# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2 _database_code_depnum_ccdc_archive 'CCDC 878332' #TrackingRef '- 878332 878338.txt' _database_code_depnum_ccdc_archive 'CCDC 878332' #TrackingRef 'web_deposit_cif_file_0_PierreThuery_1335341178.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H29 N O2' _chemical_formula_weight 303.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 20.6064(16) _cell_length_b 6.1496(3) _cell_length_c 28.352(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3592.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 133527 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.122 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type none _exptl_special_details 'crystal-to-detector distance 35 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and eight \w scans with 2\% steps (619 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 133527 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3495 _reflns_number_gt 2945 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O and N atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (OH, NH, CH) or 1.5 (CH~3~) times that of the parent atom. In the absence of a suitable anomalous scatterer, the Friedel pairs have been merged. 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^)+(0.0662P)^2^+0.9252P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration unk _refine_ls_number_reflns 3495 _refine_ls_number_parameters 413 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1294 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.198 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.041 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 O1A O 0.34426(13) 0.5849(5) 0.06027(10) 0.0350(7) Uani 1 1 d . . . O2A O 0.35430(13) 0.3221(4) -0.11219(9) 0.0363(6) Uani 1 1 d . . . H2A H 0.3665 0.2712 -0.0814 0.044 Uiso 1 1 d R . . N1A N 0.30134(15) 0.4281(6) -0.02279(11) 0.0304(7) Uani 1 1 d . . . H1A H 0.3225 0.5301 -0.0046 0.036 Uiso 1 1 d R . . C1A C 0.33264(18) 0.3965(7) 0.07651(16) 0.0341(10) Uani 1 1 d . . . C2A C 0.31006(19) 0.2244(6) 0.04835(14) 0.0330(9) Uani 1 1 d . . . H2C H 0.3067 0.0881 0.0624 0.040 Uiso 1 1 calc R . . C3A C 0.29255(18) 0.2418(6) 0.00179(13) 0.0309(9) Uani 1 1 d . . . C4A C 0.3428(2) 0.3579(7) 0.12864(16) 0.0412(10) Uani 1 1 d . . . H4A H 0.3884 0.3605 0.1356 0.062 Uiso 1 1 calc R . . H4B H 0.3252 0.2188 0.1372 0.062 Uiso 1 1 calc R . . H4C H 0.3213 0.4698 0.1463 0.062 Uiso 1 1 calc R . . C5A C 0.2612(2) 0.0564(7) -0.02313(18) 0.0398(10) Uani 1 1 d . . . H5A H 0.2161 0.0879 -0.0280 0.060 Uiso 1 1 calc R . . H5B H 0.2654 -0.0730 -0.0044 0.060 Uiso 1 1 calc R . . H5C H 0.2820 0.0346 -0.0531 0.060 Uiso 1 1 calc R . . C6A C 0.2680(2) 0.4740(6) -0.06625(18) 0.0306(11) Uani 1 1 d . . . C7A C 0.29529(17) 0.4228(7) -0.10956(14) 0.0302(8) Uani 1 1 d . . . C8A C 0.2623(2) 0.4760(7) -0.15077(19) 0.0331(11) Uani 1 1 d . . . C9A C 0.20276(19) 0.5847(7) -0.14663(14) 0.0343(9) Uani 1 1 d . . . H9A H 0.1811 0.6241 -0.1741 0.041 Uiso 1 1 calc R . . C10A C 0.17426(18) 0.6369(6) -0.10331(14) 0.0321(8) Uani 1 1 d . . . C11A C 0.20822(18) 0.5785(7) -0.06319(13) 0.0296(8) Uani 1 1 d . . . H11A H 0.1908 0.6095 -0.0337 0.036 Uiso 1 1 calc R . . C12A C 0.2879(2) 0.4089(7) -0.20037(14) 0.0377(10) Uani 1 1 d . . . C13A C 0.2927(2) 0.1615(7) -0.20320(16) 0.0459(11) Uani 1 1 d . . . H13A H 0.3242 0.1107 -0.1809 0.069 Uiso 1 1 calc R . . H13B H 0.3056 0.1197 -0.2344 0.069 Uiso 1 1 calc R . . H13C H 0.2512 0.0986 -0.1961 0.069 Uiso 1 1 calc R . . C14A C 0.3551(2) 0.5110(8) -0.21001(19) 0.0426(13) Uani 1 1 d . . . H14A H 0.3513 0.6665 -0.2105 0.064 Uiso 1 1 calc R . . H14B H 0.3711 0.4612 -0.2399 0.064 Uiso 1 1 calc R . . H14C H 0.3848 0.4686 -0.1856 0.064 Uiso 1 1 calc R . . C15A C 0.2429(3) 0.4842(8) -0.2402(2) 0.0468(14) Uani 1 1 d . . . H15A H 0.2007 0.4212 -0.2359 0.070 Uiso 1 1 calc R . . H15B H 0.2603 0.4387 -0.2700 0.070 Uiso 1 1 calc R . . H15C H 0.2394 0.6398 -0.2396 0.070 Uiso 1 1 calc R . . C16A C 0.1088(2) 0.7528(7) -0.10228(14) 0.0365(9) Uani 1 1 d . . . C17A C 0.0853(2) 0.7901(8) -0.05156(15) 0.0453(11) Uani 1 1 d . . . H17A H 0.0810 0.6527 -0.0358 0.068 Uiso 1 1 calc R . . H17B H 0.0440 0.8623 -0.0521 0.068 Uiso 1 1 calc R . . H17C H 0.1162 0.8787 -0.0350 0.068 Uiso 1 1 calc R . . C18A C 0.1155(2) 0.9786(7) -0.12576(19) 0.0424(13) Uani 1 1 d . . . H18A H 0.1475 1.0623 -0.1092 0.064 Uiso 1 1 calc R . . H18B H 0.0745 1.0528 -0.1246 0.064 Uiso 1 1 calc R . . H18C H 0.1285 0.9608 -0.1580 0.064 Uiso 1 1 calc R . . C19A C 0.0578(2) 0.6178(8) -0.12825(17) 0.0470(11) Uani 1 1 d . . . H19A H 0.0712 0.5966 -0.1604 0.070 Uiso 1 1 calc R . . H19B H 0.0170 0.6928 -0.1277 0.070 Uiso 1 1 calc R . . H19C H 0.0533 0.4791 -0.1131 0.070 Uiso 1 1 calc R . . O1B O 0.41388(14) 0.0851(5) -0.04453(10) 0.0353(7) Uani 1 1 d . . . O2B O 0.40097(12) -0.1712(4) 0.12852(10) 0.0368(6) Uani 1 1 d . . . H2B H 0.3881 -0.2082 0.0999 0.044 Uiso 1 1 d R . . N1B N 0.45747(15) -0.0708(6) 0.03947(12) 0.0308(7) Uani 1 1 d . . . H1B H 0.4386 0.0395 0.0234 0.037 Uiso 1 1 d R . . C1B C 0.42482(18) -0.1038(6) -0.05955(14) 0.0302(9) Uani 1 1 d . . . C2B C 0.44777(18) -0.2753(6) -0.03143(14) 0.0336(9) Uani 1 1 d . . . H2D H 0.4508 -0.4123 -0.0452 0.040 Uiso 1 1 calc R . . C3B C 0.46612(18) -0.2547(6) 0.01526(14) 0.0309(9) Uani 1 1 d . . . C4B C 0.4141(2) -0.1491(7) -0.11164(14) 0.0404(10) Uani 1 1 d . . . H4D H 0.3687 -0.1720 -0.1174 0.061 Uiso 1 1 calc R . . H4E H 0.4379 -0.2767 -0.1206 0.061 Uiso 1 1 calc R . . H4F H 0.4289 -0.0271 -0.1298 0.061 Uiso 1 1 calc R . . C5B C 0.4969(2) -0.4413(7) 0.04034(17) 0.0410(10) Uani 1 1 d . . . H5D H 0.5430 -0.4192 0.0419 0.061 Uiso 1 1 calc R . . H5E H 0.4880 -0.5735 0.0236 0.061 Uiso 1 1 calc R . . H5F H 0.4797 -0.4514 0.0717 0.061 Uiso 1 1 calc R . . C6B C 0.4891(2) -0.0184(6) 0.08305(17) 0.0263(10) Uani 1 1 d . . . C7B C 0.45978(19) -0.0697(7) 0.12598(15) 0.0336(8) Uani 1 1 d . . . C8B C 0.4922(2) -0.0174(6) 0.16945(18) 0.0320(11) Uani 1 1 d . . . C9B C 0.5509(2) 0.0888(7) 0.16487(14) 0.0351(10) Uani 1 1 d . . . H9B H 0.5719 0.1293 0.1926 0.042 Uiso 1 1 calc R . . C10B C 0.58154(18) 0.1409(6) 0.12260(14) 0.0322(9) Uani 1 1 d . . . C11B C 0.54927(18) 0.0804(7) 0.08166(14) 0.0328(9) Uani 1 1 d . . . H11B H 0.5686 0.1069 0.0526 0.039 Uiso 1 1 calc R . . C12B C 0.4640(2) -0.0813(8) 0.21727(14) 0.0380(10) Uani 1 1 d . . . C13B C 0.4607(2) -0.3319(7) 0.21998(16) 0.0476(11) Uani 1 1 d . . . H13D H 0.5034 -0.3911 0.2157 0.071 Uiso 1 1 calc R . . H13E H 0.4325 -0.3855 0.1957 0.071 Uiso 1 1 calc R . . H13F H 0.4443 -0.3747 0.2503 0.071 Uiso 1 1 calc R . . C14B C 0.3964(3) 0.0131(8) 0.22387(19) 0.0464(14) Uani 1 1 d . . . H14D H 0.3809 -0.0210 0.2549 0.070 Uiso 1 1 calc R . . H14E H 0.3675 -0.0482 0.2008 0.070 Uiso 1 1 calc R . . H14F H 0.3980 0.1681 0.2200 0.070 Uiso 1 1 calc R . . C15B C 0.5070(3) -0.0035(7) 0.2582(2) 0.0466(14) Uani 1 1 d . . . H15D H 0.5127 0.1511 0.2562 0.070 Uiso 1 1 calc R . . H15E H 0.5485 -0.0737 0.2564 0.070 Uiso 1 1 calc R . . H15F H 0.4867 -0.0393 0.2877 0.070 Uiso 1 1 calc R . . C16B C 0.64742(19) 0.2585(7) 0.12202(14) 0.0372(9) Uani 1 1 d . . . C17B C 0.6747(2) 0.2781(9) 0.07225(16) 0.0512(12) Uani 1 1 d . . . H17D H 0.6801 0.1357 0.0590 0.077 Uiso 1 1 calc R . . H17E H 0.7160 0.3506 0.0733 0.077 Uiso 1 1 calc R . . H17F H 0.6453 0.3606 0.0531 0.077 Uiso 1 1 calc R . . C18B C 0.6963(2) 0.1306(8) 0.15202(18) 0.0504(12) Uani 1 1 d . . . H18D H 0.6808 0.1211 0.1839 0.076 Uiso 1 1 calc R . . H18E H 0.7375 0.2039 0.1517 0.076 Uiso 1 1 calc R . . H18F H 0.7013 -0.0130 0.1393 0.076 Uiso 1 1 calc R . . C19B C 0.6399(3) 0.4884(7) 0.1423(2) 0.0468(15) Uani 1 1 d . . . H19D H 0.6108 0.5707 0.1229 0.070 Uiso 1 1 calc R . . H19E H 0.6815 0.5587 0.1431 0.070 Uiso 1 1 calc R . . H19F H 0.6228 0.4795 0.1738 0.070 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 O1A 0.0378(16) 0.0380(18) 0.0292(16) 0.0018(14) -0.0019(12) 0.0002(12) O2A 0.0394(15) 0.0428(15) 0.0268(14) 0.0013(13) 0.0005(12) 0.0099(12) N1A 0.0334(18) 0.0361(18) 0.0215(17) 0.0013(17) -0.0057(14) -0.0036(15) C1A 0.025(2) 0.039(3) 0.038(2) -0.001(2) -0.0044(17) 0.0004(17) C2A 0.037(2) 0.029(2) 0.033(2) 0.0035(17) 0.0009(17) -0.0016(17) C3A 0.029(2) 0.037(2) 0.027(2) -0.0003(18) 0.0013(16) -0.0008(17) C4A 0.052(2) 0.042(2) 0.030(2) 0.003(2) -0.003(2) -0.0036(19) C5A 0.046(2) 0.038(2) 0.036(2) 0.002(2) -0.003(2) -0.008(2) C6A 0.031(2) 0.029(2) 0.032(3) 0.0017(18) -0.0014(19) -0.0032(16) C7A 0.032(2) 0.030(2) 0.029(2) -0.002(2) 0.0012(17) -0.0018(16) C8A 0.036(3) 0.035(2) 0.028(3) 0.0055(18) 0.0027(19) -0.0015(18) C9A 0.037(2) 0.035(2) 0.031(2) 0.0045(18) -0.0023(17) -0.0016(18) C10A 0.036(2) 0.034(2) 0.0266(19) -0.0010(17) 0.0005(17) -0.0018(16) C11A 0.033(2) 0.031(2) 0.025(2) -0.0005(18) 0.0048(16) -0.0032(17) C12A 0.044(3) 0.040(3) 0.029(2) 0.002(2) -0.0017(18) -0.003(2) C13A 0.056(3) 0.048(3) 0.033(2) -0.009(2) -0.006(2) 0.004(2) C14A 0.038(3) 0.056(3) 0.033(3) 0.0017(19) 0.010(2) 0.0017(19) C15A 0.053(3) 0.070(3) 0.018(3) -0.0008(19) 0.005(2) 0.010(2) C16A 0.038(2) 0.041(2) 0.030(2) 0.0022(19) 0.0018(18) 0.0039(17) C17A 0.035(2) 0.062(3) 0.039(2) 0.001(2) 0.0034(19) 0.010(2) C18A 0.042(3) 0.049(3) 0.035(3) 0.0012(19) 0.001(2) 0.006(2) C19A 0.036(2) 0.057(3) 0.048(3) 0.002(2) -0.008(2) 0.004(2) O1B 0.0410(16) 0.0312(17) 0.0338(17) 0.0008(13) -0.0011(13) 0.0034(13) O2B 0.0354(14) 0.0483(16) 0.0268(14) -0.0027(14) -0.0009(13) -0.0085(13) N1B 0.0347(18) 0.0292(17) 0.0286(18) 0.0006(17) -0.0032(14) 0.0009(15) C1B 0.029(2) 0.033(2) 0.029(2) -0.0028(18) 0.0015(17) -0.0043(17) C2B 0.038(2) 0.032(2) 0.030(2) -0.0042(17) -0.0025(18) 0.0002(17) C3B 0.030(2) 0.029(2) 0.034(2) 0.0013(18) 0.0018(17) -0.0034(16) C4B 0.050(2) 0.041(2) 0.030(2) 0.000(2) -0.006(2) 0.0028(19) C5B 0.048(3) 0.041(2) 0.034(2) 0.000(2) -0.002(2) 0.009(2) C6B 0.035(2) 0.028(2) 0.017(2) 0.0016(15) -0.0035(18) 0.0033(16) C7B 0.036(2) 0.035(2) 0.029(2) -0.003(2) -0.0008(18) -0.0050(18) C8B 0.041(3) 0.032(2) 0.023(3) 0.0022(16) -0.0054(19) -0.0004(18) C9B 0.041(2) 0.040(3) 0.024(2) -0.0036(18) -0.0065(17) 0.001(2) C10B 0.036(2) 0.034(2) 0.027(2) 0.0003(18) 0.0008(17) 0.0009(17) C11B 0.034(2) 0.037(2) 0.028(2) 0.0016(19) 0.0004(17) 0.0024(18) C12B 0.044(3) 0.049(3) 0.021(2) 0.004(2) -0.0002(18) -0.006(2) C13B 0.065(3) 0.046(3) 0.032(2) 0.004(2) 0.001(2) -0.007(2) C14B 0.055(3) 0.066(4) 0.018(3) 0.002(2) 0.003(2) 0.002(2) C15B 0.057(3) 0.052(3) 0.030(3) 0.0033(18) -0.005(2) -0.011(2) C16B 0.032(2) 0.047(2) 0.033(2) -0.0016(19) -0.0053(18) -0.0032(17) C17B 0.038(2) 0.070(3) 0.046(3) -0.008(2) 0.007(2) -0.014(2) C18B 0.038(3) 0.050(3) 0.063(3) 0.007(2) -0.007(2) -0.003(2) C19B 0.053(3) 0.042(3) 0.046(4) -0.0008(19) -0.004(2) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C1A 1.270(5) . ? O2A C7A 1.367(5) . ? O2A H2A 0.9612 . ? N1A C3A 1.353(5) . ? N1A C6A 1.439(6) . ? N1A H1A 0.9224 . ? C1A C2A 1.405(6) . ? C1A C4A 1.512(6) . ? C2A C3A 1.373(5) . ? C2A H2C 0.9300 . ? C3A C5A 1.489(6) . ? C4A H4A 0.9600 . ? C4A H4B 0.9600 . ? C4A H4C 0.9600 . ? C5A H5A 0.9600 . ? C5A H5B 0.9600 . ? C5A H5C 0.9600 . ? C6A C7A 1.387(6) . ? C6A C11A 1.392(6) . ? C7A C8A 1.391(7) . ? C8A C9A 1.401(6) . ? C8A C12A 1.558(7) . ? C9A C10A 1.399(6) . ? C9A H9A 0.9300 . ? C10A C11A 1.383(5) . ? C10A C16A 1.527(5) . ? C11A H11A 0.9300 . ? C12A C13A 1.526(6) . ? C12A C15A 1.533(7) . ? C12A C14A 1.545(6) . ? C13A H13A 0.9600 . ? C13A H13B 0.9600 . ? C13A H13C 0.9600 . ? C14A H14A 0.9600 . ? C14A H14B 0.9600 . ? C14A H14C 0.9600 . ? C15A H15A 0.9600 . ? C15A H15B 0.9600 . ? C15A H15C 0.9600 . ? C16A C19A 1.527(6) . ? C16A C17A 1.534(6) . ? C16A C18A 1.546(6) . ? C17A H17A 0.9600 . ? C17A H17B 0.9600 . ? C17A H17C 0.9600 . ? C18A H18A 0.9600 . ? C18A H18B 0.9600 . ? C18A H18C 0.9600 . ? C19A H19A 0.9600 . ? C19A H19B 0.9600 . ? C19A H19C 0.9600 . ? O1B C1B 1.258(5) . ? O2B C7B 1.365(5) . ? O2B H2B 0.8833 . ? N1B C3B 1.335(5) . ? N1B C6B 1.433(6) . ? N1B H1B 0.9040 . ? C1B C2B 1.404(6) . ? C1B C4B 1.519(6) . ? C2B C3B 1.382(6) . ? C2B H2D 0.9300 . ? C3B C5B 1.492(6) . ? C4B H4D 0.9600 . ? C4B H4E 0.9600 . ? C4B H4F 0.9600 . ? C5B H5D 0.9600 . ? C5B H5E 0.9600 . ? C5B H5F 0.9600 . ? C6B C11B 1.382(6) . ? C6B C7B 1.395(6) . ? C7B C8B 1.438(7) . ? C8B C9B 1.381(6) . ? C8B C12B 1.527(7) . ? C9B C10B 1.392(6) . ? C9B H9B 0.9300 . ? C10B C11B 1.389(6) . ? C10B C16B 1.538(5) . ? C11B H11B 0.9300 . ? C12B C14B 1.520(7) . ? C12B C15B 1.538(7) . ? C12B C13B 1.544(7) . ? C13B H13D 0.9600 . ? C13B H13E 0.9600 . ? C13B H13F 0.9600 . ? C14B H14D 0.9600 . ? C14B H14E 0.9600 . ? C14B H14F 0.9600 . ? C15B H15D 0.9600 . ? C15B H15E 0.9600 . ? C15B H15F 0.9600 . ? C16B C17B 1.524(6) . ? C16B C19B 1.534(6) . ? C16B C18B 1.536(6) . ? C17B H17D 0.9600 . ? C17B H17E 0.9600 . ? C17B H17F 0.9600 . ? C18B H18D 0.9600 . ? C18B H18E 0.9600 . ? C18B H18F 0.9600 . ? C19B H19D 0.9600 . ? C19B H19E 0.9600 . ? C19B H19F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7A O2A H2A 109.4 . . ? C3A N1A C6A 122.9(3) . . ? C3A N1A H1A 110.6 . . ? C6A N1A H1A 124.9 . . ? O1A C1A C2A 122.9(4) . . ? O1A C1A C4A 118.1(4) . . ? C2A C1A C4A 118.9(4) . . ? C3A C2A C1A 125.1(4) . . ? C3A C2A H2C 117.4 . . ? C1A C2A H2C 117.4 . . ? N1A C3A C2A 121.7(4) . . ? N1A C3A C5A 117.5(3) . . ? C2A C3A C5A 120.7(4) . . ? C1A C4A H4A 109.5 . . ? C1A C4A H4B 109.5 . . ? H4A C4A H4B 109.5 . . ? C1A C4A H4C 109.5 . . ? H4A C4A H4C 109.5 . . ? H4B C4A H4C 109.5 . . ? C3A C5A H5A 109.5 . . ? C3A C5A H5B 109.5 . . ? H5A C5A H5B 109.5 . . ? C3A C5A H5C 109.5 . . ? H5A C5A H5C 109.5 . . ? H5B C5A H5C 109.5 . . ? C7A C6A C11A 121.2(4) . . ? C7A C6A N1A 121.4(4) . . ? C11A C6A N1A 117.4(4) . . ? O2A C7A C6A 120.8(4) . . ? O2A C7A C8A 119.7(4) . . ? C6A C7A C8A 119.5(4) . . ? C7A C8A C9A 118.0(4) . . ? C7A C8A C12A 122.0(4) . . ? C9A C8A C12A 119.9(4) . . ? C10A C9A C8A 123.4(4) . . ? C10A C9A H9A 118.3 . . ? C8A C9A H9A 118.3 . . ? C11A C10A C9A 116.8(3) . . ? C11A C10A C16A 123.6(3) . . ? C9A C10A C16A 119.7(3) . . ? C10A C11A C6A 121.1(4) . . ? C10A C11A H11A 119.5 . . ? C6A C11A H11A 119.5 . . ? C13A C12A C15A 107.5(4) . . ? C13A C12A C14A 109.7(4) . . ? C15A C12A C14A 106.8(4) . . ? C13A C12A C8A 109.5(3) . . ? C15A C12A C8A 112.3(4) . . ? C14A C12A C8A 110.8(4) . . ? C12A C13A H13A 109.5 . . ? C12A C13A H13B 109.5 . . ? H13A C13A H13B 109.5 . . ? C12A C13A H13C 109.5 . . ? H13A C13A H13C 109.5 . . ? H13B C13A H13C 109.5 . . ? C12A C14A H14A 109.5 . . ? C12A C14A H14B 109.5 . . ? H14A C14A H14B 109.5 . . ? C12A C14A H14C 109.5 . . ? H14A C14A H14C 109.5 . . ? H14B C14A H14C 109.5 . . ? C12A C15A H15A 109.5 . . ? C12A C15A H15B 109.5 . . ? H15A C15A H15B 109.5 . . ? C12A C15A H15C 109.5 . . ? H15A C15A H15C 109.5 . . ? H15B C15A H15C 109.5 . . ? C10A C16A C19A 110.2(3) . . ? C10A C16A C17A 111.5(3) . . ? C19A C16A C17A 108.5(4) . . ? C10A C16A C18A 109.4(3) . . ? C19A C16A C18A 110.0(4) . . ? C17A C16A C18A 107.3(4) . . ? C16A C17A H17A 109.5 . . ? C16A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C16A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? C16A C18A H18A 109.5 . . ? C16A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C16A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C16A C19A H19A 109.5 . . ? C16A C19A H19B 109.5 . . ? H19A C19A H19B 109.5 . . ? C16A C19A H19C 109.5 . . ? H19A C19A H19C 109.5 . . ? H19B C19A H19C 109.5 . . ? C7B O2B H2B 109.6 . . ? C3B N1B C6B 125.0(3) . . ? C3B N1B H1B 115.7 . . ? C6B N1B H1B 117.4 . . ? O1B C1B C2B 124.2(4) . . ? O1B C1B C4B 118.2(4) . . ? C2B C1B C4B 117.6(3) . . ? C3B C2B C1B 124.5(4) . . ? C3B C2B H2D 117.7 . . ? C1B C2B H2D 117.7 . . ? N1B C3B C2B 122.3(4) . . ? N1B C3B C5B 117.6(4) . . ? C2B C3B C5B 120.1(4) . . ? C1B C4B H4D 109.5 . . ? C1B C4B H4E 109.5 . . ? H4D C4B H4E 109.5 . . ? C1B C4B H4F 109.5 . . ? H4D C4B H4F 109.5 . . ? H4E C4B H4F 109.5 . . ? C3B C5B H5D 109.5 . . ? C3B C5B H5E 109.5 . . ? H5D C5B H5E 109.5 . . ? C3B C5B H5F 109.5 . . ? H5D C5B H5F 109.5 . . ? H5E C5B H5F 109.5 . . ? C11B C6B C7B 120.9(4) . . ? C11B C6B N1B 118.8(4) . . ? C7B C6B N1B 120.3(4) . . ? O2B C7B C6B 122.3(4) . . ? O2B C7B C8B 118.0(4) . . ? C6B C7B C8B 119.8(4) . . ? C9B C8B C7B 115.6(4) . . ? C9B C8B C12B 122.6(4) . . ? C7B C8B C12B 121.8(4) . . ? C8B C9B C10B 126.0(4) . . ? C8B C9B H9B 117.0 . . ? C10B C9B H9B 117.0 . . ? C11B C10B C9B 116.2(3) . . ? C11B C10B C16B 122.7(4) . . ? C9B C10B C16B 121.2(4) . . ? C6B C11B C10B 121.6(4) . . ? C6B C11B H11B 119.2 . . ? C10B C11B H11B 119.2 . . ? C14B C12B C8B 111.1(4) . . ? C14B C12B C15B 108.5(4) . . ? C8B C12B C15B 111.7(4) . . ? C14B C12B C13B 109.6(4) . . ? C8B C12B C13B 108.5(4) . . ? C15B C12B C13B 107.3(4) . . ? C12B C13B H13D 109.5 . . ? C12B C13B H13E 109.5 . . ? H13D C13B H13E 109.5 . . ? C12B C13B H13F 109.5 . . ? H13D C13B H13F 109.5 . . ? H13E C13B H13F 109.5 . . ? C12B C14B H14D 109.5 . . ? C12B C14B H14E 109.5 . . ? H14D C14B H14E 109.5 . . ? C12B C14B H14F 109.5 . . ? H14D C14B H14F 109.5 . . ? H14E C14B H14F 109.5 . . ? C12B C15B H15D 109.5 . . ? C12B C15B H15E 109.5 . . ? H15D C15B H15E 109.5 . . ? C12B C15B H15F 109.5 . . ? H15D C15B H15F 109.5 . . ? H15E C15B H15F 109.5 . . ? C17B C16B C19B 108.2(4) . . ? C17B C16B C18B 108.1(4) . . ? C19B C16B C18B 109.3(4) . . ? C17B C16B C10B 111.9(3) . . ? C19B C16B C10B 109.9(3) . . ? C18B C16B C10B 109.4(3) . . ? C16B C17B H17D 109.5 . . ? C16B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C16B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C16B C18B H18D 109.5 . . ? C16B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C16B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C16B C19B H19D 109.5 . . ? C16B C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C16B C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1A H1A O1A 0.92 1.92 2.694(4) 139.9 . O2A H2A O1B 0.96 1.83 2.704(4) 149.5 . N1B H1B O1B 0.90 2.01 2.720(4) 134.0 . O2B H2B O1A 0.88 1.92 2.713(4) 147.9 1_545 data_4 _database_code_depnum_ccdc_archive 'CCDC 878333' #TrackingRef 'web_deposit_cif_file_0_PierreThuery_1335341178.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H63 B F4 N2 O3' _chemical_formula_weight 694.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7837(6) _cell_length_b 11.0362(4) _cell_length_c 19.8110(11) _cell_angle_alpha 101.642(3) _cell_angle_beta 93.665(2) _cell_angle_gamma 117.839(3) _cell_volume 2007.63(19) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 91910 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 25.68 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.149 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and eight \w scans with 2\% steps (611 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 91910 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.68 _reflns_number_total 7587 _reflns_number_gt 6049 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters, with restraints on two bond lengths and displacement parameters for the C atoms of one of the THF molecules. The H atoms bound to O and N atoms were found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (OH, NH, CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. The highest residual electron density peak is located near the badly resolved THF molecule. 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^)+(0.1354P)^2^+0.9254P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7587 _refine_ls_number_parameters 454 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0736 _refine_ls_wR_factor_ref 0.2279 _refine_ls_wR_factor_gt 0.2153 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.059 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.991 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.058 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 1.02335(18) 0.31216(19) 0.21299(9) 0.0468(4) Uani 1 1 d . . . H1 H 1.0673 0.3580 0.2605 0.056 Uiso 1 1 d R . . O2 O 1.1875(2) 0.4397(3) 0.34419(12) 0.0716(6) Uani 1 1 d . . . O3 O 0.3008(6) 0.0870(5) 0.4160(3) 0.167(2) Uani 1 1 d . . . N1 N 0.8749(2) 0.3520(2) 0.32130(10) 0.0391(4) Uani 1 1 d . . . H2 H 0.8989 0.4472 0.3487 0.047 Uiso 1 1 d R . . N2 N 0.7731(2) -0.1228(2) 0.29647(9) 0.0351(4) Uani 1 1 d . . . H3 H 0.7707 -0.1951 0.3149 0.042 Uiso 1 1 d R . . B1 B 0.8160(3) 0.6309(3) 0.40859(15) 0.0447(6) Uani 1 1 d . . . F1 F 0.94356(18) 0.63814(18) 0.39435(10) 0.0653(5) Uani 1 1 d . . . F2 F 0.74859(19) 0.64955(17) 0.35241(8) 0.0609(5) Uani 1 1 d . . . F3 F 0.8398(2) 0.73264(19) 0.46861(8) 0.0688(5) Uani 1 1 d . . . F4 F 0.7301(2) 0.49582(18) 0.41615(10) 0.0654(5) Uani 1 1 d . . . C1 C 0.8969(2) 0.3088(2) 0.19712(12) 0.0372(5) Uani 1 1 d . . . C2 C 0.8209(2) 0.3267(2) 0.24890(11) 0.0354(5) Uani 1 1 d . . . C3 C 0.6946(2) 0.3293(2) 0.23355(11) 0.0356(5) Uani 1 1 d . . . H3A H 0.6485 0.3449 0.2697 0.043 Uiso 1 1 calc R . . C4 C 0.6370(2) 0.3089(2) 0.16534(11) 0.0351(5) Uani 1 1 d . . . C5 C 0.7124(2) 0.2860(2) 0.11321(11) 0.0367(5) Uani 1 1 d . . . H5 H 0.6742 0.2701 0.0668 0.044 Uiso 1 1 calc R . . C6 C 0.8402(2) 0.2858(2) 0.12675(12) 0.0366(5) Uani 1 1 d . . . C7 C 0.4984(2) 0.3103(2) 0.14514(12) 0.0385(5) Uani 1 1 d . . . C8 C 0.4337(3) 0.3367(3) 0.20921(14) 0.0508(6) Uani 1 1 d . . . H8A H 0.5002 0.4270 0.2408 0.076 Uiso 1 1 calc R . . H8B H 0.4132 0.2630 0.2326 0.076 Uiso 1 1 calc R . . H8C H 0.3472 0.3367 0.1945 0.076 Uiso 1 1 calc R . . C9 C 0.5289(3) 0.4302(3) 0.10908(14) 0.0483(6) Uani 1 1 d . . . H9A H 0.5964 0.5198 0.1408 0.072 Uiso 1 1 calc R . . H9B H 0.4418 0.4307 0.0961 0.072 Uiso 1 1 calc R . . H9C H 0.5673 0.4147 0.0679 0.072 Uiso 1 1 calc R . . C10 C 0.3887(3) 0.1671(3) 0.09482(13) 0.0458(6) Uani 1 1 d . . . H10A H 0.3014 0.1680 0.0831 0.069 Uiso 1 1 calc R . . H10B H 0.3708 0.0923 0.1170 0.069 Uiso 1 1 calc R . . H10C H 0.4252 0.1516 0.0529 0.069 Uiso 1 1 calc R . . C11 C 0.9180(3) 0.2633(3) 0.06670(13) 0.0429(5) Uani 1 1 d . . . C12 C 1.0656(3) 0.3959(3) 0.07751(16) 0.0583(7) Uani 1 1 d . . . H12A H 1.0540 0.4774 0.0788 0.088 Uiso 1 1 calc R . . H12B H 1.1128 0.3826 0.0395 0.088 Uiso 1 1 calc R . . H12C H 1.1219 0.4103 0.1209 0.088 Uiso 1 1 calc R . . C13 C 0.9366(3) 0.1333(3) 0.06493(15) 0.0543(7) Uani 1 1 d . . . H13A H 0.9922 0.1478 0.1086 0.081 Uiso 1 1 calc R . . H13B H 0.9845 0.1202 0.0272 0.081 Uiso 1 1 calc R . . H13C H 0.8446 0.0506 0.0579 0.081 Uiso 1 1 calc R . . C14 C 0.8347(3) 0.2392(3) -0.00471(13) 0.0538(7) Uani 1 1 d . . . H14A H 0.7409 0.1589 -0.0119 0.081 Uiso 1 1 calc R . . H14B H 0.8836 0.2214 -0.0410 0.081 Uiso 1 1 calc R . . H14C H 0.8272 0.3221 -0.0060 0.081 Uiso 1 1 calc R . . C15 C 0.8753(3) 0.2565(3) 0.35331(11) 0.0388(5) Uani 1 1 d . . . C16 C 0.8350(2) 0.1193(2) 0.31452(11) 0.0363(5) Uani 1 1 d . . . H16 H 0.8190 0.1028 0.2660 0.044 Uiso 1 1 calc R . . C17 C 0.8162(2) 0.0043(2) 0.34008(11) 0.0372(5) Uani 1 1 d . . . C18 C 0.9216(3) 0.3141(3) 0.43132(12) 0.0517(7) Uani 1 1 d . . . H18A H 0.9541 0.4142 0.4439 0.078 Uiso 1 1 calc R . . H18B H 0.9977 0.2978 0.4463 0.078 Uiso 1 1 calc R . . H18C H 0.8426 0.2670 0.4537 0.078 Uiso 1 1 calc R . . C19 C 0.8367(3) 0.0059(3) 0.41607(13) 0.0526(7) Uani 1 1 d . . . H19A H 0.8112 -0.0879 0.4198 0.079 Uiso 1 1 calc R . . H19B H 0.7774 0.0370 0.4395 0.079 Uiso 1 1 calc R . . H19C H 0.9349 0.0698 0.4375 0.079 Uiso 1 1 calc R . . C20 C 0.7548(2) -0.1559(2) 0.22081(11) 0.0337(5) Uani 1 1 d . . . C21 C 0.6307(2) -0.1765(2) 0.18085(12) 0.0381(5) Uani 1 1 d . . . C22 C 0.6169(3) -0.2142(3) 0.10797(13) 0.0458(6) Uani 1 1 d . . . H22 H 0.5370 -0.2266 0.0801 0.055 Uiso 1 1 calc R . . C23 C 0.7187(3) -0.2333(3) 0.07657(13) 0.0490(6) Uani 1 1 d . . . H23 H 0.7065 -0.2597 0.0279 0.059 Uiso 1 1 calc R . . C24 C 0.8389(3) -0.2136(3) 0.11690(13) 0.0462(6) Uani 1 1 d . . . H24 H 0.9073 -0.2262 0.0951 0.055 Uiso 1 1 calc R . . C25 C 0.8596(2) -0.1750(2) 0.18998(12) 0.0381(5) Uani 1 1 d . . . C26 C 0.5131(3) -0.1648(3) 0.21368(15) 0.0476(6) Uani 1 1 d . . . H26 H 0.5467 -0.1256 0.2644 0.057 Uiso 1 1 calc R . . C27 C 0.3825(3) -0.3125(3) 0.2000(2) 0.0752(10) Uani 1 1 d . . . H27A H 0.3483 -0.3523 0.1505 0.113 Uiso 1 1 calc R . . H27B H 0.3089 -0.3050 0.2222 0.113 Uiso 1 1 calc R . . H27C H 0.4085 -0.3728 0.2189 0.113 Uiso 1 1 calc R . . C28 C 0.4714(4) -0.0675(4) 0.1857(2) 0.0726(9) Uani 1 1 d . . . H28A H 0.5544 0.0237 0.1923 0.109 Uiso 1 1 calc R . . H28B H 0.4021 -0.0566 0.2105 0.109 Uiso 1 1 calc R . . H28C H 0.4314 -0.1083 0.1366 0.109 Uiso 1 1 calc R . . C29 C 0.9931(3) -0.1530(3) 0.23203(14) 0.0465(6) Uani 1 1 d . . . H29 H 0.9866 -0.1318 0.2817 0.056 Uiso 1 1 calc R . . C30 C 1.1232(3) -0.0246(4) 0.2204(2) 0.0730(9) Uani 1 1 d . . . H30A H 1.1342 -0.0443 0.1724 0.109 Uiso 1 1 calc R . . H30B H 1.2070 -0.0059 0.2505 0.109 Uiso 1 1 calc R . . H30C H 1.1099 0.0569 0.2311 0.109 Uiso 1 1 calc R . . C31 C 1.0082(4) -0.2862(4) 0.2149(2) 0.0694(9) Uani 1 1 d . . . H31A H 0.9259 -0.3641 0.2235 0.104 Uiso 1 1 calc R . . H31B H 1.0922 -0.2696 0.2440 0.104 Uiso 1 1 calc R . . H31C H 1.0160 -0.3086 0.1665 0.104 Uiso 1 1 calc R . . C32 C 1.2756(4) 0.3890(5) 0.37051(18) 0.0767(10) Uani 1 1 d . . . H32A H 1.3039 0.3429 0.3324 0.092 Uiso 1 1 calc R . . H32B H 1.2256 0.3218 0.3972 0.092 Uiso 1 1 calc R . . C33 C 1.4030(4) 0.5187(7) 0.4166(2) 0.1083(17) Uani 1 1 d . . . H33A H 1.3934 0.5280 0.4654 0.130 Uiso 1 1 calc R . . H33B H 1.4895 0.5140 0.4109 0.130 Uiso 1 1 calc R . . C34 C 1.4069(5) 0.6384(7) 0.3936(3) 0.1251(19) Uani 1 1 d . . . H34A H 1.4571 0.6548 0.3547 0.150 Uiso 1 1 calc R . . H34B H 1.4519 0.7246 0.4316 0.150 Uiso 1 1 calc R . . C35 C 1.2534(4) 0.5902(4) 0.3720(2) 0.0851(11) Uani 1 1 d . . . H35A H 1.2134 0.6136 0.4118 0.102 Uiso 1 1 calc R . . H35B H 1.2402 0.6345 0.3366 0.102 Uiso 1 1 calc R . . C36 C 0.2825(6) -0.0552(5) 0.4087(3) 0.1133(17) Uani 1 1 d DU . . H36A H 0.3065 -0.0681 0.4537 0.136 Uiso 1 1 calc R . . H36B H 0.1853 -0.1278 0.3873 0.136 Uiso 1 1 calc R . . C37 C 0.3825(7) -0.0589(6) 0.3629(4) 0.131(2) Uani 1 1 d DU . . H37A H 0.3456 -0.0715 0.3146 0.157 Uiso 1 1 calc R . . H37B H 0.4038 -0.1343 0.3655 0.157 Uiso 1 1 calc R . . C38 C 0.5085(7) 0.0814(8) 0.3920(5) 0.172(3) Uani 1 1 d DU . . H38A H 0.5782 0.1032 0.3613 0.207 Uiso 1 1 calc R . . H38B H 0.5532 0.0910 0.4382 0.207 Uiso 1 1 calc R . . C39 C 0.4371(6) 0.1699(5) 0.3944(3) 0.1145(17) Uani 1 1 d DU . . H39A H 0.4943 0.2616 0.4281 0.137 Uiso 1 1 calc R . . H39B H 0.4213 0.1847 0.3487 0.137 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0427(9) 0.0519(10) 0.0440(9) 0.0044(8) 0.0006(7) 0.0259(8) O2 0.0650(13) 0.0760(15) 0.0673(13) -0.0063(11) -0.0179(10) 0.0429(12) O3 0.204(5) 0.128(4) 0.192(5) 0.055(3) 0.090(4) 0.088(4) N1 0.0501(11) 0.0345(10) 0.0319(9) 0.0002(7) -0.0036(8) 0.0249(9) N2 0.0421(10) 0.0361(10) 0.0318(9) 0.0093(8) 0.0061(7) 0.0230(8) B1 0.0585(17) 0.0441(15) 0.0374(14) 0.0094(11) 0.0042(12) 0.0310(13) F1 0.0565(9) 0.0525(9) 0.0807(12) 0.0045(8) 0.0114(8) 0.0272(8) F2 0.0835(12) 0.0494(9) 0.0487(9) 0.0106(7) -0.0089(8) 0.0352(8) F3 0.1044(14) 0.0688(11) 0.0461(9) -0.0023(8) -0.0044(9) 0.0619(11) F4 0.0792(12) 0.0559(10) 0.0751(12) 0.0299(9) 0.0262(9) 0.0378(9) C1 0.0389(11) 0.0291(11) 0.0395(12) 0.0045(9) 0.0024(9) 0.0157(9) C2 0.0441(12) 0.0287(10) 0.0304(11) 0.0044(8) 0.0005(9) 0.0174(9) C3 0.0416(12) 0.0301(10) 0.0328(11) 0.0059(8) 0.0037(9) 0.0172(9) C4 0.0390(11) 0.0277(10) 0.0360(11) 0.0078(8) 0.0029(9) 0.0148(9) C5 0.0433(12) 0.0306(10) 0.0308(11) 0.0076(8) 0.0012(9) 0.0148(9) C6 0.0422(12) 0.0283(10) 0.0353(11) 0.0073(8) 0.0067(9) 0.0146(9) C7 0.0395(12) 0.0352(11) 0.0368(12) 0.0072(9) -0.0007(9) 0.0171(10) C8 0.0482(14) 0.0603(16) 0.0469(14) 0.0100(12) 0.0033(11) 0.0313(13) C9 0.0518(14) 0.0373(12) 0.0533(15) 0.0132(11) -0.0032(11) 0.0210(11) C10 0.0424(13) 0.0385(12) 0.0469(13) 0.0089(10) -0.0046(10) 0.0145(10) C11 0.0484(13) 0.0372(12) 0.0389(12) 0.0070(10) 0.0121(10) 0.0183(10) C12 0.0536(15) 0.0480(15) 0.0598(17) 0.0111(13) 0.0207(13) 0.0141(12) C13 0.0663(17) 0.0464(14) 0.0531(15) 0.0077(12) 0.0168(13) 0.0313(13) C14 0.0648(17) 0.0594(16) 0.0369(13) 0.0109(11) 0.0159(12) 0.0301(14) C15 0.0454(12) 0.0429(12) 0.0305(11) 0.0030(9) 0.0001(9) 0.0271(10) C16 0.0425(12) 0.0405(12) 0.0283(10) 0.0063(9) 0.0026(9) 0.0238(10) C17 0.0423(12) 0.0440(12) 0.0315(11) 0.0077(9) 0.0047(9) 0.0270(10) C18 0.0781(18) 0.0514(15) 0.0310(12) -0.0002(10) -0.0044(11) 0.0421(14) C19 0.0842(19) 0.0511(15) 0.0341(12) 0.0122(11) 0.0086(12) 0.0424(14) C20 0.0388(11) 0.0279(10) 0.0317(11) 0.0059(8) 0.0037(8) 0.0153(9) C21 0.0402(12) 0.0288(11) 0.0413(12) 0.0066(9) -0.0011(9) 0.0158(9) C22 0.0504(14) 0.0368(12) 0.0413(13) 0.0085(10) -0.0084(10) 0.0171(11) C23 0.0645(16) 0.0416(13) 0.0314(12) 0.0066(10) 0.0030(11) 0.0205(12) C24 0.0526(14) 0.0424(13) 0.0380(12) 0.0064(10) 0.0111(10) 0.0202(11) C25 0.0383(11) 0.0344(11) 0.0371(12) 0.0061(9) 0.0064(9) 0.0155(9) C26 0.0391(12) 0.0438(13) 0.0601(16) 0.0079(11) 0.0001(11) 0.0238(11) C27 0.0527(17) 0.0552(18) 0.115(3) 0.0190(18) 0.0266(18) 0.0242(14) C28 0.0659(19) 0.067(2) 0.098(3) 0.0192(18) 0.0010(17) 0.0459(17) C29 0.0389(12) 0.0533(15) 0.0471(14) 0.0066(11) 0.0080(10) 0.0249(11) C30 0.0433(15) 0.069(2) 0.089(2) 0.0151(18) 0.0036(15) 0.0174(15) C31 0.0667(19) 0.067(2) 0.083(2) 0.0136(17) 0.0029(16) 0.0432(17) C32 0.080(2) 0.120(3) 0.0599(19) 0.0236(19) 0.0131(16) 0.074(2) C33 0.061(2) 0.176(5) 0.080(3) 0.031(3) -0.0069(19) 0.055(3) C34 0.081(3) 0.131(5) 0.120(4) 0.023(4) -0.020(3) 0.026(3) C35 0.073(2) 0.074(2) 0.092(3) -0.002(2) -0.0046(19) 0.0341(19) C36 0.150(4) 0.069(2) 0.108(3) 0.023(2) 0.062(3) 0.039(3) C37 0.168(5) 0.079(3) 0.165(5) 0.035(3) 0.096(4) 0.066(3) C38 0.111(4) 0.167(6) 0.228(7) 0.017(5) 0.076(4) 0.067(4) C39 0.135(4) 0.077(3) 0.095(3) 0.017(2) 0.035(3) 0.024(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.361(3) . ? O1 H1 0.9457 . ? O2 C32 1.427(4) . ? O2 C35 1.431(4) . ? O3 C36 1.462(6) . ? O3 C39 1.471(7) . ? N1 C15 1.336(3) . ? N1 C2 1.433(3) . ? N1 H2 0.9815 . ? N2 C17 1.334(3) . ? N2 C20 1.447(3) . ? N2 H3 0.9320 . ? B1 F3 1.376(3) . ? B1 F4 1.386(3) . ? B1 F1 1.390(3) . ? B1 F2 1.392(3) . ? C1 C2 1.393(3) . ? C1 C6 1.409(3) . ? C2 C3 1.390(3) . ? C3 C4 1.379(3) . ? C3 H3A 0.9300 . ? C4 C5 1.409(3) . ? C4 C7 1.530(3) . ? C5 C6 1.388(3) . ? C5 H5 0.9300 . ? C6 C11 1.545(3) . ? C7 C8 1.529(4) . ? C7 C10 1.536(3) . ? C7 C9 1.541(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C14 1.530(4) . ? C11 C13 1.532(4) . ? C11 C12 1.541(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.395(3) . ? C15 C18 1.500(3) . ? C16 C17 1.393(3) . ? C16 H16 0.9300 . ? C17 C19 1.503(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C25 1.397(3) . ? C20 C21 1.406(3) . ? C21 C22 1.397(3) . ? C21 C26 1.506(3) . ? C22 C23 1.374(4) . ? C22 H22 0.9300 . ? C23 C24 1.378(4) . ? C23 H23 0.9300 . ? C24 C25 1.396(3) . ? C24 H24 0.9300 . ? C25 C29 1.505(3) . ? C26 C28 1.525(4) . ? C26 C27 1.531(4) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C31 1.527(4) . ? C29 C30 1.532(4) . ? C29 H29 0.9800 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 C33 1.499(6) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.465(8) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.483(6) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.463(10) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.467(9) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.496(11) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 112.9 . . ? C32 O2 C35 109.7(3) . . ? C36 O3 C39 106.3(4) . . ? C15 N1 C2 126.90(18) . . ? C15 N1 H2 120.5 . . ? C2 N1 H2 111.9 . . ? C17 N2 C20 126.46(18) . . ? C17 N2 H3 118.8 . . ? C20 N2 H3 113.6 . . ? F3 B1 F4 110.8(2) . . ? F3 B1 F1 110.8(2) . . ? F4 B1 F1 106.9(2) . . ? F3 B1 F2 109.7(2) . . ? F4 B1 F2 108.6(2) . . ? F1 B1 F2 109.9(2) . . ? O1 C1 C2 121.6(2) . . ? O1 C1 C6 119.7(2) . . ? C2 C1 C6 118.8(2) . . ? C3 C2 C1 122.0(2) . . ? C3 C2 N1 117.1(2) . . ? C1 C2 N1 120.8(2) . . ? C4 C3 C2 120.7(2) . . ? C4 C3 H3A 119.6 . . ? C2 C3 H3A 119.6 . . ? C3 C4 C5 116.7(2) . . ? C3 C4 C7 123.2(2) . . ? C5 C4 C7 120.15(19) . . ? C6 C5 C4 124.1(2) . . ? C6 C5 H5 117.9 . . ? C4 C5 H5 117.9 . . ? C5 C6 C1 117.6(2) . . ? C5 C6 C11 120.9(2) . . ? C1 C6 C11 121.4(2) . . ? C8 C7 C4 111.85(19) . . ? C8 C7 C10 108.3(2) . . ? C4 C7 C10 109.86(18) . . ? C8 C7 C9 107.8(2) . . ? C4 C7 C9 109.48(19) . . ? C10 C7 C9 109.45(19) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C14 C11 C13 107.9(2) . . ? C14 C11 C12 107.9(2) . . ? C13 C11 C12 109.5(2) . . ? C14 C11 C6 111.5(2) . . ? C13 C11 C6 110.3(2) . . ? C12 C11 C6 109.6(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 C16 120.4(2) . . ? N1 C15 C18 113.0(2) . . ? C16 C15 C18 126.6(2) . . ? C17 C16 C15 127.5(2) . . ? C17 C16 H16 116.3 . . ? C15 C16 H16 116.3 . . ? N2 C17 C16 120.9(2) . . ? N2 C17 C19 113.3(2) . . ? C16 C17 C19 125.8(2) . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 122.3(2) . . ? C25 C20 N2 117.54(19) . . ? C21 C20 N2 120.1(2) . . ? C22 C21 C20 117.2(2) . . ? C22 C21 C26 120.2(2) . . ? C20 C21 C26 122.5(2) . . ? C23 C22 C21 121.5(2) . . ? C23 C22 H22 119.2 . . ? C21 C22 H22 119.2 . . ? C22 C23 C24 120.2(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C25 121.1(2) . . ? C23 C24 H24 119.4 . . ? C25 C24 H24 119.4 . . ? C24 C25 C20 117.7(2) . . ? C24 C25 C29 119.4(2) . . ? C20 C25 C29 122.9(2) . . ? C21 C26 C28 111.9(2) . . ? C21 C26 C27 109.7(2) . . ? C28 C26 C27 109.6(2) . . ? C21 C26 H26 108.5 . . ? C28 C26 H26 108.5 . . ? C27 C26 H26 108.5 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 C31 111.8(2) . . ? C25 C29 C30 109.8(2) . . ? C31 C29 C30 111.6(3) . . ? C25 C29 H29 107.9 . . ? C31 C29 H29 107.9 . . ? C30 C29 H29 107.9 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O2 C32 C33 105.0(3) . . ? O2 C32 H32A 110.7 . . ? C33 C32 H32A 110.7 . . ? O2 C32 H32B 110.7 . . ? C33 C32 H32B 110.7 . . ? H32A C32 H32B 108.8 . . ? C34 C33 C32 105.4(3) . . ? C34 C33 H33A 110.7 . . ? C32 C33 H33A 110.7 . . ? C34 C33 H33B 110.7 . . ? C32 C33 H33B 110.7 . . ? H33A C33 H33B 108.8 . . ? C33 C34 C35 102.6(4) . . ? C33 C34 H34A 111.2 . . ? C35 C34 H34A 111.2 . . ? C33 C34 H34B 111.2 . . ? C35 C34 H34B 111.2 . . ? H34A C34 H34B 109.2 . . ? O2 C35 C34 105.1(4) . . ? O2 C35 H35A 110.7 . . ? C34 C35 H35A 110.7 . . ? O2 C35 H35B 110.7 . . ? C34 C35 H35B 110.7 . . ? H35A C35 H35B 108.8 . . ? C37 C36 O3 103.0(4) . . ? C37 C36 H36A 111.2 . . ? O3 C36 H36A 111.2 . . ? C37 C36 H36B 111.2 . . ? O3 C36 H36B 111.2 . . ? H36A C36 H36B 109.1 . . ? C36 C37 C38 102.2(5) . . ? C36 C37 H37A 111.3 . . ? C38 C37 H37A 111.3 . . ? C36 C37 H37B 111.3 . . ? C38 C37 H37B 111.3 . . ? H37A C37 H37B 109.2 . . ? C37 C38 C39 98.6(5) . . ? C37 C38 H38A 112.0 . . ? C39 C38 H38A 112.0 . . ? C37 C38 H38B 112.0 . . ? C39 C38 H38B 112.0 . . ? H38A C38 H38B 109.7 . . ? O3 C39 C38 104.5(4) . . ? O3 C39 H39A 110.9 . . ? C38 C39 H39A 110.9 . . ? O3 C39 H39B 110.9 . . ? C38 C39 H39B 110.9 . . ? H39A C39 H39B 108.9 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.95 1.81 2.735(3) 165.7 . N1 H2 F1 0.98 1.93 2.907(2) 174.6 . N2 H3 F2 0.93 1.93 2.855(2) 175.1 1_545 data_5 _database_code_depnum_ccdc_archive 'CCDC 878334' #TrackingRef 'web_deposit_cif_file_0_PierreThuery_1335341178.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C80.50 H126 Li4 N4 O6' _chemical_formula_weight 1273.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.1501(14) _cell_length_b 11.5801(10) _cell_length_c 16.331(2) _cell_angle_alpha 74.761(7) _cell_angle_beta 80.257(6) _cell_angle_gamma 81.093(7) _cell_volume 1991.6(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 54371 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 25.68 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.062 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 697 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type none _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and three \w scans with 2\% steps (369 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 54371 _diffrn_reflns_av_R_equivalents 0.0891 _diffrn_reflns_av_sigmaI/netI 0.1198 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.68 _reflns_number_total 7523 _reflns_number_gt 4129 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The solvent pentane molecule is located around an inversion centre and is very badly resolved; a complete molecule with an occupancy factor of 0.25 has been refined with restraints on bond lengths, angles and displacement parameters. The H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. The highest residual electron density peaks are located near the solvent pentane molecule. 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^)+(0.1194P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7523 _refine_ls_number_parameters 469 _refine_ls_number_restraints 44 _refine_ls_R_factor_all 0.1491 _refine_ls_R_factor_gt 0.0774 _refine_ls_wR_factor_ref 0.2338 _refine_ls_wR_factor_gt 0.1983 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.765 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.060 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 0.5405(5) 0.5817(5) 0.9424(4) 0.0413(14) Uani 1 1 d . . . Li2 Li 0.6981(5) 0.7050(4) 0.8023(4) 0.0342(12) Uani 1 1 d . . . O1 O 0.60178(19) 0.41462(18) 0.98223(14) 0.0348(5) Uani 1 1 d . . . O2 O 0.6738(2) 0.68983(19) 0.94148(15) 0.0396(6) Uani 1 1 d . . . O3 O 0.8735(2) 0.7266(2) 0.77422(17) 0.0445(6) Uani 1 1 d . . . N1 N 0.6223(2) 0.5559(2) 0.81696(17) 0.0305(6) Uani 1 1 d . . . N2 N 0.5885(2) 0.8107(2) 0.72375(17) 0.0322(6) Uani 1 1 d . . . C1 C 0.6908(3) 0.3779(3) 0.9260(2) 0.0319(7) Uani 1 1 d . . . C2 C 0.6994(3) 0.4439(3) 0.8399(2) 0.0307(7) Uani 1 1 d . . . C3 C 0.7890(3) 0.4101(3) 0.7780(2) 0.0337(8) Uani 1 1 d . . . H3 H 0.7903 0.4547 0.7216 0.040 Uiso 1 1 calc R . . C4 C 0.8770(3) 0.3118(3) 0.7973(2) 0.0333(7) Uani 1 1 d . . . C5 C 0.8692(3) 0.2481(3) 0.8831(2) 0.0337(8) Uani 1 1 d . . . H5 H 0.9279 0.1827 0.8980 0.040 Uiso 1 1 calc R . . C6 C 0.7793(3) 0.2758(3) 0.9483(2) 0.0319(7) Uani 1 1 d . . . C7 C 0.9811(3) 0.2761(3) 0.7321(2) 0.0392(8) Uani 1 1 d . . . C8 C 0.9730(4) 0.3568(4) 0.6422(3) 0.0633(12) Uani 1 1 d . . . H8A H 0.8970 0.3507 0.6244 0.095 Uiso 1 1 calc R . . H8B H 1.0400 0.3314 0.6031 0.095 Uiso 1 1 calc R . . H8C H 0.9769 0.4388 0.6427 0.095 Uiso 1 1 calc R . . C9 C 0.9787(3) 0.1453(3) 0.7282(3) 0.0490(10) Uani 1 1 d . . . H9A H 0.9853 0.0927 0.7839 0.074 Uiso 1 1 calc R . . H9B H 1.0463 0.1233 0.6882 0.074 Uiso 1 1 calc R . . H9C H 0.9032 0.1383 0.7101 0.074 Uiso 1 1 calc R . . C10 C 1.1045(3) 0.2873(4) 0.7575(3) 0.0551(10) Uani 1 1 d . . . H10A H 1.1059 0.3683 0.7616 0.083 Uiso 1 1 calc R . . H10B H 1.1697 0.2681 0.7150 0.083 Uiso 1 1 calc R . . H10C H 1.1150 0.2326 0.8119 0.083 Uiso 1 1 calc R . . C11 C 0.7803(3) 0.2030(3) 1.0412(2) 0.0348(8) Uani 1 1 d . . . C12 C 0.8003(3) 0.2841(3) 1.0964(2) 0.0407(8) Uani 1 1 d . . . H12A H 0.8736 0.3217 1.0725 0.061 Uiso 1 1 calc R . . H12B H 0.8085 0.2367 1.1535 0.061 Uiso 1 1 calc R . . H12C H 0.7316 0.3450 1.0982 0.061 Uiso 1 1 calc R . . C13 C 0.6602(3) 0.1493(3) 1.0761(2) 0.0435(9) Uani 1 1 d . . . H13A H 0.5933 0.2128 1.0722 0.065 Uiso 1 1 calc R . . H13B H 0.6617 0.1064 1.1349 0.065 Uiso 1 1 calc R . . H13C H 0.6497 0.0949 1.0432 0.065 Uiso 1 1 calc R . . C14 C 0.8834(3) 0.0978(3) 1.0504(2) 0.0429(9) Uani 1 1 d . . . H14A H 0.8753 0.0465 1.0145 0.064 Uiso 1 1 calc R . . H14B H 0.8782 0.0525 1.1090 0.064 Uiso 1 1 calc R . . H14C H 0.9613 0.1288 1.0333 0.064 Uiso 1 1 calc R . . C15 C 0.5197(3) 0.5554(3) 0.7855(2) 0.0339(8) Uani 1 1 d . . . C16 C 0.4508(3) 0.6608(3) 0.7463(2) 0.0351(8) Uani 1 1 d . . . H16 H 0.3699 0.6532 0.7433 0.042 Uiso 1 1 calc R . . C17 C 0.4868(3) 0.7766(3) 0.7107(2) 0.0334(7) Uani 1 1 d . . . C18 C 0.4753(3) 0.4371(3) 0.7907(3) 0.0474(10) Uani 1 1 d . . . H18A H 0.5249 0.3997 0.7486 0.071 Uiso 1 1 calc R . . H18B H 0.3915 0.4509 0.7802 0.071 Uiso 1 1 calc R . . H18C H 0.4812 0.3853 0.8468 0.071 Uiso 1 1 calc R . . C19 C 0.4028(3) 0.8626(3) 0.6524(3) 0.0469(9) Uani 1 1 d . . . H19A H 0.3963 0.9417 0.6622 0.070 Uiso 1 1 calc R . . H19B H 0.3232 0.8355 0.6643 0.070 Uiso 1 1 calc R . . H19C H 0.4358 0.8653 0.5938 0.070 Uiso 1 1 calc R . . C20 C 0.6346(3) 0.9146(3) 0.6652(2) 0.0365(8) Uani 1 1 d . . . C21 C 0.6301(3) 1.0232(3) 0.6893(2) 0.0358(8) Uani 1 1 d . . . C22 C 0.6890(3) 1.1176(3) 0.6324(3) 0.0470(9) Uani 1 1 d . . . H22 H 0.6850 1.1903 0.6475 0.056 Uiso 1 1 calc R . . C23 C 0.7526(4) 1.1048(3) 0.5547(3) 0.0523(10) Uani 1 1 d . . . H23 H 0.7928 1.1675 0.5184 0.063 Uiso 1 1 calc R . . C24 C 0.7560(4) 0.9975(3) 0.5313(3) 0.0521(10) Uani 1 1 d . . . H24 H 0.7989 0.9890 0.4788 0.062 Uiso 1 1 calc R . . C25 C 0.6970(3) 0.9023(3) 0.5844(2) 0.0415(8) Uani 1 1 d . . . C26 C 0.5590(3) 1.0417(3) 0.7730(2) 0.0387(8) Uani 1 1 d . . . H26 H 0.5371 0.9630 0.8076 0.046 Uiso 1 1 calc R . . C27 C 0.4396(3) 1.1250(3) 0.7588(3) 0.0527(10) Uani 1 1 d . . . H27A H 0.4580 1.2016 0.7224 0.079 Uiso 1 1 calc R . . H27B H 0.3969 1.1359 0.8129 0.079 Uiso 1 1 calc R . . H27C H 0.3891 1.0896 0.7322 0.079 Uiso 1 1 calc R . . C28 C 0.6334(4) 1.0906(3) 0.8247(3) 0.0494(10) Uani 1 1 d . . . H28A H 0.7073 1.0373 0.8346 0.074 Uiso 1 1 calc R . . H28B H 0.5857 1.0958 0.8787 0.074 Uiso 1 1 calc R . . H28C H 0.6536 1.1692 0.7933 0.074 Uiso 1 1 calc R . . C29 C 0.7030(4) 0.7863(3) 0.5552(2) 0.0480(9) Uani 1 1 d . . . H29 H 0.6417 0.7381 0.5937 0.058 Uiso 1 1 calc R . . C30 C 0.6726(4) 0.8089(4) 0.4645(3) 0.0602(11) Uani 1 1 d . . . H30A H 0.5898 0.8464 0.4620 0.090 Uiso 1 1 calc R . . H30B H 0.6813 0.7337 0.4485 0.090 Uiso 1 1 calc R . . H30C H 0.7275 0.8609 0.4257 0.090 Uiso 1 1 calc R . . C31 C 0.8276(4) 0.7126(4) 0.5633(3) 0.0674(13) Uani 1 1 d . . . H31A H 0.8902 0.7590 0.5283 0.101 Uiso 1 1 calc R . . H31B H 0.8293 0.6402 0.5448 0.101 Uiso 1 1 calc R . . H31C H 0.8420 0.6920 0.6220 0.101 Uiso 1 1 calc R . . C32 C 0.7739(4) 0.6131(3) 0.9823(3) 0.0545(11) Uani 1 1 d D . . H32A H 0.8307 0.5780 0.9411 0.065 Uiso 1 1 calc R . . H32B H 0.7427 0.5485 1.0283 0.065 Uiso 1 1 calc R . . C33 C 0.8347(5) 0.6901(5) 1.0160(5) 0.098(2) Uani 1 1 d DU . . H33A H 0.8477 0.6515 1.0746 0.118 Uiso 1 1 calc R . . H33B H 0.9137 0.7038 0.9820 0.118 Uiso 1 1 calc R . . C34 C 0.7579(4) 0.8031(4) 1.0125(4) 0.0786(16) Uani 1 1 d . . . H34A H 0.7995 0.8687 0.9746 0.094 Uiso 1 1 calc R . . H34B H 0.7382 0.8186 1.0691 0.094 Uiso 1 1 calc R . . C35 C 0.6445(4) 0.7926(3) 0.9798(3) 0.0479(10) Uani 1 1 d . . . H35A H 0.5773 0.7793 1.0262 0.057 Uiso 1 1 calc R . . H35B H 0.6214 0.8653 0.9374 0.057 Uiso 1 1 calc R . . C36 C 0.9779(3) 0.6373(3) 0.7735(3) 0.0572(11) Uani 1 1 d . . . H36A H 0.9556 0.5643 0.7644 0.069 Uiso 1 1 calc R . . H36B H 1.0107 0.6175 0.8275 0.069 Uiso 1 1 calc R . . C37 C 1.0710(4) 0.6918(4) 0.7009(4) 0.0734(14) Uani 1 1 d . . . H37A H 1.0692 0.6635 0.6503 0.088 Uiso 1 1 calc R . . H37B H 1.1530 0.6717 0.7169 0.088 Uiso 1 1 calc R . . C38 C 1.0320(4) 0.8289(4) 0.6844(3) 0.0703(13) Uani 1 1 d . . . H38A H 1.0974 0.8704 0.6914 0.084 Uiso 1 1 calc R . . H38B H 1.0102 0.8615 0.6271 0.084 Uiso 1 1 calc R . . C39 C 0.9230(3) 0.8412(3) 0.7505(3) 0.0518(10) Uani 1 1 d . . . H39A H 0.9473 0.8585 0.8000 0.062 Uiso 1 1 calc R . . H39B H 0.8626 0.9059 0.7271 0.062 Uiso 1 1 calc R . . C40 C 0.7302(9) 0.467(2) 0.4887(15) 0.083(8) Uani 0.25 1 d PDU . . H40A H 0.7971 0.4540 0.4459 0.125 Uiso 0.25 1 d PR . . H40B H 0.7413 0.5346 0.5095 0.125 Uiso 0.25 1 d PR . . H40C H 0.7271 0.3969 0.5350 0.125 Uiso 0.25 1 d PR . . C41 C 0.6172(8) 0.4732(14) 0.4443(9) 0.064(5) Uani 0.25 1 d PDU . . H41A H 0.6076 0.4064 0.4226 0.077 Uiso 0.25 1 d PR . . H41B H 0.6216 0.5427 0.3973 0.077 Uiso 0.25 1 d PR . . C42 C 0.5000 0.5000 0.5000 0.150(8) Uani 0.50 2 d SPDU . . H42A H 0.4949 0.4373 0.5516 0.225 Uiso 0.25 1 d PR . . H42B H 0.5062 0.5745 0.5132 0.225 Uiso 0.25 1 d PR . . C43 C 0.3785(8) 0.5306(13) 0.4692(10) 0.068(5) Uani 0.25 1 d PDU . . H43A H 0.3840 0.6022 0.4239 0.102 Uiso 0.25 1 d PR . . H43B H 0.3563 0.4681 0.4482 0.102 Uiso 0.25 1 d PR . . C44 C 0.2703(10) 0.557(3) 0.5340(17) 0.108(11) Uani 0.25 1 d PDU . . H44A H 0.2037 0.5840 0.5010 0.163 Uiso 0.25 1 d PR . . H44B H 0.2595 0.4783 0.5704 0.163 Uiso 0.25 1 d PR . . H44C H 0.2722 0.6118 0.5683 0.163 Uiso 0.25 1 d PR . . 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 0.037(3) 0.040(3) 0.046(4) -0.010(3) -0.003(3) -0.004(2) Li2 0.034(3) 0.030(3) 0.039(3) -0.007(2) -0.009(3) -0.005(2) O1 0.0310(12) 0.0344(12) 0.0365(13) -0.0103(10) -0.0008(10) 0.0030(9) O2 0.0408(14) 0.0390(12) 0.0414(14) -0.0134(10) -0.0092(11) -0.0014(10) O3 0.0332(13) 0.0420(13) 0.0591(17) -0.0140(12) -0.0053(12) -0.0044(10) N1 0.0277(14) 0.0280(13) 0.0355(16) -0.0077(11) -0.0064(12) 0.0004(10) N2 0.0312(15) 0.0300(13) 0.0347(16) -0.0075(11) -0.0051(12) -0.0009(11) C1 0.0257(16) 0.0331(16) 0.038(2) -0.0119(14) -0.0049(15) -0.0018(13) C2 0.0304(17) 0.0257(15) 0.0374(19) -0.0091(13) -0.0072(15) -0.0023(13) C3 0.0367(18) 0.0307(16) 0.0344(19) -0.0093(14) -0.0050(15) -0.0036(14) C4 0.0306(17) 0.0356(17) 0.0357(19) -0.0132(14) -0.0043(15) -0.0022(13) C5 0.0276(17) 0.0332(17) 0.041(2) -0.0125(14) -0.0071(15) 0.0022(13) C6 0.0281(17) 0.0331(16) 0.0358(19) -0.0117(14) -0.0035(15) -0.0024(13) C7 0.0370(19) 0.0431(19) 0.037(2) -0.0152(15) -0.0026(16) 0.0039(15) C8 0.069(3) 0.062(3) 0.047(3) -0.012(2) 0.008(2) 0.011(2) C9 0.046(2) 0.047(2) 0.055(3) -0.0228(18) -0.0015(19) 0.0055(17) C10 0.038(2) 0.068(3) 0.063(3) -0.029(2) 0.0054(19) -0.0045(18) C11 0.0318(18) 0.0333(17) 0.037(2) -0.0046(14) -0.0055(15) -0.0016(14) C12 0.0370(19) 0.0464(19) 0.036(2) -0.0100(15) -0.0058(16) 0.0031(15) C13 0.040(2) 0.0413(19) 0.042(2) -0.0034(16) -0.0022(17) -0.0009(16) C14 0.0332(19) 0.0418(19) 0.047(2) -0.0052(16) -0.0061(17) 0.0067(15) C15 0.0329(18) 0.0308(17) 0.038(2) -0.0101(14) -0.0050(15) -0.0013(13) C16 0.0276(17) 0.0339(17) 0.044(2) -0.0091(14) -0.0097(15) -0.0015(13) C17 0.0337(18) 0.0338(17) 0.0329(19) -0.0100(14) -0.0067(15) 0.0014(14) C18 0.046(2) 0.0347(18) 0.066(3) -0.0091(17) -0.021(2) -0.0073(16) C19 0.044(2) 0.043(2) 0.054(2) -0.0060(17) -0.0211(19) -0.0017(16) C20 0.0365(19) 0.0296(16) 0.041(2) -0.0017(14) -0.0121(16) 0.0003(14) C21 0.0365(18) 0.0307(17) 0.038(2) -0.0032(14) -0.0098(16) 0.0000(14) C22 0.050(2) 0.0361(19) 0.054(3) -0.0063(16) -0.009(2) -0.0076(16) C23 0.060(3) 0.046(2) 0.046(2) -0.0019(17) 0.000(2) -0.0161(18) C24 0.060(3) 0.050(2) 0.039(2) -0.0056(17) 0.0061(19) -0.0110(19) C25 0.048(2) 0.0371(18) 0.036(2) -0.0059(15) -0.0043(17) -0.0029(15) C26 0.0381(19) 0.0345(17) 0.042(2) -0.0077(15) -0.0039(16) -0.0042(14) C27 0.049(2) 0.047(2) 0.063(3) -0.0192(19) -0.009(2) 0.0039(17) C28 0.059(2) 0.045(2) 0.046(2) -0.0150(17) -0.0070(19) -0.0075(18) C29 0.061(2) 0.043(2) 0.036(2) -0.0071(16) -0.0010(18) -0.0044(18) C30 0.081(3) 0.053(2) 0.047(3) -0.0128(19) -0.014(2) -0.002(2) C31 0.084(3) 0.061(3) 0.056(3) -0.021(2) -0.016(2) 0.015(2) C32 0.057(2) 0.050(2) 0.060(3) -0.0141(19) -0.027(2) 0.0030(18) C33 0.076(3) 0.082(3) 0.169(6) -0.064(4) -0.071(4) 0.011(3) C34 0.062(3) 0.088(3) 0.115(4) -0.071(3) -0.034(3) 0.009(2) C35 0.057(2) 0.0387(19) 0.055(3) -0.0232(17) -0.014(2) -0.0005(17) C36 0.038(2) 0.046(2) 0.093(3) -0.026(2) -0.016(2) 0.0022(17) C37 0.040(2) 0.096(4) 0.096(4) -0.053(3) -0.002(2) -0.002(2) C38 0.054(3) 0.081(3) 0.074(3) -0.014(3) 0.006(2) -0.026(2) C39 0.041(2) 0.042(2) 0.071(3) -0.0105(18) -0.008(2) -0.0065(16) C40 0.145(18) 0.037(11) 0.074(13) -0.020(10) -0.029(12) -0.002(11) C41 0.114(13) 0.034(7) 0.050(9) -0.017(6) -0.014(9) -0.008(8) C42 0.076(10) 0.110(11) 0.257(19) -0.007(12) -0.001(12) -0.080(9) C43 0.096(9) 0.019(6) 0.089(9) 0.008(6) -0.047(8) -0.005(6) C44 0.147(19) 0.064(15) 0.14(2) -0.012(13) -0.057(14) -0.068(13) _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 1.838(6) 2_667 ? Li1 O1 1.927(6) . ? Li1 O2 2.081(6) . ? Li1 N1 2.174(7) . ? Li1 C15 2.711(7) . ? Li1 C1 2.722(6) . ? Li2 O3 1.970(6) . ? Li2 N2 1.970(6) . ? Li2 N1 1.980(6) . ? Li2 O2 2.206(6) . ? O1 C1 1.333(4) . ? O1 Li1 1.838(6) 2_667 ? O2 C32 1.453(4) . ? O2 C35 1.454(4) . ? O3 C36 1.433(4) . ? O3 C39 1.450(4) . ? N1 C15 1.332(4) . ? N1 C2 1.439(4) . ? N2 C17 1.324(4) . ? N2 C20 1.430(4) . ? C1 C2 1.408(5) . ? C1 C6 1.427(4) . ? C2 C3 1.385(5) . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.397(5) . ? C4 C7 1.521(5) . ? C5 C6 1.400(5) . ? C5 H5 0.9300 . ? C6 C11 1.530(5) . ? C7 C8 1.528(5) . ? C7 C10 1.535(5) . ? C7 C9 1.537(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C13 1.523(5) . ? C11 C12 1.525(5) . ? C11 C14 1.535(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.398(4) . ? C15 C18 1.505(4) . ? C16 C17 1.405(4) . ? C16 H16 0.9300 . ? C17 C19 1.513(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.404(4) . ? C20 C25 1.415(5) . ? C21 C22 1.404(5) . ? C21 C26 1.510(5) . ? C22 C23 1.377(5) . ? C22 H22 0.9300 . ? C23 C24 1.386(5) . ? C23 H23 0.9300 . ? C24 C25 1.389(5) . ? C24 H24 0.9300 . ? C25 C29 1.529(5) . ? C26 C27 1.531(5) . ? C26 C28 1.535(5) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C31 1.521(5) . ? C29 C30 1.522(5) . ? C29 H29 0.9800 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 C33 1.458(5) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.441(6) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.488(5) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.509(7) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.544(6) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.499(6) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 H39A 0.9700 . ? C39 H39B 0.9700 . ? C40 C41 1.541(10) . ? C40 H40A 0.9558 . ? C40 H40B 0.9579 . ? C40 H40C 0.9567 . ? C41 C42 1.501(8) . ? C41 H41A 0.9578 . ? C41 H41B 0.9569 . ? C42 C43 1.484(8) . ? C42 H42A 0.9564 . ? C42 H42B 0.9581 . ? C43 C44 1.514(10) . ? C43 H43A 0.9569 . ? C43 H43B 0.9574 . ? C44 H44A 0.9563 . ? C44 H44B 0.9572 . ? C44 H44C 0.9574 . ? 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 O1 98.7(3) 2_667 . ? O1 Li1 O2 119.8(3) 2_667 . ? O1 Li1 O2 109.6(3) . . ? O1 Li1 N1 145.2(3) 2_667 . ? O1 Li1 N1 84.3(2) . . ? O2 Li1 N1 90.9(2) . . ? O3 Li2 N2 116.5(3) . . ? O3 Li2 N1 127.6(3) . . ? N2 Li2 N1 96.3(2) . . ? O3 Li2 O2 99.8(2) . . ? N2 Li2 O2 124.1(3) . . ? N1 Li2 O2 92.7(2) . . ? C1 O1 Li1 160.3(3) . 2_667 ? C1 O1 Li1 111.9(3) . . ? Li1 O1 Li1 81.3(3) 2_667 . ? C32 O2 C35 106.8(3) . . ? C32 O2 Li1 108.0(2) . . ? C35 O2 Li1 121.1(3) . . ? C32 O2 Li2 112.2(3) . . ? C35 O2 Li2 123.8(2) . . ? Li1 O2 Li2 82.9(2) . . ? C36 O3 C39 105.3(3) . . ? C36 O3 Li2 129.2(3) . . ? C39 O3 Li2 125.4(2) . . ? C15 N1 C2 118.4(2) . . ? C15 N1 Li2 122.6(2) . . ? C2 N1 Li2 116.5(2) . . ? C15 N1 Li1 98.5(3) . . ? C2 N1 Li1 101.2(2) . . ? Li2 N1 Li1 86.1(2) . . ? C17 N2 C20 118.4(3) . . ? C17 N2 Li2 122.2(3) . . ? C20 N2 Li2 117.8(3) . . ? O1 C1 C2 118.5(3) . . ? O1 C1 C6 123.6(3) . . ? C2 C1 C6 117.9(3) . . ? C3 C2 C1 121.4(3) . . ? C3 C2 N1 118.8(3) . . ? C1 C2 N1 119.5(3) . . ? C2 C3 C4 122.4(3) . . ? C2 C3 H3 118.8 . . ? C4 C3 H3 118.8 . . ? C3 C4 C5 115.9(3) . . ? C3 C4 C7 123.9(3) . . ? C5 C4 C7 120.2(3) . . ? C4 C5 C6 124.6(3) . . ? C4 C5 H5 117.7 . . ? C6 C5 H5 117.7 . . ? C5 C6 C1 117.8(3) . . ? C5 C6 C11 120.9(3) . . ? C1 C6 C11 121.2(3) . . ? C4 C7 C8 112.0(3) . . ? C4 C7 C10 109.8(3) . . ? C8 C7 C10 107.7(3) . . ? C4 C7 C9 110.4(3) . . ? C8 C7 C9 108.0(3) . . ? C10 C7 C9 109.0(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13 C11 C12 109.5(3) . . ? C13 C11 C6 110.9(3) . . ? C12 C11 C6 109.7(3) . . ? C13 C11 C14 107.0(3) . . ? C12 C11 C14 107.3(3) . . ? C6 C11 C14 112.3(3) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 C16 122.9(3) . . ? N1 C15 C18 119.4(3) . . ? C16 C15 C18 117.6(3) . . ? C15 C16 C17 129.0(3) . . ? C15 C16 H16 115.5 . . ? C17 C16 H16 115.5 . . ? N2 C17 C16 123.9(3) . . ? N2 C17 C19 120.4(3) . . ? C16 C17 C19 115.7(3) . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 119.8(3) . . ? C21 C20 N2 121.6(3) . . ? C25 C20 N2 118.2(3) . . ? C22 C21 C20 119.0(3) . . ? C22 C21 C26 119.7(3) . . ? C20 C21 C26 121.2(3) . . ? C23 C22 C21 121.3(3) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C22 C23 C24 119.3(3) . . ? C22 C23 H23 120.3 . . ? C24 C23 H23 120.3 . . ? C23 C24 C25 121.6(4) . . ? C23 C24 H24 119.2 . . ? C25 C24 H24 119.2 . . ? C24 C25 C20 118.9(3) . . ? C24 C25 C29 119.4(3) . . ? C20 C25 C29 121.6(3) . . ? C21 C26 C27 111.3(3) . . ? C21 C26 C28 113.0(3) . . ? C27 C26 C28 109.6(3) . . ? C21 C26 H26 107.6 . . ? C27 C26 H26 107.6 . . ? C28 C26 H26 107.6 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C31 C29 C30 110.3(3) . . ? C31 C29 C25 110.9(3) . . ? C30 C29 C25 112.9(3) . . ? C31 C29 H29 107.5 . . ? C30 C29 H29 107.5 . . ? C25 C29 H29 107.5 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O2 C32 C33 106.5(3) . . ? O2 C32 H32A 110.4 . . ? C33 C32 H32A 110.4 . . ? O2 C32 H32B 110.4 . . ? C33 C32 H32B 110.4 . . ? H32A C32 H32B 108.6 . . ? C34 C33 C32 108.4(4) . . ? C34 C33 H33A 110.0 . . ? C32 C33 H33A 110.0 . . ? C34 C33 H33B 110.0 . . ? C32 C33 H33B 110.0 . . ? H33A C33 H33B 108.4 . . ? C33 C34 C35 106.8(3) . . ? C33 C34 H34A 110.4 . . ? C35 C34 H34A 110.4 . . ? C33 C34 H34B 110.4 . . ? C35 C34 H34B 110.4 . . ? H34A C34 H34B 108.6 . . ? O2 C35 C34 105.7(3) . . ? O2 C35 H35A 110.6 . . ? C34 C35 H35A 110.6 . . ? O2 C35 H35B 110.6 . . ? C34 C35 H35B 110.6 . . ? H35A C35 H35B 108.7 . . ? O3 C36 C37 106.1(3) . . ? O3 C36 H36A 110.5 . . ? C37 C36 H36A 110.5 . . ? O3 C36 H36B 110.5 . . ? C37 C36 H36B 110.5 . . ? H36A C36 H36B 108.7 . . ? C36 C37 C38 104.5(3) . . ? C36 C37 H37A 110.9 . . ? C38 C37 H37A 110.9 . . ? C36 C37 H37B 110.9 . . ? C38 C37 H37B 110.9 . . ? H37A C37 H37B 108.9 . . ? C39 C38 C37 104.3(4) . . ? C39 C38 H38A 110.9 . . ? C37 C38 H38A 110.9 . . ? C39 C38 H38B 110.9 . . ? C37 C38 H38B 110.9 . . ? H38A C38 H38B 108.9 . . ? O3 C39 C38 105.9(3) . . ? O3 C39 H39A 110.6 . . ? C38 C39 H39A 110.6 . . ? O3 C39 H39B 110.6 . . ? C38 C39 H39B 110.6 . . ? H39A C39 H39B 108.7 . . ? C41 C40 H40A 103.0 . . ? C41 C40 H40B 119.6 . . ? H40A C40 H40B 109.6 . . ? C41 C40 H40C 105.3 . . ? H40A C40 H40C 109.3 . . ? H40B C40 H40C 109.6 . . ? C42 C41 C40 111.8(9) . . ? C42 C41 H41A 107.1 . . ? C40 C41 H41A 119.2 . . ? C42 C41 H41B 104.8 . . ? C40 C41 H41B 105.1 . . ? H41A C41 H41B 107.9 . . ? C43 C42 C41 123.6(7) . . ? C43 C42 H42A 109.3 . . ? C41 C42 H42A 108.7 . . ? C43 C42 H42B 99.0 . . ? C41 C42 H42B 105.7 . . ? H42A C42 H42B 109.6 . . ? C42 C43 C44 116.4(10) . . ? C42 C43 H43A 106.3 . . ? C44 C43 H43A 107.0 . . ? C42 C43 H43B 112.9 . . ? C44 C43 H43B 104.5 . . ? H43A C43 H43B 109.6 . . ? C43 C44 H44A 103.9 . . ? C43 C44 H44B 102.6 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 121.3 . . ? H44A C44 H44C 109.4 . . ? H44B C44 H44C 109.6 . . ? data_6 _database_code_depnum_ccdc_archive 'CCDC 878335' #TrackingRef 'web_deposit_cif_file_0_PierreThuery_1335341178.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C68 H94 Cl4 N4 O2 Zr2' _chemical_formula_weight 1323.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3601(5) _cell_length_b 12.7048(9) _cell_length_c 16.1239(12) _cell_angle_alpha 73.543(3) _cell_angle_beta 77.583(4) _cell_angle_gamma 79.236(4) _cell_volume 1779.6(2) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 75556 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 25.68 _exptl_crystal_description lath _exptl_crystal_colour 'translucent light orange' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 694 _exptl_absorpt_coefficient_mu 0.485 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.794 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 35 mm' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and ten \w scans with 2\% steps (721 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 75556 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.68 _reflns_number_total 6756 _reflns_number_gt 5610 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (CH) or 1.5 (CH~3~) times that of the parent atom. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1343P)^2^+3.5107P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6756 _refine_ls_number_parameters 373 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0877 _refine_ls_R_factor_gt 0.0767 _refine_ls_wR_factor_ref 0.2240 _refine_ls_wR_factor_gt 0.2167 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.793 _refine_diff_density_min -1.143 _refine_diff_density_rms 0.152 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 Zr Zr 0.41662(5) 0.58225(4) 0.09481(3) 0.0270(2) Uani 1 1 d . . . Cl1 Cl 0.37959(13) 0.57502(10) -0.05704(8) 0.0320(3) Uani 1 1 d . . . Cl2 Cl 0.59085(15) 0.71336(11) 0.06068(10) 0.0413(3) Uani 1 1 d . . . O1 O 0.4652(4) 0.5133(3) 0.2134(2) 0.0296(7) Uani 1 1 d . . . N1 N 0.2564(4) 0.4642(3) 0.1617(3) 0.0287(9) Uani 1 1 d . . . N2 N 0.2124(4) 0.6979(3) 0.0894(3) 0.0303(9) Uani 1 1 d . . . C1 C 0.4231(5) 0.4133(4) 0.2604(3) 0.0293(10) Uani 1 1 d . . . C2 C 0.3088(5) 0.3822(4) 0.2324(3) 0.0300(10) Uani 1 1 d . . . C3 C 0.2536(6) 0.2831(4) 0.2795(3) 0.0316(11) Uani 1 1 d . . . H3 H 0.1765 0.2621 0.2625 0.038 Uiso 1 1 calc R . . C4 C 0.3136(6) 0.2164(4) 0.3514(3) 0.0348(11) Uani 1 1 d . . . C5 C 0.4305(6) 0.2491(4) 0.3755(3) 0.0347(11) Uani 1 1 d . . . H5 H 0.4716 0.2028 0.4229 0.042 Uiso 1 1 calc R . . C6 C 0.4877(6) 0.3470(5) 0.3319(3) 0.0344(11) Uani 1 1 d . . . C7 C 0.2592(7) 0.1058(5) 0.4039(4) 0.0401(13) Uani 1 1 d . . . C8 C 0.3821(8) 0.0102(5) 0.3943(4) 0.0505(15) Uani 1 1 d . . . H8A H 0.4121 0.0109 0.3334 0.076 Uiso 1 1 calc R . . H8B H 0.3467 -0.0587 0.4263 0.076 Uiso 1 1 calc R . . H8C H 0.4649 0.0184 0.4172 0.076 Uiso 1 1 calc R . . C9 C 0.1248(7) 0.0861(5) 0.3738(4) 0.0493(15) Uani 1 1 d . . . H9A H 0.1513 0.0808 0.3140 0.074 Uiso 1 1 calc R . . H9B H 0.0473 0.1466 0.3778 0.074 Uiso 1 1 calc R . . H9C H 0.0912 0.0184 0.4105 0.074 Uiso 1 1 calc R . . C10 C 0.2140(8) 0.1067(6) 0.5024(4) 0.0523(16) Uani 1 1 d . . . H10A H 0.1818 0.0372 0.5360 0.079 Uiso 1 1 calc R . . H10B H 0.1351 0.1657 0.5087 0.079 Uiso 1 1 calc R . . H10C H 0.2973 0.1178 0.5233 0.079 Uiso 1 1 calc R . . C11 C 0.6150(6) 0.3819(5) 0.3597(3) 0.0391(12) Uani 1 1 d . . . C12 C 0.6644(8) 0.3000(6) 0.4409(4) 0.0556(17) Uani 1 1 d . . . H12A H 0.5839 0.2961 0.4895 0.083 Uiso 1 1 calc R . . H12B H 0.7456 0.3242 0.4547 0.083 Uiso 1 1 calc R . . H12C H 0.6947 0.2281 0.4297 0.083 Uiso 1 1 calc R . . C13 C 0.5689(7) 0.4959(6) 0.3795(4) 0.0510(15) Uani 1 1 d . . . H13A H 0.4769 0.4959 0.4196 0.076 Uiso 1 1 calc R . . H13B H 0.5577 0.5515 0.3259 0.076 Uiso 1 1 calc R . . H13C H 0.6434 0.5116 0.4052 0.076 Uiso 1 1 calc R . . C14 C 0.7481(6) 0.3866(6) 0.2847(4) 0.0441(14) Uani 1 1 d . . . H14A H 0.8302 0.4046 0.3024 0.066 Uiso 1 1 calc R . . H14B H 0.7232 0.4423 0.2337 0.066 Uiso 1 1 calc R . . H14C H 0.7742 0.3159 0.2711 0.066 Uiso 1 1 calc R . . C15 C 0.1344(5) 0.4660(4) 0.1286(3) 0.0307(11) Uani 1 1 d . . . C16 C 0.0569(6) 0.5671(5) 0.0899(3) 0.0344(11) Uani 1 1 d . . . H16 H -0.0220 0.5620 0.0652 0.041 Uiso 1 1 calc R . . C17 C 0.0815(6) 0.6742(5) 0.0831(3) 0.0353(11) Uani 1 1 d . . . C18 C 0.0775(6) 0.3624(5) 0.1302(4) 0.0380(12) Uani 1 1 d . . . H18A H 0.1589 0.3087 0.1155 0.057 Uiso 1 1 calc R . . H18B H 0.0123 0.3793 0.0883 0.057 Uiso 1 1 calc R . . H18C H 0.0249 0.3328 0.1878 0.057 Uiso 1 1 calc R . . C19 C -0.0447(6) 0.7654(5) 0.0664(4) 0.0447(13) Uani 1 1 d . . . H19A H -0.0193 0.8329 0.0712 0.067 Uiso 1 1 calc R . . H19B H -0.1310 0.7461 0.1088 0.067 Uiso 1 1 calc R . . H19C H -0.0644 0.7754 0.0084 0.067 Uiso 1 1 calc R . . C20 C 0.2302(5) 0.8111(4) 0.0843(3) 0.0328(11) Uani 1 1 d . . . C21 C 0.2603(5) 0.8867(4) 0.0010(3) 0.0336(11) Uani 1 1 d . . . C22 C 0.2946(6) 0.9889(5) -0.0004(4) 0.0401(13) Uani 1 1 d . . . H22 H 0.3161 1.0394 -0.0542 0.048 Uiso 1 1 calc R . . C23 C 0.2978(6) 1.0181(5) 0.0750(4) 0.0445(14) Uani 1 1 d . . . H23 H 0.3223 1.0868 0.0721 0.053 Uiso 1 1 calc R . . C24 C 0.2635(7) 0.9423(5) 0.1563(4) 0.0430(13) Uani 1 1 d . . . H24 H 0.2648 0.9618 0.2075 0.052 Uiso 1 1 calc R . . C25 C 0.2281(6) 0.8404(4) 0.1621(4) 0.0361(12) Uani 1 1 d . . . C26 C 0.2567(6) 0.8613(4) -0.0848(3) 0.0370(12) Uani 1 1 d . . . H26 H 0.2249 0.7881 -0.0711 0.044 Uiso 1 1 calc R . . C27 C 0.4104(7) 0.8573(5) -0.1430(4) 0.0435(14) Uani 1 1 d . . . H27A H 0.4060 0.8345 -0.1942 0.065 Uiso 1 1 calc R . . H27B H 0.4799 0.8055 -0.1105 0.065 Uiso 1 1 calc R . . H27C H 0.4412 0.9296 -0.1605 0.065 Uiso 1 1 calc R . . C28 C 0.1475(7) 0.9451(5) -0.1368(4) 0.0507(15) Uani 1 1 d . . . H28A H 0.1809 1.0165 -0.1553 0.076 Uiso 1 1 calc R . . H28B H 0.0520 0.9497 -0.1004 0.076 Uiso 1 1 calc R . . H28C H 0.1411 0.9219 -0.1875 0.076 Uiso 1 1 calc R . . C29 C 0.1864(7) 0.7633(5) 0.2520(4) 0.0458(14) Uani 1 1 d . . . H29 H 0.1833 0.6904 0.2435 0.055 Uiso 1 1 calc R . . C30 C 0.0310(9) 0.8054(7) 0.2940(5) 0.079(3) Uani 1 1 d . . . H30A H 0.0276 0.8805 0.2962 0.119 Uiso 1 1 calc R . . H30B H 0.0073 0.7598 0.3524 0.119 Uiso 1 1 calc R . . H30C H -0.0392 0.8021 0.2595 0.119 Uiso 1 1 calc R . . C31 C 0.2973(12) 0.7489(6) 0.3104(5) 0.078(3) Uani 1 1 d . . . H31A H 0.3946 0.7310 0.2794 0.117 Uiso 1 1 calc R . . H31B H 0.2762 0.6901 0.3620 0.117 Uiso 1 1 calc R . . H31C H 0.2921 0.8165 0.3271 0.117 Uiso 1 1 calc R . . C32 C 0.1292(10) 0.4299(8) 0.5200(7) 0.082(3) Uani 1 1 d . . . H32 H 0.2154 0.3837 0.5329 0.098 Uiso 1 1 calc R . . C33 C 0.0968(9) 0.4569(7) 0.4388(6) 0.074(2) Uani 1 1 d . . . H33 H 0.1616 0.4277 0.3959 0.088 Uiso 1 1 calc R . . C34 C -0.0316(12) 0.5280(9) 0.4158(7) 0.090(3) Uani 1 1 d . . . H34 H -0.0503 0.5461 0.3587 0.108 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 Zr 0.0262(3) 0.0293(3) 0.0227(3) -0.00801(19) 0.00237(18) -0.00230(19) Cl1 0.0322(6) 0.0350(6) 0.0244(6) -0.0100(5) -0.0009(5) 0.0053(5) Cl2 0.0361(7) 0.0392(7) 0.0467(8) -0.0066(6) -0.0032(6) -0.0116(6) O1 0.0310(17) 0.0337(18) 0.0228(16) -0.0097(14) -0.0004(14) -0.0023(14) N1 0.028(2) 0.031(2) 0.024(2) -0.0087(17) 0.0031(16) -0.0033(17) N2 0.029(2) 0.033(2) 0.025(2) -0.0075(17) 0.0035(16) -0.0011(17) C1 0.032(2) 0.032(2) 0.019(2) -0.0066(19) 0.0062(19) -0.006(2) C2 0.029(2) 0.032(3) 0.025(2) -0.008(2) 0.0038(19) -0.003(2) C3 0.030(2) 0.034(3) 0.029(3) -0.011(2) 0.004(2) -0.004(2) C4 0.038(3) 0.034(3) 0.026(2) -0.005(2) 0.004(2) -0.003(2) C5 0.036(3) 0.036(3) 0.025(2) -0.003(2) 0.000(2) -0.001(2) C6 0.035(3) 0.042(3) 0.024(2) -0.008(2) 0.000(2) -0.006(2) C7 0.048(3) 0.036(3) 0.030(3) -0.003(2) 0.002(2) -0.009(2) C8 0.064(4) 0.036(3) 0.043(3) -0.003(3) -0.003(3) -0.003(3) C9 0.058(4) 0.038(3) 0.048(4) -0.001(3) -0.005(3) -0.014(3) C10 0.065(4) 0.051(4) 0.032(3) -0.002(3) 0.008(3) -0.019(3) C11 0.038(3) 0.052(3) 0.027(3) -0.009(2) -0.004(2) -0.007(2) C12 0.055(4) 0.071(4) 0.040(3) -0.003(3) -0.015(3) -0.015(3) C13 0.051(4) 0.070(4) 0.041(3) -0.027(3) -0.006(3) -0.012(3) C14 0.034(3) 0.062(4) 0.036(3) -0.011(3) -0.001(2) -0.012(3) C15 0.029(2) 0.039(3) 0.024(2) -0.012(2) 0.0056(19) -0.009(2) C16 0.028(2) 0.046(3) 0.029(3) -0.011(2) 0.000(2) -0.008(2) C17 0.029(3) 0.046(3) 0.030(3) -0.014(2) 0.002(2) -0.005(2) C18 0.041(3) 0.042(3) 0.034(3) -0.011(2) -0.007(2) -0.009(2) C19 0.035(3) 0.045(3) 0.051(3) -0.013(3) -0.006(3) 0.003(2) C20 0.028(2) 0.034(3) 0.033(3) -0.012(2) 0.002(2) 0.002(2) C21 0.027(2) 0.034(3) 0.032(3) -0.008(2) 0.004(2) 0.004(2) C22 0.038(3) 0.034(3) 0.038(3) -0.005(2) 0.007(2) -0.002(2) C23 0.042(3) 0.034(3) 0.055(4) -0.013(3) 0.000(3) -0.006(2) C24 0.046(3) 0.043(3) 0.042(3) -0.019(3) -0.004(3) -0.003(3) C25 0.036(3) 0.033(3) 0.034(3) -0.013(2) 0.000(2) 0.007(2) C26 0.041(3) 0.032(3) 0.029(3) -0.005(2) 0.003(2) 0.001(2) C27 0.047(3) 0.042(3) 0.031(3) -0.007(2) 0.010(2) -0.001(3) C28 0.055(4) 0.048(4) 0.043(3) -0.012(3) -0.006(3) 0.005(3) C29 0.066(4) 0.035(3) 0.034(3) -0.013(2) -0.002(3) 0.001(3) C30 0.081(5) 0.067(5) 0.053(4) 0.005(4) 0.027(4) 0.008(4) C31 0.137(8) 0.048(4) 0.060(5) -0.015(4) -0.048(5) -0.001(4) C32 0.069(5) 0.086(6) 0.110(8) -0.050(6) -0.011(5) -0.023(5) C33 0.051(4) 0.084(6) 0.094(6) -0.056(5) 0.026(4) -0.021(4) C34 0.113(8) 0.096(7) 0.082(6) -0.043(5) -0.003(6) -0.051(6) _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 Zr O1 1.976(3) . ? Zr N2 2.184(4) . ? Zr N1 2.211(4) . ? Zr Cl2 2.4179(14) . ? Zr Cl1 2.5744(13) . ? Zr Cl1 2.6016(12) 2_665 ? Cl1 Zr 2.6016(12) 2_665 ? O1 C1 1.364(6) . ? N1 C15 1.353(7) . ? N1 C2 1.415(6) . ? N2 C17 1.346(7) . ? N2 C20 1.456(7) . ? C1 C6 1.401(7) . ? C1 C2 1.405(7) . ? C2 C3 1.401(7) . ? C3 C4 1.387(7) . ? C3 H3 0.9300 . ? C4 C5 1.401(8) . ? C4 C7 1.536(7) . ? C5 C6 1.385(8) . ? C5 H5 0.9300 . ? C6 C11 1.535(8) . ? C7 C8 1.526(8) . ? C7 C9 1.527(9) . ? C7 C10 1.556(8) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.523(8) . ? C11 C13 1.534(9) . ? C11 C14 1.536(8) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.400(7) . ? C15 C18 1.503(7) . ? C16 C17 1.392(8) . ? C16 H16 0.9300 . ? C17 C19 1.502(8) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C25 1.401(8) . ? C20 C21 1.419(7) . ? C21 C22 1.387(8) . ? C21 C26 1.516(8) . ? C22 C23 1.376(9) . ? C22 H22 0.9300 . ? C23 C24 1.402(9) . ? C23 H23 0.9300 . ? C24 C25 1.368(8) . ? C24 H24 0.9300 . ? C25 C29 1.520(8) . ? C26 C28 1.529(8) . ? C26 C27 1.540(7) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C31 1.499(10) . ? C29 C30 1.533(10) . ? C29 H29 0.9800 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 C33 1.342(14) . ? C32 C34 1.385(13) 2_566 ? C32 H32 0.9300 . ? C33 C34 1.412(14) . ? C33 H33 0.9300 . ? C34 C32 1.385(13) 2_566 ? C34 H34 0.9300 . ? 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 Zr N2 115.57(14) . . ? O1 Zr N1 73.80(15) . . ? N2 Zr N1 80.91(15) . . ? O1 Zr Cl2 92.86(11) . . ? N2 Zr Cl2 99.19(12) . . ? N1 Zr Cl2 164.92(11) . . ? O1 Zr Cl1 153.01(11) . . ? N2 Zr Cl1 83.10(11) . . ? N1 Zr Cl1 91.39(11) . . ? Cl2 Zr Cl1 103.62(5) . . ? O1 Zr Cl1 81.44(10) . 2_665 ? N2 Zr Cl1 158.36(12) . 2_665 ? N1 Zr Cl1 92.07(11) . 2_665 ? Cl2 Zr Cl1 92.85(5) . 2_665 ? Cl1 Zr Cl1 76.59(4) . 2_665 ? Zr Cl1 Zr 103.41(4) . 2_665 ? C1 O1 Zr 120.7(3) . . ? C15 N1 C2 126.5(4) . . ? C15 N1 Zr 121.3(3) . . ? C2 N1 Zr 111.6(3) . . ? C17 N2 C20 120.2(4) . . ? C17 N2 Zr 125.6(4) . . ? C20 N2 Zr 114.0(3) . . ? O1 C1 C6 122.7(5) . . ? O1 C1 C2 114.8(4) . . ? C6 C1 C2 122.5(5) . . ? C3 C2 C1 118.8(5) . . ? C3 C2 N1 128.4(5) . . ? C1 C2 N1 112.6(4) . . ? C4 C3 C2 120.1(5) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 119.1(5) . . ? C3 C4 C7 122.1(5) . . ? C5 C4 C7 118.8(5) . . ? C6 C5 C4 123.1(5) . . ? C6 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C5 C6 C1 116.4(5) . . ? C5 C6 C11 122.4(5) . . ? C1 C6 C11 121.3(5) . . ? C8 C7 C9 108.4(5) . . ? C8 C7 C4 109.9(5) . . ? C9 C7 C4 112.3(5) . . ? C8 C7 C10 109.4(5) . . ? C9 C7 C10 107.8(5) . . ? C4 C7 C10 108.9(5) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C13 108.1(5) . . ? C12 C11 C6 112.5(5) . . ? C13 C11 C6 110.4(5) . . ? C12 C11 C14 107.3(5) . . ? C13 C11 C14 109.8(5) . . ? C6 C11 C14 108.6(5) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 C16 120.2(5) . . ? N1 C15 C18 122.6(5) . . ? C16 C15 C18 117.1(5) . . ? C17 C16 C15 128.9(5) . . ? C17 C16 H16 115.5 . . ? C15 C16 H16 115.5 . . ? N2 C17 C16 122.7(5) . . ? N2 C17 C19 120.1(5) . . ? C16 C17 C19 117.3(5) . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 121.4(5) . . ? C25 C20 N2 118.8(5) . . ? C21 C20 N2 119.6(5) . . ? C22 C21 C20 117.2(5) . . ? C22 C21 C26 119.3(5) . . ? C20 C21 C26 123.5(5) . . ? C23 C22 C21 122.4(5) . . ? C23 C22 H22 118.8 . . ? C21 C22 H22 118.8 . . ? C22 C23 C24 118.8(5) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C25 C24 C23 121.7(6) . . ? C25 C24 H24 119.2 . . ? C23 C24 H24 119.2 . . ? C24 C25 C20 118.5(5) . . ? C24 C25 C29 119.4(5) . . ? C20 C25 C29 122.1(5) . . ? C21 C26 C28 112.2(5) . . ? C21 C26 C27 111.6(5) . . ? C28 C26 C27 109.0(5) . . ? C21 C26 H26 108.0 . . ? C28 C26 H26 108.0 . . ? C27 C26 H26 108.0 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C31 C29 C25 112.5(6) . . ? C31 C29 C30 111.8(7) . . ? C25 C29 C30 109.4(5) . . ? C31 C29 H29 107.7 . . ? C25 C29 H29 107.7 . . ? C30 C29 H29 107.7 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C33 C32 C34 118.7(10) . 2_566 ? C33 C32 H32 120.7 . . ? C34 C32 H32 120.7 2_566 . ? C32 C33 C34 122.7(8) . . ? C32 C33 H33 118.7 . . ? C34 C33 H33 118.7 . . ? C32 C34 C33 118.6(9) 2_566 . ? C32 C34 H34 120.7 2_566 . ? C33 C34 H34 120.7 . . ? data_7 _database_code_depnum_ccdc_archive 'CCDC 878336' #TrackingRef 'web_deposit_cif_file_0_PierreThuery_1335341178.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48.50 H61.50 Cl N5.50 O Yb' _chemical_formula_weight 946.02 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 41.3998(7) _cell_length_b 13.7026(3) _cell_length_c 18.7083(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.5953(7) _cell_angle_gamma 90.00 _cell_volume 9868.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 150085 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 30.51 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent dark yellow' _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3888 _exptl_absorpt_coefficient_mu 1.987 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.614 _exptl_absorpt_correction_T_max 0.888 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 50 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and seven \w scans with 1\% steps (1332 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 150085 _diffrn_reflns_av_R_equivalents 0.0693 _diffrn_reflns_av_sigmaI/netI 0.0817 _diffrn_reflns_limit_h_min -59 _diffrn_reflns_limit_h_max 59 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 30.51 _reflns_number_total 15063 _reflns_number_gt 10452 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. One tert-butyl group is disordered over two positions which were refined with occupancy parameters constrained to sum to unity. The pyridine solvent molecule has been given an occupancy parameter of 0.5 in order to retain acceptable displacement parameters and to account for its closeness to its image by symmetry. All non-hydrogen atoms were refined with anisotropic displacement parameters, with restraints on bond lengths and/or displacement parameters for some badly behaving atoms, particularly in the disordered group and the solvent molecule. The H atoms bound were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (CH) or 1.5 (CH~3~) times that of the parent atom. Some voids in the lattice likely indicate the presence of other, unresolved solvent molecules. 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^)+(0.0647P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 15063 _refine_ls_number_parameters 577 _refine_ls_number_restraints 246 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1267 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.897 _refine_diff_density_min -2.110 _refine_diff_density_rms 0.145 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 Yb Yb 0.392075(5) 0.656055(12) 0.488124(9) 0.03131(6) Uani 1 1 d . . . Cl1 Cl 0.40632(3) 0.48839(8) 0.43656(7) 0.0445(3) Uani 1 1 d . . . O1 O 0.38540(8) 0.7601(2) 0.56963(16) 0.0386(7) Uani 1 1 d . . . N1 N 0.40116(10) 0.8092(3) 0.45452(19) 0.0359(8) Uani 1 1 d . . . N2 N 0.35483(9) 0.6802(3) 0.3548(2) 0.0407(8) Uani 1 1 d . . . N3 N 0.45623(10) 0.6698(3) 0.5445(2) 0.0400(8) Uani 1 1 d . . . N4 N 0.41192(10) 0.5581(3) 0.6145(2) 0.0427(9) Uani 1 1 d . . . N5 N 0.33921(11) 0.5875(3) 0.4967(2) 0.0507(10) Uani 1 1 d . . . C1 C 0.38874(13) 0.8577(3) 0.5617(2) 0.0395(10) Uani 1 1 d . . . C2 C 0.39823(11) 0.8878(3) 0.4999(2) 0.0376(10) Uani 1 1 d . . . C3 C 0.39886(15) 0.9861(3) 0.4829(3) 0.0557(14) Uani 1 1 d . . . H3 H 0.4044 1.0044 0.4409 0.067 Uiso 1 1 calc R . . C4 C 0.39154(17) 1.0562(3) 0.5260(3) 0.0611(15) Uani 1 1 d . A . C5 C 0.38355(15) 1.0269(4) 0.5882(3) 0.0562(14) Uani 1 1 d . . . H5 H 0.3790 1.0747 0.6185 0.067 Uiso 1 1 calc R . . C6 C 0.38198(14) 0.9290(4) 0.6081(2) 0.0475(12) Uani 1 1 d . . . C7 C 0.3899(2) 1.1653(4) 0.5022(5) 0.094(3) Uani 1 1 d D . . C8A C 0.3545(4) 1.2033(17) 0.4990(13) 0.097(3) Uani 0.350(7) 1 d PDU A 1 H8A H 0.3518 1.2706 0.4836 0.146 Uiso 0.350(7) 1 d PR A 1 H8B H 0.3368 1.1650 0.4619 0.146 Uiso 0.350(7) 1 d PR A 1 H8C H 0.3527 1.1969 0.5484 0.146 Uiso 0.350(7) 1 d PR A 1 C9A C 0.4105(7) 1.2178(15) 0.5788(9) 0.101(3) Uani 0.350(7) 1 d PDU A 1 H9A H 0.4097 1.2866 0.5685 0.151 Uiso 0.350(7) 1 d PR A 1 H9B H 0.3967 1.2035 0.6090 0.151 Uiso 0.350(7) 1 d PR A 1 H9C H 0.4341 1.1985 0.6065 0.151 Uiso 0.350(7) 1 d PR A 1 C10A C 0.3984(8) 1.1944(15) 0.4352(12) 0.090(3) Uani 0.350(7) 1 d PDU A 1 H10A H 0.3953 1.2632 0.4256 0.135 Uiso 0.350(7) 1 d PR A 1 H10B H 0.4214 1.1638 0.4439 0.135 Uiso 0.350(7) 1 d PR A 1 H10C H 0.3851 1.1591 0.3895 0.135 Uiso 0.350(7) 1 d PR A 1 C8B C 0.3628(3) 1.1795(8) 0.4204(6) 0.098(3) Uani 0.650(7) 1 d PDU A 2 H8D H 0.3610 1.2467 0.4048 0.147 Uiso 0.650(7) 1 d PR A 2 H8E H 0.3688 1.1405 0.3845 0.147 Uiso 0.650(7) 1 d PR A 2 H8F H 0.3410 1.1579 0.4218 0.147 Uiso 0.650(7) 1 d PR A 2 C9B C 0.3858(4) 1.2394(6) 0.5579(6) 0.086(2) Uani 0.650(7) 1 d PDU A 2 H9D H 0.3844 1.3030 0.5355 0.129 Uiso 0.650(7) 1 d PR A 2 H9E H 0.3649 1.2264 0.5673 0.129 Uiso 0.650(7) 1 d PR A 2 H9F H 0.4054 1.2369 0.6056 0.129 Uiso 0.650(7) 1 d PR A 2 C10B C 0.4212(3) 1.1924(8) 0.4823(8) 0.095(3) Uani 0.650(7) 1 d PDU A 2 H10D H 0.4195 1.2598 0.4674 0.142 Uiso 0.650(7) 1 d PR A 2 H10E H 0.4427 1.1816 0.5246 0.142 Uiso 0.650(7) 1 d PR A 2 H10F H 0.4205 1.1523 0.4396 0.142 Uiso 0.650(7) 1 d PR A 2 C11 C 0.3730(2) 0.8986(4) 0.6786(3) 0.0698(19) Uani 1 1 d . . . C12 C 0.3675(2) 0.9885(5) 0.7223(3) 0.094(2) Uani 1 1 d U . . H12A H 0.3875 1.0302 0.7358 0.141 Uiso 1 1 calc R . . H12B H 0.3642 0.9677 0.7681 0.141 Uiso 1 1 calc R . . H12C H 0.3473 1.0237 0.6901 0.141 Uiso 1 1 calc R . . C13 C 0.3401(2) 0.8401(5) 0.6542(4) 0.090(3) Uani 1 1 d . . . H13A H 0.3208 0.8812 0.6263 0.134 Uiso 1 1 calc R . . H13B H 0.3369 0.8143 0.6988 0.134 Uiso 1 1 calc R . . H13C H 0.3416 0.7874 0.6218 0.134 Uiso 1 1 calc R . . C14 C 0.4031(2) 0.8403(4) 0.7341(3) 0.093(3) Uani 1 1 d . . . H14A H 0.4072 0.7837 0.7083 0.139 Uiso 1 1 calc R . . H14B H 0.3976 0.8202 0.7773 0.139 Uiso 1 1 calc R . . H14C H 0.4237 0.8801 0.7515 0.139 Uiso 1 1 calc R . . C15 C 0.41752(12) 0.8103(3) 0.4048(3) 0.0413(10) Uani 1 1 d . . . C16 C 0.40620(12) 0.7471(3) 0.3418(2) 0.0430(11) Uani 1 1 d . . . H16 H 0.4219 0.7306 0.3189 0.052 Uiso 1 1 calc R . . C17 C 0.37212(13) 0.7058(4) 0.3100(2) 0.0470(12) Uani 1 1 d . . . C18 C 0.44811(15) 0.8741(4) 0.4144(3) 0.0606(15) Uani 1 1 d . . . H18A H 0.4398 0.9322 0.3845 0.091 Uiso 1 1 d R . . H18B H 0.4644 0.8416 0.3970 0.091 Uiso 1 1 d R . . H18C H 0.4594 0.8913 0.4676 0.091 Uiso 1 1 d R . . C19 C 0.35641(15) 0.7016(5) 0.2234(3) 0.0637(16) Uani 1 1 d . . . H19A H 0.3315 0.7042 0.2068 0.095 Uiso 1 1 calc R . . H19B H 0.3631 0.6418 0.2060 0.095 Uiso 1 1 calc R . . H19C H 0.3645 0.7560 0.2023 0.095 Uiso 1 1 calc R . . C20 C 0.31782(13) 0.6656(4) 0.3224(3) 0.0554(14) Uani 1 1 d . . . C21 C 0.29697(14) 0.7425(5) 0.3323(3) 0.0612(15) Uani 1 1 d . . . C22 C 0.26103(16) 0.7290(6) 0.3046(4) 0.079(2) Uani 1 1 d . . . H22 H 0.2469 0.7789 0.3100 0.095 Uiso 1 1 calc R . . C23 C 0.24647(17) 0.6450(6) 0.2703(4) 0.100(3) Uani 1 1 d . . . H23 H 0.2224 0.6380 0.2521 0.120 Uiso 1 1 calc R . . C24 C 0.26711(16) 0.5678(6) 0.2616(4) 0.099(2) Uani 1 1 d U . . H24 H 0.2566 0.5100 0.2384 0.119 Uiso 1 1 calc R . . C25 C 0.30306(14) 0.5771(6) 0.2872(4) 0.084(2) Uani 1 1 d . . . C26 C 0.31310(16) 0.8389(4) 0.3740(3) 0.0619(15) Uani 1 1 d . . . H26 H 0.3354 0.8212 0.4138 0.074 Uiso 1 1 calc R . . C27 C 0.3212(2) 0.9049(6) 0.3199(4) 0.099(3) Uani 1 1 d . . . H27A H 0.3022 0.9050 0.2713 0.149 Uiso 1 1 calc R . . H27B H 0.3418 0.8825 0.3130 0.149 Uiso 1 1 calc R . . H27C H 0.3249 0.9699 0.3406 0.149 Uiso 1 1 calc R . . C28 C 0.29286(16) 0.8928(5) 0.4145(3) 0.0716(17) Uani 1 1 d . . . H28A H 0.3073 0.9424 0.4471 0.107 Uiso 1 1 calc R . . H28B H 0.2857 0.8477 0.4451 0.107 Uiso 1 1 calc R . . H28C H 0.2727 0.9226 0.3770 0.107 Uiso 1 1 calc R . . C29 C 0.32373(17) 0.4951(6) 0.2714(4) 0.089(2) Uani 1 1 d U . . H29 H 0.3482 0.5146 0.2906 0.107 Uiso 1 1 calc R . . C30 C 0.3120(2) 0.4759(6) 0.1832(4) 0.110(3) Uani 1 1 d U . . H30A H 0.3250 0.4221 0.1745 0.165 Uiso 1 1 calc R . . H30B H 0.3162 0.5332 0.1584 0.165 Uiso 1 1 calc R . . H30C H 0.2877 0.4607 0.1626 0.165 Uiso 1 1 calc R . . C31 C 0.3208(2) 0.4062(7) 0.3112(5) 0.117(3) Uani 1 1 d U . . H31A H 0.2974 0.3995 0.3092 0.175 Uiso 1 1 calc R . . H31B H 0.3364 0.4096 0.3639 0.175 Uiso 1 1 calc R . . H31C H 0.3266 0.3509 0.2869 0.175 Uiso 1 1 calc R . . C32 C 0.47033(14) 0.7236(4) 0.6083(3) 0.0548(13) Uani 1 1 d . . . H32 H 0.4557 0.7530 0.6295 0.066 Uiso 1 1 calc R . . C33 C 0.50524(16) 0.7372(5) 0.6434(3) 0.0759(19) Uani 1 1 d . . . H33 H 0.5140 0.7750 0.6877 0.091 Uiso 1 1 calc R . . C34 C 0.52759(14) 0.6944(5) 0.6130(3) 0.0649(15) Uani 1 1 d . . . H34 H 0.5515 0.7017 0.6366 0.078 Uiso 1 1 calc R . . C35 C 0.51345(14) 0.6410(4) 0.5469(3) 0.0565(14) Uani 1 1 d . . . H35 H 0.5277 0.6124 0.5242 0.068 Uiso 1 1 calc R . . C36 C 0.47792(12) 0.6300(4) 0.5145(3) 0.0469(11) Uani 1 1 d . . . H36 H 0.4686 0.5933 0.4698 0.056 Uiso 1 1 calc R . . C37 C 0.43592(14) 0.4866(4) 0.6327(3) 0.0558(13) Uani 1 1 d . . . H37 H 0.4446 0.4675 0.5955 0.067 Uiso 1 1 calc R . . C38 C 0.44840(16) 0.4400(4) 0.7023(3) 0.0717(17) Uani 1 1 d . . . H38 H 0.4648 0.3905 0.7120 0.086 Uiso 1 1 calc R . . C39 C 0.43569(16) 0.4691(5) 0.7576(3) 0.0696(17) Uani 1 1 d . . . H39 H 0.4438 0.4401 0.8059 0.084 Uiso 1 1 calc R . . C40 C 0.41166(16) 0.5393(4) 0.7412(3) 0.0597(14) Uani 1 1 d . . . H40 H 0.4029 0.5592 0.7780 0.072 Uiso 1 1 calc R . . C41 C 0.39989(13) 0.5823(4) 0.6695(3) 0.0485(12) Uani 1 1 d . . . H41 H 0.3828 0.6302 0.6589 0.058 Uiso 1 1 calc R . . C42 C 0.31298(16) 0.6463(4) 0.4938(4) 0.0679(18) Uani 1 1 d . . . H42 H 0.3166 0.7134 0.4951 0.082 Uiso 1 1 calc R . . C43 C 0.28091(18) 0.6127(7) 0.4889(5) 0.107(3) Uani 1 1 d . . . H43 H 0.2636 0.6568 0.4874 0.128 Uiso 1 1 calc R . . C44 C 0.2746(2) 0.5176(7) 0.4865(6) 0.122(3) Uani 1 1 d . . . H44 H 0.2529 0.4942 0.4817 0.146 Uiso 1 1 calc R . . C45 C 0.3012(2) 0.4541(6) 0.4911(5) 0.104(2) Uani 1 1 d U . . H45 H 0.2978 0.3870 0.4913 0.125 Uiso 1 1 calc R . . C46 C 0.33286(16) 0.4921(4) 0.4955(4) 0.0701(17) Uani 1 1 d . . . H46 H 0.3505 0.4489 0.4977 0.084 Uiso 1 1 calc R . . N6 N 0.2556(5) 0.2664(14) 0.5821(8) 0.128(4) Uani 0.50 1 d PDU B -3 C47 C 0.2709(5) 0.2157(15) 0.5398(11) 0.114(4) Uani 0.50 1 d PDU B -3 H47 H 0.2918 0.1800 0.5672 0.137 Uiso 0.50 1 d PR B -3 C48 C 0.2564(5) 0.2185(14) 0.4628(10) 0.123(4) Uani 0.50 1 d PDU B -3 H48 H 0.2663 0.1765 0.4352 0.148 Uiso 0.50 1 d PR B -3 C49 C 0.2289(5) 0.2781(16) 0.4260(9) 0.128(4) Uani 0.50 1 d PDU B -3 H49 H 0.2203 0.2800 0.3709 0.153 Uiso 0.50 1 d PR B -3 C50 C 0.2143(4) 0.3320(11) 0.4679(12) 0.128(4) Uani 0.50 1 d PDU B -3 H50 H 0.1949 0.3729 0.4403 0.153 Uiso 0.50 1 d PR B -3 C51 C 0.2280(5) 0.3263(13) 0.5450(12) 0.130(4) Uani 0.50 1 d PDU B -3 H51 H 0.2178 0.3675 0.5727 0.156 Uiso 0.50 1 d PR B -3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Yb 0.03523(10) 0.02675(9) 0.03556(10) 0.00218(7) 0.01726(7) 0.00416(8) Cl1 0.0416(6) 0.0338(5) 0.0592(7) -0.0124(5) 0.0200(5) 0.0017(5) O1 0.056(2) 0.0268(15) 0.0413(15) 0.0046(12) 0.0280(15) 0.0101(14) N1 0.048(2) 0.0299(17) 0.0388(18) 0.0062(15) 0.0261(17) 0.0042(16) N2 0.0330(19) 0.050(2) 0.0379(18) -0.0003(16) 0.0112(16) 0.0084(17) N3 0.040(2) 0.039(2) 0.0417(19) 0.0008(16) 0.0149(16) -0.0015(16) N4 0.045(2) 0.040(2) 0.048(2) 0.0132(17) 0.0229(18) 0.0046(18) N5 0.048(2) 0.047(2) 0.066(3) 0.007(2) 0.032(2) 0.000(2) C1 0.053(3) 0.033(2) 0.037(2) 0.0017(17) 0.022(2) 0.010(2) C2 0.045(3) 0.032(2) 0.040(2) 0.0026(17) 0.020(2) 0.0001(19) C3 0.089(4) 0.026(2) 0.072(3) 0.007(2) 0.052(3) 0.008(2) C4 0.101(5) 0.026(2) 0.071(3) 0.003(2) 0.050(3) 0.010(3) C5 0.086(4) 0.035(3) 0.054(3) -0.005(2) 0.033(3) 0.017(3) C6 0.068(3) 0.042(3) 0.036(2) -0.0008(19) 0.023(2) 0.014(2) C7 0.145(9) 0.029(3) 0.128(7) -0.013(3) 0.074(7) -0.002(4) C8A 0.125(5) 0.072(4) 0.106(5) 0.006(4) 0.054(4) 0.005(4) C9A 0.144(7) 0.055(5) 0.113(6) 0.008(5) 0.058(6) 0.005(5) C10A 0.137(7) 0.047(5) 0.104(6) 0.008(5) 0.066(6) 0.007(5) C8B 0.154(6) 0.052(4) 0.103(5) 0.013(4) 0.065(5) 0.015(5) C9B 0.134(6) 0.039(4) 0.106(5) -0.002(4) 0.070(5) 0.016(4) C10B 0.143(6) 0.048(4) 0.116(5) 0.013(4) 0.073(5) 0.001(5) C11 0.123(6) 0.052(3) 0.052(3) 0.008(3) 0.052(4) 0.037(4) C12 0.163(6) 0.072(4) 0.065(3) 0.006(3) 0.062(4) 0.054(4) C13 0.123(7) 0.085(5) 0.102(5) 0.031(4) 0.090(5) 0.032(4) C14 0.164(8) 0.079(5) 0.039(3) 0.014(3) 0.042(4) 0.052(5) C15 0.050(3) 0.035(2) 0.048(2) 0.009(2) 0.028(2) 0.006(2) C16 0.047(3) 0.053(3) 0.038(2) 0.006(2) 0.027(2) 0.011(2) C17 0.055(3) 0.057(3) 0.030(2) 0.006(2) 0.016(2) 0.020(2) C18 0.072(4) 0.043(3) 0.088(4) 0.004(3) 0.054(3) -0.004(3) C19 0.060(3) 0.085(4) 0.038(3) -0.001(3) 0.009(2) 0.021(3) C20 0.035(2) 0.079(4) 0.048(3) -0.012(3) 0.010(2) 0.012(3) C21 0.043(3) 0.079(4) 0.059(3) 0.002(3) 0.016(3) 0.018(3) C22 0.045(3) 0.110(6) 0.075(4) -0.007(4) 0.013(3) 0.010(4) C23 0.039(3) 0.168(9) 0.082(5) -0.049(5) 0.011(3) 0.005(4) C24 0.048(3) 0.127(6) 0.112(5) -0.059(4) 0.017(3) -0.003(4) C25 0.032(3) 0.119(6) 0.085(4) -0.062(4) 0.005(3) 0.002(3) C26 0.055(3) 0.074(4) 0.061(3) 0.012(3) 0.026(3) 0.013(3) C27 0.119(6) 0.097(6) 0.110(6) 0.037(5) 0.076(5) 0.046(5) C28 0.075(4) 0.071(4) 0.069(4) 0.013(3) 0.027(3) 0.034(3) C29 0.052(3) 0.100(5) 0.103(5) -0.061(4) 0.014(3) -0.003(4) C30 0.088(4) 0.123(5) 0.116(4) -0.059(4) 0.035(3) -0.009(3) C31 0.071(5) 0.110(6) 0.146(6) -0.062(5) 0.013(4) 0.008(4) C32 0.053(3) 0.057(3) 0.055(3) -0.018(3) 0.020(3) -0.008(3) C33 0.056(4) 0.101(5) 0.058(3) -0.028(3) 0.006(3) -0.026(4) C34 0.039(3) 0.086(4) 0.063(3) -0.003(3) 0.011(3) -0.007(3) C35 0.044(3) 0.048(3) 0.083(4) -0.009(3) 0.030(3) 0.001(2) C36 0.039(3) 0.041(2) 0.064(3) -0.006(2) 0.023(2) -0.001(2) C37 0.057(3) 0.050(3) 0.062(3) 0.021(2) 0.023(3) 0.017(3) C38 0.069(4) 0.060(4) 0.070(4) 0.034(3) 0.007(3) 0.013(3) C39 0.076(4) 0.072(4) 0.051(3) 0.030(3) 0.012(3) -0.001(3) C40 0.078(4) 0.060(3) 0.045(3) 0.013(2) 0.027(3) -0.010(3) C41 0.056(3) 0.046(3) 0.053(3) 0.012(2) 0.031(2) 0.005(2) C42 0.057(3) 0.055(4) 0.110(5) 0.025(3) 0.051(4) 0.012(3) C43 0.064(4) 0.104(6) 0.181(8) 0.059(6) 0.079(5) 0.027(4) C44 0.070(5) 0.109(7) 0.208(10) 0.024(7) 0.077(6) -0.002(5) C45 0.085(5) 0.064(4) 0.171(7) -0.002(4) 0.055(5) -0.025(4) C46 0.064(4) 0.044(3) 0.117(5) -0.002(3) 0.050(4) -0.013(3) N6 0.110(7) 0.109(7) 0.154(7) 0.003(6) 0.034(6) -0.042(5) C47 0.107(5) 0.107(6) 0.130(5) 0.001(4) 0.046(4) -0.035(4) C48 0.108(7) 0.107(7) 0.148(7) 0.005(6) 0.040(6) -0.054(6) C49 0.110(7) 0.108(7) 0.153(7) 0.006(6) 0.033(6) -0.055(6) C50 0.111(7) 0.105(7) 0.152(7) 0.009(6) 0.032(6) -0.060(6) C51 0.112(7) 0.109(7) 0.153(7) 0.002(6) 0.030(6) -0.049(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Yb O1 2.178(3) . ? Yb N1 2.262(4) . ? Yb N2 2.424(4) . ? Yb N5 2.441(4) . ? Yb N3 2.478(4) . ? Yb N4 2.575(3) . ? Yb Cl1 2.6410(10) . ? Yb C15 3.036(4) . ? Yb C1 3.112(4) . ? Yb C2 3.187(5) . ? Yb C17 3.198(4) . ? O1 C1 1.358(5) . ? N1 C15 1.337(5) . ? N1 C2 1.404(5) . ? N2 C17 1.334(6) . ? N2 C20 1.439(6) . ? N3 C36 1.338(6) . ? N3 C32 1.340(6) . ? N4 C41 1.340(5) . ? N4 C37 1.347(6) . ? N5 C46 1.332(6) . ? N5 C42 1.338(6) . ? C1 C6 1.402(6) . ? C1 C2 1.413(5) . ? C2 C3 1.386(6) . ? C3 C4 1.359(7) . ? C3 H3 0.9300 . ? C4 C5 1.383(7) . ? C4 C7 1.554(7) . ? C5 C6 1.399(7) . ? C5 H5 0.9300 . ? C6 C11 1.554(6) . ? C7 C10A 1.476(9) . ? C7 C9B 1.509(8) . ? C7 C10B 1.522(8) . ? C7 C8A 1.535(10) . ? C7 C8B 1.540(8) . ? C7 C9A 1.549(10) . ? C8A H8A 0.9600 . ? C8A H8B 0.9596 . ? C8A H8C 0.9604 . ? C9A H9A 0.9598 . ? C9A H9B 0.9598 . ? C9A H9C 0.9607 . ? C10A H10A 0.9601 . ? C10A H10B 0.9950 . ? C10A H10C 0.9600 . ? C8B H8D 0.9602 . ? C8B H8E 0.9605 . ? C8B H8F 0.9601 . ? C9B H9D 0.9600 . ? C9B H9E 0.9601 . ? C9B H9F 0.9600 . ? C10B H10D 0.9598 . ? C10B H10E 0.9600 . ? C10B H10F 0.9602 . ? C11 C13 1.498(10) . ? C11 C14 1.524(9) . ? C11 C12 1.541(7) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.399(6) . ? C15 C18 1.494(7) . ? C16 C17 1.431(7) . ? C16 H16 0.9300 . ? C17 C19 1.508(6) . ? C18 H18A 0.9601 . ? C18 H18B 0.9603 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C25 1.408(8) . ? C20 C21 1.416(7) . ? C21 C22 1.396(8) . ? C21 C26 1.555(8) . ? C22 C23 1.347(9) . ? C22 H22 0.9300 . ? C23 C24 1.406(10) . ? C23 H23 0.9300 . ? C24 C25 1.391(8) . ? C24 H24 0.9300 . ? C25 C29 1.507(8) . ? C26 C27 1.485(8) . ? C26 C28 1.513(7) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C31 1.457(11) . ? C29 C30 1.561(9) . ? C29 H29 0.9800 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 C33 1.362(7) . ? C32 H32 0.9300 . ? C33 C34 1.383(8) . ? C33 H33 0.9300 . ? C34 C35 1.368(8) . ? C34 H34 0.9300 . ? C35 C36 1.377(7) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 C38 1.370(7) . ? C37 H37 0.9300 . ? C38 C39 1.380(8) . ? C38 H38 0.9300 . ? C39 C40 1.336(8) . ? C39 H39 0.9300 . ? C40 C41 1.379(6) . ? C40 H40 0.9300 . ? C41 H41 0.9300 . ? C42 C43 1.376(8) . ? C42 H42 0.9300 . ? C43 C44 1.327(11) . ? C43 H43 0.9300 . ? C44 C45 1.378(10) . ? C44 H44 0.9300 . ? C45 C46 1.386(9) . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? N6 C47 1.370(8) . ? N6 C51 1.372(8) . ? C47 C48 1.342(8) . ? C47 H47 0.9599 . ? C48 C49 1.364(8) . ? C48 H48 0.9598 . ? C49 C50 1.367(8) . ? C49 H49 0.9600 . ? C50 C51 1.345(8) . ? C50 H50 0.9605 . ? C51 H51 0.9601 . ? 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 Yb N1 70.38(10) . . ? O1 Yb N2 115.76(12) . . ? N1 Yb N2 72.26(13) . . ? O1 Yb N5 81.85(13) . . ? N1 Yb N5 128.35(13) . . ? N2 Yb N5 82.76(13) . . ? O1 Yb N3 92.54(12) . . ? N1 Yb N3 77.64(13) . . ? N2 Yb N3 127.15(12) . . ? N5 Yb N3 147.98(13) . . ? O1 Yb N4 77.19(11) . . ? N1 Yb N4 135.16(13) . . ? N2 Yb N4 151.95(13) . . ? N5 Yb N4 74.33(13) . . ? N3 Yb N4 73.68(12) . . ? O1 Yb Cl1 158.12(8) . . ? N1 Yb Cl1 128.56(9) . . ? N2 Yb Cl1 83.44(9) . . ? N5 Yb Cl1 90.87(10) . . ? N3 Yb Cl1 82.72(9) . . ? N4 Yb Cl1 80.98(9) . . ? C1 O1 Yb 121.6(2) . . ? C15 N1 C2 126.2(4) . . ? C15 N1 Yb 112.5(3) . . ? C2 N1 Yb 118.9(2) . . ? C17 N2 C20 120.4(4) . . ? C17 N2 Yb 113.4(3) . . ? C20 N2 Yb 126.1(3) . . ? C36 N3 C32 117.3(4) . . ? C36 N3 Yb 124.8(3) . . ? C32 N3 Yb 117.9(3) . . ? C41 N4 C37 115.7(4) . . ? C41 N4 Yb 119.6(3) . . ? C37 N4 Yb 124.6(3) . . ? C46 N5 C42 116.0(5) . . ? C46 N5 Yb 123.6(4) . . ? C42 N5 Yb 119.9(3) . . ? O1 C1 C6 124.5(4) . . ? O1 C1 C2 116.6(4) . . ? C6 C1 C2 118.8(4) . . ? C3 C2 N1 126.4(4) . . ? C3 C2 C1 120.4(4) . . ? N1 C2 C1 112.5(4) . . ? C4 C3 C2 121.6(4) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 118.0(5) . . ? C3 C4 C7 120.4(5) . . ? C5 C4 C7 121.5(5) . . ? C4 C5 C6 123.5(4) . . ? C4 C5 H5 118.3 . . ? C6 C5 H5 118.3 . . ? C5 C6 C1 117.6(4) . . ? C5 C6 C11 122.1(4) . . ? C1 C6 C11 120.3(4) . . ? C9B C7 C10B 109.1(8) . . ? C10A C7 C8A 113.5(14) . . ? C9B C7 C8B 112.0(8) . . ? C10B C7 C8B 95.8(8) . . ? C10A C7 C9A 116.0(15) . . ? C8A C7 C9A 94.0(13) . . ? C10A C7 C4 120.3(10) . . ? C9B C7 C4 117.0(6) . . ? C10B C7 C4 110.7(7) . . ? C8A C7 C4 106.1(10) . . ? C8B C7 C4 110.2(6) . . ? C9A C7 C4 103.3(10) . . ? C7 C8A H8A 110.2 . . ? C7 C8A H8B 108.0 . . ? H8A C8A H8B 109.5 . . ? C7 C8A H8C 110.2 . . ? H8A C8A H8C 109.5 . . ? H8B C8A H8C 109.5 . . ? C7 C9A H9A 107.8 . . ? C7 C9A H9B 102.0 . . ? H9A C9A H9B 109.5 . . ? C7 C9A H9C 118.3 . . ? H9A C9A H9C 109.4 . . ? H9B C9A H9C 109.4 . . ? C7 C10A H10A 111.4 . . ? C7 C10A H10B 105.1 . . ? H10A C10A H10B 120.1 . . ? C7 C10A H10C 112.4 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 97.7 . . ? C7 C8B H8B 82.7 . . ? C7 C8B H10C 92.2 . . ? H8B C8B H10C 159.9 . . ? C7 C8B H8E 110.1 . . ? H8D C8B H8E 109.5 . . ? C7 C8B H8F 106.4 . . ? H8D C8B H8F 109.4 . . ? H8E C8B H8F 109.5 . . ? C7 C9B H9D 108.3 . . ? C7 C9B H9E 109.9 . . ? H9D C9B H9E 109.5 . . ? C7 C9B H9F 110.3 . . ? H9D C9B H9F 109.5 . . ? H9E C9B H9F 109.5 . . ? C7 C10B H10D 109.0 . . ? C7 C10B H10E 112.1 . . ? H10D C10B H10E 109.5 . . ? C7 C10B H10F 107.3 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C13 C11 C14 110.6(6) . . ? C13 C11 C12 107.1(6) . . ? C14 C11 C12 107.7(5) . . ? C13 C11 C6 111.0(5) . . ? C14 C11 C6 109.0(5) . . ? C12 C11 C6 111.4(5) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 C16 118.8(4) . . ? N1 C15 C18 123.1(4) . . ? C16 C15 C18 118.1(4) . . ? C15 C16 C17 124.7(4) . . ? C15 C16 H16 117.7 . . ? C17 C16 H16 117.7 . . ? N2 C17 C16 121.2(4) . . ? N2 C17 C19 123.1(5) . . ? C16 C17 C19 115.5(4) . . ? C15 C18 H18A 108.0 . . ? C15 C18 H18B 110.9 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C25 C20 C21 121.4(5) . . ? C25 C20 N2 121.9(4) . . ? C21 C20 N2 116.6(5) . . ? C22 C21 C20 118.1(6) . . ? C22 C21 C26 120.0(5) . . ? C20 C21 C26 121.8(5) . . ? C23 C22 C21 121.2(6) . . ? C23 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C22 C23 C24 120.9(6) . . ? C22 C23 H23 119.6 . . ? C24 C23 H23 119.6 . . ? C25 C24 C23 120.6(7) . . ? C25 C24 H24 119.7 . . ? C23 C24 H24 119.7 . . ? C24 C25 C20 117.7(6) . . ? C24 C25 C29 118.5(6) . . ? C20 C25 C29 123.7(5) . . ? C27 C26 C28 110.5(5) . . ? C27 C26 C21 109.8(5) . . ? C28 C26 C21 116.9(5) . . ? C27 C26 H26 106.4 . . ? C28 C26 H26 106.4 . . ? C21 C26 H26 106.4 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C31 C29 C25 111.2(7) . . ? C31 C29 C30 110.4(6) . . ? C25 C29 C30 110.8(6) . . ? C31 C29 H29 108.1 . . ? C25 C29 H29 108.1 . . ? C30 C29 H29 108.1 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N3 C32 C33 122.8(5) . . ? N3 C32 H32 118.6 . . ? C33 C32 H32 118.6 . . ? C32 C33 C34 119.7(5) . . ? C32 C33 H33 120.1 . . ? C34 C33 H33 120.1 . . ? C35 C34 C33 118.0(5) . . ? C35 C34 H34 121.0 . . ? C33 C34 H34 121.0 . . ? C34 C35 C36 119.2(5) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 120.4 . . ? N3 C36 C35 123.0(5) . . ? N3 C36 H36 118.5 . . ? C35 C36 H36 118.5 . . ? N4 C37 C38 124.4(5) . . ? N4 C37 H37 117.8 . . ? C38 C37 H37 117.8 . . ? C37 C38 C39 117.6(5) . . ? C37 C38 H38 121.2 . . ? C39 C38 H38 121.2 . . ? C40 C39 C38 119.6(5) . . ? C40 C39 H39 120.2 . . ? C38 C39 H39 120.2 . . ? C39 C40 C41 119.8(5) . . ? C39 C40 H40 120.1 . . ? C41 C40 H40 120.1 . . ? N4 C41 C40 123.0(5) . . ? N4 C41 H41 118.5 . . ? C40 C41 H41 118.5 . . ? N5 C42 C43 123.4(6) . . ? N5 C42 H42 118.3 . . ? C43 C42 H42 118.3 . . ? C44 C43 C42 120.2(7) . . ? C44 C43 H43 119.9 . . ? C42 C43 H43 119.9 . . ? C43 C44 C45 118.5(7) . . ? C43 C44 H44 120.7 . . ? C45 C44 H44 120.7 . . ? C44 C45 C46 118.8(7) . . ? C44 C45 H45 120.6 . . ? C46 C45 H45 120.6 . . ? N5 C46 C45 123.1(6) . . ? N5 C46 H46 118.4 . . ? C45 C46 H46 118.4 . . ? C47 N6 C51 119.2(7) . . ? C48 C47 N6 119.1(8) . . ? C48 C47 H47 123.2 . . ? N6 C47 H47 117.7 . . ? C47 C48 C49 121.3(8) . . ? C47 C48 H48 116.7 . . ? C49 C48 H48 122.0 . . ? C48 C49 C50 119.8(7) . . ? C48 C49 H49 117.8 . . ? C50 C49 H49 122.4 . . ? C51 C50 C49 118.9(7) . . ? C51 C50 H50 123.2 . . ? C49 C50 H50 117.9 . . ? C50 C51 N6 121.3(8) . . ? C50 C51 H51 116.8 . . ? N6 C51 H51 121.9 . . ? data_8 _database_code_depnum_ccdc_archive 'CCDC 878337' #TrackingRef 'web_deposit_cif_file_0_PierreThuery_1335341178.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C82 H120 Cl5 Li N4 O6 Th2' _chemical_formula_weight 1906.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Th Th -7.2400 8.8979 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.0701(3) _cell_length_b 17.5574(6) _cell_length_c 20.6952(8) _cell_angle_alpha 107.545(2) _cell_angle_beta 100.357(2) _cell_angle_gamma 97.811(3) _cell_volume 4361.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 239700 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 30.51 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.451 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1912 _exptl_absorpt_coefficient_mu 3.608 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.379 _exptl_absorpt_correction_T_max 0.626 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and eleven \w scans with 2\% steps (716 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 239700 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_sigmaI/netI 0.0628 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 30.51 _reflns_number_total 26603 _reflns_number_gt 19958 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (CH, CH~2~) or 1.5 (CH~3~) times that of the parent atom. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0232P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 26603 _refine_ls_number_parameters 929 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0659 _refine_ls_wR_factor_gt 0.0621 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.745 _refine_diff_density_min -1.325 _refine_diff_density_rms 0.113 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 Th1 Th 0.593448(7) 0.287133(5) 0.771368(5) 0.02206(3) Uani 1 1 d . . . Th2 Th 0.655843(7) 0.071274(5) 0.806064(5) 0.02107(3) Uani 1 1 d . . . Li Li 0.5308(4) 0.2594(3) 0.0251(3) 0.0419(13) Uani 1 1 d . . . Cl1 Cl 0.53118(5) 0.11564(4) 0.70015(3) 0.02624(14) Uani 1 1 d . . . Cl2 Cl 0.57332(5) 0.21142(4) 0.87820(4) 0.02952(14) Uani 1 1 d . . . Cl3 Cl 0.78158(5) 0.22194(4) 0.80320(4) 0.02702(14) Uani 1 1 d . . . Cl4 Cl 0.59422(6) 0.42004(4) 0.87740(4) 0.03277(15) Uani 1 1 d . . . Cl5 Cl 0.69547(5) 0.06232(4) 0.93538(4) 0.03074(15) Uani 1 1 d . . . O1 O 0.42045(14) 0.27980(11) 0.74773(9) 0.0261(4) Uani 1 1 d . . . O2 O 0.49821(13) -0.00772(10) 0.78970(9) 0.0252(4) Uani 1 1 d . . . O3 O 0.48005(16) 0.35858(12) 0.02854(13) 0.0464(6) Uani 1 1 d . . . O4 O 0.67179(16) 0.33385(12) 0.06526(11) 0.0386(5) Uani 1 1 d . . . O5 O 0.40048(16) 0.17443(12) -0.01559(11) 0.0400(5) Uani 1 1 d . . . O6 O 0.54067(17) 0.21516(13) 0.10418(12) 0.0440(5) Uani 1 1 d . . . N1 N 0.52299(16) 0.28529(13) 0.65611(11) 0.0233(5) Uani 1 1 d . . . N2 N 0.71661(17) 0.38706(13) 0.74406(11) 0.0238(5) Uani 1 1 d . . . N3 N 0.62380(15) -0.05462(12) 0.71243(11) 0.0225(5) Uani 1 1 d . . . N4 N 0.83042(16) 0.02723(12) 0.80613(11) 0.0230(5) Uani 1 1 d . . . C1 C 0.3581(2) 0.27548(15) 0.68642(14) 0.0238(5) Uani 1 1 d . . . C2 C 0.41112(19) 0.27589(15) 0.63273(14) 0.0234(5) Uani 1 1 d . . . C3 C 0.3568(2) 0.27398(15) 0.56850(14) 0.0257(6) Uani 1 1 d . . . H3 H 0.3931 0.2752 0.5340 0.031 Uiso 1 1 calc R . . C4 C 0.2472(2) 0.27015(16) 0.55516(15) 0.0273(6) Uani 1 1 d . . . C5 C 0.1960(2) 0.26815(16) 0.60844(15) 0.0285(6) Uani 1 1 d . . . H5 H 0.1229 0.2650 0.5995 0.034 Uiso 1 1 calc R . . C6 C 0.2485(2) 0.27065(16) 0.67468(15) 0.0271(6) Uani 1 1 d . . . C7 C 0.1885(2) 0.27056(17) 0.48375(15) 0.0309(6) Uani 1 1 d . . . C8 C 0.0677(2) 0.2581(2) 0.47494(17) 0.0389(7) Uani 1 1 d . . . H8A H 0.0352 0.2601 0.4302 0.058 Uiso 1 1 calc R . . H8B H 0.0511 0.3005 0.5109 0.058 Uiso 1 1 calc R . . H8C H 0.0411 0.2060 0.4782 0.058 Uiso 1 1 calc R . . C9 C 0.2111(2) 0.20214(19) 0.42497(16) 0.0396(7) Uani 1 1 d . . . H9A H 0.2854 0.2122 0.4256 0.059 Uiso 1 1 calc R . . H9B H 0.1705 0.2006 0.3809 0.059 Uiso 1 1 calc R . . H9C H 0.1915 0.1508 0.4316 0.059 Uiso 1 1 calc R . . C10 C 0.2275(2) 0.35286(19) 0.47528(17) 0.0397(7) Uani 1 1 d . . . H10A H 0.3026 0.3607 0.4783 0.060 Uiso 1 1 calc R . . H10B H 0.2131 0.3961 0.5116 0.060 Uiso 1 1 calc R . . H10C H 0.1913 0.3532 0.4307 0.060 Uiso 1 1 calc R . . C11 C 0.1910(2) 0.26601(18) 0.73223(15) 0.0312(6) Uani 1 1 d . . . C12 C 0.0723(2) 0.2639(2) 0.71050(17) 0.0431(8) Uani 1 1 d . . . H12A H 0.0623 0.3125 0.7002 0.065 Uiso 1 1 calc R . . H12B H 0.0395 0.2608 0.7478 0.065 Uiso 1 1 calc R . . H12C H 0.0405 0.2171 0.6698 0.065 Uiso 1 1 calc R . . C13 C 0.2376(2) 0.3411(2) 0.79866(17) 0.0428(8) Uani 1 1 d . . . H13A H 0.3122 0.3437 0.8142 0.064 Uiso 1 1 calc R . . H13B H 0.2023 0.3365 0.8346 0.064 Uiso 1 1 calc R . . H13C H 0.2274 0.3898 0.7885 0.064 Uiso 1 1 calc R . . C14 C 0.2055(2) 0.18779(19) 0.74817(17) 0.0381(7) Uani 1 1 d . . . H14A H 0.1748 0.1413 0.7070 0.057 Uiso 1 1 calc R . . H14B H 0.1708 0.1840 0.7846 0.057 Uiso 1 1 calc R . . H14C H 0.2798 0.1891 0.7629 0.057 Uiso 1 1 calc R . . C15 C 0.5862(2) 0.24584(15) 0.62001(14) 0.0245(6) Uani 1 1 d . . . C16 C 0.6973(2) 0.26916(16) 0.64523(14) 0.0270(6) Uani 1 1 d . . . H16 H 0.7368 0.2300 0.6297 0.032 Uiso 1 1 calc R . . C17 C 0.75514(19) 0.34688(16) 0.69214(14) 0.0245(6) Uani 1 1 d . . . C18 C 0.5432(2) 0.17343(16) 0.55493(14) 0.0278(6) Uani 1 1 d . . . H18A H 0.4743 0.1472 0.5558 0.042 Uiso 1 1 calc R . . H18B H 0.5903 0.1357 0.5523 0.042 Uiso 1 1 calc R . . H18C H 0.5375 0.1910 0.5150 0.042 Uiso 1 1 calc R . . C19 C 0.8562(2) 0.38159(18) 0.67774(16) 0.0359(7) Uani 1 1 d . . . H19A H 0.8445 0.4235 0.6580 0.054 Uiso 1 1 calc R . . H19B H 0.8791 0.3392 0.6455 0.054 Uiso 1 1 calc R . . H19C H 0.9099 0.4044 0.7205 0.054 Uiso 1 1 calc R . . C20 C 0.7584(2) 0.47280(15) 0.78078(14) 0.0263(6) Uani 1 1 d . . . C21 C 0.7055(2) 0.52755(16) 0.75889(15) 0.0318(6) Uani 1 1 d . . . C22 C 0.7381(3) 0.61055(18) 0.79828(18) 0.0431(8) Uani 1 1 d . . . H22 H 0.7040 0.6483 0.7847 0.052 Uiso 1 1 calc R . . C23 C 0.8200(3) 0.63683(19) 0.85676(18) 0.0442(8) Uani 1 1 d . . . H23 H 0.8395 0.6920 0.8831 0.053 Uiso 1 1 calc R . . C24 C 0.8734(2) 0.58222(18) 0.87680(16) 0.0368(7) Uani 1 1 d . . . H24 H 0.9293 0.6011 0.9161 0.044 Uiso 1 1 calc R . . C25 C 0.8448(2) 0.49876(17) 0.83894(15) 0.0298(6) Uani 1 1 d . . . C26 C 0.6116(2) 0.49937(17) 0.69514(16) 0.0369(7) Uani 1 1 d . . . H26 H 0.6123 0.4430 0.6685 0.044 Uiso 1 1 calc R . . C27 C 0.5073(3) 0.4988(2) 0.71797(18) 0.0452(8) Uani 1 1 d . . . H27A H 0.5033 0.4653 0.7469 0.068 Uiso 1 1 calc R . . H27B H 0.4491 0.4774 0.6776 0.068 Uiso 1 1 calc R . . H27C H 0.5037 0.5535 0.7438 0.068 Uiso 1 1 calc R . . C28 C 0.6220(3) 0.5499(2) 0.64711(18) 0.0509(9) Uani 1 1 d . . . H28A H 0.6204 0.6056 0.6715 0.076 Uiso 1 1 calc R . . H28B H 0.5642 0.5284 0.6066 0.076 Uiso 1 1 calc R . . H28C H 0.6880 0.5475 0.6331 0.076 Uiso 1 1 calc R . . C29 C 0.9052(2) 0.43961(17) 0.86219(15) 0.0307(6) Uani 1 1 d . . . H29 H 0.8802 0.3858 0.8261 0.037 Uiso 1 1 calc R . . C30 C 0.8825(2) 0.43193(19) 0.92992(16) 0.0377(7) Uani 1 1 d . . . H30A H 0.9217 0.3946 0.9435 0.057 Uiso 1 1 calc R . . H30B H 0.8079 0.4119 0.9231 0.057 Uiso 1 1 calc R . . H30C H 0.9036 0.4844 0.9658 0.057 Uiso 1 1 calc R . . C31 C 1.0246(2) 0.46437(19) 0.86986(17) 0.0392(7) Uani 1 1 d . . . H31A H 1.0513 0.5168 0.9054 0.059 Uiso 1 1 calc R . . H31B H 1.0378 0.4672 0.8264 0.059 Uiso 1 1 calc R . . H31C H 1.0598 0.4247 0.8826 0.059 Uiso 1 1 calc R . . C32 C 0.45643(19) -0.08008(15) 0.73679(14) 0.0229(5) Uani 1 1 d . . . C33 C 0.52400(19) -0.10941(15) 0.69412(14) 0.0235(5) Uani 1 1 d . . . C34 C 0.4943(2) -0.18565(15) 0.64279(14) 0.0252(6) Uani 1 1 d . . . H34 H 0.5415 -0.2050 0.6162 0.030 Uiso 1 1 calc R . . C35 C 0.3942(2) -0.23320(15) 0.63100(14) 0.0250(6) Uani 1 1 d . . . C36 C 0.3260(2) -0.19973(16) 0.67101(15) 0.0290(6) Uani 1 1 d . . . H36 H 0.2577 -0.2301 0.6617 0.035 Uiso 1 1 calc R . . C37 C 0.3525(2) -0.12411(16) 0.72394(15) 0.0265(6) Uani 1 1 d . . . C38 C 0.3572(2) -0.32070(16) 0.57855(15) 0.0285(6) Uani 1 1 d . . . C39 C 0.4403(2) -0.34770(17) 0.53843(16) 0.0352(7) Uani 1 1 d . . . H39A H 0.4527 -0.3134 0.5111 0.053 Uiso 1 1 calc R . . H39B H 0.4153 -0.4033 0.5083 0.053 Uiso 1 1 calc R . . H39C H 0.5053 -0.3434 0.5707 0.053 Uiso 1 1 calc R . . C40 C 0.3333(3) -0.38012(17) 0.61774(17) 0.0402(7) Uani 1 1 d . . . H40A H 0.3961 -0.3765 0.6517 0.060 Uiso 1 1 calc R . . H40B H 0.3114 -0.4348 0.5853 0.060 Uiso 1 1 calc R . . H40C H 0.2775 -0.3663 0.6408 0.060 Uiso 1 1 calc R . . C41 C 0.2555(2) -0.32684(19) 0.52460(17) 0.0421(8) Uani 1 1 d . . . H41A H 0.2005 -0.3123 0.5482 0.063 Uiso 1 1 calc R . . H41B H 0.2329 -0.3817 0.4927 0.063 Uiso 1 1 calc R . . H41C H 0.2699 -0.2904 0.4994 0.063 Uiso 1 1 calc R . . C42 C 0.2723(2) -0.08913(17) 0.76432(16) 0.0333(7) Uani 1 1 d . . . C43 C 0.3117(2) -0.07535(18) 0.84240(16) 0.0376(7) Uani 1 1 d . . . H43A H 0.3180 -0.1266 0.8488 0.056 Uiso 1 1 calc R . . H43B H 0.2619 -0.0520 0.8673 0.056 Uiso 1 1 calc R . . H43C H 0.3797 -0.0389 0.8599 0.056 Uiso 1 1 calc R . . C44 C 0.1631(2) -0.1470(2) 0.73930(19) 0.0509(9) Uani 1 1 d . . . H44A H 0.1371 -0.1582 0.6902 0.076 Uiso 1 1 calc R . . H44B H 0.1143 -0.1218 0.7640 0.076 Uiso 1 1 calc R . . H44C H 0.1695 -0.1970 0.7480 0.076 Uiso 1 1 calc R . . C45 C 0.2561(2) -0.00916(18) 0.75186(17) 0.0380(7) Uani 1 1 d . . . H45A H 0.3235 0.0277 0.7648 0.057 Uiso 1 1 calc R . . H45B H 0.2099 0.0152 0.7795 0.057 Uiso 1 1 calc R . . H45C H 0.2249 -0.0204 0.7034 0.057 Uiso 1 1 calc R . . C46 C 0.66605(19) -0.02797(15) 0.66707(14) 0.0234(5) Uani 1 1 d . . . C47 C 0.76637(19) 0.02496(15) 0.68924(14) 0.0243(6) Uani 1 1 d . . . H47 H 0.7796 0.0588 0.6634 0.029 Uiso 1 1 calc R . . C48 C 0.85006(19) 0.03213(15) 0.74725(14) 0.0243(6) Uani 1 1 d . . . C49 C 0.6078(2) -0.04744(16) 0.59251(14) 0.0264(6) Uani 1 1 d . . . H49A H 0.6254 -0.0957 0.5638 0.040 Uiso 1 1 calc R . . H49B H 0.6283 -0.0026 0.5769 0.040 Uiso 1 1 calc R . . H49C H 0.5327 -0.0564 0.5892 0.040 Uiso 1 1 calc R . . C50 C 0.9603(2) 0.04275(19) 0.73495(16) 0.0352(7) Uani 1 1 d . . . H50A H 1.0111 0.0672 0.7789 0.053 Uiso 1 1 calc R . . H50B H 0.9662 0.0773 0.7071 0.053 Uiso 1 1 calc R . . H50C H 0.9740 -0.0095 0.7111 0.053 Uiso 1 1 calc R . . C51 C 0.91422(19) 0.01320(16) 0.85430(14) 0.0237(5) Uani 1 1 d . . . C52 C 0.9823(2) 0.07779(16) 0.90924(14) 0.0268(6) Uani 1 1 d . . . C53 C 1.0663(2) 0.05920(18) 0.95052(15) 0.0297(6) Uani 1 1 d . . . H53 H 1.1132 0.1012 0.9871 0.036 Uiso 1 1 calc R . . C54 C 1.0810(2) -0.01934(18) 0.93832(15) 0.0323(6) Uani 1 1 d . . . H54 H 1.1375 -0.0301 0.9663 0.039 Uiso 1 1 calc R . . C55 C 1.0117(2) -0.08272(17) 0.88429(15) 0.0293(6) Uani 1 1 d . . . H55 H 1.0221 -0.1358 0.8765 0.035 Uiso 1 1 calc R . . C56 C 0.9267(2) -0.06839(16) 0.84146(14) 0.0249(6) Uani 1 1 d . . . C57 C 0.9691(2) 0.16555(16) 0.92490(15) 0.0309(6) Uani 1 1 d . . . H57 H 0.9033 0.1654 0.8935 0.037 Uiso 1 1 calc R . . C58 C 0.9580(2) 0.20311(18) 0.99895(16) 0.0390(7) Uani 1 1 d . . . H58A H 1.0204 0.2022 1.0311 0.058 Uiso 1 1 calc R . . H58B H 0.8968 0.1724 1.0059 0.058 Uiso 1 1 calc R . . H58C H 0.9499 0.2585 1.0068 0.058 Uiso 1 1 calc R . . C59 C 1.0595(3) 0.2187(2) 0.9112(2) 0.0597(11) Uani 1 1 d . . . H59A H 1.1257 0.2183 0.9400 0.090 Uiso 1 1 calc R . . H59B H 1.0482 0.2736 0.9220 0.090 Uiso 1 1 calc R . . H59C H 1.0617 0.1976 0.8631 0.090 Uiso 1 1 calc R . . C60 C 0.8452(2) -0.13834(16) 0.78484(15) 0.0291(6) Uani 1 1 d . . . H60 H 0.8218 -0.1195 0.7457 0.035 Uiso 1 1 calc R . . C61 C 0.8870(2) -0.21614(16) 0.75701(16) 0.0339(7) Uani 1 1 d . . . H61A H 0.9466 -0.2042 0.7380 0.051 Uiso 1 1 calc R . . H61B H 0.8319 -0.2565 0.7213 0.051 Uiso 1 1 calc R . . H61C H 0.9088 -0.2366 0.7943 0.051 Uiso 1 1 calc R . . C62 C 0.7482(2) -0.15743(17) 0.81429(17) 0.0363(7) Uani 1 1 d . . . H62A H 0.7682 -0.1795 0.8508 0.054 Uiso 1 1 calc R . . H62B H 0.6927 -0.1965 0.7778 0.054 Uiso 1 1 calc R . . H62C H 0.7231 -0.1082 0.8326 0.054 Uiso 1 1 calc R . . C63 C 0.3752(3) 0.3716(2) 0.0291(3) 0.0796(15) Uani 1 1 d . . . H63A H 0.3691 0.3934 0.0764 0.119 Uiso 1 1 calc R . . H63B H 0.3255 0.3207 0.0061 0.119 Uiso 1 1 calc R . . H63C H 0.3601 0.4094 0.0053 0.119 Uiso 1 1 calc R . . C64 C 0.5612(2) 0.42938(19) 0.0671(2) 0.0476(9) Uani 1 1 d . . . H64A H 0.5644 0.4436 0.1166 0.057 Uiso 1 1 calc R . . H64B H 0.5469 0.4753 0.0527 0.057 Uiso 1 1 calc R . . C65 C 0.6637(2) 0.40852(19) 0.05206(18) 0.0417(8) Uani 1 1 d . . . H65A H 0.6643 0.4019 0.0039 0.050 Uiso 1 1 calc R . . H65B H 0.7230 0.4516 0.0819 0.050 Uiso 1 1 calc R . . C66 C 0.7652(2) 0.3057(2) 0.05061(19) 0.0506(9) Uani 1 1 d . . . H66A H 0.7679 0.3012 0.0036 0.076 Uiso 1 1 calc R . . H66B H 0.7638 0.2533 0.0562 0.076 Uiso 1 1 calc R . . H66C H 0.8267 0.3437 0.0822 0.076 Uiso 1 1 calc R . . C67 C 0.3432(3) 0.1440(2) -0.08662(18) 0.0486(9) Uani 1 1 d . . . H67A H 0.3821 0.1102 -0.1143 0.073 Uiso 1 1 calc R . . H67B H 0.3338 0.1889 -0.1029 0.073 Uiso 1 1 calc R . . H67C H 0.2749 0.1125 -0.0905 0.073 Uiso 1 1 calc R . . C68 C 0.4162(3) 0.11152(19) 0.01350(19) 0.0480(9) Uani 1 1 d . . . H68A H 0.4708 0.0845 -0.0036 0.058 Uiso 1 1 calc R . . H68B H 0.3509 0.0712 0.0008 0.058 Uiso 1 1 calc R . . C69 C 0.4493(3) 0.1516(2) 0.09038(19) 0.0494(9) Uani 1 1 d . . . H69A H 0.3923 0.1745 0.1080 0.059 Uiso 1 1 calc R . . H69B H 0.4674 0.1124 0.1128 0.059 Uiso 1 1 calc R . . C70 C 0.5676(3) 0.2663(2) 0.17586(19) 0.0605(10) Uani 1 1 d . . . H70A H 0.5114 0.2948 0.1855 0.091 Uiso 1 1 calc R . . H70B H 0.6322 0.3050 0.1849 0.091 Uiso 1 1 calc R . . H70C H 0.5771 0.2334 0.2051 0.091 Uiso 1 1 calc R . . C71 C 0.0782(5) 0.6011(3) 0.7362(3) 0.0997(18) Uani 1 1 d . . . H71 H 0.0843 0.6400 0.7794 0.120 Uiso 1 1 calc R . . C72 C 0.1428(4) 0.5443(4) 0.7289(3) 0.0953(17) Uani 1 1 d . . . H72 H 0.1930 0.5449 0.7673 0.114 Uiso 1 1 calc R . . C73 C 0.1322(4) 0.4863(3) 0.6637(3) 0.0798(16) Uani 1 1 d . . . H73 H 0.1746 0.4474 0.6580 0.096 Uiso 1 1 calc R . . C74 C 0.0595(4) 0.4875(2) 0.6091(3) 0.0728(13) Uani 1 1 d . . . H74 H 0.0522 0.4491 0.5654 0.087 Uiso 1 1 calc R . . C75 C -0.0030(4) 0.5434(3) 0.6167(3) 0.0757(13) Uani 1 1 d . . . H75 H -0.0526 0.5435 0.5783 0.091 Uiso 1 1 calc R . . C76 C 0.0066(5) 0.5994(3) 0.6802(3) 0.0957(17) Uani 1 1 d . . . H76 H -0.0372 0.6374 0.6851 0.115 Uiso 1 1 calc R . . C77 C 0.7668(4) 0.9552(2) 0.4493(3) 0.0688(13) Uani 1 1 d . . . H77 H 0.7419 0.8993 0.4277 0.083 Uiso 1 1 calc R . . C78 C 0.8566(3) 0.9846(3) 0.5024(3) 0.0722(14) Uani 1 1 d . . . H78 H 0.8928 0.9484 0.5169 0.087 Uiso 1 1 calc R . . C79 C 0.8926(3) 1.0650(3) 0.5334(2) 0.0668(12) Uani 1 1 d . . . H79 H 0.9541 1.0841 0.5690 0.080 Uiso 1 1 calc R . . C80 C 0.8410(3) 1.1184(2) 0.5136(2) 0.0584(11) Uani 1 1 d . . . H80 H 0.8664 1.1740 0.5361 0.070 Uiso 1 1 calc R . . C81 C 0.7523(3) 1.0919(2) 0.4613(2) 0.0558(10) Uani 1 1 d . . . H81 H 0.7173 1.1293 0.4477 0.067 Uiso 1 1 calc R . . C82 C 0.7142(3) 1.0097(3) 0.42850(19) 0.0609(11) Uani 1 1 d . . . H82 H 0.6533 0.9909 0.3925 0.073 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 Th1 0.02189(5) 0.01976(5) 0.02334(6) 0.00654(4) 0.00340(4) 0.00432(4) Th2 0.01949(5) 0.01907(5) 0.02288(6) 0.00595(4) 0.00297(4) 0.00314(3) Li 0.036(3) 0.034(3) 0.059(4) 0.018(3) 0.014(3) 0.009(2) Cl1 0.0258(3) 0.0216(3) 0.0271(4) 0.0062(3) -0.0004(3) 0.0036(2) Cl2 0.0354(4) 0.0260(3) 0.0308(4) 0.0106(3) 0.0121(3) 0.0098(3) Cl3 0.0218(3) 0.0241(3) 0.0339(4) 0.0111(3) 0.0022(3) 0.0031(2) Cl4 0.0379(4) 0.0257(3) 0.0305(4) 0.0028(3) 0.0078(3) 0.0079(3) Cl5 0.0307(3) 0.0342(4) 0.0271(4) 0.0125(3) 0.0033(3) 0.0053(3) O1 0.0269(9) 0.0282(10) 0.0232(10) 0.0085(8) 0.0054(8) 0.0063(7) O2 0.0244(9) 0.0228(9) 0.0245(10) 0.0033(8) 0.0045(8) 0.0035(7) O3 0.0378(12) 0.0306(12) 0.0621(16) 0.0051(11) 0.0083(11) 0.0067(9) O4 0.0383(12) 0.0337(11) 0.0444(14) 0.0141(10) 0.0097(10) 0.0071(9) O5 0.0447(12) 0.0317(11) 0.0409(13) 0.0102(10) 0.0107(10) 0.0023(9) O6 0.0471(13) 0.0414(13) 0.0450(14) 0.0163(11) 0.0125(11) 0.0071(10) N1 0.0213(10) 0.0228(11) 0.0260(12) 0.0086(9) 0.0055(9) 0.0041(8) N2 0.0269(11) 0.0210(11) 0.0218(12) 0.0079(9) 0.0024(9) 0.0023(9) N3 0.0188(10) 0.0198(11) 0.0269(12) 0.0067(9) 0.0037(9) 0.0023(8) N4 0.0207(10) 0.0213(11) 0.0261(12) 0.0074(9) 0.0036(9) 0.0053(8) C1 0.0240(13) 0.0202(13) 0.0231(14) 0.0043(11) 0.0014(11) 0.0028(10) C2 0.0219(12) 0.0199(13) 0.0247(14) 0.0043(11) 0.0018(10) 0.0040(10) C3 0.0248(13) 0.0254(14) 0.0269(15) 0.0081(11) 0.0076(11) 0.0043(10) C4 0.0286(14) 0.0242(14) 0.0274(15) 0.0090(12) 0.0015(11) 0.0058(11) C5 0.0233(13) 0.0301(15) 0.0323(16) 0.0110(12) 0.0050(12) 0.0068(11) C6 0.0273(14) 0.0228(13) 0.0321(16) 0.0091(12) 0.0087(12) 0.0055(10) C7 0.0281(14) 0.0352(16) 0.0294(16) 0.0112(13) 0.0043(12) 0.0088(12) C8 0.0287(15) 0.0497(19) 0.0383(19) 0.0176(15) 0.0005(13) 0.0109(13) C9 0.0378(17) 0.0488(19) 0.0289(17) 0.0084(15) 0.0029(13) 0.0149(14) C10 0.0370(16) 0.0483(19) 0.0396(19) 0.0232(16) 0.0057(14) 0.0122(14) C11 0.0241(13) 0.0393(17) 0.0331(17) 0.0134(13) 0.0092(12) 0.0089(12) C12 0.0302(16) 0.063(2) 0.043(2) 0.0225(17) 0.0135(14) 0.0134(15) C13 0.0397(17) 0.053(2) 0.0383(19) 0.0112(16) 0.0145(15) 0.0190(15) C14 0.0312(15) 0.0454(18) 0.044(2) 0.0241(16) 0.0106(14) 0.0059(13) C15 0.0305(14) 0.0198(13) 0.0259(15) 0.0104(11) 0.0074(11) 0.0070(10) C16 0.0261(13) 0.0250(14) 0.0286(15) 0.0071(12) 0.0043(11) 0.0083(11) C17 0.0228(13) 0.0287(14) 0.0239(14) 0.0124(12) 0.0022(11) 0.0079(10) C18 0.0304(14) 0.0248(14) 0.0228(15) 0.0038(11) 0.0013(11) 0.0042(11) C19 0.0251(14) 0.0384(17) 0.0382(18) 0.0082(14) 0.0043(13) 0.0016(12) C20 0.0296(14) 0.0219(13) 0.0254(15) 0.0083(11) 0.0053(11) -0.0010(10) C21 0.0362(15) 0.0242(14) 0.0316(17) 0.0099(12) 0.0029(13) 0.0004(11) C22 0.0495(19) 0.0271(16) 0.048(2) 0.0151(15) -0.0006(16) 0.0041(14) C23 0.0496(19) 0.0244(16) 0.046(2) 0.0045(14) -0.0008(16) -0.0022(14) C24 0.0371(16) 0.0294(16) 0.0327(17) 0.0048(13) -0.0020(13) -0.0039(12) C25 0.0266(14) 0.0279(15) 0.0313(16) 0.0091(12) 0.0039(12) -0.0013(11) C26 0.0470(18) 0.0243(15) 0.0341(18) 0.0096(13) -0.0027(14) 0.0067(13) C27 0.0460(19) 0.0372(18) 0.049(2) 0.0122(16) 0.0038(16) 0.0108(14) C28 0.065(2) 0.044(2) 0.041(2) 0.0187(17) -0.0033(17) 0.0104(17) C29 0.0270(14) 0.0293(15) 0.0285(16) 0.0057(12) -0.0006(12) -0.0001(11) C30 0.0326(16) 0.0416(18) 0.0359(18) 0.0150(15) 0.0011(13) 0.0018(13) C31 0.0338(16) 0.0439(18) 0.0336(18) 0.0087(15) 0.0029(13) 0.0039(13) C32 0.0232(12) 0.0221(13) 0.0230(14) 0.0083(11) 0.0029(10) 0.0047(10) C33 0.0203(12) 0.0210(13) 0.0261(15) 0.0074(11) -0.0001(10) 0.0029(10) C34 0.0267(13) 0.0232(13) 0.0263(15) 0.0070(11) 0.0079(11) 0.0077(10) C35 0.0257(13) 0.0233(13) 0.0243(15) 0.0078(11) 0.0031(11) 0.0035(10) C36 0.0227(13) 0.0282(14) 0.0315(16) 0.0088(12) 0.0026(11) -0.0021(11) C37 0.0226(13) 0.0272(14) 0.0290(15) 0.0088(12) 0.0051(11) 0.0056(10) C38 0.0290(14) 0.0232(14) 0.0283(16) 0.0044(12) 0.0039(12) 0.0019(11) C39 0.0423(17) 0.0225(14) 0.0352(18) 0.0034(13) 0.0086(13) 0.0035(12) C40 0.0506(19) 0.0256(15) 0.045(2) 0.0103(14) 0.0174(15) 0.0044(13) C41 0.0383(17) 0.0348(17) 0.0373(19) -0.0013(14) -0.0020(14) 0.0002(13) C42 0.0241(14) 0.0316(15) 0.0372(18) 0.0012(13) 0.0104(12) 0.0013(11) C43 0.0377(16) 0.0349(17) 0.0409(19) 0.0078(14) 0.0196(14) 0.0071(13) C44 0.0264(16) 0.049(2) 0.060(2) -0.0053(17) 0.0176(15) -0.0027(14) C45 0.0291(15) 0.0438(18) 0.0387(19) 0.0071(15) 0.0086(13) 0.0142(13) C46 0.0217(12) 0.0195(13) 0.0280(15) 0.0070(11) 0.0040(11) 0.0059(10) C47 0.0239(13) 0.0225(13) 0.0260(15) 0.0104(11) 0.0017(11) 0.0032(10) C48 0.0218(12) 0.0209(13) 0.0295(15) 0.0082(11) 0.0053(11) 0.0033(10) C49 0.0275(13) 0.0240(13) 0.0232(15) 0.0043(11) 0.0029(11) 0.0032(10) C50 0.0233(14) 0.0503(19) 0.0349(17) 0.0191(15) 0.0082(12) 0.0042(12) C51 0.0217(12) 0.0291(14) 0.0234(14) 0.0107(11) 0.0080(11) 0.0068(10) C52 0.0267(13) 0.0283(14) 0.0245(15) 0.0087(12) 0.0055(11) 0.0036(11) C53 0.0257(14) 0.0391(16) 0.0230(15) 0.0097(13) 0.0046(11) 0.0055(12) C54 0.0321(15) 0.0433(18) 0.0298(16) 0.0194(14) 0.0095(12) 0.0158(13) C55 0.0306(14) 0.0338(15) 0.0304(16) 0.0157(13) 0.0110(12) 0.0128(12) C56 0.0232(13) 0.0298(14) 0.0239(14) 0.0098(12) 0.0094(11) 0.0061(10) C57 0.0313(14) 0.0290(15) 0.0263(16) 0.0069(12) -0.0026(12) 0.0041(11) C58 0.0387(17) 0.0286(16) 0.043(2) 0.0051(14) 0.0073(14) 0.0047(13) C59 0.083(3) 0.0355(19) 0.072(3) 0.0199(19) 0.046(2) 0.0090(18) C60 0.0305(14) 0.0249(14) 0.0320(16) 0.0091(12) 0.0067(12) 0.0076(11) C61 0.0328(15) 0.0275(15) 0.0409(18) 0.0092(13) 0.0118(13) 0.0058(12) C62 0.0318(15) 0.0283(15) 0.051(2) 0.0167(14) 0.0097(14) 0.0052(12) C63 0.039(2) 0.043(2) 0.137(5) 0.003(2) 0.020(2) 0.0083(17) C64 0.0453(19) 0.0304(17) 0.062(2) 0.0101(16) 0.0123(17) 0.0044(14) C65 0.0453(18) 0.0354(17) 0.043(2) 0.0140(15) 0.0083(15) 0.0061(14) C66 0.0390(18) 0.050(2) 0.056(2) 0.0099(18) 0.0067(16) 0.0118(15) C67 0.0450(19) 0.047(2) 0.044(2) 0.0082(17) 0.0100(16) -0.0051(15) C68 0.0459(19) 0.0340(18) 0.065(3) 0.0198(17) 0.0158(17) 0.0014(14) C69 0.0457(19) 0.057(2) 0.057(2) 0.0331(19) 0.0178(17) 0.0065(16) C70 0.084(3) 0.050(2) 0.044(2) 0.0119(18) 0.008(2) 0.020(2) C71 0.160(6) 0.075(4) 0.064(4) 0.016(3) 0.024(4) 0.042(4) C72 0.097(4) 0.112(5) 0.113(5) 0.085(4) 0.030(3) 0.021(3) C73 0.080(3) 0.063(3) 0.141(5) 0.065(3) 0.071(3) 0.032(2) C74 0.083(3) 0.045(2) 0.098(4) 0.017(2) 0.050(3) 0.014(2) C75 0.093(3) 0.054(3) 0.083(4) 0.020(2) 0.030(3) 0.019(2) C76 0.152(5) 0.070(3) 0.081(4) 0.021(3) 0.043(4) 0.065(3) C77 0.076(3) 0.0305(19) 0.095(4) 0.001(2) 0.055(3) -0.0037(19) C78 0.064(3) 0.085(3) 0.111(4) 0.071(3) 0.044(3) 0.040(3) C79 0.044(2) 0.108(4) 0.044(2) 0.024(2) 0.0055(18) 0.011(2) C80 0.055(2) 0.039(2) 0.067(3) -0.0069(19) 0.031(2) -0.0051(17) C81 0.051(2) 0.064(3) 0.081(3) 0.047(2) 0.032(2) 0.0298(19) C82 0.0317(18) 0.098(3) 0.036(2) 0.009(2) 0.0048(15) -0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Th1 O1 2.2031(17) . ? Th1 N1 2.386(2) . ? Th1 N2 2.479(2) . ? Th1 Cl4 2.6756(7) . ? Th1 Cl1 2.8509(6) . ? Th1 Cl3 2.9030(6) . ? Th1 Cl2 2.9343(7) . ? Th1 C15 2.975(3) . ? Th1 C16 3.106(3) . ? Th2 O2 2.2299(17) . ? Th2 N3 2.385(2) . ? Th2 N4 2.507(2) . ? Th2 Cl5 2.6894(7) . ? Th2 Cl1 2.8559(6) . ? Th2 C46 2.917(3) . ? Th2 Cl2 2.9209(7) . ? Th2 Cl3 2.9410(6) . ? Th2 C47 2.997(3) . ? Th2 C48 3.079(3) . ? Li O3 1.933(5) . ? Li O5 1.967(5) . ? Li O4 1.984(5) . ? Li O6 2.003(6) . ? Li C68 2.734(6) . ? Li C65 2.779(6) . ? O1 C1 1.354(3) . ? O2 C32 1.367(3) . ? O3 C63 1.421(4) . ? O3 C64 1.431(4) . ? O4 C66 1.425(4) . ? O4 C65 1.431(4) . ? O5 C67 1.425(4) . ? O5 C68 1.429(4) . ? O6 C70 1.433(4) . ? O6 C69 1.440(4) . ? N1 C15 1.337(3) . ? N1 C2 1.425(3) . ? N2 C17 1.319(3) . ? N2 C20 1.442(3) . ? N3 C46 1.336(3) . ? N3 C33 1.425(3) . ? N4 C48 1.314(3) . ? N4 C51 1.443(3) . ? C1 C6 1.396(4) . ? C1 C2 1.413(4) . ? C2 C3 1.378(4) . ? C3 C4 1.398(4) . ? C3 H3 0.9300 . ? C4 C5 1.396(4) . ? C4 C7 1.540(4) . ? C5 C6 1.403(4) . ? C5 H5 0.9300 . ? C6 C11 1.534(4) . ? C7 C9 1.534(4) . ? C7 C8 1.535(4) . ? C7 C10 1.537(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.528(4) . ? C11 C14 1.534(4) . ? C11 C13 1.545(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.408(4) . ? C15 C18 1.499(3) . ? C16 C17 1.426(4) . ? C16 H16 0.9300 . ? C17 C19 1.496(4) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.393(4) . ? C20 C25 1.404(4) . ? C21 C22 1.400(4) . ? C21 C26 1.533(4) . ? C22 C23 1.373(4) . ? C22 H22 0.9300 . ? C23 C24 1.377(4) . ? C23 H23 0.9300 . ? C24 C25 1.398(4) . ? C24 H24 0.9300 . ? C25 C29 1.523(4) . ? C26 C27 1.520(5) . ? C26 C28 1.531(4) . ? C26 H26 0.9800 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C30 1.524(4) . ? C29 C31 1.529(4) . ? C29 H29 0.9800 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 C33 1.398(4) . ? C32 C37 1.405(3) . ? C33 C34 1.387(3) . ? C34 C35 1.391(3) . ? C34 H34 0.9300 . ? C35 C36 1.392(4) . ? C35 C38 1.541(4) . ? C36 C37 1.394(4) . ? C36 H36 0.9300 . ? C37 C42 1.534(4) . ? C38 C39 1.524(4) . ? C38 C40 1.535(4) . ? C38 C41 1.543(4) . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C40 H40A 0.9600 . ? C40 H40B 0.9600 . ? C40 H40C 0.9600 . ? C41 H41A 0.9600 . ? C41 H41B 0.9600 . ? C41 H41C 0.9600 . ? C42 C44 1.536(4) . ? C42 C45 1.537(4) . ? C42 C43 1.538(4) . ? C43 H43A 0.9600 . ? C43 H43B 0.9600 . ? C43 H43C 0.9600 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 C47 1.410(3) . ? C46 C49 1.505(4) . ? C47 C48 1.433(4) . ? C47 H47 0.9300 . ? C48 C50 1.505(4) . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? C51 C52 1.399(4) . ? C51 C56 1.414(4) . ? C52 C53 1.403(4) . ? C52 C57 1.517(4) . ? C53 C54 1.372(4) . ? C53 H53 0.9300 . ? C54 C55 1.386(4) . ? C54 H54 0.9300 . ? C55 C56 1.392(4) . ? C55 H55 0.9300 . ? C56 C60 1.531(4) . ? C57 C58 1.517(4) . ? C57 C59 1.525(4) . ? C57 H57 0.9800 . ? C58 H58A 0.9600 . ? C58 H58B 0.9600 . ? C58 H58C 0.9600 . ? C59 H59A 0.9600 . ? C59 H59B 0.9600 . ? C59 H59C 0.9600 . ? C60 C61 1.529(4) . ? C60 C62 1.542(4) . ? C60 H60 0.9800 . ? C61 H61A 0.9600 . ? C61 H61B 0.9600 . ? C61 H61C 0.9600 . ? C62 H62A 0.9600 . ? C62 H62B 0.9600 . ? C62 H62C 0.9600 . ? C63 H63A 0.9600 . ? C63 H63B 0.9600 . ? C63 H63C 0.9600 . ? C64 C65 1.496(4) . ? C64 H64A 0.9700 . ? C64 H64B 0.9700 . ? C65 H65A 0.9700 . ? C65 H65B 0.9700 . ? C66 H66A 0.9600 . ? C66 H66B 0.9600 . ? C66 H66C 0.9600 . ? C67 H67A 0.9600 . ? C67 H67B 0.9600 . ? C67 H67C 0.9600 . ? C68 C69 1.486(5) . ? C68 H68A 0.9700 . ? C68 H68B 0.9700 . ? C69 H69A 0.9700 . ? C69 H69B 0.9700 . ? C70 H70A 0.9600 . ? C70 H70B 0.9600 . ? C70 H70C 0.9600 . ? C71 C76 1.342(7) . ? C71 C72 1.384(7) . ? C71 H71 0.9300 . ? C72 C73 1.394(7) . ? C72 H72 0.9300 . ? C73 C74 1.346(7) . ? C73 H73 0.9300 . ? C74 C75 1.352(6) . ? C74 H74 0.9300 . ? C75 C76 1.356(6) . ? C75 H75 0.9300 . ? C76 H76 0.9300 . ? C77 C78 1.371(6) . ? C77 C82 1.377(6) . ? C77 H77 0.9300 . ? C78 C79 1.338(6) . ? C78 H78 0.9300 . ? C79 C80 1.344(6) . ? C79 H79 0.9300 . ? C80 C81 1.353(5) . ? C80 H80 0.9300 . ? C81 C82 1.374(5) . ? C81 H81 0.9300 . ? C82 H82 0.9300 . ? 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 Th1 N1 66.70(7) . . ? O1 Th1 N2 121.74(7) . . ? N1 Th1 N2 71.39(7) . . ? O1 Th1 Cl4 83.74(5) . . ? N1 Th1 Cl4 117.62(5) . . ? N2 Th1 Cl4 81.68(5) . . ? O1 Th1 Cl1 82.34(5) . . ? N1 Th1 Cl1 79.76(5) . . ? N2 Th1 Cl1 127.44(5) . . ? Cl4 Th1 Cl1 150.73(2) . . ? O1 Th1 Cl3 153.08(5) . . ? N1 Th1 Cl3 121.16(5) . . ? N2 Th1 Cl3 83.96(5) . . ? Cl4 Th1 Cl3 110.00(2) . . ? Cl1 Th1 Cl3 74.647(18) . . ? O1 Th1 Cl2 89.68(5) . . ? N1 Th1 Cl2 146.47(5) . . ? N2 Th1 Cl2 141.76(5) . . ? Cl4 Th1 Cl2 80.79(2) . . ? Cl1 Th1 Cl2 73.515(19) . . ? Cl3 Th1 Cl2 70.701(19) . . ? O2 Th2 N3 66.65(7) . . ? O2 Th2 N4 126.88(6) . . ? N3 Th2 N4 73.12(7) . . ? O2 Th2 Cl5 85.94(5) . . ? N3 Th2 Cl5 116.23(5) . . ? N4 Th2 Cl5 82.02(5) . . ? O2 Th2 Cl1 79.31(5) . . ? N3 Th2 Cl1 81.35(5) . . ? N4 Th2 Cl1 127.40(5) . . ? Cl5 Th2 Cl1 150.22(2) . . ? O2 Th2 Cl2 88.66(5) . . ? N3 Th2 Cl2 147.78(5) . . ? N4 Th2 Cl2 138.73(5) . . ? Cl5 Th2 Cl2 80.33(2) . . ? Cl1 Th2 Cl2 73.647(19) . . ? O2 Th2 Cl3 149.68(5) . . ? N3 Th2 Cl3 121.85(5) . . ? N4 Th2 Cl3 81.69(5) . . ? Cl5 Th2 Cl3 110.71(2) . . ? Cl1 Th2 Cl3 73.991(18) . . ? Cl2 Th2 Cl3 70.361(19) . . ? O3 Li O5 103.1(2) . . ? O3 Li O4 83.9(2) . . ? O5 Li O4 172.9(3) . . ? O3 Li O6 122.3(3) . . ? O5 Li O6 83.2(2) . . ? O4 Li O6 93.7(3) . . ? Th1 Cl1 Th2 95.394(19) . . ? Th2 Cl2 Th1 92.25(2) . . ? Th1 Cl3 Th2 92.475(17) . . ? C1 O1 Th1 126.82(16) . . ? C32 O2 Th2 125.56(15) . . ? C63 O3 C64 114.0(2) . . ? C63 O3 Li 127.2(3) . . ? C64 O3 Li 111.5(2) . . ? C66 O4 C65 112.6(2) . . ? C66 O4 Li 120.1(2) . . ? C65 O4 Li 107.8(2) . . ? C67 O5 C68 113.3(2) . . ? C67 O5 Li 126.7(3) . . ? C68 O5 Li 106.1(2) . . ? C70 O6 C69 110.8(3) . . ? C70 O6 Li 123.0(3) . . ? C69 O6 Li 109.8(2) . . ? C15 N1 C2 125.8(2) . . ? C15 N1 Th1 102.42(16) . . ? C2 N1 Th1 118.99(17) . . ? C17 N2 C20 120.6(2) . . ? C17 N2 Th1 108.26(16) . . ? C20 N2 Th1 130.51(17) . . ? C46 N3 C33 123.8(2) . . ? C46 N3 Th2 99.31(15) . . ? C33 N3 Th2 119.28(16) . . ? C48 N4 C51 117.7(2) . . ? C48 N4 Th2 102.87(15) . . ? C51 N4 Th2 138.41(17) . . ? O1 C1 C6 124.0(2) . . ? O1 C1 C2 115.5(2) . . ? C6 C1 C2 120.4(2) . . ? C3 C2 C1 121.0(2) . . ? C3 C2 N1 127.0(2) . . ? C1 C2 N1 111.8(2) . . ? C2 C3 C4 120.1(3) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 118.0(2) . . ? C5 C4 C7 122.8(2) . . ? C3 C4 C7 119.3(3) . . ? C4 C5 C6 123.7(2) . . ? C4 C5 H5 118.2 . . ? C6 C5 H5 118.2 . . ? C1 C6 C5 116.8(3) . . ? C1 C6 C11 119.9(2) . . ? C5 C6 C11 123.3(2) . . ? C9 C7 C8 107.6(2) . . ? C9 C7 C10 108.8(3) . . ? C8 C7 C10 108.0(2) . . ? C9 C7 C4 110.2(2) . . ? C8 C7 C4 112.8(2) . . ? C10 C7 C4 109.3(2) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C14 108.8(2) . . ? C12 C11 C6 112.2(2) . . ? C14 C11 C6 108.1(2) . . ? C12 C11 C13 107.4(2) . . ? C14 C11 C13 109.9(3) . . ? C6 C11 C13 110.5(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 C16 119.8(2) . . ? N1 C15 C18 122.2(2) . . ? C16 C15 C18 117.9(2) . . ? C15 C16 C17 126.4(2) . . ? C15 C16 H16 116.8 . . ? C17 C16 H16 116.8 . . ? N2 C17 C16 120.0(2) . . ? N2 C17 C19 122.4(2) . . ? C16 C17 C19 117.6(2) . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C25 122.1(2) . . ? C21 C20 N2 117.2(2) . . ? C25 C20 N2 120.6(2) . . ? C20 C21 C22 118.0(3) . . ? C20 C21 C26 122.1(2) . . ? C22 C21 C26 119.8(3) . . ? C23 C22 C21 120.7(3) . . ? C23 C22 H22 119.6 . . ? C21 C22 H22 119.6 . . ? C22 C23 C24 120.6(3) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C23 C24 C25 121.0(3) . . ? C23 C24 H24 119.5 . . ? C25 C24 H24 119.5 . . ? C24 C25 C20 117.5(3) . . ? C24 C25 C29 120.0(2) . . ? C20 C25 C29 122.5(2) . . ? C27 C26 C28 112.3(3) . . ? C27 C26 C21 110.3(3) . . ? C28 C26 C21 112.0(3) . . ? C27 C26 H26 107.3 . . ? C28 C26 H26 107.3 . . ? C21 C26 H26 107.3 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 C30 111.2(2) . . ? C25 C29 C31 111.7(2) . . ? C30 C29 C31 110.5(2) . . ? C25 C29 H29 107.8 . . ? C30 C29 H29 107.8 . . ? C31 C29 H29 107.8 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O2 C32 C33 115.8(2) . . ? O2 C32 C37 123.9(2) . . ? C33 C32 C37 120.2(2) . . ? C34 C33 C32 121.2(2) . . ? C34 C33 N3 126.3(2) . . ? C32 C33 N3 112.4(2) . . ? C33 C34 C35 120.2(2) . . ? C33 C34 H34 119.9 . . ? C35 C34 H34 119.9 . . ? C34 C35 C36 117.2(2) . . ? C34 C35 C38 123.7(2) . . ? C36 C35 C38 119.1(2) . . ? C35 C36 C37 124.9(2) . . ? C35 C36 H36 117.5 . . ? C37 C36 H36 117.5 . . ? C36 C37 C32 116.0(2) . . ? C36 C37 C42 122.4(2) . . ? C32 C37 C42 121.6(2) . . ? C39 C38 C40 108.3(2) . . ? C39 C38 C35 112.5(2) . . ? C40 C38 C35 109.3(2) . . ? C39 C38 C41 107.4(2) . . ? C40 C38 C41 108.8(2) . . ? C35 C38 C41 110.3(2) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 C40 H40A 109.5 . . ? C38 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C38 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C38 C41 H41A 109.5 . . ? C38 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C38 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C37 C42 C44 112.0(2) . . ? C37 C42 C45 108.9(2) . . ? C44 C42 C45 107.1(3) . . ? C37 C42 C43 110.3(2) . . ? C44 C42 C43 107.3(3) . . ? C45 C42 C43 111.3(2) . . ? C42 C43 H43A 109.5 . . ? C42 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C42 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? C42 C44 H44A 109.5 . . ? C42 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C42 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C42 C45 H45A 109.5 . . ? C42 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C42 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? N3 C46 C47 120.2(2) . . ? N3 C46 C49 122.7(2) . . ? C47 C46 C49 116.9(2) . . ? C46 C47 C48 126.9(2) . . ? C46 C47 H47 116.5 . . ? C48 C47 H47 116.5 . . ? N4 C48 C47 121.7(2) . . ? N4 C48 C50 122.9(2) . . ? C47 C48 C50 115.4(2) . . ? C46 C49 H49A 109.5 . . ? C46 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C46 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 C50 H50A 109.5 . . ? C48 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C48 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C52 C51 C56 121.8(2) . . ? C52 C51 N4 121.4(2) . . ? C56 C51 N4 116.8(2) . . ? C51 C52 C53 117.5(2) . . ? C51 C52 C57 122.7(2) . . ? C53 C52 C57 119.7(2) . . ? C54 C53 C52 121.7(3) . . ? C54 C53 H53 119.2 . . ? C52 C53 H53 119.2 . . ? C53 C54 C55 119.9(3) . . ? C53 C54 H54 120.0 . . ? C55 C54 H54 120.0 . . ? C54 C55 C56 121.2(3) . . ? C54 C55 H55 119.4 . . ? C56 C55 H55 119.4 . . ? C55 C56 C51 117.8(2) . . ? C55 C56 C60 121.7(2) . . ? C51 C56 C60 120.4(2) . . ? C52 C57 C58 112.0(2) . . ? C52 C57 C59 112.3(3) . . ? C58 C57 C59 109.8(3) . . ? C52 C57 H57 107.5 . . ? C58 C57 H57 107.5 . . ? C59 C57 H57 107.5 . . ? C57 C58 H58A 109.5 . . ? C57 C58 H58B 109.5 . . ? H58A C58 H58B 109.5 . . ? C57 C58 H58C 109.5 . . ? H58A C58 H58C 109.5 . . ? H58B C58 H58C 109.5 . . ? C57 C59 H59A 109.5 . . ? C57 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C57 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C61 C60 C56 114.6(2) . . ? C61 C60 C62 109.7(2) . . ? C56 C60 C62 108.4(2) . . ? C61 C60 H60 108.0 . . ? C56 C60 H60 108.0 . . ? C62 C60 H60 108.0 . . ? C60 C61 H61A 109.5 . . ? C60 C61 H61B 109.5 . . ? H61A C61 H61B 109.5 . . ? C60 C61 H61C 109.5 . . ? H61A C61 H61C 109.5 . . ? H61B C61 H61C 109.5 . . ? C60 C62 H62A 109.5 . . ? C60 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C60 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? O3 C63 H63A 109.5 . . ? O3 C63 H63B 109.5 . . ? H63A C63 H63B 109.5 . . ? O3 C63 H63C 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? O3 C64 C65 106.7(3) . . ? O3 C64 H64A 110.4 . . ? C65 C64 H64A 110.4 . . ? O3 C64 H64B 110.4 . . ? C65 C64 H64B 110.4 . . ? H64A C64 H64B 108.6 . . ? O4 C65 C64 107.1(3) . . ? O4 C65 H65A 110.3 . . ? C64 C65 H65A 110.3 . . ? O4 C65 H65B 110.3 . . ? C64 C65 H65B 110.3 . . ? H65A C65 H65B 108.6 . . ? O4 C66 H66A 109.5 . . ? O4 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? O4 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? O5 C67 H67A 109.5 . . ? O5 C67 H67B 109.5 . . ? H67A C67 H67B 109.5 . . ? O5 C67 H67C 109.5 . . ? H67A C67 H67C 109.5 . . ? H67B C67 H67C 109.5 . . ? O5 C68 C69 106.7(3) . . ? O5 C68 H68A 110.4 . . ? C69 C68 H68A 110.4 . . ? O5 C68 H68B 110.4 . . ? C69 C68 H68B 110.4 . . ? H68A C68 H68B 108.6 . . ? O6 C69 C68 106.8(3) . . ? O6 C69 H69A 110.4 . . ? C68 C69 H69A 110.4 . . ? O6 C69 H69B 110.4 . . ? C68 C69 H69B 110.4 . . ? H69A C69 H69B 108.6 . . ? O6 C70 H70A 109.5 . . ? O6 C70 H70B 109.5 . . ? H70A C70 H70B 109.5 . . ? O6 C70 H70C 109.5 . . ? H70A C70 H70C 109.5 . . ? H70B C70 H70C 109.5 . . ? C76 C71 C72 119.4(5) . . ? C76 C71 H71 120.3 . . ? C72 C71 H71 120.3 . . ? C71 C72 C73 119.4(5) . . ? C71 C72 H72 120.3 . . ? C73 C72 H72 120.3 . . ? C74 C73 C72 119.0(4) . . ? C74 C73 H73 120.5 . . ? C72 C73 H73 120.5 . . ? C73 C74 C75 121.2(5) . . ? C73 C74 H74 119.4 . . ? C75 C74 H74 119.4 . . ? C74 C75 C76 119.9(5) . . ? C74 C75 H75 120.0 . . ? C76 C75 H75 120.0 . . ? C71 C76 C75 121.1(5) . . ? C71 C76 H76 119.4 . . ? C75 C76 H76 119.4 . . ? C78 C77 C82 118.9(4) . . ? C78 C77 H77 120.5 . . ? C82 C77 H77 120.5 . . ? C79 C78 C77 120.6(4) . . ? C79 C78 H78 119.7 . . ? C77 C78 H78 119.7 . . ? C78 C79 C80 120.7(4) . . ? C78 C79 H79 119.7 . . ? C80 C79 H79 119.7 . . ? C79 C80 C81 120.7(4) . . ? C79 C80 H80 119.7 . . ? C81 C80 H80 119.7 . . ? C80 C81 C82 119.6(3) . . ? C80 C81 H81 120.2 . . ? C82 C81 H81 120.2 . . ? C81 C82 C77 119.5(3) . . ? C81 C82 H82 120.2 . . ? C77 C82 H82 120.2 . . ? data_8 _database_code_depnum_ccdc_archive 'CCDC 878338' #TrackingRef '- 878332 878338.txt' _database_code_depnum_ccdc_archive 'CCDC 878338' #TrackingRef 'web_deposit_cif_file_0_PierreThuery_1335341178.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H24 B F4 N' _chemical_formula_weight 305.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7358(7) _cell_length_b 8.3794(4) _cell_length_c 22.5730(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.125(4) _cell_angle_gamma 90.00 _cell_volume 1652.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 48369 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 25.68 _exptl_crystal_description irregular _exptl_crystal_colour 'translucent light yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type none _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and four \w scans with 2\% steps (397 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 48369 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3124 _reflns_number_gt 2437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. Three F atoms are disordered over two sites which have been refined with occupancy parameters constrained to sum to unity and with restraints on displacement parameters and some bond lengths and angles. The H atom bound to N1 was found on a Fourier-difference map and all the others were introduced at calculated positions. All were treated as riding atoms with an isotropic displacement parameter equal to 1.2 (NH, CH) or 1.5 (CH~3~) times that of the parent atom. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0977P)^2^+0.7683P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3124 _refine_ls_number_parameters 223 _refine_ls_number_restraints 106 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0649 _refine_ls_wR_factor_ref 0.1899 _refine_ls_wR_factor_gt 0.1775 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.345 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.523 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.059 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 0.2764(2) 0.2320(3) 0.12611(10) 0.0407(5) Uani 1 1 d . . . H1 H 0.2070 0.3219 0.1335 0.049 Uiso 1 1 d R . . B1 B 0.0908(4) 0.5935(4) 0.16696(15) 0.0504(8) Uani 1 1 d D . . F1 F 0.2380(3) 0.5817(3) 0.14803(13) 0.0946(9) Uani 1 1 d D A . F2A F 0.0201(4) 0.4580(4) 0.13899(19) 0.0697(11) Uani 0.665(6) 1 d PDU A 1 F3A F 0.0178(6) 0.7252(5) 0.1467(3) 0.0966(15) Uani 0.665(6) 1 d PDU A 1 F4A F 0.0666(6) 0.5753(9) 0.22415(19) 0.1175(17) Uani 0.665(6) 1 d PDU A 1 F2B F 0.0488(11) 0.4538(8) 0.1840(5) 0.102(2) Uani 0.335(6) 1 d PDU A 2 F3B F 0.0052(9) 0.6779(13) 0.1347(6) 0.117(3) Uani 0.335(6) 1 d PDU A 2 F4B F 0.1191(10) 0.6834(10) 0.2209(3) 0.088(2) Uani 0.335(6) 1 d PDU A 2 C1 C 0.2537(3) 0.1004(3) 0.15413(12) 0.0418(6) Uani 1 1 d . . . C2 C 0.3563(4) -0.0376(4) 0.14652(15) 0.0561(8) Uani 1 1 d . . . H2A H 0.4339 -0.0119 0.1180 0.084 Uiso 1 1 calc R . . H2B H 0.2983 -0.1277 0.1328 0.084 Uiso 1 1 calc R . . H2C H 0.4036 -0.0630 0.1838 0.084 Uiso 1 1 calc R . . C3 C 0.1202(3) 0.0869(4) 0.19459(14) 0.0520(7) Uani 1 1 d . . . H3A H 0.0647 0.1858 0.1948 0.078 Uiso 1 1 calc R . . H3B H 0.1555 0.0634 0.2339 0.078 Uiso 1 1 calc R . . H3C H 0.0541 0.0027 0.1812 0.078 Uiso 1 1 calc R . . C4 C 0.3964(3) 0.2623(3) 0.08284(12) 0.0390(6) Uani 1 1 d . . . C5 C 0.5345(3) 0.3281(3) 0.10235(12) 0.0414(6) Uani 1 1 d . . . C6 C 0.6452(3) 0.3579(3) 0.05930(13) 0.0455(7) Uani 1 1 d . . . H6 H 0.7394 0.4000 0.0705 0.055 Uiso 1 1 calc R . . C7 C 0.6171(3) 0.3261(3) 0.00024(13) 0.0469(7) Uani 1 1 d . . . H7 H 0.6918 0.3480 -0.0279 0.056 Uiso 1 1 calc R . . C8 C 0.4787(3) 0.2617(3) -0.01718(12) 0.0471(7) Uani 1 1 d . . . H8 H 0.4614 0.2417 -0.0572 0.057 Uiso 1 1 calc R . . C9 C 0.3641(3) 0.2260(3) 0.02352(12) 0.0420(6) Uani 1 1 d . . . C10 C 0.5677(3) 0.3651(4) 0.16701(12) 0.0472(7) Uani 1 1 d . . . H10 H 0.4740 0.3454 0.1897 0.057 Uiso 1 1 calc R . . C11 C 0.6929(4) 0.2548(5) 0.19120(17) 0.0695(10) Uani 1 1 d . . . H11A H 0.6611 0.1457 0.1871 0.104 Uiso 1 1 calc R . . H11B H 0.7104 0.2782 0.2323 0.104 Uiso 1 1 calc R . . H11C H 0.7858 0.2714 0.1694 0.104 Uiso 1 1 calc R . . C12 C 0.6121(4) 0.5400(4) 0.17536(14) 0.0563(8) Uani 1 1 d . . . H12A H 0.7047 0.5617 0.1539 0.084 Uiso 1 1 calc R . . H12B H 0.6282 0.5611 0.2167 0.084 Uiso 1 1 calc R . . H12C H 0.5315 0.6071 0.1607 0.084 Uiso 1 1 calc R . . C13 C 0.2101(3) 0.1571(3) 0.00445(13) 0.0485(7) Uani 1 1 d . . . H13 H 0.1792 0.0796 0.0347 0.058 Uiso 1 1 calc R . . C14 C 0.2169(4) 0.0689(4) -0.05462(15) 0.0596(8) Uani 1 1 d . . . H14A H 0.2345 0.1441 -0.0860 0.089 Uiso 1 1 calc R . . H14B H 0.1216 0.0147 -0.0614 0.089 Uiso 1 1 calc R . . H14C H 0.2987 -0.0074 -0.0537 0.089 Uiso 1 1 calc R . . C15 C 0.0872(4) 0.2869(4) 0.00226(17) 0.0616(9) Uani 1 1 d . . . H15A H 0.0827 0.3403 0.0398 0.092 Uiso 1 1 calc R . . H15B H -0.0103 0.2392 -0.0063 0.092 Uiso 1 1 calc R . . H15C H 0.1120 0.3626 -0.0282 0.092 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 0.0388(11) 0.0366(11) 0.0466(12) -0.0009(9) 0.0063(9) 0.0012(9) B1 0.0537(19) 0.0473(19) 0.0501(19) 0.0005(14) -0.0004(15) 0.0086(15) F1 0.0665(14) 0.0690(14) 0.148(2) -0.0116(14) 0.0300(14) -0.0017(11) F2A 0.0630(18) 0.0501(16) 0.096(3) -0.0139(16) 0.0029(17) -0.0062(13) F3A 0.111(3) 0.0458(19) 0.133(3) -0.017(2) -0.057(2) 0.0252(17) F4A 0.131(3) 0.151(4) 0.070(2) -0.019(3) 0.000(2) 0.029(3) F2B 0.109(4) 0.067(4) 0.130(5) 0.004(4) 0.011(4) -0.003(3) F3B 0.130(5) 0.099(5) 0.120(5) -0.009(5) -0.044(4) 0.036(4) F4B 0.126(5) 0.069(4) 0.069(3) -0.026(3) 0.001(3) 0.024(4) C1 0.0438(14) 0.0415(14) 0.0401(13) -0.0019(11) 0.0017(11) -0.0032(11) C2 0.0622(19) 0.0422(16) 0.0640(19) 0.0090(14) 0.0165(15) 0.0060(13) C3 0.0497(16) 0.0537(17) 0.0527(17) 0.0012(13) 0.0123(13) -0.0045(13) C4 0.0396(13) 0.0334(13) 0.0441(14) 0.0035(10) 0.0066(11) 0.0032(10) C5 0.0421(14) 0.0356(13) 0.0465(15) 0.0055(11) 0.0041(11) 0.0043(11) C6 0.0417(14) 0.0404(14) 0.0543(16) 0.0068(12) 0.0080(12) 0.0020(11) C7 0.0493(16) 0.0418(15) 0.0496(16) 0.0064(12) 0.0134(12) 0.0060(12) C8 0.0571(17) 0.0411(14) 0.0431(15) 0.0019(12) 0.0065(12) 0.0088(12) C9 0.0468(15) 0.0337(13) 0.0455(15) 0.0021(11) 0.0020(11) 0.0063(11) C10 0.0390(14) 0.0565(17) 0.0462(15) 0.0046(13) 0.0003(11) -0.0046(12) C11 0.064(2) 0.077(2) 0.068(2) 0.0185(18) -0.0172(17) 0.0014(18) C12 0.0551(18) 0.0620(19) 0.0519(17) -0.0063(14) 0.0027(14) -0.0100(15) C13 0.0517(16) 0.0443(15) 0.0496(16) 0.0025(12) -0.0031(12) -0.0019(12) C14 0.071(2) 0.0495(17) 0.0585(18) -0.0011(14) -0.0107(16) 0.0015(15) C15 0.0504(17) 0.060(2) 0.074(2) -0.0027(16) -0.0072(15) 0.0049(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.287(4) . ? N1 C4 1.457(3) . ? N1 H1 0.9813 . ? B1 F3B 1.260(7) . ? B1 F2B 1.286(7) . ? B1 F4A 1.317(6) . ? B1 F3A 1.353(5) . ? B1 F1 1.360(4) . ? B1 F2A 1.438(4) . ? B1 F4B 1.452(7) . ? C1 C2 1.473(4) . ? C1 C3 1.487(4) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.396(4) . ? C4 C9 1.401(4) . ? C5 C6 1.395(4) . ? C5 C10 1.519(4) . ? C6 C7 1.381(4) . ? C6 H6 0.9300 . ? C7 C8 1.380(4) . ? C7 H7 0.9300 . ? C8 C9 1.393(4) . ? C8 H8 0.9300 . ? C9 C13 1.525(4) . ? C10 C12 1.528(4) . ? C10 C11 1.532(4) . ? C10 H10 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.526(4) . ? C13 C15 1.529(4) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C4 126.2(2) . . ? C1 N1 H1 118.5 . . ? C4 N1 H1 115.3 . . ? F3B B1 F2B 121.0(6) . . ? F4A B1 F3A 110.5(4) . . ? F3B B1 F1 114.8(6) . . ? F2B B1 F1 107.3(5) . . ? F4A B1 F1 116.9(4) . . ? F3A B1 F1 113.5(4) . . ? F4A B1 F2A 105.6(4) . . ? F3A B1 F2A 107.1(3) . . ? F1 B1 F2A 102.1(3) . . ? F3B B1 F4B 107.1(7) . . ? F2B B1 F4B 105.6(6) . . ? F1 B1 F4B 98.1(4) . . ? N1 C1 C2 121.4(2) . . ? N1 C1 C3 119.3(2) . . ? C2 C1 C3 119.4(2) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C9 124.0(2) . . ? C5 C4 N1 118.7(2) . . ? C9 C4 N1 117.3(2) . . ? C6 C5 C4 116.8(3) . . ? C6 C5 C10 120.1(3) . . ? C4 C5 C10 123.1(2) . . ? C7 C6 C5 121.0(3) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C8 C7 C6 120.3(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 121.8(3) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C8 C9 C4 116.1(3) . . ? C8 C9 C13 122.0(3) . . ? C4 C9 C13 121.9(2) . . ? C5 C10 C12 111.2(2) . . ? C5 C10 C11 110.7(3) . . ? C12 C10 C11 110.7(3) . . ? C5 C10 H10 108.0 . . ? C12 C10 H10 108.0 . . ? C11 C10 H10 108.0 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 C14 113.2(3) . . ? C9 C13 C15 111.0(2) . . ? C14 C13 C15 110.1(3) . . ? C9 C13 H13 107.4 . . ? C14 C13 H13 107.4 . . ? C15 C13 H13 107.4 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 F1 0.98 2.22 2.991(3) 134.6 . N1 H1 F2A 0.98 2.00 2.946(4) 162.7 . N1 H1 F2B 0.98 2.11 3.020(9) 154.4 .