# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_address ; Chemistry Building University of Manchester Brunswick Street Manchester M13 9PL ; _publ_contact_author_email daniel.whittaker@postgrad.manchester.ac.uk _publ_contact_author_phone 01612751405 _publ_contact_author_name 'Daniel Whittaker' _publ_author_name D.M.Whittaker data_xlsn2_0m _database_code_depnum_ccdc_archive 'CCDC 869233' #TrackingRef '- CIF Files.txt' _audit_creation_date 2012-04-22 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H26 Ce N9 O9, C7 H8' _chemical_formula_sum 'C33 H34 Ce N9 O9' _chemical_formula_weight 840.81 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Ce Ce -1.8482 9.6596 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.4789(8) _cell_length_b 15.3507(8) _cell_length_c 16.4216(9) _cell_angle_alpha 90.00 _cell_angle_beta 112.897(3) _cell_angle_gamma 90.00 _cell_volume 3594.5(3) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9883 _cell_measurement_temperature 100.15 _cell_measurement_theta_max 72.200 _cell_measurement_theta_min 3.331 _exptl_absorpt_coefficient_mu 10.347 _exptl_absorpt_correction_T_max 0.7536 _exptl_absorpt_correction_T_min 0.2841 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.1604 before and 0.1049 after correction. The Ratio of minimum to maximum transmission is 0.3770. The \l/2 correction factor is 0.0000. ; _exptl_crystal_colour 'clear yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1700 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.03 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.1200 _diffrn_reflns_av_unetI/netI 0.0705 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 37812 _diffrn_reflns_theta_full 66.55 _diffrn_reflns_theta_max 66.55 _diffrn_reflns_theta_min 3.33 _diffrn_ambient_temperature 100.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_device_type 'Bruker SMART APEX-2 CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'micro-focus sealed tube' _diffrn_source_current 0.65 _diffrn_source_power 0.02925 _diffrn_source_voltage 45.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4468 _reflns_number_total 6199 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 3.075 _refine_diff_density_min -0.977 _refine_diff_density_rms 0.135 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 487 _refine_ls_number_reflns 6199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1029 _refine_ls_R_factor_gt 0.0690 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+39.5366P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1562 _refine_ls_wR_factor_ref 0.1827 _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. All residual electron density within the structure is located around the central Ce ion. All atoms, except hydrogen, were refined anisotropically. The modelled disorder within the structure was done by parts isotropically and then made anisotropic before hydrogen atoms were added. C52B and C53B have had the EADP restraint applied. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Ce1 Ce 0.57339(3) 0.20948(3) 0.16102(3) 0.03735(18) Uani 1 1 d . . . N31 N 0.5715(5) 0.3787(5) 0.1457(5) 0.0345(16) Uani 1 1 d . . . O7 O 0.6531(5) 0.2892(4) 0.3124(4) 0.0479(16) Uani 1 1 d . . . N41 N 0.4174(5) 0.2929(5) 0.1322(5) 0.0412(18) Uani 1 1 d . . . O2 O 0.4646(5) 0.1352(4) 0.0193(5) 0.0545(18) Uani 1 1 d . . . N21 N 0.7243(5) 0.2819(5) 0.1553(5) 0.0408(18) Uani 1 1 d . . . N9 N 0.7096(6) 0.2273(5) 0.3501(5) 0.046(2) Uani 1 1 d . . . O3 O 0.4250(6) 0.1890(6) -0.1127(5) 0.074(2) Uani 1 1 d . . . O9 O 0.7628(5) 0.2308(5) 0.4274(4) 0.0578(19) Uani 1 1 d . . . O5 O 0.5044(5) 0.1576(5) 0.2724(5) 0.0550(18) Uani 1 1 d . . . O1 O 0.5221(5) 0.2591(5) 0.0010(4) 0.0513(18) Uani 1 1 d . . . C44 C 0.2620(7) 0.2871(7) 0.1105(6) 0.048(2) Uani 1 1 d . A . C36 C 0.4935(7) 0.4289(6) 0.1220(6) 0.044(2) Uani 1 1 d . . . O4 O 0.5249(5) 0.0581(5) 0.1893(4) 0.0489(16) Uani 1 1 d . . . C34 C 0.5711(7) 0.5609(7) 0.1148(6) 0.050(3) Uani 1 1 d . . . H34 H 0.5713 0.6220 0.1057 0.060 Uiso 1 1 calc R . . N8 N 0.4931(6) 0.0782(6) 0.2453(6) 0.050(2) Uani 1 1 d . . . C22 C 0.7984(7) 0.2317(7) 0.1642(6) 0.044(2) Uani 1 1 d . . . N45 N 0.3279(6) 0.4227(5) 0.0920(5) 0.046(2) Uani 1 1 d . . . N7 N 0.4696(6) 0.1952(6) -0.0344(5) 0.054(2) Uani 1 1 d . . . N11 N 0.6899(5) 0.1111(5) 0.1233(5) 0.0407(18) Uani 1 1 d . . . N42 N 0.3437(5) 0.2478(5) 0.1301(5) 0.0454(19) Uani 1 1 d . . . C16 C 0.7790(6) 0.1359(7) 0.1447(6) 0.044(2) Uani 1 1 d . . . O6 O 0.4510(6) 0.0266(6) 0.2748(6) 0.075(2) Uani 1 1 d . . . C23 C 0.8879(7) 0.2660(7) 0.1895(7) 0.053(3) Uani 1 1 d . . . H23 H 0.9394 0.2293 0.1955 0.064 Uiso 1 1 calc R . . C26 C 0.7370(7) 0.3689(6) 0.1679(6) 0.046(2) Uani 1 1 d . . . C13 C 0.7341(7) -0.0342(7) 0.0994(7) 0.050(2) Uani 1 1 d . . . H13 H 0.7163 -0.0931 0.0839 0.061 Uiso 1 1 calc R . . C33 C 0.6522(8) 0.5123(6) 0.1340(7) 0.049(2) Uani 1 1 d . . . H33 H 0.7086 0.5398 0.1377 0.059 Uiso 1 1 calc R . . C14 C 0.8250(8) -0.0076(8) 0.1210(7) 0.058(3) Uani 1 1 d . . . H14 H 0.8716 -0.0478 0.1210 0.070 Uiso 1 1 calc R . . C43 C 0.2540(7) 0.3777(7) 0.0883(7) 0.052(3) Uani 1 1 d . A . C25 C 0.8251(7) 0.4063(7) 0.1951(7) 0.052(3) Uani 1 1 d . . . H25 H 0.8329 0.4671 0.2060 0.062 Uiso 1 1 calc R . . C35 C 0.4895(8) 0.5189(7) 0.1092(6) 0.052(3) Uani 1 1 d . . . H35 H 0.4330 0.5504 0.0970 0.063 Uiso 1 1 calc R . . C15 C 0.8476(7) 0.0784(7) 0.1425(7) 0.050(3) Uani 1 1 d . . . H15 H 0.9097 0.0984 0.1558 0.060 Uiso 1 1 calc R . . C32 C 0.6505(7) 0.4218(6) 0.1480(6) 0.043(2) Uani 1 1 d . . . C12 C 0.6689(7) 0.0273(6) 0.1009(6) 0.044(2) Uani 1 1 d . . . H12 H 0.6058 0.0090 0.0851 0.053 Uiso 1 1 calc R . . C46 C 0.4083(7) 0.3783(6) 0.1155(6) 0.044(2) Uani 1 1 d . . . C24 C 0.9012(7) 0.3546(7) 0.2060(7) 0.056(3) Uani 1 1 d . . . H24 H 0.9622 0.3792 0.2247 0.067 Uiso 1 1 calc R . . O8 O 0.7081(5) 0.1611(4) 0.3011(4) 0.0485(17) Uani 1 1 d . . . C51 C 0.1603(8) 0.4254(8) 0.0558(9) 0.066(3) Uani 1 1 d . . . C54 C 0.1816(7) 0.2320(8) 0.1125(7) 0.052(3) Uani 1 1 d . . . C55 C 0.2098(9) 0.1886(9) 0.2025(8) 0.072(4) Uani 1 1 d . A . H55A H 0.2664 0.1534 0.2146 0.107 Uiso 1 1 calc R . . H55B H 0.1587 0.1510 0.2027 0.107 Uiso 1 1 calc R . . H55C H 0.2226 0.2334 0.2483 0.107 Uiso 1 1 calc R . . C53A C 0.0989(12) 0.2946(17) 0.1062(16) 0.058(7) Uani 0.70(4) 1 d P A 1 H53A H 0.0416 0.2597 0.0952 0.070 Uiso 0.70(4) 1 calc PR A 1 H53B H 0.1150 0.3254 0.1632 0.070 Uiso 0.70(4) 1 calc PR A 1 C56 C 0.1599(10) 0.1616(9) 0.0416(9) 0.083(4) Uani 1 1 d . A . H56A H 0.1502 0.1886 -0.0153 0.124 Uiso 1 1 calc R . . H56B H 0.1029 0.1302 0.0369 0.124 Uiso 1 1 calc R . . H56C H 0.2125 0.1206 0.0578 0.124 Uiso 1 1 calc R . . C58 C 0.1458(9) 0.4674(9) -0.0331(8) 0.080(4) Uani 1 1 d . A . H58A H 0.1984 0.5063 -0.0258 0.119 Uiso 1 1 calc R . . H58B H 0.0872 0.5008 -0.0544 0.119 Uiso 1 1 calc R . . H58C H 0.1423 0.4218 -0.0761 0.119 Uiso 1 1 calc R . . C57 C 0.1707(10) 0.4984(10) 0.1211(9) 0.089(5) Uani 1 1 d . A . H57A H 0.1881 0.4740 0.1805 0.133 Uiso 1 1 calc R . . H57B H 0.1111 0.5297 0.1042 0.133 Uiso 1 1 calc R . . H57C H 0.2197 0.5388 0.1208 0.133 Uiso 1 1 calc R . . C52A C 0.0790(11) 0.3615(14) 0.0322(15) 0.063(7) Uani 0.70(4) 1 d P A 1 H52A H 0.0704 0.3313 -0.0237 0.075 Uiso 0.70(4) 1 calc PR A 1 H52B H 0.0205 0.3934 0.0235 0.075 Uiso 0.70(4) 1 calc PR A 1 C61 C 0.3372(10) 0.3682(12) 0.3799(8) 0.084(4) Uani 1 1 d . . . C65 C 0.1865(10) 0.3710(11) 0.3925(8) 0.079(4) Uani 1 1 d . . . H65 H 0.1286 0.3996 0.3820 0.095 Uiso 1 1 calc R . . C62 C 0.3525(11) 0.2877(12) 0.4177(9) 0.090(5) Uani 1 1 d . . . H62 H 0.4102 0.2593 0.4274 0.108 Uiso 1 1 calc R . . C66 C 0.2534(11) 0.4101(10) 0.3689(9) 0.082(4) Uani 1 1 d . . . H66 H 0.2422 0.4671 0.3444 0.099 Uiso 1 1 calc R . . C64 C 0.2046(13) 0.2896(12) 0.4318(9) 0.096(5) Uani 1 1 d . . . H64 H 0.1608 0.2631 0.4516 0.115 Uiso 1 1 calc R . . C63 C 0.2888(14) 0.2460(12) 0.4423(9) 0.099(5) Uani 1 1 d . . . H63 H 0.3007 0.1888 0.4660 0.119 Uiso 1 1 calc R . . C67 C 0.4091(12) 0.4120(16) 0.3487(11) 0.130(8) Uani 1 1 d . . . H67A H 0.4557 0.4437 0.3982 0.195 Uiso 1 1 calc R . . H67B H 0.3765 0.4528 0.3006 0.195 Uiso 1 1 calc R . . H67C H 0.4406 0.3673 0.3276 0.195 Uiso 1 1 calc R . . C52B C 0.093(3) 0.375(4) 0.098(4) 0.076(17) Uani 0.30(4) 1 d P A 2 H52C H 0.1190 0.3793 0.1634 0.091 Uiso 0.30(4) 1 calc PR A 2 H52D H 0.0283 0.3982 0.0741 0.091 Uiso 0.30(4) 1 calc PR A 2 C53B C 0.095(4) 0.278(4) 0.068(4) 0.076(17) Uani 0.30(4) 1 d P A 2 H53C H 0.0442 0.2454 0.0763 0.091 Uiso 0.30(4) 1 calc PR A 2 H53D H 0.0816 0.2782 0.0037 0.091 Uiso 0.30(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ce1 0.0335(3) 0.0267(3) 0.0424(3) 0.0023(2) 0.0045(2) 0.0018(2) N31 0.028(4) 0.028(4) 0.045(4) -0.007(3) 0.010(3) 0.001(3) O7 0.049(4) 0.035(4) 0.046(4) 0.000(3) 0.004(3) 0.006(3) N41 0.032(4) 0.032(5) 0.050(4) 0.002(4) 0.006(3) 0.009(3) O2 0.054(4) 0.031(4) 0.059(4) 0.002(3) 0.001(3) -0.004(3) N21 0.040(4) 0.035(5) 0.043(4) 0.000(3) 0.011(3) -0.001(3) N9 0.044(5) 0.043(5) 0.039(4) 0.001(4) 0.003(4) 0.000(4) O3 0.084(6) 0.075(6) 0.042(4) -0.006(4) 0.003(4) -0.008(5) O9 0.050(4) 0.062(5) 0.041(4) 0.001(3) -0.005(3) -0.002(3) O5 0.048(4) 0.053(5) 0.052(4) 0.001(3) 0.007(3) 0.008(3) O1 0.057(4) 0.038(4) 0.044(4) 0.001(3) 0.004(3) -0.003(3) C44 0.043(5) 0.045(6) 0.044(5) -0.002(5) 0.005(4) 0.005(5) C36 0.047(6) 0.029(5) 0.040(5) 0.003(4) 0.001(4) 0.000(4) O4 0.054(4) 0.043(4) 0.050(4) 0.005(3) 0.021(3) -0.003(3) C34 0.058(6) 0.034(6) 0.044(5) 0.003(4) 0.005(5) -0.002(5) N8 0.035(4) 0.052(6) 0.055(5) 0.013(4) 0.007(4) 0.002(4) C22 0.039(5) 0.042(6) 0.042(5) -0.002(4) 0.006(4) -0.007(4) N45 0.047(5) 0.038(5) 0.045(4) 0.007(4) 0.009(4) 0.010(4) N7 0.051(5) 0.052(6) 0.043(5) -0.004(4) 0.003(4) 0.001(4) N11 0.042(4) 0.029(5) 0.045(4) 0.002(3) 0.010(4) 0.002(3) N42 0.036(4) 0.038(5) 0.050(5) 0.002(4) 0.003(4) -0.001(3) C16 0.036(5) 0.045(6) 0.039(5) -0.003(4) 0.003(4) -0.004(4) O6 0.066(5) 0.076(6) 0.087(6) 0.004(5) 0.035(5) -0.017(4) C23 0.037(5) 0.048(7) 0.066(7) 0.000(5) 0.012(5) -0.002(4) C26 0.050(6) 0.028(6) 0.048(5) -0.005(4) 0.006(4) -0.003(4) C13 0.057(6) 0.030(6) 0.057(6) -0.003(4) 0.014(5) 0.004(4) C33 0.059(6) 0.029(6) 0.055(6) -0.005(4) 0.018(5) -0.011(4) C14 0.048(6) 0.056(8) 0.063(7) -0.009(6) 0.013(5) 0.007(5) C43 0.047(6) 0.046(7) 0.060(6) 0.002(5) 0.018(5) 0.014(5) C25 0.051(6) 0.033(6) 0.061(6) -0.005(5) 0.011(5) -0.012(4) C35 0.056(6) 0.037(6) 0.048(6) 0.008(5) 0.005(5) 0.007(5) C15 0.034(5) 0.054(7) 0.060(6) -0.003(5) 0.015(5) 0.004(4) C32 0.056(6) 0.023(5) 0.039(5) -0.003(4) 0.008(4) -0.003(4) C12 0.048(6) 0.034(6) 0.048(5) -0.004(4) 0.015(4) -0.002(4) C46 0.044(5) 0.037(6) 0.044(5) -0.002(4) 0.008(4) 0.005(4) C24 0.032(5) 0.057(7) 0.062(7) 0.000(5) 0.000(5) -0.012(5) O8 0.044(4) 0.042(4) 0.048(4) 0.002(3) 0.005(3) 0.007(3) C51 0.050(7) 0.058(8) 0.086(9) 0.010(6) 0.022(6) 0.026(6) C54 0.035(5) 0.066(8) 0.052(6) 0.000(5) 0.013(4) 0.002(5) C55 0.065(8) 0.083(10) 0.060(7) 0.013(6) 0.017(6) -0.010(6) C53A 0.037(8) 0.076(18) 0.074(12) 0.017(12) 0.035(9) 0.012(9) C56 0.092(10) 0.085(10) 0.078(9) -0.029(8) 0.040(8) -0.047(8) C58 0.071(8) 0.091(11) 0.062(7) -0.004(7) 0.009(6) 0.047(8) C57 0.089(10) 0.101(12) 0.073(8) 0.013(8) 0.029(7) 0.063(9) C52A 0.039(9) 0.074(15) 0.076(15) 0.014(11) 0.024(8) 0.015(8) C61 0.067(9) 0.119(13) 0.049(7) 0.001(8) 0.006(6) -0.001(9) C65 0.078(9) 0.098(12) 0.049(7) -0.006(7) 0.010(6) 0.012(8) C62 0.077(10) 0.119(14) 0.055(7) 0.014(9) 0.004(7) 0.025(9) C66 0.085(10) 0.078(10) 0.063(8) 0.006(7) 0.006(7) 0.006(8) C64 0.122(14) 0.105(14) 0.058(8) -0.012(8) 0.033(9) -0.011(11) C63 0.140(16) 0.101(13) 0.046(7) 0.002(7) 0.026(9) 0.027(12) C67 0.094(13) 0.20(2) 0.087(12) 0.011(13) 0.027(10) -0.037(14) C52B 0.061(19) 0.09(4) 0.09(3) -0.05(3) 0.048(19) -0.004(17) C53B 0.061(19) 0.09(4) 0.09(3) -0.05(3) 0.048(19) -0.004(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 Ce1 N31 2.609(7) . ? Ce1 O7 2.609(6) . ? Ce1 N41 2.608(7) . ? Ce1 O2 2.550(7) . ? Ce1 N21 2.621(8) . ? Ce1 O5 2.577(8) . ? Ce1 O1 2.548(7) . ? Ce1 O4 2.540(7) . ? Ce1 N11 2.605(8) . ? Ce1 O8 2.541(6) . ? N31 C36 1.356(12) . ? N31 C32 1.378(12) . ? O7 N9 1.276(10) . ? N41 N42 1.324(11) . ? N41 C46 1.337(12) . ? O2 N7 1.298(11) . ? N21 C22 1.341(12) . ? N21 C26 1.354(12) . ? N9 O9 1.217(10) . ? N9 O8 1.291(10) . ? O3 N7 1.203(10) . ? O5 N8 1.286(11) . ? O1 N7 1.262(11) . ? C44 N42 1.322(12) . ? C44 C43 1.431(15) . ? C44 C54 1.515(14) . ? C36 C35 1.395(14) . ? C36 C46 1.497(14) . ? O4 N8 1.239(11) . ? C34 C33 1.388(14) . ? C34 C35 1.388(15) . ? N8 O6 1.239(11) . ? C22 C16 1.510(14) . ? C22 C23 1.386(13) . ? N45 C43 1.318(13) . ? N45 C46 1.337(12) . ? N11 C16 1.340(12) . ? N11 C12 1.342(12) . ? C16 C15 1.392(14) . ? C23 C24 1.386(16) . ? C26 C25 1.384(13) . ? C26 C32 1.489(14) . ? C13 C14 1.373(15) . ? C13 C12 1.390(14) . ? C33 C32 1.410(14) . ? C14 C15 1.375(15) . ? C43 C51 1.524(14) . ? C25 C24 1.373(15) . ? C51 C58 1.530(17) . ? C51 C57 1.516(18) . ? C51 C52A 1.52(2) . ? C51 C52B 1.66(5) . ? C54 C55 1.523(15) . ? C54 C53A 1.57(2) . ? C54 C56 1.527(16) . ? C54 C53B 1.44(6) . ? C53A C52A 1.53(3) . ? C61 C62 1.36(2) . ? C61 C66 1.40(2) . ? C61 C67 1.55(2) . ? C65 C66 1.38(2) . ? C65 C64 1.38(2) . ? C62 C63 1.36(2) . ? C64 C63 1.41(2) . ? C52B C53B 1.57(8) . ? 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 N31 Ce1 N21 63.3(2) . . ? O7 Ce1 N31 67.0(2) . . ? O7 Ce1 N21 74.8(2) . . ? N41 Ce1 N31 61.2(2) . . ? N41 Ce1 O7 90.2(2) . . ? N41 Ce1 N21 124.1(2) . . ? O2 Ce1 N31 112.2(2) . . ? O2 Ce1 O7 168.1(2) . . ? O2 Ce1 N41 79.5(2) . . ? O2 Ce1 N21 116.0(2) . . ? O2 Ce1 O5 101.6(2) . . ? O2 Ce1 N11 78.3(2) . . ? O5 Ce1 N31 112.6(2) . . ? O5 Ce1 O7 69.0(2) . . ? O5 Ce1 N41 70.8(2) . . ? O5 Ce1 N21 141.0(2) . . ? O5 Ce1 N11 120.4(2) . . ? O1 Ce1 N31 67.4(2) . . ? O1 Ce1 O7 133.2(2) . . ? O1 Ce1 N41 76.8(2) . . ? O1 Ce1 O2 50.4(2) . . ? O1 Ce1 N21 76.1(2) . . ? O1 Ce1 O5 140.9(2) . . ? O1 Ce1 N11 84.0(2) . . ? O4 Ce1 N31 159.3(2) . . ? O4 Ce1 O7 108.6(2) . . ? O4 Ce1 N41 99.4(2) . . ? O4 Ce1 O2 67.7(2) . . ? O4 Ce1 N21 136.5(2) . . ? O4 Ce1 O5 49.8(2) . . ? O4 Ce1 O1 117.8(2) . . ? O4 Ce1 N11 78.1(2) . . ? O4 Ce1 O8 76.4(2) . . ? N11 Ce1 N31 122.5(2) . . ? N11 Ce1 O7 112.6(2) . . ? N11 Ce1 N41 156.8(2) . . ? N11 Ce1 N21 61.9(2) . . ? O8 Ce1 N31 110.7(2) . . ? O8 Ce1 O7 50.0(2) . . ? O8 Ce1 N41 133.1(2) . . ? O8 Ce1 O2 135.5(2) . . ? O8 Ce1 N21 74.2(2) . . ? O8 Ce1 O5 71.8(2) . . ? O8 Ce1 O1 146.9(2) . . ? O8 Ce1 N11 69.2(2) . . ? C36 N31 Ce1 124.7(6) . . ? C36 N31 C32 114.7(8) . . ? C32 N31 Ce1 119.9(6) . . ? N9 O7 Ce1 95.4(5) . . ? N42 N41 Ce1 118.4(6) . . ? N42 N41 C46 119.1(8) . . ? C46 N41 Ce1 122.4(6) . . ? N7 O2 Ce1 96.3(5) . . ? C22 N21 Ce1 119.3(6) . . ? C22 N21 C26 118.8(8) . . ? C26 N21 Ce1 119.4(6) . . ? O7 N9 O8 116.1(7) . . ? O9 N9 O7 122.1(8) . . ? O9 N9 O8 121.7(8) . . ? N8 O5 Ce1 94.9(6) . . ? N7 O1 Ce1 97.4(6) . . ? N42 C44 C43 119.0(10) . . ? N42 C44 C54 117.1(10) . . ? C43 C44 C54 123.9(9) . . ? N31 C36 C35 126.0(10) . . ? N31 C36 C46 112.8(8) . . ? C35 C36 C46 121.2(9) . . ? N8 O4 Ce1 98.0(6) . . ? C33 C34 C35 119.0(10) . . ? O4 N8 O5 117.0(8) . . ? O4 N8 O6 123.6(10) . . ? O6 N8 O5 119.4(10) . . ? N21 C22 C16 116.5(8) . . ? N21 C22 C23 121.9(10) . . ? C23 C22 C16 121.7(9) . . ? C43 N45 C46 116.1(9) . . ? O3 N7 O2 120.6(9) . . ? O3 N7 O1 123.5(10) . . ? O1 N7 O2 115.9(8) . . ? C16 N11 Ce1 120.7(6) . . ? C16 N11 C12 117.4(8) . . ? C12 N11 Ce1 120.3(6) . . ? C44 N42 N41 120.0(9) . . ? N11 C16 C22 115.6(9) . . ? N11 C16 C15 122.0(9) . . ? C15 C16 C22 122.3(9) . . ? C22 C23 C24 119.1(10) . . ? N21 C26 C25 121.6(9) . . ? N21 C26 C32 116.1(8) . . ? C25 C26 C32 122.3(9) . . ? C14 C13 C12 118.1(10) . . ? C34 C33 C32 119.6(10) . . ? C13 C14 C15 119.0(10) . . ? C44 C43 C51 122.1(10) . . ? N45 C43 C44 120.8(9) . . ? N45 C43 C51 117.0(10) . . ? C24 C25 C26 119.4(10) . . ? C34 C35 C36 117.7(10) . . ? C14 C15 C16 119.7(10) . . ? N31 C32 C26 117.2(8) . . ? N31 C32 C33 122.7(9) . . ? C33 C32 C26 120.1(9) . . ? N11 C12 C13 123.8(9) . . ? N41 C46 C36 118.4(8) . . ? N41 C46 N45 124.8(9) . . ? N45 C46 C36 116.8(9) . . ? C25 C24 C23 119.1(9) . . ? N9 O8 Ce1 98.3(5) . . ? C43 C51 C58 107.6(10) . . ? C43 C51 C52B 107(2) . . ? C58 C51 C52B 136(2) . . ? C57 C51 C43 106.5(10) . . ? C57 C51 C58 107.4(11) . . ? C57 C51 C52A 120.4(13) . . ? C57 C51 C52B 87.8(18) . . ? C52A C51 C43 111.0(11) . . ? C52A C51 C58 103.2(13) . . ? C52A C51 C52B 37.9(16) . . ? C44 C54 C55 109.7(9) . . ? C44 C54 C53A 108.2(11) . . ? C44 C54 C56 108.5(9) . . ? C55 C54 C53A 104.5(11) . . ? C55 C54 C56 108.9(11) . . ? C56 C54 C53A 116.8(13) . . ? C53B C54 C44 109(3) . . ? C53B C54 C55 125(3) . . ? C53B C54 C53A 24.9(18) . . ? C53B C54 C56 94(2) . . ? C52A C53A C54 111.7(16) . . ? C51 C52A C53A 109.9(16) . . ? C62 C61 C66 117.8(15) . . ? C62 C61 C67 121.7(16) . . ? C66 C61 C67 120.6(17) . . ? C66 C65 C64 119.1(15) . . ? C63 C62 C61 122.9(16) . . ? C65 C66 C61 121.7(15) . . ? C65 C64 C63 119.6(17) . . ? C62 C63 C64 118.8(17) . . ? C53B C52B C51 102(4) . . ? C54 C53B C52B 116(4) . . ? #===END data_xlsn3_0m _database_code_depnum_ccdc_archive 'CCDC 869234' #TrackingRef '- CIF Files.txt' _audit_creation_date 2012-04-18 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H26 Eu N9 O9, 2(C2 H3 N)' _chemical_formula_sum 'C30 H32 Eu N11 O9' _chemical_formula_weight 842.63 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -8.9294 11.1857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 12.8212(3) _cell_length_b 14.9805(4) _cell_length_c 18.2654(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.155(2) _cell_angle_gamma 90.00 _cell_volume 3429.55(15) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9874 _cell_measurement_temperature 100.15 _cell_measurement_theta_max 70.125 _cell_measurement_theta_min 3.527 _exptl_absorpt_coefficient_mu 13.688 _exptl_absorpt_correction_T_max 0.7533 _exptl_absorpt_correction_T_min 0.3146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. R(int) was 0.1549 before and 0.0966 after correction. The Ratio of minimum to maximum transmission is 0.4176. The \l/2 correction factor is 0.0000. ; _exptl_crystal_colour 'clear yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1696 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.03 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0764 _diffrn_reflns_av_unetI/netI 0.0480 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 54007 _diffrn_reflns_theta_full 70.07 _diffrn_reflns_theta_max 70.07 _diffrn_reflns_theta_min 3.53 _diffrn_ambient_temperature 100.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 0.65 _diffrn_source_power 0.02925 _diffrn_source_voltage 45.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5561 _reflns_number_total 6504 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 1.657 _refine_diff_density_min -1.327 _refine_diff_density_rms 0.135 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 430 _refine_ls_number_reflns 6504 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0458 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1047P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1343 _refine_ls_wR_factor_ref 0.1417 _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. All non-hydrogen atoms were refined anisotropically. Hydrogen atoms were placed in fixed positions. Solvent CH3CN (C63 C62 N61 C73 C72 N71) molecules had the EADP constraint applied. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O4 O 0.3110(3) 0.5646(2) 0.0907(2) 0.0288(8) Uani 1 1 d . . . O5 O 0.2098(3) 0.6733(2) 0.1091(2) 0.0281(8) Uani 1 1 d . . . O6 O 0.1406(3) 0.5419(3) 0.0800(2) 0.0439(10) Uani 1 1 d . . . O8 O 0.3305(3) 0.7950(2) 0.2094(2) 0.0247(7) Uani 1 1 d . . . O9 O 0.3284(3) 0.7362(3) 0.3187(2) 0.0327(8) Uani 1 1 d . . . O7 O 0.3926(2) 0.6623(2) 0.23522(19) 0.0215(7) Uani 1 1 d . . . O2 O 0.4320(3) 0.6301(2) -0.00463(19) 0.0277(8) Uani 1 1 d . . . O3 O 0.5406(3) 0.6743(3) -0.0742(2) 0.0427(10) Uani 1 1 d . . . O1 O 0.5193(3) 0.7530(2) 0.0209(2) 0.0270(8) Uani 1 1 d . . . N2 N 0.2176(3) 0.5913(3) 0.0930(2) 0.0280(9) Uani 1 1 d . . . N11 N 0.5569(3) 0.6158(3) 0.1621(2) 0.0203(8) Uani 1 1 d . . . N21 N 0.5560(3) 0.7907(2) 0.1912(2) 0.0191(8) Uani 1 1 d . . . N31 N 0.4146(3) 0.8835(2) 0.0908(2) 0.0175(7) Uani 1 1 d . . . N45 N 0.2144(3) 0.9103(3) -0.0790(2) 0.0256(9) Uani 1 1 d . . . N42 N 0.2015(3) 0.7320(3) -0.0447(3) 0.0252(9) Uani 1 1 d . . . N41 N 0.2735(3) 0.7856(2) -0.0021(3) 0.0227(9) Uani 1 1 d . . . N3 N 0.3494(3) 0.7325(3) 0.2565(3) 0.0237(9) Uani 1 1 d . . . N1 N 0.4988(3) 0.6854(3) -0.0212(3) 0.0268(9) Uani 1 1 d . . . C16 C 0.6254(3) 0.6435(3) 0.2253(3) 0.0205(9) Uani 1 1 d . . . C22 C 0.6229(3) 0.7402(3) 0.2415(3) 0.0189(9) Uani 1 1 d . . . C26 C 0.5571(3) 0.8797(3) 0.1995(3) 0.0199(9) Uani 1 1 d . . . C25 C 0.6215(3) 0.9221(3) 0.2612(3) 0.0233(10) Uani 1 1 d . . . H25 H 0.6204 0.9852 0.2662 0.028 Uiso 1 1 calc R . . C24 C 0.6866(3) 0.8702(3) 0.3147(3) 0.0254(10) Uani 1 1 d . . . H56 H 0.7300 0.8972 0.3576 0.030 Uiso 1 1 calc R . . C23 C 0.6881(4) 0.7788(3) 0.3052(3) 0.0243(11) Uani 1 1 d . . . H23 H 0.7327 0.7423 0.3413 0.029 Uiso 1 1 calc R . . C32 C 0.4884(3) 0.9322(3) 0.1389(3) 0.0198(9) Uani 1 1 d . . . C36 C 0.3530(3) 0.9284(3) 0.0328(3) 0.0209(9) Uani 1 1 d . . . C35 C 0.3594(4) 1.0193(3) 0.0213(3) 0.0256(10) Uani 1 1 d . . . H35 H 0.3137 1.0480 -0.0196 0.031 Uiso 1 1 calc R . . C34 C 0.4346(4) 1.0669(3) 0.0715(3) 0.0278(11) Uani 1 1 d . . . H34 H 0.4407 1.1296 0.0659 0.033 Uiso 1 1 calc R . . C33 C 0.5010(4) 1.0235(3) 0.1299(3) 0.0252(10) Uani 1 1 d . . . H33 H 0.5546 1.0555 0.1635 0.030 Uiso 1 1 calc R . . C46 C 0.2763(4) 0.8720(3) -0.0189(3) 0.0226(10) Uani 1 1 d . . . C43 C 0.1455(4) 0.8589(4) -0.1232(3) 0.0279(10) Uani 1 1 d . . . C51 C 0.0800(4) 0.9006(5) -0.1936(4) 0.0434(15) Uani 1 1 d . . . C58 C 0.1513(5) 0.9587(4) -0.2322(3) 0.0413(14) Uani 1 1 d . . . H58A H 0.1840 1.0061 -0.1979 0.062 Uiso 1 1 calc R . . H58B H 0.1081 0.9854 -0.2775 0.062 Uiso 1 1 calc R . . H58C H 0.2074 0.9216 -0.2456 0.062 Uiso 1 1 calc R . . C57 C -0.0012(5) 0.9606(6) -0.1677(5) 0.075(3) Uani 1 1 d . . . H57A H -0.0460 0.9245 -0.1418 0.113 Uiso 1 1 calc R . . H57B H -0.0461 0.9896 -0.2113 0.113 Uiso 1 1 calc R . . H57C H 0.0363 1.0061 -0.1335 0.113 Uiso 1 1 calc R . . C52 C 0.0281(6) 0.8270(6) -0.2469(4) 0.076(3) Uani 1 1 d . . . H52A H -0.0254 0.8540 -0.2879 0.091 Uiso 1 1 calc R . . H52B H 0.0833 0.7982 -0.2695 0.091 Uiso 1 1 calc R . . C53 C -0.0255(5) 0.7569(6) -0.2081(4) 0.062(2) Uani 1 1 d . . . H53A H -0.0642 0.7148 -0.2461 0.074 Uiso 1 1 calc R . . H53B H -0.0786 0.7863 -0.1839 0.074 Uiso 1 1 calc R . . C54 C 0.0544(4) 0.7033(4) -0.1477(4) 0.0336(13) Uani 1 1 d . . . C55 C -0.0062(4) 0.6553(4) -0.0977(3) 0.0397(14) Uani 1 1 d . . . H55A H -0.0441 0.6988 -0.0728 0.060 Uiso 1 1 calc R . . H55B H 0.0437 0.6213 -0.0598 0.060 Uiso 1 1 calc R . . H55C H -0.0578 0.6143 -0.1277 0.060 Uiso 1 1 calc R . . C56 C 0.1162(5) 0.6349(6) -0.1846(6) 0.086(3) Uani 1 1 d . . . H56A H 0.0659 0.5931 -0.2147 0.129 Uiso 1 1 calc R . . H56B H 0.1655 0.6019 -0.1457 0.129 Uiso 1 1 calc R . . H56C H 0.1565 0.6659 -0.2169 0.129 Uiso 1 1 calc R . . C44 C 0.1357(4) 0.7672(4) -0.1037(3) 0.0239(10) Uani 1 1 d . . . C15 C 0.6943(3) 0.5846(3) 0.2702(3) 0.0242(10) Uani 1 1 d . . . H15 H 0.7404 0.6051 0.3147 0.029 Uiso 1 1 calc R . . C14 C 0.6952(4) 0.4962(3) 0.2495(3) 0.0271(10) Uani 1 1 d . . . H14 H 0.7419 0.4551 0.2797 0.032 Uiso 1 1 calc R . . C13 C 0.6273(4) 0.4679(3) 0.1841(3) 0.0248(10) Uani 1 1 d . . . H13 H 0.6273 0.4075 0.1683 0.030 Uiso 1 1 calc R . . C12 C 0.5595(4) 0.5298(3) 0.1426(3) 0.0217(9) Uani 1 1 d . . . H12 H 0.5125 0.5104 0.0981 0.026 Uiso 1 1 calc R . . N61 N 0.1399(6) 1.1373(7) 0.0410(4) 0.0952(14) Uani 1 1 d . . . C62 C 0.0682(7) 1.1513(9) -0.0097(6) 0.0952(14) Uani 1 1 d . . . C63 C -0.0213(7) 1.1750(8) -0.0736(6) 0.0952(14) Uani 1 1 d . . . H63A H 0.0006 1.1640 -0.1211 0.143 Uiso 1 1 calc R . . H63B H -0.0393 1.2383 -0.0703 0.143 Uiso 1 1 calc R . . H63C H -0.0839 1.1384 -0.0713 0.143 Uiso 1 1 calc R . . C72 C 0.7847(8) 0.6807(9) 0.0879(6) 0.0952(14) Uani 1 1 d . . . N71 N 0.7907(6) 0.7543(8) 0.1210(5) 0.0952(14) Uani 1 1 d . . . C73 C 0.7719(7) 0.6049(8) 0.0430(5) 0.0952(14) Uani 1 1 d . . . H73A H 0.7554 0.6226 -0.0098 0.143 Uiso 1 1 calc R . . H73B H 0.7132 0.5687 0.0538 0.143 Uiso 1 1 calc R . . H73C H 0.8379 0.5698 0.0534 0.143 Uiso 1 1 calc R . . Eu1 Eu 0.400235(18) 0.714299(16) 0.107079(14) 0.01585(12) 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 O4 0.0318(17) 0.0183(16) 0.033(2) 0.0008(15) -0.0003(16) -0.0075(14) O5 0.0235(15) 0.0238(17) 0.032(2) 0.0035(15) -0.0047(15) -0.0058(13) O6 0.038(2) 0.043(2) 0.046(2) 0.005(2) 0.0000(19) -0.0261(18) O8 0.0269(17) 0.0145(16) 0.033(2) 0.0024(14) 0.0082(16) 0.0007(12) O9 0.038(2) 0.0341(19) 0.030(2) -0.0028(17) 0.0163(18) -0.0044(16) O7 0.0217(14) 0.0176(16) 0.0249(17) 0.0035(13) 0.0040(13) 0.0029(12) O2 0.0391(19) 0.0193(17) 0.0243(18) -0.0026(14) 0.0061(16) -0.0033(14) O3 0.053(2) 0.047(3) 0.033(2) -0.0066(19) 0.021(2) -0.002(2) O1 0.0358(18) 0.0205(18) 0.0265(19) -0.0042(15) 0.0106(16) -0.0056(14) N2 0.028(2) 0.025(2) 0.026(2) 0.0048(18) -0.0041(18) -0.0161(17) N11 0.0180(16) 0.0208(19) 0.021(2) -0.0021(16) 0.0009(15) 0.0001(14) N21 0.0188(18) 0.0150(19) 0.024(2) -0.0005(15) 0.0051(16) -0.0011(13) N31 0.0216(16) 0.0108(17) 0.0196(19) -0.0014(15) 0.0029(16) -0.0005(13) N45 0.0268(19) 0.021(2) 0.027(2) 0.0060(17) 0.0029(17) 0.0034(16) N42 0.0224(19) 0.024(2) 0.027(2) -0.0027(18) 0.0002(18) -0.0053(16) N41 0.023(2) 0.018(2) 0.024(2) 0.0000(15) -0.0011(18) -0.0011(14) N3 0.0227(19) 0.0208(19) 0.028(2) -0.0044(18) 0.0074(18) -0.0064(16) N1 0.033(2) 0.021(2) 0.027(2) 0.0007(18) 0.0072(19) 0.0031(18) C16 0.0195(19) 0.020(2) 0.023(2) -0.0022(19) 0.0059(18) 0.0007(17) C22 0.0154(19) 0.019(2) 0.023(2) -0.0010(19) 0.0045(18) -0.0025(16) C26 0.0174(18) 0.020(2) 0.022(2) -0.0015(18) 0.0038(18) -0.0019(16) C25 0.020(2) 0.020(2) 0.031(3) -0.007(2) 0.007(2) -0.0039(17) C24 0.020(2) 0.030(3) 0.024(2) -0.005(2) 0.0001(19) -0.0051(18) C23 0.018(2) 0.026(3) 0.026(3) -0.004(2) -0.001(2) -0.0003(17) C32 0.0187(19) 0.019(2) 0.022(2) -0.0059(18) 0.0042(18) -0.0034(16) C36 0.023(2) 0.016(2) 0.022(2) 0.0042(18) 0.0027(19) 0.0029(17) C35 0.030(2) 0.019(2) 0.026(3) 0.004(2) 0.004(2) -0.0004(18) C34 0.039(3) 0.013(2) 0.033(3) 0.002(2) 0.010(2) -0.0023(19) C33 0.028(2) 0.020(2) 0.027(3) -0.005(2) 0.004(2) -0.0079(18) C46 0.024(2) 0.021(2) 0.022(2) 0.0029(19) 0.0036(19) 0.0016(18) C43 0.023(2) 0.034(3) 0.025(3) 0.001(2) 0.000(2) 0.004(2) C51 0.028(3) 0.060(4) 0.037(3) 0.020(3) -0.005(2) -0.001(3) C58 0.039(3) 0.047(3) 0.033(3) 0.017(3) -0.002(3) 0.005(3) C57 0.041(3) 0.098(6) 0.092(6) 0.066(5) 0.025(4) 0.037(4) C52 0.062(5) 0.110(7) 0.041(4) 0.029(5) -0.020(4) -0.048(5) C53 0.039(3) 0.100(6) 0.036(4) 0.025(4) -0.017(3) -0.032(4) C54 0.020(2) 0.042(3) 0.036(3) -0.009(3) -0.001(2) -0.005(2) C55 0.034(3) 0.037(3) 0.042(3) 0.008(3) -0.006(3) -0.010(2) C56 0.042(4) 0.099(7) 0.120(8) -0.088(6) 0.024(4) -0.029(4) C44 0.020(2) 0.028(2) 0.024(3) -0.006(2) 0.005(2) -0.0019(19) C15 0.019(2) 0.025(2) 0.026(3) 0.000(2) -0.0007(19) 0.0001(18) C14 0.023(2) 0.027(3) 0.031(3) 0.010(2) 0.003(2) 0.0025(18) C13 0.028(2) 0.016(2) 0.030(3) -0.002(2) 0.006(2) 0.0003(17) C12 0.023(2) 0.017(2) 0.025(2) -0.0049(19) 0.0048(19) 0.0002(17) N61 0.063(2) 0.157(4) 0.067(3) 0.009(3) 0.0179(19) 0.027(3) C62 0.063(2) 0.157(4) 0.067(3) 0.009(3) 0.0179(19) 0.027(3) C63 0.063(2) 0.157(4) 0.067(3) 0.009(3) 0.0179(19) 0.027(3) C72 0.063(2) 0.157(4) 0.067(3) 0.009(3) 0.0179(19) 0.027(3) N71 0.063(2) 0.157(4) 0.067(3) 0.009(3) 0.0179(19) 0.027(3) C73 0.063(2) 0.157(4) 0.067(3) 0.009(3) 0.0179(19) 0.027(3) Eu1 0.01736(16) 0.01037(17) 0.01796(17) 0.00033(9) -0.00049(11) -0.00205(8) _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 O4 N2 1.271(5) . ? O4 Eu1 2.506(3) . ? O5 N2 1.271(5) . ? O5 Eu1 2.525(3) . ? O6 N2 1.217(5) . ? O8 N3 1.260(5) . ? O8 Eu1 2.541(4) . ? O9 N3 1.223(6) . ? O7 N3 1.287(5) . ? O7 Eu1 2.488(3) . ? O2 N1 1.273(5) . ? O2 Eu1 2.504(3) . ? O3 N1 1.212(6) . ? O1 N1 1.266(6) . ? O1 Eu1 2.481(3) . ? N11 C16 1.361(6) . ? N11 C12 1.339(6) . ? N11 Eu1 2.524(4) . ? N21 C22 1.349(6) . ? N21 C26 1.342(6) . ? N21 Eu1 2.523(4) . ? N31 C32 1.360(6) . ? N31 C36 1.358(6) . ? N31 Eu1 2.564(4) . ? N45 C46 1.341(6) . ? N45 C43 1.313(6) . ? N42 N41 1.343(6) . ? N42 C44 1.330(7) . ? N41 C46 1.331(6) . ? N41 Eu1 2.529(4) . ? C16 C22 1.480(6) . ? C16 C15 1.387(6) . ? C22 C23 1.406(7) . ? C26 C25 1.400(6) . ? C26 C32 1.486(6) . ? C25 H25 0.9500 . ? C25 C24 1.383(7) . ? C24 H56 0.9500 . ? C24 C23 1.382(7) . ? C23 H23 0.9500 . ? C32 C33 1.391(6) . ? C36 C35 1.384(6) . ? C36 C46 1.478(7) . ? C35 H35 0.9500 . ? C35 C34 1.381(7) . ? C34 H34 0.9500 . ? C34 C33 1.379(7) . ? C33 H33 0.9500 . ? C43 C51 1.515(7) . ? C43 C44 1.432(7) . ? C51 C58 1.537(8) . ? C51 C57 1.524(9) . ? C51 C52 1.526(10) . ? C58 H58A 0.9800 . ? C58 H58B 0.9800 . ? C58 H58C 0.9800 . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? C52 H52A 0.9900 . ? C52 H52B 0.9900 . ? C52 C53 1.511(9) . ? C53 H53A 0.9900 . ? C53 H53B 0.9900 . ? C53 C54 1.561(9) . ? C54 C55 1.503(8) . ? C54 C56 1.534(8) . ? C54 C44 1.515(7) . ? C55 H55A 0.9800 . ? C55 H55B 0.9800 . ? C55 H55C 0.9800 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C15 H15 0.9500 . ? C15 C14 1.378(7) . ? C14 H14 0.9500 . ? C14 C13 1.389(7) . ? C13 H13 0.9500 . ? C13 C12 1.383(7) . ? C12 H12 0.9500 . ? N61 C62 1.178(11) . ? C62 C63 1.498(13) . ? C63 H63A 0.9800 . ? C63 H63B 0.9800 . ? C63 H63C 0.9800 . ? C72 N71 1.251(16) . ? C72 C73 1.391(15) . ? C73 H73A 0.9800 . ? C73 H73B 0.9800 . ? C73 H73C 0.9800 . ? 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 N2 O4 Eu1 97.1(3) . . ? N2 O5 Eu1 96.2(3) . . ? N3 O8 Eu1 95.8(3) . . ? N3 O7 Eu1 97.6(3) . . ? N1 O2 Eu1 95.6(3) . . ? N1 O1 Eu1 96.9(3) . . ? O4 N2 O5 115.6(4) . . ? O6 N2 O4 122.3(5) . . ? O6 N2 O5 122.2(5) . . ? C16 N11 Eu1 118.5(3) . . ? C12 N11 C16 118.1(4) . . ? C12 N11 Eu1 121.3(3) . . ? C22 N21 Eu1 117.9(3) . . ? C26 N21 C22 119.4(4) . . ? C26 N21 Eu1 120.5(3) . . ? C32 N31 Eu1 120.8(3) . . ? C36 N31 C32 116.7(4) . . ? C36 N31 Eu1 122.4(3) . . ? C43 N45 C46 117.2(4) . . ? C44 N42 N41 118.3(4) . . ? N42 N41 Eu1 117.0(3) . . ? C46 N41 N42 119.8(4) . . ? C46 N41 Eu1 123.3(3) . . ? O8 N3 O7 115.8(4) . . ? O9 N3 O8 123.6(4) . . ? O9 N3 O7 120.7(4) . . ? O9 N3 Eu1 177.3(3) . . ? O3 N1 O2 122.2(4) . . ? O3 N1 O1 121.6(4) . . ? O1 N1 O2 116.2(4) . . ? N11 C16 C22 115.5(4) . . ? N11 C16 C15 121.7(4) . . ? C15 C16 C22 122.8(4) . . ? N21 C22 C16 116.8(4) . . ? N21 C22 C23 121.0(4) . . ? C23 C22 C16 122.2(4) . . ? N21 C26 C25 122.1(4) . . ? N21 C26 C32 116.8(4) . . ? C25 C26 C32 121.1(4) . . ? C26 C25 H25 120.7 . . ? C24 C25 C26 118.7(4) . . ? C24 C25 H25 120.7 . . ? C25 C24 H56 120.3 . . ? C23 C24 C25 119.4(5) . . ? C23 C24 H56 120.3 . . ? C22 C23 H23 120.3 . . ? C24 C23 C22 119.4(5) . . ? C24 C23 H23 120.3 . . ? N31 C32 C26 114.9(4) . . ? N31 C32 C33 122.2(4) . . ? C33 C32 C26 122.9(4) . . ? N31 C36 C35 124.2(4) . . ? N31 C36 C46 114.5(4) . . ? C35 C36 C46 121.2(4) . . ? C36 C35 H35 121.2 . . ? C34 C35 C36 117.5(5) . . ? C34 C35 H35 121.2 . . ? C35 C34 H34 120.0 . . ? C33 C34 C35 120.1(4) . . ? C33 C34 H34 120.0 . . ? C32 C33 H33 120.4 . . ? C34 C33 C32 119.2(4) . . ? C34 C33 H33 120.4 . . ? N45 C46 C36 118.6(4) . . ? N41 C46 N45 124.4(5) . . ? N41 C46 C36 117.0(4) . . ? N45 C43 C51 117.5(5) . . ? N45 C43 C44 119.6(5) . . ? C44 C43 C51 123.0(5) . . ? C43 C51 C58 110.2(4) . . ? C43 C51 C57 105.8(5) . . ? C43 C51 C52 109.5(6) . . ? C57 C51 C58 108.6(6) . . ? C57 C51 C52 112.9(6) . . ? C52 C51 C58 109.8(6) . . ? C51 C58 H58A 109.5 . . ? C51 C58 H58B 109.5 . . ? C51 C58 H58C 109.5 . . ? H58A C58 H58B 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C51 C57 H57A 109.5 . . ? C51 C57 H57B 109.5 . . ? C51 C57 H57C 109.5 . . ? H57A C57 H57B 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? C51 C52 H52A 109.1 . . ? C51 C52 H52B 109.1 . . ? H52A C52 H52B 107.8 . . ? C53 C52 C51 112.5(7) . . ? C53 C52 H52A 109.1 . . ? C53 C52 H52B 109.1 . . ? C52 C53 H53A 108.9 . . ? C52 C53 H53B 108.9 . . ? C52 C53 C54 113.2(5) . . ? H53A C53 H53B 107.8 . . ? C54 C53 H53A 108.9 . . ? C54 C53 H53B 108.9 . . ? C55 C54 C53 109.3(5) . . ? C55 C54 C56 109.2(6) . . ? C55 C54 C44 111.4(5) . . ? C56 C54 C53 110.9(7) . . ? C44 C54 C53 109.0(5) . . ? C44 C54 C56 107.1(4) . . ? C54 C55 H55A 109.5 . . ? C54 C55 H55B 109.5 . . ? C54 C55 H55C 109.5 . . ? H55A C55 H55B 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? C54 C56 H56A 109.5 . . ? C54 C56 H56B 109.5 . . ? C54 C56 H56C 109.5 . . ? H56A C56 H56B 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? N42 C44 C43 120.6(5) . . ? N42 C44 C54 115.3(5) . . ? C43 C44 C54 124.2(5) . . ? C16 C15 H15 120.3 . . ? C14 C15 C16 119.4(5) . . ? C14 C15 H15 120.3 . . ? C15 C14 H14 120.4 . . ? C15 C14 C13 119.3(4) . . ? C13 C14 H14 120.4 . . ? C14 C13 H13 120.8 . . ? C12 C13 C14 118.3(4) . . ? C12 C13 H13 120.8 . . ? N11 C12 C13 123.2(4) . . ? N11 C12 H12 118.4 . . ? C13 C12 H12 118.4 . . ? N61 C62 C63 176.5(15) . . ? C62 C63 H63A 109.5 . . ? C62 C63 H63B 109.5 . . ? C62 C63 H63C 109.5 . . ? H63A C63 H63B 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? N71 C72 C73 172.7(12) . . ? C72 C73 H73A 109.5 . . ? C72 C73 H73B 109.5 . . ? C72 C73 H73C 109.5 . . ? H73A C73 H73B 109.5 . . ? H73A C73 H73C 109.5 . . ? H73B C73 H73C 109.5 . . ? O4 Eu1 O5 50.62(11) . . ? O4 Eu1 O8 106.91(11) . . ? O4 Eu1 N11 80.19(11) . . ? O4 Eu1 N21 139.59(12) . . ? O4 Eu1 N31 155.91(11) . . ? O4 Eu1 N41 94.74(12) . . ? O5 Eu1 O8 67.28(11) . . ? O5 Eu1 N31 109.61(11) . . ? O5 Eu1 N41 69.63(12) . . ? O8 Eu1 N31 70.11(11) . . ? O7 Eu1 O4 74.04(11) . . ? O7 Eu1 O5 71.35(11) . . ? O7 Eu1 O8 50.77(10) . . ? O7 Eu1 O2 130.85(10) . . ? O7 Eu1 N11 68.18(11) . . ? O7 Eu1 N21 75.65(11) . . ? O7 Eu1 N31 115.89(11) . . ? O7 Eu1 N41 136.73(12) . . ? O2 Eu1 O4 66.44(11) . . ? O2 Eu1 O5 102.29(11) . . ? O2 Eu1 O8 169.00(12) . . ? O2 Eu1 N11 77.14(12) . . ? O2 Eu1 N21 118.74(12) . . ? O2 Eu1 N31 112.08(12) . . ? O2 Eu1 N41 76.00(12) . . ? O1 Eu1 O4 117.37(12) . . ? O1 Eu1 O5 142.39(12) . . ? O1 Eu1 O8 135.57(11) . . ? O1 Eu1 O7 145.20(11) . . ? O1 Eu1 O2 51.22(11) . . ? O1 Eu1 N11 81.06(12) . . ? O1 Eu1 N21 76.48(12) . . ? O1 Eu1 N31 68.07(12) . . ? O1 Eu1 N41 77.29(13) . . ? N11 Eu1 O5 122.86(12) . . ? N11 Eu1 O8 111.07(12) . . ? N11 Eu1 N31 123.62(12) . . ? N11 Eu1 N41 152.40(13) . . ? N21 Eu1 O5 138.18(12) . . ? N21 Eu1 O8 72.11(12) . . ? N21 Eu1 N11 63.97(12) . . ? N21 Eu1 N31 63.59(12) . . ? N21 Eu1 N41 125.68(12) . . ? N41 Eu1 O8 96.41(13) . . ? N41 Eu1 N31 62.64(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 O4 Eu1 O5 3.9(3) . . . . ? N2 O4 Eu1 O8 43.4(3) . . . . ? N2 O4 Eu1 O7 82.6(3) . . . . ? N2 O4 Eu1 O2 -127.3(3) . . . . ? N2 O4 Eu1 O1 -132.9(3) . . . . ? N2 O4 Eu1 N11 152.6(3) . . . . ? N2 O4 Eu1 N21 125.5(3) . . . . ? N2 O4 Eu1 N31 -35.6(5) . . . . ? N2 O4 Eu1 N41 -54.8(3) . . . . ? N2 O5 Eu1 O4 -3.9(3) . . . . ? N2 O5 Eu1 O8 -142.6(3) . . . . ? N2 O5 Eu1 O7 -88.3(3) . . . . ? N2 O5 Eu1 O2 41.0(3) . . . . ? N2 O5 Eu1 O1 80.9(3) . . . . ? N2 O5 Eu1 N11 -41.5(3) . . . . ? N2 O5 Eu1 N21 -128.0(3) . . . . ? N2 O5 Eu1 N31 160.1(3) . . . . ? N2 O5 Eu1 N41 110.8(3) . . . . ? N11 C16 C22 N21 -2.0(6) . . . . ? N11 C16 C22 C23 179.3(4) . . . . ? N11 C16 C15 C14 1.4(7) . . . . ? N21 C22 C23 C24 -2.6(7) . . . . ? N21 C26 C25 C24 0.7(7) . . . . ? N21 C26 C32 N31 14.3(6) . . . . ? N21 C26 C32 C33 -163.2(4) . . . . ? N31 C32 C33 C34 1.8(7) . . . . ? N31 C36 C35 C34 1.1(7) . . . . ? N31 C36 C46 N45 -178.1(4) . . . . ? N31 C36 C46 N41 2.1(6) . . . . ? N45 C43 C51 C58 44.1(7) . . . . ? N45 C43 C51 C57 -73.1(6) . . . . ? N45 C43 C51 C52 164.9(5) . . . . ? N45 C43 C44 N42 -5.4(7) . . . . ? N45 C43 C44 C54 176.0(5) . . . . ? N42 N41 C46 N45 -3.5(7) . . . . ? N42 N41 C46 C36 176.4(4) . . . . ? N42 N41 Eu1 O4 -6.0(3) . . . . ? N42 N41 Eu1 O5 -50.7(3) . . . . ? N42 N41 Eu1 O8 -113.6(3) . . . . ? N42 N41 Eu1 O7 -77.6(4) . . . . ? N42 N41 Eu1 O2 58.3(3) . . . . ? N42 N41 Eu1 O1 111.1(3) . . . . ? N42 N41 Eu1 N11 71.9(4) . . . . ? N42 N41 Eu1 N21 173.9(3) . . . . ? N42 N41 Eu1 N31 -177.3(4) . . . . ? N41 N42 C44 C43 3.1(7) . . . . ? N41 N42 C44 C54 -178.2(4) . . . . ? N3 O8 Eu1 O4 51.3(3) . . . . ? N3 O8 Eu1 O5 83.5(3) . . . . ? N3 O8 Eu1 O7 -0.4(2) . . . . ? N3 O8 Eu1 O2 102.6(6) . . . . ? N3 O8 Eu1 O1 -133.4(3) . . . . ? N3 O8 Eu1 N11 -34.4(3) . . . . ? N3 O8 Eu1 N21 -86.2(3) . . . . ? N3 O8 Eu1 N31 -153.9(3) . . . . ? N3 O8 Eu1 N41 148.3(3) . . . . ? N3 O7 Eu1 O4 -128.2(3) . . . . ? N3 O7 Eu1 O5 -75.1(2) . . . . ? N3 O7 Eu1 O8 0.4(2) . . . . ? N3 O7 Eu1 O2 -165.4(2) . . . . ? N3 O7 Eu1 O1 116.5(3) . . . . ? N3 O7 Eu1 N11 146.2(3) . . . . ? N3 O7 Eu1 N21 78.8(2) . . . . ? N3 O7 Eu1 N31 28.2(3) . . . . ? N3 O7 Eu1 N41 -48.5(3) . . . . ? N1 O2 Eu1 O4 -173.4(3) . . . . ? N1 O2 Eu1 O5 150.0(3) . . . . ? N1 O2 Eu1 O8 132.0(5) . . . . ? N1 O2 Eu1 O7 -134.1(3) . . . . ? N1 O2 Eu1 O1 0.1(3) . . . . ? N1 O2 Eu1 N11 -88.7(3) . . . . ? N1 O2 Eu1 N21 -38.4(3) . . . . ? N1 O2 Eu1 N31 32.7(3) . . . . ? N1 O2 Eu1 N41 84.9(3) . . . . ? N1 O1 Eu1 O4 6.5(3) . . . . ? N1 O1 Eu1 O5 -53.6(4) . . . . ? N1 O1 Eu1 O8 -168.4(3) . . . . ? N1 O1 Eu1 O7 108.2(3) . . . . ? N1 O1 Eu1 O2 -0.1(3) . . . . ? N1 O1 Eu1 N11 80.5(3) . . . . ? N1 O1 Eu1 N21 145.7(3) . . . . ? N1 O1 Eu1 N31 -147.6(3) . . . . ? N1 O1 Eu1 N41 -82.3(3) . . . . ? C16 N11 C12 C13 0.9(7) . . . . ? C16 N11 Eu1 O4 -138.9(3) . . . . ? C16 N11 Eu1 O5 -110.3(3) . . . . ? C16 N11 Eu1 O8 -34.4(3) . . . . ? C16 N11 Eu1 O7 -62.2(3) . . . . ? C16 N11 Eu1 O2 153.3(3) . . . . ? C16 N11 Eu1 O1 101.2(3) . . . . ? C16 N11 Eu1 N2 -127.2(3) . . . . ? C16 N11 Eu1 N21 21.9(3) . . . . ? C16 N11 Eu1 N31 45.1(4) . . . . ? C16 N11 Eu1 N41 139.8(3) . . . . ? C16 C22 C23 C24 176.1(4) . . . . ? C16 C15 C14 C13 0.1(7) . . . . ? C22 N21 C26 C25 -3.6(6) . . . . ? C22 N21 C26 C32 175.0(4) . . . . ? C22 N21 Eu1 O4 7.2(4) . . . . ? C22 N21 Eu1 O5 88.2(3) . . . . ? C22 N21 Eu1 O8 102.5(3) . . . . ? C22 N21 Eu1 O7 49.6(3) . . . . ? C22 N21 Eu1 O2 -79.5(3) . . . . ? C22 N21 Eu1 O1 -109.4(3) . . . . ? C22 N21 Eu1 N11 -22.8(3) . . . . ? C22 N21 Eu1 N31 178.6(4) . . . . ? C22 N21 Eu1 N41 -172.6(3) . . . . ? C22 C16 C15 C14 -177.1(4) . . . . ? C26 N21 C22 C16 -174.2(4) . . . . ? C26 N21 C22 C23 4.5(6) . . . . ? C26 N21 Eu1 O4 -155.8(3) . . . . ? C26 N21 Eu1 O5 -74.8(4) . . . . ? C26 N21 Eu1 O8 -60.5(3) . . . . ? C26 N21 Eu1 O7 -113.4(3) . . . . ? C26 N21 Eu1 O2 117.5(3) . . . . ? C26 N21 Eu1 O1 87.6(3) . . . . ? C26 N21 Eu1 N11 174.1(4) . . . . ? C26 N21 Eu1 N31 15.6(3) . . . . ? C26 N21 Eu1 N41 24.4(4) . . . . ? C26 C25 C24 C23 1.3(7) . . . . ? C26 C32 C33 C34 179.1(4) . . . . ? C25 C26 C32 N31 -167.2(4) . . . . ? C25 C26 C32 C33 15.4(7) . . . . ? C25 C24 C23 C22 -0.3(7) . . . . ? C32 N31 C36 C35 -1.6(7) . . . . ? C32 N31 C36 C46 178.3(4) . . . . ? C32 N31 Eu1 O4 159.0(3) . . . . ? C32 N31 Eu1 O5 127.5(3) . . . . ? C32 N31 Eu1 O8 71.9(3) . . . . ? C32 N31 Eu1 O7 49.3(3) . . . . ? C32 N31 Eu1 O2 -119.7(3) . . . . ? C32 N31 Eu1 O1 -92.8(3) . . . . ? C32 N31 Eu1 N11 -30.7(4) . . . . ? C32 N31 Eu1 N21 -7.4(3) . . . . ? C32 N31 Eu1 N41 -179.4(4) . . . . ? C32 C26 C25 C24 -177.8(4) . . . . ? C36 N31 C32 C26 -177.4(4) . . . . ? C36 N31 C32 C33 0.1(6) . . . . ? C36 N31 Eu1 O4 -23.8(5) . . . . ? C36 N31 Eu1 O5 -55.3(4) . . . . ? C36 N31 Eu1 O8 -110.9(3) . . . . ? C36 N31 Eu1 O7 -133.5(3) . . . . ? C36 N31 Eu1 O2 57.6(4) . . . . ? C36 N31 Eu1 O1 84.4(3) . . . . ? C36 N31 Eu1 N11 146.5(3) . . . . ? C36 N31 Eu1 N21 169.8(4) . . . . ? C36 N31 Eu1 N41 -2.2(3) . . . . ? C36 C35 C34 C33 0.9(7) . . . . ? C35 C36 C46 N45 1.9(7) . . . . ? C35 C36 C46 N41 -178.0(4) . . . . ? C35 C34 C33 C32 -2.3(7) . . . . ? C46 N45 C43 C51 -176.4(4) . . . . ? C46 N45 C43 C44 3.2(7) . . . . ? C46 N41 Eu1 O4 174.8(4) . . . . ? C46 N41 Eu1 O5 130.0(4) . . . . ? C46 N41 Eu1 O8 67.1(4) . . . . ? C46 N41 Eu1 O7 103.1(4) . . . . ? C46 N41 Eu1 O2 -121.0(4) . . . . ? C46 N41 Eu1 O1 -68.2(4) . . . . ? C46 N41 Eu1 N11 -107.4(4) . . . . ? C46 N41 Eu1 N21 -5.4(5) . . . . ? C46 N41 Eu1 N31 3.5(3) . . . . ? C46 C36 C35 C34 -178.8(4) . . . . ? C43 N45 C46 N41 1.1(7) . . . . ? C43 N45 C46 C36 -178.7(4) . . . . ? C43 C51 C52 C53 47.7(9) . . . . ? C51 C43 C44 N42 174.1(5) . . . . ? C51 C43 C44 C54 -4.4(8) . . . . ? C51 C52 C53 C54 -64.7(11) . . . . ? C58 C51 C52 C53 168.8(7) . . . . ? C57 C51 C52 C53 -69.9(9) . . . . ? C52 C53 C54 C55 163.8(7) . . . . ? C52 C53 C54 C56 -75.9(9) . . . . ? C52 C53 C54 C44 41.8(9) . . . . ? C53 C54 C44 N42 172.6(5) . . . . ? C53 C54 C44 C43 -8.8(7) . . . . ? C55 C54 C44 N42 52.0(6) . . . . ? C55 C54 C44 C43 -129.4(5) . . . . ? C56 C54 C44 N42 -67.4(7) . . . . ? C56 C54 C44 C43 111.3(7) . . . . ? C44 N42 N41 C46 1.1(7) . . . . ? C44 N42 N41 Eu1 -178.2(3) . . . . ? C44 C43 C51 C58 -135.5(5) . . . . ? C44 C43 C51 C57 107.3(6) . . . . ? C44 C43 C51 C52 -14.7(7) . . . . ? C15 C16 C22 N21 176.6(4) . . . . ? C15 C16 C22 C23 -2.2(7) . . . . ? C15 C14 C13 C12 -1.1(7) . . . . ? C14 C13 C12 N11 0.6(7) . . . . ? C12 N11 C16 C22 176.7(4) . . . . ? C12 N11 C16 C15 -1.9(6) . . . . ? C12 N11 Eu1 O4 24.2(3) . . . . ? C12 N11 Eu1 O5 52.8(4) . . . . ? C12 N11 Eu1 O8 128.7(3) . . . . ? C12 N11 Eu1 O7 100.9(4) . . . . ? C12 N11 Eu1 O2 -43.6(3) . . . . ? C12 N11 Eu1 O1 -95.7(4) . . . . ? C12 N11 Eu1 N21 -175.0(4) . . . . ? C12 N11 Eu1 N31 -151.8(3) . . . . ? C12 N11 Eu1 N41 -57.1(5) . . . . ? Eu1 O4 N2 O5 -6.7(4) . . . . ? Eu1 O4 N2 O6 172.8(4) . . . . ? Eu1 O5 N2 O4 6.6(4) . . . . ? Eu1 O5 N2 O6 -172.9(4) . . . . ? Eu1 O8 N3 O9 -178.9(4) . . . . ? Eu1 O8 N3 O7 0.7(4) . . . . ? Eu1 O7 N3 O8 -0.7(4) . . . . ? Eu1 O7 N3 O9 178.9(4) . . . . ? Eu1 O2 N1 O3 179.9(4) . . . . ? Eu1 O2 N1 O1 -0.2(4) . . . . ? Eu1 O1 N1 O2 0.2(4) . . . . ? Eu1 O1 N1 O3 -179.9(4) . . . . ? Eu1 N11 C16 C22 -19.7(5) . . . . ? Eu1 N11 C16 C15 161.8(3) . . . . ? Eu1 N11 C12 C13 -162.3(3) . . . . ? Eu1 N21 C22 C16 22.6(5) . . . . ? Eu1 N21 C22 C23 -158.7(3) . . . . ? Eu1 N21 C26 C25 159.2(3) . . . . ? Eu1 N21 C26 C32 -22.3(5) . . . . ? Eu1 N31 C32 C26 -0.1(5) . . . . ? Eu1 N31 C32 C33 177.4(3) . . . . ? Eu1 N31 C36 C35 -178.9(4) . . . . ? Eu1 N31 C36 C46 1.0(5) . . . . ? Eu1 N41 C46 N45 175.8(3) . . . . ? Eu1 N41 C46 C36 -4.4(6) . . . . ? data_1 _database_code_depnum_ccdc_archive 'CCDC 869235' #TrackingRef '- CIF Files.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H26 N6 ' _chemical_formula_weight 422.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 8.5515(11) _cell_length_b 8.5740(11) _cell_length_c 16.214(2) _cell_angle_alpha 81.677(11) _cell_angle_beta 85.060(11) _cell_angle_gamma 66.015(12) _cell_volume 1074.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7578 _cell_measurement_theta_min 2.54 _cell_measurement_theta_max 30.00 _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_standards_number n/a _diffrn_measurement_device 'Oxford Diffaction X-Calibur System' _diffrn_measurement_method '321 frames, counting time 10 s.' _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% n/a _diffrn_reflns_number 7578 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.1394 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5965 _reflns_number_gt 2754 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Crysalis, Oxford Diffraction' _computing_cell_refinement 'Crysalis, Oxford Diffraction' _computing_data_reduction 'Crysalis, Oxford Diffraction' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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 ; _refine_ls_weighting_details w=1/[\s^2^(Fo^2^)+(0.0458P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5965 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1300 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 0.802 _refine_ls_restrained_S_all 0.802 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 0.40102(19) 0.69556(18) 0.23451(9) 0.0262(4) Uani 1 1 d . . . C12 C 0.2670(2) 0.7435(2) 0.18571(12) 0.0294(5) Uani 1 1 d . . . H12 H 0.2623 0.8191 0.1378 0.035 Uiso 1 1 calc R . . C13 C 0.1360(2) 0.6889(2) 0.20142(12) 0.0266(5) Uani 1 1 d . . . H13 H 0.0454 0.7273 0.1654 0.032 Uiso 1 1 calc R . . C14 C 0.1421(2) 0.5760(2) 0.27168(11) 0.0253(4) Uani 1 1 d . . . H14 H 0.0552 0.5367 0.2846 0.030 Uiso 1 1 calc R . . C15 C 0.2798(2) 0.5223(2) 0.32263(11) 0.0228(4) Uani 1 1 d . . . H15 H 0.2880 0.4444 0.3701 0.027 Uiso 1 1 calc R . . C16 C 0.4064(2) 0.5852(2) 0.30278(11) 0.0201(4) Uani 1 1 d . . . N21 N 0.59608(18) 0.38842(17) 0.40782(9) 0.0195(3) Uani 1 1 d . . . C22 C 0.5544(2) 0.5374(2) 0.35731(10) 0.0193(4) Uani 1 1 d . . . C23 C 0.6391(2) 0.6457(2) 0.35700(11) 0.0219(4) Uani 1 1 d . . . H23 H 0.6061 0.7484 0.3215 0.026 Uiso 1 1 calc R . . C24 C 0.7725(2) 0.5991(2) 0.40978(11) 0.0219(4) Uani 1 1 d . . . H24 H 0.8311 0.6696 0.4105 0.026 Uiso 1 1 calc R . . C25 C 0.8179(2) 0.4459(2) 0.46164(11) 0.0206(4) Uani 1 1 d . . . H25 H 0.9080 0.4110 0.4977 0.025 Uiso 1 1 calc R . . C26 C 0.7265(2) 0.3443(2) 0.45910(11) 0.0184(4) Uani 1 1 d . . . N31 N 0.88526(18) 0.14517(16) 0.57222(9) 0.0186(3) Uani 1 1 d . . . C32 C 0.7687(2) 0.1795(2) 0.51471(11) 0.0191(4) Uani 1 1 d . . . C36 C 0.9215(2) 0.0007(2) 0.62523(10) 0.0180(4) Uani 1 1 d . . . C33 C 0.6899(2) 0.0694(2) 0.50653(11) 0.0211(4) Uani 1 1 d . . . H33 H 0.6120 0.0958 0.4647 0.025 Uiso 1 1 calc R . . C34 C 0.7283(2) -0.0790(2) 0.56101(11) 0.0239(4) Uani 1 1 d . . . H34 H 0.6771 -0.1545 0.5566 0.029 Uiso 1 1 calc R . . C35 C 0.8443(2) -0.1137(2) 0.62223(11) 0.0216(4) Uani 1 1 d . . . H35 H 0.8705 -0.2116 0.6608 0.026 Uiso 1 1 calc R . . N45 N 1.05098(18) -0.15060(17) 0.75513(9) 0.0190(3) Uani 1 1 d . . . C46 C 1.0503(2) -0.0362(2) 0.68907(10) 0.0178(4) Uani 1 1 d . . . N41 N 1.15683(19) 0.04474(18) 0.67597(9) 0.0226(4) Uani 1 1 d . . . N42 N 1.26969(19) 0.01453(18) 0.73493(9) 0.0218(4) Uani 1 1 d . . . C43 C 1.2734(2) -0.0931(2) 0.80348(11) 0.0185(4) Uani 1 1 d . . . C44 C 1.1638(2) -0.1807(2) 0.81292(10) 0.0171(4) Uani 1 1 d . . . C51 C 1.1625(2) -0.3063(2) 0.88871(11) 0.0203(4) Uani 1 1 d . . . C511 C 1.1498(3) -0.4653(2) 0.86177(12) 0.0286(5) Uani 1 1 d . . . H51A H 1.0436 -0.4314 0.8345 0.043 Uiso 1 1 calc R . . H51B H 1.1544 -0.5464 0.9100 0.043 Uiso 1 1 calc R . . H51C H 1.2435 -0.5176 0.8240 0.043 Uiso 1 1 calc R . . C512 C 1.0030(2) -0.2166(2) 0.94278(12) 0.0283(5) Uani 1 1 d . . . H51D H 1.0074 -0.1153 0.9592 0.042 Uiso 1 1 calc R . . H51E H 0.9998 -0.2934 0.9916 0.042 Uiso 1 1 calc R . . H51F H 0.9022 -0.1849 0.9114 0.042 Uiso 1 1 calc R . . C52 C 1.3254(2) -0.3611(2) 0.93731(12) 0.0266(5) Uani 1 1 d . . . H52A H 1.3116 -0.4197 0.9915 0.032 Uiso 1 1 calc R . . H52B H 1.4204 -0.4419 0.9078 0.032 Uiso 1 1 calc R . . C53 C 1.3674(2) -0.2105(2) 0.94925(11) 0.0246(4) Uani 1 1 d . . . H53A H 1.4665 -0.2518 0.9840 0.030 Uiso 1 1 calc R . . H53B H 1.2719 -0.1295 0.9785 0.030 Uiso 1 1 calc R . . C54 C 1.4046(2) -0.1167(2) 0.86669(11) 0.0208(4) Uani 1 1 d . . . C541 C 1.5825(2) -0.2210(3) 0.83154(13) 0.0378(5) Uani 1 1 d . . . H54D H 1.5867 -0.3286 0.8188 0.057 Uiso 1 1 calc R . . H54E H 1.6665 -0.2422 0.8720 0.057 Uiso 1 1 calc R . . H54F H 1.6060 -0.1579 0.7817 0.057 Uiso 1 1 calc R . . C542 C 1.3962(3) 0.0579(2) 0.88326(12) 0.0308(5) Uani 1 1 d . . . H54A H 1.4228 0.1165 0.8325 0.046 Uiso 1 1 calc R . . H54B H 1.4774 0.0409 0.9246 0.046 Uiso 1 1 calc R . . H54C H 1.2830 0.1258 0.9031 0.046 Uiso 1 1 calc 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 N11 0.0251(9) 0.0282(9) 0.0215(9) 0.0054(7) -0.0053(7) -0.0086(7) C12 0.0308(12) 0.0286(11) 0.0224(11) 0.0077(8) -0.0079(9) -0.0075(9) C13 0.0231(11) 0.0265(10) 0.0253(11) -0.0031(8) -0.0079(9) -0.0036(8) C14 0.0235(11) 0.0253(10) 0.0285(11) -0.0048(8) -0.0025(9) -0.0103(8) C15 0.0289(11) 0.0182(9) 0.0186(10) 0.0005(7) -0.0024(9) -0.0073(8) C16 0.0225(10) 0.0173(9) 0.0173(10) -0.0013(7) -0.0004(8) -0.0050(8) N21 0.0208(8) 0.0179(8) 0.0170(8) 0.0005(6) -0.0004(7) -0.0060(6) C22 0.0198(10) 0.0196(9) 0.0156(9) -0.0015(7) -0.0010(8) -0.0049(7) C23 0.0264(11) 0.0195(9) 0.0195(10) 0.0034(7) -0.0020(8) -0.0106(8) C24 0.0249(10) 0.0202(9) 0.0235(10) -0.0003(8) -0.0010(9) -0.0127(8) C25 0.0209(10) 0.0222(9) 0.0178(10) -0.0008(7) -0.0034(8) -0.0076(8) C26 0.0204(10) 0.0149(9) 0.0170(9) -0.0017(7) 0.0013(8) -0.0044(7) N31 0.0195(8) 0.0165(7) 0.0187(8) -0.0008(6) -0.0018(7) -0.0062(6) C32 0.0176(9) 0.0173(9) 0.0194(10) -0.0008(7) -0.0006(8) -0.0044(7) C36 0.0182(9) 0.0181(9) 0.0158(9) -0.0011(7) -0.0005(8) -0.0056(7) C33 0.0190(10) 0.0234(10) 0.0196(10) 0.0022(8) -0.0044(8) -0.0079(8) C34 0.0239(10) 0.0217(10) 0.0294(11) 0.0017(8) -0.0062(9) -0.0129(8) C35 0.0233(10) 0.0191(9) 0.0211(10) 0.0033(7) -0.0028(8) -0.0087(7) N45 0.0230(8) 0.0167(7) 0.0175(8) -0.0007(6) -0.0016(7) -0.0085(6) C46 0.0176(10) 0.0161(9) 0.0183(10) -0.0026(7) 0.0007(8) -0.0053(7) N41 0.0249(9) 0.0240(8) 0.0201(8) 0.0016(6) -0.0036(7) -0.0117(7) N42 0.0252(9) 0.0222(8) 0.0207(8) 0.0007(6) -0.0048(7) -0.0124(7) C43 0.0188(10) 0.0138(8) 0.0205(10) -0.0024(7) 0.0002(8) -0.0041(7) C44 0.0193(10) 0.0127(8) 0.0184(9) -0.0023(7) -0.0011(8) -0.0051(7) C51 0.0233(10) 0.0184(9) 0.0192(10) 0.0021(7) -0.0050(8) -0.0089(7) C511 0.0409(12) 0.0223(10) 0.0248(11) 0.0021(8) -0.0043(10) -0.0159(9) C512 0.0294(11) 0.0294(11) 0.0250(11) 0.0021(8) 0.0012(9) -0.0128(9) C52 0.0289(11) 0.0219(10) 0.0277(11) 0.0085(8) -0.0105(9) -0.0106(8) C53 0.0281(11) 0.0207(9) 0.0244(11) 0.0027(8) -0.0097(9) -0.0090(8) C54 0.0228(10) 0.0200(9) 0.0213(10) 0.0014(8) -0.0054(8) -0.0106(8) C541 0.0227(11) 0.0525(14) 0.0387(13) -0.0130(11) -0.0005(10) -0.0131(10) C542 0.0474(13) 0.0295(11) 0.0243(11) 0.0009(8) -0.0078(10) -0.0245(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.337(2) . ? N11 C16 1.339(2) . ? C12 C13 1.372(3) . ? C13 C14 1.374(2) . ? C14 C15 1.378(2) . ? C15 C16 1.389(2) . ? C16 C22 1.490(2) . ? N21 C26 1.343(2) . ? N21 C22 1.344(2) . ? C22 C23 1.390(2) . ? C23 C24 1.375(2) . ? C24 C25 1.380(2) . ? C25 C26 1.393(2) . ? C26 C32 1.488(2) . ? N31 C32 1.339(2) . ? N31 C36 1.340(2) . ? C32 C33 1.390(2) . ? C36 C35 1.396(2) . ? C36 C46 1.484(2) . ? C33 C34 1.375(2) . ? C34 C35 1.378(2) . ? N45 C44 1.326(2) . ? N45 C46 1.342(2) . ? C46 N41 1.340(2) . ? N41 N42 1.3403(19) . ? N42 C43 1.332(2) . ? C43 C44 1.407(2) . ? C43 C54 1.518(2) . ? C44 C51 1.515(2) . ? C51 C52 1.527(2) . ? C51 C512 1.535(2) . ? C51 C511 1.537(2) . ? C52 C53 1.515(2) . ? C53 C54 1.538(2) . ? C54 C541 1.526(2) . ? C54 C542 1.531(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C16 116.77(17) . . ? N11 C12 C13 124.59(18) . . ? C12 C13 C14 118.32(18) . . ? C13 C14 C15 118.48(18) . . ? C14 C15 C16 119.63(17) . . ? N11 C16 C15 122.20(16) . . ? N11 C16 C22 115.74(17) . . ? C15 C16 C22 122.04(16) . . ? C26 N21 C22 117.48(15) . . ? N21 C22 C23 122.78(16) . . ? N21 C22 C16 116.26(16) . . ? C23 C22 C16 120.93(16) . . ? C24 C23 C22 119.19(16) . . ? C23 C24 C25 118.80(17) . . ? C24 C25 C26 118.92(17) . . ? N21 C26 C25 122.81(15) . . ? N21 C26 C32 116.24(16) . . ? C25 C26 C32 120.94(16) . . ? C32 N31 C36 117.62(15) . . ? N31 C32 C33 122.76(16) . . ? N31 C32 C26 116.16(16) . . ? C33 C32 C26 121.09(16) . . ? N31 C36 C35 122.83(16) . . ? N31 C36 C46 117.36(16) . . ? C35 C36 C46 119.81(15) . . ? C34 C33 C32 119.22(17) . . ? C33 C34 C35 118.76(17) . . ? C34 C35 C36 118.77(16) . . ? C44 N45 C46 116.47(15) . . ? N41 C46 N45 125.43(16) . . ? N41 C46 C36 117.95(15) . . ? N45 C46 C36 116.62(16) . . ? C46 N41 N42 117.68(14) . . ? C43 N42 N41 120.00(15) . . ? N42 C43 C44 120.27(16) . . ? N42 C43 C54 115.75(16) . . ? C44 C43 C54 123.95(15) . . ? N45 C44 C43 120.04(15) . . ? N45 C44 C51 116.81(16) . . ? C43 C44 C51 123.11(16) . . ? C44 C51 C52 110.01(15) . . ? C44 C51 C512 107.86(14) . . ? C52 C51 C512 110.83(15) . . ? C44 C51 C511 110.13(14) . . ? C52 C51 C511 109.70(14) . . ? C512 C51 C511 108.29(16) . . ? C53 C52 C51 112.63(14) . . ? C52 C53 C54 113.14(15) . . ? C43 C54 C541 108.45(15) . . ? C43 C54 C542 110.52(14) . . ? C541 C54 C542 109.25(16) . . ? C43 C54 C53 109.48(15) . . ? C541 C54 C53 110.58(15) . . ? C542 C54 C53 108.55(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C16 N11 C12 C13 0.7(3) . . . . ? N11 C12 C13 C14 -0.5(3) . . . . ? C12 C13 C14 C15 -0.4(3) . . . . ? C13 C14 C15 C16 1.1(3) . . . . ? C12 N11 C16 C15 0.1(3) . . . . ? C12 N11 C16 C22 -178.41(15) . . . . ? C14 C15 C16 N11 -1.0(3) . . . . ? C14 C15 C16 C22 177.41(15) . . . . ? C26 N21 C22 C23 -0.6(2) . . . . ? C26 N21 C22 C16 -178.43(14) . . . . ? N11 C16 C22 N21 -157.70(15) . . . . ? C15 C16 C22 N21 23.8(2) . . . . ? N11 C16 C22 C23 24.4(2) . . . . ? C15 C16 C22 C23 -154.10(17) . . . . ? N21 C22 C23 C24 0.6(3) . . . . ? C16 C22 C23 C24 178.37(16) . . . . ? C22 C23 C24 C25 -0.1(3) . . . . ? C23 C24 C25 C26 -0.4(3) . . . . ? C22 N21 C26 C25 0.0(2) . . . . ? C22 N21 C26 C32 179.52(14) . . . . ? C24 C25 C26 N21 0.4(3) . . . . ? C24 C25 C26 C32 -179.02(15) . . . . ? C36 N31 C32 C33 -2.2(2) . . . . ? C36 N31 C32 C26 177.64(14) . . . . ? N21 C26 C32 N31 -172.71(14) . . . . ? C25 C26 C32 N31 6.8(2) . . . . ? N21 C26 C32 C33 7.2(2) . . . . ? C25 C26 C32 C33 -173.34(16) . . . . ? C32 N31 C36 C35 0.5(2) . . . . ? C32 N31 C36 C46 -179.72(15) . . . . ? N31 C32 C33 C34 2.0(3) . . . . ? C26 C32 C33 C34 -177.85(16) . . . . ? C32 C33 C34 C35 0.0(3) . . . . ? C33 C34 C35 C36 -1.7(3) . . . . ? N31 C36 C35 C34 1.5(3) . . . . ? C46 C36 C35 C34 -178.34(16) . . . . ? C44 N45 C46 N41 2.2(2) . . . . ? C44 N45 C46 C36 -178.65(14) . . . . ? N31 C36 C46 N41 -19.1(2) . . . . ? C35 C36 C46 N41 160.76(16) . . . . ? N31 C36 C46 N45 161.70(14) . . . . ? C35 C36 C46 N45 -18.5(2) . . . . ? N45 C46 N41 N42 -2.6(2) . . . . ? C36 C46 N41 N42 178.19(14) . . . . ? C46 N41 N42 C43 0.2(2) . . . . ? N41 N42 C43 C44 2.5(2) . . . . ? N41 N42 C43 C54 -179.34(14) . . . . ? C46 N45 C44 C43 0.6(2) . . . . ? C46 N45 C44 C51 178.53(14) . . . . ? N42 C43 C44 N45 -2.9(2) . . . . ? C54 C43 C44 N45 179.04(15) . . . . ? N42 C43 C44 C51 179.32(15) . . . . ? C54 C43 C44 C51 1.3(3) . . . . ? N45 C44 C51 C52 165.65(15) . . . . ? C43 C44 C51 C52 -16.5(2) . . . . ? N45 C44 C51 C512 -73.36(19) . . . . ? C43 C44 C51 C512 104.45(19) . . . . ? N45 C44 C51 C511 44.6(2) . . . . ? C43 C44 C51 C511 -137.57(17) . . . . ? C44 C51 C52 C53 45.9(2) . . . . ? C512 C51 C52 C53 -73.3(2) . . . . ? C511 C51 C52 C53 167.20(16) . . . . ? C51 C52 C53 C54 -63.0(2) . . . . ? N42 C43 C54 C541 -71.73(19) . . . . ? C44 C43 C54 C541 106.38(19) . . . . ? N42 C43 C54 C542 48.0(2) . . . . ? C44 C43 C54 C542 -133.89(17) . . . . ? N42 C43 C54 C53 167.53(14) . . . . ? C44 C43 C54 C53 -14.4(2) . . . . ? C52 C53 C54 C43 43.83(19) . . . . ? C52 C53 C54 C541 -75.6(2) . . . . ? C52 C53 C54 C542 164.56(15) . . . . ? _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.956 _refine_diff_density_max 0.306 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.054 _publ_section_references ; Oxford Diffraction Ltd, Crysalis Program (2005) Oxford Diffraction Ltd, Abspack Program (2005) Sheldrick, G.M. (1997) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (2004) PLATON program, Utrecht University, The Netherlands ; data_dw072bap-1 _database_code_depnum_ccdc_archive 'CCDC 869236' #TrackingRef '- CIF Files.txt' _audit_creation_date 2012-04-14 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _publ_section_comment ; the resiudal electron density within the structure, 2.72 and -1.18 eA^-3, is located near U1 and U2 There is no other residual electron density near anything else within the structure ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C27 H30 N6 O3 U), N4 O14 U' _chemical_formula_sum 'C54 H60 N16 O20 U3' _chemical_formula_weight 1966.70 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' U U -9.6770 9.6650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 11.1976(8) _cell_length_b 11.5470(8) _cell_length_c 13.3767(10) _cell_angle_alpha 113.4860(10) _cell_angle_beta 99.1500(10) _cell_angle_gamma 94.8080(10) _cell_volume 1545.29(19) _cell_formula_units_Z 1 _cell_measurement_reflns_used 4667 _cell_measurement_temperature 100.15 _cell_measurement_theta_max 26.355 _cell_measurement_theta_min 2.470 _exptl_absorpt_coefficient_mu 7.929 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.672654 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0595 before and 0.0214 after correction. The Ratio of minimum to maximum transmission is 0.6727. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 2.113 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 932 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_unetI/netI 0.0415 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 12300 _diffrn_reflns_theta_full 26.39 _diffrn_reflns_theta_max 26.39 _diffrn_reflns_theta_min 1.70 _diffrn_ambient_temperature 100.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Bruker SMART APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 40.0 _diffrn_source_power 1.6 _diffrn_source_voltage 40.0 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 5362 _reflns_number_total 6198 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection ? _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 2.718 _refine_diff_density_min -1.180 _refine_diff_density_rms 0.172 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 429 _refine_ls_number_reflns 6198 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0406 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+8.5800P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.0903 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 U2 U 0.42880(2) 0.48042(2) 0.25676(2) 0.02004(8) Uani 1 1 d . . . O9 O 0.3399(5) 0.3666(5) 0.1278(4) 0.0255(11) Uani 1 1 d . . . O10 O 0.5272(5) 0.5879(4) 0.3832(4) 0.0295(12) Uani 1 1 d . . . O8 O 0.2687(6) 0.5614(6) 0.2960(6) 0.0444(15) Uani 1 1 d D . . H2 H 0.282(3) 0.611(8) 0.368(2) 0.067 Uiso 1 1 d D . . N6 N 0.5675(5) 0.3118(5) 0.2530(5) 0.0180(11) Uani 1 1 d . . . N7 N 0.6161(5) 0.4815(5) 0.1669(5) 0.0216(12) Uani 1 1 d . . . N3 N 0.3671(5) 0.3297(5) 0.3401(5) 0.0206(12) Uani 1 1 d . . . N4 N 0.2664(5) 0.3453(5) 0.3840(5) 0.0221(13) Uani 1 1 d . . . N8 N 0.4498(6) 0.6384(5) 0.1707(5) 0.0249(13) Uani 1 1 d . . . N5 N 0.3958(5) 0.1519(5) 0.3822(5) 0.0194(12) Uani 1 1 d . . . C21 C 0.1311(8) 0.0882(7) 0.4978(7) 0.0325(18) Uani 1 1 d . . . H21A H 0.0717 0.0451 0.4256 0.039 Uiso 1 1 calc R . . H21B H 0.1143 0.0432 0.5446 0.039 Uiso 1 1 calc R . . C1 C 0.1424(10) 0.5311(13) 0.2548(12) 0.076(4) Uani 1 1 d D . . H1A H 0.1247 0.4621 0.1794 0.114 Uiso 1 1 calc R . . H1B H 0.1107 0.6067 0.2524 0.114 Uiso 1 1 calc R . . H1C H 0.1029 0.5030 0.3035 0.114 Uiso 1 1 calc R . . C26 C 0.2678(8) -0.0618(7) 0.3995(8) 0.037(2) Uani 1 1 d . . . H26A H 0.2522 -0.1182 0.4363 0.056 Uiso 1 1 calc R . . H26B H 0.3497 -0.0658 0.3825 0.056 Uiso 1 1 calc R . . H26C H 0.2063 -0.0894 0.3302 0.056 Uiso 1 1 calc R . . C27 C 0.3535(8) 0.1161(8) 0.5861(7) 0.0358(19) Uani 1 1 d . . . H27A H 0.3509 0.2051 0.6350 0.054 Uiso 1 1 calc R . . H27B H 0.4359 0.1085 0.5707 0.054 Uiso 1 1 calc R . . H27C H 0.3334 0.0608 0.6228 0.054 Uiso 1 1 calc R . . C4 C 0.4275(6) 0.2360(6) 0.3425(6) 0.0192(14) Uani 1 1 d . . . C9 C 0.5510(7) 0.6597(6) 0.1327(6) 0.0219(15) Uani 1 1 d . . . C6 C 0.6658(6) 0.3023(6) 0.2049(6) 0.0217(14) Uani 1 1 d . . . C17 C 0.7354(6) 0.2063(7) 0.1971(6) 0.0256(16) Uani 1 1 d . . . H17 H 0.8036 0.2003 0.1622 0.031 Uiso 1 1 calc R . . C20 C 0.2603(6) 0.0752(6) 0.4765(6) 0.0226(15) Uani 1 1 d . . . C3 C 0.2973(6) 0.1667(6) 0.4262(5) 0.0199(14) Uani 1 1 d . . . C5 C 0.5383(6) 0.2250(6) 0.2931(6) 0.0199(14) Uani 1 1 d . . . C7 C 0.6972(6) 0.4006(6) 0.1644(6) 0.0219(15) Uani 1 1 d . . . C10 C 0.3634(8) 0.7124(7) 0.1712(6) 0.0309(17) Uani 1 1 d . . . H10 H 0.2931 0.6986 0.1991 0.037 Uiso 1 1 calc R . . C13 C 0.5658(8) 0.7560(7) 0.0956(6) 0.0315(18) Uani 1 1 d . . . H13 H 0.6372 0.7706 0.0696 0.038 Uiso 1 1 calc R . . C2 C 0.2318(6) 0.2672(6) 0.4281(6) 0.0201(14) Uani 1 1 d . . . C18 C 0.7058(7) 0.1196(7) 0.2396(6) 0.0274(16) Uani 1 1 d . . . H18 H 0.7534 0.0539 0.2346 0.033 Uiso 1 1 calc R . . C12 C 0.4744(8) 0.8298(7) 0.0973(6) 0.0320(18) Uani 1 1 d . . . H12 H 0.4834 0.8965 0.0731 0.038 Uiso 1 1 calc R . . C19 C 0.6062(6) 0.1294(7) 0.2898(6) 0.0246(15) Uani 1 1 d . . . H19 H 0.5848 0.0719 0.3212 0.030 Uiso 1 1 calc R . . C15 C 0.8328(7) 0.5051(8) 0.0939(7) 0.0343(18) Uani 1 1 d . . . H15 H 0.9074 0.5140 0.0704 0.041 Uiso 1 1 calc R . . C24 C 0.0070(7) 0.2566(8) 0.3873(6) 0.0312(18) Uani 1 1 d . . . H24A H 0.0164 0.3045 0.3420 0.047 Uiso 1 1 calc R . . H24B H -0.0655 0.2756 0.4197 0.047 Uiso 1 1 calc R . . H24C H -0.0030 0.1647 0.3402 0.047 Uiso 1 1 calc R . . C16 C 0.8061(7) 0.4101(8) 0.1282(6) 0.0308(17) Uani 1 1 d . . . H16 H 0.8613 0.3517 0.1272 0.037 Uiso 1 1 calc R . . C22 C 0.1101(7) 0.2233(7) 0.5536(7) 0.0308(17) Uani 1 1 d . . . H22A H 0.1710 0.2680 0.6248 0.037 Uiso 1 1 calc R . . H22B H 0.0275 0.2234 0.5712 0.037 Uiso 1 1 calc R . . C8 C 0.6431(7) 0.5748(7) 0.1313(6) 0.0246(15) Uani 1 1 d . . . C23 C 0.1206(6) 0.2958(7) 0.4806(6) 0.0238(15) Uani 1 1 d . . . C11 C 0.3712(8) 0.8072(8) 0.1335(7) 0.0329(18) Uani 1 1 d . . . H11 H 0.3066 0.8554 0.1327 0.039 Uiso 1 1 calc R . . C14 C 0.7504(7) 0.5870(8) 0.0941(6) 0.0318(18) Uani 1 1 d . . . H14 H 0.7668 0.6516 0.0688 0.038 Uiso 1 1 calc R . . C25 C 0.1359(7) 0.4397(7) 0.5532(6) 0.0285(16) Uani 1 1 d . . . H25A H 0.2129 0.4670 0.6089 0.043 Uiso 1 1 calc R . . H25B H 0.0671 0.4578 0.5911 0.043 Uiso 1 1 calc R . . H25C H 0.1374 0.4865 0.5062 0.043 Uiso 1 1 calc R . . U1 U 0.0000 0.0000 0.0000 0.02291(10) Uani 1 2 d S . . O7 O 0.0182(5) -0.1576(5) -0.0833(4) 0.0301(12) Uani 1 1 d . . . O2 O 0.3819(5) 0.0851(5) 0.0631(5) 0.0361(13) Uani 1 1 d . . . O1 O 0.2013(5) 0.0785(5) -0.0319(4) 0.0302(12) Uani 1 1 d . . . O3 O -0.2145(5) -0.0410(5) -0.1143(4) 0.0319(12) Uani 1 1 d . . . O5 O -0.0248(9) 0.2362(8) -0.1115(8) 0.080(3) Uani 1 1 d . . . O4 O -0.0118(5) 0.0366(6) -0.1643(5) 0.0369(13) Uani 1 1 d . . . O6 O 0.0745(9) 0.1427(9) -0.2396(6) 0.100(4) Uani 1 1 d . . . N1 N 0.2708(6) 0.0703(6) 0.0497(5) 0.0286(14) Uani 1 1 d . . . N2 N 0.0136(8) 0.1418(9) -0.1712(7) 0.056(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U2 0.02548(15) 0.01638(13) 0.02178(14) 0.00917(10) 0.00994(11) 0.00628(10) O9 0.029(3) 0.023(3) 0.025(3) 0.011(2) 0.006(2) 0.002(2) O10 0.046(3) 0.017(2) 0.019(3) 0.002(2) 0.005(2) 0.002(2) O8 0.048(4) 0.048(4) 0.059(4) 0.034(3) 0.032(3) 0.025(3) N6 0.016(3) 0.015(3) 0.022(3) 0.007(2) 0.005(2) 0.004(2) N7 0.024(3) 0.023(3) 0.014(3) 0.004(2) 0.005(2) -0.001(2) N3 0.021(3) 0.021(3) 0.024(3) 0.010(2) 0.012(2) 0.008(2) N4 0.027(3) 0.024(3) 0.020(3) 0.012(3) 0.010(3) 0.014(3) N8 0.034(4) 0.019(3) 0.021(3) 0.009(2) 0.004(3) 0.003(3) N5 0.021(3) 0.016(3) 0.024(3) 0.009(2) 0.009(2) 0.002(2) C21 0.042(5) 0.021(4) 0.048(5) 0.022(4) 0.021(4) 0.017(3) C1 0.051(7) 0.094(10) 0.120(11) 0.075(9) 0.035(7) 0.026(6) C26 0.036(5) 0.026(4) 0.051(5) 0.016(4) 0.013(4) 0.004(3) C27 0.042(5) 0.037(5) 0.034(4) 0.025(4) 0.000(4) 0.000(4) C4 0.017(3) 0.018(3) 0.021(3) 0.007(3) 0.005(3) 0.003(3) C9 0.031(4) 0.014(3) 0.016(3) 0.003(3) 0.004(3) -0.004(3) C6 0.020(3) 0.021(3) 0.021(4) 0.006(3) 0.006(3) 0.002(3) C17 0.019(3) 0.026(4) 0.032(4) 0.011(3) 0.011(3) 0.005(3) C20 0.022(4) 0.017(3) 0.027(4) 0.008(3) 0.006(3) 0.001(3) C3 0.020(3) 0.020(3) 0.017(3) 0.005(3) 0.003(3) 0.001(3) C5 0.020(3) 0.018(3) 0.021(3) 0.008(3) 0.004(3) 0.002(3) C7 0.022(4) 0.019(3) 0.020(3) 0.005(3) 0.003(3) 0.003(3) C10 0.043(5) 0.024(4) 0.031(4) 0.013(3) 0.015(4) 0.009(3) C13 0.045(5) 0.022(4) 0.024(4) 0.007(3) 0.009(4) -0.001(3) C2 0.019(3) 0.023(3) 0.017(3) 0.007(3) 0.004(3) 0.004(3) C18 0.025(4) 0.020(4) 0.034(4) 0.008(3) 0.008(3) 0.007(3) C12 0.053(5) 0.019(4) 0.023(4) 0.009(3) 0.009(4) 0.001(3) C19 0.020(3) 0.025(4) 0.034(4) 0.016(3) 0.008(3) 0.008(3) C15 0.028(4) 0.047(5) 0.036(5) 0.023(4) 0.015(4) 0.011(4) C24 0.021(4) 0.039(4) 0.027(4) 0.007(3) 0.004(3) 0.007(3) C16 0.031(4) 0.037(4) 0.032(4) 0.019(4) 0.015(3) 0.009(3) C22 0.034(4) 0.035(4) 0.031(4) 0.017(4) 0.016(4) 0.010(3) C8 0.031(4) 0.023(4) 0.017(3) 0.008(3) 0.003(3) -0.004(3) C23 0.021(4) 0.030(4) 0.025(4) 0.014(3) 0.008(3) 0.009(3) C11 0.047(5) 0.028(4) 0.031(4) 0.017(3) 0.010(4) 0.014(4) C14 0.036(4) 0.032(4) 0.029(4) 0.014(3) 0.009(4) -0.001(3) C25 0.027(4) 0.035(4) 0.025(4) 0.012(3) 0.013(3) 0.011(3) U1 0.0280(2) 0.0262(2) 0.0219(2) 0.01341(16) 0.01207(16) 0.01307(16) O7 0.036(3) 0.025(3) 0.033(3) 0.010(2) 0.016(2) 0.014(2) O2 0.026(3) 0.032(3) 0.047(4) 0.014(3) 0.003(3) 0.004(2) O1 0.038(3) 0.033(3) 0.025(3) 0.017(2) 0.010(2) 0.007(2) O3 0.027(3) 0.048(3) 0.030(3) 0.025(3) 0.007(2) 0.010(2) O5 0.113(8) 0.044(5) 0.085(6) 0.038(5) 0.001(5) 0.006(5) O4 0.040(3) 0.047(4) 0.032(3) 0.026(3) 0.006(3) 0.004(3) O6 0.131(8) 0.116(7) 0.033(4) 0.029(5) 0.017(5) -0.068(6) N1 0.035(4) 0.021(3) 0.030(3) 0.010(3) 0.004(3) 0.010(3) N2 0.068(6) 0.056(5) 0.035(4) 0.028(4) -0.014(4) -0.029(5) _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 U2 O9 1.767(5) . ? U2 O10 1.766(5) . ? U2 O8 2.134(6) . ? U2 H2 2.56(4) . ? U2 N6 2.580(5) . ? U2 N7 2.579(6) . ? U2 N3 2.517(6) . ? U2 N8 2.529(6) . ? O8 H2 0.879(10) . ? O8 C1 1.393(13) . ? N6 C6 1.352(8) . ? N6 C5 1.352(8) . ? N7 C7 1.351(9) . ? N7 C8 1.371(9) . ? N3 N4 1.345(8) . ? N3 C4 1.332(8) . ? N4 C2 1.323(9) . ? N8 C9 1.356(9) . ? N8 C10 1.343(10) . ? N5 C4 1.329(8) . ? N5 C3 1.323(8) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C20 1.526(10) . ? C21 C22 1.495(10) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C26 C20 1.523(10) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C27 C20 1.530(10) . ? C4 C5 1.487(9) . ? C9 C13 1.394(10) . ? C9 C8 1.478(10) . ? C6 C17 1.388(10) . ? C6 C7 1.479(10) . ? C17 H17 0.9500 . ? C17 C18 1.376(10) . ? C20 C3 1.524(9) . ? C3 C2 1.418(9) . ? C5 C19 1.383(9) . ? C7 C16 1.394(10) . ? C10 H10 0.9500 . ? C10 C11 1.378(10) . ? C13 H13 0.9500 . ? C13 C12 1.383(11) . ? C2 C23 1.521(9) . ? C18 H18 0.9500 . ? C18 C19 1.380(10) . ? C12 H12 0.9500 . ? C12 C11 1.367(11) . ? C19 H19 0.9500 . ? C15 H15 0.9500 . ? C15 C16 1.375(11) . ? C15 C14 1.375(11) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C24 C23 1.526(10) . ? C16 H16 0.9500 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C22 C23 1.530(10) . ? C8 C14 1.390(10) . ? C23 C25 1.533(10) . ? C11 H11 0.9500 . ? C14 H14 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? U1 O7 1.764(5) . ? U1 O7 1.764(5) 2 ? U1 O1 2.521(5) 2 ? U1 O1 2.521(5) . ? U1 O3 2.529(5) . ? U1 O3 2.529(5) 2 ? U1 O4 2.384(5) 2 ? U1 O4 2.384(5) . ? O2 N1 1.216(8) . ? O1 N1 1.276(8) . ? O3 N1 1.276(8) 2 ? O5 N2 1.226(12) . ? O4 N2 1.268(9) . ? O6 N2 1.228(11) . ? N1 O3 1.276(8) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O9 U2 O8 89.4(2) . . ? O9 U2 H2 107.6(6) . . ? O9 U2 N6 88.0(2) . . ? O9 U2 N7 90.4(2) . . ? O9 U2 N3 87.4(2) . . ? O9 U2 N8 89.1(2) . . ? O10 U2 O9 175.6(2) . . ? O10 U2 O8 95.0(3) . . ? O10 U2 H2 76.7(5) . . ? O10 U2 N6 88.0(2) . . ? O10 U2 N7 86.1(2) . . ? O10 U2 N3 92.5(2) . . ? O10 U2 N8 91.8(2) . . ? O8 U2 H2 18.9(7) . . ? O8 U2 N6 149.9(2) . . ? O8 U2 N7 147.0(2) . . ? O8 U2 N3 86.7(2) . . ? O8 U2 N8 83.3(2) . . ? N6 U2 H2 142(2) . . ? N7 U2 H2 147(2) . . ? N7 U2 N6 63.05(18) . . ? N3 U2 H2 83(2) . . ? N3 U2 N6 63.27(17) . . ? N3 U2 N7 126.32(18) . . ? N3 U2 N8 169.36(19) . . ? N8 U2 H2 89(2) . . ? N8 U2 N6 126.65(19) . . ? N8 U2 N7 63.72(19) . . ? U2 O8 H2 109(3) . . ? C1 O8 U2 138.2(7) . . ? C1 O8 H2 108(2) . . ? C6 N6 U2 121.4(4) . . ? C6 N6 C5 118.3(6) . . ? C5 N6 U2 120.2(4) . . ? C7 N7 U2 121.8(4) . . ? C7 N7 C8 117.9(6) . . ? C8 N7 U2 119.9(5) . . ? N4 N3 U2 117.4(4) . . ? C4 N3 U2 124.0(4) . . ? C4 N3 N4 118.6(6) . . ? C2 N4 N3 118.6(6) . . ? C9 N8 U2 122.3(5) . . ? C10 N8 U2 119.3(5) . . ? C10 N8 C9 118.1(6) . . ? C3 N5 C4 116.1(6) . . ? H21A C21 H21B 107.6 . . ? C20 C21 H21A 108.7 . . ? C20 C21 H21B 108.7 . . ? C22 C21 H21A 108.7 . . ? C22 C21 H21B 108.7 . . ? C22 C21 C20 114.3(6) . . ? O8 C1 H1A 109.5 . . ? O8 C1 H1B 109.5 . . ? O8 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? H26A C26 H26B 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C20 C26 H26A 109.5 . . ? C20 C26 H26B 109.5 . . ? C20 C26 H26C 109.5 . . ? H27A C27 H27B 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C20 C27 H27A 109.5 . . ? C20 C27 H27B 109.5 . . ? C20 C27 H27C 109.5 . . ? N3 C4 C5 115.6(6) . . ? N5 C4 N3 125.9(6) . . ? N5 C4 C5 118.5(6) . . ? N8 C9 C13 121.2(7) . . ? N8 C9 C8 116.6(6) . . ? C13 C9 C8 122.2(7) . . ? N6 C6 C17 121.0(6) . . ? N6 C6 C7 117.0(6) . . ? C17 C6 C7 122.0(6) . . ? C6 C17 H17 119.9 . . ? C18 C17 C6 120.2(7) . . ? C18 C17 H17 119.9 . . ? C21 C20 C27 110.8(7) . . ? C26 C20 C21 111.3(6) . . ? C26 C20 C27 109.2(6) . . ? C26 C20 C3 110.4(6) . . ? C3 C20 C21 109.1(6) . . ? C3 C20 C27 105.9(6) . . ? N5 C3 C20 117.8(6) . . ? N5 C3 C2 120.0(6) . . ? C2 C3 C20 122.2(6) . . ? N6 C5 C4 116.9(6) . . ? N6 C5 C19 123.0(6) . . ? C19 C5 C4 120.1(6) . . ? N7 C7 C6 116.4(6) . . ? N7 C7 C16 122.3(7) . . ? C16 C7 C6 121.3(6) . . ? N8 C10 H10 118.3 . . ? N8 C10 C11 123.5(8) . . ? C11 C10 H10 118.3 . . ? C9 C13 H13 120.6 . . ? C12 C13 C9 118.8(7) . . ? C12 C13 H13 120.6 . . ? N4 C2 C3 120.8(6) . . ? N4 C2 C23 115.0(6) . . ? C3 C2 C23 124.2(6) . . ? C17 C18 H18 120.4 . . ? C17 C18 C19 119.2(7) . . ? C19 C18 H18 120.4 . . ? C13 C12 H12 119.9 . . ? C11 C12 C13 120.2(7) . . ? C11 C12 H12 119.9 . . ? C5 C19 H19 120.9 . . ? C18 C19 C5 118.3(7) . . ? C18 C19 H19 120.9 . . ? C16 C15 H15 120.3 . . ? C16 C15 C14 119.4(7) . . ? C14 C15 H15 120.3 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? C7 C16 H16 120.4 . . ? C15 C16 C7 119.2(7) . . ? C15 C16 H16 120.4 . . ? C21 C22 H22A 109.2 . . ? C21 C22 H22B 109.2 . . ? C21 C22 C23 112.0(6) . . ? H22A C22 H22B 107.9 . . ? C23 C22 H22A 109.2 . . ? C23 C22 H22B 109.2 . . ? N7 C8 C9 116.5(6) . . ? N7 C8 C14 121.5(7) . . ? C14 C8 C9 122.0(7) . . ? C2 C23 C24 108.4(6) . . ? C2 C23 C22 109.7(6) . . ? C2 C23 C25 109.2(6) . . ? C24 C23 C22 111.4(6) . . ? C24 C23 C25 109.1(6) . . ? C22 C23 C25 109.0(6) . . ? C10 C11 H11 120.9 . . ? C12 C11 C10 118.1(7) . . ? C12 C11 H11 120.9 . . ? C15 C14 C8 119.7(7) . . ? C15 C14 H14 120.1 . . ? C8 C14 H14 120.1 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O7 U1 O7 180.0 2 . ? O7 U1 O1 88.4(2) . . ? O7 U1 O1 88.4(2) 2 2 ? O7 U1 O1 91.6(2) . 2 ? O7 U1 O1 91.6(2) 2 . ? O7 U1 O3 89.7(2) . . ? O7 U1 O3 90.3(2) 2 . ? O7 U1 O3 89.7(2) 2 2 ? O7 U1 O3 90.3(2) . 2 ? O7 U1 O4 93.7(2) 2 . ? O7 U1 O4 93.7(2) . 2 ? O7 U1 O4 86.3(2) 2 2 ? O7 U1 O4 86.3(2) . . ? O1 U1 O1 180.0 2 . ? O1 U1 O3 50.42(16) 2 . ? O1 U1 O3 129.58(16) . . ? O1 U1 O3 129.58(16) 2 2 ? O1 U1 O3 50.42(16) . 2 ? O3 U1 O3 180.0 . 2 ? O4 U1 O1 115.59(18) 2 . ? O4 U1 O1 115.59(18) . 2 ? O4 U1 O1 64.41(18) 2 2 ? O4 U1 O1 64.41(18) . . ? O4 U1 O3 114.81(18) 2 . ? O4 U1 O3 65.19(18) . . ? O4 U1 O3 114.81(18) . 2 ? O4 U1 O3 65.19(18) 2 2 ? O4 U1 O4 180.0 2 . ? N1 O1 U1 97.4(4) . . ? N1 O3 U1 97.0(4) 2 . ? N2 O4 U1 128.0(5) . . ? O2 N1 O1 122.8(7) . . ? O2 N1 O3 122.3(6) . 2 ? O1 N1 O3 114.8(6) . 2 ? O5 N2 O4 119.1(9) . . ? O5 N2 O6 123.4(10) . . ? O6 N2 O4 117.4(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag U2 N6 C6 C17 -175.9(5) . . . . ? U2 N6 C6 C7 5.8(8) . . . . ? U2 N6 C5 C4 -2.5(8) . . . . ? U2 N6 C5 C19 177.6(5) . . . . ? U2 N7 C7 C6 6.4(8) . . . . ? U2 N7 C7 C16 -172.2(5) . . . . ? U2 N7 C8 C9 -8.4(8) . . . . ? U2 N7 C8 C14 172.7(5) . . . . ? U2 N3 N4 C2 179.9(5) . . . . ? U2 N3 C4 N5 -177.6(5) . . . . ? U2 N3 C4 C5 0.8(8) . . . . ? U2 N8 C9 C13 -173.7(5) . . . . ? U2 N8 C9 C8 7.2(8) . . . . ? U2 N8 C10 C11 175.3(6) . . . . ? O9 U2 O8 C1 11.2(9) . . . . ? O9 U2 N6 C6 89.6(5) . . . . ? O9 U2 N6 C5 -86.1(5) . . . . ? O9 U2 N7 C7 -90.1(5) . . . . ? O9 U2 N7 C8 97.2(5) . . . . ? O9 U2 N3 N4 -92.0(5) . . . . ? O9 U2 N3 C4 87.6(6) . . . . ? O9 U2 N8 C9 -98.9(5) . . . . ? O9 U2 N8 C10 87.2(6) . . . . ? O10 U2 O8 C1 -168.4(9) . . . . ? O10 U2 N6 C6 -88.6(5) . . . . ? O10 U2 N6 C5 95.8(5) . . . . ? O10 U2 N7 C7 87.2(5) . . . . ? O10 U2 N7 C8 -85.5(5) . . . . ? O10 U2 N3 N4 92.4(5) . . . . ? O10 U2 N3 C4 -88.0(6) . . . . ? O10 U2 N8 C9 76.8(5) . . . . ? O10 U2 N8 C10 -97.1(6) . . . . ? O8 U2 N6 C6 174.9(5) . . . . ? O8 U2 N6 C5 -0.7(7) . . . . ? O8 U2 N7 C7 -179.7(5) . . . . ? O8 U2 N7 C8 7.7(7) . . . . ? O8 U2 N3 N4 -2.4(5) . . . . ? O8 U2 N3 C4 177.2(6) . . . . ? O8 U2 N8 C9 171.5(5) . . . . ? O8 U2 N8 C10 -2.3(6) . . . . ? N6 U2 O8 C1 -73.8(10) . . . . ? N6 U2 N7 C7 -2.6(5) . . . . ? N6 U2 N7 C8 -175.3(5) . . . . ? N6 U2 N3 N4 179.0(5) . . . . ? N6 U2 N3 C4 -1.4(5) . . . . ? N6 U2 N8 C9 -12.1(6) . . . . ? N6 U2 N8 C10 174.0(5) . . . . ? N6 C6 C17 C18 -0.7(11) . . . . ? N6 C6 C7 N7 -7.8(9) . . . . ? N6 C6 C7 C16 170.8(7) . . . . ? N6 C5 C19 C18 -2.3(11) . . . . ? N7 U2 O8 C1 101.1(9) . . . . ? N7 U2 N6 C6 -1.9(5) . . . . ? N7 U2 N6 C5 -177.6(5) . . . . ? N7 U2 N3 N4 179.4(4) . . . . ? N7 U2 N3 C4 -1.0(6) . . . . ? N7 U2 N8 C9 -8.0(5) . . . . ? N7 U2 N8 C10 178.1(6) . . . . ? N7 C7 C16 C15 0.1(12) . . . . ? N7 C8 C14 C15 -0.9(11) . . . . ? N3 U2 O8 C1 -76.2(9) . . . . ? N3 U2 N6 C6 177.7(6) . . . . ? N3 U2 N6 C5 2.0(5) . . . . ? N3 U2 N7 C7 -3.0(6) . . . . ? N3 U2 N7 C8 -175.7(5) . . . . ? N3 U2 N8 C9 -169.8(8) . . . . ? N3 U2 N8 C10 16.3(13) . . . . ? N3 N4 C2 C3 -1.9(10) . . . . ? N3 N4 C2 C23 177.3(6) . . . . ? N3 C4 C5 N6 1.2(9) . . . . ? N3 C4 C5 C19 -178.9(6) . . . . ? N4 N3 C4 N5 2.0(11) . . . . ? N4 N3 C4 C5 -179.6(6) . . . . ? N4 C2 C23 C24 72.7(8) . . . . ? N4 C2 C23 C22 -165.5(6) . . . . ? N4 C2 C23 C25 -46.0(8) . . . . ? N8 U2 O8 C1 100.4(9) . . . . ? N8 U2 N6 C6 2.2(6) . . . . ? N8 U2 N6 C5 -173.5(5) . . . . ? N8 U2 N7 C7 -178.9(6) . . . . ? N8 U2 N7 C8 8.4(5) . . . . ? N8 U2 N3 N4 -21.0(13) . . . . ? N8 U2 N3 C4 158.6(9) . . . . ? N8 C9 C13 C12 -0.4(11) . . . . ? N8 C9 C8 N7 1.0(9) . . . . ? N8 C9 C8 C14 179.9(7) . . . . ? N8 C10 C11 C12 -2.4(12) . . . . ? N5 C4 C5 N6 179.7(6) . . . . ? N5 C4 C5 C19 -0.4(10) . . . . ? N5 C3 C2 N4 1.5(10) . . . . ? N5 C3 C2 C23 -177.5(6) . . . . ? C21 C20 C3 N5 -167.1(6) . . . . ? C21 C20 C3 C2 14.5(9) . . . . ? C21 C22 C23 C2 -44.1(9) . . . . ? C21 C22 C23 C24 76.0(8) . . . . ? C21 C22 C23 C25 -163.6(7) . . . . ? C26 C20 C3 N5 -44.5(9) . . . . ? C26 C20 C3 C2 137.1(7) . . . . ? C27 C20 C3 N5 73.5(8) . . . . ? C27 C20 C3 C2 -104.8(8) . . . . ? C4 N3 N4 C2 0.2(9) . . . . ? C4 N5 C3 C20 -177.9(6) . . . . ? C4 N5 C3 C2 0.6(9) . . . . ? C4 C5 C19 C18 177.7(7) . . . . ? C9 N8 C10 C11 1.2(11) . . . . ? C9 C13 C12 C11 -0.8(11) . . . . ? C9 C8 C14 C15 -179.6(7) . . . . ? C6 N6 C5 C4 -178.3(6) . . . . ? C6 N6 C5 C19 1.8(10) . . . . ? C6 C17 C18 C19 0.2(11) . . . . ? C6 C7 C16 C15 -178.4(7) . . . . ? C17 C6 C7 N7 173.9(6) . . . . ? C17 C6 C7 C16 -7.5(11) . . . . ? C17 C18 C19 C5 1.3(11) . . . . ? C20 C21 C22 C23 64.6(9) . . . . ? C20 C3 C2 N4 179.8(6) . . . . ? C20 C3 C2 C23 0.8(10) . . . . ? C3 N5 C4 N3 -2.3(10) . . . . ? C3 N5 C4 C5 179.3(6) . . . . ? C3 C2 C23 C24 -108.2(8) . . . . ? C3 C2 C23 C22 13.6(10) . . . . ? C3 C2 C23 C25 133.0(7) . . . . ? C5 N6 C6 C17 -0.2(10) . . . . ? C5 N6 C6 C7 -178.5(6) . . . . ? C7 N7 C8 C9 178.6(6) . . . . ? C7 N7 C8 C14 -0.2(10) . . . . ? C7 C6 C17 C18 177.5(7) . . . . ? C10 N8 C9 C13 0.3(10) . . . . ? C10 N8 C9 C8 -178.9(6) . . . . ? C13 C9 C8 N7 -178.1(6) . . . . ? C13 C9 C8 C14 0.7(11) . . . . ? C13 C12 C11 C10 2.1(12) . . . . ? C16 C15 C14 C8 1.6(12) . . . . ? C22 C21 C20 C26 -168.5(7) . . . . ? C22 C21 C20 C27 69.7(8) . . . . ? C22 C21 C20 C3 -46.5(9) . . . . ? C8 N7 C7 C6 179.2(6) . . . . ? C8 N7 C7 C16 0.6(10) . . . . ? C8 C9 C13 C12 178.7(7) . . . . ? C14 C15 C16 C7 -1.2(12) . . . . ? U1 O1 N1 O2 171.5(6) . . . . ? U1 O1 N1 O3 -6.2(6) . . . 2 ? U1 O4 N2 O5 -45.9(12) . . . . ? U1 O4 N2 O6 135.2(7) . . . . ? O7 U1 O1 N1 -87.9(4) . . . . ? O7 U1 O1 N1 92.1(4) 2 . . . ? O7 U1 O3 N1 96.0(4) . . . 2 ? O7 U1 O3 N1 -84.0(4) 2 . . 2 ? O7 U1 O4 N2 -154.6(8) . . . . ? O7 U1 O4 N2 25.4(8) 2 . . . ? O1 U1 O1 N1 152(4) 2 . . . ? O1 U1 O3 N1 -176.3(4) . . . 2 ? O1 U1 O3 N1 3.7(4) 2 . . 2 ? O1 U1 O4 N2 115.4(7) 2 . . . ? O1 U1 O4 N2 -64.6(7) . . . . ? O3 U1 O1 N1 -176.3(4) . . . . ? O3 U1 O1 N1 3.7(4) 2 . . . ? O3 U1 O3 N1 170(3) 2 . . 2 ? O3 U1 O4 N2 -66.0(8) 2 . . . ? O3 U1 O4 N2 114.0(8) . . . . ? O4 U1 O1 N1 5.4(4) 2 . . . ? O4 U1 O1 N1 -174.6(4) . . . . ? O4 U1 O3 N1 2.1(5) 2 . . 2 ? O4 U1 O3 N1 -177.9(5) . . . 2 ? O4 U1 O4 N2 -14(7) 2 . . . ?