb1 O2 87.42(14) . . ? O10 Tb1 O2 146.61(12) . . ? O8 Tb1 O2 85.93(12) . . ? O6 Tb1 O1 78.95(11) 3_657 . ? O3 Tb1 O1 136.29(11) 3_557 . ? O7 Tb1 O1 114.39(11) . . ? O9 Tb1 O1 73.48(11) . . ? O10 Tb1 O1 142.62(11) . . ? O8 Tb1 O1 68.97(11) . . ? O2 Tb1 O1 53.00(9) . . ? C14 O1 Tb1 92.4(2) . . ? C14 O2 Tb1 93.0(2) . . ? C7 O3 Tb1 135.2(3) . 3_557 ? C15 O6 Tb1 163.8(3) . 3_657 ? C16 O7 Tb1 133.9(3) . . ? Tb1 O8 H8A 119.8 . . ? Tb1 O8 H8B 130.9(18) . . ? H8A O8 H8B 106.8 . . ? Tb1 O9 H9A 127(4) . . ? Tb1 O9 H9B 122(4) . . ? H9A O9 H9B 111(4) . . ? C16 N1 C17 120.9(4) . . ? C16 N1 C18 121.6(5) . . ? C17 N1 C18 117.4(5) . . ? C2 C1 C6 118.7(4) . . ? C2 C1 C8 121.7(4) . . ? C6 C1 C8 119.6(3) . . ? C1 C2 C3 120.8(4) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 119.0(4) . . ? C4 C3 C7 119.6(4) . . ? C2 C3 C7 121.4(4) . . ? C3 C4 C5 120.9(4) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 119.6(4) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 121.0(4) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? O4 C7 O3 124.0(4) . . ? O4 C7 C3 118.6(4) . . ? O3 C7 C3 117.4(4) . . ? C9 C8 C13 117.6(4) . . ? C9 C8 C1 122.5(3) . . ? C13 C8 C1 119.9(3) . . ? C8 C9 C10 121.7(4) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C11 C10 C9 119.5(4) . . ? C11 C10 C14 119.9(4) . . ? C9 C10 C14 120.5(3) . . ? C12 C11 C10 120.1(4) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 119.3(3) . . ? C11 C12 C15 120.4(4) . . ? C13 C12 C15 120.3(4) . . ? C12 C13 C8 121.8(4) . . ? C12 C13 H13 119.1 . . ? C8 C13 H13 119.1 . . ? O2 C14 O1 120.3(4) . . ? O2 C14 C10 120.5(4) . . ? O1 C14 C10 119.1(3) . . ? O6 C15 O5 124.5(4) . . ? O6 C15 C12 118.0(4) . . ? O5 C15 C12 117.5(4) . . ? O7 C16 N1 124.8(5) . . ? O7 C16 H16 117.6 . . ? N1 C16 H16 117.6 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? H11A O11 H11B 103.8 . . ? 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 O6 Tb1 O1 C14 -177.6(3) 3_657 . . . ? O3 Tb1 O1 C14 62.1(3) 3_557 . . . ? O7 Tb1 O1 C14 -33.3(3) . . . . ? O9 Tb1 O1 C14 105.8(3) . . . . ? O10 Tb1 O1 C14 -131.1(3) . . . . ? O8 Tb1 O1 C14 -94.9(2) . . . . ? O2 Tb1 O1 C14 6.3(2) . . . . ? O6 Tb1 O2 C14 -11.4(3) 3_657 . . . ? O3 Tb1 O2 C14 -151.1(2) 3_557 . . . ? O7 Tb1 O2 C14 136.0(3) . . . . ? O9 Tb1 O2 C14 -77.5(2) . . . . ? O10 Tb1 O2 C14 125.3(3) . . . . ? O8 Tb1 O2 C14 60.3(2) . . . . ? O1 Tb1 O2 C14 -6.3(2) . . . . ? O6 Tb1 O7 C16 -68.8(5) 3_657 . . . ? O3 Tb1 O7 C16 51.2(5) 3_557 . . . ? O9 Tb1 O7 C16 92.4(5) . . . . ? O10 Tb1 O7 C16 -32.4(5) . . . . ? O8 Tb1 O7 C16 -115.7(5) . . . . ? O2 Tb1 O7 C16 153.7(5) . . . . ? O1 Tb1 O7 C16 -173.9(5) . . . . ? C6 C1 C2 C3 -0.1(6) . . . . ? C8 C1 C2 C3 -179.2(4) . . . . ? C1 C2 C3 C4 -0.1(6) . . . . ? C1 C2 C3 C7 178.9(4) . . . . ? C2 C3 C4 C5 0.9(7) . . . . ? C7 C3 C4 C5 -178.1(4) . . . . ? C3 C4 C5 C6 -1.4(7) . . . . ? C4 C5 C6 C1 1.2(7) . . . . ? C2 C1 C6 C5 -0.4(6) . . . . ? C8 C1 C6 C5 178.7(4) . . . . ? Tb1 O3 C7 O4 -15.7(7) 3_557 . . . ? Tb1 O3 C7 C3 164.3(3) 3_557 . . . ? C4 C3 C7 O4 7.0(6) . . . . ? C2 C3 C7 O4 -172.0(4) . . . . ? C4 C3 C7 O3 -173.0(4) . . . . ? C2 C3 C7 O3 8.0(6) . . . . ? C2 C1 C8 C9 -38.6(6) . . . . ? C6 C1 C8 C9 142.3(4) . . . . ? C2 C1 C8 C13 142.5(4) . . . . ? C6 C1 C8 C13 -36.5(6) . . . . ? C13 C8 C9 C10 -1.8(6) . . . . ? C1 C8 C9 C10 179.3(4) . . . . ? C8 C9 C10 C11 2.0(6) . . . . ? C8 C9 C10 C14 178.9(4) . . . . ? C9 C10 C11 C12 -0.9(6) . . . . ? C14 C10 C11 C12 -177.9(4) . . . . ? C10 C11 C12 C13 -0.3(6) . . . . ? C10 C11 C12 C15 178.4(4) . . . . ? C11 C12 C13 C8 0.4(6) . . . . ? C15 C12 C13 C8 -178.2(4) . . . . ? C9 C8 C13 C12 0.6(6) . . . . ? C1 C8 C13 C12 179.5(4) . . . . ? Tb1 O2 C14 O1 11.4(4) . . . . ? Tb1 O2 C14 C10 -166.9(3) . . . . ? Tb1 O1 C14 O2 -11.4(4) . . . . ? Tb1 O1 C14 C10 166.9(3) . . . . ? C11 C10 C14 O2 176.3(4) . . . . ? C9 C10 C14 O2 -0.6(6) . . . . ? C11 C10 C14 O1 -2.0(6) . . . . ? C9 C10 C14 O1 -178.9(4) . . . . ? Tb1 O6 C15 O5 -4.5(16) 3_657 . . . ? Tb1 O6 C15 C12 177.9(10) 3_657 . . . ? C11 C12 C15 O6 2.9(6) . . . . ? C13 C12 C15 O6 -178.5(4) . . . . ? C11 C12 C15 O5 -174.9(4) . . . . ? C13 C12 C15 O5 3.7(6) . . . . ? Tb1 O7 C16 N1 168.5(4) . . . . ? C17 N1 C16 O7 -0.3(9) . . . . ? C18 N1 C16 O7 -176.9(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.122 _refine_diff_density_min -0.902 _refine_diff_density_rms 0.109 _database_code_depnum_ccdc_archive 'CCDC 918542'