# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr John Ripmeester' _publ_contact_author_address ; Steacie Institute for Molecular Sciences National Research Council Canada 100 Sussex Drive Ottawa Ontario K1A 0R6 CANADA ; _publ_contact_author_email JOHN.RIPMEESTER@NRC-CNRC.GC.CA _publ_section_title ; Electrostatic and short-range interactions compete in directing the structure of p-tert-butylcalix[4]arene inclusion compounds of fluorinated benzenes ; loop_ _publ_author_name 'John Ripmeester' 'Gary D. Enright' 'Konstantin A. Udachin' data_sadf1 _database_code_depnum_ccdc_archive 'CCDC 237575' _audit_creation_method SHELXL-97 _chemical_name_systematic ; p-tert-butyl-calix[4]arene*hexafluorobenzene ; _chemical_name_common p-tert-butyl-calix(4)arene*hexafluorobenzene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C56 H52 F12 O4' _chemical_formula_weight 1016.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 23.310(4) _cell_length_b 22.415(4) _cell_length_c 9.8489(16) _cell_angle_alpha 90.00 _cell_angle_beta 100.220(4) _cell_angle_gamma 90.00 _cell_volume 5064.4(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2112 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9827 _exptl_absorpt_correction_T_max 0.9982 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD Bruker Smart 1000' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14172 _diffrn_reflns_av_R_equivalents 0.0880 _diffrn_reflns_av_sigmaI/netI 0.0617 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 20.98 _reflns_number_total 2774 _reflns_number_gt 1780 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1067P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2774 _refine_ls_number_parameters 382 _refine_ls_number_restraints 123 _refine_ls_R_factor_all 0.1048 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1759 _refine_ls_wR_factor_gt 0.1528 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.018 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.003 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 O3 O 0.11512(9) 0.0000 0.5055(2) 0.0403(7) Uani 1 2 d S . . O1 O 0.26546(9) 0.0000 0.4265(2) 0.0388(7) Uani 1 2 d S . . O2 O 0.18989(7) 0.08213(7) 0.46592(14) 0.0400(5) Uani 1 1 d . . . C1 C 0.27543(13) 0.0000 0.2914(3) 0.0271(9) Uani 1 2 d S . . C2 C 0.28055(9) 0.05422(9) 0.2248(2) 0.0285(6) Uani 1 1 d . . . C3 C 0.29332(9) 0.05260(10) 0.0931(2) 0.0295(7) Uani 1 1 d . . . H3 H 0.2974 0.0887 0.0490 0.035 Uiso 1 1 calc R . . C4 C 0.30040(13) 0.0000 0.0225(3) 0.0304(10) Uani 1 2 d S . . C7 C 0.31716(15) 0.0000 -0.1200(3) 0.0386(11) Uani 1 2 d S . . C8 C 0.27290(10) 0.11358(9) 0.2955(2) 0.0319(7) Uani 1 1 d . . . H8A H 0.2859 0.1089 0.3941 0.038 Uiso 1 1 calc R . . H8B H 0.2977 0.1432 0.2632 0.038 Uiso 1 1 calc R . . C21 C 0.17034(10) 0.11821(9) 0.3513(2) 0.0312(7) Uani 1 1 d . . . C22 C 0.11271(10) 0.13665(10) 0.3236(2) 0.0327(7) Uani 1 1 d . . . C23 C 0.09680(10) 0.17675(10) 0.2171(2) 0.0355(7) Uani 1 1 d . . . H23 H 0.0584 0.1900 0.1989 0.043 Uiso 1 1 calc R . . C24 C 0.13483(10) 0.19827(10) 0.1362(2) 0.0328(7) Uani 1 1 d . . . C25 C 0.19160(10) 0.17684(9) 0.1639(2) 0.0314(7) Uani 1 1 d . . . H25 H 0.2179 0.1899 0.1095 0.038 Uiso 1 1 calc R . . C26 C 0.21078(9) 0.13658(9) 0.2700(2) 0.0283(7) Uani 1 1 d . . . C27 C 0.11451(10) 0.24409(10) 0.0214(2) 0.0373(7) Uani 1 1 d . . . C28 C 0.06748(10) 0.11397(10) 0.4066(2) 0.0380(8) Uani 1 1 d . . . H28A H 0.0861 0.1099 0.5024 0.046 Uiso 1 1 calc R . . H28B H 0.0369 0.1437 0.4025 0.046 Uiso 1 1 calc R . . C29 C 0.07548(11) 0.21291(11) -0.0989(3) 0.0508(9) Uani 1 1 d . . . H29A H 0.0430 0.1948 -0.0668 0.076 Uiso 1 1 calc R . . H29B H 0.0975 0.1827 -0.1362 0.076 Uiso 1 1 calc R . . H29C H 0.0614 0.2416 -0.1693 0.076 Uiso 1 1 calc R . . C30 C 0.16537(11) 0.27189(12) -0.0339(3) 0.0554(9) Uani 1 1 d . . . H30A H 0.1508 0.3002 -0.1049 0.083 Uiso 1 1 calc R . . H30B H 0.1867 0.2412 -0.0714 0.083 Uiso 1 1 calc R . . H30C H 0.1907 0.2918 0.0397 0.083 Uiso 1 1 calc R . . C31 C 0.08056(11) 0.29491(11) 0.0753(3) 0.0524(9) Uani 1 1 d . . . H31A H 0.0480 0.2787 0.1104 0.079 Uiso 1 1 calc R . . H31B H 0.0668 0.3221 0.0015 0.079 Uiso 1 1 calc R . . H31C H 0.1057 0.3157 0.1479 0.079 Uiso 1 1 calc R . . C41 C 0.06438(14) 0.0000 0.4051(3) 0.0329(10) Uani 1 2 d S . . C44 C -0.03961(14) 0.0000 0.2116(3) 0.0399(11) Uani 1 2 d S . . C45 C -0.01166(10) 0.05278(11) 0.2630(2) 0.0398(7) Uani 1 1 d . . . H45 H -0.0288 0.0889 0.2319 0.048 Uiso 1 1 calc R . . C46 C 0.03959(10) 0.05430(10) 0.3569(2) 0.0348(7) Uani 1 1 d . . . C47 C -0.09566(16) 0.0000 0.1068(4) 0.0569(13) Uani 1 2 d S . . C51 C -0.1407(2) -0.0520(2) 0.1632(5) 0.0499(17) Uani 0.50 1 d P A -1 H51A H -0.1771 -0.0535 0.1001 0.075 Uiso 0.50 1 calc PR A -1 H51B H -0.1475 -0.0409 0.2531 0.075 Uiso 0.50 1 calc PR A -1 H51C H -0.1224 -0.0905 0.1679 0.075 Uiso 0.50 1 calc PR A -1 C53 C -0.0838(2) -0.0370(3) -0.0291(4) 0.0541(18) Uani 0.50 1 d P A -1 H53A H -0.1188 -0.0378 -0.0971 0.081 Uiso 0.50 1 calc PR A -1 H53B H -0.0722 -0.0770 -0.0028 0.081 Uiso 0.50 1 calc PR A -1 H53C H -0.0533 -0.0177 -0.0669 0.081 Uiso 0.50 1 calc PR A -1 C55 C 0.3117(3) 0.0566(2) -0.1929(6) 0.076(2) Uani 0.50 1 d P B -1 H55A H 0.3233 0.0517 -0.2810 0.113 Uiso 0.50 1 calc PR B -1 H55B H 0.3363 0.0857 -0.1398 0.113 Uiso 0.50 1 calc PR B -1 H55C H 0.2719 0.0698 -0.2061 0.113 Uiso 0.50 1 calc PR B -1 C52 C -0.1248(2) -0.0499(2) 0.0776(6) 0.0592(19) Uani 0.50 1 d P A -2 H52A H -0.1592 -0.0422 0.0106 0.089 Uiso 0.50 1 calc PR A -2 H52B H -0.1357 -0.0657 0.1600 0.089 Uiso 0.50 1 calc PR A -2 H52C H -0.1008 -0.0783 0.0410 0.089 Uiso 0.50 1 calc PR A -2 C54 C 0.2771(3) 0.0476(3) -0.2118(6) 0.069(2) Uani 0.50 1 d P B -2 H54A H 0.2867 0.0486 -0.3026 0.103 Uiso 0.50 1 calc PR B -2 H54B H 0.2834 0.0863 -0.1702 0.103 Uiso 0.50 1 calc PR B -2 H54C H 0.2369 0.0366 -0.2182 0.103 Uiso 0.50 1 calc PR B -2 C56 C 0.3781(2) 0.0288(2) -0.1054(5) 0.068(2) Uani 0.50 1 d P B -2 H56A H 0.3901 0.0296 -0.1937 0.103 Uiso 0.50 1 calc PR B -2 H56B H 0.4055 0.0060 -0.0417 0.103 Uiso 0.50 1 calc PR B -2 H56C H 0.3765 0.0689 -0.0716 0.103 Uiso 0.50 1 calc PR B -2 C101 C 0.07950(13) 0.47042(18) 0.5631(3) 0.1060(19) Uani 1 1 d . . . C102 C 0.05764(15) 0.4402(2) 0.6595(4) 0.1084(15) Uani 1 1 d . . . C103 C 0.03410(14) 0.46973(17) 0.7562(3) 0.1024(18) Uani 1 1 d . . . F101 F 0.10182(9) 0.44059(14) 0.4647(2) 0.1499(11) Uani 1 1 d . . . F102 F 0.05774(13) 0.38064(14) 0.6615(3) 0.1675(13) Uani 1 1 d . . . F103 F 0.01165(10) 0.44015(13) 0.8522(2) 0.1401(10) Uani 1 1 d . . . F201 F 0.3372(2) 0.17661(17) 0.6225(4) 0.1484(10) Uani 0.50 1 d PDU C -1 F202 F 0.2330(2) 0.18145(17) 0.6962(4) 0.1403(13) Uani 0.50 1 d PDU C -1 F203 F 0.1516(2) 0.2573(2) 0.5596(5) 0.1496(12) Uani 0.50 1 d PDU C -1 F204 F 0.1795(2) 0.32780(19) 0.3597(5) 0.1484(10) Uani 0.50 1 d PDU C -1 F205 F 0.2835(3) 0.32174(18) 0.2829(4) 0.1403(13) Uani 0.50 1 d PDU C -1 F206 F 0.3639(2) 0.2457(2) 0.4189(5) 0.1496(12) Uani 0.50 1 d PDU C -1 C201 C 0.2984(2) 0.2132(2) 0.5565(5) 0.0811(14) Uani 0.50 1 d PDU C -1 C202 C 0.2444(2) 0.21717(19) 0.5910(5) 0.0988(19) Uani 0.50 1 d PDU C -1 C203 C 0.2046(3) 0.2540(2) 0.5279(5) 0.0879(16) Uani 0.50 1 d PDU C -1 C204 C 0.2178(2) 0.2898(3) 0.4212(5) 0.0811(14) Uani 0.50 1 d PDU C -1 C205 C 0.2719(2) 0.2868(2) 0.3880(6) 0.0988(19) Uani 0.50 1 d PDU C -1 C206 C 0.3115(3) 0.2506(2) 0.4533(6) 0.0879(16) Uani 0.50 1 d PDU C -1 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 O3 0.0369(13) 0.0529(15) 0.0296(12) 0.000 0.0018(10) 0.000 O1 0.0499(14) 0.0373(13) 0.0272(12) 0.000 0.0013(11) 0.000 O2 0.0507(9) 0.0381(9) 0.0294(8) 0.0007(8) 0.0024(7) 0.0017(8) C1 0.0271(17) 0.0208(17) 0.0317(18) 0.000 0.0008(15) 0.000 C2 0.0294(12) 0.0183(12) 0.0358(12) -0.0013(11) 0.0006(10) -0.0008(10) C3 0.0338(13) 0.0217(12) 0.0332(12) 0.0079(11) 0.0059(10) -0.0010(11) C4 0.0385(19) 0.0194(18) 0.0334(18) 0.000 0.0067(15) 0.000 C7 0.057(2) 0.0246(19) 0.0359(19) 0.000 0.0132(17) 0.000 C8 0.0384(13) 0.0230(13) 0.0350(13) -0.0051(11) 0.0081(11) -0.0040(11) C21 0.0393(13) 0.0206(12) 0.0310(13) -0.0083(11) -0.0006(11) -0.0033(11) C22 0.0362(13) 0.0299(13) 0.0323(12) -0.0099(11) 0.0069(11) -0.0019(11) C23 0.0329(13) 0.0342(14) 0.0401(13) -0.0033(12) 0.0085(11) 0.0024(11) C24 0.0353(13) 0.0230(13) 0.0397(13) -0.0073(11) 0.0056(11) 0.0023(11) C25 0.0459(14) 0.0161(12) 0.0340(12) -0.0055(10) 0.0117(11) -0.0073(11) C26 0.0364(13) 0.0171(12) 0.0317(12) -0.0075(11) 0.0072(11) -0.0052(11) C27 0.0368(14) 0.0305(14) 0.0436(14) 0.0066(12) 0.0048(12) -0.0036(11) C28 0.0422(14) 0.0350(15) 0.0380(14) -0.0010(12) 0.0103(12) 0.0024(12) C29 0.0580(17) 0.0397(16) 0.0518(16) 0.0053(14) 0.0023(14) -0.0013(14) C30 0.0516(16) 0.0441(16) 0.0685(17) 0.0249(14) 0.0056(14) -0.0049(14) C31 0.0589(17) 0.0314(15) 0.0637(17) 0.0032(14) 0.0021(14) 0.0066(14) C41 0.0391(19) 0.042(2) 0.0199(16) 0.000 0.0112(15) 0.000 C44 0.0355(19) 0.055(2) 0.0311(18) 0.000 0.0108(16) 0.000 C45 0.0399(14) 0.0455(15) 0.0358(13) 0.0077(12) 0.0116(11) 0.0058(12) C46 0.0401(13) 0.0355(14) 0.0313(12) -0.0016(12) 0.0127(11) 0.0016(12) C47 0.046(2) 0.090(3) 0.035(2) 0.000 0.0079(18) 0.000 C51 0.045(3) 0.052(3) 0.055(3) 0.001(3) 0.017(3) -0.009(3) C53 0.044(3) 0.089(4) 0.032(3) -0.008(3) 0.013(2) -0.008(3) C55 0.123(5) 0.044(4) 0.062(4) -0.005(3) 0.025(4) 0.006(4) C52 0.051(3) 0.038(3) 0.078(4) 0.009(3) -0.018(3) 0.005(3) C54 0.096(5) 0.074(4) 0.039(3) 0.022(3) 0.019(3) 0.010(4) C56 0.060(3) 0.105(5) 0.048(3) -0.003(3) 0.030(3) -0.020(3) C101 0.0493(18) 0.198(5) 0.0704(19) -0.016(2) 0.0113(16) 0.013(2) C102 0.067(2) 0.174(4) 0.082(2) 0.018(3) 0.0072(19) 0.012(3) C103 0.068(2) 0.186(5) 0.0553(18) 0.011(2) 0.0180(16) 0.002(2) F101 0.0932(14) 0.245(3) 0.1141(16) -0.0227(18) 0.0261(13) 0.0339(17) F102 0.174(2) 0.161(2) 0.164(2) 0.006(2) 0.020(2) 0.034(2) F103 0.1243(17) 0.209(3) 0.0909(14) 0.0280(16) 0.0295(13) -0.0046(17) F201 0.232(2) 0.0724(13) 0.1018(14) -0.0292(12) -0.0774(15) 0.0618(15) F202 0.286(4) 0.0577(13) 0.0815(15) -0.0133(12) 0.0438(19) -0.0050(18) F203 0.157(3) 0.1312(18) 0.156(2) -0.0867(16) 0.015(2) -0.0002(18) F204 0.232(2) 0.0724(13) 0.1018(14) -0.0292(12) -0.0774(15) 0.0618(15) F205 0.286(4) 0.0577(13) 0.0815(15) -0.0133(12) 0.0438(19) -0.0050(18) F206 0.157(3) 0.1312(18) 0.156(2) -0.0867(16) 0.015(2) -0.0002(18) C201 0.133(3) 0.0427(18) 0.053(2) -0.0200(17) -0.023(2) 0.040(2) C202 0.226(5) 0.0220(18) 0.0374(19) -0.0035(16) -0.005(3) 0.008(3) C203 0.125(4) 0.041(2) 0.084(3) -0.027(2) -0.019(3) 0.012(2) C204 0.133(3) 0.0427(18) 0.053(2) -0.0200(17) -0.023(2) 0.040(2) C205 0.226(5) 0.0220(18) 0.0374(19) -0.0035(16) -0.005(3) 0.008(3) C206 0.125(4) 0.041(2) 0.084(3) -0.027(2) -0.019(3) 0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O3 C41 1.401(3) . ? O1 C1 1.390(4) . ? O2 C21 1.398(3) . ? C1 C2 1.396(3) . ? C1 C2 1.396(3) 6 ? C2 C3 1.382(3) . ? C2 C8 1.527(3) . ? C3 C4 1.393(3) . ? C4 C3 1.393(3) 6 ? C4 C7 1.522(5) . ? C7 C55 1.452(6) . ? C7 C55 1.452(6) 6 ? C7 C56 1.544(6) . ? C7 C56 1.544(6) 6 ? C7 C54 1.591(6) 6 ? C7 C54 1.591(6) . ? C8 C26 1.516(3) . ? C21 C22 1.386(3) . ? C21 C26 1.402(3) . ? C22 C23 1.381(3) . ? C22 C28 1.531(3) . ? C23 C24 1.379(3) . ? C24 C25 1.389(3) . ? C24 C27 1.539(3) . ? C25 C26 1.393(3) . ? C27 C30 1.523(4) . ? C27 C29 1.529(3) . ? C27 C31 1.534(4) . ? C28 C46 1.529(3) . ? C41 C46 1.394(3) 6 ? C41 C46 1.394(3) . ? C44 C45 1.401(3) . ? C44 C45 1.401(3) 6 ? C44 C47 1.515(5) . ? C45 C46 1.375(3) . ? C47 C52 1.314(6) 6 ? C47 C52 1.314(6) . ? C47 C53 1.639(6) . ? C47 C53 1.639(6) 6 ? C47 C51 1.725(6) 6 ? C47 C51 1.725(6) . ? C101 C101 1.326(8) 6_565 ? C101 C102 1.339(5) . ? C101 F101 1.354(4) . ? C102 F102 1.335(5) . ? C102 C103 1.353(5) . ? C103 F103 1.335(4) . ? C103 C103 1.357(8) 6_565 ? F201 C201 1.305(6) . ? F202 C202 1.372(6) . ? F203 C203 1.330(8) . ? F204 C204 1.303(7) . ? F205 C205 1.363(7) . ? F206 C206 1.329(8) . ? C201 C202 1.365(7) . ? C201 C206 1.392(7) . ? C202 C203 1.313(6) . ? C203 C204 1.398(7) . ? C204 C205 1.359(7) . ? C205 C206 1.310(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 119.50(14) . . ? O1 C1 C2 119.50(14) . 6 ? C2 C1 C2 121.0(3) . 6 ? C3 C2 C1 118.0(2) . . ? C3 C2 C8 120.87(19) . . ? C1 C2 C8 121.2(2) . . ? C2 C3 C4 123.7(2) . . ? C3 C4 C3 115.6(3) . 6 ? C3 C4 C7 122.17(14) . . ? C3 C4 C7 122.17(14) 6 . ? C55 C7 C55 121.7(5) . 6 ? C55 C7 C4 116.2(3) . . ? C55 C7 C4 116.2(3) 6 . ? C55 C7 C56 71.2(3) . . ? C55 C7 C56 114.2(4) 6 . ? C4 C7 C56 107.2(3) . . ? C55 C7 C56 114.2(4) . 6 ? C55 C7 C56 71.2(3) 6 6 ? C4 C7 C56 107.2(3) . 6 ? C56 C7 C56 49.5(4) . 6 ? C55 C7 C54 108.3(4) . 6 ? C55 C7 C54 30.9(3) 6 6 ? C4 C7 C54 107.7(3) . 6 ? C56 C7 C54 140.5(4) . 6 ? C56 C7 C54 102.1(3) 6 6 ? C55 C7 C54 30.9(3) . . ? C55 C7 C54 108.3(4) 6 . ? C4 C7 C54 107.7(3) . . ? C56 C7 C54 102.1(3) . . ? C56 C7 C54 140.5(4) 6 . ? C54 C7 C54 84.3(5) 6 . ? C26 C8 C2 113.98(17) . . ? C22 C21 O2 119.8(2) . . ? C22 C21 C26 121.7(2) . . ? O2 C21 C26 118.37(19) . . ? C23 C22 C21 117.7(2) . . ? C23 C22 C28 120.3(2) . . ? C21 C22 C28 122.1(2) . . ? C24 C23 C22 123.5(2) . . ? C23 C24 C25 117.0(2) . . ? C23 C24 C27 120.8(2) . . ? C25 C24 C27 122.2(2) . . ? C24 C25 C26 122.6(2) . . ? C25 C26 C21 117.4(2) . . ? C25 C26 C8 121.0(2) . . ? C21 C26 C8 121.66(19) . . ? C30 C27 C29 107.7(2) . . ? C30 C27 C31 107.6(2) . . ? C29 C27 C31 109.58(19) . . ? C30 C27 C24 112.24(19) . . ? C29 C27 C24 109.13(19) . . ? C31 C27 C24 110.6(2) . . ? C46 C28 C22 114.42(19) . . ? C46 C41 C46 121.7(3) 6 . ? C46 C41 O3 119.17(14) 6 . ? C46 C41 O3 119.17(14) . . ? C45 C44 C45 115.2(3) . 6 ? C45 C44 C47 122.40(14) . . ? C45 C44 C47 122.40(14) 6 . ? C46 C45 C44 123.8(2) . . ? C45 C46 C41 117.7(2) . . ? C45 C46 C28 120.4(2) . . ? C41 C46 C28 121.9(2) . . ? C52 C47 C52 116.7(5) 6 . ? C52 C47 C44 119.9(3) 6 . ? C52 C47 C44 119.9(3) . . ? C52 C47 C53 114.1(4) 6 . ? C52 C47 C53 63.1(4) . . ? C44 C47 C53 107.8(3) . . ? C52 C47 C53 63.1(4) 6 6 ? C52 C47 C53 114.1(4) . 6 ? C44 C47 C53 107.8(3) . 6 ? C53 C47 C53 60.7(4) . 6 ? C52 C47 C51 34.4(3) 6 6 ? C52 C47 C51 109.0(4) . 6 ? C44 C47 C51 106.3(2) . 6 ? C53 C47 C51 143.7(3) . 6 ? C53 C47 C51 97.0(3) 6 6 ? C52 C47 C51 109.0(4) 6 . ? C52 C47 C51 34.4(3) . . ? C44 C47 C51 106.3(2) . . ? C53 C47 C51 97.0(3) . . ? C53 C47 C51 143.7(3) 6 . ? C51 C47 C51 85.0(4) 6 . ? C101 C101 C102 120.4(3) 6_565 . ? C101 C101 F101 119.6(2) 6_565 . ? C102 C101 F101 120.0(4) . . ? F102 C102 C101 121.1(4) . . ? F102 C102 C103 118.6(4) . . ? C101 C102 C103 120.3(4) . . ? F103 C103 C103 119.8(2) . 6_565 ? F103 C103 C102 121.0(4) . . ? C103 C103 C102 119.3(3) 6_565 . ? F201 C201 C202 120.3(5) . . ? F201 C201 C206 121.4(5) . . ? C202 C201 C206 118.3(5) . . ? C203 C202 C201 121.9(5) . . ? C203 C202 F202 120.6(5) . . ? C201 C202 F202 117.5(4) . . ? C202 C203 F203 122.1(5) . . ? C202 C203 C204 119.1(6) . . ? F203 C203 C204 118.8(5) . . ? F204 C204 C205 120.5(5) . . ? F204 C204 C203 120.1(5) . . ? C205 C204 C203 119.3(5) . . ? C206 C205 C204 121.0(6) . . ? C206 C205 F205 120.7(6) . . ? C204 C205 F205 118.2(5) . . ? C205 C206 F206 121.7(6) . . ? C205 C206 C201 120.4(6) . . ? F206 C206 C201 117.8(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 20.98 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.418 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.056 #===END data_sadf _database_code_depnum_ccdc_archive 'CCDC 237576' _audit_creation_method SHELXL-97 _chemical_name_systematic ; p-tert-butyl-calix[4]arene*2,3,5,6-tetrafluorobenzene ; _chemical_name_common p-tert-butyl-calix(4)arene*2,3,5,6-tetrafluorobenzene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H58 F4 O4' _chemical_formula_weight 798.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.9108(10) _cell_length_b 13.4629(10) _cell_length_c 14.8239(11) _cell_angle_alpha 67.4790(10) _cell_angle_beta 84.212(2) _cell_angle_gamma 67.9060(10) _cell_volume 2202.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9742 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD Bruker Smart 1000' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22346 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 26.37 _reflns_number_total 8993 _reflns_number_gt 5676 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0747P)^2^+0.2130P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8993 _refine_ls_number_parameters 763 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.0986 _refine_ls_R_factor_gt 0.0552 _refine_ls_wR_factor_ref 0.1480 _refine_ls_wR_factor_gt 0.1289 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.49599(6) -0.15295(6) 0.15954(5) 0.0322(2) Uani 1 1 d . . . O2 O 0.65068(6) -0.08517(6) 0.18953(5) 0.0346(2) Uani 1 1 d . . . O3 O 0.54237(6) 0.12249(6) 0.06457(5) 0.0320(2) Uani 1 1 d . . . O4 O 0.38859(6) 0.05663(6) 0.02834(5) 0.0300(2) Uani 1 1 d . . . C1 C 0.43447(8) -0.18526(8) 0.24042(7) 0.0261(3) Uani 1 1 d . . . C2 C 0.32035(8) -0.15779(8) 0.22626(7) 0.0257(3) Uani 1 1 d . . . C3 C 0.26254(9) -0.19807(8) 0.30745(8) 0.0294(3) Uani 1 1 d . . . C4 C 0.31317(9) -0.26315(8) 0.40103(8) 0.0306(3) Uani 1 1 d . . . C5 C 0.42635(9) -0.28555(9) 0.41162(8) 0.0322(3) Uani 1 1 d . . . C6 C 0.48934(8) -0.24699(8) 0.33246(8) 0.0282(3) Uani 1 1 d . . . C7 C 0.24344(10) -0.30970(10) 0.48528(9) 0.0404(4) Uani 1 1 d . . . C8 C 0.25930(8) -0.08341(8) 0.12661(8) 0.0272(3) Uani 1 1 d . A . C9 C 0.30955(12) -0.37395(13) 0.58321(10) 0.0601(5) Uani 1 1 d . . . C10 C 0.20499(11) -0.39477(11) 0.46341(10) 0.0551(4) Uani 1 1 d . . . C11 C 0.13875(11) -0.21087(13) 0.49289(10) 0.0570(5) Uani 1 1 d . . . C21 C 0.65363(8) -0.08707(9) 0.28351(8) 0.0290(3) Uani 1 1 d D A . C22 C 0.64035(8) -0.17963(9) 0.36236(8) 0.0310(3) Uani 1 1 d . . . C23 C 0.65754(9) -0.18673(9) 0.45588(8) 0.0343(3) Uani 1 1 d . A . C24 C 0.68605(9) -0.10518(9) 0.47399(8) 0.0344(3) Uani 1 1 d D . . C25 C 0.69305(9) -0.01205(9) 0.39228(8) 0.0326(3) Uani 1 1 d . A . C26 C 0.67563(8) -0.00009(9) 0.29675(8) 0.0304(3) Uani 1 1 d . . . C28 C 0.61305(9) -0.27348(9) 0.34720(8) 0.0326(3) Uani 1 1 d . . . C27A C 0.71201(12) -0.12511(13) 0.57981(11) 0.0389(4) Uani 0.7857(13) 1 d PD A 1 C29 C 0.75132(15) -0.03353(14) 0.58585(13) 0.0577(6) Uani 0.7857(13) 1 d PD A 1 H29A H 0.7658 -0.0491 0.6545 0.086 Uiso 0.7857(13) 1 calc PR A 1 H29B H 0.6931 0.0432 0.5562 0.086 Uiso 0.7857(13) 1 calc PR A 1 H29C H 0.8202 -0.0362 0.5507 0.086 Uiso 0.7857(13) 1 calc PR A 1 C30 C 0.80601(14) -0.24327(15) 0.62843(13) 0.0557(6) Uani 0.7857(13) 1 d PD A 1 H30A H 0.7840 -0.3044 0.6261 0.084 Uiso 0.7857(13) 1 calc PR A 1 H30B H 0.8191 -0.2562 0.6967 0.084 Uiso 0.7857(13) 1 calc PR A 1 H30C H 0.8748 -0.2444 0.5935 0.084 Uiso 0.7857(13) 1 calc PR A 1 C31 C 0.60735(14) -0.12246(17) 0.63860(12) 0.0604(6) Uani 0.7857(13) 1 d PD A 1 H31A H 0.5803 -0.1797 0.6346 0.091 Uiso 0.7857(13) 1 calc PR A 1 H31B H 0.5490 -0.0453 0.6118 0.091 Uiso 0.7857(13) 1 calc PR A 1 H31C H 0.6256 -0.1408 0.7071 0.091 Uiso 0.7857(13) 1 calc PR A 1 C27B C 0.7063(5) -0.1062(5) 0.5746(4) 0.0389(4) Uani 0.2143(13) 1 d PD A 2 C32 C 0.6289(5) 0.0052(4) 0.5884(5) 0.0616(19) Uiso 0.2143(13) 1 d PD A 2 H32A H 0.6467 0.0708 0.5421 0.092 Uiso 0.2143(13) 1 calc PR A 2 H32B H 0.6398 -0.0018 0.6553 0.092 Uiso 0.2143(13) 1 calc PR A 2 H32C H 0.5508 0.0178 0.5765 0.092 Uiso 0.2143(13) 1 calc PR A 2 C33 C 0.8285(4) -0.1203(5) 0.5824(5) 0.065(2) Uiso 0.2143(13) 1 d PD A 2 H33A H 0.8447 -0.0617 0.5252 0.097 Uiso 0.2143(13) 1 calc PR A 2 H33B H 0.8774 -0.1975 0.5851 0.097 Uiso 0.2143(13) 1 calc PR A 2 H33C H 0.8419 -0.1107 0.6419 0.097 Uiso 0.2143(13) 1 calc PR A 2 C34 C 0.6857(5) -0.2105(5) 0.6547(5) 0.067(2) Uiso 0.2143(13) 1 d PD A 2 H34A H 0.6111 -0.2078 0.6432 0.101 Uiso 0.2143(13) 1 calc PR A 2 H34B H 0.6907 -0.2072 0.7190 0.101 Uiso 0.2143(13) 1 calc PR A 2 H34C H 0.7423 -0.2825 0.6526 0.101 Uiso 0.2143(13) 1 calc PR A 2 C41 C 0.50648(8) 0.20800(8) 0.10308(7) 0.0269(3) Uani 1 1 d . A . C42 C 0.57576(9) 0.20478(9) 0.17087(8) 0.0306(3) Uani 1 1 d . . . C43 C 0.54205(9) 0.29870(9) 0.19990(8) 0.0358(3) Uani 1 1 d . A . C44 C 0.44241(10) 0.39288(9) 0.16521(8) 0.0370(3) Uani 1 1 d D . . C45 C 0.37351(9) 0.38887(9) 0.10172(8) 0.0339(3) Uani 1 1 d . A . C46 C 0.40267(8) 0.29719(8) 0.06985(7) 0.0280(3) Uani 1 1 d . . . C48 C 0.68623(9) 0.10343(9) 0.21073(8) 0.0330(3) Uani 1 1 d . A . C47A C 0.41852(13) 0.49612(11) 0.19626(11) 0.0411(4) Uani 0.8170(13) 1 d PD A 1 C49 C 0.31326(18) 0.59625(13) 0.14146(16) 0.0928(7) Uani 0.8170(13) 1 d PD A 1 H49A H 0.3228 0.6189 0.0709 0.139 Uiso 0.8170(13) 1 calc PR A 1 H49B H 0.3006 0.6621 0.1602 0.139 Uiso 0.8170(13) 1 calc PR A 1 H49C H 0.2488 0.5720 0.1581 0.139 Uiso 0.8170(13) 1 calc PR A 1 C50 C 0.51792(15) 0.53801(13) 0.17275(13) 0.0607(5) Uani 0.8170(13) 1 d PD A 1 H50A H 0.5862 0.4745 0.2074 0.091 Uiso 0.8170(13) 1 calc PR A 1 H50B H 0.5026 0.6027 0.1938 0.091 Uiso 0.8170(13) 1 calc PR A 1 H50C H 0.5280 0.5634 0.1022 0.091 Uiso 0.8170(13) 1 calc PR A 1 C51 C 0.40190(13) 0.46033(13) 0.30500(11) 0.0486(5) Uani 0.8170(13) 1 d PD A 1 H51A H 0.4687 0.3952 0.3407 0.073 Uiso 0.8170(13) 1 calc PR A 1 H51B H 0.3368 0.4371 0.3201 0.073 Uiso 0.8170(13) 1 calc PR A 1 H51C H 0.3894 0.5255 0.3246 0.073 Uiso 0.8170(13) 1 calc PR A 1 C47B C 0.3853(5) 0.5084(5) 0.1850(4) 0.0411(4) Uani 0.1830(13) 1 d PD A 2 C52 C 0.2610(4) 0.5379(6) 0.2126(5) 0.058(2) Uiso 0.1830(13) 1 d PD A 2 H52A H 0.2155 0.5468 0.1589 0.087 Uiso 0.1830(13) 1 calc PR A 2 H52B H 0.2342 0.6101 0.2243 0.087 Uiso 0.1830(13) 1 calc PR A 2 H52C H 0.2547 0.4752 0.2719 0.087 Uiso 0.1830(13) 1 calc PR A 2 C53 C 0.3968(6) 0.6078(5) 0.0971(5) 0.057(2) Uiso 0.1830(13) 1 d PD A 2 H53A H 0.3708 0.6068 0.0378 0.086 Uiso 0.1830(13) 1 calc PR A 2 H53B H 0.4755 0.6001 0.0921 0.086 Uiso 0.1830(13) 1 calc PR A 2 H53C H 0.3517 0.6810 0.1045 0.086 Uiso 0.1830(13) 1 calc PR A 2 C54 C 0.4527(6) 0.4922(6) 0.2733(4) 0.063(2) Uiso 0.1830(13) 1 d PD A 2 H54A H 0.4296 0.5658 0.2823 0.094 Uiso 0.1830(13) 1 calc PR A 2 H54B H 0.5328 0.4663 0.2613 0.094 Uiso 0.1830(13) 1 calc PR A 2 H54C H 0.4386 0.4342 0.3323 0.094 Uiso 0.1830(13) 1 calc PR A 2 C61 C 0.28650(8) 0.10983(8) 0.06182(7) 0.0253(3) Uani 1 1 d . A . C62 C 0.25234(8) 0.22603(8) 0.04815(7) 0.0263(3) Uani 1 1 d . . . C63 C 0.14752(9) 0.27742(8) 0.07949(8) 0.0308(3) Uani 1 1 d . A . C64 C 0.07660(9) 0.21755(9) 0.12298(8) 0.0308(3) Uani 1 1 d . . . C65 C 0.11597(8) 0.10073(9) 0.13604(8) 0.0300(3) Uani 1 1 d . A . C66 C 0.21977(8) 0.04518(8) 0.10695(7) 0.0259(3) Uani 1 1 d . . . C67 C -0.04242(9) 0.27616(9) 0.15094(9) 0.0388(4) Uani 1 1 d . A . C68 C 0.32533(9) 0.29672(8) -0.00045(8) 0.0287(3) Uani 1 1 d . A . C69 C -0.06374(11) 0.20372(11) 0.25396(10) 0.0512(4) Uani 1 1 d . . . C70 C -0.12702(12) 0.28303(16) 0.08009(12) 0.0713(6) Uani 1 1 d . . . C71 C -0.06256(13) 0.39526(12) 0.14919(15) 0.0777(6) Uani 1 1 d . . . C101 C 0.93612(12) 0.86031(13) 0.16104(11) 0.0505(5) Uani 0.8924(8) 1 d P B -3 C102 C 0.92337(16) 0.77974(15) 0.13685(13) 0.0700(6) Uani 0.8924(8) 1 d P B -3 C103 C 0.90902(15) 0.68764(13) 0.20931(15) 0.0788(6) Uani 0.8924(8) 1 d P B -3 C104 C 0.91286(14) 0.67586(14) 0.30632(16) 0.0707(7) Uani 0.8924(8) 1 d P B -3 C105 C 0.92711(11) 0.75818(13) 0.33067(11) 0.0477(5) Uani 0.8924(8) 1 d P B -3 C106 C 0.93886(10) 0.84992(11) 0.25461(11) 0.0427(4) Uani 0.8924(8) 1 d P B -3 F101 F 0.94804(9) 0.95564(10) 0.09072(8) 0.0914(5) Uani 0.8924(8) 1 d P B -3 F103 F 0.89207(14) 0.60530(10) 0.18960(13) 0.1622(6) Uani 0.8924(8) 1 d P B -3 F104 F 0.89806(11) 0.58402(10) 0.37800(13) 0.1358(7) Uani 0.8924(8) 1 d P B -3 F106 F 0.95143(7) 0.93499(7) 0.27457(8) 0.0689(3) Uani 0.8924(8) 1 d P B -3 H105 H 0.9328(12) 0.7497(12) 0.3946(11) 0.064(5) Uiso 0.8924(8) 1 d P B -3 H102 H 0.9333(17) 0.7800(16) 0.0750(15) 0.106(7) Uiso 0.8924(8) 1 d P B -3 H3 H 0.1833(9) -0.1777(9) 0.2984(8) 0.039(3) Uiso 1 1 d . . . H5 H 0.4682(8) -0.3317(8) 0.4771(7) 0.029(3) Uiso 1 1 d . . . H23 H 0.6509(9) -0.2547(9) 0.5135(9) 0.044(3) Uiso 1 1 d . . . H25 H 0.7127(9) 0.0497(9) 0.4012(8) 0.036(3) Uiso 1 1 d . . . H43 H 0.5889(9) 0.2983(9) 0.2456(8) 0.041(3) Uiso 1 1 d . . . H45 H 0.3014(9) 0.4508(9) 0.0788(8) 0.043(3) Uiso 1 1 d . . . H63 H 0.1250(8) 0.3580(8) 0.0700(7) 0.029(3) Uiso 1 1 d . . . H8A H 0.1924(9) -0.1026(9) 0.1250(8) 0.033(3) Uiso 1 1 d . . . H28A H 0.6548(8) -0.2923(8) 0.2902(8) 0.030(3) Uiso 1 1 d . . . H48A H 0.7272(9) 0.0768(9) 0.1576(8) 0.032(3) Uiso 1 1 d . . . H68A H 0.2751(8) 0.3771(8) -0.0358(7) 0.027(3) Uiso 1 1 d . . . H8B H 0.3108(8) -0.1016(8) 0.0757(7) 0.024(3) Uiso 1 1 d . . . H28B H 0.6387(9) -0.3412(9) 0.4066(8) 0.036(3) Uiso 1 1 d . . . H48B H 0.7324(9) 0.1341(9) 0.2330(8) 0.034(3) Uiso 1 1 d . . . H68B H 0.3692(8) 0.2703(8) -0.0515(8) 0.029(3) Uiso 1 1 d . . . H65 H 0.0659(9) 0.0580(9) 0.1633(8) 0.032(3) Uiso 1 1 d . . . H9A H 0.3201(10) -0.2995(10) 0.5946(9) 0.051(4) Uiso 1 1 d . . . H10B H 0.1568(11) -0.3513(11) 0.3954(10) 0.069(4) Uiso 1 1 d . . . H11A H 0.0925(11) -0.1675(11) 0.4293(10) 0.068(4) Uiso 1 1 d . . . H11B H 0.1673(12) -0.1559(12) 0.5175(11) 0.078(5) Uiso 1 1 d . . . H69A H -0.1450(10) 0.2449(10) 0.2693(9) 0.050(4) Uiso 1 1 d . . . H11C H 0.0894(12) -0.2418(11) 0.5452(10) 0.071(5) Uiso 1 1 d . . . H9B H 0.3679(11) -0.4492(12) 0.5751(10) 0.071(5) Uiso 1 1 d . . . H9C H 0.2586(12) -0.4035(12) 0.6390(11) 0.072(5) Uiso 1 1 d . . . H71A H -0.1407(13) 0.4258(12) 0.1753(11) 0.083(5) Uiso 1 1 d . . . H69B H -0.0009(14) 0.1938(14) 0.3066(12) 0.099(6) Uiso 1 1 d . . . H10A H 0.2761(12) -0.4651(12) 0.4608(11) 0.078(5) Uiso 1 1 d . . . H70A H -0.1074(12) 0.3442(12) 0.0180(11) 0.082(5) Uiso 1 1 d . . . H10C H 0.1563(12) -0.4280(12) 0.5190(11) 0.078(5) Uiso 1 1 d . . . H70B H -0.1144(14) 0.1997(14) 0.0784(12) 0.098(6) Uiso 1 1 d . . . H70C H -0.2124(13) 0.3226(12) 0.0955(11) 0.079(5) Uiso 1 1 d . . . H71B H -0.0606(15) 0.4470(15) 0.0748(14) 0.115(7) Uiso 1 1 d . . . H69C H -0.0582(13) 0.1283(13) 0.2576(11) 0.083(5) Uiso 1 1 d . . . H71C H -0.0052(13) 0.3840(13) 0.2008(12) 0.085(5) Uiso 1 1 d . . . H01 H 0.601(2) -0.1046(19) 0.1811(18) 0.054(3) Uiso 0.539(9) 1 d P C 1 H02 H 0.5915(19) 0.0632(19) 0.0987(17) 0.054(3) Uiso 0.539(9) 1 d P C 1 H03 H 0.429(2) 0.085(2) 0.0319(18) 0.054(3) Uiso 0.539(9) 1 d P C 1 H04 H 0.4587(19) -0.1049(19) 0.1089(17) 0.054(3) Uiso 0.539(9) 1 d P C 1 H05 H 0.490(2) 0.107(2) 0.042(2) 0.054(3) Uiso 0.461(9) 1 d P C 2 H06 H 0.553(2) -0.143(2) 0.172(2) 0.054(3) Uiso 0.461(9) 1 d P C 2 H07 H 0.431(2) -0.017(2) 0.072(2) 0.054(3) Uiso 0.461(9) 1 d P C 2 H08 H 0.614(2) -0.023(2) 0.149(2) 0.054(3) Uiso 0.461(9) 1 d P C 2 F203 F 0.9024(8) 0.5410(6) 0.2830(8) 0.109(3) Uani 0.1076(8) 1 d PU B -4 F204 F 0.9053(7) 0.5909(8) 0.4510(7) 0.080(3) Uani 0.1076(8) 1 d PU B -4 F201 F 0.9662(9) 0.8712(9) 0.0835(7) 0.131(4) Uani 0.1076(8) 1 d PU B -4 F206 F 0.9398(6) 0.9399(6) 0.2117(5) 0.136(5) Uani 0.1076(8) 1 d PU B -4 C201 C 0.9739(6) 0.7923(6) 0.1833(5) 0.083(2) Uiso 0.1076(8) 1 d PR B -4 C202 C 0.9710(6) 0.6856(6) 0.1958(5) 0.083(2) Uiso 0.1076(8) 1 d PR B -4 H202 H 0.9899 0.6579 0.1439 0.100 Uiso 0.1076(8) 1 calc PR B -4 C203 C 0.9405(6) 0.6195(6) 0.2842(5) 0.083(2) Uiso 0.1076(8) 1 d PR B -4 C204 C 0.9128(6) 0.6599(6) 0.3601(5) 0.083(2) Uiso 0.1076(8) 1 d PR B -4 C205 C 0.9157(6) 0.7666(6) 0.3476(5) 0.083(2) Uiso 0.1076(8) 1 d PR B -4 H205 H 0.8969 0.7943 0.3994 0.100 Uiso 0.1076(8) 1 calc PR B -4 C206 C 0.9463(6) 0.8327(6) 0.2591(5) 0.083(2) Uiso 0.1076(8) 1 d PR B -4 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0350(3) 0.0327(3) 0.0292(4) -0.0095(3) 0.0077(3) -0.0164(3) O2 0.0358(4) 0.0347(3) 0.0331(4) -0.0099(3) 0.0022(3) -0.0155(3) O3 0.0369(4) 0.0271(3) 0.0327(4) -0.0114(3) 0.0034(3) -0.0127(3) O4 0.0333(3) 0.0254(3) 0.0320(4) -0.0112(3) 0.0080(3) -0.0127(3) C1 0.0334(5) 0.0194(4) 0.0275(5) -0.0088(4) 0.0062(4) -0.0129(4) C2 0.0332(5) 0.0174(4) 0.0276(5) -0.0086(3) 0.0027(4) -0.0106(4) C3 0.0314(5) 0.0226(4) 0.0334(5) -0.0085(4) 0.0039(4) -0.0115(4) C4 0.0372(5) 0.0251(4) 0.0290(5) -0.0074(4) 0.0050(4) -0.0144(4) C5 0.0412(5) 0.0266(5) 0.0271(5) -0.0057(4) 0.0000(4) -0.0146(4) C6 0.0335(5) 0.0195(4) 0.0305(5) -0.0057(4) -0.0004(4) -0.0118(4) C7 0.0455(6) 0.0403(6) 0.0308(6) -0.0059(5) 0.0091(5) -0.0201(5) C8 0.0312(5) 0.0248(4) 0.0271(5) -0.0084(4) 0.0024(4) -0.0134(4) C9 0.0627(7) 0.0770(8) 0.0330(7) -0.0040(6) 0.0057(6) -0.0354(6) C10 0.0644(7) 0.0538(7) 0.0478(8) -0.0058(6) 0.0110(6) -0.0379(5) C11 0.0501(7) 0.0700(8) 0.0446(7) -0.0173(6) 0.0172(6) -0.0234(6) C21 0.0241(4) 0.0289(5) 0.0309(5) -0.0082(4) 0.0005(4) -0.0092(4) C22 0.0256(5) 0.0268(5) 0.0361(6) -0.0056(4) 0.0002(4) -0.0109(4) C23 0.0309(5) 0.0334(5) 0.0328(6) -0.0020(4) -0.0010(4) -0.0156(4) C24 0.0316(5) 0.0357(5) 0.0342(6) -0.0081(4) 0.0023(4) -0.0159(4) C25 0.0288(5) 0.0319(5) 0.0381(6) -0.0106(4) -0.0002(4) -0.0143(4) C26 0.0248(4) 0.0290(5) 0.0358(6) -0.0080(4) 0.0006(4) -0.0122(4) C28 0.0325(5) 0.0252(5) 0.0339(6) -0.0034(4) -0.0012(5) -0.0113(4) C27A 0.0415(6) 0.0391(6) 0.0360(6) -0.0104(5) -0.0027(5) -0.0172(5) C29 0.0836(10) 0.0569(8) 0.0405(9) -0.0144(7) -0.0051(8) -0.0361(8) C30 0.0558(9) 0.0559(9) 0.0477(9) -0.0131(7) -0.0177(8) -0.0137(8) C31 0.0497(9) 0.0912(12) 0.0356(8) -0.0207(8) 0.0063(7) -0.0251(8) C27B 0.0415(6) 0.0391(6) 0.0360(6) -0.0104(5) -0.0027(5) -0.0172(5) C41 0.0357(5) 0.0231(4) 0.0246(5) -0.0066(4) 0.0089(4) -0.0179(4) C42 0.0392(5) 0.0284(4) 0.0260(5) -0.0043(4) 0.0048(4) -0.0209(4) C43 0.0526(6) 0.0320(5) 0.0270(5) -0.0051(4) -0.0025(5) -0.0251(4) C44 0.0585(6) 0.0275(5) 0.0268(5) -0.0066(4) -0.0001(5) -0.0208(4) C45 0.0446(6) 0.0236(5) 0.0294(5) -0.0042(4) 0.0029(5) -0.0143(4) C46 0.0374(5) 0.0242(4) 0.0235(5) -0.0050(4) 0.0064(4) -0.0175(4) C48 0.0346(5) 0.0326(5) 0.0341(6) -0.0072(4) -0.0001(4) -0.0199(4) C47A 0.0594(8) 0.0276(5) 0.0373(6) -0.0117(5) -0.0119(6) -0.0139(5) C49 0.1179(15) 0.0305(7) 0.1215(12) -0.0430(7) -0.0676(11) 0.0151(9) C50 0.1081(11) 0.0465(7) 0.0501(9) -0.0216(6) 0.0180(8) -0.0521(7) C51 0.0553(8) 0.0491(7) 0.0542(8) -0.0313(6) 0.0134(7) -0.0231(6) C47B 0.0594(8) 0.0276(5) 0.0373(6) -0.0117(5) -0.0119(6) -0.0139(5) C61 0.0294(5) 0.0251(4) 0.0221(5) -0.0092(4) 0.0001(4) -0.0099(4) C62 0.0328(5) 0.0233(4) 0.0227(5) -0.0057(4) -0.0009(4) -0.0124(4) C63 0.0364(5) 0.0199(4) 0.0322(5) -0.0064(4) -0.0013(4) -0.0088(4) C64 0.0294(5) 0.0273(5) 0.0309(5) -0.0072(4) -0.0006(4) -0.0085(4) C65 0.0300(5) 0.0277(5) 0.0293(5) -0.0046(4) 0.0005(4) -0.0136(4) C66 0.0314(5) 0.0231(4) 0.0225(5) -0.0058(4) -0.0004(4) -0.0116(4) C67 0.0312(5) 0.0309(5) 0.0454(6) -0.0106(5) 0.0048(5) -0.0064(4) C68 0.0345(5) 0.0211(4) 0.0267(5) -0.0050(4) 0.0019(4) -0.0103(4) C69 0.0458(7) 0.0485(6) 0.0539(7) -0.0225(5) 0.0184(6) -0.0123(5) C70 0.0349(7) 0.1017(11) 0.0587(9) -0.0253(8) -0.0036(6) -0.0086(7) C71 0.0512(8) 0.0429(7) 0.1280(13) -0.0347(8) 0.0331(8) -0.0101(6) C101 0.0428(7) 0.0463(8) 0.0491(8) -0.0064(7) -0.0031(6) -0.0127(6) C102 0.0675(10) 0.0666(9) 0.0671(10) -0.0303(8) -0.0124(8) -0.0062(8) C103 0.0684(10) 0.0573(7) 0.1266(12) -0.0549(7) -0.0264(9) -0.0111(7) C104 0.0589(9) 0.0364(8) 0.0958(14) 0.0044(8) -0.0061(9) -0.0225(6) C105 0.0352(6) 0.0546(8) 0.0481(8) -0.0109(6) 0.0017(6) -0.0195(6) C106 0.0284(6) 0.0425(6) 0.0557(8) -0.0150(6) 0.0003(6) -0.0146(5) F101 0.0931(6) 0.0854(7) 0.0665(7) 0.0125(6) 0.0018(6) -0.0432(5) F103 0.1980(12) 0.0866(6) 0.2345(13) -0.0837(7) -0.0639(10) -0.0438(7) F104 0.1326(8) 0.0687(6) 0.1620(14) 0.0353(8) -0.0231(9) -0.0631(6) F106 0.0602(4) 0.0607(4) 0.1031(7) -0.0386(4) 0.0000(5) -0.0314(3) F203 0.129(6) 0.093(3) 0.183(6) -0.111(3) 0.064(5) -0.077(3) F204 0.065(5) 0.070(5) 0.075(6) 0.005(5) -0.007(4) -0.025(4) F201 0.232(7) 0.170(6) 0.058(6) -0.022(5) 0.028(6) -0.170(5) F206 0.156(8) 0.093(6) 0.182(12) -0.052(7) 0.064(8) -0.084(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3878(12) . ? O2 C21 1.3876(14) . ? O3 C41 1.3838(14) . ? O4 C61 1.3881(12) . ? C1 C6 1.3920(14) . ? C1 C2 1.3945(15) . ? C2 C3 1.3867(15) . ? C2 C8 1.5212(14) . ? C3 C4 1.3931(14) . ? C4 C5 1.3889(16) . ? C4 C7 1.5366(16) . ? C5 C6 1.4022(15) . ? C6 C28 1.5192(16) . ? C7 C9 1.5220(18) . ? C7 C11 1.5301(18) . ? C7 C10 1.552(2) . ? C8 C66 1.5236(14) . ? C21 C26 1.3885(18) . ? C21 C22 1.3975(14) . ? C22 C23 1.3874(18) . ? C22 C28 1.5296(18) . ? C23 C24 1.4009(19) . ? C24 C25 1.3954(15) . ? C24 C27B 1.534(6) . ? C24 C27A 1.537(2) . ? C25 C26 1.3944(17) . ? C26 C48 1.5277(15) . ? C27A C31 1.529(2) . ? C27A C29 1.533(3) . ? C27A C30 1.5391(19) . ? C27B C33 1.529(8) . ? C27B C32 1.535(7) . ? C27B C34 1.546(8) . ? C41 C42 1.3894(17) . ? C41 C46 1.3965(13) . ? C42 C43 1.3922(17) . ? C42 C48 1.5277(13) . ? C43 C44 1.3907(14) . ? C44 C45 1.3870(19) . ? C44 C47A 1.542(2) . ? C44 C47B 1.579(6) . ? C45 C46 1.3963(17) . ? C46 C68 1.5174(17) . ? C47A C51 1.513(2) . ? C47A C49 1.526(2) . ? C47A C50 1.546(3) . ? C47B C53 1.512(8) . ? C47B C54 1.545(9) . ? C47B C52 1.553(8) . ? C61 C62 1.3926(15) . ? C61 C66 1.3961(15) . ? C62 C63 1.3931(14) . ? C62 C68 1.5249(16) . ? C63 C64 1.3934(16) . ? C64 C65 1.3981(16) . ? C64 C67 1.5382(15) . ? C65 C66 1.3849(14) . ? C67 C71 1.515(2) . ? C67 C69 1.5282(17) . ? C67 C70 1.545(2) . ? C101 C102 1.333(3) . ? C101 C106 1.342(2) . ? C101 F101 1.3598(18) . ? C102 C103 1.356(3) . ? C103 F103 1.344(3) . ? C103 C104 1.389(3) . ? C104 F104 1.351(2) . ? C104 C105 1.366(3) . ? C105 C106 1.3636(19) . ? C106 F106 1.354(2) . ? F203 C203 1.328(13) . ? F204 C204 1.331(11) . ? F201 C201 1.439(12) . ? F206 C206 1.3144 . ? C201 C202 1.3900 . ? C201 C206 1.3900 . ? C202 C203 1.3900 . ? C203 C204 1.3900 . ? C204 C205 1.3900 . ? C205 C206 1.3900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C6 118.93(9) . . ? O1 C1 C2 118.78(9) . . ? C6 C1 C2 122.26(9) . . ? C3 C2 C1 117.55(9) . . ? C3 C2 C8 120.44(9) . . ? C1 C2 C8 121.98(9) . . ? C2 C3 C4 123.01(10) . . ? C5 C4 C3 117.16(10) . . ? C5 C4 C7 123.73(9) . . ? C3 C4 C7 119.07(10) . . ? C4 C5 C6 122.54(10) . . ? C1 C6 C5 117.43(10) . . ? C1 C6 C28 121.69(9) . . ? C5 C6 C28 120.87(9) . . ? C9 C7 C11 109.04(12) . . ? C9 C7 C4 112.41(11) . . ? C11 C7 C4 110.44(9) . . ? C9 C7 C10 108.25(11) . . ? C11 C7 C10 107.95(11) . . ? C4 C7 C10 108.62(11) . . ? C2 C8 C66 112.02(10) . . ? O2 C21 C26 118.93(9) . . ? O2 C21 C22 119.04(11) . . ? C26 C21 C22 121.94(11) . . ? C23 C22 C21 117.70(12) . . ? C23 C22 C28 120.55(9) . . ? C21 C22 C28 121.69(11) . . ? C22 C23 C24 122.98(10) . . ? C25 C24 C23 116.51(11) . . ? C25 C24 C27B 117.1(2) . . ? C23 C24 C27B 126.4(2) . . ? C25 C24 C27A 124.22(13) . . ? C23 C24 C27A 119.21(11) . . ? C27B C24 C27A 8.2(2) . . ? C26 C25 C24 122.87(12) . . ? C21 C26 C25 117.81(10) . . ? C21 C26 C48 122.14(11) . . ? C25 C26 C48 119.99(11) . . ? C6 C28 C22 115.27(9) . . ? C31 C27A C29 108.37(16) . . ? C31 C27A C24 109.73(13) . . ? C29 C27A C24 112.44(12) . . ? C31 C27A C30 108.75(13) . . ? C29 C27A C30 106.95(14) . . ? C24 C27A C30 110.48(14) . . ? C33 C27B C24 107.2(4) . . ? C33 C27B C32 110.0(6) . . ? C24 C27B C32 112.1(4) . . ? C33 C27B C34 109.6(4) . . ? C24 C27B C34 108.9(5) . . ? C32 C27B C34 109.0(5) . . ? O3 C41 C42 119.35(8) . . ? O3 C41 C46 118.56(10) . . ? C42 C41 C46 122.06(11) . . ? C41 C42 C43 117.56(9) . . ? C41 C42 C48 121.50(11) . . ? C43 C42 C48 120.92(11) . . ? C44 C43 C42 122.81(12) . . ? C45 C44 C43 117.26(11) . . ? C45 C44 C47A 124.62(10) . . ? C43 C44 C47A 118.06(12) . . ? C45 C44 C47B 109.5(3) . . ? C43 C44 C47B 133.2(3) . . ? C47A C44 C47B 15.5(3) . . ? C44 C45 C46 122.59(9) . . ? C45 C46 C41 117.52(11) . . ? C45 C46 C68 120.92(9) . . ? C41 C46 C68 121.54(10) . . ? C42 C48 C26 114.72(9) . . ? C51 C47A C49 108.97(14) . . ? C51 C47A C44 109.93(11) . . ? C49 C47A C44 110.38(14) . . ? C51 C47A C50 108.91(14) . . ? C49 C47A C50 108.55(13) . . ? C44 C47A C50 110.06(12) . . ? C53 C47B C54 108.9(6) . . ? C53 C47B C52 109.9(5) . . ? C54 C47B C52 106.9(5) . . ? C53 C47B C44 109.1(5) . . ? C54 C47B C44 105.6(4) . . ? C52 C47B C44 116.1(6) . . ? O4 C61 C62 119.56(9) . . ? O4 C61 C66 118.66(9) . . ? C62 C61 C66 121.77(9) . . ? C61 C62 C63 117.83(10) . . ? C61 C62 C68 121.93(9) . . ? C63 C62 C68 120.24(9) . . ? C62 C63 C64 122.73(10) . . ? C63 C64 C65 116.91(10) . . ? C63 C64 C67 122.80(10) . . ? C65 C64 C67 120.20(10) . . ? C66 C65 C64 122.72(10) . . ? C65 C66 C61 118.03(9) . . ? C65 C66 C8 120.05(10) . . ? C61 C66 C8 121.91(9) . . ? C71 C67 C69 107.45(13) . . ? C71 C67 C64 112.45(11) . . ? C69 C67 C64 110.60(8) . . ? C71 C67 C70 110.61(12) . . ? C69 C67 C70 107.13(12) . . ? C64 C67 C70 108.47(11) . . ? C46 C68 C62 114.53(8) . . ? C102 C101 C106 121.65(15) . . ? C102 C101 F101 120.41(16) . . ? C106 C101 F101 117.94(17) . . ? C101 C102 C103 118.25(19) . . ? F103 C103 C102 121.2(2) . . ? F103 C103 C104 118.44(17) . . ? C102 C103 C104 120.31(19) . . ? F104 C104 C105 119.0(2) . . ? F104 C104 C103 119.9(2) . . ? C105 C104 C103 121.07(16) . . ? C106 C105 C104 115.95(16) . . ? C101 C106 F106 118.91(13) . . ? C101 C106 C105 122.70(17) . . ? F106 C106 C105 118.38(15) . . ? C202 C201 C206 120.0 . . ? C202 C201 F201 115.6(6) . . ? C206 C201 F201 120.7(6) . . ? C203 C202 C201 120.0 . . ? F203 C203 C204 118.9(6) . . ? F203 C203 C202 117.2(6) . . ? C204 C203 C202 120.0 . . ? F204 C204 C203 121.6(6) . . ? F204 C204 C205 117.0(6) . . ? C203 C204 C205 120.0 . . ? C206 C205 C204 120.0 . . ? F206 C206 C205 139.0 . . ? F206 C206 C201 99.6 . . ? C205 C206 C201 120.0 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.286 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.042 #===END data_p2c _database_code_depnum_ccdc_archive 'CCDC 237577' _audit_creation_method SHELXL-97 _chemical_name_systematic ; p-tert-butyl-calix[4]arene*pentafluorobenzene ; _chemical_name_common p-tert-butyl-calix(4)arene*pentafluorobenzene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H57 F5 O4' _chemical_formula_weight 816.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 17.9842(18) _cell_length_b 13.6634(14) _cell_length_c 17.9165(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.262(2) _cell_angle_gamma 90.00 _cell_volume 4402.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1736 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9784 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(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 'CCD Bruker Smart 1000' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 39044 _diffrn_reflns_av_R_equivalents 0.1132 _diffrn_reflns_av_sigmaI/netI 0.0895 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 24.79 _reflns_number_total 7713 _reflns_number_gt 4269 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0890P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7713 _refine_ls_number_parameters 633 _refine_ls_number_restraints 73 _refine_ls_R_factor_all 0.1293 _refine_ls_R_factor_gt 0.0627 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 0.936 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.03470(15) 0.55954(18) 0.14752(15) 0.0347(7) Uani 1 1 d . . . H01 H -0.0077 0.5632 0.1640 0.052 Uiso 1 1 calc R . . O2 O 0.09779(15) 0.55524(18) 0.28430(15) 0.0346(7) Uani 1 1 d . . . H02 H 0.0876 0.5602 0.2398 0.052 Uiso 1 1 calc R . . O3 O 0.60176(15) 0.46637(18) 0.28332(15) 0.0331(7) Uani 1 1 d . . . H03 H 0.5822 0.4649 0.2419 0.050 Uiso 1 1 calc R . . O4 O 0.53093(15) 0.47103(19) 0.15222(14) 0.0330(7) Uani 1 1 d . . . H04 H 0.4880 0.4720 0.1673 0.049 Uiso 1 1 calc R . . C1 C 0.0440(2) 0.4699(3) 0.1121(2) 0.0263(10) Uani 1 1 d . . . C2 C -0.0146(2) 0.4256(3) 0.0740(2) 0.0300(10) Uani 1 1 d . . . C3 C -0.0011(2) 0.3363(3) 0.0381(2) 0.0316(10) Uani 1 1 d . . . H3 H -0.0397 0.3061 0.0123 0.038 Uiso 1 1 calc R . . C4 C 0.0680(2) 0.2914(3) 0.0401(2) 0.0302(10) Uani 1 1 d . . . C5 C 0.1237(2) 0.3386(3) 0.0790(2) 0.0282(10) Uani 1 1 d . . . H5 H 0.1703 0.3092 0.0812 0.034 Uiso 1 1 calc R . . C6 C 0.1142(2) 0.4276(3) 0.1150(2) 0.0273(10) Uani 1 1 d . . . C7 C 0.0826(2) 0.1931(3) 0.0000(2) 0.0400(11) Uani 1 1 d . . . C8 C -0.0924(2) 0.4697(3) 0.0708(2) 0.0307(10) Uani 1 1 d . . . H8A H -0.0889 0.5403 0.0753 0.037 Uiso 1 1 calc R . . H8B H -0.1149 0.4549 0.0228 0.037 Uiso 1 1 calc R . . C9 C 0.1178(3) 0.1198(3) 0.0556(3) 0.0519(13) Uani 1 1 d . . . H9A H 0.1629 0.1469 0.0756 0.078 Uiso 1 1 calc R . . H9B H 0.1286 0.0596 0.0302 0.078 Uiso 1 1 calc R . . H9C H 0.0836 0.1073 0.0955 0.078 Uiso 1 1 calc R . . C10 C 0.1370(3) 0.2107(4) -0.0637(3) 0.0530(13) Uani 1 1 d . . . H10A H 0.1140 0.2516 -0.1008 0.080 Uiso 1 1 calc R . . H10B H 0.1505 0.1492 -0.0857 0.080 Uiso 1 1 calc R . . H10C H 0.1808 0.2425 -0.0446 0.080 Uiso 1 1 calc R . . C11 C 0.0119(3) 0.1474(4) -0.0313(3) 0.0642(16) Uani 1 1 d . . . H11A H -0.0084 0.1891 -0.0694 0.096 Uiso 1 1 calc R . . H11B H -0.0238 0.1398 0.0080 0.096 Uiso 1 1 calc R . . H11C H 0.0232 0.0845 -0.0523 0.096 Uiso 1 1 calc R . . C21 C 0.1408(2) 0.4716(3) 0.2959(2) 0.0278(10) Uani 1 1 d . . . C22 C 0.1822(2) 0.4324(3) 0.2381(2) 0.0256(9) Uani 1 1 d . . . C23 C 0.2258(2) 0.3503(3) 0.2531(2) 0.0283(10) Uani 1 1 d . . . H23 H 0.2536 0.3233 0.2146 0.034 Uiso 1 1 calc R . . C24 C 0.2294(2) 0.3068(3) 0.3239(2) 0.0297(10) Uani 1 1 d . . . C25 C 0.1868(2) 0.3486(3) 0.3799(2) 0.0303(10) Uani 1 1 d . . . H25 H 0.1882 0.3211 0.4274 0.036 Uiso 1 1 calc R . . C26 C 0.1418(2) 0.4306(3) 0.3676(2) 0.0290(10) Uani 1 1 d . . . C27 C 0.2805(2) 0.2179(3) 0.3364(2) 0.0354(11) Uani 1 1 d . . . C28 C 0.1780(2) 0.4723(3) 0.1587(2) 0.0273(10) Uani 1 1 d . . . H28A H 0.1718 0.5427 0.1605 0.033 Uiso 1 1 calc R . . H28B H 0.2244 0.4584 0.1333 0.033 Uiso 1 1 calc R . . C29 C 0.2686(3) 0.1707(3) 0.4132(2) 0.0555(14) Uani 1 1 d . . . H29A H 0.2992 0.1134 0.4176 0.083 Uiso 1 1 calc R . . H29B H 0.2173 0.1527 0.4185 0.083 Uiso 1 1 calc R . . H29C H 0.2819 0.2165 0.4516 0.083 Uiso 1 1 calc R . . C30 C 0.3617(2) 0.2518(3) 0.3320(3) 0.0451(12) Uani 1 1 d . . . H30A H 0.3941 0.1965 0.3384 0.068 Uiso 1 1 calc R . . H30B H 0.3714 0.2988 0.3707 0.068 Uiso 1 1 calc R . . H30C H 0.3706 0.2813 0.2843 0.068 Uiso 1 1 calc R . . C31 C 0.2661(3) 0.1407(3) 0.2755(3) 0.0475(13) Uani 1 1 d . . . H31A H 0.3011 0.0880 0.2809 0.071 Uiso 1 1 calc R . . H31B H 0.2718 0.1701 0.2272 0.071 Uiso 1 1 calc R . . H31C H 0.2165 0.1157 0.2803 0.071 Uiso 1 1 calc R . . C41 C 0.6393(2) 0.5548(3) 0.2924(2) 0.0269(10) Uani 1 1 d . . . C42 C 0.6377(2) 0.5982(3) 0.3633(2) 0.0271(10) Uani 1 1 d . . . C43 C 0.6772(2) 0.6852(3) 0.3727(2) 0.0304(10) Uani 1 1 d . . . H43 H 0.6769 0.7150 0.4194 0.037 Uiso 1 1 calc R . . C44 C 0.7170(2) 0.7295(3) 0.3158(2) 0.0305(10) Uani 1 1 d . . . C45 C 0.7163(2) 0.6827(3) 0.2464(2) 0.0288(10) Uani 1 1 d . . . H45 H 0.7427 0.7105 0.2073 0.035 Uiso 1 1 calc R . . C46 C 0.6772(2) 0.5952(3) 0.2336(2) 0.0263(10) Uani 1 1 d . . . C47 C 0.7613(2) 0.8241(3) 0.3306(2) 0.0378(11) Uani 1 1 d . . . C48 C 0.5942(2) 0.5553(3) 0.4286(2) 0.0298(10) Uani 1 1 d . . . H48A H 0.5927 0.4846 0.4234 0.036 Uiso 1 1 calc R . . H48B H 0.6202 0.5703 0.4747 0.036 Uiso 1 1 calc R . . C49 C 0.7957(3) 0.8662(4) 0.2601(3) 0.0600(15) Uani 1 1 d . . . H49A H 0.8311 0.8206 0.2403 0.090 Uiso 1 1 calc R . . H49B H 0.8203 0.9267 0.2717 0.090 Uiso 1 1 calc R . . H49C H 0.7574 0.8778 0.2237 0.090 Uiso 1 1 calc R . . C50 C 0.7096(3) 0.9028(3) 0.3641(3) 0.0534(13) Uani 1 1 d . . . H50A H 0.6902 0.8799 0.4108 0.080 Uiso 1 1 calc R . . H50B H 0.6693 0.9153 0.3302 0.080 Uiso 1 1 calc R . . H50C H 0.7372 0.9620 0.3721 0.080 Uiso 1 1 calc R . . C51 C 0.8237(3) 0.8016(4) 0.3867(3) 0.0559(14) Uani 1 1 d . . . H51A H 0.8025 0.7772 0.4322 0.084 Uiso 1 1 calc R . . H51B H 0.8512 0.8604 0.3971 0.084 Uiso 1 1 calc R . . H51C H 0.8564 0.7533 0.3661 0.084 Uiso 1 1 calc R . . C61 C 0.5437(2) 0.5526(3) 0.1082(2) 0.0281(10) Uani 1 1 d . . . C62 C 0.6148(2) 0.5906(3) 0.1051(2) 0.0254(9) Uani 1 1 d . . . C63 C 0.6280(2) 0.6680(3) 0.0570(2) 0.0277(10) Uani 1 1 d . . . H63 H 0.6761 0.6927 0.0538 0.033 Uiso 1 1 calc R . . C64 C 0.5729(2) 0.7103(3) 0.0133(2) 0.0296(10) Uani 1 1 d . . . C65 C 0.5019(2) 0.6720(3) 0.0190(2) 0.0311(10) Uani 1 1 d . . . H65 H 0.4640 0.6993 -0.0097 0.037 Uiso 1 1 calc R . . C66 C 0.4851(2) 0.5935(3) 0.0661(2) 0.0262(10) Uani 1 1 d . . . C67 C 0.5877(2) 0.7955(3) -0.0419(2) 0.0341(10) Uani 1 1 d . . . C68 C 0.6773(2) 0.5512(3) 0.1554(2) 0.0268(10) Uani 1 1 d . . . H68A H 0.6723 0.4807 0.1593 0.032 Uiso 1 1 calc R . . H68B H 0.7248 0.5648 0.1321 0.032 Uiso 1 1 calc R . . C69 C 0.5766(3) 0.7577(3) -0.1216(2) 0.0478(12) Uani 1 1 d . . . H69A H 0.6111 0.7056 -0.1310 0.072 Uiso 1 1 calc R . . H69B H 0.5850 0.8100 -0.1563 0.072 Uiso 1 1 calc R . . H69C H 0.5267 0.7337 -0.1273 0.072 Uiso 1 1 calc R . . C70 C 0.5315(3) 0.8787(3) -0.0276(3) 0.0517(13) Uani 1 1 d . . . H70A H 0.5359 0.9003 0.0233 0.078 Uiso 1 1 calc R . . H70B H 0.4820 0.8552 -0.0365 0.078 Uiso 1 1 calc R . . H70C H 0.5418 0.9324 -0.0605 0.078 Uiso 1 1 calc R . . C71 C 0.6652(3) 0.8350(4) -0.0343(3) 0.0615(15) Uani 1 1 d . . . H71A H 0.6724 0.8603 0.0152 0.092 Uiso 1 1 calc R . . H71B H 0.6725 0.8866 -0.0700 0.092 Uiso 1 1 calc R . . H71C H 0.7004 0.7836 -0.0433 0.092 Uiso 1 1 calc R . . F1 F 0.5061(13) 0.6872(3) 0.2535(16) 0.082(2) Uani 0.50 1 d PD A -1 F2 F 0.5981(3) 0.8186(5) 0.1661(3) 0.085(2) Uani 0.50 1 d PD A -1 F5 F 0.3890(4) 0.9537(5) 0.3526(3) 0.086(2) Uani 0.50 1 d PD A -1 F4 F 0.4707(4) 1.0792(3) 0.2690(4) 0.082(3) Uani 0.50 1 d PD A -1 F3 F 0.5737(4) 1.0075(5) 0.1748(4) 0.081(2) Uani 0.50 1 d PD A -1 C101 C 0.5050(7) 0.7852(4) 0.2510(8) 0.0389(17) Uani 0.50 1 d PD A -1 C102 C 0.5459(4) 0.8482(7) 0.2094(5) 0.0459(16) Uiso 0.50 1 d PD A -1 C103 C 0.5335(5) 0.9456(7) 0.2165(5) 0.045(4) Uani 0.50 1 d PD A -1 C104 C 0.4814(6) 0.9818(6) 0.2642(8) 0.049(5) Uani 0.50 1 d PD A -1 C105 C 0.4405(6) 0.9173(7) 0.3063(5) 0.049(3) Uani 0.50 1 d PD A -1 C106 C 0.4522(6) 0.8184(7) 0.2997(6) 0.0459(16) Uiso 0.50 1 d PD A -1 H106 H 0.4247 0.7744 0.3280 0.055 Uiso 0.50 1 calc PR A -1 F11 F 0.0042(11) 0.3138(3) 0.2612(9) 0.078(3) Uani 0.50 1 d PD B -3 F12 F 0.0810(3) 0.1850(5) 0.3486(4) 0.081(2) Uani 0.50 1 d PD B -3 F13 F 0.0743(4) -0.0050(6) 0.3270(4) 0.090(2) Uani 0.50 1 d PD B -3 F14 F -0.0194(4) -0.0780(4) 0.2192(4) 0.088(3) Uani 0.50 1 d PD B -3 F15 F -0.1002(4) 0.0458(6) 0.1338(4) 0.093(2) Uani 0.50 1 d PD B -3 C201 C -0.0017(7) 0.2163(4) 0.2526(8) 0.051(2) Uani 0.50 1 d PD B -3 C202 C 0.0370(5) 0.1503(10) 0.2939(6) 0.075(6) Uani 0.50 1 d PD B -3 C203 C 0.0318(5) 0.0531(8) 0.2838(6) 0.055(4) Uani 0.50 1 d PD B -3 C204 C -0.0107(9) 0.0184(7) 0.2285(7) 0.066(6) Uani 0.50 1 d PD B -3 C205 C -0.0554(7) 0.0803(8) 0.1888(7) 0.067(4) Uani 0.50 1 d PD B -3 C206 C -0.0476(7) 0.1791(9) 0.1982(6) 0.040(3) Uani 0.50 1 d PD B -3 H206 H -0.0739 0.2216 0.1673 0.048 Uiso 0.50 1 calc PR B -3 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0340(16) 0.0223(15) 0.0479(17) 0.0033(13) 0.0019(13) 0.0022(13) O2 0.0393(17) 0.0241(15) 0.0403(16) 0.0009(12) -0.0025(13) 0.0046(13) O3 0.0400(17) 0.0201(14) 0.0391(16) 0.0000(12) -0.0061(13) -0.0012(13) O4 0.0342(16) 0.0256(15) 0.0391(17) 0.0031(12) 0.0018(13) -0.0001(13) C1 0.034(2) 0.021(2) 0.024(2) -0.0001(16) 0.0033(17) 0.0021(18) C2 0.032(2) 0.033(2) 0.026(2) 0.0108(18) -0.0030(18) -0.0004(19) C3 0.031(2) 0.036(2) 0.028(2) 0.0016(18) -0.0026(17) -0.0092(19) C4 0.029(2) 0.031(2) 0.031(2) 0.0008(18) 0.0039(17) 0.0019(19) C5 0.024(2) 0.030(2) 0.031(2) 0.0002(17) 0.0003(17) 0.0013(18) C6 0.029(2) 0.027(2) 0.026(2) 0.0104(17) 0.0066(17) -0.0041(18) C7 0.030(2) 0.044(3) 0.045(3) -0.015(2) -0.0009(19) 0.003(2) C8 0.032(2) 0.027(2) 0.033(2) 0.0021(18) -0.0066(18) 0.0025(18) C9 0.054(3) 0.033(3) 0.069(3) -0.007(2) 0.005(2) 0.007(2) C10 0.056(3) 0.057(3) 0.046(3) -0.014(2) 0.007(2) 0.010(3) C11 0.049(3) 0.056(3) 0.087(4) -0.035(3) -0.002(3) 0.002(3) C21 0.027(2) 0.020(2) 0.036(2) -0.0012(17) -0.0046(18) -0.0049(18) C22 0.023(2) 0.023(2) 0.031(2) -0.0013(17) -0.0016(17) -0.0054(17) C23 0.026(2) 0.032(2) 0.027(2) -0.0026(17) 0.0039(16) -0.0011(18) C24 0.036(2) 0.021(2) 0.032(2) -0.0005(17) -0.0025(18) -0.0010(18) C25 0.029(2) 0.032(2) 0.030(2) -0.0005(18) 0.0012(18) -0.0079(19) C26 0.025(2) 0.029(2) 0.033(2) -0.0077(18) 0.0001(17) -0.0066(18) C27 0.045(3) 0.030(2) 0.031(2) -0.0001(18) 0.0023(19) 0.003(2) C28 0.029(2) 0.024(2) 0.029(2) 0.0023(17) 0.0010(17) 0.0001(18) C29 0.079(4) 0.041(3) 0.047(3) 0.006(2) 0.008(2) 0.014(3) C30 0.048(3) 0.026(2) 0.061(3) -0.003(2) -0.013(2) 0.007(2) C31 0.060(3) 0.026(2) 0.056(3) -0.004(2) -0.004(2) 0.007(2) C41 0.024(2) 0.024(2) 0.033(2) 0.0012(17) -0.0028(17) 0.0067(17) C42 0.020(2) 0.031(2) 0.031(2) 0.0003(18) -0.0001(17) 0.0006(18) C43 0.030(2) 0.031(2) 0.030(2) -0.0061(18) -0.0035(18) 0.0044(19) C44 0.032(2) 0.027(2) 0.033(2) -0.0003(18) 0.0025(18) 0.0021(18) C45 0.025(2) 0.033(2) 0.028(2) 0.0086(18) 0.0061(17) 0.0014(18) C46 0.021(2) 0.024(2) 0.034(2) 0.0010(18) -0.0019(17) 0.0009(18) C47 0.043(3) 0.033(2) 0.037(2) -0.0013(19) 0.003(2) -0.008(2) C48 0.030(2) 0.031(2) 0.028(2) -0.0006(18) -0.0029(18) 0.0015(18) C49 0.085(4) 0.045(3) 0.050(3) -0.003(2) 0.021(3) -0.025(3) C50 0.071(3) 0.024(2) 0.065(3) -0.008(2) 0.005(3) -0.005(2) C51 0.049(3) 0.052(3) 0.067(3) -0.009(3) -0.006(2) -0.014(3) C61 0.039(3) 0.024(2) 0.021(2) -0.0018(17) 0.0026(18) 0.0023(19) C62 0.024(2) 0.026(2) 0.026(2) -0.0047(17) 0.0018(16) 0.0035(18) C63 0.023(2) 0.029(2) 0.030(2) -0.0014(17) 0.0010(17) -0.0002(18) C64 0.037(2) 0.025(2) 0.027(2) -0.0007(17) 0.0046(18) 0.0016(19) C65 0.035(2) 0.028(2) 0.030(2) 0.0001(18) 0.0011(18) 0.0057(19) C66 0.029(2) 0.025(2) 0.025(2) -0.0093(17) 0.0009(17) 0.0004(18) C67 0.040(2) 0.028(2) 0.035(2) 0.0065(18) 0.0066(19) 0.002(2) C68 0.026(2) 0.024(2) 0.030(2) 0.0004(17) 0.0016(17) 0.0013(18) C69 0.060(3) 0.037(3) 0.046(3) 0.012(2) 0.006(2) 0.005(2) C70 0.068(3) 0.031(3) 0.056(3) 0.005(2) 0.009(2) 0.006(2) C71 0.054(3) 0.053(3) 0.077(4) 0.026(3) -0.001(3) -0.013(3) F1 0.130(7) 0.030(2) 0.085(5) -0.005(9) -0.052(5) 0.014(9) F2 0.091(5) 0.086(5) 0.079(4) 0.006(4) 0.022(4) 0.021(4) F5 0.096(5) 0.094(5) 0.066(4) 0.017(4) 0.032(4) 0.053(4) F4 0.129(7) 0.032(3) 0.084(6) -0.004(3) -0.014(4) 0.011(3) F3 0.075(5) 0.070(5) 0.098(5) 0.038(4) 0.004(4) -0.027(4) C101 0.037(4) 0.031(3) 0.049(4) -0.010(16) -0.009(4) -0.007(11) C103 0.049(8) 0.030(7) 0.056(8) 0.008(6) 0.006(5) -0.015(6) C104 0.048(11) 0.024(5) 0.073(12) -0.008(7) -0.017(7) 0.003(5) C105 0.060(8) 0.048(8) 0.038(6) 0.017(5) 0.012(5) 0.004(6) F11 0.085(5) 0.043(2) 0.105(9) -0.013(5) 0.007(6) -0.021(7) F12 0.073(4) 0.084(5) 0.086(5) -0.021(4) -0.002(4) -0.005(4) F13 0.106(6) 0.102(6) 0.064(4) 0.028(4) 0.012(4) 0.062(5) F14 0.101(6) 0.033(3) 0.129(7) -0.009(3) 0.028(4) 0.001(4) F15 0.082(5) 0.101(6) 0.097(6) -0.045(5) -0.020(4) 0.012(4) C201 0.047(4) 0.042(4) 0.066(6) -0.046(10) 0.014(5) 0.003(15) C202 0.047(9) 0.121(15) 0.057(9) -0.034(9) 0.002(6) 0.006(9) C203 0.040(8) 0.048(8) 0.079(10) 0.024(7) 0.030(6) 0.026(7) C204 0.093(12) 0.041(6) 0.064(13) -0.003(5) 0.033(10) 0.028(9) C205 0.052(9) 0.052(9) 0.098(11) -0.016(8) 0.001(7) -0.001(7) C206 0.044(7) 0.060(7) 0.016(5) 0.002(5) -0.014(5) 0.020(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.389(4) . ? O2 C21 1.395(5) . ? O3 C41 1.393(5) . ? O4 C61 1.385(5) . ? C1 C6 1.388(5) . ? C1 C2 1.393(5) . ? C2 C3 1.401(6) . ? C2 C8 1.525(5) . ? C3 C4 1.386(5) . ? C4 C5 1.379(5) . ? C4 C7 1.545(6) . ? C5 C6 1.387(5) . ? C6 C28 1.515(5) . ? C7 C11 1.522(6) . ? C7 C10 1.526(6) . ? C7 C9 1.546(6) . ? C8 C26 1.516(5) 2 ? C21 C22 1.385(5) . ? C21 C26 1.402(6) . ? C22 C23 1.394(5) . ? C22 C28 1.525(5) . ? C23 C24 1.402(5) . ? C24 C25 1.389(5) . ? C24 C27 1.539(5) . ? C25 C26 1.399(5) . ? C26 C8 1.516(5) 2 ? C27 C30 1.535(6) . ? C27 C29 1.536(6) . ? C27 C31 1.539(6) . ? C41 C46 1.373(5) . ? C41 C42 1.403(5) . ? C42 C43 1.395(6) . ? C42 C48 1.527(5) . ? C43 C44 1.386(5) . ? C44 C45 1.398(6) . ? C44 C47 1.541(6) . ? C45 C46 1.406(5) . ? C46 C68 1.524(5) . ? C47 C49 1.523(6) . ? C47 C51 1.535(6) . ? C47 C50 1.544(6) . ? C48 C66 1.521(5) 2_655 ? C61 C62 1.382(6) . ? C61 C66 1.407(5) . ? C62 C63 1.385(5) . ? C62 C68 1.535(5) . ? C63 C64 1.386(5) . ? C64 C65 1.384(6) . ? C64 C67 1.552(5) . ? C65 C66 1.399(6) . ? C66 C48 1.521(5) 2_655 ? C67 C71 1.501(6) . ? C67 C69 1.530(6) . ? C67 C70 1.543(6) . ? F1 C101 1.339(6) . ? F2 C102 1.286(9) . ? F5 C105 1.342(9) . ? F4 C104 1.347(8) . ? F3 C103 1.342(10) . ? C101 C102 1.357(12) . ? C101 C106 1.369(14) . ? C102 C103 1.356(11) . ? C103 C104 1.364(12) . ? C104 C105 1.376(12) . ? C105 C106 1.373(12) . ? F11 C201 1.345(7) . ? F12 C202 1.343(10) . ? F13 C203 1.344(10) . ? F14 C204 1.337(10) . ? F15 C205 1.355(11) . ? C201 C202 1.356(14) . ? C201 C206 1.372(14) . ? C202 C203 1.345(14) . ? C203 C204 1.336(14) . ? C204 C205 1.365(14) . ? C205 C206 1.367(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 O1 117.5(3) . . ? C6 C1 C2 121.5(4) . . ? O1 C1 C2 121.0(3) . . ? C1 C2 C3 118.1(4) . . ? C1 C2 C8 122.6(4) . . ? C3 C2 C8 119.2(4) . . ? C4 C3 C2 122.1(4) . . ? C5 C4 C3 117.0(4) . . ? C5 C4 C7 121.2(4) . . ? C3 C4 C7 121.8(4) . . ? C4 C5 C6 123.7(4) . . ? C5 C6 C1 117.5(4) . . ? C5 C6 C28 119.9(4) . . ? C1 C6 C28 122.5(3) . . ? C11 C7 C10 109.1(4) . . ? C11 C7 C4 112.6(3) . . ? C10 C7 C4 108.7(4) . . ? C11 C7 C9 108.1(4) . . ? C10 C7 C9 108.8(3) . . ? C4 C7 C9 109.5(3) . . ? C26 C8 C2 112.0(3) 2 . ? C22 C21 O2 120.4(3) . . ? C22 C21 C26 121.7(4) . . ? O2 C21 C26 117.9(3) . . ? C21 C22 C23 118.1(4) . . ? C21 C22 C28 122.3(3) . . ? C23 C22 C28 119.5(3) . . ? C22 C23 C24 122.6(4) . . ? C25 C24 C23 117.1(4) . . ? C25 C24 C27 123.4(4) . . ? C23 C24 C27 119.5(3) . . ? C24 C25 C26 122.4(4) . . ? C25 C26 C21 118.0(4) . . ? C25 C26 C8 120.5(4) . 2 ? C21 C26 C8 121.4(4) . 2 ? C30 C27 C29 108.0(4) . . ? C30 C27 C24 108.8(3) . . ? C29 C27 C24 112.1(3) . . ? C30 C27 C31 109.2(3) . . ? C29 C27 C31 108.9(4) . . ? C24 C27 C31 109.8(3) . . ? C6 C28 C22 111.9(3) . . ? C46 C41 O3 120.0(3) . . ? C46 C41 C42 122.5(4) . . ? O3 C41 C42 117.4(3) . . ? C43 C42 C41 117.2(4) . . ? C43 C42 C48 119.9(3) . . ? C41 C42 C48 122.9(4) . . ? C44 C43 C42 123.2(4) . . ? C43 C44 C45 116.9(4) . . ? C43 C44 C47 120.5(3) . . ? C45 C44 C47 122.6(3) . . ? C44 C45 C46 122.5(4) . . ? C41 C46 C45 117.7(4) . . ? C41 C46 C68 123.4(3) . . ? C45 C46 C68 118.9(3) . . ? C49 C47 C51 108.7(4) . . ? C49 C47 C44 112.7(3) . . ? C51 C47 C44 108.7(4) . . ? C49 C47 C50 107.9(4) . . ? C51 C47 C50 108.9(4) . . ? C44 C47 C50 109.8(3) . . ? C66 C48 C42 113.6(3) 2_655 . ? C62 C61 O4 118.7(4) . . ? C62 C61 C66 121.3(4) . . ? O4 C61 C66 119.9(4) . . ? C61 C62 C63 118.2(4) . . ? C61 C62 C68 121.3(3) . . ? C63 C62 C68 120.4(4) . . ? C62 C63 C64 123.1(4) . . ? C65 C64 C63 117.3(4) . . ? C65 C64 C67 119.5(4) . . ? C63 C64 C67 123.3(4) . . ? C64 C65 C66 122.4(4) . . ? C65 C66 C61 117.7(4) . . ? C65 C66 C48 120.4(4) . 2_655 ? C61 C66 C48 121.9(4) . 2_655 ? C71 C67 C69 108.8(4) . . ? C71 C67 C70 109.2(4) . . ? C69 C67 C70 108.8(4) . . ? C71 C67 C64 112.0(3) . . ? C69 C67 C64 108.6(3) . . ? C70 C67 C64 109.4(3) . . ? C46 C68 C62 113.4(3) . . ? F1 C101 C102 130.1(16) . . ? F1 C101 C106 108.7(15) . . ? C102 C101 C106 121.2(7) . . ? F2 C102 C103 119.1(9) . . ? F2 C102 C101 122.0(9) . . ? C103 C102 C101 118.8(8) . . ? F3 C103 C102 118.5(9) . . ? F3 C103 C104 119.6(8) . . ? C102 C103 C104 121.9(8) . . ? F4 C104 C103 119.8(8) . . ? F4 C104 C105 121.4(9) . . ? C103 C104 C105 118.8(8) . . ? F5 C105 C106 121.7(8) . . ? F5 C105 C104 118.3(9) . . ? C106 C105 C104 120.0(9) . . ? C101 C106 C105 119.2(9) . . ? F11 C201 C202 123.7(13) . . ? F11 C201 C206 119.7(13) . . ? C202 C201 C206 116.5(8) . . ? F12 C202 C203 119.1(11) . . ? F12 C202 C201 117.6(12) . . ? C203 C202 C201 123.3(9) . . ? C204 C203 F13 122.7(10) . . ? C204 C203 C202 119.3(9) . . ? F13 C203 C202 117.8(10) . . ? C203 C204 F14 120.5(9) . . ? C203 C204 C205 120.0(9) . . ? F14 C204 C205 118.6(11) . . ? F15 C205 C204 120.6(11) . . ? F15 C205 C206 119.6(10) . . ? C204 C205 C206 119.2(11) . . ? C205 C206 C201 121.0(11) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 24.79 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.249 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.054 #===END data_ku121 _database_code_depnum_ccdc_archive 'CCDC 237578' _audit_creation_method SHELXL-97 _chemical_name_systematic ; p-tert-butyl-calix[4]arene*1,3,4,5-tetrafluorobenzene ; _chemical_name_common p-tert-butyl-calix(4)arene*1,3,4,5-tetrafluorobenzene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H58 F4 O4' _chemical_formula_weight 798.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 12.6344(9) _cell_length_b 13.5174(9) _cell_length_c 12.6433(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.0500(10) _cell_angle_gamma 90.00 _cell_volume 2159.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 852 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9784 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD Bruker Smart 1000' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25832 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 28.81 _reflns_number_total 5589 _reflns_number_gt 4207 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0604P)^2^+0.8525P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0033(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5589 _refine_ls_number_parameters 438 _refine_ls_number_restraints 148 _refine_ls_R_factor_all 0.0744 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1417 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.128 _refine_ls_shift/su_max 0.036 _refine_ls_shift/su_mean 0.004 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 F1A F 0.7538(5) 1.16906(13) 0.2475(3) 0.0268(5) Uani 0.26 1 d PD A -6 F3A F 0.56512(19) 1.46517(17) 0.25389(17) 0.0299(5) Uani 0.26 1 d PDU A -6 F4A F 0.7399(3) 1.56948(12) 0.2533(2) 0.0323(6) Uani 0.26 1 d PD A -6 F5A F 0.93203(17) 1.49269(6) 0.25234(14) 0.162(3) Uani 0.26 1 d PD A -6 C1A C 0.74482(17) 1.26357(6) 0.24970(14) 0.0555(13) Uani 0.26 1 d PRD A -6 C2A C 0.64964(17) 1.31511(6) 0.25150(14) 0.0300(11) Uani 0.26 1 d PRD A -6 H2A H 0.5845 1.2801 0.2527 0.036 Uiso 0.26 1 calc PR A -6 C3A C 0.64980(17) 1.41794(6) 0.25157(14) 0.076(2) Uani 0.26 1 d PRD A -6 C4A C 0.74514(17) 1.46923(6) 0.24985(14) 0.0371(9) Uani 0.26 1 d PRD A -6 C5A C 0.84032(17) 1.41770(6) 0.24805(14) 0.0226(8) Uani 0.26 1 d PRDU A -6 C6A C 0.84016(17) 1.31487(6) 0.24797(14) 0.0609(19) Uani 0.26 1 d PRD A -6 H6A H 0.9052 1.2796 0.2467 0.073 Uiso 0.26 1 calc PR A -6 F1B F 0.74822(17) 1.16893(6) 0.26200(14) 0.0658(13) Uani 0.24 1 d PRD A -7 F3B F 0.73881(17) 1.47237(6) 0.06995(14) 0.0570(11) Uani 0.24 1 d PRD A -7 F4B F 0.74034(17) 1.56915(6) 0.23331(14) 0.094(2) Uani 0.24 1 d PRD A -7 F5B F 0.74565(17) 1.46703(6) 0.43907(14) 0.0613(13) Uani 0.24 1 d PRD A -7 C1B C 0.74683(17) 1.26568(6) 0.25316(14) 0.0169(7) Uani 0.24 1 d PRDU A -7 C2B C 0.74369(17) 1.31610(6) 0.15740(14) 0.0304(13) Uani 0.24 1 d PRD A -7 H2B H 0.7432 1.2803 0.0927 0.037 Uiso 0.24 1 calc PR A -7 C3B C 0.74122(17) 1.41890(6) 0.15624(14) 0.0319(12) Uani 0.24 1 d PRD A -7 C4B C 0.74189(17) 1.47128(6) 0.25085(14) 0.0493(16) Uani 0.24 1 d PRD A -7 C5B C 0.74503(17) 1.42085(6) 0.34662(14) 0.0450(18) Uani 0.24 1 d PRD A -7 C6B C 0.74750(17) 1.31806(6) 0.34777(14) 0.0404(17) Uani 0.24 1 d PRD A -7 H6B H 0.7496 1.2836 0.4132 0.049 Uiso 0.24 1 calc PR A -7 C8 C 0.55071(19) 1.29265(18) -0.12318(19) 0.0347(6) Uani 0.50 1 d PD B -1 C9 C 0.4614(2) 1.2567(2) -0.1969(2) 0.0441(7) Uani 0.50 1 d PD B -1 H9A H 0.4336 1.3128 -0.2374 0.053 Uiso 0.50 1 calc PR B -1 H9B H 0.4044 1.2276 -0.1545 0.053 Uiso 0.50 1 calc PR B -1 H9C H 0.4893 1.2068 -0.2457 0.053 Uiso 0.50 1 calc PR B -1 C10 C 0.5030(2) 1.3744(2) -0.0523(2) 0.0481(8) Uani 0.50 1 d PD B -1 H10A H 0.4409 1.3484 -0.0152 0.058 Uiso 0.50 1 calc PR B -1 H10B H 0.4819 1.4308 -0.0963 0.058 Uiso 0.50 1 calc PR B -1 H10C H 0.5560 1.3960 -0.0006 0.058 Uiso 0.50 1 calc PR B -1 C11 C 0.6372(2) 1.3383(2) -0.1898(3) 0.0575(9) Uani 0.50 1 d PD B -1 H11A H 0.6637 1.2891 -0.2402 0.069 Uiso 0.50 1 calc PR B -1 H11B H 0.6952 1.3601 -0.1439 0.069 Uiso 0.50 1 calc PR B -1 H11C H 0.6088 1.3952 -0.2285 0.069 Uiso 0.50 1 calc PR B -1 C8K C 0.5745(2) 1.3175(2) -0.0882(2) 0.0418(7) Uani 0.50 1 d PD B -2 C9K C 0.5684(2) 1.2964(2) -0.2085(2) 0.0494(8) Uani 0.50 1 d PD B -2 H9K1 H 0.5106 1.2499 -0.2226 0.059 Uiso 0.50 1 calc PR B -2 H9K2 H 0.6355 1.2675 -0.2324 0.059 Uiso 0.50 1 calc PR B -2 H9K3 H 0.5554 1.3583 -0.2466 0.059 Uiso 0.50 1 calc PR B -2 C10K C 0.4703(3) 1.3586(3) -0.0518(3) 0.0682(11) Uani 0.50 1 d PD B -2 H101 H 0.4742 1.3738 0.0239 0.082 Uiso 0.50 1 calc PR B -2 H102 H 0.4144 1.3097 -0.0643 0.082 Uiso 0.50 1 calc PR B -2 H103 H 0.4544 1.4191 -0.0914 0.082 Uiso 0.50 1 calc PR B -2 C11K C 0.6631(2) 1.3925(2) -0.0689(3) 0.0559(9) Uani 0.50 1 d PD B -2 H11D H 0.6469 1.4541 -0.1064 0.067 Uiso 0.50 1 calc PR B -2 H11E H 0.7302 1.3656 -0.0950 0.067 Uiso 0.50 1 calc PR B -2 H11F H 0.6690 1.4058 0.0071 0.067 Uiso 0.50 1 calc PR B -2 C19 C 1.0900(2) 1.3193(2) 0.0729(2) 0.0417(7) Uani 0.50 1 d PD B -3 C20 C 1.0710(3) 1.3959(2) 0.1597(2) 0.0548(9) Uani 0.50 1 d PD B -3 H20A H 1.1109 1.4563 0.1436 0.066 Uiso 0.50 1 calc PR B -3 H20B H 1.0947 1.3692 0.2278 0.066 Uiso 0.50 1 calc PR B -3 H20C H 0.9954 1.4115 0.1634 0.066 Uiso 0.50 1 calc PR B -3 C21 C 1.2100(2) 1.2977(2) 0.0671(2) 0.0485(8) Uani 0.50 1 d PD B -3 H21A H 1.2239 1.2508 0.0096 0.058 Uiso 0.50 1 calc PR B -3 H21B H 1.2339 1.2693 0.1343 0.058 Uiso 0.50 1 calc PR B -3 H21C H 1.2484 1.3595 0.0536 0.058 Uiso 0.50 1 calc PR B -3 C22 C 1.0539(3) 1.3588(2) -0.0316(3) 0.0678(11) Uani 0.50 1 d PD B -3 H22A H 1.0894 1.4218 -0.0458 0.081 Uiso 0.50 1 calc PR B -3 H22B H 0.9771 1.3690 -0.0300 0.081 Uiso 0.50 1 calc PR B -3 H22C H 1.0716 1.3113 -0.0874 0.081 Uiso 0.50 1 calc PR B -3 C19K C 1.1216(2) 1.29141(18) 0.05172(19) 0.0337(6) Uani 0.50 1 d PD B -4 C20K C 1.1869(3) 1.3381(2) 0.1386(2) 0.0551(8) Uani 0.50 1 d PD B -4 H20D H 1.2384 1.2899 0.1652 0.066 Uiso 0.50 1 calc PR B -4 H20E H 1.1403 1.3588 0.1965 0.066 Uiso 0.50 1 calc PR B -4 H20F H 1.2244 1.3959 0.1106 0.066 Uiso 0.50 1 calc PR B -4 C21K C 1.1960(2) 1.2559(2) -0.0363(2) 0.0425(7) Uani 0.50 1 d PD B -4 H21D H 1.2372 1.3121 -0.0629 0.051 Uiso 0.50 1 calc PR B -4 H21E H 1.1543 1.2274 -0.0941 0.051 Uiso 0.50 1 calc PR B -4 H21F H 1.2442 1.2056 -0.0080 0.051 Uiso 0.50 1 calc PR B -4 C22K C 1.0504(3) 1.3735(2) 0.0028(3) 0.0484(9) Uani 0.50 1 d PD B -4 H22D H 1.0947 1.4291 -0.0201 0.058 Uiso 0.50 1 calc PR B -4 H22E H 0.9995 1.3966 0.0559 0.058 Uiso 0.50 1 calc PR B -4 H22F H 1.0121 1.3467 -0.0582 0.058 Uiso 0.50 1 calc PR B -4 O1 O 0.68297(7) 0.95639(7) 0.11703(7) 0.0400(2) Uani 1 1 d . . . H1 H 0.6338 0.9378 0.1570 0.048 Uiso 1 1 calc R . . O2 O 0.88310(7) 0.95651(7) 0.18318(7) 0.0382(2) Uani 1 1 d . . . H2 H 0.8424 0.9383 0.1343 0.046 Uiso 1 1 calc R . . C1 C 0.65325(9) 1.04192(9) 0.06566(9) 0.0306(3) Uani 1 1 d . B . C2 C 0.55447(9) 1.08448(9) 0.08415(9) 0.0314(3) Uani 1 1 d . . . C3 C 0.52783(10) 1.16878(10) 0.02871(10) 0.0386(3) Uani 1 1 d . B . H3 H 0.4605 1.1980 0.0409 0.046 Uiso 1 1 calc R . . C4 C 0.59551(11) 1.21310(11) -0.04459(12) 0.0483(4) Uani 1 1 d D . . C5 C 0.69373(10) 1.16821(11) -0.05984(11) 0.0405(3) Uani 1 1 d . B . H5 H 0.7413 1.1965 -0.1095 0.049 Uiso 1 1 calc R . . C6 C 0.72469(9) 1.08406(10) -0.00561(9) 0.0319(3) Uani 1 1 d . . . C7 C 0.83499(9) 1.04136(10) -0.02221(9) 0.0322(3) Uani 1 1 d . B . H7A H 0.8322 0.9687 -0.0131 0.039 Uiso 1 1 calc R . . H7B H 0.8580 1.0551 -0.0956 0.039 Uiso 1 1 calc R . . C12 C 0.93442(9) 1.04191(9) 0.15351(9) 0.0312(3) Uani 1 1 d . B . C13 C 0.91573(9) 1.08428(10) 0.05447(9) 0.0322(3) Uani 1 1 d . . . C14 C 0.97138(10) 1.16854(10) 0.02767(10) 0.0400(3) Uani 1 1 d . B . H14 H 0.9594 1.1973 -0.0398 0.048 Uiso 1 1 calc R . . C15 C 1.04441(12) 1.21333(12) 0.09536(10) 0.0492(4) Uani 1 1 d D . . C16 C 1.05948(11) 1.16870(11) 0.19377(10) 0.0425(3) Uani 1 1 d . B . H16 H 1.1088 1.1974 0.2415 0.051 Uiso 1 1 calc R . . C17 C 1.00557(9) 1.08429(10) 0.22471(9) 0.0330(3) Uani 1 1 d . . . C18 C 0.47753(9) 1.04189(10) 0.16494(9) 0.0330(3) Uani 1 1 d . . . H18A H 0.4862 0.9691 0.1676 0.040 Uiso 1 1 calc R . . H18B H 0.4042 1.0561 0.1419 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1A 0.0186(9) 0.0337(8) 0.0282(9) 0.017(2) 0.0002(7) 0.009(2) F3A 0.0264(9) 0.0257(9) 0.0375(10) 0.0098(8) 0.0038(8) 0.0150(7) F4A 0.0324(14) 0.0155(8) 0.0491(12) 0.005(2) 0.0052(10) 0.0015(15) F5A 0.116(4) 0.189(6) 0.181(6) -0.076(5) 0.027(4) -0.077(4) C1A 0.041(2) 0.070(2) 0.055(2) 0.003(5) 0.0043(19) 0.040(3) C2A 0.0163(16) 0.037(2) 0.037(2) 0.0063(18) 0.0020(16) 0.0219(15) C3A 0.066(4) 0.097(5) 0.065(4) 0.018(4) 0.007(4) 0.020(4) C4A 0.0465(19) 0.0197(13) 0.0450(18) 0.019(3) 0.0186(15) 0.026(3) C5A 0.0206(12) 0.0243(13) 0.0228(13) -0.0015(11) 0.0023(10) -0.0041(10) C6A 0.056(3) 0.090(4) 0.037(3) -0.010(3) -0.001(3) 0.044(3) F1B 0.097(3) 0.0394(15) 0.061(3) 0.009(3) 0.011(2) -0.005(4) F3B 0.072(2) 0.0476(18) 0.0516(19) 0.0291(15) -0.0024(18) -0.0052(17) F4B 0.123(5) 0.064(2) 0.096(5) 0.005(3) -0.027(4) 0.002(4) F5B 0.064(2) 0.077(3) 0.043(2) -0.0216(19) -0.0058(18) 0.023(2) C1B 0.0167(11) 0.0179(11) 0.0160(11) -0.0020(13) 0.0005(9) 0.0020(13) C2B 0.028(2) 0.027(2) 0.036(2) -0.006(2) 0.000(2) -0.0088(19) C3B 0.028(2) 0.047(3) 0.020(2) 0.011(2) 0.0017(17) -0.015(2) C4B 0.029(3) 0.072(4) 0.046(3) -0.007(8) -0.015(2) 0.009(5) C5B 0.026(2) 0.035(3) 0.074(4) -0.011(3) -0.017(3) -0.001(2) C6B 0.023(2) 0.079(4) 0.019(2) -0.011(3) 0.002(2) 0.004(3) C8 0.0364(12) 0.0337(11) 0.0339(11) -0.0064(10) 0.0097(10) 0.0028(10) C9 0.0516(15) 0.0420(13) 0.0387(13) 0.0012(11) -0.0089(12) 0.0031(12) C10 0.0514(16) 0.0444(14) 0.0485(15) -0.0103(13) 0.0026(13) 0.0008(13) C11 0.0445(15) 0.0519(15) 0.076(2) 0.0268(14) 0.0159(14) 0.0050(13) C8K 0.0442(14) 0.0448(14) 0.0364(13) -0.0054(11) 0.0158(11) -0.0063(12) C9K 0.0474(15) 0.0568(16) 0.0439(15) 0.0082(13) -0.0036(13) 0.0031(14) C10K 0.0582(19) 0.0550(18) 0.091(3) 0.0149(18) 0.0355(18) 0.0108(16) C11K 0.0611(17) 0.0473(15) 0.0593(17) -0.0050(13) 0.0189(15) -0.0185(13) C19 0.0362(13) 0.0447(14) 0.0440(14) -0.0034(12) -0.0093(11) 0.0026(11) C20 0.0552(17) 0.0503(15) 0.0590(17) -0.0144(14) -0.0130(14) 0.0024(14) C21 0.0367(13) 0.0581(16) 0.0506(16) 0.0012(13) 0.0038(12) -0.0087(12) C22 0.087(2) 0.0472(16) 0.069(2) 0.0005(15) -0.0345(18) -0.0140(16) C19K 0.0340(12) 0.0328(12) 0.0342(12) 0.0006(10) -0.0103(10) 0.0045(10) C20K 0.0695(18) 0.0484(15) 0.0475(15) 0.0060(13) -0.0161(14) -0.0205(14) C21K 0.0331(12) 0.0392(13) 0.0552(15) 0.0032(12) 0.0059(11) -0.0013(11) C22K 0.0491(16) 0.0384(14) 0.0576(18) -0.0028(13) -0.0078(14) 0.0106(13) O1 0.0282(4) 0.0587(5) 0.0330(4) 0.0075(4) 0.0013(3) -0.0020(4) O2 0.0298(4) 0.0538(5) 0.0310(4) -0.0030(4) -0.0009(3) -0.0049(4) C1 0.0237(5) 0.0458(6) 0.0223(5) -0.0040(5) -0.0019(4) -0.0031(5) C2 0.0221(5) 0.0495(6) 0.0225(5) -0.0026(5) -0.0013(4) -0.0069(5) C3 0.0244(5) 0.0532(7) 0.0381(6) 0.0013(6) 0.0065(5) 0.0016(5) C4 0.0343(6) 0.0541(8) 0.0564(8) 0.0137(7) 0.0169(6) 0.0038(6) C5 0.0287(6) 0.0522(7) 0.0406(6) 0.0041(6) 0.0112(5) -0.0025(5) C6 0.0210(5) 0.0510(6) 0.0237(5) -0.0057(5) 0.0000(4) -0.0040(5) C7 0.0210(5) 0.0546(7) 0.0210(5) -0.0052(5) 0.0009(4) -0.0006(5) C12 0.0209(5) 0.0460(6) 0.0267(5) -0.0024(5) 0.0030(4) 0.0030(5) C13 0.0210(5) 0.0529(7) 0.0227(5) -0.0056(5) 0.0009(4) 0.0010(5) C14 0.0347(6) 0.0604(7) 0.0251(5) 0.0034(6) -0.0047(5) -0.0063(6) C15 0.0490(7) 0.0663(9) 0.0323(6) 0.0059(6) -0.0128(6) -0.0193(7) C16 0.0361(6) 0.0625(8) 0.0288(6) -0.0018(6) -0.0095(5) -0.0103(6) C17 0.0213(5) 0.0551(7) 0.0227(5) -0.0028(5) 0.0000(4) 0.0030(5) C18 0.0208(5) 0.0558(7) 0.0224(5) 0.0015(5) -0.0010(4) -0.0054(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1A C1A 1.283(2) . ? F3A C3A 1.246(3) . ? F4A C4A 1.3574(19) . ? F5A C5A 1.5405 . ? C1A C2A 1.3900 . ? C1A C6A 1.3900 . ? C2A C3A 1.3900 . ? C3A C4A 1.3900 . ? C4A C5A 1.3900 . ? C5A C6A 1.3900 . ? F1B C1B 1.3127 . ? F3B C3B 1.3090 . ? F4B C4B 1.3416 . ? F5B C5B 1.3252 . ? C1B C2B 1.3900 . ? C1B C6B 1.3900 . ? C2B C3B 1.3900 . ? C3B C4B 1.3900 . ? C4B C5B 1.3900 . ? C5B C6B 1.3900 . ? C8 C11 1.512(4) . ? C8 C9 1.542(4) . ? C8 C10 1.545(4) . ? C8 C4 1.569(3) . ? C8K C10K 1.501(4) . ? C8K C11K 1.530(4) . ? C8K C4 1.538(3) . ? C8K C9K 1.549(4) . ? C19 C22 1.496(4) . ? C19 C20 1.528(4) . ? C19 C21 1.546(4) . ? C19 C15 1.570(3) . ? C19K C20K 1.512(4) . ? C19K C21K 1.534(4) . ? C19K C15 1.539(3) . ? C19K C22K 1.557(4) . ? O1 C1 1.3781(15) . ? O2 C12 1.3763(15) . ? C1 C2 1.3942(16) . ? C1 C6 1.3973(16) . ? C2 C3 1.3794(18) . ? C2 C18 1.5237(16) . ? C3 C4 1.3965(19) . ? C4 C5 1.3949(19) . ? C5 C6 1.3843(19) . ? C6 C7 1.5231(16) . ? C7 C13 1.5216(16) . ? C12 C17 1.3947(16) . ? C12 C13 1.3970(16) . ? C13 C14 1.3809(18) . ? C14 C15 1.3960(19) . ? C15 C16 1.3957(19) . ? C16 C17 1.3854(19) . ? C17 C18 1.5231(16) 2_655 ? C18 C17 1.5231(16) 2_655 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1A C1A C2A 125.2(3) . . ? F1A C1A C6A 114.8(3) . . ? C2A C1A C6A 120.0 . . ? C1A C2A C3A 120.0 . . ? F3A C3A C2A 120.73(12) . . ? F3A C3A C4A 119.26(13) . . ? C2A C3A C4A 120.0 . . ? F4A C4A C5A 122.89(19) . . ? F4A C4A C3A 117.08(19) . . ? C5A C4A C3A 120.0 . . ? C4A C5A C6A 120.0 . . ? C4A C5A F5A 108.7 . . ? C6A C5A F5A 131.2 . . ? C5A C6A C1A 120.0 . . ? F1B C1B C2B 124.3 . . ? F1B C1B C6B 115.7 . . ? C2B C1B C6B 120.0 . . ? C1B C2B C3B 120.0 . . ? F3B C3B C2B 124.1 . . ? F3B C3B C4B 115.9 . . ? C2B C3B C4B 120.0 . . ? F4B C4B C5B 128.9 . . ? F4B C4B C3B 111.1 . . ? C5B C4B C3B 120.0 . . ? F5B C5B C6B 117.5 . . ? F5B C5B C4B 122.5 . . ? C6B C5B C4B 120.0 . . ? C5B C6B C1B 120.0 . . ? C11 C8 C9 108.7(2) . . ? C11 C8 C10 108.3(2) . . ? C9 C8 C10 106.9(2) . . ? C11 C8 C4 111.8(2) . . ? C9 C8 C4 115.47(19) . . ? C10 C8 C4 105.28(19) . . ? C10K C8K C11K 110.3(2) . . ? C10K C8K C4 112.4(2) . . ? C11K C8K C4 115.1(2) . . ? C10K C8K C9K 109.0(3) . . ? C11K C8K C9K 108.3(2) . . ? C4 C8K C9K 101.0(2) . . ? C22 C19 C20 110.2(2) . . ? C22 C19 C21 108.8(3) . . ? C20 C19 C21 108.5(2) . . ? C22 C19 C15 111.9(2) . . ? C20 C19 C15 115.5(2) . . ? C21 C19 C15 101.3(2) . . ? C20K C19K C21K 108.8(2) . . ? C20K C19K C15 111.8(2) . . ? C21K C19K C15 115.75(19) . . ? C20K C19K C22K 107.8(2) . . ? C21K C19K C22K 106.8(2) . . ? C15 C19K C22K 105.4(2) . . ? O1 C1 C2 120.72(10) . . ? O1 C1 C6 118.04(10) . . ? C2 C1 C6 121.25(11) . . ? C3 C2 C1 118.28(11) . . ? C3 C2 C18 119.82(11) . . ? C1 C2 C18 121.88(11) . . ? C2 C3 C4 122.84(12) . . ? C3 C4 C5 116.77(13) . . ? C3 C4 C8K 121.75(15) . . ? C5 C4 C8K 120.17(15) . . ? C3 C4 C8 119.56(14) . . ? C5 C4 C8 122.07(14) . . ? C8K C4 C8 23.41(13) . . ? C6 C5 C4 122.69(12) . . ? C5 C6 C1 118.16(11) . . ? C5 C6 C7 120.08(11) . . ? C1 C6 C7 121.74(11) . . ? C13 C7 C6 112.38(10) . . ? O2 C12 C17 118.18(10) . . ? O2 C12 C13 120.59(10) . . ? C17 C12 C13 121.23(11) . . ? C14 C13 C12 118.19(11) . . ? C14 C13 C7 119.96(11) . . ? C12 C13 C7 121.84(11) . . ? C13 C14 C15 122.94(12) . . ? C16 C15 C14 116.65(13) . . ? C16 C15 C19K 122.00(14) . . ? C14 C15 C19K 119.74(14) . . ? C16 C15 C19 120.38(15) . . ? C14 C15 C19 121.83(15) . . ? C19K C15 C19 22.64(13) . . ? C17 C16 C15 122.75(12) . . ? C16 C17 C12 118.22(11) . . ? C16 C17 C18 120.00(11) . 2_655 ? C12 C17 C18 121.76(11) . 2_655 ? C2 C18 C17 112.51(10) . 2_655 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.81 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.352 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.039 #===END data_p2c_b _database_code_depnum_ccdc_archive 'CCDC 237579' _audit_creation_method SHELXL-97 _chemical_name_systematic ; p-tert-butyl-calix[4]arene*fluorobenzene ; _chemical_name_common p-tert-butyl-calix(4)arene*fluorobenzene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H30.50 F0.50 O2' _chemical_formula_weight 372.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 18.0102(8) _cell_length_b 13.1981(6) _cell_length_c 18.0381(8) _cell_angle_alpha 90.00 _cell_angle_beta 89.9750(10) _cell_angle_gamma 90.00 _cell_volume 4287.7(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9742 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CD Bruker Smart 1000' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 50031 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0513 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 28.75 _reflns_number_total 11349 _reflns_number_gt 6861 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0920P)^2^+0.7498P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11349 _refine_ls_number_parameters 616 _refine_ls_number_restraints 120 _refine_ls_R_factor_all 0.1134 _refine_ls_R_factor_gt 0.0644 _refine_ls_wR_factor_ref 0.1894 _refine_ls_wR_factor_gt 0.1572 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.125 _refine_ls_shift/su_mean 0.008 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.03266(3) 0.45994(4) 0.15178(3) 0.03325(17) Uani 1 1 d . A 1 O2 O 0.09981(3) 0.45740(4) 0.28359(3) 0.03432(17) Uani 1 1 d . A 1 O3 O 0.53437(3) 0.55656(4) 0.14948(3) 0.03373(17) Uani 1 1 d . B 1 O4 O 0.40162(3) 0.55383(4) 0.21540(3) 0.03410(17) Uani 1 1 d . B 1 C1 C 0.04465(5) 0.54690(6) 0.11010(4) 0.0280(2) Uani 1 1 d . A 1 C2 C 0.11542(5) 0.58804(6) 0.10888(4) 0.0280(2) Uani 1 1 d . A 1 C3 C 0.12859(5) 0.67177(7) 0.06363(5) 0.0310(2) Uani 1 1 d . A 1 H3A H 0.1771 0.7000 0.0622 0.037 Uiso 1 1 calc R A 1 C5 C 0.00249(5) 0.67266(6) 0.02446(5) 0.0305(2) Uani 1 1 d . A 1 H5 H -0.0365 0.7015 -0.0040 0.037 Uiso 1 1 calc R A 1 C6 C -0.01302(5) 0.58923(6) 0.06861(4) 0.0281(2) Uani 1 1 d . . 1 C8 C 0.17739(5) 0.54560(6) 0.15740(4) 0.0285(2) Uani 1 1 d . A 1 H8A H 0.1717 0.4711 0.1609 0.034 Uiso 1 1 calc R A 1 H8B H 0.2258 0.5597 0.1335 0.034 Uiso 1 1 calc R A 1 C21 C 0.13846(5) 0.54693(6) 0.29374(5) 0.0275(2) Uani 1 1 d . A 1 C22 C 0.13734(5) 0.59085(6) 0.36462(5) 0.0280(2) Uani 1 1 d . A 1 C23 C 0.17859(5) 0.67813(7) 0.37547(5) 0.0308(2) Uani 1 1 d . A 1 H23 H 0.1781 0.7087 0.4231 0.037 Uiso 1 1 calc R A 1 C25 C 0.21867(5) 0.67773(7) 0.24986(5) 0.0303(2) Uani 1 1 d . A 1 H25 H 0.2461 0.7077 0.2106 0.036 Uiso 1 1 calc R A 1 C26 C 0.17784(5) 0.59004(6) 0.23524(5) 0.0274(2) Uani 1 1 d . A 1 C28 C 0.09182(5) 0.54704(7) 0.42827(5) 0.0313(2) Uani 1 1 d . . 1 H28A H 0.1172 0.5621 0.4757 0.038 Uiso 1 1 calc R . 1 H28B H 0.0894 0.4725 0.4228 0.038 Uiso 1 1 calc R . 1 C41 C 0.54526(5) 0.46562(6) 0.11232(4) 0.0283(2) Uani 1 1 d . B 1 C42 C 0.61544(5) 0.42204(6) 0.11403(5) 0.0279(2) Uani 1 1 d . B 1 C43 C 0.62661(5) 0.33211(7) 0.07535(5) 0.0316(2) Uani 1 1 d . B 1 H43 H 0.6744 0.3017 0.0766 0.038 Uiso 1 1 calc R B 1 C45 C 0.50152(5) 0.33124(7) 0.03453(5) 0.0308(2) Uani 1 1 d . B 1 H45 H 0.4624 0.3007 0.0072 0.037 Uiso 1 1 calc R B 1 C46 C 0.48712(5) 0.42065(7) 0.07253(4) 0.0285(2) Uani 1 1 d . B 1 C48 C 0.67788(5) 0.46723(7) 0.15963(5) 0.0294(2) Uani 1 1 d . . 1 H48A H 0.6714 0.5416 0.1621 0.035 Uiso 1 1 calc R . 1 H48B H 0.7258 0.4534 0.1347 0.035 Uiso 1 1 calc R . 1 C61 C 0.36053(5) 0.46628(6) 0.20407(5) 0.0268(2) Uani 1 1 d . B 1 C62 C 0.36065(5) 0.42352(6) 0.13311(5) 0.0273(2) Uani 1 1 d . B 1 C63 C 0.31688(5) 0.33834(6) 0.12092(5) 0.0297(2) Uani 1 1 d . B 1 H63 H 0.3163 0.3091 0.0728 0.036 Uiso 1 1 calc R B 1 C65 C 0.27671(5) 0.33910(7) 0.24673(5) 0.0312(2) Uani 1 1 d . B 1 H65 H 0.2483 0.3101 0.2857 0.037 Uiso 1 1 calc R B 1 C66 C 0.31949(5) 0.42462(6) 0.26181(5) 0.0274(2) Uani 1 1 d . . 1 C68 C 0.40925(5) 0.46505(7) 0.07134(5) 0.0298(2) Uani 1 1 d . B 1 H68A H 0.4125 0.5396 0.0762 0.036 Uiso 1 1 calc R B 1 H68B H 0.3858 0.4498 0.0230 0.036 Uiso 1 1 calc R B 1 C4 C 0.07275(5) 0.71563(7) 0.02028(5) 0.0332(2) Uani 1 1 d . A 1 C7 C 0.09010(10) 0.80335(17) -0.02345(10) 0.0374(5) Uani 0.4846(10) 1 d P C 2 C9 C 0.02722(14) 0.8456(2) -0.07032(15) 0.0705(8) Uani 0.4846(10) 1 d P C 2 H9A H -0.0129 0.8692 -0.0379 0.106 Uiso 0.4846(10) 1 calc PR C 2 H9B H 0.0083 0.7925 -0.1033 0.106 Uiso 0.4846(10) 1 calc PR C 2 H9C H 0.0456 0.9025 -0.1001 0.106 Uiso 0.4846(10) 1 calc PR C 2 C10 C 0.15331(13) 0.77406(19) -0.08410(12) 0.0524(7) Uani 0.4846(10) 1 d P C 2 H10A H 0.1977 0.7492 -0.0585 0.079 Uiso 0.4846(10) 1 calc PR C 2 H10B H 0.1661 0.8342 -0.1133 0.079 Uiso 0.4846(10) 1 calc PR C 2 H10C H 0.1343 0.7211 -0.1171 0.079 Uiso 0.4846(10) 1 calc PR C 2 C11 C 0.12545(14) 0.89692(16) 0.01902(13) 0.0534(7) Uani 0.4846(10) 1 d P C 2 H11A H 0.1692 0.8744 0.0468 0.080 Uiso 0.4846(10) 1 calc PR C 2 H11B H 0.0888 0.9254 0.0534 0.080 Uiso 0.4846(10) 1 calc PR C 2 H11C H 0.1402 0.9488 -0.0169 0.080 Uiso 0.4846(10) 1 calc PR C 2 C24 C 0.22093(5) 0.72333(7) 0.31955(5) 0.0326(2) Uani 1 1 d . A 1 C27 C 0.26769(6) 0.81774(8) 0.33680(5) 0.0428(3) Uani 1 1 d . A 1 C29 C 0.30668(7) 0.85843(10) 0.26785(7) 0.0673(4) Uani 1 1 d . A 1 H29A H 0.3362 0.9181 0.2811 0.101 Uiso 1 1 calc R A 1 H29B H 0.2695 0.8773 0.2306 0.101 Uiso 1 1 calc R A 1 H29C H 0.3394 0.8060 0.2475 0.101 Uiso 1 1 calc R A 1 C30 C 0.32621(6) 0.79012(10) 0.39420(7) 0.0611(4) Uani 1 1 d . A 1 H30A H 0.3563 0.8500 0.4057 0.092 Uiso 1 1 calc R A 1 H30B H 0.3583 0.7365 0.3744 0.092 Uiso 1 1 calc R A 1 H30C H 0.3018 0.7661 0.4394 0.092 Uiso 1 1 calc R A 1 C31 C 0.21740(7) 0.90138(8) 0.36851(7) 0.0585(4) Uani 1 1 d . A 1 H31A H 0.2474 0.9613 0.3799 0.088 Uiso 1 1 calc R A 1 H31B H 0.1934 0.8769 0.4139 0.088 Uiso 1 1 calc R A 1 H31C H 0.1794 0.9192 0.3319 0.088 Uiso 1 1 calc R A 1 C44 C 0.57031(5) 0.28470(7) 0.03469(5) 0.0328(2) Uani 1 1 d . B 1 C47 C 0.58681(5) 0.18702(8) -0.00801(6) 0.0445(3) Uani 1 1 d . B 1 C49 C 0.64354(7) 0.20911(10) -0.06878(7) 0.0658(4) Uani 1 1 d . B 1 H49A H 0.6886 0.2373 -0.0465 0.099 Uiso 1 1 calc R B 1 H49B H 0.6226 0.2580 -0.1039 0.099 Uiso 1 1 calc R B 1 H49C H 0.6557 0.1462 -0.0949 0.099 Uiso 1 1 calc R B 1 C50 C 0.62106(7) 0.10687(9) 0.04669(8) 0.0633(4) Uani 1 1 d . B 1 H50A H 0.6660 0.1348 0.0694 0.095 Uiso 1 1 calc R B 1 H50B H 0.6336 0.0451 0.0193 0.095 Uiso 1 1 calc R B 1 H50C H 0.5849 0.0907 0.0855 0.095 Uiso 1 1 calc R B 1 C51 C 0.51718(7) 0.13941(10) -0.03987(8) 0.0812(4) Uani 1 1 d . B 1 H51A H 0.5302 0.0766 -0.0658 0.122 Uiso 1 1 calc R B 1 H51B H 0.4939 0.1867 -0.0748 0.122 Uiso 1 1 calc R B 1 H51C H 0.4824 0.1242 0.0004 0.122 Uiso 1 1 calc R B 1 C64 C 0.27394(5) 0.29413(7) 0.17634(5) 0.0322(2) Uani 1 1 d . B 1 C67 C 0.22267(7) 0.20343(9) 0.16639(7) 0.0365(3) Uani 0.7682(10) 1 d P B 1 C69 C 0.23180(10) 0.15754(12) 0.08823(8) 0.0638(5) Uani 0.7682(10) 1 d P B 1 H69A H 0.2210 0.2094 0.0509 0.096 Uiso 0.7682(10) 1 calc PR B 1 H69B H 0.1973 0.1007 0.0823 0.096 Uiso 0.7682(10) 1 calc PR B 1 H69C H 0.2829 0.1334 0.0819 0.096 Uiso 0.7682(10) 1 calc PR B 1 C70 C 0.24061(9) 0.12114(10) 0.22274(9) 0.0573(5) Uani 0.7682(10) 1 d P B 1 H70A H 0.2348 0.1483 0.2730 0.086 Uiso 0.7682(10) 1 calc PR B 1 H70B H 0.2919 0.0983 0.2157 0.086 Uiso 0.7682(10) 1 calc PR B 1 H70C H 0.2067 0.0638 0.2159 0.086 Uiso 0.7682(10) 1 calc PR B 1 C71 C 0.14147(7) 0.23435(11) 0.17489(9) 0.0509(4) Uani 0.7682(10) 1 d P B 1 H71A H 0.1337 0.2638 0.2242 0.076 Uiso 0.7682(10) 1 calc PR B 1 H71B H 0.1097 0.1746 0.1691 0.076 Uiso 0.7682(10) 1 calc PR B 1 H71C H 0.1288 0.2846 0.1369 0.076 Uiso 0.7682(10) 1 calc PR B 1 C7B C 0.08795(12) 0.80673(13) -0.03833(11) 0.0370(5) Uani 0.5154(10) 1 d P A 1 C9B C 0.02691(14) 0.89020(16) -0.01621(14) 0.0593(7) Uani 0.5154(10) 1 d P A 1 H9B1 H -0.0229 0.8615 -0.0224 0.089 Uiso 0.5154(10) 1 calc PR C 1 H9B2 H 0.0324 0.9496 -0.0483 0.089 Uiso 0.5154(10) 1 calc PR C 1 H9B3 H 0.0340 0.9104 0.0356 0.089 Uiso 0.5154(10) 1 calc PR C 1 C10B C 0.07413(14) 0.76943(18) -0.11563(12) 0.0594(7) Uani 0.5154(10) 1 d P A 1 H10D H 0.1091 0.7148 -0.1272 0.089 Uiso 0.5154(10) 1 calc PR C 1 H10E H 0.0811 0.8253 -0.1508 0.089 Uiso 0.5154(10) 1 calc PR C 1 H10F H 0.0232 0.7439 -0.1194 0.089 Uiso 0.5154(10) 1 calc PR C 1 C11B C 0.16186(14) 0.84791(18) -0.02581(16) 0.0762(8) Uani 0.5154(10) 1 d P A 1 H11D H 0.1991 0.7959 -0.0368 0.114 Uiso 0.5154(10) 1 calc PR C 1 H11E H 0.1665 0.8691 0.0261 0.114 Uiso 0.5154(10) 1 calc PR C 1 H11F H 0.1697 0.9065 -0.0583 0.114 Uiso 0.5154(10) 1 calc PR C 1 C67B C 0.2300(3) 0.1933(3) 0.1507(2) 0.0365(3) Uani 0.2318(10) 1 d P B 2 C69B C 0.2771(3) 0.1161(3) 0.1196(3) 0.0563(15) Uani 0.2318(10) 1 d P B 2 H69D H 0.3133 0.0942 0.1569 0.085 Uiso 0.2318(10) 1 calc PR B 2 H69E H 0.3033 0.1434 0.0764 0.085 Uiso 0.2318(10) 1 calc PR B 2 H69F H 0.2467 0.0581 0.1045 0.085 Uiso 0.2318(10) 1 calc PR B 2 C70B C 0.1936(3) 0.1553(4) 0.2260(3) 0.0660(14) Uani 0.2318(10) 1 d P B 2 H70D H 0.1630 0.2096 0.2471 0.099 Uiso 0.2318(10) 1 calc PR B 2 H70E H 0.2328 0.1371 0.2612 0.099 Uiso 0.2318(10) 1 calc PR B 2 H70F H 0.1624 0.0959 0.2162 0.099 Uiso 0.2318(10) 1 calc PR B 2 C71B C 0.16981(3) 0.23397(14) 0.09950(3) 0.0647(16) Uani 0.2318(10) 1 d P B 2 H71D H 0.1407 0.2855 0.1257 0.097 Uiso 0.2318(10) 1 calc PR B 2 H71E H 0.1371 0.1784 0.0843 0.097 Uiso 0.2318(10) 1 calc PR B 2 H71F H 0.1928 0.2642 0.0555 0.097 Uiso 0.2318(10) 1 calc PR B 2 H2 H 0.0887 0.4499 0.2501 0.100 Uiso 1 1 d R B 1 H1 H -0.0100 0.4503 0.1681 0.100 Uiso 1 1 d R B 1 H3 H 0.4911 0.5564 0.1714 0.100 Uiso 1 1 d R B 1 H4 H 0.4119 0.5520 0.2597 0.100 Uiso 1 1 d R B 1 F200 F 0.88599(3) 0.93800(14) 0.33451(3) 0.2443(11) Uani 0.4509(6) 1 d PRDU D -3 C201 C 0.94246(2) 0.91037(7) 0.29319(3) 0.0653(8) Uani 0.4509(6) 1 d PGDU D -3 C202 C 0.96247(2) 0.80887(7) 0.28834(3) 0.0563(7) Uani 0.4509(6) 1 d PGDU D -3 H202 H 0.9352 0.7592 0.3150 0.068 Uiso 0.4509(6) 1 calc PR D -3 C203 C 1.02234(2) 0.78010(7) 0.24448(3) 0.0446(7) Uani 0.4509(6) 1 d PGDU D -3 H203 H 1.0360 0.7107 0.2412 0.053 Uiso 0.4509(6) 1 calc PR D -3 C204 C 1.06220(3) 0.85284(7) 0.20546(3) 0.0590(8) Uani 0.4509(6) 1 d PGDU D -3 H204 H 1.1031 0.8332 0.1755 0.071 Uiso 0.4509(6) 1 calc PR D -3 C205 C 1.04220(3) 0.95434(7) 0.21030(3) 0.0648(9) Uani 0.4509(6) 1 d PGDU D -3 H205 H 1.0694 1.0041 0.1836 0.078 Uiso 0.4509(6) 1 calc PR D -3 C206 C 0.98233(2) 0.98311(7) 0.25417(3) 0.0618(10) Uani 0.4509(6) 1 d PGDU D -3 H206 H 0.9687 1.0525 0.2575 0.074 Uiso 0.4509(6) 1 calc PR D -3 F300 F 0.58301(4) 0.08143(7) 0.36704(6) 0.1836(9) Uani 0.4655(6) 1 d PGDU E -4 C301 C 0.54103(2) 0.10239(6) 0.30839(3) 0.0574(7) Uani 0.4655(6) 1 d PGDU E -4 C302 C 0.50501(2) 0.02496(7) 0.27053(3) 0.0500(7) Uani 0.4655(6) 1 d PGDU E -4 H302 H 0.5103 -0.0432 0.2865 0.060 Uiso 0.4655(6) 1 calc PR E -4 C303 C 0.46119(3) 0.04731(7) 0.20925(3) 0.0572(8) Uani 0.4655(6) 1 d PGDU E -4 H303 H 0.4366 -0.0056 0.1834 0.069 Uiso 0.4655(6) 1 calc PR E -4 C304 C 0.45339(3) 0.14708(7) 0.18584(3) 0.0795(10) Uani 0.4655(6) 1 d PGDU E -4 H304 H 0.4234 0.1624 0.1440 0.095 Uiso 0.4655(6) 1 calc PR E -4 C305 C 0.48942(2) 0.22451(7) 0.22371(3) 0.1037(14) Uani 0.4655(6) 1 d PGDU E -4 H305 H 0.4841 0.2927 0.2077 0.124 Uiso 0.4655(6) 1 calc PR E -4 C306 C 0.53323(2) 0.20217(6) 0.28498(3) 0.0898(10) Uani 0.4655(6) 1 d PGDU E -4 H306 H 0.5579 0.2551 0.3109 0.108 Uiso 0.4655(6) 1 calc PR E -4 F210 F 1.05950(4) 0.88380(8) 0.38312(7) 0.069(4) Uiso 0.0491(6) 1 d PGD D -5 C211 C 1.02903(2) 0.88112(9) 0.31617(3) 0.0269(14) Uiso 0.0491(6) 1 d PGD D -5 C212 C 0.99494(2) 0.96674(9) 0.28693(3) 0.0269(14) Uiso 0.0491(6) 1 d PGD D -5 H212 H 0.9934 1.0277 0.3149 0.032 Uiso 0.0491(6) 1 calc PR D -5 C213 C 0.96318(2) 0.96319(9) 0.21676(3) 0.0269(14) Uiso 0.0491(6) 1 d PGD D -5 H213 H 0.9399 1.0217 0.1968 0.032 Uiso 0.0491(6) 1 calc PR D -5 C214 C 0.96551(2) 0.87401(9) 0.17582(3) 0.0269(14) Uiso 0.0491(6) 1 d PGD D -5 H214 H 0.9438 0.8716 0.1279 0.032 Uiso 0.0491(6) 1 calc PR D -5 C215 C 0.99960(2) 0.78840(9) 0.20506(3) 0.0269(14) Uiso 0.0491(6) 1 d PGD D -5 H215 H 1.0012 0.7275 0.1771 0.032 Uiso 0.0491(6) 1 calc PR D -5 C216 C 1.03136(2) 0.79195(9) 0.27523(3) 0.0269(14) Uiso 0.0491(6) 1 d PGD D -5 H216 H 1.0547 0.7334 0.2952 0.032 Uiso 0.0491(6) 1 calc PR D -5 F310 F 0.50268(4) -0.08363(9) 0.25915(5) 0.056(3) Uiso 0.0345(6) 1 d PRD E -6 C311 C 0.49236(4) 0.01612(13) 0.25751(5) 0.042(3) Uiso 0.0345(6) 1 d PGD E -6 C312 C 0.4429(2) 0.06125(14) 0.3066(2) 0.042(3) Uiso 0.0345(6) 1 d PGD E -6 H312 H 0.4165 0.0208 0.3413 0.051 Uiso 0.0345(6) 1 calc PR E -6 C313 C 0.4321(2) 0.16551(14) 0.3049(3) 0.042(3) Uiso 0.0345(6) 1 d PGD E -6 H313 H 0.3983 0.1963 0.3385 0.051 Uiso 0.0345(6) 1 calc PR E -6 C314 C 0.47075(9) 0.22463(13) 0.25416(13) 0.042(3) Uiso 0.0345(6) 1 d PGD E -6 H314 H 0.4634 0.2959 0.2530 0.051 Uiso 0.0345(6) 1 calc PR E -6 C315 C 0.5202(2) 0.17951(14) 0.20505(14) 0.042(3) Uiso 0.0345(6) 1 d PGD E -6 H315 H 0.5466 0.2199 0.1703 0.051 Uiso 0.0345(6) 1 calc PR E -6 C316 C 0.5310(2) 0.07525(14) 0.20673(17) 0.042(3) Uiso 0.0345(6) 1 d PGD E -6 H316 H 0.5648 0.0444 0.1732 0.051 Uiso 0.0345(6) 1 calc PR E -6 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0335(3) 0.0336(3) 0.0326(3) 0.0010(3) -0.0002(3) -0.0004(3) O2 0.0369(3) 0.0316(3) 0.0345(3) -0.0018(3) -0.0018(3) -0.0038(3) O3 0.0359(3) 0.0312(3) 0.0341(3) 0.0011(3) -0.0001(3) -0.0005(3) O4 0.0374(3) 0.0299(3) 0.0350(3) -0.0011(3) -0.0028(3) -0.0024(3) C1 0.0321(4) 0.0308(4) 0.0211(4) -0.0026(3) 0.0022(3) 0.0013(4) C2 0.0255(4) 0.0331(4) 0.0254(4) -0.0056(3) -0.0006(3) 0.0044(3) C3 0.0265(4) 0.0373(4) 0.0293(4) -0.0017(4) 0.0014(3) 0.0016(4) C5 0.0282(4) 0.0351(4) 0.0282(4) 0.0007(4) -0.0006(4) 0.0055(4) C6 0.0253(4) 0.0357(4) 0.0234(4) -0.0046(3) 0.0024(3) 0.0023(4) C8 0.0269(4) 0.0338(4) 0.0250(4) -0.0035(3) 0.0010(3) 0.0037(4) C21 0.0241(4) 0.0278(4) 0.0305(4) 0.0012(3) -0.0021(3) 0.0038(3) C22 0.0207(4) 0.0352(4) 0.0282(4) 0.0022(4) -0.0017(3) 0.0049(3) C23 0.0279(4) 0.0387(4) 0.0256(4) -0.0060(4) -0.0017(3) 0.0006(4) C25 0.0273(4) 0.0371(4) 0.0265(4) 0.0003(4) 0.0026(3) 0.0012(4) C26 0.0234(4) 0.0315(4) 0.0273(4) -0.0026(3) -0.0006(3) 0.0059(3) C28 0.0276(4) 0.0406(5) 0.0257(4) 0.0016(4) -0.0009(4) 0.0019(4) C41 0.0331(4) 0.0289(4) 0.0230(4) 0.0031(3) 0.0017(4) -0.0009(4) C42 0.0253(4) 0.0323(4) 0.0262(4) 0.0057(3) -0.0017(3) -0.0038(3) C43 0.0269(4) 0.0390(5) 0.0291(4) 0.0031(4) -0.0018(4) 0.0001(4) C45 0.0265(4) 0.0362(4) 0.0295(4) 0.0017(4) -0.0026(4) -0.0029(4) C46 0.0257(4) 0.0375(4) 0.0224(4) 0.0083(3) 0.0019(3) 0.0006(4) C48 0.0223(4) 0.0384(4) 0.0275(4) 0.0035(4) -0.0007(3) -0.0043(4) C61 0.0269(4) 0.0260(4) 0.0273(4) 0.0022(3) -0.0040(3) 0.0060(3) C62 0.0249(4) 0.0294(4) 0.0274(4) 0.0039(3) -0.0028(3) 0.0053(3) C63 0.0325(4) 0.0312(4) 0.0255(4) -0.0025(4) -0.0035(4) 0.0021(4) C65 0.0271(4) 0.0380(4) 0.0285(4) 0.0035(4) -0.0014(4) -0.0016(4) C66 0.0254(4) 0.0317(4) 0.0252(4) -0.0001(4) -0.0010(3) 0.0056(4) C68 0.0279(4) 0.0345(4) 0.0269(4) 0.0053(4) -0.0031(4) 0.0005(4) C4 0.0313(4) 0.0344(4) 0.0340(4) 0.0023(4) -0.0018(4) 0.0007(4) C7 0.0324(9) 0.0613(12) 0.0186(8) 0.0087(8) -0.0060(7) 0.0041(9) C9 0.0507(14) 0.0743(14) 0.0866(16) 0.0527(12) -0.0031(12) -0.0049(12) C10 0.0520(12) 0.0684(14) 0.0369(11) 0.0101(11) 0.0026(10) -0.0115(12) C11 0.0713(15) 0.0356(10) 0.0535(13) 0.0039(10) 0.0007(12) -0.0141(11) C24 0.0303(4) 0.0353(4) 0.0323(4) -0.0015(4) -0.0005(4) -0.0011(4) C27 0.0468(5) 0.0431(5) 0.0383(5) -0.0077(4) 0.0032(4) -0.0128(5) C29 0.0839(8) 0.0679(7) 0.0499(6) -0.0096(6) 0.0198(6) -0.0376(6) C30 0.0433(6) 0.0769(7) 0.0631(7) -0.0193(6) -0.0088(5) -0.0163(6) C31 0.0693(7) 0.0464(6) 0.0599(7) -0.0091(5) 0.0061(6) -0.0111(6) C44 0.0316(4) 0.0360(4) 0.0308(4) -0.0032(4) -0.0009(4) 0.0032(4) C47 0.0303(5) 0.0479(5) 0.0555(6) -0.0199(5) -0.0030(4) 0.0031(4) C49 0.0697(8) 0.0750(8) 0.0527(6) -0.0202(6) 0.0039(6) 0.0117(7) C50 0.0553(7) 0.0460(6) 0.0885(9) -0.0050(6) -0.0011(7) 0.0078(6) C51 0.0528(7) 0.0711(7) 0.1197(9) -0.0577(7) -0.0187(7) 0.0092(6) C64 0.0325(4) 0.0325(4) 0.0315(4) 0.0043(4) -0.0054(4) -0.0004(4) C67 0.0461(6) 0.0338(5) 0.0295(5) -0.0044(4) 0.0006(5) -0.0053(5) C69 0.0880(11) 0.0555(8) 0.0480(8) -0.0117(7) 0.0089(8) -0.0304(8) C70 0.0712(10) 0.0387(7) 0.0621(9) 0.0126(7) -0.0039(8) -0.0106(7) C71 0.0438(7) 0.0430(7) 0.0658(9) 0.0009(7) -0.0052(7) -0.0133(6) C7B 0.0535(11) 0.0243(8) 0.0331(9) 0.0164(7) 0.0058(8) -0.0071(8) C9B 0.0782(16) 0.0379(10) 0.0619(13) 0.0101(10) 0.0117(12) 0.0098(11) C10B 0.0735(15) 0.0598(12) 0.0449(11) 0.0219(10) 0.0115(11) 0.0010(12) C11B 0.0640(14) 0.0582(12) 0.1065(18) 0.0431(12) -0.0217(13) -0.0280(11) C67B 0.0461(6) 0.0338(5) 0.0295(5) -0.0044(4) 0.0006(5) -0.0053(5) C69B 0.076(3) 0.033(2) 0.061(3) -0.005(2) -0.010(3) -0.009(2) C70B 0.085(3) 0.074(3) 0.039(2) -0.021(2) 0.027(2) -0.061(2) C71B 0.040(2) 0.079(3) 0.076(3) -0.020(3) -0.027(2) -0.023(2) F200 0.2136(16) 0.316(2) 0.204(2) 0.135(2) 0.1409(15) 0.2053(15) C201 0.0826(16) 0.0437(11) 0.0694(15) 0.0304(10) 0.0215(13) 0.0439(11) C202 0.0431(11) 0.0589(13) 0.0669(14) 0.0204(12) 0.0361(10) 0.0168(11) C203 0.0550(17) 0.0397(9) 0.0390(11) 0.0001(11) 0.0185(12) 0.0070(8) C204 0.0487(13) 0.0632(15) 0.0650(14) 0.0268(12) 0.0264(11) -0.0041(12) C205 0.0744(18) 0.0380(13) 0.0820(19) -0.0048(13) 0.0194(15) -0.0028(13) C206 0.087(3) 0.0387(9) 0.0598(13) 0.0062(18) 0.0070(18) 0.0106(12) F300 0.1194(14) 0.270(2) 0.1614(14) 0.1563(13) -0.0813(11) -0.0867(15) C301 0.0524(12) 0.0884(16) 0.0314(10) 0.0066(11) -0.0211(9) -0.0402(11) C302 0.0553(13) 0.0464(9) 0.0484(17) 0.0140(8) -0.0021(14) 0.0130(14) C303 0.0507(13) 0.0851(18) 0.0357(11) 0.0004(12) -0.0157(10) -0.0189(13) C304 0.0417(13) 0.0698(15) 0.127(2) 0.0524(15) 0.0001(15) 0.0166(12) C305 0.116(2) 0.0893(18) 0.106(3) 0.0148(17) 0.050(2) 0.006(3) C306 0.148(3) 0.0451(11) 0.0764(18) -0.0334(11) 0.0460(16) -0.0612(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.3888(10) . ? O2 C21 1.3836(10) . ? O3 C41 1.3887(10) . ? O4 C61 1.3873(10) . ? C1 C2 1.3857(12) . ? C1 C6 1.3969(12) . ? C2 C3 1.3941(12) . ? C2 C8 1.5252(12) . ? C3 C4 1.3994(12) . ? C5 C6 1.3873(12) . ? C5 C4 1.3887(12) . ? C6 C28 1.5255(12) 2 ? C8 C26 1.5217(12) . ? C21 C26 1.3926(12) . ? C21 C22 1.4040(12) . ? C22 C23 1.3846(12) . ? C22 C28 1.5244(12) . ? C23 C24 1.3980(12) . ? C25 C26 1.3965(12) . ? C25 C24 1.3944(12) . ? C28 C6 1.5255(12) 2 ? C41 C42 1.3889(12) . ? C41 C46 1.4016(12) . ? C42 C43 1.3914(12) . ? C42 C48 1.5159(12) . ? C43 C44 1.3993(12) . ? C45 C44 1.3828(12) . ? C45 C46 1.3891(12) . ? C46 C68 1.5201(12) . ? C48 C66 1.5254(12) 2_655 ? C61 C66 1.3901(12) . ? C61 C62 1.3988(12) . ? C62 C63 1.3906(12) . ? C62 C68 1.5191(12) . ? C63 C64 1.3919(12) . ? C65 C66 1.3935(12) . ? C65 C64 1.4024(12) . ? C66 C48 1.5254(12) 2_655 ? C4 C7B 1.624(2) . ? C7 C9 1.520(3) . ? C7 C11 1.587(3) . ? C7 C10 1.625(3) . ? C24 C27 1.5359(13) . ? C27 C30 1.5219(16) . ? C27 C29 1.5257(16) . ? C27 C31 1.5380(16) . ? C44 C47 1.5309(14) . ? C47 C51 1.5161(16) . ? C47 C49 1.5261(16) . ? C47 C50 1.5727(16) . ? C64 C67 1.5224(15) . ? C67 C70 1.5224(19) . ? C67 C71 1.5261(19) . ? C67 C69 1.5431(19) . ? C7B C11B 1.456(3) . ? C7B C10B 1.500(3) . ? C7B C9B 1.607(3) . ? C67B C69B 1.439(7) . ? C67B C71B 1.523(5) . ? C67B C70B 1.589(6) . ? F200 C201 1.3124 . ? C201 C202 1.3900 . ? C201 C206 1.3900 . ? C202 C203 1.3900 . ? C203 C204 1.3900 . ? C204 C205 1.3900 . ? C205 C206 1.3900 . ? F300 C301 1.3297(11) . ? C301 C302 1.3900 . ? C301 C306 1.3900 . ? C302 C303 1.3900 . ? C303 C304 1.3900 . ? C304 C305 1.3900 . ? C305 C306 1.3900 . ? F210 C211 1.3274(12) . ? C211 C212 1.3900 . ? C211 C216 1.3900 . ? C212 C213 1.3900 . ? C213 C214 1.3900 . ? C214 C215 1.3900 . ? C215 C216 1.3900 . ? F310 C311 1.330(2) . ? C311 C312 1.3900 . ? C311 C316 1.3900 . ? C312 C313 1.3900 . ? C313 C314 1.3900 . ? C314 C315 1.3900 . ? C315 C316 1.3900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 O1 118.36(7) . . ? C2 C1 C6 121.26(8) . . ? O1 C1 C6 120.34(7) . . ? C1 C2 C3 118.43(8) . . ? C1 C2 C8 121.36(7) . . ? C3 C2 C8 120.19(7) . . ? C2 C3 C4 122.20(8) . . ? C6 C5 C4 122.58(8) . . ? C5 C6 C1 118.38(8) . . ? C5 C6 C28 119.87(7) . 2 ? C1 C6 C28 121.74(7) . 2 ? C26 C8 C2 113.08(7) . . ? O2 C21 C26 120.32(7) . . ? O2 C21 C22 117.78(7) . . ? C26 C21 C22 121.89(8) . . ? C23 C22 C21 117.70(8) . . ? C23 C22 C28 119.83(8) . . ? C21 C22 C28 122.46(7) . . ? C22 C23 C24 123.06(8) . . ? C26 C25 C24 122.92(8) . . ? C21 C26 C25 117.63(8) . . ? C21 C26 C8 122.60(7) . . ? C25 C26 C8 119.78(7) . . ? C22 C28 C6 112.91(7) . 2 ? C42 C41 O3 118.40(7) . . ? C42 C41 C46 121.07(8) . . ? O3 C41 C46 120.51(8) . . ? C41 C42 C43 118.26(8) . . ? C41 C42 C48 121.63(7) . . ? C43 C42 C48 120.03(8) . . ? C42 C43 C44 122.66(8) . . ? C44 C45 C46 122.92(8) . . ? C45 C46 C41 118.23(8) . . ? C45 C46 C68 119.51(8) . . ? C41 C46 C68 122.24(8) . . ? C42 C48 C66 112.48(7) . 2_655 ? O4 C61 C66 120.17(7) . . ? O4 C61 C62 118.05(7) . . ? C66 C61 C62 121.77(8) . . ? C63 C62 C61 118.05(8) . . ? C63 C62 C68 120.15(7) . . ? C61 C62 C68 121.75(7) . . ? C62 C63 C64 122.69(8) . . ? C66 C65 C64 122.65(8) . . ? C61 C66 C65 117.90(8) . . ? C61 C66 C48 122.25(8) . 2_655 ? C65 C66 C48 119.82(7) . 2_655 ? C62 C68 C46 112.44(7) . . ? C5 C4 C3 117.12(8) . . ? C5 C4 C7B 119.40(10) . . ? C3 C4 C7B 123.29(10) . . ? C9 C7 C11 106.39(18) . . ? C9 C7 C10 103.59(16) . . ? C11 C7 C10 103.24(17) . . ? C25 C24 C23 116.76(8) . . ? C25 C24 C27 123.30(8) . . ? C23 C24 C27 119.93(8) . . ? C30 C27 C29 108.68(9) . . ? C30 C27 C24 108.87(9) . . ? C29 C27 C24 111.87(8) . . ? C30 C27 C31 109.08(9) . . ? C29 C27 C31 108.74(9) . . ? C24 C27 C31 109.55(9) . . ? C45 C44 C43 116.86(8) . . ? C45 C44 C47 123.15(8) . . ? C43 C44 C47 119.98(8) . . ? C51 C47 C49 111.13(10) . . ? C51 C47 C44 112.29(9) . . ? C49 C47 C44 109.28(9) . . ? C51 C47 C50 106.49(9) . . ? C49 C47 C50 108.45(9) . . ? C44 C47 C50 109.08(9) . . ? C63 C64 C65 116.93(8) . . ? C63 C64 C67 125.57(9) . . ? C65 C64 C67 117.48(8) . . ? C64 C67 C70 110.69(10) . . ? C64 C67 C71 111.05(10) . . ? C70 C67 C71 109.10(11) . . ? C64 C67 C69 110.61(10) . . ? C70 C67 C69 107.91(11) . . ? C71 C67 C69 107.37(12) . . ? C11B C7B C10B 114.8(2) . . ? C11B C7B C9B 109.34(17) . . ? C10B C7B C9B 110.01(18) . . ? C11B C7B C4 109.23(16) . . ? C10B C7B C4 109.53(14) . . ? C9B C7B C4 103.34(14) . . ? C69B C67B C71B 115.6(4) . . ? C69B C67B C70B 110.7(4) . . ? C71B C67B C70B 109.6(3) . . ? F200 C201 C202 120.28(8) . . ? F200 C201 C206 119.72(8) . . ? C202 C201 C206 120.0 . . ? C203 C202 C201 120.0 . . ? C202 C203 C204 120.0 . . ? C205 C204 C203 120.0 . . ? C206 C205 C204 120.0 . . ? C205 C206 C201 120.0 . . ? F300 C301 C302 120.24(5) . . ? F300 C301 C306 119.76(5) . . ? C302 C301 C306 120.0 . . ? C301 C302 C303 120.0 . . ? C304 C303 C302 120.0 . . ? C303 C304 C305 120.0 . . ? C306 C305 C304 120.0 . . ? C305 C306 C301 120.0 . . ? F210 C211 C212 120.42(7) . . ? F210 C211 C216 119.58(7) . . ? C212 C211 C216 120.0 . . ? C211 C212 C213 120.0 . . ? C212 C213 C214 120.0 . . ? C215 C214 C213 120.0 . . ? C214 C215 C216 120.0 . . ? C215 C216 C211 120.0 . . ? F310 C311 C312 119.97(6) . . ? F310 C311 C316 120.03(6) . . ? C312 C311 C316 120.0 . . ? C311 C312 C313 120.0 . . ? C312 C313 C314 120.0 . . ? C313 C314 C315 120.0 . . ? C316 C315 C314 120.0 . . ? C315 C316 C311 120.0 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.75 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.319 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.054 #===END data_koss28 _database_code_depnum_ccdc_archive 'CCDC 237580' _audit_creation_method SHELXL-97 _chemical_name_systematic ; p-tert-butyl-calix[4]arene*fluorobenzene ; _chemical_name_common p-tert-butyl-calix(4)arene*fluorobenzene _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H61 F O4' _chemical_formula_weight 744.99 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M P4/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y+1/2, x, z' 'y, -x+1/2, z' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y-1/2, -x, -z' '-y, x-1/2, -z' _cell_length_a 12.8581(2) _cell_length_b 12.8581(2) _cell_length_c 13.2833(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2196.14(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.127 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9699 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD Bruker Smart 1000' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15002 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0146 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.70 _reflns_number_total 2833 _reflns_number_gt 2170 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0844P)^2^+0.3774P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.006(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2833 _refine_ls_number_parameters 212 _refine_ls_number_restraints 88 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1629 _refine_ls_wR_factor_gt 0.1475 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.004 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 0.43256(6) 0.15737(6) 0.54110(6) 0.04179(18) Uani 1 1 d . . . O1 O 0.38166(5) 0.18462(5) 0.45313(5) 0.05268(17) Uani 1 1 d . . . C6 C 0.41587(6) 0.05961(6) 0.58383(7) 0.04222(18) Uani 1 1 d . C . C2 C 0.50205(6) 0.22824(6) 0.58360(6) 0.04232(19) Uani 1 1 d . C . C3 C 0.55632(7) 0.19785(7) 0.66862(7) 0.0494(2) Uani 1 1 d D . . H3 H 0.6045 0.2437 0.6962 0.059 Uiso 1 1 calc R A 1 C5 C 0.47233(7) 0.03325(7) 0.66920(7) 0.0488(2) Uani 1 1 d D . . H5 H 0.4632 -0.0325 0.6970 0.059 Uiso 1 1 calc R B 1 C8 C 0.51685(6) 0.33700(6) 0.54070(7) 0.0462(2) Uani 1 1 d . . . H8A H 0.5085 0.3343 0.4682 0.055 Uiso 1 1 calc R C . H8B H 0.5872 0.3601 0.5548 0.055 Uiso 1 1 calc R . . C4A C 0.54203(11) 0.10147(11) 0.71479(11) 0.0515(2) Uani 0.6846(15) 1 d PD C 1 C7A C 0.60950(13) 0.07412(12) 0.80680(12) 0.0719(3) Uani 0.6846(15) 1 d PD C 1 C10A C 0.5929(2) 0.15445(18) 0.89065(14) 0.1026(8) Uani 0.6846(15) 1 d PD C 1 H10A H 0.5209 0.1552 0.9098 0.154 Uiso 0.6846(15) 1 calc PR C 1 H10B H 0.6127 0.2221 0.8668 0.154 Uiso 0.6846(15) 1 calc PR C 1 H10C H 0.6348 0.1363 0.9479 0.154 Uiso 0.6846(15) 1 calc PR C 1 C11A C 0.72440(13) 0.0719(2) 0.77485(19) 0.1049(7) Uani 0.6846(15) 1 d PD C 1 H11A H 0.7442 0.1391 0.7499 0.157 Uiso 0.6846(15) 1 calc PR C 1 H11B H 0.7339 0.0209 0.7229 0.157 Uiso 0.6846(15) 1 calc PR C 1 H11C H 0.7669 0.0543 0.8318 0.157 Uiso 0.6846(15) 1 calc PR C 1 C9A C 0.5799(2) -0.03395(16) 0.8477(2) 0.1372(9) Uani 0.6846(15) 1 d PD C 1 H9B H 0.6223 -0.0499 0.9052 0.206 Uiso 0.6846(15) 1 calc PR C 1 H9A H 0.5911 -0.0853 0.7964 0.206 Uiso 0.6846(15) 1 calc PR C 1 H9C H 0.5080 -0.0341 0.8670 0.206 Uiso 0.6846(15) 1 calc PR C 1 C4B C 0.5485(2) 0.0979(2) 0.7095(2) 0.0515(2) Uani 0.3154(15) 1 d PD C 2 C7B C 0.6087(2) 0.0557(2) 0.8012(2) 0.0719(3) Uani 0.3154(15) 1 d PD C 2 C10B C 0.6782(4) 0.1426(3) 0.8435(4) 0.147(2) Uani 0.3154(15) 1 d PD C 2 H10D H 0.7348 0.1553 0.7980 0.221 Uiso 0.3154(15) 1 calc PR C 2 H10E H 0.7053 0.1217 0.9078 0.221 Uiso 0.3154(15) 1 calc PR C 2 H10F H 0.6380 0.2050 0.8513 0.221 Uiso 0.3154(15) 1 calc PR C 2 C11B C 0.6776(3) -0.0361(3) 0.7686(3) 0.1074(17) Uani 0.3154(15) 1 d PD C 2 H11D H 0.6344 -0.0922 0.7455 0.161 Uiso 0.3154(15) 1 calc PR C 2 H11E H 0.7185 -0.0591 0.8247 0.161 Uiso 0.3154(15) 1 calc PR C 2 H11F H 0.7228 -0.0143 0.7151 0.161 Uiso 0.3154(15) 1 calc PR C 2 C9B C 0.5318(3) 0.0181(4) 0.8819(3) 0.1135(19) Uani 0.3154(15) 1 d PD C 2 H9D H 0.4892 0.0753 0.9034 0.170 Uiso 0.3154(15) 1 calc PR C 2 H9E H 0.5696 -0.0089 0.9384 0.170 Uiso 0.3154(15) 1 calc PR C 2 H9F H 0.4884 -0.0356 0.8543 0.170 Uiso 0.3154(15) 1 calc PR C 2 F20 F 0.44532(18) 0.30523(8) 0.9201(2) 0.285(4) Uani 0.17 1 d PDU C -3 C21 C 0.34778(17) 0.27880(11) 0.8999(2) 0.079(2) Uani 0.1711(4) 1 d PGDU C -3 C22 C 0.2734(2) 0.2801(2) 0.9758(2) 0.0672(19) Uani 0.1711(4) 1 d PGDU C -3 H22 H 0.2920 0.2995 1.0408 0.081 Uiso 0.1711(4) 1 calc PR C -3 C23 C 0.17124(19) 0.2524(3) 0.9546(3) 0.095(2) Uani 0.1711(4) 1 d PGDU C -3 H23 H 0.1215 0.2533 1.0054 0.114 Uiso 0.1711(4) 1 calc PR C -3 C24 C 0.14345(19) 0.2234(3) 0.8575(3) 0.085(2) Uani 0.1711(4) 1 d PGDU C -3 H24 H 0.0751 0.2048 0.8433 0.102 Uiso 0.1711(4) 1 calc PR C -3 C25 C 0.2178(2) 0.2221(3) 0.7815(3) 0.0522(17) Uani 0.1711(4) 1 d PGDU C -3 H25 H 0.1992 0.2026 0.7165 0.063 Uiso 0.1711(4) 1 calc PR C -3 C26 C 0.3200(2) 0.2498(3) 0.8027(2) 0.100(3) Uani 0.1711(4) 1 d PGDU C -3 H26 H 0.3697 0.2489 0.7519 0.120 Uiso 0.1711(4) 1 calc PR C -3 F30 F 0.2365(3) 0.25319(7) 1.0848(2) 0.285(4) Uani 0.08 1 d PDU C -4 C31 C 0.2415(4) 0.24952(11) 0.9850(2) 0.0672(19) Uani 0.0789(4) 1 d PGD C -4 C32 C 0.1507(6) 0.2531(7) 0.9283(4) 0.095(2) Uani 0.0789(4) 1 d PGD C -4 H32 H 0.0865 0.2581 0.9602 0.114 Uiso 0.0789(4) 1 calc PR C -4 C33 C 0.1559(9) 0.2493(7) 0.8238(4) 0.085(2) Uani 0.0789(4) 1 d PGD C -4 H33 H 0.0952 0.2517 0.7858 0.102 Uiso 0.0789(4) 1 calc PR C -4 C34 C 0.2519(11) 0.2418(3) 0.7761(2) 0.0522(17) Uani 0.0789(4) 1 d PGD C -4 H34 H 0.2554 0.2393 0.7062 0.063 Uiso 0.0789(4) 1 calc PR C -4 C35 C 0.3426(9) 0.2382(8) 0.8329(4) 0.100(3) Uani 0.0789(4) 1 d PGD C -4 H35 H 0.4068 0.2333 0.8010 0.120 Uiso 0.0789(4) 1 calc PR C -4 C36 C 0.3374(5) 0.2421(8) 0.9374(4) 0.079(2) Uani 0.0789(4) 1 d PGD C -4 H36 H 0.3981 0.2397 0.9753 0.095 Uiso 0.0789(4) 1 calc PR C -4 H01A H 0.3223 0.1538 0.4494 0.100 Uiso 0.60 1 d P . . H01B H 0.3618 0.2551 0.4507 0.100 Uiso 0.40 1 d P . . 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 0.0375(3) 0.0413(4) 0.0465(4) -0.0038(3) 0.0067(3) 0.0036(3) O1 0.0547(3) 0.0524(3) 0.0509(3) 0.0005(3) -0.0005(3) 0.0001(3) C6 0.0364(3) 0.0373(3) 0.0530(4) -0.0061(3) 0.0061(3) 0.0014(3) C2 0.0356(3) 0.0381(3) 0.0533(4) -0.0015(3) 0.0089(3) 0.0010(3) C3 0.0439(4) 0.0441(4) 0.0603(5) -0.0018(4) -0.0023(4) -0.0052(3) C5 0.0454(4) 0.0408(4) 0.0602(5) 0.0035(4) 0.0013(4) -0.0021(3) C8 0.0370(3) 0.0416(4) 0.0601(5) 0.0029(3) 0.0094(3) -0.0017(3) C4A 0.0494(4) 0.0476(4) 0.0575(5) 0.0029(4) -0.0041(4) -0.0026(4) C7A 0.0808(7) 0.0592(7) 0.0758(7) 0.0123(5) -0.0282(6) -0.0129(6) C10A 0.1268(17) 0.1141(16) 0.0670(11) 0.0028(11) -0.0267(11) -0.0170(14) C11A 0.0783(11) 0.1087(16) 0.1278(16) -0.0053(13) -0.0502(11) 0.0188(11) C9A 0.175(2) 0.0902(13) 0.1466(17) 0.0594(12) -0.0956(15) -0.0439(14) C4B 0.0494(4) 0.0476(4) 0.0575(5) 0.0029(4) -0.0041(4) -0.0026(4) C7B 0.0808(7) 0.0592(7) 0.0758(7) 0.0123(5) -0.0282(6) -0.0129(6) C10B 0.190(5) 0.141(4) 0.111(3) 0.052(3) -0.096(3) -0.074(4) C11B 0.096(3) 0.140(4) 0.086(3) 0.022(3) -0.024(2) 0.043(3) C9B 0.110(4) 0.162(5) 0.069(2) 0.052(3) -0.002(2) 0.006(4) F20 0.118(5) 0.381(11) 0.356(9) -0.218(9) -0.074(6) -0.010(7) C21 0.081(4) 0.119(5) 0.039(3) -0.011(3) -0.011(3) -0.010(4) C22 0.079(4) 0.061(5) 0.0610(17) -0.003(3) -0.003(5) 0.000(3) C23 0.069(4) 0.165(6) 0.052(4) -0.010(5) -0.013(3) 0.027(5) C24 0.068(3) 0.143(6) 0.045(4) -0.003(4) 0.017(3) -0.021(4) C25 0.058(4) 0.033(3) 0.0660(18) -0.0090(19) 0.007(3) -0.0199(16) C26 0.027(3) 0.203(7) 0.070(4) -0.036(6) -0.019(3) 0.023(4) F30 0.118(5) 0.381(11) 0.356(9) -0.218(9) -0.074(6) -0.010(7) C31 0.079(4) 0.061(5) 0.0610(17) -0.003(3) -0.003(5) 0.000(3) C32 0.069(4) 0.165(6) 0.052(4) -0.010(5) -0.013(3) 0.027(5) C33 0.068(3) 0.143(6) 0.045(4) -0.003(4) 0.017(3) -0.021(4) C34 0.058(4) 0.033(3) 0.0660(18) -0.0090(19) 0.007(3) -0.0199(16) C35 0.027(3) 0.203(7) 0.070(4) -0.036(6) -0.019(3) 0.023(4) C36 0.081(4) 0.119(5) 0.039(3) -0.011(3) -0.011(3) -0.010(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.3845(10) . ? C1 C2 1.3954(11) . ? C1 C6 1.3958(11) . ? C6 C5 1.3885(13) . ? C6 C8 1.5242(11) 4 ? C2 C3 1.3838(13) . ? C2 C8 1.5221(11) . ? C3 C4A 1.3949(17) . ? C3 C4B 1.399(3) . ? C5 C4B 1.392(3) . ? C5 C4A 1.3926(17) . ? C8 C6 1.5242(11) 3 ? C4A C7A 1.539(2) . ? C7A C10A 1.534(2) . ? C7A C11A 1.537(2) . ? C7A C9A 1.540(2) . ? C4B C7B 1.541(3) . ? C7B C9B 1.537(4) . ? C7B C10B 1.537(4) . ? C7B C11B 1.539(4) . ? F20 C21 1.327(3) . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? F30 C31 1.327(3) . ? C31 C32 1.3900 . ? C31 C36 1.3900 . ? C32 C33 1.3900 . ? C33 C34 1.3900 . ? C34 C35 1.3900 . ? C35 C36 1.3900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 118.61(7) . . ? O1 C1 C6 119.90(7) . . ? C2 C1 C6 121.47(8) . . ? C5 C6 C1 118.13(7) . . ? C5 C6 C8 119.83(7) . 4 ? C1 C6 C8 122.03(8) . 4 ? C3 C2 C1 117.95(7) . . ? C3 C2 C8 120.12(7) . . ? C1 C2 C8 121.91(8) . . ? C2 C3 C4A 122.90(9) . . ? C2 C3 C4B 122.70(14) . . ? C4A C3 C4B 4.84(17) . . ? C6 C5 C4B 122.45(13) . . ? C6 C5 C4A 122.54(9) . . ? C4B C5 C4A 4.86(17) . . ? C2 C8 C6 112.95(7) . 3 ? C5 C4A C3 116.95(11) . . ? C5 C4A C7A 124.33(12) . . ? C3 C4A C7A 118.54(12) . . ? C10A C7A C11A 110.27(17) . . ? C10A C7A C4A 110.15(14) . . ? C11A C7A C4A 109.07(14) . . ? C10A C7A C9A 108.49(17) . . ? C11A C7A C9A 108.53(18) . . ? C4A C7A C9A 110.32(15) . . ? C5 C4B C3 116.7(2) . . ? C5 C4B C7B 116.6(2) . . ? C3 C4B C7B 126.5(2) . . ? C9B C7B C10B 110.3(3) . . ? C9B C7B C11B 109.0(3) . . ? C10B C7B C11B 109.0(3) . . ? C9B C7B C4B 109.8(3) . . ? C10B C7B C4B 109.0(3) . . ? C11B C7B C4B 109.7(3) . . ? F20 C21 C22 120.04(16) . . ? F20 C21 C26 119.96(16) . . ? C22 C21 C26 120.0 . . ? C21 C22 C23 120.0 . . ? C24 C23 C22 120.0 . . ? C23 C24 C25 120.0 . . ? C24 C25 C26 120.0 . . ? C25 C26 C21 120.0 . . ? F30 C31 C32 120.0(2) . . ? F30 C31 C36 120.0(2) . . ? C32 C31 C36 120.0 . . ? C33 C32 C31 120.0 . . ? C32 C33 C34 120.0 . . ? C35 C34 C33 120.0 . . ? C34 C35 C36 120.0 . . ? C35 C36 C31 120.0 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.70 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.367 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.032 #===END data_CRYSTALS_cif _database_code_depnum_ccdc_archive 'CCDC 237581' _audit_creation_date 03-07-11 _audit_creation_method CRYSTALS_ver_12-03-99 _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms placed geometrically after each cycle ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment mixed #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2001) ; _computing_publication_material ; CRYSTALS (Watkin et al 2001) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 17.910(2) _cell_angle_alpha 90 _cell_length_b 13.4672(17) _cell_angle_beta 90.171(2) _cell_length_c 17.840(2) _cell_angle_gamma 90 _cell_volume 4302.9(9) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 2/c 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y,-z+1/2 x,-y,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'F ' 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 4 _chemical_formula_sum ' C50 H59 F3 O4 ' _chemical_formula_moiety ' C50 H59 F3 O4 ' _chemical_compound_source ; ? ; _chemical_formula_weight 781.01 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 293 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' white ' _exptl_crystal_size_min 0.00 _exptl_crystal_size_mid 0.00 _exptl_crystal_size_max 0.00 _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1672.000 _exptl_absorpt_coefficient_mu 0.083 # Sheldrick geometric definitions 1.00 1.00 _diffrn_measurement_device_type ; Unknown ; _diffrn_radiation_monochromator graphite _computing_data_collection ; DATA COLLECTION ; _computing_data_reduction ; USER DEFINED 5 ; _computing_cell_refinement ; USER DEFINED 6 ; _computing_structure_solution ; SHELXS 86 (Sheldrick, 1986) ; _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 1.00 _exptl_absorpt_correction_T_max 1.00 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 293 _diffrn_reflns_number 54364 _reflns_number_total 12159 _diffrn_reflns_av_R_equivalents 0.05 # Number of reflections with Friedels Law is 12159 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 12289 _diffrn_reflns_theta_min 1.512 _diffrn_reflns_theta_max 29.769 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 29.173 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -24 _reflns_limit_h_max 24 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _refine_diff_density_min -0.43 _refine_diff_density_max 0.41 _refine_ls_number_reflns 12122 _refine_ls_number_restraints 8 _refine_ls_number_parameters 523 #_refine_ls_R_factor_ref 0.1018 _refine_ls_wR_factor_ref 0.1507 _refine_ls_goodness_of_fit_ref 0.7635 #_reflns_number_all 12122 _refine_ls_R_factor_all 0.1018 _refine_ls_wR_factor_all 0.1507 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.00u(I) _reflns_number_gt 6087 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_gt 0.1376 _refine_ls_shift/su_max 0.000288 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; p=P(6)*max(Fo^2,0) + (1-P(6))Fc^2 Method = SHELXL 97 (Sheldrick, 1997) W = 1. / [Sigma^2(F*)+(P(1)p)^2+P(2)p+P(4)+P(5)Sin(theta) ] P(i) are: 0.859E-01 0.00 0.00 0.00 0.00 0.333 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined data collection reference Spare 5 Spare 6 Sheldrick, G.M. (1986). SHELXS86. Program for the solution of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Sheldrick, G.M. (1997). SHELXL-97. Program for the refinement of crystal structures. Univ. of Gottingen, Federal Republic of Germany. Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper R.I. (2001) CRYSTALS Issue 11. Chemical Crystallography Laboratory, OXFORD, UK. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_refinement_flags _atom_site_attached_hydrogens O1 O 0.1013 0.5350 0.2827 0.0288 1.0000 Uani . . O2 O 0.0311 0.5309 0.1520 0.0278 1.0000 Uani . . O3 O 0.4660 0.4419 0.3523 0.0305 1.0000 Uani . . O4 O 0.4017 0.4464 0.2162 0.0300 1.0000 Uani . . C1 C 0.1390 0.4466 0.2930 0.0222 1.0000 Uani . . C2 C 0.1384 0.4025 0.3640 0.0230 1.0000 Uani . . C3 C 0.1779 0.3157 0.3736 0.0254 1.0000 Uani . . H203 H 0.1769 0.2844 0.4213 0.0500 1.0000 Uiso . . C4 C 0.2186 0.2706 0.3164 0.0246 1.0000 Uani . . C5 C 0.2169 0.3177 0.2469 0.0249 1.0000 Uani . . H5 H 0.2439 0.2883 0.2068 0.0500 1.0000 Uiso . . C6 C 0.1783 0.4038 0.2335 0.0220 1.0000 Uani . . C7 C 0.2633 0.1762 0.3325 0.0336 1.0000 Uani . . C8 C 0.0937 0.4470 0.4287 0.0266 1.0000 Uani . . H801 H 0.1200 0.4328 0.4764 0.0500 1.0000 Uiso . . H802 H 0.0918 0.5200 0.4230 0.0500 1.0000 Uiso . . C9 C 0.3010 0.1347 0.2614 0.0511 1.0000 Uani . . H901 H 0.2627 0.1199 0.2236 0.0500 1.0000 Uiso . . H902 H 0.3290 0.0746 0.2730 0.0500 1.0000 Uiso . . H903 H 0.3360 0.1852 0.2410 0.0500 1.0000 Uiso . . C10 C 0.2121 0.0957 0.3639 0.0465 1.0000 Uani . . H101 H 0.1728 0.0812 0.3271 0.0500 1.0000 Uiso . . H102 H 0.1896 0.1169 0.4102 0.0500 1.0000 Uiso . . H103 H 0.2416 0.0342 0.3728 0.0500 1.0000 Uiso . . C11 C 0.3249 0.1994 0.3897 0.0463 1.0000 Uani . . H111 H 0.3539 0.1392 0.4001 0.0500 1.0000 Uiso . . H112 H 0.3018 0.2234 0.4360 0.0500 1.0000 Uiso . . H113 H 0.3576 0.2508 0.3692 0.0500 1.0000 Uiso . . C21 C 0.0437 0.4484 0.1079 0.0232 1.0000 Uani . . C22 C 0.1149 0.4089 0.1054 0.0223 1.0000 Uani . . C23 C 0.1285 0.3293 0.0574 0.0248 1.0000 Uani . . H23 H 0.1775 0.3024 0.0550 0.0500 1.0000 Uiso . . C24 C 0.0731 0.2868 0.0132 0.0250 1.0000 Uani . . C25 C 0.0008 0.3272 0.0195 0.0267 1.0000 Uani . . H25 H -0.0385 0.2993 -0.0094 0.0500 1.0000 Uiso . . C26 C -0.0151 0.4068 0.0662 0.0237 1.0000 Uani . . C27 C 0.0874 0.2010 -0.0407 0.0312 1.0000 Uani . . C28 C 0.1775 0.4494 0.1548 0.0235 1.0000 Uani . . H281 H 0.1711 0.5221 0.1593 0.0500 1.0000 Uiso . . H282 H 0.2253 0.4372 0.1301 0.0500 1.0000 Uiso . . C29 C 0.0765 0.2388 -0.1219 0.0450 1.0000 Uani . . H291 H 0.0260 0.2656 -0.1277 0.0500 1.0000 Uiso . . H292 H 0.0836 0.1841 -0.1577 0.0500 1.0000 Uiso . . H293 H 0.1130 0.2913 -0.1326 0.0500 1.0000 Uiso . . C30 C 0.0310 0.1181 -0.0278 0.0497 1.0000 Uani . . H301 H -0.0199 0.1441 -0.0327 0.0500 1.0000 Uiso . . H302 H 0.0385 0.0906 0.0219 0.0500 1.0000 Uiso . . H303 H 0.0393 0.0653 -0.0658 0.0500 1.0000 Uiso . . C31 C 0.1639 0.1598 -0.0332 0.0601 1.0000 Uani . . H311 H 0.1999 0.2134 -0.0415 0.0500 1.0000 Uiso . . H312 H 0.1725 0.1083 -0.0715 0.0500 1.0000 Uiso . . H313 H 0.1717 0.1334 0.0162 0.0500 1.0000 Uiso . . C41 C 0.4564 0.5317 0.3889 0.0232 1.0000 Uani . . C42 C 0.5149 0.5761 0.4271 0.0228 1.0000 Uani . . C43 C 0.5017 0.6664 0.4633 0.0264 1.0000 Uani . . H43 H 0.5415 0.6969 0.4901 0.0500 1.0000 Uiso . . C44 C 0.4325 0.7125 0.4620 0.0286 1.0000 Uani . . C45 C 0.3754 0.6638 0.4231 0.0269 1.0000 Uani . . H45 H 0.3272 0.6933 0.4225 0.0500 1.0000 Uiso . . C46 C 0.3853 0.5752 0.3868 0.0230 1.0000 Uani . . C47 C 0.4171 0.8107 0.5026 0.0366 1.0000 Uani . . C48 C 0.5931 0.5322 0.4293 0.0247 1.0000 Uani . . H481 H 0.5894 0.4591 0.4248 0.0500 1.0000 Uiso . . H482 H 0.6163 0.5475 0.4788 0.0500 1.0000 Uiso . . C49 C 0.3836 0.8857 0.4468 0.0479 1.0000 Uani . . H491 H 0.3379 0.8575 0.4251 0.0500 1.0000 Uiso . . H492 H 0.4185 0.9005 0.4060 0.0500 1.0000 Uiso . . H493 H 0.3707 0.9481 0.4726 0.0500 1.0000 Uiso . . C50 C 0.3611 0.7922 0.5661 0.0488 1.0000 Uani . . H501 H 0.3156 0.7628 0.5451 0.0500 1.0000 Uiso . . H502 H 0.3484 0.8552 0.5902 0.0500 1.0000 Uiso . . H503 H 0.3826 0.7466 0.6025 0.0500 1.0000 Uiso . . C51 C 0.4872 0.8567 0.5349 0.0538 1.0000 Uani . . H511 H 0.4746 0.9195 0.5595 0.0500 1.0000 Uiso . . H512 H 0.5231 0.8688 0.4947 0.0500 1.0000 Uiso . . H513 H 0.5086 0.8108 0.5715 0.0500 1.0000 Uiso . . C61 C 0.3591 0.5303 0.2042 0.0232 1.0000 Uani . . C62 C 0.3169 0.5707 0.2630 0.0233 1.0000 Uani . . C63 C 0.2736 0.6528 0.2480 0.0233 1.0000 Uani . . H63 H 0.2446 0.6804 0.2873 0.0500 1.0000 Uiso . . C64 C 0.2699 0.6980 0.1772 0.0246 1.0000 Uani . . C65 C 0.3126 0.6547 0.1210 0.0233 1.0000 Uani . . H65 H 0.3110 0.6830 0.0723 0.0500 1.0000 Uiso . . C66 C 0.3577 0.5725 0.1328 0.0226 1.0000 Uani . . C67 C 0.2196 0.7879 0.1649 0.0289 1.0000 Uani . . C68 C 0.3220 0.5292 0.3422 0.0251 1.0000 Uani . . H681 H 0.2743 0.5406 0.3689 0.0500 1.0000 Uiso . . H681' H 0.3309 0.4567 0.3396 0.0500 1.0000 Uiso . . C69 C 0.2322 0.8371 0.0890 0.0486 1.0000 Uani . . H691 H 0.1990 0.8945 0.0840 0.0500 1.0000 Uiso . . H692 H 0.2221 0.7892 0.0486 0.0500 1.0000 Uiso . . H693 H 0.2849 0.8589 0.0849 0.0500 1.0000 Uiso . . C70 C 0.2339 0.8656 0.2258 0.0396 1.0000 Uani . . H701 H 0.2264 0.8353 0.2752 0.0500 1.0000 Uiso . . H702 H 0.1990 0.9213 0.2196 0.0500 1.0000 Uiso . . H703 H 0.2853 0.8909 0.2226 0.0500 1.0000 Uiso . . C71 C 0.1375 0.7549 0.1691 0.0396 1.0000 Uani . . H711 H 0.1288 0.7226 0.2175 0.0500 1.0000 Uiso . . H712 H 0.1268 0.7068 0.1290 0.0500 1.0000 Uiso . . H713 H 0.1047 0.8117 0.1648 0.0500 1.0000 Uiso . . C81 C 0.0000 0.2214 0.2500 0.0311 1.0000 Uani . . C82 C 0.0458 0.1731 0.2007 0.0385 1.0000 Uani . . H82 H 0.0779 0.2083 0.1677 0.0500 1.0000 Uiso . . C83 C 0.0441 0.0728 0.2021 0.0457 1.0000 Uani . . C84 C 0.0000 0.0174 0.2500 0.0472 1.0000 Uani . . H84 H 0.0000 -0.0532 0.2500 0.0500 1.0000 Uiso . . F81 F 0.0000 0.3211 0.2500 0.0441 1.0000 Uani . . F82 F 0.0893 0.0216 0.1547 0.0754 1.0000 Uani . . F91 F 0.5000 0.6681 0.2500 0.0470 1.0000 Uani . . F92 F 0.4080 0.9671 0.1564 0.0712 1.0000 Uani . . C91 C 0.5000 0.7678 0.2500 0.0335 1.0000 Uani . . C92 C 0.4524 0.8163 0.2018 0.0367 1.0000 Uani . . H92 H 0.4203 0.7806 0.1690 0.0500 1.0000 Uiso . . C93 C 0.4544 0.9167 0.2037 0.0460 1.0000 Uani . . C94 C 0.5000 0.9709 0.2500 0.0459 1.0000 Uani . . H94 H 0.5000 1.0414 0.2500 0.0500 1.0000 Uiso . . H203' H 0.5108 0.4218 0.3600 0.0734 1.0000 Uiso . . H204 H 0.4278 0.4471 0.2649 0.0289 1.0000 Uiso . . H202 H -0.0106 0.5749 0.1381 0.0702 1.0000 Uiso . . H201 H 0.0676 0.5456 0.2389 0.0423 1.0000 Uiso . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0312 0.0307 0.0245 0.0002 -0.0019 0.0011 O2 0.0321 0.0252 0.0260 -0.0017 0.0006 0.0028 O3 0.0304 0.0291 0.0319 0.0010 0.0003 0.0008 O4 0.0304 0.0311 0.0286 -0.0003 -0.0014 0.0029 C1 0.0226 0.0236 0.0204 -0.0017 -0.0029 -0.0046 C2 0.0199 0.0303 0.0187 -0.0024 0.0001 -0.0079 C3 0.0248 0.0322 0.0192 0.0026 -0.0014 -0.0022 C4 0.0235 0.0290 0.0214 -0.0019 0.0002 -0.0011 C5 0.0215 0.0323 0.0208 -0.0021 0.0008 -0.0047 C6 0.0204 0.0279 0.0176 -0.0010 0.0020 -0.0076 C7 0.0387 0.0358 0.0264 0.0037 0.0024 0.0077 C8 0.0274 0.0347 0.0178 -0.0012 -0.0010 -0.0004 C9 0.0670 0.0456 0.0408 0.0029 0.0140 0.0223 C10 0.0579 0.0365 0.0452 0.0067 0.0064 -0.0005 C11 0.0380 0.0562 0.0447 0.0061 -0.0079 0.0095 C21 0.0278 0.0255 0.0164 0.0026 0.0030 -0.0017 C22 0.0238 0.0266 0.0165 0.0035 -0.0007 -0.0064 C23 0.0245 0.0297 0.0203 0.0013 0.0039 -0.0008 C24 0.0242 0.0309 0.0200 0.0023 0.0021 -0.0015 C25 0.0282 0.0344 0.0174 -0.0010 0.0014 -0.0052 C26 0.0235 0.0288 0.0189 0.0060 0.0023 -0.0015 C27 0.0289 0.0324 0.0323 -0.0043 0.0006 -0.0001 C28 0.0247 0.0299 0.0159 0.0006 0.0014 -0.0037 C29 0.0576 0.0474 0.0299 -0.0046 0.0070 -0.0017 C30 0.0631 0.0419 0.0441 -0.0079 0.0055 -0.0103 C31 0.0486 0.0587 0.0729 -0.0305 -0.0101 0.0134 C41 0.0262 0.0248 0.0187 0.0051 0.0016 -0.0022 C42 0.0271 0.0275 0.0138 0.0051 0.0028 0.0004 C43 0.0240 0.0335 0.0216 0.0022 0.0001 -0.0021 C44 0.0288 0.0323 0.0247 0.0008 0.0044 0.0013 C45 0.0222 0.0362 0.0223 0.0056 -0.0009 0.0014 C46 0.0244 0.0301 0.0144 0.0041 0.0015 -0.0038 C47 0.0254 0.0399 0.0444 -0.0115 0.0049 -0.0008 C48 0.0255 0.0321 0.0165 0.0063 0.0007 0.0022 C49 0.0431 0.0414 0.0593 -0.0042 0.0062 0.0014 C50 0.0475 0.0625 0.0365 -0.0129 0.0090 0.0100 C51 0.0361 0.0565 0.0687 -0.0286 -0.0052 0.0005 C61 0.0236 0.0236 0.0223 -0.0019 -0.0022 -0.0033 C62 0.0225 0.0309 0.0165 -0.0009 0.0018 -0.0068 C63 0.0210 0.0328 0.0161 -0.0039 0.0018 -0.0042 C64 0.0228 0.0265 0.0246 -0.0025 0.0006 -0.0027 C65 0.0247 0.0267 0.0186 -0.0013 0.0011 -0.0061 C66 0.0222 0.0278 0.0177 -0.0059 -0.0013 -0.0082 C67 0.0304 0.0326 0.0237 -0.0009 0.0010 0.0009 C68 0.0222 0.0324 0.0206 0.0036 0.0018 -0.0033 C69 0.0605 0.0501 0.0352 0.0099 0.0102 0.0198 C70 0.0421 0.0322 0.0446 -0.0059 -0.0002 0.0029 C71 0.0352 0.0386 0.0450 -0.0005 -0.0045 0.0076 C81 0.0354 0.0324 0.0255 0.0000 -0.0064 0.0000 C82 0.0355 0.0489 0.0311 0.0061 0.0025 0.0051 C83 0.0527 0.0500 0.0345 -0.0075 -0.0059 0.0137 C84 0.0676 0.0311 0.0429 0.0000 -0.0182 0.0000 F81 0.0525 0.0359 0.0439 0.0000 0.0007 0.0000 F82 0.0882 0.0760 0.0619 -0.0188 0.0074 0.0393 F91 0.0537 0.0370 0.0504 0.0000 0.0009 0.0000 F92 0.0580 0.0762 0.0794 0.0373 -0.0045 0.0101 C91 0.0422 0.0339 0.0244 0.0000 0.0122 0.0000 C92 0.0324 0.0470 0.0308 0.0033 0.0001 -0.0045 C93 0.0351 0.0581 0.0447 0.0188 0.0077 0.0055 C94 0.0513 0.0320 0.0545 0.0000 0.0158 0.0000 _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . H201 . 0.995 no O1 . C1 . 1.38092(14) yes O2 . H202 . 0.986 no O2 . C21 . 1.37999(13) yes O3 . H203 . 0.857 no O3 . C41 . 1.38495(14) yes O4 . H204 . 0.985 no O4 . C61 . 1.38013(13) yes C1 . C6 . 1.39925(11) yes C1 . C2 . 1.39864(14) yes C2 . C8 . 1.52887(12) yes C2 . C3 . 1.37774(13) yes C3 . C4 . 1.39383(11) yes C3 . H203 . 0.950 no C4 . C7 . 1.52938(14) yes C4 . C5 . 1.39325(14) yes C5 . C6 . 1.37059(13) yes C5 . H5 . 0.950 no C6 . C28 . 1.53291(16) yes C7 . C11 . 1.53381(13) yes C7 . C10 . 1.52740(12) yes C7 . C9 . 1.54421(14) yes C8 . H802 . 0.988 no C8 . H801 . 0.990 no C8 . C26 3_555 1.51195(16) yes C9 . H903 . 0.994 no C9 . H902 . 0.973 no C9 . H901 . 0.980 no C10 . H103 . 0.995 no C10 . H102 . 0.965 no C10 . H101 . 0.980 no C11 . H113 . 0.978 no C11 . H112 . 0.979 no C11 . H111 . 0.980 no C21 . C26 . 1.40450(11) yes C21 . C22 . 1.38306(15) yes C22 . C28 . 1.52375(12) yes C22 . C23 . 1.39348(12) yes C23 . C24 . 1.38863(11) yes C23 . H23 . 0.950 no C24 . C27 . 1.52676(13) yes C24 . C25 . 1.40917(15) yes C25 . C26 . 1.38682(12) yes C25 . H25 . 0.950 no C27 . C31 . 1.48312(16) yes C27 . C30 . 1.52296(13) yes C27 . C29 . 1.54716(17) yes C28 . H282 . 0.978 no C28 . H281 . 0.990 no C29 . H293 . 0.982 no C29 . H292 . 0.983 no C29 . H291 . 0.980 no C30 . H303 . 0.994 no C30 . H302 . 0.969 no C30 . H301 . 0.980 no C31 . H313 . 0.961 no C31 . H312 . 0.985 no C31 . H311 . 0.980 no C41 . C46 . 1.40234(15) yes C41 . C42 . 1.38372(11) yes C42 . C48 . 1.51993(16) yes C42 . C43 . 1.39778(14) yes C43 . C44 . 1.38610(14) yes C43 . H43 . 0.950 no C44 . C47 . 1.53302(15) yes C44 . C45 . 1.39750(11) yes C45 . C46 . 1.36994(14) yes C45 . H45 . 0.950 no C46 . C68 . 1.51651(12) yes C47 . C51 . 1.51134(14) yes C47 . C50 . 1.53487(13) yes C47 . C49 . 1.54039(12) yes C48 . H482 . 0.996 no C48 . H481 . 0.990 no C48 . C66 3_655 1.51834(12) yes C49 . H493 . 0.985 no C49 . H492 . 0.982 no C49 . H491 . 0.980 no C50 . H503 . 0.973 no C50 . H502 . 0.979 no C50 . H501 . 0.980 no C51 . H513 . 0.976 no C51 . H512 . 0.980 no C51 . H511 . 0.980 no C61 . C66 . 1.39517(15) yes C61 . C62 . 1.40421(11) yes C62 . C68 . 1.52189(16) yes C62 . C63 . 1.37660(12) yes C63 . C64 . 1.40198(14) yes C63 . H63 . 0.950 no C64 . C67 . 1.52453(14) yes C64 . C65 . 1.39083(11) yes C65 . C66 . 1.38608(13) yes C65 . H65 . 0.950 no C67 . C71 . 1.53917(17) yes C67 . C70 . 1.53008(13) yes C67 . C69 . 1.52575(15) yes C68 . H681 . 0.991 no C68 . H681 . 0.990 no C69 . H693 . 0.991 no C69 . H692 . 0.983 no C69 . H691 . 0.980 no C70 . H703 . 0.983 no C70 . H702 . 0.983 no C70 . H701 . 0.980 no C71 . H713 . 0.967 no C71 . H712 . 0.983 no C71 . H711 . 0.980 no C81 . F81 . 1.34223(17) yes C81 . C82 . 1.3688(1) yes C81 . C82 3_555 1.3688(1) yes C82 . C83 . 1.35066(17) yes C82 . H82 . 0.950 no C83 . F82 . 1.3606(1) yes C83 . C84 . 1.3842(1) yes C84 . H84 . 0.950 no F91 . C91 . 1.34208(17) yes F92 . C93 . 1.3634(1) yes C91 . C92 . 1.3741(1) yes C91 . C92 3_655 1.3741(1) yes C92 . C93 . 1.35420(17) yes C92 . H92 . 0.950 no C93 . C94 . 1.3703(1) yes C94 . H94 . 0.950 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H201 . O1 . C1 . 121.568 no H202 . O2 . C21 . 117.705 no H203 . O3 . C41 . 108.557 no H204 . O4 . C61 . 112.883 no C6 . C1 . C2 . 121.154(8) yes C6 . C1 . O1 . 120.076(8) yes C2 . C1 . O1 . 118.756(7) yes C8 . C2 . C3 . 120.548(8) yes C8 . C2 . C1 . 121.556(8) yes C3 . C2 . C1 . 117.876(3) yes C4 . C3 . H203 . 118.320 no C4 . C3 . C2 . 123.207(8) yes H203 . C3 . C2 . 118.467 no C7 . C4 . C5 . 123.678(3) yes C7 . C4 . C3 . 119.969(3) yes C5 . C4 . C3 . 116.333(7) yes C6 . C5 . H5 . 118.575 no C6 . C5 . C4 . 123.340 yes H5 . C5 . C4 . 118.084 no C28 . C6 . C5 . 120.135(6) yes C28 . C6 . C1 . 121.770(6) yes C5 . C6 . C1 . 118.083(3) yes C11 . C7 . C10 . 109.392(8) yes C11 . C7 . C9 . 107.737(11) yes C10 . C7 . C9 . 107.970(9) yes C11 . C7 . C4 . 109.304(3) yes C10 . C7 . C4 . 110.16(1) yes C9 . C7 . C4 . 112.208(9) yes H802 . C8 . H801 . 107.266 no H802 . C8 . C26 3_555 109.315 no H801 . C8 . C26 3_555 108.596 no H802 . C8 . C2 . 109.282 no H801 . C8 . C2 . 108.979 no C26 3_555 C8 . C2 . 113.228(4) yes H903 . C9 . H902 . 108.863 no H903 . C9 . H901 . 109.153 no H902 . C9 . H901 . 109.575 no H903 . C9 . C7 . 109.293 no H902 . C9 . C7 . 110.653 no H901 . C9 . C7 . 109.281 no H103 . C10 . H102 . 109.466 no H103 . C10 . H101 . 108.726 no H102 . C10 . H101 . 109.327 no H103 . C10 . C7 . 109.314 no H102 . C10 . C7 . 110.940 no H101 . C10 . C7 . 109.032 no H113 . C11 . H112 . 109.721 no H113 . C11 . H111 . 109.797 no H112 . C11 . H111 . 109.779 no H113 . C11 . C7 . 109.000 no H112 . C11 . C7 . 108.864 no H111 . C11 . C7 . 109.661 no C26 . C21 . C22 . 121.272(8) yes C26 . C21 . O2 . 120.009(8) yes C22 . C21 . O2 . 118.717(6) yes C28 . C22 . C23 . 120.070(8) yes C28 . C22 . C21 . 121.314(8) yes C23 . C22 . C21 . 118.607(4) yes C24 . C23 . H23 . 118.419 no C24 . C23 . C22 . 122.672(8) yes H23 . C23 . C22 . 118.905 no C27 . C24 . C25 . 119.946(4) yes C27 . C24 . C23 . 123.274(4) yes C25 . C24 . C23 . 116.778(6) yes C26 . C25 . H25 . 118.590 no C26 . C25 . C24 . 122.468(3) yes H25 . C25 . C24 . 118.941 no C25 . C26 . C21 . 118.124(4) yes C25 . C26 . C8 3_555 120.410(4) yes C21 . C26 . C8 3_555 121.466(8) yes C31 . C27 . C30 . 108.968(5) yes C31 . C27 . C29 . 108.763(6) yes C30 . C27 . C29 . 107.516(6) yes C31 . C27 . C24 . 112.524(6) yes C30 . C27 . C24 . 110.273(8) yes C29 . C27 . C24 . 108.660(5) yes H282 . C28 . H281 . 107.717 no H282 . C28 . C22 . 108.863 no H281 . C28 . C22 . 108.443 no H282 . C28 . C6 . 109.835 no H281 . C28 . C6 . 108.791 no C22 . C28 . C6 . 113.046(9) yes H293 . C29 . H292 . 109.088 no H293 . C29 . H291 . 109.199 no H292 . C29 . H291 . 109.184 no H293 . C29 . C27 . 109.661 no H292 . C29 . C27 . 110.144 no H291 . C29 . C27 . 109.545 no H303 . C30 . H302 . 109.193 no H303 . C30 . H301 . 109.629 no H302 . C30 . H301 . 110.145 no H303 . C30 . C27 . 108.731 no H302 . C30 . C27 . 109.143 no H301 . C30 . C27 . 109.973 no H313 . C31 . H312 . 110.637 no H313 . C31 . H311 . 108.479 no H312 . C31 . H311 . 108.008 no H313 . C31 . C27 . 110.721 no H312 . C31 . C27 . 110.277 no H311 . C31 . C27 . 108.637 no C46 . C41 . C42 . 121.200(6) yes C46 . C41 . O3 . 117.799(7) yes C42 . C41 . O3 . 120.996(8) yes C48 . C42 . C43 . 118.925(6) yes C48 . C42 . C41 . 122.674(6) yes C43 . C42 . C41 . 118.379(3) yes C44 . C43 . H43 . 118.898 no C44 . C43 . C42 . 122.300(6) yes H43 . C43 . C42 . 118.800 no C47 . C44 . C45 . 120.469(3) yes C47 . C44 . C43 . 122.694(3) yes C45 . C44 . C43 . 116.814(9) yes C46 . C45 . H45 . 118.505 no C46 . C45 . C44 . 123.216(3) yes H45 . C45 . C44 . 118.273 no C68 . C46 . C45 . 120.393(8) yes C68 . C46 . C41 . 121.438(8) yes C45 . C46 . C41 . 118.085(3) yes C51 . C47 . C50 . 109.219(6) yes C51 . C47 . C49 . 107.457(6) yes C50 . C47 . C49 . 109.177(8) yes C51 . C47 . C44 . 112.54(1) yes C50 . C47 . C44 . 109.105 yes C49 . C47 . C44 . 109.28(1) yes H482 . C48 . H481 . 107.725 no H482 . C48 . C66 3_655 109.307 no H481 . C48 . C66 3_655 109.600 no H482 . C48 . C42 . 108.975 no H481 . C48 . C42 . 108.899 no C66 3_655 C48 . C42 . 112.227(9) yes H493 . C49 . H492 . 108.873 no H493 . C49 . H491 . 108.622 no H492 . C49 . H491 . 108.692 no H493 . C49 . C47 . 110.328 no H492 . C49 . C47 . 111.324 no H491 . C49 . C47 . 108.946 no H503 . C50 . H502 . 110.189 no H503 . C50 . H501 . 109.054 no H502 . C50 . H501 . 108.928 no H503 . C50 . C47 . 109.713 no H502 . C50 . C47 . 109.749 no H501 . C50 . C47 . 109.185 no H513 . C51 . H512 . 109.767 no H513 . C51 . H511 . 109.730 no H512 . C51 . H511 . 109.653 no H513 . C51 . C47 . 108.664 no H512 . C51 . C47 . 109.620 no H511 . C51 . C47 . 109.389 no C66 . C61 . C62 . 121.101(6) yes C66 . C61 . O4 . 118.855(6) yes C62 . C61 . O4 . 120.034(8) yes C68 . C62 . C63 . 120.555(6) yes C68 . C62 . C61 . 121.365(6) yes C63 . C62 . C61 . 117.990(4) yes C64 . C63 . H63 . 118.126 no C64 . C63 . C62 . 123.291(6) yes H63 . C63 . C62 . 118.583 no C67 . C64 . C65 . 123.692(3) yes C67 . C64 . C63 . 119.995(3) yes C65 . C64 . C63 . 116.295(8) yes C66 . C65 . H65 . 118.432 no C66 . C65 . C64 . 123.122(3) yes H65 . C65 . C64 . 118.445 no C65 . C66 . C61 . 118.189(4) yes C65 . C66 . C48 3_655 120.938(4) yes C61 . C66 . C48 3_655 120.820(6) yes C71 . C67 . C70 . 108.738(6) yes C71 . C67 . C69 . 108.188(6) yes C70 . C67 . C69 . 107.968(11) yes C71 . C67 . C64 . 109.184(4) yes C70 . C67 . C64 . 110.078(8) yes C69 . C67 . C64 . 112.596(7) yes H681 . C68 . H681 . 108.431 no H681 . C68 . C46 . 107.836 no H681 . C68 . C46 . 109.223 no H681 . C68 . C62 . 109.062 no H681 . C68 . C62 . 109.909 no C46 . C68 . C62 . 112.284(9) yes H693 . C69 . H692 . 108.306 no H693 . C69 . H691 . 109.719 no H692 . C69 . H691 . 109.892 no H693 . C69 . C67 . 109.686 no H692 . C69 . C67 . 109.766 no H691 . C69 . C67 . 109.455 no H703 . C70 . H702 . 108.985 no H703 . C70 . H701 . 109.249 no H702 . C70 . H701 . 109.256 no H703 . C70 . C67 . 110.442 no H702 . C70 . C67 . 109.632 no H701 . C70 . C67 . 109.258 no H713 . C71 . H712 . 110.229 no H713 . C71 . H711 . 108.914 no H712 . C71 . H711 . 108.596 no H713 . C71 . C67 . 110.358 no H712 . C71 . C67 . 109.791 no H711 . C71 . C67 . 108.913 no F81 . C81 . C82 . 118.369 yes F81 . C81 . C82 3_555 118.369 yes C82 . C81 . C82 3_555 123.262(7) yes C83 . C82 . H82 . 121.620 no C83 . C82 . C81 . 116.708 yes H82 . C82 . C81 . 121.664 no F82 . C83 . C84 . 116.860(8) yes F82 . C83 . C82 . 118.801(8) yes C84 . C83 . C82 . 124.328(7) yes H84 . C84 . C83 3_555 122.669 no H84 . C84 . C83 . 122.669 no C83 3_555 C84 . C83 . 114.663(8) yes C92 . C91 . C92 3_655 123.271(7) yes C92 . C91 . F91 . 118.364(8) yes C92 3_655 C91 . F91 . 118.364(8) yes C93 . C92 . H92 . 122.454 no C93 . C92 . C91 . 116.296 yes H92 . C92 . C91 . 121.248 no C94 . C93 . C92 . 124.216(7) yes C94 . C93 . F92 . 118.005(8) yes C92 . C93 . F92 . 117.779 yes H94 . C94 . C93 . 122.147 no H94 . C94 . C93 3_655 122.147 no C93 . C94 . C93 3_655 115.705(8) yes