# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Xigeng Zhou' _publ_contact_author_email XGZHOU@FUDAN.EDU.CN _publ_section_title ; Isocyanate diinsertion into the N?H bond of 2-pyridylamino ligand of organolanthanides ; loop_ _publ_author_name 'Xigeng Zhou.' 'Xiaoqing Li.' 'Yan Sun.' 'Xu Wang.' 'Lin-Hong Weng.' ; Zheng-Xing Zhang ; # Attachment '09sy-Dalton.cif' data_f71128b _database_code_depnum_ccdc_archive 'CCDC 723134' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H33 N4 O3 Yb' _chemical_formula_weight 706.67 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Yb Yb -0.3850 5.5486 '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 9.809(4) _cell_length_b 11.794(5) _cell_length_c 26.003(10) _cell_angle_alpha 90.00 _cell_angle_beta 94.882(5) _cell_angle_gamma 90.00 _cell_volume 2997(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 947 _cell_measurement_theta_min 2.334 _cell_measurement_theta_max 26.235 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1412 _exptl_absorpt_coefficient_mu 3.160 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4508 _exptl_absorpt_correction_T_max 0.6486 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '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_% ? _diffrn_reflns_number 12228 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5259 _reflns_number_gt 4595 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0184P)^2^+5.5854P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00242(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5259 _refine_ls_number_parameters 374 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0717 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.151 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Yb1 Yb 1.055307(18) 0.584022(16) 0.157901(7) 0.03385(9) Uani 1 1 d . . . N1 N 0.9445(4) 0.7417(3) 0.19625(14) 0.0430(9) Uani 1 1 d . . . N2 N 0.8212(4) 0.5924(3) 0.16902(14) 0.0395(9) Uani 1 1 d . . . N3 N 0.7233(4) 0.4407(3) 0.12129(15) 0.0400(9) Uani 1 1 d . . . N4 N 0.8303(4) 0.2698(3) 0.10963(19) 0.0517(11) Uani 1 1 d D . . H4' H 0.751(3) 0.244(4) 0.101(2) 0.062 Uiso 1 1 d D . . O1 O 0.5933(3) 0.5912(3) 0.13971(16) 0.0568(9) Uani 1 1 d . . . O2 O 0.9581(3) 0.4163(3) 0.13704(14) 0.0497(8) Uani 1 1 d . . . C1 C 1.1070(10) 0.5653(6) 0.0616(2) 0.082(2) Uani 1 1 d . . . H1 H 1.1087 0.4925 0.0478 0.098 Uiso 1 1 calc R . . C2 C 1.2139(8) 0.6203(8) 0.0843(3) 0.085(2) Uani 1 1 d . . . H2 H 1.3025 0.5920 0.0895 0.102 Uiso 1 1 calc R . . C3 C 1.1729(9) 0.7234(6) 0.0983(2) 0.082(2) Uani 1 1 d . . . H3 H 1.2291 0.7785 0.1146 0.098 Uiso 1 1 calc R . . C4 C 1.0361(9) 0.7352(6) 0.0849(2) 0.081(2) Uani 1 1 d . . . H4 H 0.9827 0.7985 0.0903 0.098 Uiso 1 1 calc R . . C5 C 0.9925(8) 0.6341(8) 0.0617(2) 0.088(2) Uani 1 1 d . . . H5 H 0.9038 0.6160 0.0489 0.106 Uiso 1 1 calc R . . C6 C 1.1322(7) 0.4661(8) 0.2414(3) 0.082(2) Uani 1 1 d . . . H6 H 1.0707 0.4122 0.2515 0.099 Uiso 1 1 calc R . . C7 C 1.1396(9) 0.5780(10) 0.2570(2) 0.101(3) Uani 1 1 d . . . H7 H 1.0852 0.6133 0.2799 0.121 Uiso 1 1 calc R . . C8 C 1.2449(8) 0.6279(6) 0.2319(3) 0.084(2) Uani 1 1 d . . . H8 H 1.2725 0.7032 0.2345 0.101 Uiso 1 1 calc R . . C9 C 1.3000(6) 0.5454(7) 0.2027(3) 0.0715(18) Uani 1 1 d . . . H9 H 1.3729 0.5552 0.1825 0.086 Uiso 1 1 calc R . . C10 C 1.2314(6) 0.4485(6) 0.2082(2) 0.0667(16) Uani 1 1 d . . . H10 H 1.2484 0.3803 0.1920 0.080 Uiso 1 1 calc R . . C11 C 0.8185(5) 0.6963(4) 0.19385(17) 0.0389(10) Uani 1 1 d . . . C12 C 0.7121(5) 0.7489(5) 0.2170(2) 0.0562(13) Uani 1 1 d . . . H12 H 0.6257 0.7161 0.2158 0.067 Uiso 1 1 calc R . . C13 C 0.7388(6) 0.8509(5) 0.2415(2) 0.0644(16) Uani 1 1 d . . . H13 H 0.6697 0.8876 0.2573 0.077 Uiso 1 1 calc R . . C14 C 0.8668(6) 0.8992(5) 0.2427(2) 0.0633(15) Uani 1 1 d . . . H14 H 0.8847 0.9688 0.2587 0.076 Uiso 1 1 calc R . . C15 C 0.9668(6) 0.8422(4) 0.2199(2) 0.0528(13) Uani 1 1 d . . . H15 H 1.0537 0.8742 0.2207 0.063 Uiso 1 1 calc R . . C16 C 0.7071(5) 0.5494(4) 0.14461(18) 0.0384(10) Uani 1 1 d . . . C17 C 0.6027(5) 0.3937(4) 0.0923(2) 0.0438(11) Uani 1 1 d . . . C18 C 0.5975(6) 0.3928(5) 0.0392(2) 0.0589(14) Uani 1 1 d . . . H18 H 0.6702 0.4210 0.0224 0.071 Uiso 1 1 calc R . . C19 C 0.4830(7) 0.3496(5) 0.0113(3) 0.0748(18) Uani 1 1 d . . . H19 H 0.4800 0.3465 -0.0245 0.090 Uiso 1 1 calc R . . C20 C 0.3752(7) 0.3119(6) 0.0357(3) 0.0755(19) Uani 1 1 d . . . H20 H 0.2977 0.2848 0.0164 0.091 Uiso 1 1 calc R . . C21 C 0.3790(6) 0.3132(5) 0.0881(3) 0.0743(19) Uani 1 1 d . . . H21 H 0.3045 0.2867 0.1044 0.089 Uiso 1 1 calc R . . C22 C 0.4947(5) 0.3541(5) 0.1176(2) 0.0562(14) Uani 1 1 d . . . H22 H 0.4984 0.3545 0.1535 0.067 Uiso 1 1 calc R . . C23 C 0.8427(5) 0.3771(4) 0.12327(18) 0.0395(10) Uani 1 1 d . . . C24 C 0.9440(5) 0.1993(4) 0.1011(2) 0.0444(11) Uani 1 1 d . . . C25 C 0.9754(6) 0.1812(5) 0.0511(2) 0.0625(15) Uani 1 1 d . . . H25 H 0.9266 0.2191 0.0241 0.075 Uiso 1 1 calc R . . C26 C 1.0777(7) 0.1081(6) 0.0409(3) 0.0751(18) Uani 1 1 d . . . H26 H 1.0983 0.0963 0.0071 0.090 Uiso 1 1 calc R . . C27 C 1.1498(7) 0.0524(5) 0.0805(3) 0.0750(19) Uani 1 1 d . . . H27 H 1.2185 0.0018 0.0735 0.090 Uiso 1 1 calc R . . C28 C 1.1214(7) 0.0705(5) 0.1296(3) 0.078(2) Uani 1 1 d . . . H28 H 1.1717 0.0331 0.1564 0.094 Uiso 1 1 calc R . . C29 C 1.0176(6) 0.1448(5) 0.1406(2) 0.0629(15) Uani 1 1 d . . . H29 H 0.9985 0.1572 0.1746 0.075 Uiso 1 1 calc R . . O3 O 0.6447(7) 1.0809(5) 0.0903(3) 0.130(2) Uani 1 1 d . . . C30 C 0.698(2) 0.9904(15) 0.0730(10) 0.42(2) Uani 1 1 d U . . H30A H 0.7937 0.9896 0.0855 0.498 Uiso 1 1 calc R . . H30B H 0.6936 0.9970 0.0357 0.498 Uiso 1 1 calc R . . C31 C 0.6434(15) 0.8864(10) 0.0844(6) 0.168(5) Uani 1 1 d U . . H31A H 0.6308 0.8382 0.0541 0.202 Uiso 1 1 calc R . . H31B H 0.6993 0.8474 0.1114 0.202 Uiso 1 1 calc R . . C32 C 0.5235(12) 0.9204(10) 0.1004(9) 0.246(11) Uani 1 1 d U . . H32A H 0.4931 0.8715 0.1271 0.295 Uiso 1 1 calc R . . H32B H 0.4526 0.9259 0.0721 0.295 Uiso 1 1 calc R . . C33 C 0.567(2) 1.0328(13) 0.1206(7) 0.267(11) Uani 1 1 d U . . H33A H 0.4865 1.0797 0.1240 0.321 Uiso 1 1 calc R . . H33B H 0.6146 1.0245 0.1546 0.321 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 Yb1 0.02947(12) 0.03880(13) 0.03323(12) -0.00143(9) 0.00231(7) -0.00062(9) N1 0.040(2) 0.047(2) 0.041(2) -0.0154(19) 0.0007(16) -0.0025(19) N2 0.0314(19) 0.042(2) 0.045(2) -0.0123(18) 0.0043(16) -0.0032(17) N3 0.032(2) 0.035(2) 0.051(2) -0.0077(17) -0.0006(17) -0.0013(15) N4 0.038(2) 0.036(2) 0.080(3) -0.013(2) 0.000(2) -0.0033(18) O1 0.0345(19) 0.046(2) 0.088(3) -0.0152(19) -0.0035(17) 0.0058(16) O2 0.0356(18) 0.0386(17) 0.074(2) -0.0099(17) -0.0008(16) 0.0013(15) C1 0.132(7) 0.072(5) 0.045(3) -0.004(3) 0.028(4) 0.006(5) C2 0.074(5) 0.125(7) 0.061(4) 0.018(4) 0.032(4) 0.014(5) C3 0.107(6) 0.076(5) 0.065(4) 0.014(4) 0.018(4) -0.043(4) C4 0.120(6) 0.071(5) 0.056(4) 0.028(3) 0.028(4) 0.035(4) C5 0.078(5) 0.139(7) 0.044(3) 0.031(4) -0.011(3) -0.027(5) C6 0.047(4) 0.126(6) 0.071(4) 0.049(5) -0.010(3) -0.006(4) C7 0.093(6) 0.170(9) 0.035(3) -0.003(5) -0.012(3) 0.059(6) C8 0.089(5) 0.075(4) 0.079(5) -0.003(4) -0.048(4) -0.006(4) C9 0.034(3) 0.106(5) 0.072(4) 0.023(4) -0.007(3) 0.002(3) C10 0.056(4) 0.070(4) 0.071(4) 0.011(3) -0.014(3) 0.016(3) C11 0.036(2) 0.045(3) 0.035(2) -0.006(2) 0.0022(19) 0.004(2) C12 0.041(3) 0.068(3) 0.060(3) -0.021(3) 0.007(2) 0.002(3) C13 0.059(4) 0.070(4) 0.065(4) -0.025(3) 0.008(3) 0.018(3) C14 0.068(4) 0.060(4) 0.061(3) -0.027(3) 0.000(3) 0.004(3) C15 0.050(3) 0.056(3) 0.053(3) -0.016(3) 0.001(2) -0.008(2) C16 0.033(3) 0.036(2) 0.048(3) 0.002(2) 0.009(2) -0.0022(19) C17 0.037(3) 0.032(3) 0.061(3) -0.009(2) -0.004(2) -0.0013(19) C18 0.064(4) 0.059(4) 0.053(3) 0.001(3) -0.003(3) -0.013(3) C19 0.074(5) 0.063(4) 0.081(4) -0.007(3) -0.027(4) -0.009(3) C20 0.057(4) 0.068(4) 0.096(5) -0.028(4) -0.024(4) 0.003(3) C21 0.044(3) 0.067(4) 0.112(6) -0.026(4) 0.011(3) -0.015(3) C22 0.043(3) 0.057(3) 0.070(4) -0.018(3) 0.010(3) -0.010(2) C23 0.038(3) 0.038(2) 0.043(3) 0.001(2) 0.006(2) 0.000(2) C24 0.041(3) 0.033(2) 0.059(3) -0.006(2) 0.000(2) -0.003(2) C25 0.066(4) 0.062(4) 0.060(4) 0.007(3) 0.009(3) 0.005(3) C26 0.076(4) 0.073(4) 0.079(4) -0.009(3) 0.025(4) 0.007(3) C27 0.060(4) 0.047(3) 0.120(6) -0.020(4) 0.016(4) 0.004(3) C28 0.070(4) 0.059(4) 0.100(5) 0.010(4) -0.026(4) 0.013(3) C29 0.068(4) 0.067(4) 0.051(3) -0.002(3) -0.006(3) 0.007(3) O3 0.110(5) 0.078(4) 0.209(8) -0.019(5) 0.049(5) -0.026(3) C30 0.48(3) 0.187(15) 0.64(4) -0.26(2) 0.44(3) -0.230(19) C31 0.166(12) 0.110(9) 0.227(15) -0.008(9) 0.010(11) 0.003(9) C32 0.081(7) 0.103(9) 0.55(3) 0.010(13) 0.028(14) -0.015(7) C33 0.40(3) 0.148(13) 0.28(2) -0.066(13) 0.20(2) -0.103(16) _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 Yb1 O2 2.242(3) . ? Yb1 N2 2.341(4) . ? Yb1 N1 2.412(4) . ? Yb1 C5 2.592(6) . ? Yb1 C3 2.597(6) . ? Yb1 C4 2.599(6) . ? Yb1 C2 2.604(6) . ? Yb1 C1 2.607(6) . ? Yb1 C8 2.611(6) . ? Yb1 C9 2.617(5) . ? Yb1 C10 2.619(5) . ? Yb1 C6 2.633(6) . ? N1 C11 1.344(6) . ? N1 C15 1.345(6) . ? N2 C16 1.339(6) . ? N2 C11 1.386(6) . ? N3 C23 1.388(6) . ? N3 C16 1.433(6) . ? N3 C17 1.457(6) . ? N4 C23 1.318(6) . ? N4 C24 1.423(6) . ? N4 H4' 0.84(2) . ? O1 C16 1.217(5) . ? O2 C23 1.246(6) . ? C1 C2 1.328(11) . ? C1 C5 1.386(11) . ? C1 H1 0.9300 . ? C2 C3 1.342(10) . ? C2 H2 0.9300 . ? C3 C4 1.364(10) . ? C3 H3 0.9300 . ? C4 C5 1.388(10) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C10 1.370(10) . ? C6 C7 1.381(11) . ? C6 H6 0.9300 . ? C7 C8 1.398(11) . ? C7 H7 0.9300 . ? C8 C9 1.372(10) . ? C8 H8 0.9300 . ? C9 C10 1.340(9) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.394(6) . ? C12 C13 1.376(7) . ? C12 H12 0.9300 . ? C13 C14 1.377(8) . ? C13 H13 0.9300 . ? C14 C15 1.366(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C18 1.375(7) . ? C17 C22 1.376(7) . ? C18 C19 1.382(8) . ? C18 H18 0.9300 . ? C19 C20 1.353(9) . ? C19 H19 0.9300 . ? C20 C21 1.361(9) . ? C20 H20 0.9300 . ? C21 C22 1.401(8) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C24 C29 1.365(7) . ? C24 C25 1.379(7) . ? C25 C26 1.366(8) . ? C25 H25 0.9300 . ? C26 C27 1.366(10) . ? C26 H26 0.9300 . ? C27 C28 1.348(10) . ? C27 H27 0.9300 . ? C28 C29 1.391(9) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? O3 C33 1.278(15) . ? O3 C30 1.286(17) . ? C30 C31 1.380(17) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.342(17) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.475(17) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Yb1 N2 70.46(12) . . ? O2 Yb1 N1 125.64(13) . . ? N2 Yb1 N1 55.61(12) . . ? O2 Yb1 C5 84.6(2) . . ? N2 Yb1 C5 87.4(2) . . ? N1 Yb1 C5 98.3(2) . . ? O2 Yb1 C3 127.99(19) . . ? N2 Yb1 C3 122.5(2) . . ? N1 Yb1 C3 89.8(2) . . ? C5 Yb1 C3 50.3(2) . . ? O2 Yb1 C4 115.2(2) . . ? N2 Yb1 C4 92.9(2) . . ? N1 Yb1 C4 76.44(18) . . ? C5 Yb1 C4 31.0(2) . . ? C3 Yb1 C4 30.4(2) . . ? O2 Yb1 C2 103.6(2) . . ? N2 Yb1 C2 137.6(2) . . ? N1 Yb1 C2 119.7(2) . . ? C5 Yb1 C2 50.3(2) . . ? C3 Yb1 C2 29.9(2) . . ? C4 Yb1 C2 50.3(2) . . ? O2 Yb1 C1 78.8(2) . . ? N2 Yb1 C1 113.3(2) . . ? N1 Yb1 C1 126.44(19) . . ? C5 Yb1 C1 30.9(2) . . ? C3 Yb1 C1 49.3(2) . . ? C4 Yb1 C1 50.6(2) . . ? C2 Yb1 C1 29.5(2) . . ? O2 Yb1 C8 127.92(19) . . ? N2 Yb1 C8 123.0(2) . . ? N1 Yb1 C8 82.0(2) . . ? C5 Yb1 C8 139.6(3) . . ? C3 Yb1 C8 89.4(3) . . ? C4 Yb1 C8 113.9(3) . . ? C2 Yb1 C8 94.4(3) . . ? C1 Yb1 C8 122.7(3) . . ? O2 Yb1 C9 108.02(19) . . ? N2 Yb1 C9 145.53(17) . . ? N1 Yb1 C9 112.2(2) . . ? C5 Yb1 C9 127.1(2) . . ? C3 Yb1 C9 86.5(2) . . ? C4 Yb1 C9 116.8(2) . . ? C2 Yb1 C9 76.9(2) . . ? C1 Yb1 C9 99.6(3) . . ? C8 Yb1 C9 30.4(2) . . ? O2 Yb1 C10 80.30(17) . . ? N2 Yb1 C10 125.19(18) . . ? N1 Yb1 C10 124.42(18) . . ? C5 Yb1 C10 135.5(3) . . ? C3 Yb1 C10 112.1(3) . . ? C4 Yb1 C10 141.9(2) . . ? C2 Yb1 C10 93.3(2) . . ? C1 Yb1 C10 104.7(2) . . ? C8 Yb1 C10 49.8(2) . . ? C9 Yb1 C10 29.65(19) . . ? O2 Yb1 C6 79.6(2) . . ? N2 Yb1 C6 97.80(18) . . ? N1 Yb1 C6 100.0(2) . . ? C5 Yb1 C6 160.6(3) . . ? C3 Yb1 C6 135.7(2) . . ? C4 Yb1 C6 164.1(3) . . ? C2 Yb1 C6 123.1(2) . . ? C1 Yb1 C6 133.0(3) . . ? C8 Yb1 C6 50.3(2) . . ? C9 Yb1 C6 49.7(2) . . ? C10 Yb1 C6 30.2(2) . . ? C11 N1 C15 119.1(4) . . ? C11 N1 Yb1 96.8(3) . . ? C15 N1 Yb1 143.8(3) . . ? C16 N2 C11 120.5(4) . . ? C16 N2 Yb1 135.6(3) . . ? C11 N2 Yb1 98.8(3) . . ? C23 N3 C16 126.2(4) . . ? C23 N3 C17 117.3(4) . . ? C16 N3 C17 116.4(4) . . ? C23 N4 C24 123.2(4) . . ? C23 N4 H4' 119(4) . . ? C24 N4 H4' 118(4) . . ? C23 O2 Yb1 138.9(3) . . ? C2 C1 C5 108.8(7) . . ? C2 C1 Yb1 75.1(4) . . ? C5 C1 Yb1 73.9(4) . . ? C2 C1 H1 125.6 . . ? C5 C1 H1 125.6 . . ? Yb1 C1 H1 117.3 . . ? C1 C2 C3 108.7(7) . . ? C1 C2 Yb1 75.4(4) . . ? C3 C2 Yb1 74.8(4) . . ? C1 C2 H2 125.7 . . ? C3 C2 H2 125.7 . . ? Yb1 C2 H2 116.2 . . ? C2 C3 C4 109.6(7) . . ? C2 C3 Yb1 75.3(4) . . ? C4 C3 Yb1 74.9(4) . . ? C2 C3 H3 125.2 . . ? C4 C3 H3 125.2 . . ? Yb1 C3 H3 116.5 . . ? C3 C4 C5 106.5(6) . . ? C3 C4 Yb1 74.7(3) . . ? C5 C4 Yb1 74.2(4) . . ? C3 C4 H4 126.8 . . ? C5 C4 H4 126.8 . . ? Yb1 C4 H4 116.6 . . ? C4 C5 C1 106.5(7) . . ? C4 C5 Yb1 74.8(3) . . ? C1 C5 Yb1 75.1(4) . . ? C4 C5 H5 126.7 . . ? C1 C5 H5 126.7 . . ? Yb1 C5 H5 115.7 . . ? C10 C6 C7 108.0(7) . . ? C10 C6 Yb1 74.3(3) . . ? C7 C6 Yb1 75.1(4) . . ? C10 C6 H6 126.0 . . ? C7 C6 H6 126.0 . . ? Yb1 C6 H6 116.6 . . ? C6 C7 C8 106.6(7) . . ? C6 C7 Yb1 74.5(4) . . ? C8 C7 Yb1 73.4(4) . . ? C6 C7 H7 126.7 . . ? C8 C7 H7 126.7 . . ? Yb1 C7 H7 117.5 . . ? C9 C8 C7 107.6(7) . . ? C9 C8 Yb1 75.0(3) . . ? C7 C8 Yb1 75.7(4) . . ? C9 C8 H8 126.2 . . ? C7 C8 H8 126.2 . . ? Yb1 C8 H8 115.3 . . ? C10 C9 C8 108.7(6) . . ? C10 C9 Yb1 75.3(3) . . ? C8 C9 Yb1 74.5(3) . . ? C10 C9 H9 125.6 . . ? C8 C9 H9 125.6 . . ? Yb1 C9 H9 116.5 . . ? C9 C10 C6 109.1(7) . . ? C9 C10 Yb1 75.1(3) . . ? C6 C10 Yb1 75.4(3) . . ? C9 C10 H10 125.4 . . ? C6 C10 H10 125.4 . . ? Yb1 C10 H10 116.0 . . ? N1 C11 N2 108.7(4) . . ? N1 C11 C12 121.5(4) . . ? N2 C11 C12 129.7(4) . . ? N1 C11 Yb1 55.8(2) . . ? N2 C11 Yb1 53.0(2) . . ? C12 C11 Yb1 173.3(3) . . ? C13 C12 C11 118.0(5) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? C12 C13 C14 120.7(5) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 118.2(5) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? N1 C15 C14 122.5(5) . . ? N1 C15 H15 118.7 . . ? C14 C15 H15 118.7 . . ? O1 C16 N2 128.2(4) . . ? O1 C16 N3 116.9(4) . . ? N2 C16 N3 114.9(4) . . ? C18 C17 C22 120.9(5) . . ? C18 C17 N3 118.8(5) . . ? C22 C17 N3 120.3(5) . . ? C17 C18 C19 119.3(6) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C20 C19 C18 120.5(7) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 120.6(6) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C20 C21 C22 120.4(6) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C17 C22 C21 118.4(6) . . ? C17 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? O2 C23 N4 119.7(4) . . ? O2 C23 N3 123.6(4) . . ? N4 C23 N3 116.8(4) . . ? C29 C24 C25 119.4(5) . . ? C29 C24 N4 121.9(5) . . ? C25 C24 N4 118.6(5) . . ? C26 C25 C24 120.5(6) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C27 120.0(6) . . ? C25 C26 H26 120.0 . . ? C27 C26 H26 120.0 . . ? C28 C27 C26 120.1(6) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C27 C28 C29 120.5(6) . . ? C27 C28 H28 119.7 . . ? C29 C28 H28 119.7 . . ? C24 C29 C28 119.5(6) . . ? C24 C29 H29 120.3 . . ? C28 C29 H29 120.3 . . ? C33 O3 C30 97.5(11) . . ? O3 C30 C31 119.2(13) . . ? O3 C30 H30A 107.5 . . ? C31 C30 H30A 107.5 . . ? O3 C30 H30B 107.5 . . ? C31 C30 H30B 107.5 . . ? H30A C30 H30B 107.0 . . ? C32 C31 C30 99.5(13) . . ? C32 C31 H31A 111.9 . . ? C30 C31 H31A 111.9 . . ? C32 C31 H31B 111.9 . . ? C30 C31 H31B 111.9 . . ? H31A C31 H31B 109.6 . . ? C31 C32 C33 98.5(12) . . ? C31 C32 H32A 112.1 . . ? C33 C32 H32A 112.1 . . ? C31 C32 H32B 112.1 . . ? C33 C32 H32B 112.1 . . ? H32A C32 H32B 109.7 . . ? O3 C33 C32 110.3(14) . . ? O3 C33 H33A 109.6 . . ? C32 C33 H33A 109.6 . . ? O3 C33 H33B 109.6 . . ? C32 C33 H33B 109.6 . . ? H33A C33 H33B 108.1 . . ? 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 Yb1 N1 C11 N2 -3.5(4) . . . . ? N1 C11 N2 C16 -154.9(4) . . . . ? C11 N2 C16 N3 -179.0(4) . . . . ? N2 C16 N3 C23 2.1(7) . . . . ? C16 N3 C23 O2 -14.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.702 _refine_diff_density_min -0.967 _refine_diff_density_rms 0.080 #======================================END data_f71225b _database_code_depnum_ccdc_archive 'CCDC 723135' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H33 N4 O3 Y' _chemical_formula_weight 622.54 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' Y Y -2.7962 3.5667 '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 9.795(16) _cell_length_b 11.88(2) _cell_length_c 26.18(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.61(3) _cell_angle_gamma 90.00 _cell_volume 3037(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2454 _cell_measurement_theta_min 2.285 _cell_measurement_theta_max 20.004 _exptl_crystal_description prism _exptl_crystal_colour lightred _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 1.959 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6953 _exptl_absorpt_correction_T_max 0.7989 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '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_% ? _diffrn_reflns_number 12541 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5342 _reflns_number_gt 3562 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0583P)^2^+1.4518P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5342 _refine_ls_number_parameters 373 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0879 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 0.981 _refine_ls_restrained_S_all 0.983 _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 Y1 Y 1.05639(4) 0.58334(3) 0.157697(15) 0.03732(15) Uani 1 1 d . . . N1 N 0.9404(3) 0.7422(3) 0.19608(13) 0.0478(9) Uani 1 1 d . . . N2 N 0.8188(3) 0.5918(3) 0.16903(14) 0.0432(8) Uani 1 1 d . . . N3 N 0.7213(3) 0.4395(3) 0.12142(14) 0.0430(9) Uani 1 1 d . . . N4 N 0.8284(4) 0.2688(3) 0.10973(17) 0.0568(11) Uani 1 1 d D . . H4' H 0.749(3) 0.244(4) 0.1024(18) 0.068 Uiso 1 1 d D . . O1 O 0.5913(3) 0.5901(3) 0.13915(14) 0.0613(9) Uani 1 1 d . . . O2 O 0.9559(3) 0.4153(2) 0.13655(12) 0.0517(8) Uani 1 1 d . . . C1 C 1.1074(10) 0.5670(6) 0.0604(2) 0.090(2) Uani 1 1 d . . . H1 H 1.1082 0.4947 0.0469 0.108 Uiso 1 1 calc R . . C2 C 1.2158(7) 0.6211(8) 0.0834(3) 0.090(2) Uani 1 1 d . . . H2 H 1.3041 0.5923 0.0887 0.108 Uiso 1 1 calc R . . C3 C 1.1750(8) 0.7251(6) 0.0976(2) 0.089(2) Uani 1 1 d . . . H3 H 1.2309 0.7794 0.1141 0.107 Uiso 1 1 calc R . . C4 C 1.0393(9) 0.7366(6) 0.0837(2) 0.0861(19) Uani 1 1 d . . . H4 H 0.9856 0.7996 0.0888 0.103 Uiso 1 1 calc R . . C5 C 0.9955(7) 0.6357(8) 0.0604(2) 0.088(2) Uani 1 1 d . . . H5 H 0.9069 0.6186 0.0473 0.106 Uiso 1 1 calc R . . C6 C 1.1341(6) 0.4681(8) 0.2430(3) 0.089(2) Uani 1 1 d . . . H6 H 1.0724 0.4156 0.2539 0.106 Uiso 1 1 calc R . . C7 C 1.1427(8) 0.5820(9) 0.2573(2) 0.106(3) Uani 1 1 d . . . H7 H 1.0878 0.6194 0.2792 0.127 Uiso 1 1 calc R . . C8 C 1.2489(8) 0.6277(6) 0.2322(3) 0.095(2) Uani 1 1 d . . . H8 H 1.2783 0.7021 0.2342 0.114 Uiso 1 1 calc R . . C9 C 1.3027(5) 0.5449(7) 0.2042(2) 0.0805(18) Uani 1 1 d . . . H9 H 1.3761 0.5534 0.1841 0.097 Uiso 1 1 calc R . . C10 C 1.2328(6) 0.4485(5) 0.2100(2) 0.0740(16) Uani 1 1 d . . . H10 H 1.2491 0.3802 0.1942 0.089 Uiso 1 1 calc R . . C11 C 0.8152(4) 0.6953(4) 0.19336(16) 0.0419(10) Uani 1 1 d . . . C12 C 0.7089(5) 0.7466(4) 0.21660(19) 0.0610(13) Uani 1 1 d . . . H12 H 0.6227 0.7135 0.2155 0.073 Uiso 1 1 calc R . . C13 C 0.7340(6) 0.8474(5) 0.2413(2) 0.0712(16) Uani 1 1 d . . . H13 H 0.6639 0.8826 0.2572 0.085 Uiso 1 1 calc R . . C14 C 0.8608(6) 0.8969(4) 0.2430(2) 0.0689(15) Uani 1 1 d . . . H14 H 0.8778 0.9657 0.2592 0.083 Uiso 1 1 calc R . . C15 C 0.9605(5) 0.8410(4) 0.22003(19) 0.0589(13) Uani 1 1 d . . . H15 H 1.0472 0.8732 0.2210 0.071 Uiso 1 1 calc R . . C16 C 0.7049(4) 0.5490(3) 0.14451(17) 0.0430(11) Uani 1 1 d . . . C17 C 0.6009(4) 0.3932(3) 0.09298(19) 0.0493(12) Uani 1 1 d . . . C18 C 0.5930(5) 0.3927(4) 0.0401(2) 0.0629(14) Uani 1 1 d . . . H18 H 0.6652 0.4211 0.0230 0.075 Uiso 1 1 calc R . . C19 C 0.4796(6) 0.3506(5) 0.0127(2) 0.0784(17) Uani 1 1 d . . . H19 H 0.4753 0.3494 -0.0229 0.094 Uiso 1 1 calc R . . C20 C 0.3733(6) 0.3106(5) 0.0376(3) 0.0828(19) Uani 1 1 d . . . H20 H 0.2961 0.2824 0.0188 0.099 Uiso 1 1 calc R . . C21 C 0.3788(5) 0.3114(5) 0.0893(3) 0.0807(19) Uani 1 1 d . . . H21 H 0.3047 0.2847 0.1058 0.097 Uiso 1 1 calc R . . C22 C 0.4941(5) 0.3518(4) 0.1184(2) 0.0642(14) Uani 1 1 d . . . H22 H 0.4985 0.3507 0.1540 0.077 Uiso 1 1 calc R . . C23 C 0.8415(5) 0.3766(4) 0.12304(17) 0.0434(11) Uani 1 1 d . . . C24 C 0.9420(4) 0.1980(4) 0.10124(19) 0.0467(11) Uani 1 1 d . . . C25 C 0.9746(5) 0.1806(5) 0.0521(2) 0.0660(14) Uani 1 1 d . . . H25 H 0.9272 0.2192 0.0253 0.079 Uiso 1 1 calc R . . C26 C 1.0757(6) 0.1076(5) 0.0419(3) 0.0821(18) Uani 1 1 d . . . H26 H 1.0963 0.0954 0.0083 0.099 Uiso 1 1 calc R . . C27 C 1.1460(6) 0.0527(5) 0.0808(3) 0.0790(18) Uani 1 1 d . . . H27 H 1.2145 0.0022 0.0738 0.095 Uiso 1 1 calc R . . C28 C 1.1179(6) 0.0702(5) 0.1302(3) 0.0854(19) Uani 1 1 d . . . H28 H 1.1677 0.0327 0.1567 0.102 Uiso 1 1 calc R . . C29 C 1.0142(5) 0.1449(5) 0.1409(2) 0.0686(15) Uani 1 1 d . . . H29 H 0.9945 0.1582 0.1745 0.082 Uiso 1 1 calc R . . O3 O 0.6432(6) 0.0803(4) 0.0906(3) 0.142(2) Uani 1 1 d D . . C30 C 0.6922(18) -0.0083(10) 0.0723(9) 0.47(2) Uani 1 1 d D . . H30A H 0.7899 -0.0079 0.0821 0.565 Uiso 1 1 calc R . . H30B H 0.6813 -0.0014 0.0353 0.565 Uiso 1 1 calc R . . C31 C 0.6439(13) -0.1135(8) 0.0844(5) 0.189(5) Uani 1 1 d D . . H31A H 0.6317 -0.1622 0.0547 0.227 Uiso 1 1 calc R . . H31B H 0.7022 -0.1501 0.1112 0.227 Uiso 1 1 calc R . . C32 C 0.5220(10) -0.0801(9) 0.1012(7) 0.266(10) Uani 1 1 d D . . H32A H 0.4941 -0.1275 0.1287 0.320 Uiso 1 1 calc R . . H32B H 0.4497 -0.0773 0.0737 0.320 Uiso 1 1 calc R . . C33 C 0.5627(17) 0.0309(10) 0.1192(6) 0.286(10) Uani 1 1 d D . . H33A H 0.4814 0.0767 0.1212 0.344 Uiso 1 1 calc R . . H33B H 0.6076 0.0247 0.1535 0.344 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 Y1 0.0326(2) 0.0431(2) 0.0362(2) -0.0017(2) 0.00239(15) -0.0008(2) N1 0.044(2) 0.053(2) 0.046(2) -0.0140(19) 0.0011(17) -0.0047(18) N2 0.0317(18) 0.049(2) 0.049(2) -0.0104(19) 0.0037(16) -0.0033(17) N3 0.0320(19) 0.041(2) 0.056(2) -0.0057(17) 0.0000(16) -0.0024(15) N4 0.040(2) 0.044(2) 0.087(3) -0.016(2) 0.002(2) -0.0066(18) O1 0.0355(18) 0.054(2) 0.093(3) -0.0154(19) -0.0023(16) 0.0075(15) O2 0.0340(16) 0.0431(17) 0.077(2) -0.0078(17) -0.0030(15) -0.0020(14) C1 0.145(7) 0.083(5) 0.045(3) -0.008(3) 0.027(4) 0.002(5) C2 0.071(4) 0.138(7) 0.066(4) 0.029(4) 0.031(4) 0.015(4) C3 0.112(6) 0.082(5) 0.075(4) 0.012(4) 0.022(4) -0.040(4) C4 0.121(6) 0.072(4) 0.069(4) 0.023(4) 0.031(4) 0.031(4) C5 0.078(4) 0.138(6) 0.046(4) 0.029(4) -0.008(3) -0.017(5) C6 0.056(4) 0.133(6) 0.074(4) 0.053(4) -0.013(3) -0.012(4) C7 0.093(5) 0.183(9) 0.038(3) -0.011(5) -0.016(3) 0.059(6) C8 0.100(5) 0.084(5) 0.090(5) -0.010(4) -0.056(5) -0.002(4) C9 0.039(3) 0.117(6) 0.083(4) 0.028(4) -0.008(3) 0.003(3) C10 0.067(4) 0.075(4) 0.077(4) 0.010(3) -0.016(3) 0.019(3) C11 0.040(2) 0.046(3) 0.040(2) -0.008(2) 0.002(2) 0.003(2) C12 0.048(3) 0.071(4) 0.065(3) -0.016(3) 0.009(2) 0.002(3) C13 0.063(4) 0.085(4) 0.066(4) -0.030(3) 0.007(3) 0.016(3) C14 0.070(4) 0.064(4) 0.071(4) -0.033(3) -0.004(3) 0.010(3) C15 0.054(3) 0.062(3) 0.060(3) -0.025(3) 0.003(3) -0.008(2) C16 0.037(3) 0.041(3) 0.051(3) -0.003(2) 0.008(2) -0.0002(19) C17 0.038(3) 0.040(3) 0.068(3) -0.008(2) -0.003(2) -0.0026(19) C18 0.063(3) 0.067(4) 0.056(3) 0.001(3) -0.009(3) -0.011(3) C19 0.082(4) 0.073(4) 0.075(4) -0.001(3) -0.025(3) -0.008(3) C20 0.063(4) 0.069(4) 0.112(6) -0.032(4) -0.027(4) -0.001(3) C21 0.041(3) 0.080(4) 0.122(6) -0.037(4) 0.012(3) -0.021(3) C22 0.052(3) 0.067(3) 0.074(4) -0.016(3) 0.008(3) -0.011(3) C23 0.048(3) 0.041(3) 0.042(3) 0.000(2) 0.006(2) 0.002(2) C24 0.044(3) 0.035(2) 0.060(3) -0.009(2) -0.001(2) -0.003(2) C25 0.066(3) 0.068(4) 0.065(4) 0.005(3) 0.005(3) 0.008(3) C26 0.080(4) 0.087(5) 0.081(4) -0.009(4) 0.023(4) 0.003(4) C27 0.060(4) 0.055(4) 0.123(6) -0.017(4) 0.017(4) 0.007(3) C28 0.075(4) 0.070(4) 0.105(5) 0.010(4) -0.030(4) 0.011(3) C29 0.071(4) 0.075(4) 0.058(3) 0.000(3) -0.008(3) 0.009(3) O3 0.119(4) 0.085(4) 0.225(7) -0.035(4) 0.041(4) -0.038(3) C30 0.55(3) 0.198(14) 0.74(4) -0.29(2) 0.50(3) -0.256(19) C31 0.187(11) 0.117(8) 0.258(15) -0.010(8) -0.022(11) 0.025(8) C32 0.084(7) 0.115(8) 0.60(3) 0.041(13) 0.018(12) -0.011(6) C33 0.39(2) 0.162(12) 0.34(2) -0.069(13) 0.226(18) -0.109(14) _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 Y1 O2 2.275(4) . ? Y1 N2 2.372(5) . ? Y1 N1 2.459(4) . ? Y1 C2 2.629(6) . ? Y1 C3 2.638(6) . ? Y1 C1 2.640(7) . ? Y1 C5 2.643(7) . ? Y1 C9 2.653(6) . ? Y1 C4 2.654(6) . ? Y1 C8 2.655(6) . ? Y1 C10 2.655(6) . ? Y1 C7 2.675(7) . ? N1 C15 1.338(6) . ? N1 C11 1.344(5) . ? N2 C16 1.342(5) . ? N2 C11 1.386(5) . ? N3 C23 1.392(6) . ? N3 C16 1.449(5) . ? N3 C17 1.451(6) . ? N4 C23 1.331(6) . ? N4 C24 1.427(6) . ? N4 H4' 0.836(19) . ? O1 C16 1.213(5) . ? O2 C23 1.236(5) . ? C1 C2 1.341(9) . ? C1 C5 1.367(9) . ? C1 H1 0.9300 . ? C2 C3 1.360(9) . ? C2 H2 0.9300 . ? C3 C4 1.357(8) . ? C3 H3 0.9300 . ? C4 C5 1.396(9) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C10 1.367(9) . ? C6 C7 1.405(10) . ? C6 H6 0.9300 . ? C7 C8 1.385(10) . ? C7 H7 0.9300 . ? C8 C9 1.359(9) . ? C8 H8 0.9300 . ? C9 C10 1.350(8) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.388(6) . ? C12 C13 1.374(7) . ? C12 H12 0.9300 . ? C13 C14 1.371(7) . ? C13 H13 0.9300 . ? C14 C15 1.361(7) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C22 1.375(6) . ? C17 C18 1.379(7) . ? C18 C19 1.368(7) . ? C18 H18 0.9300 . ? C19 C20 1.357(8) . ? C19 H19 0.9300 . ? C20 C21 1.351(9) . ? C20 H20 0.9300 . ? C21 C22 1.395(7) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C24 C29 1.363(7) . ? C24 C25 1.367(7) . ? C25 C26 1.359(7) . ? C25 H25 0.9300 . ? C26 C27 1.352(9) . ? C26 H26 0.9300 . ? C27 C28 1.358(9) . ? C27 H27 0.9300 . ? C28 C29 1.394(8) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? O3 C30 1.267(8) . ? O3 C33 1.273(8) . ? C30 C31 1.382(12) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.364(12) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.445(13) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Y1 N2 70.01(12) . . ? O2 Y1 N1 124.63(15) . . ? N2 Y1 N1 54.98(12) . . ? O2 Y1 C2 103.9(2) . . ? N2 Y1 C2 137.09(18) . . ? N1 Y1 C2 119.5(2) . . ? O2 Y1 C3 128.18(19) . . ? N2 Y1 C3 122.1(2) . . ? N1 Y1 C3 89.6(2) . . ? C2 Y1 C3 29.9(2) . . ? O2 Y1 C1 79.20(18) . . ? N2 Y1 C1 112.8(2) . . ? N1 Y1 C1 125.43(19) . . ? C2 Y1 C1 29.5(2) . . ? C3 Y1 C1 49.1(2) . . ? O2 Y1 C5 85.0(2) . . ? N2 Y1 C5 87.87(18) . . ? N1 Y1 C5 97.9(2) . . ? C2 Y1 C5 49.3(2) . . ? C3 Y1 C5 49.5(2) . . ? C1 Y1 C5 30.0(2) . . ? O2 Y1 C9 108.7(2) . . ? N2 Y1 C9 144.60(18) . . ? N1 Y1 C9 112.2(2) . . ? C2 Y1 C9 78.3(2) . . ? C3 Y1 C9 87.5(2) . . ? C1 Y1 C9 101.2(3) . . ? C5 Y1 C9 127.5(2) . . ? O2 Y1 C4 115.1(2) . . ? N2 Y1 C4 93.26(19) . . ? N1 Y1 C4 76.54(19) . . ? C2 Y1 C4 49.4(2) . . ? C3 Y1 C4 29.71(19) . . ? C1 Y1 C4 49.7(2) . . ? C5 Y1 C4 30.6(2) . . ? C9 Y1 C4 117.0(2) . . ? O2 Y1 C8 128.39(18) . . ? N2 Y1 C8 123.1(3) . . ? N1 Y1 C8 82.6(2) . . ? C2 Y1 C8 94.6(3) . . ? C3 Y1 C8 89.5(3) . . ? C1 Y1 C8 123.0(3) . . ? C5 Y1 C8 138.9(3) . . ? C9 Y1 C8 29.7(2) . . ? C4 Y1 C8 113.5(3) . . ? O2 Y1 C10 81.17(19) . . ? N2 Y1 C10 124.45(19) . . ? N1 Y1 C10 123.75(19) . . ? C2 Y1 C10 94.8(2) . . ? C3 Y1 C10 113.2(3) . . ? C1 Y1 C10 106.7(2) . . ? C5 Y1 C10 136.6(2) . . ? C9 Y1 C10 29.47(17) . . ? C4 Y1 C10 142.3(2) . . ? C8 Y1 C10 49.2(2) . . ? O2 Y1 C7 109.2(3) . . ? N2 Y1 C7 96.6(2) . . ? N1 Y1 C7 74.1(2) . . ? C2 Y1 C7 124.2(3) . . ? C3 Y1 C7 117.7(3) . . ? C1 Y1 C7 150.4(3) . . ? C5 Y1 C7 165.8(3) . . ? C9 Y1 C7 49.3(2) . . ? C4 Y1 C7 135.4(3) . . ? C8 Y1 C7 30.1(2) . . ? C10 Y1 C7 49.6(2) . . ? C15 N1 C11 119.2(4) . . ? C15 N1 Y1 144.1(3) . . ? C11 N1 Y1 96.3(3) . . ? C16 N2 C11 120.4(3) . . ? C16 N2 Y1 135.2(3) . . ? C11 N2 Y1 99.0(2) . . ? C23 N3 C16 126.2(4) . . ? C23 N3 C17 117.6(4) . . ? C16 N3 C17 116.2(3) . . ? C23 N4 C24 123.3(4) . . ? C23 N4 H4' 118(3) . . ? C24 N4 H4' 119(3) . . ? C23 O2 Y1 139.5(3) . . ? C2 C1 C5 108.7(7) . . ? C2 C1 Y1 74.8(3) . . ? C5 C1 Y1 75.1(3) . . ? C2 C1 H1 125.7 . . ? C5 C1 H1 125.7 . . ? Y1 C1 H1 116.4 . . ? C1 C2 C3 108.6(6) . . ? C1 C2 Y1 75.7(3) . . ? C3 C2 Y1 75.4(3) . . ? C1 C2 H2 125.7 . . ? C3 C2 H2 125.7 . . ? Y1 C2 H2 115.3 . . ? C4 C3 C2 108.7(6) . . ? C4 C3 Y1 75.8(3) . . ? C2 C3 Y1 74.7(4) . . ? C4 C3 H3 125.6 . . ? C2 C3 H3 125.6 . . ? Y1 C3 H3 115.9 . . ? C3 C4 C5 106.9(6) . . ? C3 C4 Y1 74.5(3) . . ? C5 C4 Y1 74.3(3) . . ? C3 C4 H4 126.6 . . ? C5 C4 H4 126.6 . . ? Y1 C4 H4 116.9 . . ? C1 C5 C4 107.1(6) . . ? C1 C5 Y1 74.9(3) . . ? C4 C5 Y1 75.1(3) . . ? C1 C5 H5 126.4 . . ? C4 C5 H5 126.4 . . ? Y1 C5 H5 115.8 . . ? C10 C6 C7 107.6(6) . . ? C10 C6 Y1 74.3(3) . . ? C7 C6 Y1 74.7(3) . . ? C10 C6 H6 126.2 . . ? C7 C6 H6 126.2 . . ? Y1 C6 H6 116.9 . . ? C8 C7 C6 106.4(6) . . ? C8 C7 Y1 74.1(4) . . ? C6 C7 Y1 74.8(3) . . ? C8 C7 H7 126.8 . . ? C6 C7 H7 126.8 . . ? Y1 C7 H7 116.5 . . ? C9 C8 C7 108.1(7) . . ? C9 C8 Y1 75.1(3) . . ? C7 C8 Y1 75.7(4) . . ? C9 C8 H8 126.0 . . ? C7 C8 H8 126.0 . . ? Y1 C8 H8 115.4 . . ? C10 C9 C8 109.4(6) . . ? C10 C9 Y1 75.4(3) . . ? C8 C9 Y1 75.2(3) . . ? C10 C9 H9 125.3 . . ? C8 C9 H9 125.3 . . ? Y1 C9 H9 116.0 . . ? C9 C10 C6 108.5(6) . . ? C9 C10 Y1 75.2(3) . . ? C6 C10 Y1 76.0(3) . . ? C9 C10 H10 125.8 . . ? C6 C10 H10 125.8 . . ? Y1 C10 H10 115.2 . . ? N1 C11 N2 109.6(3) . . ? N1 C11 C12 120.5(4) . . ? N2 C11 C12 129.7(4) . . ? N1 C11 Y1 56.6(2) . . ? N2 C11 Y1 53.12(19) . . ? C12 C11 Y1 172.6(3) . . ? C13 C12 C11 118.5(5) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C14 C13 C12 121.1(5) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C13 117.1(5) . . ? C15 C14 H14 121.4 . . ? C13 C14 H14 121.4 . . ? N1 C15 C14 123.5(5) . . ? N1 C15 H15 118.3 . . ? C14 C15 H15 118.2 . . ? O1 C16 N2 128.5(4) . . ? O1 C16 N3 116.4(4) . . ? N2 C16 N3 115.1(4) . . ? C22 C17 C18 120.0(5) . . ? C22 C17 N3 120.4(5) . . ? C18 C17 N3 119.6(4) . . ? C19 C18 C17 120.4(5) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C20 C19 C18 119.9(6) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.1 . . ? C21 C20 C19 120.5(6) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 121.0(5) . . ? C20 C21 H21 119.5 . . ? C22 C21 H21 119.5 . . ? C17 C22 C21 118.3(5) . . ? C17 C22 H22 120.9 . . ? C21 C22 H22 120.9 . . ? O2 C23 N4 119.9(4) . . ? O2 C23 N3 123.7(4) . . ? N4 C23 N3 116.4(4) . . ? C29 C24 C25 120.1(5) . . ? C29 C24 N4 121.2(5) . . ? C25 C24 N4 118.7(4) . . ? C26 C25 C24 120.7(5) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C27 C26 C25 119.7(6) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C26 C27 C28 120.9(6) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C27 C28 C29 119.7(6) . . ? C27 C28 H28 120.1 . . ? C29 C28 H28 120.1 . . ? C24 C29 C28 118.9(5) . . ? C24 C29 H29 120.5 . . ? C28 C29 H29 120.5 . . ? C30 O3 C33 96.3(9) . . ? O3 C30 C31 121.2(10) . . ? O3 C30 H30A 107.0 . . ? C31 C30 H30A 107.0 . . ? O3 C30 H30B 107.0 . . ? C31 C30 H30B 107.0 . . ? H30A C30 H30B 106.8 . . ? C32 C31 C30 97.8(9) . . ? C32 C31 H31A 112.2 . . ? C30 C31 H31A 112.2 . . ? C32 C31 H31B 112.2 . . ? C30 C31 H31B 112.2 . . ? H31A C31 H31B 109.8 . . ? C31 C32 C33 98.3(10) . . ? C31 C32 H32A 112.1 . . ? C33 C32 H32A 112.1 . . ? C31 C32 H32B 112.1 . . ? C33 C32 H32B 112.1 . . ? H32A C32 H32B 109.7 . . ? O3 C33 C32 113.5(11) . . ? O3 C33 H33A 108.9 . . ? C32 C33 H33A 108.9 . . ? O3 C33 H33B 108.9 . . ? C32 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4' O3 0.836(19) 2.22(4) 2.901(7) 139(4) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.603 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.068 #======================================END data_f80110b _database_code_depnum_ccdc_archive 'CCDC 723136' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H33 Dy N4 O3' _chemical_formula_weight 696.13 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' Dy Dy -0.1892 4.4098 '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 9.821(4) _cell_length_b 11.862(4) _cell_length_c 26.143(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.762(5) _cell_angle_gamma 90.00 _cell_volume 3035.2(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7937 _cell_measurement_theta_min 2.283 _cell_measurement_theta_max 27.038 _exptl_crystal_description prism _exptl_crystal_colour light-yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1396 _exptl_absorpt_coefficient_mu 2.501 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6347 _exptl_absorpt_correction_T_max 0.7881 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '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_% ? _diffrn_reflns_number 14735 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5331 _reflns_number_gt 4607 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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. ; _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5331 _refine_ls_number_parameters 373 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.1299 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.090 _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 Dy1 Dy 1.05678(2) 0.58378(2) 0.157807(9) 0.03513(14) Uani 1 1 d . . . N1 N 0.9389(5) 0.7416(4) 0.1963(2) 0.0458(11) Uani 1 1 d . . . N2 N 0.8174(5) 0.5917(4) 0.1687(2) 0.0421(11) Uani 1 1 d . . . N3 N 0.7209(5) 0.4397(4) 0.1213(2) 0.0414(11) Uani 1 1 d . . . N4 N 0.8277(5) 0.2693(4) 0.1098(2) 0.0529(13) Uani 1 1 d D . . H4' H 0.745(3) 0.254(6) 0.099(3) 0.063 Uiso 1 1 d D . . O1 O 0.5908(5) 0.5900(3) 0.1388(2) 0.0610(13) Uani 1 1 d . . . O2 O 0.9546(5) 0.4144(3) 0.1368(2) 0.0535(12) Uani 1 1 d . . . C1 C 1.1091(13) 0.5660(8) 0.0606(3) 0.084(3) Uani 1 1 d . . . H1 H 1.1102 0.4930 0.0477 0.101 Uiso 1 1 calc R . . C2 C 1.2173(11) 0.6201(10) 0.0826(4) 0.091(3) Uani 1 1 d . . . H2 H 1.3057 0.5918 0.0875 0.110 Uiso 1 1 calc R . . C3 C 1.1762(12) 0.7231(8) 0.0964(3) 0.086(3) Uani 1 1 d . . . H3 H 1.2330 0.7779 0.1122 0.103 Uiso 1 1 calc R . . C4 C 1.0388(11) 0.7356(7) 0.0839(3) 0.081(3) Uani 1 1 d . . . H4 H 0.9858 0.7984 0.0901 0.097 Uiso 1 1 calc R . . C5 C 0.9938(11) 0.6349(11) 0.0600(3) 0.089(3) Uani 1 1 d . . . H5 H 0.9056 0.6177 0.0465 0.107 Uiso 1 1 calc R . . C6 C 1.1344(8) 0.4725(11) 0.2441(4) 0.086(3) Uani 1 1 d . . . H6 H 1.0709 0.4217 0.2552 0.104 Uiso 1 1 calc R . . C7 C 1.1467(13) 0.5849(12) 0.2579(4) 0.102(5) Uani 1 1 d . . . H7 H 1.0945 0.6234 0.2803 0.123 Uiso 1 1 calc R . . C8 C 1.2508(11) 0.6288(8) 0.2321(4) 0.087(3) Uani 1 1 d . . . H8 H 1.2804 0.7033 0.2334 0.104 Uiso 1 1 calc R . . C9 C 1.3040(7) 0.5433(8) 0.2039(3) 0.075(2) Uani 1 1 d . . . H9 H 1.3768 0.5506 0.1835 0.090 Uiso 1 1 calc R . . C10 C 1.2345(8) 0.4489(7) 0.2106(4) 0.072(2) Uani 1 1 d . . . H10 H 1.2498 0.3794 0.1956 0.087 Uiso 1 1 calc R . . C11 C 0.8144(6) 0.6946(5) 0.1933(2) 0.0398(12) Uani 1 1 d . . . C12 C 0.7055(7) 0.7450(6) 0.2169(3) 0.0628(18) Uani 1 1 d . . . H12 H 0.6202 0.7106 0.2160 0.075 Uiso 1 1 calc R . . C13 C 0.7298(7) 0.8472(6) 0.2415(3) 0.065(2) Uani 1 1 d . . . H13 H 0.6596 0.8829 0.2570 0.078 Uiso 1 1 calc R . . C14 C 0.8578(8) 0.8967(6) 0.2432(3) 0.0627(19) Uani 1 1 d . . . H14 H 0.8743 0.9651 0.2600 0.075 Uiso 1 1 calc R . . C15 C 0.9600(7) 0.8434(5) 0.2198(3) 0.0538(16) Uani 1 1 d . . . H15 H 1.0453 0.8775 0.2199 0.065 Uiso 1 1 calc R . . C16 C 0.7041(5) 0.5494(5) 0.1446(2) 0.0381(12) Uani 1 1 d . . . C17 C 0.5999(6) 0.3927(4) 0.0931(3) 0.0430(14) Uani 1 1 d . . . C18 C 0.5932(8) 0.3914(6) 0.0396(3) 0.0614(18) Uani 1 1 d . . . H18 H 0.6651 0.4190 0.0222 0.074 Uiso 1 1 calc R . . C19 C 0.4777(9) 0.3484(6) 0.0131(3) 0.074(2) Uani 1 1 d . . . H19 H 0.4731 0.3455 -0.0226 0.089 Uiso 1 1 calc R . . C20 C 0.3729(9) 0.3110(7) 0.0372(4) 0.076(2) Uani 1 1 d . . . H20 H 0.2958 0.2838 0.0181 0.091 Uiso 1 1 calc R . . C21 C 0.3761(8) 0.3116(7) 0.0893(4) 0.075(2) Uani 1 1 d . . . H21 H 0.3015 0.2855 0.1056 0.091 Uiso 1 1 calc R . . C22 C 0.4938(6) 0.3522(6) 0.1187(3) 0.0582(17) Uani 1 1 d . . . H22 H 0.4989 0.3514 0.1543 0.070 Uiso 1 1 calc R . . C23 C 0.8392(6) 0.3753(5) 0.1232(2) 0.0382(12) Uani 1 1 d . . . C24 C 0.9396(6) 0.1984(5) 0.1017(3) 0.0458(14) Uani 1 1 d . . . C25 C 0.9725(8) 0.1807(6) 0.0519(3) 0.0657(19) Uani 1 1 d . . . H25 H 0.9241 0.2181 0.0249 0.079 Uiso 1 1 calc R . . C26 C 1.0770(9) 0.1078(7) 0.0421(4) 0.078(2) Uani 1 1 d . . . H26 H 1.0992 0.0965 0.0085 0.094 Uiso 1 1 calc R . . C27 C 1.1477(8) 0.0524(6) 0.0817(4) 0.075(3) Uani 1 1 d . . . H27 H 1.2175 0.0030 0.0749 0.090 Uiso 1 1 calc R . . C28 C 1.1171(9) 0.0688(6) 0.1304(4) 0.078(3) Uani 1 1 d . . . H28 H 1.1653 0.0299 0.1570 0.094 Uiso 1 1 calc R . . C29 C 1.0129(8) 0.1442(6) 0.1417(3) 0.0619(18) Uani 1 1 d . . . H29 H 0.9940 0.1571 0.1755 0.074 Uiso 1 1 calc R . . O3 O 0.6438(10) 0.0783(6) 0.0897(5) 0.136(4) Uani 1 1 d . . . C30 C 0.715(2) -0.0240(18) 0.0809(14) 0.33(2) Uani 1 1 d . . . H30A H 0.7611 -0.0175 0.0496 0.401 Uiso 1 1 calc R . . H30B H 0.7836 -0.0376 0.1091 0.401 Uiso 1 1 calc R . . C31 C 0.628(3) -0.1096(15) 0.0768(9) 0.250(14) Uani 1 1 d . . . H31A H 0.6726 -0.1791 0.0881 0.301 Uiso 1 1 calc R . . H31B H 0.5906 -0.1187 0.0415 0.301 Uiso 1 1 calc R . . C32 C 0.5259(17) -0.0835(15) 0.1075(9) 0.190(10) Uani 1 1 d . . . H32A H 0.5287 -0.1303 0.1380 0.228 Uiso 1 1 calc R . . H32B H 0.4359 -0.0872 0.0892 0.228 Uiso 1 1 calc R . . C33 C 0.569(4) 0.0336(16) 0.1192(11) 0.32(2) Uani 1 1 d . . . H33A H 0.4880 0.0796 0.1203 0.382 Uiso 1 1 calc R . . H33B H 0.6165 0.0346 0.1533 0.382 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 Dy1 0.03067(19) 0.03683(19) 0.0381(2) -0.00165(10) 0.00396(12) -0.00082(9) N1 0.043(3) 0.044(3) 0.050(3) -0.019(2) 0.003(2) 0.000(2) N2 0.034(3) 0.041(3) 0.052(3) -0.011(2) 0.008(2) -0.0053(19) N3 0.037(3) 0.033(2) 0.054(3) -0.008(2) 0.001(2) -0.0049(19) N4 0.038(3) 0.035(3) 0.085(4) -0.015(2) 0.001(3) 0.000(2) O1 0.035(2) 0.049(3) 0.097(4) -0.020(2) -0.003(2) 0.0053(18) O2 0.039(2) 0.038(2) 0.083(4) -0.008(2) 0.002(2) -0.0008(17) C1 0.128(9) 0.081(6) 0.046(5) -0.004(4) 0.028(5) 0.004(6) C2 0.080(6) 0.120(8) 0.081(6) 0.028(6) 0.047(5) 0.022(6) C3 0.123(9) 0.065(5) 0.072(6) 0.010(4) 0.029(6) -0.041(6) C4 0.110(7) 0.068(5) 0.069(5) 0.026(4) 0.027(5) 0.031(5) C5 0.087(7) 0.136(9) 0.041(4) 0.024(5) -0.012(4) -0.023(6) C6 0.053(5) 0.131(8) 0.073(6) 0.053(6) -0.009(4) -0.019(5) C7 0.094(8) 0.168(13) 0.041(5) -0.013(6) -0.015(5) 0.063(8) C8 0.088(7) 0.073(5) 0.091(7) -0.007(5) -0.045(6) -0.008(5) C9 0.036(4) 0.101(6) 0.086(6) 0.026(5) -0.004(4) 0.003(4) C10 0.058(5) 0.067(4) 0.087(6) 0.019(4) -0.014(4) 0.011(4) C11 0.037(3) 0.044(3) 0.038(3) -0.004(2) 0.005(2) -0.001(2) C12 0.050(4) 0.071(4) 0.068(4) -0.029(4) 0.010(3) 0.003(3) C13 0.058(4) 0.067(5) 0.071(5) -0.024(4) 0.009(4) 0.020(4) C14 0.072(5) 0.049(4) 0.067(5) -0.029(3) 0.001(4) 0.007(3) C15 0.055(4) 0.051(4) 0.056(4) -0.019(3) 0.002(3) -0.009(3) C16 0.029(3) 0.035(3) 0.052(3) -0.003(2) 0.009(2) -0.004(2) C17 0.032(3) 0.029(3) 0.067(4) -0.009(3) -0.003(3) -0.005(2) C18 0.067(5) 0.053(4) 0.064(5) 0.005(3) 0.001(4) -0.011(3) C19 0.082(6) 0.059(4) 0.078(5) -0.006(4) -0.022(4) -0.013(4) C20 0.060(5) 0.071(5) 0.091(7) -0.020(5) -0.027(4) -0.002(4) C21 0.047(4) 0.069(5) 0.111(7) -0.021(5) 0.007(4) -0.013(4) C22 0.041(3) 0.064(4) 0.071(5) -0.015(4) 0.014(3) -0.010(3) C23 0.035(3) 0.036(3) 0.044(3) -0.001(2) 0.005(2) -0.001(2) C24 0.041(3) 0.027(3) 0.068(4) -0.007(3) 0.004(3) -0.005(2) C25 0.074(5) 0.063(4) 0.062(5) 0.005(4) 0.013(4) 0.003(4) C26 0.081(6) 0.069(5) 0.090(6) -0.008(5) 0.030(5) 0.010(4) C27 0.057(4) 0.043(4) 0.126(8) -0.017(5) 0.020(5) 0.001(3) C28 0.065(5) 0.060(5) 0.104(7) 0.010(4) -0.024(5) 0.022(4) C29 0.068(4) 0.067(5) 0.049(4) -0.002(3) -0.005(3) 0.006(4) O3 0.099(6) 0.079(5) 0.232(13) 0.001(5) 0.033(7) -0.015(4) C30 0.173(17) 0.159(16) 0.70(6) -0.19(3) 0.25(3) -0.089(15) C31 0.33(3) 0.161(14) 0.29(3) -0.124(17) 0.17(2) -0.170(18) C32 0.100(11) 0.22(2) 0.25(2) 0.106(16) 0.025(13) -0.026(11) C33 0.53(5) 0.118(13) 0.35(4) -0.083(18) 0.27(4) -0.13(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 Dy1 O2 2.292(4) . ? Dy1 N2 2.393(5) . ? Dy1 N1 2.461(5) . ? Dy1 C4 2.637(7) . ? Dy1 C1 2.642(8) . ? Dy1 C3 2.645(8) . ? Dy1 C5 2.651(8) . ? Dy1 C2 2.656(8) . ? Dy1 C8 2.660(8) . ? Dy1 C9 2.663(7) . ? Dy1 C10 2.666(7) . ? Dy1 C6 2.670(8) . ? N1 C11 1.340(7) . ? N1 C15 1.362(7) . ? N2 C16 1.331(7) . ? N2 C11 1.381(7) . ? N3 C23 1.388(8) . ? N3 C16 1.452(7) . ? N3 C17 1.457(7) . ? N4 C23 1.307(7) . ? N4 C24 1.414(7) . ? N4 H4' 0.85(2) . ? O1 C16 1.211(7) . ? O2 C23 1.249(7) . ? C1 C2 1.329(15) . ? C1 C5 1.396(15) . ? C1 H1 0.9300 . ? C2 C3 1.346(13) . ? C2 H2 0.9300 . ? C3 C4 1.370(13) . ? C3 H3 0.9300 . ? C4 C5 1.402(14) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.384(14) . ? C6 C10 1.399(14) . ? C6 H6 0.9300 . ? C7 C8 1.374(16) . ? C7 H7 0.9300 . ? C8 C9 1.381(14) . ? C8 H8 0.9300 . ? C9 C10 1.331(11) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.411(8) . ? C12 C13 1.383(9) . ? C12 H12 0.9300 . ? C13 C14 1.385(10) . ? C13 H13 0.9300 . ? C14 C15 1.373(10) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C22 1.369(9) . ? C17 C18 1.396(10) . ? C18 C19 1.377(11) . ? C18 H18 0.9300 . ? C19 C20 1.328(12) . ? C19 H19 0.9300 . ? C20 C21 1.359(12) . ? C20 H20 0.9300 . ? C21 C22 1.418(10) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C24 C29 1.378(10) . ? C24 C25 1.384(9) . ? C25 C26 1.383(11) . ? C25 H25 0.9300 . ? C26 C27 1.366(13) . ? C26 H26 0.9300 . ? C27 C28 1.348(13) . ? C27 H27 0.9300 . ? C28 C29 1.407(11) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? O3 C33 1.23(2) . ? O3 C30 1.43(2) . ? C30 C31 1.329(19) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.37(2) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.48(2) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Dy1 N2 69.40(15) . . ? O2 Dy1 N1 123.61(16) . . ? N2 Dy1 N1 54.62(15) . . ? O2 Dy1 C4 115.0(3) . . ? N2 Dy1 C4 93.1(3) . . ? N1 Dy1 C4 77.0(2) . . ? O2 Dy1 C1 79.4(3) . . ? N2 Dy1 C1 112.9(3) . . ? N1 Dy1 C1 126.2(3) . . ? C4 Dy1 C1 49.9(3) . . ? O2 Dy1 C3 127.6(2) . . ? N2 Dy1 C3 122.5(3) . . ? N1 Dy1 C3 91.2(3) . . ? C4 Dy1 C3 30.1(3) . . ? C1 Dy1 C3 48.3(3) . . ? O2 Dy1 C5 84.7(3) . . ? N2 Dy1 C5 87.3(3) . . ? N1 Dy1 C5 98.1(3) . . ? C4 Dy1 C5 30.8(3) . . ? C1 Dy1 C5 30.6(3) . . ? C3 Dy1 C5 49.6(3) . . ? O2 Dy1 C2 103.9(3) . . ? N2 Dy1 C2 137.0(3) . . ? N1 Dy1 C2 120.5(3) . . ? C4 Dy1 C2 49.8(3) . . ? C1 Dy1 C2 29.1(3) . . ? C3 Dy1 C2 29.4(3) . . ? C5 Dy1 C2 49.7(3) . . ? O2 Dy1 C8 128.6(2) . . ? N2 Dy1 C8 123.8(3) . . ? N1 Dy1 C8 83.2(3) . . ? C4 Dy1 C8 113.5(3) . . ? C1 Dy1 C8 122.2(4) . . ? C3 Dy1 C8 89.5(3) . . ? C5 Dy1 C8 138.9(3) . . ? C2 Dy1 C8 94.3(4) . . ? O2 Dy1 C9 108.3(2) . . ? N2 Dy1 C9 145.2(2) . . ? N1 Dy1 C9 113.2(2) . . ? C4 Dy1 C9 117.2(3) . . ? C1 Dy1 C9 100.2(3) . . ? C3 Dy1 C9 87.3(3) . . ? C5 Dy1 C9 127.5(3) . . ? C2 Dy1 C9 77.9(3) . . ? C8 Dy1 C9 30.1(3) . . ? O2 Dy1 C10 81.5(2) . . ? N2 Dy1 C10 124.7(2) . . ? N1 Dy1 C10 123.7(3) . . ? C4 Dy1 C10 142.2(3) . . ? C1 Dy1 C10 106.2(3) . . ? C3 Dy1 C10 112.6(3) . . ? C5 Dy1 C10 136.6(4) . . ? C2 Dy1 C10 94.4(3) . . ? C8 Dy1 C10 49.0(3) . . ? C9 Dy1 C10 28.9(2) . . ? O2 Dy1 C6 81.8(3) . . ? N2 Dy1 C6 97.6(2) . . ? N1 Dy1 C6 98.1(3) . . ? C4 Dy1 C6 162.6(3) . . ? C1 Dy1 C6 135.1(4) . . ? C3 Dy1 C6 135.4(3) . . ? C5 Dy1 C6 162.9(4) . . ? C2 Dy1 C6 124.1(3) . . ? C8 Dy1 C6 49.1(3) . . ? C9 Dy1 C6 48.9(3) . . ? C10 Dy1 C6 30.4(3) . . ? C11 N1 C15 120.0(5) . . ? C11 N1 Dy1 96.7(3) . . ? C15 N1 Dy1 143.1(4) . . ? C16 N2 C11 120.3(5) . . ? C16 N2 Dy1 136.0(4) . . ? C11 N2 Dy1 98.6(3) . . ? C23 N3 C16 127.0(5) . . ? C23 N3 C17 116.9(5) . . ? C16 N3 C17 116.0(5) . . ? C23 N4 C24 124.2(5) . . ? C23 N4 H4' 111(5) . . ? C24 N4 H4' 124(5) . . ? C23 O2 Dy1 139.7(4) . . ? C2 C1 C5 109.9(9) . . ? C2 C1 Dy1 76.1(5) . . ? C5 C1 Dy1 75.1(5) . . ? C2 C1 H1 125.0 . . ? C5 C1 H1 125.0 . . ? Dy1 C1 H1 115.7 . . ? C1 C2 C3 108.0(10) . . ? C1 C2 Dy1 74.9(5) . . ? C3 C2 Dy1 74.9(5) . . ? C1 C2 H2 126.0 . . ? C3 C2 H2 126.0 . . ? Dy1 C2 H2 116.4 . . ? C2 C3 C4 110.2(9) . . ? C2 C3 Dy1 75.7(5) . . ? C4 C3 Dy1 74.6(5) . . ? C2 C3 H3 124.9 . . ? C4 C3 H3 124.9 . . ? Dy1 C3 H3 116.6 . . ? C3 C4 C5 106.4(8) . . ? C3 C4 Dy1 75.3(5) . . ? C5 C4 Dy1 75.2(5) . . ? C3 C4 H4 126.8 . . ? C5 C4 H4 126.8 . . ? Dy1 C4 H4 115.1 . . ? C1 C5 C4 105.6(9) . . ? C1 C5 Dy1 74.4(5) . . ? C4 C5 Dy1 74.1(4) . . ? C1 C5 H5 127.2 . . ? C4 C5 H5 127.2 . . ? Dy1 C5 H5 116.7 . . ? C7 C6 C10 107.8(9) . . ? C7 C6 Dy1 75.9(5) . . ? C10 C6 Dy1 74.6(4) . . ? C7 C6 H6 126.1 . . ? C10 C6 H6 126.1 . . ? Dy1 C6 H6 115.6 . . ? C8 C7 C6 106.8(9) . . ? C8 C7 Dy1 73.8(5) . . ? C6 C7 Dy1 74.2(5) . . ? C8 C7 H7 126.6 . . ? C6 C7 H7 126.6 . . ? Dy1 C7 H7 117.5 . . ? C7 C8 C9 108.3(9) . . ? C7 C8 Dy1 76.4(5) . . ? C9 C8 Dy1 75.1(4) . . ? C7 C8 H8 125.8 . . ? C9 C8 H8 125.8 . . ? Dy1 C8 H8 114.8 . . ? C10 C9 C8 109.1(8) . . ? C10 C9 Dy1 75.7(4) . . ? C8 C9 Dy1 74.8(4) . . ? C10 C9 H9 125.5 . . ? C8 C9 H9 125.5 . . ? Dy1 C9 H9 116.0 . . ? C9 C10 C6 108.0(9) . . ? C9 C10 Dy1 75.4(4) . . ? C6 C10 Dy1 75.0(5) . . ? C9 C10 H10 126.0 . . ? C6 C10 H10 126.0 . . ? Dy1 C10 H10 115.8 . . ? N1 C11 N2 109.9(5) . . ? N1 C11 C12 121.3(5) . . ? N2 C11 C12 128.7(5) . . ? N1 C11 Dy1 56.3(3) . . ? N2 C11 Dy1 53.7(3) . . ? C12 C11 Dy1 172.6(5) . . ? C13 C12 C11 117.8(6) . . ? C13 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C12 C13 C14 120.6(6) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 119.0(6) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? N1 C15 C14 121.3(6) . . ? N1 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? O1 C16 N2 129.3(5) . . ? O1 C16 N3 116.1(5) . . ? N2 C16 N3 114.7(5) . . ? C22 C17 C18 120.7(6) . . ? C22 C17 N3 120.6(6) . . ? C18 C17 N3 118.6(6) . . ? C19 C18 C17 118.5(7) . . ? C19 C18 H18 120.8 . . ? C17 C18 H18 120.8 . . ? C20 C19 C18 121.5(8) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C19 C20 C21 121.3(7) . . ? C19 C20 H20 119.3 . . ? C21 C20 H20 119.3 . . ? C20 C21 C22 119.6(8) . . ? C20 C21 H21 120.2 . . ? C22 C21 H21 120.2 . . ? C17 C22 C21 118.3(7) . . ? C17 C22 H22 120.9 . . ? C21 C22 H22 120.9 . . ? O2 C23 N4 119.3(5) . . ? O2 C23 N3 122.8(5) . . ? N4 C23 N3 117.8(5) . . ? C29 C24 C25 119.6(6) . . ? C29 C24 N4 121.9(6) . . ? C25 C24 N4 118.4(6) . . ? C26 C25 C24 120.3(8) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C27 C26 C25 119.9(8) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C28 C27 C26 120.5(7) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C27 C28 C29 120.8(8) . . ? C27 C28 H28 119.6 . . ? C29 C28 H28 119.6 . . ? C24 C29 C28 118.8(7) . . ? C24 C29 H29 120.6 . . ? C28 C29 H29 120.6 . . ? C33 O3 C30 93.4(16) . . ? C31 C30 O3 109.9(18) . . ? C31 C30 H30A 109.7 . . ? O3 C30 H30A 109.7 . . ? C31 C30 H30B 109.7 . . ? O3 C30 H30B 109.7 . . ? H30A C30 H30B 108.2 . . ? C30 C31 C32 106.2(15) . . ? C30 C31 H31A 110.5 . . ? C32 C31 H31A 110.5 . . ? C30 C31 H31B 110.5 . . ? C32 C31 H31B 110.5 . . ? H31A C31 H31B 108.7 . . ? C31 C32 C33 97.0(14) . . ? C31 C32 H32A 112.4 . . ? C33 C32 H32A 112.4 . . ? C31 C32 H32B 112.4 . . ? C33 C32 H32B 112.4 . . ? H32A C32 H32B 109.9 . . ? O3 C33 C32 117.0(19) . . ? O3 C33 H33A 108.1 . . ? C32 C33 H33A 108.1 . . ? O3 C33 H33B 108.1 . . ? C32 C33 H33B 108.1 . . ? H33A C33 H33B 107.3 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4' O3 0.85(2) 2.31(6) 2.918(9) 128(6) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.021 _refine_diff_density_min -1.060 _refine_diff_density_rms 0.089 #======================================END data_f80115b _database_code_depnum_ccdc_archive 'CCDC 723137' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H33 Gd N4 O3' _chemical_formula_weight 690.88 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' Gd Gd -0.1653 3.9035 '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 9.811(6) _cell_length_b 11.851(7) _cell_length_c 26.149(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.670(7) _cell_angle_gamma 90.00 _cell_volume 3030(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4882 _cell_measurement_theta_min 2.284 _cell_measurement_theta_max 24.152 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1388 _exptl_absorpt_coefficient_mu 2.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6642 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '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_% ? _diffrn_reflns_number 12065 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5279 _reflns_number_gt 4333 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0761P)^2^+2.9678P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5279 _refine_ls_number_parameters 348 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Gd1 Gd 1.05777(2) 0.41645(2) 0.157715(10) 0.03552(12) Uani 1 1 d . . . O1 O 0.9533(4) 0.5865(3) 0.1371(2) 0.0539(11) Uani 1 1 d . . . O2 O 0.5902(5) 0.4110(3) 0.1387(2) 0.0633(13) Uani 1 1 d . . . N1 N 0.9359(5) 0.2582(4) 0.1960(2) 0.0488(12) Uani 1 1 d . . . N2 N 0.8158(5) 0.4085(4) 0.1682(2) 0.0434(11) Uani 1 1 d . . . N3 N 0.7183(5) 0.5613(4) 0.1212(2) 0.0423(11) Uani 1 1 d . . . N4 N 0.8252(5) 0.7323(4) 0.1100(2) 0.0563(14) Uani 1 1 d D . . H4' H 0.743(3) 0.756(5) 0.103(3) 0.068 Uiso 1 1 d D . . C1 C 1.1510(12) 0.4113(12) 0.2586(3) 0.103(4) Uani 1 1 d . . . H1A H 1.1078 0.3722 0.2861 0.124 Uiso 1 1 calc R . . C2 C 1.2543(10) 0.3703(8) 0.2319(4) 0.084(3) Uani 1 1 d . . . H2A H 1.2977 0.2964 0.2376 0.101 Uiso 1 1 calc R . . C3 C 1.3063(8) 0.4564(8) 0.2048(3) 0.076(2) Uani 1 1 d . . . H3A H 1.3924 0.4536 0.1883 0.091 Uiso 1 1 calc R . . C4 C 1.2351(9) 0.5508(7) 0.2128(3) 0.076(2) Uani 1 1 d . . . H4A H 1.2613 0.6269 0.2026 0.091 Uiso 1 1 calc R . . C5 C 1.1381(9) 0.5273(11) 0.2463(4) 0.095(3) Uani 1 1 d . . . H5A H 1.0840 0.5829 0.2637 0.114 Uiso 1 1 calc R . . C6 C 1.1119(12) 0.4327(7) 0.0599(3) 0.081(3) Uani 1 1 d . . . H6A H 1.1161 0.5039 0.0410 0.097 Uiso 1 1 calc R . . C7 C 1.2183(10) 0.3801(10) 0.0818(4) 0.089(3) Uani 1 1 d . . . H7A H 1.3135 0.4048 0.0814 0.107 Uiso 1 1 calc R . . C8 C 1.1764(12) 0.2753(8) 0.0959(3) 0.089(3) Uani 1 1 d . . . H8A H 1.2380 0.2138 0.1076 0.107 Uiso 1 1 calc R . . C9 C 1.0405(11) 0.2631(7) 0.0830(3) 0.082(3) Uani 1 1 d . . . H9A H 0.9888 0.1923 0.0827 0.098 Uiso 1 1 calc R . . C10 C 0.9967(10) 0.3643(10) 0.0596(3) 0.088(3) Uani 1 1 d . . . H10A H 0.9088 0.3772 0.0399 0.105 Uiso 1 1 calc R . . C11 C 0.9549(7) 0.1579(5) 0.2198(3) 0.0563(17) Uani 1 1 d . . . H11A H 1.0406 0.1242 0.2205 0.068 Uiso 1 1 calc R . . C12 C 0.8542(9) 0.1041(6) 0.2427(3) 0.069(2) Uani 1 1 d . . . H12A H 0.8704 0.0352 0.2591 0.083 Uiso 1 1 calc R . . C13 C 0.7269(8) 0.1546(7) 0.2409(3) 0.072(2) Uani 1 1 d . . . H13A H 0.6564 0.1196 0.2566 0.086 Uiso 1 1 calc R . . C14 C 0.7036(7) 0.2554(6) 0.2163(3) 0.0619(18) Uani 1 1 d . . . H14A H 0.6179 0.2894 0.2150 0.074 Uiso 1 1 calc R . . C15 C 0.8105(6) 0.3060(5) 0.1932(2) 0.0429(13) Uani 1 1 d . . . C16 C 0.7022(6) 0.4510(5) 0.1439(2) 0.0417(13) Uani 1 1 d . . . C17 C 0.5986(6) 0.6082(5) 0.0933(3) 0.0463(15) Uani 1 1 d . . . C18 C 0.5900(8) 0.6087(6) 0.0408(3) 0.0651(19) Uani 1 1 d . . . H18A H 0.6618 0.5798 0.0237 0.078 Uiso 1 1 calc R . . C19 C 0.4767(9) 0.6513(7) 0.0131(3) 0.077(2) Uani 1 1 d . . . H19A H 0.4719 0.6535 -0.0225 0.092 Uiso 1 1 calc R . . C20 C 0.3707(8) 0.6906(7) 0.0392(4) 0.080(3) Uani 1 1 d . . . H20A H 0.2924 0.7177 0.0208 0.096 Uiso 1 1 calc R . . C21 C 0.3773(7) 0.6908(6) 0.0907(4) 0.073(2) Uani 1 1 d . . . H21A H 0.3039 0.7179 0.1075 0.088 Uiso 1 1 calc R . . C22 C 0.4936(7) 0.6506(6) 0.1193(3) 0.0622(19) Uani 1 1 d . . . H22A H 0.4999 0.6524 0.1550 0.075 Uiso 1 1 calc R . . C23 C 0.8386(6) 0.6246(5) 0.1234(2) 0.0415(13) Uani 1 1 d . . . C24 C 0.9387(6) 0.8028(5) 0.1016(3) 0.0479(15) Uani 1 1 d . . . C25 C 0.9708(8) 0.8209(6) 0.0524(3) 0.0630(18) Uani 1 1 d . . . H25A H 0.9223 0.7836 0.0254 0.076 Uiso 1 1 calc R . . C26 C 1.0744(9) 0.8939(7) 0.0426(4) 0.082(2) Uani 1 1 d . . . H26A H 1.0967 0.9058 0.0091 0.098 Uiso 1 1 calc R . . C27 C 1.1434(8) 0.9481(6) 0.0819(5) 0.084(3) Uani 1 1 d . . . H27A H 1.2124 0.9985 0.0752 0.101 Uiso 1 1 calc R . . C28 C 1.1139(9) 0.9305(6) 0.1317(4) 0.080(3) Uani 1 1 d . . . H28A H 1.1629 0.9679 0.1585 0.097 Uiso 1 1 calc R . . C29 C 1.0103(8) 0.8563(6) 0.1413(3) 0.068(2) Uani 1 1 d . . . H29A H 0.9896 0.8429 0.1749 0.082 Uiso 1 1 calc R . . O3 O 0.6414(10) -0.0788(7) 0.0894(4) 0.132(3) Uiso 1 1 d . . . C30 C 0.560(2) -0.0365(19) 0.1215(9) 0.226(8) Uiso 1 1 d . . . H30A H 0.6031 -0.0393 0.1561 0.271 Uiso 1 1 calc R . . H30B H 0.4760 -0.0806 0.1205 0.271 Uiso 1 1 calc R . . C31 C 0.5256(19) 0.0862(13) 0.1066(7) 0.169(6) Uiso 1 1 d . . . H31A H 0.4456 0.0907 0.0823 0.203 Uiso 1 1 calc R . . H31B H 0.5108 0.1316 0.1365 0.203 Uiso 1 1 calc R . . C32 C 0.6422(18) 0.1191(15) 0.0845(7) 0.175(6) Uiso 1 1 d . . . H32A H 0.6215 0.1413 0.0490 0.210 Uiso 1 1 calc R . . H32B H 0.6872 0.1812 0.1032 0.210 Uiso 1 1 calc R . . C33 C 0.720(3) 0.024(2) 0.0880(9) 0.244(10) Uiso 1 1 d . . . H33A H 0.7820 0.0289 0.1188 0.293 Uiso 1 1 calc R . . H33B H 0.7752 0.0217 0.0588 0.293 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 Gd1 0.03191(17) 0.04052(18) 0.03401(18) 0.00184(11) 0.00195(11) 0.00132(11) O1 0.039(2) 0.044(2) 0.078(3) 0.008(2) -0.002(2) 0.0005(18) O2 0.038(2) 0.053(3) 0.098(4) 0.019(2) -0.005(2) -0.008(2) N1 0.049(3) 0.047(3) 0.050(3) 0.016(2) 0.001(2) 0.003(2) N2 0.035(2) 0.046(3) 0.050(3) 0.009(2) 0.005(2) 0.004(2) N3 0.034(2) 0.042(3) 0.050(3) 0.008(2) 0.000(2) 0.0017(19) N4 0.040(3) 0.044(3) 0.084(4) 0.015(3) -0.001(3) 0.005(2) C1 0.095(8) 0.171(12) 0.039(5) 0.017(6) -0.022(5) -0.057(8) C2 0.086(6) 0.088(6) 0.070(6) 0.007(5) -0.043(5) 0.012(5) C3 0.043(4) 0.109(6) 0.072(6) -0.020(5) -0.011(4) 0.000(4) C4 0.065(5) 0.078(5) 0.079(6) -0.011(4) -0.024(4) -0.015(4) C5 0.058(5) 0.157(9) 0.067(6) -0.057(6) -0.015(4) 0.020(6) C6 0.127(8) 0.073(5) 0.047(5) 0.008(4) 0.029(5) -0.006(5) C7 0.072(6) 0.128(8) 0.072(6) -0.019(6) 0.034(5) -0.008(6) C8 0.127(9) 0.082(6) 0.060(5) -0.007(4) 0.024(6) 0.044(6) C9 0.115(8) 0.071(5) 0.063(5) -0.032(4) 0.028(5) -0.021(5) C10 0.082(6) 0.134(8) 0.044(5) -0.026(5) -0.014(4) 0.016(6) C11 0.058(4) 0.058(4) 0.052(4) 0.020(3) -0.002(3) 0.008(3) C12 0.082(6) 0.051(4) 0.073(5) 0.028(4) 0.000(4) -0.010(4) C13 0.072(5) 0.078(5) 0.067(5) 0.026(4) 0.015(4) -0.019(4) C14 0.046(3) 0.075(4) 0.066(5) 0.018(4) 0.005(3) -0.008(3) C15 0.044(3) 0.046(3) 0.039(3) 0.005(3) 0.003(3) -0.003(3) C16 0.040(3) 0.040(3) 0.046(4) 0.001(2) 0.009(3) 0.004(2) C17 0.035(3) 0.037(3) 0.066(4) 0.006(3) 0.001(3) 0.000(2) C18 0.067(5) 0.066(4) 0.060(5) 0.000(4) -0.007(4) 0.014(4) C19 0.082(6) 0.069(5) 0.074(6) 0.006(4) -0.021(5) 0.005(4) C20 0.060(5) 0.067(5) 0.108(8) 0.023(5) -0.032(5) 0.002(4) C21 0.044(4) 0.071(5) 0.105(7) 0.023(5) 0.010(4) 0.016(3) C22 0.050(4) 0.060(4) 0.078(5) 0.016(4) 0.012(4) 0.011(3) C23 0.041(3) 0.042(3) 0.041(3) 0.001(2) 0.005(3) 0.003(3) C24 0.046(3) 0.032(3) 0.065(4) 0.008(3) -0.001(3) 0.004(2) C25 0.065(5) 0.069(4) 0.056(5) -0.005(3) 0.009(4) -0.003(4) C26 0.079(6) 0.085(6) 0.085(6) 0.008(5) 0.028(5) -0.007(5) C27 0.055(5) 0.049(4) 0.148(10) 0.013(5) 0.007(5) -0.007(3) C28 0.067(5) 0.064(5) 0.104(8) -0.006(5) -0.027(5) -0.014(4) C29 0.072(5) 0.072(5) 0.058(5) 0.013(4) -0.013(4) -0.003(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 Gd1 O1 2.304(4) . ? Gd1 N2 2.414(5) . ? Gd1 N1 2.479(5) . ? Gd1 C8 2.659(8) . ? Gd1 C10 2.660(8) . ? Gd1 C6 2.662(8) . ? Gd1 C9 2.664(7) . ? Gd1 C7 2.667(8) . ? Gd1 C2 2.678(7) . ? Gd1 C3 2.683(7) . ? Gd1 C4 2.689(7) . ? Gd1 C1 2.722(8) . ? O1 C23 1.238(7) . ? O2 C16 1.194(7) . ? N1 C11 1.347(7) . ? N1 C15 1.351(7) . ? N2 C16 1.336(7) . ? N2 C15 1.382(7) . ? N3 C23 1.396(7) . ? N3 C17 1.442(8) . ? N3 C16 1.449(7) . ? N4 C23 1.327(7) . ? N4 C24 1.423(8) . ? N4 H4' 0.86(2) . ? C1 C2 1.366(14) . ? C1 C5 1.415(14) . ? C1 H1A 0.9800 . ? C2 C3 1.365(13) . ? C2 H2A 0.9800 . ? C3 C4 1.344(11) . ? C3 H3A 0.9800 . ? C4 C5 1.372(13) . ? C4 H4A 0.9800 . ? C5 H5A 0.9800 . ? C6 C7 1.307(13) . ? C6 C10 1.391(13) . ? C6 H6A 0.9800 . ? C7 C8 1.369(13) . ? C7 H7A 0.9800 . ? C8 C9 1.356(12) . ? C8 H8A 0.9800 . ? C9 C10 1.397(13) . ? C9 H9A 0.9800 . ? C10 H10A 0.9800 . ? C11 C12 1.355(10) . ? C11 H11A 0.9300 . ? C12 C13 1.382(11) . ? C12 H12A 0.9300 . ? C13 C14 1.368(10) . ? C13 H13A 0.9300 . ? C14 C15 1.388(8) . ? C14 H14A 0.9300 . ? C17 C18 1.368(10) . ? C17 C22 1.376(9) . ? C18 C19 1.373(10) . ? C18 H18A 0.9300 . ? C19 C20 1.371(12) . ? C19 H19A 0.9300 . ? C20 C21 1.343(12) . ? C20 H20A 0.9300 . ? C21 C22 1.397(10) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? C24 C29 1.362(10) . ? C24 C25 1.366(9) . ? C25 C26 1.375(10) . ? C25 H25A 0.9300 . ? C26 C27 1.348(13) . ? C26 H26A 0.9300 . ? C27 C28 1.370(14) . ? C27 H27A 0.9300 . ? C28 C29 1.383(12) . ? C28 H28A 0.9300 . ? C29 H29A 0.9300 . ? O3 C30 1.31(2) . ? O3 C33 1.45(2) . ? C30 C31 1.54(2) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.38(2) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.36(2) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Gd1 N2 68.79(15) . . ? O1 Gd1 N1 122.43(16) . . ? N2 Gd1 N1 54.07(15) . . ? O1 Gd1 C8 128.0(2) . . ? N2 Gd1 C8 121.9(3) . . ? N1 Gd1 C8 91.1(3) . . ? O1 Gd1 C10 85.2(3) . . ? N2 Gd1 C10 87.4(3) . . ? N1 Gd1 C10 97.8(3) . . ? C8 Gd1 C10 48.9(3) . . ? O1 Gd1 C6 80.3(2) . . ? N2 Gd1 C6 112.8(3) . . ? N1 Gd1 C6 125.7(2) . . ? C8 Gd1 C6 47.9(3) . . ? C10 Gd1 C6 30.3(3) . . ? O1 Gd1 C9 115.1(3) . . ? N2 Gd1 C9 93.0(3) . . ? N1 Gd1 C9 77.1(2) . . ? C8 Gd1 C9 29.5(3) . . ? C10 Gd1 C9 30.4(3) . . ? C6 Gd1 C9 49.5(3) . . ? O1 Gd1 C7 104.2(3) . . ? N2 Gd1 C7 136.4(3) . . ? N1 Gd1 C7 120.8(3) . . ? C8 Gd1 C7 29.8(3) . . ? C10 Gd1 C7 49.1(3) . . ? C6 Gd1 C7 28.4(3) . . ? C9 Gd1 C7 49.5(3) . . ? O1 Gd1 C2 128.9(2) . . ? N2 Gd1 C2 124.5(3) . . ? N1 Gd1 C2 84.0(3) . . ? C8 Gd1 C2 89.2(3) . . ? C10 Gd1 C2 138.0(3) . . ? C6 Gd1 C2 121.5(4) . . ? C9 Gd1 C2 113.0(3) . . ? C7 Gd1 C2 94.1(4) . . ? O1 Gd1 C3 108.9(2) . . ? N2 Gd1 C3 145.1(2) . . ? N1 Gd1 C3 113.5(2) . . ? C8 Gd1 C3 87.9(3) . . ? C10 Gd1 C3 127.5(3) . . ? C6 Gd1 C3 100.6(3) . . ? C9 Gd1 C3 117.3(3) . . ? C7 Gd1 C3 78.5(3) . . ? C2 Gd1 C3 29.5(3) . . ? O1 Gd1 C4 82.2(2) . . ? N2 Gd1 C4 124.1(2) . . ? N1 Gd1 C4 122.9(2) . . ? C8 Gd1 C4 113.7(3) . . ? C10 Gd1 C4 137.7(3) . . ? C6 Gd1 C4 107.5(3) . . ? C9 Gd1 C4 142.8(3) . . ? C7 Gd1 C4 95.7(3) . . ? C2 Gd1 C4 48.4(3) . . ? C3 Gd1 C4 29.0(2) . . ? O1 Gd1 C1 110.8(3) . . ? N2 Gd1 C1 98.3(3) . . ? N1 Gd1 C1 74.1(2) . . ? C8 Gd1 C1 116.5(4) . . ? C10 Gd1 C1 164.0(4) . . ? C6 Gd1 C1 148.8(4) . . ? C9 Gd1 C1 133.8(4) . . ? C7 Gd1 C1 123.1(4) . . ? C2 Gd1 C1 29.3(3) . . ? C3 Gd1 C1 48.5(3) . . ? C4 Gd1 C1 48.9(3) . . ? C23 O1 Gd1 139.7(4) . . ? C11 N1 C15 119.1(5) . . ? C11 N1 Gd1 143.2(4) . . ? C15 N1 Gd1 97.3(3) . . ? C16 N2 C15 119.7(5) . . ? C16 N2 Gd1 136.1(4) . . ? C15 N2 Gd1 99.4(3) . . ? C23 N3 C17 117.7(5) . . ? C23 N3 C16 126.0(5) . . ? C17 N3 C16 116.3(5) . . ? C23 N4 C24 122.9(5) . . ? C23 N4 H4' 116(5) . . ? C24 N4 H4' 121(5) . . ? C2 C1 C5 106.6(9) . . ? C2 C1 Gd1 73.6(5) . . ? C5 C1 Gd1 75.0(5) . . ? C2 C1 H1A 126.1 . . ? C5 C1 H1A 126.1 . . ? Gd1 C1 H1A 126.1 . . ? C3 C2 C1 108.8(9) . . ? C3 C2 Gd1 75.5(4) . . ? C1 C2 Gd1 77.1(5) . . ? C3 C2 H2A 124.9 . . ? C1 C2 H2A 124.9 . . ? Gd1 C2 H2A 124.9 . . ? C4 C3 C2 108.7(8) . . ? C4 C3 Gd1 75.7(4) . . ? C2 C3 Gd1 75.0(4) . . ? C4 C3 H3A 125.1 . . ? C2 C3 H3A 125.1 . . ? Gd1 C3 H3A 125.1 . . ? C3 C4 C5 109.0(9) . . ? C3 C4 Gd1 75.3(4) . . ? C5 C4 Gd1 76.7(5) . . ? C3 C4 H4A 124.8 . . ? C5 C4 H4A 124.8 . . ? Gd1 C4 H4A 124.8 . . ? C4 C5 C1 106.8(9) . . ? C4 C5 Gd1 73.9(5) . . ? C1 C5 Gd1 74.9(5) . . ? C4 C5 H5A 126.1 . . ? C1 C5 H5A 126.1 . . ? Gd1 C5 H5A 126.1 . . ? C7 C6 C10 110.1(9) . . ? C7 C6 Gd1 76.1(5) . . ? C10 C6 Gd1 74.8(5) . . ? C7 C6 H6A 124.5 . . ? C10 C6 H6A 124.5 . . ? Gd1 C6 H6A 124.5 . . ? C6 C7 C8 107.7(9) . . ? C6 C7 Gd1 75.6(5) . . ? C8 C7 Gd1 74.8(5) . . ? C6 C7 H7A 125.5 . . ? C8 C7 H7A 125.5 . . ? Gd1 C7 H7A 125.5 . . ? C9 C8 C7 109.9(9) . . ? C9 C8 Gd1 75.4(5) . . ? C7 C8 Gd1 75.5(5) . . ? C9 C8 H8A 124.6 . . ? C7 C8 H8A 124.6 . . ? Gd1 C8 H8A 124.6 . . ? C8 C9 C10 106.2(8) . . ? C8 C9 Gd1 75.0(5) . . ? C10 C9 Gd1 74.6(4) . . ? C8 C9 H9A 126.2 . . ? C10 C9 H9A 126.2 . . ? Gd1 C9 H9A 126.2 . . ? C6 C10 C9 106.1(9) . . ? C6 C10 Gd1 74.9(5) . . ? C9 C10 Gd1 75.0(5) . . ? C6 C10 H10A 126.2 . . ? C9 C10 H10A 126.2 . . ? Gd1 C10 H10A 126.2 . . ? N1 C11 C12 122.7(6) . . ? N1 C11 H11A 118.6 . . ? C12 C11 H11A 118.6 . . ? C11 C12 C13 118.1(6) . . ? C11 C12 H12A 121.0 . . ? C13 C12 H12A 121.0 . . ? C14 C13 C12 120.6(6) . . ? C14 C13 H13A 119.7 . . ? C12 C13 H13A 119.7 . . ? C13 C14 C15 118.6(7) . . ? C13 C14 H14A 120.7 . . ? C15 C14 H14A 120.7 . . ? N1 C15 N2 109.0(5) . . ? N1 C15 C14 120.8(5) . . ? N2 C15 C14 130.0(6) . . ? N1 C15 Gd1 55.9(3) . . ? N2 C15 Gd1 53.3(3) . . ? C14 C15 Gd1 172.4(5) . . ? O2 C16 N2 128.8(5) . . ? O2 C16 N3 116.3(5) . . ? N2 C16 N3 114.9(5) . . ? C18 C17 C22 120.5(6) . . ? C18 C17 N3 119.4(6) . . ? C22 C17 N3 120.1(6) . . ? C17 C18 C19 120.8(8) . . ? C17 C18 H18A 119.6 . . ? C19 C18 H18A 119.6 . . ? C20 C19 C18 118.5(8) . . ? C20 C19 H19A 120.7 . . ? C18 C19 H19A 120.7 . . ? C21 C20 C19 121.5(7) . . ? C21 C20 H20A 119.2 . . ? C19 C20 H20A 119.2 . . ? C20 C21 C22 120.5(7) . . ? C20 C21 H21A 119.8 . . ? C22 C21 H21A 119.8 . . ? C17 C22 C21 118.1(8) . . ? C17 C22 H22A 120.9 . . ? C21 C22 H22A 120.9 . . ? O1 C23 N4 119.7(5) . . ? O1 C23 N3 124.2(5) . . ? N4 C23 N3 116.1(5) . . ? C29 C24 C25 120.1(7) . . ? C29 C24 N4 121.1(7) . . ? C25 C24 N4 118.8(6) . . ? C24 C25 C26 120.4(8) . . ? C24 C25 H25A 119.8 . . ? C26 C25 H25A 119.8 . . ? C27 C26 C25 119.3(9) . . ? C27 C26 H26A 120.3 . . ? C25 C26 H26A 120.3 . . ? C26 C27 C28 121.4(8) . . ? C26 C27 H27A 119.3 . . ? C28 C27 H27A 119.3 . . ? C27 C28 C29 119.0(8) . . ? C27 C28 H28A 120.5 . . ? C29 C28 H28A 120.5 . . ? C24 C29 C28 119.8(8) . . ? C24 C29 H29A 120.1 . . ? C28 C29 H29A 120.1 . . ? C30 O3 C33 92.9(15) . . ? O3 C30 C31 109.4(18) . . ? O3 C30 H30A 109.8 . . ? C31 C30 H30A 109.8 . . ? O3 C30 H30B 109.8 . . ? C31 C30 H30B 109.8 . . ? H30A C30 H30B 108.2 . . ? C32 C31 C30 101.8(16) . . ? C32 C31 H31A 111.4 . . ? C30 C31 H31A 111.4 . . ? C32 C31 H31B 111.4 . . ? C30 C31 H31B 111.4 . . ? H31A C31 H31B 109.3 . . ? C33 C32 C31 102.8(18) . . ? C33 C32 H32A 111.2 . . ? C31 C32 H32A 111.2 . . ? C33 C32 H32B 111.2 . . ? C31 C32 H32B 111.2 . . ? H32A C32 H32B 109.1 . . ? C32 C33 O3 114(2) . . ? C32 C33 H33A 108.8 . . ? O3 C33 H33A 108.8 . . ? C32 C33 H33B 108.8 . . ? O3 C33 H33B 108.8 . . ? H33A C33 H33B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.983 _refine_diff_density_min -0.851 _refine_diff_density_rms 0.112 #======================================END data_f80721d _database_code_depnum_ccdc_archive 'CCDC 723138' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common nsy _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H33 Er N4 O3' _chemical_formula_weight 700.89 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' Er Er -0.2586 4.9576 '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 9.799(3) _cell_length_b 11.819(3) _cell_length_c 26.044(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.795(4) _cell_angle_gamma 90.00 _cell_volume 3005.6(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6020 _cell_measurement_theta_min 2.706 _cell_measurement_theta_max 25.1955 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1404 _exptl_absorpt_coefficient_mu 2.832 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4838 _exptl_absorpt_correction_T_max 0.6761 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '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_% ? _diffrn_reflns_number 14254 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.01 _reflns_number_total 6428 _reflns_number_gt 4691 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _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^)+(0.0340P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6428 _refine_ls_number_parameters 373 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0708 _refine_ls_wR_factor_gt 0.0678 _refine_ls_goodness_of_fit_ref 0.911 _refine_ls_restrained_S_all 0.914 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Er1 Er 1.056053(16) 0.583774(15) 0.157857(6) 0.03579(7) Uani 1 1 d . . . N1 N 0.9418(3) 0.7422(3) 0.19620(12) 0.0431(8) Uani 1 1 d . . . N2 N 0.8196(3) 0.5922(3) 0.16926(12) 0.0405(7) Uani 1 1 d . . . N3 N 0.7224(3) 0.4401(3) 0.12125(13) 0.0415(8) Uani 1 1 d . . . N4 N 0.8288(3) 0.2691(3) 0.10971(15) 0.0550(10) Uani 1 1 d D . . H4' H 0.750(3) 0.243(4) 0.1014(16) 0.066 Uiso 1 1 d D . . O1 O 0.5919(3) 0.5905(2) 0.13935(13) 0.0601(8) Uani 1 1 d . . . O2 O 0.9567(3) 0.4158(2) 0.13680(12) 0.0500(7) Uani 1 1 d . . . C1 C 1.1079(9) 0.5663(5) 0.0615(2) 0.086(2) Uani 1 1 d . . . H1 H 1.1090 0.4933 0.0482 0.104 Uiso 1 1 calc R . . C2 C 1.2148(7) 0.6199(7) 0.0836(2) 0.089(2) Uani 1 1 d . . . H2 H 1.3032 0.5910 0.0887 0.106 Uiso 1 1 calc R . . C3 C 1.1744(7) 0.7243(6) 0.0977(2) 0.0831(19) Uani 1 1 d . . . H3 H 1.2308 0.7792 0.1139 0.100 Uiso 1 1 calc R . . C4 C 1.0367(7) 0.7356(5) 0.0842(2) 0.0809(18) Uani 1 1 d . . . H4 H 0.9827 0.7985 0.0896 0.097 Uiso 1 1 calc R . . C5 C 0.9938(6) 0.6347(7) 0.0611(2) 0.087(2) Uani 1 1 d . . . H5 H 0.9054 0.6167 0.0478 0.104 Uiso 1 1 calc R . . C6 C 1.1327(6) 0.4674(7) 0.2425(2) 0.0849(19) Uani 1 1 d . . . H6 H 1.0712 0.4142 0.2533 0.102 Uiso 1 1 calc R . . C7 C 1.1405(7) 0.5797(8) 0.2571(2) 0.098(3) Uani 1 1 d . . . H7 H 1.0850 0.6162 0.2792 0.118 Uiso 1 1 calc R . . C8 C 1.2476(7) 0.6281(6) 0.2325(3) 0.090(2) Uani 1 1 d . . . H8 H 1.2768 0.7029 0.2352 0.108 Uiso 1 1 calc R . . C9 C 1.3014(5) 0.5455(6) 0.2037(2) 0.0785(18) Uani 1 1 d . . . H9 H 1.3744 0.5548 0.1835 0.094 Uiso 1 1 calc R . . C10 C 1.2321(6) 0.4483(5) 0.2092(2) 0.0719(15) Uani 1 1 d . . . H10 H 1.2488 0.3799 0.1932 0.086 Uiso 1 1 calc R . . C11 C 0.8160(4) 0.6958(3) 0.19362(14) 0.0409(9) Uani 1 1 d . . . C12 C 0.7094(4) 0.7476(4) 0.21672(16) 0.0588(12) Uani 1 1 d . . . H12 H 0.6229 0.7150 0.2155 0.071 Uiso 1 1 calc R . . C13 C 0.7371(5) 0.8500(5) 0.24159(18) 0.0686(15) Uani 1 1 d . . . H13 H 0.6682 0.8862 0.2578 0.082 Uiso 1 1 calc R . . C14 C 0.8630(5) 0.8979(4) 0.24255(18) 0.0631(13) Uani 1 1 d . . . H14 H 0.8804 0.9677 0.2583 0.076 Uiso 1 1 calc R . . C15 C 0.9637(5) 0.8416(4) 0.21995(16) 0.0547(12) Uani 1 1 d . . . H15 H 1.0506 0.8735 0.2211 0.066 Uiso 1 1 calc R . . C16 C 0.7053(4) 0.5487(3) 0.14454(15) 0.0416(10) Uani 1 1 d . . . C17 C 0.6015(4) 0.3933(3) 0.09261(17) 0.0452(10) Uani 1 1 d . . . C18 C 0.5957(5) 0.3926(4) 0.03994(18) 0.0632(13) Uani 1 1 d . . . H18 H 0.6681 0.4206 0.0228 0.076 Uiso 1 1 calc R . . C19 C 0.4807(6) 0.3496(5) 0.0128(2) 0.0749(15) Uani 1 1 d . . . H19 H 0.4768 0.3472 -0.0230 0.090 Uiso 1 1 calc R . . C20 C 0.3741(6) 0.3110(5) 0.0368(3) 0.0800(17) Uani 1 1 d . . . H20 H 0.2965 0.2840 0.0177 0.096 Uiso 1 1 calc R . . C21 C 0.3796(5) 0.3116(4) 0.0890(2) 0.0761(16) Uani 1 1 d . . . H21 H 0.3061 0.2839 0.1057 0.091 Uiso 1 1 calc R . . C22 C 0.4944(5) 0.3532(4) 0.1177(2) 0.0618(13) Uani 1 1 d . . . H22 H 0.4984 0.3537 0.1536 0.074 Uiso 1 1 calc R . . C23 C 0.8415(4) 0.3765(3) 0.12319(15) 0.0412(9) Uani 1 1 d . . . C24 C 0.9426(4) 0.1986(3) 0.10119(17) 0.0438(10) Uani 1 1 d . . . C25 C 0.9748(5) 0.1803(4) 0.05146(18) 0.0643(13) Uani 1 1 d . . . H25 H 0.9261 0.2179 0.0244 0.077 Uiso 1 1 calc R . . C26 C 1.0771(6) 0.1081(5) 0.0413(2) 0.0779(16) Uani 1 1 d . . . H26 H 1.0985 0.0969 0.0076 0.093 Uiso 1 1 calc R . . C27 C 1.1481(6) 0.0522(5) 0.0806(3) 0.0813(18) Uani 1 1 d . . . H27 H 1.2163 0.0012 0.0736 0.098 Uiso 1 1 calc R . . C28 C 1.1195(6) 0.0707(4) 0.1301(3) 0.0805(17) Uani 1 1 d . . . H28 H 1.1700 0.0338 0.1570 0.097 Uiso 1 1 calc R . . C29 C 1.0147(5) 0.1449(5) 0.14077(19) 0.0669(14) Uani 1 1 d . . . H29 H 0.9945 0.1574 0.1746 0.080 Uiso 1 1 calc R . . O3 O 0.6439(6) 1.0818(4) 0.0904(3) 0.144(2) Uani 1 1 d D . . C30 C 0.6961(16) 0.9922(9) 0.0732(8) 0.432(17) Uani 1 1 d DU . . H30A H 0.7930 0.9933 0.0845 0.518 Uiso 1 1 calc R . . H30B H 0.6891 0.9985 0.0359 0.518 Uiso 1 1 calc R . . C31 C 0.6464(12) 0.8848(8) 0.0851(4) 0.180(4) Uani 1 1 d DU . . H31A H 0.6355 0.8358 0.0551 0.216 Uiso 1 1 calc R . . H31B H 0.7033 0.8479 0.1124 0.216 Uiso 1 1 calc R . . C32 C 0.5223(9) 0.9197(8) 0.1011(7) 0.264(9) Uani 1 1 d DU . . H32A H 0.4939 0.8734 0.1290 0.316 Uiso 1 1 calc R . . H32B H 0.4508 0.9201 0.0730 0.316 Uiso 1 1 calc R . . C33 C 0.5594(14) 1.0336(9) 0.1182(5) 0.251(7) Uani 1 1 d DU . . H33A H 0.4770 1.0792 0.1177 0.301 Uiso 1 1 calc R . . H33B H 0.5994 1.0303 0.1535 0.301 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 Er1 0.03123(10) 0.04051(11) 0.03527(10) -0.00170(9) 0.00062(6) -0.00072(9) N1 0.0400(18) 0.045(2) 0.0434(18) -0.0121(16) -0.0032(15) -0.0018(17) N2 0.0348(17) 0.0415(19) 0.0447(18) -0.0123(16) 0.0012(14) -0.0005(16) N3 0.0315(17) 0.039(2) 0.053(2) -0.0068(15) -0.0025(15) -0.0011(14) N4 0.0380(19) 0.041(2) 0.085(3) -0.0182(19) -0.0031(19) -0.0034(17) O1 0.0362(15) 0.0482(19) 0.094(2) -0.0154(17) -0.0048(15) 0.0055(14) O2 0.0352(14) 0.0381(16) 0.076(2) -0.0121(15) -0.0020(14) -0.0003(13) C1 0.146(6) 0.073(4) 0.043(3) -0.006(3) 0.025(4) 0.001(4) C2 0.079(4) 0.129(6) 0.063(4) 0.020(4) 0.030(3) 0.007(4) C3 0.104(5) 0.083(5) 0.064(4) 0.012(3) 0.017(4) -0.043(4) C4 0.119(5) 0.066(4) 0.061(3) 0.027(3) 0.030(3) 0.036(4) C5 0.073(4) 0.143(6) 0.041(3) 0.030(4) -0.013(3) -0.017(4) C6 0.048(3) 0.123(5) 0.080(4) 0.056(4) -0.014(3) -0.011(3) C7 0.088(5) 0.168(8) 0.036(3) -0.006(4) -0.011(3) 0.061(5) C8 0.082(4) 0.092(5) 0.088(5) -0.009(4) -0.051(4) -0.004(4) C9 0.034(3) 0.124(5) 0.076(4) 0.036(4) -0.009(2) 0.004(3) C10 0.057(3) 0.071(4) 0.084(4) 0.014(3) -0.015(3) 0.018(3) C11 0.036(2) 0.048(2) 0.039(2) -0.0030(18) 0.0004(18) 0.0040(18) C12 0.045(2) 0.071(3) 0.060(3) -0.013(3) 0.006(2) 0.006(3) C13 0.061(3) 0.081(4) 0.064(3) -0.030(3) 0.006(3) 0.015(3) C14 0.070(3) 0.055(3) 0.062(3) -0.026(2) -0.004(3) 0.006(3) C15 0.051(3) 0.059(3) 0.054(3) -0.020(2) -0.002(2) -0.005(2) C16 0.035(2) 0.043(2) 0.047(2) 0.0017(18) 0.0038(18) -0.0021(18) C17 0.037(2) 0.037(3) 0.061(3) -0.0074(19) -0.004(2) -0.0020(18) C18 0.067(3) 0.066(3) 0.055(3) -0.001(2) -0.006(2) -0.012(3) C19 0.082(4) 0.065(4) 0.072(4) -0.004(3) -0.024(3) -0.008(3) C20 0.059(3) 0.068(4) 0.108(5) -0.027(3) -0.025(3) -0.006(3) C21 0.048(3) 0.070(4) 0.111(5) -0.028(3) 0.011(3) -0.015(3) C22 0.051(3) 0.059(3) 0.075(3) -0.019(3) 0.005(3) -0.012(2) C23 0.041(2) 0.040(2) 0.042(2) 0.0001(18) 0.0028(19) -0.0003(19) C24 0.044(2) 0.030(2) 0.056(3) -0.0040(19) -0.003(2) -0.0024(18) C25 0.067(3) 0.066(3) 0.059(3) 0.008(3) 0.003(3) 0.007(3) C26 0.077(4) 0.080(4) 0.079(4) -0.014(3) 0.023(3) 0.004(3) C27 0.061(3) 0.053(3) 0.131(6) -0.020(4) 0.013(4) 0.008(3) C28 0.073(4) 0.060(4) 0.104(5) 0.011(3) -0.028(3) 0.012(3) C29 0.071(3) 0.078(4) 0.050(3) 0.001(3) -0.008(3) 0.008(3) O3 0.121(4) 0.088(4) 0.228(7) -0.037(4) 0.054(4) -0.038(3) C30 0.50(3) 0.165(13) 0.69(4) -0.234(18) 0.43(3) -0.209(16) C31 0.198(11) 0.132(9) 0.207(11) -0.002(8) -0.007(9) 0.040(8) C32 0.087(6) 0.100(8) 0.60(3) 0.009(11) 0.020(12) -0.025(6) C33 0.308(17) 0.159(11) 0.311(17) -0.061(11) 0.183(14) -0.063(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Er1 O2 2.259(3) . ? Er1 N2 2.363(3) . ? Er1 N1 2.438(3) . ? Er1 C1 2.609(5) . ? Er1 C5 2.613(5) . ? Er1 C2 2.616(5) . ? Er1 C3 2.619(5) . ? Er1 C4 2.621(5) . ? Er1 C9 2.633(5) . ? Er1 C10 2.636(5) . ? Er1 C8 2.640(5) . ? Er1 C7 2.649(5) . ? N1 C15 1.337(5) . ? N1 C11 1.345(5) . ? N2 C16 1.346(5) . ? N2 C11 1.381(5) . ? N3 C23 1.385(5) . ? N3 C16 1.435(5) . ? N3 C17 1.456(5) . ? N4 C23 1.321(5) . ? N4 C24 1.424(5) . ? N4 H4' 0.843(19) . ? O1 C16 1.214(4) . ? O2 C23 1.244(5) . ? C1 C2 1.314(8) . ? C1 C5 1.379(9) . ? C1 H1 0.9300 . ? C2 C3 1.357(8) . ? C2 H2 0.9300 . ? C3 C4 1.372(7) . ? C3 H3 0.9300 . ? C4 C5 1.385(8) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C10 1.377(8) . ? C6 C7 1.381(8) . ? C6 H6 0.9300 . ? C7 C8 1.397(9) . ? C7 H7 0.9300 . ? C8 C9 1.363(8) . ? C8 H8 0.9300 . ? C9 C10 1.348(7) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.390(5) . ? C12 C13 1.388(6) . ? C12 H12 0.9300 . ? C13 C14 1.356(6) . ? C13 H13 0.9300 . ? C14 C15 1.363(6) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C17 C22 1.368(6) . ? C17 C18 1.368(6) . ? C18 C19 1.377(7) . ? C18 H18 0.9300 . ? C19 C20 1.341(7) . ? C19 H19 0.9300 . ? C20 C21 1.357(8) . ? C20 H20 0.9300 . ? C21 C22 1.388(6) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C24 C29 1.358(6) . ? C24 C25 1.375(6) . ? C25 C26 1.360(7) . ? C25 H25 0.9300 . ? C26 C27 1.358(8) . ? C26 H26 0.9300 . ? C27 C28 1.361(8) . ? C27 H27 0.9300 . ? C28 C29 1.396(7) . ? C28 H28 0.9300 . ? C29 H29 0.9300 . ? O3 C30 1.274(8) . ? O3 C33 1.277(8) . ? C30 C31 1.404(12) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.382(11) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.454(11) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Er1 N2 70.12(10) . . ? O2 Er1 N1 124.82(10) . . ? N2 Er1 N1 55.06(10) . . ? O2 Er1 C1 79.14(17) . . ? N2 Er1 C1 113.3(2) . . ? N1 Er1 C1 125.99(16) . . ? O2 Er1 C5 84.67(19) . . ? N2 Er1 C5 87.67(16) . . ? N1 Er1 C5 98.1(2) . . ? C1 Er1 C5 30.61(19) . . ? O2 Er1 C2 103.6(2) . . ? N2 Er1 C2 137.39(17) . . ? N1 Er1 C2 120.0(2) . . ? C1 Er1 C2 29.14(18) . . ? C5 Er1 C2 49.81(19) . . ? O2 Er1 C3 128.01(15) . . ? N2 Er1 C3 122.44(18) . . ? N1 Er1 C3 89.96(19) . . ? C1 Er1 C3 49.00(19) . . ? C5 Er1 C3 49.96(19) . . ? C2 Er1 C3 30.04(18) . . ? O2 Er1 C4 114.88(19) . . ? N2 Er1 C4 92.95(17) . . ? N1 Er1 C4 76.49(14) . . ? C1 Er1 C4 50.12(18) . . ? C5 Er1 C4 30.69(18) . . ? C2 Er1 C4 50.11(19) . . ? C3 Er1 C4 30.36(17) . . ? O2 Er1 C9 108.54(17) . . ? N2 Er1 C9 144.89(15) . . ? N1 Er1 C9 112.29(18) . . ? C1 Er1 C9 100.3(2) . . ? C5 Er1 C9 127.44(19) . . ? C2 Er1 C9 77.70(19) . . ? C3 Er1 C9 87.0(2) . . ? C4 Er1 C9 117.2(2) . . ? O2 Er1 C10 80.79(14) . . ? N2 Er1 C10 124.69(16) . . ? N1 Er1 C10 124.22(15) . . ? C1 Er1 C10 105.5(2) . . ? C5 Er1 C10 136.0(2) . . ? C2 Er1 C10 94.0(2) . . ? C3 Er1 C10 112.6(2) . . ? C4 Er1 C10 142.3(2) . . ? C9 Er1 C10 29.65(15) . . ? O2 Er1 C8 128.24(17) . . ? N2 Er1 C8 122.9(2) . . ? N1 Er1 C8 82.44(18) . . ? C1 Er1 C8 122.7(3) . . ? C5 Er1 C8 139.4(2) . . ? C2 Er1 C8 94.7(2) . . ? C3 Er1 C8 89.5(2) . . ? C4 Er1 C8 114.0(2) . . ? C9 Er1 C8 29.97(18) . . ? C10 Er1 C8 49.58(19) . . ? O2 Er1 C7 108.3(2) . . ? N2 Er1 C7 96.18(17) . . ? N1 Er1 C7 74.39(16) . . ? C1 Er1 C7 150.1(2) . . ? C5 Er1 C7 167.0(3) . . ? C2 Er1 C7 124.6(2) . . ? C3 Er1 C7 118.5(2) . . ? C4 Er1 C7 136.4(3) . . ? C9 Er1 C7 49.82(18) . . ? C10 Er1 C7 49.87(18) . . ? C8 Er1 C7 30.64(19) . . ? C15 N1 C11 119.5(3) . . ? C15 N1 Er1 143.4(3) . . ? C11 N1 Er1 96.7(2) . . ? C16 N2 C11 120.4(3) . . ? C16 N2 Er1 135.2(2) . . ? C11 N2 Er1 99.1(2) . . ? C23 N3 C16 126.7(3) . . ? C23 N3 C17 117.4(3) . . ? C16 N3 C17 116.0(3) . . ? C23 N4 C24 123.1(3) . . ? C23 N4 H4' 119(3) . . ? C24 N4 H4' 117(3) . . ? C23 O2 Er1 139.4(3) . . ? C2 C1 C5 109.7(6) . . ? C2 C1 Er1 75.7(3) . . ? C5 C1 Er1 74.9(3) . . ? C2 C1 H1 125.2 . . ? C5 C1 H1 125.2 . . ? Er1 C1 H1 116.1 . . ? C1 C2 C3 108.5(6) . . ? C1 C2 Er1 75.1(3) . . ? C3 C2 Er1 75.1(3) . . ? C1 C2 H2 125.7 . . ? C3 C2 H2 125.7 . . ? Er1 C2 H2 116.1 . . ? C2 C3 C4 108.7(6) . . ? C2 C3 Er1 74.9(3) . . ? C4 C3 Er1 74.9(3) . . ? C2 C3 H3 125.6 . . ? C4 C3 H3 125.6 . . ? Er1 C3 H3 116.6 . . ? C3 C4 C5 106.5(6) . . ? C3 C4 Er1 74.7(3) . . ? C5 C4 Er1 74.3(3) . . ? C3 C4 H4 126.7 . . ? C5 C4 H4 126.7 . . ? Er1 C4 H4 116.4 . . ? C1 C5 C4 106.5(6) . . ? C1 C5 Er1 74.5(3) . . ? C4 C5 Er1 75.0(3) . . ? C1 C5 H5 126.7 . . ? C4 C5 H5 126.7 . . ? Er1 C5 H5 116.1 . . ? C10 C6 C7 107.8(5) . . ? C10 C6 Er1 74.2(3) . . ? C7 C6 Er1 74.7(3) . . ? C10 C6 H6 126.1 . . ? C7 C6 H6 126.1 . . ? Er1 C6 H6 117.1 . . ? C6 C7 C8 107.1(6) . . ? C6 C7 Er1 75.1(3) . . ? C8 C7 Er1 74.3(3) . . ? C6 C7 H7 126.5 . . ? C8 C7 H7 126.5 . . ? Er1 C7 H7 116.3 . . ? C9 C8 C7 107.4(6) . . ? C9 C8 Er1 74.7(3) . . ? C7 C8 Er1 75.0(3) . . ? C9 C8 H8 126.3 . . ? C7 C8 H8 126.3 . . ? Er1 C8 H8 116.1 . . ? C10 C9 C8 109.3(5) . . ? C10 C9 Er1 75.3(3) . . ? C8 C9 Er1 75.3(3) . . ? C10 C9 H9 125.3 . . ? C8 C9 H9 125.3 . . ? Er1 C9 H9 116.1 . . ? C9 C10 C6 108.4(6) . . ? C9 C10 Er1 75.1(3) . . ? C6 C10 Er1 75.7(3) . . ? C9 C10 H10 125.8 . . ? C6 C10 H10 125.8 . . ? Er1 C10 H10 115.6 . . ? N1 C11 N2 109.0(3) . . ? N1 C11 C12 121.1(4) . . ? N2 C11 C12 129.7(4) . . ? N1 C11 Er1 56.05(19) . . ? N2 C11 Er1 53.05(18) . . ? C12 C11 Er1 173.0(3) . . ? C13 C12 C11 117.5(4) . . ? C13 C12 H12 121.3 . . ? C11 C12 H12 121.3 . . ? C14 C13 C12 120.9(4) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 118.6(4) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? N1 C15 C14 122.3(4) . . ? N1 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? O1 C16 N2 127.9(4) . . ? O1 C16 N3 117.1(4) . . ? N2 C16 N3 115.0(3) . . ? C22 C17 C18 120.6(4) . . ? C22 C17 N3 120.7(4) . . ? C18 C17 N3 118.7(4) . . ? C17 C18 C19 118.8(5) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C20 C19 C18 121.4(5) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C19 C20 C21 119.9(5) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C22 120.3(5) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C17 C22 C21 119.0(5) . . ? C17 C22 H22 120.5 . . ? C21 C22 H22 120.5 . . ? O2 C23 N4 119.8(4) . . ? O2 C23 N3 123.3(4) . . ? N4 C23 N3 116.8(4) . . ? C29 C24 C25 119.7(4) . . ? C29 C24 N4 121.3(4) . . ? C25 C24 N4 118.9(4) . . ? C26 C25 C24 120.8(5) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C27 C26 C25 119.9(5) . . ? C27 C26 H26 120.1 . . ? C25 C26 H26 120.1 . . ? C26 C27 C28 120.2(5) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C27 C28 C29 120.1(5) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? C24 C29 C28 119.2(5) . . ? C24 C29 H29 120.4 . . ? C28 C29 H29 120.4 . . ? C30 O3 C33 97.3(9) . . ? O3 C30 C31 121.1(10) . . ? O3 C30 H30A 107.1 . . ? C31 C30 H30A 107.1 . . ? O3 C30 H30B 107.1 . . ? C31 C30 H30B 107.1 . . ? H30A C30 H30B 106.8 . . ? C32 C31 C30 97.3(9) . . ? C32 C31 H31A 112.3 . . ? C30 C31 H31A 112.3 . . ? C32 C31 H31B 112.3 . . ? C30 C31 H31B 112.3 . . ? H31A C31 H31B 109.9 . . ? C31 C32 C33 99.5(8) . . ? C31 C32 H32A 111.9 . . ? C33 C32 H32A 111.9 . . ? C31 C32 H32B 111.9 . . ? C33 C32 H32B 111.9 . . ? H32A C32 H32B 109.6 . . ? O3 C33 C32 113.4(9) . . ? O3 C33 H33A 108.9 . . ? C32 C33 H33A 108.9 . . ? O3 C33 H33B 108.9 . . ? C32 C33 H33B 108.9 . . ? H33A C33 H33B 107.7 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N4 H4' O3 0.843(19) 2.18(3) 2.878(6) 140(4) 1_545 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 27.01 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 1.279 _refine_diff_density_min -0.730 _refine_diff_density_rms 0.096 #======================================END data_f80920c _database_code_depnum_ccdc_archive 'CCDC 745890' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H20 N2 O' _chemical_formula_weight 220.31 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.865(6) _cell_length_b 17.396(6) _cell_length_c 9.709(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.670(5) _cell_angle_gamma 90.00 _cell_volume 2728.9(17) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1539 _cell_measurement_theta_min 2.3375 _cell_measurement_theta_max 18.8085 _exptl_crystal_description cubic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.072 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9831 _exptl_absorpt_correction_T_max 0.9932 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '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_% ? _diffrn_reflns_number 11115 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.26 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4777 _reflns_number_gt 2398 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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. ; _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^)+(0.0608P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4777 _refine_ls_number_parameters 295 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1200 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1564 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 O1 O 0.29627(11) 0.70538(9) -0.22257(18) 0.0700(5) Uani 1 1 d . . . N1 N 0.27320(14) 0.75665(12) -0.0228(2) 0.0606(6) Uani 1 1 d D . . H1' H 0.2958(15) 0.7591(14) 0.0715(18) 0.073 Uiso 1 1 d D . . N2 N 0.34915(12) 0.64441(12) -0.0114(2) 0.0617(6) Uani 1 1 d . . . C1 C 0.22910(15) 0.82204(15) -0.0897(3) 0.0564(7) Uani 1 1 d . . . C2 C 0.17664(17) 0.82102(17) -0.2275(3) 0.0715(8) Uani 1 1 d . . . H2A H 0.1693 0.7761 -0.2815 0.086 Uiso 1 1 calc R . . C3 C 0.13458(18) 0.8881(2) -0.2854(3) 0.0862(10) Uani 1 1 d . . . H3A H 0.1004 0.8882 -0.3795 0.103 Uiso 1 1 calc R . . C4 C 0.1433(2) 0.95327(19) -0.2048(4) 0.0948(10) Uani 1 1 d . . . H4A H 0.1139 0.9974 -0.2427 0.114 Uiso 1 1 calc R . . C5 C 0.1947(2) 0.95347(17) -0.0699(4) 0.0973(11) Uani 1 1 d . . . H5A H 0.2010 0.9981 -0.0152 0.117 Uiso 1 1 calc R . . C6 C 0.23765(19) 0.88886(16) -0.0126(3) 0.0779(9) Uani 1 1 d . . . H6A H 0.2733 0.8903 0.0804 0.093 Uiso 1 1 calc R . . C7 C 0.30596(15) 0.70235(14) -0.0921(3) 0.0554(6) Uani 1 1 d . . . C8 C 0.38317(16) 0.58507(14) -0.0849(3) 0.0693(8) Uani 1 1 d . . . H8A H 0.4338 0.5653 -0.0193 0.083 Uiso 1 1 calc R . . H8B H 0.3972 0.6081 -0.1658 0.083 Uiso 1 1 calc R . . C9 C 0.32468(17) 0.51935(15) -0.1382(3) 0.0756(8) Uani 1 1 d . . . H9A H 0.2733 0.5391 -0.2014 0.091 Uiso 1 1 calc R . . H9B H 0.3122 0.4950 -0.0570 0.091 Uiso 1 1 calc R . . C10 C 0.3598(2) 0.45985(17) -0.2184(4) 0.1093(12) Uani 1 1 d . . . H10A H 0.3204 0.4192 -0.2505 0.164 Uiso 1 1 calc R . . H10B H 0.4101 0.4392 -0.1556 0.164 Uiso 1 1 calc R . . H10C H 0.3714 0.4835 -0.2999 0.164 Uiso 1 1 calc R . . C11 C 0.36286(17) 0.63437(15) 0.1435(3) 0.0693(8) Uani 1 1 d . . . H11A H 0.3640 0.5799 0.1652 0.083 Uiso 1 1 calc R . . H11B H 0.3169 0.6570 0.1705 0.083 Uiso 1 1 calc R . . C12 C 0.44221(18) 0.67058(18) 0.2315(3) 0.0867(9) Uani 1 1 d . . . H12A H 0.4378 0.7260 0.2222 0.104 Uiso 1 1 calc R . . H12B H 0.4873 0.6540 0.1951 0.104 Uiso 1 1 calc R . . C13 C 0.4614(2) 0.6486(2) 0.3899(3) 0.1162(13) Uani 1 1 d . . . H13A H 0.5128 0.6716 0.4429 0.174 Uiso 1 1 calc R . . H13B H 0.4656 0.5937 0.3993 0.174 Uiso 1 1 calc R . . H13C H 0.4178 0.6666 0.4271 0.174 Uiso 1 1 calc R . . O2 O 0.18541(12) 0.29026(11) 0.47463(19) 0.0827(6) Uani 1 1 d . . . N3 N 0.21719(14) 0.25116(13) 0.7063(2) 0.0656(6) Uani 1 1 d D . . H3' H 0.2038(15) 0.2451(15) 0.784(2) 0.079 Uiso 1 1 d D . . N4 N 0.10634(14) 0.33220(13) 0.6099(2) 0.0683(6) Uani 1 1 d . . . C14 C 0.28364(16) 0.20171(16) 0.7038(3) 0.0605(7) Uani 1 1 d . . . C15 C 0.33851(18) 0.21729(18) 0.6262(3) 0.0832(9) Uani 1 1 d . . . H15A H 0.3323 0.2615 0.5701 0.100 Uiso 1 1 calc R . . C16 C 0.4020(2) 0.1677(2) 0.6319(4) 0.0986(11) Uani 1 1 d . . . H16A H 0.4387 0.1786 0.5790 0.118 Uiso 1 1 calc R . . C17 C 0.4130(2) 0.1025(2) 0.7130(4) 0.1018(11) Uani 1 1 d . . . H17A H 0.4562 0.0689 0.7147 0.122 Uiso 1 1 calc R . . C18 C 0.3599(2) 0.08760(18) 0.7914(4) 0.0925(10) Uani 1 1 d . . . H18A H 0.3675 0.0439 0.8488 0.111 Uiso 1 1 calc R . . C19 C 0.29477(17) 0.13665(17) 0.7867(3) 0.0746(8) Uani 1 1 d . . . H19A H 0.2584 0.1255 0.8400 0.090 Uiso 1 1 calc R . . C20 C 0.17074(17) 0.29122(15) 0.5911(3) 0.0625(7) Uani 1 1 d . . . C21 C 0.08728(17) 0.34082(16) 0.7462(3) 0.0764(8) Uani 1 1 d . . . H21A H 0.0946 0.2917 0.7955 0.092 Uiso 1 1 calc R . . H21B H 0.0297 0.3557 0.7275 0.092 Uiso 1 1 calc R . . C22 C 0.1408(2) 0.39949(19) 0.8418(4) 0.1014(11) Uani 1 1 d . . . H22A H 0.1410 0.4462 0.7873 0.122 Uiso 1 1 calc R . . H22B H 0.1971 0.3804 0.8744 0.122 Uiso 1 1 calc R . . C23 C 0.1106(2) 0.4182(2) 0.9726(4) 0.1431(17) Uani 1 1 d . . . H23A H 0.1463 0.4561 1.0308 0.215 Uiso 1 1 calc R . . H23B H 0.1116 0.3723 1.0282 0.215 Uiso 1 1 calc R . . H23C H 0.0551 0.4377 0.9408 0.215 Uiso 1 1 calc R . . C24 C 0.05556(19) 0.37637(16) 0.4889(3) 0.0812(9) Uani 1 1 d . . . H24A H 0.0877 0.3866 0.4225 0.097 Uiso 1 1 calc R . . H24B H 0.0422 0.4254 0.5241 0.097 Uiso 1 1 calc R . . C25 C -0.02373(18) 0.33707(17) 0.4083(3) 0.0895(10) Uani 1 1 d . . . H25A H -0.0582 0.3304 0.4722 0.107 Uiso 1 1 calc R . . H25B H -0.0110 0.2864 0.3786 0.107 Uiso 1 1 calc R . . C26 C -0.0712(2) 0.3818(2) 0.2777(4) 0.1403(16) Uani 1 1 d . . . H26A H -0.1215 0.3550 0.2308 0.210 Uiso 1 1 calc R . . H26B H -0.0382 0.3869 0.2126 0.210 Uiso 1 1 calc R . . H26C H -0.0843 0.4319 0.3066 0.210 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 O1 0.0985(14) 0.0728(12) 0.0411(11) -0.0019(9) 0.0238(10) 0.0030(10) N1 0.0811(16) 0.0610(14) 0.0377(11) 0.0042(11) 0.0136(12) 0.0138(12) N2 0.0715(15) 0.0643(14) 0.0488(13) -0.0001(11) 0.0162(12) 0.0106(12) C1 0.0657(17) 0.0648(17) 0.0407(15) 0.0109(14) 0.0185(14) 0.0033(14) C2 0.0701(19) 0.083(2) 0.0598(19) -0.0002(16) 0.0166(16) 0.0024(16) C3 0.072(2) 0.120(3) 0.059(2) 0.028(2) 0.0080(16) 0.019(2) C4 0.118(3) 0.082(2) 0.089(3) 0.026(2) 0.038(2) 0.030(2) C5 0.144(3) 0.072(2) 0.070(2) 0.0133(18) 0.022(2) 0.021(2) C6 0.109(2) 0.0625(19) 0.0551(18) 0.0058(15) 0.0122(17) 0.0107(17) C7 0.0625(17) 0.0560(16) 0.0486(17) 0.0005(14) 0.0171(14) -0.0035(13) C8 0.0658(18) 0.0743(19) 0.0695(19) -0.0064(15) 0.0222(16) 0.0093(15) C9 0.079(2) 0.0686(19) 0.076(2) -0.0007(15) 0.0178(16) 0.0069(16) C10 0.124(3) 0.087(2) 0.113(3) -0.028(2) 0.027(2) 0.022(2) C11 0.080(2) 0.0711(18) 0.0566(18) 0.0060(14) 0.0185(16) 0.0126(15) C12 0.074(2) 0.102(2) 0.078(2) -0.0062(19) 0.0117(18) 0.0108(18) C13 0.123(3) 0.139(3) 0.065(2) 0.008(2) -0.006(2) 0.024(2) O2 0.0927(14) 0.1162(16) 0.0493(12) 0.0004(10) 0.0365(11) -0.0007(11) N3 0.0756(16) 0.0841(16) 0.0453(14) 0.0020(13) 0.0304(13) 0.0098(13) N4 0.0734(16) 0.0834(16) 0.0513(14) 0.0044(12) 0.0232(13) 0.0069(13) C14 0.0585(17) 0.0718(19) 0.0541(17) -0.0172(14) 0.0211(14) -0.0009(14) C15 0.074(2) 0.099(2) 0.087(2) -0.0120(17) 0.0400(19) -0.0051(18) C16 0.075(2) 0.118(3) 0.118(3) -0.021(2) 0.053(2) -0.003(2) C17 0.070(2) 0.116(3) 0.122(3) -0.036(2) 0.033(2) 0.009(2) C18 0.092(2) 0.088(2) 0.096(3) -0.0133(19) 0.024(2) 0.017(2) C19 0.078(2) 0.081(2) 0.070(2) -0.0102(17) 0.0291(17) 0.0030(17) C20 0.0654(18) 0.0748(18) 0.0535(18) -0.0077(15) 0.0273(16) -0.0075(15) C21 0.0745(19) 0.089(2) 0.0709(19) -0.0070(16) 0.0286(17) 0.0112(16) C22 0.107(3) 0.091(2) 0.101(3) -0.029(2) 0.021(2) 0.0022(19) C23 0.149(4) 0.175(4) 0.093(3) -0.056(3) 0.016(3) 0.057(3) C24 0.093(2) 0.0707(19) 0.080(2) 0.0102(17) 0.0254(19) 0.0023(17) C25 0.081(2) 0.082(2) 0.098(3) 0.0045(18) 0.014(2) 0.0007(18) C26 0.118(3) 0.147(3) 0.124(3) 0.049(3) -0.017(3) 0.002(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 O1 C7 1.231(3) . ? N1 C7 1.366(3) . ? N1 C1 1.411(3) . ? N1 H1' 0.886(16) . ? N2 C7 1.354(3) . ? N2 C8 1.462(3) . ? N2 C11 1.465(3) . ? C1 C6 1.368(3) . ? C1 C2 1.376(3) . ? C2 C3 1.397(4) . ? C2 H2A 0.9300 . ? C3 C4 1.362(4) . ? C3 H3A 0.9300 . ? C4 C5 1.348(4) . ? C4 H4A 0.9300 . ? C5 C6 1.366(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C8 C9 1.502(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.515(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.504(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.527(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? O2 C20 1.225(3) . ? N3 C20 1.359(3) . ? N3 C14 1.418(3) . ? N3 H3' 0.853(16) . ? N4 C20 1.355(3) . ? N4 C21 1.457(3) . ? N4 C24 1.459(3) . ? C14 C19 1.370(4) . ? C14 C15 1.377(4) . ? C15 C16 1.364(4) . ? C15 H15A 0.9300 . ? C16 C17 1.362(4) . ? C16 H16A 0.9300 . ? C17 C18 1.356(4) . ? C17 H17A 0.9300 . ? C18 C19 1.382(4) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? C21 C22 1.495(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.533(4) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 C25 1.506(4) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.507(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 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 C7 N1 C1 124.4(2) . . ? C7 N1 H1' 115.3(17) . . ? C1 N1 H1' 116.8(16) . . ? C7 N2 C8 117.7(2) . . ? C7 N2 C11 125.7(2) . . ? C8 N2 C11 116.6(2) . . ? C6 C1 C2 118.7(2) . . ? C6 C1 N1 118.3(2) . . ? C2 C1 N1 123.0(2) . . ? C1 C2 C3 119.4(3) . . ? C1 C2 H2A 120.3 . . ? C3 C2 H2A 120.3 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3A 119.8 . . ? C2 C3 H3A 119.8 . . ? C5 C4 C3 119.6(3) . . ? C5 C4 H4A 120.2 . . ? C3 C4 H4A 120.2 . . ? C4 C5 C6 120.8(3) . . ? C4 C5 H5A 119.6 . . ? C6 C5 H5A 119.6 . . ? C5 C6 C1 121.0(3) . . ? C5 C6 H6A 119.5 . . ? C1 C6 H6A 119.5 . . ? O1 C7 N2 121.2(2) . . ? O1 C7 N1 121.7(2) . . ? N2 C7 N1 117.1(2) . . ? N2 C8 C9 113.2(2) . . ? N2 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? N2 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C8 C9 C10 112.5(2) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C12 112.7(2) . . ? N2 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? N2 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C11 C12 C13 111.4(3) . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? 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 . . ? C20 N3 C14 124.7(2) . . ? C20 N3 H3' 123.6(18) . . ? C14 N3 H3' 110.6(18) . . ? C20 N4 C21 124.8(2) . . ? C20 N4 C24 118.5(2) . . ? C21 N4 C24 116.5(2) . . ? C19 C14 C15 118.9(3) . . ? C19 C14 N3 117.8(2) . . ? C15 C14 N3 123.2(3) . . ? C16 C15 C14 119.7(3) . . ? C16 C15 H15A 120.1 . . ? C14 C15 H15A 120.1 . . ? C17 C16 C15 121.7(3) . . ? C17 C16 H16A 119.2 . . ? C15 C16 H16A 119.2 . . ? C18 C17 C16 118.8(3) . . ? C18 C17 H17A 120.6 . . ? C16 C17 H17A 120.6 . . ? C17 C18 C19 120.7(3) . . ? C17 C18 H18A 119.7 . . ? C19 C18 H18A 119.7 . . ? C14 C19 C18 120.2(3) . . ? C14 C19 H19A 119.9 . . ? C18 C19 H19A 119.9 . . ? O2 C20 N4 120.9(3) . . ? O2 C20 N3 122.1(3) . . ? N4 C20 N3 117.0(2) . . ? N4 C21 C22 112.5(2) . . ? N4 C21 H21A 109.1 . . ? C22 C21 H21A 109.1 . . ? N4 C21 H21B 109.1 . . ? C22 C21 H21B 109.1 . . ? H21A C21 H21B 107.8 . . ? C21 C22 C23 112.0(3) . . ? C21 C22 H22A 109.2 . . ? C23 C22 H22A 109.2 . . ? C21 C22 H22B 109.2 . . ? C23 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? 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 . . ? N4 C24 C25 114.1(2) . . ? N4 C24 H24A 108.7 . . ? C25 C24 H24A 108.7 . . ? N4 C24 H24B 108.7 . . ? C25 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? C24 C25 C26 112.4(3) . . ? C24 C25 H25A 109.1 . . ? C26 C25 H25A 109.1 . . ? C24 C25 H25B 109.1 . . ? C26 C25 H25B 109.1 . . ? H25A C25 H25B 107.9 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.166 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.030 #======================================END