# Electronic Supplementary Material (ESI) for Nanoscale # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_HS006_Fluorescence _database_code_depnum_ccdc_archive 'CCDC 837539' #TrackingRef 'web_deposit_cif_file_0_ToshimasaKatagiri_ #1312169855.Fluorescence.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C21.50 H16.50 F6 O6' _chemical_formula_moiety 'C18 H14 F6 O6, 0.25(C14 H10)' _chemical_formula_weight 484.85 _chemical_melting_point ? _chemical_absolute_configuration rmad #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 13.1176(10) _cell_length_b 5.17328(11) _cell_length_c 17.1353(12) _cell_angle_alpha 90.0000 _cell_angle_beta 112.756(8) _cell_angle_gamma 90.0000 _cell_volume 1072.30(13) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9211 _cell_measurement_theta_min 3.65 _cell_measurement_theta_max 68.21 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 5.100 _exptl_crystal_size_mid 0.015 _exptl_crystal_size_min 0.015 _exptl_crystal_density_diffrn 1.502 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 495.00 _exptl_absorpt_coefficient_mu 1.262 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.691 _exptl_absorpt_correction_T_max 0.881 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 298 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 12752 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_theta_max 68.21 _diffrn_reflns_theta_full 68.21 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measured_fraction_theta_full 0.985 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3574 _reflns_number_gt 3358 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1669 _refine_ls_number_restraints 280 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3574 _refine_ls_number_parameters 293 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1160P)^2^+0.2036P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.770 _refine_diff_density_min -0.490 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1405 Friedel Pairs' _refine_ls_abs_structure_Flack 0.1(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.0727 0.0534 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 F1 F 1.28376(18) 1.2761(6) 0.18890(13) 0.0537(6) Uani 1.0 2 d . . . F2 F 1.34894(17) 0.9558(6) 0.14255(15) 0.0591(7) Uani 1.0 2 d . . . F3 F 1.34255(19) 1.3337(6) 0.08953(14) 0.0633(8) Uani 1.0 2 d . . . F4 F 0.71174(15) 0.5620(5) 0.22369(12) 0.0419(5) Uani 1.0 2 d . . . F5 F 0.62227(16) 0.9104(5) 0.22738(12) 0.0459(6) Uani 1.0 2 d . . . O1 O 1.10866(17) 0.9378(5) 0.14980(13) 0.0317(5) Uani 1.0 2 d . . . O2 O 1.09004(17) 0.6923(5) 0.03597(14) 0.0343(5) Uani 1.0 2 d . . . O3 O 1.17982(18) 1.0773(5) -0.02665(13) 0.0333(5) Uani 1.0 2 d . . . O4 O 0.80876(16) 0.9428(5) 0.16783(12) 0.0291(5) Uani 1.0 2 d . . . O5 O 0.69623(16) 1.1888(5) 0.06164(13) 0.0311(5) Uani 1.0 2 d . . . O6 O 0.52429(16) 0.8912(5) 0.04164(13) 0.0312(5) Uani 1.0 2 d . . . C1 C 1.1414(3) 0.7658(8) 0.3432(2) 0.0393(8) Uani 1.0 2 d . . . C2 C 1.0644(3) 0.8448(7) 0.2676(2) 0.0328(7) Uani 1.0 2 d . . . C3 C 0.9905(3) 1.0494(7) 0.26638(19) 0.0326(7) Uani 1.0 2 d . . . C4 C 1.0006(3) 1.1708(8) 0.34035(19) 0.0364(8) Uani 1.0 2 d . . . C5 C 1.0828(3) 1.0944(8) 0.41910(19) 0.0391(8) Uani 1.0 2 d . . . C6 C 1.0966(4) 1.2221(10) 0.4957(3) 0.0511(10) Uani 1.0 2 d . . . C7 C 1.1749(4) 1.1422(10) 0.5701(3) 0.0570(11) Uani 1.0 2 d . . . C8 C 1.2417(4) 0.9300(11) 0.5724(3) 0.0587(11) Uani 1.0 2 d . . . C9 C 1.2321(4) 0.8042(10) 0.5002(3) 0.0554(10) Uani 1.0 2 d . . . C10 C 1.1528(3) 0.8850(9) 0.4207(2) 0.0412(8) Uani 1.0 2 d . . . C11 C 1.0620(3) 0.7337(7) 0.18602(19) 0.0322(7) Uani 1.0 2 d . . . C12 C 1.1190(3) 0.8885(7) 0.07722(18) 0.0288(7) Uani 1.0 2 d . . . C13 C 1.1732(3) 1.1146(7) 0.05146(18) 0.0292(7) Uani 1.0 2 d . . . C14 C 1.2880(3) 1.1704(8) 0.1194(2) 0.0402(8) Uani 1.0 2 d . . . C15 C 0.8978(3) 1.1336(7) 0.18500(19) 0.0309(7) Uani 1.0 2 d . . . C16 C 0.7135(3) 0.9984(6) 0.10550(17) 0.0259(6) Uani 1.0 2 d . . . C17 C 0.6270(3) 0.7916(7) 0.09462(18) 0.0283(7) Uani 1.0 2 d . . . C18 C 0.6238(3) 0.7071(8) 0.17903(19) 0.0339(7) Uani 1.0 2 d . . . F6 F 0.53387(16) 0.5682(5) 0.16645(12) 0.0487(6) Uani 1.0 2 d . . . H3A H 1.1982 0.9276 -0.0302 0.0399 Uiso 1.0 2 calc R . . H6A H 0.4842 0.7727 0.0154 0.0374 Uiso 1.0 2 calc R . . H1 H 1.1880 0.6294 0.3440 0.0472 Uiso 1.0 2 calc R . . H4 H 0.9527 1.3051 0.3388 0.0437 Uiso 1.0 2 calc R . . H6 H 1.0515 1.3618 0.4949 0.0613 Uiso 1.0 2 calc R . . H7 H 1.1842 1.2293 0.6199 0.0683 Uiso 1.0 2 calc R . . H8 H 1.2935 0.8738 0.6241 0.0704 Uiso 1.0 2 calc R . . H9 H 1.2778 0.6642 0.5029 0.0665 Uiso 1.0 2 calc R . . H11A H 1.1063 0.5777 0.1963 0.0386 Uiso 1.0 2 calc R . . H11B H 0.9869 0.6929 0.1482 0.0386 Uiso 1.0 2 calc R . . H13 H 1.1273 1.2676 0.0469 0.0350 Uiso 1.0 2 calc R . . H15A H 0.8719 1.3047 0.1914 0.0371 Uiso 1.0 2 calc R . . H15B H 0.9233 1.1376 0.1389 0.0371 Uiso 1.0 2 calc R . . H17 H 0.6440 0.6409 0.0671 0.0340 Uiso 1.0 2 calc R . . C19 C 0.442(5) 0.746(9) 0.360(4) 0.2521 Uiso 0.2500 2 d . . . H19 H 0.4048 0.7489 0.3018 0.3026 Uiso 0.2500 2 calc R . . C20 C 0.475(6) 0.972(8) 0.404(5) 0.2721 Uiso 0.2500 2 d . . . H20 H 0.4606 1.1285 0.3748 0.3266 Uiso 0.2500 2 calc R . . C21 C 0.533(6) 0.971(9) 0.494(5) 0.3011 Uiso 0.2500 2 d . . . H21 H 0.5546 1.1259 0.5229 0.3614 Uiso 0.2500 2 calc R . . C22 C 0.556(4) 0.742(11) 0.538(4) 0.3091 Uiso 0.2500 2 d . . . H22 H 0.5927 0.7436 0.5961 0.3709 Uiso 0.2500 2 calc R . . C23 C 0.522(2) 0.500(9) 0.494(2) 0.2967 Uiso 0.2500 2 d . . . C24 C 0.546(2) 0.264(11) 0.5373(10) 0.2979 Uiso 0.2500 2 d . . . H24 H 0.5831 0.2631 0.5958 0.3575 Uiso 0.2500 2 calc R . . C25 C 0.513(3) 0.030(9) 0.4935(17) 0.2881 Uiso 0.2500 2 d . . . C26 C 0.537(5) -0.214(11) 0.537(4) 0.2940 Uiso 0.2500 2 d . . . H26 H 0.5754 -0.2175 0.5959 0.3528 Uiso 0.2500 2 calc R . . C27 C 0.505(7) -0.441(9) 0.494(5) 0.2824 Uiso 0.2500 2 d . . . H27 H 0.5210 -0.5974 0.5227 0.3389 Uiso 0.2500 2 calc R . . C28 C 0.447(6) -0.439(8) 0.404(5) 0.2509 Uiso 0.2500 2 d . . . H28 H 0.4252 -0.5945 0.3747 0.3011 Uiso 0.2500 2 calc R . . C29 C 0.422(4) -0.211(9) 0.360(4) 0.2466 Uiso 0.2500 2 d . . . H29 H 0.3839 -0.2118 0.3018 0.2960 Uiso 0.2500 2 calc R . . C30 C 0.455(3) 0.031(8) 0.4043(17) 0.2521 Uiso 0.2500 2 d . . . C31 C 0.4318(13) 0.267(9) 0.3606(10) 0.2494 Uiso 0.2500 2 d . . . H31 H 0.3939 0.2686 0.3022 0.2993 Uiso 0.2500 2 calc R . . C32 C 0.465(3) 0.502(8) 0.404(2) 0.2596 Uiso 0.2500 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.0567(13) 0.0670(16) 0.0388(11) -0.0250(12) 0.0199(9) -0.0187(11) F2 0.0323(10) 0.0778(18) 0.0592(14) 0.0078(12) 0.0089(9) 0.0033(13) F3 0.0579(14) 0.083(2) 0.0504(13) -0.0402(14) 0.0230(11) -0.0053(12) F4 0.0375(10) 0.0461(12) 0.0361(10) -0.0024(9) 0.0076(8) 0.0121(9) F5 0.0461(11) 0.0592(14) 0.0374(10) -0.0050(10) 0.0215(9) -0.0081(10) O1 0.0328(11) 0.0336(13) 0.0327(10) -0.0060(9) 0.0173(9) -0.0019(10) O2 0.0369(11) 0.0285(12) 0.0399(12) -0.0009(10) 0.0178(9) -0.0045(9) O3 0.0387(12) 0.0306(12) 0.0334(10) 0.0038(10) 0.0171(9) 0.0003(10) O4 0.0245(10) 0.0315(12) 0.0294(10) -0.0013(9) 0.0084(8) 0.0012(9) O5 0.0292(11) 0.0304(12) 0.0329(11) -0.0003(9) 0.0110(9) 0.0026(9) O6 0.0239(10) 0.0295(12) 0.0333(11) -0.0005(9) 0.0036(8) 0.0010(10) C1 0.0339(16) 0.044(2) 0.0407(16) 0.0005(15) 0.0151(13) 0.0051(15) C2 0.0285(14) 0.0371(18) 0.0338(15) -0.0047(12) 0.0131(12) 0.0040(13) C3 0.0268(13) 0.0408(18) 0.0314(15) -0.0080(13) 0.0126(11) 0.0019(13) C4 0.0306(15) 0.0443(19) 0.0332(16) -0.0042(14) 0.0111(13) -0.0029(14) C5 0.0396(16) 0.049(2) 0.0285(14) -0.0081(15) 0.0124(13) 0.0010(14) C6 0.055(2) 0.062(3) 0.0366(17) -0.0071(19) 0.0171(15) -0.0042(18) C7 0.062(3) 0.074(3) 0.0298(17) -0.011(2) 0.0122(16) -0.0055(18) C8 0.054(3) 0.083(3) 0.0291(16) -0.004(3) 0.0061(15) 0.0070(19) C9 0.050(2) 0.064(3) 0.0432(19) 0.001(2) 0.0075(16) 0.0100(18) C10 0.0372(16) 0.050(2) 0.0339(16) -0.0071(15) 0.0114(13) 0.0056(15) C11 0.0311(15) 0.0294(17) 0.0369(15) -0.0003(13) 0.0142(12) 0.0028(13) C12 0.0240(13) 0.0281(16) 0.0330(14) 0.0032(12) 0.0095(11) 0.0008(12) C13 0.0316(14) 0.0265(16) 0.0317(14) 0.0023(12) 0.0147(12) -0.0003(12) C14 0.0386(16) 0.049(2) 0.0366(16) -0.0117(15) 0.0184(13) -0.0007(15) C15 0.0257(14) 0.0348(19) 0.0310(15) -0.0029(12) 0.0098(12) 0.0002(13) C16 0.0239(13) 0.0303(16) 0.0246(13) 0.0022(11) 0.0108(11) -0.0011(12) C17 0.0282(14) 0.0271(16) 0.0271(13) 0.0008(12) 0.0079(11) 0.0004(12) C18 0.0271(14) 0.0420(19) 0.0308(14) -0.0031(13) 0.0091(11) 0.0021(13) F6 0.0373(10) 0.0632(15) 0.0416(11) -0.0170(10) 0.0110(8) 0.0104(11) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'Il Milione (Burla, et al., 2007)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C14 1.331(5) yes . . F2 C14 1.336(5) yes . . F3 C14 1.330(6) yes . . F4 C18 1.341(4) yes . . F5 C18 1.344(5) yes . . O1 C11 1.473(5) yes . . O1 C12 1.327(5) yes . . O2 C12 1.211(4) yes . . O3 C13 1.388(5) yes . . O4 C15 1.470(4) yes . . O4 C16 1.324(3) yes . . O5 C16 1.206(4) yes . . O6 C17 1.400(4) yes . . C1 C2 1.361(4) yes . . C1 C10 1.420(6) yes . . C2 C3 1.429(5) yes . . C2 C11 1.501(5) yes . . C3 C4 1.374(5) yes . . C3 C15 1.517(4) yes . . C4 C5 1.419(4) yes . . C5 C6 1.417(6) yes . . C5 C10 1.414(6) yes . . C6 C7 1.357(5) yes . . C7 C8 1.395(8) yes . . C8 C9 1.360(7) yes . . C9 C10 1.419(5) yes . . C12 C13 1.521(5) yes . . C13 C14 1.532(4) yes . . C16 C17 1.518(5) yes . . C17 C18 1.527(5) yes . . C18 F6 1.326(4) yes . . C19 C20 1.367 yes . . C19 C32 1.440 yes . . C20 C21 1.431 yes . . C21 C22 1.368 yes . . C22 C23 1.440 yes . . C23 C24 1.404 yes . . C24 C25 1.404 yes . . C25 C26 1.440 yes . . C25 C30 1.419 yes . . C26 C27 1.368 yes . . C27 C28 1.431 yes . . C28 C29 1.368 yes . . C29 C30 1.440 yes . . C30 C31 1.404 yes . . C31 C32 1.404 yes . . O3 H3A 0.820 no . . O6 H6A 0.820 no . . C1 H1 0.930 no . . C4 H4 0.930 no . . C6 H6 0.930 no . . C7 H7 0.930 no . . C8 H8 0.930 no . . C9 H9 0.930 no . . C11 H11A 0.970 no . . C11 H11B 0.970 no . . C13 H13 0.980 no . . C15 H15A 0.970 no . . C15 H15B 0.970 no . . C17 H17 0.980 no . . C19 H19 0.930 no . . C20 H20 0.930 no . . C21 H21 0.930 no . . C22 H22 0.930 no . . C24 H24 0.930 no . . C26 H26 0.930 no . . C27 H27 0.930 no . . C28 H28 0.930 no . . C29 H29 0.930 no . . C31 H31 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C11 O1 C12 117.9(3) yes . . . C15 O4 C16 116.4(3) yes . . . C2 C1 C10 122.1(4) yes . . . C1 C2 C3 119.1(4) yes . . . C1 C2 C11 120.8(4) yes . . . C3 C2 C11 120.0(3) yes . . . C2 C3 C4 120.1(3) yes . . . C2 C3 C15 121.6(3) yes . . . C4 C3 C15 118.3(3) yes . . . C3 C4 C5 121.1(4) yes . . . C4 C5 C6 121.9(4) yes . . . C4 C5 C10 118.8(4) yes . . . C6 C5 C10 119.3(3) yes . . . C5 C6 C7 120.5(5) yes . . . C6 C7 C8 120.4(4) yes . . . C7 C8 C9 121.0(4) yes . . . C8 C9 C10 120.5(5) yes . . . C1 C10 C5 118.8(3) yes . . . C1 C10 C9 122.9(4) yes . . . C5 C10 C9 118.3(4) yes . . . O1 C11 C2 104.8(3) yes . . . O1 C12 O2 125.8(4) yes . . . O1 C12 C13 110.7(3) yes . . . O2 C12 C13 123.5(3) yes . . . O3 C13 C12 112.6(3) yes . . . O3 C13 C14 110.5(3) yes . . . C12 C13 C14 110.9(3) yes . . . F1 C14 F2 107.6(3) yes . . . F1 C14 F3 107.3(4) yes . . . F1 C14 C13 112.9(4) yes . . . F2 C14 F3 107.0(4) yes . . . F2 C14 C13 111.6(3) yes . . . F3 C14 C13 110.2(3) yes . . . O4 C15 C3 106.5(3) yes . . . O4 C16 O5 124.9(3) yes . . . O4 C16 C17 111.9(3) yes . . . O5 C16 C17 123.2(3) yes . . . O6 C17 C16 107.9(3) yes . . . O6 C17 C18 110.3(3) yes . . . C16 C17 C18 112.2(3) yes . . . F4 C18 F5 107.5(3) yes . . . F4 C18 C17 111.6(3) yes . . . F4 C18 F6 107.7(3) yes . . . F5 C18 C17 111.9(3) yes . . . F5 C18 F6 107.5(3) yes . . . C17 C18 F6 110.5(3) yes . . . C20 C19 C32 120.372 yes . . . C19 C20 C21 120.517 yes . . . C20 C21 C22 120.520 yes . . . C21 C22 C23 120.364 yes . . . C22 C23 C24 121.201 yes . . . C22 C23 C32 119.116 yes . . . C24 C23 C32 119.683 yes . . . C23 C24 C25 120.627 yes . . . C24 C25 C26 121.195 yes . . . C24 C25 C30 119.688 yes . . . C26 C25 C30 119.118 yes . . . C25 C26 C27 120.363 yes . . . C26 C27 C28 120.521 yes . . . C27 C28 C29 120.510 yes . . . C28 C29 C30 120.375 yes . . . C25 C30 C29 119.113 yes . . . C25 C30 C31 119.692 yes . . . C29 C30 C31 121.195 yes . . . C30 C31 C32 120.616 yes . . . C19 C32 C23 119.111 yes . . . C19 C32 C31 121.197 yes . . . C23 C32 C31 119.692 yes . . . C13 O3 H3A 109.472 no . . . C17 O6 H6A 109.473 no . . . C2 C1 H1 118.964 no . . . C10 C1 H1 118.961 no . . . C3 C4 H4 119.456 no . . . C5 C4 H4 119.456 no . . . C5 C6 H6 119.751 no . . . C7 C6 H6 119.757 no . . . C6 C7 H7 119.822 no . . . C8 C7 H7 119.819 no . . . C7 C8 H8 119.509 no . . . C9 C8 H8 119.514 no . . . C8 C9 H9 119.756 no . . . C10 C9 H9 119.762 no . . . O1 C11 H11A 110.784 no . . . O1 C11 H11B 110.789 no . . . C2 C11 H11A 110.789 no . . . C2 C11 H11B 110.786 no . . . H11A C11 H11B 108.861 no . . . O3 C13 H13 107.558 no . . . C12 C13 H13 107.561 no . . . C14 C13 H13 107.562 no . . . O4 C15 H15A 110.428 no . . . O4 C15 H15B 110.433 no . . . C3 C15 H15A 110.432 no . . . C3 C15 H15B 110.431 no . . . H15A C15 H15B 108.633 no . . . O6 C17 H17 108.784 no . . . C16 C17 H17 108.786 no . . . C18 C17 H17 108.795 no . . . H19 C19 C20 119.814 no . . . H19 C19 C32 119.815 no . . . C19 C20 H20 119.745 no . . . H20 C20 C21 119.738 no . . . C20 C21 H21 119.744 no . . . H21 C21 C22 119.736 no . . . C21 C22 H22 119.819 no . . . H22 C22 C23 119.817 no . . . C23 C24 H24 119.687 no . . . H24 C24 C25 119.686 no . . . C25 C26 H26 119.816 no . . . H26 C26 C27 119.821 no . . . C26 C27 H27 119.736 no . . . H27 C27 C28 119.744 no . . . C27 C28 H28 119.741 no . . . H28 C28 C29 119.750 no . . . C28 C29 H29 119.811 no . . . H29 C29 C30 119.814 no . . . C30 C31 H31 119.691 no . . . H31 C31 C32 119.693 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C11 O1 C12 O2 2.6(4) no . . . . C11 O1 C12 C13 -177.36(19) no . . . . C12 O1 C11 C2 178.4(2) no . . . . C15 O4 C16 O5 1.6(5) no . . . . C15 O4 C16 C17 -178.8(3) no . . . . C16 O4 C15 C3 171.2(3) no . . . . C2 C1 C10 C5 -0.8(6) no . . . . C2 C1 C10 C9 179.6(4) no . . . . C10 C1 C2 C3 -1.8(6) no . . . . C10 C1 C2 C11 173.6(4) no . . . . C1 C2 C3 C4 2.6(6) no . . . . C1 C2 C3 C15 -175.7(3) no . . . . C1 C2 C11 O1 -104.6(4) no . . . . C3 C2 C11 O1 70.8(4) no . . . . C11 C2 C3 C4 -172.8(3) no . . . . C11 C2 C3 C15 8.8(5) no . . . . C2 C3 C4 C5 -0.8(6) no . . . . C2 C3 C15 O4 78.6(4) no . . . . C4 C3 C15 O4 -99.7(4) no . . . . C15 C3 C4 C5 177.5(3) no . . . . C3 C4 C5 C6 178.1(4) no . . . . C3 C4 C5 C10 -1.8(6) no . . . . C4 C5 C6 C7 179.1(4) no . . . . C4 C5 C10 C1 2.6(6) no . . . . C4 C5 C10 C9 -177.8(4) no . . . . C6 C5 C10 C1 -177.3(4) no . . . . C6 C5 C10 C9 2.4(6) no . . . . C10 C5 C6 C7 -1.0(7) no . . . . C5 C6 C7 C8 -1.2(8) no . . . . C6 C7 C8 C9 2.0(8) no . . . . C7 C8 C9 C10 -0.6(8) no . . . . C8 C9 C10 C1 178.1(4) no . . . . C8 C9 C10 C5 -1.5(7) no . . . . O1 C12 C13 O3 -176.5(2) no . . . . O1 C12 C13 C14 59.2(3) no . . . . O2 C12 C13 O3 3.6(4) no . . . . O2 C12 C13 C14 -120.8(3) no . . . . O3 C13 C14 F1 162.7(3) no . . . . O3 C13 C14 F2 -76.0(4) no . . . . O3 C13 C14 F3 42.7(4) no . . . . C12 C13 C14 F1 -71.8(4) no . . . . C12 C13 C14 F2 49.5(4) no . . . . C12 C13 C14 F3 168.3(3) no . . . . O4 C16 C17 O6 167.0(3) no . . . . O4 C16 C17 C18 45.3(4) no . . . . O5 C16 C17 O6 -13.4(5) no . . . . O5 C16 C17 C18 -135.1(3) no . . . . O6 C17 C18 F4 166.7(3) no . . . . O6 C17 C18 F5 -72.8(3) no . . . . O6 C17 C18 F6 46.9(4) no . . . . C16 C17 C18 F4 -73.0(4) no . . . . C16 C17 C18 F5 47.5(4) no . . . . C16 C17 C18 F6 167.2(3) no . . . . C20 C19 C32 C23 -0.1 no . . . . C20 C19 C32 C31 -179.9 no . . . . C32 C19 C20 C21 -0.2 no . . . . C19 C20 C21 C22 0.2 no . . . . C20 C21 C22 C23 0.1 no . . . . C21 C22 C23 C24 179.5 no . . . . C22 C23 C24 C25 -179.8 no . . . . C22 C23 C32 C31 -179.9 no . . . . C24 C23 C32 C19 -179.5 no . . . . C24 C23 C32 C31 0.3 no . . . . C32 C23 C24 C25 0.0 no . . . . C23 C24 C25 C26 179.5 no . . . . C23 C24 C25 C30 -0.4 no . . . . C24 C25 C26 C27 180.0 no . . . . C24 C25 C30 C29 -179.9 no . . . . C24 C25 C30 C31 0.4 no . . . . C26 C25 C30 C29 0.2 no . . . . C26 C25 C30 C31 -179.5 no . . . . C30 C25 C26 C27 -0.1 no . . . . C25 C26 C27 C28 0.1 no . . . . C26 C27 C28 C29 -0.2 no . . . . C27 C28 C29 C30 0.3 no . . . . C28 C29 C30 C25 -0.3 no . . . . C28 C29 C30 C31 179.4 no . . . . C25 C30 C31 C32 -0.0 no . . . . C29 C30 C31 C32 -179.7 no . . . . C30 C31 C32 C19 179.5 no . . . . C30 C31 C32 C23 -0.3 no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F1 O1 2.756(4) no . . F1 O3 3.558(3) no . . F1 C12 3.025(4) no . . F2 O1 3.203(4) no . . F2 O2 3.454(3) no . . F2 O3 2.957(3) no . . F2 C12 2.804(4) no . . F3 O3 2.644(3) no . . F4 O4 2.713(4) no . . F4 O6 3.570(3) no . . F4 C16 3.039(4) no . . F5 O4 2.997(4) no . . F5 O6 2.937(3) no . . F5 C16 2.817(5) no . . O1 O3 3.566(4) no . . O1 C1 3.295(5) no . . O1 C3 3.020(5) no . . O1 C14 2.864(5) no . . O1 C15 3.214(5) no . . O2 O3 2.735(4) no . . O2 C11 2.743(5) no . . O2 C14 3.468(5) no . . O4 O6 3.526(3) no . . O4 C2 3.160(4) no . . O4 C4 3.272(4) no . . O4 C11 3.391(4) no . . O4 C18 2.787(5) no . . O5 O6 2.641(4) no . . O5 C15 2.687(3) no . . O5 C18 3.555(5) no . . O6 F6 2.678(4) no . . C1 C4 2.781(6) no . . C2 C5 2.825(5) no . . C3 C10 2.810(4) no . . C5 C8 2.781(5) no . . C6 C9 2.781(7) no . . C7 C10 2.798(6) no . . C11 C15 2.981(5) no . . C19 C22 2.8202 no . . C20 C23 2.8222 no . . C21 C32 2.8221 no . . C23 C30 2.8219 no . . C24 C31 2.8098 no . . C25 C28 2.8222 no . . C25 C32 2.8219 no . . C26 C29 2.8202 no . . C27 C30 2.8221 no . . F1 O2 3.579(3) no . 1_565 F2 F3 3.337(5) no . 1_545 F2 F5 3.315(3) no . 1_655 F2 O5 3.591(4) no . 2_745 F2 O6 3.387(4) no . 1_655 F2 F6 3.050(4) no . 1_655 F3 F2 3.337(5) no . 1_565 F3 O2 3.592(4) no . 1_565 F3 O5 3.054(4) no . 2_755 F3 O6 3.351(4) no . 2_755 F3 C16 3.246(4) no . 2_755 F3 C17 3.337(5) no . 2_755 F3 F6 2.636(3) no . 1_665 F4 F5 3.578(4) no . 1_545 F4 O5 3.323(4) no . 1_545 F4 C7 3.287(4) no . 2_746 F4 C8 3.376(5) no . 2_746 F4 C15 3.544(4) no . 1_545 F4 C16 3.555(4) no . 1_545 F5 F2 3.315(3) no . 1_455 F5 F4 3.578(4) no . 1_565 O1 O2 3.499(3) no . 2_755 O2 F1 3.579(3) no . 1_545 O2 F3 3.592(4) no . 1_545 O2 O1 3.499(3) no . 2_745 O2 O2 3.397(3) no . 2_745 O2 O2 3.397(3) no . 2_755 O2 O3 3.532(4) no . 2_745 O2 C12 3.104(4) no . 2_745 O2 C13 3.157(4) no . 1_545 O2 C13 3.214(4) no . 2_745 O3 O2 3.532(4) no . 2_755 O3 O4 3.119(4) no . 2_755 O3 O5 2.792(4) no . 2_745 O3 C11 3.387(4) no . 2_755 O3 C15 3.396(4) no . 2_745 O3 C16 3.161(5) no . 2_755 O3 C17 3.360(5) no . 2_755 O4 O3 3.119(4) no . 2_745 O5 F2 3.591(4) no . 2_755 O5 F3 3.054(4) no . 2_745 O5 F4 3.323(4) no . 1_565 O5 O3 2.792(4) no . 2_755 O5 O6 2.939(3) no . 2_655 O5 C17 3.356(4) no . 1_565 O6 F2 3.387(4) no . 1_455 O6 F3 3.351(4) no . 2_745 O6 O5 2.939(3) no . 2_645 O6 O6 2.903(4) no . 2_645 O6 O6 2.903(4) no . 2_655 O6 C17 3.177(4) no . 2_655 O6 F6 3.468(3) no . 2_655 C1 C4 3.581(6) no . 1_545 C4 C1 3.581(6) no . 1_565 C6 C9 3.483(7) no . 1_565 C7 F4 3.287(4) no . 2_756 C8 F4 3.376(5) no . 2_756 C9 C6 3.483(7) no . 1_545 C11 O3 3.387(4) no . 2_745 C12 O2 3.104(4) no . 2_755 C13 O2 3.157(4) no . 1_565 C13 O2 3.214(4) no . 2_755 C15 F4 3.544(4) no . 1_565 C15 O3 3.396(4) no . 2_755 C16 F3 3.246(4) no . 2_745 C16 F4 3.555(4) no . 1_565 C16 O3 3.161(5) no . 2_745 C17 F3 3.337(5) no . 2_745 C17 O3 3.360(5) no . 2_745 C17 O5 3.356(4) no . 1_545 C17 O6 3.177(4) no . 2_645 F6 F2 3.050(4) no . 1_455 F6 F3 2.636(3) no . 1_445 F6 O6 3.468(3) no . 2_645 F1 H13 2.5044 no . . F2 H3A 2.8583 no . . F2 H13 3.1713 no . . F3 H3A 3.0340 no . . F3 H13 2.6514 no . . F4 H17 2.5116 no . . F5 H6A 3.4492 no . . F5 H17 3.1892 no . . O1 H1 3.4674 no . . O1 H13 2.5324 no . . O1 H15B 2.5813 no . . O2 H3A 2.4547 no . . O2 H11A 2.7366 no . . O2 H11B 2.7469 no . . O2 H13 3.0102 no . . O4 H4 3.3734 no . . O4 H11B 2.8019 no . . O4 H17 2.6839 no . . O5 H6A 3.3608 no . . O5 H15A 2.5791 no . . O5 H15B 2.7649 no . . O5 H17 2.9264 no . . C1 H9 2.6796 no . . C1 H11A 2.5688 no . . C1 H11B 3.1891 no . . C2 H4 3.2686 no . . C2 H15A 3.3448 no . . C2 H15B 2.7251 no . . C3 H1 3.2455 no . . C3 H11A 3.3342 no . . C3 H11B 2.7253 no . . C4 H6 2.6584 no . . C4 H15A 2.5510 no . . C4 H15B 3.2043 no . . C5 H1 3.2742 no . . C5 H7 3.2483 no . . C5 H9 3.2740 no . . C6 H4 2.6549 no . . C6 H8 3.2195 no . . C7 H9 3.2349 no . . C8 H6 3.2267 no . . C9 H1 2.6675 no . . C9 H7 3.2301 no . . C10 H4 3.2765 no . . C10 H6 3.2818 no . . C10 H8 3.2516 no . . C11 H1 2.6248 no . . C11 H15B 2.6817 no . . C12 H3A 2.4473 no . . C12 H11A 2.6528 no . . C12 H11B 2.6720 no . . C12 H15B 3.3859 no . . C14 H3A 2.6833 no . . C15 H4 2.6041 no . . C15 H11B 2.7435 no . . C16 H6A 3.0343 no . . C16 H15A 2.5746 no . . C16 H15B 2.6833 no . . C18 H6A 2.7132 no . . F6 H6A 2.6346 no . . F6 H17 2.6506 no . . H3A H13 2.5803 no . . H6A H17 2.0517 no . . H1 H9 2.5201 no . . H1 H11A 2.3514 no . . H1 H11B 3.3874 no . . H4 H6 2.4981 no . . H4 H15A 2.3295 no . . H4 H15B 3.4073 no . . H6 H7 2.2807 no . . H7 H8 2.3159 no . . H8 H9 2.2799 no . . H11B H15B 2.4310 no . . C19 H21 3.2612 no . . C19 H31 2.6444 no . . H19 H20 2.2913 no . . H19 C21 3.2708 no . . H19 C23 3.3033 no . . H19 C31 2.6585 no . . H19 H31 2.4887 no . . C20 H22 3.2707 no . . H20 H21 2.3540 no . . H20 C22 3.2613 no . . H20 C32 3.2768 no . . H21 H22 2.2913 no . . H21 C23 3.2768 no . . C22 H24 2.6443 no . . H22 C24 2.6585 no . . H22 H24 2.4887 no . . H22 C32 3.3031 no . . C23 H31 3.2799 no . . C24 H26 2.6584 no . . H24 C26 2.6441 no . . H24 H26 2.4885 no . . H24 C30 3.2797 no . . H24 C32 3.2797 no . . C25 H27 3.2768 no . . C25 H29 3.3031 no . . C25 H31 3.2798 no . . C26 H28 3.2614 no . . H26 H27 2.2913 no . . H26 C28 3.2709 no . . H26 C30 3.3031 no . . C27 H29 3.2708 no . . H27 H28 2.3542 no . . H27 C29 3.2613 no . . H28 H29 2.2914 no . . H28 C30 3.2769 no . . C29 H31 2.6442 no . . H29 C31 2.6584 no . . H29 H31 2.4885 no . . F1 H11A 2.8453 no . 1_565 F2 H6A 3.4328 no . 1_655 F3 H6A 3.4714 no . 1_665 F3 H6A 3.4144 no . 2_755 F3 H17 2.9325 no . 2_755 F4 H4 3.2899 no . 1_545 F4 H7 2.6396 no . 2_746 F4 H8 2.8103 no . 2_746 F4 H15A 2.7183 no . 1_545 F5 H7 3.0052 no . 2_746 F5 H8 3.3572 no . 2_756 O1 H11A 3.4079 no . 1_565 O2 H13 2.2426 no . 1_545 O2 H13 2.6762 no . 2_745 O2 H15B 2.9465 no . 2_745 O3 H11B 2.4403 no . 2_755 O3 H15A 2.9900 no . 2_745 O3 H15B 2.9479 no . 2_745 O3 H15B 3.4521 no . 2_755 O3 H17 2.6779 no . 2_755 O4 H3A 3.5360 no . 2_745 O4 H3A 3.4193 no . 2_755 O4 H15A 3.3893 no . 1_545 O5 H3A 2.0765 no . 2_755 O5 H6A 2.2612 no . 2_655 O5 H17 2.4489 no . 1_565 O6 H6A 3.3348 no . 2_645 O6 H6A 2.1857 no . 2_655 O6 H17 2.6139 no . 2_655 C1 H4 3.4156 no . 1_545 C2 H4 3.5789 no . 1_545 C3 H11A 3.5543 no . 1_565 C4 H1 3.3998 no . 1_565 C4 H6 3.5333 no . 2_746 C4 H7 3.5826 no . 2_746 C5 H1 3.5487 no . 1_565 C5 H6 2.9552 no . 2_746 C6 H6 2.7419 no . 2_746 C6 H9 3.2668 no . 1_565 C7 H4 3.2102 no . 2_746 C7 H6 3.1001 no . 2_746 C7 H9 3.4122 no . 1_565 C8 H4 3.4987 no . 2_746 C8 H6 3.5802 no . 2_746 C9 H6 3.2698 no . 1_545 C10 H6 3.4661 no . 1_545 C10 H6 3.5054 no . 2_746 C11 H15A 3.3658 no . 1_545 C11 H15B 3.5120 no . 1_545 C12 H13 3.2620 no . 1_545 C12 H13 3.1677 no . 2_745 C13 H11B 3.2748 no . 2_755 C15 H3A 2.8894 no . 2_755 C15 H11A 3.5196 no . 1_565 C15 H11B 3.2717 no . 1_565 C16 H3A 3.5889 no . 2_745 C16 H3A 3.0151 no . 2_755 C16 H6A 2.9786 no . 2_655 C16 H17 3.4417 no . 1_565 C17 H3A 3.4608 no . 2_745 C17 H6A 3.2799 no . 2_645 C17 H6A 3.1221 no . 2_655 C18 H7 3.3934 no . 2_746 C18 H8 3.5643 no . 2_746 F6 H6A 3.3954 no . 2_645 F6 H8 3.5688 no . 2_746 F6 H19 3.4857 no . . H3A O4 3.4193 no . 2_745 H3A O4 3.5360 no . 2_755 H3A O5 2.0765 no . 2_745 H3A C15 2.8894 no . 2_745 H3A C16 3.0151 no . 2_745 H3A C16 3.5889 no . 2_755 H3A C17 3.4608 no . 2_755 H3A H11B 2.8399 no . 2_755 H3A H15A 2.6295 no . 2_745 H3A H15B 2.4414 no . 2_745 H3A H17 2.6299 no . 2_755 H6A F2 3.4328 no . 1_455 H6A F3 3.4714 no . 1_445 H6A F3 3.4144 no . 2_745 H6A O5 2.2612 no . 2_645 H6A O6 2.1857 no . 2_645 H6A O6 3.3348 no . 2_655 H6A C16 2.9786 no . 2_645 H6A C17 3.1221 no . 2_645 H6A C17 3.2799 no . 2_655 H6A F6 3.3954 no . 2_655 H6A H6A 2.7037 no . 2_645 H6A H6A 2.7037 no . 2_655 H6A H17 2.5717 no . 2_655 H1 C4 3.3998 no . 1_545 H1 C5 3.5487 no . 1_545 H1 H4 3.4832 no . 1_545 H4 F4 3.2899 no . 1_565 H4 C1 3.4156 no . 1_565 H4 C2 3.5789 no . 1_565 H4 C7 3.2102 no . 2_756 H4 C8 3.4987 no . 2_756 H4 H1 3.4832 no . 1_565 H4 H7 3.0871 no . 2_756 H4 H8 3.5433 no . 2_756 H6 C4 3.5333 no . 2_756 H6 C5 2.9552 no . 2_756 H6 C6 2.7419 no . 2_756 H6 C7 3.1001 no . 2_756 H6 C8 3.5802 no . 2_756 H6 C9 3.2698 no . 1_565 H6 C10 3.4661 no . 1_565 H6 C10 3.5054 no . 2_756 H6 H6 2.9549 no . 2_746 H6 H6 2.9549 no . 2_756 H6 H7 3.5132 no . 2_756 H6 H9 3.3112 no . 1_565 H7 F4 2.6396 no . 2_756 H7 F5 3.0052 no . 2_756 H7 C4 3.5826 no . 2_756 H7 C18 3.3934 no . 2_756 H7 H4 3.0871 no . 2_746 H7 H6 3.5132 no . 2_746 H7 H9 3.5341 no . 1_565 H8 F4 2.8103 no . 2_756 H8 F5 3.3572 no . 2_746 H8 C18 3.5643 no . 2_756 H8 F6 3.5688 no . 2_756 H8 H4 3.5433 no . 2_746 H9 C6 3.2668 no . 1_545 H9 C7 3.4122 no . 1_545 H9 H6 3.3112 no . 1_545 H9 H7 3.5341 no . 1_545 H11A F1 2.8453 no . 1_545 H11A O1 3.4079 no . 1_545 H11A C3 3.5543 no . 1_545 H11A C15 3.5196 no . 1_545 H11A H13 3.1213 no . 1_545 H11A H15A 3.3556 no . 1_545 H11A H15B 3.1762 no . 1_545 H11B O3 2.4403 no . 2_745 H11B C13 3.2748 no . 2_745 H11B C15 3.2717 no . 1_545 H11B H3A 2.8399 no . 2_745 H11B H13 3.1143 no . 2_745 H11B H15A 2.7784 no . 1_545 H11B H15B 2.9784 no . 1_545 H13 O2 2.2426 no . 1_565 H13 O2 2.6762 no . 2_755 H13 C12 3.2620 no . 1_565 H13 C12 3.1677 no . 2_755 H13 H11A 3.1213 no . 1_565 H13 H11B 3.1143 no . 2_755 H13 H15B 3.5502 no . 2_755 H15A F4 2.7183 no . 1_565 H15A O3 2.9900 no . 2_755 H15A O4 3.3893 no . 1_565 H15A C11 3.3658 no . 1_565 H15A H3A 2.6295 no . 2_755 H15A H11A 3.3556 no . 1_565 H15A H11B 2.7784 no . 1_565 H15A H17 3.4018 no . 1_565 H15B O2 2.9465 no . 2_755 H15B O3 3.4521 no . 2_745 H15B O3 2.9479 no . 2_755 H15B C11 3.5120 no . 1_565 H15B H3A 2.4414 no . 2_755 H15B H11A 3.1762 no . 1_565 H15B H11B 2.9784 no . 1_565 H15B H13 3.5502 no . 2_745 H17 F3 2.9325 no . 2_745 H17 O3 2.6779 no . 2_745 H17 O5 2.4489 no . 1_545 H17 O6 2.6139 no . 2_645 H17 C16 3.4417 no . 1_545 H17 H3A 2.6299 no . 2_745 H17 H6A 2.5717 no . 2_645 H17 H15A 3.4018 no . 1_545 H19 F6 3.4857 no . . #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O3 H3A O2 . . . 2.735(4) 0.820 2.455 101.2 no O3 H3A O5 . . 2_745 2.792(4) 0.820 2.077 145.7 no O6 H6A O5 . . 2_645 2.939(3) 0.820 2.261 140.2 no O6 H6A O6 . . 2_645 2.903(4) 0.820 2.186 146.2 no data_HS008_Quenching _database_code_depnum_ccdc_archive 'CCDC 837540' #TrackingRef 'web_deposit_cif_file_1_ToshimasaKatagiri_1312169855.Quenching.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C18 H14 F6 O6' _chemical_formula_moiety 'C18 H14 F6 O6' _chemical_formula_weight 440.30 _chemical_melting_point ? _chemical_absolute_configuration rm #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,-Z #------------------------------------------------------------------------------ _cell_length_a 13.308(6) _cell_length_b 5.176(3) _cell_length_c 15.272(7) _cell_angle_alpha 90.0000 _cell_angle_beta 98.749(10) _cell_angle_gamma 90.0000 _cell_volume 1039.7(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 4694 _cell_measurement_theta_min 3.10 _cell_measurement_theta_max 27.72 _cell_measurement_temperature 298 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 5.100 _exptl_crystal_size_mid 0.015 _exptl_crystal_size_min 0.015 _exptl_crystal_density_diffrn 1.406 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448.00 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_absorpt_correction_T_min 0.108 _exptl_absorpt_correction_T_max 0.979 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 298 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 9888 _diffrn_reflns_av_R_equivalents 0.1008 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2635 _reflns_number_gt 1219 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1057 _refine_ls_wR_factor_ref 0.3487 _refine_ls_number_restraints 264 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2635 _refine_ls_number_parameters 273 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.390 _refine_diff_density_min -0.280 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.0171 0.0103 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 F1 F -0.1449(6) 0.1195(19) 0.1985(5) 0.116(3) Uani 1.0 2 d . . . F2 F -0.2378(7) 0.445(3) 0.1599(6) 0.132(3) Uani 1.0 2 d . . . F3 F -0.2755(7) 0.075(3) 0.1014(6) 0.135(3) Uani 1.0 2 d . . . F4 F 0.4573(7) 0.810(2) 0.2460(6) 0.125(3) Uani 1.0 2 d . . . F5 F 0.5418(6) 0.459(3) 0.2338(5) 0.123(3) Uani 1.0 2 d . . . F6 F 0.5864(6) 0.8120(19) 0.1795(6) 0.122(3) Uani 1.0 2 d . . . O1 O -0.0035(5) 0.4633(15) 0.1509(5) 0.0757(17) Uani 1.0 2 d . . . O2 O -0.0692(6) 0.7064(13) 0.0347(5) 0.0792(18) Uani 1.0 2 d . . . O3 O -0.2037(5) 0.3269(14) -0.0238(5) 0.0780(19) Uani 1.0 2 d . . . O4 O 0.3101(5) 0.4718(14) 0.1802(5) 0.0744(16) Uani 1.0 2 d . . . O5 O 0.3478(5) 0.2200(14) 0.0706(5) 0.0792(19) Uani 1.0 2 d . . . O6 O 0.4996(6) 0.5224(13) 0.0438(5) 0.0779(18) Uani 1.0 2 d . . . C1 C 0.0930(10) 0.697(4) 0.3482(9) 0.103(3) Uani 1.0 2 d . . . C2 C 0.1192(7) 0.592(3) 0.2738(7) 0.080(2) Uani 1.0 2 d . . . C3 C 0.1959(8) 0.399(3) 0.2811(7) 0.085(3) Uani 1.0 2 d . . . C4 C 0.2379(10) 0.318(4) 0.3661(9) 0.111(3) Uani 1.0 2 d . . . C5 C 0.2060(13) 0.434(5) 0.4409(9) 0.129(4) Uani 1.0 2 d . . . C6 C 0.2464(16) 0.361(6) 0.5312(11) 0.158(5) Uani 1.0 2 d . . . C7 C 0.2205(18) 0.491(7) 0.6008(12) 0.167(5) Uani 1.0 2 d . . . C8 C 0.1481(17) 0.690(6) 0.5907(12) 0.165(5) Uani 1.0 2 d . . . C9 C 0.1098(14) 0.748(6) 0.5110(11) 0.151(4) Uani 1.0 2 d . . . C10 C 0.1360(12) 0.626(5) 0.4320(9) 0.125(4) Uani 1.0 2 d . . . C11 C 0.0672(8) 0.675(3) 0.1856(7) 0.082(3) Uani 1.0 2 d . . . C12 C -0.0692(7) 0.5113(18) 0.0782(6) 0.0640(19) Uani 1.0 2 d . . . C13 C -0.1403(7) 0.291(2) 0.0551(7) 0.0677(19) Uani 1.0 2 d . . . C14 C -0.2014(10) 0.235(4) 0.1267(9) 0.099(3) Uani 1.0 2 d . . . C15 C 0.2342(8) 0.289(3) 0.2003(8) 0.082(3) Uani 1.0 2 d . . . C16 C 0.3597(7) 0.4139(19) 0.1160(7) 0.0645(18) Uani 1.0 2 d . . . C17 C 0.4397(8) 0.614(2) 0.1061(7) 0.074(2) Uani 1.0 2 d . . . C18 C 0.5087(10) 0.670(3) 0.1916(9) 0.099(3) Uani 1.0 2 d . . . H1 H 0.0431 0.8239 0.3421 0.1234 Uiso 1.0 2 calc R . . H3 H -0.2289 0.4716 -0.0246 0.0936 Uiso 1.0 2 calc R . . H4 H 0.2867 0.1873 0.3733 0.1335 Uiso 1.0 2 calc R . . H6 H 0.5252 0.6453 0.0214 0.0935 Uiso 1.0 2 calc R . . H6A H 0.2909 0.2218 0.5412 0.1899 Uiso 1.0 2 calc R . . H7 H 0.2517 0.4473 0.6576 0.1999 Uiso 1.0 2 calc R . . H8 H 0.1289 0.7757 0.6391 0.1986 Uiso 1.0 2 calc R . . H9 H 0.0613 0.8784 0.5032 0.1808 Uiso 1.0 2 calc R . . H11A H 0.1164 0.7057 0.1459 0.0979 Uiso 1.0 2 calc R . . H11B H 0.0296 0.8339 0.1907 0.0979 Uiso 1.0 2 calc R . . H13 H -0.0990 0.1371 0.0485 0.0812 Uiso 1.0 2 calc R . . H15A H 0.2641 0.1197 0.2132 0.0978 Uiso 1.0 2 calc R . . H15B H 0.1792 0.2740 0.1510 0.0978 Uiso 1.0 2 calc R . . H17 H 0.4060 0.7743 0.0837 0.0884 Uiso 1.0 2 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 F1 0.128(5) 0.127(6) 0.092(4) -0.024(5) 0.011(4) 0.028(5) F2 0.125(5) 0.139(6) 0.144(6) 0.004(5) 0.063(5) -0.003(6) F3 0.114(5) 0.154(7) 0.132(6) -0.068(5) 0.005(4) 0.022(5) F4 0.135(5) 0.127(6) 0.117(5) -0.036(5) 0.034(4) -0.044(5) F5 0.112(5) 0.139(6) 0.106(5) -0.008(5) -0.020(4) 0.023(5) F6 0.101(4) 0.127(6) 0.137(6) -0.055(5) 0.017(4) -0.020(5) O1 0.073(4) 0.068(4) 0.082(4) -0.012(4) 0.001(3) -0.000(4) O2 0.088(4) 0.056(4) 0.091(5) -0.004(4) 0.007(4) 0.003(3) O3 0.077(4) 0.063(4) 0.087(4) 0.006(4) -0.011(3) -0.007(4) O4 0.077(4) 0.064(4) 0.084(4) -0.001(4) 0.018(3) -0.002(3) O5 0.079(4) 0.063(4) 0.097(5) -0.004(4) 0.017(4) -0.008(4) O6 0.085(4) 0.060(4) 0.093(5) -0.005(3) 0.028(4) 0.005(4) C1 0.090(6) 0.132(7) 0.091(5) -0.024(6) 0.027(5) -0.024(6) C2 0.069(4) 0.099(5) 0.074(4) -0.025(4) 0.020(4) -0.012(4) C3 0.070(5) 0.107(6) 0.079(5) -0.023(4) 0.012(4) -0.001(5) C4 0.099(6) 0.145(8) 0.086(5) -0.020(6) 0.002(5) 0.004(6) C5 0.131(7) 0.174(8) 0.079(5) -0.026(6) 0.008(5) -0.002(6) C6 0.175(9) 0.205(11) 0.089(6) -0.015(9) 0.004(7) 0.002(8) C7 0.190(10) 0.221(11) 0.084(6) -0.007(9) 0.008(8) 0.001(8) C8 0.178(10) 0.219(11) 0.097(6) -0.011(9) 0.013(8) -0.007(9) C9 0.154(8) 0.202(10) 0.097(6) -0.019(8) 0.022(7) -0.017(8) C10 0.114(6) 0.172(8) 0.090(5) -0.029(6) 0.019(5) -0.018(6) C11 0.077(5) 0.078(5) 0.086(5) -0.021(5) 0.002(4) -0.009(5) C12 0.071(4) 0.051(4) 0.070(5) 0.001(4) 0.013(4) -0.002(4) C13 0.064(4) 0.058(4) 0.078(5) 0.000(4) 0.003(3) 0.000(4) C14 0.091(5) 0.105(6) 0.103(5) -0.024(4) 0.018(4) 0.010(5) C15 0.073(5) 0.080(6) 0.092(5) -0.010(5) 0.013(4) -0.003(5) C16 0.066(4) 0.054(4) 0.073(5) 0.009(4) 0.009(4) 0.002(4) C17 0.081(5) 0.056(4) 0.085(5) 0.001(4) 0.015(4) 0.005(4) C18 0.094(5) 0.103(6) 0.098(5) -0.025(5) 0.013(4) -0.007(5) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C14 1.370(16) yes . . F2 C14 1.32(2) yes . . F3 C14 1.300(17) yes . . F4 C18 1.361(17) yes . . F5 C18 1.311(18) yes . . F6 C18 1.303(16) yes . . O1 C11 1.489(13) yes . . O1 C12 1.329(11) yes . . O2 C12 1.209(12) yes . . O3 C13 1.375(11) yes . . O4 C15 1.451(14) yes . . O4 C16 1.297(13) yes . . O5 C16 1.217(12) yes . . O6 C17 1.413(14) yes . . C1 C2 1.351(18) yes . . C1 C10 1.371(19) yes . . C2 C3 1.418(17) yes . . C2 C11 1.483(14) yes . . C3 C4 1.399(17) yes . . C3 C15 1.516(17) yes . . C4 C5 1.41(3) yes . . C5 C6 1.45(3) yes . . C5 C10 1.36(3) yes . . C6 C7 1.35(4) yes . . C7 C8 1.40(4) yes . . C8 C9 1.28(3) yes . . C9 C10 1.45(3) yes . . C12 C13 1.491(13) yes . . C13 C14 1.486(18) yes . . C16 C17 1.509(14) yes . . C17 C18 1.506(16) yes . . O3 H3 0.820 no . . O6 H6 0.820 no . . C1 H1 0.930 no . . C4 H4 0.930 no . . C6 H6A 0.930 no . . C7 H7 0.930 no . . C8 H8 0.930 no . . C9 H9 0.930 no . . C11 H11A 0.970 no . . C11 H11B 0.970 no . . C13 H13 0.980 no . . C15 H15A 0.970 no . . C15 H15B 0.970 no . . C17 H17 0.980 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C11 O1 C12 117.4(8) yes . . . C15 O4 C16 117.4(8) yes . . . C2 C1 C10 123.6(15) yes . . . C1 C2 C3 119.4(11) yes . . . C1 C2 C11 120.2(11) yes . . . C3 C2 C11 120.5(10) yes . . . C2 C3 C4 117.9(12) yes . . . C2 C3 C15 121.9(10) yes . . . C4 C3 C15 120.2(12) yes . . . C3 C4 C5 119.6(15) yes . . . C4 C5 C6 122.9(19) yes . . . C4 C5 C10 121.2(14) yes . . . C6 C5 C10 115.8(17) yes . . . C5 C6 C7 121(3) yes . . . C6 C7 C8 122.3(18) yes . . . C7 C8 C9 116(3) yes . . . C8 C9 C10 125(3) yes . . . C1 C10 C5 118.2(15) yes . . . C1 C10 C9 122.9(19) yes . . . C5 C10 C9 119.0(15) yes . . . O1 C11 C2 106.9(9) yes . . . O1 C12 O2 124.0(9) yes . . . O1 C12 C13 111.6(8) yes . . . O2 C12 C13 124.4(8) yes . . . O3 C13 C12 112.6(8) yes . . . O3 C13 C14 109.9(9) yes . . . C12 C13 C14 111.8(10) yes . . . F1 C14 F2 104.0(11) yes . . . F1 C14 F3 105.0(13) yes . . . F1 C14 C13 112.2(10) yes . . . F2 C14 F3 109.4(12) yes . . . F2 C14 C13 113.4(13) yes . . . F3 C14 C13 112.2(11) yes . . . O4 C15 C3 104.9(9) yes . . . O4 C16 O5 125.8(9) yes . . . O4 C16 C17 111.4(9) yes . . . O5 C16 C17 122.7(10) yes . . . O6 C17 C16 108.5(9) yes . . . O6 C17 C18 108.4(9) yes . . . C16 C17 C18 113.1(10) yes . . . F4 C18 F5 107.6(11) yes . . . F4 C18 F6 105.7(12) yes . . . F4 C18 C17 109.6(10) yes . . . F5 C18 F6 108.9(11) yes . . . F5 C18 C17 112.3(12) yes . . . F6 C18 C17 112.3(11) yes . . . C13 O3 H3 109.475 no . . . C17 O6 H6 109.476 no . . . C2 C1 H1 118.180 no . . . C10 C1 H1 118.173 no . . . C3 C4 H4 120.208 no . . . C5 C4 H4 120.194 no . . . C5 C6 H6A 119.409 no . . . C7 C6 H6A 119.416 no . . . C6 C7 H7 118.870 no . . . C8 C7 H7 118.871 no . . . C7 C8 H8 121.851 no . . . C9 C8 H8 121.857 no . . . C8 C9 H9 117.336 no . . . C10 C9 H9 117.345 no . . . O1 C11 H11A 110.334 no . . . O1 C11 H11B 110.339 no . . . C2 C11 H11A 110.340 no . . . C2 C11 H11B 110.348 no . . . H11A C11 H11B 108.567 no . . . O3 C13 H13 107.417 no . . . C12 C13 H13 107.416 no . . . C14 C13 H13 107.419 no . . . O4 C15 H15A 110.763 no . . . O4 C15 H15B 110.763 no . . . C3 C15 H15A 110.761 no . . . C3 C15 H15B 110.764 no . . . H15A C15 H15B 108.846 no . . . O6 C17 H17 108.909 no . . . C16 C17 H17 108.914 no . . . C18 C17 H17 108.916 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C11 O1 C12 O2 6.7(14) no . . . . C11 O1 C12 C13 -175.5(7) no . . . . C12 O1 C11 C2 170.4(8) no . . . . C15 O4 C16 O5 0.6(13) no . . . . C15 O4 C16 C17 -176.8(7) no . . . . C16 O4 C15 C3 176.0(7) no . . . . C2 C1 C10 C5 -2(3) no . . . . C2 C1 C10 C9 177.5(14) no . . . . C10 C1 C2 C3 -1(3) no . . . . C10 C1 C2 C11 178.6(14) no . . . . C1 C2 C3 C4 3.0(17) no . . . . C1 C2 C3 C15 -175.3(11) no . . . . C1 C2 C11 O1 -105.3(13) no . . . . C3 C2 C11 O1 73.8(13) no . . . . C11 C2 C3 C4 -176.2(10) no . . . . C11 C2 C3 C15 5.5(17) no . . . . C2 C3 C4 C5 -2(2) no . . . . C2 C3 C15 O4 83.3(12) no . . . . C4 C3 C15 O4 -94.9(14) no . . . . C15 C3 C4 C5 176.1(11) no . . . . C3 C4 C5 C6 -179.6(14) no . . . . C3 C4 C5 C10 -1(3) no . . . . C4 C5 C6 C7 174.2(18) no . . . . C4 C5 C10 C1 3(3) no . . . . C4 C5 C10 C9 -176.8(16) no . . . . C6 C5 C10 C1 -178.0(17) no . . . . C6 C5 C10 C9 2(3) no . . . . C10 C5 C6 C7 -5(3) no . . . . C5 C6 C7 C8 5(4) no . . . . C6 C7 C8 C9 -2(4) no . . . . C7 C8 C9 C10 -1(4) no . . . . C8 C9 C10 C1 -180(3) no . . . . C8 C9 C10 C5 0(4) no . . . . O1 C12 C13 O3 -175.1(8) no . . . . O1 C12 C13 C14 60.6(10) no . . . . O2 C12 C13 O3 2.8(14) no . . . . O2 C12 C13 C14 -121.5(10) no . . . . O3 C13 C14 F1 160.7(10) no . . . . O3 C13 C14 F2 -81.8(11) no . . . . O3 C13 C14 F3 42.9(14) no . . . . C12 C13 C14 F1 -73.4(13) no . . . . C12 C13 C14 F2 44.1(12) no . . . . C12 C13 C14 F3 168.7(9) no . . . . O4 C16 C17 O6 172.1(7) no . . . . O4 C16 C17 C18 51.8(10) no . . . . O5 C16 C17 O6 -5.4(12) no . . . . O5 C16 C17 C18 -125.7(9) no . . . . O6 C17 C18 F4 166.9(9) no . . . . O6 C17 C18 F5 -73.5(12) no . . . . O6 C17 C18 F6 49.7(13) no . . . . C16 C17 C18 F4 -72.7(13) no . . . . C16 C17 C18 F5 46.9(14) no . . . . C16 C17 C18 F6 170.1(9) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F1 O1 2.767(12) no . . F1 O3 3.533(10) no . . F1 C12 3.011(13) no . . F2 O1 3.144(11) no . . F2 O2 3.438(13) no . . F2 O3 2.972(12) no . . F2 C12 2.749(14) no . . F3 O3 2.610(12) no . . F4 O4 2.704(11) no . . F4 O6 3.549(12) no . . F4 C16 3.007(13) no . . F5 O4 3.068(10) no . . F5 O5 3.529(10) no . . F5 O6 2.889(11) no . . F5 C16 2.800(11) no . . F6 O6 2.674(11) no . . O1 O3 3.543(9) no . . O1 C1 3.318(15) no . . O1 C3 3.081(12) no . . O1 C14 2.859(15) no . . O1 C15 3.265(12) no . . O2 O3 2.716(10) no . . O2 C11 2.711(12) no . . O2 C14 3.431(17) no . . O4 O6 3.517(11) no . . O4 C2 3.160(13) no . . O4 C4 3.232(16) no . . O4 C11 3.413(13) no . . O4 C18 2.817(15) no . . O5 O6 2.637(10) no . . O5 C15 2.692(14) no . . O5 C18 3.497(15) no . . C1 C4 2.74(3) no . . C2 C5 2.760(18) no . . C3 C10 2.81(2) no . . C3 C16 3.575(15) no . . C5 C8 2.85(3) no . . C6 C9 2.69(4) no . . C7 C10 2.74(3) no . . C11 C15 2.973(16) no . . F1 O2 3.551(11) no . 1_545 F1 C7 3.43(3) no . 2_546 F1 C8 3.25(2) no . 2_546 F2 F3 3.398(17) no . 1_565 F2 F5 3.300(13) no . 1_455 F2 F6 3.062(14) no . 1_455 F3 F2 3.398(17) no . 1_545 F3 F6 2.707(13) no . 1_445 F3 O5 3.231(12) no . 2_545 F3 O6 3.447(11) no . 2_545 F3 C16 3.442(13) no . 2_545 F3 C17 3.570(13) no . 2_545 F4 F5 3.558(15) no . 1_565 F4 O5 3.553(12) no . 1_565 F5 F2 3.300(13) no . 1_655 F5 F4 3.558(15) no . 1_545 F5 F6 3.522(15) no . 1_545 F6 F2 3.062(14) no . 1_655 F6 F3 2.707(13) no . 1_665 F6 F5 3.522(15) no . 1_565 F6 O6 3.598(12) no . 2_655 O1 O2 3.402(11) no . 2_545 O2 F1 3.551(11) no . 1_565 O2 O1 3.402(11) no . 2_555 O2 O2 3.436(10) no . 2_545 O2 O2 3.436(10) no . 2_555 O2 C12 3.134(13) no . 2_555 O2 C13 3.197(13) no . 1_565 O2 C13 3.318(13) no . 2_555 O3 O4 3.171(10) no . 2_545 O3 O5 2.812(10) no . 2_555 O3 C11 3.375(14) no . 2_545 O3 C15 3.581(14) no . 2_555 O3 C16 3.158(12) no . 2_545 O3 C17 3.385(12) no . 2_545 O4 O3 3.171(10) no . 2_555 O5 F3 3.231(12) no . 2_555 O5 F4 3.553(12) no . 1_545 O5 O3 2.812(10) no . 2_545 O5 O6 3.050(11) no . 2_645 O5 C17 3.381(13) no . 1_545 O6 F3 3.447(11) no . 2_555 O6 F6 3.598(12) no . 2_645 O6 O5 3.050(11) no . 2_655 O6 O6 2.914(10) no . 2_645 O6 O6 2.914(10) no . 2_655 O6 C17 3.305(13) no . 2_645 C7 F1 3.43(3) no . 2_556 C8 F1 3.25(2) no . 2_556 C11 O3 3.375(14) no . 2_555 C12 O2 3.134(13) no . 2_545 C13 O2 3.197(13) no . 1_545 C13 O2 3.318(13) no . 2_545 C15 O3 3.581(14) no . 2_545 C16 F3 3.442(13) no . 2_555 C16 O3 3.158(12) no . 2_555 C17 F3 3.570(13) no . 2_555 C17 O3 3.385(12) no . 2_555 C17 O5 3.381(13) no . 1_565 C17 O6 3.305(13) no . 2_655 F1 H13 2.4610 no . . F2 H3 2.8404 no . . F2 H13 3.1316 no . . F3 H3 2.9415 no . . F3 H13 2.6165 no . . F4 H17 2.4762 no . . F5 H6 3.3587 no . . F5 H17 3.1501 no . . F6 H6 2.5766 no . . F6 H17 2.6222 no . . O1 H1 3.4414 no . . O1 H13 2.5119 no . . O1 H15B 2.6212 no . . O2 H3 2.4963 no . . O2 H11A 2.7761 no . . O2 H11B 2.6241 no . . O2 H13 2.9850 no . . O4 H4 3.3530 no . . O4 H11A 2.8235 no . . O4 H17 2.6123 no . . O5 H6 3.3952 no . . O5 H15A 2.6433 no . . O5 H15B 2.7302 no . . O5 H17 2.9705 no . . C1 H9 2.6410 no . . C1 H11A 3.1512 no . . C1 H11B 2.5260 no . . C2 H4 3.2602 no . . C2 H15A 3.3306 no . . C2 H15B 2.7052 no . . C3 H1 3.2258 no . . C3 H11A 2.6887 no . . C3 H11B 3.3056 no . . C4 H6A 2.7053 no . . C4 H15A 2.6206 no . . C4 H15B 3.2660 no . . C5 H1 3.1711 no . . C5 H7 3.2729 no . . C5 H9 3.2353 no . . C6 H4 2.7028 no . . C6 H8 3.2485 no . . C7 H9 3.1262 no . . C8 H6A 3.2408 no . . C9 H1 2.6272 no . . C9 H7 3.1156 no . . C10 H4 3.2449 no . . C10 H6A 3.2185 no . . C10 H8 3.2715 no . . C11 H1 2.5773 no . . C11 H15B 2.6568 no . . C12 H3 2.4507 no . . C12 H11A 2.7221 no . . C12 H11B 2.6051 no . . C12 H15B 3.5441 no . . C14 H3 2.5906 no . . C15 H4 2.6795 no . . C15 H11A 2.7213 no . . C16 H6 3.0568 no . . C16 H15A 2.5904 no . . C16 H15B 2.6395 no . . C18 H6 2.6434 no . . H1 H9 2.4517 no . . H1 H11A 3.3453 no . . H1 H11B 2.2922 no . . H3 H13 2.5778 no . . H4 H6A 2.5619 no . . H4 H15A 2.4427 no . . H4 H15B 3.5059 no . . H6 H17 2.0797 no . . H6A H7 2.2537 no . . H7 H8 2.3443 no . . H8 H9 2.1986 no . . H11A H15B 2.3833 no . . F1 H1 3.4264 no . 1_545 F1 H7 2.9317 no . 2_546 F1 H8 2.5858 no . 2_546 F1 H11B 2.7709 no . 1_545 F2 H8 3.3075 no . 2_546 F3 H6 3.5348 no . 1_445 F3 H6 3.5779 no . 2_545 F3 H17 3.2515 no . 2_545 F4 H15A 3.0076 no . 1_565 F6 H7 3.1129 no . 2_656 O1 H11B 3.3310 no . 1_545 O2 H13 2.2794 no . 1_565 O2 H13 2.7601 no . 2_555 O2 H15B 3.0084 no . 2_555 O3 H11A 2.4259 no . 2_545 O3 H15A 3.2564 no . 2_555 O3 H15B 3.5024 no . 2_545 O3 H15B 3.0707 no . 2_555 O3 H17 2.7219 no . 2_545 O4 H3 3.5687 no . 2_545 O4 H3 3.5672 no . 2_555 O4 H15A 3.4590 no . 1_565 O5 H3 2.0759 no . 2_545 O5 H6 2.3885 no . 2_645 O5 H17 2.4322 no . 1_545 O6 H6 2.1937 no . 2_645 O6 H6 3.3758 no . 2_655 O6 H17 2.7858 no . 2_645 C1 H4 3.5962 no . 1_565 C2 H15A 3.5469 no . 1_565 C6 H9 3.4876 no . 1_545 C8 H1 3.4517 no . 2_546 C8 H6A 3.4919 no . 1_565 C8 H9 3.3477 no . 2_546 C9 H6A 3.4206 no . 1_565 C9 H9 2.9557 no . 2_546 C10 H9 3.2095 no . 2_546 C11 H15A 3.4645 no . 1_565 C11 H15B 3.5130 no . 1_565 C12 H13 3.2865 no . 1_565 C12 H13 3.2397 no . 2_555 C13 H11A 3.1655 no . 2_545 C14 H8 3.5649 no . 2_546 C15 H3 3.1384 no . 2_545 C15 H11A 3.4443 no . 1_545 C15 H11B 3.5858 no . 1_545 C16 H3 3.0788 no . 2_545 C16 H3 3.5459 no . 2_555 C16 H6 3.1088 no . 2_645 C16 H17 3.4171 no . 1_545 C17 H3 3.4325 no . 2_555 C17 H6 3.1887 no . 2_645 C17 H6 3.4428 no . 2_655 H1 F1 3.4264 no . 1_565 H1 C8 3.4517 no . 2_556 H1 H8 3.3151 no . 2_556 H3 O4 3.5672 no . 2_545 H3 O4 3.5687 no . 2_555 H3 O5 2.0759 no . 2_555 H3 C15 3.1384 no . 2_555 H3 C16 3.5459 no . 2_545 H3 C16 3.0788 no . 2_555 H3 C17 3.4325 no . 2_545 H3 H6 3.5644 no . 1_455 H3 H11A 2.9011 no . 2_545 H3 H15A 2.9485 no . 2_555 H3 H15B 2.6463 no . 2_555 H3 H17 2.6009 no . 2_545 H4 C1 3.5962 no . 1_545 H6 F3 3.5348 no . 1_665 H6 F3 3.5779 no . 2_555 H6 O5 2.3885 no . 2_655 H6 O6 3.3758 no . 2_645 H6 O6 2.1937 no . 2_655 H6 C16 3.1088 no . 2_655 H6 C17 3.4428 no . 2_645 H6 C17 3.1887 no . 2_655 H6 H3 3.5644 no . 1_655 H6 H6 2.7282 no . 2_645 H6 H6 2.7282 no . 2_655 H6 H17 2.7476 no . 2_645 H6A C8 3.4919 no . 1_545 H6A C9 3.4206 no . 1_545 H6A H9 3.5062 no . 1_545 H7 F1 2.9317 no . 2_556 H7 F6 3.1129 no . 2_646 H8 F1 2.5858 no . 2_556 H8 F2 3.3075 no . 2_556 H8 C14 3.5649 no . 2_556 H8 H1 3.3151 no . 2_546 H9 C6 3.4876 no . 1_565 H9 C8 3.3477 no . 2_556 H9 C9 2.9557 no . 2_556 H9 C10 3.2095 no . 2_556 H9 H6A 3.5062 no . 1_565 H9 H9 3.0526 no . 2_546 H9 H9 3.0526 no . 2_556 H11A O3 2.4259 no . 2_555 H11A C13 3.1655 no . 2_555 H11A C15 3.4443 no . 1_565 H11A H3 2.9011 no . 2_555 H11A H13 2.9639 no . 2_555 H11A H15A 2.9827 no . 1_565 H11A H15B 3.0553 no . 1_565 H11B F1 2.7709 no . 1_565 H11B O1 3.3310 no . 1_565 H11B C15 3.5858 no . 1_565 H11B H13 2.9970 no . 1_565 H11B H15A 3.4233 no . 1_565 H11B H15B 3.1441 no . 1_565 H13 O2 2.2794 no . 1_545 H13 O2 2.7601 no . 2_545 H13 C12 3.2865 no . 1_545 H13 C12 3.2397 no . 2_545 H13 H11A 2.9639 no . 2_545 H13 H11B 2.9970 no . 1_545 H15A F4 3.0076 no . 1_545 H15A O3 3.2564 no . 2_545 H15A O4 3.4590 no . 1_545 H15A C2 3.5469 no . 1_545 H15A C11 3.4645 no . 1_545 H15A H3 2.9485 no . 2_545 H15A H11A 2.9827 no . 1_545 H15A H11B 3.4233 no . 1_545 H15A H17 3.4364 no . 1_545 H15B O2 3.0084 no . 2_545 H15B O3 3.0707 no . 2_545 H15B O3 3.5024 no . 2_555 H15B C11 3.5130 no . 1_545 H15B H3 2.6463 no . 2_545 H15B H11A 3.0553 no . 1_545 H15B H11B 3.1441 no . 1_545 H17 F3 3.2515 no . 2_555 H17 O3 2.7219 no . 2_555 H17 O5 2.4322 no . 1_565 H17 O6 2.7858 no . 2_655 H17 C16 3.4171 no . 1_565 H17 H3 2.6009 no . 2_555 H17 H6 2.7476 no . 2_655 H17 H15A 3.4364 no . 1_565 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O3 H3 O2 . . . 2.716(10) 0.820 2.496 96.6 no O3 H3 O5 . . 2_555 2.812(10) 0.820 2.076 149.3 no O6 H6 O6 . . 2_655 2.914(10) 0.820 2.194 146.7 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================