Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'N.Boubals' 'M.G.B.Drew' 'C.Hill' 'M.J.Hudson' 'P.B.Iveson' 'C.Madic' 'M.L.Russell' 'T.G.A.Youngs' _publ_contact_author_name 'Dr M Drew' _publ_contact_author_address ; Dr M Drew Department of CHemistry Reading University Whiteknights Reading RG6 6AD UNITED KINGDOM ; _publ_contact_author_email 'M.G.B.DREW@READING.AC.UK' _publ_section_title ; Americium(III) and Europium(III) Solvent Extraction Studies of Amide-substituted Triazine Ligands and Complexes formed with Ytterbium(III) ; _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands Walker, N. and Stuart, D., Acta Crystl 1983 A39 158. ; data_1 _database_code_CSD 172878 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 Cl2 N6 O2.50' _chemical_formula_weight 368.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.158(12) _cell_length_b 13.890(15) _cell_length_c 14.249(15) _cell_angle_alpha 69.196(10) _cell_angle_beta 67.614(10) _cell_angle_gamma 71.601(10) _cell_volume 1699(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used all _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 0.404 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5890 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 26.01 _reflns_number_total 5890 _reflns_number_gt 4367 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.0792P)^2^+0.6549P] 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 0.0125(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5890 _refine_ls_number_parameters 457 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1419 _refine_ls_wR_factor_gt 0.1284 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.35771(7) 0.56333(6) 0.22100(6) 0.0555(2) Uani 1 d . . . Cl2 Cl 0.16981(7) 0.63128(6) -0.29387(5) 0.0499(2) Uani 1 d . . . Cl3 Cl -0.51383(8) 1.00448(7) 0.18581(6) 0.0625(2) Uani 1 d . . . Cl4 Cl -0.21478(8) 0.83059(7) 0.50598(6) 0.0603(2) Uani 1 d . . . N21A N -0.2562(2) 0.64325(17) 0.13370(16) 0.0389(5) Uani 1 d . . . C22A C -0.1871(3) 0.62754(19) 0.20333(18) 0.0355(5) Uani 1 d . . . N23A N -0.0459(2) 0.61426(17) 0.18496(15) 0.0373(5) Uani 1 d . . . C24A C 0.0368(3) 0.61362(19) 0.08413(18) 0.0354(5) Uani 1 d . . . N25A N -0.0199(2) 0.62644(16) 0.00680(15) 0.0370(5) Uani 1 d . . . C26A C -0.1637(3) 0.64030(19) 0.03794(18) 0.0350(5) Uani 1 d . . . N31A N -0.2185(2) 0.60848(17) 0.38601(15) 0.0405(5) Uani 1 d . . . H31A H -0.1254 0.6003 0.3669 0.049 Uiso 1 calc R . . C32A C -0.2827(3) 0.6249(2) 0.31296(19) 0.0373(5) Uani 1 d . . . C33A C -0.4313(3) 0.6377(2) 0.3426(2) 0.0473(6) Uani 1 d . . . H33A H -0.4774 0.6484 0.2934 0.057 Uiso 1 calc R . . C34A C -0.5117(3) 0.6344(2) 0.4466(2) 0.0529(7) Uani 1 d . . . H34A H -0.6125 0.6434 0.4675 0.063 Uiso 1 calc R . . C35A C -0.4424(3) 0.6179(2) 0.5195(2) 0.0551(7) Uani 1 d . . . H35A H -0.4957 0.6160 0.5894 0.066 Uiso 1 calc R . . C36A C -0.2937(3) 0.6044(2) 0.4870(2) 0.0504(7) Uani 1 d . . . H36A H -0.2452 0.5923 0.5351 0.060 Uiso 1 calc R . . N11A N -0.1446(2) 0.65625(17) -0.14184(16) 0.0396(5) Uani 1 d . . . H11A H -0.0525 0.6488 -0.1549 0.048 Uiso 1 calc R . . C12A C -0.2324(3) 0.65540(19) -0.04340(18) 0.0352(5) Uani 1 d . . . C13A C -0.3792(3) 0.6675(2) -0.0221(2) 0.0430(6) Uani 1 d . . . H13A H -0.4414 0.6662 0.0458 0.052 Uiso 1 calc R . . C14A C -0.4345(3) 0.6817(2) -0.1024(2) 0.0523(7) Uani 1 d . . . H14A H -0.5341 0.6909 -0.0888 0.063 Uiso 1 calc R . . C15A C -0.3413(3) 0.6821(2) -0.2023(2) 0.0522(7) Uani 1 d . . . H15A H -0.3773 0.6916 -0.2567 0.063 Uiso 1 calc R . . C16A C -0.1954(3) 0.6683(2) -0.2205(2) 0.0493(7) Uani 1 d . . . H16A H -0.1311 0.6674 -0.2874 0.059 Uiso 1 calc R . . N27A N 0.1786(2) 0.60031(18) 0.05992(17) 0.0442(5) Uani 1 d . . . H20A H 0.2329 0.5999 -0.0033 0.053 Uiso 1 calc R . . H20B H 0.2170 0.5920 0.1073 0.053 Uiso 1 calc R . . N11B N 0.1028(2) 0.89374(17) -0.34307(16) 0.0417(5) Uani 1 d . . . H11B H 0.0098 0.9005 -0.3225 0.050 Uiso 1 calc R . . C12B C 0.1689(3) 0.8821(2) -0.27246(19) 0.0399(6) Uani 1 d . . . C13B C 0.3161(3) 0.8731(2) -0.3045(2) 0.0528(7) Uani 1 d . . . H13B H 0.3632 0.8658 -0.2570 0.063 Uiso 1 calc R . . C14B C 0.3946(3) 0.8749(3) -0.4085(2) 0.0619(8) Uani 1 d . . . H14B H 0.4950 0.8685 -0.4309 0.074 Uiso 1 calc R . . C15B C 0.3247(3) 0.8860(3) -0.4787(2) 0.0601(8) Uani 1 d . . . H15B H 0.3765 0.8872 -0.5486 0.072 Uiso 1 calc R . . C16B C 0.1752(3) 0.8952(2) -0.4426(2) 0.0527(7) Uani 1 d . . . H16B H 0.1256 0.9024 -0.4885 0.063 Uiso 1 calc R . . N21B N 0.1435(2) 0.86654(17) -0.09398(16) 0.0398(5) Uani 1 d . . . C22B C 0.0741(3) 0.88014(19) -0.16266(18) 0.0362(5) Uani 1 d . . . N23B N -0.0674(2) 0.89334(16) -0.14425(15) 0.0372(5) Uani 1 d . . . C24B C -0.1491(3) 0.89406(18) -0.04318(18) 0.0351(5) Uani 1 d . . . N25B N -0.0914(2) 0.88074(16) 0.03352(15) 0.0374(5) Uani 1 d . . . C26B C 0.0523(3) 0.86740(18) 0.00265(18) 0.0353(5) Uani 1 d . . . N27B N -0.2921(2) 0.90812(18) -0.01799(17) 0.0436(5) Uani 1 d . . . H20C H -0.3457 0.9086 0.0454 0.052 Uiso 1 calc R . . H20D H -0.3315 0.9167 -0.0650 0.052 Uiso 1 calc R . . N31B N 0.0303(2) 0.84799(17) 0.18285(16) 0.0398(5) Uani 1 d . . . H31B H -0.0607 0.8517 0.1954 0.048 Uiso 1 calc R . . C32B C 0.1198(3) 0.85337(18) 0.08397(19) 0.0363(5) Uani 1 d . . . C33B C 0.2650(3) 0.8472(2) 0.0628(2) 0.0441(6) Uani 1 d . . . H33B H 0.3280 0.8508 -0.0052 0.053 Uiso 1 calc R . . C34B C 0.3171(3) 0.8357(2) 0.1442(2) 0.0516(7) Uani 1 d . . . H34B H 0.4156 0.8314 0.1307 0.062 Uiso 1 calc R . . C35B C 0.2237(3) 0.8305(2) 0.2442(2) 0.0523(7) Uani 1 d . . . H35B H 0.2580 0.8226 0.2989 0.063 Uiso 1 calc R . . C36B C 0.0780(3) 0.8370(2) 0.2625(2) 0.0490(7) Uani 1 d . . . H36B H 0.0132 0.8339 0.3299 0.059 Uiso 1 calc R . . O100 O 0.6460(2) 0.4006(2) 0.14989(18) 0.0652(6) Uani 1 d D . . H1 H 0.568(4) 0.452(3) 0.172(3) 0.097(5) Uiso 1 d D . . H2 H 0.702(4) 0.392(3) 0.190(3) 0.097(5) Uiso 1 d D . . O101 O -0.8257(2) 1.0732(2) 0.34046(18) 0.0674(7) Uani 1 d D . . H3 H -0.745(4) 1.056(3) 0.294(3) 0.097(5) Uiso 1 d D . . H4 H -0.822(4) 1.109(3) 0.374(3) 0.097(5) Uiso 1 d D . . O102 O 0.0550(3) 0.5802(3) 0.3852(2) 0.0803(9) Uani 1 d D . . H5 H 0.138(4) 0.582(3) 0.335(3) 0.097(5) Uiso 1 d D . . H6 H 0.033(5) 0.529(3) 0.395(4) 0.097(5) Uiso 1 d D . . O103 O -0.2564(2) 0.8609(2) 0.28425(18) 0.0653(6) Uani 1 d D . . H7 H -0.325(4) 0.900(3) 0.263(3) 0.097(5) Uiso 1 d D . . H8 H -0.275(4) 0.863(3) 0.349(3) 0.097(5) Uiso 1 d D . . O104 O 0.0989(3) 0.6937(3) 0.49580(19) 0.0960(10) Uani 1 d D . . H9 H 0.003(4) 0.722(3) 0.508(3) 0.097(5) Uiso 1 d D . . H10 H 0.110(4) 0.668(3) 0.554(3) 0.097(5) Uiso 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0389(4) 0.0753(5) 0.0579(4) -0.0262(4) -0.0163(3) -0.0078(3) Cl2 0.0453(4) 0.0585(4) 0.0457(4) -0.0099(3) -0.0178(3) -0.0102(3) Cl3 0.0416(4) 0.0969(6) 0.0569(4) -0.0346(4) -0.0183(3) -0.0049(4) Cl4 0.0522(4) 0.0823(6) 0.0491(4) -0.0270(4) -0.0166(3) -0.0051(4) N21A 0.0365(11) 0.0469(12) 0.0350(10) -0.0098(9) -0.0133(9) -0.0094(9) C22A 0.0362(13) 0.0385(13) 0.0334(12) -0.0089(10) -0.0126(10) -0.0082(10) N23A 0.0365(11) 0.0437(12) 0.0337(10) -0.0089(9) -0.0136(8) -0.0088(9) C24A 0.0365(13) 0.0355(13) 0.0372(12) -0.0089(10) -0.0134(10) -0.0095(10) N25A 0.0366(11) 0.0426(12) 0.0341(10) -0.0099(9) -0.0116(8) -0.0108(9) C26A 0.0370(13) 0.0359(13) 0.0349(12) -0.0082(10) -0.0134(10) -0.0096(10) N31A 0.0371(11) 0.0497(13) 0.0351(11) -0.0115(10) -0.0115(9) -0.0087(10) C32A 0.0383(13) 0.0407(14) 0.0348(12) -0.0089(10) -0.0130(10) -0.0099(11) C33A 0.0388(14) 0.0612(18) 0.0442(14) -0.0183(13) -0.0124(11) -0.0090(12) C34A 0.0383(14) 0.067(2) 0.0481(15) -0.0203(14) -0.0036(12) -0.0103(13) C35A 0.0557(18) 0.0650(19) 0.0359(13) -0.0175(13) -0.0011(12) -0.0124(15) C36A 0.0557(17) 0.0615(18) 0.0351(13) -0.0135(13) -0.0134(12) -0.0134(14) N11A 0.0375(11) 0.0499(13) 0.0349(10) -0.0080(9) -0.0135(9) -0.0144(9) C12A 0.0374(13) 0.0380(13) 0.0329(12) -0.0099(10) -0.0112(10) -0.0104(10) C13A 0.0390(13) 0.0541(16) 0.0403(13) -0.0165(12) -0.0105(11) -0.0133(12) C14A 0.0396(15) 0.0699(19) 0.0574(16) -0.0216(15) -0.0205(13) -0.0121(13) C15A 0.0565(17) 0.0672(19) 0.0429(14) -0.0120(14) -0.0239(13) -0.0181(14) C16A 0.0535(16) 0.0666(18) 0.0316(12) -0.0103(12) -0.0134(11) -0.0200(14) N27A 0.0350(11) 0.0630(15) 0.0372(11) -0.0123(10) -0.0124(9) -0.0131(10) N11B 0.0455(12) 0.0458(12) 0.0339(10) -0.0124(9) -0.0115(9) -0.0083(10) C12B 0.0424(14) 0.0402(14) 0.0362(12) -0.0120(11) -0.0136(11) -0.0032(11) C13B 0.0428(15) 0.0622(18) 0.0472(15) -0.0124(14) -0.0153(12) -0.0032(13) C14B 0.0452(16) 0.071(2) 0.0522(17) -0.0132(15) -0.0051(13) -0.0056(15) C15B 0.0566(18) 0.066(2) 0.0426(15) -0.0179(14) -0.0025(13) -0.0049(15) C16B 0.0650(19) 0.0579(18) 0.0340(13) -0.0144(13) -0.0126(13) -0.0117(14) N21B 0.0394(11) 0.0471(12) 0.0356(10) -0.0108(9) -0.0146(9) -0.0087(9) C22B 0.0424(14) 0.0336(13) 0.0335(12) -0.0076(10) -0.0142(10) -0.0073(10) N23B 0.0375(11) 0.0409(12) 0.0357(10) -0.0113(9) -0.0145(8) -0.0061(9) C24B 0.0405(13) 0.0330(12) 0.0343(12) -0.0060(10) -0.0152(10) -0.0097(10) N25B 0.0396(11) 0.0403(11) 0.0347(10) -0.0086(9) -0.0151(9) -0.0086(9) C26B 0.0412(13) 0.0319(12) 0.0357(12) -0.0076(10) -0.0156(10) -0.0080(10) N27B 0.0393(12) 0.0594(14) 0.0360(11) -0.0132(10) -0.0130(9) -0.0127(10) N31B 0.0432(11) 0.0452(12) 0.0349(10) -0.0087(9) -0.0166(9) -0.0108(9) C32B 0.0419(13) 0.0339(13) 0.0363(12) -0.0093(10) -0.0176(10) -0.0051(10) C33B 0.0426(14) 0.0497(15) 0.0429(14) -0.0126(12) -0.0151(11) -0.0104(12) C34B 0.0451(15) 0.0610(18) 0.0580(17) -0.0146(14) -0.0264(13) -0.0114(13) C35B 0.0624(18) 0.0577(17) 0.0475(15) -0.0090(13) -0.0319(14) -0.0136(14) C36B 0.0568(17) 0.0571(17) 0.0372(13) -0.0111(13) -0.0216(12) -0.0099(14) O100 0.0426(12) 0.1014(18) 0.0642(14) -0.0438(13) -0.0201(10) -0.0019(11) O101 0.0487(12) 0.114(2) 0.0498(12) -0.0325(13) -0.0143(10) -0.0196(13) O102 0.0452(13) 0.142(3) 0.0559(14) -0.0267(16) -0.0125(10) -0.0257(15) O103 0.0524(13) 0.0905(17) 0.0511(12) -0.0191(12) -0.0210(10) -0.0059(11) O104 0.0609(15) 0.172(3) 0.0491(13) -0.0380(16) -0.0221(12) 0.0007(17) _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 N21A C26A 1.336(3) . ? N21A C22A 1.344(3) . ? C22A N23A 1.319(3) . ? C22A C32A 1.487(4) . ? N23A C24A 1.362(3) . ? C24A N27A 1.313(3) . ? C24A N25A 1.363(3) . ? N25A C26A 1.326(3) . ? C26A C12A 1.492(3) . ? N31A C36A 1.337(4) . ? N31A C32A 1.347(3) . ? C32A C33A 1.373(4) . ? C33A C34A 1.386(4) . ? C34A C35A 1.382(4) . ? C35A C36A 1.372(5) . ? N11A C16A 1.342(3) . ? N11A C12A 1.344(3) . ? C12A C13A 1.370(4) . ? C13A C14A 1.387(4) . ? C14A C15A 1.376(4) . ? C15A C16A 1.366(4) . ? N11B C16B 1.322(4) . ? N11B C12B 1.349(3) . ? C12B C13B 1.365(4) . ? C12B C22B 1.488(4) . ? C13B C14B 1.385(4) . ? C14B C15B 1.375(5) . ? C15B C16B 1.384(5) . ? N21B C26B 1.337(3) . ? N21B C22B 1.342(3) . ? C22B N23B 1.322(4) . ? N23B C24B 1.363(3) . ? C24B N27B 1.324(4) . ? C24B N25B 1.359(3) . ? N25B C26B 1.326(4) . ? C26B C32B 1.487(3) . ? N31B C36B 1.341(3) . ? N31B C32B 1.345(3) . ? C32B C33B 1.369(4) . ? C33B C34B 1.391(4) . ? C34B C35B 1.370(4) . ? C35B C36B 1.380(4) . ? 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 C26A N21A C22A 112.2(2) . . ? N23A C22A N21A 127.3(2) . . ? N23A C22A C32A 117.5(2) . . ? N21A C22A C32A 115.2(2) . . ? C22A N23A C24A 114.9(2) . . ? N27A C24A N25A 118.2(2) . . ? N27A C24A N23A 118.4(2) . . ? N25A C24A N23A 123.4(2) . . ? C26A N25A C24A 114.1(2) . . ? N25A C26A N21A 128.0(2) . . ? N25A C26A C12A 116.7(2) . . ? N21A C26A C12A 115.3(2) . . ? C36A N31A C32A 122.7(2) . . ? N31A C32A C33A 119.2(2) . . ? N31A C32A C22A 117.5(2) . . ? C33A C32A C22A 123.3(2) . . ? C32A C33A C34A 119.3(3) . . ? C35A C34A C33A 120.1(3) . . ? C36A C35A C34A 118.9(3) . . ? N31A C36A C35A 119.9(3) . . ? C16A N11A C12A 122.4(2) . . ? N11A C12A C13A 119.1(2) . . ? N11A C12A C26A 117.7(2) . . ? C13A C12A C26A 123.2(2) . . ? C12A C13A C14A 119.6(2) . . ? C15A C14A C13A 119.7(3) . . ? C16A C15A C14A 119.2(2) . . ? N11A C16A C15A 120.1(2) . . ? C16B N11B C12B 122.6(3) . . ? N11B C12B C13B 119.2(2) . . ? N11B C12B C22B 116.9(2) . . ? C13B C12B C22B 123.9(2) . . ? C12B C13B C14B 119.3(3) . . ? C15B C14B C13B 120.3(3) . . ? C14B C15B C16B 118.3(3) . . ? N11B C16B C15B 120.2(3) . . ? C26B N21B C22B 112.5(2) . . ? N23B C22B N21B 127.7(2) . . ? N23B C22B C12B 117.0(2) . . ? N21B C22B C12B 115.4(2) . . ? C22B N23B C24B 114.4(2) . . ? N27B C24B N25B 118.1(2) . . ? N27B C24B N23B 118.5(2) . . ? N25B C24B N23B 123.4(2) . . ? C26B N25B C24B 114.8(2) . . ? N25B C26B N21B 127.2(2) . . ? N25B C26B C32B 116.5(2) . . ? N21B C26B C32B 116.2(2) . . ? C36B N31B C32B 122.3(2) . . ? N31B C32B C33B 119.6(2) . . ? N31B C32B C26B 116.8(2) . . ? C33B C32B C26B 123.6(2) . . ? C32B C33B C34B 119.2(3) . . ? C35B C34B C33B 120.1(3) . . ? C34B C35B C36B 119.1(2) . . ? N31B C36B C35B 119.8(3) . . ? _refine_diff_density_max 0.260 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.072 _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands ; data_2 _database_code_CSD 172879 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 N6 O' _chemical_formula_weight 360.42 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.946(12) _cell_length_b 17.15(2) _cell_length_c 11.849(14) _cell_angle_alpha 90 _cell_angle_beta 109.118(10) _cell_angle_gamma 90 _cell_volume 1910(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used all _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6387 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 26.08 _reflns_number_total 3383 _reflns_number_gt 1756 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.1872P)^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 SHELXL _refine_ls_extinction_coef 0.005(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3383 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1544 _refine_ls_R_factor_gt 0.0844 _refine_ls_wR_factor_ref 0.2846 _refine_ls_wR_factor_gt 0.2336 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N -0.1515(3) 0.3441(2) 0.1668(3) 0.0716(9) Uani 1 d . . . C12 C -0.2615(4) 0.3914(3) 0.1162(4) 0.0855(13) Uani 1 d . . . H12 H -0.2622 0.4192 0.0487 0.103 Uiso 1 calc R . . C13 C -0.3732(5) 0.4013(3) 0.1582(4) 0.0878(13) Uani 1 d . . . H13 H -0.4472 0.4354 0.1210 0.105 Uiso 1 calc R . . C14 C -0.3728(4) 0.3599(3) 0.2558(4) 0.0906(14) Uani 1 d . . . H14 H -0.4486 0.3644 0.2850 0.109 Uiso 1 calc R . . C15 C -0.2605(4) 0.3112(2) 0.3118(3) 0.0748(11) Uani 1 d . . . H15 H -0.2581 0.2838 0.3801 0.090 Uiso 1 calc R . . C16 C -0.1523(3) 0.3040(2) 0.2645(3) 0.0551(8) Uani 1 d . . . C22 C -0.0283(3) 0.25195(19) 0.3202(3) 0.0545(8) Uani 1 d . . . N21 N 0.0734(3) 0.24718(17) 0.2682(2) 0.0578(8) Uani 1 d . . . C26 C 0.1791(3) 0.19742(19) 0.3217(3) 0.0535(8) Uani 1 d . . . N23 N 0.1912(3) 0.15642(16) 0.4207(2) 0.0575(8) Uani 1 d . . . C24 C 0.0850(4) 0.1668(2) 0.4655(3) 0.0576(9) Uani 1 d . . . N25 N -0.0277(3) 0.21353(17) 0.4169(2) 0.0597(8) Uani 1 d . . . C32 C 0.2952(4) 0.1852(2) 0.2709(3) 0.0584(9) Uani 1 d . . . N31 N 0.2912(3) 0.2268(2) 0.1742(3) 0.0775(10) Uani 1 d . . . C36 C 0.3965(5) 0.2147(3) 0.1296(4) 0.0880(14) Uani 1 d . . . H36 H 0.3958 0.2436 0.0631 0.106 Uiso 1 calc R . . C35 C 0.5057(4) 0.1627(3) 0.1751(4) 0.0846(13) Uani 1 d . . . H35 H 0.5758 0.1562 0.1398 0.102 Uiso 1 calc R . . C34 C 0.5082(5) 0.1212(3) 0.2726(4) 0.0873(14) Uani 1 d . . . H34 H 0.5810 0.0857 0.3064 0.105 Uiso 1 calc R . . C33 C 0.4005(4) 0.1321(3) 0.3216(3) 0.0783(12) Uani 1 d . . . H33 H 0.3999 0.1036 0.3881 0.094 Uiso 1 calc R . . N41 N 0.0859(3) 0.12836(17) 0.5670(2) 0.0594(8) Uani 1 d . . . H41 H 0.0139 0.1371 0.5903 0.071 Uiso 1 calc R . . C42 C 0.1864(4) 0.0776(2) 0.6371(3) 0.0634(10) Uani 1 d . . . O43 O 0.2837(3) 0.05035(19) 0.6096(3) 0.0971(11) Uani 1 d . . . C51 C 0.1585(4) 0.0553(2) 0.7512(3) 0.0590(9) Uani 1 d . . . H51 H 0.0989 0.0961 0.7685 0.071 Uiso 1 calc R . . C52 C 0.2945(4) 0.0506(3) 0.8568(3) 0.0896(14) Uani 1 d . . . H52A H 0.3413 0.1010 0.8701 0.108 Uiso 1 calc R . . H52B H 0.3586 0.0131 0.8400 0.108 Uiso 1 calc R . . C53 C 0.2610(5) 0.0257(4) 0.9694(4) 0.119(2) Uani 1 d . . . H53A H 0.3494 0.0177 1.0343 0.143 Uiso 1 calc R . . H53B H 0.2091 0.0672 0.9927 0.143 Uiso 1 calc R . . C54 C 0.1741(7) -0.0482(3) 0.9497(5) 0.1130(19) Uani 1 d . . . H54A H 0.2313 -0.0913 0.9381 0.136 Uiso 1 calc R . . H54B H 0.1483 -0.0591 1.0203 0.136 Uiso 1 calc R . . C55 C 0.0419(7) -0.0424(3) 0.8438(5) 0.1158(19) Uani 1 d . . . H55A H -0.0210 -0.0036 0.8593 0.139 Uiso 1 calc R . . H55B H -0.0073 -0.0921 0.8308 0.139 Uiso 1 calc R . . C56 C 0.0763(5) -0.0200(3) 0.7329(4) 0.0957(15) Uani 1 d . . . H56A H 0.1318 -0.0611 0.7132 0.115 Uiso 1 calc R . . H56B H -0.0114 -0.0144 0.6664 0.115 Uiso 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 N11 0.0567(19) 0.094(2) 0.0621(18) 0.0099(15) 0.0169(14) 0.0102(17) C12 0.064(3) 0.106(4) 0.081(3) 0.019(2) 0.016(2) 0.016(2) C13 0.067(3) 0.099(3) 0.091(3) 0.003(2) 0.017(2) 0.025(2) C14 0.066(3) 0.110(4) 0.103(3) -0.013(3) 0.038(2) 0.015(3) C15 0.074(3) 0.081(3) 0.076(2) -0.004(2) 0.034(2) 0.011(2) C16 0.054(2) 0.056(2) 0.0547(18) -0.0067(15) 0.0163(14) 0.0011(16) C22 0.056(2) 0.0550(19) 0.0577(19) -0.0119(15) 0.0251(15) -0.0081(16) N21 0.0608(18) 0.0612(17) 0.0565(15) -0.0012(13) 0.0261(13) 0.0038(15) C26 0.058(2) 0.0525(19) 0.0515(17) -0.0058(14) 0.0194(14) -0.0030(16) N23 0.0606(18) 0.0602(18) 0.0535(16) -0.0022(12) 0.0213(13) 0.0027(14) C24 0.060(2) 0.062(2) 0.0539(19) -0.0046(15) 0.0223(16) -0.0028(17) N25 0.0637(19) 0.0628(18) 0.0577(16) -0.0045(13) 0.0270(13) -0.0035(15) C32 0.058(2) 0.061(2) 0.0587(18) 0.0013(15) 0.0229(15) 0.0016(17) N31 0.074(2) 0.090(2) 0.080(2) 0.0227(17) 0.0407(17) 0.0214(18) C36 0.085(3) 0.110(4) 0.089(3) 0.034(2) 0.055(2) 0.026(3) C35 0.078(3) 0.103(3) 0.088(3) 0.012(2) 0.048(2) 0.021(3) C34 0.081(3) 0.101(3) 0.088(3) 0.018(2) 0.040(2) 0.038(2) C33 0.084(3) 0.095(3) 0.064(2) 0.022(2) 0.035(2) 0.027(2) N41 0.0605(18) 0.0666(19) 0.0562(16) 0.0019(13) 0.0263(13) -0.0007(14) C42 0.066(2) 0.063(2) 0.066(2) 0.0002(16) 0.0287(18) 0.0005(19) O43 0.100(2) 0.116(3) 0.095(2) 0.0321(17) 0.0597(18) 0.0394(19) C51 0.062(2) 0.064(2) 0.0562(19) -0.0014(15) 0.0265(15) 0.0005(17) C52 0.078(3) 0.127(4) 0.062(2) -0.004(2) 0.021(2) -0.006(3) C53 0.105(4) 0.185(7) 0.060(3) 0.002(3) 0.015(2) 0.000(4) C54 0.161(5) 0.107(4) 0.096(4) 0.032(3) 0.076(4) 0.031(4) C55 0.163(5) 0.104(4) 0.101(4) -0.013(3) 0.072(4) -0.058(4) C56 0.128(4) 0.091(3) 0.076(3) -0.018(2) 0.044(3) -0.042(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 N11 C12 1.337(5) . ? N11 C16 1.350(4) . ? C12 C13 1.369(6) . ? C13 C14 1.356(6) . ? C14 C15 1.380(6) . ? C15 C16 1.371(5) . ? C16 C22 1.492(5) . ? C22 N25 1.321(4) . ? C22 N21 1.347(4) . ? N21 C26 1.342(4) . ? C26 N23 1.339(4) . ? C26 C32 1.482(5) . ? N23 C24 1.340(4) . ? C24 N25 1.345(4) . ? C24 N41 1.369(4) . ? C32 N31 1.340(4) . ? C32 C33 1.370(5) . ? N31 C36 1.335(5) . ? C36 C35 1.372(6) . ? C35 C34 1.352(6) . ? C34 C33 1.387(5) . ? N41 C42 1.380(5) . ? C42 O43 1.211(4) . ? C42 C51 1.516(5) . ? C51 C56 1.506(5) . ? C51 C52 1.514(5) . ? C52 C53 1.539(6) . ? C53 C54 1.508(8) . ? C54 C55 1.494(8) . ? C55 C56 1.513(6) . ? 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 C12 N11 C16 117.4(3) . . ? N11 C12 C13 123.7(4) . . ? C14 C13 C12 118.0(4) . . ? C13 C14 C15 120.3(4) . . ? C16 C15 C14 118.5(4) . . ? N11 C16 C15 122.1(3) . . ? N11 C16 C22 116.6(3) . . ? C15 C16 C22 121.3(3) . . ? N25 C22 N21 125.1(3) . . ? N25 C22 C16 116.8(3) . . ? N21 C22 C16 118.0(3) . . ? C26 N21 C22 114.3(3) . . ? N23 C26 N21 125.5(3) . . ? N23 C26 C32 115.1(3) . . ? N21 C26 C32 119.5(3) . . ? C26 N23 C24 114.9(3) . . ? N23 C24 N25 124.2(3) . . ? N23 C24 N41 120.4(3) . . ? N25 C24 N41 115.4(3) . . ? C22 N25 C24 115.9(3) . . ? N31 C32 C33 122.3(3) . . ? N31 C32 C26 117.6(3) . . ? C33 C32 C26 120.1(3) . . ? C36 N31 C32 116.6(3) . . ? N31 C36 C35 124.6(4) . . ? C34 C35 C36 118.0(3) . . ? C35 C34 C33 119.1(4) . . ? C32 C33 C34 119.4(4) . . ? C24 N41 C42 128.9(3) . . ? O43 C42 N41 124.5(3) . . ? O43 C42 C51 122.5(3) . . ? N41 C42 C51 112.9(3) . . ? C56 C51 C52 111.6(4) . . ? C56 C51 C42 109.8(3) . . ? C52 C51 C42 112.1(3) . . ? C51 C52 C53 110.1(4) . . ? C54 C53 C52 112.1(4) . . ? C55 C54 C53 112.0(4) . . ? C54 C55 C56 111.1(5) . . ? C51 C56 C55 111.1(3) . . ? _refine_diff_density_max 0.360 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.053 _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands ; data_3 _database_code_CSD 172880 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H29 N6 O3' _chemical_formula_weight 425.51 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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 12.458(14) _cell_length_b 14.997(17) _cell_length_c 12.515(14) _cell_angle_alpha 90.00 _cell_angle_beta 93.540(10) _cell_angle_gamma 90.00 _cell_volume 2334(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used all _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 908 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7430 _diffrn_reflns_av_R_equivalents 0.0761 _diffrn_reflns_av_sigmaI/netI 0.1043 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.10 _reflns_number_total 4416 _reflns_number_gt 1676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.1804P)^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 SHELXL _refine_ls_extinction_coef 0.004(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4416 _refine_ls_number_parameters 297 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.2214 _refine_ls_R_factor_gt 0.0920 _refine_ls_wR_factor_ref 0.3061 _refine_ls_wR_factor_gt 0.2439 _refine_ls_goodness_of_fit_ref 0.914 _refine_ls_restrained_S_all 0.914 _refine_ls_shift/su_max 0.212 _refine_ls_shift/su_mean 0.010 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N11 N 1.2338(3) 0.1856(2) 0.3241(3) 0.0594(10) Uani 1 d . . . C12 C 1.1484(3) 0.2398(3) 0.3164(3) 0.0512(10) Uani 1 d . . . C13 C 1.0991(4) 0.2650(3) 0.2194(4) 0.0653(12) Uani 1 d . . . H13 H 1.0401 0.3031 0.2167 0.078 Uiso 1 calc R . . C14 C 1.1389(4) 0.2327(4) 0.1257(4) 0.0766(14) Uani 1 d . . . H14 H 1.1061 0.2480 0.0595 0.092 Uiso 1 calc R . . C15 C 1.2272(4) 0.1779(3) 0.1320(4) 0.0738(14) Uani 1 d . . . H15 H 1.2565 0.1563 0.0706 0.089 Uiso 1 calc R . . C16 C 1.2706(4) 0.1563(3) 0.2309(4) 0.0720(14) Uani 1 d . . . H16 H 1.3299 0.1185 0.2348 0.086 Uiso 1 calc R . . N23 N 1.0106(3) 0.3129(2) 0.4118(3) 0.0510(9) Uani 1 d . . . C22 C 1.1090(3) 0.2751(3) 0.4190(3) 0.0490(10) Uani 1 d . . . N21 N 1.1733(3) 0.2706(2) 0.5078(3) 0.0540(9) Uani 1 d . . . C26 C 1.1354(3) 0.3095(3) 0.5942(3) 0.0501(11) Uani 1 d . . . N25 N 1.0397(3) 0.3511(2) 0.5958(3) 0.0560(10) Uani 1 d . . . C24 C 0.9818(3) 0.3504(2) 0.5022(3) 0.0476(10) Uani 1 d . . . N31 N 1.1725(3) 0.3481(3) 0.7815(3) 0.0682(11) Uani 1 d . . . C32 C 1.2048(3) 0.3040(3) 0.6951(4) 0.0568(11) Uani 1 d . . . C33 C 1.2990(4) 0.2548(3) 0.7003(4) 0.0596(12) Uani 1 d . . . H33 H 1.3206 0.2260 0.6394 0.072 Uiso 1 calc R . . C34 C 1.3611(4) 0.2480(3) 0.7950(4) 0.0725(13) Uani 1 d . . . H34 H 1.4255 0.2164 0.7982 0.087 Uiso 1 calc R . . C35 C 1.3261(4) 0.2887(4) 0.8839(4) 0.0808(15) Uani 1 d . . . H35 H 1.3633 0.2826 0.9502 0.097 Uiso 1 calc R . . C36 C 1.2336(4) 0.3394(4) 0.8721(5) 0.0815(15) Uani 1 d . . . H36 H 1.2123 0.3698 0.9320 0.098 Uiso 1 calc R . . N41 N 0.8794(3) 0.3883(2) 0.4954(3) 0.0549(9) Uani 1 d . . . H41 H 0.8327 0.3641 0.4510 0.066 Uiso 1 calc R . . C42 C 0.8454(4) 0.4606(3) 0.5524(4) 0.0586(12) Uani 1 d . . . O43 O 0.9019(3) 0.4995(2) 0.6192(3) 0.0766(11) Uani 1 d . . . C44 C 0.7302(4) 0.4918(3) 0.5182(4) 0.0675(13) Uani 1 d . . . H44A H 0.7330 0.5336 0.4592 0.081 Uiso 1 calc R . . H44B H 0.6877 0.4409 0.4932 0.081 Uiso 1 calc R . . C45 C 0.6757(4) 0.5366(3) 0.6109(4) 0.0697(14) Uani 1 d . . . H45 H 0.7306 0.5736 0.6489 0.084 Uiso 1 calc R . . C46 C 0.5891(4) 0.5995(4) 0.5658(5) 0.0937(19) Uani 1 d . . . H46A H 0.6178 0.6363 0.5116 0.112 Uiso 1 calc R . . H46B H 0.5650 0.6365 0.6221 0.112 Uiso 1 calc R . . H46C H 0.5296 0.5655 0.5350 0.112 Uiso 1 calc R . . C47 C 0.6435(4) 0.4659(3) 0.6893(4) 0.0721(14) Uani 1 d . . . H47A H 0.7052 0.4272 0.7023 0.087 Uiso 1 calc R . . H47B H 0.5877 0.4303 0.6525 0.087 Uiso 1 calc R . . C48 C 0.6035(5) 0.4895(4) 0.7980(5) 0.0913(19) Uani 1 d . . . C49 C 0.4755(7) 0.5068(6) 0.7765(9) 0.155(4) Uani 1 d . . . H49A H 0.4437 0.4577 0.7368 0.186 Uiso 1 calc R . . H49B H 0.4641 0.5609 0.7364 0.186 Uiso 1 calc R . . H49C H 0.4429 0.5120 0.8438 0.186 Uiso 1 calc R . . C50 C 0.6015(6) 0.4088(5) 0.8660(6) 0.127(2) Uani 1 d . . . H50A H 0.5770 0.3589 0.8231 0.152 Uiso 1 calc R . . H50B H 0.5535 0.4183 0.9221 0.152 Uiso 1 calc R . . H50C H 0.6725 0.3970 0.8968 0.152 Uiso 1 calc R . . C51 C 0.6405(11) 0.5719(7) 0.8435(7) 0.230(7) Uani 1 d . . . H51A H 0.6387 0.6170 0.7889 0.276 Uiso 1 calc R . . H51B H 0.7128 0.5649 0.8733 0.276 Uiso 1 calc R . . H51C H 0.5948 0.5893 0.8989 0.276 Uiso 1 calc R . . O100 O 1.5446(5) -0.1128(3) -0.0129(4) 0.1222(17) Uani 1 d D . . H1 H 1.579(6) -0.078(4) -0.045(6) 0.147 Uiso 1 d D . . H2 H 1.502(5) -0.086(5) 0.022(6) 0.147 Uiso 1 d D . . O200 O 1.5172(4) 0.0208(3) -0.1846(3) 0.0921(12) Uani 1 d D . . H4 H 1.519(5) -0.007(4) -0.131(3) 0.111 Uiso 1 d D . . H3 H 1.478(4) 0.015(4) -0.239(3) 0.111 Uiso 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N11 0.058(2) 0.067(2) 0.052(2) -0.0081(18) -0.0002(18) 0.0035(18) C12 0.052(2) 0.054(2) 0.048(3) -0.0021(19) -0.003(2) -0.0003(19) C13 0.063(3) 0.079(3) 0.054(3) 0.000(2) -0.003(2) 0.009(2) C14 0.081(3) 0.096(4) 0.052(3) -0.001(3) -0.006(3) 0.002(3) C15 0.068(3) 0.099(4) 0.054(3) -0.012(3) 0.007(3) 0.003(3) C16 0.068(3) 0.085(3) 0.063(4) -0.007(3) 0.006(3) 0.016(3) N23 0.0468(19) 0.055(2) 0.051(2) -0.0011(16) -0.0007(16) -0.0032(15) C22 0.048(2) 0.048(2) 0.051(3) -0.0018(18) 0.000(2) -0.0041(18) N21 0.0503(19) 0.062(2) 0.049(2) -0.0062(17) 0.0009(18) -0.0010(16) C26 0.048(2) 0.052(2) 0.049(3) -0.0059(19) 0.000(2) -0.0105(19) N25 0.050(2) 0.058(2) 0.060(3) -0.0006(17) 0.0017(19) 0.0030(17) C24 0.045(2) 0.049(2) 0.048(3) 0.0018(19) -0.005(2) -0.0049(18) N31 0.064(2) 0.087(3) 0.053(3) -0.010(2) -0.006(2) 0.007(2) C32 0.056(3) 0.057(2) 0.057(3) -0.005(2) 0.001(2) -0.006(2) C33 0.062(3) 0.065(3) 0.050(3) -0.004(2) -0.006(2) 0.007(2) C34 0.069(3) 0.087(3) 0.059(3) 0.002(3) -0.011(3) 0.002(3) C35 0.078(3) 0.105(4) 0.057(3) 0.002(3) -0.017(3) 0.006(3) C36 0.086(4) 0.094(4) 0.063(4) -0.012(3) -0.004(3) 0.003(3) N41 0.0420(19) 0.062(2) 0.061(2) -0.0091(17) 0.0006(17) -0.0041(16) C42 0.061(3) 0.055(3) 0.060(3) 0.001(2) 0.005(2) -0.003(2) O43 0.066(2) 0.068(2) 0.093(3) -0.0212(18) -0.0159(19) -0.0024(16) C44 0.068(3) 0.068(3) 0.065(3) -0.001(2) 0.003(3) 0.014(2) C45 0.071(3) 0.064(3) 0.075(4) -0.001(2) 0.004(3) 0.019(2) C46 0.085(4) 0.077(3) 0.121(5) 0.015(3) 0.017(4) 0.023(3) C47 0.069(3) 0.070(3) 0.077(4) -0.006(3) -0.002(3) 0.000(3) C48 0.106(5) 0.089(4) 0.081(4) 0.005(3) 0.022(4) 0.029(3) C49 0.124(6) 0.163(7) 0.184(10) 0.013(6) 0.057(6) 0.043(5) C50 0.131(6) 0.163(7) 0.087(5) 0.019(5) 0.015(5) -0.004(5) C51 0.41(2) 0.193(9) 0.094(7) -0.073(7) 0.070(10) -0.115(11) O100 0.162(5) 0.100(3) 0.107(4) 0.004(3) 0.022(4) 0.030(3) O200 0.106(3) 0.108(3) 0.062(3) 0.019(2) -0.003(2) -0.009(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 N11 C12 1.339(5) . ? N11 C16 1.352(6) . ? C12 C13 1.379(6) . ? C12 C22 1.499(6) . ? C13 C14 1.387(6) . ? C14 C15 1.371(7) . ? C15 C16 1.359(7) . ? N23 C24 1.333(5) . ? N23 C22 1.349(5) . ? C22 N21 1.331(5) . ? N21 C26 1.341(5) . ? C26 N25 1.346(5) . ? C26 C32 1.487(6) . ? N25 C24 1.337(5) . ? C24 N41 1.394(5) . ? N31 C36 1.332(7) . ? N31 C32 1.350(6) . ? C32 C33 1.385(6) . ? C33 C34 1.378(7) . ? C34 C35 1.364(7) . ? C35 C36 1.381(7) . ? N41 C42 1.378(6) . ? C42 O43 1.210(6) . ? C42 C44 1.544(7) . ? C44 C45 1.536(6) . ? C45 C47 1.515(7) . ? C45 C46 1.516(7) . ? C47 C48 1.519(8) . ? C48 C51 1.425(10) . ? C48 C50 1.481(9) . ? C48 C49 1.622(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N11 C16 116.5(4) . . ? N11 C12 C13 122.5(4) . . ? N11 C12 C22 117.0(4) . . ? C13 C12 C22 120.5(4) . . ? C12 C13 C14 119.1(5) . . ? C15 C14 C13 119.2(5) . . ? C16 C15 C14 117.9(5) . . ? N11 C16 C15 124.8(5) . . ? C24 N23 C22 114.3(4) . . ? N21 C22 N23 125.1(4) . . ? N21 C22 C12 119.0(4) . . ? N23 C22 C12 115.8(4) . . ? C22 N21 C26 115.3(4) . . ? N21 C26 N25 124.7(4) . . ? N21 C26 C32 116.4(4) . . ? N25 C26 C32 118.8(4) . . ? C24 N25 C26 114.5(4) . . ? N23 C24 N25 126.0(4) . . ? N23 C24 N41 114.4(4) . . ? N25 C24 N41 119.6(4) . . ? C36 N31 C32 116.8(4) . . ? N31 C32 C33 121.1(5) . . ? N31 C32 C26 117.8(4) . . ? C33 C32 C26 121.1(4) . . ? C34 C33 C32 120.6(4) . . ? C35 C34 C33 118.5(5) . . ? C34 C35 C36 117.8(5) . . ? N31 C36 C35 125.0(5) . . ? C42 N41 C24 126.7(4) . . ? O43 C42 N41 123.6(4) . . ? O43 C42 C44 122.4(4) . . ? N41 C42 C44 113.9(4) . . ? C45 C44 C42 111.7(4) . . ? C47 C45 C46 117.7(4) . . ? C47 C45 C44 109.3(4) . . ? C46 C45 C44 109.2(5) . . ? C45 C47 C48 122.1(4) . . ? C51 C48 C50 119.7(8) . . ? C51 C48 C47 116.4(6) . . ? C50 C48 C47 110.0(5) . . ? C51 C48 C49 102.6(8) . . ? C50 C48 C49 100.0(6) . . ? C47 C48 C49 105.2(7) . . ? _refine_diff_density_max 0.697 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.065 data_Yb(L7) complex _database_code_CSD 172881 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H29 N9 O14.5 Yb' _chemical_formula_weight 800.56 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.35(3) _cell_length_b 16.760(18) _cell_length_c 14.812(17) _cell_angle_alpha 90.00 _cell_angle_beta 103.488(10) _cell_angle_gamma 90.00 _cell_volume 5878(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used all _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.809 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3184 _exptl_absorpt_coefficient_mu 3.266 _exptl_absorpt_correction_type DIFABS(Walker and Stuart, 1983) _exptl_absorpt_correction_T_min 0.282 _exptl_absorpt_correction_T_max 1.000 _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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6980 _diffrn_reflns_av_R_equivalents 0.0762 _diffrn_reflns_av_sigmaI/netI 0.1184 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 26.12 _reflns_number_total 4420 _reflns_number_gt 1799 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.1840P)^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 4420 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2547 _refine_ls_R_factor_gt 0.1119 _refine_ls_wR_factor_ref 0.3363 _refine_ls_wR_factor_gt 0.2809 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Yb1 Yb 0.15760(5) 0.07512(7) 0.63833(7) 0.0536(5) Uani 1 d . . . N11 N 0.2167(10) -0.0508(14) 0.6329(14) 0.062(6) Uiso 1 d . . . C16 C 0.2702(12) -0.0434(17) 0.6338(17) 0.055(7) Uiso 1 d . . . C15 C 0.3070(13) -0.1114(19) 0.6379(18) 0.067(8) Uiso 1 d . . . H15 H 0.3447 -0.1049 0.6365 0.080 Uiso 1 calc R . . C14 C 0.2854(12) -0.1846(19) 0.6436(17) 0.063(7) Uiso 1 d . . . H14 H 0.3080 -0.2293 0.6436 0.076 Uiso 1 calc R . . C13 C 0.2350(15) -0.193(2) 0.649(2) 0.082(9) Uiso 1 d . . . H13 H 0.2209 -0.2438 0.6565 0.099 Uiso 1 calc R . . C12 C 0.1983(16) -0.122(2) 0.644(2) 0.091(10) Uiso 1 d . . . H12 H 0.1611 -0.1290 0.6486 0.109 Uiso 1 calc R . . N21 N 0.2525(9) 0.0964(13) 0.6264(13) 0.054(5) Uiso 1 d . . . C22 C 0.2928(12) 0.0385(18) 0.6294(17) 0.056(7) Uiso 1 d . . . N23 N 0.3486(10) 0.0459(15) 0.6298(14) 0.061(6) Uiso 1 d . . . C24 C 0.3623(12) 0.1206(18) 0.6266(16) 0.055(7) Uiso 1 d . . . N25 N 0.3303(9) 0.1847(13) 0.6216(13) 0.053(5) Uiso 1 d . . . C26 C 0.2764(11) 0.1723(16) 0.6240(15) 0.049(6) Uiso 1 d . . . N31 N 0.1847(8) 0.2171(12) 0.6139(12) 0.045(5) Uiso 1 d . . . C36 C 0.1446(10) 0.2753(16) 0.6064(14) 0.045(6) Uiso 1 d . . . H36 H 0.1071 0.2615 0.6023 0.054 Uiso 1 calc R . . C35 C 0.1595(13) 0.3532(19) 0.6050(18) 0.068(8) Uiso 1 d . . . H35 H 0.1323 0.3930 0.5999 0.081 Uiso 1 calc R . . C34 C 0.2175(13) 0.374(2) 0.6113(19) 0.071(8) Uiso 1 d . . . H34 H 0.2289 0.4268 0.6119 0.086 Uiso 1 calc R . . C33 C 0.2545(11) 0.3143(16) 0.6162(15) 0.051(6) Uiso 1 d . . . H33 H 0.2922 0.3250 0.6179 0.061 Uiso 1 calc R . . C32 C 0.2356(10) 0.2355(16) 0.6187(15) 0.047(6) Uiso 1 d . . . N41 N 0.4175(9) 0.1379(14) 0.6252(13) 0.055(5) Uiso 1 d . . . H41 H 0.4265 0.1876 0.6290 0.066 Uiso 1 calc R . . C42 C 0.4604(14) 0.086(2) 0.619(2) 0.078(9) Uiso 1 d . . . O43 O 0.4500(11) 0.0129(18) 0.6098(16) 0.108(8) Uiso 1 d . . . C51 C 0.5170(14) 0.123(2) 0.618(2) 0.077(9) Uiso 1 d . . . H51 H 0.5238 0.1662 0.6635 0.093 Uiso 1 calc R . . C52 C 0.5670(10) 0.0641(16) 0.6432(17) 0.053(6) Uiso 1 d . . . H52A H 0.5701 0.0457 0.7063 0.064 Uiso 1 calc R . . H52B H 0.5585 0.0180 0.6027 0.064 Uiso 1 calc R . . C53 C 0.6214(14) 0.096(2) 0.636(2) 0.076(9) Uiso 1 d . . . H53A H 0.6493 0.0541 0.6465 0.091 Uiso 1 calc R . . H53B H 0.6335 0.1365 0.6841 0.091 Uiso 1 calc R . . C54 C 0.6179(15) 0.134(2) 0.541(2) 0.089(10) Uiso 1 d . . . H54A H 0.6543 0.1574 0.5409 0.107 Uiso 1 calc R . . H54B H 0.6109 0.0920 0.4949 0.107 Uiso 1 calc R . . C55 C 0.5732(18) 0.197(3) 0.514(3) 0.122(14) Uiso 1 d . . . H55A H 0.5695 0.2122 0.4494 0.146 Uiso 1 calc R . . H55B H 0.5828 0.2438 0.5524 0.146 Uiso 1 calc R . . C56 C 0.5127(12) 0.1567(18) 0.5280(18) 0.063(7) Uiso 1 d . . . H56A H 0.4838 0.1977 0.5177 0.076 Uiso 1 calc R . . H56B H 0.5007 0.1156 0.4815 0.076 Uiso 1 calc R . . O100 O 0.0990(7) 0.1375(11) 0.7275(11) 0.055(4) Uiso 1 d . . . O101 O 0.1588(7) 0.0449(10) 0.4865(10) 0.050(4) Uiso 1 d . . . O102 O 0.0922(7) -0.0235(11) 0.6366(10) 0.053(4) Uiso 1 d . . . O103 O 0.0752(8) 0.1259(11) 0.5341(11) 0.060(5) Uiso 1 d . . . O51 O 0.0804(10) 0.0799(15) 0.3133(15) 0.092(7) Uiso 1 d . . . O52 O 0.0705(10) 0.1942(15) 0.2321(15) 0.095(7) Uiso 1 d . . . N53 N 0.0716(10) 0.1573(15) 0.3030(15) 0.061(6) Uiso 1 d . . . O54 O 0.0677(9) 0.1954(13) 0.3745(13) 0.077(6) Uiso 1 d . . . N43 N 0.2138(8) 0.0753(13) 0.8362(12) 0.045(5) Uiso 1 d . . . O44 O 0.2323(7) 0.0707(12) 0.9187(11) 0.062(5) Uiso 1 d . . . O41 O 0.2207(8) 0.1316(12) 0.7863(12) 0.065(5) Uiso 1 d . . . O42 O 0.1843(8) 0.0177(13) 0.7936(12) 0.071(5) Uiso 1 d . . . N63 N -0.0515(10) 0.1180(15) 0.5884(14) 0.059(6) Uiso 1 d . . . O61 O -0.1041(11) 0.1156(16) 0.5840(16) 0.098(7) Uiso 1 d . . . O62 O -0.0180(9) 0.1504(14) 0.6523(14) 0.081(6) Uiso 1 d . . . O64 O -0.0328(8) 0.0865(12) 0.5217(13) 0.071(5) Uiso 1 d . . . O1 O 0.5317(18) 0.156(3) 0.244(3) 0.079(12) Uiso 0.50 d P . . 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 0.0590(8) 0.0553(8) 0.0460(7) 0.0018(6) 0.0114(4) -0.0031(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Yb1 O102 2.290(18) . ? Yb1 O101 2.313(15) . ? Yb1 O103 2.385(18) . ? Yb1 N21 2.39(2) . ? Yb1 O100 2.398(16) . ? Yb1 O42 2.437(19) . ? Yb1 N31 2.52(2) . ? Yb1 O41 2.548(18) . ? Yb1 N11 2.57(2) . ? N11 C12 1.30(4) . ? N11 C16 1.30(3) . ? C16 C15 1.44(4) . ? C16 C22 1.49(4) . ? C15 C14 1.34(4) . ? C14 C13 1.26(4) . ? C13 C12 1.48(5) . ? N21 C22 1.37(3) . ? N21 C26 1.40(3) . ? C22 N23 1.36(3) . ? N23 C24 1.30(3) . ? C24 N25 1.32(3) . ? C24 N41 1.38(3) . ? N25 C26 1.34(3) . ? C26 C32 1.44(4) . ? N31 C32 1.26(3) . ? N31 C36 1.37(3) . ? C36 C35 1.36(4) . ? C35 C34 1.44(4) . ? C34 C33 1.33(4) . ? C33 C32 1.40(4) . ? N41 C42 1.38(4) . ? C42 O43 1.25(4) . ? C42 C51 1.51(4) . ? C51 C56 1.43(4) . ? C51 C52 1.54(4) . ? C52 C53 1.46(4) . ? C53 C54 1.52(4) . ? C54 C55 1.50(5) . ? C55 C56 1.68(5) . ? O51 N53 1.32(3) . ? O52 N53 1.21(3) . ? N53 O54 1.26(3) . ? N43 O44 1.20(2) . ? N43 O41 1.23(2) . ? N43 O42 1.28(3) . ? N63 O62 1.22(3) . ? N63 O61 1.27(3) . ? N63 O64 1.29(3) . ? 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 O102 Yb1 O101 89.8(6) . . ? O102 Yb1 O103 76.8(6) . . ? O101 Yb1 O103 69.4(6) . . ? O102 Yb1 N21 142.2(7) . . ? O101 Yb1 N21 74.2(6) . . ? O103 Yb1 N21 125.6(6) . . ? O102 Yb1 O100 79.6(6) . . ? O101 Yb1 O100 140.9(6) . . ? O103 Yb1 O100 71.5(6) . . ? N21 Yb1 O100 133.3(7) . . ? O102 Yb1 O42 76.0(6) . . ? O101 Yb1 O42 140.4(6) . . ? O103 Yb1 O42 138.6(6) . . ? N21 Yb1 O42 94.6(7) . . ? O100 Yb1 O42 73.4(6) . . ? O102 Yb1 N31 152.2(6) . . ? O101 Yb1 N31 90.2(6) . . ? O103 Yb1 N31 77.2(6) . . ? N21 Yb1 N31 63.7(7) . . ? O100 Yb1 N31 82.9(6) . . ? O42 Yb1 N31 119.2(6) . . ? O102 Yb1 O41 123.8(6) . . ? O101 Yb1 O41 140.9(6) . . ? O103 Yb1 O41 132.2(6) . . ? N21 Yb1 O41 66.9(6) . . ? O100 Yb1 O41 71.4(6) . . ? O42 Yb1 O41 50.2(7) . . ? N31 Yb1 O41 69.3(6) . . ? O102 Yb1 N11 78.4(7) . . ? O101 Yb1 N11 69.8(6) . . ? O103 Yb1 N11 131.8(7) . . ? N21 Yb1 N11 64.0(7) . . ? O100 Yb1 N11 141.7(6) . . ? O42 Yb1 N11 71.1(7) . . ? N31 Yb1 N11 127.2(7) . . ? O41 Yb1 N11 95.9(7) . . ? C12 N11 C16 117(3) . . ? C12 N11 Yb1 123(2) . . ? C16 N11 Yb1 119.1(19) . . ? N11 C16 C15 122(3) . . ? N11 C16 C22 118(3) . . ? C15 C16 C22 120(2) . . ? C14 C15 C16 118(3) . . ? C13 C14 C15 121(3) . . ? C14 C13 C12 120(4) . . ? N11 C12 C13 122(3) . . ? C22 N21 C26 110(2) . . ? C22 N21 Yb1 126.0(18) . . ? C26 N21 Yb1 123.5(16) . . ? N23 C22 N21 130(3) . . ? N23 C22 C16 118(3) . . ? N21 C22 C16 113(2) . . ? C24 N23 C22 111(2) . . ? N23 C24 N25 129(3) . . ? N23 C24 N41 117(3) . . ? N25 C24 N41 113(3) . . ? C24 N25 C26 116(2) . . ? N25 C26 N21 124(2) . . ? N25 C26 C32 124(2) . . ? N21 C26 C32 113(2) . . ? C32 N31 C36 120(2) . . ? C32 N31 Yb1 120.6(17) . . ? C36 N31 Yb1 118.6(15) . . ? C35 C36 N31 120(2) . . ? C36 C35 C34 120(3) . . ? C33 C34 C35 118(3) . . ? C34 C33 C32 119(3) . . ? N31 C32 C33 124(2) . . ? N31 C32 C26 119(2) . . ? C33 C32 C26 118(2) . . ? C24 N41 C42 128(3) . . ? O43 C42 N41 119(3) . . ? O43 C42 C51 124(3) . . ? N41 C42 C51 116(3) . . ? C56 C51 C42 107(3) . . ? C56 C51 C52 111(3) . . ? C42 C51 C52 114(3) . . ? C53 C52 C51 115(3) . . ? C52 C53 C54 111(3) . . ? C55 C54 C53 115(3) . . ? C54 C55 C56 107(3) . . ? C51 C56 C55 114(3) . . ? O52 N53 O54 119(3) . . ? O52 N53 O51 125(2) . . ? O54 N53 O51 116(2) . . ? O44 N43 O41 126(2) . . ? O44 N43 O42 119(2) . . ? O41 N43 O42 114.9(19) . . ? N43 O41 Yb1 95.3(14) . . ? N43 O42 Yb1 99.4(14) . . ? O62 N63 O61 122(2) . . ? O62 N63 O64 119(2) . . ? O61 N63 O64 119(2) . . ? _refine_diff_density_max 3.540 _refine_diff_density_min -1.922 _refine_diff_density_rms 0.255 _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands Walker, N. and Stuart, D., (1983) Acta Cryst A39 158. ; data_5 _database_code_CSD 172882 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H28 N11 O10 Yb' _chemical_formula_weight 803.61 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.935(14) _cell_length_b 12.887(14) _cell_length_c 15.004(17) _cell_angle_alpha 71.688(10) _cell_angle_beta 87.138(10) _cell_angle_gamma 78.955(10) _cell_volume 1610(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used all _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 798 _exptl_absorpt_coefficient_mu 2.974 _exptl_absorpt_correction_type DIFABS(Walker and Stuart, 1983) _exptl_absorpt_correction_T_min 0.623 _exptl_absorpt_correction_T_max 1.000 _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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5198 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 25.90 _reflns_number_total 5198 _reflns_number_gt 4699 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+4.8052P] 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 5198 _refine_ls_number_parameters 428 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0755 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Yb Yb 0.27341(2) 0.205671(15) 0.131680(13) 0.03225(8) Uani 1 d . . . N11 N 0.4852(4) 0.3123(3) 0.0917(3) 0.0352(8) Uani 1 d . . . C12 C 0.5681(6) 0.3280(4) 0.1566(3) 0.0452(12) Uani 1 d . . . H12 H 0.5369 0.3068 0.2187 0.054 Uiso 1 calc R . . C13 C 0.6977(6) 0.3743(4) 0.1356(4) 0.0502(13) Uani 1 d . . . H13 H 0.7529 0.3829 0.1829 0.060 Uiso 1 calc R . . C14 C 0.7444(6) 0.4074(4) 0.0437(4) 0.0463(12) Uani 1 d . . . H14 H 0.8314 0.4388 0.0280 0.056 Uiso 1 calc R . . C15 C 0.6597(6) 0.3934(4) -0.0246(3) 0.0388(10) Uani 1 d . . . H15 H 0.6879 0.4158 -0.0873 0.047 Uiso 1 calc R . . C16 C 0.5324(5) 0.3454(3) 0.0017(3) 0.0314(9) Uani 1 d . . . N21 N 0.3139(4) 0.2816(3) -0.0350(2) 0.0309(8) Uani 1 d . . . C22 C 0.4367(5) 0.3270(3) -0.0678(3) 0.0310(9) Uani 1 d . . . N23 N 0.4777(5) 0.3557(3) -0.1570(3) 0.0377(9) Uani 1 d . . . C24 C 0.3823(6) 0.3377(4) -0.2153(3) 0.0385(10) Uani 1 d . . . N25 N 0.2524(5) 0.3023(3) -0.1923(3) 0.0394(9) Uani 1 d . . . C26 C 0.2254(5) 0.2725(4) -0.1006(3) 0.0331(9) Uani 1 d . . . N31 N 0.0768(4) 0.1831(3) 0.0279(3) 0.0384(9) Uani 1 d . . . C32 C 0.0888(5) 0.2225(4) -0.0662(3) 0.0364(10) Uani 1 d . . . C33 C -0.0171(6) 0.2159(5) -0.1279(4) 0.0499(13) Uani 1 d . . . H33 H -0.0059 0.2447 -0.1925 0.060 Uiso 1 calc R . . C34 C -0.1389(7) 0.1658(5) -0.0914(5) 0.0581(15) Uani 1 d . . . H34 H -0.2125 0.1612 -0.1310 0.070 Uiso 1 calc R . . C35 C -0.1509(7) 0.1223(5) 0.0045(5) 0.0571(15) Uani 1 d . . . H35 H -0.2306 0.0859 0.0304 0.069 Uiso 1 calc R . . C36 C -0.0431(6) 0.1337(4) 0.0612(4) 0.0485(12) Uani 1 d . . . H36 H -0.0535 0.1057 0.1259 0.058 Uiso 1 calc R . . O41 O 0.0868(5) 0.1551(4) 0.2364(3) 0.0599(10) Uani 1 d . . . N43 N 0.0587(7) 0.1666(5) 0.3178(4) 0.0696(15) Uani 1 d . . . O42 O 0.1554(7) 0.1209(5) 0.3806(3) 0.0959(17) Uani 1 d . . . O44 C -0.0540(8) 0.2292(8) 0.3269(6) 0.090(3) Uani 1 d . . . O51 O 0.1028(4) 0.3780(3) 0.0839(2) 0.0461(8) Uani 1 d . . . N53 N 0.1197(5) 0.4099(3) 0.1538(3) 0.0421(9) Uani 1 d . . . O52 O 0.2201(4) 0.3475(3) 0.2137(2) 0.0495(9) Uani 1 d . . . O54 O 0.0439(5) 0.4958(3) 0.1614(3) 0.0670(12) Uani 1 d . . . O61 O 0.4934(5) 0.0877(3) 0.0947(3) 0.0546(10) Uani 1 d . . . N63 N 0.4390(6) 0.0001(4) 0.1209(3) 0.0528(12) Uani 1 d . . . O62 O 0.3036(5) 0.0102(3) 0.1517(3) 0.0605(10) Uani 1 d . . . O64 O 0.5098(6) -0.0894(4) 0.1195(4) 0.0882(16) Uani 1 d . . . O100 O 0.4105(5) 0.1315(3) 0.2700(3) 0.0516(9) Uani 1 d D . . H1 H 0.346(8) 0.107(7) 0.305(6) 0.12(4) Uiso 1 d D . . H2 H 0.500(3) 0.112(5) 0.278(4) 0.07(2) Uiso 1 d D . . N41 N 0.4357(5) 0.3593(4) -0.3059(3) 0.0467(10) Uani 1 d . . . H41 H 0.5213 0.3821 -0.3155 0.056 Uiso 1 calc R . . C42 C 0.3677(7) 0.3488(5) -0.3850(3) 0.0505(13) Uani 1 d . . . O43 O 0.2375(6) 0.3350(5) -0.3857(3) 0.0795(15) Uani 1 d . . . C44 C 0.4744(7) 0.3583(5) -0.4665(3) 0.0514(13) Uani 1 d . . . H44A H 0.5565 0.3930 -0.4563 0.062 Uiso 1 calc R . . H44B H 0.4195 0.4073 -0.5228 0.062 Uiso 1 calc R . . C45 C 0.5446(8) 0.2478(6) -0.4836(5) 0.0688(17) Uani 1 d . . . C46 C 0.4246(11) 0.1998(8) -0.5162(7) 0.105(3) Uani 1 d . . . H46A H 0.3793 0.2513 -0.5738 0.125 Uiso 1 calc R . . H46B H 0.3475 0.1868 -0.4692 0.125 Uiso 1 calc R . . H46C H 0.4707 0.1309 -0.5264 0.125 Uiso 1 calc R . . C47 C 0.6180(11) 0.1662(7) -0.3928(7) 0.110(3) Uani 1 d . . . H47A H 0.5412 0.1515 -0.3458 0.132 Uiso 1 calc R . . H47B H 0.6932 0.1976 -0.3717 0.132 Uiso 1 calc R . . H47C H 0.6659 0.0980 -0.4037 0.132 Uiso 1 calc R . . C48 C 0.6616(14) 0.2724(11) -0.5595(8) 0.154(5) Uani 1 d . . . H48A H 0.6931 0.2088 -0.5809 0.185 Uiso 1 calc R . . H48B H 0.7482 0.2888 -0.5350 0.185 Uiso 1 calc R . . H48C H 0.6178 0.3352 -0.6111 0.185 Uiso 1 calc R . . N400 N 0.2367(10) 0.5827(7) 0.3414(5) 0.106(3) Uani 1 d . . . C401 C 0.1504(9) 0.5262(7) 0.3609(5) 0.0736(19) Uani 1 d . . . C402 C 0.0431(9) 0.4525(7) 0.3881(5) 0.080(2) Uani 1 d . . . H40A H 0.0372 0.4264 0.4553 0.095 Uiso 1 calc R . . H40B H 0.0757 0.3903 0.3651 0.095 Uiso 1 calc R . . H40C H -0.0555 0.4914 0.3621 0.095 Uiso 1 calc R . . N500 N -0.2922(10) 0.0178(8) 0.3013(7) 0.141(4) Uani 1 d . . . C501 C -0.1821(10) -0.0378(8) 0.3303(7) 0.102(3) Uani 1 d . . . C502 C -0.0434(11) -0.1114(8) 0.3682(8) 0.127(4) Uani 1 d . . . H50A H 0.0327 -0.1052 0.3202 0.153 Uiso 1 calc R . . H50B H -0.0607 -0.1865 0.3903 0.153 Uiso 1 calc R . . H50C H -0.0088 -0.0920 0.4193 0.153 Uiso 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 Yb 0.03074(13) 0.03262(12) 0.03405(11) -0.01124(8) 0.00069(7) -0.00604(7) N11 0.037(2) 0.035(2) 0.036(2) -0.0120(16) -0.0038(15) -0.0075(15) C12 0.052(3) 0.052(3) 0.035(2) -0.013(2) -0.006(2) -0.016(2) C13 0.052(4) 0.051(3) 0.051(3) -0.014(2) -0.018(2) -0.014(2) C14 0.036(3) 0.041(3) 0.060(3) -0.010(2) -0.007(2) -0.012(2) C15 0.036(3) 0.035(3) 0.044(3) -0.010(2) -0.0005(19) -0.0064(19) C16 0.033(3) 0.028(2) 0.034(2) -0.0120(17) -0.0038(17) -0.0031(17) N21 0.032(2) 0.031(2) 0.0301(18) -0.0096(15) -0.0037(14) -0.0057(14) C22 0.035(3) 0.029(2) 0.030(2) -0.0098(17) -0.0028(17) -0.0047(17) N23 0.038(2) 0.040(2) 0.037(2) -0.0141(17) -0.0012(16) -0.0100(16) C24 0.045(3) 0.035(3) 0.034(2) -0.0126(19) -0.0002(19) -0.001(2) N25 0.038(2) 0.044(2) 0.037(2) -0.0156(17) -0.0066(16) -0.0033(17) C26 0.033(3) 0.029(2) 0.037(2) -0.0121(17) -0.0047(17) -0.0001(17) N31 0.032(2) 0.039(2) 0.047(2) -0.0155(17) -0.0014(16) -0.0079(16) C32 0.032(3) 0.035(3) 0.045(3) -0.018(2) -0.0052(18) -0.0043(18) C33 0.043(3) 0.055(3) 0.058(3) -0.023(3) -0.010(2) -0.010(2) C34 0.042(4) 0.059(4) 0.084(4) -0.034(3) -0.016(3) -0.011(3) C35 0.043(4) 0.048(3) 0.090(5) -0.031(3) 0.004(3) -0.014(2) C36 0.044(3) 0.044(3) 0.062(3) -0.020(2) 0.004(2) -0.015(2) O41 0.054(3) 0.079(3) 0.057(2) -0.028(2) 0.0174(18) -0.030(2) N43 0.066(4) 0.096(4) 0.059(3) -0.030(3) 0.022(3) -0.039(3) O42 0.107(5) 0.123(5) 0.050(3) -0.016(3) 0.008(3) -0.023(3) O44 0.041(4) 0.150(8) 0.093(5) -0.077(5) 0.022(3) 0.005(4) O51 0.049(2) 0.045(2) 0.0453(19) -0.0205(16) -0.0052(15) 0.0010(15) N53 0.043(3) 0.040(2) 0.045(2) -0.0181(18) 0.0056(18) -0.0054(18) O52 0.049(2) 0.053(2) 0.049(2) -0.0211(17) -0.0055(16) -0.0034(16) O54 0.084(3) 0.046(2) 0.068(3) -0.029(2) 0.008(2) 0.010(2) O61 0.054(3) 0.045(2) 0.057(2) -0.0137(17) 0.0128(18) 0.0004(17) N63 0.068(4) 0.039(3) 0.049(3) -0.017(2) -0.010(2) 0.005(2) O62 0.061(3) 0.038(2) 0.084(3) -0.0204(19) -0.009(2) -0.0088(17) O64 0.103(4) 0.046(3) 0.107(4) -0.035(3) -0.015(3) 0.029(3) O100 0.048(3) 0.058(2) 0.042(2) -0.0082(17) -0.0077(18) -0.0030(19) N41 0.049(3) 0.060(3) 0.034(2) -0.0163(19) -0.0022(17) -0.012(2) C42 0.058(4) 0.057(3) 0.037(3) -0.019(2) -0.007(2) -0.005(3) O43 0.067(3) 0.151(5) 0.041(2) -0.048(3) 0.0017(19) -0.038(3) C44 0.064(4) 0.055(3) 0.031(2) -0.007(2) -0.002(2) -0.011(3) C45 0.070(5) 0.077(5) 0.069(4) -0.040(3) 0.016(3) -0.011(3) C46 0.115(8) 0.122(7) 0.111(7) -0.079(6) 0.010(5) -0.035(6) C47 0.087(7) 0.081(6) 0.151(9) -0.040(6) -0.017(6) 0.024(5) C48 0.141(10) 0.211(13) 0.156(10) -0.116(10) 0.098(9) -0.063(9) N400 0.108(7) 0.129(7) 0.082(5) -0.010(4) -0.022(4) -0.054(5) C401 0.076(6) 0.086(5) 0.058(4) -0.020(3) -0.014(3) -0.011(4) C402 0.075(5) 0.099(6) 0.074(5) -0.036(4) 0.009(4) -0.025(4) N500 0.078(6) 0.151(8) 0.138(7) 0.020(6) -0.024(5) 0.009(5) C501 0.057(6) 0.102(7) 0.118(7) 0.004(5) -0.009(4) -0.007(4) C502 0.065(7) 0.116(8) 0.171(10) -0.011(7) -0.023(6) 0.003(5) _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 Yb O41 2.277(4) . ? Yb O100 2.298(4) . ? Yb O51 2.362(4) . ? Yb O61 2.400(4) . ? Yb O62 2.404(4) . ? Yb N21 2.419(4) . ? Yb O52 2.470(4) . ? Yb N11 2.489(5) . ? Yb N31 2.519(5) . ? N11 C12 1.338(6) . ? N11 C16 1.353(6) . ? C12 C13 1.380(8) . ? C13 C14 1.378(8) . ? C14 C15 1.378(7) . ? C15 C16 1.379(7) . ? C16 C22 1.482(6) . ? N21 C26 1.339(6) . ? N21 C22 1.342(6) . ? C22 N23 1.324(6) . ? N23 C24 1.350(6) . ? C24 N25 1.319(7) . ? C24 N41 1.379(6) . ? N25 C26 1.330(6) . ? C26 C32 1.483(7) . ? N31 C36 1.346(7) . ? N31 C32 1.348(6) . ? C32 C33 1.389(7) . ? C33 C34 1.374(8) . ? C34 C35 1.377(9) . ? C35 C36 1.374(8) . ? O41 N43 1.282(6) . ? N43 O44 1.196(9) . ? N43 O42 1.232(8) . ? O51 N53 1.266(5) . ? N53 O54 1.216(5) . ? N53 O52 1.269(5) . ? O61 N63 1.255(6) . ? N63 O64 1.211(6) . ? N63 O62 1.271(7) . ? N41 C42 1.415(6) . ? C42 O43 1.212(7) . ? C42 C44 1.501(8) . ? C44 C45 1.536(8) . ? C45 C46 1.505(10) . ? C45 C48 1.508(11) . ? C45 C47 1.522(11) . ? N400 C401 1.126(10) . ? C401 C402 1.434(11) . ? N500 C501 1.116(10) . ? C501 C502 1.429(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O41 Yb O100 78.75(19) . . ? O41 Yb O51 83.26(16) . . ? O100 Yb O51 126.35(13) . . ? O41 Yb O61 127.87(16) . . ? O100 Yb O61 75.94(16) . . ? O51 Yb O61 147.24(13) . . ? O41 Yb O62 78.15(16) . . ? O100 Yb O62 79.20(15) . . ? O51 Yb O62 144.53(15) . . ? O61 Yb O62 52.85(15) . . ? O41 Yb N21 141.27(15) . . ? O100 Yb N21 139.81(16) . . ? O51 Yb N21 74.83(12) . . ? O61 Yb N21 73.57(13) . . ? O62 Yb N21 101.87(14) . . ? O41 Yb O52 74.29(15) . . ? O100 Yb O52 73.76(15) . . ? O51 Yb O52 52.71(13) . . ? O61 Yb O52 137.09(14) . . ? O62 Yb O52 144.43(15) . . ? N21 Yb O52 113.70(14) . . ? O41 Yb N11 145.47(14) . . ? O100 Yb N11 80.23(16) . . ? O51 Yb N11 87.55(16) . . ? O61 Yb N11 71.80(16) . . ? O62 Yb N11 124.02(15) . . ? N21 Yb N11 65.80(12) . . ? O52 Yb N11 73.69(14) . . ? O41 Yb N31 78.43(17) . . ? O100 Yb N31 146.92(15) . . ? O51 Yb N31 73.93(14) . . ? O61 Yb N31 100.06(16) . . ? O62 Yb N31 72.91(14) . . ? N21 Yb N31 65.09(14) . . ? O52 Yb N31 121.76(13) . . ? N11 Yb N31 130.46(14) . . ? C12 N11 C16 117.1(4) . . ? C12 N11 Yb 123.0(3) . . ? C16 N11 Yb 119.5(3) . . ? N11 C12 C13 123.0(5) . . ? C14 C13 C12 119.2(5) . . ? C13 C14 C15 118.8(5) . . ? C14 C15 C16 118.8(5) . . ? N11 C16 C15 123.1(4) . . ? N11 C16 C22 115.2(4) . . ? C15 C16 C22 121.7(4) . . ? C26 N21 C22 115.1(4) . . ? C26 N21 Yb 123.3(3) . . ? C22 N21 Yb 121.3(3) . . ? N23 C22 N21 124.6(4) . . ? N23 C22 C16 118.5(4) . . ? N21 C22 C16 117.0(4) . . ? C22 N23 C24 114.2(4) . . ? N25 C24 N23 126.4(4) . . ? N25 C24 N41 121.2(4) . . ? N23 C24 N41 112.4(4) . . ? C24 N25 C26 114.0(4) . . ? N25 C26 N21 125.3(4) . . ? N25 C26 C32 118.5(4) . . ? N21 C26 C32 116.2(4) . . ? C36 N31 C32 116.8(4) . . ? C36 N31 Yb 123.5(3) . . ? C32 N31 Yb 119.7(3) . . ? N31 C32 C33 123.1(5) . . ? N31 C32 C26 115.5(4) . . ? C33 C32 C26 121.4(4) . . ? C34 C33 C32 118.4(5) . . ? C33 C34 C35 119.4(5) . . ? C36 C35 C34 118.9(5) . . ? N31 C36 C35 123.4(5) . . ? N43 O41 Yb 131.3(3) . . ? O44 N43 O42 122.8(7) . . ? O44 N43 O41 118.2(7) . . ? O42 N43 O41 118.7(6) . . ? N53 O51 Yb 98.3(3) . . ? O54 N53 O51 121.1(4) . . ? O54 N53 O52 123.1(4) . . ? O51 N53 O52 115.8(4) . . ? N53 O52 Yb 93.0(3) . . ? N63 O61 Yb 96.1(3) . . ? O64 N63 O61 123.3(6) . . ? O64 N63 O62 121.0(5) . . ? O61 N63 O62 115.6(4) . . ? N63 O62 Yb 95.5(3) . . ? C24 N41 C42 128.2(5) . . ? O43 C42 N41 122.9(5) . . ? O43 C42 C44 124.9(5) . . ? N41 C42 C44 112.2(5) . . ? C42 C44 C45 115.1(5) . . ? C46 C45 C48 109.0(7) . . ? C46 C45 C47 109.7(7) . . ? C48 C45 C47 111.1(8) . . ? C46 C45 C44 110.8(6) . . ? C48 C45 C44 107.2(7) . . ? C47 C45 C44 109.1(6) . . ? N400 C401 C402 178.4(8) . . ? N500 C501 C502 178.5(12) . . ? _refine_diff_density_max 0.997 _refine_diff_density_min -1.596 _refine_diff_density_rms 0.094