# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Markus Albrecht' _publ_contact_author_email MARKUS.ALBRECHT@OC.RWTH-AACHEN.DE _publ_section_title ; 1:1 Versus 2:1 coordination of pentadentate hydrazone-type ligands to lanthanide(III) ions. Formation of cationic as well as dicationic complexes. ; loop_ _publ_author_name 'Markus Albrecht' 'Anna Exarchos' 'Roland Frohlich' 'Philipp Nachev' 'Yeni Yulia' # Attachment 'Copy of fro4482.cif' data_fro4482 _database_code_depnum_ccdc_archive 'CCDC 728920' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H31 N10 Nd O13' _chemical_formula_weight 847.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 10.1311(1) _cell_length_b 15.0971(2) _cell_length_c 22.9512(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.337(1) _cell_angle_gamma 90.00 _cell_volume 3441.90(7) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3004 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 28.28 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.636 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1708 _exptl_absorpt_coefficient_mu 1.586 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6476 _exptl_absorpt_correction_T_max 0.7421 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9744 _diffrn_reflns_av_R_equivalents 0.022 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4227 _reflns_number_gt 3906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrcik, 1997)' _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^)+(0.0308P)^2^+2.9820P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at N3 from difmap, others geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4227 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0251 _refine_ls_wR_factor_ref 0.0631 _refine_ls_wR_factor_gt 0.0615 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Nd Nd 0.0000 0.160093(9) 0.2500 0.02394(6) Uani 1 2 d S . . O1 O 0.20593(14) 0.23620(10) 0.31065(7) 0.0328(3) Uani 1 1 d . . . C2 C 0.31058(19) 0.20040(14) 0.33709(9) 0.0261(4) Uani 1 1 d . . . N3 N 0.32659(17) 0.11193(12) 0.33407(8) 0.0291(4) Uani 1 1 d . . . H3 H 0.388(3) 0.0846(17) 0.3550(12) 0.036(7) Uiso 1 1 d . . . N4 N 0.21779(16) 0.06557(11) 0.30355(7) 0.0256(3) Uani 1 1 d . . . C5 C 0.2281(2) -0.01874(13) 0.30346(9) 0.0267(4) Uani 1 1 d . . . H5 H 0.3084 -0.0471 0.3214 0.032 Uiso 1 1 calc R . . C6 C 0.11046(19) -0.06952(13) 0.27450(8) 0.0252(4) Uani 1 1 d . . . N7 N 0.0000 -0.02336(15) 0.2500 0.0242(5) Uani 1 2 d S . . C8 C 0.1152(2) -0.16164(13) 0.27475(10) 0.0280(4) Uani 1 1 d . . . H8 H 0.1950 -0.1915 0.2914 0.034 Uiso 1 1 calc R . . C9 C 0.0000 -0.2087(2) 0.2500 0.0334(7) Uani 1 2 d S . . H9 H 0.0000 -0.2710 0.2500 0.040 Uiso 1 2 calc SR . . N11 N 0.0000 0.35630(19) 0.2500 0.0427(7) Uani 1 2 d S . . O12 O 0.04702(16) 0.31281(11) 0.21152(7) 0.0356(3) Uani 1 1 d . . . O13 O 0.0000 0.43769(19) 0.2500 0.0962(14) Uani 1 2 d S . . N15 N -0.1118(2) 0.12366(14) 0.36013(9) 0.0386(4) Uani 1 1 d . . . O16 O 0.01254(18) 0.12252(14) 0.35991(8) 0.0468(4) Uani 1 1 d . . . O17 O -0.18824(18) 0.14513(13) 0.31220(8) 0.0460(4) Uani 1 1 d . . . O18 O -0.1543(2) 0.10476(16) 0.40505(9) 0.0669(6) Uani 1 1 d . . . C21 C 0.4225(2) 0.25240(14) 0.37284(9) 0.0271(4) Uani 1 1 d . . . C22 C 0.3982(2) 0.34166(14) 0.38248(11) 0.0338(5) Uani 1 1 d . . . H22 H 0.3127 0.3660 0.3680 0.041 Uiso 1 1 calc R . . C23 C 0.5006(3) 0.39427(17) 0.41343(12) 0.0456(6) Uani 1 1 d . . . H23 H 0.4845 0.4544 0.4203 0.055 Uiso 1 1 calc R . . C24 C 0.6269(3) 0.35783(19) 0.43432(13) 0.0486(7) Uani 1 1 d . . . H24 H 0.6963 0.3935 0.4553 0.058 Uiso 1 1 calc R . . C25 C 0.6511(2) 0.26993(17) 0.42453(11) 0.0415(6) Uani 1 1 d . . . H25 H 0.7370 0.2459 0.4388 0.050 Uiso 1 1 calc R . . C26 C 0.5496(2) 0.21685(15) 0.39382(9) 0.0315(4) Uani 1 1 d . . . H26 H 0.5664 0.1568 0.3871 0.038 Uiso 1 1 calc R . . O31 O 0.4792(2) -0.00345(13) 0.41106(10) 0.0655(6) Uani 1 1 d . . . C32 C 0.5859(3) -0.01939(18) 0.44456(12) 0.0512(7) Uani 1 1 d . . . H32 H 0.6439 0.0286 0.4567 0.061 Uiso 1 1 calc R . . N33 N 0.6263(2) -0.09837(14) 0.46507(9) 0.0404(5) Uani 1 1 d . . . C34 C 0.7493(3) -0.1099(2) 0.50954(14) 0.0611(8) Uani 1 1 d . . . H34A H 0.7968 -0.0539 0.5160 0.092 Uiso 1 1 calc R . . H34B H 0.8063 -0.1535 0.4957 0.092 Uiso 1 1 calc R . . H34C H 0.7267 -0.1300 0.5465 0.092 Uiso 1 1 calc R . . C35 C 0.5464(4) -0.1758(2) 0.44579(17) 0.0666(9) Uani 1 1 d . . . H35A H 0.4660 -0.1585 0.4177 0.100 Uiso 1 1 calc R . . H35B H 0.5210 -0.2042 0.4799 0.100 Uiso 1 1 calc R . . H35C H 0.5985 -0.2168 0.4268 0.100 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Nd 0.01753(8) 0.02441(9) 0.02796(9) 0.000 -0.00021(5) 0.000 O1 0.0220(7) 0.0290(7) 0.0422(9) 0.0011(6) -0.0060(6) 0.0014(6) C2 0.0208(9) 0.0301(10) 0.0264(9) 0.0015(8) 0.0024(7) -0.0001(8) N3 0.0193(8) 0.0275(9) 0.0350(9) -0.0003(7) -0.0079(7) 0.0022(7) N4 0.0188(8) 0.0288(9) 0.0272(8) -0.0010(6) -0.0006(6) -0.0007(7) C5 0.0218(9) 0.0261(9) 0.0297(10) -0.0006(8) -0.0011(7) 0.0041(8) C6 0.0228(9) 0.0278(10) 0.0244(9) -0.0010(7) 0.0034(7) 0.0025(8) N7 0.0230(11) 0.0238(11) 0.0247(11) 0.000 0.0023(9) 0.000 C8 0.0286(11) 0.0253(10) 0.0302(10) 0.0014(7) 0.0061(8) 0.0057(8) C9 0.0379(17) 0.0281(15) 0.0364(16) 0.000 0.0131(13) 0.000 N11 0.0297(15) 0.0275(14) 0.071(2) 0.000 0.0105(14) 0.000 O12 0.0260(8) 0.0337(8) 0.0457(9) 0.0043(7) 0.0032(7) -0.0013(7) O13 0.105(3) 0.0287(15) 0.176(4) 0.000 0.079(3) 0.000 N15 0.0464(12) 0.0347(10) 0.0383(11) 0.0020(8) 0.0169(9) 0.0084(10) O16 0.0379(9) 0.0647(12) 0.0381(9) 0.0077(8) 0.0082(7) 0.0124(9) O17 0.0328(9) 0.0630(12) 0.0417(10) 0.0040(8) 0.0064(7) -0.0016(8) O18 0.0769(15) 0.0802(15) 0.0546(12) 0.0239(11) 0.0398(11) 0.0271(13) C21 0.0251(10) 0.0300(10) 0.0246(9) 0.0023(8) 0.0011(8) -0.0016(8) C22 0.0293(11) 0.0344(12) 0.0355(12) -0.0034(8) 0.0012(9) 0.0026(9) C23 0.0471(14) 0.0332(12) 0.0520(15) -0.0130(11) -0.0009(12) -0.0027(11) C24 0.0395(14) 0.0443(14) 0.0531(16) -0.0138(12) -0.0126(12) -0.0092(12) C25 0.0285(11) 0.0434(13) 0.0452(13) 0.0015(10) -0.0106(10) -0.0014(10) C26 0.0265(10) 0.0302(10) 0.0338(11) 0.0015(8) -0.0039(8) -0.0016(9) O31 0.0624(13) 0.0413(10) 0.0742(14) 0.0076(9) -0.0318(11) 0.0080(10) C32 0.0544(16) 0.0351(13) 0.0531(16) 0.0028(11) -0.0167(12) 0.0026(13) N33 0.0414(11) 0.0385(11) 0.0368(10) 0.0045(8) -0.0033(8) 0.0082(9) C34 0.0527(17) 0.070(2) 0.0522(17) 0.0097(14) -0.0097(13) 0.0226(16) C35 0.073(2) 0.0401(15) 0.078(2) 0.0113(14) -0.0069(18) -0.0013(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Nd O1 2.5434(14) . ? Nd O1 2.5434(14) 2 ? Nd O12 2.5472(16) 2 ? Nd O12 2.5472(16) . ? Nd O16 2.5641(17) . ? Nd O16 2.5641(17) 2 ? Nd O17 2.6070(18) . ? Nd O17 2.6070(18) 2 ? Nd N4 2.7110(16) 2 ? Nd N4 2.7110(16) . ? Nd N7 2.770(2) . ? Nd N11 2.962(3) . ? O1 C2 1.238(2) . ? C2 N3 1.349(3) . ? C2 C21 1.486(3) . ? N3 N4 1.375(2) . ? N3 H3 0.82(3) . ? N4 C5 1.277(3) . ? C5 C6 1.462(3) . ? C5 H5 0.9400 . ? C6 N7 1.344(2) . ? C6 C8 1.392(3) . ? N7 C6 1.344(2) 2 ? C8 C9 1.388(3) . ? C8 H8 0.9400 . ? C9 C8 1.388(3) 2 ? C9 H9 0.9400 . ? N11 O13 1.229(4) . ? N11 O12 1.266(2) 2 ? N11 O12 1.266(2) . ? N15 O18 1.226(3) . ? N15 O17 1.257(3) . ? N15 O16 1.261(3) . ? C21 C26 1.391(3) . ? C21 C22 1.395(3) . ? C22 C23 1.386(3) . ? C22 H22 0.9400 . ? C23 C24 1.389(4) . ? C23 H23 0.9400 . ? C24 C25 1.376(4) . ? C24 H24 0.9400 . ? C25 C26 1.383(3) . ? C25 H25 0.9400 . ? C26 H26 0.9400 . ? O31 C32 1.221(3) . ? C32 N33 1.317(3) . ? C32 H32 0.9400 . ? N33 C35 1.441(4) . ? N33 C34 1.458(3) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 H34C 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C35 H35C 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Nd O1 126.29(7) . 2 ? O1 Nd O12 65.83(5) . 2 ? O1 Nd O12 65.90(5) 2 2 ? O1 Nd O12 65.90(5) . . ? O1 Nd O12 65.83(5) 2 . ? O12 Nd O12 50.31(8) 2 . ? O1 Nd O16 71.63(6) . . ? O1 Nd O16 121.00(5) 2 . ? O12 Nd O16 80.54(6) 2 . ? O12 Nd O16 124.39(6) . . ? O1 Nd O16 121.00(5) . 2 ? O1 Nd O16 71.63(6) 2 2 ? O12 Nd O16 124.39(6) 2 2 ? O12 Nd O16 80.54(6) . 2 ? O16 Nd O16 154.44(9) . 2 ? O1 Nd O17 110.43(6) . . ? O1 Nd O17 74.29(6) 2 . ? O12 Nd O17 71.44(6) 2 . ? O12 Nd O17 118.36(6) . . ? O16 Nd O17 48.87(6) . . ? O16 Nd O17 128.27(6) 2 . ? O1 Nd O17 74.29(6) . 2 ? O1 Nd O17 110.43(6) 2 2 ? O12 Nd O17 118.36(6) 2 2 ? O12 Nd O17 71.44(6) . 2 ? O16 Nd O17 128.27(6) . 2 ? O16 Nd O17 48.87(6) 2 2 ? O17 Nd O17 170.06(9) . 2 ? O1 Nd N4 173.17(5) . 2 ? O1 Nd N4 58.85(5) 2 2 ? O12 Nd N4 116.27(5) 2 2 ? O12 Nd N4 120.68(5) . 2 ? O16 Nd N4 102.01(6) . 2 ? O16 Nd N4 63.83(5) 2 2 ? O17 Nd N4 65.47(6) . 2 ? O17 Nd N4 108.90(5) 2 2 ? O1 Nd N4 58.85(5) . . ? O1 Nd N4 173.17(5) 2 . ? O12 Nd N4 120.68(5) 2 . ? O12 Nd N4 116.27(5) . . ? O16 Nd N4 63.83(5) . . ? O16 Nd N4 102.01(6) 2 . ? O17 Nd N4 108.90(5) . . ? O17 Nd N4 65.47(6) 2 . ? N4 Nd N4 116.48(7) 2 . ? O1 Nd N7 116.86(3) . . ? O1 Nd N7 116.86(3) 2 . ? O12 Nd N7 154.85(4) 2 . ? O12 Nd N7 154.85(4) . . ? O16 Nd N7 77.22(5) . . ? O16 Nd N7 77.22(5) 2 . ? O17 Nd N7 85.03(4) . . ? O17 Nd N7 85.03(4) 2 . ? N4 Nd N7 58.24(4) 2 . ? N4 Nd N7 58.24(4) . . ? O1 Nd N11 63.14(3) . . ? O1 Nd N11 63.14(3) 2 . ? O12 Nd N11 25.15(4) 2 . ? O12 Nd N11 25.15(4) . . ? O16 Nd N11 102.78(5) . . ? O16 Nd N11 102.78(5) 2 . ? O17 Nd N11 94.97(4) . . ? O17 Nd N11 94.97(4) 2 . ? N4 Nd N11 121.76(4) 2 . ? N4 Nd N11 121.76(4) . . ? N7 Nd N11 180.0 . . ? C2 O1 Nd 127.05(13) . . ? O1 C2 N3 120.49(18) . . ? O1 C2 C21 121.80(19) . . ? N3 C2 C21 117.71(17) . . ? C2 N3 N4 115.95(16) . . ? C2 N3 H3 123.7(19) . . ? N4 N3 H3 118.7(19) . . ? C5 N4 N3 116.77(17) . . ? C5 N4 Nd 125.69(13) . . ? N3 N4 Nd 117.54(12) . . ? N4 C5 C6 117.62(18) . . ? N4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? N7 C6 C8 123.0(2) . . ? N7 C6 C5 117.10(18) . . ? C8 C6 C5 119.86(18) . . ? C6 N7 C6 117.6(2) 2 . ? C6 N7 Nd 121.22(12) 2 . ? C6 N7 Nd 121.22(12) . . ? C9 C8 C6 119.0(2) . . ? C9 C8 H8 120.5 . . ? C6 C8 H8 120.5 . . ? C8 C9 C8 118.5(3) . 2 ? C8 C9 H9 120.8 . . ? C8 C9 H9 120.8 2 . ? O13 N11 O12 121.23(13) . 2 ? O13 N11 O12 121.23(13) . . ? O12 N11 O12 117.5(3) 2 . ? O13 N11 Nd 180.0 . . ? O12 N11 Nd 58.77(13) 2 . ? O12 N11 Nd 58.77(13) . . ? N11 O12 Nd 96.08(14) . . ? O18 N15 O17 122.6(2) . . ? O18 N15 O16 121.1(2) . . ? O17 N15 O16 116.35(19) . . ? N15 O16 Nd 98.32(13) . . ? N15 O17 Nd 96.35(13) . . ? C26 C21 C22 119.8(2) . . ? C26 C21 C2 122.75(19) . . ? C22 C21 C2 117.31(19) . . ? C23 C22 C21 119.8(2) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C24 C23 C22 119.7(2) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C25 C24 C23 120.5(2) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 120.2(2) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C21 119.9(2) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? O31 C32 N33 125.3(3) . . ? O31 C32 H32 117.3 . . ? N33 C32 H32 117.3 . . ? C32 N33 C35 120.5(2) . . ? C32 N33 C34 121.4(2) . . ? C35 N33 C34 118.0(2) . . ? N33 C34 H34A 109.5 . . ? N33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N33 C35 H35A 109.5 . . ? N33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Nd O1 C2 -174.74(18) 2 . . . ? O12 Nd O1 C2 157.49(18) 2 . . . ? O12 Nd O1 C2 -146.98(18) . . . . ? O16 Nd O1 C2 69.83(17) . . . . ? O16 Nd O1 C2 -85.59(18) 2 . . . ? O17 Nd O1 C2 100.14(17) . . . . ? O17 Nd O1 C2 -70.65(17) 2 . . . ? N4 Nd O1 C2 -0.15(16) . . . . ? N7 Nd O1 C2 5.26(18) . . . . ? N11 Nd O1 C2 -174.74(18) . . . . ? Nd O1 C2 N3 2.3(3) . . . . ? Nd O1 C2 C21 -177.92(13) . . . . ? O1 C2 N3 N4 -3.9(3) . . . . ? C21 C2 N3 N4 176.24(18) . . . . ? C2 N3 N4 C5 -175.69(19) . . . . ? C2 N3 N4 Nd 3.7(2) . . . . ? O1 Nd N4 C5 177.44(19) . . . . ? O12 Nd N4 C5 153.65(16) 2 . . . ? O12 Nd N4 C5 -148.71(16) . . . . ? O16 Nd N4 C5 93.95(18) . . . . ? O16 Nd N4 C5 -63.44(18) 2 . . . ? O17 Nd N4 C5 74.49(18) . . . . ? O17 Nd N4 C5 -96.69(18) 2 . . . ? N4 Nd N4 C5 3.13(15) 2 . . . ? N7 Nd N4 C5 3.13(15) . . . . ? N11 Nd N4 C5 -176.87(15) . . . . ? O1 Nd N4 N3 -1.87(13) . . . . ? O12 Nd N4 N3 -25.67(16) 2 . . . ? O12 Nd N4 N3 31.97(15) . . . . ? O16 Nd N4 N3 -85.37(14) . . . . ? O16 Nd N4 N3 117.25(14) 2 . . . ? O17 Nd N4 N3 -104.83(14) . . . . ? O17 Nd N4 N3 83.99(14) 2 . . . ? N4 Nd N4 N3 -176.19(15) 2 . . . ? N7 Nd N4 N3 -176.19(15) . . . . ? N11 Nd N4 N3 3.81(15) . . . . ? N3 N4 C5 C6 176.19(17) . . . . ? Nd N4 C5 C6 -3.1(3) . . . . ? N4 C5 C6 N7 0.1(3) . . . . ? N4 C5 C6 C8 -178.1(2) . . . . ? C8 C6 N7 C6 0.85(15) . . . 2 ? C5 C6 N7 C6 -177.2(2) . . . 2 ? C8 C6 N7 Nd -179.15(15) . . . . ? C5 C6 N7 Nd 2.8(2) . . . . ? O1 Nd N7 C6 171.69(10) . . . 2 ? O1 Nd N7 C6 -8.31(10) 2 . . 2 ? O12 Nd N7 C6 81.77(13) 2 . . 2 ? O12 Nd N7 C6 -98.23(13) . . . 2 ? O16 Nd N7 C6 110.18(10) . . . 2 ? O16 Nd N7 C6 -69.82(10) 2 . . 2 ? O17 Nd N7 C6 61.28(10) . . . 2 ? O17 Nd N7 C6 -118.72(10) 2 . . 2 ? N4 Nd N7 C6 -2.86(10) 2 . . 2 ? N4 Nd N7 C6 177.14(10) . . . 2 ? O1 Nd N7 C6 -8.31(10) . . . . ? O1 Nd N7 C6 171.69(10) 2 . . . ? O12 Nd N7 C6 -98.23(13) 2 . . . ? O12 Nd N7 C6 81.77(13) . . . . ? O16 Nd N7 C6 -69.82(10) . . . . ? O16 Nd N7 C6 110.18(10) 2 . . . ? O17 Nd N7 C6 -118.72(10) . . . . ? O17 Nd N7 C6 61.28(10) 2 . . . ? N4 Nd N7 C6 177.14(10) 2 . . . ? N4 Nd N7 C6 -2.86(10) . . . . ? N7 C6 C8 C9 -1.7(3) . . . . ? C5 C6 C8 C9 176.36(16) . . . . ? C6 C8 C9 C8 0.79(14) . . . 2 ? O1 Nd N11 O12 -89.92(9) . . . 2 ? O1 Nd N11 O12 90.08(9) 2 . . 2 ? O12 Nd N11 O12 180.0 . . . 2 ? O16 Nd N11 O12 -28.41(9) . . . 2 ? O16 Nd N11 O12 151.59(9) 2 . . 2 ? O17 Nd N11 O12 20.50(9) . . . 2 ? O17 Nd N11 O12 -159.50(9) 2 . . 2 ? N4 Nd N11 O12 84.63(9) 2 . . 2 ? N4 Nd N11 O12 -95.37(9) . . . 2 ? O1 Nd N11 O12 90.08(9) . . . . ? O1 Nd N11 O12 -89.92(9) 2 . . . ? O12 Nd N11 O12 180.0 2 . . . ? O16 Nd N11 O12 151.59(9) . . . . ? O16 Nd N11 O12 -28.41(9) 2 . . . ? O17 Nd N11 O12 -159.50(9) . . . . ? O17 Nd N11 O12 20.50(9) 2 . . . ? N4 Nd N11 O12 -95.37(9) 2 . . . ? N4 Nd N11 O12 84.63(9) . . . . ? O13 N11 O12 Nd 180.0 . . . . ? O12 N11 O12 Nd 0.0 2 . . . ? O1 Nd O12 N11 -77.78(8) . . . . ? O1 Nd O12 N11 77.92(8) 2 . . . ? O12 Nd O12 N11 0.0 2 . . . ? O16 Nd O12 N11 -34.21(11) . . . . ? O16 Nd O12 N11 151.94(9) 2 . . . ? O17 Nd O12 N11 23.35(11) . . . . ? O17 Nd O12 N11 -158.41(10) 2 . . . ? N4 Nd O12 N11 100.16(9) 2 . . . ? N4 Nd O12 N11 -109.26(8) . . . . ? N7 Nd O12 N11 180.0 . . . . ? O18 N15 O16 Nd 176.8(2) . . . . ? O17 N15 O16 Nd -3.3(2) . . . . ? O1 Nd O16 N15 143.00(16) . . . . ? O1 Nd O16 N15 21.13(17) 2 . . . ? O12 Nd O16 N15 75.46(15) 2 . . . ? O12 Nd O16 N15 101.48(15) . . . . ? O16 Nd O16 N15 -92.71(14) 2 . . . ? O17 Nd O16 N15 1.89(13) . . . . ? O17 Nd O16 N15 -165.72(13) 2 . . . ? N4 Nd O16 N15 -39.59(15) 2 . . . ? N4 Nd O16 N15 -153.37(16) . . . . ? N7 Nd O16 N15 -92.71(14) . . . . ? N11 Nd O16 N15 87.29(14) . . . . ? O18 N15 O17 Nd -176.9(2) . . . . ? O16 N15 O17 Nd 3.2(2) . . . . ? O1 Nd O17 N15 -41.37(15) . . . . ? O1 Nd O17 N15 -164.82(15) 2 . . . ? O12 Nd O17 N15 -95.49(14) 2 . . . ? O12 Nd O17 N15 -114.26(14) . . . . ? O16 Nd O17 N15 -1.88(13) . . . . ? O16 Nd O17 N15 144.90(14) 2 . . . ? N4 Nd O17 N15 132.71(15) 2 . . . ? N4 Nd O17 N15 21.51(15) . . . . ? N7 Nd O17 N15 75.47(14) . . . . ? N11 Nd O17 N15 -104.53(14) . . . . ? O1 C2 C21 C26 -167.9(2) . . . . ? N3 C2 C21 C26 11.9(3) . . . . ? O1 C2 C21 C22 8.7(3) . . . . ? N3 C2 C21 C22 -171.44(19) . . . . ? C26 C21 C22 C23 -0.6(3) . . . . ? C2 C21 C22 C23 -177.4(2) . . . . ? C21 C22 C23 C24 0.4(4) . . . . ? C22 C23 C24 C25 0.0(5) . . . . ? C23 C24 C25 C26 -0.1(4) . . . . ? C24 C25 C26 C21 -0.1(4) . . . . ? C22 C21 C26 C25 0.5(3) . . . . ? C2 C21 C26 C25 177.0(2) . . . . ? O31 C32 N33 C35 3.6(5) . . . . ? O31 C32 N33 C34 -173.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.248 _refine_diff_density_min -0.920 _refine_diff_density_rms 0.074 # Attachment 'fro4511.cif' data_fro4511 _database_code_depnum_ccdc_archive 'CCDC 728921' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H30 Br4 F9 N10 O13 Pr S3' _chemical_formula_weight 1646.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.9360(1) _cell_length_b 13.9724(1) _cell_length_c 19.8120(3) _cell_angle_alpha 92.500(1) _cell_angle_beta 105.367(1) _cell_angle_gamma 112.917(1) _cell_volume 3136.64(6) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3147 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.88 _exptl_crystal_description column _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.743 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1604 _exptl_absorpt_coefficient_mu 3.514 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3008 _exptl_absorpt_correction_T_max 0.6207 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33961 _diffrn_reflns_av_R_equivalents 0.047 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 28.28 _reflns_number_total 15220 _reflns_number_gt 11889 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Anions in part disordered, one (C - D) refined with split positions using PART, in addition geometrical (DFIX) and thermal (ISOR) restraints are applied. ; _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^)+(0.1342P)^2^+10.9100P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 15220 _refine_ls_number_parameters 839 _refine_ls_number_restraints 483 _refine_ls_R_factor_all 0.0917 _refine_ls_R_factor_gt 0.0710 _refine_ls_wR_factor_ref 0.2203 _refine_ls_wR_factor_gt 0.2029 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.017 0.493 0.026 10 7 ' ' 2 0.024 0.510 0.962 6 3 ' ' 3 0.116 0.425 0.927 14 2 ' ' 4 0.382 0.156 0.846 166 42 ' ' 5 0.619 0.842 0.155 164 42 ' ' 6 0.884 0.575 0.073 15 3 ' ' _platon_squeeze_details ; The results of the squeeze routine were appended to the CIF to give the locations of the voids and the content of them. The SQUEEZE routine was not used, the corrected HKL-file did not improve the model. ; 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 Pr Pr -0.79453(3) 0.24720(2) 0.290078(16) 0.02680(11) Uani 1 1 d . . . O1A O -0.6502(4) 0.2490(3) 0.4081(2) 0.0345(9) Uani 1 1 d U . . C2A C -0.5594(5) 0.3242(5) 0.4442(3) 0.0304(12) Uani 1 1 d U . . C21A C -0.4874(5) 0.3153(5) 0.5136(3) 0.0325(12) Uani 1 1 d U . . C22A C -0.5364(6) 0.2302(5) 0.5465(4) 0.0426(16) Uani 1 1 d U . . H22A H -0.6159 0.1833 0.5263 0.051 Uiso 1 1 calc R . . C23A C -0.4711(7) 0.2138(6) 0.6075(4) 0.0486(18) Uani 1 1 d U . . H23A H -0.5050 0.1565 0.6296 0.058 Uiso 1 1 calc R . . C24A C -0.3525(6) 0.2842(5) 0.6365(4) 0.0405(15) Uani 1 1 d U . . C25A C -0.3025(6) 0.3709(6) 0.6073(4) 0.0447(16) Uani 1 1 d U . . H25A H -0.2238 0.4193 0.6287 0.054 Uiso 1 1 calc R . . C26A C -0.3705(6) 0.3857(5) 0.5453(4) 0.0427(16) Uani 1 1 d U . . H26A H -0.3370 0.4444 0.5242 0.051 Uiso 1 1 calc R . . Br1A Br -0.25998(7) 0.25765(6) 0.71912(4) 0.0580(2) Uani 1 1 d . . . N3A N -0.5215(4) 0.4163(4) 0.4201(3) 0.0337(11) Uani 1 1 d . . . H3A H -0.4582 0.4706 0.4448 0.040 Uiso 1 1 calc R . . N4A N -0.5884(4) 0.4198(4) 0.3543(3) 0.0303(10) Uani 1 1 d . . . C5A C -0.5506(6) 0.5059(5) 0.3294(4) 0.0372(14) Uani 1 1 d U . . H5A H -0.4810 0.5637 0.3558 0.045 Uiso 1 1 calc R . . C6A C -0.6181(6) 0.5118(5) 0.2594(3) 0.0365(13) Uani 1 1 d U . . N7A N -0.7167(5) 0.4248(4) 0.2255(3) 0.0345(11) Uani 1 1 d . . . C8A C -0.5765(9) 0.6029(6) 0.2301(5) 0.061(2) Uani 1 1 d U . . H8A H -0.5058 0.6607 0.2551 0.074 Uiso 1 1 calc R . . C9A C -0.6421(11) 0.6059(7) 0.1635(5) 0.078(3) Uani 1 1 d U . . H9A H -0.6187 0.6672 0.1430 0.094 Uiso 1 1 calc R . . C8B C -0.7439(11) 0.5164(8) 0.1268(5) 0.076(3) Uani 1 1 d U . . H8B H -0.7893 0.5167 0.0811 0.091 Uiso 1 1 calc R . . C6B C -0.7775(7) 0.4265(6) 0.1588(4) 0.0458(16) Uani 1 1 d U . . C5B C -0.8729(8) 0.3306(6) 0.1199(4) 0.0526(19) Uani 1 1 d U . . H5B H -0.9193 0.3284 0.0740 0.063 Uiso 1 1 calc R . . N4B N -0.8945(5) 0.2477(5) 0.1486(3) 0.0435(13) Uani 1 1 d . . . N3B N -0.9785(6) 0.1536(5) 0.1091(3) 0.0516(16) Uani 1 1 d . . . H3B H -1.0197 0.1486 0.0655 0.062 Uiso 1 1 calc R . . C2B C -0.9934(6) 0.0694(6) 0.1422(4) 0.0397(14) Uani 1 1 d U . . C21B C -1.0792(7) -0.0384(6) 0.1031(4) 0.0503(18) Uani 1 1 d U . . C22B C -1.0967(7) -0.1197(6) 0.1403(4) 0.0532(19) Uani 1 1 d U . . H22B H -1.0550 -0.1062 0.1890 0.064 Uiso 1 1 calc R . . C23B C -1.1748(8) -0.2226(8) 0.1083(5) 0.064(2) Uani 1 1 d U . . H23B H -1.1875 -0.2778 0.1350 0.077 Uiso 1 1 calc R . . C24B C -1.2327(9) -0.2416(8) 0.0371(6) 0.072(3) Uani 1 1 d U . . C25B C -1.2114(10) -0.1612(9) -0.0037(6) 0.078(3) Uani 1 1 d U . . H25B H -1.2454 -0.1753 -0.0532 0.093 Uiso 1 1 calc R . . C26B C -1.1378(9) -0.0596(8) 0.0319(5) 0.068(2) Uani 1 1 d U . . H26B H -1.1278 -0.0033 0.0063 0.081 Uiso 1 1 calc R . . Br1B Br -1.33920(14) -0.38127(10) -0.00619(8) 0.1161(6) Uani 1 1 d . . . O1B O -0.9374(4) 0.0813(4) 0.2055(2) 0.0427(11) Uani 1 1 d U . . O1C O -0.6506(4) 0.2587(4) 0.2221(3) 0.0431(11) Uani 1 1 d U . . C2C C -0.5903(6) 0.2072(6) 0.2263(4) 0.0402(15) Uani 1 1 d U . . C21C C -0.4964(7) 0.2343(7) 0.1909(4) 0.0501(18) Uani 1 1 d U . . C22C C -0.4693(8) 0.3259(8) 0.1621(5) 0.064(2) Uani 1 1 d U . . H22C H -0.5077 0.3698 0.1662 0.077 Uiso 1 1 calc R . . C23C C -0.3849(10) 0.3525(10) 0.1269(6) 0.082(3) Uani 1 1 d U . . H23C H -0.3687 0.4130 0.1052 0.098 Uiso 1 1 calc R . . C24C C -0.3254(10) 0.2914(12) 0.1236(6) 0.086(3) Uani 1 1 d U . . C25C C -0.3508(10) 0.2004(11) 0.1522(7) 0.088(3) Uani 1 1 d U . . H25C H -0.3105 0.1580 0.1483 0.106 Uiso 1 1 calc R . . C26C C -0.4369(8) 0.1705(9) 0.1871(5) 0.068(3) Uani 1 1 d U . . H26C H -0.4542 0.1089 0.2075 0.082 Uiso 1 1 calc R . . Br1C Br -0.21193(15) 0.3281(2) 0.07473(9) 0.1760(11) Uani 1 1 d . . . N3C N -0.6074(5) 0.1279(5) 0.2641(4) 0.0441(14) Uani 1 1 d . . . H3C H -0.5640 0.0927 0.2699 0.053 Uiso 1 1 calc R . . N4C N -0.6976(5) 0.1064(4) 0.2929(3) 0.0366(12) Uani 1 1 d . . . C5C C -0.7196(6) 0.0276(6) 0.3268(5) 0.0473(17) Uani 1 1 d U . . H5C H -0.6747 -0.0123 0.3323 0.057 Uiso 1 1 calc R . . C6C C -0.8181(6) 0.0030(5) 0.3565(4) 0.0422(15) Uani 1 1 d U . . N7C N -0.8743(4) 0.0663(4) 0.3471(3) 0.0308(10) Uani 1 1 d . . . C8C C -0.8512(8) -0.0841(7) 0.3907(5) 0.061(2) Uani 1 1 d U . . H8C H -0.8078 -0.1253 0.3975 0.073 Uiso 1 1 calc R . . C9C C -0.9473(8) -0.1093(7) 0.4144(6) 0.064(2) Uani 1 1 d U . . H9C H -0.9707 -0.1673 0.4380 0.076 Uiso 1 1 calc R . . C8D C -1.0087(7) -0.0476(6) 0.4026(5) 0.0497(18) Uani 1 1 d U . . H8D H -1.0762 -0.0636 0.4173 0.060 Uiso 1 1 calc R . . C6D C -0.9701(5) 0.0394(5) 0.3687(3) 0.0334(12) Uani 1 1 d U . . C5D C -1.0355(6) 0.1043(5) 0.3529(4) 0.0381(14) Uani 1 1 d U . . H5D H -1.1014 0.0920 0.3686 0.046 Uiso 1 1 calc R . . N4D N -1.0013(4) 0.1785(4) 0.3174(3) 0.0321(11) Uani 1 1 d . . . N3D N -1.0642(4) 0.2392(4) 0.3047(3) 0.0371(12) Uani 1 1 d . . . H3D H -1.1340 0.2191 0.3097 0.045 Uiso 1 1 calc R . . C2D C -1.0111(5) 0.3319(5) 0.2839(3) 0.0342(13) Uani 1 1 d U . . C21D C -1.0697(6) 0.4061(5) 0.2802(4) 0.0375(14) Uani 1 1 d U . . C22D C -1.1614(6) 0.3920(6) 0.3077(4) 0.0444(16) Uani 1 1 d U . . H22D H -1.1911 0.3324 0.3288 0.053 Uiso 1 1 calc R . . C23D C -1.2095(7) 0.4645(6) 0.3044(5) 0.0515(18) Uani 1 1 d U . . H23D H -1.2713 0.4553 0.3235 0.062 Uiso 1 1 calc R . . C24D C -1.1658(8) 0.5504(7) 0.2727(5) 0.0543(19) Uani 1 1 d U . . C25D C -1.0747(8) 0.5666(7) 0.2455(5) 0.0555(19) Uani 1 1 d U . . H25D H -1.0460 0.6262 0.2241 0.067 Uiso 1 1 calc R . . C26D C -1.0261(7) 0.4953(6) 0.2496(4) 0.0452(16) Uani 1 1 d U . . H26D H -0.9627 0.5065 0.2317 0.054 Uiso 1 1 calc R . . Br1D Br -1.23131(12) 0.65202(10) 0.27022(8) 0.0903(4) Uani 1 1 d . . . O1D O -0.9184(4) 0.3534(4) 0.2693(2) 0.0364(10) Uani 1 1 d U . . S1A S -0.80456(14) 0.33086(13) 0.48391(9) 0.0376(4) Uani 1 1 d . . . O11A O -0.8044(4) 0.3451(4) 0.4117(3) 0.0417(11) Uani 1 1 d U . . O12A O -0.6962(4) 0.4004(4) 0.5374(3) 0.0482(12) Uani 1 1 d U . . O13A O -0.8539(5) 0.2249(4) 0.4956(3) 0.0516(13) Uani 1 1 d U . . C11A C -0.9114(7) 0.3814(7) 0.4960(5) 0.0520(18) Uani 1 1 d U . . F11A F -0.9230(5) 0.3759(5) 0.5600(3) 0.0743(15) Uani 1 1 d U . . F12A F -1.0180(5) 0.3238(6) 0.4512(3) 0.0894(19) Uani 1 1 d U . . F13A F -0.8797(6) 0.4800(5) 0.4867(4) 0.097(2) Uani 1 1 d U . . S1B S 0.65442(18) 0.07418(17) 0.37045(15) 0.0609(6) Uani 1 1 d D . . O11B O 0.5341(5) 0.0213(5) 0.3294(4) 0.0635(16) Uani 1 1 d DU . . O12B O 0.7268(5) 0.1506(5) 0.3376(4) 0.0680(17) Uani 1 1 d DU . . O13B O 0.7084(6) 0.0118(6) 0.4079(5) 0.097(3) Uani 1 1 d DU . . C11B C 0.6476(11) 0.1564(11) 0.4404(7) 0.112(5) Uani 1 1 d DU . . F11B F 0.6026(8) 0.2232(7) 0.4095(5) 0.131(3) Uani 1 1 d DU . . F12B F 0.5844(10) 0.1009(10) 0.4795(6) 0.163(4) Uani 1 1 d DU . . F13B F 0.7541(8) 0.2153(8) 0.4874(5) 0.130(3) Uani 1 1 d DU . . S1C S -1.1625(4) 0.1179(3) -0.1024(2) 0.0535(13) Uani 0.495(6) 1 d PD A 1 O11C O -1.1324(13) 0.1769(12) -0.1564(7) 0.068(4) Uani 0.495(6) 1 d PDU A 1 O12C O -1.0885(14) 0.1659(11) -0.0304(6) 0.061(4) Uani 0.495(6) 1 d PDU A 1 O13C O -1.1940(15) 0.0074(9) -0.1187(8) 0.067(4) Uani 0.495(6) 1 d PDU A 1 C11C C -1.3007(13) 0.1230(12) -0.1019(9) 0.063(5) Uani 0.495(6) 1 d PDU A 1 F11C F -1.3828(16) 0.0774(14) -0.1641(8) 0.100(6) Uani 0.495(6) 1 d PDU A 1 F12C F -1.341(2) 0.0757(18) -0.0517(11) 0.130(8) Uani 0.495(6) 1 d PDU A 1 F13C F -1.2870(12) 0.2218(9) -0.0913(7) 0.086(4) Uani 0.495(6) 1 d PDU A 1 S1D S -1.1150(3) 0.2246(3) -0.08925(18) 0.0447(11) Uani 0.505(6) 1 d PD A 2 O11D O -1.0833(12) 0.2368(12) -0.1529(6) 0.059(3) Uani 0.505(6) 1 d PDU A 2 O12D O -1.0386(12) 0.1966(12) -0.0342(7) 0.058(4) Uani 0.505(6) 1 d PDU A 2 O13D O -1.1494(14) 0.3016(11) -0.0651(8) 0.079(4) Uani 0.505(6) 1 d PDU A 2 C11D C -1.2501(14) 0.1050(12) -0.1134(9) 0.066(5) Uani 0.505(6) 1 d PDU A 2 F11D F -1.3369(16) 0.1108(17) -0.1680(9) 0.109(6) Uani 0.505(6) 1 d PDU A 2 F12D F -1.2937(16) 0.0785(15) -0.0597(8) 0.102(5) Uani 0.505(6) 1 d PDU A 2 F13D F -1.2303(18) 0.0250(16) -0.1350(11) 0.122(7) Uani 0.505(6) 1 d PDU A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pr 0.02518(17) 0.02538(17) 0.02578(17) 0.00584(12) 0.00428(11) 0.00849(12) O1A 0.028(2) 0.028(2) 0.033(2) 0.0050(17) 0.0010(16) 0.0027(16) C2A 0.028(3) 0.028(3) 0.032(3) 0.006(2) 0.007(2) 0.009(2) C21A 0.030(3) 0.029(3) 0.029(3) 0.009(2) 0.002(2) 0.007(2) C22A 0.036(3) 0.032(3) 0.041(3) 0.014(3) 0.001(3) 0.001(3) C23A 0.046(4) 0.036(3) 0.047(4) 0.021(3) 0.005(3) 0.005(3) C24A 0.045(3) 0.036(3) 0.035(3) 0.012(3) 0.004(3) 0.016(3) C25A 0.035(3) 0.036(3) 0.045(4) 0.013(3) -0.001(3) 0.005(3) C26A 0.038(3) 0.034(3) 0.040(3) 0.018(3) 0.001(3) 0.004(3) Br1A 0.0579(5) 0.0474(4) 0.0513(5) 0.0200(4) -0.0082(4) 0.0192(4) N3A 0.028(2) 0.026(2) 0.030(3) 0.009(2) 0.0000(19) -0.0005(19) N4A 0.033(2) 0.026(2) 0.024(2) 0.0067(19) 0.0044(19) 0.008(2) C5A 0.042(3) 0.029(3) 0.035(3) 0.011(2) 0.010(3) 0.009(2) C6A 0.049(3) 0.028(3) 0.031(3) 0.011(2) 0.012(3) 0.014(3) N7A 0.046(3) 0.034(3) 0.028(3) 0.011(2) 0.010(2) 0.021(2) C8A 0.087(5) 0.031(3) 0.050(4) 0.015(3) 0.012(4) 0.012(4) C9A 0.120(7) 0.042(4) 0.054(5) 0.019(4) 0.003(5) 0.028(5) C8B 0.113(7) 0.052(5) 0.049(4) 0.021(4) -0.005(4) 0.038(5) C6B 0.064(4) 0.042(4) 0.034(3) 0.011(3) 0.006(3) 0.030(3) C5B 0.066(4) 0.052(4) 0.035(4) 0.008(3) -0.005(3) 0.033(4) N4B 0.050(3) 0.042(3) 0.030(3) 0.003(2) -0.003(2) 0.020(3) N3B 0.056(4) 0.048(4) 0.031(3) 0.001(3) -0.011(3) 0.018(3) C2B 0.041(3) 0.040(3) 0.033(3) 0.000(3) 0.003(3) 0.019(3) C21B 0.049(4) 0.045(4) 0.043(4) -0.004(3) -0.004(3) 0.020(3) C22B 0.052(4) 0.048(4) 0.042(4) -0.002(3) -0.002(3) 0.015(3) C23B 0.061(5) 0.058(5) 0.059(5) -0.001(4) 0.005(4) 0.022(4) C24B 0.070(5) 0.052(5) 0.068(5) -0.010(4) -0.007(4) 0.018(4) C25B 0.078(6) 0.072(6) 0.053(5) -0.005(4) -0.010(4) 0.022(5) C26B 0.072(5) 0.056(5) 0.051(4) 0.000(4) -0.007(4) 0.020(4) Br1B 0.1189(11) 0.0564(7) 0.0982(10) -0.0244(6) -0.0335(8) 0.0072(7) O1B 0.050(3) 0.040(3) 0.029(2) 0.0007(19) 0.0016(19) 0.017(2) O1C 0.049(3) 0.048(3) 0.043(3) 0.016(2) 0.022(2) 0.025(2) C2C 0.037(3) 0.041(3) 0.040(3) 0.002(3) 0.012(3) 0.014(3) C21C 0.044(4) 0.059(4) 0.043(4) -0.002(3) 0.018(3) 0.016(3) C22C 0.064(5) 0.077(6) 0.050(4) 0.014(4) 0.030(4) 0.020(4) C23C 0.076(6) 0.100(7) 0.060(5) 0.014(5) 0.036(5) 0.018(5) C24C 0.070(5) 0.121(8) 0.065(6) -0.007(5) 0.036(5) 0.030(5) C25C 0.072(6) 0.119(8) 0.086(6) -0.016(5) 0.033(5) 0.049(5) C26C 0.055(4) 0.087(6) 0.067(5) -0.008(4) 0.025(4) 0.032(4) Br1C 0.0991(11) 0.342(3) 0.0832(10) 0.0063(14) 0.0669(9) 0.0659(15) N3C 0.033(3) 0.038(3) 0.064(4) 0.003(3) 0.018(3) 0.017(2) N4C 0.031(3) 0.030(3) 0.046(3) 0.005(2) 0.011(2) 0.011(2) C5C 0.038(3) 0.035(3) 0.074(5) 0.019(3) 0.017(3) 0.020(3) C6C 0.030(3) 0.035(3) 0.059(4) 0.018(3) 0.009(3) 0.012(3) N7C 0.027(2) 0.023(2) 0.034(3) 0.006(2) 0.0031(19) 0.0052(19) C8C 0.057(4) 0.048(4) 0.089(6) 0.036(4) 0.025(4) 0.029(4) C9C 0.063(5) 0.047(4) 0.088(6) 0.039(4) 0.031(4) 0.023(4) C8D 0.046(4) 0.038(4) 0.065(5) 0.022(3) 0.025(3) 0.010(3) C6D 0.030(3) 0.028(3) 0.036(3) 0.007(2) 0.010(2) 0.006(2) C5D 0.032(3) 0.033(3) 0.048(4) 0.008(3) 0.018(3) 0.008(2) N4D 0.026(2) 0.025(2) 0.040(3) 0.004(2) 0.007(2) 0.0072(19) N3D 0.025(2) 0.031(3) 0.054(3) 0.008(2) 0.012(2) 0.011(2) C2D 0.031(3) 0.030(3) 0.036(3) 0.004(2) 0.005(2) 0.011(2) C21D 0.033(3) 0.032(3) 0.045(4) 0.007(3) 0.008(3) 0.014(2) C22D 0.040(3) 0.036(3) 0.058(4) 0.009(3) 0.017(3) 0.015(3) C23D 0.046(4) 0.053(4) 0.066(5) 0.014(4) 0.021(3) 0.029(3) C24D 0.057(4) 0.052(4) 0.065(5) 0.018(4) 0.017(4) 0.034(4) C25D 0.060(4) 0.051(4) 0.064(5) 0.021(4) 0.020(4) 0.030(4) C26D 0.046(4) 0.039(3) 0.055(4) 0.015(3) 0.019(3) 0.019(3) Br1D 0.1145(9) 0.0873(8) 0.1287(10) 0.0565(8) 0.0650(8) 0.0807(8) O1D 0.032(2) 0.038(2) 0.044(2) 0.015(2) 0.0146(19) 0.0164(18) S1A 0.0300(7) 0.0304(8) 0.0396(9) 0.0080(6) 0.0076(6) 0.0010(6) O11A 0.033(2) 0.043(3) 0.039(2) 0.008(2) 0.0103(19) 0.0068(19) O12A 0.037(2) 0.037(3) 0.047(3) 0.009(2) 0.002(2) -0.001(2) O13A 0.056(3) 0.030(2) 0.053(3) 0.012(2) 0.018(2) 0.001(2) C11A 0.050(4) 0.048(4) 0.056(4) 0.008(3) 0.022(3) 0.014(3) F11A 0.084(4) 0.077(4) 0.064(3) 0.004(3) 0.036(3) 0.028(3) F12A 0.044(3) 0.132(5) 0.080(4) -0.013(3) 0.013(3) 0.032(3) F13A 0.101(4) 0.076(4) 0.150(6) 0.050(4) 0.071(4) 0.049(3) S1B 0.0417(10) 0.0535(12) 0.1018(18) 0.0350(12) 0.0366(11) 0.0226(9) O11B 0.041(3) 0.059(3) 0.096(4) 0.035(3) 0.025(3) 0.022(3) O12B 0.056(3) 0.049(3) 0.109(5) 0.026(3) 0.049(3) 0.016(3) O13B 0.063(4) 0.080(5) 0.157(7) 0.056(5) 0.027(4) 0.039(4) C11B 0.092(7) 0.125(9) 0.129(9) 0.021(7) 0.031(6) 0.056(7) F11B 0.143(6) 0.146(6) 0.134(6) -0.008(5) 0.014(5) 0.111(5) F12B 0.159(7) 0.212(8) 0.148(7) 0.042(6) 0.107(6) 0.067(6) F13B 0.126(6) 0.134(6) 0.118(6) -0.006(5) 0.010(5) 0.062(5) S1C 0.063(3) 0.052(2) 0.0345(19) 0.0069(16) -0.0054(17) 0.026(2) O11C 0.069(7) 0.076(8) 0.054(6) 0.023(6) 0.008(5) 0.031(6) O12C 0.065(7) 0.059(7) 0.042(6) 0.013(5) -0.008(5) 0.024(6) O13C 0.076(8) 0.053(7) 0.063(7) -0.010(5) 0.002(6) 0.032(6) C11C 0.068(8) 0.065(8) 0.059(8) 0.010(7) 0.017(7) 0.033(7) F11C 0.090(9) 0.096(9) 0.098(9) 0.019(7) -0.001(7) 0.041(7) F12C 0.131(12) 0.137(11) 0.126(11) 0.037(8) 0.048(8) 0.054(8) F13C 0.094(7) 0.077(7) 0.094(7) 0.014(5) 0.013(5) 0.054(6) S1D 0.056(2) 0.049(2) 0.0329(18) 0.0137(15) 0.0152(15) 0.0239(17) O11D 0.057(6) 0.079(7) 0.044(6) 0.023(5) 0.015(5) 0.032(5) O12D 0.059(7) 0.066(7) 0.040(6) 0.020(5) 0.003(5) 0.021(6) O13D 0.099(8) 0.067(7) 0.087(8) 0.022(6) 0.045(6) 0.039(6) C11D 0.063(8) 0.076(9) 0.061(8) 0.021(7) 0.017(7) 0.030(7) F11D 0.086(9) 0.123(10) 0.100(9) 0.050(7) 0.010(6) 0.035(7) F12D 0.102(9) 0.099(8) 0.099(8) 0.050(7) 0.029(7) 0.034(6) F13D 0.125(11) 0.109(10) 0.118(11) -0.006(8) 0.018(8) 0.048(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pr O1B 2.506(5) . ? Pr O1C 2.533(5) . ? Pr O1D 2.549(4) . ? Pr O1A 2.569(4) . ? Pr N4D 2.680(5) . ? Pr N4C 2.709(5) . ? Pr N4A 2.733(5) . ? Pr N7C 2.750(5) . ? Pr N4B 2.760(6) . ? Pr O11A 2.775(5) . ? Pr N7A 2.797(5) . ? O1A C2A 1.235(7) . ? C2A N3A 1.345(8) . ? C2A C21A 1.484(8) . ? C21A C26A 1.390(9) . ? C21A C22A 1.392(9) . ? C22A C23A 1.365(9) . ? C22A H22A 0.9400 . ? C23A C24A 1.400(10) . ? C23A H23A 0.9400 . ? C24A C25A 1.368(10) . ? C24A Br1A 1.900(6) . ? C25A C26A 1.384(9) . ? C25A H25A 0.9400 . ? C26A H26A 0.9400 . ? N3A N4A 1.375(7) . ? N3A H3A 0.8700 . ? N4A C5A 1.285(8) . ? C5A C6A 1.456(9) . ? C5A H5A 0.9400 . ? C6A N7A 1.350(9) . ? C6A C8A 1.393(10) . ? N7A C6B 1.354(8) . ? C8A C9A 1.379(13) . ? C8A H8A 0.9400 . ? C9A C8B 1.399(15) . ? C9A H9A 0.9400 . ? C8B C6B 1.399(11) . ? C8B H8B 0.9400 . ? C6B C5B 1.425(11) . ? C5B N4B 1.277(10) . ? C5B H5B 0.9400 . ? N4B N3B 1.367(8) . ? N3B C2B 1.345(9) . ? N3B H3B 0.8700 . ? C2B O1B 1.239(8) . ? C2B C21B 1.497(10) . ? C21B C22B 1.359(12) . ? C21B C26B 1.368(11) . ? C22B C23B 1.393(12) . ? C22B H22B 0.9400 . ? C23B C24B 1.368(13) . ? C23B H23B 0.9400 . ? C24B C25B 1.396(15) . ? C24B Br1B 1.891(9) . ? C25B C26B 1.387(13) . ? C25B H25B 0.9400 . ? C26B H26B 0.9400 . ? O1C C2C 1.242(8) . ? C2C N3C 1.344(10) . ? C2C C21C 1.491(10) . ? C21C C22C 1.382(13) . ? C21C C26C 1.396(12) . ? C22C C23C 1.388(13) . ? C22C H22C 0.9400 . ? C23C C24C 1.364(18) . ? C23C H23C 0.9400 . ? C24C C25C 1.372(18) . ? C24C Br1C 1.888(10) . ? C25C C26C 1.403(14) . ? C25C H25C 0.9400 . ? C26C H26C 0.9400 . ? N3C N4C 1.368(8) . ? N3C H3C 0.8700 . ? N4C C5C 1.292(9) . ? C5C C6C 1.470(10) . ? C5C H5C 0.9400 . ? C6C N7C 1.338(8) . ? C6C C8C 1.394(10) . ? N7C C6D 1.339(8) . ? C8C C9C 1.368(13) . ? C8C H8C 0.9400 . ? C9C C8D 1.372(12) . ? C9C H9C 0.9400 . ? C8D C6D 1.399(9) . ? C8D H8D 0.9400 . ? C6D C5D 1.454(9) . ? C5D N4D 1.280(8) . ? C5D H5D 0.9400 . ? N4D N3D 1.376(7) . ? N3D C2D 1.350(8) . ? N3D H3D 0.8700 . ? C2D O1D 1.233(8) . ? C2D C21D 1.499(9) . ? C21D C22D 1.383(10) . ? C21D C26D 1.392(10) . ? C22D C23D 1.376(10) . ? C22D H22D 0.9400 . ? C23D C24D 1.370(12) . ? C23D H23D 0.9400 . ? C24D C25D 1.367(12) . ? C24D Br1D 1.913(8) . ? C25D C26D 1.365(10) . ? C25D H25D 0.9400 . ? C26D H26D 0.9400 . ? S1A O13A 1.423(5) . ? S1A O12A 1.447(5) . ? S1A O11A 1.454(5) . ? S1A C11A 1.840(8) . ? C11A F13A 1.312(10) . ? C11A F11A 1.318(10) . ? C11A F12A 1.327(10) . ? S1B O11B 1.417(6) . ? S1B O12B 1.430(6) . ? S1B O13B 1.433(7) . ? S1B C11B 1.804(13) . ? C11B F12B 1.327(13) . ? C11B F13B 1.346(13) . ? C11B F11B 1.368(13) . ? S1C O11C 1.422(12) . ? S1C O13C 1.433(12) . ? S1C O12C 1.447(11) . ? S1C C11C 1.820(14) . ? C11C F13C 1.320(15) . ? C11C F11C 1.327(16) . ? C11C F12C 1.330(16) . ? S1D O11D 1.423(10) . ? S1D O13D 1.423(11) . ? S1D O12D 1.443(11) . ? S1D C11D 1.813(14) . ? C11D F13D 1.319(16) . ? C11D F12D 1.332(16) . ? C11D F11D 1.369(16) . ? 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 O1B Pr O1C 87.46(17) . . ? O1B Pr O1D 99.15(16) . . ? O1C Pr O1D 122.26(15) . . ? O1B Pr O1A 123.03(15) . . ? O1C Pr O1A 92.69(15) . . ? O1D Pr O1A 126.93(15) . . ? O1B Pr N4D 70.70(16) . . ? O1C Pr N4D 157.67(17) . . ? O1D Pr N4D 59.45(15) . . ? O1A Pr N4D 102.94(15) . . ? O1B Pr N4C 70.08(16) . . ? O1C Pr N4C 58.40(16) . . ? O1D Pr N4C 169.22(16) . . ? O1A Pr N4C 62.29(16) . . ? N4D Pr N4C 115.34(16) . . ? O1B Pr N4A 159.02(17) . . ? O1C Pr N4A 71.64(16) . . ? O1D Pr N4A 93.81(15) . . ? O1A Pr N4A 58.15(14) . . ? N4D Pr N4A 130.28(16) . . ? N4C Pr N4A 96.38(16) . . ? O1B Pr N7C 62.80(15) . . ? O1C Pr N7C 115.79(16) . . ? O1D Pr N7C 118.03(14) . . ? O1A Pr N7C 66.33(14) . . ? N4D Pr N7C 58.65(15) . . ? N4C Pr N7C 58.19(16) . . ? N4A Pr N7C 124.38(14) . . ? O1B Pr N4B 57.90(17) . . ? O1C Pr N4B 70.07(18) . . ? O1D Pr N4B 66.21(17) . . ? O1A Pr N4B 162.75(18) . . ? N4D Pr N4B 93.55(18) . . ? N4C Pr N4B 106.12(18) . . ? N4A Pr N4B 114.09(17) . . ? N7C Pr N4B 120.11(17) . . ? O1B Pr O11A 131.78(15) . . ? O1C Pr O11A 140.38(15) . . ? O1D Pr O11A 64.46(15) . . ? O1A Pr O11A 63.51(15) . . ? N4D Pr O11A 61.89(15) . . ? N4C Pr O11A 122.85(16) . . ? N4A Pr O11A 68.89(14) . . ? N7C Pr O11A 84.63(15) . . ? N4B Pr O11A 130.65(16) . . ? O1B Pr N7A 114.47(16) . . ? O1C Pr N7A 62.43(16) . . ? O1D Pr N7A 62.84(15) . . ? O1A Pr N7A 115.62(15) . . ? N4D Pr N7A 122.00(16) . . ? N4C Pr N7A 120.40(16) . . ? N4A Pr N7A 57.74(15) . . ? N7C Pr N7A 177.09(15) . . ? N4B Pr N7A 57.37(17) . . ? O11A Pr N7A 98.16(15) . . ? C2A O1A Pr 127.4(4) . . ? O1A C2A N3A 120.2(5) . . ? O1A C2A C21A 121.5(5) . . ? N3A C2A C21A 118.2(5) . . ? C26A C21A C22A 118.6(6) . . ? C26A C21A C2A 122.4(6) . . ? C22A C21A C2A 118.9(5) . . ? C23A C22A C21A 121.3(6) . . ? C23A C22A H22A 119.4 . . ? C21A C22A H22A 119.4 . . ? C22A C23A C24A 118.4(6) . . ? C22A C23A H23A 120.8 . . ? C24A C23A H23A 120.8 . . ? C25A C24A C23A 121.9(6) . . ? C25A C24A Br1A 119.7(5) . . ? C23A C24A Br1A 118.3(5) . . ? C24A C25A C26A 118.4(6) . . ? C24A C25A H25A 120.8 . . ? C26A C25A H25A 120.8 . . ? C25A C26A C21A 121.2(6) . . ? C25A C26A H26A 119.4 . . ? C21A C26A H26A 119.4 . . ? C2A N3A N4A 116.3(5) . . ? C2A N3A H3A 121.9 . . ? N4A N3A H3A 121.9 . . ? C5A N4A N3A 116.9(5) . . ? C5A N4A Pr 125.5(4) . . ? N3A N4A Pr 117.6(3) . . ? N4A C5A C6A 118.4(6) . . ? N4A C5A H5A 120.8 . . ? C6A C5A H5A 120.8 . . ? N7A C6A C8A 124.0(7) . . ? N7A C6A C5A 116.5(5) . . ? C8A C6A C5A 119.5(7) . . ? C6A N7A C6B 117.5(6) . . ? C6A N7A Pr 121.7(4) . . ? C6B N7A Pr 120.8(5) . . ? C9A C8A C6A 118.1(8) . . ? C9A C8A H8A 121.0 . . ? C6A C8A H8A 121.0 . . ? C8A C9A C8B 119.1(8) . . ? C8A C9A H9A 120.4 . . ? C8B C9A H9A 120.4 . . ? C6B C8B C9A 119.3(8) . . ? C6B C8B H8B 120.4 . . ? C9A C8B H8B 120.4 . . ? N7A C6B C8B 121.9(8) . . ? N7A C6B C5B 117.4(6) . . ? C8B C6B C5B 120.6(7) . . ? N4B C5B C6B 118.9(6) . . ? N4B C5B H5B 120.5 . . ? C6B C5B H5B 120.5 . . ? C5B N4B N3B 119.0(6) . . ? C5B N4B Pr 124.1(5) . . ? N3B N4B Pr 116.7(4) . . ? C2B N3B N4B 115.6(6) . . ? C2B N3B H3B 122.2 . . ? N4B N3B H3B 122.2 . . ? O1B C2B N3B 119.8(6) . . ? O1B C2B C21B 119.9(7) . . ? N3B C2B C21B 120.3(6) . . ? C22B C21B C26B 118.7(8) . . ? C22B C21B C2B 117.8(7) . . ? C26B C21B C2B 123.5(8) . . ? C21B C22B C23B 121.7(8) . . ? C21B C22B H22B 119.2 . . ? C23B C22B H22B 119.2 . . ? C24B C23B C22B 118.5(9) . . ? C24B C23B H23B 120.7 . . ? C22B C23B H23B 120.7 . . ? C23B C24B C25B 121.4(9) . . ? C23B C24B Br1B 118.5(8) . . ? C25B C24B Br1B 120.1(7) . . ? C26B C25B C24B 117.3(9) . . ? C26B C25B H25B 121.4 . . ? C24B C25B H25B 121.4 . . ? C21B C26B C25B 122.3(9) . . ? C21B C26B H26B 118.9 . . ? C25B C26B H26B 118.9 . . ? C2B O1B Pr 129.6(5) . . ? C2C O1C Pr 127.0(4) . . ? O1C C2C N3C 120.1(6) . . ? O1C C2C C21C 120.5(7) . . ? N3C C2C C21C 119.4(6) . . ? C22C C21C C26C 120.6(8) . . ? C22C C21C C2C 117.5(7) . . ? C26C C21C C2C 121.9(8) . . ? C21C C22C C23C 119.4(10) . . ? C21C C22C H22C 120.3 . . ? C23C C22C H22C 120.3 . . ? C24C C23C C22C 120.3(12) . . ? C24C C23C H23C 119.8 . . ? C22C C23C H23C 119.8 . . ? C23C C24C C25C 121.1(10) . . ? C23C C24C Br1C 119.7(11) . . ? C25C C24C Br1C 119.1(9) . . ? C24C C25C C26C 119.9(10) . . ? C24C C25C H25C 120.1 . . ? C26C C25C H25C 120.1 . . ? C21C C26C C25C 118.6(11) . . ? C21C C26C H26C 120.7 . . ? C25C C26C H26C 120.7 . . ? C2C N3C N4C 115.5(5) . . ? C2C N3C H3C 122.3 . . ? N4C N3C H3C 122.3 . . ? C5C N4C N3C 116.9(6) . . ? C5C N4C Pr 125.0(5) . . ? N3C N4C Pr 117.5(4) . . ? N4C C5C C6C 117.0(6) . . ? N4C C5C H5C 121.5 . . ? C6C C5C H5C 121.5 . . ? N7C C6C C8C 123.0(7) . . ? N7C C6C C5C 116.5(6) . . ? C8C C6C C5C 120.5(7) . . ? C6C N7C C6D 116.9(5) . . ? C6C N7C Pr 122.1(4) . . ? C6D N7C Pr 121.0(4) . . ? C9C C8C C6C 119.6(7) . . ? C9C C8C H8C 120.2 . . ? C6C C8C H8C 120.2 . . ? C8C C9C C8D 118.1(7) . . ? C8C C9C H9C 120.9 . . ? C8D C9C H9C 120.9 . . ? C9C C8D C6D 119.4(7) . . ? C9C C8D H8D 120.3 . . ? C6D C8D H8D 120.3 . . ? N7C C6D C8D 122.8(6) . . ? N7C C6D C5D 116.2(5) . . ? C8D C6D C5D 121.0(6) . . ? N4D C5D C6D 118.6(6) . . ? N4D C5D H5D 120.7 . . ? C6D C5D H5D 120.7 . . ? C5D N4D N3D 116.8(5) . . ? C5D N4D Pr 124.2(4) . . ? N3D N4D Pr 117.7(4) . . ? C2D N3D N4D 116.0(5) . . ? C2D N3D H3D 122.0 . . ? N4D N3D H3D 122.0 . . ? O1D C2D N3D 120.8(6) . . ? O1D C2D C21D 122.4(6) . . ? N3D C2D C21D 116.8(6) . . ? C22D C21D C26D 119.0(6) . . ? C22D C21D C2D 123.2(6) . . ? C26D C21D C2D 117.7(6) . . ? C23D C22D C21D 120.5(7) . . ? C23D C22D H22D 119.7 . . ? C21D C22D H22D 119.7 . . ? C24D C23D C22D 118.8(7) . . ? C24D C23D H23D 120.6 . . ? C22D C23D H23D 120.6 . . ? C25D C24D C23D 121.9(7) . . ? C25D C24D Br1D 119.7(6) . . ? C23D C24D Br1D 118.4(6) . . ? C26D C25D C24D 119.2(8) . . ? C26D C25D H25D 120.4 . . ? C24D C25D H25D 120.4 . . ? C25D C26D C21D 120.5(7) . . ? C25D C26D H26D 119.7 . . ? C21D C26D H26D 119.7 . . ? C2D O1D Pr 125.6(4) . . ? O13A S1A O12A 115.5(3) . . ? O13A S1A O11A 116.2(3) . . ? O12A S1A O11A 113.8(3) . . ? O13A S1A C11A 103.1(4) . . ? O12A S1A C11A 103.1(4) . . ? O11A S1A C11A 102.5(3) . . ? S1A O11A Pr 141.4(3) . . ? F13A C11A F11A 107.8(7) . . ? F13A C11A F12A 109.0(8) . . ? F11A C11A F12A 105.7(7) . . ? F13A C11A S1A 111.6(6) . . ? F11A C11A S1A 111.6(6) . . ? F12A C11A S1A 110.9(6) . . ? O11B S1B O12B 114.8(4) . . ? O11B S1B O13B 117.0(4) . . ? O12B S1B O13B 114.7(4) . . ? O11B S1B C11B 102.0(5) . . ? O12B S1B C11B 101.9(5) . . ? O13B S1B C11B 103.4(6) . . ? F12B C11B F13B 104.4(11) . . ? F12B C11B F11B 111.5(11) . . ? F13B C11B F11B 107.9(11) . . ? F12B C11B S1B 112.6(10) . . ? F13B C11B S1B 112.9(9) . . ? F11B C11B S1B 107.5(9) . . ? O11C S1C O13C 115.1(10) . . ? O11C S1C O12C 116.1(9) . . ? O13C S1C O12C 114.6(9) . . ? O11C S1C C11C 103.1(8) . . ? O13C S1C C11C 103.3(9) . . ? O12C S1C C11C 101.9(9) . . ? F13C C11C F11C 107.2(14) . . ? F13C C11C F12C 107.9(15) . . ? F11C C11C F12C 108.1(16) . . ? F13C C11C S1C 110.4(11) . . ? F11C C11C S1C 110.6(13) . . ? F12C C11C S1C 112.5(15) . . ? O11D S1D O13D 116.0(8) . . ? O11D S1D O12D 114.6(8) . . ? O13D S1D O12D 114.7(9) . . ? O11D S1D C11D 104.3(8) . . ? O13D S1D C11D 103.1(9) . . ? O12D S1D C11D 101.4(8) . . ? F13D C11D F12D 106.1(15) . . ? F13D C11D F11D 106.6(16) . . ? F12D C11D F11D 107.9(15) . . ? F13D C11D S1D 109.8(14) . . ? F12D C11D S1D 113.6(13) . . ? F11D C11D S1D 112.4(13) . . ? 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 O1B Pr O1A C2A 160.7(5) . . . . ? O1C Pr O1A C2A 72.0(5) . . . . ? O1D Pr O1A C2A -62.8(5) . . . . ? N4D Pr O1A C2A -124.1(5) . . . . ? N4C Pr O1A C2A 123.8(5) . . . . ? N4A Pr O1A C2A 5.5(5) . . . . ? N7C Pr O1A C2A -171.0(5) . . . . ? N4B Pr O1A C2A 73.2(8) . . . . ? O11A Pr O1A C2A -75.0(5) . . . . ? N7A Pr O1A C2A 11.4(6) . . . . ? Pr O1A C2A N3A -5.3(9) . . . . ? Pr O1A C2A C21A 176.7(4) . . . . ? O1A C2A C21A C26A 161.0(7) . . . . ? N3A C2A C21A C26A -17.1(10) . . . . ? O1A C2A C21A C22A -15.5(10) . . . . ? N3A C2A C21A C22A 166.4(6) . . . . ? C26A C21A C22A C23A -1.8(12) . . . . ? C2A C21A C22A C23A 174.8(7) . . . . ? C21A C22A C23A C24A -0.5(13) . . . . ? C22A C23A C24A C25A 3.1(13) . . . . ? C22A C23A C24A Br1A -177.3(6) . . . . ? C23A C24A C25A C26A -3.3(12) . . . . ? Br1A C24A C25A C26A 177.1(6) . . . . ? C24A C25A C26A C21A 0.8(12) . . . . ? C22A C21A C26A C25A 1.6(12) . . . . ? C2A C21A C26A C25A -174.9(7) . . . . ? O1A C2A N3A N4A -0.6(9) . . . . ? C21A C2A N3A N4A 177.5(5) . . . . ? C2A N3A N4A C5A -177.3(6) . . . . ? C2A N3A N4A Pr 5.3(7) . . . . ? O1B Pr N4A C5A 77.8(7) . . . . ? O1C Pr N4A C5A 72.4(5) . . . . ? O1D Pr N4A C5A -50.4(5) . . . . ? O1A Pr N4A C5A 177.7(6) . . . . ? N4D Pr N4A C5A -102.7(5) . . . . ? N4C Pr N4A C5A 126.1(5) . . . . ? N7C Pr N4A C5A -178.4(5) . . . . ? N4B Pr N4A C5A 15.2(6) . . . . ? O11A Pr N4A C5A -111.1(6) . . . . ? N7A Pr N4A C5A 3.9(5) . . . . ? O1B Pr N4A N3A -105.0(5) . . . . ? O1C Pr N4A N3A -110.5(4) . . . . ? O1D Pr N4A N3A 126.8(4) . . . . ? O1A Pr N4A N3A -5.1(4) . . . . ? N4D Pr N4A N3A 74.5(5) . . . . ? N4C Pr N4A N3A -56.8(4) . . . . ? N7C Pr N4A N3A -1.3(5) . . . . ? N4B Pr N4A N3A -167.6(4) . . . . ? O11A Pr N4A N3A 66.0(4) . . . . ? N7A Pr N4A N3A -178.9(5) . . . . ? N3A N4A C5A C6A 178.9(6) . . . . ? Pr N4A C5A C6A -3.9(9) . . . . ? N4A C5A C6A N7A -0.1(10) . . . . ? N4A C5A C6A C8A -177.6(7) . . . . ? C8A C6A N7A C6B 0.8(11) . . . . ? C5A C6A N7A C6B -176.6(6) . . . . ? C8A C6A N7A Pr -178.9(6) . . . . ? C5A C6A N7A Pr 3.7(8) . . . . ? O1B Pr N7A C6A -161.6(5) . . . . ? O1C Pr N7A C6A -88.6(5) . . . . ? O1D Pr N7A C6A 110.6(5) . . . . ? O1A Pr N7A C6A -9.6(5) . . . . ? N4D Pr N7A C6A 116.7(5) . . . . ? N4C Pr N7A C6A -81.2(5) . . . . ? N4A Pr N7A C6A -3.8(5) . . . . ? N7C Pr N7A C6A -141(3) . . . . ? N4B Pr N7A C6A -171.5(6) . . . . ? O11A Pr N7A C6A 54.9(5) . . . . ? O1B Pr N7A C6B 18.8(5) . . . . ? O1C Pr N7A C6B 91.8(5) . . . . ? O1D Pr N7A C6B -69.1(5) . . . . ? O1A Pr N7A C6B 170.7(5) . . . . ? N4D Pr N7A C6B -62.9(5) . . . . ? N4C Pr N7A C6B 99.2(5) . . . . ? N4A Pr N7A C6B 176.6(6) . . . . ? N7C Pr N7A C6B 39(3) . . . . ? N4B Pr N7A C6B 8.8(5) . . . . ? O11A Pr N7A C6B -124.8(5) . . . . ? N7A C6A C8A C9A 2.3(14) . . . . ? C5A C6A C8A C9A 179.6(9) . . . . ? C6A C8A C9A C8B -2.9(17) . . . . ? C8A C9A C8B C6B 0.7(18) . . . . ? C6A N7A C6B C8B -3.2(11) . . . . ? Pr N7A C6B C8B 176.5(7) . . . . ? C6A N7A C6B C5B 172.5(7) . . . . ? Pr N7A C6B C5B -7.9(9) . . . . ? C9A C8B C6B N7A 2.5(16) . . . . ? C9A C8B C6B C5B -173.0(10) . . . . ? N7A C6B C5B N4B -1.9(12) . . . . ? C8B C6B C5B N4B 173.8(9) . . . . ? C6B C5B N4B N3B -173.8(7) . . . . ? C6B C5B N4B Pr 11.3(11) . . . . ? O1B Pr N4B C5B -179.7(7) . . . . ? O1C Pr N4B C5B -79.8(7) . . . . ? O1D Pr N4B C5B 61.5(6) . . . . ? O1A Pr N4B C5B -81.1(8) . . . . ? N4D Pr N4B C5B 115.8(7) . . . . ? N4C Pr N4B C5B -126.5(6) . . . . ? N4A Pr N4B C5B -21.7(7) . . . . ? N7C Pr N4B C5B 171.3(6) . . . . ? O11A Pr N4B C5B 60.5(7) . . . . ? N7A Pr N4B C5B -10.4(6) . . . . ? O1B Pr N4B N3B 5.3(5) . . . . ? O1C Pr N4B N3B 105.2(5) . . . . ? O1D Pr N4B N3B -113.5(5) . . . . ? O1A Pr N4B N3B 103.9(7) . . . . ? N4D Pr N4B N3B -59.2(5) . . . . ? N4C Pr N4B N3B 58.4(5) . . . . ? N4A Pr N4B N3B 163.3(5) . . . . ? N7C Pr N4B N3B -3.7(6) . . . . ? O11A Pr N4B N3B -114.5(5) . . . . ? N7A Pr N4B N3B 174.6(6) . . . . ? C5B N4B N3B C2B 177.7(7) . . . . ? Pr N4B N3B C2B -7.0(8) . . . . ? N4B N3B C2B O1B 4.0(10) . . . . ? N4B N3B C2B C21B -177.3(7) . . . . ? O1B C2B C21B C22B 3.1(11) . . . . ? N3B C2B C21B C22B -175.6(8) . . . . ? O1B C2B C21B C26B -174.8(8) . . . . ? N3B C2B C21B C26B 6.5(13) . . . . ? C26B C21B C22B C23B -1.9(14) . . . . ? C2B C21B C22B C23B -179.9(8) . . . . ? C21B C22B C23B C24B 1.6(14) . . . . ? C22B C23B C24B C25B 2.5(16) . . . . ? C22B C23B C24B Br1B -179.8(7) . . . . ? C23B C24B C25B C26B -6.1(17) . . . . ? Br1B C24B C25B C26B 176.3(8) . . . . ? C22B C21B C26B C25B -1.9(15) . . . . ? C2B C21B C26B C25B 176.0(9) . . . . ? C24B C25B C26B C21B 5.8(17) . . . . ? N3B C2B O1B Pr 1.8(10) . . . . ? C21B C2B O1B Pr -176.9(5) . . . . ? O1C Pr O1B C2B -71.9(6) . . . . ? O1D Pr O1B C2B 50.4(6) . . . . ? O1A Pr O1B C2B -163.4(5) . . . . ? N4D Pr O1B C2B 103.4(6) . . . . ? N4C Pr O1B C2B -129.1(6) . . . . ? N4A Pr O1B C2B -77.0(7) . . . . ? N7C Pr O1B C2B 167.3(6) . . . . ? N4B Pr O1B C2B -3.9(6) . . . . ? O11A Pr O1B C2B 114.2(6) . . . . ? N7A Pr O1B C2B -13.8(6) . . . . ? O1B Pr O1C C2C -77.6(6) . . . . ? O1D Pr O1C C2C -176.8(5) . . . . ? O1A Pr O1C C2C 45.4(6) . . . . ? N4D Pr O1C C2C -89.4(7) . . . . ? N4C Pr O1C C2C -9.5(5) . . . . ? N4A Pr O1C C2C 100.5(6) . . . . ? N7C Pr O1C C2C -19.5(6) . . . . ? N4B Pr O1C C2C -134.2(6) . . . . ? O11A Pr O1C C2C 95.4(6) . . . . ? N7A Pr O1C C2C 163.0(6) . . . . ? Pr O1C C2C N3C 7.7(10) . . . . ? Pr O1C C2C C21C -170.8(5) . . . . ? O1C C2C C21C C22C 8.3(11) . . . . ? N3C C2C C21C C22C -170.2(7) . . . . ? O1C C2C C21C C26C -172.0(8) . . . . ? N3C C2C C21C C26C 9.5(11) . . . . ? C26C C21C C22C C23C 2.2(14) . . . . ? C2C C21C C22C C23C -178.2(8) . . . . ? C21C C22C C23C C24C -3.0(16) . . . . ? C22C C23C C24C C25C 2.8(18) . . . . ? C22C C23C C24C Br1C 179.4(8) . . . . ? C23C C24C C25C C26C -1.8(18) . . . . ? Br1C C24C C25C C26C -178.4(8) . . . . ? C22C C21C C26C C25C -1.2(14) . . . . ? C2C C21C C26C C25C 179.2(9) . . . . ? C24C C25C C26C C21C 1.0(16) . . . . ? O1C C2C N3C N4C 3.4(10) . . . . ? C21C C2C N3C N4C -178.1(6) . . . . ? C2C N3C N4C C5C 177.0(7) . . . . ? C2C N3C N4C Pr -11.3(7) . . . . ? O1B Pr N4C C5C -79.3(6) . . . . ? O1C Pr N4C C5C -179.0(6) . . . . ? O1D Pr N4C C5C -82.1(11) . . . . ? O1A Pr N4C C5C 68.4(6) . . . . ? N4D Pr N4C C5C -23.4(6) . . . . ? N4A Pr N4C C5C 117.2(6) . . . . ? N7C Pr N4C C5C -9.7(6) . . . . ? N4B Pr N4C C5C -125.5(6) . . . . ? O11A Pr N4C C5C 48.2(6) . . . . ? N7A Pr N4C C5C 173.3(6) . . . . ? O1B Pr N4C N3C 109.7(5) . . . . ? O1C Pr N4C N3C 10.1(4) . . . . ? O1D Pr N4C N3C 106.9(8) . . . . ? O1A Pr N4C N3C -102.6(5) . . . . ? N4D Pr N4C N3C 165.6(4) . . . . ? N4A Pr N4C N3C -53.8(5) . . . . ? N7C Pr N4C N3C 179.4(5) . . . . ? N4B Pr N4C N3C 63.6(5) . . . . ? O11A Pr N4C N3C -122.7(4) . . . . ? N7A Pr N4C N3C 2.4(5) . . . . ? N3C N4C C5C C6C -178.8(6) . . . . ? Pr N4C C5C C6C 10.2(10) . . . . ? N4C C5C C6C N7C -1.6(11) . . . . ? N4C C5C C6C C8C 176.7(8) . . . . ? C8C C6C N7C C6D -3.7(11) . . . . ? C5C C6C N7C C6D 174.6(6) . . . . ? C8C C6C N7C Pr 174.4(6) . . . . ? C5C C6C N7C Pr -7.4(9) . . . . ? O1B Pr N7C C6C 90.7(5) . . . . ? O1C Pr N7C C6C 18.4(6) . . . . ? O1D Pr N7C C6C 176.7(5) . . . . ? O1A Pr N7C C6C -62.7(5) . . . . ? N4D Pr N7C C6C 173.7(6) . . . . ? N4C Pr N7C C6C 8.3(5) . . . . ? N4A Pr N7C C6C -66.3(6) . . . . ? N4B Pr N7C C6C 99.3(5) . . . . ? O11A Pr N7C C6C -126.1(5) . . . . ? N7A Pr N7C C6C 70(3) . . . . ? O1B Pr N7C C6D -91.3(5) . . . . ? O1C Pr N7C C6D -163.6(4) . . . . ? O1D Pr N7C C6D -5.4(5) . . . . ? O1A Pr N7C C6D 115.3(5) . . . . ? N4D Pr N7C C6D -8.3(4) . . . . ? N4C Pr N7C C6D -173.7(5) . . . . ? N4A Pr N7C C6D 111.7(5) . . . . ? N4B Pr N7C C6D -82.7(5) . . . . ? O11A Pr N7C C6D 51.9(5) . . . . ? N7A Pr N7C C6D -112(3) . . . . ? N7C C6C C8C C9C 2.0(14) . . . . ? C5C C6C C8C C9C -176.2(9) . . . . ? C6C C8C C9C C8D 0.6(15) . . . . ? C8C C9C C8D C6D -1.3(14) . . . . ? C6C N7C C6D C8D 2.9(10) . . . . ? Pr N7C C6D C8D -175.2(5) . . . . ? C6C N7C C6D C5D -175.3(6) . . . . ? Pr N7C C6D C5D 6.6(8) . . . . ? C9C C8D C6D N7C -0.5(12) . . . . ? C9C C8D C6D C5D 177.7(8) . . . . ? N7C C6D C5D N4D 3.1(9) . . . . ? C8D C6D C5D N4D -175.2(7) . . . . ? C6D C5D N4D N3D -178.9(6) . . . . ? C6D C5D N4D Pr -12.0(9) . . . . ? O1B Pr N4D C5D 79.8(5) . . . . ? O1C Pr N4D C5D 92.3(6) . . . . ? O1D Pr N4D C5D -166.5(6) . . . . ? O1A Pr N4D C5D -41.0(5) . . . . ? N4C Pr N4D C5D 24.2(6) . . . . ? N4A Pr N4D C5D -100.0(5) . . . . ? N7C Pr N4D C5D 10.5(5) . . . . ? N4B Pr N4D C5D 133.9(5) . . . . ? O11A Pr N4D C5D -91.1(5) . . . . ? N7A Pr N4D C5D -172.8(5) . . . . ? O1B Pr N4D N3D -113.4(4) . . . . ? O1C Pr N4D N3D -100.8(5) . . . . ? O1D Pr N4D N3D 0.4(4) . . . . ? O1A Pr N4D N3D 125.8(4) . . . . ? N4C Pr N4D N3D -168.9(4) . . . . ? N4A Pr N4D N3D 66.8(5) . . . . ? N7C Pr N4D N3D 177.3(5) . . . . ? N4B Pr N4D N3D -59.2(4) . . . . ? O11A Pr N4D N3D 75.7(4) . . . . ? N7A Pr N4D N3D -6.0(5) . . . . ? C5D N4D N3D C2D 163.5(6) . . . . ? Pr N4D N3D C2D -4.3(7) . . . . ? N4D N3D C2D O1D 8.3(9) . . . . ? N4D N3D C2D C21D -171.2(5) . . . . ? O1D C2D C21D C22D -168.4(7) . . . . ? N3D C2D C21D C22D 11.1(10) . . . . ? O1D C2D C21D C26D 9.2(10) . . . . ? N3D C2D C21D C26D -171.2(6) . . . . ? C26D C21D C22D C23D 0.5(11) . . . . ? C2D C21D C22D C23D 178.2(7) . . . . ? C21D C22D C23D C24D 0.6(13) . . . . ? C22D C23D C24D C25D -1.0(14) . . . . ? C22D C23D C24D Br1D -178.7(6) . . . . ? C23D C24D C25D C26D 0.2(14) . . . . ? Br1D C24D C25D C26D 177.9(7) . . . . ? C24D C25D C26D C21D 1.0(13) . . . . ? C22D C21D C26D C25D -1.4(12) . . . . ? C2D C21D C26D C25D -179.2(7) . . . . ? N3D C2D O1D Pr -8.8(9) . . . . ? C21D C2D O1D Pr 170.8(4) . . . . ? O1B Pr O1D C2D 65.4(5) . . . . ? O1C Pr O1D C2D 158.2(5) . . . . ? O1A Pr O1D C2D -78.9(5) . . . . ? N4D Pr O1D C2D 4.3(5) . . . . ? N4C Pr O1D C2D 68.0(10) . . . . ? N4A Pr O1D C2D -131.2(5) . . . . ? N7C Pr O1D C2D 1.4(6) . . . . ? N4B Pr O1D C2D 114.2(5) . . . . ? O11A Pr O1D C2D -66.7(5) . . . . ? N7A Pr O1D C2D 178.3(6) . . . . ? O13A S1A O11A Pr -29.6(6) . . . . ? O12A S1A O11A Pr 108.1(4) . . . . ? C11A S1A O11A Pr -141.2(4) . . . . ? O1B Pr O11A S1A 67.5(5) . . . . ? O1C Pr O11A S1A -103.0(4) . . . . ? O1D Pr O11A S1A 146.5(5) . . . . ? O1A Pr O11A S1A -44.3(4) . . . . ? N4D Pr O11A S1A 79.1(4) . . . . ? N4C Pr O11A S1A -24.4(5) . . . . ? N4A Pr O11A S1A -108.2(4) . . . . ? N7C Pr O11A S1A 21.9(4) . . . . ? N4B Pr O11A S1A 147.6(4) . . . . ? N7A Pr O11A S1A -158.9(4) . . . . ? O13A S1A C11A F13A -179.8(7) . . . . ? O12A S1A C11A F13A 59.7(7) . . . . ? O11A S1A C11A F13A -58.7(7) . . . . ? O13A S1A C11A F11A 59.6(6) . . . . ? O12A S1A C11A F11A -61.0(6) . . . . ? O11A S1A C11A F11A -179.4(6) . . . . ? O13A S1A C11A F12A -58.1(7) . . . . ? O12A S1A C11A F12A -178.6(6) . . . . ? O11A S1A C11A F12A 63.0(7) . . . . ? O11B S1B C11B F12B 61.9(10) . . . . ? O12B S1B C11B F12B -179.3(9) . . . . ? O13B S1B C11B F12B -60.0(11) . . . . ? O11B S1B C11B F13B 179.7(9) . . . . ? O12B S1B C11B F13B -61.4(10) . . . . ? O13B S1B C11B F13B 57.9(10) . . . . ? O11B S1B C11B F11B -61.3(9) . . . . ? O12B S1B C11B F11B 57.6(9) . . . . ? O13B S1B C11B F11B 176.8(8) . . . . ? O11C S1C C11C F13C -56.4(14) . . . . ? O13C S1C C11C F13C -176.5(12) . . . . ? O12C S1C C11C F13C 64.4(13) . . . . ? O11C S1C C11C F11C 62.0(14) . . . . ? O13C S1C C11C F11C -58.1(15) . . . . ? O12C S1C C11C F11C -177.3(13) . . . . ? O11C S1C C11C F12C -176.9(15) . . . . ? O13C S1C C11C F12C 62.9(16) . . . . ? O12C S1C C11C F12C -56.2(16) . . . . ? O11D S1D C11D F13D 60.3(15) . . . . ? O13D S1D C11D F13D -178.1(14) . . . . ? O12D S1D C11D F13D -59.1(15) . . . . ? O11D S1D C11D F12D 178.9(13) . . . . ? O13D S1D C11D F12D -59.5(15) . . . . ? O12D S1D C11D F12D 59.5(15) . . . . ? O11D S1D C11D F11D -58.2(16) . . . . ? O13D S1D C11D F11D 63.4(16) . . . . ? O12D S1D C11D F11D -177.6(14) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 3.523 _refine_diff_density_min -2.262 _refine_diff_density_rms 0.196 # Attachment 'fro4513.cif' data_fro4513 _database_code_depnum_ccdc_archive 'CCDC 728922' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C54 H56 Br4 F9 La N10 O17 S3' _chemical_formula_weight 1842.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 20.6299(4) _cell_length_b 16.7038(4) _cell_length_c 21.2816(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.985(1) _cell_angle_gamma 90.00 _cell_volume 7116.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 12242 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.720 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3648 _exptl_absorpt_coefficient_mu 3.028 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4636 _exptl_absorpt_correction_T_max 0.8634 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 45951 _diffrn_reflns_av_R_equivalents 0.098 _diffrn_reflns_av_sigmaI/netI 0.0908 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.00 _reflns_number_total 12499 _reflns_number_gt 7607 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Hydrogen atoms at methanol (O201-C202) fixed, ether molecules refined with geometrical restraints (DFIX), for all anions and solvents molecules thermal restraints are used (ISOR). ; _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^)+(0.0740P)^2^+50.1277P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at O301 from difmap, others geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12499 _refine_ls_number_parameters 889 _refine_ls_number_restraints 252 _refine_ls_R_factor_all 0.1425 _refine_ls_R_factor_gt 0.0806 _refine_ls_wR_factor_ref 0.2025 _refine_ls_wR_factor_gt 0.1741 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.005 _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 La La 0.67066(3) -0.24421(3) -0.18490(2) 0.03524(17) Uani 1 1 d . . . O1A O 0.6458(3) -0.1334(4) -0.1089(3) 0.0483(17) Uani 1 1 d U . . C2A C 0.6076(5) -0.0758(6) -0.1230(5) 0.046(2) Uani 1 1 d . . . C21A C 0.5950(5) -0.0205(5) -0.0733(4) 0.042(2) Uani 1 1 d . . . C22A C 0.6390(6) -0.0203(6) -0.0123(5) 0.056(3) Uani 1 1 d . . . H22A H 0.6754 -0.0559 -0.0041 0.067 Uiso 1 1 calc R . . C23A C 0.6309(7) 0.0304(7) 0.0368(6) 0.068(3) Uani 1 1 d . . . H23A H 0.6610 0.0298 0.0778 0.081 Uiso 1 1 calc R . . C24A C 0.5771(7) 0.0820(6) 0.0234(5) 0.060(3) Uani 1 1 d . . . C25A C 0.5311(6) 0.0814(6) -0.0356(5) 0.061(3) Uani 1 1 d . . . H25A H 0.4940 0.1157 -0.0431 0.074 Uiso 1 1 calc R . . C26A C 0.5401(6) 0.0295(6) -0.0843(5) 0.056(3) Uani 1 1 d . . . H26A H 0.5088 0.0287 -0.1245 0.068 Uiso 1 1 calc R . . Br1A Br 0.56343(9) 0.15319(7) 0.08837(6) 0.0843(5) Uani 1 1 d . . . N3A N 0.5772(4) -0.0612(5) -0.1853(4) 0.044(2) Uani 1 1 d . . . H3A H 0.5501 -0.0210 -0.1965 0.053 Uiso 1 1 calc R . . N4A N 0.5913(4) -0.1130(4) -0.2308(4) 0.0418(19) Uani 1 1 d . . . C5A C 0.5610(5) -0.1031(6) -0.2898(5) 0.048(3) Uani 1 1 d . . . H5A H 0.5307 -0.0607 -0.3023 0.057 Uiso 1 1 calc R . . C6A C 0.5744(5) -0.1599(5) -0.3381(4) 0.039(2) Uani 1 1 d . . . N7A N 0.6221(4) -0.2146(5) -0.3166(3) 0.0414(19) Uani 1 1 d . . . C8A C 0.5381(5) -0.1575(6) -0.4014(5) 0.050(3) Uani 1 1 d . . . H8A H 0.5050 -0.1182 -0.4144 0.060 Uiso 1 1 calc R . . C9A C 0.5498(6) -0.2121(7) -0.4461(5) 0.053(3) Uani 1 1 d . . . H9A H 0.5242 -0.2131 -0.4891 0.064 Uiso 1 1 calc R . . C8B C 0.6021(5) -0.2658(6) -0.4235(5) 0.051(3) Uani 1 1 d . . . H8B H 0.6135 -0.3028 -0.4523 0.061 Uiso 1 1 calc R . . C6B C 0.6363(5) -0.2655(5) -0.3613(4) 0.043(2) Uani 1 1 d . . . C5B C 0.6927(5) -0.3212(6) -0.3368(5) 0.049(3) Uani 1 1 d . . . H5B H 0.7061 -0.3574 -0.3651 0.058 Uiso 1 1 calc R . . N4B N 0.7229(4) -0.3195(4) -0.2769(4) 0.0400(19) Uani 1 1 d . . . N3B N 0.7725(4) -0.3744(5) -0.2554(4) 0.051(2) Uani 1 1 d . . . H3B H 0.7873 -0.4046 -0.2822 0.061 Uiso 1 1 calc R . . C2B C 0.7974(5) -0.3796(6) -0.1911(5) 0.047(3) Uani 1 1 d . . . C21B C 0.8502(5) -0.4395(6) -0.1662(5) 0.050(3) Uani 1 1 d . . . C22B C 0.8832(6) -0.4815(8) -0.2046(6) 0.072(4) Uani 1 1 d . . . H22B H 0.8716 -0.4730 -0.2496 0.086 Uiso 1 1 calc R . . C23B C 0.9328(7) -0.5359(8) -0.1788(7) 0.080(4) Uani 1 1 d . . . H23B H 0.9545 -0.5644 -0.2058 0.095 Uiso 1 1 calc R . . C24B C 0.9496(7) -0.5475(8) -0.1148(7) 0.080(4) Uani 1 1 d . . . C25B C 0.9171(7) -0.5089(9) -0.0740(7) 0.093(5) Uani 1 1 d . . . H25B H 0.9273 -0.5204 -0.0294 0.112 Uiso 1 1 calc R . . C26B C 0.8687(6) -0.4520(8) -0.1010(6) 0.076(4) Uani 1 1 d . . . H26B H 0.8484 -0.4218 -0.0737 0.091 Uiso 1 1 calc R . . Br1B Br 1.02102(11) -0.61823(12) -0.07798(10) 0.1376(9) Uani 1 1 d . . . O1B O 0.7750(3) -0.3357(4) -0.1538(3) 0.0469(17) Uani 1 1 d U . . O1C O 0.5447(3) -0.2648(4) -0.2280(3) 0.0481(17) Uani 1 1 d U . . C2C C 0.5067(5) -0.3064(5) -0.2055(5) 0.043(2) Uani 1 1 d . . . C21C C 0.4401(5) -0.3282(6) -0.2440(5) 0.042(2) Uani 1 1 d . . . C22C C 0.3960(6) -0.3786(7) -0.2220(5) 0.063(3) Uani 1 1 d . . . H22C H 0.4067 -0.3949 -0.1784 0.075 Uiso 1 1 calc R . . C23C C 0.3363(6) -0.4053(7) -0.2632(6) 0.065(3) Uani 1 1 d . . . H23C H 0.3065 -0.4377 -0.2474 0.078 Uiso 1 1 calc R . . C24C C 0.3226(5) -0.3832(6) -0.3265(5) 0.054(3) Uani 1 1 d . . . C25C C 0.3650(6) -0.3318(7) -0.3493(6) 0.064(3) Uani 1 1 d . . . H25C H 0.3539 -0.3153 -0.3928 0.077 Uiso 1 1 calc R . . C26C C 0.4226(6) -0.3055(6) -0.3086(5) 0.056(3) Uani 1 1 d . . . H26C H 0.4510 -0.2712 -0.3246 0.067 Uiso 1 1 calc R . . Br1C Br 0.24668(7) -0.42555(9) -0.38519(7) 0.0781(4) Uani 1 1 d . . . N3C N 0.5273(4) -0.3356(5) -0.1445(4) 0.0426(19) Uani 1 1 d . . . H3C H 0.5016 -0.3646 -0.1267 0.051 Uiso 1 1 calc R . . N4C N 0.5925(4) -0.3159(5) -0.1125(4) 0.043(2) Uani 1 1 d . . . C5C C 0.6175(5) -0.3528(5) -0.0590(4) 0.041(2) Uani 1 1 d . . . H5C H 0.5935 -0.3925 -0.0430 0.049 Uiso 1 1 calc R . . C6C C 0.6852(5) -0.3299(5) -0.0243(4) 0.039(2) Uani 1 1 d . . . N7C N 0.7171(4) -0.2764(4) -0.0540(3) 0.0360(18) Uani 1 1 d . . . C8C C 0.7127(6) -0.3580(6) 0.0385(5) 0.054(3) Uani 1 1 d . . . H8C H 0.6898 -0.3956 0.0580 0.065 Uiso 1 1 calc R . . C9C C 0.7731(6) -0.3297(7) 0.0703(6) 0.067(3) Uani 1 1 d . . . H9C H 0.7932 -0.3496 0.1117 0.080 Uiso 1 1 calc R . . C8D C 0.8060(6) -0.2717(7) 0.0429(5) 0.058(3) Uani 1 1 d . . . H8D H 0.8468 -0.2498 0.0659 0.070 Uiso 1 1 calc R . . C6D C 0.7760(5) -0.2473(6) -0.0203(4) 0.045(2) Uani 1 1 d . . . C5D C 0.8097(5) -0.1888(6) -0.0517(5) 0.050(3) Uani 1 1 d . . . H5D H 0.8490 -0.1633 -0.0291 0.060 Uiso 1 1 calc R . . N4D N 0.7838(4) -0.1733(4) -0.1113(4) 0.0423(19) Uani 1 1 d . . . N3D N 0.8163(4) -0.1182(5) -0.1418(4) 0.045(2) Uani 1 1 d . . . H3D H 0.8520 -0.0929 -0.1213 0.054 Uiso 1 1 calc R . . C2D C 0.7885(5) -0.1066(5) -0.2056(5) 0.039(2) Uani 1 1 d . . . C21D C 0.8222(5) -0.0513(6) -0.2413(5) 0.045(2) Uani 1 1 d . . . C22D C 0.8872(6) -0.0255(7) -0.2198(5) 0.061(3) Uani 1 1 d . . . H22D H 0.9117 -0.0418 -0.1786 0.074 Uiso 1 1 calc R . . C23D C 0.9183(6) 0.0244(8) -0.2571(6) 0.073(4) Uani 1 1 d . . . H23D H 0.9626 0.0420 -0.2421 0.088 Uiso 1 1 calc R . . C24D C 0.8792(7) 0.0458(7) -0.3176(6) 0.068(3) Uani 1 1 d . . . C25D C 0.8155(6) 0.0226(7) -0.3398(5) 0.059(3) Uani 1 1 d . . . H25D H 0.7909 0.0390 -0.3809 0.071 Uiso 1 1 calc R . . C26D C 0.7864(5) -0.0257(6) -0.3013(5) 0.049(3) Uani 1 1 d . . . H26D H 0.7416 -0.0413 -0.3164 0.058 Uiso 1 1 calc R . . Br1D Br 0.91918(10) 0.11127(12) -0.37076(9) 0.1200(7) Uani 1 1 d . . . O1D O 0.7369(3) -0.1417(4) -0.2327(3) 0.0468(17) Uani 1 1 d U . . S1A S 0.60636(14) -0.46040(14) -0.25002(12) 0.0444(6) Uani 1 1 d . . . O11A O 0.6397(3) -0.3958(4) -0.2095(3) 0.0463(16) Uani 1 1 d U . . O12A O 0.5379(4) -0.4708(4) -0.2484(4) 0.0586(19) Uani 1 1 d U . . O13A O 0.6183(4) -0.4638(5) -0.3132(4) 0.072(2) Uani 1 1 d U . . C11A C 0.6477(9) -0.5471(8) -0.2067(8) 0.088(4) Uani 1 1 d . . . F11A F 0.7119(6) -0.5475(6) -0.2040(6) 0.135(3) Uani 1 1 d U . . F12A F 0.6394(6) -0.5505(6) -0.1486(5) 0.138(4) Uani 1 1 d U . . F13A F 0.6208(5) -0.6146(5) -0.2351(5) 0.116(3) Uani 1 1 d U . . S1B S 0.40136(14) -0.06179(15) 0.45762(12) 0.0485(7) Uani 1 1 d . . . O11B O 0.3647(4) -0.0131(5) 0.4059(4) 0.067(2) Uani 1 1 d U . . O12B O 0.4232(4) -0.0235(4) 0.5197(3) 0.063(2) Uani 1 1 d U . . O13B O 0.4513(4) -0.1113(4) 0.4399(3) 0.0524(18) Uani 1 1 d U . . C11B C 0.3403(6) -0.1330(8) 0.4702(6) 0.071(4) Uani 1 1 d . . . F11B F 0.3674(4) -0.1855(5) 0.5169(4) 0.103(3) Uani 1 1 d U . . F12B F 0.2906(4) -0.0967(6) 0.4890(4) 0.109(3) Uani 1 1 d U . . F13B F 0.3130(5) -0.1745(5) 0.4173(5) 0.113(3) Uani 1 1 d U . . S1C S 0.1569(3) 0.0228(3) -0.1043(2) 0.1020(14) Uani 1 1 d . . . O11C O 0.0923(8) 0.0376(10) -0.1422(8) 0.168(5) Uani 1 1 d U . . O12C O 0.1718(8) 0.0436(9) -0.0378(7) 0.162(5) Uani 1 1 d U . . O13C O 0.2098(6) 0.0382(7) -0.1353(5) 0.115(4) Uani 1 1 d U . . C11C C 0.1626(14) -0.0868(18) -0.0949(13) 0.163(10) Uani 1 1 d . . . F11C F 0.1181(8) -0.1084(9) -0.0634(7) 0.204(6) Uani 1 1 d U . . F12C F 0.1413(10) -0.1143(10) -0.1544(9) 0.220(7) Uani 1 1 d U . . F13C F 0.2186(10) -0.1090(10) -0.0648(9) 0.214(7) Uani 1 1 d U . . C101 C 0.8227(13) 0.2236(15) -0.2576(9) 0.211(12) Uani 1 1 d DU . . H10A H 0.8522 0.2526 -0.2789 0.316 Uiso 1 1 calc R . . H10B H 0.7849 0.2030 -0.2900 0.316 Uiso 1 1 calc R . . H10C H 0.8469 0.1794 -0.2331 0.316 Uiso 1 1 calc R . . C102 C 0.7982(10) 0.2790(13) -0.2127(7) 0.164(9) Uani 1 1 d DU . . H10D H 0.8059 0.3346 -0.2237 0.196 Uiso 1 1 calc R . . H10E H 0.7501 0.2715 -0.2181 0.196 Uiso 1 1 calc R . . O103 O 0.8321(6) 0.2637(8) -0.1472(6) 0.137(4) Uani 1 1 d DU . . C104 C 0.8030(8) 0.3079(10) -0.1037(7) 0.126(6) Uani 1 1 d DU . . H10F H 0.7556 0.2937 -0.1108 0.151 Uiso 1 1 calc R . . H10G H 0.8060 0.3653 -0.1119 0.151 Uiso 1 1 calc R . . C105 C 0.8388(10) 0.2894(13) -0.0347(7) 0.154(8) Uani 1 1 d DU . . H10H H 0.8256 0.2368 -0.0230 0.230 Uiso 1 1 calc R . . H10I H 0.8273 0.3293 -0.0061 0.230 Uiso 1 1 calc R . . H10J H 0.8867 0.2902 -0.0306 0.230 Uiso 1 1 calc R . . C111 C 0.9076(13) -0.2544(16) -0.2950(10) 0.202(11) Uani 1 1 d DU . . H11A H 0.8729 -0.2847 -0.2820 0.303 Uiso 1 1 calc R . . H11B H 0.9288 -0.2879 -0.3214 0.303 Uiso 1 1 calc R . . H11C H 0.8880 -0.2079 -0.3197 0.303 Uiso 1 1 calc R . . C112 C 0.9586(12) -0.228(2) -0.2359(10) 0.263(17) Uani 1 1 d DU . . H11D H 0.9991 -0.2603 -0.2309 0.315 Uiso 1 1 calc R . . H11E H 0.9706 -0.1718 -0.2411 0.315 Uiso 1 1 calc R . . O113 O 0.9334(9) -0.2355(13) -0.1797(9) 0.232(9) Uani 1 1 d DU . . C114 C 0.9810(14) -0.2066(19) -0.1240(11) 0.280(17) Uani 1 1 d DU . . H11F H 0.9776 -0.1482 -0.1221 0.336 Uiso 1 1 calc R . . H11G H 1.0261 -0.2198 -0.1280 0.336 Uiso 1 1 calc R . . C115 C 0.9704(16) -0.2420(19) -0.0625(11) 0.254(16) Uani 1 1 d DU . . H11H H 1.0068 -0.2263 -0.0266 0.382 Uiso 1 1 calc R . . H11I H 0.9690 -0.2999 -0.0661 0.382 Uiso 1 1 calc R . . H11J H 0.9285 -0.2227 -0.0552 0.382 Uiso 1 1 calc R . . O201 O 0.9265(13) 0.1402(15) -0.0974(12) 0.264(10) Uani 1 1 d U . . H201 H 0.9081 0.1348 -0.1364 0.395 Uiso 1 1 calc R . . C202 C 0.995(3) 0.143(4) -0.090(3) 0.49(4) Uani 1 1 d U . . H20A H 1.0053 0.1783 -0.1222 0.742 Uiso 1 1 calc R . . H20B H 1.0118 0.0900 -0.0940 0.742 Uiso 1 1 calc R . . H20C H 1.0156 0.1641 -0.0468 0.742 Uiso 1 1 calc R . . O301 O 0.9053(6) -0.0197(8) -0.0589(7) 0.118(4) Uani 1 1 d DU . . H30A H 0.929(7) -0.060(6) -0.059(11) 0.177 Uiso 1 1 d D . . H30B H 0.927(7) 0.022(6) -0.047(10) 0.177 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 La 0.0455(3) 0.0333(3) 0.0283(3) 0.0011(2) 0.0115(2) -0.0008(3) O1A 0.060(4) 0.047(4) 0.038(4) -0.005(3) 0.012(3) 0.006(4) C2A 0.059(7) 0.035(5) 0.047(6) 0.000(5) 0.022(5) 0.006(5) C21A 0.062(7) 0.037(5) 0.030(5) 0.004(4) 0.014(5) 0.000(5) C22A 0.069(8) 0.048(6) 0.053(7) 0.000(5) 0.020(6) 0.008(6) C23A 0.099(10) 0.061(7) 0.043(7) 0.001(6) 0.017(7) -0.002(8) C24A 0.100(10) 0.038(6) 0.049(7) -0.010(5) 0.033(7) -0.001(6) C25A 0.089(9) 0.045(6) 0.052(7) -0.002(5) 0.021(7) 0.026(6) C26A 0.072(8) 0.048(6) 0.050(7) -0.005(5) 0.015(6) 0.015(6) Br1A 0.1474(14) 0.0540(7) 0.0587(8) -0.0143(6) 0.0388(8) 0.0090(8) N3A 0.058(5) 0.043(5) 0.029(5) 0.004(4) 0.007(4) 0.012(4) N4A 0.056(5) 0.038(4) 0.030(5) -0.002(3) 0.010(4) 0.005(4) C5A 0.057(7) 0.043(6) 0.046(7) 0.007(5) 0.017(5) 0.010(5) C6A 0.047(6) 0.041(5) 0.029(5) 0.007(4) 0.013(5) -0.002(5) N7A 0.053(5) 0.046(5) 0.028(4) 0.001(4) 0.014(4) 0.000(4) C8A 0.057(7) 0.053(6) 0.038(6) 0.010(5) 0.009(5) 0.001(5) C9A 0.063(7) 0.069(7) 0.027(6) 0.006(5) 0.011(5) -0.008(6) C8B 0.070(7) 0.054(6) 0.031(6) 0.001(5) 0.017(5) 0.000(6) C6B 0.057(6) 0.041(5) 0.035(5) 0.009(4) 0.020(5) 0.001(5) C5B 0.065(7) 0.044(6) 0.044(7) 0.001(5) 0.026(6) 0.001(5) N4B 0.053(5) 0.036(4) 0.032(5) 0.005(3) 0.013(4) 0.001(4) N3B 0.074(6) 0.045(5) 0.040(5) 0.002(4) 0.025(5) 0.018(5) C2B 0.057(7) 0.040(6) 0.047(7) -0.003(5) 0.016(5) -0.003(5) C21B 0.052(7) 0.047(6) 0.045(6) -0.002(5) 0.003(5) 0.003(5) C22B 0.077(9) 0.082(9) 0.054(7) -0.010(6) 0.011(7) 0.034(7) C23B 0.081(10) 0.087(9) 0.068(9) -0.016(7) 0.014(7) 0.030(8) C24B 0.079(9) 0.066(8) 0.083(10) -0.015(7) -0.005(8) 0.038(7) C25B 0.102(11) 0.093(10) 0.064(9) 0.003(8) -0.019(8) 0.032(9) C26B 0.084(9) 0.077(8) 0.054(8) -0.012(6) -0.005(7) 0.039(8) Br1B 0.1432(17) 0.1144(14) 0.1251(15) -0.0160(11) -0.0265(13) 0.0799(13) O1B 0.050(4) 0.045(4) 0.043(4) -0.007(3) 0.006(3) 0.006(3) O1C 0.056(4) 0.049(4) 0.041(4) 0.013(3) 0.015(3) -0.009(3) C2C 0.056(7) 0.035(5) 0.041(6) -0.004(4) 0.018(5) -0.002(5) C21C 0.047(6) 0.042(5) 0.040(6) -0.002(4) 0.016(5) 0.001(5) C22C 0.082(9) 0.072(8) 0.043(7) 0.007(6) 0.033(6) -0.017(7) C23C 0.062(8) 0.082(8) 0.050(7) -0.003(6) 0.012(6) -0.030(7) C24C 0.044(6) 0.057(7) 0.057(8) -0.006(5) 0.006(5) -0.001(6) C25C 0.065(8) 0.080(8) 0.047(7) 0.016(6) 0.013(6) -0.012(7) C26C 0.061(7) 0.056(7) 0.046(7) 0.009(5) 0.005(6) -0.010(6) Br1C 0.0719(9) 0.0845(9) 0.0684(9) -0.0001(7) -0.0018(7) -0.0177(7) N3C 0.051(5) 0.045(5) 0.035(5) -0.001(4) 0.018(4) -0.013(4) N4C 0.053(5) 0.047(5) 0.032(5) -0.001(4) 0.017(4) 0.000(4) C5C 0.054(6) 0.038(5) 0.034(6) -0.004(4) 0.019(5) 0.004(5) C6C 0.053(6) 0.041(5) 0.028(5) -0.001(4) 0.016(5) 0.006(5) N7C 0.043(5) 0.033(4) 0.034(4) 0.001(3) 0.012(4) 0.000(4) C8C 0.068(8) 0.054(6) 0.043(6) 0.015(5) 0.016(6) 0.001(6) C9C 0.065(8) 0.072(8) 0.056(7) 0.022(6) -0.001(6) -0.002(7) C8D 0.059(7) 0.071(8) 0.043(6) 0.009(5) 0.008(5) 0.000(6) C6D 0.058(6) 0.049(6) 0.032(5) 0.010(5) 0.015(5) 0.003(6) C5D 0.052(7) 0.053(6) 0.042(6) 0.002(5) 0.004(5) -0.004(5) N4D 0.054(5) 0.033(4) 0.040(5) 0.000(4) 0.011(4) -0.005(4) N3D 0.043(5) 0.050(5) 0.039(5) 0.001(4) 0.006(4) -0.009(4) C2D 0.048(6) 0.038(5) 0.033(6) 0.007(4) 0.011(5) 0.006(5) C21D 0.052(7) 0.041(5) 0.042(6) -0.001(4) 0.013(5) -0.007(5) C22D 0.070(8) 0.071(8) 0.045(7) 0.011(6) 0.018(6) -0.008(7) C23D 0.063(8) 0.088(9) 0.068(9) 0.013(7) 0.013(7) -0.024(7) C24D 0.080(9) 0.066(8) 0.069(9) 0.016(6) 0.038(8) -0.011(7) C25D 0.073(9) 0.064(7) 0.044(6) 0.019(5) 0.024(6) 0.006(7) C26D 0.056(7) 0.047(6) 0.045(6) -0.001(5) 0.018(5) 0.004(5) Br1D 0.1358(15) 0.1243(14) 0.1132(14) 0.0513(11) 0.0561(12) -0.0331(12) O1D 0.049(4) 0.047(4) 0.043(4) 0.005(3) 0.010(3) -0.010(3) S1A 0.0610(17) 0.0369(13) 0.0370(14) -0.0048(10) 0.0151(12) -0.0066(12) O11A 0.057(4) 0.044(4) 0.041(4) -0.005(3) 0.017(3) -0.005(3) O12A 0.064(5) 0.053(4) 0.062(4) -0.009(3) 0.019(4) -0.010(4) O13A 0.104(6) 0.068(5) 0.052(4) -0.015(4) 0.037(4) -0.026(4) C11A 0.111(13) 0.046(8) 0.100(12) 0.011(7) 0.015(10) -0.020(8) F11A 0.112(6) 0.099(6) 0.183(8) 0.010(6) 0.013(6) 0.018(5) F12A 0.185(8) 0.119(6) 0.100(6) 0.049(5) 0.014(6) -0.008(6) F13A 0.144(6) 0.054(4) 0.141(6) 0.001(4) 0.018(5) 0.001(4) S1B 0.0612(17) 0.0469(14) 0.0401(15) 0.0002(12) 0.0177(13) 0.0084(13) O11B 0.076(5) 0.072(5) 0.052(4) 0.005(4) 0.015(4) 0.018(4) O12B 0.085(5) 0.058(4) 0.050(4) -0.015(3) 0.021(4) 0.008(4) O13B 0.062(4) 0.055(4) 0.042(4) -0.005(3) 0.016(3) 0.012(3) C11B 0.063(8) 0.092(10) 0.061(8) 0.023(7) 0.022(7) 0.011(7) F11B 0.108(5) 0.103(5) 0.099(5) 0.041(4) 0.029(4) -0.012(4) F12B 0.084(5) 0.141(6) 0.116(6) 0.021(5) 0.053(5) 0.006(5) F13B 0.115(6) 0.106(6) 0.105(6) -0.004(5) 0.001(5) -0.034(5) S1C 0.138(4) 0.115(3) 0.064(2) 0.001(2) 0.047(3) -0.022(3) O11C 0.151(9) 0.197(10) 0.167(9) 0.027(8) 0.061(8) 0.033(8) O12C 0.202(9) 0.157(9) 0.135(8) -0.023(7) 0.056(7) 0.002(7) O13C 0.125(7) 0.135(7) 0.090(6) 0.027(5) 0.035(5) -0.046(6) C11C 0.15(2) 0.22(3) 0.115(19) 0.015(18) 0.025(16) -0.08(2) F11C 0.224(10) 0.203(9) 0.194(9) 0.034(8) 0.069(8) -0.052(8) F12C 0.257(11) 0.203(10) 0.202(10) -0.017(8) 0.059(8) -0.029(8) F13C 0.220(10) 0.197(10) 0.218(10) 0.039(8) 0.041(8) -0.005(8) C101 0.221(14) 0.208(14) 0.210(14) -0.006(10) 0.065(10) 0.003(10) C102 0.171(12) 0.159(12) 0.161(12) 0.000(9) 0.039(9) 0.011(9) O103 0.152(7) 0.134(7) 0.125(7) 0.001(5) 0.035(6) 0.007(6) C104 0.121(9) 0.113(9) 0.137(10) -0.008(8) 0.019(8) 0.002(8) C105 0.163(11) 0.157(11) 0.140(11) -0.013(9) 0.035(9) 0.013(9) C111 0.201(14) 0.198(14) 0.199(14) 0.009(9) 0.033(9) -0.006(9) C112 0.263(19) 0.263(19) 0.261(19) 0.005(10) 0.064(11) 0.007(10) O113 0.235(10) 0.232(11) 0.231(11) -0.004(7) 0.061(7) 0.015(7) C114 0.270(19) 0.274(19) 0.29(2) -0.003(10) 0.063(11) 0.014(10) C115 0.247(18) 0.263(18) 0.255(18) -0.002(10) 0.063(10) 0.019(10) O201 0.268(12) 0.256(12) 0.265(12) -0.003(7) 0.062(7) 0.007(7) C202 0.49(4) 0.50(4) 0.50(4) -0.008(10) 0.121(14) -0.003(10) O301 0.128(7) 0.114(7) 0.106(7) -0.016(6) 0.017(6) -0.031(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 La O1D 2.550(6) . ? La O1C 2.562(7) . ? La O1A 2.591(6) . ? La O1B 2.591(6) . ? La O11A 2.632(6) . ? La N4D 2.745(8) . ? La N4B 2.755(8) . ? La N4C 2.759(8) . ? La N4A 2.768(8) . ? La N7C 2.771(7) . ? La N7A 2.783(7) . ? O1A C2A 1.233(11) . ? C2A N3A 1.346(12) . ? C2A C21A 1.474(13) . ? C21A C26A 1.381(14) . ? C21A C22A 1.392(14) . ? C22A C23A 1.386(15) . ? C22A H22A 0.9400 . ? C23A C24A 1.379(17) . ? C23A H23A 0.9400 . ? C24A C25A 1.378(16) . ? C24A Br1A 1.897(10) . ? C25A C26A 1.396(14) . ? C25A H25A 0.9400 . ? C26A H26A 0.9400 . ? N3A N4A 1.379(10) . ? N3A H3A 0.8700 . ? N4A C5A 1.271(12) . ? C5A C6A 1.474(13) . ? C5A H5A 0.9400 . ? C6A N7A 1.338(12) . ? C6A C8A 1.374(13) . ? N7A C6B 1.360(12) . ? C8A C9A 1.381(14) . ? C8A H8A 0.9400 . ? C9A C8B 1.395(15) . ? C9A H9A 0.9400 . ? C8B C6B 1.342(13) . ? C8B H8B 0.9400 . ? C6B C5B 1.483(14) . ? C5B N4B 1.278(12) . ? C5B H5B 0.9400 . ? N4B N3B 1.369(11) . ? N3B C2B 1.342(13) . ? N3B H3B 0.8700 . ? C2B O1B 1.250(11) . ? C2B C21B 1.480(14) . ? C21B C26B 1.364(15) . ? C21B C22B 1.377(15) . ? C22B C23B 1.379(16) . ? C22B H22B 0.9400 . ? C23B C24B 1.335(18) . ? C23B H23B 0.9400 . ? C24B C25B 1.379(19) . ? C24B Br1B 1.904(12) . ? C25B C26B 1.398(17) . ? C25B H25B 0.9400 . ? C26B H26B 0.9400 . ? O1C C2C 1.229(11) . ? C2C N3C 1.354(12) . ? C2C C21C 1.465(14) . ? C21C C26C 1.387(13) . ? C21C C22C 1.401(14) . ? C22C C23C 1.400(15) . ? C22C H22C 0.9400 . ? C23C C24C 1.361(15) . ? C23C H23C 0.9400 . ? C24C C25C 1.394(15) . ? C24C Br1C 1.888(10) . ? C25C C26C 1.363(15) . ? C25C H25C 0.9400 . ? C26C H26C 0.9400 . ? N3C N4C 1.392(11) . ? N3C H3C 0.8700 . ? N4C C5C 1.288(11) . ? C5C C6C 1.463(13) . ? C5C H5C 0.9400 . ? C6C N7C 1.355(11) . ? C6C C8C 1.401(13) . ? N7C C6D 1.344(12) . ? C8C C9C 1.351(15) . ? C8C H8C 0.9400 . ? C9C C8D 1.389(15) . ? C9C H9C 0.9400 . ? C8D C6D 1.397(14) . ? C8D H8D 0.9400 . ? C6D C5D 1.452(14) . ? C5D N4D 1.278(12) . ? C5D H5D 0.9400 . ? N4D N3D 1.388(10) . ? N3D C2D 1.355(12) . ? N3D H3D 0.8700 . ? C2D O1D 1.231(11) . ? C2D C21D 1.473(13) . ? C21D C22D 1.377(15) . ? C21D C26D 1.380(14) . ? C22D C23D 1.407(15) . ? C22D H22D 0.9400 . ? C23D C24D 1.390(17) . ? C23D H23D 0.9400 . ? C24D C25D 1.342(16) . ? C24D Br1D 1.900(11) . ? C25D C26D 1.385(14) . ? C25D H25D 0.9400 . ? C26D H26D 0.9400 . ? S1A O13A 1.425(7) . ? S1A O12A 1.432(8) . ? S1A O11A 1.448(7) . ? S1A C11A 1.816(14) . ? C11A F12A 1.290(17) . ? C11A F11A 1.312(17) . ? C11A F13A 1.334(15) . ? S1B O11B 1.429(8) . ? S1B O12B 1.438(7) . ? S1B O13B 1.441(7) . ? S1B C11B 1.800(13) . ? C11B F13B 1.326(15) . ? C11B F12B 1.332(14) . ? C11B F11B 1.341(13) . ? S1C O11C 1.404(15) . ? S1C O12C 1.418(14) . ? S1C O13C 1.427(11) . ? S1C C11C 1.84(3) . ? C11C F13C 1.23(3) . ? C11C F11C 1.31(2) . ? C11C F12C 1.32(2) . ? C101 C102 1.503(9) . ? C101 H10A 0.9700 . ? C101 H10B 0.9700 . ? C101 H10C 0.9700 . ? C102 O103 1.424(9) . ? C102 H10D 0.9800 . ? C102 H10E 0.9800 . ? O103 C104 1.425(8) . ? C104 C105 1.508(9) . ? C104 H10F 0.9800 . ? C104 H10G 0.9800 . ? C105 H10H 0.9700 . ? C105 H10I 0.9700 . ? C105 H10J 0.9700 . ? C111 C112 1.499(9) . ? C111 H11A 0.9700 . ? C111 H11B 0.9700 . ? C111 H11C 0.9700 . ? C112 O113 1.420(9) . ? C112 H11D 0.9800 . ? C112 H11E 0.9800 . ? O113 C114 1.428(9) . ? C114 C115 1.500(9) . ? C114 H11F 0.9800 . ? C114 H11G 0.9800 . ? C115 H11H 0.9700 . ? C115 H11I 0.9700 . ? C115 H11J 0.9700 . ? O201 C202 1.38(6) . ? O201 H201 0.8300 . ? C202 H20A 0.9700 . ? C202 H20B 0.9700 . ? C202 H20C 0.9700 . ? O301 H30A 0.836(11) . ? O301 H30B 0.834(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1D La O1C 122.8(2) . . ? O1D La O1A 88.6(2) . . ? O1C La O1A 89.0(2) . . ? O1D La O1B 90.4(2) . . ? O1C La O1B 136.1(2) . . ? O1A La O1B 122.6(2) . . ? O1D La O11A 134.0(2) . . ? O1C La O11A 67.9(2) . . ? O1A La O11A 137.4(2) . . ? O1B La O11A 68.3(2) . . ? O1D La N4D 58.3(2) . . ? O1C La N4D 155.7(2) . . ? O1A La N4D 66.7(2) . . ? O1B La N4D 64.5(2) . . ? O11A La N4D 131.3(2) . . ? O1D La N4B 71.6(2) . . ? O1C La N4B 102.8(2) . . ? O1A La N4B 160.1(2) . . ? O1B La N4B 58.0(2) . . ? O11A La N4B 62.5(2) . . ? N4D La N4B 100.2(2) . . ? O1D La N4C 163.0(2) . . ? O1C La N4C 57.5(2) . . ? O1A La N4C 74.4(2) . . ? O1B La N4C 99.3(2) . . ? O11A La N4C 63.0(2) . . ? N4D La N4C 113.6(2) . . ? N4B La N4C 125.5(2) . . ? O1D La N4A 69.9(2) . . ? O1C La N4A 61.2(2) . . ? O1A La N4A 57.6(2) . . ? O1B La N4A 160.2(2) . . ? O11A La N4A 126.7(2) . . ? N4D La N4A 102.0(2) . . ? N4B La N4A 114.2(2) . . ? N4C La N4A 99.5(2) . . ? O1D La N7C 116.3(2) . . ? O1C La N7C 114.1(2) . . ? O1A La N7C 65.4(2) . . ? O1B La N7C 64.2(2) . . ? O11A La N7C 91.2(2) . . ? N4D La N7C 58.0(2) . . ? N4B La N7C 121.7(2) . . ? N4C La N7C 57.4(2) . . ? N4A La N7C 122.6(2) . . ? O1D La N7A 64.9(2) . . ? O1C La N7A 64.9(2) . . ? O1A La N7A 115.1(2) . . ? O1B La N7A 115.9(2) . . ? O11A La N7A 87.7(2) . . ? N4D La N7A 123.2(2) . . ? N4B La N7A 58.2(2) . . ? N4C La N7A 121.5(2) . . ? N4A La N7A 57.7(2) . . ? N7C La N7A 178.8(2) . . ? C2A O1A La 128.1(6) . . ? O1A C2A N3A 119.9(9) . . ? O1A C2A C21A 121.8(9) . . ? N3A C2A C21A 118.2(9) . . ? C26A C21A C22A 118.6(9) . . ? C26A C21A C2A 122.5(9) . . ? C22A C21A C2A 118.9(9) . . ? C23A C22A C21A 122.3(11) . . ? C23A C22A H22A 118.8 . . ? C21A C22A H22A 118.8 . . ? C24A C23A C22A 117.5(11) . . ? C24A C23A H23A 121.2 . . ? C22A C23A H23A 121.2 . . ? C25A C24A C23A 121.8(10) . . ? C25A C24A Br1A 118.6(9) . . ? C23A C24A Br1A 119.6(9) . . ? C24A C25A C26A 119.6(10) . . ? C24A C25A H25A 120.2 . . ? C26A C25A H25A 120.2 . . ? C21A C26A C25A 120.0(10) . . ? C21A C26A H26A 120.0 . . ? C25A C26A H26A 120.0 . . ? C2A N3A N4A 116.8(8) . . ? C2A N3A H3A 121.6 . . ? N4A N3A H3A 121.6 . . ? C5A N4A N3A 118.3(8) . . ? C5A N4A La 124.0(6) . . ? N3A N4A La 117.1(5) . . ? N4A C5A C6A 118.4(9) . . ? N4A C5A H5A 120.8 . . ? C6A C5A H5A 120.8 . . ? N7A C6A C8A 122.5(9) . . ? N7A C6A C5A 116.5(8) . . ? C8A C6A C5A 121.0(9) . . ? C6A N7A C6B 116.8(8) . . ? C6A N7A La 121.5(6) . . ? C6B N7A La 120.4(6) . . ? C6A C8A C9A 120.8(10) . . ? C6A C8A H8A 119.6 . . ? C9A C8A H8A 119.6 . . ? C8A C9A C8B 115.8(9) . . ? C8A C9A H9A 122.1 . . ? C8B C9A H9A 122.1 . . ? C6B C8B C9A 121.1(10) . . ? C6B C8B H8B 119.5 . . ? C9A C8B H8B 119.5 . . ? C8B C6B N7A 122.8(9) . . ? C8B C6B C5B 121.6(9) . . ? N7A C6B C5B 115.5(8) . . ? N4B C5B C6B 119.2(9) . . ? N4B C5B H5B 120.4 . . ? C6B C5B H5B 120.4 . . ? C5B N4B N3B 117.6(8) . . ? C5B N4B La 122.7(7) . . ? N3B N4B La 117.3(5) . . ? C2B N3B N4B 117.1(8) . . ? C2B N3B H3B 121.5 . . ? N4B N3B H3B 121.5 . . ? O1B C2B N3B 120.0(9) . . ? O1B C2B C21B 121.4(9) . . ? N3B C2B C21B 118.5(9) . . ? C26B C21B C22B 118.1(10) . . ? C26B C21B C2B 118.0(10) . . ? C22B C21B C2B 123.9(10) . . ? C21B C22B C23B 121.6(12) . . ? C21B C22B H22B 119.2 . . ? C23B C22B H22B 119.2 . . ? C24B C23B C22B 119.2(12) . . ? C24B C23B H23B 120.4 . . ? C22B C23B H23B 120.4 . . ? C23B C24B C25B 121.9(12) . . ? C23B C24B Br1B 119.6(10) . . ? C25B C24B Br1B 118.4(11) . . ? C24B C25B C26B 117.8(13) . . ? C24B C25B H25B 121.1 . . ? C26B C25B H25B 121.1 . . ? C21B C26B C25B 121.2(12) . . ? C21B C26B H26B 119.4 . . ? C25B C26B H26B 119.4 . . ? C2B O1B La 126.6(6) . . ? C2C O1C La 128.6(6) . . ? O1C C2C N3C 119.8(9) . . ? O1C C2C C21C 121.5(9) . . ? N3C C2C C21C 118.7(9) . . ? C26C C21C C22C 117.4(10) . . ? C26C C21C C2C 118.1(9) . . ? C22C C21C C2C 124.0(9) . . ? C23C C22C C21C 121.7(10) . . ? C23C C22C H22C 119.1 . . ? C21C C22C H22C 119.1 . . ? C24C C23C C22C 118.4(10) . . ? C24C C23C H23C 120.8 . . ? C22C C23C H23C 120.8 . . ? C23C C24C C25C 120.9(10) . . ? C23C C24C Br1C 119.7(9) . . ? C25C C24C Br1C 119.4(9) . . ? C26C C25C C24C 120.1(10) . . ? C26C C25C H25C 120.0 . . ? C24C C25C H25C 120.0 . . ? C25C C26C C21C 121.4(10) . . ? C25C C26C H26C 119.3 . . ? C21C C26C H26C 119.3 . . ? C2C N3C N4C 115.2(8) . . ? C2C N3C H3C 122.4 . . ? N4C N3C H3C 122.4 . . ? C5C N4C N3C 117.0(8) . . ? C5C N4C La 122.5(7) . . ? N3C N4C La 117.1(5) . . ? N4C C5C C6C 116.9(9) . . ? N4C C5C H5C 121.6 . . ? C6C C5C H5C 121.6 . . ? N7C C6C C8C 122.4(9) . . ? N7C C6C C5C 116.7(8) . . ? C8C C6C C5C 120.8(9) . . ? C6D N7C C6C 117.9(8) . . ? C6D N7C La 121.0(5) . . ? C6C N7C La 120.5(6) . . ? C9C C8C C6C 118.2(10) . . ? C9C C8C H8C 120.9 . . ? C6C C8C H8C 120.9 . . ? C8C C9C C8D 121.2(11) . . ? C8C C9C H9C 119.4 . . ? C8D C9C H9C 119.4 . . ? C9C C8D C6D 117.4(10) . . ? C9C C8D H8D 121.3 . . ? C6D C8D H8D 121.3 . . ? N7C C6D C8D 122.7(9) . . ? N7C C6D C5D 117.9(8) . . ? C8D C6D C5D 119.3(10) . . ? N4D C5D C6D 117.5(9) . . ? N4D C5D H5D 121.3 . . ? C6D C5D H5D 121.3 . . ? C5D N4D N3D 117.6(8) . . ? C5D N4D La 125.0(6) . . ? N3D N4D La 117.3(5) . . ? C2D N3D N4D 115.4(8) . . ? C2D N3D H3D 122.3 . . ? N4D N3D H3D 122.3 . . ? O1D C2D N3D 120.7(8) . . ? O1D C2D C21D 121.4(9) . . ? N3D C2D C21D 118.0(9) . . ? C22D C21D C26D 118.0(9) . . ? C22D C21D C2D 124.7(9) . . ? C26D C21D C2D 117.3(9) . . ? C21D C22D C23D 122.6(11) . . ? C21D C22D H22D 118.7 . . ? C23D C22D H22D 118.7 . . ? C24D C23D C22D 115.6(11) . . ? C24D C23D H23D 122.2 . . ? C22D C23D H23D 122.2 . . ? C25D C24D C23D 123.5(10) . . ? C25D C24D Br1D 119.0(9) . . ? C23D C24D Br1D 117.5(10) . . ? C24D C25D C26D 119.1(11) . . ? C24D C25D H25D 120.4 . . ? C26D C25D H25D 120.4 . . ? C21D C26D C25D 121.1(10) . . ? C21D C26D H26D 119.4 . . ? C25D C26D H26D 119.4 . . ? C2D O1D La 128.3(6) . . ? O13A S1A O12A 114.5(5) . . ? O13A S1A O11A 115.2(4) . . ? O12A S1A O11A 113.9(4) . . ? O13A S1A C11A 106.2(7) . . ? O12A S1A C11A 103.7(6) . . ? O11A S1A C11A 101.2(6) . . ? S1A O11A La 153.2(4) . . ? F12A C11A F11A 108.9(14) . . ? F12A C11A F13A 105.0(12) . . ? F11A C11A F13A 108.7(14) . . ? F12A C11A S1A 111.5(12) . . ? F11A C11A S1A 111.8(10) . . ? F13A C11A S1A 110.5(11) . . ? O11B S1B O12B 116.4(5) . . ? O11B S1B O13B 113.8(4) . . ? O12B S1B O13B 114.2(4) . . ? O11B S1B C11B 103.4(5) . . ? O12B S1B C11B 103.5(6) . . ? O13B S1B C11B 103.3(5) . . ? F13B C11B F12B 107.1(11) . . ? F13B C11B F11B 107.6(12) . . ? F12B C11B F11B 106.8(10) . . ? F13B C11B S1B 112.8(9) . . ? F12B C11B S1B 111.1(10) . . ? F11B C11B S1B 111.2(9) . . ? O11C S1C O12C 118.4(10) . . ? O11C S1C O13C 115.4(8) . . ? O12C S1C O13C 114.3(9) . . ? O11C S1C C11C 105.3(11) . . ? O12C S1C C11C 98.2(11) . . ? O13C S1C C11C 101.2(10) . . ? F13C C11C F11C 109(2) . . ? F13C C11C F12C 117(3) . . ? F11C C11C F12C 107(2) . . ? F13C C11C S1C 112.4(19) . . ? F11C C11C S1C 107(2) . . ? F12C C11C S1C 104.2(19) . . ? C102 C101 H10A 109.5 . . ? C102 C101 H10B 109.5 . . ? H10A C101 H10B 109.5 . . ? C102 C101 H10C 109.5 . . ? H10A C101 H10C 109.5 . . ? H10B C101 H10C 109.5 . . ? O103 C102 C101 110.6(12) . . ? O103 C102 H10D 109.5 . . ? C101 C102 H10D 109.5 . . ? O103 C102 H10E 109.5 . . ? C101 C102 H10E 109.5 . . ? H10D C102 H10E 108.1 . . ? C102 O103 C104 111.0(10) . . ? O103 C104 C105 110.0(11) . . ? O103 C104 H10F 109.7 . . ? C105 C104 H10F 109.7 . . ? O103 C104 H10G 109.7 . . ? C105 C104 H10G 109.7 . . ? H10F C104 H10G 108.2 . . ? C104 C105 H10H 109.5 . . ? C104 C105 H10I 109.5 . . ? H10H C105 H10I 109.5 . . ? C104 C105 H10J 109.5 . . ? H10H C105 H10J 109.5 . . ? H10I C105 H10J 109.5 . . ? C112 C111 H11A 109.5 . . ? C112 C111 H11B 109.5 . . ? H11A C111 H11B 109.5 . . ? C112 C111 H11C 109.5 . . ? H11A C111 H11C 109.5 . . ? H11B C111 H11C 109.5 . . ? O113 C112 C111 110.7(13) . . ? O113 C112 H11D 109.5 . . ? C111 C112 H11D 109.5 . . ? O113 C112 H11E 109.5 . . ? C111 C112 H11E 109.5 . . ? H11D C112 H11E 108.1 . . ? C112 O113 C114 110.5(13) . . ? O113 C114 C115 112.0(14) . . ? O113 C114 H11F 109.2 . . ? C115 C114 H11F 109.2 . . ? O113 C114 H11G 109.2 . . ? C115 C114 H11G 109.2 . . ? H11F C114 H11G 107.9 . . ? C114 C115 H11H 109.5 . . ? C114 C115 H11I 109.5 . . ? H11H C115 H11I 109.5 . . ? C114 C115 H11J 109.5 . . ? H11H C115 H11J 109.5 . . ? H11I C115 H11J 109.5 . . ? C202 O201 H201 109.5 . . ? O201 C202 H20A 109.5 . . ? O201 C202 H20B 109.5 . . ? H20A C202 H20B 109.5 . . ? O201 C202 H20C 109.5 . . ? H20A C202 H20C 109.5 . . ? H20B C202 H20C 109.5 . . ? H30A O301 H30B 113(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 O1D La O1A C2A 72.8(8) . . . . ? O1C La O1A C2A -50.1(8) . . . . ? O1B La O1A C2A 162.3(8) . . . . ? O11A La O1A C2A -104.9(8) . . . . ? N4D La O1A C2A 128.6(8) . . . . ? N4B La O1A C2A 77.0(11) . . . . ? N4C La O1A C2A -106.5(8) . . . . ? N4A La O1A C2A 5.8(8) . . . . ? N7C La O1A C2A -167.3(9) . . . . ? N7A La O1A C2A 11.4(9) . . . . ? La O1A C2A N3A -5.9(14) . . . . ? La O1A C2A C21A 175.6(6) . . . . ? O1A C2A C21A C26A -161.4(10) . . . . ? N3A C2A C21A C26A 20.1(15) . . . . ? O1A C2A C21A C22A 16.6(15) . . . . ? N3A C2A C21A C22A -162.0(9) . . . . ? C26A C21A C22A C23A -2.6(16) . . . . ? C2A C21A C22A C23A 179.4(10) . . . . ? C21A C22A C23A C24A 0.0(17) . . . . ? C22A C23A C24A C25A 2.5(18) . . . . ? C22A C23A C24A Br1A -179.8(8) . . . . ? C23A C24A C25A C26A -2.4(18) . . . . ? Br1A C24A C25A C26A 179.9(9) . . . . ? C22A C21A C26A C25A 2.8(16) . . . . ? C2A C21A C26A C25A -179.3(10) . . . . ? C24A C25A C26A C21A -0.4(17) . . . . ? O1A C2A N3A N4A -0.1(14) . . . . ? C21A C2A N3A N4A 178.5(8) . . . . ? C2A N3A N4A C5A 176.7(9) . . . . ? C2A N3A N4A La 4.9(10) . . . . ? O1D La N4A C5A 82.2(8) . . . . ? O1C La N4A C5A -67.2(8) . . . . ? O1A La N4A C5A -176.2(9) . . . . ? O1B La N4A C5A 86.6(10) . . . . ? O11A La N4A C5A -48.3(9) . . . . ? N4D La N4A C5A 131.6(8) . . . . ? N4B La N4A C5A 24.5(8) . . . . ? N4C La N4A C5A -111.6(8) . . . . ? N7C La N4A C5A -168.8(7) . . . . ? N7A La N4A C5A 9.8(7) . . . . ? O1D La N4A N3A -106.6(6) . . . . ? O1C La N4A N3A 104.0(6) . . . . ? O1A La N4A N3A -5.0(6) . . . . ? O1B La N4A N3A -102.2(8) . . . . ? O11A La N4A N3A 122.9(6) . . . . ? N4D La N4A N3A -57.2(6) . . . . ? N4B La N4A N3A -164.3(6) . . . . ? N4C La N4A N3A 59.6(6) . . . . ? N7C La N4A N3A 2.4(7) . . . . ? N7A La N4A N3A -179.0(7) . . . . ? N3A N4A C5A C6A -178.2(8) . . . . ? La N4A C5A C6A -7.1(12) . . . . ? N4A C5A C6A N7A -5.1(13) . . . . ? N4A C5A C6A C8A 173.1(9) . . . . ? C8A C6A N7A C6B 4.0(13) . . . . ? C5A C6A N7A C6B -177.9(8) . . . . ? C8A C6A N7A La -163.5(7) . . . . ? C5A C6A N7A La 14.6(11) . . . . ? O1D La N7A C6A -93.5(7) . . . . ? O1C La N7A C6A 58.2(7) . . . . ? O1A La N7A C6A -17.9(7) . . . . ? O1B La N7A C6A -170.8(6) . . . . ? O11A La N7A C6A 124.7(7) . . . . ? N4D La N7A C6A -95.5(7) . . . . ? N4B La N7A C6A -176.5(8) . . . . ? N4C La N7A C6A 68.6(7) . . . . ? N4A La N7A C6A -12.3(6) . . . . ? N7C La N7A C6A 94(11) . . . . ? O1D La N7A C6B 99.5(7) . . . . ? O1C La N7A C6B -108.9(7) . . . . ? O1A La N7A C6B 175.1(6) . . . . ? O1B La N7A C6B 22.2(7) . . . . ? O11A La N7A C6B -42.3(7) . . . . ? N4D La N7A C6B 97.5(7) . . . . ? N4B La N7A C6B 16.4(6) . . . . ? N4C La N7A C6B -98.5(7) . . . . ? N4A La N7A C6B -179.4(8) . . . . ? N7C La N7A C6B -73(11) . . . . ? N7A C6A C8A C9A -0.3(15) . . . . ? C5A C6A C8A C9A -178.4(9) . . . . ? C6A C8A C9A C8B -3.1(15) . . . . ? C8A C9A C8B C6B 2.8(15) . . . . ? C9A C8B C6B N7A 0.9(15) . . . . ? C9A C8B C6B C5B -178.9(9) . . . . ? C6A N7A C6B C8B -4.3(14) . . . . ? La N7A C6B C8B 163.3(7) . . . . ? C6A N7A C6B C5B 175.6(8) . . . . ? La N7A C6B C5B -16.8(10) . . . . ? C8B C6B C5B N4B -178.7(9) . . . . ? N7A C6B C5B N4B 1.4(13) . . . . ? C6B C5B N4B N3B 176.8(8) . . . . ? C6B C5B N4B La 15.2(12) . . . . ? O1D La N4B C5B -87.6(7) . . . . ? O1C La N4B C5B 33.1(7) . . . . ? O1A La N4B C5B -92.0(10) . . . . ? O1B La N4B C5B 169.9(8) . . . . ? O11A La N4B C5B 89.5(7) . . . . ? N4D La N4B C5B -139.1(7) . . . . ? N4C La N4B C5B 92.1(7) . . . . ? N4A La N4B C5B -30.8(8) . . . . ? N7C La N4B C5B 162.4(7) . . . . ? N7A La N4B C5B -16.2(7) . . . . ? O1D La N4B N3B 110.7(6) . . . . ? O1C La N4B N3B -128.6(6) . . . . ? O1A La N4B N3B 106.3(8) . . . . ? O1B La N4B N3B 8.2(6) . . . . ? O11A La N4B N3B -72.2(6) . . . . ? N4D La N4B N3B 59.3(6) . . . . ? N4C La N4B N3B -69.6(7) . . . . ? N4A La N4B N3B 167.5(6) . . . . ? N7C La N4B N3B 0.7(7) . . . . ? N7A La N4B N3B -177.9(7) . . . . ? C5B N4B N3B C2B -170.9(9) . . . . ? La N4B N3B C2B -8.3(10) . . . . ? N4B N3B C2B O1B 0.4(14) . . . . ? N4B N3B C2B C21B 178.8(8) . . . . ? O1B C2B C21B C26B 7.2(16) . . . . ? N3B C2B C21B C26B -171.2(11) . . . . ? O1B C2B C21B C22B -170.8(11) . . . . ? N3B C2B C21B C22B 10.9(16) . . . . ? C26B C21B C22B C23B 1.1(19) . . . . ? C2B C21B C22B C23B 179.0(12) . . . . ? C21B C22B C23B C24B -1(2) . . . . ? C22B C23B C24B C25B 2(2) . . . . ? C22B C23B C24B Br1B -176.8(11) . . . . ? C23B C24B C25B C26B -5(2) . . . . ? Br1B C24B C25B C26B 174.6(11) . . . . ? C22B C21B C26B C25B -3(2) . . . . ? C2B C21B C26B C25B 178.6(12) . . . . ? C24B C25B C26B C21B 5(2) . . . . ? N3B C2B O1B La 9.0(13) . . . . ? C21B C2B O1B La -169.3(7) . . . . ? O1D La O1B C2B -77.0(8) . . . . ? O1C La O1B C2B 65.0(8) . . . . ? O1A La O1B C2B -165.5(7) . . . . ? O11A La O1B C2B 61.2(8) . . . . ? N4D La O1B C2B -131.2(8) . . . . ? N4B La O1B C2B -9.1(7) . . . . ? N4C La O1B C2B 117.1(8) . . . . ? N4A La O1B C2B -81.1(10) . . . . ? N7C La O1B C2B 163.8(8) . . . . ? N7A La O1B C2B -14.9(8) . . . . ? O1D La O1C C2C -172.5(7) . . . . ? O1A La O1C C2C -84.8(8) . . . . ? O1B La O1C C2C 54.6(8) . . . . ? O11A La O1C C2C 58.5(7) . . . . ? N4D La O1C C2C -87.7(9) . . . . ? N4B La O1C C2C 111.4(8) . . . . ? N4C La O1C C2C -12.7(7) . . . . ? N4A La O1C C2C -137.8(8) . . . . ? N7C La O1C C2C -22.5(8) . . . . ? N7A La O1C C2C 156.8(8) . . . . ? La O1C C2C N3C 13.4(12) . . . . ? La O1C C2C C21C -163.9(6) . . . . ? O1C C2C C21C C26C 4.5(14) . . . . ? N3C C2C C21C C26C -172.8(9) . . . . ? O1C C2C C21C C22C 176.8(9) . . . . ? N3C C2C C21C C22C -0.6(14) . . . . ? C26C C21C C22C C23C 0.0(16) . . . . ? C2C C21C C22C C23C -172.3(10) . . . . ? C21C C22C C23C C24C 2.0(18) . . . . ? C22C C23C C24C C25C -3.3(18) . . . . ? C22C C23C C24C Br1C 174.4(9) . . . . ? C23C C24C C25C C26C 2.6(18) . . . . ? Br1C C24C C25C C26C -175.1(9) . . . . ? C24C C25C C26C C21C -0.5(18) . . . . ? C22C C21C C26C C25C -0.8(16) . . . . ? C2C C21C C26C C25C 172.0(10) . . . . ? O1C C2C N3C N4C -1.0(12) . . . . ? C21C C2C N3C N4C 176.4(8) . . . . ? C2C N3C N4C C5C -169.1(8) . . . . ? C2C N3C N4C La -9.4(9) . . . . ? O1D La N4C C5C -94.8(10) . . . . ? O1C La N4C C5C 168.8(8) . . . . ? O1A La N4C C5C -92.2(7) . . . . ? O1B La N4C C5C 29.2(7) . . . . ? O11A La N4C C5C 89.0(7) . . . . ? N4D La N4C C5C -36.9(8) . . . . ? N4B La N4C C5C 86.4(7) . . . . ? N4A La N4C C5C -144.6(7) . . . . ? N7C La N4C C5C -21.8(6) . . . . ? N7A La N4C C5C 157.6(7) . . . . ? O1D La N4C N3C 106.7(9) . . . . ? O1C La N4C N3C 10.2(5) . . . . ? O1A La N4C N3C 109.3(6) . . . . ? O1B La N4C N3C -129.3(6) . . . . ? O11A La N4C N3C -69.6(6) . . . . ? N4D La N4C N3C 164.5(5) . . . . ? N4B La N4C N3C -72.2(6) . . . . ? N4A La N4C N3C 56.9(6) . . . . ? N7C La N4C N3C 179.7(7) . . . . ? N7A La N4C N3C -0.9(7) . . . . ? N3C N4C C5C C6C -177.8(7) . . . . ? La N4C C5C C6C 23.6(11) . . . . ? N4C C5C C6C N7C -4.8(12) . . . . ? N4C C5C C6C C8C 170.7(9) . . . . ? C8C C6C N7C C6D -2.9(13) . . . . ? C5C C6C N7C C6D 172.5(8) . . . . ? C8C C6C N7C La 169.0(7) . . . . ? C5C C6C N7C La -15.6(10) . . . . ? O1D La N7C C6D -8.4(7) . . . . ? O1C La N7C C6D -160.5(6) . . . . ? O1A La N7C C6D -83.6(7) . . . . ? O1B La N7C C6D 68.2(7) . . . . ? O11A La N7C C6D 133.3(7) . . . . ? N4D La N7C C6D -6.7(6) . . . . ? N4B La N7C C6D 75.3(7) . . . . ? N4C La N7C C6D -170.2(8) . . . . ? N4A La N7C C6D -90.4(7) . . . . ? N7A La N7C C6D 164(11) . . . . ? O1D La N7C C6C 179.9(6) . . . . ? O1C La N7C C6C 27.8(7) . . . . ? O1A La N7C C6C 104.8(7) . . . . ? O1B La N7C C6C -103.5(7) . . . . ? O11A La N7C C6C -38.4(6) . . . . ? N4D La N7C C6C -178.3(7) . . . . ? N4B La N7C C6C -96.4(6) . . . . ? N4C La N7C C6C 18.1(6) . . . . ? N4A La N7C C6C 97.9(6) . . . . ? N7A La N7C C6C -8(11) . . . . ? N7C C6C C8C C9C 0.7(15) . . . . ? C5C C6C C8C C9C -174.5(10) . . . . ? C6C C8C C9C C8D 2.7(18) . . . . ? C8C C9C C8D C6D -3.6(18) . . . . ? C6C N7C C6D C8D 1.9(14) . . . . ? La N7C C6D C8D -170.0(8) . . . . ? C6C N7C C6D C5D -178.9(8) . . . . ? La N7C C6D C5D 9.3(12) . . . . ? C9C C8D C6D N7C 1.3(16) . . . . ? C9C C8D C6D C5D -177.9(10) . . . . ? N7C C6D C5D N4D -5.4(14) . . . . ? C8D C6D C5D N4D 173.9(10) . . . . ? C6D C5D N4D N3D -179.2(8) . . . . ? C6D C5D N4D La -1.2(13) . . . . ? O1D La N4D C5D -178.0(9) . . . . ? O1C La N4D C5D 81.6(9) . . . . ? O1A La N4D C5D 78.5(8) . . . . ? O1B La N4D C5D -70.3(8) . . . . ? O11A La N4D C5D -55.0(9) . . . . ? N4B La N4D C5D -117.2(8) . . . . ? N4C La N4D C5D 19.0(9) . . . . ? N4A La N4D C5D 125.1(8) . . . . ? N7C La N4D C5D 3.9(7) . . . . ? N7A La N4D C5D -175.8(7) . . . . ? O1D La N4D N3D 0.1(5) . . . . ? O1C La N4D N3D -100.3(7) . . . . ? O1A La N4D N3D -103.5(6) . . . . ? O1B La N4D N3D 107.7(6) . . . . ? O11A La N4D N3D 123.0(6) . . . . ? N4B La N4D N3D 60.8(6) . . . . ? N4C La N4D N3D -163.0(6) . . . . ? N4A La N4D N3D -56.9(6) . . . . ? N7C La N4D N3D -178.1(7) . . . . ? N7A La N4D N3D 2.2(7) . . . . ? C5D N4D N3D C2D 177.1(9) . . . . ? La N4D N3D C2D -1.0(10) . . . . ? N4D N3D C2D O1D 2.0(13) . . . . ? N4D N3D C2D C21D -177.6(8) . . . . ? O1D C2D C21D C22D -163.0(10) . . . . ? N3D C2D C21D C22D 16.5(15) . . . . ? O1D C2D C21D C26D 14.9(14) . . . . ? N3D C2D C21D C26D -165.5(9) . . . . ? C26D C21D C22D C23D -1.1(17) . . . . ? C2D C21D C22D C23D 176.8(11) . . . . ? C21D C22D C23D C24D -0.3(19) . . . . ? C22D C23D C24D C25D 1(2) . . . . ? C22D C23D C24D Br1D -178.7(9) . . . . ? C23D C24D C25D C26D -0.5(19) . . . . ? Br1D C24D C25D C26D 179.4(8) . . . . ? C22D C21D C26D C25D 1.8(15) . . . . ? C2D C21D C26D C25D -176.3(9) . . . . ? C24D C25D C26D C21D -1.1(16) . . . . ? N3D C2D O1D La -2.3(13) . . . . ? C21D C2D O1D La 177.3(6) . . . . ? O1C La O1D C2D 152.4(7) . . . . ? O1A La O1D C2D 64.4(8) . . . . ? O1B La O1D C2D -58.2(8) . . . . ? O11A La O1D C2D -117.7(7) . . . . ? N4D La O1D C2D 1.2(7) . . . . ? N4B La O1D C2D -114.1(8) . . . . ? N4C La O1D C2D 66.9(12) . . . . ? N4A La O1D C2D 120.3(8) . . . . ? N7C La O1D C2D 2.9(8) . . . . ? N7A La O1D C2D -176.9(8) . . . . ? O13A S1A O11A La 53.2(10) . . . . ? O12A S1A O11A La -82.1(9) . . . . ? C11A S1A O11A La 167.3(10) . . . . ? O1D La O11A S1A -65.6(10) . . . . ? O1C La O11A S1A 49.3(9) . . . . ? O1A La O11A S1A 111.3(9) . . . . ? O1B La O11A S1A -133.6(9) . . . . ? N4D La O11A S1A -148.5(8) . . . . ? N4B La O11A S1A -69.5(9) . . . . ? N4C La O11A S1A 112.9(9) . . . . ? N4A La O11A S1A 31.4(10) . . . . ? N7C La O11A S1A 164.9(9) . . . . ? N7A La O11A S1A -14.4(9) . . . . ? O13A S1A C11A F12A -179.3(10) . . . . ? O12A S1A C11A F12A -58.3(12) . . . . ? O11A S1A C11A F12A 60.0(12) . . . . ? O13A S1A C11A F11A 58.4(13) . . . . ? O12A S1A C11A F11A 179.4(11) . . . . ? O11A S1A C11A F11A -62.3(12) . . . . ? O13A S1A C11A F13A -62.9(13) . . . . ? O12A S1A C11A F13A 58.1(13) . . . . ? O11A S1A C11A F13A 176.4(11) . . . . ? O11B S1B C11B F13B 57.4(10) . . . . ? O12B S1B C11B F13B 179.2(9) . . . . ? O13B S1B C11B F13B -61.5(10) . . . . ? O11B S1B C11B F12B -62.8(10) . . . . ? O12B S1B C11B F12B 58.9(10) . . . . ? O13B S1B C11B F12B 178.3(9) . . . . ? O11B S1B C11B F11B 178.4(9) . . . . ? O12B S1B C11B F11B -59.9(11) . . . . ? O13B S1B C11B F11B 59.5(10) . . . . ? O11C S1C C11C F13C 177(2) . . . . ? O12C S1C C11C F13C -61(2) . . . . ? O13C S1C C11C F13C 56(2) . . . . ? O11C S1C C11C F11C -62.9(19) . . . . ? O12C S1C C11C F11C 59.7(19) . . . . ? O13C S1C C11C F11C 176.6(16) . . . . ? O11C S1C C11C F12C 50(2) . . . . ? O12C S1C C11C F12C 172.3(18) . . . . ? O13C S1C C11C F12C -70.7(19) . . . . ? C101 C102 O103 C104 -171.9(19) . . . . ? C102 O103 C104 C105 178.9(18) . . . . ? C111 C112 O113 C114 -177(3) . . . . ? C112 O113 C114 C115 -157(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.164 _refine_diff_density_min -0.904 _refine_diff_density_rms 0.123 # Attachment 'fro4515.cif' data_fro4515 _database_code_depnum_ccdc_archive 'CCDC 728923' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H27 N10 Nd O13' _chemical_formula_weight 723.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.8305(2) _cell_length_b 13.0671(2) _cell_length_c 11.9848(1) _cell_angle_alpha 90.00 _cell_angle_beta 112.920(1) _cell_angle_gamma 90.00 _cell_volume 2860.40(6) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2984 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.88 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1452 _exptl_absorpt_coefficient_mu 1.892 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4831 _exptl_absorpt_correction_T_max 0.6491 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995 & 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9102 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.87 _reflns_number_total 3368 _reflns_number_gt 3232 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0190P)^2^+1.8282P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at N3 from difmap. others geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0041(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3368 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0195 _refine_ls_R_factor_gt 0.0183 _refine_ls_wR_factor_ref 0.0463 _refine_ls_wR_factor_gt 0.0458 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Nd Nd 0.0000 0.726239(8) 0.2500 0.02221(6) Uani 1 2 d S . . O1 O -0.05705(7) 0.81338(10) 0.04327(11) 0.0355(3) Uani 1 1 d . . . C2 C -0.09507(10) 0.77174(12) -0.05304(18) 0.0301(4) Uani 1 1 d . . . C21 C -0.13152(11) 0.82966(16) -0.16817(18) 0.0427(4) Uani 1 1 d . . . H21A H -0.1745 0.8641 -0.1669 0.064 Uiso 1 1 calc R . . H21B H -0.1460 0.7826 -0.2361 0.064 Uiso 1 1 calc R . . H21C H -0.0978 0.8799 -0.1764 0.064 Uiso 1 1 calc R . . N3 N -0.10631(8) 0.66983(12) -0.05967(14) 0.0321(3) Uani 1 1 d . . . H3 H -0.1281(14) 0.6396(19) -0.123(2) 0.050(7) Uiso 1 1 d . . . N4 N -0.07122(8) 0.61571(10) 0.04553(13) 0.0276(3) Uani 1 1 d . . . C5 C -0.07608(10) 0.51825(13) 0.03862(16) 0.0316(4) Uani 1 1 d . . . H5 H -0.1037 0.4853 -0.0348 0.038 Uiso 1 1 calc R . . C6 C -0.03725(10) 0.45987(12) 0.14898(16) 0.0298(3) Uani 1 1 d . . . N7 N 0.0000 0.51309(14) 0.2500 0.0261(4) Uani 1 2 d S . . C8 C -0.03904(12) 0.35288(13) 0.14559(19) 0.0392(4) Uani 1 1 d . . . H8 H -0.0664 0.3181 0.0734 0.047 Uiso 1 1 calc R . . C9 C 0.0000 0.29934(19) 0.2500 0.0426(7) Uani 1 2 d S . . H9 H 0.0000 0.2274 0.2500 0.051 Uiso 1 2 calc SR . . N11 N 0.0000 0.95283(15) 0.2500 0.0348(5) Uani 1 2 d S . . O12 O 0.05294(7) 0.90312(10) 0.24349(12) 0.0366(3) Uani 1 1 d . . . O13 O 0.0000 1.04707(15) 0.2500 0.0617(7) Uani 1 2 d S . . N15 N -0.14051(8) 0.68916(12) 0.28306(16) 0.0368(3) Uani 1 1 d . . . O16 O -0.14357(9) 0.71779(12) 0.18120(16) 0.0515(4) Uani 1 1 d . . . O17 O -0.07719(7) 0.67441(12) 0.36306(13) 0.0437(3) Uani 1 1 d . . . O18 O -0.19456(9) 0.67635(16) 0.30642(19) 0.0664(5) Uani 1 1 d . . . O31 O -0.18433(9) 0.56623(13) -0.27158(15) 0.0613(4) Uani 1 1 d . . . C32 C -0.25091(13) 0.58082(16) -0.31754(19) 0.0478(5) Uani 1 1 d . . . H32 H -0.2720 0.6160 -0.2708 0.057 Uiso 1 1 calc R . . N33 N -0.29521(10) 0.55118(13) -0.42697(15) 0.0433(4) Uani 1 1 d . . . C34 C -0.26692(16) 0.4929(3) -0.5029(2) 0.0751(8) Uani 1 1 d . . . H34A H -0.2556 0.5391 -0.5565 0.113 Uiso 1 1 calc R . . H34B H -0.3034 0.4438 -0.5505 0.113 Uiso 1 1 calc R . . H34C H -0.2228 0.4570 -0.4520 0.113 Uiso 1 1 calc R . . C35 C -0.37285(13) 0.5774(2) -0.4785(2) 0.0589(6) Uani 1 1 d . . . H35A H -0.3859 0.6105 -0.4172 0.088 Uiso 1 1 calc R . . H35B H -0.4017 0.5156 -0.5061 0.088 Uiso 1 1 calc R . . H35C H -0.3826 0.6236 -0.5463 0.088 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Nd 0.02387(8) 0.01672(8) 0.02407(8) 0.000 0.00720(5) 0.000 O1 0.0435(7) 0.0241(6) 0.0293(6) 0.0007(5) 0.0036(5) -0.0025(5) C2 0.0282(8) 0.0286(9) 0.0291(9) 0.0009(6) 0.0063(7) 0.0019(6) C21 0.0434(10) 0.0378(10) 0.0337(10) 0.0057(8) 0.0007(8) 0.0038(8) N3 0.0318(7) 0.0291(7) 0.0250(7) -0.0022(6) -0.0002(6) -0.0013(6) N4 0.0272(7) 0.0252(7) 0.0265(7) -0.0002(5) 0.0063(5) -0.0005(5) C5 0.0344(9) 0.0254(8) 0.0326(9) -0.0061(7) 0.0105(7) -0.0046(7) C6 0.0363(9) 0.0206(7) 0.0346(9) -0.0030(6) 0.0161(7) -0.0031(6) N7 0.0300(10) 0.0178(9) 0.0312(10) 0.000 0.0128(8) 0.000 C8 0.0579(12) 0.0213(8) 0.0415(10) -0.0067(7) 0.0228(9) -0.0069(8) C9 0.069(2) 0.0155(10) 0.0517(17) 0.000 0.0328(15) 0.000 N11 0.0488(13) 0.0212(9) 0.0243(10) 0.000 0.0032(9) 0.000 O12 0.0412(7) 0.0304(6) 0.0374(7) -0.0013(5) 0.0146(6) -0.0065(5) O13 0.0815(17) 0.0170(9) 0.0650(15) 0.000 0.0051(13) 0.000 N15 0.0306(7) 0.0317(8) 0.0509(10) -0.0006(7) 0.0190(7) -0.0007(6) O16 0.0352(8) 0.0670(11) 0.0443(9) 0.0112(7) 0.0069(7) -0.0023(6) O17 0.0334(7) 0.0577(9) 0.0414(8) 0.0127(7) 0.0162(6) 0.0042(6) O18 0.0395(8) 0.0757(12) 0.0969(14) 0.0055(11) 0.0405(9) -0.0010(8) O31 0.0537(10) 0.0575(10) 0.0474(9) -0.0107(7) -0.0078(7) -0.0065(8) C32 0.0621(14) 0.0338(10) 0.0350(10) -0.0054(8) 0.0052(9) -0.0032(9) N33 0.0421(9) 0.0465(10) 0.0329(8) -0.0039(7) 0.0055(7) -0.0034(7) C34 0.0582(15) 0.113(2) 0.0494(15) -0.0241(15) 0.0158(12) -0.0013(15) C35 0.0490(13) 0.0569(14) 0.0561(14) -0.0024(11) 0.0043(11) 0.0066(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Nd O17 2.5007(13) . ? Nd O17 2.5007(13) 2 ? Nd O12 2.5523(12) . ? Nd O12 2.5523(12) 2 ? Nd O1 2.5558(13) 2 ? Nd O1 2.5558(13) . ? Nd O16 2.6399(16) . ? Nd O16 2.6399(16) 2 ? Nd N4 2.7185(14) . ? Nd N4 2.7185(14) 2 ? Nd N7 2.7852(19) . ? Nd N11 2.961(2) . ? O1 C2 1.232(2) . ? C2 N3 1.347(2) . ? C2 C21 1.491(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 H21C 0.9700 . ? N3 N4 1.375(2) . ? N3 H3 0.81(3) . ? N4 C5 1.277(2) . ? C5 C6 1.460(2) . ? C5 H5 0.9400 . ? C6 N7 1.3411(19) . ? C6 C8 1.399(2) . ? N7 C6 1.3411(19) 2 ? C8 C9 1.378(2) . ? C8 H8 0.9400 . ? C9 C8 1.378(2) 2 ? C9 H9 0.9400 . ? N11 O13 1.231(3) . ? N11 O12 1.2625(17) 2 ? N11 O12 1.2625(17) . ? N15 O18 1.220(2) . ? N15 O16 1.255(2) . ? N15 O17 1.263(2) . ? O31 C32 1.232(3) . ? C32 N33 1.321(2) . ? C32 H32 0.9400 . ? N33 C34 1.456(3) . ? N33 C35 1.459(3) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 H34C 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C35 H35C 0.9700 . ? 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 O17 Nd O17 148.58(7) . 2 ? O17 Nd O12 127.42(5) . . ? O17 Nd O12 83.27(5) 2 . ? O17 Nd O12 83.27(5) . 2 ? O17 Nd O12 127.42(5) 2 2 ? O12 Nd O12 50.20(6) . 2 ? O17 Nd O1 74.26(5) . 2 ? O17 Nd O1 120.84(4) 2 2 ? O12 Nd O1 66.05(4) . 2 ? O12 Nd O1 66.36(4) 2 2 ? O17 Nd O1 120.84(4) . . ? O17 Nd O1 74.26(5) 2 . ? O12 Nd O1 66.36(4) . . ? O12 Nd O1 66.05(4) 2 . ? O1 Nd O1 127.09(6) 2 . ? O17 Nd O16 49.05(5) . . ? O17 Nd O16 129.25(5) 2 . ? O12 Nd O16 115.77(5) . . ? O12 Nd O16 68.96(5) 2 . ? O1 Nd O16 109.75(5) 2 . ? O1 Nd O16 72.51(5) . . ? O17 Nd O16 129.25(5) . 2 ? O17 Nd O16 49.05(5) 2 2 ? O12 Nd O16 68.96(5) . 2 ? O12 Nd O16 115.77(5) 2 2 ? O1 Nd O16 72.51(5) 2 2 ? O1 Nd O16 109.75(5) . 2 ? O16 Nd O16 175.21(7) . 2 ? O17 Nd N4 97.58(5) . . ? O17 Nd N4 65.19(4) 2 . ? O12 Nd N4 121.94(4) . . ? O12 Nd N4 115.67(4) 2 . ? O1 Nd N4 171.50(4) 2 . ? O1 Nd N4 58.96(4) . . ? O16 Nd N4 65.02(5) . . ? O16 Nd N4 112.20(5) 2 . ? O17 Nd N4 65.19(4) . 2 ? O17 Nd N4 97.58(5) 2 2 ? O12 Nd N4 115.67(4) . 2 ? O12 Nd N4 121.94(4) 2 2 ? O1 Nd N4 58.96(4) 2 2 ? O1 Nd N4 171.50(4) . 2 ? O16 Nd N4 112.20(5) . 2 ? O16 Nd N4 65.02(5) 2 2 ? N4 Nd N4 115.82(6) . 2 ? O17 Nd N7 74.29(4) . . ? O17 Nd N7 74.29(4) 2 . ? O12 Nd N7 154.90(3) . . ? O12 Nd N7 154.90(3) 2 . ? O1 Nd N7 116.46(3) 2 . ? O1 Nd N7 116.46(3) . . ? O16 Nd N7 87.60(3) . . ? O16 Nd N7 87.60(3) 2 . ? N4 Nd N7 57.91(3) . . ? N4 Nd N7 57.91(3) 2 . ? O17 Nd N11 105.71(4) . . ? O17 Nd N11 105.71(4) 2 . ? O12 Nd N11 25.10(3) . . ? O12 Nd N11 25.10(3) 2 . ? O1 Nd N11 63.54(3) 2 . ? O1 Nd N11 63.54(3) . . ? O16 Nd N11 92.40(3) . . ? O16 Nd N11 92.40(3) 2 . ? N4 Nd N11 122.09(3) . . ? N4 Nd N11 122.09(3) 2 . ? N7 Nd N11 180.0 . . ? C2 O1 Nd 126.13(11) . . ? O1 C2 N3 121.23(16) . . ? O1 C2 C21 122.81(15) . . ? N3 C2 C21 115.96(16) . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 N3 N4 116.18(14) . . ? C2 N3 H3 123.5(18) . . ? N4 N3 H3 119.9(18) . . ? C5 N4 N3 117.06(15) . . ? C5 N4 Nd 125.99(12) . . ? N3 N4 Nd 116.94(10) . . ? N4 C5 C6 117.54(16) . . ? N4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? N7 C6 C8 122.92(17) . . ? N7 C6 C5 117.24(14) . . ? C8 C6 C5 119.84(16) . . ? C6 N7 C6 117.5(2) . 2 ? C6 N7 Nd 121.24(10) . . ? C6 N7 Nd 121.24(10) 2 . ? C9 C8 C6 118.81(19) . . ? C9 C8 H8 120.6 . . ? C6 C8 H8 120.6 . . ? C8 C9 C8 119.0(2) 2 . ? C8 C9 H9 120.5 2 . ? C8 C9 H9 120.5 . . ? O13 N11 O12 120.97(10) . 2 ? O13 N11 O12 120.97(10) . . ? O12 N11 O12 118.07(19) 2 . ? O13 N11 Nd 180.0 . . ? O12 N11 Nd 59.03(10) 2 . ? O12 N11 Nd 59.03(10) . . ? N11 O12 Nd 95.87(10) . . ? O18 N15 O16 123.35(18) . . ? O18 N15 O17 120.48(18) . . ? O16 N15 O17 116.17(15) . . ? O18 N15 Nd 174.63(15) . . ? O16 N15 Nd 61.29(10) . . ? O17 N15 Nd 54.94(8) . . ? N15 O16 Nd 94.06(11) . . ? N15 O17 Nd 100.64(10) . . ? O31 C32 N33 125.5(2) . . ? O31 C32 H32 117.2 . . ? N33 C32 H32 117.2 . . ? C32 N33 C34 120.3(2) . . ? C32 N33 C35 122.4(2) . . ? C34 N33 C35 117.30(19) . . ? N33 C34 H34A 109.5 . . ? N33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N33 C35 H35A 109.5 . . ? N33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O17 Nd O1 C2 -73.70(16) . . . . ? O17 Nd O1 C2 76.10(16) 2 . . . ? O12 Nd O1 C2 165.55(17) . . . . ? O12 Nd O1 C2 -139.21(17) 2 . . . ? O1 Nd O1 C2 -166.87(17) 2 . . . ? O16 Nd O1 C2 -64.99(16) . . . . ? O16 Nd O1 C2 110.54(16) 2 . . . ? N4 Nd O1 C2 5.92(15) . . . . ? N7 Nd O1 C2 13.13(17) . . . . ? N11 Nd O1 C2 -166.87(17) . . . . ? Nd O1 C2 N3 -4.9(3) . . . . ? Nd O1 C2 C21 174.77(14) . . . . ? O1 C2 N3 N4 -2.0(3) . . . . ? C21 C2 N3 N4 178.32(17) . . . . ? C2 N3 N4 C5 -174.14(16) . . . . ? C2 N3 N4 Nd 6.99(19) . . . . ? O17 Nd N4 C5 -63.40(15) . . . . ? O17 Nd N4 C5 89.08(15) 2 . . . ? O12 Nd N4 C5 152.96(14) . . . . ? O12 Nd N4 C5 -149.55(14) 2 . . . ? O1 Nd N4 C5 175.03(16) . . . . ? O16 Nd N4 C5 -101.10(15) . . . . ? O16 Nd N4 C5 74.64(16) 2 . . . ? N4 Nd N4 C5 2.65(13) 2 . . . ? N7 Nd N4 C5 2.65(13) . . . . ? N11 Nd N4 C5 -177.35(13) . . . . ? O17 Nd N4 N3 115.36(12) . . . . ? O17 Nd N4 N3 -92.16(12) 2 . . . ? O12 Nd N4 N3 -28.29(13) . . . . ? O12 Nd N4 N3 29.21(13) 2 . . . ? O1 Nd N4 N3 -6.21(11) . . . . ? O16 Nd N4 N3 77.66(12) . . . . ? O16 Nd N4 N3 -106.60(12) 2 . . . ? N4 Nd N4 N3 -178.59(13) 2 . . . ? N7 Nd N4 N3 -178.59(13) . . . . ? N11 Nd N4 N3 1.41(13) . . . . ? N3 N4 C5 C6 178.22(15) . . . . ? Nd N4 C5 C6 -3.0(2) . . . . ? N4 C5 C6 N7 0.8(2) . . . . ? N4 C5 C6 C8 -178.16(18) . . . . ? C8 C6 N7 C6 0.51(13) . . . 2 ? C5 C6 N7 C6 -178.42(18) . . . 2 ? C8 C6 N7 Nd -179.49(13) . . . . ? C5 C6 N7 Nd 1.58(18) . . . . ? O17 Nd N7 C6 107.76(9) . . . . ? O17 Nd N7 C6 -72.24(9) 2 . . . ? O12 Nd N7 C6 -99.67(11) . . . . ? O12 Nd N7 C6 80.33(11) 2 . . . ? O1 Nd N7 C6 170.70(9) 2 . . . ? O1 Nd N7 C6 -9.30(9) . . . . ? O16 Nd N7 C6 59.80(9) . . . . ? O16 Nd N7 C6 -120.20(9) 2 . . . ? N4 Nd N7 C6 -2.00(9) . . . . ? N4 Nd N7 C6 178.00(9) 2 . . . ? O17 Nd N7 C6 -72.24(9) . . . 2 ? O17 Nd N7 C6 107.76(9) 2 . . 2 ? O12 Nd N7 C6 80.33(11) . . . 2 ? O12 Nd N7 C6 -99.67(11) 2 . . 2 ? O1 Nd N7 C6 -9.30(9) 2 . . 2 ? O1 Nd N7 C6 170.70(9) . . . 2 ? O16 Nd N7 C6 -120.20(9) . . . 2 ? O16 Nd N7 C6 59.80(9) 2 . . 2 ? N4 Nd N7 C6 178.00(9) . . . 2 ? N4 Nd N7 C6 -2.00(9) 2 . . 2 ? N7 C6 C8 C9 -1.0(3) . . . . ? C5 C6 C8 C9 177.89(15) . . . . ? C6 C8 C9 C8 0.48(12) . . . 2 ? O17 Nd N11 O12 -27.42(8) . . . 2 ? O17 Nd N11 O12 152.58(8) 2 . . 2 ? O12 Nd N11 O12 180.0 . . . 2 ? O1 Nd N11 O12 -90.37(8) 2 . . 2 ? O1 Nd N11 O12 89.63(8) . . . 2 ? O16 Nd N11 O12 20.54(8) . . . 2 ? O16 Nd N11 O12 -159.46(8) 2 . . 2 ? N4 Nd N11 O12 82.34(8) . . . 2 ? N4 Nd N11 O12 -97.66(8) 2 . . 2 ? O17 Nd N11 O12 152.58(8) . . . . ? O17 Nd N11 O12 -27.42(8) 2 . . . ? O12 Nd N11 O12 180.0 2 . . . ? O1 Nd N11 O12 89.63(8) 2 . . . ? O1 Nd N11 O12 -90.37(8) . . . . ? O16 Nd N11 O12 -159.46(8) . . . . ? O16 Nd N11 O12 20.54(8) 2 . . . ? N4 Nd N11 O12 -97.66(8) . . . . ? N4 Nd N11 O12 82.34(8) 2 . . . ? O13 N11 O12 Nd 180.0 . . . . ? O12 N11 O12 Nd 0.0 2 . . . ? O17 Nd O12 N11 -33.94(9) . . . . ? O17 Nd O12 N11 153.48(7) 2 . . . ? O12 Nd O12 N11 0.0 2 . . . ? O1 Nd O12 N11 -78.40(7) 2 . . . ? O1 Nd O12 N11 77.76(7) . . . . ? O16 Nd O12 N11 22.91(9) . . . . ? O16 Nd O12 N11 -157.94(9) 2 . . . ? N4 Nd O12 N11 98.34(7) . . . . ? N4 Nd O12 N11 -111.32(7) 2 . . . ? N7 Nd O12 N11 180.0 . . . . ? O17 Nd N15 O16 -177.09(19) . . . . ? O17 Nd N15 O16 -60.84(14) 2 . . . ? O12 Nd N15 O16 76.92(12) . . . . ? O12 Nd N15 O16 73.80(11) 2 . . . ? O1 Nd N15 O16 138.68(11) 2 . . . ? O1 Nd N15 O16 11.05(12) . . . . ? O16 Nd N15 O16 -169.68(15) 2 . . . ? N4 Nd N15 O16 -46.07(11) . . . . ? N4 Nd N15 O16 -162.42(12) 2 . . . ? N7 Nd N15 O16 -104.76(11) . . . . ? N11 Nd N15 O16 75.24(11) . . . . ? O17 Nd N15 O17 116.25(17) 2 . . . ? O12 Nd N15 O17 -105.99(12) . . . . ? O12 Nd N15 O17 -109.11(12) 2 . . . ? O1 Nd N15 O17 -44.23(12) 2 . . . ? O1 Nd N15 O17 -171.86(12) . . . . ? O16 Nd N15 O17 177.09(19) . . . . ? O16 Nd N15 O17 7.41(18) 2 . . . ? N4 Nd N15 O17 131.02(12) . . . . ? N4 Nd N15 O17 14.67(12) 2 . . . ? N7 Nd N15 O17 72.33(11) . . . . ? N11 Nd N15 O17 -107.67(11) . . . . ? O18 N15 O16 Nd 176.83(18) . . . . ? O17 N15 O16 Nd -2.65(17) . . . . ? O17 Nd O16 N15 1.59(10) . . . . ? O17 Nd O16 N15 140.18(11) 2 . . . ? O12 Nd O16 N15 -116.73(11) . . . . ? O12 Nd O16 N15 -98.05(12) 2 . . . ? O1 Nd O16 N15 -44.53(12) 2 . . . ? O1 Nd O16 N15 -168.49(12) . . . . ? N4 Nd O16 N15 128.23(12) . . . . ? N4 Nd O16 N15 19.03(13) 2 . . . ? N7 Nd O16 N15 72.78(11) . . . . ? N11 Nd O16 N15 -107.22(11) . . . . ? O18 N15 O17 Nd -176.66(17) . . . . ? O16 N15 O17 Nd 2.84(18) . . . . ? O17 Nd O17 N15 -102.36(12) 2 . . . ? O12 Nd O17 N15 91.88(12) . . . . ? O12 Nd O17 N15 66.30(12) 2 . . . ? O1 Nd O17 N15 133.57(12) 2 . . . ? O1 Nd O17 N15 9.42(14) . . . . ? O16 Nd O17 N15 -1.61(10) . . . . ? O16 Nd O17 N15 -175.74(10) 2 . . . ? N4 Nd O17 N15 -48.81(12) . . . . ? N4 Nd O17 N15 -163.81(13) 2 . . . ? N7 Nd O17 N15 -102.36(12) . . . . ? N11 Nd O17 N15 77.64(12) . . . . ? O31 C32 N33 C34 2.3(4) . . . . ? O31 C32 N33 C35 -175.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.424 _refine_diff_density_min -0.622 _refine_diff_density_rms 0.060 # Attachment 'fro4555.cif' data_fro4555 _database_code_depnum_ccdc_archive 'CCDC 728924' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H43 Br2 N12 Nd O15' _chemical_formula_weight 1151.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6899(2) _cell_length_b 13.8131(2) _cell_length_c 16.1157(3) _cell_angle_alpha 71.511(1) _cell_angle_beta 77.927(1) _cell_angle_gamma 73.488(1) _cell_volume 2145.14(6) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3104 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.783 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1150 _exptl_absorpt_coefficient_mu 3.154 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4513 _exptl_absorpt_correction_T_max 0.7433 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20205 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.28 _reflns_number_total 10361 _reflns_number_gt 8947 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. DMF groups refined with geometrical (SADI) and thermal (ISOR) restraints, NO3-groups with thermal (ISOR) ones. DMF O31-C35 and O61-C65 heavily disordered, with some very close contacts. Remaining electron density very close to these two molecules. Refinement with split positions did no improve the model. ; _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^)+(0.0755P)^2^+7.7175P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10361 _refine_ls_number_parameters 568 _refine_ls_number_restraints 232 _refine_ls_R_factor_all 0.0602 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1410 _refine_ls_wR_factor_gt 0.1336 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.074 _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 Nd Nd 1.17793(2) 1.317411(18) 0.267625(16) 0.02387(9) Uani 1 1 d . . . O1A O 1.2574(4) 1.3390(3) 0.3984(3) 0.0386(9) Uani 1 1 d . . . C2A C 1.2244(5) 1.4167(4) 0.4272(3) 0.0312(10) Uani 1 1 d . . . C21A C 1.2903(5) 1.4230(4) 0.4975(3) 0.0318(10) Uani 1 1 d . . . C22A C 1.3751(7) 1.3325(5) 0.5396(4) 0.0459(14) Uani 1 1 d . . . H22A H 1.3863 1.2696 0.5249 0.055 Uiso 1 1 calc R . . C23A C 1.4434(7) 1.3336(5) 0.6030(5) 0.0522(17) Uani 1 1 d . . . H23A H 1.5018 1.2723 0.6308 0.063 Uiso 1 1 calc R . . C24A C 1.4251(5) 1.4256(4) 0.6250(4) 0.0358(11) Uani 1 1 d . . . C25A C 1.3398(6) 1.5160(5) 0.5856(4) 0.0416(13) Uani 1 1 d . . . H25A H 1.3281 1.5782 0.6015 0.050 Uiso 1 1 calc R . . C26A C 1.2711(6) 1.5142(5) 0.5224(4) 0.0414(13) Uani 1 1 d . . . H26A H 1.2111 1.5753 0.4960 0.050 Uiso 1 1 calc R . . Br1A Br 1.52108(7) 1.42829(6) 0.71080(4) 0.05030(17) Uani 1 1 d . . . N3A N 1.1271(4) 1.4997(3) 0.3951(3) 0.0325(9) Uani 1 1 d . . . H3A H 1.1004 1.5543 0.4156 0.039 Uiso 1 1 calc R . . N4A N 1.0739(4) 1.4914(3) 0.3282(3) 0.0286(8) Uani 1 1 d . . . C5A C 0.9782(5) 1.5675(4) 0.2981(3) 0.0306(10) Uani 1 1 d . . . H5A H 0.9456 1.6248 0.3223 0.037 Uiso 1 1 calc R . . C6A C 0.9223(5) 1.5619(4) 0.2256(3) 0.0280(9) Uani 1 1 d . . . N7A N 0.9715(4) 1.4766(3) 0.1951(3) 0.0259(8) Uani 1 1 d . . . C8A C 0.8205(6) 1.6451(4) 0.1900(4) 0.0372(12) Uani 1 1 d . . . H8A H 0.7901 1.7043 0.2120 0.045 Uiso 1 1 calc R . . C9A C 0.7656(6) 1.6385(5) 0.1219(4) 0.0415(13) Uani 1 1 d . . . H9A H 0.6970 1.6931 0.0972 0.050 Uiso 1 1 calc R . . C8B C 0.8128(5) 1.5508(4) 0.0907(3) 0.0362(11) Uani 1 1 d . . . H8B H 0.7762 1.5441 0.0452 0.043 Uiso 1 1 calc R . . C6B C 0.9163(5) 1.4723(4) 0.1286(3) 0.0287(9) Uani 1 1 d . . . C5B C 0.9710(5) 1.3798(4) 0.0955(3) 0.0308(10) Uani 1 1 d . . . H5B H 0.9355 1.3709 0.0505 0.037 Uiso 1 1 calc R . . N4B N 1.0682(4) 1.3117(3) 0.1294(3) 0.0289(8) Uani 1 1 d . . . N3B N 1.1192(4) 1.2259(3) 0.0974(3) 0.0331(9) Uani 1 1 d . . . H3B H 1.0871 1.2177 0.0554 0.040 Uiso 1 1 calc R . . C2B C 1.2228(5) 1.1545(4) 0.1347(3) 0.0304(10) Uani 1 1 d . . . O1B O 1.2629(4) 1.1655(3) 0.1968(3) 0.0358(8) Uani 1 1 d . . . C21B C 1.2842(5) 1.0630(4) 0.0980(3) 0.0307(10) Uani 1 1 d . . . C22B C 1.3750(6) 0.9818(4) 0.1437(4) 0.0380(12) Uani 1 1 d . . . H22B H 1.3980 0.9863 0.1953 0.046 Uiso 1 1 calc R . . C23B C 1.4331(6) 0.8924(4) 0.1135(4) 0.0390(12) Uani 1 1 d . . . H23B H 1.4939 0.8362 0.1450 0.047 Uiso 1 1 calc R . . C24B C 1.3997(5) 0.8884(4) 0.0371(3) 0.0320(10) Uani 1 1 d . . . C25B C 1.3137(6) 0.9702(5) -0.0115(4) 0.0424(13) Uani 1 1 d . . . H25B H 1.2943 0.9666 -0.0646 0.051 Uiso 1 1 calc R . . C26B C 1.2557(6) 1.0587(5) 0.0191(4) 0.0429(14) Uani 1 1 d . . . H26B H 1.1971 1.1156 -0.0137 0.051 Uiso 1 1 calc R . . Br1B Br 1.47383(6) 0.76686(5) -0.00369(4) 0.04526(16) Uani 1 1 d . . . N11 N 0.9232(5) 1.2580(4) 0.3645(4) 0.0435(11) Uani 1 1 d U . . O12 O 0.9773(4) 1.2277(4) 0.2977(3) 0.0478(10) Uani 1 1 d U . . O13 O 0.9729(4) 1.3179(3) 0.3857(3) 0.0447(9) Uani 1 1 d U . . O14 O 0.8246(6) 1.2314(5) 0.4084(5) 0.094(2) Uani 1 1 d U . . N15 N 1.3020(5) 1.4717(4) 0.1157(3) 0.0410(11) Uani 1 1 d U . . O16 O 1.2850(5) 1.3890(3) 0.1077(3) 0.0451(10) Uani 1 1 d U . . O17 O 1.2739(5) 1.4847(3) 0.1921(3) 0.0473(10) Uani 1 1 d U . . O18 O 1.3420(7) 1.5371(4) 0.0522(4) 0.0797(18) Uani 1 1 d U . . N19 N 1.3182(9) 0.1196(6) 0.7030(5) 0.078(2) Uani 1 1 d U . . O20 O 1.3342(7) 0.1196(5) 0.7738(4) 0.0812(18) Uani 1 1 d U . . O21 O 1.1956(10) 0.1857(8) 0.6829(6) 0.125(3) Uani 1 1 d U . . O22 O 1.3822(12) 0.0838(6) 0.6524(7) 0.152(4) Uani 1 1 d U . . O31 O 1.2043(5) 1.1529(3) 0.3838(3) 0.0531(11) Uani 1 1 d DU . . C32 C 1.2823(6) 1.0861(4) 0.4269(4) 0.0497(15) Uani 1 1 d DU . . H32 H 1.3629 1.1049 0.4185 0.060 Uiso 1 1 calc R . . N33 N 1.2841(8) 0.9975(5) 0.4802(6) 0.102(3) Uani 1 1 d DU . . C34 C 1.3830(6) 0.9217(4) 0.5318(4) 0.0484(15) Uani 1 1 d DU . . H34A H 1.4639 0.9052 0.4932 0.073 Uiso 1 1 calc R . . H34B H 1.3522 0.8582 0.5621 0.073 Uiso 1 1 calc R . . H34C H 1.3992 0.9508 0.5749 0.073 Uiso 1 1 calc R . . C35 C 1.1709(18) 1.0228(18) 0.5457(13) 0.216(10) Uani 1 1 d DU . . H35A H 1.1973 1.0493 0.5866 0.324 Uiso 1 1 calc R . . H35B H 1.1396 0.9599 0.5777 0.324 Uiso 1 1 calc R . . H35C H 1.1010 1.0757 0.5158 0.324 Uiso 1 1 calc R . . O41 O 1.4152(4) 1.2587(3) 0.2619(3) 0.0443(10) Uani 1 1 d DU . . C42 C 1.5181(4) 1.1993(4) 0.2431(3) 0.0327(10) Uani 1 1 d DU . . H42 H 1.5145 1.1305 0.2482 0.039 Uiso 1 1 calc R . . N43 N 1.6315(4) 1.2214(3) 0.2171(3) 0.0374(10) Uani 1 1 d DU . . C44 C 1.7527(6) 1.1454(6) 0.1979(5) 0.0588(18) Uani 1 1 d DU . . H44A H 1.7361 1.0756 0.2169 0.088 Uiso 1 1 calc R . . H44B H 1.8203 1.1467 0.2291 0.088 Uiso 1 1 calc R . . H44C H 1.7819 1.1635 0.1349 0.088 Uiso 1 1 calc R . . C45 C 1.6430(9) 1.3291(5) 0.2015(8) 0.081(3) Uani 1 1 d DU . . H45A H 1.5603 1.3704 0.2233 0.122 Uiso 1 1 calc R . . H45B H 1.6640 1.3598 0.1387 0.122 Uiso 1 1 calc R . . H45C H 1.7124 1.3284 0.2322 0.122 Uiso 1 1 calc R . . O51 O 0.9608(5) 0.2083(5) -0.0125(3) 0.0643(14) Uani 1 1 d DU . . C52 C 0.8980(6) 0.2429(5) -0.0745(4) 0.0488(14) Uani 1 1 d DU . . H52 H 0.8377 0.3082 -0.0781 0.059 Uiso 1 1 calc R . . N53 N 0.9055(5) 0.1996(4) -0.1355(3) 0.0457(12) Uani 1 1 d DU . . C54 C 0.8240(9) 0.2501(7) -0.2070(5) 0.076(2) Uani 1 1 d DU . . H54A H 0.7677 0.3158 -0.1984 0.114 Uiso 1 1 calc R . . H54B H 0.7702 0.2042 -0.2070 0.114 Uiso 1 1 calc R . . H54C H 0.8802 0.2637 -0.2630 0.114 Uiso 1 1 calc R . . C55 C 0.9956(8) 0.0976(5) -0.1355(6) 0.072(2) Uani 1 1 d DU . . H55A H 1.0802 0.1081 -0.1680 0.108 Uiso 1 1 calc R . . H55B H 0.9596 0.0605 -0.1632 0.108 Uiso 1 1 calc R . . H55C H 1.0069 0.0566 -0.0752 0.108 Uiso 1 1 calc R . . O61 O 1.0077(7) 0.6921(4) 0.4314(4) 0.0740(17) Uani 1 1 d DU . . C62 C 0.9947(15) 0.7859(6) 0.4119(10) 0.132(5) Uani 1 1 d DU . . H62 H 0.9059 0.8197 0.4065 0.158 Uiso 1 1 calc R . . N63 N 1.0620(11) 0.8547(9) 0.3961(8) 0.123(4) Uani 1 1 d DU . . C64 C 1.2057(12) 0.834(2) 0.3909(19) 0.255(12) Uani 1 1 d DU . . H64A H 1.2474 0.7938 0.3485 0.383 Uiso 1 1 calc R . . H64B H 1.2322 0.7939 0.4484 0.383 Uiso 1 1 calc R . . H64C H 1.2323 0.8998 0.3722 0.383 Uiso 1 1 calc R . . C65 C 1.002(2) 0.9654(10) 0.3922(15) 0.196(8) Uani 1 1 d DU . . H65A H 0.9239 0.9886 0.3623 0.294 Uiso 1 1 calc R . . H65B H 1.0641 1.0076 0.3600 0.294 Uiso 1 1 calc R . . H65C H 0.9766 0.9731 0.4516 0.294 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Nd 0.02576(13) 0.02417(13) 0.02356(13) -0.01003(9) -0.00538(9) -0.00330(9) O1A 0.041(2) 0.039(2) 0.042(2) -0.0235(17) -0.0155(17) 0.0040(16) C2A 0.034(3) 0.032(2) 0.030(2) -0.014(2) -0.007(2) -0.004(2) C21A 0.034(3) 0.033(3) 0.030(2) -0.016(2) -0.006(2) -0.003(2) C22A 0.057(4) 0.036(3) 0.051(3) -0.018(3) -0.028(3) 0.001(3) C23A 0.063(4) 0.042(3) 0.058(4) -0.017(3) -0.037(3) 0.003(3) C24A 0.036(3) 0.045(3) 0.031(3) -0.014(2) -0.010(2) -0.009(2) C25A 0.043(3) 0.042(3) 0.047(3) -0.027(3) -0.019(3) 0.004(2) C26A 0.043(3) 0.040(3) 0.045(3) -0.024(2) -0.019(3) 0.006(2) Br1A 0.0519(4) 0.0623(4) 0.0450(3) -0.0207(3) -0.0237(3) -0.0069(3) N3A 0.038(2) 0.032(2) 0.032(2) -0.0175(17) -0.0098(18) -0.0005(18) N4A 0.029(2) 0.033(2) 0.0271(19) -0.0135(16) -0.0051(16) -0.0053(16) C5A 0.034(3) 0.026(2) 0.033(2) -0.0148(19) -0.006(2) -0.0002(19) C6A 0.029(2) 0.027(2) 0.028(2) -0.0088(18) -0.0045(18) -0.0041(18) N7A 0.0278(19) 0.0235(18) 0.0264(19) -0.0076(15) -0.0056(15) -0.0039(15) C8A 0.039(3) 0.030(3) 0.039(3) -0.012(2) -0.008(2) 0.003(2) C9A 0.037(3) 0.041(3) 0.042(3) -0.011(2) -0.017(2) 0.006(2) C8B 0.036(3) 0.042(3) 0.030(3) -0.011(2) -0.011(2) -0.001(2) C6B 0.027(2) 0.034(2) 0.025(2) -0.0095(19) -0.0053(18) -0.0049(19) C5B 0.032(2) 0.035(3) 0.030(2) -0.012(2) -0.0102(19) -0.007(2) N4B 0.031(2) 0.028(2) 0.030(2) -0.0130(16) -0.0053(16) -0.0057(16) N3B 0.037(2) 0.034(2) 0.035(2) -0.0199(18) -0.0108(18) -0.0026(18) C2B 0.035(3) 0.030(2) 0.032(2) -0.0143(19) -0.005(2) -0.008(2) O1B 0.039(2) 0.0344(19) 0.039(2) -0.0217(16) -0.0147(16) 0.0024(15) C21B 0.033(2) 0.031(2) 0.033(2) -0.016(2) -0.006(2) -0.006(2) C22B 0.044(3) 0.038(3) 0.036(3) -0.017(2) -0.015(2) -0.001(2) C23B 0.042(3) 0.034(3) 0.043(3) -0.018(2) -0.015(2) 0.002(2) C24B 0.032(2) 0.033(3) 0.035(3) -0.018(2) -0.001(2) -0.007(2) C25B 0.049(3) 0.043(3) 0.040(3) -0.025(2) -0.015(3) 0.003(3) C26B 0.052(3) 0.037(3) 0.041(3) -0.020(2) -0.020(3) 0.009(2) Br1B 0.0504(3) 0.0385(3) 0.0543(4) -0.0294(3) -0.0172(3) 0.0043(2) N11 0.035(2) 0.033(2) 0.056(3) -0.007(2) 0.005(2) -0.0114(19) O12 0.050(2) 0.059(3) 0.041(2) -0.0119(19) -0.0072(18) -0.023(2) O13 0.046(2) 0.041(2) 0.046(2) -0.0153(18) 0.0039(18) -0.0117(18) O14 0.072(4) 0.077(4) 0.132(5) -0.037(4) 0.047(4) -0.049(3) N15 0.042(3) 0.037(2) 0.040(2) -0.010(2) 0.001(2) -0.009(2) O16 0.058(3) 0.049(2) 0.035(2) -0.0125(17) -0.0050(18) -0.024(2) O17 0.055(3) 0.041(2) 0.049(2) -0.0212(18) 0.0066(19) -0.0166(19) O18 0.110(4) 0.060(3) 0.061(3) -0.011(3) 0.028(3) -0.043(3) N19 0.112(6) 0.079(4) 0.055(4) -0.029(3) 0.010(4) -0.047(4) O20 0.094(4) 0.084(4) 0.068(3) -0.028(3) -0.033(3) 0.002(3) O21 0.116(6) 0.141(6) 0.120(6) -0.028(5) -0.037(5) -0.028(5) O22 0.234(8) 0.074(4) 0.125(6) -0.052(4) 0.058(6) -0.030(5) O31 0.062(3) 0.040(2) 0.053(3) 0.0074(19) -0.028(2) -0.013(2) C32 0.037(3) 0.036(3) 0.065(4) 0.005(3) -0.008(3) -0.012(2) N33 0.092(5) 0.068(4) 0.134(6) 0.048(4) -0.074(5) -0.045(4) C34 0.050(3) 0.036(3) 0.052(3) 0.003(2) -0.014(3) -0.012(3) C35 0.219(13) 0.211(13) 0.220(13) -0.045(9) -0.045(9) -0.054(9) O41 0.0303(19) 0.057(2) 0.052(2) -0.029(2) -0.0079(17) -0.0026(17) C42 0.034(3) 0.037(3) 0.030(2) -0.011(2) -0.0069(19) -0.009(2) N43 0.033(2) 0.041(2) 0.041(2) -0.016(2) -0.0030(18) -0.0082(19) C44 0.037(3) 0.074(4) 0.061(4) -0.029(3) 0.001(3) 0.000(3) C45 0.066(5) 0.067(5) 0.122(7) -0.029(5) -0.006(5) -0.033(4) O51 0.057(3) 0.091(4) 0.061(3) -0.037(3) -0.019(2) -0.015(3) C52 0.044(3) 0.051(3) 0.057(4) -0.019(3) -0.013(3) -0.012(3) N53 0.044(3) 0.057(3) 0.042(3) -0.011(2) -0.011(2) -0.020(2) C54 0.082(5) 0.093(5) 0.062(4) 0.002(4) -0.033(4) -0.045(4) C55 0.075(5) 0.079(5) 0.075(5) -0.043(4) -0.006(4) -0.015(4) O61 0.123(5) 0.038(2) 0.073(3) -0.022(2) -0.053(3) 0.000(3) C62 0.147(9) 0.122(8) 0.150(9) -0.060(7) -0.031(7) -0.034(7) N63 0.126(7) 0.112(6) 0.144(8) -0.048(6) -0.025(6) -0.029(6) C64 0.223(15) 0.267(15) 0.251(15) -0.056(10) -0.029(10) -0.038(10) C65 0.206(12) 0.164(11) 0.209(12) -0.060(9) -0.015(9) -0.028(9) _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 Nd O41 2.425(4) . ? Nd O31 2.431(4) . ? Nd O1B 2.556(3) . ? Nd O1A 2.558(4) . ? Nd O13 2.585(4) . ? Nd O16 2.593(4) . ? Nd O17 2.629(4) . ? Nd O12 2.658(4) . ? Nd N4A 2.735(4) . ? Nd N4B 2.757(4) . ? Nd N7A 2.786(4) . ? O1A C2A 1.235(6) . ? C2A N3A 1.354(7) . ? C2A C21A 1.489(7) . ? C21A C22A 1.386(8) . ? C21A C26A 1.390(7) . ? C22A C23A 1.380(8) . ? C22A H22A 0.9400 . ? C23A C24A 1.376(8) . ? C23A H23A 0.9400 . ? C24A C25A 1.373(8) . ? C24A Br1A 1.901(5) . ? C25A C26A 1.385(7) . ? C25A H25A 0.9400 . ? C26A H26A 0.9400 . ? N3A N4A 1.369(6) . ? N3A H3A 0.8700 . ? N4A C5A 1.288(6) . ? C5A C6A 1.449(7) . ? C5A H5A 0.9400 . ? C6A N7A 1.347(6) . ? C6A C8A 1.402(7) . ? N7A C6B 1.352(6) . ? C8A C9A 1.387(8) . ? C8A H8A 0.9400 . ? C9A C8B 1.380(8) . ? C9A H9A 0.9400 . ? C8B C6B 1.398(7) . ? C8B H8B 0.9400 . ? C6B C5B 1.461(7) . ? C5B N4B 1.273(6) . ? C5B H5B 0.9400 . ? N4B N3B 1.367(6) . ? N3B C2B 1.357(7) . ? N3B H3B 0.8700 . ? C2B O1B 1.234(6) . ? C2B C21B 1.489(6) . ? C21B C22B 1.378(7) . ? C21B C26B 1.390(7) . ? C22B C23B 1.402(7) . ? C22B H22B 0.9400 . ? C23B C24B 1.372(7) . ? C23B H23B 0.9400 . ? C24B C25B 1.373(8) . ? C24B Br1B 1.899(5) . ? C25B C26B 1.396(7) . ? C25B H25B 0.9400 . ? C26B H26B 0.9400 . ? N11 O14 1.221(7) . ? N11 O12 1.248(7) . ? N11 O13 1.260(7) . ? N15 O18 1.222(7) . ? N15 O16 1.256(6) . ? N15 O17 1.263(6) . ? N19 O22 1.098(10) . ? N19 O20 1.188(9) . ? N19 O21 1.403(12) . ? O31 C32 1.194(5) . ? C32 N33 1.249(5) . ? C32 H32 0.9400 . ? N33 C34 1.447(5) . ? N33 C35 1.469(5) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 H34C 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C35 H35C 0.9700 . ? O41 C42 1.216(5) . ? C42 N43 1.286(5) . ? C42 H42 0.9400 . ? N43 C45 1.464(5) . ? N43 C44 1.464(5) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C44 H44C 0.9700 . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C45 H45C 0.9700 . ? O51 C52 1.213(5) . ? C52 N53 1.284(5) . ? C52 H52 0.9400 . ? N53 C54 1.462(5) . ? N53 C55 1.463(5) . ? C54 H54A 0.9700 . ? C54 H54B 0.9700 . ? C54 H54C 0.9700 . ? C55 H55A 0.9700 . ? C55 H55B 0.9700 . ? C55 H55C 0.9700 . ? O61 C62 1.206(6) . ? C62 N63 1.283(6) . ? C62 H62 0.9400 . ? N63 C65 1.468(5) . ? N63 C64 1.469(5) . ? C64 H64A 0.9700 . ? C64 H64B 0.9700 . ? C64 H64C 0.9700 . ? C65 H65A 0.9700 . ? C65 H65B 0.9700 . ? C65 H65C 0.9700 . ? 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 O41 Nd O31 77.69(16) . . ? O41 Nd O1B 69.99(12) . . ? O31 Nd O1B 71.23(15) . . ? O41 Nd O1A 68.35(13) . . ? O31 Nd O1A 70.26(14) . . ? O1B Nd O1A 127.73(11) . . ? O41 Nd O13 138.14(15) . . ? O31 Nd O13 69.18(15) . . ? O1B Nd O13 119.46(13) . . ? O1A Nd O13 76.69(14) . . ? O41 Nd O16 71.15(15) . . ? O31 Nd O16 137.80(16) . . ? O1B Nd O16 71.78(13) . . ? O1A Nd O16 120.51(14) . . ? O13 Nd O16 149.79(14) . . ? O41 Nd O17 73.15(15) . . ? O31 Nd O17 143.50(15) . . ? O1B Nd O17 116.97(13) . . ? O1A Nd O17 78.81(14) . . ? O13 Nd O17 122.28(13) . . ? O16 Nd O17 48.49(13) . . ? O41 Nd O12 136.39(15) . . ? O31 Nd O12 67.16(14) . . ? O1B Nd O12 74.71(14) . . ? O1A Nd O12 118.97(14) . . ? O13 Nd O12 48.42(14) . . ? O16 Nd O12 120.47(13) . . ? O17 Nd O12 148.21(15) . . ? O41 Nd N4A 113.60(13) . . ? O31 Nd N4A 113.88(15) . . ? O1B Nd N4A 173.99(12) . . ? O1A Nd N4A 58.12(12) . . ? O13 Nd N4A 61.50(13) . . ? O16 Nd N4A 104.44(13) . . ? O17 Nd N4A 61.10(13) . . ? O12 Nd N4A 104.00(14) . . ? O41 Nd N4B 117.38(13) . . ? O31 Nd N4B 112.86(14) . . ? O1B Nd N4B 58.42(12) . . ? O1A Nd N4B 173.66(12) . . ? O13 Nd N4B 99.03(13) . . ? O16 Nd N4B 61.31(13) . . ? O17 Nd N4B 99.94(13) . . ? O12 Nd N4B 59.31(13) . . ? N4A Nd N4B 115.78(12) . . ? O41 Nd N7A 144.80(14) . . ? O31 Nd N7A 137.50(14) . . ? O1B Nd N7A 115.93(11) . . ? O1A Nd N7A 116.33(11) . . ? O13 Nd N7A 71.93(13) . . ? O16 Nd N7A 77.99(13) . . ? O17 Nd N7A 73.86(13) . . ? O12 Nd N7A 74.53(13) . . ? N4A Nd N7A 58.27(12) . . ? N4B Nd N7A 57.52(11) . . ? C2A O1A Nd 127.3(3) . . ? O1A C2A N3A 120.8(5) . . ? O1A C2A C21A 121.5(5) . . ? N3A C2A C21A 117.8(4) . . ? C22A C21A C26A 118.9(5) . . ? C22A C21A C2A 117.6(5) . . ? C26A C21A C2A 123.5(5) . . ? C23A C22A C21A 120.7(5) . . ? C23A C22A H22A 119.6 . . ? C21A C22A H22A 119.6 . . ? C24A C23A C22A 119.2(5) . . ? C24A C23A H23A 120.4 . . ? C22A C23A H23A 120.4 . . ? C25A C24A C23A 121.4(5) . . ? C25A C24A Br1A 119.1(4) . . ? C23A C24A Br1A 119.4(4) . . ? C24A C25A C26A 119.1(5) . . ? C24A C25A H25A 120.5 . . ? C26A C25A H25A 120.5 . . ? C25A C26A C21A 120.6(5) . . ? C25A C26A H26A 119.7 . . ? C21A C26A H26A 119.7 . . ? C2A N3A N4A 115.2(4) . . ? C2A N3A H3A 122.4 . . ? N4A N3A H3A 122.4 . . ? C5A N4A N3A 116.8(4) . . ? C5A N4A Nd 125.0(3) . . ? N3A N4A Nd 118.2(3) . . ? N4A C5A C6A 117.9(4) . . ? N4A C5A H5A 121.0 . . ? C6A C5A H5A 121.0 . . ? N7A C6A C8A 122.9(5) . . ? N7A C6A C5A 118.1(4) . . ? C8A C6A C5A 119.0(4) . . ? C6A N7A C6B 117.1(4) . . ? C6A N7A Nd 120.7(3) . . ? C6B N7A Nd 122.2(3) . . ? C9A C8A C6A 118.8(5) . . ? C9A C8A H8A 120.6 . . ? C6A C8A H8A 120.6 . . ? C8B C9A C8A 119.3(5) . . ? C8B C9A H9A 120.3 . . ? C8A C9A H9A 120.3 . . ? C9A C8B C6B 118.3(5) . . ? C9A C8B H8B 120.8 . . ? C6B C8B H8B 120.8 . . ? N7A C6B C8B 123.6(5) . . ? N7A C6B C5B 116.7(4) . . ? C8B C6B C5B 119.7(4) . . ? N4B C5B C6B 118.0(4) . . ? N4B C5B H5B 121.0 . . ? C6B C5B H5B 121.0 . . ? C5B N4B N3B 117.4(4) . . ? C5B N4B Nd 125.5(3) . . ? N3B N4B Nd 117.0(3) . . ? C2B N3B N4B 116.3(4) . . ? C2B N3B H3B 121.9 . . ? N4B N3B H3B 121.9 . . ? O1B C2B N3B 120.7(4) . . ? O1B C2B C21B 122.0(5) . . ? N3B C2B C21B 117.3(4) . . ? C2B O1B Nd 127.6(3) . . ? C22B C21B C26B 119.8(5) . . ? C22B C21B C2B 117.9(4) . . ? C26B C21B C2B 122.3(5) . . ? C21B C22B C23B 120.3(5) . . ? C21B C22B H22B 119.9 . . ? C23B C22B H22B 119.9 . . ? C24B C23B C22B 118.8(5) . . ? C24B C23B H23B 120.6 . . ? C22B C23B H23B 120.6 . . ? C23B C24B C25B 122.0(5) . . ? C23B C24B Br1B 119.6(4) . . ? C25B C24B Br1B 118.4(4) . . ? C24B C25B C26B 118.9(5) . . ? C24B C25B H25B 120.5 . . ? C26B C25B H25B 120.5 . . ? C21B C26B C25B 120.2(5) . . ? C21B C26B H26B 119.9 . . ? C25B C26B H26B 119.9 . . ? O14 N11 O12 121.5(6) . . ? O14 N11 O13 120.4(6) . . ? O12 N11 O13 118.1(5) . . ? N11 O12 Nd 95.0(3) . . ? N11 O13 Nd 98.3(3) . . ? O18 N15 O16 121.5(5) . . ? O18 N15 O17 121.8(5) . . ? O16 N15 O17 116.7(5) . . ? N15 O16 Nd 98.3(3) . . ? N15 O17 Nd 96.3(3) . . ? O22 N19 O20 132.5(12) . . ? O22 N19 O21 118.3(11) . . ? O20 N19 O21 109.0(8) . . ? C32 O31 Nd 143.7(4) . . ? O31 C32 N33 136.3(6) . . ? O31 C32 H32 111.9 . . ? N33 C32 H32 111.9 . . ? C32 N33 C34 132.8(6) . . ? C32 N33 C35 101.1(12) . . ? C34 N33 C35 104.7(12) . . ? N33 C34 H34A 109.5 . . ? N33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N33 C35 H35A 109.5 . . ? N33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C42 O41 Nd 150.2(4) . . ? O41 C42 N43 126.5(5) . . ? O41 C42 H42 116.8 . . ? N43 C42 H42 116.8 . . ? C42 N43 C45 119.8(5) . . ? C42 N43 C44 123.8(5) . . ? C45 N43 C44 116.4(6) . . ? N43 C44 H44A 109.5 . . ? N43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? N43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? N43 C45 H45A 109.5 . . ? N43 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? N43 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? O51 C52 N53 126.6(6) . . ? O51 C52 H52 116.7 . . ? N53 C52 H52 116.7 . . ? C52 N53 C54 121.2(6) . . ? C52 N53 C55 120.9(5) . . ? C54 N53 C55 117.9(6) . . ? N53 C54 H54A 109.5 . . ? N53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? N53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? N53 C55 H55A 109.5 . . ? N53 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? N53 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? O61 C62 N63 140.8(14) . . ? O61 C62 H62 109.6 . . ? N63 C62 H62 109.6 . . ? C62 N63 C65 123.0(13) . . ? C62 N63 C64 126.2(16) . . ? C65 N63 C64 110.4(15) . . ? N63 C64 H64A 109.5 . . ? N63 C64 H64B 109.5 . . ? H64A C64 H64B 109.5 . . ? N63 C64 H64C 109.5 . . ? H64A C64 H64C 109.5 . . ? H64B C64 H64C 109.5 . . ? N63 C65 H65A 109.5 . . ? N63 C65 H65B 109.5 . . ? H65A C65 H65B 109.5 . . ? N63 C65 H65C 109.5 . . ? H65A C65 H65C 109.5 . . ? H65B C65 H65C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O41 Nd O1A C2A 133.4(5) . . . . ? O31 Nd O1A C2A -142.4(5) . . . . ? O1B Nd O1A C2A 172.8(4) . . . . ? O13 Nd O1A C2A -70.1(5) . . . . ? O16 Nd O1A C2A 83.0(5) . . . . ? O17 Nd O1A C2A 57.2(5) . . . . ? O12 Nd O1A C2A -94.5(5) . . . . ? N4A Nd O1A C2A -5.6(4) . . . . ? N7A Nd O1A C2A -8.3(5) . . . . ? Nd O1A C2A N3A 6.8(8) . . . . ? Nd O1A C2A C21A -172.8(4) . . . . ? O1A C2A C21A C22A -10.1(8) . . . . ? N3A C2A C21A C22A 170.3(5) . . . . ? O1A C2A C21A C26A 169.8(6) . . . . ? N3A C2A C21A C26A -9.9(8) . . . . ? C26A C21A C22A C23A -2.4(10) . . . . ? C2A C21A C22A C23A 177.4(6) . . . . ? C21A C22A C23A C24A 0.9(11) . . . . ? C22A C23A C24A C25A 0.4(11) . . . . ? C22A C23A C24A Br1A -179.0(6) . . . . ? C23A C24A C25A C26A -0.1(10) . . . . ? Br1A C24A C25A C26A 179.2(5) . . . . ? C24A C25A C26A C21A -1.4(10) . . . . ? C22A C21A C26A C25A 2.7(9) . . . . ? C2A C21A C26A C25A -177.2(6) . . . . ? O1A C2A N3A N4A -2.2(8) . . . . ? C21A C2A N3A N4A 177.4(4) . . . . ? C2A N3A N4A C5A 177.8(5) . . . . ? C2A N3A N4A Nd -2.6(6) . . . . ? O41 Nd N4A C5A 141.5(4) . . . . ? O31 Nd N4A C5A -132.0(4) . . . . ? O1A Nd N4A C5A -176.7(5) . . . . ? O13 Nd N4A C5A -85.1(4) . . . . ? O16 Nd N4A C5A 66.1(4) . . . . ? O17 Nd N4A C5A 88.6(4) . . . . ? O12 Nd N4A C5A -61.1(4) . . . . ? N4B Nd N4A C5A 1.3(5) . . . . ? N7A Nd N4A C5A 0.4(4) . . . . ? O41 Nd N4A N3A -38.0(4) . . . . ? O31 Nd N4A N3A 48.5(4) . . . . ? O1A Nd N4A N3A 3.8(3) . . . . ? O13 Nd N4A N3A 95.4(4) . . . . ? O16 Nd N4A N3A -113.4(3) . . . . ? O17 Nd N4A N3A -90.9(4) . . . . ? O12 Nd N4A N3A 119.4(3) . . . . ? N4B Nd N4A N3A -178.2(3) . . . . ? N7A Nd N4A N3A -179.1(4) . . . . ? N3A N4A C5A C6A 178.4(4) . . . . ? Nd N4A C5A C6A -1.1(7) . . . . ? N4A C5A C6A N7A 1.4(7) . . . . ? N4A C5A C6A C8A -178.2(5) . . . . ? C8A C6A N7A C6B -1.6(7) . . . . ? C5A C6A N7A C6B 178.8(5) . . . . ? C8A C6A N7A Nd 178.5(4) . . . . ? C5A C6A N7A Nd -1.1(6) . . . . ? O41 Nd N7A C6A -86.2(4) . . . . ? O31 Nd N7A C6A 92.1(4) . . . . ? O1B Nd N7A C6A -177.8(3) . . . . ? O1A Nd N7A C6A 3.1(4) . . . . ? O13 Nd N7A C6A 67.5(4) . . . . ? O16 Nd N7A C6A -115.2(4) . . . . ? O17 Nd N7A C6A -65.2(4) . . . . ? O12 Nd N7A C6A 118.2(4) . . . . ? N4A Nd N7A C6A 0.4(3) . . . . ? N4B Nd N7A C6A -178.7(4) . . . . ? O41 Nd N7A C6B 93.9(4) . . . . ? O31 Nd N7A C6B -87.8(4) . . . . ? O1B Nd N7A C6B 2.3(4) . . . . ? O1A Nd N7A C6B -176.8(4) . . . . ? O13 Nd N7A C6B -112.4(4) . . . . ? O16 Nd N7A C6B 64.9(4) . . . . ? O17 Nd N7A C6B 114.9(4) . . . . ? O12 Nd N7A C6B -61.7(4) . . . . ? N4A Nd N7A C6B -179.5(4) . . . . ? N4B Nd N7A C6B 1.4(3) . . . . ? N7A C6A C8A C9A 1.7(8) . . . . ? C5A C6A C8A C9A -178.7(5) . . . . ? C6A C8A C9A C8B -0.3(9) . . . . ? C8A C9A C8B C6B -1.0(9) . . . . ? C6A N7A C6B C8B 0.2(7) . . . . ? Nd N7A C6B C8B -179.9(4) . . . . ? C6A N7A C6B C5B 179.6(4) . . . . ? Nd N7A C6B C5B -0.5(6) . . . . ? C9A C8B C6B N7A 1.1(8) . . . . ? C9A C8B C6B C5B -178.3(5) . . . . ? N7A C6B C5B N4B -1.9(7) . . . . ? C8B C6B C5B N4B 177.6(5) . . . . ? C6B C5B N4B N3B -179.5(4) . . . . ? C6B C5B N4B Nd 3.6(7) . . . . ? O41 Nd N4B C5B -142.2(4) . . . . ? O31 Nd N4B C5B 130.2(4) . . . . ? O1B Nd N4B C5B 178.2(5) . . . . ? O13 Nd N4B C5B 59.1(4) . . . . ? O16 Nd N4B C5B -96.5(4) . . . . ? O17 Nd N4B C5B -66.2(4) . . . . ? O12 Nd N4B C5B 87.9(4) . . . . ? N4A Nd N4B C5B -3.6(5) . . . . ? N7A Nd N4B C5B -2.7(4) . . . . ? O41 Nd N4B N3B 40.8(4) . . . . ? O31 Nd N4B N3B -46.8(4) . . . . ? O1B Nd N4B N3B 1.2(3) . . . . ? O13 Nd N4B N3B -117.9(3) . . . . ? O16 Nd N4B N3B 86.5(4) . . . . ? O17 Nd N4B N3B 116.9(3) . . . . ? O12 Nd N4B N3B -89.1(4) . . . . ? N4A Nd N4B N3B 179.5(3) . . . . ? N7A Nd N4B N3B -179.6(4) . . . . ? C5B N4B N3B C2B -180.0(5) . . . . ? Nd N4B N3B C2B -2.8(6) . . . . ? N4B N3B C2B O1B 3.3(8) . . . . ? N4B N3B C2B C21B -177.1(4) . . . . ? N3B C2B O1B Nd -2.3(7) . . . . ? C21B C2B O1B Nd 178.2(3) . . . . ? O41 Nd O1B C2B -142.4(5) . . . . ? O31 Nd O1B C2B 134.2(5) . . . . ? O1A Nd O1B C2B 178.7(4) . . . . ? O13 Nd O1B C2B 82.8(5) . . . . ? O16 Nd O1B C2B -66.4(5) . . . . ? O17 Nd O1B C2B -84.5(5) . . . . ? O12 Nd O1B C2B 63.6(4) . . . . ? N4B Nd O1B C2B 0.6(4) . . . . ? N7A Nd O1B C2B -0.2(5) . . . . ? O1B C2B C21B C22B 9.6(8) . . . . ? N3B C2B C21B C22B -169.9(5) . . . . ? O1B C2B C21B C26B -168.6(6) . . . . ? N3B C2B C21B C26B 11.9(8) . . . . ? C26B C21B C22B C23B -3.5(9) . . . . ? C2B C21B C22B C23B 178.2(5) . . . . ? C21B C22B C23B C24B 1.2(9) . . . . ? C22B C23B C24B C25B 1.6(9) . . . . ? C22B C23B C24B Br1B -178.5(4) . . . . ? C23B C24B C25B C26B -1.9(10) . . . . ? Br1B C24B C25B C26B 178.2(5) . . . . ? C22B C21B C26B C25B 3.2(10) . . . . ? C2B C21B C26B C25B -178.6(6) . . . . ? C24B C25B C26B C21B -0.5(10) . . . . ? O14 N11 O12 Nd -176.0(6) . . . . ? O13 N11 O12 Nd 4.4(5) . . . . ? O41 Nd O12 N11 118.3(3) . . . . ? O31 Nd O12 N11 79.3(3) . . . . ? O1B Nd O12 N11 155.0(4) . . . . ? O1A Nd O12 N11 30.0(4) . . . . ? O13 Nd O12 N11 -2.5(3) . . . . ? O16 Nd O12 N11 -147.4(3) . . . . ? O17 Nd O12 N11 -88.1(4) . . . . ? N4A Nd O12 N11 -31.0(4) . . . . ? N4B Nd O12 N11 -142.9(4) . . . . ? N7A Nd O12 N11 -81.9(3) . . . . ? O14 N11 O13 Nd 175.8(6) . . . . ? O12 N11 O13 Nd -4.5(5) . . . . ? O41 Nd O13 N11 -114.9(3) . . . . ? O31 Nd O13 N11 -74.9(3) . . . . ? O1B Nd O13 N11 -22.5(4) . . . . ? O1A Nd O13 N11 -148.6(3) . . . . ? O16 Nd O13 N11 82.3(4) . . . . ? O17 Nd O13 N11 144.1(3) . . . . ? O12 Nd O13 N11 2.5(3) . . . . ? N4A Nd O13 N11 150.7(4) . . . . ? N4B Nd O13 N11 36.2(3) . . . . ? N7A Nd O13 N11 87.6(3) . . . . ? O18 N15 O16 Nd -173.8(6) . . . . ? O17 N15 O16 Nd 5.0(5) . . . . ? O41 Nd O16 N15 -86.7(3) . . . . ? O31 Nd O16 N15 -131.3(3) . . . . ? O1B Nd O16 N15 -161.2(4) . . . . ? O1A Nd O16 N15 -37.6(4) . . . . ? O13 Nd O16 N15 81.2(4) . . . . ? O17 Nd O16 N15 -2.9(3) . . . . ? O12 Nd O16 N15 139.9(3) . . . . ? N4A Nd O16 N15 23.7(4) . . . . ? N4B Nd O16 N15 135.5(4) . . . . ? N7A Nd O16 N15 76.1(3) . . . . ? O18 N15 O17 Nd 173.9(6) . . . . ? O16 N15 O17 Nd -4.9(5) . . . . ? O41 Nd O17 N15 82.3(3) . . . . ? O31 Nd O17 N15 120.7(4) . . . . ? O1B Nd O17 N15 26.1(4) . . . . ? O1A Nd O17 N15 152.9(3) . . . . ? O13 Nd O17 N15 -140.9(3) . . . . ? O16 Nd O17 N15 2.9(3) . . . . ? O12 Nd O17 N15 -79.0(4) . . . . ? N4A Nd O17 N15 -147.5(4) . . . . ? N4B Nd O17 N15 -33.4(3) . . . . ? N7A Nd O17 N15 -85.2(3) . . . . ? O41 Nd O31 C32 11.2(8) . . . . ? O1B Nd O31 C32 84.0(9) . . . . ? O1A Nd O31 C32 -60.0(8) . . . . ? O13 Nd O31 C32 -142.8(9) . . . . ? O16 Nd O31 C32 54.0(9) . . . . ? O17 Nd O31 C32 -26.3(10) . . . . ? O12 Nd O31 C32 164.8(9) . . . . ? N4A Nd O31 C32 -99.4(9) . . . . ? N4B Nd O31 C32 125.9(8) . . . . ? N7A Nd O31 C32 -167.8(8) . . . . ? Nd O31 C32 N33 -170.8(9) . . . . ? O31 C32 N33 C34 -178.2(10) . . . . ? O31 C32 N33 C35 -56.0(17) . . . . ? O31 Nd O41 C42 72.7(8) . . . . ? O1B Nd O41 C42 -1.6(8) . . . . ? O1A Nd O41 C42 146.1(8) . . . . ? O13 Nd O41 C42 110.6(8) . . . . ? O16 Nd O41 C42 -78.5(8) . . . . ? O17 Nd O41 C42 -129.6(8) . . . . ? O12 Nd O41 C42 36.3(9) . . . . ? N4A Nd O41 C42 -176.4(8) . . . . ? N4B Nd O41 C42 -36.9(8) . . . . ? N7A Nd O41 C42 -108.5(8) . . . . ? Nd O41 C42 N43 147.4(6) . . . . ? O41 C42 N43 C45 -4.5(10) . . . . ? O41 C42 N43 C44 178.2(6) . . . . ? O51 C52 N53 C54 -179.8(7) . . . . ? O51 C52 N53 C55 0.4(11) . . . . ? O61 C62 N63 C65 -166(2) . . . . ? O61 C62 N63 C64 5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 3.129 _refine_diff_density_min -1.658 _refine_diff_density_rms 0.149 # Attachment 'fro4558.cif' data_fro4558 _database_code_depnum_ccdc_archive 'CCDC 728925' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 Cl3 N6 Nd O5' _chemical_formula_weight 731.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3553(2) _cell_length_b 11.9533(3) _cell_length_c 16.6904(5) _cell_angle_alpha 77.925(1) _cell_angle_beta 74.020(1) _cell_angle_gamma 80.010(2) _cell_volume 1741.23(8) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4092 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 730 _exptl_absorpt_coefficient_mu 1.758 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5398 _exptl_absorpt_correction_T_max 0.7784 _exptl_absorpt_process_details 'Denzo (Otwinowski, Borek, Majewski & Mimor, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '\w and \f scans' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15738 _diffrn_reflns_av_R_equivalents 0.038 _diffrn_reflns_av_sigmaI/netI 0.0399 _diffrn_reflns_limit_h_min -12 _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 21 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 28.37 _reflns_number_total 8354 _reflns_number_gt 7311 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. DMF molecule heavily disordered, refined with split positions for the the CH3-groups, in addition geometrical (DFIX) and thermal (ISOR, SIMU) restraints were applied. Remaining density around 0,0,0 (about 2.5 e A-3, size of the void 353 A3) could not be refined in a chemically meanigful way, therefore the SQUEEZE routine from the PLATON suite (Spek, 1997) was used (see special part of CIF). ; _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^)+(0.0732P)^2^+8.4096P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at water from difmap, others geom' _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8354 _refine_ls_number_parameters 371 _refine_ls_number_restraints 73 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1585 _refine_ls_wR_factor_gt 0.1536 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.022 0.000 0.000 382 61 ' ' _platon_squeeze_details ; ; 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 Nd Nd 0.79279(3) 0.70684(3) 0.657492(18) 0.03224(11) Uani 1 1 d . . . Cl1 Cl 0.77648(15) 0.47083(12) 0.68117(8) 0.0362(3) Uani 1 1 d . . . O1A O 0.7148(4) 0.6896(4) 0.5270(2) 0.0416(10) Uani 1 1 d . . . C2A C 0.8028(6) 0.6784(5) 0.4581(3) 0.0336(11) Uani 1 1 d . . . C21A C 0.7503(7) 0.6935(5) 0.3799(4) 0.0382(12) Uani 1 1 d . . . C22A C 0.5991(8) 0.7308(7) 0.3854(4) 0.0529(17) Uani 1 1 d . . . H22A H 0.5346 0.7457 0.4373 0.063 Uiso 1 1 calc R . . C23A C 0.5436(9) 0.7461(9) 0.3143(5) 0.075(3) Uani 1 1 d . . . H23A H 0.4411 0.7701 0.3181 0.090 Uiso 1 1 calc R . . C24A C 0.6383(9) 0.7261(9) 0.2382(5) 0.071(3) Uani 1 1 d . . . H24A H 0.6008 0.7368 0.1900 0.085 Uiso 1 1 calc R . . C25A C 0.7876(9) 0.6907(8) 0.2326(4) 0.061(2) Uani 1 1 d . . . H25A H 0.8519 0.6781 0.1802 0.073 Uiso 1 1 calc R . . C26A C 0.8448(7) 0.6733(6) 0.3023(4) 0.0455(15) Uani 1 1 d . . . H26A H 0.9472 0.6478 0.2978 0.055 Uiso 1 1 calc R . . N3A N 0.9531(5) 0.6529(4) 0.4510(3) 0.0344(10) Uani 1 1 d . . . H3A H 1.0161 0.6432 0.4031 0.041 Uiso 1 1 calc R . . N4A N 0.9994(5) 0.6433(4) 0.5234(3) 0.0322(9) Uani 1 1 d . . . C5A C 1.1407(6) 0.6282(5) 0.5175(4) 0.0347(11) Uani 1 1 d . . . H5A H 1.2109 0.6237 0.4654 0.042 Uiso 1 1 calc R . . C6A C 1.1876(6) 0.6183(5) 0.5955(4) 0.0347(11) Uani 1 1 d . . . N7A N 1.0767(5) 0.6328(4) 0.6657(3) 0.0365(10) Uani 1 1 d . . . C8A C 1.3378(6) 0.5906(6) 0.5968(4) 0.0465(15) Uani 1 1 d . . . H8A H 1.4120 0.5835 0.5464 0.056 Uiso 1 1 calc R . . C9A C 1.3769(7) 0.5735(8) 0.6733(5) 0.0576(19) Uani 1 1 d . . . H9A H 1.4777 0.5550 0.6756 0.069 Uiso 1 1 calc R . . C8B C 1.2650(8) 0.5843(8) 0.7457(5) 0.0581(19) Uani 1 1 d . . . H8B H 1.2877 0.5728 0.7985 0.070 Uiso 1 1 calc R . . C6B C 1.1171(7) 0.6125(6) 0.7390(4) 0.0453(15) Uani 1 1 d . . . C5B C 0.9938(7) 0.6178(7) 0.8155(4) 0.0488(16) Uani 1 1 d . . . H5B H 1.0123 0.6078 0.8693 0.059 Uiso 1 1 calc R . . N4B N 0.8597(6) 0.6365(5) 0.8057(3) 0.0397(11) Uani 1 1 d . . . N3B N 0.7442(6) 0.6400(5) 0.8762(3) 0.0478(13) Uani 1 1 d . . . H3B H 0.7590 0.6284 0.9267 0.057 Uiso 1 1 calc R . . C2B C 0.6051(7) 0.6625(6) 0.8627(4) 0.0407(13) Uani 1 1 d . . . C21B C 0.4770(8) 0.6677(6) 0.9387(4) 0.0492(16) Uani 1 1 d . . . C22B C 0.3365(9) 0.7029(10) 0.9251(6) 0.080(3) Uani 1 1 d . . . H22B H 0.3235 0.7259 0.8699 0.095 Uiso 1 1 calc R . . C23B C 0.2135(12) 0.7038(15) 0.9952(10) 0.124(5) Uani 1 1 d . . . H23B H 0.1167 0.7279 0.9869 0.148 Uiso 1 1 calc R . . C24B C 0.2318(13) 0.6701(13) 1.0757(8) 0.113(5) Uani 1 1 d . . . H24B H 0.1480 0.6701 1.1223 0.136 Uiso 1 1 calc R . . C25B C 0.3685(13) 0.6374(10) 1.0876(6) 0.087(3) Uani 1 1 d . . . H25B H 0.3804 0.6156 1.1431 0.105 Uiso 1 1 calc R . . C26B C 0.4925(11) 0.6346(8) 1.0212(5) 0.071(2) Uani 1 1 d . . . H26B H 0.5881 0.6103 1.0312 0.086 Uiso 1 1 calc R . . O1B O 0.5872(5) 0.6806(4) 0.7904(3) 0.0457(10) Uani 1 1 d . . . Cl2 Cl 0.8549(4) 0.5917(5) 1.03657(19) 0.1405(17) Uani 1 1 d . . . Cl3 Cl 0.8218(4) 1.1122(2) 0.5921(3) 0.151(2) Uani 1 1 d . . . O1 O 0.8981(6) 0.8673(4) 0.5499(4) 0.0633(15) Uani 1 1 d D . . H11 H 0.8637 0.9265 0.5718 0.095 Uiso 1 1 d RD . . H12 H 0.9616 0.8829 0.5038 0.095 Uiso 1 1 d RD . . O2 O 0.8139(10) 0.8628(5) 0.7264(4) 0.091(2) Uani 1 1 d D . . H21 H 0.7611 0.8551 0.7765 0.136 Uiso 1 1 d RD . . H22 H 0.8484 0.9356 0.7131 0.136 Uiso 1 1 d RD . . O301 O 0.5747(6) 0.8381(5) 0.6403(3) 0.0615(14) Uani 1 1 d DU . . C302 C 0.4628(11) 0.8843(11) 0.6786(8) 0.125(5) Uani 1 1 d DU A . H302 H 0.4612 0.8867 0.7347 0.150 Uiso 1 1 calc R . . N303 N 0.3397(11) 0.9329(10) 0.6557(9) 0.132(4) Uani 1 1 d DU . . C304 C 0.210(6) 0.984(9) 0.712(3) 0.30(2) Uani 0.45(4) 1 d PDU A 1 H30A H 0.1205 0.9586 0.7066 0.447 Uiso 0.45(4) 1 calc PR A 1 H30B H 0.2032 1.0675 0.6967 0.447 Uiso 0.45(4) 1 calc PR A 1 H30C H 0.2191 0.9610 0.7696 0.447 Uiso 0.45(4) 1 calc PR A 1 C305 C 0.351(6) 0.963(7) 0.5649(13) 0.27(2) Uani 0.45(4) 1 d PDU A 1 H30D H 0.2705 1.0232 0.5547 0.403 Uiso 0.45(4) 1 calc PR A 1 H30E H 0.3421 0.8955 0.5436 0.403 Uiso 0.45(4) 1 calc PR A 1 H30F H 0.4465 0.9902 0.5360 0.403 Uiso 0.45(4) 1 calc PR A 1 C306 C 0.227(5) 0.995(7) 0.718(3) 0.296(19) Uani 0.55(4) 1 d PDU A 2 H30G H 0.2152 1.0765 0.6944 0.444 Uiso 0.55(4) 1 calc PR A 2 H30H H 0.2591 0.9837 0.7694 0.444 Uiso 0.55(4) 1 calc PR A 2 H30I H 0.1316 0.9652 0.7295 0.444 Uiso 0.55(4) 1 calc PR A 2 C307 C 0.271(6) 0.883(5) 0.605(4) 0.27(2) Uani 0.55(4) 1 d PDU A 2 H30J H 0.1669 0.8768 0.6336 0.401 Uiso 0.55(4) 1 calc PR A 2 H30K H 0.3237 0.8076 0.5968 0.401 Uiso 0.55(4) 1 calc PR A 2 H30L H 0.2771 0.9329 0.5502 0.401 Uiso 0.55(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Nd 0.02586(15) 0.04500(19) 0.02483(15) -0.00482(11) -0.00669(10) -0.00232(11) Cl1 0.0303(6) 0.0459(7) 0.0295(6) -0.0072(5) -0.0017(5) -0.0051(5) O1A 0.0274(19) 0.072(3) 0.0233(19) -0.0077(18) -0.0042(15) -0.0036(19) C2A 0.029(3) 0.044(3) 0.025(2) -0.004(2) -0.006(2) -0.002(2) C21A 0.035(3) 0.051(3) 0.028(3) -0.005(2) -0.010(2) -0.004(2) C22A 0.041(3) 0.082(5) 0.032(3) -0.009(3) -0.011(3) 0.005(3) C23A 0.049(4) 0.127(8) 0.049(4) -0.022(5) -0.025(4) 0.023(5) C24A 0.057(4) 0.125(8) 0.033(4) -0.016(4) -0.024(3) 0.011(5) C25A 0.057(4) 0.095(6) 0.029(3) -0.014(3) -0.014(3) 0.009(4) C26A 0.035(3) 0.069(4) 0.029(3) -0.008(3) -0.009(2) 0.005(3) N3A 0.027(2) 0.052(3) 0.022(2) -0.0057(19) -0.0034(17) -0.005(2) N4A 0.026(2) 0.042(3) 0.027(2) -0.0050(18) -0.0056(17) -0.0045(18) C5A 0.026(2) 0.043(3) 0.032(3) -0.006(2) -0.002(2) -0.005(2) C6A 0.024(2) 0.045(3) 0.036(3) -0.009(2) -0.006(2) -0.003(2) N7A 0.028(2) 0.048(3) 0.036(3) -0.007(2) -0.0120(19) -0.005(2) C8A 0.023(3) 0.067(4) 0.049(4) -0.015(3) -0.006(2) -0.005(3) C9A 0.027(3) 0.088(6) 0.066(5) -0.022(4) -0.019(3) -0.003(3) C8B 0.037(3) 0.092(6) 0.054(4) -0.021(4) -0.025(3) 0.003(3) C6B 0.033(3) 0.069(4) 0.038(3) -0.013(3) -0.016(2) 0.000(3) C5B 0.037(3) 0.082(5) 0.028(3) -0.013(3) -0.014(2) 0.004(3) N4B 0.034(2) 0.057(3) 0.027(2) -0.006(2) -0.0085(19) -0.001(2) N3B 0.037(3) 0.078(4) 0.022(2) -0.005(2) -0.003(2) 0.000(3) C2B 0.037(3) 0.056(4) 0.025(3) -0.010(2) -0.002(2) 0.000(3) C21B 0.042(3) 0.064(4) 0.035(3) -0.016(3) 0.009(3) -0.009(3) C22B 0.044(4) 0.132(9) 0.062(5) -0.037(5) 0.006(4) -0.014(5) C23B 0.046(5) 0.205(16) 0.116(11) -0.065(11) 0.013(6) -0.012(7) C24B 0.074(7) 0.172(13) 0.092(9) -0.070(9) 0.041(6) -0.052(8) C25B 0.094(8) 0.109(8) 0.043(5) -0.025(5) 0.024(5) -0.023(6) C26B 0.074(6) 0.085(6) 0.036(4) -0.007(4) 0.013(4) -0.007(5) O1B 0.034(2) 0.068(3) 0.031(2) -0.010(2) -0.0057(17) 0.002(2) Cl2 0.111(2) 0.267(5) 0.0558(15) -0.024(2) -0.0265(16) -0.050(3) Cl3 0.128(3) 0.0656(15) 0.192(4) -0.0461(19) 0.100(3) -0.0288(16) O1 0.047(3) 0.044(3) 0.078(4) -0.002(2) 0.013(3) -0.007(2) O2 0.155(7) 0.061(4) 0.073(4) -0.014(3) -0.056(5) -0.010(4) O301 0.051(3) 0.075(3) 0.050(3) -0.012(2) -0.015(2) 0.022(2) C302 0.100(7) 0.110(7) 0.123(8) 0.024(6) -0.016(6) 0.027(6) N303 0.094(6) 0.086(6) 0.198(9) -0.012(6) -0.024(6) 0.006(5) C304 0.29(2) 0.29(2) 0.30(2) -0.045(10) -0.063(10) -0.033(9) C305 0.28(2) 0.27(2) 0.27(2) -0.055(10) -0.073(11) -0.035(9) C306 0.29(2) 0.29(2) 0.30(2) -0.045(10) -0.063(10) -0.033(9) C307 0.27(2) 0.27(2) 0.26(2) -0.046(10) -0.073(11) -0.037(9) _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 Nd O301 2.393(5) . ? Nd O2 2.446(6) . ? Nd O1 2.473(5) . ? Nd O1B 2.508(4) . ? Nd O1A 2.536(4) . ? Nd N4B 2.649(5) . ? Nd N4A 2.672(4) . ? Nd N7A 2.682(5) . ? Nd Cl1 2.7907(15) . ? O1A C2A 1.235(7) . ? C2A N3A 1.363(7) . ? C2A C21A 1.484(7) . ? C21A C22A 1.390(9) . ? C21A C26A 1.394(8) . ? C22A C23A 1.390(9) . ? C22A H22A 0.9400 . ? C23A C24A 1.375(11) . ? C23A H23A 0.9400 . ? C24A C25A 1.370(11) . ? C24A H24A 0.9400 . ? C25A C26A 1.374(9) . ? C25A H25A 0.9400 . ? C26A H26A 0.9400 . ? N3A N4A 1.369(6) . ? N3A H3A 0.8700 . ? N4A C5A 1.281(7) . ? C5A C6A 1.460(8) . ? C5A H5A 0.9400 . ? C6A N7A 1.353(7) . ? C6A C8A 1.392(8) . ? N7A C6B 1.340(7) . ? C8A C9A 1.388(10) . ? C8A H8A 0.9400 . ? C9A C8B 1.377(11) . ? C9A H9A 0.9400 . ? C8B C6B 1.396(8) . ? C8B H8B 0.9400 . ? C6B C5B 1.471(9) . ? C5B N4B 1.285(8) . ? C5B H5B 0.9400 . ? N4B N3B 1.364(7) . ? N3B C2B 1.353(8) . ? N3B H3B 0.8700 . ? C2B O1B 1.233(7) . ? C2B C21B 1.490(8) . ? C21B C22B 1.375(12) . ? C21B C26B 1.390(11) . ? C22B C23B 1.397(14) . ? C22B H22B 0.9400 . ? C23B C24B 1.37(2) . ? C23B H23B 0.9400 . ? C24B C25B 1.328(18) . ? C24B H24B 0.9400 . ? C25B C26B 1.368(11) . ? C25B H25B 0.9400 . ? C26B H26B 0.9400 . ? O1 H11 0.8382 . ? O1 H12 0.8408 . ? O2 H21 0.8410 . ? O2 H22 0.9433 . ? O301 C302 1.178(8) . ? C302 N303 1.313(8) . ? C302 H302 0.9400 . ? N303 C304 1.442(9) . ? N303 C307 1.458(10) . ? N303 C305 1.462(10) . ? N303 C306 1.476(10) . ? C304 H30A 0.9700 . ? C304 H30B 0.9700 . ? C304 H30C 0.9700 . ? C305 H30D 0.9700 . ? C305 H30E 0.9700 . ? C305 H30F 0.9700 . ? C306 H30G 0.9700 . ? C306 H30H 0.9700 . ? C306 H30I 0.9700 . ? C307 H30J 0.9700 . ? C307 H30K 0.9700 . ? C307 H30L 0.9700 . ? 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 O301 Nd O2 78.3(2) . . ? O301 Nd O1 77.02(19) . . ? O2 Nd O1 70.0(2) . . ? O301 Nd O1B 70.17(17) . . ? O2 Nd O1B 78.2(2) . . ? O1 Nd O1B 138.08(16) . . ? O301 Nd O1A 68.32(16) . . ? O2 Nd O1A 136.80(19) . . ? O1 Nd O1A 76.23(18) . . ? O1B Nd O1A 113.14(14) . . ? O301 Nd N4B 122.58(16) . . ? O2 Nd N4B 65.68(19) . . ? O1 Nd N4B 124.43(19) . . ? O1B Nd N4B 60.08(14) . . ? O1A Nd N4B 156.95(17) . . ? O301 Nd N4A 120.91(16) . . ? O2 Nd N4A 123.1(2) . . ? O1 Nd N4A 64.90(16) . . ? O1B Nd N4A 156.29(16) . . ? O1A Nd N4A 60.11(13) . . ? N4B Nd N4A 116.13(14) . . ? O301 Nd N7A 159.18(19) . . ? O2 Nd N7A 85.2(2) . . ? O1 Nd N7A 85.53(17) . . ? O1B Nd N7A 118.87(14) . . ? O1A Nd N7A 118.64(14) . . ? N4B Nd N7A 59.43(15) . . ? N4A Nd N7A 59.07(14) . . ? O301 Nd Cl1 118.44(16) . . ? O2 Nd Cl1 144.11(16) . . ? O1 Nd Cl1 141.54(13) . . ? O1B Nd Cl1 78.72(12) . . ? O1A Nd Cl1 77.98(11) . . ? N4B Nd Cl1 79.04(12) . . ? N4A Nd Cl1 77.61(11) . . ? N7A Nd Cl1 82.33(11) . . ? C2A O1A Nd 124.4(4) . . ? O1A C2A N3A 120.8(5) . . ? O1A C2A C21A 121.7(5) . . ? N3A C2A C21A 117.5(5) . . ? C22A C21A C26A 119.4(5) . . ? C22A C21A C2A 117.4(5) . . ? C26A C21A C2A 123.2(5) . . ? C23A C22A C21A 119.9(6) . . ? C23A C22A H22A 120.1 . . ? C21A C22A H22A 120.1 . . ? C24A C23A C22A 120.1(7) . . ? C24A C23A H23A 120.0 . . ? C22A C23A H23A 120.0 . . ? C25A C24A C23A 120.0(6) . . ? C25A C24A H24A 120.0 . . ? C23A C24A H24A 120.0 . . ? C24A C25A C26A 121.1(7) . . ? C24A C25A H25A 119.5 . . ? C26A C25A H25A 119.5 . . ? C25A C26A C21A 119.7(6) . . ? C25A C26A H26A 120.2 . . ? C21A C26A H26A 120.2 . . ? C2A N3A N4A 116.5(4) . . ? C2A N3A H3A 121.8 . . ? N4A N3A H3A 121.8 . . ? C5A N4A N3A 117.9(5) . . ? C5A N4A Nd 123.9(4) . . ? N3A N4A Nd 116.6(3) . . ? N4A C5A C6A 116.9(5) . . ? N4A C5A H5A 121.5 . . ? C6A C5A H5A 121.5 . . ? N7A C6A C8A 122.9(5) . . ? N7A C6A C5A 116.2(5) . . ? C8A C6A C5A 120.9(5) . . ? C6B N7A C6A 116.6(5) . . ? C6B N7A Nd 121.7(4) . . ? C6A N7A Nd 121.6(4) . . ? C9A C8A C6A 119.2(6) . . ? C9A C8A H8A 120.4 . . ? C6A C8A H8A 120.4 . . ? C8B C9A C8A 118.7(6) . . ? C8B C9A H9A 120.7 . . ? C8A C9A H9A 120.7 . . ? C9A C8B C6B 118.5(6) . . ? C9A C8B H8B 120.7 . . ? C6B C8B H8B 120.7 . . ? N7A C6B C8B 124.0(6) . . ? N7A C6B C5B 115.9(5) . . ? C8B C6B C5B 120.1(6) . . ? N4B C5B C6B 117.1(5) . . ? N4B C5B H5B 121.5 . . ? C6B C5B H5B 121.5 . . ? C5B N4B N3B 117.8(5) . . ? C5B N4B Nd 124.2(4) . . ? N3B N4B Nd 117.0(3) . . ? C2B N3B N4B 115.8(5) . . ? C2B N3B H3B 122.1 . . ? N4B N3B H3B 122.1 . . ? O1B C2B N3B 120.9(5) . . ? O1B C2B C21B 122.3(6) . . ? N3B C2B C21B 116.8(5) . . ? C22B C21B C26B 119.4(7) . . ? C22B C21B C2B 117.1(7) . . ? C26B C21B C2B 123.4(7) . . ? C21B C22B C23B 118.4(10) . . ? C21B C22B H22B 120.8 . . ? C23B C22B H22B 120.8 . . ? C24B C23B C22B 121.0(12) . . ? C24B C23B H23B 119.5 . . ? C22B C23B H23B 119.5 . . ? C25B C24B C23B 119.6(9) . . ? C25B C24B H24B 120.2 . . ? C23B C24B H24B 120.2 . . ? C24B C25B C26B 121.6(11) . . ? C24B C25B H25B 119.2 . . ? C26B C25B H25B 119.2 . . ? C25B C26B C21B 119.9(10) . . ? C25B C26B H26B 120.1 . . ? C21B C26B H26B 120.1 . . ? C2B O1B Nd 124.9(4) . . ? Nd O1 H11 105.1 . . ? Nd O1 H12 143.6 . . ? H11 O1 H12 110.7 . . ? Nd O2 H21 110.6 . . ? Nd O2 H22 140.5 . . ? H21 O2 H22 107.9 . . ? C302 O301 Nd 142.6(7) . . ? O301 C302 N303 130.7(12) . . ? O301 C302 H302 114.7 . . ? N303 C302 H302 114.7 . . ? C302 N303 C304 123.6(16) . . ? C302 N303 C307 123(2) . . ? C304 N303 C307 102(5) . . ? C302 N303 C305 116.8(15) . . ? C304 N303 C305 117.6(15) . . ? C307 N303 C305 52(3) . . ? C302 N303 C306 116.0(13) . . ? C304 N303 C306 10(6) . . ? C307 N303 C306 111.9(16) . . ? C305 N303 C306 122(3) . . ? N303 C304 H30A 109.5 . . ? N303 C304 H30B 109.5 . . ? H30A C304 H30B 109.5 . . ? N303 C304 H30C 109.5 . . ? H30A C304 H30C 109.5 . . ? H30B C304 H30C 109.5 . . ? N303 C305 H30D 109.5 . . ? N303 C305 H30E 109.5 . . ? H30D C305 H30E 109.5 . . ? N303 C305 H30F 109.5 . . ? H30D C305 H30F 109.5 . . ? H30E C305 H30F 109.5 . . ? N303 C306 H30G 109.5 . . ? N303 C306 H30H 109.5 . . ? H30G C306 H30H 109.5 . . ? N303 C306 H30I 109.5 . . ? H30G C306 H30I 109.5 . . ? H30H C306 H30I 109.5 . . ? N303 C307 H30J 109.5 . . ? N303 C307 H30K 109.5 . . ? H30J C307 H30K 109.5 . . ? N303 C307 H30L 109.5 . . ? H30J C307 H30L 109.5 . . ? H30K C307 H30L 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O301 Nd O1A C2A 138.4(5) . . . . ? O2 Nd O1A C2A 96.4(6) . . . . ? O1 Nd O1A C2A 57.1(5) . . . . ? O1B Nd O1A C2A -166.1(5) . . . . ? N4B Nd O1A C2A -98.5(6) . . . . ? N4A Nd O1A C2A -11.6(5) . . . . ? N7A Nd O1A C2A -19.9(5) . . . . ? Cl1 Nd O1A C2A -94.1(5) . . . . ? Nd O1A C2A N3A 12.3(8) . . . . ? Nd O1A C2A C21A -166.8(4) . . . . ? O1A C2A C21A C22A 5.4(10) . . . . ? N3A C2A C21A C22A -173.7(6) . . . . ? O1A C2A C21A C26A -175.2(6) . . . . ? N3A C2A C21A C26A 5.7(9) . . . . ? C26A C21A C22A C23A 0.8(12) . . . . ? C2A C21A C22A C23A -179.7(8) . . . . ? C21A C22A C23A C24A -1.1(15) . . . . ? C22A C23A C24A C25A 0.3(17) . . . . ? C23A C24A C25A C26A 0.7(16) . . . . ? C24A C25A C26A C21A -1.0(13) . . . . ? C22A C21A C26A C25A 0.2(11) . . . . ? C2A C21A C26A C25A -179.2(7) . . . . ? O1A C2A N3A N4A -1.4(8) . . . . ? C21A C2A N3A N4A 177.8(5) . . . . ? C2A N3A N4A C5A -174.7(5) . . . . ? C2A N3A N4A Nd -8.8(6) . . . . ? O301 Nd N4A C5A 141.9(5) . . . . ? O2 Nd N4A C5A 45.7(5) . . . . ? O1 Nd N4A C5A 86.6(5) . . . . ? O1B Nd N4A C5A -105.8(5) . . . . ? O1A Nd N4A C5A 174.7(5) . . . . ? N4B Nd N4A C5A -31.1(5) . . . . ? N7A Nd N4A C5A -13.8(4) . . . . ? Cl1 Nd N4A C5A -102.2(5) . . . . ? O301 Nd N4A N3A -23.1(4) . . . . ? O2 Nd N4A N3A -119.3(4) . . . . ? O1 Nd N4A N3A -78.4(4) . . . . ? O1B Nd N4A N3A 89.2(5) . . . . ? O1A Nd N4A N3A 9.7(3) . . . . ? N4B Nd N4A N3A 163.9(4) . . . . ? N7A Nd N4A N3A -178.7(4) . . . . ? Cl1 Nd N4A N3A 92.8(4) . . . . ? N3A N4A C5A C6A 180.0(5) . . . . ? Nd N4A C5A C6A 15.2(7) . . . . ? N4A C5A C6A N7A -3.7(8) . . . . ? N4A C5A C6A C8A 173.7(6) . . . . ? C8A C6A N7A C6B -3.8(9) . . . . ? C5A C6A N7A C6B 173.6(6) . . . . ? C8A C6A N7A Nd 173.7(5) . . . . ? C5A C6A N7A Nd -8.9(7) . . . . ? O301 Nd N7A C6B 92.1(7) . . . . ? O2 Nd N7A C6B 54.7(5) . . . . ? O1 Nd N7A C6B 125.1(5) . . . . ? O1B Nd N7A C6B -19.0(6) . . . . ? O1A Nd N7A C6B -163.3(5) . . . . ? N4B Nd N7A C6B -9.8(5) . . . . ? N4A Nd N7A C6B -171.6(6) . . . . ? Cl1 Nd N7A C6B -91.5(5) . . . . ? O301 Nd N7A C6A -85.3(6) . . . . ? O2 Nd N7A C6A -122.6(5) . . . . ? O1 Nd N7A C6A -52.3(5) . . . . ? O1B Nd N7A C6A 163.6(4) . . . . ? O1A Nd N7A C6A 19.3(5) . . . . ? N4B Nd N7A C6A 172.8(5) . . . . ? N4A Nd N7A C6A 11.0(4) . . . . ? Cl1 Nd N7A C6A 91.1(4) . . . . ? N7A C6A C8A C9A 2.0(10) . . . . ? C5A C6A C8A C9A -175.3(7) . . . . ? C6A C8A C9A C8B 0.2(12) . . . . ? C8A C9A C8B C6B -0.3(13) . . . . ? C6A N7A C6B C8B 3.7(10) . . . . ? Nd N7A C6B C8B -173.8(6) . . . . ? C6A N7A C6B C5B -174.3(6) . . . . ? Nd N7A C6B C5B 8.2(8) . . . . ? C9A C8B C6B N7A -1.7(13) . . . . ? C9A C8B C6B C5B 176.2(8) . . . . ? N7A C6B C5B N4B 2.7(10) . . . . ? C8B C6B C5B N4B -175.4(7) . . . . ? C6B C5B N4B N3B 179.1(6) . . . . ? C6B C5B N4B Nd -12.8(9) . . . . ? O301 Nd N4B C5B -143.8(6) . . . . ? O2 Nd N4B C5B -87.4(6) . . . . ? O1 Nd N4B C5B -47.2(6) . . . . ? O1B Nd N4B C5B -177.5(6) . . . . ? O1A Nd N4B C5B 103.7(6) . . . . ? N4A Nd N4B C5B 29.1(6) . . . . ? N7A Nd N4B C5B 11.8(5) . . . . ? Cl1 Nd N4B C5B 99.3(6) . . . . ? O301 Nd N4B N3B 24.3(5) . . . . ? O2 Nd N4B N3B 80.7(5) . . . . ? O1 Nd N4B N3B 120.9(4) . . . . ? O1B Nd N4B N3B -9.3(4) . . . . ? O1A Nd N4B N3B -88.1(6) . . . . ? N4A Nd N4B N3B -162.7(4) . . . . ? N7A Nd N4B N3B 180.0(5) . . . . ? Cl1 Nd N4B N3B -92.5(5) . . . . ? C5B N4B N3B C2B 178.6(7) . . . . ? Nd N4B N3B C2B 9.6(8) . . . . ? N4B N3B C2B O1B -1.3(10) . . . . ? N4B N3B C2B C21B -179.5(6) . . . . ? O1B C2B C21B C22B -5.2(11) . . . . ? N3B C2B C21B C22B 173.0(8) . . . . ? O1B C2B C21B C26B 172.1(8) . . . . ? N3B C2B C21B C26B -9.6(11) . . . . ? C26B C21B C22B C23B -0.2(16) . . . . ? C2B C21B C22B C23B 177.3(10) . . . . ? C21B C22B C23B C24B 0(2) . . . . ? C22B C23B C24B C25B 1(2) . . . . ? C23B C24B C25B C26B -1(2) . . . . ? C24B C25B C26B C21B 0.7(17) . . . . ? C22B C21B C26B C25B 0.0(14) . . . . ? C2B C21B C26B C25B -177.3(8) . . . . ? N3B C2B O1B Nd -9.0(9) . . . . ? C21B C2B O1B Nd 169.2(5) . . . . ? O301 Nd O1B C2B -140.6(6) . . . . ? O2 Nd O1B C2B -58.9(5) . . . . ? O1 Nd O1B C2B -99.9(6) . . . . ? O1A Nd O1B C2B 165.0(5) . . . . ? N4B Nd O1B C2B 9.7(5) . . . . ? N4A Nd O1B C2B 97.0(6) . . . . ? N7A Nd O1B C2B 18.8(6) . . . . ? Cl1 Nd O1B C2B 93.4(5) . . . . ? O2 Nd O301 C302 -60.0(15) . . . . ? O1 Nd O301 C302 -132.0(15) . . . . ? O1B Nd O301 C302 21.5(15) . . . . ? O1A Nd O301 C302 147.9(15) . . . . ? N4B Nd O301 C302 -9.2(15) . . . . ? N4A Nd O301 C302 178.2(14) . . . . ? N7A Nd O301 C302 -98.2(15) . . . . ? Cl1 Nd O301 C302 85.9(15) . . . . ? Nd O301 C302 N303 -160.9(10) . . . . ? O301 C302 N303 C304 179(6) . . . . ? O301 C302 N303 C307 42(4) . . . . ? O301 C302 N303 C305 -18(5) . . . . ? O301 C302 N303 C306 -173(4) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 28.37 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 2.715 _refine_diff_density_min -2.126 _refine_diff_density_rms 0.150 # Attachment 'fro4565.cif' data_fro4565 _database_code_depnum_ccdc_archive 'CCDC 728926' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 Cl3 La N5 O6' _chemical_formula_weight 688.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.5637(1) _cell_length_b 11.5476(1) _cell_length_c 22.9725(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.088(1) _cell_angle_gamma 90.00 _cell_volume 2767.13(5) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 5030 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 27.88 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 1.877 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6512 _exptl_absorpt_correction_T_max 0.8345 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995 & 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16489 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0452 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 27.93 _reflns_number_total 6613 _reflns_number_gt 5330 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SCHAKAL (Keller, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Remaining electron density in the region of O4, probably a different solvent is partially place there, but could not be refined in a chemically meaningful way. ; _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^)+(0.0834P)^2^+8.2599P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'at water and N from difmap, others geom' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6613 _refine_ls_number_parameters 355 _refine_ls_number_restraints 34 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1440 _refine_ls_wR_factor_gt 0.1329 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.021 _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 La La 1.09044(2) 0.19215(2) 0.889676(12) 0.02405(11) Uani 1 1 d . . . O1 O 0.9566(4) 0.1097(4) 0.9652(2) 0.0472(10) Uani 1 1 d D . . H11 H 0.886(5) 0.078(5) 0.940(3) 0.071 Uiso 1 1 d D . . H12 H 1.004(6) 0.066(5) 0.996(3) 0.071 Uiso 1 1 d D . . O2 O 1.0288(4) 0.3723(3) 0.94607(17) 0.0424(9) Uani 1 1 d D . . H21 H 1.059(6) 0.388(6) 0.9865(15) 0.064 Uiso 1 1 d D . . H22 H 0.952(4) 0.407(6) 0.927(3) 0.064 Uiso 1 1 d D . . O3 O 1.2126(4) 0.2066(3) 0.99738(17) 0.0369(9) Uani 1 1 d D . . H31 H 1.246(6) 0.143(4) 1.021(2) 0.055 Uiso 1 1 d D . . H32 H 1.233(7) 0.284(3) 1.010(3) 0.055 Uiso 1 1 d D . . O4 O 0.9346(4) 0.0184(4) 0.8452(2) 0.0467(10) Uani 1 1 d D . . H41 H 0.942(7) -0.063(3) 0.840(3) 0.070 Uiso 1 1 d D . . H42 H 0.864(5) 0.050(5) 0.860(3) 0.070 Uiso 1 1 d D . . Cl1 Cl 1.14589(12) 0.13942(11) 0.77481(6) 0.0362(3) Uani 1 1 d . . . O1A O 1.1784(3) -0.0083(3) 0.91721(17) 0.0328(8) Uani 1 1 d . . . C2A C 1.2908(5) -0.0422(4) 0.9254(2) 0.0272(10) Uani 1 1 d . . . C21A C 1.3238(5) -0.1640(4) 0.9405(2) 0.0283(10) Uani 1 1 d . . . C22A C 1.4476(5) -0.2069(4) 0.9496(3) 0.0343(11) Uani 1 1 d . . . H22A H 1.5166 -0.1584 0.9446 0.041 Uiso 1 1 calc R . . C23A C 1.4699(6) -0.3215(5) 0.9660(3) 0.0435(14) Uani 1 1 d . . . H23A H 1.5540 -0.3507 0.9719 0.052 Uiso 1 1 calc R . . C24A C 1.3692(6) -0.3929(5) 0.9736(3) 0.0436(14) Uani 1 1 d . . . H24A H 1.3852 -0.4698 0.9861 0.052 Uiso 1 1 calc R . . C25A C 1.2450(6) -0.3519(5) 0.9631(3) 0.0507(16) Uani 1 1 d . . . H25A H 1.1764 -0.4017 0.9668 0.061 Uiso 1 1 calc R . . C26A C 1.2216(6) -0.2388(5) 0.9472(3) 0.0511(17) Uani 1 1 d . . . H26A H 1.1369 -0.2109 0.9407 0.061 Uiso 1 1 calc R . . N3A N 1.3868(4) 0.0336(4) 0.9221(2) 0.0288(9) Uani 1 1 d . . . H3A H 1.451(6) 0.016(5) 0.921(3) 0.035 Uiso 1 1 d . . . N4A N 1.3507(4) 0.1440(3) 0.90456(18) 0.0265(8) Uani 1 1 d . . . C5A C 1.4385(4) 0.2196(4) 0.9041(2) 0.0272(10) Uani 1 1 d . . . H5A H 1.5250 0.2014 0.9174 0.033 Uiso 1 1 calc R . . C6A C 1.4011(4) 0.3355(4) 0.8822(2) 0.0256(9) Uani 1 1 d . . . N7A N 1.2744(4) 0.3538(3) 0.86502(17) 0.0252(8) Uani 1 1 d . . . C8A C 1.4933(5) 0.4172(4) 0.8752(2) 0.0317(10) Uani 1 1 d . . . H8A H 1.5803 0.4026 0.8891 0.038 Uiso 1 1 calc R . . C9A C 1.4561(5) 0.5204(5) 0.8474(2) 0.0350(11) Uani 1 1 d . . . H9A H 1.5172 0.5775 0.8427 0.042 Uiso 1 1 calc R . . C8B C 1.3298(5) 0.5385(5) 0.8268(3) 0.0368(12) Uani 1 1 d . . . H8B H 1.3028 0.6067 0.8062 0.044 Uiso 1 1 calc R . . C6B C 1.2400(5) 0.4537(4) 0.8367(2) 0.0295(10) Uani 1 1 d . . . C5B C 1.1041(5) 0.4676(4) 0.8123(2) 0.0327(11) Uani 1 1 d . . . H5B H 1.0747 0.5343 0.7909 0.039 Uiso 1 1 calc R . . N4B N 1.0266(4) 0.3870(3) 0.82097(18) 0.0262(8) Uani 1 1 d . . . N3B N 0.9014(4) 0.3974(4) 0.7953(2) 0.0302(9) Uani 1 1 d . . . H3B H 0.881(6) 0.453(5) 0.778(3) 0.036 Uiso 1 1 d . . . C2B C 0.8212(5) 0.3140(4) 0.8081(2) 0.0298(10) Uani 1 1 d . . . C21B C 0.6874(5) 0.3138(4) 0.7767(2) 0.0288(10) Uani 1 1 d . . . C22B C 0.6387(5) 0.3957(5) 0.7344(3) 0.0387(12) Uani 1 1 d . . . H22B H 0.6919 0.4552 0.7242 0.046 Uiso 1 1 calc R . . C23B C 0.5123(6) 0.3894(6) 0.7076(3) 0.0468(14) Uani 1 1 d . . . H23B H 0.4796 0.4455 0.6795 0.056 Uiso 1 1 calc R . . C24B C 0.4339(6) 0.3021(5) 0.7213(3) 0.0433(14) Uani 1 1 d . . . H24B H 0.3479 0.2989 0.7029 0.052 Uiso 1 1 calc R . . C25B C 0.4813(5) 0.2195(5) 0.7620(3) 0.0408(13) Uani 1 1 d . . . H25B H 0.4279 0.1591 0.7709 0.049 Uiso 1 1 calc R . . C26B C 0.6069(5) 0.2247(5) 0.7898(2) 0.0330(11) Uani 1 1 d . . . H26B H 0.6385 0.1681 0.8177 0.040 Uiso 1 1 calc R . . O1B O 0.8601(3) 0.2378(3) 0.84413(18) 0.0398(9) Uani 1 1 d . . . Cl12 Cl 0.68849(11) 0.00735(11) 0.92259(6) 0.0356(3) Uani 1 1 d . . . Cl11 Cl 0.8352(2) 0.57984(16) 0.92413(8) 0.0656(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 La 0.02068(15) 0.02186(16) 0.03000(16) 0.00504(10) 0.00520(10) 0.00463(9) O1 0.037(2) 0.055(3) 0.051(2) 0.009(2) 0.0095(18) -0.0103(19) O2 0.060(3) 0.033(2) 0.033(2) -0.0037(17) 0.0045(18) 0.0162(18) O3 0.036(2) 0.036(2) 0.036(2) -0.0014(16) -0.0022(16) 0.0093(16) O4 0.038(2) 0.041(2) 0.061(3) -0.005(2) 0.0084(19) -0.0070(18) Cl1 0.0367(6) 0.0354(7) 0.0365(6) -0.0098(5) 0.0058(5) -0.0037(5) O1A 0.0236(17) 0.0265(17) 0.048(2) 0.0076(16) 0.0048(15) 0.0047(13) C2A 0.027(2) 0.023(2) 0.032(2) 0.0005(19) 0.0051(19) -0.0006(18) C21A 0.026(2) 0.022(2) 0.037(3) -0.001(2) 0.0040(19) 0.0045(18) C22A 0.028(3) 0.026(2) 0.047(3) 0.004(2) -0.001(2) 0.0034(19) C23A 0.040(3) 0.026(3) 0.061(4) 0.005(3) -0.003(3) 0.010(2) C24A 0.058(4) 0.024(3) 0.048(3) 0.003(2) 0.005(3) 0.006(2) C25A 0.049(4) 0.030(3) 0.078(5) 0.005(3) 0.025(3) 0.002(3) C26A 0.037(3) 0.034(3) 0.087(5) 0.012(3) 0.022(3) 0.004(2) N3A 0.0224(19) 0.0228(19) 0.042(2) 0.0040(18) 0.0080(18) 0.0076(16) N4A 0.0254(19) 0.0236(19) 0.031(2) 0.0043(16) 0.0051(16) 0.0051(16) C5A 0.022(2) 0.029(2) 0.030(2) 0.002(2) 0.0030(18) 0.0047(18) C6A 0.024(2) 0.026(2) 0.028(2) 0.0019(19) 0.0065(18) 0.0010(18) N7A 0.0264(19) 0.0181(18) 0.031(2) 0.0024(16) 0.0034(16) -0.0003(15) C8A 0.024(2) 0.032(3) 0.040(3) -0.001(2) 0.006(2) -0.001(2) C9A 0.033(3) 0.033(3) 0.040(3) 0.003(2) 0.008(2) -0.010(2) C8B 0.037(3) 0.027(3) 0.047(3) 0.010(2) 0.007(2) -0.004(2) C6B 0.028(2) 0.027(2) 0.034(2) 0.004(2) 0.0038(19) -0.0034(19) C5B 0.031(3) 0.025(2) 0.040(3) 0.009(2) 0.003(2) 0.0039(19) N4B 0.0227(19) 0.0234(19) 0.031(2) 0.0050(16) -0.0004(15) 0.0029(15) N3B 0.024(2) 0.028(2) 0.037(2) 0.0077(18) -0.0013(17) 0.0049(16) C2B 0.027(2) 0.026(2) 0.036(3) 0.003(2) 0.005(2) 0.0020(18) C21B 0.027(2) 0.028(2) 0.031(2) 0.000(2) 0.0047(19) 0.0023(18) C22B 0.030(3) 0.040(3) 0.044(3) 0.013(2) 0.000(2) -0.003(2) C23B 0.036(3) 0.055(4) 0.045(3) 0.008(3) -0.009(2) -0.002(3) C24B 0.027(3) 0.060(4) 0.041(3) -0.009(3) -0.002(2) -0.001(2) C25B 0.031(3) 0.044(3) 0.048(3) -0.010(3) 0.010(2) -0.006(2) C26B 0.030(2) 0.034(3) 0.036(3) -0.001(2) 0.009(2) -0.001(2) O1B 0.0288(18) 0.036(2) 0.052(2) 0.0181(18) -0.0019(17) -0.0022(16) Cl12 0.0243(6) 0.0367(7) 0.0442(7) 0.0049(6) 0.0007(5) 0.0025(5) Cl11 0.0926(14) 0.0526(10) 0.0468(9) -0.0076(8) -0.0038(9) 0.0300(9) _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 La O1A 2.536(3) . ? La O1B 2.548(4) . ? La O1 2.586(4) . ? La O2 2.588(4) . ? La O3 2.609(4) . ? La O4 2.692(4) . ? La N4B 2.770(4) . ? La N4A 2.773(4) . ? La N7A 2.816(4) . ? La Cl1 2.8576(13) . ? O1 H11 0.95(3) . ? O1 H12 0.95(3) . ? O2 H21 0.95(3) . ? O2 H22 0.95(3) . ? O3 H31 0.95(3) . ? O3 H32 0.95(3) . ? O4 H41 0.96(3) . ? O4 H42 0.95(3) . ? O1A C2A 1.237(6) . ? C2A N3A 1.351(6) . ? C2A C21A 1.477(7) . ? C21A C22A 1.384(7) . ? C21A C26A 1.410(8) . ? C22A C23A 1.386(7) . ? C22A H22A 0.9400 . ? C23A C24A 1.379(9) . ? C23A H23A 0.9400 . ? C24A C25A 1.380(9) . ? C24A H24A 0.9400 . ? C25A C26A 1.367(9) . ? C25A H25A 0.9400 . ? C26A H26A 0.9400 . ? N3A N4A 1.373(6) . ? N3A H3A 0.71(6) . ? N4A C5A 1.275(6) . ? C5A C6A 1.461(7) . ? C5A H5A 0.9400 . ? C6A N7A 1.351(6) . ? C6A C8A 1.385(7) . ? N7A C6B 1.345(6) . ? C8A C9A 1.379(8) . ? C8A H8A 0.9400 . ? C9A C8B 1.360(8) . ? C9A H9A 0.9400 . ? C8B C6B 1.406(7) . ? C8B H8B 0.9400 . ? C6B C5B 1.466(7) . ? C5B N4B 1.275(6) . ? C5B H5B 0.9400 . ? N4B N3B 1.366(5) . ? N3B C2B 1.345(6) . ? N3B H3B 0.78(6) . ? C2B O1B 1.234(6) . ? C2B C21B 1.482(7) . ? C21B C22B 1.394(7) . ? C21B C26B 1.397(7) . ? C22B C23B 1.382(8) . ? C22B H22B 0.9400 . ? C23B C24B 1.373(9) . ? C23B H23B 0.9400 . ? C24B C25B 1.373(9) . ? C24B H24B 0.9400 . ? C25B C26B 1.381(8) . ? C25B H25B 0.9400 . ? C26B H26B 0.9400 . ? 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 O1A La O1B 125.43(12) . . ? O1A La O1 73.39(13) . . ? O1B La O1 76.33(13) . . ? O1A La O2 136.05(12) . . ? O1B La O2 74.91(14) . . ? O1 La O2 75.71(14) . . ? O1A La O3 73.46(12) . . ? O1B La O3 132.33(13) . . ? O1 La O3 68.19(13) . . ? O2 La O3 66.39(12) . . ? O1A La O4 65.96(12) . . ? O1B La O4 60.73(13) . . ? O1 La O4 67.27(14) . . ? O2 La O4 127.01(14) . . ? O3 La O4 126.07(14) . . ? O1A La N4B 158.42(12) . . ? O1B La N4B 57.79(12) . . ? O1 La N4B 124.86(13) . . ? O2 La N4B 64.80(12) . . ? O3 La N4B 121.85(12) . . ? O4 La N4B 108.05(13) . . ? O1A La N4A 57.95(11) . . ? O1B La N4A 163.01(13) . . ? O1 La N4A 118.68(13) . . ? O2 La N4A 114.99(13) . . ? O3 La N4A 64.14(12) . . ? O4 La N4A 115.62(13) . . ? N4B La N4A 112.37(12) . . ? O1A La N7A 114.71(11) . . ? O1B La N7A 115.14(11) . . ? O1 La N7A 147.86(13) . . ? O2 La N7A 78.68(13) . . ? O3 La N7A 83.95(12) . . ? O4 La N7A 144.87(13) . . ? N4B La N7A 57.35(11) . . ? N4A La N7A 57.01(11) . . ? O1A La Cl1 85.15(9) . . ? O1B La Cl1 89.24(10) . . ? O1 La Cl1 138.96(11) . . ? O2 La Cl1 137.56(10) . . ? O3 La Cl1 138.31(9) . . ? O4 La Cl1 72.13(10) . . ? N4B La Cl1 73.37(9) . . ? N4A La Cl1 74.17(9) . . ? N7A La Cl1 72.96(9) . . ? La O1 H11 101(5) . . ? La O1 H12 115(5) . . ? H11 O1 H12 122(4) . . ? La O2 H21 125(4) . . ? La O2 H22 111(4) . . ? H21 O2 H22 121(4) . . ? La O3 H31 126(4) . . ? La O3 H32 114(4) . . ? H31 O3 H32 120(4) . . ? La O4 H41 136(4) . . ? La O4 H42 92(4) . . ? H41 O4 H42 121(4) . . ? C2A O1A La 129.2(3) . . ? O1A C2A N3A 119.8(4) . . ? O1A C2A C21A 121.6(4) . . ? N3A C2A C21A 118.6(4) . . ? C22A C21A C26A 119.1(5) . . ? C22A C21A C2A 124.0(5) . . ? C26A C21A C2A 116.9(5) . . ? C21A C22A C23A 119.9(5) . . ? C21A C22A H22A 120.1 . . ? C23A C22A H22A 120.1 . . ? C24A C23A C22A 120.3(5) . . ? C24A C23A H23A 119.8 . . ? C22A C23A H23A 119.8 . . ? C23A C24A C25A 120.2(5) . . ? C23A C24A H24A 119.9 . . ? C25A C24A H24A 119.9 . . ? C26A C25A C24A 120.1(6) . . ? C26A C25A H25A 119.9 . . ? C24A C25A H25A 119.9 . . ? C25A C26A C21A 120.3(6) . . ? C25A C26A H26A 119.9 . . ? C21A C26A H26A 119.9 . . ? C2A N3A N4A 116.3(4) . . ? C2A N3A H3A 123(5) . . ? N4A N3A H3A 119(5) . . ? C5A N4A N3A 118.1(4) . . ? C5A N4A La 124.7(3) . . ? N3A N4A La 116.5(3) . . ? N4A C5A C6A 118.2(4) . . ? N4A C5A H5A 120.9 . . ? C6A C5A H5A 120.9 . . ? N7A C6A C8A 122.8(4) . . ? N7A C6A C5A 116.5(4) . . ? C8A C6A C5A 120.5(4) . . ? C6B N7A C6A 117.0(4) . . ? C6B N7A La 121.6(3) . . ? C6A N7A La 121.4(3) . . ? C9A C8A C6A 119.3(5) . . ? C9A C8A H8A 120.4 . . ? C6A C8A H8A 120.4 . . ? C8B C9A C8A 119.0(5) . . ? C8B C9A H9A 120.5 . . ? C8A C9A H9A 120.5 . . ? C9A C8B C6B 119.1(5) . . ? C9A C8B H8B 120.4 . . ? C6B C8B H8B 120.4 . . ? N7A C6B C8B 122.6(5) . . ? N7A C6B C5B 116.8(4) . . ? C8B C6B C5B 120.5(5) . . ? N4B C5B C6B 118.4(4) . . ? N4B C5B H5B 120.8 . . ? C6B C5B H5B 120.8 . . ? C5B N4B N3B 118.0(4) . . ? C5B N4B La 125.2(3) . . ? N3B N4B La 116.7(3) . . ? C2B N3B N4B 116.3(4) . . ? C2B N3B H3B 125(5) . . ? N4B N3B H3B 118(5) . . ? O1B C2B N3B 120.2(5) . . ? O1B C2B C21B 121.1(5) . . ? N3B C2B C21B 118.7(4) . . ? C22B C21B C26B 118.7(5) . . ? C22B C21B C2B 123.8(5) . . ? C26B C21B C2B 117.5(4) . . ? C23B C22B C21B 120.0(5) . . ? C23B C22B H22B 120.0 . . ? C21B C22B H22B 120.0 . . ? C24B C23B C22B 120.8(6) . . ? C24B C23B H23B 119.6 . . ? C22B C23B H23B 119.6 . . ? C23B C24B C25B 119.9(5) . . ? C23B C24B H24B 120.1 . . ? C25B C24B H24B 120.1 . . ? C24B C25B C26B 120.4(6) . . ? C24B C25B H25B 119.8 . . ? C26B C25B H25B 119.8 . . ? C25B C26B C21B 120.3(5) . . ? C25B C26B H26B 119.8 . . ? C21B C26B H26B 119.8 . . ? C2B O1B La 128.2(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 O1B La O1A C2A 160.2(4) . . . . ? O1 La O1A C2A -140.8(5) . . . . ? O2 La O1A C2A -93.7(5) . . . . ? O3 La O1A C2A -69.2(4) . . . . ? O4 La O1A C2A 147.2(5) . . . . ? N4B La O1A C2A 69.0(6) . . . . ? N4A La O1A C2A 0.2(4) . . . . ? N7A La O1A C2A 5.9(5) . . . . ? Cl1 La O1A C2A 74.6(4) . . . . ? La O1A C2A N3A 2.6(7) . . . . ? La O1A C2A C21A -179.1(3) . . . . ? O1A C2A C21A C22A 179.3(5) . . . . ? N3A C2A C21A C22A -2.3(8) . . . . ? O1A C2A C21A C26A -2.2(8) . . . . ? N3A C2A C21A C26A 176.2(5) . . . . ? C26A C21A C22A C23A -1.1(9) . . . . ? C2A C21A C22A C23A 177.3(5) . . . . ? C21A C22A C23A C24A -0.3(10) . . . . ? C22A C23A C24A C25A 2.2(10) . . . . ? C23A C24A C25A C26A -2.5(11) . . . . ? C24A C25A C26A C21A 1.1(11) . . . . ? C22A C21A C26A C25A 0.8(10) . . . . ? C2A C21A C26A C25A -177.8(6) . . . . ? O1A C2A N3A N4A -5.3(7) . . . . ? C21A C2A N3A N4A 176.3(4) . . . . ? C2A N3A N4A C5A 176.1(5) . . . . ? C2A N3A N4A La 5.3(5) . . . . ? O1A La N4A C5A -173.0(4) . . . . ? O1B La N4A C5A 80.0(6) . . . . ? O1 La N4A C5A -129.6(4) . . . . ? O2 La N4A C5A -42.8(4) . . . . ? O3 La N4A C5A -87.0(4) . . . . ? O4 La N4A C5A 153.4(4) . . . . ? N4B La N4A C5A 28.8(4) . . . . ? N7A La N4A C5A 13.1(4) . . . . ? Cl1 La N4A C5A 92.8(4) . . . . ? O1A La N4A N3A -2.9(3) . . . . ? O1B La N4A N3A -109.8(5) . . . . ? O1 La N4A N3A 40.5(4) . . . . ? O2 La N4A N3A 127.3(3) . . . . ? O3 La N4A N3A 83.1(3) . . . . ? O4 La N4A N3A -36.4(4) . . . . ? N4B La N4A N3A -161.1(3) . . . . ? N7A La N4A N3A -176.8(4) . . . . ? Cl1 La N4A N3A -97.1(3) . . . . ? N3A N4A C5A C6A 176.6(4) . . . . ? La N4A C5A C6A -13.5(6) . . . . ? N4A C5A C6A N7A 1.1(7) . . . . ? N4A C5A C6A C8A -173.4(5) . . . . ? C8A C6A N7A C6B 4.1(7) . . . . ? C5A C6A N7A C6B -170.3(4) . . . . ? C8A C6A N7A La -174.5(4) . . . . ? C5A C6A N7A La 11.1(6) . . . . ? O1A La N7A C6B 164.0(4) . . . . ? O1B La N7A C6B 7.0(4) . . . . ? O1 La N7A C6B -97.9(4) . . . . ? O2 La N7A C6B -60.2(4) . . . . ? O3 La N7A C6B -127.3(4) . . . . ? O4 La N7A C6B 81.2(4) . . . . ? N4B La N7A C6B 7.0(3) . . . . ? N4A La N7A C6B 169.7(4) . . . . ? Cl1 La N7A C6B 87.8(4) . . . . ? O1A La N7A C6A -17.4(4) . . . . ? O1B La N7A C6A -174.4(3) . . . . ? O1 La N7A C6A 80.7(4) . . . . ? O2 La N7A C6A 118.3(4) . . . . ? O3 La N7A C6A 51.3(4) . . . . ? O4 La N7A C6A -100.2(4) . . . . ? N4B La N7A C6A -174.5(4) . . . . ? N4A La N7A C6A -11.7(3) . . . . ? Cl1 La N7A C6A -93.6(3) . . . . ? N7A C6A C8A C9A -2.6(8) . . . . ? C5A C6A C8A C9A 171.6(5) . . . . ? C6A C8A C9A C8B -1.0(8) . . . . ? C8A C9A C8B C6B 2.8(8) . . . . ? C6A N7A C6B C8B -2.2(7) . . . . ? La N7A C6B C8B 176.4(4) . . . . ? C6A N7A C6B C5B 173.4(4) . . . . ? La N7A C6B C5B -8.0(6) . . . . ? C9A C8B C6B N7A -1.2(9) . . . . ? C9A C8B C6B C5B -176.6(5) . . . . ? N7A C6B C5B N4B 2.3(8) . . . . ? C8B C6B C5B N4B 178.0(5) . . . . ? C6B C5B N4B N3B -176.3(5) . . . . ? C6B C5B N4B La 4.8(7) . . . . ? O1A La N4B C5B -80.3(5) . . . . ? O1B La N4B C5B 174.0(5) . . . . ? O1 La N4B C5B 135.2(4) . . . . ? O2 La N4B C5B 86.5(4) . . . . ? O3 La N4B C5B 50.9(5) . . . . ? O4 La N4B C5B -150.4(4) . . . . ? N4A La N4B C5B -21.6(5) . . . . ? N7A La N4B C5B -6.0(4) . . . . ? Cl1 La N4B C5B -86.1(4) . . . . ? O1A La N4B N3B 100.8(4) . . . . ? O1B La N4B N3B -4.9(3) . . . . ? O1 La N4B N3B -43.7(4) . . . . ? O2 La N4B N3B -92.4(3) . . . . ? O3 La N4B N3B -128.0(3) . . . . ? O4 La N4B N3B 30.7(4) . . . . ? N4A La N4B N3B 159.5(3) . . . . ? N7A La N4B N3B 175.1(4) . . . . ? Cl1 La N4B N3B 95.0(3) . . . . ? C5B N4B N3B C2B -176.4(5) . . . . ? La N4B N3B C2B 2.6(6) . . . . ? N4B N3B C2B O1B 4.5(7) . . . . ? N4B N3B C2B C21B -173.6(4) . . . . ? O1B C2B C21B C22B -178.3(5) . . . . ? N3B C2B C21B C22B -0.2(8) . . . . ? O1B C2B C21B C26B 0.5(8) . . . . ? N3B C2B C21B C26B 178.6(5) . . . . ? C26B C21B C22B C23B 1.6(9) . . . . ? C2B C21B C22B C23B -179.6(6) . . . . ? C21B C22B C23B C24B -1.0(10) . . . . ? C22B C23B C24B C25B -0.3(10) . . . . ? C23B C24B C25B C26B 1.0(9) . . . . ? C24B C25B C26B C21B -0.3(8) . . . . ? C22B C21B C26B C25B -1.0(8) . . . . ? C2B C21B C26B C25B -179.9(5) . . . . ? N3B C2B O1B La -11.0(8) . . . . ? C21B C2B O1B La 167.1(3) . . . . ? O1A La O1B C2B -145.8(4) . . . . ? O1 La O1B C2B 156.5(5) . . . . ? O2 La O1B C2B 77.9(5) . . . . ? O3 La O1B C2B 114.1(5) . . . . ? O4 La O1B C2B -132.2(5) . . . . ? N4B La O1B C2B 8.4(4) . . . . ? N4A La O1B C2B -50.1(7) . . . . ? N7A La O1B C2B 8.4(5) . . . . ? Cl1 La O1B C2B -62.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.93 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 4.483 _refine_diff_density_min -1.428 _refine_diff_density_rms 0.158