# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 # #------------------------------------------------------------------------- #2 Person making the deposition # _publ_contact_author 'Venkataraman, Dhandapani' _publ_contact_author_email dv@chem.umass.edu _ccdc_journal_depnumber ? _publ_section_title ;Segregated assemblies of electron-rich and electron-poor pi-conjugated molecules ; _publ_requested_category FO _publ_contact_author_name 'Dhandapani Venkataraman' loop_ _publ_author_name D.Venkataraman T.Benanti P.Saejueng data_struct_615872 _database_code_depnum_ccdc_archive 'CCDC 615872' _audit_creation_date 2006-10-14T10:55:46-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C36 H22 F7 N1 O3' _chemical_formula_weight 649.55 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.6784(8) _cell_length_b 8.4377(11) _cell_length_c 31.313(5) _cell_angle_alpha 87.186(6) _cell_angle_beta 87.102(5) _cell_angle_gamma 79.417(8) _cell_volume 1471.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293 _cell_measurement_reflns_used 3794 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.025 _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 664 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.37814E-1 _diffrn_orient_matrix_ub_12 -0.344276E-1 _diffrn_orient_matrix_ub_13 -0.285934E-1 _diffrn_orient_matrix_ub_21 0.174617 _diffrn_orient_matrix_ub_22 -0.200184E-1 _diffrn_orient_matrix_ub_23 -0.85887E-2 _diffrn_orient_matrix_ub_31 0.152432E-1 _diffrn_orient_matrix_ub_32 -0.113904 _diffrn_orient_matrix_ub_33 0.115263E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.067 _diffrn_reflns_number 5147 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.3 _diffrn_reflns_theta_max 25.75 _diffrn_reflns_theta_full 25.75 _diffrn_measured_fraction_theta_full 0.914 _diffrn_measured_fraction_theta_max 0.914 _reflns_number_total 5147 _reflns_number_gt 2667 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; 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. The fluorine atoms on the terminal carbon and the penultimate carbon of the fluorocarbon chain were modeled as disordered over two sites; the occupancy factor was set to 0.5 on each site and was not refined. The bond length of the carbon-fluorine bond was restrained to be 1.35 A using the DFIX command in SHELXL with a standard deviation of 0.02. The distance between the fluorines on carbon C35 (penultimate carbon of the chain) was restrained to be 2.20 A using DANG command with 0.04 as the standard deviation. The distance between the fluorine atoms on the terminal carbon were restrained to be the same using SADI command with 0.02 as standard deviation. No restraints were placed on the anisoptropic refinement of the fluorine atoms. SHELXL output (.LST) suggests more disorder in the fluorine atoms of the terminal and penultimate carbon atoms but were not included in the final model. ; _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^)+(0.0630P)^2^+2.4533P] 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 noref _refine_ls_extinction_method none _refine_ls_number_reflns 5147 _refine_ls_number_parameters 469 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1842 _refine_ls_R_factor_gt 0.0924 _refine_ls_wR_factor_ref 0.2428 _refine_ls_wR_factor_gt 0.1918 _refine_ls_goodness_of_fit_ref 1.151 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.337 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.054 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_number_in_cell C 72 H 44 F 14 N 2 O 6 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 C1 C -0.1516(9) 1.3390(6) 0.35265(16) 0.0546(14) Uani 1 1 d . . . C2 C -0.3578(9) 1.4507(6) 0.34819(16) 0.0537(13) Uani 1 1 d . . . H2 H -0.4742 1.4294 0.3305 0.064 Uiso 1 1 calc R . . C3 C -0.6045(9) 1.7184(6) 0.36346(16) 0.0547(13) Uani 1 1 d . . . H3 H -0.7228 1.7 0.3458 0.066 Uiso 1 1 calc R . . C4 C -0.6312(9) 1.8612(6) 0.38304(16) 0.0562(14) Uani 1 1 d . . . H4 H -0.7674 1.9394 0.3788 0.067 Uiso 1 1 calc R . . C5 C -0.4545(9) 1.8909(6) 0.40962(16) 0.0540(13) Uani 1 1 d . . . C6 C -0.2557(9) 1.7776(6) 0.41687(16) 0.0543(13) Uani 1 1 d . . . H6 H -0.1414 1.7985 0.435 0.065 Uiso 1 1 calc R . . C7 C -0.0155(9) 1.5071(6) 0.40203(17) 0.0564(14) Uani 1 1 d . . . H7 H 0.0991 1.5236 0.4207 0.068 Uiso 1 1 calc R . . C8 C 0.0201(9) 1.3685(6) 0.38063(17) 0.0589(14) Uani 1 1 d . . . H8 H 0.159 1.2923 0.3845 0.071 Uiso 1 1 calc R . . C9 C -0.3984(9) 1.5967(6) 0.36953(15) 0.0468(12) Uani 1 1 d . . . C10 C -0.2220(8) 1.6277(6) 0.39678(15) 0.0465(12) Uani 1 1 d . . . C11 C -0.3255(10) 2.0844(6) 0.45237(18) 0.0616(15) Uani 1 1 d . . . H11A H -0.1761 2.0797 0.4356 0.074 Uiso 1 1 calc R . . H11B H -0.2968 2.0103 0.477 0.074 Uiso 1 1 calc R . . C12 C -0.4139(10) 2.2530(6) 0.46679(18) 0.0634(15) Uani 1 1 d . . . H12A H -0.5704 2.259 0.4812 0.076 Uiso 1 1 calc R . . H12B H -0.4307 2.3275 0.4421 0.076 Uiso 1 1 calc R . . C13 C -0.2415(11) 2.3012(7) 0.49684(19) 0.0800(18) Uani 1 1 d . . . H13A H -0.2993 2.4098 0.5052 0.12 Uiso 1 1 calc R . . H13B H -0.0865 2.2945 0.4826 0.12 Uiso 1 1 calc R . . H13C H -0.2294 2.2297 0.5218 0.12 Uiso 1 1 calc R . . C14 C -0.1063(10) 1.1946(7) 0.32866(17) 0.0579(14) Uani 1 1 d . . . C15 C -0.0619(10) 1.0764(7) 0.30823(17) 0.0593(14) Uani 1 1 d . . . C16 C -0.0069(9) 0.9345(6) 0.28367(16) 0.0535(13) Uani 1 1 d . . . C17 C 0.1949(9) 0.9075(7) 0.25636(17) 0.0592(14) Uani 1 1 d . . . H17 H 0.2974 0.982 0.2544 0.071 Uiso 1 1 calc R . . C18 C 0.2469(10) 0.7724(7) 0.23204(17) 0.0603(15) Uani 1 1 d . . . H18 H 0.3818 0.7563 0.2135 0.072 Uiso 1 1 calc R . . C19 C 0.0956(9) 0.6620(6) 0.23568(16) 0.0493(13) Uani 1 1 d . . . C20 C -0.1050(10) 0.6845(6) 0.26257(17) 0.0573(14) Uani 1 1 d . . . H20 H -0.2052 0.6086 0.2648 0.069 Uiso 1 1 calc R . . C21 C -0.1564(10) 0.8216(6) 0.28636(16) 0.0570(14) Uani 1 1 d . . . H21 H -0.2932 0.8381 0.3044 0.068 Uiso 1 1 calc R . . C22 C 0.3592(10) 0.4088(6) 0.22117(18) 0.0572(14) Uani 1 1 d . . . C23 C 0.4273(9) 0.2678(6) 0.19518(16) 0.0542(13) Uani 1 1 d . . . C24 C 0.6299(10) 0.1588(6) 0.20472(18) 0.0647(15) Uani 1 1 d . . . H24 H 0.7213 0.1756 0.2274 0.078 Uiso 1 1 calc R . . C25 C 0.6987(10) 0.0227(7) 0.18035(18) 0.0677(16) Uani 1 1 d . . . H25 H 0.8345 -0.0523 0.1872 0.081 Uiso 1 1 calc R . . C26 C 0.5688(9) -0.0016(7) 0.14666(18) 0.0626(15) Uani 1 1 d . . . H26 H 0.6181 -0.0933 0.1309 0.075 Uiso 1 1 calc R . . C27 C 0.3626(9) 0.1080(7) 0.13507(17) 0.0601(15) Uani 1 1 d . . . C28 C 0.2881(9) 0.2457(6) 0.16133(16) 0.0504(13) Uani 1 1 d . . . C29 C 0.2183(10) 0.0977(7) 0.09994(18) 0.0661(16) Uani 1 1 d . . . C30 C 0.0100(10) 0.2029(8) 0.09262(18) 0.0750(18) Uani 1 1 d . . . H30 H -0.0853 0.1874 0.0704 0.09 Uiso 1 1 calc R . . C31 C -0.0593(10) 0.3360(7) 0.11923(19) 0.0731(17) Uani 1 1 d . . . H31 H -0.199 0.4098 0.1141 0.088 Uiso 1 1 calc R . . C32 C 0.0765(9) 0.3564(6) 0.15209(15) 0.0536(13) Uani 1 1 d . . . C33 C 0.0015(10) 0.5032(7) 0.17789(17) 0.0587(14) Uani 1 1 d . . . N1 N 0.1508(7) 0.5207(5) 0.21048(13) 0.0500(11) Uani 1 1 d . . . O1 O -0.5033(6) 2.0402(4) 0.42706(12) 0.0665(11) Uani 1 1 d . . . O2 O 0.4746(8) 0.4316(5) 0.25091(14) 0.0852(13) Uani 1 1 d . . . O3 O -0.1756(7) 0.6051(5) 0.17111(13) 0.0786(12) Uani 1 1 d . . . C34 C 0.3019(12) -0.0311(9) 0.0657(2) 0.0813(19) Uani 1 1 d . A . F1 F 0.1969(7) 0.0173(5) 0.02844(11) 0.1040(13) Uani 1 1 d . . . F2 F 0.5399(7) -0.0490(5) 0.05658(11) 0.0888(11) Uani 1 1 d . . . C35 C 0.2428(12) -0.1972(9) 0.0778(2) 0.086(2) Uani 1 1 d D . . F3 F 0.013(2) -0.196(4) 0.0864(10) 0.140(10) Uani 0.5 1 d PD A 1 F4 F 0.355(5) -0.268(3) 0.1125(6) 0.144(11) Uani 0.5 1 d PD A 1 F3A F 0.303(4) -0.239(3) 0.1175(5) 0.090(5) Uani 0.5 1 d PD A 2 F4A F 0.001(2) -0.165(4) 0.0753(10) 0.133(10) Uani 0.5 1 d PD A 2 C36 C 0.3386(18) -0.3295(11) 0.0455(3) 0.112(3) Uani 1 1 d D A . F5 F 0.337(4) -0.277(3) 0.0052(5) 0.162(9) Uani 0.5 1 d PD A 1 F6 F 0.569(2) -0.375(3) 0.0540(6) 0.140(7) Uani 0.5 1 d PD A 1 F7 F 0.232(5) -0.449(3) 0.0511(10) 0.235(18) Uani 0.5 1 d PD A 1 F5A F 0.207(5) -0.296(3) 0.0114(6) 0.202(13) Uani 0.5 1 d PD A 2 F6A F 0.558(3) -0.343(3) 0.0330(8) 0.192(14) Uani 0.5 1 d PD A 2 F7A F 0.296(4) -0.4701(15) 0.0609(7) 0.116(6) Uani 0.5 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.061(4) 0.044(3) 0.057(3) -0.004(3) -0.006(3) -0.003(3) C2 0.058(3) 0.050(3) 0.054(3) -0.006(3) -0.012(3) -0.012(3) C3 0.047(3) 0.059(4) 0.056(3) -0.002(3) -0.013(2) -0.004(3) C4 0.051(3) 0.052(3) 0.062(3) -0.001(3) -0.008(3) 0.003(3) C5 0.052(3) 0.046(3) 0.061(3) -0.011(3) -0.005(3) 0.002(3) C6 0.051(3) 0.050(3) 0.060(3) -0.008(3) -0.012(3) -0.002(3) C7 0.052(3) 0.050(3) 0.067(3) -0.004(3) -0.019(3) -0.005(3) C8 0.052(3) 0.049(3) 0.074(4) -0.009(3) -0.011(3) 0.000(3) C9 0.047(3) 0.047(3) 0.046(3) 0.002(2) -0.006(2) -0.006(2) C10 0.047(3) 0.040(3) 0.051(3) -0.001(2) -0.006(2) -0.003(2) C11 0.059(3) 0.054(3) 0.072(4) -0.014(3) -0.012(3) -0.002(3) C12 0.070(4) 0.050(3) 0.070(4) -0.009(3) -0.003(3) -0.009(3) C13 0.093(5) 0.071(4) 0.079(4) -0.017(3) -0.018(4) -0.014(4) C14 0.062(4) 0.053(4) 0.058(3) -0.006(3) -0.008(3) -0.005(3) C15 0.059(4) 0.055(4) 0.062(3) -0.008(3) -0.014(3) -0.001(3) C16 0.056(3) 0.044(3) 0.057(3) -0.007(3) -0.010(3) 0.003(3) C17 0.050(3) 0.055(3) 0.072(4) -0.004(3) -0.007(3) -0.008(3) C18 0.056(3) 0.060(4) 0.063(4) -0.008(3) 0.000(3) -0.004(3) C19 0.052(3) 0.040(3) 0.052(3) -0.006(2) -0.008(3) 0.006(3) C20 0.057(3) 0.046(3) 0.069(4) -0.009(3) -0.003(3) -0.011(3) C21 0.054(3) 0.057(4) 0.058(3) -0.006(3) -0.001(3) -0.004(3) C22 0.063(4) 0.047(3) 0.059(3) -0.004(3) -0.011(3) 0.001(3) C23 0.057(3) 0.047(3) 0.055(3) -0.001(3) -0.008(3) 0.000(3) C24 0.064(4) 0.051(3) 0.073(4) -0.004(3) -0.018(3) 0.008(3) C25 0.064(4) 0.058(4) 0.075(4) -0.005(3) -0.020(3) 0.008(3) C26 0.055(3) 0.060(4) 0.068(4) -0.017(3) -0.012(3) 0.008(3) C27 0.052(3) 0.065(4) 0.062(3) -0.011(3) -0.002(3) -0.004(3) C28 0.049(3) 0.045(3) 0.052(3) -0.001(2) -0.001(2) 0.005(2) C29 0.061(4) 0.069(4) 0.066(4) -0.017(3) -0.016(3) 0.001(3) C30 0.063(4) 0.091(5) 0.065(4) -0.020(3) -0.017(3) 0.012(3) C31 0.059(4) 0.078(4) 0.076(4) -0.011(3) -0.018(3) 0.009(3) C32 0.056(3) 0.059(3) 0.046(3) -0.008(3) -0.009(3) -0.009(3) C33 0.061(4) 0.057(4) 0.056(3) -0.006(3) -0.008(3) -0.002(3) N1 0.049(2) 0.041(2) 0.056(3) -0.008(2) -0.010(2) 0.0063(19) O1 0.060(2) 0.052(2) 0.085(3) -0.017(2) -0.015(2) 0.0029(18) O2 0.092(3) 0.073(3) 0.085(3) -0.010(2) -0.041(3) 0.011(2) O3 0.069(3) 0.077(3) 0.082(3) -0.015(2) -0.028(2) 0.016(2) C34 0.070(5) 0.096(5) 0.075(4) -0.011(4) -0.019(4) -0.002(4) F1 0.125(3) 0.118(3) 0.063(2) -0.021(2) -0.026(2) 0.006(2) F2 0.077(3) 0.107(3) 0.080(2) -0.027(2) 0.0175(19) -0.012(2) C35 0.080(5) 0.089(5) 0.089(5) -0.025(4) -0.010(5) -0.012(4) F3 0.079(12) 0.088(9) 0.25(2) -0.043(12) 0.076(12) -0.010(7) F4 0.23(2) 0.116(13) 0.086(12) -0.024(9) -0.054(14) -0.018(11) F3A 0.142(11) 0.084(9) 0.059(8) -0.015(6) 0.015(7) -0.059(9) F4A 0.075(11) 0.15(2) 0.190(15) -0.053(13) -0.014(9) -0.041(9) C36 0.117(9) 0.107(8) 0.109(8) -0.054(7) -0.011(7) 0.002(7) F5 0.23(2) 0.136(17) 0.106(11) -0.079(10) -0.026(11) 0.016(14) F6 0.107(12) 0.131(11) 0.153(15) -0.008(9) 0.026(8) 0.048(9) F7 0.23(2) 0.25(3) 0.26(3) -0.18(3) 0.04(2) -0.10(2) F5A 0.41(4) 0.104(11) 0.111(12) -0.017(10) -0.112(18) -0.06(2) F6A 0.21(2) 0.128(16) 0.24(3) -0.105(19) 0.13(2) -0.056(15) F7A 0.174(14) 0.049(7) 0.124(10) -0.026(7) 0.010(9) -0.020(7) #----------------------------------------------------------------------------# # 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 C1 C2 1.370(7) . ? C1 C8 1.407(7) . ? C1 C14 1.439(7) . ? C2 C9 1.406(7) . ? C2 H2 0.93 . ? C3 C4 1.359(7) . ? C3 C9 1.422(7) . ? C3 H3 0.93 . ? C4 C5 1.400(7) . ? C4 H4 0.93 . ? C5 C6 1.359(7) . ? C5 O1 1.373(6) . ? C6 C10 1.418(7) . ? C6 H6 0.93 . ? C7 C8 1.355(7) . ? C7 C10 1.415(6) . ? C7 H7 0.93 . ? C8 H8 0.93 . ? C9 C10 1.416(6) . ? C11 O1 1.427(6) . ? C11 C12 1.502(7) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 C13 1.512(7) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 H13A 0.96 . ? C13 H13B 0.96 . ? C13 H13C 0.96 . ? C14 C15 1.192(7) . ? C15 C16 1.432(7) . ? C16 C21 1.385(7) . ? C16 C17 1.386(7) . ? C17 C18 1.380(7) . ? C17 H17 0.93 . ? C18 C19 1.376(7) . ? C18 H18 0.93 . ? C19 C20 1.372(7) . ? C19 N1 1.439(6) . ? C20 C21 1.385(7) . ? C20 H20 0.93 . ? C21 H21 0.93 . ? C22 O2 1.208(6) . ? C22 N1 1.415(6) . ? C22 C23 1.456(7) . ? C23 C24 1.371(7) . ? C23 C28 1.393(7) . ? C24 C25 1.395(7) . ? C24 H24 0.93 . ? C25 C26 1.361(7) . ? C25 H25 0.93 . ? C26 C27 1.404(7) . ? C26 H26 0.93 . ? C27 C29 1.420(7) . ? C27 C28 1.443(7) . ? C28 C32 1.413(7) . ? C29 C30 1.364(7) . ? C29 C34 1.559(8) . ? C30 C31 1.417(8) . ? C30 H30 0.93 . ? C31 C32 1.352(7) . ? C31 H31 0.93 . ? C32 C33 1.496(7) . ? C33 O3 1.217(6) . ? C33 N1 1.390(6) . ? C34 F1 1.347(7) . ? C34 F2 1.349(7) . ? C34 C35 1.526(9) . ? C35 F3 1.318(15) . ? C35 F3A 1.322(14) . ? C35 F4 1.345(16) . ? C35 F4A 1.357(14) . ? C35 C36 1.548(10) . ? C36 F7 1.270(17) . ? C36 F6A 1.271(16) . ? C36 F5 1.314(17) . ? C36 F7A 1.318(14) . ? C36 F5A 1.323(16) . ? C36 F6 1.332(16) . ? 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 C2 C1 C8 119.0(5) . . ? C2 C1 C14 121.2(5) . . ? C8 C1 C14 119.7(5) . . ? C1 C2 C9 121.9(5) . . ? C1 C2 H2 119.1 . . ? C9 C2 H2 119.1 . . ? C4 C3 C9 121.0(5) . . ? C4 C3 H3 119.5 . . ? C9 C3 H3 119.5 . . ? C3 C4 C5 120.2(5) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 O1 124.9(5) . . ? C6 C5 C4 121.0(5) . . ? O1 C5 C4 114.1(4) . . ? C5 C6 C10 120.1(5) . . ? C5 C6 H6 119.9 . . ? C10 C6 H6 119.9 . . ? C8 C7 C10 121.9(5) . . ? C8 C7 H7 119 . . ? C10 C7 H7 119 . . ? C7 C8 C1 120.4(5) . . ? C7 C8 H8 119.8 . . ? C1 C8 H8 119.8 . . ? C2 C9 C10 118.9(4) . . ? C2 C9 C3 122.8(5) . . ? C10 C9 C3 118.2(5) . . ? C7 C10 C9 117.9(4) . . ? C7 C10 C6 122.7(5) . . ? C9 C10 C6 119.4(4) . . ? O1 C11 C12 108.5(4) . . ? O1 C11 H11A 110 . . ? C12 C11 H11A 110 . . ? O1 C11 H11B 110 . . ? C12 C11 H11B 110 . . ? H11A C11 H11B 108.4 . . ? C11 C12 C13 110.7(5) . . ? C11 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C1 177.9(6) . . ? C14 C15 C16 179.6(7) . . ? C21 C16 C17 118.4(5) . . ? C21 C16 C15 120.6(5) . . ? C17 C16 C15 121.1(5) . . ? C18 C17 C16 121.4(5) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C19 C18 C17 118.8(5) . . ? C19 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? C20 C19 C18 121.4(5) . . ? C20 C19 N1 120.0(5) . . ? C18 C19 N1 118.7(5) . . ? C19 C20 C21 119.2(5) . . ? C19 C20 H20 120.4 . . ? C21 C20 H20 120.4 . . ? C16 C21 C20 120.9(5) . . ? C16 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? O2 C22 N1 120.2(5) . . ? O2 C22 C23 122.1(5) . . ? N1 C22 C23 117.7(5) . . ? C24 C23 C28 121.2(5) . . ? C24 C23 C22 118.6(5) . . ? C28 C23 C22 120.2(5) . . ? C23 C24 C25 119.7(5) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C26 C25 C24 120.6(5) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C27 121.8(5) . . ? C25 C26 H26 119.1 . . ? C27 C26 H26 119.1 . . ? C26 C27 C29 126.6(5) . . ? C26 C27 C28 117.2(5) . . ? C29 C27 C28 116.2(5) . . ? C23 C28 C32 121.1(5) . . ? C23 C28 C27 119.4(4) . . ? C32 C28 C27 119.5(5) . . ? C30 C29 C27 123.1(5) . . ? C30 C29 C34 116.3(5) . . ? C27 C29 C34 120.5(5) . . ? C29 C30 C31 119.2(5) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.4 . . ? C32 C31 C30 120.4(5) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C31 C32 C28 121.5(5) . . ? C31 C32 C33 118.2(5) . . ? C28 C32 C33 120.2(5) . . ? O3 C33 N1 120.4(5) . . ? O3 C33 C32 123.7(5) . . ? N1 C33 C32 115.9(5) . . ? C33 N1 C22 124.8(4) . . ? C33 N1 C19 119.2(4) . . ? C22 N1 C19 116.0(4) . . ? C5 O1 C11 117.8(4) . . ? F1 C34 F2 105.5(5) . . ? F1 C34 C35 106.6(6) . . ? F2 C34 C35 108.1(5) . . ? F1 C34 C29 110.2(5) . . ? F2 C34 C29 111.5(5) . . ? C35 C34 C29 114.4(6) . . ? F3 C35 F3A 93.7(19) . . ? F3 C35 F4 105.3(18) . . ? F3A C35 F4 16(2) . . ? F3 C35 F4A 18(3) . . ? F3A C35 F4A 110.4(16) . . ? F4 C35 F4A 123(2) . . ? F3 C35 C34 113.8(14) . . ? F3A C35 C34 109.7(10) . . ? F4 C35 C34 113.4(13) . . ? F4A C35 C34 100.3(14) . . ? F3 C35 C36 109.1(12) . . ? F3A C35 C36 113.5(13) . . ? F4 C35 C36 98.6(14) . . ? F4A C35 C36 106.9(12) . . ? C34 C35 C36 115.2(7) . . ? F7 C36 F6A 123(2) . . ? F7 C36 F5 111.2(13) . . ? F6A C36 F5 74.4(15) . . ? F7 C36 F7A 21.5(19) . . ? F6A C36 F7A 109.7(12) . . ? F5 C36 F7A 127.1(18) . . ? F7 C36 F5A 84.3(18) . . ? F6A C36 F5A 108.0(14) . . ? F5 C36 F5A 35.1(16) . . ? F7A C36 F5A 105.0(13) . . ? F7 C36 F6 109.7(14) . . ? F6A C36 F6 31.0(15) . . ? F5 C36 F6 105.4(14) . . ? F7A C36 F6 90.0(15) . . ? F5A C36 F6 138.0(17) . . ? F7 C36 C35 111.4(18) . . ? F6A C36 C35 116.8(13) . . ? F5 C36 C35 114.3(13) . . ? F7A C36 C35 109.8(11) . . ? F5A C36 C35 106.8(14) . . ? F6 C36 C35 104.3(11) . . ? # Attachment 'Molecule2.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-10-14 at 11:04:18 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : struct import dreduc data_struct_615873 _database_code_depnum_ccdc_archive 'CCDC 615873' _audit_creation_date 2006-10-14T11:04:18-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C42 H28 F13 N1 O3' _chemical_formula_weight 841.65 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8313(3) _cell_length_b 8.9482(5) _cell_length_c 36.8720(19) _cell_angle_alpha 90.655(2) _cell_angle_beta 91.406(2) _cell_angle_gamma 104.355(2) _cell_volume 1863.03(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293 _cell_measurement_reflns_used 2862 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.5 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.152599 _diffrn_orient_matrix_ub_12 -0.6788E-2 _diffrn_orient_matrix_ub_13 -0.13668E-1 _diffrn_orient_matrix_ub_21 -0.07862 _diffrn_orient_matrix_ub_22 0.120189E-1 _diffrn_orient_matrix_ub_23 0.232766E-1 _diffrn_orient_matrix_ub_31 0.434936E-1 _diffrn_orient_matrix_ub_32 0.114546 _diffrn_orient_matrix_ub_33 -0.2758E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0637 _diffrn_reflns_number 6363 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.23 _diffrn_reflns_theta_full 25.23 _diffrn_measured_fraction_theta_full 0.949 _diffrn_measured_fraction_theta_max 0.949 _reflns_number_total 6363 _reflns_number_gt 3251 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; 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. The carbon-carbon bond lengths in the fluorocarbon chain were restrained using DFIX command with a distance of 1.55 A (0.02 as standard deviation). The C-F bond length was restrained at a distance of 1.35 A using DFIX with 0.02 as standard deviation. The distance between the geminal fluorines were restrained using DANG 2.20 with 0.04 as standard deviation. In the anisotropic refinement, F9, F9A, F10, F10A F11, F12 F13, F11A, F12A and F13A atoms were restrained using SIMU command with 0.05 as standard deviation. The fluorine atoms on C41 and and C42 as disorder over two sites. C42 was also modeled as disordered over two sites with equal occupancy. We did not model the disorder on other fluorine and carbon atoms of the fluorocarbon chain due to lack of good quality data. Attempts to model disorder on these sites resulted in models with unreasonable bond lengths and angles. The refinements did not converge if disorders were introduced at these sites. ; _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^)+(0.0883P)^2^+3.5767P] 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 noref _refine_ls_extinction_method none _refine_ls_number_reflns 6363 _refine_ls_number_parameters 586 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.1775 _refine_ls_R_factor_gt 0.1008 _refine_ls_wR_factor_ref 0.2773 _refine_ls_wR_factor_gt 0.2332 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.372 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.072 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_number_in_cell C 84 H 56 F 26 N 2 O 6 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 C1 C 0.5913(9) 0.7574(5) 0.16235(13) 0.0536(12) Uani 1 1 d . . . H1 H 0.4717 0.779 0.1762 0.064 Uiso 1 1 calc R . . C2 C 0.8005(9) 0.8690(5) 0.15907(14) 0.0562(13) Uani 1 1 d . . . C3 C 0.9794(9) 0.8359(6) 0.13733(15) 0.0647(15) Uani 1 1 d . . . H3 H 1.1201 0.9106 0.1345 0.078 Uiso 1 1 calc R . . C4 C 0.9471(9) 0.6962(6) 0.12065(15) 0.0636(14) Uani 1 1 d . . . H4 H 1.0664 0.6771 0.1064 0.076 Uiso 1 1 calc R . . C5 C 0.7036(9) 0.4294(5) 0.10853(14) 0.0583(13) Uani 1 1 d . . . H5 H 0.8225 0.4066 0.0948 0.07 Uiso 1 1 calc R . . C6 C 0.4964(9) 0.3187(6) 0.11348(14) 0.0578(13) Uani 1 1 d . . . C7 C 0.3148(9) 0.3526(6) 0.13410(14) 0.0598(14) Uani 1 1 d . . . H7 H 0.1744 0.2777 0.137 0.072 Uiso 1 1 calc R . . C8 C 0.3442(9) 0.4941(6) 0.14970(14) 0.0599(14) Uani 1 1 d . . . H8 H 0.2241 0.5146 0.1636 0.072 Uiso 1 1 calc R . . C9 C 0.5549(8) 0.6118(5) 0.14526(13) 0.0509(12) Uani 1 1 d . . . C10 C 0.7350(8) 0.5775(5) 0.12437(13) 0.0503(12) Uani 1 1 d . . . C11 C 0.6219(10) 0.1251(6) 0.07912(16) 0.0704(16) Uani 1 1 d . . . H11A H 0.765 0.1337 0.0938 0.084 Uiso 1 1 calc R . . H11B H 0.6609 0.191 0.0583 0.084 Uiso 1 1 calc R . . C12 C 0.5220(11) -0.0401(6) 0.06676(17) 0.0771(17) Uani 1 1 d . . . H12A H 0.374 -0.048 0.0534 0.093 Uiso 1 1 calc R . . H12B H 0.4882 -0.1049 0.0879 0.093 Uiso 1 1 calc R . . C13 C 0.6903(12) -0.0988(7) 0.04290(19) 0.0876(19) Uani 1 1 d . . . H13A H 0.715 -0.0385 0.021 0.105 Uiso 1 1 calc R . . H13B H 0.8421 -0.0837 0.0556 0.105 Uiso 1 1 calc R . . C14 C 0.6000(14) -0.2669(8) 0.0326(2) 0.116(3) Uani 1 1 d . . . H14A H 0.4692 -0.2774 0.0152 0.139 Uiso 1 1 calc R . . H14B H 0.5384 -0.3231 0.054 0.139 Uiso 1 1 calc R . . C15 C 0.791(2) -0.3447(11) 0.0157(3) 0.149(4) Uani 1 1 d . . . H15A H 0.9401 -0.3118 0.0293 0.178 Uiso 1 1 calc R . . H15B H 0.7375 -0.4561 0.0169 0.178 Uiso 1 1 calc R . . C16 C 0.822(2) -0.3019(13) -0.0192(3) 0.175(5) Uani 1 1 d . . . H16A H 0.9291 -0.3536 -0.0302 0.263 Uiso 1 1 calc R . . H16B H 0.8854 -0.1924 -0.0202 0.263 Uiso 1 1 calc R . . H16C H 0.6718 -0.3295 -0.0322 0.263 Uiso 1 1 calc R . . C17 C 0.8378(9) 1.0158(6) 0.17782(14) 0.0595(13) Uani 1 1 d . . . C18 C 0.8731(9) 1.1363(6) 0.19394(14) 0.0586(13) Uani 1 1 d . . . C19 C 0.9201(9) 1.2791(5) 0.21391(13) 0.0537(13) Uani 1 1 d . . . C20 C 0.7744(9) 1.3798(5) 0.21031(14) 0.0590(13) Uani 1 1 d . . . H20 H 0.6437 1.3547 0.1944 0.071 Uiso 1 1 calc R . . C21 C 0.8212(9) 1.5166(5) 0.22999(14) 0.0593(14) Uani 1 1 d . . . H21 H 0.7226 1.5833 0.2273 0.071 Uiso 1 1 calc R . . C22 C 1.0144(9) 1.5542(5) 0.25362(13) 0.0532(13) Uani 1 1 d . . . C23 C 1.1616(9) 1.4566(5) 0.25758(14) 0.0577(13) Uani 1 1 d . . . H23 H 1.2919 1.4824 0.2735 0.069 Uiso 1 1 calc R . . C24 C 1.1151(9) 1.3205(6) 0.23783(15) 0.0611(14) Uani 1 1 d . . . H24 H 1.2155 1.255 0.2405 0.073 Uiso 1 1 calc R . . C25 C 0.9586(9) 1.8689(5) 0.31976(14) 0.0563(13) Uani 1 1 d . . . C26 C 0.8083(10) 1.8964(7) 0.34522(16) 0.0737(16) Uani 1 1 d . . . H26 H 0.6754 1.8192 0.3507 0.088 Uiso 1 1 calc R . . C27 C 0.8514(10) 2.0400(7) 0.36328(17) 0.0828(19) Uani 1 1 d . . . H27 H 0.7466 2.0575 0.3805 0.099 Uiso 1 1 calc R . . C28 C 1.0465(11) 2.1540(7) 0.35566(17) 0.0786(18) Uani 1 1 d . . . C29 C 1.4265(9) 2.2409(6) 0.32161(15) 0.0640(15) Uani 1 1 d . . . H29 H 1.4634 2.3369 0.3333 0.077 Uiso 1 1 calc R . . C30 C 1.5751(10) 2.2100(6) 0.29642(15) 0.0661(15) Uani 1 1 d . . . H30 H 1.713 2.2841 0.2914 0.079 Uiso 1 1 calc R . . C31 C 1.5232(9) 2.0684(6) 0.27797(14) 0.0642(15) Uani 1 1 d . . . H31 H 1.625 2.049 0.2605 0.077 Uiso 1 1 calc R . . C32 C 1.3220(9) 1.9573(5) 0.28554(13) 0.0536(13) Uani 1 1 d . . . C33 C 1.1663(8) 1.9854(5) 0.31158(13) 0.0516(12) Uani 1 1 d . . . C34 C 1.2170(9) 2.1310(6) 0.33058(14) 0.0611(14) Uani 1 1 d . . . C35 C 1.2725(10) 1.8097(6) 0.26566(14) 0.0617(14) Uani 1 1 d . . . C36 C 0.9038(9) 1.7184(6) 0.30011(14) 0.0586(13) Uani 1 1 d . . . C37 C 1.0681(12) 2.3168(10) 0.3738(2) 0.105(2) Uani 1 1 d D . . C38 C 1.2088(15) 2.3338(9) 0.4082(2) 0.114(3) Uani 1 1 d D . . C39 C 1.306(2) 2.4991(11) 0.4257(3) 0.196(6) Uani 1 1 d D . . C40 C 1.168(2) 2.6068(10) 0.4316(3) 0.163(5) Uani 1 1 d D A . C41 C 1.268(3) 2.7530(14) 0.4569(4) 0.186(6) Uani 1 1 d D . . F1 F 1.1585(8) 2.4370(4) 0.35140(12) 0.1071(13) Uani 1 1 d D . . F2 F 0.8491(7) 2.3384(5) 0.38150(14) 0.1329(17) Uani 1 1 d D . . F3 F 1.0796(9) 2.2357(6) 0.43092(13) 0.1358(17) Uani 1 1 d D . . F4 F 1.4063(8) 2.2916(6) 0.40320(11) 0.1255(16) Uani 1 1 d D . . F5 F 1.3937(14) 2.4796(7) 0.45879(17) 0.197(3) Uani 1 1 d D . . F6 F 1.4701(11) 2.5977(9) 0.40251(19) 0.204(3) Uani 1 1 d D . . F7 F 0.9653(12) 2.5067(9) 0.4495(2) 0.208(3) Uani 1 1 d D . . F8 F 1.0647(13) 2.6411(7) 0.40005(19) 0.188(3) Uani 1 1 d D . . F9 F 1.177(8) 2.726(3) 0.4913(7) 0.316(18) Uani 0.5 1 d PDU A 1 F10 F 1.510(3) 2.785(2) 0.4595(10) 0.191(9) Uani 0.5 1 d PDU A 1 C42 C 1.214(4) 2.9043(16) 0.4439(6) 0.30(4) Uani 0.5 1 d PD A 1 F11 F 1.353(4) 2.911(3) 0.4163(5) 0.215(8) Uani 0.5 1 d PD A 1 F12 F 0.988(4) 2.838(4) 0.4490(12) 0.243(16) Uani 0.5 1 d PDU A 1 F13 F 1.293(6) 2.996(3) 0.4722(8) 0.258(16) Uani 0.5 1 d PDU A 1 F9A F 1.354(6) 2.716(2) 0.4896(5) 0.206(11) Uani 0.5 1 d PDU A 2 F10A F 1.443(6) 2.848(4) 0.4387(7) 0.275(19) Uani 0.5 1 d PDU A 2 C42A C 1.099(4) 2.853(3) 0.4675(7) 0.25(4) Uani 0.5 1 d PD A 2 F11A F 1.023(6) 2.890(3) 0.4357(7) 0.205(14) Uani 0.5 1 d PDU A 2 F12A F 0.949(5) 2.758(3) 0.4874(7) 0.253(11) Uani 0.5 1 d PDU A 2 F13A F 1.237(5) 2.962(3) 0.4873(9) 0.266(18) Uani 0.5 1 d PDU A 2 N1 N 1.0629(7) 1.6981(4) 0.27400(11) 0.0544(11) Uani 1 1 d . . . O1 O 0.4464(6) 0.1708(4) 0.09988(10) 0.0714(11) Uani 1 1 d . . . O2 O 0.7328(7) 1.6139(4) 0.30677(11) 0.0777(12) Uani 1 1 d . . . O3 O 1.4041(8) 1.7799(4) 0.24332(12) 0.0938(15) Uani 1 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 C1 0.056(3) 0.050(3) 0.056(3) -0.004(2) 0.008(2) 0.015(2) C2 0.065(3) 0.042(3) 0.060(3) -0.004(2) 0.005(3) 0.009(2) C3 0.060(3) 0.046(3) 0.081(4) -0.011(3) 0.008(3) -0.001(2) C4 0.057(3) 0.054(3) 0.078(4) -0.009(3) 0.016(3) 0.011(3) C5 0.060(3) 0.049(3) 0.063(3) -0.011(2) 0.010(3) 0.008(2) C6 0.065(3) 0.046(3) 0.058(3) -0.010(2) 0.000(3) 0.006(3) C7 0.055(3) 0.054(3) 0.063(3) -0.007(3) 0.005(3) 0.000(2) C8 0.054(3) 0.058(3) 0.066(3) -0.006(3) 0.011(3) 0.012(3) C9 0.055(3) 0.044(3) 0.052(3) -0.004(2) 0.004(2) 0.008(2) C10 0.052(3) 0.045(3) 0.052(3) -0.003(2) 0.006(2) 0.008(2) C11 0.079(4) 0.055(3) 0.074(4) -0.018(3) 0.009(3) 0.012(3) C12 0.091(4) 0.053(3) 0.083(4) -0.018(3) -0.001(3) 0.010(3) C13 0.097(5) 0.073(4) 0.094(5) -0.027(3) 0.005(4) 0.024(4) C14 0.129(6) 0.086(5) 0.135(7) -0.054(5) 0.008(5) 0.035(5) C15 0.193(10) 0.106(7) 0.148(9) -0.036(6) -0.017(8) 0.042(7) C16 0.205(11) 0.187(11) 0.136(9) 0.046(8) 0.051(8) 0.046(9) C17 0.068(3) 0.050(3) 0.058(3) -0.005(3) 0.005(3) 0.012(3) C18 0.063(3) 0.046(3) 0.062(3) -0.006(3) 0.011(3) 0.004(2) C19 0.059(3) 0.041(3) 0.056(3) -0.004(2) 0.008(3) 0.003(2) C20 0.062(3) 0.051(3) 0.060(3) -0.005(3) -0.006(3) 0.008(3) C21 0.069(4) 0.043(3) 0.067(3) -0.003(3) 0.003(3) 0.017(3) C22 0.059(3) 0.037(3) 0.058(3) -0.002(2) 0.007(3) 0.000(2) C23 0.055(3) 0.051(3) 0.064(3) -0.010(3) 0.001(3) 0.008(3) C24 0.060(3) 0.049(3) 0.076(4) -0.003(3) 0.007(3) 0.015(2) C25 0.056(3) 0.052(3) 0.057(3) -0.005(2) 0.005(3) 0.006(2) C26 0.056(3) 0.075(4) 0.082(4) -0.010(3) 0.018(3) 0.001(3) C27 0.066(4) 0.082(4) 0.089(4) -0.034(4) 0.020(3) -0.003(3) C28 0.072(4) 0.074(4) 0.084(4) -0.031(3) 0.009(3) 0.008(3) C29 0.065(3) 0.050(3) 0.070(4) -0.015(3) 0.006(3) 0.001(3) C30 0.062(3) 0.054(3) 0.073(4) -0.004(3) 0.013(3) -0.005(3) C31 0.069(3) 0.052(3) 0.065(3) -0.003(3) 0.019(3) 0.002(3) C32 0.061(3) 0.040(3) 0.055(3) -0.001(2) 0.011(3) 0.003(2) C33 0.055(3) 0.043(3) 0.053(3) -0.003(2) 0.001(2) 0.004(2) C34 0.056(3) 0.057(3) 0.065(3) -0.013(3) 0.008(3) 0.005(3) C35 0.073(4) 0.046(3) 0.061(3) -0.005(2) 0.017(3) 0.003(3) C36 0.059(3) 0.053(3) 0.060(3) -0.005(3) 0.006(3) 0.008(3) C37 0.070(5) 0.132(7) 0.105(6) -0.030(5) 0.021(4) 0.012(4) C38 0.096(6) 0.147(8) 0.092(6) -0.021(5) 0.020(5) 0.014(5) C39 0.292(17) 0.119(8) 0.177(12) -0.103(9) -0.085(12) 0.062(10) C40 0.171(11) 0.130(8) 0.171(11) -0.086(8) 0.022(9) 0.009(8) C41 0.207(16) 0.130(11) 0.220(18) -0.096(12) 0.009(13) 0.043(11) F1 0.145(4) 0.075(2) 0.109(3) -0.013(2) 0.003(3) 0.043(2) F2 0.084(3) 0.153(4) 0.170(4) -0.070(3) -0.007(3) 0.047(3) F3 0.138(4) 0.143(4) 0.112(3) -0.004(3) 0.035(3) 0.005(3) F4 0.087(3) 0.195(5) 0.096(3) -0.041(3) -0.013(2) 0.042(3) F5 0.289(8) 0.166(5) 0.119(4) -0.057(4) -0.068(5) 0.037(5) F6 0.148(5) 0.223(7) 0.185(6) 0.003(5) 0.049(4) -0.067(5) F7 0.148(5) 0.251(7) 0.215(7) -0.028(6) 0.080(5) 0.027(5) F8 0.241(7) 0.162(5) 0.175(6) -0.094(5) -0.079(5) 0.092(5) F9 0.52(5) 0.27(2) 0.23(2) -0.004(18) 0.19(3) 0.20(3) F10 0.140(11) 0.160(14) 0.26(2) -0.121(16) -0.023(14) 0.016(11) C42 0.098(19) 0.18(3) 0.61(12) -0.25(6) 0.01(4) 0.02(2) F11 0.206(18) 0.218(18) 0.186(17) 0.017(13) 0.081(14) -0.018(14) F12 0.24(2) 0.24(3) 0.28(3) -0.11(3) 0.05(3) 0.12(2) F13 0.39(4) 0.095(9) 0.28(3) -0.105(14) -0.16(2) 0.067(14) F9A 0.31(3) 0.217(16) 0.144(14) -0.106(14) -0.103(18) 0.182(19) F10A 0.32(4) 0.26(3) 0.20(3) 0.04(2) -0.02(2) -0.02(2) C42A 0.40(10) 0.17(4) 0.19(5) -0.04(4) -0.09(6) 0.12(6) F11A 0.27(3) 0.159(15) 0.19(2) -0.030(12) -0.101(19) 0.075(15) F12A 0.35(3) 0.22(2) 0.21(2) 0.000(15) 0.10(2) 0.11(2) F13A 0.28(2) 0.27(3) 0.28(3) -0.22(3) -0.068(19) 0.14(2) N1 0.062(3) 0.038(2) 0.058(3) -0.0066(18) 0.009(2) 0.0004(19) O1 0.077(2) 0.049(2) 0.081(3) -0.0203(19) 0.011(2) 0.0017(18) O2 0.069(2) 0.063(2) 0.088(3) -0.013(2) 0.022(2) -0.009(2) O3 0.108(3) 0.062(2) 0.098(3) -0.017(2) 0.053(3) -0.008(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 C1 C2 1.381(6) . ? C1 C9 1.406(6) . ? C1 H1 0.93 . ? C2 C3 1.417(7) . ? C2 C17 1.442(7) . ? C3 C4 1.355(7) . ? C3 H3 0.93 . ? C4 C10 1.427(6) . ? C4 H4 0.93 . ? C5 C6 1.377(7) . ? C5 C10 1.410(6) . ? C5 H5 0.93 . ? C6 O1 1.369(5) . ? C6 C7 1.409(7) . ? C7 C8 1.354(7) . ? C7 H7 0.93 . ? C8 C9 1.420(6) . ? C8 H8 0.93 . ? C9 C10 1.409(6) . ? C11 O1 1.428(6) . ? C11 C12 1.509(7) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 C13 1.516(8) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.506(8) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 C15 1.589(11) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C15 C16 1.352(12) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C17 C18 1.195(6) . ? C18 C19 1.430(7) . ? C19 C20 1.389(7) . ? C19 C24 1.394(7) . ? C20 C21 1.380(7) . ? C20 H20 0.93 . ? C21 C22 1.378(7) . ? C21 H21 0.93 . ? C22 C23 1.375(7) . ? C22 N1 1.446(6) . ? C23 C24 1.375(7) . ? C23 H23 0.93 . ? C24 H24 0.93 . ? C25 C26 1.361(7) . ? C25 C33 1.430(6) . ? C25 C36 1.481(7) . ? C26 C27 1.404(7) . ? C26 H26 0.93 . ? C27 C28 1.364(8) . ? C27 H27 0.93 . ? C28 C34 1.424(7) . ? C28 C37 1.570(9) . ? C29 C30 1.358(7) . ? C29 C34 1.414(7) . ? C29 H29 0.93 . ? C30 C31 1.393(7) . ? C30 H30 0.93 . ? C31 C32 1.374(6) . ? C31 H31 0.93 . ? C32 C33 1.400(6) . ? C32 C35 1.464(7) . ? C33 C34 1.433(6) . ? C35 O3 1.211(6) . ? C35 N1 1.417(6) . ? C36 O2 1.218(6) . ? C36 N1 1.394(6) . ? C37 F1 1.370(8) . ? C37 F2 1.374(7) . ? C37 C38 1.479(9) . ? C38 F4 1.314(8) . ? C38 F3 1.327(8) . ? C38 C39 1.571(9) . ? C39 F5 1.343(10) . ? C39 C40 1.418(12) . ? C39 F6 1.437(13) . ? C40 F8 1.370(11) . ? C40 F7 1.470(10) . ? C40 C41 1.577(11) . ? C41 F10A 1.354(19) . ? C41 F9A 1.369(15) . ? C41 F10 1.370(15) . ? C41 F9 1.385(17) . ? C41 C42A 1.540(11) . ? C41 C42 1.541(10) . ? C42 F11 1.309(18) . ? C42 F13 1.321(17) . ? C42 F12 1.324(19) . ? C42A F13A 1.303(19) . ? C42A F12A 1.306(19) . ? C42A F11A 1.317(19) . ? 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 C2 C1 C9 121.5(4) . . ? C2 C1 H1 119.3 . . ? C9 C1 H1 119.3 . . ? C1 C2 C3 118.8(4) . . ? C1 C2 C17 120.7(5) . . ? C3 C2 C17 120.6(5) . . ? C4 C3 C2 120.5(5) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C10 121.8(5) . . ? C3 C4 H4 119.1 . . ? C10 C4 H4 119.1 . . ? C6 C5 C10 119.8(5) . . ? C6 C5 H5 120.1 . . ? C10 C5 H5 120.1 . . ? O1 C6 C5 125.2(5) . . ? O1 C6 C7 114.3(4) . . ? C5 C6 C7 120.4(4) . . ? C8 C7 C6 120.2(5) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C9 121.3(5) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C1 C9 C10 119.8(4) . . ? C1 C9 C8 121.9(4) . . ? C10 C9 C8 118.3(4) . . ? C9 C10 C5 120.0(4) . . ? C9 C10 C4 117.6(4) . . ? C5 C10 C4 122.4(4) . . ? O1 C11 C12 107.8(4) . . ? O1 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? O1 C11 H11B 110.1 . . ? C12 C11 H11B 110.1 . . ? H11A C11 H11B 108.5 . . ? C11 C12 C13 112.3(5) . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12B 109.1 . . ? C13 C12 H12B 109.1 . . ? H12A C12 H12B 107.9 . . ? C14 C13 C12 112.8(5) . . ? C14 C13 H13A 109 . . ? C12 C13 H13A 109 . . ? C14 C13 H13B 109 . . ? C12 C13 H13B 109 . . ? H13A C13 H13B 107.8 . . ? C13 C14 C15 115.0(7) . . ? C13 C14 H14A 108.5 . . ? C15 C14 H14A 108.5 . . ? C13 C14 H14B 108.5 . . ? C15 C14 H14B 108.5 . . ? H14A C14 H14B 107.5 . . ? C16 C15 C14 108.7(9) . . ? C16 C15 H15A 109.9 . . ? C14 C15 H15A 109.9 . . ? C16 C15 H15B 109.9 . . ? C14 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C2 178.2(6) . . ? C17 C18 C19 178.4(6) . . ? C20 C19 C24 118.1(4) . . ? C20 C19 C18 121.6(5) . . ? C24 C19 C18 120.3(5) . . ? C21 C20 C19 120.8(5) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C22 C21 C20 119.8(5) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C23 C22 C21 120.4(4) . . ? C23 C22 N1 120.1(5) . . ? C21 C22 N1 119.5(5) . . ? C22 C23 C24 119.7(5) . . ? C22 C23 H23 120.2 . . ? C24 C23 H23 120.2 . . ? C23 C24 C19 121.2(5) . . ? C23 C24 H24 119.4 . . ? C19 C24 H24 119.4 . . ? C26 C25 C33 120.2(5) . . ? C26 C25 C36 119.6(5) . . ? C33 C25 C36 120.1(4) . . ? C25 C26 C27 120.8(5) . . ? C25 C26 H26 119.6 . . ? C27 C26 H26 119.6 . . ? C28 C27 C26 120.2(5) . . ? C28 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? C27 C28 C34 122.0(5) . . ? C27 C28 C37 117.1(5) . . ? C34 C28 C37 120.7(5) . . ? C30 C29 C34 121.8(5) . . ? C30 C29 H29 119.1 . . ? C34 C29 H29 119.1 . . ? C29 C30 C31 120.6(5) . . ? C29 C30 H30 119.7 . . ? C31 C30 H30 119.7 . . ? C32 C31 C30 120.1(5) . . ? C32 C31 H31 119.9 . . ? C30 C31 H31 119.9 . . ? C31 C32 C33 120.5(4) . . ? C31 C32 C35 118.8(5) . . ? C33 C32 C35 120.7(4) . . ? C32 C33 C25 120.4(4) . . ? C32 C33 C34 119.9(4) . . ? C25 C33 C34 119.7(4) . . ? C29 C34 C28 126.0(5) . . ? C29 C34 C33 117.1(5) . . ? C28 C34 C33 116.9(5) . . ? O3 C35 N1 119.9(4) . . ? O3 C35 C32 122.8(5) . . ? N1 C35 C32 117.3(4) . . ? O2 C36 N1 120.4(4) . . ? O2 C36 C25 122.6(5) . . ? N1 C36 C25 116.9(4) . . ? F1 C37 F2 102.7(7) . . ? F1 C37 C38 110.3(6) . . ? F2 C37 C38 107.7(6) . . ? F1 C37 C28 113.5(5) . . ? F2 C37 C28 111.2(5) . . ? C38 C37 C28 111.0(7) . . ? F4 C38 F3 107.9(7) . . ? F4 C38 C37 109.9(6) . . ? F3 C38 C37 105.9(7) . . ? F4 C38 C39 101.4(7) . . ? F3 C38 C39 112.3(7) . . ? C37 C38 C39 119.1(7) . . ? F5 C39 C40 104.0(9) . . ? F5 C39 F6 114.7(10) . . ? C40 C39 F6 95.0(9) . . ? F5 C39 C38 106.8(8) . . ? C40 C39 C38 124.8(9) . . ? F6 C39 C38 111.4(8) . . ? F8 C40 C39 111.7(8) . . ? F8 C40 F7 101.9(9) . . ? C39 C40 F7 99.6(9) . . ? F8 C40 C41 112.9(9) . . ? C39 C40 C41 120.1(10) . . ? F7 C40 C41 107.9(9) . . ? F10A C41 F9A 110(2) . . ? F10A C41 F10 46.6(15) . . ? F9A C41 F10 66.1(15) . . ? F10A C41 F9 142(2) . . ? F9A C41 F9 45.3(16) . . ? F10 C41 F9 109(2) . . ? F10A C41 C42A 105(2) . . ? F9A C41 C42A 103.8(16) . . ? F10 C41 C42A 129.8(15) . . ? F9 C41 C42A 65.7(19) . . ? F10A C41 C42 64(2) . . ? F9A C41 C42 130.9(12) . . ? F10 C41 C42 104.5(18) . . ? F9 C41 C42 107.1(17) . . ? C42A C41 C42 43.4(13) . . ? F10A C41 C40 106.7(17) . . ? F9A C41 C40 112.4(12) . . ? F10 C41 C40 110.2(11) . . ? F9 C41 C40 109.8(16) . . ? C42A C41 C40 118.4(15) . . ? C42 C41 C40 115.7(10) . . ? F11 C42 F13 118(2) . . ? F11 C42 F12 134(2) . . ? F13 C42 F12 108(2) . . ? F11 C42 C41 91.9(15) . . ? F13 C42 C41 100.7(17) . . ? F12 C42 C41 87(2) . . ? F13A C42A F12A 111(2) . . ? F13A C42A F11A 118(2) . . ? F12A C42A F11A 118(2) . . ? F13A C42A C41 102.2(16) . . ? F12A C42A C41 101.1(19) . . ? F11A C42A C41 102(2) . . ? C36 N1 C35 124.5(4) . . ? C36 N1 C22 118.9(4) . . ? C35 N1 C22 116.6(4) . . ? C6 O1 C11 118.3(4) . . ? # Attachment 'Molecule3.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-10-16 at 14:45:26 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : struct import dreduc data_struct_615874 _database_code_depnum_ccdc_archive 'CCDC 615874' _audit_creation_date 2006-10-16T14:45:26-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C38 H32 F13 N1 O5' _chemical_formula_weight 829.65 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9502(3) _cell_length_b 9.5259(4) _cell_length_c 49.289(2) _cell_angle_alpha 88.7490(10) _cell_angle_beta 90.2360(10) _cell_angle_gamma 87.669(2) _cell_volume 3728.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 4747 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 19.98 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.14 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.233216E-1 _diffrn_orient_matrix_ub_12 -0.102896 _diffrn_orient_matrix_ub_13 -0.24304E-2 _diffrn_orient_matrix_ub_21 -0.06872 _diffrn_orient_matrix_ub_22 0.42603E-2 _diffrn_orient_matrix_ub_23 -0.170585E-1 _diffrn_orient_matrix_ub_31 0.102867 _diffrn_orient_matrix_ub_32 0.209299E-1 _diffrn_orient_matrix_ub_33 -0.107202E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0451 _diffrn_reflns_number 6097 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 19.98 _diffrn_reflns_theta_full 19.98 _diffrn_measured_fraction_theta_full 0.877 _diffrn_measured_fraction_theta_max 0.877 _reflns_number_total 6097 _reflns_number_gt 4134 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; 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. The Fourier difference map indicated that the fluorine atoms were disordered. The C-F distances of the fluorocarbon chains were restrained to be at 1.35 A using the DFIX command with 0.02 as standard deviation. The geminal F-F distances were restrained at 2.200 A using DANG command with 0.04 standard deviation. The C-F distance on the terminal carbon (C38) of one of the fluorocarbon chain was restrained using DFIX 1.35 with a standard deviation of 0.005. The DANG command for the fluorine atoms on C38 had a standard deviation of 0.01. The carbon-carbon distances were restrained to be the same using SADI command with 0.02 as standard deviation. In anisotropic refinement, the carbons on the each fluorocarbon chain were restrained using SIMU command with 0.04 as standard deviation and ISOR default values. The fluorines were also restrained with SIMU command with 0.04 as standard deviation and with ISOR command. The following models were tried: (a)fluorine disorderd over two sites on carbons C71, C72, C73, C74, C75 and C76 and fluorines isotropic thermal factors (b) fluorines and carbons disorderd over two sites for carbons C71, C72, C73, C74, C75 and C76 and fluorines isotropic thermal factors. Both refinements were unstable, did not converge and led to chemically unreasonable bond distances and angles. Therefore, we have now modeled the fluorines as ordered but with large thermal ellipsoids. We believe that since the disorder is large and the data/parameter ratio is low, we cannot further refine the disorder. We have attempted to collect data at low temperature but it does not improve the quality of the data. The model presented here is consistent the general conclusions of the paper. ; _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^)+(0.2000P)^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 noref _refine_ls_extinction_method none _refine_ls_number_reflns 6097 _refine_ls_number_parameters 1024 _refine_ls_number_restraints 325 _refine_ls_R_factor_all 0.1479 _refine_ls_R_factor_gt 0.1089 _refine_ls_wR_factor_ref 0.3541 _refine_ls_wR_factor_gt 0.312 _refine_ls_goodness_of_fit_ref 1.439 _refine_ls_restrained_S_all 1.469 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.629 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.069 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_number_in_cell C 152 H 128 F 52 N 4 O 20 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 -0.0809(10) 0.1128(7) 0.23329(18) 0.078(2) Uani 1 1 d . . . O1 O 0.4959(6) 1.0683(6) 0.40887(12) 0.0771(16) Uani 1 1 d . . . O2 O 0.4161(7) 0.4532(7) 0.30939(12) 0.0812(17) Uani 1 1 d . . . O3 O 0.2028(7) 0.2658(6) 0.28125(12) 0.0897(19) Uani 1 1 d . . . O4 O -0.2809(8) 0.1248(8) 0.26625(17) 0.113(2) Uani 1 1 d . . . O5 O 0.1190(9) 0.0975(7) 0.20081(14) 0.107(2) Uani 1 1 d . . . C1 C 0.3944(9) 0.5762(9) 0.3520(2) 0.069(2) Uani 1 1 d . . . H1 H 0.3439 0.502 0.3609 0.083 Uiso 1 1 calc R . . C2 C 0.4398(10) 0.5639(11) 0.3258(2) 0.076(3) Uani 1 1 d . . . C3 C 0.5207(10) 0.6780(11) 0.31244(19) 0.079(3) Uani 1 1 d . . . H3 H 0.5532 0.6697 0.2944 0.095 Uiso 1 1 calc R . . C4 C 0.5498(10) 0.7949(11) 0.3254(2) 0.080(3) Uani 1 1 d . . . H4 H 0.603 0.8664 0.3161 0.096 Uiso 1 1 calc R . . C5 C 0.5322(9) 0.9371(10) 0.3669(2) 0.070(2) Uani 1 1 d . . . H5 H 0.5879 1.0098 0.3584 0.085 Uiso 1 1 calc R . . C6 C 0.4798(10) 0.9511(9) 0.3930(2) 0.068(2) Uani 1 1 d . . . C7 C 0.3948(10) 0.8430(11) 0.40610(19) 0.078(2) Uani 1 1 d . . . H7 H 0.355 0.8553 0.4236 0.094 Uiso 1 1 calc R . . C8 C 0.3705(10) 0.7223(10) 0.3935(2) 0.077(3) Uani 1 1 d . . . H8 H 0.3184 0.6498 0.4027 0.093 Uiso 1 1 calc R . . C9 C 0.4236(9) 0.7039(10) 0.3663(2) 0.071(2) Uani 1 1 d . . . C10 C 0.5038(9) 0.8163(10) 0.3527(2) 0.068(2) Uani 1 1 d . . . C11 C 0.5766(10) 1.1882(9) 0.3972(2) 0.085(3) Uani 1 1 d . . . H11A H 0.5143 1.2238 0.3814 0.102 Uiso 1 1 calc R . . H11B H 0.6902 1.1617 0.3917 0.102 Uiso 1 1 calc R . . C12 C 0.5804(12) 1.2964(9) 0.4179(2) 0.089(3) Uani 1 1 d . . . H12A H 0.4658 1.3175 0.4237 0.107 Uiso 1 1 calc R . . H12B H 0.6219 1.3814 0.4096 0.107 Uiso 1 1 calc R . . C13 C 0.6868(11) 1.2599(9) 0.4430(2) 0.089(3) Uani 1 1 d . . . H13A H 0.6483 1.1728 0.4509 0.107 Uiso 1 1 calc R . . H13B H 0.8022 1.2427 0.4372 0.107 Uiso 1 1 calc R . . C14 C 0.6856(12) 1.3647(10) 0.4640(2) 0.106(3) Uani 1 1 d . . . H14A H 0.5695 1.3875 0.4687 0.127 Uiso 1 1 calc R . . H14B H 0.7325 1.4495 0.4565 0.127 Uiso 1 1 calc R . . C15 C 0.7815(15) 1.3232(12) 0.4900(3) 0.146(5) Uani 1 1 d . . . H15A H 0.752 1.2282 0.4949 0.175 Uiso 1 1 calc R . . H15B H 0.9005 1.3194 0.4856 0.175 Uiso 1 1 calc R . . C16 C 0.7604(18) 1.4081(14) 0.5141(3) 0.174(6) Uani 1 1 d . . . H16A H 0.8328 1.3704 0.5283 0.26 Uiso 1 1 calc R . . H16B H 0.6454 1.4068 0.5199 0.26 Uiso 1 1 calc R . . H16C H 0.7889 1.5031 0.5099 0.26 Uiso 1 1 calc R . . C17 C 0.3433(11) 0.3362(11) 0.32104(19) 0.089(3) Uani 1 1 d . . . H17A H 0.2319 0.3627 0.3276 0.107 Uiso 1 1 calc R . . H17B H 0.4109 0.3019 0.3364 0.107 Uiso 1 1 calc R . . C18 C 0.3307(10) 0.2228(9) 0.30096(18) 0.082(3) Uani 1 1 d . . . H18A H 0.438 0.2069 0.292 0.099 Uiso 1 1 calc R . . H18B H 0.3009 0.136 0.31 0.099 Uiso 1 1 calc R . . C19 C 0.1457(10) 0.1557(9) 0.26659(18) 0.084(3) Uani 1 1 d . . . H19A H 0.0997 0.0852 0.2786 0.101 Uiso 1 1 calc R . . H19B H 0.2369 0.1121 0.2564 0.101 Uiso 1 1 calc R . . C20 C 0.0120(11) 0.2164(9) 0.24781(18) 0.086(3) Uani 1 1 d . . . H20A H -0.0671 0.2734 0.2582 0.103 Uiso 1 1 calc R . . H20B H 0.0639 0.278 0.2347 0.103 Uiso 1 1 calc R . . C21 C -0.3315(11) -0.0281(9) 0.2298(2) 0.071(2) Uani 1 1 d . . . C22 C -0.4813(13) -0.0708(10) 0.2415(2) 0.093(3) Uani 1 1 d . . . H22 H -0.5148 -0.0412 0.2586 0.111 Uiso 1 1 calc R . . C23 C -0.5777(13) -0.1595(11) 0.2264(3) 0.108(3) Uani 1 1 d . . . H23 H -0.6802 -0.186 0.2335 0.13 Uiso 1 1 calc R . . C24 C -0.5309(12) -0.2094(10) 0.2021(3) 0.090(3) Uani 1 1 d . . . H24 H -0.601 -0.2689 0.193 0.108 Uiso 1 1 calc R . . C25 C -0.3138(13) -0.2216(8) 0.1651(2) 0.078(3) Uani 1 1 d . . . C26 C -0.1592(12) -0.1872(10) 0.15618(19) 0.082(3) Uani 1 1 d . . . H26 H -0.1181 -0.2236 0.14 0.098 Uiso 1 1 calc R . . C27 C -0.0598(12) -0.0963(10) 0.1713(3) 0.097(3) Uani 1 1 d . . . H27 H 0.0467 -0.0746 0.1652 0.116 Uiso 1 1 calc R . . C28 C -0.1205(12) -0.0397(9) 0.1951(2) 0.073(3) Uani 1 1 d . . . C29 C -0.2777(10) -0.0777(8) 0.2050(2) 0.062(2) Uani 1 1 d . . . C30 C -0.3790(11) -0.1733(9) 0.1903(2) 0.072(2) Uani 1 1 d . . . C31 C -0.0147(13) 0.0609(9) 0.2093(2) 0.079(3) Uani 1 1 d . . . C32 C -0.2361(13) 0.0736(10) 0.2450(2) 0.080(3) Uani 1 1 d . . . C33 C -0.4173(13) -0.3086(11) 0.1459(2) 0.089(3) Uani 1 1 d DU . . C34 C -0.5386(12) -0.2210(11) 0.1275(2) 0.093(3) Uani 1 1 d DU . . C35 C -0.6530(14) -0.2911(15) 0.1086(2) 0.134(4) Uani 1 1 d DU . . C36 C -0.7465(19) -0.2146(18) 0.0861(3) 0.218(9) Uani 1 1 d DU . . C37 C -0.892(2) -0.285(2) 0.0726(4) 0.330(13) Uani 1 1 d DU . . C38 C -0.935(2) -0.2401(19) 0.0444(4) 0.392(16) Uani 1 1 d DU . . F1 F -0.5112(7) -0.4030(5) 0.15983(12) 0.1135(19) Uani 1 1 d U . . F2 F -0.3139(7) -0.3856(6) 0.13056(13) 0.117(2) Uani 1 1 d U . . F3 F -0.6273(9) -0.1299(8) 0.14146(15) 0.162(3) Uani 1 1 d DU . . F4 F -0.4419(8) -0.1430(7) 0.11153(16) 0.155(3) Uani 1 1 d DU . . F5 F -0.5862(16) -0.4037(12) 0.0999(3) 0.302(9) Uani 1 1 d DU . . F6 F -0.7760(16) -0.3385(14) 0.1257(2) 0.275(7) Uani 1 1 d DU . . F7 F -0.7846(16) -0.0921(13) 0.0927(3) 0.269(6) Uani 1 1 d DU . . F8 F -0.636(2) -0.206(2) 0.0650(4) 0.408(13) Uani 1 1 d DU . . F9 F -0.857(2) -0.4256(19) 0.0706(4) 0.393(11) Uani 1 1 d DU . . F10 F -1.029(4) -0.251(3) 0.0881(7) 0.61(2) Uani 1 1 d DU . . F11 F -0.973(2) -0.1029(18) 0.0469(4) 0.361(9) Uiso 1 1 d D . . F12 F -1.076(3) -0.3123(18) 0.0422(5) 0.398(10) Uiso 1 1 d D . . F13 F -0.831(4) -0.265(3) 0.0235(9) 0.79(3) Uiso 1 1 d D . . C39 C 0.0402(9) 1.1129(9) 0.36059(19) 0.073(2) Uani 1 1 d . . . H39 H 0.1111 1.0407 0.3675 0.087 Uiso 1 1 calc R . . C40 C -0.0496(10) 1.0938(10) 0.33729(19) 0.074(2) Uani 1 1 d . . . C41 C -0.1541(10) 1.2047(11) 0.32691(18) 0.077(2) Uani 1 1 d . . . H41 H -0.2161 1.1917 0.3112 0.093 Uiso 1 1 calc R . . C42 C -0.1666(10) 1.3290(10) 0.33917(19) 0.078(3) Uani 1 1 d . . . H42 H -0.2331 1.4016 0.3313 0.094 Uiso 1 1 calc R . . C43 C -0.0950(9) 1.4794(9) 0.37781(19) 0.072(2) Uani 1 1 d . . . H43 H -0.1626 1.5531 0.3706 0.086 Uiso 1 1 calc R . . C44 C -0.0114(10) 1.4964(10) 0.4018(2) 0.077(2) Uani 1 1 d . . . C45 C 0.0948(10) 1.3874(10) 0.41226(19) 0.077(2) Uani 1 1 d . . . H45 H 0.1541 1.3992 0.4283 0.093 Uiso 1 1 calc R . . C46 C 0.1112(10) 1.2645(11) 0.39896(19) 0.080(3) Uani 1 1 d . . . H46 H 0.1807 1.1925 0.4063 0.095 Uiso 1 1 calc R . . C47 C 0.0255(9) 1.2417(9) 0.37409(17) 0.065(2) Uani 1 1 d . . . C48 C -0.0802(10) 1.3523(10) 0.36395(17) 0.066(2) Uani 1 1 d . . . C49 C -0.1291(12) 1.7297(10) 0.4092(2) 0.091(3) Uani 1 1 d . . . H49A H -0.2423 1.6991 0.4061 0.11 Uiso 1 1 calc R . . H49B H -0.0882 1.7704 0.3924 0.11 Uiso 1 1 calc R . . C50 C -0.1301(12) 1.8347(9) 0.4306(2) 0.088(3) Uani 1 1 d . . . H50A H -0.1905 1.9192 0.424 0.106 Uiso 1 1 calc R . . H50B H -0.0151 1.8588 0.4344 0.106 Uiso 1 1 calc R . . C51 C -0.2100(12) 1.7862(10) 0.4569(2) 0.094(3) Uani 1 1 d . . . H51A H -0.3285 1.7728 0.4534 0.113 Uiso 1 1 calc R . . H51B H -0.1589 1.6955 0.4621 0.113 Uiso 1 1 calc R . . C52 C -0.1959(13) 1.8819(10) 0.4800(2) 0.100(3) Uani 1 1 d . . . H52A H -0.2389 1.9744 0.4742 0.12 Uiso 1 1 calc R . . H52B H -0.0773 1.8896 0.4842 0.12 Uiso 1 1 calc R . . C53 C -0.2839(13) 1.8422(11) 0.5056(2) 0.112(3) Uani 1 1 d . . . H53A H -0.4034 1.8419 0.5015 0.134 Uiso 1 1 calc R . . H53B H -0.248 1.7462 0.5103 0.134 Uiso 1 1 calc R . . C54 C -0.2636(15) 1.9264(12) 0.5299(2) 0.127(4) Uani 1 1 d . . . H54A H -0.3257 1.8864 0.5446 0.191 Uiso 1 1 calc R . . H54B H -0.3052 2.0209 0.5262 0.191 Uiso 1 1 calc R . . H54C H -0.1465 1.9269 0.5347 0.191 Uiso 1 1 calc R . . C55 C 0.0541(11) 0.8582(9) 0.33179(17) 0.077(2) Uani 1 1 d . . . H55A H 0.0313 0.837 0.3507 0.093 Uiso 1 1 calc R . . H55B H 0.1713 0.8816 0.3303 0.093 Uiso 1 1 calc R . . C56 C 0.0226(11) 0.7322(10) 0.3152(2) 0.088(3) Uani 1 1 d . . . H56A H 0.0704 0.6485 0.3243 0.105 Uiso 1 1 calc R . . H56B H -0.0977 0.7215 0.3133 0.105 Uiso 1 1 calc R . . C57 C 0.0608(17) 0.6305(12) 0.2715(3) 0.142(4) Uani 1 1 d . . . H57A H 0.1645 0.5929 0.2637 0.17 Uiso 1 1 calc R . . H57B H 0.007 0.5556 0.2814 0.17 Uiso 1 1 calc R . . C58 C -0.0511(13) 0.6907(10) 0.2504(2) 0.105(3) Uani 1 1 d . . . H58A H 0.0037 0.7675 0.2413 0.126 Uiso 1 1 calc R . . H58B H -0.1528 0.7289 0.2587 0.126 Uiso 1 1 calc R . . C59 C -0.3062(12) 0.4301(10) 0.2127(2) 0.082(3) Uani 1 1 d . . . C60 C -0.4588(14) 0.3641(14) 0.2138(3) 0.117(4) Uani 1 1 d . . . H60 H -0.5301 0.3824 0.2283 0.141 Uiso 1 1 calc R . . C61 C -0.5095(17) 0.2719(15) 0.1942(4) 0.127(5) Uani 1 1 d . . . H61 H -0.6092 0.2252 0.1963 0.153 Uiso 1 1 calc R . . C62 C -0.416(2) 0.2509(12) 0.1725(3) 0.133(5) Uani 1 1 d . . . H62 H -0.4556 0.1944 0.159 0.159 Uiso 1 1 calc R . . C63 C -0.145(2) 0.2888(11) 0.1465(3) 0.106(4) Uani 1 1 d . . . C64 C 0.0089(18) 0.3528(12) 0.1455(2) 0.112(3) Uani 1 1 d . . . H64 H 0.0819 0.3366 0.1311 0.134 Uiso 1 1 calc R . . C65 C 0.0525(13) 0.4412(11) 0.1661(3) 0.095(3) Uani 1 1 d . . . H65 H 0.1542 0.4858 0.1649 0.114 Uiso 1 1 calc R . . C66 C -0.0466(12) 0.4656(9) 0.1881(2) 0.075(2) Uani 1 1 d . . . C67 C -0.2044(13) 0.4031(9) 0.1898(2) 0.076(3) Uani 1 1 d . . . C68 C -0.2512(15) 0.3131(11) 0.1690(3) 0.096(3) Uani 1 1 d . . . C69 C 0.0096(14) 0.5587(10) 0.2081(2) 0.080(3) Uani 1 1 d . . . C70 C -0.2537(15) 0.5221(11) 0.2340(3) 0.097(3) Uani 1 1 d . . . C71 C -0.186(2) 0.2047(13) 0.1226(3) 0.148(5) Uani 1 1 d DU . . C72 C -0.290(2) 0.2884(14) 0.1002(3) 0.156(6) Uani 1 1 d DU . . C73 C -0.324(3) 0.2137(16) 0.0730(4) 0.229(9) Uani 1 1 d DU . . C74 C -0.452(3) 0.2682(17) 0.0537(3) 0.236(10) Uani 1 1 d DU . . C75 C -0.462(4) 0.231(2) 0.0248(4) 0.268(11) Uani 1 1 d DU . . C76 C -0.622(3) 0.249(3) 0.0117(4) 0.279(14) Uani 1 1 d DU . . N2 N -0.0978(11) 0.5851(7) 0.22979(18) 0.087(2) Uani 1 1 d . . . O6 O -0.0231(7) 1.6141(7) 0.41747(12) 0.0843(17) Uani 1 1 d . . . O7 O -0.0491(6) 0.9732(6) 0.32290(12) 0.0801(17) Uani 1 1 d . . . O8 O 0.0947(9) 0.7470(7) 0.28957(16) 0.111(2) Uani 1 1 d . . . O9 O -0.3384(10) 0.5475(9) 0.25368(19) 0.138(3) Uani 1 1 d . . . O10 O 0.1427(10) 0.6179(7) 0.20760(14) 0.118(2) Uani 1 1 d . . . F14 F -0.2726(13) 0.0888(7) 0.12959(15) 0.188(4) Uani 1 1 d DU . . F15 F -0.0412(16) 0.1575(8) 0.10992(19) 0.199(4) Uani 1 1 d DU . . F16 F -0.2140(11) 0.4015(8) 0.09370(15) 0.167(3) Uani 1 1 d DU . . F17 F -0.4366(12) 0.3255(9) 0.11145(18) 0.164(3) Uani 1 1 d DU . . F18 F -0.175(3) 0.1928(19) 0.0597(3) 0.350(11) Uani 1 1 d DU . . F19 F -0.358(2) 0.0825(10) 0.0787(2) 0.302(9) Uani 1 1 d DU . . F20 F -0.606(3) 0.243(3) 0.0653(4) 0.412(14) Uani 1 1 d DU . . F21 F -0.455(2) 0.4039(12) 0.0547(2) 0.274(7) Uani 1 1 d DU . . F22 F -0.344(3) 0.305(3) 0.0116(5) 0.423(14) Uani 1 1 d DU . . F23 F -0.448(3) 0.0921(19) 0.0265(3) 0.463(16) Uani 1 1 d DU . . F24 F -0.583(3) 0.2183(18) -0.0134(4) 0.368(10) Uani 1 1 d DU . . F25 F -0.668(3) 0.382(2) 0.0115(3) 0.364(11) Uani 1 1 d DU . . F26 F -0.754(3) 0.178(3) 0.0198(7) 0.53(2) Uani 1 1 d DU . . 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 0.074(5) 0.077(5) 0.083(7) -0.015(5) -0.022(5) -0.013(4) O1 0.072(3) 0.089(4) 0.071(4) -0.003(4) 0.017(3) -0.014(3) O2 0.082(4) 0.093(4) 0.071(5) -0.009(4) 0.004(3) -0.024(3) O3 0.089(4) 0.080(4) 0.101(5) -0.018(4) -0.035(4) -0.008(3) O4 0.102(5) 0.153(6) 0.085(6) -0.042(5) -0.003(4) 0.009(4) O5 0.078(4) 0.136(6) 0.109(6) -0.007(4) -0.008(4) -0.034(4) C1 0.060(5) 0.096(7) 0.053(7) -0.011(6) 0.002(5) -0.012(4) C2 0.054(5) 0.101(8) 0.073(8) -0.010(7) -0.011(5) 0.000(5) C3 0.074(6) 0.099(7) 0.066(7) -0.008(7) 0.008(5) -0.024(5) C4 0.072(5) 0.101(8) 0.068(8) 0.006(6) 0.003(5) -0.019(5) C5 0.052(5) 0.083(7) 0.077(8) -0.002(6) 0.001(5) -0.012(5) C6 0.064(5) 0.074(6) 0.068(8) -0.018(6) 0.014(5) -0.006(5) C7 0.081(6) 0.091(7) 0.064(7) -0.014(6) 0.013(5) -0.012(5) C8 0.081(6) 0.093(7) 0.059(7) 0.001(6) 0.004(5) -0.026(5) C9 0.055(5) 0.090(7) 0.067(8) -0.009(6) 0.003(5) 0.006(5) C10 0.053(5) 0.085(7) 0.065(8) 0.013(6) -0.002(5) -0.021(5) C11 0.072(5) 0.087(6) 0.096(8) 0.015(6) 0.005(5) -0.011(5) C12 0.099(7) 0.073(6) 0.096(8) -0.008(6) 0.002(6) -0.013(5) C13 0.085(6) 0.079(6) 0.105(8) -0.031(6) 0.007(6) -0.013(5) C14 0.093(7) 0.095(7) 0.131(10) -0.013(7) 0.003(7) -0.015(5) C15 0.144(9) 0.134(9) 0.159(12) -0.051(9) -0.086(10) 0.023(8) C16 0.208(14) 0.159(11) 0.151(13) -0.048(10) -0.068(11) 0.049(10) C17 0.082(6) 0.112(8) 0.073(7) -0.010(7) -0.009(5) 0.003(6) C18 0.075(5) 0.103(7) 0.069(6) -0.016(6) -0.017(5) 0.001(5) C19 0.085(6) 0.079(6) 0.087(7) 0.003(6) -0.018(5) -0.015(5) C20 0.093(6) 0.080(6) 0.086(7) -0.010(5) -0.033(6) -0.007(5) C21 0.065(6) 0.075(6) 0.072(8) -0.007(6) -0.013(6) 0.003(5) C22 0.080(6) 0.125(8) 0.076(7) -0.018(6) -0.013(6) -0.023(6) C23 0.088(7) 0.139(9) 0.101(10) -0.018(8) 0.008(8) -0.025(7) C24 0.084(7) 0.092(7) 0.097(9) -0.006(7) 0.002(6) -0.022(5) C25 0.082(7) 0.065(6) 0.087(8) -0.006(6) -0.016(6) 0.006(5) C26 0.072(6) 0.097(7) 0.079(7) -0.025(5) 0.004(6) -0.010(5) C27 0.079(6) 0.093(7) 0.120(10) 0.003(7) 0.003(7) -0.017(6) C28 0.077(7) 0.068(6) 0.072(7) -0.005(5) -0.015(6) 0.004(5) C29 0.055(5) 0.064(5) 0.068(7) -0.007(5) -0.003(5) -0.003(5) C30 0.069(6) 0.070(6) 0.078(8) -0.001(6) 0.000(6) -0.004(5) C31 0.070(6) 0.082(6) 0.086(9) -0.008(6) -0.014(6) -0.013(6) C32 0.078(7) 0.087(7) 0.074(8) -0.009(6) -0.018(7) 0.009(6) C33 0.100(7) 0.085(7) 0.085(8) -0.016(6) 0.001(7) -0.022(6) C34 0.092(7) 0.108(8) 0.079(8) -0.011(7) -0.005(7) -0.011(7) C35 0.104(8) 0.188(12) 0.112(11) -0.025(10) 0.006(8) -0.041(9) C36 0.212(14) 0.233(16) 0.202(16) -0.095(13) -0.175(14) 0.110(13) C37 0.33(2) 0.37(3) 0.29(2) -0.04(2) -0.276(19) 0.02(2) C38 0.35(3) 0.43(3) 0.41(3) 0.02(3) -0.25(3) -0.16(3) F1 0.139(4) 0.089(4) 0.115(5) -0.006(3) -0.032(4) -0.033(3) F2 0.119(4) 0.113(4) 0.121(5) -0.053(4) -0.017(4) 0.013(3) F3 0.173(6) 0.191(7) 0.118(6) -0.053(5) -0.047(5) 0.078(5) F4 0.139(5) 0.161(6) 0.166(7) 0.056(5) -0.037(5) -0.055(5) F5 0.318(14) 0.250(10) 0.331(16) -0.202(11) -0.242(13) 0.155(10) F6 0.272(11) 0.351(15) 0.211(11) 0.081(10) -0.101(10) -0.190(12) F7 0.303(13) 0.233(10) 0.262(12) -0.028(9) -0.167(10) 0.105(10) F8 0.37(2) 0.52(3) 0.34(2) 0.019(19) 0.226(19) -0.039(18) F9 0.371(18) 0.361(18) 0.45(2) -0.177(17) -0.306(17) 0.048(15) F10 0.49(3) 0.74(5) 0.62(4) -0.19(4) 0.38(3) -0.15(3) C39 0.060(5) 0.085(6) 0.073(7) -0.011(6) 0.003(5) -0.001(4) C40 0.075(6) 0.086(7) 0.062(7) -0.028(6) -0.001(5) -0.009(5) C41 0.072(5) 0.090(7) 0.068(7) 0.003(6) -0.009(5) 0.009(5) C42 0.071(5) 0.091(7) 0.071(7) 0.002(6) -0.003(5) 0.013(5) C43 0.057(5) 0.083(7) 0.075(7) -0.001(6) -0.003(5) -0.002(4) C44 0.057(5) 0.094(7) 0.079(8) -0.007(6) 0.014(5) -0.012(5) C45 0.063(5) 0.092(7) 0.077(7) -0.013(6) -0.011(5) 0.003(5) C46 0.065(5) 0.103(7) 0.070(7) -0.003(6) -0.010(5) 0.004(5) C47 0.051(5) 0.086(6) 0.057(6) -0.013(5) 0.012(5) -0.007(5) C48 0.061(5) 0.084(6) 0.055(6) -0.002(5) -0.002(5) -0.008(5) C49 0.107(7) 0.081(6) 0.086(8) -0.002(6) 0.001(6) 0.010(6) C50 0.109(7) 0.081(6) 0.075(8) -0.018(6) 0.000(6) -0.007(5) C51 0.097(6) 0.106(7) 0.080(8) -0.029(7) 0.005(6) 0.000(6) C52 0.114(7) 0.093(7) 0.093(9) 0.008(7) -0.003(7) -0.009(6) C53 0.127(8) 0.119(8) 0.091(9) -0.020(7) 0.030(7) -0.029(7) C54 0.153(10) 0.150(9) 0.080(9) -0.024(8) 0.033(7) -0.021(8) C55 0.087(6) 0.089(6) 0.057(6) -0.018(5) -0.006(5) -0.004(6) C56 0.079(6) 0.100(7) 0.084(8) -0.010(7) 0.014(6) 0.012(5) C57 0.190(12) 0.102(8) 0.130(11) 0.001(8) -0.031(10) 0.036(8) C58 0.114(7) 0.085(7) 0.116(9) 0.008(7) -0.011(7) 0.005(6) C59 0.065(6) 0.095(7) 0.086(9) 0.007(6) 0.000(6) -0.019(6) C60 0.089(8) 0.152(10) 0.110(10) 0.049(9) -0.010(7) -0.023(8) C61 0.103(9) 0.134(11) 0.146(14) 0.044(11) -0.041(10) -0.059(8) C62 0.163(13) 0.084(8) 0.151(14) 0.044(10) -0.080(10) -0.036(9) C63 0.165(12) 0.069(7) 0.084(10) -0.010(7) -0.033(9) 0.002(8) C64 0.158(11) 0.090(7) 0.088(9) -0.014(7) -0.002(8) -0.015(8) C65 0.093(7) 0.109(8) 0.083(9) -0.001(7) 0.008(7) -0.021(6) C66 0.079(6) 0.078(6) 0.068(8) -0.009(6) -0.012(6) -0.017(5) C67 0.087(7) 0.066(6) 0.078(8) 0.002(6) -0.025(7) -0.020(5) C68 0.101(8) 0.066(6) 0.120(11) 0.021(7) -0.028(8) -0.023(6) C69 0.089(7) 0.096(7) 0.056(8) -0.009(6) 0.010(7) -0.014(6) C70 0.102(9) 0.108(8) 0.081(10) -0.003(8) -0.007(8) -0.005(7) C71 0.235(15) 0.080(9) 0.129(14) -0.030(9) -0.058(12) -0.001(10) C72 0.263(17) 0.091(9) 0.114(12) -0.014(9) -0.078(13) -0.011(12) C73 0.39(2) 0.121(12) 0.175(18) -0.086(12) -0.102(18) 0.052(15) C74 0.44(3) 0.119(11) 0.145(14) -0.049(10) -0.187(17) 0.056(14) C75 0.46(3) 0.206(18) 0.136(16) -0.063(15) -0.12(2) 0.01(2) C76 0.46(4) 0.27(2) 0.097(14) -0.011(17) -0.15(2) 0.02(3) N2 0.098(6) 0.080(5) 0.083(7) -0.017(5) -0.017(6) -0.022(5) O6 0.079(4) 0.090(4) 0.084(5) -0.024(4) 0.006(3) -0.003(3) O7 0.072(3) 0.084(4) 0.083(5) -0.015(4) -0.005(3) 0.006(3) O8 0.147(6) 0.099(5) 0.089(6) -0.035(4) -0.001(5) -0.026(4) O9 0.129(6) 0.189(8) 0.100(7) -0.031(6) 0.039(5) -0.014(5) O10 0.112(5) 0.143(6) 0.105(6) -0.027(5) 0.002(4) -0.061(5) F14 0.340(11) 0.080(4) 0.144(6) -0.005(4) -0.117(7) -0.030(5) F15 0.325(12) 0.140(6) 0.130(8) -0.071(5) -0.048(8) 0.064(7) F16 0.260(9) 0.109(5) 0.133(6) 0.006(4) -0.023(6) -0.015(5) F17 0.197(7) 0.163(7) 0.131(7) 0.015(5) -0.048(6) -0.013(6) F18 0.46(2) 0.38(2) 0.196(15) -0.144(13) -0.132(15) 0.166(19) F19 0.62(2) 0.125(6) 0.171(9) 0.016(6) -0.214(13) -0.110(10) F20 0.321(19) 0.63(4) 0.29(2) 0.04(2) -0.035(16) -0.03(2) F21 0.49(2) 0.158(8) 0.169(9) -0.006(7) -0.153(12) -0.010(10) F22 0.41(3) 0.53(3) 0.34(3) -0.02(2) 0.07(2) -0.07(2) F23 0.82(4) 0.246(14) 0.315(18) -0.156(13) -0.37(2) 0.136(19) F24 0.50(3) 0.342(19) 0.255(17) -0.027(15) -0.127(19) 0.012(18) F25 0.56(3) 0.291(15) 0.228(14) -0.012(13) -0.213(16) 0.071(18) F26 0.45(3) 0.55(4) 0.58(5) 0.09(3) -0.06(3) -0.22(3) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C31 1.391(11) . ? N1 C32 1.424(11) . ? N1 C20 1.455(10) . ? O1 C6 1.388(9) . ? O1 C11 1.442(9) . ? O2 C2 1.361(10) . ? O2 C17 1.390(10) . ? O3 C19 1.378(9) . ? O3 C18 1.444(9) . ? O4 C32 1.214(10) . ? O5 C31 1.204(10) . ? C1 C2 1.350(11) . ? C1 C9 1.446(11) . ? C1 H1 0.93 . ? C2 C3 1.434(12) . ? C3 C4 1.323(11) . ? C3 H3 0.93 . ? C4 C10 1.416(12) . ? C4 H4 0.93 . ? C5 C6 1.360(11) . ? C5 C10 1.385(11) . ? C5 H5 0.93 . ? C6 C7 1.403(11) . ? C7 C8 1.339(11) . ? C7 H7 0.93 . ? C8 C9 1.418(11) . ? C8 H8 0.93 . ? C9 C10 1.425(11) . ? C11 C12 1.467(11) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 C13 1.520(12) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 C14 1.456(12) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 C15 1.523(14) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C15 C16 1.458(15) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 H16A 0.96 . ? C16 H16B 0.96 . ? C16 H16C 0.96 . ? C17 C18 1.487(11) . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? C18 H18A 0.97 . ? C18 H18B 0.97 . ? C19 C20 1.497(10) . ? C19 H19A 0.97 . ? C19 H19B 0.97 . ? C20 H20A 0.97 . ? C20 H20B 0.97 . ? C21 C29 1.383(11) . ? C21 C22 1.398(12) . ? C21 C32 1.472(12) . ? C22 C23 1.389(13) . ? C22 H22 0.93 . ? C23 C24 1.348(12) . ? C23 H23 0.93 . ? C24 C30 1.396(12) . ? C24 H24 0.93 . ? C25 C26 1.357(12) . ? C25 C30 1.425(12) . ? C25 C33 1.530(12) . ? C26 C27 1.418(13) . ? C26 H26 0.93 . ? C27 C28 1.381(12) . ? C27 H27 0.93 . ? C28 C29 1.402(12) . ? C28 C31 1.484(12) . ? C29 C30 1.444(12) . ? C33 F2 1.328(10) . ? C33 F1 1.369(10) . ? C33 C34 1.530(10) . ? C34 F3 1.306(10) . ? C34 F4 1.337(10) . ? C34 C35 1.487(10) . ? C35 F5 1.261(12) . ? C35 F6 1.379(12) . ? C35 C36 1.493(13) . ? C36 F7 1.245(13) . ? C36 F8 1.367(16) . ? C36 C37 1.516(15) . ? C37 F9 1.363(17) . ? C37 F10 1.365(19) . ? C37 C38 1.485(15) . ? C38 F11 1.338(5) . ? C38 F13 1.341(6) . ? C38 F12 1.342(5) . ? C39 C40 1.369(11) . ? C39 C47 1.410(11) . ? C39 H39 0.93 . ? C40 O7 1.363(9) . ? C40 C41 1.403(11) . ? C41 C42 1.341(11) . ? C41 H41 0.93 . ? C42 C48 1.425(11) . ? C42 H42 0.93 . ? C43 C44 1.371(12) . ? C43 C48 1.404(11) . ? C43 H43 0.93 . ? C44 O6 1.375(10) . ? C44 C45 1.400(11) . ? C45 C46 1.356(11) . ? C45 H45 0.93 . ? C46 C47 1.425(11) . ? C46 H46 0.93 . ? C47 C48 1.403(11) . ? C49 O6 1.411(9) . ? C49 C50 1.471(11) . ? C49 H49A 0.97 . ? C49 H49B 0.97 . ? C50 C51 1.514(12) . ? C50 H50A 0.97 . ? C50 H50B 0.97 . ? C51 C52 1.482(12) . ? C51 H51A 0.97 . ? C51 H51B 0.97 . ? C52 C53 1.493(13) . ? C52 H52A 0.97 . ? C52 H52B 0.97 . ? C53 C54 1.467(13) . ? C53 H53A 0.97 . ? C53 H53B 0.97 . ? C54 H54A 0.96 . ? C54 H54B 0.96 . ? C54 H54C 0.96 . ? C55 O7 1.403(9) . ? C55 C56 1.496(11) . ? C55 H55A 0.97 . ? C55 H55B 0.97 . ? C56 O8 1.395(10) . ? C56 H56A 0.97 . ? C56 H56B 0.97 . ? C57 C58 1.461(13) . ? C57 O8 1.469(12) . ? C57 H57A 0.97 . ? C57 H57B 0.97 . ? C58 N2 1.501(11) . ? C58 H58A 0.97 . ? C58 H58B 0.97 . ? C59 C60 1.389(13) . ? C59 C67 1.413(12) . ? C59 C70 1.454(14) . ? C60 C61 1.390(16) . ? C60 H60 0.93 . ? C61 C62 1.318(17) . ? C61 H61 0.93 . ? C62 C68 1.468(17) . ? C62 H62 0.93 . ? C63 C64 1.387(15) . ? C63 C68 1.417(15) . ? C63 C71 1.483(16) . ? C64 C65 1.387(14) . ? C64 H64 0.93 . ? C65 C66 1.359(12) . ? C65 H65 0.93 . ? C66 C67 1.413(12) . ? C66 C69 1.424(12) . ? C67 C68 1.408(14) . ? C69 O10 1.219(10) . ? C69 N2 1.391(11) . ? C70 O9 1.207(11) . ? C70 N2 1.413(13) . ? C71 F14 1.362(12) . ? C71 F15 1.377(13) . ? C71 C72 1.561(19) . ? C72 F16 1.292(13) . ? C72 F17 1.329(14) . ? C72 C73 1.56(2) . ? C73 F19 1.314(15) . ? C73 F18 1.369(17) . ? C73 C74 1.46(2) . ? C74 F21 1.294(13) . ? C74 F20 1.380(18) . ? C74 C75 1.48(3) . ? C75 F23 1.321(16) . ? C75 F22 1.359(18) . ? C75 C76 1.43(3) . ? C76 F25 1.300(17) . ? C76 F24 1.313(16) . ? C76 F26 1.327(19) . ? 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 C31 N1 C32 125.0(8) . . ? C31 N1 C20 118.7(8) . . ? C32 N1 C20 116.3(9) . . ? C6 O1 C11 118.2(7) . . ? C2 O2 C17 117.0(8) . . ? C19 O3 C18 113.1(6) . . ? C2 C1 C9 120.5(9) . . ? C2 C1 H1 119.8 . . ? C9 C1 H1 119.8 . . ? C1 C2 O2 127.5(9) . . ? C1 C2 C3 119.2(9) . . ? O2 C2 C3 113.4(10) . . ? C4 C3 C2 121.0(10) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C10 123.1(9) . . ? C3 C4 H4 118.5 . . ? C10 C4 H4 118.5 . . ? C6 C5 C10 121.1(9) . . ? C6 C5 H5 119.4 . . ? C10 C5 H5 119.4 . . ? C5 C6 O1 126.4(9) . . ? C5 C6 C7 120.4(8) . . ? O1 C6 C7 113.1(9) . . ? C8 C7 C6 120.3(9) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 120.7(9) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C10 118.6(9) . . ? C8 C9 C1 121.8(9) . . ? C10 C9 C1 119.5(10) . . ? C5 C10 C4 124.6(9) . . ? C5 C10 C9 118.7(10) . . ? C4 C10 C9 116.7(9) . . ? O1 C11 C12 107.8(7) . . ? O1 C11 H11A 110.1 . . ? C12 C11 H11A 110.1 . . ? O1 C11 H11B 110.1 . . ? C12 C11 H11B 110.1 . . ? H11A C11 H11B 108.5 . . ? C11 C12 C13 116.0(7) . . ? C11 C12 H12A 108.3 . . ? C13 C12 H12A 108.3 . . ? C11 C12 H12B 108.3 . . ? C13 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? C14 C13 C12 116.2(8) . . ? C14 C13 H13A 108.2 . . ? C12 C13 H13A 108.2 . . ? C14 C13 H13B 108.2 . . ? C12 C13 H13B 108.2 . . ? H13A C13 H13B 107.4 . . ? C13 C14 C15 116.0(9) . . ? C13 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? C13 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C16 C15 C14 119.9(10) . . ? C16 C15 H15A 107.3 . . ? C14 C15 H15A 107.3 . . ? C16 C15 H15B 107.3 . . ? C14 C15 H15B 107.3 . . ? H15A C15 H15B 106.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O2 C17 C18 110.7(8) . . ? O2 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? O2 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? O3 C18 C17 108.3(7) . . ? O3 C18 H18A 110 . . ? C17 C18 H18A 110 . . ? O3 C18 H18B 110 . . ? C17 C18 H18B 110 . . ? H18A C18 H18B 108.4 . . ? O3 C19 C20 106.5(7) . . ? O3 C19 H19A 110.4 . . ? C20 C19 H19A 110.4 . . ? O3 C19 H19B 110.4 . . ? C20 C19 H19B 110.4 . . ? H19A C19 H19B 108.6 . . ? N1 C20 C19 114.6(7) . . ? N1 C20 H20A 108.6 . . ? C19 C20 H20A 108.6 . . ? N1 C20 H20B 108.6 . . ? C19 C20 H20B 108.6 . . ? H20A C20 H20B 107.6 . . ? C29 C21 C22 121.5(9) . . ? C29 C21 C32 122.1(9) . . ? C22 C21 C32 116.4(11) . . ? C23 C22 C21 116.7(10) . . ? C23 C22 H22 121.6 . . ? C21 C22 H22 121.6 . . ? C24 C23 C22 123.6(10) . . ? C24 C23 H23 118.2 . . ? C22 C23 H23 118.2 . . ? C23 C24 C30 121.1(10) . . ? C23 C24 H24 119.5 . . ? C30 C24 H24 119.5 . . ? C26 C25 C30 121.7(8) . . ? C26 C25 C33 116.2(10) . . ? C30 C25 C33 122.1(9) . . ? C25 C26 C27 120.5(10) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C28 C27 C26 120.4(9) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C27 C28 C29 119.8(9) . . ? C27 C28 C31 117.9(10) . . ? C29 C28 C31 122.4(11) . . ? C21 C29 C28 119.1(9) . . ? C21 C29 C30 120.1(8) . . ? C28 C29 C30 120.8(10) . . ? C24 C30 C25 126.4(10) . . ? C24 C30 C29 116.8(10) . . ? C25 C30 C29 116.8(8) . . ? O5 C31 N1 121.2(9) . . ? O5 C31 C28 123.5(12) . . ? N1 C31 C28 115.3(10) . . ? O4 C32 N1 119.3(9) . . ? O4 C32 C21 124.7(10) . . ? N1 C32 C21 115.9(10) . . ? F2 C33 F1 105.3(8) . . ? F2 C33 C34 109.1(8) . . ? F1 C33 C34 107.0(8) . . ? F2 C33 C25 109.3(8) . . ? F1 C33 C25 111.5(8) . . ? C34 C33 C25 114.1(8) . . ? F3 C34 F4 104.6(9) . . ? F3 C34 C35 108.6(9) . . ? F4 C34 C35 105.0(9) . . ? F3 C34 C33 111.1(8) . . ? F4 C34 C33 105.9(8) . . ? C35 C34 C33 120.3(9) . . ? F5 C35 F6 102.7(13) . . ? F5 C35 C34 111.4(9) . . ? F6 C35 C34 102.5(9) . . ? F5 C35 C36 109.7(11) . . ? F6 C35 C36 105.0(11) . . ? C34 C35 C36 123.1(12) . . ? F7 C36 F8 107.1(18) . . ? F7 C36 C35 110.3(11) . . ? F8 C36 C35 105.9(14) . . ? F7 C36 C37 112.4(14) . . ? F8 C36 C37 101.1(14) . . ? C35 C36 C37 118.8(14) . . ? F9 C37 F10 114(2) . . ? F9 C37 C38 103.2(17) . . ? F10 C37 C38 106(2) . . ? F9 C37 C36 110.6(14) . . ? F10 C37 C36 105(2) . . ? C38 C37 C36 117.4(16) . . ? F11 C38 F13 111.7(9) . . ? F11 C38 F12 110.8(9) . . ? F13 C38 F12 111.4(9) . . ? F11 C38 C37 102.3(17) . . ? F13 C38 C37 122(3) . . ? F12 C38 C37 97.2(17) . . ? C40 C39 C47 120.2(8) . . ? C40 C39 H39 119.9 . . ? C47 C39 H39 119.9 . . ? O7 C40 C39 125.5(9) . . ? O7 C40 C41 115.4(8) . . ? C39 C40 C41 119.1(8) . . ? C42 C41 C40 121.5(8) . . ? C42 C41 H41 119.3 . . ? C40 C41 H41 119.3 . . ? C41 C42 C48 121.5(8) . . ? C41 C42 H42 119.2 . . ? C48 C42 H42 119.2 . . ? C44 C43 C48 121.0(8) . . ? C44 C43 H43 119.5 . . ? C48 C43 H43 119.5 . . ? C43 C44 O6 125.4(9) . . ? C43 C44 C45 119.6(9) . . ? O6 C44 C45 114.9(9) . . ? C46 C45 C44 119.9(9) . . ? C46 C45 H45 120.1 . . ? C44 C45 H45 120.1 . . ? C45 C46 C47 122.4(8) . . ? C45 C46 H46 118.8 . . ? C47 C46 H46 118.8 . . ? C48 C47 C39 120.9(8) . . ? C48 C47 C46 116.8(8) . . ? C39 C47 C46 122.2(9) . . ? C47 C48 C43 120.2(8) . . ? C47 C48 C42 116.8(8) . . ? C43 C48 C42 123.0(9) . . ? O6 C49 C50 108.6(8) . . ? O6 C49 H49A 110 . . ? C50 C49 H49A 110 . . ? O6 C49 H49B 110 . . ? C50 C49 H49B 110 . . ? H49A C49 H49B 108.4 . . ? C49 C50 C51 114.0(8) . . ? C49 C50 H50A 108.8 . . ? C51 C50 H50A 108.8 . . ? C49 C50 H50B 108.8 . . ? C51 C50 H50B 108.8 . . ? H50A C50 H50B 107.7 . . ? C52 C51 C50 115.7(8) . . ? C52 C51 H51A 108.4 . . ? C50 C51 H51A 108.4 . . ? C52 C51 H51B 108.4 . . ? C50 C51 H51B 108.4 . . ? H51A C51 H51B 107.4 . . ? C51 C52 C53 117.0(9) . . ? C51 C52 H52A 108 . . ? C53 C52 H52A 108 . . ? C51 C52 H52B 108 . . ? C53 C52 H52B 108 . . ? H52A C52 H52B 107.3 . . ? C54 C53 C52 119.6(9) . . ? C54 C53 H53A 107.4 . . ? C52 C53 H53A 107.4 . . ? C54 C53 H53B 107.4 . . ? C52 C53 H53B 107.4 . . ? H53A C53 H53B 107 . . ? C53 C54 H54A 109.5 . . ? C53 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? C53 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? O7 C55 C56 110.4(7) . . ? O7 C55 H55A 109.6 . . ? C56 C55 H55A 109.6 . . ? O7 C55 H55B 109.6 . . ? C56 C55 H55B 109.6 . . ? H55A C55 H55B 108.1 . . ? O8 C56 C55 110.3(8) . . ? O8 C56 H56A 109.6 . . ? C55 C56 H56A 109.6 . . ? O8 C56 H56B 109.6 . . ? C55 C56 H56B 109.6 . . ? H56A C56 H56B 108.1 . . ? C58 C57 O8 105.5(8) . . ? C58 C57 H57A 110.6 . . ? O8 C57 H57A 110.6 . . ? C58 C57 H57B 110.6 . . ? O8 C57 H57B 110.6 . . ? H57A C57 H57B 108.8 . . ? C57 C58 N2 112.7(8) . . ? C57 C58 H58A 109.1 . . ? N2 C58 H58A 109.1 . . ? C57 C58 H58B 109.1 . . ? N2 C58 H58B 109.1 . . ? H58A C58 H58B 107.8 . . ? C60 C59 C67 116.7(11) . . ? C60 C59 C70 121.7(12) . . ? C67 C59 C70 121.6(9) . . ? C59 C60 C61 122.9(12) . . ? C59 C60 H60 118.6 . . ? C61 C60 H60 118.6 . . ? C62 C61 C60 119.8(13) . . ? C62 C61 H61 120.1 . . ? C60 C61 H61 120.1 . . ? C61 C62 C68 122.6(14) . . ? C61 C62 H62 118.7 . . ? C68 C62 H62 118.7 . . ? C64 C63 C68 118.9(10) . . ? C64 C63 C71 115.6(15) . . ? C68 C63 C71 125.4(15) . . ? C65 C64 C63 119.4(11) . . ? C65 C64 H64 120.3 . . ? C63 C64 H64 120.3 . . ? C66 C65 C64 123.0(10) . . ? C66 C65 H65 118.5 . . ? C64 C65 H65 118.5 . . ? C65 C66 C67 119.3(9) . . ? C65 C66 C69 118.6(10) . . ? C67 C66 C69 122.0(11) . . ? C68 C67 C66 118.5(11) . . ? C68 C67 C59 122.8(10) . . ? C66 C67 C59 118.6(10) . . ? C67 C68 C63 120.8(10) . . ? C67 C68 C62 115.1(13) . . ? C63 C68 C62 124.1(14) . . ? O10 C69 N2 117.8(9) . . ? O10 C69 C66 125.3(10) . . ? N2 C69 C66 117.0(10) . . ? O9 C70 N2 121.4(11) . . ? O9 C70 C59 123.0(12) . . ? N2 C70 C59 115.5(11) . . ? F14 C71 F15 106.8(11) . . ? F14 C71 C63 112.2(13) . . ? F15 C71 C63 110.4(13) . . ? F14 C71 C72 107.7(11) . . ? F15 C71 C72 105.3(14) . . ? C63 C71 C72 114.0(10) . . ? F16 C72 F17 108.2(12) . . ? F16 C72 C73 105.9(14) . . ? F17 C72 C73 109.0(15) . . ? F16 C72 C71 109.3(12) . . ? F17 C72 C71 106.3(14) . . ? C73 C72 C71 117.9(12) . . ? F19 C73 F18 99.7(16) . . ? F19 C73 C74 107.1(17) . . ? F18 C73 C74 109(2) . . ? F19 C73 C72 108.2(16) . . ? F18 C73 C72 108.9(19) . . ? C74 C73 C72 121.7(14) . . ? F21 C74 F20 99.9(19) . . ? F21 C74 C73 107.5(14) . . ? F20 C74 C73 106(2) . . ? F21 C74 C75 107.5(17) . . ? F20 C74 C75 108(2) . . ? C73 C74 C75 125(2) . . ? F23 C75 F22 121(3) . . ? F23 C75 C76 100(2) . . ? F22 C75 C76 111(2) . . ? F23 C75 C74 101.6(17) . . ? F22 C75 C74 107(2) . . ? C76 C75 C74 117(2) . . ? F25 C76 F24 106.8(18) . . ? F25 C76 F26 108(2) . . ? F24 C76 F26 110(2) . . ? F25 C76 C75 109(2) . . ? F24 C76 C75 101(2) . . ? F26 C76 C75 121(2) . . ? C69 N2 C70 125.1(9) . . ? C69 N2 C58 119.3(8) . . ? C70 N2 C58 115.6(10) . . ? C44 O6 C49 119.8(7) . . ? C40 O7 C55 118.8(7) . . ? C56 O8 C57 113.3(8) . . ? # Attachment 'Molecule4.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-10-14 at 12:07:37 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : struct orig dreduc data_struct_615875 _database_code_depnum_ccdc_archive 'CCDC 615875' _audit_creation_date 2006-10-14T12:07:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C30 H17 N1 O2' _chemical_formula_weight 423.45 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a b' _symmetry_space_group_name_Hall '-P 2bc 2ac' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z+1/2' 'x+1/2, -y, -z+1/2' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, y-1/2, -z-1/2' '-x-1/2, y, z-1/2' 'x-1/2, -y-1/2, z' _cell_length_a 9.329(5) _cell_length_b 17.981(5) _cell_length_c 25.306(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4245(3) _cell_formula_units_Z 8 _cell_measurement_temperature 293 _cell_measurement_reflns_used 18082 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1760 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.443805E-1 _diffrn_orient_matrix_ub_12 -0.317643E-1 _diffrn_orient_matrix_ub_13 -0.280091E-1 _diffrn_orient_matrix_ub_21 -0.248116E-1 _diffrn_orient_matrix_ub_22 -0.382102E-1 _diffrn_orient_matrix_ub_23 0.272177E-1 _diffrn_orient_matrix_ub_31 -0.943716E-1 _diffrn_orient_matrix_ub_32 0.249839E-1 _diffrn_orient_matrix_ub_33 0.6016E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_unetI/netI 0.0602 _diffrn_reflns_number 9140 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 4850 _reflns_number_gt 2475 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; 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^)+(0.0791P)^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 noref _refine_ls_extinction_method none _refine_ls_number_reflns 4850 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.131 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1236 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.135 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_number_in_cell C 240 H 136 N 8 O 16 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 C1 C 1.03923(18) 0.16253(9) 0.32486(7) 0.0466(5) Uani 1 1 d . . . C2 C 1.0090(2) 0.17910(10) 0.27316(8) 0.0576(5) Uani 1 1 d . . . H2 H 0.9146 0.1873 0.2629 0.069 Uiso 1 1 calc R . . C3 C 1.1186(2) 0.18376(12) 0.23578(9) 0.0682(6) Uani 1 1 d . . . H3 H 1.0972 0.195 0.2008 0.082 Uiso 1 1 calc R . . C4 C 1.2575(2) 0.17175(11) 0.25073(9) 0.0678(6) Uani 1 1 d . . . H4 H 1.3297 0.1753 0.2255 0.081 Uiso 1 1 calc R . . C5 C 1.4362(2) 0.14223(11) 0.32020(11) 0.0684(6) Uani 1 1 d . . . H5 H 1.5109 0.1448 0.2959 0.082 Uiso 1 1 calc R . . C6 C 1.4657(2) 0.12693(11) 0.37165(11) 0.0700(7) Uani 1 1 d . . . H6 H 1.5602 0.1199 0.3823 0.084 Uiso 1 1 calc R . . C7 C 1.35468(19) 0.12169(10) 0.40882(9) 0.0598(6) Uani 1 1 d . . . H7 H 1.3759 0.111 0.4439 0.072 Uiso 1 1 calc R . . C8 C 1.21490(17) 0.13230(9) 0.39366(8) 0.0473(5) Uani 1 1 d . . . C9 C 1.18207(18) 0.14969(9) 0.34080(8) 0.0468(5) Uani 1 1 d . . . C10 C 1.2944(2) 0.15420(10) 0.30307(9) 0.0548(5) Uani 1 1 d . . . C11 C 1.10031(18) 0.12807(10) 0.43336(9) 0.0494(5) Uani 1 1 d . . . C12 C 0.92160(19) 0.15786(10) 0.36348(8) 0.0490(5) Uani 1 1 d . . . C13 C 0.84413(18) 0.13377(10) 0.45385(7) 0.0468(5) Uani 1 1 d . . . C14 C 0.8103(2) 0.06486(10) 0.47473(8) 0.0578(5) Uani 1 1 d . . . H14 H 0.8639 0.0231 0.4657 0.069 Uiso 1 1 calc R . . C15 C 0.6963(2) 0.05879(11) 0.50906(8) 0.0629(6) Uani 1 1 d . . . H15 H 0.6739 0.0126 0.5234 0.076 Uiso 1 1 calc R . . C16 C 0.6143(2) 0.12022(11) 0.52264(8) 0.0557(5) Uani 1 1 d . . . C17 C 0.6507(2) 0.18877(11) 0.50189(8) 0.0594(5) Uani 1 1 d . . . H17 H 0.5971 0.2306 0.5107 0.071 Uiso 1 1 calc R . . C18 C 0.76628(19) 0.19541(10) 0.46823(8) 0.0565(5) Uani 1 1 d . . . H18 H 0.7917 0.2419 0.4552 0.068 Uiso 1 1 calc R . . C19 C 0.4918(2) 0.11202(12) 0.55650(8) 0.0640(6) Uani 1 1 d . . . C20 C 0.3872(2) 0.10418(12) 0.58328(9) 0.0665(6) Uani 1 1 d . . . C21 C 0.2587(2) 0.09132(11) 0.61338(8) 0.0592(5) Uani 1 1 d . . . C22 C 0.2533(2) 0.03193(11) 0.65024(9) 0.0689(6) Uani 1 1 d . . . H22 H 0.3344 0.0031 0.6562 0.083 Uiso 1 1 calc R . . C23 C 0.1297(2) 0.01710(11) 0.67681(9) 0.0725(6) Uani 1 1 d . . . H23 H 0.1281 -0.0217 0.7011 0.087 Uiso 1 1 calc R . . C24 C -0.1268(3) 0.04286(15) 0.69427(10) 0.0898(8) Uani 1 1 d . . . H24 H -0.1319 0.0036 0.7181 0.108 Uiso 1 1 calc R . . C25 C -0.2457(3) 0.0848(2) 0.68428(13) 0.1061(10) Uani 1 1 d . . . H25 H -0.332 0.0729 0.7006 0.127 Uiso 1 1 calc R . . C26 C -0.2390(3) 0.1452(2) 0.64981(13) 0.1079(10) Uani 1 1 d . . . H26 H -0.3201 0.1743 0.6443 0.129 Uiso 1 1 calc R . . C27 C -0.1157(2) 0.16222(16) 0.62427(10) 0.0897(8) Uani 1 1 d . . . H27 H -0.1132 0.2024 0.6011 0.108 Uiso 1 1 calc R . . C28 C 0.1388(2) 0.13382(12) 0.60564(8) 0.0645(6) Uani 1 1 d . . . H28 H 0.1427 0.1734 0.582 0.077 Uiso 1 1 calc R . . C29 C 0.0093(2) 0.11927(13) 0.63251(8) 0.0639(6) Uani 1 1 d . . . C30 C 0.0046(2) 0.05889(12) 0.66848(9) 0.0670(6) Uani 1 1 d . . . N1 N 0.95946(14) 0.14064(7) 0.41583(6) 0.0473(4) Uani 1 1 d . . . O1 O 0.79690(13) 0.16798(8) 0.35163(6) 0.0655(4) Uani 1 1 d . . . O2 O 1.12235(14) 0.11514(8) 0.47988(6) 0.0702(4) Uani 1 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 C1 0.0447(11) 0.0468(10) 0.0482(12) -0.0003(8) 0.0036(9) -0.0021(8) C2 0.0591(12) 0.0609(12) 0.0528(13) 0.0007(10) 0.0016(11) 0.0008(9) C3 0.0807(16) 0.0737(14) 0.0502(13) 0.0008(11) 0.0126(12) 0.0000(12) C4 0.0716(15) 0.0671(13) 0.0649(16) -0.0068(11) 0.0268(13) -0.0070(11) C5 0.0487(13) 0.0646(13) 0.092(2) -0.0081(12) 0.0207(12) -0.0013(10) C6 0.0379(11) 0.0663(14) 0.106(2) -0.0069(13) 0.0041(13) 0.0015(10) C7 0.0457(12) 0.0558(11) 0.0778(16) -0.0015(10) -0.0047(11) 0.0023(9) C8 0.0364(10) 0.0463(10) 0.0593(13) -0.0036(9) 0.0001(9) -0.0013(8) C9 0.0428(10) 0.0423(9) 0.0552(13) -0.0058(9) 0.0076(9) -0.0027(8) C10 0.0482(12) 0.0504(10) 0.0658(15) -0.0072(9) 0.0131(10) -0.0024(9) C11 0.0426(11) 0.0510(10) 0.0545(13) 0.0010(9) -0.0032(10) -0.0001(8) C12 0.0398(11) 0.0530(11) 0.0542(13) 0.0033(9) 0.0005(9) -0.0006(8) C13 0.0384(10) 0.0551(11) 0.0469(11) 0.0007(9) 0.0025(9) -0.0017(8) C14 0.0580(12) 0.0510(11) 0.0646(14) 0.0021(10) 0.0088(11) 0.0003(9) C15 0.0633(13) 0.0604(12) 0.0651(14) 0.0082(10) 0.0158(11) -0.0092(10) C16 0.0463(11) 0.0702(13) 0.0505(12) -0.0015(10) 0.0051(10) -0.0063(10) C17 0.0529(12) 0.0612(12) 0.0643(14) -0.0050(10) 0.0102(11) 0.0051(9) C18 0.0534(12) 0.0518(11) 0.0642(14) 0.0059(10) 0.0092(10) 0.0003(9) C19 0.0580(13) 0.0804(14) 0.0537(13) -0.0050(11) 0.0076(12) -0.0088(11) C20 0.0603(13) 0.0841(15) 0.0551(13) -0.0074(11) 0.0085(12) -0.0120(11) C21 0.0578(12) 0.0730(13) 0.0468(12) -0.0099(11) 0.0118(10) -0.0115(11) C22 0.0699(13) 0.0650(12) 0.0717(16) -0.0061(12) 0.0135(12) -0.0011(11) C23 0.0878(15) 0.0577(12) 0.0719(16) -0.0036(10) 0.0247(13) -0.0102(12) C24 0.0873(18) 0.0911(17) 0.0910(19) -0.0279(15) 0.0374(16) -0.0280(15) C25 0.0690(18) 0.145(3) 0.104(3) -0.045(2) 0.0328(17) -0.0302(19) C26 0.0615(17) 0.174(3) 0.088(2) -0.033(2) 0.0038(15) 0.0037(18) C27 0.0644(15) 0.137(2) 0.0673(17) -0.0053(15) -0.0012(13) 0.0079(16) C28 0.0650(14) 0.0843(15) 0.0442(12) 0.0010(11) 0.0054(11) -0.0083(12) C29 0.0543(13) 0.0934(16) 0.0440(12) -0.0133(11) 0.0017(10) -0.0096(11) C30 0.0662(14) 0.0758(14) 0.0589(14) -0.0208(12) 0.0196(11) -0.0211(12) N1 0.0380(9) 0.0558(9) 0.0479(10) 0.0042(7) 0.0028(7) -0.0005(7) O1 0.0404(8) 0.0919(10) 0.0642(10) 0.0123(7) -0.0018(7) 0.0046(7) O2 0.0579(9) 0.0987(11) 0.0542(10) 0.0090(8) -0.0075(7) 0.0005(7) #----------------------------------------------------------------------------# # 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 C1 C2 1.371(3) . ? C1 C9 1.411(3) . ? C1 C12 1.472(3) . ? C2 C3 1.395(3) . ? C2 H2 0.93 . ? C3 C4 1.367(3) . ? C3 H3 0.93 . ? C4 C10 1.404(3) . ? C4 H4 0.93 . ? C5 C6 1.359(3) . ? C5 C10 1.409(3) . ? C5 H5 0.93 . ? C6 C7 1.402(3) . ? C6 H6 0.93 . ? C7 C8 1.373(3) . ? C7 H7 0.93 . ? C8 C9 1.407(3) . ? C8 C11 1.469(3) . ? C9 C10 1.420(3) . ? C11 O2 1.217(2) . ? C11 N1 1.405(2) . ? C12 O1 1.215(2) . ? C12 N1 1.405(2) . ? C13 C18 1.374(2) . ? C13 C14 1.383(2) . ? C13 N1 1.449(2) . ? C14 C15 1.378(3) . ? C14 H14 0.93 . ? C15 C16 1.387(3) . ? C15 H15 0.93 . ? C16 C17 1.382(3) . ? C16 C19 1.436(3) . ? C17 C18 1.379(3) . ? C17 H17 0.93 . ? C18 H18 0.93 . ? C19 C20 1.196(3) . ? C20 C21 1.439(3) . ? C21 C28 1.369(3) . ? C21 C22 1.419(3) . ? C22 C23 1.361(3) . ? C22 H22 0.93 . ? C23 C30 1.405(3) . ? C23 H23 0.93 . ? C24 C25 1.364(4) . ? C24 C30 1.418(3) . ? C24 H24 0.93 . ? C25 C26 1.396(4) . ? C25 H25 0.93 . ? C26 C27 1.354(3) . ? C26 H26 0.93 . ? C27 C29 1.414(3) . ? C27 H27 0.93 . ? C28 C29 1.410(3) . ? C28 H28 0.93 . ? C29 C30 1.418(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9 120.14(17) . . ? C2 C1 C12 119.53(17) . . ? C9 C1 C12 120.33(17) . . ? C1 C2 C3 120.63(19) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C10 121.91(19) . . ? C3 C4 H4 119 . . ? C10 C4 H4 119 . . ? C6 C5 C10 121.1(2) . . ? C6 C5 H5 119.5 . . ? C10 C5 H5 119.5 . . ? C5 C6 C7 120.5(2) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 120.3(2) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 120.23(18) . . ? C7 C8 C11 119.53(19) . . ? C9 C8 C11 120.21(16) . . ? C8 C9 C1 120.89(16) . . ? C8 C9 C10 119.41(18) . . ? C1 C9 C10 119.70(19) . . ? C4 C10 C5 123.68(19) . . ? C4 C10 C9 117.79(18) . . ? C5 C10 C9 118.5(2) . . ? O2 C11 N1 119.60(17) . . ? O2 C11 C8 123.25(17) . . ? N1 C11 C8 117.14(18) . . ? O1 C12 N1 120.42(16) . . ? O1 C12 C1 122.77(18) . . ? N1 C12 C1 116.81(15) . . ? C18 C13 C14 120.05(17) . . ? C18 C13 N1 119.97(15) . . ? C14 C13 N1 119.96(15) . . ? C15 C14 C13 119.20(17) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 121.26(18) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C17 C16 C15 118.70(18) . . ? C17 C16 C19 120.95(18) . . ? C15 C16 C19 120.33(18) . . ? C18 C17 C16 120.28(18) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C13 C18 C17 120.45(17) . . ? C13 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C20 C19 C16 177.8(2) . . ? C19 C20 C21 176.6(2) . . ? C28 C21 C22 119.02(18) . . ? C28 C21 C20 121.0(2) . . ? C22 C21 C20 119.90(19) . . ? C23 C22 C21 120.2(2) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C30 121.7(2) . . ? C22 C23 H23 119.2 . . ? C30 C23 H23 119.2 . . ? C25 C24 C30 120.3(3) . . ? C25 C24 H24 119.8 . . ? C30 C24 H24 119.8 . . ? C24 C25 C26 120.6(2) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C27 C26 C25 120.8(3) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C26 C27 C29 120.5(3) . . ? C26 C27 H27 119.8 . . ? C29 C27 H27 119.8 . . ? C21 C28 C29 121.8(2) . . ? C21 C28 H28 119.1 . . ? C29 C28 H28 119.1 . . ? C28 C29 C27 122.3(2) . . ? C28 C29 C30 118.6(2) . . ? C27 C29 C30 119.1(2) . . ? C23 C30 C29 118.68(19) . . ? C23 C30 C24 122.7(2) . . ? C29 C30 C24 118.6(2) . . ? C11 N1 C12 124.62(15) . . ? C11 N1 C13 118.10(16) . . ? C12 N1 C13 117.27(14) . . ? _chemical_name_common ps04.178 # Attachment 'Molecule5.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-10-16 at 08:09:21 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\wingx\files\archive.dat # CIF files read : struct import dreduc data_struct_615876 _database_code_depnum_ccdc_archive 'CCDC 615876' _audit_creation_date 2006-10-16T08:09:21-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C26 H21 N1 O4' _chemical_formula_weight 411.44 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.140(5) _cell_length_b 5.718(5) _cell_length_c 29.183(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 96.673(5) _cell_angle_gamma 90.000(5) _cell_volume 2012(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 3593 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.56212E-1 _diffrn_orient_matrix_ub_12 0.653863E-1 _diffrn_orient_matrix_ub_13 -0.189762E-1 _diffrn_orient_matrix_ub_21 0.609435E-1 _diffrn_orient_matrix_ub_22 -0.650786E-1 _diffrn_orient_matrix_ub_23 0.223758E-1 _diffrn_orient_matrix_ub_31 -0.19561E-2 _diffrn_orient_matrix_ub_32 -0.148568 _diffrn_orient_matrix_ub_33 -0.181531E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_unetI/netI 0.031 _diffrn_reflns_number 6298 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.988 _reflns_number_total 3513 _reflns_number_gt 2508 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; 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^)+(0.0641P)^2^+0.2006P] 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 noref _refine_ls_extinction_method none _refine_ls_number_reflns 3513 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.151 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.052 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_number_in_cell C 104 H 84 N 4 O 16 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 C1 C 0.17147(13) 0.1237(3) 0.29394(5) 0.0502(4) Uani 1 1 d . . . C2 C 0.08145(13) -0.0199(3) 0.29320(5) 0.0494(4) Uani 1 1 d . . . H2 H 0.0775 -0.1549 0.2753 0.059 Uiso 1 1 calc R . . C3 C -0.09915(13) -0.1102(3) 0.32083(6) 0.0583(4) Uani 1 1 d . . . H3 H -0.1044 -0.2474 0.3036 0.07 Uiso 1 1 calc R . . C4 C -0.18169(15) -0.0539(4) 0.34680(7) 0.0712(6) Uani 1 1 d . . . H4 H -0.2423 -0.1532 0.3472 0.085 Uiso 1 1 calc R . . C5 C -0.17610(16) 0.1508(4) 0.37278(7) 0.0729(6) Uani 1 1 d . . . H5 H -0.2327 0.1878 0.3904 0.087 Uiso 1 1 calc R . . C6 C -0.08785(16) 0.2966(3) 0.37229(6) 0.0648(5) Uani 1 1 d . . . H6 H -0.0848 0.4334 0.3896 0.078 Uiso 1 1 calc R . . C7 C 0.09334(15) 0.3890(3) 0.34504(6) 0.0613(5) Uani 1 1 d . . . H7 H 0.0981 0.5273 0.3619 0.074 Uiso 1 1 calc R . . C8 C 0.17670(14) 0.3305(3) 0.32014(6) 0.0598(5) Uani 1 1 d . . . H8 H 0.238 0.4282 0.3204 0.072 Uiso 1 1 calc R . . C9 C -0.00621(12) 0.0354(3) 0.31958(5) 0.0461(4) Uani 1 1 d . . . C10 C -0.00078(13) 0.2437(3) 0.34589(5) 0.0501(4) Uani 1 1 d . . . C11 C 0.26817(15) -0.1350(3) 0.24907(6) 0.0644(5) Uani 1 1 d . . . H11A H 0.2094 -0.1499 0.2237 0.077 Uiso 1 1 calc R . . H11B H 0.2591 -0.2583 0.2712 0.077 Uiso 1 1 calc R . . C12 C 0.37818(15) -0.1593(4) 0.23143(6) 0.0707(5) Uani 1 1 d . . . H12A H 0.4368 -0.1156 0.2554 0.085 Uiso 1 1 calc R . . H12B H 0.3897 -0.3208 0.223 0.085 Uiso 1 1 calc R . . C13 C 0.47407(13) -0.0562(4) 0.16862(6) 0.0636(5) Uani 1 1 d . . . H13A H 0.4792 -0.2209 0.1612 0.076 Uiso 1 1 calc R . . H13B H 0.5422 -0.009 0.187 0.076 Uiso 1 1 calc R . . C14 C 0.45469(13) 0.0878(3) 0.12540(6) 0.0606(5) Uani 1 1 d . . . H14A H 0.3867 0.0363 0.1075 0.073 Uiso 1 1 calc R . . H14B H 0.4451 0.2501 0.1337 0.073 Uiso 1 1 calc R . . C15 C 0.71868(12) 0.2282(3) 0.07380(5) 0.0485(4) Uani 1 1 d . . . C16 C 0.80392(14) 0.3870(3) 0.07955(6) 0.0619(5) Uani 1 1 d . . . H16 H 0.8053 0.5007 0.1024 0.074 Uiso 1 1 calc R . . C17 C 0.88913(15) 0.3778(4) 0.05088(7) 0.0720(6) Uani 1 1 d . . . H17 H 0.9472 0.4845 0.0551 0.086 Uiso 1 1 calc R . . C18 C 0.88734(15) 0.2147(4) 0.01719(7) 0.0699(5) Uani 1 1 d . . . H18 H 0.9438 0.2135 -0.0018 0.084 Uiso 1 1 calc R . . C19 C 0.79731(16) -0.1298(4) -0.02385(6) 0.0691(5) Uani 1 1 d . . . H19 H 0.8521 -0.1365 -0.0436 0.083 Uiso 1 1 calc R . . C20 C 0.71442(17) -0.2898(4) -0.02834(6) 0.0710(5) Uani 1 1 d . . . H20 H 0.7132 -0.4054 -0.0508 0.085 Uiso 1 1 calc R . . C21 C 0.63115(15) -0.2818(3) 0.00058(6) 0.0633(5) Uani 1 1 d . . . H21 H 0.5746 -0.3923 -0.0028 0.076 Uiso 1 1 calc R . . C22 C 0.63116(13) -0.1134(3) 0.03408(5) 0.0493(4) Uani 1 1 d . . . C23 C 0.71642(12) 0.0544(3) 0.03948(5) 0.0462(4) Uani 1 1 d . . . C24 C 0.80227(13) 0.0471(3) 0.01017(6) 0.0557(4) Uani 1 1 d . . . C25 C 0.54152(13) -0.1078(3) 0.06413(6) 0.0541(4) Uani 1 1 d . . . C26 C 0.63018(13) 0.2371(3) 0.10414(6) 0.0535(4) Uani 1 1 d . . . N1 N 0.54577(10) 0.0711(2) 0.09680(4) 0.0518(4) Uani 1 1 d . . . O1 O 0.26099(9) 0.0870(2) 0.27059(4) 0.0612(3) Uani 1 1 d . . . O2 O 0.38186(9) -0.0143(2) 0.19271(4) 0.0704(4) Uani 1 1 d . . . O3 O 0.46562(10) -0.2481(2) 0.06099(5) 0.0770(4) Uani 1 1 d . . . O4 O 0.62841(11) 0.3800(3) 0.13482(5) 0.0839(4) Uani 1 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 C1 0.0521(9) 0.0576(10) 0.0423(9) 0.0096(8) 0.0111(7) -0.0035(8) C2 0.0564(10) 0.0491(9) 0.0440(9) -0.0010(7) 0.0111(7) -0.0031(8) C3 0.0566(10) 0.0565(10) 0.0639(11) 0.0012(9) 0.0151(8) -0.0069(8) C4 0.0589(11) 0.0716(13) 0.0872(15) 0.0184(11) 0.0254(10) -0.0025(9) C5 0.0740(13) 0.0769(14) 0.0743(13) 0.0196(11) 0.0358(10) 0.0197(11) C6 0.0840(13) 0.0571(11) 0.0564(11) 0.0014(9) 0.0213(10) 0.0163(10) C7 0.0751(12) 0.0450(9) 0.0632(11) -0.0062(8) 0.0058(9) -0.0041(9) C8 0.0617(11) 0.0523(10) 0.0655(12) 0.0041(9) 0.0081(9) -0.0135(8) C9 0.0500(9) 0.0466(9) 0.0425(9) 0.0061(7) 0.0088(7) 0.0002(7) C10 0.0598(10) 0.0456(9) 0.0454(9) 0.0038(7) 0.0083(7) 0.0051(8) C11 0.0649(11) 0.0736(12) 0.0583(11) 0.0064(10) 0.0227(9) 0.0016(9) C12 0.0629(11) 0.0911(14) 0.0615(12) 0.0207(11) 0.0216(9) 0.0135(10) C13 0.0495(10) 0.0919(13) 0.0527(10) 0.0015(10) 0.0200(8) 0.0087(9) C14 0.0471(9) 0.0868(13) 0.0502(10) -0.0026(9) 0.0156(8) 0.0031(9) C15 0.0471(9) 0.0553(10) 0.0423(9) 0.0073(8) 0.0013(7) -0.0014(7) C16 0.0624(11) 0.0625(11) 0.0589(11) 0.0050(9) -0.0011(9) -0.0108(9) C17 0.0569(11) 0.0782(13) 0.0809(14) 0.0182(12) 0.0076(10) -0.0197(10) C18 0.0557(11) 0.0892(14) 0.0678(13) 0.0208(12) 0.0198(9) -0.0028(10) C19 0.0717(12) 0.0909(14) 0.0487(10) 0.0079(10) 0.0235(9) 0.0196(11) C20 0.0851(14) 0.0777(13) 0.0515(11) -0.0095(10) 0.0137(10) 0.0119(11) C21 0.0732(12) 0.0637(11) 0.0531(11) -0.0069(9) 0.0079(9) -0.0051(9) C22 0.0517(9) 0.0569(10) 0.0397(9) 0.0005(8) 0.0065(7) -0.0009(8) C23 0.0450(8) 0.0556(10) 0.0378(8) 0.0076(7) 0.0046(7) 0.0036(7) C24 0.0505(10) 0.0695(11) 0.0483(10) 0.0138(9) 0.0115(8) 0.0080(8) C25 0.0514(10) 0.0642(11) 0.0466(10) 0.0000(8) 0.0051(7) -0.0058(8) C26 0.0537(10) 0.0629(11) 0.0435(9) -0.0039(8) 0.0043(7) -0.0019(8) N1 0.0459(7) 0.0684(9) 0.0427(8) -0.0046(7) 0.0113(6) -0.0035(6) O1 0.0583(7) 0.0734(8) 0.0551(7) 0.0062(6) 0.0201(6) -0.0074(6) O2 0.0575(7) 0.0988(9) 0.0598(8) 0.0193(7) 0.0283(6) 0.0175(6) O3 0.0694(8) 0.0875(9) 0.0762(9) -0.0121(7) 0.0179(7) -0.0299(7) O4 0.0866(9) 0.0969(10) 0.0713(9) -0.0362(8) 0.0213(7) -0.0154(8) #----------------------------------------------------------------------------# # 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 C1 O1 1.3644(18) . ? C1 C2 1.365(2) . ? C1 C8 1.406(2) . ? C2 C9 1.420(2) . ? C2 H2 0.93 . ? C3 C4 1.363(2) . ? C3 C9 1.406(2) . ? C3 H3 0.93 . ? C4 C5 1.392(3) . ? C4 H4 0.93 . ? C5 C6 1.359(3) . ? C5 H5 0.93 . ? C6 C10 1.411(2) . ? C6 H6 0.93 . ? C7 C8 1.354(2) . ? C7 C10 1.415(2) . ? C7 H7 0.93 . ? C8 H8 0.93 . ? C9 C10 1.414(2) . ? C11 O1 1.424(2) . ? C11 C12 1.493(2) . ? C11 H11A 0.97 . ? C11 H11B 0.97 . ? C12 O2 1.406(2) . ? C12 H12A 0.97 . ? C12 H12B 0.97 . ? C13 O2 1.4099(18) . ? C13 C14 1.502(2) . ? C13 H13A 0.97 . ? C13 H13B 0.97 . ? C14 N1 1.4639(19) . ? C14 H14A 0.97 . ? C14 H14B 0.97 . ? C15 C16 1.373(2) . ? C15 C23 1.409(2) . ? C15 C26 1.470(2) . ? C16 C17 1.405(2) . ? C16 H16 0.93 . ? C17 C18 1.353(3) . ? C17 H17 0.93 . ? C18 C24 1.406(3) . ? C18 H18 0.93 . ? C19 C20 1.355(3) . ? C19 C24 1.414(3) . ? C19 H19 0.93 . ? C20 C21 1.391(2) . ? C20 H20 0.93 . ? C21 C22 1.372(2) . ? C21 H21 0.93 . ? C22 C23 1.407(2) . ? C22 C25 1.475(2) . ? C23 C24 1.424(2) . ? C25 O3 1.2172(19) . ? C25 N1 1.395(2) . ? C26 O4 1.2139(19) . ? C26 N1 1.395(2) . ? 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 C1 C2 125.60(15) . . ? O1 C1 C8 114.38(14) . . ? C2 C1 C8 120.02(15) . . ? C1 C2 C9 120.42(15) . . ? C1 C2 H2 119.8 . . ? C9 C2 H2 119.8 . . ? C4 C3 C9 121.22(17) . . ? C4 C3 H3 119.4 . . ? C9 C3 H3 119.4 . . ? C3 C4 C5 120.59(17) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 119.91(17) . . ? C6 C5 H5 120 . . ? C4 C5 H5 120 . . ? C5 C6 C10 121.06(17) . . ? C5 C6 H6 119.5 . . ? C10 C6 H6 119.5 . . ? C8 C7 C10 121.32(16) . . ? C8 C7 H7 119.3 . . ? C10 C7 H7 119.3 . . ? C7 C8 C1 120.67(15) . . ? C7 C8 H8 119.7 . . ? C1 C8 H8 119.7 . . ? C3 C9 C10 118.13(14) . . ? C3 C9 C2 122.43(15) . . ? C10 C9 C2 119.44(14) . . ? C6 C10 C9 119.08(15) . . ? C6 C10 C7 122.79(16) . . ? C9 C10 C7 118.12(15) . . ? O1 C11 C12 109.77(15) . . ? O1 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? O1 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? O2 C12 C11 109.61(14) . . ? O2 C12 H12A 109.7 . . ? C11 C12 H12A 109.7 . . ? O2 C12 H12B 109.7 . . ? C11 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? O2 C13 C14 105.64(13) . . ? O2 C13 H13A 110.6 . . ? C14 C13 H13A 110.6 . . ? O2 C13 H13B 110.6 . . ? C14 C13 H13B 110.6 . . ? H13A C13 H13B 108.7 . . ? N1 C14 C13 112.84(13) . . ? N1 C14 H14A 109 . . ? C13 C14 H14A 109 . . ? N1 C14 H14B 109 . . ? C13 C14 H14B 109 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C23 120.38(15) . . ? C16 C15 C26 119.77(16) . . ? C23 C15 C26 119.84(14) . . ? C15 C16 C17 119.94(18) . . ? C15 C16 H16 120 . . ? C17 C16 H16 120 . . ? C18 C17 C16 120.51(17) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C24 121.66(17) . . ? C17 C18 H18 119.2 . . ? C24 C18 H18 119.2 . . ? C20 C19 C24 121.45(16) . . ? C20 C19 H19 119.3 . . ? C24 C19 H19 119.3 . . ? C19 C20 C21 120.19(18) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 C20 121.04(17) . . ? C22 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C21 C22 C23 119.84(15) . . ? C21 C22 C25 120.00(15) . . ? C23 C22 C25 120.15(15) . . ? C22 C23 C15 120.93(14) . . ? C22 C23 C24 119.55(15) . . ? C15 C23 C24 119.51(15) . . ? C18 C24 C19 124.10(17) . . ? C18 C24 C23 117.97(17) . . ? C19 C24 C23 117.92(16) . . ? O3 C25 N1 120.16(15) . . ? O3 C25 C22 123.02(16) . . ? N1 C25 C22 116.82(14) . . ? O4 C26 N1 119.71(15) . . ? O4 C26 C15 122.99(15) . . ? N1 C26 C15 117.30(14) . . ? C25 N1 C26 124.90(13) . . ? C25 N1 C14 117.85(13) . . ? C26 N1 C14 117.25(14) . . ? C1 O1 C11 116.78(12) . . ? C12 O2 C13 113.69(13) . . ? # Attachment 'Molecule6.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-10-16 at 13:36:49 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\archive.dat # CIF files read : struct new dreduc data_struct_615877 _database_code_depnum_ccdc_archive 'CCDC 615877' _audit_creation_date 2006-10-16T13:36:49-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C36 H29 N1 O3' _chemical_formula_sum 'C36 H29 N1 O3' _chemical_formula_weight 523.6 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 24.8660(6) _cell_length_b 5.2750(2) _cell_length_c 21.6140(11) _cell_angle_alpha 90 _cell_angle_beta 101.0280(10) _cell_angle_gamma 90 _cell_volume 2782.72(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 5370 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 25.028 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.25 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9542 _exptl_absorpt_correction_T_max 0.9961 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.2278E-3 _diffrn_orient_matrix_ub_12 0.14008 _diffrn_orient_matrix_ub_13 -0.271332E-1 _diffrn_orient_matrix_ub_21 -0.471365E-1 _diffrn_orient_matrix_ub_22 0 _diffrn_orient_matrix_ub_23 -0.75492E-2 _diffrn_orient_matrix_ub_31 0.2498E-3 _diffrn_orient_matrix_ub_32 0.127722 _diffrn_orient_matrix_ub_33 0.297584E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_unetI/netI 0.0647 _diffrn_reflns_number 4894 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.05 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _reflns_number_total 4894 _reflns_number_gt 2316 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97 (Giacovazzo et al, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; 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^)+(0.0631P)^2^+0.5669P] 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 noref _refine_ls_extinction_method none _refine_ls_number_reflns 4894 _refine_ls_number_parameters 477 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1623 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1642 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.143 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.038 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_number_in_cell C 144 H 116 N 4 O 12 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 C1 C -0.04537(13) 0.2369(7) 0.34461(16) 0.0635(9) Uani 1 1 d . . . C2 C -0.09262(14) 0.2314(7) 0.36720(16) 0.0659(10) Uani 1 1 d . . . C3 C -0.10374(11) 0.4093(5) 0.41215(13) 0.0491(8) Uani 1 1 d . . . C4 C -0.15352(12) 0.4077(6) 0.43459(15) 0.0541(8) Uani 1 1 d . . . C5 C -0.16326(12) 0.5864(6) 0.47671(14) 0.0515(8) Uani 1 1 d . . . C6 C -0.12256(14) 0.7654(7) 0.49975(17) 0.0689(10) Uani 1 1 d . . . C7 C -0.07457(15) 0.7691(7) 0.47906(18) 0.0730(10) Uani 1 1 d . . . C8 C -0.06350(12) 0.5921(6) 0.43407(14) 0.0529(8) Uani 1 1 d . . . C9 C -0.01453(13) 0.5944(7) 0.41008(17) 0.0645(9) Uani 1 1 d . . . C10 C -0.00522(12) 0.4212(6) 0.36593(14) 0.0569(8) Uani 1 1 d . . . C11 C -0.25420(13) 0.4350(7) 0.47638(19) 0.0612(9) Uani 1 1 d . . . C12 C -0.30258(16) 0.5020(7) 0.5055(2) 0.0691(10) Uani 1 1 d . . . C13 C -0.3290(2) 0.7501(9) 0.4825(3) 0.0836(12) Uani 1 1 d . . . C14 C 0.04467(13) 0.4243(6) 0.34160(15) 0.0627(9) Uani 1 1 d . . . C15 C 0.08562(13) 0.4212(6) 0.32001(15) 0.0592(9) Uani 1 1 d . . . C16 C 0.22838(11) 0.4050(5) 0.23969(13) 0.0464(7) Uani 1 1 d . . . C17 C 0.18626(12) 0.2379(6) 0.22082(15) 0.0544(8) Uani 1 1 d . . . C18 C 0.13928(12) 0.2445(6) 0.24725(15) 0.0557(8) Uani 1 1 d . . . C19 C 0.13402(11) 0.4185(6) 0.29362(14) 0.0518(8) Uani 1 1 d . . . C20 C 0.17726(11) 0.5945(6) 0.31457(13) 0.0498(8) Uani 1 1 d . . . C21 C 0.17539(15) 0.7794(6) 0.36163(15) 0.0593(9) Uani 1 1 d . . . C22 C 0.21724(14) 0.9446(7) 0.38017(16) 0.0622(9) Uani 1 1 d . . . C23 C 0.26385(14) 0.9355(6) 0.35282(15) 0.0585(9) Uani 1 1 d . . . C24 C 0.26763(11) 0.7583(5) 0.30683(13) 0.0478(7) Uani 1 1 d . . . C25 C 0.22464(11) 0.5859(5) 0.28717(13) 0.0453(7) Uani 1 1 d . . . C26 C 0.31734(13) 0.7502(6) 0.27911(14) 0.0535(8) Uani 1 1 d . . . C27 C 0.27743(12) 0.3943(6) 0.21092(15) 0.0549(8) Uani 1 1 d . . . C28 C 0.36840(11) 0.5551(6) 0.20512(14) 0.0504(8) Uani 1 1 d . . . C29 C 0.40678(14) 0.3709(7) 0.22476(17) 0.0652(10) Uani 1 1 d . . . C30 C 0.45292(14) 0.3591(7) 0.19800(18) 0.0684(10) Uani 1 1 d . . . C31 C 0.46142(12) 0.5251(6) 0.15131(15) 0.0559(8) Uani 1 1 d . . . C32 C 0.42216(13) 0.7087(7) 0.13332(16) 0.0607(9) Uani 1 1 d . . . C33 C 0.37605(13) 0.7258(7) 0.15990(16) 0.0598(9) Uani 1 1 d . . . C34 C 0.51186(16) 0.5048(8) 0.1218(3) 0.0757(12) Uani 1 1 d . . . C35 C 0.5151(2) 0.2630(9) 0.0868(3) 0.0912(14) Uani 1 1 d . . . C36 C 0.5657(2) 0.2397(14) 0.0570(3) 0.1009(16) Uani 1 1 d . . . N1 N 0.31950(9) 0.5668(5) 0.23266(11) 0.0510(6) Uani 1 1 d . . . O1 O -0.21021(8) 0.6081(4) 0.50018(9) 0.0629(6) Uani 1 1 d . . . O2 O 0.35585(9) 0.8942(5) 0.29526(11) 0.0760(7) Uani 1 1 d . . . O3 O 0.28229(8) 0.2406(5) 0.17016(11) 0.0784(7) Uani 1 1 d . . . H1 H -0.0393(13) 0.112(6) 0.3140(16) 0.088(11) Uiso 1 1 d . . . H2 H -0.1200(12) 0.108(6) 0.3545(14) 0.075(11) Uiso 1 1 d . . . H4 H -0.1802(11) 0.288(5) 0.4172(12) 0.051(8) Uiso 1 1 d . . . H6 H -0.1313(12) 0.890(6) 0.5266(15) 0.074(10) Uiso 1 1 d . . . H7 H -0.0453(13) 0.893(6) 0.4975(15) 0.095(12) Uiso 1 1 d . . . H9 H 0.0108(13) 0.728(6) 0.4250(15) 0.084(11) Uiso 1 1 d . . . H11A H -0.2400(12) 0.244(7) 0.4897(15) 0.092(11) Uiso 1 1 d . . . H11B H -0.2620(11) 0.452(5) 0.4303(15) 0.068(10) Uiso 1 1 d . . . H12A H -0.2898(14) 0.504(7) 0.5529(18) 0.100(14) Uiso 1 1 d . . . H12B H -0.3305(12) 0.364(6) 0.4947(14) 0.074(10) Uiso 1 1 d . . . H13A H -0.3603(18) 0.784(8) 0.5040(19) 0.127(16) Uiso 1 1 d . . . H13B H -0.3462(18) 0.759(9) 0.440(2) 0.14(2) Uiso 1 1 d . . . H13C H -0.3020(15) 0.883(7) 0.4991(17) 0.096(13) Uiso 1 1 d . . . H17 H 0.1897(10) 0.112(5) 0.1883(13) 0.055(8) Uiso 1 1 d . . . H18 H 0.1091(10) 0.123(5) 0.2333(12) 0.052(8) Uiso 1 1 d . . . H21 H 0.1421(11) 0.788(5) 0.3784(13) 0.059(9) Uiso 1 1 d . . . H22 H 0.2156(12) 1.073(6) 0.4122(15) 0.078(11) Uiso 1 1 d . . . H23 H 0.2954(11) 1.049(5) 0.3673(13) 0.059(9) Uiso 1 1 d . . . H29 H 0.3994(13) 0.246(7) 0.2572(17) 0.096(12) Uiso 1 1 d . . . H30 H 0.4792(11) 0.236(6) 0.2146(13) 0.064(9) Uiso 1 1 d . . . H32 H 0.4282(10) 0.836(5) 0.0993(13) 0.060(9) Uiso 1 1 d . . . H33 H 0.3501(12) 0.853(6) 0.1491(15) 0.078(11) Uiso 1 1 d . . . H34A H 0.5090(16) 0.647(9) 0.090(2) 0.134(18) Uiso 1 1 d . . . H34B H 0.5446(19) 0.524(9) 0.153(2) 0.15(2) Uiso 1 1 d . . . H35A H 0.480(2) 0.234(10) 0.058(2) 0.16(2) Uiso 1 1 d . . . H35B H 0.5162(18) 0.125(9) 0.118(2) 0.15(2) Uiso 1 1 d . . . H36A H 0.566(2) 0.076(11) 0.037(3) 0.19(3) Uiso 1 1 d . . . H36B H 0.5967(18) 0.282(8) 0.085(2) 0.122(19) Uiso 1 1 d . . . H36C H 0.565(2) 0.380(12) 0.025(3) 0.21(3) Uiso 1 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 C1 0.061(2) 0.068(2) 0.065(2) -0.0122(19) 0.0227(19) 0.0012(19) C2 0.060(2) 0.069(2) 0.075(2) -0.019(2) 0.026(2) -0.009(2) C3 0.0499(18) 0.0503(18) 0.0485(19) 0.0008(15) 0.0126(15) 0.0043(15) C4 0.048(2) 0.058(2) 0.058(2) -0.0059(18) 0.0129(17) -0.0057(17) C5 0.0494(19) 0.059(2) 0.0491(19) 0.0000(17) 0.0170(16) 0.0028(16) C6 0.065(2) 0.071(2) 0.075(3) -0.025(2) 0.025(2) -0.006(2) C7 0.060(2) 0.074(2) 0.089(3) -0.030(2) 0.026(2) -0.017(2) C8 0.0486(19) 0.057(2) 0.056(2) -0.0013(17) 0.0157(16) -0.0010(16) C9 0.053(2) 0.071(2) 0.074(2) -0.010(2) 0.0226(19) -0.0082(19) C10 0.0484(19) 0.071(2) 0.055(2) 0.0048(18) 0.0184(17) 0.0063(17) C11 0.058(2) 0.064(2) 0.065(3) 0.003(2) 0.0216(19) -0.0060(18) C12 0.062(2) 0.067(2) 0.086(3) 0.004(2) 0.034(2) -0.001(2) C13 0.071(3) 0.073(3) 0.108(4) 0.001(3) 0.024(3) 0.008(3) C14 0.058(2) 0.070(2) 0.063(2) -0.0013(18) 0.0177(19) 0.0051(17) C15 0.054(2) 0.066(2) 0.060(2) 0.0010(17) 0.0176(18) 0.0044(16) C16 0.0424(17) 0.0511(18) 0.0471(18) -0.0004(16) 0.0121(15) 0.0032(15) C17 0.053(2) 0.058(2) 0.054(2) -0.0064(17) 0.0137(17) 0.0033(17) C18 0.0476(19) 0.059(2) 0.061(2) -0.0015(18) 0.0132(17) -0.0040(17) C19 0.0469(18) 0.059(2) 0.052(2) 0.0077(17) 0.0159(16) 0.0079(16) C20 0.0517(19) 0.0544(19) 0.0458(19) 0.0056(16) 0.0156(15) 0.0091(16) C21 0.060(2) 0.070(2) 0.053(2) 0.0016(18) 0.0230(18) 0.014(2) C22 0.072(3) 0.063(2) 0.054(2) -0.0073(19) 0.018(2) 0.007(2) C23 0.065(2) 0.059(2) 0.053(2) -0.0012(17) 0.0152(18) -0.0037(18) C24 0.0558(19) 0.0475(18) 0.0420(18) 0.0022(15) 0.0141(15) 0.0026(16) C25 0.0487(18) 0.0449(18) 0.0432(18) 0.0051(15) 0.0108(15) 0.0071(15) C26 0.060(2) 0.056(2) 0.0465(19) 0.0029(16) 0.0148(16) -0.0039(17) C27 0.053(2) 0.059(2) 0.054(2) -0.0070(17) 0.0144(17) 0.0045(17) C28 0.0449(18) 0.056(2) 0.053(2) -0.0035(17) 0.0143(16) 0.0034(16) C29 0.065(2) 0.065(2) 0.070(2) 0.0091(19) 0.023(2) 0.0058(19) C30 0.054(2) 0.070(2) 0.082(3) 0.006(2) 0.016(2) 0.0173(19) C31 0.0487(19) 0.057(2) 0.064(2) -0.0085(18) 0.0148(17) -0.0037(16) C32 0.059(2) 0.063(2) 0.066(2) 0.0086(19) 0.0263(18) 0.0027(18) C33 0.053(2) 0.064(2) 0.065(2) 0.0103(19) 0.0168(18) 0.0097(18) C34 0.057(2) 0.078(3) 0.101(3) -0.019(3) 0.036(2) -0.004(2) C35 0.086(3) 0.086(3) 0.116(4) -0.028(3) 0.055(3) -0.009(3) C36 0.079(3) 0.128(5) 0.107(4) -0.032(4) 0.046(3) -0.003(3) N1 0.0447(15) 0.0596(16) 0.0516(16) -0.0065(13) 0.0164(13) -0.0015(13) O1 0.0559(13) 0.0733(15) 0.0657(14) -0.0114(12) 0.0271(11) -0.0041(11) O2 0.0757(16) 0.0852(17) 0.0714(16) -0.0162(13) 0.0250(13) -0.0249(14) O3 0.0657(15) 0.0924(18) 0.0831(17) -0.0374(15) 0.0295(13) -0.0081(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.356(4) . ? C1 C10 1.406(4) . ? C1 H1 0.96(3) . ? C2 C3 1.415(4) . ? C2 H2 0.94(3) . ? C3 C8 1.405(4) . ? C3 C4 1.413(4) . ? C4 C5 1.364(4) . ? C4 H4 0.94(3) . ? C5 O1 1.364(3) . ? C5 C6 1.404(4) . ? C6 C7 1.352(4) . ? C6 H6 0.93(3) . ? C7 C8 1.413(4) . ? C7 H7 1.00(3) . ? C8 C9 1.412(4) . ? C9 C10 1.373(4) . ? C9 H9 0.96(3) . ? C10 C14 1.437(4) . ? C11 O1 1.442(4) . ? C11 C12 1.503(5) . ? C11 H11A 1.09(3) . ? C11 H11B 0.98(3) . ? C12 C13 1.506(5) . ? C12 H12A 1.01(4) . ? C12 H12B 1.00(3) . ? C13 H13A 1.00(4) . ? C13 H13B 0.94(5) . ? C13 H13C 0.99(4) . ? C14 C15 1.199(4) . ? C15 C19 1.427(4) . ? C16 C17 1.370(4) . ? C16 C25 1.417(4) . ? C16 C27 1.472(4) . ? C17 C18 1.396(4) . ? C17 H17 0.98(3) . ? C18 C19 1.384(4) . ? C18 H18 0.99(3) . ? C19 C20 1.427(4) . ? C20 C21 1.416(4) . ? C20 C25 1.417(4) . ? C21 C22 1.358(4) . ? C21 H21 0.96(3) . ? C22 C23 1.399(4) . ? C22 H22 0.97(3) . ? C23 C24 1.380(4) . ? C23 H23 0.99(3) . ? C24 C25 1.406(4) . ? C24 C26 1.474(4) . ? C26 O2 1.220(3) . ? C26 N1 1.403(4) . ? C27 O3 1.220(3) . ? C27 N1 1.398(4) . ? C28 C33 1.369(4) . ? C28 C29 1.371(4) . ? C28 N1 1.454(3) . ? C29 C30 1.382(4) . ? C29 H29 1.00(4) . ? C30 C31 1.383(4) . ? C30 H30 0.94(3) . ? C31 C32 1.377(4) . ? C31 C34 1.515(4) . ? C32 C33 1.380(4) . ? C32 H32 1.03(3) . ? C33 H33 0.93(3) . ? C34 C35 1.494(5) . ? C34 H34A 1.01(4) . ? C34 H34B 0.95(5) . ? C35 C36 1.523(6) . ? C35 H35A 0.98(5) . ? C35 H35B 0.99(5) . ? C36 H36A 0.97(6) . ? C36 H36B 0.91(4) . ? C36 H36C 1.01(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 C2 C1 C10 120.4(3) . . ? C2 C1 H1 119.5(19) . . ? C10 C1 H1 120.1(19) . . ? C1 C2 C3 122.0(3) . . ? C1 C2 H2 122.4(18) . . ? C3 C2 H2 115.6(18) . . ? C8 C3 C4 120.2(3) . . ? C8 C3 C2 117.8(3) . . ? C4 C3 C2 122.0(3) . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 122.0(16) . . ? C3 C4 H4 117.5(16) . . ? O1 C5 C4 125.5(3) . . ? O1 C5 C6 114.9(3) . . ? C4 C5 C6 119.6(3) . . ? C7 C6 C5 121.0(3) . . ? C7 C6 H6 121.5(19) . . ? C5 C6 H6 117.3(19) . . ? C6 C7 C8 121.2(3) . . ? C6 C7 H7 119.9(18) . . ? C8 C7 H7 118.8(18) . . ? C3 C8 C9 119.4(3) . . ? C3 C8 C7 117.8(3) . . ? C9 C8 C7 122.8(3) . . ? C10 C9 C8 121.4(3) . . ? C10 C9 H9 122(2) . . ? C8 C9 H9 116.1(19) . . ? C9 C10 C1 119.0(3) . . ? C9 C10 C14 121.3(3) . . ? C1 C10 C14 119.8(3) . . ? O1 C11 C12 108.4(3) . . ? O1 C11 H11A 107.8(17) . . ? C12 C11 H11A 110.6(17) . . ? O1 C11 H11B 107.1(17) . . ? C12 C11 H11B 112.7(17) . . ? H11A C11 H11B 110(3) . . ? C11 C12 C13 113.5(3) . . ? C11 C12 H12A 108(2) . . ? C13 C12 H12A 111(2) . . ? C11 C12 H12B 107.8(17) . . ? C13 C12 H12B 108.3(17) . . ? H12A C12 H12B 108(3) . . ? C12 C13 H13A 109(2) . . ? C12 C13 H13B 117(3) . . ? H13A C13 H13B 102(3) . . ? C12 C13 H13C 106(2) . . ? H13A C13 H13C 104(3) . . ? H13B C13 H13C 118(4) . . ? C15 C14 C10 178.0(4) . . ? C14 C15 C19 179.3(3) . . ? C17 C16 C25 119.8(3) . . ? C17 C16 C27 119.8(3) . . ? C25 C16 C27 120.4(3) . . ? C16 C17 C18 120.9(3) . . ? C16 C17 H17 118.8(15) . . ? C18 C17 H17 120.3(15) . . ? C19 C18 C17 121.0(3) . . ? C19 C18 H18 118.7(15) . . ? C17 C18 H18 120.2(15) . . ? C18 C19 C20 119.4(3) . . ? C18 C19 C15 120.0(3) . . ? C20 C19 C15 120.6(3) . . ? C21 C20 C25 117.8(3) . . ? C21 C20 C19 123.3(3) . . ? C25 C20 C19 118.9(3) . . ? C22 C21 C20 121.7(3) . . ? C22 C21 H21 121.4(17) . . ? C20 C21 H21 116.8(17) . . ? C21 C22 C23 120.2(3) . . ? C21 C22 H22 121.4(18) . . ? C23 C22 H22 118.3(18) . . ? C24 C23 C22 120.2(3) . . ? C24 C23 H23 118.6(16) . . ? C22 C23 H23 121.1(16) . . ? C23 C24 C25 120.2(3) . . ? C23 C24 C26 119.4(3) . . ? C25 C24 C26 120.4(3) . . ? C24 C25 C20 119.9(3) . . ? C24 C25 C16 120.2(3) . . ? C20 C25 C16 119.9(3) . . ? O2 C26 N1 119.9(3) . . ? O2 C26 C24 122.6(3) . . ? N1 C26 C24 117.5(3) . . ? O3 C27 N1 120.3(3) . . ? O3 C27 C16 122.4(3) . . ? N1 C27 C16 117.4(3) . . ? C33 C28 C29 120.2(3) . . ? C33 C28 N1 120.4(3) . . ? C29 C28 N1 119.4(3) . . ? C28 C29 C30 119.1(3) . . ? C28 C29 H29 118.2(19) . . ? C30 C29 H29 122.6(19) . . ? C29 C30 C31 122.1(3) . . ? C29 C30 H30 116.3(17) . . ? C31 C30 H30 121.5(17) . . ? C32 C31 C30 116.9(3) . . ? C32 C31 C34 122.0(3) . . ? C30 C31 C34 121.1(3) . . ? C31 C32 C33 121.9(3) . . ? C31 C32 H32 117.9(15) . . ? C33 C32 H32 120.2(15) . . ? C28 C33 C32 119.6(3) . . ? C28 C33 H33 118.0(19) . . ? C32 C33 H33 122.3(19) . . ? C35 C34 C31 113.8(3) . . ? C35 C34 H34A 107(3) . . ? C31 C34 H34A 106(2) . . ? C35 C34 H34B 109(3) . . ? C31 C34 H34B 111(3) . . ? H34A C34 H34B 110(4) . . ? C34 C35 C36 114.3(4) . . ? C34 C35 H35A 109(3) . . ? C36 C35 H35A 115(3) . . ? C34 C35 H35B 106(3) . . ? C36 C35 H35B 108(3) . . ? H35A C35 H35B 103(4) . . ? C35 C36 H36A 110(3) . . ? C35 C36 H36B 111(3) . . ? H36A C36 H36B 116(4) . . ? C35 C36 H36C 109(3) . . ? H36A C36 H36C 110(5) . . ? H36B C36 H36C 100(4) . . ? C27 N1 C26 124.1(2) . . ? C27 N1 C28 117.7(2) . . ? C26 N1 C28 118.2(2) . . ? C5 O1 C11 117.3(2) . . ?