# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Gael Zucchi' 'Dmitry Aldakov' 'Michel Ephritikhine' 'Bernard Geffroy' 'Taewoo Jeon' 'Pierre Thuery' 'Denis Tondelier' _publ_contact_author_name 'Gael Zucchi' _publ_contact_author_email GAEL.ZUCCHI@CEA.FR _publ_section_title ; White Electroluminescence of Lanthanide Complexes Resulting from Exciplex Formation ; # Attachment 'CIF.txt' data_1 _database_code_depnum_ccdc_archive 'CCDC 752071' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H48 Eu2 N4 O12' _chemical_formula_weight 1056.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2290(4) _cell_length_b 9.8631(5) _cell_length_c 12.4794(6) _cell_angle_alpha 107.066(2) _cell_angle_beta 97.152(3) _cell_angle_gamma 96.245(3) _cell_volume 1064.77(9) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 51854 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 526 _exptl_absorpt_coefficient_mu 2.980 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.490 _exptl_absorpt_correction_T_max 0.812 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 area-detector diffractometer' _diffrn_measurement_method 'two \f and thirteen \w scans with 2\% steps' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 51854 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4032 _reflns_number_gt 3879 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by Patterson map interpretation and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (CH) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0148P)^2^+0.3919P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _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 4032 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0174 _refine_ls_R_factor_gt 0.0155 _refine_ls_wR_factor_ref 0.0367 _refine_ls_wR_factor_gt 0.0363 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.359 _refine_diff_density_min -0.763 _refine_diff_density_rms 0.071 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 Eu Eu 0.704437(9) 0.746892(9) 0.839593(8) 0.01556(4) Uani 1 1 d . . . O1 O 0.82095(15) 0.66660(15) 0.98042(13) 0.0260(3) Uani 1 1 d . . . O2 O 0.54224(15) 0.74772(14) 0.96903(12) 0.0232(3) Uani 1 1 d . . . O3 O 0.78742(16) 0.54588(14) 0.72804(13) 0.0264(3) Uani 1 1 d . . . O4 O 0.49578(15) 0.59035(15) 0.72722(13) 0.0272(3) Uani 1 1 d . . . O5 O 0.79490(15) 0.82803(15) 0.69870(13) 0.0268(3) Uani 1 1 d . . . O6 O 0.54530(15) 0.89928(14) 0.79078(12) 0.0238(3) Uani 1 1 d . . . N1 N 0.98902(17) 0.83717(17) 0.88520(14) 0.0200(3) Uani 1 1 d . . . N2 N 1.19610(17) 1.00680(17) 0.99930(14) 0.0205(4) Uani 1 1 d . . . C1 C 1.0507(2) 0.9567(2) 0.96815(17) 0.0182(4) Uani 1 1 d . . . C2 C 1.2852(2) 0.9267(2) 0.94029(19) 0.0260(5) Uani 1 1 d . . . H2 H 1.3867 0.9572 0.9589 0.031 Uiso 1 1 calc R . . C3 C 1.2326(2) 0.8002(2) 0.85257(19) 0.0261(5) Uani 1 1 d . . . H3 H 1.2962 0.7458 0.8127 0.031 Uiso 1 1 calc R . . C4 C 1.0816(2) 0.7591(2) 0.82732(18) 0.0228(4) Uani 1 1 d . . . H4 H 1.0425 0.6751 0.7687 0.027 Uiso 1 1 calc R . . C5 C 0.9095(3) 0.5936(3) 1.1370(2) 0.0384(6) Uani 1 1 d . . . H5A H 0.9427 0.5114 1.0893 0.058 Uiso 1 1 calc R . . H5B H 0.8726 0.5699 1.1989 0.058 Uiso 1 1 calc R . . H5C H 0.9905 0.6712 1.1664 0.058 Uiso 1 1 calc R . . C6 C 0.7878(2) 0.6383(2) 1.06827(19) 0.0260(5) Uani 1 1 d . . . C7 C 0.6499(2) 0.6449(2) 1.10270(19) 0.0286(5) Uani 1 1 d . . . H7 H 0.6340 0.6133 1.1641 0.034 Uiso 1 1 calc R . . C8 C 0.5338(2) 0.6961(2) 1.05067(18) 0.0249(4) Uani 1 1 d . . . C9 C 0.3894(2) 0.6971(2) 1.0960(2) 0.0315(5) Uani 1 1 d . . . H9A H 0.3741 0.7944 1.1286 0.047 Uiso 1 1 calc R . . H9B H 0.3926 0.6497 1.1531 0.047 Uiso 1 1 calc R . . H9C H 0.3097 0.6478 1.0350 0.047 Uiso 1 1 calc R . . C10 C 0.8383(3) 0.3488(3) 0.5847(2) 0.0432(6) Uani 1 1 d . . . H10A H 0.9170 0.4100 0.5706 0.065 Uiso 1 1 calc R . . H10B H 0.7878 0.2818 0.5139 0.065 Uiso 1 1 calc R . . H10C H 0.8784 0.2974 0.6330 0.065 Uiso 1 1 calc R . . C11 C 0.7306(2) 0.4390(2) 0.64241(19) 0.0265(5) Uani 1 1 d . . . C12 C 0.5803(2) 0.3994(2) 0.59919(19) 0.0285(5) Uani 1 1 d . . . H12 H 0.5509 0.3174 0.5367 0.034 Uiso 1 1 calc R . . C13 C 0.4710(2) 0.4757(2) 0.64417(18) 0.0253(5) Uani 1 1 d . . . C14 C 0.3109(2) 0.4181(3) 0.5927(2) 0.0346(5) Uani 1 1 d . . . H14A H 0.2754 0.3448 0.6235 0.052 Uiso 1 1 calc R . . H14B H 0.3026 0.3783 0.5117 0.052 Uiso 1 1 calc R . . H14C H 0.2532 0.4947 0.6101 0.052 Uiso 1 1 calc R . . C15 C 0.8786(3) 0.9509(3) 0.5773(2) 0.0350(5) Uani 1 1 d . . . H15A H 0.9625 1.0121 0.6286 0.053 Uiso 1 1 calc R . . H15B H 0.8376 0.9998 0.5274 0.053 Uiso 1 1 calc R . . H15C H 0.9091 0.8645 0.5333 0.053 Uiso 1 1 calc R . . C16 C 0.7634(2) 0.9135(2) 0.64424(18) 0.0252(4) Uani 1 1 d . . . C17 C 0.6325(2) 0.9721(2) 0.64272(19) 0.0287(5) Uani 1 1 d . . . H17 H 0.6137 1.0245 0.5930 0.034 Uiso 1 1 calc R . . C18 C 0.5283(2) 0.9561(2) 0.71198(18) 0.0248(4) Uani 1 1 d . . . C19 C 0.3831(2) 1.0113(2) 0.6933(2) 0.0328(5) Uani 1 1 d . . . H19A H 0.3052 0.9316 0.6589 0.049 Uiso 1 1 calc R . . H19B H 0.3902 1.0698 0.6442 0.049 Uiso 1 1 calc R . . H19C H 0.3619 1.0675 0.7650 0.049 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 Eu 0.01210(6) 0.01683(6) 0.01710(6) 0.00485(4) 0.00222(4) 0.00084(4) O1 0.0234(8) 0.0319(8) 0.0267(9) 0.0147(7) 0.0049(7) 0.0052(6) O2 0.0193(7) 0.0270(7) 0.0251(8) 0.0097(6) 0.0068(6) 0.0026(6) O3 0.0246(8) 0.0214(7) 0.0281(9) 0.0013(6) 0.0012(7) 0.0037(6) O4 0.0205(7) 0.0291(8) 0.0260(8) 0.0020(7) 0.0025(6) -0.0021(6) O5 0.0254(8) 0.0356(8) 0.0263(8) 0.0168(7) 0.0089(7) 0.0084(6) O6 0.0195(7) 0.0273(7) 0.0259(8) 0.0096(6) 0.0036(6) 0.0063(6) N1 0.0171(8) 0.0207(8) 0.0217(9) 0.0062(7) 0.0034(7) 0.0017(6) N2 0.0155(8) 0.0216(8) 0.0230(10) 0.0055(7) 0.0021(7) 0.0021(6) C1 0.0162(9) 0.0196(9) 0.0209(11) 0.0095(8) 0.0033(8) 0.0027(7) C2 0.0149(10) 0.0292(11) 0.0309(13) 0.0048(9) 0.0049(9) 0.0025(8) C3 0.0199(10) 0.0268(10) 0.0293(12) 0.0036(9) 0.0060(9) 0.0061(8) C4 0.0201(10) 0.0214(10) 0.0247(11) 0.0040(8) 0.0042(9) 0.0029(8) C5 0.0402(14) 0.0480(14) 0.0331(14) 0.0195(12) 0.0050(11) 0.0138(11) C6 0.0316(12) 0.0214(10) 0.0245(12) 0.0071(9) 0.0034(10) 0.0037(8) C7 0.0366(12) 0.0283(11) 0.0233(12) 0.0103(9) 0.0089(10) 0.0049(9) C8 0.0279(11) 0.0188(9) 0.0246(12) 0.0017(8) 0.0087(9) -0.0024(8) C9 0.0315(12) 0.0326(12) 0.0314(13) 0.0089(10) 0.0133(10) 0.0023(9) C10 0.0409(14) 0.0395(13) 0.0366(15) -0.0057(11) -0.0048(12) 0.0151(11) C11 0.0317(12) 0.0221(10) 0.0239(12) 0.0061(9) 0.0005(10) 0.0048(9) C12 0.0321(12) 0.0228(10) 0.0240(12) 0.0018(9) -0.0018(10) -0.0012(9) C13 0.0264(11) 0.0271(11) 0.0210(11) 0.0095(9) 0.0009(9) -0.0035(8) C14 0.0278(12) 0.0436(13) 0.0252(13) 0.0053(10) 0.0014(10) -0.0073(10) C15 0.0345(13) 0.0395(13) 0.0358(14) 0.0183(11) 0.0100(11) 0.0026(10) C16 0.0278(11) 0.0258(10) 0.0201(11) 0.0059(9) 0.0036(9) 0.0000(8) C17 0.0335(12) 0.0293(11) 0.0267(12) 0.0135(9) 0.0041(10) 0.0070(9) C18 0.0252(11) 0.0210(10) 0.0237(11) 0.0027(8) -0.0026(9) 0.0042(8) C19 0.0303(12) 0.0360(12) 0.0332(13) 0.0116(10) 0.0011(10) 0.0123(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Eu O1 2.3246(14) . ? Eu O3 2.3304(13) . ? Eu O2 2.3339(13) . ? Eu O4 2.3385(14) . ? Eu O5 2.3399(13) . ? Eu O6 2.3626(13) . ? Eu N1 2.6146(16) . ? Eu N2 2.6410(17) 2_777 ? O1 C6 1.272(2) . ? O2 C8 1.272(2) . ? O3 C11 1.268(3) . ? O4 C13 1.266(3) . ? O5 C16 1.264(2) . ? O6 C18 1.269(2) . ? N1 C1 1.333(3) . ? N1 C4 1.348(2) . ? N2 C2 1.339(3) . ? N2 C1 1.345(3) . ? N2 Eu 2.6410(16) 2_777 ? C1 C1 1.483(4) 2_777 ? C2 C3 1.387(3) . ? C2 H2 0.9300 . ? C3 C4 1.378(3) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 C6 1.510(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.395(3) . ? C7 C8 1.400(3) . ? C7 H7 0.9300 . ? C8 C9 1.511(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.514(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.393(3) . ? C12 C13 1.399(3) . ? C12 H12 0.9300 . ? C13 C14 1.511(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.511(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.394(3) . ? C17 C18 1.397(3) . ? C17 H17 0.9300 . ? C18 C19 1.518(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Eu O3 79.76(5) . . ? O1 Eu O2 73.12(5) . . ? O3 Eu O2 126.10(5) . . ? O1 Eu O4 114.08(5) . . ? O3 Eu O4 72.87(5) . . ? O2 Eu O4 77.12(5) . . ? O1 Eu O5 131.67(5) . . ? O3 Eu O5 76.96(5) . . ? O2 Eu O5 152.06(5) . . ? O4 Eu O5 98.54(5) . . ? O1 Eu O6 147.98(5) . . ? O3 Eu O6 131.32(5) . . ? O2 Eu O6 80.15(5) . . ? O4 Eu O6 75.64(5) . . ? O5 Eu O6 72.09(5) . . ? O1 Eu N1 68.14(5) . . ? O3 Eu N1 80.16(5) . . ? O2 Eu N1 127.42(5) . . ? O4 Eu N1 151.70(5) . . ? O5 Eu N1 66.53(5) . . ? O6 Eu N1 118.44(5) . . ? O1 Eu N2 79.34(5) . 2_777 ? O3 Eu N2 141.06(5) . 2_777 ? O2 Eu N2 77.62(5) . 2_777 ? O4 Eu N2 146.03(5) . 2_777 ? O5 Eu N2 93.26(5) . 2_777 ? O6 Eu N2 77.96(5) . 2_777 ? N1 Eu N2 61.62(5) . 2_777 ? C6 O1 Eu 136.47(13) . . ? C8 O2 Eu 135.53(13) . . ? C11 O3 Eu 135.57(14) . . ? C13 O4 Eu 136.33(13) . . ? C16 O5 Eu 137.40(13) . . ? C18 O6 Eu 135.24(13) . . ? C1 N1 C4 116.66(17) . . ? C1 N1 Eu 122.97(12) . . ? C4 N1 Eu 120.31(13) . . ? C2 N2 C1 115.59(18) . . ? C2 N2 Eu 122.75(13) . 2_777 ? C1 N2 Eu 121.61(12) . 2_777 ? N1 C1 N2 126.32(17) . . ? N1 C1 C1 116.9(2) . 2_777 ? N2 C1 C1 116.8(2) . 2_777 ? N2 C2 C3 122.77(19) . . ? N2 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C4 C3 C2 116.85(18) . . ? C4 C3 H3 121.6 . . ? C2 C3 H3 121.6 . . ? N1 C4 C3 121.81(19) . . ? N1 C4 H4 119.1 . . ? C3 C4 H4 119.1 . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C6 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O1 C6 C7 124.7(2) . . ? O1 C6 C5 115.60(18) . . ? C7 C6 C5 119.69(19) . . ? C6 C7 C8 124.17(19) . . ? C6 C7 H7 117.9 . . ? C8 C7 H7 117.9 . . ? O2 C8 C7 124.51(18) . . ? O2 C8 C9 116.46(19) . . ? C7 C8 C9 118.98(19) . . ? 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 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 C12 125.5(2) . . ? O3 C11 C10 115.7(2) . . ? C12 C11 C10 118.8(2) . . ? C11 C12 C13 123.9(2) . . ? C11 C12 H12 118.1 . . ? C13 C12 H12 118.1 . . ? O4 C13 C12 124.6(2) . . ? O4 C13 C14 116.54(19) . . ? C12 C13 C14 118.8(2) . . ? 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 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C16 C17 124.46(18) . . ? O5 C16 C15 115.54(18) . . ? C17 C16 C15 120.00(19) . . ? C16 C17 C18 123.46(19) . . ? C16 C17 H17 118.3 . . ? C18 C17 H17 118.3 . . ? O6 C18 C17 125.15(19) . . ? O6 C18 C19 116.60(18) . . ? C17 C18 C19 118.25(19) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? #===END data_2 _database_code_depnum_ccdc_archive 'CCDC 752072' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H48 N4 O12 Tb2' _chemical_formula_weight 1070.64 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' Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2276(6) _cell_length_b 9.8575(10) _cell_length_c 12.4828(13) _cell_angle_alpha 106.977(5) _cell_angle_beta 97.121(6) _cell_angle_gamma 96.480(6) _cell_volume 1064.22(17) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 28924 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 25.68 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.671 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 530 _exptl_absorpt_coefficient_mu 3.358 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.622 _exptl_absorpt_correction_T_max 0.818 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 area-detector diffractometer' _diffrn_measurement_method 'two \f and four \w scans with 2\% steps (372 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 28924 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3981 _reflns_number_gt 3569 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by Patterson map interpretation and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (CH) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0455P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _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 3981 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0744 _refine_ls_wR_factor_gt 0.0722 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.673 _refine_diff_density_min -1.499 _refine_diff_density_rms 0.127 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 Tb Tb 0.704144(18) 0.747256(19) 0.839968(15) 0.02370(8) Uani 1 1 d . . . O1 O 0.8204(3) 0.6672(3) 0.9801(2) 0.0308(6) Uani 1 1 d . . . O2 O 0.5426(3) 0.7479(3) 0.9690(2) 0.0286(6) Uani 1 1 d . . . O3 O 0.7857(3) 0.5459(3) 0.7291(3) 0.0319(7) Uani 1 1 d . . . O4 O 0.4946(3) 0.5917(3) 0.7272(2) 0.0324(7) Uani 1 1 d . . . O5 O 0.7941(3) 0.8270(3) 0.6986(2) 0.0320(7) Uani 1 1 d . . . O6 O 0.5465(3) 0.9002(3) 0.7913(2) 0.0283(6) Uani 1 1 d . . . N1 N 0.9889(3) 0.8373(3) 0.8854(3) 0.0257(7) Uani 1 1 d . . . N2 N 1.1963(3) 1.0071(3) 0.9993(3) 0.0266(7) Uani 1 1 d . . . C1 C 1.0503(4) 0.9567(4) 0.9679(3) 0.0228(8) Uani 1 1 d . . . C2 C 1.2853(5) 0.9274(5) 0.9405(4) 0.0315(9) Uani 1 1 d . . . H2 H 1.3868 0.9585 0.9588 0.038 Uiso 1 1 calc R . . C3 C 1.2323(5) 0.7999(5) 0.8530(4) 0.0322(9) Uani 1 1 d . . . H3 H 1.2959 0.7448 0.8139 0.039 Uiso 1 1 calc R . . C4 C 1.0814(4) 0.7595(4) 0.8274(4) 0.0290(9) Uani 1 1 d . . . H4 H 1.0419 0.6761 0.7683 0.035 Uiso 1 1 calc R . . C5 C 0.9095(5) 0.5941(6) 1.1370(4) 0.0441(12) Uani 1 1 d . . . H5A H 0.9409 0.5105 1.0899 0.066 Uiso 1 1 calc R . . H5B H 0.8732 0.5725 1.1999 0.066 Uiso 1 1 calc R . . H5C H 0.9917 0.6710 1.1648 0.066 Uiso 1 1 calc R . . C6 C 0.7871(5) 0.6389(5) 1.0676(4) 0.0334(10) Uani 1 1 d . . . C7 C 0.6482(5) 0.6454(5) 1.1026(4) 0.0351(10) Uani 1 1 d . . . H7 H 0.6320 0.6136 1.1639 0.042 Uiso 1 1 calc R . . C8 C 0.5334(5) 0.6967(4) 1.0507(4) 0.0305(9) Uani 1 1 d . . . C9 C 0.3891(5) 0.6979(5) 1.0955(4) 0.0380(10) Uani 1 1 d . . . H9A H 0.3760 0.7954 1.1305 0.057 Uiso 1 1 calc R . . H9B H 0.3902 0.6474 1.1507 0.057 Uiso 1 1 calc R . . H9C H 0.3090 0.6518 1.0340 0.057 Uiso 1 1 calc R . . C10 C 0.8359(5) 0.3475(5) 0.5867(4) 0.0467(12) Uani 1 1 d . . . H10A H 0.9133 0.4076 0.5697 0.070 Uiso 1 1 calc R . . H10B H 0.7843 0.2776 0.5177 0.070 Uiso 1 1 calc R . . H10C H 0.8781 0.2994 0.6368 0.070 Uiso 1 1 calc R . . C11 C 0.7286(5) 0.4392(5) 0.6437(4) 0.0328(10) Uani 1 1 d . . . C12 C 0.5774(5) 0.3994(5) 0.6003(4) 0.0339(10) Uani 1 1 d . . . H12 H 0.5472 0.3168 0.5385 0.041 Uiso 1 1 calc R . . C13 C 0.4697(5) 0.4770(5) 0.6448(4) 0.0298(9) Uani 1 1 d . . . C14 C 0.3089(5) 0.4208(5) 0.5928(4) 0.0397(11) Uani 1 1 d . . . H14A H 0.2712 0.3494 0.6250 0.059 Uiso 1 1 calc R . . H14B H 0.3009 0.3788 0.5122 0.059 Uiso 1 1 calc R . . H14C H 0.2527 0.4985 0.6084 0.059 Uiso 1 1 calc R . . C15 C 0.8784(5) 0.9487(5) 0.5762(4) 0.0402(11) Uani 1 1 d . . . H15A H 0.9635 1.0090 0.6269 0.060 Uiso 1 1 calc R . . H15B H 0.8376 0.9981 0.5267 0.060 Uiso 1 1 calc R . . H15C H 0.9070 0.8617 0.5318 0.060 Uiso 1 1 calc R . . C16 C 0.7635(5) 0.9126(5) 0.6445(4) 0.0325(10) Uani 1 1 d . . . C17 C 0.6323(5) 0.9715(5) 0.6423(4) 0.0336(10) Uani 1 1 d . . . H17 H 0.6130 1.0231 0.5919 0.040 Uiso 1 1 calc R . . C18 C 0.5295(4) 0.9559(4) 0.7124(4) 0.0301(9) Uani 1 1 d . . . C19 C 0.3841(5) 1.0110(5) 0.6935(4) 0.0372(10) Uani 1 1 d . . . H19A H 0.3066 0.9312 0.6566 0.056 Uiso 1 1 calc R . . H19B H 0.3927 1.0723 0.6465 0.056 Uiso 1 1 calc R . . H19C H 0.3612 1.0644 0.7653 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 Tb 0.01962(13) 0.02521(12) 0.02587(13) 0.00798(8) 0.00334(8) 0.00220(8) O1 0.0297(16) 0.0365(16) 0.0310(17) 0.0170(14) 0.0059(12) 0.0070(12) O2 0.0245(15) 0.0309(15) 0.0303(16) 0.0094(13) 0.0067(12) 0.0015(11) O3 0.0279(16) 0.0275(15) 0.0362(18) 0.0054(13) 0.0017(13) 0.0039(12) O4 0.0238(15) 0.0335(16) 0.0317(17) 0.0021(14) 0.0007(12) -0.0036(12) O5 0.0290(16) 0.0411(17) 0.0322(17) 0.0177(14) 0.0085(12) 0.0105(13) O6 0.0239(15) 0.0318(15) 0.0315(16) 0.0125(13) 0.0053(12) 0.0061(12) N1 0.0200(17) 0.0268(18) 0.0282(19) 0.0072(15) 0.0011(14) 0.0017(13) N2 0.0206(17) 0.0271(18) 0.032(2) 0.0091(15) 0.0055(14) 0.0041(13) C1 0.0171(19) 0.028(2) 0.027(2) 0.0139(17) 0.0050(16) 0.0030(15) C2 0.021(2) 0.032(2) 0.039(3) 0.0061(19) 0.0060(18) 0.0044(17) C3 0.028(2) 0.033(2) 0.035(2) 0.0080(19) 0.0081(18) 0.0087(18) C4 0.025(2) 0.029(2) 0.031(2) 0.0073(18) 0.0039(17) 0.0044(17) C5 0.045(3) 0.052(3) 0.042(3) 0.024(2) 0.004(2) 0.015(2) C6 0.040(3) 0.028(2) 0.034(3) 0.0121(19) 0.0065(19) 0.0061(18) C7 0.041(3) 0.034(2) 0.032(2) 0.012(2) 0.0089(19) 0.0049(19) C8 0.034(2) 0.026(2) 0.028(2) 0.0035(18) 0.0082(18) -0.0007(17) C9 0.035(3) 0.042(3) 0.040(3) 0.015(2) 0.012(2) 0.003(2) C10 0.047(3) 0.040(3) 0.041(3) -0.003(2) -0.002(2) 0.016(2) C11 0.038(2) 0.028(2) 0.031(2) 0.0085(19) 0.0018(19) 0.0096(18) C12 0.039(3) 0.028(2) 0.029(2) 0.0034(18) -0.0008(19) 0.0010(18) C13 0.030(2) 0.031(2) 0.027(2) 0.0121(19) 0.0042(17) -0.0046(17) C14 0.035(3) 0.045(3) 0.032(3) 0.007(2) 0.004(2) -0.006(2) C15 0.035(3) 0.048(3) 0.043(3) 0.024(2) 0.010(2) 0.002(2) C16 0.038(3) 0.032(2) 0.024(2) 0.0062(19) 0.0026(18) 0.0020(18) C17 0.036(2) 0.036(2) 0.031(2) 0.013(2) 0.0026(19) 0.0083(19) C18 0.028(2) 0.026(2) 0.032(2) 0.0050(18) -0.0027(17) 0.0039(16) C19 0.035(3) 0.038(2) 0.037(3) 0.010(2) 0.001(2) 0.012(2) _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 Tb O1 2.317(3) . ? Tb O2 2.325(3) . ? Tb O3 2.327(3) . ? Tb O5 2.334(3) . ? Tb O4 2.338(3) . ? Tb O6 2.360(3) . ? Tb N1 2.612(3) . ? Tb N2 2.634(3) 2_777 ? O1 C6 1.268(5) . ? O2 C8 1.271(5) . ? O3 C11 1.265(5) . ? O4 C13 1.262(5) . ? O5 C16 1.260(5) . ? O6 C18 1.262(5) . ? N1 C1 1.329(5) . ? N1 C4 1.348(5) . ? N2 C2 1.338(5) . ? N2 C1 1.349(5) . ? N2 Tb 2.633(3) 2_777 ? C1 C1 1.481(8) 2_777 ? C2 C3 1.392(6) . ? C2 H2 0.9300 . ? C3 C4 1.375(6) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 C6 1.521(6) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.406(6) . ? C7 C8 1.393(6) . ? C7 H7 0.9300 . ? C8 C9 1.507(6) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.518(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.400(6) . ? C12 C13 1.393(6) . ? C12 H12 0.9300 . ? C13 C14 1.515(6) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.514(6) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.402(6) . ? C17 C18 1.394(6) . ? C17 H17 0.9300 . ? C18 C19 1.521(6) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Tb O2 73.19(10) . . ? O1 Tb O3 79.58(10) . . ? O2 Tb O3 125.85(10) . . ? O1 Tb O5 131.64(10) . . ? O2 Tb O5 152.20(10) . . ? O3 Tb O5 76.93(10) . . ? O1 Tb O4 114.50(10) . . ? O2 Tb O4 77.27(10) . . ? O3 Tb O4 72.91(10) . . ? O5 Tb O4 97.98(10) . . ? O1 Tb O6 148.06(10) . . ? O2 Tb O6 80.30(10) . . ? O3 Tb O6 131.47(10) . . ? O5 Tb O6 72.04(9) . . ? O4 Tb O6 75.51(10) . . ? O1 Tb N1 67.98(10) . . ? O2 Tb N1 127.38(10) . . ? O3 Tb N1 80.25(10) . . ? O5 Tb N1 66.76(10) . . ? O4 Tb N1 151.71(11) . . ? O6 Tb N1 118.30(10) . . ? O1 Tb N2 79.29(10) . 2_777 ? O2 Tb N2 77.45(10) . 2_777 ? O3 Tb N2 141.26(10) . 2_777 ? O5 Tb N2 93.74(11) . 2_777 ? O4 Tb N2 145.78(10) . 2_777 ? O6 Tb N2 77.81(10) . 2_777 ? N1 Tb N2 61.80(10) . 2_777 ? C6 O1 Tb 136.3(3) . . ? C8 O2 Tb 135.9(3) . . ? C11 O3 Tb 135.6(3) . . ? C13 O4 Tb 136.1(3) . . ? C16 O5 Tb 137.4(3) . . ? C18 O6 Tb 135.2(3) . . ? C1 N1 C4 116.8(3) . . ? C1 N1 Tb 122.7(3) . . ? C4 N1 Tb 120.5(3) . . ? C2 N2 C1 115.6(4) . . ? C2 N2 Tb 122.8(3) . 2_777 ? C1 N2 Tb 121.5(3) . 2_777 ? N1 C1 N2 126.1(4) . . ? N1 C1 C1 117.3(4) . 2_777 ? N2 C1 C1 116.5(4) . 2_777 ? N2 C2 C3 122.8(4) . . ? N2 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C4 C3 C2 116.6(4) . . ? C4 C3 H3 121.7 . . ? C2 C3 H3 121.7 . . ? N1 C4 C3 122.0(4) . . ? N1 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C6 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O1 C6 C7 124.9(4) . . ? O1 C6 C5 115.6(4) . . ? C7 C6 C5 119.5(4) . . ? C8 C7 C6 123.8(4) . . ? C8 C7 H7 118.1 . . ? C6 C7 H7 118.1 . . ? O2 C8 C7 124.4(4) . . ? O2 C8 C9 116.6(4) . . ? C7 C8 C9 119.0(4) . . ? 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 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 C12 125.5(4) . . ? O3 C11 C10 115.8(4) . . ? C12 C11 C10 118.7(4) . . ? C13 C12 C11 123.5(4) . . ? C13 C12 H12 118.3 . . ? C11 C12 H12 118.3 . . ? O4 C13 C12 125.2(4) . . ? O4 C13 C14 116.2(4) . . ? C12 C13 C14 118.7(4) . . ? 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 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C16 C17 124.6(4) . . ? O5 C16 C15 115.7(4) . . ? C17 C16 C15 119.7(4) . . ? C18 C17 C16 122.7(4) . . ? C18 C17 H17 118.7 . . ? C16 C17 H17 118.7 . . ? O6 C18 C17 125.7(4) . . ? O6 C18 C19 116.6(4) . . ? C17 C18 C19 117.7(4) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? #===END data_3 _database_code_depnum_ccdc_archive 'CCDC 752073' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H48 N4 O12 Sm2' _chemical_formula_weight 1053.50 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 9.2497(7) _cell_length_b 9.9437(10) _cell_length_c 12.4584(13) _cell_angle_alpha 107.516(5) _cell_angle_beta 96.940(6) _cell_angle_gamma 95.639(6) _cell_volume 1073.71(18) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 31878 _cell_measurement_theta_min 2.17 _cell_measurement_theta_max 25.68 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 2.769 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.647 _exptl_absorpt_correction_T_max 0.737 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(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 area-detector diffractometer' _diffrn_measurement_method 'two \f and five \w scans with 2\% steps (406 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 31878 _diffrn_reflns_av_R_equivalents 0.0398 _diffrn_reflns_av_sigmaI/netI 0.0518 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.68 _reflns_number_total 4046 _reflns_number_gt 3585 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1999)' _computing_publication_material 'SHELXTL (Sheldrick, 1999); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by Patterson map interpretation and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (CH) or 1.5 (CH~3~) times that of the parent atom. 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^)+(0.0434P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _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 4046 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0761 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.050 _refine_diff_density_min -1.092 _refine_diff_density_rms 0.116 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 Sm Sm 0.70445(2) 0.74542(2) 0.838459(16) 0.02564(9) Uani 1 1 d . . . O1 O 0.8224(3) 0.6657(3) 0.9825(2) 0.0328(7) Uani 1 1 d . . . O2 O 0.5430(3) 0.7481(3) 0.9719(2) 0.0311(6) Uani 1 1 d . . . O3 O 0.7912(3) 0.5455(3) 0.7216(2) 0.0344(7) Uani 1 1 d . . . O4 O 0.4966(3) 0.5830(3) 0.7256(2) 0.0345(7) Uani 1 1 d . . . O5 O 0.7970(3) 0.8333(3) 0.6990(2) 0.0346(7) Uani 1 1 d . . . O6 O 0.5412(3) 0.8965(3) 0.7880(2) 0.0307(6) Uani 1 1 d . . . N1 N 0.9903(3) 0.8360(4) 0.8857(3) 0.0269(7) Uani 1 1 d . . . N2 N 1.1962(3) 1.0048(3) 0.9987(3) 0.0272(7) Uani 1 1 d . . . C1 C 1.0514(4) 0.9560(4) 0.9690(3) 0.0282(9) Uani 1 1 d . . . C2 C 1.2850(4) 0.9244(5) 0.9403(4) 0.0365(10) Uani 1 1 d . . . H2 H 1.3858 0.9547 0.9577 0.044 Uiso 1 1 calc R . . C3 C 1.2324(5) 0.7953(5) 0.8533(3) 0.0336(9) Uani 1 1 d . . . H3 H 1.2957 0.7390 0.8141 0.040 Uiso 1 1 calc R . . C4 C 1.0839(4) 0.7572(4) 0.8293(3) 0.0291(9) Uani 1 1 d . . . H4 H 1.0454 0.6729 0.7714 0.035 Uiso 1 1 calc R . . C5 C 0.9105(5) 0.5915(6) 1.1377(4) 0.0449(12) Uani 1 1 d . . . H5A H 0.9426 0.5085 1.0896 0.067 Uiso 1 1 calc R . . H5B H 0.8747 0.5698 1.2006 0.067 Uiso 1 1 calc R . . H5C H 0.9916 0.6674 1.1659 0.067 Uiso 1 1 calc R . . C6 C 0.7883(5) 0.6368(5) 1.0696(4) 0.0349(10) Uani 1 1 d . . . C7 C 0.6499(5) 0.6429(5) 1.1029(4) 0.0349(10) Uani 1 1 d . . . H7 H 0.6332 0.6092 1.1629 0.042 Uiso 1 1 calc R . . C8 C 0.5342(5) 0.6956(4) 1.0531(3) 0.0321(9) Uani 1 1 d . . . C9 C 0.3901(5) 0.6960(5) 1.0982(4) 0.0417(11) Uani 1 1 d . . . H9A H 0.3758 0.7925 1.1347 0.062 Uiso 1 1 calc R . . H9B H 0.3918 0.6447 1.1523 0.062 Uiso 1 1 calc R . . H9C H 0.3111 0.6512 1.0362 0.062 Uiso 1 1 calc R . . C10 C 0.8463(5) 0.3519(6) 0.5756(4) 0.0504(13) Uani 1 1 d . . . H10A H 0.9227 0.4151 0.5627 0.076 Uiso 1 1 calc R . . H10B H 0.7972 0.2866 0.5039 0.076 Uiso 1 1 calc R . . H10C H 0.8885 0.2996 0.6219 0.076 Uiso 1 1 calc R . . C11 C 0.7362(5) 0.4379(5) 0.6362(4) 0.0350(10) Uani 1 1 d . . . C12 C 0.5860(5) 0.3969(5) 0.5946(4) 0.0354(10) Uani 1 1 d . . . H12 H 0.5580 0.3160 0.5312 0.042 Uiso 1 1 calc R . . C13 C 0.4755(5) 0.4689(5) 0.6416(3) 0.0340(10) Uani 1 1 d . . . C14 C 0.3170(5) 0.4077(5) 0.5911(4) 0.0403(11) Uani 1 1 d . . . H14A H 0.2854 0.3346 0.6223 0.060 Uiso 1 1 calc R . . H14B H 0.3087 0.3678 0.5098 0.060 Uiso 1 1 calc R . . H14C H 0.2563 0.4819 0.6090 0.060 Uiso 1 1 calc R . . C15 C 0.8789(5) 0.9573(5) 0.5795(4) 0.0443(11) Uani 1 1 d . . . H15A H 0.9651 1.0103 0.6316 0.066 Uiso 1 1 calc R . . H15B H 0.8407 1.0144 0.5358 0.066 Uiso 1 1 calc R . . H15C H 0.9040 0.8720 0.5290 0.066 Uiso 1 1 calc R . . C16 C 0.7635(5) 0.9183(5) 0.6456(3) 0.0323(9) Uani 1 1 d . . . C17 C 0.6309(5) 0.9749(5) 0.6439(4) 0.0363(10) Uani 1 1 d . . . H17 H 0.6121 1.0281 0.5952 0.044 Uiso 1 1 calc R . . C18 C 0.5256(4) 0.9562(4) 0.7110(3) 0.0326(9) Uani 1 1 d . . . C19 C 0.3803(5) 1.0104(5) 0.6930(4) 0.0412(11) Uani 1 1 d . . . H19A H 0.3040 0.9310 0.6575 0.062 Uiso 1 1 calc R . . H19B H 0.3869 1.0694 0.6449 0.062 Uiso 1 1 calc R . . H19C H 0.3578 1.0650 0.7653 0.062 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 Sm 0.02297(13) 0.02580(13) 0.02799(12) 0.00904(9) 0.00336(8) 0.00196(8) O1 0.0312(15) 0.0377(18) 0.0356(16) 0.0196(13) 0.0055(12) 0.0083(13) O2 0.0302(15) 0.0327(17) 0.0317(15) 0.0114(13) 0.0084(12) 0.0019(12) O3 0.0334(16) 0.0273(16) 0.0371(16) 0.0028(13) 0.0025(13) 0.0065(12) O4 0.0284(15) 0.0346(18) 0.0335(16) 0.0049(14) 0.0005(12) -0.0047(12) O5 0.0340(16) 0.0419(19) 0.0354(16) 0.0213(14) 0.0087(13) 0.0076(13) O6 0.0275(14) 0.0305(16) 0.0359(15) 0.0127(13) 0.0050(12) 0.0062(12) N1 0.0237(17) 0.0297(19) 0.0266(17) 0.0095(14) 0.0019(13) 0.0003(14) N2 0.0245(17) 0.0263(19) 0.0286(17) 0.0073(14) 0.0022(14) 0.0010(14) C1 0.028(2) 0.029(2) 0.031(2) 0.0143(18) 0.0034(17) 0.0060(17) C2 0.019(2) 0.043(3) 0.045(3) 0.009(2) 0.0044(18) 0.0053(18) C3 0.030(2) 0.035(2) 0.034(2) 0.0069(19) 0.0076(18) 0.0057(18) C4 0.032(2) 0.022(2) 0.030(2) 0.0051(17) 0.0027(17) 0.0026(16) C5 0.051(3) 0.055(3) 0.039(2) 0.027(2) 0.006(2) 0.019(2) C6 0.043(3) 0.026(2) 0.035(2) 0.0099(19) 0.004(2) 0.0066(19) C7 0.042(3) 0.034(3) 0.032(2) 0.0137(19) 0.0111(19) 0.0053(19) C8 0.035(2) 0.025(2) 0.031(2) 0.0035(17) 0.0099(18) -0.0031(17) C9 0.042(3) 0.041(3) 0.042(3) 0.011(2) 0.016(2) 0.003(2) C10 0.048(3) 0.047(3) 0.044(3) -0.004(2) -0.001(2) 0.020(2) C11 0.042(3) 0.030(2) 0.033(2) 0.0094(19) 0.0023(19) 0.0083(19) C12 0.040(3) 0.029(2) 0.032(2) 0.0069(19) 0.0001(19) 0.0010(19) C13 0.037(2) 0.035(3) 0.030(2) 0.015(2) 0.0006(18) -0.0083(19) C14 0.035(2) 0.047(3) 0.034(2) 0.011(2) 0.0014(19) -0.007(2) C15 0.045(3) 0.047(3) 0.046(3) 0.026(2) 0.008(2) 0.001(2) C16 0.037(2) 0.031(2) 0.025(2) 0.0058(18) 0.0030(17) -0.0009(18) C17 0.042(3) 0.035(3) 0.035(2) 0.0148(19) 0.0042(19) 0.0102(19) C18 0.034(2) 0.027(2) 0.033(2) 0.0056(18) -0.0036(18) 0.0058(17) C19 0.042(3) 0.040(3) 0.043(3) 0.014(2) -0.001(2) 0.016(2) _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 Sm O3 2.360(3) . ? Sm O2 2.361(3) . ? Sm O1 2.365(3) . ? Sm O5 2.375(3) . ? Sm O4 2.377(3) . ? Sm O6 2.391(3) . ? Sm N1 2.643(3) . ? Sm N2 2.683(3) 2_777 ? O1 C6 1.269(5) . ? O2 C8 1.277(5) . ? O3 C11 1.270(5) . ? O4 C13 1.270(5) . ? O5 C16 1.262(5) . ? O6 C18 1.273(5) . ? N1 C1 1.342(5) . ? N1 C4 1.344(5) . ? N2 C2 1.329(5) . ? N2 C1 1.346(5) . ? N2 Sm 2.683(3) 2_777 ? C1 C1 1.484(8) 2_777 ? C2 C3 1.404(6) . ? C2 H2 0.9300 . ? C3 C4 1.360(6) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 C6 1.516(6) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.394(6) . ? C7 C8 1.396(6) . ? C7 H7 0.9300 . ? C8 C9 1.507(6) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.518(6) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.398(6) . ? C12 C13 1.391(6) . ? C12 H12 0.9300 . ? C13 C14 1.512(6) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.513(6) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.399(6) . ? C17 C18 1.392(6) . ? C17 H17 0.9300 . ? C18 C19 1.513(6) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 Sm O2 127.35(10) . . ? O3 Sm O1 81.12(10) . . ? O2 Sm O1 72.26(9) . . ? O3 Sm O5 77.25(10) . . ? O2 Sm O5 151.44(10) . . ? O1 Sm O5 131.85(9) . . ? O3 Sm O4 72.18(10) . . ? O2 Sm O4 77.55(10) . . ? O1 Sm O4 112.77(10) . . ? O5 Sm O4 100.68(10) . . ? O3 Sm O6 129.91(10) . . ? O2 Sm O6 80.65(9) . . ? O1 Sm O6 148.02(9) . . ? O5 Sm O6 71.36(9) . . ? O4 Sm O6 76.45(10) . . ? O3 Sm N1 80.09(10) . . ? O2 Sm N1 126.38(10) . . ? O1 Sm N1 68.04(10) . . ? O5 Sm N1 66.17(10) . . ? O4 Sm N1 151.52(10) . . ? O6 Sm N1 118.88(10) . . ? O3 Sm N2 140.77(9) . 2_777 ? O2 Sm N2 77.67(10) . 2_777 ? O1 Sm N2 79.51(10) . 2_777 ? O5 Sm N2 90.98(10) . 2_777 ? O4 Sm N2 147.03(10) . 2_777 ? O6 Sm N2 78.36(10) . 2_777 ? N1 Sm N2 61.07(10) . 2_777 ? C6 O1 Sm 136.5(3) . . ? C8 O2 Sm 135.9(3) . . ? C11 O3 Sm 136.2(3) . . ? C13 O4 Sm 135.9(3) . . ? C16 O5 Sm 137.4(3) . . ? C18 O6 Sm 135.8(3) . . ? C1 N1 C4 116.2(3) . . ? C1 N1 Sm 123.5(2) . . ? C4 N1 Sm 120.2(3) . . ? C2 N2 C1 116.0(3) . . ? C2 N2 Sm 122.7(3) . 2_777 ? C1 N2 Sm 121.3(2) . 2_777 ? N1 C1 N2 125.9(3) . . ? N1 C1 C1 116.5(4) . 2_777 ? N2 C1 C1 117.6(5) . 2_777 ? N2 C2 C3 122.6(4) . . ? N2 C2 H2 118.7 . . ? C3 C2 H2 118.7 . . ? C4 C3 C2 116.5(4) . . ? C4 C3 H3 121.8 . . ? C2 C3 H3 121.8 . . ? N1 C4 C3 122.8(4) . . ? N1 C4 H4 118.6 . . ? C3 C4 H4 118.6 . . ? C6 C5 H5A 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C6 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O1 C6 C7 124.5(4) . . ? O1 C6 C5 115.1(4) . . ? C7 C6 C5 120.4(4) . . ? C6 C7 C8 125.1(4) . . ? C6 C7 H7 117.4 . . ? C8 C7 H7 117.4 . . ? O2 C8 C7 124.0(4) . . ? O2 C8 C9 116.6(4) . . ? C7 C8 C9 119.4(4) . . ? 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 . . ? C11 C10 H10A 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C11 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 C12 125.1(4) . . ? O3 C11 C10 115.6(4) . . ? C12 C11 C10 119.3(4) . . ? C13 C12 C11 124.4(4) . . ? C13 C12 H12 117.8 . . ? C11 C12 H12 117.8 . . ? O4 C13 C12 125.1(4) . . ? O4 C13 C14 116.4(4) . . ? C12 C13 C14 118.5(4) . . ? 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 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C16 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O5 C16 C17 124.7(4) . . ? O5 C16 C15 115.1(4) . . ? C17 C16 C15 120.2(4) . . ? C18 C17 C16 123.8(4) . . ? C18 C17 H17 118.1 . . ? C16 C17 H17 118.1 . . ? O6 C18 C17 125.1(4) . . ? O6 C18 C19 116.2(4) . . ? C17 C18 C19 118.7(4) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ?