# 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_global data_nd #TrackingRef 'ND.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H22 N2 Nd2 O18' _chemical_formula_weight 962.96 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' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3604(5) _cell_length_b 8.6125(6) _cell_length_c 12.0452(8) _cell_angle_alpha 74.0980(10) _cell_angle_beta 87.6680(10) _cell_angle_gamma 86.0060(10) _cell_volume 732.37(9) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.183 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 3.599 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2834 _exptl_absorpt_correction_T_max 0.4817 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4469 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3246 _reflns_number_gt 3075 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0354P)^2^+0.2487P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3246 _refine_ls_number_parameters 238 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0239 _refine_ls_R_factor_gt 0.0223 _refine_ls_wR_factor_ref 0.0585 _refine_ls_wR_factor_gt 0.0575 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.043 _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 0.299523(18) 0.188740(17) 0.495866(11) 0.01147(6) Uani 1 1 d . . . O1 O 0.5119(3) 0.0529(3) 0.37739(17) 0.0168(4) Uani 1 1 d . . . O2 O 0.5667(3) -0.1495(3) 0.29888(19) 0.0218(5) Uani 1 1 d . . . O3 O 0.1609(3) -0.0180(3) 0.42897(17) 0.0166(4) Uani 1 1 d . . . O4 O -0.0833(3) -0.0671(3) 0.34362(18) 0.0214(5) Uani 1 1 d . . . O5 O -0.3207(3) 0.6087(3) -0.30761(19) 0.0258(5) Uani 1 1 d . . . O6 O 0.5893(3) 0.3168(3) 0.47865(19) 0.0190(4) Uani 1 1 d . . . O7 O 0.7285(3) 0.5435(3) 0.46396(19) 0.0197(5) Uani 1 1 d . . . O1W O -0.0200(3) 0.2895(3) 0.4326(2) 0.0251(5) Uani 1 1 d D . . H11 H -0.090(4) 0.215(3) 0.462(3) 0.038 Uiso 1 1 d D . . H12 H -0.078(4) 0.379(2) 0.428(4) 0.038 Uiso 1 1 d D . . O2W O -0.6995(5) 0.6214(6) -0.2143(3) 0.0616(10) Uani 1 1 d D . . H21 H -0.774(6) 0.663(8) -0.266(3) 0.092 Uiso 1 1 d D . . H22 H -0.593(3) 0.621(8) -0.242(4) 0.092 Uiso 1 1 d D . . N1 N -0.0093(4) 0.2891(3) -0.0642(2) 0.0198(5) Uani 1 1 d . . . C1 C 0.4830(4) -0.0195(4) 0.3002(2) 0.0151(6) Uani 1 1 d . . . C2 C 0.3471(4) 0.0550(4) 0.2058(2) 0.0160(6) Uani 1 1 d . . . C3 C 0.1583(4) 0.0566(4) 0.2246(2) 0.0152(6) Uani 1 1 d . . . C4 C 0.0425(4) 0.1244(4) 0.1321(3) 0.0183(6) Uani 1 1 d . . . H4 H -0.0831 0.1203 0.1435 0.022 Uiso 1 1 calc R . . C5 C 0.1142(4) 0.1975(4) 0.0238(2) 0.0191(6) Uani 1 1 d . . . C6 C 0.3002(4) 0.1901(4) 0.0024(2) 0.0236(7) Uani 1 1 d . . . H6 H 0.3476 0.2330 -0.0715 0.028 Uiso 1 1 calc R . . C7 C 0.4153(4) 0.1173(4) 0.0936(3) 0.0220(7) Uani 1 1 d . . . H7 H 0.5403 0.1100 0.0794 0.026 Uiso 1 1 calc R . . C8 C 0.0712(4) -0.0151(4) 0.3409(2) 0.0149(6) Uani 1 1 d . . . C9 C -0.1539(5) 0.3784(4) -0.0336(3) 0.0255(7) Uani 1 1 d . . . H9 H -0.1769 0.3703 0.0443 0.031 Uiso 1 1 calc R . . C10 C -0.2647(5) 0.4782(5) -0.1129(3) 0.0274(8) Uani 1 1 d . . . H10 H -0.3652 0.5326 -0.0883 0.033 Uiso 1 1 calc R . . C11 C -0.2302(4) 0.5016(4) -0.2340(3) 0.0189(6) Uani 1 1 d . . . C12 C -0.0881(5) 0.3957(4) -0.2614(3) 0.0227(7) Uani 1 1 d . . . H12A H -0.0683 0.3943 -0.3379 0.027 Uiso 1 1 calc R . . C13 C 0.0193(4) 0.2967(4) -0.1785(3) 0.0213(6) Uani 1 1 d . . . H13 H 0.1140 0.2329 -0.1999 0.026 Uiso 1 1 calc R . . C14 C 0.5909(4) 0.4590(4) 0.4836(2) 0.0148(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Nd1 0.00926(9) 0.01218(10) 0.01251(9) -0.00291(6) -0.00241(5) 0.00199(6) O1 0.0151(10) 0.0214(12) 0.0146(10) -0.0066(8) -0.0048(8) 0.0041(8) O2 0.0196(11) 0.0220(12) 0.0255(11) -0.0104(10) -0.0076(9) 0.0080(9) O3 0.0170(10) 0.0202(12) 0.0129(10) -0.0043(8) -0.0027(8) -0.0016(9) O4 0.0142(10) 0.0330(14) 0.0172(10) -0.0067(9) -0.0001(8) -0.0045(9) O5 0.0215(11) 0.0272(13) 0.0214(11) 0.0037(10) -0.0032(9) 0.0081(10) O6 0.0121(10) 0.0156(11) 0.0306(12) -0.0088(9) -0.0014(8) 0.0005(8) O7 0.0127(10) 0.0163(11) 0.0312(12) -0.0090(9) 0.0001(9) 0.0013(8) O1W 0.0134(10) 0.0190(12) 0.0376(14) 0.0005(10) 0.0015(9) 0.0019(9) O2W 0.0421(18) 0.114(3) 0.0283(16) -0.0187(19) 0.0041(13) -0.004(2) N1 0.0191(13) 0.0238(15) 0.0143(12) -0.0025(10) -0.0043(10) 0.0060(11) C1 0.0103(12) 0.0209(16) 0.0112(13) 0.0000(11) -0.0006(10) 0.0021(11) C2 0.0153(14) 0.0191(16) 0.0128(13) -0.0038(11) -0.0025(11) 0.0023(12) C3 0.0161(14) 0.0148(15) 0.0141(13) -0.0030(11) -0.0020(11) 0.0011(11) C4 0.0129(13) 0.0255(17) 0.0154(14) -0.0037(12) -0.0033(11) 0.0011(12) C5 0.0204(15) 0.0231(17) 0.0129(14) -0.0039(12) -0.0052(11) 0.0040(13) C6 0.0250(18) 0.030(2) 0.0125(15) -0.0014(13) 0.0000(13) 0.0028(15) C7 0.0136(14) 0.0348(19) 0.0156(14) -0.0052(13) 0.0010(11) 0.0042(13) C8 0.0153(13) 0.0150(15) 0.0144(13) -0.0046(11) -0.0016(10) 0.0030(11) C9 0.0284(17) 0.0310(19) 0.0139(15) -0.0036(13) -0.0019(12) 0.0110(15) C10 0.0257(17) 0.032(2) 0.0195(16) -0.0033(14) -0.0001(13) 0.0132(15) C11 0.0173(14) 0.0182(16) 0.0186(15) -0.0009(12) -0.0028(11) 0.0021(12) C12 0.0259(16) 0.0260(18) 0.0143(14) -0.0040(12) -0.0015(12) 0.0053(14) C13 0.0243(16) 0.0218(17) 0.0168(14) -0.0048(12) -0.0019(12) 0.0032(13) C14 0.0131(13) 0.0156(15) 0.0149(13) -0.0030(11) -0.0021(10) 0.0014(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Nd1 O3 2.443(2) . ? Nd1 O6 2.445(2) . ? Nd1 O5 2.460(2) 2_565 ? Nd1 O7 2.476(2) 2_666 ? Nd1 O4 2.498(2) 2_556 ? Nd1 O1 2.515(2) . ? Nd1 O1W 2.522(2) . ? Nd1 O1 2.573(2) 2_656 ? Nd1 O2 2.625(2) 2_656 ? Nd1 C1 2.959(3) 2_656 ? O1 C1 1.285(4) . ? O1 Nd1 2.573(2) 2_656 ? O2 C1 1.243(4) . ? O2 Nd1 2.625(2) 2_656 ? O3 C8 1.266(3) . ? O4 C8 1.247(4) . ? O4 Nd1 2.498(2) 2_556 ? O5 C11 1.263(4) . ? O5 Nd1 2.460(2) 2_565 ? O6 C14 1.243(4) . ? O7 C14 1.265(4) . ? O7 Nd1 2.476(2) 2_666 ? O1W H11 0.839(10) . ? O1W H12 0.843(10) . ? O2W H21 0.835(10) . ? O2W H22 0.838(10) . ? N1 C13 1.368(4) . ? N1 C9 1.368(4) . ? N1 C5 1.447(4) . ? C1 C2 1.519(4) . ? C1 Nd1 2.959(3) 2_656 ? C2 C3 1.398(4) . ? C2 C7 1.397(4) . ? C3 C4 1.400(4) . ? C3 C8 1.504(4) . ? C4 C5 1.385(4) . ? C4 H4 0.9300 . ? C5 C6 1.383(4) . ? C6 C7 1.393(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C10 1.354(4) . ? C9 H9 0.9300 . ? C10 C11 1.431(4) . ? C10 H10 0.9300 . ? C11 C12 1.428(4) . ? C12 C13 1.361(4) . ? C12 H12A 0.9300 . ? C13 H13 0.9300 . ? C14 C14 1.556(5) 2_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Nd1 O6 139.20(7) . . ? O3 Nd1 O5 97.37(8) . 2_565 ? O6 Nd1 O5 70.41(8) . 2_565 ? O3 Nd1 O7 148.95(7) . 2_666 ? O6 Nd1 O7 66.76(7) . 2_666 ? O5 Nd1 O7 73.65(8) 2_565 2_666 ? O3 Nd1 O4 76.13(7) . 2_556 ? O6 Nd1 O4 136.15(7) . 2_556 ? O5 Nd1 O4 143.35(7) 2_565 2_556 ? O7 Nd1 O4 93.30(8) 2_666 2_556 ? O3 Nd1 O1 66.09(7) . . ? O6 Nd1 O1 73.14(7) . . ? O5 Nd1 O1 75.90(7) 2_565 . ? O7 Nd1 O1 135.70(7) 2_666 . ? O4 Nd1 O1 129.55(8) 2_556 . ? O3 Nd1 O1W 71.19(8) . . ? O6 Nd1 O1W 133.93(8) . . ? O5 Nd1 O1W 72.09(8) 2_565 . ? O7 Nd1 O1W 77.78(8) 2_666 . ? O4 Nd1 O1W 71.70(8) 2_556 . ? O1 Nd1 O1W 121.60(7) . . ? O3 Nd1 O1 84.15(7) . 2_656 ? O6 Nd1 O1 82.26(7) . 2_656 ? O5 Nd1 O1 139.69(7) 2_565 2_656 ? O7 Nd1 O1 122.17(7) 2_666 2_656 ? O4 Nd1 O1 76.31(7) 2_556 2_656 ? O1 Nd1 O1 67.97(7) . 2_656 ? O1W Nd1 O1 143.27(7) . 2_656 ? O3 Nd1 O2 125.90(7) . 2_656 ? O6 Nd1 O2 69.82(7) . 2_656 ? O5 Nd1 O2 135.55(8) 2_565 2_656 ? O7 Nd1 O2 73.07(7) 2_666 2_656 ? O4 Nd1 O2 67.01(7) 2_556 2_656 ? O1 Nd1 O2 110.11(6) . 2_656 ? O1W Nd1 O2 127.03(7) . 2_656 ? O1 Nd1 O2 50.24(6) 2_656 2_656 ? O3 Nd1 C1 107.26(8) . 2_656 ? O6 Nd1 C1 72.05(8) . 2_656 ? O5 Nd1 C1 142.02(8) 2_565 2_656 ? O7 Nd1 C1 96.70(8) 2_666 2_656 ? O4 Nd1 C1 72.18(7) 2_556 2_656 ? O1 Nd1 C1 88.01(7) . 2_656 ? O1W Nd1 C1 143.02(8) . 2_656 ? O1 Nd1 C1 25.67(7) 2_656 2_656 ? O2 Nd1 C1 24.81(7) 2_656 2_656 ? C1 O1 Nd1 132.15(18) . . ? C1 O1 Nd1 94.20(17) . 2_656 ? Nd1 O1 Nd1 112.03(7) . 2_656 ? C1 O2 Nd1 92.80(17) . 2_656 ? C8 O3 Nd1 133.9(2) . . ? C8 O4 Nd1 133.32(19) . 2_556 ? C11 O5 Nd1 143.7(2) . 2_565 ? C14 O6 Nd1 119.57(18) . . ? C14 O7 Nd1 118.09(18) . 2_666 ? Nd1 O1W H11 108(3) . . ? Nd1 O1W H12 131(3) . . ? H11 O1W H12 108.2(17) . . ? H21 O2W H22 110.0(18) . . ? C13 N1 C9 118.6(3) . . ? C13 N1 C5 122.1(3) . . ? C9 N1 C5 119.1(2) . . ? O2 C1 O1 121.6(3) . . ? O2 C1 C2 118.2(3) . . ? O1 C1 C2 120.2(3) . . ? O2 C1 Nd1 62.38(15) . 2_656 ? O1 C1 Nd1 60.13(14) . 2_656 ? C2 C1 Nd1 171.4(2) . 2_656 ? C3 C2 C7 118.7(3) . . ? C3 C2 C1 123.4(3) . . ? C7 C2 C1 117.8(3) . . ? C4 C3 C2 119.7(3) . . ? C4 C3 C8 117.4(3) . . ? C2 C3 C8 122.8(3) . . ? C5 C4 C3 120.2(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 120.6(3) . . ? C6 C5 N1 121.0(3) . . ? C4 C5 N1 118.3(3) . . ? C5 C6 C7 118.9(3) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C6 C7 C2 121.5(3) . . ? C6 C7 H7 119.3 . . ? C2 C7 H7 119.3 . . ? O4 C8 O3 124.9(3) . . ? O4 C8 C3 117.9(3) . . ? O3 C8 C3 117.3(3) . . ? C10 C9 N1 122.0(3) . . ? C10 C9 H9 119.0 . . ? N1 C9 H9 119.0 . . ? C9 C10 C11 121.3(3) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? O5 C11 C12 124.7(3) . . ? O5 C11 C10 121.0(3) . . ? C12 C11 C10 114.3(3) . . ? C13 C12 C11 121.7(3) . . ? C13 C12 H12A 119.1 . . ? C11 C12 H12A 119.1 . . ? N1 C13 C12 121.4(3) . . ? N1 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? O6 C14 O7 125.4(3) . . ? O6 C14 C14 117.7(3) . 2_666 ? O7 C14 C14 116.9(3) . 2_666 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Nd1 O1 C1 24.8(2) . . . . ? O6 Nd1 O1 C1 -153.4(3) . . . . ? O5 Nd1 O1 C1 -80.0(3) 2_565 . . . ? O7 Nd1 O1 C1 -127.7(2) 2_666 . . . ? O4 Nd1 O1 C1 69.9(3) 2_556 . . . ? O1W Nd1 O1 C1 -21.8(3) . . . . ? O1 Nd1 O1 C1 118.2(3) 2_656 . . . ? O2 Nd1 O1 C1 146.2(2) 2_656 . . . ? C1 Nd1 O1 C1 134.7(2) 2_656 . . . ? O3 Nd1 O1 Nd1 -93.39(9) . . . 2_656 ? O6 Nd1 O1 Nd1 88.33(9) . . . 2_656 ? O5 Nd1 O1 Nd1 161.77(10) 2_565 . . 2_656 ? O7 Nd1 O1 Nd1 114.06(10) 2_666 . . 2_656 ? O4 Nd1 O1 Nd1 -48.30(12) 2_556 . . 2_656 ? O1W Nd1 O1 Nd1 -140.01(8) . . . 2_656 ? O1 Nd1 O1 Nd1 0.0 2_656 . . 2_656 ? O2 Nd1 O1 Nd1 27.99(10) 2_656 . . 2_656 ? C1 Nd1 O1 Nd1 16.49(9) 2_656 . . 2_656 ? O6 Nd1 O3 C8 -89.7(3) . . . . ? O5 Nd1 O3 C8 -21.3(3) 2_565 . . . ? O7 Nd1 O3 C8 49.1(3) 2_666 . . . ? O4 Nd1 O3 C8 122.0(3) 2_556 . . . ? O1 Nd1 O3 C8 -92.3(3) . . . . ? O1W Nd1 O3 C8 46.9(2) . . . . ? O1 Nd1 O3 C8 -160.7(3) 2_656 . . . ? O2 Nd1 O3 C8 169.5(2) 2_656 . . . ? C1 Nd1 O3 C8 -172.0(2) 2_656 . . . ? O3 Nd1 O6 C14 150.17(19) . . . . ? O5 Nd1 O6 C14 71.9(2) 2_565 . . . ? O7 Nd1 O6 C14 -8.2(2) 2_666 . . . ? O4 Nd1 O6 C14 -77.3(2) 2_556 . . . ? O1 Nd1 O6 C14 152.6(2) . . . . ? O1W Nd1 O6 C14 34.7(3) . . . . ? O1 Nd1 O6 C14 -138.2(2) 2_656 . . . ? O2 Nd1 O6 C14 -87.8(2) 2_656 . . . ? C1 Nd1 O6 C14 -114.0(2) 2_656 . . . ? Nd1 O2 C1 O1 11.1(3) 2_656 . . . ? Nd1 O2 C1 C2 -170.3(2) 2_656 . . . ? Nd1 O1 C1 O2 -136.4(2) . . . . ? Nd1 O1 C1 O2 -11.4(3) 2_656 . . . ? Nd1 O1 C1 C2 45.0(4) . . . . ? Nd1 O1 C1 C2 170.0(2) 2_656 . . . ? Nd1 O1 C1 Nd1 -125.0(2) . . . 2_656 ? O2 C1 C2 C3 107.1(3) . . . . ? O1 C1 C2 C3 -74.3(4) . . . . ? Nd1 C1 C2 C3 15.3(16) 2_656 . . . ? O2 C1 C2 C7 -69.4(4) . . . . ? O1 C1 C2 C7 109.2(3) . . . . ? Nd1 C1 C2 C7 -161.2(13) 2_656 . . . ? C7 C2 C3 C4 -2.0(5) . . . . ? C1 C2 C3 C4 -178.4(3) . . . . ? C7 C2 C3 C8 176.8(3) . . . . ? C1 C2 C3 C8 0.3(5) . . . . ? C2 C3 C4 C5 -3.5(5) . . . . ? C8 C3 C4 C5 177.7(3) . . . . ? C3 C4 C5 C6 6.7(5) . . . . ? C3 C4 C5 N1 -169.9(3) . . . . ? C13 N1 C5 C6 36.7(5) . . . . ? C9 N1 C5 C6 -139.6(3) . . . . ? C13 N1 C5 C4 -146.7(3) . . . . ? C9 N1 C5 C4 37.1(4) . . . . ? C4 C5 C6 C7 -4.3(5) . . . . ? N1 C5 C6 C7 172.3(3) . . . . ? C5 C6 C7 C2 -1.3(5) . . . . ? C3 C2 C7 C6 4.4(5) . . . . ? C1 C2 C7 C6 -178.9(3) . . . . ? Nd1 O4 C8 O3 2.2(5) 2_556 . . . ? Nd1 O4 C8 C3 -177.75(19) 2_556 . . . ? Nd1 O3 C8 O4 -124.3(3) . . . . ? Nd1 O3 C8 C3 55.6(4) . . . . ? C4 C3 C8 O4 26.9(4) . . . . ? C2 C3 C8 O4 -151.8(3) . . . . ? C4 C3 C8 O3 -153.0(3) . . . . ? C2 C3 C8 O3 28.2(4) . . . . ? C13 N1 C9 C10 -2.6(5) . . . . ? C5 N1 C9 C10 173.8(3) . . . . ? N1 C9 C10 C11 -3.2(6) . . . . ? Nd1 O5 C11 C12 -37.3(6) 2_565 . . . ? Nd1 O5 C11 C10 142.4(3) 2_565 . . . ? C9 C10 C11 O5 -171.5(4) . . . . ? C9 C10 C11 C12 8.2(5) . . . . ? O5 C11 C12 C13 171.7(3) . . . . ? C10 C11 C12 C13 -8.0(5) . . . . ? C9 N1 C13 C12 2.8(5) . . . . ? C5 N1 C13 C12 -173.5(3) . . . . ? C11 C12 C13 N1 2.8(5) . . . . ? Nd1 O6 C14 O7 -172.2(2) . . . . ? Nd1 O6 C14 C14 7.6(4) . . . 2_666 ? Nd1 O7 C14 O6 -172.5(2) 2_666 . . . ? Nd1 O7 C14 C14 7.7(4) 2_666 . . 2_666 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H11 O3 0.839(10) 1.931(19) 2.718(3) 156(4) 2_556 O1W H12 O7 0.843(10) 2.057(17) 2.861(3) 160(3) 1_455 O2W H22 O5 0.838(10) 2.132(11) 2.969(4) 177(6) . _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 1.186 _refine_diff_density_min -1.107 _refine_diff_density_rms 0.116 _database_code_depnum_ccdc_archive 'CCDC 922525' data_sm #TrackingRef 'SM.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 N O9 Sm' _chemical_formula_weight 487.59 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' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2867(4) _cell_length_b 8.5143(5) _cell_length_c 12.0238(7) _cell_angle_alpha 73.9876(8) _cell_angle_beta 87.9715(8) _cell_angle_gamma 85.9747(8) _cell_volume 715.16(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 4.161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.281 _exptl_absorpt_correction_T_max 0.304 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4350 _diffrn_reflns_av_R_equivalents 0.0139 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3172 _reflns_number_gt 3089 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.4832P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3172 _refine_ls_number_parameters 238 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0222 _refine_ls_R_factor_gt 0.0217 _refine_ls_wR_factor_ref 0.0564 _refine_ls_wR_factor_gt 0.0561 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.045 _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 0.300589(16) 0.188733(14) 0.495406(11) 0.01029(6) Uani 1 1 d . . . O1 O 0.5129(3) 0.0517(2) 0.37912(18) 0.0154(4) Uani 1 1 d . . . O2 O 0.5658(3) -0.1520(3) 0.30066(19) 0.0205(4) Uani 1 1 d . . . O3 O 0.1608(3) -0.0163(2) 0.42968(17) 0.0147(4) Uani 1 1 d . . . O4 O -0.0855(3) -0.0687(3) 0.34538(18) 0.0199(4) Uani 1 1 d . . . O5 O -0.3223(3) 0.6111(3) -0.30869(19) 0.0232(5) Uani 1 1 d . . . O6 O 0.5897(3) 0.3162(2) 0.47871(19) 0.0173(4) Uani 1 1 d . . . O7 O 0.7297(3) 0.5442(2) 0.46507(19) 0.0173(4) Uani 1 1 d . . . O1W O -0.0172(3) 0.2893(3) 0.4326(2) 0.0219(5) Uani 1 1 d D . . H11 H -0.090(4) 0.215(3) 0.457(4) 0.033 Uiso 1 1 d D . . H12 H -0.065(5) 0.378(2) 0.440(4) 0.033 Uiso 1 1 d D . . O2W O -0.7019(5) 0.6223(6) -0.2149(3) 0.0563(9) Uani 1 1 d D . . H21 H -0.780(6) 0.657(8) -0.267(3) 0.084 Uiso 1 1 d D . . H22 H -0.600(4) 0.602(8) -0.244(4) 0.084 Uiso 1 1 d D . . N1 N -0.0110(4) 0.2890(3) -0.0644(2) 0.0183(5) Uani 1 1 d . . . C1 C 0.4826(4) -0.0205(3) 0.3021(2) 0.0131(5) Uani 1 1 d . . . C2 C 0.3476(4) 0.0544(3) 0.2068(2) 0.0146(5) Uani 1 1 d . . . C3 C 0.1572(4) 0.0566(3) 0.2255(2) 0.0142(5) Uani 1 1 d . . . C4 C 0.0407(4) 0.1247(4) 0.1331(3) 0.0170(6) Uani 1 1 d . . . H4 H -0.0861 0.1217 0.1446 0.020 Uiso 1 1 calc R . . C5 C 0.1122(4) 0.1970(4) 0.0243(2) 0.0176(6) Uani 1 1 d . . . C6 C 0.3004(4) 0.1888(4) 0.0035(2) 0.0227(7) Uani 1 1 d . . . H6 H 0.3484 0.2314 -0.0706 0.027 Uiso 1 1 calc R . . C7 C 0.4159(4) 0.1159(4) 0.0950(3) 0.0208(6) Uani 1 1 d . . . H7 H 0.5421 0.1079 0.0813 0.025 Uiso 1 1 calc R . . C8 C 0.0700(4) -0.0148(3) 0.3421(2) 0.0137(5) Uani 1 1 d . . . C9 C -0.1566(5) 0.3781(4) -0.0334(3) 0.0245(7) Uani 1 1 d . . . H9 H -0.1800 0.3692 0.0446 0.029 Uiso 1 1 calc R . . C10 C -0.2679(5) 0.4793(4) -0.1138(3) 0.0253(7) Uani 1 1 d . . . H10 H -0.3698 0.5346 -0.0900 0.030 Uiso 1 1 calc R . . C11 C -0.2315(4) 0.5026(4) -0.2344(3) 0.0183(6) Uani 1 1 d . . . C12 C -0.0899(4) 0.3964(4) -0.2622(3) 0.0198(6) Uani 1 1 d . . . H12A H -0.0702 0.3954 -0.3388 0.024 Uiso 1 1 calc R . . C13 C 0.0184(4) 0.2954(4) -0.1778(3) 0.0194(6) Uani 1 1 d . . . H13 H 0.1138 0.2300 -0.1984 0.023 Uiso 1 1 calc R . . C14 C 0.5918(4) 0.4599(3) 0.4837(2) 0.0133(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 ND1 0.00937(8) 0.01033(8) 0.01114(9) -0.00291(6) -0.00107(5) -0.00010(5) O1 0.0129(9) 0.0185(10) 0.0153(10) -0.0059(8) -0.0045(7) 0.0027(8) O2 0.0202(10) 0.0201(10) 0.0226(11) -0.0090(9) -0.0072(9) 0.0058(8) O3 0.0153(9) 0.0182(10) 0.0105(9) -0.0034(8) -0.0012(7) -0.0023(8) O4 0.0143(10) 0.0304(11) 0.0151(10) -0.0050(9) 0.0002(8) -0.0074(9) O5 0.0222(11) 0.0243(11) 0.0164(11) 0.0044(9) -0.0023(9) 0.0054(9) O6 0.0132(9) 0.0138(9) 0.0271(11) -0.0092(9) 0.0012(8) -0.0009(8) O7 0.0122(9) 0.0146(9) 0.0275(11) -0.0100(9) 0.0027(8) -0.0009(7) O1W 0.0128(10) 0.0167(10) 0.0317(13) 0.0003(9) 0.0014(9) 0.0007(8) O2W 0.0421(18) 0.101(3) 0.0263(15) -0.0190(18) 0.0078(13) -0.0065(19) N1 0.0192(12) 0.0204(12) 0.0132(12) -0.0022(10) -0.0031(10) 0.0041(10) C1 0.0099(11) 0.0162(13) 0.0112(12) -0.0002(10) -0.0007(10) -0.0013(10) C2 0.0142(13) 0.0167(13) 0.0126(13) -0.0040(11) -0.0020(10) 0.0016(10) C3 0.0153(13) 0.0143(12) 0.0124(13) -0.0028(11) -0.0009(10) 0.0002(10) C4 0.0144(13) 0.0204(14) 0.0150(14) -0.0033(11) -0.0012(11) 0.0019(11) C5 0.0197(14) 0.0199(14) 0.0121(13) -0.0031(11) -0.0049(11) 0.0024(11) C6 0.0236(17) 0.0295(18) 0.0120(14) -0.0016(13) 0.0032(12) 0.0002(14) C7 0.0170(14) 0.0276(15) 0.0156(14) -0.0036(12) 0.0021(11) 0.0024(12) C8 0.0157(13) 0.0129(12) 0.0123(13) -0.0036(10) -0.0006(10) 0.0019(10) C9 0.0272(16) 0.0315(17) 0.0126(14) -0.0047(13) 0.0002(12) 0.0078(13) C10 0.0258(16) 0.0277(16) 0.0186(15) -0.0031(13) 0.0009(12) 0.0113(13) C11 0.0187(14) 0.0187(13) 0.0153(14) -0.0005(11) -0.0035(11) -0.0016(11) C12 0.0258(15) 0.0208(14) 0.0110(13) -0.0016(11) -0.0047(11) 0.0025(12) C13 0.0225(14) 0.0216(14) 0.0130(13) -0.0039(11) -0.0018(11) 0.0035(12) C14 0.0124(13) 0.0143(12) 0.0127(13) -0.0033(10) -0.0003(10) 0.0009(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sm1 O3 2.404(2) . ? Sm1 O6 2.414(2) . ? Sm1 O5 2.423(2) 2_565 ? Sm1 O7 2.442(2) 2_666 ? Sm1 O4 2.470(2) 2_556 ? Sm1 O1W 2.481(2) . ? Sm1 O1 2.491(2) . ? Sm1 O1 2.5225(19) 2_656 ? Sm1 O2 2.600(2) 2_656 ? Sm1 C1 2.917(3) 2_656 ? O1 C1 1.278(3) . ? O1 Sm1 2.5225(19) 2_656 ? O2 C1 1.240(4) . ? O2 Sm1 2.600(2) 2_656 ? O3 C8 1.260(3) . ? O4 C8 1.247(4) . ? O4 Sm1 2.470(2) 2_556 ? O5 C11 1.261(4) . ? O5 Sm1 2.423(2) 2_565 ? O6 C14 1.242(3) . ? O7 C14 1.254(3) . ? O7 Sm1 2.442(2) 2_666 ? O1W H11 0.837(10) . ? O1W H12 0.836(10) . ? O2W H21 0.836(10) . ? O2W H22 0.838(10) . ? N1 C13 1.360(4) . ? N1 C9 1.362(4) . ? N1 C5 1.437(4) . ? C1 C2 1.508(4) . ? C1 Sm1 2.917(3) 2_656 ? C2 C7 1.389(4) . ? C2 C3 1.397(4) . ? C3 C4 1.391(4) . ? C3 C8 1.503(4) . ? C4 C5 1.384(4) . ? C4 H4 0.9300 . ? C5 C6 1.385(4) . ? C6 C7 1.385(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C9 C10 1.354(4) . ? C9 H9 0.9300 . ? C10 C11 1.426(4) . ? C10 H10 0.9300 . ? C11 C12 1.416(4) . ? C12 C13 1.368(4) . ? C12 H12A 0.9300 . ? C13 H13 0.9300 . ? C14 C14 1.547(5) 2_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Sm1 O6 139.46(7) . . ? O3 Sm1 O5 97.07(8) . 2_565 ? O6 Sm1 O5 70.40(8) . 2_565 ? O3 Sm1 O7 148.26(7) . 2_666 ? O6 Sm1 O7 67.24(7) . 2_666 ? O5 Sm1 O7 74.24(8) 2_565 2_666 ? O3 Sm1 O4 76.28(7) . 2_556 ? O6 Sm1 O4 135.91(7) . 2_556 ? O5 Sm1 O4 143.62(7) 2_565 2_556 ? O7 Sm1 O4 92.63(7) 2_666 2_556 ? O3 Sm1 O1W 70.89(7) . . ? O6 Sm1 O1W 134.01(7) . . ? O5 Sm1 O1W 72.41(7) 2_565 . ? O7 Sm1 O1W 77.41(7) 2_666 . ? O4 Sm1 O1W 71.64(7) 2_556 . ? O3 Sm1 O1 66.42(7) . . ? O6 Sm1 O1 73.09(7) . . ? O5 Sm1 O1 75.59(7) 2_565 . ? O7 Sm1 O1 136.17(7) 2_666 . ? O4 Sm1 O1 129.72(7) 2_556 . ? O1W Sm1 O1 121.80(7) . . ? O3 Sm1 O1 84.28(7) . 2_656 ? O6 Sm1 O1 82.39(7) . 2_656 ? O5 Sm1 O1 139.44(7) 2_565 2_656 ? O7 Sm1 O1 122.39(7) 2_666 2_656 ? O4 Sm1 O1 76.25(7) 2_556 2_656 ? O1W Sm1 O1 143.05(7) . 2_656 ? O1 Sm1 O1 67.87(8) . 2_656 ? O3 Sm1 O2 126.40(7) . 2_656 ? O6 Sm1 O2 69.73(7) . 2_656 ? O5 Sm1 O2 135.43(8) 2_565 2_656 ? O7 Sm1 O2 72.65(7) 2_666 2_656 ? O4 Sm1 O2 66.84(7) 2_556 2_656 ? O1W Sm1 O2 126.63(8) . 2_656 ? O1 Sm1 O2 110.36(7) . 2_656 ? O1 Sm1 O2 50.77(6) 2_656 2_656 ? O3 Sm1 C1 107.57(7) . 2_656 ? O6 Sm1 C1 72.03(7) . 2_656 ? O5 Sm1 C1 141.95(8) 2_565 2_656 ? O7 Sm1 C1 96.67(8) 2_666 2_656 ? O4 Sm1 C1 72.03(7) 2_556 2_656 ? O1W Sm1 C1 142.82(8) . 2_656 ? O1 Sm1 C1 88.02(7) . 2_656 ? O1 Sm1 C1 25.89(7) 2_656 2_656 ? O2 Sm1 C1 25.13(7) 2_656 2_656 ? C1 O1 Sm1 131.69(17) . . ? C1 O1 Sm1 94.57(16) . 2_656 ? Sm1 O1 Sm1 112.13(8) . 2_656 ? C1 O2 Sm1 91.87(17) . 2_656 ? C8 O3 Sm1 134.56(18) . . ? C8 O4 Sm1 133.46(19) . 2_556 ? C11 O5 Sm1 143.7(2) . 2_565 ? C14 O6 Sm1 119.66(17) . . ? C14 O7 Sm1 117.76(17) . 2_666 ? Sm1 O1W H11 111(3) . . ? Sm1 O1W H12 122(3) . . ? H11 O1W H12 109.4(17) . . ? H21 O2W H22 109.8(18) . . ? C13 N1 C9 119.5(3) . . ? C13 N1 C5 122.1(3) . . ? C9 N1 C5 118.3(3) . . ? O2 C1 O1 121.6(2) . . ? O2 C1 C2 117.4(3) . . ? O1 C1 C2 121.0(2) . . ? O2 C1 Sm1 62.99(15) . 2_656 ? O1 C1 Sm1 59.54(13) . 2_656 ? C2 C1 Sm1 171.86(19) . 2_656 ? C7 C2 C3 118.9(3) . . ? C7 C2 C1 118.4(3) . . ? C3 C2 C1 122.7(3) . . ? C4 C3 C2 119.6(3) . . ? C4 C3 C8 117.5(3) . . ? C2 C3 C8 122.9(3) . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.4(3) . . ? C4 C5 N1 118.8(3) . . ? C6 C5 N1 120.7(3) . . ? C7 C6 C5 118.9(3) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C2 121.6(3) . . ? C6 C7 H7 119.2 . . ? C2 C7 H7 119.2 . . ? O4 C8 O3 124.9(3) . . ? O4 C8 C3 118.1(3) . . ? O3 C8 C3 117.1(3) . . ? C10 C9 N1 121.3(3) . . ? C10 C9 H9 119.3 . . ? N1 C9 H9 119.3 . . ? C9 C10 C11 121.1(3) . . ? C9 C10 H10 119.4 . . ? C11 C10 H10 119.4 . . ? O5 C11 C12 123.9(3) . . ? O5 C11 C10 120.7(3) . . ? C12 C11 C10 115.3(3) . . ? C13 C12 C11 120.9(3) . . ? C13 C12 H12A 119.6 . . ? C11 C12 H12A 119.6 . . ? N1 C13 C12 121.2(3) . . ? N1 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? O6 C14 O7 125.5(2) . . ? O6 C14 C14 116.8(3) . 2_666 ? O7 C14 C14 117.6(3) . 2_666 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 Sm1 O1 C1 25.1(2) . . . . ? O6 Sm1 O1 C1 -153.0(2) . . . . ? O5 Sm1 O1 C1 -79.4(2) 2_565 . . . ? O7 Sm1 O1 C1 -127.2(2) 2_666 . . . ? O4 Sm1 O1 C1 70.7(2) 2_556 . . . ? O1W Sm1 O1 C1 -21.2(3) . . . . ? O1 Sm1 O1 C1 118.5(3) 2_656 . . . ? O2 Sm1 O1 C1 147.0(2) 2_656 . . . ? C1 Sm1 O1 C1 135.2(2) 2_656 . . . ? O3 Sm1 O1 Sm1 -93.44(9) . . . 2_656 ? O6 Sm1 O1 Sm1 88.52(9) . . . 2_656 ? O5 Sm1 O1 Sm1 162.03(10) 2_565 . . 2_656 ? O7 Sm1 O1 Sm1 114.29(10) 2_666 . . 2_656 ? O4 Sm1 O1 Sm1 -47.82(12) 2_556 . . 2_656 ? O1W Sm1 O1 Sm1 -139.73(8) . . . 2_656 ? O1 Sm1 O1 Sm1 0.0 2_656 . . 2_656 ? O2 Sm1 O1 Sm1 28.47(10) 2_656 . . 2_656 ? C1 Sm1 O1 Sm1 16.71(8) 2_656 . . 2_656 ? O6 Sm1 O3 C8 -89.4(3) . . . . ? O5 Sm1 O3 C8 -21.5(3) 2_565 . . . ? O7 Sm1 O3 C8 49.9(3) 2_666 . . . ? O4 Sm1 O3 C8 122.1(3) 2_556 . . . ? O1W Sm1 O3 C8 47.1(3) . . . . ? O1 Sm1 O3 C8 -92.3(3) . . . . ? O1 Sm1 O3 C8 -160.7(3) 2_656 . . . ? O2 Sm1 O3 C8 169.1(2) 2_656 . . . ? C1 Sm1 O3 C8 -172.1(2) 2_656 . . . ? O3 Sm1 O6 C14 150.14(19) . . . . ? O5 Sm1 O6 C14 72.6(2) 2_565 . . . ? O7 Sm1 O6 C14 -8.0(2) 2_666 . . . ? O4 Sm1 O6 C14 -76.8(2) 2_556 . . . ? O1W Sm1 O6 C14 34.8(3) . . . . ? O1 Sm1 O6 C14 152.9(2) . . . . ? O1 Sm1 O6 C14 -138.0(2) 2_656 . . . ? O2 Sm1 O6 C14 -87.1(2) 2_656 . . . ? C1 Sm1 O6 C14 -113.6(2) 2_656 . . . ? Sm1 O2 C1 O1 11.0(3) 2_656 . . . ? Sm1 O2 C1 C2 -170.9(2) 2_656 . . . ? Sm1 O1 C1 O2 -136.6(2) . . . . ? Sm1 O1 C1 O2 -11.4(3) 2_656 . . . ? Sm1 O1 C1 C2 45.3(4) . . . . ? Sm1 O1 C1 C2 170.5(2) 2_656 . . . ? Sm1 O1 C1 Sm1 -125.3(2) . . . 2_656 ? O2 C1 C2 C7 -69.0(4) . . . . ? O1 C1 C2 C7 109.1(3) . . . . ? Sm1 C1 C2 C7 -159.6(13) 2_656 . . . ? O2 C1 C2 C3 107.6(3) . . . . ? O1 C1 C2 C3 -74.3(4) . . . . ? Sm1 C1 C2 C3 17.0(16) 2_656 . . . ? C7 C2 C3 C4 -2.1(4) . . . . ? C1 C2 C3 C4 -178.7(3) . . . . ? C7 C2 C3 C8 176.8(3) . . . . ? C1 C2 C3 C8 0.2(4) . . . . ? C2 C3 C4 C5 -3.1(4) . . . . ? C8 C3 C4 C5 178.0(3) . . . . ? C3 C4 C5 C6 6.1(5) . . . . ? C3 C4 C5 N1 -170.0(3) . . . . ? C13 N1 C5 C4 -147.1(3) . . . . ? C9 N1 C5 C4 35.9(4) . . . . ? C13 N1 C5 C6 36.7(4) . . . . ? C9 N1 C5 C6 -140.2(3) . . . . ? C4 C5 C6 C7 -3.9(5) . . . . ? N1 C5 C6 C7 172.2(3) . . . . ? C5 C6 C7 C2 -1.4(5) . . . . ? C3 C2 C7 C6 4.3(5) . . . . ? C1 C2 C7 C6 -178.9(3) . . . . ? Sm1 O4 C8 O3 2.8(5) 2_556 . . . ? Sm1 O4 C8 C3 -177.52(18) 2_556 . . . ? Sm1 O3 C8 O4 -125.0(3) . . . . ? Sm1 O3 C8 C3 55.4(4) . . . . ? C4 C3 C8 O4 27.7(4) . . . . ? C2 C3 C8 O4 -151.1(3) . . . . ? C4 C3 C8 O3 -152.6(3) . . . . ? C2 C3 C8 O3 28.6(4) . . . . ? C13 N1 C9 C10 -3.2(5) . . . . ? C5 N1 C9 C10 173.8(3) . . . . ? N1 C9 C10 C11 -3.1(6) . . . . ? Sm1 O5 C11 C12 -36.7(5) 2_565 . . . ? Sm1 O5 C11 C10 143.5(3) 2_565 . . . ? C9 C10 C11 O5 -171.5(3) . . . . ? C9 C10 C11 C12 8.7(5) . . . . ? O5 C11 C12 C13 171.8(3) . . . . ? C10 C11 C12 C13 -8.4(5) . . . . ? C9 N1 C13 C12 3.5(5) . . . . ? C5 N1 C13 C12 -173.4(3) . . . . ? C11 C12 C13 N1 2.6(5) . . . . ? Sm1 O6 C14 O7 -172.7(2) . . . . ? Sm1 O6 C14 C14 7.7(4) . . . 2_666 ? Sm1 O7 C14 O6 -172.7(2) 2_666 . . . ? Sm1 O7 C14 C14 7.0(4) 2_666 . . 2_666 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H11 O3 0.837(10) 1.95(2) 2.708(3) 151(4) 2_556 O1W H12 O7 0.836(10) 2.058(18) 2.850(3) 158(3) 1_455 O2W H22 O5 0.838(10) 2.14(2) 2.955(4) 164(6) . _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.669 _refine_diff_density_min -1.349 _refine_diff_density_rms 0.118 _database_code_depnum_ccdc_archive 'CCDC 922526' # Attachment 'Tb.cif' data_a #TrackingRef 'Tb.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H15 N2 O10 Tb' _chemical_formula_weight 674.32 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.648(5) _cell_length_b 10.613(7) _cell_length_c 14.375(9) _cell_angle_alpha 75.779(9) _cell_angle_beta 84.594(10) _cell_angle_gamma 75.893(10) _cell_volume 1096.2(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2814 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 28.12 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.043 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 3.297 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5176 _exptl_absorpt_correction_T_max 0.6553 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5794 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4020 _reflns_number_gt 3622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.2741P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4020 _refine_ls_number_parameters 353 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0901 _refine_ls_wR_factor_gt 0.0783 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Tb1 Tb 0.19563(3) 1.08569(2) 0.337547(16) 0.01621(10) Uani 1 1 d . . . O1 O 0.4210(6) 0.9475(5) 0.2518(3) 0.0434(11) Uani 1 1 d . . . O2 O 0.4325(8) 1.1528(5) 0.1862(3) 0.0645(16) Uani 1 1 d . . . O3 O 0.5532(10) 1.2822(5) 0.0416(4) 0.0679(17) Uani 1 1 d . . . H3 H 0.5312 1.2388 0.0952 0.102 Uiso 1 1 calc R . . O4 O 0.6864(6) 1.2490(4) -0.0919(4) 0.0470(12) Uani 1 1 d . . . O5 O 0.0580(5) 0.8654(4) 0.5676(3) 0.0306(9) Uani 1 1 d . . . O6 O 0.2804(5) 0.8927(3) 0.4588(3) 0.0227(8) Uani 1 1 d . . . O7 O 0.5303(5) 0.8741(3) 0.6069(3) 0.0275(9) Uani 1 1 d . . . O8 O 0.7653(5) 0.7080(4) 0.6363(3) 0.0303(9) Uani 1 1 d . . . O9 O 1.0243(6) 0.2352(4) 0.2170(3) 0.0334(10) Uani 1 1 d . . . O10 O -0.0415(6) 0.0461(4) 0.7065(3) 0.0318(9) Uani 1 1 d . . . C2 C 0.6855(7) 1.0533(5) 0.0283(4) 0.0236(11) Uani 1 1 d . . . C3 C 0.8046(8) 0.9849(6) -0.0305(4) 0.0273(12) Uani 1 1 d . . . H3A H 0.8479 1.0335 -0.0871 0.033 Uiso 1 1 calc R . . C4 C 0.8623(8) 0.8476(6) -0.0091(4) 0.0278(12) Uani 1 1 d . . . H4 H 0.9433 0.8045 -0.0501 0.033 Uiso 1 1 calc R . . C5 C 0.7962(7) 0.7757(5) 0.0750(4) 0.0243(12) Uani 1 1 d . . . C6 C 0.6761(7) 0.8406(5) 0.1347(4) 0.0239(11) Uani 1 1 d . . . H6 H 0.6320 0.7908 0.1905 0.029 Uiso 1 1 calc R . . C7 C 0.4825(8) 1.0288(7) 0.1891(4) 0.0345(15) Uani 1 1 d . . . C8 C 0.6379(9) 1.2024(6) -0.0107(5) 0.0355(14) Uani 1 1 d . . . C9 C 1.0326(8) 0.5730(5) 0.1021(4) 0.0291(13) Uani 1 1 d . . . H9 H 1.1150 0.6250 0.0762 0.035 Uiso 1 1 calc R . . C10 C 1.0952(8) 0.4401(6) 0.1381(4) 0.0329(14) Uani 1 1 d . . . H10 H 1.2186 0.4031 0.1364 0.039 Uiso 1 1 calc R . . C11 C 0.9743(7) 0.3576(5) 0.1783(4) 0.0242(12) Uani 1 1 d . . . C12 C 0.7874(8) 0.4217(5) 0.1712(4) 0.0289(13) Uani 1 1 d . . . H12 H 0.7014 0.3713 0.1921 0.035 Uiso 1 1 calc R . . C13 C 0.7333(8) 0.5549(6) 0.1345(4) 0.0284(12) Uani 1 1 d . . . H13 H 0.6107 0.5943 0.1311 0.034 Uiso 1 1 calc R . . C14 C 0.3147(7) 0.6896(5) 0.5766(4) 0.0181(10) Uani 1 1 d . . . C15 C 0.4936(7) 0.6561(5) 0.6073(4) 0.0178(10) Uani 1 1 d . . . C16 C 0.5757(7) 0.5209(5) 0.6384(4) 0.0252(12) Uani 1 1 d . . . H16 H 0.6939 0.4973 0.6582 0.030 Uiso 1 1 calc R . . C17 C 0.4881(7) 0.4219(5) 0.6406(4) 0.0256(12) Uani 1 1 d . . . H17 H 0.5480 0.3327 0.6587 0.031 Uiso 1 1 calc R . . C18 C 0.3096(7) 0.4561(5) 0.6158(4) 0.0179(10) Uani 1 1 d . . . C19 C 0.2245(6) 0.5888(5) 0.5827(3) 0.0177(10) Uani 1 1 d . . . H19 H 0.1055 0.6107 0.5642 0.021 Uiso 1 1 calc R . . C20 C 0.2109(7) 0.8284(5) 0.5322(3) 0.0164(10) Uani 1 1 d . . . C21 C 0.6005(7) 0.7533(5) 0.6162(4) 0.0203(11) Uani 1 1 d . . . C22 C 0.2899(7) 0.2329(5) 0.6074(4) 0.0209(11) Uani 1 1 d . . . H22 H 0.4042 0.2211 0.5778 0.025 Uiso 1 1 calc R . . C23 C 0.2060(7) 0.1312(5) 0.6281(4) 0.0253(12) Uani 1 1 d . . . H23 H 0.2594 0.0527 0.6087 0.030 Uiso 1 1 calc R . . C24 C 0.0346(7) 0.1424(5) 0.6797(4) 0.0248(12) Uani 1 1 d . . . C25 C -0.0411(7) 0.2690(5) 0.7014(4) 0.0259(12) Uani 1 1 d . . . H25 H -0.1524 0.2828 0.7341 0.031 Uiso 1 1 calc R . . C26 C 0.0465(7) 0.3694(5) 0.6752(4) 0.0238(12) Uani 1 1 d . . . H26 H -0.0069 0.4516 0.6891 0.029 Uiso 1 1 calc R . . C27 C 0.6188(7) 0.9790(5) 0.1135(4) 0.0247(12) Uani 1 1 d . . . N1 N 0.8552(6) 0.6323(4) 0.1023(3) 0.0245(10) Uani 1 1 d . . . N2 N 0.2116(5) 0.3526(4) 0.6287(3) 0.0191(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Tb1 0.01463(15) 0.01088(14) 0.02233(15) -0.00205(10) -0.00003(9) -0.00350(9) O1 0.031(2) 0.064(3) 0.041(3) -0.027(2) 0.014(2) -0.012(2) O2 0.092(4) 0.046(3) 0.036(3) -0.017(2) -0.006(3) 0.029(3) O3 0.113(5) 0.024(2) 0.057(3) -0.010(2) -0.011(3) 0.006(3) O4 0.037(3) 0.025(2) 0.069(3) 0.008(2) -0.001(2) -0.008(2) O5 0.023(2) 0.021(2) 0.038(2) 0.0021(17) 0.0077(17) 0.0015(16) O6 0.0201(19) 0.0137(18) 0.029(2) 0.0016(15) 0.0023(16) -0.0020(15) O7 0.025(2) 0.0146(19) 0.043(2) -0.0048(16) -0.0106(17) -0.0037(16) O8 0.0150(19) 0.0203(19) 0.058(3) -0.0141(19) -0.0072(18) -0.0018(16) O9 0.046(3) 0.0160(19) 0.033(2) 0.0018(17) -0.0146(19) 0.0005(18) O10 0.037(2) 0.019(2) 0.046(2) -0.0068(18) -0.0062(19) -0.0189(18) C2 0.021(3) 0.019(3) 0.031(3) -0.006(2) -0.009(2) -0.001(2) C3 0.025(3) 0.028(3) 0.027(3) 0.003(2) -0.004(2) -0.009(2) C4 0.029(3) 0.024(3) 0.027(3) -0.007(2) 0.002(2) 0.000(2) C5 0.026(3) 0.022(3) 0.024(3) -0.003(2) -0.003(2) -0.004(2) C6 0.024(3) 0.024(3) 0.021(3) -0.004(2) -0.001(2) -0.003(2) C7 0.023(3) 0.045(4) 0.032(3) -0.020(3) -0.012(3) 0.015(3) C8 0.033(3) 0.025(3) 0.049(4) -0.006(3) -0.006(3) -0.010(3) C9 0.026(3) 0.021(3) 0.037(3) -0.003(2) 0.004(2) -0.005(2) C10 0.027(3) 0.024(3) 0.042(4) -0.005(3) -0.007(3) 0.003(3) C11 0.027(3) 0.021(3) 0.021(3) -0.003(2) -0.010(2) 0.003(2) C12 0.033(3) 0.022(3) 0.030(3) -0.001(2) 0.002(3) -0.010(3) C13 0.024(3) 0.028(3) 0.031(3) -0.003(2) 0.001(2) -0.005(2) C14 0.017(2) 0.015(2) 0.021(3) -0.005(2) 0.002(2) -0.002(2) C15 0.015(2) 0.014(2) 0.025(3) -0.004(2) 0.000(2) -0.004(2) C16 0.018(3) 0.016(3) 0.039(3) -0.001(2) -0.010(2) -0.002(2) C17 0.019(3) 0.012(2) 0.043(3) -0.004(2) -0.003(2) 0.000(2) C18 0.017(2) 0.015(2) 0.023(3) -0.005(2) 0.003(2) -0.006(2) C19 0.012(2) 0.017(2) 0.021(3) 0.000(2) -0.0028(19) 0.000(2) C20 0.017(3) 0.012(2) 0.020(3) -0.001(2) -0.004(2) -0.004(2) C21 0.018(3) 0.019(3) 0.024(3) -0.005(2) 0.003(2) -0.006(2) C22 0.022(3) 0.013(2) 0.026(3) -0.005(2) 0.000(2) -0.001(2) C23 0.028(3) 0.015(3) 0.035(3) -0.010(2) -0.002(2) -0.005(2) C24 0.027(3) 0.017(3) 0.032(3) 0.000(2) -0.012(2) -0.010(2) C25 0.013(2) 0.026(3) 0.040(3) -0.009(2) 0.002(2) -0.006(2) C26 0.019(3) 0.015(3) 0.037(3) -0.006(2) 0.001(2) -0.002(2) C27 0.018(3) 0.027(3) 0.028(3) -0.010(2) -0.004(2) 0.001(2) N1 0.028(2) 0.018(2) 0.026(2) -0.0056(19) -0.0004(19) -0.0023(19) N2 0.016(2) 0.016(2) 0.026(2) -0.0038(18) 0.0004(18) -0.0067(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 Tb1 O10 2.264(4) 2_566 ? Tb1 O5 2.291(4) 2_576 ? Tb1 O9 2.302(4) 1_465 ? Tb1 O6 2.338(4) . ? Tb1 O8 2.402(4) 2_676 ? Tb1 O1 2.428(4) . ? Tb1 O7 2.477(4) 2_676 ? Tb1 O2 2.765(6) . ? Tb1 C21 2.801(5) 2_676 ? Tb1 C7 2.972(6) . ? O1 C7 1.230(8) . ? O2 C7 1.269(8) . ? O3 C8 1.287(8) . ? O3 H3 0.8200 . ? O4 C8 1.212(8) . ? O5 C20 1.243(6) . ? O5 Tb1 2.291(4) 2_576 ? O6 C20 1.256(6) . ? O7 C21 1.242(6) . ? O7 Tb1 2.477(4) 2_676 ? O8 C21 1.268(6) . ? O8 Tb1 2.402(4) 2_676 ? O9 C11 1.259(6) . ? O9 Tb1 2.302(4) 1_645 ? O10 C24 1.259(6) . ? O10 Tb1 2.264(4) 2_566 ? C2 C3 1.380(8) . ? C2 C27 1.409(8) . ? C2 C8 1.508(8) . ? C3 C4 1.379(8) . ? C3 H3A 0.9300 . ? C4 C5 1.386(8) . ? C4 H4 0.9300 . ? C5 C6 1.373(8) . ? C5 N1 1.441(7) . ? C6 C27 1.390(8) . ? C6 H6 0.9300 . ? C7 C27 1.533(8) . ? C9 N1 1.349(7) . ? C9 C10 1.358(8) . ? C9 H9 0.9300 . ? C10 C11 1.415(8) . ? C10 H10 0.9300 . ? C11 C12 1.426(7) . ? C12 C13 1.356(8) . ? C12 H12 0.9300 . ? C13 N1 1.365(7) . ? C13 H13 0.9300 . ? C14 C19 1.390(7) . ? C14 C15 1.412(7) . ? C14 C20 1.507(7) . ? C15 C16 1.396(7) . ? C15 C21 1.498(7) . ? C16 C17 1.370(7) . ? C16 H16 0.9300 . ? C17 C18 1.381(7) . ? C17 H17 0.9300 . ? C18 C19 1.383(7) . ? C18 N2 1.442(6) . ? C19 H19 0.9300 . ? C21 Tb1 2.801(5) 2_676 ? C22 C23 1.344(7) . ? C22 N2 1.361(6) . ? C22 H22 0.9300 . ? C23 C24 1.438(8) . ? C23 H23 0.9300 . ? C24 C25 1.425(8) . ? C25 C26 1.352(7) . ? C25 H25 0.9300 . ? C26 N2 1.365(7) . ? C26 H26 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O10 Tb1 O5 83.09(16) 2_566 2_576 ? O10 Tb1 O9 78.59(15) 2_566 1_465 ? O5 Tb1 O9 84.05(15) 2_576 1_465 ? O10 Tb1 O6 80.75(14) 2_566 . ? O5 Tb1 O6 85.64(13) 2_576 . ? O9 Tb1 O6 157.85(14) 1_465 . ? O10 Tb1 O8 154.62(14) 2_566 2_676 ? O5 Tb1 O8 81.39(14) 2_576 2_676 ? O9 Tb1 O8 79.92(14) 1_465 2_676 ? O6 Tb1 O8 117.78(14) . 2_676 ? O10 Tb1 O1 76.11(16) 2_566 . ? O5 Tb1 O1 155.82(16) 2_576 . ? O9 Tb1 O1 103.47(17) 1_465 . ? O6 Tb1 O1 79.03(15) . . ? O8 Tb1 O1 122.32(15) 2_676 . ? O10 Tb1 O7 152.32(14) 2_566 2_676 ? O5 Tb1 O7 114.17(15) 2_576 2_676 ? O9 Tb1 O7 122.82(14) 1_465 2_676 ? O6 Tb1 O7 79.32(13) . 2_676 ? O8 Tb1 O7 53.03(12) 2_676 2_676 ? O1 Tb1 O7 81.38(15) . 2_676 ? O10 Tb1 O2 106.78(17) 2_566 . ? O5 Tb1 O2 152.63(14) 2_576 . ? O9 Tb1 O2 73.40(16) 1_465 . ? O6 Tb1 O2 120.73(14) . . ? O8 Tb1 O2 79.59(15) 2_676 . ? O1 Tb1 O2 48.89(16) . . ? O7 Tb1 O2 68.27(16) 2_676 . ? O10 Tb1 C21 176.92(14) 2_566 2_676 ? O5 Tb1 C21 99.92(15) 2_576 2_676 ? O9 Tb1 C21 101.01(15) 1_465 2_676 ? O6 Tb1 C21 100.05(15) . 2_676 ? O8 Tb1 C21 26.84(14) 2_676 2_676 ? O1 Tb1 C21 101.08(16) . 2_676 ? O7 Tb1 C21 26.31(13) 2_676 2_676 ? O2 Tb1 C21 70.24(16) . 2_676 ? O10 Tb1 C7 90.27(17) 2_566 . ? O5 Tb1 C7 170.53(15) 2_576 . ? O9 Tb1 C7 88.04(16) 1_465 . ? O6 Tb1 C7 100.00(16) . . ? O8 Tb1 C7 102.36(17) 2_676 . ? O1 Tb1 C7 23.70(17) . . ? O7 Tb1 C7 74.58(15) 2_676 . ? O2 Tb1 C7 25.23(16) . . ? C21 Tb1 C7 86.67(17) 2_676 . ? C7 O1 Tb1 103.8(4) . . ? C7 O2 Tb1 86.5(4) . . ? C8 O3 H3 109.5 . . ? C20 O5 Tb1 168.2(4) . 2_576 ? C20 O6 Tb1 138.6(3) . . ? C21 O7 Tb1 91.5(3) . 2_676 ? C21 O8 Tb1 94.4(3) . 2_676 ? C11 O9 Tb1 143.3(4) . 1_645 ? C24 O10 Tb1 146.7(4) . 2_566 ? C3 C2 C27 118.2(5) . . ? C3 C2 C8 113.8(5) . . ? C27 C2 C8 127.9(5) . . ? C2 C3 C4 123.0(5) . . ? C2 C3 H3A 118.5 . . ? C4 C3 H3A 118.5 . . ? C3 C4 C5 118.2(5) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C6 C5 C4 120.3(5) . . ? C6 C5 N1 119.1(5) . . ? C4 C5 N1 120.7(5) . . ? C5 C6 C27 121.6(5) . . ? C5 C6 H6 119.2 . . ? C27 C6 H6 119.2 . . ? O1 C7 O2 120.6(6) . . ? O1 C7 C27 119.3(5) . . ? O2 C7 C27 120.1(6) . . ? O1 C7 Tb1 52.5(3) . . ? O2 C7 Tb1 68.2(4) . . ? C27 C7 Tb1 170.6(5) . . ? O4 C8 O3 119.0(6) . . ? O4 C8 C2 119.5(6) . . ? O3 C8 C2 121.5(6) . . ? N1 C9 C10 122.5(5) . . ? N1 C9 H9 118.8 . . ? C10 C9 H9 118.8 . . ? C9 C10 C11 120.5(5) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? O9 C11 C10 123.5(5) . . ? O9 C11 C12 121.0(5) . . ? C10 C11 C12 115.5(5) . . ? C13 C12 C11 121.0(5) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 N1 121.3(5) . . ? C12 C13 H13 119.3 . . ? N1 C13 H13 119.3 . . ? C19 C14 C15 119.4(4) . . ? C19 C14 C20 115.2(4) . . ? C15 C14 C20 125.4(4) . . ? C16 C15 C14 117.9(4) . . ? C16 C15 C21 116.3(4) . . ? C14 C15 C21 125.6(4) . . ? C17 C16 C15 122.3(5) . . ? C17 C16 H16 118.9 . . ? C15 C16 H16 118.9 . . ? C16 C17 C18 119.3(5) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C19 120.2(4) . . ? C17 C18 N2 119.2(4) . . ? C19 C18 N2 120.6(4) . . ? C18 C19 C14 120.8(5) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? O5 C20 O6 125.6(5) . . ? O5 C20 C14 116.7(4) . . ? O6 C20 C14 117.5(4) . . ? O7 C21 O8 120.5(5) . . ? O7 C21 C15 121.6(5) . . ? O8 C21 C15 117.8(4) . . ? O7 C21 Tb1 62.1(3) . 2_676 ? O8 C21 Tb1 58.8(3) . 2_676 ? C15 C21 Tb1 171.2(4) . 2_676 ? C23 C22 N2 121.7(5) . . ? C23 C22 H22 119.2 . . ? N2 C22 H22 119.2 . . ? C22 C23 C24 120.8(5) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? O10 C24 C25 122.1(5) . . ? O10 C24 C23 122.5(5) . . ? C25 C24 C23 115.4(5) . . ? C26 C25 C24 121.0(5) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 N2 121.4(5) . . ? C25 C26 H26 119.3 . . ? N2 C26 H26 119.3 . . ? C6 C27 C2 118.7(5) . . ? C6 C27 C7 112.4(5) . . ? C2 C27 C7 128.9(5) . . ? C9 N1 C13 118.8(5) . . ? C9 N1 C5 120.5(5) . . ? C13 N1 C5 120.5(5) . . ? C22 N2 C26 119.6(4) . . ? C22 N2 C18 121.3(4) . . ? C26 N2 C18 118.5(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 O10 Tb1 O1 C7 125.1(4) 2_566 . . . ? O5 Tb1 O1 C7 156.5(4) 2_576 . . . ? O9 Tb1 O1 C7 50.7(4) 1_465 . . . ? O6 Tb1 O1 C7 -151.8(4) . . . . ? O8 Tb1 O1 C7 -35.8(4) 2_676 . . . ? O7 Tb1 O1 C7 -71.1(4) 2_676 . . . ? O2 Tb1 O1 C7 -2.5(4) . . . . ? C21 Tb1 O1 C7 -53.6(4) 2_676 . . . ? O10 Tb1 O2 C7 -51.1(4) 2_566 . . . ? O5 Tb1 O2 C7 -159.1(3) 2_576 . . . ? O9 Tb1 O2 C7 -123.3(4) 1_465 . . . ? O6 Tb1 O2 C7 38.0(4) . . . . ? O8 Tb1 O2 C7 154.2(4) 2_676 . . . ? O1 Tb1 O2 C7 2.4(3) . . . . ? O7 Tb1 O2 C7 100.0(4) 2_676 . . . ? C21 Tb1 O2 C7 128.1(4) 2_676 . . . ? O10 Tb1 O6 C20 -70.9(5) 2_566 . . . ? O5 Tb1 O6 C20 12.8(5) 2_576 . . . ? O9 Tb1 O6 C20 -49.6(7) 1_465 . . . ? O8 Tb1 O6 C20 90.7(5) 2_676 . . . ? O1 Tb1 O6 C20 -148.4(5) . . . . ? O7 Tb1 O6 C20 128.4(5) 2_676 . . . ? O2 Tb1 O6 C20 -175.0(5) . . . . ? C21 Tb1 O6 C20 112.1(5) 2_676 . . . ? C7 Tb1 O6 C20 -159.5(5) . . . . ? C27 C2 C3 C4 -0.6(8) . . . . ? C8 C2 C3 C4 -178.5(5) . . . . ? C2 C3 C4 C5 0.4(9) . . . . ? C3 C4 C5 C6 0.2(8) . . . . ? C3 C4 C5 N1 -178.4(5) . . . . ? C4 C5 C6 C27 -0.7(8) . . . . ? N1 C5 C6 C27 178.0(5) . . . . ? Tb1 O1 C7 O2 4.8(7) . . . . ? Tb1 O1 C7 C27 -174.5(4) . . . . ? Tb1 O2 C7 O1 -4.1(6) . . . . ? Tb1 O2 C7 C27 175.2(5) . . . . ? O10 Tb1 C7 O1 -52.6(4) 2_566 . . . ? O5 Tb1 C7 O1 -97.9(10) 2_576 . . . ? O9 Tb1 C7 O1 -131.1(4) 1_465 . . . ? O6 Tb1 C7 O1 28.1(4) . . . . ? O8 Tb1 C7 O1 149.6(4) 2_676 . . . ? O7 Tb1 C7 O1 104.0(4) 2_676 . . . ? O2 Tb1 C7 O1 175.6(6) . . . . ? C21 Tb1 C7 O1 127.7(4) 2_676 . . . ? O10 Tb1 C7 O2 131.9(4) 2_566 . . . ? O5 Tb1 C7 O2 86.5(10) 2_576 . . . ? O9 Tb1 C7 O2 53.3(4) 1_465 . . . ? O6 Tb1 C7 O2 -147.5(4) . . . . ? O8 Tb1 C7 O2 -26.0(4) 2_676 . . . ? O1 Tb1 C7 O2 -175.6(6) . . . . ? O7 Tb1 C7 O2 -71.6(4) 2_676 . . . ? C21 Tb1 C7 O2 -47.9(4) 2_676 . . . ? O10 Tb1 C7 C27 -22(2) 2_566 . . . ? O5 Tb1 C7 C27 -67(3) 2_576 . . . ? O9 Tb1 C7 C27 -100(2) 1_465 . . . ? O6 Tb1 C7 C27 59(2) . . . . ? O8 Tb1 C7 C27 -180(2) 2_676 . . . ? O1 Tb1 C7 C27 31(2) . . . . ? O7 Tb1 C7 C27 135(2) 2_676 . . . ? O2 Tb1 C7 C27 -154(3) . . . . ? C21 Tb1 C7 C27 158(2) 2_676 . . . ? C3 C2 C8 O4 8.6(8) . . . . ? C27 C2 C8 O4 -169.0(6) . . . . ? C3 C2 C8 O3 -168.4(6) . . . . ? C27 C2 C8 O3 14.0(10) . . . . ? N1 C9 C10 C11 -0.2(9) . . . . ? Tb1 O9 C11 C10 57.7(9) 1_645 . . . ? Tb1 O9 C11 C12 -123.2(6) 1_645 . . . ? C9 C10 C11 O9 -176.4(6) . . . . ? C9 C10 C11 C12 4.5(8) . . . . ? O9 C11 C12 C13 176.3(5) . . . . ? C10 C11 C12 C13 -4.6(8) . . . . ? C11 C12 C13 N1 0.5(9) . . . . ? C19 C14 C15 C16 3.1(7) . . . . ? C20 C14 C15 C16 -173.8(5) . . . . ? C19 C14 C15 C21 -172.4(5) . . . . ? C20 C14 C15 C21 10.6(8) . . . . ? C14 C15 C16 C17 -0.7(8) . . . . ? C21 C15 C16 C17 175.3(5) . . . . ? C15 C16 C17 C18 -3.1(9) . . . . ? C16 C17 C18 C19 4.5(8) . . . . ? C16 C17 C18 N2 -172.9(5) . . . . ? C17 C18 C19 C14 -2.0(8) . . . . ? N2 C18 C19 C14 175.3(4) . . . . ? C15 C14 C19 C18 -1.9(8) . . . . ? C20 C14 C19 C18 175.4(5) . . . . ? Tb1 O5 C20 O6 -141.5(15) 2_576 . . . ? Tb1 O5 C20 C14 44(2) 2_576 . . . ? Tb1 O6 C20 O5 -7.8(9) . . . . ? Tb1 O6 C20 C14 166.9(3) . . . . ? C19 C14 C20 O5 53.5(6) . . . . ? C15 C14 C20 O5 -129.4(5) . . . . ? C19 C14 C20 O6 -121.7(5) . . . . ? C15 C14 C20 O6 55.4(7) . . . . ? Tb1 O7 C21 O8 -7.2(5) 2_676 . . . ? Tb1 O7 C21 C15 170.8(4) 2_676 . . . ? Tb1 O8 C21 O7 7.5(5) 2_676 . . . ? Tb1 O8 C21 C15 -170.6(4) 2_676 . . . ? C16 C15 C21 O7 -167.2(5) . . . . ? C14 C15 C21 O7 8.4(8) . . . . ? C16 C15 C21 O8 10.8(7) . . . . ? C14 C15 C21 O8 -173.6(5) . . . . ? C16 C15 C21 Tb1 -54(3) . . . 2_676 ? C14 C15 C21 Tb1 121(2) . . . 2_676 ? N2 C22 C23 C24 -4.3(8) . . . . ? Tb1 O10 C24 C25 108.2(7) 2_566 . . . ? Tb1 O10 C24 C23 -73.9(9) 2_566 . . . ? C22 C23 C24 O10 -174.6(5) . . . . ? C22 C23 C24 C25 3.4(8) . . . . ? O10 C24 C25 C26 177.4(5) . . . . ? C23 C24 C25 C26 -0.7(8) . . . . ? C24 C25 C26 N2 -1.3(9) . . . . ? C5 C6 C27 C2 0.5(8) . . . . ? C5 C6 C27 C7 178.9(5) . . . . ? C3 C2 C27 C6 0.2(8) . . . . ? C8 C2 C27 C6 177.7(5) . . . . ? C3 C2 C27 C7 -178.0(5) . . . . ? C8 C2 C27 C7 -0.5(9) . . . . ? O1 C7 C27 C6 -8.7(8) . . . . ? O2 C7 C27 C6 172.0(5) . . . . ? Tb1 C7 C27 C6 -36(3) . . . . ? O1 C7 C27 C2 169.6(6) . . . . ? O2 C7 C27 C2 -9.7(9) . . . . ? Tb1 C7 C27 C2 142(2) . . . . ? C10 C9 N1 C13 -4.2(9) . . . . ? C10 C9 N1 C5 171.8(5) . . . . ? C12 C13 N1 C9 4.0(8) . . . . ? C12 C13 N1 C5 -172.0(5) . . . . ? C6 C5 N1 C9 -129.1(6) . . . . ? C4 C5 N1 C9 49.5(7) . . . . ? C6 C5 N1 C13 46.8(7) . . . . ? C4 C5 N1 C13 -134.5(6) . . . . ? C23 C22 N2 C26 2.3(8) . . . . ? C23 C22 N2 C18 173.3(5) . . . . ? C25 C26 N2 C22 0.6(8) . . . . ? C25 C26 N2 C18 -170.7(5) . . . . ? C17 C18 N2 C22 -40.6(7) . . . . ? C19 C18 N2 C22 142.1(5) . . . . ? C17 C18 N2 C26 130.6(5) . . . . ? C19 C18 N2 C26 -46.8(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O2 0.82 1.64 2.431(8) 162.7 . _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.609 _refine_diff_density_min -1.081 _refine_diff_density_rms 0.155 _database_code_depnum_ccdc_archive 'CCDC 913858' # Attachment 'Yb.CIF' data_Yb #TrackingRef 'Yb.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H15 N2 O10 Yb' _chemical_formula_weight 688.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.562(4) _cell_length_b 10.499(5) _cell_length_c 14.450(7) _cell_angle_alpha 76.219(8) _cell_angle_beta 84.341(7) _cell_angle_gamma 75.287(7) _cell_volume 1076.8(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.123 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 670 _exptl_absorpt_coefficient_mu 4.415 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.271 _exptl_absorpt_correction_T_max 0.348 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6095 _diffrn_reflns_av_R_equivalents 0.0133 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4305 _reflns_number_gt 4129 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.8800P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4305 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0205 _refine_ls_R_factor_gt 0.0194 _refine_ls_wR_factor_ref 0.0500 _refine_ls_wR_factor_gt 0.0494 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Yb1 Yb 0.192261(15) 0.084638(11) 0.340710(8) 0.01409(5) Uani 1 1 d . . . O1 O 0.4636(3) 0.1210(2) 0.39574(16) 0.0244(5) Uani 1 1 d . . . O2 O 0.2256(3) 0.2899(2) 0.36698(18) 0.0282(5) Uani 1 1 d . . . O3 O 0.7201(3) 0.1049(2) 0.54244(15) 0.0209(4) Uani 1 1 d . . . O4 O 0.9420(3) 0.1314(2) 0.43273(16) 0.0271(5) Uani 1 1 d . . . O5 O 1.0503(3) 0.9512(2) 0.29598(17) 0.0281(5) Uani 1 1 d . . . O6 O 0.0356(4) 0.2301(2) 0.22089(16) 0.0307(5) Uani 1 1 d . . . O7 O -0.5863(3) 0.9817(3) 0.24283(19) 0.0427(7) Uani 1 1 d . . . O8 O -0.5230(5) 1.1782(3) 0.1813(2) 0.0674(11) Uani 1 1 d . . . O9 O -0.4147(7) 1.2933(3) 0.0309(3) 0.0711(12) Uani 1 1 d . . . H9 H -0.478(9) 1.258(6) 0.073(4) 0.085 Uiso 1 1 d . . . O10 O -0.3183(4) 1.2475(3) -0.1046(2) 0.0442(7) Uani 1 1 d . . . N1 N 0.7833(3) 0.6486(2) 0.37047(18) 0.0186(5) Uani 1 1 d . . . N2 N -0.1452(4) 0.6314(3) 0.10698(19) 0.0234(5) Uani 1 1 d . . . C1 C 0.3916(4) 0.2441(3) 0.3867(2) 0.0175(6) Uani 1 1 d . . . C2 C 0.5005(4) 0.3429(3) 0.3946(2) 0.0175(6) Uani 1 1 d . . . C3 C 0.6804(4) 0.3090(3) 0.42481(19) 0.0157(5) Uani 1 1 d . . . C4 C 0.7713(4) 0.4109(3) 0.4182(2) 0.0176(6) Uani 1 1 d . . . H4A H 0.8920 0.3887 0.4363 0.021 Uiso 1 1 calc R . . C5 C 0.6840(4) 0.5449(3) 0.3852(2) 0.0181(6) Uani 1 1 d . . . C6 C 0.5041(4) 0.5805(3) 0.3586(2) 0.0249(7) Uani 1 1 d . . . H6A H 0.4434 0.6706 0.3385 0.030 Uiso 1 1 calc R . . C7 C 0.4172(4) 0.4781(3) 0.3627(3) 0.0262(7) Uani 1 1 d . . . H7A H 0.2974 0.5011 0.3432 0.031 Uiso 1 1 calc R . . C8 C 0.9508(4) 0.6294(3) 0.3244(2) 0.0220(6) Uani 1 1 d . . . H8A H 1.0045 0.5457 0.3106 0.026 Uiso 1 1 calc R . . C9 C 1.0409(4) 0.7296(3) 0.2983(2) 0.0228(6) Uani 1 1 d . . . H9A H 1.1532 0.7143 0.2651 0.027 Uiso 1 1 calc R . . C10 C 0.9662(4) 0.8583(3) 0.3210(2) 0.0189(6) Uani 1 1 d . . . C11 C 0.7929(4) 0.8732(3) 0.3703(2) 0.0226(6) Uani 1 1 d . . . H11A H 0.7382 0.9541 0.3883 0.027 Uiso 1 1 calc R . . C12 C 0.7061(4) 0.7713(3) 0.3915(2) 0.0195(6) Uani 1 1 d . . . H12A H 0.5903 0.7853 0.4214 0.023 Uiso 1 1 calc R . . C13 C 0.7881(4) 0.1685(3) 0.4692(2) 0.0155(5) Uani 1 1 d . . . C14 C -0.0195(5) 0.3550(3) 0.1823(2) 0.0241(7) Uani 1 1 d . . . C15 C -0.2084(5) 0.4190(3) 0.1784(2) 0.0295(7) Uani 1 1 d . . . H15A H -0.2942 0.3682 0.2012 0.035 Uiso 1 1 calc R . . C16 C -0.2660(5) 0.5535(3) 0.1419(2) 0.0288(7) Uani 1 1 d . . . H16A H -0.3908 0.5933 0.1406 0.035 Uiso 1 1 calc R . . C17 C 0.0362(5) 0.5719(3) 0.1040(2) 0.0277(7) Uani 1 1 d . . . H17A H 0.1183 0.6244 0.0768 0.033 Uiso 1 1 calc R . . C18 C 0.1012(5) 0.4374(3) 0.1398(2) 0.0305(7) Uani 1 1 d . . . H18A H 0.2263 0.3994 0.1362 0.037 Uiso 1 1 calc R . . C19 C -0.2050(4) 0.7771(3) 0.0769(2) 0.0233(6) Uani 1 1 d . . . C20 C -0.3238(4) 0.8485(3) 0.1353(2) 0.0233(6) Uani 1 1 d . . . H20A H -0.3700 0.8025 0.1918 0.028 Uiso 1 1 calc R . . C21 C -0.3760(4) 0.9896(3) 0.1106(2) 0.0241(7) Uani 1 1 d . . . C22 C -0.3095(4) 1.0572(3) 0.0233(2) 0.0236(6) Uani 1 1 d . . . C23 C -0.1955(5) 0.9809(3) -0.0349(2) 0.0276(7) Uani 1 1 d . . . H23A H -0.1546 1.0248 -0.0938 0.033 Uiso 1 1 calc R . . C24 C -0.1405(5) 0.8420(3) -0.0086(2) 0.0263(7) Uani 1 1 d . . . H24A H -0.0612 0.7933 -0.0482 0.032 Uiso 1 1 calc R . . C25 C -0.5036(5) 1.0551(4) 0.1829(3) 0.0358(9) Uani 1 1 d . . . C26 C -0.3502(5) 1.2077(4) -0.0211(3) 0.0328(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Yb1 0.01295(7) 0.00861(7) 0.02091(7) -0.00280(5) -0.00011(5) -0.00361(5) O1 0.0239(11) 0.0116(10) 0.0389(12) -0.0053(9) -0.0086(9) -0.0041(9) O2 0.0161(10) 0.0186(11) 0.0538(15) -0.0123(10) -0.0066(10) -0.0053(9) O3 0.0185(10) 0.0149(10) 0.0247(10) 0.0023(8) 0.0021(8) -0.0031(8) O4 0.0196(11) 0.0177(11) 0.0352(12) 0.0000(9) 0.0089(9) 0.0020(9) O5 0.0299(12) 0.0204(11) 0.0392(13) -0.0066(10) -0.0010(10) -0.0154(10) O6 0.0472(15) 0.0160(11) 0.0266(11) -0.0011(9) -0.0114(10) -0.0030(10) O7 0.0238(12) 0.072(2) 0.0387(14) -0.0309(14) 0.0051(11) -0.0081(13) O8 0.106(3) 0.0367(17) 0.0433(17) -0.0196(14) -0.0066(17) 0.0229(18) O9 0.128(4) 0.0213(15) 0.060(2) -0.0125(15) -0.009(2) -0.0053(18) O10 0.0415(15) 0.0264(14) 0.0557(18) 0.0083(12) 0.0014(13) -0.0091(12) N1 0.0168(12) 0.0123(12) 0.0278(13) -0.0040(10) 0.0002(10) -0.0064(10) N2 0.0250(13) 0.0156(13) 0.0277(13) -0.0039(10) -0.0011(11) -0.0022(11) C1 0.0191(14) 0.0143(14) 0.0208(14) -0.0058(11) -0.0005(11) -0.0054(12) C2 0.0140(13) 0.0135(14) 0.0263(15) -0.0046(11) -0.0014(11) -0.0049(11) C3 0.0177(14) 0.0113(13) 0.0177(13) -0.0028(10) 0.0012(11) -0.0041(11) C4 0.0143(13) 0.0138(14) 0.0247(14) -0.0028(11) -0.0016(11) -0.0040(11) C5 0.0187(14) 0.0122(13) 0.0254(15) -0.0063(11) 0.0021(11) -0.0065(11) C6 0.0198(15) 0.0112(14) 0.0421(19) -0.0009(13) -0.0066(13) -0.0036(12) C7 0.0150(14) 0.0150(15) 0.049(2) -0.0059(14) -0.0070(13) -0.0032(12) C8 0.0185(14) 0.0127(14) 0.0350(17) -0.0066(12) -0.0006(12) -0.0031(12) C9 0.0134(13) 0.0177(15) 0.0374(17) -0.0050(13) 0.0014(12) -0.0056(12) C10 0.0193(14) 0.0128(14) 0.0261(15) -0.0037(11) -0.0055(11) -0.0052(12) C11 0.0253(16) 0.0143(14) 0.0297(16) -0.0072(12) -0.0021(13) -0.0049(12) C12 0.0189(14) 0.0138(14) 0.0266(15) -0.0064(12) 0.0016(11) -0.0043(12) C13 0.0172(13) 0.0106(13) 0.0203(13) -0.0032(11) -0.0031(11) -0.0056(11) C14 0.0373(18) 0.0160(15) 0.0186(14) -0.0049(12) -0.0063(13) -0.0026(13) C15 0.0318(18) 0.0258(18) 0.0309(17) -0.0041(14) -0.0032(14) -0.0084(15) C16 0.0253(16) 0.0243(17) 0.0334(17) -0.0022(14) -0.0035(13) -0.0028(14) C17 0.0241(16) 0.0194(16) 0.0381(18) -0.0056(14) 0.0011(14) -0.0042(13) C18 0.0287(17) 0.0198(16) 0.0393(19) -0.0060(14) -0.0029(14) 0.0007(14) C19 0.0257(16) 0.0162(15) 0.0272(15) -0.0049(12) -0.0061(12) -0.0016(13) C20 0.0219(15) 0.0254(16) 0.0208(14) -0.0036(12) -0.0002(12) -0.0040(13) C21 0.0200(15) 0.0243(16) 0.0273(15) -0.0103(13) -0.0054(12) 0.0018(13) C22 0.0216(15) 0.0169(15) 0.0322(16) -0.0040(13) -0.0066(12) -0.0037(12) C23 0.0287(17) 0.0238(17) 0.0279(16) -0.0015(13) 0.0003(13) -0.0066(14) C24 0.0294(17) 0.0221(16) 0.0259(16) -0.0084(13) 0.0021(13) -0.0015(14) C25 0.0264(18) 0.044(2) 0.0313(18) -0.0180(17) -0.0062(15) 0.0123(16) C26 0.0295(18) 0.0204(17) 0.047(2) -0.0055(16) -0.0116(16) -0.0014(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 Yb1 O5 2.205(2) 1_445 ? Yb1 O4 2.221(2) 1_455 ? Yb1 O6 2.227(2) . ? Yb1 O3 2.280(2) 2_656 ? Yb1 O7 2.305(3) 1_645 ? Yb1 O2 2.353(2) . ? Yb1 O1 2.419(2) . ? Yb1 C1 2.744(3) . ? Yb1 C25 3.086(4) 1_645 ? O1 C1 1.249(4) . ? O2 C1 1.260(4) . ? O3 C13 1.249(3) . ? O3 Yb1 2.280(2) 2_656 ? O4 C13 1.237(4) . ? O4 Yb1 2.221(2) 1_655 ? O5 C10 1.261(4) . ? O5 Yb1 2.205(2) 1_665 ? O6 C14 1.274(4) . ? O7 C25 1.247(5) . ? O7 Yb1 2.305(3) 1_465 ? O8 C25 1.257(5) . ? O9 C26 1.280(5) . ? O9 H9 0.81(6) . ? O10 C26 1.201(5) . ? N1 C8 1.362(4) . ? N1 C12 1.365(4) . ? N1 C5 1.438(4) . ? N2 C17 1.357(4) . ? N2 C16 1.360(4) . ? N2 C19 1.451(4) . ? C1 C2 1.508(4) . ? C2 C7 1.384(4) . ? C2 C3 1.402(4) . ? C3 C4 1.392(4) . ? C3 C13 1.514(4) . ? C4 C5 1.383(4) . ? C4 H4A 0.9300 . ? C5 C6 1.384(4) . ? C6 C7 1.383(4) . ? C6 H6A 0.9300 . ? C7 H7A 0.9300 . ? C8 C9 1.356(4) . ? C8 H8A 0.9300 . ? C9 C10 1.427(4) . ? C9 H9A 0.9300 . ? C10 C11 1.419(4) . ? C11 C12 1.353(4) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C14 C18 1.413(5) . ? C14 C15 1.416(5) . ? C15 C16 1.356(5) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C18 1.361(5) . ? C17 H17A 0.9300 . ? C18 H18A 0.9300 . ? C19 C24 1.371(5) . ? C19 C20 1.375(4) . ? C20 C21 1.399(5) . ? C20 H20A 0.9300 . ? C21 C22 1.406(5) . ? C21 C25 1.518(4) . ? C22 C23 1.386(5) . ? C22 C26 1.520(5) . ? C23 C24 1.379(5) . ? C23 H23A 0.9300 . ? C24 H24A 0.9300 . ? C25 Yb1 3.086(4) 1_465 ? 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 Yb1 O4 84.33(9) 1_445 1_455 ? O5 Yb1 O6 79.94(9) 1_445 . ? O4 Yb1 O6 87.02(9) 1_455 . ? O5 Yb1 O3 80.70(9) 1_445 2_656 ? O4 Yb1 O3 85.56(8) 1_455 2_656 ? O6 Yb1 O3 159.85(9) . 2_656 ? O5 Yb1 O7 78.52(10) 1_445 1_645 ? O4 Yb1 O7 162.23(10) 1_455 1_645 ? O6 Yb1 O7 94.48(10) . 1_645 ? O3 Yb1 O7 87.10(10) 2_656 1_645 ? O5 Yb1 O2 155.62(9) 1_445 . ? O4 Yb1 O2 81.52(9) 1_455 . ? O6 Yb1 O2 79.59(9) . . ? O3 Yb1 O2 117.66(9) 2_656 . ? O7 Yb1 O2 116.19(10) 1_645 . ? O5 Yb1 O1 150.08(8) 1_445 . ? O4 Yb1 O1 114.54(9) 1_455 . ? O6 Yb1 O1 122.00(8) . . ? O3 Yb1 O1 78.07(8) 2_656 . ? O7 Yb1 O1 79.58(9) 1_645 . ? O2 Yb1 O1 54.21(7) . . ? O5 Yb1 C1 175.45(8) 1_445 . ? O4 Yb1 C1 100.23(9) 1_455 . ? O6 Yb1 C1 100.20(9) . . ? O3 Yb1 C1 99.55(9) 2_656 . ? O7 Yb1 C1 96.94(10) 1_645 . ? O2 Yb1 C1 27.26(8) . . ? O1 Yb1 C1 27.08(8) . . ? O5 Yb1 C25 93.30(10) 1_445 1_645 ? O4 Yb1 C25 169.43(9) 1_455 1_645 ? O6 Yb1 C25 82.42(10) . 1_645 ? O3 Yb1 C25 104.27(9) 2_656 1_645 ? O7 Yb1 C25 21.01(11) 1_645 1_645 ? O2 Yb1 C25 96.99(10) . 1_645 ? O1 Yb1 C25 72.04(9) . 1_645 ? C1 Yb1 C25 82.23(10) . 1_645 ? C1 O1 Yb1 91.09(17) . . ? C1 O2 Yb1 93.90(18) . . ? C13 O3 Yb1 138.57(19) . 2_656 ? C13 O4 Yb1 168.9(2) . 1_655 ? C10 O5 Yb1 147.3(2) . 1_665 ? C14 O6 Yb1 144.1(2) . . ? C25 O7 Yb1 117.5(3) . 1_465 ? C26 O9 H9 106(5) . . ? C8 N1 C12 118.9(2) . . ? C8 N1 C5 118.9(2) . . ? C12 N1 C5 121.7(2) . . ? C17 N2 C16 119.2(3) . . ? C17 N2 C19 119.2(3) . . ? C16 N2 C19 121.6(3) . . ? O1 C1 O2 120.2(3) . . ? O1 C1 C2 121.7(3) . . ? O2 C1 C2 118.0(3) . . ? O1 C1 Yb1 61.83(15) . . ? O2 C1 Yb1 58.83(15) . . ? C2 C1 Yb1 170.5(2) . . ? C7 C2 C3 118.2(3) . . ? C7 C2 C1 115.9(3) . . ? C3 C2 C1 125.7(3) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 C13 114.8(2) . . ? C2 C3 C13 125.8(3) . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C6 C5 C4 120.6(3) . . ? C6 C5 N1 118.8(3) . . ? C4 C5 N1 120.4(3) . . ? C7 C6 C5 118.1(3) . . ? C7 C6 H6A 121.0 . . ? C5 C6 H6A 121.0 . . ? C6 C7 C2 122.9(3) . . ? C6 C7 H7A 118.5 . . ? C2 C7 H7A 118.5 . . ? C9 C8 N1 121.5(3) . . ? C9 C8 H8A 119.2 . . ? N1 C8 H8A 119.2 . . ? C8 C9 C10 121.1(3) . . ? C8 C9 H9A 119.5 . . ? C10 C9 H9A 119.5 . . ? O5 C10 C11 123.8(3) . . ? O5 C10 C9 120.7(3) . . ? C11 C10 C9 115.5(3) . . ? C12 C11 C10 120.8(3) . . ? C12 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C11 C12 N1 122.0(3) . . ? C11 C12 H12A 119.0 . . ? N1 C12 H12A 119.0 . . ? O4 C13 O3 126.0(3) . . ? O4 C13 C3 116.1(2) . . ? O3 C13 C3 117.7(2) . . ? O6 C14 C18 122.9(3) . . ? O6 C14 C15 121.2(3) . . ? C18 C14 C15 115.9(3) . . ? C16 C15 C14 121.0(3) . . ? C16 C15 H15A 119.5 . . ? C14 C15 H15A 119.5 . . ? C15 C16 N2 121.4(3) . . ? C15 C16 H16A 119.3 . . ? N2 C16 H16A 119.3 . . ? N2 C17 C18 121.6(3) . . ? N2 C17 H17A 119.2 . . ? C18 C17 H17A 119.2 . . ? C17 C18 C14 120.7(3) . . ? C17 C18 H18A 119.7 . . ? C14 C18 H18A 119.7 . . ? C24 C19 C20 120.8(3) . . ? C24 C19 N2 119.7(3) . . ? C20 C19 N2 119.5(3) . . ? C19 C20 C21 120.8(3) . . ? C19 C20 H20A 119.6 . . ? C21 C20 H20A 119.6 . . ? C20 C21 C22 118.8(3) . . ? C20 C21 C25 115.1(3) . . ? C22 C21 C25 126.2(3) . . ? C23 C22 C21 118.4(3) . . ? C23 C22 C26 112.5(3) . . ? C21 C22 C26 129.0(3) . . ? C24 C23 C22 122.3(3) . . ? C24 C23 H23A 118.9 . . ? C22 C23 H23A 118.9 . . ? C19 C24 C23 118.8(3) . . ? C19 C24 H24A 120.6 . . ? C23 C24 H24A 120.6 . . ? O7 C25 O8 122.5(4) . . ? O7 C25 C21 117.0(3) . . ? O8 C25 C21 120.5(4) . . ? O7 C25 Yb1 41.52(18) . 1_465 ? O8 C25 Yb1 81.3(2) . 1_465 ? C21 C25 Yb1 157.7(3) . 1_465 ? O10 C26 O9 119.3(4) . . ? O10 C26 C22 120.5(3) . . ? O9 C26 C22 120.1(3) . . ? 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 Yb1 O1 C1 172.52(17) 1_445 . . . ? O4 Yb1 O1 C1 -62.35(19) 1_455 . . . ? O6 Yb1 O1 C1 40.2(2) . . . . ? O3 Yb1 O1 C1 -141.78(19) 2_656 . . . ? O7 Yb1 O1 C1 129.0(2) 1_645 . . . ? O2 Yb1 O1 C1 -4.28(17) . . . . ? C25 Yb1 O1 C1 108.75(19) 1_645 . . . ? O5 Yb1 O2 C1 -171.88(19) 1_445 . . . ? O4 Yb1 O2 C1 132.9(2) 1_455 . . . ? O6 Yb1 O2 C1 -138.6(2) . . . . ? O3 Yb1 O2 C1 52.5(2) 2_656 . . . ? O7 Yb1 O2 C1 -48.7(2) 1_645 . . . ? O1 Yb1 O2 C1 4.26(17) . . . . ? C25 Yb1 O2 C1 -57.6(2) 1_645 . . . ? O5 Yb1 O6 C14 164.7(4) 1_445 . . . ? O4 Yb1 O6 C14 80.0(4) 1_455 . . . ? O3 Yb1 O6 C14 148.4(3) 2_656 . . . ? O7 Yb1 O6 C14 -117.8(4) 1_645 . . . ? O2 Yb1 O6 C14 -2.0(4) . . . . ? O1 Yb1 O6 C14 -37.3(4) . . . . ? C1 Yb1 O6 C14 -19.9(4) . . . . ? C25 Yb1 O6 C14 -100.6(4) 1_645 . . . ? Yb1 O1 C1 O2 7.5(3) . . . . ? Yb1 O1 C1 C2 -169.8(2) . . . . ? Yb1 O2 C1 O1 -7.8(3) . . . . ? Yb1 O2 C1 C2 169.6(2) . . . . ? O5 Yb1 C1 O1 -54.8(11) 1_445 . . . ? O4 Yb1 C1 O1 125.03(18) 1_455 . . . ? O6 Yb1 C1 O1 -146.19(18) . . . . ? O3 Yb1 C1 O1 37.87(19) 2_656 . . . ? O7 Yb1 C1 O1 -50.34(19) 1_645 . . . ? O2 Yb1 C1 O1 172.4(3) . . . . ? C25 Yb1 C1 O1 -65.39(18) 1_645 . . . ? O5 Yb1 C1 O2 132.8(10) 1_445 . . . ? O4 Yb1 C1 O2 -47.37(19) 1_455 . . . ? O6 Yb1 C1 O2 41.4(2) . . . . ? O3 Yb1 C1 O2 -134.53(18) 2_656 . . . ? O7 Yb1 C1 O2 137.26(19) 1_645 . . . ? O1 Yb1 C1 O2 -172.4(3) . . . . ? C25 Yb1 C1 O2 122.2(2) 1_645 . . . ? O5 Yb1 C1 C2 59.4(18) 1_445 . . . ? O4 Yb1 C1 C2 -120.8(12) 1_455 . . . ? O6 Yb1 C1 C2 -32.0(12) . . . . ? O3 Yb1 C1 C2 152.1(12) 2_656 . . . ? O7 Yb1 C1 C2 63.8(12) 1_645 . . . ? O2 Yb1 C1 C2 -73.4(12) . . . . ? O1 Yb1 C1 C2 114.2(13) . . . . ? C25 Yb1 C1 C2 48.8(12) 1_645 . . . ? O1 C1 C2 C7 166.2(3) . . . . ? O2 C1 C2 C7 -11.1(4) . . . . ? Yb1 C1 C2 C7 57.1(13) . . . . ? O1 C1 C2 C3 -9.2(5) . . . . ? O2 C1 C2 C3 173.4(3) . . . . ? Yb1 C1 C2 C3 -118.3(12) . . . . ? C7 C2 C3 C4 -2.6(4) . . . . ? C1 C2 C3 C4 172.7(3) . . . . ? C7 C2 C3 C13 174.7(3) . . . . ? C1 C2 C3 C13 -9.9(5) . . . . ? C2 C3 C4 C5 2.1(4) . . . . ? C13 C3 C4 C5 -175.5(3) . . . . ? C3 C4 C5 C6 0.4(5) . . . . ? C3 C4 C5 N1 -174.4(3) . . . . ? C8 N1 C5 C6 -129.2(3) . . . . ? C12 N1 C5 C6 43.3(4) . . . . ? C8 N1 C5 C4 45.8(4) . . . . ? C12 N1 C5 C4 -141.8(3) . . . . ? C4 C5 C6 C7 -2.3(5) . . . . ? N1 C5 C6 C7 172.6(3) . . . . ? C5 C6 C7 C2 1.8(5) . . . . ? C3 C2 C7 C6 0.7(5) . . . . ? C1 C2 C7 C6 -175.1(3) . . . . ? C12 N1 C8 C9 -0.7(5) . . . . ? C5 N1 C8 C9 171.9(3) . . . . ? N1 C8 C9 C10 2.1(5) . . . . ? Yb1 O5 C10 C11 66.2(5) 1_665 . . . ? Yb1 O5 C10 C9 -115.4(4) 1_665 . . . ? C8 C9 C10 O5 -179.6(3) . . . . ? C8 C9 C10 C11 -1.1(4) . . . . ? O5 C10 C11 C12 177.1(3) . . . . ? C9 C10 C11 C12 -1.3(4) . . . . ? C10 C11 C12 N1 2.8(5) . . . . ? C8 N1 C12 C11 -1.8(4) . . . . ? C5 N1 C12 C11 -174.2(3) . . . . ? Yb1 O4 C13 O3 145.3(9) 1_655 . . . ? Yb1 O4 C13 C3 -40.0(12) 1_655 . . . ? Yb1 O3 C13 O4 7.1(5) 2_656 . . . ? Yb1 O3 C13 C3 -167.6(2) 2_656 . . . ? C4 C3 C13 O4 -53.9(4) . . . . ? C2 C3 C13 O4 128.6(3) . . . . ? C4 C3 C13 O3 121.2(3) . . . . ? C2 C3 C13 O3 -56.2(4) . . . . ? Yb1 O6 C14 C18 65.2(5) . . . . ? Yb1 O6 C14 C15 -115.8(4) . . . . ? O6 C14 C15 C16 176.4(3) . . . . ? C18 C14 C15 C16 -4.6(5) . . . . ? C14 C15 C16 N2 0.6(5) . . . . ? C17 N2 C16 C15 3.6(5) . . . . ? C19 N2 C16 C15 -173.6(3) . . . . ? C16 N2 C17 C18 -3.7(5) . . . . ? C19 N2 C17 C18 173.6(3) . . . . ? N2 C17 C18 C14 -0.5(5) . . . . ? O6 C14 C18 C17 -176.5(3) . . . . ? C15 C14 C18 C17 4.5(5) . . . . ? C17 N2 C19 C24 49.6(4) . . . . ? C16 N2 C19 C24 -133.2(3) . . . . ? C17 N2 C19 C20 -129.5(3) . . . . ? C16 N2 C19 C20 47.7(4) . . . . ? C24 C19 C20 C21 -2.6(5) . . . . ? N2 C19 C20 C21 176.5(3) . . . . ? C19 C20 C21 C22 2.1(5) . . . . ? C19 C20 C21 C25 -178.4(3) . . . . ? C20 C21 C22 C23 0.3(4) . . . . ? C25 C21 C22 C23 -179.1(3) . . . . ? C20 C21 C22 C26 177.8(3) . . . . ? C25 C21 C22 C26 -1.7(5) . . . . ? C21 C22 C23 C24 -2.3(5) . . . . ? C26 C22 C23 C24 179.9(3) . . . . ? C20 C19 C24 C23 0.7(5) . . . . ? N2 C19 C24 C23 -178.4(3) . . . . ? C22 C23 C24 C19 1.8(5) . . . . ? Yb1 O7 C25 O8 7.7(5) 1_465 . . . ? Yb1 O7 C25 C21 -172.3(2) 1_465 . . . ? C20 C21 C25 O7 -18.0(4) . . . . ? C22 C21 C25 O7 161.5(3) . . . . ? C20 C21 C25 O8 162.0(3) . . . . ? C22 C21 C25 O8 -18.5(5) . . . . ? C20 C21 C25 Yb1 -31.5(7) . . . 1_465 ? C22 C21 C25 Yb1 148.0(5) . . . 1_465 ? C23 C22 C26 O10 15.2(5) . . . . ? C21 C22 C26 O10 -162.4(3) . . . . ? C23 C22 C26 O9 -163.0(4) . . . . ? C21 C22 C26 O9 19.4(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O9 H9 O8 0.81(6) 1.64(6) 2.399(5) 155(7) . _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.013 _refine_diff_density_min -0.849 _refine_diff_density_rms 0.094 _database_code_depnum_ccdc_archive 'CCDC 911666'