# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Michael Guy Gardiner' _publ_contact_author_address ; School of Chemistry University of Tasmania Private Bag 75 Hobart TAS 7001 AUSTRALIA ; _publ_contact_author_email MICHAEL.GARDINER@UTAS.EDU.AU _publ_section_title ;Sm(II) Reduction Chemistry of Heteroalkynes: Stable Adducts, Reductive Coupling, Reductive C-C/C-N Bond Cleavage and Secondary Trapping of the tert-Butyl Radical with Bulky Nitriles, Phosphaalkynes and Isonitriles ; loop_ _publ_author_name 'Michael Guy Gardiner' 'Adam N. James' 'Cameron Jones' 'Christian Schulten' # Attachment 'compound_2.cif' data_d:\as4g5x _database_code_depnum_ccdc_archive 'CCDC 765856' #TrackingRef 'compound_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C117 H162 N15 Sm3), (C6 H6)' _chemical_formula_sum 'C123 H168 N15 Sm3' _chemical_formula_weight 2307.77 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' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M 'R -3' _symmetry_space_group_name_Hall '-R 3' _symmetry_Int_Tables_number 148 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 27.606(4) _cell_length_b 27.606(4) _cell_length_c 12.420(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 8197(2) _cell_formula_units_Z 3 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 20193 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 24.23 _exptl_crystal_description Prism _exptl_crystal_colour Orange _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3591 _exptl_absorpt_coefficient_mu 1.647 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.75277 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Synchrotron BM' _diffrn_radiation_monochromator Si<111> _diffrn_measurement_device_type '3-BM1 Australian Synchrotron' _diffrn_measurement_method Rotation _diffrn_detector_area_resol_mean 'ADSC Q210' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30441 _diffrn_reflns_av_R_equivalents 0.0830 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 24.23 _reflns_number_total 2899 _reflns_number_gt 2465 _reflns_threshold_expression >2sigma(I) _computing_data_collection BLU-ICE _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 1998)' ; _computing_publication_material 'WinGX (Farrugia, 1999)' _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. The structure was severely disordered on crystallographic -3 sites resulting in a 50:50% occupancy of two orientations. This resulted in partial occupancies of the Sm centre, cyanide ligand and the macrocycle, but full occupancy of the benzene solvent molecule. A number of overlapping macrocycle C/N atoms were included in the refinement model, with the majority able to be separately located. The accuracy of the structure is clearly limited by this issue, that is particularly clear in the nonplanarity of the anionic pyrrolide units where only partial resolution of individual components was possible. The C/N centres of the cyanide ligand were also disordered by necessity of the space group, which also likely features as linkage isomerism in the trimeric species. All hydrogen atoms were placed in calculated positions with extensive use of EXYZ/EADP/part cards. Clearly many of the molecular geometry irregularities flagged in the cif check are either irrelevant (between superimposed disordered components) or relate to the inability to separately locate some near coincident atom positions in the refinement 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^)+(0.1150P)^2^+139.0356P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2899 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.1977 _refine_ls_wR_factor_gt 0.1879 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.008 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sm1 Sm 0.14973(2) 0.08822(2) -0.00397(6) 0.0275(3) Uani 0.50 1 d P . . N1 N 0.2118(3) 0.1503(4) 0.1699(8) 0.081(3) Uani 0.50 1 d P . 2 C30 C 0.2118(3) 0.1503(4) 0.1699(8) 0.081(3) Uani 0.50 1 d P . 1 H30A H 0.1942 0.1110 0.1917 0.121 Uiso 0.50 1 calc PR . 1 H30B H 0.2421 0.1733 0.2199 0.121 Uiso 0.50 1 calc PR . 1 H30C H 0.2269 0.1546 0.0969 0.121 Uiso 0.50 1 calc PR . 1 N2 N 0.2055(4) 0.0410(5) 0.0424(9) 0.030(2) Uani 0.50 1 d P . 2 N3 N 0.2185(4) 0.1053(4) -0.1817(10) 0.031(2) Uani 0.50 1 d P . 1 N4 N 0.1975(4) 0.1921(4) -0.0473(9) 0.031(2) Uani 0.50 1 d P . 1 N5 N 0.0306(4) -0.0576(4) -0.0126(12) 0.038(3) Uani 0.25 1 d P . . N6 N 0.0688(5) -0.0137(6) -0.0005(11) 0.042(3) Uani 0.25 1 d P . . C41 C 0.0306(4) -0.0576(4) -0.0126(12) 0.038(3) Uani 0.25 1 d P . . C42 C 0.0688(5) -0.0137(6) -0.0005(11) 0.042(3) Uani 0.25 1 d P . . C1 C 0.2720(3) 0.1755(4) 0.1449(7) 0.0044(17) Uiso 0.50 1 d P . 2 H1A H 0.2809 0.1990 0.0805 0.007 Uiso 0.50 1 calc PR . 2 H1B H 0.2808 0.1457 0.1318 0.007 Uiso 0.50 1 calc PR . 2 H1C H 0.2942 0.1984 0.2058 0.007 Uiso 0.50 1 calc PR . 2 C2 C 0.1763(6) 0.1655(5) 0.1714(12) 0.102(4) Uani 0.50 1 d P . 2 C29 C 0.1763(6) 0.1655(5) 0.1714(12) 0.102(4) Uani 0.50 1 d P . 1 H29A H 0.1607 0.1606 0.2450 0.122 Uiso 0.50 1 calc PR . 1 H29B H 0.1453 0.1417 0.1220 0.122 Uiso 0.50 1 calc PR . 1 C3 C 0.1213(6) 0.1217(6) 0.1999(12) 0.030(3) Uani 0.50 1 d P . 2 H3 H 0.0885 0.1247 0.2015 0.036 Uiso 0.50 1 calc PR . 2 C4 C 0.1243(6) 0.0739(6) 0.2249(10) 0.033(3) Uani 0.50 1 d P . 2 H4 H 0.0936 0.0384 0.2438 0.040 Uiso 0.50 1 calc PR . 2 C5 C 0.1799(5) 0.0871(5) 0.2175(11) 0.028(3) Uani 0.50 1 d P . 2 C6 C 0.2059(7) 0.0525(7) 0.2424(16) 0.034(4) Uani 0.50 1 d P . 2 C7 C 0.2503(3) 0.0800(3) 0.3316(6) 0.0413(17) Uani 0.50 1 d P . 2 H7A H 0.2838 0.1127 0.3008 0.050 Uiso 0.50 1 calc PR . 2 H7B H 0.2616 0.0529 0.3559 0.050 Uiso 0.50 1 calc PR . 2 C7A C 0.2503(3) 0.0800(3) 0.3316(6) 0.0413(17) Uani 0.50 1 d P A 1 H7A1 H 0.2527 0.1165 0.3368 0.062 Uiso 0.50 1 calc PR A 1 H7A2 H 0.2785 0.0823 0.2806 0.062 Uiso 0.50 1 calc PR A 1 H7A3 H 0.2571 0.0691 0.4026 0.062 Uiso 0.50 1 calc PR A 1 C8 C 0.2305(7) 0.0994(6) 0.4301(13) 0.045(4) Uani 0.50 1 d P . 2 H8A H 0.2138 0.1216 0.4059 0.067 Uiso 0.50 1 calc PR . 2 H8B H 0.2625 0.1223 0.4770 0.067 Uiso 0.50 1 calc PR . 2 H8C H 0.2026 0.0667 0.4701 0.067 Uiso 0.50 1 calc PR . 2 C9 C 0.1584(7) -0.0068(6) 0.2863(13) 0.039(3) Uani 0.50 1 d P . 2 H9A H 0.1316 -0.0283 0.2283 0.047 Uiso 0.50 1 calc PR . 2 H9B H 0.1377 -0.0020 0.3464 0.047 Uiso 0.50 1 calc PR . 2 C10 C 0.2290(5) 0.0427(5) 0.1417(11) 0.033(3) Uani 0.50 1 d P . 2 C11 C 0.2715(3) 0.0182(5) 0.1288(7) 0.071(3) Uani 0.50 1 d P . 2 H11 H 0.2876 0.0063 0.1829 0.085 Uiso 0.50 1 calc PR . 2 C11A C 0.2715(3) 0.0182(5) 0.1288(7) 0.071(3) Uani 0.50 1 d P . 1 H11A H 0.2999 0.0325 0.1824 0.085 Uiso 0.50 1 calc PR . 1 C12 C 0.2779(3) 0.0192(3) 0.0184(7) 0.0429(18) Uani 1 1 d . . . H12 H 0.3086 0.0200 -0.0179 0.051 Uiso 1 1 calc R . 1 C13 C 0.2334(3) 0.0191(3) -0.0310(6) 0.0422(17) Uani 1 1 d . . . C14 C 0.2183(3) 0.0201(4) -0.1424(7) 0.052(2) Uani 1 1 d . . . C15 C 0.2627(3) 0.0236(3) -0.2228(6) 0.0357(15) Uani 1 1 d . . . H15A H 0.2990 0.0570 -0.2049 0.043 Uiso 1 1 calc R . . H15B H 0.2670 -0.0096 -0.2123 0.043 Uiso 1 1 calc R . . C16 C 0.2506(5) 0.0268(7) -0.3403(8) 0.089(4) Uani 1 1 d . . . H16A H 0.2169 -0.0079 -0.3615 0.133 Uiso 1 1 calc R . . H16B H 0.2823 0.0318 -0.3839 0.133 Uiso 1 1 calc R . . H16C H 0.2446 0.0585 -0.3517 0.133 Uiso 1 1 calc R . . C17 C 0.2847(5) 0.1378(3) -0.1418(10) 0.082(4) Uani 0.50 1 d P . 1 H17A H 0.2961 0.1762 -0.1210 0.124 Uiso 0.50 1 calc PR . 1 H17B H 0.3085 0.1382 -0.2009 0.124 Uiso 0.50 1 calc PR . 1 H17C H 0.2887 0.1180 -0.0799 0.124 Uiso 0.50 1 calc PR . 1 C18 C 0.1870(5) 0.0467(4) -0.1769(11) 0.027(3) Uani 0.50 1 d P . 1 C19 C 0.1338(6) 0.0313(7) -0.2088(13) 0.035(4) Uani 0.50 1 d P . 1 H19 H 0.1035 -0.0061 -0.2118 0.043 Uiso 0.50 1 calc PR . 1 C20 C 0.1310(5) 0.0792(5) -0.2364(12) 0.033(3) Uani 0.50 1 d P . 1 H20 H 0.0986 0.0798 -0.2600 0.040 Uiso 0.50 1 calc PR . 1 C21 C 0.1848(5) 0.1263(6) -0.2227(11) 0.034(3) Uani 0.50 1 d P . 1 C22 C 0.2054(6) 0.1855(5) -0.2457(12) 0.034(3) Uani 0.50 1 d P . 1 C23 C 0.2393(8) 0.1955(7) -0.3331(9) 0.122(6) Uani 0.50 1 d P . 1 H23A H 0.2744 0.2012 -0.2999 0.147 Uiso 0.50 1 calc PR . 1 H23B H 0.2477 0.2333 -0.3561 0.147 Uiso 0.50 1 calc PR . 1 C23A C 0.2393(8) 0.1955(7) -0.3331(9) 0.122(6) Uani 0.50 1 d P . 2 H23C H 0.2621 0.2263 -0.2837 0.183 Uiso 0.50 1 calc PR . 2 H23D H 0.2413 0.2105 -0.4055 0.183 Uiso 0.50 1 calc PR . 2 H23E H 0.2534 0.1693 -0.3349 0.183 Uiso 0.50 1 calc PR . 2 C24 C 0.2381(7) 0.1699(7) -0.4310(12) 0.051(4) Uani 0.50 1 d P . . H24A H 0.2734 0.1927 -0.4695 0.076 Uiso 0.50 1 calc PR . 1 H24B H 0.2069 0.1661 -0.4749 0.076 Uiso 0.50 1 calc PR . 1 H24C H 0.2332 0.1327 -0.4172 0.076 Uiso 0.50 1 calc PR . 1 C25 C 0.1908(8) 0.0355(8) 0.2914(17) 0.039(4) Uani 0.50 1 d P A 1 H25A H 0.1792 0.0527 0.2345 0.046 Uiso 0.50 1 calc PR A 1 H25B H 0.1642 0.0257 0.3520 0.046 Uiso 0.50 1 calc PR A 1 C26 C 0.2246(5) 0.2173(5) -0.1425(12) 0.032(3) Uani 0.50 1 d P . 1 C27 C 0.1439(7) 0.2321(6) 0.1368(15) 0.044(4) Uani 0.50 1 d P . 3 H27A H 0.1239 0.2148 0.0689 0.052 Uiso 0.50 1 calc PR . 3 H27B H 0.1182 0.2097 0.1956 0.052 Uiso 0.50 1 calc PR . 3 C28 C 0.2847(5) 0.1378(3) -0.1418(10) 0.082(4) Uani 0.50 1 d P B 3 H28A H 0.3138 0.1283 -0.1572 0.124 Uiso 0.50 1 calc PR B 3 H28B H 0.2926 0.1574 -0.0726 0.124 Uiso 0.50 1 calc PR B 3 H28C H 0.2842 0.1620 -0.1989 0.124 Uiso 0.50 1 calc PR B 3 C40 C 0.0569(4) 0.0332(6) 0.5000(9) 0.080(3) Uani 1 1 d . . . H40 H 0.0965 0.0563 0.4998 0.096 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 Sm1 0.0123(4) 0.0147(4) 0.0549(5) 0.0029(2) 0.0004(2) 0.0062(3) N1 0.013(3) 0.108(8) 0.119(8) -0.064(6) -0.013(4) 0.028(4) C30 0.013(3) 0.108(8) 0.119(8) -0.064(6) -0.013(4) 0.028(4) N2 0.025(5) 0.032(6) 0.039(6) 0.001(5) 0.001(4) 0.019(5) N3 0.014(5) 0.020(6) 0.051(7) 0.001(5) 0.002(5) 0.003(5) N4 0.013(5) 0.031(6) 0.047(7) 0.002(5) 0.000(4) 0.011(5) N5 0.008(6) 0.012(6) 0.083(10) -0.002(5) -0.008(5) -0.002(6) N6 0.030(8) 0.044(10) 0.062(9) 0.008(6) 0.001(6) 0.027(8) C41 0.008(6) 0.012(6) 0.083(10) -0.002(5) -0.008(5) -0.002(6) C42 0.030(8) 0.044(10) 0.062(9) 0.008(6) 0.001(6) 0.027(8) C2 0.078(8) 0.065(8) 0.144(12) 0.002(7) -0.002(8) 0.022(7) C29 0.078(8) 0.065(8) 0.144(12) 0.002(7) -0.002(8) 0.022(7) C3 0.022(8) 0.018(7) 0.047(9) 0.006(6) 0.004(6) 0.008(6) C4 0.028(7) 0.030(7) 0.038(8) 0.006(5) 0.011(5) 0.012(6) C5 0.028(6) 0.011(5) 0.043(7) 0.008(5) 0.000(5) 0.008(5) C6 0.025(8) 0.017(8) 0.056(12) 0.010(7) 0.001(7) 0.006(7) C7 0.039(4) 0.026(4) 0.055(5) -0.001(3) -0.007(3) 0.014(3) C7A 0.039(4) 0.026(4) 0.055(5) -0.001(3) -0.007(3) 0.014(3) C8 0.049(9) 0.042(8) 0.053(9) 0.000(7) 0.004(7) 0.030(7) C9 0.038(8) 0.011(7) 0.061(10) 0.015(6) 0.007(7) 0.007(7) C10 0.031(7) 0.024(7) 0.050(8) 0.002(6) 0.002(6) 0.018(6) C11 0.025(4) 0.098(8) 0.054(6) 0.004(5) -0.006(3) 0.004(4) C11A 0.025(4) 0.098(8) 0.054(6) 0.004(5) -0.006(3) 0.004(4) C12 0.037(4) 0.032(4) 0.067(5) -0.003(3) -0.005(3) 0.022(3) C13 0.023(3) 0.041(4) 0.049(4) -0.002(3) 0.003(3) 0.006(3) C14 0.044(5) 0.079(6) 0.056(5) 0.009(4) 0.005(4) 0.048(5) C15 0.026(3) 0.028(3) 0.056(4) 0.000(3) -0.002(3) 0.016(3) C16 0.070(7) 0.164(12) 0.063(6) 0.002(7) 0.004(5) 0.082(8) C17 0.080(7) 0.018(4) 0.111(8) -0.010(4) 0.043(6) -0.005(4) C18 0.015(6) 0.006(5) 0.053(8) -0.004(5) -0.006(5) -0.001(5) C19 0.025(8) 0.018(8) 0.051(9) -0.006(7) 0.002(6) 0.001(7) C20 0.024(6) 0.017(6) 0.062(9) -0.002(6) -0.007(6) 0.013(5) C21 0.018(6) 0.033(7) 0.053(8) 0.006(6) 0.009(6) 0.015(6) C22 0.028(7) 0.025(7) 0.053(9) -0.001(6) -0.011(6) 0.015(6) C23 0.234(18) 0.200(16) 0.061(7) 0.024(8) 0.026(8) 0.205(16) C23A 0.234(18) 0.200(16) 0.061(7) 0.024(8) 0.026(8) 0.205(16) C24 0.052(9) 0.048(9) 0.044(9) 0.003(7) 0.007(7) 0.020(8) C25 0.040(11) 0.030(13) 0.054(13) 0.001(8) -0.004(8) 0.023(11) C26 0.021(6) 0.017(6) 0.064(9) 0.009(6) 0.004(6) 0.014(5) C27 0.035(9) 0.037(9) 0.066(11) 0.010(8) 0.015(8) 0.023(7) C28 0.080(7) 0.018(4) 0.111(8) -0.010(4) 0.043(6) -0.005(4) C40 0.056(6) 0.086(8) 0.078(7) -0.004(5) -0.009(5) 0.020(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 Sm1 C42 1.656(12) 12 ? Sm1 N6 1.656(12) 12 ? Sm1 C41 1.661(11) 12 ? Sm1 N5 1.661(11) 12 ? Sm1 N2 2.530(10) . ? Sm1 N4 2.544(11) . ? Sm1 C41 2.545(10) 2 ? Sm1 N5 2.545(10) 2 ? Sm1 N6 2.574(14) . ? Sm1 N1 2.756(8) . ? Sm1 N3 2.793(11) . ? N1 C2 1.242(16) . ? N1 C1 1.479(10) . ? N1 C5 1.622(16) . ? N2 C10 1.385(17) . ? N2 C13 1.503(13) . ? N3 C18 1.405(15) . ? N3 C21 1.413(18) . ? N3 C17 1.659(16) . ? N4 C26 1.386(17) . ? N4 C13 1.390(13) 12 ? N5 C42 1.074(17) 11 ? N5 N6 1.074(17) 11 ? N5 N6 1.150(17) . ? N5 Sm1 1.661(11) 11 ? N5 Sm1 2.546(10) 3 ? N6 C41 1.074(17) 12 ? N6 N5 1.074(17) 12 ? N6 Sm1 1.656(12) 11 ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C14 1.318(15) 12 ? C2 C3 1.435(19) . ? C3 C4 1.40(2) . ? C3 H3 0.9500 . ? C4 C5 1.392(19) . ? C4 H4 0.9500 . ? C5 C6 1.49(2) . ? C6 C10 1.49(2) . ? C6 C7 1.541(19) . ? C6 C9 1.597(18) . ? C7 C8 1.541(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C23A 1.86(2) 11 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.628(16) . ? C11 C12 1.381(12) . ? C11 H11 0.9500 . ? C12 C13 1.372(10) . ? C12 H12 0.9500 . ? C13 N4 1.390(13) 11 ? C13 C14 1.450(11) . ? C14 C29 1.318(15) 11 ? C14 C2 1.318(15) 11 ? C14 C18 1.449(14) . ? C14 C15 1.547(10) . ? C14 C27 1.723(17) 11 ? C15 C16 1.510(12) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.37(2) . ? C18 C29 1.391(18) 11 ? C19 C20 1.41(2) . ? C19 C29 1.83(2) 11 ? C19 H19 0.9500 . ? C20 C21 1.411(18) . ? C20 H20 0.9500 . ? C21 C22 1.467(18) . ? C22 C23 1.369(19) . ? C22 C26 1.49(2) . ? C22 C25 1.57(2) 12 ? C23 C24 1.400(19) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C22 1.57(2) 11 ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 C11A 1.308(15) 12 ? C27 C28 1.414(17) 12 ? C27 C14 1.723(17) 12 ? C27 Sm1 2.810(17) 12 ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C40 C40 1.367(10) 11_556 ? C40 C40 1.367(10) 12_556 ? C40 H40 0.9500 . ? 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 C42 Sm1 N6 0.0(14) 12 12 ? C42 Sm1 C41 40.6(6) 12 12 ? N6 Sm1 C41 40.6(6) 12 12 ? C42 Sm1 N5 40.6(6) 12 12 ? N6 Sm1 N5 40.6(6) 12 12 ? C41 Sm1 N5 0.0(13) 12 12 ? C42 Sm1 N2 134.2(5) 12 . ? N6 Sm1 N2 134.2(5) 12 . ? C41 Sm1 N2 94.2(4) 12 . ? N5 Sm1 N2 94.2(4) 12 . ? C42 Sm1 N4 103.8(5) 12 . ? N6 Sm1 N4 103.8(5) 12 . ? C41 Sm1 N4 144.2(4) 12 . ? N5 Sm1 N4 144.2(4) 12 . ? N2 Sm1 N4 121.5(3) . . ? C42 Sm1 C41 16.8(5) 12 2 ? N6 Sm1 C41 16.8(5) 12 2 ? C41 Sm1 C41 57.4(5) 12 2 ? N5 Sm1 C41 57.4(5) 12 2 ? N2 Sm1 C41 150.9(4) . 2 ? N4 Sm1 C41 86.9(3) . 2 ? C42 Sm1 N5 16.8(5) 12 2 ? N6 Sm1 N5 16.8(5) 12 2 ? C41 Sm1 N5 57.4(5) 12 2 ? N5 Sm1 N5 57.4(5) 12 2 ? N2 Sm1 N5 150.9(4) . 2 ? N4 Sm1 N5 86.9(3) . 2 ? C41 Sm1 N5 0.0(9) 2 2 ? C42 Sm1 N6 54.9(6) 12 . ? N6 Sm1 N6 54.9(6) 12 . ? C41 Sm1 N6 15.7(5) 12 . ? N5 Sm1 N6 15.7(5) 12 . ? N2 Sm1 N6 81.5(4) . . ? N4 Sm1 N6 156.0(3) . . ? C41 Sm1 N6 71.3(4) 2 . ? N5 Sm1 N6 71.3(4) 2 . ? C42 Sm1 N1 115.0(5) 12 . ? N6 Sm1 N1 115.0(5) 12 . ? C41 Sm1 N1 121.2(6) 12 . ? N5 Sm1 N1 121.2(6) 12 . ? N2 Sm1 N1 78.1(3) . . ? N4 Sm1 N1 69.8(4) . . ? C41 Sm1 N1 110.1(3) 2 . ? N5 Sm1 N1 110.1(3) 2 . ? N6 Sm1 N1 126.6(4) . . ? C42 Sm1 N3 129.7(5) 12 . ? N6 Sm1 N3 129.7(5) 12 . ? C41 Sm1 N3 122.9(5) 12 . ? N5 Sm1 N3 122.9(5) 12 . ? N2 Sm1 N3 74.3(4) . . ? N4 Sm1 N3 73.6(3) . . ? C41 Sm1 N3 124.1(4) 2 . ? N5 Sm1 N3 124.1(4) 2 . ? N6 Sm1 N3 110.1(4) . . ? N1 Sm1 N3 110.8(3) . . ? C2 N1 C1 137.2(11) . . ? C2 N1 C5 105.2(9) . . ? C1 N1 C5 117.4(8) . . ? C2 N1 Sm1 82.7(8) . . ? C1 N1 Sm1 109.3(5) . . ? C5 N1 Sm1 77.4(5) . . ? C10 N2 C13 103.0(9) . . ? C10 N2 Sm1 125.6(8) . . ? C13 N2 Sm1 129.5(7) . . ? C18 N3 C21 109.4(10) . . ? C18 N3 C17 119.3(11) . . ? C21 N3 C17 131.3(10) . . ? C18 N3 Sm1 78.2(7) . . ? C21 N3 Sm1 79.9(7) . . ? C17 N3 Sm1 109.1(7) . . ? C26 N4 C13 108.0(9) . 12 ? C26 N4 Sm1 126.3(8) . . ? C13 N4 Sm1 123.4(7) 12 . ? C42 N5 N6 0(3) 11 11 ? C42 N5 N6 143.6(16) 11 . ? N6 N5 N6 143.6(16) 11 . ? C42 N5 Sm1 139.5(11) 11 11 ? N6 N5 Sm1 139.5(11) 11 11 ? N6 N5 Sm1 69.4(8) . 11 ? C42 N5 Sm1 26.5(7) 11 3 ? N6 N5 Sm1 26.5(7) 11 3 ? N6 N5 Sm1 168.0(12) . 3 ? Sm1 N5 Sm1 116.1(5) 11 3 ? C41 N6 N5 0.0(19) 12 12 ? C41 N6 N5 152.9(16) 12 . ? N5 N6 N5 152.9(16) 12 . ? C41 N6 Sm1 136.6(11) 12 11 ? N5 N6 Sm1 136.6(11) 12 11 ? N5 N6 Sm1 70.0(9) . 11 ? C41 N6 Sm1 24.8(7) 12 . ? N5 N6 Sm1 24.8(7) 12 . ? N5 N6 Sm1 170.5(12) . . ? Sm1 N6 Sm1 114.9(6) 11 . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C14 111.5(12) . 12 ? N1 C2 C3 113.6(13) . . ? C14 C2 C3 134.8(14) 12 . ? N1 C2 Sm1 71.9(8) . . ? C14 C2 Sm1 114.7(9) 12 . ? C3 C2 Sm1 78.0(8) . . ? C4 C3 C2 108.2(13) . . ? C4 C3 Sm1 75.1(8) . . ? C2 C3 Sm1 73.4(9) . . ? C4 C3 H3 125.9 . . ? C2 C3 H3 125.9 . . ? Sm1 C3 H3 117.5 . . ? C5 C4 C3 108.5(11) . . ? C5 C4 Sm1 74.9(7) . . ? C3 C4 Sm1 77.2(8) . . ? C5 C4 H4 125.8 . . ? C3 C4 H4 125.8 . . ? Sm1 C4 H4 114.3 . . ? C4 C5 C6 130.0(12) . . ? C4 C5 N1 103.9(9) . . ? C6 C5 N1 126.1(11) . . ? C4 C5 Sm1 77.3(8) . . ? C6 C5 Sm1 116.2(10) . . ? N1 C5 Sm1 69.2(5) . . ? C5 C6 C10 109.3(14) . . ? C5 C6 C7 110.8(12) . . ? C10 C6 C7 112.6(12) . . ? C5 C6 C9 108.6(12) . . ? C10 C6 C9 107.8(13) . . ? C7 C6 C9 107.6(13) . . ? C6 C7 C8 114.1(10) . . ? C6 C7 H7A 108.7 . . ? C8 C7 H7A 108.7 . . ? C6 C7 H7B 108.7 . . ? C8 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 C23A 105.9(11) . 11 ? C6 C9 H9A 110.5 . . ? C23A C9 H9A 110.5 11 . ? C6 C9 H9B 110.5 . . ? C23A C9 H9B 110.5 11 . ? H9A C9 H9B 108.7 . . ? N2 C10 C6 121.1(11) . . ? N2 C10 C11 108.8(10) . . ? C6 C10 C11 128.4(11) . . ? C12 C11 C10 101.5(8) . . ? C12 C11 H11 129.2 . . ? C10 C11 H11 129.2 . . ? C13 C12 C11 109.8(7) . . ? C13 C12 H12 125.1 . . ? C11 C12 H12 125.1 . . ? C12 C13 N4 101.8(8) . 11 ? C12 C13 C14 133.9(7) . . ? N4 C13 C14 120.1(7) 11 . ? C12 C13 N2 111.6(7) . . ? N4 C13 N2 46.4(6) 11 . ? C14 C13 N2 111.1(7) . . ? C29 C14 C2 0(2) 11 11 ? C29 C14 C18 60.1(8) 11 . ? C2 C14 C18 60.1(8) 11 . ? C29 C14 C13 119.0(9) 11 . ? C2 C14 C13 119.0(9) 11 . ? C18 C14 C13 122.9(8) . . ? C29 C14 C15 116.7(9) 11 . ? C2 C14 C15 116.7(9) 11 . ? C18 C14 C15 115.5(8) . . ? C13 C14 C15 113.0(6) . . ? C29 C14 C27 106.7(10) 11 11 ? C2 C14 C27 106.7(10) 11 11 ? C18 C14 C27 47.3(8) . 11 ? C13 C14 C27 94.2(8) . 11 ? C15 C14 C27 102.8(8) . 11 ? C16 C15 C14 115.8(6) . . ? C16 C15 H15A 108.3 . . ? C14 C15 H15A 108.3 . . ? C16 C15 H15B 108.3 . . ? C14 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C19 C18 C29 83.1(10) . 11 ? C19 C18 N3 107.1(12) . . ? C29 C18 N3 169.4(12) 11 . ? C19 C18 C14 138.3(11) . . ? C29 C18 C14 55.3(8) 11 . ? N3 C18 C14 114.5(10) . . ? C19 C18 Sm1 78.2(8) . . ? C29 C18 Sm1 112.8(9) 11 . ? N3 C18 Sm1 73.0(7) . . ? C14 C18 Sm1 113.9(8) . . ? C18 C19 C20 109.5(13) . . ? C18 C19 C29 49.0(8) . 11 ? C20 C19 C29 158.2(13) . 11 ? C18 C19 Sm1 74.4(8) . . ? C20 C19 Sm1 76.6(9) . . ? C29 C19 Sm1 97.5(8) 11 . ? C18 C19 H19 125.2 . . ? C20 C19 H19 125.2 . . ? C29 C19 H19 76.3 11 . ? Sm1 C19 H19 115.7 . . ? C19 C20 C21 108.0(12) . . ? C19 C20 Sm1 75.4(9) . . ? C21 C20 Sm1 75.1(8) . . ? C19 C20 H20 126.0 . . ? C21 C20 H20 126.0 . . ? Sm1 C20 H20 115.6 . . ? C20 C21 N3 105.7(11) . . ? C20 C21 C22 130.2(12) . . ? N3 C21 C22 124.0(11) . . ? C20 C21 Sm1 76.8(8) . . ? N3 C21 Sm1 71.5(7) . . ? C22 C21 Sm1 117.3(9) . . ? C23 C22 C21 102.9(12) . . ? C23 C22 C26 123.8(13) . . ? C21 C22 C26 108.3(11) . . ? C23 C22 C25 103.9(13) . 12 ? C21 C22 C25 107.9(12) . 12 ? C26 C22 C25 109.1(13) . 12 ? C22 C23 C24 138.3(18) . . ? C22 C23 H23A 102.5 . . ? C24 C23 H23A 102.5 . . ? C22 C23 H23B 102.5 . . ? C24 C23 H23B 102.5 . . ? H23A C23 H23B 104.9 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C22 C25 H25A 108.4 11 . ? C22 C25 H25B 108.4 11 . ? H25A C25 H25B 107.4 . . ? C11A C26 N4 109.3(12) 12 . ? C11A C26 C22 128.2(12) 12 . ? N4 C26 C22 119.6(11) . . ? C28 C27 C14 127.9(12) 12 12 ? C28 C27 Sm1 117.7(10) 12 12 ? C14 C27 Sm1 106.6(7) 12 12 ? C28 C27 H27A 105.3 12 . ? C14 C27 H27A 105.3 12 . ? Sm1 C27 H27A 23.0 12 . ? C28 C27 H27B 105.3 12 . ? C14 C27 H27B 105.3 12 . ? Sm1 C27 H27B 83.7 12 . ? H27A C27 H27B 106.0 . . ? C40 C40 C40 120.000(10) 11_556 12_556 ? C40 C40 H40 120.0 11_556 . ? C40 C40 H40 120.0 12_556 . ? 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 C42 Sm1 N1 C2 -29.6(10) 12 . . . ? N6 Sm1 N1 C2 -29.6(10) 12 . . . ? C41 Sm1 N1 C2 -75.4(10) 12 . . . ? N5 Sm1 N1 C2 -75.4(10) 12 . . . ? N2 Sm1 N1 C2 -163.1(9) . . . . ? N4 Sm1 N1 C2 66.6(9) . . . . ? C41 Sm1 N1 C2 -12.1(9) 2 . . . ? N5 Sm1 N1 C2 -12.1(9) 2 . . . ? N6 Sm1 N1 C2 -93.3(9) . . . . ? N3 Sm1 N1 C2 129.0(8) . . . . ? C42 Sm1 N1 C1 -167.3(8) 12 . . . ? N6 Sm1 N1 C1 -167.3(8) 12 . . . ? C41 Sm1 N1 C1 146.9(7) 12 . . . ? N5 Sm1 N1 C1 146.9(7) 12 . . . ? N2 Sm1 N1 C1 59.3(7) . . . . ? N4 Sm1 N1 C1 -71.1(7) . . . . ? C41 Sm1 N1 C1 -149.8(7) 2 . . . ? N5 Sm1 N1 C1 -149.8(7) 2 . . . ? N6 Sm1 N1 C1 129.1(7) . . . . ? N3 Sm1 N1 C1 -8.6(8) . . . . ? C42 Sm1 N1 C5 77.8(8) 12 . . . ? N6 Sm1 N1 C5 77.8(8) 12 . . . ? C41 Sm1 N1 C5 32.0(7) 12 . . . ? N5 Sm1 N1 C5 32.0(7) 12 . . . ? N2 Sm1 N1 C5 -55.6(6) . . . . ? N4 Sm1 N1 C5 174.0(6) . . . . ? C41 Sm1 N1 C5 95.3(6) 2 . . . ? N5 Sm1 N1 C5 95.3(6) 2 . . . ? N6 Sm1 N1 C5 14.2(7) . . . . ? N3 Sm1 N1 C5 -123.6(6) . . . . ? C42 Sm1 N2 C10 -90.7(12) 12 . . . ? N6 Sm1 N2 C10 -90.7(12) 12 . . . ? C41 Sm1 N2 C10 -98.3(11) 12 . . . ? N5 Sm1 N2 C10 -98.3(11) 12 . . . ? N4 Sm1 N2 C10 79.7(10) . . . . ? C41 Sm1 N2 C10 -87.3(12) 2 . . . ? N5 Sm1 N2 C10 -87.3(12) 2 . . . ? N6 Sm1 N2 C10 -107.7(10) . . . . ? N1 Sm1 N2 C10 22.7(10) . . . . ? N3 Sm1 N2 C10 138.6(10) . . . . ? C42 Sm1 N2 C13 107.4(10) 12 . . . ? N6 Sm1 N2 C13 107.4(10) 12 . . . ? C41 Sm1 N2 C13 99.7(9) 12 . . . ? N5 Sm1 N2 C13 99.7(9) 12 . . . ? N4 Sm1 N2 C13 -82.3(9) . . . . ? C41 Sm1 N2 C13 110.7(10) 2 . . . ? N5 Sm1 N2 C13 110.7(10) 2 . . . ? N6 Sm1 N2 C13 90.3(9) . . . . ? N1 Sm1 N2 C13 -139.3(9) . . . . ? N3 Sm1 N2 C13 -23.4(8) . . . . ? C42 Sm1 N3 C18 -75.3(10) 12 . . . ? N6 Sm1 N3 C18 -75.3(10) 12 . . . ? C41 Sm1 N3 C18 -24.9(10) 12 . . . ? N5 Sm1 N3 C18 -24.9(10) 12 . . . ? N2 Sm1 N3 C18 59.8(7) . . . . ? N4 Sm1 N3 C18 -169.7(8) . . . . ? C41 Sm1 N3 C18 -95.2(8) 2 . . . ? N5 Sm1 N3 C18 -95.2(8) 2 . . . ? N6 Sm1 N3 C18 -14.8(8) . . . . ? N1 Sm1 N3 C18 130.2(7) . . . . ? C42 Sm1 N3 C21 37.2(10) 12 . . . ? N6 Sm1 N3 C21 37.2(10) 12 . . . ? C41 Sm1 N3 C21 87.6(9) 12 . . . ? N5 Sm1 N3 C21 87.6(9) 12 . . . ? N2 Sm1 N3 C21 172.3(8) . . . . ? N4 Sm1 N3 C21 -57.2(7) . . . . ? C41 Sm1 N3 C21 17.3(8) 2 . . . ? N5 Sm1 N3 C21 17.3(8) 2 . . . ? N6 Sm1 N3 C21 97.7(7) . . . . ? N1 Sm1 N3 C21 -117.3(7) . . . . ? C42 Sm1 N3 C17 167.6(8) 12 . . . ? N6 Sm1 N3 C17 167.6(8) 12 . . . ? C41 Sm1 N3 C17 -142.1(7) 12 . . . ? N5 Sm1 N3 C17 -142.1(7) 12 . . . ? N2 Sm1 N3 C17 -57.3(7) . . . . ? N4 Sm1 N3 C17 73.1(7) . . . . ? C41 Sm1 N3 C17 147.6(6) 2 . . . ? N5 Sm1 N3 C17 147.6(6) 2 . . . ? N6 Sm1 N3 C17 -131.9(7) . . . . ? N1 Sm1 N3 C17 13.0(8) . . . . ? C42 Sm1 N4 C26 -111.4(10) 12 . . . ? N6 Sm1 N4 C26 -111.4(10) 12 . . . ? C41 Sm1 N4 C26 -107.7(12) 12 . . . ? N5 Sm1 N4 C26 -107.7(12) 12 . . . ? N2 Sm1 N4 C26 75.7(10) . . . . ? C41 Sm1 N4 C26 -110.6(10) 2 . . . ? N5 Sm1 N4 C26 -110.6(10) 2 . . . ? N6 Sm1 N4 C26 -86.1(13) . . . . ? N1 Sm1 N4 C26 136.7(10) . . . . ? N3 Sm1 N4 C26 16.4(9) . . . . ? C42 Sm1 N4 C13 88.0(9) 12 . . 12 ? N6 Sm1 N4 C13 88.0(9) 12 . . 12 ? C41 Sm1 N4 C13 91.8(12) 12 . . 12 ? N5 Sm1 N4 C13 91.8(12) 12 . . 12 ? N2 Sm1 N4 C13 -84.9(8) . . . 12 ? C41 Sm1 N4 C13 88.8(8) 2 . . 12 ? N5 Sm1 N4 C13 88.8(8) 2 . . 12 ? N6 Sm1 N4 C13 113.3(11) . . . 12 ? N1 Sm1 N4 C13 -23.9(7) . . . 12 ? N3 Sm1 N4 C13 -144.2(8) . . . 12 ? C42 N5 N6 C41 -21(3) 11 . . 12 ? N6 N5 N6 C41 -21(3) 11 . . 12 ? Sm1 N5 N6 C41 -171(3) 11 . . 12 ? Sm1 N5 N6 C41 -51(7) 3 . . 12 ? C42 N5 N6 N5 -21(3) 11 . . 12 ? N6 N5 N6 N5 -21(3) 11 . . 12 ? Sm1 N5 N6 N5 -171(3) 11 . . 12 ? Sm1 N5 N6 N5 -51(7) 3 . . 12 ? C42 N5 N6 Sm1 149(3) 11 . . 11 ? N6 N5 N6 Sm1 149(3) 11 . . 11 ? Sm1 N5 N6 Sm1 120(5) 3 . . 11 ? C42 N5 N6 Sm1 -88(7) 11 . . . ? N6 N5 N6 Sm1 -88(7) 11 . . . ? Sm1 N5 N6 Sm1 123(7) 11 . . . ? Sm1 N5 N6 Sm1 -118(7) 3 . . . ? C42 Sm1 N6 C41 -21.8(18) 12 . . 12 ? N6 Sm1 N6 C41 -21.8(18) 12 . . 12 ? N5 Sm1 N6 C41 0.0 12 . . 12 ? N2 Sm1 N6 C41 143(2) . . . 12 ? N4 Sm1 N6 C41 -52(2) . . . 12 ? C41 Sm1 N6 C41 -26(2) 2 . . 12 ? N5 Sm1 N6 C41 -26(2) 2 . . 12 ? N1 Sm1 N6 C41 75(2) . . . 12 ? N3 Sm1 N6 C41 -147(2) . . . 12 ? C42 Sm1 N6 N5 -21.8(18) 12 . . 12 ? N6 Sm1 N6 N5 -21.8(18) 12 . . 12 ? C41 Sm1 N6 N5 0.0 12 . . 12 ? N2 Sm1 N6 N5 143(2) . . . 12 ? N4 Sm1 N6 N5 -52(2) . . . 12 ? C41 Sm1 N6 N5 -26(2) 2 . . 12 ? N5 Sm1 N6 N5 -26(2) 2 . . 12 ? N1 Sm1 N6 N5 75(2) . . . 12 ? N3 Sm1 N6 N5 -147(2) . . . 12 ? C42 Sm1 N6 N5 64(6) 12 . . . ? N6 Sm1 N6 N5 64(6) 12 . . . ? C41 Sm1 N6 N5 86(8) 12 . . . ? N5 Sm1 N6 N5 86(8) 12 . . . ? N2 Sm1 N6 N5 -131(7) . . . . ? N4 Sm1 N6 N5 34(7) . . . . ? C41 Sm1 N6 N5 60(7) 2 . . . ? N5 Sm1 N6 N5 60(7) 2 . . . ? N1 Sm1 N6 N5 161(7) . . . . ? N3 Sm1 N6 N5 -61(7) . . . . ? C42 Sm1 N6 Sm1 -176.6(15) 12 . . 11 ? N6 Sm1 N6 Sm1 -176.6(15) 12 . . 11 ? C41 Sm1 N6 Sm1 -155(2) 12 . . 11 ? N5 Sm1 N6 Sm1 -155(2) 12 . . 11 ? N2 Sm1 N6 Sm1 -11.5(7) . . . 11 ? N4 Sm1 N6 Sm1 152.9(7) . . . 11 ? C41 Sm1 N6 Sm1 178.8(9) 2 . . 11 ? N5 Sm1 N6 Sm1 178.8(9) 2 . . 11 ? N1 Sm1 N6 Sm1 -79.6(8) . . . 11 ? N3 Sm1 N6 Sm1 58.4(8) . . . 11 ? C1 N1 C2 C14 0(2) . . . 12 ? C5 N1 C2 C14 175.0(10) . . . 12 ? Sm1 N1 C2 C14 -110.2(11) . . . 12 ? C1 N1 C2 C3 178.2(12) . . . . ? C5 N1 C2 C3 -7.2(16) . . . . ? Sm1 N1 C2 C3 67.6(12) . . . . ? C1 N1 C2 Sm1 110.6(14) . . . . ? C5 N1 C2 Sm1 -74.8(7) . . . . ? C42 Sm1 C2 N1 153.4(9) 12 . . . ? N6 Sm1 C2 N1 153.4(9) 12 . . . ? C41 Sm1 C2 N1 116.7(9) 12 . . . ? N5 Sm1 C2 N1 116.7(9) 12 . . . ? N2 Sm1 C2 N1 17.0(9) . . . . ? N4 Sm1 C2 N1 -102.4(9) . . . . ? C41 Sm1 C2 N1 168.6(9) 2 . . . ? N5 Sm1 C2 N1 168.6(9) 2 . . . ? N6 Sm1 C2 N1 105.0(9) . . . . ? N3 Sm1 C2 N1 -62.4(10) . . . . ? C42 Sm1 C2 C14 -100.7(10) 12 . . 12 ? N6 Sm1 C2 C14 -100.7(10) 12 . . 12 ? C41 Sm1 C2 C14 -137.3(9) 12 . . 12 ? N5 Sm1 C2 C14 -137.3(9) 12 . . 12 ? N2 Sm1 C2 C14 122.9(9) . . . 12 ? N4 Sm1 C2 C14 3.6(8) . . . 12 ? C41 Sm1 C2 C14 -85.5(10) 2 . . 12 ? N5 Sm1 C2 C14 -85.5(10) 2 . . 12 ? N6 Sm1 C2 C14 -149.1(8) . . . 12 ? N1 Sm1 C2 C14 105.9(13) . . . 12 ? N3 Sm1 C2 C14 43.5(11) . . . 12 ? C42 Sm1 C2 C3 33.4(10) 12 . . . ? N6 Sm1 C2 C3 33.4(10) 12 . . . ? C41 Sm1 C2 C3 -3.3(10) 12 . . . ? N5 Sm1 C2 C3 -3.3(10) 12 . . . ? N2 Sm1 C2 C3 -103.0(9) . . . . ? N4 Sm1 C2 C3 137.7(10) . . . . ? C41 Sm1 C2 C3 48.6(9) 2 . . . ? N5 Sm1 C2 C3 48.6(9) 2 . . . ? N6 Sm1 C2 C3 -15.0(10) . . . . ? N1 Sm1 C2 C3 -120.0(13) . . . . ? N3 Sm1 C2 C3 177.6(8) . . . . ? N1 C2 C3 C4 3.7(18) . . . . ? C14 C2 C3 C4 -179.3(16) 12 . . . ? Sm1 C2 C3 C4 67.6(10) . . . . ? N1 C2 C3 Sm1 -64.0(11) . . . . ? C14 C2 C3 Sm1 113.1(18) 12 . . . ? C42 Sm1 C3 C4 101.5(9) 12 . . . ? N6 Sm1 C3 C4 101.5(9) 12 . . . ? C41 Sm1 C3 C4 62.4(9) 12 . . . ? N5 Sm1 C3 C4 62.4(9) 12 . . . ? N2 Sm1 C3 C4 -30.0(9) . . . . ? N4 Sm1 C3 C4 -151.2(8) . . . . ? C41 Sm1 C3 C4 119.6(9) 2 . . . ? N5 Sm1 C3 C4 119.6(9) 2 . . . ? N6 Sm1 C3 C4 52.9(8) . . . . ? N1 Sm1 C3 C4 -83.7(9) . . . . ? N3 Sm1 C3 C4 -119.0(10) . . . . ? C42 Sm1 C3 C2 -143.9(10) 12 . . . ? N6 Sm1 C3 C2 -143.9(10) 12 . . . ? C41 Sm1 C3 C2 177.0(10) 12 . . . ? N5 Sm1 C3 C2 177.0(10) 12 . . . ? N2 Sm1 C3 C2 84.5(9) . . . . ? N4 Sm1 C3 C2 -36.7(9) . . . . ? C41 Sm1 C3 C2 -125.8(10) 2 . . . ? N5 Sm1 C3 C2 -125.8(10) 2 . . . ? N6 Sm1 C3 C2 167.5(9) . . . . ? N1 Sm1 C3 C2 30.9(8) . . . . ? N3 Sm1 C3 C2 -4.5(15) . . . . ? C2 C3 C4 C5 2.5(16) . . . . ? Sm1 C3 C4 C5 69.1(10) . . . . ? C2 C3 C4 Sm1 -66.6(11) . . . . ? C42 Sm1 C4 C5 176.6(9) 12 . . . ? N6 Sm1 C4 C5 176.6(9) 12 . . . ? C41 Sm1 C4 C5 134.6(8) 12 . . . ? N5 Sm1 C4 C5 134.6(8) 12 . . . ? N2 Sm1 C4 C5 37.7(7) . . . . ? N4 Sm1 C4 C5 -83.2(7) . . . . ? C41 Sm1 C4 C5 -167.4(8) 2 . . . ? N5 Sm1 C4 C5 -167.4(8) 2 . . . ? N6 Sm1 C4 C5 120.4(8) . . . . ? N1 Sm1 C4 C5 -42.7(7) . . . . ? N3 Sm1 C4 C5 6.4(12) . . . . ? C42 Sm1 C4 C3 -70.0(9) 12 . . . ? N6 Sm1 C4 C3 -70.0(9) 12 . . . ? C41 Sm1 C4 C3 -112.0(9) 12 . . . ? N5 Sm1 C4 C3 -112.0(9) 12 . . . ? N2 Sm1 C4 C3 151.2(8) . . . . ? N4 Sm1 C4 C3 30.3(9) . . . . ? C41 Sm1 C4 C3 -53.9(8) 2 . . . ? N5 Sm1 C4 C3 -53.9(8) 2 . . . ? N6 Sm1 C4 C3 -126.2(8) . . . . ? N1 Sm1 C4 C3 70.8(8) . . . . ? N3 Sm1 C4 C3 119.9(9) . . . . ? C3 C4 C5 C6 175.7(16) . . . . ? Sm1 C4 C5 C6 -113.6(16) . . . . ? C3 C4 C5 N1 -6.2(14) . . . . ? Sm1 C4 C5 N1 64.5(7) . . . . ? C3 C4 C5 Sm1 -70.7(10) . . . . ? C2 N1 C5 C4 8.4(14) . . . . ? C1 N1 C5 C4 -175.7(9) . . . . ? Sm1 N1 C5 C4 -70.3(9) . . . . ? C2 N1 C5 C6 -173.4(15) . . . . ? C1 N1 C5 C6 2.5(18) . . . . ? Sm1 N1 C5 C6 107.9(14) . . . . ? C2 N1 C5 Sm1 78.7(9) . . . . ? C1 N1 C5 Sm1 -105.4(7) . . . . ? C42 Sm1 C5 C4 -3.5(9) 12 . . . ? N6 Sm1 C5 C4 -3.5(9) 12 . . . ? C41 Sm1 C5 C4 -42.6(8) 12 . . . ? N5 Sm1 C5 C4 -42.6(8) 12 . . . ? N2 Sm1 C5 C4 -136.3(8) . . . . ? N4 Sm1 C5 C4 104.6(7) . . . . ? C41 Sm1 C5 C4 13.3(8) 2 . . . ? N5 Sm1 C5 C4 13.3(8) 2 . . . ? N6 Sm1 C5 C4 -58.2(8) . . . . ? N1 Sm1 C5 C4 110.4(9) . . . . ? N3 Sm1 C5 C4 -176.4(7) . . . . ? C42 Sm1 C5 C6 125.0(11) 12 . . . ? N6 Sm1 C5 C6 125.0(11) 12 . . . ? C41 Sm1 C5 C6 85.9(10) 12 . . . ? N5 Sm1 C5 C6 85.9(10) 12 . . . ? N2 Sm1 C5 C6 -7.8(9) . . . . ? N4 Sm1 C5 C6 -126.8(10) . . . . ? C41 Sm1 C5 C6 141.8(10) 2 . . . ? N5 Sm1 C5 C6 141.8(10) 2 . . . ? N6 Sm1 C5 C6 70.3(10) . . . . ? N1 Sm1 C5 C6 -121.1(12) . . . . ? N3 Sm1 C5 C6 -47.9(11) . . . . ? C42 Sm1 C5 N1 -113.9(6) 12 . . . ? N6 Sm1 C5 N1 -113.9(6) 12 . . . ? C41 Sm1 C5 N1 -153.0(6) 12 . . . ? N5 Sm1 C5 N1 -153.0(6) 12 . . . ? N2 Sm1 C5 N1 113.3(6) . . . . ? N4 Sm1 C5 N1 -5.8(6) . . . . ? C41 Sm1 C5 N1 -97.1(5) 2 . . . ? N5 Sm1 C5 N1 -97.1(5) 2 . . . ? N6 Sm1 C5 N1 -168.6(5) . . . . ? N3 Sm1 C5 N1 73.1(6) . . . . ? C4 C5 C6 C10 115.6(17) . . . . ? N1 C5 C6 C10 -62.1(18) . . . . ? Sm1 C5 C6 C10 20.4(15) . . . . ? C4 C5 C6 C7 -119.7(15) . . . . ? N1 C5 C6 C7 62.6(19) . . . . ? Sm1 C5 C6 C7 145.1(9) . . . . ? C4 C5 C6 C9 -2(2) . . . . ? N1 C5 C6 C9 -179.4(12) . . . . ? Sm1 C5 C6 C9 -97.0(13) . . . . ? C5 C6 C7 C8 47.9(16) . . . . ? C10 C6 C7 C8 170.7(11) . . . . ? C9 C6 C7 C8 -70.6(14) . . . . ? C5 C6 C9 C23A -172.4(12) . . . 11 ? C10 C6 C9 C23A 69.2(14) . . . 11 ? C7 C6 C9 C23A -52.5(14) . . . 11 ? C13 N2 C10 C6 -169.1(11) . . . . ? Sm1 N2 C10 C6 25.1(17) . . . . ? C13 N2 C10 C11 -2.4(11) . . . . ? Sm1 N2 C10 C11 -168.2(7) . . . . ? C5 C6 C10 N2 -29.2(18) . . . . ? C7 C6 C10 N2 -152.8(11) . . . . ? C9 C6 C10 N2 88.7(15) . . . . ? C5 C6 C10 C11 167.0(11) . . . . ? C7 C6 C10 C11 43.4(18) . . . . ? C9 C6 C10 C11 -75.1(16) . . . . ? N2 C10 C11 C12 15.1(11) . . . . ? C6 C10 C11 C12 -179.5(13) . . . . ? C10 C11 C12 C13 -22.3(9) . . . . ? C11 C12 C13 N4 -24.3(9) . . . 11 ? C11 C12 C13 C14 179.8(9) . . . . ? C11 C12 C13 N2 23.2(10) . . . . ? C10 N2 C13 C12 -11.7(11) . . . . ? Sm1 N2 C13 C12 153.3(7) . . . . ? C10 N2 C13 N4 74.1(10) . . . 11 ? Sm1 N2 C13 N4 -120.8(11) . . . 11 ? C10 N2 C13 C14 -173.8(9) . . . . ? Sm1 N2 C13 C14 -8.8(11) . . . . ? C12 C13 C14 C29 140.5(11) . . . 11 ? N4 C13 C14 C29 -12.0(14) 11 . . 11 ? N2 C13 C14 C29 -62.9(12) . . . 11 ? C12 C13 C14 C2 140.5(11) . . . 11 ? N4 C13 C14 C2 -12.0(14) 11 . . 11 ? N2 C13 C14 C2 -62.9(12) . . . 11 ? C12 C13 C14 C18 -148.2(9) . . . . ? N4 C13 C14 C18 59.4(13) 11 . . . ? N2 C13 C14 C18 8.5(12) . . . . ? C12 C13 C14 C15 -1.9(13) . . . . ? N4 C13 C14 C15 -154.4(8) 11 . . . ? N2 C13 C14 C15 154.7(7) . . . . ? C12 C13 C14 C27 -107.8(10) . . . 11 ? N4 C13 C14 C27 99.8(10) 11 . . 11 ? N2 C13 C14 C27 48.9(9) . . . 11 ? C29 C14 C15 C16 38.7(13) 11 . . . ? C2 C14 C15 C16 38.7(13) 11 . . . ? C18 C14 C15 C16 -29.2(12) . . . . ? C13 C14 C15 C16 -178.0(9) . . . . ? C27 C14 C15 C16 -77.7(11) 11 . . . ? C21 N3 C18 C19 -3.2(16) . . . . ? C17 N3 C18 C19 176.9(11) . . . . ? Sm1 N3 C18 C19 71.5(10) . . . . ? C21 N3 C18 C29 161(7) . . . 11 ? C17 N3 C18 C29 -19(8) . . . 11 ? Sm1 N3 C18 C29 -124(7) . . . 11 ? C21 N3 C18 C14 176.2(10) . . . . ? C17 N3 C18 C14 -3.6(16) . . . . ? Sm1 N3 C18 C14 -109.1(10) . . . . ? C21 N3 C18 Sm1 -74.7(9) . . . . ? C17 N3 C18 Sm1 105.5(10) . . . . ? C29 C14 C18 C19 2.6(18) 11 . . . ? C2 C14 C18 C19 2.6(18) 11 . . . ? C13 C14 C18 C19 -104.5(19) . . . . ? C15 C14 C18 C19 110.1(18) . . . . ? C27 C14 C18 C19 -166(2) 11 . . . ? C2 C14 C18 C29 0.0 11 . . 11 ? C13 C14 C18 C29 -107.2(12) . . . 11 ? C15 C14 C18 C29 107.4(11) . . . 11 ? C27 C14 C18 C29 -168.7(14) 11 . . 11 ? C29 C14 C18 N3 -176.6(15) 11 . . . ? C2 C14 C18 N3 -176.6(15) 11 . . . ? C13 C14 C18 N3 76.3(13) . . . . ? C15 C14 C18 N3 -69.2(13) . . . . ? C27 C14 C18 N3 14.7(11) 11 . . . ? C29 C14 C18 Sm1 102.0(10) 11 . . . ? C2 C14 C18 Sm1 102.0(10) 11 . . . ? C13 C14 C18 Sm1 -5.2(11) . . . . ? C15 C14 C18 Sm1 -150.6(6) . . . . ? C27 C14 C18 Sm1 -66.7(10) 11 . . . ? C42 Sm1 C18 C19 10.5(11) 12 . . . ? N6 Sm1 C18 C19 10.5(11) 12 . . . ? C41 Sm1 C18 C19 46.9(10) 12 . . . ? N5 Sm1 C18 C19 46.9(10) 12 . . . ? N2 Sm1 C18 C19 138.3(10) . . . . ? N4 Sm1 C18 C19 -102.2(9) . . . . ? C41 Sm1 C18 C19 -8.4(10) 2 . . . ? N5 Sm1 C18 C19 -8.4(10) 2 . . . ? N6 Sm1 C18 C19 53.8(9) . . . . ? N1 Sm1 C18 C19 -175.7(9) . . . . ? N3 Sm1 C18 C19 -112.3(12) . . . . ? C42 Sm1 C18 C29 -66.7(11) 12 . . 11 ? N6 Sm1 C18 C29 -66.7(11) 12 . . 11 ? C41 Sm1 C18 C29 -30.4(10) 12 . . 11 ? N5 Sm1 C18 C29 -30.4(10) 12 . . 11 ? N2 Sm1 C18 C29 61.0(9) . . . 11 ? N4 Sm1 C18 C29 -179.4(9) . . . 11 ? C41 Sm1 C18 C29 -85.6(10) 2 . . 11 ? N5 Sm1 C18 C29 -85.6(10) 2 . . 11 ? N6 Sm1 C18 C29 -23.5(9) . . . 11 ? N1 Sm1 C18 C29 107.1(9) . . . 11 ? N3 Sm1 C18 C29 170.5(14) . . . 11 ? C42 Sm1 C18 N3 122.7(9) 12 . . . ? N6 Sm1 C18 N3 122.7(9) 12 . . . ? C41 Sm1 C18 N3 159.1(8) 12 . . . ? N5 Sm1 C18 N3 159.1(8) 12 . . . ? N2 Sm1 C18 N3 -109.5(8) . . . . ? N4 Sm1 C18 N3 10.1(8) . . . . ? C41 Sm1 C18 N3 103.9(8) 2 . . . ? N5 Sm1 C18 N3 103.9(8) 2 . . . ? N6 Sm1 C18 N3 166.0(8) . . . . ? N1 Sm1 C18 N3 -63.4(9) . . . . ? C42 Sm1 C18 C14 -127.4(8) 12 . . . ? N6 Sm1 C18 C14 -127.4(8) 12 . . . ? C41 Sm1 C18 C14 -91.0(8) 12 . . . ? N5 Sm1 C18 C14 -91.0(8) 12 . . . ? N2 Sm1 C18 C14 0.3(7) . . . . ? N4 Sm1 C18 C14 119.9(7) . . . . ? C41 Sm1 C18 C14 -146.3(7) 2 . . . ? N5 Sm1 C18 C14 -146.3(7) 2 . . . ? N6 Sm1 C18 C14 -84.2(7) . . . . ? N1 Sm1 C18 C14 46.4(8) . . . . ? N3 Sm1 C18 C14 109.8(11) . . . . ? C29 C18 C19 C20 -175.7(14) 11 . . . ? N3 C18 C19 C20 1.4(17) . . . . ? C14 C18 C19 C20 -177.9(15) . . . . ? Sm1 C18 C19 C20 69.3(11) . . . . ? N3 C18 C19 C29 177.1(15) . . . 11 ? C14 C18 C19 C29 -2.2(15) . . . 11 ? Sm1 C18 C19 C29 -115.1(9) . . . 11 ? C29 C18 C19 Sm1 115.1(9) 11 . . . ? N3 C18 C19 Sm1 -67.9(9) . . . . ? C14 C18 C19 Sm1 112.9(17) . . . . ? C42 Sm1 C19 C18 -170.7(10) 12 . . . ? N6 Sm1 C19 C18 -170.7(10) 12 . . . ? C41 Sm1 C19 C18 -132.0(10) 12 . . . ? N5 Sm1 C19 C18 -132.0(10) 12 . . . ? N2 Sm1 C19 C18 -36.3(8) . . . . ? N4 Sm1 C19 C18 84.7(9) . . . . ? C41 Sm1 C19 C18 172.9(9) 2 . . . ? N5 Sm1 C19 C18 172.9(9) 2 . . . ? N6 Sm1 C19 C18 -119.8(10) . . . . ? N1 Sm1 C19 C18 8.0(16) . . . . ? N3 Sm1 C19 C18 38.2(7) . . . . ? C42 Sm1 C19 C20 74.2(9) 12 . . . ? N6 Sm1 C19 C20 74.2(9) 12 . . . ? C41 Sm1 C19 C20 112.9(9) 12 . . . ? N5 Sm1 C19 C20 112.9(9) 12 . . . ? N2 Sm1 C19 C20 -151.3(8) . . . . ? N4 Sm1 C19 C20 -30.3(9) . . . . ? C41 Sm1 C19 C20 57.8(8) 2 . . . ? N5 Sm1 C19 C20 57.8(8) 2 . . . ? N6 Sm1 C19 C20 125.2(9) . . . . ? N1 Sm1 C19 C20 -107.1(12) . . . . ? N3 Sm1 C19 C20 -76.8(9) . . . . ? C42 Sm1 C19 C29 -127.1(8) 12 . . 11 ? N6 Sm1 C19 C29 -127.1(8) 12 . . 11 ? C41 Sm1 C19 C29 -88.4(8) 12 . . 11 ? N5 Sm1 C19 C29 -88.4(8) 12 . . 11 ? N2 Sm1 C19 C29 7.3(7) . . . 11 ? N4 Sm1 C19 C29 128.3(7) . . . 11 ? C41 Sm1 C19 C29 -143.5(7) 2 . . 11 ? N5 Sm1 C19 C29 -143.5(7) 2 . . 11 ? N6 Sm1 C19 C29 -76.2(7) . . . 11 ? N1 Sm1 C19 C29 51.6(14) . . . 11 ? N3 Sm1 C19 C29 81.8(8) . . . 11 ? C18 C19 C20 C21 0.9(17) . . . . ? C29 C19 C20 C21 -8(4) 11 . . . ? Sm1 C19 C20 C21 68.7(10) . . . . ? C18 C19 C20 Sm1 -67.8(11) . . . . ? C29 C19 C20 Sm1 -77(4) 11 . . . ? C42 Sm1 C20 C19 -104.3(9) 12 . . . ? N6 Sm1 C20 C19 -104.3(9) 12 . . . ? C41 Sm1 C20 C19 -64.1(9) 12 . . . ? N5 Sm1 C20 C19 -64.1(9) 12 . . . ? N2 Sm1 C20 C19 30.1(9) . . . . ? N4 Sm1 C20 C19 150.7(9) . . . . ? C41 Sm1 C20 C19 -121.0(9) 2 . . . ? N5 Sm1 C20 C19 -121.0(9) 2 . . . ? N6 Sm1 C20 C19 -49.1(8) . . . . ? N1 Sm1 C20 C19 126.7(8) . . . . ? N3 Sm1 C20 C19 75.6(9) . . . . ? C42 Sm1 C20 C21 142.1(8) 12 . . . ? N6 Sm1 C20 C21 142.1(8) 12 . . . ? C41 Sm1 C20 C21 -177.7(8) 12 . . . ? N5 Sm1 C20 C21 -177.7(8) 12 . . . ? N2 Sm1 C20 C21 -83.5(7) . . . . ? N4 Sm1 C20 C21 37.1(7) . . . . ? C41 Sm1 C20 C21 125.4(8) 2 . . . ? N5 Sm1 C20 C21 125.4(8) 2 . . . ? N6 Sm1 C20 C21 -162.7(8) . . . . ? N1 Sm1 C20 C21 13.1(10) . . . . ? N3 Sm1 C20 C21 -38.0(7) . . . . ? C19 C20 C21 N3 -2.8(16) . . . . ? Sm1 C20 C21 N3 66.1(9) . . . . ? C19 C20 C21 C22 176.3(15) . . . . ? Sm1 C20 C21 C22 -114.8(15) . . . . ? C19 C20 C21 Sm1 -68.9(11) . . . . ? C18 N3 C21 C20 3.7(15) . . . . ? C17 N3 C21 C20 -176.5(11) . . . . ? Sm1 N3 C21 C20 -69.9(10) . . . . ? C18 N3 C21 C22 -175.4(13) . . . . ? C17 N3 C21 C22 4(2) . . . . ? Sm1 N3 C21 C22 111.0(13) . . . . ? C18 N3 C21 Sm1 73.6(9) . . . . ? C17 N3 C21 Sm1 -106.6(12) . . . . ? C42 Sm1 C21 C20 -39.3(9) 12 . . . ? N6 Sm1 C21 C20 -39.3(9) 12 . . . ? C41 Sm1 C21 C20 2.6(9) 12 . . . ? N5 Sm1 C21 C20 2.6(9) 12 . . . ? N2 Sm1 C21 C20 104.3(7) . . . . ? N4 Sm1 C21 C20 -136.5(8) . . . . ? C41 Sm1 C21 C20 -53.8(7) 2 . . . ? N5 Sm1 C21 C20 -53.8(7) 2 . . . ? N6 Sm1 C21 C20 18.5(8) . . . . ? N1 Sm1 C21 C20 -172.1(6) . . . . ? N3 Sm1 C21 C20 111.8(11) . . . . ? C42 Sm1 C21 N3 -151.1(8) 12 . . . ? N6 Sm1 C21 N3 -151.1(8) 12 . . . ? C41 Sm1 C21 N3 -109.2(8) 12 . . . ? N5 Sm1 C21 N3 -109.2(8) 12 . . . ? N2 Sm1 C21 N3 -7.6(8) . . . . ? N4 Sm1 C21 N3 111.6(8) . . . . ? C41 Sm1 C21 N3 -165.7(7) 2 . . . ? N5 Sm1 C21 N3 -165.7(7) 2 . . . ? N6 Sm1 C21 N3 -93.3(7) . . . . ? N1 Sm1 C21 N3 76.1(7) . . . . ? C42 Sm1 C21 C22 89.5(10) 12 . . . ? N6 Sm1 C21 C22 89.5(10) 12 . . . ? C41 Sm1 C21 C22 131.4(9) 12 . . . ? N5 Sm1 C21 C22 131.4(9) 12 . . . ? N2 Sm1 C21 C22 -127.0(9) . . . . ? N4 Sm1 C21 C22 -7.8(8) . . . . ? C41 Sm1 C21 C22 74.9(9) 2 . . . ? N5 Sm1 C21 C22 74.9(9) 2 . . . ? N6 Sm1 C21 C22 147.3(9) . . . . ? N1 Sm1 C21 C22 -43.4(10) . . . . ? N3 Sm1 C21 C22 -119.4(12) . . . . ? C20 C21 C22 C23 -109.2(17) . . . . ? N3 C21 C22 C23 69.7(17) . . . . ? Sm1 C21 C22 C23 155.0(9) . . . . ? C20 C21 C22 C26 118.1(16) . . . . ? N3 C21 C22 C26 -62.9(17) . . . . ? Sm1 C21 C22 C26 22.3(13) . . . . ? C20 C21 C22 C25 0(2) . . . 12 ? N3 C21 C22 C25 179.1(14) . . . 12 ? Sm1 C21 C22 C25 -95.6(13) . . . 12 ? C21 C22 C23 C24 45(2) . . . . ? C26 C22 C23 C24 167.5(15) . . . . ? C25 C22 C23 C24 -68(2) 12 . . . ? C13 N4 C26 C11A -4.5(13) 12 . . 12 ? Sm1 N4 C26 C11A -167.5(8) . . . 12 ? C13 N4 C26 C22 -166.7(10) 12 . . . ? Sm1 N4 C26 C22 30.3(15) . . . . ? C23 C22 C26 C11A 48.3(19) . . . 12 ? C21 C22 C26 C11A 168.6(12) . . . 12 ? C25 C22 C26 C11A -74.3(17) 12 . . 12 ? C23 C22 C26 N4 -153.4(11) . . . . ? C21 C22 C26 N4 -33.0(15) . . . . ? C25 C22 C26 N4 84.1(14) 12 . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.23 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 2.528 _refine_diff_density_min -1.163 _refine_diff_density_rms 0.135 # Attachment 'compound_3.cif' data_c:smtbutbu _database_code_depnum_ccdc_archive 'CCDC 765857' #TrackingRef 'compound_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C47 H72 N5 Sm)' _chemical_formula_sum 'C47 H72 N5 Sm' _chemical_formula_weight 857.45 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' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Cmcm _symmetry_space_group_name_Hall '-C 2c 2' _symmetry_Int_Tables_number 63 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, 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' '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, y, z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z-1/2' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.06(6) _cell_length_b 10.493(7) _cell_length_c 19.3928(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4286(13) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 23 _cell_measurement_theta_min 7.42 _cell_measurement_theta_max 10.20 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1804 _exptl_absorpt_coefficient_mu 1.408 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.5903 _exptl_absorpt_correction_T_max 0.6307 _exptl_absorpt_process_details ? _exptl_special_details ; ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius TurboCAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 3 _diffrn_reflns_number 1986 _diffrn_reflns_av_R_equivalents 0.0772 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.04 _reflns_number_total 1971 _reflns_number_gt 1814 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf-Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf-Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; X-SEED (Barbour, 2001) and ORTEPIII (Farrugia, 1997) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All hydrogens were calculated using the riding model of shelxl. Disorder was apparent in the coordinating CN and the tert-butyl groups. The CN disorder was resolved by superimposing 50% occupancy atoms at the same site (EXYZ card) with the same anisotropic displacement parameters (EADP card). The tert-butyl disorder was modelled using a 50% site occupancy 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^)+(0.1340P)^2^+120.1107P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1971 _refine_ls_number_parameters 132 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0901 _refine_ls_R_factor_gt 0.0832 _refine_ls_wR_factor_ref 0.2174 _refine_ls_wR_factor_gt 0.2106 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sm1 Sm 0.5000 0.08618(8) 0.7500 0.0207(4) Uani 1 4 d S . . N1 N 0.5000 0.2337(9) 0.6297(5) 0.024(2) Uani 1 2 d S . . N2 N 0.3917(5) 0.2014(10) 0.7500 0.025(2) Uani 1 2 d S . . N3 N 0.4687(5) -0.1334(12) 0.7500 0.027(2) Uani 0.50 2 d SP . . C1 C 0.4657(4) 0.0405(9) 0.6049(4) 0.0282(18) Uani 1 1 d . . . H1 H 0.4394 -0.0314 0.5966 0.034 Uiso 1 1 calc R . . C2 C 0.4451(4) 0.1603(8) 0.6187(4) 0.0225(17) Uani 1 1 d . . . C3 C 0.3782(4) 0.2128(9) 0.6209(5) 0.030(2) Uani 1 1 d . . . C4 C 0.3640(4) 0.2590(9) 0.6928(5) 0.0307(19) Uani 1 1 d . . . C5 C 0.3224(4) 0.3537(9) 0.7131(6) 0.038(2) Uani 1 1 d . . . H5 H 0.2985 0.4082 0.6839 0.046 Uiso 1 1 calc R . . C6 C 0.3689(5) 0.3206(12) 0.5668(5) 0.044(3) Uani 1 1 d . . . H6A H 0.3236 0.3456 0.5665 0.053 Uiso 1 1 calc R . . H6B H 0.3938 0.3957 0.5816 0.053 Uiso 1 1 calc R . . C7 C 0.3883(6) 0.2865(14) 0.4939(6) 0.064(4) Uani 1 1 d . . . H7A H 0.3812 0.3598 0.4636 0.096 Uiso 1 1 calc R . . H7B H 0.3628 0.2142 0.4778 0.096 Uiso 1 1 calc R . . H7C H 0.4334 0.2633 0.4932 0.096 Uiso 1 1 calc R . . C8 C 0.3332(5) 0.0990(10) 0.6041(6) 0.042(2) Uani 1 1 d . . . H8A H 0.3457 0.0625 0.5591 0.050 Uiso 1 1 calc R . . H8B H 0.3394 0.0321 0.6395 0.050 Uiso 1 1 calc R . . C9 C 0.2625(5) 0.1338(16) 0.6015(8) 0.064(4) Uani 1 1 d . . . H9A H 0.2375 0.0575 0.5909 0.096 Uiso 1 1 calc R . . H9B H 0.2555 0.1982 0.5656 0.096 Uiso 1 1 calc R . . H9C H 0.2493 0.1681 0.6463 0.096 Uiso 1 1 calc R . . C10 C 0.5000 0.3672(11) 0.6461(7) 0.031(3) Uani 1 2 d S . . H10A H 0.5402 0.3898 0.6684 0.047 Uiso 0.50 1 calc PR . . H10B H 0.4647 0.3860 0.6774 0.047 Uiso 0.50 1 calc PR . . H10C H 0.4951 0.4169 0.6036 0.047 Uiso 0.50 1 calc PR . . C11 C 0.4687(5) -0.1334(12) 0.7500 0.027(2) Uani 0.50 2 d SP . . C12 C 0.4187(6) -0.2310(13) 0.7500 0.032(3) Uani 1 2 d S . . C13 C 0.4336(10) -0.347(2) 0.7989(11) 0.043(5) Uiso 0.50 1 d P . . H13A H 0.4737 -0.3868 0.7848 0.064 Uiso 0.50 1 calc PR . . H13B H 0.3992 -0.4096 0.7957 0.064 Uiso 0.50 1 calc PR . . H13C H 0.4372 -0.3168 0.8465 0.064 Uiso 0.50 1 calc PR . . C14 C 0.4075(10) -0.289(2) 0.6767(10) 0.040(5) Uiso 0.50 1 d P . . H14A H 0.4483 -0.2976 0.6529 0.060 Uiso 0.50 1 calc PR . . H14B H 0.3797 -0.2322 0.6502 0.060 Uiso 0.50 1 calc PR . . H14C H 0.3875 -0.3726 0.6812 0.060 Uiso 0.50 1 calc PR . . C15 C 0.3619(10) -0.170(2) 0.7726(10) 0.044(5) Uiso 0.50 1 d P . . H15A H 0.3483 -0.1080 0.7378 0.067 Uiso 0.50 1 calc PR . . H15B H 0.3699 -0.1262 0.8164 0.067 Uiso 0.50 1 calc PR . . H15C H 0.3286 -0.2341 0.7790 0.067 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sm1 0.0138(5) 0.0210(5) 0.0273(5) 0.000 0.000 0.000 N1 0.023(5) 0.023(5) 0.027(5) -0.002(4) 0.000 0.000 N2 0.014(5) 0.028(5) 0.034(5) 0.000 0.000 -0.002(4) N3 0.020(5) 0.039(6) 0.021(5) 0.000 0.000 0.011(5) C1 0.021(4) 0.035(5) 0.028(4) -0.002(4) -0.004(4) -0.002(4) C2 0.017(4) 0.027(4) 0.024(4) 0.002(3) -0.001(3) 0.000(3) C3 0.020(4) 0.038(5) 0.032(5) 0.005(4) -0.002(4) 0.005(4) C4 0.021(4) 0.038(5) 0.033(4) 0.004(4) -0.005(4) -0.001(4) C5 0.023(4) 0.036(5) 0.056(6) 0.009(5) 0.000(4) 0.014(4) C6 0.026(5) 0.063(7) 0.043(6) 0.028(5) 0.002(4) 0.011(5) C7 0.051(7) 0.093(10) 0.047(6) 0.027(7) 0.005(6) 0.026(7) C8 0.021(5) 0.061(7) 0.043(6) 0.011(5) -0.009(4) -0.004(4) C9 0.021(5) 0.101(10) 0.071(8) 0.004(8) -0.010(5) -0.010(6) C10 0.035(7) 0.017(6) 0.042(7) -0.002(5) 0.000 0.000 C11 0.020(5) 0.039(6) 0.021(5) 0.000 0.000 0.011(5) C12 0.030(7) 0.036(7) 0.030(6) 0.000 0.000 -0.010(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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.0000 (0.0001) x - 2.3539 (0.0634) y + 18.8986 (0.0602) z = 11.3306 (0.0413) * 0.0189 (0.0069) N1 * 0.0059 (0.0021) C1 * -0.0153 (0.0056) C2 * 0.0059 (0.0021) C1_$2 * -0.0153 (0.0056) C2_$2 -0.0983 (0.0115) C3 0.0148 (0.0217) C10 Rms deviation of fitted atoms = 0.0134 - 0.0000 (0.0002) x + 10.4935 (0.0299) y + 0.0000 (0.0003) z = 2.2333 (0.0111) Angle to previous plane (with approximate esd) = 77.04 ( 0.39 ) * 0.0000 (0.0001) C3 * 0.0000 (0.0001) C3_$2 * 0.0000 (0.0001) C3_$3 * 0.0000 (0.0000) C3_$4 -1.3290 (0.0102) Sm1 Rms deviation of fitted atoms = 0.0000 15.6222 (0.1044) x + 7.0353 (0.0558) y - 0.0000 (0.0014) z = 7.5209 (0.0291) Angle to previous plane (with approximate esd) = 47.90 ( 0.40 ) * 0.0151 (0.0074) N2 * -0.0123 (0.0061) C4 * 0.0048 (0.0023) C5 * 0.0048 (0.0023) C5_$3 * -0.0123 (0.0061) C4_$3 -0.1158 (0.0119) C3 Rms deviation of fitted atoms = 0.0107 ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sm1 N3 2.397(13) . ? Sm1 C11 2.397(13) 11_655 ? Sm1 N3 2.397(13) 11_655 ? Sm1 N2 2.581(11) 11_655 ? Sm1 N2 2.581(11) . ? Sm1 N1 2.801(10) 10_557 ? Sm1 N1 2.801(10) . ? Sm1 C2 2.903(8) 10_557 ? Sm1 C2 2.903(8) 4_656 ? Sm1 C2 2.903(8) . ? Sm1 C2 2.903(8) 11_655 ? N1 C2 1.405(10) . ? N1 C2 1.405(10) 11_655 ? N1 C10 1.436(15) . ? N2 C4 1.391(11) 10_557 ? N2 C4 1.391(11) . ? N3 C11 1.32(2) 11_655 ? N3 N3 1.32(2) 11_655 ? N3 C12 1.468(18) . ? C1 C2 1.357(12) . ? C1 C1 1.443(17) 11_655 ? C1 H1 0.9500 . ? C2 C3 1.514(12) . ? C3 C4 1.507(13) . ? C3 C6 1.554(13) . ? C3 C8 1.558(14) . ? C4 C5 1.382(13) . ? C5 C5 1.43(2) 10_557 ? C5 H5 0.9500 . ? C6 C7 1.513(16) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.534(15) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C12 C15 1.43(2) 10_557 ? C12 C15 1.43(2) . ? C12 C14 1.56(2) . ? C12 C14 1.56(2) 10_557 ? C12 C13 1.57(2) 10_557 ? C12 C13 1.57(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 Sm1 C11 32.0(5) . 11_655 ? N3 Sm1 N3 32.0(5) . 11_655 ? C11 Sm1 N3 0.00(16) 11_655 11_655 ? N3 Sm1 N2 133.9(3) . 11_655 ? C11 Sm1 N2 102.0(4) 11_655 11_655 ? N3 Sm1 N2 102.0(4) 11_655 11_655 ? N3 Sm1 N2 102.0(4) . . ? C11 Sm1 N2 133.9(3) 11_655 . ? N3 Sm1 N2 133.9(3) 11_655 . ? N2 Sm1 N2 124.1(5) 11_655 . ? N3 Sm1 N1 122.1(2) . 10_557 ? C11 Sm1 N1 122.1(2) 11_655 10_557 ? N3 Sm1 N1 122.1(2) 11_655 10_557 ? N2 Sm1 N1 74.99(14) 11_655 10_557 ? N2 Sm1 N1 74.99(14) . 10_557 ? N3 Sm1 N1 122.1(2) . . ? C11 Sm1 N1 122.1(2) 11_655 . ? N3 Sm1 N1 122.1(2) 11_655 . ? N2 Sm1 N1 74.99(14) 11_655 . ? N2 Sm1 N1 74.99(14) . . ? N1 Sm1 N1 112.9(4) 10_557 . ? N3 Sm1 C2 98.5(2) . 10_557 ? C11 Sm1 C2 111.55(19) 11_655 10_557 ? N3 Sm1 C2 111.55(19) 11_655 10_557 ? N2 Sm1 C2 103.1(2) 11_655 10_557 ? N2 Sm1 C2 61.48(17) . 10_557 ? N1 Sm1 C2 28.5(2) 10_557 10_557 ? N1 Sm1 C2 125.6(2) . 10_557 ? N3 Sm1 C2 111.55(19) . 4_656 ? C11 Sm1 C2 98.5(2) 11_655 4_656 ? N3 Sm1 C2 98.5(2) 11_655 4_656 ? N2 Sm1 C2 61.48(17) 11_655 4_656 ? N2 Sm1 C2 103.1(2) . 4_656 ? N1 Sm1 C2 28.5(2) 10_557 4_656 ? N1 Sm1 C2 125.6(2) . 4_656 ? C2 Sm1 C2 46.9(3) 10_557 4_656 ? N3 Sm1 C2 98.5(2) . . ? C11 Sm1 C2 111.55(19) 11_655 . ? N3 Sm1 C2 111.55(19) 11_655 . ? N2 Sm1 C2 103.1(2) 11_655 . ? N2 Sm1 C2 61.48(17) . . ? N1 Sm1 C2 125.6(2) 10_557 . ? N1 Sm1 C2 28.5(2) . . ? C2 Sm1 C2 122.6(3) 10_557 . ? C2 Sm1 C2 148.9(3) 4_656 . ? N3 Sm1 C2 111.55(19) . 11_655 ? C11 Sm1 C2 98.5(2) 11_655 11_655 ? N3 Sm1 C2 98.5(2) 11_655 11_655 ? N2 Sm1 C2 61.48(17) 11_655 11_655 ? N2 Sm1 C2 103.1(2) . 11_655 ? N1 Sm1 C2 125.6(2) 10_557 11_655 ? N1 Sm1 C2 28.5(2) . 11_655 ? C2 Sm1 C2 148.9(3) 10_557 11_655 ? C2 Sm1 C2 122.6(3) 4_656 11_655 ? C2 Sm1 C2 46.9(3) . 11_655 ? C2 N1 C2 110.7(9) . 11_655 ? C2 N1 C10 124.6(5) . . ? C2 N1 C10 124.6(5) 11_655 . ? C2 N1 Sm1 79.8(5) . . ? C2 N1 Sm1 79.8(5) 11_655 . ? C10 N1 Sm1 110.8(8) . . ? C4 N2 C4 105.7(10) 10_557 . ? C4 N2 Sm1 125.0(5) 10_557 . ? C4 N2 Sm1 125.0(5) . . ? C11 N3 N3 0.0(11) 11_655 11_655 ? C11 N3 C12 135.8(7) 11_655 . ? N3 N3 C12 135.8(7) 11_655 . ? C11 N3 Sm1 74.0(3) 11_655 . ? N3 N3 Sm1 74.0(3) 11_655 . ? C12 N3 Sm1 150.2(9) . . ? C2 C1 C1 108.7(5) . 11_655 ? C2 C1 Sm1 74.9(5) . . ? C1 C1 Sm1 75.81(17) 11_655 . ? C2 C1 H1 125.7 . . ? C1 C1 H1 125.7 11_655 . ? Sm1 C1 H1 115.7 . . ? C1 C2 N1 105.9(7) . . ? C1 C2 C3 129.9(8) . . ? N1 C2 C3 124.2(7) . . ? C1 C2 Sm1 78.3(5) . . ? N1 C2 Sm1 71.7(5) . . ? C3 C2 Sm1 116.4(5) . . ? C4 C3 C2 109.1(7) . . ? C4 C3 C6 111.5(8) . . ? C2 C3 C6 111.3(7) . . ? C4 C3 C8 108.6(8) . . ? C2 C3 C8 106.3(8) . . ? C6 C3 C8 110.0(8) . . ? C5 C4 N2 110.5(8) . . ? C5 C4 C3 128.4(8) . . ? N2 C4 C3 121.0(8) . . ? C4 C5 C5 106.6(6) . 10_557 ? C4 C5 H5 126.7 . . ? C5 C5 H5 126.7 10_557 . ? C7 C6 C3 115.1(9) . . ? C7 C6 H6A 108.5 . . ? C3 C6 H6A 108.5 . . ? C7 C6 H6B 108.5 . . ? C3 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C3 114.5(10) . . ? C9 C8 H8A 108.6 . . ? C3 C8 H8A 108.6 . . ? C9 C8 H8B 108.6 . . ? C3 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N1 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C15 C12 C15 35.8(16) 10_557 . ? C15 C12 N3 106.8(13) 10_557 . ? C15 C12 N3 106.8(13) . . ? C15 C12 C14 76.6(12) 10_557 . ? C15 C12 C14 109.1(13) . . ? N3 C12 C14 112.2(9) . . ? C15 C12 C14 109.1(13) 10_557 10_557 ? C15 C12 C14 76.6(12) . 10_557 ? N3 C12 C14 112.2(9) . 10_557 ? C14 C12 C14 130.8(18) . 10_557 ? C15 C12 C13 109.2(13) 10_557 10_557 ? C15 C12 C13 134.3(15) . 10_557 ? N3 C12 C13 113.4(11) . 10_557 ? C14 C12 C13 35.2(10) . 10_557 ? C14 C12 C13 106.1(14) 10_557 10_557 ? C15 C12 C13 134.3(15) 10_557 . ? C15 C12 C13 109.2(13) . . ? N3 C12 C13 113.4(11) . . ? C14 C12 C13 106.1(14) . . ? C14 C12 C13 35.2(10) 10_557 . ? C13 C12 C13 74.0(17) 10_557 . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 N3 Sm1 N1 C2 37.7(6) . . . . ? C11 Sm1 N1 C2 75.7(5) 11_655 . . . ? N3 Sm1 N1 C2 75.7(5) 11_655 . . . ? N2 Sm1 N1 C2 170.5(5) 11_655 . . . ? N2 Sm1 N1 C2 -57.1(5) . . . . ? N1 Sm1 N1 C2 -123.3(5) 10_557 . . . ? C2 Sm1 N1 C2 -94.0(6) 10_557 . . . ? C2 Sm1 N1 C2 -152.7(4) 4_656 . . . ? C2 Sm1 N1 C2 113.4(9) 11_655 . . . ? N3 Sm1 N1 C2 -75.7(5) . . . 11_655 ? C11 Sm1 N1 C2 -37.7(6) 11_655 . . 11_655 ? N3 Sm1 N1 C2 -37.7(6) 11_655 . . 11_655 ? N2 Sm1 N1 C2 57.1(5) 11_655 . . 11_655 ? N2 Sm1 N1 C2 -170.5(5) . . . 11_655 ? N1 Sm1 N1 C2 123.3(5) 10_557 . . 11_655 ? C2 Sm1 N1 C2 152.7(4) 10_557 . . 11_655 ? C2 Sm1 N1 C2 94.0(6) 4_656 . . 11_655 ? C2 Sm1 N1 C2 -113.4(9) . . . 11_655 ? N3 Sm1 N1 C10 161.0(3) . . . . ? C11 Sm1 N1 C10 -161.0(3) 11_655 . . . ? N3 Sm1 N1 C10 -161.0(3) 11_655 . . . ? N2 Sm1 N1 C10 -66.2(2) 11_655 . . . ? N2 Sm1 N1 C10 66.2(2) . . . . ? N1 Sm1 N1 C10 0.000(3) 10_557 . . . ? C2 Sm1 N1 C10 29.3(2) 10_557 . . . ? C2 Sm1 N1 C10 -29.3(2) 4_656 . . . ? C2 Sm1 N1 C10 123.3(5) . . . . ? C2 Sm1 N1 C10 -123.3(5) 11_655 . . . ? N3 Sm1 N2 C4 103.2(8) . . . 10_557 ? C11 Sm1 N2 C4 103.2(8) 11_655 . . 10_557 ? N3 Sm1 N2 C4 103.2(8) 11_655 . . 10_557 ? N2 Sm1 N2 C4 -76.8(8) 11_655 . . 10_557 ? N1 Sm1 N2 C4 -17.1(8) 10_557 . . 10_557 ? N1 Sm1 N2 C4 -136.4(9) . . . 10_557 ? C2 Sm1 N2 C4 10.0(7) 10_557 . . 10_557 ? C2 Sm1 N2 C4 -12.5(9) 4_656 . . 10_557 ? C2 Sm1 N2 C4 -163.5(9) . . . 10_557 ? C2 Sm1 N2 C4 -141.0(8) 11_655 . . 10_557 ? N3 Sm1 N2 C4 -103.2(8) . . . . ? C11 Sm1 N2 C4 -103.2(8) 11_655 . . . ? N3 Sm1 N2 C4 -103.2(8) 11_655 . . . ? N2 Sm1 N2 C4 76.8(8) 11_655 . . . ? N1 Sm1 N2 C4 136.4(9) 10_557 . . . ? N1 Sm1 N2 C4 17.1(8) . . . . ? C2 Sm1 N2 C4 163.5(9) 10_557 . . . ? C2 Sm1 N2 C4 141.0(8) 4_656 . . . ? C2 Sm1 N2 C4 -10.0(7) . . . . ? C2 Sm1 N2 C4 12.5(9) 11_655 . . . ? N3 Sm1 N3 C11 0.0 11_655 . . 11_655 ? N2 Sm1 N3 C11 0.0 11_655 . . 11_655 ? N2 Sm1 N3 C11 180.0 . . . 11_655 ? N1 Sm1 N3 C11 -100.35(18) 10_557 . . 11_655 ? N1 Sm1 N3 C11 100.35(18) . . . 11_655 ? C2 Sm1 N3 C11 -117.50(17) 10_557 . . 11_655 ? C2 Sm1 N3 C11 -70.6(2) 4_656 . . 11_655 ? C2 Sm1 N3 C11 117.50(17) . . . 11_655 ? C2 Sm1 N3 C11 70.6(2) 11_655 . . 11_655 ? C11 Sm1 N3 N3 0.0 11_655 . . 11_655 ? N2 Sm1 N3 N3 0.0 11_655 . . 11_655 ? N2 Sm1 N3 N3 180.0 . . . 11_655 ? N1 Sm1 N3 N3 -100.35(18) 10_557 . . 11_655 ? N1 Sm1 N3 N3 100.35(18) . . . 11_655 ? C2 Sm1 N3 N3 -117.50(17) 10_557 . . 11_655 ? C2 Sm1 N3 N3 -70.6(2) 4_656 . . 11_655 ? C2 Sm1 N3 N3 117.50(17) . . . 11_655 ? C2 Sm1 N3 N3 70.6(2) 11_655 . . 11_655 ? C11 Sm1 N3 C12 180.0 11_655 . . . ? N3 Sm1 N3 C12 180.0 11_655 . . . ? N2 Sm1 N3 C12 180.0 11_655 . . . ? N2 Sm1 N3 C12 0.0 . . . . ? N1 Sm1 N3 C12 79.65(18) 10_557 . . . ? N1 Sm1 N3 C12 -79.65(18) . . . . ? C2 Sm1 N3 C12 62.50(17) 10_557 . . . ? C2 Sm1 N3 C12 109.4(2) 4_656 . . . ? C2 Sm1 N3 C12 -62.50(17) . . . . ? C2 Sm1 N3 C12 -109.4(2) 11_655 . . . ? N3 Sm1 C1 C2 142.3(6) . . . . ? C11 Sm1 C1 C2 173.7(5) 11_655 . . . ? N3 Sm1 C1 C2 173.7(5) 11_655 . . . ? N2 Sm1 C1 C2 -85.4(5) 11_655 . . . ? N2 Sm1 C1 C2 38.0(5) . . . . ? N1 Sm1 C1 C2 4.7(8) 10_557 . . . ? N1 Sm1 C1 C2 -38.8(4) . . . . ? C2 Sm1 C1 C2 54.9(6) 10_557 . . . ? C2 Sm1 C1 C2 -78.6(14) 4_656 . . . ? C2 Sm1 C1 C2 -79.2(7) 11_655 . . . ? N3 Sm1 C1 C1 -103.5(3) . . . 11_655 ? C11 Sm1 C1 C1 -72.1(3) 11_655 . . 11_655 ? N3 Sm1 C1 C1 -72.1(3) 11_655 . . 11_655 ? N2 Sm1 C1 C1 28.9(2) 11_655 . . 11_655 ? N2 Sm1 C1 C1 152.2(2) . . . 11_655 ? N1 Sm1 C1 C1 118.9(4) 10_557 . . 11_655 ? N1 Sm1 C1 C1 75.4(2) . . . 11_655 ? C2 Sm1 C1 C1 169.1(4) 10_557 . . 11_655 ? C2 Sm1 C1 C1 35.6(11) 4_656 . . 11_655 ? C2 Sm1 C1 C1 114.2(5) . . . 11_655 ? C2 Sm1 C1 C1 35.0(3) 11_655 . . 11_655 ? C1 C1 C2 N1 -2.0(7) 11_655 . . . ? Sm1 C1 C2 N1 66.9(6) . . . . ? C1 C1 C2 C3 176.4(7) 11_655 . . . ? Sm1 C1 C2 C3 -114.7(9) . . . . ? C1 C1 C2 Sm1 -68.9(2) 11_655 . . . ? C2 N1 C2 C1 3.4(12) 11_655 . . . ? C10 N1 C2 C1 -179.8(11) . . . . ? Sm1 N1 C2 C1 -71.6(6) . . . . ? C2 N1 C2 C3 -175.1(5) 11_655 . . . ? C10 N1 C2 C3 1.7(16) . . . . ? Sm1 N1 C2 C3 110.0(8) . . . . ? C2 N1 C2 Sm1 74.9(8) 11_655 . . . ? C10 N1 C2 Sm1 -108.3(11) . . . . ? N3 Sm1 C2 C1 -37.1(6) . . . . ? C11 Sm1 C2 C1 -6.8(6) 11_655 . . . ? N3 Sm1 C2 C1 -6.8(6) 11_655 . . . ? N2 Sm1 C2 C1 101.9(5) 11_655 . . . ? N2 Sm1 C2 C1 -136.1(6) . . . . ? N1 Sm1 C2 C1 -177.3(4) 10_557 . . . ? N1 Sm1 C2 C1 111.3(7) . . . . ? C2 Sm1 C2 C1 -142.9(4) 10_557 . . . ? C2 Sm1 C2 C1 157.6(5) 4_656 . . . ? C2 Sm1 C2 C1 74.5(5) 11_655 . . . ? N3 Sm1 C2 N1 -148.4(5) . . . . ? C11 Sm1 C2 N1 -118.1(5) 11_655 . . . ? N3 Sm1 C2 N1 -118.1(5) 11_655 . . . ? N2 Sm1 C2 N1 -9.4(5) 11_655 . . . ? N2 Sm1 C2 N1 112.6(6) . . . . ? N1 Sm1 C2 N1 71.4(6) 10_557 . . . ? C2 Sm1 C2 N1 105.7(5) 10_557 . . . ? C2 Sm1 C2 N1 46.3(4) 4_656 . . . ? C2 Sm1 C2 N1 -36.8(5) 11_655 . . . ? N3 Sm1 C2 C3 91.8(6) . . . . ? C11 Sm1 C2 C3 122.1(6) 11_655 . . . ? N3 Sm1 C2 C3 122.1(6) 11_655 . . . ? N2 Sm1 C2 C3 -129.2(6) 11_655 . . . ? N2 Sm1 C2 C3 -7.2(6) . . . . ? N1 Sm1 C2 C3 -48.4(7) 10_557 . . . ? N1 Sm1 C2 C3 -119.8(8) . . . . ? C2 Sm1 C2 C3 -14.1(8) 10_557 . . . ? C2 Sm1 C2 C3 -73.5(6) 4_656 . . . ? C2 Sm1 C2 C3 -156.6(5) 11_655 . . . ? C1 C2 C3 C4 117.5(10) . . . . ? N1 C2 C3 C4 -64.4(11) . . . . ? Sm1 C2 C3 C4 20.6(9) . . . . ? C1 C2 C3 C6 -119.2(11) . . . . ? N1 C2 C3 C6 58.9(12) . . . . ? Sm1 C2 C3 C6 144.0(7) . . . . ? C1 C2 C3 C8 0.5(13) . . . . ? N1 C2 C3 C8 178.6(9) . . . . ? Sm1 C2 C3 C8 -96.3(7) . . . . ? C4 N2 C4 C5 2.7(13) 10_557 . . . ? Sm1 N2 C4 C5 -155.0(7) . . . . ? C4 N2 C4 C3 -174.6(5) 10_557 . . . ? Sm1 N2 C4 C3 27.7(12) . . . . ? C2 C3 C4 C5 152.4(9) . . . . ? C6 C3 C4 C5 29.1(14) . . . . ? C8 C3 C4 C5 -92.2(12) . . . . ? C2 C3 C4 N2 -30.9(12) . . . . ? C6 C3 C4 N2 -154.2(9) . . . . ? C8 C3 C4 N2 84.6(10) . . . . ? N2 C4 C5 C5 -1.7(8) . . . 10_557 ? C3 C4 C5 C5 175.3(8) . . . 10_557 ? C4 C3 C6 C7 174.3(9) . . . . ? C2 C3 C6 C7 52.3(12) . . . . ? C8 C3 C6 C7 -65.2(12) . . . . ? C4 C3 C8 C9 64.6(12) . . . . ? C2 C3 C8 C9 -178.1(9) . . . . ? C6 C3 C8 C9 -57.6(12) . . . . ? C11 N3 C12 C15 -161.3(9) 11_655 . . 10_557 ? N3 N3 C12 C15 -161.3(9) 11_655 . . 10_557 ? Sm1 N3 C12 C15 18.7(9) . . . 10_557 ? C11 N3 C12 C15 161.3(9) 11_655 . . . ? N3 N3 C12 C15 161.3(9) 11_655 . . . ? Sm1 N3 C12 C15 -18.7(9) . . . . ? C11 N3 C12 C14 -79.3(12) 11_655 . . . ? N3 N3 C12 C14 -79.3(12) 11_655 . . . ? Sm1 N3 C12 C14 100.7(12) . . . . ? C11 N3 C12 C14 79.3(12) 11_655 . . 10_557 ? N3 N3 C12 C14 79.3(12) 11_655 . . 10_557 ? Sm1 N3 C12 C14 -100.7(12) . . . 10_557 ? C11 N3 C12 C13 -41.0(10) 11_655 . . 10_557 ? N3 N3 C12 C13 -41.0(10) 11_655 . . 10_557 ? Sm1 N3 C12 C13 139.0(10) . . . 10_557 ? C11 N3 C12 C13 41.0(10) 11_655 . . . ? N3 N3 C12 C13 41.0(10) 11_655 . . . ? Sm1 N3 C12 C13 -139.0(10) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 3.143 _refine_diff_density_min -2.250 _refine_diff_density_rms 0.256 # Attachment 'compound_4.cif' data_e:\cncrys~1\smtbucn\ajas12ax _database_code_depnum_ccdc_archive 'CCDC 765858' #TrackingRef 'compound_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C43 H63 N5 Sm), (C6 H6)' _chemical_formula_sum 'C49 H69 N5 Sm' _chemical_formula_weight 878.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Cmc21 _symmetry_space_group_name_Hall 'C 2c -2' _symmetry_Int_Tables_number 36 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, 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' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 17.460(6) _cell_length_b 28.000(15) _cell_length_c 18.760(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9171(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 49950 _cell_measurement_theta_min 1.54 _cell_measurement_theta_max 25.67 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3680 _exptl_absorpt_coefficient_mu 1.318 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.75277 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Synchrotron BM' _diffrn_radiation_monochromator Si<111> _diffrn_measurement_device_type '3-BM1 Australian Synchrotron' _diffrn_measurement_method Rotation _diffrn_detector_area_resol_mean 'ADSC Q210' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49806 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 25.67 _reflns_number_total 7138 _reflns_number_gt 7124 _reflns_threshold_expression >2sigma(I) _computing_data_collection BLU-ICE _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; 'X-SEED (Barbour, 2008) and ORTEPIII (Farrugia, 1998)' ; _computing_publication_material 'WinGX (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All non-hydrogen atoms were refined anisotropically. Hydrogen atoms were placed in calculated positions and refined using a riding model with fixed C-H distances of 0.95 \%A (sp2C-H) and 0.98 \%A (CH3), and Uiso(H) = 1.2Ueq(C) (sp2) and 1.5Ueq(C) (sp3). ; _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^)+(0.0203P)^2^+64.2719P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.359(13) _refine_ls_number_reflns 7138 _refine_ls_number_parameters 527 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0306 _refine_ls_wR_factor_ref 0.0748 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sm1 Sm 0.0000 0.468701(10) 0.437083(16) 0.01660(9) Uani 1 2 d S . . Sm2 Sm 0.0000 0.149252(10) 0.404356(17) 0.01241(8) Uani 1 2 d S . . N1 N 0.0000 0.40892(19) 0.3164(3) 0.0172(12) Uani 1 2 d S . . N2 N 0.1293(2) 0.42493(12) 0.4407(2) 0.0174(8) Uani 1 1 d . . . N3 N 0.0000 0.41892(19) 0.5655(3) 0.0180(13) Uani 1 2 d S . . N4 N 0.0000 0.5619(2) 0.4377(5) 0.0418(17) Uani 1 2 d S . . N5 N 0.0000 0.1952(2) 0.2852(3) 0.0149(13) Uani 1 2 d S . . N6 N 0.13762(19) 0.20382(11) 0.4069(3) 0.0144(7) Uani 1 1 d . . . N7 N 0.0000 0.18863(19) 0.5269(3) 0.0145(12) Uani 1 2 d S . . N8 N 0.0000 0.0562(2) 0.4133(5) 0.0384(18) Uani 1 2 d S . . C1 C 0.0405(3) 0.48149(18) 0.2836(3) 0.0256(12) Uani 1 1 d . . . H1 H 0.0721 0.5080 0.2722 0.031 Uiso 1 1 calc R . . C2 C 0.0660(3) 0.43678(17) 0.3026(2) 0.0189(10) Uani 1 1 d . . . C3 C 0.1464(3) 0.41799(19) 0.3082(3) 0.0228(12) Uani 1 1 d . . . C4 C 0.1636(3) 0.40215(16) 0.3842(2) 0.0183(11) Uani 1 1 d . . . C5 C 0.2182(3) 0.36966(16) 0.4080(3) 0.0265(10) Uani 1 1 d . . . H5 H 0.2495 0.3497 0.3791 0.032 Uiso 1 1 calc R . . C6 C 0.2183(3) 0.37190(18) 0.4830(3) 0.0252(11) Uani 1 1 d . . . H6 H 0.2495 0.3540 0.5147 0.030 Uiso 1 1 calc R . . C7 C 0.1628(3) 0.40612(17) 0.5012(3) 0.0213(11) Uani 1 1 d . . . C8 C 0.1466(3) 0.42745(18) 0.5729(3) 0.0211(11) Uani 1 1 d . . . C9 C 0.0656(3) 0.44709(17) 0.5767(3) 0.0190(10) Uani 1 1 d . . . C10 C 0.0408(3) 0.49262(17) 0.5906(3) 0.0203(10) Uani 1 1 d . . . H10 H 0.0727 0.5196 0.5989 0.024 Uiso 1 1 calc R . . C11 C 0.1593(3) 0.37649(19) 0.2552(3) 0.0250(11) Uani 1 1 d . . . H11A H 0.2138 0.3668 0.2575 0.030 Uiso 1 1 calc R . . H11B H 0.1281 0.3489 0.2706 0.030 Uiso 1 1 calc R . . C12 C 0.1396(4) 0.3880(2) 0.1782(3) 0.0388(15) Uani 1 1 d . . . H12A H 0.1493 0.3599 0.1484 0.058 Uiso 1 1 calc R . . H12B H 0.1714 0.4147 0.1617 0.058 Uiso 1 1 calc R . . H12C H 0.0854 0.3969 0.1749 0.058 Uiso 1 1 calc R . . C13 C 0.2020(4) 0.4598(2) 0.2901(4) 0.0412(16) Uani 1 1 d . . . H13A H 0.1906 0.4700 0.2407 0.049 Uiso 1 1 calc R . . H13B H 0.1883 0.4869 0.3215 0.049 Uiso 1 1 calc R . . C14 C 0.2824(6) 0.4534(4) 0.2950(7) 0.097(3) Uani 1 1 d . . . H14A H 0.3083 0.4832 0.2822 0.145 Uiso 1 1 calc R . . H14B H 0.2984 0.4280 0.2623 0.145 Uiso 1 1 calc R . . H14C H 0.2960 0.4445 0.3440 0.145 Uiso 1 1 calc R . . C15 C 0.2049(3) 0.46853(19) 0.5885(3) 0.0319(14) Uani 1 1 d . . . H15A H 0.1865 0.4863 0.6307 0.038 Uiso 1 1 calc R . . H15B H 0.2545 0.4538 0.6014 0.038 Uiso 1 1 calc R . . C16 C 0.2191(3) 0.5037(2) 0.5301(3) 0.0412(15) Uani 1 1 d . . . H16A H 0.2563 0.5276 0.5463 0.062 Uiso 1 1 calc R . . H16B H 0.1710 0.5195 0.5174 0.062 Uiso 1 1 calc R . . H16C H 0.2395 0.4870 0.4883 0.062 Uiso 1 1 calc R . . C17 C 0.1579(3) 0.3893(2) 0.6331(3) 0.0276(12) Uani 1 1 d . . . H17A H 0.1278 0.3605 0.6206 0.033 Uiso 1 1 calc R . . H17B H 0.2125 0.3799 0.6342 0.033 Uiso 1 1 calc R . . C18 C 0.1346(4) 0.4055(2) 0.7074(3) 0.0380(14) Uani 1 1 d . . . H18A H 0.1430 0.3794 0.7413 0.057 Uiso 1 1 calc R . . H18B H 0.0803 0.4143 0.7074 0.057 Uiso 1 1 calc R . . H18C H 0.1655 0.4332 0.7214 0.057 Uiso 1 1 calc R . . C19 C 0.0000 0.3589(2) 0.3410(4) 0.0179(14) Uani 1 2 d S . . H19A H 0.0000 0.3376 0.2996 0.027 Uiso 1 2 calc SR . . H19C H -0.0458 0.3530 0.3698 0.027 Uiso 0.50 1 calc PR . . H19B H 0.0458 0.3530 0.3698 0.027 Uiso 0.50 1 calc PR . . C20 C 0.0000 0.3674(2) 0.5502(4) 0.0218(16) Uani 1 2 d S . . H20A H 0.0000 0.3495 0.5951 0.033 Uiso 1 2 calc SR . . H20B H 0.0458 0.3592 0.5226 0.033 Uiso 0.50 1 calc PR . . H20C H -0.0458 0.3592 0.5226 0.033 Uiso 0.50 1 calc PR . . C21 C 0.0000 0.6021(3) 0.4338(6) 0.0392(19) Uani 1 2 d S . . C22 C 0.0000 0.6542(2) 0.4369(5) 0.0315(18) Uani 1 2 d S . . C23 C 0.0712(4) 0.6714(3) 0.3961(5) 0.061(2) Uani 1 1 d . . . H23A H 0.0732 0.7063 0.3969 0.091 Uiso 1 1 calc R . . H23B H 0.0686 0.6602 0.3467 0.091 Uiso 1 1 calc R . . H23C H 0.1174 0.6585 0.4189 0.091 Uiso 1 1 calc R . . C24 C 0.0000 0.6715(3) 0.5147(5) 0.050(3) Uani 1 2 d S . . H24A H 0.0000 0.7065 0.5156 0.076 Uiso 1 2 calc SR . . H24B H 0.0458 0.6595 0.5390 0.076 Uiso 0.50 1 calc PR . . H24C H -0.0458 0.6595 0.5390 0.076 Uiso 0.50 1 calc PR . . C25 C 0.0412(3) 0.25759(17) 0.2157(3) 0.0177(10) Uani 1 1 d . . . H25 H 0.0741 0.2792 0.1915 0.021 Uiso 1 1 calc R . . C26 C 0.0627(3) 0.21917(16) 0.2588(3) 0.0140(10) Uani 1 1 d . . . C27 C 0.1420(3) 0.19829(18) 0.2692(3) 0.0152(10) Uani 1 1 d . . . C28 C 0.1489(3) 0.17743(17) 0.3442(3) 0.0143(10) Uani 1 1 d . . . C29 C 0.1649(3) 0.13156(17) 0.3644(3) 0.0193(11) Uani 1 1 d . . . H29 H 0.1745 0.1055 0.3333 0.023 Uiso 1 1 calc R . . C30 C 0.1649(3) 0.12964(15) 0.4403(3) 0.0187(10) Uani 1 1 d . . . H30 H 0.1745 0.1021 0.4685 0.022 Uiso 1 1 calc R . . C31 C 0.1483(3) 0.17506(17) 0.4661(3) 0.0173(11) Uani 1 1 d . . . C32 C 0.1422(3) 0.19179(17) 0.5422(3) 0.0159(11) Uani 1 1 d . . . C33 C 0.0633(3) 0.21164(16) 0.5565(3) 0.0152(10) Uani 1 1 d . . . C34 C 0.0403(3) 0.24844(17) 0.6006(3) 0.0193(10) Uani 1 1 d . . . H34 H 0.0726 0.2697 0.6261 0.023 Uiso 1 1 calc R . . C35 C 0.1501(3) 0.15501(19) 0.2172(3) 0.0177(11) Uani 1 1 d . . . H35A H 0.2009 0.1401 0.2247 0.021 Uiso 1 1 calc R . . H35B H 0.1108 0.1309 0.2295 0.021 Uiso 1 1 calc R . . C36 C 0.1419(3) 0.1678(2) 0.1388(3) 0.0262(12) Uani 1 1 d . . . H36A H 0.1473 0.1389 0.1097 0.039 Uiso 1 1 calc R . . H36B H 0.1817 0.1908 0.1255 0.039 Uiso 1 1 calc R . . H36C H 0.0913 0.1820 0.1305 0.039 Uiso 1 1 calc R . . C37 C 0.2052(3) 0.23592(17) 0.2549(3) 0.0192(11) Uani 1 1 d . . . H37A H 0.1985 0.2486 0.2060 0.023 Uiso 1 1 calc R . . H37B H 0.1981 0.2629 0.2884 0.023 Uiso 1 1 calc R . . C38 C 0.2870(3) 0.21729(19) 0.2624(3) 0.0283(13) Uani 1 1 d . . . H38A H 0.3232 0.2432 0.2528 0.042 Uiso 1 1 calc R . . H38B H 0.2954 0.1913 0.2283 0.042 Uiso 1 1 calc R . . H38C H 0.2948 0.2053 0.3110 0.042 Uiso 1 1 calc R . . C39 C 0.2041(3) 0.23051(18) 0.5581(3) 0.0205(11) Uani 1 1 d . . . H39A H 0.1883 0.2609 0.5355 0.025 Uiso 1 1 calc R . . H39B H 0.2063 0.2359 0.6103 0.025 Uiso 1 1 calc R . . C40 C 0.2846(3) 0.2173(2) 0.5315(3) 0.0296(13) Uani 1 1 d . . . H40A H 0.3204 0.2430 0.5433 0.044 Uiso 1 1 calc R . . H40B H 0.2833 0.2128 0.4797 0.044 Uiso 1 1 calc R . . H40C H 0.3013 0.1876 0.5544 0.044 Uiso 1 1 calc R . . C41 C 0.1547(3) 0.14789(17) 0.5916(3) 0.0216(12) Uani 1 1 d . . . H41A H 0.1190 0.1223 0.5768 0.026 Uiso 1 1 calc R . . H41B H 0.2075 0.1359 0.5844 0.026 Uiso 1 1 calc R . . C42 C 0.1432(3) 0.1573(3) 0.6710(4) 0.0321(12) Uani 1 1 d . . . H42A H 0.1529 0.1279 0.6978 0.048 Uiso 1 1 calc R . . H42B H 0.0904 0.1678 0.6794 0.048 Uiso 1 1 calc R . . H42C H 0.1787 0.1822 0.6867 0.048 Uiso 1 1 calc R . . C43 C 0.1188(3) 0.25508(13) 0.4090(3) 0.0194(9) Uani 1 1 d . . . H43A H 0.0862 0.2617 0.4503 0.029 Uiso 1 1 calc R . . H43B H 0.0916 0.2640 0.3652 0.029 Uiso 1 1 calc R . . H43C H 0.1662 0.2737 0.4126 0.029 Uiso 1 1 calc R . . C44 C 0.0000 0.0153(2) 0.4167(6) 0.038(3) Uani 1 2 d S . . C45 C 0.0000 -0.0364(3) 0.4271(6) 0.042(2) Uani 1 2 d S . . C46 C 0.0710(6) -0.0508(3) 0.4704(6) 0.088(3) Uani 1 1 d . . . H46A H 0.0712 -0.0855 0.4772 0.131 Uiso 1 1 calc R . . H46B H 0.0697 -0.0350 0.5170 0.131 Uiso 1 1 calc R . . H46C H 0.1173 -0.0412 0.4447 0.131 Uiso 1 1 calc R . . C47 C 0.0000 -0.0599(4) 0.3558(6) 0.058(3) Uani 1 2 d S . . H47A H 0.0000 -0.0947 0.3619 0.087 Uiso 1 2 calc SR . . H47B H 0.0458 -0.0503 0.3293 0.087 Uiso 0.50 1 calc PR . . H47C H -0.0458 -0.0503 0.3293 0.087 Uiso 0.50 1 calc PR . . C48 C 0.5000 0.3136(3) 0.4730(5) 0.040(2) Uani 1 2 d S . . H48 H 0.5000 0.3170 0.5234 0.048 Uiso 1 2 calc SR . . C49 C 0.5680(4) 0.3110(2) 0.4356(4) 0.0426(14) Uani 1 1 d . . . H49 H 0.6152 0.3120 0.4608 0.051 Uiso 1 1 calc R . . C50 C 0.5686(4) 0.3071(2) 0.3626(4) 0.0410(16) Uani 1 1 d . . . H50 H 0.6158 0.3065 0.3374 0.049 Uiso 1 1 calc R . . C51 C 0.5000 0.3040(3) 0.3262(5) 0.037(2) Uani 1 2 d S . . H51 H 0.5000 0.2997 0.2759 0.044 Uiso 1 2 calc SR . . C52 C 0.0000 0.0447(3) 0.6420(6) 0.052(3) Uani 1 2 d S . . H52 H 0.0000 0.0766 0.6247 0.062 Uiso 1 2 calc SR . . C53 C 0.0679(5) 0.0223(2) 0.6541(4) 0.0509(18) Uani 1 1 d . . . H53 H 0.1148 0.0386 0.6456 0.061 Uiso 1 1 calc R . . C54 C 0.0686(4) -0.0249(2) 0.6792(4) 0.0533(19) Uani 1 1 d . . . H54 H 0.1158 -0.0408 0.6872 0.064 Uiso 1 1 calc R . . C55 C 0.0000 -0.0480(3) 0.6922(6) 0.050(3) Uani 1 2 d S . . H55 H 0.0000 -0.0798 0.7100 0.060 Uiso 1 2 calc SR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Sm1 0.02295(17) 0.01327(16) 0.01358(17) 0.00077(14) 0.000 0.000 Sm2 0.01596(15) 0.01250(15) 0.00879(16) -0.00051(14) 0.000 0.000 N1 0.020(3) 0.017(3) 0.015(3) 0.001(2) 0.000 0.000 N2 0.0174(18) 0.0180(17) 0.017(2) -0.0023(18) -0.0006(18) -0.0014(14) N3 0.024(3) 0.010(3) 0.020(3) -0.004(2) 0.000 0.000 N4 0.056(4) 0.017(3) 0.053(5) -0.017(4) 0.000 0.000 N5 0.024(3) 0.017(3) 0.004(3) 0.003(2) 0.000 0.000 N6 0.0193(17) 0.0132(16) 0.0107(18) -0.0013(17) -0.0014(19) 0.0002(13) N7 0.014(3) 0.016(3) 0.013(3) 0.004(2) 0.000 0.000 N8 0.039(4) 0.037(4) 0.040(5) 0.007(3) 0.000 0.000 C1 0.035(3) 0.021(3) 0.021(3) 0.004(2) 0.007(2) -0.009(2) C2 0.028(3) 0.021(2) 0.007(3) 0.0015(18) 0.003(2) -0.006(2) C3 0.025(3) 0.023(3) 0.021(3) 0.001(2) 0.003(2) -0.006(2) C4 0.026(2) 0.019(2) 0.010(3) -0.0026(17) 0.0006(17) -0.0062(19) C5 0.031(2) 0.027(2) 0.022(3) -0.008(2) 0.004(2) 0.0072(19) C6 0.030(3) 0.025(2) 0.021(3) -0.003(2) -0.001(2) 0.007(2) C7 0.017(2) 0.019(2) 0.027(3) -0.001(2) -0.002(2) 0.002(2) C8 0.022(3) 0.021(2) 0.021(3) -0.002(2) -0.003(2) 0.001(2) C9 0.018(2) 0.020(2) 0.019(3) 0.0014(19) -0.0038(19) -0.0020(19) C10 0.029(3) 0.021(3) 0.011(3) -0.0022(18) 0.002(2) -0.004(2) C11 0.022(3) 0.038(3) 0.015(3) -0.005(2) 0.007(2) -0.001(2) C12 0.032(3) 0.060(4) 0.025(3) -0.008(3) 0.008(2) 0.008(3) C13 0.036(4) 0.050(4) 0.037(4) 0.014(3) -0.007(3) -0.025(3) C14 0.073(6) 0.085(7) 0.132(10) 0.017(6) 0.034(6) -0.003(5) C15 0.026(3) 0.033(3) 0.036(4) -0.013(2) -0.008(3) 0.001(2) C16 0.034(3) 0.045(3) 0.045(4) -0.014(3) 0.011(3) -0.017(3) C17 0.032(3) 0.033(3) 0.018(3) 0.001(2) -0.008(2) 0.013(2) C18 0.053(4) 0.043(4) 0.018(3) 0.004(2) 0.000(3) 0.017(3) C19 0.023(4) 0.019(4) 0.012(4) 0.002(3) 0.000 0.000 C20 0.030(4) 0.012(3) 0.023(4) 0.000(3) 0.000 0.000 C21 0.050(5) 0.035(5) 0.032(5) 0.004(4) 0.000 0.000 C22 0.046(5) 0.021(3) 0.028(4) -0.003(4) 0.000 0.000 C23 0.073(5) 0.057(4) 0.053(5) -0.006(4) 0.014(4) -0.021(4) C24 0.069(7) 0.041(5) 0.042(6) -0.009(4) 0.000 0.000 C25 0.026(3) 0.017(2) 0.010(3) -0.0012(18) -0.001(2) -0.002(2) C26 0.012(2) 0.017(2) 0.013(3) -0.0033(18) 0.0025(18) -0.0012(18) C27 0.017(3) 0.021(2) 0.008(3) -0.0016(19) 0.0009(19) 0.003(2) C28 0.011(2) 0.021(2) 0.011(3) -0.0010(19) 0.0009(18) 0.001(2) C29 0.022(3) 0.021(2) 0.014(3) -0.007(2) 0.003(2) 0.003(2) C30 0.021(2) 0.016(2) 0.018(3) 0.000(2) 0.003(2) 0.0013(18) C31 0.016(2) 0.017(2) 0.018(3) 0.0000(19) 0.000(2) 0.002(2) C32 0.017(3) 0.016(3) 0.015(3) 0.000(2) -0.002(2) -0.0020(19) C33 0.021(2) 0.017(2) 0.008(3) 0.0006(17) -0.0031(18) -0.0027(19) C34 0.023(3) 0.019(2) 0.017(3) -0.0002(19) -0.002(2) -0.002(2) C35 0.016(3) 0.024(3) 0.013(3) -0.002(2) -0.001(2) 0.000(2) C36 0.036(3) 0.031(3) 0.012(3) -0.009(2) 0.001(2) 0.004(2) C37 0.019(3) 0.021(2) 0.017(3) 0.000(2) 0.005(2) -0.006(2) C38 0.024(3) 0.024(3) 0.036(4) 0.006(2) -0.002(2) -0.005(2) C39 0.023(3) 0.024(3) 0.014(3) -0.0037(19) -0.001(2) -0.001(2) C40 0.016(3) 0.041(3) 0.032(3) -0.001(2) -0.003(2) -0.005(2) C41 0.026(3) 0.021(3) 0.017(3) 0.0053(19) -0.010(2) 0.002(2) C42 0.039(3) 0.038(3) 0.020(3) 0.010(2) -0.004(3) 0.008(3) C43 0.027(2) 0.0137(19) 0.017(2) 0.000(2) -0.004(2) 0.0010(17) C44 0.033(4) 0.016(4) 0.065(8) 0.007(4) 0.000 0.000 C45 0.067(6) 0.025(4) 0.035(7) 0.002(3) 0.000 0.000 C46 0.112(8) 0.043(4) 0.108(8) -0.005(4) -0.049(6) 0.026(5) C47 0.058(7) 0.055(6) 0.061(8) 0.003(5) 0.000 0.000 C48 0.066(7) 0.035(5) 0.020(4) 0.009(4) 0.000 0.000 C49 0.054(4) 0.037(3) 0.037(4) -0.004(3) -0.011(3) 0.012(3) C50 0.042(4) 0.041(4) 0.039(4) -0.003(3) 0.010(3) 0.008(3) C51 0.045(5) 0.041(5) 0.025(5) -0.005(4) 0.000 0.000 C52 0.067(7) 0.030(5) 0.058(7) 0.008(4) 0.000 0.000 C53 0.056(5) 0.043(4) 0.054(5) 0.009(3) 0.006(3) -0.008(3) C54 0.049(4) 0.036(4) 0.075(6) 0.010(3) -0.002(4) 0.002(3) C55 0.044(6) 0.025(5) 0.082(8) 0.017(4) 0.000 0.000 _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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 0.0000 (0.0000) x + 8.0152 (0.1036) y + 17.9749 (0.0228) z = 8.9519 (0.0401) * 0.0138 (0.0040) N1 * 0.0043 (0.0013) C1 * -0.0112 (0.0033) C2 * 0.0043 (0.0013) C1_$1 * -0.0112 (0.0033) C2_$1 0.0539 (0.0127) C19 -0.0612 (0.0070) C3 Rms deviation of fitted atoms = 0.0098 0.0000 (0.0000) x + 27.9602 (0.0152) y - 0.9993 (0.0298) z = 11.3791 (0.0160) Angle to previous plane (with approximate esd) = 76.42 ( 0.24 ) * 0.0000 (0.0000) C3 * 0.0000 (0.0000) C3_$1 * 0.0000 (0.0000) C8 * 0.0000 (0.0000) C8_$1 1.2891 (0.0034) Sm1 Rms deviation of fitted atoms = 0.0000 12.1994 (0.0274) x + 20.0114 (0.0431) y - 0.6016 (0.0539) z = 9.8137 (0.0281) Angle to previous plane (with approximate esd) = 44.33 ( 0.12 ) * 0.0017 (0.0025) N2 * -0.0010 (0.0028) C4 * 0.0000 (0.0032) C5 * 0.0011 (0.0033) C6 * -0.0017 (0.0030) C7 0.1513 (0.0088) C3 0.1835 (0.0092) C8 Rms deviation of fitted atoms = 0.0013 0.0000 (0.0000) x - 6.0733 (0.0974) y + 18.3134 (0.0175) z = 7.8306 (0.0532) Angle to previous plane (with approximate esd) = 79.26 ( 0.22 ) * -0.0184 (0.0042) N3 * 0.0150 (0.0034) C9 * -0.0058 (0.0013) C10 * -0.0058 (0.0013) C10_$1 * 0.0150 (0.0034) C9_$1 0.0140 (0.0124) C20 0.0648 (0.0069) C8 Rms deviation of fitted atoms = 0.0131 0.0000 (0.0000) x + 27.9602 (0.0152) y - 0.9993 (0.0298) z = 11.3791 (0.0160) Angle to previous plane (with approximate esd) = 74.42 ( 0.23 ) * 0.0000 (0.0000) C3 * 0.0000 (0.0000) C3_$1 * 0.0000 (0.0000) C8 * 0.0000 (0.0000) C8_$1 1.2891 (0.0034) Sm1 Rms deviation of fitted atoms = 0.0000 - 0.0000 (0.0001) x + 28.0000 (0.0150) y - 0.0333 (0.1034) z = 18.7846 (0.0468) Angle to previous plane (with approximate esd) = 2.95 ( 0.05 ) * 0.0000 (0.0000) C23 * 0.0000 (0.0000) C24 * 0.0000 (0.0000) C23_$1 Rms deviation of fitted atoms = 0.0000 0.0000 (0.0000) x + 16.7658 (0.0731) y + 15.0251 (0.0372) z = 7.5608 (0.0088) Angle to previous plane (with approximate esd) = 53.32 ( 0.35 ) * -0.0021 (0.0041) N5 * -0.0007 (0.0013) C25 * 0.0017 (0.0033) C26 * -0.0007 (0.0013) C25_$1 * 0.0017 (0.0033) C26_$1 -0.1917 (0.0063) C27 Rms deviation of fitted atoms = 0.0015 - 0.0000 (0.0000) x + 27.9823 (0.0151) y + 0.6660 (0.0278) z = 5.7279 (0.0120) Angle to previous plane (with approximate esd) = 51.18 ( 0.20 ) * 0.0000 (0.0000) C27 * 0.0000 (0.0000) C27_$1 * 0.0000 (0.0000) C32 * 0.0000 (0.0000) C32_$1 -1.2822 (0.0032) Sm2 Rms deviation of fitted atoms = 0.0000 17.0177 (0.0120) x + 6.2553 (0.0543) y + 0.1992 (0.0545) z = 3.7054 (0.0235) Angle to previous plane (with approximate esd) = 77.08 ( 0.12 ) * -0.0075 (0.0023) N6 * 0.0066 (0.0027) C28 * -0.0032 (0.0033) C29 * -0.0014 (0.0032) C30 * 0.0055 (0.0027) C31 0.0044 (0.0094) C27 0.0224 (0.0093) C32 -0.0062 (0.0069) C43 Rms deviation of fitted atoms = 0.0054 - 0.0000 (0.0001) x - 17.7423 (0.0727) y + 14.5131 (0.0403) z = 4.3123 (0.0381) Angle to previous plane (with approximate esd) = 82.34 ( 0.16 ) * -0.0119 (0.0039) N7 * 0.0098 (0.0032) C33 * -0.0038 (0.0013) C34 * -0.0038 (0.0013) C34_$1 * 0.0098 (0.0032) C33_$1 0.1539 (0.0064) C32 Rms deviation of fitted atoms = 0.0085 - 0.0000 (0.0000) x + 27.9823 (0.0151) y + 0.6660 (0.0278) z = 5.7279 (0.0120) Angle to previous plane (with approximate esd) = 52.71 ( 0.20 ) * 0.0000 (0.0000) C27 * 0.0000 (0.0000) C27_$1 * 0.0000 (0.0000) C32 * 0.0000 (0.0000) C32_$1 -1.2822 (0.0032) Sm2 Rms deviation of fitted atoms = 0.0000 0.0000 (0.0002) x - 27.8060 (0.0257) y + 2.2047 (0.1182) z = 2.4509 (0.0503) Angle to previous plane (with approximate esd) = 8.78 ( 0.11 ) * 0.0000 (0.0000) C46 * 0.0000 (0.0000) C47 * 0.0000 (0.0000) C46_$1 Rms deviation of fitted atoms = 0.0000 ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sm1 N2 2.569(4) . ? Sm1 N2 2.569(4) 3 ? Sm1 N4 2.609(6) . ? Sm1 N3 2.783(6) . ? Sm1 N1 2.815(6) . ? Sm1 C2 2.914(5) 3 ? Sm1 C2 2.914(5) . ? Sm1 C9 2.921(5) . ? Sm1 C9 2.921(5) 3 ? Sm1 C1 2.987(5) 3 ? Sm1 C1 2.987(5) . ? Sm1 C10 3.042(5) . ? Sm2 N7 2.550(6) . ? Sm2 N5 2.579(5) . ? Sm2 N8 2.612(7) . ? Sm2 N6 2.848(3) 3 ? Sm2 N6 2.848(3) . ? Sm2 C31 2.927(5) 3 ? Sm2 C31 2.927(5) . ? Sm2 C28 2.942(5) . ? Sm2 C28 2.942(5) 3 ? Sm2 C30 3.007(5) 3 ? Sm2 C30 3.007(5) . ? Sm2 C29 3.016(5) . ? N1 C2 1.416(6) . ? N1 C2 1.416(6) 3 ? N1 C19 1.473(9) . ? N2 C4 1.375(6) . ? N2 C7 1.382(7) . ? N3 C9 1.406(6) . ? N3 C9 1.406(6) 3 ? N3 C20 1.471(8) . ? N4 C21 1.129(10) . ? N5 C26 1.377(6) . ? N5 C26 1.377(6) 3 ? N6 C31 1.385(7) . ? N6 C28 1.404(7) . ? N6 C43 1.473(5) . ? N7 C33 1.395(6) . ? N7 C33 1.395(6) 3 ? N8 C44 1.146(10) . ? C1 C2 1.376(7) . ? C1 C1 1.414(11) 3 ? C1 H1 0.9500 . ? C2 C3 1.502(8) . ? C3 C4 1.522(7) . ? C3 C11 1.546(7) . ? C3 C13 1.558(7) . ? C4 C5 1.391(7) . ? C5 C6 1.409(8) . ? C5 H5 0.9500 . ? C6 C7 1.405(7) . ? C6 H6 0.9500 . ? C7 C8 1.499(8) . ? C8 C9 1.519(7) . ? C8 C15 1.564(7) . ? C8 C17 1.567(7) . ? C9 C10 1.371(7) . ? C10 C10 1.425(10) 3 ? C10 H10 0.9500 . ? C11 C12 1.519(8) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.419(12) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.493(9) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.521(8) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19C 0.9800 . ? C19 H19B 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.458(10) . ? C22 C23 1.537(9) 3 ? C22 C23 1.537(9) . ? C22 C24 1.538(14) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.396(7) . ? C25 C25 1.439(10) 3 ? C25 H25 0.9500 . ? C26 C27 1.514(7) . ? C27 C28 1.528(7) . ? C27 C37 1.550(7) . ? C27 C35 1.561(7) . ? C28 C29 1.368(7) . ? C29 C30 1.425(7) . ? C29 H29 0.9500 . ? C30 C31 1.391(7) . ? C30 H30 0.9500 . ? C31 C32 1.506(8) . ? C32 C33 1.509(7) . ? C32 C41 1.555(7) . ? C32 C39 1.560(7) . ? C33 C34 1.381(7) . ? C34 C34 1.406(10) 3 ? C34 H34 0.9500 . ? C35 C36 1.522(7) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 C38 1.526(7) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 C40 1.537(7) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 C42 1.524(9) . ? C41 H41A 0.9900 . ? C41 H41B 0.9900 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 0.9800 . ? C44 C45 1.461(10) . ? C45 C47 1.491(15) . ? C45 C46 1.536(10) . ? C45 C46 1.536(10) 3 ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 H47A 0.9800 . ? C47 H47B 0.9800 . ? C47 H47C 0.9800 . ? C48 C49 1.382(8) . ? C48 C49 1.382(8) 3_655 ? C48 H48 0.9500 . ? C49 C50 1.374(10) . ? C49 H49 0.9500 . ? C50 C51 1.383(8) . ? C50 H50 0.9500 . ? C51 C50 1.383(8) 3_655 ? C51 H51 0.9500 . ? C52 C53 1.361(9) . ? C52 C53 1.361(9) 3 ? C52 H52 0.9500 . ? C53 C54 1.403(8) . ? C53 H53 0.9500 . ? C54 C55 1.383(9) . ? C54 H54 0.9500 . ? C55 C54 1.383(9) 3 ? C55 H55 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 Sm1 N2 122.92(15) . 3 ? N2 Sm1 N4 118.48(8) . . ? N2 Sm1 N4 118.48(8) 3 . ? N2 Sm1 N3 74.84(11) . . ? N2 Sm1 N3 74.84(11) 3 . ? N4 Sm1 N3 119.8(2) . . ? N2 Sm1 N1 74.78(11) . . ? N2 Sm1 N1 74.78(11) 3 . ? N4 Sm1 N1 126.7(2) . . ? N3 Sm1 N1 113.46(16) . . ? N2 Sm1 C2 102.94(14) . 3 ? N2 Sm1 C2 61.89(14) 3 3 ? N4 Sm1 C2 108.1(2) . 3 ? N3 Sm1 C2 126.56(14) . 3 ? N1 Sm1 C2 28.55(11) . 3 ? N2 Sm1 C2 61.89(14) . . ? N2 Sm1 C2 102.94(14) 3 . ? N4 Sm1 C2 108.1(2) . . ? N3 Sm1 C2 126.56(14) . . ? N1 Sm1 C2 28.55(11) . . ? C2 Sm1 C2 46.6(2) 3 . ? N2 Sm1 C9 62.19(14) . . ? N2 Sm1 C9 102.82(14) 3 . ? N4 Sm1 C9 101.7(2) . . ? N3 Sm1 C9 28.40(11) . . ? N1 Sm1 C9 126.70(14) . . ? C2 Sm1 C9 150.17(12) 3 . ? C2 Sm1 C9 123.88(13) . . ? N2 Sm1 C9 102.82(14) . 3 ? N2 Sm1 C9 62.19(14) 3 3 ? N4 Sm1 C9 101.7(2) . 3 ? N3 Sm1 C9 28.40(11) . 3 ? N1 Sm1 C9 126.70(14) . 3 ? C2 Sm1 C9 123.88(13) 3 3 ? C2 Sm1 C9 150.17(12) . 3 ? C9 Sm1 C9 46.1(2) . 3 ? N2 Sm1 C1 106.88(15) . 3 ? N2 Sm1 C1 82.80(15) 3 3 ? N4 Sm1 C1 83.3(2) . 3 ? N3 Sm1 C1 153.46(14) . 3 ? N1 Sm1 C1 45.26(15) . 3 ? C2 Sm1 C1 26.94(14) 3 3 ? C2 Sm1 C1 45.23(14) . 3 ? C9 Sm1 C1 169.07(14) . 3 ? C9 Sm1 C1 142.79(15) 3 3 ? N2 Sm1 C1 82.80(15) . . ? N2 Sm1 C1 106.88(15) 3 . ? N4 Sm1 C1 83.3(2) . . ? N3 Sm1 C1 153.46(14) . . ? N1 Sm1 C1 45.26(15) . . ? C2 Sm1 C1 45.23(14) 3 . ? C2 Sm1 C1 26.94(14) . . ? C9 Sm1 C1 142.79(15) . . ? C9 Sm1 C1 169.07(14) 3 . ? C1 Sm1 C1 27.4(2) 3 . ? N2 Sm1 C10 82.78(14) . . ? N2 Sm1 C10 106.62(14) 3 . ? N4 Sm1 C10 77.0(2) . . ? N3 Sm1 C10 44.82(15) . . ? N1 Sm1 C10 153.16(14) . . ? C2 Sm1 C10 168.50(14) 3 . ? C2 Sm1 C10 142.62(14) . . ? C9 Sm1 C10 26.49(14) . . ? C9 Sm1 C10 44.65(14) 3 . ? C1 Sm1 C10 160.39(13) 3 . ? C1 Sm1 C10 146.22(13) . . ? N7 Sm2 N5 124.44(16) . . ? N7 Sm2 N8 111.9(2) . . ? N5 Sm2 N8 123.6(2) . . ? N7 Sm2 N6 75.69(11) . 3 ? N5 Sm2 N6 75.34(11) . 3 ? N8 Sm2 N6 122.29(7) . 3 ? N7 Sm2 N6 75.69(11) . . ? N5 Sm2 N6 75.34(11) . . ? N8 Sm2 N6 122.30(7) . . ? N6 Sm2 N6 115.07(14) 3 . ? N7 Sm2 C31 62.37(10) . 3 ? N5 Sm2 C31 102.70(11) . 3 ? N8 Sm2 C31 102.76(13) . 3 ? N6 Sm2 C31 27.70(14) 3 3 ? N6 Sm2 C31 127.38(13) . 3 ? N7 Sm2 C31 62.37(10) . . ? N5 Sm2 C31 102.70(11) . . ? N8 Sm2 C31 102.76(13) . . ? N6 Sm2 C31 127.38(13) 3 . ? N6 Sm2 C31 27.70(14) . . ? C31 Sm2 C31 124.4(2) 3 . ? N7 Sm2 C28 103.30(11) . . ? N5 Sm2 C28 62.20(9) . . ? N8 Sm2 C28 107.00(12) . . ? N6 Sm2 C28 127.46(12) 3 . ? N6 Sm2 C28 28.00(13) . . ? C31 Sm2 C28 150.14(11) 3 . ? C31 Sm2 C28 45.91(12) . . ? N7 Sm2 C28 103.30(11) . 3 ? N5 Sm2 C28 62.20(9) . 3 ? N8 Sm2 C28 107.00(12) . 3 ? N6 Sm2 C28 28.00(13) 3 3 ? N6 Sm2 C28 127.46(12) . 3 ? C31 Sm2 C28 45.91(12) 3 3 ? C31 Sm2 C28 150.14(11) . 3 ? C28 Sm2 C28 124.17(19) . 3 ? N7 Sm2 C30 82.91(11) . 3 ? N5 Sm2 C30 106.60(10) . 3 ? N8 Sm2 C30 78.65(9) . 3 ? N6 Sm2 C30 44.49(11) 3 3 ? N6 Sm2 C30 154.40(12) . 3 ? C31 Sm2 C30 27.08(13) 3 3 ? C31 Sm2 C30 143.40(15) . 3 ? C28 Sm2 C30 168.80(14) . 3 ? C28 Sm2 C30 44.71(14) 3 3 ? N7 Sm2 C30 82.91(11) . . ? N5 Sm2 C30 106.60(10) . . ? N8 Sm2 C30 78.65(9) . . ? N6 Sm2 C30 154.40(12) 3 . ? N6 Sm2 C30 44.49(11) . . ? C31 Sm2 C30 143.40(15) 3 . ? C31 Sm2 C30 27.08(13) . . ? C28 Sm2 C30 44.71(14) . . ? C28 Sm2 C30 168.80(14) 3 . ? C30 Sm2 C30 146.3(2) 3 . ? N7 Sm2 C29 107.15(9) . . ? N5 Sm2 C29 82.35(10) . . ? N8 Sm2 C29 81.50(11) . . ? N6 Sm2 C29 153.87(12) 3 . ? N6 Sm2 C29 44.50(12) . . ? C31 Sm2 C29 169.48(14) 3 . ? C31 Sm2 C29 45.13(14) . . ? C28 Sm2 C29 26.51(13) . . ? C28 Sm2 C29 142.40(13) 3 . ? C30 Sm2 C29 159.98(11) 3 . ? C30 Sm2 C29 27.37(13) . . ? C2 N1 C2 109.0(5) . 3 ? C2 N1 C19 125.5(3) . . ? C2 N1 C19 125.5(3) 3 . ? C2 N1 Sm1 79.6(3) . . ? C2 N1 Sm1 79.6(3) 3 . ? C19 N1 Sm1 108.3(4) . . ? C4 N2 C7 105.8(3) . . ? C4 N2 Sm1 125.8(3) . . ? C7 N2 Sm1 125.2(3) . . ? C9 N3 C9 109.0(5) . 3 ? C9 N3 C20 125.4(3) . . ? C9 N3 C20 125.4(3) 3 . ? C9 N3 Sm1 81.3(3) . . ? C9 N3 Sm1 81.3(3) 3 . ? C20 N3 Sm1 108.8(4) . . ? C21 N4 Sm1 176.1(9) . . ? C26 N5 C26 105.4(5) . 3 ? C26 N5 Sm2 123.7(3) . . ? C26 N5 Sm2 123.7(3) 3 . ? C31 N6 C28 110.4(3) . . ? C31 N6 C43 125.2(4) . . ? C28 N6 C43 124.5(4) . . ? C31 N6 Sm2 79.3(2) . . ? C28 N6 Sm2 79.7(2) . . ? C43 N6 Sm2 109.6(2) . . ? C33 N7 C33 104.9(6) . 3 ? C33 N7 Sm2 124.0(3) . . ? C33 N7 Sm2 124.0(3) 3 . ? C44 N8 Sm2 179.5(9) . . ? C2 C1 C1 108.9(3) . 3 ? C2 C1 Sm1 73.6(3) . . ? C1 C1 Sm1 76.31(11) 3 . ? C2 C1 H1 125.5 . . ? C1 C1 H1 125.5 3 . ? Sm1 C1 H1 116.5 . . ? C1 C2 N1 106.6(4) . . ? C1 C2 C3 129.7(4) . . ? N1 C2 C3 123.7(4) . . ? C1 C2 Sm1 79.5(3) . . ? N1 C2 Sm1 71.8(3) . . ? C3 C2 Sm1 114.6(3) . . ? C2 C3 C4 110.6(4) . . ? C2 C3 C11 110.8(4) . . ? C4 C3 C11 110.8(4) . . ? C2 C3 C13 107.7(5) . . ? C4 C3 C13 107.5(4) . . ? C11 C3 C13 109.4(5) . . ? N2 C4 C5 110.8(4) . . ? N2 C4 C3 120.0(4) . . ? C5 C4 C3 128.8(5) . . ? C4 C5 C6 107.0(5) . . ? C4 C5 H5 126.5 . . ? C6 C5 H5 126.5 . . ? C7 C6 C5 105.8(5) . . ? C7 C6 H6 127.1 . . ? C5 C6 H6 127.1 . . ? N2 C7 C6 110.6(5) . . ? N2 C7 C8 120.3(4) . . ? C6 C7 C8 128.4(5) . . ? C7 C8 C9 111.3(4) . . ? C7 C8 C15 109.7(4) . . ? C9 C8 C15 109.4(4) . . ? C7 C8 C17 110.6(4) . . ? C9 C8 C17 109.3(4) . . ? C15 C8 C17 106.5(4) . . ? C10 C9 N3 107.1(4) . . ? C10 C9 C8 129.7(4) . . ? N3 C9 C8 123.2(4) . . ? C10 C9 Sm1 81.7(3) . . ? N3 C9 Sm1 70.3(3) . . ? C8 C9 Sm1 113.4(3) . . ? C9 C10 C10 108.4(3) . 3 ? C9 C10 Sm1 71.8(3) . . ? C10 C10 Sm1 76.45(10) 3 . ? C9 C10 H10 125.8 . . ? C10 C10 H10 125.8 3 . ? Sm1 C10 H10 117.8 . . ? C12 C11 C3 114.8(5) . . ? C12 C11 H11A 108.6 . . ? C3 C11 H11A 108.6 . . ? C12 C11 H11B 108.6 . . ? C3 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C3 120.5(7) . . ? C14 C13 H13A 107.2 . . ? C3 C13 H13A 107.2 . . ? C14 C13 H13B 107.2 . . ? C3 C13 H13B 107.2 . . ? H13A C13 H13B 106.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C8 117.1(5) . . ? C16 C15 H15A 108.0 . . ? C8 C15 H15A 108.0 . . ? C16 C15 H15B 108.0 . . ? C8 C15 H15B 108.0 . . ? H15A C15 H15B 107.3 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C8 115.1(4) . . ? C18 C17 H17A 108.5 . . ? C8 C17 H17A 108.5 . . ? C18 C17 H17B 108.5 . . ? C8 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 H19A 109.5 . . ? N1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? N1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? H19C C19 H19B 109.5 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N4 C21 C22 174.1(12) . . ? C21 C22 C23 107.1(5) . 3 ? C21 C22 C23 107.1(5) . . ? C23 C22 C23 108.0(9) 3 . ? C21 C22 C24 110.6(8) . . ? C23 C22 C24 111.9(5) 3 . ? C23 C22 C24 111.9(5) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C25 105.6(3) . 3 ? C26 C25 H25 127.2 . . ? C25 C25 H25 127.2 3 . ? N5 C26 C25 111.7(4) . . ? N5 C26 C27 119.5(4) . . ? C25 C26 C27 128.2(4) . . ? C26 C27 C28 109.8(4) . . ? C26 C27 C37 111.5(4) . . ? C28 C27 C37 111.3(4) . . ? C26 C27 C35 107.6(4) . . ? C28 C27 C35 105.7(4) . . ? C37 C27 C35 110.8(4) . . ? C29 C28 N6 106.8(4) . . ? C29 C28 C27 129.1(5) . . ? N6 C28 C27 124.0(4) . . ? C29 C28 Sm2 79.8(3) . . ? N6 C28 Sm2 72.3(2) . . ? C27 C28 Sm2 112.7(3) . . ? C28 C29 C30 108.2(4) . . ? C28 C29 Sm2 73.7(3) . . ? C30 C29 Sm2 76.0(3) . . ? C28 C29 H29 125.9 . . ? C30 C29 H29 125.9 . . ? Sm2 C29 H29 116.5 . . ? C31 C30 C29 108.2(5) . . ? C31 C30 Sm2 73.3(3) . . ? C29 C30 Sm2 76.7(3) . . ? C31 C30 H30 125.9 . . ? C29 C30 H30 125.9 . . ? Sm2 C30 H30 116.3 . . ? N6 C31 C30 106.3(4) . . ? N6 C31 C32 124.8(4) . . ? C30 C31 C32 128.9(5) . . ? N6 C31 Sm2 73.0(2) . . ? C30 C31 Sm2 79.7(3) . . ? C32 C31 Sm2 113.0(3) . . ? C31 C32 C33 110.3(4) . . ? C31 C32 C41 108.0(4) . . ? C33 C32 C41 108.2(4) . . ? C31 C32 C39 110.4(4) . . ? C33 C32 C39 110.0(4) . . ? C41 C32 C39 109.7(4) . . ? C34 C33 N7 110.6(4) . . ? C34 C33 C32 130.4(4) . . ? N7 C33 C32 118.8(4) . . ? C33 C34 C34 107.0(3) . 3 ? C33 C34 H34 126.5 . . ? C34 C34 H34 126.5 3 . ? C36 C35 C27 114.3(4) . . ? C36 C35 H35A 108.7 . . ? C27 C35 H35A 108.7 . . ? C36 C35 H35B 108.7 . . ? C27 C35 H35B 108.7 . . ? H35A C35 H35B 107.6 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C38 C37 C27 114.7(4) . . ? C38 C37 H37A 108.6 . . ? C27 C37 H37A 108.6 . . ? C38 C37 H37B 108.6 . . ? C27 C37 H37B 108.6 . . ? H37A C37 H37B 107.6 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C40 C39 C32 113.8(4) . . ? C40 C39 H39A 108.8 . . ? C32 C39 H39A 108.8 . . ? C40 C39 H39B 108.8 . . ? C32 C39 H39B 108.8 . . ? H39A C39 H39B 107.7 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C42 C41 C32 115.3(5) . . ? C42 C41 H41A 108.5 . . ? C32 C41 H41A 108.5 . . ? C42 C41 H41B 108.5 . . ? C32 C41 H41B 108.5 . . ? H41A C41 H41B 107.5 . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? N6 C43 H43A 109.5 . . ? N6 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? N6 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? N8 C44 C45 175.5(11) . . ? C44 C45 C47 108.6(9) . . ? C44 C45 C46 109.4(5) . . ? C47 C45 C46 111.0(6) . . ? C44 C45 C46 109.4(5) . 3 ? C47 C45 C46 111.0(6) . 3 ? C46 C45 C46 107.6(11) . 3 ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C45 C47 H47A 109.5 . . ? C45 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C45 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C49 C48 C49 118.6(9) . 3_655 ? C49 C48 H48 120.7 . . ? C49 C48 H48 120.7 3_655 . ? C50 C49 C48 121.1(7) . . ? C50 C49 H49 119.4 . . ? C48 C49 H49 119.4 . . ? C49 C50 C51 119.4(7) . . ? C49 C50 H50 120.3 . . ? C51 C50 H50 120.3 . . ? C50 C51 C50 120.2(9) . 3_655 ? C50 C51 H51 119.9 . . ? C50 C51 H51 119.9 3_655 . ? C53 C52 C53 121.3(9) . 3 ? C53 C52 H52 119.3 . . ? C53 C52 H52 119.3 3 . ? C52 C53 C54 119.8(8) . . ? C52 C53 H53 120.1 . . ? C54 C53 H53 120.1 . . ? C55 C54 C53 119.5(8) . . ? C55 C54 H54 120.2 . . ? C53 C54 H54 120.2 . . ? C54 C55 C54 120.0(9) . 3 ? C54 C55 H55 120.0 . . ? C54 C55 H55 120.0 3 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Sm1 N1 C2 -58.6(3) . . . . ? N2 Sm1 N1 C2 170.3(3) 3 . . . ? N4 Sm1 N1 C2 55.9(3) . . . . ? N3 Sm1 N1 C2 -124.1(3) . . . . ? C2 Sm1 N1 C2 111.8(5) 3 . . . ? C9 Sm1 N1 C2 -94.9(3) . . . . ? C9 Sm1 N1 C2 -153.4(3) 3 . . . ? C1 Sm1 N1 C2 75.3(3) 3 . . . ? C1 Sm1 N1 C2 36.4(3) . . . . ? C10 Sm1 N1 C2 -92.9(4) . . . . ? N2 Sm1 N1 C2 -170.3(3) . . . 3 ? N2 Sm1 N1 C2 58.6(3) 3 . . 3 ? N4 Sm1 N1 C2 -55.9(3) . . . 3 ? N3 Sm1 N1 C2 124.1(3) . . . 3 ? C2 Sm1 N1 C2 -111.8(5) . . . 3 ? C9 Sm1 N1 C2 153.4(3) . . . 3 ? C9 Sm1 N1 C2 94.9(3) 3 . . 3 ? C1 Sm1 N1 C2 -36.4(3) 3 . . 3 ? C1 Sm1 N1 C2 -75.3(3) . . . 3 ? C10 Sm1 N1 C2 155.4(3) . . . 3 ? N2 Sm1 N1 C19 65.57(9) . . . . ? N2 Sm1 N1 C19 -65.57(9) 3 . . . ? N4 Sm1 N1 C19 180.000(1) . . . . ? N3 Sm1 N1 C19 0.000(1) . . . . ? C2 Sm1 N1 C19 -124.1(3) 3 . . . ? C2 Sm1 N1 C19 124.1(3) . . . . ? C9 Sm1 N1 C19 29.25(13) . . . . ? C9 Sm1 N1 C19 -29.25(13) 3 . . . ? C1 Sm1 N1 C19 -160.54(16) 3 . . . ? C1 Sm1 N1 C19 160.54(16) . . . . ? C10 Sm1 N1 C19 31.3(2) . . . . ? N2 Sm1 N2 C4 78.5(4) 3 . . . ? N4 Sm1 N2 C4 -105.3(4) . . . . ? N3 Sm1 N2 C4 138.6(4) . . . . ? N1 Sm1 N2 C4 18.6(3) . . . . ? C2 Sm1 N2 C4 13.8(4) 3 . . . ? C2 Sm1 N2 C4 -9.0(3) . . . . ? C9 Sm1 N2 C4 166.1(4) . . . . ? C9 Sm1 N2 C4 143.5(3) 3 . . . ? C1 Sm1 N2 C4 -13.8(4) 3 . . . ? C1 Sm1 N2 C4 -26.9(3) . . . . ? C10 Sm1 N2 C4 -176.3(3) . . . . ? N2 Sm1 N2 C7 -77.9(4) 3 . . . ? N4 Sm1 N2 C7 98.2(4) . . . . ? N3 Sm1 N2 C7 -17.8(3) . . . . ? N1 Sm1 N2 C7 -137.9(4) . . . . ? C2 Sm1 N2 C7 -142.6(3) 3 . . . ? C2 Sm1 N2 C7 -165.4(4) . . . . ? C9 Sm1 N2 C7 9.7(3) . . . . ? C9 Sm1 N2 C7 -12.9(4) 3 . . . ? C1 Sm1 N2 C7 -170.2(3) 3 . . . ? C1 Sm1 N2 C7 176.6(4) . . . . ? C10 Sm1 N2 C7 27.3(3) . . . . ? N2 Sm1 N3 C9 59.0(3) . . . . ? N2 Sm1 N3 C9 -169.9(3) 3 . . . ? N4 Sm1 N3 C9 -55.5(3) . . . . ? N1 Sm1 N3 C9 124.5(3) . . . . ? C2 Sm1 N3 C9 154.0(3) 3 . . . ? C2 Sm1 N3 C9 95.0(3) . . . . ? C9 Sm1 N3 C9 -110.9(5) 3 . . . ? C1 Sm1 N3 C9 156.5(3) 3 . . . ? C1 Sm1 N3 C9 92.6(4) . . . . ? C10 Sm1 N3 C9 -36.1(3) . . . . ? N2 Sm1 N3 C9 169.9(3) . . . 3 ? N2 Sm1 N3 C9 -59.0(3) 3 . . 3 ? N4 Sm1 N3 C9 55.5(3) . . . 3 ? N1 Sm1 N3 C9 -124.5(3) . . . 3 ? C2 Sm1 N3 C9 -95.0(3) 3 . . 3 ? C2 Sm1 N3 C9 -154.0(3) . . . 3 ? C9 Sm1 N3 C9 110.9(5) . . . 3 ? C1 Sm1 N3 C9 -92.6(4) 3 . . 3 ? C1 Sm1 N3 C9 -156.5(3) . . . 3 ? C10 Sm1 N3 C9 74.9(3) . . . 3 ? N2 Sm1 N3 C20 -65.53(9) . . . . ? N2 Sm1 N3 C20 65.53(9) 3 . . . ? N4 Sm1 N3 C20 180.000(1) . . . . ? N1 Sm1 N3 C20 0.000(2) . . . . ? C2 Sm1 N3 C20 29.51(13) 3 . . . ? C2 Sm1 N3 C20 -29.51(13) . . . . ? C9 Sm1 N3 C20 -124.5(3) . . . . ? C9 Sm1 N3 C20 124.5(3) 3 . . . ? C1 Sm1 N3 C20 32.0(3) 3 . . . ? C1 Sm1 N3 C20 -32.0(3) . . . . ? C10 Sm1 N3 C20 -160.59(14) . . . . ? N2 Sm1 N4 C21 91.84(18) . . . . ? N2 Sm1 N4 C21 -91.84(17) 3 . . . ? N3 Sm1 N4 C21 180.00(5) . . . . ? N1 Sm1 N4 C21 0.00(5) . . . . ? C2 Sm1 N4 C21 -24.59(12) 3 . . . ? C2 Sm1 N4 C21 24.59(12) . . . . ? C9 Sm1 N4 C21 156.41(12) . . . . ? C9 Sm1 N4 C21 -156.41(11) 3 . . . ? C1 Sm1 N4 C21 -13.78(12) 3 . . . ? C1 Sm1 N4 C21 13.78(12) . . . . ? C10 Sm1 N4 C21 166.09(11) . . . . ? N7 Sm2 N5 C26 73.1(4) . . . . ? N8 Sm2 N5 C26 -106.9(4) . . . . ? N6 Sm2 N5 C26 133.8(5) 3 . . . ? N6 Sm2 N5 C26 12.4(4) . . . . ? C31 Sm2 N5 C26 138.1(4) 3 . . . ? C31 Sm2 N5 C26 8.0(5) . . . . ? C28 Sm2 N5 C26 -14.3(4) . . . . ? C28 Sm2 N5 C26 160.4(5) 3 . . . ? C30 Sm2 N5 C26 165.8(4) 3 . . . ? C30 Sm2 N5 C26 -19.7(5) . . . . ? C29 Sm2 N5 C26 -32.5(4) . . . . ? N7 Sm2 N5 C26 -73.1(4) . . . 3 ? N8 Sm2 N5 C26 106.9(4) . . . 3 ? N6 Sm2 N5 C26 -12.4(4) 3 . . 3 ? N6 Sm2 N5 C26 -133.8(5) . . . 3 ? C31 Sm2 N5 C26 -8.0(5) 3 . . 3 ? C31 Sm2 N5 C26 -138.1(4) . . . 3 ? C28 Sm2 N5 C26 -160.4(5) . . . 3 ? C28 Sm2 N5 C26 14.3(4) 3 . . 3 ? C30 Sm2 N5 C26 19.7(5) 3 . . 3 ? C30 Sm2 N5 C26 -165.8(4) . . . 3 ? C29 Sm2 N5 C26 -178.7(5) . . . 3 ? N7 Sm2 N6 C31 57.1(3) . . . . ? N5 Sm2 N6 C31 -170.9(3) . . . . ? N8 Sm2 N6 C31 -50.1(4) . . . . ? N6 Sm2 N6 C31 123.4(2) 3 . . . ? C31 Sm2 N6 C31 94.2(3) 3 . . . ? C28 Sm2 N6 C31 -113.2(3) . . . . ? C28 Sm2 N6 C31 153.0(3) 3 . . . ? C30 Sm2 N6 C31 91.2(4) 3 . . . ? C30 Sm2 N6 C31 -37.4(3) . . . . ? C29 Sm2 N6 C31 -76.9(3) . . . . ? N7 Sm2 N6 C28 170.3(3) . . . . ? N5 Sm2 N6 C28 -57.7(3) . . . . ? N8 Sm2 N6 C28 63.1(4) . . . . ? N6 Sm2 N6 C28 -123.4(2) 3 . . . ? C31 Sm2 N6 C28 -152.6(3) 3 . . . ? C31 Sm2 N6 C28 113.2(3) . . . . ? C28 Sm2 N6 C28 -93.8(3) 3 . . . ? C30 Sm2 N6 C28 -155.6(3) 3 . . . ? C30 Sm2 N6 C28 75.8(3) . . . . ? C29 Sm2 N6 C28 36.3(3) . . . . ? N7 Sm2 N6 C43 -66.6(3) . . . . ? N5 Sm2 N6 C43 65.4(3) . . . . ? N8 Sm2 N6 C43 -173.8(4) . . . . ? N6 Sm2 N6 C43 -0.3(5) 3 . . . ? C31 Sm2 N6 C43 -29.5(4) 3 . . . ? C31 Sm2 N6 C43 -123.7(5) . . . . ? C28 Sm2 N6 C43 123.1(5) . . . . ? C28 Sm2 N6 C43 29.3(4) 3 . . . ? C30 Sm2 N6 C43 -32.5(5) 3 . . . ? C30 Sm2 N6 C43 -161.1(4) . . . . ? C29 Sm2 N6 C43 159.4(4) . . . . ? N5 Sm2 N7 C33 -72.9(4) . . . . ? N8 Sm2 N7 C33 107.1(4) . . . . ? N6 Sm2 N7 C33 -133.4(4) 3 . . . ? N6 Sm2 N7 C33 -12.3(4) . . . . ? C31 Sm2 N7 C33 -159.6(5) 3 . . . ? C31 Sm2 N7 C33 13.8(4) . . . . ? C28 Sm2 N7 C33 -7.7(4) . . . . ? C28 Sm2 N7 C33 -138.1(4) 3 . . . ? C30 Sm2 N7 C33 -178.2(4) 3 . . . ? C30 Sm2 N7 C33 32.4(4) . . . . ? C29 Sm2 N7 C33 19.6(4) . . . . ? N5 Sm2 N7 C33 72.9(4) . . . 3 ? N8 Sm2 N7 C33 -107.1(4) . . . 3 ? N6 Sm2 N7 C33 12.3(4) 3 . . 3 ? N6 Sm2 N7 C33 133.4(4) . . . 3 ? C31 Sm2 N7 C33 -13.8(4) 3 . . 3 ? C31 Sm2 N7 C33 159.6(5) . . . 3 ? C28 Sm2 N7 C33 138.1(4) . . . 3 ? C28 Sm2 N7 C33 7.7(4) 3 . . 3 ? C30 Sm2 N7 C33 -32.4(4) 3 . . 3 ? C30 Sm2 N7 C33 178.2(4) . . . 3 ? C29 Sm2 N7 C33 165.3(4) . . . 3 ? N7 Sm2 N8 C44 180.00(19) . . . . ? N5 Sm2 N8 C44 0.00(19) . . . . ? N6 Sm2 N8 C44 93.5(3) 3 . . . ? N6 Sm2 N8 C44 -93.5(3) . . . . ? C31 Sm2 N8 C44 114.9(2) 3 . . . ? C31 Sm2 N8 C44 -114.9(2) . . . . ? C28 Sm2 N8 C44 -67.5(2) . . . . ? C28 Sm2 N8 C44 67.5(2) 3 . . . ? C30 Sm2 N8 C44 102.5(2) 3 . . . ? C30 Sm2 N8 C44 -102.5(2) . . . . ? C29 Sm2 N8 C44 -74.9(2) . . . . ? N2 Sm1 C1 C2 36.9(3) . . . . ? N2 Sm1 C1 C2 -85.4(3) 3 . . . ? N4 Sm1 C1 C2 156.8(3) . . . . ? N3 Sm1 C1 C2 4.4(5) . . . . ? N1 Sm1 C1 C2 -38.8(3) . . . . ? C2 Sm1 C1 C2 -79.4(4) 3 . . . ? C9 Sm1 C1 C2 56.2(4) . . . . ? C9 Sm1 C1 C2 -84.8(8) 3 . . . ? C1 Sm1 C1 C2 -114.8(3) 3 . . . ? C10 Sm1 C1 C2 102.3(3) . . . . ? N2 Sm1 C1 C1 151.71(8) . . . 3 ? N2 Sm1 C1 C1 29.43(8) 3 . . 3 ? N4 Sm1 C1 C1 -88.37(6) . . . 3 ? N3 Sm1 C1 C1 119.2(3) . . . 3 ? N1 Sm1 C1 C1 76.03(13) . . . 3 ? C2 Sm1 C1 C1 35.40(18) 3 . . 3 ? C2 Sm1 C1 C1 114.8(3) . . . 3 ? C9 Sm1 C1 C1 171.0(2) . . . 3 ? C9 Sm1 C1 C1 30.0(7) 3 . . 3 ? C10 Sm1 C1 C1 -142.9(2) . . . 3 ? C1 C1 C2 N1 -1.5(4) 3 . . . ? Sm1 C1 C2 N1 67.3(4) . . . . ? C1 C1 C2 C3 177.8(4) 3 . . . ? Sm1 C1 C2 C3 -113.4(5) . . . . ? C1 C1 C2 Sm1 -68.79(13) 3 . . . ? C2 N1 C2 C1 2.4(7) 3 . . . ? C19 N1 C2 C1 -177.8(6) . . . . ? Sm1 N1 C2 C1 -72.7(4) . . . . ? C2 N1 C2 C3 -177.0(3) 3 . . . ? C19 N1 C2 C3 2.8(9) . . . . ? Sm1 N1 C2 C3 107.9(5) . . . . ? C2 N1 C2 Sm1 75.1(4) 3 . . . ? C19 N1 C2 Sm1 -105.1(6) . . . . ? N2 Sm1 C2 C1 -137.5(3) . . . . ? N2 Sm1 C2 C1 101.9(3) 3 . . . ? N4 Sm1 C2 C1 -24.3(3) . . . . ? N3 Sm1 C2 C1 -177.6(3) . . . . ? N1 Sm1 C2 C1 111.4(4) . . . . ? C2 Sm1 C2 C1 73.8(3) 3 . . . ? C9 Sm1 C2 C1 -142.8(3) . . . . ? C9 Sm1 C2 C1 157.7(3) 3 . . . ? C1 Sm1 C2 C1 36.0(3) 3 . . . ? C10 Sm1 C2 C1 -116.5(3) . . . . ? N2 Sm1 C2 N1 111.0(3) . . . . ? N2 Sm1 C2 N1 -9.6(3) 3 . . . ? N4 Sm1 C2 N1 -135.7(3) . . . . ? N3 Sm1 C2 N1 71.0(3) . . . . ? C2 Sm1 C2 N1 -37.6(3) 3 . . . ? C9 Sm1 C2 N1 105.8(3) . . . . ? C9 Sm1 C2 N1 46.2(5) 3 . . . ? C1 Sm1 C2 N1 -75.4(3) 3 . . . ? C1 Sm1 C2 N1 -111.4(4) . . . . ? C10 Sm1 C2 N1 132.0(3) . . . . ? N2 Sm1 C2 C3 -8.4(3) . . . . ? N2 Sm1 C2 C3 -129.1(3) 3 . . . ? N4 Sm1 C2 C3 104.8(3) . . . . ? N3 Sm1 C2 C3 -48.5(4) . . . . ? N1 Sm1 C2 C3 -119.5(5) . . . . ? C2 Sm1 C2 C3 -157.1(3) 3 . . . ? C9 Sm1 C2 C3 -13.7(4) . . . . ? C9 Sm1 C2 C3 -73.2(5) 3 . . . ? C1 Sm1 C2 C3 165.1(4) 3 . . . ? C1 Sm1 C2 C3 129.1(5) . . . . ? C10 Sm1 C2 C3 12.6(4) . . . . ? C1 C2 C3 C4 118.9(6) . . . . ? N1 C2 C3 C4 -61.9(6) . . . . ? Sm1 C2 C3 C4 21.9(5) . . . . ? C1 C2 C3 C11 -117.9(6) . . . . ? N1 C2 C3 C11 61.3(6) . . . . ? Sm1 C2 C3 C11 145.2(3) . . . . ? C1 C2 C3 C13 1.7(8) . . . . ? N1 C2 C3 C13 -179.1(5) . . . . ? Sm1 C2 C3 C13 -95.2(4) . . . . ? C7 N2 C4 C5 -0.3(5) . . . . ? Sm1 N2 C4 C5 -160.4(3) . . . . ? C7 N2 C4 C3 -173.5(4) . . . . ? Sm1 N2 C4 C3 26.4(6) . . . . ? C2 C3 C4 N2 -31.3(6) . . . . ? C11 C3 C4 N2 -154.6(4) . . . . ? C13 C3 C4 N2 85.9(6) . . . . ? C2 C3 C4 C5 156.8(5) . . . . ? C11 C3 C4 C5 33.6(7) . . . . ? C13 C3 C4 C5 -85.9(6) . . . . ? N2 C4 C5 C6 0.1(6) . . . . ? C3 C4 C5 C6 172.6(5) . . . . ? C4 C5 C6 C7 0.1(6) . . . . ? C4 N2 C7 C6 0.3(5) . . . . ? Sm1 N2 C7 C6 160.6(3) . . . . ? C4 N2 C7 C8 171.8(5) . . . . ? Sm1 N2 C7 C8 -27.9(6) . . . . ? C5 C6 C7 N2 -0.3(6) . . . . ? C5 C6 C7 C8 -170.9(5) . . . . ? N2 C7 C8 C9 32.6(6) . . . . ? C6 C7 C8 C9 -157.5(5) . . . . ? N2 C7 C8 C15 -88.5(5) . . . . ? C6 C7 C8 C15 81.3(7) . . . . ? N2 C7 C8 C17 154.3(4) . . . . ? C6 C7 C8 C17 -35.9(7) . . . . ? C9 N3 C9 C10 -3.2(7) 3 . . . ? C20 N3 C9 C10 -178.8(6) . . . . ? Sm1 N3 C9 C10 74.3(4) . . . . ? C9 N3 C9 C8 176.7(3) 3 . . . ? C20 N3 C9 C8 1.2(9) . . . . ? Sm1 N3 C9 C8 -105.7(5) . . . . ? C9 N3 C9 Sm1 -77.5(4) 3 . . . ? C20 N3 C9 Sm1 106.9(6) . . . . ? C7 C8 C9 C10 -121.1(6) . . . . ? C15 C8 C9 C10 0.3(8) . . . . ? C17 C8 C9 C10 116.6(6) . . . . ? C7 C8 C9 N3 59.0(7) . . . . ? C15 C8 C9 N3 -179.7(5) . . . . ? C17 C8 C9 N3 -63.4(6) . . . . ? C7 C8 C9 Sm1 -22.1(5) . . . . ? C15 C8 C9 Sm1 99.2(4) . . . . ? C17 C8 C9 Sm1 -144.5(3) . . . . ? N2 Sm1 C9 C10 137.7(3) . . . . ? N2 Sm1 C9 C10 -101.6(3) 3 . . . ? N4 Sm1 C9 C10 21.6(3) . . . . ? N3 Sm1 C9 C10 -111.6(4) . . . . ? N1 Sm1 C9 C10 178.0(3) . . . . ? C2 Sm1 C9 C10 -156.5(3) 3 . . . ? C2 Sm1 C9 C10 143.0(3) . . . . ? C9 Sm1 C9 C10 -73.5(3) 3 . . . ? C1 Sm1 C9 C10 138.4(7) 3 . . . ? C1 Sm1 C9 C10 116.0(3) . . . . ? N2 Sm1 C9 N3 -110.7(3) . . . . ? N2 Sm1 C9 N3 10.0(3) 3 . . . ? N4 Sm1 C9 N3 133.1(3) . . . . ? N1 Sm1 C9 N3 -70.5(3) . . . . ? C2 Sm1 C9 N3 -45.0(5) 3 . . . ? C2 Sm1 C9 N3 -105.5(3) . . . . ? C9 Sm1 C9 N3 38.0(3) 3 . . . ? C1 Sm1 C9 N3 -110.0(8) 3 . . . ? C1 Sm1 C9 N3 -132.4(3) . . . . ? C10 Sm1 C9 N3 111.6(4) . . . . ? N2 Sm1 C9 C8 7.9(3) . . . . ? N2 Sm1 C9 C8 128.6(3) 3 . . . ? N4 Sm1 C9 C8 -108.2(3) . . . . ? N3 Sm1 C9 C8 118.6(4) . . . . ? N1 Sm1 C9 C8 48.2(4) . . . . ? C2 Sm1 C9 C8 73.7(5) 3 . . . ? C2 Sm1 C9 C8 13.2(4) . . . . ? C9 Sm1 C9 C8 156.7(3) 3 . . . ? C1 Sm1 C9 C8 8.6(9) 3 . . . ? C1 Sm1 C9 C8 -13.8(4) . . . . ? C10 Sm1 C9 C8 -129.8(5) . . . . ? N3 C9 C10 C10 2.0(4) . . . 3 ? C8 C9 C10 C10 -178.0(4) . . . 3 ? Sm1 C9 C10 C10 68.37(13) . . . 3 ? N3 C9 C10 Sm1 -66.4(4) . . . . ? C8 C9 C10 Sm1 113.6(5) . . . . ? N2 Sm1 C10 C9 -36.8(3) . . . . ? N2 Sm1 C10 C9 85.4(3) 3 . . . ? N4 Sm1 C10 C9 -158.3(3) . . . . ? N3 Sm1 C10 C9 38.9(3) . . . . ? N1 Sm1 C10 C9 -3.6(5) . . . . ? C2 Sm1 C10 C9 83.8(7) 3 . . . ? C2 Sm1 C10 C9 -55.4(4) . . . . ? C9 Sm1 C10 C9 79.7(4) 3 . . . ? C1 Sm1 C10 C9 -158.0(4) 3 . . . ? C1 Sm1 C10 C9 -102.2(4) . . . . ? N2 Sm1 C10 C10 -151.69(8) . . . 3 ? N2 Sm1 C10 C10 -29.41(8) 3 . . 3 ? N4 Sm1 C10 C10 86.82(6) . . . 3 ? N3 Sm1 C10 C10 -75.97(12) . . . 3 ? N1 Sm1 C10 C10 -118.4(2) . . . 3 ? C2 Sm1 C10 C10 -31.0(7) 3 . . 3 ? C2 Sm1 C10 C10 -170.3(2) . . . 3 ? C9 Sm1 C10 C10 -114.8(3) . . . 3 ? C9 Sm1 C10 C10 -35.17(18) 3 . . 3 ? C1 Sm1 C10 C10 87.2(5) 3 . . 3 ? C1 Sm1 C10 C10 142.9(2) . . . 3 ? C2 C3 C11 C12 53.8(6) . . . . ? C4 C3 C11 C12 177.0(5) . . . . ? C13 C3 C11 C12 -64.8(6) . . . . ? C2 C3 C13 C14 176.3(8) . . . . ? C4 C3 C13 C14 57.1(9) . . . . ? C11 C3 C13 C14 -63.2(9) . . . . ? C7 C8 C15 C16 46.1(6) . . . . ? C9 C8 C15 C16 -76.2(6) . . . . ? C17 C8 C15 C16 165.8(5) . . . . ? C7 C8 C17 C18 -173.7(5) . . . . ? C9 C8 C17 C18 -50.9(6) . . . . ? C15 C8 C17 C18 67.2(6) . . . . ? Sm1 N4 C21 C22 180.00(3) . . . . ? N4 C21 C22 C23 -122.2(6) . . . 3 ? N4 C21 C22 C23 122.2(6) . . . . ? N4 C21 C22 C24 0.00(4) . . . . ? C26 N5 C26 C25 -0.4(7) 3 . . . ? Sm2 N5 C26 C25 -151.7(3) . . . . ? C26 N5 C26 C27 -171.7(3) 3 . . . ? Sm2 N5 C26 C27 37.0(6) . . . . ? C25 C25 C26 N5 0.2(5) 3 . . . ? C25 C25 C26 C27 170.6(4) 3 . . . ? N5 C26 C27 C28 -40.6(6) . . . . ? C25 C26 C27 C28 149.7(5) . . . . ? N5 C26 C27 C37 -164.4(5) . . . . ? C25 C26 C27 C37 25.9(7) . . . . ? N5 C26 C27 C35 74.0(6) . . . . ? C25 C26 C27 C35 -95.7(6) . . . . ? C31 N6 C28 C29 1.4(5) . . . . ? C43 N6 C28 C29 -179.9(4) . . . . ? Sm2 N6 C28 C29 -73.1(3) . . . . ? C31 N6 C28 C27 -179.7(5) . . . . ? C43 N6 C28 C27 -1.0(6) . . . . ? Sm2 N6 C28 C27 105.8(4) . . . . ? C31 N6 C28 Sm2 74.5(3) . . . . ? C43 N6 C28 Sm2 -106.8(4) . . . . ? C26 C27 C28 C29 120.6(5) . . . . ? C37 C27 C28 C29 -115.5(6) . . . . ? C35 C27 C28 C29 4.8(7) . . . . ? C26 C27 C28 N6 -58.1(6) . . . . ? C37 C27 C28 N6 65.8(6) . . . . ? C35 C27 C28 N6 -173.8(4) . . . . ? C26 C27 C28 Sm2 25.3(5) . . . . ? C37 C27 C28 Sm2 149.2(3) . . . . ? C35 C27 C28 Sm2 -90.5(4) . . . . ? N7 Sm2 C28 C29 101.8(3) . . . . ? N5 Sm2 C28 C29 -136.0(3) . . . . ? N8 Sm2 C28 C29 -16.4(4) . . . . ? N6 Sm2 C28 C29 -176.2(3) 3 . . . ? N6 Sm2 C28 C29 111.5(4) . . . . ? C31 Sm2 C28 C29 158.8(3) 3 . . . ? C31 Sm2 C28 C29 75.0(3) . . . . ? C28 Sm2 C28 C29 -141.7(2) 3 . . . ? C30 Sm2 C28 C29 -135.4(6) 3 . . . ? C30 Sm2 C28 C29 36.6(3) . . . . ? N7 Sm2 C28 N6 -9.7(3) . . . . ? N5 Sm2 C28 N6 112.5(3) . . . . ? N8 Sm2 C28 N6 -128.0(3) . . . . ? N6 Sm2 C28 N6 72.3(3) 3 . . . ? C31 Sm2 C28 N6 47.2(5) 3 . . . ? C31 Sm2 C28 N6 -36.5(2) . . . . ? C28 Sm2 C28 N6 106.8(3) 3 . . . ? C30 Sm2 C28 N6 113.0(7) 3 . . . ? C30 Sm2 C28 N6 -74.9(3) . . . . ? C29 Sm2 C28 N6 -111.5(4) . . . . ? N7 Sm2 C28 C27 -129.9(3) . . . . ? N5 Sm2 C28 C27 -7.8(3) . . . . ? N8 Sm2 C28 C27 111.8(4) . . . . ? N6 Sm2 C28 C27 -47.9(4) 3 . . . ? N6 Sm2 C28 C27 -120.2(5) . . . . ? C31 Sm2 C28 C27 -73.0(5) 3 . . . ? C31 Sm2 C28 C27 -156.7(4) . . . . ? C28 Sm2 C28 C27 -13.4(5) 3 . . . ? C30 Sm2 C28 C27 -7.2(9) 3 . . . ? C30 Sm2 C28 C27 164.9(4) . . . . ? C29 Sm2 C28 C27 128.3(5) . . . . ? N6 C28 C29 C30 -0.9(6) . . . . ? C27 C28 C29 C30 -179.8(5) . . . . ? Sm2 C28 C29 C30 -68.7(4) . . . . ? N6 C28 C29 Sm2 67.8(3) . . . . ? C27 C28 C29 Sm2 -111.0(5) . . . . ? N7 Sm2 C29 C28 -85.5(3) . . . . ? N5 Sm2 C29 C28 38.3(3) . . . . ? N8 Sm2 C29 C28 164.1(4) . . . . ? N6 Sm2 C29 C28 6.9(5) 3 . . . ? N6 Sm2 C29 C28 -38.5(3) . . . . ? C31 Sm2 C29 C28 -81.2(8) 3 . . . ? C31 Sm2 C29 C28 -78.2(3) . . . . ? C28 Sm2 C29 C28 57.2(3) 3 . . . ? C30 Sm2 C29 C28 156.6(4) 3 . . . ? C30 Sm2 C29 C28 -114.2(4) . . . . ? N7 Sm2 C29 C30 28.7(3) . . . . ? N5 Sm2 C29 C30 152.5(3) . . . . ? N8 Sm2 C29 C30 -81.7(3) . . . . ? N6 Sm2 C29 C30 121.1(3) 3 . . . ? N6 Sm2 C29 C30 75.6(3) . . . . ? C31 Sm2 C29 C30 33.0(9) 3 . . . ? C31 Sm2 C29 C30 35.9(3) . . . . ? C28 Sm2 C29 C30 114.2(4) . . . . ? C28 Sm2 C29 C30 171.4(3) 3 . . . ? C30 Sm2 C29 C30 -89.3(5) 3 . . . ? C28 C29 C30 C31 0.2(6) . . . . ? Sm2 C29 C30 C31 -67.1(3) . . . . ? C28 C29 C30 Sm2 67.2(4) . . . . ? N7 Sm2 C30 C31 -38.4(3) . . . . ? N5 Sm2 C30 C31 85.5(3) . . . . ? N8 Sm2 C30 C31 -152.5(4) . . . . ? N6 Sm2 C30 C31 -5.2(5) 3 . . . ? N6 Sm2 C30 C31 38.3(3) . . . . ? C31 Sm2 C30 C31 -56.4(3) 3 . . . ? C28 Sm2 C30 C31 78.7(3) . . . . ? C28 Sm2 C30 C31 86.0(7) 3 . . . ? C30 Sm2 C30 C31 -104.1(4) 3 . . . ? C29 Sm2 C30 C31 114.0(5) . . . . ? N7 Sm2 C30 C29 -152.5(3) . . . . ? N5 Sm2 C30 C29 -28.6(3) . . . . ? N8 Sm2 C30 C29 93.4(4) . . . . ? N6 Sm2 C30 C29 -119.2(4) 3 . . . ? N6 Sm2 C30 C29 -75.7(3) . . . . ? C31 Sm2 C30 C29 -170.4(3) 3 . . . ? C31 Sm2 C30 C29 -114.0(5) . . . . ? C28 Sm2 C30 C29 -35.4(3) . . . . ? C28 Sm2 C30 C29 -28.0(8) 3 . . . ? C30 Sm2 C30 C29 141.8(3) 3 . . . ? C28 N6 C31 C30 -1.3(4) . . . . ? C43 N6 C31 C30 180.0(4) . . . . ? Sm2 N6 C31 C30 73.4(3) . . . . ? C28 N6 C31 C32 178.8(5) . . . . ? C43 N6 C31 C32 0.0(7) . . . . ? Sm2 N6 C31 C32 -106.5(5) . . . . ? C28 N6 C31 Sm2 -74.7(3) . . . . ? C43 N6 C31 Sm2 106.5(4) . . . . ? C29 C30 C31 N6 0.7(5) . . . . ? Sm2 C30 C31 N6 -68.7(3) . . . . ? C29 C30 C31 C32 -179.4(5) . . . . ? Sm2 C30 C31 C32 111.3(5) . . . . ? C29 C30 C31 Sm2 69.4(4) . . . . ? N7 Sm2 C31 N6 -113.4(3) . . . . ? N5 Sm2 C31 N6 9.0(3) . . . . ? N8 Sm2 C31 N6 138.3(3) . . . . ? N6 Sm2 C31 N6 -72.1(3) 3 . . . ? C31 Sm2 C31 N6 -106.2(3) 3 . . . ? C28 Sm2 C31 N6 36.9(2) . . . . ? C28 Sm2 C31 N6 -46.4(5) 3 . . . ? C30 Sm2 C31 N6 -133.6(3) 3 . . . ? C30 Sm2 C31 N6 110.7(4) . . . . ? C29 Sm2 C31 N6 74.4(3) . . . . ? N7 Sm2 C31 C30 135.9(4) . . . . ? N5 Sm2 C31 C30 -101.7(3) . . . . ? N8 Sm2 C31 C30 27.6(4) . . . . ? N6 Sm2 C31 C30 177.2(3) 3 . . . ? N6 Sm2 C31 C30 -110.7(4) . . . . ? C31 Sm2 C31 C30 143.0(3) 3 . . . ? C28 Sm2 C31 C30 -73.8(3) . . . . ? C28 Sm2 C31 C30 -157.1(3) 3 . . . ? C30 Sm2 C31 C30 115.7(4) 3 . . . ? C29 Sm2 C31 C30 -36.3(3) . . . . ? N7 Sm2 C31 C32 7.8(3) . . . . ? N5 Sm2 C31 C32 130.2(3) . . . . ? N8 Sm2 C31 C32 -100.5(4) . . . . ? N6 Sm2 C31 C32 49.1(4) 3 . . . ? N6 Sm2 C31 C32 121.2(4) . . . . ? C31 Sm2 C31 C32 14.9(5) 3 . . . ? C28 Sm2 C31 C32 158.1(4) . . . . ? C28 Sm2 C31 C32 74.8(5) 3 . . . ? C30 Sm2 C31 C32 -12.4(4) 3 . . . ? C30 Sm2 C31 C32 -128.1(5) . . . . ? C29 Sm2 C31 C32 -164.4(4) . . . . ? N6 C31 C32 C33 59.4(6) . . . . ? C30 C31 C32 C33 -120.5(5) . . . . ? Sm2 C31 C32 C33 -25.2(4) . . . . ? N6 C31 C32 C41 177.6(4) . . . . ? C30 C31 C32 C41 -2.4(7) . . . . ? Sm2 C31 C32 C41 92.9(4) . . . . ? N6 C31 C32 C39 -62.4(6) . . . . ? C30 C31 C32 C39 117.7(5) . . . . ? Sm2 C31 C32 C39 -147.1(3) . . . . ? C33 N7 C33 C34 -2.1(7) 3 . . . ? Sm2 N7 C33 C34 149.0(4) . . . . ? C33 N7 C33 C32 173.1(3) 3 . . . ? Sm2 N7 C33 C32 -35.8(6) . . . . ? C31 C32 C33 C34 -146.3(5) . . . . ? C41 C32 C33 C34 95.6(6) . . . . ? C39 C32 C33 C34 -24.3(7) . . . . ? C31 C32 C33 N7 39.6(6) . . . . ? C41 C32 C33 N7 -78.4(6) . . . . ? C39 C32 C33 N7 161.7(5) . . . . ? N7 C33 C34 C34 1.3(4) . . . 3 ? C32 C33 C34 C34 -173.1(4) . . . 3 ? C26 C27 C35 C36 60.6(6) . . . . ? C28 C27 C35 C36 177.9(4) . . . . ? C37 C27 C35 C36 -61.5(6) . . . . ? C26 C27 C37 C38 -178.5(4) . . . . ? C28 C27 C37 C38 58.6(6) . . . . ? C35 C27 C37 C38 -58.7(6) . . . . ? C31 C32 C39 C40 -46.7(6) . . . . ? C33 C32 C39 C40 -168.7(4) . . . . ? C41 C32 C39 C40 72.3(6) . . . . ? C31 C32 C41 C42 -174.5(4) . . . . ? C33 C32 C41 C42 -55.0(6) . . . . ? C39 C32 C41 C42 65.0(6) . . . . ? Sm2 N8 C44 C45 180.00(18) . . . . ? N8 C44 C45 C47 180.000(15) . . . . ? N8 C44 C45 C46 -58.8(7) . . . . ? N8 C44 C45 C46 58.8(7) . . . 3 ? C49 C48 C49 C50 1.4(12) 3_655 . . . ? C48 C49 C50 C51 -2.3(11) . . . . ? C49 C50 C51 C50 3.1(13) . . . 3_655 ? C53 C52 C53 C54 0.4(16) 3 . . . ? C52 C53 C54 C55 -0.8(13) . . . . ? C53 C54 C55 C54 1.1(17) . . . 3 ? _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.67 _diffrn_measured_fraction_theta_full 0.944 _refine_diff_density_max 1.138 _refine_diff_density_min -1.598 _refine_diff_density_rms 0.082 # Attachment 'compound_5.cif' data_cj626 _database_code_depnum_ccdc_archive 'CCDC 765859' #TrackingRef 'compound_5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C89 H132 N8 P2 Sm2' _chemical_formula_weight 1676.67 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.941(3) _cell_length_b 17.469(4) _cell_length_c 18.533(4) _cell_angle_alpha 112.38(3) _cell_angle_beta 91.11(3) _cell_angle_gamma 98.02(3) _cell_volume 4415(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1752 _exptl_absorpt_coefficient_mu 1.399 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.888 _exptl_absorpt_correction_T_max 0.924 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _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 28983 _diffrn_reflns_av_R_equivalents 0.1679 _diffrn_reflns_av_sigmaI/netI 0.2745 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.07 _reflns_number_total 15481 _reflns_number_gt 6948 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. one half of a molecule of hexane is located in the asymmetric unit. This was found to be disordered over 2 sites in a 70:30 ratio. The carbon atoms of both disordered sets were refined isotropically. The poor quality of the refinement and the high Rint value arise from the very weak data above the diffraction angle, theta = 20 deg. Despite this, the molecular connectivity within the structure is unambiguous. ; _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^)+(0.0666P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 15481 _refine_ls_number_parameters 952 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.2149 _refine_ls_R_factor_gt 0.0819 _refine_ls_wR_factor_ref 0.1881 _refine_ls_wR_factor_gt 0.1471 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Sm1 Sm 0.82540(4) 0.36044(4) 0.12945(4) 0.0329(2) Uani 1 1 d . . . Sm2 Sm 0.68595(4) 0.78192(4) 0.44707(4) 0.0301(2) Uani 1 1 d . . . P1 P 0.8017(2) 0.5321(2) 0.22817(19) 0.0380(8) Uani 1 1 d . . . P2 P 0.7493(2) 0.6479(2) 0.30941(18) 0.0349(8) Uani 1 1 d . . . N1 N 0.9387(6) 0.3600(6) 0.2310(5) 0.034(2) Uani 1 1 d . . . N2 N 0.7734(6) 0.2365(6) 0.0042(6) 0.039(3) Uani 1 1 d . . . N3 N 0.9844(6) 0.3338(6) 0.0546(5) 0.033(2) Uani 1 1 d . . . N4 N 0.7472(6) 0.2321(6) 0.1739(6) 0.034(2) Uani 1 1 d . . . N5 N 0.7202(6) 0.8925(6) 0.5830(5) 0.029(2) Uani 1 1 d . . . N6 N 0.5367(6) 0.7467(6) 0.3717(5) 0.032(2) Uani 1 1 d . . . N7 N 0.6660(6) 0.9311(5) 0.4302(5) 0.029(2) Uani 1 1 d . . . N8 N 0.5633(6) 0.7311(6) 0.5379(6) 0.032(2) Uani 1 1 d . . . C1 C 0.7470(8) 0.4828(8) 0.1401(7) 0.039(3) Uani 1 1 d . . . C2 C 0.6753(8) 0.5078(7) 0.0961(6) 0.034(3) Uani 1 1 d . . . C3 C 0.6553(8) 0.4436(8) 0.0120(7) 0.052(4) Uani 1 1 d . . . H3A H 0.6054 0.4574 -0.0135 0.078 Uiso 1 1 calc R . . H3B H 0.6382 0.3875 0.0122 0.078 Uiso 1 1 calc R . . H3C H 0.7095 0.4448 -0.0168 0.078 Uiso 1 1 calc R . . C4 C 0.5855(8) 0.5112(9) 0.1378(8) 0.051(4) Uani 1 1 d . . . H4A H 0.5963 0.5541 0.1911 0.077 Uiso 1 1 calc R . . H4B H 0.5642 0.4565 0.1399 0.077 Uiso 1 1 calc R . . H4C H 0.5394 0.5252 0.1085 0.077 Uiso 1 1 calc R . . C5 C 0.7080(8) 0.5932(8) 0.0951(7) 0.042(3) Uani 1 1 d . . . H5A H 0.7656 0.5924 0.0706 0.063 Uiso 1 1 calc R . . H5B H 0.7168 0.6352 0.1489 0.063 Uiso 1 1 calc R . . H5C H 0.6628 0.6073 0.0652 0.063 Uiso 1 1 calc R . . C6 C 0.8142(7) 0.7027(7) 0.3927(6) 0.028(3) Uani 1 1 d . . . C7 C 0.9098(7) 0.6998(7) 0.4202(7) 0.031(3) Uani 1 1 d . . . C8 C 0.9125(8) 0.6145(8) 0.4226(7) 0.044(4) Uani 1 1 d . . . H8A H 0.9027 0.5716 0.3692 0.066 Uiso 1 1 calc R . . H8B H 0.8648 0.6026 0.4541 0.066 Uiso 1 1 calc R . . H8C H 0.9718 0.6141 0.4459 0.066 Uiso 1 1 calc R . . C9 C 0.9754(7) 0.7134(8) 0.3641(7) 0.043(3) Uani 1 1 d . . . H9A H 0.9716 0.7674 0.3604 0.064 Uiso 1 1 calc R . . H9B H 0.9604 0.6682 0.3124 0.064 Uiso 1 1 calc R . . H9C H 1.0372 0.7136 0.3831 0.064 Uiso 1 1 calc R . . C10 C 0.9366(8) 0.7653(8) 0.5012(7) 0.049(4) Uani 1 1 d . . . H10A H 0.9937 0.7563 0.5212 0.074 Uiso 1 1 calc R . . H10B H 0.8891 0.7613 0.5359 0.074 Uiso 1 1 calc R . . H10C H 0.9445 0.8211 0.4993 0.074 Uiso 1 1 calc R . . C11 C 1.0327(8) 0.3710(7) 0.2272(6) 0.037(3) Uani 1 1 d . . . C12 C 1.0732(8) 0.3345(9) 0.2701(7) 0.050(4) Uani 1 1 d . . . H12 H 1.1362 0.3326 0.2748 0.060 Uiso 1 1 calc R . . C13 C 1.0065(9) 0.3008(9) 0.3054(7) 0.048(4) Uani 1 1 d . . . H13 H 1.0148 0.2720 0.3388 0.058 Uiso 1 1 calc R . . C14 C 0.9256(8) 0.3175(7) 0.2820(7) 0.035(3) Uani 1 1 d . . . C15 C 0.8255(8) 0.2102(8) -0.0602(7) 0.038(3) Uani 1 1 d . . . C16 C 0.7975(9) 0.1260(9) -0.1036(7) 0.050(4) Uani 1 1 d . . . H16 H 0.8228 0.0927 -0.1496 0.060 Uiso 1 1 calc R . . C17 C 0.7246(9) 0.0981(8) -0.0678(7) 0.050(4) Uani 1 1 d . . . H17 H 0.6918 0.0428 -0.0850 0.060 Uiso 1 1 calc R . . C18 C 0.7102(8) 0.1654(8) -0.0039(7) 0.036(3) Uani 1 1 d . . . C19 C 1.0104(8) 0.4123(8) 0.1152(6) 0.037(3) Uani 1 1 d . . . C20 C 0.9720(7) 0.4709(7) 0.0978(6) 0.027(3) Uani 1 1 d . . . H20 H 0.9786 0.5293 0.1287 0.032 Uiso 1 1 calc R . . C21 C 0.9211(7) 0.4277(7) 0.0253(7) 0.033(3) Uani 1 1 d . . . H21 H 0.8863 0.4526 -0.0006 0.040 Uiso 1 1 calc R . . C22 C 0.9292(7) 0.3443(7) -0.0024(6) 0.029(3) Uani 1 1 d . . . C23 C 1.0109(8) 0.2532(7) 0.0482(6) 0.039(3) Uani 1 1 d . . . H23A H 1.0668 0.2455 0.0212 0.059 Uiso 1 1 calc R . . H23B H 0.9624 0.2072 0.0185 0.059 Uiso 1 1 calc R . . H23C H 1.0213 0.2536 0.1007 0.059 Uiso 1 1 calc R . . C24 C 0.7586(8) 0.2987(9) 0.2452(7) 0.042(4) Uani 1 1 d . . . C25 C 0.6982(7) 0.3509(8) 0.2473(7) 0.033(3) Uani 1 1 d . . . H25 H 0.6917 0.4021 0.2888 0.040 Uiso 1 1 calc R . . C26 C 0.6477(8) 0.3125(9) 0.1746(7) 0.043(3) Uani 1 1 d . . . H26 H 0.6010 0.3353 0.1580 0.052 Uiso 1 1 calc R . . C27 C 0.6739(8) 0.2394(8) 0.1314(7) 0.035(3) Uani 1 1 d . . . C28 C 0.7983(9) 0.1634(8) 0.1481(7) 0.049(4) Uani 1 1 d . . . H28A H 0.8623 0.1846 0.1664 0.074 Uiso 1 1 calc R . . H28B H 0.7923 0.1371 0.0908 0.074 Uiso 1 1 calc R . . H28C H 0.7748 0.1219 0.1695 0.074 Uiso 1 1 calc R . . C29 C 1.0739(8) 0.4256(8) 0.1859(6) 0.036(3) Uani 1 1 d . . . C30 C 1.1700(7) 0.4057(8) 0.1610(7) 0.037(3) Uani 1 1 d . . . H30A H 1.2089 0.4154 0.2084 0.045 Uiso 1 1 calc R . . H30B H 1.1644 0.3455 0.1268 0.045 Uiso 1 1 calc R . . C31 C 1.2170(9) 0.4565(9) 0.1185(8) 0.063(4) Uani 1 1 d . . . H31A H 1.1757 0.4545 0.0759 0.095 Uiso 1 1 calc R . . H31B H 1.2711 0.4332 0.0968 0.095 Uiso 1 1 calc R . . H31C H 1.2348 0.5148 0.1552 0.095 Uiso 1 1 calc R . . C32 C 1.0806(8) 0.5181(7) 0.2428(6) 0.037(3) Uani 1 1 d . . . H32A H 1.1041 0.5544 0.2151 0.045 Uiso 1 1 calc R . . H32B H 1.0189 0.5294 0.2569 0.045 Uiso 1 1 calc R . . C33 C 1.1409(8) 0.5425(8) 0.3177(7) 0.051(4) Uani 1 1 d . . . H33A H 1.1217 0.5039 0.3435 0.076 Uiso 1 1 calc R . . H33B H 1.1359 0.5998 0.3528 0.076 Uiso 1 1 calc R . . H33C H 1.2040 0.5393 0.3050 0.076 Uiso 1 1 calc R . . C34 C 0.8901(8) 0.2732(7) -0.0801(7) 0.039(3) Uani 1 1 d . . . C35 C 0.9641(8) 0.2310(8) -0.1288(7) 0.043(3) Uani 1 1 d . . . H35A H 0.9944 0.2028 -0.1002 0.052 Uiso 1 1 calc R . . H35B H 0.9351 0.1871 -0.1786 0.052 Uiso 1 1 calc R . . C36 C 1.0358(9) 0.2902(8) -0.1475(7) 0.056(4) Uani 1 1 d . . . H36A H 1.0077 0.3136 -0.1809 0.084 Uiso 1 1 calc R . . H36B H 1.0831 0.2593 -0.1748 0.084 Uiso 1 1 calc R . . H36C H 1.0627 0.3357 -0.0987 0.084 Uiso 1 1 calc R . . C37 C 0.8361(8) 0.3136(8) -0.1238(6) 0.040(3) Uani 1 1 d . . . H37A H 0.7880 0.3385 -0.0909 0.048 Uiso 1 1 calc R . . H37B H 0.8774 0.3600 -0.1298 0.048 Uiso 1 1 calc R . . C38 C 0.7926(10) 0.2546(8) -0.2039(7) 0.062(4) Uani 1 1 d . . . H38A H 0.8400 0.2367 -0.2397 0.094 Uiso 1 1 calc R . . H38B H 0.7533 0.2836 -0.2242 0.094 Uiso 1 1 calc R . . H38C H 0.7564 0.2054 -0.1997 0.094 Uiso 1 1 calc R . . C39 C 0.6374(8) 0.1740(8) 0.0509(7) 0.041(3) Uani 1 1 d . . . C40 C 0.5571(7) 0.2074(8) 0.0212(7) 0.042(3) Uani 1 1 d . . . H40A H 0.5136 0.2222 0.0621 0.050 Uiso 1 1 calc R . . H40B H 0.5817 0.2592 0.0135 0.050 Uiso 1 1 calc R . . C41 C 0.5070(10) 0.1442(9) -0.0548(8) 0.070(5) Uani 1 1 d . . . H41A H 0.5510 0.1191 -0.0917 0.105 Uiso 1 1 calc R . . H41B H 0.4696 0.1726 -0.0774 0.105 Uiso 1 1 calc R . . H41C H 0.4682 0.1002 -0.0443 0.105 Uiso 1 1 calc R . . C42 C 0.6012(9) 0.0924(8) 0.0604(7) 0.047(4) Uani 1 1 d . . . H42A H 0.5742 0.0506 0.0089 0.057 Uiso 1 1 calc R . . H42B H 0.6530 0.0708 0.0758 0.057 Uiso 1 1 calc R . . C43 C 0.5310(9) 0.0989(8) 0.1198(7) 0.051(4) Uani 1 1 d . . . H43A H 0.5569 0.1395 0.1714 0.077 Uiso 1 1 calc R . . H43B H 0.5130 0.0439 0.1224 0.077 Uiso 1 1 calc R . . H43C H 0.4777 0.1174 0.1039 0.077 Uiso 1 1 calc R . . C44 C 0.8332(8) 0.3083(8) 0.3111(7) 0.042(3) Uani 1 1 d . . . C45 C 0.8137(8) 0.2309(8) 0.3345(7) 0.045(4) Uani 1 1 d . . . H45A H 0.8271 0.1810 0.2904 0.054 Uiso 1 1 calc R . . H45B H 0.8564 0.2404 0.3797 0.054 Uiso 1 1 calc R . . C46 C 0.7187(8) 0.2113(8) 0.3556(7) 0.051(4) Uani 1 1 d . . . H46A H 0.7048 0.2595 0.4002 0.077 Uiso 1 1 calc R . . H46B H 0.7139 0.1622 0.3697 0.077 Uiso 1 1 calc R . . H46C H 0.6756 0.1993 0.3107 0.077 Uiso 1 1 calc R . . C47 C 0.8222(8) 0.3900(8) 0.3812(6) 0.041(3) Uani 1 1 d . . . H47A H 0.8325 0.4377 0.3643 0.050 Uiso 1 1 calc R . . H47B H 0.7592 0.3851 0.3964 0.050 Uiso 1 1 calc R . . C48 C 0.8870(9) 0.4089(8) 0.4523(7) 0.053(4) Uani 1 1 d . . . H48A H 0.8696 0.3678 0.4757 0.080 Uiso 1 1 calc R . . H48B H 0.8842 0.4653 0.4908 0.080 Uiso 1 1 calc R . . H48C H 0.9489 0.4057 0.4362 0.080 Uiso 1 1 calc R . . C49 C 0.7380(7) 0.9787(8) 0.5991(7) 0.032(3) Uani 1 1 d . . . C50 C 0.7112(8) 1.0226(8) 0.6709(7) 0.039(3) Uani 1 1 d . . . H50 H 0.7139 1.0817 0.6944 0.047 Uiso 1 1 calc R . . C51 C 0.6786(8) 0.9641(8) 0.7042(7) 0.036(3) Uani 1 1 d . . . H51 H 0.6548 0.9760 0.7538 0.044 Uiso 1 1 calc R . . C52 C 0.6884(8) 0.8882(8) 0.6508(7) 0.034(3) Uani 1 1 d . . . C53 C 0.5053(8) 0.7991(8) 0.3404(7) 0.041(3) Uani 1 1 d . . . C54 C 0.4107(8) 0.7908(8) 0.3370(7) 0.040(3) Uani 1 1 d . . . H54 H 0.3740 0.8216 0.3196 0.048 Uiso 1 1 calc R . . C55 C 0.3819(8) 0.7290(8) 0.3639(7) 0.039(3) Uani 1 1 d . . . H55 H 0.3207 0.7085 0.3682 0.046 Uiso 1 1 calc R . . C56 C 0.4583(8) 0.7020(7) 0.3838(7) 0.037(3) Uani 1 1 d . . . C57 C 0.6595(8) 0.8758(7) 0.3515(7) 0.032(3) Uani 1 1 d . . . C58 C 0.7454(7) 0.8559(7) 0.3343(7) 0.031(3) Uani 1 1 d . . . H58 H 0.7614 0.8184 0.2857 0.037 Uiso 1 1 calc R . . C59 C 0.8047(8) 0.9016(7) 0.4021(7) 0.035(3) Uani 1 1 d . . . H59 H 0.8677 0.8994 0.4068 0.042 Uiso 1 1 calc R . . C60 C 0.7568(7) 0.9495(7) 0.4599(6) 0.027(3) Uani 1 1 d . . . C61 C 0.5913(7) 0.9731(7) 0.4724(7) 0.037(3) Uani 1 1 d . . . H61A H 0.5907 1.0258 0.4653 0.056 Uiso 1 1 calc R . . H61B H 0.6009 0.9847 0.5282 0.056 Uiso 1 1 calc R . . H61C H 0.5331 0.9363 0.4513 0.056 Uiso 1 1 calc R . . C62 C 0.6465(8) 0.7369(7) 0.5792(7) 0.034(3) Uani 1 1 d . . . C63 C 0.6868(7) 0.6711(7) 0.5340(7) 0.032(3) Uani 1 1 d . . . H63 H 0.7443 0.6595 0.5461 0.038 Uiso 1 1 calc R . . C64 C 0.6264(8) 0.6218(7) 0.4642(7) 0.033(3) Uani 1 1 d . . . H64 H 0.6371 0.5719 0.4232 0.039 Uiso 1 1 calc R . . C65 C 0.5520(8) 0.6597(7) 0.4680(7) 0.032(3) Uani 1 1 d . . . C66 C 0.4975(8) 0.7885(8) 0.5660(7) 0.046(3) Uani 1 1 d . . . H66A H 0.4640 0.7912 0.5213 0.069 Uiso 1 1 calc R . . H66B H 0.5293 0.8446 0.5989 0.069 Uiso 1 1 calc R . . H66C H 0.4549 0.7682 0.5968 0.069 Uiso 1 1 calc R . . C67 C 0.7880(8) 1.0099(7) 0.5442(7) 0.034(3) Uani 1 1 d . . . C68 C 0.7750(8) 1.0988(7) 0.5556(6) 0.036(3) Uani 1 1 d . . . H68A H 0.7093 1.1015 0.5564 0.044 Uiso 1 1 calc R . . H68B H 0.8040 1.1375 0.6076 0.044 Uiso 1 1 calc R . . C69 C 0.8119(10) 1.1310(8) 0.4956(8) 0.060(4) Uani 1 1 d . . . H69A H 0.8781 1.1359 0.4986 0.090 Uiso 1 1 calc R . . H69B H 0.7947 1.1862 0.5060 0.090 Uiso 1 1 calc R . . H69C H 0.7867 1.0919 0.4432 0.090 Uiso 1 1 calc R . . C70 C 0.8917(8) 1.0075(8) 0.5575(7) 0.042(3) Uani 1 1 d . . . H70A H 0.9003 0.9483 0.5411 0.050 Uiso 1 1 calc R . . H70B H 0.9255 1.0307 0.5230 0.050 Uiso 1 1 calc R . . C71 C 0.9328(8) 1.0550(9) 0.6404(7) 0.059(4) Uani 1 1 d . . . H71A H 0.9277 1.1145 0.6566 0.088 Uiso 1 1 calc R . . H71B H 0.9968 1.0490 0.6431 0.088 Uiso 1 1 calc R . . H71C H 0.9005 1.0324 0.6753 0.088 Uiso 1 1 calc R . . C72 C 0.5686(8) 0.8448(7) 0.3032(6) 0.034(3) Uani 1 1 d . . . C73 C 0.5299(8) 0.9174(8) 0.2896(8) 0.045(4) Uani 1 1 d . . . H73 H 0.4678 0.9232 0.2944 0.054 Uiso 1 1 calc R . . C74 C 0.5950(9) 0.9768(8) 0.2689(8) 0.057(4) Uani 1 1 d . . . H74A H 0.6477 0.9984 0.3073 0.086 Uiso 1 1 calc R . . H74B H 0.5654 1.0235 0.2690 0.086 Uiso 1 1 calc R . . H74C H 0.6147 0.9476 0.2167 0.086 Uiso 1 1 calc R . . C75 C 0.5870(8) 0.7774(7) 0.2210(7) 0.043(3) Uani 1 1 d . . . H75A H 0.6224 0.8069 0.1921 0.051 Uiso 1 1 calc R . . H75B H 0.6247 0.7393 0.2304 0.051 Uiso 1 1 calc R . . C76 C 0.5009(8) 0.7242(7) 0.1690(7) 0.046(3) Uani 1 1 d . . . H76A H 0.4644 0.6956 0.1974 0.068 Uiso 1 1 calc R . . H76B H 0.5184 0.6824 0.1209 0.068 Uiso 1 1 calc R . . H76C H 0.4654 0.7607 0.1556 0.068 Uiso 1 1 calc R . . C77 C 0.4688(7) 0.6308(7) 0.4101(7) 0.032(3) Uani 1 1 d . . . C78 C 0.3847(8) 0.6098(8) 0.4466(7) 0.046(4) Uani 1 1 d . . . H78A H 0.3325 0.5925 0.4070 0.055 Uiso 1 1 calc R . . H78B H 0.3739 0.6614 0.4900 0.055 Uiso 1 1 calc R . . C79 C 0.3858(8) 0.5410(8) 0.4786(8) 0.055(4) Uani 1 1 d . . . H79A H 0.3919 0.4882 0.4356 0.083 Uiso 1 1 calc R . . H79B H 0.3291 0.5339 0.5026 0.083 Uiso 1 1 calc R . . H79C H 0.4371 0.5569 0.5179 0.083 Uiso 1 1 calc R . . C80 C 0.4862(7) 0.5543(7) 0.3384(7) 0.038(3) Uani 1 1 d . . . H80A H 0.5409 0.5713 0.3154 0.045 Uiso 1 1 calc R . . H80B H 0.4996 0.5104 0.3566 0.045 Uiso 1 1 calc R . . C81 C 0.4095(8) 0.5163(8) 0.2746(7) 0.051(4) Uani 1 1 d . . . H81A H 0.3577 0.4910 0.2940 0.077 Uiso 1 1 calc R . . H81B H 0.4297 0.4731 0.2291 0.077 Uiso 1 1 calc R . . H81C H 0.3913 0.5601 0.2593 0.077 Uiso 1 1 calc R . . C82 C 0.6763(7) 0.8040(7) 0.6583(7) 0.031(3) Uani 1 1 d . . . C83 C 0.6078(8) 0.7981(8) 0.7171(7) 0.044(3) Uani 1 1 d . . . H83A H 0.6319 0.8398 0.7696 0.053 Uiso 1 1 calc R . . H83B H 0.5511 0.8145 0.7033 0.053 Uiso 1 1 calc R . . C84 C 0.5844(11) 0.7141(9) 0.7227(9) 0.081(5) Uani 1 1 d . . . H84A H 0.5582 0.6723 0.6717 0.121 Uiso 1 1 calc R . . H84B H 0.5403 0.7177 0.7619 0.121 Uiso 1 1 calc R . . H84C H 0.6394 0.6976 0.7382 0.121 Uiso 1 1 calc R . . C85 C 0.7689(7) 0.7884(7) 0.6836(7) 0.037(3) Uani 1 1 d . . . H85A H 0.7615 0.7320 0.6853 0.045 Uiso 1 1 calc R . . H85B H 0.8119 0.7893 0.6439 0.045 Uiso 1 1 calc R . . C86 C 0.8089(9) 0.8535(8) 0.7636(8) 0.060(4) Uani 1 1 d . . . H86A H 0.8198 0.9091 0.7615 0.091 Uiso 1 1 calc R . . H86B H 0.8662 0.8394 0.7776 0.091 Uiso 1 1 calc R . . H86C H 0.7662 0.8535 0.8032 0.091 Uiso 1 1 calc R . . C87 C 0.949(3) 0.019(3) 0.229(2) 0.098(7) Uiso 0.35 1 d PD A 1 H87A H 0.9938 -0.0133 0.2374 0.147 Uiso 0.35 1 calc PR A 1 H87B H 0.9369 0.0608 0.2788 0.147 Uiso 0.35 1 calc PR A 1 H87C H 0.9717 0.0464 0.1942 0.147 Uiso 0.35 1 calc PR A 1 C88 C 0.864(3) -0.039(3) 0.1914(19) 0.098(7) Uiso 0.35 1 d PD A 1 H88A H 0.8117 -0.0090 0.2093 0.117 Uiso 0.35 1 calc PR A 1 H88B H 0.8578 -0.0863 0.2091 0.117 Uiso 0.35 1 calc PR A 1 C89 C 0.858(2) -0.073(3) 0.1047(19) 0.098(7) Uiso 0.35 1 d PD A 1 H89A H 0.8774 -0.0274 0.0870 0.117 Uiso 0.35 1 calc PR A 1 H89B H 0.9010 -0.1143 0.0861 0.117 Uiso 0.35 1 calc PR A 1 C90 C 0.768(3) -0.114(3) 0.0706(19) 0.098(7) Uiso 0.35 1 d PD A 1 H90A H 0.7250 -0.0753 0.0955 0.117 Uiso 0.35 1 calc PR A 1 H90B H 0.7525 -0.1640 0.0840 0.117 Uiso 0.35 1 calc PR A 1 C91 C 0.753(3) -0.141(3) -0.015(2) 0.098(7) Uiso 0.35 1 d PD A 1 H91A H 0.8118 -0.1407 -0.0386 0.117 Uiso 0.35 1 calc PR A 1 H91B H 0.7181 -0.1036 -0.0279 0.117 Uiso 0.35 1 calc PR A 1 C92 C 0.701(3) -0.228(2) -0.045(2) 0.098(7) Uiso 0.35 1 d PD A 1 H92A H 0.7124 -0.2547 -0.0082 0.147 Uiso 0.35 1 calc PR A 1 H92B H 0.7212 -0.2610 -0.0961 0.147 Uiso 0.35 1 calc PR A 1 H92C H 0.6364 -0.2262 -0.0502 0.147 Uiso 0.35 1 calc PR A 1 C88A C 0.939(4) -0.010(4) 0.145(3) 0.033(8) Uiso 0.15 1 d PD B 2 H88C H 0.8916 0.0151 0.1791 0.040 Uiso 0.15 1 calc PR B 2 H88D H 0.9421 -0.0649 0.1472 0.040 Uiso 0.15 1 calc PR B 2 C89A C 0.911(3) -0.023(4) 0.061(3) 0.033(8) Uiso 0.15 1 d PD B 2 H89C H 0.9098 0.0320 0.0563 0.040 Uiso 0.15 1 calc PR B 2 H89D H 0.9535 -0.0527 0.0244 0.040 Uiso 0.15 1 calc PR B 2 C90A C 0.816(3) -0.074(4) 0.041(3) 0.033(8) Uiso 0.15 1 d PD B 2 H90C H 0.8100 -0.1161 -0.0134 0.040 Uiso 0.15 1 calc PR B 2 H90D H 0.7697 -0.0375 0.0470 0.040 Uiso 0.15 1 calc PR B 2 C91A C 0.804(4) -0.119(3) 0.099(3) 0.033(8) Uiso 0.15 1 d PD B 2 H91C H 0.8629 -0.1241 0.1200 0.040 Uiso 0.15 1 calc PR B 2 H91D H 0.7685 -0.0890 0.1426 0.040 Uiso 0.15 1 calc PR B 2 C92A C 0.751(5) -0.204(3) 0.045(4) 0.033(8) Uiso 0.15 1 d PD B 2 H92D H 0.7097 -0.1972 0.0076 0.050 Uiso 0.15 1 calc PR B 2 H92E H 0.7162 -0.2298 0.0770 0.050 Uiso 0.15 1 calc PR B 2 H92F H 0.7938 -0.2411 0.0172 0.050 Uiso 0.15 1 calc PR B 2 C87A C 1.029(4) 0.046(4) 0.177(4) 0.033(8) Uiso 0.15 1 d PD B 2 H87D H 1.0498 0.0716 0.1399 0.050 Uiso 0.15 1 calc PR B 2 H87E H 1.0734 0.0130 0.1838 0.050 Uiso 0.15 1 calc PR B 2 H87F H 1.0220 0.0906 0.2272 0.050 Uiso 0.15 1 calc PR B 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 Sm1 0.0338(4) 0.0331(5) 0.0274(4) 0.0079(3) -0.0021(3) 0.0030(3) Sm2 0.0294(4) 0.0294(4) 0.0297(4) 0.0093(3) 0.0010(3) 0.0055(3) P1 0.041(2) 0.034(2) 0.033(2) 0.0061(17) 0.0016(16) 0.0090(16) P2 0.0359(19) 0.035(2) 0.0320(19) 0.0096(16) 0.0012(15) 0.0097(15) N1 0.041(7) 0.033(6) 0.029(6) 0.014(5) 0.005(5) 0.006(5) N2 0.036(6) 0.045(7) 0.029(6) 0.009(5) -0.002(5) 0.001(5) N3 0.035(6) 0.035(7) 0.020(5) -0.001(5) 0.004(5) 0.012(5) N4 0.043(6) 0.025(6) 0.029(6) 0.006(5) -0.004(5) 0.004(5) N5 0.022(5) 0.030(6) 0.026(6) 0.003(5) -0.001(4) -0.001(4) N6 0.032(6) 0.032(6) 0.031(6) 0.012(5) -0.011(5) 0.005(5) N7 0.027(6) 0.024(6) 0.035(6) 0.013(5) -0.005(5) 0.005(4) N8 0.025(6) 0.031(6) 0.036(6) 0.009(5) 0.007(5) 0.000(5) C1 0.031(7) 0.052(9) 0.040(8) 0.024(7) 0.006(6) 0.005(6) C2 0.038(7) 0.037(8) 0.027(7) 0.013(6) -0.001(6) 0.009(6) C3 0.045(8) 0.054(10) 0.056(10) 0.019(8) 0.003(7) 0.012(7) C4 0.029(7) 0.066(10) 0.066(10) 0.029(9) 0.010(7) 0.020(7) C5 0.041(8) 0.047(9) 0.036(8) 0.013(7) -0.001(6) 0.011(6) C6 0.039(7) 0.023(7) 0.025(7) 0.010(6) 0.011(6) 0.007(6) C7 0.032(7) 0.028(7) 0.036(7) 0.014(6) -0.004(6) 0.009(6) C8 0.040(8) 0.054(10) 0.032(8) 0.012(7) -0.012(6) 0.004(7) C9 0.029(7) 0.055(9) 0.056(9) 0.029(8) 0.010(6) 0.018(6) C10 0.044(8) 0.045(9) 0.047(9) 0.003(7) -0.001(7) 0.011(7) C11 0.047(8) 0.037(8) 0.017(7) 0.000(6) -0.007(6) 0.010(6) C12 0.028(7) 0.082(11) 0.054(9) 0.043(9) -0.011(7) 0.003(7) C13 0.053(9) 0.076(11) 0.037(8) 0.038(8) 0.003(7) 0.031(8) C14 0.033(7) 0.028(8) 0.045(8) 0.013(7) 0.011(6) 0.009(6) C15 0.039(8) 0.039(9) 0.032(8) 0.006(7) -0.004(6) 0.017(7) C16 0.067(10) 0.043(10) 0.029(8) 0.002(8) -0.005(7) 0.009(8) C17 0.073(10) 0.033(9) 0.031(8) 0.005(7) -0.004(7) -0.012(7) C18 0.038(8) 0.027(8) 0.039(8) 0.014(7) -0.001(6) -0.006(6) C19 0.034(7) 0.048(9) 0.020(7) 0.008(7) 0.004(6) -0.003(6) C20 0.025(6) 0.022(7) 0.024(7) -0.001(6) 0.001(5) 0.004(5) C21 0.031(7) 0.022(8) 0.045(8) 0.016(7) -0.005(6) -0.005(6) C22 0.029(7) 0.039(8) 0.021(6) 0.014(6) -0.002(5) 0.005(6) C23 0.045(8) 0.043(9) 0.023(7) 0.005(6) 0.000(6) 0.006(7) C24 0.036(8) 0.061(10) 0.030(8) 0.024(8) 0.003(6) -0.008(7) C25 0.030(7) 0.031(8) 0.036(8) 0.013(7) 0.010(6) 0.000(6) C26 0.039(8) 0.051(10) 0.038(8) 0.017(8) -0.002(7) 0.003(7) C27 0.037(7) 0.026(8) 0.036(8) 0.013(7) -0.007(6) -0.013(6) C28 0.068(10) 0.037(9) 0.032(8) 0.002(7) -0.009(7) 0.011(7) C29 0.046(8) 0.036(8) 0.019(7) 0.006(6) 0.000(6) 0.001(6) C30 0.031(7) 0.052(9) 0.032(7) 0.018(7) 0.005(6) 0.010(6) C31 0.052(9) 0.093(13) 0.049(9) 0.036(9) 0.000(7) 0.003(8) C32 0.032(7) 0.040(8) 0.034(7) 0.011(7) 0.004(6) -0.003(6) C33 0.036(7) 0.061(10) 0.038(8) -0.001(7) -0.010(6) 0.016(7) C34 0.040(7) 0.020(7) 0.041(8) 0.001(6) -0.011(6) -0.009(6) C35 0.045(8) 0.041(9) 0.031(7) -0.001(7) 0.002(6) 0.008(7) C36 0.059(9) 0.052(10) 0.041(9) 0.000(7) 0.011(7) 0.006(8) C37 0.034(7) 0.053(9) 0.024(7) 0.006(7) -0.004(6) 0.006(6) C38 0.080(11) 0.059(10) 0.039(9) 0.012(8) -0.029(8) 0.007(8) C39 0.038(8) 0.042(9) 0.035(8) 0.013(7) 0.000(7) -0.011(6) C40 0.028(7) 0.047(9) 0.045(8) 0.020(7) -0.015(6) -0.011(6) C41 0.076(11) 0.076(12) 0.058(10) 0.037(9) -0.035(8) -0.017(9) C42 0.063(9) 0.040(9) 0.027(7) 0.009(7) -0.008(7) -0.016(7) C43 0.066(10) 0.041(9) 0.037(8) 0.011(7) -0.004(7) -0.007(7) C44 0.034(8) 0.058(10) 0.034(8) 0.025(8) 0.001(6) -0.009(7) C45 0.044(8) 0.057(9) 0.032(8) 0.017(7) -0.011(6) 0.003(7) C46 0.058(9) 0.047(9) 0.045(9) 0.021(7) -0.005(7) -0.013(7) C47 0.043(8) 0.054(9) 0.023(7) 0.015(7) 0.002(6) -0.001(7) C48 0.068(10) 0.057(10) 0.026(7) 0.006(7) -0.011(7) 0.007(8) C49 0.024(7) 0.039(9) 0.035(8) 0.019(7) -0.006(6) -0.002(6) C50 0.041(8) 0.027(8) 0.033(8) -0.009(7) 0.008(6) 0.014(6) C51 0.041(8) 0.044(9) 0.029(7) 0.019(7) 0.013(6) 0.006(6) C52 0.038(7) 0.030(8) 0.028(7) 0.009(7) -0.004(6) -0.003(6) C53 0.043(8) 0.039(8) 0.041(8) 0.019(7) -0.002(7) -0.003(6) C54 0.033(8) 0.035(8) 0.059(9) 0.026(7) -0.002(7) 0.010(6) C55 0.019(7) 0.045(9) 0.046(8) 0.010(7) -0.001(6) 0.008(6) C56 0.033(7) 0.032(8) 0.042(8) 0.014(7) 0.005(6) -0.007(6) C57 0.045(8) 0.030(7) 0.028(7) 0.015(6) 0.008(6) 0.013(6) C58 0.034(7) 0.035(8) 0.038(8) 0.024(7) 0.009(6) 0.021(6) C59 0.025(7) 0.043(8) 0.038(8) 0.021(7) -0.011(6) -0.006(6) C60 0.032(7) 0.023(7) 0.024(7) 0.008(6) 0.006(6) 0.005(6) C61 0.043(8) 0.031(8) 0.044(8) 0.014(6) 0.015(6) 0.026(6) C62 0.040(8) 0.024(8) 0.035(8) 0.010(6) 0.005(6) 0.001(6) C63 0.027(7) 0.032(8) 0.036(7) 0.016(7) -0.013(6) -0.006(6) C64 0.045(8) 0.018(7) 0.036(8) 0.011(6) 0.011(6) 0.005(6) C65 0.042(8) 0.030(8) 0.033(8) 0.019(7) 0.020(6) 0.011(6) C66 0.039(8) 0.040(8) 0.042(8) -0.003(7) 0.002(6) 0.008(7) C67 0.036(7) 0.022(7) 0.041(8) 0.008(6) 0.004(6) 0.004(6) C68 0.045(8) 0.032(8) 0.030(7) 0.010(6) -0.011(6) 0.006(6) C69 0.082(11) 0.037(9) 0.053(10) 0.013(8) -0.001(8) -0.001(8) C70 0.039(8) 0.043(9) 0.036(8) 0.011(7) 0.010(6) -0.003(6) C71 0.035(8) 0.072(11) 0.052(9) 0.009(8) 0.012(7) -0.008(7) C72 0.049(8) 0.026(7) 0.022(7) 0.002(6) -0.001(6) 0.007(6) C73 0.036(7) 0.041(9) 0.078(10) 0.041(8) -0.003(7) 0.013(6) C74 0.066(10) 0.043(9) 0.055(9) 0.016(8) -0.022(8) -0.003(8) C75 0.057(9) 0.031(8) 0.047(8) 0.021(7) -0.003(7) 0.011(6) C76 0.061(9) 0.028(8) 0.033(8) -0.003(6) -0.012(7) 0.005(7) C77 0.016(6) 0.042(8) 0.036(7) 0.018(7) 0.009(6) -0.005(6) C78 0.060(9) 0.034(8) 0.037(8) 0.011(7) -0.007(7) -0.004(7) C79 0.044(8) 0.063(10) 0.055(10) 0.020(8) 0.005(7) 0.005(7) C80 0.034(7) 0.031(8) 0.040(8) 0.009(7) 0.001(6) -0.006(6) C81 0.037(8) 0.050(9) 0.054(9) 0.012(8) -0.010(7) -0.007(7) C82 0.037(7) 0.026(7) 0.031(7) 0.010(6) 0.009(6) 0.005(6) C83 0.046(8) 0.052(9) 0.033(8) 0.018(7) -0.006(6) -0.001(7) C84 0.132(15) 0.050(11) 0.063(11) 0.023(9) 0.041(10) 0.015(10) C85 0.039(7) 0.036(8) 0.036(8) 0.014(6) -0.016(6) 0.009(6) C86 0.064(10) 0.056(10) 0.056(10) 0.018(8) -0.024(8) 0.006(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 Sm1 N1 2.510(9) . ? Sm1 N2 2.513(10) . ? Sm1 C1 2.524(12) . ? Sm1 N3 2.780(9) . ? Sm1 N4 2.790(9) . ? Sm1 C19 2.836(11) . ? Sm1 C22 2.863(11) . ? Sm1 C24 2.882(11) . ? Sm1 C27 2.886(11) . ? Sm1 C26 2.907(12) . ? Sm1 C21 2.918(11) . ? Sm1 C20 2.933(11) . ? Sm2 N6 2.479(8) . ? Sm2 N5 2.512(9) . ? Sm2 C6 2.520(11) . ? Sm2 N8 2.790(9) . ? Sm2 N7 2.796(8) . ? Sm2 C65 2.861(11) . ? Sm2 C57 2.888(10) . ? Sm2 C60 2.889(11) . ? Sm2 C62 2.891(11) . ? Sm2 C59 2.926(11) . ? Sm2 C58 2.939(11) . ? Sm2 C64 2.951(10) . ? P1 C1 1.660(12) . ? P1 P2 2.267(5) . ? P2 C6 1.673(11) . ? N1 C11 1.398(14) . ? N1 C14 1.408(14) . ? N2 C15 1.399(15) . ? N2 C18 1.408(14) . ? N3 C19 1.398(14) . ? N3 C22 1.409(12) . ? N3 C23 1.478(14) . ? N4 C24 1.376(15) . ? N4 C27 1.385(13) . ? N4 C28 1.443(14) . ? N5 C52 1.376(14) . ? N5 C49 1.404(14) . ? N6 C53 1.381(13) . ? N6 C56 1.385(13) . ? N7 C60 1.401(13) . ? N7 C57 1.401(14) . ? N7 C61 1.490(13) . ? N8 C65 1.402(14) . ? N8 C62 1.418(13) . ? N8 C66 1.464(14) . ? C1 C2 1.539(15) . ? C2 C5 1.511(15) . ? C2 C3 1.529(16) . ? C2 C4 1.559(16) . ? C6 C7 1.521(14) . ? C7 C9 1.504(15) . ? C7 C10 1.506(15) . ? C7 C8 1.512(15) . ? C11 C12 1.372(15) . ? C11 C29 1.512(16) . ? C12 C13 1.385(16) . ? C13 C14 1.381(15) . ? C14 C44 1.503(16) . ? C15 C16 1.379(16) . ? C15 C34 1.519(16) . ? C16 C17 1.411(17) . ? C17 C18 1.361(16) . ? C18 C39 1.485(17) . ? C19 C20 1.375(15) . ? C19 C29 1.526(14) . ? C20 C21 1.408(14) . ? C21 C22 1.372(15) . ? C22 C34 1.536(15) . ? C24 C25 1.360(16) . ? C24 C44 1.581(15) . ? C25 C26 1.403(15) . ? C26 C27 1.341(16) . ? C27 C39 1.525(16) . ? C29 C32 1.544(16) . ? C29 C30 1.562(16) . ? C30 C31 1.509(16) . ? C32 C33 1.522(14) . ? C34 C35 1.529(16) . ? C34 C37 1.540(15) . ? C35 C36 1.521(16) . ? C37 C38 1.518(15) . ? C39 C42 1.528(16) . ? C39 C40 1.581(16) . ? C40 C41 1.519(16) . ? C42 C43 1.519(17) . ? C44 C47 1.553(17) . ? C44 C45 1.563(16) . ? C45 C46 1.508(16) . ? C47 C48 1.520(14) . ? C49 C50 1.358(15) . ? C49 C67 1.493(15) . ? C50 C51 1.421(16) . ? C51 C52 1.350(16) . ? C52 C82 1.515(15) . ? C53 C54 1.398(15) . ? C53 C72 1.497(16) . ? C54 C55 1.374(16) . ? C55 C56 1.388(15) . ? C56 C77 1.524(15) . ? C57 C58 1.387(15) . ? C57 C72 1.522(15) . ? C58 C59 1.414(15) . ? C59 C60 1.369(15) . ? C60 C67 1.533(15) . ? C62 C63 1.365(16) . ? C62 C82 1.497(16) . ? C63 C64 1.456(14) . ? C64 C65 1.362(15) . ? C65 C77 1.521(15) . ? C67 C68 1.527(15) . ? C67 C70 1.573(15) . ? C68 C69 1.505(16) . ? C70 C71 1.508(15) . ? C72 C73 1.564(15) . ? C72 C75 1.588(16) . ? C73 C74 1.485(16) . ? C75 C76 1.544(15) . ? C77 C78 1.506(15) . ? C77 C80 1.541(16) . ? C78 C79 1.530(16) . ? C80 C81 1.513(14) . ? C82 C83 1.531(16) . ? C82 C85 1.544(14) . ? C83 C84 1.503(17) . ? C85 C86 1.530(15) . ? C87 C88 1.479(19) . ? C88 C89 1.482(19) . ? C89 C90 1.446(19) . ? C90 C91 1.473(19) . ? C91 C92 1.490(19) . ? C88A C87A 1.51(2) . ? C88A C89A 1.53(2) . ? C89A C90A 1.522(19) . ? C90A C91A 1.54(2) . ? C91A C92A 1.54(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Sm1 N2 123.8(3) . . ? N1 Sm1 C1 125.0(3) . . ? N2 Sm1 C1 111.2(3) . . ? N1 Sm1 N3 75.0(3) . . ? N2 Sm1 N3 76.9(3) . . ? C1 Sm1 N3 122.0(3) . . ? N1 Sm1 N4 75.6(3) . . ? N2 Sm1 N4 74.2(3) . . ? C1 Sm1 N4 122.3(3) . . ? N3 Sm1 N4 115.3(3) . . ? N1 Sm1 C19 63.1(3) . . ? N2 Sm1 C19 105.1(3) . . ? C1 Sm1 C19 105.4(4) . . ? N3 Sm1 C19 28.8(3) . . ? N4 Sm1 C19 129.4(3) . . ? N1 Sm1 C22 103.6(3) . . ? N2 Sm1 C22 62.8(3) . . ? C1 Sm1 C22 101.7(3) . . ? N3 Sm1 C22 28.9(3) . . ? N4 Sm1 C22 127.2(3) . . ? C19 Sm1 C22 47.0(3) . . ? N1 Sm1 C24 62.3(3) . . ? N2 Sm1 C24 101.8(4) . . ? C1 Sm1 C24 107.6(4) . . ? N3 Sm1 C24 127.4(3) . . ? N4 Sm1 C24 28.0(3) . . ? C19 Sm1 C24 125.4(3) . . ? C22 Sm1 C24 150.4(4) . . ? N1 Sm1 C27 103.2(3) . . ? N2 Sm1 C27 62.0(3) . . ? C1 Sm1 C27 101.0(4) . . ? N3 Sm1 C27 129.1(3) . . ? N4 Sm1 C27 28.2(3) . . ? C19 Sm1 C27 153.5(4) . . ? C22 Sm1 C27 124.7(3) . . ? C24 Sm1 C27 45.6(3) . . ? N1 Sm1 C26 106.3(3) . . ? N2 Sm1 C26 83.1(3) . . ? C1 Sm1 C26 77.8(4) . . ? N3 Sm1 C26 155.9(3) . . ? N4 Sm1 C26 44.9(3) . . ? C19 Sm1 C26 169.0(3) . . ? C22 Sm1 C26 143.5(3) . . ? C24 Sm1 C26 44.4(3) . . ? C27 Sm1 C26 26.8(3) . . ? N1 Sm1 C21 108.6(3) . . ? N2 Sm1 C21 83.2(3) . . ? C1 Sm1 C21 77.0(4) . . ? N3 Sm1 C21 46.0(3) . . ? N4 Sm1 C21 154.3(3) . . ? C19 Sm1 C21 45.6(3) . . ? C22 Sm1 C21 27.4(3) . . ? C24 Sm1 C21 170.9(3) . . ? C27 Sm1 C21 142.2(3) . . ? C26 Sm1 C21 144.5(3) . . ? N1 Sm1 C20 84.6(3) . . ? N2 Sm1 C20 108.5(3) . . ? C1 Sm1 C20 79.0(3) . . ? N3 Sm1 C20 46.4(3) . . ? N4 Sm1 C20 156.9(3) . . ? C19 Sm1 C20 27.5(3) . . ? C22 Sm1 C20 46.2(3) . . ? C24 Sm1 C20 144.1(3) . . ? C27 Sm1 C20 170.0(3) . . ? C26 Sm1 C20 156.5(4) . . ? C21 Sm1 C20 27.8(3) . . ? N6 Sm2 N5 123.8(3) . . ? N6 Sm2 C6 121.3(3) . . ? N5 Sm2 C6 114.9(3) . . ? N6 Sm2 N8 75.0(3) . . ? N5 Sm2 N8 74.8(3) . . ? C6 Sm2 N8 121.2(3) . . ? N6 Sm2 N7 76.9(3) . . ? N5 Sm2 N7 75.7(3) . . ? C6 Sm2 N7 122.4(3) . . ? N8 Sm2 N7 116.2(3) . . ? N6 Sm2 C65 62.1(3) . . ? N5 Sm2 C65 103.0(3) . . ? C6 Sm2 C65 104.1(3) . . ? N8 Sm2 C65 28.7(3) . . ? N7 Sm2 C65 129.6(3) . . ? N6 Sm2 C57 63.5(3) . . ? N5 Sm2 C57 103.9(3) . . ? C6 Sm2 C57 106.0(3) . . ? N8 Sm2 C57 128.7(3) . . ? N7 Sm2 C57 28.5(3) . . ? C65 Sm2 C57 125.5(3) . . ? N6 Sm2 C60 104.9(3) . . ? N5 Sm2 C60 63.3(3) . . ? C6 Sm2 C60 102.5(3) . . ? N8 Sm2 C60 129.1(3) . . ? N7 Sm2 C60 28.5(3) . . ? C65 Sm2 C60 153.3(3) . . ? C57 Sm2 C60 46.5(3) . . ? N6 Sm2 C62 103.5(3) . . ? N5 Sm2 C62 61.0(3) . . ? C6 Sm2 C62 102.1(3) . . ? N8 Sm2 C62 28.8(3) . . ? N7 Sm2 C62 128.0(3) . . ? C65 Sm2 C62 47.2(3) . . ? C57 Sm2 C62 151.8(3) . . ? C60 Sm2 C62 124.2(3) . . ? N6 Sm2 C59 108.9(3) . . ? N5 Sm2 C59 84.2(3) . . ? C6 Sm2 C59 77.8(4) . . ? N8 Sm2 C59 156.1(3) . . ? N7 Sm2 C59 45.8(3) . . ? C65 Sm2 C59 170.6(3) . . ? C57 Sm2 C59 45.8(3) . . ? C60 Sm2 C59 27.2(3) . . ? C62 Sm2 C59 141.9(3) . . ? N6 Sm2 C58 84.1(3) . . ? N5 Sm2 C58 108.7(3) . . ? C6 Sm2 C58 79.6(3) . . ? N8 Sm2 C58 156.0(3) . . ? N7 Sm2 C58 45.9(3) . . ? C65 Sm2 C58 142.8(3) . . ? C57 Sm2 C58 27.5(3) . . ? C60 Sm2 C58 45.7(3) . . ? C62 Sm2 C58 169.5(3) . . ? C59 Sm2 C58 27.9(3) . . ? N6 Sm2 C64 83.0(3) . . ? N5 Sm2 C64 106.7(3) . . ? C6 Sm2 C64 78.5(3) . . ? N8 Sm2 C64 45.6(3) . . ? N7 Sm2 C64 156.6(3) . . ? C65 Sm2 C64 27.0(3) . . ? C57 Sm2 C64 143.6(3) . . ? C60 Sm2 C64 169.5(3) . . ? C62 Sm2 C64 46.0(3) . . ? C59 Sm2 C64 156.3(4) . . ? C58 Sm2 C64 143.7(3) . . ? C1 P1 P2 116.3(5) . . ? C1 P1 Sm1 59.2(4) . . ? P2 P1 Sm1 165.32(17) . . ? C6 P2 P1 114.8(4) . . ? C6 P2 Sm2 56.9(4) . . ? P1 P2 Sm2 165.41(16) . . ? C11 N1 C14 103.2(9) . . ? C11 N1 Sm1 124.9(7) . . ? C14 N1 Sm1 127.3(7) . . ? C15 N2 C18 105.4(10) . . ? C15 N2 Sm1 124.1(7) . . ? C18 N2 Sm1 126.1(8) . . ? C19 N3 C22 108.0(9) . . ? C19 N3 C23 127.3(9) . . ? C22 N3 C23 124.7(9) . . ? C19 N3 Sm1 77.8(6) . . ? C22 N3 Sm1 78.8(6) . . ? C23 N3 Sm1 111.5(7) . . ? C24 N4 C27 108.0(10) . . ? C24 N4 C28 127.0(10) . . ? C27 N4 C28 124.9(10) . . ? C24 N4 Sm1 79.7(6) . . ? C27 N4 Sm1 79.8(6) . . ? C28 N4 Sm1 110.2(7) . . ? C52 N5 C49 104.3(9) . . ? C52 N5 Sm2 126.7(7) . . ? C49 N5 Sm2 123.3(7) . . ? C53 N6 C56 103.8(9) . . ? C53 N6 Sm2 122.7(7) . . ? C56 N6 Sm2 126.7(7) . . ? C60 N7 C57 109.0(9) . . ? C60 N7 C61 124.9(9) . . ? C57 N7 C61 125.6(9) . . ? C60 N7 Sm2 79.5(5) . . ? C57 N7 Sm2 79.4(6) . . ? C61 N7 Sm2 114.7(6) . . ? C65 N8 C62 109.5(9) . . ? C65 N8 C66 125.4(9) . . ? C62 N8 C66 125.1(10) . . ? C65 N8 Sm2 78.5(6) . . ? C62 N8 Sm2 79.5(6) . . ? C66 N8 Sm2 111.7(7) . . ? C2 C1 P1 132.0(10) . . ? C2 C1 Sm1 141.3(8) . . ? P1 C1 Sm1 86.5(5) . . ? C5 C2 C3 109.1(10) . . ? C5 C2 C1 110.4(9) . . ? C3 C2 C1 110.6(10) . . ? C5 C2 C4 108.6(10) . . ? C3 C2 C4 108.3(10) . . ? C1 C2 C4 109.7(9) . . ? C7 C6 P2 132.8(9) . . ? C7 C6 Sm2 137.8(7) . . ? P2 C6 Sm2 89.3(5) . . ? C9 C7 C10 109.8(10) . . ? C9 C7 C8 109.3(10) . . ? C10 C7 C8 108.3(9) . . ? C9 C7 C6 109.7(9) . . ? C10 C7 C6 110.8(10) . . ? C8 C7 C6 108.9(9) . . ? C12 C11 N1 110.8(11) . . ? C12 C11 C29 130.5(11) . . ? N1 C11 C29 118.4(10) . . ? C11 C12 C13 108.4(11) . . ? C14 C13 C12 106.0(10) . . ? C13 C14 N1 111.6(10) . . ? C13 C14 C44 130.0(11) . . ? N1 C14 C44 117.8(10) . . ? C16 C15 N2 109.3(12) . . ? C16 C15 C34 129.1(12) . . ? N2 C15 C34 120.9(11) . . ? C15 C16 C17 107.9(12) . . ? C18 C17 C16 107.0(11) . . ? C17 C18 N2 110.4(11) . . ? C17 C18 C39 130.1(12) . . ? N2 C18 C39 119.4(11) . . ? C20 C19 N3 108.8(9) . . ? C20 C19 C29 128.5(11) . . ? N3 C19 C29 122.7(11) . . ? C20 C19 Sm1 80.2(7) . . ? N3 C19 Sm1 73.4(6) . . ? C29 C19 Sm1 114.3(7) . . ? C19 C20 C21 106.7(10) . . ? C19 C20 Sm1 72.3(6) . . ? C21 C20 Sm1 75.5(6) . . ? C22 C21 C20 110.0(10) . . ? C22 C21 Sm1 74.1(6) . . ? C20 C21 Sm1 76.7(6) . . ? C21 C22 N3 106.6(9) . . ? C21 C22 C34 129.4(10) . . ? N3 C22 C34 124.1(10) . . ? C21 C22 Sm1 78.5(7) . . ? N3 C22 Sm1 72.3(6) . . ? C34 C22 Sm1 115.8(7) . . ? C25 C24 N4 109.7(10) . . ? C25 C24 C44 128.2(12) . . ? N4 C24 C44 122.1(12) . . ? C25 C24 Sm1 79.7(7) . . ? N4 C24 Sm1 72.3(6) . . ? C44 C24 Sm1 114.1(7) . . ? C24 C25 C26 104.6(12) . . ? C24 C25 Sm1 73.4(7) . . ? C26 C25 Sm1 74.1(7) . . ? C27 C26 C25 111.2(11) . . ? C27 C26 Sm1 75.7(7) . . ? C25 C26 Sm1 78.3(7) . . ? C26 C27 N4 106.2(10) . . ? C26 C27 C39 130.8(11) . . ? N4 C27 C39 123.0(12) . . ? C26 C27 Sm1 77.5(7) . . ? N4 C27 Sm1 72.0(6) . . ? C39 C27 Sm1 114.5(7) . . ? C11 C29 C19 109.0(9) . . ? C11 C29 C32 107.9(9) . . ? C19 C29 C32 107.7(10) . . ? C11 C29 C30 110.8(10) . . ? C19 C29 C30 111.2(9) . . ? C32 C29 C30 110.1(9) . . ? C31 C30 C29 115.1(10) . . ? C33 C32 C29 114.9(10) . . ? C15 C34 C35 110.6(10) . . ? C15 C34 C22 107.2(10) . . ? C35 C34 C22 112.3(9) . . ? C15 C34 C37 109.3(9) . . ? C35 C34 C37 111.3(10) . . ? C22 C34 C37 105.9(9) . . ? C36 C35 C34 114.6(10) . . ? C38 C37 C34 115.2(10) . . ? C18 C39 C27 109.3(10) . . ? C18 C39 C42 113.5(11) . . ? C27 C39 C42 107.9(9) . . ? C18 C39 C40 109.0(10) . . ? C27 C39 C40 107.2(10) . . ? C42 C39 C40 109.7(9) . . ? C41 C40 C39 113.2(11) . . ? C43 C42 C39 115.7(11) . . ? C14 C44 C47 109.8(10) . . ? C14 C44 C45 112.6(11) . . ? C47 C44 C45 110.5(10) . . ? C14 C44 C24 109.4(10) . . ? C47 C44 C24 105.5(10) . . ? C45 C44 C24 108.8(9) . . ? C46 C45 C44 116.1(10) . . ? C48 C47 C44 113.5(10) . . ? C50 C49 N5 109.9(10) . . ? C50 C49 C67 129.4(12) . . ? N5 C49 C67 120.4(11) . . ? C49 C50 C51 107.5(11) . . ? C52 C51 C50 105.7(11) . . ? C51 C52 N5 112.3(10) . . ? C51 C52 C82 129.3(11) . . ? N5 C52 C82 118.2(11) . . ? N6 C53 C54 111.7(10) . . ? N6 C53 C72 120.2(10) . . ? C54 C53 C72 127.3(11) . . ? C55 C54 C53 105.9(10) . . ? C54 C55 C56 107.6(11) . . ? N6 C56 C55 110.9(10) . . ? N6 C56 C77 117.3(10) . . ? C55 C56 C77 131.6(11) . . ? C58 C57 N7 107.0(10) . . ? C58 C57 C72 131.8(11) . . ? N7 C57 C72 121.1(10) . . ? C58 C57 Sm2 78.3(6) . . ? N7 C57 Sm2 72.1(5) . . ? C72 C57 Sm2 112.2(7) . . ? C57 C58 C59 107.7(11) . . ? C57 C58 Sm2 74.2(6) . . ? C59 C58 Sm2 75.6(6) . . ? C60 C59 C58 108.9(10) . . ? C60 C59 Sm2 74.9(7) . . ? C58 C59 Sm2 76.5(6) . . ? C59 C60 N7 107.1(9) . . ? C59 C60 C67 130.3(10) . . ? N7 C60 C67 122.5(10) . . ? C59 C60 Sm2 77.9(7) . . ? N7 C60 Sm2 72.0(5) . . ? C67 C60 Sm2 113.1(7) . . ? C63 C62 N8 106.9(10) . . ? C63 C62 C82 130.5(11) . . ? N8 C62 C82 122.6(11) . . ? C63 C62 Sm2 79.1(7) . . ? N8 C62 Sm2 71.6(6) . . ? C82 C62 Sm2 115.9(7) . . ? C62 C63 C64 108.0(10) . . ? C62 C63 Sm2 73.9(7) . . ? C64 C63 Sm2 75.6(6) . . ? C65 C64 C63 108.1(11) . . ? C65 C64 Sm2 72.8(6) . . ? C63 C64 Sm2 75.8(6) . . ? C64 C65 N8 107.5(10) . . ? C64 C65 C77 127.9(11) . . ? N8 C65 C77 124.6(10) . . ? C64 C65 Sm2 80.2(7) . . ? N8 C65 Sm2 72.8(6) . . ? C77 C65 Sm2 114.5(7) . . ? C49 C67 C68 113.0(10) . . ? C49 C67 C60 108.9(9) . . ? C68 C67 C60 110.0(9) . . ? C49 C67 C70 108.1(9) . . ? C68 C67 C70 109.4(9) . . ? C60 C67 C70 107.2(9) . . ? C69 C68 C67 116.7(11) . . ? C71 C70 C67 115.4(10) . . ? C53 C72 C57 109.1(9) . . ? C53 C72 C73 113.8(10) . . ? C57 C72 C73 111.8(9) . . ? C53 C72 C75 106.6(10) . . ? C57 C72 C75 106.2(9) . . ? C73 C72 C75 108.9(9) . . ? C74 C73 C72 116.9(10) . . ? C76 C75 C72 114.8(10) . . ? C78 C77 C65 111.4(9) . . ? C78 C77 C56 109.8(10) . . ? C65 C77 C56 107.4(9) . . ? C78 C77 C80 111.0(9) . . ? C65 C77 C80 108.4(9) . . ? C56 C77 C80 108.6(9) . . ? C77 C78 C79 116.2(11) . . ? C81 C80 C77 115.7(10) . . ? C62 C82 C52 108.4(9) . . ? C62 C82 C83 110.1(9) . . ? C52 C82 C83 112.8(10) . . ? C62 C82 C85 106.9(10) . . ? C52 C82 C85 109.1(9) . . ? C83 C82 C85 109.4(9) . . ? C84 C83 C82 116.6(11) . . ? C86 C85 C82 113.0(10) . . ? C87 C88 C89 114(3) . . ? C90 C89 C88 112(2) . . ? C89 C90 C91 116(3) . . ? C90 C91 C92 107(2) . . ? C87A C88A C89A 114(3) . . ? C90A C89A C88A 106(2) . . ? C89A C90A C91A 107(2) . . ? C92A C91A C90A 101(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.184 _refine_diff_density_min -0.810 _refine_diff_density_rms 0.150