data_bertozzi03 _audit_creation_method SHELXL-97 _chemical_name_systematic ; bertozzi03 ; _chemical_name_common EMS-VIII-007B _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51 H52 F8 O8' _chemical_formula_weight 944.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 'International Tables 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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0727 0.0534 '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 10.9513(5) _cell_length_b 14.9709(7) _cell_length_c 15.4572(7) _cell_angle_alpha 63.010(2) _cell_angle_beta 75.207(2) _cell_angle_gamma 80.666(2) _cell_volume 2180.20(17) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9788 _cell_measurement_theta_min 3.28 _cell_measurement_theta_max 67.99 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 988 _exptl_absorpt_coefficient_mu 1.012 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8882 _exptl_absorpt_correction_T_max 0.9418 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 1.0 _diffrn_refln_scan_rate 5 _space_group.centring_type primitive _space_group.IT_number 2 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'microfocus rotating anode' _diffrn_radiation_monochromator 'HELIOS multilayer mirrors' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 38046 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.28 _diffrn_reflns_theta_max 68.36 _reflns_number_total 7750 _reflns_number_gt 7242 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR-2008' _computing_structure_refinement 'SHELXL-97' _computing_molecular_graphics 'ORTEP-32' _computing_publication_material 'WinGX' _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^)+(0.0412P)^2^+1.2504P] 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 7750 _refine_ls_number_parameters 616 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0358 _refine_ls_R_factor_gt 0.0336 _refine_ls_wR_factor_ref 0.0860 _refine_ls_wR_factor_gt 0.0839 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.111 _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 C1 C 0.34288(12) 0.86017(10) -0.10609(10) 0.0153(3) Uani 1 1 d . . . C2 C 0.39801(12) 0.93482(11) -0.08373(10) 0.0194(3) Uani 1 1 d . . . C3 C 0.32135(13) 1.02758(11) -0.08127(11) 0.0226(3) Uani 1 1 d . . . H3A H 0.3753 1.0668 -0.0701 0.027 Uiso 1 1 calc R . . H3B H 0.2498 1.0059 -0.0235 0.027 Uiso 1 1 calc R . . C4 C 0.26797(13) 1.09750(11) -0.17366(12) 0.0235(3) Uani 1 1 d . . . H4A H 0.3259 1.0936 -0.2327 0.028 Uiso 1 1 calc R . . H4B H 0.2645 1.1675 -0.1822 0.028 Uiso 1 1 calc R . . C5 C 0.13388(13) 1.07121(10) -0.16786(11) 0.0207(3) Uani 1 1 d . . . H5A H 0.1159 1.0047 -0.1112 0.025 Uiso 1 1 calc R . . H5B H 0.0718 1.1210 -0.1530 0.025 Uiso 1 1 calc R . . C6 C 0.11178(12) 1.06829(10) -0.25915(10) 0.0186(3) Uani 1 1 d . . . C7 C 0.05391(13) 1.15295(11) -0.32564(11) 0.0248(3) Uani 1 1 d . . . H7 H 0.0338 1.2109 -0.3135 0.030 Uiso 1 1 calc R . . C8 C 0.02503(14) 1.15500(11) -0.40853(11) 0.0288(3) Uani 1 1 d . . . H8 H -0.0132 1.2140 -0.4529 0.035 Uiso 1 1 calc R . . C9 C 0.05212(14) 1.07083(12) -0.42642(11) 0.0275(3) Uani 1 1 d . . . H9 H 0.0313 1.0712 -0.4826 0.033 Uiso 1 1 calc R . . C10 C 0.11014(13) 0.98537(11) -0.36181(10) 0.0206(3) Uani 1 1 d . . . H10 H 0.1290 0.9276 -0.3745 0.025 Uiso 1 1 calc R . . C11 C 0.14089(12) 0.98335(10) -0.27892(10) 0.0162(3) Uani 1 1 d . . . C12 C 0.20532(12) 0.88891(10) -0.21049(9) 0.0140(3) Uani 1 1 d . . . C13 C 0.13594(12) 0.83501(9) -0.10194(9) 0.0136(3) Uani 1 1 d . . . C14 C 0.00396(12) 0.80522(10) -0.07721(9) 0.0146(3) Uani 1 1 d . . . C15 C -0.09341(12) 0.87961(10) -0.10256(10) 0.0168(3) Uani 1 1 d . . . H15 H -0.0737 0.9482 -0.1384 0.020 Uiso 1 1 calc R . . C16 C -0.21835(13) 0.85415(11) -0.07579(10) 0.0193(3) Uani 1 1 d . . . H16 H -0.2836 0.9051 -0.0936 0.023 Uiso 1 1 calc R . . C17 C -0.24780(13) 0.75417(11) -0.02309(10) 0.0209(3) Uani 1 1 d . . . H17 H -0.3334 0.7366 -0.0034 0.025 Uiso 1 1 calc R . . C18 C -0.15178(13) 0.68013(11) 0.00067(10) 0.0207(3) Uani 1 1 d . . . H18 H -0.1724 0.6117 0.0360 0.025 Uiso 1 1 calc R . . C19 C -0.02540(13) 0.70395(10) -0.02623(10) 0.0166(3) Uani 1 1 d . . . C20 C 0.07541(13) 0.62227(10) 0.00904(10) 0.0197(3) Uani 1 1 d . . . H20A H 0.1576 0.6424 -0.0375 0.024 Uiso 1 1 calc R . . H20B H 0.0536 0.5597 0.0109 0.024 Uiso 1 1 calc R . . C21 C 0.08595(14) 0.60369(11) 0.11346(11) 0.0236(3) Uani 1 1 d . . . H21A H 0.0156 0.5626 0.1625 0.028 Uiso 1 1 calc R . . H21B H 0.1660 0.5643 0.1281 0.028 Uiso 1 1 calc R . . C22 C 0.08275(13) 0.69896(11) 0.12704(10) 0.0207(3) Uani 1 1 d . . . H22A H 0.0049 0.7399 0.1086 0.025 Uiso 1 1 calc R . . H22B H 0.0765 0.6794 0.1983 0.025 Uiso 1 1 calc R . . C23 C 0.19366(13) 0.76385(10) 0.06877(10) 0.0175(3) Uani 1 1 d . . . C24 C 0.21587(12) 0.81738(9) -0.04291(9) 0.0141(3) Uani 1 1 d . . . C25 C 0.39779(12) 0.59303(10) 0.73514(9) 0.0148(3) Uani 1 1 d . . . C26 C 0.47725(12) 0.49344(10) 0.78006(10) 0.0168(3) Uani 1 1 d . . . C27 C 0.50460(13) 0.41902(10) 0.73578(11) 0.0196(3) Uani 1 1 d . . . H27A H 0.5538 0.3605 0.7770 0.023 Uiso 1 1 calc R . . H27B H 0.5592 0.4506 0.6690 0.023 Uiso 1 1 calc R . . C28 C 0.38973(13) 0.38037(10) 0.72581(10) 0.0191(3) Uani 1 1 d . . . H28A H 0.3175 0.3797 0.7798 0.023 Uiso 1 1 calc R . . H28B H 0.4098 0.3104 0.7340 0.023 Uiso 1 1 calc R . . C29 C 0.35032(12) 0.44481(10) 0.62470(10) 0.0175(3) Uani 1 1 d . . . H29A H 0.3967 0.5073 0.5906 0.021 Uiso 1 1 calc R . . H29B H 0.3779 0.4075 0.5834 0.021 Uiso 1 1 calc R . . C30 C 0.21054(12) 0.47329(10) 0.62913(9) 0.0160(3) Uani 1 1 d . . . C31 C 0.13721(13) 0.41453(10) 0.61544(9) 0.0182(3) Uani 1 1 d . . . H31 H 0.1758 0.3568 0.6066 0.022 Uiso 1 1 calc R . . C32 C 0.00963(13) 0.43793(10) 0.61432(9) 0.0193(3) Uani 1 1 d . . . H32 H -0.0383 0.3962 0.6056 0.023 Uiso 1 1 calc R . . C33 C -0.04771(13) 0.52254(11) 0.62603(10) 0.0194(3) Uani 1 1 d . . . H33 H -0.1348 0.5396 0.6247 0.023 Uiso 1 1 calc R . . C34 C 0.02338(12) 0.58215(10) 0.63979(9) 0.0170(3) Uani 1 1 d . . . H34 H -0.0159 0.6403 0.6475 0.020 Uiso 1 1 calc R . . C35 C 0.15133(12) 0.55840(10) 0.64256(9) 0.0151(3) Uani 1 1 d . . . C36 C 0.22345(12) 0.62470(10) 0.66127(9) 0.0147(3) Uani 1 1 d . . . C37 C 0.33728(12) 0.67724(9) 0.58130(9) 0.0138(3) Uani 1 1 d . . . C38 C 0.32154(12) 0.74168(10) 0.47769(9) 0.0149(3) Uani 1 1 d . . . C39 C 0.29099(12) 0.69812(10) 0.42307(10) 0.0163(3) Uani 1 1 d . . . H39 H 0.2804 0.6279 0.4528 0.020 Uiso 1 1 calc R . . C40 C 0.27603(13) 0.75628(11) 0.32621(10) 0.0193(3) Uani 1 1 d . . . H40 H 0.2574 0.7258 0.2893 0.023 Uiso 1 1 calc R . . C41 C 0.28841(13) 0.85899(11) 0.28348(10) 0.0216(3) Uani 1 1 d . . . H41 H 0.2773 0.8992 0.2174 0.026 Uiso 1 1 calc R . . C42 C 0.31707(13) 0.90297(10) 0.33742(10) 0.0202(3) Uani 1 1 d . . . H42 H 0.3245 0.9735 0.3079 0.024 Uiso 1 1 calc R . . C43 C 0.33520(12) 0.84548(10) 0.43422(10) 0.0167(3) Uani 1 1 d . . . C44 C 0.38132(13) 0.89380(10) 0.48591(10) 0.0193(3) Uani 1 1 d . . . H44A H 0.3487 0.8588 0.5584 0.023 Uiso 1 1 calc R . . H44B H 0.3488 0.9647 0.4629 0.023 Uiso 1 1 calc R . . C45 C 0.52717(13) 0.88901(11) 0.46415(11) 0.0223(3) Uani 1 1 d . . . H45A H 0.5577 0.9402 0.3960 0.027 Uiso 1 1 calc R . . H45B H 0.5546 0.9068 0.5104 0.027 Uiso 1 1 calc R . . C46 C 0.59019(13) 0.78664(11) 0.47350(10) 0.0196(3) Uani 1 1 d . . . H46A H 0.5609 0.7684 0.4284 0.023 Uiso 1 1 calc R . . H46B H 0.6827 0.7935 0.4504 0.023 Uiso 1 1 calc R . . C47 C 0.56553(12) 0.70157(10) 0.57624(10) 0.0177(3) Uani 1 1 d . . . C48 C 0.43550(12) 0.66116(9) 0.62399(9) 0.0145(3) Uani 1 1 d . . . C49 C 0.73701(13) 0.77945(11) 0.75629(10) 0.0198(3) Uani 1 1 d . . . C50 C 0.73418(15) 0.66767(11) 0.81154(11) 0.0267(3) Uani 1 1 d . . . H50A H 0.6511 0.6494 0.8556 0.040 Uiso 1 1 calc R . . H50B H 0.7999 0.6420 0.8511 0.040 Uiso 1 1 calc R . . H50C H 0.7497 0.6384 0.7642 0.040 Uiso 1 1 calc R . . C51 C 0.86237(16) 0.82191(13) 0.69874(14) 0.0377(4) Uani 1 1 d . . . H51A H 0.8529 0.8954 0.6685 0.057 Uiso 1 1 calc R . . H51B H 0.8947 0.7989 0.6466 0.057 Uiso 1 1 calc R . . H51C H 0.9219 0.7994 0.7433 0.057 Uiso 1 1 calc R . . O1 O 0.31904(8) 0.91692(7) -0.20293(7) 0.01477(19) Uani 1 1 d . . . O2 O 0.43071(8) 0.78008(7) -0.10214(7) 0.0180(2) Uani 1 1 d . . . H2 H 0.4943 0.8013 -0.1482 0.027 Uiso 1 1 calc R . . O3 O 0.23241(9) 0.81970(7) -0.25253(7) 0.01632(19) Uani 1 1 d . . . H3 H 0.2864 0.7756 -0.2259 0.024 Uiso 1 1 calc R . . O4 O 0.27671(8) 0.56190(7) 0.74632(6) 0.01553(19) Uani 1 1 d . . . O5 O 0.39216(9) 0.64925(7) 0.78788(7) 0.01692(19) Uani 1 1 d . . . H5 H 0.3889 0.6104 0.8482 0.025 Uiso 1 1 calc R . . O6 O 0.13628(8) 0.69769(7) 0.67883(7) 0.0178(2) Uani 1 1 d . . . H6 H 0.1714 0.7305 0.6968 0.027 Uiso 1 1 calc R . . O7 O 0.64278(9) 0.83475(8) 0.75835(8) 0.0232(2) Uani 1 1 d . . . O8 O 0.39922(11) 0.57551(8) 0.98107(8) 0.0304(3) Uani 1 1 d D . . F1 F 0.43761(8) 0.88193(6) 0.00430(6) 0.02486(19) Uani 1 1 d . . . F2 F 0.50718(7) 0.96467(6) -0.15469(6) 0.02374(18) Uani 1 1 d . . . F3 F 0.30189(7) 0.70734(6) 0.09552(6) 0.02314(18) Uani 1 1 d . . . F4 F 0.18236(8) 0.83696(6) 0.10292(6) 0.02343(18) Uani 1 1 d . . . F5 F 0.59082(7) 0.51673(6) 0.78507(6) 0.01967(17) Uani 1 1 d . . . F6 F 0.41533(7) 0.44576(6) 0.87778(6) 0.02011(17) Uani 1 1 d . . . F7 F 0.64771(7) 0.62084(6) 0.57331(6) 0.02485(19) Uani 1 1 d . . . F8 F 0.60492(8) 0.72751(7) 0.63873(6) 0.02654(19) Uani 1 1 d . . . H8X H 0.4117(18) 0.6322(7) 0.9734(14) 0.032 Uiso 1 1 d D . . H8Y H 0.3926(18) 0.5485(13) 1.0420(4) 0.032 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0146(6) 0.0154(7) 0.0172(6) -0.0084(5) -0.0032(5) 0.0001(5) C2 0.0150(6) 0.0230(7) 0.0237(7) -0.0127(6) -0.0038(5) -0.0028(5) C3 0.0196(7) 0.0238(8) 0.0330(8) -0.0198(6) -0.0031(6) -0.0041(6) C4 0.0220(7) 0.0160(7) 0.0350(8) -0.0138(6) -0.0034(6) -0.0032(5) C5 0.0181(7) 0.0152(7) 0.0303(8) -0.0128(6) -0.0026(6) 0.0006(5) C6 0.0134(6) 0.0143(7) 0.0232(7) -0.0054(5) 0.0002(5) -0.0026(5) C7 0.0191(7) 0.0138(7) 0.0324(8) -0.0048(6) -0.0010(6) -0.0003(5) C8 0.0236(7) 0.0204(8) 0.0267(8) 0.0024(6) -0.0058(6) 0.0026(6) C9 0.0267(8) 0.0289(8) 0.0194(7) -0.0033(6) -0.0072(6) 0.0010(6) C10 0.0199(7) 0.0200(7) 0.0178(6) -0.0056(5) -0.0025(5) -0.0004(5) C11 0.0129(6) 0.0145(7) 0.0164(6) -0.0036(5) -0.0003(5) -0.0020(5) C12 0.0132(6) 0.0126(6) 0.0173(6) -0.0076(5) -0.0024(5) -0.0011(5) C13 0.0158(6) 0.0095(6) 0.0155(6) -0.0064(5) -0.0021(5) 0.0000(5) C14 0.0151(6) 0.0175(7) 0.0133(6) -0.0078(5) -0.0027(5) -0.0027(5) C15 0.0179(6) 0.0164(7) 0.0170(6) -0.0076(5) -0.0036(5) -0.0019(5) C16 0.0161(6) 0.0241(7) 0.0202(7) -0.0117(6) -0.0049(5) 0.0006(5) C17 0.0158(6) 0.0288(8) 0.0211(7) -0.0128(6) -0.0018(5) -0.0063(5) C18 0.0222(7) 0.0197(7) 0.0211(7) -0.0088(6) -0.0020(5) -0.0075(5) C19 0.0190(6) 0.0170(7) 0.0157(6) -0.0085(5) -0.0027(5) -0.0027(5) C20 0.0212(7) 0.0139(7) 0.0232(7) -0.0072(5) -0.0038(5) -0.0024(5) C21 0.0249(7) 0.0180(7) 0.0213(7) -0.0020(6) -0.0052(6) -0.0029(5) C22 0.0220(7) 0.0230(7) 0.0141(6) -0.0058(5) -0.0030(5) -0.0018(5) C23 0.0183(6) 0.0193(7) 0.0175(6) -0.0099(5) -0.0065(5) 0.0024(5) C24 0.0145(6) 0.0110(6) 0.0178(6) -0.0077(5) -0.0027(5) -0.0001(5) C25 0.0155(6) 0.0146(7) 0.0164(6) -0.0082(5) -0.0036(5) -0.0010(5) C26 0.0168(6) 0.0167(7) 0.0179(6) -0.0071(5) -0.0057(5) -0.0013(5) C27 0.0200(7) 0.0160(7) 0.0258(7) -0.0113(6) -0.0086(5) 0.0039(5) C28 0.0222(7) 0.0130(7) 0.0244(7) -0.0091(5) -0.0075(5) 0.0008(5) C29 0.0184(7) 0.0156(7) 0.0213(7) -0.0107(5) -0.0040(5) 0.0000(5) C30 0.0181(6) 0.0150(7) 0.0136(6) -0.0049(5) -0.0027(5) -0.0023(5) C31 0.0244(7) 0.0145(7) 0.0150(6) -0.0054(5) -0.0035(5) -0.0034(5) C32 0.0234(7) 0.0197(7) 0.0141(6) -0.0037(5) -0.0049(5) -0.0088(5) C33 0.0167(6) 0.0226(7) 0.0162(6) -0.0046(5) -0.0052(5) -0.0031(5) C34 0.0173(6) 0.0168(7) 0.0137(6) -0.0042(5) -0.0028(5) -0.0006(5) C35 0.0167(6) 0.0144(6) 0.0119(6) -0.0034(5) -0.0026(5) -0.0029(5) C36 0.0158(6) 0.0130(6) 0.0150(6) -0.0062(5) -0.0038(5) 0.0012(5) C37 0.0159(6) 0.0105(6) 0.0168(6) -0.0082(5) -0.0023(5) -0.0002(5) C38 0.0124(6) 0.0156(7) 0.0160(6) -0.0070(5) -0.0019(5) 0.0000(5) C39 0.0154(6) 0.0144(7) 0.0191(6) -0.0074(5) -0.0030(5) -0.0008(5) C40 0.0188(7) 0.0226(7) 0.0195(7) -0.0112(6) -0.0057(5) 0.0002(5) C41 0.0230(7) 0.0212(7) 0.0164(6) -0.0043(5) -0.0056(5) 0.0008(5) C42 0.0214(7) 0.0139(7) 0.0206(7) -0.0044(5) -0.0029(5) -0.0005(5) C43 0.0143(6) 0.0166(7) 0.0184(6) -0.0084(5) -0.0013(5) 0.0001(5) C44 0.0239(7) 0.0137(7) 0.0205(7) -0.0082(5) -0.0026(5) -0.0021(5) C45 0.0243(7) 0.0187(7) 0.0246(7) -0.0086(6) -0.0043(6) -0.0068(5) C46 0.0166(6) 0.0225(7) 0.0207(7) -0.0105(6) -0.0011(5) -0.0047(5) C47 0.0160(6) 0.0199(7) 0.0210(7) -0.0114(6) -0.0051(5) -0.0006(5) C48 0.0178(6) 0.0113(6) 0.0160(6) -0.0078(5) -0.0032(5) -0.0001(5) C49 0.0223(7) 0.0221(7) 0.0196(7) -0.0131(6) -0.0048(5) 0.0000(6) C50 0.0331(8) 0.0212(8) 0.0291(8) -0.0122(6) -0.0100(6) -0.0002(6) C51 0.0279(8) 0.0286(9) 0.0467(10) -0.0165(8) 0.0086(7) -0.0010(7) O1 0.0129(4) 0.0144(5) 0.0167(4) -0.0065(4) -0.0020(3) -0.0021(3) O2 0.0140(4) 0.0174(5) 0.0222(5) -0.0096(4) -0.0026(4) 0.0015(4) O3 0.0189(5) 0.0152(5) 0.0174(4) -0.0094(4) -0.0058(4) 0.0027(3) O4 0.0155(4) 0.0158(5) 0.0149(4) -0.0055(4) -0.0039(3) -0.0018(3) O5 0.0237(5) 0.0141(5) 0.0151(4) -0.0077(4) -0.0061(4) 0.0010(4) O6 0.0159(4) 0.0180(5) 0.0239(5) -0.0132(4) -0.0050(4) 0.0021(4) O7 0.0200(5) 0.0230(5) 0.0281(5) -0.0139(4) -0.0036(4) 0.0011(4) O8 0.0434(7) 0.0211(6) 0.0193(5) -0.0066(4) -0.0044(5) 0.0085(5) F1 0.0232(4) 0.0308(5) 0.0291(4) -0.0173(4) -0.0113(3) -0.0009(3) F2 0.0144(4) 0.0268(5) 0.0338(5) -0.0176(4) 0.0003(3) -0.0057(3) F3 0.0209(4) 0.0270(4) 0.0202(4) -0.0077(3) -0.0099(3) 0.0037(3) F4 0.0275(4) 0.0280(5) 0.0213(4) -0.0161(3) -0.0045(3) -0.0026(3) F5 0.0185(4) 0.0182(4) 0.0258(4) -0.0099(3) -0.0104(3) 0.0005(3) F6 0.0255(4) 0.0155(4) 0.0170(4) -0.0044(3) -0.0056(3) -0.0010(3) F7 0.0169(4) 0.0240(4) 0.0284(4) -0.0090(3) -0.0033(3) 0.0034(3) F8 0.0272(4) 0.0352(5) 0.0227(4) -0.0130(4) -0.0068(3) -0.0121(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 O2 1.3985(15) . ? C1 O1 1.4156(16) . ? C1 C24 1.5252(17) . ? C1 C2 1.5522(18) . ? C2 F1 1.3706(16) . ? C2 F2 1.3752(16) . ? C2 C3 1.5126(19) . ? C3 C4 1.532(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5516(19) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.512(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.398(2) . ? C6 C11 1.408(2) . ? C7 C8 1.382(2) . ? C7 H7 0.9500 . ? C8 C9 1.380(2) . ? C8 H8 0.9500 . ? C9 C10 1.392(2) . ? C9 H9 0.9500 . ? C10 C11 1.392(2) . ? C10 H10 0.9500 . ? C11 C12 1.5218(17) . ? C12 O3 1.4131(15) . ? C12 O1 1.4243(15) . ? C12 C13 1.5372(17) . ? C13 C24 1.3353(18) . ? C13 C14 1.4854(17) . ? C14 C15 1.4011(18) . ? C14 C19 1.4025(19) . ? C15 C16 1.3876(19) . ? C15 H15 0.9500 . ? C16 C17 1.387(2) . ? C16 H16 0.9500 . ? C17 C18 1.385(2) . ? C17 H17 0.9500 . ? C18 C19 1.3954(19) . ? C18 H18 0.9500 . ? C19 C20 1.5085(19) . ? C20 C21 1.541(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.527(2) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.5033(19) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 F3 1.3780(15) . ? C23 F4 1.3924(16) . ? C23 C24 1.5081(18) . ? C25 O5 1.3991(15) . ? C25 O4 1.4197(15) . ? C25 C48 1.5317(17) . ? C25 C26 1.5524(18) . ? C26 F5 1.3743(15) . ? C26 F6 1.3806(15) . ? C26 C27 1.5097(18) . ? C27 C28 1.5353(19) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.5493(18) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.5137(18) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.3958(19) . ? C30 C35 1.4108(19) . ? C31 C32 1.387(2) . ? C31 H31 0.9500 . ? C32 C33 1.387(2) . ? C32 H32 0.9500 . ? C33 C34 1.389(2) . ? C33 H33 0.9500 . ? C34 C35 1.3953(19) . ? C34 H34 0.9500 . ? C35 C36 1.5245(18) . ? C36 O6 1.4063(15) . ? C36 O4 1.4297(15) . ? C36 C37 1.5328(18) . ? C37 C48 1.3360(19) . ? C37 C38 1.4866(18) . ? C38 C39 1.4016(18) . ? C38 C43 1.402(2) . ? C39 C40 1.3865(19) . ? C39 H39 0.9500 . ? C40 C41 1.385(2) . ? C40 H40 0.9500 . ? C41 C42 1.388(2) . ? C41 H41 0.9500 . ? C42 C43 1.3950(19) . ? C42 H42 0.9500 . ? C43 C44 1.5053(19) . ? C44 C45 1.5428(19) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 C46 1.534(2) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 C47 1.5078(19) . ? C46 H46A 0.9900 . ? C46 H46B 0.9900 . ? C47 F8 1.3702(15) . ? C47 F7 1.3960(16) . ? C47 C48 1.5086(18) . ? C49 O7 1.2172(17) . ? C49 C51 1.492(2) . ? C49 C50 1.496(2) . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? C51 H51A 0.9800 . ? C51 H51B 0.9800 . ? C51 H51C 0.9800 . ? O2 H2 0.8400 . ? O3 H3 0.8400 . ? O5 H5 0.8400 . ? O6 H6 0.8400 . ? O8 H8X 0.832(5) . ? O8 H8Y 0.827(5) . ? 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 O2 C1 O1 111.07(10) . . ? O2 C1 C24 108.33(10) . . ? O1 C1 C24 104.19(10) . . ? O2 C1 C2 110.04(10) . . ? O1 C1 C2 105.02(10) . . ? C24 C1 C2 117.96(11) . . ? F1 C2 F2 104.94(10) . . ? F1 C2 C3 108.27(11) . . ? F2 C2 C3 108.30(11) . . ? F1 C2 C1 108.14(11) . . ? F2 C2 C1 105.01(10) . . ? C3 C2 C1 121.05(11) . . ? C2 C3 C4 116.51(12) . . ? C2 C3 H3A 108.2 . . ? C4 C3 H3A 108.2 . . ? C2 C3 H3B 108.2 . . ? C4 C3 H3B 108.2 . . ? H3A C3 H3B 107.3 . . ? C3 C4 C5 112.93(12) . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C6 C5 C4 116.48(12) . . ? C6 C5 H5A 108.2 . . ? C4 C5 H5A 108.2 . . ? C6 C5 H5B 108.2 . . ? C4 C5 H5B 108.2 . . ? H5A C5 H5B 107.3 . . ? C7 C6 C11 117.88(13) . . ? C7 C6 C5 118.35(13) . . ? C11 C6 C5 123.71(12) . . ? C8 C7 C6 122.10(14) . . ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? C9 C8 C7 119.58(14) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 119.74(14) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 120.89(14) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C6 119.79(12) . . ? C10 C11 C12 119.39(12) . . ? C6 C11 C12 120.82(12) . . ? O3 C12 O1 110.55(10) . . ? O3 C12 C11 108.53(10) . . ? O1 C12 C11 107.60(10) . . ? O3 C12 C13 108.48(10) . . ? O1 C12 C13 103.63(10) . . ? C11 C12 C13 117.90(10) . . ? C24 C13 C14 130.27(12) . . ? C24 C13 C12 108.75(11) . . ? C14 C13 C12 120.85(11) . . ? C15 C14 C19 119.41(12) . . ? C15 C14 C13 119.47(12) . . ? C19 C14 C13 121.10(12) . . ? C16 C15 C14 120.69(13) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 119.93(13) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C18 C17 C16 119.67(13) . . ? C18 C17 H17 120.2 . . ? C16 C17 H17 120.2 . . ? C17 C18 C19 121.37(13) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C18 C19 C14 118.90(13) . . ? C18 C19 C20 119.88(12) . . ? C14 C19 C20 120.88(12) . . ? C19 C20 C21 109.64(11) . . ? C19 C20 H20A 109.7 . . ? C21 C20 H20A 109.7 . . ? C19 C20 H20B 109.7 . . ? C21 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C22 C21 C20 114.52(11) . . ? C22 C21 H21A 108.6 . . ? C20 C21 H21A 108.6 . . ? C22 C21 H21B 108.6 . . ? C20 C21 H21B 108.6 . . ? H21A C21 H21B 107.6 . . ? C23 C22 C21 116.16(12) . . ? C23 C22 H22A 108.2 . . ? C21 C22 H22A 108.2 . . ? C23 C22 H22B 108.2 . . ? C21 C22 H22B 108.2 . . ? H22A C22 H22B 107.4 . . ? F3 C23 F4 104.41(10) . . ? F3 C23 C22 108.26(11) . . ? F4 C23 C22 106.98(11) . . ? F3 C23 C24 108.70(10) . . ? F4 C23 C24 107.03(11) . . ? C22 C23 C24 120.34(11) . . ? C13 C24 C23 128.76(12) . . ? C13 C24 C1 109.41(11) . . ? C23 C24 C1 121.83(11) . . ? O5 C25 O4 111.59(10) . . ? O5 C25 C48 108.71(10) . . ? O4 C25 C48 104.03(10) . . ? O5 C25 C26 109.49(10) . . ? O4 C25 C26 104.31(10) . . ? C48 C25 C26 118.51(11) . . ? F5 C26 F6 104.58(10) . . ? F5 C26 C27 107.84(10) . . ? F6 C26 C27 108.51(11) . . ? F5 C26 C25 108.02(10) . . ? F6 C26 C25 105.00(10) . . ? C27 C26 C25 121.65(11) . . ? C26 C27 C28 116.61(11) . . ? C26 C27 H27A 108.1 . . ? C28 C27 H27A 108.1 . . ? C26 C27 H27B 108.1 . . ? C28 C27 H27B 108.1 . . ? H27A C27 H27B 107.3 . . ? C27 C28 C29 113.04(11) . . ? C27 C28 H28A 109.0 . . ? C29 C28 H28A 109.0 . . ? C27 C28 H28B 109.0 . . ? C29 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C30 C29 C28 115.96(11) . . ? C30 C29 H29A 108.3 . . ? C28 C29 H29A 108.3 . . ? C30 C29 H29B 108.3 . . ? C28 C29 H29B 108.3 . . ? H29A C29 H29B 107.4 . . ? C31 C30 C35 118.19(12) . . ? C31 C30 C29 118.34(12) . . ? C35 C30 C29 123.42(12) . . ? C32 C31 C30 121.92(13) . . ? C32 C31 H31 119.0 . . ? C30 C31 H31 119.0 . . ? C31 C32 C33 119.68(12) . . ? C31 C32 H32 120.2 . . ? C33 C32 H32 120.2 . . ? C32 C33 C34 119.42(12) . . ? C32 C33 H33 120.3 . . ? C34 C33 H33 120.3 . . ? C33 C34 C35 121.34(13) . . ? C33 C34 H34 119.3 . . ? C35 C34 H34 119.3 . . ? C34 C35 C30 119.44(12) . . ? C34 C35 C36 118.99(12) . . ? C30 C35 C36 121.57(11) . . ? O6 C36 O4 111.05(10) . . ? O6 C36 C35 107.52(10) . . ? O4 C36 C35 107.58(10) . . ? O6 C36 C37 108.82(10) . . ? O4 C36 C37 103.78(10) . . ? C35 C36 C37 118.04(10) . . ? C48 C37 C38 131.06(12) . . ? C48 C37 C36 108.96(11) . . ? C38 C37 C36 119.68(11) . . ? C39 C38 C43 119.51(12) . . ? C39 C38 C37 119.46(12) . . ? C43 C38 C37 121.03(12) . . ? C40 C39 C38 120.76(12) . . ? C40 C39 H39 119.6 . . ? C38 C39 H39 119.6 . . ? C41 C40 C39 119.77(13) . . ? C41 C40 H40 120.1 . . ? C39 C40 H40 120.1 . . ? C40 C41 C42 119.87(13) . . ? C40 C41 H41 120.1 . . ? C42 C41 H41 120.1 . . ? C41 C42 C43 121.24(13) . . ? C41 C42 H42 119.4 . . ? C43 C42 H42 119.4 . . ? C42 C43 C38 118.83(12) . . ? C42 C43 C44 119.64(12) . . ? C38 C43 C44 121.24(12) . . ? C43 C44 C45 110.51(11) . . ? C43 C44 H44A 109.5 . . ? C45 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? C45 C44 H44B 109.5 . . ? H44A C44 H44B 108.1 . . ? C46 C45 C44 114.66(11) . . ? C46 C45 H45A 108.6 . . ? C44 C45 H45A 108.6 . . ? C46 C45 H45B 108.6 . . ? C44 C45 H45B 108.6 . . ? H45A C45 H45B 107.6 . . ? C47 C46 C45 115.66(11) . . ? C47 C46 H46A 108.4 . . ? C45 C46 H46A 108.4 . . ? C47 C46 H46B 108.4 . . ? C45 C46 H46B 108.4 . . ? H46A C46 H46B 107.4 . . ? F8 C47 F7 104.33(10) . . ? F8 C47 C46 108.23(11) . . ? F7 C47 C46 106.98(11) . . ? F8 C47 C48 109.01(10) . . ? F7 C47 C48 106.54(11) . . ? C46 C47 C48 120.57(11) . . ? C37 C48 C47 128.25(12) . . ? C37 C48 C25 109.48(11) . . ? C47 C48 C25 122.26(11) . . ? O7 C49 C51 120.45(14) . . ? O7 C49 C50 122.53(13) . . ? C51 C49 C50 117.02(13) . . ? C49 C50 H50A 109.5 . . ? C49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C49 C51 H51A 109.5 . . ? C49 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C49 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? C1 O1 C12 110.73(9) . . ? C1 O2 H2 109.5 . . ? C12 O3 H3 109.5 . . ? C25 O4 C36 110.81(9) . . ? C25 O5 H5 109.5 . . ? C36 O6 H6 109.5 . . ? H8X O8 H8Y 95.4(18) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 67.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.347 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.046