Supplementary Material (ESI) for Chemical Communications This journal is (C) The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Doedens, Robert J.' 'Evans, William J.' 'Perotti, Jeremy M.' 'Ziller, Joseph W.' _publ_contact_author_name 'Dr William J Evans' _publ_contact_author_address ; Department of Chemistry University of California Irvine CA 92697- 2025 UNITED STATES OF AMERICA ; _publ_contact_author_email 'wevans@uci.edu' _publ_section_title ; The Tetramethylpiperidinyl-1-oxide Anion (TMPO-) as a Ligand in Lanthanide Chemistry: Synthesis of the Per(TMPO-) Complex [(ONC5H6Me4)2Sm(u-ONC5H6Me4)]2 ; data_jp2a _database_code_CSD 170799 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H54 N3 O3 Sm' _chemical_formula_weight 619.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sm' 'Sm' -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3838(11) _cell_length_b 11.9579(13) _cell_length_c 12.8023(14) _cell_angle_alpha 85.934(2) _cell_angle_beta 83.450(2) _cell_angle_gamma 66.8500(10) _cell_volume 1451.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used 5769 _cell_measurement_theta_min 4.45 _cell_measurement_theta_max 56.52 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 646 _exptl_absorpt_coefficient_mu 2.053 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.7730 _exptl_absorpt_correction_T_max 0.6034 _exptl_absorpt_process_details 'computed via sadabs' _exptl_special_details ; Crystal orientation and preliminary unit cell constants were obtained from reflections gathered from three sets of 15 frames each, chosen to cover a wide range of reciprocal space. Refined cell parameters were computed after data collection on the basis of the setting angles of 5769 reflections with a resolution limit of 0.75 Angstroms. ; _diffrn_ambient_temperature 163(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '30s frames at 0.3 deg. omega increments' _diffrn_detector_area_resol_mean ? _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% none _diffrn_reflns_number 15802 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 28.31 _diffrn_special_details ; A full sphere of data was collected by use of 0.3 degree omega increments and 30s frame counting times. The first 50 frames were remeasured at the end of data collection and no evidence of decay was observed. To a limiting resolution of 0.75 A, the completeness of coverage was 90.42%, the average redundancy was 2.3, and R(sym) for the uncorrected data was 0.076. ; _reflns_number_total 6872 _reflns_number_gt 6279 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Hydrogen atoms were included at idealized positions and refined by use of the riding model. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.05P)^2^+30.0P] 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 n/a _refine_ls_number_reflns 6872 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1655 _refine_ls_wR_factor_gt 0.1621 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 0.08539(4) 0.00680(3) -0.13404(3) 0.01224(11) Uani 1 1 d . . . O1 O 0.1290(5) -0.0224(5) 0.0396(3) 0.0125(9) Uani 1 1 d . . . O2 O 0.1011(6) 0.1705(5) -0.1973(4) 0.0223(11) Uani 1 1 d . . . O3 O 0.2322(6) -0.1462(5) -0.2146(4) 0.0213(11) Uani 1 1 d . . . N1 N 0.1527(6) 0.0035(5) 0.1417(4) 0.0136(11) Uani 1 1 d . . . N2 N 0.0744(7) 0.2644(6) -0.2777(5) 0.0195(13) Uani 1 1 d . . . N3 N 0.3010(7) -0.2685(6) -0.2487(5) 0.0188(12) Uani 1 1 d . . . C1 C 0.2689(8) -0.1019(7) 0.1885(6) 0.0210(15) Uani 1 1 d . . . C2 C 0.2870(9) -0.0644(8) 0.2969(6) 0.0250(16) Uani 1 1 d . . . H2A H 0.2033 -0.0541 0.3440 0.030 Uiso 1 1 calc R . . H2B H 0.3660 -0.1290 0.3262 0.030 Uiso 1 1 calc R . . C3 C 0.3120(9) 0.0533(8) 0.2908(7) 0.0271(17) Uani 1 1 d . . . H3A H 0.3197 0.0751 0.3607 0.032 Uiso 1 1 calc R . . H3B H 0.3992 0.0423 0.2479 0.032 Uiso 1 1 calc R . . C4 C 0.1900(9) 0.1536(8) 0.2428(7) 0.0273(17) Uani 1 1 d . . . H4A H 0.2069 0.2281 0.2380 0.033 Uiso 1 1 calc R . . H4B H 0.1048 0.1675 0.2891 0.033 Uiso 1 1 calc R . . C5 C 0.1677(8) 0.1248(7) 0.1341(6) 0.0201(15) Uani 1 1 d . . . C6 C 0.4095(8) -0.1470(8) 0.1176(7) 0.0257(17) Uani 1 1 d . . . H6A H 0.4424 -0.0822 0.1049 0.039 Uiso 1 1 calc R . . H6B H 0.3953 -0.1725 0.0519 0.039 Uiso 1 1 calc R . . H6C H 0.4781 -0.2144 0.1521 0.039 Uiso 1 1 calc R . . C7 C 0.2206(9) -0.2078(7) 0.2064(7) 0.0257(17) Uani 1 1 d . . . H7A H 0.1331 -0.1823 0.2501 0.039 Uiso 1 1 calc R . . H7B H 0.2903 -0.2747 0.2404 0.039 Uiso 1 1 calc R . . H7C H 0.2080 -0.2328 0.1400 0.039 Uiso 1 1 calc R . . C8 C 0.2862(9) 0.1298(8) 0.0525(7) 0.0271(17) Uani 1 1 d . . . H8A H 0.3747 0.0703 0.0714 0.041 Uiso 1 1 calc R . . H8B H 0.2885 0.2094 0.0509 0.041 Uiso 1 1 calc R . . H8C H 0.2694 0.1128 -0.0157 0.041 Uiso 1 1 calc R . . C9 C 0.0267(9) 0.2213(8) 0.1029(7) 0.0262(17) Uani 1 1 d . . . H9A H -0.0481 0.2192 0.1535 0.039 Uiso 1 1 calc R . . H9B H 0.0102 0.2043 0.0346 0.039 Uiso 1 1 calc R . . H9C H 0.0302 0.3004 0.1012 0.039 Uiso 1 1 calc R . . C10 C 0.1727(9) 0.2117(8) -0.3721(6) 0.0248(16) Uani 1 1 d . . . C11 C 0.1506(10) 0.3122(8) -0.4575(7) 0.0323(19) Uani 1 1 d . . . H11A H 0.2202 0.2808 -0.5168 0.039 Uiso 1 1 calc R . . H11B H 0.0584 0.3343 -0.4818 0.039 Uiso 1 1 calc R . . C12 C 0.1617(11) 0.4253(9) -0.4199(8) 0.038(2) Uani 1 1 d . . . H12A H 0.1424 0.4875 -0.4756 0.046 Uiso 1 1 calc R . . H12B H 0.2560 0.4062 -0.4010 0.046 Uiso 1 1 calc R . . C13 C 0.0554(11) 0.4716(8) -0.3248(8) 0.034(2) Uani 1 1 d . . . H13A H -0.0387 0.4964 -0.3464 0.041 Uiso 1 1 calc R . . H13B H 0.0637 0.5427 -0.2994 0.041 Uiso 1 1 calc R . . C14 C 0.0747(10) 0.3760(8) -0.2337(7) 0.0279(18) Uani 1 1 d . . . C15 C 0.3292(9) 0.1512(9) -0.3531(8) 0.035(2) Uani 1 1 d . . . H15A H 0.3589 0.2104 -0.3285 0.052 Uiso 1 1 calc R . . H15B H 0.3839 0.1188 -0.4177 0.052 Uiso 1 1 calc R . . H15C H 0.3426 0.0865 -0.3013 0.052 Uiso 1 1 calc R . . C16 C 0.1265(10) 0.1170(8) -0.4119(7) 0.0313(19) Uani 1 1 d . . . H16A H 0.0289 0.1545 -0.4241 0.047 Uiso 1 1 calc R . . H16B H 0.1399 0.0522 -0.3602 0.047 Uiso 1 1 calc R . . H16C H 0.1818 0.0850 -0.4764 0.047 Uiso 1 1 calc R . . C17 C 0.2049(13) 0.3590(10) -0.1784(9) 0.044(3) Uani 1 1 d . . . H17A H 0.2872 0.3292 -0.2274 0.066 Uiso 1 1 calc R . . H17B H 0.2138 0.3015 -0.1206 0.066 Uiso 1 1 calc R . . H17C H 0.1952 0.4356 -0.1525 0.066 Uiso 1 1 calc R . . C18 C -0.0586(12) 0.4238(9) -0.1553(8) 0.040(2) Uani 1 1 d . . . H18A H -0.1397 0.4341 -0.1903 0.060 Uiso 1 1 calc R . . H18B H -0.0688 0.5006 -0.1295 0.060 Uiso 1 1 calc R . . H18C H -0.0500 0.3665 -0.0974 0.060 Uiso 1 1 calc R . . C19 C 0.4142(8) -0.3356(7) -0.1781(6) 0.0218(15) Uani 1 1 d . . . C20 C 0.4954(10) -0.4643(8) -0.2188(7) 0.0297(18) Uani 1 1 d . . . H20A H 0.5742 -0.5061 -0.1774 0.036 Uiso 1 1 calc R . . H20B H 0.4342 -0.5088 -0.2094 0.036 Uiso 1 1 calc R . . C21 C 0.5503(10) -0.4650(8) -0.3345(7) 0.035(2) Uani 1 1 d . . . H21A H 0.6161 -0.4250 -0.3446 0.042 Uiso 1 1 calc R . . H21B H 0.5987 -0.5481 -0.3575 0.042 Uiso 1 1 calc R . . C22 C 0.4261(10) -0.3986(8) -0.3973(7) 0.033(2) Uani 1 1 d . . . H22A H 0.3645 -0.4427 -0.3895 0.039 Uiso 1 1 calc R . . H22B H 0.4599 -0.3983 -0.4712 0.039 Uiso 1 1 calc R . . C23 C 0.3412(9) -0.2673(8) -0.3646(6) 0.0252(17) Uani 1 1 d . . . C24 C 0.5171(9) -0.2731(9) -0.1675(7) 0.0312(19) Uani 1 1 d . . . H24A H 0.5642 -0.2666 -0.2353 0.047 Uiso 1 1 calc R . . H24B H 0.5854 -0.3206 -0.1203 0.047 Uiso 1 1 calc R . . H24C H 0.4657 -0.1933 -0.1403 0.047 Uiso 1 1 calc R . . C25 C 0.3393(9) -0.3454(8) -0.0692(6) 0.0271(17) Uani 1 1 d . . . H25A H 0.2756 -0.3845 -0.0752 0.041 Uiso 1 1 calc R . . H25B H 0.2876 -0.2653 -0.0424 0.041 Uiso 1 1 calc R . . H25C H 0.4078 -0.3923 -0.0220 0.041 Uiso 1 1 calc R . . C26 C 0.4234(10) -0.1857(8) -0.4014(7) 0.0309(19) Uani 1 1 d . . . H26A H 0.5099 -0.2145 -0.3689 0.046 Uiso 1 1 calc R . . H26B H 0.3676 -0.1034 -0.3817 0.046 Uiso 1 1 calc R . . H26C H 0.4435 -0.1886 -0.4765 0.046 Uiso 1 1 calc R . . C27 C 0.2023(10) -0.2209(9) -0.4160(7) 0.0301(18) Uani 1 1 d . . . H27A H 0.1516 -0.2717 -0.3933 0.045 Uiso 1 1 calc R . . H27B H 0.2219 -0.2232 -0.4911 0.045 Uiso 1 1 calc R . . H27C H 0.1466 -0.1388 -0.3958 0.045 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 0.01227(17) 0.01265(18) 0.01160(17) -0.00106(11) 0.00032(11) -0.00488(12) O1 0.010(2) 0.028(3) 0.005(2) -0.0051(18) 0.0034(16) -0.013(2) O2 0.025(3) 0.016(3) 0.025(3) 0.007(2) -0.004(2) -0.008(2) O3 0.020(3) 0.018(3) 0.023(3) -0.006(2) 0.003(2) -0.005(2) N1 0.014(3) 0.015(3) 0.012(3) -0.002(2) -0.001(2) -0.007(2) N2 0.024(3) 0.016(3) 0.019(3) 0.002(2) -0.003(2) -0.009(3) N3 0.021(3) 0.016(3) 0.018(3) -0.005(2) 0.000(2) -0.005(2) C1 0.016(3) 0.024(4) 0.019(4) 0.002(3) -0.002(3) -0.004(3) C2 0.023(4) 0.030(4) 0.020(4) 0.001(3) -0.005(3) -0.007(3) C3 0.024(4) 0.037(5) 0.024(4) -0.003(3) -0.008(3) -0.015(4) C4 0.028(4) 0.031(4) 0.026(4) -0.010(3) 0.002(3) -0.014(4) C5 0.020(4) 0.018(4) 0.024(4) 0.001(3) -0.003(3) -0.010(3) C6 0.015(4) 0.028(4) 0.030(4) -0.004(3) 0.001(3) -0.004(3) C7 0.023(4) 0.021(4) 0.029(4) 0.002(3) -0.004(3) -0.004(3) C8 0.031(4) 0.029(4) 0.028(4) 0.003(3) -0.002(3) -0.020(4) C9 0.028(4) 0.021(4) 0.035(4) 0.003(3) -0.008(3) -0.013(3) C10 0.025(4) 0.021(4) 0.024(4) 0.002(3) 0.001(3) -0.005(3) C11 0.033(5) 0.029(5) 0.032(5) 0.006(4) 0.000(4) -0.011(4) C12 0.036(5) 0.029(5) 0.047(6) 0.016(4) -0.003(4) -0.013(4) C13 0.049(6) 0.016(4) 0.037(5) 0.006(3) -0.011(4) -0.013(4) C14 0.038(5) 0.020(4) 0.030(4) 0.002(3) -0.006(4) -0.015(4) C15 0.023(4) 0.028(5) 0.049(6) 0.008(4) -0.005(4) -0.007(4) C16 0.035(5) 0.019(4) 0.034(5) -0.004(3) -0.002(4) -0.004(4) C17 0.061(7) 0.035(5) 0.050(6) 0.012(5) -0.026(5) -0.030(5) C18 0.058(7) 0.022(5) 0.038(5) -0.007(4) -0.001(5) -0.014(4) C19 0.019(4) 0.020(4) 0.023(4) -0.001(3) -0.004(3) -0.004(3) C20 0.034(5) 0.018(4) 0.029(4) -0.002(3) -0.005(4) -0.001(3) C21 0.038(5) 0.022(4) 0.030(5) -0.008(3) -0.004(4) 0.004(4) C22 0.043(5) 0.020(4) 0.027(4) -0.007(3) -0.007(4) -0.001(4) C23 0.028(4) 0.022(4) 0.018(4) -0.005(3) 0.000(3) -0.002(3) C24 0.028(4) 0.036(5) 0.033(5) -0.005(4) -0.005(4) -0.015(4) C25 0.031(4) 0.026(4) 0.018(4) 0.002(3) -0.005(3) -0.004(3) C26 0.029(4) 0.030(5) 0.028(4) 0.003(3) 0.004(3) -0.008(4) C27 0.032(5) 0.031(5) 0.028(4) -0.003(3) -0.004(3) -0.013(4) _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 O3 2.110(5) . ? Sm1 O2 2.124(5) . ? Sm1 O1 2.295(4) . ? Sm1 O1 2.354(4) 2 ? Sm1 N1 2.537(6) 2 ? Sm1 Sm1 3.7027(8) 2 ? O1 N1 1.434(7) . ? O1 Sm1 2.354(4) 2 ? O2 N2 1.433(8) . ? O3 N3 1.427(8) . ? N1 C1 1.504(9) . ? N1 C5 1.514(9) . ? N1 Sm1 2.537(6) 2 ? N2 C14 1.486(10) . ? N2 C10 1.489(10) . ? N3 C23 1.496(10) . ? N3 C19 1.497(10) . ? C1 C7 1.530(11) . ? C1 C2 1.542(11) . ? C1 C6 1.547(11) . ? C2 C3 1.523(12) . ? C3 C4 1.516(12) . ? C4 C5 1.521(11) . ? C5 C8 1.538(11) . ? C5 C9 1.540(11) . ? C10 C16 1.528(12) . ? C10 C11 1.532(12) . ? C10 C15 1.538(12) . ? C11 C12 1.518(14) . ? C12 C13 1.523(14) . ? C13 C14 1.546(12) . ? C14 C17 1.534(13) . ? C14 C18 1.546(14) . ? C19 C20 1.531(11) . ? C19 C25 1.537(11) . ? C19 C24 1.548(12) . ? C20 C21 1.524(13) . ? C21 C22 1.510(13) . ? C22 C23 1.529(11) . ? C23 C27 1.535(12) . ? C23 C26 1.549(13) . ? 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 O3 Sm1 O2 111.5(2) . . ? O3 Sm1 O1 107.2(2) . . ? O2 Sm1 O1 111.1(2) . . ? O3 Sm1 O1 126.68(19) . 2 ? O2 Sm1 O1 117.3(2) . 2 ? O1 Sm1 O1 74.41(18) . 2 ? O3 Sm1 N1 105.6(2) . 2 ? O2 Sm1 N1 114.8(2) . 2 ? O1 Sm1 N1 106.21(17) . 2 ? O1 Sm1 N1 33.84(16) 2 2 ? O3 Sm1 Sm1 124.24(15) . 2 ? O2 Sm1 Sm1 120.98(16) . 2 ? O1 Sm1 Sm1 37.76(11) . 2 ? O1 Sm1 Sm1 36.65(11) 2 2 ? N1 Sm1 Sm1 69.21(13) 2 2 ? N1 O1 Sm1 159.3(4) . . ? N1 O1 Sm1 80.1(3) . 2 ? Sm1 O1 Sm1 105.59(18) . 2 ? N2 O2 Sm1 150.3(5) . . ? N3 O3 Sm1 159.9(5) . . ? O1 N1 C1 112.0(5) . . ? O1 N1 C5 108.1(5) . . ? C1 N1 C5 116.6(6) . . ? O1 N1 Sm1 66.1(3) . 2 ? C1 N1 Sm1 119.8(4) . 2 ? C5 N1 Sm1 120.6(4) . 2 ? O2 N2 C14 109.2(6) . . ? O2 N2 C10 107.5(6) . . ? C14 N2 C10 118.6(6) . . ? O3 N3 C23 109.1(6) . . ? O3 N3 C19 108.1(6) . . ? C23 N3 C19 118.2(6) . . ? N1 C1 C7 107.7(6) . . ? N1 C1 C2 107.9(6) . . ? C7 C1 C2 107.7(7) . . ? N1 C1 C6 114.2(6) . . ? C7 C1 C6 107.6(7) . . ? C2 C1 C6 111.6(7) . . ? C3 C2 C1 112.4(7) . . ? C4 C3 C2 109.0(7) . . ? C3 C4 C5 113.3(7) . . ? N1 C5 C4 108.1(6) . . ? N1 C5 C8 113.9(6) . . ? C4 C5 C8 110.7(7) . . ? N1 C5 C9 107.0(6) . . ? C4 C5 C9 108.2(7) . . ? C8 C5 C9 108.7(7) . . ? N2 C10 C16 106.1(7) . . ? N2 C10 C11 108.4(7) . . ? C16 C10 C11 107.4(7) . . ? N2 C10 C15 115.4(7) . . ? C16 C10 C15 109.1(7) . . ? C11 C10 C15 110.0(7) . . ? C12 C11 C10 113.2(8) . . ? C11 C12 C13 108.6(8) . . ? C12 C13 C14 113.4(8) . . ? N2 C14 C17 115.7(8) . . ? N2 C14 C18 105.9(7) . . ? C17 C14 C18 109.9(8) . . ? N2 C14 C13 107.3(7) . . ? C17 C14 C13 110.4(8) . . ? C18 C14 C13 107.3(8) . . ? N3 C19 C20 108.4(6) . . ? N3 C19 C25 106.4(6) . . ? C20 C19 C25 108.3(7) . . ? N3 C19 C24 114.4(7) . . ? C20 C19 C24 110.0(7) . . ? C25 C19 C24 109.1(7) . . ? C21 C20 C19 112.8(7) . . ? C22 C21 C20 108.1(8) . . ? C21 C22 C23 113.7(7) . . ? N3 C23 C22 108.1(7) . . ? N3 C23 C27 105.6(7) . . ? C22 C23 C27 108.0(7) . . ? N3 C23 C26 114.6(7) . . ? C22 C23 C26 110.6(7) . . ? C27 C23 C26 109.6(7) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 5.720 _refine_diff_density_min -4.412 _refine_diff_density_rms 0.238 data_jp3 _database_code_CSD 170800 _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H66 Cl2 N2 O2 Sm2' _chemical_formula_weight 954.53 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Sm' 'Sm' -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.5950(19) _cell_length_b 8.3464(11) _cell_length_c 17.584(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.306(2) _cell_angle_gamma 90.00 _cell_volume 2055.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 163(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 964 _exptl_absorpt_coefficient_mu 2.990 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5463 _exptl_absorpt_correction_T_max 0.8180 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 163(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 1.0' _diffrn_reflns_number 20947 _diffrn_reflns_av_R_equivalents 0.0741 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5015 _reflns_number_gt 3567 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART/SAINT' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+3.7826P] 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 5015 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 -0.109786(17) 0.39792(3) -0.450123(14) 0.01972(8) Uani 1 1 d . . . Cl1 Cl 0.05320(8) 0.31157(15) -0.49454(7) 0.0270(3) Uani 1 1 d . . . O1 O -0.1535(2) 0.3232(4) -0.34815(19) 0.0277(8) Uani 1 1 d . . . N1 N -0.0719(3) 0.4092(5) -0.3012(2) 0.0227(8) Uani 1 1 d . . . C1 C -0.1973(3) 0.2051(6) -0.5710(3) 0.0246(11) Uani 1 1 d . . . C2 C -0.2444(3) 0.1808(6) -0.5118(3) 0.0246(11) Uani 1 1 d . . . C3 C -0.2946(3) 0.3211(6) -0.5060(3) 0.0264(11) Uani 1 1 d . . . C4 C -0.2783(4) 0.4351(6) -0.5598(3) 0.0279(12) Uani 1 1 d . . . C5 C -0.2168(4) 0.3609(6) -0.6006(3) 0.0250(11) Uani 1 1 d . . . C6 C -0.1427(4) 0.0812(7) -0.6029(3) 0.0401(14) Uani 1 1 d . . . H6A H -0.1390 -0.0183 -0.5726 0.060 Uiso 1 1 calc R . . H6B H -0.0780 0.1207 -0.5980 0.060 Uiso 1 1 calc R . . H6C H -0.1754 0.0606 -0.6588 0.060 Uiso 1 1 calc R . . C7 C -0.2436(4) 0.0289(6) -0.4660(3) 0.0353(13) Uani 1 1 d . . . H7A H -0.2025 -0.0502 -0.4814 0.053 Uiso 1 1 calc R . . H7B H -0.3087 -0.0134 -0.4774 0.053 Uiso 1 1 calc R . . H7C H -0.2190 0.0511 -0.4092 0.053 Uiso 1 1 calc R . . C8 C -0.3623(4) 0.3388(8) -0.4549(3) 0.0387(14) Uani 1 1 d . . . H8A H -0.3889 0.4474 -0.4607 0.058 Uiso 1 1 calc R . . H8B H -0.3275 0.3199 -0.3993 0.058 Uiso 1 1 calc R . . H8C H -0.4142 0.2607 -0.4716 0.058 Uiso 1 1 calc R . . C9 C -0.3218(4) 0.5995(7) -0.5764(4) 0.0417(14) Uani 1 1 d . . . H9A H -0.2974 0.6526 -0.6165 0.063 Uiso 1 1 calc R . . H9B H -0.3048 0.6629 -0.5275 0.063 Uiso 1 1 calc R . . H9C H -0.3914 0.5900 -0.5960 0.063 Uiso 1 1 calc R . . C10 C -0.1864(4) 0.4327(7) -0.6684(3) 0.0407(15) Uani 1 1 d . . . H10A H -0.2086 0.5439 -0.6766 0.061 Uiso 1 1 calc R . . H10B H -0.2142 0.3707 -0.7167 0.061 Uiso 1 1 calc R . . H10C H -0.1166 0.4303 -0.6560 0.061 Uiso 1 1 calc R . . C11 C -0.1074(4) 0.5556(6) -0.2670(3) 0.0285(12) Uani 1 1 d . . . C12 C -0.0195(4) 0.6385(6) -0.2119(3) 0.0374(14) Uani 1 1 d . . . H12A H 0.0203 0.6822 -0.2443 0.045 Uiso 1 1 calc R . . H12B H -0.0410 0.7296 -0.1852 0.045 Uiso 1 1 calc R . . C13 C 0.0409(4) 0.5270(7) -0.1496(3) 0.0416(15) Uani 1 1 d . . . H13A H 0.0968 0.5856 -0.1164 0.050 Uiso 1 1 calc R . . H13B H 0.0029 0.4872 -0.1149 0.050 Uiso 1 1 calc R . . C14 C 0.0737(4) 0.3882(7) -0.1900(3) 0.0351(13) Uani 1 1 d . . . H14A H 0.1121 0.3147 -0.1491 0.042 Uiso 1 1 calc R . . H14B H 0.1155 0.4290 -0.2213 0.042 Uiso 1 1 calc R . . C15 C -0.0086(4) 0.2946(6) -0.2446(3) 0.0265(11) Uani 1 1 d . . . C16 C -0.1526(4) 0.6660(7) -0.3365(3) 0.0387(14) Uani 1 1 d . . . H16A H -0.1053 0.6928 -0.3645 0.058 Uiso 1 1 calc R . . H16B H -0.1746 0.7644 -0.3168 0.058 Uiso 1 1 calc R . . H16C H -0.2070 0.6117 -0.3729 0.058 Uiso 1 1 calc R . . C17 C -0.1818(4) 0.5161(7) -0.2239(3) 0.0408(14) Uani 1 1 d . . . H17A H -0.2367 0.4637 -0.2607 0.061 Uiso 1 1 calc R . . H17B H -0.2028 0.6151 -0.2039 0.061 Uiso 1 1 calc R . . H17C H -0.1538 0.4440 -0.1794 0.061 Uiso 1 1 calc R . . C18 C -0.0593(4) 0.1921(7) -0.1957(3) 0.0320(12) Uani 1 1 d . . . H18A H -0.1121 0.1333 -0.2316 0.048 Uiso 1 1 calc R . . H18B H -0.0843 0.2620 -0.1614 0.048 Uiso 1 1 calc R . . H18C H -0.0138 0.1160 -0.1631 0.048 Uiso 1 1 calc R . . C19 C 0.0323(4) 0.1784(7) -0.2948(3) 0.0374(13) Uani 1 1 d . . . H19A H -0.0199 0.1168 -0.3299 0.056 Uiso 1 1 calc R . . H19B H 0.0773 0.1049 -0.2598 0.056 Uiso 1 1 calc R . . H19C H 0.0655 0.2394 -0.3267 0.056 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 0.01839(12) 0.02205(12) 0.01782(12) -0.00096(12) 0.00359(8) 0.00045(12) Cl1 0.0257(6) 0.0234(6) 0.0343(7) 0.0026(5) 0.0123(5) 0.0040(5) O1 0.0218(18) 0.039(2) 0.0203(17) -0.0058(16) 0.0027(14) -0.0085(16) N1 0.019(2) 0.026(2) 0.021(2) -0.0037(18) 0.0033(16) 0.0008(18) C1 0.025(3) 0.026(3) 0.019(2) -0.005(2) 0.000(2) -0.004(2) C2 0.025(3) 0.028(3) 0.018(2) 0.000(2) 0.001(2) -0.005(2) C3 0.023(3) 0.034(3) 0.021(3) -0.004(2) 0.004(2) -0.005(2) C4 0.023(3) 0.024(3) 0.028(3) -0.003(2) -0.008(2) 0.000(2) C5 0.024(3) 0.029(3) 0.020(2) 0.001(2) 0.002(2) -0.007(2) C6 0.043(3) 0.039(3) 0.038(3) -0.013(3) 0.011(3) 0.002(3) C7 0.044(3) 0.028(3) 0.030(3) 0.005(2) 0.004(3) -0.010(3) C8 0.029(3) 0.056(4) 0.033(3) -0.009(3) 0.011(2) -0.004(3) C9 0.036(3) 0.031(3) 0.052(4) 0.000(3) 0.002(3) 0.005(3) C10 0.046(4) 0.047(4) 0.028(3) 0.007(3) 0.009(3) -0.006(3) C11 0.036(3) 0.027(3) 0.024(3) -0.003(2) 0.011(2) 0.007(2) C12 0.050(4) 0.035(3) 0.026(3) -0.010(2) 0.010(3) -0.005(3) C13 0.046(4) 0.048(4) 0.023(3) -0.005(3) -0.002(3) -0.015(3) C14 0.022(3) 0.049(3) 0.031(3) 0.014(3) 0.001(2) 0.002(3) C15 0.025(3) 0.031(3) 0.024(3) 0.002(2) 0.007(2) 0.002(2) C16 0.052(4) 0.037(3) 0.029(3) 0.001(3) 0.014(3) 0.019(3) C17 0.042(4) 0.049(4) 0.036(3) 0.000(3) 0.019(3) 0.014(3) C18 0.030(3) 0.034(3) 0.032(3) 0.011(2) 0.008(2) 0.003(2) C19 0.040(3) 0.034(3) 0.042(3) 0.008(3) 0.017(3) 0.016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Sm1 Cnt 2.396 . ? Sm1 O1 2.157(3) . ? Sm1 N1 2.522(4) . ? Sm1 C2 2.669(5) . ? Sm1 C3 2.677(5) . ? Sm1 C4 2.684(5) . ? Sm1 C5 2.686(5) . ? Sm1 C1 2.686(5) . ? Sm1 Cl1 2.7985(12) . ? Sm1 Cl1 2.8212(13) 3_564 ? Cl1 Sm1 2.8212(13) 3_564 ? O1 N1 1.436(5) . ? N1 C15 1.498(6) . ? N1 C11 1.516(6) . ? C1 C5 1.399(7) . ? C1 C2 1.413(7) . ? C1 C6 1.508(7) . ? C2 C3 1.401(7) . ? C2 C7 1.500(7) . ? C3 C4 1.409(7) . ? C3 C8 1.517(7) . ? C4 C5 1.436(7) . ? C4 C9 1.505(7) . ? C5 C10 1.509(7) . ? C11 C17 1.524(7) . ? C11 C16 1.525(7) . ? C11 C12 1.537(7) . ? C12 C13 1.517(8) . ? C13 C14 1.506(8) . ? C14 C15 1.525(7) . ? C15 C19 1.540(7) . ? C15 C18 1.542(7) . ? 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 Cnt Sm1 Cl1 107.8 . . ? Cnt Sm1 Cl1 107.6 3_564 . ? Cnt Sm1 O1 97.5 . . ? Cnt Sm1 N1 131.9 . . ? O1 Sm1 N1 34.65(12) . . ? O1 Sm1 C2 77.64(13) . . ? N1 Sm1 C2 111.67(14) . . ? O1 Sm1 C3 74.53(13) . . ? N1 Sm1 C3 107.13(13) . . ? C2 Sm1 C3 30.37(15) . . ? O1 Sm1 C4 101.89(15) . . ? N1 Sm1 C4 129.17(15) . . ? C2 Sm1 C4 50.58(15) . . ? C3 Sm1 C4 30.48(15) . . ? O1 Sm1 C5 124.04(13) . . ? N1 Sm1 C5 157.60(14) . . ? C2 Sm1 C5 50.47(14) . . ? C3 Sm1 C5 50.48(15) . . ? C4 Sm1 C5 31.03(15) . . ? O1 Sm1 C1 107.39(14) . . ? N1 Sm1 C1 139.56(14) . . ? C2 Sm1 C1 30.60(14) . . ? C3 Sm1 C1 50.18(15) . . ? C4 Sm1 C1 50.51(15) . . ? C5 Sm1 C1 30.20(14) . . ? O1 Sm1 Cl1 129.08(10) . . ? N1 Sm1 Cl1 110.10(9) . . ? C2 Sm1 Cl1 107.34(11) . . ? C3 Sm1 Cl1 133.15(11) . . ? C4 Sm1 Cl1 120.56(12) . . ? C5 Sm1 Cl1 90.02(11) . . ? C1 Sm1 Cl1 82.98(11) . . ? O1 Sm1 Cl1 135.94(10) . 3_564 ? N1 Sm1 Cl1 109.02(10) . 3_564 ? C2 Sm1 Cl1 134.17(11) . 3_564 ? C3 Sm1 Cl1 116.22(12) . 3_564 ? C4 Sm1 Cl1 87.17(11) . 3_564 ? C5 Sm1 Cl1 84.53(10) . 3_564 ? C1 Sm1 Cl1 111.24(11) . 3_564 ? Cl1 Sm1 Cl1 76.76(4) . 3_564 ? Sm1 Cl1 Sm1 103.24(4) . 3_564 ? N1 O1 Sm1 86.7(2) . . ? O1 N1 C15 108.7(4) . . ? O1 N1 C11 108.1(3) . . ? C15 N1 C11 117.9(4) . . ? O1 N1 Sm1 58.62(18) . . ? C15 N1 Sm1 125.5(3) . . ? C11 N1 Sm1 116.3(3) . . ? C5 C1 C2 108.5(5) . . ? C5 C1 C6 124.9(5) . . ? C2 C1 C6 126.3(5) . . ? C5 C1 Sm1 74.9(3) . . ? C2 C1 Sm1 74.0(3) . . ? C6 C1 Sm1 121.4(3) . . ? C3 C2 C1 107.8(4) . . ? C3 C2 C7 126.3(5) . . ? C1 C2 C7 125.8(5) . . ? C3 C2 Sm1 75.1(3) . . ? C1 C2 Sm1 75.4(3) . . ? C7 C2 Sm1 117.5(3) . . ? C2 C3 C4 108.9(4) . . ? C2 C3 C8 124.5(5) . . ? C4 C3 C8 126.4(5) . . ? C2 C3 Sm1 74.5(3) . . ? C4 C3 Sm1 75.0(3) . . ? C8 C3 Sm1 121.0(3) . . ? C3 C4 C5 106.9(4) . . ? C3 C4 C9 127.2(5) . . ? C5 C4 C9 125.8(5) . . ? C3 C4 Sm1 74.5(3) . . ? C5 C4 Sm1 74.5(3) . . ? C9 C4 Sm1 119.7(3) . . ? C1 C5 C4 107.8(4) . . ? C1 C5 C10 126.1(5) . . ? C4 C5 C10 125.9(5) . . ? C1 C5 Sm1 74.9(3) . . ? C4 C5 Sm1 74.4(3) . . ? C10 C5 Sm1 120.9(3) . . ? N1 C11 C17 113.2(4) . . ? N1 C11 C16 106.7(4) . . ? C17 C11 C16 108.7(4) . . ? N1 C11 C12 107.1(4) . . ? C17 C11 C12 111.7(4) . . ? C16 C11 C12 109.2(5) . . ? C13 C12 C11 113.1(4) . . ? C14 C13 C12 109.2(4) . . ? C13 C14 C15 113.1(4) . . ? N1 C15 C14 108.7(4) . . ? N1 C15 C19 106.7(4) . . ? C14 C15 C19 108.7(4) . . ? N1 C15 C18 114.9(4) . . ? C14 C15 C18 110.5(4) . . ? C19 C15 C18 107.1(4) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.014 _refine_diff_density_min -0.807 _refine_diff_density_rms 0.161