Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Michael Hill' _publ_contact_author_address ; Department of Chemistry Imperial College London South Kensington London SW7 2AZ UNITED KINGDOM ; _publ_contact_author_email MIKE.HILL@IMPERIAL.AC.UK _publ_section_title ; Racemic N-aryl Bis(amidines) and Bis(amidinates): A case of 'Steric Overkill' in the Search for Enantioselective Organolanthanide Catalysts ; _publ_requested_category FO loop_ _publ_author_name 'Michael Hill' 'P. B. Hitchcock' 'Stephen M. Mansell' # Attachment 'msh2-sep-2005.cif' data_(3)-jun1304 _database_code_depnum_ccdc_archive 'CCDC 284724' _audit_creation_date 2004-06-23T09:30:45-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C40 H64 N4' _chemical_formula_sum 'C40 H64 N4' _chemical_formula_weight 600.95 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7004(2) _cell_length_b 9.6692(1) _cell_length_c 24.4085(6) _cell_angle_alpha 89.477(1) _cell_angle_beta 88.641(1) _cell_angle_gamma 68.790(1) _cell_volume 1913.75(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 14787 _cell_measurement_theta_min 3.705 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.043 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.06 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.698284E-1 _diffrn_orient_matrix_ub_12 -0.70649E-2 _diffrn_orient_matrix_ub_13 0.326294E-1 _diffrn_orient_matrix_ub_21 0.101519 _diffrn_orient_matrix_ub_22 -0.487956E-1 _diffrn_orient_matrix_ub_23 -0.230862E-1 _diffrn_orient_matrix_ub_31 0.50224E-2 _diffrn_orient_matrix_ub_32 0.993769E-1 _diffrn_orient_matrix_ub_33 -0.90433E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_unetI/netI 0.0313 _diffrn_reflns_number 21923 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.72 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 6677 _reflns_number_gt 5557 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; H on N were refined; other H were riding. 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^)+(0.0516P)^2^+0.8463P] 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_number_reflns 6677 _refine_ls_number_parameters 405 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1282 _refine_ls_wR_factor_gt 0.12 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.306 _refine_diff_density_min -0.27 _refine_diff_density_rms 0.032 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 N1 N 0.62779(17) 0.26295(15) 0.22033(5) 0.0345(3) Uani 1 1 d . . . H1N H 0.719(3) 0.274(2) 0.2238(8) 0.050(6) Uiso 1 1 d . . . N2 N 0.60690(17) 0.11229(14) 0.31937(6) 0.0371(3) Uani 1 1 d . . . H2N H 0.556(2) 0.080(2) 0.2958(8) 0.049(5) Uiso 1 1 d . . . N3 N 0.44632(15) 0.23215(14) 0.16180(5) 0.0304(3) Uani 1 1 d . . . N4 N 0.83141(15) 0.02570(13) 0.37982(5) 0.0308(3) Uani 1 1 d . . . C1 C 0.50159(17) 0.33269(15) 0.26206(6) 0.0274(3) Uani 1 1 d . . . H1 H 0.4023 0.308 0.2541 0.033 Uiso 1 1 calc R . . C2 C 0.56064(17) 0.27324(15) 0.31894(6) 0.0264(3) Uani 1 1 d . . . H2 H 0.6608 0.2967 0.3268 0.032 Uiso 1 1 calc R . . C3 C 0.42833(19) 0.34909(18) 0.36205(6) 0.0349(4) Uani 1 1 d . . . H3B H 0.4696 0.3117 0.3988 0.042 Uiso 1 1 calc R . . H3A H 0.3296 0.324 0.3556 0.042 Uiso 1 1 calc R . . C4 C 0.3805(2) 0.51700(19) 0.36058(7) 0.0442(4) Uani 1 1 d . . . H4B H 0.291 0.563 0.3879 0.053 Uiso 1 1 calc R . . H4A H 0.4766 0.5428 0.3705 0.053 Uiso 1 1 calc R . . C5 C 0.3231(2) 0.57830(18) 0.30406(7) 0.0451(4) Uani 1 1 d . . . H5B H 0.2185 0.5643 0.2962 0.054 Uiso 1 1 calc R . . H5A H 0.3017 0.686 0.3033 0.054 Uiso 1 1 calc R . . C6 C 0.4514(2) 0.50121(17) 0.26028(7) 0.0379(4) Uani 1 1 d . . . H6B H 0.5503 0.5271 0.2653 0.045 Uiso 1 1 calc R . . H6A H 0.4068 0.5377 0.2238 0.045 Uiso 1 1 calc R . . C7 C 0.59031(18) 0.23448(15) 0.16820(6) 0.0279(3) Uani 1 1 d . . . C8 C 0.73483(19) 0.20893(18) 0.12665(6) 0.0351(4) Uani 1 1 d . . . C9 C 0.7743(3) 0.3514(3) 0.12303(9) 0.0663(6) Uani 1 1 d . . . H9C H 0.6778 0.4331 0.1098 0.099 Uiso 1 1 calc R . . H9B H 0.8678 0.3361 0.0976 0.099 Uiso 1 1 calc R . . H9A H 0.8025 0.376 0.1594 0.099 Uiso 1 1 calc R . . C10 C 0.8862(2) 0.0805(3) 0.14586(9) 0.0681(6) Uani 1 1 d . . . H10C H 0.9165 0.1031 0.1822 0.102 Uiso 1 1 calc R . . H10B H 0.9783 0.0663 0.1199 0.102 Uiso 1 1 calc R . . H10A H 0.861 -0.0104 0.1478 0.102 Uiso 1 1 calc R . . C11 C 0.6971(2) 0.1742(2) 0.06865(7) 0.0497(5) Uani 1 1 d . . . H11C H 0.6702 0.0841 0.0692 0.075 Uiso 1 1 calc R . . H11B H 0.7938 0.1588 0.0446 0.075 Uiso 1 1 calc R . . H11A H 0.6032 0.2574 0.0549 0.075 Uiso 1 1 calc R . . C12 C 0.37216(18) 0.20578(17) 0.11429(6) 0.0311(3) Uani 1 1 d . . . C13 C 0.3792(2) 0.06163(18) 0.10230(6) 0.0357(4) Uani 1 1 d . . . C14 C 0.2916(2) 0.0417(2) 0.05794(7) 0.0418(4) Uani 1 1 d . . . H14 H 0.2967 -0.0554 0.0492 0.05 Uiso 1 1 calc R . . C15 C 0.1979(2) 0.1598(2) 0.02657(7) 0.0448(4) Uani 1 1 d . . . H15 H 0.1394 0.144 -0.0037 0.054 Uiso 1 1 calc R . . C16 C 0.1892(2) 0.3014(2) 0.03931(7) 0.0421(4) Uani 1 1 d . . . H16 H 0.1242 0.3824 0.0175 0.051 Uiso 1 1 calc R . . C17 C 0.27374(19) 0.32816(18) 0.08335(6) 0.0347(4) Uani 1 1 d . . . C18 C 0.4747(2) -0.06869(19) 0.13814(8) 0.0458(4) Uani 1 1 d . . . H18 H 0.5521 -0.0382 0.1604 0.055 Uiso 1 1 calc R . . C19 C 0.3581(4) -0.1061(3) 0.17724(10) 0.1025(11) Uani 1 1 d . . . H19C H 0.2843 -0.1411 0.1564 0.154 Uiso 1 1 calc R . . H19B H 0.2927 -0.0173 0.1981 0.154 Uiso 1 1 calc R . . H19A H 0.4216 -0.184 0.2025 0.154 Uiso 1 1 calc R . . C20 C 0.5754(3) -0.2067(2) 0.10664(11) 0.0830(8) Uani 1 1 d . . . H20C H 0.5022 -0.2391 0.0845 0.124 Uiso 1 1 calc R . . H20B H 0.6338 -0.2855 0.1324 0.124 Uiso 1 1 calc R . . H20A H 0.6556 -0.1849 0.0826 0.124 Uiso 1 1 calc R . . C21 C 0.2560(2) 0.48478(19) 0.09935(7) 0.0430(4) Uani 1 1 d . . . H21 H 0.361 0.4776 0.1172 0.052 Uiso 1 1 calc R . . C22 C 0.2348(4) 0.5890(3) 0.05062(10) 0.0836(8) Uani 1 1 d . . . H22C H 0.1308 0.6021 0.0327 0.125 Uiso 1 1 calc R . . H22B H 0.3268 0.5466 0.0244 0.125 Uiso 1 1 calc R . . H22A H 0.2332 0.6854 0.0633 0.125 Uiso 1 1 calc R . . C23 C 0.1186(3) 0.5458(3) 0.14209(12) 0.0811(8) Uani 1 1 d . . . H23C H 0.0142 0.5491 0.1269 0.122 Uiso 1 1 calc R . . H23B H 0.1097 0.6462 0.1525 0.122 Uiso 1 1 calc R . . H23A H 0.1435 0.4816 0.1745 0.122 Uiso 1 1 calc R . . C24 C 0.73569(17) 0.00757(15) 0.34433(6) 0.0259(3) Uani 1 1 d . . . C25 C 0.76913(19) -0.15214(16) 0.32523(6) 0.0335(4) Uani 1 1 d . . . C26 C 0.8863(3) -0.26165(18) 0.36423(8) 0.0552(5) Uani 1 1 d . . . H26C H 0.836 -0.2488 0.4011 0.083 Uiso 1 1 calc R . . H26B H 0.99 -0.2436 0.3651 0.083 Uiso 1 1 calc R . . H26A H 0.9083 -0.3631 0.3516 0.083 Uiso 1 1 calc R . . C27 C 0.8507(3) -0.1711(2) 0.26813(8) 0.0515(5) Uani 1 1 d . . . H27C H 0.9522 -0.1494 0.2697 0.077 Uiso 1 1 calc R . . H27B H 0.7749 -0.1026 0.2425 0.077 Uiso 1 1 calc R . . H27A H 0.8772 -0.2733 0.2557 0.077 Uiso 1 1 calc R . . C28 C 0.6107(2) -0.1854(2) 0.32307(10) 0.0571(5) Uani 1 1 d . . . H28C H 0.637 -0.288 0.311 0.086 Uiso 1 1 calc R . . H28B H 0.5353 -0.1176 0.2972 0.086 Uiso 1 1 calc R . . H28A H 0.5582 -0.1721 0.3596 0.086 Uiso 1 1 calc R . . C29 C 0.83303(18) 0.15961(15) 0.40194(6) 0.0284(3) Uani 1 1 d . . . C30 C 0.92710(17) 0.23304(16) 0.37512(6) 0.0301(3) Uani 1 1 d . . . C31 C 0.9459(2) 0.35253(17) 0.40147(7) 0.0375(4) Uani 1 1 d . . . H31 H 1.0115 0.4015 0.3845 0.045 Uiso 1 1 calc R . . C32 C 0.8712(2) 0.40167(19) 0.45188(7) 0.0448(4) Uani 1 1 d . . . H32 H 0.8843 0.4844 0.4691 0.054 Uiso 1 1 calc R . . C33 C 0.7775(2) 0.32970(19) 0.47710(7) 0.0421(4) Uani 1 1 d . . . H33 H 0.7253 0.3648 0.5115 0.051 Uiso 1 1 calc R . . C34 C 0.75758(19) 0.20729(17) 0.45341(6) 0.0334(4) Uani 1 1 d . . . C35 C 1.00764(19) 0.17783(18) 0.31981(7) 0.0354(4) Uani 1 1 d . . . H35 H 0.9353 0.134 0.3009 0.042 Uiso 1 1 calc R . . C36 C 1.0240(2) 0.2999(2) 0.28247(7) 0.0475(4) Uani 1 1 d . . . H36C H 0.9143 0.3739 0.2757 0.071 Uiso 1 1 calc R . . H36B H 1.0764 0.2564 0.2476 0.071 Uiso 1 1 calc R . . H36A H 1.0918 0.3476 0.3002 0.071 Uiso 1 1 calc R . . C37 C 1.1746(2) 0.0531(2) 0.32710(8) 0.0507(5) Uani 1 1 d . . . H37C H 1.2473 0.0905 0.3474 0.076 Uiso 1 1 calc R . . H37B H 1.2245 0.0176 0.2911 0.076 Uiso 1 1 calc R . . H37A H 1.159 -0.0288 0.3475 0.076 Uiso 1 1 calc R . . C38 C 0.6635(2) 0.12198(19) 0.48266(7) 0.0406(4) Uani 1 1 d . . . H38 H 0.6112 0.0817 0.4539 0.049 Uiso 1 1 calc R . . C39 C 0.7843(3) -0.0110(3) 0.51313(9) 0.0699(7) Uani 1 1 d . . . H39C H 0.8634 -0.0768 0.4868 0.105 Uiso 1 1 calc R . . H39B H 0.7232 -0.0655 0.532 0.105 Uiso 1 1 calc R . . H39A H 0.8437 0.0243 0.54 0.105 Uiso 1 1 calc R . . C40 C 0.5263(3) 0.2172(3) 0.52081(9) 0.0679(6) Uani 1 1 d . . . H40C H 0.4657 0.1573 0.5362 0.102 Uiso 1 1 calc R . . H40B H 0.4508 0.3008 0.5003 0.102 Uiso 1 1 calc R . . H40A H 0.5739 0.2548 0.5506 0.102 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 N1 0.0255(7) 0.0486(8) 0.0292(7) -0.0073(6) -0.0009(5) -0.0131(6) N2 0.0397(8) 0.0235(7) 0.0487(8) -0.0006(6) -0.0186(7) -0.0110(6) N3 0.0316(7) 0.0340(7) 0.0270(7) -0.0035(5) -0.0015(5) -0.0133(5) N4 0.0321(7) 0.0253(6) 0.0343(7) 0.0032(5) -0.0041(6) -0.0094(5) C1 0.0246(7) 0.0286(8) 0.0275(8) -0.0031(6) -0.0032(6) -0.0076(6) C2 0.0257(7) 0.0223(7) 0.0305(8) -0.0013(6) -0.0055(6) -0.0075(6) C3 0.0310(8) 0.0422(9) 0.0292(8) -0.0005(7) -0.0034(6) -0.0102(7) C4 0.0402(9) 0.0406(10) 0.0425(10) -0.0164(7) -0.0017(8) -0.0031(7) C5 0.0447(10) 0.0269(8) 0.0530(11) -0.0046(7) -0.0087(8) 0.0005(7) C6 0.0428(9) 0.0289(8) 0.0395(9) 0.0060(7) -0.0099(7) -0.0097(7) C7 0.0309(8) 0.0246(7) 0.0278(8) 0.0003(6) -0.0010(6) -0.0096(6) C8 0.0339(8) 0.0418(9) 0.0311(8) -0.0015(7) 0.0031(7) -0.0158(7) C9 0.0833(16) 0.0767(15) 0.0604(13) -0.0107(11) 0.0196(11) -0.0559(13) C10 0.0418(11) 0.0894(16) 0.0513(12) 0.0076(11) 0.0128(9) 0.0014(10) C11 0.0518(11) 0.0672(13) 0.0353(9) -0.0080(8) 0.0102(8) -0.0282(10) C12 0.0299(8) 0.0402(9) 0.0256(8) -0.0046(6) 0.0016(6) -0.0155(7) C13 0.0358(9) 0.0394(9) 0.0336(8) -0.0065(7) 0.0007(7) -0.0156(7) C14 0.0469(10) 0.0444(10) 0.0384(9) -0.0119(7) -0.0001(8) -0.0214(8) C15 0.0481(10) 0.0599(12) 0.0315(9) -0.0091(8) -0.0060(8) -0.0251(9) C16 0.0425(10) 0.0521(11) 0.0337(9) 0.0029(7) -0.0080(7) -0.0189(8) C17 0.0350(8) 0.0427(9) 0.0304(8) -0.0002(7) -0.0023(7) -0.0187(7) C18 0.0513(11) 0.0350(9) 0.0520(11) -0.0038(8) -0.0121(8) -0.0158(8) C19 0.101(2) 0.104(2) 0.0601(15) 0.0416(14) 0.0228(14) 0.0103(16) C20 0.0918(18) 0.0466(13) 0.0883(18) 0.0054(12) 0.0217(14) 0.0000(12) C21 0.0428(10) 0.0391(9) 0.0506(10) 0.0063(8) -0.0139(8) -0.0186(8) C22 0.123(2) 0.0639(14) 0.0844(17) 0.0332(12) -0.0515(16) -0.0567(15) C23 0.0720(15) 0.0497(13) 0.121(2) -0.0328(13) 0.0233(15) -0.0218(11) C24 0.0262(7) 0.0233(7) 0.0278(7) 0.0013(6) 0.0037(6) -0.0087(6) C25 0.0376(9) 0.0230(8) 0.0386(9) -0.0032(6) 0.0044(7) -0.0098(6) C26 0.0733(13) 0.0231(9) 0.0586(12) 0.0033(8) -0.0049(10) -0.0046(8) C27 0.0653(12) 0.0370(10) 0.0459(11) -0.0108(8) 0.0147(9) -0.0117(9) C28 0.0565(12) 0.0348(10) 0.0872(15) -0.0139(9) 0.0089(11) -0.0253(9) C29 0.0281(7) 0.0250(7) 0.0307(8) 0.0045(6) -0.0101(6) -0.0073(6) C30 0.0261(7) 0.0278(8) 0.0351(8) 0.0059(6) -0.0085(6) -0.0076(6) C31 0.0363(9) 0.0321(8) 0.0479(10) 0.0063(7) -0.0095(7) -0.0165(7) C32 0.0525(11) 0.0366(9) 0.0492(11) -0.0062(8) -0.0092(8) -0.0201(8) C33 0.0499(10) 0.0445(10) 0.0336(9) -0.0062(7) -0.0034(8) -0.0186(8) C34 0.0348(8) 0.0364(8) 0.0292(8) 0.0033(6) -0.0083(7) -0.0127(7) C35 0.0305(8) 0.0401(9) 0.0374(9) 0.0037(7) -0.0024(7) -0.0149(7) C36 0.0465(10) 0.0601(12) 0.0439(10) 0.0110(8) -0.0047(8) -0.0288(9) C37 0.0359(9) 0.0560(12) 0.0506(11) -0.0013(9) 0.0032(8) -0.0052(8) C38 0.0445(10) 0.0503(10) 0.0315(9) 0.0051(7) -0.0046(7) -0.0225(8) C39 0.0756(15) 0.0827(16) 0.0659(14) 0.0429(12) -0.0259(12) -0.0456(13) C40 0.0829(16) 0.0860(16) 0.0492(12) -0.0192(11) 0.0255(11) -0.0491(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1 C7 1.3755(19) . ? N1 C1 1.4566(19) . ? N2 C24 1.3609(19) . ? N2 C2 1.4597(18) . ? N3 C7 1.2743(19) . ? N3 C12 1.4092(19) . ? N4 C24 1.2717(19) . ? N4 C29 1.4123(19) . ? C1 C2 1.5256(19) . ? C1 C6 1.527(2) . ? C2 C3 1.522(2) . ? C3 C4 1.524(2) . ? C4 C5 1.519(2) . ? C5 C6 1.517(2) . ? C7 C8 1.546(2) . ? C8 C10 1.527(3) . ? C8 C11 1.528(2) . ? C8 C9 1.537(2) . ? C12 C13 1.406(2) . ? C12 C17 1.409(2) . ? C13 C14 1.393(2) . ? C13 C18 1.517(2) . ? C14 C15 1.377(3) . ? C15 C16 1.382(2) . ? C16 C17 1.394(2) . ? C17 C21 1.520(2) . ? C18 C20 1.510(3) . ? C18 C19 1.511(3) . ? C21 C23 1.519(3) . ? C21 C22 1.523(3) . ? C24 C25 1.539(2) . ? C25 C26 1.521(2) . ? C25 C28 1.527(2) . ? C25 C27 1.531(2) . ? C29 C34 1.405(2) . ? C29 C30 1.410(2) . ? C30 C31 1.390(2) . ? C30 C35 1.515(2) . ? C31 C32 1.382(2) . ? C32 C33 1.381(3) . ? C33 C34 1.390(2) . ? C34 C38 1.520(2) . ? C35 C37 1.529(2) . ? C35 C36 1.530(2) . ? C38 C40 1.519(3) . ? C38 C39 1.534(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 C7 N1 C1 122.58(13) . . ? C24 N2 C2 129.08(13) . . ? C7 N3 C12 129.97(13) . . ? C24 N4 C29 128.56(12) . . ? N1 C1 C2 110.98(11) . . ? N1 C1 C6 110.68(13) . . ? C2 C1 C6 110.65(12) . . ? N2 C2 C3 112.33(13) . . ? N2 C2 C1 109.31(12) . . ? C3 C2 C1 110.21(11) . . ? C2 C3 C4 111.54(13) . . ? C5 C4 C3 111.02(13) . . ? C6 C5 C4 111.07(13) . . ? C5 C6 C1 112.47(14) . . ? N3 C7 N1 116.45(13) . . ? N3 C7 C8 130.64(13) . . ? N1 C7 C8 112.91(12) . . ? C10 C8 C11 108.10(15) . . ? C10 C8 C9 109.66(17) . . ? C11 C8 C9 106.94(15) . . ? C10 C8 C7 109.74(13) . . ? C11 C8 C7 113.84(13) . . ? C9 C8 C7 108.48(14) . . ? C13 C12 C17 120.70(14) . . ? C13 C12 N3 120.08(14) . . ? C17 C12 N3 118.71(14) . . ? C14 C13 C12 118.59(15) . . ? C14 C13 C18 120.56(15) . . ? C12 C13 C18 120.81(14) . . ? C15 C14 C13 121.35(16) . . ? C14 C15 C16 119.63(15) . . ? C15 C16 C17 121.57(16) . . ? C16 C17 C12 118.12(15) . . ? C16 C17 C21 121.48(15) . . ? C12 C17 C21 120.37(13) . . ? C20 C18 C19 108.82(19) . . ? C20 C18 C13 114.16(17) . . ? C19 C18 C13 110.03(16) . . ? C23 C21 C17 110.26(15) . . ? C23 C21 C22 112.0(2) . . ? C17 C21 C22 113.50(16) . . ? N4 C24 N2 128.50(13) . . ? N4 C24 C25 117.22(13) . . ? N2 C24 C25 114.26(13) . . ? C26 C25 C28 108.57(15) . . ? C26 C25 C27 108.92(14) . . ? C28 C25 C27 109.70(15) . . ? C26 C25 C24 109.82(13) . . ? C28 C25 C24 111.84(13) . . ? C27 C25 C24 107.95(13) . . ? C34 C29 C30 121.14(14) . . ? C34 C29 N4 119.26(13) . . ? C30 C29 N4 119.16(13) . . ? C31 C30 C29 118.14(14) . . ? C31 C30 C35 122.17(14) . . ? C29 C30 C35 119.66(13) . . ? C32 C31 C30 121.43(15) . . ? C33 C32 C31 119.54(15) . . ? C32 C33 C34 121.67(16) . . ? C33 C34 C29 118.05(15) . . ? C33 C34 C38 121.79(15) . . ? C29 C34 C38 120.11(14) . . ? C30 C35 C37 110.35(13) . . ? C30 C35 C36 113.99(14) . . ? C37 C35 C36 111.04(14) . . ? C40 C38 C34 113.67(15) . . ? C40 C38 C39 111.22(17) . . ? C34 C38 C39 109.74(14) . . ? #===END data_nov2104 _database_code_depnum_ccdc_archive 'CCDC 284725' _audit_creation_date 2004-11-22T13:30:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H52 N4' _chemical_formula_sum 'C34 H52 N4' _chemical_formula_weight 516.8 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 16.8665(5) _cell_length_b 13.1292(5) _cell_length_c 17.0086(6) _cell_angle_alpha 90 _cell_angle_beta 117.644(2) _cell_angle_gamma 90 _cell_volume 3336.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 11907 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.4 _exptl_crystal_density_diffrn 1.029 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.06 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.648035E-1 _diffrn_orient_matrix_ub_12 0.62701E-2 _diffrn_orient_matrix_ub_13 0.159359E-1 _diffrn_orient_matrix_ub_21 -0.160154E-1 _diffrn_orient_matrix_ub_22 0.440838E-1 _diffrn_orient_matrix_ub_23 -0.532032E-1 _diffrn_orient_matrix_ub_31 0.48499E-2 _diffrn_orient_matrix_ub_32 0.617947E-1 _diffrn_orient_matrix_ub_33 0.363378E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_unetI/netI 0.0473 _diffrn_reflns_number 19572 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 26.04 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _reflns_number_total 6512 _reflns_number_gt 4076 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Very weak diffraction at higher angle. The H atoms on N1 and N2 were refined; other H atoms were in riding mode. Disorder in both tButyl groups; lower occupancy sites were left isotropic. 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^)+(0.0830P)^2^+0.9090P] 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_number_reflns 6512 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1115 _refine_ls_R_factor_gt 0.0675 _refine_ls_wR_factor_ref 0.1922 _refine_ls_wR_factor_gt 0.1637 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.204 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.029 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' 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 N1 N 0.23614(11) 0.74045(12) 0.07472(11) 0.0501(4) Uani 1 1 d . . . H1N H 0.2835(15) 0.7441(16) 0.1290(15) 0.065(6) Uiso 1 1 d . . . N2 N 0.24101(13) 0.95279(13) 0.03142(14) 0.0617(5) Uani 1 1 d . . . H2N H 0.2023(16) 0.9441(17) -0.0240(16) 0.070(7) Uiso 1 1 d . . . N3 N 0.15831(12) 0.61903(13) -0.03815(12) 0.0648(5) Uani 1 1 d . . . N4 N 0.36210(15) 1.06023(17) 0.12314(19) 0.0890(7) Uani 1 1 d . . . C1 C 0.16561(12) 0.81283(13) 0.06450(12) 0.0456(4) Uani 1 1 d . . . H1 H 0.119 0.8132 0.0009 0.055 Uiso 1 1 calc R . . C2 C 0.20439(13) 0.91938(14) 0.08952(13) 0.0510(5) Uani 1 1 d . . . H2 H 0.2537 0.9181 0.1519 0.061 Uiso 1 1 calc R . . C3 C 0.13187(15) 0.99327(16) 0.08434(15) 0.0666(6) Uani 1 1 d . . . H3B H 0.1587 1.0616 0.1037 0.08 Uiso 1 1 calc R . . H3A H 0.085 0.9987 0.0218 0.08 Uiso 1 1 calc R . . C4 C 0.08906(17) 0.9603(2) 0.14119(17) 0.0803(7) Uani 1 1 d . . . H4B H 0.1345 0.9607 0.2045 0.096 Uiso 1 1 calc R . . H4A H 0.0412 1.0089 0.1336 0.096 Uiso 1 1 calc R . . C5 C 0.04999(16) 0.8546(2) 0.11538(17) 0.0762(7) Uani 1 1 d . . . H5B H 0.0003 0.8555 0.054 0.091 Uiso 1 1 calc R . . H5A H 0.0257 0.8322 0.1555 0.091 Uiso 1 1 calc R . . C6 C 0.12178(14) 0.78061(17) 0.12132(15) 0.0627(6) Uani 1 1 d . . . H6B H 0.0947 0.7123 0.1021 0.075 Uiso 1 1 calc R . . H6A H 0.1683 0.7753 0.184 0.075 Uiso 1 1 calc R . . C7 C 0.22013(13) 0.64431(15) 0.03863(13) 0.0529(5) Uani 1 1 d . A . C8 C 0.28496(15) 0.56187(16) 0.09735(15) 0.0651(6) Uani 1 1 d . . . C12 C 0.29864(17) 1.03306(17) 0.04719(19) 0.0729(7) Uani 1 1 d . B . C13 C 0.2873(2) 1.0938(2) -0.0348(2) 0.0961(9) Uani 1 1 d . . . C17 C 0.10374(14) 0.69069(16) -0.10310(13) 0.0596(6) Uani 1 1 d . . . C18 C 0.14009(15) 0.75300(17) -0.14479(13) 0.0637(6) Uani 1 1 d . . . C19 C 0.08360(19) 0.81901(18) -0.21090(14) 0.0737(7) Uani 1 1 d . . . H19 H 0.1087 0.8626 -0.2381 0.088 Uiso 1 1 calc R . . C20 C -0.00737(19) 0.8242(2) -0.23888(15) 0.0766(7) Uani 1 1 d . . . C21 C -0.04150(16) 0.7596(2) -0.19869(15) 0.0775(7) Uani 1 1 d . . . H21 H -0.1041 0.761 -0.2175 0.093 Uiso 1 1 calc R . . C22 C 0.01147(15) 0.69190(18) -0.13137(15) 0.0689(6) Uani 1 1 d . . . C23 C 0.23844(16) 0.7476(2) -0.11954(16) 0.0809(7) Uani 1 1 d . . . H23C H 0.2547 0.677 -0.1242 0.121 Uiso 1 1 calc R . . H23B H 0.2738 0.7715 -0.0584 0.121 Uiso 1 1 calc R . . H23A H 0.2507 0.7908 -0.1597 0.121 Uiso 1 1 calc R . . C24 C -0.0676(2) 0.8944(2) -0.31344(17) 0.1116(11) Uani 1 1 d . . . H24F H -0.0501 0.9653 -0.296 0.167 Uiso 0.5 1 calc PR . . H24E H -0.1298 0.8844 -0.3257 0.167 Uiso 0.5 1 calc PR . . H24D H -0.0617 0.8788 -0.3669 0.167 Uiso 0.5 1 calc PR . . H24C H -0.111 0.8537 -0.3631 0.167 Uiso 0.5 1 calc PR . . H24B H -0.0313 0.9346 -0.3333 0.167 Uiso 0.5 1 calc PR . . H24A H -0.0994 0.9402 -0.2922 0.167 Uiso 0.5 1 calc PR . . C25 C -0.02907(18) 0.6230(2) -0.0896(2) 0.1036(10) Uani 1 1 d . . . H25C H -0.0216 0.6531 -0.0339 0.155 Uiso 1 1 calc R . . H25B H 0.0009 0.5566 -0.0775 0.155 Uiso 1 1 calc R . . H25A H -0.093 0.6141 -0.1302 0.155 Uiso 1 1 calc R . . C26 C 0.38808(16) 1.0031(2) 0.2018(2) 0.0820(8) Uani 1 1 d . . . C27 C 0.43514(15) 0.9120(2) 0.21332(18) 0.0781(7) Uani 1 1 d . . . C28 C 0.46081(16) 0.8577(3) 0.2918(2) 0.0938(9) Uani 1 1 d . . . H28 H 0.4917 0.795 0.2993 0.113 Uiso 1 1 calc R . . C29 C 0.4432(2) 0.8909(4) 0.3588(2) 0.1116(12) Uani 1 1 d . . . C30 C 0.4015(2) 0.9824(4) 0.3479(2) 0.1191(14) Uani 1 1 d . . . H30 H 0.3905 1.0071 0.3944 0.143 Uiso 1 1 calc R . . C31 C 0.37409(18) 1.0422(3) 0.2714(2) 0.1023(11) Uani 1 1 d . . . C32 C 0.45849(18) 0.8742(2) 0.14326(19) 0.0896(8) Uani 1 1 d . . . H32C H 0.4872 0.929 0.1266 0.134 Uiso 1 1 calc R . . H32B H 0.4038 0.8526 0.091 0.134 Uiso 1 1 calc R . . H32A H 0.4996 0.8163 0.1665 0.134 Uiso 1 1 calc R . . C33 C 0.4714(2) 0.8309(4) 0.4432(2) 0.164(2) Uani 1 1 d . . . H33F H 0.441 0.7648 0.4292 0.247 Uiso 0.5 1 calc PR . . H33E H 0.4553 0.8686 0.4835 0.247 Uiso 0.5 1 calc PR . . H33D H 0.5364 0.8203 0.4718 0.247 Uiso 0.5 1 calc PR . . H33C H 0.5141 0.871 0.4938 0.247 Uiso 0.5 1 calc PR . . H33B H 0.4998 0.7672 0.4395 0.247 Uiso 0.5 1 calc PR . . H33A H 0.4188 0.8155 0.4512 0.247 Uiso 0.5 1 calc PR . . C34 C 0.3298(2) 1.1448(3) 0.2607(3) 0.1454(16) Uani 1 1 d . . . H34C H 0.3528 1.1781 0.3187 0.218 Uiso 1 1 calc R . . H34B H 0.265 1.1357 0.2356 0.218 Uiso 1 1 calc R . . H34A H 0.343 1.1873 0.2208 0.218 Uiso 1 1 calc R . . C9 C 0.38122(19) 0.5972(3) 0.1306(3) 0.1029(15) Uani 0.875(6) 1 d P A 1 H9A H 0.3907 0.6607 0.1641 0.154 Uiso 0.875(6) 1 calc PR A 1 H9B H 0.3927 0.609 0.0798 0.154 Uiso 0.875(6) 1 calc PR A 1 H9C H 0.4222 0.5448 0.1691 0.154 Uiso 0.875(6) 1 calc PR A 1 C10 C 0.2689(3) 0.5445(3) 0.1780(3) 0.1098(16) Uani 0.875(6) 1 d P A 1 H10A H 0.2776 0.6087 0.2104 0.165 Uiso 0.875(6) 1 calc PR A 1 H10B H 0.3112 0.4935 0.2171 0.165 Uiso 0.875(6) 1 calc PR A 1 H10C H 0.2075 0.5203 0.1579 0.165 Uiso 0.875(6) 1 calc PR A 1 C11 C 0.2701(4) 0.4636(3) 0.0469(3) 0.143(3) Uani 0.875(6) 1 d P A 1 H11A H 0.2079 0.4417 0.0252 0.215 Uiso 0.875(6) 1 calc PR A 1 H11B H 0.3104 0.4112 0.0863 0.215 Uiso 0.875(6) 1 calc PR A 1 H11C H 0.2823 0.4739 -0.0035 0.215 Uiso 0.875(6) 1 calc PR A 1 C14 C 0.2809(5) 1.2055(3) -0.0170(4) 0.148(2) Uani 0.798(7) 1 d P B 1 H14C H 0.2297 1.2163 -0.0055 0.222 Uiso 0.798(7) 1 calc PR B 1 H14B H 0.2728 1.2455 -0.0689 0.222 Uiso 0.798(7) 1 calc PR B 1 H14A H 0.3359 1.227 0.0348 0.222 Uiso 0.798(7) 1 calc PR B 1 C15 C 0.3672(4) 1.0749(5) -0.0503(5) 0.158(3) Uani 0.798(7) 1 d P B 1 H15C H 0.3615 1.1155 -0.101 0.236 Uiso 0.798(7) 1 calc PR B 1 H15B H 0.3699 1.0025 -0.0627 0.236 Uiso 0.798(7) 1 calc PR B 1 H15A H 0.422 1.0944 0.0028 0.236 Uiso 0.798(7) 1 calc PR B 1 C16 C 0.2031(4) 1.0652(4) -0.1220(3) 0.155(3) Uani 0.798(7) 1 d P B 1 H16C H 0.1493 1.0783 -0.1153 0.232 Uiso 0.798(7) 1 calc PR B 1 H16B H 0.2056 0.9928 -0.1348 0.232 Uiso 0.798(7) 1 calc PR B 1 H16A H 0.2012 1.1063 -0.1709 0.232 Uiso 0.798(7) 1 calc PR B 1 C14A C 0.3661(12) 1.1737(14) -0.0011(11) 0.110(6) Uiso 0.202(7) 1 d P B 2 H14F H 0.4236 1.1377 0.0249 0.165 Uiso 0.202(7) 1 calc PR B 2 H14E H 0.363 1.2177 0.0439 0.165 Uiso 0.202(7) 1 calc PR B 2 H14D H 0.3608 1.2154 -0.0511 0.165 Uiso 0.202(7) 1 calc PR B 2 C15A C 0.2941(16) 1.0245(16) -0.0962(13) 0.119(7) Uiso 0.202(7) 1 d P B 2 H15F H 0.3532 0.9922 -0.0685 0.178 Uiso 0.202(7) 1 calc PR B 2 H15E H 0.2862 1.0618 -0.1493 0.178 Uiso 0.202(7) 1 calc PR B 2 H15D H 0.2477 0.9722 -0.1129 0.178 Uiso 0.202(7) 1 calc PR B 2 C16A C 0.1985(17) 1.157(2) -0.0588(17) 0.152(9) Uiso 0.202(7) 1 d P B 2 H16F H 0.1849 1.2003 -0.1105 0.227 Uiso 0.202(7) 1 calc PR B 2 H16E H 0.2072 1.1998 -0.0082 0.227 Uiso 0.202(7) 1 calc PR B 2 H16D H 0.1487 1.11 -0.0725 0.227 Uiso 0.202(7) 1 calc PR B 2 C9A C 0.3610(19) 0.598(2) 0.1865(18) 0.100(9) Uiso 0.125(6) 1 d P A 2 H9A1 H 0.3962 0.6503 0.1759 0.15 Uiso 0.125(6) 1 calc PR A 2 H9A2 H 0.3997 0.54 0.2174 0.15 Uiso 0.125(6) 1 calc PR A 2 H9A3 H 0.3355 0.6262 0.2232 0.15 Uiso 0.125(6) 1 calc PR A 2 C10A C 0.2333(16) 0.488(2) 0.1167(18) 0.087(8) Uiso 0.125(6) 1 d P A 2 H10D H 0.2731 0.4335 0.154 0.13 Uiso 0.125(6) 1 calc PR A 2 H10E H 0.1877 0.4581 0.0612 0.13 Uiso 0.125(6) 1 calc PR A 2 H10F H 0.2042 0.5207 0.1482 0.13 Uiso 0.125(6) 1 calc PR A 2 C11A C 0.323(3) 0.508(3) 0.038(2) 0.134(13) Uiso 0.125(6) 1 d P A 2 H11D H 0.3609 0.5561 0.0265 0.201 Uiso 0.125(6) 1 calc PR A 2 H11E H 0.2737 0.4854 -0.0177 0.201 Uiso 0.125(6) 1 calc PR A 2 H11F H 0.3596 0.4488 0.0705 0.201 Uiso 0.125(6) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0433(9) 0.0507(9) 0.0472(9) -0.0009(7) 0.0133(8) 0.0046(7) N2 0.0696(12) 0.0554(11) 0.0595(12) -0.0051(9) 0.0294(10) -0.0127(9) N3 0.0629(11) 0.0539(10) 0.0585(11) -0.0053(8) 0.0121(9) 0.0033(9) N4 0.0755(14) 0.0752(14) 0.116(2) -0.0273(14) 0.0441(14) -0.0259(12) C1 0.0418(9) 0.0469(10) 0.0412(10) 0.0026(8) 0.0134(8) 0.0055(8) C2 0.0489(10) 0.0524(11) 0.0461(10) -0.0032(9) 0.0171(9) 0.0007(9) C3 0.0685(14) 0.0523(12) 0.0723(15) -0.0094(10) 0.0269(12) 0.0054(11) C4 0.0764(16) 0.0970(19) 0.0698(15) -0.0035(13) 0.0357(13) 0.0271(14) C5 0.0666(14) 0.0911(18) 0.0845(17) 0.0268(14) 0.0465(13) 0.0242(13) C6 0.0580(12) 0.0690(13) 0.0657(13) 0.0184(11) 0.0326(11) 0.0124(11) C7 0.0500(11) 0.0485(11) 0.0544(12) 0.0004(9) 0.0192(10) 0.0036(9) C8 0.0635(13) 0.0535(12) 0.0658(14) 0.0057(10) 0.0194(11) 0.0133(10) C12 0.0771(16) 0.0525(13) 0.0965(19) -0.0088(12) 0.0466(15) -0.0095(12) C13 0.114(2) 0.0642(16) 0.127(3) 0.0151(16) 0.070(2) -0.0121(16) C17 0.0608(12) 0.0554(12) 0.0462(11) -0.0112(9) 0.0108(10) 0.0032(10) C18 0.0721(14) 0.0699(14) 0.0441(11) -0.0102(10) 0.0228(10) 0.0068(12) C19 0.0992(19) 0.0750(15) 0.0468(12) -0.0026(11) 0.0339(13) 0.0142(14) C20 0.0916(18) 0.0768(16) 0.0470(13) -0.0067(11) 0.0201(13) 0.0248(14) C21 0.0615(14) 0.0869(17) 0.0583(14) -0.0147(13) 0.0061(11) 0.0138(13) C22 0.0605(13) 0.0671(14) 0.0592(13) -0.0105(11) 0.0109(11) -0.0048(11) C23 0.0800(16) 0.106(2) 0.0604(14) -0.0038(13) 0.0359(12) 0.0055(15) C24 0.133(3) 0.121(2) 0.0601(16) 0.0143(16) 0.0274(17) 0.057(2) C25 0.0659(16) 0.105(2) 0.114(2) 0.0068(18) 0.0200(16) -0.0172(15) C26 0.0537(13) 0.097(2) 0.0866(19) -0.0350(16) 0.0255(13) -0.0259(14) C27 0.0468(12) 0.106(2) 0.0753(17) -0.0225(15) 0.0230(12) -0.0203(13) C28 0.0470(13) 0.137(3) 0.085(2) -0.0156(18) 0.0197(13) -0.0144(15) C29 0.0549(16) 0.197(4) 0.074(2) -0.026(2) 0.0222(15) -0.021(2) C30 0.0632(18) 0.209(4) 0.080(2) -0.057(3) 0.0294(17) -0.034(2) C31 0.0595(15) 0.135(3) 0.106(3) -0.066(2) 0.0333(16) -0.0307(17) C32 0.0729(16) 0.105(2) 0.098(2) -0.0144(16) 0.0457(15) -0.0024(15) C33 0.095(2) 0.306(6) 0.080(2) 0.010(3) 0.0298(19) -0.011(3) C34 0.106(2) 0.154(3) 0.170(4) -0.097(3) 0.059(3) -0.023(2) C9 0.0586(17) 0.091(2) 0.141(3) 0.029(2) 0.0312(19) 0.0286(16) C10 0.132(3) 0.097(3) 0.102(3) 0.049(2) 0.056(3) 0.038(2) C11 0.166(5) 0.064(2) 0.116(3) -0.016(2) -0.006(3) 0.052(3) C14 0.204(7) 0.066(3) 0.204(6) 0.027(3) 0.121(5) 0.013(3) C15 0.180(6) 0.164(5) 0.197(6) 0.060(5) 0.145(5) 0.041(5) C16 0.175(5) 0.150(4) 0.104(4) 0.063(3) 0.036(3) -0.045(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N1 C7 1.375(2) . ? N1 C1 1.468(2) . ? N2 C12 1.373(3) . ? N2 C2 1.455(3) . ? N3 C7 1.280(2) . ? N3 C17 1.417(3) . ? N4 C12 1.288(3) . ? N4 C26 1.414(4) . ? C1 C2 1.519(3) . ? C1 C6 1.524(3) . ? C2 C3 1.531(3) . ? C3 C4 1.514(3) . ? C4 C5 1.511(4) . ? C5 C6 1.519(3) . ? C7 C8 1.533(3) . ? C8 C10A 1.44(2) . ? C8 C11 1.505(4) . ? C8 C9 1.523(4) . ? C8 C10 1.533(4) . ? C8 C9A 1.54(3) . ? C8 C11A 1.59(4) . ? C12 C13 1.539(4) . ? C13 C15A 1.429(19) . ? C13 C15 1.508(6) . ? C13 C14 1.511(5) . ? C13 C16 1.550(6) . ? C13 C14A 1.578(17) . ? C13 C16A 1.59(2) . ? C17 C18 1.397(3) . ? C17 C22 1.400(3) . ? C18 C19 1.389(3) . ? C18 C23 1.510(3) . ? C19 C20 1.381(4) . ? C20 C21 1.373(4) . ? C20 C24 1.514(3) . ? C21 C22 1.397(3) . ? C22 C25 1.497(4) . ? C26 C27 1.397(4) . ? C26 C31 1.408(4) . ? C27 C28 1.394(4) . ? C27 C32 1.502(4) . ? C28 C29 1.376(4) . ? C29 C30 1.360(5) . ? C29 C33 1.508(5) . ? C30 C31 1.401(5) . ? C31 C34 1.510(5) . ? 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 124.11(16) . . ? C12 N2 C2 125.7(2) . . ? C7 N3 C17 123.36(17) . . ? C12 N4 C26 123.4(2) . . ? N1 C1 C2 110.05(14) . . ? N1 C1 C6 110.49(15) . . ? C2 C1 C6 110.52(16) . . ? N2 C2 C1 110.53(16) . . ? N2 C2 C3 110.45(17) . . ? C1 C2 C3 109.79(16) . . ? C4 C3 C2 112.77(18) . . ? C5 C4 C3 110.49(19) . . ? C4 C5 C6 109.95(19) . . ? C5 C6 C1 112.74(17) . . ? N3 C7 N1 126.29(18) . . ? N3 C7 C8 118.59(18) . . ? N1 C7 C8 115.11(17) . . ? C10A C8 C11 65.9(11) . . ? C10A C8 C9 140.7(10) . . ? C11 C8 C9 109.9(3) . . ? C10A C8 C10 47.1(11) . . ? C11 C8 C10 109.3(3) . . ? C9 C8 C10 108.3(3) . . ? C10A C8 C7 107.6(10) . . ? C11 C8 C7 110.7(2) . . ? C9 C8 C7 110.0(2) . . ? C10 C8 C7 108.6(2) . . ? C10A C8 C9A 107.3(15) . . ? C7 C8 C9A 116.2(10) . . ? C10A C8 C11A 107.9(18) . . ? C7 C8 C11A 106.3(14) . . ? C9A C8 C11A 111.2(18) . . ? N4 C12 N2 126.3(2) . . ? N4 C12 C13 117.4(2) . . ? N2 C12 C13 116.2(2) . . ? C15A C13 C15 52.2(9) . . ? C15A C13 C14 143.3(9) . . ? C15 C13 C14 110.4(4) . . ? C15A C13 C12 108.3(8) . . ? C15 C13 C12 109.1(3) . . ? C14 C13 C12 108.2(3) . . ? C15A C13 C16 59.7(9) . . ? C15 C13 C16 106.8(4) . . ? C14 C13 C16 107.9(4) . . ? C12 C13 C16 114.5(2) . . ? C15A C13 C14A 110.4(12) . . ? C12 C13 C14A 106.6(7) . . ? C15A C13 C16A 122.0(14) . . ? C12 C13 C16A 102.1(9) . . ? C14A C13 C16A 106.3(13) . . ? C18 C17 C22 119.9(2) . . ? C18 C17 N3 120.33(19) . . ? C22 C17 N3 119.5(2) . . ? C19 C18 C17 118.6(2) . . ? C19 C18 C23 120.7(2) . . ? C17 C18 C23 120.7(2) . . ? C20 C19 C18 123.0(3) . . ? C21 C20 C19 116.9(2) . . ? C21 C20 C24 121.3(3) . . ? C19 C20 C24 121.7(3) . . ? C20 C21 C22 123.0(2) . . ? C21 C22 C17 118.4(2) . . ? C21 C22 C25 121.0(2) . . ? C17 C22 C25 120.7(2) . . ? C27 C26 C31 120.0(3) . . ? C27 C26 N4 119.5(2) . . ? C31 C26 N4 120.2(3) . . ? C28 C27 C26 118.4(3) . . ? C28 C27 C32 120.7(3) . . ? C26 C27 C32 120.8(3) . . ? C29 C28 C27 122.7(3) . . ? C30 C29 C28 117.6(4) . . ? C30 C29 C33 120.5(4) . . ? C28 C29 C33 121.9(4) . . ? C29 C30 C31 123.3(3) . . ? C30 C31 C26 117.7(3) . . ? C30 C31 C34 123.0(3) . . ? C26 C31 C34 119.4(4) . . ? #====END data_(13)-dec1804 _database_code_depnum_ccdc_archive 'CCDC 284726' _audit_creation_date 2004-12-13T12:46:34-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C42 H66 Li2 N4 O2, 0.5(C7 H8)' _chemical_formula_sum 'C45.5 H70 Li2 N4 O2' _chemical_formula_weight 718.93 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M I2cb _symmetry_space_group_name_Hall 'I -2a 2' _symmetry_Int_Tables_number 45 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, y, -z' 'x, -y, -z' 'x+1/2, -y, z' 'x+1/2, y+1/2, z+1/2' 'x+1, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' 'x+1, -y+1/2, z+1/2' _cell_length_a 18.1733(7) _cell_length_b 31.7551(6) _cell_length_c 14.7468(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 8510.3(5) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16285 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.122 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3144 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.067 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.210632E-1 _diffrn_orient_matrix_ub_12 0.14029E-2 _diffrn_orient_matrix_ub_13 -0.836348E-1 _diffrn_orient_matrix_ub_21 -0.507501E-1 _diffrn_orient_matrix_ub_22 -0.23945E-2 _diffrn_orient_matrix_ub_23 -0.250497E-1 _diffrn_orient_matrix_ub_31 -0.2932E-2 _diffrn_orient_matrix_ub_32 0.313685E-1 _diffrn_orient_matrix_ub_33 0.18283E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_av_unetI/netI 0.0418 _diffrn_reflns_number 24633 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 26.04 _diffrn_reflns_theta_full 26.04 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 6646 _reflns_number_gt 5844 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; The poorly defined toluene solvate molecule, disordered about a 2-fold axis, was included with a common isotropic U value, distance constraints, and H atoms omitted. 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^)+(0.1614P)^2^+14.5296P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6646 _refine_ls_number_parameters 469 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0894 _refine_ls_R_factor_gt 0.0804 _refine_ls_wR_factor_ref 0.2403 _refine_ls_wR_factor_gt 0.2305 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_diff_density_max 1.167 _refine_diff_density_min -0.779 _refine_diff_density_rms 0.073 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.63846(19) 0.60468(10) 0.2428(2) 0.0404(8) Uani 1 1 d . . . O2 O 0.2338(2) 0.59527(11) 0.3371(2) 0.0460(9) Uani 1 1 d . . . N1 N 0.48247(19) 0.62200(9) 0.3444(2) 0.0225(7) Uani 1 1 d . . . N2 N 0.38290(18) 0.60797(9) 0.2002(2) 0.0240(7) Uani 1 1 d . . . N3 N 0.37514(19) 0.64700(10) 0.4162(2) 0.0241(7) Uani 1 1 d . . . N4 N 0.48408(19) 0.63062(10) 0.1142(2) 0.0245(7) Uani 1 1 d . . . C1 C 0.4462(2) 0.58094(11) 0.3346(3) 0.0239(8) Uani 1 1 d . . . H1 H 0.3995 0.5814 0.3704 0.029 Uiso 1 1 calc R . . C2 C 0.4268(2) 0.57274(12) 0.2341(3) 0.0249(8) Uani 1 1 d . . . H2 H 0.4734 0.5712 0.1983 0.03 Uiso 1 1 calc R . . C3 C 0.3863(3) 0.53087(12) 0.2253(3) 0.0314(9) Uani 1 1 d . . . H3A H 0.3761 0.5251 0.1605 0.038 Uiso 1 1 calc R . . H3B H 0.3385 0.5327 0.2574 0.038 Uiso 1 1 calc R . . C4 C 0.4320(3) 0.49441(12) 0.2654(3) 0.0355(10) Uani 1 1 d . . . H4A H 0.4029 0.4681 0.2626 0.043 Uiso 1 1 calc R . . H4B H 0.4769 0.4904 0.2285 0.043 Uiso 1 1 calc R . . C5 C 0.4537(3) 0.50310(12) 0.3633(3) 0.0316(9) Uani 1 1 d . . . H5A H 0.4857 0.4801 0.3856 0.038 Uiso 1 1 calc R . . H5B H 0.409 0.5039 0.4017 0.038 Uiso 1 1 calc R . . C6 C 0.4945(2) 0.54525(11) 0.3706(3) 0.0265(8) Uani 1 1 d . . . H6A H 0.5073 0.5508 0.4348 0.032 Uiso 1 1 calc R . . H6B H 0.5408 0.5439 0.3352 0.032 Uiso 1 1 calc R . . C7 C 0.4463(2) 0.65118(11) 0.3906(2) 0.0233(8) Uani 1 1 d . . . C8 C 0.4898(2) 0.69341(11) 0.4035(2) 0.0255(8) Uani 1 1 d . . . C9 C 0.5506(3) 0.69753(13) 0.3332(3) 0.0319(9) Uani 1 1 d . . . H9A H 0.5772 0.724 0.3429 0.048 Uiso 1 1 calc R . . H9B H 0.529 0.6974 0.2723 0.048 Uiso 1 1 calc R . . H9C H 0.5848 0.6738 0.3391 0.048 Uiso 1 1 calc R . . C10 C 0.4371(2) 0.73123(12) 0.3908(3) 0.0314(9) Uani 1 1 d . . . H10A H 0.4166 0.7306 0.3293 0.047 Uiso 1 1 calc R . . H10B H 0.4643 0.7575 0.3997 0.047 Uiso 1 1 calc R . . H10C H 0.3971 0.7295 0.4351 0.047 Uiso 1 1 calc R . . C11 C 0.5263(3) 0.69600(14) 0.4977(3) 0.0362(10) Uani 1 1 d . . . H11A H 0.4883 0.6953 0.5448 0.054 Uiso 1 1 calc R . . H11B H 0.5542 0.7223 0.5026 0.054 Uiso 1 1 calc R . . H11C H 0.5597 0.672 0.5057 0.054 Uiso 1 1 calc R . . C12 C 0.3485(2) 0.66214(11) 0.4999(3) 0.0238(8) Uani 1 1 d . . . C13 C 0.3779(2) 0.64681(12) 0.5820(3) 0.0282(9) Uani 1 1 d . . . C14 C 0.3509(3) 0.66192(13) 0.6647(3) 0.0301(9) Uani 1 1 d . . . H14 H 0.3729 0.6524 0.7194 0.036 Uiso 1 1 calc R . . C15 C 0.2927(3) 0.69056(12) 0.6695(3) 0.0312(9) Uani 1 1 d . . . C16 C 0.2600(2) 0.70219(12) 0.5878(3) 0.0302(9) Uani 1 1 d . . . H16 H 0.2185 0.7204 0.5893 0.036 Uiso 1 1 calc R . . C17 C 0.2854(2) 0.68840(12) 0.5043(3) 0.0270(9) Uani 1 1 d . . . C18 C 0.4331(3) 0.61148(14) 0.5823(3) 0.0349(10) Uani 1 1 d . . . H18A H 0.4786 0.6209 0.5529 0.052 Uiso 1 1 calc R . . H18B H 0.413 0.5873 0.5493 0.052 Uiso 1 1 calc R . . H18C H 0.4437 0.6032 0.645 0.052 Uiso 1 1 calc R . . C19 C 0.2653(3) 0.70613(16) 0.7595(3) 0.0457(12) Uani 1 1 d . . . H19A H 0.3052 0.7207 0.7913 0.069 Uiso 0.5 1 calc PR . . H19B H 0.2485 0.6822 0.796 0.069 Uiso 0.5 1 calc PR . . H19C H 0.2243 0.7257 0.7499 0.069 Uiso 0.5 1 calc PR . . H19D H 0.2135 0.6983 0.7668 0.069 Uiso 0.5 1 calc PR . . H19E H 0.2702 0.7368 0.7622 0.069 Uiso 0.5 1 calc PR . . H19F H 0.2944 0.6934 0.8082 0.069 Uiso 0.5 1 calc PR . . C20 C 0.2469(3) 0.70193(14) 0.4194(3) 0.0362(10) Uani 1 1 d . . . H20A H 0.2308 0.677 0.3856 0.054 Uiso 1 1 calc R . . H20B H 0.2807 0.7185 0.3819 0.054 Uiso 1 1 calc R . . H20C H 0.204 0.7191 0.4352 0.054 Uiso 1 1 calc R . . C21 C 0.4117(2) 0.63300(12) 0.1392(2) 0.0243(8) Uani 1 1 d . . . C22 C 0.3617(3) 0.67033(14) 0.1080(3) 0.0317(10) Uani 1 1 d . . . C23 C 0.4063(3) 0.71114(14) 0.1084(4) 0.0436(12) Uani 1 1 d . . . H23A H 0.374 0.7349 0.0937 0.065 Uiso 1 1 calc R . . H23B H 0.4457 0.7093 0.0633 0.065 Uiso 1 1 calc R . . H23C H 0.4278 0.7154 0.1687 0.065 Uiso 1 1 calc R . . C24 C 0.3283(3) 0.6644(2) 0.0130(3) 0.0559(15) Uani 1 1 d . . . H24A H 0.2999 0.6895 -0.0034 0.084 Uiso 1 1 calc R . . H24B H 0.2958 0.6398 0.0131 0.084 Uiso 1 1 calc R . . H24C H 0.3678 0.6602 -0.0312 0.084 Uiso 1 1 calc R . . C25 C 0.2970(3) 0.67647(14) 0.1736(3) 0.0391(11) Uani 1 1 d . . . H25A H 0.2649 0.6517 0.1714 0.059 Uiso 1 1 calc R . . H25B H 0.269 0.7015 0.156 0.059 Uiso 1 1 calc R . . H25C H 0.3159 0.6801 0.2354 0.059 Uiso 1 1 calc R . . C26 C 0.5077(2) 0.63995(13) 0.0255(3) 0.0293(9) Uani 1 1 d . . . C27 C 0.5654(2) 0.66898(12) 0.0100(3) 0.0306(9) Uani 1 1 d . . . C28 C 0.5870(3) 0.67820(14) -0.0780(3) 0.0336(10) Uani 1 1 d . . . H28 H 0.6249 0.6983 -0.087 0.04 Uiso 1 1 calc R . . C29 C 0.5555(3) 0.65921(17) -0.1537(3) 0.0418(11) Uani 1 1 d . . . C30 C 0.5037(3) 0.62781(16) -0.1373(3) 0.0442(12) Uani 1 1 d . . . H30 H 0.4835 0.6131 -0.1875 0.053 Uiso 1 1 calc R . . C31 C 0.4804(3) 0.61706(15) -0.0504(3) 0.0388(10) Uani 1 1 d . . . C32 C 0.6017(3) 0.69112(15) 0.0868(3) 0.0368(10) Uani 1 1 d . . . H32A H 0.6194 0.6704 0.1309 0.055 Uiso 1 1 calc R . . H32B H 0.5662 0.71 0.1161 0.055 Uiso 1 1 calc R . . H32C H 0.6433 0.7076 0.0639 0.055 Uiso 1 1 calc R . . C33 C 0.5754(4) 0.6735(2) -0.2481(3) 0.0587(15) Uani 1 1 d . . . H33A H 0.6285 0.6701 -0.2575 0.088 Uiso 0.5 1 calc PR . . H33B H 0.5621 0.7032 -0.2556 0.088 Uiso 0.5 1 calc PR . . H33C H 0.5487 0.6565 -0.2927 0.088 Uiso 0.5 1 calc PR . . H33D H 0.531 0.6831 -0.2797 0.088 Uiso 0.5 1 calc PR . . H33E H 0.5975 0.65 -0.2816 0.088 Uiso 0.5 1 calc PR . . H33F H 0.6108 0.6968 -0.2445 0.088 Uiso 0.5 1 calc PR . . C34 C 0.4310(3) 0.57987(17) -0.0364(4) 0.0514(14) Uani 1 1 d . . . H34A H 0.4434 0.5661 0.021 0.077 Uiso 1 1 calc R . . H34B H 0.4375 0.5599 -0.0864 0.077 Uiso 1 1 calc R . . H34C H 0.3797 0.5893 -0.0346 0.077 Uiso 1 1 calc R . . C35 C 0.6769(3) 0.59859(14) 0.3281(3) 0.0358(10) Uani 1 1 d . . . H35A H 0.6421 0.5899 0.3763 0.043 Uiso 1 1 calc R . . H35B H 0.7016 0.6249 0.3472 0.043 Uiso 1 1 calc R . . C36 C 0.7324(4) 0.56465(18) 0.3110(5) 0.0675(18) Uani 1 1 d . . . H36A H 0.7786 0.5702 0.3445 0.081 Uiso 1 1 calc R . . H36B H 0.713 0.5367 0.329 0.081 Uiso 1 1 calc R . . C37 C 0.7445(5) 0.5668(3) 0.2119(6) 0.107(3) Uani 1 1 d . . . H37A H 0.7857 0.5861 0.1977 0.128 Uiso 1 1 calc R . . H37B H 0.7564 0.5385 0.1875 0.128 Uiso 1 1 calc R . . C38 C 0.6756(4) 0.5825(3) 0.1727(4) 0.076(2) Uani 1 1 d . . . H38A H 0.686 0.6015 0.121 0.091 Uiso 1 1 calc R . . H38B H 0.6451 0.5587 0.1508 0.091 Uiso 1 1 calc R . . C39 C 0.2157(5) 0.5821(3) 0.4269(5) 0.085(2) Uani 1 1 d . . . H39A H 0.2574 0.5664 0.4538 0.102 Uiso 1 1 calc R . . H39B H 0.2054 0.6069 0.4655 0.102 Uiso 1 1 calc R . . C40 C 0.1538(7) 0.5564(4) 0.4218(6) 0.145(5) Uani 1 1 d . . . H40A H 0.115 0.5676 0.4621 0.174 Uiso 1 1 calc R . . H40B H 0.1666 0.5277 0.4427 0.174 Uiso 1 1 calc R . . C41 C 0.1260(3) 0.5544(2) 0.3286(5) 0.0649(17) Uani 1 1 d . . . H41A H 0.0792 0.5701 0.3226 0.078 Uiso 1 1 calc R . . H41B H 0.1179 0.5249 0.3096 0.078 Uiso 1 1 calc R . . C42 C 0.1855(3) 0.57452(17) 0.2730(4) 0.0464(12) Uani 1 1 d . . . H42A H 0.2128 0.553 0.238 0.056 Uiso 1 1 calc R . . H42B H 0.1643 0.5952 0.2301 0.056 Uiso 1 1 calc R . . Li1 Li 0.5422(4) 0.6284(2) 0.2308(5) 0.0294(15) Uani 1 1 d . . . Li2 Li 0.3225(4) 0.6253(2) 0.3071(4) 0.0290(15) Uani 1 1 d . . . C1A C 0.5607(12) 0.5 0 0.177(4) Uiso 1 2 d SD . . C2A C 0.5987(12) 0.5361(6) -0.034(2) 0.177(4) Uiso 0.5 1 d PD . . C3A C 0.6696(10) 0.5358(4) -0.0343(12) 0.177(4) Uiso 1 1 d D . . C4A C 0.7447(12) 0.5363(6) -0.038(2) 0.177(4) Uiso 0.5 1 d PD . . C5A C 0.7841(12) 0.5 0 0.177(4) Uiso 1 2 d SD . . C6A C 0.6349(12) 0.5 0 0.177(4) Uiso 0.5 2 d SPD . . C7A C 0.7111(12) 0.5 0 0.177(4) Uiso 0.5 2 d SPD . . 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 0.0352(18) 0.0537(19) 0.0324(16) -0.0025(14) 0.0020(14) 0.0148(15) O2 0.040(2) 0.064(2) 0.0333(17) -0.0053(15) 0.0064(15) -0.0241(17) N1 0.0242(17) 0.0210(14) 0.0222(15) -0.0024(11) -0.0005(14) 0.0004(13) N2 0.0216(17) 0.0275(15) 0.0230(15) -0.0019(12) -0.0005(14) 0.0026(14) N3 0.0229(17) 0.0273(16) 0.0221(16) -0.0014(12) 0.0006(14) 0.0003(14) N4 0.0236(17) 0.0280(15) 0.0219(15) -0.0026(12) 0.0013(14) -0.0001(14) C1 0.025(2) 0.0231(17) 0.0235(18) -0.0046(13) 0.0010(16) 0.0016(16) C2 0.029(2) 0.0248(18) 0.0210(17) -0.0015(14) 0.0011(17) -0.0012(16) C3 0.034(2) 0.0286(19) 0.032(2) -0.0038(16) -0.0029(19) -0.0006(18) C4 0.037(2) 0.0205(18) 0.049(3) -0.0064(16) -0.004(2) -0.0034(17) C5 0.033(2) 0.0234(17) 0.038(2) 0.0017(16) -0.001(2) 0.0038(18) C6 0.029(2) 0.0242(17) 0.0260(19) -0.0017(14) -0.0032(17) 0.0038(17) C7 0.023(2) 0.0259(18) 0.0209(18) 0.0007(14) -0.0010(16) -0.0016(16) C8 0.030(2) 0.0235(18) 0.0230(18) -0.0020(14) -0.0028(17) -0.0009(16) C9 0.034(2) 0.0244(19) 0.038(2) -0.0044(16) 0.003(2) -0.0040(17) C10 0.036(2) 0.0223(18) 0.036(2) -0.0059(15) 0.005(2) 0.0023(18) C11 0.041(3) 0.038(2) 0.029(2) -0.0009(18) -0.011(2) -0.010(2) C12 0.024(2) 0.0201(17) 0.0273(18) -0.0030(14) 0.0030(16) -0.0040(15) C13 0.028(2) 0.0275(19) 0.029(2) 0.0023(15) 0.0002(18) -0.0012(17) C14 0.035(2) 0.034(2) 0.0211(18) 0.0001(15) 0.0007(18) -0.0062(18) C15 0.034(2) 0.0279(19) 0.031(2) -0.0043(16) 0.0072(19) -0.0127(18) C16 0.027(2) 0.0225(17) 0.041(2) -0.0057(16) 0.0114(19) -0.0024(16) C17 0.029(2) 0.0251(18) 0.0269(19) 0.0003(15) 0.0063(18) -0.0016(17) C18 0.040(3) 0.035(2) 0.030(2) 0.0027(16) -0.001(2) 0.0061(19) C19 0.059(3) 0.050(3) 0.029(2) -0.0098(19) 0.009(2) -0.009(3) C20 0.031(2) 0.038(2) 0.039(2) 0.0040(18) -0.001(2) 0.0096(19) C21 0.025(2) 0.0296(18) 0.0185(17) -0.0045(14) -0.0016(16) 0.0010(16) C22 0.030(2) 0.043(2) 0.0225(19) 0.0056(16) 0.0007(18) 0.0081(19) C23 0.038(3) 0.037(2) 0.055(3) 0.016(2) 0.010(2) 0.013(2) C24 0.046(3) 0.090(4) 0.031(3) 0.002(2) -0.011(2) 0.022(3) C25 0.031(2) 0.039(2) 0.047(3) 0.012(2) 0.012(2) 0.014(2) C26 0.029(2) 0.0326(19) 0.0258(19) 0.0008(15) 0.0040(18) 0.0043(17) C27 0.025(2) 0.031(2) 0.035(2) 0.0025(17) 0.0004(18) 0.0062(17) C28 0.032(2) 0.038(2) 0.031(2) 0.0054(17) 0.0091(19) 0.005(2) C29 0.042(3) 0.058(3) 0.025(2) 0.005(2) 0.010(2) 0.006(2) C30 0.050(3) 0.053(3) 0.030(2) -0.0090(19) 0.002(2) 0.001(2) C31 0.037(3) 0.050(2) 0.029(2) -0.0089(18) 0.004(2) 0.000(2) C32 0.036(3) 0.044(2) 0.031(2) 0.0066(18) 0.001(2) -0.005(2) C33 0.078(4) 0.071(4) 0.027(2) 0.003(2) 0.012(3) 0.004(3) C34 0.053(3) 0.063(3) 0.038(3) -0.019(2) 0.010(3) -0.020(3) C35 0.033(2) 0.040(2) 0.034(2) -0.0003(18) -0.006(2) -0.005(2) C36 0.077(5) 0.049(3) 0.076(4) -0.012(3) -0.026(4) 0.021(3) C37 0.095(6) 0.142(7) 0.082(5) -0.024(5) -0.007(5) 0.084(6) C38 0.077(5) 0.104(5) 0.046(3) -0.011(3) 0.002(3) 0.052(4) C39 0.081(5) 0.122(6) 0.052(4) 0.013(4) 0.010(4) -0.055(5) C40 0.160(10) 0.210(12) 0.065(5) -0.004(6) 0.033(6) -0.130(10) C41 0.048(3) 0.057(3) 0.090(5) -0.008(3) 0.012(3) -0.020(3) C42 0.030(2) 0.054(3) 0.056(3) -0.014(2) -0.001(2) -0.007(2) Li1 0.027(4) 0.033(3) 0.028(4) -0.001(3) 0.006(3) 0.000(3) Li2 0.029(4) 0.034(3) 0.024(3) 0.000(3) 0.003(3) -0.004(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C38 1.422(7) . ? O1 C35 1.453(5) . ? O1 Li1 1.913(8) . ? O2 C39 1.428(7) . ? O2 C42 1.449(6) . ? O2 Li2 1.923(8) . ? N1 C7 1.325(5) . ? N1 C1 1.468(5) . ? N1 Li1 2.006(8) . ? N2 C21 1.309(5) . ? N2 C2 1.462(5) . ? N2 Li2 1.999(8) . ? N3 C7 1.354(5) . ? N3 C12 1.410(5) . ? N3 Li2 1.995(8) . ? N4 C21 1.369(5) . ? N4 C26 1.408(5) . ? N4 Li1 2.020(8) . ? C1 C6 1.529(5) . ? C1 C2 1.546(5) . ? C2 C3 1.525(5) . ? C3 C4 1.543(6) . ? C4 C5 1.522(6) . ? C5 C6 1.534(6) . ? C7 C8 1.569(5) . ? C8 C9 1.521(6) . ? C8 C11 1.542(6) . ? C8 C10 1.547(6) . ? C12 C13 1.410(6) . ? C12 C17 1.420(6) . ? C13 C14 1.399(6) . ? C13 C18 1.506(6) . ? C14 C15 1.397(6) . ? C15 C16 1.394(7) . ? C15 C19 1.501(6) . ? C16 C17 1.385(6) . ? C17 C20 1.497(6) . ? C21 C22 1.563(6) . ? C22 C23 1.529(7) . ? C22 C25 1.534(6) . ? C22 C24 1.538(6) . ? C26 C27 1.414(6) . ? C26 C31 1.423(6) . ? C27 C28 1.387(6) . ? C27 C32 1.487(6) . ? C28 C29 1.391(7) . ? C29 C30 1.392(8) . ? C29 C33 1.510(6) . ? C30 C31 1.392(7) . ? C31 C34 1.498(7) . ? C35 C36 1.497(8) . ? C36 C37 1.479(11) . ? C37 C38 1.466(10) . ? C39 C40 1.392(11) . ? C40 C41 1.466(12) . ? C41 C42 1.499(8) . ? C1A C6A 1.349(18) . ? C1A C2A 1.431(16) . ? C2A C3A 1.288(16) . ? C3A C4A 1.365(17) . ? C3A C6A 1.395(13) . ? C3A C7A 1.455(14) . ? C4A C5A 1.471(16) . ? C5A C7A 1.327(18) . ? 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 C38 O1 C35 109.6(4) . . ? C38 O1 Li1 124.3(4) . . ? C35 O1 Li1 124.9(3) . . ? C39 O2 C42 109.4(4) . . ? C39 O2 Li2 123.4(4) . . ? C42 O2 Li2 125.7(4) . . ? C7 N1 C1 116.7(3) . . ? C7 N1 Li1 128.8(3) . . ? C1 N1 Li1 104.5(3) . . ? C21 N2 C2 118.8(3) . . ? C21 N2 Li2 126.5(3) . . ? C2 N2 Li2 103.9(3) . . ? C7 N3 C12 122.6(3) . . ? C7 N3 Li2 105.5(3) . . ? C12 N3 Li2 131.2(3) . . ? C21 N4 C26 122.2(3) . . ? C21 N4 Li1 106.0(3) . . ? C26 N4 Li1 129.7(4) . . ? N1 C1 C6 111.5(3) . . ? N1 C1 C2 110.3(3) . . ? C6 C1 C2 109.9(3) . . ? N2 C2 C3 112.0(3) . . ? N2 C2 C1 108.9(3) . . ? C3 C2 C1 109.8(3) . . ? C2 C3 C4 111.2(4) . . ? C5 C4 C3 111.5(3) . . ? C4 C5 C6 110.5(3) . . ? C1 C6 C5 110.1(3) . . ? N1 C7 N3 123.3(3) . . ? N1 C7 C8 114.2(3) . . ? N3 C7 C8 122.1(3) . . ? C9 C8 C11 107.3(4) . . ? C9 C8 C10 107.4(3) . . ? C11 C8 C10 109.6(3) . . ? C9 C8 C7 110.9(3) . . ? C11 C8 C7 111.9(3) . . ? C10 C8 C7 109.7(3) . . ? N3 C12 C13 120.3(3) . . ? N3 C12 C17 121.2(4) . . ? C13 C12 C17 118.0(4) . . ? C14 C13 C12 119.9(4) . . ? C14 C13 C18 119.1(4) . . ? C12 C13 C18 120.8(4) . . ? C15 C14 C13 122.2(4) . . ? C16 C15 C14 116.9(4) . . ? C16 C15 C19 122.4(4) . . ? C14 C15 C19 120.7(4) . . ? C17 C16 C15 122.8(4) . . ? C16 C17 C12 119.7(4) . . ? C16 C17 C20 119.8(4) . . ? C12 C17 C20 120.5(4) . . ? N2 C21 N4 122.4(4) . . ? N2 C21 C22 115.5(4) . . ? N4 C21 C22 121.4(3) . . ? C23 C22 C25 107.2(4) . . ? C23 C22 C24 108.5(4) . . ? C25 C22 C24 106.8(4) . . ? C23 C22 C21 109.4(4) . . ? C25 C22 C21 110.8(3) . . ? C24 C22 C21 113.9(4) . . ? N4 C26 C27 120.9(4) . . ? N4 C26 C31 121.1(4) . . ? C27 C26 C31 117.7(4) . . ? C28 C27 C26 119.9(4) . . ? C28 C27 C32 119.1(4) . . ? C26 C27 C32 121.0(4) . . ? C27 C28 C29 122.8(4) . . ? C30 C29 C28 116.7(4) . . ? C30 C29 C33 122.6(5) . . ? C28 C29 C33 120.7(5) . . ? C29 C30 C31 122.8(5) . . ? C30 C31 C26 119.4(4) . . ? C30 C31 C34 120.2(4) . . ? C26 C31 C34 120.2(4) . . ? O1 C35 C36 105.9(4) . . ? C37 C36 C35 103.6(5) . . ? C38 C37 C36 106.1(6) . . ? O1 C38 C37 106.7(5) . . ? C40 C39 O2 107.9(6) . . ? C39 C40 C41 110.8(7) . . ? C40 C41 C42 104.2(5) . . ? O2 C42 C41 105.9(5) . . ? O1 Li1 N1 112.2(4) . . ? O1 Li1 N4 124.8(4) . . ? N1 Li1 N4 115.6(4) . . ? O2 Li2 N3 112.8(3) . . ? O2 Li2 N2 120.3(4) . . ? N3 Li2 N2 117.9(4) . . ? C2A C1A C2A 122.2(16) 3_565 . ? C3A C2A C1A 118.5(13) . . ? C4A C3A C6A 118.5(13) . . ? C2A C3A C7A 121.6(13) . . ? C3A C4A C5A 117.4(14) . . ? C4A C5A C4A 121.7(18) . 3_565 ? C1A C6A C3A 116.9(8) . . ? C3A C6A C3A 126.2(16) . 3_565 ? C5A C7A C3A 121.2(7) . . ? C3A C7A C3A 117.6(15) 3_565 . ? #===END data_(14)-mar705 _database_code_depnum_ccdc_archive 'CCDC 284727' _audit_creation_date 2005-03-08T14:04:12-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C40 H62 Li2 N4 O2, C7 H8' _chemical_formula_sum 'C47 H70 Li2 N4 O2' _chemical_formula_weight 736.95 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 16.0481(7) _cell_length_b 15.7871(6) _cell_length_c 18.7167(7) _cell_angle_alpha 90 _cell_angle_beta 104.274(2) _cell_angle_gamma 90 _cell_volume 4595.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 80909 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.065 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.154504E-1 _diffrn_orient_matrix_ub_12 -0.308193E-1 _diffrn_orient_matrix_ub_13 0.416111E-1 _diffrn_orient_matrix_ub_21 0.451881E-1 _diffrn_orient_matrix_ub_22 -0.433321E-1 _diffrn_orient_matrix_ub_23 -0.8762E-3 _diffrn_orient_matrix_ub_31 0.430526E-1 _diffrn_orient_matrix_ub_32 0.344212E-1 _diffrn_orient_matrix_ub_33 0.361538E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0899 _diffrn_reflns_av_unetI/netI 0.0758 _diffrn_reflns_number 36786 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 26.11 _diffrn_reflns_theta_full 26.11 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _reflns_number_total 8984 _reflns_number_gt 5235 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Both thf ligands were disordered and were included with isotropic C atoms and SADI restraints. 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^)+(0.1158P)^2^+6.2886P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8984 _refine_ls_number_parameters 482 _refine_ls_number_restraints 81 _refine_ls_R_factor_all 0.1653 _refine_ls_R_factor_gt 0.1015 _refine_ls_wR_factor_ref 0.2859 _refine_ls_wR_factor_gt 0.2397 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.497 _refine_diff_density_min -0.463 _refine_diff_density_rms 0.049 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Li1 Li 0.2262(4) 0.0831(4) 0.4726(4) 0.0510(15) Uani 1 1 d . A . Li2 Li 0.2415(5) 0.0618(4) 0.2480(4) 0.0548(17) Uani 1 1 d . A . O1 O 0.17495(19) 0.10808(19) 0.55322(15) 0.0606(8) Uani 1 1 d D . . O2 O 0.2036(2) 0.0670(3) 0.14386(17) 0.0881(12) Uani 1 1 d D . . N1 N 0.24908(19) 0.15715(18) 0.39477(16) 0.0408(7) Uani 1 1 d . . . N2 N 0.17215(19) 0.01034(18) 0.31114(16) 0.0422(7) Uani 1 1 d . . . N3 N 0.3227(2) 0.14584(19) 0.30128(16) 0.0453(8) Uani 1 1 d . . . N4 N 0.2037(2) -0.03295(19) 0.43462(16) 0.0434(7) Uani 1 1 d . . . C1 C 0.1683(2) 0.1639(2) 0.3384(2) 0.0439(9) Uani 1 1 d . A . H1 H 0.1814 0.1795 0.2906 0.053 Uiso 1 1 calc R . . C2 C 0.1191(2) 0.0787(2) 0.3286(2) 0.0442(9) Uani 1 1 d . A . H2 H 0.1039 0.0646 0.3759 0.053 Uiso 1 1 calc R . . C3 C 0.0363(3) 0.0881(3) 0.2685(2) 0.0559(11) Uani 1 1 d . . . H3A H 0.005 0.0335 0.2618 0.067 Uiso 1 1 calc R B . H3B H 0.0502 0.1028 0.2214 0.067 Uiso 1 1 calc R . . C4 C -0.0210(3) 0.1572(3) 0.2887(3) 0.0692(13) Uani 1 1 d . B . H4A H -0.0738 0.1634 0.2484 0.083 Uiso 1 1 calc R . . H4B H -0.0383 0.1407 0.334 0.083 Uiso 1 1 calc R . . C5 C 0.0267(3) 0.2416(3) 0.3012(3) 0.0709(13) Uani 1 1 d . . . H5A H -0.0096 0.2844 0.3177 0.085 Uiso 1 1 calc R B . H5B H 0.0378 0.2614 0.2542 0.085 Uiso 1 1 calc R . . C6 C 0.1119(3) 0.2331(3) 0.3591(2) 0.0564(11) Uani 1 1 d . A . H6A H 0.1004 0.2194 0.4074 0.068 Uiso 1 1 calc R . . H6B H 0.1429 0.2878 0.364 0.068 Uiso 1 1 calc R . . C7 C 0.3204(2) 0.1560(2) 0.3731(2) 0.0420(9) Uani 1 1 d . A . C8 C 0.4044(2) 0.1569(2) 0.4358(2) 0.0485(9) Uani 1 1 d . . . C9 C 0.4775(3) 0.1100(4) 0.4142(3) 0.0852(17) Uani 1 1 d . A . H9A H 0.4591 0.0521 0.399 0.128 Uiso 1 1 calc R . . H9B H 0.5276 0.108 0.4565 0.128 Uiso 1 1 calc R . . H9C H 0.4927 0.1396 0.3732 0.128 Uiso 1 1 calc R . . C10 C 0.4309(4) 0.2479(3) 0.4589(3) 0.0851(17) Uani 1 1 d . A . H10A H 0.3833 0.2769 0.4727 0.128 Uiso 1 1 calc R . . H10B H 0.4453 0.2778 0.4176 0.128 Uiso 1 1 calc R . . H10C H 0.4812 0.2471 0.501 0.128 Uiso 1 1 calc R . . C11 C 0.3893(3) 0.1128(3) 0.5044(2) 0.0612(11) Uani 1 1 d . A . H11A H 0.3426 0.1414 0.5202 0.092 Uiso 1 1 calc R . . H11B H 0.442 0.1153 0.5442 0.092 Uiso 1 1 calc R . . H11C H 0.3736 0.0535 0.4928 0.092 Uiso 1 1 calc R . . C12 C 0.3810(2) 0.1867(2) 0.26886(19) 0.0407(8) Uani 1 1 d . A . C13 C 0.3914(2) 0.2750(2) 0.2718(2) 0.0457(9) Uani 1 1 d . . . H13 H 0.362 0.3074 0.3007 0.055 Uiso 1 1 calc R A . C14 C 0.4435(3) 0.3163(2) 0.2335(2) 0.0484(9) Uani 1 1 d . A . C15 C 0.4846(3) 0.2691(2) 0.1903(2) 0.0501(10) Uani 1 1 d . . . H15 H 0.5195 0.2969 0.1633 0.06 Uiso 1 1 calc R A . C16 C 0.4755(2) 0.1814(2) 0.1856(2) 0.0459(9) Uani 1 1 d . A . C17 C 0.4235(3) 0.1415(2) 0.2243(2) 0.0474(9) Uani 1 1 d . . . H17 H 0.4164 0.0818 0.2205 0.057 Uiso 1 1 calc R A . C18 C 0.4536(3) 0.4112(3) 0.2381(3) 0.0713(13) Uani 1 1 d . . . H18A H 0.4204 0.434 0.2712 0.107 Uiso 0.5 1 calc PR A . H18B H 0.4324 0.4358 0.1889 0.107 Uiso 0.5 1 calc PR . . H18C H 0.5144 0.4256 0.2571 0.107 Uiso 0.5 1 calc PR . . H18D H 0.4911 0.4296 0.2069 0.107 Uiso 0.5 1 calc PR . . H18E H 0.4791 0.4278 0.2893 0.107 Uiso 0.5 1 calc PR . . H18F H 0.3971 0.4381 0.221 0.107 Uiso 0.5 1 calc PR . . C19 C 0.5223(3) 0.1305(3) 0.1395(2) 0.0626(12) Uani 1 1 d . . . H19A H 0.5559 0.1687 0.1161 0.094 Uiso 0.5 1 calc PR A . H19B H 0.4805 0.0997 0.1013 0.094 Uiso 0.5 1 calc PR . . H19C H 0.561 0.0901 0.171 0.094 Uiso 0.5 1 calc PR . . H19D H 0.509 0.0703 0.1428 0.094 Uiso 0.5 1 calc PR . . H19E H 0.5844 0.1393 0.1577 0.094 Uiso 0.5 1 calc PR . . H19F H 0.5039 0.149 0.088 0.094 Uiso 0.5 1 calc PR . . C20 C 0.2049(2) -0.0449(2) 0.3635(2) 0.0410(8) Uani 1 1 d . A . C21 C 0.2522(2) -0.1205(2) 0.3382(2) 0.0451(9) Uani 1 1 d . . . C22 C 0.2936(3) -0.0934(3) 0.2764(2) 0.0588(11) Uani 1 1 d . A . H22A H 0.2495 -0.0701 0.2353 0.088 Uiso 1 1 calc R . . H22B H 0.3204 -0.1427 0.2593 0.088 Uiso 1 1 calc R . . H22C H 0.3375 -0.0503 0.2949 0.088 Uiso 1 1 calc R . . C23 C 0.3239(3) -0.1561(3) 0.3999(2) 0.0614(11) Uani 1 1 d . A . H23A H 0.3514 -0.2037 0.381 0.092 Uiso 1 1 calc R . . H23B H 0.2999 -0.1757 0.4403 0.092 Uiso 1 1 calc R . . H23C H 0.3667 -0.1118 0.418 0.092 Uiso 1 1 calc R . . C24 C 0.1871(3) -0.1908(3) 0.3075(3) 0.0660(12) Uani 1 1 d . A . H24A H 0.1409 -0.1678 0.2679 0.099 Uiso 1 1 calc R . . H24B H 0.1628 -0.2127 0.347 0.099 Uiso 1 1 calc R . . H24C H 0.2161 -0.2368 0.288 0.099 Uiso 1 1 calc R . . C25 C 0.1994(2) -0.0968(2) 0.4852(2) 0.0430(9) Uani 1 1 d . A . C26 C 0.2554(3) -0.0942(2) 0.5558(2) 0.0501(10) Uani 1 1 d . . . H26 H 0.2995 -0.0526 0.5662 0.06 Uiso 1 1 calc R A . C27 C 0.2485(3) -0.1506(3) 0.6105(2) 0.0552(10) Uani 1 1 d . A . C28 C 0.1841(3) -0.2113(3) 0.5953(3) 0.0603(11) Uani 1 1 d . . . H28 H 0.179 -0.2502 0.6328 0.072 Uiso 1 1 calc R A . C29 C 0.1270(3) -0.2162(3) 0.5265(3) 0.0549(10) Uani 1 1 d . A . C30 C 0.1346(2) -0.1583(2) 0.4728(2) 0.0493(9) Uani 1 1 d . . . H30 H 0.0946 -0.1605 0.426 0.059 Uiso 1 1 calc R A . C31 C 0.3113(4) -0.1464(3) 0.6851(3) 0.0805(15) Uani 1 1 d . . . H31A H 0.3524 -0.1004 0.6854 0.121 Uiso 0.5 1 calc PR A . H31B H 0.3422 -0.2002 0.6953 0.121 Uiso 0.5 1 calc PR . . H31C H 0.28 -0.1357 0.723 0.121 Uiso 0.5 1 calc PR . . H31D H 0.2973 -0.1905 0.7171 0.121 Uiso 0.5 1 calc PR . . H31E H 0.3075 -0.0907 0.7072 0.121 Uiso 0.5 1 calc PR . . H31F H 0.3698 -0.1552 0.6795 0.121 Uiso 0.5 1 calc PR . . C32 C 0.0569(3) -0.2820(3) 0.5095(3) 0.0785(15) Uani 1 1 d . . . H32A H 0.024 -0.2758 0.4582 0.118 Uiso 0.5 1 calc PR A . H32B H 0.0186 -0.2743 0.5424 0.118 Uiso 0.5 1 calc PR . . H32C H 0.0826 -0.3386 0.5167 0.118 Uiso 0.5 1 calc PR . . H32D H 0.0594 -0.3167 0.5533 0.118 Uiso 0.5 1 calc PR . . H32E H 0.0648 -0.3182 0.4691 0.118 Uiso 0.5 1 calc PR . . H32F H 0.0008 -0.2538 0.4948 0.118 Uiso 0.5 1 calc PR . . C33 C 0.2201(7) 0.1069(11) 0.6318(5) 0.063(4) Uiso 0.408(18) 1 d PD A 1 H33A H 0.2416 0.164 0.649 0.076 Uiso 0.408(18) 1 calc PR A 1 H33B H 0.2691 0.0669 0.6411 0.076 Uiso 0.408(18) 1 calc PR A 1 C34 C 0.1536(9) 0.0785(14) 0.6688(9) 0.102(6) Uiso 0.408(18) 1 d PD A 1 H34A H 0.1329 0.1281 0.692 0.122 Uiso 0.408(18) 1 calc PR A 1 H34B H 0.1799 0.0383 0.7086 0.122 Uiso 0.408(18) 1 calc PR A 1 C35 C 0.0789(10) 0.0369(13) 0.6183(8) 0.103(6) Uiso 0.408(18) 1 d PD A 1 H35A H 0.0835 -0.0256 0.6194 0.124 Uiso 0.408(18) 1 calc PR A 1 H35B H 0.0233 0.0547 0.6275 0.124 Uiso 0.408(18) 1 calc PR A 1 C36 C 0.0930(3) 0.0720(3) 0.5530(3) 0.0783(14) Uiso 0.408(18) 1 d PD A 1 H36A H 0.0491 0.1167 0.5364 0.094 Uiso 0.408(18) 1 calc PR A 1 H36B H 0.0812 0.0271 0.515 0.094 Uiso 0.408(18) 1 calc PR A 1 C37 C 0.1492(5) 0.0101(5) 0.0958(4) 0.120(2) Uiso 0.522(14) 1 d PD B 1 H37A H 0.1855 -0.0358 0.0839 0.144 Uiso 0.522(14) 1 calc PR B 1 H37B H 0.1104 -0.016 0.1233 0.144 Uiso 0.522(14) 1 calc PR B 1 C38 C 0.0980(9) 0.0414(9) 0.0291(7) 0.105(5) Uiso 0.522(14) 1 d PD B 1 H38A H 0.0449 0.0698 0.0345 0.126 Uiso 0.522(14) 1 calc PR B 1 H38B H 0.0846 -0.0016 -0.0106 0.126 Uiso 0.522(14) 1 calc PR B 1 C39 C 0.1677(7) 0.1021(11) 0.0219(6) 0.087(4) Uiso 0.522(14) 1 d PD B 1 H39A H 0.1417 0.1586 0.0087 0.104 Uiso 0.522(14) 1 calc PR B 1 H39B H 0.1919 0.083 -0.0192 0.104 Uiso 0.522(14) 1 calc PR B 1 C40 C 0.2418(6) 0.1108(7) 0.0922(5) 0.075(4) Uiso 0.522(14) 1 d PD B 1 H40A H 0.295 0.0826 0.0866 0.09 Uiso 0.522(14) 1 calc PR B 1 H40B H 0.2543 0.1709 0.1062 0.09 Uiso 0.522(14) 1 calc PR B 1 C33A C 0.2182(7) 0.1453(10) 0.6211(6) 0.098(4) Uiso 0.592(18) 1 d PD A 2 H33C H 0.23 0.2058 0.6139 0.117 Uiso 0.592(18) 1 calc PR A 2 H33D H 0.2736 0.1161 0.6414 0.117 Uiso 0.592(18) 1 calc PR A 2 C34A C 0.1623(7) 0.1367(10) 0.6715(7) 0.114(5) Uiso 0.592(18) 1 d PD A 2 H34C H 0.1949 0.1145 0.7197 0.137 Uiso 0.592(18) 1 calc PR A 2 H34D H 0.1374 0.1923 0.6794 0.137 Uiso 0.592(18) 1 calc PR A 2 C35A C 0.0963(8) 0.0790(8) 0.6372(5) 0.093(4) Uiso 0.592(18) 1 d PD A 2 H35C H 0.0401 0.0991 0.6437 0.111 Uiso 0.592(18) 1 calc PR A 2 H35D H 0.1079 0.0226 0.6607 0.111 Uiso 0.592(18) 1 calc PR A 2 C36A C 0.0930(3) 0.0720(3) 0.5530(3) 0.0783(14) Uiso 0.592(18) 1 d P A 2 H36C H 0.0884 0.0125 0.5359 0.094 Uiso 0.592(18) 1 calc PR A 2 H36D H 0.045 0.1054 0.5224 0.094 Uiso 0.592(18) 1 calc PR A 2 C37A C 0.1492(5) 0.0101(5) 0.0958(4) 0.120(2) Uiso 0.478(14) 1 d P B 2 H37C H 0.0942 0.0011 0.1098 0.144 Uiso 0.478(14) 1 calc PR B 2 H37D H 0.1774 -0.0451 0.0929 0.144 Uiso 0.478(14) 1 calc PR B 2 C38A C 0.1366(12) 0.0633(9) 0.0211(6) 0.091(4) Uiso 0.478(14) 1 d PD B 2 H38C H 0.1519 0.0277 -0.0172 0.109 Uiso 0.478(14) 1 calc PR B 2 H38D H 0.0755 0.0799 0.0034 0.109 Uiso 0.478(14) 1 calc PR B 2 C39A C 0.1926(11) 0.1424(11) 0.0336(8) 0.116(6) Uiso 0.478(14) 1 d PD B 2 H39C H 0.248 0.133 0.0205 0.14 Uiso 0.478(14) 1 calc PR B 2 H39D H 0.1628 0.1916 0.0059 0.14 Uiso 0.478(14) 1 calc PR B 2 C40A C 0.2043(12) 0.1524(9) 0.1133(8) 0.123(6) Uiso 0.478(14) 1 d PD B 2 H40C H 0.1572 0.1869 0.1238 0.147 Uiso 0.478(14) 1 calc PR B 2 H40D H 0.2597 0.1809 0.1353 0.147 Uiso 0.478(14) 1 calc PR B 2 C1S C 0.3301(6) 0.5851(6) 0.4979(5) 0.127(3) Uani 1 1 d . C 2 C2S C 0.2594(5) 0.6171(4) 0.4550(5) 0.101(2) Uani 1 1 d . C 2 H2S H 0.2349 0.6673 0.4691 0.121 Uiso 1 1 calc R C 2 C3S C 0.2219(9) 0.5781(10) 0.3905(7) 0.196(6) Uani 1 1 d . C 2 H3S H 0.1725 0.6037 0.3595 0.235 Uiso 1 1 calc R C 2 C4S C 0.2508(19) 0.5043(14) 0.3675(8) 0.287(16) Uani 1 1 d . C 2 H4S H 0.2224 0.4709 0.3264 0.344 Uiso 1 1 calc R C 2 C5S C 0.333(2) 0.4864(12) 0.4180(19) 0.32(2) Uani 1 1 d . C 2 H5S H 0.3699 0.4498 0.3991 0.389 Uiso 1 1 calc R C 2 C6S C 0.3606(13) 0.5088(12) 0.4750(12) 0.287(16) Uani 1 1 d . C 2 H6S H 0.4038 0.477 0.5079 0.344 Uiso 1 1 calc R C 2 C7S C 0.3722(8) 0.6225(11) 0.5653(7) 0.254(9) Uani 1 1 d . C 2 H7S1 H 0.3409 0.6735 0.5735 0.381 Uiso 0.5 1 calc PR C 2 H7S2 H 0.4309 0.638 0.5639 0.381 Uiso 0.5 1 calc PR C 2 H7S3 H 0.3742 0.5822 0.6055 0.381 Uiso 0.5 1 calc PR C 2 H7S4 H 0.4231 0.589 0.5885 0.381 Uiso 0.5 1 calc PR C 2 H7S5 H 0.3331 0.6245 0.598 0.381 Uiso 0.5 1 calc PR C 2 H7S6 H 0.3898 0.6802 0.5565 0.381 Uiso 0.5 1 calc PR C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Li1 0.057(4) 0.050(4) 0.048(4) -0.002(3) 0.017(3) -0.004(3) Li2 0.068(4) 0.054(4) 0.044(4) -0.010(3) 0.016(3) -0.017(3) O1 0.0635(18) 0.0689(19) 0.0537(17) -0.0065(14) 0.0229(14) -0.0059(15) O2 0.105(3) 0.106(3) 0.0474(18) -0.0043(18) 0.0074(18) -0.042(2) N1 0.0421(17) 0.0397(16) 0.0406(16) -0.0019(13) 0.0101(14) -0.0004(13) N2 0.0411(16) 0.0435(17) 0.0411(16) -0.0022(14) 0.0086(13) -0.0006(14) N3 0.0499(18) 0.0472(18) 0.0399(17) -0.0008(14) 0.0134(14) -0.0081(14) N4 0.0509(18) 0.0414(17) 0.0396(16) -0.0003(13) 0.0146(14) -0.0001(14) C1 0.047(2) 0.044(2) 0.043(2) 0.0040(16) 0.0162(17) 0.0015(17) C2 0.043(2) 0.046(2) 0.043(2) 0.0014(16) 0.0088(16) 0.0006(17) C3 0.046(2) 0.058(2) 0.059(3) 0.005(2) 0.0031(19) -0.0017(19) C4 0.047(2) 0.074(3) 0.080(3) 0.004(3) 0.004(2) 0.010(2) C5 0.061(3) 0.059(3) 0.087(3) 0.010(2) 0.008(2) 0.019(2) C6 0.056(2) 0.046(2) 0.067(3) 0.0009(19) 0.014(2) 0.0083(19) C7 0.052(2) 0.0320(18) 0.043(2) -0.0004(15) 0.0143(17) -0.0046(16) C8 0.050(2) 0.054(2) 0.039(2) -0.0027(17) 0.0069(17) -0.0102(18) C9 0.051(3) 0.143(5) 0.057(3) 0.004(3) 0.005(2) 0.022(3) C10 0.100(4) 0.073(3) 0.065(3) 0.000(3) -0.011(3) -0.037(3) C11 0.054(2) 0.076(3) 0.048(2) 0.008(2) 0.0028(19) -0.009(2) C12 0.0409(19) 0.043(2) 0.0369(18) -0.0003(16) 0.0074(15) -0.0044(16) C13 0.048(2) 0.047(2) 0.044(2) -0.0022(17) 0.0134(17) 0.0012(17) C14 0.051(2) 0.042(2) 0.052(2) 0.0033(17) 0.0121(19) -0.0035(18) C15 0.052(2) 0.053(2) 0.049(2) 0.0099(18) 0.0187(18) -0.0048(19) C16 0.048(2) 0.049(2) 0.040(2) 0.0050(17) 0.0116(17) 0.0019(18) C17 0.060(2) 0.0383(19) 0.045(2) 0.0016(16) 0.0148(18) -0.0048(18) C18 0.088(3) 0.043(2) 0.089(3) 0.000(2) 0.034(3) -0.009(2) C19 0.082(3) 0.055(3) 0.058(3) 0.004(2) 0.033(2) 0.002(2) C20 0.0386(19) 0.0397(19) 0.044(2) -0.0045(16) 0.0085(16) -0.0073(16) C21 0.047(2) 0.044(2) 0.046(2) -0.0051(17) 0.0146(17) -0.0014(17) C22 0.067(3) 0.058(3) 0.058(3) -0.003(2) 0.026(2) 0.006(2) C23 0.060(3) 0.066(3) 0.062(3) 0.000(2) 0.021(2) 0.019(2) C24 0.070(3) 0.055(3) 0.079(3) -0.024(2) 0.029(2) -0.010(2) C25 0.048(2) 0.0374(19) 0.048(2) 0.0015(16) 0.0199(17) 0.0058(16) C26 0.059(2) 0.044(2) 0.048(2) 0.0052(17) 0.0172(19) -0.0001(18) C27 0.068(3) 0.052(2) 0.048(2) 0.0068(19) 0.020(2) 0.000(2) C28 0.075(3) 0.052(2) 0.062(3) 0.016(2) 0.031(2) 0.004(2) C29 0.054(2) 0.048(2) 0.071(3) 0.003(2) 0.031(2) -0.0033(19) C30 0.046(2) 0.046(2) 0.058(2) 0.0007(18) 0.0170(18) 0.0043(18) C31 0.105(4) 0.081(3) 0.052(3) 0.020(2) 0.013(3) -0.008(3) C32 0.076(3) 0.061(3) 0.106(4) 0.008(3) 0.037(3) -0.013(3) C1S 0.106(6) 0.160(7) 0.139(7) 0.055(6) 0.073(6) 0.010(6) C2S 0.105(5) 0.078(4) 0.129(6) 0.039(4) 0.047(5) 0.030(4) C3S 0.249(13) 0.201(12) 0.123(9) 0.079(9) 0.017(9) -0.044(12) C4S 0.54(4) 0.24(2) 0.139(11) -0.096(13) 0.180(18) -0.16(2) C5S 0.52(4) 0.134(11) 0.49(4) 0.11(2) 0.46(4) 0.081(18) C6S 0.34(2) 0.254(18) 0.39(3) 0.25(2) 0.33(2) 0.223(17) C7S 0.169(10) 0.43(2) 0.157(10) 0.005(12) 0.027(8) -0.170(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Li1 O1 1.929(7) . ? Li1 N4 1.966(7) . ? Li1 N1 1.972(7) . ? Li2 O2 1.895(7) . ? Li2 N3 1.953(7) . ? Li2 N2 1.986(7) . ? O1 C33A 1.417(9) . ? O1 C36 1.433(6) . ? O1 C33 1.471(10) . ? O2 C37 1.410(7) . ? O2 C40 1.444(9) . ? O2 C40A 1.467(12) . ? N1 C7 1.305(5) . ? N1 C1 1.459(4) . ? N2 C20 1.320(4) . ? N2 C2 1.461(5) . ? N3 C7 1.363(5) . ? N3 C12 1.393(5) . ? N4 C20 1.349(5) . ? N4 C25 1.396(5) . ? C1 C6 1.527(5) . ? C1 C2 1.548(5) . ? C1 H1 1 . ? C2 C3 1.522(5) . ? C2 H2 1 . ? C3 C4 1.534(6) . ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C5 1.525(7) . ? C4 H4A 0.99 . ? C4 H4B 0.99 . ? C5 C6 1.526(6) . ? C5 H5A 0.99 . ? C5 H5B 0.99 . ? C6 H6A 0.99 . ? C6 H6B 0.99 . ? C7 C8 1.554(5) . ? C8 C9 1.525(6) . ? C8 C10 1.529(6) . ? C8 C11 1.531(6) . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 H11A 0.98 . ? C11 H11B 0.98 . ? C11 H11C 0.98 . ? C12 C17 1.396(5) . ? C12 C13 1.403(5) . ? C13 C14 1.390(5) . ? C13 H13 0.95 . ? C14 C15 1.381(6) . ? C14 C18 1.508(6) . ? C15 C16 1.393(5) . ? C15 H15 0.95 . ? C16 C17 1.385(5) . ? C16 C19 1.507(6) . ? C17 H17 0.95 . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? C18 H18D 0.98 . ? C18 H18E 0.98 . ? C18 H18F 0.98 . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C19 H19D 0.98 . ? C19 H19E 0.98 . ? C19 H19F 0.98 . ? C20 C21 1.550(5) . ? C21 C23 1.522(6) . ? C21 C22 1.531(6) . ? C21 C24 1.535(6) . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 H24A 0.98 . ? C24 H24B 0.98 . ? C24 H24C 0.98 . ? C25 C30 1.400(5) . ? C25 C26 1.403(5) . ? C26 C27 1.382(5) . ? C26 H26 0.95 . ? C27 C28 1.387(6) . ? C27 C31 1.508(6) . ? C28 C29 1.387(6) . ? C28 H28 0.95 . ? C29 C30 1.387(6) . ? C29 C32 1.506(6) . ? C30 H30 0.95 . ? C31 H31A 0.98 . ? C31 H31B 0.98 . ? C31 H31C 0.98 . ? C31 H31D 0.98 . ? C31 H31E 0.98 . ? C31 H31F 0.98 . ? C32 H32A 0.98 . ? C32 H32B 0.98 . ? C32 H32C 0.98 . ? C32 H32D 0.98 . ? C32 H32E 0.98 . ? C32 H32F 0.98 . ? C33 C34 1.478(13) . ? C33 H33A 0.99 . ? C33 H33B 0.99 . ? C34 C35 1.484(14) . ? C34 H34A 0.99 . ? C34 H34B 0.99 . ? C35 C36 1.410(12) . ? C35 H35A 0.99 . ? C35 H35B 0.99 . ? C36 H36A 0.99 . ? C36 H36B 0.99 . ? C37 C38 1.405(11) . ? C37 H37A 0.99 . ? C37 H37B 0.99 . ? C38 C39 1.503(13) . ? C38 H38A 0.99 . ? C38 H38B 0.99 . ? C39 C40 1.547(11) . ? C39 H39A 0.99 . ? C39 H39B 0.99 . ? C40 H40A 0.99 . ? C40 H40B 0.99 . ? C33A C34A 1.460(11) . ? C33A H33C 0.99 . ? C33A H33D 0.99 . ? C34A C35A 1.425(12) . ? C34A H34C 0.99 . ? C34A H34D 0.99 . ? C35A H35C 0.99 . ? C35A H35D 0.99 . ? C38A C39A 1.522(13) . ? C38A H38C 0.99 . ? C38A H38D 0.99 . ? C39A C40A 1.465(13) . ? C39A H39C 0.99 . ? C39A H39D 0.99 . ? C40A H40C 0.99 . ? C40A H40D 0.99 . ? C1S C2S 1.319(10) . ? C1S C6S 1.406(18) . ? C1S C7S 1.407(13) . ? C2S C3S 1.357(15) . ? C2S H2S 0.95 . ? C3S C4S 1.36(2) . ? C3S H3S 0.95 . ? C4S C5S 1.45(4) . ? C4S H4S 0.95 . ? C5S C6S 1.11(4) . ? C5S H5S 0.95 . ? C6S H6S 0.95 . ? C7S H7S1 0.98 . ? C7S H7S2 0.98 . ? C7S H7S3 0.98 . ? C7S H7S4 0.98 . ? C7S H7S5 0.98 . ? C7S H7S6 0.98 . ? 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 Li1 N4 113.4(3) . . ? O1 Li1 N1 130.5(4) . . ? N4 Li1 N1 109.7(3) . . ? O2 Li2 N3 120.0(4) . . ? O2 Li2 N2 123.0(4) . . ? N3 Li2 N2 112.0(3) . . ? C33A O1 C36 114.5(6) . . ? C36 O1 C33 102.9(6) . . ? C33A O1 Li1 125.3(5) . . ? C36 O1 Li1 119.0(3) . . ? C33 O1 Li1 125.4(5) . . ? C37 O2 C40 100.2(5) . . ? C37 O2 C40A 113.6(7) . . ? C37 O2 Li2 128.3(4) . . ? C40 O2 Li2 128.9(5) . . ? C40A O2 Li2 114.1(7) . . ? C7 N1 C1 117.8(3) . . ? C7 N1 Li1 123.9(3) . . ? C1 N1 Li1 106.5(3) . . ? C20 N2 C2 118.0(3) . . ? C20 N2 Li2 122.2(3) . . ? C2 N2 Li2 105.9(3) . . ? C7 N3 C12 124.0(3) . . ? C7 N3 Li2 114.0(3) . . ? C12 N3 Li2 121.8(3) . . ? C20 N4 C25 125.7(3) . . ? C20 N4 Li1 116.1(3) . . ? C25 N4 Li1 117.5(3) . . ? N1 C1 C6 110.3(3) . . ? N1 C1 C2 111.0(3) . . ? C6 C1 C2 109.5(3) . . ? N1 C1 H1 108.7 . . ? C6 C1 H1 108.7 . . ? C2 C1 H1 108.7 . . ? N2 C2 C3 110.9(3) . . ? N2 C2 C1 111.2(3) . . ? C3 C2 C1 109.3(3) . . ? N2 C2 H2 108.5 . . ? C3 C2 H2 108.5 . . ? C1 C2 H2 108.5 . . ? C2 C3 C4 110.8(3) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 110.5(4) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 111.1(4) . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108 . . ? C5 C6 C1 111.5(4) . . ? C5 C6 H6A 109.3 . . ? C1 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C1 C6 H6B 109.3 . . ? H6A C6 H6B 108 . . ? N1 C7 N3 123.2(3) . . ? N1 C7 C8 115.4(3) . . ? N3 C7 C8 121.1(3) . . ? C9 C8 C10 110.6(4) . . ? C9 C8 C11 107.0(4) . . ? C10 C8 C11 106.3(4) . . ? C9 C8 C7 112.0(3) . . ? C10 C8 C7 110.6(3) . . ? C11 C8 C7 110.0(3) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 C17 120.2(3) . . ? N3 C12 C13 121.9(3) . . ? C17 C12 C13 117.4(3) . . ? C14 C13 C12 121.7(4) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C15 C14 C13 118.9(3) . . ? C15 C14 C18 120.6(4) . . ? C13 C14 C18 120.5(4) . . ? C14 C15 C16 121.1(4) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C17 C16 C15 119.0(4) . . ? C17 C16 C19 120.5(4) . . ? C15 C16 C19 120.5(4) . . ? C16 C17 C12 121.8(4) . . ? C16 C17 H17 119.1 . . ? C12 C17 H17 119.1 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C14 C18 H18D 109.5 . . ? H18A C18 H18D 141.1 . . ? H18B C18 H18D 56.3 . . ? H18C C18 H18D 56.3 . . ? C14 C18 H18E 109.5 . . ? H18A C18 H18E 56.3 . . ? H18B C18 H18E 141.1 . . ? H18C C18 H18E 56.3 . . ? H18D C18 H18E 109.5 . . ? C14 C18 H18F 109.5 . . ? H18A C18 H18F 56.3 . . ? H18B C18 H18F 56.3 . . ? H18C C18 H18F 141.1 . . ? H18D C18 H18F 109.5 . . ? H18E C18 H18F 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C16 C19 H19D 109.5 . . ? H19A C19 H19D 141.1 . . ? H19B C19 H19D 56.3 . . ? H19C C19 H19D 56.3 . . ? C16 C19 H19E 109.5 . . ? H19A C19 H19E 56.3 . . ? H19B C19 H19E 141.1 . . ? H19C C19 H19E 56.3 . . ? H19D C19 H19E 109.5 . . ? C16 C19 H19F 109.5 . . ? H19A C19 H19F 56.3 . . ? H19B C19 H19F 56.3 . . ? H19C C19 H19F 141.1 . . ? H19D C19 H19F 109.5 . . ? H19E C19 H19F 109.5 . . ? N2 C20 N4 122.7(3) . . ? N2 C20 C21 114.7(3) . . ? N4 C20 C21 122.4(3) . . ? C23 C21 C22 106.7(3) . . ? C23 C21 C24 109.5(4) . . ? C22 C21 C24 107.5(3) . . ? C23 C21 C20 112.9(3) . . ? C22 C21 C20 110.7(3) . . ? C24 C21 C20 109.4(3) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N4 C25 C30 123.2(3) . . ? N4 C25 C26 119.4(3) . . ? C30 C25 C26 117.0(3) . . ? C27 C26 C25 122.0(4) . . ? C27 C26 H26 119 . . ? C25 C26 H26 119 . . ? C26 C27 C28 119.0(4) . . ? C26 C27 C31 120.0(4) . . ? C28 C27 C31 120.9(4) . . ? C29 C28 C27 121.2(4) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? C28 C29 C30 118.7(4) . . ? C28 C29 C32 121.6(4) . . ? C30 C29 C32 119.7(4) . . ? C29 C30 C25 122.1(4) . . ? C29 C30 H30 118.9 . . ? C25 C30 H30 118.9 . . ? C27 C31 H31A 109.5 . . ? C27 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C27 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C27 C31 H31D 109.5 . . ? H31A C31 H31D 141.1 . . ? H31B C31 H31D 56.3 . . ? H31C C31 H31D 56.3 . . ? C27 C31 H31E 109.5 . . ? H31A C31 H31E 56.3 . . ? H31B C31 H31E 141.1 . . ? H31C C31 H31E 56.3 . . ? H31D C31 H31E 109.5 . . ? C27 C31 H31F 109.5 . . ? H31A C31 H31F 56.3 . . ? H31B C31 H31F 56.3 . . ? H31C C31 H31F 141.1 . . ? H31D C31 H31F 109.5 . . ? H31E C31 H31F 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C29 C32 H32D 109.5 . . ? H32A C32 H32D 141.1 . . ? H32B C32 H32D 56.3 . . ? H32C C32 H32D 56.3 . . ? C29 C32 H32E 109.5 . . ? H32A C32 H32E 56.3 . . ? H32B C32 H32E 141.1 . . ? H32C C32 H32E 56.3 . . ? H32D C32 H32E 109.5 . . ? C29 C32 H32F 109.5 . . ? H32A C32 H32F 56.3 . . ? H32B C32 H32F 56.3 . . ? H32C C32 H32F 141.1 . . ? H32D C32 H32F 109.5 . . ? H32E C32 H32F 109.5 . . ? O1 C33 C34 103.8(9) . . ? O1 C33 H33A 111 . . ? C34 C33 H33A 111 . . ? O1 C33 H33B 111 . . ? C34 C33 H33B 111 . . ? H33A C33 H33B 109 . . ? C33 C34 C35 113.5(12) . . ? C33 C34 H34A 108.9 . . ? C35 C34 H34A 108.9 . . ? C33 C34 H34B 108.9 . . ? C35 C34 H34B 108.9 . . ? H34A C34 H34B 107.7 . . ? C36 C35 C34 95.9(11) . . ? C36 C35 H35A 112.6 . . ? C34 C35 H35A 112.6 . . ? C36 C35 H35B 112.6 . . ? C34 C35 H35B 112.6 . . ? H35A C35 H35B 110.1 . . ? C35 C36 O1 119.8(8) . . ? C35 C36 H36A 107.4 . . ? O1 C36 H36A 107.4 . . ? C35 C36 H36B 107.4 . . ? O1 C36 H36B 107.4 . . ? H36A C36 H36B 106.9 . . ? C38 C37 O2 118.5(8) . . ? C38 C37 H37A 107.7 . . ? O2 C37 H37A 107.7 . . ? C38 C37 H37B 107.7 . . ? O2 C37 H37B 107.7 . . ? H37A C37 H37B 107.1 . . ? C37 C38 C39 91.1(9) . . ? C37 C38 H38A 113.4 . . ? C39 C38 H38A 113.4 . . ? C37 C38 H38B 113.4 . . ? C39 C38 H38B 113.4 . . ? H38A C38 H38B 110.7 . . ? C38 C39 C40 114.4(9) . . ? C38 C39 H39A 108.7 . . ? C40 C39 H39A 108.7 . . ? C38 C39 H39B 108.7 . . ? C40 C39 H39B 108.7 . . ? H39A C39 H39B 107.6 . . ? O2 C40 C39 99.3(8) . . ? O2 C40 H40A 111.9 . . ? C39 C40 H40A 111.9 . . ? O2 C40 H40B 111.9 . . ? C39 C40 H40B 111.9 . . ? H40A C40 H40B 109.6 . . ? O1 C33A C34A 107.3(8) . . ? O1 C33A H33C 110.2 . . ? C34A C33A H33C 110.2 . . ? O1 C33A H33D 110.2 . . ? C34A C33A H33D 110.2 . . ? H33C C33A H33D 108.5 . . ? C35A C34A C33A 106.0(10) . . ? C35A C34A H34C 110.5 . . ? C33A C34A H34C 110.5 . . ? C35A C34A H34D 110.5 . . ? C33A C34A H34D 110.5 . . ? H34C C34A H34D 108.7 . . ? C34A C35A H35C 109.8 . . ? C34A C35A H35D 109.8 . . ? H35C C35A H35D 108.2 . . ? C39A C38A H38C 109.5 . . ? C39A C38A H38D 109.5 . . ? H38C C38A H38D 108.1 . . ? C40A C39A C38A 99.7(11) . . ? C40A C39A H39C 111.8 . . ? C38A C39A H39C 111.8 . . ? C40A C39A H39D 111.8 . . ? C38A C39A H39D 111.8 . . ? H39C C39A H39D 109.6 . . ? C39A C40A O2 106.6(11) . . ? C39A C40A H40C 110.4 . . ? O2 C40A H40C 110.4 . . ? C39A C40A H40D 110.4 . . ? O2 C40A H40D 110.4 . . ? H40C C40A H40D 108.6 . . ? C2S C1S C6S 117.0(13) . . ? C2S C1S C7S 122.5(11) . . ? C6S C1S C7S 120.5(14) . . ? C1S C2S C3S 119.6(10) . . ? C1S C2S H2S 120.2 . . ? C3S C2S H2S 120.2 . . ? C2S C3S C4S 124.0(15) . . ? C2S C3S H3S 118 . . ? C4S C3S H3S 118 . . ? C3S C4S C5S 106.7(15) . . ? C3S C4S H4S 126.7 . . ? C5S C4S H4S 126.7 . . ? C6S C5S C4S 130(2) . . ? C6S C5S H5S 115 . . ? C4S C5S H5S 115 . . ? C5S C6S C1S 119(2) . . ? C5S C6S H6S 120.5 . . ? C1S C6S H6S 120.5 . . ? C1S C7S H7S1 109.5 . . ? C1S C7S H7S2 109.5 . . ? H7S1 C7S H7S2 109.5 . . ? C1S C7S H7S3 109.5 . . ? H7S1 C7S H7S3 109.5 . . ? H7S2 C7S H7S3 109.5 . . ? C1S C7S H7S4 109.5 . . ? H7S1 C7S H7S4 141.1 . . ? H7S2 C7S H7S4 56.3 . . ? H7S3 C7S H7S4 56.3 . . ? C1S C7S H7S5 109.5 . . ? H7S1 C7S H7S5 56.3 . . ? H7S2 C7S H7S5 141.1 . . ? H7S3 C7S H7S5 56.3 . . ? H7S4 C7S H7S5 109.5 . . ? C1S C7S H7S6 109.5 . . ? H7S1 C7S H7S6 56.3 . . ? H7S2 C7S H7S6 56.3 . . ? H7S3 C7S H7S6 141.1 . . ? H7S4 C7S H7S6 109.5 . . ? H7S5 C7S H7S6 109.5 . . ? #===END data_mar1205 _database_code_depnum_ccdc_archive 'CCDC 284728' _audit_creation_date 2005-03-11T10:09:20-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C36 H54 Li2 N4 O2' _chemical_formula_sum 'C36 H54 Li2 N4 O2' _chemical_formula_weight 588.71 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 17.8471(9) _cell_length_b 11.3986(6) _cell_length_c 17.6595(10) _cell_angle_alpha 90 _cell_angle_beta 93.964(3) _cell_angle_gamma 90 _cell_volume 3583.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 20096 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.091 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.357183E-1 _diffrn_orient_matrix_ub_12 -0.636323E-1 _diffrn_orient_matrix_ub_13 -0.174229E-1 _diffrn_orient_matrix_ub_21 0.362342E-1 _diffrn_orient_matrix_ub_22 -0.27387E-1 _diffrn_orient_matrix_ub_23 -0.369596E-1 _diffrn_orient_matrix_ub_31 0.237886E-1 _diffrn_orient_matrix_ub_32 -0.53828E-1 _diffrn_orient_matrix_ub_33 0.394008E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_unetI/netI 0.0474 _diffrn_reflns_number 12759 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.76 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.99 _diffrn_measured_fraction_theta_max 0.99 _reflns_number_total 3480 _reflns_number_gt 2329 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0751P)^2^+2.3488P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3480 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.166 _refine_ls_wR_factor_gt 0.1432 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.19 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.033 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Li Li 0.06208(18) 0.8197(4) 0.35798(18) 0.0519(9) Uani 1 1 d . . . O O 0.12532(8) 0.88229(15) 0.43976(8) 0.0598(5) Uani 1 1 d . . . N1 N 0.08131(8) 0.85210(15) 0.25071(9) 0.0418(4) Uani 1 1 d . . . N2 N 0.04222(8) 0.76914(15) 0.13334(9) 0.0443(4) Uani 1 1 d . . . C1 C 0.03761(10) 0.95756(18) 0.23107(11) 0.0419(5) Uani 1 1 d . . . H1 H 0.0268 0.9594 0.1748 0.05 Uiso 1 1 calc R . . C2 C 0.08196(12) 1.0676(2) 0.25477(12) 0.0548(6) Uani 1 1 d . . . H2A H 0.0938 1.0664 0.3104 0.066 Uiso 1 1 calc R . . H2B H 0.13 1.0681 0.2299 0.066 Uiso 1 1 calc R . . C3 C 0.03800(15) 1.1781(2) 0.23316(13) 0.0670(7) Uani 1 1 d . . . H3A H 0.067 1.2477 0.2516 0.08 Uiso 1 1 calc R . . H3B H 0.0307 1.1835 0.1772 0.08 Uiso 1 1 calc R . . C4 C 0.08628(10) 0.77058(19) 0.19884(11) 0.0435(5) Uani 1 1 d . . . C5 C 0.14103(12) 0.6688(2) 0.22292(12) 0.0581(6) Uani 1 1 d . . . C6 C 0.13535(13) 0.6397(2) 0.30698(13) 0.0624(6) Uani 1 1 d . . . H6A H 0.146 0.7102 0.3376 0.094 Uiso 1 1 calc R . . H6B H 0.1719 0.5784 0.3222 0.094 Uiso 1 1 calc R . . H6C H 0.0846 0.6117 0.3149 0.094 Uiso 1 1 calc R . . C7 C 0.1240(2) 0.5561(3) 0.17880(16) 0.1009(12) Uani 1 1 d . . . H7A H 0.0719 0.5326 0.1848 0.151 Uiso 1 1 calc R . . H7B H 0.158 0.494 0.1983 0.151 Uiso 1 1 calc R . . H7C H 0.131 0.5693 0.1249 0.151 Uiso 1 1 calc R . . C8 C 0.22250(13) 0.7093(4) 0.21471(18) 0.1054(12) Uani 1 1 d . . . H8A H 0.2321 0.7814 0.244 0.158 Uiso 1 1 calc R . . H8B H 0.2298 0.7244 0.1611 0.158 Uiso 1 1 calc R . . H8C H 0.2573 0.6479 0.2338 0.158 Uiso 1 1 calc R . . C9 C 0.06490(11) 0.73082(18) 0.06387(11) 0.0446(5) Uani 1 1 d . . . C10 C 0.01581(14) 0.6663(2) 0.01524(12) 0.0589(6) Uani 1 1 d . . . H10 H -0.0315 0.6431 0.0317 0.071 Uiso 1 1 calc R . . C11 C 0.03512(19) 0.6355(2) -0.05711(14) 0.0772(8) Uani 1 1 d . . . H11 H 0.0008 0.5913 -0.0892 0.093 Uiso 1 1 calc R . . C12 C 0.1030(2) 0.6677(3) -0.08293(15) 0.0827(9) Uani 1 1 d . . . H12 H 0.1161 0.6453 -0.1321 0.099 Uiso 1 1 calc R . . C13 C 0.15102(17) 0.7324(3) -0.03652(15) 0.0758(8) Uani 1 1 d . . . H13 H 0.1978 0.756 -0.054 0.091 Uiso 1 1 calc R . . C14 C 0.13310(13) 0.7644(2) 0.03557(13) 0.0565(6) Uani 1 1 d . . . H14 H 0.1677 0.81 0.0665 0.068 Uiso 1 1 calc R . . C15 C 0.19909(12) 0.9285(3) 0.43229(14) 0.0670(7) Uani 1 1 d . . . H15A H 0.1961 1.0095 0.4121 0.08 Uiso 1 1 calc R . . H15B H 0.2267 0.8793 0.3973 0.08 Uiso 1 1 calc R . . C16 C 0.23798(15) 0.9272(3) 0.51013(16) 0.0755(8) Uani 1 1 d . . . H16A H 0.2642 1.0025 0.521 0.091 Uiso 1 1 calc R . . H16B H 0.2751 0.8627 0.5151 0.091 Uiso 1 1 calc R . . C17 C 0.17641(16) 0.9088(3) 0.56347(14) 0.0785(8) Uani 1 1 d . . . H17A H 0.1807 0.8305 0.5877 0.094 Uiso 1 1 calc R . . H17B H 0.1785 0.9696 0.6036 0.094 Uiso 1 1 calc R . . C18 C 0.10474(14) 0.9186(2) 0.51339(13) 0.0641(7) Uani 1 1 d . . . H18A H 0.0654 0.8667 0.5318 0.077 Uiso 1 1 calc R . . H18B H 0.086 1.0004 0.512 0.077 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 Li 0.0359(17) 0.082(3) 0.0374(17) 0.0016(17) -0.0016(14) -0.0051(16) O 0.0485(8) 0.0894(12) 0.0410(8) -0.0073(8) -0.0001(7) -0.0183(8) N1 0.0270(7) 0.0631(11) 0.0355(9) 0.0005(8) 0.0028(6) -0.0004(7) N2 0.0359(8) 0.0644(11) 0.0325(8) -0.0026(8) 0.0028(7) 0.0056(8) C1 0.0350(10) 0.0590(13) 0.0316(10) -0.0002(9) 0.0021(8) -0.0029(9) C2 0.0535(12) 0.0671(15) 0.0434(12) 0.0015(10) 0.0013(10) -0.0149(11) C3 0.0915(19) 0.0600(15) 0.0484(13) 0.0016(11) -0.0022(12) -0.0150(13) C4 0.0292(9) 0.0668(13) 0.0350(10) 0.0011(10) 0.0059(8) 0.0017(9) C5 0.0471(12) 0.0841(17) 0.0431(12) 0.0016(11) 0.0023(10) 0.0225(11) C6 0.0600(14) 0.0768(17) 0.0498(13) 0.0090(12) -0.0009(11) 0.0164(12) C7 0.150(3) 0.086(2) 0.0619(18) -0.0106(15) -0.0234(18) 0.064(2) C8 0.0411(14) 0.186(4) 0.091(2) 0.043(2) 0.0150(14) 0.0398(18) C9 0.0517(12) 0.0467(12) 0.0356(10) 0.0016(9) 0.0035(9) 0.0107(9) C10 0.0734(16) 0.0595(14) 0.0426(12) 0.0005(11) -0.0045(11) 0.0047(12) C11 0.122(3) 0.0618(16) 0.0441(14) -0.0082(12) -0.0182(15) 0.0183(16) C12 0.129(3) 0.083(2) 0.0379(13) 0.0036(14) 0.0211(16) 0.0418(19) C13 0.093(2) 0.0832(19) 0.0556(15) 0.0136(14) 0.0347(15) 0.0280(16) C14 0.0586(13) 0.0630(14) 0.0501(12) 0.0041(11) 0.0194(11) 0.0101(11) C15 0.0489(13) 0.0960(19) 0.0551(14) 0.0000(13) -0.0035(10) -0.0204(13) C16 0.0659(16) 0.0853(19) 0.0723(18) -0.0052(14) -0.0178(13) -0.0094(14) C17 0.098(2) 0.091(2) 0.0444(14) -0.0035(13) -0.0112(14) -0.0043(16) C18 0.0681(15) 0.0770(17) 0.0482(13) -0.0138(12) 0.0105(11) -0.0130(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Li O 1.909(4) . ? Li N2 1.965(4) 2 ? Li N1 1.983(4) . ? O C15 1.432(3) . ? O C18 1.436(3) . ? N1 C4 1.312(3) . ? N1 C1 1.462(3) . ? N2 C4 1.353(2) . ? N2 C9 1.389(2) . ? N2 Li 1.965(4) 2 ? C1 C2 1.526(3) . ? C1 C1 1.541(3) 2 ? C1 H1 1 . ? C2 C3 1.518(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C3 1.518(5) 2 ? C3 H3A 0.99 . ? C3 H3B 0.99 . ? C4 C5 1.557(3) . ? C5 C7 1.522(4) . ? C5 C6 1.531(3) . ? C5 C8 1.542(3) . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? C7 H7A 0.98 . ? C7 H7B 0.98 . ? C7 H7C 0.98 . ? C8 H8A 0.98 . ? C8 H8B 0.98 . ? C8 H8C 0.98 . ? C9 C10 1.393(3) . ? C9 C14 1.401(3) . ? C10 C11 1.391(3) . ? C10 H10 0.95 . ? C11 C12 1.373(4) . ? C11 H11 0.95 . ? C12 C13 1.361(4) . ? C12 H12 0.95 . ? C13 C14 1.383(3) . ? C13 H13 0.95 . ? C14 H14 0.95 . ? C15 C16 1.497(3) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 C17 1.511(4) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.508(4) . ? C17 H17A 0.99 . ? C17 H17B 0.99 . ? C18 H18A 0.99 . ? C18 H18B 0.99 . ? 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 O Li N2 124.37(18) . 2 ? O Li N1 121.40(19) . . ? N2 Li N1 110.89(17) 2 . ? C15 O C18 105.76(17) . . ? C15 O Li 124.53(16) . . ? C18 O Li 128.16(16) . . ? C4 N1 C1 118.52(16) . . ? C4 N1 Li 124.03(18) . . ? C1 N1 Li 104.77(16) . . ? C4 N2 C9 124.85(16) . . ? C4 N2 Li 115.30(15) . 2 ? C9 N2 Li 119.79(16) . 2 ? N1 C1 C2 110.66(15) . . ? N1 C1 C1 111.33(12) . 2 ? C2 C1 C1 109.39(13) . 2 ? N1 C1 H1 108.5 . . ? C2 C1 H1 108.5 . . ? C1 C1 H1 108.5 2 . ? C3 C2 C1 111.32(18) . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108 . . ? C3 C3 C2 111.20(15) 2 . ? C3 C3 H3A 109.4 2 . ? C2 C3 H3A 109.4 . . ? C3 C3 H3B 109.4 2 . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108 . . ? N1 C4 N2 122.83(18) . . ? N1 C4 C5 114.10(17) . . ? N2 C4 C5 122.76(18) . . ? C7 C5 C6 106.8(2) . . ? C7 C5 C8 111.2(2) . . ? C6 C5 C8 106.4(2) . . ? C7 C5 C4 112.92(19) . . ? C6 C5 C4 110.13(17) . . ? C8 C5 C4 109.2(2) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C10 120.08(19) . . ? N2 C9 C14 122.9(2) . . ? C10 C9 C14 116.68(19) . . ? C11 C10 C9 121.0(2) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C12 C11 C10 121.1(3) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C13 C12 C11 118.6(2) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 C14 121.4(3) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C13 C14 C9 121.2(3) . . ? C13 C14 H14 119.4 . . ? C9 C14 H14 119.4 . . ? O C15 C16 106.43(19) . . ? O C15 H15A 110.4 . . ? C16 C15 H15A 110.4 . . ? O C15 H15B 110.4 . . ? C16 C15 H15B 110.4 . . ? H15A C15 H15B 108.6 . . ? C15 C16 C17 105.2(2) . . ? C15 C16 H16A 110.7 . . ? C17 C16 H16A 110.7 . . ? C15 C16 H16B 110.7 . . ? C17 C16 H16B 110.7 . . ? H16A C16 H16B 108.8 . . ? C18 C17 C16 104.4(2) . . ? C18 C17 H17A 110.9 . . ? C16 C17 H17A 110.9 . . ? C18 C17 H17B 110.9 . . ? C16 C17 H17B 110.9 . . ? H17A C17 H17B 108.9 . . ? O C18 C17 104.47(19) . . ? O C18 H18A 110.9 . . ? C17 C18 H18A 110.9 . . ? O C18 H18B 110.9 . . ? C17 C18 H18B 110.9 . . ? H18A C18 H18B 108.9 . . ? #===END