# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_1 _database_code_depnum_ccdc_archive 'CCDC 902074' #================================================================ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H21 N4 O14 Sm' _chemical_formula_weight 667.74 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 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 11.241(2) _cell_length_b 9.0060(18) _cell_length_c 23.169(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.80(3) _cell_angle_gamma 90.00 _cell_volume 2337.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 16457 _cell_measurement_theta_min 1.76 _cell_measurement_theta_max 25.50 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.898 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1324 _exptl_absorpt_coefficient_mu 2.593 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6970 _exptl_absorpt_correction_T_max 0.7292 _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 Smart APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16457 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4336 _reflns_number_gt 3935 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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^)+(0.0410P)^2^+0.9508P] 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 4336 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0263 _refine_ls_R_factor_gt 0.0231 _refine_ls_wR_factor_ref 0.0644 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.022 _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 Sm1 Sm 0.202491(12) 0.337852(16) 0.264867(6) 0.01965(7) Uani 1 1 d . . . O1 O 0.2049(2) 0.3771(2) 0.15771(9) 0.0308(5) Uani 1 1 d . . . O2 O 0.10716(19) 0.5383(2) 0.20724(9) 0.0312(5) Uani 1 1 d . . . O3 O 0.0210(2) 0.3542(2) 0.31757(11) 0.0334(5) Uani 1 1 d . . . O4 O 0.12876(19) 0.1511(2) 0.33358(10) 0.0286(5) Uani 1 1 d . . . O5 O 0.3040(2) 0.3604(2) 0.36255(11) 0.0389(6) Uani 1 1 d . . . O6 O 0.24798(19) 0.5738(2) 0.32424(9) 0.0302(5) Uani 1 1 d . . . O7 O 0.4861(3) 0.8609(3) 0.34428(12) 0.0461(7) Uani 1 1 d . . . H7 H 0.5122 0.8703 0.3125 0.069 Uiso 1 1 calc R . . O8 O 0.5190(2) 0.6199(3) 0.32817(10) 0.0355(5) Uani 1 1 d . . . O9 O 0.3975(2) 0.4324(3) 0.24671(12) 0.0550(8) Uani 1 1 d . . . H9B H 0.3973 0.5265 0.2491 0.082 Uiso 1 1 d R . . H9C H 0.4494 0.3972 0.2718 0.082 Uiso 1 1 d R . . O10 O 0.3177(2) 0.1196(3) 0.24951(11) 0.0360(5) Uani 1 1 d . . . H10A H 0.2872 0.0739 0.2197 0.054 Uiso 1 1 d R . . H10C H 0.3889 0.1445 0.2443 0.054 Uiso 1 1 d R . . O11 O 0.0467(2) 0.1750(3) 0.21288(11) 0.0385(6) Uani 1 1 d . . . H11A H 0.0653 0.1589 0.1786 0.058 Uiso 1 1 d R . . H11B H 0.0433 0.0929 0.2308 0.058 Uiso 1 1 d R . . N1 N 0.3350(2) 0.5978(3) 0.57761(11) 0.0321(6) Uani 1 1 d . . . H1A H 0.2844 0.5388 0.5915 0.039 Uiso 1 1 calc R . . N2 N 0.4711(2) 0.7699(3) 0.57329(11) 0.0339(6) Uani 1 1 d . . . N3 N 0.1670(2) 0.6129(3) -0.05018(11) 0.0311(6) Uani 1 1 d . . . H3A H 0.2168 0.5509 -0.0629 0.037 Uiso 1 1 calc R . . N4 N 0.0360(2) 0.8004(3) -0.05064(12) 0.0339(6) Uani 1 1 d . . . C1 C 0.1068(3) 0.7194(4) -0.08104(14) 0.0358(8) Uani 1 1 d . . . H1B H 0.1142 0.7349 -0.1203 0.043 Uiso 1 1 calc R . . C2 C 0.1337(3) 0.6222(4) 0.00580(13) 0.0254(7) Uani 1 1 d . . . C3 C 0.1641(3) 0.5404(3) 0.05542(13) 0.0265(7) Uani 1 1 d . . . H3B H 0.2195 0.4637 0.0555 0.032 Uiso 1 1 calc R . . C4 C 0.1091(3) 0.5769(3) 0.10508(13) 0.0245(6) Uani 1 1 d . . . C5 C 0.0260(3) 0.6961(3) 0.10410(13) 0.0251(6) Uani 1 1 d . . . C6 C -0.0009(3) 0.7786(4) 0.05466(13) 0.0291(7) Uani 1 1 d . . . H6A H -0.0531 0.8586 0.0548 0.035 Uiso 1 1 calc R . . C7 C 0.0514(3) 0.7399(4) 0.00462(13) 0.0267(7) Uani 1 1 d . . . C8 C 0.1417(3) 0.4926(3) 0.15958(12) 0.0235(6) Uani 1 1 d . . . C9 C 0.0443(3) 0.2340(4) 0.34532(13) 0.0265(7) Uani 1 1 d . . . C10 C 0.4047(3) 0.6932(4) 0.60772(15) 0.0370(8) Uani 1 1 d . . . H10B H 0.4071 0.7051 0.6477 0.044 Uiso 1 1 calc R . . C11 C 0.3573(3) 0.6093(4) 0.51997(14) 0.0265(7) Uani 1 1 d . . . C12 C 0.3117(3) 0.5333(3) 0.47077(13) 0.0266(7) Uani 1 1 d . . . H12A H 0.2556 0.4581 0.4730 0.032 Uiso 1 1 calc R . . C13 C 0.3529(2) 0.5738(3) 0.41858(13) 0.0238(6) Uani 1 1 d . . . C14 C 0.4382(3) 0.6890(3) 0.41526(13) 0.0230(6) Uani 1 1 d . . . C15 C 0.4840(3) 0.7617(3) 0.46439(13) 0.0278(7) Uani 1 1 d . . . H15A H 0.5408 0.8363 0.4625 0.033 Uiso 1 1 calc R . . C16 C 0.4430(3) 0.7202(4) 0.51667(13) 0.0263(7) Uani 1 1 d . . . C17 C 0.2990(2) 0.4993(3) 0.36452(13) 0.0249(6) Uani 1 1 d . . . C18 C 0.4842(3) 0.7256(4) 0.35749(14) 0.0276(7) Uani 1 1 d . . . OW1 O 0.1752(3) 0.1017(3) 0.10655(13) 0.0618(8) Uani 1 1 d . . . HW1A H 0.1598 0.1620 0.0787 0.093 Uiso 1 1 d R . . HW1C H 0.1194 0.0381 0.1069 0.093 Uiso 1 1 d R . . OW2 O 0.34416(19) 0.0463(2) 0.39586(9) 0.0332(5) Uani 1 1 d . . . HW2A H 0.4042 0.0173 0.3789 0.050 Uiso 1 1 d R . . HW2C H 0.2862 0.0634 0.3708 0.050 Uiso 1 1 d R . . OW3 O 0.2436(4) -0.1648(3) 0.23512(19) 0.0847(12) Uani 1 1 d . . . HW3A H 0.2588 -0.2081 0.2675 0.127 Uiso 1 1 d R . . HW3B H 0.1792 -0.1992 0.2185 0.127 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 Sm1 0.02255(10) 0.02093(10) 0.01605(10) 0.00106(6) 0.00504(6) 0.00085(5) O1 0.0452(13) 0.0268(12) 0.0215(12) 0.0033(9) 0.0084(10) 0.0105(10) O2 0.0403(12) 0.0348(13) 0.0192(11) 0.0033(10) 0.0073(9) 0.0114(10) O3 0.0365(13) 0.0308(13) 0.0347(14) 0.0068(10) 0.0134(10) 0.0063(9) O4 0.0267(11) 0.0337(13) 0.0264(12) 0.0041(9) 0.0079(9) 0.0023(9) O5 0.0567(16) 0.0266(13) 0.0312(14) 0.0000(10) -0.0098(12) -0.0041(11) O6 0.0382(12) 0.0278(12) 0.0240(12) -0.0016(10) -0.0006(9) 0.0039(10) O7 0.0644(17) 0.0395(16) 0.0392(15) 0.0105(12) 0.0326(13) 0.0060(12) O8 0.0409(13) 0.0353(13) 0.0326(13) -0.0071(11) 0.0179(11) -0.0038(11) O9 0.0471(15) 0.0653(19) 0.0563(18) -0.0318(15) 0.0272(13) -0.0258(13) O10 0.0358(12) 0.0308(13) 0.0435(14) -0.0024(11) 0.0157(11) 0.0035(10) O11 0.0465(14) 0.0428(15) 0.0267(13) -0.0015(10) 0.0058(11) -0.0105(11) N1 0.0402(15) 0.0366(16) 0.0204(14) 0.0031(12) 0.0070(11) -0.0073(13) N2 0.0402(15) 0.0381(17) 0.0233(15) -0.0047(13) 0.0010(11) -0.0052(13) N3 0.0377(15) 0.0341(15) 0.0231(14) 0.0022(12) 0.0116(12) 0.0054(12) N4 0.0388(15) 0.0411(16) 0.0225(15) 0.0084(13) 0.0065(12) 0.0063(13) C1 0.0424(19) 0.046(2) 0.0197(17) 0.0064(16) 0.0067(14) 0.0005(16) C2 0.0277(15) 0.0285(17) 0.0209(16) 0.0011(13) 0.0072(12) -0.0009(12) C3 0.0309(15) 0.0246(16) 0.0249(16) 0.0025(13) 0.0065(12) 0.0054(12) C4 0.0276(15) 0.0277(17) 0.0185(15) 0.0029(13) 0.0045(12) 0.0011(12) C5 0.0274(15) 0.0256(16) 0.0228(17) 0.0014(13) 0.0062(12) 0.0013(12) C6 0.0314(16) 0.0313(18) 0.0253(17) 0.0043(14) 0.0064(13) 0.0086(14) C7 0.0286(15) 0.0305(18) 0.0217(16) 0.0076(13) 0.0050(12) 0.0041(13) C8 0.0287(14) 0.0216(16) 0.0207(15) 0.0005(13) 0.0047(12) -0.0012(12) C9 0.0268(15) 0.0325(18) 0.0206(16) -0.0037(14) 0.0041(12) -0.0048(13) C10 0.051(2) 0.039(2) 0.0209(18) 0.0007(15) 0.0018(15) -0.0040(16) C11 0.0273(15) 0.0259(16) 0.0265(17) 0.0024(14) 0.0042(13) -0.0013(13) C12 0.0295(15) 0.0276(17) 0.0226(16) 0.0031(13) 0.0021(12) -0.0071(13) C13 0.0240(14) 0.0246(16) 0.0226(16) -0.0007(13) 0.0012(12) -0.0010(12) C14 0.0244(14) 0.0233(16) 0.0218(16) 0.0034(12) 0.0049(12) 0.0009(12) C15 0.0276(15) 0.0265(17) 0.0297(18) 0.0006(14) 0.0051(13) -0.0050(13) C16 0.0281(15) 0.0290(17) 0.0214(16) 0.0009(14) -0.0002(12) -0.0018(13) C17 0.0259(14) 0.0296(18) 0.0202(15) -0.0014(13) 0.0074(12) -0.0023(13) C18 0.0247(15) 0.0328(19) 0.0259(17) 0.0024(15) 0.0059(12) -0.0010(13) OW1 0.0588(17) 0.0568(18) 0.066(2) -0.0221(16) -0.0159(15) 0.0215(15) OW2 0.0346(11) 0.0316(13) 0.0336(13) 0.0057(10) 0.0033(10) 0.0021(10) OW3 0.087(3) 0.046(2) 0.117(3) 0.0088(18) -0.013(2) -0.0255(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sm1 O10 2.397(2) . ? Sm1 O9 2.421(2) . ? Sm1 O2 2.439(2) . ? Sm1 O5 2.456(2) . ? Sm1 O3 2.468(2) . ? Sm1 O4 2.504(2) . ? Sm1 O1 2.510(2) . ? Sm1 O11 2.513(2) . ? Sm1 O6 2.559(2) . ? Sm1 C9 2.840(3) . ? Sm1 C8 2.842(3) . ? Sm1 C17 2.864(3) . ? O1 C8 1.262(4) . ? O2 C8 1.269(4) . ? O3 C9 1.275(4) . ? O4 C9 1.256(4) . ? O5 C17 1.254(4) . ? O6 C17 1.249(4) . ? O7 C18 1.257(4) . ? O7 H7 0.8200 . ? O8 C18 1.251(4) . ? O9 H9B 0.8498 . ? O9 H9C 0.8498 . ? O10 H10A 0.8500 . ? O10 H10C 0.8500 . ? O11 H11A 0.8500 . ? O11 H11B 0.8500 . ? N1 C10 1.322(4) . ? N1 C11 1.383(4) . ? N1 H1A 0.8600 . ? N2 C10 1.331(4) . ? N2 C16 1.397(4) . ? N3 C1 1.345(4) . ? N3 C2 1.382(4) . ? N3 H3A 0.8600 . ? N4 C1 1.325(4) . ? N4 C7 1.389(4) . ? C1 H1B 0.9300 . ? C2 C3 1.384(4) . ? C2 C7 1.405(4) . ? C3 C4 1.391(4) . ? C3 H3B 0.9300 . ? C4 C5 1.422(4) . ? C4 C8 1.493(4) . ? C5 C6 1.377(4) . ? C5 C9 1.506(4) 2 ? C6 C7 1.387(4) . ? C6 H6A 0.9300 . ? C9 C5 1.506(4) 2_545 ? C10 H10B 0.9300 . ? C11 C12 1.390(4) . ? C11 C16 1.394(4) . ? C12 C13 1.380(4) . ? C12 H12A 0.9300 . ? C13 C14 1.419(4) . ? C13 C17 1.503(4) . ? C14 C15 1.375(4) . ? C14 C18 1.511(4) . ? C15 C16 1.383(4) . ? C15 H15A 0.9300 . ? OW1 HW1A 0.8497 . ? OW1 HW1C 0.8501 . ? OW2 HW2A 0.8499 . ? OW2 HW2C 0.8501 . ? OW3 HW3A 0.8501 . ? OW3 HW3B 0.8500 . ? 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 Sm1 O9 75.78(9) . . ? O10 Sm1 O2 138.05(8) . . ? O9 Sm1 O2 90.42(9) . . ? O10 Sm1 O5 89.39(8) . . ? O9 Sm1 O5 76.90(9) . . ? O2 Sm1 O5 126.31(7) . . ? O10 Sm1 O3 126.99(7) . . ? O9 Sm1 O3 149.64(8) . . ? O2 Sm1 O3 83.29(7) . . ? O5 Sm1 O3 83.04(9) . . ? O10 Sm1 O4 75.83(8) . . ? O9 Sm1 O4 134.37(9) . . ? O2 Sm1 O4 133.74(7) . . ? O5 Sm1 O4 67.83(8) . . ? O3 Sm1 O4 52.73(7) . . ? O10 Sm1 O1 85.29(8) . . ? O9 Sm1 O1 72.17(9) . . ? O2 Sm1 O1 52.78(7) . . ? O5 Sm1 O1 148.99(9) . . ? O3 Sm1 O1 123.97(8) . . ? O4 Sm1 O1 139.01(8) . . ? O10 Sm1 O11 79.25(8) . . ? O9 Sm1 O11 136.60(8) . . ? O2 Sm1 O11 85.02(8) . . ? O5 Sm1 O11 137.83(8) . . ? O3 Sm1 O11 72.57(8) . . ? O4 Sm1 O11 70.02(8) . . ? O1 Sm1 O11 70.90(8) . . ? O10 Sm1 O6 132.42(8) . . ? O9 Sm1 O6 70.03(8) . . ? O2 Sm1 O6 74.86(7) . . ? O5 Sm1 O6 51.66(7) . . ? O3 Sm1 O6 79.67(7) . . ? O4 Sm1 O6 106.12(7) . . ? O1 Sm1 O6 113.37(7) . . ? O11 Sm1 O6 147.36(7) . . ? O10 Sm1 C9 101.73(9) . . ? O9 Sm1 C9 148.83(9) . . ? O2 Sm1 C9 109.41(8) . . ? O5 Sm1 C9 71.98(9) . . ? O3 Sm1 C9 26.63(8) . . ? O4 Sm1 C9 26.23(8) . . ? O1 Sm1 C9 138.99(8) . . ? O11 Sm1 C9 70.91(8) . . ? O6 Sm1 C9 91.63(8) . . ? O10 Sm1 C8 111.63(9) . . ? O9 Sm1 C8 80.48(10) . . ? O2 Sm1 C8 26.43(8) . . ? O5 Sm1 C8 144.10(8) . . ? O3 Sm1 C8 104.24(8) . . ? O4 Sm1 C8 143.73(8) . . ? O1 Sm1 C8 26.35(7) . . ? O11 Sm1 C8 76.53(8) . . ? O6 Sm1 C8 94.43(8) . . ? C9 Sm1 C8 127.29(9) . . ? O10 Sm1 C17 111.29(9) . . ? O9 Sm1 C17 70.98(8) . . ? O2 Sm1 C17 100.66(8) . . ? O5 Sm1 C17 25.82(8) . . ? O3 Sm1 C17 81.02(8) . . ? O4 Sm1 C17 87.23(8) . . ? O1 Sm1 C17 133.72(8) . . ? O11 Sm1 C17 152.19(8) . . ? O6 Sm1 C17 25.85(8) . . ? C9 Sm1 C17 81.60(8) . . ? C8 Sm1 C17 119.38(9) . . ? C8 O1 Sm1 91.68(17) . . ? C8 O2 Sm1 94.79(17) . . ? C9 O3 Sm1 93.18(17) . . ? C9 O4 Sm1 91.99(18) . . ? C17 O5 Sm1 95.57(19) . . ? C17 O6 Sm1 90.84(18) . . ? C18 O7 H7 109.5 . . ? Sm1 O9 H9B 109.4 . . ? Sm1 O9 H9C 109.2 . . ? H9B O9 H9C 109.5 . . ? Sm1 O10 H10A 109.3 . . ? Sm1 O10 H10C 109.3 . . ? H10A O10 H10C 109.5 . . ? Sm1 O11 H11A 109.3 . . ? Sm1 O11 H11B 109.3 . . ? H11A O11 H11B 109.5 . . ? C10 N1 C11 108.3(3) . . ? C10 N1 H1A 125.9 . . ? C11 N1 H1A 125.9 . . ? C10 N2 C16 107.6(3) . . ? C1 N3 C2 107.0(3) . . ? C1 N3 H3A 126.5 . . ? C2 N3 H3A 126.5 . . ? C1 N4 C7 103.9(3) . . ? N4 C1 N3 114.1(3) . . ? N4 C1 H1B 123.0 . . ? N3 C1 H1B 123.0 . . ? N3 C2 C3 132.8(3) . . ? N3 C2 C7 104.9(3) . . ? C3 C2 C7 122.3(3) . . ? C2 C3 C4 117.7(3) . . ? C2 C3 H3B 121.1 . . ? C4 C3 H3B 121.1 . . ? C3 C4 C5 120.2(3) . . ? C3 C4 C8 119.0(3) . . ? C5 C4 C8 120.8(3) . . ? C6 C5 C4 121.2(3) . . ? C6 C5 C9 115.6(3) . 2 ? C4 C5 C9 123.0(3) . 2 ? C5 C6 C7 118.7(3) . . ? C5 C6 H6A 120.6 . . ? C7 C6 H6A 120.6 . . ? C6 C7 N4 130.0(3) . . ? C6 C7 C2 119.8(3) . . ? N4 C7 C2 110.2(3) . . ? O1 C8 O2 120.8(3) . . ? O1 C8 C4 119.3(3) . . ? O2 C8 C4 119.9(3) . . ? O1 C8 Sm1 61.97(15) . . ? O2 C8 Sm1 58.79(15) . . ? C4 C8 Sm1 178.7(2) . . ? O4 C9 O3 121.5(3) . . ? O4 C9 C5 119.3(3) . 2_545 ? O3 C9 C5 119.1(3) . 2_545 ? O4 C9 Sm1 61.78(16) . . ? O3 C9 Sm1 60.19(15) . . ? C5 C9 Sm1 169.5(2) 2_545 . ? N1 C10 N2 111.0(3) . . ? N1 C10 H10B 124.5 . . ? N2 C10 H10B 124.5 . . ? N1 C11 C12 132.1(3) . . ? N1 C11 C16 106.8(3) . . ? C12 C11 C16 121.1(3) . . ? C13 C12 C11 117.4(3) . . ? C13 C12 H12A 121.3 . . ? C11 C12 H12A 121.3 . . ? C12 C13 C14 121.2(3) . . ? C12 C13 C17 118.1(3) . . ? C14 C13 C17 120.5(3) . . ? C15 C14 C13 120.7(3) . . ? C15 C14 C18 119.8(3) . . ? C13 C14 C18 119.4(3) . . ? C14 C15 C16 117.8(3) . . ? C14 C15 H15A 121.1 . . ? C16 C15 H15A 121.1 . . ? C15 C16 C11 121.6(3) . . ? C15 C16 N2 132.1(3) . . ? C11 C16 N2 106.3(3) . . ? O6 C17 O5 121.9(3) . . ? O6 C17 C13 120.7(3) . . ? O5 C17 C13 117.3(3) . . ? O6 C17 Sm1 63.31(16) . . ? O5 C17 Sm1 58.60(16) . . ? C13 C17 Sm1 175.9(2) . . ? O8 C18 O7 126.3(3) . . ? O8 C18 C14 117.4(3) . . ? O7 C18 C14 116.2(3) . . ? HW1A OW1 HW1C 109.5 . . ? HW2A OW2 HW2C 109.5 . . ? HW3A OW3 HW3B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.653 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.084 data_2 _database_code_depnum_ccdc_archive 'CCDC 902075' #================================================================ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H21 Gd N4 O14' _chemical_formula_weight 674.64 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' 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 '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 11.227(2) _cell_length_b 8.9820(18) _cell_length_c 23.119(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.84(3) _cell_angle_gamma 90.00 _cell_volume 2323.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 22175 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.929 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1332 _exptl_absorpt_coefficient_mu 2.936 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5000 _exptl_absorpt_correction_T_max 0.7558 _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 Smart APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 22175 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5323 _reflns_number_gt 4720 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5323 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0320 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 0.797 _refine_ls_restrained_S_all 0.797 _refine_ls_shift/su_max 0.015 _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 Gd1 Gd 0.202119(12) 0.161742(15) 0.264910(6) 0.01780(8) Uani 1 1 d . . . O1 O 0.1062(2) -0.0371(3) 0.20804(10) 0.0287(5) Uani 1 1 d . . . O2 O 0.2046(2) 0.1245(3) 0.15841(10) 0.0281(5) Uani 1 1 d . . . O3 O 0.0222(2) 0.1452(3) 0.31770(12) 0.0293(6) Uani 1 1 d . . . O4 O 0.1296(2) 0.3489(3) 0.33297(11) 0.0258(5) Uani 1 1 d . . . O5 O 0.2466(2) -0.0743(3) 0.32390(10) 0.0290(5) Uani 1 1 d . . . O6 O 0.3056(3) 0.1406(3) 0.36125(12) 0.0365(6) Uani 1 1 d . . . O7 O 0.4879(3) -0.3615(3) 0.34401(14) 0.0434(8) Uani 1 1 d . . . O8 O 0.5180(2) -0.1197(3) 0.32789(12) 0.0342(6) Uani 1 1 d . . . H8 H 0.5408 -0.1505 0.2973 0.051 Uiso 1 1 calc R . . O9 O 0.3941(3) 0.0641(4) 0.24669(14) 0.0523(9) Uani 1 1 d . . . H9A H 0.4104 0.0893 0.2128 0.078 Uiso 1 1 d R . . H9B H 0.4469 0.0991 0.2715 0.078 Uiso 1 1 d R . . O10 O 0.3169(2) 0.3765(3) 0.24921(13) 0.0320(5) Uani 1 1 d . . . H10A H 0.2864 0.4224 0.2194 0.048 Uiso 1 1 d R . . H10C H 0.3172 0.4332 0.2787 0.048 Uiso 1 1 d R . . O11 O 0.0488(3) 0.3235(3) 0.21274(12) 0.0335(6) Uani 1 1 d . . . H11B H -0.0188 0.2805 0.2114 0.050 Uiso 1 1 d R . . H11C H 0.0451 0.4058 0.2307 0.050 Uiso 1 1 d R . . N1 N 0.0364(3) -0.2997(4) -0.05036(13) 0.0319(6) Uani 1 1 d . . . H1A H -0.0088 -0.3727 -0.0623 0.038 Uiso 1 1 calc R . . N2 N 0.1680(3) -0.1123(4) -0.04993(12) 0.0286(6) Uani 1 1 d . . . N3 N 0.3336(3) -0.0961(4) 0.57751(12) 0.0301(6) Uani 1 1 d . . . N4 N 0.4699(3) -0.2682(4) 0.57307(12) 0.0301(6) Uani 1 1 d . . . H4A H 0.5208 -0.3366 0.5837 0.036 Uiso 1 1 calc R . . C1 C 0.1072(3) -0.2187(5) -0.08072(15) 0.0318(7) Uani 1 1 d . . . H1B H 0.1143 -0.2341 -0.1201 0.038 Uiso 1 1 calc R . . C2 C 0.0515(3) -0.2406(4) 0.00492(14) 0.0254(6) Uani 1 1 d . . . C3 C -0.0011(3) -0.2799(4) 0.05488(15) 0.0283(7) Uani 1 1 d . . . H3B H -0.0532 -0.3604 0.0550 0.034 Uiso 1 1 calc R . . C4 C 0.0260(3) -0.1964(4) 0.10466(14) 0.0228(6) Uani 1 1 d . . . C5 C 0.1088(3) -0.0772(4) 0.10572(13) 0.0225(6) Uani 1 1 d . . . C6 C 0.1635(3) -0.0395(4) 0.05610(14) 0.0247(6) Uani 1 1 d . . . H6A H 0.2179 0.0386 0.0562 0.030 Uiso 1 1 calc R . . C7 C 0.1342(3) -0.1224(4) 0.00621(13) 0.0224(6) Uani 1 1 d . . . C8 C 0.1417(3) 0.0081(4) 0.16011(14) 0.0228(6) Uani 1 1 d . . . C9 C 0.0440(3) 0.2648(4) 0.34459(13) 0.0218(6) Uani 1 1 d . . . C10 C 0.4045(4) -0.1927(5) 0.60792(16) 0.0350(8) Uani 1 1 d . . . H10B H 0.4074 -0.2051 0.6479 0.042 Uiso 1 1 calc R . . C11 C 0.3567(3) -0.1093(4) 0.51927(14) 0.0235(6) Uani 1 1 d . . . C12 C 0.3115(3) -0.0320(4) 0.47043(14) 0.0257(6) Uani 1 1 d . . . H12A H 0.2562 0.0445 0.4727 0.031 Uiso 1 1 calc R . . C13 C 0.3524(3) -0.0740(4) 0.41815(13) 0.0219(6) Uani 1 1 d . . . C14 C 0.4392(3) -0.1880(4) 0.41522(14) 0.0232(6) Uani 1 1 d . . . C15 C 0.4850(3) -0.2620(4) 0.46445(14) 0.0254(6) Uani 1 1 d . . . H15A H 0.5415 -0.3372 0.4626 0.030 Uiso 1 1 calc R . . C16 C 0.4434(3) -0.2196(4) 0.51700(14) 0.0242(6) Uani 1 1 d . . . C17 C 0.2985(3) 0.0015(4) 0.36411(14) 0.0235(6) Uani 1 1 d . . . C18 C 0.4843(3) -0.2269(4) 0.35684(14) 0.0235(6) Uani 1 1 d . . . OW1 O 0.1730(3) 0.1017(4) 0.60651(16) 0.0587(10) Uani 1 1 d . . . HW1A H 0.2347 0.0491 0.6024 0.088 Uiso 1 1 d R . . HW1C H 0.1605 0.1054 0.6422 0.088 Uiso 1 1 d R . . OW2 O 0.3450(2) 0.4529(3) 0.39520(11) 0.0307(5) Uani 1 1 d . . . HW2B H 0.2863 0.4361 0.3704 0.046 Uiso 1 1 d R . . HW2C H 0.3263 0.5206 0.4184 0.046 Uiso 1 1 d R . . OW3 O 0.2402(5) 0.6624(4) 0.2352(2) 0.0743(13) Uani 1 1 d . . . HW3A H 0.2552 0.7059 0.2677 0.111 Uiso 1 1 d R . . HW3B H 0.2971 0.6778 0.2139 0.111 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 Gd1 0.01986(11) 0.01957(11) 0.01439(11) -0.00102(5) 0.00393(7) -0.00100(5) O1 0.0367(13) 0.0328(13) 0.0173(10) -0.0037(9) 0.0063(10) -0.0105(10) O2 0.0397(13) 0.0235(11) 0.0216(11) -0.0031(9) 0.0046(10) -0.0112(10) O3 0.0324(13) 0.0292(13) 0.0276(13) -0.0054(10) 0.0100(11) -0.0074(9) O4 0.0242(12) 0.0310(13) 0.0230(12) -0.0044(9) 0.0072(10) -0.0024(8) O5 0.0373(13) 0.0273(12) 0.0219(11) 0.0018(9) -0.0008(10) -0.0045(10) O6 0.0532(17) 0.0263(13) 0.0271(13) -0.0010(10) -0.0138(12) 0.0037(11) O7 0.062(2) 0.0330(14) 0.0388(16) -0.0083(12) 0.0268(15) -0.0031(13) O8 0.0391(14) 0.0356(14) 0.0305(13) 0.0061(12) 0.0182(12) 0.0053(12) O9 0.0442(16) 0.071(2) 0.0456(16) 0.0353(16) 0.0263(14) 0.0277(15) O10 0.0340(13) 0.0288(13) 0.0353(13) 0.0000(12) 0.0156(11) -0.0028(11) O11 0.0359(14) 0.0374(15) 0.0277(13) 0.0016(10) 0.0066(11) 0.0086(10) N1 0.0356(16) 0.0390(17) 0.0217(14) -0.0101(13) 0.0048(12) -0.0098(13) N2 0.0353(16) 0.0338(16) 0.0176(13) -0.0015(12) 0.0071(11) 0.0003(13) N3 0.0392(16) 0.0361(17) 0.0156(12) -0.0009(12) 0.0058(11) 0.0027(13) N4 0.0369(15) 0.0330(16) 0.0198(13) 0.0034(12) -0.0008(11) 0.0045(12) C1 0.0365(18) 0.041(2) 0.0183(15) -0.0061(15) 0.0053(14) -0.0001(16) C2 0.0271(15) 0.0270(16) 0.0224(15) -0.0053(13) 0.0052(12) -0.0023(13) C3 0.0305(16) 0.0318(18) 0.0231(15) -0.0023(14) 0.0051(13) -0.0108(14) C4 0.0221(15) 0.0257(15) 0.0215(15) -0.0014(13) 0.0064(12) -0.0022(12) C5 0.0256(15) 0.0232(15) 0.0189(14) -0.0011(12) 0.0031(12) -0.0010(12) C6 0.0285(15) 0.0260(16) 0.0204(14) -0.0015(12) 0.0070(12) -0.0053(12) C7 0.0257(15) 0.0255(15) 0.0170(14) -0.0008(12) 0.0083(12) -0.0023(13) C8 0.0251(14) 0.0241(15) 0.0195(14) -0.0010(12) 0.0033(12) -0.0031(12) C9 0.0220(14) 0.0255(16) 0.0183(14) 0.0010(12) 0.0044(11) 0.0036(12) C10 0.048(2) 0.0369(19) 0.0201(16) 0.0001(15) 0.0015(16) 0.0021(17) C11 0.0262(15) 0.0264(16) 0.0183(14) -0.0049(12) 0.0034(12) 0.0021(13) C12 0.0254(15) 0.0299(17) 0.0218(14) -0.0024(13) 0.0023(12) 0.0064(13) C13 0.0210(14) 0.0235(15) 0.0212(14) 0.0015(12) 0.0012(12) 0.0015(11) C14 0.0275(16) 0.0220(14) 0.0206(15) -0.0013(12) 0.0042(13) 0.0008(12) C15 0.0250(15) 0.0245(16) 0.0270(16) -0.0012(13) 0.0037(13) 0.0067(12) C16 0.0262(15) 0.0271(17) 0.0190(15) 0.0015(13) 0.0007(12) 0.0036(13) C17 0.0249(14) 0.0274(16) 0.0189(14) 0.0013(12) 0.0055(12) 0.0003(12) C18 0.0235(15) 0.0289(17) 0.0193(14) -0.0038(12) 0.0089(12) 0.0009(12) OW1 0.0534(19) 0.061(2) 0.058(2) -0.0289(18) -0.0161(16) 0.0280(17) OW2 0.0368(13) 0.0267(12) 0.0284(12) -0.0057(10) 0.0012(10) 0.0011(10) OW3 0.074(3) 0.044(2) 0.104(4) -0.0024(19) -0.003(3) 0.0195(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Gd1 O10 2.365(3) . ? Gd1 O9 2.397(3) . ? Gd1 O1 2.417(2) . ? Gd1 O6 2.431(3) . ? Gd1 O3 2.451(3) . ? Gd1 O11 2.486(3) . ? Gd1 O4 2.486(2) . ? Gd1 O2 2.487(2) . ? Gd1 O5 2.547(3) . ? Gd1 C9 2.820(3) . ? Gd1 C8 2.821(3) . ? Gd1 C17 2.843(3) . ? O1 C8 1.275(4) . ? O2 C8 1.264(4) . ? O3 C9 1.255(4) . ? O4 C9 1.269(4) . ? O5 C17 1.255(4) . ? O6 C17 1.254(4) . ? O7 C18 1.247(4) . ? O8 C18 1.249(4) . ? O8 H8 0.8200 . ? O9 H9A 0.8502 . ? O9 H9B 0.8498 . ? O10 H10A 0.8500 . ? O10 H10C 0.8501 . ? O11 H11B 0.8500 . ? O11 H11C 0.8502 . ? N1 C1 1.322(5) . ? N1 C2 1.381(4) . ? N1 H1A 0.8600 . ? N2 C1 1.343(5) . ? N2 C7 1.386(4) . ? N3 C10 1.337(5) . ? N3 C11 1.398(4) . ? N4 C10 1.322(5) . ? N4 C16 1.376(4) . ? N4 H4A 0.8600 . ? C1 H1B 0.9300 . ? C2 C3 1.386(5) . ? C2 C7 1.409(5) . ? C3 C4 1.386(5) . ? C3 H3B 0.9300 . ? C4 C5 1.417(4) . ? C4 C9 1.507(4) 2_545 ? C5 C6 1.388(4) . ? C5 C8 1.492(4) . ? C6 C7 1.389(5) . ? C6 H6A 0.9300 . ? C9 C4 1.507(4) 2 ? C10 H10B 0.9300 . ? C11 C12 1.385(5) . ? C11 C16 1.392(5) . ? C12 C13 1.381(4) . ? C12 H12A 0.9300 . ? C13 C14 1.420(4) . ? C13 C17 1.503(4) . ? C14 C15 1.380(5) . ? C14 C18 1.522(4) . ? C15 C16 1.392(4) . ? C15 H15A 0.9300 . ? OW1 HW1A 0.8501 . ? OW1 HW1C 0.8499 . ? OW2 HW2B 0.8501 . ? OW2 HW2C 0.8500 . ? OW3 HW3A 0.8497 . ? OW3 HW3B 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 O10 Gd1 O9 76.21(11) . . ? O10 Gd1 O1 137.98(9) . . ? O9 Gd1 O1 90.01(12) . . ? O10 Gd1 O6 88.84(10) . . ? O9 Gd1 O6 76.42(11) . . ? O1 Gd1 O6 126.68(9) . . ? O10 Gd1 O3 127.50(9) . . ? O9 Gd1 O3 148.90(9) . . ? O1 Gd1 O3 82.98(8) . . ? O6 Gd1 O3 83.64(11) . . ? O10 Gd1 O11 79.21(10) . . ? O9 Gd1 O11 136.45(9) . . ? O1 Gd1 O11 84.81(9) . . ? O6 Gd1 O11 138.42(9) . . ? O3 Gd1 O11 73.21(9) . . ? O10 Gd1 O4 75.97(9) . . ? O9 Gd1 O4 134.91(12) . . ? O1 Gd1 O4 133.57(8) . . ? O6 Gd1 O4 68.27(9) . . ? O3 Gd1 O4 53.00(8) . . ? O11 Gd1 O4 70.21(9) . . ? O10 Gd1 O2 84.60(9) . . ? O9 Gd1 O2 72.03(10) . . ? O1 Gd1 O2 53.39(8) . . ? O6 Gd1 O2 148.43(10) . . ? O3 Gd1 O2 124.28(9) . . ? O11 Gd1 O2 70.34(9) . . ? O4 Gd1 O2 138.51(9) . . ? O10 Gd1 O5 132.55(9) . . ? O9 Gd1 O5 69.58(9) . . ? O1 Gd1 O5 74.60(8) . . ? O6 Gd1 O5 52.24(8) . . ? O3 Gd1 O5 79.36(9) . . ? O11 Gd1 O5 147.43(9) . . ? O4 Gd1 O5 106.49(8) . . ? O2 Gd1 O5 113.57(8) . . ? O10 Gd1 C9 102.35(9) . . ? O9 Gd1 C9 149.29(10) . . ? O1 Gd1 C9 108.77(9) . . ? O6 Gd1 C9 72.88(10) . . ? O3 Gd1 C9 26.37(9) . . ? O11 Gd1 C9 71.14(9) . . ? O4 Gd1 C9 26.72(9) . . ? O2 Gd1 C9 138.68(9) . . ? O5 Gd1 C9 91.67(9) . . ? O10 Gd1 C8 111.21(10) . . ? O9 Gd1 C8 79.91(11) . . ? O1 Gd1 C8 26.79(8) . . ? O6 Gd1 C8 144.14(9) . . ? O3 Gd1 C8 104.44(9) . . ? O11 Gd1 C8 76.27(9) . . ? O4 Gd1 C8 143.75(9) . . ? O2 Gd1 C8 26.61(8) . . ? O5 Gd1 C8 94.29(9) . . ? C9 Gd1 C8 127.05(9) . . ? O10 Gd1 C17 111.19(10) . . ? O9 Gd1 C17 70.73(9) . . ? O1 Gd1 C17 100.76(9) . . ? O6 Gd1 C17 26.04(9) . . ? O3 Gd1 C17 80.85(9) . . ? O11 Gd1 C17 152.64(9) . . ? O4 Gd1 C17 87.39(9) . . ? O2 Gd1 C17 134.04(9) . . ? O5 Gd1 C17 26.21(9) . . ? C9 Gd1 C17 81.77(9) . . ? C8 Gd1 C17 119.53(10) . . ? C8 O1 Gd1 94.56(19) . . ? C8 O2 Gd1 91.58(19) . . ? C9 O3 Gd1 93.46(19) . . ? C9 O4 Gd1 91.49(19) . . ? C17 O5 Gd1 90.2(2) . . ? C17 O6 Gd1 95.6(2) . . ? C18 O8 H8 109.5 . . ? Gd1 O9 H9A 109.3 . . ? Gd1 O9 H9B 109.4 . . ? H9A O9 H9B 109.5 . . ? Gd1 O10 H10A 109.4 . . ? Gd1 O10 H10C 109.4 . . ? H10A O10 H10C 109.5 . . ? Gd1 O11 H11B 109.4 . . ? Gd1 O11 H11C 109.3 . . ? H11B O11 H11C 109.5 . . ? C1 N1 C2 104.3(3) . . ? C1 N1 H1A 127.8 . . ? C2 N1 H1A 127.8 . . ? C1 N2 C7 106.4(3) . . ? C10 N3 C11 107.5(3) . . ? C10 N4 C16 108.9(3) . . ? C10 N4 H4A 125.6 . . ? C16 N4 H4A 125.6 . . ? N1 C1 N2 114.3(3) . . ? N1 C1 H1B 122.8 . . ? N2 C1 H1B 122.8 . . ? N1 C2 C3 130.2(3) . . ? N1 C2 C7 109.8(3) . . ? C3 C2 C7 120.0(3) . . ? C4 C3 C2 118.4(3) . . ? C4 C3 H3B 120.8 . . ? C2 C3 H3B 120.8 . . ? C3 C4 C5 121.4(3) . . ? C3 C4 C9 115.4(3) . 2_545 ? C5 C4 C9 123.1(3) . 2_545 ? C6 C5 C4 120.4(3) . . ? C6 C5 C8 118.4(3) . . ? C4 C5 C8 121.2(3) . . ? C5 C6 C7 117.7(3) . . ? C5 C6 H6A 121.2 . . ? C7 C6 H6A 121.2 . . ? N2 C7 C6 132.7(3) . . ? N2 C7 C2 105.2(3) . . ? C6 C7 C2 122.1(3) . . ? O2 C8 O1 120.5(3) . . ? O2 C8 C5 119.9(3) . . ? O1 C8 C5 119.7(3) . . ? O2 C8 Gd1 61.82(17) . . ? O1 C8 Gd1 58.65(16) . . ? C5 C8 Gd1 178.2(2) . . ? O3 C9 O4 121.6(3) . . ? O3 C9 C4 119.4(3) . 2 ? O4 C9 C4 118.8(3) . 2 ? O3 C9 Gd1 60.17(17) . . ? O4 C9 Gd1 61.79(16) . . ? C4 C9 Gd1 169.4(2) 2 . ? N4 C10 N3 110.4(3) . . ? N4 C10 H10B 124.8 . . ? N3 C10 H10B 124.8 . . ? C12 C11 C16 122.4(3) . . ? C12 C11 N3 131.1(3) . . ? C16 C11 N3 106.5(3) . . ? C13 C12 C11 116.8(3) . . ? C13 C12 H12A 121.6 . . ? C11 C12 H12A 121.6 . . ? C12 C13 C14 121.3(3) . . ? C12 C13 C17 117.6(3) . . ? C14 C13 C17 121.0(3) . . ? C15 C14 C13 121.2(3) . . ? C15 C14 C18 119.5(3) . . ? C13 C14 C18 119.3(3) . . ? C14 C15 C16 117.3(3) . . ? C14 C15 H15A 121.3 . . ? C16 C15 H15A 121.3 . . ? N4 C16 C15 132.3(3) . . ? N4 C16 C11 106.7(3) . . ? C15 C16 C11 121.0(3) . . ? O6 C17 O5 122.0(3) . . ? O6 C17 C13 118.1(3) . . ? O5 C17 C13 120.0(3) . . ? O6 C17 Gd1 58.33(18) . . ? O5 C17 Gd1 63.64(18) . . ? C13 C17 Gd1 176.4(2) . . ? O7 C18 O8 127.1(3) . . ? O7 C18 C14 117.0(3) . . ? O8 C18 C14 115.9(3) . . ? HW1A OW1 HW1C 109.5 . . ? HW2B OW2 HW2C 109.5 . . ? HW3A OW3 HW3B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.704 _refine_diff_density_min -0.745 _refine_diff_density_rms 0.115 data_3 _database_code_depnum_ccdc_archive 'CCDC 902076' #================================================================ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H21 N4 O14 Tb' _chemical_formula_weight 676.31 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 11.185(2) _cell_length_b 8.9570(18) _cell_length_c 23.074(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.70(3) _cell_angle_gamma 90.00 _cell_volume 2303.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 20897 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.950 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 3.152 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4475 _exptl_absorpt_correction_T_max 0.4723 _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 Smart APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 20897 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5139 _reflns_number_gt 4679 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5139 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.1314 _refine_ls_wR_factor_gt 0.1223 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.044 _refine_ls_shift/su_mean 0.008 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 0.298099(15) 0.33959(2) 0.235033(8) 0.01632(11) Uani 1 1 d . . . O1 O 0.3931(3) 0.5375(4) 0.29153(13) 0.0273(7) Uani 1 1 d . . . O2 O 0.2953(3) 0.3767(4) 0.34125(14) 0.0270(7) Uani 1 1 d . . . O3 O 0.4779(3) 0.3569(4) 0.18256(16) 0.0272(7) Uani 1 1 d . . . O4 O 0.3705(3) 0.1527(3) 0.16739(16) 0.0253(7) Uani 1 1 d . . . O5 O 0.1946(4) 0.3600(4) 0.13917(16) 0.0339(9) Uani 1 1 d . . . O6 O 0.2547(3) 0.5747(4) 0.17626(13) 0.0267(7) Uani 1 1 d . . . O7 O 0.0116(4) 0.8631(4) 0.15575(18) 0.0391(9) Uani 1 1 d . . . H7 H -0.0145 0.8729 0.1877 0.059 Uiso 1 1 calc R . . O8 O -0.0186(3) 0.6206(4) 0.17267(16) 0.0327(7) Uani 1 1 d . . . O9 O 0.4514(3) 0.1804(4) 0.28698(16) 0.0330(8) Uani 1 1 d . . . H9B H 0.4535 0.0964 0.2700 0.049 Uiso 1 1 d R . . H9C H 0.5195 0.2224 0.2870 0.049 Uiso 1 1 d R . . O10 O 0.1077(3) 0.4364(5) 0.25422(18) 0.0487(11) Uani 1 1 d . . . H10C H 0.1085 0.5310 0.2514 0.073 Uiso 1 1 d R . . H10D H 0.0544 0.4009 0.2297 0.073 Uiso 1 1 d R . . O11 O 0.1835(3) 0.1255(4) 0.24969(18) 0.0320(7) Uani 1 1 d . . . H11A H 0.2184 0.0739 0.2770 0.048 Uiso 1 1 d R . . H11B H 0.1144 0.1512 0.2589 0.048 Uiso 1 1 d R . . N1 N 0.6677(3) 0.1123(5) -0.04910(17) 0.0280(8) Uani 1 1 d . . . H1A H 0.7185 0.0502 -0.0614 0.034 Uiso 1 1 calc R . . N2 N 0.5366(4) 0.2996(5) -0.05024(18) 0.0315(9) Uani 1 1 d . . . N3 N 0.1660(3) 0.5958(5) -0.07708(16) 0.0294(8) Uani 1 1 d . . . H3A H 0.2169 0.5361 -0.0908 0.035 Uiso 1 1 calc R . . N4 N 0.0298(4) 0.7675(5) -0.07348(16) 0.0306(9) Uani 1 1 d . . . C1 C 0.6075(4) 0.2176(6) -0.0805(2) 0.0329(10) Uani 1 1 d . . . H1B H 0.6148 0.2318 -0.1200 0.039 Uiso 1 1 calc R . . C2 C 0.5520(4) 0.2397(5) 0.00522(18) 0.0227(8) Uani 1 1 d . . . C3 C 0.6334(4) 0.1216(5) 0.00620(19) 0.0223(8) Uani 1 1 d . . . C4 C 0.3362(4) 0.5394(5) 0.44329(18) 0.0218(8) Uani 1 1 d . . . H4A H 0.2811 0.4617 0.4429 0.026 Uiso 1 1 calc R . . C5 C 0.3911(4) 0.5781(5) 0.39413(18) 0.0200(8) Uani 1 1 d . . . C6 C 0.5262(4) 0.1972(5) 0.10532(19) 0.0207(8) Uani 1 1 d . . . C7 C 0.4991(4) 0.2806(5) 0.05498(19) 0.0262(9) Uani 1 1 d . . . H7A H 0.4468 0.3614 0.0548 0.031 Uiso 1 1 calc R . . C8 C 0.3578(4) 0.4927(5) 0.33927(18) 0.0206(8) Uani 1 1 d . . . C9 C 0.4553(4) 0.2354(5) 0.15565(18) 0.0223(8) Uani 1 1 d . . . C10 C 0.0962(5) 0.6910(6) -0.1077(2) 0.0349(11) Uani 1 1 d . . . H10A H 0.0941 0.7025 -0.1479 0.042 Uiso 1 1 calc R . . C11 C 0.0568(4) 0.7206(5) -0.01671(18) 0.0225(8) Uani 1 1 d . . . C12 C 0.1437(4) 0.6083(5) -0.01959(18) 0.0218(8) Uani 1 1 d . . . C13 C 0.1884(4) 0.5327(5) 0.02999(19) 0.0237(9) Uani 1 1 d . . . H13A H 0.2442 0.4562 0.0280 0.028 Uiso 1 1 calc R . . C14 C 0.1476(3) 0.5744(5) 0.08194(18) 0.0197(8) Uani 1 1 d . . . C15 C 0.0613(4) 0.6896(5) 0.08491(19) 0.0213(8) Uani 1 1 d . . . C16 C 0.0152(4) 0.7619(5) 0.03564(19) 0.0245(9) Uani 1 1 d . . . H16A H -0.0422 0.8364 0.0375 0.029 Uiso 1 1 calc R . . C17 C 0.2014(4) 0.4994(5) 0.13604(18) 0.0203(8) Uani 1 1 d . . . C18 C 0.0149(4) 0.7268(5) 0.14305(19) 0.0227(9) Uani 1 1 d . . . OW1 O 0.2594(6) -0.1613(5) 0.2634(3) 0.0772(19) Uani 1 1 d . . . HW1A H 0.3042 -0.1873 0.2932 0.116 Uiso 1 1 d R . . HW1B H 0.1868 -0.1816 0.2685 0.116 Uiso 1 1 d R . . OW2 O 0.3265(4) 0.4002(5) -0.1075(2) 0.0541(12) Uani 1 1 d . . . HW2B H 0.3920 0.4178 -0.0873 0.081 Uiso 1 1 d R . . HW2C H 0.3014 0.3137 -0.0994 0.081 Uiso 1 1 d R . . OW3 O -0.1563(3) 0.9532(4) -0.10451(14) 0.0275(7) Uani 1 1 d . . . HW3B H -0.1063 1.0064 -0.1211 0.041 Uiso 1 1 d R . . HW3C H -0.1910 0.8934 -0.1291 0.041 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 Tb1 0.01805(16) 0.01837(16) 0.01306(15) -0.00103(6) 0.00434(10) -0.00104(5) O1 0.0348(17) 0.0314(19) 0.0163(15) -0.0027(12) 0.0048(13) -0.0129(13) O2 0.0394(18) 0.0235(15) 0.0187(15) -0.0029(12) 0.0065(13) -0.0096(13) O3 0.0287(18) 0.0304(18) 0.0234(17) -0.0048(12) 0.0080(15) -0.0057(12) O4 0.0233(17) 0.031(2) 0.0224(18) -0.0043(11) 0.0076(14) -0.0045(11) O5 0.050(2) 0.0221(18) 0.0268(19) 0.0002(13) -0.0154(17) 0.0047(13) O6 0.0331(17) 0.0269(17) 0.0198(15) 0.0012(12) -0.0002(13) -0.0058(12) O7 0.055(2) 0.032(2) 0.034(2) -0.0085(15) 0.0262(19) -0.0042(16) O8 0.0358(18) 0.0347(19) 0.0300(19) 0.0063(15) 0.0175(15) 0.0048(15) O9 0.037(2) 0.037(2) 0.0258(18) 0.0001(14) 0.0052(16) 0.0067(13) O10 0.039(2) 0.065(3) 0.046(2) 0.032(2) 0.0260(18) 0.0255(18) O11 0.0307(17) 0.0259(18) 0.042(2) 0.0009(16) 0.0184(15) -0.0047(13) N1 0.034(2) 0.031(2) 0.0209(19) 0.0001(16) 0.0102(16) 0.0057(17) N2 0.034(2) 0.041(2) 0.0212(19) 0.0109(18) 0.0094(16) 0.0097(17) N3 0.036(2) 0.034(2) 0.0188(18) -0.0050(16) 0.0067(16) 0.0068(16) N4 0.037(2) 0.036(2) 0.0188(18) 0.0036(16) 0.0009(15) 0.0033(16) C1 0.042(3) 0.042(3) 0.016(2) 0.009(2) 0.0088(19) 0.003(2) C2 0.022(2) 0.027(2) 0.019(2) 0.0046(16) 0.0014(16) 0.0037(16) C3 0.021(2) 0.028(2) 0.019(2) 0.0001(17) 0.0071(16) 0.0032(16) C4 0.022(2) 0.025(2) 0.0185(19) 0.0005(16) 0.0024(16) -0.0028(15) C5 0.025(2) 0.019(2) 0.0166(19) -0.0020(15) 0.0042(16) -0.0008(15) C6 0.023(2) 0.022(2) 0.018(2) -0.0001(16) 0.0063(16) 0.0016(16) C7 0.027(2) 0.028(2) 0.024(2) 0.0038(18) 0.0051(17) 0.0090(17) C8 0.022(2) 0.023(2) 0.0167(19) -0.0002(15) 0.0023(16) -0.0011(15) C9 0.023(2) 0.030(2) 0.0143(18) 0.0002(16) 0.0035(15) 0.0078(16) C10 0.045(3) 0.042(3) 0.017(2) 0.000(2) 0.002(2) 0.005(2) C11 0.024(2) 0.025(2) 0.019(2) 0.0005(17) 0.0006(16) 0.0023(16) C12 0.0169(19) 0.030(2) 0.0182(19) -0.0014(17) -0.0015(16) 0.0016(16) C13 0.025(2) 0.027(2) 0.019(2) -0.0018(16) 0.0031(17) 0.0079(16) C14 0.0179(19) 0.021(2) 0.020(2) 0.0019(15) 0.0008(16) 0.0022(15) C15 0.024(2) 0.021(2) 0.020(2) -0.0025(16) 0.0083(17) -0.0017(15) C16 0.025(2) 0.023(2) 0.027(2) -0.0004(17) 0.0039(17) 0.0053(16) C17 0.020(2) 0.027(2) 0.0143(18) 0.0000(15) 0.0030(15) 0.0021(15) C18 0.021(2) 0.027(3) 0.022(2) -0.0003(17) 0.0076(16) 0.0025(16) OW1 0.077(4) 0.041(3) 0.112(6) -0.001(3) -0.006(4) 0.019(2) OW2 0.048(2) 0.056(3) 0.054(3) -0.023(2) -0.019(2) 0.020(2) OW3 0.0308(16) 0.0250(17) 0.0264(16) -0.0046(13) 0.0008(13) -0.0024(12) _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 O11 2.346(3) . ? Tb1 O10 2.375(3) . ? Tb1 O1 2.397(3) . ? Tb1 O5 2.418(3) . ? Tb1 O3 2.436(4) . ? Tb1 O9 2.464(4) . ? Tb1 O4 2.471(3) . ? Tb1 O2 2.476(3) . ? Tb1 O6 2.531(3) . ? Tb1 C9 2.801(4) . ? Tb1 C8 2.802(4) . ? Tb1 C17 2.834(4) . ? O1 C8 1.266(5) . ? O2 C8 1.255(5) . ? O3 C9 1.269(6) . ? O4 C9 1.250(5) . ? O5 C17 1.253(5) . ? O6 C17 1.257(5) . ? O7 C18 1.257(6) . ? O7 H7 0.8200 . ? O8 C18 1.247(6) . ? O9 H9B 0.8501 . ? O9 H9C 0.8499 . ? O10 H10C 0.8499 . ? O10 H10D 0.8499 . ? O11 H11A 0.8499 . ? O11 H11B 0.8500 . ? N1 C1 1.338(6) . ? N1 C3 1.364(6) . ? N1 H1A 0.8600 . ? N2 C1 1.322(6) . ? N2 C2 1.385(6) . ? N3 C10 1.322(7) . ? N3 C12 1.374(5) . ? N3 H3A 0.8600 . ? N4 C10 1.320(7) . ? N4 C11 1.385(6) . ? C1 H1B 0.9300 . ? C2 C7 1.384(6) . ? C2 C3 1.394(6) . ? C3 C4 1.397(6) 2_645 ? C4 C5 1.378(6) . ? C4 C3 1.397(6) 2_655 ? C4 H4A 0.9300 . ? C5 C6 1.410(6) 2_655 ? C5 C8 1.500(6) . ? C6 C7 1.393(6) . ? C6 C5 1.410(6) 2_645 ? C6 C9 1.499(6) . ? C7 H7A 0.9300 . ? C10 H10A 0.9300 . ? C11 C16 1.380(6) . ? C11 C12 1.404(6) . ? C12 C13 1.387(6) . ? C13 C14 1.369(6) . ? C13 H13A 0.9300 . ? C14 C15 1.418(6) . ? C14 C17 1.500(6) . ? C15 C16 1.372(6) . ? C15 C18 1.515(6) . ? C16 H16A 0.9300 . ? OW1 HW1A 0.8499 . ? OW1 HW1B 0.8500 . ? OW2 HW2B 0.8500 . ? OW2 HW2C 0.8500 . ? OW3 HW3B 0.8500 . ? OW3 HW3C 0.8499 . ? 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 O11 Tb1 O10 76.27(14) . . ? O11 Tb1 O1 138.52(12) . . ? O10 Tb1 O1 89.60(15) . . ? O11 Tb1 O5 88.13(14) . . ? O10 Tb1 O5 76.89(14) . . ? O1 Tb1 O5 126.82(11) . . ? O11 Tb1 O3 127.36(11) . . ? O10 Tb1 O3 149.20(12) . . ? O1 Tb1 O3 82.87(11) . . ? O5 Tb1 O3 83.88(14) . . ? O11 Tb1 O9 79.84(13) . . ? O10 Tb1 O9 136.02(12) . . ? O1 Tb1 O9 84.47(12) . . ? O5 Tb1 O9 138.65(12) . . ? O3 Tb1 O9 73.07(12) . . ? O11 Tb1 O4 75.44(12) . . ? O10 Tb1 O4 135.31(15) . . ? O1 Tb1 O4 133.72(11) . . ? O5 Tb1 O4 68.33(12) . . ? O3 Tb1 O4 53.30(11) . . ? O9 Tb1 O4 70.37(12) . . ? O11 Tb1 O2 85.16(12) . . ? O10 Tb1 O2 71.47(13) . . ? O1 Tb1 O2 53.37(10) . . ? O5 Tb1 O2 148.35(13) . . ? O3 Tb1 O2 124.15(12) . . ? O9 Tb1 O2 70.18(12) . . ? O4 Tb1 O2 138.40(12) . . ? O11 Tb1 O6 132.40(12) . . ? O10 Tb1 O6 70.13(11) . . ? O1 Tb1 O6 74.51(11) . . ? O5 Tb1 O6 52.42(10) . . ? O3 Tb1 O6 79.08(11) . . ? O9 Tb1 O6 146.90(11) . . ? O4 Tb1 O6 106.50(11) . . ? O2 Tb1 O6 113.66(11) . . ? O11 Tb1 C9 101.63(13) . . ? O10 Tb1 C9 149.80(13) . . ? O1 Tb1 C9 109.15(12) . . ? O5 Tb1 C9 72.92(13) . . ? O3 Tb1 C9 26.90(12) . . ? O9 Tb1 C9 71.11(12) . . ? O4 Tb1 C9 26.50(12) . . ? O2 Tb1 C9 138.73(11) . . ? O6 Tb1 C9 91.73(12) . . ? O11 Tb1 C8 111.77(13) . . ? O10 Tb1 C8 79.36(15) . . ? O1 Tb1 C8 26.76(11) . . ? O5 Tb1 C8 144.17(12) . . ? O3 Tb1 C8 104.31(12) . . ? O9 Tb1 C8 76.02(12) . . ? O4 Tb1 C8 143.78(12) . . ? O2 Tb1 C8 26.61(11) . . ? O6 Tb1 C8 94.27(11) . . ? C9 Tb1 C8 127.33(12) . . ? O11 Tb1 C17 110.61(14) . . ? O10 Tb1 C17 71.15(12) . . ? O1 Tb1 C17 100.82(12) . . ? O5 Tb1 C17 26.09(11) . . ? O3 Tb1 C17 80.97(12) . . ? O9 Tb1 C17 152.70(12) . . ? O4 Tb1 C17 87.49(12) . . ? O2 Tb1 C17 134.04(12) . . ? O6 Tb1 C17 26.34(11) . . ? C9 Tb1 C17 81.93(12) . . ? C8 Tb1 C17 119.54(13) . . ? C8 O1 Tb1 94.7(2) . . ? C8 O2 Tb1 91.3(3) . . ? C9 O3 Tb1 92.8(3) . . ? C9 O4 Tb1 91.7(3) . . ? C17 O5 Tb1 95.8(3) . . ? C17 O6 Tb1 90.4(3) . . ? C18 O7 H7 109.5 . . ? Tb1 O9 H9B 109.4 . . ? Tb1 O9 H9C 109.4 . . ? H9B O9 H9C 109.5 . . ? Tb1 O10 H10C 109.5 . . ? Tb1 O10 H10D 109.3 . . ? H10C O10 H10D 109.5 . . ? Tb1 O11 H11A 109.2 . . ? Tb1 O11 H11B 109.5 . . ? H11A O11 H11B 109.5 . . ? C1 N1 C3 107.2(4) . . ? C1 N1 H1A 126.4 . . ? C3 N1 H1A 126.4 . . ? C1 N2 C2 103.8(4) . . ? C10 N3 C12 108.5(4) . . ? C10 N3 H3A 125.7 . . ? C12 N3 H3A 125.7 . . ? C10 N4 C11 108.6(4) . . ? N2 C1 N1 113.7(4) . . ? N2 C1 H1B 123.2 . . ? N1 C1 H1B 123.1 . . ? C7 C2 N2 129.4(4) . . ? C7 C2 C3 120.7(4) . . ? N2 C2 C3 109.9(4) . . ? N1 C3 C2 105.3(4) . . ? N1 C3 C4 132.8(4) . 2_645 ? C2 C3 C4 121.8(4) . 2_645 ? C5 C4 C3 117.4(4) . 2_655 ? C5 C4 H4A 121.3 . . ? C3 C4 H4A 121.3 2_655 . ? C4 C5 C6 121.2(4) . 2_655 ? C4 C5 C8 118.0(4) . . ? C6 C5 C8 120.7(4) 2_655 . ? C7 C6 C5 120.7(4) . 2_645 ? C7 C6 C9 115.5(4) . . ? C5 C6 C9 123.6(4) 2_645 . ? C2 C7 C6 118.1(4) . . ? C2 C7 H7A 121.0 . . ? C6 C7 H7A 121.0 . . ? O2 C8 O1 120.6(4) . . ? O2 C8 C5 119.5(4) . . ? O1 C8 C5 119.9(4) . . ? O2 C8 Tb1 62.1(2) . . ? O1 C8 Tb1 58.5(2) . . ? C5 C8 Tb1 178.4(3) . . ? O4 C9 O3 121.8(4) . . ? O4 C9 C6 119.4(4) . . ? O3 C9 C6 118.6(4) . . ? O4 C9 Tb1 61.8(2) . . ? O3 C9 Tb1 60.3(2) . . ? C6 C9 Tb1 169.5(3) . . ? N4 C10 N3 110.6(4) . . ? N4 C10 H10A 124.7 . . ? N3 C10 H10A 124.7 . . ? C16 C11 N4 133.1(4) . . ? C16 C11 C12 121.2(4) . . ? N4 C11 C12 105.7(4) . . ? N3 C12 C13 132.4(4) . . ? N3 C12 C11 106.6(4) . . ? C13 C12 C11 121.0(4) . . ? C14 C13 C12 117.8(4) . . ? C14 C13 H13A 121.1 . . ? C12 C13 H13A 121.1 . . ? C13 C14 C15 121.2(4) . . ? C13 C14 C17 117.8(4) . . ? C15 C14 C17 120.9(4) . . ? C16 C15 C14 121.0(4) . . ? C16 C15 C18 119.8(4) . . ? C14 C15 C18 119.1(4) . . ? C15 C16 C11 117.9(4) . . ? C15 C16 H16A 121.0 . . ? C11 C16 H16A 121.0 . . ? O5 C17 O6 121.3(4) . . ? O5 C17 C14 118.2(4) . . ? O6 C17 C14 120.5(4) . . ? O5 C17 Tb1 58.1(2) . . ? O6 C17 Tb1 63.2(2) . . ? C14 C17 Tb1 176.3(3) . . ? O8 C18 O7 126.7(4) . . ? O8 C18 C15 117.2(4) . . ? O7 C18 C15 116.1(4) . . ? HW1A OW1 HW1B 109.5 . . ? HW2B OW2 HW2C 109.5 . . ? HW3B OW3 HW3C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.927 _refine_diff_density_min -1.729 _refine_diff_density_rms 0.183 data_4 _database_code_depnum_ccdc_archive 'CCDC 902077' #================================================================ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H21 Dy N4 O14' _chemical_formula_weight 679.89 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' Dy Dy -0.1892 4.4098 '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 11.196(8) _cell_length_b 8.962(6) _cell_length_c 23.138(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.772(8) _cell_angle_gamma 90.00 _cell_volume 2313(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 16811 _cell_measurement_theta_min 1.83 _cell_measurement_theta_max 26.96 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.952 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1340 _exptl_absorpt_coefficient_mu 3.312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4468 _exptl_absorpt_correction_T_max 0.4797 _exptl_absorpt_process_details ? _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 'Bruker Smart APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16811 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_av_sigmaI/netI 0.0469 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.96 _reflns_number_total 4609 _reflns_number_gt 3773 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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^)+(0.0416P)^2^+0.8149P] 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 4609 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0747 _refine_ls_wR_factor_gt 0.0695 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Dy1 Dy 0.298306(17) 0.83991(2) 0.235002(8) 0.01901(8) Uani 1 1 d . . . O1 O 0.3935(3) 1.0375(3) 0.29115(12) 0.0280(7) Uani 1 1 d . . . O2 O 0.2954(3) 0.8763(3) 0.34076(13) 0.0277(7) Uani 1 1 d . . . O3 O 0.4765(3) 0.8575(3) 0.18309(14) 0.0303(7) Uani 1 1 d . . . O4 O 0.3697(3) 0.6533(3) 0.16797(13) 0.0272(7) Uani 1 1 d . . . O5 O 0.1948(3) 0.8598(3) 0.13972(14) 0.0373(8) Uani 1 1 d . . . O6 O 0.2548(3) 1.0748(3) 0.17622(13) 0.0291(7) Uani 1 1 d . . . O7 O 0.0101(3) 1.3635(4) 0.15579(15) 0.0431(9) Uani 1 1 d . . . O8 O -0.0178(3) 1.1211(4) 0.17272(14) 0.0358(8) Uani 1 1 d . . . H8 H -0.0413 1.1528 0.2031 0.054 Uiso 1 1 calc R . . O9 O 0.1836(3) 0.6279(3) 0.25050(14) 0.0327(8) Uani 1 1 d . . . H9A H 0.2142 0.5819 0.2803 0.049 Uiso 1 1 d R . . H9C H 0.1830 0.5711 0.2211 0.049 Uiso 1 1 d R . . O10 O 0.1072(3) 0.9354(4) 0.25333(15) 0.0502(10) Uani 1 1 d . . . H10A H 0.0914 0.9102 0.2873 0.075 Uiso 1 1 d R . . H10C H 0.1082 1.0300 0.2508 0.075 Uiso 1 1 d R . . O11 O 0.4516(3) 0.6812(3) 0.28650(14) 0.0350(8) Uani 1 1 d . . . H11A H 0.4324 0.6650 0.3207 0.052 Uiso 1 1 d R . . H11B H 0.4557 0.5987 0.2686 0.052 Uiso 1 1 d R . . N1 N 0.3325(3) 1.1127(4) 0.54898(15) 0.0293(9) Uani 1 1 d . . . H1A H 0.2819 1.0508 0.5615 0.035 Uiso 1 1 calc R . . N2 N 0.4637(4) 1.2996(4) 0.54999(16) 0.0313(9) Uani 1 1 d . . . N3 N 0.1658(3) 1.0958(4) -0.07726(15) 0.0304(9) Uani 1 1 d . . . H3A H 0.2169 1.0365 -0.0909 0.037 Uiso 1 1 calc R . . N4 N 0.0286(4) 1.2682(4) -0.07347(15) 0.0310(9) Uani 1 1 d . . . C1 C 0.3930(4) 1.2186(5) 0.58012(19) 0.0303(10) Uani 1 1 d . . . H1B H 0.3857 1.2334 0.6194 0.036 Uiso 1 1 calc R . . C2 C 0.4478(4) 1.2405(5) 0.49437(18) 0.0263(10) Uani 1 1 d . . . C3 C 0.5007(4) 1.2800(5) 0.44445(19) 0.0283(10) Uani 1 1 d . . . H3B H 0.5532 1.3605 0.4446 0.034 Uiso 1 1 calc R . . C4 C 0.4743(4) 1.1982(4) 0.39456(18) 0.0227(9) Uani 1 1 d . . . C5 C 0.3919(4) 1.0776(5) 0.39394(18) 0.0241(9) Uani 1 1 d . . . C6 C 0.3361(4) 1.0405(5) 0.44330(18) 0.0249(9) Uani 1 1 d . . . H6A H 0.2802 0.9636 0.4427 0.030 Uiso 1 1 calc R . . C7 C 0.3661(4) 1.1212(5) 0.49350(18) 0.0235(9) Uani 1 1 d . . . C8 C 0.3594(4) 0.9919(5) 0.33883(17) 0.0230(9) Uani 1 1 d . . . C9 C 0.4544(4) 0.7357(5) 0.15582(18) 0.0244(9) Uani 1 1 d . . . C10 C 0.0958(5) 1.1906(5) -0.1075(2) 0.0367(12) Uani 1 1 d . . . H10B H 0.0936 1.2018 -0.1475 0.044 Uiso 1 1 calc R . . C11 C 0.1426(4) 1.1083(5) -0.01961(19) 0.0248(9) Uani 1 1 d . . . C12 C 0.1886(4) 1.0318(5) 0.02978(18) 0.0265(10) Uani 1 1 d . . . H12A H 0.2445 0.9557 0.0276 0.032 Uiso 1 1 calc R . . C13 C 0.1475(4) 1.0740(5) 0.08229(18) 0.0238(9) Uani 1 1 d . . . C14 C 0.0615(4) 1.1894(4) 0.08523(18) 0.0227(9) Uani 1 1 d . . . C15 C 0.0157(4) 1.2623(5) 0.03590(19) 0.0265(10) Uani 1 1 d . . . H15A H -0.0408 1.3378 0.0378 0.032 Uiso 1 1 calc R . . C16 C 0.0565(4) 1.2195(5) -0.01705(19) 0.0250(9) Uani 1 1 d . . . C17 C 0.2017(4) 1.0000(5) 0.13654(18) 0.0238(9) Uani 1 1 d . . . C18 C 0.0153(4) 1.2281(5) 0.14317(19) 0.0279(10) Uani 1 1 d . . . OW1 O 0.3250(3) 0.6031(4) 0.39239(17) 0.0574(11) Uani 1 1 d . . . HW1A H 0.3397 0.6638 0.4203 0.086 Uiso 1 1 d R . . HW1C H 0.3814 0.5396 0.3922 0.086 Uiso 1 1 d R . . OW2 O 0.1562(3) 0.5473(3) 0.10428(13) 0.0303(7) Uani 1 1 d . . . HW2B H 0.2259 0.5522 0.1218 0.045 Uiso 1 1 d R . . HW2C H 0.1046 0.5384 0.1290 0.045 Uiso 1 1 d R . . OW3 O 0.2588(5) 0.3416(4) 0.2642(2) 0.0804(15) Uani 1 1 d . . . HW3A H 0.2443 0.2983 0.2317 0.121 Uiso 1 1 d R . . HW3B H 0.3235 0.3073 0.2810 0.121 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 Dy1 0.02051(12) 0.02123(11) 0.01585(12) -0.00102(8) 0.00488(8) -0.00104(8) O1 0.0344(18) 0.0313(16) 0.0191(16) -0.0030(13) 0.0076(13) -0.0084(14) O2 0.0384(19) 0.0237(15) 0.0220(16) -0.0016(12) 0.0073(14) -0.0101(13) O3 0.0335(19) 0.0300(16) 0.0291(18) -0.0079(14) 0.0128(14) -0.0047(13) O4 0.0236(17) 0.0334(17) 0.0255(17) -0.0014(13) 0.0068(13) -0.0023(13) O5 0.051(2) 0.0271(17) 0.0311(19) 0.0005(14) -0.0097(16) 0.0033(15) O6 0.0348(19) 0.0302(16) 0.0214(16) 0.0012(13) -0.0027(14) -0.0040(14) O7 0.059(2) 0.0364(19) 0.038(2) -0.0060(15) 0.0280(18) -0.0015(17) O8 0.040(2) 0.0391(18) 0.0309(19) 0.0033(15) 0.0191(16) 0.0061(15) O9 0.0352(19) 0.0289(16) 0.0358(19) -0.0001(14) 0.0127(15) -0.0044(14) O10 0.049(2) 0.060(2) 0.045(2) 0.0266(19) 0.0264(18) 0.0203(19) O11 0.042(2) 0.0405(19) 0.0226(17) 0.0000(14) 0.0035(15) 0.0077(15) N1 0.034(2) 0.034(2) 0.021(2) -0.0017(16) 0.0116(17) -0.0072(17) N2 0.034(2) 0.038(2) 0.022(2) -0.0073(17) 0.0067(17) -0.0062(18) N3 0.037(2) 0.036(2) 0.019(2) -0.0019(16) 0.0051(17) 0.0102(18) N4 0.039(2) 0.036(2) 0.0172(19) 0.0017(16) 0.0004(17) 0.0061(18) C1 0.033(3) 0.041(3) 0.017(2) -0.004(2) 0.001(2) 0.002(2) C2 0.027(2) 0.030(2) 0.022(2) -0.0075(18) 0.0063(19) -0.0027(19) C3 0.025(2) 0.033(2) 0.028(3) -0.006(2) 0.008(2) -0.011(2) C4 0.025(2) 0.020(2) 0.024(2) 0.0000(17) 0.0067(19) 0.0026(17) C5 0.027(2) 0.026(2) 0.020(2) -0.0014(17) 0.0056(18) 0.0008(18) C6 0.025(2) 0.026(2) 0.025(2) 0.0003(18) 0.0097(19) -0.0056(18) C7 0.023(2) 0.027(2) 0.021(2) 0.0019(17) 0.0063(18) 0.0008(18) C8 0.024(2) 0.025(2) 0.020(2) -0.0015(17) 0.0015(18) -0.0012(18) C9 0.023(2) 0.034(2) 0.016(2) 0.0058(18) 0.0013(18) 0.0075(19) C10 0.048(3) 0.042(3) 0.020(2) 0.001(2) 0.003(2) -0.002(2) C11 0.024(2) 0.025(2) 0.025(2) -0.0052(18) 0.0055(19) -0.0015(18) C12 0.030(2) 0.029(2) 0.021(2) -0.0015(18) 0.0029(19) 0.0063(19) C13 0.023(2) 0.027(2) 0.022(2) -0.0006(17) 0.0025(18) -0.0007(18) C14 0.020(2) 0.026(2) 0.023(2) -0.0031(17) 0.0046(18) 0.0014(17) C15 0.023(2) 0.027(2) 0.030(3) 0.0036(19) 0.0068(19) 0.0037(18) C16 0.023(2) 0.028(2) 0.023(2) 0.0026(18) 0.0000(18) -0.0030(19) C17 0.024(2) 0.028(2) 0.020(2) 0.0001(18) 0.0099(18) 0.0034(19) C18 0.025(2) 0.031(2) 0.028(3) 0.002(2) 0.008(2) -0.001(2) OW1 0.056(3) 0.055(2) 0.058(3) 0.018(2) -0.014(2) -0.020(2) OW2 0.0283(17) 0.0335(17) 0.0293(17) -0.0042(14) 0.0035(14) 0.0007(14) OW3 0.085(3) 0.048(3) 0.104(4) -0.011(2) -0.013(3) 0.025(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 Dy1 O9 2.338(3) . ? Dy1 O10 2.375(4) . ? Dy1 O1 2.394(3) . ? Dy1 O5 2.411(3) . ? Dy1 O3 2.417(3) . ? Dy1 O4 2.459(3) . ? Dy1 O11 2.459(3) . ? Dy1 O2 2.472(3) . ? Dy1 O6 2.532(3) . ? Dy1 C9 2.795(4) . ? Dy1 C8 2.797(4) . ? Dy1 C17 2.830(4) . ? O1 C8 1.265(5) . ? O2 C8 1.263(5) . ? O3 C9 1.275(5) . ? O4 C9 1.251(5) . ? O5 C17 1.261(5) . ? O6 C17 1.247(5) . ? O7 C18 1.251(5) . ? O8 C18 1.251(5) . ? O8 H8 0.8200 . ? O9 H9A 0.8500 . ? O9 H9C 0.8500 . ? O10 H10A 0.8499 . ? O10 H10C 0.8499 . ? O11 H11A 0.8499 . ? O11 H11B 0.8500 . ? N1 C1 1.341(6) . ? N1 C7 1.370(5) . ? N1 H1A 0.8600 . ? N2 C1 1.316(6) . ? N2 C2 1.389(5) . ? N3 C10 1.316(6) . ? N3 C11 1.384(6) . ? N3 H3A 0.8600 . ? N4 C10 1.329(6) . ? N4 C16 1.387(5) . ? C1 H1B 0.9300 . ? C2 C3 1.388(6) . ? C2 C7 1.406(6) . ? C3 C4 1.379(6) . ? C3 H3B 0.9300 . ? C4 C5 1.420(6) . ? C4 C9 1.505(6) 2_655 ? C5 C6 1.387(6) . ? C5 C8 1.507(6) . ? C6 C7 1.386(6) . ? C6 H6A 0.9300 . ? C9 C4 1.505(6) 2_645 ? C10 H10B 0.9300 . ? C11 C16 1.391(6) . ? C11 C12 1.394(6) . ? C12 C13 1.387(6) . ? C12 H12A 0.9300 . ? C13 C14 1.418(6) . ? C13 C17 1.502(6) . ? C14 C15 1.376(6) . ? C14 C18 1.516(6) . ? C15 C16 1.396(6) . ? C15 H15A 0.9300 . ? OW1 HW1A 0.8500 . ? OW1 HW1C 0.8501 . ? OW2 HW2B 0.8501 . ? OW2 HW2C 0.8499 . ? OW3 HW3A 0.8501 . ? OW3 HW3B 0.8499 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 Dy1 O10 75.56(12) . . ? O9 Dy1 O1 138.04(11) . . ? O10 Dy1 O1 90.23(13) . . ? O9 Dy1 O5 88.39(11) . . ? O10 Dy1 O5 76.39(12) . . ? O1 Dy1 O5 126.88(10) . . ? O9 Dy1 O3 128.02(10) . . ? O10 Dy1 O3 149.09(11) . . ? O1 Dy1 O3 82.68(10) . . ? O5 Dy1 O3 83.95(13) . . ? O9 Dy1 O4 75.86(11) . . ? O10 Dy1 O4 134.63(12) . . ? O1 Dy1 O4 133.77(11) . . ? O5 Dy1 O4 68.31(11) . . ? O3 Dy1 O4 53.57(10) . . ? O9 Dy1 O11 79.96(12) . . ? O10 Dy1 O11 136.42(11) . . ? O1 Dy1 O11 84.46(11) . . ? O5 Dy1 O11 138.51(11) . . ? O3 Dy1 O11 72.98(12) . . ? O4 Dy1 O11 70.24(11) . . ? O9 Dy1 O2 84.41(10) . . ? O10 Dy1 O2 71.90(11) . . ? O1 Dy1 O2 53.64(9) . . ? O5 Dy1 O2 148.28(12) . . ? O3 Dy1 O2 124.25(10) . . ? O4 Dy1 O2 138.24(10) . . ? O11 Dy1 O2 70.29(11) . . ? O9 Dy1 O6 132.43(11) . . ? O10 Dy1 O6 70.16(11) . . ? O1 Dy1 O6 74.54(11) . . ? O5 Dy1 O6 52.46(10) . . ? O3 Dy1 O6 78.96(10) . . ? O4 Dy1 O6 106.55(11) . . ? O11 Dy1 O6 146.78(11) . . ? O2 Dy1 O6 113.85(10) . . ? O9 Dy1 C9 102.14(12) . . ? O10 Dy1 C9 149.19(12) . . ? O1 Dy1 C9 109.17(12) . . ? O5 Dy1 C9 72.82(13) . . ? O3 Dy1 C9 27.10(11) . . ? O4 Dy1 C9 26.58(11) . . ? O11 Dy1 C9 71.06(12) . . ? O2 Dy1 C9 138.90(11) . . ? O6 Dy1 C9 91.64(12) . . ? O9 Dy1 C8 111.24(12) . . ? O10 Dy1 C8 80.27(13) . . ? O1 Dy1 C8 26.80(10) . . ? O5 Dy1 C8 144.51(11) . . ? O3 Dy1 C8 104.00(12) . . ? O4 Dy1 C8 143.49(11) . . ? O11 Dy1 C8 75.78(12) . . ? O2 Dy1 C8 26.84(11) . . ? O6 Dy1 C8 94.52(12) . . ? C9 Dy1 C8 127.17(13) . . ? O9 Dy1 C17 110.95(12) . . ? O10 Dy1 C17 70.83(12) . . ? O1 Dy1 C17 100.66(12) . . ? O5 Dy1 C17 26.33(11) . . ? O3 Dy1 C17 80.95(12) . . ? O4 Dy1 C17 87.68(12) . . ? O11 Dy1 C17 152.61(11) . . ? O2 Dy1 C17 133.99(11) . . ? O6 Dy1 C17 26.14(10) . . ? C9 Dy1 C17 81.93(12) . . ? C8 Dy1 C17 119.63(13) . . ? C8 O1 Dy1 94.7(2) . . ? C8 O2 Dy1 91.1(2) . . ? C9 O3 Dy1 93.2(3) . . ? C9 O4 Dy1 91.9(3) . . ? C17 O5 Dy1 95.7(3) . . ? C17 O6 Dy1 90.4(2) . . ? C18 O8 H8 109.5 . . ? Dy1 O9 H9A 109.2 . . ? Dy1 O9 H9C 109.3 . . ? H9A O9 H9C 109.5 . . ? Dy1 O10 H10A 109.2 . . ? Dy1 O10 H10C 109.3 . . ? H10A O10 H10C 109.5 . . ? Dy1 O11 H11A 109.3 . . ? Dy1 O11 H11B 109.3 . . ? H11A O11 H11B 109.5 . . ? C1 N1 C7 107.4(4) . . ? C1 N1 H1A 126.3 . . ? C7 N1 H1A 126.3 . . ? C1 N2 C2 104.1(4) . . ? C10 N3 C11 107.9(4) . . ? C10 N3 H3A 126.0 . . ? C11 N3 H3A 126.0 . . ? C10 N4 C16 107.4(4) . . ? N2 C1 N1 113.9(4) . . ? N2 C1 H1B 123.1 . . ? N1 C1 H1B 123.1 . . ? C3 C2 N2 130.0(4) . . ? C3 C2 C7 120.3(4) . . ? N2 C2 C7 109.6(4) . . ? C4 C3 C2 118.9(4) . . ? C4 C3 H3B 120.5 . . ? C2 C3 H3B 120.5 . . ? C3 C4 C5 120.5(4) . . ? C3 C4 C9 116.0(4) . 2_655 ? C5 C4 C9 123.2(4) . 2_655 ? C6 C5 C4 120.7(4) . . ? C6 C5 C8 118.7(4) . . ? C4 C5 C8 120.5(4) . . ? C7 C6 C5 118.1(4) . . ? C7 C6 H6A 121.0 . . ? C5 C6 H6A 121.0 . . ? N1 C7 C6 133.7(4) . . ? N1 C7 C2 104.9(4) . . ? C6 C7 C2 121.4(4) . . ? O2 C8 O1 120.6(4) . . ? O2 C8 C5 119.1(4) . . ? O1 C8 C5 120.3(4) . . ? O2 C8 Dy1 62.1(2) . . ? O1 C8 Dy1 58.5(2) . . ? C5 C8 Dy1 178.5(3) . . ? O4 C9 O3 120.9(4) . . ? O4 C9 C4 120.2(4) . 2_645 ? O3 C9 C4 118.8(4) . 2_645 ? O4 C9 Dy1 61.5(2) . . ? O3 C9 Dy1 59.7(2) . . ? C4 C9 Dy1 169.5(3) 2_645 . ? N3 C10 N4 111.4(4) . . ? N3 C10 H10B 124.3 . . ? N4 C10 H10B 124.3 . . ? N3 C11 C16 106.6(4) . . ? N3 C11 C12 131.6(4) . . ? C16 C11 C12 121.8(4) . . ? C13 C12 C11 117.2(4) . . ? C13 C12 H12A 121.4 . . ? C11 C12 H12A 121.4 . . ? C12 C13 C14 121.1(4) . . ? C12 C13 C17 118.1(4) . . ? C14 C13 C17 120.7(4) . . ? C15 C14 C13 120.9(4) . . ? C15 C14 C18 119.6(4) . . ? C13 C14 C18 119.4(4) . . ? C14 C15 C16 118.1(4) . . ? C14 C15 H15A 121.0 . . ? C16 C15 H15A 121.0 . . ? N4 C16 C11 106.7(4) . . ? N4 C16 C15 132.5(4) . . ? C11 C16 C15 120.8(4) . . ? O6 C17 O5 121.4(4) . . ? O6 C17 C13 120.9(4) . . ? O5 C17 C13 117.7(4) . . ? O6 C17 Dy1 63.5(2) . . ? O5 C17 Dy1 57.9(2) . . ? C13 C17 Dy1 175.7(3) . . ? O7 C18 O8 126.4(4) . . ? O7 C18 C14 117.0(4) . . ? O8 C18 C14 116.5(4) . . ? HW1A OW1 HW1C 109.5 . . ? HW2B OW2 HW2C 109.5 . . ? HW3A OW3 HW3B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.914 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.747 _refine_diff_density_min -0.720 _refine_diff_density_rms 0.127 data_5 _database_code_depnum_ccdc_archive 'CCDC 902078' #================================================================ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 N2 O9 Tb' _chemical_formula_weight 461.13 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 6.5059(6) _cell_length_b 9.8342(8) _cell_length_c 10.9444(9) _cell_angle_alpha 99.882(7) _cell_angle_beta 106.505(7) _cell_angle_gamma 106.190(7) _cell_volume 620.36(9) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3681 _cell_measurement_theta_min 3.36 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 442 _exptl_absorpt_coefficient_mu 5.756 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5216 _exptl_absorpt_correction_T_max 0.5701 _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 Smart APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3681 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2173 _reflns_number_gt 2071 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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^)+(0.0394P)^2^+0.7948P] 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 2173 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0698 _refine_ls_wR_factor_gt 0.0689 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Tb1 Tb 0.32318(4) 0.39717(2) 0.68970(2) 0.01289(11) Uani 1 1 d . . . O1 O 0.1588(6) 0.3054(4) 0.4548(3) 0.0184(8) Uani 1 1 d . . . O2 O -0.1609(7) 0.1160(5) 0.4098(4) 0.0367(11) Uani 1 1 d . . . O3 O -0.0210(6) 0.5123(4) 0.3297(4) 0.0224(8) Uani 1 1 d . . . O4 O 0.2913(7) 0.5384(4) 0.2807(4) 0.0256(9) Uani 1 1 d . . . O5 O 0.3956(7) 0.3249(4) 0.8921(3) 0.0252(9) Uani 1 1 d . . . O6 O 0.4771(7) 0.6031(4) 0.8862(3) 0.0196(8) Uani 1 1 d . . . O7 O 0.0117(7) 0.1894(4) 0.6659(4) 0.0263(9) Uani 1 1 d . . . H7B H -0.0461 0.1271 0.5771 0.040 Uiso 1 1 d R . . H7C H -0.1066 0.2208 0.6836 0.040 Uiso 1 1 d R . . O8 O 0.4216(6) 0.1786(4) 0.6339(4) 0.0227(8) Uani 1 1 d . . . H8A H 0.3676 0.1105 0.6806 0.034 Uiso 1 1 d R . . H8C H 0.3509 0.1331 0.5402 0.034 Uiso 1 1 d R . . O9 O 0.4187(7) 0.6099(4) 0.5994(4) 0.0246(9) Uani 1 1 d . . . H9B H 0.3483 0.5784 0.5046 0.037 Uiso 1 1 d R . . H9C H 0.5816 0.6510 0.6233 0.037 Uiso 1 1 d R . . N1 N -0.2381(8) 0.1030(5) -0.1768(4) 0.0189(10) Uani 1 1 d . . . N2 N -0.3334(7) -0.0918(5) -0.0978(4) 0.0160(9) Uani 1 1 d . . . H2A H -0.3869 -0.1821 -0.0977 0.019 Uiso 1 1 calc R . . C1 C -0.3336(9) -0.0402(6) -0.2051(5) 0.0178(11) Uani 1 1 d . . . H1B H -0.3961 -0.1012 -0.2912 0.021 Uiso 1 1 calc R . . C2 C -0.1683(9) 0.1513(6) -0.0395(5) 0.0153(11) Uani 1 1 d . . . C3 C -0.0558(9) 0.2917(6) 0.0463(5) 0.0169(11) Uani 1 1 d . . . H3A H -0.0106 0.3724 0.0141 0.020 Uiso 1 1 calc R . . C4 C -0.0120(8) 0.3097(5) 0.1798(5) 0.0122(10) Uani 1 1 d . . . C5 C -0.0761(9) 0.1862(6) 0.2287(5) 0.0143(10) Uani 1 1 d . . . C6 C -0.1856(8) 0.0448(5) 0.1450(5) 0.0136(10) Uani 1 1 d . . . H6B H -0.2274 -0.0362 0.1773 0.016 Uiso 1 1 calc R . . C7 C -0.2301(8) 0.0297(6) 0.0110(5) 0.0138(10) Uani 1 1 d . . . C8 C 0.0941(8) 0.4634(5) 0.2711(5) 0.0137(10) Uani 1 1 d . . . C9 C -0.0218(9) 0.2031(6) 0.3753(5) 0.0167(11) Uani 1 1 d . . . C10 C 0.4763(9) 0.4183(6) 1.0015(5) 0.0163(11) 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 0.01410(16) 0.01256(16) 0.01096(16) 0.00237(10) 0.00447(11) 0.00350(11) O1 0.017(2) 0.022(2) 0.0126(18) 0.0038(16) 0.0033(15) 0.0039(17) O2 0.037(3) 0.036(3) 0.0138(19) 0.0043(18) 0.0057(18) -0.018(2) O3 0.019(2) 0.023(2) 0.026(2) 0.0016(16) 0.0100(17) 0.0096(17) O4 0.020(2) 0.017(2) 0.034(2) 0.0001(17) 0.0113(18) 0.0008(17) O5 0.043(3) 0.016(2) 0.0094(18) 0.0014(15) 0.0038(17) 0.0070(18) O6 0.029(2) 0.018(2) 0.0110(18) 0.0052(15) 0.0054(16) 0.0069(17) O7 0.018(2) 0.027(2) 0.024(2) 0.0040(17) 0.0070(17) -0.0042(17) O8 0.026(2) 0.014(2) 0.027(2) 0.0061(16) 0.0072(17) 0.0078(17) O9 0.028(2) 0.024(2) 0.020(2) 0.0051(17) 0.0089(17) 0.0067(18) N1 0.021(2) 0.019(3) 0.012(2) 0.0022(18) 0.0043(18) 0.003(2) N2 0.019(2) 0.011(2) 0.017(2) 0.0019(18) 0.0056(18) 0.0043(19) C1 0.019(3) 0.019(3) 0.013(3) 0.001(2) 0.005(2) 0.006(2) C2 0.019(3) 0.017(3) 0.013(2) 0.004(2) 0.005(2) 0.010(2) C3 0.021(3) 0.011(3) 0.021(3) 0.006(2) 0.010(2) 0.004(2) C4 0.007(2) 0.011(3) 0.016(2) 0.002(2) 0.0031(19) 0.001(2) C5 0.016(3) 0.018(3) 0.009(2) 0.004(2) 0.006(2) 0.005(2) C6 0.012(3) 0.011(3) 0.017(3) 0.007(2) 0.004(2) 0.002(2) C7 0.013(3) 0.017(3) 0.014(2) 0.005(2) 0.005(2) 0.008(2) C8 0.013(3) 0.013(3) 0.015(3) 0.005(2) 0.003(2) 0.005(2) C9 0.020(3) 0.017(3) 0.015(3) 0.005(2) 0.007(2) 0.009(2) C10 0.016(3) 0.013(3) 0.020(3) 0.008(2) 0.007(2) 0.004(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 Tb1 O4 2.320(4) 2_666 ? Tb1 O3 2.346(4) 2_566 ? Tb1 O7 2.357(4) . ? Tb1 O1 2.381(3) . ? Tb1 O5 2.402(4) . ? Tb1 O6 2.425(4) . ? Tb1 O8 2.438(4) . ? Tb1 O9 2.465(4) . ? O1 C9 1.269(7) . ? O2 C9 1.252(6) . ? O3 C8 1.254(6) . ? O3 Tb1 2.346(4) 2_566 ? O4 C8 1.253(6) . ? O4 Tb1 2.320(4) 2_666 ? O5 C10 1.245(6) . ? O6 C10 1.249(6) 2_667 ? O7 H7B 0.9600 . ? O7 H7C 0.9600 . ? O8 H8A 0.9600 . ? O8 H8C 0.9600 . ? O9 H9B 0.9600 . ? O9 H9C 0.9600 . ? N1 C1 1.311(7) . ? N1 C2 1.392(6) . ? N2 C1 1.355(7) . ? N2 C7 1.381(6) . ? N2 H2A 0.8600 . ? C1 H1B 0.9300 . ? C2 C3 1.387(7) . ? C2 C7 1.408(7) . ? C3 C4 1.375(7) . ? C3 H3A 0.9300 . ? C4 C5 1.415(7) . ? C4 C8 1.506(7) . ? C5 C6 1.386(7) . ? C5 C9 1.511(7) . ? C6 C7 1.384(7) . ? C6 H6B 0.9300 . ? C10 O6 1.249(6) 2_667 ? C10 C10 1.557(10) 2_667 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Tb1 O3 144.05(13) 2_666 2_566 ? O4 Tb1 O7 139.55(14) 2_666 . ? O3 Tb1 O7 76.39(14) 2_566 . ? O4 Tb1 O1 100.50(13) 2_666 . ? O3 Tb1 O1 85.13(13) 2_566 . ? O7 Tb1 O1 79.11(13) . . ? O4 Tb1 O5 89.59(14) 2_666 . ? O3 Tb1 O5 106.85(13) 2_566 . ? O7 Tb1 O5 71.00(14) . . ? O1 Tb1 O5 143.60(13) . . ? O4 Tb1 O6 80.51(13) 2_666 . ? O3 Tb1 O6 77.35(13) 2_566 . ? O7 Tb1 O6 119.97(13) . . ? O1 Tb1 O6 149.22(13) . . ? O5 Tb1 O6 66.70(12) . . ? O4 Tb1 O8 69.30(13) 2_666 . ? O3 Tb1 O8 144.67(13) 2_566 . ? O7 Tb1 O8 71.86(13) . . ? O1 Tb1 O8 74.14(13) . . ? O5 Tb1 O8 77.11(12) . . ? O6 Tb1 O8 132.58(13) . . ? O4 Tb1 O9 73.43(13) 2_666 . ? O3 Tb1 O9 74.40(13) 2_566 . ? O7 Tb1 O9 141.03(14) . . ? O1 Tb1 O9 73.26(13) . . ? O5 Tb1 O9 142.72(13) . . ? O6 Tb1 O9 77.71(12) . . ? O8 Tb1 O9 123.93(12) . . ? C9 O1 Tb1 134.2(3) . . ? C8 O3 Tb1 146.3(3) . 2_566 ? C8 O4 Tb1 160.0(3) . 2_666 ? C10 O5 Tb1 120.9(3) . . ? C10 O6 Tb1 120.2(3) 2_667 . ? Tb1 O7 H7B 109.4 . . ? Tb1 O7 H7C 109.4 . . ? H7B O7 H7C 109.5 . . ? Tb1 O8 H8A 109.3 . . ? Tb1 O8 H8C 109.4 . . ? H8A O8 H8C 109.5 . . ? Tb1 O9 H9B 109.4 . . ? Tb1 O9 H9C 109.3 . . ? H9B O9 H9C 109.5 . . ? C1 N1 C2 104.6(4) . . ? C1 N2 C7 106.4(4) . . ? C1 N2 H2A 126.8 . . ? C7 N2 H2A 126.8 . . ? N1 C1 N2 114.1(4) . . ? N1 C1 H1B 122.9 . . ? N2 C1 H1B 122.9 . . ? C3 C2 N1 130.8(5) . . ? C3 C2 C7 119.9(4) . . ? N1 C2 C7 109.3(4) . . ? C4 C3 C2 119.0(5) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 120.3(5) . . ? C3 C4 C8 118.6(4) . . ? C5 C4 C8 121.0(4) . . ? C6 C5 C4 121.7(4) . . ? C6 C5 C9 117.2(4) . . ? C4 C5 C9 121.1(4) . . ? C5 C6 C7 117.0(4) . . ? C5 C6 H6B 121.5 . . ? C7 C6 H6B 121.5 . . ? N2 C7 C6 132.3(5) . . ? N2 C7 C2 105.5(4) . . ? C6 C7 C2 122.2(5) . . ? O3 C8 O4 123.1(5) . . ? O3 C8 C4 118.9(4) . . ? O4 C8 C4 118.0(4) . . ? O2 C9 O1 124.6(5) . . ? O2 C9 C5 117.4(5) . . ? O1 C9 C5 118.0(4) . . ? O5 C10 O6 127.8(5) . 2_667 ? O5 C10 C10 116.3(6) . 2_667 ? O6 C10 C10 115.9(6) 2_667 2_667 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.717 _refine_diff_density_min -0.912 _refine_diff_density_rms 0.157 data_6 _database_code_depnum_ccdc_archive 'CCDC 902079' #================================================================ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H10 Ho N2 O9' _chemical_formula_weight 467.13 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' Ho Ho -0.2175 4.6783 '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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.482(2) _cell_length_b 9.848(3) _cell_length_c 10.907(4) _cell_angle_alpha 100.004(3) _cell_angle_beta 106.484(3) _cell_angle_gamma 106.293(3) _cell_volume 616.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4388 _cell_measurement_theta_min 2.03 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 446 _exptl_absorpt_coefficient_mu 6.478 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5103 _exptl_absorpt_correction_T_max 0.5636 _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 'Bruker Smart APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4388 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2137 _reflns_number_gt 2061 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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^)+(0.0356P)^2^+1.4957P] 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 2137 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0221 _refine_ls_R_factor_gt 0.0212 _refine_ls_wR_factor_ref 0.0614 _refine_ls_wR_factor_gt 0.0609 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _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 Ho1 Ho 0.32330(3) 0.39741(2) 0.190253(19) 0.01364(10) Uani 1 1 d . . . O1 O 0.7057(6) 0.4607(4) 0.2172(4) 0.0274(8) Uani 1 1 d . . . O2 O 1.0214(6) 0.4863(4) 0.1697(4) 0.0235(8) Uani 1 1 d . . . O3 O 0.8391(6) 0.6912(4) 0.0434(3) 0.0198(7) Uani 1 1 d . . . O4 O 1.1562(7) 0.8850(4) 0.0892(4) 0.0371(10) Uani 1 1 d . . . O5 O 0.4740(6) 0.6026(4) 0.3855(3) 0.0211(7) Uani 1 1 d . . . O6 O 0.3985(7) 0.3248(4) 0.3916(3) 0.0252(8) Uani 1 1 d . . . O7 O 0.4177(6) 0.6081(4) 0.1003(4) 0.0253(8) Uani 1 1 d . . . H7A H 0.3701 0.6729 0.1327 0.038 Uiso 1 1 d R . . H7B H 0.5624 0.6442 0.1209 0.038 Uiso 1 1 d R . . O8 O 0.0137(6) 0.1924(4) 0.1665(4) 0.0276(8) Uani 1 1 d . . . H8A H 0.0583 0.1447 0.2202 0.041 Uiso 1 1 d R . . H8B H -0.0899 0.2205 0.1840 0.041 Uiso 1 1 d R . . O9 O 0.4194(6) 0.1809(4) 0.1329(4) 0.0245(8) Uani 1 1 d . . . H9A H 0.3718 0.1204 0.1743 0.037 Uiso 1 1 d R . . H9B H 0.3555 0.1410 0.0496 0.037 Uiso 1 1 d R . . N1 N 1.2406(8) 0.8984(5) 0.6780(4) 0.0209(9) Uani 1 1 d . . . H1A H 1.2247 0.8459 0.7323 0.025 Uiso 1 1 calc R . . N2 N 1.3356(7) 1.0933(4) 0.5999(4) 0.0167(8) Uani 1 1 d . . . C1 C 1.3367(8) 1.0415(5) 0.7074(5) 0.0195(10) Uiso 1 1 d . . . H1B H 1.4000 1.1021 0.7941 0.023 Uiso 1 1 calc R . . C2 C 1.1697(8) 0.8494(5) 0.5404(5) 0.0147(9) Uani 1 1 d . . . C3 C 1.0580(9) 0.7079(5) 0.4548(5) 0.0191(10) Uani 1 1 d . . . H3A H 1.0160 0.6273 0.4876 0.023 Uiso 1 1 calc R . . C4 C 1.0105(8) 0.6896(5) 0.3199(5) 0.0156(9) Uani 1 1 d . . . C5 C 1.0721(8) 0.8129(5) 0.2704(5) 0.0151(9) Uani 1 1 d . . . C6 C 1.1838(8) 0.9548(5) 0.3553(5) 0.0168(10) Uani 1 1 d . . . H6B H 1.2262 1.0359 0.3231 0.020 Uiso 1 1 calc R . . C7 C 1.2291(8) 0.9698(5) 0.4897(5) 0.0155(9) Uani 1 1 d . . . C8 C 0.9039(8) 0.5351(5) 0.2281(5) 0.0158(10) Uani 1 1 d . . . C9 C 1.0191(8) 0.7961(5) 0.1239(5) 0.0169(10) Uani 1 1 d . . . C10 C 0.5213(8) 0.5807(5) 0.4983(5) 0.0173(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ho1 0.01441(14) 0.01342(14) 0.01076(14) 0.00182(9) 0.00440(9) 0.00235(9) O1 0.0214(19) 0.0216(19) 0.036(2) 0.0030(16) 0.0124(17) 0.0028(16) O2 0.0190(18) 0.0238(18) 0.0264(19) -0.0005(15) 0.0116(15) 0.0065(15) O3 0.0199(18) 0.0200(17) 0.0128(17) 0.0016(14) 0.0036(14) 0.0012(14) O4 0.041(2) 0.031(2) 0.0167(19) 0.0035(16) 0.0084(18) -0.0170(18) O5 0.030(2) 0.0188(17) 0.0122(17) 0.0045(14) 0.0056(15) 0.0072(15) O6 0.039(2) 0.0162(17) 0.0124(17) 0.0026(14) 0.0027(16) 0.0043(16) O7 0.029(2) 0.0246(19) 0.024(2) 0.0083(15) 0.0120(16) 0.0093(16) O8 0.0230(19) 0.030(2) 0.024(2) 0.0091(16) 0.0066(16) 0.0009(16) O9 0.0240(19) 0.0163(17) 0.028(2) 0.0053(15) 0.0057(16) 0.0034(15) N1 0.028(2) 0.022(2) 0.012(2) 0.0047(17) 0.0075(17) 0.0068(18) N2 0.017(2) 0.019(2) 0.0114(19) -0.0002(16) 0.0036(16) 0.0056(17) C2 0.015(2) 0.017(2) 0.015(2) 0.0059(18) 0.0049(19) 0.0075(19) C3 0.024(3) 0.016(2) 0.018(3) 0.0055(19) 0.008(2) 0.006(2) C4 0.011(2) 0.018(2) 0.017(2) 0.0032(19) 0.0045(19) 0.0053(19) C5 0.015(2) 0.019(2) 0.012(2) 0.0048(18) 0.0046(19) 0.0071(19) C6 0.014(2) 0.014(2) 0.020(3) 0.0050(19) 0.005(2) 0.0013(19) C7 0.012(2) 0.014(2) 0.019(2) 0.0018(18) 0.0065(19) 0.0021(18) C8 0.018(2) 0.014(2) 0.017(2) 0.0071(19) 0.006(2) 0.007(2) C9 0.016(2) 0.018(2) 0.014(2) 0.0034(19) 0.003(2) 0.004(2) C10 0.019(2) 0.018(2) 0.012(2) 0.0021(19) 0.0034(19) 0.0053(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 Ho1 O1 2.297(4) . ? Ho1 O8 2.328(4) . ? Ho1 O2 2.329(3) 1_455 ? Ho1 O3 2.356(3) 2_665 ? Ho1 O6 2.389(3) . ? Ho1 O5 2.406(3) . ? Ho1 O9 2.414(3) . ? Ho1 O7 2.445(4) . ? O1 C8 1.248(6) . ? O2 C8 1.261(6) . ? O2 Ho1 2.329(3) 1_655 ? O3 C9 1.275(6) . ? O3 Ho1 2.356(3) 2_665 ? O4 C9 1.253(6) . ? O5 C10 1.253(6) . ? O6 C10 1.251(6) 2_666 ? O7 H7A 0.8500 . ? O7 H7B 0.8500 . ? O8 H8A 0.8500 . ? O8 H8B 0.8499 . ? O9 H9A 0.8500 . ? O9 H9B 0.8499 . ? N1 C1 1.309(7) . ? N1 C2 1.389(6) . ? N1 H1A 0.8600 . ? N2 C1 1.357(6) . ? N2 C7 1.397(6) . ? C1 H1B 0.9300 . ? C2 C3 1.392(7) . ? C2 C7 1.397(7) . ? C3 C4 1.382(7) . ? C3 H3A 0.9300 . ? C4 C5 1.416(7) . ? C4 C8 1.510(6) . ? C5 C6 1.392(7) . ? C5 C9 1.504(7) . ? C6 C7 1.384(7) . ? C6 H6B 0.9300 . ? C10 O6 1.251(6) 2_666 ? C10 C10 1.544(9) 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 O1 Ho1 O8 139.62(13) . . ? O1 Ho1 O2 144.18(13) . 1_455 ? O8 Ho1 O2 76.20(13) . 1_455 ? O1 Ho1 O3 99.70(13) . 2_665 ? O8 Ho1 O3 79.66(12) . 2_665 ? O2 Ho1 O3 84.59(12) 1_455 2_665 ? O1 Ho1 O6 89.64(14) . . ? O8 Ho1 O6 71.16(13) . . ? O2 Ho1 O6 107.73(13) 1_455 . ? O3 Ho1 O6 143.97(12) 2_665 . ? O1 Ho1 O5 81.48(13) . . ? O8 Ho1 O5 119.72(13) . . ? O2 Ho1 O5 77.13(12) 1_455 . ? O3 Ho1 O5 148.28(12) 2_665 . ? O6 Ho1 O5 67.30(11) . . ? O1 Ho1 O9 69.19(12) . . ? O8 Ho1 O9 71.94(13) . . ? O2 Ho1 O9 144.25(12) 1_455 . ? O3 Ho1 O9 74.23(12) 2_665 . ? O6 Ho1 O9 76.91(12) . . ? O5 Ho1 O9 133.45(12) . . ? O1 Ho1 O7 73.34(13) . . ? O8 Ho1 O7 140.82(13) . . ? O2 Ho1 O7 74.21(13) 1_455 . ? O3 Ho1 O7 72.55(12) 2_665 . ? O6 Ho1 O7 142.95(12) . . ? O5 Ho1 O7 77.60(12) . . ? O9 Ho1 O7 123.77(12) . . ? C8 O1 Ho1 160.5(3) . . ? C8 O2 Ho1 146.4(3) . 1_655 ? C9 O3 Ho1 133.8(3) . 2_665 ? C10 O5 Ho1 119.7(3) . . ? C10 O6 Ho1 120.2(3) 2_666 . ? Ho1 O7 H7A 109.5 . . ? Ho1 O7 H7B 109.3 . . ? H7A O7 H7B 109.5 . . ? Ho1 O8 H8A 109.3 . . ? Ho1 O8 H8B 109.3 . . ? H8A O8 H8B 109.5 . . ? Ho1 O9 H9A 109.4 . . ? Ho1 O9 H9B 109.3 . . ? H9A O9 H9B 109.5 . . ? C1 N1 C2 105.3(4) . . ? C1 N1 H1A 127.4 . . ? C2 N1 H1A 127.4 . . ? C1 N2 C7 105.8(4) . . ? N1 C1 N2 113.9(4) . . ? N1 C1 H1B 123.1 . . ? N2 C1 H1B 123.1 . . ? N1 C2 C3 130.6(4) . . ? N1 C2 C7 109.3(4) . . ? C3 C2 C7 120.1(4) . . ? C4 C3 C2 118.7(4) . . ? C4 C3 H3A 120.7 . . ? C2 C3 H3A 120.7 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 C8 118.5(4) . . ? C5 C4 C8 121.0(4) . . ? C6 C5 C4 121.4(4) . . ? C6 C5 C9 117.2(4) . . ? C4 C5 C9 121.4(4) . . ? C5 C6 C7 116.9(4) . . ? C5 C6 H6B 121.5 . . ? C7 C6 H6B 121.5 . . ? N2 C7 C6 131.7(4) . . ? N2 C7 C2 105.7(4) . . ? C6 C7 C2 122.5(4) . . ? O1 C8 O2 123.3(4) . . ? O1 C8 C4 118.0(4) . . ? O2 C8 C4 118.7(4) . . ? O4 C9 O3 124.4(5) . . ? O4 C9 C5 117.8(4) . . ? O3 C9 C5 117.8(4) . . ? O5 C10 O6 127.2(4) . 2_666 ? O5 C10 C10 116.3(5) . 2_666 ? O6 C10 C10 116.5(5) 2_666 2_666 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.928 _refine_diff_density_min -0.940 _refine_diff_density_rms 0.138 data_7 _database_code_depnum_ccdc_archive 'CCDC 902080' #================================================================ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 N2 O8 Yb' _chemical_formula_weight 457.22 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' Yb Yb -0.3850 5.5486 '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' _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 6.733(2) _cell_length_b 7.450(3) _cell_length_c 12.049(4) _cell_angle_alpha 87.684(4) _cell_angle_beta 77.440(4) _cell_angle_gamma 80.434(3) _cell_volume 581.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4004 _cell_measurement_theta_min 1.73 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 8.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3767 _exptl_absorpt_correction_T_max 0.4436 _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 'Bruker Smart APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4004 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2005 _reflns_number_gt 1927 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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^)+(0.0246P)^2^+1.4340P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0009(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2005 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0207 _refine_ls_R_factor_gt 0.0194 _refine_ls_wR_factor_ref 0.0489 _refine_ls_wR_factor_gt 0.0483 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 Yb1 Yb -0.17872(3) 0.16438(2) -0.076786(15) 0.01275(10) Uani 1 1 d . . . O1 O -0.3097(5) 0.0060(4) -0.1918(3) 0.0200(7) Uani 1 1 d . . . O2 O -0.1482(5) -0.2807(4) -0.1994(3) 0.0219(7) Uani 1 1 d . . . O3 O -0.8890(5) 0.0345(4) -0.2030(3) 0.0196(7) Uani 1 1 d . . . O4 O -0.6748(5) -0.1469(4) -0.1128(3) 0.0193(7) Uani 1 1 d . . . O5 O -0.7642(5) 0.5403(4) 0.0025(3) 0.0196(7) Uani 1 1 d . . . O6 O -0.5249(5) 0.3000(4) -0.0638(3) 0.0175(7) Uani 1 1 d . . . O7 O -0.1049(4) -0.1562(4) -0.0122(3) 0.0160(7) Uani 1 1 d . . . H7A H -0.2233 -0.1894 0.0412 0.019 Uiso 1 1 calc R . . H7B H -0.0693 -0.2389 -0.0762 0.019 Uiso 1 1 calc R . . O8 O -0.1242(5) 0.3595(4) -0.2338(3) 0.0223(7) Uani 1 1 d . . . H8A H 0.0053 0.3150 -0.2835 0.034 Uiso 1 1 d R . . H8B H -0.1217 0.4793 -0.2082 0.034 Uiso 1 1 d R . . N1 N -0.5893(7) -0.2794(6) -0.6070(3) 0.0265(10) Uani 1 1 d . . . H1A H -0.7065 -0.2639 -0.6266 0.032 Uiso 1 1 calc R . . N2 N -0.2508(7) -0.3583(6) -0.6214(3) 0.0268(10) Uani 1 1 d . . . C1 C -0.4048(9) -0.3486(8) -0.6721(4) 0.0299(12) Uani 1 1 d . . . H1B H -0.3888 -0.3861 -0.7467 0.036 Uiso 1 1 calc R . . C2 C -0.3406(7) -0.2889(6) -0.5132(4) 0.0181(10) Uani 1 1 d . . . C3 C -0.2501(7) -0.2679(7) -0.4223(4) 0.0189(10) Uani 1 1 d . . . H3A H -0.1093 -0.3041 -0.4278 0.023 Uiso 1 1 calc R . . C4 C -0.3748(7) -0.1917(6) -0.3238(4) 0.0150(9) Uani 1 1 d . . . C5 C -0.5902(7) -0.1403(6) -0.3135(4) 0.0150(9) Uani 1 1 d . . . C6 C -0.6815(7) -0.1623(7) -0.4041(4) 0.0196(10) Uani 1 1 d . . . H6A H -0.8225 -0.1275 -0.3986 0.024 Uiso 1 1 calc R . . C7 C -0.5542(7) -0.2382(6) -0.5030(4) 0.0196(10) Uani 1 1 d . . . C8 C -0.2722(6) -0.1536(6) -0.2298(4) 0.0156(9) Uani 1 1 d . . . C9 C -0.7288(6) -0.0771(6) -0.2014(4) 0.0142(9) Uani 1 1 d . . . C10 C -0.5849(7) 0.4554(6) -0.0167(4) 0.0161(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Yb1 0.01428(13) 0.01242(13) 0.01161(13) -0.00147(7) -0.00344(8) -0.00112(7) O1 0.0240(17) 0.0163(18) 0.0221(18) -0.0068(14) -0.0102(14) -0.0011(13) O2 0.0308(18) 0.0145(17) 0.0222(18) -0.0045(14) -0.0136(15) 0.0024(14) O3 0.0180(16) 0.0218(18) 0.0165(17) -0.0003(14) -0.0019(13) 0.0016(13) O4 0.0199(16) 0.0239(18) 0.0120(16) -0.0003(13) -0.0021(13) 0.0012(13) O5 0.0209(17) 0.0137(17) 0.0247(18) -0.0037(14) -0.0055(14) -0.0022(13) O6 0.0197(16) 0.0149(17) 0.0183(17) -0.0044(13) -0.0056(13) -0.0008(12) O7 0.0171(15) 0.0170(17) 0.0150(16) -0.0043(13) -0.0032(12) -0.0053(12) O8 0.0256(17) 0.0157(18) 0.0226(18) 0.0023(14) -0.0003(14) -0.0014(13) N1 0.031(2) 0.037(3) 0.017(2) -0.0019(19) -0.0132(18) -0.0082(19) N2 0.034(2) 0.032(3) 0.014(2) -0.0045(18) -0.0003(18) -0.0091(19) C1 0.046(3) 0.034(3) 0.011(2) -0.006(2) -0.003(2) -0.013(2) C2 0.025(2) 0.016(2) 0.013(2) -0.0007(18) -0.0020(19) -0.0062(19) C3 0.018(2) 0.022(3) 0.016(2) -0.0036(19) -0.0008(18) -0.0030(18) C4 0.019(2) 0.014(2) 0.013(2) 0.0019(18) -0.0058(18) -0.0035(17) C5 0.019(2) 0.013(2) 0.013(2) -0.0020(18) -0.0019(18) -0.0027(17) C6 0.018(2) 0.027(3) 0.015(2) 0.001(2) -0.0054(18) -0.0034(19) C7 0.030(3) 0.016(2) 0.015(2) 0.0000(19) -0.006(2) -0.0069(19) C8 0.017(2) 0.020(3) 0.010(2) 0.0017(18) -0.0027(17) -0.0044(18) C9 0.017(2) 0.013(2) 0.013(2) -0.0035(17) -0.0007(17) -0.0033(17) C10 0.021(2) 0.016(2) 0.012(2) 0.0023(18) -0.0052(18) -0.0038(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 Yb1 O1 2.258(3) . ? Yb1 O4 2.290(3) 2_455 ? Yb1 O3 2.292(3) 1_655 ? Yb1 O8 2.341(3) . ? Yb1 O5 2.349(3) 2_465 ? Yb1 O6 2.356(3) . ? Yb1 O7 2.376(3) 2 ? Yb1 O7 2.486(3) . ? Yb1 C10 3.131(5) 2_465 ? Yb1 C10 3.162(5) . ? Yb1 Yb1 3.8504(8) 2 ? O1 C8 1.257(6) . ? O2 C8 1.253(5) . ? O3 C9 1.251(5) . ? O3 Yb1 2.292(3) 1_455 ? O4 C9 1.267(5) . ? O4 Yb1 2.290(3) 2_455 ? O5 C10 1.244(5) . ? O5 Yb1 2.349(3) 2_465 ? O6 C10 1.274(6) . ? O7 Yb1 2.376(3) 2 ? O7 H7A 0.9700 . ? O7 H7B 0.9700 . ? O8 H8A 0.9600 . ? O8 H8B 0.9600 . ? N1 C1 1.350(7) . ? N1 C7 1.380(6) . ? N1 H1A 0.8600 . ? N2 C1 1.305(7) . ? N2 C2 1.393(6) . ? C1 H1B 0.9300 . ? C2 C3 1.390(7) . ? C2 C7 1.404(7) . ? C3 C4 1.378(6) . ? C3 H3A 0.9300 . ? C4 C5 1.416(6) . ? C4 C8 1.507(6) . ? C5 C6 1.392(6) . ? C5 C9 1.508(6) . ? C6 C7 1.386(7) . ? C6 H6A 0.9300 . ? C10 C10 1.544(9) 2_465 ? C10 Yb1 3.131(5) 2_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 O1 Yb1 O4 114.83(12) . 2_455 ? O1 Yb1 O3 77.52(12) . 1_655 ? O4 Yb1 O3 138.64(11) 2_455 1_655 ? O1 Yb1 O8 83.92(12) . . ? O4 Yb1 O8 144.90(12) 2_455 . ? O3 Yb1 O8 72.00(11) 1_655 . ? O1 Yb1 O5 138.39(11) . 2_465 ? O4 Yb1 O5 72.70(12) 2_455 2_465 ? O3 Yb1 O5 125.51(11) 1_655 2_465 ? O8 Yb1 O5 73.96(12) . 2_465 ? O1 Yb1 O6 72.91(11) . . ? O4 Yb1 O6 75.93(11) 2_455 . ? O3 Yb1 O6 142.62(11) 1_655 . ? O8 Yb1 O6 82.51(11) . . ? O5 Yb1 O6 69.64(11) 2_465 . ? O1 Yb1 O7 143.11(11) . 2 ? O4 Yb1 O7 76.73(11) 2_455 2 ? O3 Yb1 O7 72.79(11) 1_655 2 ? O8 Yb1 O7 106.63(11) . 2 ? O5 Yb1 O7 77.91(11) 2_465 2 ? O6 Yb1 O7 142.41(11) . 2 ? O1 Yb1 O7 76.07(11) . . ? O4 Yb1 O7 71.22(11) 2_455 . ? O3 Yb1 O7 74.46(11) 1_655 . ? O8 Yb1 O7 143.88(11) . . ? O5 Yb1 O7 138.90(11) 2_465 . ? O6 Yb1 O7 118.59(10) . . ? O7 Yb1 O7 75.28(11) 2 . ? O1 Yb1 C10 120.15(11) . 2_465 ? O4 Yb1 C10 69.03(11) 2_455 2_465 ? O3 Yb1 C10 141.25(11) 1_655 2_465 ? O8 Yb1 C10 75.90(12) . 2_465 ? O5 Yb1 C10 20.55(11) 2_465 2_465 ? O6 Yb1 C10 49.17(11) . 2_465 ? O7 Yb1 C10 96.74(11) 2 2_465 ? O7 Yb1 C10 140.22(11) . 2_465 ? O1 Yb1 C10 93.23(11) . . ? O4 Yb1 C10 70.17(11) 2_455 . ? O3 Yb1 C10 151.03(11) 1_655 . ? O8 Yb1 C10 79.82(11) . . ? O5 Yb1 C10 48.93(11) 2_465 . ? O6 Yb1 C10 20.82(11) . . ? O7 Yb1 C10 123.14(11) 2 . ? O7 Yb1 C10 130.40(11) . . ? C10 Yb1 C10 28.41(15) 2_465 . ? O1 Yb1 Yb1 109.77(8) . 2 ? O4 Yb1 Yb1 69.54(8) 2_455 2 ? O3 Yb1 Yb1 69.17(8) 1_655 2 ? O8 Yb1 Yb1 134.27(8) . 2 ? O5 Yb1 Yb1 110.93(8) 2_465 2 ? O6 Yb1 Yb1 142.93(8) . 2 ? O7 Yb1 Yb1 38.64(8) 2 2 ? O7 Yb1 Yb1 36.65(7) . 2 ? C10 Yb1 Yb1 124.65(8) 2_465 2 ? C10 Yb1 Yb1 139.10(8) . 2 ? C8 O1 Yb1 135.9(3) . . ? C9 O3 Yb1 138.2(3) . 1_455 ? C9 O4 Yb1 137.0(3) . 2_455 ? C10 O5 Yb1 118.0(3) . 2_465 ? C10 O6 Yb1 118.1(3) . . ? Yb1 O7 Yb1 104.72(11) 2 . ? Yb1 O7 H7A 110.8 2 . ? Yb1 O7 H7A 110.8 . . ? Yb1 O7 H7B 110.8 2 . ? Yb1 O7 H7B 110.8 . . ? H7A O7 H7B 108.9 . . ? Yb1 O8 H8A 109.4 . . ? Yb1 O8 H8B 109.4 . . ? H8A O8 H8B 109.5 . . ? C1 N1 C7 106.9(4) . . ? C1 N1 H1A 126.5 . . ? C7 N1 H1A 126.5 . . ? C1 N2 C2 104.4(4) . . ? N2 C1 N1 114.1(4) . . ? N2 C1 H1B 122.9 . . ? N1 C1 H1B 122.9 . . ? C3 C2 N2 129.7(4) . . ? C3 C2 C7 120.5(4) . . ? N2 C2 C7 109.8(4) . . ? C4 C3 C2 118.1(4) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C3 C4 C5 121.4(4) . . ? C3 C4 C8 117.6(4) . . ? C5 C4 C8 120.9(4) . . ? C6 C5 C4 120.6(4) . . ? C6 C5 C9 118.1(4) . . ? C4 C5 C9 121.0(4) . . ? C7 C6 C5 117.4(4) . . ? C7 C6 H6A 121.3 . . ? C5 C6 H6A 121.3 . . ? N1 C7 C6 133.3(5) . . ? N1 C7 C2 104.7(4) . . ? C6 C7 C2 121.9(4) . . ? O2 C8 O1 124.9(4) . . ? O2 C8 C4 117.6(4) . . ? O1 C8 C4 117.4(4) . . ? O3 C9 O4 125.4(4) . . ? O3 C9 C5 118.2(4) . . ? O4 C9 C5 116.4(4) . . ? O5 C10 O6 126.0(4) . . ? O5 C10 C10 118.3(5) . 2_465 ? O6 C10 C10 115.6(5) . 2_465 ? O5 C10 Yb1 41.5(2) . 2_465 ? O6 C10 Yb1 167.0(3) . 2_465 ? C10 C10 Yb1 76.9(3) 2_465 2_465 ? O5 C10 Yb1 166.8(3) . . ? O6 C10 Yb1 41.1(2) . . ? C10 C10 Yb1 74.7(3) 2_465 . ? Yb1 C10 Yb1 151.59(15) 2_465 . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.036 _refine_diff_density_min -1.193 _refine_diff_density_rms 0.130 data_8 _database_code_depnum_ccdc_archive 'CCDC 902081' #================================================================ _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H8 N2 O8 Pr' _chemical_formula_weight 425.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.501(7) _cell_length_b 9.435(9) _cell_length_c 9.706(9) _cell_angle_alpha 117.238(10) _cell_angle_beta 93.257(11) _cell_angle_gamma 99.498(11) _cell_volume 595.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4165 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 25.00 _exptl_crystal_description green _exptl_crystal_colour block _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 410 _exptl_absorpt_coefficient_mu 4.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5951 _exptl_absorpt_correction_T_max 0.6366 _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 'Bruker Smart APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 4165 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2052 _reflns_number_gt 1832 _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, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXP-97 _computing_publication_material 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^)+(0.0513P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2052 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0359 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0782 _refine_ls_wR_factor_gt 0.0740 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pr1 Pr 0.12095(4) 0.83999(4) 0.31803(3) 0.01495(13) Uani 1 1 d . . . O1 O 0.3800(5) 1.0821(5) 0.4303(5) 0.0200(9) Uani 1 1 d . . . O2 O 0.6531(5) 1.2346(5) 0.5586(4) 0.0196(9) Uani 1 1 d . . . O3 O 0.8621(5) 1.0093(5) 0.3880(4) 0.0192(9) Uani 1 1 d . . . O4 O 1.0377(5) 1.0354(5) 0.2252(5) 0.0222(9) Uani 1 1 d . . . O5 O -0.0773(5) 0.6792(5) 0.0565(4) 0.0193(9) Uani 1 1 d . . . O6 O -0.1089(6) 0.4647(5) -0.1789(4) 0.0218(9) Uani 1 1 d . . . O7 O -0.1624(6) 0.6983(5) 0.3773(5) 0.0338(11) Uani 1 1 d . . . H7A H -0.1492 0.7256 0.4744 0.051 Uiso 1 1 d R . . H7B H -0.2558 0.7276 0.3539 0.051 Uiso 1 1 d R . . N1 N 0.6733(6) 1.2233(6) -0.0992(5) 0.0196(11) Uani 1 1 d . . . N2 N 0.4172(6) 1.2719(6) -0.0004(6) 0.0225(11) Uani 1 1 d . . . H2A H 0.3127 1.2987 0.0099 0.027 Uiso 1 1 calc R . . C1 C 0.5192(8) 1.2670(7) -0.1111(7) 0.0227(13) Uani 1 1 d . . . H1B H 0.4834 1.2924 -0.1890 0.027 Uiso 1 1 calc R . . C2 C 0.6721(8) 1.1984(7) 0.0318(6) 0.0164(12) Uani 1 1 d . . . C3 C 0.7975(7) 1.1467(7) 0.0994(6) 0.0143(11) Uani 1 1 d . . . H3A H 0.9051 1.1254 0.0587 0.017 Uiso 1 1 calc R . . C4 C 0.7590(7) 1.1272(7) 0.2296(6) 0.0161(12) Uani 1 1 d . . . C5 C 0.5922(7) 1.1551(6) 0.2876(6) 0.0152(12) Uani 1 1 d . . . C6 C 0.4671(8) 1.2034(7) 0.2183(7) 0.0200(12) Uani 1 1 d . . . H6A H 0.3566 1.2198 0.2552 0.024 Uiso 1 1 calc R . . C7 C 0.5093(8) 1.2268(7) 0.0925(7) 0.0174(12) Uani 1 1 d . . . C8 C 0.8946(7) 1.0566(7) 0.2855(6) 0.0158(12) Uani 1 1 d . . . C9 C 0.5402(7) 1.1520(7) 0.4340(6) 0.0151(12) Uani 1 1 d . . . C10 C -0.0545(7) 0.5407(7) -0.0360(7) 0.0172(12) Uani 1 1 d . . . OW1 O -0.1765(8) 0.5438(7) 0.5592(7) 0.0604(16) Uani 1 1 d . . . HW1A H -0.0965 0.5261 0.6115 0.091 Uiso 1 1 d R . . HW1B H -0.2442 0.5995 0.6203 0.091 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 0.01256(18) 0.02114(19) 0.01288(19) 0.00870(14) 0.00309(12) 0.00574(12) O1 0.013(2) 0.033(2) 0.020(2) 0.0172(19) 0.0030(17) 0.0047(17) O2 0.019(2) 0.026(2) 0.014(2) 0.0098(18) 0.0013(17) 0.0067(17) O3 0.024(2) 0.026(2) 0.016(2) 0.0145(18) 0.0103(17) 0.0118(17) O4 0.018(2) 0.037(2) 0.021(2) 0.019(2) 0.0094(18) 0.0122(18) O5 0.015(2) 0.020(2) 0.017(2) 0.0032(18) 0.0009(17) 0.0085(16) O6 0.030(2) 0.023(2) 0.010(2) 0.0047(18) -0.0005(18) 0.0085(18) O7 0.034(3) 0.036(3) 0.034(3) 0.018(2) 0.012(2) 0.008(2) N1 0.020(3) 0.027(3) 0.018(3) 0.014(2) 0.008(2) 0.010(2) N2 0.013(3) 0.039(3) 0.028(3) 0.023(3) 0.006(2) 0.012(2) C1 0.019(3) 0.034(3) 0.025(3) 0.021(3) 0.000(3) 0.009(3) C2 0.021(3) 0.019(3) 0.008(3) 0.004(2) 0.005(2) 0.008(2) C3 0.008(3) 0.026(3) 0.015(3) 0.013(3) 0.007(2) 0.008(2) C4 0.014(3) 0.022(3) 0.013(3) 0.008(2) 0.002(2) 0.007(2) C5 0.015(3) 0.019(3) 0.015(3) 0.010(2) 0.005(2) 0.005(2) C6 0.010(3) 0.030(3) 0.024(3) 0.015(3) 0.008(2) 0.008(2) C7 0.016(3) 0.025(3) 0.015(3) 0.012(3) -0.001(2) 0.005(2) C8 0.014(3) 0.018(3) 0.016(3) 0.009(2) 0.004(2) 0.003(2) C9 0.016(3) 0.020(3) 0.017(3) 0.012(3) 0.007(2) 0.011(2) C10 0.009(3) 0.024(3) 0.022(3) 0.013(3) 0.006(2) 0.004(2) OW1 0.076(4) 0.053(4) 0.063(4) 0.038(3) 0.010(3) 0.008(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 O2 2.395(4) 2_676 ? Pr1 O1 2.489(4) . ? Pr1 O5 2.501(4) . ? Pr1 O3 2.522(4) 2_676 ? Pr1 O4 2.537(4) 1_455 ? Pr1 O6 2.539(5) 2_565 ? Pr1 O7 2.557(5) . ? Pr1 N1 2.601(5) 2_675 ? Pr1 O3 2.639(4) 1_455 ? Pr1 C8 2.972(6) 1_455 ? O1 C9 1.262(7) . ? O2 C9 1.261(7) . ? O2 Pr1 2.395(4) 2_676 ? O3 C8 1.284(6) . ? O3 Pr1 2.522(4) 2_676 ? O3 Pr1 2.639(4) 1_655 ? O4 C8 1.252(7) . ? O4 Pr1 2.537(4) 1_655 ? O5 C10 1.249(7) . ? O6 C10 1.238(7) . ? O6 Pr1 2.539(5) 2_565 ? O7 H7A 0.8500 . ? O7 H7B 0.8500 . ? N1 C1 1.306(7) . ? N1 C2 1.395(7) . ? N1 Pr1 2.601(5) 2_675 ? N2 C1 1.342(8) . ? N2 C7 1.360(7) . ? N2 H2A 0.8600 . ? C1 H1B 0.9300 . ? C2 C3 1.388(8) . ? C2 C7 1.398(8) . ? C3 C4 1.397(8) . ? C3 H3A 0.9300 . ? C4 C5 1.416(8) . ? C4 C8 1.505(8) . ? C5 C6 1.375(8) . ? C5 C9 1.506(7) . ? C6 C7 1.381(8) . ? C6 H6A 0.9300 . ? C8 Pr1 2.972(6) 1_655 ? C10 C10 1.544(11) 2_565 ? OW1 HW1A 0.8500 . ? OW1 HW1B 0.8500 . ? 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 Pr1 O1 76.04(14) 2_676 . ? O2 Pr1 O5 130.37(13) 2_676 . ? O1 Pr1 O5 133.55(13) . . ? O2 Pr1 O3 69.62(13) 2_676 2_676 ? O1 Pr1 O3 70.61(13) . 2_676 ? O5 Pr1 O3 147.40(13) . 2_676 ? O2 Pr1 O4 148.74(14) 2_676 1_455 ? O1 Pr1 O4 73.24(14) . 1_455 ? O5 Pr1 O4 71.02(14) . 1_455 ? O3 Pr1 O4 104.78(14) 2_676 1_455 ? O2 Pr1 O6 67.53(13) 2_676 2_565 ? O1 Pr1 O6 132.36(14) . 2_565 ? O5 Pr1 O6 63.92(12) . 2_565 ? O3 Pr1 O6 120.13(12) 2_676 2_565 ? O4 Pr1 O6 133.02(14) 1_455 2_565 ? O2 Pr1 O7 97.88(16) 2_676 . ? O1 Pr1 O7 144.67(14) . . ? O5 Pr1 O7 76.84(15) . . ? O3 Pr1 O7 74.65(14) 2_676 . ? O4 Pr1 O7 110.48(15) 1_455 . ? O6 Pr1 O7 72.06(14) 2_565 . ? O2 Pr1 N1 84.64(15) 2_676 2_675 ? O1 Pr1 N1 75.80(15) . 2_675 ? O5 Pr1 N1 71.01(15) . 2_675 ? O3 Pr1 N1 141.49(15) 2_676 2_675 ? O4 Pr1 N1 82.46(14) 1_455 2_675 ? O6 Pr1 N1 71.33(14) 2_565 2_675 ? O7 Pr1 N1 139.03(15) . 2_675 ? O2 Pr1 O3 140.31(13) 2_676 1_455 ? O1 Pr1 O3 95.47(15) . 1_455 ? O5 Pr1 O3 83.48(13) . 1_455 ? O3 Pr1 O3 71.00(14) 2_676 1_455 ? O4 Pr1 O3 49.91(12) 1_455 1_455 ? O6 Pr1 O3 132.16(13) 2_565 1_455 ? O7 Pr1 O3 66.83(15) . 1_455 ? N1 Pr1 O3 131.50(13) 2_675 1_455 ? O2 Pr1 C8 156.71(15) 2_676 1_455 ? O1 Pr1 C8 86.42(16) . 1_455 ? O5 Pr1 C8 72.92(14) . 1_455 ? O3 Pr1 C8 90.31(14) 2_676 1_455 ? O4 Pr1 C8 24.69(13) 1_455 1_455 ? O6 Pr1 C8 135.22(14) 2_565 1_455 ? O7 Pr1 C8 87.56(16) . 1_455 ? N1 Pr1 C8 106.03(15) 2_675 1_455 ? O3 Pr1 C8 25.57(13) 1_455 1_455 ? C9 O1 Pr1 151.9(4) . . ? C9 O2 Pr1 131.6(3) . 2_676 ? C8 O3 Pr1 133.0(4) . 2_676 ? C8 O3 Pr1 91.9(3) . 1_655 ? Pr1 O3 Pr1 109.00(14) 2_676 1_655 ? C8 O4 Pr1 97.5(3) . 1_655 ? C10 O5 Pr1 119.5(3) . . ? C10 O6 Pr1 117.7(3) . 2_565 ? Pr1 O7 H7A 109.3 . . ? Pr1 O7 H7B 109.2 . . ? H7A O7 H7B 109.5 . . ? C1 N1 C2 104.2(5) . . ? C1 N1 Pr1 121.3(4) . 2_675 ? C2 N1 Pr1 133.7(4) . 2_675 ? C1 N2 C7 107.5(5) . . ? C1 N2 H2A 126.3 . . ? C7 N2 H2A 126.3 . . ? N1 C1 N2 113.7(5) . . ? N1 C1 H1B 123.1 . . ? N2 C1 H1B 123.1 . . ? C3 C2 N1 130.7(5) . . ? C3 C2 C7 119.9(5) . . ? N1 C2 C7 109.3(5) . . ? C2 C3 C4 118.8(5) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C3 C4 C5 120.1(5) . . ? C3 C4 C8 114.8(5) . . ? C5 C4 C8 124.7(5) . . ? C6 C5 C4 120.8(5) . . ? C6 C5 C9 113.4(5) . . ? C4 C5 C9 125.6(5) . . ? C5 C6 C7 118.4(5) . . ? C5 C6 H6A 120.8 . . ? C7 C6 H6A 120.8 . . ? N2 C7 C6 132.8(5) . . ? N2 C7 C2 105.2(5) . . ? C6 C7 C2 121.9(5) . . ? O4 C8 O3 119.1(5) . . ? O4 C8 C4 119.6(5) . . ? O3 C8 C4 121.2(5) . . ? O4 C8 Pr1 57.8(3) . 1_655 ? O3 C8 Pr1 62.6(3) . 1_655 ? C4 C8 Pr1 165.1(4) . 1_655 ? O2 C9 O1 123.0(5) . . ? O2 C9 C5 117.9(5) . . ? O1 C9 C5 118.7(5) . . ? O6 C10 O5 126.2(5) . . ? O6 C10 C10 117.6(6) . 2_565 ? O5 C10 C10 116.2(6) . 2_565 ? HW1A OW1 HW1B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 1.129 _refine_diff_density_min -0.813 _refine_diff_density_rms 0.155