# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Eu_enbpy2_NO3_PF6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H23 Eu F6 N9 O6 P' _chemical_formula_weight 854.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 8.9999(9) _cell_length_b 12.2528(12) _cell_length_c 16.2526(16) _cell_angle_alpha 112.3060(10) _cell_angle_beta 104.4460(10) _cell_angle_gamma 91.8160(10) _cell_volume 1589.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 5208 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.56 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.785 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 2.114 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7421 _exptl_absorpt_correction_T_max 0.8491 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 17991 _diffrn_reflns_av_R_equivalents 0.0220 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 27.62 _reflns_number_total 7144 _reflns_number_gt 6613 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ISOR restraints for F3 and F4 atoms of the PF6 anion were used in order to address non-positive-definite errors. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0525P)^2^+4.6420P] 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 7144 _refine_ls_number_parameters 443 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0387 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.129 _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 C1 C 0.5208(5) 0.5731(4) 0.2554(3) 0.0200(8) Uani 1 1 d . . . H1 H 0.5034 0.5275 0.2890 0.024 Uiso 1 1 calc R . . C2 C 0.4613(5) 0.6797(4) 0.2728(3) 0.0230(8) Uani 1 1 d . . . H2 H 0.4036 0.7062 0.3166 0.028 Uiso 1 1 calc R . . C3 C 0.4877(5) 0.7467(4) 0.2248(3) 0.0268(9) Uani 1 1 d . . . H3 H 0.4520 0.8219 0.2370 0.032 Uiso 1 1 calc R . . C4 C 0.5666(5) 0.7032(4) 0.1587(3) 0.0230(8) Uani 1 1 d . . . H4 H 0.5829 0.7471 0.1238 0.028 Uiso 1 1 calc R . . C5 C 0.6220(4) 0.5944(4) 0.1439(3) 0.0174(8) Uani 1 1 d . . . C6 C 0.7018(4) 0.5391(4) 0.0716(3) 0.0174(8) Uani 1 1 d . . . C7 C 0.7254(5) 0.5929(4) 0.0128(3) 0.0216(8) Uani 1 1 d . . . H7 H 0.6976 0.6698 0.0214 0.026 Uiso 1 1 calc R . . C8 C 0.7897(5) 0.5327(4) -0.0580(3) 0.0238(9) Uani 1 1 d . . . H8 H 0.8053 0.5672 -0.0991 0.029 Uiso 1 1 calc R . . C9 C 0.8311(5) 0.4211(4) -0.0682(3) 0.0226(8) Uani 1 1 d . . . H9 H 0.8727 0.3768 -0.1172 0.027 Uiso 1 1 calc R . . C10 C 0.8101(5) 0.3762(4) -0.0050(3) 0.0193(8) Uani 1 1 d . . . C11 C 0.8535(5) 0.2591(4) -0.0108(3) 0.0219(8) Uani 1 1 d . . . H11 H 0.8856 0.2088 -0.0623 0.026 Uiso 1 1 calc R . . C12 C 0.8833(5) 0.1070(4) 0.0457(3) 0.0253(9) Uani 1 1 d . . . H12A H 0.9864 0.1131 0.0882 0.030 Uiso 1 1 calc R . . H12B H 0.8846 0.0579 -0.0185 0.030 Uiso 1 1 calc R . . C13 C 0.7578(6) 0.0503(4) 0.0710(3) 0.0267(9) Uani 1 1 d . . . H13A H 0.6567 0.0350 0.0239 0.032 Uiso 1 1 calc R . . H13B H 0.7839 -0.0263 0.0737 0.032 Uiso 1 1 calc R . . C14 C 0.7445(5) 0.0956(4) 0.2233(3) 0.0236(9) Uani 1 1 d . . . H14 H 0.7413 0.0129 0.2096 0.028 Uiso 1 1 calc R . . C15 C 0.7432(5) 0.1800(4) 0.3161(3) 0.0213(8) Uani 1 1 d . . . C16 C 0.7222(6) 0.1404(4) 0.3828(3) 0.0292(10) Uani 1 1 d . . . H16 H 0.7105 0.0578 0.3703 0.035 Uiso 1 1 calc R . . C17 C 0.7191(6) 0.2252(5) 0.4680(3) 0.0322(10) Uani 1 1 d . . . H17 H 0.7014 0.2012 0.5143 0.039 Uiso 1 1 calc R . . C18 C 0.7418(5) 0.3448(4) 0.4849(3) 0.0266(9) Uani 1 1 d . . . H18 H 0.7405 0.4037 0.5430 0.032 Uiso 1 1 calc R . . C19 C 0.7666(5) 0.3781(4) 0.4154(3) 0.0205(8) Uani 1 1 d . . . C20 C 0.8030(5) 0.5042(4) 0.4298(3) 0.0192(8) Uani 1 1 d . . . C21 C 0.8110(5) 0.5987(4) 0.5134(3) 0.0265(9) Uani 1 1 d . . . H21 H 0.7874 0.5843 0.5625 0.032 Uiso 1 1 calc R . . C22 C 0.8536(6) 0.7138(4) 0.5238(3) 0.0307(10) Uani 1 1 d . . . H22 H 0.8597 0.7794 0.5803 0.037 Uiso 1 1 calc R . . C23 C 0.8870(5) 0.7324(4) 0.4517(3) 0.0266(9) Uani 1 1 d . . . H23 H 0.9167 0.8107 0.4574 0.032 Uiso 1 1 calc R . . C24 C 0.8764(5) 0.6345(4) 0.3706(3) 0.0218(8) Uani 1 1 d . . . H24 H 0.9001 0.6475 0.3210 0.026 Uiso 1 1 calc R . . C25 C 0.3643(5) 0.0562(4) 0.2087(3) 0.0287(10) Uani 1 1 d . . . C26 C 0.3109(7) 0.1487(5) 0.2778(4) 0.0391(12) Uani 1 1 d . . . H26A H 0.3497 0.1438 0.3381 0.059 Uiso 1 1 calc R . . H26B H 0.1973 0.1376 0.2596 0.059 Uiso 1 1 calc R . . H26C H 0.3496 0.2270 0.2824 0.059 Uiso 1 1 calc R . . Eu1 Eu 0.75775(2) 0.352895(16) 0.191455(12) 0.01430(7) Uani 1 1 d . . . F1 F 0.0436(5) 1.0178(3) 0.3205(3) 0.0678(13) Uani 1 1 d . . . F2 F -0.0476(7) 0.8742(6) 0.1821(3) 0.1004(18) Uani 1 1 d . . . F3 F 0.0070(7) 0.7366(4) 0.2342(4) 0.0901(15) Uani 1 1 d U . . F4 F 0.1076(6) 0.8752(6) 0.3779(4) 0.0967(16) Uani 1 1 d U . . F5 F -0.1307(4) 0.8722(3) 0.3004(3) 0.0509(9) Uani 1 1 d . . . F6 F 0.1962(5) 0.8822(4) 0.2618(4) 0.0752(14) Uani 1 1 d . . . N1 N 0.6017(4) 0.5305(3) 0.1938(2) 0.0169(6) Uani 1 1 d . . . N2 N 0.7462(4) 0.4336(3) 0.0643(2) 0.0164(6) Uani 1 1 d . . . N3 N 0.8475(4) 0.2259(3) 0.0538(2) 0.0204(7) Uani 1 1 d . . . N4 N 0.7497(4) 0.1343(3) 0.1620(2) 0.0210(7) Uani 1 1 d . . . N5 N 0.7643(4) 0.2966(3) 0.3316(2) 0.0185(7) Uani 1 1 d . . . N6 N 0.8344(4) 0.5222(3) 0.3584(2) 0.0182(7) Uani 1 1 d . . . N7 N 0.4266(4) 0.2565(3) 0.1197(2) 0.0196(7) Uani 1 1 d . . . N8 N 1.0952(4) 0.4167(3) 0.2571(2) 0.0203(7) Uani 1 1 d . . . N9 N 0.4067(5) -0.0170(4) 0.1555(3) 0.0359(10) Uani 1 1 d . . . O1 O 0.5094(3) 0.2482(3) 0.0647(2) 0.0213(6) Uani 1 1 d . . . O2 O 0.4982(3) 0.3028(3) 0.20613(19) 0.0205(6) Uani 1 1 d . . . O3 O 0.2874(3) 0.2225(3) 0.0913(2) 0.0258(7) Uani 1 1 d . . . O4 O 1.0282(3) 0.3273(3) 0.2621(2) 0.0222(6) Uani 1 1 d . . . O5 O 1.0102(3) 0.4694(3) 0.2129(2) 0.0210(6) Uani 1 1 d . . . O6 O 1.2342(3) 0.4521(3) 0.2948(2) 0.0286(7) Uani 1 1 d . . . P1 P 0.03566(18) 0.87955(12) 0.28389(11) 0.0362(3) 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 C1 0.0207(19) 0.022(2) 0.0172(19) 0.0071(16) 0.0069(16) 0.0027(16) C2 0.020(2) 0.026(2) 0.022(2) 0.0062(17) 0.0094(16) 0.0080(16) C3 0.029(2) 0.019(2) 0.032(2) 0.0091(18) 0.0093(19) 0.0085(17) C4 0.022(2) 0.022(2) 0.028(2) 0.0134(18) 0.0069(17) 0.0053(16) C5 0.0163(18) 0.0190(19) 0.0156(18) 0.0071(15) 0.0021(15) -0.0005(15) C6 0.0130(17) 0.0221(19) 0.0154(18) 0.0074(15) 0.0015(14) -0.0002(14) C7 0.0188(19) 0.025(2) 0.022(2) 0.0129(17) 0.0015(16) 0.0001(16) C8 0.022(2) 0.034(2) 0.0182(19) 0.0153(18) 0.0039(16) 0.0015(17) C9 0.0188(19) 0.034(2) 0.0153(19) 0.0094(17) 0.0055(15) 0.0026(17) C10 0.0150(18) 0.025(2) 0.0139(18) 0.0043(16) 0.0035(14) 0.0016(15) C11 0.0201(19) 0.027(2) 0.0126(18) 0.0022(16) 0.0042(15) 0.0045(16) C12 0.032(2) 0.020(2) 0.020(2) 0.0038(17) 0.0072(18) 0.0141(18) C13 0.036(2) 0.018(2) 0.022(2) 0.0054(17) 0.0054(18) 0.0085(18) C14 0.025(2) 0.0176(19) 0.026(2) 0.0079(17) 0.0049(17) 0.0041(16) C15 0.022(2) 0.022(2) 0.022(2) 0.0122(17) 0.0048(16) 0.0060(16) C16 0.035(3) 0.027(2) 0.030(2) 0.017(2) 0.009(2) 0.0032(19) C17 0.040(3) 0.038(3) 0.027(2) 0.020(2) 0.012(2) 0.005(2) C18 0.033(2) 0.032(2) 0.017(2) 0.0109(18) 0.0087(18) 0.0057(19) C19 0.0194(19) 0.026(2) 0.0168(19) 0.0094(16) 0.0041(15) 0.0033(16) C20 0.0187(19) 0.022(2) 0.0144(18) 0.0055(16) 0.0028(15) 0.0020(15) C21 0.033(2) 0.029(2) 0.016(2) 0.0043(17) 0.0104(18) 0.0044(18) C22 0.040(3) 0.025(2) 0.020(2) -0.0013(18) 0.0124(19) 0.0040(19) C23 0.030(2) 0.019(2) 0.024(2) 0.0016(17) 0.0080(18) -0.0011(17) C24 0.025(2) 0.022(2) 0.0177(19) 0.0061(16) 0.0070(16) 0.0025(16) C25 0.028(2) 0.034(3) 0.032(2) 0.021(2) 0.009(2) 0.0027(19) C26 0.042(3) 0.041(3) 0.052(3) 0.028(3) 0.028(3) 0.014(2) Eu1 0.01612(11) 0.01498(11) 0.01151(10) 0.00470(7) 0.00415(7) 0.00379(7) F1 0.063(2) 0.0248(16) 0.115(4) 0.0117(19) 0.051(2) 0.0018(16) F2 0.129(5) 0.132(5) 0.052(3) 0.036(3) 0.043(3) 0.039(4) F3 0.106(3) 0.062(2) 0.113(3) 0.025(2) 0.065(2) 0.018(2) F4 0.080(3) 0.148(3) 0.085(3) 0.076(2) 0.016(2) 0.023(2) F5 0.048(2) 0.0462(19) 0.060(2) 0.0160(17) 0.0258(17) 0.0018(15) F6 0.071(3) 0.078(3) 0.134(4) 0.072(3) 0.076(3) 0.041(2) N1 0.0173(16) 0.0181(16) 0.0151(15) 0.0063(13) 0.0047(13) 0.0033(13) N2 0.0150(15) 0.0203(16) 0.0123(15) 0.0057(13) 0.0026(12) 0.0019(13) N3 0.0217(17) 0.0193(17) 0.0173(16) 0.0046(14) 0.0045(13) 0.0063(14) N4 0.0249(18) 0.0170(16) 0.0183(17) 0.0053(14) 0.0037(14) 0.0052(14) N5 0.0181(16) 0.0223(17) 0.0147(16) 0.0081(13) 0.0026(13) 0.0039(13) N6 0.0190(16) 0.0193(16) 0.0150(16) 0.0055(13) 0.0049(13) 0.0036(13) N7 0.0222(17) 0.0175(16) 0.0202(17) 0.0096(14) 0.0047(14) 0.0036(13) N8 0.0193(17) 0.0268(18) 0.0135(15) 0.0054(14) 0.0066(13) 0.0043(14) N9 0.041(2) 0.036(2) 0.030(2) 0.0139(19) 0.0074(19) 0.0012(19) O1 0.0236(15) 0.0235(15) 0.0172(14) 0.0078(12) 0.0073(12) 0.0037(12) O2 0.0221(14) 0.0217(14) 0.0168(14) 0.0071(12) 0.0049(11) 0.0026(11) O3 0.0187(15) 0.0263(16) 0.0305(17) 0.0125(13) 0.0022(13) -0.0011(12) O4 0.0221(15) 0.0249(15) 0.0216(15) 0.0112(12) 0.0064(12) 0.0051(12) O5 0.0231(14) 0.0245(15) 0.0174(14) 0.0100(12) 0.0062(11) 0.0051(12) O6 0.0162(14) 0.0422(19) 0.0237(16) 0.0104(14) 0.0045(12) -0.0008(13) P1 0.0516(8) 0.0277(6) 0.0502(8) 0.0229(6) 0.0365(7) 0.0192(6) _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 C1 N1 1.340(5) . ? C1 C2 1.383(6) . ? C1 H1 0.9500 . ? C2 C3 1.380(6) . ? C2 H2 0.9500 . ? C3 C4 1.382(6) . ? C3 H3 0.9500 . ? C4 C5 1.394(6) . ? C4 H4 0.9500 . ? C5 N1 1.359(5) . ? C5 C6 1.484(5) . ? C6 N2 1.336(5) . ? C6 C7 1.402(6) . ? C7 C8 1.386(6) . ? C7 H7 0.9500 . ? C8 C9 1.388(6) . ? C8 H8 0.9500 . ? C9 C10 1.383(6) . ? C9 H9 0.9500 . ? C10 N2 1.357(5) . ? C10 C11 1.473(6) . ? C11 N3 1.274(6) . ? C11 H11 0.9500 . ? C12 N3 1.466(5) . ? C12 C13 1.525(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.469(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.265(6) . ? C14 C15 1.473(6) . ? C14 H14 0.9500 . ? C15 N5 1.352(5) . ? C15 C16 1.393(6) . ? C16 C17 1.388(7) . ? C16 H16 0.9500 . ? C17 C18 1.383(7) . ? C17 H17 0.9500 . ? C18 C19 1.401(6) . ? C18 H18 0.9500 . ? C19 N5 1.343(5) . ? C19 C20 1.484(6) . ? C20 N6 1.352(5) . ? C20 C21 1.394(6) . ? C21 C22 1.385(7) . ? C21 H21 0.9500 . ? C22 C23 1.375(7) . ? C22 H22 0.9500 . ? C23 C24 1.384(6) . ? C23 H23 0.9500 . ? C24 N6 1.341(5) . ? C24 H24 0.9500 . ? C25 N9 1.139(7) . ? C25 C26 1.454(7) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? Eu1 O2 2.488(3) . ? Eu1 O4 2.503(3) . ? Eu1 O5 2.518(3) . ? Eu1 O1 2.530(3) . ? Eu1 N4 2.531(3) . ? Eu1 N3 2.533(3) . ? Eu1 N2 2.591(3) . ? Eu1 N5 2.607(3) . ? Eu1 N6 2.616(3) . ? Eu1 N1 2.621(3) . ? F1 P1 1.560(4) . ? F2 P1 1.612(5) . ? F3 P1 1.607(5) . ? F4 P1 1.525(5) . ? F5 P1 1.591(4) . ? F6 P1 1.576(4) . ? N7 O3 1.219(5) . ? N7 O2 1.277(4) . ? N7 O1 1.278(4) . ? N8 O6 1.229(5) . ? N8 O4 1.273(5) . ? N8 O5 1.275(5) . ? 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 N1 C1 C2 123.6(4) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C3 C2 C1 118.3(4) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 119.3(4) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C3 C4 C5 119.4(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 121.5(4) . . ? N1 C5 C6 115.8(3) . . ? C4 C5 C6 122.7(4) . . ? N2 C6 C7 121.9(4) . . ? N2 C6 C5 116.1(3) . . ? C7 C6 C5 122.0(4) . . ? C8 C7 C6 119.2(4) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 119.1(4) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 118.2(4) . . ? C10 C9 H9 120.9 . . ? C8 C9 H9 120.9 . . ? N2 C10 C9 123.4(4) . . ? N2 C10 C11 115.5(4) . . ? C9 C10 C11 121.1(4) . . ? N3 C11 C10 119.3(4) . . ? N3 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? N3 C12 C13 107.4(3) . . ? N3 C12 H12A 110.2 . . ? C13 C12 H12A 110.2 . . ? N3 C12 H12B 110.2 . . ? C13 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? N4 C13 C12 107.3(4) . . ? N4 C13 H13A 110.3 . . ? C12 C13 H13A 110.3 . . ? N4 C13 H13B 110.3 . . ? C12 C13 H13B 110.3 . . ? H13A C13 H13B 108.5 . . ? N4 C14 C15 119.4(4) . . ? N4 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? N5 C15 C16 123.0(4) . . ? N5 C15 C14 115.6(4) . . ? C16 C15 C14 121.3(4) . . ? C17 C16 C15 118.0(4) . . ? C17 C16 H16 121.0 . . ? C15 C16 H16 121.0 . . ? C18 C17 C16 119.5(4) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 119.3(4) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? N5 C19 C18 121.6(4) . . ? N5 C19 C20 115.5(4) . . ? C18 C19 C20 122.9(4) . . ? N6 C20 C21 121.7(4) . . ? N6 C20 C19 116.1(3) . . ? C21 C20 C19 122.2(4) . . ? C22 C21 C20 119.2(4) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C23 C22 C21 119.4(4) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 118.4(4) . . ? C22 C23 H23 120.8 . . ? C24 C23 H23 120.8 . . ? N6 C24 C23 123.4(4) . . ? N6 C24 H24 118.3 . . ? C23 C24 H24 118.3 . . ? N9 C25 C26 179.0(5) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O2 Eu1 O4 134.63(10) . . ? O2 Eu1 O5 161.19(10) . . ? O4 Eu1 O5 51.16(10) . . ? O2 Eu1 O1 51.15(9) . . ? O4 Eu1 O1 143.95(10) . . ? O5 Eu1 O1 138.72(9) . . ? O2 Eu1 N4 77.56(11) . . ? O4 Eu1 N4 74.04(11) . . ? O5 Eu1 N4 118.76(11) . . ? O1 Eu1 N4 74.05(10) . . ? O2 Eu1 N3 121.55(10) . . ? O4 Eu1 N3 75.81(10) . . ? O5 Eu1 N3 76.17(10) . . ? O1 Eu1 N3 75.70(10) . . ? N4 Eu1 N3 64.66(12) . . ? O2 Eu1 N2 113.35(10) . . ? O4 Eu1 N2 111.77(10) . . ? O5 Eu1 N2 66.94(10) . . ? O1 Eu1 N2 73.62(10) . . ? N4 Eu1 N2 123.63(11) . . ? N3 Eu1 N2 63.32(11) . . ? O2 Eu1 N5 65.43(10) . . ? O4 Eu1 N5 70.31(10) . . ? O5 Eu1 N5 111.88(10) . . ? O1 Eu1 N5 108.71(10) . . ? N4 Eu1 N5 63.00(11) . . ? N3 Eu1 N5 123.25(11) . . ? N2 Eu1 N5 173.24(10) . . ? O2 Eu1 N6 90.75(10) . . ? O4 Eu1 N6 76.19(10) . . ? O5 Eu1 N6 72.77(10) . . ? O1 Eu1 N6 136.58(10) . . ? N4 Eu1 N6 122.66(11) . . ? N3 Eu1 N6 146.99(11) . . ? N2 Eu1 N6 112.64(10) . . ? N5 Eu1 N6 61.18(11) . . ? O2 Eu1 N1 72.09(10) . . ? O4 Eu1 N1 137.07(10) . . ? O5 Eu1 N1 93.24(10) . . ? O1 Eu1 N1 77.94(10) . . ? N4 Eu1 N1 147.49(11) . . ? N3 Eu1 N1 123.37(11) . . ? N2 Eu1 N1 61.47(10) . . ? N5 Eu1 N1 112.43(10) . . ? N6 Eu1 N1 69.82(10) . . ? C1 N1 C5 117.8(3) . . ? C1 N1 Eu1 120.7(3) . . ? C5 N1 Eu1 120.6(3) . . ? C6 N2 C10 118.0(3) . . ? C6 N2 Eu1 122.4(3) . . ? C10 N2 Eu1 118.7(3) . . ? C11 N3 C12 119.2(4) . . ? C11 N3 Eu1 122.2(3) . . ? C12 N3 Eu1 118.4(3) . . ? C14 N4 C13 119.1(4) . . ? C14 N4 Eu1 122.7(3) . . ? C13 N4 Eu1 118.1(3) . . ? C19 N5 C15 118.5(4) . . ? C19 N5 Eu1 122.4(3) . . ? C15 N5 Eu1 118.5(3) . . ? C24 N6 C20 117.9(3) . . ? C24 N6 Eu1 119.6(3) . . ? C20 N6 Eu1 121.1(3) . . ? O3 N7 O2 122.0(3) . . ? O3 N7 O1 122.0(3) . . ? O2 N7 O1 116.0(3) . . ? O6 N8 O4 121.6(4) . . ? O6 N8 O5 121.7(4) . . ? O4 N8 O5 116.7(3) . . ? N7 O1 Eu1 95.4(2) . . ? N7 O2 Eu1 97.4(2) . . ? N8 O4 Eu1 96.2(2) . . ? N8 O5 Eu1 95.4(2) . . ? F4 P1 F1 96.3(3) . . ? F4 P1 F6 93.2(3) . . ? F1 P1 F6 92.7(2) . . ? F4 P1 F5 89.3(3) . . ? F1 P1 F5 88.9(2) . . ? F6 P1 F5 176.9(3) . . ? F4 P1 F3 91.0(3) . . ? F1 P1 F3 171.8(3) . . ? F6 P1 F3 90.4(3) . . ? F5 P1 F3 87.6(2) . . ? F4 P1 F2 175.6(4) . . ? F1 P1 F2 87.5(3) . . ? F6 P1 F2 88.8(3) . . ? F5 P1 F2 88.7(3) . . ? F3 P1 F2 85.0(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.7(7) . . . . ? C1 C2 C3 C4 2.6(7) . . . . ? C2 C3 C4 C5 -1.9(7) . . . . ? C3 C4 C5 N1 -0.8(6) . . . . ? C3 C4 C5 C6 177.3(4) . . . . ? N1 C5 C6 N2 -0.6(5) . . . . ? C4 C5 C6 N2 -178.9(4) . . . . ? N1 C5 C6 C7 177.6(4) . . . . ? C4 C5 C6 C7 -0.6(6) . . . . ? N2 C6 C7 C8 3.2(6) . . . . ? C5 C6 C7 C8 -175.0(4) . . . . ? C6 C7 C8 C9 -0.8(6) . . . . ? C7 C8 C9 C10 -1.8(6) . . . . ? C8 C9 C10 N2 2.4(6) . . . . ? C8 C9 C10 C11 -179.1(4) . . . . ? N2 C10 C11 N3 -8.6(6) . . . . ? C9 C10 C11 N3 172.8(4) . . . . ? N3 C12 C13 N4 -53.2(4) . . . . ? N4 C14 C15 N5 -6.7(6) . . . . ? N4 C14 C15 C16 173.6(4) . . . . ? N5 C15 C16 C17 1.7(7) . . . . ? C14 C15 C16 C17 -178.6(4) . . . . ? C15 C16 C17 C18 -2.2(7) . . . . ? C16 C17 C18 C19 0.4(7) . . . . ? C17 C18 C19 N5 2.0(7) . . . . ? C17 C18 C19 C20 -175.5(4) . . . . ? N5 C19 C20 N6 -2.0(5) . . . . ? C18 C19 C20 N6 175.7(4) . . . . ? N5 C19 C20 C21 -179.5(4) . . . . ? C18 C19 C20 C21 -1.8(7) . . . . ? N6 C20 C21 C22 -0.7(7) . . . . ? C19 C20 C21 C22 176.6(4) . . . . ? C20 C21 C22 C23 0.0(7) . . . . ? C21 C22 C23 C24 0.1(7) . . . . ? C22 C23 C24 N6 0.3(7) . . . . ? C2 C1 N1 C5 -2.0(6) . . . . ? C2 C1 N1 Eu1 167.0(3) . . . . ? C4 C5 N1 C1 2.7(6) . . . . ? C6 C5 N1 C1 -175.5(3) . . . . ? C4 C5 N1 Eu1 -166.3(3) . . . . ? C6 C5 N1 Eu1 15.5(4) . . . . ? O2 Eu1 N1 C1 44.9(3) . . . . ? O4 Eu1 N1 C1 -92.6(3) . . . . ? O5 Eu1 N1 C1 -123.1(3) . . . . ? O1 Eu1 N1 C1 97.6(3) . . . . ? N4 Eu1 N1 C1 66.7(4) . . . . ? N3 Eu1 N1 C1 161.3(3) . . . . ? N2 Eu1 N1 C1 175.4(3) . . . . ? N5 Eu1 N1 C1 -7.8(3) . . . . ? N6 Eu1 N1 C1 -52.8(3) . . . . ? O2 Eu1 N1 C5 -146.4(3) . . . . ? O4 Eu1 N1 C5 76.1(3) . . . . ? O5 Eu1 N1 C5 45.6(3) . . . . ? O1 Eu1 N1 C5 -93.7(3) . . . . ? N4 Eu1 N1 C5 -124.6(3) . . . . ? N3 Eu1 N1 C5 -30.0(3) . . . . ? N2 Eu1 N1 C5 -15.9(3) . . . . ? N5 Eu1 N1 C5 160.9(3) . . . . ? N6 Eu1 N1 C5 115.9(3) . . . . ? C7 C6 N2 C10 -2.6(6) . . . . ? C5 C6 N2 C10 175.6(3) . . . . ? C7 C6 N2 Eu1 166.8(3) . . . . ? C5 C6 N2 Eu1 -15.0(5) . . . . ? C9 C10 N2 C6 -0.2(6) . . . . ? C11 C10 N2 C6 -178.7(3) . . . . ? C9 C10 N2 Eu1 -170.0(3) . . . . ? C11 C10 N2 Eu1 11.5(4) . . . . ? O2 Eu1 N2 C6 68.0(3) . . . . ? O4 Eu1 N2 C6 -116.9(3) . . . . ? O5 Eu1 N2 C6 -91.6(3) . . . . ? O1 Eu1 N2 C6 100.9(3) . . . . ? N4 Eu1 N2 C6 158.3(3) . . . . ? N3 Eu1 N2 C6 -177.2(3) . . . . ? N6 Eu1 N2 C6 -33.3(3) . . . . ? N1 Eu1 N2 C6 16.0(3) . . . . ? O2 Eu1 N2 C10 -122.7(3) . . . . ? O4 Eu1 N2 C10 52.5(3) . . . . ? O5 Eu1 N2 C10 77.8(3) . . . . ? O1 Eu1 N2 C10 -89.7(3) . . . . ? N4 Eu1 N2 C10 -32.4(3) . . . . ? N3 Eu1 N2 C10 -7.8(3) . . . . ? N6 Eu1 N2 C10 136.0(3) . . . . ? N1 Eu1 N2 C10 -174.7(3) . . . . ? C10 C11 N3 C12 177.0(4) . . . . ? C10 C11 N3 Eu1 1.3(5) . . . . ? C13 C12 N3 C11 -133.7(4) . . . . ? C13 C12 N3 Eu1 42.2(4) . . . . ? O2 Eu1 N3 C11 105.4(3) . . . . ? O4 Eu1 N3 C11 -120.5(3) . . . . ? O5 Eu1 N3 C11 -67.7(3) . . . . ? O1 Eu1 N3 C11 81.8(3) . . . . ? N4 Eu1 N3 C11 160.7(4) . . . . ? N2 Eu1 N3 C11 3.2(3) . . . . ? N5 Eu1 N3 C11 -175.0(3) . . . . ? N6 Eu1 N3 C11 -87.8(4) . . . . ? N1 Eu1 N3 C11 17.0(4) . . . . ? O2 Eu1 N3 C12 -70.3(3) . . . . ? O4 Eu1 N3 C12 63.8(3) . . . . ? O5 Eu1 N3 C12 116.6(3) . . . . ? O1 Eu1 N3 C12 -93.9(3) . . . . ? N4 Eu1 N3 C12 -15.0(3) . . . . ? N2 Eu1 N3 C12 -172.5(3) . . . . ? N5 Eu1 N3 C12 9.3(3) . . . . ? N6 Eu1 N3 C12 96.5(3) . . . . ? N1 Eu1 N3 C12 -158.7(3) . . . . ? C15 C14 N4 C13 177.4(4) . . . . ? C15 C14 N4 Eu1 -0.1(6) . . . . ? C12 C13 N4 C14 -134.0(4) . . . . ? C12 C13 N4 Eu1 43.6(4) . . . . ? O2 Eu1 N4 C14 -64.9(3) . . . . ? O4 Eu1 N4 C14 79.3(3) . . . . ? O5 Eu1 N4 C14 105.0(3) . . . . ? O1 Eu1 N4 C14 -117.7(4) . . . . ? N3 Eu1 N4 C14 160.9(4) . . . . ? N2 Eu1 N4 C14 -174.9(3) . . . . ? N5 Eu1 N4 C14 3.6(3) . . . . ? N6 Eu1 N4 C14 17.9(4) . . . . ? N1 Eu1 N4 C14 -86.2(4) . . . . ? O2 Eu1 N4 C13 117.5(3) . . . . ? O4 Eu1 N4 C13 -98.2(3) . . . . ? O5 Eu1 N4 C13 -72.5(3) . . . . ? O1 Eu1 N4 C13 64.8(3) . . . . ? N3 Eu1 N4 C13 -16.7(3) . . . . ? N2 Eu1 N4 C13 7.6(3) . . . . ? N5 Eu1 N4 C13 -173.9(3) . . . . ? N6 Eu1 N4 C13 -159.7(3) . . . . ? N1 Eu1 N4 C13 96.3(3) . . . . ? C18 C19 N5 C15 -2.5(6) . . . . ? C20 C19 N5 C15 175.2(4) . . . . ? C18 C19 N5 Eu1 168.2(3) . . . . ? C20 C19 N5 Eu1 -14.1(5) . . . . ? C16 C15 N5 C19 0.7(6) . . . . ? C14 C15 N5 C19 -179.0(4) . . . . ? C16 C15 N5 Eu1 -170.5(3) . . . . ? C14 C15 N5 Eu1 9.9(5) . . . . ? O2 Eu1 N5 C19 -89.7(3) . . . . ? O4 Eu1 N5 C19 100.5(3) . . . . ? O5 Eu1 N5 C19 70.0(3) . . . . ? O1 Eu1 N5 C19 -117.7(3) . . . . ? N4 Eu1 N5 C19 -177.8(3) . . . . ? N3 Eu1 N5 C19 157.4(3) . . . . ? N6 Eu1 N5 C19 15.8(3) . . . . ? N1 Eu1 N5 C19 -33.4(3) . . . . ? O2 Eu1 N5 C15 81.0(3) . . . . ? O4 Eu1 N5 C15 -88.7(3) . . . . ? O5 Eu1 N5 C15 -119.3(3) . . . . ? O1 Eu1 N5 C15 53.0(3) . . . . ? N4 Eu1 N5 C15 -7.1(3) . . . . ? N3 Eu1 N5 C15 -31.8(3) . . . . ? N6 Eu1 N5 C15 -173.4(3) . . . . ? N1 Eu1 N5 C15 137.3(3) . . . . ? C23 C24 N6 C20 -1.0(6) . . . . ? C23 C24 N6 Eu1 165.9(3) . . . . ? C21 C20 N6 C24 1.1(6) . . . . ? C19 C20 N6 C24 -176.3(4) . . . . ? C21 C20 N6 Eu1 -165.5(3) . . . . ? C19 C20 N6 Eu1 17.0(5) . . . . ? O2 Eu1 N6 C24 -122.0(3) . . . . ? O4 Eu1 N6 C24 102.0(3) . . . . ? O5 Eu1 N6 C24 48.8(3) . . . . ? O1 Eu1 N6 C24 -96.0(3) . . . . ? N4 Eu1 N6 C24 162.4(3) . . . . ? N3 Eu1 N6 C24 69.3(4) . . . . ? N2 Eu1 N6 C24 -6.2(3) . . . . ? N5 Eu1 N6 C24 176.9(3) . . . . ? N1 Eu1 N6 C24 -51.4(3) . . . . ? O2 Eu1 N6 C20 44.5(3) . . . . ? O4 Eu1 N6 C20 -91.6(3) . . . . ? O5 Eu1 N6 C20 -144.7(3) . . . . ? O1 Eu1 N6 C20 70.5(3) . . . . ? N4 Eu1 N6 C20 -31.2(3) . . . . ? N3 Eu1 N6 C20 -124.3(3) . . . . ? N2 Eu1 N6 C20 160.3(3) . . . . ? N5 Eu1 N6 C20 -16.7(3) . . . . ? N1 Eu1 N6 C20 115.1(3) . . . . ? O3 N7 O1 Eu1 176.2(3) . . . . ? O2 N7 O1 Eu1 -3.6(3) . . . . ? O2 Eu1 O1 N7 2.13(19) . . . . ? O4 Eu1 O1 N7 117.4(2) . . . . ? O5 Eu1 O1 N7 -155.5(2) . . . . ? N4 Eu1 O1 N7 88.8(2) . . . . ? N3 Eu1 O1 N7 156.1(2) . . . . ? N2 Eu1 O1 N7 -138.0(2) . . . . ? N5 Eu1 O1 N7 35.4(2) . . . . ? N6 Eu1 O1 N7 -32.1(3) . . . . ? N1 Eu1 O1 N7 -74.5(2) . . . . ? O3 N7 O2 Eu1 -176.1(3) . . . . ? O1 N7 O2 Eu1 3.7(3) . . . . ? O4 Eu1 O2 N7 -133.7(2) . . . . ? O5 Eu1 O2 N7 126.8(3) . . . . ? O1 Eu1 O2 N7 -2.1(2) . . . . ? N4 Eu1 O2 N7 -81.6(2) . . . . ? N3 Eu1 O2 N7 -32.1(3) . . . . ? N2 Eu1 O2 N7 39.9(2) . . . . ? N5 Eu1 O2 N7 -147.3(2) . . . . ? N6 Eu1 O2 N7 155.1(2) . . . . ? N1 Eu1 O2 N7 86.6(2) . . . . ? O6 N8 O4 Eu1 170.9(3) . . . . ? O5 N8 O4 Eu1 -7.5(3) . . . . ? O2 Eu1 O4 N8 -151.5(2) . . . . ? O5 Eu1 O4 N8 4.37(19) . . . . ? O1 Eu1 O4 N8 126.6(2) . . . . ? N4 Eu1 O4 N8 155.1(2) . . . . ? N3 Eu1 O4 N8 87.9(2) . . . . ? N2 Eu1 O4 N8 34.7(2) . . . . ? N5 Eu1 O4 N8 -138.4(2) . . . . ? N6 Eu1 O4 N8 -74.5(2) . . . . ? N1 Eu1 O4 N8 -36.3(3) . . . . ? O6 N8 O5 Eu1 -170.9(3) . . . . ? O4 N8 O5 Eu1 7.5(3) . . . . ? O2 Eu1 O5 N8 111.3(3) . . . . ? O4 Eu1 O5 N8 -4.4(2) . . . . ? O1 Eu1 O5 N8 -135.4(2) . . . . ? N4 Eu1 O5 N8 -36.8(2) . . . . ? N3 Eu1 O5 N8 -87.1(2) . . . . ? N2 Eu1 O5 N8 -153.7(2) . . . . ? N5 Eu1 O5 N8 33.5(2) . . . . ? N6 Eu1 O5 N8 81.6(2) . . . . ? N1 Eu1 O5 N8 149.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 2.639 _refine_diff_density_min -1.439 _refine_diff_density_rms 0.140 _database_code_depnum_ccdc_archive 'CCDC 919427' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Gd_enbpy2_NO3_PF6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H23 F6 Gd N9 O6 P' _chemical_formula_weight 859.75 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 9.0151(7) _cell_length_b 12.2140(9) _cell_length_c 16.1835(12) _cell_angle_alpha 112.0360(10) _cell_angle_beta 104.2970(10) _cell_angle_gamma 91.8260(10) _cell_volume 1585.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 8564 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.40 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.801 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 846 _exptl_absorpt_coefficient_mu 2.234 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6893 _exptl_absorpt_correction_T_max 0.8075 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 17967 _diffrn_reflns_av_R_equivalents 0.0272 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 27.56 _reflns_number_total 7105 _reflns_number_gt 6505 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ISOR restraints for F1, F2, and F6 atoms of the PF6 anion were used in order to address non-positive-definite errors. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+3.4490P] 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 7105 _refine_ls_number_parameters 443 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0821 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.108 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5188(4) 0.5705(3) 0.2562(3) 0.0208(8) Uani 1 1 d . A 6 H1 H 0.5028 0.5248 0.2903 0.025 Uiso 1 1 calc R A 6 C2 C 0.4569(5) 0.6759(4) 0.2726(3) 0.0241(8) Uani 1 1 d . A 6 H2 H 0.3986 0.7013 0.3163 0.029 Uiso 1 1 calc R A 6 C3 C 0.4814(5) 0.7436(4) 0.2244(3) 0.0269(9) Uani 1 1 d . A 6 H3 H 0.4432 0.8179 0.2358 0.032 Uiso 1 1 calc R A 6 C4 C 0.5624(4) 0.7018(4) 0.1592(3) 0.0228(8) Uani 1 1 d . A 6 H4 H 0.5789 0.7464 0.1244 0.027 Uiso 1 1 calc R A 6 C5 C 0.6198(4) 0.5937(3) 0.1448(3) 0.0178(7) Uani 1 1 d . A 6 C6 C 0.7007(4) 0.5404(3) 0.0724(3) 0.0181(7) Uani 1 1 d . A 6 C7 C 0.7248(4) 0.5949(4) 0.0143(3) 0.0229(8) Uani 1 1 d . A 6 H7 H 0.6966 0.6720 0.0232 0.028 Uiso 1 1 calc R A 6 C8 C 0.7902(4) 0.5358(4) -0.0567(3) 0.0240(8) Uani 1 1 d . A 6 H8 H 0.8062 0.5712 -0.0975 0.029 Uiso 1 1 calc R A 6 C9 C 0.8318(4) 0.4245(4) -0.0667(3) 0.0240(8) Uani 1 1 d . A 6 H9 H 0.8744 0.3811 -0.1156 0.029 Uiso 1 1 calc R A 6 C10 C 0.8100(4) 0.3775(4) -0.0043(2) 0.0201(8) Uani 1 1 d . A 6 C11 C 0.8540(4) 0.2604(4) -0.0099(3) 0.0216(8) Uani 1 1 d . A 6 H11 H 0.8870 0.2107 -0.0613 0.026 Uiso 1 1 calc R A 6 C12 C 0.8824(5) 0.1067(3) 0.0452(3) 0.0250(8) Uani 1 1 d . A 6 H12A H 0.9854 0.1119 0.0873 0.030 Uiso 1 1 calc R A 6 H12B H 0.8829 0.0581 -0.0193 0.030 Uiso 1 1 calc R A 6 C13 C 0.7575(5) 0.0501(4) 0.0712(3) 0.0262(9) Uani 1 1 d . A 6 H13A H 0.6566 0.0349 0.0243 0.031 Uiso 1 1 calc R A 6 H13B H 0.7837 -0.0268 0.0740 0.031 Uiso 1 1 calc R A 6 C14 C 0.7449(5) 0.0942(4) 0.2237(3) 0.0243(8) Uani 1 1 d . A 6 H14 H 0.7425 0.0113 0.2101 0.029 Uiso 1 1 calc R A 6 C15 C 0.7431(4) 0.1782(4) 0.3166(3) 0.0225(8) Uani 1 1 d . A 6 C16 C 0.7234(5) 0.1381(4) 0.3836(3) 0.0305(9) Uani 1 1 d . A 6 H16 H 0.7121 0.0555 0.3713 0.037 Uiso 1 1 calc R A 6 C17 C 0.7208(6) 0.2228(4) 0.4688(3) 0.0335(10) Uani 1 1 d . A 6 H17 H 0.7052 0.1987 0.5158 0.040 Uiso 1 1 calc R A 6 C18 C 0.7410(5) 0.3415(4) 0.4850(3) 0.0290(9) Uani 1 1 d . A 6 H18 H 0.7381 0.4002 0.5429 0.035 Uiso 1 1 calc R A 6 C19 C 0.7660(4) 0.3758(4) 0.4155(3) 0.0218(8) Uani 1 1 d . A 6 C20 C 0.8025(4) 0.5020(4) 0.4301(3) 0.0212(8) Uani 1 1 d . A 6 C21 C 0.8114(5) 0.5968(4) 0.5135(3) 0.0281(9) Uani 1 1 d . A 6 H21 H 0.7883 0.5824 0.5631 0.034 Uiso 1 1 calc R A 6 C22 C 0.8539(5) 0.7114(4) 0.5238(3) 0.0338(10) Uani 1 1 d . A 6 H22 H 0.8607 0.7768 0.5804 0.041 Uiso 1 1 calc R A 6 C23 C 0.8866(5) 0.7303(4) 0.4510(3) 0.0286(9) Uani 1 1 d . A 6 H23 H 0.9164 0.8086 0.4567 0.034 Uiso 1 1 calc R A 6 C24 C 0.8751(4) 0.6330(3) 0.3697(3) 0.0222(8) Uani 1 1 d . A 6 H24 H 0.8980 0.6462 0.3197 0.027 Uiso 1 1 calc R A 6 C25 C 0.3643(5) 0.0537(4) 0.2085(3) 0.0271(9) Uani 1 1 d . B 6 C26 C 0.3100(6) 0.1467(4) 0.2777(4) 0.0382(11) Uani 1 1 d . B 6 H26A H 0.3320 0.1330 0.3352 0.057 Uiso 1 1 calc R B 6 H26B H 0.1983 0.1445 0.2541 0.057 Uiso 1 1 calc R B 6 H26C H 0.3632 0.2248 0.2901 0.057 Uiso 1 1 calc R B 6 F1 F 0.0143(6) 0.7365(4) 0.2361(4) 0.1013(16) Uani 1 1 d U C 6 F2 F 0.1022(5) 0.8752(5) 0.3796(3) 0.1010(16) Uani 1 1 d U C 6 F3 F 0.0408(4) 1.0183(3) 0.3220(3) 0.0601(10) Uani 1 1 d . C 6 F4 F -0.0422(7) 0.8772(5) 0.1822(3) 0.1031(17) Uani 1 1 d . C 6 F5 F -0.1328(4) 0.8678(3) 0.2960(2) 0.0526(8) Uani 1 1 d . C 6 F6 F 0.1979(5) 0.8867(4) 0.2663(4) 0.0845(14) Uani 1 1 d U C 6 Gd1 Gd 0.75723(2) 0.351637(15) 0.191521(12) 0.01509(6) Uani 1 1 d . A 6 N1 N 0.6008(4) 0.5292(3) 0.1945(2) 0.0175(6) Uani 1 1 d . A 6 N2 N 0.7458(3) 0.4343(3) 0.0647(2) 0.0173(6) Uani 1 1 d . A 6 N3 N 0.8475(4) 0.2264(3) 0.0540(2) 0.0208(7) Uani 1 1 d . A 6 N4 N 0.7497(4) 0.1336(3) 0.1620(2) 0.0210(7) Uani 1 1 d . A 6 N5 N 0.7638(4) 0.2943(3) 0.3317(2) 0.0195(6) Uani 1 1 d . A 6 N6 N 0.8331(4) 0.5206(3) 0.3580(2) 0.0193(6) Uani 1 1 d . A 6 N7 N 0.4289(4) 0.2555(3) 0.1199(2) 0.0190(6) Uani 1 1 d . A 6 N8 N 1.0923(4) 0.4153(3) 0.2565(2) 0.0208(7) Uani 1 1 d . A 6 N9 N 0.4077(5) -0.0190(3) 0.1556(3) 0.0340(9) Uani 1 1 d . B 6 O1 O 0.5119(3) 0.2484(2) 0.06531(18) 0.0226(6) Uani 1 1 d . A 6 O2 O 0.4998(3) 0.3010(2) 0.20650(18) 0.0202(5) Uani 1 1 d . A 6 O3 O 0.2902(3) 0.2211(3) 0.0914(2) 0.0262(6) Uani 1 1 d . A 6 O4 O 1.0256(3) 0.3257(2) 0.26155(18) 0.0218(6) Uani 1 1 d . A 6 O5 O 1.0069(3) 0.4685(2) 0.21249(18) 0.0218(6) Uani 1 1 d . A 6 O6 O 1.2310(3) 0.4501(3) 0.2933(2) 0.0287(6) Uani 1 1 d . A 6 P1 P 0.03612(17) 0.87979(11) 0.28453(10) 0.0386(3) Uani 1 1 d . C 6 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 C1 0.0213(19) 0.0241(19) 0.0180(18) 0.0086(15) 0.0069(15) 0.0047(15) C2 0.023(2) 0.027(2) 0.0213(19) 0.0068(16) 0.0083(16) 0.0067(16) C3 0.024(2) 0.022(2) 0.031(2) 0.0079(17) 0.0055(17) 0.0076(16) C4 0.0196(19) 0.0229(19) 0.027(2) 0.0132(16) 0.0026(16) 0.0031(15) C5 0.0139(17) 0.0203(18) 0.0166(17) 0.0064(14) 0.0015(14) 0.0007(14) C6 0.0132(16) 0.0229(19) 0.0163(17) 0.0078(15) 0.0011(14) -0.0003(14) C7 0.0184(18) 0.029(2) 0.025(2) 0.0162(17) 0.0038(15) 0.0030(16) C8 0.0173(18) 0.039(2) 0.0191(19) 0.0178(17) 0.0020(15) -0.0017(16) C9 0.0170(18) 0.036(2) 0.0176(18) 0.0099(17) 0.0038(15) 0.0018(16) C10 0.0167(17) 0.026(2) 0.0128(17) 0.0047(15) 0.0015(14) 0.0010(15) C11 0.0185(18) 0.026(2) 0.0163(18) 0.0032(15) 0.0061(15) 0.0052(15) C12 0.029(2) 0.022(2) 0.0202(19) 0.0051(16) 0.0055(16) 0.0116(16) C13 0.035(2) 0.0179(18) 0.0205(19) 0.0039(15) 0.0037(17) 0.0062(16) C14 0.023(2) 0.0222(19) 0.027(2) 0.0111(16) 0.0038(16) 0.0039(16) C15 0.0184(18) 0.027(2) 0.024(2) 0.0144(17) 0.0020(15) 0.0032(15) C16 0.033(2) 0.033(2) 0.029(2) 0.0180(19) 0.0064(18) 0.0020(18) C17 0.039(3) 0.042(3) 0.026(2) 0.020(2) 0.0099(19) 0.004(2) C18 0.033(2) 0.038(2) 0.0187(19) 0.0139(18) 0.0084(17) 0.0047(19) C19 0.0194(18) 0.028(2) 0.0179(18) 0.0102(16) 0.0038(15) 0.0025(15) C20 0.0184(18) 0.027(2) 0.0163(18) 0.0065(15) 0.0048(14) 0.0023(15) C21 0.030(2) 0.034(2) 0.0174(19) 0.0062(17) 0.0081(17) -0.0008(18) C22 0.039(3) 0.033(2) 0.018(2) -0.0048(17) 0.0131(19) -0.0017(19) C23 0.025(2) 0.025(2) 0.028(2) 0.0019(17) 0.0094(17) -0.0028(17) C24 0.0228(19) 0.0244(19) 0.0183(18) 0.0061(15) 0.0077(15) 0.0027(15) C25 0.025(2) 0.031(2) 0.028(2) 0.0174(19) 0.0061(17) 0.0005(17) C26 0.045(3) 0.036(3) 0.049(3) 0.023(2) 0.029(2) 0.012(2) F1 0.137(4) 0.046(2) 0.151(4) 0.033(2) 0.101(3) 0.031(2) F2 0.065(2) 0.180(4) 0.096(3) 0.103(3) 0.008(2) 0.019(3) F3 0.0495(19) 0.0245(15) 0.104(3) 0.0151(16) 0.0346(19) 0.0033(13) F4 0.153(5) 0.118(4) 0.050(2) 0.035(3) 0.045(3) 0.039(4) F5 0.0480(18) 0.0413(17) 0.069(2) 0.0199(16) 0.0206(16) 0.0002(14) F6 0.078(3) 0.080(3) 0.160(4) 0.084(3) 0.084(3) 0.046(2) Gd1 0.01679(10) 0.01624(10) 0.01245(9) 0.00549(7) 0.00456(7) 0.00355(6) N1 0.0181(15) 0.0181(15) 0.0174(15) 0.0078(12) 0.0057(12) 0.0025(12) N2 0.0165(15) 0.0210(16) 0.0142(14) 0.0074(12) 0.0032(12) 0.0025(12) N3 0.0195(16) 0.0218(16) 0.0176(15) 0.0047(13) 0.0037(13) 0.0055(13) N4 0.0216(16) 0.0192(16) 0.0197(16) 0.0062(13) 0.0036(13) 0.0039(13) N5 0.0187(15) 0.0235(16) 0.0169(15) 0.0091(13) 0.0042(12) 0.0027(13) N6 0.0191(15) 0.0227(16) 0.0160(15) 0.0072(13) 0.0054(12) 0.0050(13) N7 0.0207(16) 0.0143(15) 0.0209(16) 0.0072(12) 0.0035(13) 0.0018(12) N8 0.0188(16) 0.0283(17) 0.0152(15) 0.0068(13) 0.0075(13) 0.0023(13) N9 0.038(2) 0.032(2) 0.029(2) 0.0102(17) 0.0080(17) 0.0015(17) O1 0.0235(14) 0.0265(14) 0.0193(13) 0.0097(11) 0.0070(11) 0.0052(11) O2 0.0224(13) 0.0211(13) 0.0172(13) 0.0078(11) 0.0057(11) 0.0018(11) O3 0.0193(14) 0.0259(15) 0.0300(15) 0.0108(12) 0.0018(12) -0.0028(11) O4 0.0204(13) 0.0259(14) 0.0205(13) 0.0106(11) 0.0061(11) 0.0031(11) O5 0.0231(14) 0.0247(14) 0.0195(13) 0.0102(11) 0.0068(11) 0.0040(11) O6 0.0174(14) 0.0410(18) 0.0256(15) 0.0112(13) 0.0059(12) -0.0007(12) P1 0.0544(8) 0.0286(6) 0.0554(8) 0.0256(6) 0.0382(7) 0.0209(6) _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 C1 N1 1.345(5) . ? C1 C2 1.378(5) . ? C1 H1 0.9500 . ? C2 C3 1.378(6) . ? C2 H2 0.9500 . ? C3 C4 1.381(6) . ? C3 H3 0.9500 . ? C4 C5 1.391(5) . ? C4 H4 0.9500 . ? C5 N1 1.353(5) . ? C5 C6 1.487(5) . ? C6 N2 1.340(5) . ? C6 C7 1.391(5) . ? C7 C8 1.389(6) . ? C7 H7 0.9500 . ? C8 C9 1.383(6) . ? C8 H8 0.9500 . ? C9 C10 1.384(5) . ? C9 H9 0.9500 . ? C10 N2 1.352(5) . ? C10 C11 1.472(6) . ? C11 N3 1.263(5) . ? C11 H11 0.9500 . ? C12 N3 1.467(5) . ? C12 C13 1.525(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.462(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.268(5) . ? C14 C15 1.472(6) . ? C14 H14 0.9500 . ? C15 N5 1.344(5) . ? C15 C16 1.390(6) . ? C16 C17 1.386(7) . ? C16 H16 0.9500 . ? C17 C18 1.371(6) . ? C17 H17 0.9500 . ? C18 C19 1.402(5) . ? C18 H18 0.9500 . ? C19 N5 1.342(5) . ? C19 C20 1.482(6) . ? C20 N6 1.358(5) . ? C20 C21 1.392(5) . ? C21 C22 1.377(6) . ? C21 H21 0.9500 . ? C22 C23 1.376(6) . ? C22 H22 0.9500 . ? C23 C24 1.381(5) . ? C23 H23 0.9500 . ? C24 N6 1.341(5) . ? C24 H24 0.9500 . ? C25 N9 1.136(6) . ? C25 C26 1.461(6) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? F1 P1 1.609(4) . ? F2 P1 1.530(4) . ? F3 P1 1.563(3) . ? F4 P1 1.620(5) . ? F5 P1 1.587(3) . ? F6 P1 1.563(4) . ? Gd1 O2 2.475(3) . ? Gd1 O4 2.490(3) . ? Gd1 O5 2.505(3) . ? Gd1 O1 2.512(3) . ? Gd1 N4 2.519(3) . ? Gd1 N3 2.525(3) . ? Gd1 N2 2.588(3) . ? Gd1 N5 2.602(3) . ? Gd1 N6 2.610(3) . ? Gd1 N1 2.617(3) . ? N7 O3 1.220(4) . ? N7 O1 1.273(4) . ? N7 O2 1.277(4) . ? N8 O6 1.227(4) . ? N8 O4 1.272(4) . ? N8 O5 1.276(4) . ? 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 N1 C1 C2 123.3(4) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C3 C2 C1 118.7(4) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 119.0(4) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 119.5(4) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 121.6(3) . . ? N1 C5 C6 116.0(3) . . ? C4 C5 C6 122.4(3) . . ? N2 C6 C7 121.8(4) . . ? N2 C6 C5 115.7(3) . . ? C7 C6 C5 122.4(3) . . ? C8 C7 C6 119.4(4) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C9 C8 C7 118.8(4) . . ? C9 C8 H8 120.6 . . ? C7 C8 H8 120.6 . . ? C8 C9 C10 118.7(4) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? N2 C10 C9 122.8(4) . . ? N2 C10 C11 115.5(3) . . ? C9 C10 C11 121.7(3) . . ? N3 C11 C10 119.6(3) . . ? N3 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? N3 C12 C13 107.5(3) . . ? N3 C12 H12A 110.2 . . ? C13 C12 H12A 110.2 . . ? N3 C12 H12B 110.2 . . ? C13 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? N4 C13 C12 107.3(3) . . ? N4 C13 H13A 110.3 . . ? C12 C13 H13A 110.3 . . ? N4 C13 H13B 110.3 . . ? C12 C13 H13B 110.3 . . ? H13A C13 H13B 108.5 . . ? N4 C14 C15 119.4(4) . . ? N4 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? N5 C15 C16 123.2(4) . . ? N5 C15 C14 115.5(3) . . ? C16 C15 C14 121.4(4) . . ? C17 C16 C15 117.8(4) . . ? C17 C16 H16 121.1 . . ? C15 C16 H16 121.1 . . ? C18 C17 C16 119.6(4) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 119.6(4) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? N5 C19 C18 121.2(4) . . ? N5 C19 C20 115.9(3) . . ? C18 C19 C20 122.9(4) . . ? N6 C20 C21 121.2(4) . . ? N6 C20 C19 116.0(3) . . ? C21 C20 C19 122.8(4) . . ? C22 C21 C20 119.6(4) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C23 C22 C21 119.3(4) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C22 C23 C24 118.7(4) . . ? C22 C23 H23 120.7 . . ? C24 C23 H23 120.7 . . ? N6 C24 C23 123.1(4) . . ? N6 C24 H24 118.5 . . ? C23 C24 H24 118.5 . . ? N9 C25 C26 179.0(5) . . ? O2 Gd1 O4 134.54(9) . . ? O2 Gd1 O5 161.12(9) . . ? O4 Gd1 O5 51.40(9) . . ? O2 Gd1 O1 51.35(9) . . ? O4 Gd1 O1 143.96(9) . . ? O5 Gd1 O1 138.39(9) . . ? O2 Gd1 N4 77.46(10) . . ? O4 Gd1 N4 74.06(10) . . ? O5 Gd1 N4 118.98(10) . . ? O1 Gd1 N4 74.13(10) . . ? O2 Gd1 N3 121.68(10) . . ? O4 Gd1 N3 75.77(9) . . ? O5 Gd1 N3 76.07(10) . . ? O1 Gd1 N3 75.69(9) . . ? N4 Gd1 N3 64.82(11) . . ? O2 Gd1 N2 113.45(9) . . ? O4 Gd1 N2 111.78(9) . . ? O5 Gd1 N2 66.69(9) . . ? O1 Gd1 N2 73.54(9) . . ? N4 Gd1 N2 123.80(10) . . ? N3 Gd1 N2 63.37(10) . . ? O2 Gd1 N5 65.40(9) . . ? O4 Gd1 N5 70.27(9) . . ? O5 Gd1 N5 111.99(9) . . ? O1 Gd1 N5 108.96(9) . . ? N4 Gd1 N5 63.05(10) . . ? N3 Gd1 N5 123.38(10) . . ? N2 Gd1 N5 173.03(10) . . ? O2 Gd1 N6 90.92(9) . . ? O4 Gd1 N6 76.26(9) . . ? O5 Gd1 N6 72.55(9) . . ? O1 Gd1 N6 136.69(9) . . ? N4 Gd1 N6 122.98(10) . . ? N3 Gd1 N6 146.76(10) . . ? N2 Gd1 N6 112.14(10) . . ? N5 Gd1 N6 61.45(10) . . ? O2 Gd1 N1 72.00(9) . . ? O4 Gd1 N1 137.14(9) . . ? O5 Gd1 N1 93.18(9) . . ? O1 Gd1 N1 77.86(9) . . ? N4 Gd1 N1 147.33(10) . . ? N3 Gd1 N1 123.47(10) . . ? N2 Gd1 N1 61.53(10) . . ? N5 Gd1 N1 112.23(10) . . ? N6 Gd1 N1 69.54(10) . . ? C1 N1 C5 117.8(3) . . ? C1 N1 Gd1 120.6(2) . . ? C5 N1 Gd1 120.7(2) . . ? C6 N2 C10 118.4(3) . . ? C6 N2 Gd1 122.4(2) . . ? C10 N2 Gd1 118.4(2) . . ? C11 N3 C12 119.2(3) . . ? C11 N3 Gd1 122.2(3) . . ? C12 N3 Gd1 118.4(2) . . ? C14 N4 C13 118.9(3) . . ? C14 N4 Gd1 122.7(3) . . ? C13 N4 Gd1 118.3(2) . . ? C19 N5 C15 118.6(3) . . ? C19 N5 Gd1 122.1(2) . . ? C15 N5 Gd1 118.7(2) . . ? C24 N6 C20 118.2(3) . . ? C24 N6 Gd1 119.6(2) . . ? C20 N6 Gd1 120.9(2) . . ? O3 N7 O1 122.2(3) . . ? O3 N7 O2 122.0(3) . . ? O1 N7 O2 115.8(3) . . ? O6 N8 O4 121.8(3) . . ? O6 N8 O5 121.8(3) . . ? O4 N8 O5 116.4(3) . . ? N7 O1 Gd1 95.5(2) . . ? N7 O2 Gd1 97.2(2) . . ? N8 O4 Gd1 96.2(2) . . ? N8 O5 Gd1 95.4(2) . . ? F2 P1 F6 93.7(3) . . ? F2 P1 F3 95.7(3) . . ? F6 P1 F3 92.4(2) . . ? F2 P1 F5 89.4(2) . . ? F6 P1 F5 176.3(3) . . ? F3 P1 F5 89.42(17) . . ? F2 P1 F1 90.2(3) . . ? F6 P1 F1 90.5(2) . . ? F3 P1 F1 173.3(3) . . ? F5 P1 F1 87.3(2) . . ? F2 P1 F4 176.2(3) . . ? F6 P1 F4 88.8(3) . . ? F3 P1 F4 87.0(2) . . ? F5 P1 F4 88.0(3) . . ? F1 P1 F4 86.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.8(6) . . . . ? C1 C2 C3 C4 2.2(6) . . . . ? C2 C3 C4 C5 -1.2(6) . . . . ? C3 C4 C5 N1 -1.3(6) . . . . ? C3 C4 C5 C6 176.7(4) . . . . ? N1 C5 C6 N2 -0.1(5) . . . . ? C4 C5 C6 N2 -178.2(3) . . . . ? N1 C5 C6 C7 178.2(3) . . . . ? C4 C5 C6 C7 0.1(6) . . . . ? N2 C6 C7 C8 3.3(6) . . . . ? C5 C6 C7 C8 -174.9(3) . . . . ? C6 C7 C8 C9 -0.9(6) . . . . ? C7 C8 C9 C10 -1.6(6) . . . . ? C8 C9 C10 N2 1.9(6) . . . . ? C8 C9 C10 C11 -179.0(3) . . . . ? N2 C10 C11 N3 -8.3(5) . . . . ? C9 C10 C11 N3 172.5(4) . . . . ? N3 C12 C13 N4 -52.7(4) . . . . ? N4 C14 C15 N5 -7.0(5) . . . . ? N4 C14 C15 C16 173.9(4) . . . . ? N5 C15 C16 C17 1.9(6) . . . . ? C14 C15 C16 C17 -179.1(4) . . . . ? C15 C16 C17 C18 -1.5(7) . . . . ? C16 C17 C18 C19 -0.8(7) . . . . ? C17 C18 C19 N5 2.9(6) . . . . ? C17 C18 C19 C20 -174.4(4) . . . . ? N5 C19 C20 N6 -1.5(5) . . . . ? C18 C19 C20 N6 176.0(4) . . . . ? N5 C19 C20 C21 -179.0(4) . . . . ? C18 C19 C20 C21 -1.5(6) . . . . ? N6 C20 C21 C22 -0.8(6) . . . . ? C19 C20 C21 C22 176.6(4) . . . . ? C20 C21 C22 C23 0.2(7) . . . . ? C21 C22 C23 C24 0.1(7) . . . . ? C22 C23 C24 N6 0.2(6) . . . . ? C2 C1 N1 C5 -1.5(6) . . . . ? C2 C1 N1 Gd1 168.1(3) . . . . ? C4 C5 N1 C1 2.6(5) . . . . ? C6 C5 N1 C1 -175.5(3) . . . . ? C4 C5 N1 Gd1 -167.0(3) . . . . ? C6 C5 N1 Gd1 14.8(4) . . . . ? O2 Gd1 N1 C1 44.4(3) . . . . ? O4 Gd1 N1 C1 -92.8(3) . . . . ? O5 Gd1 N1 C1 -123.7(3) . . . . ? O1 Gd1 N1 C1 97.4(3) . . . . ? N4 Gd1 N1 C1 66.0(3) . . . . ? N3 Gd1 N1 C1 161.0(3) . . . . ? N2 Gd1 N1 C1 175.1(3) . . . . ? N5 Gd1 N1 C1 -8.3(3) . . . . ? N6 Gd1 N1 C1 -53.6(3) . . . . ? O2 Gd1 N1 C5 -146.3(3) . . . . ? O4 Gd1 N1 C5 76.5(3) . . . . ? O5 Gd1 N1 C5 45.7(3) . . . . ? O1 Gd1 N1 C5 -93.3(3) . . . . ? N4 Gd1 N1 C5 -124.6(3) . . . . ? N3 Gd1 N1 C5 -29.7(3) . . . . ? N2 Gd1 N1 C5 -15.6(2) . . . . ? N5 Gd1 N1 C5 161.0(3) . . . . ? N6 Gd1 N1 C5 115.7(3) . . . . ? C7 C6 N2 C10 -3.0(5) . . . . ? C5 C6 N2 C10 175.3(3) . . . . ? C7 C6 N2 Gd1 166.5(3) . . . . ? C5 C6 N2 Gd1 -15.2(4) . . . . ? C9 C10 N2 C6 0.4(5) . . . . ? C11 C10 N2 C6 -178.8(3) . . . . ? C9 C10 N2 Gd1 -169.5(3) . . . . ? C11 C10 N2 Gd1 11.2(4) . . . . ? O2 Gd1 N2 C6 67.7(3) . . . . ? O4 Gd1 N2 C6 -117.0(3) . . . . ? O5 Gd1 N2 C6 -91.7(3) . . . . ? O1 Gd1 N2 C6 100.8(3) . . . . ? N4 Gd1 N2 C6 158.0(3) . . . . ? N3 Gd1 N2 C6 -177.3(3) . . . . ? N6 Gd1 N2 C6 -33.6(3) . . . . ? N1 Gd1 N2 C6 15.9(3) . . . . ? O2 Gd1 N2 C10 -122.8(3) . . . . ? O4 Gd1 N2 C10 52.5(3) . . . . ? O5 Gd1 N2 C10 77.8(3) . . . . ? O1 Gd1 N2 C10 -89.7(3) . . . . ? N4 Gd1 N2 C10 -32.4(3) . . . . ? N3 Gd1 N2 C10 -7.7(2) . . . . ? N6 Gd1 N2 C10 136.0(3) . . . . ? N1 Gd1 N2 C10 -174.6(3) . . . . ? C10 C11 N3 C12 176.3(3) . . . . ? C10 C11 N3 Gd1 1.0(5) . . . . ? C13 C12 N3 C11 -134.1(4) . . . . ? C13 C12 N3 Gd1 41.5(4) . . . . ? O2 Gd1 N3 C11 105.7(3) . . . . ? O4 Gd1 N3 C11 -120.4(3) . . . . ? O5 Gd1 N3 C11 -67.3(3) . . . . ? O1 Gd1 N3 C11 81.9(3) . . . . ? N4 Gd1 N3 C11 160.8(3) . . . . ? N2 Gd1 N3 C11 3.4(3) . . . . ? N5 Gd1 N3 C11 -174.6(3) . . . . ? N6 Gd1 N3 C11 -86.9(3) . . . . ? N1 Gd1 N3 C11 17.3(3) . . . . ? O2 Gd1 N3 C12 -69.7(3) . . . . ? O4 Gd1 N3 C12 64.2(3) . . . . ? O5 Gd1 N3 C12 117.4(3) . . . . ? O1 Gd1 N3 C12 -93.5(3) . . . . ? N4 Gd1 N3 C12 -14.6(3) . . . . ? N2 Gd1 N3 C12 -172.0(3) . . . . ? N5 Gd1 N3 C12 10.0(3) . . . . ? N6 Gd1 N3 C12 97.7(3) . . . . ? N1 Gd1 N3 C12 -158.1(2) . . . . ? C15 C14 N4 C13 177.6(3) . . . . ? C15 C14 N4 Gd1 0.2(5) . . . . ? C12 C13 N4 C14 -133.9(4) . . . . ? C12 C13 N4 Gd1 43.7(4) . . . . ? O2 Gd1 N4 C14 -65.1(3) . . . . ? O4 Gd1 N4 C14 79.0(3) . . . . ? O5 Gd1 N4 C14 104.9(3) . . . . ? O1 Gd1 N4 C14 -118.1(3) . . . . ? N3 Gd1 N4 C14 160.5(3) . . . . ? N2 Gd1 N4 C14 -175.1(3) . . . . ? N5 Gd1 N4 C14 3.4(3) . . . . ? N6 Gd1 N4 C14 17.7(4) . . . . ? N1 Gd1 N4 C14 -86.2(4) . . . . ? O2 Gd1 N4 C13 117.4(3) . . . . ? O4 Gd1 N4 C13 -98.4(3) . . . . ? O5 Gd1 N4 C13 -72.5(3) . . . . ? O1 Gd1 N4 C13 64.4(3) . . . . ? N3 Gd1 N4 C13 -16.9(3) . . . . ? N2 Gd1 N4 C13 7.5(3) . . . . ? N5 Gd1 N4 C13 -174.0(3) . . . . ? N6 Gd1 N4 C13 -159.7(3) . . . . ? N1 Gd1 N4 C13 96.4(3) . . . . ? C18 C19 N5 C15 -2.5(6) . . . . ? C20 C19 N5 C15 175.0(3) . . . . ? C18 C19 N5 Gd1 168.2(3) . . . . ? C20 C19 N5 Gd1 -14.3(4) . . . . ? C16 C15 N5 C19 0.1(6) . . . . ? C14 C15 N5 C19 -179.0(3) . . . . ? C16 C15 N5 Gd1 -170.9(3) . . . . ? C14 C15 N5 Gd1 10.0(4) . . . . ? O2 Gd1 N5 C19 -89.8(3) . . . . ? O4 Gd1 N5 C19 100.5(3) . . . . ? O5 Gd1 N5 C19 69.8(3) . . . . ? O1 Gd1 N5 C19 -117.8(3) . . . . ? N4 Gd1 N5 C19 -177.8(3) . . . . ? N3 Gd1 N5 C19 157.2(3) . . . . ? N6 Gd1 N5 C19 15.8(3) . . . . ? N1 Gd1 N5 C19 -33.5(3) . . . . ? O2 Gd1 N5 C15 80.9(3) . . . . ? O4 Gd1 N5 C15 -88.8(3) . . . . ? O5 Gd1 N5 C15 -119.5(3) . . . . ? O1 Gd1 N5 C15 52.9(3) . . . . ? N4 Gd1 N5 C15 -7.1(3) . . . . ? N3 Gd1 N5 C15 -32.1(3) . . . . ? N6 Gd1 N5 C15 -173.5(3) . . . . ? N1 Gd1 N5 C15 137.2(3) . . . . ? C23 C24 N6 C20 -0.9(6) . . . . ? C23 C24 N6 Gd1 166.5(3) . . . . ? C21 C20 N6 C24 1.2(6) . . . . ? C19 C20 N6 C24 -176.4(3) . . . . ? C21 C20 N6 Gd1 -166.0(3) . . . . ? C19 C20 N6 Gd1 16.4(4) . . . . ? O2 Gd1 N6 C24 -122.3(3) . . . . ? O4 Gd1 N6 C24 101.8(3) . . . . ? O5 Gd1 N6 C24 48.4(3) . . . . ? O1 Gd1 N6 C24 -95.6(3) . . . . ? N4 Gd1 N6 C24 162.1(3) . . . . ? N3 Gd1 N6 C24 68.4(3) . . . . ? N2 Gd1 N6 C24 -6.4(3) . . . . ? N5 Gd1 N6 C24 176.6(3) . . . . ? N1 Gd1 N6 C24 -51.9(3) . . . . ? O2 Gd1 N6 C20 44.8(3) . . . . ? O4 Gd1 N6 C20 -91.1(3) . . . . ? O5 Gd1 N6 C20 -144.5(3) . . . . ? O1 Gd1 N6 C20 71.4(3) . . . . ? N4 Gd1 N6 C20 -30.9(3) . . . . ? N3 Gd1 N6 C20 -124.6(3) . . . . ? N2 Gd1 N6 C20 160.6(3) . . . . ? N5 Gd1 N6 C20 -16.4(3) . . . . ? N1 Gd1 N6 C20 115.1(3) . . . . ? O3 N7 O1 Gd1 176.5(3) . . . . ? O2 N7 O1 Gd1 -3.6(3) . . . . ? O2 Gd1 O1 N7 2.12(18) . . . . ? O4 Gd1 O1 N7 117.4(2) . . . . ? O5 Gd1 O1 N7 -155.41(18) . . . . ? N4 Gd1 O1 N7 88.6(2) . . . . ? N3 Gd1 O1 N7 156.0(2) . . . . ? N2 Gd1 O1 N7 -138.0(2) . . . . ? N5 Gd1 O1 N7 35.2(2) . . . . ? N6 Gd1 O1 N7 -33.0(3) . . . . ? N1 Gd1 O1 N7 -74.4(2) . . . . ? O3 N7 O2 Gd1 -176.4(3) . . . . ? O1 N7 O2 Gd1 3.6(3) . . . . ? O4 Gd1 O2 N7 -133.86(19) . . . . ? O5 Gd1 O2 N7 126.2(3) . . . . ? O1 Gd1 O2 N7 -2.12(18) . . . . ? N4 Gd1 O2 N7 -81.7(2) . . . . ? N3 Gd1 O2 N7 -32.2(2) . . . . ? N2 Gd1 O2 N7 40.0(2) . . . . ? N5 Gd1 O2 N7 -147.6(2) . . . . ? N6 Gd1 O2 N7 154.7(2) . . . . ? N1 Gd1 O2 N7 86.5(2) . . . . ? O6 N8 O4 Gd1 171.5(3) . . . . ? O5 N8 O4 Gd1 -7.3(3) . . . . ? O2 Gd1 O4 N8 -151.69(18) . . . . ? O5 Gd1 O4 N8 4.24(18) . . . . ? O1 Gd1 O4 N8 126.2(2) . . . . ? N4 Gd1 O4 N8 155.0(2) . . . . ? N3 Gd1 O4 N8 87.6(2) . . . . ? N2 Gd1 O4 N8 34.4(2) . . . . ? N5 Gd1 O4 N8 -138.5(2) . . . . ? N6 Gd1 O4 N8 -74.2(2) . . . . ? N1 Gd1 O4 N8 -36.7(3) . . . . ? O6 N8 O5 Gd1 -171.5(3) . . . . ? O4 N8 O5 Gd1 7.2(3) . . . . ? O2 Gd1 O5 N8 111.8(3) . . . . ? O4 Gd1 O5 N8 -4.22(18) . . . . ? O1 Gd1 O5 N8 -135.46(19) . . . . ? N4 Gd1 O5 N8 -36.7(2) . . . . ? N3 Gd1 O5 N8 -87.0(2) . . . . ? N2 Gd1 O5 N8 -153.7(2) . . . . ? N5 Gd1 O5 N8 33.8(2) . . . . ? N6 Gd1 O5 N8 81.9(2) . . . . ? N1 Gd1 O5 N8 149.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 2.311 _refine_diff_density_min -1.227 _refine_diff_density_rms 0.122 _database_code_depnum_ccdc_archive 'CCDC 919428' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Ho_enbpy2_NO3_PF6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H20 Ho N8 O6, F6 P, 2(C2 H3 N)' _chemical_formula_sum 'C28 H26 F6 Ho N10 O6 P' _chemical_formula_weight 908.49 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 9.961(3) _cell_length_b 13.593(4) _cell_length_c 13.751(4) _cell_angle_alpha 68.307(3) _cell_angle_beta 86.035(3) _cell_angle_gamma 87.405(3) _cell_volume 1725.5(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 6568 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 26.47 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.749 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 2.428 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7431 _exptl_absorpt_correction_T_max 0.9530 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 19351 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 27.56 _reflns_number_total 7701 _reflns_number_gt 6463 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+3.1883P] 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 7701 _refine_ls_number_parameters 471 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.0897 _refine_ls_wR_factor_gt 0.0845 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2551(6) 0.6903(4) -0.1192(4) 0.0369(12) Uani 1 1 d . A 6 H1 H 0.1606 0.6987 -0.1093 0.044 Uiso 1 1 calc R A 6 C2 C 0.3083(7) 0.7016(4) -0.2196(4) 0.0497(15) Uani 1 1 d . A 6 H2 H 0.2526 0.7184 -0.2772 0.060 Uiso 1 1 calc R A 6 C3 C 0.4466(7) 0.6869(5) -0.2307(5) 0.0543(17) Uani 1 1 d . A 6 H3 H 0.4874 0.6949 -0.2977 0.065 Uiso 1 1 calc R A 6 C4 C 0.5257(6) 0.6607(5) -0.1455(5) 0.0470(15) Uani 1 1 d . A 6 H4 H 0.6200 0.6491 -0.1531 0.056 Uiso 1 1 calc R A 6 C5 C 0.4648(5) 0.6517(4) -0.0485(4) 0.0360(12) Uani 1 1 d . A 6 C6 C 0.5388(5) 0.6201(4) 0.0465(4) 0.0343(11) Uani 1 1 d . A 6 C7 C 0.6759(5) 0.5878(4) 0.0498(5) 0.0439(14) Uani 1 1 d . A 6 H7 H 0.7268 0.5912 -0.0124 0.053 Uiso 1 1 calc R A 6 C8 C 0.7344(5) 0.5508(4) 0.1461(5) 0.0475(15) Uani 1 1 d . A 6 H8 H 0.8258 0.5273 0.1503 0.057 Uiso 1 1 calc R A 6 C9 C 0.6611(5) 0.5482(4) 0.2343(5) 0.0436(14) Uani 1 1 d . A 6 H9 H 0.7001 0.5220 0.3005 0.052 Uiso 1 1 calc R A 6 C10 C 0.5280(5) 0.5848(4) 0.2257(4) 0.0345(11) Uani 1 1 d . A 6 C11 C 0.4437(5) 0.5866(4) 0.3158(4) 0.0341(11) Uani 1 1 d . A 6 H11 H 0.4750 0.5545 0.3845 0.041 Uiso 1 1 calc R A 6 C12 C 0.2416(5) 0.6290(4) 0.3933(4) 0.0372(12) Uani 1 1 d . A 6 H12A H 0.2305 0.7008 0.3955 0.045 Uiso 1 1 calc R A 6 H12B H 0.2808 0.5814 0.4589 0.045 Uiso 1 1 calc R A 6 C13 C 0.1073(5) 0.5884(4) 0.3806(4) 0.0357(12) Uani 1 1 d . A 6 H13A H 0.1166 0.5136 0.3865 0.043 Uiso 1 1 calc R A 6 H13B H 0.0402 0.5929 0.4355 0.043 Uiso 1 1 calc R A 6 C14 C -0.0540(5) 0.6942(4) 0.2662(4) 0.0307(11) Uani 1 1 d . A 6 H14 H -0.1170 0.6753 0.3249 0.037 Uiso 1 1 calc R A 6 C15 C -0.0937(4) 0.7677(4) 0.1640(4) 0.0264(10) Uani 1 1 d . A 6 C16 C -0.2259(5) 0.8026(4) 0.1454(4) 0.0342(12) Uani 1 1 d . A 6 H16 H -0.2941 0.7808 0.2004 0.041 Uiso 1 1 calc R A 6 C17 C -0.2570(5) 0.8694(4) 0.0458(5) 0.0377(12) Uani 1 1 d . A 6 H17 H -0.3473 0.8924 0.0306 0.045 Uiso 1 1 calc R A 6 C18 C -0.1547(4) 0.9020(4) -0.0310(4) 0.0316(11) Uani 1 1 d . A 6 H18 H -0.1739 0.9478 -0.1000 0.038 Uiso 1 1 calc R A 6 C19 C -0.0224(4) 0.8674(3) -0.0070(4) 0.0235(9) Uani 1 1 d . A 6 C20 C 0.0945(4) 0.9049(3) -0.0832(4) 0.0250(9) Uani 1 1 d . A 6 C21 C 0.0792(5) 0.9727(4) -0.1869(4) 0.0342(11) Uani 1 1 d . A 6 H21 H -0.0082 0.9941 -0.2115 0.041 Uiso 1 1 calc R A 6 C22 C 0.1925(5) 1.0087(4) -0.2539(4) 0.0387(12) Uani 1 1 d . A 6 H22 H 0.1841 1.0530 -0.3252 0.046 Uiso 1 1 calc R A 6 C23 C 0.3170(5) 0.9782(4) -0.2139(4) 0.0310(11) Uani 1 1 d . A 6 H23 H 0.3965 1.0035 -0.2567 0.037 Uiso 1 1 calc R A 6 C24 C 0.3250(4) 0.9103(4) -0.1107(4) 0.0262(10) Uani 1 1 d . A 6 H24 H 0.4116 0.8897 -0.0841 0.031 Uiso 1 1 calc R A 6 C25 C 0.1841(10) 0.9379(8) 0.4244(7) 0.090(3) Uani 1 1 d . B 6 C26 C 0.3206(11) 0.9435(13) 0.4402(12) 0.175(6) Uani 1 1 d . B 6 H26A H 0.3561 1.0109 0.3909 0.262 Uiso 1 1 calc R B 6 H26B H 0.3707 0.8848 0.4285 0.262 Uiso 1 1 calc R B 6 H26C H 0.3304 0.9389 0.5122 0.262 Uiso 1 1 calc R B 6 C27 C 1.0146(7) 0.6822(6) 0.6383(5) 0.0559(16) Uani 1 1 d . C 6 C28 C 0.9276(7) 0.7664(6) 0.6522(6) 0.0673(19) Uani 1 1 d . C 6 H28A H 0.8363 0.7400 0.6750 0.101 Uiso 1 1 calc R C 6 H28B H 0.9252 0.8270 0.5856 0.101 Uiso 1 1 calc R C 6 H28C H 0.9630 0.7887 0.7054 0.101 Uiso 1 1 calc R C 6 F1 F 0.3170(3) 0.3522(3) 0.4028(2) 0.0454(8) Uani 1 1 d . D 6 F2 F 0.2184(3) 0.2395(3) 0.5533(3) 0.0556(9) Uani 1 1 d . D 6 F3 F 0.4171(4) 0.2194(3) 0.6312(2) 0.0632(10) Uani 1 1 d . D 6 F4 F 0.5135(3) 0.3321(3) 0.4794(2) 0.0504(8) Uani 1 1 d . D 6 F5 F 0.3259(3) 0.3822(3) 0.5538(2) 0.0484(8) Uani 1 1 d . D 6 F6 F 0.4058(4) 0.1883(3) 0.4799(3) 0.0581(9) Uani 1 1 d . D 6 Ho1 Ho 0.235111(19) 0.704800(17) 0.125783(16) 0.02121(7) Uani 1 1 d . A 6 N1 N 0.3296(4) 0.6687(3) -0.0373(3) 0.0300(9) Uani 1 1 d . A 6 N2 N 0.4687(4) 0.6206(3) 0.1327(3) 0.0312(9) Uani 1 1 d . A 6 N3 N 0.3284(4) 0.6312(3) 0.3022(3) 0.0310(9) Uani 1 1 d . A 6 N4 N 0.0650(4) 0.6556(3) 0.2764(3) 0.0273(8) Uani 1 1 d . A 6 N5 N 0.0073(3) 0.7990(3) 0.0885(3) 0.0234(8) Uani 1 1 d . A 6 N6 N 0.2167(3) 0.8721(3) -0.0461(3) 0.0227(8) Uani 1 1 d . A 6 N7 N 0.1148(4) 0.5152(3) 0.1261(3) 0.0264(8) Uani 1 1 d . A 6 N8 N 0.3499(4) 0.8819(3) 0.1585(3) 0.0275(9) Uani 1 1 d . A 6 N9 N 0.0734(10) 0.9391(10) 0.4108(8) 0.150(4) Uani 1 1 d . B 6 N10 N 1.0833(6) 0.6145(6) 0.6290(4) 0.0658(16) Uani 1 1 d . C 6 O1 O 0.2184(3) 0.5113(2) 0.1770(2) 0.0296(7) Uani 1 1 d . A 6 O2 O 0.0644(3) 0.6074(2) 0.0788(2) 0.0271(7) Uani 1 1 d . A 6 O3 O 0.0658(3) 0.4356(3) 0.1225(3) 0.0366(8) Uani 1 1 d . A 6 O4 O 0.4179(3) 0.8263(3) 0.1145(2) 0.0294(7) Uani 1 1 d . A 6 O5 O 0.2307(3) 0.8510(2) 0.1900(2) 0.0279(7) Uani 1 1 d . A 6 O6 O 0.3963(3) 0.9584(3) 0.1688(3) 0.0405(9) Uani 1 1 d . A 6 P1 P 0.36669(14) 0.28506(11) 0.51651(10) 0.0361(3) Uani 1 1 d . D 6 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 C1 0.051(3) 0.026(3) 0.036(3) -0.015(2) 0.012(2) -0.007(2) C2 0.084(5) 0.037(3) 0.030(3) -0.016(3) 0.007(3) -0.013(3) C3 0.069(4) 0.048(4) 0.045(4) -0.021(3) 0.034(3) -0.014(3) C4 0.050(3) 0.046(3) 0.047(3) -0.022(3) 0.022(3) -0.005(3) C5 0.042(3) 0.023(2) 0.041(3) -0.013(2) 0.025(2) -0.008(2) C6 0.030(3) 0.025(2) 0.047(3) -0.013(2) 0.010(2) -0.005(2) C7 0.029(3) 0.034(3) 0.072(4) -0.027(3) 0.018(3) -0.003(2) C8 0.024(3) 0.033(3) 0.086(5) -0.022(3) -0.004(3) 0.001(2) C9 0.027(3) 0.032(3) 0.068(4) -0.015(3) -0.008(3) 0.003(2) C10 0.025(2) 0.025(3) 0.052(3) -0.011(2) -0.015(2) 0.0035(19) C11 0.030(3) 0.033(3) 0.036(3) -0.007(2) -0.009(2) -0.003(2) C12 0.038(3) 0.043(3) 0.023(2) -0.003(2) -0.001(2) -0.003(2) C13 0.036(3) 0.042(3) 0.022(2) -0.004(2) 0.002(2) -0.006(2) C14 0.026(2) 0.036(3) 0.031(3) -0.014(2) 0.0115(19) -0.007(2) C15 0.020(2) 0.029(2) 0.034(3) -0.016(2) 0.0057(18) -0.0024(18) C16 0.022(2) 0.033(3) 0.051(3) -0.022(3) 0.012(2) -0.005(2) C17 0.019(2) 0.032(3) 0.064(4) -0.019(3) -0.003(2) 0.001(2) C18 0.023(2) 0.027(2) 0.044(3) -0.011(2) -0.007(2) 0.0020(19) C19 0.020(2) 0.018(2) 0.033(2) -0.0098(19) -0.0028(18) 0.0011(16) C20 0.022(2) 0.021(2) 0.031(2) -0.0076(19) -0.0025(18) -0.0007(17) C21 0.031(3) 0.031(3) 0.035(3) -0.003(2) -0.008(2) -0.004(2) C22 0.046(3) 0.035(3) 0.024(2) 0.003(2) -0.002(2) -0.008(2) C23 0.030(2) 0.031(3) 0.028(2) -0.006(2) 0.0006(19) -0.006(2) C24 0.020(2) 0.028(2) 0.029(2) -0.010(2) 0.0036(18) -0.0026(18) C25 0.090(7) 0.118(8) 0.075(6) -0.047(6) -0.025(5) 0.017(6) C26 0.082(8) 0.277(19) 0.186(14) -0.112(14) -0.035(8) 0.048(10) C27 0.045(4) 0.077(5) 0.043(4) -0.018(3) -0.002(3) -0.006(3) C28 0.068(5) 0.063(5) 0.068(5) -0.019(4) -0.017(4) 0.005(4) F1 0.0444(18) 0.054(2) 0.0291(16) -0.0050(14) -0.0027(13) -0.0020(15) F2 0.056(2) 0.061(2) 0.047(2) -0.0188(17) 0.0222(16) -0.0210(17) F3 0.082(3) 0.067(2) 0.0242(16) 0.0020(16) -0.0033(16) 0.004(2) F4 0.0338(16) 0.075(2) 0.0369(17) -0.0145(16) 0.0055(13) -0.0052(16) F5 0.0508(19) 0.052(2) 0.0470(19) -0.0251(16) 0.0074(15) -0.0045(15) F6 0.073(2) 0.052(2) 0.051(2) -0.0228(17) 0.0044(18) 0.0097(18) Ho1 0.01277(10) 0.02482(11) 0.02262(11) -0.00532(8) 0.00179(7) 0.00046(7) N1 0.035(2) 0.028(2) 0.027(2) -0.0116(17) 0.0096(17) -0.0007(17) N2 0.024(2) 0.025(2) 0.040(2) -0.0094(18) 0.0054(17) -0.0009(16) N3 0.028(2) 0.031(2) 0.029(2) -0.0034(18) -0.0034(16) -0.0011(17) N4 0.029(2) 0.026(2) 0.024(2) -0.0058(16) 0.0006(16) -0.0061(16) N5 0.0164(17) 0.0220(19) 0.031(2) -0.0095(16) 0.0038(15) 0.0005(14) N6 0.0214(18) 0.0237(19) 0.0219(19) -0.0075(16) 0.0001(14) -0.0006(15) N7 0.0230(19) 0.031(2) 0.025(2) -0.0107(17) 0.0070(15) -0.0018(16) N8 0.0222(19) 0.030(2) 0.026(2) -0.0049(17) -0.0071(15) 0.0008(16) N9 0.107(7) 0.204(11) 0.107(7) -0.011(7) -0.045(6) -0.016(7) N10 0.052(3) 0.100(5) 0.053(3) -0.038(3) -0.005(3) 0.005(3) O1 0.0202(16) 0.0301(18) 0.0331(18) -0.0056(15) 0.0003(13) -0.0013(13) O2 0.0207(15) 0.0288(17) 0.0285(17) -0.0070(14) -0.0002(12) 0.0013(13) O3 0.039(2) 0.033(2) 0.041(2) -0.0164(16) 0.0026(16) -0.0083(16) O4 0.0167(15) 0.0361(19) 0.0311(18) -0.0074(15) -0.0018(13) -0.0004(13) O5 0.0229(16) 0.0287(17) 0.0298(17) -0.0083(14) 0.0003(13) -0.0019(13) O6 0.0341(19) 0.032(2) 0.055(2) -0.0116(18) -0.0154(17) -0.0054(15) P1 0.0416(7) 0.0390(8) 0.0220(6) -0.0058(6) 0.0066(5) -0.0007(6) _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 C1 N1 1.326(7) . ? C1 C2 1.400(7) . ? C1 H1 0.9500 . ? C2 C3 1.390(9) . ? C2 H2 0.9500 . ? C3 C4 1.384(9) . ? C3 H3 0.9500 . ? C4 C5 1.392(7) . ? C4 H4 0.9500 . ? C5 N1 1.364(6) . ? C5 C6 1.457(8) . ? C6 N2 1.335(6) . ? C6 C7 1.414(7) . ? C7 C8 1.391(9) . ? C7 H7 0.9500 . ? C8 C9 1.362(8) . ? C8 H8 0.9500 . ? C9 C10 1.392(7) . ? C9 H9 0.9500 . ? C10 N2 1.356(6) . ? C10 C11 1.456(7) . ? C11 N3 1.267(6) . ? C11 H11 0.9500 . ? C12 N3 1.463(6) . ? C12 C13 1.514(7) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.465(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.270(6) . ? C14 C15 1.460(7) . ? C14 H14 0.9500 . ? C15 N5 1.356(5) . ? C15 C16 1.387(6) . ? C16 C17 1.382(8) . ? C16 H16 0.9500 . ? C17 C18 1.377(7) . ? C17 H17 0.9500 . ? C18 C19 1.399(6) . ? C18 H18 0.9500 . ? C19 N5 1.343(6) . ? C19 C20 1.485(6) . ? C20 N6 1.345(5) . ? C20 C21 1.397(6) . ? C21 C22 1.391(7) . ? C21 H21 0.9500 . ? C22 C23 1.375(7) . ? C22 H22 0.9500 . ? C23 C24 1.384(6) . ? C23 H23 0.9500 . ? C24 N6 1.341(5) . ? C24 H24 0.9500 . ? C25 N9 1.130(11) . ? C25 C26 1.402(14) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 N10 1.161(8) . ? C27 C28 1.466(10) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? F1 P1 1.591(3) . ? F2 P1 1.603(3) . ? F3 P1 1.601(3) . ? F4 P1 1.597(3) . ? F5 P1 1.611(3) . ? F6 P1 1.598(4) . ? Ho1 O5 2.452(3) . ? Ho1 O2 2.460(3) . ? Ho1 O1 2.470(3) . ? Ho1 O4 2.472(3) . ? Ho1 N3 2.487(4) . ? Ho1 N4 2.490(4) . ? Ho1 N2 2.539(4) . ? Ho1 N5 2.543(3) . ? Ho1 N1 2.576(4) . ? Ho1 N6 2.616(4) . ? N7 O3 1.226(5) . ? N7 O1 1.274(5) . ? N7 O2 1.277(5) . ? N8 O6 1.216(5) . ? N8 O5 1.270(5) . ? N8 O4 1.277(5) . ? 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 N1 C1 C2 123.5(5) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C3 C2 C1 116.6(6) . . ? C3 C2 H2 121.7 . . ? C1 C2 H2 121.7 . . ? C4 C3 C2 120.8(5) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 118.8(5) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? N1 C5 C4 120.8(5) . . ? N1 C5 C6 116.4(4) . . ? C4 C5 C6 122.7(5) . . ? N2 C6 C7 121.0(5) . . ? N2 C6 C5 116.1(4) . . ? C7 C6 C5 122.9(5) . . ? C8 C7 C6 118.5(5) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C9 C8 C7 120.3(5) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C8 C9 C10 118.7(6) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? N2 C10 C9 122.0(5) . . ? N2 C10 C11 115.9(4) . . ? C9 C10 C11 122.1(5) . . ? N3 C11 C10 119.7(4) . . ? N3 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? N3 C12 C13 106.3(4) . . ? N3 C12 H12A 110.5 . . ? C13 C12 H12A 110.5 . . ? N3 C12 H12B 110.5 . . ? C13 C12 H12B 110.5 . . ? H12A C12 H12B 108.7 . . ? N4 C13 C12 106.6(4) . . ? N4 C13 H13A 110.4 . . ? C12 C13 H13A 110.4 . . ? N4 C13 H13B 110.4 . . ? C12 C13 H13B 110.4 . . ? H13A C13 H13B 108.6 . . ? N4 C14 C15 119.8(4) . . ? N4 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? N5 C15 C16 122.3(4) . . ? N5 C15 C14 115.4(4) . . ? C16 C15 C14 122.3(4) . . ? C17 C16 C15 119.1(4) . . ? C17 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C18 C17 C16 118.8(4) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C17 C18 C19 119.7(5) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? N5 C19 C18 121.6(4) . . ? N5 C19 C20 115.4(4) . . ? C18 C19 C20 123.0(4) . . ? N6 C20 C21 121.7(4) . . ? N6 C20 C19 116.2(4) . . ? C21 C20 C19 122.1(4) . . ? C22 C21 C20 119.7(4) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C23 C22 C21 118.1(4) . . ? C23 C22 H22 120.9 . . ? C21 C22 H22 120.9 . . ? C22 C23 C24 119.2(4) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? N6 C24 C23 123.4(4) . . ? N6 C24 H24 118.3 . . ? C23 C24 H24 118.3 . . ? N9 C25 C26 176.2(14) . . ? N10 C27 C28 178.9(7) . . ? O5 Ho1 O2 135.27(10) . . ? O5 Ho1 O1 145.02(10) . . ? O2 Ho1 O1 52.08(10) . . ? O5 Ho1 O4 51.65(10) . . ? O2 Ho1 O4 162.55(10) . . ? O1 Ho1 O4 134.99(10) . . ? O5 Ho1 N3 73.79(12) . . ? O2 Ho1 N3 120.20(12) . . ? O1 Ho1 N3 76.05(12) . . ? O4 Ho1 N3 76.03(12) . . ? O5 Ho1 N4 74.65(11) . . ? O2 Ho1 N4 75.26(11) . . ? O1 Ho1 N4 76.72(11) . . ? O4 Ho1 N4 120.35(12) . . ? N3 Ho1 N4 64.64(13) . . ? O5 Ho1 N2 111.14(12) . . ? O2 Ho1 N2 113.01(12) . . ? O1 Ho1 N2 70.00(11) . . ? O4 Ho1 N2 66.31(12) . . ? N3 Ho1 N2 64.50(13) . . ? N4 Ho1 N2 124.07(13) . . ? O5 Ho1 N5 72.35(11) . . ? O2 Ho1 N5 65.04(11) . . ? O1 Ho1 N5 112.10(11) . . ? O4 Ho1 N5 112.74(11) . . ? N3 Ho1 N5 124.18(12) . . ? N4 Ho1 N5 64.36(12) . . ? N2 Ho1 N5 171.21(12) . . ? O5 Ho1 N1 137.46(11) . . ? O2 Ho1 N1 72.39(12) . . ? O1 Ho1 N1 75.69(11) . . ? O4 Ho1 N1 93.18(12) . . ? N3 Ho1 N1 125.66(13) . . ? N4 Ho1 N1 146.13(13) . . ? N2 Ho1 N1 62.52(13) . . ? N5 Ho1 N1 109.26(13) . . ? O5 Ho1 N6 77.19(11) . . ? O2 Ho1 N6 93.88(11) . . ? O1 Ho1 N6 136.73(11) . . ? O4 Ho1 N6 71.12(11) . . ? N3 Ho1 N6 145.28(12) . . ? N4 Ho1 N6 124.59(12) . . ? N2 Ho1 N6 110.34(12) . . ? N5 Ho1 N6 61.98(11) . . ? N1 Ho1 N6 67.95(12) . . ? C1 N1 C5 119.3(4) . . ? C1 N1 Ho1 120.1(3) . . ? C5 N1 Ho1 118.7(3) . . ? C6 N2 C10 119.5(4) . . ? C6 N2 Ho1 122.0(3) . . ? C10 N2 Ho1 118.1(3) . . ? C11 N3 C12 119.5(4) . . ? C11 N3 Ho1 121.4(3) . . ? C12 N3 Ho1 118.7(3) . . ? C14 N4 C13 119.5(4) . . ? C14 N4 Ho1 121.4(3) . . ? C13 N4 Ho1 118.9(3) . . ? C19 N5 C15 118.4(4) . . ? C19 N5 Ho1 122.6(3) . . ? C15 N5 Ho1 118.3(3) . . ? C24 N6 C20 117.9(4) . . ? C24 N6 Ho1 121.3(3) . . ? C20 N6 Ho1 118.9(3) . . ? O3 N7 O1 122.4(4) . . ? O3 N7 O2 121.6(4) . . ? O1 N7 O2 116.0(4) . . ? O6 N8 O5 123.0(4) . . ? O6 N8 O4 122.3(4) . . ? O5 N8 O4 114.7(4) . . ? N7 O1 Ho1 95.7(2) . . ? N7 O2 Ho1 96.1(2) . . ? N8 O4 Ho1 96.2(2) . . ? N8 O5 Ho1 97.4(3) . . ? F1 P1 F4 89.53(17) . . ? F1 P1 F6 89.90(19) . . ? F4 P1 F6 90.6(2) . . ? F1 P1 F3 179.0(2) . . ? F4 P1 F3 90.06(19) . . ? F6 P1 F3 91.0(2) . . ? F1 P1 F2 90.03(18) . . ? F4 P1 F2 179.2(2) . . ? F6 P1 F2 90.1(2) . . ? F3 P1 F2 90.4(2) . . ? F1 P1 F5 90.12(18) . . ? F4 P1 F5 89.95(18) . . ? F6 P1 F5 179.5(2) . . ? F3 P1 F5 89.0(2) . . ? F2 P1 F5 89.38(18) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 3.002 _refine_diff_density_min -1.530 _refine_diff_density_rms 0.127 _database_code_depnum_ccdc_archive 'CCDC 919429' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Nd_enbpy2_NO3_PF6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H23 F6 N9 Nd O6 P' _chemical_formula_weight 846.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 8.949(2) _cell_length_b 12.231(3) _cell_length_c 16.394(4) _cell_angle_alpha 112.158(2) _cell_angle_beta 104.132(2) _cell_angle_gamma 92.428(3) _cell_volume 1593.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 9979 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.58 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.765 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 838 _exptl_absorpt_coefficient_mu 1.770 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8025 _exptl_absorpt_correction_T_max 0.9655 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 18075 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 27.60 _reflns_number_total 7154 _reflns_number_gt 6626 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ISOR restraints for F1, F4, and F5 atoms of the PF6 anion were used in order to address non-positive-definite errors. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+3.1662P] 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 7154 _refine_ls_number_parameters 443 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.0340 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8765(4) 0.6350(3) 0.3749(2) 0.0238(7) Uani 1 1 d . . . H1 H 0.9008 0.6500 0.3264 0.029 Uiso 1 1 calc R . . C2 C 0.8870(5) 0.7312(3) 0.4559(3) 0.0292(8) Uani 1 1 d . . . H2 H 0.9179 0.8104 0.4633 0.035 Uiso 1 1 calc R . . C3 C 0.8512(5) 0.7086(4) 0.5262(3) 0.0341(9) Uani 1 1 d . . . H3 H 0.8567 0.7727 0.5827 0.041 Uiso 1 1 calc R . . C4 C 0.8075(5) 0.5929(4) 0.5136(3) 0.0297(8) Uani 1 1 d . . . H4 H 0.7821 0.5765 0.5612 0.036 Uiso 1 1 calc R . . C5 C 0.8008(4) 0.4999(3) 0.4304(2) 0.0208(7) Uani 1 1 d . . . C6 C 0.7641(4) 0.3725(3) 0.4139(2) 0.0208(7) Uani 1 1 d . . . C7 C 0.7375(5) 0.3366(4) 0.4817(3) 0.0294(8) Uani 1 1 d . . . H7 H 0.7336 0.3943 0.5391 0.035 Uiso 1 1 calc R . . C8 C 0.7171(5) 0.2164(4) 0.4638(3) 0.0342(9) Uani 1 1 d . . . H8 H 0.6993 0.1906 0.5090 0.041 Uiso 1 1 calc R . . C9 C 0.7228(5) 0.1338(4) 0.3795(3) 0.0301(8) Uani 1 1 d . . . H9 H 0.7124 0.0508 0.3665 0.036 Uiso 1 1 calc R . . C10 C 0.7439(4) 0.1752(3) 0.3145(2) 0.0231(7) Uani 1 1 d . . . C11 C 0.7480(4) 0.0928(3) 0.2232(3) 0.0241(7) Uani 1 1 d . . . H11 H 0.7463 0.0100 0.2095 0.029 Uiso 1 1 calc R . . C12 C 0.7615(5) 0.0493(3) 0.0719(2) 0.0255(7) Uani 1 1 d . . . H12A H 0.6593 0.0332 0.0259 0.031 Uiso 1 1 calc R . . H12B H 0.7887 -0.0273 0.0741 0.031 Uiso 1 1 calc R . . C13 C 0.8855(4) 0.1072(3) 0.0459(2) 0.0248(7) Uani 1 1 d . . . H13A H 0.9896 0.1145 0.0875 0.030 Uiso 1 1 calc R . . H13B H 0.8861 0.0579 -0.0177 0.030 Uiso 1 1 calc R . . C14 C 0.8547(4) 0.2595(3) -0.0105(2) 0.0217(7) Uani 1 1 d . . . H14 H 0.8868 0.2094 -0.0615 0.026 Uiso 1 1 calc R . . C15 C 0.8116(4) 0.3762(3) -0.0051(2) 0.0194(6) Uani 1 1 d . . . C16 C 0.8321(4) 0.4202(3) -0.0688(2) 0.0232(7) Uani 1 1 d . . . H16 H 0.8730 0.3753 -0.1175 0.028 Uiso 1 1 calc R . . C17 C 0.7914(4) 0.5313(4) -0.0595(2) 0.0243(7) Uani 1 1 d . . . H17 H 0.8071 0.5652 -0.1008 0.029 Uiso 1 1 calc R . . C18 C 0.7275(4) 0.5927(3) 0.0105(2) 0.0220(7) Uani 1 1 d . . . H18 H 0.6995 0.6692 0.0181 0.026 Uiso 1 1 calc R . . C19 C 0.7048(4) 0.5403(3) 0.0701(2) 0.0175(6) Uani 1 1 d . . . C20 C 0.6241(4) 0.5965(3) 0.1417(2) 0.0175(6) Uani 1 1 d . . . C21 C 0.5673(4) 0.7042(3) 0.1540(3) 0.0230(7) Uani 1 1 d . . . H21 H 0.5832 0.7467 0.1181 0.028 Uiso 1 1 calc R . . C22 C 0.4876(4) 0.7483(3) 0.2190(3) 0.0265(8) Uani 1 1 d . . . H22 H 0.4500 0.8224 0.2292 0.032 Uiso 1 1 calc R . . C23 C 0.4628(4) 0.6841(3) 0.2690(3) 0.0251(7) Uani 1 1 d . . . H23 H 0.4051 0.7115 0.3126 0.030 Uiso 1 1 calc R . . C24 C 0.5242(4) 0.5783(3) 0.2540(2) 0.0206(7) Uani 1 1 d . . . H24 H 0.5084 0.5345 0.2890 0.025 Uiso 1 1 calc R . . C25 C 0.3616(4) 0.0560(4) 0.2068(3) 0.0286(8) Uani 1 1 d . . . C26 C 0.3088(6) 0.1464(4) 0.2769(3) 0.0396(10) Uani 1 1 d . . . H26A H 0.3310 0.1301 0.3324 0.059 Uiso 1 1 calc R . . H26B H 0.1964 0.1446 0.2542 0.059 Uiso 1 1 calc R . . H26C H 0.3635 0.2253 0.2911 0.059 Uiso 1 1 calc R . . F1 F 0.2020(4) 0.8840(3) 0.2677(3) 0.0782(11) Uani 1 1 d U . . F2 F -0.0396(7) 0.8788(5) 0.1869(3) 0.1054(16) Uani 1 1 d . . . F3 F -0.1297(4) 0.8680(3) 0.2997(2) 0.0572(8) Uani 1 1 d . . . F4 F 0.1061(5) 0.8703(5) 0.3794(3) 0.0986(14) Uani 1 1 d U . . F5 F 0.0115(6) 0.7353(3) 0.2358(3) 0.0909(13) Uani 1 1 d U . . F6 F 0.0475(4) 1.0174(2) 0.3263(3) 0.0675(10) Uani 1 1 d . . . N1 N 0.8338(3) 0.5214(3) 0.36093(19) 0.0203(6) Uani 1 1 d . . . N2 N 0.7643(3) 0.2929(3) 0.33119(19) 0.0197(6) Uani 1 1 d . . . N3 N 0.7539(3) 0.1320(3) 0.1625(2) 0.0218(6) Uani 1 1 d . . . N4 N 0.8490(3) 0.2260(3) 0.05334(19) 0.0204(6) Uani 1 1 d . . . N5 N 0.7484(3) 0.4347(2) 0.06346(18) 0.0175(5) Uani 1 1 d . . . N6 N 0.6048(3) 0.5348(2) 0.19266(19) 0.0180(5) Uani 1 1 d . . . N7 N 1.1024(3) 0.4222(3) 0.26046(19) 0.0210(6) Uani 1 1 d . . . N8 N 0.4214(3) 0.2564(2) 0.1208(2) 0.0197(6) Uani 1 1 d . . . N9 N 0.4046(4) -0.0150(3) 0.1526(2) 0.0348(8) Uani 1 1 d . . . Nd1 Nd 0.759152(19) 0.354369(15) 0.192297(11) 0.01490(6) Uani 1 1 d . . . O1 O 1.0175(3) 0.4735(2) 0.21537(17) 0.0227(5) Uani 1 1 d . . . O2 O 1.0351(3) 0.3309(2) 0.26378(17) 0.0225(5) Uani 1 1 d . . . O3 O 1.2406(3) 0.4599(3) 0.29952(18) 0.0302(6) Uani 1 1 d . . . O4 O 0.5045(3) 0.2465(2) 0.06593(16) 0.0225(5) Uani 1 1 d . . . O5 O 0.4931(3) 0.3031(2) 0.20625(16) 0.0211(5) Uani 1 1 d . . . O6 O 0.2810(3) 0.2235(2) 0.09314(19) 0.0270(6) Uani 1 1 d . . . P1 P 0.03995(15) 0.87866(10) 0.28715(9) 0.0396(3) 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 C1 0.0243(17) 0.0253(18) 0.0211(17) 0.0077(14) 0.0081(14) 0.0021(14) C2 0.031(2) 0.0244(18) 0.0270(19) 0.0041(15) 0.0098(16) -0.0003(15) C3 0.042(2) 0.030(2) 0.0231(19) -0.0008(16) 0.0150(17) 0.0023(17) C4 0.034(2) 0.036(2) 0.0179(17) 0.0077(16) 0.0103(15) 0.0028(16) C5 0.0173(15) 0.0283(18) 0.0161(15) 0.0079(14) 0.0051(12) 0.0050(13) C6 0.0186(16) 0.0289(18) 0.0166(16) 0.0113(14) 0.0039(12) 0.0044(13) C7 0.033(2) 0.039(2) 0.0200(18) 0.0143(16) 0.0099(15) 0.0047(16) C8 0.038(2) 0.045(2) 0.028(2) 0.0245(19) 0.0097(17) 0.0027(18) C9 0.033(2) 0.032(2) 0.032(2) 0.0205(17) 0.0080(16) 0.0037(16) C10 0.0198(16) 0.0267(18) 0.0253(18) 0.0142(15) 0.0042(14) 0.0054(14) C11 0.0248(17) 0.0199(16) 0.0275(18) 0.0111(14) 0.0042(14) 0.0047(13) C12 0.0324(19) 0.0179(16) 0.0223(17) 0.0041(14) 0.0063(15) 0.0077(14) C13 0.0295(19) 0.0214(17) 0.0212(17) 0.0042(14) 0.0086(14) 0.0126(14) C14 0.0204(16) 0.0276(18) 0.0150(15) 0.0042(13) 0.0076(13) 0.0064(13) C15 0.0150(15) 0.0271(17) 0.0146(15) 0.0070(13) 0.0036(12) 0.0019(13) C16 0.0192(16) 0.0332(19) 0.0169(16) 0.0093(14) 0.0059(13) 0.0022(14) C17 0.0193(16) 0.037(2) 0.0212(17) 0.0185(16) 0.0038(13) 0.0004(14) C18 0.0185(16) 0.0281(18) 0.0230(17) 0.0147(15) 0.0049(13) 0.0037(13) C19 0.0139(14) 0.0221(16) 0.0157(15) 0.0081(13) 0.0022(12) 0.0013(12) C20 0.0149(15) 0.0202(16) 0.0171(15) 0.0082(13) 0.0024(12) 0.0027(12) C21 0.0223(17) 0.0232(17) 0.0274(18) 0.0142(15) 0.0069(14) 0.0054(13) C22 0.0258(18) 0.0210(17) 0.0311(19) 0.0084(15) 0.0076(15) 0.0089(14) C23 0.0232(17) 0.0269(18) 0.0253(18) 0.0077(15) 0.0104(14) 0.0090(14) C24 0.0205(16) 0.0247(17) 0.0182(16) 0.0087(13) 0.0073(13) 0.0052(13) C25 0.0270(19) 0.032(2) 0.033(2) 0.0216(18) 0.0071(16) 0.0026(16) C26 0.050(3) 0.037(2) 0.050(3) 0.026(2) 0.031(2) 0.017(2) F1 0.072(2) 0.075(2) 0.134(3) 0.064(2) 0.068(2) 0.0349(17) F2 0.147(4) 0.133(4) 0.060(2) 0.047(3) 0.051(3) 0.055(3) F3 0.0499(17) 0.0471(17) 0.074(2) 0.0189(16) 0.0265(16) 0.0018(13) F4 0.079(2) 0.153(3) 0.089(2) 0.084(2) 0.0103(19) 0.018(2) F5 0.113(3) 0.0552(19) 0.117(3) 0.0221(19) 0.072(2) 0.0211(19) F6 0.0593(19) 0.0288(14) 0.115(3) 0.0169(17) 0.046(2) 0.0048(13) N1 0.0209(14) 0.0233(14) 0.0158(13) 0.0069(11) 0.0051(11) 0.0039(11) N2 0.0193(14) 0.0242(14) 0.0175(14) 0.0105(12) 0.0048(11) 0.0039(11) N3 0.0237(15) 0.0194(14) 0.0213(14) 0.0075(12) 0.0053(12) 0.0055(11) N4 0.0211(14) 0.0196(14) 0.0181(14) 0.0041(11) 0.0063(11) 0.0073(11) N5 0.0175(13) 0.0201(14) 0.0145(13) 0.0068(11) 0.0041(10) 0.0023(11) N6 0.0184(13) 0.0195(13) 0.0167(13) 0.0078(11) 0.0054(11) 0.0042(11) N7 0.0197(14) 0.0288(15) 0.0148(13) 0.0065(12) 0.0086(11) 0.0046(12) N8 0.0211(14) 0.0177(13) 0.0228(14) 0.0105(11) 0.0065(11) 0.0046(11) N9 0.0384(19) 0.0348(19) 0.0304(18) 0.0128(15) 0.0089(15) 0.0021(15) Nd1 0.01663(10) 0.01615(10) 0.01250(9) 0.00570(7) 0.00491(6) 0.00400(6) O1 0.0242(12) 0.0256(13) 0.0207(12) 0.0106(10) 0.0086(10) 0.0038(10) O2 0.0200(12) 0.0271(13) 0.0230(12) 0.0127(10) 0.0061(10) 0.0046(10) O3 0.0175(12) 0.0457(17) 0.0242(13) 0.0116(12) 0.0050(10) -0.0009(11) O4 0.0211(12) 0.0279(13) 0.0189(12) 0.0092(10) 0.0066(9) 0.0045(10) O5 0.0210(12) 0.0247(12) 0.0186(12) 0.0099(10) 0.0054(9) 0.0036(10) O6 0.0188(12) 0.0286(14) 0.0321(14) 0.0140(11) 0.0024(10) -0.0002(10) P1 0.0549(7) 0.0299(5) 0.0560(7) 0.0254(5) 0.0384(6) 0.0206(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 C1 N1 1.342(5) . ? C1 C2 1.382(5) . ? C1 H1 0.9500 . ? C2 C3 1.385(6) . ? C2 H2 0.9500 . ? C3 C4 1.376(6) . ? C3 H3 0.9500 . ? C4 C5 1.393(5) . ? C4 H4 0.9500 . ? C5 N1 1.356(4) . ? C5 C6 1.485(5) . ? C6 N2 1.339(4) . ? C6 C7 1.404(5) . ? C7 C8 1.381(6) . ? C7 H7 0.9500 . ? C8 C9 1.386(6) . ? C8 H8 0.9500 . ? C9 C10 1.388(5) . ? C9 H9 0.9500 . ? C10 N2 1.354(5) . ? C10 C11 1.466(5) . ? C11 N3 1.268(5) . ? C11 H11 0.9500 . ? C12 N3 1.468(4) . ? C12 C13 1.519(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.468(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.271(5) . ? C14 C15 1.470(5) . ? C14 H14 0.9500 . ? C15 N5 1.355(4) . ? C15 C16 1.386(5) . ? C16 C17 1.385(5) . ? C16 H16 0.9500 . ? C17 C18 1.383(5) . ? C17 H17 0.9500 . ? C18 C19 1.400(5) . ? C18 H18 0.9500 . ? C19 N5 1.339(4) . ? C19 C20 1.490(5) . ? C20 N6 1.353(4) . ? C20 C21 1.394(5) . ? C21 C22 1.381(5) . ? C21 H21 0.9500 . ? C22 C23 1.378(5) . ? C22 H22 0.9500 . ? C23 C24 1.386(5) . ? C23 H23 0.9500 . ? C24 N6 1.341(4) . ? C24 H24 0.9500 . ? C25 N9 1.141(5) . ? C25 C26 1.455(6) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? F1 P1 1.563(3) . ? F2 P1 1.624(4) . ? F3 P1 1.587(3) . ? F4 P1 1.527(4) . ? F5 P1 1.610(4) . ? F6 P1 1.563(3) . ? N1 Nd1 2.643(3) . ? N2 Nd1 2.645(3) . ? N3 Nd1 2.571(3) . ? N4 Nd1 2.570(3) . ? N5 Nd1 2.628(3) . ? N6 Nd1 2.651(3) . ? N7 O3 1.222(4) . ? N7 O2 1.272(4) . ? N7 O1 1.278(4) . ? N8 O6 1.220(4) . ? N8 O5 1.275(4) . ? N8 O4 1.276(4) . ? Nd1 O5 2.523(2) . ? Nd1 O2 2.541(2) . ? Nd1 O1 2.546(3) . ? Nd1 O4 2.570(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 N1 C1 C2 123.5(3) . . ? N1 C1 H1 118.3 . . ? C2 C1 H1 118.3 . . ? C1 C2 C3 118.0(4) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 119.6(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 119.5(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 121.2(3) . . ? N1 C5 C6 116.2(3) . . ? C4 C5 C6 122.5(3) . . ? N2 C6 C7 121.6(3) . . ? N2 C6 C5 115.8(3) . . ? C7 C6 C5 122.5(3) . . ? C8 C7 C6 119.2(4) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? C7 C8 C9 119.4(4) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C10 118.3(4) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? N2 C10 C9 122.8(3) . . ? N2 C10 C11 115.9(3) . . ? C9 C10 C11 121.3(3) . . ? N3 C11 C10 120.0(3) . . ? N3 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? N3 C12 C13 107.8(3) . . ? N3 C12 H12A 110.2 . . ? C13 C12 H12A 110.2 . . ? N3 C12 H12B 110.2 . . ? C13 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? N4 C13 C12 108.0(3) . . ? N4 C13 H13A 110.1 . . ? C12 C13 H13A 110.1 . . ? N4 C13 H13B 110.1 . . ? C12 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? N4 C14 C15 119.7(3) . . ? N4 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? N5 C15 C16 123.1(3) . . ? N5 C15 C14 116.0(3) . . ? C16 C15 C14 120.8(3) . . ? C17 C16 C15 118.2(3) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C18 C17 C16 119.4(3) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 119.1(3) . . ? C17 C18 H18 120.5 . . ? C19 C18 H18 120.5 . . ? N5 C19 C18 122.0(3) . . ? N5 C19 C20 116.1(3) . . ? C18 C19 C20 121.9(3) . . ? N6 C20 C21 121.7(3) . . ? N6 C20 C19 116.0(3) . . ? C21 C20 C19 122.2(3) . . ? C22 C21 C20 119.1(3) . . ? C22 C21 H21 120.5 . . ? C20 C21 H21 120.5 . . ? C23 C22 C21 119.6(3) . . ? C23 C22 H22 120.2 . . ? C21 C22 H22 120.2 . . ? C22 C23 C24 118.2(3) . . ? C22 C23 H23 120.9 . . ? C24 C23 H23 120.9 . . ? N6 C24 C23 123.4(3) . . ? N6 C24 H24 118.3 . . ? C23 C24 H24 118.3 . . ? N9 C25 C26 179.2(5) . . ? C1 N1 C5 118.2(3) . . ? C1 N1 Nd1 119.2(2) . . ? C5 N1 Nd1 121.2(2) . . ? C6 N2 C10 118.6(3) . . ? C6 N2 Nd1 122.2(2) . . ? C10 N2 Nd1 118.5(2) . . ? C11 N3 C12 119.7(3) . . ? C11 N3 Nd1 122.5(2) . . ? C12 N3 Nd1 117.8(2) . . ? C14 N4 C13 119.6(3) . . ? C14 N4 Nd1 122.2(2) . . ? C13 N4 Nd1 118.1(2) . . ? C19 N5 C15 118.1(3) . . ? C19 N5 Nd1 122.5(2) . . ? C15 N5 Nd1 118.6(2) . . ? C24 N6 C20 118.0(3) . . ? C24 N6 Nd1 120.0(2) . . ? C20 N6 Nd1 121.2(2) . . ? O3 N7 O2 121.7(3) . . ? O3 N7 O1 121.8(3) . . ? O2 N7 O1 116.6(3) . . ? O6 N8 O5 121.8(3) . . ? O6 N8 O4 121.9(3) . . ? O5 N8 O4 116.4(3) . . ? O5 Nd1 O2 135.23(8) . . ? O5 Nd1 O1 160.90(8) . . ? O2 Nd1 O1 50.48(8) . . ? O5 Nd1 O4 50.39(8) . . ? O2 Nd1 O4 144.37(8) . . ? O1 Nd1 O4 139.81(8) . . ? O5 Nd1 N4 121.24(9) . . ? O2 Nd1 N4 76.43(9) . . ? O1 Nd1 N4 76.73(9) . . ? O4 Nd1 N4 75.72(9) . . ? O5 Nd1 N3 78.74(9) . . ? O2 Nd1 N3 73.69(9) . . ? O1 Nd1 N3 117.76(9) . . ? O4 Nd1 N3 74.40(9) . . ? N4 Nd1 N3 64.17(9) . . ? O5 Nd1 N5 112.90(8) . . ? O2 Nd1 N5 111.63(8) . . ? O1 Nd1 N5 67.69(8) . . ? O4 Nd1 N5 73.82(8) . . ? N4 Nd1 N5 62.62(9) . . ? N3 Nd1 N5 122.83(9) . . ? O5 Nd1 N1 89.73(8) . . ? O2 Nd1 N1 75.89(8) . . ? O1 Nd1 N1 73.66(8) . . ? O4 Nd1 N1 135.72(8) . . ? N4 Nd1 N1 148.18(9) . . ? N3 Nd1 N1 121.33(9) . . ? N5 Nd1 N1 114.71(9) . . ? O5 Nd1 N2 65.83(8) . . ? O2 Nd1 N2 70.24(8) . . ? O1 Nd1 N2 111.70(8) . . ? O4 Nd1 N2 107.69(8) . . ? N4 Nd1 N2 122.57(9) . . ? N3 Nd1 N2 62.29(9) . . ? N5 Nd1 N2 174.73(8) . . ? N1 Nd1 N2 60.58(9) . . ? O5 Nd1 N6 72.73(8) . . ? O2 Nd1 N6 136.29(8) . . ? O1 Nd1 N6 92.56(8) . . ? O4 Nd1 N6 78.20(8) . . ? N4 Nd1 N6 122.15(9) . . ? N3 Nd1 N6 149.03(9) . . ? N5 Nd1 N6 60.82(9) . . ? N1 Nd1 N6 70.98(9) . . ? N2 Nd1 N6 114.28(9) . . ? N7 O1 Nd1 95.86(18) . . ? N7 O2 Nd1 96.26(18) . . ? N8 O4 Nd1 95.37(18) . . ? N8 O5 Nd1 97.67(18) . . ? F4 P1 F6 96.4(3) . . ? F4 P1 F1 93.9(2) . . ? F6 P1 F1 93.13(19) . . ? F4 P1 F3 89.2(2) . . ? F6 P1 F3 88.80(17) . . ? F1 P1 F3 176.1(2) . . ? F4 P1 F5 90.4(3) . . ? F6 P1 F5 172.1(3) . . ? F1 P1 F5 90.5(2) . . ? F3 P1 F5 87.2(2) . . ? F4 P1 F2 175.8(3) . . ? F6 P1 F2 86.8(2) . . ? F1 P1 F2 88.7(3) . . ? F3 P1 F2 88.1(2) . . ? F5 P1 F2 86.2(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -0.1(6) . . . . ? C1 C2 C3 C4 0.3(6) . . . . ? C2 C3 C4 C5 0.4(6) . . . . ? C3 C4 C5 N1 -1.2(6) . . . . ? C3 C4 C5 C6 176.2(4) . . . . ? N1 C5 C6 N2 -1.5(4) . . . . ? C4 C5 C6 N2 -179.0(3) . . . . ? N1 C5 C6 C7 175.8(3) . . . . ? C4 C5 C6 C7 -1.6(5) . . . . ? N2 C6 C7 C8 2.6(6) . . . . ? C5 C6 C7 C8 -174.6(4) . . . . ? C6 C7 C8 C9 -0.2(6) . . . . ? C7 C8 C9 C10 -2.1(6) . . . . ? C8 C9 C10 N2 2.2(6) . . . . ? C8 C9 C10 C11 -178.8(4) . . . . ? N2 C10 C11 N3 -7.1(5) . . . . ? C9 C10 C11 N3 173.9(4) . . . . ? N3 C12 C13 N4 -53.7(4) . . . . ? N4 C14 C15 N5 -8.3(5) . . . . ? N4 C14 C15 C16 173.3(3) . . . . ? N5 C15 C16 C17 2.5(5) . . . . ? C14 C15 C16 C17 -179.1(3) . . . . ? C15 C16 C17 C18 -2.1(5) . . . . ? C16 C17 C18 C19 -0.4(5) . . . . ? C17 C18 C19 N5 2.6(5) . . . . ? C17 C18 C19 C20 -174.6(3) . . . . ? N5 C19 C20 N6 0.4(4) . . . . ? C18 C19 C20 N6 177.7(3) . . . . ? N5 C19 C20 C21 -177.6(3) . . . . ? C18 C19 C20 C21 -0.2(5) . . . . ? N6 C20 C21 C22 -0.8(5) . . . . ? C19 C20 C21 C22 177.1(3) . . . . ? C20 C21 C22 C23 -1.4(5) . . . . ? C21 C22 C23 C24 2.1(6) . . . . ? C22 C23 C24 N6 -0.8(6) . . . . ? C2 C1 N1 C5 -0.7(5) . . . . ? C2 C1 N1 Nd1 166.4(3) . . . . ? C4 C5 N1 C1 1.3(5) . . . . ? C6 C5 N1 C1 -176.2(3) . . . . ? C4 C5 N1 Nd1 -165.5(3) . . . . ? C6 C5 N1 Nd1 17.0(4) . . . . ? C7 C6 N2 C10 -2.5(5) . . . . ? C5 C6 N2 C10 174.9(3) . . . . ? C7 C6 N2 Nd1 167.8(3) . . . . ? C5 C6 N2 Nd1 -14.8(4) . . . . ? C9 C10 N2 C6 0.0(5) . . . . ? C11 C10 N2 C6 -179.0(3) . . . . ? C9 C10 N2 Nd1 -170.6(3) . . . . ? C11 C10 N2 Nd1 10.3(4) . . . . ? C10 C11 N3 C12 178.6(3) . . . . ? C10 C11 N3 Nd1 0.0(5) . . . . ? C13 C12 N3 C11 -135.0(3) . . . . ? C13 C12 N3 Nd1 43.7(3) . . . . ? C15 C14 N4 C13 177.3(3) . . . . ? C15 C14 N4 Nd1 1.1(4) . . . . ? C12 C13 N4 C14 -134.2(3) . . . . ? C12 C13 N4 Nd1 42.1(3) . . . . ? C18 C19 N5 C15 -2.2(5) . . . . ? C20 C19 N5 C15 175.2(3) . . . . ? C18 C19 N5 Nd1 167.5(2) . . . . ? C20 C19 N5 Nd1 -15.1(4) . . . . ? C16 C15 N5 C19 -0.4(5) . . . . ? C14 C15 N5 C19 -178.8(3) . . . . ? C16 C15 N5 Nd1 -170.5(3) . . . . ? C14 C15 N5 Nd1 11.1(4) . . . . ? C23 C24 N6 C20 -1.3(5) . . . . ? C23 C24 N6 Nd1 168.7(3) . . . . ? C21 C20 N6 C24 2.1(5) . . . . ? C19 C20 N6 C24 -175.9(3) . . . . ? C21 C20 N6 Nd1 -167.8(2) . . . . ? C19 C20 N6 Nd1 14.2(4) . . . . ? C14 N4 Nd1 O5 104.6(3) . . . . ? C13 N4 Nd1 O5 -71.6(3) . . . . ? C14 N4 Nd1 O2 -120.3(3) . . . . ? C13 N4 Nd1 O2 63.4(2) . . . . ? C14 N4 Nd1 O1 -68.3(3) . . . . ? C13 N4 Nd1 O1 115.4(2) . . . . ? C14 N4 Nd1 O4 82.1(3) . . . . ? C13 N4 Nd1 O4 -94.1(2) . . . . ? C14 N4 Nd1 N3 161.4(3) . . . . ? C13 N4 Nd1 N3 -14.8(2) . . . . ? C14 N4 Nd1 N5 3.2(3) . . . . ? C13 N4 Nd1 N5 -173.1(3) . . . . ? C14 N4 Nd1 N1 -90.2(3) . . . . ? C13 N4 Nd1 N1 93.6(3) . . . . ? C14 N4 Nd1 N2 -175.8(3) . . . . ? C13 N4 Nd1 N2 8.0(3) . . . . ? C14 N4 Nd1 N6 16.3(3) . . . . ? C13 N4 Nd1 N6 -160.0(2) . . . . ? C11 N3 Nd1 O5 -64.8(3) . . . . ? C12 N3 Nd1 O5 116.6(2) . . . . ? C11 N3 Nd1 O2 79.5(3) . . . . ? C12 N3 Nd1 O2 -99.1(2) . . . . ? C11 N3 Nd1 O1 105.0(3) . . . . ? C12 N3 Nd1 O1 -73.7(3) . . . . ? C11 N3 Nd1 O4 -116.5(3) . . . . ? C12 N3 Nd1 O4 64.8(2) . . . . ? C11 N3 Nd1 N4 162.1(3) . . . . ? C12 N3 Nd1 N4 -16.6(2) . . . . ? C11 N3 Nd1 N5 -174.9(3) . . . . ? C12 N3 Nd1 N5 6.4(3) . . . . ? C11 N3 Nd1 N1 17.9(3) . . . . ? C12 N3 Nd1 N1 -160.7(2) . . . . ? C11 N3 Nd1 N2 3.7(3) . . . . ? C12 N3 Nd1 N2 -175.0(3) . . . . ? C11 N3 Nd1 N6 -87.9(3) . . . . ? C12 N3 Nd1 N6 93.4(3) . . . . ? C19 N5 Nd1 O5 68.3(3) . . . . ? C15 N5 Nd1 O5 -122.0(2) . . . . ? C19 N5 Nd1 O2 -116.5(2) . . . . ? C15 N5 Nd1 O2 53.2(2) . . . . ? C19 N5 Nd1 O1 -91.0(2) . . . . ? C15 N5 Nd1 O1 78.7(2) . . . . ? C19 N5 Nd1 O4 100.9(2) . . . . ? C15 N5 Nd1 O4 -89.5(2) . . . . ? C19 N5 Nd1 N4 -177.1(3) . . . . ? C15 N5 Nd1 N4 -7.5(2) . . . . ? C19 N5 Nd1 N3 159.5(2) . . . . ? C15 N5 Nd1 N3 -30.9(3) . . . . ? C19 N5 Nd1 N1 -32.6(3) . . . . ? C15 N5 Nd1 N1 137.1(2) . . . . ? C19 N5 Nd1 N6 15.5(2) . . . . ? C15 N5 Nd1 N6 -174.8(3) . . . . ? C1 N1 Nd1 O5 -121.4(3) . . . . ? C5 N1 Nd1 O5 45.3(3) . . . . ? C1 N1 Nd1 O2 101.4(3) . . . . ? C5 N1 Nd1 O2 -91.9(3) . . . . ? C1 N1 Nd1 O1 49.0(2) . . . . ? C5 N1 Nd1 O1 -144.3(3) . . . . ? C1 N1 Nd1 O4 -98.1(3) . . . . ? C5 N1 Nd1 O4 68.6(3) . . . . ? C1 N1 Nd1 N4 71.2(3) . . . . ? C5 N1 Nd1 N4 -122.1(3) . . . . ? C1 N1 Nd1 N3 162.0(2) . . . . ? C5 N1 Nd1 N3 -31.3(3) . . . . ? C1 N1 Nd1 N5 -6.2(3) . . . . ? C5 N1 Nd1 N5 160.5(2) . . . . ? C1 N1 Nd1 N2 176.5(3) . . . . ? C5 N1 Nd1 N2 -16.9(2) . . . . ? C1 N1 Nd1 N6 -49.6(2) . . . . ? C5 N1 Nd1 N6 117.1(3) . . . . ? C6 N2 Nd1 O5 -88.0(3) . . . . ? C10 N2 Nd1 O5 82.3(2) . . . . ? C6 N2 Nd1 O2 100.9(3) . . . . ? C10 N2 Nd1 O2 -88.8(2) . . . . ? C6 N2 Nd1 O1 71.4(3) . . . . ? C10 N2 Nd1 O1 -118.3(2) . . . . ? C6 N2 Nd1 O4 -116.8(3) . . . . ? C10 N2 Nd1 O4 53.5(3) . . . . ? C6 N2 Nd1 N4 159.2(2) . . . . ? C10 N2 Nd1 N4 -30.5(3) . . . . ? C6 N2 Nd1 N3 -177.7(3) . . . . ? C10 N2 Nd1 N3 -7.3(2) . . . . ? C6 N2 Nd1 N1 16.3(2) . . . . ? C10 N2 Nd1 N1 -173.4(3) . . . . ? C6 N2 Nd1 N6 -32.0(3) . . . . ? C10 N2 Nd1 N6 138.3(2) . . . . ? C24 N6 Nd1 O5 45.4(2) . . . . ? C20 N6 Nd1 O5 -144.8(3) . . . . ? C24 N6 Nd1 O2 -93.2(3) . . . . ? C20 N6 Nd1 O2 76.5(3) . . . . ? C24 N6 Nd1 O1 -122.2(2) . . . . ? C20 N6 Nd1 O1 47.6(2) . . . . ? C24 N6 Nd1 O4 97.3(3) . . . . ? C20 N6 Nd1 O4 -92.9(2) . . . . ? C24 N6 Nd1 N4 161.9(2) . . . . ? C20 N6 Nd1 N4 -28.4(3) . . . . ? C24 N6 Nd1 N3 69.2(3) . . . . ? C20 N6 Nd1 N3 -121.1(3) . . . . ? C24 N6 Nd1 N5 175.2(3) . . . . ? C20 N6 Nd1 N5 -15.0(2) . . . . ? C24 N6 Nd1 N1 -50.4(2) . . . . ? C20 N6 Nd1 N1 119.3(3) . . . . ? C24 N6 Nd1 N2 -6.9(3) . . . . ? C20 N6 Nd1 N2 162.8(2) . . . . ? O3 N7 O1 Nd1 -169.8(3) . . . . ? O2 N7 O1 Nd1 9.1(3) . . . . ? O5 Nd1 O1 N7 110.2(3) . . . . ? O2 Nd1 O1 N7 -5.29(16) . . . . ? O4 Nd1 O1 N7 -136.30(17) . . . . ? N4 Nd1 O1 N7 -88.51(18) . . . . ? N3 Nd1 O1 N7 -37.6(2) . . . . ? N5 Nd1 O1 N7 -154.1(2) . . . . ? N1 Nd1 O1 N7 79.70(18) . . . . ? N2 Nd1 O1 N7 31.6(2) . . . . ? N6 Nd1 O1 N7 149.02(18) . . . . ? O3 N7 O2 Nd1 169.8(3) . . . . ? O1 N7 O2 Nd1 -9.2(3) . . . . ? O5 Nd1 O2 N7 -149.89(17) . . . . ? O1 Nd1 O2 N7 5.31(16) . . . . ? O4 Nd1 O2 N7 128.60(18) . . . . ? N4 Nd1 O2 N7 89.17(19) . . . . ? N3 Nd1 O2 N7 155.8(2) . . . . ? N5 Nd1 O2 N7 36.4(2) . . . . ? N1 Nd1 O2 N7 -74.97(18) . . . . ? N2 Nd1 O2 N7 -138.4(2) . . . . ? N6 Nd1 O2 N7 -33.5(2) . . . . ? O6 N8 O4 Nd1 175.5(3) . . . . ? O5 N8 O4 Nd1 -4.2(3) . . . . ? O5 Nd1 O4 N8 2.46(16) . . . . ? O2 Nd1 O4 N8 117.75(19) . . . . ? O1 Nd1 O4 N8 -154.62(17) . . . . ? N4 Nd1 O4 N8 157.32(19) . . . . ? N3 Nd1 O4 N8 90.63(19) . . . . ? N5 Nd1 O4 N8 -137.53(19) . . . . ? N1 Nd1 O4 N8 -28.5(2) . . . . ? N2 Nd1 O4 N8 37.19(19) . . . . ? N6 Nd1 O4 N8 -74.79(18) . . . . ? O6 N8 O5 Nd1 -175.4(3) . . . . ? O4 N8 O5 Nd1 4.3(3) . . . . ? O2 Nd1 O5 N8 -134.06(17) . . . . ? O1 Nd1 O5 N8 127.3(2) . . . . ? O4 Nd1 O5 N8 -2.47(16) . . . . ? N4 Nd1 O5 N8 -31.3(2) . . . . ? N3 Nd1 O5 N8 -81.45(18) . . . . ? N5 Nd1 O5 N8 39.6(2) . . . . ? N1 Nd1 O5 N8 156.48(18) . . . . ? N2 Nd1 O5 N8 -146.0(2) . . . . ? N6 Nd1 O5 N8 86.34(18) . . . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 2.110 _refine_diff_density_min -1.090 _refine_diff_density_rms 0.111 _database_code_depnum_ccdc_archive 'CCDC 919430' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Tb_enbpy2_NO3_PF6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H23 F6 N9 O6 P Tb' _chemical_formula_weight 861.42 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0172(11) _cell_length_b 12.2389(15) _cell_length_c 16.133(2) _cell_angle_alpha 112.0540(10) _cell_angle_beta 104.2690(10) _cell_angle_gamma 91.6220(10) _cell_volume 1584.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 5833 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.54 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 2.373 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6233 _exptl_absorpt_correction_T_max 0.8328 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 17969 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.54 _reflns_number_total 7110 _reflns_number_gt 6668 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ISOR restraints for F2 and F5 atoms of the PF6 anion were used in order to address non-positive-definite errors. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0463P)^2^+2.9957P] 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 7110 _refine_ls_number_parameters 443 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.8749(4) 0.6325(3) 0.3679(2) 0.0242(7) Uani 1 1 d . . . H1 H 0.8983 0.6453 0.3177 0.029 Uiso 1 1 calc R . . C2 C 0.8856(5) 0.7300(3) 0.4491(3) 0.0305(8) Uani 1 1 d . . . H2 H 0.9147 0.8081 0.4543 0.037 Uiso 1 1 calc R . . C3 C 0.8533(5) 0.7116(4) 0.5225(3) 0.0368(10) Uani 1 1 d . . . H3 H 0.8596 0.7771 0.5791 0.044 Uiso 1 1 calc R . . C4 C 0.8117(5) 0.5975(4) 0.5130(3) 0.0309(8) Uani 1 1 d . . . H4 H 0.7890 0.5835 0.5629 0.037 Uiso 1 1 calc R . . C5 C 0.8033(4) 0.5029(3) 0.4293(2) 0.0218(7) Uani 1 1 d . . . C6 C 0.7670(4) 0.3777(3) 0.4154(2) 0.0220(7) Uani 1 1 d . . . C7 C 0.7435(5) 0.3440(4) 0.4860(3) 0.0307(8) Uani 1 1 d . . . H7 H 0.7417 0.4028 0.5442 0.037 Uiso 1 1 calc R . . C8 C 0.7233(5) 0.2254(4) 0.4701(3) 0.0354(9) Uani 1 1 d . . . H8 H 0.7083 0.2017 0.5175 0.042 Uiso 1 1 calc R . . C9 C 0.7248(5) 0.1404(4) 0.3841(3) 0.0315(8) Uani 1 1 d . . . H9 H 0.7132 0.0580 0.3720 0.038 Uiso 1 1 calc R . . C10 C 0.7438(4) 0.1799(3) 0.3165(2) 0.0234(7) Uani 1 1 d . . . C11 C 0.7453(4) 0.0960(3) 0.2236(3) 0.0243(7) Uani 1 1 d . . . H11 H 0.7429 0.0133 0.2100 0.029 Uiso 1 1 calc R . . C12 C 0.7576(5) 0.0519(3) 0.0703(3) 0.0268(8) Uani 1 1 d . . . H12A H 0.6571 0.0376 0.0233 0.032 Uiso 1 1 calc R . . H12B H 0.7832 -0.0252 0.0727 0.032 Uiso 1 1 calc R . . C13 C 0.8828(4) 0.1083(3) 0.0450(3) 0.0261(8) Uani 1 1 d . . . H13A H 0.9853 0.1132 0.0874 0.031 Uiso 1 1 calc R . . H13B H 0.8842 0.0600 -0.0196 0.031 Uiso 1 1 calc R . . C14 C 0.8542(4) 0.2619(3) -0.0104(2) 0.0226(7) Uani 1 1 d . . . H14 H 0.8872 0.2126 -0.0620 0.027 Uiso 1 1 calc R . . C15 C 0.8100(4) 0.3789(3) -0.0039(2) 0.0204(7) Uani 1 1 d . . . C16 C 0.8315(4) 0.4264(4) -0.0663(2) 0.0247(7) Uani 1 1 d . . . H16 H 0.8741 0.3835 -0.1155 0.030 Uiso 1 1 calc R . . C17 C 0.7892(4) 0.5380(4) -0.0554(3) 0.0249(7) Uani 1 1 d . . . H17 H 0.8050 0.5740 -0.0960 0.030 Uiso 1 1 calc R . . C18 C 0.7236(4) 0.5960(3) 0.0156(2) 0.0227(7) Uani 1 1 d . . . H18 H 0.6948 0.6728 0.0247 0.027 Uiso 1 1 calc R . . C19 C 0.7001(4) 0.5405(3) 0.0738(2) 0.0183(6) Uani 1 1 d . . . C20 C 0.6181(4) 0.5926(3) 0.1460(2) 0.0182(6) Uani 1 1 d . . . C21 C 0.5603(4) 0.7005(3) 0.1610(3) 0.0234(7) Uani 1 1 d . . . H21 H 0.5770 0.7460 0.1269 0.028 Uiso 1 1 calc R . . C22 C 0.4782(4) 0.7408(3) 0.2262(3) 0.0275(8) Uani 1 1 d . . . H22 H 0.4390 0.8148 0.2380 0.033 Uiso 1 1 calc R . . C23 C 0.4541(4) 0.6726(3) 0.2737(3) 0.0249(7) Uani 1 1 d . . . H23 H 0.3957 0.6975 0.3177 0.030 Uiso 1 1 calc R . . C24 C 0.5166(4) 0.5666(3) 0.2563(2) 0.0203(6) Uani 1 1 d . . . H24 H 0.5004 0.5199 0.2897 0.024 Uiso 1 1 calc R . . C25 C 0.6354(4) 0.9478(4) 0.7914(3) 0.0286(8) Uani 1 1 d . . . C26 C 0.6917(5) 0.8544(4) 0.7240(3) 0.0389(10) Uani 1 1 d . . . H26A H 0.6515 0.7766 0.7197 0.058 Uiso 1 1 calc R . . H26B H 0.8048 0.8649 0.7440 0.058 Uiso 1 1 calc R . . H26C H 0.6566 0.8588 0.6629 0.058 Uiso 1 1 calc R . . F1 F 0.0101(6) 0.7363(3) 0.2328(4) 0.0967(16) Uani 1 1 d . . . F2 F 0.0989(4) 0.8729(5) 0.3779(3) 0.0932(14) Uani 1 1 d U . . F3 F 0.0389(3) 1.0182(2) 0.3228(2) 0.0555(8) Uani 1 1 d . . . F4 F -0.0454(6) 0.8788(4) 0.1802(3) 0.0935(14) Uani 1 1 d . . . F5 F 0.1943(5) 0.8858(4) 0.2650(4) 0.0889(14) Uani 1 1 d U . . F6 F -0.1365(3) 0.8680(3) 0.2942(2) 0.0531(7) Uani 1 1 d . . . N1 N 0.8331(3) 0.5205(3) 0.35642(19) 0.0198(6) Uani 1 1 d . . . N2 N 0.7642(3) 0.2960(3) 0.33149(19) 0.0201(6) Uani 1 1 d . . . N3 N 0.7497(3) 0.1352(3) 0.1618(2) 0.0218(6) Uani 1 1 d . . . N4 N 0.8477(3) 0.2276(3) 0.0540(2) 0.0211(6) Uani 1 1 d . . . N5 N 0.7454(3) 0.4348(2) 0.06553(19) 0.0173(5) Uani 1 1 d . . . N6 N 0.5989(3) 0.5269(2) 0.19452(19) 0.0175(5) Uani 1 1 d . . . N7 N 1.0902(3) 0.4138(3) 0.25555(19) 0.0202(6) Uani 1 1 d . . . N8 N 0.4319(3) 0.2550(2) 0.1191(2) 0.0196(6) Uani 1 1 d . . . N9 N 0.5899(4) 1.0210(3) 0.8433(2) 0.0352(8) Uani 1 1 d . . . O1 O 1.0231(3) 0.3251(2) 0.26121(17) 0.0219(5) Uani 1 1 d . . . O2 O 1.0060(3) 0.4671(2) 0.21154(17) 0.0219(5) Uani 1 1 d . . . O3 O 1.2288(3) 0.4475(3) 0.29222(18) 0.0287(6) Uani 1 1 d . . . O4 O 0.5016(3) 0.2995(2) 0.20605(16) 0.0208(5) Uani 1 1 d . . . O5 O 0.5148(3) 0.2501(2) 0.06475(17) 0.0224(5) Uani 1 1 d . . . O6 O 0.2929(3) 0.2201(2) 0.09034(19) 0.0268(5) Uani 1 1 d . . . P1 P 0.03201(15) 0.87913(10) 0.28237(9) 0.0398(3) Uani 1 1 d . . . Tb1 Tb 0.757138(16) 0.351587(13) 0.191055(10) 0.01511(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0224(17) 0.0268(18) 0.0203(17) 0.0054(14) 0.0067(13) 0.0022(14) C2 0.0291(19) 0.0247(18) 0.029(2) 0.0000(16) 0.0102(16) -0.0035(15) C3 0.040(2) 0.036(2) 0.0235(19) -0.0039(17) 0.0139(17) -0.0020(18) C4 0.031(2) 0.038(2) 0.0189(17) 0.0054(16) 0.0093(15) -0.0003(16) C5 0.0183(16) 0.0302(18) 0.0151(15) 0.0077(14) 0.0035(12) 0.0035(13) C6 0.0194(16) 0.0305(18) 0.0165(16) 0.0103(14) 0.0040(13) 0.0051(13) C7 0.033(2) 0.043(2) 0.0206(18) 0.0149(17) 0.0104(15) 0.0041(17) C8 0.040(2) 0.048(3) 0.028(2) 0.0243(19) 0.0117(17) 0.0041(19) C9 0.032(2) 0.037(2) 0.033(2) 0.0226(18) 0.0088(16) 0.0044(16) C10 0.0212(17) 0.0275(17) 0.0234(17) 0.0135(14) 0.0039(14) 0.0052(13) C11 0.0253(17) 0.0225(17) 0.0256(18) 0.0120(15) 0.0037(14) 0.0051(13) C12 0.037(2) 0.0175(16) 0.0206(17) 0.0035(14) 0.0045(15) 0.0077(14) C13 0.0320(19) 0.0235(18) 0.0203(17) 0.0047(14) 0.0081(14) 0.0143(15) C14 0.0195(16) 0.0281(18) 0.0160(15) 0.0037(14) 0.0055(13) 0.0050(13) C15 0.0164(15) 0.0284(18) 0.0149(15) 0.0070(14) 0.0041(12) 0.0021(13) C16 0.0187(16) 0.038(2) 0.0182(16) 0.0120(15) 0.0054(13) 0.0025(14) C17 0.0195(16) 0.038(2) 0.0218(17) 0.0182(16) 0.0044(13) 0.0009(14) C18 0.0169(15) 0.0295(18) 0.0255(17) 0.0160(15) 0.0042(13) 0.0029(13) C19 0.0130(14) 0.0242(16) 0.0170(15) 0.0090(13) 0.0013(12) 0.0023(12) C20 0.0158(15) 0.0200(16) 0.0175(15) 0.0073(13) 0.0025(12) 0.0011(12) C21 0.0212(17) 0.0231(17) 0.0285(18) 0.0136(15) 0.0059(14) 0.0043(13) C22 0.0264(18) 0.0218(17) 0.033(2) 0.0100(15) 0.0076(15) 0.0095(14) C23 0.0220(17) 0.0284(18) 0.0234(17) 0.0069(15) 0.0095(14) 0.0085(14) C24 0.0195(16) 0.0227(16) 0.0175(15) 0.0065(13) 0.0053(12) 0.0037(13) C25 0.0282(19) 0.032(2) 0.031(2) 0.0193(17) 0.0071(16) 0.0023(15) C26 0.044(2) 0.036(2) 0.051(3) 0.023(2) 0.027(2) 0.0121(19) F1 0.141(4) 0.0397(18) 0.144(4) 0.035(2) 0.098(4) 0.034(2) F2 0.058(2) 0.161(4) 0.094(3) 0.096(3) 0.006(2) 0.013(2) F3 0.0469(16) 0.0277(13) 0.090(2) 0.0150(14) 0.0293(16) 0.0043(11) F4 0.144(4) 0.097(3) 0.052(2) 0.033(2) 0.042(2) 0.046(3) F5 0.084(3) 0.084(2) 0.172(4) 0.090(3) 0.094(3) 0.052(2) F6 0.0465(16) 0.0428(16) 0.068(2) 0.0180(15) 0.0183(15) -0.0013(13) N1 0.0187(13) 0.0233(14) 0.0148(13) 0.0053(11) 0.0037(11) 0.0033(11) N2 0.0175(13) 0.0259(15) 0.0165(13) 0.0088(12) 0.0032(11) 0.0037(11) N3 0.0242(15) 0.0195(14) 0.0202(14) 0.0069(12) 0.0050(11) 0.0053(11) N4 0.0209(14) 0.0216(14) 0.0178(14) 0.0046(11) 0.0047(11) 0.0065(11) N5 0.0162(13) 0.0211(14) 0.0140(13) 0.0068(11) 0.0033(10) 0.0031(10) N6 0.0168(13) 0.0187(13) 0.0161(13) 0.0061(11) 0.0041(10) 0.0025(10) N7 0.0192(14) 0.0265(15) 0.0139(13) 0.0052(12) 0.0070(11) 0.0037(11) N8 0.0217(14) 0.0156(13) 0.0210(14) 0.0082(11) 0.0036(11) 0.0033(11) N9 0.0379(19) 0.0348(19) 0.0301(18) 0.0110(16) 0.0077(15) 0.0007(15) O1 0.0220(12) 0.0243(12) 0.0208(12) 0.0101(10) 0.0064(10) 0.0040(9) O2 0.0226(12) 0.0256(12) 0.0195(12) 0.0104(10) 0.0066(10) 0.0045(10) O3 0.0167(12) 0.0417(16) 0.0251(13) 0.0111(12) 0.0051(10) -0.0001(11) O4 0.0226(12) 0.0218(12) 0.0180(11) 0.0081(10) 0.0050(9) 0.0024(9) O5 0.0234(12) 0.0264(13) 0.0186(12) 0.0097(10) 0.0065(10) 0.0054(10) O6 0.0185(12) 0.0259(13) 0.0330(14) 0.0123(11) 0.0015(10) -0.0018(10) P1 0.0541(7) 0.0298(5) 0.0568(7) 0.0257(5) 0.0370(6) 0.0207(5) Tb1 0.01638(9) 0.01666(9) 0.01216(8) 0.00530(6) 0.00419(6) 0.00367(6) _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 C1 N1 1.342(5) . ? C1 C2 1.381(5) . ? C1 H1 0.9500 . ? C2 C3 1.381(6) . ? C2 H2 0.9500 . ? C3 C4 1.377(6) . ? C3 H3 0.9500 . ? C4 C5 1.393(5) . ? C4 H4 0.9500 . ? C5 N1 1.358(4) . ? C5 C6 1.478(5) . ? C6 N2 1.341(4) . ? C6 C7 1.407(5) . ? C7 C8 1.373(6) . ? C7 H7 0.9500 . ? C8 C9 1.391(6) . ? C8 H8 0.9500 . ? C9 C10 1.392(5) . ? C9 H9 0.9500 . ? C10 N2 1.348(5) . ? C10 C11 1.468(5) . ? C11 N3 1.266(5) . ? C11 H11 0.9500 . ? C12 N3 1.467(4) . ? C12 C13 1.520(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N4 1.465(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 N4 1.270(5) . ? C14 C15 1.470(5) . ? C14 H14 0.9500 . ? C15 N5 1.353(4) . ? C15 C16 1.385(5) . ? C16 C17 1.387(6) . ? C16 H16 0.9500 . ? C17 C18 1.382(5) . ? C17 H17 0.9500 . ? C18 C19 1.400(5) . ? C18 H18 0.9500 . ? C19 N5 1.336(4) . ? C19 C20 1.484(5) . ? C20 N6 1.349(4) . ? C20 C21 1.391(5) . ? C21 C22 1.383(5) . ? C21 H21 0.9500 . ? C22 C23 1.373(5) . ? C22 H22 0.9500 . ? C23 C24 1.388(5) . ? C23 H23 0.9500 . ? C24 N6 1.343(4) . ? C24 H24 0.9500 . ? C25 N9 1.140(5) . ? C25 C26 1.455(6) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? F1 P1 1.609(4) . ? F2 P1 1.541(4) . ? F3 P1 1.570(3) . ? F4 P1 1.623(4) . ? F5 P1 1.562(3) . ? F6 P1 1.586(3) . ? N1 Tb1 2.596(3) . ? N2 Tb1 2.587(3) . ? N3 Tb1 2.506(3) . ? N4 Tb1 2.510(3) . ? N5 Tb1 2.569(3) . ? N6 Tb1 2.601(3) . ? N7 O3 1.227(4) . ? N7 O2 1.272(4) . ? N7 O1 1.272(4) . ? N8 O6 1.226(4) . ? N8 O5 1.272(4) . ? N8 O4 1.277(4) . ? O1 Tb1 2.474(2) . ? O2 Tb1 2.500(2) . ? O4 Tb1 2.466(2) . ? O5 Tb1 2.494(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 N1 C1 C2 123.2(3) . . ? N1 C1 H1 118.4 . . ? C2 C1 H1 118.4 . . ? C3 C2 C1 118.5(4) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C4 C3 C2 119.5(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 119.1(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? N1 C5 C4 121.7(3) . . ? N1 C5 C6 115.9(3) . . ? C4 C5 C6 122.3(3) . . ? N2 C6 C7 121.1(3) . . ? N2 C6 C5 115.8(3) . . ? C7 C6 C5 123.0(3) . . ? C8 C7 C6 119.6(4) . . ? C8 C7 H7 120.2 . . ? C6 C7 H7 120.2 . . ? C7 C8 C9 119.5(4) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C8 C9 C10 117.9(4) . . ? C8 C9 H9 121.0 . . ? C10 C9 H9 121.0 . . ? N2 C10 C9 123.0(4) . . ? N2 C10 C11 115.6(3) . . ? C9 C10 C11 121.4(4) . . ? N3 C11 C10 119.2(3) . . ? N3 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? N3 C12 C13 107.1(3) . . ? N3 C12 H12A 110.3 . . ? C13 C12 H12A 110.3 . . ? N3 C12 H12B 110.3 . . ? C13 C12 H12B 110.3 . . ? H12A C12 H12B 108.6 . . ? N4 C13 C12 107.4(3) . . ? N4 C13 H13A 110.2 . . ? C12 C13 H13A 110.2 . . ? N4 C13 H13B 110.2 . . ? C12 C13 H13B 110.2 . . ? H13A C13 H13B 108.5 . . ? N4 C14 C15 119.2(3) . . ? N4 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? N5 C15 C16 123.0(3) . . ? N5 C15 C14 115.5(3) . . ? C16 C15 C14 121.5(3) . . ? C15 C16 C17 118.5(3) . . ? C15 C16 H16 120.8 . . ? C17 C16 H16 120.8 . . ? C18 C17 C16 118.9(3) . . ? C18 C17 H17 120.6 . . ? C16 C17 H17 120.6 . . ? C17 C18 C19 119.5(3) . . ? C17 C18 H18 120.3 . . ? C19 C18 H18 120.3 . . ? N5 C19 C18 121.8(3) . . ? N5 C19 C20 115.8(3) . . ? C18 C19 C20 122.4(3) . . ? N6 C20 C21 121.9(3) . . ? N6 C20 C19 115.7(3) . . ? C21 C20 C19 122.3(3) . . ? C22 C21 C20 119.2(3) . . ? C22 C21 H21 120.4 . . ? C20 C21 H21 120.4 . . ? C23 C22 C21 119.2(3) . . ? C23 C22 H22 120.4 . . ? C21 C22 H22 120.4 . . ? C22 C23 C24 118.7(3) . . ? C22 C23 H23 120.7 . . ? C24 C23 H23 120.7 . . ? N6 C24 C23 123.1(3) . . ? N6 C24 H24 118.5 . . ? C23 C24 H24 118.5 . . ? N9 C25 C26 179.1(5) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C1 N1 C5 117.9(3) . . ? C1 N1 Tb1 120.0(2) . . ? C5 N1 Tb1 120.9(2) . . ? C6 N2 C10 118.8(3) . . ? C6 N2 Tb1 122.2(2) . . ? C10 N2 Tb1 118.4(2) . . ? C11 N3 C12 119.1(3) . . ? C11 N3 Tb1 122.8(2) . . ? C12 N3 Tb1 118.1(2) . . ? C14 N4 C13 119.3(3) . . ? C14 N4 Tb1 122.2(2) . . ? C13 N4 Tb1 118.4(2) . . ? C19 N5 C15 118.3(3) . . ? C19 N5 Tb1 122.3(2) . . ? C15 N5 Tb1 118.6(2) . . ? C24 N6 C20 117.9(3) . . ? C24 N6 Tb1 120.5(2) . . ? C20 N6 Tb1 120.7(2) . . ? O3 N7 O2 121.7(3) . . ? O3 N7 O1 121.6(3) . . ? O2 N7 O1 116.7(3) . . ? O6 N8 O5 122.4(3) . . ? O6 N8 O4 121.5(3) . . ? O5 N8 O4 116.1(3) . . ? N7 O1 Tb1 96.21(18) . . ? N7 O2 Tb1 95.00(18) . . ? N8 O4 Tb1 96.62(18) . . ? N8 O5 Tb1 95.46(18) . . ? F2 P1 F5 92.9(2) . . ? F2 P1 F3 94.8(3) . . ? F5 P1 F3 92.22(19) . . ? F2 P1 F6 89.5(2) . . ? F5 P1 F6 176.9(3) . . ? F3 P1 F6 89.46(16) . . ? F2 P1 F1 90.2(3) . . ? F5 P1 F1 90.4(2) . . ? F3 P1 F1 174.3(3) . . ? F6 P1 F1 87.7(2) . . ? F2 P1 F4 176.7(3) . . ? F5 P1 F4 89.1(3) . . ? F3 P1 F4 87.8(2) . . ? F6 P1 F4 88.4(2) . . ? F1 P1 F4 87.2(3) . . ? O4 Tb1 O1 133.83(8) . . ? O4 Tb1 O5 51.71(8) . . ? O1 Tb1 O5 143.91(8) . . ? O4 Tb1 O2 161.76(8) . . ? O1 Tb1 O2 51.61(8) . . ? O5 Tb1 O2 137.90(8) . . ? O4 Tb1 N3 76.75(9) . . ? O1 Tb1 N3 73.99(9) . . ? O5 Tb1 N3 74.25(9) . . ? O2 Tb1 N3 118.98(9) . . ? O4 Tb1 N4 121.47(9) . . ? O1 Tb1 N4 75.89(9) . . ? O5 Tb1 N4 75.50(9) . . ? O2 Tb1 N4 75.79(9) . . ? N3 Tb1 N4 65.02(10) . . ? O4 Tb1 N5 113.75(8) . . ? O1 Tb1 N5 112.17(8) . . ? O5 Tb1 N5 73.29(8) . . ? O2 Tb1 N5 66.59(8) . . ? N3 Tb1 N5 124.23(9) . . ? N4 Tb1 N5 63.66(9) . . ? O4 Tb1 N2 65.17(8) . . ? O1 Tb1 N2 69.97(8) . . ? O5 Tb1 N2 109.58(8) . . ? O2 Tb1 N2 111.86(8) . . ? N3 Tb1 N2 63.31(9) . . ? N4 Tb1 N2 123.71(9) . . ? N5 Tb1 N2 172.35(9) . . ? O4 Tb1 N1 91.59(8) . . ? O1 Tb1 N1 76.17(8) . . ? O5 Tb1 N1 137.09(8) . . ? O2 Tb1 N1 72.24(8) . . ? N3 Tb1 N1 123.42(9) . . ? N4 Tb1 N1 146.33(9) . . ? N5 Tb1 N1 111.27(9) . . ? N2 Tb1 N1 61.64(9) . . ? O4 Tb1 N6 71.97(8) . . ? O1 Tb1 N6 137.63(8) . . ? O5 Tb1 N6 77.51(8) . . ? O2 Tb1 N6 93.88(8) . . ? N3 Tb1 N6 146.68(9) . . ? N4 Tb1 N6 123.79(9) . . ? N5 Tb1 N6 61.68(9) . . ? N2 Tb1 N6 111.54(9) . . ? N1 Tb1 N6 69.31(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.7(6) . . . . ? C1 C2 C3 C4 0.1(6) . . . . ? C2 C3 C4 C5 0.0(6) . . . . ? C3 C4 C5 N1 -0.9(6) . . . . ? C3 C4 C5 C6 176.9(4) . . . . ? N1 C5 C6 N2 -1.5(4) . . . . ? C4 C5 C6 N2 -179.5(3) . . . . ? N1 C5 C6 C7 175.7(3) . . . . ? C4 C5 C6 C7 -2.2(5) . . . . ? N2 C6 C7 C8 2.6(6) . . . . ? C5 C6 C7 C8 -174.5(4) . . . . ? C6 C7 C8 C9 -0.6(6) . . . . ? C7 C8 C9 C10 -1.4(6) . . . . ? C8 C9 C10 N2 1.6(6) . . . . ? C8 C9 C10 C11 -179.4(4) . . . . ? N2 C10 C11 N3 -6.9(5) . . . . ? C9 C10 C11 N3 174.1(4) . . . . ? N3 C12 C13 N4 -53.1(4) . . . . ? N4 C14 C15 N5 -8.5(5) . . . . ? N4 C14 C15 C16 172.6(3) . . . . ? N5 C15 C16 C17 2.1(5) . . . . ? C14 C15 C16 C17 -179.1(3) . . . . ? C15 C16 C17 C18 -1.8(5) . . . . ? C16 C17 C18 C19 -0.7(5) . . . . ? C17 C18 C19 N5 3.0(5) . . . . ? C17 C18 C19 C20 -174.6(3) . . . . ? N5 C19 C20 N6 -0.1(4) . . . . ? C18 C19 C20 N6 177.6(3) . . . . ? N5 C19 C20 C21 -178.2(3) . . . . ? C18 C19 C20 C21 -0.5(5) . . . . ? N6 C20 C21 C22 -1.2(5) . . . . ? C19 C20 C21 C22 176.7(3) . . . . ? C20 C21 C22 C23 -0.8(5) . . . . ? C21 C22 C23 C24 1.6(6) . . . . ? C22 C23 C24 N6 -0.5(5) . . . . ? C2 C1 N1 C5 -1.5(5) . . . . ? C2 C1 N1 Tb1 166.1(3) . . . . ? C4 C5 N1 C1 1.6(5) . . . . ? C6 C5 N1 C1 -176.4(3) . . . . ? C4 C5 N1 Tb1 -165.9(3) . . . . ? C6 C5 N1 Tb1 16.2(4) . . . . ? C7 C6 N2 C10 -2.4(5) . . . . ? C5 C6 N2 C10 174.9(3) . . . . ? C7 C6 N2 Tb1 168.7(3) . . . . ? C5 C6 N2 Tb1 -14.0(4) . . . . ? C9 C10 N2 C6 0.3(5) . . . . ? C11 C10 N2 C6 -178.8(3) . . . . ? C9 C10 N2 Tb1 -171.1(3) . . . . ? C11 C10 N2 Tb1 9.8(4) . . . . ? C10 C11 N3 C12 177.5(3) . . . . ? C10 C11 N3 Tb1 0.2(5) . . . . ? C13 C12 N3 C11 -133.4(3) . . . . ? C13 C12 N3 Tb1 44.0(3) . . . . ? C15 C14 N4 C13 176.4(3) . . . . ? C15 C14 N4 Tb1 1.1(4) . . . . ? C12 C13 N4 C14 -133.7(3) . . . . ? C12 C13 N4 Tb1 41.8(3) . . . . ? C18 C19 N5 C15 -2.7(5) . . . . ? C20 C19 N5 C15 175.0(3) . . . . ? C18 C19 N5 Tb1 166.6(2) . . . . ? C20 C19 N5 Tb1 -15.6(4) . . . . ? C16 C15 N5 C19 0.2(5) . . . . ? C14 C15 N5 C19 -178.7(3) . . . . ? C16 C15 N5 Tb1 -169.6(3) . . . . ? C14 C15 N5 Tb1 11.5(4) . . . . ? C23 C24 N6 C20 -1.5(5) . . . . ? C23 C24 N6 Tb1 167.5(3) . . . . ? C21 C20 N6 C24 2.4(5) . . . . ? C19 C20 N6 C24 -175.7(3) . . . . ? C21 C20 N6 Tb1 -166.5(2) . . . . ? C19 C20 N6 Tb1 15.4(4) . . . . ? O3 N7 O1 Tb1 171.7(3) . . . . ? O2 N7 O1 Tb1 -7.0(3) . . . . ? O3 N7 O2 Tb1 -171.8(3) . . . . ? O1 N7 O2 Tb1 6.9(3) . . . . ? O6 N8 O4 Tb1 -176.3(3) . . . . ? O5 N8 O4 Tb1 3.1(3) . . . . ? O6 N8 O5 Tb1 176.3(3) . . . . ? O4 N8 O5 Tb1 -3.1(3) . . . . ? N8 O4 Tb1 O1 -133.82(17) . . . . ? N8 O4 Tb1 O5 -1.81(16) . . . . ? N8 O4 Tb1 O2 126.8(3) . . . . ? N8 O4 Tb1 N3 -82.05(18) . . . . ? N8 O4 Tb1 N4 -32.8(2) . . . . ? N8 O4 Tb1 N5 39.8(2) . . . . ? N8 O4 Tb1 N2 -148.5(2) . . . . ? N8 O4 Tb1 N1 153.93(18) . . . . ? N8 O4 Tb1 N6 86.31(18) . . . . ? N7 O1 Tb1 O4 -152.72(16) . . . . ? N7 O1 Tb1 O5 125.40(18) . . . . ? N7 O1 Tb1 O2 4.07(16) . . . . ? N7 O1 Tb1 N3 154.58(19) . . . . ? N7 O1 Tb1 N4 86.96(18) . . . . ? N7 O1 Tb1 N5 33.6(2) . . . . ? N7 O1 Tb1 N2 -138.55(19) . . . . ? N7 O1 Tb1 N1 -74.07(18) . . . . ? N7 O1 Tb1 N6 -38.2(2) . . . . ? N8 O5 Tb1 O4 1.81(16) . . . . ? N8 O5 Tb1 O1 116.32(19) . . . . ? N8 O5 Tb1 O2 -156.80(16) . . . . ? N8 O5 Tb1 N3 87.18(19) . . . . ? N8 O5 Tb1 N4 154.83(19) . . . . ? N8 O5 Tb1 N5 -138.80(19) . . . . ? N8 O5 Tb1 N2 33.7(2) . . . . ? N8 O5 Tb1 N1 -35.3(2) . . . . ? N8 O5 Tb1 N6 -74.95(18) . . . . ? N7 O2 Tb1 O4 110.7(3) . . . . ? N7 O2 Tb1 O1 -4.06(16) . . . . ? N7 O2 Tb1 O5 -135.43(17) . . . . ? N7 O2 Tb1 N3 -36.8(2) . . . . ? N7 O2 Tb1 N4 -87.15(18) . . . . ? N7 O2 Tb1 N5 -154.2(2) . . . . ? N7 O2 Tb1 N2 33.9(2) . . . . ? N7 O2 Tb1 N1 82.13(18) . . . . ? N7 O2 Tb1 N6 148.94(18) . . . . ? C11 N3 Tb1 O4 -65.2(3) . . . . ? C12 N3 Tb1 O4 117.4(3) . . . . ? C11 N3 Tb1 O1 78.6(3) . . . . ? C12 N3 Tb1 O1 -98.7(3) . . . . ? C11 N3 Tb1 O5 -118.7(3) . . . . ? C12 N3 Tb1 O5 63.9(2) . . . . ? C11 N3 Tb1 O2 104.8(3) . . . . ? C12 N3 Tb1 O2 -72.5(3) . . . . ? C11 N3 Tb1 N4 160.2(3) . . . . ? C12 N3 Tb1 N4 -17.1(2) . . . . ? C11 N3 Tb1 N5 -175.1(3) . . . . ? C12 N3 Tb1 N5 7.5(3) . . . . ? C11 N3 Tb1 N2 3.4(3) . . . . ? C12 N3 Tb1 N2 -173.9(3) . . . . ? C11 N3 Tb1 N1 17.8(3) . . . . ? C12 N3 Tb1 N1 -159.5(2) . . . . ? C11 N3 Tb1 N6 -85.7(3) . . . . ? C12 N3 Tb1 N6 97.0(3) . . . . ? C14 N4 Tb1 O4 106.3(3) . . . . ? C13 N4 Tb1 O4 -69.0(3) . . . . ? C14 N4 Tb1 O1 -120.6(3) . . . . ? C13 N4 Tb1 O1 64.1(2) . . . . ? C14 N4 Tb1 O5 81.6(3) . . . . ? C13 N4 Tb1 O5 -93.7(2) . . . . ? C14 N4 Tb1 O2 -67.3(3) . . . . ? C13 N4 Tb1 O2 117.4(3) . . . . ? C14 N4 Tb1 N3 160.7(3) . . . . ? C13 N4 Tb1 N3 -14.6(2) . . . . ? C14 N4 Tb1 N5 3.3(3) . . . . ? C13 N4 Tb1 N5 -172.0(3) . . . . ? C14 N4 Tb1 N2 -174.3(3) . . . . ? C13 N4 Tb1 N2 10.4(3) . . . . ? C14 N4 Tb1 N1 -85.9(3) . . . . ? C13 N4 Tb1 N1 98.8(3) . . . . ? C14 N4 Tb1 N6 17.8(3) . . . . ? C13 N4 Tb1 N6 -157.5(2) . . . . ? C19 N5 Tb1 O4 68.0(3) . . . . ? C15 N5 Tb1 O4 -122.6(2) . . . . ? C19 N5 Tb1 O1 -116.9(2) . . . . ? C15 N5 Tb1 O1 52.4(3) . . . . ? C19 N5 Tb1 O5 101.0(2) . . . . ? C15 N5 Tb1 O5 -89.6(2) . . . . ? C19 N5 Tb1 O2 -92.1(2) . . . . ? C15 N5 Tb1 O2 77.3(2) . . . . ? C19 N5 Tb1 N3 157.8(2) . . . . ? C15 N5 Tb1 N3 -32.8(3) . . . . ? C19 N5 Tb1 N4 -177.2(3) . . . . ? C15 N5 Tb1 N4 -7.9(2) . . . . ? C19 N5 Tb1 N1 -33.7(3) . . . . ? C15 N5 Tb1 N1 135.6(2) . . . . ? C19 N5 Tb1 N6 16.4(2) . . . . ? C15 N5 Tb1 N6 -174.2(3) . . . . ? C6 N2 Tb1 O4 -90.9(3) . . . . ? C10 N2 Tb1 O4 80.1(2) . . . . ? C6 N2 Tb1 O1 100.3(3) . . . . ? C10 N2 Tb1 O1 -88.6(2) . . . . ? C6 N2 Tb1 O5 -118.2(3) . . . . ? C10 N2 Tb1 O5 52.9(3) . . . . ? C6 N2 Tb1 O2 69.4(3) . . . . ? C10 N2 Tb1 O2 -119.5(2) . . . . ? C6 N2 Tb1 N3 -178.1(3) . . . . ? C10 N2 Tb1 N3 -7.0(2) . . . . ? C6 N2 Tb1 N4 156.6(2) . . . . ? C10 N2 Tb1 N4 -32.4(3) . . . . ? C6 N2 Tb1 N1 15.6(2) . . . . ? C10 N2 Tb1 N1 -173.3(3) . . . . ? C6 N2 Tb1 N6 -34.3(3) . . . . ? C10 N2 Tb1 N6 136.8(2) . . . . ? C1 N1 Tb1 O4 -122.8(3) . . . . ? C5 N1 Tb1 O4 44.4(3) . . . . ? C1 N1 Tb1 O1 102.2(3) . . . . ? C5 N1 Tb1 O1 -90.6(3) . . . . ? C1 N1 Tb1 O5 -94.5(3) . . . . ? C5 N1 Tb1 O5 72.6(3) . . . . ? C1 N1 Tb1 O2 48.6(2) . . . . ? C5 N1 Tb1 O2 -144.3(3) . . . . ? C1 N1 Tb1 N3 162.0(2) . . . . ? C5 N1 Tb1 N3 -30.8(3) . . . . ? C1 N1 Tb1 N4 67.6(3) . . . . ? C5 N1 Tb1 N4 -125.3(3) . . . . ? C1 N1 Tb1 N5 -6.5(3) . . . . ? C5 N1 Tb1 N5 160.7(2) . . . . ? C1 N1 Tb1 N2 176.7(3) . . . . ? C5 N1 Tb1 N2 -16.2(2) . . . . ? C1 N1 Tb1 N6 -52.8(2) . . . . ? C5 N1 Tb1 N6 114.4(3) . . . . ? C24 N6 Tb1 O4 44.2(2) . . . . ? C20 N6 Tb1 O4 -147.2(3) . . . . ? C24 N6 Tb1 O1 -92.2(3) . . . . ? C20 N6 Tb1 O1 76.5(3) . . . . ? C24 N6 Tb1 O5 97.7(2) . . . . ? C20 N6 Tb1 O5 -93.7(2) . . . . ? C24 N6 Tb1 O2 -124.0(2) . . . . ? C20 N6 Tb1 O2 44.6(2) . . . . ? C24 N6 Tb1 N3 65.1(3) . . . . ? C20 N6 Tb1 N3 -126.2(2) . . . . ? C24 N6 Tb1 N4 160.5(2) . . . . ? C20 N6 Tb1 N4 -30.9(3) . . . . ? C24 N6 Tb1 N5 175.2(3) . . . . ? C20 N6 Tb1 N5 -16.1(2) . . . . ? C24 N6 Tb1 N2 -8.7(3) . . . . ? C20 N6 Tb1 N2 159.9(2) . . . . ? C24 N6 Tb1 N1 -54.7(2) . . . . ? C20 N6 Tb1 N1 114.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 2.870 _refine_diff_density_min -1.409 _refine_diff_density_rms 0.125 _database_code_depnum_ccdc_archive 'CCDC 919431'