#\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2008-04-28 at 18:34:55 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : f:\progs\wingx\files\archive.dat # CIF files read : sq struct data_sq _audit_creation_date 2008-04-28T18:34:55-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic _publ_requested_category FM #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C42 H54 F24 N4 O10 Y2' _chemical_formula_sum 'C42 H54 F24 N4 O10 Y2' _chemical_formula_weight 1408.71 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 31 2 1' _symmetry_space_group_name_Hall 'P 31 2"' _symmetry_Int_Tables_number 152 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' 'x-y, -y, -z+2/3' '-x, -x+y, -z+1/3' 'y, x, -z' _cell_length_a 24.6268(15) _cell_length_b 24.6268 _cell_length_c 11.0610(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 5809.5(4) _cell_formula_units_Z 3 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6685 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 19.76 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2124 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.588 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_absorpt_correction_T_min 0.382 _exptl_absorpt_correction_T_max 0.953 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.1155 _diffrn_reflns_av_unetI/netI 0.1045 _diffrn_reflns_number 53170 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 8865 _reflns_number_gt 6001 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART, 2006' _computing_cell_refinement 'Bruker SMART, 2006' _computing_data_reduction 'Bruker SAINT, 2006' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # SQUEEZE RESULTS # #----------------------------------------------------------------------------# loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.000 -0.025 2040.1 34.7 _platon_squeeze_details ; ? ; #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 8865 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1152 _refine_ls_goodness_of_fit_ref 0.944 _refine_ls_restrained_S_all 0.944 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.006(6) _refine_diff_density_max 0.345 _refine_diff_density_min -0.506 _refine_diff_density_rms 0.074 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Y1 Y 0.62458(2) 0.087245(19) 0.85023(3) 0.02835(11) Uani 1 d . . . C1 C 0.6776(2) 0.0474(2) 1.0738(4) 0.0345(11) Uani 1 d . . . O1 O 0.69509(16) 0.09021(14) 1.0013(3) 0.0393(8) Uani 1 d . . . O2 O 0.71017(16) 0.04798(15) 1.1675(3) 0.0435(9) Uani 1 d . . . C3 C 0.7701(3) 0.1057(3) 1.1989(4) 0.0545(16) Uani 1 d . . . C4 C 0.8181(3) 0.1167(4) 1.0985(6) 0.078(2) Uani 1 d . . . H4A H 0.8223 0.0793 1.0902 0.118 Uiso 1 calc R . . H4B H 0.8589 0.1527 1.1197 0.118 Uiso 1 calc R . . H4C H 0.8037 0.1249 1.0217 0.118 Uiso 1 calc R . . C5 C 0.7900(3) 0.0860(3) 1.3141(5) 0.076(2) Uani 1 d . . . H5A H 0.7976 0.0514 1.2956 0.115 Uiso 1 calc R . . H5B H 0.7567 0.0722 1.3747 0.115 Uiso 1 calc R . . H5C H 0.8285 0.1216 1.3458 0.115 Uiso 1 calc R . . C6 C 0.7585(3) 0.1594(3) 1.2236(5) 0.0674(19) Uani 1 d . . . H6A H 0.746 0.1713 1.1485 0.101 Uiso 1 calc R . . H6B H 0.7969 0.1953 1.2548 0.101 Uiso 1 calc R . . H6C H 0.7249 0.1463 1.2836 0.101 Uiso 1 calc R . . O7 O 0.59201(15) 0.00668(13) 0.7119(2) 0.0313(7) Uani 1 d . . . C8 C 0.6287(2) 0.0126(2) 0.6082(3) 0.0316(11) Uani 1 d . . . H8 H 0.6724 0.0474 0.6228 0.038 Uiso 1 calc R . . C9 C 0.6036(3) 0.0281(2) 0.4933(4) 0.0414(12) Uani 1 d . . . H9A H 0.6028 0.0672 0.5058 0.062 Uiso 1 calc R . . H9B H 0.561 -0.0061 0.4763 0.062 Uiso 1 calc R . . H9C H 0.6309 0.0332 0.4248 0.062 Uiso 1 calc R . . O11 O 0.71389(15) 0.13959(13) 0.7565(2) 0.0333(7) Uani 1 d . . . C12 C 0.7484(2) 0.1982(2) 0.7172(4) 0.0375(11) Uani 1 d . . . C13 C 0.8050(3) 0.2340(3) 0.8019(5) 0.0519(15) Uani 1 d . . . F13A F 0.84138(16) 0.29561(14) 0.7758(3) 0.0661(10) Uani 1 d . . . F13B F 0.84314(15) 0.21001(16) 0.8014(3) 0.0664(10) Uani 1 d . . . F13C F 0.78524(15) 0.23223(14) 0.9152(3) 0.0582(9) Uani 1 d . . . C14 C 0.7724(3) 0.1970(2) 0.5890(5) 0.0453(13) Uani 1 d . . . F14A F 0.72512(16) 0.17464(14) 0.5093(2) 0.0559(8) Uani 1 d . . . F14B F 0.81527(14) 0.25368(14) 0.5463(3) 0.0576(9) Uani 1 d . . . F14C F 0.79691(16) 0.16013(15) 0.5814(3) 0.0623(9) Uani 1 d . . . C15 C 0.7131(3) 0.2362(2) 0.7149(4) 0.0451(13) Uani 1 d . . . H15A H 0.7072 0.2455 0.7994 0.054 Uiso 1 calc R . . H15B H 0.7404 0.2768 0.6744 0.054 Uiso 1 calc R . . C16 C 0.6494(3) 0.2052(2) 0.6524(4) 0.0394(12) Uani 1 d . . . C17 C 0.6390(3) 0.2437(3) 0.5585(5) 0.0566(16) Uani 1 d . . . H17A H 0.6361 0.2257 0.4783 0.085 Uiso 1 calc R . . H17B H 0.6742 0.2869 0.5602 0.085 Uiso 1 calc R . . H17C H 0.6 0.2436 0.5764 0.085 Uiso 1 calc R . . N18 N 0.6075(2) 0.15051(18) 0.6861(3) 0.0352(9) Uani 1 d . . . C19 C 0.5439(3) 0.1255(2) 0.6376(5) 0.0446(13) Uani 1 d . . . H19A H 0.5439 0.1185 0.5494 0.054 Uiso 1 calc R . . H19B H 0.5293 0.1558 0.6514 0.054 Uiso 1 calc R . . C20 C 0.5009(3) 0.0648(2) 0.6996(5) 0.0466(13) Uani 1 d . . . H20A H 0.4567 0.0537 0.6868 0.056 Uiso 1 calc R . . H20B H 0.5067 0.0308 0.6657 0.056 Uiso 1 calc R . . N21 N 0.5155(2) 0.07199(18) 0.8298(4) 0.0371(9) Uani 1 d . . . C22 C 0.4890(3) 0.0914(2) 0.9029(5) 0.0487(13) Uani 1 d . . . C23 C 0.4367(3) 0.1040(4) 0.8698(7) 0.080(2) Uani 1 d . . . H23A H 0.441 0.117 0.7849 0.121 Uiso 1 calc R . . H23B H 0.4389 0.1374 0.9215 0.121 Uiso 1 calc R . . H23C H 0.3961 0.0657 0.8814 0.121 Uiso 1 calc R . . C24 C 0.5127(3) 0.1069(2) 1.0303(5) 0.0501(14) Uani 1 d . . . H24A H 0.5113 0.0696 1.0676 0.06 Uiso 1 calc R . . H24B H 0.4847 0.1169 1.0774 0.06 Uiso 1 calc R . . O31 O 0.62190(17) 0.15391(15) 0.9750(3) 0.0457(9) Uani 1 d . . . C32 C 0.5801(2) 0.1625(2) 1.0378(5) 0.0431(13) Uani 1 d . . . C33 C 0.5990(3) 0.1710(3) 1.1714(5) 0.0583(17) Uani 1 d . . . F33A F 0.59721(17) 0.11963(14) 1.2163(3) 0.0599(8) Uani 1 d . . . F33B F 0.65727(19) 0.21776(16) 1.1943(3) 0.0766(12) Uani 1 d . . . F33C F 0.56088(19) 0.18163(16) 1.2445(3) 0.0751(11) Uani 1 d . . . C34 C 0.5827(3) 0.2233(2) 0.9920(5) 0.0550(16) Uani 1 d . . . F34A F 0.63745(18) 0.27486(14) 1.0100(3) 0.0757(11) Uani 1 d . . . F34B F 0.53962(19) 0.23367(15) 1.0449(3) 0.0737(11) Uani 1 d . . . F34C F 0.57190(19) 0.22007(15) 0.8733(3) 0.0743(11) Uani 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Y1 0.0371(3) 0.0192(2) 0.02407(18) -0.00199(19) 0.0040(2) 0.0106(2) C1 0.046(3) 0.022(2) 0.0182(19) -0.0047(19) 0.000(2) 0.005(2) O1 0.044(2) 0.0283(17) 0.0280(16) -0.0034(14) 0.0011(15) 0.0045(16) O2 0.046(2) 0.0348(19) 0.0260(17) -0.0027(14) -0.0117(15) 0.0028(16) C3 0.051(3) 0.040(3) 0.035(3) -0.001(2) -0.015(3) -0.005(3) C4 0.045(4) 0.091(5) 0.064(4) 0.009(4) -0.014(3) 0.007(4) C5 0.070(4) 0.067(4) 0.050(3) 0.005(3) -0.033(3) 0.003(3) C6 0.095(5) 0.033(3) 0.039(3) -0.006(3) -0.016(3) 0.005(3) O7 0.045(2) 0.0228(15) 0.0221(14) 0.0008(12) 0.0009(14) 0.0145(15) C8 0.046(3) 0.029(3) 0.017(2) 0.0005(18) -0.0008(19) 0.017(2) C9 0.064(4) 0.039(3) 0.023(2) 0.001(2) -0.001(2) 0.027(3) O11 0.047(2) 0.0203(16) 0.0288(14) -0.0013(12) 0.0086(14) 0.0137(16) C12 0.050(3) 0.027(2) 0.027(2) 0.0032(19) 0.013(2) 0.014(2) C13 0.055(4) 0.033(3) 0.049(3) -0.001(3) 0.006(3) 0.008(3) F13A 0.063(2) 0.0347(18) 0.066(2) -0.0014(16) 0.0096(17) -0.0015(16) F13B 0.049(2) 0.054(2) 0.083(2) -0.0022(18) -0.0008(17) 0.0149(18) F13C 0.065(2) 0.0494(19) 0.0389(16) -0.0066(14) -0.0025(15) 0.0122(17) C14 0.054(4) 0.042(3) 0.037(3) 0.005(2) 0.019(3) 0.022(3) F14A 0.076(2) 0.0582(19) 0.0304(14) -0.0052(13) 0.0134(16) 0.0309(18) F14B 0.066(2) 0.0452(19) 0.0489(17) 0.0161(15) 0.0279(16) 0.0183(17) F14C 0.085(3) 0.062(2) 0.0544(18) 0.0107(16) 0.0320(18) 0.048(2) C15 0.055(4) 0.027(3) 0.042(3) 0.003(2) 0.022(3) 0.012(3) C16 0.058(4) 0.028(3) 0.038(3) 0.006(2) 0.020(2) 0.025(3) C17 0.092(5) 0.039(3) 0.045(3) 0.017(2) 0.013(3) 0.037(3) N18 0.050(3) 0.025(2) 0.035(2) 0.0009(17) 0.0029(19) 0.022(2) C19 0.058(4) 0.035(3) 0.050(3) 0.002(2) 0.000(3) 0.030(3) C20 0.050(3) 0.039(3) 0.056(3) -0.001(2) -0.003(3) 0.026(3) N21 0.042(2) 0.024(2) 0.047(2) 0.0045(18) 0.008(2) 0.0171(19) C22 0.042(3) 0.033(3) 0.068(4) 0.004(3) 0.014(3) 0.016(3) C23 0.073(5) 0.088(5) 0.110(6) 0.011(5) 0.024(4) 0.063(4) C24 0.054(4) 0.037(3) 0.061(3) 0.007(3) 0.028(3) 0.024(3) O31 0.051(2) 0.0295(19) 0.046(2) -0.0076(16) 0.0175(17) 0.0126(17) C32 0.054(3) 0.027(3) 0.049(3) -0.005(2) 0.019(3) 0.021(3) C33 0.082(5) 0.026(3) 0.058(4) -0.006(3) 0.022(3) 0.021(3) F33A 0.083(2) 0.0420(19) 0.0533(17) -0.0071(16) 0.0091(17) 0.0302(17) F33B 0.093(3) 0.050(2) 0.056(2) -0.0233(16) 0.0125(19) 0.012(2) F33C 0.113(3) 0.069(2) 0.059(2) -0.0024(17) 0.038(2) 0.057(2) C34 0.070(4) 0.033(3) 0.058(4) -0.001(3) 0.029(3) 0.022(3) F34A 0.098(3) 0.0265(17) 0.082(2) -0.0053(16) 0.038(2) 0.0153(19) F34B 0.109(3) 0.052(2) 0.078(2) 0.0111(17) 0.047(2) 0.053(2) F34C 0.127(3) 0.044(2) 0.060(2) 0.0094(16) 0.035(2) 0.049(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Y1 O31 2.171(3) . ? Y1 O11 2.177(3) . ? Y1 O7 2.309(3) . ? Y1 O7 2.321(3) 4_556 ? Y1 O1 2.384(3) . ? Y1 N21 2.529(4) . ? Y1 N18 2.560(4) . ? Y1 Y1 3.7402(8) 4_556 ? C1 O1 1.219(5) . ? C1 O2 1.307(5) . ? C1 C8 1.506(6) 4_556 ? O2 C3 1.491(6) . ? C3 C6 1.510(9) . ? C3 C5 1.529(7) . ? C3 C4 1.545(9) . ? C4 H4A 0.98 . ? C4 H4B 0.98 . ? C4 H4C 0.98 . ? C5 H5A 0.98 . ? C5 H5B 0.98 . ? C5 H5C 0.98 . ? C6 H6A 0.98 . ? C6 H6B 0.98 . ? C6 H6C 0.98 . ? O7 C8 1.421(5) . ? O7 Y1 2.321(3) 4_556 ? C8 C1 1.506(6) 4_556 ? C8 C9 1.543(6) . ? C8 H8 1 . ? C9 H9A 0.98 . ? C9 H9B 0.98 . ? C9 H9C 0.98 . ? O11 C12 1.330(5) . ? C12 C13 1.540(8) . ? C12 C14 1.542(6) . ? C12 C15 1.563(7) . ? C13 F13B 1.336(7) . ? C13 F13C 1.338(6) . ? C13 F13A 1.352(6) . ? C14 F14C 1.321(6) . ? C14 F14A 1.339(6) . ? C14 F14B 1.346(6) . ? C15 C16 1.524(8) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C16 N18 1.275(6) . ? C16 C17 1.513(7) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? N18 C19 1.469(6) . ? C19 C20 1.497(7) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 N21 1.474(6) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? N21 C22 1.273(6) . ? C22 C24 1.500(8) . ? C22 C23 1.514(8) . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 C32 1.537(7) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? O31 C32 1.343(6) . ? C32 C33 1.533(8) . ? C32 C34 1.553(7) . ? C33 F33A 1.339(6) . ? C33 F33B 1.340(7) . ? C33 F33C 1.360(6) . ? C34 F34A 1.326(7) . ? C34 F34C 1.334(6) . ? C34 F34B 1.342(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O31 Y1 O11 104.99(11) . . ? O31 Y1 O7 160.46(13) . . ? O11 Y1 O7 90.41(10) . . ? O31 Y1 O7 106.37(11) . 4_556 ? O11 Y1 O7 128.43(11) . 4_556 ? O7 Y1 O7 71.42(10) . 4_556 ? O31 Y1 O1 80.12(13) . . ? O11 Y1 O1 79.10(11) . . ? O7 Y1 O1 115.19(11) . . ? O7 Y1 O1 67.38(10) 4_556 . ? O31 Y1 N21 74.78(13) . . ? O11 Y1 N21 136.80(12) . . ? O7 Y1 N21 85.78(12) . . ? O7 Y1 N21 90.82(12) 4_556 . ? O1 Y1 N21 140.36(12) . . ? O31 Y1 N18 85.09(13) . . ? O11 Y1 N18 74.13(12) . . ? O7 Y1 N18 87.74(10) . . ? O7 Y1 N18 147.85(12) 4_556 . ? O1 Y1 N18 144.77(12) . . ? N21 Y1 N18 62.74(13) . . ? O31 Y1 Y1 135.66(9) . 4_556 ? O11 Y1 Y1 117.56(7) . 4_556 ? O7 Y1 Y1 36.23(7) . 4_556 ? O7 Y1 Y1 36.01(7) 4_556 4_556 ? O1 Y1 Y1 95.53(7) . 4_556 ? N21 Y1 Y1 82.13(9) . 4_556 ? N18 Y1 Y1 116.97(9) . 4_556 ? O1 C1 O2 124.3(4) . . ? O1 C1 C8 121.5(4) . 4_556 ? O2 C1 C8 114.2(4) . 4_556 ? C1 O1 Y1 119.8(3) . . ? C1 O2 C3 120.3(4) . . ? O2 C3 C6 110.3(5) . . ? O2 C3 C5 102.2(4) . . ? C6 C3 C5 111.0(5) . . ? O2 C3 C4 107.8(4) . . ? C6 C3 C4 116.2(5) . . ? C5 C3 C4 108.4(6) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C8 O7 Y1 121.1(2) . . ? C8 O7 Y1 121.8(2) . 4_556 ? Y1 O7 Y1 107.77(10) . 4_556 ? O7 C8 C1 108.4(3) . 4_556 ? O7 C8 C9 112.2(4) . . ? C1 C8 C9 111.2(3) 4_556 . ? O7 C8 H8 108.3 . . ? C1 C8 H8 108.3 4_556 . ? C9 C8 H8 108.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C12 O11 Y1 134.9(3) . . ? O11 C12 C13 109.0(4) . . ? O11 C12 C14 108.8(4) . . ? C13 C12 C14 108.9(4) . . ? O11 C12 C15 114.2(4) . . ? C13 C12 C15 106.5(4) . . ? C14 C12 C15 109.2(4) . . ? F13B C13 F13C 108.3(5) . . ? F13B C13 F13A 106.2(5) . . ? F13C C13 F13A 105.2(4) . . ? F13B C13 C12 112.4(4) . . ? F13C C13 C12 109.9(4) . . ? F13A C13 C12 114.5(5) . . ? F14C C14 F14A 106.1(4) . . ? F14C C14 F14B 107.4(4) . . ? F14A C14 F14B 105.4(4) . . ? F14C C14 C12 112.5(4) . . ? F14A C14 C12 110.5(4) . . ? F14B C14 C12 114.3(4) . . ? C16 C15 C12 116.6(4) . . ? C16 C15 H15A 108.1 . . ? C12 C15 H15A 108.1 . . ? C16 C15 H15B 108.1 . . ? C12 C15 H15B 108.1 . . ? H15A C15 H15B 107.3 . . ? N18 C16 C17 124.2(5) . . ? N18 C16 C15 118.9(4) . . ? C17 C16 C15 116.8(4) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 N18 C19 117.8(4) . . ? C16 N18 Y1 123.9(4) . . ? C19 N18 Y1 117.9(3) . . ? N18 C19 C20 109.0(4) . . ? N18 C19 H19A 109.9 . . ? C20 C19 H19A 109.9 . . ? N18 C19 H19B 109.9 . . ? C20 C19 H19B 109.9 . . ? H19A C19 H19B 108.3 . . ? N21 C20 C19 108.6(4) . . ? N21 C20 H20A 110 . . ? C19 C20 H20A 110 . . ? N21 C20 H20B 110 . . ? C19 C20 H20B 110 . . ? H20A C20 H20B 108.3 . . ? C22 N21 C20 121.7(5) . . ? C22 N21 Y1 126.4(4) . . ? C20 N21 Y1 106.4(3) . . ? N21 C22 C24 119.0(5) . . ? N21 C22 C23 124.9(6) . . ? C24 C22 C23 116.0(5) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 C32 112.8(4) . . ? C22 C24 H24A 109 . . ? C32 C24 H24A 109 . . ? C22 C24 H24B 109 . . ? C32 C24 H24B 109 . . ? H24A C24 H24B 107.8 . . ? C32 O31 Y1 139.7(3) . . ? O31 C32 C33 108.4(5) . . ? O31 C32 C24 113.7(4) . . ? C33 C32 C24 107.0(4) . . ? O31 C32 C34 108.6(4) . . ? C33 C32 C34 108.6(4) . . ? C24 C32 C34 110.3(5) . . ? F33A C33 F33B 104.9(6) . . ? F33A C33 F33C 105.2(4) . . ? F33B C33 F33C 105.6(4) . . ? F33A C33 C32 111.3(4) . . ? F33B C33 C32 115.0(5) . . ? F33C C33 C32 114.0(5) . . ? F34A C34 F34C 106.4(4) . . ? F34A C34 F34B 106.0(4) . . ? F34C C34 F34B 106.8(5) . . ? F34A C34 C32 113.9(5) . . ? F34C C34 C32 110.6(4) . . ? F34B C34 C32 112.7(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 O1 Y1 -172.1(3) . . . . ? C8 C1 O1 Y1 10.3(6) 4_556 . . . ? O31 Y1 O1 C1 102.8(3) . . . . ? O11 Y1 O1 C1 -149.7(3) . . . . ? O7 Y1 O1 C1 -64.4(3) . . . . ? O7 Y1 O1 C1 -9.7(3) 4_556 . . . ? N21 Y1 O1 C1 51.7(4) . . . . ? N18 Y1 O1 C1 169.4(3) . . . . ? Y1 Y1 O1 C1 -32.6(3) 4_556 . . . ? O1 C1 O2 C3 6.3(7) . . . . ? C8 C1 O2 C3 -176.0(4) 4_556 . . . ? C1 O2 C3 C6 59.9(6) . . . . ? C1 O2 C3 C5 178.1(5) . . . . ? C1 O2 C3 C4 -67.9(6) . . . . ? O31 Y1 O7 C8 136.1(4) . . . . ? O11 Y1 O7 C8 -6.4(3) . . . . ? O7 Y1 O7 C8 -137.2(3) 4_556 . . . ? O1 Y1 O7 C8 -84.6(3) . . . . ? N21 Y1 O7 C8 130.5(3) . . . . ? N18 Y1 O7 C8 67.7(3) . . . . ? Y1 Y1 O7 C8 -147.1(4) 4_556 . . . ? O31 Y1 O7 Y1 -76.8(4) . . . 4_556 ? O11 Y1 O7 Y1 140.63(14) . . . 4_556 ? O7 Y1 O7 Y1 9.84(17) 4_556 . . 4_556 ? O1 Y1 O7 Y1 62.50(16) . . . 4_556 ? N21 Y1 O7 Y1 -82.44(14) . . . 4_556 ? N18 Y1 O7 Y1 -145.27(15) . . . 4_556 ? Y1 O7 C8 C1 136.1(3) . . . 4_556 ? Y1 O7 C8 C1 -6.4(5) 4_556 . . 4_556 ? Y1 O7 C8 C9 -100.7(4) . . . . ? Y1 O7 C8 C9 116.8(3) 4_556 . . . ? O31 Y1 O11 C12 -36.3(4) . . . . ? O7 Y1 O11 C12 131.6(4) . . . . ? O7 Y1 O11 C12 -162.1(4) 4_556 . . . ? O1 Y1 O11 C12 -112.8(4) . . . . ? N21 Y1 O11 C12 47.3(4) . . . . ? N18 Y1 O11 C12 44.0(4) . . . . ? Y1 Y1 O11 C12 156.6(4) 4_556 . . . ? Y1 O11 C12 C13 105.3(5) . . . . ? Y1 O11 C12 C14 -136.0(4) . . . . ? Y1 O11 C12 C15 -13.6(6) . . . . ? O11 C12 C13 F13B 63.2(5) . . . . ? C14 C12 C13 F13B -55.5(5) . . . . ? C15 C12 C13 F13B -173.1(4) . . . . ? O11 C12 C13 F13C -57.5(6) . . . . ? C14 C12 C13 F13C -176.1(4) . . . . ? C15 C12 C13 F13C 66.2(5) . . . . ? O11 C12 C13 F13A -175.6(4) . . . . ? C14 C12 C13 F13A 65.7(6) . . . . ? C15 C12 C13 F13A -51.9(6) . . . . ? O11 C12 C14 F14C -47.9(6) . . . . ? C13 C12 C14 F14C 70.8(5) . . . . ? C15 C12 C14 F14C -173.3(4) . . . . ? O11 C12 C14 F14A 70.5(5) . . . . ? C13 C12 C14 F14A -170.8(4) . . . . ? C15 C12 C14 F14A -54.9(5) . . . . ? O11 C12 C14 F14B -170.8(4) . . . . ? C13 C12 C14 F14B -52.0(6) . . . . ? C15 C12 C14 F14B 63.9(6) . . . . ? O11 C12 C15 C16 -50.5(5) . . . . ? C13 C12 C15 C16 -170.9(4) . . . . ? C14 C12 C15 C16 71.6(5) . . . . ? C12 C15 C16 N18 54.5(6) . . . . ? C12 C15 C16 C17 -129.2(4) . . . . ? C17 C16 N18 C19 -4.9(7) . . . . ? C15 C16 N18 C19 171.2(4) . . . . ? C17 C16 N18 Y1 -177.8(3) . . . . ? C15 C16 N18 Y1 -1.7(6) . . . . ? O31 Y1 N18 C16 72.4(4) . . . . ? O11 Y1 N18 C16 -34.7(4) . . . . ? O7 Y1 N18 C16 -125.8(4) . . . . ? O7 Y1 N18 C16 -174.4(3) 4_556 . . . ? O1 Y1 N18 C16 7.2(5) . . . . ? N21 Y1 N18 C16 147.8(4) . . . . ? Y1 Y1 N18 C16 -148.0(3) 4_556 . . . ? O31 Y1 N18 C19 -100.5(3) . . . . ? O11 Y1 N18 C19 152.4(3) . . . . ? O7 Y1 N18 C19 61.3(3) . . . . ? O7 Y1 N18 C19 12.7(4) 4_556 . . . ? O1 Y1 N18 C19 -165.7(3) . . . . ? N21 Y1 N18 C19 -25.1(3) . . . . ? Y1 Y1 N18 C19 39.1(3) 4_556 . . . ? C16 N18 C19 C20 -173.2(4) . . . . ? Y1 N18 C19 C20 0.1(5) . . . . ? N18 C19 C20 N21 42.9(5) . . . . ? C19 C20 N21 C22 89.2(6) . . . . ? C19 C20 N21 Y1 -66.3(4) . . . . ? O31 Y1 N21 C22 -15.9(4) . . . . ? O11 Y1 N21 C22 -111.7(4) . . . . ? O7 Y1 N21 C22 162.2(4) . . . . ? O7 Y1 N21 C22 90.9(4) 4_556 . . . ? O1 Y1 N21 C22 36.7(5) . . . . ? N18 Y1 N21 C22 -108.2(4) . . . . ? Y1 Y1 N21 C22 125.9(4) 4_556 . . . ? O31 Y1 N21 C20 138.1(3) . . . . ? O11 Y1 N21 C20 42.2(3) . . . . ? O7 Y1 N21 C20 -43.9(3) . . . . ? O7 Y1 N21 C20 -115.2(3) 4_556 . . . ? O1 Y1 N21 C20 -169.3(3) . . . . ? N18 Y1 N21 C20 45.8(3) . . . . ? Y1 Y1 N21 C20 -80.1(3) 4_556 . . . ? C20 N21 C22 C24 -170.9(4) . . . . ? Y1 N21 C22 C24 -20.6(6) . . . . ? C20 N21 C22 C23 5.3(8) . . . . ? Y1 N21 C22 C23 155.6(5) . . . . ? N21 C22 C24 C32 64.5(6) . . . . ? C23 C22 C24 C32 -112.0(6) . . . . ? O11 Y1 O31 C32 158.9(5) . . . . ? O7 Y1 O31 C32 18.0(7) . . . . ? O7 Y1 O31 C32 -62.5(5) 4_556 . . . ? O1 Y1 O31 C32 -125.3(5) . . . . ? N21 Y1 O31 C32 23.8(5) . . . . ? N18 Y1 O31 C32 86.8(5) . . . . ? Y1 Y1 O31 C32 -37.5(6) 4_556 . . . ? Y1 O31 C32 C33 125.2(5) . . . . ? Y1 O31 C32 C24 6.3(8) . . . . ? Y1 O31 C32 C34 -116.9(5) . . . . ? C22 C24 C32 O31 -57.8(6) . . . . ? C22 C24 C32 C33 -177.5(4) . . . . ? C22 C24 C32 C34 64.5(5) . . . . ? O31 C32 C33 F33A -62.7(6) . . . . ? C24 C32 C33 F33A 60.4(6) . . . . ? C34 C32 C33 F33A 179.5(5) . . . . ? O31 C32 C33 F33B 56.4(6) . . . . ? C24 C32 C33 F33B 179.5(5) . . . . ? C34 C32 C33 F33B -61.4(6) . . . . ? O31 C32 C33 F33C 178.6(4) . . . . ? C24 C32 C33 F33C -58.4(6) . . . . ? C34 C32 C33 F33C 60.7(6) . . . . ? O31 C32 C34 F34A -62.9(6) . . . . ? C33 C32 C34 F34A 54.8(6) . . . . ? C24 C32 C34 F34A 171.8(4) . . . . ? O31 C32 C34 F34C 56.8(6) . . . . ? C33 C32 C34 F34C 174.5(5) . . . . ? C24 C32 C34 F34C -68.5(6) . . . . ? O31 C32 C34 F34B 176.3(4) . . . . ? C33 C32 C34 F34B -66.0(6) . . . . ? C24 C32 C34 F34B 51.0(6) . . . . ?