# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_x1n1_angelo_120k _audit_creation_date 2011-09-02T09:43:15-00:00 _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_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H32 N4, 2(C4 H F6 O4)' _chemical_formula_sum 'C40 H34 F12 N4 O8' _chemical_formula_weight 926.71 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7040(3) _cell_length_b 10.8569(3) _cell_length_c 11.5890(4) _cell_angle_alpha 100.578(3) _cell_angle_beta 103.072(3) _cell_angle_gamma 96.793(3) _cell_volume 1033.93(6) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6839 _cell_measurement_theta_min 1.9314 _cell_measurement_theta_max 29.5066 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 474 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.139 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89485 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.34 (release 07-07-2010 CrysAlis171 .NET) (compiled Jul 7 2010,16:04:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.4186 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17165 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_unetI/netI 0.0294 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 29.57 _diffrn_reflns_theta_full 29.50 _diffrn_measured_fraction_theta_max 0.89 _diffrn_measured_fraction_theta_full 0.98 _reflns_number_total 5138 _reflns_number_gt 3761 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+0.5435P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5138 _refine_ls_number_parameters 320 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1484 _refine_ls_wR_factor_gt 0.1299 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.499 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.046 _iucr_refine_instructions_details ; TITL x1n1_angelo in P -1 CELL 0.71073 8.7040 10.8569 11.5890 100.578 103.072 96.793 ZERR 1.00 0.0003 0.0003 0.0004 0.003 0.003 0.003 LATT 1 SFAC C 2.31000 20.84392 1.02000 10.20751 1.58860 0.56870 = 0.86500 51.65125 0.21560 0.003 0.002 11.500 0.770 12.011 SFAC H 0.49300 10.51091 0.32291 26.12573 0.14019 3.14236 = 0.04081 57.79977 0.00304 0.000 0.000 0.620 0.320 1.008 SFAC F 3.53920 10.28251 2.64120 4.29440 1.51700 0.26150 = 1.02430 26.14763 0.27760 0.017 0.010 51.500 0.640 18.998 SFAC N 12.21261 0.00570 3.13220 9.89331 2.01250 28.99754 = 1.16630 0.58260 -11.52901 0.006 0.003 19.600 0.700 14.007 SFAC O 3.04850 13.27711 2.28680 5.70111 1.54630 0.32390 = 0.86700 32.90894 0.25080 0.011 0.006 32.500 0.660 15.999 UNIT 40 34 12 4 8 MERG 2 EADP C7A C7B EADP C8A C8B EADP O3A O3B EADP F4A F4B EADP F5A F5B EADP F6A F6B F6C SUMP 1.00000 0.00001 1.0 7 1.0 8 1.0 9 FMAP 2 PLAN 10 ACTA 59.00 L.S. 4 WGHT 0.057000 0.539200 FVAR 7.27403 0.71766 0.65365 0.52135 0.85787 0.85527 0.45527 FVAR 0.32151 0.22322 C1 1 0.169191 0.735865 0.137004 11.00000 0.03065 0.02598 = 0.03234 0.01406 0.01314 0.00703 C2 1 0.012829 0.661168 0.110055 11.00000 0.03068 0.02456 = 0.03382 0.01185 0.01620 0.00640 C3 1 -0.007393 0.563010 0.172524 11.00000 0.03694 0.02595 = 0.03527 0.01208 0.02034 0.00842 C4 1 0.268998 0.605840 0.275815 11.00000 0.04292 0.02873 = 0.02731 0.01051 0.01262 0.01194 C5 1 0.298566 0.703054 0.216885 11.00000 0.03277 0.02806 = 0.03192 0.01247 0.00810 0.00614 C6 1 0.396109 0.569227 0.366862 11.00000 0.05580 0.03891 = 0.03549 0.01806 0.00523 0.01326 AFIX 3 H6A 2 0.376145 0.481456 0.366079 11.00000 -1.20000 H6B 2 0.369923 0.594626 0.443113 11.00000 -1.20000 AFIX 0 C7A 1 0.557826 0.609270 0.354910 21.00000 0.04453 0.06122 = 0.04267 0.02708 0.00183 0.01563 C7B 1 0.558145 0.671466 0.408241 -21.00000 0.04453 0.06122 = 0.04267 0.02708 0.00183 0.01563 AFIX 3 H7A 2 0.628263 0.604459 0.429966 11.00000 -1.20000 H7B 2 0.575025 0.565066 0.276476 11.00000 -1.20000 AFIX 0 C8A 1 0.578710 0.748960 0.353365 31.00000 0.04151 0.06530 = 0.04962 0.02813 -0.00945 -0.00930 C8B 1 0.598400 0.716676 0.300305 -31.00000 0.04151 0.06530 = 0.04962 0.02813 -0.00945 -0.00930 AFIX 3 H8A 2 0.684808 0.767928 0.339365 11.00000 -1.20000 H8B 2 0.549875 0.795604 0.431585 11.00000 -1.20000 AFIX 0 C9 1 0.466002 0.771946 0.238555 11.00000 0.03433 0.04140 = 0.05124 0.02451 0.00241 0.00188 AFIX 3 H9A 2 0.499075 0.762329 0.163081 11.00000 -1.20000 H9B 2 0.465637 0.856564 0.255381 11.00000 -1.20000 AFIX 0 C10 1 -0.156231 0.482259 0.148249 11.00000 0.04277 0.02851 = 0.05629 0.01887 0.02645 0.00557 AFIX 43 H10 2 -0.168773 0.419545 0.191875 11.00000 -1.20000 AFIX 0 C11 1 -0.281711 0.497865 0.059420 11.00000 0.03517 0.03739 = 0.06695 0.01658 0.01959 -0.00041 AFIX 43 H11 2 -0.380423 0.446044 0.043608 11.00000 -1.20000 AFIX 0 C12 1 -0.263075 0.590207 -0.007232 11.00000 0.02994 0.03362 = 0.04450 0.00773 0.01156 0.00363 AFIX 43 H12 2 -0.348162 0.596881 -0.069521 11.00000 -1.20000 AFIX 0 C13 1 -0.120575 0.671904 0.017588 11.00000 0.02991 0.03041 = 0.03963 0.01592 0.01149 0.00496 AFIX 43 H13 2 -0.111341 0.734695 -0.026444 11.00000 -1.20000 AFIX 0 C14 1 0.095541 0.915873 0.040736 11.00000 0.02540 0.02773 = 0.04196 0.02031 0.00663 0.00012 C15 1 0.003868 0.971328 0.112189 11.00000 0.03507 0.03622 = 0.03463 0.02079 0.00984 0.00428 AFIX 43 H15 2 0.007046 0.952303 0.187648 11.00000 -1.20000 AFIX 0 C16 1 0.092554 0.944886 -0.071324 11.00000 0.03253 0.03265 = 0.03911 0.01646 0.01405 0.00448 AFIX 43 H16 2 0.155115 0.908172 -0.118832 11.00000 -1.20000 AFIX 0 C17 1 0.455929 0.191162 0.258303 11.00000 0.05820 0.03360 = 0.05380 0.00345 0.01555 0.00929 C18 1 0.505613 0.149000 0.141245 11.00000 0.03080 0.02966 = 0.04689 0.01205 0.01019 0.00233 C19 1 -0.058846 0.174021 0.447786 11.00000 0.07198 0.03587 = 0.04571 0.01818 0.01872 0.00240 C20 1 -0.013011 0.310174 0.432207 11.00000 0.05472 0.03275 = 0.03455 0.01249 0.01725 0.00249 N1 4 0.199985 0.833287 0.083324 11.00000 0.02403 0.04029 = 0.05726 0.03308 0.01337 0.00559 AFIX 3 H1 2 0.297199 0.861143 0.090031 11.00000 -1.20000 AFIX 0 N2 4 0.120843 0.541222 0.253977 11.00000 0.04231 0.02725 = 0.03169 0.01605 0.01856 0.00925 AFIX 3 H2 2 0.101247 0.478029 0.291233 11.00000 -1.20000 AFIX 0 O1 5 0.475440 0.029495 0.100157 11.00000 0.04425 0.02849 = 0.03976 0.00712 0.01807 -0.00395 O2 5 0.564384 0.229603 0.097791 11.00000 0.07186 0.03322 = 0.08677 0.01960 0.04058 -0.00143 O3A 5 -0.079341 0.396025 0.493422 41.00000 0.08800 0.03026 = 0.05043 0.00523 0.04134 0.00177 O3B 5 0.008667 0.386011 0.528231 -41.00000 0.08800 0.03026 = 0.05043 0.00523 0.04134 0.00177 O4 5 0.039258 0.324357 0.348542 11.00000 0.12750 0.03971 = 0.07784 0.03482 0.07247 0.03418 F1 3 0.562641 0.286074 0.333375 11.00000 0.09405 0.05875 = 0.06444 -0.01760 0.00175 0.00428 F2 3 0.317769 0.234987 0.233505 11.00000 0.06475 0.08483 = 0.08012 0.00583 0.03177 0.03213 F3 3 0.436475 0.100708 0.317788 11.00000 0.15384 0.05681 = 0.05889 0.01809 0.06313 0.02850 F4A 3 -0.171826 0.105761 0.351003 51.00000 0.07672 0.04726 = 0.06742 0.01408 0.01032 -0.01735 F4B 3 -0.196651 0.133816 0.412733 -51.00000 0.07672 0.04726 = 0.06742 0.01408 0.01032 -0.01735 F5A 3 0.062315 0.109280 0.440953 61.00000 0.08377 0.04001 = 0.10416 0.02834 0.02173 0.01712 F5B 3 0.042784 0.132563 0.503802 -61.00000 0.08377 0.04001 = 0.10416 0.02834 0.02173 0.01712 F6A 3 -0.114081 0.162127 0.542647 71.00000 0.10354 0.04927 = 0.05659 0.02833 0.04131 0.00031 F6B 3 -0.037087 0.176977 0.567091 81.00000 0.10354 0.04927 = 0.05659 0.02833 0.04131 0.00031 F6C 3 -0.176947 0.175403 0.517093 91.00000 0.10354 0.04927 = 0.05659 0.02833 0.04131 0.00031 H1A 2 0.500000 0.000000 0.000000 10.50000 0.09799 H3A 2 10.000000 10.500000 10.500000 10.50000 0.15337 HKLF 4 REM x1n1_angelo in P -1 REM R1 = 0.0541 for 3761 Fo > 4sig(Fo) and 0.0773 for all 5138 data REM 320 parameters refined using 1 restraints END WGHT 0.0571 0.5378 REM Highest difference peak 0.499, deepest hole -0.276, 1-sigma level 0.046 Q1 1 -0.2990 0.5532 0.1204 11.00000 0.05 0.50 Q2 1 -0.0489 0.0837 0.3727 11.00000 0.05 0.34 Q3 1 0.1034 0.3578 0.4126 11.00000 0.05 0.33 Q4 1 0.4777 0.1601 0.2002 11.00000 0.05 0.28 Q5 1 0.0005 0.6122 0.1460 11.00000 0.05 0.26 Q6 1 -0.0295 0.2417 0.4381 11.00000 0.05 0.25 Q7 1 0.2896 0.6482 0.2367 11.00000 0.05 0.25 Q8 1 0.3589 0.2296 0.3129 11.00000 0.05 0.25 Q9 1 -0.1137 0.3938 0.4399 11.00000 0.05 0.23 Q10 1 -0.2299 0.1817 0.4590 11.00000 0.05 0.23 ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.017 0.01 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1692(2) 0.73587(15) 0.13700(15) 0.0276(3) Uani 1 1 d . . . C2 C 0.0128(2) 0.66117(15) 0.11005(15) 0.0275(3) Uani 1 1 d . . . C3 C -0.0074(2) 0.56301(15) 0.17252(16) 0.0299(4) Uani 1 1 d . . . C4 C 0.2690(2) 0.60584(16) 0.27581(15) 0.0313(4) Uani 1 1 d . . . C5 C 0.2986(2) 0.70305(16) 0.21689(16) 0.0301(4) Uani 1 1 d . . . C6 C 0.3961(3) 0.56923(19) 0.36686(18) 0.0427(5) Uani 1 1 d . . . H6A H 0.3761 0.4815 0.3661 0.051 Uiso 1 1 d R . . H6B H 0.3699 0.5946 0.4431 0.051 Uiso 1 1 d R . . C7A C 0.5578(4) 0.6093(4) 0.3549(3) 0.0483(9) Uani 0.718(6) 1 d P . . C7B C 0.5581(9) 0.6715(9) 0.4082(8) 0.0483(9) Uani 0.282(6) 1 d P . . H7A H 0.6283 0.6045 0.4300 0.058 Uiso 1 1 d R . . H7B H 0.5750 0.5651 0.2765 0.058 Uiso 1 1 d R . . C8A C 0.5787(5) 0.7490(5) 0.3534(5) 0.0551(13) Uani 0.654(9) 1 d P . . C8B C 0.5984(10) 0.7167(9) 0.3003(9) 0.0551(13) Uani 0.346(9) 1 d P . . H8A H 0.6848 0.7679 0.3394 0.066 Uiso 1 1 d R . . H8B H 0.5499 0.7956 0.4316 0.066 Uiso 1 1 d R . . C9 C 0.4660(2) 0.77195(19) 0.23856(19) 0.0422(5) Uani 1 1 d . . . H9A H 0.4991 0.7623 0.1631 0.051 Uiso 1 1 d R . . H9B H 0.4656 0.8566 0.2554 0.051 Uiso 1 1 d R . . C10 C -0.1562(2) 0.48226(17) 0.14825(19) 0.0390(4) Uani 1 1 d . . . H10 H -0.1688 0.4195 0.1919 0.047 Uiso 1 1 calc R . . C11 C -0.2817(2) 0.49787(19) 0.0594(2) 0.0453(5) Uani 1 1 d . . . H11 H -0.3804 0.4460 0.0436 0.054 Uiso 1 1 calc R . . C12 C -0.2631(2) 0.59021(17) -0.00723(18) 0.0359(4) Uani 1 1 d . . . H12 H -0.3482 0.5969 -0.0695 0.043 Uiso 1 1 calc R . . C13 C -0.1206(2) 0.67190(16) 0.01759(17) 0.0318(4) Uani 1 1 d . . . H13 H -0.1113 0.7347 -0.0264 0.038 Uiso 1 1 calc R . . C14 C 0.0955(2) 0.91587(16) 0.04074(16) 0.0307(4) Uani 1 1 d . . . C15 C 0.0039(2) 0.97133(17) 0.11219(17) 0.0335(4) Uani 1 1 d . . . H15 H 0.0070 0.9523 0.1876 0.040 Uiso 1 1 calc R . . C16 C 0.0926(2) 0.94489(17) -0.07132(17) 0.0329(4) Uani 1 1 d . . . H16 H 0.1551 0.9082 -0.1188 0.039 Uiso 1 1 calc R . . C17 C 0.4559(3) 0.19116(19) 0.2583(2) 0.0490(5) Uani 1 1 d . . . C18 C 0.5056(2) 0.14900(17) 0.14124(18) 0.0355(4) Uani 1 1 d . . . C19 C -0.0588(3) 0.1740(2) 0.4478(2) 0.0499(5) Uani 1 1 d . . . C20 C -0.0130(3) 0.31017(18) 0.43221(17) 0.0394(4) Uani 1 1 d . . . N1 N 0.19998(18) 0.83329(15) 0.08332(15) 0.0370(4) Uani 1 1 d . . . H1 H 0.2972 0.8611 0.0900 0.044 Uiso 1 1 d R . . N2 N 0.12084(18) 0.54122(13) 0.25398(13) 0.0307(3) Uani 1 1 d . . . H2 H 0.1012 0.4780 0.2912 0.037 Uiso 1 1 d R . . O1 O 0.47544(16) 0.02949(11) 0.10016(12) 0.0372(3) Uani 1 1 d . . . O2 O 0.5644(2) 0.22960(14) 0.09779(17) 0.0606(5) Uani 1 1 d . . . O3A O -0.0793(6) 0.3960(4) 0.4934(4) 0.0535(9) Uani 0.521(5) 1 d P . . O3B O 0.0087(7) 0.3860(4) 0.5282(4) 0.0535(9) Uani 0.479(5) 1 d P . . O4 O 0.0393(3) 0.32436(15) 0.34854(17) 0.0694(6) Uani 1 1 d . . . F1 F 0.5626(2) 0.28607(14) 0.33337(14) 0.0803(5) Uani 1 1 d . . . F2 F 0.31777(19) 0.23499(16) 0.23350(15) 0.0743(5) Uani 1 1 d . . . F3 F 0.4365(3) 0.10071(14) 0.31779(14) 0.0822(6) Uani 1 1 d . . . F4A F -0.1718(2) 0.10576(19) 0.3510(3) 0.0672(7) Uani 0.858(6) 1 d P . . F4B F -0.1967(17) 0.1338(12) 0.4127(17) 0.0672(7) Uani 0.142(6) 1 d P . . F5A F 0.0623(3) 0.1093(2) 0.4410(4) 0.0741(9) Uani 0.855(9) 1 d P . . F5B F 0.043(2) 0.1326(14) 0.504(2) 0.0741(9) Uani 0.145(9) 1 d P . . F6A F -0.114(2) 0.1621(7) 0.5426(8) 0.065(3) Uani 0.455(4) 1 d P . . F6B F -0.0371(18) 0.1770(8) 0.5671(9) 0.065(3) Uani 0.322(10) 1 d P . . F6C F -0.1769(19) 0.1754(13) 0.5171(12) 0.065(3) Uani 0.223(10) 1 d P . . H1A H 0.5000 0.0000 0.0000 0.098(14) Uiso 1 2 d S . . H3A H 0.0000 0.5000 0.5000 0.15(2) Uiso 1 2 d S . . 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 0.0307(9) 0.0260(8) 0.0323(9) 0.0141(7) 0.0131(7) 0.0070(6) C2 0.0307(9) 0.0246(8) 0.0338(9) 0.0118(7) 0.0162(7) 0.0064(6) C3 0.0369(9) 0.0260(8) 0.0353(9) 0.0121(7) 0.0203(7) 0.0084(7) C4 0.0429(10) 0.0287(8) 0.0273(8) 0.0105(7) 0.0126(7) 0.0119(7) C5 0.0328(9) 0.0281(8) 0.0319(9) 0.0125(7) 0.0081(7) 0.0061(7) C6 0.0558(13) 0.0389(10) 0.0355(10) 0.0181(8) 0.0052(9) 0.0133(9) C7A 0.0445(14) 0.061(2) 0.0427(19) 0.0271(16) 0.0018(14) 0.0156(15) C7B 0.0445(14) 0.061(2) 0.0427(19) 0.0271(16) 0.0018(14) 0.0156(15) C8A 0.0415(17) 0.065(3) 0.050(3) 0.028(2) -0.0095(19) -0.0093(16) C8B 0.0415(17) 0.065(3) 0.050(3) 0.028(2) -0.0095(19) -0.0093(16) C9 0.0343(10) 0.0414(10) 0.0512(12) 0.0245(9) 0.0024(9) 0.0019(8) C10 0.0428(11) 0.0285(9) 0.0563(12) 0.0189(8) 0.0265(9) 0.0056(8) C11 0.0352(10) 0.0374(10) 0.0670(14) 0.0166(10) 0.0196(10) -0.0004(8) C12 0.0299(9) 0.0336(9) 0.0445(10) 0.0077(8) 0.0116(8) 0.0036(7) C13 0.0299(9) 0.0304(9) 0.0396(10) 0.0159(7) 0.0115(7) 0.0050(7) C14 0.0254(8) 0.0277(8) 0.0420(10) 0.0203(7) 0.0066(7) 0.0001(6) C15 0.0351(9) 0.0362(9) 0.0346(9) 0.0208(7) 0.0098(7) 0.0043(7) C16 0.0325(9) 0.0326(9) 0.0391(10) 0.0165(7) 0.0140(7) 0.0045(7) C17 0.0582(13) 0.0336(10) 0.0538(13) 0.0034(9) 0.0155(10) 0.0093(9) C18 0.0308(9) 0.0297(9) 0.0469(11) 0.0121(8) 0.0102(8) 0.0023(7) C19 0.0720(16) 0.0359(11) 0.0457(12) 0.0182(9) 0.0187(11) 0.0024(10) C20 0.0547(12) 0.0328(9) 0.0346(10) 0.0125(8) 0.0173(9) 0.0025(8) N1 0.0240(7) 0.0403(8) 0.0573(10) 0.0331(8) 0.0134(7) 0.0056(6) N2 0.0423(9) 0.0272(7) 0.0317(7) 0.0161(6) 0.0186(6) 0.0092(6) O1 0.0442(8) 0.0285(6) 0.0398(7) 0.0071(5) 0.0181(6) -0.0039(5) O2 0.0719(11) 0.0332(8) 0.0868(12) 0.0196(8) 0.0406(10) -0.0014(7) O3A 0.088(3) 0.0303(10) 0.050(2) 0.0052(12) 0.041(2) 0.0018(19) O3B 0.088(3) 0.0303(10) 0.050(2) 0.0052(12) 0.041(2) 0.0018(19) O4 0.1275(16) 0.0397(8) 0.0778(12) 0.0348(8) 0.0725(12) 0.0342(9) F1 0.0940(12) 0.0587(9) 0.0644(9) -0.0176(7) 0.0017(8) 0.0043(8) F2 0.0647(9) 0.0848(11) 0.0801(11) 0.0058(8) 0.0318(8) 0.0321(8) F3 0.1538(17) 0.0568(9) 0.0589(9) 0.0181(7) 0.0631(10) 0.0285(10) F4A 0.0767(12) 0.0473(10) 0.0674(17) 0.0141(10) 0.0103(11) -0.0173(8) F4B 0.0767(12) 0.0473(10) 0.0674(17) 0.0141(10) 0.0103(11) -0.0173(8) F5A 0.0838(13) 0.0400(9) 0.104(3) 0.0283(13) 0.0217(14) 0.0171(8) F5B 0.0838(13) 0.0400(9) 0.104(3) 0.0283(13) 0.0217(14) 0.0171(8) F6A 0.104(8) 0.0493(14) 0.057(3) 0.0283(16) 0.041(5) 0.000(3) F6B 0.104(8) 0.0493(14) 0.057(3) 0.0283(16) 0.041(5) 0.000(3) F6C 0.104(8) 0.0493(14) 0.057(3) 0.0283(16) 0.041(5) 0.000(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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F4A C19 1.340(4) . . yes F4B C19 1.176(17) . . yes F5A C19 1.344(4) . . yes F5B C19 1.161(19) . . yes F6A C19 1.315(12) . . yes F6B C19 1.344(10) . . yes F6C C19 1.439(16) . . yes F1 C17 1.327(3) . . yes F2 C17 1.336(3) . . yes F3 C17 1.315(3) . . yes O3A C20 1.333(6) . . yes O3B C20 1.218(5) . . yes O4 C20 1.187(3) . . yes O3A H3A 1.2300 . . no O3B H3A 1.3400 . . no O1 C18 1.271(2) . . yes O2 C18 1.206(3) . . yes O1 H1A 1.2200 . . no N1 C1 1.352(2) . . yes N1 C14 1.424(2) . . yes N2 C3 1.364(2) . . yes N2 C4 1.339(2) . . yes N1 H1 0.8500 . . no N2 H2 0.8900 . . no C1 C5 1.413(2) . . no C1 C2 1.436(2) . . no C2 C13 1.423(3) . . no C2 C3 1.410(2) . . no C3 C10 1.415(3) . . no C4 C5 1.388(2) . . no C4 C6 1.492(3) . . no C5 C9 1.501(3) . . no C6 C7B 1.612(9) . . no C6 C7A 1.468(5) . . no C8A C9 1.546(6) . . no C8B C9 1.463(10) . . no C10 C11 1.372(3) . . no C11 C12 1.390(3) . . no C12 C13 1.376(3) . . no C14 C16 1.387(3) . . no C14 C15 1.383(3) . . no C15 C16 1.384(3) . 2_575 no C6 H6A 0.9500 . . no C6 H6B 0.9600 . . no C7A H7A 0.9600 . . no C7A H7B 0.9900 . . no C7B H8B 1.3400 . . no C7B H7A 1.0300 . . no C8A H8A 0.9800 . . no C8A H8B 1.0600 . . no C8B H8A 0.8600 . . no C9 H9A 0.9700 . . no C9 H9B 0.9000 . . no C10 H10 0.9300 . . no C11 H11 0.9300 . . no C12 H12 0.9300 . . no C13 H13 0.9300 . . no C15 H15 0.9300 . . no C16 H16 0.9300 . . no C19 C20 1.540(3) . . no C17 C18 1.524(3) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 O3A H3A 106.00 . . . no C20 O3B H3A 106.00 . . . no C18 O1 H1A 112.00 . . . no C1 N1 C14 128.45(16) . . . yes C3 N2 C4 123.41(15) . . . yes C14 N1 H1 113.00 . . . no C1 N1 H1 117.00 . . . no C4 N2 H2 121.00 . . . no C3 N2 H2 116.00 . . . no N1 C1 C5 118.05(16) . . . yes C2 C1 C5 119.56(15) . . . no N1 C1 C2 122.30(16) . . . yes C3 C2 C13 117.22(16) . . . no C1 C2 C3 117.87(15) . . . no C1 C2 C13 124.70(15) . . . no C2 C3 C10 121.42(17) . . . no N2 C3 C10 119.04(16) . . . yes N2 C3 C2 119.47(16) . . . yes C5 C4 C6 122.95(17) . . . no N2 C4 C6 116.61(16) . . . yes N2 C4 C5 120.43(16) . . . yes C1 C5 C4 119.03(16) . . . no C4 C5 C9 120.09(16) . . . no C1 C5 C9 120.89(16) . . . no C4 C6 C7A 112.9(2) . . . no C4 C6 C7B 112.2(4) . . . no C5 C9 C8A 111.9(2) . . . no C5 C9 C8B 118.4(4) . . . no C3 C10 C11 118.99(18) . . . no C10 C11 C12 120.8(2) . . . no C11 C12 C13 120.95(19) . . . no C2 C13 C12 120.56(17) . . . no N1 C14 C15 120.68(17) . . . yes C15 C14 C16 120.31(17) . . . no N1 C14 C16 118.93(16) . . . yes C14 C15 C16 119.97(17) . . 2_575 no C14 C16 C15 119.71(17) . . 2_575 no C4 C6 H6B 105.00 . . . no H6A C6 H6B 94.00 . . . no C7B C6 H6A 132.00 . . . no C4 C6 H6A 112.00 . . . no C7A C6 H6A 112.00 . . . no C7A C6 H6B 120.00 . . . no C7B C6 H6B 92.00 . . . no H7A C7A H7B 120.00 . . . no C6 C7A H7B 112.00 . . . no C6 C7A H7A 105.00 . . . no H7A C7B H8B 144.00 . . . no C6 C7B H7A 93.00 . . . no C6 C7B H8B 120.00 . . . no C9 C8A H8A 103.00 . . . no H8A C8A H8B 121.00 . . . no C9 C8A H8B 110.00 . . . no C9 C8B H8A 117.00 . . . no C8A C9 H9A 120.00 . . . no C5 C9 H9A 110.00 . . . no C8A C9 H9B 104.00 . . . no C5 C9 H9B 109.00 . . . no C8B C9 H9B 121.00 . . . no C8B C9 H9A 94.00 . . . no H9A C9 H9B 101.00 . . . no C11 C10 H10 120.00 . . . no C3 C10 H10 121.00 . . . no C12 C11 H11 120.00 . . . no C10 C11 H11 120.00 . . . no C11 C12 H12 120.00 . . . no C13 C12 H12 120.00 . . . no C2 C13 H13 120.00 . . . no C12 C13 H13 120.00 . . . no C14 C15 H15 120.00 . . . no C16 C15 H15 120.00 2_575 . . no C15 C16 H16 120.00 2_575 . . no C14 C16 H16 120.00 . . . no F4A C19 C20 110.9(2) . . . yes F6A C19 C20 116.7(4) . . . yes F4B C19 C20 114.1(7) . . . yes F5B C19 C20 115.8(9) . . . yes F6C C19 C20 108.1(6) . . . yes F5A C19 C20 109.9(2) . . . yes F6B C19 C20 108.4(5) . . . yes O3A C20 O4 124.7(3) . . . yes O3B C20 C19 110.4(3) . . . yes O4 C20 C19 118.54(19) . . . yes O3B C20 O4 127.1(3) . . . yes O3A C20 C19 113.8(3) . . . yes F1 C17 F2 106.63(19) . . . yes F1 C17 F3 107.55(19) . . . yes F2 C17 F3 107.5(2) . . . yes F2 C17 C18 109.63(18) . . . yes F3 C17 C18 114.29(19) . . . yes F1 C17 C18 111.0(2) . . . yes O1 C18 C17 113.79(17) . . . yes O2 C18 C17 118.24(18) . . . yes O1 C18 O2 127.96(19) . . . yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N1 C1 C2 30.7(3) . . . . no C14 N1 C1 C5 -152.99(18) . . . . no C1 N1 C14 C15 47.0(3) . . . . no C1 N1 C14 C16 -136.1(2) . . . . no C4 N2 C3 C10 174.52(17) . . . . no C3 N2 C4 C5 1.7(3) . . . . no C3 N2 C4 C6 -179.42(17) . . . . no C4 N2 C3 C2 -2.4(3) . . . . no C5 C1 C2 C3 4.8(2) . . . . no C2 C1 C5 C4 -5.5(3) . . . . no N1 C1 C5 C9 -1.8(3) . . . . no N1 C1 C2 C3 -178.94(16) . . . . no N1 C1 C2 C13 6.5(3) . . . . no C5 C1 C2 C13 -169.70(17) . . . . no N1 C1 C5 C4 178.09(16) . . . . no C2 C1 C5 C9 174.65(16) . . . . no C3 C2 C13 C12 0.9(3) . . . . no C1 C2 C3 N2 -1.0(2) . . . . no C1 C2 C3 C10 -177.78(17) . . . . no C13 C2 C3 N2 173.96(16) . . . . no C13 C2 C3 C10 -2.8(3) . . . . no C1 C2 C13 C12 175.49(17) . . . . no N2 C3 C10 C11 -174.85(18) . . . . no C2 C3 C10 C11 2.0(3) . . . . no N2 C4 C5 C1 2.3(3) . . . . no C6 C4 C5 C9 3.4(3) . . . . no N2 C4 C5 C9 -177.85(17) . . . . no C6 C4 C5 C1 -176.49(17) . . . . no C5 C4 C6 C7A -21.5(3) . . . . no N2 C4 C6 C7A 159.7(2) . . . . no C4 C5 C9 C8A -16.3(3) . . . . no C1 C5 C9 C8A 163.5(3) . . . . no C3 C10 C11 C12 0.9(3) . . . . no C10 C11 C12 C13 -2.8(3) . . . . no C11 C12 C13 C2 1.9(3) . . . . no N1 C14 C15 C16 177.58(17) . . . 2_575 no C16 C14 C15 C16 0.7(3) . . . 2_575 no N1 C14 C16 C15 -177.63(17) . . . 2_575 no C15 C14 C16 C15 -0.7(3) . . . 2_575 no C14 C15 C16 C14 -0.7(3) . . 2_575 2_575 no F4A C19 C20 O3A 101.5(3) . . . . no F4A C19 C20 O4 -59.8(3) . . . . no F5A C19 C20 O3A -148.5(4) . . . . no F5A C19 C20 O4 50.2(4) . . . . no F1 C17 C18 O1 141.55(18) . . . . no F1 C17 C18 O2 -39.8(3) . . . . no F2 C17 C18 O1 -101.0(2) . . . . no F2 C17 C18 O2 77.8(2) . . . . no F3 C17 C18 O1 19.7(3) . . . . no F3 C17 C18 O2 -161.6(2) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1 O1 0.8500 2.2200 2.958(2) 146.00 1_565 yes O1 H1A O1 1.2200 1.2200 2.4392(19) 180.00 2_655 yes N2 H2 O4 0.8900 1.9700 2.856(2) 171.00 1_555 yes O3A H3A O3A 1.2300 1.2300 2.464(7) 180.00 2_566 yes C11 H11 O2 0.9300 2.5600 3.209(3) 127.00 1_455 yes _database_code_depnum_ccdc_archive 'CCDC 945409' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_x2n1_angelo_120k _audit_creation_date 2011-09-01T13:29:29-00:00 _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_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C38 H36 N4, 2(C4 H F6 O4)' _chemical_formula_sum 'C46 H38 F12 N4 O8' _chemical_formula_weight 1002.81 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7578(2) _cell_length_b 11.2552(3) _cell_length_c 11.8308(3) _cell_angle_alpha 115.403(2) _cell_angle_beta 97.181(2) _cell_angle_gamma 106.900(2) _cell_volume 1075.12(5) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 26266 _cell_measurement_theta_min 1.9865 _cell_measurement_theta_max 32.8557 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.549 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 514 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.86011 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.34 (release 07-07-2010 CrysAlis171 .NET) (compiled Jul 7 2010,16:04:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.4186 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 78540 _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 32.93 _diffrn_reflns_theta_full 32.90 _diffrn_measured_fraction_theta_max 0.954 _diffrn_measured_fraction_theta_full 1.000 _reflns_number_total 7672 _reflns_number_gt 5887 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.2464P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7672 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1312 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.419 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.059 _iucr_refine_instructions_details ; TITL x2n1_angelo in P -1 CELL 0.71073 9.7578 11.2552 11.8308 115.403 97.181 106.900 ZERR 1.00 0.0002 0.0003 0.0003 0.002 0.002 0.002 LATT 1 SFAC C 2.31000 20.84392 1.02000 10.20751 1.58860 0.56870 = 0.86500 51.65125 0.21560 0.003 0.002 11.500 0.770 12.011 SFAC H 0.49300 10.51091 0.32291 26.12573 0.14019 3.14236 = 0.04081 57.79977 0.00304 0.000 0.000 0.620 0.320 1.008 SFAC F 3.53920 10.28251 2.64120 4.29440 1.51700 0.26150 = 1.02430 26.14763 0.27760 0.017 0.010 51.500 0.640 18.998 SFAC N 12.21261 0.00570 3.13220 9.89331 2.01250 28.99754 = 1.16630 0.58260 -11.52901 0.006 0.003 19.600 0.700 14.007 SFAC O 3.04850 13.27711 2.28680 5.70111 1.54630 0.32390 = 0.86700 32.90894 0.25080 0.011 0.006 32.500 0.660 15.999 UNIT 46 38 12 4 8 MERG 2 OMIT 0 FMAP 2 PLAN 20 ACTA 65.8 BOND L.S. 4 WGHT 0.067900 0.246400 FVAR 5.16586 C1 1 0.934054 0.721331 0.255940 11.00000 0.01720 0.02130 = 0.01835 0.01021 0.00901 0.00786 C2 1 0.954728 0.588156 0.207612 11.00000 0.02017 0.02105 = 0.01864 0.00980 0.00975 0.00855 C3 1 1.087151 0.584357 0.172342 11.00000 0.02020 0.02355 = 0.01982 0.01090 0.00969 0.00982 C4 1 1.161955 0.823482 0.211750 11.00000 0.01988 0.02263 = 0.02126 0.00969 0.01121 0.00740 C5 1 1.034386 0.834801 0.247273 11.00000 0.01920 0.02024 = 0.02051 0.00987 0.01081 0.00690 C6 1 1.280583 0.941745 0.209616 11.00000 0.02389 0.02379 = 0.03246 0.01066 0.01784 0.00568 AFIX 23 H6A 2 1.273513 0.918946 0.119633 11.00000 -1.20000 H6B 2 1.378265 0.949168 0.248869 11.00000 -1.20000 AFIX 0 C7 1 1.266397 1.084125 0.282575 11.00000 0.02672 0.02162 = 0.03270 0.01142 0.01619 0.00498 AFIX 23 H7A 2 1.297803 1.119383 0.375979 11.00000 -1.20000 H7B 2 1.330295 1.153034 0.263801 11.00000 -1.20000 AFIX 0 C8 1 1.104659 1.065216 0.239983 11.00000 0.02953 0.02285 = 0.03037 0.01439 0.01549 0.00850 AFIX 23 H8A 2 1.071347 1.023420 0.145725 11.00000 -1.20000 H8B 2 1.096514 1.157335 0.279051 11.00000 -1.20000 AFIX 0 C9 1 1.005914 0.968969 0.281949 11.00000 0.02339 0.02199 = 0.02782 0.01330 0.01423 0.00958 AFIX 23 H9A 2 1.023438 1.021214 0.375756 11.00000 -1.20000 H9B 2 0.901802 0.943577 0.240450 11.00000 -1.20000 AFIX 0 C10 1 1.119231 0.460392 0.129126 11.00000 0.02630 0.02872 = 0.02435 0.01228 0.01216 0.01602 AFIX 43 H10 2 1.207989 0.460538 0.108155 11.00000 -1.20000 AFIX 0 C11 1 1.018009 0.339688 0.118406 11.00000 0.03787 0.02603 = 0.02994 0.01346 0.01511 0.01807 AFIX 43 H11 2 1.039838 0.258486 0.093245 11.00000 -1.20000 AFIX 0 C12 1 0.881243 0.338012 0.145274 11.00000 0.03436 0.02261 = 0.02881 0.01298 0.01487 0.01108 AFIX 43 H12 2 0.811222 0.254267 0.133634 11.00000 -1.20000 AFIX 0 C13 1 0.850160 0.458879 0.188530 11.00000 0.02451 0.02073 = 0.02408 0.00975 0.01182 0.00782 AFIX 43 H13 2 0.759058 0.455810 0.205558 11.00000 -1.20000 AFIX 0 C14 1 0.730963 0.670365 0.359979 11.00000 0.01842 0.02058 = 0.02306 0.01226 0.01276 0.00885 C15 1 0.792330 0.632250 0.444749 11.00000 0.01474 0.02404 = 0.02724 0.01454 0.00963 0.00785 AFIX 43 H15 2 0.894270 0.651428 0.465402 11.00000 -1.20000 AFIX 0 C16 1 0.701753 0.565433 0.498905 11.00000 0.01581 0.02231 = 0.02492 0.01448 0.00843 0.00864 AFIX 43 H16 2 0.744164 0.539641 0.555141 11.00000 -1.20000 AFIX 0 C17 1 0.548089 0.535902 0.470954 11.00000 0.01547 0.01847 = 0.02026 0.01029 0.00900 0.00739 C18 1 0.490638 0.579676 0.388462 11.00000 0.01661 0.04202 = 0.03530 0.02805 0.01213 0.01314 AFIX 43 H18 2 0.389465 0.563921 0.369888 11.00000 -1.20000 AFIX 0 C19 1 0.579978 0.646038 0.333287 11.00000 0.01983 0.03967 = 0.03268 0.02699 0.01312 0.01396 AFIX 43 H19 2 0.538663 0.674083 0.278593 11.00000 -1.20000 AFIX 0 C20 1 0.467753 0.297284 -0.030795 11.00000 0.02363 0.03453 = 0.02497 0.01658 0.01106 0.01242 C21 1 0.398132 0.182966 0.006254 11.00000 0.02909 0.04140 = 0.03647 0.02452 0.01346 0.01336 C22 1 1.249539 0.797656 0.592156 11.00000 0.02296 0.02968 = 0.03264 0.01661 0.00965 0.01503 C23 1 1.322147 0.920720 0.565572 11.00000 0.02639 0.03425 = 0.03397 0.02036 0.01420 0.01737 F1 3 0.264800 0.174004 0.022737 11.00000 0.03317 0.08222 = 0.09748 0.06701 0.03425 0.02224 F2 3 0.486249 0.210876 0.116023 11.00000 0.04540 0.09426 = 0.06234 0.06298 0.00601 0.00979 F3 3 0.381571 0.054440 -0.083433 11.00000 0.11646 0.03812 = 0.07696 0.03006 0.05017 0.02432 F4 3 1.150902 0.819706 0.658460 11.00000 0.03545 0.04012 = 0.05124 0.02841 0.02684 0.02097 F5 3 1.175455 0.675252 0.478669 11.00000 0.03455 0.03344 = 0.03857 0.01197 0.00392 0.01299 F6 3 1.351270 0.776355 0.659015 11.00000 0.02956 0.04324 = 0.04477 0.02907 0.00624 0.01667 N1 4 0.821228 0.744075 0.306219 11.00000 0.02160 0.02330 = 0.02942 0.01731 0.01645 0.01206 AFIX 3 H1 2 0.811309 0.820907 0.321979 11.00000 -1.20000 AFIX 0 N2 4 1.186740 0.703048 0.178911 11.00000 0.01904 0.02549 = 0.02600 0.01236 0.01337 0.01030 AFIX 3 H2 2 1.268533 0.699617 0.156713 11.00000 -1.20000 AFIX 0 O1 5 0.427669 0.401335 0.014363 11.00000 0.06570 0.04091 = 0.06386 0.03032 0.05008 0.03083 O2 5 0.553984 0.278602 -0.096043 11.00000 0.03672 0.05234 = 0.05183 0.03526 0.03119 0.02943 O3 5 1.422753 0.900857 0.510216 11.00000 0.04729 0.05415 = 0.06396 0.04225 0.04049 0.03647 O4 5 1.278501 1.016864 0.595675 11.00000 0.05505 0.04315 = 0.08636 0.04365 0.05107 0.03571 H1A 2 0.500000 0.500000 0.000000 10.50000 0.11808 H3A 2 0.500000 1.000000 0.500000 10.50000 0.10820 HKLF 4 REM x2n1_angelo in P -1 REM R1 = 0.0493 for 5887 Fo > 4sig(Fo) and 0.0688 for all 7672 data REM 318 parameters refined using 0 restraints END WGHT 0.0679 0.2464 REM Highest difference peak 0.419, deepest hole -0.321, 1-sigma level 0.059 Q1 1 0.8757 0.4036 0.1515 11.00000 0.05 0.42 Q2 1 0.6201 0.5537 0.4867 11.00000 0.05 0.42 Q3 1 0.7448 0.6000 0.4657 11.00000 0.05 0.41 Q4 1 0.4422 0.0939 -0.0167 11.00000 0.05 0.40 Q5 1 1.2766 0.8533 0.5714 11.00000 0.05 0.39 Q6 1 0.9949 0.7892 0.2666 11.00000 0.05 0.39 Q7 1 0.4415 0.2677 0.1457 11.00000 0.05 0.39 Q8 1 1.0210 0.5857 0.1886 11.00000 0.05 0.38 Q9 1 0.4281 0.2405 -0.0139 11.00000 0.05 0.37 Q10 1 0.5414 0.6066 0.3641 11.00000 0.05 0.37 ; #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.017 0.01 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.93405(11) 0.72133(11) 0.25594(10) 0.01823(19) Uani 1 1 d . . . C2 C 0.95473(12) 0.58816(11) 0.20761(10) 0.01933(19) Uani 1 1 d . . . C3 C 1.08715(12) 0.58436(12) 0.17234(10) 0.0203(2) Uani 1 1 d . . . C4 C 1.16196(12) 0.82348(12) 0.21175(11) 0.0213(2) Uani 1 1 d . . . C5 C 1.03439(11) 0.83480(11) 0.24727(10) 0.01967(19) Uani 1 1 d . . . C6 C 1.28058(13) 0.94175(13) 0.20962(13) 0.0278(2) Uani 1 1 d . . . H6A H 1.2735 0.9189 0.1196 0.033 Uiso 1 1 calc R . . H6B H 1.3783 0.9492 0.2489 0.033 Uiso 1 1 calc R . . C7 C 1.26640(13) 1.08413(12) 0.28258(13) 0.0281(2) Uani 1 1 d . . . H7A H 1.2978 1.1194 0.3760 0.034 Uiso 1 1 calc R . . H7B H 1.3303 1.1530 0.2638 0.034 Uiso 1 1 calc R . . C8 C 1.10466(14) 1.06522(13) 0.23998(12) 0.0267(2) Uani 1 1 d . . . H8A H 1.0713 1.0234 0.1457 0.032 Uiso 1 1 calc R . . H8B H 1.0965 1.1573 0.2791 0.032 Uiso 1 1 calc R . . C9 C 1.00591(13) 0.96897(12) 0.28195(11) 0.0230(2) Uani 1 1 d . . . H9A H 1.0234 1.0212 0.3758 0.028 Uiso 1 1 calc R . . H9B H 0.9018 0.9436 0.2405 0.028 Uiso 1 1 calc R . . C10 C 1.11923(13) 0.46039(13) 0.12913(11) 0.0249(2) Uani 1 1 d . . . H10 H 1.2080 0.4605 0.1082 0.030 Uiso 1 1 calc R . . C11 C 1.01801(15) 0.33969(13) 0.11841(12) 0.0294(2) Uani 1 1 d . . . H11 H 1.0398 0.2585 0.0932 0.035 Uiso 1 1 calc R . . C12 C 0.88124(14) 0.33801(13) 0.14527(12) 0.0278(2) Uani 1 1 d . . . H12 H 0.8112 0.2543 0.1336 0.033 Uiso 1 1 calc R . . C13 C 0.85016(13) 0.45888(12) 0.18853(11) 0.0233(2) Uani 1 1 d . . . H13 H 0.7591 0.4558 0.2056 0.028 Uiso 1 1 calc R . . C14 C 0.73096(11) 0.67036(11) 0.35998(10) 0.01901(19) Uani 1 1 d . . . C15 C 0.79233(11) 0.63225(12) 0.44475(11) 0.0207(2) Uani 1 1 d . . . H15 H 0.8943 0.6514 0.4654 0.025 Uiso 1 1 calc R . . C16 C 0.70175(11) 0.56543(11) 0.49890(11) 0.01926(19) Uani 1 1 d . . . H16 H 0.7442 0.5396 0.5551 0.023 Uiso 1 1 calc R . . C17 C 0.54809(11) 0.53590(11) 0.47095(10) 0.01712(18) Uani 1 1 d . . . C18 C 0.49064(12) 0.57968(14) 0.38846(12) 0.0267(2) Uani 1 1 d . . . H18 H 0.3895 0.5639 0.3699 0.032 Uiso 1 1 calc R . . C19 C 0.57998(12) 0.64604(14) 0.33329(12) 0.0258(2) Uani 1 1 d . . . H19 H 0.5387 0.6741 0.2786 0.031 Uiso 1 1 calc R . . C20 C 0.46775(13) 0.29728(14) -0.03080(12) 0.0262(2) Uani 1 1 d . . . C21 C 0.39813(15) 0.18297(16) 0.00625(14) 0.0331(3) Uani 1 1 d . . . C22 C 0.24954(13) 0.79766(13) 0.59216(12) 0.0265(2) Uani 1 1 d . . . C23 C 0.32215(14) 0.92072(14) 0.56557(13) 0.0281(2) Uani 1 1 d . . . F1 F 0.26480(11) 0.17400(14) 0.02274(13) 0.0602(3) Uani 1 1 d . . . F2 F 0.48625(12) 0.21088(14) 0.11602(11) 0.0629(3) Uani 1 1 d . . . F3 F 0.38157(18) 0.05444(12) -0.08343(13) 0.0755(4) Uani 1 1 d . . . F4 F 0.15090(9) 0.81971(9) 0.65846(9) 0.03674(19) Uani 1 1 d . . . F5 F 0.17546(9) 0.67525(9) 0.47867(8) 0.0385(2) Uani 1 1 d . . . F6 F 0.35127(9) 0.77636(9) 0.65902(8) 0.03601(19) Uani 1 1 d . . . N1 N 0.82123(10) 0.74407(10) 0.30622(10) 0.02121(18) Uani 1 1 d . . . H1 H 0.8113 0.8209 0.3220 0.025 Uiso 1 1 d R . . N2 N 1.18674(10) 0.70305(10) 0.17891(9) 0.02245(19) Uani 1 1 d . . . H2 H 1.2685 0.6996 0.1567 0.027 Uiso 1 1 d R . . O1 O 0.42767(15) 0.40133(12) 0.01436(13) 0.0491(3) Uani 1 1 d . . . O2 O 0.55398(11) 0.27860(12) -0.09604(11) 0.0380(2) Uani 1 1 d . . . O3 O 0.42275(13) 0.90086(12) 0.51022(12) 0.0430(3) Uani 1 1 d . . . O4 O 0.27850(14) 1.01686(12) 0.59567(14) 0.0493(3) Uani 1 1 d . . . H1A H 0.5000 0.5000 0.0000 0.118(15) Uiso 1 2 d S . . H3A H 0.5000 1.0000 0.5000 0.108(14) Uiso 1 2 d S . . 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 0.0172(4) 0.0213(5) 0.0183(4) 0.0102(4) 0.0090(3) 0.0079(4) C2 0.0202(4) 0.0210(5) 0.0186(4) 0.0098(4) 0.0098(4) 0.0085(4) C3 0.0202(4) 0.0236(5) 0.0198(5) 0.0109(4) 0.0097(4) 0.0098(4) C4 0.0199(4) 0.0226(5) 0.0213(5) 0.0097(4) 0.0112(4) 0.0074(4) C5 0.0192(4) 0.0202(5) 0.0205(5) 0.0099(4) 0.0108(4) 0.0069(4) C6 0.0239(5) 0.0238(5) 0.0325(6) 0.0107(5) 0.0178(4) 0.0057(4) C7 0.0267(5) 0.0216(5) 0.0327(6) 0.0114(5) 0.0162(5) 0.0050(4) C8 0.0295(5) 0.0229(5) 0.0304(6) 0.0144(5) 0.0155(5) 0.0085(4) C9 0.0234(5) 0.0220(5) 0.0278(5) 0.0133(4) 0.0142(4) 0.0096(4) C10 0.0263(5) 0.0287(6) 0.0243(5) 0.0123(4) 0.0122(4) 0.0160(4) C11 0.0379(6) 0.0260(6) 0.0299(6) 0.0135(5) 0.0151(5) 0.0181(5) C12 0.0344(6) 0.0226(5) 0.0288(6) 0.0130(4) 0.0149(5) 0.0111(5) C13 0.0245(5) 0.0207(5) 0.0241(5) 0.0097(4) 0.0118(4) 0.0078(4) C14 0.0184(4) 0.0206(4) 0.0231(5) 0.0123(4) 0.0128(4) 0.0089(4) C15 0.0147(4) 0.0240(5) 0.0272(5) 0.0145(4) 0.0096(4) 0.0078(4) C16 0.0158(4) 0.0223(5) 0.0249(5) 0.0145(4) 0.0084(4) 0.0086(4) C17 0.0155(4) 0.0185(4) 0.0203(4) 0.0103(4) 0.0090(3) 0.0074(3) C18 0.0166(4) 0.0420(7) 0.0353(6) 0.0280(5) 0.0121(4) 0.0131(4) C19 0.0198(5) 0.0397(6) 0.0327(6) 0.0270(5) 0.0131(4) 0.0140(4) C20 0.0236(5) 0.0345(6) 0.0250(5) 0.0166(5) 0.0111(4) 0.0124(4) C21 0.0291(6) 0.0414(7) 0.0365(7) 0.0245(6) 0.0135(5) 0.0134(5) C22 0.0230(5) 0.0297(6) 0.0326(6) 0.0166(5) 0.0096(4) 0.0150(4) C23 0.0264(5) 0.0342(6) 0.0340(6) 0.0204(5) 0.0142(5) 0.0174(5) F1 0.0332(5) 0.0822(8) 0.0975(9) 0.0670(7) 0.0343(5) 0.0222(5) F2 0.0454(5) 0.0943(9) 0.0623(7) 0.0630(7) 0.0060(5) 0.0098(5) F3 0.1165(11) 0.0381(6) 0.0770(8) 0.0301(6) 0.0502(8) 0.0243(6) F4 0.0355(4) 0.0401(4) 0.0512(5) 0.0284(4) 0.0268(4) 0.0210(4) F5 0.0345(4) 0.0334(4) 0.0386(4) 0.0120(3) 0.0039(3) 0.0130(3) F6 0.0296(4) 0.0432(5) 0.0448(5) 0.0291(4) 0.0062(3) 0.0167(3) N1 0.0216(4) 0.0233(4) 0.0294(5) 0.0173(4) 0.0164(4) 0.0121(3) N2 0.0190(4) 0.0255(5) 0.0260(4) 0.0124(4) 0.0134(3) 0.0103(3) O1 0.0657(7) 0.0409(6) 0.0639(7) 0.0303(6) 0.0501(6) 0.0308(6) O2 0.0367(5) 0.0523(6) 0.0518(6) 0.0353(5) 0.0312(5) 0.0294(5) O3 0.0473(6) 0.0541(7) 0.0640(7) 0.0423(6) 0.0405(6) 0.0365(5) O4 0.0550(7) 0.0432(6) 0.0864(9) 0.0437(6) 0.0511(7) 0.0357(5) #----------------------------------------------------------------------------# # 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_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C21 1.321(2) . . yes F2 C21 1.319(2) . . yes F3 C21 1.322(2) . . yes F4 C22 1.3285(16) . . yes F5 C22 1.3468(17) . . yes F6 C22 1.3318(17) . . yes O1 C20 1.262(2) . . yes O2 C20 1.2138(18) . . yes O1 H1A 1.2200 . . no O3 C23 1.267(2) . . yes O4 C23 1.206(2) . . yes O3 H3A 1.2200 . . no N1 C14 1.4269(17) . . yes N1 C1 1.3523(15) . . yes N2 C4 1.3455(18) . . yes N2 C3 1.3680(18) . . yes N1 H1 0.8400 . . no N2 H2 0.8800 . . no C1 C5 1.4177(18) . . no C1 C2 1.4440(18) . . no C2 C13 1.4165(19) . . no C2 C3 1.4130(17) . . no C3 C10 1.410(2) . . no C4 C5 1.3850(17) . . no C4 C6 1.501(2) . . no C5 C9 1.5063(19) . . no C6 C7 1.518(2) . . no C7 C8 1.517(2) . . no C8 C9 1.524(2) . . no C10 C11 1.370(2) . . no C11 C12 1.407(2) . . no C12 C13 1.373(2) . . no C14 C15 1.3844(18) . . no C14 C19 1.3860(18) . . no C15 C16 1.3878(18) . . no C16 C17 1.3998(16) . . no C17 C17 1.4840(17) . 2_666 no C17 C18 1.395(2) . . no C18 C19 1.388(2) . . no C6 H6B 0.9700 . . no C6 H6A 0.9700 . . no C7 H7B 0.9700 . . no C7 H7A 0.9700 . . no C8 H8B 0.9700 . . no C8 H8A 0.9700 . . no C9 H9B 0.9700 . . no C9 H9A 0.9700 . . no C10 H10 0.9300 . . no C11 H11 0.9300 . . no C12 H12 0.9300 . . no C13 H13 0.9300 . . no C15 H15 0.9300 . . no C16 H16 0.9300 . . no C18 H18 0.9300 . . no C19 H19 0.9300 . . no C20 C21 1.536(2) . . no C22 C23 1.542(2) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C20 O1 H1A 113.00 . . . no C23 O3 H3A 116.00 . . . no C1 N1 C14 129.63(12) . . . yes C3 N2 C4 123.05(11) . . . yes C1 N1 H1 117.00 . . . no C14 N1 H1 112.00 . . . no C4 N2 H2 118.00 . . . no C3 N2 H2 119.00 . . . no N1 C1 C5 117.27(11) . . . yes N1 C1 C2 123.90(12) . . . yes C2 C1 C5 118.80(10) . . . no C3 C2 C13 117.03(12) . . . no C1 C2 C13 125.10(11) . . . no C1 C2 C3 117.84(12) . . . no N2 C3 C2 119.63(12) . . . yes C2 C3 C10 121.62(13) . . . no N2 C3 C10 118.75(11) . . . yes N2 C4 C6 116.09(11) . . . yes N2 C4 C5 120.43(12) . . . yes C5 C4 C6 123.47(12) . . . no C1 C5 C4 119.46(12) . . . no C4 C5 C9 120.26(12) . . . no C1 C5 C9 120.23(11) . . . no C4 C6 C7 112.30(12) . . . no C6 C7 C8 109.17(12) . . . no C7 C8 C9 110.05(12) . . . no C5 C9 C8 112.89(11) . . . no C3 C10 C11 119.18(13) . . . no C10 C11 C12 120.34(14) . . . no C11 C12 C13 120.59(14) . . . no C2 C13 C12 121.04(13) . . . no C15 C14 C19 119.67(12) . . . no N1 C14 C19 118.47(12) . . . yes N1 C14 C15 121.70(11) . . . yes C14 C15 C16 120.01(11) . . . no C15 C16 C17 121.63(11) . . . no C16 C17 C18 116.93(12) . . . no C16 C17 C17 121.31(11) . . 2_666 no C17 C17 C18 121.75(11) 2_666 . . no C17 C18 C19 121.97(12) . . . no C14 C19 C18 119.75(13) . . . no C4 C6 H6B 109.00 . . . no C7 C6 H6B 109.00 . . . no H6A C6 H6B 108.00 . . . no C7 C6 H6A 109.00 . . . no C4 C6 H6A 109.00 . . . no C6 C7 H7A 110.00 . . . no C8 C7 H7B 110.00 . . . no C6 C7 H7B 110.00 . . . no H7A C7 H7B 108.00 . . . no C8 C7 H7A 110.00 . . . no C9 C8 H8A 110.00 . . . no C9 C8 H8B 110.00 . . . no C7 C8 H8B 110.00 . . . no H8A C8 H8B 108.00 . . . no C7 C8 H8A 110.00 . . . no C5 C9 H9B 109.00 . . . no C8 C9 H9B 109.00 . . . no H9A C9 H9B 108.00 . . . no C5 C9 H9A 109.00 . . . no C8 C9 H9A 109.00 . . . no C3 C10 H10 120.00 . . . no C11 C10 H10 120.00 . . . no C10 C11 H11 120.00 . . . no C12 C11 H11 120.00 . . . no C13 C12 H12 120.00 . . . no C11 C12 H12 120.00 . . . no C12 C13 H13 119.00 . . . no C2 C13 H13 119.00 . . . no C14 C15 H15 120.00 . . . no C16 C15 H15 120.00 . . . no C17 C16 H16 119.00 . . . no C15 C16 H16 119.00 . . . no C19 C18 H18 119.00 . . . no C17 C18 H18 119.00 . . . no C14 C19 H19 120.00 . . . no C18 C19 H19 120.00 . . . no O1 C20 O2 128.61(17) . . . yes O2 C20 C21 117.65(14) . . . yes O1 C20 C21 113.73(13) . . . yes F1 C21 C20 113.45(15) . . . yes F1 C21 F2 107.82(13) . . . yes F2 C21 C20 109.79(14) . . . yes F3 C21 C20 112.12(13) . . . yes F2 C21 F3 106.84(16) . . . yes F1 C21 F3 106.50(16) . . . yes F4 C22 F5 106.78(12) . . . yes F4 C22 F6 107.72(11) . . . yes F5 C22 F6 107.34(13) . . . yes F5 C22 C23 110.33(11) . . . yes F6 C22 C23 111.76(12) . . . yes F4 C22 C23 112.64(13) . . . yes O3 C23 C22 110.94(14) . . . yes O4 C23 C22 119.64(14) . . . yes O3 C23 O4 129.42(17) . . . yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N1 C1 C2 21.30(18) . . . . no C14 N1 C1 C5 -160.59(11) . . . . no C1 N1 C14 C15 43.60(18) . . . . no C1 N1 C14 C19 -141.06(13) . . . . no C3 N2 C4 C6 -177.94(11) . . . . no C4 N2 C3 C10 176.10(11) . . . . no C4 N2 C3 C2 -3.35(17) . . . . no C3 N2 C4 C5 3.21(17) . . . . no C2 C1 C5 C4 -9.71(15) . . . . no N1 C1 C2 C13 9.70(17) . . . . no C5 C1 C2 C3 9.40(15) . . . . no N1 C1 C5 C9 -5.35(15) . . . . no N1 C1 C5 C4 172.08(10) . . . . no N1 C1 C2 C3 -172.52(10) . . . . no C2 C1 C5 C9 172.86(10) . . . . no C5 C1 C2 C13 -168.39(11) . . . . no C1 C2 C3 C10 177.50(10) . . . . no C13 C2 C3 N2 174.90(10) . . . . no C1 C2 C3 N2 -3.07(16) . . . . no C1 C2 C13 C12 -178.31(11) . . . . no C13 C2 C3 C10 -4.53(16) . . . . no C3 C2 C13 C12 3.89(17) . . . . no N2 C3 C10 C11 -178.04(11) . . . . no C2 C3 C10 C11 1.40(18) . . . . no C6 C4 C5 C1 -175.26(11) . . . . no C6 C4 C5 C9 2.17(17) . . . . no N2 C4 C5 C9 -179.06(10) . . . . no C5 C4 C6 C7 14.74(17) . . . . no N2 C4 C6 C7 -164.08(11) . . . . no N2 C4 C5 C1 3.51(16) . . . . no C1 C5 C9 C8 -167.77(10) . . . . no C4 C5 C9 C8 14.83(15) . . . . no C4 C6 C7 C8 -47.48(15) . . . . no C6 C7 C8 C9 65.36(14) . . . . no C7 C8 C9 C5 -48.21(14) . . . . no C3 C10 C11 C12 2.51(19) . . . . no C10 C11 C12 C13 -3.2(2) . . . . no C11 C12 C13 C2 -0.16(18) . . . . no N1 C14 C15 C16 177.59(11) . . . . no C19 C14 C15 C16 2.31(19) . . . . no N1 C14 C19 C18 -177.45(12) . . . . no C15 C14 C19 C18 -2.0(2) . . . . no C14 C15 C16 C17 -0.58(19) . . . . no C15 C16 C17 C18 -1.38(18) . . . . no C15 C16 C17 C17 179.86(11) . . . 2_666 no C16 C17 C18 C19 1.7(2) . . . . no C17 C17 C18 C19 -179.57(12) 2_666 . . . no C16 C17 C17 C16 179.98(13) . . 2_666 2_666 no C16 C17 C17 C18 -1.30(18) . . 2_666 2_666 no C18 C17 C17 C16 1.30(18) . . 2_666 2_666 no C18 C17 C17 C18 179.98(15) . . 2_666 2_666 no C17 C18 C19 C14 -0.0(2) . . . . no O1 C20 C21 F1 29.76(18) . . . . no O1 C20 C21 F2 -90.94(16) . . . . no O1 C20 C21 F3 150.47(15) . . . . no O2 C20 C21 F1 -151.45(14) . . . . no O2 C20 C21 F2 87.84(16) . . . . no O2 C20 C21 F3 -30.75(19) . . . . no F4 C22 C23 O3 175.52(12) . . . . no F4 C22 C23 O4 -5.59(19) . . . . no F5 C22 C23 O3 -65.26(15) . . . . no F5 C22 C23 O4 113.63(15) . . . . no F6 C22 C23 O3 54.08(16) . . . . no F6 C22 C23 O4 -127.03(15) . . . . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N1 H1 O4 0.8400 2.1600 2.9425(19) 155.00 2_676 yes O1 H1A O1 1.2200 1.2200 2.448(2) 180.00 2_665 yes N2 H2 O2 0.8800 1.9500 2.8098(16) 168.00 2_765 yes O3 H3A O3 1.2200 1.2200 2.431(2) 180.00 2_676 yes C19 H19 O2 0.9300 2.5600 3.4747(19) 169.00 2_665 yes _database_code_depnum_ccdc_archive 'CCDC 945410'